research papers
Isostructural behaviour in ammonium and potassium salt forms of sulfonated azo dyes
aDepartment of Pure & Applied Chemistry, University of Strathclyde, Glasgow, G1 1XQ, United Kingdom
*Correspondence e-mail: a.r.kennedy@strath.ac.uk
The structures of five ammonium salt forms of monosulfonated azo dyes, derivatives of 4-(2-phenyldiazen-1-yl)benzenesulfonate, with the general formula [NH4][O3S(C6H4)NN(C6H3)RR′]·XH2O [R = OH, NH2 or N(C2H4OH)2; R′ = H or OH] are presented. All form simple layered structures with alternating hydrophobic (organic) and hydrophilic (cation, solvent and polar groups) layers. To assess for isostructural behaviour of the ammonium cation with M+ ions, the packing of these structures is compared with literature examples. To aid this comparison, the corresponding structures of four potassium salt forms of the monosulfonated azo dyes are also presented herein. Of the five ammonium salts it is found that three have isostructural equivalents. In two cases this equivalent is a potassium salt form and in one case it is a rubidium salt form. The isostructurality of ion packing and of unit-cell symmetry and dimensions tolerates cases where the ammonium ions form somewhat different interaction types with coformer species than do the potassium or rubidium ions. No sodium salt forms are found to be isostructural with any ammonium equivalent. However, similarities in the anion packing within a single hydrophobic layer are found for a group that consists of the ammonium and rubidium salt forms of one azo anion species and the sodium and silver salt forms of a different azo species.
1. Introduction
The process of salt selection aims to choose the form of an active organic material that has the best properties for effectiveness and for commercialization. Salt selection is well studied in the area of pharmaceuticals (Stahl & Wermuth, 2008; Mahmood et al., 2023; Bharate, 2021; Arlin et al., 2011; Black et al., 2007), but it is perhaps less well known that similar processes are used to select for material properties in other areas too. One example is the process of laking sulfonated azo colourants. A typical process here involves the substitution of an M+ cation with an M2+ cation, such as Ca or Ba, to switch from an aqueous-soluble dyestuff to an insoluble pigment (Christie & Mackay, 2008; Schmidt et al., 2009; Kennedy et al., 2012). As with pharmaceuticals, the material properties of pigments are dependant upon their crystal structures, and upon the intermolecular interactions present within the crystal (Hao & Iqbal, 1997). However, in the field of sulfonated azo colourants relatively few pigment structures are known due to the insoluble nature of the materials and to the highly anisotropic habits of many species. This means that a high percentage of the crystal structures that are known are derived from less common methods than standard single-crystal X-ray diffraction (e.g. structure from powder diffraction, from electron diffraction or through use of synchrotron radiation – see Schmidt et al., 2009; Gorelik et al., 2009; Kennedy et al., 2000; Grzesiak-Nowak et al., 2019). One strategy for understanding the structure of sulfonated azo pigments has been to study systematically the structures of similarly functionalized, but easier to manipulate, dyes and then to cross-check any structure-to-property relationships identified against those pigment structures that are known (Kennedy et al., 2004, 2009, 2012).
Ammonium salt forms of sulfonated azo colourants are sometimes used in preference to alkali-metal salts, either in the finished product or as an intermediate prior to laking (Christie & Mackay, 2008; Al Isawi et al., 2021; Gonzalez & Miksovska, 2014). Despite this, only two structures of ammonium salts of sulfonated azo colourants appear to have been determined, namely, those of diammonium Orange G tetrahydrate and of the nitrile-substituted [NH4][O3S(C6H4)NN(C6H4)NHCH2CH2CN]·H2O (Ojala et al., 1994; Astbury et al., 2013). The NH4+ ion is sometimes known as a pseudo-alkali metal due to it propensity to act in an isostructural manner with the heavier Group 1 metal ions. Its effective ionic radius has been estimated at 1.40 to 1.67 Å, depending on the (Sidey, 2016). Thus, as well as having the same charge as an alkali metal, it also has an ionic radius similar to those of K+ and Rb+. An obvious difference is that bonds from an alkali-metal ion to, for example, an O-atom donor are typically described as ionic M—O interactions, whereas NH4+ will interact with O via N—H⋯O hydrogen bonds. As there are four H-atom donors per ammonium ion this may limit NH4+ to lower coordination numbers than those typically seen for K or Rb. It seems to be this feature that is responsible for ammonium forming isostructural pairs with Na compounds, as well as with K and Rb compounds, despite the smaller ionic radius of Na+ (e.g. Khan & Baur, 1972; Christov, 2003; Emerson et al., 2014). Many examples of isostructurality between ammonium and Group 1 metal ions are for inorganic systems, but organic examples are also known. Of particular relevance to sulfonated azo species is the sweetener cyclamic acid. This is an RSO3−-containing organic species and its ammonium, Na, K and Rb salt forms are known to form an isostructural series (Leban et al., 2007).
In order to investigate the structural relationships between ammonium salt forms of sulfonated azo dyes and their alkali-metal congeners, we herein present the crystal structures of ammonium salts of five azo anion species (Scheme 1). The structures of their Na-salt equivalents have already been reported (Kennedy et al., 2001, 2020; Dodds et al., 2017), as has the structure of one of their K equivalents (Kennedy et al., 2004). In order to complete the comparison we report herein the crystal structures of the remaining four K-salt equivalents.
2. Experimental
The Na salt of dye 3 was obtained from Fujifilm. The other dyes were synthesized as their Na salts using the well-known azo-coupling method (Alsantali et al., 2022; Kennedy et al., 2001). Na salts were converted to NH4 or K salts by reaction with a slight excess of either NH4Cl or KCl in warm water. Solutions were filtered to give clear aqueous solutions and then allowed to evaporate for 2 to 7 d. This gave yellow or yellow–orange crystals of the desired salt forms that were suitable for single-crystal FT–IR spectra were measured as KBr discs using a Nicolet Avatar 380 spectrometer. Raman data were measured from solids using a Reinshaw Ramascope with excitation at 785 nm. Aqueous UV–Vis spectra were measured using a Cary 300 Bio spectrophotometer and solid-state UV–Vis spectra were measured using a Phillips PU8749 spectrophotometer. Measurements on K1 were made at Station 9.8 of the Daresbury SRS. All other measurements were made using standard Rigaku Synergy-i (NH44) or Enraf–Nonius KappaCCD (all other structures) laboratory diffractometers equipped with CCD detectors.
2.1. Spectroscopic data
NH41, FT–IR (cm −1): 3421, 3267, 3088, 1598, 1501, 1280, 1193, 1040. Raman (cm−1): 1120, 1147, 1185, 1435, 1459, 1594. UV–Vis (λmax, nm): 348 (aq), 346 (solid).
NH42, FT–IR (cm −1): 1629, 1588, 1419, 1337, 1198, 1116, 1034, 999, 840, 804. Raman (cm−1): 239, 317, 348, 446, 836, 1036, 1122, 1161, 1197, 1324, 1375, 1419, 1591. UV–Vis (λmax, nm): 417 (aq), 334 (solid).
NH43, FT–IR (cm −1): 1634, 1603, 1501, 1398, 1383, 1275, 1193, 1116, 1034, 1004, 835. Raman (cm−1): peaks masked by fluorescence. UV–Vis (λmax, nm): 386 (aq), 332 (solid).
NH44, FT–IR (cm −1): 1598, 1511, 1403, 1213, 1116, 1075, 1024, 844, 814, 691. Raman (cm−1): 1034, 1115, 1143, 1197, 1315, 1356, 1387, 1419, 1441, 1589. UV–Vis (λmax, nm): 459 (aq), 418 (solid).
NH45, FT–IR (cm −1): 3405, 3190, 2366, 1597, 1495, 1423, 1177, 1136, 1034. Raman (cm−1): 1138, 1183, 1422, 1452 (somewhat masked by fluorescence). UV–Vis (λmax, nm): 348 (aq), 351 (solid).
K1, FT–IR (cm −1): 1593, 1460, 1372, 1178, 850, 717. Raman (cm−1): 628, 794, 922, 1102, 1121, 1147, 1158, 1309, 1396, 1435, 1590, 1607. UV–Vis (λmax, nm): 348 (aq), 334 (solid).
K2, FT–IR (cm −1): 3472, 3390, 1593, 1469, 1372, 1198, 1121, 1039, 839, 803. Raman (cm−1): 1033, 1122, 1161, 1198, 1326, 1374, 1418, 1592. UV–Vis (λmax, nm): 430 (aq), 336 (solid).
K3, FT–IR (cm −1): 1644, 1460, 1372, 1193, 1116, 1029, 839, 716. Raman (cm−1): 780, 921, 1036, 1120, 1152, 1427, 1588. UV–Vis (λmax, nm): 387 (aq), 345 (solid).
K4, FT–IR (cm −1): 1597, 1515, 1382, 1351, 1316, 1259, 1223, 1182, 1116, 1049, 1003. Raman (cm−1): 739, 1032, 1117, 1143, 1195, 1315, 1355, 1392, 1421, 1440. UV–Vis (λmax, nm): 458 (aq), 413 (solid).
K5, FT–IR (cm −1): 3390, 3078, 1603, 1501, 1383, 1188, 1034, 845. Raman (cm−1): 1136, 1169, 1185, 1424, 1454 (somewhat masked by fluorescence). UV–Vis (λmax, nm): 347 (aq), 348 (solid).
2.2. Refinement
Crystal data, data collection and structure . For K4, the azobenzene core of one of the two crystallographically independent dye anions was treated as disordered over two sites. In a similar way, one of the four independent SO3 groups of K3 was also treated as disordered over two sites, a rotation about the C—S bond giving alternative positions for the three O atoms. In both cases, appropriate restraints and constraints on the displacement parameters were added so as to ensure that the structures approximated normal behaviour. Finally, one water molecule of NH44 was modelled as rotationally disordered about atom O2W so that the water molecule has three independent H-atom sites. Where possible, H atoms attached to O or to N atoms were positioned as found in difference syntheses and refined freely and isotropically. Where riding models were required, X—H bond lengths were set at 0.88 (1) Å. All H atoms bound to C atoms were included in riding models, with C—H = 0.95 or 0.99 Å for CH and CH2 groups, respectively. For all H atoms in riding models, Uiso(H) values were set to 1.2Ueq of the parent atom.
details are summarized in Table 13. Results and discussion
All structures discussed are of crystal samples obtained from aqueous recrystallizations. Aqueous conditions were chosen to best reflect normal synthesis and usage of sulfonated azo dyes. It is possible to dry the hydrate structures described to give anhydrous materials. However, no polymorph screen has been attempted and so the existence of other forms is entirely likely. Selected crystallographic and and selected geometric parameters are given in Tables 2 to 14. Representations of the crystal structures of the ammonium salt forms NH41, NH42, NH43, NH44 and NH45 are given in Figs. 1 to 5. Both the phenol derivatives NH41 and NH45 are simple anhydrous salts with an NH4+ cation and an azo anion in the The other species are all hydrated forms as shown in Table 15. Additionally, both NH42 and NH44 are Z′ = 2 structures with two cation/anion pairs per as well as their accompanying water molecules. The bond lengths about the azo chromophores are in good agreement with those described for s-block metal salts of similar azo anions (Kennedy et al., 2001, 2020). The N=N bonds range from 1.254 (3) to 1.275 (2) Å, whilst the C—N bonds show ranges of 1.423 (2)–1.439 (2) and 1.396 (2)–1.425 (3) Å for the bonds involving the C atoms of the sulfonated and nonsulfonated rings, respectively. The generally shorter bonds of the latter are due to resonance with the OH and amine substituents. It is noteworthy that it is NH42 that displays both the longest N=N bond and the shortest N—C bond. The intramolecular O—H⋯N hydrogen bonding of NH42 raises the possibility of in this species and, although the electron density shows that the compound clearly exists largely as the azo tautomer, the bond lengths observed tend to reflect a small contribution from the alternative hydrazone tautomer. [See Kennedy et al. (2020) for a detailed discussion of factors that influence bond lengths and hence colour in similar azo dyes, and Yatsenko et al. (2024) for a discussion on azo/hydrazone in solid-state arylazo compounds.] Most of the azo anions have planar conformations, with angles between the planes of the aromatic rings ranging from 2.23 (9) to 12.32 (11)°. Despite this, the azo group does form a small step between the two parallel ring planes [e.g. in NH41, atom N2 lies 0.473 (5) Å out of the plane defined by atoms C1–C6]. The exception is the anion of NH43, which adopts a twisted conformation with an angle of 58.76 (11)° between the planes of its two aromatic rings. This out-of-plane twist in the solid state should alter the resonance through the azobenzene fragment and may contribute to the relatively large difference found between the solution-state and solid-state λmax values (386 versus 332 nm). It has previously been shown for s-block metal salt forms that the planar or twisted conformation of ortho-sulfonated azo anions correlates with the packing motifs observed. Thus, twisted azo species gave structures with a simple alternating layer structure, i.e. layers of organic anions alternating with hydrophilic layers containing the cations and water molecules. In contrast, planar azo anions gave structures with organic bilayers (Kennedy et al., 2009). This is not observed here; all the ammonium salts of the para- and meta-sulfonated anions 1 to 5 give simple layering structures with no bilayers, irrespective of the planarity of the anion (see Figs. 6 and 7 for examples).
parameters are given in Table 1
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Each H atom of every NH4+ cation acts as a hydrogen-bond donor to at least one O atom. There are no NH4-to-N hydrogen-bonding interactions. From Tables 2 to 6 and the summary Table 15, it can be seen that of the 28 independent N—H donors of the ammonium groups, 10 form bifurcated hydrogen bonds and two (atoms H8N of NH42 and H1N of NH45) interact with three separate O-atom acceptors. Most ammonium cations interact with six O atoms, but one (that containing atom N4 of structure NH44) has a of 5 and one (containing atom N3 of NH45) has a of 7. In all five structures, the majority of the ammonium cation hydrogen-bond interactions are with the O atoms of the formally negatively charged SO3 groups. For the anhydrous species NH41 and NH45, the ammonium ions also donate hydrogen bonds to the phenol OH groups; thus, hydrogen bonding from ammonium to both the SO3 head and the OH tail of the azo anions leads to the anions bridging between the inorganic/hydrophilic layers of the packing structures (Fig. 6). The hydrates NH42 and NH43 have no direct ammonium-to-tail-group hydrogen-bond interactions; instead, the water molecules act as intermediaries or bridges and accept/donate hydrogen bonds from both ammonium and tail groups. Thus, for these hydrate species, interactions between the hydrophobic and hydrophilic layers of the packing structure is via the water molecules. Despite featuring a lower cation in hydrate NH44, the cations donate hydrogen bonds to all of the different types of acceptor groups available, i.e. to the SO3 heads, to the OH groups of the tail and to bridging water molecules.
As they are situated at the centre of the hydrophobic layers, none of the –N=N– chromophore units take part in intermolecular hydrogen bonding. Indeed, the azo groups of NH41, NH43 and NH44 have no intermolecular contacts less than the sum of the van der Waals radii. NH45 is the only species of the five to show face-to-face π-contacts between the azobenzene units, with closest N2⋯C4 and C7⋯C3 contact distances of 3.160 (4) and 3.352 (4) Å, respectively. This forms the stacking motif seen extending parallel to the c axis in Fig. 8. In NH42, the ortho-OH substituent of one of the independent azo anions of the approaches the azo group of the other anion [O10⋯N1 = 3.052 (2) Å], creating dimeric pairs of anions (Fig. 9).
The structure of K2 was reported by Kennedy et al. (2004). Here, we report the remaining K-salt structures of azo anions 1 to 5. Figs. 9 to 13 show the fundamental features of these structures and selected geometric parameters are given in Table 7 to 14. K5 is anhydrous and a Z′ = 1 structure, but all other K salts were isolated as hydrates and have Z′ = 2 (or 4 for K3); see Table 15 for a summary of these and other structural features. Values for the disordered anion of K4 have been excluded from the geometric discussion below. The azo N=N bond lengths range from 1.258 (3) to 1.276 (3) Å, with the long value again found for the salt of 2 with its intramolecular O—H⋯N hydrogen bond and the possibility of The C—N bonds range from 1.420 (3) to 1.442 (4) and from 1.397 (3) to 1.432 (4) Å for the bonds to the sulfonated heads and to the phenol/amine tails, respectively. Again, it is K2 that presents the most different bond lengths. All these bond lengths are similar to those found for the NH4 salts, above, and for related sulfonated azo salt forms (Kennedy et al., 2020). Most azo anions have planar geometries [angles between ring planes = 0.93 (7) to 8.15 (22)°], with the exception of K1, where the two independent azo anions are both twisted [angles between ring planes = 43.15 (7) and 40.48 (8)°]. This contrasts with the ammonium salt structures, where all species were planar except for the twisted NH43. As with the NH4 species, all five K structures both planar and twisted have simple layered packing systems with layers of hydrophilic/inorganic species (K and water) alternating with layers of a hydrophobic/organic nature (azobenzene) (see Fig. 14 for an example).
Each K centre has a ), with all bonds from K being to O atoms. All K centres interact with SO3 groups and, where present, with water molecules. In K1, K4 and the anhydrous K5, there are also bonds formed between K and the OH groups of the tails of the azo anions. No such K-to-tail bonds are formed to the OH groups of K2 or to the NH2 groups of K3, instead these form only hydrogen bonds (Table 10). This throws up a similarity to the NH4 structures, where no direct NH4-to-tail hydrogen bond was found for NH42 or NH43, despite such bonds existing in all other compounds. As would be expected from the positions of the sulfonate groups and the nature of the cation, all five potassium salts form structures described elsewhere as class three `higher connectivity' azo colourant structures (Kennedy et al., 2004). Structures K1 and K5 both form three-dimensional coordination polymers, with K—O bonds (K-to-SO3 in K5 and both K-to-SO3 and K-to-OH2 in K1) forming bridges between K centres and allowing propagation of the polymer in two dimensions, whilst the third dimension features bridging between K centres through the body of the azo ion and hence utilizing both the head and tail functional groups of the azo anions (Fig. 14). Despite also featuring bridges between K centres via head-to-tail contacts with the azo anion, K4 is only a two-dimensional coordination polymer. Here, SO3 and OH2 bridges between K centres lead only to discrete K4 tetramers and it is only the through-azo head-to-tail interactions that allow the coordination polymer to propagate parallel to the b and c directions (Fig. 15). With no interaction with the amine tail of the azo anion, K3 displays a two-dimensional coordination polymer structure based solely on SO3 and OH2 bridges between K centres. Here, the polymeric structure propagates parallel to the a and b directions (Fig. 16). K2 also does not feature any K-to-tail interactions and here only a one-dimensional coordination polymer is formed. SO3 and OH2 bridges between K centres leads to a polymer that propagates parallel to the crystallographic a direction (Fig. 17).
of 7 or 8 (see Table 15The structures of the five Na salt equivalents of 1 to 5 crystallized from water solutions are all available from the literature (Kennedy et al., 2001, 2020; Dodds et al., 2017). As summarized in Table 15, Na1 forms a one-dimensional coordination polymer, whilst the other four Na structures all form two-dimensional coordination polymers. All Na centres are six-coordinate, except for those in Na4, which are seven-coordinate. All Na centres bond to O atoms of the sulfonate groups and to water ligands. Na1 and Na2 do not form bonds from Na to the tail phenol groups, but the other three structures do form Na-to-tail bonds to N or to O atoms. The azo anions that form bonds to Na with their tail groups are thus different from those that interact with K or with NH4, as described above. The generally lower coordination numbers of the Na salts (6 or 7) as compared to the K salts (7 or 8) seems to be reflected in a similarly generally lower dimensionality of coordination polymers (one- or two-dimensional for Na, and one- to three-dimensional for K), but this is not a hard and fast rule. This is shown by comparing Na2 with K2, where Na has a of 6 versus 7 for K, but where the Na compound is a two-dimensional coordination polymer and the K compound only one-dimensional.
Comparing the unit-cell dimensions given in Table 15, it can clearly be seen that there are two isostructural pairs. The and unit-cell dimensions of NH42 match those of K2 and there is a similar match between NH45 and K5. Based on the unit-cell dimensions, none of the Na species are isostructural with any NH4 or K salt form. For the NH45 and K5 pair, all generalized structural descriptors (such as Z′, hydration state and the of the cation) are identical, as would be expected for a truly isostructural pair. However, the descriptors given for the NH42 and K2 pair in Table 15, whilst mostly identical, do differ with respect to the of the cation. The NH4 ions are given as making six interactions each, whilst the K centres are given as each making seven interactions. Investigation shows that this difference is not just a case of an inappropriate cut-off distance being used to calculate potential hydrogen-bonding interactions. For example, the `extra' seventh bond for atom K1 is an interaction with a sulfonate O atom. The closest sulfonate O atom to the equivalent ammonium ion in NH42, that has not already been accounted for as a hydrogen-bonding interaction, gives an N⋯O distance of over 4.2 Å, which is clearly too long for a hydrogen bond; see Table 3 for genuine N⋯O hydrogen-bond distances. Thus, although NH42 and K2 have similar unit-cell dimensions and similar compositions, small changes in the orientations of the sulfonate groups and the cations allow the ammonium and potassium cations to make somewhat different interactions from each other. The ability of isostructural structures to tolerate small changes within a given packing motif has been discussed recently by Bombicz (2024).
Expanding from the 15 structures of Table 15 to other literature structures, of the five azo anions studied here, only 3 has had the structure of its Rb salt form reported (Kennedy et al., 2004). The structure of Rb3 is found to be isostructural with that of NH43 (compare C2/c, 35.256, 7.738, 10.674 Å and 99.88° with the values given for NH43 in Table 1). As with NH42 and K2 above, all structural descriptors match, except for the Rb cation having a higher than the ammonium cation (8 versus 6). Other sulfonated monoazo NH4 salt form structures available are those of diammonium Orange G tetrahydrate and of the nitrile-substituted [NH4][O3S(C6H4)NN(C6H4)NHCH2CH2CN]·H2O (Ojala et al., 1994; Astbury et al., 2013). For these azo anions, the only available comparisons for the ammonium salts are the Na and mixed Na/K and Na/Rb salt forms of Orange G and the Na salt of the nitrile (Kennedy et al., 2006; Astbury et al., 2013). Based on unit-cell dimensions, the nitrile shows no isostructurality. There are however similarities, if not exact matches, between the unit cells of the Orange G structures of Table 16; see comments below for a fuller discussion of these features.
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The `crystal packing similarity' tool available within Mercury (Macrae et al., 2020) can be used to find packing similarity regardless of any matches in the unit-cell dimension. For instance, it has been used to find similarities in the packing behaviour of dopamine and tyramine fragments in the salt and hydrate forms of these active pharmaceutical ingredients (APIs), regardless of counter-ions, solvents and the identity and protonation state of the phenylethylamine fragment itself (Kennedy et al., 2023). This tool was applied to the 15 structures of Table 15 and to the other relevant NH4, Na, K, Rb, Cs and Ag salt structures found in the Cambridge Structural Database (CSD; Groom et al., 2016). The packing analysis was set up to examine packed fragments consisting of 15 sulfonated azo molecular units. Other components (cations and solvent molecules) were ignored. Indeed, in order to simplify the definition of a `molecular fragment', all metal ions were deleted from the files used for these analyses. Only the three pairs previously identified as being isostructural from their unit-cell dimensions (i.e. NH42 and K2, NH45 and K5, and NH43 and Rb3) had azo anion packing that matched at a 15/15 level with a 20% tolerance allowed. However, it was found that NH43 also matched at a 13/15 level with the isostructural pair of structures having CSD refcodes BAHNAC and BAHNIK (Dodds et al., 2017). Surprisingly, these two structures are not forms of the para-NH2-substituted anion 3, but correspond to the Na and Ag salt forms of the meta-OH-substituted anion 5. Further investigation of these structures reveals that it is their layered natures that lead to this partial match. Those azo fragments that lie within a single hydrophobic layer of NH43 match well with their equivalents in Na5 and Ag5, despite the differences in SO3 position and the different chemical natures of the NH2/OH tail groups. However, the azo fragments within the neighbouring hydrophobic layers do not match, being rotated with respect to one another (Fig. 18). A similar situation was found for the Orange G salts of Table 16. As is perhaps suggested by the differences in the unit-cell parameters, none of the metal salt forms were truly isostructural with the ammonium salt of Orange G. However, both the mixed Na/K and Na/Rb species matched the ammonium salt at a 12/15 level and the pure Na species matched at a 9/15 level. As with the case for 3 above, the matches within one organic layer are reasonable, but the structures do not match well when neighbouring layers are considered. Finally, examining the structures of Table 15 it can be seen that NH41 and K1 have somewhat similar a and b dimensions, whilst c is approximately doubled. Despite this, investigations showed that these structures did not show any significant similarity in the packing for the azo anions.
