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research papers
Supramolecular structures of 1-phenylethylammonium tartrates
aSchool of Chemistry, University of St Andrews, St Andrews, Fife KY16 9ST, Scotland, bCCLRC Daresbury Laboratory, Daresbury, Warrington WA4 4AD, England, cLash Miller Chemical Laboratories, University of Toronto, Toronto, Ontario, Canada M5S 3H6, and dDepartment of Chemistry, University of Guelph, Guelph, Ontario, Canada N1G 2W1
*Correspondence e-mail: cg@st-andrews.ac.uk
The structures of six 1-phenylethylammonium tartrates have been determined and in each of them a distinctive hydrogen-bonded anion S)-1-Phenylethylammonium (R,R)-hydrogen tartrate [(I), P21, Z′ = 1] contains anion sheets built from a single type of ring with cations pendent, via three N—H⋯O hydrogen bonds, from just one face of the sheet. (S)-1-Phenylethylammonium rac-hydrogen tartrate [(II), P21, Z′ = 2] and its (R)-1-phenylethylammonium rac-hydrogen tartrate [(III), P21, Z′= 2] contain anion sheets built from four types of ring,
,
,
and
, and there are cations pendent from both faces of the sheet. The anion in bis[(S)-1-phenylethylammonium] (R,R)-tartrate [(IV), P21, Z′ = 1] consists of simple C(5) chains, which are linked into sheets by the cations, while in bis(rac-1-phenylethylammonium) (R,R)-tartrate [(V), P21, Z′ = 2] there are anion sheets containing two distinct types of
ring, with equal numbers of (R) and (S) cations pendent from each face of the anion sheet. Bis[(R)-1-phenylethylammonium] rac-tartrate methanol hemisolvate [(VI), P1, Z′ = 4, with 14 independent components in the asymmetric unit] contains anion sheets built from two types of
ring and two types of
ring; half of the cations and half of the methanol molecules are pendent from each face of the sheet.
1. Introduction
We have recently reported the supramolecular structures of the tartrate salts formed by a range of simple achiral diamines (Farrell et al., 2002a) and one of the aims of that study was the comparison of cognate pairs of salts formed by the same amine, on the one hand with racemic tartaric acid and on the other with (2R,3R)-tartaric acid. In those cases where the racemic and acids formed pairs of salts with a common stoichiometry, the overall supramolecular structures of the two salts were very similar, despite their generally different space groups. Moreover, the salts formed by the (2R,3R) acid closely mimic centrosymmetry in a number of cases, a phenomenon also noted in the analogous salts formed by (S)-malic acid with a comparable range of achiral diamines (Farrell et al., 2002b
). Another feature of interest in the tartrate structures was the very wide range of anion substructures observed, including a variety of chains of fused rings and a variety of sheet substructures, as well as three-dimensional frameworks of anions encapsulating large voids which enclose the cations.
In view of this variety of anion substructures, but more particularly in view of the common mimicry of centrosymmetry, we have now extended this study to encompass systems in which the amine component is also chiral and for this purpose we have selected 1-phenylethylamine, PhCH(CH3)NH2, which is readily available in both forms, (R) and (S), as well as in the racemic form. Using the various stereochemical forms of this amine in combination with the various forms of tartaric acid, we have now prepared a range of 1:1 and 2:1 salts (I)–(VI), whose supramolecular structures we discuss here. The structure of (I) has previously been determined using ambient-temperature data (Molins et al., 1989
), but no analysis or discussion of the supramolecular aggregation was reported.
2. Experimental
2.1. Synthesis
Samples of racemic 1-phenylethylamine and R)- and (S)-1-phenylethylamine, and of racemic tartaric acid and (R,R)-tartaric acid were purchased from Aldrich, and all were used as received. For the preparation of the phenylethylammonium tartrate salts, stoichiometric quantities of the appropriate amine and acid were separately dissolved in methanol. These solutions were then mixed and the mixtures were set aside to crystallize, providing analytically pure samples within a few days. Analyses: found for (I): C 53.1, H 6.7, N 5.1%; for (II): C 53.4, H 6.4, N 5.1%; for (III): C 52.7, H 6.4, N 5.0%: C12H17NO6 requires C 53.1, H 6.3, N 5.2%: found for (IV): C 60.8, H 7.1, N 6.9%; for (V): C 60.3, H 7.2, N 7.0%; C20H28N2O6 requires C 61.2, H 7.2, N 7.1%: for (VI): C 60.1, H 7.4, N 6.8; C41H60N4O13 requires C 60.3, H 7.4, N 6.9%. For all except (V), satisfactory crystals suitable for single-crystal X-ray diffraction were selected directly from the prepared samples. For (V) the crystals were consistently of poor quality, despite a number of preparations under different conditions, and no useful data were obtained using a conventional laboratory radiation source; however, by use of synchrotron radiation a satisfactory dataset was obtained.
(2.2. Data collection, structure solution and refinement
Diffraction data for (I)–(VI) were collected at 150 (1) K using Nonius Kappa-CCD diffractometers with, for (I)–(IV) and (VI), graphite-monochromated Mo Kα radiation (λ = 0.71073 Å) and, for (V), synchrotron radiation (λ = 0.69000 Å). Other details of cell data, data collection and are summarized in Table 1, together with details of the software employed (Farrugia, 1999
; Ferguson, 1999
; Nonius, 1997
; Otwinowski & Minor, 1997
; Sheldrick, 1997
; Spek, 2003
). For (I)–(V) the permitted P21 and P21/m as possible space groups: in each case P21 was selected and confirmed by the structure analysis. Crystals of (VI) are triclinic and the P1 was selected, and confirmed by the structure analysis. The structures were solved by and refined with all data on F2. A weighting scheme based upon P = [Fo2 + 2Fc2]/3 was employed in order to reduce statistical bias (Wilson, 1976
). All H atoms were located from difference maps and all were fully ordered. All H atoms were treated as riding atoms with distances C—H 0.95 (aromatic), 0.98 (methyl) or 1.00 (aliphatic CH), N—H 0.91 and O—H 0.84 Å.
|
Supramolecular analyses were made and the diagrams were prepared with the aid of PLATON (Spek, 2003). Details of hydrogen-bond dimensions are given in Table 2
.1 Figs. 1–16
show the ionic components, with the atom-labelling schemes, and aspects of the supramolecular structures.
|
![]() | Figure 1 The independent components of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. |
![]() | Figure 2 The independent components of (III) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. |
![]() | Figure 3 The independent components of (IV) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. |
![]() | Figure 4 The independent components of (V) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. |
![]() | Figure 5 The independent components of (VI) showing the atom-labelling scheme: (a) the four independent anions and the two methanol molecules; (b)–(i) the eight independent cations. Displacement ellipsoids are drawn at the 30% probability level. |
![]() | Figure 6 Part of the crystal structure of (I) showing the formation of a (010) sheet of anions with cations pendent from it. For the sake of clarity, the H atoms bonded to the C atoms are omitted, as are the phenyl and methyl groups in the cation. The atoms marked with an asterisk (*), a hash (#), a dollar sign ($) or an ampersand (&) are at the symmetry positions (x, y, -1 + z), (-1 + x, y, z), (1 + x, y, z) and (1 + x, y, 1 + z), respectively. |
![]() | Figure 7 Part of the crystal structure of (III), showing the formation by the anions of a (010) sheet containing four different types of ring. For the sake of clarity, the H atoms bonded to the C atoms are omitted, as are the intra-anion O—H⋯O hydrogen bonds. The atoms marked with an asterisk (*), a hash (#), a dollar sign ($) or an ampersand (&) are at the symmetry positions (x, y, 1 + z), (x, y, -1 + z), (1 + x, y, z) and (-1 + x, y, z), respectively. |
![]() | Figure 8 Part of the crystal structure of (IV) showing the formation of the C(5) anion chains parallel to [100] and their linking into (001) sheets by the cations. For the sake of clarity, the H atoms bonded to the C atoms are omitted, as are the methyl and phenyl groups in the cations and the intra-anion O—H⋯O hydrogen bonds. The atoms marked with an asterisk (*), a hash (#), a dollar sign ($) or an ampersand (&) are at the symmetry positions (-1 + x, y, z), (1 + x, y, z), ( ![]() ![]() |
![]() | Figure 9 Part of the crystal structure of (V) showing the formation of a (010) anion sheet built from two types of ![]() |
![]() | Figure 10 Part of the crystal structure of (VI) showing the formation of a (001) anion sheet built from two types of ![]() ![]() |
![]() | Figure 11 Stereoview of part of the crystal structure of (I) showing the cations pendent from a single face of the anion sheet. For the sake of clarity, the H atoms bonded to the C atoms have been omitted. |
![]() | Figure 12 Projection of part of the crystal structure of (III) showing the tripartite (010) layers with cations linked to both faces of the anion sheet. For the sake of clarity, the H atoms bonded to the C atoms have been omitted. |
![]() | Figure 13 Projection of part of the crystal structure of (V) showing one of the tripartite (010) layers with cations linked to both faces of the anion sheet. For the sake of clarity, the H atoms bonded to C atoms have been omitted. |
![]() | Figure 14 Stereoview of part of the crystal structure of (VI) showing the tripartite sheets and the pendent methanol molecules. For the sake of clarity, the H atoms bonded to C atoms have been omitted. |
![]() | Figure 15 Projection of part of the crystal structure of (IV) showing the cations linked to both faces of the anion sheet, and the action of the 21 screw axes in causing alternation of the cations between the two faces. For the sake of clarity, the H atoms bonded to C atoms have been omitted. |
![]() | Figure 16 Stereoview of part of the crystal structure of (III) showing the [010] chain built from C—H⋯π(arene) hydrogen bonds which links the (010) sheets. For the sake of clarity the H atoms not involved in the motif shown have been omitted. |
3. Results and discussion
3.1. Crystallization characteristics
Crystallization from methanol solutions of equimolar mixtures of 1-phenylethylamine and tartaric acid gives, regardless of whether the compounds are 3)NH3]+·[HOCOCH(OH)CH(OH)COO]−, in which complete transfer of a single H atom from the acid component to the basic components has occurred.
or racemic mixtures, salts of the composition [PhCH(CHWhen R,R)-acid, the salt (I) was produced in which the (Fig. 1) consists of just one cation and one anion. The identical salt was identified as the sole crystalline product from the cocrystallization of the racemic amine and the (R,R)-acid, so that complete in crystallization is apparent with no (R) configuration cations present in the crystalline salt. It is of interest to note in this context that no crystalline product of consistent composition could be obtained from cocrystallizations of (R)-amine with (R,R)-acid: this observation is entirely consistent with the behaviour reported by Molins et al. (1989
), who were also unable to obtain any crystalline product from this combination of amine and acid.
On the other hand, when the S)-amine was cocrystallized with racemic tartaric acid, the product (II) was found to have an containing two cations, both of (S) configuration, and two anions, one each of (R,R) and (S,S) configuration. The enantiomorphous compound (III) was obtained from (R)-amine and the racemic acid. Hence, although the acid exerts selectivity on the racemic amine in the formation of (I), the amine has not exerted any selectivity in the formation of (II) and (III). The for (III) is rather better than that for (II) and hence we discuss only (III) (Fig. 2) hereafter.
When the initial crystallization mixtures contained a 2:1 molar ratio of amine to acid, the resulting salts all had the composition [{PhCH(CH3)NH3}+]2·[OOCCH(OH)CH(OH)COO]2−, again regardless of whether or racemic components were employed. Cocrystallization of such a 2:1 mixture containing (S)-amine and (R,R)-acid yielded a product (IV) containing two cations and one anion in the (Fig. 3). In contrast to the behaviour of the 1:1 mixture producing (I), a 2:1 mixture of racemic amine and (R,R)-acid gave a product (V) in which the (Fig. 4
) consists of four cations, two each of (R) and (S) configurations, and two anions, so that no is apparent here.
Each of the salts (I)–(V) crystallizes in the P21. However, the salt (VI) produced from a 2:1 mixture of (R)-amine and racemic tartaric acid crystallizes in the P1 and its (Fig. 5) contains eight cations and four anions, of which two each have (R,R) and (S,S) configurations, together with two methanol molecules. A product (VII) of identical composition was isolated from a 2:1 mixture of the (S)-amine and racemic tartaric acid, but no crystals suitable for single-crystal X-ray diffraction have yet been obtained.
3.2. Structure solutions
Although in each of (I)–(VI) the ) was wholly inconclusive (Flack & Bernardinelli, 2000
) because of the very low characteristic of the light elements C, N and O, nonetheless, in every case the initial structure solution, obtained using System-S in PLATON (Spek, 2003
), corresponded to the correct of the component present.
Struck by this rather unexpected result, we have now reviewed our initial structure solutions for some recently completed series of light-atom structures containing et al., 2002a,b
; Bowes et al., 2003b
; Turkington et al., 2004
). In a total of 17 structures, including those reported here, each having a containing an component of previously known configuration, the initial structure solution using System-S gave the correct in every case, without exception.
3.3. Intra-anion hydrogen bonds
The intra-anion hydrogen bonding (Table 2), in principle the simplest aspect of the hydrogen bonding, nonetheless shows several variants, several of which are not readily predictable. In the independent anion of (III), and in three of the four independent anions in (VI), there is a single intra-anion hydrogen bond and in every case the acceptor is a carboxylate O atom. In the fourth anion in (VI), no such bond occurs nor is there any such bond in either of the anions in (V). In (I) and (IV), on the other hand, both hydroxyl groups in the anion form intra-anion hydrogen bonds; in (I) both acceptors are carboxyl O atoms, while for (III) the acceptor in one interaction is a carboxylate O, as usual, while in the other it is the second hydroxyl O. For none of these hydrogen bonds does the O—H⋯O angle exceed 120°, so that the interaction energies may well be fairly small: however, the entropic cost of these interactions is almost negligible and they may well have a significant influence on the overall anion conformations.
3.4. Anion substructures
In the supramolecular structures of each of (I)–(VI) there is a clearly identifiable
built from only the anions. It is convenient to approach the overall analysis of the supramolecular structures firstly in terms of these anion substructures and then to consider how the cations, and in (VI) only the methanol molecules, are linked to the anion substructure.3.4.1. Compound (I)
The anions in (I) form a two-dimensional x, y, z) acts as a donor to carboxylate O1 in the anion at (x, y, -1 + z) in a very short hydrogen bond, so generating a C(7) (Bernstein et al., 1995) chain running parallel to the [001] direction. The hydroxyl O5, as well as acting as a hydrogen-bond donor to O2 within the anion, also acts as a donor to carbonyl O4 in the anion at (-1 + x, y, z), in a planar three-centre O—H⋯(O)2 system, so generating a C(6) chain parallel to [100]. The combination of the [100] and [001] chains generates a (010) sheet in the form of a (4,4) net (Batten & Robson, 1998
) built from a single type of
ring (Fig. 6
). The reference anion sheet lies in the domain 0.27 < y < 0.47 and a second such sheet, related to the first by the action of the 21 screw axis, lies in the domain 0.77 < y < 0.97.
3.4.2. Compound (III)
The two independent anions in (III) form a two-dimensional ), hydroxyl atoms O16 and O26 act as hydrogen-bond donors, respectively, to carboxylate atoms O21 and O11, and these
dimers are linked by two further pairs of O—H⋯O hydrogen bonds into chains of edge-fused rings running along the [100] and [001] directions. Carboxyl atoms O14 and O24 in the anion pair at (x, y, z) act as donors, respectively, to carboxylate atoms O11 at (1 + x, y, z) and O21 at (-1 + x, y, z), thereby generating by translation a chain of edge-fused, alternating
and
rings, in which the carboxylate atoms O11 and O21 both act as double acceptors of O—H⋯O hydrogen bonds. In addition, the two hydroxyl atoms O15 and O25 at (x, y, z) act as donors, respectively, to carboxylate atoms O22 at (x, y, 1 + z) and O12 at (x, y, -1 + z), thereby generating by translation a second chain of edge-fused rings, this time running parallel to the [001] direction and containing alternating
and
rings. The combination of the [100] and [001] chains generates a (010) sheet built from four different types of ring,
,
,
and
(Fig. 7
). The first two ring types each involve one (2R,3R) anion and one (2S,3S) anion, while the latter two types involve two anions of each hand; each ring is therefore approximately, but not crystallographically, centrosymmetric. The hydrogen-bonded anion sheet is modestly reinforced by an antiparallel and nearly centrosymmetric carbonyl–carbonyl interaction involving the groups C14=O13 and C24=O23 in the anions at (x, y, z) and (1 + x, y, z), respectively. The distances O13⋯C14i and C14⋯O23i [symmetry code (i) 1 + x, y, z] are 2.887 (3) and 2.865 (3) Å, respectively, with angles C14—O13⋯C24i and C14⋯O23i—C24i of 92.9 (2) and 94.2 (2)°, respectively, hence forming an almost ideal type-II interaction (Allen et al., 1998
). The reference anion sheet lies in the domain 0.38 < y < 0.59, with the
anion dimers all centred at around y = 0.50; the immediately adjacent sheets, related to the first by the action of the 21 screw axis, lie in the domain −0.12 < y < 0.09 and 0.88 < y < 1.09, with their
anion dimers centred at around y = 0.0 and y = 1.0, respectively.
3.4.3. Compound (IV)
The anion x, y, z) acts as a hydrogen-bond donor to the carboxylate atom O1 in the anion at (1 + x, y, z), so generating by translation a C(5) chain running parallel to the [100] direction (Fig. 8). This chain lies in the domain 0.54 < y < 0.85, and a second chain, related to the first by the action of the 21 screw axis, lies in the domain 0.04 < y < 0.35: the [100] chains are linked into sheets by the two types of cation.
3.4.4. Compound (V)
In (V) there are two independent tartrate anions, albeit both with the (R,R) configuration, and there are four independent O—H⋯O hydrogen bonds which link the anions into sheets generated by translation. With the (Fig. 4), the hydroxyl atom O25 acts as a hydrogen-bond donor to the carboxylate atom O11. The hydroxyl atom O15 in the anion pair at (x, y, z) acts as a donor to the carboxylate atom O22 in the anion pair at (1 + x, y, z), thus generating by translation a C22(10) chain running parallel to the [100] direction. Similarly, the hydroxyl atom O16 at (x, y, z) acts as a donor to the carboxylate atom O23 at (x, y, 1 + z), so generating a second chain by translation, this time of C22(12) type and running parallel to the [001] direction. Finally, the hydroxyl atom O26 at (x, y, z) acts as a donor to the carboxylate atom O13 at (-1 + x, y, -1 + z), thus generating by translation a second C22(12) motif, now running parallel to the [101] direction. The combination of these three translational chain motifs generates a (010) sheet of anions characterized by two different types of
ring (Fig. 9
).
This reference sheet of anions lies within the domain 0.42 < y < 0.59 and a second such sheet, related to the first by the action of the 21 screw axes, lies in the domain −0.08 < y < 0.09. The large spaces between the nearly planar anion layers are occupied by the cations.
3.4.5. Compound (VI)
Despite the presence of 14 independent components in the ), the four independent anions together generate a fairly simple two-dimensional from which all of the other components, both cations and neutral methanol molecules, are pendent.
Within the anion sheet there are eight independent inter-anion O—H⋯O hydrogen bonds all involving hydroxyl O as the donor and carboxylate O as the acceptor. Four of these hydrogen bonds link pairs of anions, each comprising one (R,R) anion and one (S,S) anion, into two almost centrosymmetric dimers, and the other four O—H⋯O hydrogen bonds link the dimers into a continuous sheet. Atoms O16 and O26 act as donors, respectively, to atoms O21 and O11, thus generating a nearly centrosymmetric dimer, which we denote as the type A dimer, whose centroid is close to (0.25, 0.25, 0.5): similarly, atoms O36 and O46 act as donors, respectively, to atoms O41 and O31, thus generating a second nearly centrosymmetric
dimer, denoted as type B, whose centroid is close to (0.75, 0.75, 0.5).
The inter-dimer hydrogen bonds are so arranged that each type A dimer acts as a donor to two type B dimers and as an acceptor from two further type B dimers, while each type B dimer is similarly linked to four different type A dimers. Thus, for example, in the type A dimer at approximately (0.25, 0.25, 0.5), atoms O25 and O15 act as donors, respectively, to the atoms O44 at (x, -1 + y, z) and O34 at (-1 +x, y, z), which lie in the type B dimers at approximately (0.75, −0.25, 0.5) and (−0.25, 0.75, 0.5), respectively: similarly, atoms O14 and O24 in the type A dimer at approximately (0.25, 0.25, 0.5) accept hydrogen bonds, respectively, from atoms O35 at (x, y, z) and O45 at (-1 + x, -1 + y, z), which lie in the type B dimers at approximately (0.75, 0.75, 0.5) and (−0.25, −0.25, 0.5), respectively. In this manner, the two types of dimer are linked into a (001) sheet containing two independent rings within the dimers and two independent
rings between the dimers. If the individual anions are taken to be the nodes of the resulting net, this is of the (6,3) type (Batten & Robson, 1998
), while if the pseudosymmetric dimers are taken as the nodes the net is of the (4,4) type (Fig. 10
). Just one sheet of this type passes through each occupying only about one-third of the domain of z: for the selected location of the the sheet occupies the domain 0.34 < z < 0.68.
3.5. Linking of the cations to the anion substructures
In each of (I), (III), (V) and (VI) the cations are linked to anion sheets, whereas in (IV) the cations link anion chains into sheets; it is convenient to discuss these two structure types separately. In each of these compounds the [PhCH(CH3)NH3]+ cations act as threefold donors in N—H⋯O hydrogen bonds and each cation is linked to three different anions (Table 2): the majority of these hydrogen bonds are of two-centre type, but three-centre N—H⋯(O)2 systems occur in (III)
3.5.1. Compounds (I), (III), (V) and (VI)
In each of these compounds the three anions which are directly hydrogen-bonded to a given cation form part of the same sheet: however, the orientation of the organic parts of the cations is not the same in each compound. The cations in (I) are all of the (S) configuration and all are hydrogen-bonded to just one face of the anion sheet (Fig. 6), so that viewed along the plane of the anion sheet the structure appears to consist of alternating slabs of cations and anions (Fig. 11
). In (III), by contrast, there are cations pendent from both faces of the anion sheet (Fig. 7
), although all have the same (R) configuration, with all of the type 1 cations containing N3 pendent from one face and all of the type 2 containing N4 cations pendent from the opposite face. Hence, each (010) layer is tripartite with a polar central layer containing all the hydrogen bonds and two lipophilic outer layers (Fig. 12
).
In (V) the cations are again pendent from both faces of the anion sheet (Fig. 9), however, there are cations of both (R) and (S) configurations bonded to both faces. The cations containing N3 and N4, which have the (R) and (S) configurations, respectively, are pendent from one face, while the cations containing N5 and N6, again of (R) and (S) configurations, respectively, are pendent from the opposite face: hence, a tripartite layer is again generated (Fig. 13
). All of the cations in (VI) have the (R) configuration and four cations are pendent from each face of the sheet: those containing N5, N8, N1 and N12 are pendent from one face, and those containing N6, N7, N9 and N10 are pendent from the other face (Fig. 14
).
3.5.2. Compound (IV)
The anion 1 screw axes is to cause an alternation of each type of cation, both of (S) configuration, between the two faces of these sheets.
in (IV) consists of simple [100] chains generated by translation and the action of the cations is to link these chains into sheets, while the action of the 2The ammonium atom N1 at (x, y, z) acts as a hydrogen-bond donor, via H1B, to atom O4 in the anion at (x, y, z), which lies in the reference [100] chain, and via H1A and H1C to atoms O2 in the anion at () and O1 in the anion at
), both of which lie in an adjacent [100] chain related to the first chain by the action of the 21 screw axes. Atom N2 at (x, y, z) acts as a donor, via H2A and H2C, to atoms O4 in the anion at (x, y, z) and O3 in the anion at (-1 + x, y, z), respectively, which both lie in the reference anion chain, and via H2B, to atom O2 in the anion at (
), which lie in the adjacent chain referred to previously. In this way the two cations at (x, y, z) are each hydrogen bonded to the same pair of anion chains and propagation of these interactions by the 21 screw axes then links the anion chains and the cations into a (001) sheet (Fig. 8
). The reference cations containing N1 and N2 have their PhCH(CH3)— fragments on opposite sides of the sheet, but the action of the screw axes means that there are equal numbers of each of the two cation types on both sides of the sheet (Fig. 15
).
3.6. Linking of the sheets in (III)
In none of the compounds described here are there any aromatic π⋯π stacking interactions, but in (III) only there is a single C—H⋯π(arene) hydrogen bond, whose effect is to link the adjacent tripartite (010) sheets into a continuous framework structure. The aromatic atom C36 in the type 1 cation at (x, y, z), which is pendent from the anion sheet in the domain 0.38 < y < 0.59, acts as a hydrogen-bond donor to the ring C41–C46 in the type 2 cation at (), which is pendent from the anion sheet in the domain −0.12 < y < 0.09, so forming a chain running parallel to the [010] direction and generated by the 21 screw axis along (0.5, y, 0.5), which serves to link each (010) sheet to the two adjacent sheets (Fig. 16
).
3.7. (S)-1-Phenylethylammonium meso-hydrogen tartrate
This compound crystallizes in the P21 in a very similar to that of (I) (Table 1), but with the anion in an almost centrosymmetric configuration (Kroon et al., 1984
): although no analysis of the supramolecular structure appears in this report, the reported atom coordinates indicate both similarities to, and differences from, that of (I). As in (I), the anions are linked into hydrogen-bonded (010) sheets and the cations are pendent from just one face of this sheet. However, whereas in (I) the sheets contain just a single type of
ring, in the meso-tartrate analogue the sheets contain alternating
and
rings.
3.8. (R)-Histidinium (R,R)-hydrogen tartrate
The supramolecular structure of (R)-histidinium (R,R)-hydrogen tartrate has been reported very recently (Johnson & Feeder, 2004). In this salt, which crystallizes in the P1 with Z′ = 1, the anions form (010) sheets of
, formed in a manner entirely similar to those in (I) (see §3.4.1
), with one-dimensional substructures in the form of C(6) and C(7) chains along [100] and [010], respectively, although in (I) the C(7) chain is parallel to [001]. The principal difference between the structure of (I) and that of (R)-histidinium (R,R)-hydrogen tartrate arises from the hydrogen-bonding characteristics of the cations. In (I) the cation is a threefold donor in N—H⋯O hydrogen bonds, whereas in (R)-histidinium (R,R)-hydrogen tartrate the cation is a fivefold donor (although not all of the N—H⋯O hydrogen bonds are listed in Table 2
of Johnson & Feeder, 2004
), and the action of the cation is to link the anion sheets into a continuous three-dimensional framework.
4. Concluding comments
For both the 1:1 salts (I)–(III) and the 2:1 salts (IV)–(VI) described here, modest changes in the stereochemical nature of the components provokes rather considerable changes in the crystallization characteristics, as manifested by a comparison of both the unit-cell dimensions and the Z′ values within each series (Table 1). At a more detailed level, no two salts described here, apart from the enantiomorphous pair (II) and (III), have a common anion and it is notable that we have not observed in any of (I)–(VI) any three-dimensional anion substructures as observed in the 1:2 salts formed by racemic tartaric acid with each of the simple achiral diamines piperazine and 1,4-diazabicycle[2.2.2]octane (Farrell et al., 2002a
). In the present series, even when the anion sub-structures are two-dimensional, the variety and the sizes of the hydrogen-bonded rings from which the sheets are built are different in every case. We have previously observed very marked diversity of supramolecular aggregation in series involving geometrical (constitutional) as opposed to setereochemical (configurational) (Bowes et al., 2003a
; Glidewell et al., 2002
, 2004
). In the salts (I) and (IV), where both components are there is no hint of any mimicry of (Figs. 11
and 15
). However, in the salts (II), (III) and (VI), where the cations are and the anions are racemic, there is strong mimicry of centrosymmetry (Figs. 12
and 14
), with weaker indications in (V) (Fig. 9
). In general, pseudo-symmetry seems to be manifest in the present series when the anions are racemic, indicating that the formation of the anion sub-structure is a major determinant of the supramolecular structure as a whole.
