research communications
Fifteen 4-(2-methoxyphenyl)piperazin-1-ium salts containing organic anions: supramolecular assembly in zero, one, two and three dimensions
aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru-570 006, India, bDepartment of Chemistry, Maharani's Science College for Women, Mysuru-570 001, India, cInstitute of Materials Science, Darmstadt University of Technology, Alarich-Weiss-Strasse 2, D-64287 Darmstadt, Germany, dDepartment of Bioinformatics, School of Earth, Biological and Environmental Sciences, Central University of South Bihar, Gaya 824236, India, and eSchool of Chemistry, University of St Andrews, St Andrews, Fife KY16 9ST, UK
*Correspondence e-mail: yathirajan@hotmail.com
Fifteen 4-(2-methoxyphenyl)piperazin-1-ium salts containing organic anions have been prepared and structurally characterized. In the isostructural 4-chlorobenzoate and 4-bromobenzoate salts, C11H17N2O+·C7H4ClO2− (I) and C11H17N2O+·C7H4BrO2− (II), and the 4-iodobenzoate salt C11H17N2O+·C7H4IO2− (III), the ions are linked by N—H⋯O hydrogen bonds, forming centrosymmetric R44(12) four-ion aggregates; a similar aggregate is formed in the 2-chlorobenzoate salt (V), isomeric with (I). In the 2-fluorobenzoate salt C11H17N2O+·C7H4FO2− (IV), and the isomorphous pair of salts, the 2-bromobenzoate (VI), isomeric with (II) and 2-iodobenzoate (VII), isomeric with (III), N—H⋯O and C—H⋯π(arene) interactions link the components into three-dimensional arrays. Four-ion R44(12) aggregates are also found in the 2-methylbenzoate, 4-aminobenzoate and 4-nitrobenzoate salts, C11H17N2O+·C8H7O2− (VIII), C11H17N2O+·C7H6NO2− (IX) and C11H17N2O+·C7H4NO4− (X), but those in (IX) are linked into complex sheets by an additional N—H⋯O hydrogen bond. In the 3,5-dinitrobenzoate salt, C11H17N2O+·C7H3N2O6−·2H2O (XI), N—H⋯O and O—H⋯O hydrogen bonds link the components into a complex ribbon structure. In the picrate salt, C11H17N2O+·C6H2N3O7− (XII), the four-ion aggregates are linked into chains of rings by C—H⋯O hydrogen bonds. In the hydrogen maleate salt, C11H17N2O+·C4H3O4− (XIII), two- and three-centre hydrogen bonds link the ions into a ribbon structure while both anions contain very short but asymmetric O—H⋯O hydrogen bonds, having O⋯O distances of 2.4447 (16) and 2.4707 (17) Å. O—H⋯O Hydrogen bonds link the anions in the hydrogen fumarate salt (XIV), isomeric with (XIII), into chains that are linked into sheets via N—H⋯O hydrogen bonds. In the hydrogen (2R,3R)-tartrate salt, C11H17N2O+·C4H5O6−·1.698H2O (XV), the anions are linked into sheets by O—H⋯O hydrogen bonds. Comparisons are made with the structures of some related compounds.
Keywords: synthesis; piperazines; crystal structure; molecular conformation; absolute configuration; disorder; hydrogen bonding; supramolecular assembly.
1. Chemical context
We have recently reported the molecular and supramolecular structures of the recreational drug N-(4-methoxyphenyl)piperazine (4-MeOPP) (Kiran Kumar et al., 2020) and those of a range of salts formed by 4-MeOPP with organic acids (Kiran Kumar, Yathirajan, Foro et al., 2019; Kiran Kumar et al. 2020), as well as those of a number of N-aroyl derivatives (Kiran Kumar, Yathirajan, Sagar et al., 2019). We have also reported the structures of some salts of N-(4-fluorophenyl)piperazine (4-FPP) (Harish Chinthal, Yathirajan, Archana et al., 2020; Harish Chinthal, Yathirajan, Kavitha et al., 2020). As a continuation of this study, we have now investigated a number of salts of the isomeric N-(2-methoxyphenyl)piperazine (2-MeOPP), which has been used as a building block in the synthesis of both 5-HT1A receptor ligands (Orjales et al., 1995) and dopamine D2 and D3 ligands (Hackling et al., 2003) and also as a building block for the synthesis of derivatives exhibiting antidepressant-like activity (Waszkielewicz et al., 2015). Here we report the syntheses and structures of the salts (I)–(XI) (Figs. 1–11) formed between 2-MeOPP and eleven aromatic carboxylic acids, along with a redetermination of the salt (XII) (Fig. 12) formed with 2,4,6-trinitrophenol (picric acid) where the reported structure (Verdonk et al., 1997; CSD refcode NEBGIK) shows signs of unmodelled disorder, and we report here also the structures of three acid salts (XIII)–(XV) (Figs. 13–15) formed with some aliphatic dicarboxylic acids. All of the salts (I)–(XV) were straightforwardly prepared by the acid–base reactions and subsequent crystallizations of equimolar mixtures of 2-MeOPP with the appropriate organic acid.
2. Structural commentary
Compounds (I) and (II) (Figs. 1 and 2) are isostructural in P. Although the 4-iodobenzoate analogue (III) (Fig. 3) also crystallizes in the same it is not isostructural with (I) and (II). Among the 2-halobenzoate salts, in the 2-fluorobenzoate (IV) the anion is disordered over two sets of atomic sites having occupancies 0.907 (8) and 0.093 (8) (Fig. 4). There is a significant peak, 1.15 e Å−3, in the final difference map for compound (V): it was originally thought that this might represent a partial-occupancy water molecule, although no associated H atoms could be located, but its distance from atom O32 is only 2.35 Å, which would require an unusually short O—H⋯O hydrogen bond for this assignment to be plausible. Consistent with this, examination of the refined, solvent-free structure of (V) using PLATON (Spek, 2020) showed that the structure contains no solvent-accessible void spaces. Compounds (VI) and (VII) are isomorphous, but whereas the components of (VI) are fully ordered (Fig. 6), in (VII) the carboxylate group in the anion is disordered over two sets of atomic sites having occupancies 0.54 (9) and 0.46 (9) (Fig. 7); hence, these isomorphous compounds cannot be regarded as strictly isostructural (cf. Acosta et al., 2009; Yépes et al., 2012; Shreekanth et al., 2020), because of the disorder in (VII). The structures of (VI) and (VII) are mutually inverse for the crystals selected for data collection, but this has no chemical significance. Compounds (VIII)–(X) (Figs. 8–10) all crystallize in solvent-free form, but the 3,5-dinitrobenzoate salt (XI) is a dihydrate (Fig. 11). The structure of the picrate salt (XII) was reported a number of years ago (Verdonk et al., 1997), but the deposited anisotropic displacement parameters suggest the presence of unmodelled disorder in one of the nitro groups. Accordingly, we have redetermined this structure and found, indeed, that one of the nitro groups is disordered over three sets of atomic sites having occupancies 0.850 (5), 0.080 (4) and 0.069 (4) (Fig. 12).
The solvent-free 1:1 acid salt (XIII) derived from maleic acid crystallizes with Z′ = 2 (Fig. 13). A search for possible additional revealed none, although the atomic coordinates of the two cations and the two anions are related by the approximate, but non-crystallographic translation (x, + y, z). In sharp contrast to compound (XIII), the 1:1 salt (XIV) derived from fumaric acid, which is isomeric with maleic acid, crystallizes with two independent hydrogen fumarate anions, each lying across a centre of inversion: one of the anions is fully ordered but the other is disordered over two sets of atomic sites having occupancies 0.572 (9) and 0.428 (9) (Fig. 14). The 1:1 acid salt (XV) derived from (2R,3R)-tartaric acid crystallizes as a dihydrate (Fig. 15).
In none of the salts reported does the cation exhibit any internal symmetry: hence all are conformationally chiral but, with the exception of compounds (VI) and (VII), the space groups indicate that equal numbers of both conformational enantiomers are present. For all compounds except (VII), the reference cation was selected to be one for which the ring-puckering angles θ (Cremer & Pople, 1975) is close to zero, as calculated for the atom sequence (N1,C2,C3,N4,C5,C6). For the crystal of (VII) chosen for data collection, the value of this angle is 177.2 (5)°, confirming that this salt and (VI) have opposite absolute structures. In all of the cations, the piperazine ring adopts a chair conformation with the N-aryl substituent in an equatorial site. In the 2-methoxyphenyl units, the methoxy C atom is always close to coplanar with the adjacent aryl ring: the displacement of this atom from the plane of the ring ranges from 0.038 (5) Å in compound (I) to 0.288 (5) Å in compound (VII). Associated with this near planarity, the two exocyclic C—C—O angles differ in each compound by ca 10°, as is usually observed in planar or near-planar alkoxyarenes (Seip & Seip, 1973; Ferguson et al., 1996).
The two independent ions in compound (XIII) both contain a very short O—H⋯O hydrogen bond (Table 1): while these are both nearly linear, the two O—H distances in each are significantly different, as established both by of the atomic coordinates for the H atom, and from the final difference maps.
3. Supramolecular features
The supramolecular assembly in the salts (I)–(XV) is based on N—H⋯O and O—H⋯O hydrogen bonds augmented in a number of cases by C—H⋯O and C—H⋯π(arene) hydrogen bonds. In general, we have discounted hydrogen bonds having D—H⋯A angles that are significantly less than 140°, as the interaction energies associated with such contacts are likely to be very low, so that these cannot be regarded as structurally significant (Wood et al., 2009). We have also discounted short contacts involving the H atoms of the methyl groups, as such groups are likely to be undergoing very rapid rotation about the adjacent C—O bonds (Riddell & Rogerson, 1996, 1997). Most of the C—H⋯π(arene) contacts have H⋯Cg distances in excess of 2.85 Å, and we have therefore only considered the effects of such contacts in the assembly of compounds (III) and (IV), where these distances are below 2.80 Å. It should perhaps be conceded here that these are somewhat arbitrary judgments, made with the primary aim of avoiding over-interpretation of the longer contacts and over-complication of the descriptions.
In each of the isostructural pair of compounds (I) and (II), two N—H⋯O hydrogen bonds (Table 1) link the ionic components into a centrosymmetric four-ion aggregate, characterized by an R44(12) (Etter, 1990; Etter et al., 1990; Bernstein et al., 1995) motif (Fig. 16). A similar motif occurs in the structure of compound (III) (Fig. 17), but the different orientations of the unit-cell outline in Figs. 16 and 17, illustrate the different arrangements of the components in compounds (I) and (II) on the one hand and compound (III) on the other. In (III), the four-ion aggregates are linked into chains by a C—H⋯π(arene) interaction, but the C—H⋯O contact in (III) has a very small D—H⋯A angle and is thus not structurally significant (Wood et al., 2009).
The hydrogen bonding involving the two disorder components in compound (IV) are very similar (Table 1) and thus only the major component needs to be considered here. The combination of two N—H⋯O hydrogen bonds and one C—H⋯π(arene) hydrogen bond, involving atom C34 as the donor, links the ions into a three-dimensional network, whose formation is readily analysed in terms of three one-dimensional sub-structures (Ferguson et al., 1998a,b; Gregson et al., 2000). In addition to the N—H⋯O hydrogen bond forming the which defines the selected we consider in turn the linking of these ion pairs by the action of the N—H⋯O hydrogen bond involving atom H12, acting alone; by that of the C—H⋯π(arene) hydrogen bond acting alone; and finally by that of the two hydrogen bonds in combination. The ion pairs are linked by a second N—H⋯O hydrogen bond to form a C22(6) chain running parallel to the [001] direction (Fig. 18), and they are linked by the C—H⋯π(arene) hydrogen bond to form a chain running parallel to [101] (Fig. 19). The N—H⋯O and C—H⋯π hydrogen bonds, acting alternately, generate a chain running parallel to the [112] direction (Fig. 20), and the combination of chains running parallel to [001], [101] and [112] suffices to generate a three-dimensional structure. In the 2-chlorobenzoate analogue, compound (V), two independent N-H⋯O hydrogen bonds again link the ions into a centrosymmetric R44(12) motif, of the type observed in compounds (I)–(III). There are two C—H⋯π(arene) contacts in (V), but these are both long, and probably not structurally significant.
The ion pairs in compounds (VI) and (VII) are again linked into three-dimensional arrays, by a combination of N—H⋯O and C—H⋯O hydrogen bonds, as opposed to the N—H⋯O and C—H⋯π(arene) interactions in the structure of (IV). An N—H⋯O hydrogen bond links ion pairs which are related by the 21 screw axis along (x, 1/4, 1/2) to form a C21(4) chain along [100] (Fig. 21). In addition, the ion pairs which are related by the 21 screw axis along (1/4, 1/2, z) are linked by a C—H⋯O hydrogen bond to form a C22(12) chain along [001] (Fig. 22), while the alternating action of the N—H⋯O and C—H⋯O hydrogen bonds generates a chain running parallel to the [010] direction (Fig. 23). The combination of chains along [100], [010] and [001] thus generates a three-dimensional array.
The ions in compound (VIII) are linked by two N—H⋯O hydrogen bonds to form an R44(12) four-ion aggregate analogous to those observed in compounds (I)–(III) and (V). Similar four-ion aggregates are also found in compounds (IX) and (X), but in (IX) they are linked by a further N—H⋯O hydrogen bond, involving the amino group, to form a complex sheet lying parallel to (100) (Fig. 24). In the dihydrate (XI), each water molecule acts as a single acceptor and a double donor of hydrogen bonds (Table 1), and supramolecular aggregation takes the form of a complex ribbon running parallel to the [100] direction (Fig. 25). In the picrate salt (XII), a combination of two independent N—H⋯O hydrogen bonds links the components into a centrosymmetric four-ion aggregate of R44(16) type, where the two acceptor are the phenolic atom O31 and one of the nitro O atoms (Fig. 26). Aggregates of this type are weakly linked into a chain of rings by a C—H⋯O hydrogen bond.
In compound (XIII), where Z′ = 2, each of the anions contains a very short O—H⋯O hydrogen bond, although in each of these interactions the two O—H distances are significantly different (Table 1). The supramolecular assembly depends upon three independent two-centre N—H⋯O hydrogen bonds and one three-centre N—H⋯(O)2 hydrogen bond. These link the ions into a ribbon, or molecular ladder, running parallel to the [010] direction and in which R24(14) rings centred at (0, n + 1/2, 1/2) alternate with R88(30) rings centred at (0, n, 1/2), where n represents an integer in each case (Fig. 27). Analysis of the supramolecular assembly in compound (XIV) is complicated by the combination of centrosymmetric anions and the disorder exhibited by one of them. However, since the hydrogen bonds involving the two disorder components are very similar, only the major disorder components need to be considered here. The ordered anions are linked by O—H⋯O hydrogen bonds into a chain along (x, 0, 1) and the disordered anions are similarly linked into a chain along (x, 1/2, 1). The two types of chain, which alternate along the [010] direction, are linked by the cations to form a sheet of R66(26) rings lying parallel to (001) (Fig. 28). In the structure of compound (XV), the anions are linked by three independent O—H⋯O hydrogen bonds, in which both of the hydroxyl groups as well as the carboxyl group act as donors, to form a sheet lying parallel to (001), in which both R44(18) and R44(20) rings can be identified (Fig. 29). The cations and the water molecules are tethered to this sheet, markedly increasing its complexity but without changing the dimensionality of the overall assembly. The result is a thick tripartite sheet, occupying the whole domain 0 < z < 1.0 and having a hydrogen-bonded layer in the centre with the on the outside surfaces: there are no direction-specific interactions between adjacent sheets.
In summary, therefore, the hydrogen-bonded assembly is finite, or zero-dimensional in compounds (I)–(III), (V), (VIII) and (X); one-dimensional in (XI), (XII) and (XIII); two-dimensional in (IX), (XIV) and (XV); and three–dimensional in (IV), (VI) and (VII).
4. Database survey
It is of interest briefly to compare the structures of the compounds reported here with those of some closely related examples, in particular the salts formed by the isomeric N-(4-methoxyphenyl)piperazine (4-MeOPP) and the analogous N-(4-fluorophenyl)piperazine (4-FPP). The salts formed between 4-MeOPP and the benzoic acids 4-XC6H4COOH, where X = H, F, Cl, and Br, all crystallize as stoichiometric monohydrates and they are all isomorphous in P (Kiran Kumar, Yathirajan, Foro et al., 2019), a combination of N—H⋯O, O—H⋯O, C—H⋯O and C—H⋯π(arene) hydrogen bonds links the components into complex sheets. By contrast, compounds (I)–(III) reported here all crystallize in solvent-free form and all form finite centrosymmetric four-ion aggregates (Figs. 16 and 17). The salt formed between 4-MeOPP and 4-aminobenzoate crystallizes as a monohydrate (Kiran Kumar et al., 2020), as compared with the solvent free analogues (IX) reported here, and the components are linked by a combination of N—H⋯O, O—H⋯O and C—H⋯π(arene) hydrogen bonds to form a three-dimensional assembly, as compared with the two-dimensional assembly in (IX). The 3,5-dinitrobenzoate salt with 4-MeOPP crystallizes in solvent-free form (Kiran Kumar et al., 2020), as opposed to the dihydrate (XI) reported here, and the component ions are linked into the simple R44(12) motif found here for compounds (I)–(III), (VIII) and (X). The picrate salt of 4-MeOPP exhibits orientational disorder in one of the nitro groups (Kiran Kumar et al., 2020), as observed in compound (XII) here, but the supramolecular aggregation is more complex than the simple aggregate found for (XII), in that a combination of N—H⋯O and C—H⋯π(arene) hydrogen bonds generates a sheet structure. The anion in the hydrogen maleate salt of 4-MeOPP, which crystallizes with Z′ = 1 (Kiran Kumar, Yathirajan, Foro et al., 2019) unlike the Z′ = 2 for compound (XIII), contains a very short, but unsymmetrical O—H⋯O hydrogen bond, and the ions are linked into a chain of rings by a combination of two-centre N—H⋯O and three-centre N—H⋯(O,O) hydrogen bonds. By contrast with compound (XIV) reported here where there are two independent hydrogen fumarate anions each lying across a centre of inversion, in the hydrogen fumarate salt of 4-MeOPP, there is only one type of anion, although this exhibits some orientational disorder and Z′ = 1: a combination of N—H⋯O and O—H⋯O and C—H⋯π(arene) hydrogen bonds links the ions into a three-dimensional structure, as opposed to the two-dimensional structure of (XIV). Finally, we note some salts formed by 4-FPP with organic acids (Harish Chinthal, Yathirajan, Archana et al., 2020; Harish Chinthal, Yathirajan, Kavitha et al., 2020). The 2-fluorobenzoate crystallizes as a stoichiometric monohydrate, and the 2-bromobenzoate as a partial hydrate, while the 2-iodobenzoate crystallizes in solvent-free form (Harish Chinthal, Yathirajan, Kavitha et al., 2020), in contrast to compounds (IV)–(VII), which are all solvent-free, and the 3,5-dinitrobenzoate salt of 4-FPP is also solvent-free, as opposed to the dihydrate (XI). The 1:1 acid salt formed between (2R,3R)-tartaric acid and 4-FPP crystallizes as a monohydrate (Harish Chinthal, Yathirajan, Archana et al., 2020), whereas the analogous compound (XV) crystallizes as a 1.70 (hydrate).
5. Synthesis and crystallization
All reagents were obtained commercially, and all were used as received. For the synthesis of compounds (I)–(XV), solutions of N-(2-methoxyphenyl)piperazine (100 mg, 0.52 mmol) in methanol (10 ml) were mixed with an equimolar quantity of the appropriate acid [4-chlorobenzoic acid (82 mg) for (I), 4-bromobenzoic acid (103 mg) for (II), 4-iodobenzoic acid (129 mg) for (III), 2-fluorobenzoic acid (73 mg) for (IV), 2-chlorobenzoic acid (82 mg) for (V), 2-bromobenzoic acid (103 mg) for (VI), 2-iodobenzoic acid (129 mg) for (VII), 2-methylbenzoic acid (71 mg) for (VIII), 4-aminobenzoic acid (72 mg) for (IX), 4-nitrobenzoic acid (97 mg) for (X), 3,5-dinitrobenzoic acid (110 mg) for (XI), picric acid (120 mg) for (XII), maleic acid (61 mg) for (XIII), fumaric acid (61 mg) for (XIV) and (2R,3R)-tartaric acid (78 mg) for (XV)] also dissolved in methanol (10 ml). These mixtures were then heated briefly at 323 K with magnetic stirring and then set aside to crystallize at room temperature. The resulting products were then collected by filtration and dried in air. Crystals suitable for single-crystal X-ray diffraction were grown by slow evaporation, at ambient temperature and in the presence of air, of solutions in acetone/acetonitrile (initial composition 1:1, v/v) for (I), methanol/acetonitrile (1:6, v/v) for (II), methanol/acetonitrile (1:1, v/v) for (III), ethyl acetate/acetone (2:1, v/v) for (IV) and (V), methanol/ethyl acetate (1:7, v/v) for (VI) and (VII), methanol for (VIII), (X), and (XIII)–(XV), methanol/ethyl acetate (3:2, v/v) for (IX), and methanol/ethyl acetate (1:1, v/v) for (XI) and (XII). M.p. (I) 374–378 K, (II) 390–394 K, (III) 422–428 K, (IV) 384–387 K, (V) 396–389 K, (VI) 396–399 K, (VII) 402–408 K, (VIII) 389–393 K, (IX) 441–445 K, (X) 408–412 K, (XI) 437–442 K, (XII) 430–435 K, (XIII) 390–396 K, (XIV) 435–437 K, (XV) 407–411 K.
6. Refinement
Crystal data, data collection and . Two bad outlier reflections [(1,4,0) and (1,2,2)] were removed from the dataset for compound (V), and one bad outlier reflection (0,,13) was removed from the dataset for compound (XV) before the final refinements. For compound (IV), calculation of the Flack x parameter (Flack, 1983) using 1089 quotients of the type [(I+) − (I−)]/[(I+) + (I−)] (Parsons et al., 2013) gave a value 0.2 (3) in the absence of significant the correct orientation of the structure of (IV) with respect to the polar axis directions remains uncertain. The correct absolute configurations for compounds (VI) and (VII) were established from the Flack x parameters: for (VI) x = 0.004 (5) calculated using 919 coefficients, and for (VII) x = 0.004 (10) calculated using 1045 coefficients. For the minor disorder component in compound (IV), the bonded distances and the 1,3-non-bonded distances were restrained to be the same as the corresponding distances in the major disorder components, subject to s.u. values of 0.01 and 0.02 Å, respectively, and the anisotropic displacement parameters for corresponding pairs of atoms in the two disorder components were constrained to be the same, giving occupancies of 0.907 (8) and 0.093 (8). Similar distance restraints were applied to the disordered carboxylate group in compound (VII), where the displacement parameters for the disordered O atoms were subjected to similarity restraints, giving occupancies of 0.53 (9) and 0.47 (9). The disordered nitro group in compound (XII) was modelled over three sets of atomic sites, with similar restraints to those imposed in (VII) giving occupancies of 0.860 (5), 0.080 (4) and 0.069 (4). All H atoms, apart from those in the minor disorder component of compound (IV) and in the partial-occupancy water molecule in compound (V), were located in difference maps. The H atoms bonded to C atoms, apart from those in the disordered anion of compound (XIV) which were permitted to ride at the locations found in difference maps, were then treated as riding atoms in geometrically idealized positions with C—H distances of 0.93 Å (alkenyl and aromatic), 0.96 Å (CH3), 0.97 Å (CH2) or 0.98 Å (aliphatic C—H), and with Uiso(H) = kUeq(C), where k = 1.5 for the methyl groups, which were permitted to rotate but not to tilt, and 1.2 for all other H atoms bonded to C atoms: the H atoms in the minor disorder component of compound (IV) were included on exactly the same basis. For the H atoms bonded to N atoms, these were treated as riding atoms in the disordered structures (VII) and (XIV) with N—H distances of 0.89 Å and UisoH = 1.2Ueq(N), but in all other compounds, the atomic coordinates of the H atoms bonded to N atoms were refined with UisoH = 1.2Ueq(N), giving the N—H distances shown in Table 1. For the H atoms bonded to O atoms in compounds (XI), (XIII) and (XV), the atomic coordinates were refined with Uiso(H) = 1.5Ueq(O), giving the O—H distances shown in Table 1, but the partial occupancy H atoms bonded to O atoms in compound (XIV) were treated as riding atoms with O—H = 0.82 Å and Uiso(H) = 1.5Ueq(O).
details are summarized in Table 2
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Supporting information
https://doi.org/10.1107/S2056989020014097/hb7950sup1.cif
contains datablocks global, I, II, III, IV, V, VI, VII, VIII, IX, X, XI, XII, XIII, XIV, XV. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989020014097/hb7950Isup2.hkl
Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S2056989020014097/hb7950IIsup3.hkl
Structure factors: contains datablock III. DOI: https://doi.org/10.1107/S2056989020014097/hb7950IIIsup4.hkl
Structure factors: contains datablock IV. DOI: https://doi.org/10.1107/S2056989020014097/hb7950IVsup5.hkl
Structure factors: contains datablock V. DOI: https://doi.org/10.1107/S2056989020014097/hb7950Vsup6.hkl
Structure factors: contains datablock VI. DOI: https://doi.org/10.1107/S2056989020014097/hb7950VIsup7.hkl
Structure factors: contains datablock VII. DOI: https://doi.org/10.1107/S2056989020014097/hb7950VIIsup8.hkl
Structure factors: contains datablock VIII. DOI: https://doi.org/10.1107/S2056989020014097/hb7950VIIIsup9.hkl
Structure factors: contains datablock IX. DOI: https://doi.org/10.1107/S2056989020014097/hb7950IXsup10.hkl
Structure factors: contains datablock X. DOI: https://doi.org/10.1107/S2056989020014097/hb7950Xsup11.hkl
Structure factors: contains datablock XI. DOI: https://doi.org/10.1107/S2056989020014097/hb7950XIsup12.hkl
Structure factors: contains datablock XII. DOI: https://doi.org/10.1107/S2056989020014097/hb7950XIIsup13.hkl
Structure factors: contains datablock XIII. DOI: https://doi.org/10.1107/S2056989020014097/hb7950XIIIsup14.hkl
