Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229615024080/uk3121sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229615024080/uk3121Iasup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229615024080/uk3121Ibsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229615024080/uk3121IIsup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229615024080/uk3121IIIsup5.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229615024080/uk3121IVsup6.hkl |
CCDC references: 1442480; 1442479; 1442478; 1442477; 1442476
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 DA–AD (D denotes a donor and A an acceptor) or DD–AA pattern, or three hydrogen bonds with DDA–AAD or DAD–ADA 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).
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.
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).
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 ADA–DAD (synthon 3s) or an unsymmetric AAD–DDA (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 A–D. 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 A–M) 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 A–F and G–M, 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 A–F are arranged parallel to [211], while the chains built by molecules G–M 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 G–M 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 A–B–B–A 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.
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 DA–AD (D denotes a donor and A an acceptor) or DD–AA pattern, or three hydrogen bonds with DDA–AAD or DAD–ADA 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 ADA–DAD (synthon 3s) or an unsymmetric AAD–DDA (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 A–D. 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 A–M) 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 A–F and G–M, 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 A–F are arranged parallel to [211], while the chains built by molecules G–M 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 G–M 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 A–B–B–A 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.
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.
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).
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).
C5H7N2+·C4H3ClN3O−·3C4H4ClN3O | Z = 2 |
Mr = 676.32 | F(000) = 692 |
Triclinic, P1 | Dx = 1.651 Mg m−3 |
a = 10.8229 (11) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.7395 (14) Å | Cell parameters from 11802 reflections |
c = 12.7637 (13) Å | θ = 3.3–26.3° |
α = 62.633 (8)° | µ = 0.50 mm−1 |
β = 70.877 (8)° | T = 173 K |
γ = 81.182 (9)° | Plate, colourless |
V = 1360.7 (3) Å3 | 0.26 × 0.09 × 0.07 mm |
Stoe IPDSII two-circle diffractometer | 3077 reflections with I > 2σ(I) |
Radiation source: Genix 3D IµS microfocus X-ray source | Rint = 0.125 |
ω scans | θmax = 25.9°, θmin = 3.3° |
Absorption correction: multi-scan X-AREA (Stoe & Cie, 2001) | h = −13→13 |
Tmin = 0.880, Tmax = 0.960 | k = −14→14 |
22097 measured reflections | l = −15→15 |
5228 independent reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.058 | Hydrogen site location: mixed |
wR(F2) = 0.149 | H 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 parameters | Δρmax = 0.42 e Å−3 |
14 restraints | Δρmin = −0.43 e Å−3 |
C5H7N2+·C4H3ClN3O−·3C4H4ClN3O | γ = 81.182 (9)° |
Mr = 676.32 | V = 1360.7 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 10.8229 (11) Å | Mo Kα radiation |
b = 11.7395 (14) Å | µ = 0.50 mm−1 |
c = 12.7637 (13) Å | T = 173 K |
α = 62.633 (8)° | 0.26 × 0.09 × 0.07 mm |
β = 70.877 (8)° |
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 = 0.960 | Rint = 0.125 |
22097 measured reflections |
R[F2 > 2σ(F2)] = 0.058 | 14 restraints |
wR(F2) = 0.149 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.92 | Δρmax = 0.42 e Å−3 |
5228 reflections | Δρmin = −0.43 e Å−3 |
430 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
N1A | 0.5541 (3) | 0.3919 (3) | 0.8172 (3) | 0.0302 (7) | |
C2A | 0.4893 (3) | 0.4800 (4) | 0.7403 (4) | 0.0305 (8) | |
N2A | 0.4876 (3) | 0.5997 (3) | 0.7272 (4) | 0.0384 (8) | |
H21A | 0.456 (4) | 0.667 (3) | 0.674 (3) | 0.046* | |
H22A | 0.532 (4) | 0.605 (4) | 0.771 (4) | 0.046* | |
N3A | 0.4248 (3) | 0.4576 (3) | 0.6771 (3) | 0.0278 (7) | |
C4A | 0.4232 (3) | 0.3365 (4) | 0.6933 (4) | 0.0287 (8) | |
O4A | 0.3569 (3) | 0.3127 (3) | 0.6368 (3) | 0.0362 (7) | |
C5A | 0.4907 (3) | 0.2389 (4) | 0.7693 (4) | 0.0306 (8) | |
H5A | 0.4931 | 0.1531 | 0.7798 | 0.037* | |
C6A | 0.5522 (3) | 0.2743 (4) | 0.8267 (3) | 0.0284 (8) | |
Cl6A | 0.63910 (9) | 0.16052 (10) | 0.92239 (10) | 0.0375 (3) | |
N1B | 0.1553 (3) | 0.7179 (3) | 0.3900 (3) | 0.0295 (7) | |
C2B | 0.2268 (3) | 0.6322 (4) | 0.4590 (4) | 0.0277 (8) | |
N2B | 0.2281 (3) | 0.5110 (3) | 0.4790 (3) | 0.0318 (7) | |
H21B | 0.187 (3) | 0.499 (4) | 0.436 (4) | 0.038* | |
H22B | 0.270 (4) | 0.450 (3) | 0.529 (3) | 0.038* | |
N3B | 0.2981 (3) | 0.6644 (3) | 0.5124 (3) | 0.0275 (7) | |
H3B | 0.347 (3) | 0.603 (3) | 0.552 (3) | 0.033* | |
C4B | 0.3078 (3) | 0.7883 (4) | 0.4928 (4) | 0.0295 (8) | |
O4B | 0.3812 (2) | 0.8121 (2) | 0.5385 (3) | 0.0327 (6) | |
C5B | 0.2298 (3) | 0.8801 (4) | 0.4224 (4) | 0.0333 (9) | |
H5B | 0.2260 | 0.9670 | 0.4089 | 0.040* | |
C6B | 0.1607 (3) | 0.8381 (4) | 0.3750 (4) | 0.0310 (9) | |
Cl6B | 0.06668 (9) | 0.94686 (9) | 0.28506 (10) | 0.0400 (3) | |
N1C | 0.6284 (3) | 0.6441 (3) | 0.8735 (3) | 0.0295 (7) | |
C2C | 0.6923 (3) | 0.5555 (4) | 0.9476 (3) | 0.0262 (8) | |
N2C | 0.6971 (3) | 0.4350 (3) | 0.9613 (3) | 0.0344 (8) | |
H21C | 0.650 (3) | 0.425 (4) | 0.921 (4) | 0.041* | |
H22C | 0.717 (4) | 0.373 (3) | 1.026 (3) | 0.041* | |
N3C | 0.7574 (3) | 0.5832 (3) | 1.0080 (3) | 0.0287 (7) | |
H3C | 0.804 (4) | 0.521 (3) | 1.050 (3) | 0.034* | |
C4C | 0.7642 (3) | 0.7063 (4) | 0.9953 (3) | 0.0263 (8) | |
O4C | 0.8291 (2) | 0.7227 (2) | 1.0520 (3) | 0.0325 (6) | |
C5C | 0.6956 (3) | 0.8006 (4) | 0.9168 (4) | 0.0314 (9) | |
H5C | 0.6942 | 0.8877 | 0.9021 | 0.038* | |
C6C | 0.6321 (3) | 0.7622 (4) | 0.8633 (3) | 0.0286 (8) | |
Cl6C | 0.54311 (9) | 0.87294 (10) | 0.76902 (10) | 0.0377 (3) | |
N1D | 0.0838 (3) | 0.4633 (3) | 0.3370 (3) | 0.0300 (7) | |
C2D | 0.0142 (3) | 0.5503 (4) | 0.2695 (4) | 0.0296 (8) | |
N2D | 0.0095 (3) | 0.6703 (3) | 0.2564 (4) | 0.0385 (8) | |
H21D | 0.046 (4) | 0.681 (4) | 0.304 (4) | 0.046* | |
H22D | −0.039 (4) | 0.729 (3) | 0.215 (4) | 0.046* | |
N3D | −0.0505 (3) | 0.5239 (3) | 0.2085 (3) | 0.0310 (7) | |
H3D | −0.092 (4) | 0.592 (3) | 0.164 (3) | 0.037* | |
C4D | −0.0500 (3) | 0.4055 (4) | 0.2115 (4) | 0.0307 (8) | |
O4D | −0.1115 (3) | 0.3893 (3) | 0.1522 (3) | 0.0406 (7) | |
C5D | 0.0224 (3) | 0.3107 (4) | 0.2854 (4) | 0.0324 (9) | |
H5D | 0.0274 | 0.2251 | 0.2951 | 0.039* | |
C6D | 0.0846 (3) | 0.3467 (4) | 0.3418 (4) | 0.0303 (9) | |
Cl6D | 0.17609 (9) | 0.23424 (10) | 0.43204 (10) | 0.0375 (3) | |
N1E | 0.2719 (3) | 0.0830 (3) | 0.7469 (3) | 0.0299 (7) | |
H1E | 0.315 (3) | 0.156 (2) | 0.697 (3) | 0.036* | |
C2E | 0.2825 (3) | 0.0046 (4) | 0.6931 (4) | 0.0292 (8) | |
N2E | 0.3585 (3) | 0.0405 (3) | 0.5774 (3) | 0.0336 (8) | |
H21E | 0.372 (4) | −0.014 (3) | 0.548 (4) | 0.040* | |
H22E | 0.416 (3) | 0.103 (3) | 0.543 (4) | 0.040* | |
C3E | 0.2128 (3) | −0.1108 (3) | 0.7621 (4) | 0.0294 (8) | |
H3E | 0.2168 | −0.1667 | 0.7259 | 0.035* | |
C4E | 0.1394 (3) | −0.1429 (4) | 0.8807 (4) | 0.0348 (9) | |
H4E | 0.0901 | −0.2200 | 0.9268 | 0.042* | |
C5E | 0.1366 (3) | −0.0623 (4) | 0.9353 (4) | 0.0345 (9) | |
H5E | 0.0897 | −0.0858 | 1.0195 | 0.041* | |
C6E | 0.2023 (4) | 0.0501 (4) | 0.8647 (4) | 0.0347 (9) | |
H6E | 0.1989 | 0.1070 | 0.8997 | 0.042* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1A | 0.0285 (15) | 0.0341 (18) | 0.034 (2) | −0.0005 (13) | −0.0137 (14) | −0.0166 (16) |
C2A | 0.0228 (17) | 0.039 (2) | 0.032 (2) | −0.0021 (16) | −0.0078 (16) | −0.0171 (19) |
N2A | 0.049 (2) | 0.0333 (19) | 0.048 (2) | 0.0001 (16) | −0.0306 (17) | −0.0193 (18) |
N3A | 0.0276 (14) | 0.0322 (17) | 0.0307 (19) | −0.0014 (13) | −0.0136 (13) | −0.0157 (15) |
C4A | 0.0266 (17) | 0.036 (2) | 0.026 (2) | −0.0046 (15) | −0.0069 (15) | −0.0142 (18) |
O4A | 0.0442 (15) | 0.0332 (15) | 0.0453 (19) | 0.0002 (12) | −0.0267 (14) | −0.0198 (14) |
C5A | 0.0276 (17) | 0.035 (2) | 0.037 (2) | −0.0003 (16) | −0.0119 (16) | −0.0210 (19) |
C6A | 0.0217 (16) | 0.035 (2) | 0.028 (2) | 0.0019 (15) | −0.0067 (15) | −0.0141 (18) |
Cl6A | 0.0345 (5) | 0.0423 (6) | 0.0405 (6) | 0.0073 (4) | −0.0197 (4) | −0.0184 (5) |
N1B | 0.0252 (14) | 0.0353 (18) | 0.032 (2) | −0.0018 (13) | −0.0106 (13) | −0.0158 (16) |
C2B | 0.0222 (16) | 0.036 (2) | 0.028 (2) | −0.0026 (15) | −0.0059 (15) | −0.0162 (18) |
N2B | 0.0348 (17) | 0.0319 (18) | 0.038 (2) | −0.0013 (14) | −0.0193 (15) | −0.0168 (17) |
N3B | 0.0251 (14) | 0.0294 (17) | 0.0320 (19) | −0.0001 (12) | −0.0103 (13) | −0.0155 (15) |
C4B | 0.0283 (18) | 0.031 (2) | 0.030 (2) | −0.0025 (15) | −0.0040 (16) | −0.0162 (18) |
O4B | 0.0342 (13) | 0.0349 (15) | 0.0374 (17) | −0.0035 (11) | −0.0151 (12) | −0.0187 (13) |
C5B | 0.0295 (18) | 0.034 (2) | 0.044 (3) | 0.0025 (16) | −0.0145 (17) | −0.021 (2) |
C6B | 0.0212 (16) | 0.034 (2) | 0.034 (2) | 0.0001 (15) | −0.0032 (15) | −0.0148 (19) |
Cl6B | 0.0338 (5) | 0.0362 (5) | 0.0501 (7) | 0.0031 (4) | −0.0208 (5) | −0.0143 (5) |
N1C | 0.0240 (14) | 0.0344 (18) | 0.032 (2) | −0.0016 (13) | −0.0095 (13) | −0.0148 (15) |
C2C | 0.0217 (16) | 0.033 (2) | 0.026 (2) | −0.0029 (15) | −0.0066 (15) | −0.0139 (17) |
N2C | 0.0408 (18) | 0.0323 (19) | 0.039 (2) | −0.0010 (15) | −0.0211 (16) | −0.0165 (17) |
N3C | 0.0257 (15) | 0.0307 (17) | 0.033 (2) | 0.0006 (13) | −0.0118 (13) | −0.0150 (16) |
C4C | 0.0227 (16) | 0.032 (2) | 0.027 (2) | −0.0036 (14) | −0.0069 (15) | −0.0139 (17) |
O4C | 0.0339 (13) | 0.0342 (15) | 0.0409 (17) | 0.0000 (11) | −0.0177 (12) | −0.0213 (14) |
C5C | 0.0265 (17) | 0.032 (2) | 0.037 (2) | −0.0009 (16) | −0.0100 (16) | −0.0160 (19) |
C6C | 0.0221 (16) | 0.036 (2) | 0.025 (2) | 0.0014 (15) | −0.0056 (15) | −0.0125 (18) |
Cl6C | 0.0346 (5) | 0.0406 (6) | 0.0413 (6) | 0.0052 (4) | −0.0198 (4) | −0.0165 (5) |
N1D | 0.0259 (15) | 0.0314 (17) | 0.034 (2) | 0.0008 (13) | −0.0144 (14) | −0.0123 (15) |
C2D | 0.0254 (17) | 0.034 (2) | 0.029 (2) | −0.0028 (15) | −0.0081 (16) | −0.0133 (18) |
N2D | 0.048 (2) | 0.0325 (19) | 0.048 (2) | 0.0016 (15) | −0.0288 (17) | −0.0183 (18) |
N3D | 0.0332 (16) | 0.0292 (17) | 0.037 (2) | 0.0023 (14) | −0.0196 (15) | −0.0147 (16) |
C4D | 0.0267 (17) | 0.035 (2) | 0.031 (2) | −0.0052 (15) | −0.0074 (16) | −0.0144 (18) |
O4D | 0.0445 (15) | 0.0409 (16) | 0.055 (2) | 0.0024 (13) | −0.0313 (14) | −0.0259 (16) |
C5D | 0.0273 (18) | 0.035 (2) | 0.037 (2) | 0.0014 (16) | −0.0118 (17) | −0.0172 (19) |
C6D | 0.0239 (17) | 0.035 (2) | 0.028 (2) | −0.0005 (15) | −0.0039 (15) | −0.0127 (18) |
Cl6D | 0.0341 (5) | 0.0398 (6) | 0.0406 (6) | 0.0069 (4) | −0.0173 (4) | −0.0170 (5) |
N1E | 0.0273 (15) | 0.0307 (17) | 0.039 (2) | −0.0002 (13) | −0.0146 (15) | −0.0180 (16) |
C2E | 0.0204 (16) | 0.034 (2) | 0.041 (2) | 0.0047 (15) | −0.0158 (16) | −0.0199 (19) |
N2E | 0.0276 (16) | 0.039 (2) | 0.040 (2) | −0.0042 (14) | −0.0070 (15) | −0.0236 (18) |
C3E | 0.0242 (16) | 0.0275 (19) | 0.043 (3) | 0.0010 (14) | −0.0113 (16) | −0.0206 (18) |
C4E | 0.0248 (17) | 0.034 (2) | 0.048 (3) | 0.0004 (16) | −0.0125 (17) | −0.019 (2) |
C5E | 0.0295 (18) | 0.039 (2) | 0.034 (2) | 0.0063 (17) | −0.0116 (17) | −0.016 (2) |
C6E | 0.0329 (19) | 0.042 (2) | 0.040 (3) | 0.0065 (17) | −0.0160 (18) | −0.025 (2) |
N1A—C6A | 1.332 (4) | C4C—O4C | 1.247 (4) |
N1A—C2A | 1.349 (5) | C4C—C5C | 1.413 (5) |
C2A—N2A | 1.334 (5) | C5C—C6C | 1.351 (5) |
C2A—N3A | 1.352 (4) | C5C—H5C | 0.9500 |
N2A—H21A | 0.885 (19) | C6C—Cl6C | 1.733 (4) |
N2A—H22A | 0.880 (19) | N1D—C2D | 1.317 (5) |
N3A—C4A | 1.341 (5) | N1D—C6D | 1.340 (5) |
C4A—O4A | 1.303 (4) | C2D—N2D | 1.335 (5) |
C4A—C5A | 1.405 (5) | C2D—N3D | 1.356 (5) |
C5A—C6A | 1.356 (5) | N2D—H21D | 0.888 (19) |
C5A—H5A | 0.9500 | N2D—H22D | 0.870 (19) |
C6A—Cl6A | 1.740 (4) | N3D—C4D | 1.372 (5) |
N1B—C2B | 1.334 (5) | N3D—H3D | 0.891 (19) |
N1B—C6B | 1.342 (5) | C4D—O4D | 1.246 (4) |
C2B—N2B | 1.323 (5) | C4D—C5D | 1.412 (5) |
C2B—N3B | 1.369 (5) | C5D—C6D | 1.355 (5) |
N2B—H21B | 0.873 (19) | C5D—H5D | 0.9500 |
N2B—H22B | 0.897 (19) | C6D—Cl6D | 1.731 (4) |
N3B—C4B | 1.373 (5) | N1E—C6E | 1.338 (5) |
N3B—H3B | 0.875 (19) | N1E—C2E | 1.353 (4) |
C4B—O4B | 1.254 (4) | N1E—H1E | 0.890 (19) |
C4B—C5B | 1.417 (5) | C2E—N2E | 1.331 (5) |
C5B—C6B | 1.361 (5) | C2E—C3E | 1.400 (5) |
C5B—H5B | 0.9500 | N2E—H21E | 0.862 (19) |