Supporting information
10.1107/S0108768104029684/bm5020sup1.cif
contains datablocks global, I, II, III, IV, V, VI. DOI:Structure factors: contains datablock dt08. DOI: 10.1107/S0108768104029684/bm5020Isup2.fcf
Structure factors: contains datablock inv. DOI: 10.1107/S0108768104029684/bm5020IIsup3.fcf
Structure factors: contains datablock dt16. DOI: 10.1107/S0108768104029684/bm5020IIIsup4.fcf
Structure factors: contains datablock dt19. DOI: 10.1107/S0108768104029684/bm5020IVsup5.fcf
Structure factors: contains datablock dt07. DOI: 10.1107/S0108768104029684/bm5020Vsup6.fcf
Structure factors: contains datablock dt21. DOI: 10.1107/S0108768104029684/bm5020VIsup7.fcf
For all compounds, data collection: Kappa-CCD server software (Nonius, 1997); cell
DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).C8H12N·C4H5O6 | F(000) = 288 |
Mr = 271.27 | Dx = 1.425 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 1497 reflections |
a = 6.3425 (2) Å | θ = 2.9–27.5° |
b = 13.9448 (3) Å | µ = 0.12 mm−1 |
c = 7.5021 (3) Å | T = 150 K |
β = 107.6599 (14)° | Block, colourless |
V = 632.25 (4) Å3 | 0.30 × 0.25 × 0.22 mm |
Z = 2 |
Kappa-CCD diffractometer | 1497 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 1386 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.042 |
ϕ scans, and ω scans with κ offsets | θmax = 27.5°, θmin = 2.9° |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | h = −8→7 |
Tmin = 0.923, Tmax = 0.983 | k = −17→18 |
5067 measured reflections | l = −9→9 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.077 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0419P)2 + 0.0759P] where P = (Fo2 + 2Fc2)/3 |
1497 reflections | (Δ/σ)max < 0.001 |
177 parameters | Δρmax = 0.16 e Å−3 |
1 restraint | Δρmin = −0.20 e Å−3 |
C8H12N·C4H5O6 | V = 632.25 (4) Å3 |
Mr = 271.27 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 6.3425 (2) Å | µ = 0.12 mm−1 |
b = 13.9448 (3) Å | T = 150 K |
c = 7.5021 (3) Å | 0.30 × 0.25 × 0.22 mm |
β = 107.6599 (14)° |
Kappa-CCD diffractometer | 1497 independent reflections |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | 1386 reflections with I > 2σ(I) |
Tmin = 0.923, Tmax = 0.983 | Rint = 0.042 |
5067 measured reflections |
R[F2 > 2σ(F2)] = 0.032 | 1 restraint |
wR(F2) = 0.077 | H-atom parameters constrained |
S = 1.09 | Δρmax = 0.16 e Å−3 |
1497 reflections | Δρmin = −0.20 e Å−3 |
177 parameters |
x | y | z | Uiso*/Ueq | ||
O1 | 0.2960 (2) | 0.42472 (12) | 0.49188 (18) | 0.0220 (3) | |
O2 | −0.0698 (2) | 0.42427 (12) | 0.34959 (19) | 0.0221 (3) | |
O3 | 0.2124 (2) | 0.37822 (11) | −0.21678 (19) | 0.0212 (3) | |
O4 | 0.5036 (2) | 0.47083 (12) | −0.0727 (2) | 0.0244 (3) | |
O5 | −0.0345 (2) | 0.47002 (12) | 0.02165 (18) | 0.0235 (3) | |
O6 | 0.2191 (3) | 0.29349 (10) | 0.1013 (2) | 0.0244 (3) | |
C1 | 0.1254 (3) | 0.43361 (14) | 0.3506 (2) | 0.0166 (4) | |
C2 | 0.1674 (3) | 0.46078 (15) | 0.1664 (2) | 0.0162 (4) | |
C3 | 0.3147 (3) | 0.38611 (14) | 0.1132 (3) | 0.0176 (4) | |
C4 | 0.3549 (3) | 0.41584 (14) | −0.0696 (2) | 0.0167 (4) | |
N1 | 0.7490 (3) | 0.49259 (12) | 0.6287 (2) | 0.0186 (3) | |
C11 | 0.6050 (3) | 0.64562 (14) | 0.4699 (3) | 0.0205 (4) | |
C12 | 0.6329 (4) | 0.63511 (16) | 0.2939 (3) | 0.0238 (4) | |
C13 | 0.4879 (4) | 0.67869 (17) | 0.1382 (3) | 0.0281 (5) | |
C14 | 0.3139 (4) | 0.73371 (16) | 0.1562 (4) | 0.0313 (5) | |
C15 | 0.2835 (4) | 0.74412 (17) | 0.3315 (4) | 0.0314 (5) | |
C16 | 0.4288 (4) | 0.70078 (15) | 0.4866 (3) | 0.0256 (5) | |
C17 | 0.7625 (3) | 0.60055 (15) | 0.6422 (3) | 0.0201 (4) | |
C18 | 1.0021 (4) | 0.63048 (16) | 0.6751 (3) | 0.0256 (5) | |
H3 | 0.2491 | 0.3916 | −0.3125 | 0.032* | |
H5 | −0.1403 | 0.4600 | 0.0647 | 0.035* | |
H6 | 0.1607 | 0.2789 | −0.0115 | 0.037* | |
H2 | 0.2454 | 0.5240 | 0.1836 | 0.019* | |
H3A | 0.4605 | 0.3850 | 0.2135 | 0.021* | |
H1A | 0.6047 | 0.4741 | 0.5963 | 0.028* | |
H1B | 0.8238 | 0.4665 | 0.7413 | 0.028* | |
H1C | 0.8102 | 0.4721 | 0.5403 | 0.028* | |
H12 | 0.7523 | 0.5978 | 0.2802 | 0.029* | |
H13 | 0.5082 | 0.6707 | 0.0187 | 0.034* | |
H14 | 0.2159 | 0.7642 | 0.0498 | 0.038* | |
H15 | 0.1631 | 0.7810 | 0.3446 | 0.038* | |
H16 | 0.4080 | 0.7088 | 0.6059 | 0.031* | |
H17 | 0.7172 | 0.6208 | 0.7532 | 0.024* | |
H18A | 1.0502 | 0.6107 | 0.5682 | 0.038* | |
H18B | 1.0959 | 0.5997 | 0.7891 | 0.038* | |
H18C | 1.0145 | 0.7003 | 0.6893 | 0.038* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0191 (7) | 0.0337 (7) | 0.0131 (6) | −0.0020 (6) | 0.0049 (5) | 0.0015 (6) |
O2 | 0.0191 (7) | 0.0332 (7) | 0.0165 (6) | 0.0014 (6) | 0.0091 (5) | 0.0010 (6) |
O3 | 0.0209 (7) | 0.0307 (8) | 0.0131 (6) | −0.0044 (6) | 0.0069 (5) | 0.0007 (6) |
O4 | 0.0218 (7) | 0.0331 (8) | 0.0200 (7) | −0.0061 (6) | 0.0089 (6) | −0.0010 (6) |
O5 | 0.0148 (7) | 0.0407 (8) | 0.0149 (7) | 0.0045 (6) | 0.0045 (5) | 0.0055 (6) |
O6 | 0.0350 (9) | 0.0202 (7) | 0.0205 (7) | −0.0021 (6) | 0.0120 (7) | 0.0011 (6) |
C1 | 0.0197 (9) | 0.0180 (9) | 0.0132 (8) | 0.0002 (7) | 0.0067 (7) | −0.0012 (8) |
C2 | 0.0152 (8) | 0.0213 (9) | 0.0121 (8) | −0.0001 (7) | 0.0043 (7) | 0.0017 (7) |
C3 | 0.0166 (9) | 0.0223 (9) | 0.0150 (9) | 0.0008 (8) | 0.0065 (7) | 0.0009 (8) |
C4 | 0.0150 (8) | 0.0218 (9) | 0.0140 (8) | 0.0024 (8) | 0.0053 (7) | 0.0011 (8) |
N1 | 0.0166 (8) | 0.0219 (8) | 0.0179 (8) | 0.0001 (7) | 0.0062 (6) | 0.0023 (7) |
C11 | 0.0181 (10) | 0.0183 (9) | 0.0248 (10) | −0.0015 (7) | 0.0064 (8) | 0.0010 (8) |
C12 | 0.0222 (10) | 0.0249 (10) | 0.0246 (10) | −0.0002 (8) | 0.0074 (8) | 0.0034 (8) |
C13 | 0.0289 (11) | 0.0284 (11) | 0.0241 (10) | −0.0057 (9) | 0.0038 (9) | 0.0047 (10) |
C14 | 0.0237 (11) | 0.0249 (11) | 0.0377 (12) | −0.0029 (10) | −0.0018 (9) | 0.0103 (10) |
C15 | 0.0215 (11) | 0.0227 (10) | 0.0462 (13) | 0.0045 (9) | 0.0045 (10) | 0.0012 (10) |
C16 | 0.0208 (10) | 0.0229 (11) | 0.0327 (11) | −0.0006 (8) | 0.0074 (9) | −0.0038 (9) |
C17 | 0.0205 (10) | 0.0201 (10) | 0.0203 (10) | 0.0005 (8) | 0.0070 (8) | −0.0014 (8) |
C18 | 0.0206 (10) | 0.0278 (11) | 0.0261 (10) | −0.0030 (8) | 0.0035 (8) | −0.0020 (9) |
O1—C1 | 1.270 (2) | C11—C12 | 1.392 (3) |
O2—C1 | 1.243 (2) | C11—C16 | 1.393 (3) |
O3—C4 | 1.306 (2) | C11—C17 | 1.510 (3) |
O3—H3 | 0.84 | C12—C13 | 1.389 (3) |
O4—C4 | 1.221 (2) | C12—H12 | 0.95 |
O5—C2 | 1.411 (2) | C13—C14 | 1.384 (3) |
O5—H5 | 0.84 | C13—H13 | 0.95 |
O6—C3 | 1.418 (2) | C14—C15 | 1.393 (4) |
O6—H6 | 0.84 | C14—H14 | 0.95 |
C1—C2 | 1.532 (2) | C15—C16 | 1.385 (3) |
C2—C3 | 1.531 (3) | C15—H15 | 0.95 |
C2—H2 | 1.00 | C16—H16 | 0.95 |
C3—C4 | 1.526 (3) | C17—C18 | 1.522 (3) |
C3—H3A | 1.00 | C17—H17 | 1.00 |
N1—C17 | 1.510 (3) | C18—H18A | 0.98 |
N1—H1A | 0.91 | C18—H18B | 0.98 |
N1—H1B | 0.91 | C18—H18C | 0.98 |
N1—H1C | 0.91 | ||
C4—O3—H3 | 109.5 | C16—C11—C17 | 119.55 (19) |
C2—O5—H5 | 109.5 | C13—C12—C11 | 120.6 (2) |
C3—O6—H6 | 109.5 | C13—C12—H12 | 119.7 |
O2—C1—O1 | 126.14 (17) | C11—C12—H12 | 119.7 |
O2—C1—C2 | 117.76 (16) | C14—C13—C12 | 120.3 (2) |
O1—C1—C2 | 116.08 (16) | C14—C13—H13 | 119.8 |
O5—C2—C3 | 110.16 (15) | C12—C13—H13 | 119.8 |
O5—C2—C1 | 110.55 (14) | C13—C14—C15 | 119.5 (2) |
C3—C2—C1 | 110.73 (15) | C13—C14—H14 | 120.2 |
O5—C2—H2 | 108.4 | C15—C14—H14 | 120.2 |
C3—C2—H2 | 108.4 | C16—C15—C14 | 120.0 (2) |
C1—C2—H2 | 108.4 | C16—C15—H15 | 120.0 |
O6—C3—C4 | 112.09 (16) | C14—C15—H15 | 120.0 |
O6—C3—C2 | 110.64 (15) | C15—C16—C11 | 120.9 (2) |
C4—C3—C2 | 109.33 (16) | C15—C16—H16 | 119.6 |
O6—C3—H3A | 108.2 | C11—C16—H16 | 119.6 |
C4—C3—H3A | 108.2 | N1—C17—C11 | 110.37 (16) |
C2—C3—H3A | 108.2 | N1—C17—C18 | 108.54 (17) |
O4—C4—O3 | 125.20 (17) | C11—C17—C18 | 113.16 (17) |
O4—C4—C3 | 121.87 (16) | N1—C17—H17 | 108.2 |
O3—C4—C3 | 112.91 (16) | C11—C17—H17 | 108.2 |
C17—N1—H1A | 109.5 | C18—C17—H17 | 108.2 |
C17—N1—H1B | 109.5 | C17—C18—H18A | 109.5 |
H1A—N1—H1B | 109.5 | C17—C18—H18B | 109.5 |
C17—N1—H1C | 109.5 | H18A—C18—H18B | 109.5 |
H1A—N1—H1C | 109.5 | C17—C18—H18C | 109.5 |
H1B—N1—H1C | 109.5 | H18A—C18—H18C | 109.5 |
C12—C11—C16 | 118.7 (2) | H18B—C18—H18C | 109.5 |
C12—C11—C17 | 121.78 (19) | ||
O2—C1—C2—O5 | −0.4 (3) | C16—C11—C12—C13 | 0.0 (3) |
O1—C1—C2—O5 | −178.99 (17) | C17—C11—C12—C13 | −178.87 (19) |
O2—C1—C2—C3 | −122.78 (19) | C11—C12—C13—C14 | 0.4 (3) |
O1—C1—C2—C3 | 58.6 (2) | C12—C13—C14—C15 | −0.8 (3) |
O5—C2—C3—O6 | −65.99 (19) | C13—C14—C15—C16 | 1.0 (3) |
C1—C2—C3—O6 | 56.61 (19) | C14—C15—C16—C11 | −0.7 (3) |
O5—C2—C3—C4 | 57.9 (2) | C12—C11—C16—C15 | 0.2 (3) |
C1—C2—C3—C4 | −179.47 (15) | C17—C11—C16—C15 | 179.1 (2) |
O6—C3—C4—O4 | −151.29 (18) | C12—C11—C17—N1 | −65.4 (2) |
C2—C3—C4—O4 | 85.7 (2) | C16—C11—C17—N1 | 115.74 (19) |
O6—C3—C4—O3 | 30.1 (2) | C12—C11—C17—C18 | 56.4 (3) |
C2—C3—C4—O3 | −92.9 (2) | C16—C11—C17—C18 | −122.4 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O1i | 0.84 | 1.65 | 2.486 (2) | 174 |
O5—H5···O2 | 0.84 | 2.11 | 2.616 (2) | 119 |
O5—H5···O4ii | 0.84 | 2.18 | 2.797 (2) | 130 |
O6—H6···O3 | 0.84 | 2.17 | 2.652 (2) | 116 |
N1—H1A···O1 | 0.91 | 2.00 | 2.901 (2) | 172 |
N1—H1B···O5iii | 0.91 | 2.02 | 2.867 (2) | 154 |
N1—H1C···O2iv | 0.91 | 1.93 | 2.842 (2) | 177 |
Symmetry codes: (i) x, y, z−1; (ii) x−1, y, z; (iii) x+1, y, z+1; (iv) x+1, y, z. |
C8H12N·C4H5O6 | F(000) = 576 |
Mr = 271.27 | Dx = 1.336 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 3191 reflections |
a = 7.3025 (2) Å | θ = 2.7–27.7° |
b = 22.8901 (11) Å | µ = 0.11 mm−1 |
c = 8.1193 (3) Å | T = 150 K |
β = 96.599 (2)° | Needle, colourless |
V = 1348.19 (9) Å3 | 0.28 × 0.16 × 0.14 mm |
Z = 4 |
Kappa-CCD diffractometer | 3191 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 2734 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.129 |
ϕ scans, and ω scans with κ offsets | θmax = 27.7°, θmin = 2.7° |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | h = −9→9 |
Tmin = 0.584, Tmax = 0.998 | k = −29→29 |
15852 measured reflections | l = −8→10 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.047 | H-atom parameters constrained |
wR(F2) = 0.130 | w = 1/[σ2(Fo2) + (0.0713P)2 + 0.0775P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
3191 reflections | Δρmax = 0.34 e Å−3 |
354 parameters | Δρmin = −0.24 e Å−3 |
1 restraint | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.039 (6) |
C8H12N·C4H5O6 | V = 1348.19 (9) Å3 |
Mr = 271.27 | Z = 4 |
Monoclinic, P21 | Mo Kα radiation |
a = 7.3025 (2) Å | µ = 0.11 mm−1 |
b = 22.8901 (11) Å | T = 150 K |
c = 8.1193 (3) Å | 0.28 × 0.16 × 0.14 mm |
β = 96.599 (2)° |
Kappa-CCD diffractometer | 3191 independent reflections |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | 2734 reflections with I > 2σ(I) |
Tmin = 0.584, Tmax = 0.998 | Rint = 0.129 |
15852 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | 1 restraint |
wR(F2) = 0.130 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.34 e Å−3 |
3191 reflections | Δρmin = −0.24 e Å−3 |
354 parameters |
x | y | z | Uiso*/Ueq | ||
O11 | 0.3272 (3) | 0.58482 (10) | 0.9097 (2) | 0.0363 (5) | |
O12 | 0.3593 (3) | 0.55621 (11) | 1.1755 (3) | 0.0405 (5) | |
O15 | 0.7170 (3) | 0.54608 (10) | 1.1988 (2) | 0.0366 (5) | |
O16 | 0.6239 (3) | 0.47743 (9) | 0.9105 (3) | 0.0370 (5) | |
O13 | 0.9965 (3) | 0.48977 (10) | 0.9489 (3) | 0.0381 (5) | |
O14 | 0.9756 (3) | 0.58685 (10) | 0.9130 (3) | 0.0376 (5) | |
C11 | 0.4206 (4) | 0.56938 (13) | 1.0442 (3) | 0.0326 (6) | |
C12 | 0.6307 (4) | 0.56948 (14) | 1.0461 (3) | 0.0325 (6) | |
C13 | 0.6947 (4) | 0.53480 (14) | 0.9027 (3) | 0.0331 (6) | |
C14 | 0.9063 (4) | 0.53409 (14) | 0.9225 (3) | 0.0327 (6) | |
O21 | 0.5816 (3) | 0.41528 (10) | 0.6188 (2) | 0.0351 (4) | |
O22 | 0.5502 (3) | 0.44629 (11) | 0.3542 (3) | 0.0404 (5) | |
O25 | 0.1910 (3) | 0.45112 (10) | 0.3258 (2) | 0.0373 (5) | |
O26 | 0.2844 (3) | 0.52255 (10) | 0.6151 (3) | 0.0372 (5) | |
O23 | −0.0897 (3) | 0.51062 (10) | 0.5760 (3) | 0.0385 (5) | |
O24 | −0.0679 (3) | 0.41304 (10) | 0.6051 (3) | 0.0380 (5) | |
C21 | 0.4876 (4) | 0.43169 (13) | 0.4833 (3) | 0.0334 (6) | |
C22 | 0.2775 (4) | 0.42982 (13) | 0.4803 (3) | 0.0328 (6) | |
C23 | 0.2117 (4) | 0.46514 (14) | 0.6218 (3) | 0.0334 (6) | |
C24 | 0.0007 (4) | 0.46629 (14) | 0.5987 (3) | 0.0343 (6) | |
N3 | 0.0680 (3) | 0.58651 (11) | 1.3443 (3) | 0.0333 (5) | |
C31 | 0.1949 (4) | 0.68531 (14) | 1.4188 (4) | 0.0384 (6) | |
C32 | 0.2889 (5) | 0.67206 (15) | 1.5730 (4) | 0.0436 (7) | |
C33 | 0.4374 (5) | 0.70634 (17) | 1.6392 (5) | 0.0505 (8) | |
C34 | 0.4901 (5) | 0.75446 (17) | 1.5522 (5) | 0.0522 (9) | |
C35 | 0.3969 (5) | 0.76803 (17) | 1.3991 (5) | 0.0543 (9) | |
C36 | 0.2503 (5) | 0.73294 (16) | 1.3315 (4) | 0.0482 (8) | |
C37 | 0.0260 (4) | 0.65053 (14) | 1.3515 (4) | 0.0388 (6) | |
C38 | −0.1344 (5) | 0.65949 (17) | 1.4535 (5) | 0.0520 (8) | |
N4 | 0.8388 (3) | 0.41354 (11) | 0.1841 (3) | 0.0341 (5) | |
C41 | 0.9610 (4) | 0.31838 (14) | 0.0957 (4) | 0.0371 (6) | |
C42 | 1.0452 (5) | 0.34204 (15) | −0.0339 (4) | 0.0424 (7) | |
C43 | 1.1758 (5) | 0.31047 (16) | −0.1084 (4) | 0.0468 (7) | |
C44 | 1.2232 (4) | 0.25444 (15) | −0.0543 (4) | 0.0449 (7) | |
C45 | 1.1391 (5) | 0.23028 (16) | 0.0749 (5) | 0.0481 (8) | |
C46 | 1.0097 (5) | 0.26189 (15) | 0.1493 (4) | 0.0447 (7) | |
C47 | 0.8086 (4) | 0.34888 (13) | 0.1724 (4) | 0.0360 (6) | |
C48 | 0.6201 (4) | 0.33761 (17) | 0.0746 (4) | 0.0468 (7) | |
H15 | 0.6358 | 0.5343 | 1.2562 | 0.055* | |
H16 | 0.6220 | 0.4614 | 0.8173 | 0.056* | |
H14 | 1.0907 | 0.5846 | 0.9157 | 0.056* | |
H15A | 0.6722 | 0.6109 | 1.0369 | 0.039* | |
H16A | 0.6470 | 0.5534 | 0.7947 | 0.040* | |
H25 | 0.2716 | 0.4636 | 0.2688 | 0.056* | |
H26 | 0.2899 | 0.5380 | 0.7094 | 0.056* | |
H24 | −0.1818 | 0.4151 | 0.6112 | 0.057* | |
H25A | 0.2395 | 0.3882 | 0.4926 | 0.039* | |
H26A | 0.2568 | 0.4466 | 0.7305 | 0.040* | |
H3A | 0.1576 | 0.5806 | 1.2770 | 0.050* | |
H3B | −0.0357 | 0.5668 | 1.3036 | 0.050* | |
H3C | 0.1074 | 0.5733 | 1.4481 | 0.050* | |
H32 | 0.2518 | 0.6395 | 1.6336 | 0.052* | |
H33 | 0.5023 | 0.6967 | 1.7439 | 0.061* | |
H34 | 0.5902 | 0.7781 | 1.5978 | 0.063* | |
H35 | 0.4323 | 0.8012 | 1.3398 | 0.065* | |
H36 | 0.1885 | 0.7418 | 1.2250 | 0.058* | |
H37 | −0.0137 | 0.6643 | 1.2360 | 0.047* | |
H38A | −0.0988 | 0.6461 | 1.5673 | 0.078* | |
H38B | −0.2412 | 0.6371 | 1.4042 | 0.078* | |
H38C | −0.1662 | 0.7011 | 1.4545 | 0.078* | |
H4A | 0.7620 | 0.4293 | 0.2529 | 0.051* | |
H4B | 0.9579 | 0.4209 | 0.2250 | 0.051* | |
H4C | 0.8148 | 0.4298 | 0.0816 | 0.051* | |
H42 | 1.0131 | 0.3803 | −0.0721 | 0.051* | |
H43 | 1.2327 | 0.3273 | −0.1965 | 0.056* | |
H44 | 1.3124 | 0.2328 | −0.1051 | 0.054* | |
H45 | 1.1706 | 0.1919 | 0.1122 | 0.058* | |
H46 | 0.9534 | 0.2450 | 0.2378 | 0.054* | |
H47 | 0.8062 | 0.3333 | 0.2872 | 0.043* | |
H48A | 0.6179 | 0.3540 | −0.0371 | 0.070* | |
H48B | 0.5239 | 0.3562 | 0.1314 | 0.070* | |
H48C | 0.5976 | 0.2954 | 0.0669 | 0.070* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O11 | 0.0331 (10) | 0.0418 (12) | 0.0339 (10) | 0.0007 (9) | 0.0033 (8) | 0.0017 (8) |
O12 | 0.0357 (10) | 0.0512 (13) | 0.0359 (11) | 0.0044 (10) | 0.0097 (9) | 0.0043 (9) |
O15 | 0.0335 (10) | 0.0484 (13) | 0.0277 (9) | −0.0021 (9) | 0.0026 (7) | 0.0015 (9) |
O16 | 0.0399 (10) | 0.0381 (11) | 0.0331 (10) | −0.0056 (9) | 0.0041 (8) | −0.0042 (8) |
O13 | 0.0392 (10) | 0.0381 (12) | 0.0372 (11) | 0.0030 (9) | 0.0058 (9) | 0.0026 (9) |
O14 | 0.0302 (9) | 0.0380 (11) | 0.0455 (12) | 0.0007 (8) | 0.0072 (8) | 0.0010 (9) |
C11 | 0.0301 (13) | 0.0343 (14) | 0.0339 (14) | −0.0012 (11) | 0.0062 (11) | −0.0017 (11) |
C12 | 0.0307 (13) | 0.0371 (15) | 0.0296 (13) | −0.0009 (11) | 0.0037 (10) | 0.0001 (11) |
C13 | 0.0341 (14) | 0.0346 (14) | 0.0309 (13) | −0.0004 (12) | 0.0048 (10) | 0.0015 (11) |
C14 | 0.0333 (13) | 0.0362 (15) | 0.0290 (13) | −0.0003 (12) | 0.0061 (10) | 0.0014 (11) |
O21 | 0.0320 (9) | 0.0398 (11) | 0.0332 (10) | 0.0021 (9) | 0.0027 (7) | 0.0014 (9) |
O22 | 0.0350 (10) | 0.0523 (14) | 0.0345 (11) | 0.0021 (9) | 0.0074 (8) | 0.0028 (9) |
O25 | 0.0329 (10) | 0.0497 (13) | 0.0292 (10) | −0.0014 (9) | 0.0027 (8) | 0.0011 (9) |
O26 | 0.0404 (11) | 0.0390 (12) | 0.0320 (10) | −0.0020 (9) | 0.0032 (8) | −0.0037 (8) |
O23 | 0.0359 (11) | 0.0417 (12) | 0.0383 (11) | 0.0055 (9) | 0.0064 (8) | 0.0053 (9) |
O24 | 0.0327 (9) | 0.0403 (11) | 0.0419 (11) | −0.0006 (9) | 0.0079 (8) | 0.0005 (9) |
C21 | 0.0340 (13) | 0.0338 (15) | 0.0328 (13) | −0.0005 (11) | 0.0056 (11) | −0.0020 (11) |
C22 | 0.0327 (13) | 0.0371 (15) | 0.0287 (13) | 0.0003 (12) | 0.0034 (10) | 0.0008 (11) |
C23 | 0.0336 (13) | 0.0353 (15) | 0.0317 (14) | 0.0011 (12) | 0.0047 (10) | 0.0010 (11) |
C24 | 0.0345 (13) | 0.0431 (17) | 0.0255 (12) | 0.0028 (13) | 0.0047 (10) | 0.0003 (11) |
N3 | 0.0349 (11) | 0.0340 (12) | 0.0313 (12) | 0.0002 (10) | 0.0050 (9) | −0.0016 (9) |
C31 | 0.0419 (15) | 0.0354 (15) | 0.0376 (15) | −0.0012 (13) | 0.0033 (12) | −0.0001 (12) |
C32 | 0.0501 (17) | 0.0399 (16) | 0.0393 (15) | −0.0043 (14) | −0.0008 (13) | −0.0006 (12) |
C33 | 0.0502 (18) | 0.0503 (19) | 0.0479 (18) | −0.0006 (16) | −0.0071 (15) | −0.0070 (15) |
C34 | 0.0442 (17) | 0.0463 (19) | 0.065 (2) | −0.0059 (15) | 0.0036 (16) | −0.0136 (17) |
C35 | 0.059 (2) | 0.0423 (19) | 0.062 (2) | −0.0085 (16) | 0.0104 (17) | 0.0048 (16) |
C36 | 0.0549 (19) | 0.0431 (17) | 0.0455 (17) | −0.0015 (15) | 0.0017 (14) | 0.0058 (14) |
C37 | 0.0411 (15) | 0.0351 (15) | 0.0394 (15) | 0.0025 (13) | 0.0002 (12) | −0.0002 (12) |
C38 | 0.0434 (17) | 0.052 (2) | 0.061 (2) | 0.0027 (15) | 0.0078 (15) | −0.0162 (17) |
N4 | 0.0330 (11) | 0.0373 (13) | 0.0322 (11) | −0.0003 (11) | 0.0039 (9) | −0.0013 (10) |
C41 | 0.0403 (15) | 0.0388 (15) | 0.0311 (13) | −0.0003 (13) | 0.0000 (11) | 0.0001 (11) |
C42 | 0.0485 (17) | 0.0374 (15) | 0.0421 (15) | 0.0039 (14) | 0.0092 (13) | 0.0028 (13) |