Structure factors: contains datablock XIV. DOI: https://doi.org/10.1107/S2056989020014097/hb7950XIVsup15.hkl
Structure factors: contains datablock XV. DOI: https://doi.org/10.1107/S2056989020014097/hb7950XVsup16.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989020014097/hb7950Isup17.cml
Supporting information file. DOI: https://doi.org/10.1107/S2056989020014097/hb7950IIsup18.cml
Supporting information file. DOI: https://doi.org/10.1107/S2056989020014097/hb7950IIIsup19.cml
Supporting information file. DOI: https://doi.org/10.1107/S2056989020014097/hb7950IVsup20.cml
Supporting information file. DOI: https://doi.org/10.1107/S2056989020014097/hb7950Vsup21.cml
Supporting information file. DOI: https://doi.org/10.1107/S2056989020014097/hb7950VIsup22.cml
Supporting information file. DOI: https://doi.org/10.1107/S2056989020014097/hb7950VIIsup23.cml
Supporting information file. DOI: https://doi.org/10.1107/S2056989020014097/hb7950VIIIsup24.cml
Supporting information file. DOI: https://doi.org/10.1107/S2056989020014097/hb7950IXsup25.cml
Supporting information file. DOI: https://doi.org/10.1107/S2056989020014097/hb7950Xsup26.cml
Supporting information file. DOI: https://doi.org/10.1107/S2056989020014097/hb7950XIsup27.cml
Supporting information file. DOI: https://doi.org/10.1107/S2056989020014097/hb7950XIIsup28.cml
Supporting information file. DOI: https://doi.org/10.1107/S2056989020014097/hb7950XIIIsup29.cml
Supporting information file. DOI: https://doi.org/10.1107/S2056989020014097/hb7950XIVsup30.cml
For all structures, data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell
CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2020); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b) and PLATON (Spek, 2020).C11H17N2O+·C7H4ClO2− | Z = 2 |
Mr = 348.82 | F(000) = 368 |
Triclinic, P1 | Dx = 1.318 Mg m−3 |
a = 7.401 (1) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 7.888 (1) Å | Cell parameters from 3770 reflections |
c = 15.410 (3) Å | θ = 2.6–27.8° |
α = 100.28 (2)° | µ = 0.24 mm−1 |
β = 94.40 (1)° | T = 296 K |
γ = 94.14 (1)° | Plate, orange |
V = 879.2 (2) Å3 | 0.44 × 0.28 × 0.16 mm |
Oxford Diffraction Xcalibur with Sapphire CCD diffractometer | 3763 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 2318 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.019 |
ω scans | θmax = 27.5°, θmin = 2.6° |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | h = −9→8 |
Tmin = 0.884, Tmax = 0.963 | k = −10→6 |
6241 measured reflections | l = −19→19 |
Refinement on F2 | Primary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.053 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.131 | w = 1/[σ2(Fo2) + (0.0498P)2 + 0.3034P] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max < 0.001 |
3763 reflections | Δρmax = 0.19 e Å−3 |
224 parameters | Δρmin = −0.27 e Å−3 |
0 restraints |
Experimental. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. |
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 | ||
N1 | 0.3863 (3) | 0.5719 (3) | 0.61980 (13) | 0.0537 (6) | |
H11 | 0.349 (3) | 0.654 (3) | 0.5787 (16) | 0.064* | |
H12 | 0.494 (4) | 0.526 (3) | 0.6072 (17) | 0.064* | |
C2 | 0.2453 (4) | 0.4243 (3) | 0.61032 (16) | 0.0595 (7) | |
H2A | 0.2389 | 0.3567 | 0.5509 | 0.071* | |
H2B | 0.1276 | 0.4677 | 0.6194 | 0.071* | |
C3 | 0.2901 (4) | 0.3104 (3) | 0.67711 (14) | 0.0492 (6) | |
H3A | 0.1964 | 0.2154 | 0.6709 | 0.059* | |
H3B | 0.4051 | 0.2623 | 0.6665 | 0.059* | |
N4 | 0.3016 (3) | 0.4131 (2) | 0.76645 (11) | 0.0417 (5) | |
C5 | 0.4446 (3) | 0.5568 (3) | 0.77727 (15) | 0.0456 (6) | |
H5A | 0.5614 | 0.5111 | 0.7685 | 0.055* | |
H5B | 0.4511 | 0.6234 | 0.8369 | 0.055* | |
C6 | 0.4046 (4) | 0.6728 (3) | 0.71121 (15) | 0.0489 (6) | |
H6A | 0.2928 | 0.7261 | 0.7232 | 0.059* | |
H6B | 0.5023 | 0.7641 | 0.7173 | 0.059* | |
C21 | 0.3080 (3) | 0.3202 (3) | 0.83759 (14) | 0.0402 (5) | |
C22 | 0.2709 (3) | 0.4034 (3) | 0.92205 (14) | 0.0401 (5) | |
C23 | 0.2740 (3) | 0.3164 (3) | 0.99224 (16) | 0.0500 (6) | |
H23 | 0.2531 | 0.3740 | 1.0482 | 0.060* | |
C24 | 0.3080 (4) | 0.1439 (3) | 0.97981 (17) | 0.0565 (7) | |
H24 | 0.3088 | 0.0854 | 1.0272 | 0.068* | |
C25 | 0.3405 (4) | 0.0595 (3) | 0.89756 (18) | 0.0588 (7) | |
H25 | 0.3615 | −0.0569 | 0.8889 | 0.071* | |
C26 | 0.3420 (3) | 0.1471 (3) | 0.82735 (16) | 0.0498 (6) | |
H26 | 0.3663 | 0.0889 | 0.7721 | 0.060* | |
O22 | 0.2258 (2) | 0.5712 (2) | 0.92836 (10) | 0.0522 (4) | |
C27 | 0.2117 (4) | 0.6682 (3) | 1.01422 (15) | 0.0539 (6) | |
H27A | 0.1780 | 0.7816 | 1.0093 | 0.081* | |
H27B | 0.3267 | 0.6779 | 1.0488 | 0.081* | |
H27C | 0.1207 | 0.6107 | 1.0426 | 0.081* | |
C31 | 0.2111 (3) | 0.8543 (3) | 0.37936 (15) | 0.0450 (6) | |
C32 | 0.1780 (4) | 0.8004 (3) | 0.28892 (17) | 0.0597 (7) | |
H32 | 0.1867 | 0.6850 | 0.2643 | 0.072* | |
C33 | 0.1321 (4) | 0.9151 (4) | 0.23404 (17) | 0.0622 (7) | |
H33 | 0.1104 | 0.8772 | 0.1732 | 0.075* | |
C34 | 0.1190 (3) | 1.0848 (3) | 0.27049 (16) | 0.0498 (6) | |
Cl34 | 0.06196 (11) | 1.23102 (10) | 0.20197 (5) | 0.0724 (3) | |
C35 | 0.1471 (5) | 1.1410 (3) | 0.35980 (18) | 0.0712 (9) | |
H35 | 0.1353 | 1.2559 | 0.3843 | 0.085* | |
C36 | 0.1932 (5) | 1.0247 (3) | 0.41347 (17) | 0.0697 (9) | |
H36 | 0.2127 | 1.0631 | 0.4744 | 0.084* | |
C37 | 0.2650 (4) | 0.7306 (3) | 0.43954 (18) | 0.0529 (6) | |
O31 | 0.2833 (4) | 0.7908 (3) | 0.52081 (13) | 0.0955 (8) | |
O32 | 0.2879 (3) | 0.5797 (2) | 0.40612 (13) | 0.0704 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0757 (16) | 0.0508 (13) | 0.0397 (12) | 0.0186 (11) | 0.0112 (11) | 0.0142 (10) |
C2 | 0.079 (2) | 0.0591 (16) | 0.0380 (14) | 0.0075 (14) | −0.0055 (13) | 0.0050 (12) |
C3 | 0.0626 (16) | 0.0437 (13) | 0.0383 (13) | 0.0038 (12) | −0.0001 (11) | 0.0014 (10) |
N4 | 0.0525 (12) | 0.0389 (10) | 0.0326 (10) | 0.0038 (9) | 0.0011 (9) | 0.0048 (8) |
C5 | 0.0538 (15) | 0.0426 (13) | 0.0393 (13) | 0.0030 (11) | 0.0035 (11) | 0.0057 (10) |
C6 | 0.0641 (17) | 0.0412 (13) | 0.0419 (13) | 0.0079 (12) | 0.0088 (12) | 0.0063 (10) |
C21 | 0.0399 (13) | 0.0386 (12) | 0.0416 (13) | 0.0046 (10) | 0.0003 (10) | 0.0072 (10) |
C22 | 0.0420 (13) | 0.0385 (12) | 0.0402 (13) | 0.0065 (10) | 0.0027 (10) | 0.0075 (10) |
C23 | 0.0566 (16) | 0.0540 (15) | 0.0411 (14) | 0.0043 (12) | 0.0040 (11) | 0.0131 (11) |
C24 | 0.0690 (18) | 0.0498 (15) | 0.0544 (16) | 0.0031 (13) | −0.0027 (13) | 0.0240 (13) |
C25 | 0.0725 (19) | 0.0388 (13) | 0.0652 (18) | 0.0073 (12) | −0.0056 (14) | 0.0143 (13) |
C26 | 0.0602 (16) | 0.0420 (13) | 0.0458 (14) | 0.0077 (11) | 0.0015 (12) | 0.0046 (11) |
O22 | 0.0747 (12) | 0.0445 (9) | 0.0404 (9) | 0.0210 (8) | 0.0131 (8) | 0.0070 (7) |
C27 | 0.0599 (17) | 0.0488 (14) | 0.0502 (15) | 0.0053 (12) | 0.0115 (13) | −0.0012 (12) |
C31 | 0.0465 (14) | 0.0442 (13) | 0.0452 (14) | 0.0083 (11) | 0.0072 (11) | 0.0075 (11) |
C32 | 0.0740 (19) | 0.0551 (16) | 0.0502 (16) | 0.0264 (14) | 0.0077 (14) | 0.0010 (12) |
C33 | 0.0737 (19) | 0.0767 (19) | 0.0376 (14) | 0.0250 (15) | 0.0068 (13) | 0.0065 (13) |
C34 | 0.0507 (15) | 0.0572 (15) | 0.0455 (14) | 0.0055 (12) | 0.0047 (12) | 0.0197 (12) |
Cl34 | 0.0783 (5) | 0.0800 (5) | 0.0671 (5) | 0.0054 (4) | −0.0011 (4) | 0.0394 (4) |
C35 | 0.119 (3) | 0.0433 (15) | 0.0511 (17) | 0.0156 (16) | −0.0029 (16) | 0.0085 (12) |
C36 | 0.120 (3) | 0.0498 (15) | 0.0375 (14) | 0.0171 (16) | −0.0043 (15) | 0.0048 (12) |
C37 | 0.0586 (16) | 0.0494 (15) | 0.0546 (16) | 0.0122 (12) | 0.0095 (13) | 0.0153 (12) |
O31 | 0.175 (2) | 0.0646 (13) | 0.0529 (13) | 0.0405 (14) | −0.0007 (14) | 0.0189 (10) |
O32 | 0.0899 (15) | 0.0484 (11) | 0.0781 (13) | 0.0266 (10) | 0.0171 (11) | 0.0138 (10) |
N1—C6 | 1.481 (3) | C24—C25 | 1.370 (4) |
N1—C2 | 1.485 (3) | C24—H24 | 0.9300 |
N1—H11 | 1.02 (3) | C25—C26 | 1.385 (3) |
N1—H12 | 0.92 (3) | C25—H25 | 0.9300 |
C2—C3 | 1.516 (3) | C26—H26 | 0.9300 |
C2—H2A | 0.9700 | O22—C27 | 1.421 (3) |
C2—H2B | 0.9700 | C27—H27A | 0.9600 |
C3—N4 | 1.461 (3) | C27—H27B | 0.9600 |
C3—H3A | 0.9700 | C27—H27C | 0.9600 |
C3—H3B | 0.9700 | C31—C36 | 1.373 (3) |
N4—C21 | 1.423 (3) | C31—C32 | 1.380 (3) |
N4—C5 | 1.471 (3) | C31—C37 | 1.515 (3) |
C5—C6 | 1.512 (3) | C32—C33 | 1.386 (3) |
C5—H5A | 0.9700 | C32—H32 | 0.9300 |
C5—H5B | 0.9700 | C33—C34 | 1.369 (4) |
C6—H6A | 0.9700 | C33—H33 | 0.9300 |
C6—H6B | 0.9700 | C34—C35 | 1.364 (3) |
C21—C26 | 1.389 (3) | C34—Cl34 | 1.750 (2) |
C21—C22 | 1.406 (3) | C35—C36 | 1.384 (3) |
C22—O22 | 1.377 (2) | C35—H35 | 0.9300 |
C22—C23 | 1.380 (3) | C36—H36 | 0.9300 |
C23—C24 | 1.384 (3) | C37—O32 | 1.239 (3) |
C23—H23 | 0.9300 | C37—O31 | 1.251 (3) |
C6—N1—C2 | 110.65 (19) | C22—C23—H23 | 119.8 |
C6—N1—H11 | 107.0 (14) | C24—C23—H23 | 119.8 |
C2—N1—H11 | 109.8 (15) | C25—C24—C23 | 119.8 (2) |
C6—N1—H12 | 109.8 (17) | C25—C24—H24 | 120.1 |
C2—N1—H12 | 106.9 (16) | C23—C24—H24 | 120.1 |
H11—N1—H12 | 113 (2) | C24—C25—C26 | 120.1 (2) |
N1—C2—C3 | 110.5 (2) | C24—C25—H25 | 120.0 |
N1—C2—H2A | 109.6 | C26—C25—H25 | 120.0 |
C3—C2—H2A | 109.6 | C25—C26—C21 | 121.5 (2) |
N1—C2—H2B | 109.6 | C25—C26—H26 | 119.3 |
C3—C2—H2B | 109.6 | C21—C26—H26 | 119.3 |
H2A—C2—H2B | 108.1 | C22—O22—C27 | 117.86 (17) |
N4—C3—C2 | 109.35 (19) | O22—C27—H27A | 109.5 |
N4—C3—H3A | 109.8 | O22—C27—H27B | 109.5 |
C2—C3—H3A | 109.8 | H27A—C27—H27B | 109.5 |
N4—C3—H3B | 109.8 | O22—C27—H27C | 109.5 |
C2—C3—H3B | 109.8 | H27A—C27—H27C | 109.5 |
H3A—C3—H3B | 108.3 | H27B—C27—H27C | 109.5 |
C21—N4—C3 | 116.59 (17) | C36—C31—C32 | 117.8 (2) |
C21—N4—C5 | 113.53 (18) | C36—C31—C37 | 120.7 (2) |
C3—N4—C5 | 110.53 (18) | C32—C31—C37 | 121.5 (2) |
N4—C5—C6 | 110.35 (19) | C31—C32—C33 | 121.2 (2) |
N4—C5—H5A | 109.6 | C31—C32—H32 | 119.4 |
C6—C5—H5A | 109.6 | C33—C32—H32 | 119.4 |
N4—C5—H5B | 109.6 | C34—C33—C32 | 119.2 (2) |
C6—C5—H5B | 109.6 | C34—C33—H33 | 120.4 |
H5A—C5—H5B | 108.1 | C32—C33—H33 | 120.4 |
N1—C6—C5 | 110.38 (19) | C35—C34—C33 | 120.9 (2) |
N1—C6—H6A | 109.6 | C35—C34—Cl34 | 119.4 (2) |
C5—C6—H6A | 109.6 | C33—C34—Cl34 | 119.7 (2) |
N1—C6—H6B | 109.6 | C34—C35—C36 | 119.0 (2) |
C5—C6—H6B | 109.6 | C34—C35—H35 | 120.5 |
H6A—C6—H6B | 108.1 | C36—C35—H35 | 120.5 |
C26—C21—C22 | 117.5 (2) | C31—C36—C35 | 121.9 (2) |
C26—C21—N4 | 123.2 (2) | C31—C36—H36 | 119.1 |
C22—C21—N4 | 119.20 (19) | C35—C36—H36 | 119.1 |
O22—C22—C23 | 123.4 (2) | O32—C37—O31 | 124.7 (2) |
O22—C22—C21 | 115.91 (18) | O32—C37—C31 | 119.0 (2) |
C23—C22—C21 | 120.7 (2) | O31—C37—C31 | 116.3 (2) |
C22—C23—C24 | 120.4 (2) | ||
C6—N1—C2—C3 | −56.8 (3) | C24—C25—C26—C21 | −1.1 (4) |
N1—C2—C3—N4 | 58.6 (3) | C22—C21—C26—C25 | −0.3 (4) |
C2—C3—N4—C21 | 168.3 (2) | N4—C21—C26—C25 | −177.6 (2) |
C2—C3—N4—C5 | −60.1 (3) | C23—C22—O22—C27 | 10.9 (3) |
C21—N4—C5—C6 | −167.25 (18) | C21—C22—O22—C27 | −171.5 (2) |
C3—N4—C5—C6 | 59.6 (2) | C36—C31—C32—C33 | 1.3 (4) |
C2—N1—C6—C5 | 55.6 (3) | C37—C31—C32—C33 | −178.7 (2) |
N4—C5—C6—N1 | −56.8 (3) | C31—C32—C33—C34 | −0.2 (4) |
C3—N4—C21—C26 | 13.9 (3) | C32—C33—C34—C35 | −1.3 (4) |
C5—N4—C21—C26 | −116.3 (2) | C32—C33—C34—Cl34 | 179.8 (2) |
C3—N4—C21—C22 | −163.3 (2) | C33—C34—C35—C36 | 1.4 (5) |
C5—N4—C21—C22 | 66.5 (3) | Cl34—C34—C35—C36 | −179.6 (2) |
C26—C21—C22—O22 | −175.8 (2) | C32—C31—C36—C35 | −1.2 (5) |
N4—C21—C22—O22 | 1.6 (3) | C37—C31—C36—C35 | 178.9 (3) |
C26—C21—C22—C23 | 1.9 (3) | C34—C35—C36—C31 | −0.2 (5) |
N4—C21—C22—C23 | 179.3 (2) | C36—C31—C37—O32 | −176.7 (3) |
O22—C22—C23—C24 | 175.4 (2) | C32—C31—C37—O32 | 3.3 (4) |
C21—C22—C23—C24 | −2.1 (4) | C36—C31—C37—O31 | 3.2 (4) |
C22—C23—C24—C25 | 0.6 (4) | C32—C31—C37—O31 | −176.7 (3) |
C23—C24—C25—C26 | 1.0 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H11···O31 | 1.02 (2) | 1.60 (2) | 2.616 (3) | 176 (2) |
N1—H12···O32i | 0.92 (3) | 1.88 (3) | 2.792 (3) | 173 (2) |
C3—H3A···Cg1i | 0.97 | 2.96 | 3.881 (3) | 160 |
Symmetry code: (i) −x+1, −y+1, −z+1. |
C11H17N2O+·C7H4BrO2− | Z = 2 |
Mr = 393.27 | F(000) = 404 |
Triclinic, P1 | Dx = 1.468 Mg m−3 |
a = 7.4313 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 7.9163 (5) Å | Cell parameters from 3779 reflections |
c = 15.5212 (9) Å | θ = 2.6–27.6° |
α = 101.565 (5)° | µ = 2.33 mm−1 |
β = 94.780 (5)° | T = 296 K |
γ = 92.691 (5)° | Plate, yellow |
V = 889.54 (10) Å3 | 0.42 × 0.42 × 0.12 mm |
Oxford Diffraction Xcalibur with Sapphire CCD diffractometer | 3739 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 2989 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.018 |
ω scans | θmax = 27.6°, θmin = 2.6° |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | h = −9→8 |
Tmin = 0.258, Tmax = 0.756 | k = −10→10 |
5996 measured reflections | l = −19→16 |
Refinement on F2 | Primary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.043 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.115 | w = 1/[σ2(Fo2) + (0.0576P)2 + 0.570P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
3739 reflections | Δρmax = 0.84 e Å−3 |
224 parameters | Δρmin = −0.55 e Å−3 |
0 restraints |
Experimental. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. |
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 | ||
N1 | 0.3878 (4) | 0.5725 (3) | 0.62065 (16) | 0.0514 (6) | |
H11 | 0.361 (5) | 0.638 (5) | 0.582 (2) | 0.062* | |
H12 | 0.494 (5) | 0.532 (5) | 0.610 (2) | 0.062* | |
C2 | 0.2490 (5) | 0.4279 (4) | 0.61017 (19) | 0.0557 (8) | |
H2A | 0.2421 | 0.3600 | 0.5504 | 0.067* | |
H2B | 0.1318 | 0.4735 | 0.6198 | 0.067* | |
C3 | 0.2949 (4) | 0.3139 (4) | 0.67528 (18) | 0.0471 (7) | |
H3A | 0.2023 | 0.2204 | 0.6683 | 0.057* | |
H3B | 0.4096 | 0.2641 | 0.6642 | 0.057* | |
N4 | 0.3062 (3) | 0.4172 (3) | 0.76485 (13) | 0.0385 (5) | |
C5 | 0.4474 (4) | 0.5584 (3) | 0.77722 (17) | 0.0424 (6) | |
H5A | 0.5640 | 0.5108 | 0.7685 | 0.051* | |
H5B | 0.4531 | 0.6256 | 0.8371 | 0.051* | |
C6 | 0.4075 (4) | 0.6739 (4) | 0.71261 (18) | 0.0470 (7) | |
H6A | 0.2968 | 0.7303 | 0.7252 | 0.056* | |
H6B | 0.5051 | 0.7627 | 0.7193 | 0.056* | |
C21 | 0.3137 (3) | 0.3252 (3) | 0.83448 (17) | 0.0375 (5) | |
C22 | 0.2745 (3) | 0.4102 (3) | 0.91928 (17) | 0.0387 (6) | |
C23 | 0.2796 (4) | 0.3234 (4) | 0.98826 (19) | 0.0470 (6) | |
H23 | 0.2571 | 0.3812 | 1.0443 | 0.056* | |
C24 | 0.3181 (4) | 0.1505 (4) | 0.9745 (2) | 0.0549 (8) | |
H24 | 0.3210 | 0.0927 | 1.0212 | 0.066* | |
C25 | 0.3515 (5) | 0.0658 (4) | 0.8927 (2) | 0.0556 (8) | |
H25 | 0.3747 | −0.0506 | 0.8832 | 0.067* | |
C26 | 0.3511 (4) | 0.1526 (4) | 0.8233 (2) | 0.0473 (7) | |
H26 | 0.3765 | 0.0935 | 0.7680 | 0.057* | |
O22 | 0.2276 (3) | 0.5771 (2) | 0.92653 (12) | 0.0505 (5) | |
C27 | 0.2084 (4) | 0.6742 (4) | 1.01265 (19) | 0.0504 (7) | |
H27A | 0.1755 | 0.7884 | 1.0087 | 0.076* | |
H27B | 0.3209 | 0.6814 | 1.0488 | 0.076* | |
H27C | 0.1156 | 0.6182 | 1.0386 | 0.076* | |
C31 | 0.2104 (4) | 0.8486 (4) | 0.38246 (18) | 0.0423 (6) | |
C32 | 0.1691 (5) | 0.7880 (4) | 0.2931 (2) | 0.0552 (8) | |
H32 | 0.1715 | 0.6704 | 0.2697 | 0.066* | |
C33 | 0.1240 (5) | 0.8992 (4) | 0.2376 (2) | 0.0574 (8) | |
H33 | 0.0956 | 0.8571 | 0.1774 | 0.069* | |
C34 | 0.1217 (4) | 1.0726 (4) | 0.27254 (19) | 0.0457 (6) | |
Br34 | 0.06068 (5) | 1.22764 (5) | 0.19700 (2) | 0.06693 (16) | |
C35 | 0.1596 (6) | 1.1360 (4) | 0.3608 (2) | 0.0713 (11) | |
H35 | 0.1558 | 1.2533 | 0.3841 | 0.086* | |
C36 | 0.2042 (6) | 1.0211 (4) | 0.4153 (2) | 0.0703 (11) | |
H36 | 0.2305 | 1.0633 | 0.4756 | 0.084* | |
C37 | 0.2644 (4) | 0.7278 (4) | 0.4432 (2) | 0.0506 (7) | |
O31 | 0.2859 (5) | 0.7932 (3) | 0.52394 (16) | 0.0910 (10) | |
O32 | 0.2844 (4) | 0.5748 (3) | 0.41048 (16) | 0.0653 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0781 (19) | 0.0471 (14) | 0.0325 (12) | 0.0163 (13) | 0.0077 (12) | 0.0123 (10) |
C2 | 0.080 (2) | 0.0522 (17) | 0.0310 (14) | 0.0068 (15) | −0.0080 (14) | 0.0033 (12) |
C3 | 0.0635 (18) | 0.0421 (15) | 0.0322 (13) | 0.0027 (13) | −0.0021 (12) | 0.0020 (11) |
N4 | 0.0514 (13) | 0.0347 (11) | 0.0269 (10) | 0.0017 (9) | −0.0025 (9) | 0.0031 (8) |
C5 | 0.0555 (16) | 0.0378 (14) | 0.0320 (13) | 0.0012 (12) | 0.0000 (11) | 0.0043 (11) |
C6 | 0.0682 (19) | 0.0364 (14) | 0.0366 (14) | 0.0074 (13) | 0.0075 (13) | 0.0059 (11) |
C21 | 0.0396 (13) | 0.0370 (13) | 0.0347 (13) | 0.0021 (10) | −0.0032 (10) | 0.0077 (10) |
C22 | 0.0404 (13) | 0.0393 (14) | 0.0361 (13) | 0.0049 (11) | 0.0001 (11) | 0.0080 (11) |
C23 | 0.0519 (16) | 0.0534 (16) | 0.0365 (14) | 0.0014 (13) | −0.0001 (12) | 0.0134 (12) |
C24 | 0.0651 (19) | 0.0513 (17) | 0.0516 (18) | −0.0022 (14) | −0.0066 (14) | 0.0251 (14) |
C25 | 0.072 (2) | 0.0348 (14) | 0.059 (2) | 0.0056 (13) | −0.0080 (15) | 0.0128 (13) |
C26 | 0.0577 (17) | 0.0378 (14) | 0.0437 (15) | 0.0041 (12) | −0.0048 (13) | 0.0056 (12) |
O22 | 0.0738 (14) | 0.0445 (11) | 0.0337 (10) | 0.0191 (10) | 0.0067 (9) | 0.0052 (8) |
C27 | 0.0581 (18) | 0.0478 (16) | 0.0412 (15) | 0.0055 (13) | 0.0079 (13) | −0.0025 (12) |
C31 | 0.0473 (15) | 0.0421 (14) | 0.0384 (14) | 0.0069 (11) | 0.0050 (11) | 0.0090 (11) |
C32 | 0.070 (2) | 0.0458 (16) | 0.0469 (17) | 0.0186 (14) | 0.0023 (15) | 0.0005 (13) |
C33 | 0.070 (2) | 0.067 (2) | 0.0331 (15) | 0.0162 (16) | 0.0044 (14) | 0.0033 (14) |
C34 | 0.0459 (15) | 0.0520 (16) | 0.0416 (15) | 0.0018 (12) | −0.0004 (12) | 0.0175 (13) |
Br34 | 0.0726 (2) | 0.0759 (3) | 0.0590 (2) | −0.00290 (17) | −0.00806 (16) | 0.03751 (18) |
C35 | 0.125 (3) | 0.0384 (16) | 0.0471 (18) | 0.0068 (18) | −0.0112 (19) | 0.0089 (14) |
C36 | 0.129 (3) | 0.0435 (17) | 0.0343 (16) | 0.0120 (19) | −0.0120 (18) | 0.0038 (13) |
C37 | 0.0537 (17) | 0.0488 (17) | 0.0534 (18) | 0.0084 (13) | 0.0048 (14) | 0.0190 (14) |
O31 | 0.171 (3) | 0.0586 (15) | 0.0454 (14) | 0.0315 (17) | −0.0072 (16) | 0.0173 (11) |
O32 | 0.0879 (17) | 0.0400 (12) | 0.0704 (15) | 0.0200 (11) | 0.0089 (13) | 0.0127 (10) |
N1—C2 | 1.479 (4) | C24—C25 | 1.361 (5) |
N1—C6 | 1.483 (4) | C24—H24 | 0.9300 |
N1—H11 | 0.89 (4) | C25—C26 | 1.388 (4) |
N1—H12 | 0.88 (4) | C25—H25 | 0.9300 |
C2—C3 | 1.513 (4) | C26—H26 | 0.9300 |
C2—H2A | 0.9700 | O22—C27 | 1.424 (3) |
C2—H2B | 0.9700 | C27—H27A | 0.9600 |
C3—N4 | 1.458 (3) | C27—H27B | 0.9600 |
C3—H3A | 0.9700 | C27—H27C | 0.9600 |
C3—H3B | 0.9700 | C31—C36 | 1.363 (4) |
N4—C21 | 1.418 (3) | C31—C32 | 1.377 (4) |
N4—C5 | 1.470 (4) | C31—C37 | 1.515 (4) |
C5—C6 | 1.508 (4) | C32—C33 | 1.384 (4) |
C5—H5A | 0.9700 | C32—H32 | 0.9300 |
C5—H5B | 0.9700 | C33—C34 | 1.372 (4) |
C6—H6A | 0.9700 | C33—H33 | 0.9300 |
C6—H6B | 0.9700 | C34—C35 | 1.361 (4) |
C21—C26 | 1.387 (4) | C34—Br34 | 1.905 (3) |
C21—C22 | 1.413 (4) | C35—C36 | 1.394 (4) |
C22—O22 | 1.367 (3) | C35—H35 | 0.9300 |
C22—C23 | 1.382 (4) | C36—H36 | 0.9300 |
C23—C24 | 1.390 (4) | C37—O32 | 1.237 (4) |
C23—H23 | 0.9300 | C37—O31 | 1.251 (4) |
C2—N1—C6 | 110.8 (2) | C22—C23—H23 | 119.8 |
C2—N1—H11 | 110 (2) | C24—C23—H23 | 119.8 |
C6—N1—H11 | 112 (2) | C25—C24—C23 | 119.9 (3) |
C2—N1—H12 | 110 (2) | C25—C24—H24 | 120.1 |
C6—N1—H12 | 107 (2) | C23—C24—H24 | 120.1 |
H11—N1—H12 | 106 (3) | C24—C25—C26 | 120.2 (3) |
N1—C2—C3 | 110.6 (2) | C24—C25—H25 | 119.9 |
N1—C2—H2A | 109.5 | C26—C25—H25 | 119.9 |
C3—C2—H2A | 109.5 | C21—C26—C25 | 121.6 (3) |
N1—C2—H2B | 109.5 | C21—C26—H26 | 119.2 |
C3—C2—H2B | 109.5 | C25—C26—H26 | 119.2 |
H2A—C2—H2B | 108.1 | C22—O22—C27 | 117.7 (2) |
N4—C3—C2 | 109.2 (2) | O22—C27—H27A | 109.5 |
N4—C3—H3A | 109.8 | O22—C27—H27B | 109.5 |
C2—C3—H3A | 109.8 | H27A—C27—H27B | 109.5 |
N4—C3—H3B | 109.8 | O22—C27—H27C | 109.5 |
C2—C3—H3B | 109.8 | H27A—C27—H27C | 109.5 |
H3A—C3—H3B | 108.3 | H27B—C27—H27C | 109.5 |
C21—N4—C3 | 116.6 (2) | C36—C31—C32 | 118.4 (3) |
C21—N4—C5 | 113.3 (2) | C36—C31—C37 | 120.4 (3) |
C3—N4—C5 | 110.7 (2) | C32—C31—C37 | 121.2 (3) |
N4—C5—C6 | 110.4 (2) | C31—C32—C33 | 121.0 (3) |
N4—C5—H5A | 109.6 | C31—C32—H32 | 119.5 |
C6—C5—H5A | 109.6 | C33—C32—H32 | 119.5 |
N4—C5—H5B | 109.6 | C34—C33—C32 | 119.1 (3) |
C6—C5—H5B | 109.6 | C34—C33—H33 | 120.4 |
H5A—C5—H5B | 108.1 | C32—C33—H33 | 120.4 |
N1—C6—C5 | 110.7 (2) | C35—C34—C33 | 121.2 (3) |
N1—C6—H6A | 109.5 | C35—C34—Br34 | 119.1 (2) |
C5—C6—H6A | 109.5 | C33—C34—Br34 | 119.7 (2) |
N1—C6—H6B | 109.5 | C34—C35—C36 | 118.5 (3) |
C5—C6—H6B | 109.5 | C34—C35—H35 | 120.7 |
H6A—C6—H6B | 108.1 | C36—C35—H35 | 120.7 |
C26—C21—C22 | 117.5 (2) | C31—C36—C35 | 121.7 (3) |
C26—C21—N4 | 123.4 (2) | C31—C36—H36 | 119.1 |
C22—C21—N4 | 119.0 (2) | C35—C36—H36 | 119.1 |
O22—C22—C23 | 123.8 (2) | O32—C37—O31 | 124.9 (3) |
O22—C22—C21 | 115.9 (2) | O32—C37—C31 | 118.9 (3) |
C23—C22—C21 | 120.3 (2) | O31—C37—C31 | 116.2 (3) |
C22—C23—C24 | 120.5 (3) | ||
C6—N1—C2—C3 | −56.5 (3) | C22—C21—C26—C25 | −0.5 (4) |
N1—C2—C3—N4 | 58.8 (3) | N4—C21—C26—C25 | −177.9 (3) |
C2—C3—N4—C21 | 168.3 (2) | C24—C25—C26—C21 | −1.2 (5) |
C2—C3—N4—C5 | −60.2 (3) | C23—C22—O22—C27 | 9.3 (4) |
C21—N4—C5—C6 | −167.6 (2) | C21—C22—O22—C27 | −172.6 (2) |
C3—N4—C5—C6 | 59.3 (3) | C36—C31—C32—C33 | 0.6 (5) |
C2—N1—C6—C5 | 55.0 (3) | C37—C31—C32—C33 | −178.5 (3) |
N4—C5—C6—N1 | −56.0 (3) | C31—C32—C33—C34 | 0.4 (5) |
C3—N4—C21—C26 | 14.8 (4) | C32—C33—C34—C35 | −1.3 (5) |
C5—N4—C21—C26 | −115.4 (3) | C32—C33—C34—Br34 | 179.8 (2) |
C3—N4—C21—C22 | −162.6 (2) | C33—C34—C35—C36 | 1.1 (6) |
C5—N4—C21—C22 | 67.1 (3) | Br34—C34—C35—C36 | −179.9 (3) |
C26—C21—C22—O22 | −176.2 (2) | C32—C31—C36—C35 | −0.7 (6) |
N4—C21—C22—O22 | 1.4 (4) | C37—C31—C36—C35 | 178.3 (4) |
C26—C21—C22—C23 | 2.0 (4) | C34—C35—C36—C31 | −0.1 (7) |
N4—C21—C22—C23 | 179.6 (2) | C36—C31—C37—O32 | −173.7 (3) |
O22—C22—C23—C24 | 176.1 (3) | C32—C31—C37—O32 | 5.4 (5) |
C21—C22—C23—C24 | −1.9 (4) | C36—C31—C37—O31 | 6.2 (5) |
C22—C23—C24—C25 | 0.2 (5) | C32—C31—C37—O31 | −174.8 (3) |
C23—C24—C25—C26 | 1.4 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H11···O31 | 0.89 (4) | 1.75 (4) | 2.620 (4) | 168 (3) |
N1—H12···O32i | 0.88 (4) | 1.91 (4) | 2.786 (4) | 175 (4) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
C11H17N2O+·C7H4IO2− | Z = 2 |
Mr = 440.27 | F(000) = 440 |
Triclinic, P1 | Dx = 1.609 Mg m−3 |
a = 7.1129 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.2722 (7) Å | Cell parameters from 3897 reflections |
c = 12.5923 (8) Å | θ = 3.0–28.0° |
α = 69.852 (5)° | µ = 1.78 mm−1 |
β = 74.681 (5)° | T = 296 K |
γ = 79.121 (5)° | Needle, orange |
V = 908.82 (10) Å3 | 0.48 × 0.24 × 0.14 mm |
Oxford Diffraction Xcalibur with Sapphire CCD diffractometer | 3897 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 3203 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.012 |
ω scans | θmax = 28.0°, θmin = 3.0° |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | h = −6→9 |
Tmin = 0.534, Tmax = 0.779 | k = −14→14 |
6342 measured reflections | l = −16→16 |
Refinement on F2 | Primary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.026 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.065 | w = 1/[σ2(Fo2) + (0.029P)2 + 0.4404P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.003 |
3897 reflections | Δρmax = 0.52 e Å−3 |
224 parameters | Δρmin = −0.70 e Å−3 |
0 restraints |
Experimental. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. |
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 | ||
N1 | 0.6379 (3) | 0.34876 (17) | 0.41481 (15) | 0.0371 (4) | |
H11 | 0.736 (3) | 0.364 (2) | 0.437 (2) | 0.045* | |
H12 | 0.545 (4) | 0.417 (2) | 0.405 (2) | 0.045* | |
C2 | 0.5540 (3) | 0.2342 (2) | 0.50290 (17) | 0.0393 (4) | |
H2A | 0.4957 | 0.2524 | 0.5752 | 0.047* | |
H2B | 0.6580 | 0.1651 | 0.5168 | 0.047* | |
C3 | 0.4004 (3) | 0.1942 (2) | 0.46316 (17) | 0.0405 (4) | |
H3A | 0.3499 | 0.1181 | 0.5208 | 0.049* | |
H3B | 0.2923 | 0.2609 | 0.4536 | 0.049* | |
N4 | 0.4884 (2) | 0.16937 (15) | 0.35326 (13) | 0.0345 (3) | |
C5 | 0.5578 (3) | 0.2859 (2) | 0.26462 (17) | 0.0414 (5) | |
H5A | 0.4490 | 0.3523 | 0.2555 | 0.050* | |
H5B | 0.6108 | 0.2700 | 0.1909 | 0.050* | |
C6 | 0.7146 (3) | 0.3286 (2) | 0.30021 (18) | 0.0430 (5) | |
H6A | 0.8271 | 0.2646 | 0.3039 | 0.052* | |
H6B | 0.7570 | 0.4071 | 0.2428 | 0.052* | |
C21 | 0.3825 (3) | 0.10145 (18) | 0.31654 (17) | 0.0354 (4) | |
C22 | 0.4854 (3) | 0.0392 (2) | 0.23523 (18) | 0.0420 (5) | |
C23 | 0.3903 (4) | −0.0354 (2) | 0.2031 (2) | 0.0544 (6) | |
H23 | 0.4592 | −0.0769 | 0.1499 | 0.065* | |
C24 | 0.1939 (4) | −0.0483 (2) | 0.2498 (2) | 0.0605 (7) | |
H24 | 0.1313 | −0.0995 | 0.2288 | 0.073* | |
C25 | 0.0906 (4) | 0.0141 (3) | 0.3269 (2) | 0.0594 (7) | |
H25 | −0.0424 | 0.0064 | 0.3570 | 0.071* | |
C26 | 0.1844 (3) | 0.0888 (2) | 0.3602 (2) | 0.0465 (5) | |
H26 | 0.1132 | 0.1309 | 0.4126 | 0.056* | |
O22 | 0.6793 (2) | 0.05587 (18) | 0.19524 (16) | 0.0594 (5) | |
C27 | 0.7839 (4) | 0.0197 (3) | 0.0974 (2) | 0.0694 (8) | |
H27A | 0.9125 | 0.0472 | 0.0736 | 0.104* | |
H27B | 0.7156 | 0.0583 | 0.0354 | 0.104* | |
H27C | 0.7949 | −0.0711 | 0.1166 | 0.104* | |
C31 | 0.9029 (3) | 0.37755 (18) | 0.70670 (17) | 0.0344 (4) | |
C32 | 1.1047 (3) | 0.3626 (2) | 0.69034 (18) | 0.0395 (4) | |
H32 | 1.1812 | 0.3648 | 0.6174 | 0.047* | |
C33 | 1.1957 (3) | 0.3443 (2) | 0.78032 (18) | 0.0411 (5) | |
H33 | 1.3317 | 0.3347 | 0.7681 | 0.049* | |
C34 | 1.0812 (3) | 0.34062 (19) | 0.88832 (17) | 0.0405 (5) | |
I34 | 1.21476 (3) | 0.30958 (2) | 1.02693 (2) | 0.07326 (9) | |
C35 | 0.8796 (4) | 0.3559 (2) | 0.90646 (19) | 0.0528 (6) | |
H35 | 0.8034 | 0.3533 | 0.9795 | 0.063* | |
C36 | 0.7913 (3) | 0.3751 (2) | 0.8158 (2) | 0.0469 (5) | |
H36 | 0.6552 | 0.3865 | 0.8279 | 0.056* | |
C37 | 0.8053 (3) | 0.39540 (18) | 0.60869 (18) | 0.0382 (4) | |
O31 | 0.9072 (2) | 0.36274 (15) | 0.52331 (13) | 0.0466 (3) | |
O32 | 0.6270 (2) | 0.43759 (15) | 0.62045 (15) | 0.0520 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0383 (9) | 0.0379 (9) | 0.0422 (9) | 0.0006 (7) | −0.0142 (7) | −0.0195 (7) |
C2 | 0.0428 (11) | 0.0447 (11) | 0.0327 (10) | −0.0010 (9) | −0.0109 (8) | −0.0150 (8) |
C3 | 0.0397 (11) | 0.0504 (12) | 0.0336 (10) | −0.0068 (9) | −0.0035 (8) | −0.0182 (9) |
N4 | 0.0372 (8) | 0.0381 (9) | 0.0310 (8) | −0.0066 (7) | −0.0049 (7) | −0.0147 (7) |
C5 | 0.0568 (13) | 0.0390 (11) | 0.0309 (10) | −0.0104 (9) | −0.0090 (9) | −0.0118 (8) |
C6 | 0.0477 (12) | 0.0423 (12) | 0.0398 (11) | −0.0116 (9) | −0.0019 (9) | −0.0160 (9) |
C21 | 0.0393 (10) | 0.0338 (10) | 0.0348 (9) | −0.0033 (8) | −0.0131 (8) | −0.0095 (8) |
C22 | 0.0502 (12) | 0.0396 (11) | 0.0415 (11) | −0.0021 (9) | −0.0174 (9) | −0.0151 (9) |