C6B—Cl6B | 1.733 (4) | N2E—H22E | 0.889 (19) |
N1C—C2C | 1.326 (5) | C3E—C4E | 1.358 (6) |
N1C—C6C | 1.338 (5) | C3E—H3E | 0.9500 |
C2C—N2C | 1.338 (5) | C4E—C5E | 1.402 (5) |
C2C—N3C | 1.362 (4) | C4E—H4E | 0.9500 |
N2C—H21C | 0.880 (19) | C5E—C6E | 1.354 (6) |
N2C—H22C | 0.884 (19) | C5E—H5E | 0.9500 |
N3C—C4C | 1.389 (5) | C6E—H6E | 0.9500 |
N3C—H3C | 0.884 (19) | ||
C6A—N1A—C2A | 113.9 (3) | N3C—C4C—C5C | 114.7 (3) |
N2A—C2A—N1A | 116.6 (3) | C6C—C5C—C4C | 117.5 (3) |
N2A—C2A—N3A | 117.4 (3) | C6C—C5C—H5C | 121.2 |
N1A—C2A—N3A | 126.0 (3) | C4C—C5C—H5C | 121.2 |
C2A—N2A—H21A | 125 (3) | N1C—C6C—C5C | 127.5 (3) |
C2A—N2A—H22A | 111 (3) | N1C—C6C—Cl6C | 112.9 (3) |
H21A—N2A—H22A | 123 (4) | C5C—C6C—Cl6C | 119.6 (3) |
C4A—N3A—C2A | 117.3 (3) | C2D—N1D—C6D | 115.0 (3) |
O4A—C4A—N3A | 117.9 (3) | N1D—C2D—N2D | 119.7 (3) |
O4A—C4A—C5A | 121.4 (3) | N1D—C2D—N3D | 122.3 (3) |
N3A—C4A—C5A | 120.7 (3) | N2D—C2D—N3D | 117.9 (3) |
C6A—C5A—C4A | 116.1 (3) | C2D—N2D—H21D | 115 (3) |
C6A—C5A—H5A | 122.0 | C2D—N2D—H22D | 122 (3) |
C4A—C5A—H5A | 122.0 | H21D—N2D—H22D | 122 (4) |
N1A—C6A—C5A | 126.0 (3) | C2D—N3D—C4D | 123.5 (3) |
N1A—C6A—Cl6A | 114.4 (3) | C2D—N3D—H3D | 113 (3) |
C5A—C6A—Cl6A | 119.6 (3) | C4D—N3D—H3D | 123 (3) |
C2B—N1B—C6B | 115.0 (3) | O4D—C4D—N3D | 119.6 (3) |
N2B—C2B—N1B | 119.6 (3) | O4D—C4D—C5D | 125.7 (3) |
N2B—C2B—N3B | 118.1 (3) | N3D—C4D—C5D | 114.7 (3) |
N1B—C2B—N3B | 122.3 (3) | C6D—C5D—C4D | 117.4 (3) |
C2B—N2B—H21B | 113 (3) | C6D—C5D—H5D | 121.3 |
C2B—N2B—H22B | 122 (3) | C4D—C5D—H5D | 121.3 |
H21B—N2B—H22B | 125 (4) | N1D—C6D—C5D | 127.1 (3) |
C2B—N3B—C4B | 122.5 (3) | N1D—C6D—Cl6D | 113.8 (3) |
C2B—N3B—H3B | 116 (3) | C5D—C6D—Cl6D | 119.1 (3) |
C4B—N3B—H3B | 121 (3) | C6E—N1E—C2E | 121.7 (4) |
O4B—C4B—N3B | 119.1 (3) | C6E—N1E—H1E | 125 (3) |
O4B—C4B—C5B | 125.0 (3) | C2E—N1E—H1E | 114 (3) |
N3B—C4B—C5B | 115.8 (3) | N2E—C2E—N1E | 118.6 (4) |
C6B—C5B—C4B | 117.0 (3) | N2E—C2E—C3E | 123.2 (3) |
C6B—C5B—H5B | 121.5 | N1E—C2E—C3E | 118.3 (4) |
C4B—C5B—H5B | 121.5 | C2E—N2E—H21E | 117 (3) |
N1B—C6B—C5B | 127.2 (3) | C2E—N2E—H22E | 121 (3) |
N1B—C6B—Cl6B | 113.8 (3) | H21E—N2E—H22E | 118 (4) |
C5B—C6B—Cl6B | 119.0 (3) | C4E—C3E—C2E | 120.0 (3) |
C2C—N1C—C6C | 115.0 (3) | C4E—C3E—H3E | 120.0 |
N1C—C2C—N2C | 119.5 (3) | C2E—C3E—H3E | 120.0 |
N1C—C2C—N3C | 122.3 (3) | C3E—C4E—C5E | 120.0 (4) |
N2C—C2C—N3C | 118.2 (3) | C3E—C4E—H4E | 120.0 |
C2C—N2C—H21C | 112 (3) | C5E—C4E—H4E | 120.0 |
C2C—N2C—H22C | 118 (3) | C6E—C5E—C4E | 118.3 (4) |
H21C—N2C—H22C | 125 (4) | C6E—C5E—H5E | 120.9 |
C2C—N3C—C4C | 122.9 (3) | C4E—C5E—H5E | 120.9 |
C2C—N3C—H3C | 117 (3) | N1E—C6E—C5E | 121.6 (3) |
C4C—N3C—H3C | 120 (3) | N1E—C6E—H6E | 119.2 |
O4C—C4C—N3C | 118.1 (3) | C5E—C6E—H6E | 119.2 |
O4C—C4C—C5C | 127.1 (3) | ||
C6A—N1A—C2A—N2A | 179.9 (3) | C2C—N3C—C4C—O4C | −178.1 (3) |
C6A—N1A—C2A—N3A | 0.9 (5) | C2C—N3C—C4C—C5C | 1.4 (5) |
N2A—C2A—N3A—C4A | −178.0 (3) | O4C—C4C—C5C—C6C | 179.4 (4) |
N1A—C2A—N3A—C4A | 1.0 (5) | N3C—C4C—C5C—C6C | −0.1 (5) |
C2A—N3A—C4A—O4A | 177.2 (3) | C2C—N1C—C6C—C5C | 1.8 (5) |
C2A—N3A—C4A—C5A | −2.5 (5) | C2C—N1C—C6C—Cl6C | −178.2 (3) |
O4A—C4A—C5A—C6A | −177.7 (3) | C4C—C5C—C6C—N1C | −1.6 (6) |
N3A—C4A—C5A—C6A | 2.1 (5) | C4C—C5C—C6C—Cl6C | 178.5 (3) |
C2A—N1A—C6A—C5A | −1.4 (5) | C6D—N1D—C2D—N2D | −178.5 (3) |
C2A—N1A—C6A—Cl6A | 178.4 (3) | C6D—N1D—C2D—N3D | −0.7 (5) |
C4A—C5A—C6A—N1A | 0.0 (6) | N1D—C2D—N3D—C4D | 0.2 (6) |
C4A—C5A—C6A—Cl6A | −179.7 (3) | N2D—C2D—N3D—C4D | 178.1 (3) |
C6B—N1B—C2B—N2B | −179.9 (3) | C2D—N3D—C4D—O4D | −179.6 (4) |
C6B—N1B—C2B—N3B | 1.2 (5) | C2D—N3D—C4D—C5D | 0.8 (5) |
N2B—C2B—N3B—C4B | 177.0 (3) | O4D—C4D—C5D—C6D | 179.1 (4) |
N1B—C2B—N3B—C4B | −4.1 (5) | N3D—C4D—C5D—C6D | −1.4 (5) |
C2B—N3B—C4B—O4B | −175.6 (3) | C2D—N1D—C6D—C5D | 0.1 (6) |
C2B—N3B—C4B—C5B | 5.4 (5) | C2D—N1D—C6D—Cl6D | −179.6 (3) |
O4B—C4B—C5B—C6B | 177.0 (4) | C4D—C5D—C6D—N1D | 1.0 (6) |
N3B—C4B—C5B—C6B | −4.2 (5) | C4D—C5D—C6D—Cl6D | −179.3 (3) |
C2B—N1B—C6B—C5B | −0.2 (5) | C6E—N1E—C2E—N2E | −176.7 (3) |
C2B—N1B—C6B—Cl6B | −180.0 (3) | C6E—N1E—C2E—C3E | 3.2 (5) |
C4B—C5B—C6B—N1B | 1.8 (6) | N2E—C2E—C3E—C4E | 178.4 (3) |
C4B—C5B—C6B—Cl6B | −178.5 (3) | N1E—C2E—C3E—C4E | −1.5 (5) |
C6C—N1C—C2C—N2C | −178.3 (3) | C2E—C3E—C4E—C5E | −1.8 (5) |
C6C—N1C—C2C—N3C | −0.3 (5) | C3E—C4E—C5E—C6E | 3.6 (5) |
N1C—C2C—N3C—C4C | −1.3 (5) | C2E—N1E—C6E—C5E | −1.4 (5) |
N2C—C2C—N3C—C4C | 176.7 (3) | C4E—C5E—C6E—N1E | −2.0 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2A—H21A···O4B | 0.89 (2) | 2.08 (2) | 2.960 (4) | 173 (4) |
N2A—H22A···N1C | 0.88 (2) | 2.14 (2) | 3.014 (4) | 172 (4) |
N2B—H21B···N1D | 0.87 (2) | 2.14 (2) | 3.016 (4) | 178 (4) |
N2B—H22B···O4A | 0.90 (2) | 1.92 (2) | 2.820 (4) | 177 (4) |
N3B—H3B···N3A | 0.88 (2) | 2.03 (2) | 2.893 (4) | 167 (4) |
N2C—H21C···N1A | 0.88 (2) | 2.12 (2) | 2.999 (4) | 174 (4) |
N3C—H3C···O4Di | 0.88 (2) | 1.85 (2) | 2.730 (4) | 174 (4) |
N2D—H21D···N1B | 0.89 (2) | 2.06 (2) | 2.936 (4) | 171 (4) |
N3D—H3D···O4Cii | 0.89 (2) | 1.88 (2) | 2.760 (4) | 170 (4) |
N1E—H1E···O4A | 0.89 (2) | 1.70 (2) | 2.554 (4) | 160 (4) |
N2E—H21E···O4Biii | 0.86 (2) | 2.08 (2) | 2.905 (4) | 161 (4) |
N2E—H22E···O4Biv | 0.89 (2) | 2.26 (2) | 3.086 (4) | 155 (3) |
Symmetry codes: (i) x+1, y, z+1; (ii) x−1, y, z−1; (iii) x, y−1, z; (iv) −x+1, −y+1, −z+1. |
2C5H7N2+·2C4H3ClN3O−·10C4H4ClN3O·C5H6N2 | Z = 2 |
Mr = 2028.97 | F(000) = 2076 |
Triclinic, P1 | Dx = 1.628 Mg m−3 |
a = 14.0097 (7) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 14.0185 (7) Å | Cell parameters from 38798 reflections |
c = 21.4229 (11) Å | θ = 1.7–27.0° |
α = 83.774 (4)° | µ = 0.49 mm−1 |
β = 84.000 (4)° | T = 173 K |
γ = 83.554 (4)° | Needle, colourless |
V = 4137.9 (4) Å3 | 0.24 × 0.10 × 0.04 mm |
Stoe IPDSII two-circle diffractometer | 10620 reflections with I > 2σ(I) |
Radiation source: Genix 3D IµS microfocus X-ray source | Rint = 0.026 |
ω scans | θmax = 26.4°, θmin = 1.7° |
Absorption correction: multi-scan X-AREA (Stoe & Cie, 2001) | h = −17→17 |
Tmin = 0.890, Tmax = 0.980 | k = −17→17 |
20468 measured reflections | l = −26→26 |
16871 independent reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.136 | Hydrogen site location: mixed |
wR(F2) = 0.379 | H 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 parameters | Δρmax = 1.51 e Å−3 |
313 restraints | Δρmin = −1.23 e Å−3 |
2C5H7N2+·2C4H3ClN3O−·10C4H4ClN3O·C5H6N2 | γ = 83.554 (4)° |
Mr = 2028.97 | V = 4137.9 (4) Å3 |
Triclinic, P1 | Z = 2 |
a = 14.0097 (7) Å | Mo Kα radiation |
b = 14.0185 (7) Å | µ = 0.49 mm−1 |
c = 21.4229 (11) Å | T = 173 K |
α = 83.774 (4)° | 0.24 × 0.10 × 0.04 mm |
β = 84.000 (4)° |
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 = 0.980 | Rint = 0.026 |
20468 measured reflections |
R[F2 > 2σ(F2)] = 0.136 | 313 restraints |
wR(F2) = 0.379 | H 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 | Δρmax = 1.51 e Å−3 |
1350 parameters | Δρmin = −1.23 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
N1A | 0.8070 (6) | 0.1876 (6) | −0.0539 (4) | 0.0378 (19) | |
C2A | 0.8272 (7) | 0.1132 (7) | −0.0103 (4) | 0.032 (2) | |
N2A | 0.7919 (7) | 0.1203 (6) | 0.0490 (4) | 0.0377 (19) | |
H2A1 | 0.754 (6) | 0.171 (4) | 0.0612 (15) | 0.045* | |
H2A2 | 0.799 (7) | 0.073 (3) | 0.0790 (13) | 0.045* | |
N3A | 0.8834 (6) | 0.0318 (6) | −0.0253 (4) | 0.0340 (18) | |
H3A | 0.895 (8) | −0.015 (5) | 0.005 (3) | 0.041* | |
C4A | 0.9241 (7) | 0.0194 (6) | −0.0857 (5) | 0.033 (2) | |
O4A | 0.9772 (5) | −0.0576 (5) | −0.0950 (3) | 0.0390 (16) | |
C5A | 0.9006 (7) | 0.0955 (7) | −0.1325 (5) | 0.035 (2) | |
H5A | 0.9238 | 0.0922 | −0.1756 | 0.042* | |
C6A | 0.8433 (7) | 0.1735 (7) | −0.1128 (5) | 0.037 (2) | |
Cl6A | 0.8109 (2) | 0.26860 (18) | −0.16844 (12) | 0.0454 (6) | |
N1B | 0.9707 (6) | −0.2975 (6) | 0.0972 (4) | 0.0352 (18) | |
C2B | 0.9517 (7) | −0.2214 (6) | 0.0536 (4) | 0.0305 (19) | |
N2B | 0.9856 (7) | −0.2339 (6) | −0.0054 (4) | 0.039 (2) | |
H2B1 | 0.986 (8) | −0.187 (2) | −0.0359 (13) | 0.047* | |
H2B2 | 1.025 (6) | −0.284 (4) | −0.0158 (13) | 0.047* | |
N3B | 0.9001 (6) | −0.1365 (5) | 0.0659 (4) | 0.0316 (17) | |
C4B | 0.8655 (7) | −0.1254 (6) | 0.1247 (4) | 0.031 (2) | |
O4B | 0.8160 (6) | −0.0443 (5) | 0.1369 (3) | 0.0437 (18) | |
C5B | 0.8805 (7) | −0.2019 (7) | 0.1738 (5) | 0.037 (2) | |
H5B | 0.8552 | −0.1963 | 0.2163 | 0.045* | |
C6B | 0.9335 (8) | −0.2827 (7) | 0.1554 (5) | 0.037 (2) | |
Cl6B | 0.9569 (2) | −0.37946 (19) | 0.21292 (13) | 0.0484 (7) | |
N1C | 1.1026 (6) | −0.4340 (6) | −0.0268 (4) | 0.0387 (19) | |
C2C | 1.1197 (7) | −0.5009 (7) | 0.0211 (5) | 0.034 (2) | |
N2C | 1.0881 (7) | −0.4815 (6) | 0.0799 (4) | 0.042 (2) | |
H2C1 | 1.066 (8) | −0.4228 (19) | 0.0889 (15) | 0.050* | |
H2C2 | 1.097 (8) | −0.524 (3) | 0.1125 (9) | 0.050* | |
N3C | 1.1694 (6) | −0.5882 (6) | 0.0130 (4) | 0.0350 (18) | |
H3C | 1.176 (8) | −0.631 (6) | 0.046 (3) | 0.042* | |
C4C | 1.2057 (7) | −0.6156 (7) | −0.0468 (5) | 0.034 (2) | |
O4C | 1.2535 (5) | −0.6961 (5) | −0.0494 (3) | 0.0412 (17) | |
C5C | 1.1903 (8) | −0.5447 (7) | −0.0969 (5) | 0.040 (2) | |
H5C | 1.2158 | −0.5549 | −0.1388 | 0.048* | |
C6C | 1.1381 (7) | −0.4614 (7) | −0.0837 (5) | 0.037 (2) | |
Cl6C | 1.1113 (2) | −0.3749 (2) | −0.14599 (13) | 0.0496 (7) | |
N1D | 1.3220 (6) | −0.9898 (6) | 0.0840 (4) | 0.0349 (18) | |
C2D | 1.3019 (7) | −0.9198 (7) | 0.0384 (4) | 0.031 (2) | |
N2D | 1.3341 (7) | −0.9340 (6) | −0.0210 (4) | 0.039 (2) | |
H2D1 | 1.374 (6) | −0.985 (4) | −0.0304 (12) | 0.047* | |
H2D2 | 1.329 (8) | −0.888 (3) | −0.0521 (11) | 0.047* | |
N3D | 1.2528 (6) | −0.8345 (6) | 0.0508 (4) | 0.0343 (18) | |
H3D | 1.248 (8) | −0.794 (6) | 0.016 (3) | 0.041* | |
C4D | 1.2202 (7) | −0.8120 (7) | 0.1101 (5) | 0.033 (2) | |
O4D | 1.1777 (5) | −0.7284 (5) | 0.1189 (3) | 0.0394 (16) | |
C5D | 1.2398 (7) | −0.8858 (7) | 0.1605 (5) | 0.035 (2) | |
H5D | 1.2198 | −0.8766 | 0.2033 | 0.042* | |
C6D | 1.2881 (7) | −0.9685 (7) | 0.1433 (5) | 0.034 (2) | |
Cl6D | 1.3141 (2) | −1.06311 (19) | 0.20076 (12) | 0.0438 (6) | |
N1E | 1.4527 (6) | −1.1232 (6) | −0.0341 (4) | 0.0350 (18) | |
C2E | 1.4684 (7) | −1.1920 (6) | 0.0122 (5) | 0.033 (2) | |
N2E | 1.4337 (7) | −1.1762 (6) | 0.0710 (4) | 0.040 (2) | |
H2E1 | 1.401 (7) | −1.121 (3) | 0.0802 (14) | 0.048* | |
H2E2 | 1.444 (7) | −1.219 (4) | 0.1033 (10) | 0.048* | |
N3E | 1.5202 (6) | −1.2778 (6) | 0.0022 (4) | 0.0351 (18) | |
H3E | 1.535 (8) | −1.322 (6) | 0.033 (3) | 0.042* | |
C4E | 1.5597 (8) | −1.3009 (8) | −0.0572 (5) | 0.041 (2) | |
O4E | 1.6042 (6) | −1.3822 (5) | −0.0611 (3) | 0.0418 (17) | |
C5E | 1.5442 (7) | −1.2283 (7) | −0.1069 (5) | 0.035 (2) | |
H5E | 1.5695 | −1.2373 | −0.1490 | 0.041* | |
C6E | 1.4910 (7) | −1.1439 (7) | −0.0922 (5) | 0.035 (2) | |
Cl6E | 1.4673 (2) | −1.05247 (18) | −0.15099 (12) | 0.0427 (6) | |
N1F | 1.6781 (6) | −1.6819 (5) | 0.0737 (4) | 0.0342 (18) | |
C2F | 1.6636 (7) | −1.6118 (7) | 0.0267 (4) | 0.032 (2) | |
N2F | 1.6951 (7) | −1.6277 (6) | −0.0318 (4) | 0.039 (2) | |
H2F1 | 1.732 (7) | −1.680 (4) | −0.0420 (13) | 0.047* | |
H2F2 | 1.691 (8) | −1.584 (3) | −0.0642 (10) | 0.047* | |
N3F | 1.6143 (6) | −1.5252 (5) | 0.0380 (4) | 0.0341 (18) | |
H3F | 1.600 (8) | −1.479 (5) | 0.008 (3) | 0.041* | |
C4F | 1.5750 (8) | −1.5011 (7) | 0.0963 (5) | 0.037 (2) | |
O4F | 1.5300 (6) | −1.4199 (5) | 0.1026 (3) | 0.0426 (17) | |
C5F | 1.5915 (8) | −1.5741 (7) | 0.1467 (5) | 0.038 (2) | |
H5F | 1.5676 | −1.5643 | 0.1889 | 0.046* | |
C6F | 1.6431 (7) | −1.6594 (7) | 0.1320 (5) | 0.034 (2) | |
Cl6F | 1.6654 (2) | −1.74992 (19) | 0.19134 (13) | 0.0469 (7) | |
N1G | 0.8200 (6) | −0.0350 (5) | 0.5557 (4) | 0.0309 (17) | |
C2G | 0.7576 (7) | 0.0008 (7) | 0.5119 (5) | 0.034 (2) | |
N2G | 0.7896 (6) | −0.0102 (7) | 0.4517 (4) | 0.039 (2) | |
H2G1 | 0.7494 (18) | −0.007 (8) | 0.4224 (12) | 0.047* | |
H2G2 | 0.841 (5) | −0.050 (6) | 0.4418 (12) | 0.047* | |
N3G | 0.6706 (6) | 0.0473 (5) | 0.5244 (4) | 0.0331 (17) | |
C4G | 0.6411 (7) | 0.0639 (7) | 0.5845 (5) | 0.035 (2) | |
O4G | 0.5587 (5) | 0.1121 (5) | 0.5965 (3) | 0.0362 (15) | |
C5G | 0.6991 (7) | 0.0262 (7) | 0.6329 (5) | 0.033 (2) | |
H5G | 0.6792 | 0.0344 | 0.6760 | 0.040* | |
C6G | 0.7854 (7) | −0.0226 (7) | 0.6148 (4) | 0.031 (2) | |
Cl6G | 0.86379 (18) | −0.07143 (19) | 0.67053 (12) | 0.0410 (6) | |
N1H | 0.3919 (6) | 0.1808 (6) | 0.4014 (4) | 0.0342 (18) | |
C2H | 0.4505 (7) | 0.1451 (7) | 0.4446 (5) | 0.034 (2) | |
N2H | 0.4239 (6) | 0.1598 (6) | 0.5048 (4) | 0.0356 (18) | |
H2H1 | 0.366 (3) | 0.188 (7) | 0.5168 (14) | 0.043* | |
H2H2 | 0.465 (3) | 0.149 (8) | 0.5339 (13) | 0.043* | |
N3H | 0.5380 (6) | 0.0979 (6) | 0.4298 (4) | 0.0318 (17) | |
H3H | 0.572 (6) | 0.078 (7) | 0.462 (3) | 0.038* | |
C4H | 0.5718 (6) | 0.0785 (6) | 0.3694 (4) | 0.0283 (19) | |