C43 | 0.0508 (18) | 0.0464 (18) | 0.0438 (17) | 0.0001 (15) | 0.0079 (14) | −0.0027 (14) |
C44 | 0.0377 (15) | 0.0417 (16) | 0.0543 (18) | 0.0028 (13) | 0.0014 (13) | −0.0115 (14) |
C45 | 0.0452 (17) | 0.0372 (16) | 0.060 (2) | 0.0023 (14) | −0.0021 (15) | −0.0020 (15) |
C46 | 0.0492 (18) | 0.0386 (17) | 0.0452 (17) | −0.0003 (14) | 0.0009 (14) | 0.0053 (13) |
C47 | 0.0380 (14) | 0.0336 (15) | 0.0362 (14) | −0.0025 (12) | 0.0038 (11) | 0.0025 (11) |
C48 | 0.0384 (16) | 0.0478 (19) | 0.0536 (18) | −0.0045 (14) | 0.0027 (13) | −0.0076 (15) |
O11—C11 | 1.269 (4) | C32—C33 | 1.395 (5) |
O12—C11 | 1.240 (3) | C32—H32 | 0.95 |
O15—C12 | 1.428 (3) | C33—C34 | 1.387 (6) |
O15—H15 | 0.84 | C33—H33 | 0.95 |
O16—C13 | 1.415 (4) | C34—C35 | 1.382 (6) |
O16—H16 | 0.84 | C34—H34 | 0.95 |
O13—C14 | 1.215 (4) | C35—C36 | 1.399 (5) |
O14—C14 | 1.315 (4) | C35—H35 | 0.95 |
O14—H14 | 0.84 | C36—H36 | 0.95 |
C11—C12 | 1.533 (4) | C37—C38 | 1.523 (5) |
C12—C13 | 1.527 (4) | C37—H37 | 1.00 |
C12—H15A | 1.00 | C38—H38A | 0.98 |
C13—C14 | 1.535 (4) | C38—H38B | 0.98 |
C13—H16A | 1.00 | C38—H38C | 0.98 |
O21—C21 | 1.284 (4) | N4—C47 | 1.498 (4) |
O22—C21 | 1.237 (4) | N4—H4A | 0.91 |
O25—C22 | 1.424 (3) | N4—H4B | 0.91 |
O25—H25 | 0.84 | N4—H4C | 0.91 |
O26—C23 | 1.421 (4) | C41—C42 | 1.388 (4) |
O26—H26 | 0.84 | C41—C46 | 1.397 (5) |
O23—C24 | 1.213 (4) | C41—C47 | 1.508 (4) |
O24—C24 | 1.321 (4) | C42—C43 | 1.389 (5) |
O24—H24 | 0.84 | C42—H42 | 0.95 |
C21—C22 | 1.532 (4) | C43—C44 | 1.386 (5) |
C22—C23 | 1.527 (4) | C43—H43 | 0.95 |
C22—H25A | 1.00 | C44—C45 | 1.390 (5) |
C23—C24 | 1.531 (4) | C44—H44 | 0.95 |
C23—H26A | 1.00 | C45—C46 | 1.383 (5) |
N3—C37 | 1.500 (4) | C45—H45 | 0.95 |
N3—H3A | 0.91 | C46—H46 | 0.95 |
N3—H3B | 0.91 | C47—C48 | 1.530 (4) |
N3—H3C | 0.91 | C47—H47 | 1.00 |
C31—C36 | 1.386 (5) | C48—H48A | 0.98 |
C31—C32 | 1.390 (4) | C48—H48B | 0.98 |
C31—C37 | 1.516 (4) | C48—H48C | 0.98 |
C12—O15—H15 | 109.5 | C35—C34—C33 | 120.0 (3) |
C13—O16—H16 | 109.5 | C35—C34—H34 | 120.0 |
C14—O14—H14 | 109.5 | C33—C34—H34 | 120.0 |
O12—C11—O11 | 126.6 (3) | C34—C35—C36 | 120.0 (3) |
O12—C11—C12 | 116.8 (2) | C34—C35—H35 | 120.0 |
O11—C11—C12 | 116.5 (2) | C36—C35—H35 | 120.0 |
O15—C12—C13 | 108.9 (2) | C31—C36—C35 | 120.4 (3) |
O15—C12—C11 | 110.5 (2) | C31—C36—H36 | 119.8 |
C13—C12—C11 | 112.7 (2) | C35—C36—H36 | 119.8 |
O15—C12—H15A | 108.2 | N3—C37—C31 | 111.5 (2) |
C13—C12—H15A | 108.2 | N3—C37—C38 | 109.0 (3) |
C11—C12—H15A | 108.2 | C31—C37—C38 | 112.2 (3) |
O16—C13—C12 | 107.6 (2) | N3—C37—H37 | 108.0 |
O16—C13—C14 | 110.7 (2) | C31—C37—H37 | 108.0 |
C12—C13—C14 | 108.6 (2) | C38—C37—H37 | 108.0 |
O16—C13—H16A | 110.0 | C37—C38—H38A | 109.5 |
C12—C13—H16A | 110.0 | C37—C38—H38B | 109.5 |
C14—C13—H16A | 110.0 | H38A—C38—H38B | 109.5 |
O13—C14—O14 | 124.9 (3) | C37—C38—H38C | 109.5 |
O13—C14—C13 | 123.1 (3) | H38A—C38—H38C | 109.5 |
O14—C14—C13 | 112.0 (2) | H38B—C38—H38C | 109.5 |
C22—O25—H25 | 109.5 | C47—N4—H4A | 109.5 |
C23—O26—H26 | 109.5 | C47—N4—H4B | 109.5 |
C24—O24—H24 | 109.5 | H4A—N4—H4B | 109.5 |
O22—C21—O21 | 126.3 (3) | C47—N4—H4C | 109.5 |
O22—C21—C22 | 117.5 (3) | H4A—N4—H4C | 109.5 |
O21—C21—C22 | 116.2 (2) | H4B—N4—H4C | 109.5 |
O25—C22—C23 | 109.6 (2) | C42—C41—C46 | 118.6 (3) |
O25—C22—C21 | 110.3 (2) | C42—C41—C47 | 123.0 (3) |
C23—C22—C21 | 112.0 (2) | C46—C41—C47 | 118.3 (3) |
O25—C22—H25A | 108.3 | C41—C42—C43 | 120.9 (3) |
C23—C22—H25A | 108.3 | C41—C42—H42 | 119.6 |
C21—C22—H25A | 108.3 | C43—C42—H42 | 119.6 |
O26—C23—C22 | 108.0 (2) | C44—C43—C42 | 120.1 (3) |
O26—C23—C24 | 110.8 (2) | C44—C43—H43 | 119.9 |
C22—C23—C24 | 108.4 (2) | C42—C43—H43 | 119.9 |
O26—C23—H26A | 109.9 | C43—C44—C45 | 119.4 (3) |
C22—C23—H26A | 109.9 | C43—C44—H44 | 120.3 |
C24—C23—H26A | 109.9 | C45—C44—H44 | 120.3 |
O23—C24—O24 | 125.2 (3) | C46—C45—C44 | 120.3 (3) |
O23—C24—C23 | 123.7 (3) | C46—C45—H45 | 119.8 |
O24—C24—C23 | 111.1 (2) | C44—C45—H45 | 119.8 |
C37—N3—H3A | 109.5 | C45—C46—C41 | 120.7 (3) |
C37—N3—H3B | 109.5 | C45—C46—H46 | 119.7 |
H3A—N3—H3B | 109.5 | C41—C46—H46 | 119.7 |
C37—N3—H3C | 109.5 | N4—C47—C41 | 111.9 (2) |
H3A—N3—H3C | 109.5 | N4—C47—C48 | 108.5 (2) |
H3B—N3—H3C | 109.5 | C41—C47—C48 | 111.7 (3) |
C36—C31—C32 | 119.3 (3) | N4—C47—H47 | 108.2 |
C36—C31—C37 | 120.1 (3) | C41—C47—H47 | 108.2 |
C32—C31—C37 | 120.5 (3) | C48—C47—H47 | 108.2 |
C31—C32—C33 | 120.4 (3) | C47—C48—H48A | 109.5 |
C31—C32—H32 | 119.8 | C47—C48—H48B | 109.5 |
C33—C32—H32 | 119.8 | H48A—C48—H48B | 109.5 |
C34—C33—C32 | 119.9 (3) | C47—C48—H48C | 109.5 |
C34—C33—H33 | 120.0 | H48A—C48—H48C | 109.5 |
C32—C33—H33 | 120.0 | H48B—C48—H48C | 109.5 |
O12—C11—C12—O15 | 7.9 (4) | C36—C31—C32—C33 | 0.1 (5) |
O11—C11—C12—O15 | −174.6 (3) | C37—C31—C32—C33 | −176.0 (3) |
O12—C11—C12—C13 | 129.9 (3) | C31—C32—C33—C34 | 1.0 (6) |
O11—C11—C12—C13 | −52.5 (4) | C32—C33—C34—C35 | −0.7 (6) |
O15—C12—C13—O16 | 66.6 (3) | C33—C34—C35—C36 | −0.5 (6) |
C11—C12—C13—O16 | −56.3 (3) | C32—C31—C36—C35 | −1.3 (5) |
O15—C12—C13—C14 | −53.3 (3) | C37—C31—C36—C35 | 174.8 (3) |
C11—C12—C13—C14 | −176.2 (2) | C34—C35—C36—C31 | 1.5 (6) |
O16—C13—C14—O13 | −3.1 (4) | C36—C31—C37—N3 | 127.7 (3) |
C12—C13—C14—O13 | 114.8 (3) | C32—C31—C37—N3 | −56.3 (4) |
O16—C13—C14—O14 | 179.0 (2) | C36—C31—C37—C38 | −109.7 (4) |
C12—C13—C14—O14 | −63.1 (3) | C32—C31—C37—C38 | 66.3 (4) |
O22—C21—C22—O25 | −5.2 (4) | C46—C41—C42—C43 | −0.3 (5) |
O21—C21—C22—O25 | 177.8 (3) | C47—C41—C42—C43 | −175.3 (3) |
O22—C21—C22—C23 | −127.5 (3) | C41—C42—C43—C44 | 0.3 (5) |
O21—C21—C22—C23 | 55.5 (3) | C42—C43—C44—C45 | 0.0 (5) |
O25—C22—C23—O26 | −68.8 (3) | C43—C44—C45—C46 | −0.2 (5) |
C21—C22—C23—O26 | 54.0 (3) | C44—C45—C46—C41 | 0.2 (5) |
O25—C22—C23—C24 | 51.3 (3) | C42—C41—C46—C45 | 0.0 (5) |
C21—C22—C23—C24 | 174.1 (2) | C47—C41—C46—C45 | 175.3 (3) |
O26—C23—C24—O23 | 0.8 (4) | C42—C41—C47—N4 | −37.7 (4) |
C22—C23—C24—O23 | −117.6 (3) | C46—C41—C47—N4 | 147.3 (3) |
O26—C23—C24—O24 | −179.9 (2) | C42—C41—C47—C48 | 84.2 (4) |
C22—C23—C24—O24 | 61.7 (3) | C46—C41—C47—C48 | −90.8 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O15—H15···O12 | 0.84 | 2.11 | 2.607 (3) | 118 |
O15—H15···O22i | 0.84 | 2.28 | 2.941 (3) | 136 |
O16—H16···O21 | 0.84 | 1.92 | 2.750 (3) | 169 |
O14—H14···O11ii | 0.84 | 1.73 | 2.571 (3) | 175 |
O25—H25···O22 | 0.84 | 2.11 | 2.610 (3) | 118 |
O25—H25···O12iii | 0.84 | 2.36 | 3.022 (3) | 136 |
O26—H26···O11 | 0.84 | 1.94 | 2.771 (3) | 170 |
O24—H24···O21iv | 0.84 | 1.74 | 2.576 (3) | 177 |
N3—H3A···O12 | 0.91 | 1.85 | 2.749 (3) | 167 |
N3—H3B···O15iv | 0.91 | 1.96 | 2.850 (3) | 164 |
N3—H3C···O26i | 0.91 | 2.11 | 2.945 (3) | 152 |
N3—H3C···O23i | 0.91 | 2.36 | 2.894 (3) | 118 |
N4—H4A···O22 | 0.91 | 1.87 | 2.753 (3) | 162 |
N4—H4B···O25ii | 0.91 | 1.93 | 2.828 (3) | 169 |
N4—H4C···O16iii | 0.91 | 2.15 | 2.956 (3) | 147 |
N4—H4C···O13iii | 0.91 | 2.27 | 2.919 (3) | 128 |
Symmetry codes: (i) x, y, z+1; (ii) x+1, y, z; (iii) x, y, z−1; (iv) x−1, y, z. |
C8H12N·C4H5O6 | F(000) = 576 |
Mr = 271.27 | Dx = 1.339 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 9403 reflections |
a = 7.2952 (2) Å | θ = 2.7–27.5° |
b = 22.8935 (11) Å | µ = 0.11 mm−1 |
c = 8.1100 (3) Å | T = 150 K |
β = 96.603 (2)° | Block, colourless |
V = 1345.49 (9) Å3 | 0.36 × 0.26 × 0.20 mm |
Z = 4 |
Kappa-CCD diffractometer | 3160 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 2446 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.061 |
ϕ scans, and ω scans with κ offsets | θmax = 27.5°, θmin = 2.7° |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | h = −9→9 |
Tmin = 0.869, Tmax = 0.991 | k = −27→29 |
9403 measured reflections | l = −9→10 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.040 | H-atom parameters constrained |
wR(F2) = 0.091 | w = 1/[σ2(Fo2) + (0.0449P)2 + 0.0771P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
3160 reflections | Δρmax = 0.18 e Å−3 |
354 parameters | Δρmin = −0.21 e Å−3 |
1 restraint | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.020 (3) |
C8H12N·C4H5O6 | V = 1345.49 (9) Å3 |
Mr = 271.27 | Z = 4 |
Monoclinic, P21 | Mo Kα radiation |
a = 7.2952 (2) Å | µ = 0.11 mm−1 |
b = 22.8935 (11) Å | T = 150 K |
c = 8.1100 (3) Å | 0.36 × 0.26 × 0.20 mm |
β = 96.603 (2)° |
Kappa-CCD diffractometer | 3160 independent reflections |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | 2446 reflections with I > 2σ(I) |
Tmin = 0.869, Tmax = 0.991 | Rint = 0.061 |
9403 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 1 restraint |
wR(F2) = 0.091 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.18 e Å−3 |
3160 reflections | Δρmin = −0.21 e Å−3 |
354 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
O11 | 0.3272 (2) | 0.41530 (9) | 0.9097 (2) | 0.0257 (5) | |
O12 | 0.3595 (2) | 0.44399 (9) | 1.1757 (2) | 0.0288 (5) | |
O13 | 0.9959 (2) | 0.51043 (9) | 0.9486 (2) | 0.0270 (5) | |
O14 | 0.9757 (2) | 0.41304 (9) | 0.9131 (3) | 0.0271 (5) | |
H14 | 1.0908 | 0.4153 | 0.9147 | 0.041* | |
O15 | 0.7173 (2) | 0.45378 (9) | 1.1989 (2) | 0.0252 (5) | |
H15 | 0.6373 | 0.4698 | 1.2505 | 0.038* | |
O16 | 0.6238 (3) | 0.52254 (8) | 0.9103 (2) | 0.0253 (4) | |
H16 | 0.6153 | 0.5378 | 0.8156 | 0.038* | |
C11 | 0.4202 (3) | 0.43080 (12) | 1.0439 (3) | 0.0212 (6) | |
C12 | 0.6310 (3) | 0.43043 (13) | 1.0460 (3) | 0.0220 (6) | |
H12A | 0.6724 | 0.3890 | 1.0365 | 0.026* | |
C13 | 0.6952 (3) | 0.46536 (13) | 0.9026 (3) | 0.0207 (6) | |
H13A | 0.6475 | 0.4468 | 0.7944 | 0.025* | |
C14 | 0.9061 (3) | 0.46575 (13) | 0.9224 (3) | 0.0218 (6) | |
O21 | 0.5810 (2) | 0.58454 (9) | 0.6180 (2) | 0.0248 (4) | |
O22 | 0.5501 (2) | 0.55369 (9) | 0.3546 (2) | 0.0299 (5) | |
O23 | −0.0889 (3) | 0.48931 (9) | 0.5760 (2) | 0.0275 (5) | |
O24 | −0.0681 (2) | 0.58693 (9) | 0.6050 (2) | 0.0269 (5) | |
H24 | −0.1826 | 0.5849 | 0.6083 | 0.040* | |
O25 | 0.1912 (2) | 0.54904 (9) | 0.3256 (2) | 0.0267 (5) | |
H25 | 0.2717 | 0.5361 | 0.2690 | 0.040* | |
O26 | 0.2846 (3) | 0.47761 (9) | 0.6146 (2) | 0.0258 (5) | |
H26 | 0.2974 | 0.4632 | 0.7104 | 0.039* | |
C21 | 0.4874 (3) | 0.56854 (12) | 0.4839 (3) | 0.0223 (6) | |
C22 | 0.2775 (3) | 0.56993 (13) | 0.4797 (3) | 0.0226 (6) | |
H22A | 0.2390 | 0.6115 | 0.4922 | 0.027* | |
C23 | 0.2120 (3) | 0.53486 (13) | 0.6208 (3) | 0.0220 (6) | |
H23A | 0.2577 | 0.5534 | 0.7294 | 0.026* | |
C24 | 0.0006 (3) | 0.53375 (13) | 0.5993 (3) | 0.0217 (6) | |
N3 | 0.0681 (3) | 0.41331 (10) | 1.3442 (3) | 0.0231 (5) | |
H3A | 0.1070 | 0.4266 | 1.4481 | 0.035* | |
H3B | −0.0357 | 0.4329 | 1.3029 | 0.035* | |
H3C | 0.1582 | 0.4193 | 1.2772 | 0.035* | |
C31 | 0.1950 (4) | 0.31489 (13) | 1.4185 (4) | 0.0260 (6) | |
C32 | 0.2900 (4) | 0.32782 (14) | 1.5730 (4) | 0.0333 (7) | |
H32 | 0.2536 | 0.3604 | 1.6341 | 0.040* | |
C33 | 0.4377 (4) | 0.29348 (15) | 1.6387 (4) | 0.0391 (8) | |
H33 | 0.5028 | 0.3030 | 1.7435 | 0.047* | |
C34 | 0.4897 (4) | 0.24573 (15) | 1.5519 (4) | 0.0418 (8) | |
H34 | 0.5898 | 0.2220 | 1.5975 | 0.050* | |
C35 | 0.3967 (4) | 0.23222 (16) | 1.3988 (5) | 0.0437 (8) | |
H35 | 0.4326 | 0.1992 | 1.3391 | 0.052* | |
C36 | 0.2505 (4) | 0.26695 (14) | 1.3321 (4) | 0.0368 (7) | |
H36 | 0.1877 | 0.2578 | 1.2260 | 0.044* | |
C37 | 0.0268 (4) | 0.34927 (13) | 1.3516 (4) | 0.0278 (7) | |
H37 | −0.0127 | 0.3355 | 1.2359 | 0.033* | |
C38 | −0.1340 (4) | 0.34033 (16) | 1.4533 (5) | 0.0421 (8) | |
H38A | −0.1012 | 0.3557 | 1.5655 | 0.063* | |
H38B | −0.1614 | 0.2985 | 1.4595 | 0.063* | |
H38C | −0.2429 | 0.3610 | 1.4002 | 0.063* | |
N4 | 0.8388 (3) | 0.58646 (10) | 0.1844 (3) | 0.0236 (5) | |
H4A | 0.8162 | 0.5702 | 0.0817 | 0.035* | |
H4B | 0.9578 | 0.5793 | 0.2263 | 0.035* | |
H4C | 0.7614 | 0.5706 | 0.2526 | 0.035* | |
C41 | 0.9609 (4) | 0.68175 (13) | 0.0957 (3) | 0.0265 (6) | |
C42 | 1.0442 (4) | 0.65797 (14) | −0.0343 (4) | 0.0320 (7) | |
H42 | 1.0115 | 0.6198 | −0.0729 | 0.038* | |
C43 | 1.1751 (4) | 0.68962 (14) | −0.1082 (4) | 0.0361 (7) | |
H43 | 1.2324 | 0.6728 | −0.1963 | 0.043* | |
C44 | 1.2225 (4) | 0.74541 (14) | −0.0546 (4) | 0.0358 (7) | |
H44 | 1.3118 | 0.7670 | −0.1056 | 0.043* | |
C45 | 1.1386 (4) | 0.76969 (14) | 0.0745 (4) | 0.0377 (8) | |
H45 | 1.1699 | 0.8082 | 0.1116 | 0.045* | |
C46 | 1.0098 (4) | 0.73805 (14) | 0.1490 (4) | 0.0339 (7) | |
H46 | 0.9538 | 0.7549 | 0.2379 | 0.041* | |
C47 | 0.8077 (4) | 0.65096 (12) | 0.1724 (4) | 0.0251 (6) | |
H47 | 0.8050 | 0.6666 | 0.2872 | 0.030* | |
C48 | 0.6202 (4) | 0.66221 (15) | 0.0749 (4) | 0.0385 (8) | |
H48A | 0.6197 | 0.6472 | −0.0383 | 0.058* | |
H48B | 0.5956 | 0.7043 | 0.0710 | 0.058* | |
H48C | 0.5243 | 0.6424 | 0.1292 | 0.058* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O11 | 0.0198 (9) | 0.0312 (12) | 0.0260 (11) | −0.0019 (8) | 0.0028 (8) | −0.0015 (9) |
O12 | 0.0220 (9) | 0.0377 (13) | 0.0277 (11) | −0.0034 (9) | 0.0069 (9) | −0.0032 (9) |
O13 | 0.0250 (10) | 0.0287 (12) | 0.0279 (11) | −0.0042 (9) | 0.0060 (9) | −0.0041 (9) |
O14 | 0.0161 (8) | 0.0259 (11) | 0.0400 (12) | −0.0009 (8) | 0.0057 (8) | −0.0003 (9) |
O15 | 0.0176 (9) | 0.0360 (13) | 0.0218 (10) | 0.0031 (8) | 0.0011 (8) | 0.0001 (9) |
O16 | 0.0267 (10) | 0.0280 (11) | 0.0208 (10) | 0.0042 (8) | 0.0022 (8) | 0.0027 (8) |
C11 | 0.0184 (12) | 0.0225 (15) | 0.0228 (15) | 0.0003 (11) | 0.0030 (11) | 0.0024 (12) |
C12 | 0.0164 (12) | 0.0261 (16) | 0.0232 (14) | 0.0020 (11) | 0.0014 (11) | −0.0015 (12) |
C13 | 0.0185 (12) | 0.0224 (15) | 0.0212 (14) | 0.0007 (11) | 0.0026 (11) | −0.0010 (11) |
C14 | 0.0239 (14) | 0.0246 (16) | 0.0175 (13) | −0.0018 (13) | 0.0049 (11) | −0.0016 (12) |
O21 | 0.0199 (9) | 0.0272 (11) | 0.0271 (10) | −0.0015 (8) | 0.0010 (8) | −0.0016 (9) |
O22 | 0.0210 (10) | 0.0406 (13) | 0.0290 (11) | −0.0026 (9) | 0.0066 (8) | −0.0010 (9) |
O23 | 0.0234 (10) | 0.0291 (12) | 0.0304 (11) | −0.0054 (8) | 0.0046 (8) | −0.0056 (9) |
O24 | 0.0175 (9) | 0.0287 (12) | 0.0349 (11) | −0.0009 (9) | 0.0050 (8) | −0.0017 (9) |
O25 | 0.0202 (9) | 0.0386 (13) | 0.0210 (10) | 0.0008 (9) | 0.0012 (8) | −0.0001 (9) |
O26 | 0.0258 (10) | 0.0263 (12) | 0.0251 (10) | 0.0022 (8) | 0.0017 (8) | 0.0039 (8) |
C21 | 0.0201 (13) | 0.0215 (16) | 0.0251 (15) | −0.0010 (11) | 0.0015 (12) | 0.0044 (12) |
C22 | 0.0191 (12) | 0.0265 (16) | 0.0223 (14) | −0.0009 (12) | 0.0028 (11) | −0.0004 (12) |
C23 | 0.0204 (13) | 0.0230 (15) | 0.0224 (14) | 0.0001 (11) | 0.0019 (11) | −0.0001 (12) |
C24 | 0.0200 (13) | 0.0282 (17) | 0.0175 (13) | −0.0009 (12) | 0.0048 (11) | 0.0007 (12) |
N3 | 0.0214 (11) | 0.0263 (13) | 0.0212 (12) | −0.0002 (10) | 0.0015 (9) | 0.0023 (10) |
C31 | 0.0246 (13) | 0.0241 (16) | 0.0293 (15) | −0.0010 (12) | 0.0026 (12) | 0.0018 (12) |
C32 | 0.0345 (15) | 0.0318 (18) | 0.0326 (17) | 0.0030 (13) | −0.0008 (13) | −0.0028 (13) |
C33 | 0.0381 (17) | 0.036 (2) | 0.0412 (18) | −0.0017 (15) | −0.0048 (15) | 0.0066 (16) |
C34 | 0.0304 (16) | 0.036 (2) | 0.058 (2) | 0.0059 (14) | 0.0029 (16) | 0.0144 (17) |
C35 | 0.0435 (19) | 0.0331 (19) | 0.056 (2) | 0.0064 (15) | 0.0107 (17) | −0.0014 (16) |
C36 | 0.0414 (18) | 0.0315 (18) | 0.0365 (17) | −0.0011 (14) | 0.0006 (14) | −0.0038 (14) |
C37 | 0.0258 (14) | 0.0254 (16) | 0.0314 (16) | −0.0059 (13) | −0.0003 (12) | −0.0002 (13) |
C38 | 0.0283 (15) | 0.041 (2) | 0.057 (2) | 0.0001 (14) | 0.0082 (15) | 0.0193 (17) |
N4 | 0.0211 (11) | 0.0274 (14) | 0.0224 (12) | 0.0001 (10) | 0.0034 (9) | 0.0006 (10) |
C41 | 0.0246 (14) | 0.0259 (16) | 0.0279 (15) | 0.0014 (12) | −0.0022 (12) | 0.0008 (12) |
C42 | 0.0354 (16) | 0.0258 (16) | 0.0350 (16) | −0.0032 (13) | 0.0051 (13) | −0.0009 (13) |
C43 | 0.0375 (17) | 0.0327 (19) | 0.0390 (18) | 0.0010 (14) | 0.0086 (14) | 0.0036 (14) |
C44 | 0.0261 (15) | 0.0317 (18) | 0.0485 (19) | −0.0008 (13) | −0.0011 (14) | 0.0130 (16) |
C45 | 0.0328 (16) | 0.0239 (17) | 0.054 (2) | −0.0011 (13) | −0.0055 (15) | 0.0020 (15) |
C46 | 0.0327 (16) | 0.0289 (18) | 0.0387 (17) | 0.0021 (13) | −0.0019 (14) | −0.0044 (14) |
C47 | 0.0246 (14) | 0.0226 (15) | 0.0279 (15) | 0.0035 (12) | 0.0017 (12) | −0.0032 (12) |
C48 | 0.0285 (15) | 0.0363 (19) | 0.050 (2) | 0.0070 (14) | 0.0024 (14) | 0.0063 (16) |
O11—C11 | 1.265 (3) | C32—C33 | 1.389 (4) |
O12—C11 | 1.241 (3) | C32—H32 | 0.95 |
O13—C14 | 1.220 (3) | C33—C34 | 1.377 (5) |
O14—C14 | 1.315 (4) | C33—H33 | 0.95 |
O14—H14 | 0.84 | C34—C35 | 1.380 (5) |
O15—C12 | 1.428 (3) | C34—H34 | 0.95 |
O15—H15 | 0.84 | C35—C36 | 1.389 (5) |
O16—C13 | 1.413 (3) | C35—H35 | 0.95 |
O16—H16 | 0.84 | C36—H36 | 0.95 |
C11—C12 | 1.536 (3) | C37—C38 | 1.523 (4) |
C12—C13 | 1.529 (4) | C37—H37 | 1.00 |
C12—H12A | 1.00 | C38—H38A | 0.98 |
C13—C14 | 1.529 (3) | C38—H38B | 0.98 |
C13—H13A | 1.00 | C38—H38C | 0.98 |
O21—C21 | 1.270 (3) | N4—C47 | 1.495 (4) |
O22—C21 | 1.239 (3) | N4—H4A | 0.91 |
O23—C24 | 1.212 (3) | N4—H4B | 0.91 |
O24—C24 | 1.319 (3) | N4—H4C | 0.91 |
O24—H24 | 0.84 | C41—C42 | 1.387 (4) |
O25—C22 | 1.416 (3) | C41—C46 | 1.393 (4) |
O25—H25 | 0.84 | C41—C47 | 1.514 (4) |
O26—C23 | 1.417 (3) | C42—C43 | 1.389 (4) |
O26—H26 | 0.84 | C42—H42 | 0.95 |
C21—C22 | 1.528 (4) | C43—C44 | 1.381 (5) |
C22—C23 | 1.519 (4) | C43—H43 | 0.95 |
C22—H22A | 1.00 | C44—C45 | 1.388 (5) |
C23—C24 | 1.532 (3) | C44—H44 | 0.95 |
C23—H23A | 1.00 | C45—C46 | 1.380 (4) |
N3—C37 | 1.499 (4) | C45—H45 | 0.95 |
N3—H3A | 0.91 | C46—H46 | 0.95 |
N3—H3B | 0.91 | C47—C48 | 1.521 (4) |
N3—H3C | 0.91 | C47—H47 | 1.00 |
C31—C36 | 1.387 (4) | C48—H48A | 0.98 |
C31—C32 | 1.392 (4) | C48—H48B | 0.98 |
C31—C37 | 1.506 (4) | C48—H48C | 0.98 |
C14—O14—H14 | 109.5 | C33—C34—C35 | 120.1 (3) |
C12—O15—H15 | 109.5 | C33—C34—H34 | 119.9 |
C13—O16—H16 | 109.5 | C35—C34—H34 | 119.9 |
O12—C11—O11 | 126.9 (2) | C34—C35—C36 | 119.9 (3) |
O12—C11—C12 | 116.6 (2) | C34—C35—H35 | 120.1 |
O11—C11—C12 | 116.5 (2) | C36—C35—H35 | 120.1 |
O15—C12—C13 | 108.8 (2) | C31—C36—C35 | 120.7 (3) |