C23 | 0.0783 (17) | 0.0410 (12) | 0.0566 (14) | −0.0021 (11) | −0.0329 (13) | −0.0197 (10) |
C24 | 0.0796 (19) | 0.0472 (14) | 0.0684 (16) | −0.0216 (13) | −0.0396 (15) | −0.0095 (12) |
C25 | 0.0530 (14) | 0.0625 (16) | 0.0630 (15) | −0.0234 (12) | −0.0246 (12) | −0.0021 (12) |
C26 | 0.0418 (12) | 0.0507 (13) | 0.0459 (12) | −0.0068 (10) | −0.0123 (9) | −0.0105 (10) |
O22 | 0.0477 (9) | 0.0821 (12) | 0.0644 (11) | −0.0033 (8) | −0.0030 (8) | −0.0515 (10) |
C27 | 0.0792 (19) | 0.0738 (18) | 0.0601 (16) | −0.0034 (15) | 0.0021 (14) | −0.0420 (14) |
C31 | 0.0364 (10) | 0.0296 (9) | 0.0380 (10) | −0.0024 (8) | −0.0091 (8) | −0.0114 (8) |
C32 | 0.0393 (11) | 0.0443 (11) | 0.0350 (10) | −0.0024 (9) | −0.0068 (8) | −0.0146 (9) |
C33 | 0.0371 (11) | 0.0426 (11) | 0.0443 (11) | −0.0024 (9) | −0.0133 (9) | −0.0121 (9) |
C34 | 0.0551 (13) | 0.0344 (10) | 0.0342 (10) | −0.0054 (9) | −0.0167 (9) | −0.0079 (8) |
I34 | 0.09118 (16) | 0.08904 (16) | 0.04736 (11) | −0.00653 (11) | −0.03522 (9) | −0.01745 (9) |
C35 | 0.0542 (14) | 0.0662 (15) | 0.0340 (11) | −0.0080 (12) | 0.0000 (10) | −0.0171 (10) |
C36 | 0.0369 (11) | 0.0584 (14) | 0.0439 (12) | −0.0037 (10) | −0.0036 (9) | −0.0184 (10) |
C37 | 0.0392 (11) | 0.0319 (10) | 0.0461 (11) | −0.0028 (8) | −0.0159 (9) | −0.0110 (9) |
O31 | 0.0426 (8) | 0.0614 (10) | 0.0433 (8) | −0.0034 (7) | −0.0137 (7) | −0.0232 (7) |
O32 | 0.0399 (8) | 0.0546 (9) | 0.0664 (10) | 0.0106 (7) | −0.0220 (7) | −0.0254 (8) |
N1—C6 | 1.482 (3) | C24—C25 | 1.369 (4) |
N1—C2 | 1.486 (3) | C24—H24 | 0.9300 |
N1—H11 | 0.88 (2) | C25—C26 | 1.391 (3) |
N1—H12 | 0.91 (2) | C25—H25 | 0.9300 |
C2—C3 | 1.510 (3) | C26—H26 | 0.9300 |
C2—H2A | 0.9700 | O22—C27 | 1.409 (3) |
C2—H2B | 0.9700 | C27—H27A | 0.9600 |
C3—N4 | 1.459 (2) | C27—H27B | 0.9600 |
C3—H3A | 0.9700 | C27—H27C | 0.9600 |
C3—H3B | 0.9700 | C31—C32 | 1.381 (3) |
N4—C21 | 1.419 (2) | C31—C36 | 1.387 (3) |
N4—C5 | 1.469 (3) | C31—C37 | 1.508 (3) |
C5—C6 | 1.514 (3) | C32—C33 | 1.386 (3) |
C5—H5A | 0.9700 | C32—H32 | 0.9300 |
C5—H5B | 0.9700 | C33—C34 | 1.379 (3) |
C6—H6A | 0.9700 | C33—H33 | 0.9300 |
C6—H6B | 0.9700 | C34—C35 | 1.378 (3) |
C21—C26 | 1.385 (3) | C34—I34 | 2.098 (2) |
C21—C22 | 1.407 (3) | C35—C36 | 1.379 (3) |
C22—O22 | 1.363 (3) | C35—H35 | 0.9300 |
C22—C23 | 1.387 (3) | C36—H36 | 0.9300 |
C23—C24 | 1.379 (4) | C37—O31 | 1.256 (3) |
C23—H23 | 0.9300 | C37—O32 | 1.256 (2) |
C6—N1—C2 | 111.24 (15) | C24—C23—H23 | 119.9 |
C6—N1—H11 | 108.4 (15) | C22—C23—H23 | 119.9 |
C2—N1—H11 | 108.5 (15) | C25—C24—C23 | 120.2 (2) |
C6—N1—H12 | 106.8 (15) | C25—C24—H24 | 119.9 |
C2—N1—H12 | 110.9 (15) | C23—C24—H24 | 119.9 |
H11—N1—H12 | 111 (2) | C24—C25—C26 | 120.1 (2) |
N1—C2—C3 | 111.04 (16) | C24—C25—H25 | 120.0 |
N1—C2—H2A | 109.4 | C26—C25—H25 | 120.0 |
C3—C2—H2A | 109.4 | C21—C26—C25 | 121.0 (2) |
N1—C2—H2B | 109.4 | C21—C26—H26 | 119.5 |
C3—C2—H2B | 109.4 | C25—C26—H26 | 119.5 |
H2A—C2—H2B | 108.0 | C22—O22—C27 | 119.10 (19) |
N4—C3—C2 | 109.09 (16) | O22—C27—H27A | 109.5 |
N4—C3—H3A | 109.9 | O22—C27—H27B | 109.5 |
C2—C3—H3A | 109.9 | H27A—C27—H27B | 109.5 |
N4—C3—H3B | 109.9 | O22—C27—H27C | 109.5 |
C2—C3—H3B | 109.9 | H27A—C27—H27C | 109.5 |
H3A—C3—H3B | 108.3 | H27B—C27—H27C | 109.5 |
C21—N4—C3 | 117.03 (15) | C32—C31—C36 | 118.49 (19) |
C21—N4—C5 | 114.74 (15) | C32—C31—C37 | 120.99 (18) |
C3—N4—C5 | 109.97 (16) | C36—C31—C37 | 120.52 (18) |
N4—C5—C6 | 109.74 (17) | C31—C32—C33 | 121.39 (19) |
N4—C5—H5A | 109.7 | C31—C32—H32 | 119.3 |
C6—C5—H5A | 109.7 | C33—C32—H32 | 119.3 |
N4—C5—H5B | 109.7 | C34—C33—C32 | 118.95 (19) |
C6—C5—H5B | 109.7 | C34—C33—H33 | 120.5 |
H5A—C5—H5B | 108.2 | C32—C33—H33 | 120.5 |
N1—C6—C5 | 110.39 (17) | C35—C34—C33 | 120.63 (19) |
N1—C6—H6A | 109.6 | C35—C34—I34 | 119.56 (15) |
C5—C6—H6A | 109.6 | C33—C34—I34 | 119.81 (16) |
N1—C6—H6B | 109.6 | C34—C35—C36 | 119.7 (2) |
C5—C6—H6B | 109.6 | C34—C35—H35 | 120.1 |
H6A—C6—H6B | 108.1 | C36—C35—H35 | 120.1 |
C26—C21—C22 | 118.24 (19) | C35—C36—C31 | 120.8 (2) |
C26—C21—N4 | 123.33 (18) | C35—C36—H36 | 119.6 |
C22—C21—N4 | 118.37 (17) | C31—C36—H36 | 119.6 |
O22—C22—C23 | 124.4 (2) | O31—C37—O32 | 125.09 (19) |
O22—C22—C21 | 115.38 (17) | O31—C37—C31 | 117.28 (17) |
C23—C22—C21 | 120.2 (2) | O32—C37—C31 | 117.58 (18) |
C24—C23—C22 | 120.3 (2) | ||
C6—N1—C2—C3 | −54.5 (2) | C22—C21—C26—C25 | 1.6 (3) |
N1—C2—C3—N4 | 58.0 (2) | N4—C21—C26—C25 | −175.6 (2) |
C2—C3—N4—C21 | 164.91 (17) | C24—C25—C26—C21 | −0.1 (4) |
C2—C3—N4—C5 | −61.8 (2) | C23—C22—O22—C27 | 14.5 (4) |
C21—N4—C5—C6 | −163.68 (17) | C21—C22—O22—C27 | −167.1 (2) |
C3—N4—C5—C6 | 61.9 (2) | C36—C31—C32—C33 | 0.6 (3) |
C2—N1—C6—C5 | 53.9 (2) | C37—C31—C32—C33 | −179.05 (19) |
N4—C5—C6—N1 | −57.3 (2) | C31—C32—C33—C34 | 0.2 (3) |
C3—N4—C21—C26 | 18.2 (3) | C32—C33—C34—C35 | −0.5 (3) |
C5—N4—C21—C26 | −112.9 (2) | C32—C33—C34—I34 | 178.83 (15) |
C3—N4—C21—C22 | −159.00 (18) | C33—C34—C35—C36 | 0.0 (4) |
C5—N4—C21—C22 | 69.9 (2) | I34—C34—C35—C36 | −179.37 (18) |
C26—C21—C22—O22 | 179.72 (19) | C34—C35—C36—C31 | 0.9 (4) |
N4—C21—C22—O22 | −2.9 (3) | C32—C31—C36—C35 | −1.1 (3) |
C26—C21—C22—C23 | −1.8 (3) | C37—C31—C36—C35 | 178.5 (2) |
N4—C21—C22—C23 | 175.53 (19) | C32—C31—C37—O31 | 18.7 (3) |
O22—C22—C23—C24 | 178.9 (2) | C36—C31—C37—O31 | −161.0 (2) |
C21—C22—C23—C24 | 0.6 (3) | C32—C31—C37—O32 | −163.71 (19) |
C22—C23—C24—C25 | 1.0 (4) | C36—C31—C37—O32 | 16.7 (3) |
C23—C24—C25—C26 | −1.2 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H11···O31 | 0.88 (2) | 1.83 (2) | 2.684 (3) | 163 (2) |
N1—H11···O32 | 0.88 (2) | 2.60 (2) | 3.060 (3) | 113.6 (17) |
N1—H12···O32i | 0.91 (3) | 1.84 (3) | 2.746 (3) | 176 (3) |
C33—H33···O32ii | 0.93 | 2.57 | 3.327 (3) | 139 |
C2—H2B···Cg2iii | 0.97 | 2.77 | 3.482 (2) | 131 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, y, z; (iii) −x+1, −y, −z+1. |
C11H17N2O+·C7H4FO2− | F(000) = 704 |
Mr = 332.37 | Dx = 1.270 Mg m−3 |
Monoclinic, Cc | Mo Kα radiation, λ = 0.71073 Å |
a = 19.940 (1) Å | Cell parameters from 3343 reflections |
b = 10.2705 (7) Å | θ = 3.0–27.9° |
c = 9.0148 (7) Å | µ = 0.09 mm−1 |
β = 109.663 (8)° | T = 296 K |
V = 1738.5 (2) Å3 | Block, orange |
Z = 4 | 0.48 × 0.36 × 0.22 mm |
Oxford Diffraction Xcalibur with Sapphire CCD diffractometer | 3343 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 2786 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.012 |
ω scans | θmax = 27.9°, θmin = 3.0° |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | h = −25→25 |
Tmin = 0.884, Tmax = 0.963 | k = −13→13 |
6204 measured reflections | l = −11→11 |
Refinement on F2 | H atoms treated by a mixture of independent and constrained refinement |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0593P)2 + 0.1911P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.036 | (Δ/σ)max < 0.001 |
wR(F2) = 0.100 | Δρmax = 0.24 e Å−3 |
S = 1.02 | Δρmin = −0.14 e Å−3 |
3343 reflections | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
256 parameters | Extinction coefficient: 0.0111 (16) |
25 restraints | Absolute structure: Flack x determined using 1089 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
Primary atom site location: difference Fourier map | Absolute structure parameter: 0.2 (3) |
Hydrogen site location: mixed |
Experimental. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. |
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) | |
N1 | 0.40896 (13) | 0.4278 (2) | 0.1329 (3) | 0.0536 (5) | |
H11 | 0.3741 (17) | 0.499 (3) | 0.119 (3) | 0.064* | |
H12 | 0.4026 (16) | 0.383 (3) | 0.046 (4) | 0.064* | |
C2 | 0.39924 (15) | 0.3361 (3) | 0.2509 (3) | 0.0554 (6) | |
H2A | 0.3543 | 0.2906 | 0.2060 | 0.067* | |
H2B | 0.3975 | 0.3846 | 0.3419 | 0.067* | |
C3 | 0.45902 (15) | 0.2383 (3) | 0.3025 (4) | 0.0564 (6) | |
H3A | 0.4530 | 0.1831 | 0.3844 | 0.068* | |
H3B | 0.4579 | 0.1834 | 0.2140 | 0.068* | |
N4 | 0.52785 (12) | 0.30576 (19) | 0.3622 (3) | 0.0482 (5) | |
C5 | 0.53817 (15) | 0.3831 (3) | 0.2368 (3) | 0.0553 (6) | |
H5A | 0.5357 | 0.3275 | 0.1481 | 0.066* | |
H5B | 0.5848 | 0.4237 | 0.2737 | 0.066* | |
C6 | 0.48133 (16) | 0.4861 (3) | 0.1862 (3) | 0.0569 (7) | |
H6A | 0.4861 | 0.5445 | 0.2737 | 0.068* | |
H6B | 0.4877 | 0.5367 | 0.1011 | 0.068* | |
C21 | 0.58610 (13) | 0.2258 (2) | 0.4497 (3) | 0.0476 (6) | |
C22 | 0.58740 (14) | 0.1743 (3) | 0.5946 (3) | 0.0511 (6) | |
C23 | 0.64515 (17) | 0.1007 (3) | 0.6840 (4) | 0.0635 (7) | |
H23 | 0.6453 | 0.0653 | 0.7791 | 0.076* | |
C24 | 0.70234 (17) | 0.0792 (3) | 0.6336 (4) | 0.0702 (8) | |
H24 | 0.7407 | 0.0296 | 0.6946 | 0.084* | |
C25 | 0.70252 (16) | 0.1304 (3) | 0.4950 (4) | 0.0659 (8) | |
H25 | 0.7414 | 0.1168 | 0.4618 | 0.079* | |
C26 | 0.64492 (14) | 0.2029 (3) | 0.4028 (3) | 0.0561 (6) | |
H26 | 0.6455 | 0.2369 | 0.3077 | 0.067* | |
O22 | 0.53102 (11) | 0.2053 (2) | 0.6414 (2) | 0.0672 (6) | |
C27 | 0.5288 (2) | 0.1521 (5) | 0.7843 (5) | 0.1014 (14) | |
H27A | 0.5278 | 0.0588 | 0.7775 | 0.152* | |
H27B | 0.4868 | 0.1822 | 0.8031 | 0.152* | |
H27C | 0.5702 | 0.1791 | 0.8694 | 0.152* | |
C31 | 0.30015 (19) | 0.8223 (3) | 0.2163 (4) | 0.0505 (8) | 0.907 (8) |
C32 | 0.3262 (2) | 0.9222 (4) | 0.3203 (5) | 0.0663 (12) | 0.907 (8) |
F32 | 0.39194 (19) | 0.9110 (3) | 0.4272 (4) | 0.1101 (11) | 0.907 (8) |
C33 | 0.2910 (3) | 1.0368 (4) | 0.3207 (6) | 0.0868 (15) | 0.907 (8) |
H33 | 0.3118 | 1.1029 | 0.3919 | 0.104* | 0.907 (8) |
C34 | 0.2242 (3) | 1.0503 (5) | 0.2129 (6) | 0.0952 (19) | 0.907 (8) |
H34 | 0.1988 | 1.1265 | 0.2108 | 0.114* | 0.907 (8) |
C35 | 0.1943 (3) | 0.9527 (7) | 0.1077 (6) | 0.0984 (19) | 0.907 (8) |
H35 | 0.1487 | 0.9633 | 0.0356 | 0.118* | 0.907 (8) |
C36 | 0.2312 (2) | 0.8384 (5) | 0.1072 (5) | 0.0735 (12) | 0.907 (8) |
H36 | 0.2105 | 0.7728 | 0.0352 | 0.088* | 0.907 (8) |
C37 | 0.34049 (18) | 0.6986 (3) | 0.2127 (4) | 0.0511 (9) | 0.907 (8) |
O31 | 0.3266 (2) | 0.6424 (3) | 0.0810 (3) | 0.0663 (9) | 0.907 (8) |
O32 | 0.38350 (17) | 0.6562 (4) | 0.3377 (4) | 0.0779 (12) | 0.907 (8) |
C41 | 0.2765 (15) | 0.794 (3) | 0.179 (4) | 0.0505 (8) | 0.093 (8) |
C42 | 0.2927 (19) | 0.900 (3) | 0.276 (4) | 0.0663 (12) | 0.093 (8) |
F42 | 0.3612 (19) | 0.929 (4) | 0.357 (6) | 0.1101 (11) | 0.093 (8) |
C43 | 0.248 (2) | 1.005 (4) | 0.262 (6) | 0.0868 (15) | 0.093 (8) |
H43 | 0.2599 | 1.0754 | 0.3298 | 0.104* | 0.093 (8) |
C44 | 0.184 (3) | 0.997 (4) | 0.142 (6) | 0.0952 (19) | 0.093 (8) |
H44 | 0.1518 | 1.0657 | 0.1284 | 0.114* | 0.093 (8) |
C45 | 0.166 (2) | 0.894 (4) | 0.042 (5) | 0.0984 (19) | 0.093 (8) |
H45 | 0.1219 | 0.8954 | −0.0390 | 0.118* | 0.093 (8) |
C46 | 0.2094 (17) | 0.786 (4) | 0.054 (4) | 0.0735 (12) | 0.093 (8) |
H46 | 0.1963 | 0.7151 | −0.0135 | 0.088* | 0.093 (8) |
C47 | 0.3262 (19) | 0.679 (3) | 0.198 (4) | 0.0511 (9) | 0.093 (8) |
O41 | 0.3491 (19) | 0.664 (4) | 0.084 (4) | 0.0663 (9) | 0.093 (8) |
O42 | 0.359 (2) | 0.640 (5) | 0.334 (4) | 0.0779 (12) | 0.093 (8) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0552 (13) | 0.0560 (13) | 0.0418 (11) | 0.0094 (11) | 0.0060 (9) | −0.0028 (9) |
C2 | 0.0443 (13) | 0.0595 (15) | 0.0548 (14) | 0.0023 (12) | 0.0065 (11) | 0.0043 (12) |
C3 | 0.0451 (13) | 0.0491 (14) | 0.0664 (15) | −0.0031 (11) | 0.0074 (11) | 0.0015 (13) |
N4 | 0.0420 (10) | 0.0461 (11) | 0.0512 (11) | −0.0012 (9) | 0.0086 (8) | 0.0033 (9) |
C5 | 0.0546 (15) | 0.0621 (15) | 0.0475 (13) | −0.0023 (13) | 0.0151 (11) | 0.0010 (12) |
C6 | 0.0664 (17) | 0.0532 (15) | 0.0472 (13) | 0.0001 (13) | 0.0139 (12) | 0.0060 (12) |
C21 | 0.0434 (13) | 0.0395 (12) | 0.0529 (13) | 0.0002 (11) | 0.0070 (10) | −0.0050 (11) |
C22 | 0.0458 (13) | 0.0413 (13) | 0.0625 (15) | 0.0009 (10) | 0.0134 (11) | 0.0024 (11) |
C23 | 0.0618 (17) | 0.0523 (15) | 0.0712 (17) | 0.0109 (13) | 0.0154 (13) | 0.0138 (14) |
C24 | 0.0528 (16) | 0.0609 (17) | 0.083 (2) | 0.0184 (14) | 0.0049 (14) | 0.0046 (16) |
C25 | 0.0456 (15) | 0.0724 (19) | 0.0751 (18) | 0.0090 (14) | 0.0142 (13) | −0.0172 (16) |
C26 | 0.0470 (14) | 0.0636 (16) | 0.0541 (14) | 0.0009 (12) | 0.0121 (11) | −0.0126 (13) |
O22 | 0.0646 (12) | 0.0695 (13) | 0.0737 (13) | 0.0176 (10) | 0.0314 (10) | 0.0251 (10) |
C27 | 0.102 (3) | 0.109 (3) | 0.115 (3) | 0.029 (2) | 0.064 (2) | 0.052 (3) |
C31 | 0.0524 (19) | 0.0539 (18) | 0.0516 (18) | 0.0091 (15) | 0.0257 (15) | 0.0149 (15) |
C32 | 0.061 (3) | 0.075 (2) | 0.069 (3) | 0.014 (2) | 0.030 (3) | 0.0084 (19) |
F32 | 0.098 (2) | 0.119 (2) | 0.098 (2) | 0.0153 (17) | 0.0134 (17) | −0.0298 (18) |
C33 | 0.118 (4) | 0.071 (2) | 0.093 (3) | 0.019 (3) | 0.064 (3) | 0.005 (2) |
C34 | 0.121 (5) | 0.089 (3) | 0.100 (4) | 0.052 (3) | 0.069 (4) | 0.040 (3) |
C35 | 0.083 (3) | 0.134 (5) | 0.088 (4) | 0.058 (3) | 0.042 (3) | 0.055 (3) |
C36 | 0.062 (2) | 0.093 (3) | 0.071 (3) | 0.028 (2) | 0.0298 (19) | 0.034 (2) |
C37 | 0.0469 (19) | 0.0538 (18) | 0.0535 (16) | 0.0080 (15) | 0.0180 (13) | 0.0166 (14) |
O31 | 0.064 (2) | 0.0682 (17) | 0.0588 (12) | 0.0137 (15) | 0.0102 (14) | 0.0001 (12) |
O32 | 0.092 (3) | 0.087 (2) | 0.0537 (12) | 0.041 (2) | 0.0226 (16) | 0.0226 (12) |
C41 | 0.0524 (19) | 0.0539 (18) | 0.0516 (18) | 0.0091 (15) | 0.0257 (15) | 0.0149 (15) |
C42 | 0.061 (3) | 0.075 (2) | 0.069 (3) | 0.014 (2) | 0.030 (3) | 0.0084 (19) |
F42 | 0.098 (2) | 0.119 (2) | 0.098 (2) | 0.0153 (17) | 0.0134 (17) | −0.0298 (18) |
C43 | 0.118 (4) | 0.071 (2) | 0.093 (3) | 0.019 (3) | 0.064 (3) | 0.005 (2) |
C44 | 0.121 (5) | 0.089 (3) | 0.100 (4) | 0.052 (3) | 0.069 (4) | 0.040 (3) |
C45 | 0.083 (3) | 0.134 (5) | 0.088 (4) | 0.058 (3) | 0.042 (3) | 0.055 (3) |
C46 | 0.062 (2) | 0.093 (3) | 0.071 (3) | 0.028 (2) | 0.0298 (19) | 0.034 (2) |
C47 | 0.0469 (19) | 0.0538 (18) | 0.0535 (16) | 0.0080 (15) | 0.0180 (13) | 0.0166 (14) |
O41 | 0.064 (2) | 0.0682 (17) | 0.0588 (12) | 0.0137 (15) | 0.0102 (14) | 0.0001 (12) |
O42 | 0.092 (3) | 0.087 (2) | 0.0537 (12) | 0.041 (2) | 0.0226 (16) | 0.0226 (12) |
N1—C2 | 1.482 (4) | C27—H27B | 0.9600 |
N1—C6 | 1.485 (4) | C27—H27C | 0.9600 |
N1—H11 | 0.98 (3) | C31—C32 | 1.369 (6) |
N1—H12 | 0.88 (4) | C31—C36 | 1.405 (5) |
C2—C3 | 1.508 (4) | C31—C37 | 1.510 (4) |
C2—H2A | 0.9700 | C32—F32 | 1.345 (5) |
C2—H2B | 0.9700 | C32—C33 | 1.371 (5) |
C3—N4 | 1.468 (3) | C33—C34 | 1.366 (7) |
C3—H3A | 0.9700 | C33—H33 | 0.9300 |
C3—H3B | 0.9700 | C34—C35 | 1.370 (8) |
N4—C21 | 1.424 (3) | C34—H34 | 0.9300 |
N4—C5 | 1.452 (3) | C35—C36 | 1.387 (7) |
C5—C6 | 1.504 (4) | C35—H35 | 0.9300 |
C5—H5A | 0.9700 | C36—H36 | 0.9300 |
C5—H5B | 0.9700 | C37—O32 | 1.243 (3) |
C6—H6A | 0.9700 | C37—O31 | 1.264 (4) |
C6—H6B | 0.9700 | C41—C42 | 1.365 (13) |
C21—C26 | 1.394 (4) | C41—C46 | 1.432 (13) |
C21—C22 | 1.402 (4) | C41—C47 | 1.518 (12) |
C22—O22 | 1.365 (3) | C42—F42 | 1.347 (14) |
C22—C23 | 1.387 (4) | C42—C43 | 1.376 (13) |
C23—C24 | 1.380 (5) | C43—C44 | 1.364 (15) |
C23—H23 | 0.9300 | C43—H43 | 0.9300 |
C24—C25 | 1.357 (5) | C44—C45 | 1.365 (15) |
C24—H24 | 0.9300 | C44—H44 | 0.9300 |
C25—C26 | 1.386 (4) | C45—C46 | 1.388 (14) |
C25—H25 | 0.9300 | C45—H45 | 0.9300 |
C26—H26 | 0.9300 | C46—H46 | 0.9300 |
O22—C27 | 1.414 (4) | C47—O42 | 1.245 (13) |
C27—H27A | 0.9600 | C47—O41 | 1.263 (13) |
C2—N1—C6 | 111.80 (18) | C21—C26—H26 | 119.3 |
C2—N1—H11 | 107.6 (17) | C22—O22—C27 | 118.3 (2) |
C6—N1—H11 | 108.1 (18) | O22—C27—H27A | 109.5 |
C2—N1—H12 | 107 (2) | O22—C27—H27B | 109.5 |
C6—N1—H12 | 109 (2) | H27A—C27—H27B | 109.5 |
H11—N1—H12 | 113 (3) | O22—C27—H27C | 109.5 |
N1—C2—C3 | 111.3 (2) | H27A—C27—H27C | 109.5 |
N1—C2—H2A | 109.4 | H27B—C27—H27C | 109.5 |
C3—C2—H2A | 109.4 | C32—C31—C36 | 116.6 (3) |
N1—C2—H2B | 109.4 | C32—C31—C37 | 124.3 (3) |
C3—C2—H2B | 109.4 | C36—C31—C37 | 119.1 (3) |
H2A—C2—H2B | 108.0 | F32—C32—C31 | 118.7 (3) |
N4—C3—C2 | 110.1 (2) | F32—C32—C33 | 116.6 (4) |
N4—C3—H3A | 109.6 | C31—C32—C33 | 124.7 (4) |
C2—C3—H3A | 109.6 | C34—C33—C32 | 117.5 (5) |
N4—C3—H3B | 109.6 | C34—C33—H33 | 121.2 |
C2—C3—H3B | 109.6 | C32—C33—H33 | 121.2 |
H3A—C3—H3B | 108.2 | C33—C34—C35 | 120.8 (4) |
C21—N4—C5 | 116.3 (2) | C33—C34—H34 | 119.6 |
C21—N4—C3 | 114.73 (19) | C35—C34—H34 | 119.6 |
C5—N4—C3 | 109.4 (2) | C34—C35—C36 | 120.9 (4) |
N4—C5—C6 | 109.3 (2) | C34—C35—H35 | 119.6 |
N4—C5—H5A | 109.8 | C36—C35—H35 | 119.6 |
C6—C5—H5A | 109.8 | C35—C36—C31 | 119.5 (5) |
N4—C5—H5B | 109.8 | C35—C36—H36 | 120.2 |
C6—C5—H5B | 109.8 | C31—C36—H36 | 120.2 |
H5A—C5—H5B | 108.3 | O32—C37—O31 | 123.9 (3) |
N1—C6—C5 | 111.5 (2) | O32—C37—C31 | 119.0 (3) |
N1—C6—H6A | 109.3 | O31—C37—C31 | 117.0 (3) |
C5—C6—H6A | 109.3 | C42—C41—C46 | 120.5 (14) |
N1—C6—H6B | 109.3 | C42—C41—C47 | 123.0 (16) |
C5—C6—H6B | 109.3 | C46—C41—C47 | 116.5 (15) |
H6A—C6—H6B | 108.0 | F42—C42—C41 | 120.1 (19) |
C26—C21—C22 | 117.7 (2) | F42—C42—C43 | 113 (2) |
C26—C21—N4 | 122.8 (2) | C41—C42—C43 | 123.7 (16) |
C22—C21—N4 | 119.3 (2) | C44—C43—C42 | 115.8 (17) |
O22—C22—C23 | 123.8 (3) | C44—C43—H43 | 122.1 |
O22—C22—C21 | 116.2 (2) | C42—C43—H43 | 122.1 |
C23—C22—C21 | 119.9 (2) | C43—C44—C45 | 122.5 (17) |
C24—C23—C22 | 120.8 (3) | C43—C44—H44 | 118.8 |
C24—C23—H23 | 119.6 | C45—C44—H44 | 118.8 |
C22—C23—H23 | 119.6 | C44—C45—C46 | 123.1 (17) |
C25—C24—C23 | 120.0 (3) | C44—C45—H45 | 118.4 |
C25—C24—H24 | 120.0 | C46—C45—H45 | 118.4 |
C23—C24—H24 | 120.0 | C45—C46—C41 | 114.4 (16) |
C24—C25—C26 | 120.1 (3) | C45—C46—H46 | 122.8 |
C24—C25—H25 | 119.9 | C41—C46—H46 | 122.8 |
C26—C25—H25 | 119.9 | O42—C47—O41 | 123 (2) |
C25—C26—C21 | 121.4 (3) | O42—C47—C41 | 118.2 (19) |
C25—C26—H26 | 119.3 | O41—C47—C41 | 113.7 (19) |
C6—N1—C2—C3 | −50.7 (3) | C37—C31—C32—C33 | 177.5 (3) |
N1—C2—C3—N4 | 55.7 (3) | F32—C32—C33—C34 | 179.8 (4) |
C2—C3—N4—C21 | 165.0 (2) | C31—C32—C33—C34 | 2.2 (6) |
C2—C3—N4—C5 | −62.2 (3) | C32—C33—C34—C35 | −0.6 (6) |
C21—N4—C5—C6 | −165.1 (2) | C33—C34—C35—C36 | −0.5 (7) |
C3—N4—C5—C6 | 62.9 (3) | C34—C35—C36—C31 | 0.1 (6) |
C2—N1—C6—C5 | 51.9 (3) | C32—C31—C36—C35 | 1.3 (5) |
N4—C5—C6—N1 | −57.9 (3) | C37—C31—C36—C35 | −178.8 (4) |
C5—N4—C21—C26 | −11.4 (3) | C32—C31—C37—O32 | 31.1 (5) |
C3—N4—C21—C26 | 118.2 (3) | C36—C31—C37—O32 | −148.9 (4) |
C5—N4—C21—C22 | 164.2 (2) | C32—C31—C37—O31 | −150.8 (4) |
C3—N4—C21—C22 | −66.3 (3) | C36—C31—C37—O31 | 29.3 (5) |
C26—C21—C22—O22 | 176.1 (2) | C46—C41—C42—F42 | −159 (5) |
N4—C21—C22—O22 | 0.3 (3) | C47—C41—C42—F42 | 23 (6) |
C26—C21—C22—C23 | −1.6 (3) | C46—C41—C42—C43 | 0 (6) |
N4—C21—C22—C23 | −177.4 (2) | C47—C41—C42—C43 | −179 (4) |
O22—C22—C23—C24 | −176.3 (3) | F42—C42—C43—C44 | 160 (5) |
C21—C22—C23—C24 | 1.3 (4) | C41—C42—C43—C44 | 0 (7) |
C22—C23—C24—C25 | 0.0 (5) | C42—C43—C44—C45 | 0 (8) |
C23—C24—C25—C26 | −0.9 (4) | C43—C44—C45—C46 | 1 (9) |
C24—C25—C26—C21 | 0.5 (4) | C44—C45—C46—C41 | −2 (7) |
C22—C21—C26—C25 | 0.8 (4) | C42—C41—C46—C45 | 1 (6) |
N4—C21—C26—C25 | 176.4 (2) | C47—C41—C46—C45 | 180 (4) |
C23—C22—O22—C27 | −4.5 (5) | C42—C41—C47—O42 | 40 (6) |
C21—C22—O22—C27 | 177.9 (3) | C46—C41—C47—O42 | −138 (5) |
C36—C31—C32—F32 | 179.9 (4) | C42—C41—C47—O41 | −115 (4) |
C37—C31—C32—F32 | 0.0 (5) | C46—C41—C47—O41 | 66 (5) |
C36—C31—C32—C33 | −2.6 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H11···O31 | 0.99 (3) | 1.72 (3) | 2.694 (4) | 167 (3) |
N1—H11···O32 | 0.99 (3) | 2.51 (3) | 3.131 (4) | 120.9 (19) |
N1—H12···O32i | 0.88 (3) | 1.83 (3) | 2.679 (4) | 161 (3) |
N1—H11···O41 | 0.99 (3) | 1.77 (5) | 2.67 (4) | 151 (3) |
N1—H11···O42 | 0.99 (3) | 2.52 (5) | 3.20 (4) | 126 (2) |
N1—H12···O42i | 0.88 (3) | 1.83 (5) | 2.63 (4) | 151 (3) |
C34—H34···Cg2ii | 0.93 | 2.74 | 3.543 (5) | 145 |
C44—H44···Cg2ii | 0.93 | 2.99 | 3.73 (4) | 137 |
C26—H26···Cg3iii | 0.93 | 2.96 | 3.754 (17) | 144 |
Symmetry codes: (i) x, −y+1, z−1/2; (ii) x−1/2, −y+3/2, z−1/2; (iii) x+1/2, y−1/2, z. |
C11H17N2O+·C7H4ClO2− | F(000) = 736 |
Mr = 348.82 | Dx = 1.272 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 7.9974 (8) Å | Cell parameters from 4043 reflections |
b = 27.611 (2) Å | θ = 2.6–28.0° |
c = 8.5972 (9) Å | µ = 0.23 mm−1 |
β = 106.40 (1)° | T = 296 K |
V = 1821.2 (3) Å3 | Needle, orange |
Z = 4 | 0.48 × 0.20 × 0.12 mm |
Oxford Diffraction Xcalibur with Sapphire CCD diffractometer | 3410 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 2060 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
ω scans | θmax = 25.6°, θmin = 2.6° |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | h = −9→9 |
Tmin = 0.747, Tmax = 0.973 | k = −33→33 |
13275 measured reflections | l = −10→10 |
Refinement on F2 | Primary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.067 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.216 | w = 1/[σ2(Fo2) + (0.1138P)2 + 0.7483P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
3410 reflections | Δρmax = 1.15 e Å−3 |
223 parameters | Δρmin = −0.29 e Å−3 |
0 restraints |
Experimental. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. |
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 | ||
N1 | 0.4620 (4) | 0.44249 (11) | 0.3578 (4) | 0.0640 (8) | |
H11 | 0.368 (5) | 0.4525 (14) | 0.402 (4) | 0.077* | |
H12 | 0.511 (5) | 0.4709 (16) | 0.336 (4) | 0.077* | |
C2 | 0.3954 (4) | 0.41253 (14) | 0.2112 (5) | 0.0684 (10) | |
H2A | 0.3246 | 0.4323 | 0.1241 | 0.082* | |
H2B | 0.3225 | 0.3869 | 0.2333 | 0.082* | |
C3 | 0.5449 (4) | 0.39067 (13) | 0.1593 (4) | 0.0614 (9) | |
H3A | 0.4993 | 0.3699 | 0.0659 | 0.074* | |
H3B | 0.6122 | 0.4163 | 0.1284 | 0.074* | |
N4 | 0.6572 (3) | 0.36247 (10) | 0.2916 (3) | 0.0545 (7) | |
C5 | 0.7325 (5) | 0.39472 (14) | 0.4289 (4) | 0.0666 (10) | |
H5A | 0.7975 | 0.4204 | 0.3957 | 0.080* | |
H5B | 0.8118 | 0.3767 | 0.5159 | 0.080* | |
C6 | 0.5886 (5) | 0.41589 (16) | 0.4871 (5) | 0.0747 (11) | |
H6A | 0.5290 | 0.3901 | 0.5265 | 0.090* | |
H6B | 0.6379 | 0.4377 | 0.5769 | 0.090* | |
C21 | 0.7769 (4) | 0.33160 (12) | 0.2452 (4) | 0.0538 (8) | |
C22 | 0.7097 (5) | 0.29139 (12) | 0.1470 (4) | 0.0607 (9) | |
C23 | 0.8208 (7) | 0.26032 (14) | 0.0999 (5) | 0.0798 (12) | |
H23 | 0.7765 | 0.2342 | 0.0326 | 0.096* | |
C24 | 1.0003 (7) | 0.26825 (19) | 0.1536 (6) | 0.0962 (16) | |
H24 | 1.0751 | 0.2470 | 0.1223 | 0.115* | |
C25 | 1.0676 (6) | 0.30630 (18) | 0.2506 (6) | 0.0869 (13) | |
H25 | 1.1875 | 0.3109 | 0.2868 | 0.104* | |
C26 | 0.9558 (5) | 0.33835 (14) | 0.2954 (4) | 0.0672 (10) | |
H26 | 1.0018 | 0.3648 | 0.3602 | 0.081* | |
O22 | 0.5338 (3) | 0.28580 (9) | 0.1060 (3) | 0.0770 (8) | |
C27 | 0.4570 (7) | 0.24698 (17) | 0.0025 (6) | 0.1036 (16) | |
H27A | 0.3330 | 0.2476 | −0.0157 | 0.155* | |
H27B | 0.4835 | 0.2502 | −0.0992 | 0.155* | |
H27C | 0.5027 | 0.2168 | 0.0522 | 0.155* | |
C31 | 0.1308 (4) | 0.43466 (12) | 0.7353 (4) | 0.0541 (8) | |
C32 | 0.1418 (4) | 0.38566 (13) | 0.7729 (4) | 0.0606 (9) | |
Cl32 | 0.29281 (16) | 0.35006 (4) | 0.71550 (13) | 0.0871 (4) | |
C33 | 0.0387 (6) | 0.36423 (19) | 0.8551 (5) | 0.0886 (13) | |
H33 | 0.0482 | 0.3312 | 0.8774 | 0.106* | |
C34 | −0.0776 (7) | 0.3916 (3) | 0.9036 (6) | 0.1056 (17) | |
H34 | −0.1480 | 0.3772 | 0.9600 | 0.127* | |
C35 | −0.0935 (6) | 0.4406 (2) | 0.8710 (5) | 0.0955 (15) | |
H35 | −0.1735 | 0.4591 | 0.9055 | 0.115* | |
C36 | 0.0107 (5) | 0.46182 (16) | 0.7865 (5) | 0.0760 (11) | |
H36 | 0.0000 | 0.4948 | 0.7637 | 0.091* | |
C37 | 0.2417 (5) | 0.45733 (12) | 0.6402 (5) | 0.0643 (9) | |
O31 | 0.1985 (3) | 0.45110 (11) | 0.4917 (3) | 0.0810 (8) | |
O32 | 0.3701 (5) | 0.48041 (13) | 0.7200 (4) | 0.1152 (12) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0672 (19) | 0.0561 (18) | 0.075 (2) | −0.0144 (15) | 0.0306 (17) | −0.0193 (16) |
C2 | 0.058 (2) | 0.067 (2) | 0.075 (2) | −0.0070 (17) | 0.0105 (18) | −0.0203 (19) |
C3 | 0.063 (2) | 0.065 (2) | 0.051 (2) | 0.0015 (17) | 0.0071 (16) | −0.0152 (16) |
N4 | 0.0560 (16) | 0.0569 (16) | 0.0480 (15) | −0.0057 (12) | 0.0104 (13) | −0.0120 (12) |
C5 | 0.066 (2) | 0.073 (2) | 0.055 (2) | −0.0103 (18) | 0.0071 (17) | −0.0133 (17) |
C6 | 0.084 (3) | 0.083 (3) | 0.058 (2) | −0.012 (2) | 0.022 (2) | −0.024 (2) |
C21 | 0.060 (2) | 0.0538 (18) | 0.0486 (18) | −0.0018 (15) | 0.0169 (15) | 0.0073 (15) |
C22 | 0.079 (2) | 0.0516 (19) | 0.057 (2) | 0.0033 (18) | 0.0281 (18) | 0.0030 (16) |
C23 | 0.113 (4) | 0.056 (2) | 0.082 (3) | 0.013 (2) | 0.045 (3) | 0.0067 (19) |
C24 | 0.113 (4) | 0.080 (3) | 0.114 (4) | 0.045 (3) | 0.062 (3) | 0.038 (3) |
C25 | 0.072 (3) | 0.084 (3) | 0.108 (3) | 0.025 (2) | 0.029 (2) | 0.042 (3) |
C26 | 0.061 (2) | 0.067 (2) | 0.067 (2) | 0.0059 (18) | 0.0090 (18) | 0.0218 (18) |
O22 | 0.0822 (18) | 0.0675 (16) | 0.0825 (18) | −0.0186 (13) | 0.0251 (14) | −0.0303 (14) |
C27 | 0.129 (4) | 0.072 (3) | 0.111 (4) | −0.036 (3) | 0.037 (3) | −0.041 (3) |
C31 | 0.0585 (19) | 0.0577 (19) | 0.0435 (17) | −0.0075 (15) | 0.0100 (15) | 0.0004 (14) |
C32 | 0.072 (2) | 0.062 (2) | 0.0431 (18) | −0.0134 (17) | 0.0088 (16) | 0.0058 (15) |
Cl32 | 0.1206 (9) | 0.0538 (6) | 0.0861 (8) | 0.0079 (5) | 0.0279 (6) | 0.0040 (5) |
C33 | 0.109 (4) | 0.092 (3) | 0.065 (3) | −0.020 (3) | 0.026 (3) | 0.020 (2) |
C34 | 0.103 (4) | 0.151 (5) | 0.070 (3) | −0.021 (4) | 0.036 (3) | 0.033 (3) |
C35 | 0.080 (3) | 0.148 (5) | 0.064 (3) | 0.012 (3) | 0.031 (2) | 0.007 (3) |
C36 | 0.076 (2) | 0.086 (3) | 0.069 (2) | 0.007 (2) | 0.025 (2) | 0.004 (2) |
C37 | 0.072 (2) | 0.0407 (17) | 0.085 (3) | −0.0034 (17) | 0.030 (2) | 0.0005 (18) |
O31 | 0.0823 (18) | 0.101 (2) | 0.0683 (18) | 0.0104 (15) | 0.0350 (15) | 0.0168 (15) |
O32 | 0.130 (3) | 0.094 (2) | 0.132 (3) | −0.062 (2) | 0.053 (2) | −0.024 (2) |
N1—C6 | 1.472 (5) | C24—C25 | 1.355 (7) |
N1—C2 | 1.475 (4) | C24—H24 | 0.9300 |
N1—H11 | 0.97 (4) | C25—C26 | 1.387 (6) |
N1—H12 | 0.92 (4) | C25—H25 | 0.9300 |
C2—C3 | 1.515 (5) | C26—H26 | 0.9300 |
C2—H2A | 0.9700 | O22—C27 | 1.418 (4) |
C2—H2B | 0.9700 | C27—H27A | 0.9600 |
C3—N4 | 1.460 (4) | C27—H27B | 0.9600 |
C3—H3A | 0.9700 | C27—H27C | 0.9600 |
C3—H3B | 0.9700 | C31—C36 | 1.385 (5) |
N4—C21 | 1.421 (4) | C31—C32 | 1.388 (5) |
N4—C5 | 1.465 (4) | C31—C37 | 1.503 (5) |
C5—C6 | 1.497 (5) | C32—C33 | 1.363 (5) |
C5—H5A | 0.9700 | C32—Cl32 | 1.733 (4) |
C5—H5B | 0.9700 | C33—C34 | 1.354 (7) |
C6—H6A | 0.9700 | C33—H33 | 0.9300 |
C6—H6B | 0.9700 | C34—C35 | 1.378 (7) |
C21—C26 | 1.385 (5) | C34—H34 | 0.9300 |
C21—C22 | 1.407 (5) | C35—C36 | 1.381 (6) |
C22—O22 | 1.359 (4) | C35—H35 | 0.9300 |
C22—C23 | 1.375 (5) | C36—H36 | 0.9300 |