O4H | 0.6520 (5) | 0.0335 (5) | 0.3583 (3) | 0.0388 (16) | |
C5H | 0.5104 (7) | 0.1178 (7) | 0.3216 (4) | 0.035 (2) | |
H5H | 0.5288 | 0.1114 | 0.2782 | 0.042* | |
C6H | 0.4243 (7) | 0.1648 (7) | 0.3416 (5) | 0.033 (2) | |
Cl6H | 0.34671 (19) | 0.2150 (2) | 0.28590 (12) | 0.0427 (6) | |
N1I | 0.2221 (6) | 0.2633 (6) | 0.5268 (4) | 0.0343 (18) | |
C2I | 0.1672 (7) | 0.2957 (7) | 0.4789 (5) | 0.035 (2) | |
N2I | 0.2013 (7) | 0.2836 (7) | 0.4204 (4) | 0.045 (2) | |
H2I1 | 0.261 (2) | 0.261 (8) | 0.4093 (14) | 0.054* | |
H2I2 | 0.169 (4) | 0.302 (8) | 0.3873 (9) | 0.054* | |
N3I | 0.0780 (6) | 0.3425 (6) | 0.4907 (4) | 0.0334 (18) | |
H3I | 0.040 (6) | 0.359 (8) | 0.461 (3) | 0.040* | |
C4I | 0.0360 (7) | 0.3598 (7) | 0.5500 (5) | 0.036 (2) | |
O4I | −0.0476 (5) | 0.4035 (5) | 0.5554 (3) | 0.0427 (17) | |
C5I | 0.0929 (7) | 0.3276 (7) | 0.6002 (5) | 0.035 (2) | |
H5I | 0.0710 | 0.3379 | 0.6426 | 0.042* | |
C6I | 0.1812 (7) | 0.2810 (7) | 0.5841 (5) | 0.036 (2) | |
Cl6I | 0.2543 (2) | 0.2356 (2) | 0.64367 (13) | 0.0458 (6) | |
N1K | −0.3005 (6) | 0.5248 (5) | 0.4172 (4) | 0.0321 (17) | |
C2K | −0.2457 (7) | 0.4941 (7) | 0.4638 (5) | 0.035 (2) | |
N2K | −0.2809 (6) | 0.5090 (6) | 0.5233 (4) | 0.0383 (19) | |
H2K1 | −0.342 (2) | 0.529 (8) | 0.5321 (15) | 0.046* | |
H2K2 | −0.245 (3) | 0.493 (8) | 0.5549 (10) | 0.046* | |
N3K | −0.1567 (6) | 0.4474 (6) | 0.4541 (4) | 0.0320 (17) | |
H3K | −0.121 (6) | 0.436 (8) | 0.486 (3) | 0.038* | |
C4K | −0.1135 (7) | 0.4307 (7) | 0.3947 (5) | 0.035 (2) | |
O4K | −0.0316 (5) | 0.3869 (5) | 0.3894 (3) | 0.0421 (17) | |
C5K | −0.1707 (8) | 0.4642 (7) | 0.3446 (5) | 0.037 (2) | |
H5K | −0.1477 | 0.4559 | 0.3021 | 0.044* | |
C6K | −0.2584 (8) | 0.5082 (7) | 0.3598 (5) | 0.037 (2) | |
Cl6K | −0.3318 (2) | 0.5513 (2) | 0.29917 (13) | 0.0462 (6) | |
N1L | −0.4776 (6) | 0.6115 (6) | 0.5423 (4) | 0.0345 (18) | |
C2L | −0.5317 (7) | 0.6457 (6) | 0.4955 (5) | 0.033 (2) | |
N2L | −0.4968 (6) | 0.6328 (7) | 0.4369 (4) | 0.041 (2) | |
H2L1 | −0.445 (5) | 0.593 (6) | 0.4272 (12) | 0.049* | |
H2L2 | −0.532 (2) | 0.641 (8) | 0.4049 (11) | 0.049* | |
N3L | −0.6201 (6) | 0.6923 (6) | 0.5061 (4) | 0.0335 (18) | |
H3L | −0.656 (8) | 0.710 (8) | 0.482 (5) | 0.040* | |
C4L | −0.6646 (7) | 0.7103 (6) | 0.5665 (4) | 0.0281 (19) | |
O4L | −0.7475 (5) | 0.7521 (5) | 0.5710 (3) | 0.0386 (16) | |
C5L | −0.6064 (7) | 0.6761 (7) | 0.6159 (5) | 0.034 (2) | |
H5L | −0.6286 | 0.6864 | 0.6583 | 0.040* | |
C6L | −0.5184 (7) | 0.6286 (7) | 0.6018 (5) | 0.032 (2) | |
Cl6L | −0.4470 (2) | 0.5796 (2) | 0.66006 (13) | 0.0448 (6) | |
N1M | −1.0047 (6) | 0.8800 (6) | 0.4321 (4) | 0.0354 (18) | |
C2M | −0.9486 (7) | 0.8539 (6) | 0.4784 (5) | 0.031 (2) | |
N2M | −0.9815 (6) | 0.8748 (7) | 0.5375 (4) | 0.040 (2) | |
H2M1 | −1.040 (3) | 0.904 (7) | 0.5450 (15) | 0.048* | |
H2M2 | −0.946 (4) | 0.857 (7) | 0.5689 (11) | 0.048* | |
N3M | −0.8590 (6) | 0.8073 (6) | 0.4699 (4) | 0.0318 (17) | |
H3M | −0.822 (8) | 0.785 (8) | 0.505 (5) | 0.038* | |
C4M | −0.8184 (7) | 0.7827 (7) | 0.4117 (4) | 0.031 (2) | |
O4M | −0.7358 (5) | 0.7379 (5) | 0.4070 (3) | 0.0389 (16) | |
C5M | −0.8756 (7) | 0.8111 (8) | 0.3600 (5) | 0.038 (2) | |
H5M | −0.8533 | 0.7992 | 0.3179 | 0.046* | |
C6M | −0.9635 (7) | 0.8559 (7) | 0.3756 (5) | 0.035 (2) | |
Cl6M | −1.0380 (2) | 0.8939 (2) | 0.31489 (12) | 0.0435 (6) | |
N1O | −0.4965 (6) | 0.8227 (6) | 0.2960 (4) | 0.0344 (18) | |
H1O | −0.528 (8) | 0.850 (8) | 0.334 (5) | 0.041* | |
C3O | −0.4774 (8) | 0.7158 (7) | 0.2161 (5) | 0.037 (2) | |
H3O | −0.4972 | 0.6623 | 0.1989 | 0.045* | |
C6O | −0.4212 (7) | 0.8666 (7) | 0.2681 (5) | 0.038 (2) | |
H6O | −0.4008 | 0.9185 | 0.2867 | 0.045* | |
C2O | −0.5275 (7) | 0.7503 (7) | 0.2715 (4) | 0.031 (2) | |
N2O | −0.6046 (7) | 0.7081 (7) | 0.3007 (5) | 0.048 (2) | |
H2O1 | −0.636 (5) | 0.730 (6) | 0.335 (3) | 0.058* | |
H2O2 | −0.608 (5) | 0.646 (2) | 0.299 (5) | 0.058* | |
C4O | −0.4012 (7) | 0.7601 (7) | 0.1882 (5) | 0.038 (2) | |
H4O | −0.3671 | 0.7373 | 0.1511 | 0.045* | |
C5O | −0.3720 (7) | 0.8377 (8) | 0.2124 (5) | 0.041 (2) | |
H5O | −0.3199 | 0.8705 | 0.1919 | 0.049* | |
N1P | 0.9210 (6) | 0.1114 (5) | 0.2057 (3) | 0.0333 (18) | |
H1P | 0.931 (4) | 0.079 (5) | 0.172 (2) | 0.040* | |
C2P | 0.8464 (7) | 0.0993 (6) | 0.2538 (4) | 0.031 (2) | |
N2P | 0.7876 (7) | 0.0364 (7) | 0.2480 (4) | 0.040 (2) | |
H2P1 | 0.794 (4) | −0.004 (5) | 0.219 (3) | 0.048* | |
H2P2 | 0.730 (3) | 0.032 (5) | 0.269 (4) | 0.048* | |
C6P | 0.9861 (8) | 0.1762 (8) | 0.2108 (5) | 0.045 (3) | |
H6P | 1.0370 | 0.1825 | 0.1781 | 0.054* | |
C5P | 0.9827 (9) | 0.2299 (9) | 0.2579 (6) | 0.050 (3) | |
H5P | 1.0291 | 0.2737 | 0.2598 | 0.060* | |
C4P | 0.9059 (8) | 0.2184 (7) | 0.3052 (5) | 0.038 (2) | |
H4P | 0.9000 | 0.2572 | 0.3394 | 0.045* | |
C3P | 0.8420 (7) | 0.1566 (7) | 0.3043 (4) | 0.033 (2) | |
H3P | 0.7925 | 0.1506 | 0.3380 | 0.040* | |
N1R | 1.7088 (7) | −1.5563 (6) | −0.2592 (4) | 0.0416 (18) | |
C2R | 1.7214 (16) | −1.4963 (15) | −0.2174 (11) | 0.041 (5) | 0.522 (16) |
N2R | 1.6537 (14) | −1.5003 (11) | −0.1663 (9) | 0.046 (4) | 0.522 (16) |
H2R1 | 1.618 (9) | −1.549 (7) | −0.161 (5) | 0.055* | 0.522 (16) |
H2R2 | 1.639 (11) | −1.449 (5) | −0.146 (6) | 0.055* | 0.522 (16) |
C3R | 1.788 (2) | −1.431 (2) | −0.2198 (17) | 0.042 (5) | 0.522 (16) |
H3R | 1.7866 | −1.3863 | −0.1892 | 0.050* | 0.522 (16) |
C4R | 1.857 (2) | −1.435 (2) | −0.2704 (14) | 0.045 (5) | 0.522 (16) |
H4R | 1.9066 | −1.3934 | −0.2753 | 0.054* | 0.522 (16) |
C5R | 1.8550 (15) | −1.5039 (14) | −0.3160 (10) | 0.038 (4) | 0.522 (16) |
H5R | 1.9021 | −1.5103 | −0.3509 | 0.045* | 0.522 (16) |
C6R | 1.7826 (18) | −1.5560 (19) | −0.3048 (12) | 0.038 (4) | 0.522 (16) |
H6R | 1.7816 | −1.6020 | −0.3342 | 0.046* | 0.522 (16) |
C2S | 1.783 (2) | −1.5204 (19) | −0.2933 (12) | 0.035 (4) | 0.478 (16) |
N2S | 1.8026 (13) | −1.5677 (13) | −0.3489 (10) | 0.043 (5) | 0.478 (16) |
H2S1 | 1.8644 (18) | −1.582 (15) | −0.360 (6) | 0.051* | 0.478 (16) |
H2S2 | 1.757 (6) | −1.601 (11) | −0.357 (5) | 0.051* | 0.478 (16) |
C3S | 1.840 (2) | −1.4626 (19) | −0.2806 (14) | 0.034 (4) | 0.478 (16) |
H3S | 1.8972 | −1.4513 | −0.3065 | 0.041* | 0.478 (16) |
C4S | 1.813 (2) | −1.418 (3) | −0.2278 (17) | 0.039 (6) | 0.478 (16) |
H4S | 1.8514 | −1.3721 | −0.2171 | 0.046* | 0.478 (16) |
C5S | 1.7279 (16) | −1.4377 (14) | −0.1872 (10) | 0.036 (4) | 0.478 (16) |
H5S | 1.7065 | −1.4069 | −0.1501 | 0.044* | 0.478 (16) |
C6S | 1.684 (2) | −1.5034 (18) | −0.2079 (13) | 0.037 (5) | 0.478 (16) |
H6S | 1.6258 | −1.5175 | −0.1838 | 0.044* | 0.478 (16) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1A | 0.040 (5) | 0.035 (4) | 0.038 (5) | 0.001 (4) | −0.003 (4) | −0.003 (4) |
C2A | 0.032 (5) | 0.029 (5) | 0.034 (5) | 0.001 (4) | −0.003 (4) | −0.002 (4) |
N2A | 0.042 (5) | 0.033 (4) | 0.036 (4) | 0.001 (4) | −0.002 (4) | −0.002 (3) |
N3A | 0.034 (4) | 0.028 (4) | 0.039 (5) | −0.001 (3) | −0.002 (4) | −0.004 (3) |
C4A | 0.036 (5) | 0.024 (4) | 0.039 (5) | 0.001 (4) | −0.005 (4) | 0.000 (4) |
O4A | 0.044 (4) | 0.032 (4) | 0.039 (4) | 0.005 (3) | −0.001 (3) | −0.004 (3) |
C5A | 0.043 (6) | 0.032 (5) | 0.029 (5) | −0.003 (4) | −0.003 (4) | 0.002 (4) |
C6A | 0.035 (5) | 0.035 (5) | 0.039 (5) | −0.002 (4) | −0.001 (4) | −0.002 (4) |
Cl6A | 0.0614 (17) | 0.0336 (13) | 0.0381 (13) | 0.0053 (11) | −0.0092 (12) | 0.0035 (10) |
N1B | 0.042 (5) | 0.025 (4) | 0.039 (4) | 0.000 (3) | −0.005 (4) | −0.004 (3) |
C2B | 0.032 (5) | 0.026 (4) | 0.034 (5) | −0.003 (4) | −0.004 (4) | −0.004 (4) |
N2B | 0.051 (5) | 0.024 (4) | 0.038 (5) | 0.011 (4) | 0.001 (4) | −0.004 (3) |
N3B | 0.033 (4) | 0.024 (4) | 0.037 (4) | 0.003 (3) | −0.006 (3) | −0.007 (3) |
C4B | 0.037 (5) | 0.026 (4) | 0.030 (5) | −0.007 (4) | −0.001 (4) | −0.005 (4) |
O4B | 0.060 (5) | 0.032 (4) | 0.035 (4) | 0.007 (3) | 0.001 (3) | −0.005 (3) |
C5B | 0.042 (6) | 0.035 (5) | 0.033 (5) | 0.000 (4) | 0.000 (4) | 0.002 (4) |
C6B | 0.041 (6) | 0.033 (5) | 0.036 (5) | −0.005 (4) | 0.000 (4) | −0.001 (4) |
Cl6B | 0.0613 (18) | 0.0395 (14) | 0.0401 (14) | 0.0027 (12) | −0.0058 (12) | 0.0081 (11) |
N1C | 0.040 (5) | 0.027 (4) | 0.047 (5) | 0.005 (3) | −0.004 (4) | −0.005 (3) |
C2C | 0.029 (5) | 0.030 (5) | 0.041 (5) | 0.000 (4) | −0.003 (4) | −0.002 (4) |
N2C | 0.062 (6) | 0.028 (4) | 0.032 (4) | 0.008 (4) | −0.003 (4) | 0.002 (3) |
N3C | 0.040 (5) | 0.028 (4) | 0.037 (4) | 0.002 (3) | −0.003 (4) | −0.006 (3) |
C4C | 0.029 (5) | 0.027 (5) | 0.046 (6) | −0.010 (4) | 0.003 (4) | 0.001 (4) |
O4C | 0.049 (4) | 0.031 (4) | 0.041 (4) | 0.005 (3) | −0.006 (3) | −0.003 (3) |
C5C | 0.042 (6) | 0.037 (5) | 0.041 (6) | −0.006 (4) | −0.008 (5) | −0.001 (4) |
C6C | 0.036 (5) | 0.034 (5) | 0.042 (6) | −0.007 (4) | −0.006 (4) | −0.002 (4) |
Cl6C | 0.0613 (18) | 0.0417 (14) | 0.0432 (14) | −0.0007 (12) | −0.0101 (13) | 0.0084 (11) |
N1D | 0.040 (5) | 0.031 (4) | 0.034 (4) | 0.002 (3) | −0.007 (4) | −0.004 (3) |
C2D | 0.030 (5) | 0.033 (5) | 0.033 (5) | −0.008 (4) | −0.004 (4) | −0.005 (4) |
N2D | 0.052 (6) | 0.034 (5) | 0.029 (4) | 0.008 (4) | −0.002 (4) | −0.001 (3) |
N3D | 0.044 (5) | 0.026 (4) | 0.031 (4) | 0.001 (3) | −0.004 (4) | 0.001 (3) |
C4D | 0.032 (5) | 0.030 (5) | 0.037 (5) | −0.003 (4) | −0.003 (4) | −0.003 (4) |
O4D | 0.049 (4) | 0.027 (3) | 0.042 (4) | 0.002 (3) | −0.007 (3) | −0.009 (3) |
C5D | 0.036 (5) | 0.036 (5) | 0.035 (5) | 0.000 (4) | −0.011 (4) | −0.001 (4) |
C6D | 0.034 (5) | 0.037 (5) | 0.033 (5) | −0.008 (4) | −0.001 (4) | 0.000 (4) |
Cl6D | 0.0604 (17) | 0.0384 (13) | 0.0305 (12) | 0.0029 (12) | −0.0086 (11) | 0.0018 (10) |
N1E | 0.044 (5) | 0.029 (4) | 0.030 (4) | 0.001 (3) | −0.005 (4) | 0.001 (3) |
C2E | 0.038 (5) | 0.021 (4) | 0.038 (5) | −0.002 (4) | −0.005 (4) | 0.000 (4) |
N2E | 0.053 (6) | 0.031 (4) | 0.033 (4) | 0.011 (4) | −0.008 (4) | 0.000 (3) |
N3E | 0.042 (5) | 0.029 (4) | 0.033 (4) | 0.002 (3) | −0.001 (4) | −0.004 (3) |
C4E | 0.035 (5) | 0.036 (5) | 0.050 (6) | −0.001 (4) | −0.008 (5) | 0.005 (5) |
O4E | 0.052 (5) | 0.035 (4) | 0.035 (4) | 0.013 (3) | −0.004 (3) | −0.006 (3) |
C5E | 0.037 (5) | 0.028 (5) | 0.035 (5) | 0.002 (4) | 0.000 (4) | 0.001 (4) |
C6E | 0.034 (5) | 0.036 (5) | 0.034 (5) | −0.002 (4) | −0.009 (4) | 0.002 (4) |
Cl6E | 0.0557 (16) | 0.0359 (13) | 0.0351 (12) | 0.0012 (11) | −0.0106 (11) | 0.0025 (10) |
N1F | 0.043 (5) | 0.022 (4) | 0.036 (4) | 0.003 (3) | −0.005 (4) | 0.003 (3) |
C2F | 0.034 (5) | 0.027 (5) | 0.035 (5) | 0.001 (4) | −0.004 (4) | −0.006 (4) |
N2F | 0.047 (5) | 0.029 (4) | 0.039 (5) | 0.011 (4) | −0.003 (4) | −0.002 (3) |
N3F | 0.037 (5) | 0.022 (4) | 0.039 (4) | 0.009 (3) | 0.001 (4) | −0.002 (3) |
C4F | 0.043 (6) | 0.026 (5) | 0.039 (5) | 0.006 (4) | −0.004 (4) | 0.004 (4) |
O4F | 0.056 (5) | 0.030 (4) | 0.039 (4) | 0.003 (3) | 0.004 (3) | −0.006 (3) |
C5F | 0.044 (6) | 0.041 (6) | 0.029 (5) | −0.004 (4) | −0.003 (4) | 0.001 (4) |
C6F | 0.033 (5) | 0.028 (5) | 0.041 (5) | −0.001 (4) | −0.007 (4) | 0.003 (4) |
Cl6F | 0.0528 (16) | 0.0386 (13) | 0.0463 (14) | 0.0010 (11) | −0.0107 (12) | 0.0090 (11) |
N1G | 0.031 (4) | 0.028 (4) | 0.032 (4) | 0.003 (3) | 0.000 (3) | −0.005 (3) |
C2G | 0.029 (5) | 0.038 (5) | 0.035 (5) | −0.004 (4) | −0.003 (4) | 0.000 (4) |
N2G | 0.034 (5) | 0.050 (5) | 0.031 (4) | 0.009 (4) | −0.005 (4) | −0.003 (4) |
N3G | 0.038 (5) | 0.024 (4) | 0.038 (4) | −0.003 (3) | −0.008 (4) | −0.004 (3) |
C4G | 0.027 (5) | 0.044 (6) | 0.035 (5) | −0.004 (4) | −0.003 (4) | −0.003 (4) |
O4G | 0.030 (4) | 0.040 (4) | 0.037 (4) | 0.005 (3) | −0.001 (3) | −0.007 (3) |
C5G | 0.026 (5) | 0.039 (5) | 0.032 (5) | 0.000 (4) | 0.000 (4) | −0.005 (4) |
C6G | 0.027 (5) | 0.030 (5) | 0.034 (5) | 0.000 (4) | −0.001 (4) | 0.003 (4) |
Cl6G | 0.0363 (13) | 0.0479 (14) | 0.0358 (12) | 0.0048 (10) | −0.0054 (10) | 0.0021 (10) |
N1H | 0.036 (4) | 0.033 (4) | 0.034 (4) | 0.001 (3) | −0.008 (3) | −0.004 (3) |
C2H | 0.034 (5) | 0.031 (5) | 0.037 (5) | 0.002 (4) | 0.001 (4) | −0.007 (4) |
N2H | 0.028 (4) | 0.043 (5) | 0.034 (4) | 0.003 (4) | 0.003 (3) | −0.008 (4) |
N3H | 0.028 (4) | 0.029 (4) | 0.037 (4) | 0.004 (3) | −0.007 (3) | −0.004 (3) |
C4H | 0.027 (5) | 0.029 (4) | 0.029 (4) | −0.001 (4) | −0.002 (4) | −0.007 (4) |
O4H | 0.034 (4) | 0.046 (4) | 0.037 (4) | 0.003 (3) | −0.005 (3) | −0.013 (3) |
C5H | 0.042 (6) | 0.034 (5) | 0.027 (5) | −0.001 (4) | −0.002 (4) | −0.004 (4) |
C6H | 0.034 (5) | 0.033 (5) | 0.033 (5) | −0.001 (4) | −0.001 (4) | −0.004 (4) |
Cl6H | 0.0392 (14) | 0.0522 (15) | 0.0357 (13) | 0.0039 (11) | −0.0110 (10) | −0.0020 (11) |
N1I | 0.032 (4) | 0.032 (4) | 0.038 (4) | 0.000 (3) | −0.008 (3) | 0.001 (3) |
C2I | 0.032 (5) | 0.033 (5) | 0.041 (5) | −0.001 (4) | −0.008 (4) | −0.003 (4) |
N2I | 0.045 (5) | 0.047 (5) | 0.038 (5) | 0.012 (4) | −0.001 (4) | −0.006 (4) |