O15—C12—C11 | 110.4 (2) | C31—C36—H36 | 119.6 |
C13—C12—C11 | 112.5 (2) | C35—C36—H36 | 119.6 |
O15—C12—H12A | 108.4 | N3—C37—C31 | 111.5 (2) |
C13—C12—H12A | 108.4 | N3—C37—C38 | 108.9 (2) |
C11—C12—H12A | 108.4 | C31—C37—C38 | 112.4 (2) |
O16—C13—C14 | 111.2 (2) | N3—C37—H37 | 108.0 |
O16—C13—C12 | 107.7 (2) | C31—C37—H37 | 108.0 |
C14—C13—C12 | 108.4 (2) | C38—C37—H37 | 108.0 |
O16—C13—H13A | 109.8 | C37—C38—H38A | 109.5 |
C14—C13—H13A | 109.8 | C37—C38—H38B | 109.5 |
C12—C13—H13A | 109.8 | H38A—C38—H38B | 109.5 |
O13—C14—O14 | 125.2 (2) | C37—C38—H38C | 109.5 |
O13—C14—C13 | 122.5 (3) | H38A—C38—H38C | 109.5 |
O14—C14—C13 | 112.3 (2) | H38B—C38—H38C | 109.5 |
C24—O24—H24 | 109.5 | C47—N4—H4A | 109.5 |
C22—O25—H25 | 109.5 | C47—N4—H4B | 109.5 |
C23—O26—H26 | 109.5 | H4A—N4—H4B | 109.5 |
O22—C21—O21 | 126.1 (2) | C47—N4—H4C | 109.5 |
O22—C21—C22 | 117.0 (2) | H4A—N4—H4C | 109.5 |
O21—C21—C22 | 116.9 (2) | H4B—N4—H4C | 109.5 |
O25—C22—C23 | 109.9 (2) | C42—C41—C46 | 118.7 (3) |
O25—C22—C21 | 110.8 (2) | C42—C41—C47 | 122.5 (3) |
C23—C22—C21 | 111.9 (2) | C46—C41—C47 | 118.6 (3) |
O25—C22—H22A | 108.0 | C41—C42—C43 | 120.4 (3) |
C23—C22—H22A | 108.0 | C41—C42—H42 | 119.8 |
C21—C22—H22A | 108.0 | C43—C42—H42 | 119.8 |
O26—C23—C22 | 108.1 (2) | C44—C43—C42 | 120.4 (3) |
O26—C23—C24 | 110.9 (2) | C44—C43—H43 | 119.8 |
C22—C23—C24 | 108.8 (2) | C42—C43—H43 | 119.8 |
O26—C23—H23A | 109.7 | C43—C44—C45 | 119.5 (3) |
C22—C23—H23A | 109.7 | C43—C44—H44 | 120.3 |
C24—C23—H23A | 109.7 | C45—C44—H44 | 120.3 |
O23—C24—O24 | 125.4 (2) | C46—C45—C44 | 120.1 (3) |
O23—C24—C23 | 123.3 (3) | C46—C45—H45 | 119.9 |
O24—C24—C23 | 111.2 (2) | C44—C45—H45 | 119.9 |
C37—N3—H3A | 109.5 | C45—C46—C41 | 120.9 (3) |
C37—N3—H3B | 109.5 | C45—C46—H46 | 119.6 |
H3A—N3—H3B | 109.5 | C41—C46—H46 | 119.6 |
C37—N3—H3C | 109.5 | N4—C47—C41 | 111.9 (2) |
H3A—N3—H3C | 109.5 | N4—C47—C48 | 108.8 (2) |
H3B—N3—H3C | 109.5 | C41—C47—C48 | 111.7 (2) |
C36—C31—C32 | 118.6 (3) | N4—C47—H47 | 108.1 |
C36—C31—C37 | 120.3 (3) | C41—C47—H47 | 108.1 |
C32—C31—C37 | 120.9 (3) | C48—C47—H47 | 108.1 |
C33—C32—C31 | 120.6 (3) | C47—C48—H48A | 109.5 |
C33—C32—H32 | 119.7 | C47—C48—H48B | 109.5 |
C31—C32—H32 | 119.7 | H48A—C48—H48B | 109.5 |
C34—C33—C32 | 120.0 (3) | C47—C48—H48C | 109.5 |
C34—C33—H33 | 120.0 | H48A—C48—H48C | 109.5 |
C32—C33—H33 | 120.0 | H48B—C48—H48C | 109.5 |
O12—C11—C12—O15 | −8.0 (3) | C36—C31—C32—C33 | 0.2 (5) |
O11—C11—C12—O15 | 174.8 (2) | C37—C31—C32—C33 | 175.7 (3) |
O12—C11—C12—C13 | −129.7 (3) | C31—C32—C33—C34 | −0.9 (5) |
O11—C11—C12—C13 | 53.1 (3) | C32—C33—C34—C35 | 0.7 (5) |
O15—C12—C13—O16 | −66.8 (2) | C33—C34—C35—C36 | 0.1 (5) |
C11—C12—C13—O16 | 55.8 (3) | C32—C31—C36—C35 | 0.6 (5) |
O15—C12—C13—C14 | 53.6 (3) | C37—C31—C36—C35 | −174.9 (3) |
C11—C12—C13—C14 | 176.2 (2) | C34—C35—C36—C31 | −0.8 (5) |
O16—C13—C14—O13 | 2.9 (4) | C36—C31—C37—N3 | −128.2 (3) |
C12—C13—C14—O13 | −115.3 (3) | C32—C31—C37—N3 | 56.4 (4) |
O16—C13—C14—O14 | −179.0 (2) | C36—C31—C37—C38 | 109.2 (3) |
C12—C13—C14—O14 | 62.8 (3) | C32—C31—C37—C38 | −66.2 (4) |
O22—C21—C22—O25 | 4.4 (3) | C46—C41—C42—C43 | 0.6 (4) |
O21—C21—C22—O25 | −177.8 (2) | C47—C41—C42—C43 | 175.5 (3) |
O22—C21—C22—C23 | 127.4 (3) | C41—C42—C43—C44 | −0.7 (4) |
O21—C21—C22—C23 | −54.8 (3) | C42—C43—C44—C45 | 0.2 (4) |
O25—C22—C23—O26 | 69.1 (3) | C43—C44—C45—C46 | 0.4 (4) |
C21—C22—C23—O26 | −54.5 (3) | C44—C45—C46—C41 | −0.5 (4) |
O25—C22—C23—C24 | −51.4 (3) | C42—C41—C46—C45 | 0.0 (4) |
C21—C22—C23—C24 | −175.0 (2) | C47—C41—C46—C45 | −175.1 (3) |
O26—C23—C24—O23 | −1.7 (4) | C42—C41—C47—N4 | 38.1 (4) |
C22—C23—C24—O23 | 117.1 (3) | C46—C41—C47—N4 | −147.0 (3) |
O26—C23—C24—O24 | 180.0 (2) | C42—C41—C47—C48 | −84.1 (3) |
C22—C23—C24—O24 | −61.2 (3) | C46—C41—C47—C48 | 90.8 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O15—H15···O12 | 0.84 | 2.13 | 2.605 (2) | 116 |
O15—H15···O22i | 0.84 | 2.22 | 2.944 (3) | 144 |
O16—H16···O21 | 0.84 | 1.92 | 2.750 (3) | 170 |
O14—H14···O11ii | 0.84 | 1.73 | 2.568 (2) | 176 |
O25—H25···O22 | 0.84 | 2.11 | 2.604 (2) | 117 |
O25—H25···O12iii | 0.84 | 2.35 | 3.019 (3) | 136 |
O26—H26···O11 | 0.84 | 1.94 | 2.773 (3) | 169 |
O24—H24···O21iv | 0.84 | 1.74 | 2.575 (2) | 177 |
N3—H3A···O26i | 0.91 | 2.11 | 2.945 (3) | 152 |
N3—H3A···O23i | 0.91 | 2.35 | 2.893 (3) | 118 |
N3—H3B···O15iv | 0.91 | 1.96 | 2.847 (3) | 165 |
N3—H3C···O12 | 0.91 | 1.85 | 2.747 (3) | 167 |
N4—H4A···O16iii | 0.91 | 2.15 | 2.956 (3) | 147 |
N4—H4A···O13iii | 0.91 | 2.25 | 2.916 (3) | 129 |
N4—H4B···O25ii | 0.91 | 1.93 | 2.824 (3) | 169 |
N4—H4C···O22 | 0.91 | 1.87 | 2.752 (3) | 162 |
C36—H36···Cgv | 0.95 | 2.87 | 3.775 (3) | 160 |
Symmetry codes: (i) x, y, z+1; (ii) x+1, y, z; (iii) x, y, z−1; (iv) x−1, y, z; (v) −x+1, y−1/2, −z+1. |
2(C8H12N)·C4H4O6 | F(000) = 420 |
Mr = 392.44 | Dx = 1.267 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 2434 reflections |
a = 5.5620 (2) Å | θ = 3.1–27.5° |
b = 16.0630 (3) Å | µ = 0.09 mm−1 |
c = 11.8260 (4) Å | T = 150 K |
β = 103.2810 (12)° | Plate, colourless |
V = 1028.31 (5) Å3 | 0.36 × 0.26 × 0.10 mm |
Z = 2 |
Kappa-CCD diffractometer | 2434 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 2187 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.050 |
ϕ scans, and ω scans with κ offsets | θmax = 27.5°, θmin = 3.1° |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | h = −7→7 |
Tmin = 0.877, Tmax = 0.995 | k = −20→19 |
8194 measured reflections | l = −14→15 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.035 | H-atom parameters constrained |
wR(F2) = 0.094 | w = 1/[σ2(Fo2) + (0.0574P)2 + 0.0872P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
2434 reflections | Δρmax = 0.22 e Å−3 |
260 parameters | Δρmin = −0.24 e Å−3 |
1 restraint | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.036 (7) |
2(C8H12N)·C4H4O6 | V = 1028.31 (5) Å3 |
Mr = 392.44 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 5.5620 (2) Å | µ = 0.09 mm−1 |
b = 16.0630 (3) Å | T = 150 K |
c = 11.8260 (4) Å | 0.36 × 0.26 × 0.10 mm |
β = 103.2810 (12)° |
Kappa-CCD diffractometer | 2434 independent reflections |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | 2187 reflections with I > 2σ(I) |
Tmin = 0.877, Tmax = 0.995 | Rint = 0.050 |
8194 measured reflections |
R[F2 > 2σ(F2)] = 0.035 | 1 restraint |
wR(F2) = 0.094 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.22 e Å−3 |
2434 reflections | Δρmin = −0.24 e Å−3 |
260 parameters |
x | y | z | Uiso*/Ueq | ||
O1 | −0.1580 (3) | 0.78816 (10) | 0.44636 (15) | 0.0356 (4) | |
O2 | 0.1833 (3) | 0.85005 (10) | 0.54792 (15) | 0.0368 (4) | |
O3 | 0.4876 (3) | 0.60682 (11) | 0.29174 (16) | 0.0419 (4) | |
O4 | 0.2168 (3) | 0.54276 (9) | 0.37515 (14) | 0.0324 (4) | |
O5 | 0.4621 (3) | 0.71189 (10) | 0.54093 (13) | 0.0294 (3) | |
O6 | 0.3040 (3) | 0.75508 (10) | 0.30065 (13) | 0.0314 (4) | |
C1 | 0.0678 (4) | 0.78956 (13) | 0.49291 (18) | 0.0261 (4) | |
C2 | 0.2123 (4) | 0.70972 (12) | 0.48037 (17) | 0.0224 (4) | |
C3 | 0.1882 (4) | 0.69053 (13) | 0.35161 (18) | 0.0246 (4) | |
C4 | 0.3079 (4) | 0.60629 (13) | 0.33763 (17) | 0.0263 (4) | |
N1 | 0.4500 (3) | 0.42380 (10) | 0.53992 (14) | 0.0237 (4) | |
C11 | 0.4643 (4) | 0.49557 (13) | 0.72661 (17) | 0.0244 (4) | |
C12 | 0.4416 (4) | 0.58029 (14) | 0.74569 (18) | 0.0276 (4) | |
C13 | 0.3044 (4) | 0.60863 (15) | 0.8228 (2) | 0.0326 (5) | |
C14 | 0.1926 (4) | 0.55224 (16) | 0.8827 (2) | 0.0369 (5) | |
C15 | 0.2132 (4) | 0.46768 (17) | 0.8641 (2) | 0.0368 (5) | |
C16 | 0.3480 (4) | 0.43945 (14) | 0.78661 (19) | 0.0304 (5) | |
C17 | 0.6180 (3) | 0.46243 (13) | 0.64525 (17) | 0.0245 (4) | |
C18 | 0.7785 (4) | 0.52599 (14) | 0.60186 (19) | 0.0273 (4) | |
N2 | −0.2307 (3) | 0.47010 (11) | 0.27975 (14) | 0.0252 (4) | |
C21 | −0.1154 (4) | 0.37692 (12) | 0.13222 (18) | 0.0245 (4) | |
C22 | 0.1016 (4) | 0.35321 (15) | 0.2096 (2) | 0.0321 (5) | |
C23 | 0.2448 (4) | 0.28855 (16) | 0.1819 (2) | 0.0368 (5) | |
C24 | 0.1730 (4) | 0.24790 (15) | 0.0766 (2) | 0.0348 (5) | |
C25 | −0.0427 (5) | 0.27039 (15) | −0.0009 (2) | 0.0384 (6) | |
C26 | −0.1873 (4) | 0.33410 (14) | 0.02711 (19) | 0.0329 (5) | |
C27 | −0.2724 (4) | 0.44953 (13) | 0.15384 (17) | 0.0252 (4) | |
C28 | −0.2211 (5) | 0.52813 (14) | 0.09017 (19) | 0.0329 (5) | |
H5 | 0.5448 | 0.7384 | 0.5018 | 0.044* | |
H6 | 0.4363 | 0.7371 | 0.2869 | 0.047* | |
H2 | 0.1319 | 0.6630 | 0.5137 | 0.027* | |
H3 | 0.0090 | 0.6882 | 0.3118 | 0.030* | |
H1A | 0.5424 | 0.3961 | 0.4977 | 0.036* | |
H1B | 0.3612 | 0.4645 | 0.4954 | 0.036* | |
H1C | 0.3452 | 0.3875 | 0.5631 | 0.036* | |
H12 | 0.5204 | 0.6193 | 0.7057 | 0.033* | |
H13 | 0.2877 | 0.6667 | 0.8343 | 0.039* | |
H14 | 0.1018 | 0.5715 | 0.9365 | 0.044* | |
H15 | 0.1348 | 0.4289 | 0.9046 | 0.044* | |
H16 | 0.3613 | 0.3814 | 0.7743 | 0.036* | |
H17 | 0.7285 | 0.4177 | 0.6872 | 0.029* | |
H18A | 0.6733 | 0.5690 | 0.5567 | 0.041* | |
H18B | 0.8736 | 0.4982 | 0.5526 | 0.041* | |
H18C | 0.8921 | 0.5518 | 0.6683 | 0.041* | |
H2A | −0.0786 | 0.4934 | 0.3046 | 0.038* | |
H2B | −0.2401 | 0.4228 | 0.3208 | 0.038* | |
H2C | −0.3482 | 0.5067 | 0.2907 | 0.038* | |
H22 | 0.1526 | 0.3813 | 0.2819 | 0.039* | |
H23 | 0.3921 | 0.2724 | 0.2355 | 0.044* | |
H24 | 0.2723 | 0.2044 | 0.0575 | 0.042* | |
H25 | −0.0921 | 0.2423 | −0.0732 | 0.046* | |
H26 | −0.3370 | 0.3488 | −0.0259 | 0.039* | |
H27 | −0.4501 | 0.4342 | 0.1246 | 0.030* | |
H28A | −0.0467 | 0.5436 | 0.1168 | 0.049* | |
H28B | −0.3251 | 0.5737 | 0.1066 | 0.049* | |
H28C | −0.2584 | 0.5175 | 0.0063 | 0.049* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0277 (8) | 0.0282 (8) | 0.0539 (10) | 0.0071 (6) | 0.0155 (7) | 0.0018 (7) |
O2 | 0.0546 (10) | 0.0226 (8) | 0.0398 (9) | −0.0097 (7) | 0.0243 (8) | −0.0103 (6) |
O3 | 0.0505 (10) | 0.0331 (9) | 0.0487 (10) | 0.0117 (8) | 0.0246 (9) | −0.0019 (7) |
O4 | 0.0382 (8) | 0.0197 (7) | 0.0343 (8) | 0.0006 (6) | −0.0020 (7) | −0.0007 (6) |
O5 | 0.0259 (8) | 0.0352 (9) | 0.0255 (7) | −0.0007 (6) | 0.0028 (6) | 0.0018 (6) |
O6 | 0.0434 (9) | 0.0241 (8) | 0.0291 (8) | 0.0046 (6) | 0.0130 (7) | 0.0048 (6) |
C1 | 0.0341 (11) | 0.0198 (9) | 0.0301 (10) | 0.0007 (8) | 0.0193 (9) | −0.0002 (8) |
C2 | 0.0238 (10) | 0.0201 (9) | 0.0238 (9) | 0.0000 (7) | 0.0066 (7) | −0.0008 (7) |
C3 | 0.0273 (10) | 0.0210 (10) | 0.0244 (9) | 0.0030 (7) | 0.0037 (8) | −0.0015 (7) |
C4 | 0.0299 (10) | 0.0231 (10) | 0.0230 (10) | 0.0051 (8) | 0.0002 (8) | −0.0027 (8) |
N1 | 0.0261 (8) | 0.0206 (8) | 0.0246 (8) | −0.0021 (6) | 0.0060 (7) | −0.0006 (7) |
C11 | 0.0233 (10) | 0.0269 (10) | 0.0217 (9) | −0.0011 (7) | 0.0022 (8) | 0.0029 (7) |
C12 | 0.0290 (10) | 0.0267 (11) | 0.0265 (10) | −0.0020 (8) | 0.0054 (8) | −0.0010 (8) |
C13 | 0.0333 (11) | 0.0316 (11) | 0.0330 (11) | −0.0031 (9) | 0.0080 (9) | −0.0068 (9) |
C14 | 0.0365 (12) | 0.0489 (15) | 0.0275 (11) | −0.0020 (10) | 0.0119 (9) | −0.0031 (10) |
C15 | 0.0371 (12) | 0.0452 (14) | 0.0296 (11) | −0.0065 (10) | 0.0109 (9) | 0.0098 (10) |
C16 | 0.0325 (11) | 0.0273 (11) | 0.0294 (10) | −0.0022 (8) | 0.0033 (9) | 0.0069 (8) |
C17 | 0.0227 (9) | 0.0227 (10) | 0.0268 (10) | −0.0006 (7) | 0.0033 (8) | 0.0009 (8) |
C18 | 0.0236 (9) | 0.0271 (11) | 0.0312 (10) | −0.0030 (8) | 0.0061 (8) | −0.0008 (8) |
N2 | 0.0303 (9) | 0.0231 (9) | 0.0238 (8) | 0.0029 (7) | 0.0097 (7) | 0.0020 (7) |
C21 | 0.0278 (10) | 0.0239 (10) | 0.0222 (9) | 0.0004 (8) | 0.0065 (8) | 0.0017 (7) |
C22 | 0.0333 (12) | 0.0320 (11) | 0.0284 (11) | 0.0042 (9) | 0.0017 (9) | −0.0065 (9) |
C23 | 0.0351 (12) | 0.0332 (12) | 0.0394 (12) | 0.0083 (10) | 0.0030 (10) | −0.0036 (10) |
C24 | 0.0418 (13) | 0.0269 (11) | 0.0369 (12) | 0.0066 (9) | 0.0113 (10) | −0.0047 (9) |
C25 | 0.0522 (14) | 0.0350 (14) | 0.0272 (11) | 0.0040 (10) | 0.0076 (10) | −0.0068 (9) |
C26 | 0.0383 (12) | 0.0330 (12) | 0.0244 (10) | 0.0048 (9) | 0.0013 (9) | −0.0005 (9) |
C27 | 0.0281 (10) | 0.0241 (10) | 0.0236 (10) | 0.0015 (7) | 0.0064 (8) | 0.0009 (8) |
C28 | 0.0441 (12) | 0.0278 (11) | 0.0281 (11) | 0.0058 (9) | 0.0112 (9) | 0.0074 (8) |
O1—C1 | 1.250 (3) | C16—H16 | 0.95 |
O2—C1 | 1.260 (3) | C17—C18 | 1.521 (3) |
O3—C4 | 1.242 (3) | C17—H17 | 1.00 |
O4—C4 | 1.264 (3) | C18—H18A | 0.98 |
O5—C2 | 1.409 (2) | C18—H18B | 0.98 |
O5—H5 | 0.84 | C18—H18C | 0.98 |
O6—C3 | 1.426 (3) | N2—C27 | 1.491 (3) |
O6—H6 | 0.84 | N2—H2A | 0.91 |
C1—C2 | 1.539 (3) | N2—H2B | 0.91 |
C2—C3 | 1.529 (3) | N2—H2C | 0.91 |
C2—H2 | 1.00 | C21—C22 | 1.390 (3) |
C3—C4 | 1.534 (3) | C21—C26 | 1.396 (3) |
C3—H3 | 1.00 | C21—C27 | 1.514 (3) |
N1—C17 | 1.508 (2) | C22—C23 | 1.393 (3) |
N1—H1A | 0.91 | C22—H22 | 0.95 |
N1—H1B | 0.91 | C23—C24 | 1.381 (3) |
N1—H1C | 0.91 | C23—H23 | 0.95 |
C11—C12 | 1.390 (3) | C24—C25 | 1.380 (4) |
C11—C16 | 1.395 (3) | C24—H24 | 0.95 |
C11—C17 | 1.522 (3) | C25—C26 | 1.388 (3) |
C12—C13 | 1.394 (3) | C25—H25 | 0.95 |
C12—H12 | 0.95 | C26—H26 | 0.95 |
C13—C14 | 1.382 (3) | C27—C28 | 1.530 (3) |
C13—H13 | 0.95 | C27—H27 | 1.00 |
C14—C15 | 1.385 (4) | C28—H28A | 0.98 |
C14—H14 | 0.95 | C28—H28B | 0.98 |
C15—C16 | 1.387 (3) | C28—H28C | 0.98 |
C15—H15 | 0.95 | ||
C2—O5—H5 | 109.5 | C18—C17—C11 | 115.91 (17) |
C3—O6—H6 | 109.5 | N1—C17—H17 | 107.9 |
O1—C1—O2 | 125.6 (2) | C18—C17—H17 | 107.9 |
O1—C1—C2 | 115.90 (18) | C11—C17—H17 | 107.9 |
O2—C1—C2 | 118.46 (19) | C17—C18—H18A | 109.5 |
O5—C2—C3 | 111.23 (16) | C17—C18—H18B | 109.5 |
O5—C2—C1 | 113.96 (17) | H18A—C18—H18B | 109.5 |
C3—C2—C1 | 109.61 (16) | C17—C18—H18C | 109.5 |
O5—C2—H2 | 107.2 | H18A—C18—H18C | 109.5 |
C3—C2—H2 | 107.2 | H18B—C18—H18C | 109.5 |
C1—C2—H2 | 107.2 | C27—N2—H2A | 109.5 |
O6—C3—C2 | 109.24 (16) | C27—N2—H2B | 109.5 |
O6—C3—C4 | 110.27 (17) | H2A—N2—H2B | 109.5 |
C2—C3—C4 | 110.13 (16) | C27—N2—H2C | 109.5 |
O6—C3—H3 | 109.1 | H2A—N2—H2C | 109.5 |
C2—C3—H3 | 109.1 | H2B—N2—H2C | 109.5 |
C4—C3—H3 | 109.1 | C22—C21—C26 | 118.62 (19) |
O3—C4—O4 | 125.9 (2) | C22—C21—C27 | 123.18 (18) |
O3—C4—C3 | 117.0 (2) | C26—C21—C27 | 118.14 (18) |
O4—C4—C3 | 117.09 (18) | C21—C22—C23 | 120.4 (2) |
C17—N1—H1A | 109.5 | C21—C22—H22 | 119.8 |
C17—N1—H1B | 109.5 | C23—C22—H22 | 119.8 |
H1A—N1—H1B | 109.5 | C24—C23—C22 | 120.2 (2) |
C17—N1—H1C | 109.5 | C24—C23—H23 | 119.9 |
H1A—N1—H1C | 109.5 | C22—C23—H23 | 119.9 |
H1B—N1—H1C | 109.5 | C25—C24—C23 | 120.1 (2) |
C12—C11—C16 | 118.7 (2) | C25—C24—H24 | 119.9 |
C12—C11—C17 | 122.01 (18) | C23—C24—H24 | 119.9 |
C16—C11—C17 | 119.27 (19) | C24—C25—C26 | 119.8 (2) |
C11—C12—C13 | 120.7 (2) | C24—C25—H25 | 120.1 |
C11—C12—H12 | 119.7 | C26—C25—H25 | 120.1 |
C13—C12—H12 | 119.7 | C25—C26—C21 | 120.8 (2) |
C14—C13—C12 | 120.0 (2) | C25—C26—H26 | 119.6 |
C14—C13—H13 | 120.0 | C21—C26—H26 | 119.6 |
C12—C13—H13 | 120.0 | N2—C27—C21 | 112.10 (16) |
C13—C14—C15 | 119.9 (2) | N2—C27—C28 | 107.75 (17) |
C13—C14—H14 | 120.1 | C21—C27—C28 | 111.86 (17) |
C15—C14—H14 | 120.1 | N2—C27—H27 | 108.3 |
C14—C15—C16 | 120.2 (2) | C21—C27—H27 | 108.3 |
C14—C15—H15 | 119.9 | C28—C27—H27 | 108.3 |
C16—C15—H15 | 119.9 | C27—C28—H28A | 109.5 |
C15—C16—C11 | 120.6 (2) | C27—C28—H28B | 109.5 |
C15—C16—H16 | 119.7 | H28A—C28—H28B | 109.5 |
C11—C16—H16 | 119.7 | C27—C28—H28C | 109.5 |
N1—C17—C18 | 107.32 (16) | H28A—C28—H28C | 109.5 |
N1—C17—C11 | 109.56 (15) | H28B—C28—H28C | 109.5 |
O1—C1—C2—O5 | −175.79 (18) | C12—C11—C16—C15 | −0.3 (3) |
O2—C1—C2—O5 | 4.3 (3) | C17—C11—C16—C15 | 177.96 (19) |
O1—C1—C2—C3 | 58.8 (2) | C12—C11—C17—N1 | −111.8 (2) |
O2—C1—C2—C3 | −121.1 (2) | C16—C11—C17—N1 | 70.0 (2) |
O5—C2—C3—O6 | −62.2 (2) | C12—C11—C17—C18 | 9.7 (3) |
C1—C2—C3—O6 | 64.8 (2) | C16—C11—C17—C18 | −168.40 (18) |
O5—C2—C3—C4 | 59.1 (2) | C26—C21—C22—C23 | 0.6 (3) |
C1—C2—C3—C4 | −173.98 (16) | C27—C21—C22—C23 | −176.6 (2) |
O6—C3—C4—O3 | 3.5 (3) | C21—C22—C23—C24 | 0.5 (4) |
C2—C3—C4—O3 | −117.2 (2) | C22—C23—C24—C25 | −0.9 (4) |
O6—C3—C4—O4 | −177.40 (17) | C23—C24—C25—C26 | 0.1 (4) |
C2—C3—C4—O4 | 62.0 (2) | C24—C25—C26—C21 | 1.0 (4) |
C16—C11—C12—C13 | −0.3 (3) | C22—C21—C26—C25 | −1.4 (3) |
C17—C11—C12—C13 | −178.45 (19) | C27—C21—C26—C25 | 175.9 (2) |
C11—C12—C13—C14 | 1.1 (3) | C22—C21—C27—N2 | −22.7 (3) |
C12—C13—C14—C15 | −1.3 (4) | C26—C21—C27—N2 | 160.08 (19) |
C13—C14—C15—C16 | 0.7 (4) | C22—C21—C27—C28 | 98.5 (2) |
C14—C15—C16—C11 | 0.0 (3) | C26—C21—C27—C28 | −78.8 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5···O1i | 0.84 | 2.07 | 2.882 (2) | 161 |
O5—H5···O6 | 0.84 | 2.46 | 2.860 (2) | 110 |
O6—H6···O3 | 0.84 | 2.11 | 2.603 (2) | 117 |
N1—H1A···O2ii | 0.91 | 1.88 | 2.759 (2) | 161 |
N1—H1B···O4 | 0.91 | 1.93 | 2.823 (2) | 167 |
N1—H1C···O1iii | 0.91 | 1.89 | 2.745 (2) | 155 |
N2—H2A···O4 | 0.91 | 1.84 | 2.746 (2) | 172 |
N2—H2B···O2iii | 0.91 | 1.91 | 2.774 (2) | 158 |
N2—H2C···O3iv | 0.91 | 1.85 | 2.720 (2) | 159 |
Symmetry codes: (i) x+1, y, z; (ii) −x+1, y−1/2, −z+1; (iii) −x, y−1/2, −z+1; (iv) x−1, y, z. |
2(C8H12N)·C4H4O6 | F(000) = 840 |
Mr = 392.44 | Dx = 1.271 Mg m−3 |
Monoclinic, P21 | Synchrotron radiation, λ = 0.6900 Å |
Hall symbol: P 2yb | Cell parameters from 5818 reflections |
a = 8.3381 (14) Å | θ = 1.7–29.4° |
b = 22.738 (4) Å | µ = 0.09 mm−1 |
c = 10.8190 (18) Å | T = 150 K |
β = 90.120 (3)° | Plate, colourless |
V = 2051.2 (6) Å3 | 0.30 × 0.22 × 0.06 mm |
Z = 4 |
Kappa-CCD diffractometer | 5504 reflections with I > 2σ(I) |
Radiation source: synchrotron | Rint = 0.034 |
ϕ scans, and ω scans with κ offsets | θmax = 29.4°, θmin = 1.7° |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | h = −11→11 |
Tmin = 0.972, Tmax = 0.994 | k = −30→30 |
18641 measured reflections | l = −15→14 |
5818 independent reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.151 | H-atom parameters constrained |
S = 1.16 | w = 1/[σ2(Fo2) + (0.0842P)2 + 0.5384P] where P = (Fo2 + 2Fc2)/3 |
5818 reflections | (Δ/σ)max = 0.001 |