C23—C24 | 1.395 (6) | C37—O31 | 1.237 (5) |
C23—H23 | 0.9300 | C37—O32 | 1.238 (5) |
C6—N1—C2 | 111.8 (3) | C22—C23—H23 | 120.2 |
C6—N1—H11 | 107 (2) | C24—C23—H23 | 120.2 |
C2—N1—H11 | 111 (2) | C25—C24—C23 | 121.2 (4) |
C6—N1—H12 | 110 (2) | C25—C24—H24 | 119.4 |
C2—N1—H12 | 112 (2) | C23—C24—H24 | 119.4 |
H11—N1—H12 | 105 (3) | C24—C25—C26 | 119.4 (4) |
N1—C2—C3 | 110.5 (3) | C24—C25—H25 | 120.3 |
N1—C2—H2A | 109.5 | C26—C25—H25 | 120.3 |
C3—C2—H2A | 109.5 | C21—C26—C25 | 121.2 (4) |
N1—C2—H2B | 109.5 | C21—C26—H26 | 119.4 |
C3—C2—H2B | 109.5 | C25—C26—H26 | 119.4 |
H2A—C2—H2B | 108.1 | C22—O22—C27 | 118.8 (3) |
N4—C3—C2 | 110.3 (3) | O22—C27—H27A | 109.5 |
N4—C3—H3A | 109.6 | O22—C27—H27B | 109.5 |
C2—C3—H3A | 109.6 | H27A—C27—H27B | 109.5 |
N4—C3—H3B | 109.6 | O22—C27—H27C | 109.5 |
C2—C3—H3B | 109.6 | H27A—C27—H27C | 109.5 |
H3A—C3—H3B | 108.1 | H27B—C27—H27C | 109.5 |
C21—N4—C3 | 114.6 (2) | C36—C31—C32 | 117.3 (3) |
C21—N4—C5 | 115.8 (3) | C36—C31—C37 | 121.1 (3) |
C3—N4—C5 | 109.0 (3) | C32—C31—C37 | 121.6 (3) |
N4—C5—C6 | 109.1 (3) | C33—C32—C31 | 122.4 (4) |
N4—C5—H5A | 109.9 | C33—C32—Cl32 | 118.2 (3) |
C6—C5—H5A | 109.9 | C31—C32—Cl32 | 119.4 (3) |
N4—C5—H5B | 109.9 | C34—C33—C32 | 119.1 (5) |
C6—C5—H5B | 109.9 | C34—C33—H33 | 120.5 |
H5A—C5—H5B | 108.3 | C32—C33—H33 | 120.5 |
N1—C6—C5 | 111.8 (3) | C33—C34—C35 | 121.1 (4) |
N1—C6—H6A | 109.2 | C33—C34—H34 | 119.4 |
C5—C6—H6A | 109.2 | C35—C34—H34 | 119.4 |
N1—C6—H6B | 109.2 | C34—C35—C36 | 119.3 (4) |
C5—C6—H6B | 109.2 | C34—C35—H35 | 120.4 |
H6A—C6—H6B | 107.9 | C36—C35—H35 | 120.4 |
C26—C21—C22 | 118.6 (3) | C35—C36—C31 | 120.8 (4) |
C26—C21—N4 | 123.4 (3) | C35—C36—H36 | 119.6 |
C22—C21—N4 | 118.0 (3) | C31—C36—H36 | 119.6 |
O22—C22—C23 | 124.1 (4) | O31—C37—O32 | 126.2 (4) |
O22—C22—C21 | 115.9 (3) | O31—C37—C31 | 117.9 (3) |
C23—C22—C21 | 120.0 (4) | O32—C37—C31 | 115.9 (4) |
C22—C23—C24 | 119.6 (4) | ||
C6—N1—C2—C3 | −51.8 (4) | C22—C21—C26—C25 | −0.1 (5) |
N1—C2—C3—N4 | 56.7 (4) | N4—C21—C26—C25 | 178.0 (3) |
C2—C3—N4—C21 | 166.2 (3) | C24—C25—C26—C21 | 1.3 (6) |
C2—C3—N4—C5 | −62.2 (3) | C23—C22—O22—C27 | −2.9 (5) |
C21—N4—C5—C6 | −166.8 (3) | C21—C22—O22—C27 | 177.8 (3) |
C3—N4—C5—C6 | 62.2 (4) | C36—C31—C32—C33 | 0.7 (5) |
C2—N1—C6—C5 | 53.2 (4) | C37—C31—C32—C33 | −178.1 (4) |
N4—C5—C6—N1 | −58.0 (4) | C36—C31—C32—Cl32 | −178.7 (3) |
C3—N4—C21—C26 | 112.9 (3) | C37—C31—C32—Cl32 | 2.4 (4) |
C5—N4—C21—C26 | −15.3 (4) | C31—C32—C33—C34 | −0.7 (6) |
C3—N4—C21—C22 | −68.9 (4) | Cl32—C32—C33—C34 | 178.7 (3) |
C5—N4—C21—C22 | 162.8 (3) | C32—C33—C34—C35 | 0.2 (7) |
C26—C21—C22—O22 | 177.9 (3) | C33—C34—C35—C36 | 0.3 (7) |
N4—C21—C22—O22 | −0.3 (4) | C34—C35—C36—C31 | −0.3 (6) |
C26—C21—C22—C23 | −1.4 (5) | C32—C31—C36—C35 | −0.2 (5) |
N4—C21—C22—C23 | −179.6 (3) | C37—C31—C36—C35 | 178.6 (4) |
O22—C22—C23—C24 | −177.6 (4) | C36—C31—C37—O31 | −101.0 (4) |
C21—C22—C23—C24 | 1.7 (5) | C32—C31—C37—O31 | 77.8 (4) |
C22—C23—C24—C25 | −0.5 (6) | C36—C31—C37—O32 | 79.5 (4) |
C23—C24—C25—C26 | −0.9 (6) | C32—C31—C37—O32 | −101.7 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H11···O31 | 0.97 (4) | 1.74 (3) | 2.682 (4) | 162 (3) |
N1—H12···O32i | 0.92 (4) | 1.79 (4) | 2.700 (5) | 170 (4) |
C5—H5B···Cg1ii | 0.97 | 2.87 | 3.554 (4) | 128 |
C34—H34···Cg2iii | 0.93 | 2.93 | 3.658 (7) | 136 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, y, z; (iii) x−1, y, z+1. |
C11H17N2O+·C7H4BrO2− | Dx = 1.451 Mg m−3 |
Mr = 393.28 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 3863 reflections |
a = 6.9824 (2) Å | θ = 5.6–89.3° |
b = 13.2292 (4) Å | µ = 2.30 mm−1 |
c = 19.4903 (7) Å | T = 293 K |
V = 1800.35 (10) Å3 | Block, orange |
Z = 4 | 0.50 × 0.50 × 0.48 mm |
F(000) = 808 |
Oxford Diffraction Xcalibur with Sapphire CCD diffractometer | 3895 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 2640 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
ω scans | θmax = 27.7°, θmin = 2.6° |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | h = −9→9 |
Tmin = 0.297, Tmax = 0.331 | k = −16→17 |
13089 measured reflections | l = −24→23 |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.035 | w = 1/[σ2(Fo2) + (0.0418P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.077 | (Δ/σ)max = 0.001 |
S = 0.94 | Δρmax = 0.28 e Å−3 |
3895 reflections | Δρmin = −0.53 e Å−3 |
224 parameters | Absolute structure: Flack x determined using 919 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
0 restraints | Absolute structure parameter: 0.004 (5) |
Primary atom site location: difference Fourier map |
Experimental. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. |
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 | ||
N1 | 0.2366 (5) | 0.3584 (2) | 0.50360 (15) | 0.0385 (7) | |
H11 | 0.156 (5) | 0.338 (3) | 0.5251 (19) | 0.046* | |
H12 | 0.271 (5) | 0.307 (2) | 0.4774 (17) | 0.046* | |
C2 | 0.4021 (5) | 0.3893 (3) | 0.54630 (18) | 0.0422 (9) | |
H2A | 0.4540 | 0.3309 | 0.5699 | 0.051* | |
H2B | 0.3611 | 0.4380 | 0.5805 | 0.051* | |
C3 | 0.5535 (5) | 0.4355 (2) | 0.50113 (17) | 0.0351 (8) | |
H3A | 0.6611 | 0.4572 | 0.5290 | 0.042* | |
H3B | 0.5993 | 0.3855 | 0.4686 | 0.042* | |
N4 | 0.4745 (4) | 0.52259 (19) | 0.46388 (14) | 0.0323 (7) | |
C5 | 0.3155 (5) | 0.4908 (2) | 0.42030 (18) | 0.0356 (9) | |
H5A | 0.3607 | 0.4421 | 0.3868 | 0.043* | |
H5B | 0.2651 | 0.5488 | 0.3957 | 0.043* | |
C6 | 0.1594 (5) | 0.4441 (3) | 0.4630 (2) | 0.0446 (10) | |
H6A | 0.1064 | 0.4946 | 0.4938 | 0.054* | |
H6B | 0.0574 | 0.4203 | 0.4334 | 0.054* | |
C21 | 0.6096 (5) | 0.5876 (2) | 0.43291 (17) | 0.0318 (8) | |
C22 | 0.7393 (5) | 0.6421 (2) | 0.47504 (16) | 0.0353 (7) | |
C23 | 0.8583 (5) | 0.7139 (3) | 0.4459 (2) | 0.0493 (10) | |
H23 | 0.9422 | 0.7502 | 0.4735 | 0.059* | |
C24 | 0.8539 (6) | 0.7323 (3) | 0.3762 (2) | 0.0574 (11) | |
H24 | 0.9346 | 0.7808 | 0.3573 | 0.069* | |
C25 | 0.7323 (5) | 0.6800 (3) | 0.33479 (18) | 0.0482 (9) | |
H25 | 0.7286 | 0.6931 | 0.2879 | 0.058* | |
C26 | 0.6140 (5) | 0.6070 (3) | 0.36316 (18) | 0.0392 (9) | |
H26 | 0.5348 | 0.5698 | 0.3343 | 0.047* | |
O22 | 0.7279 (4) | 0.62323 (15) | 0.54385 (11) | 0.0412 (6) | |
C27 | 0.8382 (6) | 0.6854 (3) | 0.58800 (19) | 0.0531 (11) | |
H27A | 0.9718 | 0.6758 | 0.5784 | 0.080* | |
H27B | 0.8126 | 0.6675 | 0.6348 | 0.080* | |
H27C | 0.8048 | 0.7549 | 0.5806 | 0.080* | |
C31 | 0.0331 (5) | 0.3548 (2) | 0.67134 (16) | 0.0357 (8) | |
C32 | 0.1964 (5) | 0.3120 (3) | 0.69802 (18) | 0.0444 (9) | |
Br32 | 0.23614 (7) | 0.16981 (3) | 0.68887 (3) | 0.0746 (2) | |
C33 | 0.3352 (6) | 0.3685 (4) | 0.7308 (2) | 0.0629 (13) | |
H33 | 0.4435 | 0.3377 | 0.7491 | 0.076* | |
C34 | 0.3097 (7) | 0.4713 (4) | 0.7360 (2) | 0.0712 (15) | |
H34 | 0.4033 | 0.5110 | 0.7566 | 0.085* | |
C35 | 0.1467 (8) | 0.5153 (4) | 0.7107 (2) | 0.0685 (14) | |
H35 | 0.1279 | 0.5845 | 0.7158 | 0.082* | |
C36 | 0.0120 (6) | 0.4583 (3) | 0.6783 (2) | 0.0527 (10) | |
H36 | −0.0964 | 0.4895 | 0.6605 | 0.063* | |
C37 | −0.1145 (5) | 0.2952 (3) | 0.6315 (2) | 0.0397 (9) | |
O31 | −0.0853 (3) | 0.29029 (17) | 0.56785 (12) | 0.0409 (6) | |
O32 | −0.2506 (4) | 0.2563 (2) | 0.66127 (13) | 0.0792 (9) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0415 (17) | 0.0396 (15) | 0.0344 (17) | −0.0058 (17) | 0.0099 (16) | −0.0041 (12) |
C2 | 0.048 (2) | 0.044 (2) | 0.035 (2) | 0.0010 (17) | 0.0020 (18) | 0.0005 (17) |
C3 | 0.0376 (18) | 0.0328 (18) | 0.035 (2) | −0.0018 (16) | −0.0022 (16) | −0.0011 (16) |
N4 | 0.0320 (15) | 0.0302 (15) | 0.0348 (18) | −0.0001 (13) | −0.0053 (13) | 0.0004 (13) |
C5 | 0.037 (2) | 0.0373 (19) | 0.033 (2) | −0.0035 (15) | −0.0070 (15) | 0.0017 (15) |
C6 | 0.0376 (19) | 0.045 (2) | 0.051 (2) | −0.0019 (17) | −0.0041 (18) | 0.0004 (19) |
C21 | 0.0355 (18) | 0.0291 (16) | 0.031 (2) | 0.0035 (15) | 0.0023 (16) | −0.0034 (15) |
C22 | 0.0340 (17) | 0.0379 (17) | 0.034 (2) | −0.0008 (18) | −0.0025 (18) | −0.0017 (14) |
C23 | 0.041 (2) | 0.057 (2) | 0.050 (3) | −0.0128 (19) | −0.0041 (18) | 0.001 (2) |
C24 | 0.051 (2) | 0.069 (3) | 0.052 (3) | −0.017 (2) | 0.006 (2) | 0.014 (2) |
C25 | 0.045 (2) | 0.070 (2) | 0.0304 (19) | −0.005 (2) | 0.0032 (18) | 0.0057 (17) |
C26 | 0.039 (2) | 0.045 (2) | 0.034 (2) | −0.0004 (17) | −0.0016 (17) | −0.0041 (17) |
O22 | 0.0488 (14) | 0.0450 (12) | 0.0297 (13) | −0.0095 (13) | −0.0065 (13) | −0.0008 (10) |
C27 | 0.059 (2) | 0.061 (3) | 0.039 (2) | −0.008 (2) | −0.0174 (19) | −0.0053 (19) |
C31 | 0.0362 (19) | 0.046 (2) | 0.025 (2) | −0.0065 (16) | 0.0051 (15) | −0.0024 (15) |
C32 | 0.0384 (19) | 0.065 (2) | 0.030 (2) | −0.0035 (17) | 0.0008 (16) | 0.0064 (19) |
Br32 | 0.0640 (3) | 0.0691 (3) | 0.0907 (4) | 0.0123 (3) | −0.0067 (3) | 0.0203 (3) |
C33 | 0.045 (2) | 0.107 (4) | 0.037 (2) | −0.014 (3) | −0.0080 (19) | 0.012 (2) |
C34 | 0.070 (3) | 0.103 (4) | 0.040 (3) | −0.045 (3) | 0.006 (2) | −0.022 (3) |
C35 | 0.087 (3) | 0.060 (3) | 0.058 (3) | −0.023 (3) | 0.016 (3) | −0.015 (2) |
C36 | 0.058 (2) | 0.051 (2) | 0.049 (3) | −0.004 (2) | 0.002 (2) | −0.006 (2) |
C37 | 0.0325 (19) | 0.048 (2) | 0.039 (2) | 0.0034 (17) | −0.0004 (17) | −0.0047 (18) |
O31 | 0.0475 (14) | 0.0471 (14) | 0.0283 (14) | −0.0077 (12) | 0.0019 (12) | −0.0046 (12) |
O32 | 0.0561 (18) | 0.131 (3) | 0.0509 (17) | −0.044 (2) | 0.0165 (16) | −0.0198 (16) |
N1—C2 | 1.481 (5) | C24—C25 | 1.360 (5) |
N1—C6 | 1.484 (4) | C24—H24 | 0.9300 |
N1—H11 | 0.75 (4) | C25—C26 | 1.386 (5) |
N1—H12 | 0.89 (3) | C25—H25 | 0.9300 |
C2—C3 | 1.506 (5) | C26—H26 | 0.9300 |
C2—H2A | 0.9700 | O22—C27 | 1.417 (4) |
C2—H2B | 0.9700 | C27—H27A | 0.9600 |
C3—N4 | 1.469 (4) | C27—H27B | 0.9600 |
C3—H3A | 0.9700 | C27—H27C | 0.9600 |
C3—H3B | 0.9700 | C31—C32 | 1.375 (5) |
N4—C21 | 1.412 (4) | C31—C36 | 1.383 (4) |
N4—C5 | 1.460 (4) | C31—C37 | 1.512 (5) |
C5—C6 | 1.505 (5) | C32—C33 | 1.381 (5) |
C5—H5A | 0.9700 | C32—Br32 | 1.910 (4) |
C5—H5B | 0.9700 | C33—C34 | 1.375 (7) |
C6—H6A | 0.9700 | C33—H33 | 0.9300 |
C6—H6B | 0.9700 | C34—C35 | 1.370 (7) |
C21—C26 | 1.384 (5) | C34—H34 | 0.9300 |
C21—C22 | 1.419 (4) | C35—C36 | 1.361 (6) |
C22—O22 | 1.366 (4) | C35—H35 | 0.9300 |
C22—C23 | 1.385 (5) | C36—H36 | 0.9300 |
C23—C24 | 1.380 (5) | C37—O32 | 1.226 (4) |
C23—H23 | 0.9300 | C37—O31 | 1.260 (4) |
C2—N1—C6 | 111.8 (3) | C24—C23—H23 | 119.6 |
C2—N1—H11 | 112 (3) | C22—C23—H23 | 119.6 |
C6—N1—H11 | 107 (3) | C25—C24—C23 | 120.5 (4) |
C2—N1—H12 | 109 (2) | C25—C24—H24 | 119.7 |
C6—N1—H12 | 112 (2) | C23—C24—H24 | 119.7 |
H11—N1—H12 | 104 (3) | C24—C25—C26 | 119.3 (3) |
N1—C2—C3 | 109.3 (3) | C24—C25—H25 | 120.3 |
N1—C2—H2A | 109.8 | C26—C25—H25 | 120.3 |
C3—C2—H2A | 109.8 | C21—C26—C25 | 122.3 (3) |
N1—C2—H2B | 109.8 | C21—C26—H26 | 118.8 |
C3—C2—H2B | 109.8 | C25—C26—H26 | 118.8 |
H2A—C2—H2B | 108.3 | C22—O22—C27 | 117.3 (3) |
N4—C3—C2 | 110.1 (3) | O22—C27—H27A | 109.5 |
N4—C3—H3A | 109.6 | O22—C27—H27B | 109.5 |
C2—C3—H3A | 109.6 | H27A—C27—H27B | 109.5 |
N4—C3—H3B | 109.6 | O22—C27—H27C | 109.5 |
C2—C3—H3B | 109.6 | H27A—C27—H27C | 109.5 |
H3A—C3—H3B | 108.2 | H27B—C27—H27C | 109.5 |
C21—N4—C5 | 115.8 (3) | C32—C31—C36 | 117.3 (3) |
C21—N4—C3 | 116.0 (3) | C32—C31—C37 | 123.0 (3) |
C5—N4—C3 | 110.3 (3) | C36—C31—C37 | 119.6 (3) |
N4—C5—C6 | 110.3 (3) | C31—C32—C33 | 122.3 (4) |
N4—C5—H5A | 109.6 | C31—C32—Br32 | 119.4 (3) |
C6—C5—H5A | 109.6 | C33—C32—Br32 | 118.3 (3) |
N4—C5—H5B | 109.6 | C34—C33—C32 | 118.6 (4) |
C6—C5—H5B | 109.6 | C34—C33—H33 | 120.7 |
H5A—C5—H5B | 108.1 | C32—C33—H33 | 120.7 |
N1—C6—C5 | 110.2 (3) | C35—C34—C33 | 120.1 (4) |
N1—C6—H6A | 109.6 | C35—C34—H34 | 119.9 |
C5—C6—H6A | 109.6 | C33—C34—H34 | 119.9 |
N1—C6—H6B | 109.6 | C36—C35—C34 | 120.3 (4) |
C5—C6—H6B | 109.6 | C36—C35—H35 | 119.8 |
H6A—C6—H6B | 108.1 | C34—C35—H35 | 119.8 |
C26—C21—N4 | 123.2 (3) | C35—C36—C31 | 121.4 (4) |
C26—C21—C22 | 117.4 (3) | C35—C36—H36 | 119.3 |
N4—C21—C22 | 119.2 (3) | C31—C36—H36 | 119.3 |
O22—C22—C23 | 124.3 (3) | O32—C37—O31 | 124.8 (3) |
O22—C22—C21 | 116.0 (3) | O32—C37—C31 | 120.3 (3) |
C23—C22—C21 | 119.6 (3) | O31—C37—C31 | 114.9 (3) |
C24—C23—C22 | 120.7 (3) | ||
C6—N1—C2—C3 | −56.0 (4) | N4—C21—C26—C25 | 172.1 (3) |
N1—C2—C3—N4 | 58.1 (4) | C22—C21—C26—C25 | −3.2 (5) |
C2—C3—N4—C21 | 165.1 (3) | C24—C25—C26—C21 | 2.4 (5) |
C2—C3—N4—C5 | −60.7 (3) | C23—C22—O22—C27 | 3.5 (5) |
C21—N4—C5—C6 | −166.1 (3) | C21—C22—O22—C27 | −172.2 (3) |
C3—N4—C5—C6 | 59.7 (4) | C36—C31—C32—C33 | 0.2 (5) |
C2—N1—C6—C5 | 55.3 (4) | C37—C31—C32—C33 | 176.2 (3) |
N4—C5—C6—N1 | −56.5 (4) | C36—C31—C32—Br32 | −179.1 (3) |
C5—N4—C21—C26 | −11.1 (4) | C37—C31—C32—Br32 | −3.1 (4) |
C3—N4—C21—C26 | 120.6 (3) | C31—C32—C33—C34 | −1.0 (6) |
C5—N4—C21—C22 | 164.2 (3) | Br32—C32—C33—C34 | 178.3 (3) |
C3—N4—C21—C22 | −64.2 (4) | C32—C33—C34—C35 | 2.0 (6) |
C26—C21—C22—O22 | 178.3 (3) | C33—C34—C35—C36 | −2.3 (7) |
N4—C21—C22—O22 | 2.8 (4) | C34—C35—C36—C31 | 1.5 (6) |
C26—C21—C22—C23 | 2.4 (5) | C32—C31—C36—C35 | −0.5 (6) |
N4—C21—C22—C23 | −173.2 (3) | C37—C31—C36—C35 | −176.6 (4) |
O22—C22—C23—C24 | −176.4 (4) | C32—C31—C37—O32 | 91.3 (4) |
C21—C22—C23—C24 | −0.8 (5) | C36—C31—C37—O32 | −92.8 (5) |
C22—C23—C24—C25 | 0.0 (6) | C32—C31—C37—O31 | −89.1 (4) |
C23—C24—C25—C26 | −0.7 (6) | C36—C31—C37—O31 | 86.8 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H11···O31 | 0.75 (4) | 1.98 (4) | 2.726 (4) | 170 (4) |
N1—H12···O31i | 0.88 (3) | 1.86 (3) | 2.712 (4) | 163 (3) |
C25—H25···O32ii | 0.93 | 2.56 | 3.488 (4) | 173 |
C26—H26···Cg1ii | 0.93 | 2.93 | 3.697 (4) | 141 |
Symmetry codes: (i) x+1/2, −y+1/2, −z+1; (ii) −x+1/2, −y+1, z−1/2. |
C11H17N2O+·C7H4IO2− | Dx = 1.595 Mg m−3 |
Mr = 440.27 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 3735 reflections |
a = 7.0101 (4) Å | θ = 2.6–27.8° |
b = 13.3796 (6) Å | µ = 1.76 mm−1 |
c = 19.5524 (6) Å | T = 293 K |
V = 1833.87 (14) Å3 | Block, orange |
Z = 4 | 0.50 × 0.50 × 0.48 mm |
F(000) = 880 |
Oxford Diffraction Xcalibur with Sapphire CCD diffractometer | 3735 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 3036 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.019 |
ω scans | θmax = 27.8°, θmin = 2.6° |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | h = −5→9 |
Tmin = 0.373, Tmax = 0.431 | k = −17→16 |
7500 measured reflections | l = −25→25 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.032 | w = 1/[σ2(Fo2) + (0.0306P)2 + 0.7308P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.071 | (Δ/σ)max < 0.001 |
S = 1.05 | Δρmax = 0.46 e Å−3 |
3735 reflections | Δρmin = −0.65 e Å−3 |
237 parameters | Absolute structure: Flack x determined using 1045 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
17 restraints | Absolute structure parameter: 0.004 (10) |
Primary atom site location: difference Fourier map |
Experimental. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. |
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) | |
N1 | 0.7532 (6) | 0.6404 (2) | 0.49690 (15) | 0.0402 (7) | |
H11 | 0.8436 | 0.6650 | 0.4697 | 0.048* | |
H12 | 0.7154 | 0.6890 | 0.5249 | 0.048* | |
C2 | 0.5901 (6) | 0.6069 (4) | 0.4550 (2) | 0.0423 (11) | |
H2A | 0.6330 | 0.5584 | 0.4215 | 0.051* | |
H2B | 0.5361 | 0.6634 | 0.4307 | 0.051* | |
C3 | 0.4399 (6) | 0.5604 (3) | 0.5005 (2) | 0.0387 (10) | |
H3A | 0.3923 | 0.6100 | 0.5324 | 0.046* | |
H3B | 0.3338 | 0.5374 | 0.4728 | 0.046* | |
N4 | 0.5212 (5) | 0.4761 (3) | 0.53831 (17) | 0.0339 (8) | |
C5 | 0.6810 (6) | 0.5097 (3) | 0.5809 (2) | 0.0396 (10) | |
H5A | 0.7349 | 0.4530 | 0.6051 | 0.048* | |
H5B | 0.6356 | 0.5574 | 0.6145 | 0.048* | |
C6 | 0.8318 (7) | 0.5575 (4) | 0.5374 (3) | 0.0487 (12) | |
H6A | 0.9335 | 0.5823 | 0.5664 | 0.058* | |
H6B | 0.8857 | 0.5078 | 0.5068 | 0.058* | |
C21 | 0.3893 (5) | 0.4115 (3) | 0.5700 (2) | 0.0338 (9) | |
C22 | 0.2609 (8) | 0.3565 (3) | 0.52887 (19) | 0.0372 (9) | |
C23 | 0.1420 (7) | 0.2860 (4) | 0.5579 (3) | 0.0517 (12) | |
H23 | 0.0584 | 0.2496 | 0.5307 | 0.062* | |
C24 | 0.1478 (8) | 0.2697 (4) | 0.6279 (3) | 0.0583 (14) | |
H24 | 0.0678 | 0.2219 | 0.6472 | 0.070* | |
C25 | 0.2675 (8) | 0.3219 (4) | 0.6684 (2) | 0.0527 (12) | |
H25 | 0.2700 | 0.3102 | 0.7153 | 0.063* | |
C26 | 0.3866 (6) | 0.3931 (3) | 0.6399 (2) | 0.0418 (11) | |
H26 | 0.4670 | 0.4296 | 0.6683 | 0.050* | |
O22 | 0.2722 (6) | 0.3732 (2) | 0.45961 (14) | 0.0432 (7) | |
C27 | 0.1621 (8) | 0.3095 (4) | 0.4164 (3) | 0.0574 (14) | |
H27A | 0.0289 | 0.3190 | 0.4257 | 0.086* | |
H27B | 0.1959 | 0.2411 | 0.4249 | 0.086* | |
H27C | 0.1874 | 0.3255 | 0.3694 | 0.086* | |
C31 | 0.9641 (6) | 0.6382 (4) | 0.3324 (2) | 0.0387 (10) | |
C32 | 0.8007 (6) | 0.6775 (4) | 0.3027 (2) | 0.0421 (11) | |
I32 | 0.74794 (6) | 0.83201 (2) | 0.30799 (2) | 0.06407 (13) | |
C33 | 0.6680 (8) | 0.6168 (5) | 0.2703 (3) | 0.0596 (15) | |
H33 | 0.5591 | 0.6443 | 0.2506 | 0.072* | |
C34 | 0.7001 (8) | 0.5157 (5) | 0.2677 (3) | 0.0689 (19) | |
H34 | 0.6110 | 0.4741 | 0.2470 | 0.083* | |
C35 | 0.8613 (10) | 0.4758 (5) | 0.2953 (3) | 0.0660 (16) | |
H35 | 0.8834 | 0.4075 | 0.2922 | 0.079* | |
C36 | 0.9913 (7) | 0.5360 (4) | 0.3277 (3) | 0.0536 (13) | |
H36 | 1.0999 | 0.5075 | 0.3469 | 0.064* | |
C37 | 1.1071 (6) | 0.7004 (3) | 0.3715 (2) | 0.0389 (10) | 0.54 (9) |
O31 | 1.072 (4) | 0.699 (3) | 0.4352 (5) | 0.033 (3) | 0.54 (9) |
O32 | 1.233 (4) | 0.750 (3) | 0.3440 (12) | 0.065 (5) | 0.54 (9) |
C38 | 1.1071 (6) | 0.7004 (3) | 0.3715 (2) | 0.0389 (10) | 0.46 (9) |
O33 | 1.070 (4) | 0.726 (3) | 0.4325 (7) | 0.030 (4) | 0.46 (9) |
O34 | 1.258 (3) | 0.716 (4) | 0.3417 (13) | 0.065 (6) | 0.46 (9) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0418 (17) | 0.0403 (16) | 0.0384 (16) | −0.005 (3) | 0.013 (2) | −0.0056 (13) |
C2 | 0.045 (3) | 0.047 (3) | 0.035 (2) | −0.002 (2) | 0.002 (2) | −0.002 (2) |
C3 | 0.042 (2) | 0.036 (2) | 0.038 (2) | −0.003 (2) | −0.005 (2) | 0.001 (2) |
N4 | 0.0337 (19) | 0.0347 (19) | 0.0334 (18) | −0.0026 (16) | −0.0045 (15) | −0.0008 (16) |
C5 | 0.037 (2) | 0.044 (2) | 0.038 (2) | −0.0003 (19) | −0.0061 (19) | −0.004 (2) |
C6 | 0.040 (2) | 0.053 (3) | 0.054 (3) | −0.001 (2) | −0.005 (2) | −0.006 (3) |
C21 | 0.031 (2) | 0.034 (2) | 0.036 (2) | 0.0025 (18) | 0.0003 (19) | −0.0023 (19) |
C22 | 0.037 (2) | 0.038 (2) | 0.0362 (19) | 0.002 (3) | 0.000 (3) | 0.0002 (15) |
C23 | 0.044 (3) | 0.057 (3) | 0.054 (3) | −0.010 (2) | −0.004 (2) | 0.004 (3) |
C24 | 0.052 (3) | 0.068 (4) | 0.055 (3) | −0.016 (3) | 0.008 (3) | 0.017 (3) |
C25 | 0.050 (3) | 0.068 (3) | 0.041 (2) | −0.003 (4) | 0.006 (3) | 0.010 (2) |
C26 | 0.042 (2) | 0.050 (3) | 0.033 (2) | 0.000 (2) | 0.002 (2) | −0.004 (2) |
O22 | 0.0477 (19) | 0.0469 (15) | 0.0350 (13) | −0.0054 (18) | −0.0046 (17) | 0.0000 (12) |
C27 | 0.063 (3) | 0.067 (3) | 0.043 (3) | −0.015 (3) | −0.014 (3) | −0.007 (3) |
C31 | 0.035 (2) | 0.051 (3) | 0.030 (2) | −0.003 (2) | 0.0036 (18) | −0.004 (2) |
C32 | 0.041 (3) | 0.055 (3) | 0.030 (2) | −0.0081 (19) | 0.0015 (18) | 0.004 (2) |
I32 | 0.05832 (19) | 0.0631 (2) | 0.0708 (2) | 0.0097 (3) | −0.0032 (3) | 0.01731 (17) |
C33 | 0.049 (3) | 0.090 (4) | 0.041 (3) | −0.014 (3) | −0.010 (2) | 0.003 (3) |
C34 | 0.073 (5) | 0.087 (5) | 0.047 (3) | −0.037 (3) | 0.004 (3) | −0.017 (3) |
C35 | 0.078 (4) | 0.058 (3) | 0.062 (4) | −0.014 (3) | 0.016 (3) | −0.020 (3) |
C36 | 0.050 (3) | 0.054 (3) | 0.056 (3) | −0.001 (2) | 0.001 (2) | −0.009 (3) |
C37 | 0.032 (2) | 0.046 (3) | 0.039 (3) | −0.002 (2) | 0.000 (2) | −0.003 (2) |
O31 | 0.051 (5) | 0.015 (9) | 0.034 (4) | −0.012 (7) | 0.003 (4) | −0.005 (3) |
O32 | 0.066 (8) | 0.072 (11) | 0.057 (6) | −0.031 (7) | 0.019 (7) | −0.022 (6) |
C38 | 0.032 (2) | 0.046 (3) | 0.039 (3) | −0.002 (2) | 0.000 (2) | −0.003 (2) |
O33 | 0.042 (5) | 0.010 (9) | 0.038 (5) | −0.009 (7) | 0.002 (4) | −0.004 (4) |
O34 | 0.039 (6) | 0.105 (16) | 0.053 (6) | −0.020 (9) | 0.009 (6) | −0.037 (9) |
N1—C6 | 1.470 (6) | C24—C25 | 1.350 (7) |
N1—C2 | 1.476 (6) | C24—H24 | 0.9300 |
N1—H11 | 0.8900 | C25—C26 | 1.383 (6) |
N1—H12 | 0.8900 | C25—H25 | 0.9300 |
C2—C3 | 1.512 (6) | C26—H26 | 0.9300 |
C2—H2A | 0.9700 | O22—C27 | 1.428 (6) |
C2—H2B | 0.9700 | C27—H27A | 0.9600 |
C3—N4 | 1.464 (5) | C27—H27B | 0.9600 |
C3—H3A | 0.9700 | C27—H27C | 0.9600 |
C3—H3B | 0.9700 | C31—C36 | 1.384 (7) |
N4—C21 | 1.410 (5) | C31—C32 | 1.387 (6) |
N4—C5 | 1.466 (6) | C31—C37 | 1.511 (6) |
C5—C6 | 1.500 (7) | C32—C33 | 1.388 (7) |
C5—H5A | 0.9700 | C32—I32 | 2.103 (5) |
C5—H5B | 0.9700 | C33—C34 | 1.372 (9) |
C6—H6A | 0.9700 | C33—H33 | 0.9300 |
C6—H6B | 0.9700 | C34—C35 | 1.361 (8) |
C21—C26 | 1.389 (6) | C34—H34 | 0.9300 |
C21—C22 | 1.413 (6) | C35—C36 | 1.370 (8) |
C22—O22 | 1.375 (5) | C35—H35 | 0.9300 |
C22—C23 | 1.382 (6) | C36—H36 | 0.9300 |
C23—C24 | 1.385 (7) | C37—O32 | 1.226 (9) |
C23—H23 | 0.9300 | C37—O31 | 1.269 (8) |
C6—N1—C2 | 111.1 (3) | C22—C23—H23 | 120.1 |
C6—N1—H11 | 109.4 | C24—C23—H23 | 120.1 |
C2—N1—H11 | 109.4 | C25—C24—C23 | 121.1 (5) |
C6—N1—H12 | 109.4 | C25—C24—H24 | 119.5 |
C2—N1—H12 | 109.4 | C23—C24—H24 | 119.5 |
H11—N1—H12 | 108.0 | C24—C25—C26 | 119.7 (4) |
N1—C2—C3 | 109.8 (3) | C24—C25—H25 | 120.2 |
N1—C2—H2A | 109.7 | C26—C25—H25 | 120.2 |
C3—C2—H2A | 109.7 | C25—C26—C21 | 121.8 (4) |
N1—C2—H2B | 109.7 | C25—C26—H26 | 119.1 |
C3—C2—H2B | 109.7 | C21—C26—H26 | 119.1 |
H2A—C2—H2B | 108.2 | C22—O22—C27 | 117.1 (4) |
N4—C3—C2 | 110.1 (4) | O22—C27—H27A | 109.5 |
N4—C3—H3A | 109.6 | O22—C27—H27B | 109.5 |
C2—C3—H3A | 109.6 | H27A—C27—H27B | 109.5 |
N4—C3—H3B | 109.6 | O22—C27—H27C | 109.5 |
C2—C3—H3B | 109.6 | H27A—C27—H27C | 109.5 |
H3A—C3—H3B | 108.2 | H27B—C27—H27C | 109.5 |
C21—N4—C3 | 116.0 (3) | C36—C31—C32 | 117.4 (4) |
C21—N4—C5 | 116.1 (3) | C36—C31—C37 | 119.1 (4) |
C3—N4—C5 | 110.4 (3) | C32—C31—C37 | 123.4 (4) |
N4—C5—C6 | 110.3 (4) | C31—C32—C33 | 121.5 (5) |
N4—C5—H5A | 109.6 | C31—C32—I32 | 119.8 (3) |
C6—C5—H5A | 109.6 | C33—C32—I32 | 118.6 (4) |
N4—C5—H5B | 109.6 | C34—C33—C32 | 118.9 (5) |
C6—C5—H5B | 109.6 | C34—C33—H33 | 120.6 |
H5A—C5—H5B | 108.1 | C32—C33—H33 | 120.6 |
N1—C6—C5 | 111.3 (4) | C35—C34—C33 | 120.6 (5) |
N1—C6—H6A | 109.4 | C35—C34—H34 | 119.7 |
C5—C6—H6A | 109.4 | C33—C34—H34 | 119.7 |
N1—C6—H6B | 109.4 | C34—C35—C36 | 120.3 (6) |
C5—C6—H6B | 109.4 | C34—C35—H35 | 119.8 |
H6A—C6—H6B | 108.0 | C36—C35—H35 | 119.8 |
C26—C21—N4 | 123.4 (4) | C35—C36—C31 | 121.3 (5) |
C26—C21—C22 | 117.3 (4) | C35—C36—H36 | 119.4 |
N4—C21—C22 | 119.1 (4) | C31—C36—H36 | 119.4 |
O22—C22—C23 | 123.4 (4) | O32—C37—O31 | 125.5 (12) |
O22—C22—C21 | 116.0 (4) | O32—C37—C31 | 123.5 (13) |
C23—C22—C21 | 120.4 (4) | O31—C37—C31 | 111.0 (13) |
C22—C23—C24 | 119.7 (5) | ||
C6—N1—C2—C3 | 56.3 (5) | C24—C25—C26—C21 | −1.1 (8) |
N1—C2—C3—N4 | −58.4 (5) | N4—C21—C26—C25 | −173.6 (4) |
C2—C3—N4—C21 | −165.5 (4) | C22—C21—C26—C25 | 1.8 (7) |
C2—C3—N4—C5 | 59.7 (5) | C23—C22—O22—C27 | −3.7 (7) |
C21—N4—C5—C6 | 167.0 (4) | C21—C22—O22—C27 | 172.1 (4) |
C3—N4—C5—C6 | −58.3 (5) | C36—C31—C32—C33 | 0.8 (6) |
C2—N1—C6—C5 | −55.6 (5) | C37—C31—C32—C33 | −176.6 (4) |
N4—C5—C6—N1 | 56.2 (5) | C36—C31—C32—I32 | 179.7 (3) |
C3—N4—C21—C26 | −121.0 (4) | C37—C31—C32—I32 | 2.3 (5) |
C5—N4—C21—C26 | 11.1 (6) | C31—C32—C33—C34 | 0.0 (7) |
C3—N4—C21—C22 | 63.7 (5) | I32—C32—C33—C34 | −178.9 (4) |
C5—N4—C21—C22 | −164.2 (4) | C32—C33—C34—C35 | −1.4 (8) |
C26—C21—C22—O22 | −177.4 (4) | C33—C34—C35—C36 | 1.8 (8) |
N4—C21—C22—O22 | −1.8 (6) | C34—C35—C36—C31 | −0.9 (8) |
C26—C21—C22—C23 | −1.5 (6) | C32—C31—C36—C35 | −0.4 (7) |
N4—C21—C22—C23 | 174.1 (4) | C37—C31—C36—C35 | 177.1 (5) |
O22—C22—C23—C24 | 176.1 (5) | C36—C31—C37—O32 | 101 (2) |
C21—C22—C23—C24 | 0.5 (8) | C32—C31—C37—O32 | −82 (2) |
C22—C23—C24—C25 | 0.2 (9) | C36—C31—C37—O31 | −82.8 (18) |
C23—C24—C25—C26 | 0.1 (9) | C32—C31—C37—O31 | 94.6 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H11···O31 | 0.89 | 1.80 | 2.66 (3) | 162 |
N1—H11···O33 | 0.89 | 1.93 | 2.80 (3) | 165 |
N1—H12···O31i | 0.89 | 1.97 | 2.83 (3) | 162 |
N1—H12···O33i | 0.89 | 1.74 | 2.60 (3) | 161 |
C25—H25···O34ii | 0.93 | 2.50 | 3.43 (3) | 174 |
C26—H26···Cg1ii | 0.93 | 2.93 | 3.716 (5) | 143 |
Symmetry codes: (i) x−1/2, −y+3/2, −z+1; (ii) −x+3/2, −y+1, z+1/2. |
C11H17N2O+·C8H7O2− | Z = 2 |
Mr = 328.40 | F(000) = 352 |
Triclinic, P1 | Dx = 1.206 Mg m−3 |
a = 7.826 (1) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.320 (2) Å | Cell parameters from 3838 reflections |
c = 12.055 (3) Å | θ = 2.7–27.7° |
α = 78.37 (2)° | µ = 0.08 mm−1 |
β = 78.27 (2)° | T = 296 K |
γ = 73.83 (2)° | Block, colourless |
V = 904.6 (3) Å3 | 0.48 × 0.48 × 0.40 mm |
Oxford Diffraction Xcalibur with Sapphire CCD diffractometer | 3838 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 2600 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.013 |
ω scans | θmax = 27.7°, θmin = 2.7° |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | h = −5→10 |
Tmin = 0.883, Tmax = 0.968 | k = −11→13 |
6091 measured reflections | l = −15→15 |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.042 | w = 1/[σ2(Fo2) + (0.0611P)2 + 0.0332P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.119 | (Δ/σ)max < 0.001 |
S = 1.06 | Δρmax = 0.16 e Å−3 |
3838 reflections | Δρmin = −0.16 e Å−3 |
226 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.057 (5) |
Primary atom site location: difference Fourier map |
Experimental. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. |
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 | ||
N1 | 0.42898 (16) | 0.55387 (12) | 0.64034 (10) | 0.0429 (3) | |
H11 | 0.3320 (19) | 0.5684 (15) | 0.5920 (12) | 0.051* | |
H12 | 0.5095 (19) | 0.4646 (16) | 0.6376 (12) | 0.051* | |
C2 | 0.33370 (18) | 0.55987 (15) | 0.75988 (11) | 0.0449 (3) | |
H2A | 0.2790 | 0.4832 | 0.7859 | 0.054* | |
H2B | 0.2384 | 0.6433 | 0.7619 | 0.054* | |
C3 | 0.46231 (18) | 0.55582 (14) | 0.83911 (11) | 0.0448 (3) | |
H3A | 0.3967 | 0.5651 | 0.9157 | 0.054* | |
H3B | 0.5512 | 0.4688 | 0.8430 | 0.054* | |
N4 | 0.55258 (15) | 0.66676 (12) | 0.79702 (9) | 0.0445 (3) | |
C5 | 0.6584 (2) | 0.64945 (17) | 0.68405 (12) | 0.0534 (4) | |
H5A | 0.7448 | 0.5613 | 0.6881 | 0.064* | |
H5B | 0.7241 | 0.7198 | 0.6581 | 0.064* | |
C6 | 0.5332 (2) | 0.65903 (17) | 0.60108 (12) | 0.0542 (4) | |
H6A | 0.4510 | 0.7490 | 0.5945 | 0.065* | |
H6B | 0.6027 | 0.6466 | 0.5259 | 0.065* | |
C21 | 0.63967 (18) | 0.69298 (14) | 0.87963 (11) | 0.0434 (3) | |
C22 | 0.53136 (18) | 0.75748 (14) | 0.97177 (12) | 0.0453 (3) | |