4. Summary
Five new structures of ammonium salt forms of sulfonated azo dyes have been presented and compared to the equivalent Na and K salt structures. Despite being based on ammonium-to-sulfonate hydrogen bonds rather than metal-ion-to-sulfonate bonds, the ammonium salt forms are found to have structural types that are in many ways similar to those found for heavier alkali-metal ions (Na, K and Rb). The ammonium structures have the same simple alternating hydrophobic/hydrophilic layer structures described earlier for s-block metal salt forms of para- and meta-sulfonated azo dyes (Kennedy et al., 2004) and do not show the more complicated layering motifs seen elsewhere (Kennedy et al., 2009). Two of the five ammonium structures (NH42 and NH45) show isostructurality with their equivalent potassium structures. For anion 3, the ammonium and Rb salt forms are also found to be isostructural, although unfortunately no other Rb salt structures are available for comparison. For the isostructural pair of 5, all structural descriptors are very similar, but for the 2 and 3 pairs there are small differences in, for example, the rotation of the sulfonate groups that allow the ammonium cations to make less formal contacts than do the K or Rb ions. No sodium salt is found to be isostructural with an ammonium salt, but use of the `crystal packing similarity' tool within Mercury did highlight that the azo anions of NH43 do adopt similar packing to the chemically different azo anions of both Na5 and Ag5, although this similarity only holds within a single hydrophobic layer, with neighbouring layers behaving differently. The ammonium salt of Orange G shows similar single-layer-matching behaviour with its Na and mixed Na/K and Na/Rb salt forms. Overall there is thus a high propensity for ammonium salt forms of sulfonated azo dyes to be isostructural with the equivalent K or Rb forms, a propensity which is aided by small amounts of flexibility in the structures that allows for the different coordinating abilities of the cations. Little evidence is found for isostructural relationships between the salt forms of sulfonated azo dyes of ammonium salts and the equivalent sodium salts. Here, the smaller radius of the Na+ ion is perhaps hard to offset against the lower of sodium. However, the similarity of anion packing found, for instance, within single layers for NH43 (and hence Rb3) with Na5 and Ag5 may indicate that isostructurality is possible and may be found if a larger sample of structures was available.
Supporting information
https://doi.org/10.1107/S2053229624001293/dg3051sup1.cif
contains datablocks NH41, NH42, NH43, NH44, NH45, K1, K3, K4, K5, global. DOI:Structure factors: contains datablock NH41. DOI: https://doi.org/10.1107/S2053229624001293/dg3051NH41sup2.hkl
Structure factors: contains datablock NH42. DOI: https://doi.org/10.1107/S2053229624001293/dg3051NH42sup3.hkl
Structure factors: contains datablock NH43. DOI: https://doi.org/10.1107/S2053229624001293/dg3051NH43sup4.hkl
Structure factors: contains datablock NH44. DOI: https://doi.org/10.1107/S2053229624001293/dg3051NH44sup5.hkl
Structure factors: contains datablock NH45. DOI: https://doi.org/10.1107/S2053229624001293/dg3051NH45sup6.hkl
Structure factors: contains datablock K1. DOI: https://doi.org/10.1107/S2053229624001293/dg3051K1sup7.hkl
Structure factors: contains datablock K3. DOI: https://doi.org/10.1107/S2053229624001293/dg3051K3sup8.hkl
Structure factors: contains datablock K4. DOI: https://doi.org/10.1107/S2053229624001293/dg3051K4sup9.hkl
Structure factors: contains datablock K5. DOI: https://doi.org/10.1107/S2053229624001293/dg3051K5sup10.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2053229624001293/dg3051NH41sup11.cml
Supporting information file. DOI: https://doi.org/10.1107/S2053229624001293/dg3051NH42sup12.cml
Supporting information file. DOI: https://doi.org/10.1107/S2053229624001293/dg3051NH43sup13.cml
Supporting information file. DOI: https://doi.org/10.1107/S2053229624001293/dg3051NH44sup14.cml
Supporting information file. DOI: https://doi.org/10.1107/S2053229624001293/dg3051NH45sup15.cml
NH4+·C12H9N2O4S− | F(000) = 308 |
Mr = 295.31 | Dx = 1.561 Mg m−3 |
Monoclinic, P21 | Cu Kα radiation, λ = 1.54184 Å |
a = 5.8163 (1) Å | Cell parameters from 12251 reflections |
b = 6.9218 (1) Å | θ = 2.8–71.4° |
c = 15.6295 (2) Å | µ = 2.48 mm−1 |
β = 93.354 (1)° | T = 100 K |
V = 628.15 (2) Å3 | Broken tablet, yellow |
Z = 2 | 0.22 × 0.12 × 0.06 mm |
Rigaku Synergy-i diffractometer | 2336 reflections with I > 2σ(I) |
Radiation source: microsource tube | Rint = 0.054 |
ω scans | θmax = 71.8°, θmin = 2.8° |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2019) | h = −7→7 |
Tmin = 0.859, Tmax = 1.000 | k = −8→8 |
10144 measured reflections | l = −18→19 |
2345 independent reflections |
Refinement on F2 | H atoms treated by a mixture of independent and constrained refinement |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0492P)2 + 0.3416P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.029 | (Δ/σ)max < 0.001 |
wR(F2) = 0.084 | Δρmax = 0.26 e Å−3 |
S = 1.08 | Δρmin = −0.33 e Å−3 |
2345 reflections | Extinction correction: SHELXL2018 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
203 parameters | Extinction coefficient: 0.0059 (10) |
1 restraint | Absolute structure: Refined as an inversion twin. |
Hydrogen site location: mixed | Absolute structure parameter: 0.00 (2) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refined as a 2-component inversion twin. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.35361 (10) | 0.29158 (10) | 0.12661 (3) | 0.0123 (2) | |
O1 | 0.4130 (4) | 0.4665 (3) | 0.08089 (13) | 0.0173 (5) | |
O2 | 0.4932 (4) | 0.1276 (3) | 0.10136 (13) | 0.0182 (5) | |
O3 | 0.1084 (3) | 0.2481 (4) | 0.12008 (12) | 0.0230 (6) | |
O4 | 1.1582 (3) | 0.3583 (3) | 0.85733 (13) | 0.0162 (5) | |
N1 | 0.6429 (4) | 0.3448 (4) | 0.49689 (15) | 0.0138 (5) | |
N2 | 0.8571 (4) | 0.3609 (4) | 0.51273 (15) | 0.0138 (5) | |
N3 | −0.2044 (4) | 0.3231 (4) | −0.01967 (16) | 0.0159 (6) | |
C1 | 0.4303 (5) | 0.3311 (4) | 0.23627 (17) | 0.0134 (6) | |
C2 | 0.2832 (4) | 0.2720 (5) | 0.29837 (16) | 0.0127 (5) | |
H2 | 0.134187 | 0.223460 | 0.282173 | 0.015* | |
C3 | 0.3571 (4) | 0.2850 (5) | 0.38439 (15) | 0.0127 (5) | |
H3 | 0.256899 | 0.248354 | 0.427438 | 0.015* | |
C4 | 0.5780 (5) | 0.3516 (4) | 0.40746 (18) | 0.0130 (6) | |
C5 | 0.7218 (5) | 0.4191 (4) | 0.34458 (17) | 0.0126 (6) | |
H5 | 0.868874 | 0.471605 | 0.360730 | 0.015* | |
C6 | 0.6473 (5) | 0.4084 (4) | 0.25935 (18) | 0.0130 (6) | |
H6 | 0.743184 | 0.453318 | 0.216382 | 0.016* | |
C7 | 0.9258 (5) | 0.3512 (4) | 0.60152 (17) | 0.0123 (6) | |
C8 | 1.1468 (5) | 0.4181 (4) | 0.62395 (17) | 0.0132 (6) | |
H8 | 1.243125 | 0.460308 | 0.580605 | 0.016* | |
C9 | 1.2272 (5) | 0.4236 (4) | 0.70920 (17) | 0.0135 (6) | |
H9 | 1.376389 | 0.472961 | 0.724518 | 0.016* | |
C10 | 1.0875 (5) | 0.3560 (4) | 0.77230 (17) | 0.0127 (6) | |
C11 | 0.8704 (4) | 0.2800 (5) | 0.74958 (16) | 0.0142 (5) | |
H11 | 0.778425 | 0.229619 | 0.792613 | 0.017* | |
C12 | 0.7882 (4) | 0.2777 (5) | 0.66469 (16) | 0.0139 (5) | |
H12 | 0.639877 | 0.226653 | 0.649335 | 0.017* | |
H1H | 1.268 (8) | 0.444 (8) | 0.861 (3) | 0.037 (12)* | |
H1N | −0.260 (7) | 0.214 (7) | −0.038 (2) | 0.018 (9)* | |
H2N | −0.114 (7) | 0.362 (6) | −0.060 (3) | 0.025 (10)* | |
H3N | −0.122 (8) | 0.301 (8) | 0.027 (3) | 0.043 (12)* | |
H4N | −0.312 (9) | 0.414 (8) | −0.008 (3) | 0.051 (14)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0123 (3) | 0.0150 (3) | 0.0093 (3) | 0.0001 (3) | −0.0010 (2) | 0.0009 (3) |
O1 | 0.0233 (10) | 0.0151 (11) | 0.0137 (9) | 0.0022 (9) | 0.0038 (8) | 0.0041 (8) |
O2 | 0.0259 (11) | 0.0153 (11) | 0.0131 (10) | 0.0039 (9) | −0.0018 (8) | −0.0026 (8) |
O3 | 0.0152 (10) | 0.0391 (16) | 0.0142 (9) | −0.0059 (10) | −0.0029 (7) | 0.0036 (10) |
O4 | 0.0157 (10) | 0.0205 (11) | 0.0121 (9) | −0.0028 (9) | −0.0014 (7) | −0.0014 (8) |
N1 | 0.0132 (11) | 0.0146 (13) | 0.0133 (11) | −0.0003 (9) | −0.0003 (9) | −0.0014 (9) |
N2 | 0.0137 (11) | 0.0146 (11) | 0.0130 (11) | −0.0006 (10) | −0.0003 (9) | −0.0005 (9) |
N3 | 0.0156 (11) | 0.0176 (16) | 0.0142 (12) | −0.0015 (10) | −0.0007 (10) | 0.0003 (10) |
C1 | 0.0140 (12) | 0.0154 (16) | 0.0108 (12) | 0.0033 (10) | 0.0000 (9) | −0.0001 (10) |
C2 | 0.0114 (11) | 0.0126 (14) | 0.0139 (12) | 0.0005 (12) | −0.0011 (9) | −0.0001 (12) |
C3 | 0.0139 (11) | 0.0117 (12) | 0.0128 (11) | 0.0023 (13) | 0.0034 (9) | 0.0006 (12) |
C4 | 0.0151 (13) | 0.0130 (13) | 0.0109 (12) | 0.0015 (11) | 0.0014 (10) | −0.0009 (10) |
C5 | 0.0118 (12) | 0.0107 (14) | 0.0154 (13) | −0.0002 (11) | 0.0006 (10) | −0.0009 (11) |
C6 | 0.0124 (12) | 0.0119 (14) | 0.0150 (13) | −0.0017 (11) | 0.0036 (10) | 0.0010 (11) |
C7 | 0.0130 (12) | 0.0127 (14) | 0.0112 (12) | 0.0012 (11) | 0.0002 (10) | −0.0019 (10) |
C8 | 0.0131 (12) | 0.0122 (14) | 0.0144 (13) | 0.0007 (11) | 0.0026 (10) | −0.0006 (11) |
C9 | 0.0094 (12) | 0.0152 (15) | 0.0158 (13) | −0.0012 (11) | 0.0002 (10) | −0.0016 (12) |
C10 | 0.0162 (13) | 0.0114 (13) | 0.0105 (12) | 0.0017 (11) | −0.0001 (10) | −0.0021 (10) |
C11 | 0.0144 (12) | 0.0151 (14) | 0.0135 (11) | −0.0001 (13) | 0.0025 (9) | 0.0008 (13) |
C12 | 0.0132 (12) | 0.0137 (14) | 0.0147 (12) | −0.0017 (13) | 0.0007 (9) | −0.0017 (13) |
S1—O3 | 1.456 (2) | C3—C4 | 1.392 (4) |
S1—O1 | 1.457 (2) | C3—H3 | 0.9500 |
S1—O2 | 1.463 (2) | C4—C5 | 1.407 (4) |
S1—C1 | 1.767 (3) | C5—C6 | 1.379 (4) |
O4—C10 | 1.368 (3) | C5—H5 | 0.9500 |
O4—H1H | 0.87 (5) | C6—H6 | 0.9500 |
N1—N2 | 1.261 (3) | C7—C8 | 1.392 (4) |
N1—C4 | 1.427 (4) | C7—C12 | 1.402 (4) |
N2—C7 | 1.423 (4) | C8—C9 | 1.386 (4) |
N3—H1N | 0.86 (4) | C8—H8 | 0.9500 |
N3—H2N | 0.88 (4) | C9—C10 | 1.395 (4) |
N3—H3N | 0.86 (5) | C9—H9 | 0.9500 |
N3—H4N | 0.91 (5) | C10—C11 | 1.394 (4) |
C1—C2 | 1.392 (4) | C11—C12 | 1.384 (3) |
C1—C6 | 1.399 (4) | C11—H11 | 0.9500 |
C2—C3 | 1.390 (3) | C12—H12 | 0.9500 |
C2—H2 | 0.9500 | ||
O3—S1—O1 | 113.38 (13) | C5—C4—N1 | 124.1 (3) |
O3—S1—O2 | 112.19 (14) | C6—C5—C4 | 119.4 (3) |
O1—S1—O2 | 111.15 (12) | C6—C5—H5 | 120.3 |
O3—S1—C1 | 106.90 (12) | C4—C5—H5 | 120.3 |
O1—S1—C1 | 107.07 (13) | C5—C6—C1 | 119.8 (3) |
O2—S1—C1 | 105.62 (12) | C5—C6—H6 | 120.1 |
C10—O4—H1H | 105 (3) | C1—C6—H6 | 120.1 |
N2—N1—C4 | 113.0 (2) | C8—C7—C12 | 120.0 (2) |
N1—N2—C7 | 113.9 (2) | C8—C7—N2 | 115.6 (2) |
H1N—N3—H2N | 105 (4) | C12—C7—N2 | 124.4 (2) |
H1N—N3—H3N | 108 (4) | C9—C8—C7 | 120.4 (2) |
H2N—N3—H3N | 109 (4) | C9—C8—H8 | 119.8 |
H1N—N3—H4N | 115 (4) | C7—C8—H8 | 119.8 |
H2N—N3—H4N | 112 (4) | C8—C9—C10 | 119.5 (3) |
H3N—N3—H4N | 107 (4) | C8—C9—H9 | 120.2 |
C2—C1—C6 | 121.0 (2) | C10—C9—H9 | 120.2 |
C2—C1—S1 | 120.0 (2) | O4—C10—C11 | 117.9 (2) |
C6—C1—S1 | 118.8 (2) | O4—C10—C9 | 121.9 (3) |
C3—C2—C1 | 119.2 (2) | C11—C10—C9 | 120.2 (2) |
C3—C2—H2 | 120.4 | C12—C11—C10 | 120.4 (2) |
C1—C2—H2 | 120.4 | C12—C11—H11 | 119.8 |
C2—C3—C4 | 120.0 (2) | C10—C11—H11 | 119.8 |
C2—C3—H3 | 120.0 | C11—C12—C7 | 119.4 (2) |
C4—C3—H3 | 120.0 | C11—C12—H12 | 120.3 |
C3—C4—C5 | 120.4 (3) | C7—C12—H12 | 120.3 |
C3—C4—N1 | 115.5 (2) | ||
C4—N1—N2—C7 | −179.0 (2) | C4—C5—C6—C1 | 0.1 (4) |
O3—S1—C1—C2 | 15.9 (3) | C2—C1—C6—C5 | 2.8 (4) |
O1—S1—C1—C2 | 137.7 (2) | S1—C1—C6—C5 | −172.3 (2) |
O2—S1—C1—C2 | −103.8 (2) | N1—N2—C7—C8 | −163.7 (3) |
O3—S1—C1—C6 | −169.0 (2) | N1—N2—C7—C12 | 17.3 (4) |
O1—S1—C1—C6 | −47.2 (3) | C12—C7—C8—C9 | −3.9 (4) |
O2—S1—C1—C6 | 71.3 (3) | N2—C7—C8—C9 | 177.0 (3) |
C6—C1—C2—C3 | −2.0 (4) | C7—C8—C9—C10 | 1.9 (4) |
S1—C1—C2—C3 | 173.0 (2) | C8—C9—C10—O4 | −179.9 (3) |
C1—C2—C3—C4 | −1.7 (5) | C8—C9—C10—C11 | 1.3 (4) |
C2—C3—C4—C5 | 4.5 (5) | O4—C10—C11—C12 | 178.7 (3) |
C2—C3—C4—N1 | −175.2 (3) | C9—C10—C11—C12 | −2.4 (5) |
N2—N1—C4—C3 | 163.8 (3) | C10—C11—C12—C7 | 0.4 (5) |
N2—N1—C4—C5 | −16.0 (4) | C8—C7—C12—C11 | 2.7 (4) |
C3—C4—C5—C6 | −3.8 (4) | N2—C7—C12—C11 | −178.3 (3) |
N1—C4—C5—C6 | 176.0 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H4N···O2i | 0.91 (5) | 2.30 (5) | 2.940 (4) | 127 (4) |
N3—H4N···O1ii | 0.91 (5) | 2.21 (5) | 2.969 (3) | 141 (4) |
N3—H3N···O3 | 0.86 (5) | 1.96 (5) | 2.808 (3) | 170 (4) |
N3—H1N···O1iii | 0.86 (4) | 2.03 (5) | 2.889 (4) | 176 (4) |
N3—H2N···O4iv | 0.88 (4) | 2.10 (4) | 2.946 (3) | 159 (4) |
O4—H1H···O2v | 0.87 (5) | 1.95 (5) | 2.802 (3) | 167 (4) |
Symmetry codes: (i) −x, y+1/2, −z; (ii) x−1, y, z; (iii) −x, y−1/2, −z; (iv) x−1, y, z−1; (v) −x+2, y+1/2, −z+1. |
NH4+·C12H9N2O5S−·2H2O | Z = 4 |
Mr = 347.34 | F(000) = 728 |
Triclinic, P1 | Dx = 1.506 Mg m−3 |
a = 8.2876 (1) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.6404 (1) Å | Cell parameters from 8081 reflections |
c = 17.4834 (3) Å | θ = 1.0–29.1° |
α = 89.734 (1)° | µ = 0.25 mm−1 |
β = 84.793 (1)° | T = 123 K |
γ = 86.146 (1)° | Rhomb, yellow-orange |
V = 1531.91 (4) Å3 | 0.42 × 0.40 × 0.10 mm |
Enraf–Nonius KappaCCD diffractometer | Rint = 0.021 |
Radiation source: sealed tube | θmax = 29.1°, θmin = 1.2° |
phi and ω scans | h = −11→11 |
15978 measured reflections | k = −14→14 |
8209 independent reflections | l = −23→23 |
6704 reflections with I > 2σ(I) |
Refinement on F2 | 1 restraint |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.036 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.094 | w = 1/[σ2(Fo2) + (0.0395P)2 + 0.8626P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.001 |
8209 reflections | Δρmax = 0.58 e Å−3 |
495 parameters | Δρmin = −0.41 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.62192 (4) | 0.04619 (3) | 0.10240 (2) | 0.01709 (8) | |
S2 | 0.09636 (4) | 0.38246 (3) | 0.12364 (2) | 0.01713 (8) | |
O1 | 0.76850 (13) | −0.01171 (10) | 0.06027 (6) | 0.0214 (2) | |
O2 | 0.48499 (13) | −0.03156 (11) | 0.09970 (6) | 0.0271 (2) | |
O3 | 0.58719 (14) | 0.17567 (10) | 0.07836 (6) | 0.0260 (2) | |
O4 | 0.98516 (14) | 0.14681 (10) | 0.75672 (6) | 0.0219 (2) | |
O5 | 0.71395 (13) | −0.04078 (10) | 0.56317 (6) | 0.0222 (2) | |
O6 | 0.07572 (14) | 0.25449 (10) | 0.09790 (6) | 0.0242 (2) | |
O7 | 0.22672 (14) | 0.43876 (10) | 0.07644 (6) | 0.0250 (2) | |
O8 | −0.05487 (13) | 0.46083 (11) | 0.12893 (6) | 0.0270 (2) | |
O9 | 0.52842 (13) | 0.41871 (10) | 0.76776 (6) | 0.0218 (2) | |
O10 | 0.51487 (14) | 0.23392 (10) | 0.52554 (6) | 0.0245 (2) | |
O1W | −0.16671 (16) | 0.71210 (13) | 0.15040 (8) | 0.0322 (3) | |
O2W | 0.38515 (14) | 0.56714 (12) | 0.88010 (7) | 0.0275 (2) | |
O3W | 0.71337 (14) | 0.32285 (11) | 0.88635 (7) | 0.0260 (2) | |
O4W | 0.84097 (16) | −0.00710 (11) | 0.85537 (7) | 0.0255 (2) | |
N1 | 0.76041 (15) | 0.05814 (11) | 0.43032 (7) | 0.0187 (2) | |
N2 | 0.85430 (15) | 0.13819 (11) | 0.45120 (7) | 0.0193 (2) | |
N3 | 0.33504 (14) | 0.35053 (11) | 0.43444 (7) | 0.0176 (2) | |
N4 | 0.28336 (14) | 0.43660 (11) | 0.48284 (7) | 0.0174 (2) | |