517 parameters | Δρmax = 0.59 e Å−3 |
1 restraint | Δρmin = −0.34 e Å−3 |
2(C8H12N)·C4H4O6 | V = 2051.2 (6) Å3 |
Mr = 392.44 | Z = 4 |
Monoclinic, P21 | Synchrotron radiation, λ = 0.6900 Å |
a = 8.3381 (14) Å | µ = 0.09 mm−1 |
b = 22.738 (4) Å | T = 150 K |
c = 10.8190 (18) Å | 0.30 × 0.22 × 0.06 mm |
β = 90.120 (3)° |
Kappa-CCD diffractometer | 5818 independent reflections |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | 5504 reflections with I > 2σ(I) |
Tmin = 0.972, Tmax = 0.994 | Rint = 0.034 |
18641 measured reflections |
R[F2 > 2σ(F2)] = 0.054 | 1 restraint |
wR(F2) = 0.151 | H-atom parameters constrained |
S = 1.16 | Δρmax = 0.59 e Å−3 |
5818 reflections | Δρmin = −0.34 e Å−3 |
517 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
O11 | 0.3959 (2) | 0.48525 (10) | 0.76691 (19) | 0.0302 (4) | |
O12 | 0.3469 (2) | 0.56775 (9) | 0.87050 (17) | 0.0259 (4) | |
O13 | 0.8339 (2) | 0.52948 (11) | 1.16414 (19) | 0.0325 (4) | |
O14 | 0.8851 (2) | 0.58334 (11) | 0.99741 (18) | 0.0299 (4) | |
O15 | 0.6974 (2) | 0.47686 (9) | 0.85069 (17) | 0.0257 (4) | |
H15 | 0.7620 | 0.4826 | 0.7925 | 0.039* | |
O16 | 0.5463 (2) | 0.49404 (10) | 1.07704 (17) | 0.0283 (4) | |
H16 | 0.5058 | 0.5059 | 1.1436 | 0.042* | |
C11 | 0.4381 (3) | 0.52675 (12) | 0.8356 (2) | 0.0202 (4) | |
C12 | 0.6148 (3) | 0.52957 (12) | 0.8771 (2) | 0.0194 (4) | |
H12 | 0.6687 | 0.5626 | 0.8325 | 0.023* | |
C13 | 0.6220 (3) | 0.54174 (12) | 1.0160 (2) | 0.0205 (4) | |
H13 | 0.5588 | 0.5782 | 1.0331 | 0.025* | |
C14 | 0.7944 (3) | 0.55160 (12) | 1.0615 (2) | 0.0222 (5) | |
O21 | −0.1309 (2) | 0.42473 (10) | 0.49823 (19) | 0.0281 (4) | |
O22 | −0.0807 (2) | 0.47946 (11) | 0.66396 (19) | 0.0314 (4) | |
O23 | 0.3618 (2) | 0.52484 (11) | 0.27015 (19) | 0.0311 (4) | |
O24 | 0.4064 (2) | 0.44174 (10) | 0.37315 (18) | 0.0266 (4) | |
O25 | 0.2057 (2) | 0.51542 (10) | 0.57711 (17) | 0.0280 (4) | |
H25 | 0.2531 | 0.5029 | 0.6404 | 0.042* | |
O26 | 0.0582 (2) | 0.53313 (10) | 0.34984 (17) | 0.0267 (4) | |
H26 | −0.0054 | 0.5275 | 0.2907 | 0.040* | |
C21 | −0.0411 (3) | 0.45736 (12) | 0.5619 (2) | 0.0217 (5) | |
C22 | 0.1308 (3) | 0.46791 (12) | 0.5153 (2) | 0.0210 (5) | |
H22 | 0.1949 | 0.4316 | 0.5322 | 0.025* | |
C23 | 0.1396 (3) | 0.48055 (12) | 0.3772 (2) | 0.0205 (4) | |
H23 | 0.0860 | 0.4476 | 0.3318 | 0.025* | |
C24 | 0.3177 (3) | 0.48294 (13) | 0.3376 (2) | 0.0219 (5) | |
C31 | −0.1566 (4) | 0.63264 (14) | 0.6447 (3) | 0.0328 (6) | |
C32 | −0.2708 (4) | 0.66246 (17) | 0.7127 (3) | 0.0388 (7) | |
H32 | −0.2404 | 0.6839 | 0.7844 | 0.047* | |
C33 | −0.4310 (4) | 0.6609 (2) | 0.6753 (4) | 0.0512 (10) | |
H33 | −0.5092 | 0.6824 | 0.7205 | 0.061* | |
C34 | −0.4772 (5) | 0.6286 (2) | 0.5735 (5) | 0.0615 (13) | |
H34 | −0.5870 | 0.6266 | 0.5503 | 0.074* | |
C35 | −0.3631 (6) | 0.5993 (2) | 0.5060 (5) | 0.0639 (13) | |
H35 | −0.3940 | 0.5770 | 0.4355 | 0.077* | |
C36 | −0.2022 (5) | 0.60200 (18) | 0.5404 (4) | 0.0465 (9) | |
H36 | −0.1234 | 0.5827 | 0.4918 | 0.056* | |
C37 | 0.0170 (4) | 0.62933 (18) | 0.6851 (4) | 0.0452 (9) | |
H37 | 0.0807 | 0.6202 | 0.6092 | 0.054* | |
C38 | 0.0875 (6) | 0.6821 (2) | 0.7386 (7) | 0.0802 (19) | |
H38A | 0.0250 | 0.6942 | 0.8109 | 0.120* | |
H38B | 0.0867 | 0.7138 | 0.6771 | 0.120* | |
H38C | 0.1982 | 0.6740 | 0.7637 | 0.120* | |
N3 | 0.0384 (3) | 0.57865 (12) | 0.7700 (2) | 0.0261 (5) | |
H3A | 0.1425 | 0.5769 | 0.7953 | 0.039* | |
H3B | 0.0124 | 0.5448 | 0.7299 | 0.039* | |
H3C | −0.0264 | 0.5832 | 0.8369 | 0.039* | |
C41 | 1.3613 (4) | 0.67717 (14) | 1.1196 (3) | 0.0335 (6) | |
C42 | 1.4098 (6) | 0.7115 (2) | 1.0210 (4) | 0.0526 (10) | |
H42 | 1.3367 | 0.7199 | 0.9559 | 0.063* | |
C43 | 1.5659 (7) | 0.7337 (3) | 1.0167 (5) | 0.0719 (16) | |
H43 | 1.5980 | 0.7574 | 0.9488 | 0.086* | |
C44 | 1.6709 (5) | 0.7220 (2) | 1.1075 (5) | 0.0642 (14) | |
H44 | 1.7768 | 0.7373 | 1.1033 | 0.077* | |
C45 | 1.6251 (5) | 0.6874 (2) | 1.2082 (5) | 0.0554 (11) | |
H45 | 1.6992 | 0.6791 | 1.2727 | 0.066* | |
C46 | 1.4697 (4) | 0.66522 (17) | 1.2127 (4) | 0.0405 (7) | |
H46 | 1.4379 | 0.6416 | 1.2807 | 0.049* | |
C47 | 1.1919 (3) | 0.65292 (15) | 1.1208 (3) | 0.0346 (6) | |
H47 | 1.1327 | 0.6714 | 1.0504 | 0.041* | |
C48 | 1.0991 (5) | 0.6659 (2) | 1.2365 (5) | 0.0550 (10) | |
H48A | 0.9940 | 0.6466 | 1.2319 | 0.082* | |
H48B | 1.0844 | 0.7084 | 1.2446 | 0.082* | |
H48C | 1.1582 | 0.6509 | 1.3083 | 0.082* | |
N4 | 1.1937 (2) | 0.58875 (11) | 1.0989 (2) | 0.0247 (4) | |
H4A | 1.2372 | 0.5703 | 1.1656 | 0.037* | |
H4B | 1.2534 | 0.5807 | 1.0307 | 0.037* | |
H4C | 1.0916 | 0.5758 | 1.0870 | 0.037* | |
C51 | 0.9062 (3) | 0.37519 (14) | 1.1482 (3) | 0.0291 (5) | |
C52 | 0.9509 (4) | 0.40679 (17) | 1.0440 (3) | 0.0407 (7) | |
H52 | 0.8715 | 0.4260 | 0.9956 | 0.049* | |
C53 | 1.1117 (5) | 0.4104 (2) | 1.0102 (4) | 0.0554 (11) | |
H53 | 1.1414 | 0.4329 | 0.9399 | 0.066* | |
C54 | 1.2278 (5) | 0.3818 (2) | 1.0775 (4) | 0.0549 (11) | |
H54 | 1.3372 | 0.3845 | 1.0538 | 0.066* | |
C55 | 1.1846 (4) | 0.3492 (2) | 1.1798 (4) | 0.0462 (9) | |
H55 | 1.2642 | 0.3287 | 1.2257 | 0.055* | |
C56 | 1.0240 (4) | 0.34625 (15) | 1.2160 (3) | 0.0342 (6) | |
H56 | 0.9952 | 0.3243 | 1.2873 | 0.041* | |
C57 | 0.7335 (3) | 0.37795 (15) | 1.1905 (3) | 0.0320 (6) | |
H57 | 0.6638 | 0.3831 | 1.1159 | 0.038* | |
C58 | 0.6725 (5) | 0.32510 (19) | 1.2629 (5) | 0.0519 (9) | |
H58A | 0.7399 | 0.3191 | 1.3361 | 0.078* | |
H58B | 0.6767 | 0.2900 | 1.2105 | 0.078* | |
H58C | 0.5615 | 0.3322 | 1.2886 | 0.078* | |
N5 | 0.7135 (3) | 0.43108 (11) | 1.2718 (2) | 0.0253 (4) | |
H5A | 0.7819 | 0.4285 | 1.3372 | 0.038* | |
H5B | 0.6107 | 0.4327 | 1.2998 | 0.038* | |
H5C | 0.7357 | 0.4641 | 1.2276 | 0.038* | |
C61 | 0.3822 (3) | 0.33194 (13) | 0.6272 (3) | 0.0258 (5) | |
C62 | 0.3332 (4) | 0.29366 (16) | 0.5349 (3) | 0.0383 (7) | |
H62 | 0.4088 | 0.2791 | 0.4769 | 0.046* | |
C63 | 0.1723 (5) | 0.27648 (18) | 0.5271 (4) | 0.0483 (9) | |
H63 | 0.1384 | 0.2505 | 0.4634 | 0.058* | |
C64 | 0.0641 (4) | 0.29712 (18) | 0.6111 (4) | 0.0443 (8) | |
H64 | −0.0451 | 0.2856 | 0.6049 | 0.053* | |
C65 | 0.1114 (4) | 0.33474 (17) | 0.7053 (3) | 0.0375 (7) | |
H65 | 0.0353 | 0.3487 | 0.7636 | 0.045* | |
C66 | 0.2708 (3) | 0.35185 (14) | 0.7136 (3) | 0.0299 (5) | |
H66 | 0.3042 | 0.3772 | 0.7785 | 0.036* | |
C67 | 0.5548 (3) | 0.35279 (13) | 0.6308 (3) | 0.0284 (5) | |
H67 | 0.6158 | 0.3311 | 0.5655 | 0.034* | |
C68 | 0.6369 (4) | 0.34175 (17) | 0.7547 (3) | 0.0395 (7) | |
H68A | 0.7475 | 0.3563 | 0.7515 | 0.059* | |
H68B | 0.6374 | 0.2995 | 0.7722 | 0.059* | |
H68C | 0.5785 | 0.3624 | 0.8201 | 0.059* | |
N6 | 0.5620 (3) | 0.41681 (11) | 0.6017 (2) | 0.0242 (4) | |
H6A | 0.5020 | 0.4243 | 0.5331 | 0.036* | |
H6B | 0.6656 | 0.4274 | 0.5876 | 0.036* | |
H6C | 0.5227 | 0.4377 | 0.6667 | 0.036* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O11 | 0.0221 (8) | 0.0434 (12) | 0.0253 (9) | 0.0001 (8) | −0.0092 (7) | −0.0088 (8) |
O12 | 0.0177 (8) | 0.0418 (11) | 0.0182 (8) | 0.0051 (7) | −0.0033 (6) | −0.0027 (7) |
O13 | 0.0251 (9) | 0.0480 (12) | 0.0245 (9) | −0.0025 (9) | −0.0135 (7) | 0.0026 (9) |
O14 | 0.0169 (8) | 0.0512 (13) | 0.0214 (9) | −0.0070 (8) | 0.0005 (7) | −0.0036 (8) |
O15 | 0.0193 (8) | 0.0399 (10) | 0.0179 (8) | 0.0057 (8) | 0.0050 (6) | −0.0013 (7) |
O16 | 0.0193 (8) | 0.0532 (13) | 0.0123 (7) | −0.0065 (8) | 0.0028 (6) | 0.0039 (8) |
C11 | 0.0146 (9) | 0.0355 (12) | 0.0105 (9) | −0.0001 (9) | −0.0029 (7) | 0.0020 (8) |
C12 | 0.0138 (9) | 0.0318 (12) | 0.0124 (9) | −0.0005 (8) | −0.0014 (7) | −0.0001 (8) |
C13 | 0.0115 (9) | 0.0375 (13) | 0.0125 (9) | 0.0005 (8) | −0.0009 (7) | 0.0000 (8) |
C14 | 0.0144 (9) | 0.0357 (13) | 0.0165 (10) | 0.0015 (9) | −0.0031 (8) | −0.0051 (9) |
O21 | 0.0163 (8) | 0.0467 (12) | 0.0214 (9) | −0.0056 (7) | −0.0012 (7) | 0.0036 (8) |
O22 | 0.0239 (9) | 0.0487 (12) | 0.0215 (9) | −0.0013 (9) | 0.0115 (7) | −0.0013 (8) |
O23 | 0.0210 (8) | 0.0470 (12) | 0.0254 (9) | 0.0002 (8) | 0.0075 (7) | 0.0078 (9) |
O24 | 0.0160 (8) | 0.0453 (11) | 0.0187 (8) | 0.0051 (7) | 0.0027 (6) | 0.0015 (8) |
O25 | 0.0215 (8) | 0.0484 (12) | 0.0141 (8) | −0.0053 (8) | −0.0034 (6) | −0.0015 (7) |
O26 | 0.0181 (8) | 0.0443 (11) | 0.0175 (8) | 0.0053 (8) | −0.0050 (6) | 0.0015 (8) |
C21 | 0.0139 (9) | 0.0373 (13) | 0.0140 (10) | 0.0022 (9) | 0.0016 (8) | 0.0044 (9) |
C22 | 0.0118 (9) | 0.0391 (13) | 0.0122 (9) | −0.0002 (8) | 0.0008 (7) | 0.0012 (9) |
C23 | 0.0148 (9) | 0.0340 (12) | 0.0128 (9) | 0.0000 (9) | 0.0007 (7) | −0.0006 (9) |
C24 | 0.0137 (9) | 0.0402 (13) | 0.0118 (9) | −0.0013 (9) | 0.0013 (7) | −0.0024 (9) |
C31 | 0.0274 (13) | 0.0401 (16) | 0.0308 (14) | −0.0016 (11) | −0.0091 (11) | 0.0123 (12) |
C32 | 0.0357 (15) | 0.0466 (18) | 0.0339 (15) | −0.0011 (13) | −0.0035 (12) | 0.0081 (13) |
C33 | 0.0319 (16) | 0.066 (2) | 0.056 (2) | 0.0065 (16) | −0.0001 (15) | 0.0201 (19) |
C34 | 0.0330 (17) | 0.072 (3) | 0.079 (3) | −0.0013 (18) | −0.028 (2) | 0.024 (2) |
C35 | 0.073 (3) | 0.056 (2) | 0.063 (3) | 0.001 (2) | −0.046 (2) | 0.001 (2) |
C36 | 0.054 (2) | 0.049 (2) | 0.0372 (17) | 0.0129 (16) | −0.0156 (15) | 0.0048 (15) |
C37 | 0.0288 (14) | 0.059 (2) | 0.048 (2) | −0.0080 (14) | −0.0114 (14) | 0.0239 (17) |
C38 | 0.047 (2) | 0.056 (3) | 0.138 (6) | −0.007 (2) | −0.029 (3) | 0.011 (3) |
N3 | 0.0175 (9) | 0.0439 (13) | 0.0168 (9) | 0.0031 (9) | −0.0016 (7) | −0.0001 (9) |
C41 | 0.0309 (14) | 0.0331 (14) | 0.0366 (15) | −0.0045 (11) | 0.0027 (11) | −0.0070 (12) |
C42 | 0.061 (2) | 0.059 (2) | 0.0377 (18) | −0.0229 (19) | 0.0007 (17) | 0.0011 (16) |
C43 | 0.081 (3) | 0.079 (3) | 0.056 (3) | −0.046 (3) | 0.030 (3) | −0.013 (2) |
C44 | 0.041 (2) | 0.072 (3) | 0.080 (3) | −0.030 (2) | 0.022 (2) | −0.038 (3) |
C45 | 0.0316 (16) | 0.063 (3) | 0.071 (3) | −0.0060 (16) | −0.0057 (17) | −0.027 (2) |
C46 | 0.0290 (14) | 0.0455 (18) | 0.0470 (19) | −0.0030 (12) | −0.0024 (13) | −0.0057 (14) |
C47 | 0.0227 (12) | 0.0382 (15) | 0.0428 (17) | 0.0020 (11) | −0.0005 (11) | 0.0019 (13) |
C48 | 0.0407 (18) | 0.057 (2) | 0.068 (3) | 0.0023 (17) | 0.0136 (18) | −0.021 (2) |
N4 | 0.0155 (9) | 0.0393 (12) | 0.0191 (9) | −0.0027 (8) | −0.0017 (7) | −0.0028 (9) |
C51 | 0.0246 (12) | 0.0395 (14) | 0.0232 (12) | 0.0062 (11) | 0.0013 (10) | −0.0076 (11) |
C52 | 0.0425 (17) | 0.055 (2) | 0.0246 (14) | 0.0156 (15) | 0.0084 (12) | −0.0003 (13) |
C53 | 0.058 (2) | 0.064 (3) | 0.045 (2) | 0.011 (2) | 0.0290 (18) | −0.0002 (18) |
C54 | 0.0305 (16) | 0.073 (3) | 0.061 (2) | 0.0041 (17) | 0.0202 (16) | −0.018 (2) |
C55 | 0.0289 (15) | 0.062 (2) | 0.0478 (19) | 0.0134 (15) | −0.0028 (13) | −0.0133 (17) |
C56 | 0.0289 (13) | 0.0421 (16) | 0.0318 (14) | 0.0069 (12) | −0.0031 (11) | −0.0046 (12) |
C57 | 0.0217 (12) | 0.0458 (16) | 0.0286 (13) | 0.0016 (11) | −0.0024 (10) | −0.0111 (12) |
C58 | 0.0389 (18) | 0.049 (2) | 0.067 (3) | −0.0070 (15) | 0.0103 (18) | −0.0077 (19) |
N5 | 0.0176 (9) | 0.0411 (13) | 0.0172 (9) | 0.0047 (8) | 0.0003 (7) | 0.0007 (8) |
C61 | 0.0229 (11) | 0.0298 (12) | 0.0249 (12) | −0.0025 (9) | −0.0001 (9) | 0.0024 (10) |
C62 | 0.0402 (16) | 0.0428 (17) | 0.0319 (15) | −0.0052 (14) | −0.0009 (12) | −0.0054 (13) |
C63 | 0.050 (2) | 0.049 (2) | 0.046 (2) | −0.0162 (16) | −0.0181 (16) | −0.0024 (15) |
C64 | 0.0326 (15) | 0.052 (2) | 0.0484 (19) | −0.0163 (14) | −0.0117 (14) | 0.0125 (16) |
C65 | 0.0245 (13) | 0.0476 (18) | 0.0404 (16) | −0.0049 (12) | 0.0006 (12) | 0.0086 (14) |
C66 | 0.0215 (12) | 0.0381 (14) | 0.0301 (13) | −0.0021 (10) | 0.0004 (10) | 0.0000 (11) |
C67 | 0.0187 (11) | 0.0358 (14) | 0.0306 (13) | 0.0018 (10) | 0.0027 (9) | −0.0029 (11) |
C68 | 0.0262 (13) | 0.0483 (18) | 0.0440 (18) | 0.0022 (12) | −0.0099 (12) | 0.0127 (14) |
N6 | 0.0161 (9) | 0.0372 (12) | 0.0193 (9) | −0.0025 (8) | 0.0017 (7) | 0.0014 (8) |
O11—C11 | 1.251 (3) | C44—H44 | 0.95 |
O12—C11 | 1.262 (3) | C45—C46 | 1.392 (5) |
O13—C14 | 1.263 (3) | C45—H45 | 0.95 |
O14—C14 | 1.255 (3) | C46—H46 | 0.95 |
O15—C12 | 1.412 (3) | C47—N4 | 1.478 (4) |
O15—H15 | 0.84 | C47—C48 | 1.501 (5) |
O16—C13 | 1.419 (3) | C47—H47 | 1.00 |
O16—H16 | 0.84 | C48—H48A | 0.98 |
C11—C12 | 1.541 (3) | C48—H48B | 0.98 |
C12—C13 | 1.529 (3) | C48—H48C | 0.98 |
C12—H12 | 1.00 | N4—H4A | 0.91 |
C13—C14 | 1.535 (3) | N4—H4B | 0.91 |
C13—H13 | 1.00 | N4—H4C | 0.91 |
O21—C21 | 1.259 (3) | C51—C52 | 1.389 (5) |
O22—C21 | 1.258 (3) | C51—C56 | 1.390 (4) |
O23—C24 | 1.256 (3) | C51—C57 | 1.513 (4) |
O24—C24 | 1.253 (3) | C52—C53 | 1.393 (5) |
O25—C22 | 1.415 (3) | C52—H52 | 0.95 |
O25—H25 | 0.84 | C53—C54 | 1.374 (7) |
O26—C23 | 1.406 (3) | C53—H53 | 0.95 |
O26—H26 | 0.84 | C54—C55 | 1.381 (7) |
C21—C22 | 1.539 (3) | C54—H54 | 0.95 |
C22—C23 | 1.523 (3) | C55—C56 | 1.397 (5) |
C22—H22 | 1.00 | C55—H55 | 0.95 |
C23—C24 | 1.548 (3) | C56—H56 | 0.95 |
C23—H23 | 1.00 | C57—N5 | 1.504 (4) |
C31—C36 | 1.379 (5) | C57—C58 | 1.523 (6) |
C31—C32 | 1.382 (5) | C57—H57 | 1.00 |
C31—C37 | 1.513 (4) | C58—H58A | 0.98 |
C32—C33 | 1.396 (5) | C58—H58B | 0.98 |
C32—H32 | 0.95 | C58—H58C | 0.98 |
C33—C34 | 1.378 (7) | N5—H5A | 0.91 |
C33—H33 | 0.95 | N5—H5B | 0.91 |
C34—C35 | 1.373 (8) | N5—H5C | 0.91 |
C34—H34 | 0.95 | C61—C62 | 1.385 (4) |
C35—C36 | 1.393 (6) | C61—C66 | 1.395 (4) |
C35—H35 | 0.95 | C61—C67 | 1.516 (4) |
C36—H36 | 0.95 | C62—C63 | 1.400 (5) |
C37—C38 | 1.456 (7) | C62—H62 | 0.95 |
C37—N3 | 1.485 (4) | C63—C64 | 1.365 (6) |
C37—H37 | 1.00 | C63—H63 | 0.95 |
C38—H38A | 0.98 | C64—C65 | 1.387 (5) |
C38—H38B | 0.98 | C64—H64 | 0.95 |
C38—H38C | 0.98 | C65—C66 | 1.387 (4) |
N3—H3A | 0.91 | C65—H65 | 0.95 |
N3—H3B | 0.91 | C66—H66 | 0.95 |
N3—H3C | 0.91 | C67—N6 | 1.490 (4) |
C41—C46 | 1.379 (5) | C67—C68 | 1.525 (4) |
C41—C42 | 1.382 (5) | C67—H67 | 1.00 |
C41—C47 | 1.517 (4) | C68—H68A | 0.98 |
C42—C43 | 1.398 (6) | C68—H68B | 0.98 |
C42—H42 | 0.95 | C68—H68C | 0.98 |
C43—C44 | 1.341 (9) | N6—H6A | 0.91 |
C43—H43 | 0.95 | N6—H6B | 0.91 |
C44—C45 | 1.397 (8) | N6—H6C | 0.91 |
C12—O15—H15 | 109.5 | C41—C46—H46 | 119.6 |
C13—O16—H16 | 109.5 | C45—C46—H46 | 119.6 |
O11—C11—O12 | 124.5 (2) | N4—C47—C48 | 109.4 (3) |
O11—C11—C12 | 118.2 (2) | N4—C47—C41 | 110.3 (2) |
O12—C11—C12 | 117.3 (2) | C48—C47—C41 | 114.7 (3) |
O15—C12—C13 | 109.5 (2) | N4—C47—H47 | 107.4 |
O15—C12—C11 | 111.8 (2) | C48—C47—H47 | 107.4 |
C13—C12—C11 | 109.22 (18) | C41—C47—H47 | 107.4 |
O15—C12—H12 | 108.7 | C47—C48—H48A | 109.5 |
C13—C12—H12 | 108.7 | C47—C48—H48B | 109.5 |
C11—C12—H12 | 108.7 | H48A—C48—H48B | 109.5 |
O16—C13—C12 | 107.6 (2) | C47—C48—H48C | 109.5 |
O16—C13—C14 | 112.3 (2) | H48A—C48—H48C | 109.5 |
C12—C13—C14 | 112.09 (19) | H48B—C48—H48C | 109.5 |
O16—C13—H13 | 108.2 | C47—N4—H4A | 109.5 |
C12—C13—H13 | 108.2 | C47—N4—H4B | 109.5 |
C14—C13—H13 | 108.2 | H4A—N4—H4B | 109.5 |
O14—C14—O13 | 123.9 (2) | C47—N4—H4C | 109.5 |
O14—C14—C13 | 118.2 (2) | H4A—N4—H4C | 109.5 |
O13—C14—C13 | 117.8 (2) | H4B—N4—H4C | 109.5 |
C22—O25—H25 | 109.5 | C52—C51—C56 | 118.8 (3) |
C23—O26—H26 | 109.5 | C52—C51—C57 | 118.7 (3) |
O22—C21—O21 | 124.0 (2) | C56—C51—C57 | 122.2 (3) |
O22—C21—C22 | 118.2 (2) | C51—C52—C53 | 120.3 (3) |
O21—C21—C22 | 117.8 (2) | C51—C52—H52 | 119.9 |
O25—C22—C23 | 107.3 (2) | C53—C52—H52 | 119.9 |
O25—C22—C21 | 112.0 (2) | C54—C53—C52 | 120.7 (4) |
C23—C22—C21 | 113.43 (19) | C54—C53—H53 | 119.7 |
O25—C22—H22 | 108.0 | C52—C53—H53 | 119.7 |
C23—C22—H22 | 108.0 | C53—C54—C55 | 119.6 (3) |
C21—C22—H22 | 108.0 | C53—C54—H54 | 120.2 |
O26—C23—C22 | 110.1 (2) | C55—C54—H54 | 120.2 |
O26—C23—C24 | 112.0 (2) | C54—C55—C56 | 120.1 (4) |
C22—C23—C24 | 109.03 (18) | C54—C55—H55 | 119.9 |
O26—C23—H23 | 108.6 | C56—C55—H55 | 119.9 |
C22—C23—H23 | 108.6 | C51—C56—C55 | 120.4 (3) |
C24—C23—H23 | 108.6 | C51—C56—H56 | 119.8 |
O24—C24—O23 | 124.9 (2) | C55—C56—H56 | 119.8 |
O24—C24—C23 | 117.0 (2) | N5—C57—C51 | 108.5 (2) |
O23—C24—C23 | 118.0 (2) | N5—C57—C58 | 107.2 (3) |
C36—C31—C32 | 119.6 (3) | C51—C57—C58 | 116.2 (3) |
C36—C31—C37 | 118.2 (3) | N5—C57—H57 | 108.2 |
C32—C31—C37 | 122.1 (3) | C51—C57—H57 | 108.2 |
C31—C32—C33 | 119.6 (4) | C58—C57—H57 | 108.2 |
C31—C32—H32 | 120.2 | C57—C58—H58A | 109.5 |
C33—C32—H32 | 120.2 | C57—C58—H58B | 109.5 |
C34—C33—C32 | 120.7 (4) | H58A—C58—H58B | 109.5 |
C34—C33—H33 | 119.7 | C57—C58—H58C | 109.5 |
C32—C33—H33 | 119.7 | H58A—C58—H58C | 109.5 |
C35—C34—C33 | 119.4 (4) | H58B—C58—H58C | 109.5 |
C35—C34—H34 | 120.3 | C57—N5—H5A | 109.5 |
C33—C34—H34 | 120.3 | C57—N5—H5B | 109.5 |
C34—C35—C36 | 120.3 (4) | H5A—N5—H5B | 109.5 |
C34—C35—H35 | 119.9 | C57—N5—H5C | 109.5 |
C36—C35—H35 | 119.9 | H5A—N5—H5C | 109.5 |
C31—C36—C35 | 120.3 (4) | H5B—N5—H5C | 109.5 |
C31—C36—H36 | 119.8 | C62—C61—C66 | 119.4 (3) |
C35—C36—H36 | 119.8 | C62—C61—C67 | 119.6 (3) |
C38—C37—N3 | 110.3 (4) | C66—C61—C67 | 121.0 (3) |
C38—C37—C31 | 117.3 (4) | C61—C62—C63 | 120.0 (3) |
N3—C37—C31 | 109.3 (3) | C61—C62—H62 | 120.0 |
C38—C37—H37 | 106.4 | C63—C62—H62 | 120.0 |
N3—C37—H37 | 106.4 | C64—C63—C62 | 119.9 (3) |
C31—C37—H37 | 106.4 | C64—C63—H63 | 120.0 |
C37—C38—H38A | 109.5 | C62—C63—H63 | 120.0 |
C37—C38—H38B | 109.5 | C63—C64—C65 | 120.9 (3) |
H38A—C38—H38B | 109.5 | C63—C64—H64 | 119.5 |
C37—C38—H38C | 109.5 | C65—C64—H64 | 119.5 |
H38A—C38—H38C | 109.5 | C66—C65—C64 | 119.4 (3) |
H38B—C38—H38C | 109.5 | C66—C65—H65 | 120.3 |
C37—N3—H3A | 109.5 | C64—C65—H65 | 120.3 |
C37—N3—H3B | 109.5 | C65—C66—C61 | 120.3 (3) |
H3A—N3—H3B | 109.5 | C65—C66—H66 | 119.9 |
C37—N3—H3C | 109.5 | C61—C66—H66 | 119.9 |
H3A—N3—H3C | 109.5 | N6—C67—C61 | 109.8 (2) |
H3B—N3—H3C | 109.5 | N6—C67—C68 | 109.2 (3) |
C46—C41—C42 | 118.8 (3) | C61—C67—C68 | 113.3 (3) |
C46—C41—C47 | 122.1 (3) | N6—C67—H67 | 108.2 |
C42—C41—C47 | 119.1 (3) | C61—C67—H67 | 108.2 |
C41—C42—C43 | 120.2 (4) | C68—C67—H67 | 108.2 |
C41—C42—H42 | 119.9 | C67—C68—H68A | 109.5 |