C23 | 0.6112 (2) | 0.78557 (16) | 1.05340 (13) | 0.0562 (4) | |
H23 | 0.5396 | 0.8262 | 1.1149 | 0.067* | |
C24 | 0.7965 (2) | 0.75375 (18) | 1.04446 (14) | 0.0628 (4) | |
H24 | 0.8488 | 0.7740 | 1.0995 | 0.075* | |
C25 | 0.9036 (2) | 0.6926 (2) | 0.95519 (15) | 0.0693 (5) | |
H25 | 1.0283 | 0.6715 | 0.9492 | 0.083* | |
C26 | 0.8242 (2) | 0.66219 (18) | 0.87324 (14) | 0.0599 (4) | |
H26 | 0.8973 | 0.6202 | 0.8129 | 0.072* | |
O22 | 0.34998 (13) | 0.78566 (11) | 0.97381 (9) | 0.0602 (3) | |
C27 | 0.2347 (2) | 0.85827 (19) | 1.06138 (16) | 0.0734 (5) | |
H27A | 0.1119 | 0.8784 | 1.0492 | 0.110* | |
H27B | 0.2676 | 0.9419 | 1.0587 | 0.110* | |
H27C | 0.2472 | 0.8032 | 1.1350 | 0.110* | |
C31 | 0.02692 (17) | 0.80006 (14) | 0.37927 (11) | 0.0434 (3) | |
C32 | 0.0231 (2) | 0.93671 (15) | 0.33658 (14) | 0.0571 (4) | |
C33 | −0.1295 (3) | 1.01830 (17) | 0.29036 (17) | 0.0752 (5) | |
H33 | −0.1323 | 1.1089 | 0.2594 | 0.090* | |
C34 | −0.2735 (2) | 0.9696 (2) | 0.28923 (16) | 0.0774 (6) | |
H34 | −0.3733 | 1.0266 | 0.2588 | 0.093* | |
C35 | −0.2708 (2) | 0.8359 (2) | 0.33318 (14) | 0.0660 (5) | |
H35 | −0.3690 | 0.8019 | 0.3331 | 0.079* | |
C36 | −0.12087 (18) | 0.75165 (16) | 0.37783 (12) | 0.0523 (4) | |
H36 | −0.1195 | 0.6609 | 0.4074 | 0.063* | |
C37 | 0.18760 (19) | 0.70027 (14) | 0.42484 (13) | 0.0482 (4) | |
O31 | 0.15924 (14) | 0.62406 (13) | 0.51830 (10) | 0.0692 (3) | |
O32 | 0.34037 (13) | 0.69583 (10) | 0.36497 (10) | 0.0615 (3) | |
C38 | 0.1751 (3) | 0.99828 (18) | 0.3413 (2) | 0.0863 (6) | |
H38A | 0.1307 | 1.0954 | 0.3377 | 0.130* | |
H38B | 0.2688 | 0.9785 | 0.2775 | 0.130* | |
H38C | 0.2222 | 0.9600 | 0.4116 | 0.130* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0422 (6) | 0.0442 (7) | 0.0423 (7) | −0.0085 (5) | −0.0076 (5) | −0.0088 (5) |
C2 | 0.0437 (7) | 0.0458 (8) | 0.0438 (8) | −0.0139 (6) | −0.0032 (6) | −0.0033 (6) |
C3 | 0.0488 (8) | 0.0453 (8) | 0.0400 (7) | −0.0170 (6) | −0.0048 (6) | −0.0008 (6) |
N4 | 0.0510 (7) | 0.0487 (7) | 0.0364 (6) | −0.0207 (5) | −0.0022 (5) | −0.0057 (5) |
C5 | 0.0586 (9) | 0.0655 (10) | 0.0425 (8) | −0.0319 (8) | 0.0027 (7) | −0.0102 (7) |
C6 | 0.0678 (10) | 0.0605 (9) | 0.0385 (8) | −0.0287 (8) | −0.0011 (7) | −0.0065 (7) |
C21 | 0.0503 (8) | 0.0426 (7) | 0.0391 (7) | −0.0187 (6) | −0.0051 (6) | −0.0021 (6) |
C22 | 0.0480 (8) | 0.0441 (8) | 0.0441 (8) | −0.0156 (6) | −0.0054 (6) | −0.0032 (6) |
C23 | 0.0658 (10) | 0.0620 (10) | 0.0452 (9) | −0.0237 (8) | −0.0026 (7) | −0.0134 (7) |
C24 | 0.0649 (10) | 0.0836 (12) | 0.0523 (9) | −0.0336 (9) | −0.0114 (8) | −0.0148 (9) |
C25 | 0.0497 (9) | 0.0982 (13) | 0.0662 (11) | −0.0248 (9) | −0.0088 (8) | −0.0183 (10) |
C26 | 0.0517 (9) | 0.0763 (11) | 0.0549 (10) | −0.0196 (8) | −0.0007 (7) | −0.0200 (8) |
O22 | 0.0496 (6) | 0.0720 (7) | 0.0595 (7) | −0.0088 (5) | −0.0046 (5) | −0.0237 (6) |
C27 | 0.0582 (10) | 0.0747 (12) | 0.0849 (13) | −0.0085 (9) | 0.0044 (9) | −0.0336 (10) |
C31 | 0.0417 (7) | 0.0445 (8) | 0.0389 (7) | −0.0049 (6) | −0.0018 (6) | −0.0075 (6) |
C32 | 0.0583 (9) | 0.0425 (8) | 0.0643 (10) | −0.0064 (7) | 0.0005 (8) | −0.0127 (7) |
C33 | 0.0775 (12) | 0.0437 (9) | 0.0853 (13) | 0.0025 (8) | −0.0062 (10) | 0.0020 (9) |
C34 | 0.0550 (10) | 0.0801 (13) | 0.0749 (12) | 0.0088 (9) | −0.0136 (9) | 0.0064 (10) |
C35 | 0.0473 (9) | 0.0850 (13) | 0.0590 (10) | −0.0117 (8) | −0.0116 (7) | 0.0010 (9) |
C36 | 0.0460 (8) | 0.0585 (9) | 0.0491 (9) | −0.0137 (7) | −0.0082 (6) | 0.0011 (7) |
C37 | 0.0462 (8) | 0.0445 (8) | 0.0573 (9) | −0.0121 (6) | −0.0131 (7) | −0.0091 (7) |
O31 | 0.0594 (7) | 0.0788 (8) | 0.0667 (8) | −0.0227 (6) | −0.0250 (6) | 0.0177 (6) |
O32 | 0.0422 (6) | 0.0544 (7) | 0.0800 (8) | −0.0033 (5) | −0.0046 (5) | −0.0094 (6) |
C38 | 0.0885 (13) | 0.0510 (10) | 0.1240 (18) | −0.0242 (10) | −0.0133 (12) | −0.0174 (11) |
N1—C6 | 1.4820 (18) | C25—C26 | 1.394 (2) |
N1—C2 | 1.4866 (18) | C25—H25 | 0.9300 |
N1—H11 | 1.010 (15) | C26—H26 | 0.9300 |
N1—H12 | 0.963 (16) | O22—C27 | 1.4300 (19) |
C2—C3 | 1.5094 (19) | C27—H27A | 0.9600 |
C2—H2A | 0.9700 | C27—H27B | 0.9600 |
C2—H2B | 0.9700 | C27—H27C | 0.9600 |
C3—N4 | 1.4621 (17) | C31—C36 | 1.3861 (19) |
C3—H3A | 0.9700 | C31—C32 | 1.395 (2) |
C3—H3B | 0.9700 | C31—C37 | 1.508 (2) |
N4—C21 | 1.4202 (18) | C32—C33 | 1.402 (2) |
N4—C5 | 1.4592 (18) | C32—C38 | 1.511 (2) |
C5—C6 | 1.508 (2) | C33—C34 | 1.359 (3) |
C5—H5A | 0.9700 | C33—H33 | 0.9300 |
C5—H5B | 0.9700 | C34—C35 | 1.370 (3) |
C6—H6A | 0.9700 | C34—H34 | 0.9300 |
C6—H6B | 0.9700 | C35—C36 | 1.387 (2) |
C21—C26 | 1.379 (2) | C35—H35 | 0.9300 |
C21—C22 | 1.413 (2) | C36—H36 | 0.9300 |
C22—O22 | 1.3634 (16) | C37—O31 | 1.2552 (17) |
C22—C23 | 1.381 (2) | C37—O32 | 1.2587 (16) |
C23—C24 | 1.382 (2) | C38—H38A | 0.9600 |
C23—H23 | 0.9300 | C38—H38B | 0.9600 |
C24—C25 | 1.368 (2) | C38—H38C | 0.9600 |
C24—H24 | 0.9300 | ||
C6—N1—C2 | 111.69 (11) | C25—C24—H24 | 119.8 |
C6—N1—H11 | 111.2 (8) | C23—C24—H24 | 119.8 |
C2—N1—H11 | 105.7 (8) | C24—C25—C26 | 119.46 (15) |
C6—N1—H12 | 109.4 (8) | C24—C25—H25 | 120.3 |
C2—N1—H12 | 108.3 (9) | C26—C25—H25 | 120.3 |
H11—N1—H12 | 110.4 (12) | C21—C26—C25 | 121.52 (15) |
N1—C2—C3 | 110.86 (11) | C21—C26—H26 | 119.2 |
N1—C2—H2A | 109.5 | C25—C26—H26 | 119.2 |
C3—C2—H2A | 109.5 | C22—O22—C27 | 117.89 (12) |
N1—C2—H2B | 109.5 | O22—C27—H27A | 109.5 |
C3—C2—H2B | 109.5 | O22—C27—H27B | 109.5 |
H2A—C2—H2B | 108.1 | H27A—C27—H27B | 109.5 |
N4—C3—C2 | 109.85 (11) | O22—C27—H27C | 109.5 |
N4—C3—H3A | 109.7 | H27A—C27—H27C | 109.5 |
C2—C3—H3A | 109.7 | H27B—C27—H27C | 109.5 |
N4—C3—H3B | 109.7 | C36—C31—C32 | 119.20 (14) |
C2—C3—H3B | 109.7 | C36—C31—C37 | 117.89 (13) |
H3A—C3—H3B | 108.2 | C32—C31—C37 | 122.89 (13) |
C21—N4—C5 | 117.07 (11) | C31—C32—C33 | 117.94 (15) |
C21—N4—C3 | 113.60 (10) | C31—C32—C38 | 122.05 (15) |
C5—N4—C3 | 109.82 (11) | C33—C32—C38 | 119.99 (16) |
N4—C5—C6 | 109.00 (12) | C34—C33—C32 | 122.27 (17) |
N4—C5—H5A | 109.9 | C34—C33—H33 | 118.9 |
C6—C5—H5A | 109.9 | C32—C33—H33 | 118.9 |
N4—C5—H5B | 109.9 | C33—C34—C35 | 119.66 (17) |
C6—C5—H5B | 109.9 | C33—C34—H34 | 120.2 |
H5A—C5—H5B | 108.3 | C35—C34—H34 | 120.2 |
N1—C6—C5 | 110.75 (12) | C34—C35—C36 | 119.66 (17) |
N1—C6—H6A | 109.5 | C34—C35—H35 | 120.2 |
C5—C6—H6A | 109.5 | C36—C35—H35 | 120.2 |
N1—C6—H6B | 109.5 | C31—C36—C35 | 121.23 (15) |
C5—C6—H6B | 109.5 | C31—C36—H36 | 119.4 |
H6A—C6—H6B | 108.1 | C35—C36—H36 | 119.4 |
C26—C21—C22 | 118.20 (13) | O31—C37—O32 | 124.33 (14) |
C26—C21—N4 | 123.60 (13) | O31—C37—C31 | 117.71 (13) |
C22—C21—N4 | 118.18 (12) | O32—C37—C31 | 117.92 (13) |
O22—C22—C23 | 124.39 (13) | C32—C38—H38A | 109.5 |
O22—C22—C21 | 115.73 (13) | C32—C38—H38B | 109.5 |
C23—C22—C21 | 119.88 (13) | H38A—C38—H38B | 109.5 |
C22—C23—C24 | 120.54 (15) | C32—C38—H38C | 109.5 |
C22—C23—H23 | 119.7 | H38A—C38—H38C | 109.5 |
C24—C23—H23 | 119.7 | H38B—C38—H38C | 109.5 |
C25—C24—C23 | 120.39 (15) | ||
C6—N1—C2—C3 | −52.32 (16) | C22—C21—C26—C25 | 0.3 (2) |
N1—C2—C3—N4 | 56.11 (15) | N4—C21—C26—C25 | 178.59 (14) |
C2—C3—N4—C21 | 164.70 (11) | C24—C25—C26—C21 | 0.3 (3) |
C2—C3—N4—C5 | −62.04 (15) | C23—C22—O22—C27 | 4.9 (2) |
C21—N4—C5—C6 | −165.56 (12) | C21—C22—O22—C27 | −176.31 (13) |
C3—N4—C5—C6 | 62.98 (16) | C36—C31—C32—C33 | −2.0 (2) |
C2—N1—C6—C5 | 53.64 (16) | C37—C31—C32—C33 | 176.40 (15) |
N4—C5—C6—N1 | −58.51 (17) | C36—C31—C32—C38 | 176.65 (15) |
C5—N4—C21—C26 | −20.7 (2) | C37—C31—C32—C38 | −4.9 (2) |
C3—N4—C21—C26 | 109.01 (15) | C31—C32—C33—C34 | 2.0 (3) |
C5—N4—C21—C22 | 157.56 (13) | C38—C32—C33—C34 | −176.74 (18) |
C3—N4—C21—C22 | −72.74 (15) | C32—C33—C34—C35 | −0.8 (3) |
C26—C21—C22—O22 | 179.95 (13) | C33—C34—C35—C36 | −0.3 (3) |
N4—C21—C22—O22 | 1.60 (18) | C32—C31—C36—C35 | 1.0 (2) |
C26—C21—C22—C23 | −1.2 (2) | C37—C31—C36—C35 | −177.50 (14) |
N4—C21—C22—C23 | −179.54 (12) | C34—C35—C36—C31 | 0.2 (2) |
O22—C22—C23—C24 | −179.86 (14) | C36—C31—C37—O31 | −47.61 (19) |
C21—C22—C23—C24 | 1.4 (2) | C32—C31—C37—O31 | 133.92 (15) |
C22—C23—C24—C25 | −0.7 (2) | C36—C31—C37—O32 | 130.15 (14) |
C23—C24—C25—C26 | −0.2 (3) | C32—C31—C37—O32 | −48.3 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H11···O31 | 1.010 (15) | 1.673 (15) | 2.6696 (19) | 168.6 (13) |
N1—H12···O32i | 0.963 (16) | 1.745 (16) | 2.7077 (17) | 178.2 (10) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
C11H17N2O+·C7H6NO2− | F(000) = 704 |
Mr = 329.39 | Dx = 1.280 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 14.922 (1) Å | Cell parameters from 3671 reflections |
b = 7.6951 (5) Å | θ = 2.7–27.8° |
c = 15.560 (1) Å | µ = 0.09 mm−1 |
β = 106.911 (8)° | T = 296 K |
V = 1709.4 (2) Å3 | Plate, orange |
Z = 4 | 0.48 × 0.44 × 0.16 mm |
Oxford Diffraction Xcalibur with Sapphire CCD diffractometer | 3668 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 2606 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.014 |
ω scans | θmax = 27.6°, θmin = 2.7° |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | h = −18→15 |
Tmin = 0.830, Tmax = 0.986 | k = −5→9 |
6720 measured reflections | l = −17→20 |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.039 | w = 1/[σ2(Fo2) + (0.0619P)2 + 0.0395P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.112 | (Δ/σ)max < 0.001 |
S = 1.10 | Δρmax = 0.15 e Å−3 |
3668 reflections | Δρmin = −0.24 e Å−3 |
231 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.019 (2) |
Primary atom site location: difference Fourier map |
Experimental. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. |
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 | ||
N1 | 0.60709 (8) | 0.26835 (15) | 0.52995 (8) | 0.0431 (3) | |
H11 | 0.5586 (10) | 0.2606 (17) | 0.4643 (10) | 0.052* | |
H12 | 0.5953 (10) | 0.3661 (19) | 0.5615 (10) | 0.052* | |
C2 | 0.70246 (9) | 0.28650 (18) | 0.51932 (9) | 0.0442 (3) | |
H2A | 0.7056 | 0.3915 | 0.4858 | 0.053* | |
H2B | 0.7155 | 0.1883 | 0.4857 | 0.053* | |
C3 | 0.77450 (9) | 0.29453 (16) | 0.60945 (8) | 0.0385 (3) | |
H3A | 0.8364 | 0.3050 | 0.6015 | 0.046* | |
H3B | 0.7635 | 0.3963 | 0.6417 | 0.046* | |
N4 | 0.77041 (7) | 0.13685 (13) | 0.66227 (7) | 0.0376 (3) | |
C5 | 0.67672 (9) | 0.11904 (18) | 0.67358 (9) | 0.0433 (3) | |
H5A | 0.6642 | 0.2174 | 0.7074 | 0.052* | |
H5B | 0.6741 | 0.0143 | 0.7074 | 0.052* | |
C6 | 0.60307 (9) | 0.11039 (17) | 0.58382 (9) | 0.0458 (3) | |
H6A | 0.6131 | 0.0079 | 0.5515 | 0.055* | |
H6B | 0.5416 | 0.1013 | 0.5928 | 0.055* | |
C21 | 0.84580 (9) | 0.13068 (16) | 0.74309 (9) | 0.0409 (3) | |
C22 | 0.93798 (9) | 0.11685 (17) | 0.73737 (10) | 0.0460 (3) | |
C23 | 1.01328 (10) | 0.1198 (2) | 0.81461 (11) | 0.0600 (4) | |
H23 | 1.0740 | 0.1142 | 0.8102 | 0.072* | |
C24 | 0.99867 (13) | 0.1311 (2) | 0.89743 (11) | 0.0714 (5) | |
H24 | 1.0495 | 0.1345 | 0.9489 | 0.086* | |
C25 | 0.90983 (13) | 0.1373 (3) | 0.90449 (11) | 0.0732 (5) | |
H25 | 0.9001 | 0.1412 | 0.9608 | 0.088* | |
C26 | 0.83373 (11) | 0.1379 (2) | 0.82761 (9) | 0.0559 (4) | |
H26 | 0.7734 | 0.1432 | 0.8332 | 0.067* | |
O22 | 0.94654 (7) | 0.10004 (14) | 0.65293 (7) | 0.0603 (3) | |
C27 | 1.03816 (12) | 0.1063 (3) | 0.64265 (13) | 0.0762 (5) | |
H27A | 1.0342 | 0.0973 | 0.5801 | 0.114* | |
H27B | 1.0747 | 0.0114 | 0.6749 | 0.114* | |
H27C | 1.0675 | 0.2142 | 0.6660 | 0.114* | |
C31 | 0.38418 (8) | 0.30821 (15) | 0.23323 (8) | 0.0341 (3) | |
C32 | 0.30092 (9) | 0.39385 (17) | 0.19135 (9) | 0.0410 (3) | |
H32 | 0.2734 | 0.4636 | 0.2255 | 0.049* | |
C33 | 0.25815 (9) | 0.37762 (17) | 0.10033 (9) | 0.0429 (3) | |
H33 | 0.2021 | 0.4355 | 0.0741 | 0.051* | |
C34 | 0.29810 (9) | 0.27553 (16) | 0.04752 (8) | 0.0373 (3) | |
C35 | 0.38187 (9) | 0.19061 (17) | 0.08919 (8) | 0.0395 (3) | |
H35 | 0.4102 | 0.1226 | 0.0551 | 0.047* | |
C36 | 0.42342 (9) | 0.20608 (16) | 0.18038 (9) | 0.0382 (3) | |
H36 | 0.4789 | 0.1468 | 0.2069 | 0.046* | |
C37 | 0.43113 (9) | 0.32513 (16) | 0.33203 (8) | 0.0379 (3) | |
O31 | 0.50355 (7) | 0.23691 (14) | 0.36411 (6) | 0.0627 (3) | |
O32 | 0.39544 (7) | 0.42404 (13) | 0.37713 (6) | 0.0526 (3) | |
N34 | 0.25457 (10) | 0.25415 (18) | −0.04368 (8) | 0.0501 (3) | |
H341 | 0.2158 (11) | 0.340 (2) | −0.0658 (11) | 0.060* | |
H342 | 0.2928 (11) | 0.211 (2) | −0.0750 (10) | 0.060* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0392 (6) | 0.0463 (7) | 0.0372 (6) | 0.0090 (5) | 0.0006 (5) | −0.0055 (5) |
C2 | 0.0476 (8) | 0.0477 (8) | 0.0356 (7) | 0.0105 (6) | 0.0093 (6) | 0.0029 (6) |
C3 | 0.0364 (7) | 0.0412 (7) | 0.0369 (7) | 0.0019 (5) | 0.0090 (5) | 0.0051 (5) |
N4 | 0.0319 (5) | 0.0418 (6) | 0.0361 (6) | 0.0015 (4) | 0.0054 (4) | 0.0063 (5) |
C5 | 0.0370 (7) | 0.0447 (7) | 0.0471 (8) | −0.0015 (5) | 0.0106 (6) | 0.0064 (6) |
C6 | 0.0352 (7) | 0.0449 (8) | 0.0523 (9) | 0.0009 (5) | 0.0048 (6) | −0.0043 (6) |
C21 | 0.0396 (7) | 0.0402 (7) | 0.0385 (7) | 0.0019 (5) | 0.0045 (6) | 0.0068 (6) |
C22 | 0.0402 (7) | 0.0477 (8) | 0.0459 (8) | 0.0075 (6) | 0.0061 (6) | 0.0066 (6) |
C23 | 0.0402 (8) | 0.0653 (10) | 0.0642 (11) | 0.0072 (7) | −0.0012 (7) | 0.0102 (8) |
C24 | 0.0632 (11) | 0.0846 (13) | 0.0482 (10) | 0.0057 (9) | −0.0124 (8) | 0.0141 (9) |
C25 | 0.0752 (12) | 0.0985 (14) | 0.0378 (9) | 0.0081 (10) | 0.0037 (8) | 0.0151 (9) |
C26 | 0.0529 (9) | 0.0727 (10) | 0.0402 (8) | 0.0057 (7) | 0.0105 (7) | 0.0130 (7) |
O22 | 0.0416 (6) | 0.0838 (8) | 0.0561 (7) | 0.0162 (5) | 0.0150 (5) | 0.0020 (6) |
C27 | 0.0525 (10) | 0.0953 (14) | 0.0880 (14) | 0.0157 (9) | 0.0320 (9) | 0.0088 (11) |
C31 | 0.0373 (6) | 0.0343 (6) | 0.0318 (7) | −0.0043 (5) | 0.0119 (5) | −0.0014 (5) |
C32 | 0.0437 (7) | 0.0454 (7) | 0.0371 (7) | 0.0048 (5) | 0.0165 (6) | −0.0029 (6) |
C33 | 0.0371 (7) | 0.0497 (8) | 0.0402 (8) | 0.0052 (6) | 0.0086 (6) | 0.0023 (6) |
C34 | 0.0392 (7) | 0.0411 (7) | 0.0311 (6) | −0.0106 (5) | 0.0093 (5) | −0.0014 (5) |
C35 | 0.0405 (7) | 0.0435 (7) | 0.0375 (7) | −0.0041 (5) | 0.0162 (6) | −0.0115 (6) |
C36 | 0.0346 (6) | 0.0407 (7) | 0.0380 (7) | 0.0009 (5) | 0.0086 (5) | −0.0050 (6) |
C37 | 0.0433 (7) | 0.0375 (6) | 0.0326 (7) | −0.0062 (5) | 0.0108 (6) | −0.0023 (5) |
O31 | 0.0634 (7) | 0.0731 (7) | 0.0387 (6) | 0.0183 (5) | −0.0053 (5) | −0.0091 (5) |
O32 | 0.0664 (7) | 0.0579 (6) | 0.0364 (5) | 0.0017 (5) | 0.0197 (5) | −0.0099 (4) |
N34 | 0.0537 (8) | 0.0590 (8) | 0.0337 (6) | −0.0036 (6) | 0.0067 (5) | −0.0047 (6) |
N1—C2 | 1.4864 (18) | C24—H24 | 0.9300 |
N1—C6 | 1.4875 (18) | C25—C26 | 1.389 (2) |
N1—H11 | 1.067 (14) | C25—H25 | 0.9300 |
N1—H12 | 0.942 (15) | C26—H26 | 0.9300 |
C2—C3 | 1.4997 (16) | O22—C27 | 1.4228 (18) |
C2—H2A | 0.9700 | C27—H27A | 0.9600 |
C2—H2B | 0.9700 | C27—H27B | 0.9600 |
C3—N4 | 1.4768 (15) | C27—H27C | 0.9600 |
C3—H3A | 0.9700 | C31—C36 | 1.3844 (17) |
C3—H3B | 0.9700 | C31—C32 | 1.3897 (17) |
N4—C21 | 1.4235 (16) | C31—C37 | 1.4982 (16) |
N4—C5 | 1.4654 (16) | C32—C33 | 1.3796 (18) |
C5—C6 | 1.5067 (18) | C32—H32 | 0.9300 |
C5—H5A | 0.9700 | C33—C34 | 1.3902 (18) |
C5—H5B | 0.9700 | C33—H33 | 0.9300 |
C6—H6A | 0.9700 | C34—N34 | 1.3881 (16) |
C6—H6B | 0.9700 | C34—C35 | 1.3923 (18) |
C21—C26 | 1.380 (2) | C35—C36 | 1.3784 (17) |
C21—C22 | 1.4079 (19) | C35—H35 | 0.9300 |
C22—O22 | 1.3627 (17) | C36—H36 | 0.9300 |
C22—C23 | 1.3863 (19) | C37—O31 | 1.2506 (16) |
C23—C24 | 1.371 (2) | C37—O32 | 1.2542 (15) |
C23—H23 | 0.9300 | N34—H341 | 0.877 (16) |
C24—C25 | 1.363 (2) | N34—H342 | 0.913 (16) |
C2—N1—C6 | 109.66 (10) | C22—C23—H23 | 119.8 |
C2—N1—H11 | 107.7 (8) | C25—C24—C23 | 120.16 (15) |
C6—N1—H11 | 111.5 (7) | C25—C24—H24 | 119.9 |
C2—N1—H12 | 108.2 (9) | C23—C24—H24 | 119.9 |
C6—N1—H12 | 108.3 (9) | C24—C25—C26 | 120.10 (16) |
H11—N1—H12 | 111.5 (11) | C24—C25—H25 | 119.9 |
N1—C2—C3 | 110.42 (11) | C26—C25—H25 | 120.0 |
N1—C2—H2A | 109.6 | C21—C26—C25 | 121.33 (15) |
C3—C2—H2A | 109.6 | C21—C26—H26 | 119.3 |
N1—C2—H2B | 109.6 | C25—C26—H26 | 119.3 |
C3—C2—H2B | 109.6 | C22—O22—C27 | 117.90 (12) |
H2A—C2—H2B | 108.1 | O22—C27—H27A | 109.5 |
N4—C3—C2 | 110.62 (10) | O22—C27—H27B | 109.5 |
N4—C3—H3A | 109.5 | H27A—C27—H27B | 109.5 |
C2—C3—H3A | 109.5 | O22—C27—H27C | 109.5 |
N4—C3—H3B | 109.5 | H27A—C27—H27C | 109.5 |
C2—C3—H3B | 109.5 | H27B—C27—H27C | 109.5 |
H3A—C3—H3B | 108.1 | C36—C31—C32 | 117.75 (11) |
C21—N4—C5 | 115.29 (10) | C36—C31—C37 | 120.43 (11) |
C21—N4—C3 | 111.66 (9) | C32—C31—C37 | 121.82 (11) |
C5—N4—C3 | 109.81 (9) | C33—C32—C31 | 121.46 (12) |
N4—C5—C6 | 110.91 (11) | C33—C32—H32 | 119.3 |
N4—C5—H5A | 109.5 | C31—C32—H32 | 119.3 |
C6—C5—H5A | 109.5 | C32—C33—C34 | 120.54 (12) |
N4—C5—H5B | 109.5 | C32—C33—H33 | 119.7 |
C6—C5—H5B | 109.5 | C34—C33—H33 | 119.7 |
H5A—C5—H5B | 108.0 | N34—C34—C33 | 121.17 (12) |
N1—C6—C5 | 110.38 (10) | N34—C34—C35 | 120.69 (12) |
N1—C6—H6A | 109.6 | C33—C34—C35 | 118.11 (11) |
C5—C6—H6A | 109.6 | C36—C35—C34 | 120.86 (11) |
N1—C6—H6B | 109.6 | C36—C35—H35 | 119.6 |
C5—C6—H6B | 109.6 | C34—C35—H35 | 119.6 |
H6A—C6—H6B | 108.1 | C35—C36—C31 | 121.27 (12) |
C26—C21—C22 | 117.66 (13) | C35—C36—H36 | 119.4 |
C26—C21—N4 | 123.51 (12) | C31—C36—H36 | 119.4 |
C22—C21—N4 | 118.83 (12) | O31—C37—O32 | 124.36 (12) |
O22—C22—C23 | 123.91 (13) | O31—C37—C31 | 117.02 (11) |
O22—C22—C21 | 115.81 (12) | O32—C37—C31 | 118.62 (11) |
C23—C22—C21 | 120.28 (14) | C34—N34—H341 | 111.8 (11) |
C24—C23—C22 | 120.38 (15) | C34—N34—H342 | 114.2 (10) |
C24—C23—H23 | 119.8 | H341—N34—H342 | 120.4 (15) |
C6—N1—C2—C3 | −57.43 (14) | C22—C21—C26—C25 | 2.1 (2) |
N1—C2—C3—N4 | 58.53 (13) | N4—C21—C26—C25 | −177.79 (13) |
C2—C3—N4—C21 | 172.34 (11) | C24—C25—C26—C21 | 0.6 (3) |
C2—C3—N4—C5 | −58.48 (13) | C23—C22—O22—C27 | −7.6 (2) |
C21—N4—C5—C6 | −174.66 (10) | C21—C22—O22—C27 | 172.72 (13) |
C3—N4—C5—C6 | 58.16 (13) | C36—C31—C32—C33 | 0.31 (19) |
C2—N1—C6—C5 | 56.92 (14) | C37—C31—C32—C33 | 179.98 (12) |
N4—C5—C6—N1 | −57.96 (14) | C31—C32—C33—C34 | −0.6 (2) |
C5—N4—C21—C26 | −10.87 (18) | C32—C33—C34—N34 | 178.21 (12) |
C3—N4—C21—C26 | 115.36 (14) | C32—C33—C34—C35 | 0.14 (19) |
C5—N4—C21—C22 | 169.26 (11) | N34—C34—C35—C36 | −177.43 (12) |
C3—N4—C21—C22 | −64.51 (14) | C33—C34—C35—C36 | 0.65 (19) |
C26—C21—C22—O22 | 176.36 (13) | C34—C35—C36—C31 | −0.97 (19) |
N4—C21—C22—O22 | −3.76 (17) | C32—C31—C36—C35 | 0.48 (19) |
C26—C21—C22—C23 | −3.3 (2) | C37—C31—C36—C35 | −179.20 (11) |
N4—C21—C22—C23 | 176.56 (11) | C36—C31—C37—O31 | −3.44 (17) |
O22—C22—C23—C24 | −177.72 (15) | C32—C31—C37—O31 | 176.90 (13) |
C21—C22—C23—C24 | 1.9 (2) | C36—C31—C37—O32 | 177.29 (12) |
C22—C23—C24—C25 | 0.8 (3) | C32—C31—C37—O32 | −2.37 (18) |
C23—C24—C25—C26 | −2.1 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H11···O31 | 1.068 (15) | 1.547 (15) | 2.6048 (15) | 169.7 (14) |
N1—H12···O32i | 0.942 (15) | 1.861 (15) | 2.7797 (15) | 164.4 (14) |
N34—H342···O32ii | 0.914 (16) | 2.155 (16) | 3.0535 (18) | 167.5 (14) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, −y+1/2, z−1/2. |
C11H17N2O+·C7H4NO4− | F(000) = 760 |
Mr = 359.38 | Dx = 1.344 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 7.5174 (5) Å | Cell parameters from 3934 reflections |
b = 7.9761 (5) Å | θ = 2.7–27.9° |
c = 29.860 (2) Å | µ = 0.10 mm−1 |
β = 97.322 (6)° | T = 296 K |
V = 1775.8 (2) Å3 | Block, yellow |
Z = 4 | 0.50 × 0.50 × 0.40 mm |
Oxford Diffraction Xcalibur with Sapphire CCD diffractometer | 3934 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 2879 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.019 |
ω scans | θmax = 27.9°, θmin = 2.7° |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | h = −9→8 |
Tmin = 0.855, Tmax = 0.961 | k = −10→10 |
13660 measured reflections | l = −38→38 |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.040 | w = 1/[σ2(Fo2) + (0.0457P)2 + 0.4848P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.111 | (Δ/σ)max = 0.001 |
S = 1.03 | Δρmax = 0.17 e Å−3 |
3934 reflections | Δρmin = −0.15 e Å−3 |
242 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0175 (15) |
Primary atom site location: difference Fourier map |
Experimental. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. |
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 | ||
N1 | 0.44452 (18) | 0.51582 (18) | 0.42036 (4) | 0.0456 (3) | |
H11 | 0.359 (2) | 0.579 (2) | 0.4356 (6) | 0.055* | |
H12 | 0.486 (2) | 0.426 (2) | 0.4397 (6) | 0.055* | |
C2 | 0.5986 (2) | 0.6202 (2) | 0.41168 (5) | 0.0509 (4) | |
H2A | 0.6633 | 0.6571 | 0.4402 | 0.061* | |
H2B | 0.5558 | 0.7188 | 0.3946 | 0.061* | |
C3 | 0.72308 (19) | 0.5222 (2) | 0.38567 (5) | 0.0445 (4) | |
H3A | 0.8229 | 0.5926 | 0.3799 | 0.053* | |
H3B | 0.7707 | 0.4266 | 0.4034 | 0.053* | |
N4 | 0.62657 (15) | 0.46482 (15) | 0.34309 (4) | 0.0388 (3) | |
C5 | 0.47731 (19) | 0.3566 (2) | 0.35153 (5) | 0.0431 (3) | |
H5A | 0.5234 | 0.2588 | 0.3685 | 0.052* | |
H5B | 0.4140 | 0.3187 | 0.3230 | 0.052* | |
C6 | 0.3495 (2) | 0.4492 (2) | 0.37760 (5) | 0.0468 (4) | |
H6A | 0.2950 | 0.5410 | 0.3595 | 0.056* | |
H6B | 0.2548 | 0.3740 | 0.3841 | 0.056* | |
C21 | 0.73290 (19) | 0.39011 (18) | 0.31211 (5) | 0.0405 (3) | |
C22 | 0.6595 (2) | 0.3763 (2) | 0.26645 (5) | 0.0474 (4) | |
C23 | 0.7580 (3) | 0.3012 (2) | 0.23580 (6) | 0.0602 (5) | |
H23 | 0.7093 | 0.2922 | 0.2057 | 0.072* | |
C24 | 0.9269 (3) | 0.2400 (3) | 0.24948 (7) | 0.0697 (5) | |
H24 | 0.9919 | 0.1898 | 0.2286 | 0.084* | |
C25 | 1.0000 (2) | 0.2525 (3) | 0.29365 (7) | 0.0695 (5) | |
H25 | 1.1143 | 0.2108 | 0.3029 | 0.083* | |
C26 | 0.9025 (2) | 0.3280 (2) | 0.32471 (6) | 0.0546 (4) | |
H26 | 0.9533 | 0.3368 | 0.3547 | 0.066* | |
O22 | 0.49191 (17) | 0.43933 (18) | 0.25585 (4) | 0.0657 (4) | |
C27 | 0.4027 (3) | 0.4122 (3) | 0.21158 (6) | 0.0739 (6) | |
H27A | 0.2862 | 0.4633 | 0.2088 | 0.111* | |
H27B | 0.4715 | 0.4612 | 0.1900 | 0.111* | |
H27C | 0.3902 | 0.2940 | 0.2061 | 0.111* | |
C31 | 0.16123 (19) | 0.82005 (18) | 0.52883 (4) | 0.0392 (3) | |
C32 | −0.0213 (2) | 0.79178 (19) | 0.52353 (5) | 0.0450 (4) | |
H32 | −0.0716 | 0.7179 | 0.5014 | 0.054* | |
C33 | −0.1305 (2) | 0.8720 (2) | 0.55077 (5) | 0.0458 (4) | |
H33 | −0.2535 | 0.8531 | 0.5473 | 0.055* | |
C34 | −0.05131 (19) | 0.98058 (18) | 0.58316 (5) | 0.0414 (3) | |
C35 | 0.1295 (2) | 1.01111 (19) | 0.58934 (5) | 0.0441 (4) | |
H35 | 0.1794 | 1.0853 | 0.6115 | 0.053* | |
C36 | 0.2358 (2) | 0.92921 (19) | 0.56193 (5) | 0.0435 (3) | |
H36 | 0.3590 | 0.9477 | 0.5658 | 0.052* | |
C37 | 0.2801 (2) | 0.73155 (19) | 0.49920 (5) | 0.0458 (4) | |
O31 | 0.20537 (17) | 0.67769 (17) | 0.46209 (4) | 0.0656 (4) | |
O32 | 0.44235 (15) | 0.71810 (15) | 0.51349 (4) | 0.0570 (3) | |
N34 | −0.1638 (2) | 1.06966 (19) | 0.61219 (5) | 0.0541 (4) | |
O41 | −0.32042 (19) | 1.0270 (2) | 0.61086 (5) | 0.0826 (4) | |
O42 | −0.09646 (19) | 1.18199 (18) | 0.63615 (4) | 0.0731 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0481 (7) | 0.0554 (8) | 0.0341 (6) | 0.0041 (6) | 0.0078 (5) | −0.0034 (6) |
C2 | 0.0574 (9) | 0.0535 (9) | 0.0410 (8) | −0.0073 (8) | 0.0034 (7) | −0.0110 (7) |
C3 | 0.0444 (8) | 0.0490 (9) | 0.0395 (7) | −0.0089 (7) | 0.0027 (6) | −0.0033 (7) |
N4 | 0.0394 (6) | 0.0450 (7) | 0.0321 (6) | −0.0041 (5) | 0.0041 (5) | −0.0029 (5) |
C5 | 0.0409 (8) | 0.0510 (9) | 0.0372 (7) | −0.0061 (7) | 0.0039 (6) | −0.0064 (6) |
C6 | 0.0412 (8) | 0.0611 (10) | 0.0377 (7) | −0.0022 (7) | 0.0038 (6) | −0.0026 (7) |
C21 | 0.0424 (8) | 0.0419 (8) | 0.0383 (7) | −0.0049 (6) | 0.0089 (6) | −0.0004 (6) |
C22 | 0.0532 (9) | 0.0523 (9) | 0.0375 (7) | 0.0025 (7) | 0.0093 (6) | 0.0007 (7) |
C23 | 0.0696 (11) | 0.0717 (12) | 0.0422 (9) | 0.0004 (9) | 0.0182 (8) | −0.0069 (8) |
C24 | 0.0610 (11) | 0.0838 (14) | 0.0703 (12) | −0.0019 (10) | 0.0314 (10) | −0.0169 (11) |
C25 | 0.0408 (9) | 0.0878 (14) | 0.0816 (13) | 0.0024 (9) | 0.0144 (9) | −0.0132 (11) |
C26 | 0.0400 (8) | 0.0695 (11) | 0.0543 (9) | −0.0039 (8) | 0.0058 (7) | −0.0040 (8) |
O22 | 0.0696 (7) | 0.0899 (10) | 0.0349 (6) | 0.0288 (7) | −0.0039 (5) | −0.0076 (6) |
C27 | 0.0843 (13) | 0.0919 (15) | 0.0406 (9) | 0.0168 (12) | −0.0106 (9) | −0.0046 (9) |
C31 | 0.0456 (8) | 0.0401 (8) | 0.0318 (7) | 0.0060 (6) | 0.0049 (6) | 0.0060 (6) |
C32 | 0.0504 (9) | 0.0470 (8) | 0.0359 (7) | −0.0014 (7) | −0.0010 (6) | 0.0003 (6) |
C33 | 0.0392 (8) | 0.0526 (9) | 0.0454 (8) | −0.0017 (7) | 0.0052 (6) | 0.0076 (7) |
C34 | 0.0467 (8) | 0.0430 (8) | 0.0360 (7) | 0.0057 (7) | 0.0121 (6) | 0.0071 (6) |
C35 | 0.0498 (9) | 0.0438 (8) | 0.0385 (7) | −0.0012 (7) | 0.0044 (6) | −0.0019 (6) |
C36 | 0.0402 (8) | 0.0468 (8) | 0.0432 (8) | 0.0014 (7) | 0.0046 (6) | 0.0019 (7) |
C37 | 0.0556 (9) | 0.0455 (8) | 0.0372 (7) | 0.0100 (7) | 0.0089 (7) | 0.0053 (7) |
O31 | 0.0698 (8) | 0.0835 (9) | 0.0428 (6) | 0.0201 (7) | 0.0044 (6) | −0.0148 (6) |
O32 | 0.0520 (7) | 0.0674 (8) | 0.0526 (7) | 0.0152 (6) | 0.0111 (5) | 0.0023 (6) |
N34 | 0.0606 (9) | 0.0598 (9) | 0.0456 (7) | 0.0109 (7) | 0.0207 (6) | 0.0082 (7) |
O41 | 0.0611 (8) | 0.1020 (11) | 0.0923 (10) | 0.0029 (8) | 0.0395 (7) | −0.0035 (9) |
O42 | 0.0905 (10) | 0.0772 (9) | 0.0558 (7) | 0.0075 (8) | 0.0258 (7) | −0.0159 (7) |
N1—C2 | 1.476 (2) | C24—H24 | 0.9300 |
N1—C6 | 1.4798 (18) | C25—C26 | 1.390 (2) |
N1—H11 | 0.974 (18) | C25—H25 | 0.9300 |
N1—H12 | 0.947 (18) | C26—H26 | 0.9300 |
C2—C3 | 1.508 (2) | O22—C27 | 1.4204 (19) |
C2—H2A | 0.9700 | C27—H27A | 0.9600 |
C2—H2B | 0.9700 | C27—H27B | 0.9600 |
C3—N4 | 1.4551 (17) | C27—H27C | 0.9600 |
C3—H3A | 0.9700 | C31—C32 | 1.380 (2) |
C3—H3B | 0.9700 | C31—C36 | 1.381 (2) |
N4—C21 | 1.4275 (18) | C31—C37 | 1.510 (2) |
N4—C5 | 1.4626 (18) | C32—C33 | 1.384 (2) |
C5—C6 | 1.505 (2) | C32—H32 | 0.9300 |
C5—H5A | 0.9700 | C33—C34 | 1.376 (2) |
C5—H5B | 0.9700 | C33—H33 | 0.9300 |
C6—H6A | 0.9700 | C34—C35 | 1.370 (2) |
C6—H6B | 0.9700 | C34—N34 | 1.4690 (19) |
C21—C26 | 1.375 (2) | C35—C36 | 1.379 (2) |
C21—C22 | 1.409 (2) | C35—H35 | 0.9300 |
C22—O22 | 1.3562 (19) | C36—H36 | 0.9300 |
C22—C23 | 1.384 (2) | C37—O32 | 1.2443 (18) |
C23—C24 | 1.373 (3) | C37—O31 | 1.2528 (19) |
C23—H23 | 0.9300 | N34—O42 | 1.2157 (19) |
C24—C25 | 1.366 (3) | N34—O41 | 1.2217 (19) |
C2—N1—C6 | 110.74 (11) | C22—C23—H23 | 119.7 |
C2—N1—H11 | 111.7 (10) | C25—C24—C23 | 120.23 (17) |
C6—N1—H11 | 108.4 (10) | C25—C24—H24 | 119.9 |
C2—N1—H12 | 109.0 (10) | C23—C24—H24 | 119.9 |
C6—N1—H12 | 109.8 (10) | C24—C25—C26 | 119.65 (17) |
H11—N1—H12 | 107.1 (14) | C24—C25—H25 | 120.2 |
N1—C2—C3 | 110.53 (13) | C26—C25—H25 | 120.2 |