N5 | 0.93365 (17) | 0.16781 (13) | −0.03240 (7) | 0.0194 (2) | |
N6 | −0.39612 (17) | 0.72023 (14) | 0.04186 (8) | 0.0233 (3) | |
C1 | 0.66330 (17) | 0.05333 (13) | 0.19978 (7) | 0.0162 (3) | |
C2 | 0.77120 (17) | 0.13898 (13) | 0.22148 (8) | 0.0192 (3) | |
H1 | 0.819914 | 0.193701 | 0.184416 | 0.023* | |
C3 | 0.80712 (18) | 0.14393 (13) | 0.29746 (8) | 0.0193 (3) | |
H2 | 0.880801 | 0.201593 | 0.312773 | 0.023* | |
C4 | 0.73336 (17) | 0.06287 (13) | 0.35112 (8) | 0.0179 (3) | |
C5 | 0.62652 (18) | −0.02228 (14) | 0.32902 (8) | 0.0201 (3) | |
H3 | 0.577284 | −0.076857 | 0.366013 | 0.024* | |
C6 | 0.59143 (18) | −0.02792 (14) | 0.25305 (8) | 0.0196 (3) | |
4H | 0.519150 | −0.086608 | 0.237650 | 0.023* | |
C7 | 0.88081 (17) | 0.13237 (13) | 0.52941 (8) | 0.0181 (3) | |
C8 | 0.98383 (18) | 0.21938 (14) | 0.55419 (8) | 0.0213 (3) | |
H5 | 1.030580 | 0.276831 | 0.518260 | 0.026* | |
C9 | 1.01927 (18) | 0.22375 (14) | 0.62985 (8) | 0.0207 (3) | |
H6 | 1.090060 | 0.283074 | 0.645886 | 0.025* | |
C10 | 0.94882 (17) | 0.13902 (13) | 0.68248 (8) | 0.0180 (3) | |
C11 | 0.84685 (17) | 0.05103 (13) | 0.65983 (8) | 0.0184 (3) | |
H8 | 0.800804 | −0.005918 | 0.696292 | 0.022* | |
C12 | 0.81178 (17) | 0.04618 (13) | 0.58317 (8) | 0.0175 (3) | |
C13 | 0.15837 (16) | 0.37139 (13) | 0.21753 (8) | 0.0166 (3) | |
C14 | 0.08726 (18) | 0.45338 (14) | 0.27459 (8) | 0.0219 (3) | |
H10 | 0.001186 | 0.512467 | 0.263835 | 0.026* | |
C15 | 0.14229 (18) | 0.44866 (14) | 0.34716 (8) | 0.0221 (3) | |
H11 | 0.094605 | 0.504738 | 0.386260 | 0.027* | |
C16 | 0.26783 (17) | 0.36126 (13) | 0.36236 (8) | 0.0169 (3) | |
C17 | 0.33736 (18) | 0.27771 (13) | 0.30555 (8) | 0.0195 (3) | |
H12 | 0.421320 | 0.217035 | 0.316760 | 0.023* | |
C18 | 0.28372 (17) | 0.28334 (13) | 0.23264 (8) | 0.0195 (3) | |
H13 | 0.331939 | 0.227749 | 0.193401 | 0.023* | |
C19 | 0.34935 (16) | 0.42642 (13) | 0.55348 (8) | 0.0162 (3) | |
C20 | 0.29766 (17) | 0.52133 (13) | 0.60747 (8) | 0.0188 (3) | |
H14 | 0.222998 | 0.587727 | 0.594106 | 0.023* | |
C21 | 0.35318 (18) | 0.52007 (14) | 0.67955 (8) | 0.0196 (3) | |
H15 | 0.314923 | 0.583618 | 0.716005 | 0.023* | |
C22 | 0.46707 (17) | 0.42355 (13) | 0.69833 (8) | 0.0172 (3) | |
C23 | 0.52292 (18) | 0.32983 (13) | 0.64569 (8) | 0.0189 (3) | |
H17 | 0.601645 | 0.266207 | 0.658768 | 0.023* | |
C24 | 0.46361 (17) | 0.32899 (13) | 0.57373 (8) | 0.0172 (3) | |
H1H | 0.939 (3) | 0.092 (2) | 0.7835 (12) | 0.037 (6)* | |
H2H | 0.708 (3) | −0.022 (2) | 0.5086 (15) | 0.062 (7)* | |
H3H | 0.477 (3) | 0.473 (2) | 0.7984 (13) | 0.042 (6)* | |
H4H | 0.464 (3) | 0.254 (2) | 0.4811 (15) | 0.060 (7)* | |
H1N | 1.013 (2) | 0.1347 (18) | −0.0556 (11) | 0.023 (5)* | |
H2N | 0.871 (3) | 0.109 (2) | −0.0084 (13) | 0.042 (6)* | |
H3N | 0.868 (3) | 0.218 (2) | −0.0635 (13) | 0.045 (6)* | |
H4N | 0.966 (3) | 0.216 (2) | 0.0036 (14) | 0.047 (6)* | |
H5N | −0.354 (3) | 0.663 (2) | 0.0065 (13) | 0.040 (6)* | |
H6N | −0.329 (3) | 0.7249 (19) | 0.0805 (13) | 0.040 (6)* | |
H7N | −0.495 (3) | 0.697 (2) | 0.0640 (13) | 0.042 (6)* | |
H8N | −0.412 (3) | 0.790 (2) | 0.0202 (13) | 0.043 (6)* | |
H1W | −0.123 (3) | 0.640 (3) | 0.1495 (14) | 0.055 (7)* | |
H2W | −0.131 (3) | 0.754 (2) | 0.1849 (15) | 0.055 (7)* | |
H3W | 0.403 (3) | 0.641 (2) | 0.8893 (14) | 0.050 (7)* | |
H4W | 0.2803 (12) | 0.566 (2) | 0.8824 (13) | 0.048 (6)* | |
H5W | 0.733 (3) | 0.400 (2) | 0.8992 (14) | 0.055 (7)* | |
H6W | 0.691 (3) | 0.330 (3) | 0.8338 (17) | 0.078 (9)* | |
H7W | 0.744 (3) | 0.0001 (19) | 0.8695 (12) | 0.031 (5)* | |
H8W | 0.868 (3) | −0.080 (2) | 0.8637 (13) | 0.048 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.01834 (17) | 0.01888 (16) | 0.01370 (15) | 0.00414 (13) | −0.00344 (12) | −0.00218 (12) |
S2 | 0.01813 (17) | 0.01791 (16) | 0.01587 (16) | −0.00119 (12) | −0.00427 (12) | −0.00132 (12) |
O1 | 0.0217 (5) | 0.0244 (5) | 0.0167 (5) | 0.0061 (4) | 0.0000 (4) | −0.0011 (4) |
O2 | 0.0231 (6) | 0.0357 (6) | 0.0236 (5) | −0.0038 (5) | −0.0060 (4) | −0.0062 (5) |
O3 | 0.0384 (6) | 0.0202 (5) | 0.0191 (5) | 0.0095 (5) | −0.0100 (5) | −0.0017 (4) |
O4 | 0.0276 (6) | 0.0249 (5) | 0.0145 (5) | −0.0060 (4) | −0.0055 (4) | −0.0014 (4) |
O5 | 0.0265 (6) | 0.0235 (5) | 0.0178 (5) | −0.0075 (4) | −0.0045 (4) | 0.0006 (4) |
O6 | 0.0331 (6) | 0.0195 (5) | 0.0216 (5) | −0.0045 (4) | −0.0096 (4) | −0.0020 (4) |
O7 | 0.0296 (6) | 0.0279 (6) | 0.0180 (5) | −0.0084 (5) | −0.0002 (4) | 0.0000 (4) |
O8 | 0.0236 (6) | 0.0316 (6) | 0.0261 (6) | 0.0074 (5) | −0.0099 (4) | −0.0045 (5) |
O9 | 0.0244 (5) | 0.0248 (5) | 0.0166 (5) | 0.0030 (4) | −0.0066 (4) | −0.0026 (4) |
O10 | 0.0310 (6) | 0.0225 (5) | 0.0192 (5) | 0.0092 (4) | −0.0058 (4) | −0.0052 (4) |
O1W | 0.0351 (7) | 0.0257 (6) | 0.0388 (7) | −0.0025 (5) | −0.0192 (6) | −0.0029 (5) |
O2W | 0.0237 (6) | 0.0269 (6) | 0.0318 (6) | −0.0001 (5) | −0.0027 (5) | −0.0081 (5) |
O3W | 0.0290 (6) | 0.0232 (6) | 0.0265 (6) | −0.0016 (5) | −0.0067 (5) | 0.0022 (4) |
O4W | 0.0249 (6) | 0.0235 (6) | 0.0275 (6) | −0.0009 (5) | 0.0009 (5) | 0.0017 (4) |
N1 | 0.0186 (6) | 0.0194 (6) | 0.0173 (6) | 0.0027 (5) | −0.0010 (5) | −0.0013 (4) |
N2 | 0.0188 (6) | 0.0196 (6) | 0.0189 (6) | 0.0018 (5) | −0.0002 (5) | 0.0001 (4) |
N3 | 0.0187 (6) | 0.0179 (6) | 0.0162 (5) | −0.0015 (5) | −0.0015 (4) | −0.0005 (4) |
N4 | 0.0164 (6) | 0.0188 (6) | 0.0172 (5) | −0.0022 (4) | −0.0011 (4) | −0.0008 (4) |
N5 | 0.0207 (6) | 0.0213 (6) | 0.0163 (6) | −0.0015 (5) | −0.0026 (5) | −0.0031 (5) |
N6 | 0.0210 (7) | 0.0251 (7) | 0.0237 (7) | 0.0024 (5) | −0.0043 (5) | −0.0014 (6) |
C1 | 0.0167 (6) | 0.0186 (6) | 0.0129 (6) | 0.0039 (5) | −0.0027 (5) | −0.0013 (5) |
C2 | 0.0205 (7) | 0.0207 (7) | 0.0162 (6) | 0.0001 (5) | −0.0024 (5) | 0.0014 (5) |
C3 | 0.0196 (7) | 0.0202 (7) | 0.0184 (6) | 0.0009 (5) | −0.0043 (5) | −0.0015 (5) |
C4 | 0.0193 (7) | 0.0198 (7) | 0.0137 (6) | 0.0069 (5) | −0.0024 (5) | −0.0001 (5) |
C5 | 0.0209 (7) | 0.0213 (7) | 0.0172 (6) | 0.0013 (6) | 0.0004 (5) | 0.0025 (5) |
C6 | 0.0200 (7) | 0.0203 (7) | 0.0185 (7) | −0.0007 (5) | −0.0022 (5) | −0.0007 (5) |
C7 | 0.0179 (7) | 0.0200 (7) | 0.0158 (6) | 0.0041 (5) | −0.0016 (5) | −0.0012 (5) |
C8 | 0.0221 (7) | 0.0219 (7) | 0.0196 (7) | −0.0006 (6) | −0.0011 (5) | 0.0003 (5) |
C9 | 0.0222 (7) | 0.0201 (7) | 0.0202 (7) | −0.0014 (6) | −0.0045 (6) | −0.0021 (5) |
C10 | 0.0181 (7) | 0.0200 (7) | 0.0158 (6) | 0.0031 (5) | −0.0041 (5) | −0.0037 (5) |
C11 | 0.0187 (7) | 0.0196 (7) | 0.0167 (6) | 0.0001 (5) | −0.0015 (5) | −0.0016 (5) |
C12 | 0.0156 (6) | 0.0176 (6) | 0.0190 (6) | 0.0018 (5) | −0.0020 (5) | −0.0047 (5) |
C13 | 0.0158 (6) | 0.0196 (6) | 0.0150 (6) | −0.0034 (5) | −0.0025 (5) | −0.0011 (5) |
C14 | 0.0207 (7) | 0.0253 (7) | 0.0192 (7) | 0.0051 (6) | −0.0040 (5) | −0.0027 (6) |
C15 | 0.0234 (7) | 0.0254 (7) | 0.0169 (6) | 0.0043 (6) | −0.0022 (6) | −0.0052 (5) |
C16 | 0.0169 (6) | 0.0179 (6) | 0.0163 (6) | −0.0038 (5) | −0.0026 (5) | 0.0005 (5) |
C17 | 0.0191 (7) | 0.0186 (7) | 0.0210 (7) | 0.0021 (5) | −0.0048 (5) | −0.0015 (5) |
C18 | 0.0191 (7) | 0.0196 (7) | 0.0197 (7) | 0.0008 (5) | −0.0029 (5) | −0.0045 (5) |
C19 | 0.0152 (6) | 0.0181 (6) | 0.0157 (6) | −0.0022 (5) | −0.0022 (5) | 0.0004 (5) |
C20 | 0.0173 (7) | 0.0187 (7) | 0.0202 (7) | 0.0015 (5) | −0.0027 (5) | −0.0004 (5) |
C21 | 0.0197 (7) | 0.0204 (7) | 0.0183 (6) | 0.0009 (5) | −0.0016 (5) | −0.0028 (5) |
C22 | 0.0174 (6) | 0.0197 (6) | 0.0151 (6) | −0.0042 (5) | −0.0028 (5) | 0.0010 (5) |
C23 | 0.0205 (7) | 0.0172 (6) | 0.0190 (6) | 0.0020 (5) | −0.0039 (5) | 0.0003 (5) |
C24 | 0.0188 (7) | 0.0162 (6) | 0.0164 (6) | −0.0017 (5) | 0.0002 (5) | −0.0015 (5) |
S1—O2 | 1.4529 (12) | C1—C6 | 1.389 (2) |
S1—O3 | 1.4564 (11) | C1—C2 | 1.396 (2) |
S1—O1 | 1.4624 (10) | C2—C3 | 1.3896 (19) |
S1—C1 | 1.7700 (13) | C2—H1 | 0.9500 |
S2—O8 | 1.4539 (11) | C3—C4 | 1.399 (2) |
S2—O7 | 1.4586 (11) | C3—H2 | 0.9500 |
S2—O6 | 1.4617 (11) | C4—C5 | 1.388 (2) |
S2—C13 | 1.7653 (14) | C5—C6 | 1.3875 (19) |
O4—C10 | 1.3629 (16) | C5—H3 | 0.9500 |
O4—H1H | 0.84 (2) | C6—4H | 0.9500 |
O5—C12 | 1.3383 (17) | C7—C8 | 1.397 (2) |
O5—H2H | 0.98 (3) | C7—C12 | 1.420 (2) |
O9—C22 | 1.3574 (16) | C8—C9 | 1.382 (2) |
O9—H3H | 0.85 (2) | C8—H5 | 0.9500 |
O10—C24 | 1.3413 (16) | C9—C10 | 1.402 (2) |
O10—H4H | 0.93 (3) | C9—H6 | 0.9500 |
O1W—H1W | 0.82 (3) | C10—C11 | 1.385 (2) |
O1W—H2W | 0.84 (3) | C11—C12 | 1.3990 (19) |
O2W—H3W | 0.83 (3) | C11—H8 | 0.9500 |
O2W—H4W | 0.867 (10) | C13—C14 | 1.3913 (19) |
O3W—H5W | 0.88 (3) | C13—C18 | 1.3940 (19) |
O3W—H6W | 0.95 (3) | C14—C15 | 1.3863 (19) |
O4W—H7W | 0.81 (2) | C14—H10 | 0.9500 |
O4W—H8W | 0.81 (3) | C15—C16 | 1.391 (2) |
N1—N2 | 1.2680 (17) | C15—H11 | 0.9500 |
N1—C4 | 1.4227 (17) | C16—C17 | 1.3943 (19) |
N2—C7 | 1.4050 (17) | C17—C18 | 1.3874 (19) |
N3—N4 | 1.2756 (16) | C17—H12 | 0.9500 |
N3—C16 | 1.4244 (17) | C18—H13 | 0.9500 |
N4—C19 | 1.3963 (17) | C19—C20 | 1.4041 (19) |
N5—H1N | 0.80 (2) | C19—C24 | 1.4221 (19) |
N5—H2N | 0.92 (2) | C20—C21 | 1.3799 (19) |
N5—H3N | 0.94 (2) | C20—H14 | 0.9500 |
N5—H4N | 0.89 (2) | C21—C22 | 1.4059 (19) |
N6—H5N | 0.90 (2) | C21—H15 | 0.9500 |
N6—H6N | 0.92 (2) | C22—C23 | 1.3874 (19) |
N6—H7N | 0.92 (2) | C23—C24 | 1.3919 (19) |
N6—H8N | 0.84 (2) | C23—H17 | 0.9500 |
O2—S1—O3 | 113.29 (7) | C8—C7—N2 | 115.77 (13) |
O2—S1—O1 | 111.57 (6) | C8—C7—C12 | 119.15 (13) |
O3—S1—O1 | 111.92 (7) | N2—C7—C12 | 125.08 (13) |
O2—S1—C1 | 106.74 (7) | C9—C8—C7 | 121.46 (14) |
O3—S1—C1 | 106.36 (6) | C9—C8—H5 | 119.3 |
O1—S1—C1 | 106.44 (6) | C7—C8—H5 | 119.3 |
O8—S2—O7 | 112.77 (7) | C8—C9—C10 | 118.78 (14) |
O8—S2—O6 | 112.41 (7) | C8—C9—H6 | 120.6 |
O7—S2—O6 | 110.95 (7) | C10—C9—H6 | 120.6 |
O8—S2—C13 | 106.48 (6) | O4—C10—C11 | 121.49 (13) |
O7—S2—C13 | 106.47 (6) | O4—C10—C9 | 117.21 (13) |
O6—S2—C13 | 107.32 (6) | C11—C10—C9 | 121.31 (13) |
C10—O4—H1H | 110.2 (15) | C10—C11—C12 | 119.88 (13) |
C12—O5—H2H | 101.5 (15) | C10—C11—H8 | 120.1 |
C22—O9—H3H | 110.6 (15) | C12—C11—H8 | 120.1 |
C24—O10—H4H | 103.8 (15) | O5—C12—C11 | 118.27 (13) |
H1W—O1W—H2W | 109 (2) | O5—C12—C7 | 122.31 (12) |
H3W—O2W—H4W | 105 (2) | C11—C12—C7 | 119.42 (13) |
H5W—O3W—H6W | 104 (2) | C14—C13—C18 | 120.74 (13) |
H7W—O4W—H8W | 104 (2) | C14—C13—S2 | 120.09 (11) |
N2—N1—C4 | 114.84 (12) | C18—C13—S2 | 119.11 (10) |
N1—N2—C7 | 114.40 (12) | C15—C14—C13 | 119.86 (13) |
N4—N3—C16 | 114.71 (11) | C15—C14—H10 | 120.1 |
N3—N4—C19 | 114.81 (11) | C13—C14—H10 | 120.1 |
H1N—N5—H2N | 111.0 (18) | C14—C15—C16 | 119.56 (13) |
H1N—N5—H3N | 113.3 (19) | C14—C15—H11 | 120.2 |
H2N—N5—H3N | 108.3 (19) | C16—C15—H11 | 120.2 |
H1N—N5—H4N | 108.0 (19) | C15—C16—C17 | 120.60 (13) |
H2N—N5—H4N | 107.7 (19) | C15—C16—N3 | 123.87 (12) |
H3N—N5—H4N | 108.4 (19) | C17—C16—N3 | 115.52 (12) |
H5N—N6—H6N | 110.5 (18) | C18—C17—C16 | 119.88 (13) |
H5N—N6—H7N | 110.3 (19) | C18—C17—H12 | 120.1 |
H6N—N6—H7N | 107.0 (18) | C16—C17—H12 | 120.1 |
H5N—N6—H8N | 109 (2) | C17—C18—C13 | 119.34 (13) |
H6N—N6—H8N | 112 (2) | C17—C18—H13 | 120.3 |
H7N—N6—H8N | 108 (2) | C13—C18—H13 | 120.3 |
C6—C1—C2 | 120.97 (12) | N4—C19—C20 | 116.23 (12) |
C6—C1—S1 | 119.83 (11) | N4—C19—C24 | 125.04 (12) |
C2—C1—S1 | 119.18 (11) | C20—C19—C24 | 118.73 (12) |
C3—C2—C1 | 119.78 (13) | C21—C20—C19 | 121.30 (13) |
C3—C2—H1 | 120.1 | C21—C20—H14 | 119.3 |
C1—C2—H1 | 120.1 | C19—C20—H14 | 119.3 |
C2—C3—C4 | 119.12 (13) | C20—C21—C22 | 119.15 (13) |
C2—C3—H2 | 120.4 | C20—C21—H15 | 120.4 |
C4—C3—H2 | 120.4 | C22—C21—H15 | 120.4 |
C5—C4—C3 | 120.73 (13) | O9—C22—C23 | 117.27 (12) |
C5—C4—N1 | 114.64 (13) | O9—C22—C21 | 121.83 (12) |
C3—C4—N1 | 124.62 (13) | C23—C22—C21 | 120.89 (12) |
C6—C5—C4 | 120.20 (13) | C22—C23—C24 | 120.02 (13) |
C6—C5—H3 | 119.9 | C22—C23—H17 | 120.0 |
C4—C5—H3 | 119.9 | C24—C23—H17 | 120.0 |
C5—C6—C1 | 119.19 (13) | O10—C24—C23 | 118.42 (12) |
C5—C6—4H | 120.4 | O10—C24—C19 | 121.70 (12) |
C1—C6—4H | 120.4 | C23—C24—C19 | 119.87 (12) |
C4—N1—N2—C7 | −179.73 (11) | N2—C7—C12—C11 | −179.40 (12) |
C16—N3—N4—C19 | −179.87 (11) | O8—S2—C13—C14 | −14.43 (14) |
O2—S1—C1—C6 | 12.29 (13) | O7—S2—C13—C14 | 106.13 (13) |
O3—S1—C1—C6 | 133.52 (11) | O6—S2—C13—C14 | −135.01 (12) |
O1—S1—C1—C6 | −106.99 (12) | O8—S2—C13—C18 | 168.28 (12) |
O2—S1—C1—C2 | −169.23 (11) | O7—S2—C13—C18 | −71.16 (13) |
O3—S1—C1—C2 | −47.99 (13) | O6—S2—C13—C18 | 47.70 (13) |
O1—S1—C1—C2 | 71.50 (12) | C18—C13—C14—C15 | 0.6 (2) |
C6—C1—C2—C3 | −0.3 (2) | S2—C13—C14—C15 | −176.62 (12) |
S1—C1—C2—C3 | −178.79 (10) | C13—C14—C15—C16 | −0.4 (2) |
C1—C2—C3—C4 | −0.3 (2) | C14—C15—C16—C17 | −0.7 (2) |
C2—C3—C4—C5 | 0.5 (2) | C14—C15—C16—N3 | 178.73 (14) |
C2—C3—C4—N1 | 179.66 (12) | N4—N3—C16—C15 | −7.1 (2) |
N2—N1—C4—C5 | −178.08 (12) | N4—N3—C16—C17 | 172.30 (13) |
N2—N1—C4—C3 | 2.70 (19) | C15—C16—C17—C18 | 1.5 (2) |
C3—C4—C5—C6 | 0.0 (2) | N3—C16—C17—C18 | −178.00 (13) |
N1—C4—C5—C6 | −179.29 (12) | C16—C17—C18—C13 | −1.2 (2) |
C4—C5—C6—C1 | −0.6 (2) | C14—C13—C18—C17 | 0.1 (2) |
C2—C1—C6—C5 | 0.8 (2) | S2—C13—C18—C17 | 177.42 (11) |
S1—C1—C6—C5 | 179.23 (11) | N3—N4—C19—C20 | 178.63 (12) |
N1—N2—C7—C8 | 179.98 (12) | N3—N4—C19—C24 | −0.9 (2) |
N1—N2—C7—C12 | 0.06 (19) | N4—C19—C20—C21 | 179.16 (13) |
N2—C7—C8—C9 | 179.75 (13) | C24—C19—C20—C21 | −1.2 (2) |
C12—C7—C8—C9 | −0.3 (2) | C19—C20—C21—C22 | 1.7 (2) |
C7—C8—C9—C10 | −0.4 (2) | C20—C21—C22—O9 | 178.72 (13) |
C8—C9—C10—O4 | −179.37 (13) | C20—C21—C22—C23 | −0.4 (2) |
C8—C9—C10—C11 | 0.7 (2) | O9—C22—C23—C24 | 179.45 (13) |
O4—C10—C11—C12 | 179.74 (12) | C21—C22—C23—C24 | −1.4 (2) |
C9—C10—C11—C12 | −0.4 (2) | C22—C23—C24—O10 | −177.09 (13) |
C10—C11—C12—O5 | 179.41 (12) | C22—C23—C24—C19 | 1.9 (2) |
C10—C11—C12—C7 | −0.3 (2) | N4—C19—C24—O10 | −2.1 (2) |
C8—C7—C12—O5 | −179.05 (13) | C20—C19—C24—O10 | 178.33 (13) |
N2—C7—C12—O5 | 0.9 (2) | N4—C19—C24—C23 | 178.99 (13) |
C8—C7—C12—C11 | 0.7 (2) | C20—C19—C24—C23 | −0.6 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H1H···O4W | 0.84 (2) | 1.81 (2) | 2.6357 (17) | 170 (2) |
O5—H2H···N1 | 0.98 (3) | 1.65 (3) | 2.5535 (16) | 151 (2) |
O9—H3H···O2W | 0.85 (2) | 1.83 (2) | 2.6673 (16) | 168 (2) |
O10—H4H···N3 | 0.93 (3) | 1.69 (3) | 2.5420 (16) | 149 (2) |
N5—H1N···O1i | 0.80 (2) | 2.16 (2) | 2.8858 (17) | 151.1 (18) |
N5—H1N···O1Wii | 0.80 (2) | 2.627 (19) | 3.034 (2) | 113.3 (15) |
N5—H2N···O1 | 0.92 (2) | 1.94 (2) | 2.8403 (18) | 168 (2) |
N5—H3N···O3Wiii | 0.94 (2) | 1.91 (2) | 2.8488 (17) | 172 (2) |
N5—H4N···O6iv | 0.89 (2) | 2.01 (2) | 2.8425 (16) | 156 (2) |
N6—H5N···S2v | 0.90 (2) | 2.99 (2) | 3.7547 (15) | 143.5 (17) |
N6—H5N···O7v | 0.90 (2) | 1.99 (2) | 2.8804 (18) | 168 (2) |
N6—H6N···O1W | 0.92 (2) | 1.90 (2) | 2.8027 (18) | 169.7 (19) |
N6—H7N···O3Wvi | 0.92 (2) | 1.96 (2) | 2.8733 (19) | 170.4 (19) |
N6—H8N···O2vii | 0.84 (2) | 2.42 (2) | 2.9090 (18) | 117.8 (18) |
N6—H8N···O3v | 0.84 (2) | 2.36 (2) | 2.9153 (17) | 123.8 (19) |
O1W—H2W···O4viii | 0.84 (3) | 2.01 (3) | 2.8150 (16) | 162 (2) |