C43—C42—H42 | 119.9 | C67—C68—H68B | 109.5 |
C44—C43—C42 | 120.7 (5) | H68A—C68—H68B | 109.5 |
C44—C43—H43 | 119.6 | C67—C68—H68C | 109.5 |
C42—C43—H43 | 119.6 | H68A—C68—H68C | 109.5 |
C43—C44—C45 | 120.2 (4) | H68B—C68—H68C | 109.5 |
C43—C44—H44 | 119.9 | C67—N6—H6A | 109.5 |
C45—C44—H44 | 119.9 | C67—N6—H6B | 109.5 |
C46—C45—C44 | 119.2 (4) | H6A—N6—H6B | 109.5 |
C46—C45—H45 | 120.4 | C67—N6—H6C | 109.5 |
C44—C45—H45 | 120.4 | H6A—N6—H6C | 109.5 |
C41—C46—C45 | 120.8 (4) | H6B—N6—H6C | 109.5 |
O11—C11—C12—O15 | −12.3 (3) | C46—C41—C42—C43 | −0.3 (6) |
O12—C11—C12—O15 | 169.8 (2) | C47—C41—C42—C43 | −179.1 (4) |
O11—C11—C12—C13 | −133.7 (2) | C41—C42—C43—C44 | 0.3 (8) |
O12—C11—C12—C13 | 48.4 (3) | C42—C43—C44—C45 | −0.2 (8) |
O15—C12—C13—O16 | −60.8 (2) | C43—C44—C45—C46 | 0.2 (7) |
C11—C12—C13—O16 | 62.0 (3) | C42—C41—C46—C45 | 0.3 (6) |
O15—C12—C13—C14 | 63.2 (3) | C47—C41—C46—C45 | 179.1 (3) |
C11—C12—C13—C14 | −174.0 (2) | C44—C45—C46—C41 | −0.2 (6) |
O16—C13—C14—O14 | 164.7 (2) | C46—C41—C47—N4 | −70.2 (4) |
C12—C13—C14—O14 | 43.4 (3) | C42—C41—C47—N4 | 108.6 (4) |
O16—C13—C14—O13 | −18.5 (3) | C46—C41—C47—C48 | 53.9 (5) |
C12—C13—C14—O13 | −139.9 (3) | C42—C41—C47—C48 | −127.3 (4) |
O22—C21—C22—O25 | −17.4 (3) | C56—C51—C52—C53 | −1.6 (5) |
O21—C21—C22—O25 | 165.9 (2) | C57—C51—C52—C53 | 173.0 (4) |
O22—C21—C22—C23 | −139.0 (3) | C51—C52—C53—C54 | 1.5 (7) |
O21—C21—C22—C23 | 44.3 (3) | C52—C53—C54—C55 | −0.1 (7) |
O25—C22—C23—O26 | −60.7 (2) | C53—C54—C55—C56 | −1.2 (6) |
C21—C22—C23—O26 | 63.5 (3) | C52—C51—C56—C55 | 0.2 (5) |
O25—C22—C23—C24 | 62.6 (3) | C57—C51—C56—C55 | −174.2 (3) |
C21—C22—C23—C24 | −173.2 (2) | C54—C55—C56—C51 | 1.2 (6) |
O26—C23—C24—O24 | 170.3 (2) | C52—C51—C57—N5 | −85.7 (3) |
C22—C23—C24—O24 | 48.3 (3) | C56—C51—C57—N5 | 88.7 (4) |
O26—C23—C24—O23 | −11.5 (3) | C52—C51—C57—C58 | 153.6 (3) |
C22—C23—C24—O23 | −133.5 (2) | C56—C51—C57—C58 | −32.0 (4) |
C36—C31—C32—C33 | 0.4 (5) | C66—C61—C62—C63 | 1.6 (5) |
C37—C31—C32—C33 | −175.9 (3) | C67—C61—C62—C63 | −176.8 (3) |
C31—C32—C33—C34 | 1.9 (6) | C61—C62—C63—C64 | −0.5 (6) |
C32—C33—C34—C35 | −2.2 (7) | C62—C63—C64—C65 | −0.5 (6) |
C33—C34—C35—C36 | 0.3 (7) | C63—C64—C65—C66 | 0.4 (6) |
C32—C31—C36—C35 | −2.3 (6) | C64—C65—C66—C61 | 0.7 (5) |
C37—C31—C36—C35 | 174.1 (4) | C62—C61—C66—C65 | −1.7 (5) |
C34—C35—C36—C31 | 2.0 (7) | C67—C61—C66—C65 | 176.7 (3) |
C36—C31—C37—C38 | 144.2 (5) | C62—C61—C67—N6 | 112.0 (3) |
C32—C31—C37—C38 | −39.5 (6) | C66—C61—C67—N6 | −66.4 (3) |
C36—C31—C37—N3 | −89.3 (4) | C62—C61—C67—C68 | −125.7 (3) |
C32—C31—C37—N3 | 87.0 (4) | C66—C61—C67—C68 | 55.9 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O15—H15···O22i | 0.84 | 1.91 | 2.743 (3) | 169 |
O16—H16···O23ii | 0.84 | 1.87 | 2.690 (3) | 164 |
O25—H25···O11 | 0.84 | 1.86 | 2.681 (3) | 167 |
O26—H26···O13iii | 0.84 | 1.91 | 2.743 (3) | 169 |
N3—H3A···O12 | 0.91 | 1.90 | 2.801 (3) | 171 |
N3—H3B···O22 | 0.91 | 1.82 | 2.718 (4) | 168 |
N3—H3C···O14iv | 0.91 | 1.89 | 2.777 (3) | 165 |
N4—H4A···O23v | 0.91 | 1.85 | 2.738 (3) | 165 |
N4—H4B···O12i | 0.91 | 1.92 | 2.825 (3) | 170 |
N4—H4C···O14 | 0.91 | 1.98 | 2.798 (3) | 149 |
N5—H5A···O21v | 0.91 | 1.89 | 2.774 (3) | 164 |
N5—H5B···O24ii | 0.91 | 1.89 | 2.798 (3) | 173 |
N5—H5C···O13 | 0.91 | 1.83 | 2.716 (3) | 164 |
N6—H6A···O24 | 0.91 | 1.95 | 2.847 (3) | 171 |
N6—H6B···O21i | 0.91 | 1.96 | 2.803 (3) | 154 |
N6—H6C···O11 | 0.91 | 1.86 | 2.747 (3) | 164 |
Symmetry codes: (i) x+1, y, z; (ii) x, y, z+1; (iii) x−1, y, z−1; (iv) x−1, y, z; (v) x+1, y, z+1. |
4(C8H12N)·2(C4H4O6)·CH4O | Z = 2 |
Mr = 816.93 | F(000) = 876 |
Triclinic, P1 | Dx = 1.267 Mg m−3 |
Hall symbol: P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.0822 (3) Å | Cell parameters from 9771 reflections |
b = 15.7819 (5) Å | θ = 2.6–27.6° |
c = 15.9040 (5) Å | µ = 0.09 mm−1 |
α = 108.7460 (15)° | T = 150 K |
β = 96.858 (2)° | Plate, colourless |
γ = 90.0600 (18)° | 0.20 × 0.16 × 0.08 mm |
V = 2141.33 (12) Å3 |
Kappa-CCD diffractometer | 9771 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 6899 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.094 |
ϕ scans, and ω scans with κ offsets | θmax = 27.6°, θmin = 2.6° |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | h = −11→11 |
Tmin = 0.975, Tmax = 0.993 | k = −20→17 |
28530 measured reflections | l = −19→20 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.051 | H-atom parameters constrained |
wR(F2) = 0.132 | w = 1/[σ2(Fo2) + (0.066P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
9771 reflections | Δρmax = 0.44 e Å−3 |
1074 parameters | Δρmin = −0.40 e Å−3 |
3 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0191 (18) |
4(C8H12N)·2(C4H4O6)·CH4O | γ = 90.0600 (18)° |
Mr = 816.93 | V = 2141.33 (12) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.0822 (3) Å | Mo Kα radiation |
b = 15.7819 (5) Å | µ = 0.09 mm−1 |
c = 15.9040 (5) Å | T = 150 K |
α = 108.7460 (15)° | 0.20 × 0.16 × 0.08 mm |
β = 96.858 (2)° |
Kappa-CCD diffractometer | 9771 independent reflections |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | 6899 reflections with I > 2σ(I) |
Tmin = 0.975, Tmax = 0.993 | Rint = 0.094 |
28530 measured reflections |
R[F2 > 2σ(F2)] = 0.051 | 3 restraints |
wR(F2) = 0.132 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.44 e Å−3 |
9771 reflections | Δρmin = −0.40 e Å−3 |
1074 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
O12 | −0.1286 (3) | 0.32807 (17) | 0.43058 (18) | 0.0309 (6) | |
O11 | 0.0193 (3) | 0.21248 (17) | 0.40497 (19) | 0.0305 (6) | |
O13 | 0.4229 (3) | 0.37649 (19) | 0.34477 (19) | 0.0373 (7) | |
O14 | 0.4236 (4) | 0.4723 (2) | 0.4833 (2) | 0.0473 (8) | |
O15 | 0.0711 (3) | 0.43776 (17) | 0.40486 (19) | 0.0302 (6) | |
H15 | 0.0292 | 0.4546 | 0.4515 | 0.045* | |
O16 | 0.2454 (3) | 0.36508 (17) | 0.53131 (17) | 0.0293 (6) | |
H16 | 0.3115 | 0.3414 | 0.5569 | 0.044* | |
C11 | −0.0084 (4) | 0.2922 (3) | 0.4104 (2) | 0.0259 (8) | |
C12 | 0.1113 (4) | 0.3475 (2) | 0.3882 (3) | 0.0260 (8) | |
H12D | 0.1191 | 0.3211 | 0.3228 | 0.031* | |
C13 | 0.2625 (4) | 0.3419 (3) | 0.4389 (3) | 0.0276 (8) | |
H13A | 0.2935 | 0.2785 | 0.4177 | 0.033* | |
C14 | 0.3806 (4) | 0.4019 (3) | 0.4216 (3) | 0.0312 (9) | |
O21 | 0.4854 (3) | 0.28847 (17) | 0.59234 (19) | 0.0328 (6) | |
O22 | 0.6239 (3) | 0.16811 (18) | 0.56818 (18) | 0.0315 (6) | |
O23 | 0.0848 (3) | 0.13457 (18) | 0.66674 (18) | 0.0312 (6) | |
O24 | 0.0449 (5) | 0.0494 (3) | 0.5243 (2) | 0.0709 (12) | |
O25 | 0.4190 (3) | 0.06888 (17) | 0.60625 (19) | 0.0317 (6) | |
H25 | 0.4599 | 0.0472 | 0.5597 | 0.048* | |
O26 | 0.2503 (3) | 0.13390 (18) | 0.47096 (17) | 0.0292 (6) | |
H26 | 0.1817 | 0.1536 | 0.4430 | 0.044* | |
C21 | 0.5070 (4) | 0.2087 (3) | 0.5888 (2) | 0.0270 (8) | |
C22 | 0.3844 (4) | 0.1587 (2) | 0.6159 (3) | 0.0266 (8) | |
H22A | 0.3771 | 0.1900 | 0.6807 | 0.032* | |
C23 | 0.2350 (4) | 0.1642 (2) | 0.5640 (2) | 0.0245 (8) | |
H23A | 0.2081 | 0.2284 | 0.5812 | 0.029* | |
C24 | 0.1128 (4) | 0.1106 (3) | 0.5867 (3) | 0.0294 (8) | |
O31 | 0.5630 (3) | 0.79291 (17) | 0.60979 (18) | 0.0304 (6) | |
O32 | 0.4034 (3) | 0.67865 (17) | 0.58923 (18) | 0.0297 (6) | |
O33 | 0.9854 (3) | 0.6271 (2) | 0.6763 (2) | 0.0394 (7) | |
O34 | 0.9327 (4) | 0.5333 (2) | 0.5377 (2) | 0.0477 (8) | |
O35 | 0.6137 (3) | 0.56940 (17) | 0.61649 (19) | 0.0306 (6) | |
H35 | 0.5567 | 0.5507 | 0.5681 | 0.046* | |
O36 | 0.7363 (3) | 0.64020 (18) | 0.48814 (17) | 0.0292 (6) | |
H36 | 0.7971 | 0.6585 | 0.4613 | 0.044* | |
C31 | 0.5313 (4) | 0.7143 (2) | 0.6074 (2) | 0.0257 (8) | |
C32 | 0.6613 (4) | 0.6601 (2) | 0.6317 (3) | 0.0268 (8) | |
H32A | 0.6958 | 0.6877 | 0.6971 | 0.032* | |
C33 | 0.7913 (4) | 0.6646 (3) | 0.5811 (3) | 0.0267 (8) | |
H33A | 0.8328 | 0.7277 | 0.6019 | 0.032* | |
C34 | 0.9147 (4) | 0.6032 (3) | 0.5990 (3) | 0.0310 (9) | |
O41 | 0.9463 (3) | 0.71289 (17) | 0.41826 (19) | 0.0317 (6) | |
O42 | 1.0950 (3) | 0.83235 (18) | 0.43839 (18) | 0.0302 (6) | |
O43 | 0.5133 (3) | 0.86458 (19) | 0.34099 (19) | 0.0348 (6) | |
O44 | 0.5368 (5) | 0.9517 (3) | 0.4810 (2) | 0.0829 (15) | |
O45 | 0.8738 (3) | 0.93122 (17) | 0.40015 (19) | 0.0319 (6) | |
H45 | 0.9348 | 0.9533 | 0.4464 | 0.048* | |
O46 | 0.7622 (3) | 0.86603 (18) | 0.53609 (17) | 0.0315 (6) | |
H46 | 0.7074 | 0.8445 | 0.5638 | 0.047* | |
C41 | 0.9695 (4) | 0.7924 (3) | 0.4192 (3) | 0.0273 (8) | |
C42 | 0.8350 (4) | 0.8415 (2) | 0.3916 (3) | 0.0253 (8) | |
H42A | 0.8010 | 0.8097 | 0.3269 | 0.030* | |
C43 | 0.7074 (4) | 0.8360 (3) | 0.4431 (3) | 0.0258 (8) | |
H43A | 0.6734 | 0.7717 | 0.4258 | 0.031* | |
C44 | 0.5759 (4) | 0.8889 (3) | 0.4201 (3) | 0.0306 (9) | |
N5 | 0.7932 (4) | 1.0526 (2) | 0.6477 (2) | 0.0302 (7) | |
H5A | 0.8883 | 1.0752 | 0.6575 | 0.045* | |
H5B | 0.7349 | 1.0819 | 0.6163 | 0.045* | |
H5C | 0.7905 | 0.9932 | 0.6158 | 0.045* | |
C51 | 0.8325 (4) | 1.0195 (3) | 0.7922 (3) | 0.0322 (9) | |
C52 | 0.9587 (5) | 1.0616 (3) | 0.8495 (3) | 0.0410 (10) | |
H52 | 0.9884 | 1.1203 | 0.8524 | 0.049* | |
C53 | 1.0416 (5) | 1.0196 (4) | 0.9023 (3) | 0.0508 (12) | |
H53 | 1.1275 | 1.0492 | 0.9407 | 0.061* | |
C54 | 0.9988 (6) | 0.9348 (4) | 0.8987 (3) | 0.0542 (13) | |
H54 | 1.0552 | 0.9060 | 0.9351 | 0.065* | |
C55 | 0.8754 (6) | 0.8916 (4) | 0.8431 (4) | 0.0549 (13) | |
H55 | 0.8469 | 0.8329 | 0.8410 | 0.066* | |
C56 | 0.7910 (5) | 0.9335 (3) | 0.7894 (3) | 0.0427 (10) | |
H56 | 0.7055 | 0.9033 | 0.7511 | 0.051* | |
C57 | 0.7368 (4) | 1.0653 (3) | 0.7365 (3) | 0.0314 (9) | |
H57 | 0.6348 | 1.0365 | 0.7236 | 0.038* | |
C58 | 0.7233 (5) | 1.1647 (3) | 0.7827 (3) | 0.0440 (11) | |
H58A | 0.6889 | 1.1742 | 0.8410 | 0.066* | |
H58B | 0.6518 | 1.1885 | 0.7457 | 0.066* | |
H58C | 0.8203 | 1.1955 | 0.7912 | 0.066* | |
N6 | 0.7723 (3) | 1.1132 (2) | 0.4118 (2) | 0.0279 (7) | |
H6A | 0.7806 | 1.0536 | 0.4025 | 0.042* | |
H6B | 0.7292 | 1.1385 | 0.4624 | 0.042* | |
H6C | 0.8641 | 1.1394 | 0.4181 | 0.042* | |
C61 | 0.7167 (4) | 1.0619 (3) | 0.2471 (3) | 0.0314 (9) | |
C62 | 0.6992 (4) | 0.9701 (3) | 0.2277 (3) | 0.0338 (9) | |
H62 | 0.6619 | 0.9472 | 0.2697 | 0.041* | |
C63 | 0.7353 (5) | 0.9109 (3) | 0.1476 (3) | 0.0388 (10) | |
H63 | 0.7252 | 0.8481 | 0.1358 | 0.047* | |
C64 | 0.7861 (5) | 0.9443 (3) | 0.0852 (3) | 0.0442 (11) | |
H64 | 0.8104 | 0.9042 | 0.0303 | 0.053* | |
C65 | 0.8017 (5) | 1.0358 (3) | 0.1024 (3) | 0.0455 (11) | |
H65 | 0.8357 | 1.0583 | 0.0592 | 0.055* | |
C66 | 0.7676 (5) | 1.0949 (3) | 0.1832 (3) | 0.0383 (10) | |
H66 | 0.7788 | 1.1576 | 0.1950 | 0.046* | |
C67 | 0.6783 (4) | 1.1269 (3) | 0.3333 (3) | 0.0343 (9) | |
H67 | 0.7018 | 1.1887 | 0.3331 | 0.041* | |
C68 | 0.5173 (5) | 1.1218 (3) | 0.3457 (3) | 0.0478 (11) | |
H68A | 0.4555 | 1.1318 | 0.2951 | 0.072* | |
H68B | 0.4993 | 1.1678 | 0.4014 | 0.072* | |
H68C | 0.4921 | 1.0625 | 0.3486 | 0.072* | |
N7 | 1.2288 (4) | 0.9470 (2) | 0.3590 (2) | 0.0300 (7) | |
H7A | 1.3211 | 0.9273 | 0.3484 | 0.045* | |
H7B | 1.1867 | 0.9146 | 0.3887 | 0.045* | |
H7C | 1.2359 | 1.0059 | 0.3929 | 0.045* | |
C71 | 1.1992 (4) | 0.9896 (3) | 0.2205 (3) | 0.0301 (8) | |
C72 | 1.3086 (5) | 0.9576 (3) | 0.1651 (3) | 0.0368 (9) | |
H72 | 1.3485 | 0.9009 | 0.1607 | 0.044* | |
C73 | 1.3597 (5) | 1.0075 (3) | 0.1167 (3) | 0.0423 (10) | |
H73 | 1.4348 | 0.9849 | 0.0796 | 0.051* | |
C74 | 1.3029 (5) | 1.0897 (3) | 0.1215 (3) | 0.0416 (10) | |
H74 | 1.3377 | 1.1233 | 0.0874 | 0.050* | |
C75 | 1.1952 (5) | 1.1228 (3) | 0.1763 (3) | 0.0422 (10) | |
H75 | 1.1565 | 1.1796 | 0.1804 | 0.051* | |
C76 | 1.1433 (5) | 1.0734 (3) | 0.2256 (3) | 0.0359 (9) | |
H76 | 1.0691 | 1.0967 | 0.2631 | 0.043* | |
C77 | 1.1343 (4) | 0.9359 (3) | 0.2716 (3) | 0.0323 (9) | |
H77 | 1.0350 | 0.9599 | 0.2856 | 0.039* | |
C78 | 1.1111 (5) | 0.8373 (3) | 0.2201 (3) | 0.0449 (11) | |
H78A | 1.0552 | 0.8294 | 0.1612 | 0.067* | |
H78B | 1.0554 | 0.8083 | 0.2532 | 0.067* | |
H78C | 1.2077 | 0.8101 | 0.2123 | 0.067* | |
N8 | 0.2635 (4) | 0.5499 (2) | 0.6500 (2) | 0.0302 (7) | |
H8A | 0.1742 | 0.5718 | 0.6651 | 0.045* | |
H8B | 0.2487 | 0.4970 | 0.6044 | 0.045* | |
H8C | 0.3136 | 0.5898 | 0.6323 | 0.045* | |
C81 | 0.3805 (4) | 0.6202 (3) | 0.8072 (3) | 0.0319 (8) | |
C82 | 0.2649 (5) | 0.6701 (3) | 0.8462 (3) | 0.0441 (10) | |
H82 | 0.1652 | 0.6545 | 0.8193 | 0.053* | |
C83 | 0.2955 (6) | 0.7427 (3) | 0.9242 (3) | 0.0545 (13) | |
H83 | 0.2167 | 0.7762 | 0.9510 | 0.065* | |
C84 | 0.4418 (6) | 0.7662 (3) | 0.9631 (3) | 0.0553 (13) | |
H84 | 0.4627 | 0.8150 | 1.0172 | 0.066* | |
C85 | 0.5558 (6) | 0.7188 (3) | 0.9233 (3) | 0.0562 (13) | |
H85 | 0.6556 | 0.7356 | 0.9492 | 0.067* | |
C86 | 0.5256 (5) | 0.6464 (3) | 0.8454 (3) | 0.0440 (11) | |
H86 | 0.6052 | 0.6145 | 0.8179 | 0.053* | |
C87 | 0.3522 (4) | 0.5351 (3) | 0.7295 (3) | 0.0303 (8) | |
H87 | 0.4506 | 0.5127 | 0.7116 | 0.036* | |
C88 | 0.2734 (5) | 0.4620 (3) | 0.7542 (3) | 0.0366 (9) | |
H88A | 0.3361 | 0.4476 | 0.8019 | 0.055* | |
H88B | 0.2549 | 0.4082 | 0.7015 | 0.055* | |
H88C | 0.1787 | 0.4835 | 0.7750 | 0.055* | |
N9 | 0.1975 (4) | 0.6085 (2) | 0.4275 (2) | 0.0297 (7) | |
H9A | 0.1218 | 0.6438 | 0.4190 | 0.045* | |
H9B | 0.2498 | 0.6345 | 0.4825 | 0.045* | |
H9C | 0.1599 | 0.5538 | 0.4239 | 0.045* | |
C91 | 0.2154 (4) | 0.5588 (3) | 0.2637 (3) | 0.0312 (9) | |
C92 | 0.1000 (5) | 0.6014 (3) | 0.2300 (3) | 0.0410 (10) | |
H92 | 0.0627 | 0.6538 | 0.2688 | 0.049* | |
C93 | 0.0389 (6) | 0.5691 (3) | 0.1415 (3) | 0.0510 (12) | |
H93 | −0.0397 | 0.5993 | 0.1199 | 0.061* | |
C94 | 0.0917 (6) | 0.4929 (3) | 0.0843 (3) | 0.0529 (12) | |
H94 | 0.0508 | 0.4712 | 0.0230 | 0.063* | |
C95 | 0.2040 (5) | 0.4484 (3) | 0.1164 (3) | 0.0487 (12) | |
H95 | 0.2410 | 0.3962 | 0.0772 | 0.058* | |
C96 | 0.2628 (4) | 0.4798 (3) | 0.2057 (3) | 0.0379 (10) | |
H96 | 0.3366 | 0.4471 | 0.2278 | 0.045* | |
C97 | 0.2989 (4) | 0.5977 (3) | 0.3563 (3) | 0.0297 (8) | |
H97 | 0.3782 | 0.5561 | 0.3644 | 0.036* | |
C98 | 0.3717 (4) | 0.6887 (3) | 0.3692 (3) | 0.0323 (9) | |
H98A | 0.4420 | 0.6821 | 0.3255 | 0.049* | |
H98B | 0.4248 | 0.7125 | 0.4299 | 0.049* | |
H98C | 0.2954 | 0.7299 | 0.3605 | 0.049* | |
N10 | 0.7098 (4) | 0.4554 (2) | 0.3678 (2) | 0.0288 (7) | |
H10A | 0.7144 | 0.5074 | 0.4145 | 0.043* | |
H10B | 0.7664 | 0.4145 | 0.3843 | 0.043* | |
H10C | 0.6140 | 0.4339 | 0.3519 | 0.043* | |
C101 | 0.7631 (4) | 0.3867 (3) | 0.2105 (3) | 0.0329 (9) | |
C102 | 0.6311 (5) | 0.3389 (3) | 0.1696 (3) | 0.0479 (11) | |
H102 | 0.5418 | 0.3551 | 0.1952 | 0.058* | |
C103 | 0.6301 (6) | 0.2670 (3) | 0.0906 (3) | 0.0560 (13) | |
H103 | 0.5397 | 0.2344 | 0.0625 | 0.067* | |
C104 | 0.7591 (6) | 0.2428 (3) | 0.0530 (3) | 0.0513 (12) | |
H104 | 0.7573 | 0.1947 | −0.0016 | 0.062* | |
C105 | 0.8908 (6) | 0.2887 (3) | 0.0952 (3) | 0.0530 (12) | |
H105 | 0.9805 | 0.2712 | 0.0704 | 0.064* | |
C106 | 0.8927 (5) | 0.3605 (3) | 0.1740 (3) | 0.0422 (10) | |
H106 | 0.9839 | 0.3917 | 0.2028 | 0.051* | |
C107 | 0.7667 (4) | 0.4725 (3) | 0.2900 (3) | 0.0298 (8) | |
H107 | 0.8725 | 0.4949 | 0.3088 | 0.036* | |
C108 | 0.6793 (5) | 0.5453 (3) | 0.2653 (3) | 0.0373 (9) | |
H10D | 0.5756 | 0.5242 | 0.2448 | 0.056* | |
H10E | 0.7222 | 0.5593 | 0.2174 | 0.056* | |
H10F | 0.6838 | 0.5992 | 0.3179 | 0.056* | |
N11 | 0.3122 (4) | −0.1098 (2) | 0.5935 (2) | 0.0292 (7) | |
H11A | 0.2482 | −0.1340 | 0.5426 | 0.044* | |
H11B | 0.3997 | −0.1379 | 0.5878 | 0.044* | |
H11C | 0.3286 | −0.0504 | 0.6026 | 0.044* | |
C111 | 0.3322 (5) | −0.0623 (3) | 0.7581 (3) | 0.0335 (9) | |
C112 | 0.3330 (5) | 0.0309 (3) | 0.7847 (3) | 0.0395 (10) | |
H112 | 0.2780 | 0.0593 | 0.7475 | 0.047* | |
C113 | 0.4122 (5) | 0.0826 (3) | 0.8643 (3) | 0.0404 (10) | |
H113 | 0.4114 | 0.1460 | 0.8813 | 0.049* | |
C114 | 0.4926 (5) | 0.0425 (3) | 0.9191 (3) | 0.0419 (10) | |
H114 | 0.5476 | 0.0780 | 0.9737 | 0.050* | |
C115 | 0.4923 (5) | −0.0502 (3) | 0.8937 (3) | 0.0458 (11) | |
H115 | 0.5472 | −0.0781 | 0.9315 | 0.055* | |
C116 | 0.4133 (5) | −0.1025 (3) | 0.8142 (3) | 0.0395 (10) | |
H116 | 0.4141 | −0.1659 | 0.7977 | 0.047* | |
C117 | 0.2462 (5) | −0.1215 (3) | 0.6721 (3) | 0.0391 (10) | |
H117 | 0.2586 | −0.1850 | 0.6701 | 0.047* | |
C118 | 0.0870 (5) | −0.1064 (4) | 0.6636 (3) | 0.0528 (12) | |
H11D | 0.0470 | −0.1080 | 0.7176 | 0.079* | |
H11E | 0.0366 | −0.1532 | 0.6114 | 0.079* | |
H11F | 0.0708 | −0.0477 | 0.6560 | 0.079* | |
N12 | 0.7332 (3) | 0.3980 (2) | 0.5934 (2) | 0.0295 (7) | |
H12A | 0.6605 | 0.3603 | 0.5974 | 0.044* | |
H12B | 0.7678 | 0.3755 | 0.5395 | 0.044* | |
H12C | 0.6956 | 0.4527 | 0.5986 | 0.044* | |
C121 | 0.8077 (5) | 0.4427 (3) | 0.7591 (3) | 0.0341 (9) | |
C122 | 0.7022 (5) | 0.3963 (3) | 0.7861 (3) | 0.0448 (11) | |
H122 | 0.6525 | 0.3440 | 0.7443 | 0.054* | |
C123 | 0.6689 (6) | 0.4259 (4) | 0.8738 (4) | 0.0577 (13) | |
H123 | 0.5967 | 0.3939 | 0.8916 | 0.069* | |
C124 | 0.7402 (6) | 0.5012 (4) | 0.9342 (4) | 0.0597 (15) | |
H124 | 0.7190 | 0.5205 | 0.9944 | 0.072* | |
C125 | 0.8429 (6) | 0.5494 (4) | 0.9084 (3) | 0.0580 (14) | |
H125 | 0.8906 | 0.6022 | 0.9505 | 0.070* | |
C126 | 0.8765 (5) | 0.5210 (3) | 0.8215 (3) | 0.0441 (10) | |
H126 | 0.9465 | 0.5547 | 0.8039 | 0.053* | |
C127 | 0.8584 (4) | 0.4074 (3) | 0.6675 (3) | 0.0299 (8) | |
H127 | 0.9347 | 0.4511 | 0.6633 | 0.036* | |
C128 | 0.9282 (4) | 0.3173 (3) | 0.6511 (3) | 0.0367 (9) | |
H12E | 1.0124 | 0.3222 | 0.6973 | 0.055* | |
H12F | 0.9630 | 0.2985 | 0.5920 | 0.055* | |
H12G | 0.8545 | 0.2729 | 0.6532 | 0.055* | |
O1 | 0.2387 (6) | 0.2634 (3) | 0.8082 (3) | 0.0857 (13) | |
H1 | 0.1817 | 0.2267 | 0.7671 | 0.129* | |
C1 | 0.1652 (10) | 0.3027 (6) | 0.8748 (5) | 0.109 (3) | |
H1A | 0.2212 | 0.3569 | 0.9143 | 0.164* | |
H1B | 0.1510 | 0.2618 | 0.9086 | 0.164* | |
H1C | 0.0683 | 0.3190 | 0.8517 | 0.164* | |
O2 | 0.5884 (5) | 0.7303 (3) | 0.1910 (3) | 0.0862 (14) | |