N1—C2—H2A | 109.5 | C21—C26—C25 | 121.52 (16) |
C3—C2—H2A | 109.5 | C21—C26—H26 | 119.2 |
N1—C2—H2B | 109.5 | C25—C26—H26 | 119.2 |
C3—C2—H2B | 109.5 | C22—O22—C27 | 118.37 (13) |
H2A—C2—H2B | 108.1 | O22—C27—H27A | 109.5 |
N4—C3—C2 | 109.89 (12) | O22—C27—H27B | 109.5 |
N4—C3—H3A | 109.7 | H27A—C27—H27B | 109.5 |
C2—C3—H3A | 109.7 | O22—C27—H27C | 109.5 |
N4—C3—H3B | 109.7 | H27A—C27—H27C | 109.5 |
C2—C3—H3B | 109.7 | H27B—C27—H27C | 109.5 |
H3A—C3—H3B | 108.2 | C32—C31—C36 | 119.48 (13) |
C21—N4—C3 | 116.07 (11) | C32—C31—C37 | 120.70 (13) |
C21—N4—C5 | 111.75 (11) | C36—C31—C37 | 119.81 (13) |
C3—N4—C5 | 110.07 (11) | C31—C32—C33 | 120.84 (14) |
N4—C5—C6 | 110.72 (12) | C31—C32—H32 | 119.6 |
N4—C5—H5A | 109.5 | C33—C32—H32 | 119.6 |
C6—C5—H5A | 109.5 | C34—C33—C32 | 117.93 (14) |
N4—C5—H5B | 109.5 | C34—C33—H33 | 121.0 |
C6—C5—H5B | 109.5 | C32—C33—H33 | 121.0 |
H5A—C5—H5B | 108.1 | C35—C34—C33 | 122.65 (14) |
N1—C6—C5 | 110.67 (12) | C35—C34—N34 | 118.04 (14) |
N1—C6—H6A | 109.5 | C33—C34—N34 | 119.30 (14) |
C5—C6—H6A | 109.5 | C34—C35—C36 | 118.40 (14) |
N1—C6—H6B | 109.5 | C34—C35—H35 | 120.8 |
C5—C6—H6B | 109.5 | C36—C35—H35 | 120.8 |
H6A—C6—H6B | 108.1 | C35—C36—C31 | 120.68 (14) |
C26—C21—C22 | 118.14 (14) | C35—C36—H36 | 119.7 |
C26—C21—N4 | 123.33 (13) | C31—C36—H36 | 119.7 |
C22—C21—N4 | 118.52 (13) | O32—C37—O31 | 125.68 (14) |
O22—C22—C23 | 124.42 (14) | O32—C37—C31 | 117.82 (13) |
O22—C22—C21 | 115.75 (13) | O31—C37—C31 | 116.50 (14) |
C23—C22—C21 | 119.83 (15) | O42—N34—O41 | 123.48 (15) |
C24—C23—C22 | 120.63 (16) | O42—N34—C34 | 118.43 (14) |
C24—C23—H23 | 119.7 | O41—N34—C34 | 118.09 (15) |
C6—N1—C2—C3 | −55.83 (17) | C24—C25—C26—C21 | 0.4 (3) |
N1—C2—C3—N4 | 58.62 (16) | C23—C22—O22—C27 | 6.8 (3) |
C2—C3—N4—C21 | 171.70 (12) | C21—C22—O22—C27 | −172.93 (16) |
C2—C3—N4—C5 | −60.13 (16) | C36—C31—C32—C33 | 0.3 (2) |
C21—N4—C5—C6 | −170.14 (12) | C37—C31—C32—C33 | 179.66 (13) |
C3—N4—C5—C6 | 59.35 (15) | C31—C32—C33—C34 | 0.1 (2) |
C2—N1—C6—C5 | 54.67 (17) | C32—C33—C34—C35 | −0.2 (2) |
N4—C5—C6—N1 | −56.40 (16) | C32—C33—C34—N34 | 179.10 (13) |
C3—N4—C21—C26 | 19.2 (2) | C33—C34—C35—C36 | −0.1 (2) |
C5—N4—C21—C26 | −108.17 (16) | N34—C34—C35—C36 | −179.38 (13) |
C3—N4—C21—C22 | −162.02 (14) | C34—C35—C36—C31 | 0.5 (2) |
C5—N4—C21—C22 | 70.65 (17) | C32—C31—C36—C35 | −0.6 (2) |
C26—C21—C22—O22 | 179.94 (15) | C37—C31—C36—C35 | −179.95 (13) |
N4—C21—C22—O22 | 1.1 (2) | C32—C31—C37—O32 | −157.78 (15) |
C26—C21—C22—C23 | 0.2 (2) | C36—C31—C37—O32 | 21.5 (2) |
N4—C21—C22—C23 | −178.64 (15) | C32—C31—C37—O31 | 22.1 (2) |
O22—C22—C23—C24 | −179.71 (18) | C36—C31—C37—O31 | −158.53 (15) |
C21—C22—C23—C24 | 0.0 (3) | C35—C34—N34—O42 | 9.5 (2) |
C22—C23—C24—C25 | 0.0 (3) | C33—C34—N34—O42 | −169.80 (14) |
C23—C24—C25—C26 | −0.1 (3) | C35—C34—N34—O41 | −170.64 (15) |
C22—C21—C26—C25 | −0.4 (3) | C33—C34—N34—O41 | 10.0 (2) |
N4—C21—C26—C25 | 178.42 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H11···O31 | 0.974 (16) | 1.677 (16) | 2.6500 (19) | 176.8 (15) |
N1—H11···O32 | 0.974 (16) | 2.581 (17) | 3.2169 (17) | 123.0 (12) |
N1—H12···O32i | 0.948 (17) | 1.837 (17) | 2.7709 (18) | 168.2 (16) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
C11H17N2O+·C7H3N2O6−·2H2O | Z = 2 |
Mr = 440.41 | F(000) = 464 |
Triclinic, P1 | Dx = 1.405 Mg m−3 |
a = 7.8448 (6) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.4635 (9) Å | Cell parameters from 4419 reflections |
c = 12.0747 (9) Å | θ = 2.6–27.7° |
α = 94.406 (7)° | µ = 0.11 mm−1 |
β = 105.075 (8)° | T = 296 K |
γ = 93.717 (7)° | Block, yellow |
V = 1041.33 (14) Å3 | 0.48 × 0.48 × 0.44 mm |
Oxford Diffraction Xcalibur with Sapphire CCD diffractometer | 4419 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 3409 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.016 |
ω scans | θmax = 27.7°, θmin = 2.6° |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | h = −9→10 |
Tmin = 0.892, Tmax = 0.951 | k = −9→14 |
7353 measured reflections | l = −15→14 |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.039 | w = 1/[σ2(Fo2) + (0.0554P)2 + 0.1343P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.108 | (Δ/σ)max < 0.001 |
S = 1.06 | Δρmax = 0.23 e Å−3 |
4419 reflections | Δρmin = −0.17 e Å−3 |
300 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.052 (4) |
Primary atom site location: difference Fourier map |
Experimental. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. |
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 | ||
N1 | 0.65966 (17) | 0.38158 (10) | 0.34243 (10) | 0.0387 (3) | |
H11 | 0.718 (2) | 0.3310 (14) | 0.3931 (14) | 0.046* | |
H12 | 0.541 (2) | 0.3638 (13) | 0.3304 (13) | 0.046* | |
C2 | 0.7170 (2) | 0.37246 (12) | 0.23459 (12) | 0.0437 (3) | |
H2A | 0.6800 | 0.2946 | 0.1947 | 0.052* | |
H2B | 0.8452 | 0.3838 | 0.2531 | 0.052* | |
C3 | 0.63768 (19) | 0.46357 (11) | 0.15669 (11) | 0.0383 (3) | |
H3A | 0.6811 | 0.4588 | 0.0884 | 0.046* | |
H3B | 0.5097 | 0.4481 | 0.1325 | 0.046* | |
N4 | 0.68560 (14) | 0.58186 (8) | 0.21770 (8) | 0.0317 (2) | |
C5 | 0.61652 (19) | 0.58963 (11) | 0.31932 (11) | 0.0374 (3) | |
H5A | 0.4888 | 0.5723 | 0.2961 | 0.045* | |
H5B | 0.6431 | 0.6686 | 0.3579 | 0.045* | |
C6 | 0.7004 (2) | 0.50306 (12) | 0.40043 (11) | 0.0422 (3) | |
H6A | 0.8278 | 0.5219 | 0.4251 | 0.051* | |
H6B | 0.6557 | 0.5085 | 0.4682 | 0.051* | |
C21 | 0.64076 (16) | 0.67242 (10) | 0.14284 (10) | 0.0311 (3) | |
C22 | 0.74860 (16) | 0.69609 (11) | 0.06906 (11) | 0.0342 (3) | |
C23 | 0.71254 (19) | 0.78402 (12) | −0.00441 (12) | 0.0421 (3) | |
H23 | 0.7837 | 0.7991 | −0.0533 | 0.051* | |
C24 | 0.5696 (2) | 0.84922 (12) | −0.00446 (13) | 0.0466 (4) | |
H24 | 0.5458 | 0.9083 | −0.0535 | 0.056* | |
C25 | 0.4631 (2) | 0.82783 (12) | 0.06667 (13) | 0.0476 (4) | |
H25 | 0.3677 | 0.8721 | 0.0660 | 0.057* | |
C26 | 0.49877 (18) | 0.73919 (12) | 0.14005 (12) | 0.0399 (3) | |
H26 | 0.4260 | 0.7245 | 0.1881 | 0.048* | |
O22 | 0.88764 (13) | 0.62807 (9) | 0.07539 (9) | 0.0471 (3) | |
C27 | 1.0094 (2) | 0.65658 (16) | 0.01004 (16) | 0.0601 (4) | |
H27A | 1.1050 | 0.6069 | 0.0266 | 0.090* | |
H27B | 1.0556 | 0.7372 | 0.0301 | 0.090* | |
H27C | 0.9495 | 0.6448 | −0.0706 | 0.090* | |
C31 | 1.07262 (16) | 0.14162 (10) | 0.58115 (10) | 0.0328 (3) | |
C32 | 1.23171 (17) | 0.09894 (11) | 0.57551 (11) | 0.0361 (3) | |
H32 | 1.2888 | 0.1233 | 0.5216 | 0.043* | |
C33 | 1.30429 (17) | 0.01961 (11) | 0.65116 (12) | 0.0384 (3) | |
C34 | 1.22367 (18) | −0.02069 (11) | 0.73110 (12) | 0.0406 (3) | |
H34 | 1.2719 | −0.0765 | 0.7792 | 0.049* | |
C35 | 1.06862 (18) | 0.02555 (11) | 0.73629 (11) | 0.0376 (3) | |
C36 | 0.99163 (17) | 0.10646 (11) | 0.66424 (11) | 0.0356 (3) | |
H36 | 0.8874 | 0.1369 | 0.6712 | 0.043* | |
C37 | 0.98662 (19) | 0.22652 (11) | 0.49671 (11) | 0.0402 (3) | |
O31 | 0.84578 (15) | 0.26458 (10) | 0.51102 (9) | 0.0585 (3) | |
O32 | 1.05696 (16) | 0.24991 (11) | 0.42026 (10) | 0.0655 (3) | |
N33 | 1.47682 (18) | −0.02225 (14) | 0.64945 (12) | 0.0578 (4) | |
O33 | 1.57628 (16) | 0.04182 (15) | 0.61300 (12) | 0.0825 (4) | |
O34 | 1.51295 (19) | −0.11651 (13) | 0.68590 (15) | 0.0890 (5) | |
N35 | 0.98229 (19) | −0.01443 (13) | 0.82304 (11) | 0.0558 (4) | |
O35 | 1.0381 (2) | −0.09880 (14) | 0.87252 (13) | 0.0929 (5) | |
O36 | 0.86187 (19) | 0.03867 (14) | 0.84155 (11) | 0.0794 (4) | |
O41 | 0.28832 (16) | 0.36547 (12) | 0.31241 (12) | 0.0639 (3) | |
H41 | 0.225 (3) | 0.322 (2) | 0.341 (2) | 0.096* | |
H42 | 0.230 (3) | 0.431 (2) | 0.306 (2) | 0.096* | |
O51 | 0.13836 (19) | 0.58148 (13) | 0.29313 (13) | 0.0722 (4) | |
H51 | 0.152 (3) | 0.630 (2) | 0.356 (2) | 0.087* | |
H52 | 0.051 (3) | 0.593 (2) | 0.250 (2) | 0.087* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0413 (6) | 0.0353 (6) | 0.0404 (6) | 0.0049 (5) | 0.0087 (5) | 0.0154 (5) |
C2 | 0.0584 (9) | 0.0332 (7) | 0.0429 (7) | 0.0107 (6) | 0.0162 (6) | 0.0094 (6) |
C3 | 0.0516 (8) | 0.0308 (6) | 0.0324 (6) | 0.0051 (5) | 0.0098 (6) | 0.0057 (5) |
N4 | 0.0371 (6) | 0.0279 (5) | 0.0311 (5) | 0.0029 (4) | 0.0096 (4) | 0.0077 (4) |
C5 | 0.0470 (8) | 0.0315 (6) | 0.0363 (7) | 0.0019 (5) | 0.0155 (6) | 0.0049 (5) |
C6 | 0.0536 (8) | 0.0414 (7) | 0.0320 (6) | 0.0004 (6) | 0.0118 (6) | 0.0079 (5) |
C21 | 0.0327 (6) | 0.0270 (6) | 0.0318 (6) | 0.0005 (5) | 0.0052 (5) | 0.0060 (5) |
C22 | 0.0338 (6) | 0.0321 (6) | 0.0365 (7) | 0.0022 (5) | 0.0077 (5) | 0.0080 (5) |
C23 | 0.0484 (8) | 0.0401 (7) | 0.0390 (7) | 0.0001 (6) | 0.0115 (6) | 0.0141 (6) |
C24 | 0.0540 (9) | 0.0357 (7) | 0.0460 (8) | 0.0060 (6) | 0.0022 (7) | 0.0161 (6) |
C25 | 0.0445 (8) | 0.0382 (7) | 0.0580 (9) | 0.0130 (6) | 0.0057 (7) | 0.0111 (6) |
C26 | 0.0375 (7) | 0.0381 (7) | 0.0459 (7) | 0.0054 (5) | 0.0125 (6) | 0.0087 (6) |
O22 | 0.0455 (6) | 0.0506 (6) | 0.0572 (6) | 0.0148 (4) | 0.0270 (5) | 0.0240 (5) |
C27 | 0.0554 (10) | 0.0656 (10) | 0.0750 (11) | 0.0128 (8) | 0.0392 (9) | 0.0226 (9) |
C31 | 0.0363 (7) | 0.0269 (6) | 0.0337 (6) | −0.0015 (5) | 0.0072 (5) | 0.0046 (5) |
C32 | 0.0371 (7) | 0.0359 (6) | 0.0353 (6) | −0.0037 (5) | 0.0113 (5) | 0.0042 (5) |
C33 | 0.0327 (7) | 0.0377 (7) | 0.0425 (7) | 0.0049 (5) | 0.0064 (5) | 0.0007 (6) |
C34 | 0.0440 (8) | 0.0335 (7) | 0.0413 (7) | 0.0048 (5) | 0.0038 (6) | 0.0107 (6) |
C35 | 0.0418 (7) | 0.0367 (7) | 0.0347 (7) | −0.0030 (5) | 0.0107 (5) | 0.0100 (5) |
C36 | 0.0340 (7) | 0.0360 (6) | 0.0375 (7) | 0.0032 (5) | 0.0099 (5) | 0.0070 (5) |
C37 | 0.0465 (8) | 0.0338 (7) | 0.0375 (7) | −0.0006 (6) | 0.0055 (6) | 0.0098 (5) |
O31 | 0.0658 (7) | 0.0649 (7) | 0.0502 (6) | 0.0306 (6) | 0.0137 (5) | 0.0242 (5) |
O32 | 0.0711 (8) | 0.0732 (8) | 0.0619 (7) | 0.0061 (6) | 0.0257 (6) | 0.0399 (6) |
N33 | 0.0409 (7) | 0.0721 (10) | 0.0583 (8) | 0.0138 (7) | 0.0086 (6) | 0.0005 (7) |
O33 | 0.0407 (7) | 0.1309 (13) | 0.0809 (9) | 0.0122 (7) | 0.0210 (6) | 0.0204 (9) |
O34 | 0.0697 (9) | 0.0731 (9) | 0.1238 (13) | 0.0407 (7) | 0.0150 (8) | 0.0152 (8) |
N35 | 0.0564 (8) | 0.0689 (9) | 0.0457 (7) | −0.0032 (7) | 0.0170 (6) | 0.0226 (6) |
O35 | 0.1110 (12) | 0.0950 (11) | 0.0922 (10) | 0.0168 (9) | 0.0434 (9) | 0.0664 (9) |
O36 | 0.0691 (8) | 0.1213 (12) | 0.0645 (8) | 0.0177 (8) | 0.0387 (7) | 0.0319 (8) |
O41 | 0.0520 (7) | 0.0584 (7) | 0.0919 (9) | 0.0049 (5) | 0.0336 (6) | 0.0231 (7) |
O51 | 0.0665 (8) | 0.0786 (9) | 0.0674 (8) | 0.0321 (7) | 0.0051 (7) | 0.0044 (7) |
N1—C2 | 1.4826 (18) | C26—H26 | 0.9300 |
N1—C6 | 1.4860 (18) | O22—C27 | 1.4257 (17) |
N1—H11 | 0.929 (16) | C27—H27A | 0.9600 |
N1—H12 | 0.908 (16) | C27—H27B | 0.9600 |
C2—C3 | 1.5143 (17) | C27—H27C | 0.9600 |
C2—H2A | 0.9700 | C31—C32 | 1.3856 (19) |
C2—H2B | 0.9700 | C31—C36 | 1.3903 (17) |
C3—N4 | 1.4694 (16) | C31—C37 | 1.5237 (17) |
C3—H3A | 0.9700 | C32—C33 | 1.3820 (18) |
C3—H3B | 0.9700 | C32—H32 | 0.9300 |
N4—C21 | 1.4300 (15) | C33—C34 | 1.3759 (19) |
N4—C5 | 1.4638 (16) | C33—N33 | 1.4696 (19) |
C5—C6 | 1.5086 (18) | C34—C35 | 1.372 (2) |
C5—H5A | 0.9700 | C34—H34 | 0.9300 |
C5—H5B | 0.9700 | C35—C36 | 1.3803 (17) |
C6—H6A | 0.9700 | C35—N35 | 1.4727 (17) |
C6—H6B | 0.9700 | C36—H36 | 0.9300 |
C21—C26 | 1.3866 (18) | C37—O32 | 1.2297 (17) |
C21—C22 | 1.4080 (17) | C37—O31 | 1.2615 (18) |
C22—O22 | 1.3709 (16) | N33—O34 | 1.2204 (19) |
C22—C23 | 1.3881 (17) | N33—O33 | 1.2231 (19) |
C23—C24 | 1.387 (2) | N35—O36 | 1.2150 (19) |
C23—H23 | 0.9300 | N35—O35 | 1.2214 (18) |
C24—C25 | 1.369 (2) | O41—H41 | 0.84 (2) |
C24—H24 | 0.9300 | O41—H42 | 0.91 (3) |
C25—C26 | 1.3936 (19) | O51—H51 | 0.88 (2) |
C25—H25 | 0.9300 | O51—H52 | 0.77 (2) |
C2—N1—C6 | 110.76 (10) | C23—C24—H24 | 119.5 |
C2—N1—H11 | 110.5 (10) | C24—C25—C26 | 119.49 (13) |
C6—N1—H11 | 108.2 (9) | C24—C25—H25 | 120.3 |
C2—N1—H12 | 113.0 (10) | C26—C25—H25 | 120.3 |
C6—N1—H12 | 106.6 (10) | C21—C26—C25 | 121.23 (13) |
H11—N1—H12 | 107.6 (13) | C21—C26—H26 | 119.4 |
N1—C2—C3 | 110.82 (11) | C25—C26—H26 | 119.4 |
N1—C2—H2A | 109.5 | C22—O22—C27 | 117.66 (11) |
C3—C2—H2A | 109.5 | O22—C27—H27A | 109.5 |
N1—C2—H2B | 109.5 | O22—C27—H27B | 109.5 |
C3—C2—H2B | 109.5 | H27A—C27—H27B | 109.5 |
H2A—C2—H2B | 108.1 | O22—C27—H27C | 109.5 |
N4—C3—C2 | 110.21 (10) | H27A—C27—H27C | 109.5 |
N4—C3—H3A | 109.6 | H27B—C27—H27C | 109.5 |
C2—C3—H3A | 109.6 | C32—C31—C36 | 119.65 (11) |
N4—C3—H3B | 109.6 | C32—C31—C37 | 120.23 (11) |
C2—C3—H3B | 109.6 | C36—C31—C37 | 120.12 (12) |
H3A—C3—H3B | 108.1 | C33—C32—C31 | 118.99 (12) |
C21—N4—C5 | 115.30 (10) | C33—C32—H32 | 120.5 |
C21—N4—C3 | 112.57 (9) | C31—C32—H32 | 120.5 |
C5—N4—C3 | 109.48 (10) | C34—C33—C32 | 122.75 (12) |
N4—C5—C6 | 109.39 (11) | C34—C33—N33 | 117.76 (12) |
N4—C5—H5A | 109.8 | C32—C33—N33 | 119.48 (13) |
C6—C5—H5A | 109.8 | C35—C34—C33 | 116.72 (12) |
N4—C5—H5B | 109.8 | C35—C34—H34 | 121.6 |
C6—C5—H5B | 109.8 | C33—C34—H34 | 121.6 |
H5A—C5—H5B | 108.2 | C34—C35—C36 | 122.99 (12) |
N1—C6—C5 | 110.28 (11) | C34—C35—N35 | 117.58 (12) |
N1—C6—H6A | 109.6 | C36—C35—N35 | 119.42 (12) |
C5—C6—H6A | 109.6 | C35—C36—C31 | 118.82 (12) |
N1—C6—H6B | 109.6 | C35—C36—H36 | 120.6 |
C5—C6—H6B | 109.6 | C31—C36—H36 | 120.6 |
H6A—C6—H6B | 108.1 | O32—C37—O31 | 125.98 (13) |
C26—C21—C22 | 118.27 (11) | O32—C37—C31 | 118.05 (13) |
C26—C21—N4 | 123.70 (11) | O31—C37—C31 | 115.95 (12) |
C22—C21—N4 | 118.02 (11) | O34—N33—O33 | 124.40 (15) |
O22—C22—C23 | 123.48 (12) | O34—N33—C33 | 118.57 (15) |
O22—C22—C21 | 116.04 (10) | O33—N33—C33 | 117.02 (14) |
C23—C22—C21 | 120.48 (12) | O36—N35—O35 | 124.28 (14) |
C24—C23—C22 | 119.57 (13) | O36—N35—C35 | 118.33 (13) |
C24—C23—H23 | 120.2 | O35—N35—C35 | 117.39 (15) |
C22—C23—H23 | 120.2 | H41—O41—H42 | 102 (2) |
C25—C24—C23 | 120.95 (12) | H51—O51—H52 | 108 (2) |
C25—C24—H24 | 119.5 | ||
C6—N1—C2—C3 | −54.19 (15) | C36—C31—C32—C33 | 1.65 (18) |
N1—C2—C3—N4 | 56.54 (15) | C37—C31—C32—C33 | −178.27 (11) |
C2—C3—N4—C21 | 169.85 (11) | C31—C32—C33—C34 | 1.13 (19) |
C2—C3—N4—C5 | −60.51 (14) | C31—C32—C33—N33 | −177.30 (12) |
C21—N4—C5—C6 | −169.80 (10) | C32—C33—C34—C35 | −2.7 (2) |
C3—N4—C5—C6 | 62.06 (13) | N33—C33—C34—C35 | 175.77 (12) |
C2—N1—C6—C5 | 55.87 (15) | C33—C34—C35—C36 | 1.5 (2) |
N4—C5—C6—N1 | −59.79 (14) | C33—C34—C35—N35 | −178.66 (12) |
C5—N4—C21—C26 | −21.15 (17) | C34—C35—C36—C31 | 1.1 (2) |
C3—N4—C21—C26 | 105.44 (14) | N35—C35—C36—C31 | −178.69 (12) |
C5—N4—C21—C22 | 157.91 (11) | C32—C31—C36—C35 | −2.72 (18) |
C3—N4—C21—C22 | −75.51 (14) | C37—C31—C36—C35 | 177.21 (11) |
C26—C21—C22—O22 | 179.73 (11) | C32—C31—C37—O32 | 4.20 (18) |
N4—C21—C22—O22 | 0.62 (16) | C36—C31—C37—O32 | −175.73 (13) |
C26—C21—C22—C23 | −0.10 (18) | C32—C31—C37—O31 | −177.24 (13) |
N4—C21—C22—C23 | −179.21 (11) | C36—C31—C37—O31 | 2.83 (18) |
O22—C22—C23—C24 | −179.50 (13) | C34—C33—N33—O34 | 25.3 (2) |
C21—C22—C23—C24 | 0.3 (2) | C32—C33—N33—O34 | −156.20 (15) |
C22—C23—C24—C25 | −0.2 (2) | C34—C33—N33—O33 | −153.41 (14) |
C23—C24—C25—C26 | −0.1 (2) | C32—C33—N33—O33 | 25.1 (2) |
C22—C21—C26—C25 | −0.20 (19) | C34—C35—N35—O36 | 168.36 (14) |
N4—C21—C26—C25 | 178.85 (12) | C36—C35—N35—O36 | −11.8 (2) |
C24—C25—C26—C21 | 0.3 (2) | C34—C35—N35—O35 | −11.0 (2) |
C23—C22—O22—C27 | 5.6 (2) | C36—C35—N35—O35 | 168.77 (14) |
C21—C22—O22—C27 | −174.26 (12) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H11···O31 | 0.929 (16) | 1.771 (16) | 2.6837 (16) | 166.8 (15) |
N1—H12···O41 | 0.911 (16) | 1.939 (16) | 2.8324 (19) | 165.5 (14) |
O41—H41···O32i | 0.84 (2) | 1.99 (2) | 2.8156 (19) | 168 (2) |
O41—H42···O51 | 0.90 (2) | 1.91 (2) | 2.810 (2) | 172 (2) |
O51—H51···O31ii | 0.90 (2) | 1.91 (2) | 2.810 (2) | 172 (2) |
O51—H52···O22i | 0.77 (2) | 2.25 (2) | 2.9544 (19) | 153 (2) |
C25—H25···O36ii | 0.93 | 2.58 | 3.433 (2) | 153 |
Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+1, −z+1. |
C11H17N2O+·C6H2N3O7− | Z = 2 |
Mr = 421.33 | F(000) = 440 |
Triclinic, P1 | Dx = 1.435 Mg m−3 |
a = 9.4151 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.8721 (5) Å | Cell parameters from 4279 reflections |
c = 10.9572 (5) Å | θ = 2.9–27.8° |
α = 77.524 (4)° | µ = 0.12 mm−1 |
β = 81.360 (5)° | T = 296 K |
γ = 81.002 (5)° | Plate, orange |
V = 974.97 (9) Å3 | 0.48 × 0.48 × 0.24 mm |
Oxford Diffraction Xcalibur with Sapphire CCD diffractometer | 4279 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 3276 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.017 |
ω scans | θmax = 27.8°, θmin = 2.9° |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | h = −12→12 |
Tmin = 0.805, Tmax = 0.973 | k = −12→12 |
12926 measured reflections | l = −13→13 |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.040 | w = 1/[σ2(Fo2) + (0.0587P)2 + 0.1566P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.119 | (Δ/σ)max < 0.001 |
S = 1.07 | Δρmax = 0.24 e Å−3 |
4279 reflections | Δρmin = −0.27 e Å−3 |
317 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
85 restraints | Extinction coefficient: 0.021 (3) |
Primary atom site location: difference Fourier map |
Experimental. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. |
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) | |
N1 | 0.55402 (16) | 0.61143 (13) | 0.19946 (11) | 0.0462 (3) | |
H11 | 0.480 (2) | 0.5879 (18) | 0.2530 (16) | 0.055* | |
H12 | 0.6047 (19) | 0.6597 (18) | 0.2347 (16) | 0.055* | |
C2 | 0.64890 (19) | 0.48431 (16) | 0.17048 (14) | 0.0534 (4) | |
H2A | 0.5924 | 0.4256 | 0.1420 | 0.064* | |
H2B | 0.6880 | 0.4312 | 0.2461 | 0.064* | |
C3 | 0.77123 (17) | 0.52432 (16) | 0.07001 (13) | 0.0497 (4) | |
H3A | 0.8326 | 0.5761 | 0.1013 | 0.060* | |
H3B | 0.8296 | 0.4405 | 0.0492 | 0.060* | |
N4 | 0.71457 (12) | 0.61034 (12) | −0.04332 (10) | 0.0418 (3) | |
C5 | 0.62911 (16) | 0.73798 (15) | −0.01273 (13) | 0.0457 (3) | |
H5A | 0.5947 | 0.7967 | −0.0883 | 0.055* | |
H5B | 0.6891 | 0.7898 | 0.0201 | 0.055* | |
C6 | 0.50188 (16) | 0.70175 (17) | 0.08392 (14) | 0.0490 (4) | |
H6A | 0.4457 | 0.7868 | 0.1043 | 0.059* | |
H6B | 0.4398 | 0.6532 | 0.0499 | 0.059* | |
C21 | 0.82215 (14) | 0.63009 (17) | −0.14998 (13) | 0.0446 (3) | |
C22 | 0.87678 (16) | 0.51580 (19) | −0.20905 (14) | 0.0525 (4) | |
C23 | 0.97820 (18) | 0.5326 (2) | −0.31534 (16) | 0.0665 (5) | |
H23 | 1.0151 | 0.4568 | −0.3534 | 0.080* | |
C24 | 1.02430 (19) | 0.6610 (3) | −0.36469 (17) | 0.0741 (6) | |
H24 | 1.0912 | 0.6719 | −0.4366 | 0.089* | |
C25 | 0.97236 (19) | 0.7728 (2) | −0.30852 (19) | 0.0706 (5) | |
H25 | 1.0036 | 0.8594 | −0.3426 | 0.085* | |
C26 | 0.87250 (17) | 0.75717 (19) | −0.19997 (15) | 0.0556 (4) | |
H26 | 0.8396 | 0.8330 | −0.1610 | 0.067* | |
O22 | 0.82269 (13) | 0.39384 (13) | −0.15675 (12) | 0.0685 (4) | |
C27 | 0.8927 (2) | 0.2687 (2) | −0.1938 (2) | 0.0859 (7) | |
H27A | 0.8424 | 0.1918 | −0.1492 | 0.129* | |
H27B | 0.8921 | 0.2773 | −0.2827 | 0.129* | |
H27C | 0.9909 | 0.2521 | −0.1747 | 0.129* | |
C31 | 0.29075 (13) | 0.15664 (13) | 0.64803 (12) | 0.0362 (3) | |
O31 | 0.27727 (12) | 0.22396 (11) | 0.73386 (9) | 0.0512 (3) | |
C32 | 0.32774 (14) | 0.20872 (13) | 0.51527 (12) | 0.0361 (3) | |
N32 | 0.35214 (13) | 0.35445 (12) | 0.47084 (11) | 0.0445 (3) | |
O32 | 0.3202 (2) | 0.43611 (12) | 0.54139 (13) | 0.0911 (5) | |
O33 | 0.40574 (16) | 0.38892 (13) | 0.36249 (11) | 0.0705 (4) | |
C33 | 0.34703 (14) | 0.12760 (14) | 0.42520 (12) | 0.0381 (3) | |
H33 | 0.3709 | 0.1669 | 0.3409 | 0.046* | |
C34 | 0.33077 (14) | −0.01230 (14) | 0.46070 (13) | 0.0393 (3) | |
N34 | 0.35475 (14) | −0.09763 (14) | 0.36584 (13) | 0.0501 (3) | |
O34 | 0.38287 (16) | −0.04191 (13) | 0.25521 (11) | 0.0731 (4) | |
O35 | 0.34933 (15) | −0.22433 (12) | 0.40011 (12) | 0.0699 (4) | |
C35 | 0.29789 (14) | −0.07370 (14) | 0.58638 (13) | 0.0413 (3) | |
H35 | 0.2907 | −0.1689 | 0.6101 | 0.050* | |
C36 | 0.27649 (15) | 0.00877 (14) | 0.67410 (13) | 0.0404 (3) | |
N36 | 0.24422 (18) | −0.05867 (14) | 0.80615 (13) | 0.0590 (4) | 0.850 (5) |
O36 | 0.3154 (3) | −0.1672 (2) | 0.84426 (18) | 0.0830 (8) | 0.850 (5) |
O37 | 0.1395 (3) | −0.0058 (3) | 0.8665 (2) | 0.1155 (12) | 0.850 (5) |
N37 | 0.24422 (18) | −0.05867 (14) | 0.80615 (13) | 0.0590 (4) | 0.069 (4) |
O38 | 0.1277 (16) | −0.090 (3) | 0.853 (2) | 0.094 (5) | 0.069 (4) |
O39 | 0.3392 (18) | −0.077 (3) | 0.8764 (17) | 0.081 (5) | 0.069 (4) |
N38 | 0.24422 (18) | −0.05867 (14) | 0.80615 (13) | 0.0590 (4) | 0.080 (4) |
O310 | 0.219 (3) | −0.1764 (12) | 0.8390 (16) | 0.074 (4) | 0.080 (4) |
O311 | 0.275 (3) | −0.0034 (19) | 0.8882 (12) | 0.084 (5) | 0.080 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0592 (8) | 0.0466 (7) | 0.0358 (6) | −0.0182 (6) | 0.0091 (5) | −0.0164 (5) |
C2 | 0.0759 (11) | 0.0414 (8) | 0.0405 (8) | −0.0091 (7) | 0.0051 (7) | −0.0101 (6) |
C3 | 0.0557 (9) | 0.0483 (8) | 0.0401 (8) | 0.0020 (7) | −0.0023 (6) | −0.0066 (6) |
N4 | 0.0405 (6) | 0.0504 (7) | 0.0326 (6) | −0.0034 (5) | 0.0021 (5) | −0.0102 (5) |
C5 | 0.0490 (8) | 0.0473 (8) | 0.0384 (7) | −0.0022 (6) | −0.0017 (6) | −0.0083 (6) |
C6 | 0.0478 (8) | 0.0562 (9) | 0.0443 (8) | −0.0028 (7) | 0.0012 (6) | −0.0200 (7) |
C21 | 0.0335 (7) | 0.0627 (9) | 0.0359 (7) | −0.0058 (6) | −0.0026 (5) | −0.0075 (6) |
C22 | 0.0393 (7) | 0.0748 (11) | 0.0445 (8) | −0.0083 (7) | 0.0029 (6) | −0.0190 (7) |
C23 | 0.0459 (9) | 0.1026 (15) | 0.0524 (9) | −0.0098 (9) | 0.0095 (7) | −0.0289 (10) |
C24 | 0.0457 (9) | 0.1197 (18) | 0.0492 (10) | −0.0162 (10) | 0.0118 (7) | −0.0081 (11) |
C25 | 0.0446 (9) | 0.0875 (14) | 0.0697 (11) | −0.0201 (9) | 0.0023 (8) | 0.0086 (10) |
C26 | 0.0427 (8) | 0.0673 (10) | 0.0532 (9) | −0.0103 (7) | −0.0022 (7) | −0.0040 (8) |
O22 | 0.0631 (7) | 0.0668 (8) | 0.0754 (8) | −0.0114 (6) | 0.0235 (6) | −0.0334 (6) |
C27 | 0.0654 (12) | 0.0845 (14) | 0.1171 (18) | −0.0103 (10) | 0.0152 (12) | −0.0576 (13) |
C31 | 0.0339 (6) | 0.0377 (7) | 0.0377 (7) | −0.0051 (5) | −0.0007 (5) | −0.0108 (5) |
O31 | 0.0628 (7) | 0.0526 (6) | 0.0424 (5) | −0.0143 (5) | 0.0048 (5) | −0.0213 (5) |
C32 | 0.0350 (6) | 0.0334 (6) | 0.0394 (7) | −0.0052 (5) | −0.0022 (5) | −0.0074 (5) |
N32 | 0.0503 (7) | 0.0376 (6) | 0.0439 (7) | −0.0078 (5) | −0.0004 (5) | −0.0063 (5) |
O32 | 0.1554 (15) | 0.0395 (6) | 0.0721 (9) | −0.0210 (8) | 0.0280 (9) | −0.0198 (6) |
O33 | 0.1042 (10) | 0.0583 (7) | 0.0468 (6) | −0.0345 (7) | 0.0120 (6) | −0.0028 (5) |
C33 | 0.0364 (6) | 0.0435 (7) | 0.0342 (6) | −0.0030 (5) | −0.0035 (5) | −0.0092 (5) |
C34 | 0.0364 (7) | 0.0417 (7) | 0.0434 (7) | −0.0035 (5) | −0.0048 (5) | −0.0177 (6) |
N34 | 0.0508 (7) | 0.0505 (7) | 0.0550 (8) | −0.0020 (6) | −0.0089 (6) | −0.0249 (6) |
O34 | 0.1083 (11) | 0.0670 (8) | 0.0462 (7) | −0.0009 (7) | −0.0053 (6) | −0.0262 (6) |
O35 | 0.0909 (9) | 0.0500 (7) | 0.0782 (8) | −0.0137 (6) | −0.0071 (7) | −0.0319 (6) |
C35 | 0.0401 (7) | 0.0345 (7) | 0.0500 (8) | −0.0062 (5) | −0.0032 (6) | −0.0102 (6) |
C36 | 0.0411 (7) | 0.0395 (7) | 0.0382 (7) | −0.0061 (6) | 0.0004 (5) | −0.0050 (5) |
N36 | 0.0847 (11) | 0.0435 (8) | 0.0447 (8) | −0.0127 (7) | 0.0056 (7) | −0.0060 (6) |
O36 | 0.1144 (18) | 0.0577 (12) | 0.0612 (10) | 0.0080 (12) | −0.0148 (11) | 0.0118 (8) |
O37 | 0.153 (2) | 0.0750 (15) | 0.0736 (12) | 0.0185 (14) | 0.0626 (14) | 0.0073 (10) |
N37 | 0.0847 (11) | 0.0435 (8) | 0.0447 (8) | −0.0127 (7) | 0.0056 (7) | −0.0060 (6) |
O38 | 0.116 (10) | 0.076 (9) | 0.079 (9) | −0.015 (9) | 0.010 (9) | −0.003 (9) |
O39 | 0.095 (9) | 0.072 (9) | 0.051 (8) | 0.024 (8) | −0.021 (7) | 0.025 (8) |
N38 | 0.0847 (11) | 0.0435 (8) | 0.0447 (8) | −0.0127 (7) | 0.0056 (7) | −0.0060 (6) |
O310 | 0.119 (10) | 0.042 (7) | 0.056 (7) | −0.011 (8) | −0.004 (8) | −0.001 (6) |
O311 | 0.148 (10) | 0.055 (8) | 0.045 (7) | −0.019 (8) | 0.014 (8) | −0.015 (6) |
N1—C6 | 1.484 (2) | C25—C26 | 1.397 (2) |
N1—C2 | 1.4866 (19) | C25—H25 | 0.9300 |
N1—H11 | 0.869 (18) | C26—H26 | 0.9300 |
N1—H12 | 0.900 (19) | O22—C27 | 1.417 (2) |
C2—C3 | 1.506 (2) | C27—H27A | 0.9600 |
C2—H2A | 0.9700 | C27—H27B | 0.9600 |
C2—H2B | 0.9700 | C27—H27C | 0.9600 |
C3—N4 | 1.4661 (18) | C31—O31 | 1.2450 (15) |
C3—H3A | 0.9700 | C31—C32 | 1.4430 (18) |
C3—H3B | 0.9700 | C31—C36 | 1.4492 (19) |
N4—C21 | 1.4274 (17) | C32—C33 | 1.3749 (18) |
N4—C5 | 1.4601 (18) | C32—N32 | 1.4583 (17) |
C5—C6 | 1.508 (2) | N32—O32 | 1.2089 (16) |
C5—H5A | 0.9700 | N32—O33 | 1.2161 (16) |
C5—H5B | 0.9700 | C33—C34 | 1.3777 (19) |
C6—H6A | 0.9700 | C33—H33 | 0.9300 |
C6—H6B | 0.9700 | C34—C35 | 1.3892 (19) |
C21—C26 | 1.382 (2) | C34—N34 | 1.4454 (17) |
C21—C22 | 1.411 (2) | N34—O34 | 1.2260 (17) |
C22—O22 | 1.358 (2) | N34—O35 | 1.2326 (17) |
C22—C23 | 1.388 (2) | C35—C36 | 1.3623 (19) |
C23—C24 | 1.376 (3) | C35—H35 | 0.9300 |
C23—H23 | 0.9300 | C36—N36 | 1.4643 (19) |
C24—C25 | 1.367 (3) | N36—O36 | 1.199 (2) |
C24—H24 | 0.9300 | N36—O37 | 1.214 (2) |
C6—N1—C2 | 111.24 (11) | C25—C24—H24 | 119.8 |
C6—N1—H11 | 109.0 (11) | C23—C24—H24 | 119.8 |
C2—N1—H11 | 110.2 (11) | C24—C25—C26 | 120.14 (18) |
C6—N1—H12 | 109.4 (11) | C24—C25—H25 | 119.9 |
C2—N1—H12 | 108.7 (11) | C26—C25—H25 | 119.9 |
H11—N1—H12 | 108.3 (15) | C21—C26—C25 | 120.64 (18) |
N1—C2—C3 | 110.41 (12) | C21—C26—H26 | 119.7 |
N1—C2—H2A | 109.6 | C25—C26—H26 | 119.7 |
C3—C2—H2A | 109.6 | C22—O22—C27 | 119.05 (13) |
N1—C2—H2B | 109.6 | O22—C27—H27A | 109.5 |
C3—C2—H2B | 109.6 | O22—C27—H27B | 109.5 |
H2A—C2—H2B | 108.1 | H27A—C27—H27B | 109.5 |
N4—C3—C2 | 110.51 (13) | O22—C27—H27C | 109.5 |
N4—C3—H3A | 109.5 | H27A—C27—H27C | 109.5 |
C2—C3—H3A | 109.5 | H27B—C27—H27C | 109.5 |
N4—C3—H3B | 109.5 | O31—C31—C32 | 126.64 (12) |
C2—C3—H3B | 109.5 | O31—C31—C36 | 121.75 (12) |
H3A—C3—H3B | 108.1 | C32—C31—C36 | 111.56 (11) |
C21—N4—C5 | 115.52 (11) | C33—C32—C31 | 123.98 (12) |
C21—N4—C3 | 113.44 (11) | C33—C32—N32 | 116.28 (11) |
C5—N4—C3 | 109.59 (11) | C31—C32—N32 | 119.70 (11) |
N4—C5—C6 | 109.95 (12) | O32—N32—O33 | 122.28 (13) |
N4—C5—H5A | 109.7 | O32—N32—C32 | 119.94 (12) |
C6—C5—H5A | 109.7 | O33—N32—C32 | 117.78 (12) |
N4—C5—H5B | 109.7 | C32—C33—C34 | 119.57 (12) |
C6—C5—H5B | 109.7 | C32—C33—H33 | 120.2 |
H5A—C5—H5B | 108.2 | C34—C33—H33 | 120.2 |
N1—C6—C5 | 109.85 (12) | C33—C34—C35 | 121.15 (12) |
N1—C6—H6A | 109.7 | C33—C34—N34 | 119.23 (12) |
C5—C6—H6A | 109.7 | C35—C34—N34 | 119.56 (12) |
N1—C6—H6B | 109.7 | O34—N34—O35 | 122.70 (13) |
C5—C6—H6B | 109.7 | O34—N34—C34 | 118.86 (13) |
H6A—C6—H6B | 108.2 | O35—N34—C34 | 118.41 (13) |
C26—C21—C22 | 118.49 (13) | C36—C35—C34 | 118.47 (12) |