N3I | 0.033 (4) | 0.030 (4) | 0.037 (4) | 0.002 (3) | −0.009 (3) | −0.001 (3) |
C4I | 0.033 (5) | 0.030 (5) | 0.046 (6) | −0.009 (4) | −0.001 (4) | −0.005 (4) |
O4I | 0.034 (4) | 0.050 (4) | 0.043 (4) | 0.006 (3) | −0.004 (3) | −0.007 (3) |
C5I | 0.039 (6) | 0.037 (5) | 0.030 (5) | −0.006 (4) | −0.002 (4) | −0.006 (4) |
C6I | 0.038 (5) | 0.033 (5) | 0.036 (5) | −0.001 (4) | −0.009 (4) | 0.004 (4) |
Cl6I | 0.0439 (15) | 0.0499 (15) | 0.0431 (14) | −0.0035 (12) | −0.0136 (12) | 0.0063 (11) |
N1K | 0.035 (4) | 0.027 (4) | 0.032 (4) | 0.003 (3) | −0.003 (3) | 0.000 (3) |
C2K | 0.038 (5) | 0.029 (5) | 0.037 (5) | −0.007 (4) | −0.005 (4) | 0.002 (4) |
N2K | 0.036 (5) | 0.041 (5) | 0.037 (5) | 0.000 (4) | −0.004 (4) | 0.001 (4) |
N3K | 0.030 (4) | 0.037 (4) | 0.027 (4) | 0.000 (3) | −0.004 (3) | 0.000 (3) |
C4K | 0.031 (5) | 0.027 (5) | 0.044 (6) | 0.004 (4) | −0.006 (4) | 0.003 (4) |
O4K | 0.036 (4) | 0.047 (4) | 0.042 (4) | 0.005 (3) | −0.004 (3) | −0.007 (3) |
C5K | 0.044 (6) | 0.036 (5) | 0.031 (5) | −0.004 (4) | −0.001 (4) | −0.005 (4) |
C6K | 0.043 (6) | 0.029 (5) | 0.038 (5) | −0.002 (4) | −0.013 (4) | 0.002 (4) |
Cl6K | 0.0470 (15) | 0.0502 (15) | 0.0401 (14) | 0.0031 (12) | −0.0149 (12) | 0.0029 (11) |
N1L | 0.031 (4) | 0.035 (4) | 0.036 (4) | 0.005 (3) | −0.009 (3) | 0.000 (3) |
C2L | 0.030 (5) | 0.027 (5) | 0.041 (5) | 0.003 (4) | −0.003 (4) | −0.008 (4) |
N2L | 0.038 (5) | 0.045 (5) | 0.037 (5) | 0.006 (4) | −0.001 (4) | −0.008 (4) |
N3L | 0.027 (4) | 0.036 (4) | 0.036 (4) | 0.008 (3) | −0.003 (3) | −0.007 (3) |
C4L | 0.031 (5) | 0.020 (4) | 0.032 (5) | 0.000 (3) | −0.002 (4) | −0.002 (3) |
O4L | 0.035 (4) | 0.039 (4) | 0.041 (4) | 0.010 (3) | −0.005 (3) | −0.008 (3) |
C5L | 0.038 (5) | 0.030 (5) | 0.033 (5) | −0.005 (4) | −0.008 (4) | 0.003 (4) |
C6L | 0.026 (5) | 0.035 (5) | 0.035 (5) | 0.000 (4) | −0.005 (4) | −0.003 (4) |
Cl6L | 0.0429 (14) | 0.0500 (15) | 0.0403 (13) | 0.0030 (11) | −0.0133 (11) | 0.0018 (11) |
N1M | 0.039 (5) | 0.033 (4) | 0.035 (4) | −0.004 (3) | −0.002 (4) | −0.010 (3) |
C2M | 0.027 (5) | 0.027 (4) | 0.039 (5) | 0.000 (4) | 0.001 (4) | −0.006 (4) |
N2M | 0.039 (5) | 0.050 (5) | 0.029 (4) | 0.008 (4) | 0.002 (4) | −0.015 (4) |
N3M | 0.031 (4) | 0.029 (4) | 0.035 (4) | 0.001 (3) | 0.001 (3) | −0.011 (3) |
C4M | 0.034 (5) | 0.032 (5) | 0.028 (5) | −0.006 (4) | 0.002 (4) | −0.010 (4) |
O4M | 0.031 (4) | 0.045 (4) | 0.037 (4) | 0.006 (3) | 0.001 (3) | −0.007 (3) |
C5M | 0.037 (5) | 0.044 (6) | 0.033 (5) | −0.006 (4) | −0.002 (4) | −0.006 (4) |
C6M | 0.034 (5) | 0.035 (5) | 0.037 (5) | −0.006 (4) | −0.002 (4) | −0.009 (4) |
Cl6M | 0.0428 (14) | 0.0506 (15) | 0.0377 (13) | −0.0031 (11) | −0.0125 (11) | −0.0001 (11) |
N1O | 0.036 (5) | 0.033 (4) | 0.031 (4) | 0.002 (3) | 0.001 (4) | 0.001 (3) |
C3O | 0.046 (6) | 0.034 (5) | 0.033 (5) | −0.005 (4) | −0.007 (4) | −0.007 (4) |
C6O | 0.038 (6) | 0.029 (5) | 0.050 (6) | −0.009 (4) | −0.014 (5) | −0.009 (4) |
C2O | 0.034 (5) | 0.030 (5) | 0.030 (5) | −0.005 (4) | −0.009 (4) | 0.005 (4) |
N2O | 0.046 (6) | 0.048 (6) | 0.055 (6) | −0.016 (4) | 0.006 (5) | −0.017 (5) |
C4O | 0.035 (5) | 0.040 (5) | 0.033 (5) | 0.005 (4) | 0.005 (4) | 0.001 (4) |
C5O | 0.031 (5) | 0.050 (6) | 0.036 (5) | 0.005 (4) | 0.003 (4) | 0.006 (5) |
N1P | 0.039 (5) | 0.033 (4) | 0.025 (4) | 0.002 (3) | 0.001 (3) | 0.000 (3) |
C2P | 0.042 (6) | 0.027 (5) | 0.023 (4) | 0.000 (4) | −0.004 (4) | −0.001 (3) |
N2P | 0.042 (5) | 0.042 (5) | 0.037 (5) | −0.004 (4) | −0.002 (4) | −0.009 (4) |
C6P | 0.035 (6) | 0.051 (7) | 0.043 (6) | 0.000 (5) | −0.002 (5) | 0.015 (5) |
C5P | 0.046 (7) | 0.046 (6) | 0.058 (7) | −0.012 (5) | −0.011 (6) | 0.010 (5) |
C4P | 0.050 (6) | 0.029 (5) | 0.036 (5) | 0.000 (4) | −0.015 (5) | −0.005 (4) |
C3P | 0.034 (5) | 0.039 (5) | 0.026 (4) | 0.003 (4) | −0.005 (4) | −0.008 (4) |
N1R | 0.047 (5) | 0.036 (4) | 0.043 (4) | −0.005 (4) | −0.008 (3) | −0.008 (3) |
C2R | 0.046 (11) | 0.043 (10) | 0.034 (9) | 0.002 (8) | −0.010 (7) | −0.007 (7) |
N2R | 0.050 (10) | 0.032 (9) | 0.055 (10) | 0.003 (7) | −0.003 (8) | −0.010 (8) |
C3R | 0.045 (12) | 0.037 (10) | 0.043 (10) | 0.003 (8) | −0.007 (8) | −0.010 (8) |
C4R | 0.049 (11) | 0.042 (12) | 0.044 (11) | 0.005 (8) | −0.002 (9) | −0.007 (8) |
C5R | 0.038 (8) | 0.038 (9) | 0.036 (9) | 0.004 (7) | −0.006 (7) | −0.002 (7) |
C6R | 0.043 (9) | 0.048 (13) | 0.024 (9) | −0.002 (9) | −0.012 (6) | −0.001 (8) |
C2S | 0.037 (9) | 0.037 (11) | 0.031 (9) | 0.004 (8) | −0.007 (7) | −0.003 (7) |
N2S | 0.039 (10) | 0.035 (10) | 0.055 (10) | 0.009 (8) | −0.006 (8) | −0.021 (8) |
C3S | 0.040 (10) | 0.029 (11) | 0.034 (9) | 0.004 (7) | −0.007 (8) | −0.008 (7) |
C4S | 0.037 (12) | 0.039 (12) | 0.039 (11) | 0.002 (9) | 0.006 (9) | −0.010 (8) |
C5S | 0.038 (10) | 0.032 (9) | 0.037 (9) | 0.002 (7) | 0.000 (7) | −0.002 (7) |
C6S | 0.042 (12) | 0.030 (9) | 0.036 (10) | 0.000 (8) | 0.002 (9) | −0.001 (7) |
N1A—C6A | 1.337 (13) | C2I—N2I | 1.316 (13) |
N1A—C2A | 1.350 (12) | C2I—N3I | 1.356 (12) |
C2A—N2A | 1.323 (13) | N2I—H2I1 | 0.881 (5) |
C2A—N3A | 1.360 (12) | N2I—H2I2 | 0.880 (5) |
N2A—H2A1 | 0.880 (5) | N3I—C4I | 1.378 (13) |
N2A—H2A2 | 0.881 (5) | N3I—H3I | 0.880 (5) |
N3A—C4A | 1.380 (13) | C4I—O4I | 1.260 (12) |
N3A—H3A | 0.880 (5) | C4I—C5I | 1.410 (14) |
C4A—O4A | 1.262 (11) | C5I—C6I | 1.361 (14) |
C4A—C5A | 1.418 (13) | C5I—H5I | 0.9500 |
C5A—C6A | 1.361 (14) | C6I—Cl6I | 1.742 (10) |
C5A—H5A | 0.9500 | N1K—C2K | 1.330 (12) |
C6A—Cl6A | 1.742 (10) | N1K—C6K | 1.339 (13) |
N1B—C6B | 1.328 (13) | C2K—N2K | 1.345 (13) |
N1B—C2B | 1.362 (12) | C2K—N3K | 1.349 (13) |
C2B—N2B | 1.325 (13) | N2K—H2K1 | 0.880 (5) |
C2B—N3B | 1.357 (11) | N2K—H2K2 | 0.880 (5) |
N2B—H2B1 | 0.880 (5) | N3K—C4K | 1.382 (13) |
N2B—H2B2 | 0.880 (5) | N3K—H3K | 0.880 (5) |
N3B—C4B | 1.321 (12) | C4K—O4K | 1.240 (11) |
C4B—O4B | 1.300 (11) | C4K—C5K | 1.413 (14) |
C4B—C5B | 1.433 (13) | C5K—C6K | 1.337 (14) |
C5B—C6B | 1.355 (14) | C5K—H5K | 0.9500 |
C5B—H5B | 0.9500 | C6K—Cl6K | 1.754 (10) |
C6B—Cl6B | 1.757 (10) | N1L—C2L | 1.334 (12) |
N1C—C2C | 1.335 (13) | N1L—C6L | 1.376 (12) |
N1C—C6C | 1.347 (13) | C2L—N2L | 1.322 (13) |
C2C—N2C | 1.337 (13) | C2L—N3L | 1.343 (12) |
C2C—N3C | 1.357 (12) | N2L—H2L1 | 0.880 (5) |
N2C—H2C1 | 0.880 (5) | N2L—H2L2 | 0.880 (5) |
N2C—H2C2 | 0.880 (5) | N3L—C4L | 1.412 (12) |
N3C—C4C | 1.404 (13) | N3L—H3L | 0.77 (11) |
N3C—H3C | 0.880 (5) | C4L—O4L | 1.241 (11) |
C4C—O4C | 1.251 (11) | C4L—C5L | 1.412 (13) |
C4C—C5C | 1.398 (14) | C5L—C6L | 1.355 (13) |
C5C—C6C | 1.347 (14) | C5L—H5L | 0.9500 |
C5C—H5C | 0.9500 | C6L—Cl6L | 1.718 (10) |
C6C—Cl6C | 1.743 (10) | N1M—C2M | 1.325 (12) |
N1D—C2D | 1.335 (12) | N1M—C6M | 1.346 (12) |
N1D—C6D | 1.360 (12) | C2M—N3M | 1.352 (12) |
C2D—N2D | 1.335 (12) | C2M—N2M | 1.353 (12) |
C2D—N3D | 1.349 (12) | N2M—H2M1 | 0.880 (5) |
N2D—H2D1 | 0.880 (5) | N2M—H2M2 | 0.880 (5) |
N2D—H2D2 | 0.879 (5) | N3M—C4M | 1.378 (11) |
N3D—C4D | 1.362 (12) | N3M—H3M | 0.96 (11) |
N3D—H3D | 0.880 (5) | C4M—O4M | 1.252 (11) |
C4D—O4D | 1.277 (11) | C4M—C5M | 1.430 (14) |
C4D—C5D | 1.436 (13) | C5M—C6M | 1.345 (14) |
C5D—C6D | 1.342 (14) | C5M—H5M | 0.9500 |
C5D—H5D | 0.9500 | C6M—Cl6M | 1.752 (10) |
C6D—Cl6D | 1.744 (10) | N1O—C2O | 1.326 (13) |
N1E—C2E | 1.324 (12) | N1O—C6O | 1.336 (13) |
N1E—C6E | 1.352 (13) | N1O—H1O | 0.97 (11) |
C2E—N2E | 1.335 (13) | C3O—C4O | 1.349 (15) |
C2E—N3E | 1.359 (12) | C3O—C2O | 1.417 (14) |
N2E—H2E1 | 0.880 (5) | C3O—H3O | 0.9500 |
N2E—H2E2 | 0.880 (5) | C6O—C5O | 1.390 (15) |
N3E—C4E | 1.389 (14) | C6O—H6O | 0.9500 |
N3E—H3E | 0.880 (5) | C2O—N2O | 1.353 (13) |
C4E—O4E | 1.244 (12) | N2O—H2O1 | 0.881 (5) |
C4E—C5E | 1.408 (14) | N2O—H2O2 | 0.881 (5) |
C5E—C6E | 1.375 (13) | C4O—C5O | 1.374 (16) |
C5E—H5E | 0.9500 | C4O—H4O | 0.9500 |
C6E—Cl6E | 1.726 (10) | C5O—H5O | 0.9500 |
N1F—C2F | 1.344 (12) | N1P—C6P | 1.377 (12) |
N1F—C6F | 1.350 (13) | N1P—C2P | 1.400 (11) |
C2F—N2F | 1.319 (13) | N1P—H1P | 0.891 (5) |
C2F—N3F | 1.361 (11) | C2P—N2P | 1.296 (13) |
N2F—H2F1 | 0.881 (5) | C2P—C3P | 1.408 (12) |
N2F—H2F2 | 0.880 (5) | N2P—H2P1 | 0.880 (5) |
N3F—C4F | 1.371 (13) | N2P—H2P2 | 0.880 (5) |
N3F—H3F | 0.880 (5) | C6P—C5P | 1.316 (16) |
C4F—O4F | 1.251 (11) | C6P—H6P | 0.9500 |
C4F—C5F | 1.424 (13) | C5P—C4P | 1.409 (16) |
C5F—C6F | 1.375 (14) | C5P—H5P | 0.9500 |
C5F—H5F | 0.9500 | C4P—C3P | 1.318 (15) |
C6F—Cl6F | 1.723 (10) | C4P—H4P | 0.9500 |
N1G—C6G | 1.331 (12) | C3P—H3P | 0.9500 |
N1G—C2G | 1.366 (12) | N1R—C2S | 1.32 (3) |
C2G—N3G | 1.332 (12) | N1R—C2R | 1.33 (3) |
C2G—N2G | 1.341 (13) | N1R—C6R | 1.35 (3) |
N2G—H2G1 | 0.880 (5) | N1R—C6S | 1.38 (3) |
N2G—H2G2 | 0.880 (5) | C2R—N2R | 1.37 (3) |
N3G—C4G | 1.348 (12) | C2R—C3R | 1.37 (4) |
C4G—O4G | 1.287 (11) | N2R—H2R1 | 0.880 (5) |
C4G—C5G | 1.406 (13) | N2R—H2R2 | 0.880 (5) |
C5G—C6G | 1.361 (13) | C3R—C4R | 1.38 (4) |
C5G—H5G | 0.9500 | C3R—H3R | 0.9500 |
C6G—Cl6G | 1.740 (9) | C4R—C5R | 1.45 (3) |
N1H—C2H | 1.323 (12) | C4R—H4R | 0.9500 |
N1H—C6H | 1.347 (12) | C5R—C6R | 1.30 (3) |
C2H—N2H | 1.335 (12) | C5R—H5R | 0.9500 |
C2H—N3H | 1.350 (12) | C6R—H6R | 0.9500 |
N2H—H2H1 | 0.881 (5) | C2S—C3S | 1.27 (4) |
N2H—H2H2 | 0.880 (5) | C2S—N2S | 1.41 (3) |
N3H—C4H | 1.377 (12) | N2S—H2S1 | 0.880 (5) |
N3H—H3H | 0.880 (5) | N2S—H2S2 | 0.880 (5) |
C4H—O4H | 1.240 (11) | C3S—C4S | 1.35 (4) |
C4H—C5H | 1.430 (13) | C3S—H3S | 0.9500 |
C5H—C6H | 1.359 (13) | C4S—C5S | 1.43 (3) |
C5H—H5H | 0.9500 | C4S—H4S | 0.9500 |
C6H—Cl6H | 1.736 (10) | C5S—C6S | 1.30 (4) |
N1I—C6I | 1.336 (13) | C5S—H5S | 0.9500 |
N1I—C2I | 1.355 (12) | C6S—H6S | 0.9500 |
C6A—N1A—C2A | 115.0 (8) | C2I—N2I—H2I1 | 123.8 (19) |
N2A—C2A—N1A | 118.8 (8) | C2I—N2I—H2I2 | 124.2 (19) |
N2A—C2A—N3A | 119.2 (8) | H2I1—N2I—H2I2 | 112 (4) |
N1A—C2A—N3A | 122.0 (9) | C2I—N3I—C4I | 124.3 (9) |
C2A—N2A—H2A1 | 123.2 (18) | C2I—N3I—H3I | 122 (7) |
C2A—N2A—H2A2 | 123.0 (18) | C4I—N3I—H3I | 114 (7) |
H2A1—N2A—H2A2 | 113 (3) | O4I—C4I—N3I | 118.9 (9) |
C2A—N3A—C4A | 122.8 (8) | O4I—C4I—C5I | 125.3 (10) |
C2A—N3A—H3A | 119 (7) | N3I—C4I—C5I | 115.7 (9) |
C4A—N3A—H3A | 118 (7) | C6I—C5I—C4I | 116.0 (9) |
O4A—C4A—N3A | 118.4 (8) | C6I—C5I—H5I | 122.0 |
O4A—C4A—C5A | 125.7 (9) | C4I—C5I—H5I | 122.0 |
N3A—C4A—C5A | 115.9 (8) | N1I—C6I—C5I | 128.6 (9) |
C6A—C5A—C4A | 116.8 (9) | N1I—C6I—Cl6I | 112.6 (7) |
C6A—C5A—H5A | 121.6 | C5I—C6I—Cl6I | 118.8 (8) |
C4A—C5A—H5A | 121.6 | C2K—N1K—C6K | 114.2 (8) |
N1A—C6A—C5A | 127.5 (9) | N1K—C2K—N2K | 118.7 (9) |
N1A—C6A—Cl6A | 113.7 (7) | N1K—C2K—N3K | 122.6 (9) |
C5A—C6A—Cl6A | 118.8 (8) | N2K—C2K—N3K | 118.7 (9) |
C6B—N1B—C2B | 113.9 (8) | C2K—N2K—H2K1 | 120.8 (18) |
N2B—C2B—N3B | 118.8 (8) | C2K—N2K—H2K2 | 121.0 (18) |
N2B—C2B—N1B | 116.0 (8) | H2K1—N2K—H2K2 | 118 (3) |
N3B—C2B—N1B | 125.2 (9) | C2K—N3K—C4K | 122.9 (8) |
C2B—N2B—H2B1 | 123.0 (18) | C2K—N3K—H3K | 118 (7) |
C2B—N2B—H2B2 | 123.0 (18) | C4K—N3K—H3K | 118 (7) |
H2B1—N2B—H2B2 | 112 (4) | O4K—C4K—N3K | 119.3 (9) |
C4B—N3B—C2B | 118.3 (8) | O4K—C4K—C5K | 125.8 (10) |
O4B—C4B—N3B | 118.7 (8) | N3K—C4K—C5K | 114.9 (8) |
O4B—C4B—C5B | 120.7 (8) | C6K—C5K—C4K | 117.1 (9) |
N3B—C4B—C5B | 120.6 (8) | C6K—C5K—H5K | 121.4 |
C6B—C5B—C4B | 115.3 (9) | C4K—C5K—H5K | 121.4 |
C6B—C5B—H5B | 122.4 | C5K—C6K—N1K | 128.2 (9) |
C4B—C5B—H5B | 122.4 | C5K—C6K—Cl6K | 118.8 (8) |
N1B—C6B—C5B | 126.6 (9) | N1K—C6K—Cl6K | 113.1 (7) |
N1B—C6B—Cl6B | 115.1 (7) | C2L—N1L—C6L | 115.2 (8) |
C5B—C6B—Cl6B | 118.3 (8) | N2L—C2L—N1L | 118.7 (8) |
C2C—N1C—C6C | 114.0 (8) | N2L—C2L—N3L | 119.2 (9) |
N1C—C2C—N2C | 119.2 (8) | N1L—C2L—N3L | 122.1 (9) |
N1C—C2C—N3C | 122.9 (9) | C2L—N2L—H2L1 | 123.6 (19) |
N2C—C2C—N3C | 118.0 (9) | C2L—N2L—H2L2 | 123.4 (19) |
C2C—N2C—H2C1 | 121.9 (18) | H2L1—N2L—H2L2 | 108 (5) |
C2C—N2C—H2C2 | 121.6 (18) | C2L—N3L—C4L | 124.2 (9) |
H2C1—N2C—H2C2 | 116 (4) | C2L—N3L—H3L | 127 (9) |
C2C—N3C—C4C | 122.4 (8) | C4L—N3L—H3L | 109 (9) |
C2C—N3C—H3C | 119 (7) | O4L—C4L—N3L | 118.8 (8) |
C4C—N3C—H3C | 118 (7) | O4L—C4L—C5L | 127.5 (9) |
O4C—C4C—C5C | 127.0 (10) | N3L—C4L—C5L | 113.7 (8) |
O4C—C4C—N3C | 117.8 (9) | C6L—C5L—C4L | 119.0 (9) |
C5C—C4C—N3C | 115.0 (9) | C6L—C5L—H5L | 120.5 |
C6C—C5C—C4C | 117.7 (10) | C4L—C5L—H5L | 120.5 |
C6C—C5C—H5C | 121.1 | C5L—C6L—N1L | 125.8 (9) |
C4C—C5C—H5C | 121.1 | C5L—C6L—Cl6L | 121.2 (8) |
N1C—C6C—C5C | 128.0 (10) | N1L—C6L—Cl6L | 113.0 (7) |
N1C—C6C—Cl6C | 113.4 (7) | C2M—N1M—C6M | 113.3 (8) |
C5C—C6C—Cl6C | 118.6 (8) | N1M—C2M—N3M | 123.5 (9) |
C2D—N1D—C6D | 114.7 (8) | N1M—C2M—N2M | 119.0 (8) |
N2D—C2D—N1D | 118.6 (8) | N3M—C2M—N2M | 117.6 (9) |
N2D—C2D—N3D | 119.2 (8) | C2M—N2M—H2M1 | 120.2 (17) |
N1D—C2D—N3D | 122.2 (8) | C2M—N2M—H2M2 | 120.2 (17) |
C2D—N2D—H2D1 | 121.8 (18) | H2M1—N2M—H2M2 | 120 (3) |
C2D—N2D—H2D2 | 122.2 (18) | C2M—N3M—C4M | 122.4 (9) |
H2D1—N2D—H2D2 | 114 (4) | C2M—N3M—H3M | 121 (6) |