O1W—H1W···O8 | 0.82 (3) | 1.98 (3) | 2.7858 (17) | 166 (2) |
O2W—H3W···O3viii | 0.83 (3) | 2.04 (3) | 2.8639 (16) | 171 (2) |
O2W—H4W···O8vi | 0.87 (1) | 1.94 (1) | 2.7918 (17) | 169 (2) |
O3W—H5W···O7viii | 0.88 (3) | 1.83 (3) | 2.7106 (16) | 179 (2) |
O3W—H6W···O9 | 0.95 (3) | 2.04 (3) | 2.8347 (15) | 140 (2) |
O4W—H7W···O2ix | 0.81 (2) | 1.94 (2) | 2.7482 (17) | 175 (2) |
O4W—H8W···O6ix | 0.81 (3) | 2.01 (3) | 2.8128 (16) | 171 (2) |
Symmetry codes: (i) −x+2, −y, −z; (ii) −x+1, −y+1, −z; (iii) x, y, z−1; (iv) x+1, y, z; (v) −x, −y+1, −z; (vi) −x, −y+1, −z+1; (vii) x−1, y+1, z; (viii) −x+1, −y+1, −z+1; (ix) −x+1, −y, −z+1. |
NH4+·C12H10N3O3S−·1.5(H2O) | F(000) = 1352 |
Mr = 321.35 | Dx = 1.489 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.7107 Å |
a = 35.1636 (15) Å | Cell parameters from 3419 reflections |
b = 7.8905 (3) Å | θ = 1.0–27.5° |
c = 10.4972 (5) Å | µ = 0.25 mm−1 |
β = 100.091 (2)° | T = 123 K |
V = 2867.5 (2) Å3 | Plate, yellow |
Z = 8 | 0.35 × 0.30 × 0.05 mm |
Enraf–Nonius KappaCCD diffractometer | Rint = 0.074 |
Radiation source: sealed tube | θmax = 27.5°, θmin = 2.4° |
phi and ω scans | h = −45→45 |
6133 measured reflections | k = −10→10 |
3271 independent reflections | l = −13→13 |
1857 reflections with I > 2σ(I) |
Refinement on F2 | 1 restraint |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.049 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.105 | w = 1/[σ2(Fo2) + (0.0404P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
3271 reflections | Δρmax = 0.26 e Å−3 |
231 parameters | Δρmin = −0.46 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.43663 (2) | 0.11499 (8) | 0.70251 (6) | 0.01953 (19) | |
O1 | 0.45304 (4) | 0.2492 (2) | 0.79049 (15) | 0.0232 (4) | |
O2 | 0.45060 (5) | −0.0525 (2) | 0.74823 (16) | 0.0254 (4) | |
O3 | 0.44203 (5) | 0.1429 (2) | 0.56905 (15) | 0.0258 (4) | |
O1W | 0.43599 (5) | 0.5179 (3) | 0.9712 (2) | 0.0288 (5) | |
O2W | 0.000000 | 0.0222 (3) | 0.750000 | 0.0255 (6) | |
N1 | 0.26669 (5) | 0.1179 (2) | 0.69356 (18) | 0.0206 (5) | |
N2 | 0.25653 (6) | 0.1029 (2) | 0.80233 (19) | 0.0209 (5) | |
N3 | 0.09692 (6) | 0.1286 (3) | 0.8002 (2) | 0.0229 (5) | |
N4 | 0.01011 (8) | 0.2779 (3) | 0.9447 (2) | 0.0231 (5) | |
C1 | 0.38640 (6) | 0.1194 (3) | 0.7015 (2) | 0.0158 (5) | |
C2 | 0.37175 (7) | 0.1937 (3) | 0.8030 (2) | 0.0178 (6) | |
H3 | 0.388827 | 0.245602 | 0.872118 | 0.021* | |
C3 | 0.33251 (7) | 0.1922 (3) | 0.8037 (2) | 0.0199 (6) | |
H4 | 0.322609 | 0.241477 | 0.873737 | 0.024* | |
C4 | 0.30749 (7) | 0.1180 (3) | 0.7009 (2) | 0.0182 (6) | |
C5 | 0.32184 (7) | 0.0481 (3) | 0.5976 (2) | 0.0193 (6) | |
H1 | 0.304641 | 0.001030 | 0.526474 | 0.023* | |
C6 | 0.36131 (7) | 0.0470 (3) | 0.5983 (2) | 0.0189 (6) | |
H2 | 0.371235 | −0.002996 | 0.528569 | 0.023* | |
C7 | 0.21591 (7) | 0.1143 (3) | 0.7977 (2) | 0.0189 (6) | |
C8 | 0.20127 (7) | 0.0432 (3) | 0.9007 (2) | 0.0217 (6) | |
H7 | 0.218270 | −0.007777 | 0.970567 | 0.026* | |
C9 | 0.16185 (7) | 0.0469 (3) | 0.9011 (2) | 0.0204 (6) | |
H8 | 0.151853 | −0.005480 | 0.969770 | 0.024* | |
C10 | 0.13691 (7) | 0.1264 (3) | 0.8022 (2) | 0.0177 (6) | |
C11 | 0.15198 (7) | 0.2021 (3) | 0.7018 (2) | 0.0211 (6) | |
H6 | 0.135167 | 0.259073 | 0.634717 | 0.025* | |
C12 | 0.19107 (7) | 0.1952 (3) | 0.6988 (2) | 0.0197 (6) | |
H5 | 0.200951 | 0.245721 | 0.629153 | 0.024* | |
H1N | 0.0074 (8) | 0.178 (4) | 0.902 (3) | 0.046 (9)* | |
H2N | 0.0243 (9) | 0.255 (4) | 1.028 (3) | 0.068 (11)* | |
H3N | 0.0210 (9) | 0.348 (4) | 0.900 (3) | 0.065 (12)* | |
H4N | −0.0141 (10) | 0.327 (4) | 0.963 (3) | 0.081 (12)* | |
H5N | 0.0911 (8) | 0.092 (3) | 0.870 (3) | 0.036 (9)* | |
H6N | 0.0856 (7) | 0.223 (4) | 0.775 (2) | 0.038 (9)* | |
H1W | 0.4271 (8) | 0.525 (4) | 0.892 (3) | 0.040 (10)* | |
H2W | 0.4346 (9) | 0.622 (4) | 1.000 (3) | 0.065 (12)* | |
H3W | −0.0192 (6) | −0.044 (3) | 0.757 (3) | 0.049 (10)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0178 (3) | 0.0194 (3) | 0.0217 (4) | −0.0012 (3) | 0.0044 (3) | −0.0010 (3) |
O1 | 0.0187 (10) | 0.0243 (10) | 0.0269 (10) | −0.0035 (8) | 0.0046 (7) | −0.0055 (9) |
O2 | 0.0190 (10) | 0.0197 (10) | 0.0370 (11) | 0.0025 (8) | 0.0038 (8) | 0.0025 (8) |
O3 | 0.0229 (10) | 0.0360 (12) | 0.0202 (9) | −0.0035 (9) | 0.0087 (7) | 0.0004 (8) |
O1W | 0.0314 (12) | 0.0306 (13) | 0.0240 (13) | 0.0036 (10) | 0.0038 (9) | 0.0001 (10) |
O2W | 0.0249 (17) | 0.0245 (16) | 0.0294 (15) | 0.000 | 0.0109 (13) | 0.000 |
N1 | 0.0201 (12) | 0.0199 (12) | 0.0226 (12) | −0.0003 (10) | 0.0058 (9) | −0.0003 (11) |
N2 | 0.0186 (12) | 0.0218 (12) | 0.0234 (12) | −0.0003 (10) | 0.0066 (9) | 0.0005 (10) |
N3 | 0.0201 (13) | 0.0218 (14) | 0.0276 (14) | 0.0016 (12) | 0.0064 (10) | 0.0020 (12) |
N4 | 0.0245 (14) | 0.0216 (15) | 0.0237 (15) | −0.0005 (12) | 0.0058 (12) | −0.0015 (13) |
C1 | 0.0166 (13) | 0.0121 (13) | 0.0188 (13) | 0.0001 (12) | 0.0039 (10) | 0.0060 (12) |
C2 | 0.0186 (14) | 0.0163 (13) | 0.0178 (13) | −0.0021 (12) | 0.0011 (10) | 0.0012 (11) |
C3 | 0.0213 (14) | 0.0211 (14) | 0.0186 (13) | −0.0011 (12) | 0.0068 (11) | −0.0005 (12) |
C4 | 0.0158 (13) | 0.0173 (13) | 0.0215 (14) | 0.0019 (12) | 0.0037 (10) | 0.0048 (12) |
C5 | 0.0225 (15) | 0.0195 (14) | 0.0140 (13) | −0.0016 (12) | −0.0022 (11) | 0.0027 (11) |
C6 | 0.0199 (14) | 0.0205 (14) | 0.0173 (14) | 0.0022 (12) | 0.0064 (11) | −0.0002 (12) |
C7 | 0.0168 (14) | 0.0176 (13) | 0.0219 (14) | 0.0007 (12) | 0.0023 (11) | −0.0041 (12) |
C8 | 0.0214 (15) | 0.0242 (14) | 0.0184 (14) | 0.0013 (12) | 0.0008 (11) | 0.0004 (12) |
C9 | 0.0246 (15) | 0.0199 (14) | 0.0184 (14) | −0.0031 (12) | 0.0085 (11) | −0.0006 (12) |
C10 | 0.0185 (14) | 0.0141 (13) | 0.0214 (14) | 0.0002 (12) | 0.0057 (11) | −0.0016 (12) |
C11 | 0.0217 (14) | 0.0199 (14) | 0.0204 (14) | 0.0044 (12) | 0.0004 (11) | −0.0009 (12) |
C12 | 0.0204 (14) | 0.0197 (14) | 0.0195 (14) | −0.0026 (12) | 0.0043 (11) | −0.0001 (12) |
S1—O1 | 1.4564 (17) | C1—C6 | 1.394 (3) |
S1—O2 | 1.4612 (17) | C2—C3 | 1.381 (3) |
S1—O3 | 1.4630 (16) | C2—H3 | 0.9500 |
S1—C1 | 1.765 (2) | C3—C4 | 1.396 (3) |
O1W—H1W | 0.83 (3) | C3—H4 | 0.9500 |
O1W—H2W | 0.88 (3) | C4—C5 | 1.389 (3) |
O2W—H3W | 0.867 (10) | C5—C6 | 1.387 (3) |
O2W—H3Wi | 0.867 (10) | C5—H1 | 0.9500 |
N1—N2 | 1.260 (2) | C6—H2 | 0.9500 |
N1—C4 | 1.423 (3) | C7—C12 | 1.390 (3) |
N2—C7 | 1.423 (3) | C7—C8 | 1.394 (3) |
N3—C10 | 1.403 (3) | C8—C9 | 1.387 (3) |
N3—H5N | 0.85 (3) | C8—H7 | 0.9500 |
N3—H6N | 0.86 (3) | C9—C10 | 1.387 (3) |
N4—H1N | 0.90 (3) | C9—H8 | 0.9500 |
N4—H2N | 0.94 (3) | C10—C11 | 1.394 (3) |
N4—H3N | 0.86 (3) | C11—C12 | 1.382 (3) |
N4—H4N | 0.98 (4) | C11—H6 | 0.9500 |
C1—C2 | 1.391 (3) | C12—H5 | 0.9500 |
O1—S1—O2 | 112.10 (10) | C5—C4—C3 | 120.3 (2) |
O1—S1—O3 | 113.23 (10) | C5—C4—N1 | 117.3 (2) |
O2—S1—O3 | 110.97 (10) | C3—C4—N1 | 122.4 (2) |
O1—S1—C1 | 105.93 (10) | C6—C5—C4 | 119.9 (2) |
O2—S1—C1 | 107.36 (10) | C6—C5—H1 | 120.0 |
O3—S1—C1 | 106.79 (10) | C4—C5—H1 | 120.0 |
H1W—O1W—H2W | 104 (3) | C5—C6—C1 | 119.9 (2) |
H3W—O2W—H3Wi | 106 (4) | C5—C6—H2 | 120.1 |
N2—N1—C4 | 113.20 (18) | C1—C6—H2 | 120.1 |
N1—N2—C7 | 113.92 (19) | C12—C7—C8 | 119.7 (2) |
C10—N3—H5N | 112.2 (18) | C12—C7—N2 | 123.3 (2) |
C10—N3—H6N | 114.9 (18) | C8—C7—N2 | 116.9 (2) |
H5N—N3—H6N | 113 (3) | C9—C8—C7 | 119.9 (2) |
H1N—N4—H2N | 106 (3) | C9—C8—H7 | 120.0 |
H1N—N4—H3N | 108 (3) | C7—C8—H7 | 120.0 |
H2N—N4—H3N | 115 (3) | C10—C9—C8 | 120.6 (2) |
H1N—N4—H4N | 115 (3) | C10—C9—H8 | 119.7 |
H2N—N4—H4N | 103 (2) | C8—C9—H8 | 119.7 |
H3N—N4—H4N | 110 (3) | C9—C10—C11 | 119.0 (2) |
C2—C1—C6 | 119.9 (2) | C9—C10—N3 | 121.1 (2) |
C2—C1—S1 | 120.53 (17) | C11—C10—N3 | 119.8 (2) |
C6—C1—S1 | 119.54 (18) | C12—C11—C10 | 120.8 (2) |
C3—C2—C1 | 120.3 (2) | C12—C11—H6 | 119.6 |
C3—C2—H3 | 119.8 | C10—C11—H6 | 119.6 |
C1—C2—H3 | 119.8 | C11—C12—C7 | 119.9 (2) |
C2—C3—C4 | 119.6 (2) | C11—C12—H5 | 120.1 |
C2—C3—H4 | 120.2 | C7—C12—H5 | 120.1 |
C4—C3—H4 | 120.2 | ||
C4—N1—N2—C7 | 175.90 (19) | C4—C5—C6—C1 | −1.4 (4) |
O1—S1—C1—C2 | −21.1 (2) | C2—C1—C6—C5 | −0.5 (3) |
O2—S1—C1—C2 | 98.82 (19) | S1—C1—C6—C5 | 179.20 (18) |
O3—S1—C1—C2 | −142.10 (19) | N1—N2—C7—C12 | −23.1 (3) |
O1—S1—C1—C6 | 159.19 (18) | N1—N2—C7—C8 | 158.6 (2) |
O2—S1—C1—C6 | −80.9 (2) | C12—C7—C8—C9 | 2.9 (4) |
O3—S1—C1—C6 | 38.2 (2) | N2—C7—C8—C9 | −178.7 (2) |
C6—C1—C2—C3 | 1.7 (3) | C7—C8—C9—C10 | −2.4 (4) |
S1—C1—C2—C3 | −178.02 (18) | C8—C9—C10—C11 | 0.3 (4) |
C1—C2—C3—C4 | −1.0 (4) | C8—C9—C10—N3 | 178.9 (2) |
C2—C3—C4—C5 | −0.9 (4) | C9—C10—C11—C12 | 1.4 (3) |
C2—C3—C4—N1 | −177.6 (2) | N3—C10—C11—C12 | −177.2 (2) |
N2—N1—C4—C5 | 147.6 (2) | C10—C11—C12—C7 | −1.0 (3) |
N2—N1—C4—C3 | −35.6 (3) | C8—C7—C12—C11 | −1.2 (3) |
C3—C4—C5—C6 | 2.1 (4) | N2—C7—C12—C11 | −179.5 (2) |
N1—C4—C5—C6 | 179.0 (2) |
Symmetry code: (i) −x, y, −z+3/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H1N···O2W | 0.90 (3) | 2.00 (3) | 2.850 (3) | 157 (2) |
N4—H2N···O1ii | 0.94 (3) | 1.93 (3) | 2.862 (3) | 167 (3) |
N4—H2N···O1Wii | 0.94 (3) | 2.57 (3) | 3.039 (3) | 111 (2) |
N4—H3N···O2iii | 0.86 (3) | 2.14 (3) | 2.963 (3) | 161 (3) |
N4—H3N···O3iii | 0.86 (3) | 2.66 (3) | 3.351 (3) | 139 (3) |
N4—H4N···O3iv | 0.98 (4) | 2.07 (4) | 2.987 (3) | 155 (3) |
N3—H5N···O1Wii | 0.85 (3) | 2.23 (3) | 3.067 (3) | 168 (2) |
N3—H6N···O2iii | 0.86 (3) | 2.17 (3) | 3.015 (3) | 165 (2) |
O1W—H1W···N3iii | 0.83 (3) | 2.21 (3) | 3.011 (3) | 162 (3) |
O1W—H2W···O3v | 0.88 (3) | 1.99 (3) | 2.861 (3) | 169 (3) |
O2W—H3W···O1vi | 0.87 (1) | 1.97 (1) | 2.792 (3) | 159 (3) |
Symmetry codes: (ii) −x+1/2, −y+1/2, −z+2; (iii) −x+1/2, y+1/2, −z+3/2; (iv) x−1/2, −y+1/2, z+1/2; (v) x, −y+1, z+1/2; (vi) x−1/2, y−1/2, z. |
NH4+·C16H18N3O5S−·H2O | Z = 4 |
Mr = 400.45 | F(000) = 848 |
Triclinic, P1 | Dx = 1.437 Mg m−3 |
a = 8.4933 (1) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 13.0977 (2) Å | Cell parameters from 8751 reflections |
c = 17.1657 (3) Å | θ = 1.0–27.9° |
α = 90.970 (1)° | µ = 0.22 mm−1 |
β = 103.180 (1)° | T = 123 K |
γ = 95.132 (1)° | Cut plate, yellow orange |
V = 1850.43 (5) Å3 | 0.5 × 0.5 × 0.15 mm |
Enraf–Nonius KappaCCD diffractometer | Rint = 0.043 |
Radiation source: sealed tube | θmax = 28.0°, θmin = 1.2° |
phi and ω scans | h = −11→11 |
16736 measured reflections | k = −17→17 |
8841 independent reflections | l = −22→22 |
5911 reflections with I > 2σ(I) |
Refinement on F2 | 8 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.047 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.118 | w = 1/[σ2(Fo2) + (0.0528P)2 + 0.4114P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
8841 reflections | Δρmax = 0.57 e Å−3 |
550 parameters | Δρmin = −0.42 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
S1 | −0.17962 (6) | 0.40832 (4) | 0.11851 (3) | 0.02084 (13) | |
S1A | 0.89947 (6) | 0.10864 (4) | 0.81730 (3) | 0.02110 (13) | |
O1 | −0.35205 (17) | 0.38875 (12) | 0.11656 (9) | 0.0329 (4) | |
O1A | 0.88697 (18) | −0.00026 (10) | 0.79522 (9) | 0.0297 (4) | |
O2 | −0.12780 (18) | 0.51596 (10) | 0.11604 (9) | 0.0303 (4) | |
O2A | 0.7922 (2) | 0.13162 (13) | 0.86831 (9) | 0.0399 (4) | |
O3 | −0.13347 (18) | 0.34429 (11) | 0.05857 (8) | 0.0275 (3) | |
O3A | 1.06745 (17) | 0.14814 (11) | 0.85103 (9) | 0.0270 (3) | |
O4 | 0.3424 (2) | 0.03149 (12) | 0.90342 (9) | 0.0310 (4) | |
O4A | 0.3842 (2) | 0.50130 (13) | 0.07514 (9) | 0.0298 (4) | |
O5 | 0.6302 (2) | −0.14218 (13) | 0.77988 (9) | 0.0299 (4) | |
O5A | 0.5451 (2) | 0.69228 (13) | 0.07851 (9) | 0.0338 (4) | |
N1 | 0.0781 (2) | 0.23905 (13) | 0.43773 (10) | 0.0220 (4) | |
N1A | 0.6312 (2) | 0.32623 (13) | 0.52115 (10) | 0.0239 (4) | |
N2 | 0.1444 (2) | 0.15696 (13) | 0.43423 (10) | 0.0236 (4) | |
N2A | 0.7053 (2) | 0.41022 (13) | 0.50930 (10) | 0.0230 (4) | |
N3 | 0.3017 (2) | −0.08822 (12) | 0.69994 (10) | 0.0213 (4) | |
N3A | 0.4234 (2) | 0.61579 (12) | 0.23547 (10) | 0.0204 (4) | |
N4 | 0.1309 (3) | 0.30779 (17) | −0.02165 (13) | 0.0305 (5) | |
N5 | 0.6587 (3) | 0.15278 (17) | 1.00084 (13) | 0.0289 (4) | |
C1 | −0.0800 (2) | 0.36624 (14) | 0.21287 (12) | 0.0187 (4) | |
C1A | 0.8318 (2) | 0.17296 (15) | 0.72803 (12) | 0.0200 (4) | |
C2 | −0.0972 (3) | 0.41491 (15) | 0.28276 (12) | 0.0228 (5) | |
H2 | −0.149957 | 0.476152 | 0.279943 | 0.027* | |
C2A | 0.6835 (3) | 0.13752 (15) | 0.67789 (12) | 0.0227 (5) | |
H2A | 0.624361 | 0.077229 | 0.690080 | 0.027* | |
C3 | −0.0375 (2) | 0.37424 (15) | 0.35638 (12) | 0.0222 (5) | |
H3 | −0.047185 | 0.408354 | 0.404098 | 0.027* | |
C3A | 0.6224 (3) | 0.19002 (15) | 0.61039 (12) | 0.0235 (5) | |
H3A | 0.520852 | 0.165819 | 0.576214 | 0.028* | |
C4 | 0.0369 (2) | 0.28326 (15) | 0.36042 (12) | 0.0198 (4) | |
C4A | 0.7085 (3) | 0.27817 (15) | 0.59206 (12) | 0.0219 (5) | |
C5 | 0.0585 (2) | 0.23671 (15) | 0.29092 (12) | 0.0214 (4) | |
H5 | 0.112535 | 0.175969 | 0.293915 | 0.026* | |
C5A | 0.8571 (3) | 0.31410 (16) | 0.64225 (13) | 0.0248 (5) | |
H5A | 0.915888 | 0.374439 | 0.629883 | 0.030* | |
C6 | 0.0020 (2) | 0.27789 (15) | 0.21743 (12) | 0.0220 (4) | |
H6 | 0.018872 | 0.246300 | 0.170152 | 0.026* | |
C6A | 0.9192 (3) | 0.26163 (15) | 0.71037 (12) | 0.0239 (5) | |
H6A | 1.020451 | 0.285888 | 0.744758 | 0.029* | |
C7 | 0.1810 (2) | 0.10273 (15) | 0.50505 (12) | 0.0223 (5) | |
C7A | 0.6255 (3) | 0.45964 (15) | 0.44071 (12) | 0.0215 (4) | |
C8 | 0.2579 (3) | 0.01469 (16) | 0.49867 (13) | 0.0253 (5) | |
H8 | 0.281847 | −0.002980 | 0.448998 | 0.030* | |
C8A | 0.7089 (3) | 0.54725 (15) | 0.41917 (12) | 0.0226 (5) | |
H8A | 0.811905 | 0.572131 | 0.451636 | 0.027* | |
C9 | 0.3005 (3) | −0.04780 (16) | 0.56259 (12) | 0.0245 (5) | |
H9 | 0.355253 | −0.106573 | 0.556626 | 0.029* | |
C9A | 0.6442 (2) | 0.59843 (15) | 0.35140 (12) | 0.0217 (4) | |
H9A | 0.704469 | 0.657026 | 0.337306 | 0.026* | |
C10 | 0.2635 (2) | −0.02522 (15) | 0.63652 (12) | 0.0205 (4) | |
C10A | 0.4899 (2) | 0.56516 (14) | 0.30270 (12) | 0.0195 (4) | |
C11 | 0.1840 (2) | 0.06468 (15) | 0.64191 (12) | 0.0231 (5) | |
H11 | 0.158480 | 0.082624 | 0.691148 | 0.028* | |
C11A | 0.4039 (3) | 0.47813 (15) | 0.32746 (12) | 0.0221 (4) | |
H11A | 0.298707 | 0.454379 | 0.296832 | 0.026* | |
C12 | 0.1430 (2) | 0.12635 (15) | 0.57798 (12) | 0.0225 (5) | |
H12 | 0.088398 | 0.185410 | 0.583295 | 0.027* | |
C12A | 0.4703 (3) | 0.42788 (15) | 0.39475 (12) | 0.0233 (5) | |
H12A | 0.409623 | 0.370507 | 0.410364 | 0.028* | |
C13 | 0.2643 (3) | −0.06521 (16) | 0.77689 (12) | 0.0240 (5) | |
H13A | 0.258991 | −0.129575 | 0.805996 | 0.029* | |
H13B | 0.155624 | −0.039534 | 0.766994 | 0.029* | |
C13A | 0.2716 (3) | 0.57465 (16) | 0.18036 (12) | 0.0241 (5) | |
H13C | 0.231958 | 0.628891 | 0.143451 | 0.029* | |
H13D | 0.189095 | 0.557588 | 0.211785 | 0.029* | |
C14 | 0.3863 (3) | 0.01328 (16) | 0.82977 (12) | 0.0257 (5) | |
H14A | 0.495397 | −0.011879 | 0.840483 | 0.031* | |
H14B | 0.391470 | 0.078372 | 0.801570 | 0.031* | |