C26—C21—N4 | 122.91 (14) | C36—C35—H35 | 120.8 |
C22—C21—N4 | 118.58 (13) | C34—C35—H35 | 120.8 |
O22—C22—C23 | 123.92 (16) | C35—C36—C31 | 125.23 (12) |
O22—C22—C21 | 116.04 (12) | C35—C36—N36 | 117.48 (12) |
C23—C22—C21 | 120.03 (16) | C31—C36—N36 | 117.20 (12) |
C24—C23—C22 | 120.29 (18) | O36—N36—O37 | 124.53 (18) |
C24—C23—H23 | 119.9 | O36—N36—C36 | 118.10 (16) |
C22—C23—H23 | 119.9 | O37—N36—C36 | 117.11 (16) |
C25—C24—C23 | 120.37 (16) | ||
C6—N1—C2—C3 | 54.43 (18) | O31—C31—C32—N32 | −0.5 (2) |
N1—C2—C3—N4 | −56.58 (17) | C36—C31—C32—N32 | −177.72 (11) |
C2—C3—N4—C21 | −168.88 (12) | C33—C32—N32—O32 | 170.90 (15) |
C2—C3—N4—C5 | 60.37 (16) | C31—C32—N32—O32 | −11.3 (2) |
C21—N4—C5—C6 | 168.83 (12) | C33—C32—N32—O33 | −9.62 (19) |
C3—N4—C5—C6 | −61.53 (15) | C31—C32—N32—O33 | 168.23 (13) |
C2—N1—C6—C5 | −55.55 (16) | C31—C32—C33—C34 | 0.0 (2) |
N4—C5—C6—N1 | 59.07 (15) | N32—C32—C33—C34 | 177.78 (11) |
C5—N4—C21—C26 | 17.82 (19) | C32—C33—C34—C35 | −1.2 (2) |
C3—N4—C21—C26 | −109.92 (16) | C32—C33—C34—N34 | −178.48 (12) |
C5—N4—C21—C22 | −160.45 (13) | C33—C34—N34—O34 | −3.1 (2) |
C3—N4—C21—C22 | 71.82 (17) | C35—C34—N34—O34 | 179.59 (14) |
C26—C21—C22—O22 | −179.42 (14) | C33—C34—N34—O35 | 175.20 (13) |
N4—C21—C22—O22 | −1.1 (2) | C35—C34—N34—O35 | −2.1 (2) |
C26—C21—C22—C23 | −0.3 (2) | C33—C34—C35—C36 | 2.4 (2) |
N4—C21—C22—C23 | 178.00 (14) | N34—C34—C35—C36 | 179.67 (12) |
O22—C22—C23—C24 | 178.03 (17) | C34—C35—C36—C31 | −2.6 (2) |
C21—C22—C23—C24 | −1.0 (3) | C34—C35—C36—N36 | −179.06 (13) |
C22—C23—C24—C25 | 1.0 (3) | O31—C31—C36—C35 | −176.00 (13) |
C23—C24—C25—C26 | 0.4 (3) | C32—C31—C36—C35 | 1.36 (19) |
C22—C21—C26—C25 | 1.7 (2) | O31—C31—C36—N36 | 0.5 (2) |
N4—C21—C26—C25 | −176.60 (14) | C32—C31—C36—N36 | 177.86 (12) |
C24—C25—C26—C21 | −1.7 (3) | C35—C36—N36—O36 | 44.8 (3) |
C23—C22—O22—C27 | 13.9 (3) | C31—C36—N36—O36 | −132.0 (2) |
C21—C22—O22—C27 | −167.10 (17) | C35—C36—N36—O37 | −129.6 (3) |
O31—C31—C32—C33 | 177.16 (13) | C31—C36—N36—O37 | 53.7 (3) |
C36—C31—C32—C33 | −0.05 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H11···O33 | 0.868 (18) | 2.224 (18) | 2.9120 (19) | 136.1 (16) |
N1—H12···O31i | 0.900 (18) | 1.833 (18) | 2.7142 (18) | 165.9 (16) |
N1—H12···O32i | 0.900 (19) | 2.593 (17) | 3.154 (2) | 121.2 (13) |
C6—H6A···O34ii | 0.97 | 2.56 | 3.423 (2) | 148 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y+1, z. |
C11H17N2O+·C4H3O4− | Z = 4 |
Mr = 308.33 | F(000) = 656 |
Triclinic, P1 | Dx = 1.287 Mg m−3 |
a = 11.1076 (6) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.1164 (6) Å | Cell parameters from 6817 reflections |
c = 13.7649 (7) Å | θ = 2.6–27.9° |
α = 80.353 (5)° | µ = 0.10 mm−1 |
β = 78.353 (5)° | T = 296 K |
γ = 74.406 (5)° | Block, orange |
V = 1591.76 (16) Å3 | 0.48 × 0.40 × 0.36 mm |
Oxford Diffraction Xcalibur with Sapphire CCD diffractometer | 6817 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 4221 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.012 |
ω scans | θmax = 27.9°, θmin = 2.6° |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | h = −14→11 |
Tmin = 0.863, Tmax = 0.966 | k = −14→10 |
11727 measured reflections | l = −17→16 |
Refinement on F2 | Primary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.042 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.121 | w = 1/[σ2(Fo2) + (0.0662P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
6817 reflections | Δρmax = 0.15 e Å−3 |
415 parameters | Δρmin = −0.16 e Å−3 |
0 restraints |
Experimental. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. |
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 | ||
N11 | 0.34622 (12) | 0.18907 (13) | 0.37745 (11) | 0.0623 (4) | |
H111 | 0.2917 (16) | 0.2421 (16) | 0.4214 (12) | 0.075* | |
H112 | 0.3338 (15) | 0.1085 (16) | 0.3969 (11) | 0.075* | |
C12 | 0.47834 (15) | 0.19077 (16) | 0.38284 (12) | 0.0642 (4) | |
H12A | 0.4969 | 0.1564 | 0.4493 | 0.077* | |
H12B | 0.4870 | 0.2768 | 0.3702 | 0.077* | |
C13 | 0.57059 (14) | 0.11410 (15) | 0.30673 (11) | 0.0570 (4) | |
H13A | 0.6560 | 0.1195 | 0.3080 | 0.068* | |
H13B | 0.5675 | 0.0265 | 0.3231 | 0.068* | |
N14 | 0.53919 (10) | 0.16040 (11) | 0.20732 (8) | 0.0467 (3) | |
C15 | 0.41371 (12) | 0.14755 (14) | 0.20256 (12) | 0.0562 (4) | |
H15A | 0.4102 | 0.0602 | 0.2201 | 0.067* | |
H15B | 0.3954 | 0.1744 | 0.1352 | 0.067* | |
C16 | 0.31747 (14) | 0.22734 (15) | 0.27418 (13) | 0.0616 (4) | |
H16A | 0.3182 | 0.3151 | 0.2542 | 0.074* | |
H16B | 0.2335 | 0.2182 | 0.2724 | 0.074* | |
C121 | 0.63719 (12) | 0.12322 (13) | 0.12699 (10) | 0.0455 (3) | |
C122 | 0.74375 (13) | 0.17360 (14) | 0.10986 (11) | 0.0516 (4) | |
C123 | 0.83917 (14) | 0.14329 (16) | 0.02954 (12) | 0.0636 (4) | |
H123 | 0.9099 | 0.1764 | 0.0188 | 0.076* | |
C124 | 0.83016 (15) | 0.06460 (16) | −0.03458 (12) | 0.0669 (5) | |
H124 | 0.8946 | 0.0451 | −0.0884 | 0.080* | |
C125 | 0.72766 (15) | 0.01536 (16) | −0.01957 (12) | 0.0654 (4) | |
H125 | 0.7218 | −0.0375 | −0.0632 | 0.078* | |
C126 | 0.63143 (14) | 0.04385 (14) | 0.06097 (11) | 0.0576 (4) | |
H126 | 0.5618 | 0.0092 | 0.0709 | 0.069* | |
O122 | 0.74475 (10) | 0.25199 (11) | 0.17621 (8) | 0.0716 (3) | |
C127 | 0.84336 (17) | 0.31480 (17) | 0.15906 (15) | 0.0774 (5) | |
H17A | 0.8314 | 0.3660 | 0.2115 | 0.116* | |
H17B | 0.9234 | 0.2540 | 0.1580 | 0.116* | |
H17C | 0.8424 | 0.3671 | 0.0960 | 0.116* | |
N21 | 0.32610 (11) | 0.68791 (12) | 0.35465 (9) | 0.0506 (3) | |
H211 | 0.2716 (14) | 0.7345 (14) | 0.4078 (11) | 0.061* | |
H212 | 0.3068 (13) | 0.6135 (14) | 0.3614 (11) | 0.061* | |
C22 | 0.45843 (14) | 0.66671 (15) | 0.37162 (11) | 0.0559 (4) | |
H22A | 0.4692 | 0.6135 | 0.4343 | 0.067* | |
H22B | 0.4753 | 0.7466 | 0.3763 | 0.067* | |
C23 | 0.55121 (13) | 0.60521 (13) | 0.28769 (10) | 0.0510 (4) | |
H23A | 0.6371 | 0.5971 | 0.2979 | 0.061* | |
H23B | 0.5404 | 0.5216 | 0.2872 | 0.061* | |
N24 | 0.53089 (10) | 0.68033 (10) | 0.19212 (8) | 0.0443 (3) | |
C25 | 0.40353 (12) | 0.68965 (15) | 0.17454 (11) | 0.0548 (4) | |
H25A | 0.3914 | 0.6062 | 0.1757 | 0.066* | |
H25B | 0.3920 | 0.7357 | 0.1094 | 0.066* | |
C26 | 0.30813 (13) | 0.75658 (14) | 0.25435 (11) | 0.0549 (4) | |
H26A | 0.3179 | 0.8414 | 0.2509 | 0.066* | |
H26B | 0.2231 | 0.7622 | 0.2434 | 0.066* | |
C221 | 0.63168 (12) | 0.64911 (13) | 0.11180 (10) | 0.0454 (3) | |
C222 | 0.74589 (13) | 0.68107 (14) | 0.11058 (11) | 0.0505 (4) | |
C223 | 0.84489 (15) | 0.65473 (16) | 0.03183 (13) | 0.0660 (5) | |
H223 | 0.9205 | 0.6760 | 0.0311 | 0.079* | |
C224 | 0.83202 (17) | 0.59725 (17) | −0.04533 (13) | 0.0722 (5) | |
H224 | 0.8991 | 0.5797 | −0.0977 | 0.087* | |
C225 | 0.72259 (17) | 0.56616 (17) | −0.04537 (12) | 0.0735 (5) | |
H225 | 0.7143 | 0.5275 | −0.0977 | 0.088* | |
C226 | 0.62268 (16) | 0.59194 (16) | 0.03260 (11) | 0.0641 (4) | |
H226 | 0.5477 | 0.5703 | 0.0317 | 0.077* | |
O222 | 0.75012 (10) | 0.73834 (11) | 0.18954 (8) | 0.0683 (3) | |
C227 | 0.85515 (17) | 0.78893 (18) | 0.18703 (14) | 0.0806 (6) | |
H27A | 0.8449 | 0.8259 | 0.2473 | 0.121* | |
H27B | 0.9316 | 0.7230 | 0.1816 | 0.121* | |
H27C | 0.8601 | 0.8521 | 0.1305 | 0.121* | |
C31 | 0.21393 (13) | 0.42548 (13) | 0.52990 (11) | 0.0491 (3) | |
O31 | 0.31437 (10) | 0.44663 (10) | 0.48375 (9) | 0.0721 (3) | |
O32 | 0.17455 (10) | 0.33051 (9) | 0.52076 (8) | 0.0630 (3) | |
C32 | 0.13422 (14) | 0.51635 (13) | 0.59942 (11) | 0.0527 (4) | |
H32 | 0.1710 | 0.5799 | 0.6060 | 0.063* | |
C33 | 0.01974 (14) | 0.52237 (13) | 0.65358 (11) | 0.0515 (4) | |
H331 | −0.0094 | 0.5890 | 0.6919 | 0.062* | |
C34 | −0.06961 (14) | 0.44152 (13) | 0.66358 (11) | 0.0493 (4) | |
O33 | −0.03904 (10) | 0.34388 (9) | 0.61545 (8) | 0.0587 (3) | |
H33 | 0.0541 (18) | 0.3376 (15) | 0.5724 (13) | 0.088* | |
O34 | −0.17286 (11) | 0.46868 (11) | 0.71631 (9) | 0.0830 (4) | |
C41 | 0.21753 (13) | 0.92641 (13) | 0.50681 (10) | 0.0472 (3) | |
O41 | 0.31284 (10) | 0.95022 (9) | 0.45083 (8) | 0.0676 (3) | |
O42 | 0.18296 (10) | 0.82652 (9) | 0.50841 (8) | 0.0661 (3) | |
C42 | 0.14234 (14) | 1.02060 (13) | 0.57458 (11) | 0.0554 (4) | |
H42 | 0.1724 | 1.0926 | 0.5676 | 0.067* | |
C43 | 0.03981 (13) | 1.01999 (13) | 0.64339 (11) | 0.0536 (4) | |
H431 | 0.0104 | 1.0921 | 0.6756 | 0.064* | |
C44 | −0.03624 (14) | 0.92597 (13) | 0.67828 (11) | 0.0525 (4) | |
O43 | −0.01234 (11) | 0.82687 (10) | 0.63191 (9) | 0.0756 (4) | |
H43 | 0.066 (2) | 0.8219 (18) | 0.5806 (15) | 0.113* | |
O44 | −0.12061 (12) | 0.94251 (11) | 0.74866 (9) | 0.0869 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N11 | 0.0566 (8) | 0.0488 (8) | 0.0713 (10) | −0.0164 (6) | 0.0283 (7) | −0.0197 (7) |
C12 | 0.0610 (10) | 0.0759 (11) | 0.0497 (9) | −0.0144 (8) | 0.0086 (8) | −0.0156 (8) |
C13 | 0.0480 (9) | 0.0685 (10) | 0.0474 (9) | −0.0093 (7) | 0.0035 (7) | −0.0095 (7) |
N14 | 0.0351 (6) | 0.0597 (7) | 0.0451 (7) | −0.0136 (5) | 0.0027 (5) | −0.0138 (6) |
C15 | 0.0391 (8) | 0.0619 (9) | 0.0705 (10) | −0.0165 (7) | 0.0024 (7) | −0.0226 (8) |
C16 | 0.0389 (8) | 0.0622 (10) | 0.0817 (12) | −0.0128 (7) | 0.0077 (8) | −0.0233 (9) |
C121 | 0.0390 (7) | 0.0525 (8) | 0.0417 (8) | −0.0080 (6) | −0.0006 (6) | −0.0092 (6) |
C122 | 0.0445 (8) | 0.0603 (9) | 0.0483 (8) | −0.0159 (7) | 0.0038 (7) | −0.0111 (7) |
C123 | 0.0460 (9) | 0.0804 (11) | 0.0586 (10) | −0.0186 (8) | 0.0103 (7) | −0.0097 (9) |
C124 | 0.0546 (10) | 0.0855 (12) | 0.0474 (9) | −0.0003 (9) | 0.0066 (7) | −0.0172 (9) |
C125 | 0.0637 (11) | 0.0742 (11) | 0.0550 (10) | 0.0003 (8) | −0.0073 (8) | −0.0296 (8) |
C126 | 0.0500 (9) | 0.0654 (10) | 0.0600 (10) | −0.0121 (7) | −0.0065 (7) | −0.0211 (8) |
O122 | 0.0621 (7) | 0.0907 (8) | 0.0735 (8) | −0.0425 (6) | 0.0152 (6) | −0.0346 (7) |
C127 | 0.0680 (11) | 0.0796 (12) | 0.0960 (14) | −0.0367 (10) | −0.0123 (10) | −0.0126 (10) |
N21 | 0.0459 (7) | 0.0451 (7) | 0.0560 (8) | −0.0138 (6) | 0.0135 (6) | −0.0152 (6) |
C22 | 0.0519 (9) | 0.0666 (10) | 0.0432 (8) | −0.0120 (7) | 0.0029 (7) | −0.0064 (7) |
C23 | 0.0446 (8) | 0.0558 (9) | 0.0463 (8) | −0.0096 (7) | 0.0019 (6) | −0.0049 (7) |
N24 | 0.0362 (6) | 0.0554 (7) | 0.0402 (6) | −0.0131 (5) | 0.0009 (5) | −0.0085 (5) |
C25 | 0.0415 (8) | 0.0714 (10) | 0.0518 (9) | −0.0156 (7) | −0.0011 (7) | −0.0133 (7) |
C26 | 0.0394 (8) | 0.0578 (9) | 0.0632 (10) | −0.0095 (7) | 0.0004 (7) | −0.0103 (8) |
C221 | 0.0416 (8) | 0.0494 (8) | 0.0431 (8) | −0.0128 (6) | 0.0017 (6) | −0.0076 (6) |
C222 | 0.0456 (8) | 0.0556 (9) | 0.0497 (9) | −0.0182 (7) | 0.0020 (7) | −0.0063 (7) |
C223 | 0.0464 (9) | 0.0781 (11) | 0.0677 (11) | −0.0225 (8) | 0.0116 (8) | −0.0063 (9) |
C224 | 0.0671 (11) | 0.0813 (12) | 0.0551 (10) | −0.0155 (9) | 0.0207 (9) | −0.0132 (9) |
C225 | 0.0785 (12) | 0.0898 (13) | 0.0520 (10) | −0.0218 (10) | 0.0078 (9) | −0.0288 (9) |
C226 | 0.0621 (10) | 0.0839 (12) | 0.0530 (10) | −0.0279 (9) | 0.0021 (8) | −0.0242 (9) |
O222 | 0.0581 (7) | 0.0936 (8) | 0.0664 (7) | −0.0409 (6) | 0.0024 (5) | −0.0248 (6) |
C227 | 0.0703 (12) | 0.0969 (14) | 0.0911 (14) | −0.0433 (10) | −0.0245 (10) | −0.0056 (11) |
C31 | 0.0442 (8) | 0.0477 (8) | 0.0536 (9) | −0.0101 (6) | −0.0053 (7) | −0.0065 (7) |
O31 | 0.0473 (6) | 0.0693 (7) | 0.0955 (9) | −0.0180 (5) | 0.0097 (6) | −0.0181 (6) |
O32 | 0.0595 (7) | 0.0564 (6) | 0.0738 (7) | −0.0217 (5) | 0.0168 (5) | −0.0306 (5) |
C32 | 0.0555 (9) | 0.0422 (8) | 0.0653 (10) | −0.0176 (7) | −0.0070 (8) | −0.0143 (7) |
C33 | 0.0582 (9) | 0.0408 (8) | 0.0558 (9) | −0.0123 (7) | 0.0004 (7) | −0.0180 (7) |
C34 | 0.0545 (9) | 0.0416 (8) | 0.0479 (8) | −0.0125 (6) | 0.0058 (7) | −0.0107 (6) |
O33 | 0.0557 (6) | 0.0550 (6) | 0.0687 (7) | −0.0246 (5) | 0.0121 (5) | −0.0255 (5) |
O34 | 0.0722 (8) | 0.0720 (8) | 0.0981 (9) | −0.0285 (6) | 0.0364 (7) | −0.0352 (7) |
C41 | 0.0459 (8) | 0.0441 (8) | 0.0486 (8) | −0.0095 (6) | −0.0021 (7) | −0.0065 (6) |
O41 | 0.0577 (7) | 0.0555 (6) | 0.0801 (8) | −0.0158 (5) | 0.0177 (6) | −0.0139 (6) |
O42 | 0.0704 (7) | 0.0537 (6) | 0.0733 (7) | −0.0257 (5) | 0.0230 (6) | −0.0303 (5) |
C42 | 0.0574 (9) | 0.0424 (8) | 0.0688 (10) | −0.0190 (7) | 0.0029 (8) | −0.0180 (7) |
C43 | 0.0555 (9) | 0.0433 (8) | 0.0620 (9) | −0.0114 (7) | 0.0019 (7) | −0.0214 (7) |
C44 | 0.0541 (9) | 0.0486 (8) | 0.0521 (9) | −0.0119 (7) | 0.0051 (7) | −0.0161 (7) |
O43 | 0.0816 (8) | 0.0597 (7) | 0.0857 (9) | −0.0368 (6) | 0.0332 (7) | −0.0343 (6) |
O44 | 0.0886 (9) | 0.0869 (9) | 0.0816 (9) | −0.0369 (7) | 0.0373 (7) | −0.0372 (7) |
N11—C16 | 1.487 (2) | N24—C221 | 1.4199 (15) |
N11—C12 | 1.490 (2) | N24—C25 | 1.4566 (17) |
N11—H111 | 0.927 (17) | C25—C26 | 1.5045 (18) |
N11—H112 | 0.930 (16) | C25—H25A | 0.9700 |
C12—C13 | 1.5068 (19) | C25—H25B | 0.9700 |
C12—H12A | 0.9700 | C26—H26A | 0.9700 |
C12—H12B | 0.9700 | C26—H26B | 0.9700 |
C13—N14 | 1.4556 (18) | C221—C226 | 1.383 (2) |
C13—H13A | 0.9700 | C221—C222 | 1.4027 (18) |
C13—H13B | 0.9700 | C222—O222 | 1.3629 (17) |
N14—C121 | 1.4155 (16) | C222—C223 | 1.3863 (19) |
N14—C15 | 1.4541 (16) | C223—C224 | 1.376 (2) |
C15—C16 | 1.5031 (19) | C223—H223 | 0.9300 |
C15—H15A | 0.9700 | C224—C225 | 1.350 (2) |
C15—H15B | 0.9700 | C224—H224 | 0.9300 |
C16—H16A | 0.9700 | C225—C226 | 1.384 (2) |
C16—H16B | 0.9700 | C225—H225 | 0.9300 |
C121—C126 | 1.3896 (19) | C226—H226 | 0.9300 |
C121—C122 | 1.4034 (18) | O222—C227 | 1.4172 (17) |
C122—O122 | 1.3673 (17) | C227—H27A | 0.9600 |
C122—C123 | 1.3853 (19) | C227—H27B | 0.9600 |
C123—C124 | 1.377 (2) | C227—H27C | 0.9600 |
C123—H123 | 0.9300 | C31—O31 | 1.2281 (15) |
C124—C125 | 1.357 (2) | C31—O32 | 1.2793 (16) |
C124—H124 | 0.9300 | C31—C32 | 1.4904 (19) |
C125—C126 | 1.3889 (19) | C32—C33 | 1.3287 (18) |
C125—H125 | 0.9300 | C32—H32 | 0.9300 |
C126—H126 | 0.9300 | C33—C34 | 1.4814 (19) |
O122—C127 | 1.4123 (16) | C33—H331 | 0.9300 |
C127—H17A | 0.9600 | C34—O34 | 1.2185 (16) |
C127—H17B | 0.9600 | C34—O33 | 1.2977 (16) |
C127—H17C | 0.9600 | O33—H33 | 1.074 (19) |
N21—C22 | 1.4848 (19) | C41—O41 | 1.2400 (15) |
N21—C26 | 1.4849 (19) | C41—O42 | 1.2643 (15) |
N21—H211 | 0.974 (16) | C41—C42 | 1.4855 (19) |
N21—H212 | 0.894 (14) | C42—C43 | 1.3269 (18) |
C22—C23 | 1.5064 (18) | C42—H42 | 0.9300 |
C22—H22A | 0.9700 | C43—C44 | 1.4762 (19) |
C22—H22B | 0.9700 | C43—H431 | 0.9300 |
C23—N24 | 1.4592 (17) | C44—O44 | 1.2046 (16) |
C23—H23A | 0.9700 | C44—O43 | 1.3044 (16) |
C23—H23B | 0.9700 | O43—H43 | 1.00 (2) |
C16—N11—C12 | 111.87 (11) | C22—C23—H23A | 109.6 |
C16—N11—H111 | 111.2 (11) | N24—C23—H23B | 109.6 |
C12—N11—H111 | 107.9 (10) | C22—C23—H23B | 109.6 |
C16—N11—H112 | 106.9 (10) | H23A—C23—H23B | 108.1 |
C12—N11—H112 | 110.6 (10) | C221—N24—C25 | 116.82 (11) |
H111—N11—H112 | 108.4 (13) | C221—N24—C23 | 114.50 (11) |
N11—C12—C13 | 110.06 (13) | C25—N24—C23 | 110.09 (10) |
N11—C12—H12A | 109.6 | N24—C25—C26 | 109.32 (12) |
C13—C12—H12A | 109.6 | N24—C25—H25A | 109.8 |
N11—C12—H12B | 109.6 | C26—C25—H25A | 109.8 |
C13—C12—H12B | 109.6 | N24—C25—H25B | 109.8 |
H12A—C12—H12B | 108.2 | C26—C25—H25B | 109.8 |
N14—C13—C12 | 110.14 (12) | H25A—C25—H25B | 108.3 |
N14—C13—H13A | 109.6 | N21—C26—C25 | 110.30 (12) |
C12—C13—H13A | 109.6 | N21—C26—H26A | 109.6 |
N14—C13—H13B | 109.6 | C25—C26—H26A | 109.6 |
C12—C13—H13B | 109.6 | N21—C26—H26B | 109.6 |
H13A—C13—H13B | 108.1 | C25—C26—H26B | 109.6 |
C121—N14—C15 | 117.32 (11) | H26A—C26—H26B | 108.1 |
C121—N14—C13 | 115.49 (11) | C226—C221—C222 | 117.72 (12) |
C15—N14—C13 | 110.45 (11) | C226—C221—N24 | 123.68 (12) |
N14—C15—C16 | 108.98 (12) | C222—C221—N24 | 118.57 (12) |
N14—C15—H15A | 109.9 | O222—C222—C223 | 124.36 (13) |
C16—C15—H15A | 109.9 | O222—C222—C221 | 115.74 (12) |
N14—C15—H15B | 109.9 | C223—C222—C221 | 119.90 (14) |
C16—C15—H15B | 109.9 | C224—C223—C222 | 120.46 (14) |
H15A—C15—H15B | 108.3 | C224—C223—H223 | 119.8 |
N11—C16—C15 | 110.40 (13) | C222—C223—H223 | 119.8 |
N11—C16—H16A | 109.6 | C225—C224—C223 | 120.36 (14) |
C15—C16—H16A | 109.6 | C225—C224—H224 | 119.8 |
N11—C16—H16B | 109.6 | C223—C224—H224 | 119.8 |
C15—C16—H16B | 109.6 | C224—C225—C226 | 119.96 (15) |
H16A—C16—H16B | 108.1 | C224—C225—H225 | 120.0 |
C126—C121—C122 | 117.83 (12) | C226—C225—H225 | 120.0 |
C126—C121—N14 | 123.65 (12) | C221—C226—C225 | 121.60 (14) |
C122—C121—N14 | 118.45 (12) | C221—C226—H226 | 119.2 |
O122—C122—C123 | 124.19 (13) | C225—C226—H226 | 119.2 |
O122—C122—C121 | 115.76 (11) | C222—O222—C227 | 119.00 (12) |
C123—C122—C121 | 120.05 (14) | O222—C227—H27A | 109.5 |
C124—C123—C122 | 120.56 (14) | O222—C227—H27B | 109.5 |
C124—C123—H123 | 119.7 | H27A—C227—H27B | 109.5 |
C122—C123—H123 | 119.7 | O222—C227—H27C | 109.5 |
C125—C124—C123 | 120.29 (14) | H27A—C227—H27C | 109.5 |
C125—C124—H124 | 119.9 | H27B—C227—H27C | 109.5 |
C123—C124—H124 | 119.9 | O31—C31—O32 | 123.42 (13) |
C124—C125—C126 | 120.03 (14) | O31—C31—C32 | 117.74 (13) |
C124—C125—H125 | 120.0 | O32—C31—C32 | 118.84 (12) |
C126—C125—H125 | 120.0 | C31—O32—H33 | 111.0 (7) |
C125—C126—C121 | 121.23 (14) | C33—C32—C31 | 131.17 (13) |
C125—C126—H126 | 119.4 | C33—C32—H32 | 114.4 |
C121—C126—H126 | 119.4 | C31—C32—H32 | 114.4 |
C122—O122—C127 | 119.05 (12) | C32—C33—C34 | 131.27 (13) |
O122—C127—H17A | 109.5 | C32—C33—H331 | 114.4 |
O122—C127—H17B | 109.5 | C34—C33—H331 | 114.4 |
H17A—C127—H17B | 109.5 | O34—C34—O33 | 120.32 (13) |
O122—C127—H17C | 109.5 | O34—C34—C33 | 119.31 (13) |
H17A—C127—H17C | 109.5 | O33—C34—C33 | 120.37 (12) |
H17B—C127—H17C | 109.5 | C34—O33—H33 | 108.8 (9) |
C22—N21—C26 | 111.73 (11) | O41—C41—O42 | 122.92 (13) |
C22—N21—H211 | 106.8 (8) | O41—C41—C42 | 117.54 (12) |
C26—N21—H211 | 111.6 (9) | O42—C41—C42 | 119.54 (12) |
C22—N21—H212 | 108.9 (10) | C41—O42—H43 | 112.1 (8) |
C26—N21—H212 | 110.2 (10) | C43—C42—C41 | 131.25 (13) |
H211—N21—H212 | 107.5 (12) | C43—C42—H42 | 114.4 |
N21—C22—C23 | 110.82 (12) | C41—C42—H42 | 114.4 |
N21—C22—H22A | 109.5 | C42—C43—C44 | 131.86 (13) |
C23—C22—H22A | 109.5 | C42—C43—H431 | 114.1 |
N21—C22—H22B | 109.5 | C44—C43—H431 | 114.1 |
C23—C22—H22B | 109.5 | O44—C44—O43 | 120.81 (13) |
H22A—C22—H22B | 108.1 | O44—C44—C43 | 119.49 (13) |
N24—C23—C22 | 110.15 (12) | O43—C44—C43 | 119.69 (12) |
N24—C23—H23A | 109.6 | C44—O43—H43 | 111.0 (11) |
C16—N11—C12—C13 | −52.90 (17) | C23—N24—C25—C26 | 62.57 (15) |
N11—C12—C13—N14 | 56.09 (17) | C22—N21—C26—C25 | 54.13 (15) |
C12—C13—N14—C121 | 161.93 (12) | N24—C25—C26—N21 | −58.61 (15) |
C12—C13—N14—C15 | −61.98 (15) | C25—N24—C221—C226 | −20.0 (2) |
C121—N14—C15—C16 | −162.19 (12) | C23—N24—C221—C226 | 110.76 (16) |
C13—N14—C15—C16 | 62.61 (16) | C25—N24—C221—C222 | 157.98 (13) |
C12—N11—C16—C15 | 54.36 (16) | C23—N24—C221—C222 | −71.22 (16) |
N14—C15—C16—N11 | −58.23 (16) | C226—C221—C222—O222 | 179.36 (13) |
C15—N14—C121—C126 | −19.4 (2) | N24—C221—C222—O222 | 1.2 (2) |
C13—N14—C121—C126 | 113.61 (16) | C226—C221—C222—C223 | −0.2 (2) |
C15—N14—C121—C122 | 157.54 (13) | N24—C221—C222—C223 | −178.34 (13) |
C13—N14—C121—C122 | −69.47 (16) | O222—C222—C223—C224 | −179.56 (15) |
C126—C121—C122—O122 | 179.46 (13) | C221—C222—C223—C224 | 0.0 (2) |
N14—C121—C122—O122 | 2.4 (2) | C222—C223—C224—C225 | 0.2 (3) |
C126—C121—C122—C123 | −0.3 (2) | C223—C224—C225—C226 | −0.1 (3) |
N14—C121—C122—C123 | −177.42 (14) | C222—C221—C226—C225 | 0.3 (2) |
O122—C122—C123—C124 | −179.23 (15) | N24—C221—C226—C225 | 178.33 (15) |
C121—C122—C123—C124 | 0.5 (2) | C224—C225—C226—C221 | −0.2 (3) |
C122—C123—C124—C125 | −0.2 (3) | C223—C222—O222—C227 | 8.1 (2) |
C123—C124—C125—C126 | −0.2 (3) | C221—C222—O222—C227 | −171.41 (14) |
C124—C125—C126—C121 | 0.5 (2) | O31—C31—C32—C33 | 175.34 (16) |
C122—C121—C126—C125 | −0.2 (2) | O32—C31—C32—C33 | −4.3 (3) |
N14—C121—C126—C125 | 176.77 (14) | C31—C32—C33—C34 | −0.5 (3) |
C123—C122—O122—C127 | 5.1 (2) | C32—C33—C34—O34 | −177.55 (16) |
C121—C122—O122—C127 | −174.63 (14) | C32—C33—C34—O33 | 1.4 (3) |
C26—N21—C22—C23 | −52.60 (16) | O41—C41—C42—C43 | −177.97 (16) |
N21—C22—C23—N24 | 55.64 (15) | O42—C41—C42—C43 | 1.8 (3) |
C22—C23—N24—C221 | 164.83 (11) | C41—C42—C43—C44 | 0.5 (3) |
C22—C23—N24—C25 | −61.17 (14) | C42—C43—C44—O44 | 173.80 (18) |
C221—N24—C25—C26 | −164.61 (11) | C42—C43—C44—O43 | −7.0 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O33—H33···O32 | 1.07 (2) | 1.37 (2) | 2.4447 (16) | 177.7 (16) |
O43—H43···O42 | 1.00 (2) | 1.48 (2) | 2.4707 (17) | 174.0 (17) |
N11—H111···O32 | 0.927 (17) | 1.891 (17) | 2.8122 (18) | 172.3 (16) |
N11—H112···O41i | 0.930 (17) | 1.848 (17) | 2.7725 (17) | 172.9 (13) |
N21—H211···O42 | 0.975 (15) | 1.821 (15) | 2.7926 (16) | 174.5 (14) |
N21—H212···O31 | 0.895 (15) | 2.283 (15) | 2.9776 (17) | 134.4 (12) |
N21—H212···O34ii | 0.895 (15) | 2.428 (15) | 3.1170 (18) | 134.1 (12) |
C16—H16A···O34ii | 0.97 | 2.55 | 3.341 (2) | 138 |
C16—H16B···O44ii | 0.97 | 2.52 | 3.338 (2) | 141 |
C25—H25B···Cg4iii | 0.97 | 2.92 | 3.8440 (16) | 159 |
Symmetry codes: (i) x, y−1, z; (ii) −x, −y+1, −z+1; (iii) −x+1, −y, −z. |
C11H17N2O+·C4H3O4− | Z = 2 |
Mr = 308.33 | F(000) = 328 |
Triclinic, P1 | Dx = 1.326 Mg m−3 |
a = 7.8546 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.9626 (6) Å | Cell parameters from 3307 reflections |
c = 11.2056 (8) Å | θ = 2.6–27.8° |
α = 79.043 (5)° | µ = 0.10 mm−1 |
β = 87.715 (5)° | T = 296 K |
γ = 85.840 (5)° | Block, colourless |
V = 772.15 (9) Å3 | 0.48 × 0.48 × 0.34 mm |
Oxford Diffraction Xcalibur with Sapphire CCD diffractometer | 3307 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 2608 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.009 |
ω scans | θmax = 27.8°, θmin = 2.6° |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | h = −10→5 |
Tmin = 0.867, Tmax = 0.967 | k = −11→11 |
5533 measured reflections | l = −13→14 |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.036 | w = 1/[σ2(Fo2) + (0.0552P)2 + 0.0881P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.105 | (Δ/σ)max < 0.001 |
S = 1.06 | Δρmax = 0.20 e Å−3 |
3307 reflections | Δρmin = −0.15 e Å−3 |
240 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
6 restraints | Extinction coefficient: 0.022 (4) |
Primary atom site location: difference Fourier map |
Experimental. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. |
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) | |
N1 | 0.47840 (14) | 0.33032 (13) | 0.75754 (9) | 0.0496 (3) | |
H11 | 0.5555 | 0.3715 | 0.7951 | 0.059* | |
H12 | 0.4236 | 0.2650 | 0.8131 | 0.059* | |
C2 | 0.56542 (16) | 0.24842 (16) | 0.66646 (12) | 0.0521 (3) | |
H2A | 0.6417 | 0.1661 | 0.7071 | 0.063* | |
H2B | 0.6330 | 0.3178 | 0.6099 | 0.063* | |
C3 | 0.43454 (16) | 0.18491 (14) | 0.59804 (12) | 0.0478 (3) | |
H3A | 0.4922 | 0.1350 | 0.5367 | 0.057* | |
H3B | 0.3740 | 0.1092 | 0.6540 | 0.057* | |
N4 | 0.31104 (13) | 0.30552 (11) | 0.53920 (9) | 0.0435 (2) | |
C5 | 0.22526 (17) | 0.38282 (15) | 0.63102 (12) | 0.0499 (3) | |
H5A | 0.1632 | 0.3105 | 0.6890 | 0.060* | |
H5B | 0.1438 | 0.4621 | 0.5923 | 0.060* | |
C6 | 0.35447 (19) | 0.45212 (16) | 0.69650 (13) | 0.0561 (3) | |
H6A | 0.4148 | 0.5262 | 0.6389 | 0.067* | |
H6B | 0.2966 | 0.5042 | 0.7565 | 0.067* | |
C21 | 0.19938 (15) | 0.25100 (13) | 0.46154 (11) | 0.0427 (3) | |
C22 | 0.26637 (16) | 0.21262 (14) | 0.35255 (11) | 0.0463 (3) | |
C23 | 0.16107 (18) | 0.15988 (17) | 0.27531 (13) | 0.0576 (3) | |
H23 | 0.2063 | 0.1337 | 0.2035 | 0.069* | |
C24 | −0.01099 (19) | 0.14591 (19) | 0.30429 (15) | 0.0649 (4) | |
H24 | −0.0806 | 0.1102 | 0.2521 | 0.078* | |
C25 | −0.07834 (18) | 0.18457 (18) | 0.40935 (15) | 0.0644 (4) | |
H25 | −0.1940 | 0.1763 | 0.4283 | 0.077* | |
C26 | 0.02619 (17) | 0.23620 (15) | 0.48775 (13) | 0.0532 (3) | |
H26 | −0.0207 | 0.2615 | 0.5594 | 0.064* | |
O22 | 0.43698 (12) | 0.23087 (12) | 0.32891 (8) | 0.0587 (3) | |
C27 | 0.50598 (18) | 0.20342 (16) | 0.21566 (12) | 0.0541 (3) | |
H27A | 0.6256 | 0.2200 | 0.2105 | 0.081* | |
H27B | 0.4904 | 0.1001 | 0.2090 | 0.081* | |
H27C | 0.4486 | 0.2715 | 0.1508 | 0.081* | |
C31 | 0.7592 (6) | 0.4912 (5) | 0.9702 (5) | 0.0396 (11) | 0.572 (9) |
O31 | 0.7521 (6) | 0.4322 (5) | 0.8811 (5) | 0.0587 (10) | 0.572 (9) |
O32 | 0.6295 (6) | 0.5334 (6) | 1.0339 (5) | 0.0540 (9) | 0.572 (9) |
H32 | 0.5412 | 0.5112 | 1.0068 | 0.081* | 0.286 |
C32 | 0.9263 (5) | 0.5248 (3) | 1.0179 (3) | 0.0476 (11) | 0.572 (9) |
H32A | 0.9320 | 0.6190 | 1.0756 | 0.057* | 0.572 (9) |
C34 | 0.7860 (7) | 0.4556 (8) | 0.9314 (7) | 0.0410 (14) | 0.428 (9) |
O33 | 0.7520 (8) | 0.4140 (9) | 0.8394 (6) | 0.0583 (12) | 0.428 (9) |
O34 | 0.6784 (8) | 0.4985 (9) | 1.0107 (5) | 0.0557 (14) | 0.428 (9) |
H34 | 0.5809 | 0.4886 | 0.9913 | 0.084* | 0.214 |
C33 | 0.9707 (5) | 0.4644 (5) | 0.9604 (4) | 0.0472 (15) | 0.428 (9) |
H33A | 1.0572 | 0.4552 | 0.8986 | 0.057* | 0.428 (9) |
C41 | 0.24159 (13) | 0.01915 (13) | 0.97848 (10) | 0.0383 (3) | |
O41 | 0.25523 (10) | 0.12259 (12) | 0.89098 (9) | 0.0615 (3) | |
O42 | 0.36567 (10) | −0.05149 (12) | 1.04016 (8) | 0.0574 (3) | |
H42 | 0.4557 | −0.0178 | 1.0112 | 0.086* | 0.5 |
C42 | 0.07112 (13) | −0.03520 (14) | 1.02179 (10) | 0.0393 (3) | |
H42A | 0.0657 | −0.1221 | 1.0818 | 0.047* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0464 (6) | 0.0605 (7) | 0.0424 (5) | −0.0165 (5) | −0.0024 (4) | −0.0058 (5) |
C2 | 0.0406 (7) | 0.0675 (8) | 0.0470 (7) | −0.0047 (6) | −0.0008 (5) | −0.0071 (6) |
C3 | 0.0443 (7) | 0.0494 (7) | 0.0489 (7) | 0.0028 (5) | −0.0057 (5) | −0.0081 (5) |
N4 | 0.0452 (6) | 0.0427 (5) | 0.0427 (5) | −0.0007 (4) | −0.0064 (4) | −0.0076 (4) |
C5 | 0.0524 (7) | 0.0463 (7) | 0.0513 (7) | 0.0047 (5) | −0.0088 (6) | −0.0114 (5) |
C6 | 0.0666 (9) | 0.0500 (7) | 0.0535 (8) | −0.0074 (6) | −0.0068 (6) | −0.0121 (6) |
C21 | 0.0432 (6) | 0.0374 (6) | 0.0463 (6) | −0.0015 (5) | −0.0077 (5) | −0.0043 (5) |
C22 | 0.0416 (6) | 0.0481 (7) | 0.0496 (7) | −0.0042 (5) | −0.0059 (5) | −0.0088 (5) |
C23 | 0.0527 (8) | 0.0692 (9) | 0.0557 (8) | −0.0046 (6) | −0.0071 (6) | −0.0227 (7) |
C24 | 0.0501 (8) | 0.0785 (10) | 0.0735 (10) | −0.0069 (7) | −0.0142 (7) | −0.0292 (8) |
C25 | 0.0400 (7) | 0.0780 (10) | 0.0783 (10) | −0.0063 (7) | −0.0053 (7) | −0.0211 (8) |
C26 | 0.0451 (7) | 0.0573 (8) | 0.0582 (8) | −0.0007 (6) | −0.0026 (6) | −0.0142 (6) |
O22 | 0.0458 (5) | 0.0834 (7) | 0.0526 (5) | −0.0150 (5) | 0.0024 (4) | −0.0235 (5) |
C27 | 0.0530 (8) | 0.0604 (8) | 0.0467 (7) | −0.0043 (6) | 0.0009 (6) | −0.0050 (6) |