C2D—N3D—C4D | 123.3 (8) | C4M—N3M—H3M | 117 (6) |
C2D—N3D—H3D | 112 (7) | O4M—C4M—N3M | 119.4 (9) |
C4D—N3D—H3D | 125 (7) | O4M—C4M—C5M | 124.4 (9) |
O4D—C4D—N3D | 120.3 (9) | N3M—C4M—C5M | 116.2 (9) |
O4D—C4D—C5D | 123.6 (9) | C6M—C5M—C4M | 114.9 (9) |
N3D—C4D—C5D | 116.1 (8) | C6M—C5M—H5M | 122.5 |
C6D—C5D—C4D | 116.0 (9) | C4M—C5M—H5M | 122.5 |
C6D—C5D—H5D | 122.0 | C5M—C6M—N1M | 129.8 (10) |
C4D—C5D—H5D | 122.0 | C5M—C6M—Cl6M | 117.8 (8) |
C5D—C6D—N1D | 127.6 (9) | N1M—C6M—Cl6M | 112.4 (7) |
C5D—C6D—Cl6D | 119.5 (8) | C2O—N1O—C6O | 121.3 (9) |
N1D—C6D—Cl6D | 112.9 (7) | C2O—N1O—H1O | 124 (7) |
C2E—N1E—C6E | 115.7 (8) | C6O—N1O—H1O | 115 (7) |
N1E—C2E—N2E | 119.1 (8) | C4O—C3O—C2O | 118.9 (9) |
N1E—C2E—N3E | 122.4 (9) | C4O—C3O—H3O | 120.5 |
N2E—C2E—N3E | 118.6 (8) | C2O—C3O—H3O | 120.5 |
C2E—N2E—H2E1 | 122.2 (18) | N1O—C6O—C5O | 121.2 (9) |
C2E—N2E—H2E2 | 121.8 (18) | N1O—C6O—H6O | 119.4 |
H2E1—N2E—H2E2 | 116 (3) | C5O—C6O—H6O | 119.4 |
C2E—N3E—C4E | 122.9 (8) | N1O—C2O—N2O | 119.7 (9) |
C2E—N3E—H3E | 123 (7) | N1O—C2O—C3O | 119.6 (9) |
C4E—N3E—H3E | 114 (7) | N2O—C2O—C3O | 120.7 (9) |
O4E—C4E—N3E | 117.6 (9) | C2O—N2O—H2O1 | 120.2 (18) |
O4E—C4E—C5E | 126.9 (10) | C2O—N2O—H2O2 | 120.0 (18) |
N3E—C4E—C5E | 115.5 (9) | H2O1—N2O—H2O2 | 114 (6) |
C6E—C5E—C4E | 117.4 (9) | C3O—C4O—C5O | 121.1 (9) |
C6E—C5E—H5E | 121.3 | C3O—C4O—H4O | 119.5 |
C4E—C5E—H5E | 121.3 | C5O—C4O—H4O | 119.5 |
N1E—C6E—C5E | 126.1 (9) | C4O—C5O—C6O | 117.8 (10) |
N1E—C6E—Cl6E | 113.9 (7) | C4O—C5O—H5O | 121.1 |
C5E—C6E—Cl6E | 120.0 (8) | C6O—C5O—H5O | 121.1 |
C2F—N1F—C6F | 115.6 (8) | C6P—N1P—C2P | 119.0 (7) |
N2F—C2F—N1F | 119.7 (8) | C6P—N1P—H1P | 116.3 (11) |
N2F—C2F—N3F | 119.0 (8) | C2P—N1P—H1P | 124.7 (12) |
N1F—C2F—N3F | 121.2 (9) | N2P—C2P—N1P | 117.3 (8) |
C2F—N2F—H2F1 | 123.6 (19) | N2P—C2P—C3P | 125.7 (9) |
C2F—N2F—H2F2 | 123.8 (19) | N1P—C2P—C3P | 117.0 (9) |
H2F1—N2F—H2F2 | 112 (4) | C2P—N2P—H2P1 | 126 (2) |
C2F—N3F—C4F | 124.6 (8) | C2P—N2P—H2P2 | 126 (2) |
C2F—N3F—H3F | 123 (7) | H2P1—N2P—H2P2 | 107 (4) |
C4F—N3F—H3F | 112 (7) | C5P—C6P—N1P | 124.5 (10) |
O4F—C4F—N3F | 120.7 (9) | C5P—C6P—H6P | 117.8 |
O4F—C4F—C5F | 124.6 (10) | N1P—C6P—H6P | 117.8 |
N3F—C4F—C5F | 114.7 (8) | C6P—C5P—C4P | 115.9 (11) |
C6F—C5F—C4F | 117.6 (9) | C6P—C5P—H4P | 122.0 |
C6F—C5F—H5F | 121.2 | C4P—C5P—H4P | 122.0 |
C4F—C5F—H5F | 121.2 | C3P—C4P—C5P | 123.2 (10) |
N1F—C6F—C5F | 126.1 (9) | C3P—C4P—H4P | 118.4 |
N1F—C6F—Cl6F | 114.4 (7) | C5P—C4P—H4P | 118.4 |
C5F—C6F—Cl6F | 119.4 (8) | C4P—C3P—C2P | 120.4 (10) |
C6G—N1G—C2G | 113.9 (8) | C4P—C3P—H3P | 119.8 |
N3G—C2G—N2G | 118.6 (9) | C2P—C3P—H3P | 119.8 |
N3G—C2G—N1G | 125.4 (9) | C2R—N1R—C6R | 109.7 (17) |
N2G—C2G—N1G | 115.9 (8) | C2S—N1R—C6S | 108.3 (17) |
C2G—N2G—H2G1 | 121.4 (18) | N1R—C2R—N2R | 113 (2) |
C2G—N2G—H2G2 | 121.4 (18) | N1R—C2R—C3R | 130 (3) |
H2G1—N2G—H2G2 | 109 (6) | N2R—C2R—C3R | 118 (3) |
C2G—N3G—C4G | 118.6 (8) | C2R—N2R—H2R1 | 118 (3) |
O4G—C4G—N3G | 118.9 (9) | C2R—N2R—H2R2 | 118 (3) |
O4G—C4G—C5G | 121.3 (9) | H2R1—N2R—H2R2 | 122 (8) |
N3G—C4G—C5G | 119.8 (9) | C2R—C3R—C4R | 114 (3) |
C6G—C5G—C4G | 116.4 (9) | C2R—C3R—H3R | 122.9 |
C6G—C5G—H5G | 121.8 | C4R—C3R—H3R | 122.9 |
C4G—C5G—H5G | 121.8 | C3R—C4R—C5R | 121 (3) |
N1G—C6G—C5G | 125.8 (9) | C3R—C4R—H4R | 119.7 |
N1G—C6G—Cl6G | 113.7 (7) | C5R—C4R—H4R | 119.7 |
C5G—C6G—Cl6G | 120.5 (8) | C6R—C5R—C4R | 114 (2) |
C2H—N1H—C6H | 115.6 (8) | C6R—C5R—H5R | 123.0 |
N1H—C2H—N2H | 118.8 (8) | C4R—C5R—H5R | 123.0 |
N1H—C2H—N3H | 122.3 (9) | C5R—C6R—N1R | 132 (2) |
N2H—C2H—N3H | 118.8 (9) | C5R—C6R—H6R | 114.2 |
C2H—N2H—H2H1 | 121.7 (18) | N1R—C6R—H6R | 114.2 |
C2H—N2H—H2H2 | 122.1 (18) | C3S—C2S—N1R | 131 (3) |
H2H1—N2H—H2H2 | 116 (3) | C3S—C2S—N2S | 120 (3) |
C2H—N3H—C4H | 123.3 (8) | N1R—C2S—N2S | 109 (2) |
C2H—N3H—H3H | 116 (7) | C2S—N2S—H2S1 | 115 (3) |
C4H—N3H—H3H | 121 (7) | C2S—N2S—H2S2 | 115 (3) |
O4H—C4H—N3H | 120.8 (8) | H2S1—N2S—H2S2 | 124 (10) |
O4H—C4H—C5H | 123.8 (8) | C2S—C3S—C4S | 115 (3) |
N3H—C4H—C5H | 115.3 (8) | C2S—C3S—H3S | 122.3 |
C6H—C5H—C4H | 116.5 (9) | C4S—C3S—H3S | 122.3 |
C6H—C5H—H5H | 121.7 | C3S—C4S—C5S | 123 (3) |
C4H—C5H—H5H | 121.7 | C3S—C4S—H4S | 118.7 |
N1H—C6H—C5H | 126.9 (9) | C5S—C4S—H4S | 118.7 |
N1H—C6H—Cl6H | 114.2 (7) | C6S—C5S—C4S | 111 (3) |
C5H—C6H—Cl6H | 118.8 (7) | C6S—C5S—H5S | 124.6 |
C6I—N1I—C2I | 114.8 (8) | C4S—C5S—H5S | 124.6 |
N2I—C2I—N1I | 119.8 (9) | C5S—C6S—N1R | 131 (2) |
N2I—C2I—N3I | 119.6 (9) | C5S—C6S—H6S | 114.6 |
N1I—C2I—N3I | 120.5 (9) | N1R—C6S—H6S | 114.6 |
C6A—N1A—C2A—N2A | −178.3 (10) | C4H—C5H—C6H—N1H | 2.1 (16) |
C6A—N1A—C2A—N3A | 2.3 (15) | C4H—C5H—C6H—Cl6H | 179.5 (7) |
N2A—C2A—N3A—C4A | −179.0 (10) | C6I—N1I—C2I—N2I | 178.7 (10) |
N1A—C2A—N3A—C4A | 0.3 (15) | C6I—N1I—C2I—N3I | 0.3 (14) |
C2A—N3A—C4A—O4A | 178.2 (9) | N2I—C2I—N3I—C4I | −179.4 (10) |
C2A—N3A—C4A—C5A | −2.5 (14) | N1I—C2I—N3I—C4I | −0.9 (15) |
O4A—C4A—C5A—C6A | −178.8 (10) | C2I—N3I—C4I—O4I | −179.5 (9) |
N3A—C4A—C5A—C6A | 1.9 (14) | C2I—N3I—C4I—C5I | 1.8 (14) |
C2A—N1A—C6A—C5A | −2.9 (16) | O4I—C4I—C5I—C6I | 179.5 (10) |
C2A—N1A—C6A—Cl6A | 177.1 (7) | N3I—C4I—C5I—C6I | −1.9 (13) |
C4A—C5A—C6A—N1A | 0.8 (17) | C2I—N1I—C6I—C5I | −0.7 (16) |
C4A—C5A—C6A—Cl6A | −179.2 (8) | C2I—N1I—C6I—Cl6I | 178.9 (7) |
C6B—N1B—C2B—N2B | −178.5 (9) | C4I—C5I—C6I—N1I | 1.5 (16) |
C6B—N1B—C2B—N3B | 0.1 (14) | C4I—C5I—C6I—Cl6I | −178.0 (7) |
N2B—C2B—N3B—C4B | 179.1 (9) | C6K—N1K—C2K—N2K | 178.9 (9) |
N1B—C2B—N3B—C4B | 0.5 (15) | C6K—N1K—C2K—N3K | −2.2 (14) |
C2B—N3B—C4B—O4B | 180.0 (9) | N1K—C2K—N3K—C4K | 2.6 (15) |
C2B—N3B—C4B—C5B | −1.3 (14) | N2K—C2K—N3K—C4K | −178.5 (9) |
O4B—C4B—C5B—C6B | −179.8 (10) | C2K—N3K—C4K—O4K | −179.8 (9) |
N3B—C4B—C5B—C6B | 1.5 (15) | C2K—N3K—C4K—C5K | −1.5 (14) |
C2B—N1B—C6B—C5B | 0.1 (16) | O4K—C4K—C5K—C6K | 178.5 (10) |
C2B—N1B—C6B—Cl6B | −179.9 (7) | N3K—C4K—C5K—C6K | 0.4 (14) |
C4B—C5B—C6B—N1B | −0.9 (17) | C4K—C5K—C6K—N1K | −0.2 (17) |
C4B—C5B—C6B—Cl6B | 179.1 (8) | C4K—C5K—C6K—Cl6K | 179.8 (7) |
C6C—N1C—C2C—N2C | 179.7 (10) | C2K—N1K—C6K—C5K | 1.1 (15) |
C6C—N1C—C2C—N3C | 0.6 (15) | C2K—N1K—C6K—Cl6K | −178.9 (7) |
N1C—C2C—N3C—C4C | −0.9 (16) | C6L—N1L—C2L—N2L | 179.3 (9) |
N2C—C2C—N3C—C4C | −180.0 (9) | C6L—N1L—C2L—N3L | −0.9 (14) |
C2C—N3C—C4C—O4C | 177.5 (9) | N2L—C2L—N3L—C4L | −179.9 (9) |
C2C—N3C—C4C—C5C | 2.6 (14) | N1L—C2L—N3L—C4L | 0.3 (15) |
O4C—C4C—C5C—C6C | −178.4 (10) | C2L—N3L—C4L—O4L | −178.4 (9) |
N3C—C4C—C5C—C6C | −4.1 (14) | C2L—N3L—C4L—C5L | 1.2 (14) |
C2C—N1C—C6C—C5C | −2.6 (16) | O4L—C4L—C5L—C6L | 177.5 (9) |
C2C—N1C—C6C—Cl6C | 177.8 (7) | N3L—C4L—C5L—C6L | −2.0 (13) |
C4C—C5C—C6C—N1C | 4.5 (17) | C4L—C5L—C6L—N1L | 1.7 (15) |
C4C—C5C—C6C—Cl6C | −175.9 (8) | C4L—C5L—C6L—Cl6L | −176.4 (7) |
C6D—N1D—C2D—N2D | 178.7 (9) | C2L—N1L—C6L—C5L | −0.1 (15) |
C6D—N1D—C2D—N3D | 0.7 (14) | C2L—N1L—C6L—Cl6L | 178.1 (7) |
N2D—C2D—N3D—C4D | −177.5 (10) | C6M—N1M—C2M—N3M | −0.2 (14) |
N1D—C2D—N3D—C4D | 0.5 (15) | C6M—N1M—C2M—N2M | 179.4 (9) |
C2D—N3D—C4D—O4D | 177.0 (9) | N1M—C2M—N3M—C4M | −0.2 (15) |
C2D—N3D—C4D—C5D | −0.8 (14) | N2M—C2M—N3M—C4M | −179.9 (9) |
O4D—C4D—C5D—C6D | −177.7 (10) | C2M—N3M—C4M—O4M | −178.6 (9) |
N3D—C4D—C5D—C6D | 0.1 (14) | C2M—N3M—C4M—C5M | 1.3 (13) |
C4D—C5D—C6D—N1D | 1.2 (16) | O4M—C4M—C5M—C6M | 178.0 (10) |
C4D—C5D—C6D—Cl6D | −179.2 (7) | N3M—C4M—C5M—C6M | −1.9 (13) |
C2D—N1D—C6D—C5D | −1.6 (15) | C4M—C5M—C6M—N1M | 1.7 (17) |
C2D—N1D—C6D—Cl6D | 178.8 (7) | C4M—C5M—C6M—Cl6M | 179.5 (7) |
C6E—N1E—C2E—N2E | 179.2 (10) | C2M—N1M—C6M—C5M | −0.6 (16) |
C6E—N1E—C2E—N3E | 0.4 (15) | C2M—N1M—C6M—Cl6M | −178.5 (7) |
N1E—C2E—N3E—C4E | −0.9 (16) | C2O—N1O—C6O—C5O | −0.3 (14) |
N2E—C2E—N3E—C4E | −179.6 (10) | C6O—N1O—C2O—N2O | −179.4 (10) |
C2E—N3E—C4E—O4E | −178.6 (10) | C6O—N1O—C2O—C3O | 2.8 (14) |
C2E—N3E—C4E—C5E | 1.2 (15) | C4O—C3O—C2O—N1O | −2.5 (14) |
O4E—C4E—C5E—C6E | 178.7 (11) | C4O—C3O—C2O—N2O | 179.6 (10) |
N3E—C4E—C5E—C6E | −1.1 (15) | C2O—C3O—C4O—C5O | −0.2 (15) |
C2E—N1E—C6E—C5E | −0.4 (16) | C3O—C4O—C5O—C6O | 2.5 (15) |
C2E—N1E—C6E—Cl6E | 179.2 (7) | N1O—C6O—C5O—C4O | −2.3 (15) |
C4E—C5E—C6E—N1E | 0.8 (16) | C6P—N1P—C2P—N2P | −178.7 (9) |
C4E—C5E—C6E—Cl6E | −178.9 (8) | C6P—N1P—C2P—C3P | 1.3 (13) |
C6F—N1F—C2F—N2F | −179.7 (10) | C2P—N1P—C6P—C5P | −1.2 (15) |
C6F—N1F—C2F—N3F | −1.8 (14) | N1P—C6P—C5P—C4P | −0.2 (16) |
N2F—C2F—N3F—C4F | 177.6 (10) | C6P—C5P—C4P—C3P | 1.6 (16) |
N1F—C2F—N3F—C4F | −0.4 (16) | C5P—C4P—C3P—C2P | −1.6 (16) |
C2F—N3F—C4F—O4F | −179.4 (10) | N2P—C2P—C3P—C4P | −180.0 (10) |
C2F—N3F—C4F—C5F | 1.5 (15) | N1P—C2P—C3P—C4P | 0.0 (14) |
O4F—C4F—C5F—C6F | −179.5 (10) | C2S—N1R—C2R—N2R | 177.6 (13) |
N3F—C4F—C5F—C6F | −0.4 (15) | C6R—N1R—C2R—N2R | −173.9 (13) |
C2F—N1F—C6F—C5F | 2.9 (15) | C6S—N1R—C2R—N2R | 15 (3) |
C2F—N1F—C6F—Cl6F | −178.6 (7) | C2S—N1R—C2R—C3R | 0 (2) |
C4F—C5F—C6F—N1F | −1.8 (17) | C6R—N1R—C2R—C3R | 9 (2) |
C4F—C5F—C6F—Cl6F | 179.8 (8) | C6S—N1R—C2R—C3R | −162 (4) |
C6G—N1G—C2G—N3G | 2.2 (14) | N1R—C2R—C3R—C4R | −7 (4) |
C6G—N1G—C2G—N2G | −180.0 (9) | N2R—C2R—C3R—C4R | 176 (2) |
N2G—C2G—N3G—C4G | −175.7 (9) | C2R—C3R—C4R—C5R | 1 (4) |
N1G—C2G—N3G—C4G | 2.1 (15) | C3R—C4R—C5R—C6R | 1 (4) |
C2G—N3G—C4G—O4G | 177.3 (9) | C4R—C5R—C6R—N1R | 1 (3) |
C2G—N3G—C4G—C5G | −4.5 (14) | C2S—N1R—C6R—C5R | 14 (3) |
O4G—C4G—C5G—C6G | −179.3 (9) | C2R—N1R—C6R—C5R | −6 (3) |
N3G—C4G—C5G—C6G | 2.6 (15) | C6S—N1R—C6R—C5R | −1 (4) |
C2G—N1G—C6G—C5G | −4.3 (14) | C2R—N1R—C2S—C3S | 7 (3) |
C2G—N1G—C6G—Cl6G | 178.2 (7) | C6R—N1R—C2S—C3S | −154 (7) |
C4G—C5G—C6G—N1G | 2.1 (15) | C6S—N1R—C2S—C3S | 14 (4) |
C4G—C5G—C6G—Cl6G | 179.4 (8) | C2R—N1R—C2S—N2S | 178.4 (18) |
C6H—N1H—C2H—N2H | 178.6 (9) | C6R—N1R—C2S—N2S | 17 (3) |
C6H—N1H—C2H—N3H | 1.6 (14) | C6S—N1R—C2S—N2S | −174.5 (18) |
N1H—C2H—N3H—C4H | −3.5 (15) | N1R—C2S—C3S—C4S | −12 (5) |
N2H—C2H—N3H—C4H | 179.6 (9) | N2S—C2S—C3S—C4S | 178 (3) |
C2H—N3H—C4H—O4H | −178.7 (9) | C2S—C3S—C4S—C5S | 3 (5) |
C2H—N3H—C4H—C5H | 4.2 (14) | C3S—C4S—C5S—C6S | 1 (4) |
O4H—C4H—C5H—C6H | 179.6 (9) | C4S—C5S—C6S—N1R | 3 (4) |
N3H—C4H—C5H—C6H | −3.4 (13) | C2S—N1R—C6S—C5S | −9 (3) |
C2H—N1H—C6H—C5H | −1.1 (15) | C2R—N1R—C6S—C5S | 9.1 (17) |
C2H—N1H—C6H—Cl6H | −178.6 (7) | C6R—N1R—C6S—C5S | −2 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2A—H2A1···N1Fi | 0.88 (1) | 2.25 (2) | 3.107 (11) | 166 (6) |
N2A—H2A2···O4B | 0.88 (1) | 1.95 (2) | 2.829 (11) | 173 (5) |
N3A—H3A···N3B | 0.88 (1) | 2.03 (3) | 2.900 (11) | 168 (10) |
N2B—H2B1···O4A | 0.88 (1) | 2.09 (2) | 2.960 (11) | 169 (3) |
N2B—H2B2···N1C | 0.88 (1) | 2.28 (2) | 3.140 (11) | 167 (7) |
N2C—H2C1···N1B | 0.88 (1) | 2.09 (4) | 2.936 (11) | 160 (11) |
N3C—H3C···O4D | 0.88 (1) | 1.96 (2) | 2.839 (11) | 175 (11) |
N2D—H2D1···N1E | 0.88 (1) | 2.13 (2) | 2.991 (11) | 167 (6) |
N3D—H3D···O4C | 0.88 (1) | 1.86 (2) | 2.732 (10) | 169 (10) |
C5D—H5D···Cl6Gii | 0.95 | 2.88 | 3.769 (11) | 156 |
N2E—H2E1···N1D | 0.88 (1) | 2.05 (2) | 2.917 (11) | 169 (5) |
N3E—H3E···O4F | 0.88 (1) | 1.92 (3) | 2.772 (11) | 164 (11) |
N2F—H2F1···N1Aiii | 0.88 (1) | 2.06 (2) | 2.930 (11) | 171 (6) |
N2F—H2F2···N2R | 0.88 (1) | 2.44 (4) | 3.29 (2) | 162 (9) |
N3F—H3F···O4E | 0.88 (1) | 1.90 (3) | 2.761 (11) | 166 (10) |
N2G—H2G1···O4H | 0.88 (1) | 2.03 (3) | 2.892 (11) | 166 (10) |
N2G—H2G2···N1Miv | 0.88 (1) | 2.27 (3) | 3.120 (11) | 162 (9) |
C5G—H5G···Cl6Dii | 0.95 | 2.73 | 3.638 (10) | 161 |
N2H—H2H1···N1I | 0.88 (1) | 2.18 (2) | 3.045 (11) | 169 (3) |
N2H—H2H2···O4G | 0.88 (1) | 1.97 (2) | 2.842 (11) | 175 (9) |
N3H—H3H···N3G | 0.88 (1) | 2.00 (2) | 2.870 (11) | 169 (10) |
C5H—H5H···Cl6Ev | 0.95 | 2.93 | 3.837 (10) | 161 |
N2I—H2I1···N1H | 0.88 (1) | 2.04 (3) | 2.900 (12) | 165 (9) |
N3I—H3I···O4K | 0.88 (1) | 1.89 (2) | 2.764 (11) | 173 (10) |
N2K—H2K2···N2Svi | 0.88 (1) | 2.28 (4) | 3.13 (2) | 161 (8) |
N3K—H3K···O4I | 0.88 (1) | 1.88 (1) | 2.761 (11) | 176 (10) |
N2L—H2L1···N1K | 0.88 (1) | 2.14 (3) | 2.999 (11) | 164 (9) |
N2L—H2L2···N2O | 0.88 (1) | 2.59 (4) | 3.436 (14) | 162 (10) |
N3L—H3L···O4M | 0.77 (11) | 2.02 (12) | 2.782 (11) | 169 (12) |
N2M—H2M1···N1Gvii | 0.88 (1) | 2.05 (1) | 2.927 (11) | 175 (6) |
N3M—H3M···O4L | 0.96 (11) | 1.83 (11) | 2.794 (11) | 175 (10) |
N1O—H1O···O4Gviii | 0.97 (11) | 1.64 (12) | 2.598 (11) | 167 (10) |
N2O—H2O1···O4M | 0.88 (1) | 1.98 (1) | 2.810 (12) | 157 (3) |
N2O—H2O2···N1Rix | 0.88 (1) | 2.27 (8) | 2.971 (13) | 136 (10) |
N1P—H1P···O4Ax | 0.89 (1) | 2.01 (1) | 2.769 (10) | 143 (2) |
N2P—H2P1···O4B | 0.88 (1) | 1.89 (3) | 2.719 (11) | 157 (8) |
N2P—H2P2···O4H | 0.88 (1) | 2.11 (5) | 2.872 (11) | 144 (7) |
C3P—H3P···O4Lviii | 0.95 | 2.49 | 3.186 (11) | 130 |
N2R—H2R1···O4Fxi | 0.88 (1) | 2.36 (5) | 3.05 (2) | 136 (6) |
N2R—H2R2···O4E | 0.88 (1) | 2.12 (6) | 2.92 (2) | 152 (12) |
C3R—H3R···O4Dxii | 0.95 | 2.44 | 3.37 (4) | 167 |