C14A | 0.2853 (3) | 0.48032 (17) | 0.13115 (13) | 0.0300 (5) | |
H14C | 0.332100 | 0.427377 | 0.167557 | 0.036* | |
H14D | 0.175268 | 0.452262 | 0.101761 | 0.036* | |
C15 | 0.3707 (3) | −0.18485 (15) | 0.69021 (13) | 0.0237 (5) | |
H15A | 0.318931 | −0.215719 | 0.636409 | 0.028* | |
H15B | 0.343701 | −0.232829 | 0.730219 | 0.028* | |
C15A | 0.5049 (3) | 0.71091 (15) | 0.21544 (12) | 0.0232 (5) | |
H15C | 0.565540 | 0.747437 | 0.265797 | 0.028* | |
H15D | 0.421297 | 0.754838 | 0.188657 | 0.028* | |
C16 | 0.5525 (3) | −0.17382 (16) | 0.69951 (13) | 0.0262 (5) | |
H16A | 0.588976 | −0.240219 | 0.686007 | 0.031* | |
H16B | 0.582318 | −0.122439 | 0.662418 | 0.031* | |
C16A | 0.6218 (3) | 0.69837 (17) | 0.16185 (13) | 0.0277 (5) | |
H16C | 0.706454 | 0.757198 | 0.172350 | 0.033* | |
H16D | 0.676385 | 0.635262 | 0.175844 | 0.033* | |
O1W | 0.3971 (2) | 0.22906 (13) | 0.08102 (10) | 0.0413 (4) | |
H1W | 0.473 (2) | 0.2803 (14) | 0.0933 (14) | 0.050* | |
H2W | 0.393 (3) | 0.2095 (18) | 0.1295 (8) | 0.050* | |
O2W | 0.0195 (3) | 0.09867 (17) | 0.05014 (14) | 0.0781 (7) | |
H3W | 0.043 (4) | 0.073 (3) | 0.0998 (10) | 0.094* | |
H4W | −0.040 (7) | 0.043 (3) | 0.025 (2) | 0.094* | 0.5 |
H5W | 0.114 (5) | 0.085 (6) | 0.038 (3) | 0.094* | 0.5 |
H1H | 0.260 (4) | 0.065 (2) | 0.8945 (19) | 0.074 (11)* | |
H2H | 0.704 (4) | −0.099 (2) | 0.7780 (17) | 0.053 (9)* | |
H3H | 0.461 (4) | 0.469 (2) | 0.0886 (18) | 0.068 (11)* | |
H4H | 0.482 (4) | 0.626 (2) | 0.0679 (17) | 0.062 (9)* | |
H1N | 0.050 (3) | 0.3194 (18) | −0.0005 (15) | 0.035 (7)* | |
H2N | 0.145 (3) | 0.373 (2) | −0.0441 (15) | 0.047 (8)* | |
H3N | 0.095 (3) | 0.260 (2) | −0.0613 (17) | 0.046 (8)* | |
H4N | 0.234 (5) | 0.274 (3) | 0.021 (2) | 0.104 (12)* | |
H5N | 0.703 (3) | 0.133 (2) | 0.9597 (17) | 0.051 (8)* | |
H6N | 0.561 (5) | 0.176 (3) | 0.985 (2) | 0.089 (12)* | |
H7N | 0.724 (4) | 0.209 (3) | 1.0321 (19) | 0.076 (10)* | |
H8N | 0.642 (4) | 0.094 (2) | 1.0311 (18) | 0.068 (9)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0168 (3) | 0.0223 (3) | 0.0236 (3) | 0.0022 (2) | 0.0046 (2) | 0.0025 (2) |
S1A | 0.0208 (3) | 0.0229 (3) | 0.0204 (3) | 0.0026 (2) | 0.0060 (2) | 0.0013 (2) |
O1 | 0.0154 (8) | 0.0475 (10) | 0.0362 (9) | 0.0040 (7) | 0.0054 (7) | 0.0123 (7) |
O1A | 0.0321 (9) | 0.0203 (8) | 0.0336 (9) | −0.0030 (6) | 0.0027 (7) | 0.0030 (6) |
O2 | 0.0352 (9) | 0.0209 (8) | 0.0338 (9) | 0.0033 (7) | 0.0052 (7) | 0.0063 (6) |
O2A | 0.0398 (10) | 0.0631 (12) | 0.0252 (9) | 0.0237 (9) | 0.0168 (8) | 0.0112 (8) |
O3 | 0.0302 (9) | 0.0301 (8) | 0.0225 (8) | 0.0062 (7) | 0.0054 (7) | −0.0005 (6) |
O3A | 0.0230 (8) | 0.0249 (8) | 0.0293 (8) | −0.0019 (6) | −0.0002 (6) | 0.0015 (6) |
O4 | 0.0336 (10) | 0.0337 (9) | 0.0266 (9) | 0.0067 (8) | 0.0072 (7) | 0.0019 (7) |
O4A | 0.0287 (9) | 0.0379 (9) | 0.0254 (9) | 0.0094 (8) | 0.0091 (7) | 0.0008 (7) |
O5 | 0.0239 (9) | 0.0340 (9) | 0.0295 (9) | −0.0038 (7) | 0.0041 (7) | 0.0016 (7) |
O5A | 0.0416 (10) | 0.0343 (10) | 0.0299 (9) | 0.0067 (8) | 0.0155 (8) | 0.0070 (7) |
N1 | 0.0200 (9) | 0.0224 (9) | 0.0235 (9) | 0.0030 (7) | 0.0042 (7) | 0.0002 (7) |
N1A | 0.0293 (11) | 0.0220 (9) | 0.0219 (9) | 0.0034 (8) | 0.0084 (8) | −0.0004 (7) |
N2 | 0.0241 (10) | 0.0210 (9) | 0.0248 (10) | 0.0033 (8) | 0.0036 (8) | 0.0017 (7) |
N2A | 0.0285 (10) | 0.0212 (9) | 0.0216 (9) | 0.0043 (8) | 0.0098 (8) | −0.0005 (7) |
N3 | 0.0216 (10) | 0.0212 (9) | 0.0217 (9) | 0.0042 (7) | 0.0051 (7) | 0.0028 (7) |
N3A | 0.0193 (9) | 0.0204 (9) | 0.0209 (9) | −0.0010 (7) | 0.0047 (7) | 0.0007 (7) |
N4 | 0.0379 (13) | 0.0289 (12) | 0.0270 (11) | −0.0040 (10) | 0.0154 (10) | −0.0051 (10) |
N5 | 0.0321 (13) | 0.0323 (12) | 0.0232 (11) | 0.0018 (10) | 0.0088 (9) | 0.0012 (9) |
C1 | 0.0148 (10) | 0.0180 (10) | 0.0231 (11) | −0.0012 (8) | 0.0050 (8) | 0.0019 (8) |
C1A | 0.0208 (11) | 0.0208 (10) | 0.0201 (11) | 0.0046 (8) | 0.0076 (9) | −0.0018 (8) |
C2 | 0.0229 (12) | 0.0175 (10) | 0.0286 (12) | 0.0041 (8) | 0.0061 (9) | 0.0003 (9) |
C2A | 0.0249 (12) | 0.0192 (10) | 0.0240 (11) | −0.0007 (9) | 0.0071 (9) | −0.0014 (8) |
C3 | 0.0227 (11) | 0.0202 (11) | 0.0243 (11) | 0.0002 (9) | 0.0078 (9) | −0.0038 (8) |
C3A | 0.0236 (12) | 0.0227 (11) | 0.0234 (11) | 0.0013 (9) | 0.0044 (9) | −0.0026 (9) |
C4 | 0.0160 (10) | 0.0201 (10) | 0.0223 (11) | −0.0017 (8) | 0.0037 (8) | 0.0003 (8) |
C4A | 0.0254 (12) | 0.0216 (11) | 0.0200 (11) | 0.0055 (9) | 0.0073 (9) | −0.0012 (8) |
C5 | 0.0168 (11) | 0.0217 (11) | 0.0257 (11) | 0.0054 (8) | 0.0038 (9) | 0.0004 (9) |
C5A | 0.0258 (12) | 0.0215 (11) | 0.0287 (12) | 0.0004 (9) | 0.0101 (9) | 0.0030 (9) |
C6 | 0.0170 (11) | 0.0249 (11) | 0.0246 (11) | 0.0030 (9) | 0.0053 (9) | −0.0027 (9) |
C6A | 0.0215 (11) | 0.0252 (11) | 0.0249 (11) | 0.0005 (9) | 0.0056 (9) | −0.0008 (9) |
C7 | 0.0211 (11) | 0.0233 (11) | 0.0208 (11) | 0.0024 (9) | 0.0015 (9) | 0.0007 (8) |
C7A | 0.0248 (12) | 0.0219 (11) | 0.0185 (11) | 0.0055 (9) | 0.0055 (9) | −0.0011 (8) |
C8 | 0.0299 (13) | 0.0243 (11) | 0.0224 (11) | 0.0040 (9) | 0.0074 (9) | −0.0016 (9) |
C8A | 0.0212 (11) | 0.0238 (11) | 0.0224 (11) | 0.0031 (9) | 0.0042 (9) | −0.0008 (9) |
C9 | 0.0276 (12) | 0.0218 (11) | 0.0240 (11) | 0.0051 (9) | 0.0049 (9) | −0.0024 (9) |
C9A | 0.0225 (11) | 0.0195 (10) | 0.0237 (11) | −0.0010 (8) | 0.0078 (9) | −0.0006 (8) |
C10 | 0.0160 (11) | 0.0218 (11) | 0.0222 (11) | −0.0002 (8) | 0.0022 (8) | −0.0010 (8) |
C10A | 0.0218 (11) | 0.0189 (10) | 0.0201 (11) | 0.0041 (8) | 0.0091 (9) | −0.0021 (8) |
C11 | 0.0219 (11) | 0.0276 (11) | 0.0210 (11) | 0.0029 (9) | 0.0073 (9) | −0.0019 (9) |
C11A | 0.0224 (11) | 0.0215 (11) | 0.0222 (11) | 0.0002 (9) | 0.0058 (9) | −0.0026 (8) |
C12 | 0.0198 (11) | 0.0222 (11) | 0.0249 (11) | 0.0040 (9) | 0.0031 (9) | −0.0014 (9) |
C12A | 0.0296 (13) | 0.0178 (10) | 0.0253 (11) | −0.0003 (9) | 0.0132 (9) | −0.0013 (8) |
C13 | 0.0253 (12) | 0.0234 (11) | 0.0237 (11) | 0.0000 (9) | 0.0077 (9) | 0.0031 (9) |
C13A | 0.0209 (11) | 0.0288 (12) | 0.0218 (11) | 0.0010 (9) | 0.0044 (9) | −0.0014 (9) |
C14 | 0.0289 (13) | 0.0244 (11) | 0.0233 (12) | 0.0011 (9) | 0.0056 (9) | −0.0009 (9) |
C14A | 0.0258 (13) | 0.0357 (13) | 0.0278 (12) | −0.0045 (10) | 0.0081 (10) | −0.0087 (10) |
C15 | 0.0260 (12) | 0.0177 (10) | 0.0266 (12) | 0.0018 (9) | 0.0046 (9) | 0.0022 (8) |
C15A | 0.0233 (12) | 0.0209 (11) | 0.0257 (12) | 0.0041 (9) | 0.0055 (9) | 0.0031 (9) |
C16 | 0.0278 (13) | 0.0239 (11) | 0.0271 (12) | 0.0039 (9) | 0.0064 (10) | −0.0012 (9) |
C16A | 0.0239 (12) | 0.0262 (12) | 0.0343 (13) | 0.0024 (9) | 0.0091 (10) | 0.0046 (10) |
O1W | 0.0530 (12) | 0.0355 (10) | 0.0374 (10) | 0.0040 (8) | 0.0141 (9) | 0.0100 (8) |
O2W | 0.114 (2) | 0.0569 (14) | 0.0507 (14) | −0.0083 (15) | −0.0009 (13) | 0.0128 (11) |
S1—O2 | 1.4431 (15) | C5—H5 | 0.9500 |
S1—O1 | 1.4566 (15) | C5A—C6A | 1.389 (3) |
S1—O3 | 1.4592 (15) | C5A—H5A | 0.9500 |
S1—C1 | 1.770 (2) | C6—H6 | 0.9500 |
S1A—O2A | 1.4462 (16) | C6A—H6A | 0.9500 |
S1A—O3A | 1.4559 (15) | C7—C8 | 1.390 (3) |
S1A—O1A | 1.4579 (15) | C7—C12 | 1.399 (3) |
S1A—C1A | 1.765 (2) | C7A—C8A | 1.394 (3) |
O4—C14 | 1.420 (3) | C7A—C12A | 1.397 (3) |
O4—H1H | 0.84 (3) | C8—C9 | 1.381 (3) |
O4A—C14A | 1.429 (3) | C8—H8 | 0.9500 |
O4A—H3H | 0.80 (3) | C8A—C9A | 1.380 (3) |
O5—C16 | 1.424 (3) | C8A—H8A | 0.9500 |
O5—H2H | 0.81 (3) | C9—C10 | 1.408 (3) |
O5A—C16A | 1.428 (3) | C9—H9 | 0.9500 |
O5A—H4H | 0.97 (3) | C9A—C10A | 1.411 (3) |
N1—N2 | 1.264 (2) | C9A—H9A | 0.9500 |
N1—C4 | 1.439 (2) | C10—C11 | 1.421 (3) |
N1A—N2A | 1.261 (2) | C10A—C11A | 1.422 (3) |
N1A—C4A | 1.430 (3) | C11—C12 | 1.373 (3) |
N2—C7 | 1.405 (2) | C11—H11 | 0.9500 |
N2A—C7A | 1.416 (3) | C11A—C12A | 1.371 (3) |
N3—C10 | 1.374 (2) | C11A—H11A | 0.9500 |
N3—C13 | 1.460 (3) | C12—H12 | 0.9500 |
N3—C15 | 1.464 (3) | C12A—H12A | 0.9500 |
N3A—C10A | 1.373 (2) | C13—C14 | 1.518 (3) |
N3A—C15A | 1.455 (2) | C13—H13A | 0.9900 |
N3A—C13A | 1.467 (3) | C13—H13B | 0.9900 |
N4—H1N | 0.87 (3) | C13A—C14A | 1.513 (3) |
N4—H2N | 0.95 (3) | C13A—H13C | 0.9900 |
N4—H3N | 0.89 (3) | C13A—H13D | 0.9900 |
N4—H4N | 1.13 (4) | C14—H14A | 0.9900 |
N5—H5N | 0.91 (3) | C14—H14B | 0.9900 |
N5—H6N | 0.89 (4) | C14A—H14C | 0.9900 |
N5—H7N | 0.96 (4) | C14A—H14D | 0.9900 |
N5—H8N | 0.96 (3) | C15—C16 | 1.509 (3) |
C1—C2 | 1.392 (3) | C15—H15A | 0.9900 |
C1—C6 | 1.397 (3) | C15—H15B | 0.9900 |
C1A—C2A | 1.389 (3) | C15A—C16A | 1.516 (3) |
C1A—C6A | 1.397 (3) | C15A—H15C | 0.9900 |
C2—C3 | 1.384 (3) | C15A—H15D | 0.9900 |
C2—H2 | 0.9500 | C16—H16A | 0.9900 |
C2A—C3A | 1.379 (3) | C16—H16B | 0.9900 |
C2A—H2A | 0.9500 | C16A—H16C | 0.9900 |
C3—C4 | 1.393 (3) | C16A—H16D | 0.9900 |
C3—H3 | 0.9500 | O1W—H1W | 0.875 (10) |
C3A—C4A | 1.390 (3) | O1W—H2W | 0.882 (9) |
C3A—H3A | 0.9500 | O2W—H3W | 0.907 (10) |
C4—C5 | 1.387 (3) | O2W—H4W | 0.889 (10) |
C4A—C5A | 1.393 (3) | O2W—H5W | 0.899 (10) |
C5—C6 | 1.380 (3) | ||
O2—S1—O1 | 112.96 (9) | C9—C8—H8 | 119.1 |
O2—S1—O3 | 113.85 (9) | C7—C8—H8 | 119.1 |
O1—S1—O3 | 111.27 (9) | C9A—C8A—C7A | 121.04 (19) |
O2—S1—C1 | 107.12 (9) | C9A—C8A—H8A | 119.5 |
O1—S1—C1 | 104.63 (9) | C7A—C8A—H8A | 119.5 |
O3—S1—C1 | 106.25 (9) | C8—C9—C10 | 120.62 (19) |
O2A—S1A—O3A | 112.58 (10) | C8—C9—H9 | 119.7 |
O2A—S1A—O1A | 112.66 (10) | C10—C9—H9 | 119.7 |
O3A—S1A—O1A | 111.19 (9) | C8A—C9A—C10A | 121.12 (18) |
O2A—S1A—C1A | 105.65 (9) | C8A—C9A—H9A | 119.4 |
O3A—S1A—C1A | 107.50 (9) | C10A—C9A—H9A | 119.4 |
O1A—S1A—C1A | 106.79 (9) | N3—C10—C9 | 121.13 (18) |
C14—O4—H1H | 109 (2) | N3—C10—C11 | 121.97 (18) |
C14A—O4A—H3H | 106 (2) | C9—C10—C11 | 116.90 (18) |
C16—O5—H2H | 107 (2) | N3A—C10A—C9A | 121.74 (17) |
C16A—O5A—H4H | 106.9 (17) | N3A—C10A—C11A | 121.25 (18) |
N2—N1—C4 | 111.31 (16) | C9A—C10A—C11A | 116.99 (18) |
N2A—N1A—C4A | 113.71 (17) | C12—C11—C10 | 121.86 (19) |
N1—N2—C7 | 116.79 (17) | C12—C11—H11 | 119.1 |
N1A—N2A—C7A | 113.68 (17) | C10—C11—H11 | 119.1 |
C10—N3—C13 | 121.50 (17) | C12A—C11A—C10A | 121.17 (19) |
C10—N3—C15 | 120.47 (17) | C12A—C11A—H11A | 119.4 |
C13—N3—C15 | 117.88 (16) | C10A—C11A—H11A | 119.4 |
C10A—N3A—C15A | 120.69 (17) | C11—C12—C7 | 120.38 (19) |
C10A—N3A—C13A | 121.44 (16) | C11—C12—H12 | 119.8 |
C15A—N3A—C13A | 117.84 (16) | C7—C12—H12 | 119.8 |
H1N—N4—H2N | 98 (2) | C11A—C12A—C7A | 121.10 (19) |
H1N—N4—H3N | 108 (2) | C11A—C12A—H12A | 119.5 |
H2N—N4—H3N | 109 (2) | C7A—C12A—H12A | 119.5 |
H1N—N4—H4N | 114 (2) | N3—C13—C14 | 114.18 (17) |
H2N—N4—H4N | 122 (2) | N3—C13—H13A | 108.7 |
H3N—N4—H4N | 105 (2) | C14—C13—H13A | 108.7 |
H5N—N5—H6N | 114 (3) | N3—C13—H13B | 108.7 |
H5N—N5—H7N | 111 (3) | C14—C13—H13B | 108.7 |
H6N—N5—H7N | 104 (3) | H13A—C13—H13B | 107.6 |
H5N—N5—H8N | 108 (2) | N3A—C13A—C14A | 114.69 (17) |
H6N—N5—H8N | 106 (3) | N3A—C13A—H13C | 108.6 |
H7N—N5—H8N | 114 (3) | C14A—C13A—H13C | 108.6 |
C2—C1—C6 | 119.76 (18) | N3A—C13A—H13D | 108.6 |
C2—C1—S1 | 119.93 (15) | C14A—C13A—H13D | 108.6 |
C6—C1—S1 | 119.99 (16) | H13C—C13A—H13D | 107.6 |
C2A—C1A—C6A | 120.26 (18) | O4—C14—C13 | 110.98 (17) |
C2A—C1A—S1A | 118.50 (15) | O4—C14—H14A | 109.4 |
C6A—C1A—S1A | 121.11 (16) | C13—C14—H14A | 109.4 |
C3—C2—C1 | 120.12 (18) | O4—C14—H14B | 109.4 |
C3—C2—H2 | 119.9 | C13—C14—H14B | 109.4 |
C1—C2—H2 | 119.9 | H14A—C14—H14B | 108.0 |
C3A—C2A—C1A | 119.88 (19) | O4A—C14A—C13A | 112.62 (18) |
C3A—C2A—H2A | 120.1 | O4A—C14A—H14C | 109.1 |
C1A—C2A—H2A | 120.1 | C13A—C14A—H14C | 109.1 |
C2—C3—C4 | 119.95 (19) | O4A—C14A—H14D | 109.1 |
C2—C3—H3 | 120.0 | C13A—C14A—H14D | 109.1 |
C4—C3—H3 | 120.0 | H14C—C14A—H14D | 107.8 |
C2A—C3A—C4A | 120.4 (2) | N3—C15—C16 | 114.16 (17) |
C2A—C3A—H3A | 119.8 | N3—C15—H15A | 108.7 |
C4A—C3A—H3A | 119.8 | C16—C15—H15A | 108.7 |
C5—C4—C3 | 119.75 (18) | N3—C15—H15B | 108.7 |
C5—C4—N1 | 123.30 (17) | C16—C15—H15B | 108.7 |
C3—C4—N1 | 116.82 (18) | H15A—C15—H15B | 107.6 |
C3A—C4A—C5A | 119.94 (18) | N3A—C15A—C16A | 115.20 (17) |
C3A—C4A—N1A | 114.97 (18) | N3A—C15A—H15C | 108.5 |
C5A—C4A—N1A | 125.08 (18) | C16A—C15A—H15C | 108.5 |
C6—C5—C4 | 120.56 (18) | N3A—C15A—H15D | 108.5 |
C6—C5—H5 | 119.7 | C16A—C15A—H15D | 108.5 |
C4—C5—H5 | 119.7 | H15C—C15A—H15D | 107.5 |
C6A—C5A—C4A | 119.94 (19) | O5—C16—C15 | 109.56 (18) |
C6A—C5A—H5A | 120.0 | O5—C16—H16A | 109.8 |
C4A—C5A—H5A | 120.0 | C15—C16—H16A | 109.8 |
C5—C6—C1 | 119.72 (19) | O5—C16—H16B | 109.8 |
C5—C6—H6 | 120.1 | C15—C16—H16B | 109.8 |
C1—C6—H6 | 120.1 | H16A—C16—H16B | 108.2 |
C5A—C6A—C1A | 119.6 (2) | O5A—C16A—C15A | 113.46 (18) |
C5A—C6A—H6A | 120.2 | O5A—C16A—H16C | 108.9 |
C1A—C6A—H6A | 120.2 | C15A—C16A—H16C | 108.9 |
C8—C7—C12 | 118.44 (18) | O5A—C16A—H16D | 108.9 |
C8—C7—N2 | 114.54 (18) | C15A—C16A—H16D | 108.9 |
C12—C7—N2 | 126.97 (18) | H16C—C16A—H16D | 107.7 |
C8A—C7A—C12A | 118.49 (18) | H1W—O1W—H2W | 99.8 (17) |
C8A—C7A—N2A | 116.70 (18) | H3W—O2W—H4W | 97 (2) |
C12A—C7A—N2A | 124.81 (18) | H3W—O2W—H5W | 95 (2) |
C9—C8—C7 | 121.8 (2) | H4W—O2W—H5W | 97 (7) |
C4—N1—N2—C7 | −176.00 (16) | N1A—N2A—C7A—C12A | 7.7 (3) |
C4A—N1A—N2A—C7A | −177.76 (16) | C12—C7—C8—C9 | −1.6 (3) |
O2—S1—C1—C2 | 56.35 (18) | N2—C7—C8—C9 | −179.29 (19) |
O1—S1—C1—C2 | −63.79 (18) | C12A—C7A—C8A—C9A | −3.7 (3) |
O3—S1—C1—C2 | 178.39 (16) | N2A—C7A—C8A—C9A | 177.34 (18) |
O2—S1—C1—C6 | −130.20 (16) | C7—C8—C9—C10 | 1.5 (3) |
O1—S1—C1—C6 | 109.65 (17) | C7A—C8A—C9A—C10A | 1.5 (3) |
O3—S1—C1—C6 | −8.16 (19) | C13—N3—C10—C9 | 179.78 (19) |
O2A—S1A—C1A—C2A | −69.61 (18) | C15—N3—C10—C9 | −4.7 (3) |
O3A—S1A—C1A—C2A | 169.97 (15) | C13—N3—C10—C11 | −0.8 (3) |
O1A—S1A—C1A—C2A | 50.56 (18) | C15—N3—C10—C11 | 174.65 (18) |
O2A—S1A—C1A—C6A | 106.12 (18) | C8—C9—C10—N3 | 178.38 (19) |
O3A—S1A—C1A—C6A | −14.30 (19) | C8—C9—C10—C11 | −1.0 (3) |
O1A—S1A—C1A—C6A | −133.71 (17) | C15A—N3A—C10A—C9A | −4.9 (3) |
C6—C1—C2—C3 | −1.9 (3) | C13A—N3A—C10A—C9A | 173.20 (18) |
S1—C1—C2—C3 | 171.55 (15) | C15A—N3A—C10A—C11A | 173.48 (18) |
C6A—C1A—C2A—C3A | 0.0 (3) | C13A—N3A—C10A—C11A | −8.4 (3) |
S1A—C1A—C2A—C3A | 175.81 (16) | C8A—C9A—C10A—N3A | 179.49 (18) |
C1—C2—C3—C4 | −1.4 (3) | C8A—C9A—C10A—C11A | 1.1 (3) |
C1A—C2A—C3A—C4A | 0.2 (3) | N3—C10—C11—C12 | −178.63 (19) |
C2—C3—C4—C5 | 3.4 (3) | C9—C10—C11—C12 | 0.8 (3) |
C2—C3—C4—N1 | −172.66 (18) | N3A—C10A—C11A—C12A | −179.79 (18) |
N2—N1—C4—C5 | 4.0 (3) | C9A—C10A—C11A—C12A | −1.4 (3) |
N2—N1—C4—C3 | 179.91 (18) | C10—C11—C12—C7 | −0.9 (3) |
C2A—C3A—C4A—C5A | −0.3 (3) | C8—C7—C12—C11 | 1.3 (3) |
C2A—C3A—C4A—N1A | −179.21 (18) | N2—C7—C12—C11 | 178.69 (19) |
N2A—N1A—C4A—C3A | 174.69 (17) | C10A—C11A—C12A—C7A | −0.9 (3) |
N2A—N1A—C4A—C5A | −4.2 (3) | C8A—C7A—C12A—C11A | 3.4 (3) |
C3—C4—C5—C6 | −2.2 (3) | N2A—C7A—C12A—C11A | −177.73 (19) |
N1—C4—C5—C6 | 173.63 (18) | C10—N3—C13—C14 | −81.0 (2) |
C3A—C4A—C5A—C6A | 0.2 (3) | C15—N3—C13—C14 | 103.4 (2) |
N1A—C4A—C5A—C6A | 179.01 (19) | C10A—N3A—C13A—C14A | −71.0 (2) |
C4—C5—C6—C1 | −1.1 (3) | C15A—N3A—C13A—C14A | 107.2 (2) |
C2—C1—C6—C5 | 3.2 (3) | N3—C13—C14—O4 | −179.84 (16) |