C31 | 0.035 (2) | 0.0441 (19) | 0.040 (3) | −0.0097 (16) | −0.0107 (19) | −0.0044 (15) |
O31 | 0.0420 (13) | 0.0858 (19) | 0.060 (3) | −0.0113 (11) | −0.0172 (19) | −0.038 (2) |
O32 | 0.0362 (19) | 0.081 (2) | 0.0480 (18) | −0.0149 (14) | −0.0069 (14) | −0.0143 (13) |
C32 | 0.037 (2) | 0.0607 (15) | 0.0489 (17) | −0.0106 (11) | −0.0115 (12) | −0.0157 (12) |
C34 | 0.033 (2) | 0.053 (3) | 0.039 (4) | −0.0108 (19) | −0.008 (2) | −0.011 (2) |
O33 | 0.0441 (15) | 0.086 (3) | 0.054 (3) | −0.0188 (15) | −0.015 (2) | −0.028 (2) |
O34 | 0.039 (4) | 0.089 (4) | 0.044 (3) | −0.017 (3) | −0.010 (2) | −0.0188 (19) |
C33 | 0.033 (2) | 0.068 (2) | 0.044 (2) | −0.0125 (15) | −0.0099 (15) | −0.0141 (18) |
C41 | 0.0237 (5) | 0.0535 (7) | 0.0386 (6) | −0.0081 (4) | 0.0017 (4) | −0.0091 (5) |
O41 | 0.0273 (4) | 0.0793 (7) | 0.0671 (6) | −0.0118 (4) | −0.0007 (4) | 0.0162 (5) |
O42 | 0.0222 (4) | 0.0826 (7) | 0.0590 (6) | −0.0101 (4) | −0.0031 (4) | 0.0110 (5) |
C42 | 0.0254 (5) | 0.0516 (6) | 0.0407 (6) | −0.0093 (4) | 0.0010 (4) | −0.0058 (5) |
N1—C2 | 1.4845 (17) | C24—H24 | 0.9300 |
N1—C6 | 1.4907 (17) | C25—C26 | 1.3883 (19) |
N1—H11 | 0.8900 | C25—H25 | 0.9300 |
N1—H12 | 0.8900 | C26—H26 | 0.9300 |
C2—C3 | 1.5108 (18) | O22—C27 | 1.4175 (16) |
C2—H2A | 0.9700 | C27—H27A | 0.9600 |
C2—H2B | 0.9700 | C27—H27B | 0.9600 |
C3—N4 | 1.4738 (15) | C27—H27C | 0.9600 |
C3—H3A | 0.9700 | C31—O31 | 1.221 (4) |
C3—H3B | 0.9700 | C31—O32 | 1.296 (5) |
N4—C21 | 1.4318 (15) | C31—C32 | 1.508 (4) |
N4—C5 | 1.4630 (16) | O32—H32 | 0.8200 |
C5—C6 | 1.5093 (18) | C32—H32A | 1.1605 |
C5—H5A | 0.9700 | C34—O33 | 1.207 (6) |
C5—H5B | 0.9700 | C34—O34 | 1.294 (6) |
C6—H6A | 0.9700 | C34—C33 | 1.510 (5) |
C6—H6B | 0.9700 | O34—H34 | 0.8200 |
C21—C26 | 1.3906 (18) | C33—H33A | 0.9611 |
C21—C22 | 1.4033 (18) | C41—O41 | 1.2219 (14) |
C22—O22 | 1.3710 (16) | C41—O42 | 1.2752 (14) |
C22—C23 | 1.3877 (18) | C41—C42 | 1.4895 (14) |
C23—C24 | 1.386 (2) | O42—H42 | 0.8200 |
C23—H23 | 0.9300 | C42—C42i | 1.307 (2) |
C24—C25 | 1.365 (2) | C42—H42A | 0.9300 |
C2—N1—C6 | 110.03 (10) | C23—C22—C21 | 120.06 (12) |
C2—N1—H11 | 109.7 | C24—C23—C22 | 120.53 (13) |
C6—N1—H11 | 109.7 | C24—C23—H23 | 119.7 |
C2—N1—H12 | 109.7 | C22—C23—H23 | 119.7 |
C6—N1—H12 | 109.7 | C25—C24—C23 | 120.04 (13) |
H11—N1—H12 | 108.2 | C25—C24—H24 | 120.0 |
N1—C2—C3 | 109.88 (10) | C23—C24—H24 | 120.0 |
N1—C2—H2A | 109.7 | C24—C25—C26 | 119.89 (13) |
C3—C2—H2A | 109.7 | C24—C25—H25 | 120.1 |
N1—C2—H2B | 109.7 | C26—C25—H25 | 120.1 |
C3—C2—H2B | 109.7 | C25—C26—C21 | 121.48 (13) |
H2A—C2—H2B | 108.2 | C25—C26—H26 | 119.3 |
N4—C3—C2 | 111.53 (10) | C21—C26—H26 | 119.3 |
N4—C3—H3A | 109.3 | C22—O22—C27 | 117.72 (10) |
C2—C3—H3A | 109.3 | O22—C27—H27A | 109.5 |
N4—C3—H3B | 109.3 | O22—C27—H27B | 109.5 |
C2—C3—H3B | 109.3 | H27A—C27—H27B | 109.5 |
H3A—C3—H3B | 108.0 | O22—C27—H27C | 109.5 |
C21—N4—C5 | 115.02 (10) | H27A—C27—H27C | 109.5 |
C21—N4—C3 | 112.31 (9) | H27B—C27—H27C | 109.5 |
C5—N4—C3 | 109.65 (9) | O31—C31—O32 | 125.7 (4) |
N4—C5—C6 | 110.19 (11) | O31—C31—C32 | 122.3 (5) |
N4—C5—H5A | 109.6 | O32—C31—C32 | 112.0 (5) |
C6—C5—H5A | 109.6 | C31—O32—H32 | 109.5 |
N4—C5—H5B | 109.6 | C31—C32—H32A | 120.8 |
C6—C5—H5B | 109.6 | O33—C34—O34 | 126.6 (6) |
H5A—C5—H5B | 108.1 | O33—C34—C33 | 119.4 (6) |
N1—C6—C5 | 109.74 (11) | O34—C34—C33 | 114.0 (5) |
N1—C6—H6A | 109.7 | C34—O34—H34 | 109.5 |
C5—C6—H6A | 109.7 | C34—C33—H33A | 119.0 |
N1—C6—H6B | 109.7 | O41—C41—O42 | 125.06 (10) |
C5—C6—H6B | 109.7 | O41—C41—C42 | 120.88 (10) |
H6A—C6—H6B | 108.2 | O42—C41—C42 | 114.07 (10) |
C26—C21—C22 | 118.00 (11) | C41—O42—H42 | 109.5 |
C26—C21—N4 | 123.21 (11) | C42i—C42—C41 | 122.20 (14) |
C22—C21—N4 | 118.79 (11) | C42i—C42—H42A | 118.9 |
O22—C22—C23 | 123.60 (12) | C41—C42—H42A | 118.9 |
O22—C22—C21 | 116.34 (10) | ||
C6—N1—C2—C3 | −56.53 (14) | C26—C21—C22—C23 | −0.80 (19) |
N1—C2—C3—N4 | 56.82 (14) | N4—C21—C22—C23 | −179.82 (11) |
C2—C3—N4—C21 | 172.63 (10) | O22—C22—C23—C24 | −179.23 (14) |
C2—C3—N4—C5 | −58.17 (13) | C21—C22—C23—C24 | 0.6 (2) |
C21—N4—C5—C6 | −172.92 (10) | C22—C23—C24—C25 | 0.2 (2) |
C3—N4—C5—C6 | 59.39 (13) | C23—C24—C25—C26 | −0.7 (2) |
C2—N1—C6—C5 | 58.42 (14) | C24—C25—C26—C21 | 0.5 (2) |
N4—C5—C6—N1 | −60.04 (14) | C22—C21—C26—C25 | 0.3 (2) |
C5—N4—C21—C26 | −15.65 (17) | N4—C21—C26—C25 | 179.22 (12) |
C3—N4—C21—C26 | 110.69 (13) | C23—C22—O22—C27 | 4.19 (19) |
C5—N4—C21—C22 | 163.31 (11) | C21—C22—O22—C27 | −175.63 (11) |
C3—N4—C21—C22 | −70.35 (14) | O41—C41—C42—C42i | −8.0 (2) |
C26—C21—C22—O22 | 179.03 (11) | O42—C41—C42—C42i | 172.10 (15) |
N4—C21—C22—O22 | 0.02 (17) |
Symmetry code: (i) −x, −y, −z+2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H11···O31 | 0.89 | 2.01 | 2.894 (5) | 171 |
N1—H11···O33 | 0.89 | 1.73 | 2.584 (7) | 160 |
N1—H12···O41 | 0.89 | 1.97 | 2.8251 (15) | 161 |
O32—H32···O32ii | 0.82 | 1.54 | 2.355 (7) | 176 |
O34—H34···O34ii | 0.82 | 2.03 | 2.820 (9) | 161 |
O42—H42···O42iii | 0.82 | 1.62 | 2.4352 (12) | 177 |
Symmetry codes: (ii) −x+1, −y+1, −z+2; (iii) −x+1, −y, −z+2. |
C11H17N2O+·C4H5O6−·1.698H2O | F(000) = 398 |
Mr = 372.97 | Dx = 1.345 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.479 (1) Å | Cell parameters from 2896 reflections |
b = 7.065 (1) Å | θ = 3.1–27.9° |
c = 17.788 (3) Å | µ = 0.11 mm−1 |
β = 101.58 (2)° | T = 296 K |
V = 920.8 (2) Å3 | Plate, colourless |
Z = 2 | 0.36 × 0.32 × 0.12 mm |
Oxford Diffraction Xcalibur with Sapphire CCD diffractometer | 2895 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 2062 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
ω scans | θmax = 27.9°, θmin = 3.1° |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | h = −9→9 |
Tmin = 0.956, Tmax = 0.987 | k = −9→6 |
3655 measured reflections | l = −23→22 |
Refinement on F2 | Primary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.039 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.081 | w = 1/[σ2(Fo2) + (0.0402P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.97 | (Δ/σ)max < 0.001 |
2895 reflections | Δρmax = 0.14 e Å−3 |
263 parameters | Δρmin = −0.17 e Å−3 |
4 restraints | Absolute structure: Flack x determined using 493 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
Experimental. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. |
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) | |
N1 | 0.4545 (5) | 0.3626 (4) | 0.31605 (16) | 0.0472 (7) | |
H11 | 0.517 (5) | 0.295 (5) | 0.3458 (19) | 0.057* | |
H12 | 0.341 (5) | 0.371 (6) | 0.3245 (18) | 0.057* | |
C2 | 0.4519 (5) | 0.2806 (5) | 0.23968 (19) | 0.0514 (9) | |
H2A | 0.3910 | 0.1588 | 0.2356 | 0.062* | |
H2B | 0.5760 | 0.2611 | 0.2328 | 0.062* | |
C3 | 0.3538 (5) | 0.4111 (4) | 0.17851 (18) | 0.0454 (8) | |
H3A | 0.3539 | 0.3575 | 0.1283 | 0.055* | |
H3B | 0.2280 | 0.4258 | 0.1839 | 0.055* | |
N4 | 0.4437 (3) | 0.5952 (4) | 0.18516 (13) | 0.0393 (6) | |
C5 | 0.4369 (5) | 0.6791 (5) | 0.25945 (16) | 0.0441 (8) | |
H5A | 0.3106 | 0.6953 | 0.2639 | 0.053* | |
H5B | 0.4941 | 0.8029 | 0.2633 | 0.053* | |
C6 | 0.5333 (5) | 0.5553 (4) | 0.32330 (19) | 0.0521 (10) | |
H6A | 0.6621 | 0.5488 | 0.3217 | 0.063* | |
H6B | 0.5219 | 0.6093 | 0.3723 | 0.063* | |
C21 | 0.3879 (5) | 0.7242 (5) | 0.12346 (16) | 0.0416 (8) | |
C22 | 0.5099 (5) | 0.8649 (5) | 0.11148 (18) | 0.0515 (9) | |
C23 | 0.4638 (6) | 0.9900 (6) | 0.0511 (2) | 0.0665 (11) | |
H23 | 0.5453 | 1.0842 | 0.0435 | 0.080* | |
C24 | 0.2984 (7) | 0.9750 (7) | 0.0025 (2) | 0.0749 (13) | |
H24 | 0.2678 | 1.0590 | −0.0383 | 0.090* | |
C25 | 0.1785 (6) | 0.8393 (7) | 0.0131 (2) | 0.0695 (12) | |
H25 | 0.0662 | 0.8300 | −0.0205 | 0.083* | |
C26 | 0.2227 (5) | 0.7140 (6) | 0.07395 (18) | 0.0546 (9) | |
H26 | 0.1390 | 0.6219 | 0.0812 | 0.066* | |
O22 | 0.6727 (4) | 0.8666 (4) | 0.16178 (15) | 0.0723 (8) | |
C27 | 0.8158 (6) | 0.9858 (8) | 0.1471 (3) | 0.0936 (15) | |
H27A | 0.9212 | 0.9712 | 0.1875 | 0.140* | |
H27B | 0.8463 | 0.9511 | 0.0990 | 0.140* | |
H27C | 0.7762 | 1.1153 | 0.1449 | 0.140* | |
C31 | 0.8601 (4) | 0.0130 (4) | 0.38558 (16) | 0.0321 (7) | |
O31 | 0.8264 (3) | 0.1842 (3) | 0.36938 (12) | 0.0422 (5) | |
O32 | 0.7484 (3) | −0.1056 (3) | 0.39964 (13) | 0.0484 (6) | |
C32 | 1.0532 (4) | −0.0580 (4) | 0.38922 (16) | 0.0300 (7) | |
H32A | 1.0927 | −0.0187 | 0.3423 | 0.036* | |
O33 | 1.0645 (3) | −0.2564 (3) | 0.39473 (13) | 0.0431 (6) | |
H33 | 0.985 (5) | −0.285 (6) | 0.414 (2) | 0.065* | |
C33 | 1.1809 (3) | 0.0309 (4) | 0.45784 (14) | 0.0292 (7) | |
H33A | 1.1800 | 0.1684 | 0.4506 | 0.035* | |
O34 | 1.1191 (3) | −0.0087 (3) | 0.52580 (11) | 0.0405 (5) | |
H34 | 1.162 (5) | −0.109 (6) | 0.544 (2) | 0.061* | |
C34 | 1.3725 (4) | −0.0400 (4) | 0.46138 (16) | 0.0307 (7) | |
O35 | 1.4553 (3) | −0.1271 (3) | 0.51524 (11) | 0.0479 (6) | |
O36 | 1.4319 (3) | −0.0004 (3) | 0.39858 (11) | 0.0351 (5) | |
H36 | 1.537 (5) | −0.036 (6) | 0.4062 (17) | 0.053* | |
O41 | 0.0854 (4) | 0.4055 (4) | 0.31999 (16) | 0.0612 (8) | |
H41 | 0.068 (6) | 0.512 (7) | 0.336 (2) | 0.092* | |
H42 | −0.004 (6) | 0.335 (7) | 0.329 (2) | 0.092* | |
O51 | −0.1304 (7) | 0.4856 (9) | 0.1775 (2) | 0.104 (2) | 0.698 (9) |
H51 | −0.051 (9) | 0.470 (13) | 0.228 (2) | 0.157* | 0.698 (9) |
H52 | −0.225 (8) | 0.573 (10) | 0.185 (4) | 0.157* | 0.698 (9) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0576 (19) | 0.0355 (16) | 0.0460 (17) | −0.0002 (16) | 0.0043 (15) | 0.0093 (14) |
C2 | 0.063 (2) | 0.0322 (18) | 0.061 (2) | 0.0033 (17) | 0.0179 (18) | 0.0013 (16) |
C3 | 0.057 (2) | 0.0362 (19) | 0.0443 (18) | −0.0014 (17) | 0.0143 (15) | −0.0036 (14) |
N4 | 0.0462 (16) | 0.0352 (14) | 0.0382 (14) | 0.0025 (13) | 0.0127 (12) | 0.0025 (12) |
C5 | 0.060 (2) | 0.0325 (17) | 0.0389 (17) | −0.0028 (17) | 0.0080 (16) | 0.0031 (15) |
C6 | 0.065 (2) | 0.040 (2) | 0.0468 (18) | −0.0102 (18) | −0.0007 (17) | 0.0083 (15) |
C21 | 0.053 (2) | 0.0404 (19) | 0.0355 (16) | 0.0091 (16) | 0.0186 (15) | 0.0017 (15) |
C22 | 0.064 (2) | 0.047 (2) | 0.0475 (19) | 0.002 (2) | 0.0208 (17) | 0.0074 (18) |
C23 | 0.093 (3) | 0.054 (2) | 0.062 (2) | 0.005 (2) | 0.037 (2) | 0.015 (2) |
C24 | 0.104 (4) | 0.067 (3) | 0.058 (2) | 0.024 (3) | 0.026 (2) | 0.026 (2) |
C25 | 0.074 (3) | 0.077 (3) | 0.053 (2) | 0.018 (3) | 0.003 (2) | 0.009 (2) |
C26 | 0.056 (2) | 0.057 (2) | 0.0502 (19) | 0.009 (2) | 0.0081 (17) | 0.0031 (19) |
O22 | 0.0621 (16) | 0.0759 (19) | 0.0786 (17) | −0.0177 (16) | 0.0137 (14) | 0.0213 (16) |
C27 | 0.078 (3) | 0.091 (3) | 0.118 (4) | −0.030 (3) | 0.034 (3) | 0.010 (3) |
C31 | 0.0235 (14) | 0.0325 (18) | 0.0411 (15) | 0.0001 (14) | 0.0084 (12) | −0.0038 (14) |
O31 | 0.0316 (11) | 0.0350 (13) | 0.0616 (13) | 0.0062 (10) | 0.0129 (10) | 0.0057 (11) |
O32 | 0.0248 (10) | 0.0384 (13) | 0.0869 (16) | −0.0026 (10) | 0.0224 (10) | 0.0027 (12) |
C32 | 0.0268 (15) | 0.0240 (15) | 0.0419 (15) | 0.0009 (12) | 0.0130 (12) | −0.0027 (13) |
O33 | 0.0312 (12) | 0.0296 (12) | 0.0749 (16) | −0.0031 (10) | 0.0256 (11) | −0.0055 (11) |
C33 | 0.0243 (14) | 0.0284 (16) | 0.0364 (15) | 0.0027 (12) | 0.0098 (12) | 0.0044 (13) |
O34 | 0.0407 (12) | 0.0439 (14) | 0.0424 (11) | 0.0089 (11) | 0.0212 (10) | 0.0037 (11) |
C34 | 0.0244 (14) | 0.0311 (15) | 0.0368 (15) | −0.0018 (13) | 0.0063 (13) | −0.0025 (14) |
O35 | 0.0388 (12) | 0.0597 (15) | 0.0442 (12) | 0.0126 (12) | 0.0058 (10) | 0.0128 (12) |
O36 | 0.0200 (9) | 0.0436 (13) | 0.0435 (11) | 0.0026 (10) | 0.0104 (9) | 0.0042 (10) |
O41 | 0.0671 (17) | 0.0429 (16) | 0.0847 (18) | −0.0022 (14) | 0.0415 (14) | −0.0044 (13) |
O51 | 0.104 (4) | 0.137 (5) | 0.072 (3) | 0.042 (4) | 0.020 (2) | 0.004 (3) |
N1—C2 | 1.473 (4) | C25—C26 | 1.386 (5) |
N1—C6 | 1.479 (4) | C25—H25 | 0.9300 |
N1—H11 | 0.79 (4) | C26—H26 | 0.9300 |
N1—H12 | 0.90 (4) | O22—C27 | 1.427 (5) |
C2—C3 | 1.500 (4) | C27—H27A | 0.9600 |
C2—H2A | 0.9700 | C27—H27B | 0.9600 |
C2—H2B | 0.9700 | C27—H27C | 0.9600 |
C3—N4 | 1.458 (4) | C31—O32 | 1.244 (4) |
C3—H3A | 0.9700 | C31—O31 | 1.257 (4) |
C3—H3B | 0.9700 | C31—C32 | 1.518 (4) |
N4—C21 | 1.423 (4) | C32—O33 | 1.406 (3) |
N4—C5 | 1.458 (4) | C32—C33 | 1.526 (4) |
C5—C6 | 1.499 (4) | C32—H32A | 0.9800 |
C5—H5A | 0.9700 | O33—H33 | 0.78 (4) |
C5—H5B | 0.9700 | C33—O34 | 1.406 (3) |
C6—H6A | 0.9700 | C33—C34 | 1.508 (4) |
C6—H6B | 0.9700 | C33—H33A | 0.9800 |
C21—C26 | 1.368 (4) | O34—H34 | 0.82 (4) |
C21—C22 | 1.394 (5) | C34—O35 | 1.201 (3) |
C22—O22 | 1.359 (4) | C34—O36 | 1.312 (3) |
C22—C23 | 1.381 (5) | O36—H36 | 0.81 (3) |
C23—C24 | 1.363 (6) | O41—H41 | 0.83 (5) |
C23—H23 | 0.9300 | O41—H42 | 0.88 (5) |
C24—C25 | 1.352 (6) | O51—H51 | 0.98 (2) |
C24—H24 | 0.9300 | O51—H52 | 0.97 (2) |
C2—N1—C6 | 111.9 (3) | C22—C23—H23 | 120.1 |
C2—N1—H11 | 106 (2) | C25—C24—C23 | 120.7 (4) |
C6—N1—H11 | 109 (3) | C25—C24—H24 | 119.7 |
C2—N1—H12 | 110 (2) | C23—C24—H24 | 119.7 |
C6—N1—H12 | 107 (3) | C24—C25—C26 | 120.0 (4) |
H11—N1—H12 | 112 (4) | C24—C25—H25 | 120.0 |
N1—C2—C3 | 109.9 (3) | C26—C25—H25 | 120.0 |
N1—C2—H2A | 109.7 | C21—C26—C25 | 120.9 (4) |
C3—C2—H2A | 109.7 | C21—C26—H26 | 119.6 |
N1—C2—H2B | 109.7 | C25—C26—H26 | 119.6 |
C3—C2—H2B | 109.7 | C22—O22—C27 | 119.4 (3) |
H2A—C2—H2B | 108.2 | O22—C27—H27A | 109.5 |
N4—C3—C2 | 109.8 (3) | O22—C27—H27B | 109.5 |
N4—C3—H3A | 109.7 | H27A—C27—H27B | 109.5 |
C2—C3—H3A | 109.7 | O22—C27—H27C | 109.5 |
N4—C3—H3B | 109.7 | H27A—C27—H27C | 109.5 |
C2—C3—H3B | 109.7 | H27B—C27—H27C | 109.5 |
H3A—C3—H3B | 108.2 | O32—C31—O31 | 125.6 (3) |
C21—N4—C3 | 116.7 (2) | O32—C31—C32 | 116.1 (2) |
C21—N4—C5 | 112.4 (2) | O31—C31—C32 | 118.2 (3) |
C3—N4—C5 | 109.7 (2) | O33—C32—C31 | 112.1 (2) |
N4—C5—C6 | 110.5 (3) | O33—C32—C33 | 109.6 (2) |
N4—C5—H5A | 109.5 | C31—C32—C33 | 109.6 (2) |
C6—C5—H5A | 109.5 | O33—C32—H32A | 108.5 |
N4—C5—H5B | 109.5 | C31—C32—H32A | 108.5 |
C6—C5—H5B | 109.5 | C33—C32—H32A | 108.5 |
H5A—C5—H5B | 108.1 | C32—O33—H33 | 105 (3) |
N1—C6—C5 | 110.4 (3) | O34—C33—C34 | 111.8 (2) |
N1—C6—H6A | 109.6 | O34—C33—C32 | 110.2 (2) |
C5—C6—H6A | 109.6 | C34—C33—C32 | 109.5 (2) |
N1—C6—H6B | 109.6 | O34—C33—H33A | 108.4 |
C5—C6—H6B | 109.6 | C34—C33—H33A | 108.4 |
H6A—C6—H6B | 108.1 | C32—C33—H33A | 108.4 |
C26—C21—C22 | 118.2 (3) | C33—O34—H34 | 110 (3) |
C26—C21—N4 | 123.4 (3) | O35—C34—O36 | 125.5 (3) |
C22—C21—N4 | 118.3 (3) | O35—C34—C33 | 122.5 (3) |
O22—C22—C23 | 123.9 (4) | O36—C34—C33 | 112.0 (2) |
O22—C22—C21 | 115.7 (3) | C34—O36—H36 | 106 (2) |
C23—C22—C21 | 120.5 (3) | H41—O41—H42 | 106 (4) |
C24—C23—C22 | 119.7 (4) | H51—O51—H52 | 106 (3) |
C24—C23—H23 | 120.1 | ||
C6—N1—C2—C3 | −54.9 (4) | C23—C24—C25—C26 | 0.3 (6) |
N1—C2—C3—N4 | 58.6 (4) | C22—C21—C26—C25 | 0.6 (5) |
C2—C3—N4—C21 | 169.1 (3) | N4—C21—C26—C25 | −177.5 (3) |
C2—C3—N4—C5 | −61.7 (3) | C24—C25—C26—C21 | −0.7 (6) |
C21—N4—C5—C6 | −167.9 (3) | C23—C22—O22—C27 | −8.7 (6) |
C3—N4—C5—C6 | 60.6 (3) | C21—C22—O22—C27 | 170.4 (4) |
C2—N1—C6—C5 | 53.7 (4) | O32—C31—C32—O33 | 10.6 (4) |
N4—C5—C6—N1 | −56.1 (4) | O31—C31—C32—O33 | −169.8 (2) |
C3—N4—C21—C26 | 22.6 (4) | O32—C31—C32—C33 | −111.3 (3) |
C5—N4—C21—C26 | −105.3 (3) | O31—C31—C32—C33 | 68.3 (3) |
C3—N4—C21—C22 | −155.5 (3) | O33—C32—C33—O34 | −66.8 (3) |
C5—N4—C21—C22 | 76.6 (3) | C31—C32—C33—O34 | 56.6 (3) |
C26—C21—C22—O22 | −179.1 (3) | O33—C32—C33—C34 | 56.6 (3) |
N4—C21—C22—O22 | −0.9 (4) | C31—C32—C33—C34 | 179.9 (2) |
C26—C21—C22—C23 | 0.0 (5) | O34—C33—C34—O35 | 3.2 (4) |
N4—C21—C22—C23 | 178.2 (3) | C32—C33—C34—O35 | −119.2 (3) |
O22—C22—C23—C24 | 178.6 (4) | O34—C33—C34—O36 | −178.9 (3) |
C21—C22—C23—C24 | −0.4 (5) | C32—C33—C34—O36 | 58.7 (3) |
C22—C23—C24—C25 | 0.3 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H11···O31 | 0.79 (4) | 2.40 (4) | 3.028 (4) | 137 (3) |
N1—H11···O36i | 0.79 (4) | 2.43 (4) | 2.977 (4) | 128 (3) |
N1—H11···O35ii | 0.79 (4) | 2.50 (3) | 2.942 (3) | 117 (3) |
N1—H12···O41 | 0.89 (4) | 1.91 (4) | 2.792 (5) | 168 (3) |
O33—H33···O34iii | 0.77 (4) | 2.14 (4) | 2.800 (3) | 144 (4) |
O34—H34···O31iii | 0.82 (4) | 2.11 (4) | 2.836 (3) | 148 (3) |
O36—H36···O32iv | 0.81 (4) | 1.68 (4) | 2.478 (3) | 167 (3) |
O41—H41···O33v | 0.82 (5) | 1.94 (5) | 2.753 (4) | 167 (3) |
O41—H42···O31i | 0.87 (5) | 1.90 (5) | 2.766 (4) | 169 (3) |
O51—H51···O41 | 0.98 (4) | 1.80 (5) | 2.776 (5) | 172 (9) |
O51—H52···O22i | 0.97 (7) | 2.22 (7) | 3.054 (7) | 144 (6) |
O51—H52···N4i | 0.97 (7) | 2.48 (6) | 3.307 (6) | 143 (5) |
C23—H23···Cg2vi | 0.93 | 2.91 | 3.722 (4) | 147 |
Symmetry codes: (i) x−1, y, z; (ii) −x+2, y+1/2, −z+1; (iii) −x+2, y−1/2, −z+1; (iv) x+1, y, z; (v) x−1, y+1, z; (vi) −x+1, y+1/2, −z. |
Cg1, Cg2 and Cg3 represent the centroids of the rings (C31–C36), (C21–C26) and (C41–C46), respectively. |
Compound | D—H···A | D—H | H···A | D···A | D—H···A |
(I) | N1—H11···O31 | 1.02 (2) | 1.60 (2) | 2.616 (3) | 176 (2) |
N1—H12···O32i | 0.92 (3) | 1.88 (3) | 2.792 (3) | 173 (2) | |
C3—H3A···Cg1i | 0.97 | 2.96 | 3.881 (3) | 160 | |
(II) | N1—H11···O31 | 0.89 (4) | 1.75 (4) | 2.620 (4) | 168 (3) |
N1—H12···O32i | 0.88 (4) | 1.91 (4) | 2.786 (4) | 175 (4) | |
(III) | N1—H11···O31 | 0.88 (2) | 1.83 (2) | 2.684 (3) | 163 (2) |
N1—H11···O32 | 0.88 (2) | 2.60 (2) | 3.060 (3) | 113.6 (17) | |
N1—H12···O32i | 0.91 (3) | 1.84 (3) | 2.746 (3) | 176 (3) | |
C33—H33···O32ii | 0.93 | 2.57 | 3.327 (3) | 139 | |
C2—H2B···Cg2iii | 0.97 | 2.77 | 3.482 (2) | 131 | |
(IV) | N1—H11···O31 | 0.99 (3) | 1.72 (3) | 2.694 (4) | 167 (3) |
N1—H11···O32 | 0.99 (3) | 2.51 (3) | 3.131 (4) | 120.9 (19) | |
N1—H12···O32iii | 0.88 (3) | 1.83 (3) | 2.679 (4) | 161 (3) | |
N1—H11···O41 | 0.99 (3) | 1.77 (5) | 2.67 (4) | 151 (3) | |
N1—H11···O42 | 0.99 (3) | 2.52 (5) | 3.20 (4) | 126 (2) | |
N1—H12···O42iii | 0.88 (3) | 1.83 (5) | 2.63 (4) | 151 (3) | |
C34—H34···Cg2iv | 0.93 | 2.74 | 3.543 (5) | 145 | |
C44—H44···Cg2iv | 0.93 | 2.99 | 3.73 (4) | 137 | |
C26—H26···Cg3v | 0.93 | 2.96 | 3.754 (17) | 144 | |
(V) | N1—H11···O31 | 0.97 (4) | 1.74 (3) | 2.682 (4) | 162 (3) |
N1—H12···O32i | 0.92 (4) | 1.79 (4) | 2.700 (5) | 170 (4) | |
C5—H5B···Cg1ii | 0.97 | 2.87 | 3.554 (4) | 128 | |
C34—H34···Cg2vi | 0.93 | 2.93 | 3.658 (7) | 136 | |
(VI) | N1—H11···O31 | 0.75 (4) | 1.98 (4) | 2.726 (4) | 170 (4) |
N1—H12···O32vii | 0.88 (3) | 1.86 (3) | 2.712 (4) | 163(3 | |
C25—H25···O32viii | 0.93 | 2.56 | 3.488 (4) | 173 | |
C26—H26···Cg1viii | 0.93 | 2.93 | 3.697 (4) | 141 | |
(VII) | N1—H11···O31 | 0.89 | 1.80 | 2.66 (3) | 162 |
N1—H11···O33 | 0.89 | 1.93 | 2.80 (3) | 165 | |
N1—H12···O31ix | 0.89 | 1.97 | 2.83 (3) | 162 | |
N1—H12···O33ix | 0.89 | 1.74 | 2.60 (3) | 161 | |
C25—H25···O34x | 0.93 | 2.50 | 3.43 (3) | 174 | |
C26—H26···Cg1x | 0.93 | 2.93 | 3.716 (5) | 143 | |
(VIII) | N1—H11···O31 | 1.010 (15) | 1.673 (15) | 2.6696 (19) | 168.6 (13) |
N1—H12···O32i | 0.963 (16) | 1.745 (16) | 2.7077 (17) | 178.2 (10) | |
(IX) | N1—H11···O31 | 1.068 (15) | 1.547 (15) | 2.6048 (15) | 169.7 (14) |
N1—H12···O32i | 0.942 (15) | 1.861 (15) | 2.7797 (15) | 164.4 (14) | |
N34—H34···O32xi | 0.914 (16) | 2.155 (16) | 3.0535 (18) | 167.5 (14) | |
(X) | N1—H11···O31 | 0.974 (16) | 1.677 (16) | 2.6500 (19) | 176.8 (15) |
N1—H11···O32 | 0.974 (16) | 2.581 (17) | 3.2169 (17) | 123.0 (12) | |
N1—H12···O32i | 0.948 (17) | 1.837 (17) | 2.7709 (18) | 168.2 (16) | |
(XI) | N1—H11···O31 | 0.929 (16) | 1.771 (16) | 2.6837 (16) | 166.8 (15) |
N1—H12···O41 | 0.911 (16) | 1.939 (16) | 2.8324 (19) | 165.5 (14) | |
O41—H41···O32xii | 0.84 (2) | 1.99 (2) | 2.8156 (19) | 168 (2) | |
O41—H42···O51 | 0.90 (2) | 1.91 (2) | 2.810 (2) | 172 (2) | |
O51—H51···O31i | 0.90 (2) | 1.91 (2) | 2.810 (2) | 172 (2) | |
O51—H52···O22xii | 0.77 (2) | 2.25 (2) | 2.9544 (19) | 153 (2) | |
C25—H25···O36i | 0.93 | 2.58 | 3.433 (2) | 153 | |
(XII) | N1—H11···O33 | 0.868 (18) | 2.224 (18) | 2.9120 (19) | 136.1 (16) |
N1—H12···O31i | 0.900 (18) | 1.833 (18) | 2.7142 (18) | 165.9 (16) | |
N1—H12···O32i | 0.900 (19) | 2.593 (17) | 3.154 (2) | 121.2 (13) | |
C6—H6A···O34xiii | 0.97 | 2.56 | 3.423 (2) | 148 | |
(XIII) | O33—H33···O32 | 1.07 (2) | 1.37 (2) | 2.4447 (16) | 177.7 (16) |
O43—H43···O42 | 1.00 (2) | 1.48 (2) | 2.4707 (17) | 174.0 (17) | |
N11—H111···O32 | 0.927 (17) | 1.891 (17) | 2.8122 (18) | 172.3 (16) | |
N11—H112···O41xiv | 0.930 (17) | 1.848 (17) | 2.7725 (17) | 172.9 (13) | |
N21—H211···O42 | 0.975 (15) | 1.821 (15) | 2.7926 (16) | 174.5 (14) | |
N21—H212···O31 | 0.895 (15) | 2.283 (15) | 2.9776 (17) | 134.4 (12) | |
N21—H212···O34xv | 0.895 (15) | 2.428 (15) | 3.1170 (18) | 134.1 (12) | |
C16—H16A···O34xv | 0.97 | 2.55 | 3.341 (2) | 138 | |
C16—H16B···O44xv | 0.97 | 2.52 | 3.338 (2) | 141 | |
C25—H25B···Cg4xvi | 0.97 | 2.92 | 3.8440 (16) | 159 | |
(XIV) | N1—H11···O31 | 0.89 | 2.01 | 2.894 (5) | 171 |
N1—H11···O33 | 0.89 | 1.73 | 2.584 (7) | 160 | |
N1—H12···O41 | 0.89 | 1.97 | 2.8251 (15) | 161 | |
O32—H32···O32xvii | 0.82 | 1.54 | 2.355 (7) | 176 | |
O34—H34···O34xvii | 0.82 | 2.03 | 2.820 (9) | 161 | |
O42—H42···O42xviii | 0.82 | 1.62 | 2.4352 (12) | 177 | |
(XV) | N1—H11···O31 | 0.79 (4) | 2.40 (4) | 3.028 (4) | 137 (3) |
N1—H11···O36xii | 0.79 (4) | 2.43 (4) | 2.977 (4) | 128 (3) | |
N1—H11···O35xix | 0.79 (4) | 2.50 (3) | 2.942 (3) | 117 (3) | |
N1—H12···O41 | 0.89 (4) | 1.91 (4) | 2.792 (5) | 168 (3) | |
O33—H33···O34xx | 0.77 (4) | 2.14 (4) | 2.800 (3) | 144 (4) | |
O34—H34···O31xx | 0.82 (4) | 2.11 (4) | 2.836 (3) | 148 (3) | |
O36—H36···O32ii | 0.81 (4) | 1.68 (4) | 2.478 (3) | 167(3 | |
O41—H41···O33xxi | 0.82 (5) | 1.94 (5) | 2.753 (4) | 167 (3) | |
O41—H42···O31xii | 0.87 (5) | 1.90 (5) | 2.766 (4) | 169 (3) | |
O51—H51···O41 | 0.98 (4) | 1.80 (5) | 2.776 (5) | 172 (9) | |
O51—H52···O22xii | 0.97 (7) | 2.22 (7) | 3.054 (7) | 144 (6) | |
O51—H52···N4xii | 0.97 (7) | 2.48 (6) | 3.307 (6) | 143 (5) | |
C23—H23···Cg2xxii | 0.93 | 2.91 | 3.722 (4) | 147 |
Symmetry codes: (i) 1 - x, 1 - y, 1 - z; (ii) 1 + x, y, z; (iii) x, 1 - y, -1/2 + z; (iv) -1/2 + x, 3/2 - y, -1/2 + z; (v) 1/2 + x, -1/2 + y, z; (vi) -1 + x, y, 1 + z; (vii) 1/2 + x, 1/2 - y, 1 - z; (Viii) 1/2 - x, 1 - y, -1/2 + z; (ix) -1/2 + x, 3/2 - y, 1 - z; (x) 3/2 - x, 1 - y, 1/2 + z; (xi) x, 1/2 - y, -1/2 + z; (xii) -1 + x, y, z; (xiii) x, 1 + y, z; (xiv) x, -1 + y, z; (xv) -x, 1 - y, 1 - z; (xvi) 1 - x, -y, -z; (xvii) 1 - x, 1 - y, 2 - z; (xviii) 1 - x, -y, 2 - z; (xix) 2 - x, 1/2 + y, 1 - z; (xx) 2 - x, -1/2 + y, 1 - z; (xxi) -1 + x, 1 + y, z; (xxii) 1 - x, 1/2 + y, -z. |
Acknowledgements
CHC thanks the University of Mysore for research facilities.
Funding information
HSY thanks the University Grants Commission, New Delhi for the award of a BSR Faculty Fellowship for three years.
References
Acosta, L. M., Bahsas, A., Palma, A., Cobo, J., Hursthouse, M. B. & Glidewell, C. (2009). Acta Cryst. C65, o92–o96. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Etter, M. C. (1990). Acc. Chem. Res. 23, 120–126. CrossRef CAS Web of Science Google Scholar
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256–262. CrossRef ICSD CAS Web of Science IUCr Journals Google Scholar
Ferguson, G., Glidewell, C., Gregson, R. M. & Meehan, P. R. (1998a). Acta Cryst. B54, 129–138. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Ferguson, G., Glidewell, C., Gregson, R. M. & Meehan, P. R. (1998b). Acta Cryst. B54, 139–150. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Ferguson, G., Glidewell, C. & Patterson, I. L. J. (1996). Acta Cryst. C52, 420–423. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Gregson, R. M., Glidewell, C., Ferguson, G. & Lough, A. J. (2000). Acta Cryst. B56, 39–57. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Hackling, A., Ghosh, R., Perachon, S., Mann, A., Höltje, H. D., Wermuth, C. G., Schwartz, J. C., Sippl, W., Sokoloff, P. & Stark, H. (2003). J. Med. Chem. 46, 3883–3899. CrossRef PubMed CAS Google Scholar
Harish Chinthal, C., Yathirajan, H. S., Archana, S. D., Foro, S. & Glidewell, C. (2020). Acta Cryst. E76, 841–847. Web of Science CrossRef IUCr Journals Google Scholar
Harish Chinthal, C., Yathirajan, H. S., Kavitha, C. N., Foro, S. & Glidewell, C. (2020). Acta Cryst. E76, 1179–1186. CrossRef IUCr Journals Google Scholar
Kiran Kumar, H., Yathirajan, H. S., Foro, S. & Glidewell, C. (2019). Acta Cryst. E75, 1494–1506. Web of Science CSD CrossRef IUCr Journals Google Scholar
Kiran Kumar, H., Yathirajan, H. S., Harish Chinthal, C., Foro, S. & Glidewell, C. (2020). Acta Cryst. E76, 488–495. Web of Science CSD CrossRef IUCr Journals Google Scholar
Kiran Kumar, H., Yathirajan, H. S., Sagar, B. K., Foro, S. & Glidewell, C. (2019). Acta Cryst. E75, 1253–1260. Web of Science CSD CrossRef IUCr Journals Google Scholar
Orjales, A., Alonso-Cires, L., Labeaga, L. & Corcóstegui, R. (1995). J. Med. Chem. 38, 1273–1277. CrossRef CAS PubMed Google Scholar
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England. Google Scholar
Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249–259. Web of Science CrossRef CAS IUCr Journals Google Scholar
Riddell, F. G. & Rogerson, M. (1996). J. Chem. Soc. Perkin Trans. 2, pp. 493–504. CrossRef Web of Science Google Scholar
Riddell, F. G. & Rogerson, M. (1997). J. Chem. Soc. Perkin Trans. 2, pp. 249–256. CrossRef Web of Science Google Scholar
Seip, H. M. & Seip, R. (1973). Acta Chem. Scand. 27, 4024–4027. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Shreekanth, T. K., Yathirajan, H. S., Kalluraya, B., Foro, S. & Glidewell, C. (2020). Acta Cryst. E76, 1605–1610. CrossRef IUCr Journals Google Scholar
Spek, A. L. (2020). Acta Cryst. E76, 1–11. Web of Science CrossRef IUCr Journals Google Scholar
Verdonk, M. L., Voogd, J. W., Kanters, J. A., Kroon, J., den Besten, R., Brandsma, L., Leysen, D. & Kelder, J. (1997). Acta Cryst. B53, 976–983. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Waszkielewicz, A. M., Pytka, K., Rapacz, A., Wełna, E., Jarzyna, M., Satała, G., Bojarski, A. J., Sapa, J., Żmudzki, P., Filipek, B. & Marona, H. (2015). Chem. Biol. Drug Des. 85, 326–335. CrossRef CAS PubMed Google Scholar
Wood, P. A., Allen, F. H. & Pidcock, E. (2009). CrystEngComm, 11, 1563–1571. Web of Science CrossRef CAS Google Scholar
Yépes, A. F., Palma, A., Marchal, A., Cobo, J. & Glidewell, C. (2012). Acta Cryst. C68, o199–o203. Web of Science CSD CrossRef IUCr Journals Google Scholar
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