C5R—H5R···O4Ixiii | 0.95 | 2.45 | 3.28 (2) | 145 |
C4O—H4O···O4Cxiv | 0.95 | 2.64 | 3.577 (12) | 171 |
Symmetry codes: (i) x−1, y+2, z; (ii) −x+2, −y−1, −z+1; (iii) x+1, y−2, z; (iv) x+2, y−1, z; (v) −x+2, −y−1, −z; (vi) x−2, y+2, z+1; (vii) x−2, y+1, z; (viii) −x, −y+1, −z+1; (ix) −x+1, −y−1, −z; (x) −x+2, −y, −z; (xi) −x+3, −y−3, −z; (xii) −x+3, −y−2, −z; (xiii) x+2, y−2, z−1; (xiv) −x+1, −y, −z. |
C5H6BrN3O | F(000) = 800 |
Mr = 204.04 | Dx = 2.034 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 9.8154 (13) Å | Cell parameters from 6792 reflections |
b = 9.9532 (8) Å | θ = 3.6–26.1° |
c = 14.344 (2) Å | µ = 6.10 mm−1 |
β = 108.021 (11)° | T = 173 K |
V = 1332.6 (3) Å3 | Block, colourless |
Z = 8 | 0.35 × 0.30 × 0.25 mm |
Stoe IPDSII two-circle diffractometer | 1986 reflections with I > 2σ(I) |
Radiation source: Genix 3D IµS microfocus X-ray source | Rint = 0.103 |
ω scans | θmax = 25.7°, θmin = 3.6° |
Absorption correction: multi-scan X-AREA (Stoe & Cie, 2001) | h = −11→11 |
Tmin = 0.220, Tmax = 0.310 | k = −12→10 |
6144 measured reflections | l = −17→17 |
2480 independent reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.076 | Hydrogen site location: mixed |
wR(F2) = 0.228 | H 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 parameters | Δρmax = 1.06 e Å−3 |
11 restraints | Δρmin = −1.50 e Å−3 |
C5H6BrN3O | V = 1332.6 (3) Å3 |
Mr = 204.04 | Z = 8 |
Monoclinic, P21/n | Mo Kα radiation |
a = 9.8154 (13) Å | µ = 6.10 mm−1 |
b = 9.9532 (8) Å | T = 173 K |
c = 14.344 (2) Å | 0.35 × 0.30 × 0.25 mm |
β = 108.021 (11)° |
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 = 0.310 | Rint = 0.103 |
6144 measured reflections |
R[F2 > 2σ(F2)] = 0.076 | 11 restraints |
wR(F2) = 0.228 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | Δρmax = 1.06 e Å−3 |
2480 reflections | Δρmin = −1.50 e Å−3 |
201 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
N1A | 0.4704 (7) | 0.8846 (7) | 0.3227 (4) | 0.0251 (14) | |
H1A | 0.425 (9) | 0.904 (9) | 0.261 (3) | 0.030* | |
C2A | 0.4096 (8) | 0.7796 (8) | 0.3524 (5) | 0.0239 (16) | |
N2A | 0.2973 (8) | 0.7214 (7) | 0.2890 (5) | 0.0317 (17) | |
H2A1 | 0.240 (9) | 0.672 (9) | 0.311 (7) | 0.038* | |
H2A2 | 0.275 (11) | 0.744 (10) | 0.227 (3) | 0.038* | |
N3A | 0.4543 (7) | 0.7329 (7) | 0.4441 (4) | 0.0238 (14) | |
C4A | 0.5692 (8) | 0.7914 (8) | 0.5109 (5) | 0.0232 (16) | |
O4A | 0.6128 (6) | 0.7470 (6) | 0.5970 (3) | 0.0246 (12) | |
C5A | 0.6353 (8) | 0.9042 (8) | 0.4775 (5) | 0.0246 (16) | |
Br5A | 0.79004 (11) | 0.98982 (11) | 0.56837 (7) | 0.0460 (4) | |
C6A | 0.5873 (8) | 0.9487 (8) | 0.3859 (6) | 0.0239 (16) | |
C61A | 0.6417 (10) | 1.0653 (9) | 0.3425 (6) | 0.0326 (19) | |
H61A | 0.7055 | 1.1195 | 0.3950 | 0.049* | |
H61B | 0.5607 | 1.1205 | 0.3047 | 0.049* | |
H61C | 0.6945 | 1.0325 | 0.2992 | 0.049* | |
N1B | 0.2832 (8) | 0.3906 (7) | 0.6420 (4) | 0.0275 (14) | |
C2B | 0.3494 (8) | 0.4851 (7) | 0.6073 (5) | 0.0227 (16) | |
N2B | 0.4640 (8) | 0.5476 (7) | 0.6676 (5) | 0.0311 (16) | |
H2B1 | 0.501 (4) | 0.520 (4) | 0.7294 (16) | 0.037* | |
H2B2 | 0.507 (7) | 0.613 (7) | 0.645 (3) | 0.037* | |
N3B | 0.3046 (7) | 0.5243 (7) | 0.5121 (4) | 0.0228 (14) | |
H3B | 0.364 (8) | 0.577 (8) | 0.495 (6) | 0.027* | |
C4B | 0.1891 (8) | 0.4675 (8) | 0.4436 (5) | 0.0225 (16) | |
O4B | 0.1563 (6) | 0.5068 (5) | 0.3564 (4) | 0.0257 (12) | |
C5B | 0.1158 (9) | 0.3701 (8) | 0.4818 (5) | 0.0271 (17) | |
Br5B | −0.04808 (10) | 0.29445 (10) | 0.39310 (6) | 0.0411 (4) | |
C6B | 0.1655 (9) | 0.3341 (8) | 0.5791 (5) | 0.0267 (17) | |
C61B | 0.0923 (11) | 0.2293 (9) | 0.6207 (6) | 0.0339 (19) | |
H61D | 0.1518 | 0.2072 | 0.6875 | 0.051* | |
H61E | 0.0778 | 0.1485 | 0.5798 | 0.051* | |
H61F | −0.0006 | 0.2635 | 0.6222 | 0.051* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1A | 0.029 (3) | 0.033 (3) | 0.011 (3) | 0.000 (3) | 0.002 (2) | 0.006 (2) |
C2A | 0.023 (4) | 0.032 (4) | 0.011 (3) | 0.003 (3) | −0.003 (3) | 0.000 (3) |
N2A | 0.034 (4) | 0.039 (4) | 0.011 (3) | −0.010 (3) | −0.009 (3) | 0.008 (3) |
N3A | 0.032 (4) | 0.028 (3) | 0.009 (3) | −0.003 (3) | 0.001 (2) | 0.002 (2) |
C4A | 0.022 (4) | 0.030 (4) | 0.013 (3) | 0.004 (3) | 0.000 (3) | −0.003 (3) |
O4A | 0.026 (3) | 0.033 (3) | 0.009 (2) | −0.001 (2) | −0.003 (2) | 0.003 (2) |
C5A | 0.022 (4) | 0.030 (4) | 0.019 (3) | −0.004 (3) | 0.002 (3) | 0.000 (3) |
Br5A | 0.0473 (7) | 0.0508 (6) | 0.0325 (6) | −0.0059 (4) | 0.0017 (4) | −0.0039 (4) |
C6A | 0.020 (4) | 0.026 (4) | 0.024 (4) | 0.000 (3) | 0.006 (3) | −0.001 (3) |
C61A | 0.035 (4) | 0.032 (4) | 0.031 (4) | −0.002 (3) | 0.010 (3) | 0.011 (3) |
N1B | 0.036 (4) | 0.030 (3) | 0.016 (3) | 0.006 (3) | 0.008 (3) | 0.003 (3) |
C2B | 0.025 (4) | 0.024 (4) | 0.017 (3) | 0.000 (3) | 0.005 (3) | −0.002 (3) |
N2B | 0.039 (4) | 0.035 (4) | 0.015 (3) | −0.003 (3) | 0.001 (3) | −0.001 (3) |
N3B | 0.023 (3) | 0.029 (3) | 0.015 (3) | −0.004 (3) | 0.003 (2) | −0.001 (2) |
C4B | 0.024 (4) | 0.024 (3) | 0.016 (3) | 0.003 (3) | 0.002 (3) | −0.002 (3) |
O4B | 0.027 (3) | 0.036 (3) | 0.011 (2) | −0.004 (2) | 0.002 (2) | 0.000 (2) |
C5B | 0.031 (4) | 0.032 (4) | 0.018 (3) | 0.001 (3) | 0.008 (3) | −0.002 (3) |
Br5B | 0.0366 (6) | 0.0474 (6) | 0.0333 (5) | −0.0106 (4) | 0.0020 (4) | −0.0013 (4) |
C6B | 0.040 (5) | 0.025 (4) | 0.016 (3) | 0.000 (3) | 0.011 (3) | −0.005 (3) |
C61B | 0.041 (5) | 0.035 (4) | 0.026 (4) | −0.006 (4) | 0.012 (4) | 0.000 (3) |
N1A—C2A | 1.337 (11) | N1B—C2B | 1.325 (11) |
N1A—C6A | 1.380 (10) | N1B—C6B | 1.349 (10) |
N1A—H1A | 0.88 (2) | C2B—N2B | 1.342 (10) |
C2A—N2A | 1.325 (10) | C2B—N3B | 1.355 (10) |
C2A—N3A | 1.335 (9) | N2B—H2B1 | 0.891 (16) |
N2A—H2A1 | 0.87 (2) | N2B—H2B2 | 0.894 (16) |
N2A—H2A2 | 0.88 (2) | N3B—C4B | 1.372 (9) |
N3A—C4A | 1.365 (9) | N3B—H3B | 0.87 (2) |
C4A—O4A | 1.256 (9) | C4B—O4B | 1.254 (9) |
C4A—C5A | 1.450 (11) | C4B—C5B | 1.415 (12) |
C5A—C6A | 1.327 (11) | C5B—C6B | 1.376 (10) |
C5A—Br5A | 1.873 (7) | C5B—Br5B | 1.873 (8) |
C6A—C61A | 1.492 (11) | C6B—C61B | 1.491 (12) |
C61A—H61A | 0.9800 | C61B—H61D | 0.9800 |
C61A—H61B | 0.9800 | C61B—H61E | 0.9800 |
C61A—H61C | 0.9800 | C61B—H61F | 0.9800 |
C2A—N1A—C6A | 121.0 (6) | C2B—N1B—C6B | 117.6 (6) |
C2A—N1A—H1A | 111 (6) | N1B—C2B—N2B | 119.8 (7) |
C6A—N1A—H1A | 128 (6) | N1B—C2B—N3B | 122.6 (7) |
N2A—C2A—N3A | 118.3 (7) | N2B—C2B—N3B | 117.6 (7) |
N2A—C2A—N1A | 118.8 (6) | C2B—N2B—H2B1 | 120.1 (16) |
N3A—C2A—N1A | 122.9 (7) | C2B—N2B—H2B2 | 120.0 (16) |
C2A—N2A—H2A1 | 120 (7) | H2B1—N2B—H2B2 | 119.8 (15) |
C2A—N2A—H2A2 | 118 (7) | C2B—N3B—C4B | 122.8 (7) |
H2A1—N2A—H2A2 | 121 (10) | C2B—N3B—H3B | 115 (6) |
C2A—N3A—C4A | 119.5 (7) | C4B—N3B—H3B | 122 (6) |
O4A—C4A—N3A | 119.8 (7) | O4B—C4B—N3B | 119.2 (7) |
O4A—C4A—C5A | 123.1 (6) | O4B—C4B—C5B | 126.6 (7) |
N3A—C4A—C5A | 117.1 (6) | N3B—C4B—C5B | 114.2 (6) |
C6A—C5A—C4A | 121.9 (7) | C6B—C5B—C4B | 120.6 (7) |
C6A—C5A—Br5A | 120.0 (6) | C6B—C5B—Br5B | 123.0 (7) |
C4A—C5A—Br5A | 118.2 (5) | C4B—C5B—Br5B | 116.4 (5) |
C5A—C6A—N1A | 117.7 (7) | N1B—C6B—C5B | 122.1 (8) |
C5A—C6A—C61A | 127.6 (7) | N1B—C6B—C61B | 116.3 (7) |
N1A—C6A—C61A | 114.7 (7) | C5B—C6B—C61B | 121.7 (8) |
C6A—C61A—H61A | 109.5 | C6B—C61B—H61D | 109.5 |
C6A—C61A—H61B | 109.5 | C6B—C61B—H61E | 109.5 |
H61A—C61A—H61B | 109.5 | H61D—C61B—H61E | 109.5 |
C6A—C61A—H61C | 109.5 | C6B—C61B—H61F | 109.5 |
H61A—C61A—H61C | 109.5 | H61D—C61B—H61F | 109.5 |
H61B—C61A—H61C | 109.5 | H61E—C61B—H61F | 109.5 |
C6A—N1A—C2A—N2A | 179.8 (8) | C6B—N1B—C2B—N2B | 177.7 (7) |
C6A—N1A—C2A—N3A | 1.9 (12) | C6B—N1B—C2B—N3B | −1.1 (11) |
N2A—C2A—N3A—C4A | −179.7 (8) | N1B—C2B—N3B—C4B | −1.4 (11) |
N1A—C2A—N3A—C4A | −1.8 (12) | N2B—C2B—N3B—C4B | 179.8 (7) |
C2A—N3A—C4A—O4A | −179.2 (7) | C2B—N3B—C4B—O4B | −178.2 (7) |
C2A—N3A—C4A—C5A | 0.9 (11) | C2B—N3B—C4B—C5B | 3.5 (11) |
O4A—C4A—C5A—C6A | 179.8 (8) | O4B—C4B—C5B—C6B | 178.5 (8) |
N3A—C4A—C5A—C6A | −0.4 (12) | N3B—C4B—C5B—C6B | −3.3 (11) |
O4A—C4A—C5A—Br5A | −1.6 (11) | O4B—C4B—C5B—Br5B | −0.9 (11) |
N3A—C4A—C5A—Br5A | 178.3 (6) | N3B—C4B—C5B—Br5B | 177.3 (5) |
C4A—C5A—C6A—N1A | 0.5 (12) | C2B—N1B—C6B—C5B | 1.2 (12) |
Br5A—C5A—C6A—N1A | −178.1 (6) | C2B—N1B—C6B—C61B | −179.2 (7) |
C4A—C5A—C6A—C61A | 178.1 (8) | C4B—C5B—C6B—N1B | 1.1 (13) |
Br5A—C5A—C6A—C61A | −0.5 (12) | Br5B—C5B—C6B—N1B | −179.5 (6) |
C2A—N1A—C6A—C5A | −1.2 (12) | C4B—C5B—C6B—C61B | −178.5 (8) |
C2A—N1A—C6A—C61A | −179.1 (8) | Br5B—C5B—C6B—C61B | 1.0 (12) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O4Bi | 0.88 (2) | 1.92 (4) | 2.765 (8) | 160 (9) |
N1A—H1A···Br5Bi | 0.88 (2) | 3.03 (9) | 3.525 (7) | 118 (7) |
N2A—H2A1···O4B | 0.87 (2) | 2.04 (4) | 2.871 (9) | 160 (10) |
N2A—H2A2···O4Aii | 0.88 (2) | 2.05 (6) | 2.807 (8) | 144 (9) |
N2B—H2B1···Br5Aiii | 0.89 (2) | 3.00 (1) | 3.852 (6) | 160 (2) |
N2B—H2B2···O4A | 0.89 (2) | 1.94 (2) | 2.831 (10) | 176 (9) |
N3B—H3B···N3A | 0.87 (2) | 2.03 (3) | 2.883 (10) | 164 (9) |
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. |
2C5H6BrN3O·C5H9NO | F(000) = 1016 |
Mr = 507.21 | Dx = 1.780 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 11.7075 (14) Å | Cell parameters from 7488 reflections |
b = 14.0308 (11) Å | θ = 3.4–26.0° |
c = 11.8308 (14) Å | µ = 4.32 mm−1 |
β = 103.096 (10)° | T = 173 K |
V = 1892.8 (4) Å3 | Block, colourless |
Z = 4 | 0.30 × 0.20 × 0.18 mm |
Stoe IPDSII two-circle diffractometer | 2736 reflections with I > 2σ(I) |
Radiation source: Genix 3D IµS microfocus X-ray source | Rint = 0.113 |
ω scans | θmax = 25.7°, θmin = 3.4° |
Absorption correction: multi-scan X-AREA (Stoe & Cie, 2001) | h = −14→14 |
Tmin = 0.350, Tmax = 0.525 | k = −16→16 |
10611 measured reflections | l = −13→14 |
3544 independent reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.054 | Hydrogen site location: mixed |
wR(F2) = 0.145 | H 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 parameters | Δρmax = 0.77 e Å−3 |
6 restraints | Δρmin = −0.76 e Å−3 |
2C5H6BrN3O·C5H9NO | V = 1892.8 (4) Å3 |
Mr = 507.21 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 11.7075 (14) Å | µ = 4.32 mm−1 |
b = 14.0308 (11) Å | T = 173 K |
c = 11.8308 (14) Å | 0.30 × 0.20 × 0.18 mm |
β = 103.096 (10)° |
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 = 0.525 | Rint = 0.113 |
10611 measured reflections |
R[F2 > 2σ(F2)] = 0.054 | 6 restraints |
wR(F2) = 0.145 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | Δρmax = 0.77 e Å−3 |
3544 reflections | Δρmin = −0.76 e Å−3 |
265 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
N1A | 0.3491 (4) | 0.3717 (3) | 0.4327 (4) | 0.0263 (9) | |
H1A | 0.319 (4) | 0.365 (4) | 0.493 (3) | 0.032* | |
C2A | 0.3699 (4) | 0.4617 (4) | 0.4005 (4) | 0.0259 (10) | |
N2A | 0.3510 (4) | 0.5313 (3) | 0.4707 (4) | 0.0313 (10) | |
H21A | 0.337 (5) | 0.509 (4) | 0.535 (3) | 0.038* | |
H22A | 0.361 (5) | 0.5922 (14) | 0.457 (6) | 0.038* | |
N3A | 0.4043 (4) | 0.4821 (3) | 0.3052 (4) | 0.0283 (9) | |
C4A | 0.4219 (4) | 0.4090 (4) | 0.2328 (4) | 0.0285 (11) | |
O4A | 0.4562 (4) | 0.4274 (3) | 0.1431 (3) | 0.0376 (9) | |
C5A | 0.3990 (4) | 0.3132 (4) | 0.2654 (4) | 0.0279 (10) | |
Br5A | 0.42174 (5) | 0.21464 (4) | 0.16649 (5) | 0.0404 (2) | |
C6A | 0.3644 (4) | 0.2947 (4) | 0.3641 (5) | 0.0266 (11) | |
C61A | 0.3440 (5) | 0.1991 (4) | 0.4112 (5) | 0.0316 (11) | |
H61A | 0.3141 | 0.1552 | 0.3468 | 0.047* | |
H61B | 0.2865 | 0.2048 | 0.4595 | 0.047* | |
H61C | 0.4180 | 0.1745 | 0.4582 | 0.047* | |
N1B | 0.4629 (4) | 0.7805 (3) | 0.0949 (4) | 0.0300 (9) | |
C2B | 0.4586 (4) | 0.6934 (4) | 0.1339 (4) | 0.0284 (11) | |
N2B | 0.4706 (4) | 0.6193 (4) | 0.0674 (4) | 0.0342 (10) | |
H21B | 0.477 (5) | 0.626 (5) | −0.004 (2) | 0.041* | |
H22B | 0.473 (6) | 0.5607 (19) | 0.094 (6) | 0.041* | |
N3B | 0.4399 (4) | 0.6735 (3) | 0.2403 (3) | 0.0259 (9) | |
H3B | 0.434 (5) | 0.6126 (13) | 0.254 (5) | 0.031* | |
C4B | 0.4228 (4) | 0.7424 (4) | 0.3187 (4) | 0.0262 (10) | |
O4B | 0.4063 (3) | 0.7201 (3) | 0.4155 (3) | 0.0306 (8) | |
C5B | 0.4275 (4) | 0.8372 (4) | 0.2757 (4) | 0.0265 (10) | |
Br5B | 0.40471 (5) | 0.93712 (4) | 0.37292 (5) | 0.0385 (2) | |
C6B | 0.4470 (4) | 0.8528 (4) | 0.1661 (5) | 0.0311 (11) | |
C61B | 0.4519 (6) | 0.9497 (4) | 0.1177 (5) | 0.0403 (13) | |
H61D | 0.5272 | 0.9794 | 0.1534 | 0.060* | |
H61E | 0.3879 | 0.9884 | 0.1342 | 0.060* | |
H61F | 0.4439 | 0.9455 | 0.0336 | 0.060* | |
N1X | 0.2378 (4) | 0.3841 (3) | 0.8124 (4) | 0.0329 (10) | |
C11X | 0.2429 (6) | 0.4830 (5) | 0.8452 (6) | 0.0448 (14) | |
H11A | 0.2830 | 0.5193 | 0.7949 | 0.067* | |
H11B | 0.2860 | 0.4895 | 0.9261 | 0.067* | |
H11C | 0.1631 | 0.5077 | 0.8370 | 0.067* | |
C2X | 0.2593 (4) | 0.3522 (4) | 0.7141 (5) | 0.0314 (11) | |
O2X | 0.2856 (4) | 0.4009 (3) | 0.6376 (3) | 0.0397 (9) | |
C3X | 0.2452 (5) | 0.2454 (4) | 0.7119 (5) | 0.0359 (12) | |