H2 | 0.5541 | 0.7735 | 0.2289 | 0.129* | |
C2 | 0.4731 (12) | 0.6745 (6) | 0.1372 (6) | 0.115 (3) | |
H2A | 0.4381 | 0.6355 | 0.1685 | 0.173* | |
H2B | 0.5078 | 0.6378 | 0.0814 | 0.173* | |
H2C | 0.3916 | 0.7106 | 0.1237 | 0.173* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O12 | 0.0239 (14) | 0.0272 (14) | 0.0409 (16) | 0.0028 (11) | 0.0060 (11) | 0.0093 (12) |
O11 | 0.0237 (13) | 0.0246 (15) | 0.0435 (16) | 0.0023 (11) | 0.0047 (12) | 0.0113 (12) |
O13 | 0.0316 (15) | 0.0381 (17) | 0.0410 (17) | −0.0022 (12) | 0.0089 (13) | 0.0097 (13) |
O14 | 0.0499 (19) | 0.0361 (18) | 0.0464 (19) | −0.0219 (14) | 0.0033 (15) | 0.0015 (15) |
O15 | 0.0243 (14) | 0.0279 (14) | 0.0421 (17) | 0.0045 (11) | 0.0085 (12) | 0.0149 (13) |
O16 | 0.0302 (15) | 0.0262 (14) | 0.0323 (15) | 0.0011 (11) | 0.0028 (11) | 0.0109 (12) |
C11 | 0.0246 (19) | 0.025 (2) | 0.027 (2) | 0.0008 (15) | 0.0008 (15) | 0.0084 (15) |
C12 | 0.0193 (18) | 0.0232 (19) | 0.036 (2) | 0.0015 (14) | 0.0052 (15) | 0.0092 (16) |
C13 | 0.0239 (19) | 0.0233 (19) | 0.033 (2) | 0.0024 (15) | 0.0055 (16) | 0.0050 (16) |
C14 | 0.0212 (19) | 0.030 (2) | 0.047 (3) | 0.0021 (15) | 0.0041 (17) | 0.019 (2) |
O21 | 0.0283 (14) | 0.0235 (15) | 0.0466 (17) | −0.0030 (11) | −0.0025 (12) | 0.0137 (12) |
O22 | 0.0254 (14) | 0.0356 (15) | 0.0372 (15) | 0.0045 (11) | 0.0068 (11) | 0.0159 (13) |
O23 | 0.0292 (15) | 0.0315 (15) | 0.0332 (16) | 0.0010 (11) | 0.0093 (12) | 0.0088 (12) |
O24 | 0.084 (3) | 0.073 (3) | 0.043 (2) | −0.053 (2) | 0.0091 (19) | 0.0012 (18) |
O25 | 0.0324 (15) | 0.0243 (14) | 0.0415 (17) | 0.0038 (11) | 0.0085 (12) | 0.0138 (12) |
O26 | 0.0259 (14) | 0.0346 (15) | 0.0269 (14) | 0.0025 (11) | 0.0008 (11) | 0.0107 (12) |
C21 | 0.0218 (19) | 0.032 (2) | 0.0252 (19) | −0.0023 (15) | −0.0017 (14) | 0.0087 (16) |
C22 | 0.029 (2) | 0.0191 (18) | 0.030 (2) | 0.0035 (15) | 0.0023 (16) | 0.0061 (15) |
C23 | 0.0206 (18) | 0.0231 (19) | 0.030 (2) | 0.0011 (14) | 0.0020 (15) | 0.0091 (16) |
C24 | 0.0259 (19) | 0.025 (2) | 0.033 (2) | −0.0020 (15) | −0.0006 (16) | 0.0063 (17) |
O31 | 0.0260 (14) | 0.0232 (14) | 0.0432 (16) | 0.0020 (10) | 0.0057 (12) | 0.0120 (12) |
O32 | 0.0261 (14) | 0.0242 (14) | 0.0386 (15) | −0.0003 (11) | 0.0024 (12) | 0.0103 (12) |
O33 | 0.0325 (16) | 0.0440 (18) | 0.0383 (17) | 0.0071 (13) | −0.0038 (13) | 0.0115 (14) |
O34 | 0.0496 (19) | 0.0384 (18) | 0.0453 (18) | 0.0191 (14) | 0.0012 (14) | 0.0014 (14) |
O35 | 0.0268 (14) | 0.0231 (14) | 0.0422 (17) | −0.0006 (11) | 0.0012 (12) | 0.0121 (12) |
O36 | 0.0261 (14) | 0.0313 (15) | 0.0304 (15) | −0.0006 (11) | 0.0024 (11) | 0.0107 (12) |
C31 | 0.0238 (19) | 0.025 (2) | 0.029 (2) | 0.0032 (15) | 0.0063 (15) | 0.0095 (16) |
C32 | 0.0200 (18) | 0.027 (2) | 0.033 (2) | 0.0007 (15) | 0.0019 (15) | 0.0098 (16) |
C33 | 0.0217 (18) | 0.0224 (19) | 0.034 (2) | −0.0007 (14) | −0.0004 (15) | 0.0071 (16) |
C34 | 0.0233 (19) | 0.025 (2) | 0.046 (2) | 0.0023 (15) | 0.0044 (17) | 0.0121 (18) |
O41 | 0.0285 (14) | 0.0252 (15) | 0.0425 (16) | 0.0039 (11) | 0.0067 (12) | 0.0116 (12) |
O42 | 0.0207 (13) | 0.0354 (15) | 0.0348 (15) | 0.0006 (11) | 0.0022 (11) | 0.0121 (12) |
O43 | 0.0264 (14) | 0.0358 (16) | 0.0433 (17) | 0.0048 (11) | 0.0003 (12) | 0.0159 (13) |
O44 | 0.099 (3) | 0.080 (3) | 0.046 (2) | 0.067 (3) | −0.005 (2) | −0.0083 (19) |
O45 | 0.0286 (15) | 0.0247 (14) | 0.0439 (17) | −0.0010 (11) | −0.0025 (12) | 0.0156 (13) |
O46 | 0.0297 (15) | 0.0344 (15) | 0.0317 (15) | −0.0010 (12) | 0.0036 (12) | 0.0124 (12) |
C41 | 0.0231 (19) | 0.027 (2) | 0.030 (2) | 0.0014 (15) | 0.0045 (16) | 0.0070 (16) |
C42 | 0.027 (2) | 0.0185 (18) | 0.030 (2) | −0.0011 (14) | 0.0014 (15) | 0.0083 (15) |
C43 | 0.0218 (18) | 0.025 (2) | 0.031 (2) | 0.0027 (14) | 0.0038 (15) | 0.0092 (16) |
C44 | 0.028 (2) | 0.030 (2) | 0.034 (2) | 0.0033 (15) | 0.0036 (17) | 0.0103 (18) |
N5 | 0.0271 (17) | 0.0324 (18) | 0.0318 (18) | 0.0016 (13) | 0.0019 (14) | 0.0119 (15) |
C51 | 0.029 (2) | 0.038 (2) | 0.030 (2) | 0.0014 (16) | 0.0066 (16) | 0.0094 (17) |
C52 | 0.032 (2) | 0.050 (3) | 0.040 (2) | 0.0007 (18) | 0.0024 (19) | 0.014 (2) |
C53 | 0.037 (2) | 0.077 (4) | 0.042 (3) | 0.009 (2) | 0.004 (2) | 0.025 (3) |
C54 | 0.049 (3) | 0.080 (4) | 0.048 (3) | 0.021 (3) | 0.010 (2) | 0.039 (3) |
C55 | 0.064 (3) | 0.057 (3) | 0.060 (3) | 0.013 (2) | 0.022 (3) | 0.036 (3) |
C56 | 0.041 (2) | 0.046 (3) | 0.045 (3) | 0.0027 (19) | 0.011 (2) | 0.019 (2) |
C57 | 0.0241 (19) | 0.039 (2) | 0.031 (2) | 0.0008 (16) | 0.0030 (15) | 0.0114 (18) |
C58 | 0.050 (3) | 0.045 (3) | 0.038 (2) | 0.016 (2) | 0.008 (2) | 0.013 (2) |
N6 | 0.0242 (16) | 0.0269 (17) | 0.0293 (17) | 0.0012 (13) | 0.0019 (13) | 0.0049 (14) |
C61 | 0.0224 (19) | 0.041 (2) | 0.030 (2) | 0.0033 (16) | 0.0005 (15) | 0.0112 (18) |
C62 | 0.031 (2) | 0.038 (2) | 0.033 (2) | 0.0017 (16) | 0.0045 (16) | 0.0122 (18) |
C63 | 0.035 (2) | 0.042 (2) | 0.037 (2) | 0.0034 (18) | −0.0020 (18) | 0.0114 (19) |
C64 | 0.040 (2) | 0.054 (3) | 0.032 (2) | 0.005 (2) | 0.0087 (18) | 0.003 (2) |
C65 | 0.041 (3) | 0.064 (3) | 0.036 (2) | −0.003 (2) | 0.013 (2) | 0.019 (2) |
C66 | 0.035 (2) | 0.041 (2) | 0.039 (2) | −0.0032 (18) | 0.0013 (18) | 0.014 (2) |
C67 | 0.032 (2) | 0.039 (2) | 0.033 (2) | 0.0056 (17) | 0.0028 (17) | 0.0132 (18) |
C68 | 0.033 (2) | 0.066 (3) | 0.039 (2) | 0.007 (2) | 0.0031 (19) | 0.010 (2) |
N7 | 0.0268 (17) | 0.0302 (18) | 0.0336 (18) | 0.0019 (13) | 0.0037 (14) | 0.0111 (15) |
C71 | 0.0274 (19) | 0.031 (2) | 0.031 (2) | 0.0007 (15) | 0.0036 (15) | 0.0084 (17) |
C72 | 0.035 (2) | 0.036 (2) | 0.043 (2) | 0.0083 (17) | 0.0128 (18) | 0.0149 (19) |
C73 | 0.047 (3) | 0.045 (3) | 0.036 (2) | 0.002 (2) | 0.012 (2) | 0.011 (2) |
C74 | 0.040 (2) | 0.050 (3) | 0.040 (2) | 0.0008 (19) | 0.0012 (19) | 0.023 (2) |
C75 | 0.048 (3) | 0.037 (2) | 0.046 (3) | 0.0104 (19) | 0.004 (2) | 0.020 (2) |
C76 | 0.033 (2) | 0.038 (2) | 0.035 (2) | 0.0073 (17) | 0.0040 (17) | 0.0103 (18) |
C77 | 0.027 (2) | 0.037 (2) | 0.033 (2) | 0.0013 (16) | 0.0034 (16) | 0.0112 (18) |
C78 | 0.051 (3) | 0.039 (3) | 0.042 (3) | −0.010 (2) | 0.000 (2) | 0.012 (2) |
N8 | 0.0253 (17) | 0.0313 (18) | 0.0349 (18) | 0.0003 (13) | 0.0007 (14) | 0.0131 (15) |
C81 | 0.033 (2) | 0.032 (2) | 0.031 (2) | 0.0017 (16) | 0.0023 (16) | 0.0119 (17) |
C82 | 0.041 (2) | 0.038 (2) | 0.045 (3) | 0.0026 (19) | 0.001 (2) | 0.004 (2) |
C83 | 0.060 (3) | 0.045 (3) | 0.047 (3) | 0.012 (2) | 0.004 (2) | 0.000 (2) |
C84 | 0.072 (4) | 0.041 (3) | 0.045 (3) | 0.001 (2) | −0.005 (2) | 0.006 (2) |
C85 | 0.052 (3) | 0.046 (3) | 0.056 (3) | −0.003 (2) | −0.016 (2) | 0.006 (2) |
C86 | 0.032 (2) | 0.045 (3) | 0.047 (3) | −0.0014 (18) | −0.0031 (19) | 0.006 (2) |
C87 | 0.0262 (19) | 0.031 (2) | 0.036 (2) | 0.0041 (16) | 0.0007 (16) | 0.0144 (17) |
C88 | 0.039 (2) | 0.032 (2) | 0.039 (2) | −0.0014 (17) | 0.0037 (18) | 0.0127 (18) |
N9 | 0.0261 (17) | 0.0283 (17) | 0.0350 (18) | −0.0010 (13) | 0.0015 (14) | 0.0115 (14) |
C91 | 0.026 (2) | 0.033 (2) | 0.037 (2) | −0.0005 (16) | 0.0034 (16) | 0.0142 (18) |
C92 | 0.041 (2) | 0.041 (3) | 0.038 (2) | 0.0058 (19) | 0.0007 (19) | 0.010 (2) |
C93 | 0.054 (3) | 0.054 (3) | 0.044 (3) | 0.015 (2) | 0.000 (2) | 0.017 (2) |
C94 | 0.059 (3) | 0.055 (3) | 0.038 (3) | 0.002 (2) | −0.003 (2) | 0.009 (2) |
C95 | 0.041 (3) | 0.047 (3) | 0.047 (3) | 0.006 (2) | 0.006 (2) | −0.001 (2) |
C96 | 0.030 (2) | 0.037 (2) | 0.042 (2) | 0.0043 (17) | 0.0023 (18) | 0.0075 (19) |
C97 | 0.0224 (19) | 0.033 (2) | 0.036 (2) | 0.0048 (15) | 0.0044 (15) | 0.0144 (17) |
C98 | 0.0264 (19) | 0.030 (2) | 0.042 (2) | −0.0022 (15) | 0.0045 (17) | 0.0125 (18) |
N10 | 0.0267 (17) | 0.0280 (18) | 0.0320 (18) | 0.0009 (13) | 0.0029 (13) | 0.0103 (14) |
C101 | 0.033 (2) | 0.030 (2) | 0.037 (2) | 0.0036 (16) | 0.0064 (17) | 0.0124 (18) |
C102 | 0.036 (2) | 0.041 (3) | 0.057 (3) | 0.0024 (19) | 0.007 (2) | 0.001 (2) |
C103 | 0.055 (3) | 0.049 (3) | 0.050 (3) | 0.000 (2) | 0.000 (2) | 0.000 (2) |
C104 | 0.074 (4) | 0.039 (3) | 0.034 (2) | 0.005 (2) | 0.011 (2) | 0.001 (2) |
C105 | 0.059 (3) | 0.054 (3) | 0.047 (3) | 0.011 (2) | 0.026 (2) | 0.010 (2) |
C106 | 0.035 (2) | 0.045 (3) | 0.043 (3) | 0.0019 (19) | 0.0078 (19) | 0.008 (2) |
C107 | 0.0270 (19) | 0.028 (2) | 0.034 (2) | −0.0026 (15) | 0.0042 (16) | 0.0097 (17) |
C108 | 0.039 (2) | 0.036 (2) | 0.039 (2) | 0.0032 (17) | 0.0015 (18) | 0.0143 (19) |
N11 | 0.0274 (17) | 0.0300 (18) | 0.0295 (17) | 0.0005 (13) | 0.0011 (13) | 0.0095 (14) |
C111 | 0.032 (2) | 0.037 (2) | 0.030 (2) | −0.0040 (17) | 0.0057 (17) | 0.0093 (18) |
C112 | 0.035 (2) | 0.048 (3) | 0.038 (2) | 0.0011 (18) | 0.0057 (18) | 0.018 (2) |
C113 | 0.044 (2) | 0.032 (2) | 0.042 (3) | −0.0044 (18) | 0.009 (2) | 0.0069 (19) |
C114 | 0.045 (3) | 0.042 (3) | 0.032 (2) | −0.0092 (19) | 0.0053 (19) | 0.0018 (19) |
C115 | 0.042 (3) | 0.055 (3) | 0.039 (3) | 0.003 (2) | 0.003 (2) | 0.014 (2) |
C116 | 0.042 (2) | 0.037 (2) | 0.038 (2) | 0.0011 (19) | 0.0085 (19) | 0.009 (2) |
C117 | 0.034 (2) | 0.051 (3) | 0.031 (2) | −0.0120 (19) | 0.0035 (17) | 0.0115 (19) |
C118 | 0.038 (3) | 0.068 (3) | 0.047 (3) | 0.002 (2) | 0.003 (2) | 0.013 (2) |
N12 | 0.0240 (17) | 0.0291 (17) | 0.0365 (18) | 0.0036 (13) | 0.0040 (14) | 0.0122 (14) |
C121 | 0.033 (2) | 0.030 (2) | 0.038 (2) | 0.0060 (17) | −0.0002 (18) | 0.0091 (18) |
C122 | 0.048 (3) | 0.047 (3) | 0.041 (3) | 0.000 (2) | 0.010 (2) | 0.015 (2) |
C123 | 0.059 (3) | 0.074 (4) | 0.049 (3) | 0.006 (3) | 0.011 (3) | 0.030 (3) |
C124 | 0.059 (3) | 0.081 (4) | 0.038 (3) | 0.019 (3) | 0.007 (2) | 0.017 (3) |
C125 | 0.056 (3) | 0.062 (3) | 0.040 (3) | 0.012 (3) | −0.006 (2) | −0.001 (2) |
C126 | 0.036 (2) | 0.039 (2) | 0.047 (3) | 0.0040 (18) | −0.0054 (19) | 0.003 (2) |
C127 | 0.0212 (18) | 0.028 (2) | 0.039 (2) | −0.0012 (14) | 0.0005 (16) | 0.0107 (17) |
C128 | 0.028 (2) | 0.033 (2) | 0.052 (3) | 0.0049 (16) | 0.0050 (18) | 0.0171 (19) |
O1 | 0.095 (3) | 0.065 (3) | 0.073 (3) | 0.004 (2) | −0.004 (3) | −0.006 (2) |
C1 | 0.124 (7) | 0.132 (7) | 0.082 (5) | 0.002 (6) | 0.036 (5) | 0.040 (5) |
O2 | 0.084 (3) | 0.071 (3) | 0.085 (3) | −0.022 (2) | 0.024 (3) | −0.005 (2) |
C2 | 0.149 (8) | 0.121 (7) | 0.095 (6) | 0.027 (6) | 0.021 (6) | 0.060 (6) |
O12—C11 | 1.259 (4) | N8—C87 | 1.499 (5) |
O11—C11 | 1.261 (5) | N8—H8A | 0.91 |
O13—C14 | 1.265 (5) | N8—H8B | 0.91 |
O14—C14 | 1.249 (5) | N8—H8C | 0.91 |
O15—C12 | 1.420 (4) | C81—C86 | 1.387 (6) |
O15—H15 | 0.84 | C81—C82 | 1.397 (6) |
O16—C13 | 1.424 (5) | C81—C87 | 1.502 (6) |
O16—H16 | 0.84 | C82—C83 | 1.390 (6) |
C11—C12 | 1.534 (5) | C82—H82 | 0.95 |
C12—C13 | 1.525 (5) | C83—C84 | 1.394 (7) |
C12—H12D | 1.00 | C83—H83 | 0.95 |
C13—C14 | 1.535 (5) | C84—C85 | 1.374 (7) |
C13—H13A | 1.00 | C84—H84 | 0.95 |
O21—C21 | 1.259 (5) | C85—C86 | 1.386 (7) |
O22—C21 | 1.263 (5) | C85—H85 | 0.95 |
O23—C24 | 1.264 (5) | C86—H86 | 0.95 |
O24—C24 | 1.238 (5) | C87—C88 | 1.535 (6) |
O25—C22 | 1.416 (4) | C87—H87 | 1.00 |
O25—H25 | 0.84 | C88—H88A | 0.98 |
O26—C23 | 1.426 (4) | C88—H88B | 0.98 |
O26—H26 | 0.84 | C88—H88C | 0.98 |
C21—C22 | 1.543 (5) | N9—C97 | 1.511 (5) |
C22—C23 | 1.519 (5) | N9—H9A | 0.91 |
C22—H22A | 1.00 | N9—H9B | 0.91 |
C23—C24 | 1.539 (5) | N9—H9C | 0.91 |
C23—H23A | 1.00 | C91—C92 | 1.391 (6) |
O31—C31 | 1.261 (5) | C91—C96 | 1.395 (6) |
O32—C31 | 1.250 (5) | C91—C97 | 1.507 (6) |
O33—C34 | 1.257 (5) | C92—C93 | 1.379 (7) |
O34—C34 | 1.242 (5) | C92—H92 | 0.95 |
O35—C32 | 1.429 (4) | C93—C94 | 1.381 (7) |
O35—H35 | 0.84 | C93—H93 | 0.95 |
O36—C33 | 1.429 (5) | C94—C95 | 1.379 (7) |
O36—H36 | 0.84 | C94—H94 | 0.95 |
C31—C32 | 1.543 (5) | C95—C96 | 1.383 (6) |
C32—C33 | 1.521 (5) | C95—H95 | 0.95 |
C32—H32A | 1.00 | C96—H96 | 0.95 |
C33—C34 | 1.542 (5) | C97—C98 | 1.522 (5) |
C33—H33A | 1.00 | C97—H97 | 1.00 |
O41—C41 | 1.267 (5) | C98—H98A | 0.98 |
O42—C41 | 1.257 (5) | C98—H98B | 0.98 |
O43—C44 | 1.253 (5) | C98—H98C | 0.98 |
O44—C44 | 1.231 (5) | N10—C107 | 1.496 (5) |
O45—C42 | 1.417 (4) | N10—H10A | 0.91 |
O45—H45 | 0.84 | N10—H10B | 0.91 |
O46—C43 | 1.426 (5) | N10—H10C | 0.91 |
O46—H46 | 0.84 | C101—C106 | 1.380 (6) |
C41—C42 | 1.542 (5) | C101—C102 | 1.388 (6) |
C42—C43 | 1.515 (5) | C101—C107 | 1.524 (5) |
C42—H42A | 1.00 | C102—C103 | 1.396 (7) |
C43—C44 | 1.533 (5) | C102—H102 | 0.95 |
C43—H43A | 1.00 | C103—C104 | 1.377 (7) |
N5—C57 | 1.513 (5) | C103—H103 | 0.95 |
N5—H5A | 0.91 | C104—C105 | 1.378 (8) |
N5—H5B | 0.91 | C104—H104 | 0.95 |
N5—H5C | 0.91 | C105—C106 | 1.391 (6) |
C51—C56 | 1.393 (6) | C105—H105 | 0.95 |
C51—C52 | 1.395 (6) | C106—H106 | 0.95 |
C51—C57 | 1.514 (6) | C107—C108 | 1.523 (5) |
C52—C53 | 1.385 (6) | C107—H107 | 1.00 |
C52—H52 | 0.95 | C108—H10D | 0.98 |
C53—C54 | 1.375 (8) | C108—H10E | 0.98 |
C53—H53 | 0.95 | C108—H10F | 0.98 |
C54—C55 | 1.370 (8) | N11—C117 | 1.512 (5) |
C54—H54 | 0.95 | N11—H11A | 0.91 |
C55—C56 | 1.401 (7) | N11—H11B | 0.91 |
C55—H55 | 0.95 | N11—H11C | 0.91 |
C56—H56 | 0.95 | C111—C112 | 1.394 (6) |
C57—C58 | 1.516 (6) | C111—C116 | 1.395 (6) |
C57—H57 | 1.00 | C111—C117 | 1.508 (6) |
C58—H58A | 0.98 | C112—C113 | 1.379 (6) |
C58—H58B | 0.98 | C112—H112 | 0.95 |
C58—H58C | 0.98 | C113—C114 | 1.376 (7) |
N6—C67 | 1.501 (5) | C113—H113 | 0.95 |
N6—H6A | 0.91 | C114—C115 | 1.387 (7) |
N6—H6B | 0.91 | C114—H114 | 0.95 |
N6—H6C | 0.91 | C115—C116 | 1.380 (6) |
C61—C62 | 1.385 (6) | C115—H115 | 0.95 |
C61—C66 | 1.404 (6) | C116—H116 | 0.95 |
C61—C67 | 1.505 (5) | C117—C118 | 1.463 (6) |
C62—C63 | 1.393 (6) | C117—H117 | 1.00 |
C62—H62 | 0.95 | C118—H11D | 0.98 |
C63—C64 | 1.385 (6) | C118—H11E | 0.98 |
C63—H63 | 0.95 | C118—H11F | 0.98 |
C64—C65 | 1.384 (7) | N12—C127 | 1.506 (5) |
C64—H64 | 0.95 | N12—H12A | 0.91 |
C65—C66 | 1.393 (6) | N12—H12B | 0.91 |
C65—H65 | 0.95 | N12—H12C | 0.91 |
C66—H66 | 0.95 | C121—C122 | 1.391 (6) |
C67—C68 | 1.504 (6) | C121—C126 | 1.402 (6) |
C67—H67 | 1.00 | C121—C127 | 1.511 (6) |
C68—H68A | 0.98 | C122—C123 | 1.392 (7) |
C68—H68B | 0.98 | C122—H122 | 0.95 |
C68—H68C | 0.98 | C123—C124 | 1.368 (8) |
N7—C77 | 1.503 (5) | C123—H123 | 0.95 |
N7—H7A | 0.91 | C124—C125 | 1.381 (8) |
N7—H7B | 0.91 | C124—H124 | 0.95 |
N7—H7C | 0.91 | C125—C126 | 1.381 (7) |
C71—C72 | 1.393 (5) | C125—H125 | 0.95 |
C71—C76 | 1.399 (6) | C126—H126 | 0.95 |
C71—C77 | 1.511 (6) | C127—C128 | 1.516 (5) |
C72—C73 | 1.378 (6) | C127—H127 | 1.00 |
C72—H72 | 0.95 | C128—H12E | 0.98 |
C73—C74 | 1.380 (6) | C128—H12F | 0.98 |
C73—H73 | 0.95 | C128—H12G | 0.98 |
C74—C75 | 1.378 (6) | O1—C1 | 1.304 (8) |
C74—H74 | 0.95 | O1—H1 | 0.84 |
C75—C76 | 1.386 (6) | C1—H1A | 0.98 |
C75—H75 | 0.95 | C1—H1B | 0.98 |
C76—H76 | 0.95 | C1—H1C | 0.98 |
C77—C78 | 1.509 (6) | O2—C2 | 1.380 (11) |
C77—H77 | 1.00 | O2—H2 | 0.84 |
C78—H78A | 0.98 | C2—H2A | 0.98 |
C78—H78B | 0.98 | C2—H2B | 0.98 |
C78—H78C | 0.98 | C2—H2C | 0.98 |
C12—O15—H15 | 109.5 | C87—N8—H8C | 109.5 |
C13—O16—H16 | 109.5 | H8A—N8—H8C | 109.5 |
O12—C11—O11 | 124.2 (3) | H8B—N8—H8C | 109.5 |
O12—C11—C12 | 118.4 (3) | C86—C81—C82 | 119.0 (4) |
O11—C11—C12 | 117.4 (3) | C86—C81—C87 | 118.8 (3) |
O15—C12—C13 | 111.3 (3) | C82—C81—C87 | 122.1 (4) |
O15—C12—C11 | 111.2 (3) | C83—C82—C81 | 120.1 (4) |
C13—C12—C11 | 111.2 (3) | C83—C82—H82 | 119.9 |
O15—C12—H12D | 107.6 | C81—C82—H82 | 119.9 |
C13—C12—H12D | 107.6 | C82—C83—C84 | 120.0 (4) |
C11—C12—H12D | 107.6 | C82—C83—H83 | 120.0 |
O16—C13—C12 | 107.7 (3) | C84—C83—H83 | 120.0 |
O16—C13—C14 | 112.4 (3) | C85—C84—C83 | 119.9 (5) |
C12—C13—C14 | 111.4 (3) | C85—C84—H84 | 120.0 |
O16—C13—H13A | 108.4 | C83—C84—H84 | 120.0 |
C12—C13—H13A | 108.4 | C84—C85—C86 | 120.2 (5) |
C14—C13—H13A | 108.4 | C84—C85—H85 | 119.9 |
O14—C14—O13 | 125.6 (4) | C86—C85—H85 | 119.9 |
O14—C14—C13 | 117.6 (3) | C85—C86—C81 | 120.7 (4) |
O13—C14—C13 | 116.8 (4) | C85—C86—H86 | 119.6 |
C22—O25—H25 | 109.5 | C81—C86—H86 | 119.6 |
C23—O26—H26 | 109.5 | N8—C87—C81 | 112.1 (3) |
O21—C21—O22 | 124.7 (3) | N8—C87—C88 | 109.2 (3) |
O21—C21—C22 | 117.3 (3) | C81—C87—C88 | 112.0 (3) |
O22—C21—C22 | 117.9 (3) | N8—C87—H87 | 107.8 |
O25—C22—C23 | 111.6 (3) | C81—C87—H87 | 107.8 |
O25—C22—C21 | 112.1 (3) | C88—C87—H87 | 107.8 |
C23—C22—C21 | 110.6 (3) | C87—C88—H88A | 109.5 |
O25—C22—H22A | 107.5 | C87—C88—H88B | 109.5 |
C23—C22—H22A | 107.5 | H88A—C88—H88B | 109.5 |
C21—C22—H22A | 107.5 | C87—C88—H88C | 109.5 |
O26—C23—C22 | 108.3 (3) | H88A—C88—H88C | 109.5 |
O26—C23—C24 | 112.3 (3) | H88B—C88—H88C | 109.5 |
C22—C23—C24 | 111.3 (3) | C97—N9—H9A | 109.5 |
O26—C23—H23A | 108.3 | C97—N9—H9B | 109.5 |
C22—C23—H23A | 108.3 | H9A—N9—H9B | 109.5 |
C24—C23—H23A | 108.3 | C97—N9—H9C | 109.5 |
O24—C24—O23 | 124.8 (4) | H9A—N9—H9C | 109.5 |
O24—C24—C23 | 117.5 (3) | H9B—N9—H9C | 109.5 |
O23—C24—C23 | 117.6 (3) | C92—C91—C96 | 117.6 (4) |
C32—O35—H35 | 109.5 | C92—C91—C97 | 123.2 (4) |
C33—O36—H36 | 109.5 | C96—C91—C97 | 119.0 (3) |
O32—C31—O31 | 125.0 (3) | C93—C92—C91 | 121.3 (4) |
O32—C31—C32 | 118.4 (3) | C93—C92—H92 | 119.3 |
O31—C31—C32 | 116.6 (3) | C91—C92—H92 | 119.3 |
O35—C32—C33 | 111.2 (3) | C92—C93—C94 | 120.1 (5) |
O35—C32—C31 | 110.9 (3) | C92—C93—H93 | 120.0 |
C33—C32—C31 | 111.3 (3) | C94—C93—H93 | 120.0 |
O35—C32—H32A | 107.7 | C95—C94—C93 | 119.7 (4) |
C33—C32—H32A | 107.7 | C95—C94—H94 | 120.2 |
C31—C32—H32A | 107.7 | C93—C94—H94 | 120.2 |
O36—C33—C32 | 107.9 (3) | C94—C95—C96 | 120.1 (4) |
O36—C33—C34 | 111.8 (3) | C94—C95—H95 | 120.0 |
C32—C33—C34 | 110.9 (3) | C96—C95—H95 | 120.0 |
O36—C33—H33A | 108.7 | C95—C96—C91 | 121.1 (4) |
C32—C33—H33A | 108.7 | C95—C96—H96 | 119.5 |
C34—C33—H33A | 108.7 | C91—C96—H96 | 119.5 |
O34—C34—O33 | 125.4 (4) | C91—C97—N9 | 111.4 (3) |
O34—C34—C33 | 118.0 (4) | C91—C97—C98 | 111.2 (3) |
O33—C34—C33 | 116.6 (3) | N9—C97—C98 | 108.5 (3) |
C42—O45—H45 | 109.5 | C91—C97—H97 | 108.6 |
C43—O46—H46 | 109.5 | N9—C97—H97 | 108.6 |