S1—C1—C6—C5 | −170.31 (15) | N3A—C13A—C14A—O4A | −66.8 (2) |
C4A—C5A—C6A—C1A | 0.0 (3) | C10—N3—C15—C16 | 84.3 (2) |
C2A—C1A—C6A—C5A | −0.1 (3) | C13—N3—C15—C16 | −100.0 (2) |
S1A—C1A—C6A—C5A | −175.79 (16) | C10A—N3A—C15A—C16A | 90.8 (2) |
N1—N2—C7—C8 | −178.25 (18) | C13A—N3A—C15A—C16A | −87.4 (2) |
N1—N2—C7—C12 | 4.3 (3) | N3—C15—C16—O5 | 66.0 (2) |
N1A—N2A—C7A—C8A | −173.40 (18) | N3A—C15A—C16A—O5A | 85.7 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W···O1i | 0.88 (1) | 1.93 (1) | 2.802 (2) | 176 (3) |
O1W—H2W···O5ii | 0.88 (1) | 1.84 (1) | 2.711 (2) | 168 (2) |
O2W—H3W···O1Aii | 0.91 (1) | 2.05 (1) | 2.945 (2) | 172 (3) |
O2W—H4W···O2Wiii | 0.89 (1) | 2.29 (4) | 3.031 (5) | 141 (6) |
O4—H1H···O3Aiv | 0.84 (3) | 2.05 (3) | 2.885 (2) | 169 (3) |
O5—H2H···O1A | 0.81 (3) | 1.90 (3) | 2.698 (2) | 169 (3) |
O4A—H3H···O1i | 0.80 (3) | 1.96 (3) | 2.756 (2) | 177 (3) |
O5A—H4H···O4A | 0.97 (3) | 1.79 (3) | 2.734 (2) | 165 (3) |
N4—H1N···O3 | 0.87 (3) | 2.09 (3) | 2.957 (3) | 176 (2) |
N4—H2N···O2v | 0.95 (3) | 1.92 (3) | 2.841 (3) | 163 (2) |
N4—H3N···O3Avi | 0.89 (3) | 2.05 (3) | 2.923 (3) | 167 (2) |
N4—H4N···O1W | 1.13 (4) | 1.69 (4) | 2.818 (3) | 176 (3) |
N5—H5N···O2A | 0.91 (3) | 1.89 (3) | 2.784 (3) | 164 (2) |
N5—H6N···O5Avii | 0.89 (4) | 2.21 (4) | 2.935 (3) | 138 (3) |
N5—H6N···O1Wviii | 0.89 (4) | 2.51 (4) | 3.094 (3) | 123 (3) |
N5—H7N···O3ix | 0.96 (4) | 2.03 (4) | 2.952 (3) | 159 (3) |
N5—H8N···O4x | 0.96 (3) | 2.00 (3) | 2.943 (3) | 168 (3) |
Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y, −z+1; (iii) −x, −y, −z; (iv) x−1, y, z; (v) −x, −y+1, −z; (vi) x−1, y, z−1; (vii) −x+1, −y+1, −z+1; (viii) x, y, z+1; (ix) x+1, y, z+1; (x) −x+1, −y, −z+2. |
NH4+·C12H9N2O4S− | Dx = 1.533 Mg m−3 |
Mr = 295.31 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pccn | Cell parameters from 3229 reflections |
a = 12.6592 (3) Å | θ = 1.0–27.5° |
b = 28.3597 (7) Å | µ = 0.27 mm−1 |
c = 7.1268 (2) Å | T = 123 K |
V = 2558.60 (11) Å3 | Cut needle, yellow-orange |
Z = 8 | 0.30 × 0.10 × 0.05 mm |
F(000) = 1232 |
Enraf–Nonius KappaCCD diffractometer | Rint = 0.069 |
Radiation source: sealed tube | θmax = 27.5°, θmin = 1.8° |
phi and ω scans | h = −16→16 |
5346 measured reflections | k = −36→36 |
2923 independent reflections | l = −9→9 |
1850 reflections with I > 2σ(I) |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.051 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.118 | w = 1/[σ2(Fo2) + (0.0361P)2 + 2.7325P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
2923 reflections | Δρmax = 0.29 e Å−3 |
201 parameters | Δρmin = −0.45 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.94027 (5) | 0.56239 (2) | 0.18127 (9) | 0.01749 (18) | |
O1 | 0.85668 (15) | 0.55115 (7) | 0.0463 (3) | 0.0287 (5) | |
O2 | 1.04360 (14) | 0.56367 (7) | 0.0953 (3) | 0.0278 (5) | |
O3 | 0.93547 (16) | 0.53174 (7) | 0.3437 (3) | 0.0301 (5) | |
O4 | 1.24530 (16) | 0.93197 (7) | 0.0369 (3) | 0.0255 (5) | |
N1 | 1.02393 (17) | 0.73916 (8) | 0.2062 (3) | 0.0203 (5) | |
N2 | 0.99241 (18) | 0.78005 (9) | 0.2434 (3) | 0.0203 (5) | |
N3 | 0.6639 (2) | 0.50958 (11) | 0.1885 (4) | 0.0229 (6) | |
C1 | 0.9119 (2) | 0.62035 (10) | 0.2584 (3) | 0.0168 (6) | |
C2 | 0.9772 (2) | 0.65733 (10) | 0.2101 (4) | 0.0180 (6) | |
H2 | 1.039750 | 0.651624 | 0.139888 | 0.022* | |
C3 | 0.9512 (2) | 0.70309 (10) | 0.2644 (4) | 0.0176 (6) | |
C4 | 0.8602 (2) | 0.71133 (10) | 0.3688 (4) | 0.0206 (6) | |
H4 | 0.842341 | 0.742487 | 0.406115 | 0.025* | |
C5 | 0.7955 (2) | 0.67381 (10) | 0.4181 (4) | 0.0222 (7) | |
H5 | 0.733423 | 0.679368 | 0.489583 | 0.027* | |
C6 | 0.8209 (2) | 0.62841 (10) | 0.3640 (4) | 0.0202 (6) | |
H6 | 0.776597 | 0.602809 | 0.398488 | 0.024* | |
C7 | 1.0619 (2) | 0.81667 (10) | 0.1844 (4) | 0.0181 (6) | |
C8 | 1.1588 (2) | 0.80929 (10) | 0.0944 (4) | 0.0220 (6) | |
H8 | 1.181883 | 0.778107 | 0.068094 | 0.026* | |
C9 | 1.2208 (2) | 0.84727 (10) | 0.0436 (4) | 0.0208 (6) | |
H9 | 1.286594 | 0.842325 | −0.017454 | 0.025* | |
C10 | 1.1862 (2) | 0.89298 (10) | 0.0825 (4) | 0.0182 (6) | |
C11 | 1.0895 (2) | 0.90081 (10) | 0.1682 (4) | 0.0200 (6) | |
H11 | 1.065732 | 0.932015 | 0.191929 | 0.024* | |
C12 | 1.0278 (2) | 0.86232 (10) | 0.2188 (4) | 0.0191 (6) | |
H12 | 0.961388 | 0.867354 | 0.277683 | 0.023* | |
H1N | 0.673 (3) | 0.4784 (13) | 0.204 (5) | 0.042 (10)* | |
H2N | 0.731 (3) | 0.5206 (11) | 0.146 (5) | 0.046 (10)* | |
H3N | 0.641 (2) | 0.5235 (11) | 0.292 (4) | 0.026 (8)* | |
H4N | 0.619 (3) | 0.5176 (12) | 0.096 (5) | 0.048 (11)* | |
H1H | 1.306 (3) | 0.9239 (14) | 0.020 (6) | 0.063 (13)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0153 (3) | 0.0193 (3) | 0.0179 (3) | 0.0001 (3) | 0.0004 (3) | 0.0010 (3) |
O1 | 0.0239 (11) | 0.0337 (13) | 0.0287 (11) | 0.0064 (9) | −0.0101 (9) | −0.0126 (10) |
O2 | 0.0172 (10) | 0.0255 (11) | 0.0407 (12) | 0.0015 (9) | 0.0095 (9) | 0.0013 (10) |
O3 | 0.0488 (13) | 0.0207 (11) | 0.0208 (10) | 0.0014 (10) | 0.0054 (10) | 0.0055 (9) |
O4 | 0.0188 (10) | 0.0256 (12) | 0.0319 (11) | −0.0016 (10) | 0.0045 (10) | 0.0032 (10) |
N1 | 0.0191 (11) | 0.0208 (13) | 0.0211 (12) | −0.0016 (10) | −0.0006 (10) | −0.0001 (11) |
N2 | 0.0211 (13) | 0.0203 (13) | 0.0194 (12) | −0.0017 (11) | −0.0025 (9) | 0.0018 (10) |
N3 | 0.0259 (14) | 0.0243 (15) | 0.0185 (13) | 0.0008 (12) | 0.0015 (13) | −0.0021 (13) |
C1 | 0.0166 (14) | 0.0197 (15) | 0.0141 (13) | 0.0011 (12) | −0.0008 (11) | 0.0025 (12) |
C2 | 0.0138 (13) | 0.0220 (15) | 0.0182 (14) | 0.0010 (12) | −0.0001 (11) | −0.0002 (12) |
C3 | 0.0135 (13) | 0.0231 (15) | 0.0163 (13) | −0.0053 (12) | −0.0040 (11) | 0.0036 (12) |
C4 | 0.0185 (13) | 0.0198 (16) | 0.0235 (14) | 0.0025 (12) | −0.0007 (12) | −0.0006 (13) |
C5 | 0.0168 (14) | 0.0278 (18) | 0.0218 (15) | 0.0033 (12) | 0.0023 (12) | 0.0002 (13) |
C6 | 0.0165 (13) | 0.0239 (16) | 0.0200 (14) | −0.0017 (12) | −0.0003 (12) | 0.0025 (13) |
C7 | 0.0173 (12) | 0.0212 (14) | 0.0156 (13) | −0.0023 (12) | −0.0055 (12) | −0.0001 (12) |
C8 | 0.0217 (14) | 0.0219 (16) | 0.0225 (15) | 0.0016 (12) | −0.0022 (12) | −0.0031 (13) |
C9 | 0.0162 (14) | 0.0270 (17) | 0.0193 (14) | 0.0004 (12) | 0.0000 (11) | −0.0023 (13) |
C10 | 0.0172 (14) | 0.0211 (16) | 0.0163 (14) | −0.0034 (12) | −0.0031 (11) | 0.0014 (12) |
C11 | 0.0193 (13) | 0.0186 (15) | 0.0222 (14) | 0.0020 (11) | −0.0021 (12) | 0.0007 (13) |
C12 | 0.0158 (13) | 0.0241 (16) | 0.0174 (13) | −0.0008 (12) | −0.0015 (11) | −0.0007 (13) |
S1—O2 | 1.4449 (19) | C3—C4 | 1.392 (4) |
S1—O3 | 1.449 (2) | C4—C5 | 1.387 (4) |
S1—O1 | 1.4648 (19) | C4—H4 | 0.9500 |
S1—C1 | 1.770 (3) | C5—C6 | 1.382 (4) |
O4—C10 | 1.374 (3) | C5—H5 | 0.9500 |
O4—H1H | 0.82 (4) | C6—H6 | 0.9500 |
N1—N2 | 1.254 (3) | C7—C12 | 1.387 (4) |
N1—C3 | 1.437 (3) | C7—C8 | 1.400 (4) |
N2—C7 | 1.425 (3) | C8—C9 | 1.381 (4) |
N3—H1N | 0.90 (4) | C8—H8 | 0.9500 |
N3—H2N | 0.96 (4) | C9—C10 | 1.396 (4) |
N3—H3N | 0.89 (3) | C9—H9 | 0.9500 |
N3—H4N | 0.90 (4) | C10—C11 | 1.386 (4) |
C1—C2 | 1.379 (4) | C11—C12 | 1.390 (4) |
C1—C6 | 1.395 (4) | C11—H11 | 0.9500 |
C2—C3 | 1.394 (4) | C12—H12 | 0.9500 |
C2—H2 | 0.9500 | ||
O2—S1—O3 | 113.06 (12) | C3—C4—H4 | 120.2 |
O2—S1—O1 | 112.41 (12) | C6—C5—C4 | 120.4 (3) |
O3—S1—O1 | 111.33 (12) | C6—C5—H5 | 119.8 |
O2—S1—C1 | 106.97 (12) | C4—C5—H5 | 119.8 |
O3—S1—C1 | 107.48 (12) | C5—C6—C1 | 119.7 (3) |
O1—S1—C1 | 105.04 (12) | C5—C6—H6 | 120.2 |
C10—O4—H1H | 109 (3) | C1—C6—H6 | 120.2 |
N2—N1—C3 | 113.2 (2) | C12—C7—C8 | 119.6 (3) |
N1—N2—C7 | 114.5 (2) | C12—C7—N2 | 115.9 (2) |
H1N—N3—H2N | 105 (3) | C8—C7—N2 | 124.6 (2) |
H1N—N3—H3N | 112 (3) | C9—C8—C7 | 120.1 (3) |
H2N—N3—H3N | 114 (3) | C9—C8—H8 | 120.0 |
H1N—N3—H4N | 114 (3) | C7—C8—H8 | 120.0 |
H2N—N3—H4N | 105 (3) | C8—C9—C10 | 119.6 (3) |
H3N—N3—H4N | 107 (3) | C8—C9—H9 | 120.2 |
C2—C1—C6 | 120.4 (3) | C10—C9—H9 | 120.2 |
C2—C1—S1 | 120.5 (2) | O4—C10—C11 | 117.1 (2) |
C6—C1—S1 | 119.2 (2) | O4—C10—C9 | 122.0 (2) |
C1—C2—C3 | 119.8 (2) | C11—C10—C9 | 120.9 (3) |
C1—C2—H2 | 120.1 | C10—C11—C12 | 119.0 (3) |
C3—C2—H2 | 120.1 | C10—C11—H11 | 120.5 |
C4—C3—C2 | 120.0 (2) | C12—C11—H11 | 120.5 |
C4—C3—N1 | 124.4 (3) | C7—C12—C11 | 120.8 (3) |
C2—C3—N1 | 115.6 (2) | C7—C12—H12 | 119.6 |
C5—C4—C3 | 119.7 (3) | C11—C12—H12 | 119.6 |
C5—C4—H4 | 120.2 | ||
C3—N1—N2—C7 | −178.9 (2) | C4—C5—C6—C1 | −0.3 (4) |
O2—S1—C1—C2 | 8.3 (3) | C2—C1—C6—C5 | 0.8 (4) |
O3—S1—C1—C2 | 130.0 (2) | S1—C1—C6—C5 | −177.2 (2) |
O1—S1—C1—C2 | −111.3 (2) | N1—N2—C7—C12 | 178.2 (2) |
O2—S1—C1—C6 | −173.6 (2) | N1—N2—C7—C8 | −0.8 (4) |
O3—S1—C1—C6 | −51.9 (2) | C12—C7—C8—C9 | 1.3 (4) |
O1—S1—C1—C6 | 66.7 (2) | N2—C7—C8—C9 | −179.7 (2) |
C6—C1—C2—C3 | −1.0 (4) | C7—C8—C9—C10 | −0.1 (4) |
S1—C1—C2—C3 | 177.0 (2) | C8—C9—C10—O4 | 179.3 (2) |
C1—C2—C3—C4 | 0.6 (4) | C8—C9—C10—C11 | −1.3 (4) |
C1—C2—C3—N1 | −179.6 (2) | O4—C10—C11—C12 | −179.2 (2) |
N2—N1—C3—C4 | −6.4 (4) | C9—C10—C11—C12 | 1.3 (4) |
N2—N1—C3—C2 | 173.9 (2) | C8—C7—C12—C11 | −1.3 (4) |
C2—C3—C4—C5 | −0.1 (4) | N2—C7—C12—C11 | 179.6 (2) |
N1—C3—C4—C5 | −179.8 (2) | C10—C11—C12—C7 | −0.1 (4) |
C3—C4—C5—C6 | −0.1 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H1N···O2i | 0.90 (4) | 2.48 (3) | 3.002 (4) | 118 (3) |
N3—H1N···O4ii | 0.90 (4) | 2.35 (3) | 2.913 (4) | 121 (3) |
N3—H1N···O4iii | 0.90 (4) | 2.50 (4) | 3.162 (4) | 131 (3) |
N3—H2N···O1 | 0.96 (4) | 1.94 (4) | 2.893 (3) | 171 (3) |
N3—H3N···O1iv | 0.89 (3) | 1.97 (3) | 2.822 (3) | 159 (3) |
N3—H4N···O3v | 0.90 (4) | 1.97 (4) | 2.831 (3) | 160 (3) |
O4—H1H···O2vi | 0.82 (4) | 2.00 (4) | 2.707 (3) | 144 (4) |
Symmetry codes: (i) x−1/2, −y+1, −z+1/2; (ii) x−1/2, y−1/2, −z; (iii) −x+2, y−1/2, −z+1/2; (iv) −x+3/2, y, z+1/2; (v) −x+3/2, y, z−1/2; (vi) −x+5/2, −y+3/2, z. |
[K(C12H9N2O4S)(H2O)] | Z = 4 |
Mr = 334.39 | F(000) = 688 |
Triclinic, P1 | Dx = 1.633 Mg m−3 |
a = 5.9620 (7) Å | Synchrotron radiation, λ = 0.689 Å |
b = 7.2033 (11) Å | Cell parameters from 10143 reflections |
c = 31.929 (5) Å | θ = 2.5–26.0° |
α = 83.852 (14)° | µ = 0.51 mm−1 |
β = 86.361 (15)° | T = 150 K |
γ = 88.868 (15)° | Plate, yellow |
V = 1360.5 (3) Å3 | 0.20 × 0.14 × 0.03 mm |
Bruker APEXII CCD diffractometer | 4405 reflections with I > 2σ(I) |
Radiation source: Daresbury SRS Station 9.8 | Rint = 0.032 |
ω scans | θmax = 26.0°, θmin = 2.5° |
Absorption correction: multi-scan (SADABS; Bruker, 2012) | h = −7→7 |
Tmin = 0.751, Tmax = 1.000 | k = −9→9 |
10143 measured reflections | l = −40→39 |
5691 independent reflections |
Refinement on F2 | 6 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.060 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.180 | w = 1/[σ2(Fo2) + (0.1366P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.001 |
5691 reflections | Δρmax = 0.59 e Å−3 |
403 parameters | Δρmin = −0.67 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
K1 | 0.36696 (11) | −0.01827 (9) | 0.75009 (2) | 0.02505 (19) | |
K2 | 1.04941 (11) | −0.53233 (10) | 0.77938 (2) | 0.02465 (19) | |
S1 | −0.11322 (12) | −0.24184 (10) | 0.69389 (2) | 0.01926 (19) | |
S2 | 0.54537 (12) | −0.32684 (11) | 0.83209 (2) | 0.0213 (2) | |
O1 | 0.0904 (4) | −0.2355 (3) | 0.71678 (6) | 0.0268 (5) | |
O2 | −0.2642 (4) | −0.0810 (3) | 0.69821 (6) | 0.0277 (5) | |
O3 | −0.2304 (4) | −0.4194 (3) | 0.70500 (7) | 0.0281 (5) | |
O4 | 0.5925 (4) | −0.2727 (3) | 0.32948 (6) | 0.0285 (5) | |
O5 | 0.6597 (4) | −0.4995 (3) | 0.82126 (7) | 0.0306 (5) | |
O6 | 0.6621 (4) | −0.1604 (4) | 0.81212 (7) | 0.0371 (6) | |
O7 | 0.3080 (4) | −0.3207 (3) | 0.82324 (6) | 0.0254 (5) | |
O8 | 0.9857 (4) | −0.0787 (3) | 1.18624 (6) | 0.0246 (5) | |
O1W | 0.9915 (4) | −0.7663 (3) | 0.70673 (7) | 0.0294 (5) | |
O2W | 1.4663 (4) | −0.6612 (3) | 0.75731 (7) | 0.0267 (5) | |
N1 | 0.1526 (4) | −0.2478 (4) | 0.51080 (8) | 0.0241 (6) | |
N2 | 0.3607 (4) | −0.2444 (4) | 0.50057 (8) | 0.0244 (6) | |
N3 | 0.6433 (4) | −0.2553 (3) | 1.01425 (7) | 0.0211 (5) | |
N4 | 0.8446 (4) | −0.2370 (3) | 1.02266 (8) | 0.0219 (5) | |
C1 | −0.0256 (5) | −0.2344 (4) | 0.63988 (8) | 0.0188 (6) | |
C2 | 0.1890 (5) | −0.3011 (4) | 0.62818 (9) | 0.0224 (6) | |
H2 | 0.289784 | −0.343168 | 0.649169 | 0.027* | |
C3 | 0.2539 (5) | −0.3054 (4) | 0.58561 (9) | 0.0229 (6) | |
H3 | 0.399776 | −0.348997 | 0.577331 | 0.027* | |
C4 | 0.1017 (5) | −0.2448 (4) | 0.55507 (9) | 0.0210 (6) | |
C5 | −0.1142 (5) | −0.1801 (5) | 0.56692 (9) | 0.0261 (7) | |
H5 | −0.216726 | −0.140838 | 0.546051 | 0.031* | |
C6 | −0.1768 (5) | −0.1740 (4) | 0.60948 (9) | 0.0221 (6) | |
H6 | −0.321876 | −0.128863 | 0.617822 | 0.027* | |
C7 | 0.4134 (5) | −0.2564 (4) | 0.45656 (9) | 0.0223 (6) | |
C8 | 0.6279 (5) | −0.2012 (4) | 0.44089 (9) | 0.0240 (6) | |
H8 | 0.731988 | −0.162898 | 0.459482 | 0.029* | |
C9 | 0.6902 (5) | −0.2017 (4) | 0.39842 (9) | 0.0223 (6) | |
H9 | 0.834366 | −0.158982 | 0.387603 | 0.027* | |
C10 | 0.5398 (5) | −0.2654 (4) | 0.37162 (9) | 0.0214 (6) | |
C11 | 0.3261 (5) | −0.3279 (5) | 0.38736 (9) | 0.0250 (6) | |
H11 | 0.225448 | −0.374106 | 0.369166 | 0.030* | |
C12 | 0.2637 (5) | −0.3213 (5) | 0.42974 (9) | 0.0251 (7) | |
H12 | 0.118444 | −0.361226 | 0.440581 | 0.030* | |
C13 | 0.5661 (5) | −0.3265 (4) | 0.88708 (9) | 0.0201 (6) | |
C14 | 0.3888 (5) | −0.2573 (4) | 0.91189 (9) | 0.0239 (6) | |
H14 | 0.250402 | −0.221333 | 0.899981 | 0.029* | |
C15 | 0.4177 (5) | −0.2415 (4) | 0.95442 (9) | 0.0227 (6) | |
H15 | 0.297484 | −0.197564 | 0.971870 | 0.027* | |
C16 | 0.6237 (5) | −0.2906 (4) | 0.97118 (9) | 0.0192 (6) | |
C17 | 0.7970 (5) | −0.3667 (4) | 0.94658 (9) | 0.0219 (6) | |
H17 | 0.934209 | −0.405492 | 0.958599 | 0.026* | |
C18 | 0.7675 (5) | −0.3852 (4) | 0.90454 (9) | 0.0235 (6) | |
H18 | 0.884138 | −0.437672 | 0.887653 | 0.028* | |
C19 | 0.8724 (5) | −0.2009 (4) | 1.06517 (8) | 0.0199 (6) | |
C20 | 1.0813 (5) | −0.1333 (4) | 1.07323 (9) | 0.0216 (6) | |
H20 | 1.196039 | −0.116093 | 1.051188 | 0.026* | |
C21 | 1.1211 (5) | −0.0912 (4) | 1.11342 (9) | 0.0214 (6) | |
H21 | 1.263161 | −0.044719 | 1.118899 | 0.026* | |
C22 | 0.9530 (5) | −0.1169 (4) | 1.14585 (9) | 0.0209 (6) | |
C23 | 0.7465 (5) | −0.1886 (4) | 1.13802 (9) | 0.0222 (6) | |
H23 | 0.633336 | −0.207817 | 1.160321 | 0.027* | |
C24 | 0.7039 (5) | −0.2324 (4) | 1.09797 (9) | 0.0214 (6) | |
H24 | 0.563378 | −0.282682 | 1.092802 | 0.026* | |
H4H | 0.736 (2) | −0.251 (5) | 0.3235 (11) | 0.025 (9)* | |
H8H | 1.121 (4) | −0.034 (7) | 1.1861 (17) | 0.075 (17)* | |
H1W | 0.909 (6) | −0.666 (3) | 0.7025 (12) | 0.040 (11)* | |
H2W | 0.908 (7) | −0.862 (5) | 0.7037 (16) | 0.060 (15)* | |
H3W | 1.510 (7) | −0.619 (6) | 0.7314 (6) | 0.043 (11)* | |
H4W | 1.541 (7) | −0.598 (6) | 0.7737 (12) | 0.051 (13)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
K1 | 0.0278 (4) | 0.0274 (4) | 0.0203 (3) | 0.0015 (3) | −0.0027 (3) | −0.0038 (3) |
K2 | 0.0222 (4) | 0.0303 (4) | 0.0206 (3) | 0.0020 (3) | −0.0018 (2) | 0.0010 (3) |