H3X1 | 0.3167 | 0.2141 | 0.6983 | 0.043* | |
H3X2 | 0.1776 | 0.2262 | 0.6495 | 0.043* | |
C4X | 0.2248 (5) | 0.2179 (4) | 0.8297 (5) | 0.0391 (13) | |
H4X1 | 0.2939 | 0.1841 | 0.8762 | 0.047* | |
H4X2 | 0.1552 | 0.1762 | 0.8211 | 0.047* | |
C5X | 0.2049 (5) | 0.3134 (5) | 0.8881 (5) | 0.0390 (13) | |
H5X1 | 0.1218 | 0.3207 | 0.8921 | 0.047* | |
H5X2 | 0.2551 | 0.3178 | 0.9674 | 0.047* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1A | 0.031 (2) | 0.027 (2) | 0.022 (2) | 0.0008 (17) | 0.0095 (16) | −0.0001 (16) |
C2A | 0.025 (2) | 0.022 (3) | 0.029 (2) | 0.0012 (18) | 0.0046 (18) | 0.0028 (19) |
N2A | 0.051 (3) | 0.026 (2) | 0.021 (2) | −0.002 (2) | 0.0175 (19) | −0.0013 (17) |
N3A | 0.035 (2) | 0.025 (2) | 0.026 (2) | −0.0021 (18) | 0.0091 (17) | 0.0010 (17) |
C4A | 0.034 (2) | 0.029 (3) | 0.022 (2) | 0.001 (2) | 0.0063 (19) | −0.005 (2) |
O4A | 0.058 (2) | 0.033 (2) | 0.0282 (19) | −0.0012 (18) | 0.0223 (17) | −0.0012 (16) |
C5A | 0.028 (2) | 0.029 (3) | 0.025 (2) | 0.002 (2) | 0.0022 (19) | −0.001 (2) |
Br5A | 0.0498 (3) | 0.0357 (3) | 0.0353 (3) | 0.0039 (2) | 0.0092 (2) | −0.0080 (2) |
C6A | 0.022 (2) | 0.024 (3) | 0.031 (3) | 0.0005 (18) | −0.0003 (19) | −0.002 (2) |
C61A | 0.035 (3) | 0.029 (3) | 0.031 (3) | 0.000 (2) | 0.009 (2) | −0.001 (2) |
N1B | 0.034 (2) | 0.033 (2) | 0.024 (2) | −0.0006 (18) | 0.0088 (17) | 0.0010 (18) |
C2B | 0.030 (2) | 0.032 (3) | 0.022 (2) | 0.000 (2) | 0.0054 (19) | 0.002 (2) |
N2B | 0.049 (3) | 0.033 (3) | 0.024 (2) | 0.005 (2) | 0.016 (2) | 0.0011 (18) |
N3B | 0.036 (2) | 0.025 (2) | 0.0174 (19) | −0.0021 (18) | 0.0068 (16) | 0.0009 (16) |
C4B | 0.026 (2) | 0.025 (3) | 0.027 (3) | 0.0004 (19) | 0.0040 (19) | −0.003 (2) |
O4B | 0.045 (2) | 0.029 (2) | 0.0204 (17) | −0.0012 (16) | 0.0120 (15) | 0.0034 (14) |
C5B | 0.029 (2) | 0.027 (3) | 0.024 (2) | 0.003 (2) | 0.0083 (18) | 0.001 (2) |
Br5B | 0.0531 (3) | 0.0284 (3) | 0.0349 (3) | 0.0024 (2) | 0.0122 (2) | −0.0022 (2) |
C6B | 0.030 (2) | 0.031 (3) | 0.033 (3) | −0.003 (2) | 0.008 (2) | 0.002 (2) |
C61B | 0.059 (3) | 0.032 (3) | 0.033 (3) | −0.004 (3) | 0.017 (3) | 0.005 (2) |
N1X | 0.039 (2) | 0.039 (3) | 0.025 (2) | −0.007 (2) | 0.0152 (18) | 0.0029 (19) |
C11X | 0.051 (3) | 0.045 (4) | 0.040 (3) | −0.002 (3) | 0.013 (3) | −0.004 (3) |
C2X | 0.027 (2) | 0.038 (3) | 0.029 (3) | 0.001 (2) | 0.006 (2) | 0.004 (2) |
O2X | 0.056 (2) | 0.038 (2) | 0.031 (2) | −0.0020 (19) | 0.0205 (17) | 0.0044 (17) |
C3X | 0.041 (3) | 0.034 (3) | 0.034 (3) | −0.003 (2) | 0.011 (2) | −0.006 (2) |
C4X | 0.043 (3) | 0.036 (3) | 0.037 (3) | −0.004 (2) | 0.008 (2) | 0.009 (2) |
C5X | 0.049 (3) | 0.051 (4) | 0.022 (3) | −0.005 (3) | 0.017 (2) | 0.007 (2) |
N1A—C2A | 1.356 (7) | C4B—O4B | 1.243 (7) |
N1A—C6A | 1.387 (7) | C4B—C5B | 1.429 (7) |
N1A—H1A | 0.876 (10) | C5B—C6B | 1.384 (7) |
C2A—N3A | 1.312 (7) | C5B—Br5B | 1.871 (5) |
C2A—N2A | 1.332 (7) | C6B—C61B | 1.482 (8) |
N2A—H21A | 0.876 (10) | C61B—H61D | 0.9800 |
N2A—H22A | 0.881 (10) | C61B—H61E | 0.9800 |
N3A—C4A | 1.381 (7) | C61B—H61F | 0.9800 |
C4A—O4A | 1.244 (7) | N1X—C2X | 1.322 (7) |
C4A—C5A | 1.440 (8) | N1X—C11X | 1.439 (8) |
C5A—C6A | 1.345 (8) | N1X—C5X | 1.446 (7) |
C5A—Br5A | 1.869 (5) | C11X—H11A | 0.9800 |
C6A—C61A | 1.493 (7) | C11X—H11B | 0.9800 |
C61A—H61A | 0.9800 | C11X—H11C | 0.9800 |
C61A—H61B | 0.9800 | C2X—O2X | 1.228 (7) |
C61A—H61C | 0.9800 | C2X—C3X | 1.508 (8) |
N1B—C2B | 1.312 (7) | C3X—C4X | 1.516 (8) |
N1B—C6B | 1.357 (7) | C3X—H3X1 | 0.9900 |
C2B—N2B | 1.330 (7) | C3X—H3X2 | 0.9900 |
C2B—N3B | 1.354 (7) | C4X—C5X | 1.548 (9) |
N2B—H21B | 0.875 (10) | C4X—H4X1 | 0.9900 |
N2B—H22B | 0.878 (10) | C4X—H4X2 | 0.9900 |
N3B—C4B | 1.386 (7) | C5X—H5X1 | 0.9900 |
N3B—H3B | 0.876 (10) | C5X—H5X2 | 0.9900 |
C2A—N1A—C6A | 120.4 (4) | C4B—C5B—Br5B | 117.1 (4) |
C2A—N1A—H1A | 118 (4) | N1B—C6B—C5B | 122.5 (5) |
C6A—N1A—H1A | 122 (4) | N1B—C6B—C61B | 115.1 (5) |
N3A—C2A—N2A | 120.1 (5) | C5B—C6B—C61B | 122.4 (5) |
N3A—C2A—N1A | 123.6 (5) | C6B—C61B—H61D | 109.5 |
N2A—C2A—N1A | 116.2 (5) | C6B—C61B—H61E | 109.5 |
C2A—N2A—H21A | 112 (4) | H61D—C61B—H61E | 109.5 |
C2A—N2A—H22A | 124 (5) | C6B—C61B—H61F | 109.5 |
H21A—N2A—H22A | 124 (6) | H61D—C61B—H61F | 109.5 |
C2A—N3A—C4A | 119.3 (5) | H61E—C61B—H61F | 109.5 |
O4A—C4A—N3A | 119.8 (5) | C2X—N1X—C11X | 124.0 (5) |
O4A—C4A—C5A | 122.5 (5) | C2X—N1X—C5X | 116.3 (5) |
N3A—C4A—C5A | 117.7 (5) | C11X—N1X—C5X | 119.7 (5) |
C6A—C5A—C4A | 121.5 (5) | N1X—C11X—H11A | 109.5 |
C6A—C5A—Br5A | 121.0 (4) | N1X—C11X—H11B | 109.5 |
C4A—C5A—Br5A | 117.5 (4) | H11A—C11X—H11B | 109.5 |
C5A—C6A—N1A | 117.5 (5) | N1X—C11X—H11C | 109.5 |
C5A—C6A—C61A | 127.1 (5) | H11A—C11X—H11C | 109.5 |
N1A—C6A—C61A | 115.4 (5) | H11B—C11X—H11C | 109.5 |
C6A—C61A—H61A | 109.5 | O2X—C2X—N1X | 126.2 (5) |
C6A—C61A—H61B | 109.5 | O2X—C2X—C3X | 125.8 (5) |
H61A—C61A—H61B | 109.5 | N1X—C2X—C3X | 108.0 (5) |
C6A—C61A—H61C | 109.5 | C2X—C3X—C4X | 106.0 (5) |
H61A—C61A—H61C | 109.5 | C2X—C3X—H3X1 | 110.5 |
H61B—C61A—H61C | 109.5 | C4X—C3X—H3X1 | 110.5 |
C2B—N1B—C6B | 117.2 (5) | C2X—C3X—H3X2 | 110.5 |
N1B—C2B—N2B | 120.2 (5) | C4X—C3X—H3X2 | 110.5 |
N1B—C2B—N3B | 123.1 (5) | H3X1—C3X—H3X2 | 108.7 |
N2B—C2B—N3B | 116.7 (5) | C3X—C4X—C5X | 105.1 (5) |
C2B—N2B—H21B | 122 (5) | C3X—C4X—H4X1 | 110.7 |
C2B—N2B—H22B | 121 (5) | C5X—C4X—H4X1 | 110.7 |
H21B—N2B—H22B | 117 (6) | C3X—C4X—H4X2 | 110.7 |
C2B—N3B—C4B | 123.8 (5) | C5X—C4X—H4X2 | 110.7 |
C2B—N3B—H3B | 114 (4) | H4X1—C4X—H4X2 | 108.8 |
C4B—N3B—H3B | 122 (4) | N1X—C5X—C4X | 103.3 (4) |
O4B—C4B—N3B | 121.1 (5) | N1X—C5X—H5X1 | 111.1 |
O4B—C4B—C5B | 126.1 (5) | C4X—C5X—H5X1 | 111.1 |
N3B—C4B—C5B | 112.8 (5) | N1X—C5X—H5X2 | 111.1 |
C6B—C5B—C4B | 120.6 (5) | C4X—C5X—H5X2 | 111.1 |
C6B—C5B—Br5B | 122.3 (4) | H5X1—C5X—H5X2 | 109.1 |
C6A—N1A—C2A—N3A | 0.3 (7) | C2B—N3B—C4B—C5B | −0.3 (6) |
C6A—N1A—C2A—N2A | 178.9 (4) | O4B—C4B—C5B—C6B | 179.7 (5) |
N2A—C2A—N3A—C4A | −179.1 (4) | N3B—C4B—C5B—C6B | 0.2 (6) |
N1A—C2A—N3A—C4A | −0.6 (7) | O4B—C4B—C5B—Br5B | −0.9 (7) |
C2A—N3A—C4A—O4A | −178.9 (5) | N3B—C4B—C5B—Br5B | 179.6 (3) |
C2A—N3A—C4A—C5A | 1.2 (6) | C2B—N1B—C6B—C5B | 0.3 (7) |
O4A—C4A—C5A—C6A | 178.5 (5) | C2B—N1B—C6B—C61B | −179.7 (5) |
N3A—C4A—C5A—C6A | −1.6 (7) | C4B—C5B—C6B—N1B | −0.2 (7) |
O4A—C4A—C5A—Br5A | −0.3 (7) | Br5B—C5B—C6B—N1B | −179.6 (4) |
N3A—C4A—C5A—Br5A | 179.5 (3) | C4B—C5B—C6B—C61B | 179.7 (5) |
C4A—C5A—C6A—N1A | 1.3 (7) | Br5B—C5B—C6B—C61B | 0.3 (7) |
Br5A—C5A—C6A—N1A | −179.9 (3) | C11X—N1X—C2X—O2X | −0.5 (8) |
C4A—C5A—C6A—C61A | −176.4 (5) | C5X—N1X—C2X—O2X | 178.1 (5) |
Br5A—C5A—C6A—C61A | 2.4 (7) | C11X—N1X—C2X—C3X | 180.0 (5) |
C2A—N1A—C6A—C5A | −0.7 (6) | C5X—N1X—C2X—C3X | −1.4 (6) |
C2A—N1A—C6A—C61A | 177.4 (4) | O2X—C2X—C3X—C4X | 174.5 (5) |
C6B—N1B—C2B—N2B | 178.3 (4) | N1X—C2X—C3X—C4X | −6.0 (6) |
C6B—N1B—C2B—N3B | −0.3 (7) | C2X—C3X—C4X—C5X | 10.3 (6) |
N1B—C2B—N3B—C4B | 0.3 (7) | C2X—N1X—C5X—C4X | 7.9 (6) |
N2B—C2B—N3B—C4B | −178.4 (4) | C11X—N1X—C5X—C4X | −173.4 (5) |
C2B—N3B—C4B—O4B | −179.8 (5) | C3X—C4X—C5X—N1X | −10.8 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O2X | 0.88 (1) | 1.90 (3) | 2.723 (6) | 155 (6) |
N2A—H21A···O2X | 0.88 (1) | 2.11 (3) | 2.919 (6) | 153 (6) |
N2A—H22A···O4B | 0.88 (1) | 1.97 (2) | 2.839 (6) | 170 (6) |
N2B—H21B···O4Ai | 0.88 (1) | 2.11 (4) | 2.887 (6) | 147 (6) |
N2B—H22B···O4A | 0.88 (1) | 1.98 (2) | 2.855 (6) | 172 (6) |
N3B—H3B···N3A | 0.88 (1) | 1.98 (2) | 2.850 (6) | 170 (6) |
Symmetry code: (i) −x+1, −y+1, −z. |
C4.64H5.27Br0.64Cl0.37N3O·C5H6BrN3O | F(000) = 762 |
Mr = 386.58 | Dx = 1.953 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 9.270 (5) Å | Cell parameters from 1316 reflections |
b = 11.423 (4) Å | θ = 4.4–25.8° |
c = 12.559 (7) Å | µ = 5.13 mm−1 |
β = 98.61 (4)° | T = 173 K |
V = 1314.9 (11) Å3 | Block, colourless |
Z = 4 | 0.29 × 0.22 × 0.20 mm |
Stoe IPDSII two-circle diffractometer | 2241 reflections with I > 2σ(I) |
Radiation source: Genix 3D IµS microfocus X-ray source | Rint = 0.086 |
ω scans | θmax = 25.9°, θmin = 3.3° |
Absorption correction: multi-scan X-AREA (Stoe & Cie, 2001) | h = −11→9 |
Tmin = 0.310, Tmax = 0.435 | k = −13→13 |
7577 measured reflections | l = −15→15 |
2517 independent reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.093 | Hydrogen site location: mixed |
wR(F2) = 0.202 | H 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 parameters | Δρmax = 0.55 e Å−3 |
9 restraints | Δρmin = −1.13 e Å−3 |
C4.64H5.27Br0.64Cl0.37N3O·C5H6BrN3O | V = 1314.9 (11) Å3 |
Mr = 386.58 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 9.270 (5) Å | µ = 5.13 mm−1 |
b = 11.423 (4) Å | T = 173 K |
c = 12.559 (7) Å | 0.29 × 0.22 × 0.20 mm |
β = 98.61 (4)° |
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 = 0.435 | Rint = 0.086 |
7577 measured reflections |
R[F2 > 2σ(F2)] = 0.093 | 9 restraints |
wR(F2) = 0.202 | H 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 | Δρmax = 0.55 e Å−3 |
206 parameters | Δρmin = −1.13 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
N1A | 0.2550 (8) | 0.1571 (7) | 0.3913 (6) | 0.0347 (17) | |
H1A | 0.181 (7) | 0.140 (5) | 0.342 (4) | 0.042* | |
C2A | 0.3287 (11) | 0.2569 (9) | 0.3750 (8) | 0.042 (2) | |
N2A | 0.2840 (9) | 0.3198 (8) | 0.2871 (7) | 0.0403 (19) | |
H2A1 | 0.318 (11) | 0.391 (4) | 0.283 (9) | 0.048* | |
H2A2 | 0.197 (5) | 0.293 (9) | 0.262 (8) | 0.048* | |
N3A | 0.4456 (8) | 0.2911 (7) | 0.4432 (6) | 0.0345 (17) | |
C4A | 0.4908 (10) | 0.2266 (8) | 0.5322 (8) | 0.038 (2) | |
O4A | 0.6055 (7) | 0.2560 (6) | 0.5926 (5) | 0.0395 (16) | |
C5A | 0.4105 (11) | 0.1243 (9) | 0.5528 (8) | 0.038 (2) | |
Br5A | 0.46972 (13) | 0.03390 (12) | 0.67526 (10) | 0.0596 (4) | |
C6A | 0.2934 (10) | 0.0890 (9) | 0.4817 (8) | 0.039 (2) | |
C61A | 0.2038 (12) | −0.0148 (10) | 0.4914 (10) | 0.051 (3) | |
H61A | 0.1270 | −0.0198 | 0.4289 | 0.076* | |
H61B | 0.1593 | −0.0092 | 0.5573 | 0.076* | |
H61C | 0.2651 | −0.0850 | 0.4947 | 0.076* | |
N1B | 0.8520 (9) | 0.5851 (7) | 0.4223 (7) | 0.0384 (18) | |
C2B | 0.7625 (11) | 0.5008 (9) | 0.4461 (8) | 0.041 (2) | |
N2B | 0.8076 (11) | 0.4262 (8) | 0.5297 (8) | 0.051 (2) | |
H2B1 | 0.903 (2) | 0.423 (11) | 0.545 (10) | 0.062* | |
H2B2 | 0.752 (11) | 0.366 (7) | 0.539 (10) | 0.062* | |
N3B | 0.6243 (9) | 0.4849 (7) | 0.3897 (7) | 0.0387 (19) | |
H3B | 0.557 (8) | 0.436 (7) | 0.405 (8) | 0.046* | |
C4B | 0.5682 (10) | 0.5539 (8) | 0.3050 (8) | 0.036 (2) | |
O4B | 0.4456 (8) | 0.5313 (6) | 0.2556 (6) | 0.0443 (17) | |
C6B | 0.7984 (10) | 0.6560 (8) | 0.3389 (8) | 0.039 (2) | |
C5B | 0.6645 (11) | 0.6431 (9) | 0.2799 (8) | 0.042 (2) | |
H5B | 0.6332 | 0.6931 | 0.2173 | 0.050* | 0.365 (5) |
Cl6B | 0.9109 (11) | 0.7634 (9) | 0.3097 (10) | 0.044 (2) | 0.365 (5) |
Br5B | 0.60463 (19) | 0.73940 (14) | 0.15832 (14) | 0.0444 (6) | 0.635 (5) |
C61B | 0.89989 (19) | 0.74996 (14) | 0.33160 (14) | 0.042 (9) | 0.635 (5) |
H61D | 0.9880 | 0.7371 | 0.3840 | 0.064* | 0.635 (5) |
H61E | 0.8549 | 0.8245 | 0.3471 | 0.064* | 0.635 (5) |
H61F | 0.9259 | 0.7522 | 0.2588 | 0.064* | 0.635 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1A | 0.031 (4) | 0.031 (4) | 0.040 (4) | −0.005 (3) | −0.001 (3) | −0.003 (3) |
C2A | 0.039 (5) | 0.040 (5) | 0.045 (5) | 0.001 (4) | −0.002 (4) | −0.007 (5) |
N2A | 0.039 (5) | 0.038 (5) | 0.039 (4) | 0.004 (4) | −0.010 (4) | 0.001 (4) |
N3A | 0.033 (4) | 0.028 (4) | 0.038 (4) | 0.004 (3) | −0.007 (3) | −0.002 (3) |
C4A | 0.028 (5) | 0.032 (5) | 0.052 (6) | −0.009 (4) | 0.005 (4) | −0.005 (4) |
O4A | 0.036 (4) | 0.038 (4) | 0.039 (4) | −0.005 (3) | −0.009 (3) | −0.001 (3) |
C5A | 0.043 (5) | 0.036 (5) | 0.035 (5) | 0.001 (4) | 0.001 (4) | 0.007 (4) |
Br5A | 0.0529 (7) | 0.0667 (8) | 0.0558 (7) | −0.0105 (6) | −0.0027 (5) | 0.0191 (6) |
C6A | 0.028 (5) | 0.036 (5) | 0.053 (6) | −0.002 (4) | 0.003 (4) | −0.001 (5) |
C61A | 0.043 (6) | 0.047 (6) | 0.062 (7) | −0.013 (5) | 0.004 (5) | 0.008 (6) |
N1B | 0.038 (4) | 0.037 (4) | 0.041 (4) | −0.005 (4) | 0.006 (4) | 0.006 (4) |
C2B | 0.033 (5) | 0.045 (6) | 0.041 (5) | −0.002 (4) | −0.001 (4) | −0.001 (5) |
N2B | 0.064 (6) | 0.035 (5) | 0.051 (5) | −0.012 (5) | −0.004 (5) | 0.018 (4) |
N3B | 0.035 (4) | 0.034 (4) | 0.046 (5) | −0.007 (3) | −0.001 (4) | −0.001 (4) |
C4B | 0.033 (5) | 0.034 (5) | 0.039 (5) | 0.002 (4) | 0.004 (4) | −0.005 (4) |
O4B | 0.045 (4) | 0.031 (4) | 0.054 (4) | 0.004 (3) | −0.002 (3) | 0.006 (3) |
C6B | 0.038 (5) | 0.034 (5) | 0.048 (6) | −0.001 (4) | 0.012 (4) | 0.000 (4) |
C5B | 0.046 (6) | 0.040 (5) | 0.038 (5) | 0.008 (5) | 0.003 (4) | 0.002 (4) |
Cl6B | 0.048 (5) | 0.042 (5) | 0.044 (4) | −0.015 (4) | 0.014 (4) | 0.015 (4) |
Br5B | 0.0484 (10) | 0.0365 (9) | 0.0478 (10) | 0.0031 (7) | 0.0060 (7) | 0.0066 (7) |
C61B | 0.039 (12) | 0.037 (12) | 0.055 (16) | 0.004 (9) | 0.022 (9) | 0.036 (9) |