O42—C41—O41 | 124.3 (3) | C98—C97—H97 | 108.6 |
O42—C41—C42 | 118.3 (3) | C97—C98—H98A | 109.5 |
O41—C41—C42 | 117.3 (3) | C97—C98—H98B | 109.5 |
O45—C42—C43 | 112.0 (3) | H98A—C98—H98B | 109.5 |
O45—C42—C41 | 111.9 (3) | C97—C98—H98C | 109.5 |
C43—C42—C41 | 110.9 (3) | H98A—C98—H98C | 109.5 |
O45—C42—H42A | 107.3 | H98B—C98—H98C | 109.5 |
C43—C42—H42A | 107.3 | C107—N10—H10A | 109.5 |
C41—C42—H42A | 107.3 | C107—N10—H10B | 109.5 |
O46—C43—C42 | 107.9 (3) | H10A—N10—H10B | 109.5 |
O46—C43—C44 | 112.9 (3) | C107—N10—H10C | 109.5 |
C42—C43—C44 | 111.5 (3) | H10A—N10—H10C | 109.5 |
O46—C43—H43A | 108.1 | H10B—N10—H10C | 109.5 |
C42—C43—H43A | 108.1 | C106—C101—C102 | 119.4 (4) |
C44—C43—H43A | 108.1 | C106—C101—C107 | 118.8 (4) |
O44—C44—O43 | 124.1 (4) | C102—C101—C107 | 121.6 (4) |
O44—C44—C43 | 117.8 (4) | C101—C102—C103 | 119.7 (4) |
O43—C44—C43 | 118.2 (3) | C101—C102—H102 | 120.1 |
C57—N5—H5A | 109.5 | C103—C102—H102 | 120.1 |
C57—N5—H5B | 109.5 | C104—C103—C102 | 120.6 (5) |
H5A—N5—H5B | 109.5 | C104—C103—H103 | 119.7 |
C57—N5—H5C | 109.5 | C102—C103—H103 | 119.7 |
H5A—N5—H5C | 109.5 | C103—C104—C105 | 119.5 (4) |
H5B—N5—H5C | 109.5 | C103—C104—H104 | 120.2 |
C56—C51—C52 | 118.2 (4) | C105—C104—H104 | 120.2 |
C56—C51—C57 | 119.4 (4) | C104—C105—C106 | 120.2 (4) |
C52—C51—C57 | 122.4 (4) | C104—C105—H105 | 119.9 |
C53—C52—C51 | 121.3 (4) | C106—C105—H105 | 119.9 |
C53—C52—H52 | 119.3 | C101—C106—C105 | 120.5 (4) |
C51—C52—H52 | 119.3 | C101—C106—H106 | 119.7 |
C54—C53—C52 | 119.6 (5) | C105—C106—H106 | 119.7 |
C54—C53—H53 | 120.2 | N10—C107—C108 | 110.1 (3) |
C52—C53—H53 | 120.2 | N10—C107—C101 | 111.3 (3) |
C55—C54—C53 | 120.5 (4) | C108—C107—C101 | 111.8 (3) |
C55—C54—H54 | 119.8 | N10—C107—H107 | 107.9 |
C53—C54—H54 | 119.8 | C108—C107—H107 | 107.9 |
C54—C55—C56 | 120.3 (5) | C101—C107—H107 | 107.9 |
C54—C55—H55 | 119.8 | C107—C108—H10D | 109.5 |
C56—C55—H55 | 119.8 | C107—C108—H10E | 109.5 |
C51—C56—C55 | 120.1 (5) | H10D—C108—H10E | 109.5 |
C51—C56—H56 | 120.0 | C107—C108—H10F | 109.5 |
C55—C56—H56 | 120.0 | H10D—C108—H10F | 109.5 |
N5—C57—C51 | 111.5 (3) | H10E—C108—H10F | 109.5 |
N5—C57—C58 | 108.3 (3) | C117—N11—H11A | 109.5 |
C51—C57—C58 | 113.9 (3) | C117—N11—H11B | 109.5 |
N5—C57—H57 | 107.6 | H11A—N11—H11B | 109.5 |
C51—C57—H57 | 107.6 | C117—N11—H11C | 109.5 |
C58—C57—H57 | 107.6 | H11A—N11—H11C | 109.5 |
C57—C58—H58A | 109.5 | H11B—N11—H11C | 109.5 |
C57—C58—H58B | 109.5 | C112—C111—C116 | 118.4 (4) |
H58A—C58—H58B | 109.5 | C112—C111—C117 | 122.9 (4) |
C57—C58—H58C | 109.5 | C116—C111—C117 | 118.7 (4) |
H58A—C58—H58C | 109.5 | C113—C112—C111 | 121.1 (4) |
H58B—C58—H58C | 109.5 | C113—C112—H112 | 119.5 |
C67—N6—H6A | 109.5 | C111—C112—H112 | 119.5 |
C67—N6—H6B | 109.5 | C114—C113—C112 | 120.2 (4) |
H6A—N6—H6B | 109.5 | C114—C113—H113 | 119.9 |
C67—N6—H6C | 109.5 | C112—C113—H113 | 119.9 |
H6A—N6—H6C | 109.5 | C113—C114—C115 | 119.4 (4) |
H6B—N6—H6C | 109.5 | C113—C114—H114 | 120.3 |
C62—C61—C66 | 118.8 (4) | C115—C114—H114 | 120.3 |
C62—C61—C67 | 121.9 (4) | C116—C115—C114 | 120.8 (4) |
C66—C61—C67 | 119.3 (4) | C116—C115—H115 | 119.6 |
C61—C62—C63 | 121.1 (4) | C114—C115—H115 | 119.6 |
C61—C62—H62 | 119.4 | C115—C116—C111 | 120.1 (4) |
C63—C62—H62 | 119.4 | C115—C116—H116 | 119.9 |
C64—C63—C62 | 119.5 (4) | C111—C116—H116 | 119.9 |
C64—C63—H63 | 120.3 | C118—C117—C111 | 114.2 (4) |
C62—C63—H63 | 120.3 | C118—C117—N11 | 110.0 (4) |
C65—C64—C63 | 120.4 (4) | C111—C117—N11 | 109.5 (3) |
C65—C64—H64 | 119.8 | C118—C117—H117 | 107.6 |
C63—C64—H64 | 119.8 | C111—C117—H117 | 107.6 |
C64—C65—C66 | 120.0 (4) | N11—C117—H117 | 107.6 |
C64—C65—H65 | 120.0 | C117—C118—H11D | 109.5 |
C66—C65—H65 | 120.0 | C117—C118—H11E | 109.5 |
C65—C66—C61 | 120.2 (4) | H11D—C118—H11E | 109.5 |
C65—C66—H66 | 119.9 | C117—C118—H11F | 109.5 |
C61—C66—H66 | 119.9 | H11D—C118—H11F | 109.5 |
N6—C67—C68 | 109.2 (3) | H11E—C118—H11F | 109.5 |
N6—C67—C61 | 110.4 (3) | C127—N12—H12A | 109.5 |
C68—C67—C61 | 113.9 (4) | C127—N12—H12B | 109.5 |
N6—C67—H67 | 107.7 | H12A—N12—H12B | 109.5 |
C68—C67—H67 | 107.7 | C127—N12—H12C | 109.5 |
C61—C67—H67 | 107.7 | H12A—N12—H12C | 109.5 |
C67—C68—H68A | 109.5 | H12B—N12—H12C | 109.5 |
C67—C68—H68B | 109.5 | C122—C121—C126 | 118.5 (4) |
H68A—C68—H68B | 109.5 | C122—C121—C127 | 122.1 (4) |
C67—C68—H68C | 109.5 | C126—C121—C127 | 119.2 (4) |
H68A—C68—H68C | 109.5 | C121—C122—C123 | 120.6 (5) |
H68B—C68—H68C | 109.5 | C121—C122—H122 | 119.7 |
C77—N7—H7A | 109.5 | C123—C122—H122 | 119.7 |
C77—N7—H7B | 109.5 | C124—C123—C122 | 119.9 (5) |
H7A—N7—H7B | 109.5 | C124—C123—H123 | 120.0 |
C77—N7—H7C | 109.5 | C122—C123—H123 | 120.0 |
H7A—N7—H7C | 109.5 | C123—C124—C125 | 120.4 (5) |
H7B—N7—H7C | 109.5 | C123—C124—H124 | 119.8 |
C72—C71—C76 | 118.2 (4) | C125—C124—H124 | 119.8 |
C72—C71—C77 | 122.8 (4) | C126—C125—C124 | 120.2 (5) |
C76—C71—C77 | 119.0 (3) | C126—C125—H125 | 119.9 |
C73—C72—C71 | 120.6 (4) | C124—C125—H125 | 119.9 |
C73—C72—H72 | 119.7 | C125—C126—C121 | 120.3 (5) |
C71—C72—H72 | 119.7 | C125—C126—H126 | 119.9 |
C72—C73—C74 | 120.8 (4) | C121—C126—H126 | 119.9 |
C72—C73—H73 | 119.6 | N12—C127—C121 | 112.2 (3) |
C74—C73—H73 | 119.6 | N12—C127—C128 | 107.9 (3) |
C75—C74—C73 | 119.5 (4) | C121—C127—C128 | 112.5 (3) |
C75—C74—H74 | 120.3 | N12—C127—H127 | 108.0 |
C73—C74—H74 | 120.3 | C121—C127—H127 | 108.0 |
C74—C75—C76 | 120.3 (4) | C128—C127—H127 | 108.0 |
C74—C75—H75 | 119.9 | C127—C128—H12E | 109.5 |
C76—C75—H75 | 119.9 | C127—C128—H12F | 109.5 |
C75—C76—C71 | 120.6 (4) | H12E—C128—H12F | 109.5 |
C75—C76—H76 | 119.7 | C127—C128—H12G | 109.5 |
C71—C76—H76 | 119.7 | H12E—C128—H12G | 109.5 |
N7—C77—C78 | 108.8 (3) | H12F—C128—H12G | 109.5 |
N7—C77—C71 | 111.3 (3) | C1—O1—H1 | 109.5 |
C78—C77—C71 | 113.9 (3) | O1—C1—H1A | 109.5 |
N7—C77—H77 | 107.5 | O1—C1—H1B | 109.5 |
C78—C77—H77 | 107.5 | H1A—C1—H1B | 109.5 |
C71—C77—H77 | 107.5 | O1—C1—H1C | 109.5 |
C77—C78—H78A | 109.5 | H1A—C1—H1C | 109.5 |
C77—C78—H78B | 109.5 | H1B—C1—H1C | 109.5 |
H78A—C78—H78B | 109.5 | C2—O2—H2 | 109.5 |
C77—C78—H78C | 109.5 | O2—C2—H2A | 109.5 |
H78A—C78—H78C | 109.5 | O2—C2—H2B | 109.5 |
H78B—C78—H78C | 109.5 | H2A—C2—H2B | 109.5 |
C87—N8—H8A | 109.5 | O2—C2—H2C | 109.5 |
C87—N8—H8B | 109.5 | H2A—C2—H2C | 109.5 |
H8A—N8—H8B | 109.5 | H2B—C2—H2C | 109.5 |
D—H···A | D—H | H···A | D···A | D—H···A |
O15—H15···O12 | 0.84 | 2.37 | 2.661 (4) | 101 |
O15—H15···O34i | 0.84 | 1.84 | 2.628 (4) | 156 |
O16—H16···O21 | 0.84 | 1.90 | 2.722 (4) | 167 |
O25—H25···O22 | 0.84 | 2.38 | 2.675 (4) | 101 |
O25—H25···O44ii | 0.84 | 1.82 | 2.584 (4) | 150 |
O26—H26···O11 | 0.84 | 1.89 | 2.712 (4) | 168 |
O35—H35···O14 | 0.84 | 1.83 | 2.617 (4) | 156 |
O36—H36···O41 | 0.84 | 1.91 | 2.741 (4) | 171 |
O45—H45···O42 | 0.84 | 2.38 | 2.677 (4) | 101 |
O45—H45···O24iii | 0.84 | 1.82 | 2.585 (4) | 150 |
O46—H46···O31 | 0.84 | 1.88 | 2.711 (4) | 171 |
N5—H5A···O23iii | 0.91 | 1.98 | 2.885 (4) | 171 |
N5—H5B···O22iv | 0.91 | 1.99 | 2.882 (4) | 168 |
N5—H5C···O46 | 0.91 | 2.00 | 2.902 (4) | 173 |
N6—H6A···O45 | 0.91 | 2.10 | 2.973 (4) | 161 |
N6—H6B···O22iv | 0.91 | 1.96 | 2.858 (4) | 169 |
N6—H6C···O11iii | 0.91 | 1.89 | 2.768 (4) | 160 |
N7—H7A···O43v | 0.91 | 2.01 | 2.898 (4) | 167 |
N7—H7B···O42 | 0.91 | 1.95 | 2.859 (4) | 173 |
N7—H7C···O26iii | 0.91 | 2.00 | 2.906 (4) | 178 |
N8—H8A···O33i | 0.91 | 1.93 | 2.822 (4) | 168 |
N8—H8B···O16 | 0.91 | 2.03 | 2.912 (4) | 163 |
N8—H8C···O32 | 0.91 | 1.96 | 2.869 (4) | 175 |
N9—H9A···O41i | 0.91 | 1.93 | 2.832 (4) | 169 |
N9—H9B···O32 | 0.91 | 2.00 | 2.891 (4) | 167 |
N9—H9C···O15 | 0.91 | 1.92 | 2.825 (4) | 174 |
N10—H10A···O36 | 0.91 | 2.04 | 2.920 (4) | 162 |
N10—H10B···O12v | 0.91 | 1.95 | 2.852 (4) | 173 |
N10—H10C···O13 | 0.91 | 1.93 | 2.819 (4) | 165 |
N11—H11A···O42vi | 0.91 | 1.96 | 2.863 (4) | 171 |
N11—H11B···O31ii | 0.91 | 1.91 | 2.781 (4) | 160 |
N11—H11C···O25 | 0.91 | 2.03 | 2.918 (4) | 163 |
N12—H12A···O21 | 0.91 | 1.93 | 2.832 (4) | 170 |
N12—H12B···O12v | 0.91 | 2.00 | 2.906 (4) | 172 |
N12—H12C···O35 | 0.91 | 1.94 | 2.844 (4) | 177 |
O1—H1···O23 | 0.84 | 1.90 | 2.730 (5) | 170 |
O2—H2···O43 | 0.84 | 1.97 | 2.791 (5) | 164 |
Symmetry codes: (i) x−1, y, z; (ii) x, y−1, z; (iii) x+1, y+1, z; (iv) x, y+1, z; (v) x+1, y, z; (vi) x−1, y−1, z. |
Experimental details
(I) | (II) | (III) | (IV) | |
Crystal data | ||||
Chemical formula | C8H12N·C4H5O6 | C8H12N·C4H5O6 | C8H12N·C4H5O6 | 2(C8H12N)·C4H4O6 |
Mr | 271.27 | 271.27 | 271.27 | 392.44 |
Crystal system, space group | Monoclinic, P21 | Monoclinic, P21 | Monoclinic, P21 | Monoclinic, P21 |
Temperature (K) | 150 | 150 | 150 | 150 |
a, b, c (Å) | 6.3425 (2), 13.9448 (3), 7.5021 (3) | 7.3025 (2), 22.8901 (11), 8.1193 (3) | 7.2952 (2), 22.8935 (11), 8.1100 (3) | 5.5620 (2), 16.0630 (3), 11.8260 (4) |
α, β, γ (°) | 90, 107.6599 (14), 90 | 90, 96.599 (2), 90 | 90, 96.603 (2), 90 | 90, 103.2810 (12), 90 |
V (Å3) | 632.25 (4) | 1348.19 (9) | 1345.49 (9) | 1028.31 (5) |
Z | 2 | 4 | 4 | 2 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.12 | 0.11 | 0.11 | 0.09 |
Crystal size (mm) | 0.30 × 0.25 × 0.22 | 0.28 × 0.16 × 0.14 | 0.36 × 0.26 × 0.20 | 0.36 × 0.26 × 0.10 |
Data collection | ||||
Diffractometer | Kappa-CCD diffractometer | Kappa-CCD diffractometer | Kappa-CCD diffractometer | Kappa-CCD diffractometer |
Absorption correction | Multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | Multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | Multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | Multi-scan DENZO-SMN (Otwinowski & Minor, 1997) |
Tmin, Tmax | 0.923, 0.983 | 0.584, 0.998 | 0.869, 0.991 | 0.877, 0.995 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5067, 1497, 1386 | 15852, 3191, 2734 | 9403, 3160, 2446 | 8194, 2434, 2187 |
Rint | 0.042 | 0.129 | 0.061 | 0.050 |
(sin θ/λ)max (Å−1) | 0.649 | 0.653 | 0.650 | 0.649 |
Refinement | ||||
R[F2 > 2σ(F2)], wR(F2), S | 0.032, 0.077, 1.09 | 0.047, 0.130, 1.06 | 0.040, 0.091, 1.04 | 0.035, 0.094, 1.05 |
No. of reflections | 1497 | 3191 | 3160 | 2434 |
No. of parameters | 177 | 354 | 354 | 260 |
No. of restraints | 1 | 1 | 1 | 1 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.16, −0.20 | 0.34, −0.24 | 0.18, −0.21 | 0.22, −0.24 |
(V) | (VI) | |
Crystal data | ||
Chemical formula | 2(C8H12N)·C4H4O6 | 4(C8H12N)·2(C4H4O6)·CH4O |
Mr | 392.44 | 816.93 |
Crystal system, space group | Monoclinic, P21 | Triclinic, P1 |
Temperature (K) | 150 | 150 |
a, b, c (Å) | 8.3381 (14), 22.738 (4), 10.8190 (18) | 9.0822 (3), 15.7819 (5), 15.9040 (5) |
α, β, γ (°) | 90, 90.120 (3), 90 | 108.7460 (15), 96.858 (2), 90.0600 (18) |
V (Å3) | 2051.2 (6) | 2141.33 (12) |
Z | 4 | 2 |
Radiation type | Synchrotron, λ = 0.6900 Å | Mo Kα |
µ (mm−1) | 0.09 | 0.09 |
Crystal size (mm) | 0.30 × 0.22 × 0.06 | 0.20 × 0.16 × 0.08 |
Data collection | ||
Diffractometer | Kappa-CCD diffractometer | Kappa-CCD diffractometer |
Absorption correction | Multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | Multi-scan DENZO-SMN (Otwinowski & Minor, 1997) |
Tmin, Tmax | 0.972, 0.994 | 0.975, 0.993 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 18641, 5818, 5504 | 28530, 9771, 6899 |
Rint | 0.034 | 0.094 |
(sin θ/λ)max (Å−1) | 0.711 | 0.651 |
Refinement | ||
R[F2 > 2σ(F2)], wR(F2), S | 0.054, 0.151, 1.16 | 0.051, 0.132, 1.04 |
No. of reflections | 5818 | 9771 |
No. of parameters | 517 | 1074 |
No. of restraints | 1 | 3 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.59, −0.34 | 0.44, −0.40 |
Computer programs: Kappa-CCD server software (Nonius, 1997), DENZO-SMN (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97 and PRPKAPPA (Ferguson, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O1i | 0.84 | 1.65 | 2.486 (2) | 174 |
O5—H5···O2 | 0.84 | 2.11 | 2.616 (2) | 119 |
O5—H5···O4ii | 0.84 | 2.18 | 2.797 (2) | 130 |
O6—H6···O3 | 0.84 | 2.17 | 2.652 (2) | 116 |
N1—H1A···O1 | 0.91 | 2.00 | 2.901 (2) | 172 |
N1—H1B···O5iii | 0.91 | 2.02 | 2.867 (2) | 154 |
N1—H1C···O2iv | 0.91 | 1.93 | 2.842 (2) | 177 |
Symmetry codes: (i) x, y, z−1; (ii) x−1, y, z; (iii) x+1, y, z+1; (iv) x+1, y, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O15—H15···O12 | 0.84 | 2.11 | 2.607 (3) | 118 |
O15—H15···O22i | 0.84 | 2.28 | 2.941 (3) | 136 |
O16—H16···O21 | 0.84 | 1.92 | 2.750 (3) | 169 |
O14—H14···O11ii | 0.84 | 1.73 | 2.571 (3) | 175 |
O25—H25···O22 | 0.84 | 2.11 | 2.610 (3) | 118 |
O25—H25···O12iii | 0.84 | 2.36 | 3.022 (3) | 136 |
O26—H26···O11 | 0.84 | 1.94 | 2.771 (3) | 170 |
O24—H24···O21iv | 0.84 | 1.74 | 2.576 (3) | 177 |
N3—H3A···O12 | 0.91 | 1.85 | 2.749 (3) | 167 |
N3—H3B···O15iv | 0.91 | 1.96 | 2.850 (3) | 164 |
N3—H3C···O26i | 0.91 | 2.11 | 2.945 (3) | 152 |
N3—H3C···O23i | 0.91 | 2.36 | 2.894 (3) | 118 |
N4—H4A···O22 | 0.91 | 1.87 | 2.753 (3) | 162 |
N4—H4B···O25ii | 0.91 | 1.93 | 2.828 (3) | 169 |
N4—H4C···O16iii | 0.91 | 2.15 | 2.956 (3) | 147 |
N4—H4C···O13iii | 0.91 | 2.27 | 2.919 (3) | 128 |
Symmetry codes: (i) x, y, z+1; (ii) x+1, y, z; (iii) x, y, z−1; (iv) x−1, y, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O15—H15···O12 | 0.84 | 2.13 | 2.605 (2) | 116 |
O15—H15···O22i | 0.84 | 2.22 | 2.944 (3) | 144 |
O16—H16···O21 | 0.84 | 1.92 | 2.750 (3) | 170 |
O14—H14···O11ii | 0.84 | 1.73 | 2.568 (2) | 176 |
O25—H25···O22 | 0.84 | 2.11 | 2.604 (2) | 117 |
O25—H25···O12iii | 0.84 | 2.35 | 3.019 (3) | 136 |
O26—H26···O11 | 0.84 | 1.94 | 2.773 (3) | 169 |
O24—H24···O21iv | 0.84 | 1.74 | 2.575 (2) | 177 |
N3—H3A···O26i | 0.91 | 2.11 | 2.945 (3) | 152 |
N3—H3A···O23i | 0.91 | 2.35 | 2.893 (3) | 118 |
N3—H3B···O15iv | 0.91 | 1.96 | 2.847 (3) | 165 |
N3—H3C···O12 | 0.91 | 1.85 | 2.747 (3) | 167 |
N4—H4A···O16iii | 0.91 | 2.15 | 2.956 (3) | 147 |
N4—H4A···O13iii | 0.91 | 2.25 | 2.916 (3) | 129 |
N4—H4B···O25ii | 0.91 | 1.93 | 2.824 (3) | 169 |
N4—H4C···O22 | 0.91 | 1.87 | 2.752 (3) | 162 |
C36—H36···Cgv | 0.95 | 2.87 | 3.775 (3) | 160 |
Symmetry codes: (i) x, y, z+1; (ii) x+1, y, z; (iii) x, y, z−1; (iv) x−1, y, z; (v) −x+1, y−1/2, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5···O1i | 0.84 | 2.07 | 2.882 (2) | 161 |
O5—H5···O6 | 0.84 | 2.46 | 2.860 (2) | 110 |
O6—H6···O3 | 0.84 | 2.11 | 2.603 (2) | 117 |
N1—H1A···O2ii | 0.91 | 1.88 | 2.759 (2) | 161 |
N1—H1B···O4 | 0.91 | 1.93 | 2.823 (2) | 167 |
N1—H1C···O1iii | 0.91 | 1.89 | 2.745 (2) | 155 |
N2—H2A···O4 | 0.91 | 1.84 | 2.746 (2) | 172 |
N2—H2B···O2iii | 0.91 | 1.91 | 2.774 (2) | 158 |
N2—H2C···O3iv | 0.91 | 1.85 | 2.720 (2) | 159 |
Symmetry codes: (i) x+1, y, z; (ii) −x+1, y−1/2, −z+1; (iii) −x, y−1/2, −z+1; (iv) x−1, y, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O15—H15···O22i | 0.84 | 1.91 | 2.743 (3) | 169 |
O16—H16···O23ii | 0.84 | 1.87 | 2.690 (3) | 164 |
O25—H25···O11 | 0.84 | 1.86 | 2.681 (3) | 167 |
O26—H26···O13iii | 0.84 | 1.91 | 2.743 (3) | 169 |
N3—H3A···O12 | 0.91 | 1.90 | 2.801 (3) | 171 |
N3—H3B···O22 | 0.91 | 1.82 | 2.718 (4) | 168 |
N3—H3C···O14iv | 0.91 | 1.89 | 2.777 (3) | 165 |
N4—H4A···O23v | 0.91 | 1.85 | 2.738 (3) | 165 |
N4—H4B···O12i | 0.91 | 1.92 | 2.825 (3) | 170 |
N4—H4C···O14 | 0.91 | 1.98 | 2.798 (3) | 149 |
N5—H5A···O21v | 0.91 | 1.89 | 2.774 (3) | 164 |
N5—H5B···O24ii | 0.91 | 1.89 | 2.798 (3) | 173 |
N5—H5C···O13 | 0.91 | 1.83 | 2.716 (3) | 164 |
N6—H6A···O24 | 0.91 | 1.95 | 2.847 (3) | 171 |
N6—H6B···O21i | 0.91 | 1.96 | 2.803 (3) | 154 |
N6—H6C···O11 | 0.91 | 1.86 | 2.747 (3) | 164 |
Symmetry codes: (i) x+1, y, z; (ii) x, y, z+1; (iii) x−1, y, z−1; (iv) x−1, y, z; (v) x+1, y, z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O15—H15···O12 | 0.84 | 2.37 | 2.661 (4) | 101 |
O15—H15···O34i | 0.84 | 1.84 | 2.628 (4) | 156 |
O16—H16···O21 | 0.84 | 1.90 | 2.722 (4) | 167 |
O25—H25···O22 | 0.84 | 2.38 | 2.675 (4) | 101 |
O25—H25···O44ii | 0.84 | 1.82 | 2.584 (4) | 150 |
O26—H26···O11 | 0.84 | 1.89 | 2.712 (4) | 168 |
O35—H35···O14 | 0.84 | 1.83 | 2.617 (4) | 156 |
O36—H36···O41 | 0.84 | 1.91 | 2.741 (4) | 171 |
O45—H45···O42 | 0.84 | 2.38 | 2.677 (4) | 101 |
O45—H45···O24iii | 0.84 | 1.82 | 2.585 (4) | 150 |
O46—H46···O31 | 0.84 | 1.88 | 2.711 (4) | 171 |
N5—H5A···O23iii | 0.91 | 1.98 | 2.885 (4) | 171 |
N5—H5B···O22iv | 0.91 | 1.99 | 2.882 (4) | 168 |
N5—H5C···O46 | 0.91 | 2.00 | 2.902 (4) | 173 |
N6—H6A···O45 | 0.91 | 2.10 | 2.973 (4) | 161 |
N6—H6B···O22iv | 0.91 | 1.96 | 2.858 (4) | 169 |
N6—H6C···O11iii | 0.91 | 1.89 | 2.768 (4) | 160 |
N7—H7A···O43v | 0.91 | 2.01 | 2.898 (4) | 167 |
N7—H7B···O42 | 0.91 | 1.95 | 2.859 (4) | 173 |
N7—H7C···O26iii | 0.91 | 2.00 | 2.906 (4) | 178 |
N8—H8A···O33i | 0.91 | 1.93 | 2.822 (4) | 168 |
N8—H8B···O16 | 0.91 | 2.03 | 2.912 (4) | 163 |
N8—H8C···O32 | 0.91 | 1.96 | 2.869 (4) | 175 |
N9—H9A···O41i | 0.91 | 1.93 | 2.832 (4) | 169 |
N9—H9B···O32 | 0.91 | 2.00 | 2.891 (4) | 167 |
N9—H9C···O15 | 0.91 | 1.92 | 2.825 (4) | 174 |
N10—H10A···O36 | 0.91 | 2.04 | 2.920 (4) | 162 |
N10—H10B···O12v | 0.91 | 1.95 | 2.852 (4) | 173 |
N10—H10C···O13 | 0.91 | 1.93 | 2.819 (4) | 165 |
N11—H11A···O42vi | 0.91 | 1.96 | 2.863 (4) | 171 |
N11—H11B···O31ii | 0.91 | 1.91 | 2.781 (4) | 160 |
N11—H11C···O25 | 0.91 | 2.03 | 2.918 (4) | 163 |
N12—H12A···O21 | 0.91 | 1.93 | 2.832 (4) | 170 |
N12—H12B···O12v | 0.91 | 2.00 | 2.906 (4) | 172 |
N12—H12C···O35 | 0.91 | 1.94 | 2.844 (4) | 177 |
O1—H1···O23 | 0.84 | 1.90 | 2.730 (5) | 170 |
O2—H2···O43 | 0.84 | 1.97 | 2.791 (5) | 164 |
Symmetry codes: (i) x−1, y, z; (ii) x, y−1, z; (iii) x+1, y+1, z; (iv) x, y+1, z; (v) x+1, y, z; (vi) x−1, y−1, z. |
Acknowledgements
X-ray data were collected at the University of Toronto using a Nonius Kappa-CCD diffractometer purchased with funds from NSERC Canada. We acknowledge the CCLRC for provision of beamtime on Station 9.8 of the SRS.
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