S1 | 0.0225 (4) | 0.0210 (4) | 0.0138 (3) | 0.0025 (3) | 0.0000 (3) | −0.0006 (3) |
S2 | 0.0225 (4) | 0.0284 (4) | 0.0133 (3) | −0.0015 (3) | −0.0034 (3) | −0.0025 (3) |
O1 | 0.0307 (12) | 0.0315 (12) | 0.0184 (10) | 0.0001 (9) | −0.0038 (8) | −0.0022 (9) |
O2 | 0.0298 (12) | 0.0324 (12) | 0.0202 (11) | 0.0116 (9) | 0.0018 (8) | −0.0032 (9) |
O3 | 0.0328 (12) | 0.0253 (12) | 0.0248 (11) | −0.0031 (9) | 0.0047 (9) | 0.0007 (9) |
O4 | 0.0298 (12) | 0.0408 (14) | 0.0146 (10) | 0.0061 (10) | −0.0013 (8) | −0.0032 (9) |
O5 | 0.0295 (12) | 0.0425 (14) | 0.0223 (11) | 0.0108 (10) | −0.0040 (9) | −0.0148 (10) |
O6 | 0.0503 (15) | 0.0400 (15) | 0.0209 (11) | −0.0217 (12) | −0.0086 (10) | 0.0043 (10) |
O7 | 0.0260 (11) | 0.0308 (12) | 0.0206 (10) | 0.0020 (9) | −0.0076 (8) | −0.0054 (9) |
O8 | 0.0288 (12) | 0.0326 (12) | 0.0127 (9) | −0.0007 (9) | −0.0031 (8) | −0.0034 (8) |
O1W | 0.0303 (13) | 0.0298 (13) | 0.0277 (12) | 0.0033 (10) | −0.0002 (9) | −0.0034 (10) |
O2W | 0.0299 (12) | 0.0301 (12) | 0.0201 (11) | −0.0065 (9) | 0.0039 (9) | −0.0046 (9) |
N1 | 0.0303 (14) | 0.0253 (14) | 0.0169 (12) | 0.0039 (10) | −0.0013 (10) | −0.0038 (10) |
N2 | 0.0268 (13) | 0.0285 (14) | 0.0173 (12) | 0.0021 (10) | 0.0004 (10) | −0.0011 (10) |
N3 | 0.0247 (13) | 0.0244 (13) | 0.0145 (11) | 0.0036 (10) | −0.0051 (9) | −0.0027 (9) |
N4 | 0.0292 (14) | 0.0206 (13) | 0.0162 (11) | 0.0042 (10) | −0.0030 (9) | −0.0037 (9) |
C1 | 0.0262 (15) | 0.0155 (13) | 0.0146 (13) | −0.0017 (11) | 0.0016 (10) | −0.0020 (10) |
C2 | 0.0247 (15) | 0.0246 (15) | 0.0174 (13) | 0.0030 (11) | −0.0010 (11) | −0.0007 (11) |
C3 | 0.0207 (14) | 0.0276 (16) | 0.0195 (14) | 0.0047 (11) | −0.0004 (11) | −0.0007 (11) |
C4 | 0.0218 (14) | 0.0246 (15) | 0.0163 (13) | 0.0020 (11) | −0.0007 (10) | −0.0014 (11) |
C5 | 0.0242 (15) | 0.0342 (18) | 0.0187 (14) | 0.0072 (12) | −0.0029 (11) | 0.0018 (12) |
C6 | 0.0190 (14) | 0.0270 (16) | 0.0200 (14) | 0.0043 (11) | −0.0036 (11) | −0.0004 (11) |
C7 | 0.0264 (15) | 0.0251 (15) | 0.0147 (13) | 0.0057 (11) | −0.0021 (11) | 0.0010 (11) |
C8 | 0.0267 (15) | 0.0255 (16) | 0.0210 (15) | 0.0001 (12) | −0.0020 (11) | −0.0080 (12) |
C9 | 0.0228 (14) | 0.0226 (15) | 0.0213 (14) | −0.0006 (11) | −0.0003 (11) | −0.0017 (11) |
C10 | 0.0247 (15) | 0.0240 (15) | 0.0149 (13) | 0.0057 (11) | −0.0025 (10) | 0.0005 (11) |
C11 | 0.0235 (15) | 0.0318 (17) | 0.0201 (14) | 0.0042 (12) | −0.0055 (11) | −0.0037 (12) |
C12 | 0.0216 (15) | 0.0320 (17) | 0.0207 (14) | 0.0034 (12) | −0.0008 (11) | −0.0001 (12) |
C13 | 0.0255 (15) | 0.0218 (14) | 0.0131 (12) | 0.0022 (11) | −0.0056 (10) | −0.0007 (10) |
C14 | 0.0230 (15) | 0.0292 (16) | 0.0189 (14) | 0.0035 (11) | −0.0007 (11) | −0.0005 (11) |
C15 | 0.0250 (15) | 0.0252 (16) | 0.0182 (13) | 0.0028 (11) | −0.0003 (11) | −0.0039 (11) |
C16 | 0.0233 (14) | 0.0170 (14) | 0.0172 (13) | −0.0010 (10) | −0.0024 (10) | 0.0004 (10) |
C17 | 0.0227 (14) | 0.0252 (15) | 0.0187 (14) | 0.0033 (11) | −0.0071 (11) | −0.0040 (11) |
C18 | 0.0240 (15) | 0.0307 (16) | 0.0161 (13) | 0.0067 (12) | −0.0029 (11) | −0.0040 (11) |
C19 | 0.0282 (15) | 0.0212 (14) | 0.0110 (12) | 0.0085 (11) | −0.0057 (10) | −0.0042 (10) |
C20 | 0.0164 (13) | 0.0290 (16) | 0.0192 (14) | −0.0004 (11) | −0.0012 (10) | −0.0019 (11) |
C21 | 0.0222 (14) | 0.0228 (15) | 0.0193 (14) | −0.0012 (11) | −0.0039 (11) | −0.0012 (11) |
C22 | 0.0274 (15) | 0.0201 (14) | 0.0148 (13) | 0.0041 (11) | −0.0040 (11) | 0.0012 (10) |
C23 | 0.0263 (15) | 0.0248 (15) | 0.0147 (13) | 0.0000 (11) | 0.0000 (11) | 0.0002 (11) |
C24 | 0.0201 (14) | 0.0225 (15) | 0.0213 (14) | 0.0001 (11) | −0.0044 (11) | 0.0009 (11) |
K1—O1 | 2.642 (2) | N3—N4 | 1.258 (4) |
K1—O2Wi | 2.688 (3) | N3—C16 | 1.437 (4) |
K1—O2ii | 2.728 (2) | N4—C19 | 1.429 (4) |
K1—O6 | 2.829 (3) | C1—C6 | 1.396 (4) |
K1—O8iii | 2.957 (2) | C1—C2 | 1.400 (4) |
K1—O7 | 3.027 (2) | C2—C3 | 1.393 (4) |
K1—O4iv | 3.116 (2) | C2—H2 | 0.9500 |
K1—O1Wi | 3.149 (2) | C3—C4 | 1.404 (4) |
K1—S2 | 3.4555 (11) | C3—H3 | 0.9500 |
K1—K2i | 4.1142 (12) | C4—C5 | 1.403 (4) |
K1—K2v | 4.1810 (12) | C5—C6 | 1.391 (4) |
K2—O5 | 2.625 (2) | C5—H5 | 0.9500 |
K2—O2W | 2.713 (2) | C6—H6 | 0.9500 |
K2—O7ii | 2.736 (2) | C7—C8 | 1.393 (4) |
K2—O1ii | 2.769 (2) | C7—C12 | 1.396 (4) |
K2—O8vi | 2.904 (2) | C8—C9 | 1.383 (4) |
K2—O3ii | 3.020 (2) | C8—H8 | 0.9500 |
K2—O1W | 3.050 (3) | C9—C10 | 1.395 (4) |
K2—C22vi | 3.285 (3) | C9—H9 | 0.9500 |
K2—C23vi | 3.414 (3) | C10—C11 | 1.404 (4) |
K2—S1ii | 3.4353 (11) | C11—C12 | 1.386 (4) |
K2—S2 | 3.7108 (11) | C11—H11 | 0.9500 |
K2—H1W | 2.91 (4) | C12—H12 | 0.9500 |
K2—H4W | 2.96 (4) | C13—C18 | 1.395 (4) |
S1—O1 | 1.460 (2) | C13—C14 | 1.397 (4) |
S1—O2 | 1.466 (2) | C14—C15 | 1.396 (4) |
S1—O3 | 1.469 (2) | C14—H14 | 0.9500 |
S1—C1 | 1.765 (3) | C15—C16 | 1.395 (4) |
S2—O7 | 1.460 (2) | C15—H15 | 0.9500 |
S2—O6 | 1.464 (2) | C16—C17 | 1.397 (4) |
S2—O5 | 1.470 (2) | C17—C18 | 1.385 (4) |
S2—C13 | 1.768 (3) | C17—H17 | 0.9500 |
O4—C10 | 1.368 (3) | C18—H18 | 0.9500 |
O4—H4H | 0.880 (10) | C19—C20 | 1.395 (4) |
O8—C22 | 1.374 (4) | C19—C24 | 1.408 (4) |
O8—H8H | 0.876 (11) | C20—C21 | 1.386 (4) |
O1W—H1W | 0.872 (10) | C20—H20 | 0.9500 |
O1W—H2W | 0.877 (10) | C21—C22 | 1.395 (4) |
O2W—H3W | 0.875 (10) | C21—H21 | 0.9500 |
O2W—H4W | 0.878 (10) | C22—C23 | 1.392 (4) |
N1—N2 | 1.262 (4) | C23—C24 | 1.389 (4) |
N1—C4 | 1.429 (4) | C23—H23 | 0.9500 |
N2—C7 | 1.432 (4) | C24—H24 | 0.9500 |
O1—K1—O2Wi | 143.99 (8) | S1ii—K2—H4W | 110.8 (9) |
O1—K1—O2ii | 96.82 (7) | S2—K2—H4W | 149.6 (4) |
O2Wi—K1—O2ii | 94.96 (7) | K1vii—K2—H4W | 54.5 (6) |
O1—K1—O6 | 122.07 (7) | H1W—K2—H4W | 102.9 (8) |
O2Wi—K1—O6 | 93.29 (8) | O1—S1—O2 | 113.45 (14) |
O2ii—K1—O6 | 81.29 (7) | O1—S1—O3 | 111.38 (13) |
O1—K1—O8iii | 91.74 (7) | O2—S1—O3 | 111.79 (13) |
O2Wi—K1—O8iii | 78.80 (7) | O1—S1—C1 | 106.56 (13) |
O2ii—K1—O8iii | 171.32 (7) | O2—S1—C1 | 106.74 (13) |
O6—K1—O8iii | 92.97 (7) | O3—S1—C1 | 106.42 (13) |
O1—K1—O7 | 81.20 (7) | O1—S1—K2v | 51.36 (9) |
O2Wi—K1—O7 | 124.81 (7) | O2—S1—K2v | 122.43 (9) |
O2ii—K1—O7 | 112.15 (7) | O3—S1—K2v | 61.34 (10) |
O6—K1—O7 | 48.56 (6) | C1—S1—K2v | 130.60 (10) |
O8iii—K1—O7 | 67.71 (6) | O7—S2—O6 | 111.40 (15) |
O1—K1—O4iv | 94.29 (7) | O7—S2—O5 | 112.83 (14) |
O2Wi—K1—O4iv | 59.54 (7) | O6—S2—O5 | 111.82 (15) |
O2ii—K1—O4iv | 67.50 (6) | O7—S2—C13 | 108.58 (13) |
O6—K1—O4iv | 134.83 (7) | O6—S2—C13 | 106.38 (14) |
O8iii—K1—O4iv | 113.39 (6) | O5—S2—C13 | 105.38 (13) |
O7—K1—O4iv | 175.43 (7) | O7—S2—K1 | 60.88 (9) |
O1—K1—O1Wi | 71.39 (7) | O6—S2—K1 | 53.06 (10) |
O2Wi—K1—O1Wi | 72.75 (7) | O5—S2—K1 | 117.59 (9) |
O2ii—K1—O1Wi | 114.51 (7) | C13—S2—K1 | 136.61 (10) |
O6—K1—O1Wi | 159.23 (7) | O7—S2—K2 | 132.58 (9) |
O8iii—K1—O1Wi | 69.63 (6) | O6—S2—K2 | 77.99 (12) |
O7—K1—O1Wi | 127.79 (6) | O5—S2—K2 | 34.05 (10) |
O4iv—K1—O1Wi | 50.58 (6) | C13—S2—K2 | 112.84 (10) |
O1—K1—S2 | 99.79 (5) | K1—S2—K2 | 100.28 (2) |
O2Wi—K1—S2 | 113.31 (6) | S1—O1—K1 | 145.40 (14) |
O2ii—K1—S2 | 93.51 (5) | S1—O1—K2v | 104.32 (11) |
O6—K1—S2 | 24.42 (5) | K1—O1—K2v | 101.16 (7) |
O8iii—K1—S2 | 83.59 (5) | S1—O2—K1v | 133.87 (12) |
O7—K1—S2 | 24.92 (4) | S1—O3—K2v | 93.40 (11) |
O4iv—K1—S2 | 157.67 (5) | C10—O4—K1iv | 135.45 (18) |
O1Wi—K1—S2 | 151.14 (5) | C10—O4—H4H | 110 (2) |
O1—K1—K2i | 111.21 (5) | K1iv—O4—H4H | 72 (2) |
O2Wi—K1—K2i | 40.61 (5) | S2—O5—K2 | 127.68 (14) |
O2ii—K1—K2i | 131.67 (5) | S2—O6—K1 | 102.52 (12) |
O6—K1—K2i | 112.19 (6) | S2—O7—K2v | 133.41 (13) |
O8iii—K1—K2i | 44.90 (5) | S2—O7—K1 | 94.20 (10) |
O7—K1—K2i | 110.51 (5) | K2v—O7—K1 | 92.89 (6) |
O4iv—K1—K2i | 71.74 (5) | C22—O8—K2vi | 93.35 (16) |
O1Wi—K1—K2i | 47.40 (5) | C22—O8—K1iii | 126.30 (17) |
S2—K1—K2i | 118.03 (2) | K2vi—O8—K1iii | 89.15 (6) |
O1—K1—K2v | 40.53 (5) | C22—O8—H8H | 107 (4) |
O2Wi—K1—K2v | 157.68 (5) | K2vi—O8—H8H | 114 (4) |
O2ii—K1—K2v | 106.51 (6) | K1iii—O8—H8H | 120 (4) |
O6—K1—K2v | 84.18 (5) | K2—O1W—K1vii | 83.14 (6) |
O8iii—K1—K2v | 79.19 (5) | K2—O1W—H1W | 72 (3) |
O7—K1—K2v | 40.81 (4) | K1vii—O1W—H1W | 155 (3) |
O4iv—K1—K2v | 134.64 (5) | K2—O1W—H2W | 134 (3) |
O1Wi—K1—K2v | 102.80 (5) | K1vii—O1W—H2W | 93 (3) |
S2—K1—K2v | 60.30 (2) | H1W—O1W—H2W | 108 (4) |
K2i—K1—K2v | 120.54 (2) | K1vii—O2W—K2 | 99.23 (7) |
O5—K2—O2W | 160.56 (7) | K1vii—O2W—H3W | 103 (3) |
O5—K2—O7ii | 99.88 (7) | K2—O2W—H3W | 112 (3) |
O2W—K2—O7ii | 79.33 (7) | K1vii—O2W—H4W | 139 (3) |
O5—K2—O1ii | 108.12 (7) | K2—O2W—H4W | 97 (3) |
O2W—K2—O1ii | 91.20 (7) | H3W—O2W—H4W | 106 (4) |
O7ii—K2—O1ii | 84.47 (7) | N2—N1—C4 | 113.4 (3) |
O5—K2—O8vi | 83.48 (7) | N1—N2—C7 | 113.7 (3) |
O2W—K2—O8vi | 79.34 (7) | N4—N3—C16 | 112.2 (2) |
O7ii—K2—O8vi | 114.54 (7) | N3—N4—C19 | 114.2 (2) |
O1ii—K2—O8vi | 156.28 (7) | C6—C1—C2 | 121.0 (3) |
O5—K2—O3ii | 81.94 (7) | C6—C1—S1 | 119.4 (2) |
O2W—K2—O3ii | 113.62 (7) | C2—C1—S1 | 119.5 (2) |
O7ii—K2—O3ii | 130.17 (7) | C3—C2—C1 | 119.7 (3) |
O1ii—K2—O3ii | 49.17 (6) | C3—C2—H2 | 120.2 |
O8vi—K2—O3ii | 115.13 (7) | C1—C2—H2 | 120.2 |
O5—K2—O1W | 109.02 (7) | C2—C3—C4 | 119.4 (3) |
O2W—K2—O1W | 74.07 (7) | C2—C3—H3 | 120.3 |
O7ii—K2—O1W | 151.04 (7) | C4—C3—H3 | 120.3 |
O1ii—K2—O1W | 84.82 (7) | C5—C4—C3 | 120.8 (3) |
O8vi—K2—O1W | 71.71 (6) | C5—C4—N1 | 116.1 (3) |
O3ii—K2—O1W | 54.96 (6) | C3—C4—N1 | 123.1 (3) |
O5—K2—C22vi | 75.97 (8) | C6—C5—C4 | 119.5 (3) |
O2W—K2—C22vi | 84.63 (7) | C6—C5—H5 | 120.3 |
O7ii—K2—C22vi | 92.32 (7) | C4—C5—H5 | 120.3 |
O1ii—K2—C22vi | 175.16 (7) | C5—C6—C1 | 119.7 (3) |
O8vi—K2—C22vi | 24.68 (7) | C5—C6—H6 | 120.1 |
O3ii—K2—C22vi | 135.03 (7) | C1—C6—H6 | 120.1 |
O1W—K2—C22vi | 96.36 (7) | C8—C7—C12 | 120.0 (3) |
O5—K2—C23vi | 91.18 (7) | C8—C7—N2 | 116.5 (3) |
O2W—K2—C23vi | 70.03 (7) | C12—C7—N2 | 123.5 (3) |
O7ii—K2—C23vi | 71.42 (7) | C9—C8—C7 | 120.4 (3) |
O1ii—K2—C23vi | 151.52 (7) | C9—C8—H8 | 119.8 |
O8vi—K2—C23vi | 43.13 (7) | C7—C8—H8 | 119.8 |
O3ii—K2—C23vi | 158.09 (7) | C8—C9—C10 | 119.5 (3) |
O1W—K2—C23vi | 109.00 (7) | C8—C9—H9 | 120.3 |
C22vi—K2—C23vi | 23.89 (7) | C10—C9—H9 | 120.3 |
O5—K2—S1ii | 92.88 (6) | O4—C10—C9 | 122.4 (3) |
O2W—K2—S1ii | 106.08 (5) | O4—C10—C11 | 117.1 (3) |
O7ii—K2—S1ii | 105.92 (5) | C9—C10—C11 | 120.6 (3) |
O1ii—K2—S1ii | 24.32 (5) | C12—C11—C10 | 119.3 (3) |
O8vi—K2—S1ii | 139.42 (5) | C12—C11—H11 | 120.4 |
O3ii—K2—S1ii | 25.26 (4) | C10—C11—H11 | 120.4 |
O1W—K2—S1ii | 71.45 (5) | C11—C12—C7 | 120.2 (3) |
C22vi—K2—S1ii | 160.14 (6) | C11—C12—H12 | 119.9 |
C23vi—K2—S1ii | 175.50 (5) | C7—C12—H12 | 119.9 |
O5—K2—S2 | 18.27 (6) | C18—C13—C14 | 120.9 (3) |
O2W—K2—S2 | 166.25 (6) | C18—C13—S2 | 118.7 (2) |
O7ii—K2—S2 | 88.14 (5) | C14—C13—S2 | 120.3 (2) |
O1ii—K2—S2 | 93.22 (5) | C15—C14—C13 | 119.1 (3) |
O8vi—K2—S2 | 101.09 (5) | C15—C14—H14 | 120.4 |
O3ii—K2—S2 | 78.85 (4) | C13—C14—H14 | 120.4 |
O1W—K2—S2 | 119.29 (5) | C16—C15—C14 | 119.8 (3) |
C22vi—K2—S2 | 90.29 (5) | C16—C15—H15 | 120.1 |
C23vi—K2—S2 | 100.72 (5) | C14—C15—H15 | 120.1 |
S1ii—K2—S2 | 82.67 (2) | C15—C16—C17 | 120.7 (3) |
O5—K2—K1vii | 127.22 (6) | C15—C16—N3 | 115.7 (2) |
O2W—K2—K1vii | 40.16 (5) | C17—C16—N3 | 123.6 (3) |
O7ii—K2—K1vii | 112.89 (5) | C18—C17—C16 | 119.6 (3) |
O1ii—K2—K1vii | 114.97 (5) | C18—C17—H17 | 120.2 |
O8vi—K2—K1vii | 45.95 (4) | C16—C17—H17 | 120.2 |
O3ii—K2—K1vii | 104.05 (5) | C17—C18—C13 | 119.8 (3) |
O1W—K2—K1vii | 49.46 (5) | C17—C18—H18 | 120.1 |
C22vi—K2—K1vii | 62.99 (5) | C13—C18—H18 | 120.1 |
C23vi—K2—K1vii | 63.93 (5) | C20—C19—C24 | 120.4 (3) |
S1ii—K2—K1vii | 114.76 (2) | C20—C19—N4 | 116.1 (2) |
S2—K2—K1vii | 145.49 (3) | C24—C19—N4 | 123.5 (3) |
O5—K2—H1W | 100.8 (7) | C21—C20—C19 | 119.9 (3) |
O2W—K2—H1W | 86.6 (5) | C21—C20—H20 | 120.0 |
O7ii—K2—H1W | 153.4 (8) | C19—C20—H20 | 120.0 |
O1ii—K2—H1W | 73.3 (6) | C20—C21—C22 | 120.1 (3) |
O8vi—K2—H1W | 84.4 (5) | C20—C21—H21 | 119.9 |
O3ii—K2—H1W | 38.4 (2) | C22—C21—H21 | 119.9 |
O1W—K2—H1W | 16.6 (2) | O8—C22—C23 | 117.9 (2) |
C22vi—K2—H1W | 108.8 (6) | O8—C22—C21 | 122.1 (3) |
C23vi—K2—H1W | 124.5 (4) | C23—C22—C21 | 119.9 (3) |
S1ii—K2—H1W | 56.5 (4) | O8—C22—K2vi | 61.97 (14) |
S2—K2—H1W | 107.2 (5) | C23—C22—K2vi | 83.25 (17) |
K1vii—K2—H1W | 66.0 (2) | C21—C22—K2vi | 123.43 (19) |
O5—K2—H4W | 153.1 (7) | C24—C23—C22 | 120.7 (3) |
O2W—K2—H4W | 17.1 (4) | C24—C23—K2vi | 129.2 (2) |
O7ii—K2—H4W | 62.3 (4) | C22—C23—K2vi | 72.86 (16) |
O1ii—K2—H4W | 90.9 (9) | C24—C23—H23 | 119.6 |
O8vi—K2—H4W | 86.3 (8) | C22—C23—H23 | 119.6 |
O3ii—K2—H4W | 124.8 (7) | K2vi—C23—H23 | 70.0 |
O1W—K2—H4W | 91.1 (4) | C23—C24—C19 | 118.9 (3) |
C22vi—K2—H4W | 84.4 (9) | C23—C24—H24 | 120.6 |
C23vi—K2—H4W | 64.8 (9) | C19—C24—H24 | 120.6 |
O2—S1—O1—K1 | −22.5 (2) | N2—C7—C8—C9 | −177.6 (3) |
O3—S1—O1—K1 | −149.71 (19) | C7—C8—C9—C10 | −2.7 (5) |
C1—S1—O1—K1 | 94.6 (2) | K1iv—O4—C10—C9 | −75.6 (4) |
K2v—S1—O1—K1 | −136.2 (2) | K1iv—O4—C10—C11 | 105.2 (3) |
O2—S1—O1—K2v | 113.68 (12) | C8—C9—C10—O4 | −178.8 (3) |
O3—S1—O1—K2v | −13.50 (14) | C8—C9—C10—C11 | 0.3 (4) |
C1—S1—O1—K2v | −129.16 (11) | O4—C10—C11—C12 | −179.3 (3) |
O1—S1—O2—K1v | −95.7 (2) | C9—C10—C11—C12 | 1.6 (4) |
O3—S1—O2—K1v | 31.2 (2) | C10—C11—C12—C7 | −1.1 (5) |
C1—S1—O2—K1v | 147.23 (17) | C8—C7—C12—C11 | −1.2 (5) |
K2v—S1—O2—K1v | −37.8 (2) | N2—C7—C12—C11 | 179.6 (3) |
O1—S1—O3—K2v | 11.99 (12) | O7—S2—C13—C18 | 161.7 (2) |
O2—S1—O3—K2v | −116.08 (11) | O6—S2—C13—C18 | −78.3 (3) |
C1—S1—O3—K2v | 127.74 (11) | O5—S2—C13—C18 | 40.6 (3) |
O7—S2—O5—K2 | 133.50 (15) | K1—S2—C13—C18 | −131.3 (2) |
O6—S2—O5—K2 | 7.0 (2) | K2—S2—C13—C18 | 5.3 (3) |
C13—S2—O5—K2 | −108.19 (16) | O7—S2—C13—C14 | −22.4 (3) |
K1—S2—O5—K2 | 65.57 (17) | O6—S2—C13—C14 | 97.6 (3) |
O7—S2—O6—K1 | −18.44 (16) | O5—S2—C13—C14 | −143.5 (3) |
O5—S2—O6—K1 | 108.85 (13) | K1—S2—C13—C14 | 44.6 (3) |
C13—S2—O6—K1 | −136.60 (12) | K2—S2—C13—C14 | −178.8 (2) |
K2—S2—O6—K1 | 112.84 (9) | C18—C13—C14—C15 | 2.0 (5) |
O6—S2—O7—K2v | 114.81 (18) | S2—C13—C14—C15 | −173.8 (2) |
O5—S2—O7—K2v | −11.9 (2) | C13—C14—C15—C16 | 1.6 (4) |
C13—S2—O7—K2v | −128.36 (16) | C14—C15—C16—C17 | −4.2 (4) |
K1—S2—O7—K2v | 97.99 (15) | C14—C15—C16—N3 | 175.1 (3) |
K2—S2—O7—K2v | 21.6 (2) | N4—N3—C16—C15 | −155.9 (3) |
O6—S2—O7—K1 | 16.82 (14) | N4—N3—C16—C17 | 23.3 (4) |
O5—S2—O7—K1 | −109.92 (12) | C15—C16—C17—C18 | 3.1 (4) |
C13—S2—O7—K1 | 133.65 (11) | N3—C16—C17—C18 | −176.1 (3) |
K2—S2—O7—K1 | −76.44 (11) | C16—C17—C18—C13 | 0.5 (5) |
C4—N1—N2—C7 | 177.2 (2) | C14—C13—C18—C17 | −3.1 (5) |
C16—N3—N4—C19 | 179.8 (2) | S2—C13—C18—C17 | 172.8 (2) |
O1—S1—C1—C6 | −157.8 (2) | N3—N4—C19—C20 | −164.3 (3) |
O2—S1—C1—C6 | −36.3 (3) | N3—N4—C19—C24 | 16.5 (4) |
O3—S1—C1—C6 | 83.2 (3) | C24—C19—C20—C21 | −2.0 (4) |
K2v—S1—C1—C6 | 149.3 (2) | N4—C19—C20—C21 | 178.8 (3) |
O1—S1—C1—C2 | 26.5 (3) | C19—C20—C21—C22 | 0.2 (4) |
O2—S1—C1—C2 | 148.1 (2) | K2vi—O8—C22—C23 | 64.3 (3) |
O3—S1—C1—C2 | −92.4 (3) | K1iii—O8—C22—C23 | −27.1 (4) |
K2v—S1—C1—C2 | −26.4 (3) | K2vi—O8—C22—C21 | −113.8 (3) |