N1A—C2A | 1.360 (12) | N1B—C6B | 1.358 (13) |
N1A—C6A | 1.378 (12) | C2B—N2B | 1.368 (13) |
N1A—H1A | 0.879 (9) | C2B—N3B | 1.380 (12) |
C2A—N2A | 1.330 (13) | N2B—H2B1 | 0.882 (11) |
C2A—N3A | 1.335 (12) | N2B—H2B2 | 0.881 (10) |
N2A—H2A1 | 0.878 (10) | N3B—C4B | 1.363 (13) |
N2A—H2A2 | 0.879 (10) | N3B—H3B | 0.880 (10) |
N3A—C4A | 1.352 (12) | C4B—O4B | 1.238 (11) |
C4A—O4A | 1.256 (11) | C4B—C5B | 1.421 (14) |
C4A—C5A | 1.429 (13) | C6B—C5B | 1.355 (14) |
C5A—C6A | 1.360 (13) | C6B—C61B | 1.439 (9) |
C5A—Br5A | 1.865 (9) | C6B—Cl6B | 1.686 (15) |
C6A—C61A | 1.464 (14) | C5B—Br5B | 1.896 (10) |
C61A—H61A | 0.9800 | C5B—H5B | 0.9799 |
C61A—H61B | 0.9800 | C61B—H61D | 0.9800 |
C61A—H61C | 0.9800 | C61B—H61E | 0.9800 |
N1B—C2B | 1.335 (13) | C61B—H61F | 0.9800 |
C2A—N1A—C6A | 121.5 (8) | N1B—C2B—N3B | 122.7 (9) |
C2A—N1A—H1A | 116.4 (19) | N2B—C2B—N3B | 117.8 (9) |
C6A—N1A—H1A | 122.1 (19) | C2B—N2B—H2B1 | 112 (8) |
N2A—C2A—N3A | 119.8 (9) | C2B—N2B—H2B2 | 118 (8) |
N2A—C2A—N1A | 118.5 (9) | H2B1—N2B—H2B2 | 122 (10) |
N3A—C2A—N1A | 121.8 (9) | C4B—N3B—C2B | 122.7 (8) |
C2A—N2A—H2A1 | 119 (8) | C4B—N3B—H3B | 110 (7) |
C2A—N2A—H2A2 | 105 (7) | C2B—N3B—H3B | 127 (7) |
H2A1—N2A—H2A2 | 128 (10) | O4B—C4B—N3B | 119.0 (9) |
C2A—N3A—C4A | 119.5 (8) | O4B—C4B—C5B | 126.8 (9) |
O4A—C4A—N3A | 118.9 (8) | N3B—C4B—C5B | 114.1 (8) |
O4A—C4A—C5A | 121.7 (9) | C5B—C6B—N1B | 123.8 (9) |
N3A—C4A—C5A | 119.3 (9) | C5B—C6B—C61B | 126.9 (9) |
C6A—C5A—C4A | 120.6 (9) | N1B—C6B—C61B | 109.0 (8) |
C6A—C5A—Br5A | 119.0 (8) | C5B—C6B—Cl6B | 120.4 (9) |
C4A—C5A—Br5A | 120.3 (7) | N1B—C6B—Cl6B | 115.8 (8) |
C5A—C6A—N1A | 117.2 (9) | C6B—C5B—C4B | 120.8 (9) |
C5A—C6A—C61A | 126.3 (10) | C6B—C5B—Br5B | 120.7 (8) |
N1A—C6A—C61A | 116.5 (8) | C4B—C5B—Br5B | 118.5 (7) |
C6A—C61A—H61A | 109.5 | C6B—C5B—H5B | 120.8 |
C6A—C61A—H61B | 109.5 | C4B—C5B—H5B | 118.4 |
H61A—C61A—H61B | 109.5 | C6B—C61B—H61D | 109.5 |
C6A—C61A—H61C | 109.5 | C6B—C61B—H61E | 109.5 |
H61A—C61A—H61C | 109.5 | H61D—C61B—H61E | 109.5 |
H61B—C61A—H61C | 109.5 | C6B—C61B—H61F | 109.5 |
C2B—N1B—C6B | 115.8 (8) | H61D—C61B—H61F | 109.5 |
N1B—C2B—N2B | 119.5 (9) | H61E—C61B—H61F | 109.5 |
C6A—N1A—C2A—N2A | −178.7 (9) | N1B—C2B—N3B—C4B | 0.1 (16) |
C6A—N1A—C2A—N3A | 2.9 (15) | N2B—C2B—N3B—C4B | 180.0 (9) |
N2A—C2A—N3A—C4A | −179.8 (9) | C2B—N3B—C4B—O4B | 177.1 (9) |
N1A—C2A—N3A—C4A | −1.3 (14) | C2B—N3B—C4B—C5B | 0.2 (13) |
C2A—N3A—C4A—O4A | 176.2 (9) | C2B—N1B—C6B—C5B | −1.6 (15) |
C2A—N3A—C4A—C5A | −1.4 (14) | C2B—N1B—C6B—C61B | 173.2 (8) |
O4A—C4A—C5A—C6A | −174.7 (10) | C2B—N1B—C6B—Cl6B | 179.4 (8) |
N3A—C4A—C5A—C6A | 2.8 (15) | N1B—C6B—C5B—C4B | 1.9 (15) |
O4A—C4A—C5A—Br5A | 2.8 (14) | C61B—C6B—C5B—C4B | −171.9 (8) |
N3A—C4A—C5A—Br5A | −179.7 (7) | Cl6B—C6B—C5B—C4B | −179.1 (9) |
C4A—C5A—C6A—N1A | −1.3 (15) | N1B—C6B—C5B—Br5B | −175.3 (8) |
Br5A—C5A—C6A—N1A | −178.8 (7) | C61B—C6B—C5B—Br5B | 10.8 (14) |
C4A—C5A—C6A—C61A | 178.5 (10) | Cl6B—C6B—C5B—Br5B | 3.6 (13) |
Br5A—C5A—C6A—C61A | 1.0 (15) | O4B—C4B—C5B—C6B | −177.8 (10) |
C2A—N1A—C6A—C5A | −1.5 (14) | N3B—C4B—C5B—C6B | −1.1 (14) |
C2A—N1A—C6A—C61A | 178.7 (9) | O4B—C4B—C5B—Br5B | −0.4 (14) |
C6B—N1B—C2B—N2B | −179.4 (9) | N3B—C4B—C5B—Br5B | 176.2 (7) |
C6B—N1B—C2B—N3B | 0.6 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O4Bi | 0.88 (1) | 1.99 (3) | 2.810 (10) | 154 (7) |
N1A—H1A···Br5Bi | 0.88 (1) | 2.88 (9) | 3.429 (8) | 122 (8) |
N2A—H2A1···O4B | 0.88 (1) | 2.05 (3) | 2.901 (12) | 163 (10) |
N2A—H2A2···O4Aii | 0.88 (1) | 2.24 (8) | 2.872 (11) | 129 (9) |
N2A—H2A2···Br5Aii | 0.88 (1) | 2.97 (10) | 3.469 (8) | 118 (9) |
N2B—H2B1···N1Biii | 0.88 (1) | 2.24 (2) | 3.125 (13) | 178 (12) |
N2B—H2B2···O4A | 0.88 (1) | 2.03 (4) | 2.890 (11) | 164 (11) |
N3B—H3B···N3A | 0.88 (1) | 2.04 (3) | 2.903 (11) | 165 (10) |
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. |
Structure | Compound 1 (mg, mmol) | Compound 2 (mg, mmol) | Solvent (µL) | Temperature (K) |
(Ia) | CIC: 3.4, 0.023 | AHP: 3.3, 0.034 | DMF: 50 | 323 |
(Ib) | CIC: 3.4, 0.023 | AHP: 3.3, 0.034 | DMAC: 50 | 323 |
(II) | BMIC: 4.6, 0.023 | ACMP: 3.5, 0.024 | DMSO: 75 | 323 |
(III) | BMIC: 4.2, 0.021 | NMP: 170 | 277 | |
(IV) | CIC: 3.4, 0.023 | BMIC: 7.0, 0.034 | DMAC: 500 | 296 |
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 formula | C5H7N2+·C4H3ClN3O−·3C4H4ClN3O | 2C5H7N2+·2C4H3ClN3O−·10C4H4ClN3O·C5H6N2 | C5H6BrN3O | 2C5H6BrN3O·C5H9NO |
Mr | 676.32 | 2028.97 | 204.04 | 507.21 |
Crystal system, space group | Triclinic, P1 | Triclinic, P1 | Monoclinic, P21/n | Monoclinic, P21/n |
Temperature (K) | 173 | 173 | 173 | 173 |
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), 90 | 90, 103.096 (10), 90 |
V (Å3) | 1360.7 (3) | 4137.9 (4) | 1332.6 (3) | 1892.8 (4) |
Z | 2 | 2 | 8 | 4 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.50 | 0.49 | 6.10 | 4.32 |
Crystal size (mm) | 0.26 × 0.09 × 0.07 | 0.24 × 0.10 × 0.04 | 0.35 × 0.30 × 0.25 | 0.30 × 0.20 × 0.18 |
Data collection | ||||
Diffractometer | Stoe IPDSII two-circle diffractometer | Stoe IPDSII two-circle diffractometer | Stoe IPDSII two-circle diffractometer | Stoe IPDSII two-circle diffractometer |
Absorption correction | Multi-scan X-AREA (Stoe & Cie, 2001) | Multi-scan X-AREA (Stoe & Cie, 2001) | Multi-scan X-AREA (Stoe & Cie, 2001) | Multi-scan X-AREA (Stoe & Cie, 2001) |
Tmin, Tmax | 0.880, 0.960 | 0.890, 0.980 | 0.220, 0.310 | 0.350, 0.525 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 22097, 5228, 3077 | 20468, 16871, 10620 | 6144, 2480, 1986 | 10611, 3544, 2736 |
Rint | 0.125 | 0.026 | 0.103 | 0.113 |
(sin θ/λ)max (Å−1) | 0.615 | 0.626 | 0.610 | 0.610 |
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 reflections | 5228 | 16871 | 2480 | 3544 |
No. of parameters | 430 | 1350 | 201 | 265 |
No. of restraints | 14 | 313 | 11 | 6 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H 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 Å−3) | 0.42, −0.43 | 1.51, −1.23 | 1.06, −1.50 | 0.77, −0.76 |
(IV) | |
Crystal data | |
Chemical formula | C4.64H5.27Br0.64Cl0.37N3O·C5H6BrN3O |
Mr | 386.58 |
Crystal system, space group | Monoclinic, 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 |
V (Å3) | 1314.9 (11) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 5.13 |
Crystal size (mm) | 0.29 × 0.22 × 0.20 |
Data collection | |
Diffractometer | Stoe IPDSII two-circle diffractometer |
Absorption correction | Multi-scan X-AREA (Stoe & Cie, 2001) |
Tmin, Tmax | 0.310, 0.435 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7577, 2517, 2241 |
Rint | 0.086 |
(sin θ/λ)max (Å−1) | 0.614 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.093, 0.202, 1.19 |
No. of reflections | 2517 |
No. of parameters | 206 |
No. of restraints | 9 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
w = 1/[σ2(Fo2) + 18.9797P] where P = (Fo2 + 2Fc2)/3 | |
Δρmax, Δρmin (e Å−3) | 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).
D—H···A | D—H | H···A | D···A | D—H···A |
N2A—H21A···O4B | 0.885 (19) | 2.08 (2) | 2.960 (4) | 173 (4) |
N2A—H22A···N1C | 0.880 (19) | 2.14 (2) | 3.014 (4) | 172 (4) |
N2B—H21B···N1D | 0.873 (19) | 2.14 (2) | 3.016 (4) | 178 (4) |
N2B—H22B···O4A | 0.897 (19) | 1.92 (2) | 2.820 (4) | 177 (4) |
N3B—H3B···N3A | 0.875 (19) | 2.03 (2) | 2.893 (4) | 167 (4) |
N2C—H21C···N1A | 0.880 (19) | 2.12 (2) | 2.999 (4) | 174 (4) |
N3C—H3C···O4Di | 0.884 (19) | 1.85 (2) | 2.730 (4) | 174 (4) |
N2D—H21D···N1B | 0.888 (19) | 2.06 (2) | 2.936 (4) | 171 (4) |
N3D—H3D···O4Cii | 0.891 (19) | 1.88 (2) | 2.760 (4) | 170 (4) |
N1E—H1E···O4A | 0.890 (19) | 1.70 (2) | 2.554 (4) | 160 (4) |
N2E—H21E···O4Biii | 0.862 (19) | 2.08 (2) | 2.905 (4) | 161 (4) |
N2E—H22E···O4Biv | 0.889 (19) | 2.26 (2) | 3.086 (4) | 155 (3) |
Symmetry codes: (i) x+1, y, z+1; (ii) x−1, y, z−1; (iii) x, y−1, z; (iv) −x+1, −y+1, −z+1. |
Molecule | r.m.s.d. | Molecule | r.m.s.d. | Molecule | r.m.s.d. |
A | 0.0176 | G | 0.0226 | O | 0.0134 |
B | 0.0076 | H | 0.0147 | P | 0.0079 |
C | 0.0191 | I | 0.0104 | R | 0.0384 |
D | 0.0167 | K | 0.0093 | S | 0.0439 |
E | 0.0083 | L | 0.0204 | ||
F | 0.0109 | M | 0.0107 |
D—H···A | D—H | H···A | D···A | D—H···A |
N2A—H2A1···N1Fi | 0.880 (5) | 2.25 (2) | 3.107 (11) | 166 (6) |
N2A—H2A2···O4B | 0.881 (5) | 1.953 (15) | 2.829 (11) | 173 (5) |
N3A—H3A···N3B | 0.880 (5) | 2.03 (3) | 2.900 (11) | 168 (10) |
N2B—H2B1···O4A | 0.880 (5) | 2.091 (15) | 2.960 (11) | 169 (3) |
N2B—H2B2···N1C | 0.880 (5) | 2.28 (2) | 3.140 (11) | 167 (7) |
N2C—H2C1···N1B | 0.880 (5) | 2.09 (4) | 2.936 (11) | 160 (11) |
N3C—H3C···O4D | 0.880 (5) | 1.962 (16) | 2.839 (11) | 175 (11) |
N2D—H2D1···N1E | 0.880 (5) | 2.13 (2) | 2.991 (11) | 167 (6) |
N3D—H3D···O4C | 0.880 (5) | 1.86 (2) | 2.732 (10) | 169 (10) |
C5D—H5D···Cl6Gii | 0.95 | 2.88 | 3.769 (11) | 155.7 |
N2E—H2E1···N1D | 0.880 (5) | 2.048 (16) | 2.917 (11) | 169 (5) |
N3E—H3E···O4F | 0.880 (5) | 1.92 (3) | 2.772 (11) | 164 (11) |
N2F—H2F1···N1Aiii | 0.881 (5) | 2.057 (17) | 2.930 (11) | 171 (6) |
N2F—H2F2···N2R | 0.880 (5) | 2.44 (4) | 3.29 (2) | 162 (9) |
N3F—H3F···O4E | 0.880 (5) | 1.90 (3) | 2.761 (11) | 166 (10) |
N2G—H2G1···O4H | 0.880 (5) | 2.03 (3) | 2.892 (11) | 166 (10) |
N2G—H2G2···N1Miv | 0.880 (5) | 2.27 (3) | 3.120 (11) | 162 (9) |
C5G—H5G···Cl6Dii | 0.95 | 2.73 | 3.638 (10) | 160.9 |
N2H—H2H1···N1I | 0.881 (5) | 2.176 (15) | 3.045 (11) | 169 (3) |
N2H—H2H2···O4G | 0.880 (5) | 1.965 (15) | 2.842 (11) | 175 (9) |
N3H—H3H···N3G | 0.880 (5) | 2.00 (2) | 2.870 (11) | 169 (10) |
C5H—H5H···Cl6Ev | 0.95 | 2.93 | 3.837 (10) | 161.1 |
N2I—H2I1···N1H | 0.881 (5) | 2.04 (3) | 2.900 (12) | 165 (9) |
N3I—H3I···O4K | 0.880 (5) | 1.889 (17) | 2.764 (11) | 173 (10) |
N2K—H2K2···N2Svi | 0.880 (5) | 2.28 (4) | 3.13 (2) | 161 (8) |
N3K—H3K···O4I | 0.880 (5) | 1.882 (14) | 2.761 (11) | 176 (10) |
N2L—H2L1···N1K | 0.880 (5) | 2.14 (3) | 2.999 (11) | 164 (9) |
N2L—H2L2···N2O | 0.880 (5) | 2.59 (4) | 3.436 (14) | 162 (10) |
N3L—H3L···O4M | 0.77 (11) | 2.02 (12) | 2.782 (11) | 169 (12) |
N2M—H2M1···N1Gvii | 0.880 (5) | 2.050 (14) | 2.927 (11) | 175 (6) |
N3M—H3M···O4L | 0.96 (11) | 1.83 (11) | 2.794 (11) | 175 (10) |
N1O—H1O···O4Gviii | 0.97 (11) | 1.64 (12) | 2.598 (11) | 167 (10) |
N2O—H2O1···O4M | 0.881 (5) | 1.978 (12) | 2.810 (12) | 157 (3) |
N2O—H2O2···N1Rix | 0.881 (5) | 2.27 (8) | 2.971 (13) | 136 (10) |
N1P—H1P···O4Ax | 0.891 (5) | 2.007 (13) | 2.769 (10) | 142.8 (16) |
N2P—H2P1···O4B | 0.880 (5) | 1.89 (3) | 2.719 (11) | 157 (8) |
N2P—H2P2···O4H | 0.880 (5) | 2.11 (5) | 2.872 (11) | 144 (7) |
C3P—H3P···O4Lviii | 0.95 | 2.49 | 3.186 (11) | 130.3 |
N2R—H2R1···O4Fxi | 0.880 (5) | 2.36 (5) | 3.05 (2) | 136 (6) |
N2R—H2R2···O4E | 0.880 (5) | 2.12 (6) | 2.92 (2) | 152 (12) |
C3R—H3R···O4Dxii | 0.95 | 2.44 | 3.37 (4) | 166.8 |
C5R—H5R···O4Ixiii | 0.95 | 2.45 | 3.28 (2) | 144.7 |
C4O—H4O···O4Cxiv | 0.95 | 2.64 | 3.577 (12) | 170.5 |
Symmetry codes: (i) x−1, y+2, z; (ii) −x+2, −y−1, −z+1; (iii) x+1, y−2, z; (iv) x+2, y−1, z; (v) −x+2, −y−1, −z; (vi) x−2, y+2, z+1; (vii) x−2, y+1, z; (viii) −x, −y+1, −z+1; (ix) −x+1, −y−1, −z; (x) −x+2, −y, −z; (xi) −x+3, −y−3, −z; (xii) −x+3, −y−2, −z; (xiii) x+2, y−2, z−1; (xiv) −x+1, −y, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O4Bi | 0.88 (2) | 1.92 (4) | 2.765 (8) | 160 (9) |
N1A—H1A···Br5Bi | 0.88 (2) | 3.03 (9) | 3.525 (7) | 118 (7) |
N2A—H2A1···O4B | 0.87 (2) | 2.04 (4) | 2.871 (9) | 160 (10) |
N2A—H2A2···O4Aii | 0.88 (2) | 2.05 (6) | 2.807 (8) | 144 (9) |
N2B—H2B1···Br5Aiii | 0.891 (16) | 3.004 (13) | 3.852 (6) | 160 (2) |
N2B—H2B2···O4A | 0.894 (16) | 1.938 (19) | 2.831 (10) | 176 (9) |
N3B—H3B···N3A | 0.87 (2) | 2.03 (3) | 2.883 (10) | 164 (9) |
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. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O2X | 0.876 (10) | 1.90 (3) | 2.723 (6) | 155 (6) |
N2A—H21A···O2X | 0.876 (10) | 2.11 (3) | 2.919 (6) | 153 (6) |
N2A—H22A···O4B | 0.881 (10) | 1.968 (17) | 2.839 (6) | 170 (6) |
N2B—H21B···O4Ai | 0.875 (10) | 2.11 (4) | 2.887 (6) | 147 (6) |
N2B—H22B···O4A | 0.878 (10) | 1.983 (15) | 2.855 (6) | 172 (6) |
N3B—H3B···N3A | 0.876 (10) | 1.983 (16) | 2.850 (6) | 170 (6) |
Symmetry code: (i) −x+1, −y+1, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O4Bi | 0.879 (9) | 1.99 (3) | 2.810 (10) | 154 (7) |
N1A—H1A···Br5Bi | 0.879 (9) | 2.88 (9) | 3.429 (8) | 122 (8) |
N2A—H2A1···O4B | 0.878 (10) | 2.05 (3) | 2.901 (12) | 163 (10) |
N2A—H2A2···O4Aii | 0.879 (10) | 2.24 (8) | 2.872 (11) | 129 (9) |
N2A—H2A2···Br5Aii | 0.879 (10) | 2.97 (10) | 3.469 (8) | 118 (9) |
N2B—H2B1···N1Biii | 0.882 (11) | 2.244 (18) | 3.125 (13) | 178 (12) |
N2B—H2B2···O4A | 0.881 (10) | 2.03 (4) | 2.890 (11) | 164 (11) |
N3B—H3B···N3A | 0.880 (10) | 2.04 (3) | 2.903 (11) | 165 (10) |
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. |