C6—C1—C2—C3 | 0.7 (5) | K1iii—O8—C22—C21 | 154.8 (2) |
S1—C1—C2—C3 | 176.3 (2) | K1iii—O8—C22—K2vi | −91.41 (16) |
C1—C2—C3—C4 | −0.8 (5) | C20—C21—C22—O8 | 179.4 (3) |
C2—C3—C4—C5 | 0.0 (5) | C20—C21—C22—C23 | 1.3 (4) |
C2—C3—C4—N1 | −178.8 (3) | C20—C21—C22—K2vi | 103.9 (3) |
N2—N1—C4—C5 | 157.3 (3) | O8—C22—C23—C24 | −179.2 (3) |
N2—N1—C4—C3 | −23.8 (4) | C21—C22—C23—C24 | −1.0 (4) |
C3—C4—C5—C6 | 0.8 (5) | K2vi—C22—C23—C24 | −125.9 (3) |
N1—C4—C5—C6 | 179.7 (3) | O8—C22—C23—K2vi | −53.2 (2) |
C4—C5—C6—C1 | −0.8 (5) | C21—C22—C23—K2vi | 124.9 (3) |
C2—C1—C6—C5 | 0.1 (5) | C22—C23—C24—C19 | −0.7 (4) |
S1—C1—C6—C5 | −175.5 (2) | K2vi—C23—C24—C19 | −93.2 (3) |
N1—N2—C7—C8 | 162.4 (3) | C20—C19—C24—C23 | 2.3 (4) |
N1—N2—C7—C12 | −18.4 (4) | N4—C19—C24—C23 | −178.5 (3) |
C12—C7—C8—C9 | 3.1 (5) |
Symmetry codes: (i) x−1, y+1, z; (ii) x+1, y, z; (iii) −x+1, −y, −z+2; (iv) −x+1, −y, −z+1; (v) x−1, y, z; (vi) −x+2, −y−1, −z+2; (vii) x+1, y−1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4H···O1Wviii | 0.88 (1) | 1.83 (2) | 2.676 (3) | 160 (3) |
O8—H8H···O6ix | 0.88 (1) | 1.93 (3) | 2.748 (3) | 155 (5) |
O1W—H1W···O3ii | 0.87 (1) | 1.95 (2) | 2.801 (3) | 165 (4) |
O1W—H2W···O2vii | 0.88 (1) | 1.93 (1) | 2.803 (4) | 177 (5) |
O2W—H3W···O3x | 0.88 (1) | 2.20 (3) | 2.866 (3) | 133 (4) |
O2W—H3W···O4viii | 0.88 (1) | 2.29 (3) | 2.905 (3) | 127 (3) |
O2W—H4W···O5ii | 0.88 (1) | 1.92 (2) | 2.778 (3) | 165 (4) |
Symmetry codes: (ii) x+1, y, z; (vii) x+1, y−1, z; (viii) −x+2, −y−1, −z+1; (ix) −x+2, −y, −z+2; (x) x+2, y, z. |
[K(C12H10N3O3S)(H2O)2] | Z = 8 |
Mr = 351.42 | F(000) = 1456 |
Triclinic, P1 | Dx = 1.591 Mg m−3 |
a = 13.3058 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 13.6247 (2) Å | Cell parameters from 13626 reflections |
c = 18.4664 (3) Å | θ = 0.4–27.5° |
α = 88.373 (1)° | µ = 0.53 mm−1 |
β = 73.971 (1)° | T = 123 K |
γ = 66.313 (1)° | Sheet, yellow |
V = 2933.52 (8) Å3 | 0.7 × 0.3 × 0.02 mm |
Enraf–Nonius KappaCCD diffractometer | Rint = 0.023 |
Radiation source: sealed tube | θmax = 27.5°, θmin = 1.6° |
ω and phi scans | h = −17→17 |
26000 measured reflections | k = −17→17 |
13392 independent reflections | l = −23→23 |
10848 reflections with I > 2σ(I) |
Refinement on F2 | 24 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.036 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.098 | w = 1/[σ2(Fo2) + (0.0423P)2 + 2.5026P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
13392 reflections | Δρmax = 0.80 e Å−3 |
895 parameters | Δρmin = −0.79 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
K1 | 0.36432 (3) | 0.16149 (3) | 0.04727 (2) | 0.01821 (9) | |
K2 | 0.56585 (4) | 0.34009 (3) | 0.00078 (2) | 0.02089 (10) | |
K3 | 0.91040 (4) | 0.14309 (4) | 0.03328 (3) | 0.03042 (11) | |
K4 | 1.11003 (4) | 0.34080 (3) | −0.05349 (2) | 0.02172 (10) | |
S1 | 0.60885 (4) | 0.15844 (4) | 0.13423 (2) | 0.01617 (10) | |
S1A | 0.58680 (4) | 0.12938 (4) | −0.11362 (2) | 0.01558 (10) | |
S1B | 0.90352 (4) | 0.37392 (4) | 0.11946 (2) | 0.01655 (10) | |
S1C | 0.88336 (4) | 0.33155 (4) | −0.12057 (2) | 0.01540 (10) | |
O1 | 0.66126 (12) | 0.04249 (11) | 0.14108 (8) | 0.0230 (3) | |
O1A | 0.56604 (12) | 0.04564 (11) | −0.07064 (7) | 0.0224 (3) | |
O1B | 0.99145 (14) | 0.26429 (11) | 0.09571 (8) | 0.0291 (3) | |
O2 | 0.50128 (12) | 0.19267 (11) | 0.11594 (8) | 0.0235 (3) | |
O1W | 0.17161 (13) | 0.17402 (12) | 0.16143 (8) | 0.0256 (3) | |
O2A | 0.49160 (12) | 0.23543 (11) | −0.08722 (8) | 0.0234 (3) | |
O2B | 0.93443 (13) | 0.45183 (11) | 0.07491 (8) | 0.0268 (3) | |
O3 | 0.68945 (12) | 0.19462 (11) | 0.08320 (7) | 0.0225 (3) | |
O2W | 0.38778 (13) | 0.44516 (13) | 0.13668 (9) | 0.0281 (3) | |
O3A | 0.69498 (12) | 0.13426 (13) | −0.11593 (8) | 0.0279 (3) | |
O3B | 0.79182 (13) | 0.37860 (15) | 0.12144 (9) | 0.0365 (4) | |
O3W | 0.60988 (13) | 0.50992 (12) | 0.05734 (8) | 0.0257 (3) | |
O4W | 0.90005 (13) | −0.02527 (12) | 0.13023 (9) | 0.0282 (3) | |
O5W | 1.12711 (13) | −0.00124 (12) | 0.05792 (9) | 0.0293 (3) | |
H9W | 1.1620 (18) | −0.0209 (19) | 0.0100 (6) | 0.035* | |
H10W | 1.1896 (14) | −0.0422 (17) | 0.0707 (12) | 0.035* | |
O6W | 1.22994 (13) | 0.13309 (11) | −0.03169 (8) | 0.0233 (3) | |
O7W | 1.24230 (13) | 0.37602 (11) | 0.03183 (8) | 0.0255 (3) | |
O8W | 1.31574 (13) | 0.33491 (12) | −0.15548 (9) | 0.0275 (3) | |
H15W | 1.3758 (15) | 0.3093 (17) | −0.1379 (13) | 0.033* | |
H16W | 1.324 (2) | 0.3912 (13) | −0.1745 (13) | 0.033* | |
O1C | 0.76263 (16) | 0.35833 (19) | −0.08326 (10) | 0.0220 (4) | 0.878 (4) |
O2C | 0.91077 (19) | 0.42551 (14) | −0.12630 (9) | 0.0228 (4) | 0.878 (4) |
O3C | 0.95984 (17) | 0.24694 (16) | −0.08543 (11) | 0.0239 (4) | 0.878 (4) |
O4C | 0.7885 (13) | 0.3113 (13) | −0.0773 (8) | 0.0220 (4) | 0.122 (4) |
O5C | 0.8522 (14) | 0.4454 (11) | −0.1293 (7) | 0.0228 (4) | 0.122 (4) |
O6C | 0.9823 (14) | 0.2762 (13) | −0.1002 (9) | 0.0239 (4) | 0.122 (4) |
N1 | 0.49955 (13) | 0.33938 (12) | 0.44977 (9) | 0.0172 (3) | |
N1A | 0.62709 (13) | 0.03685 (12) | −0.43692 (9) | 0.0173 (3) | |
N1B | 0.87099 (13) | 0.46335 (12) | 0.44147 (9) | 0.0176 (3) | |
N1C | 1.00015 (13) | 0.16488 (12) | −0.44137 (9) | 0.0168 (3) | |
N2 | 0.58070 (13) | 0.34190 (12) | 0.47114 (9) | 0.0171 (3) | |
N2A | 0.63343 (13) | −0.05449 (12) | −0.45571 (9) | 0.0176 (3) | |
N2B | 0.86504 (13) | 0.55398 (12) | 0.46122 (9) | 0.0173 (3) | |
N2C | 0.92154 (13) | 0.15932 (12) | −0.46417 (9) | 0.0174 (3) | |
N3 | 0.46770 (17) | 0.50272 (14) | 0.77320 (9) | 0.0212 (3) | |
N3A | 0.69006 (15) | −0.15131 (16) | −0.76079 (10) | 0.0226 (4) | |
N3B | 0.81564 (15) | 0.63159 (16) | 0.76852 (10) | 0.0238 (4) | |
N3C | 1.04330 (17) | 0.00391 (14) | −0.76838 (9) | 0.0221 (4) | |
C1 | 0.57751 (15) | 0.21914 (14) | 0.22572 (10) | 0.0147 (3) | |
C1A | 0.59373 (15) | 0.10016 (14) | −0.20806 (10) | 0.0146 (3) | |
C1B | 0.89745 (15) | 0.40302 (14) | 0.21380 (10) | 0.0152 (3) | |
C1C | 0.91372 (15) | 0.27882 (14) | −0.21423 (10) | 0.0149 (3) | |
C2 | 0.46687 (16) | 0.25495 (14) | 0.27370 (10) | 0.0174 (4) | |
H2 | 0.406898 | 0.252756 | 0.256284 | 0.021* | |
C2A | 0.59565 (16) | 0.00262 (15) | −0.23074 (10) | 0.0173 (4) | |
H2A | 0.589860 | −0.047690 | −0.194892 | 0.021* | |
C2B | 0.89368 (16) | 0.50142 (15) | 0.23675 (10) | 0.0174 (4) | |
H2B | 0.897118 | 0.552580 | 0.201182 | 0.021* | |
C2C | 0.82832 (15) | 0.27106 (14) | −0.24037 (10) | 0.0166 (4) | |
H2C | 0.753033 | 0.291570 | −0.207218 | 0.020* | |
C3 | 0.44475 (16) | 0.29419 (15) | 0.34773 (11) | 0.0184 (4) | |
H3 | 0.369302 | 0.318596 | 0.381298 | 0.022* | |
C3A | 0.60606 (15) | −0.02100 (15) | −0.30590 (10) | 0.0169 (4) | |
H3A | 0.607199 | −0.087354 | −0.321551 | 0.020* | |
C3B | 0.88492 (15) | 0.52458 (15) | 0.31145 (10) | 0.0169 (4) | |
H3B | 0.882456 | 0.591479 | 0.327216 | 0.020* | |
C3C | 0.85370 (16) | 0.23313 (14) | −0.31523 (10) | 0.0166 (4) | |
H3C | 0.796056 | 0.226894 | −0.333317 | 0.020* | |
C4 | 0.53297 (16) | 0.29782 (14) | 0.37283 (10) | 0.0156 (4) | |
C4A | 0.61481 (15) | 0.05321 (14) | −0.35826 (10) | 0.0158 (4) | |
C4B | 0.87976 (15) | 0.44910 (15) | 0.36324 (10) | 0.0162 (4) | |
C4C | 0.96408 (15) | 0.20436 (14) | −0.36353 (10) | 0.0154 (3) | |
C5 | 0.64367 (15) | 0.26369 (14) | 0.32360 (10) | 0.0168 (4) | |
H5 | 0.703310 | 0.267634 | 0.340529 | 0.020* | |
C5A | 0.61020 (16) | 0.15177 (15) | −0.33499 (10) | 0.0179 (4) | |
H5A | 0.614125 | 0.202845 | −0.370557 | 0.022* | |
C5B | 0.88510 (16) | 0.35028 (15) | 0.34002 (10) | 0.0179 (4) | |
H5B | 0.882686 | 0.298779 | 0.375479 | 0.022* | |
C5C | 1.04950 (16) | 0.21144 (15) | −0.33698 (10) | 0.0179 (4) | |
H5C | 1.124708 | 0.191197 | −0.370185 | 0.022* | |
C6 | 0.66621 (16) | 0.22407 (15) | 0.24999 (11) | 0.0180 (4) | |
H6 | 0.741426 | 0.200389 | 0.216181 | 0.022* | |
C6A | 0.59988 (16) | 0.17544 (14) | −0.25996 (10) | 0.0167 (4) | |
H6A | 0.597033 | 0.242455 | −0.244075 | 0.020* | |
C6B | 0.89394 (16) | 0.32676 (15) | 0.26520 (10) | 0.0176 (4) | |
H6B | 0.897544 | 0.259428 | 0.249272 | 0.021* | |
C6C | 1.02495 (16) | 0.24797 (15) | −0.26216 (10) | 0.0173 (4) | |
H6C | 1.083268 | 0.251967 | −0.243697 | 0.021* | |
C7 | 0.54673 (16) | 0.38451 (14) | 0.54765 (10) | 0.0157 (4) | |
C7A | 0.64460 (15) | −0.07259 (14) | −0.53316 (10) | 0.0158 (4) | |
C7B | 0.85779 (15) | 0.56769 (15) | 0.53871 (10) | 0.0162 (4) | |
C7C | 0.95806 (16) | 0.11810 (14) | −0.54119 (10) | 0.0155 (4) | |
C8 | 0.43404 (16) | 0.42187 (15) | 0.59522 (10) | 0.0173 (4) | |
H8 | 0.374791 | 0.420291 | 0.576679 | 0.021* | |
C8A | 0.65069 (15) | −0.17206 (15) | −0.55619 (11) | 0.0178 (4) | |
H8A | 0.646107 | −0.222375 | −0.520123 | 0.021* | |
C8B | 0.84642 (16) | 0.66756 (15) | 0.56518 (11) | 0.0182 (4) | |
H8B | 0.846841 | 0.721222 | 0.531250 | 0.022* | |
C8C | 0.87466 (16) | 0.11037 (15) | −0.56976 (10) | 0.0177 (4) | |
H8C | 0.798442 | 0.131704 | −0.537895 | 0.021* | |
C9 | 0.40933 (16) | 0.46096 (15) | 0.66906 (11) | 0.0186 (4) | |
H9 | 0.332944 | 0.485441 | 0.701215 | 0.022* | |
C9A | 0.66334 (16) | −0.19812 (15) | −0.63115 (11) | 0.0180 (4) | |
H9A | 0.667436 | −0.266082 | −0.646125 | 0.022* | |
C9B | 0.83449 (16) | 0.68896 (15) | 0.64097 (11) | 0.0190 (4) | |
H9B | 0.826049 | 0.757445 | 0.658631 | 0.023* | |
C9C | 0.90248 (16) | 0.07160 (15) | −0.64467 (11) | 0.0185 (4) | |
H9C | 0.845055 | 0.066993 | −0.663857 | 0.022* | |
C10 | 0.49517 (16) | 0.46511 (14) | 0.69734 (10) | 0.0168 (4) | |
C10A | 0.67011 (15) | −0.12459 (15) | −0.68493 (10) | 0.0175 (4) | |
C10B | 0.83482 (15) | 0.61027 (15) | 0.69145 (10) | 0.0177 (4) | |
C10C | 1.01397 (16) | 0.03949 (14) | −0.69172 (10) | 0.0167 (4) | |
C11 | 0.60659 (16) | 0.42965 (15) | 0.64948 (11) | 0.0181 (4) | |
H11 | 0.665465 | 0.432619 | 0.667803 | 0.022* | |
C11A | 0.66057 (16) | −0.02318 (15) | −0.66082 (11) | 0.0197 (4) | |
H11A | 0.663013 | 0.028064 | −0.696478 | 0.024* | |
C11B | 0.85061 (16) | 0.50880 (15) | 0.66346 (11) | 0.0192 (4) | |
H11B | 0.853477 | 0.453906 | 0.696747 | 0.023* | |
C11C | 1.09807 (16) | 0.04553 (15) | −0.66239 (11) | 0.0187 (4) | |
H11C | 1.174597 | 0.022944 | −0.694008 | 0.022* | |
C12 | 0.63237 (16) | 0.38987 (15) | 0.57499 (11) | 0.0186 (4) | |
H12 | 0.708552 | 0.366292 | 0.542639 | 0.022* | |
C12A | 0.64776 (16) | 0.00269 (15) | −0.58628 (11) | 0.0179 (4) | |
H12A | 0.641058 | 0.071506 | −0.570813 | 0.021* | |
C12B | 0.86200 (16) | 0.48764 (15) | 0.58844 (11) | 0.0181 (4) | |
H12B | 0.872754 | 0.418489 | 0.570389 | 0.022* | |
C12C | 1.07081 (16) | 0.08399 (15) | −0.58800 (10) | 0.0175 (4) | |
H12C | 1.128572 | 0.087303 | −0.568568 | 0.021* | |
H1N | 0.395 (2) | 0.554 (2) | 0.7950 (14) | 0.031 (6)* | |
H2N | 0.516 (2) | 0.518 (2) | 0.7822 (15) | 0.033 (7)* | |
H3N | 0.673 (2) | −0.200 (2) | −0.7689 (15) | 0.039 (8)* | |
H4N | 0.666 (2) | −0.097 (2) | −0.7876 (15) | 0.036 (7)* | |
H5N | 0.852 (2) | 0.576 (2) | 0.7920 (15) | 0.037 (7)* | |
H6N | 0.831 (2) | 0.685 (2) | 0.7808 (15) | 0.035 (7)* | |
H7N | 0.991 (2) | −0.009 (2) | −0.7789 (16) | 0.043 (8)* | |
H8N | 1.111 (2) | −0.047 (2) | −0.7869 (14) | 0.031 (7)* | |
H1W | 0.155 (2) | 0.1254 (19) | 0.1873 (15) | 0.064 (10)* | |
H2W | 0.1166 (15) | 0.1971 (18) | 0.1402 (12) | 0.031 (7)* | |
H3W | 0.3304 (17) | 0.4996 (15) | 0.1291 (17) | 0.056 (9)* | |
H4W | 0.358 (2) | 0.3993 (17) | 0.1527 (17) | 0.063 (10)* | |
H5W | 0.581 (2) | 0.531 (3) | 0.1053 (7) | 0.082 (12)* | |
H6W | 0.6785 (12) | 0.4633 (18) | 0.0554 (15) | 0.049 (8)* | |
H7W | 0.8265 (9) | −0.0080 (19) | 0.1414 (16) | 0.047 (8)* | |
H8W | 0.9269 (19) | −0.0950 (8) | 0.1270 (16) | 0.045 (8)* | |
H11W | 1.187 (2) | 0.110 (2) | 0.0020 (12) | 0.050 (9)* | |
H12W | 1.275 (2) | 0.0765 (15) | −0.0625 (13) | 0.057 (9)* | |
H13W | 1.1940 (18) | 0.4350 (14) | 0.0606 (13) | 0.052 (9)* | |
H14W | 1.2900 (18) | 0.400 (2) | 0.0029 (13) | 0.049 (8)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
K1 | 0.01762 (19) | 0.0189 (2) | 0.01943 (19) | −0.00785 (16) | −0.00678 (15) | 0.00224 (15) |
K2 | 0.0220 (2) | 0.0183 (2) | 0.0234 (2) | −0.00772 (16) | −0.00867 (17) | 0.00016 (16) |
K3 | 0.0264 (2) | 0.0278 (2) | 0.0359 (3) | −0.0133 (2) | −0.0032 (2) | −0.00333 (19) |
K4 | 0.0225 (2) | 0.0200 (2) | 0.0208 (2) | −0.00755 (17) | −0.00514 (17) | 0.00190 (16) |
S1 | 0.0161 (2) | 0.0179 (2) | 0.0145 (2) | −0.00651 (17) | −0.00479 (17) | −0.00092 (16) |
S1A | 0.0172 (2) | 0.0162 (2) | 0.0146 (2) | −0.00747 (17) | −0.00571 (17) | 0.00230 (16) |
S1B | 0.0171 (2) | 0.0197 (2) | 0.0143 (2) | −0.00834 (18) | −0.00570 (17) | 0.00287 (17) |
S1C | 0.0157 (2) | 0.0162 (2) | 0.0139 (2) | −0.00658 (17) | −0.00328 (17) | −0.00098 (16) |
O1 | 0.0270 (7) | 0.0178 (7) | 0.0206 (7) | −0.0065 (6) | −0.0051 (6) | −0.0022 (5) |
O1A | 0.0317 (8) | 0.0200 (7) | 0.0152 (6) | −0.0124 (6) | −0.0034 (6) | 0.0026 (5) |
O1B | 0.0400 (9) | 0.0211 (7) | 0.0234 (7) | −0.0050 (6) | −0.0159 (7) | −0.0036 (6) |
O2 | 0.0198 (7) | 0.0300 (8) | 0.0218 (7) | −0.0090 (6) | −0.0092 (6) | −0.0023 (6) |
O1W | 0.0237 (7) | 0.0269 (8) | 0.0246 (7) | −0.0088 (6) | −0.0068 (6) | 0.0037 (6) |
O2A | 0.0293 (8) | 0.0171 (7) | 0.0213 (7) | −0.0045 (6) | −0.0112 (6) | −0.0021 (5) |
O2B | 0.0412 (9) | 0.0249 (7) | 0.0153 (7) | −0.0181 (7) | −0.0031 (6) | 0.0030 (6) |
O3 | 0.0229 (7) | 0.0296 (8) | 0.0167 (7) | −0.0136 (6) | −0.0045 (6) | 0.0044 (6) |
O2W | 0.0238 (8) | 0.0273 (8) | 0.0330 (8) | −0.0092 (7) | −0.0102 (7) | 0.0027 (7) |
O3A | 0.0242 (7) | 0.0443 (9) | 0.0244 (7) | −0.0199 (7) | −0.0127 (6) | 0.0090 (7) |
O3B | 0.0242 (8) | 0.0722 (12) | 0.0224 (8) | −0.0264 (8) | −0.0114 (6) | 0.0106 (8) |
O3W | 0.0290 (8) | 0.0219 (7) | 0.0251 (8) | −0.0075 (6) | −0.0105 (6) | 0.0018 (6) |
O4W | 0.0220 (8) | 0.0272 (8) | 0.0359 (9) | −0.0093 (6) | −0.0101 (7) | 0.0025 (7) |
O5W | 0.0285 (8) | 0.0292 (8) | 0.0333 (8) | −0.0107 (7) | −0.0159 (7) | 0.0064 (7) |
O6W | 0.0253 (8) | 0.0214 (7) | 0.0206 (7) | −0.0071 (6) | −0.0060 (6) | −0.0036 (6) |
O7W | 0.0297 (8) | 0.0208 (7) | 0.0230 (7) | −0.0084 (6) | −0.0059 (6) | 0.0009 (6) |
O8W | 0.0272 (8) | 0.0265 (8) | 0.0303 (8) | −0.0103 (6) | −0.0122 (7) | 0.0040 (6) |
O1C | 0.0169 (9) | 0.0284 (12) | 0.0186 (7) | −0.0099 (9) | −0.0004 (6) | −0.0047 (8) |
O2C | 0.0276 (12) | 0.0219 (8) | 0.0209 (8) | −0.0156 (8) | −0.0011 (8) | −0.0036 (6) |
O3C | 0.0296 (10) | 0.0208 (10) | 0.0174 (9) | −0.0041 (7) | −0.0102 (8) | 0.0018 (7) |
O4C | 0.0169 (9) | 0.0284 (12) | 0.0186 (7) | −0.0099 (9) | −0.0004 (6) | −0.0047 (8) |
O5C | 0.0276 (12) | 0.0219 (8) | 0.0209 (8) | −0.0156 (8) | −0.0011 (8) | −0.0036 (6) |
O6C | 0.0296 (10) | 0.0208 (10) | 0.0174 (9) | −0.0041 (7) | −0.0102 (8) | 0.0018 (7) |
N1 | 0.0179 (8) | 0.0182 (8) | 0.0163 (7) | −0.0079 (6) | −0.0054 (6) | 0.0003 (6) |
N1A | 0.0177 (8) | 0.0191 (8) | 0.0155 (7) | −0.0076 (6) | −0.0052 (6) | 0.0009 (6) |
N1B | 0.0176 (8) | 0.0194 (8) | 0.0169 (8) | −0.0079 (6) | −0.0059 (6) | 0.0013 (6) |
N1C | 0.0181 (8) | 0.0173 (7) | 0.0156 (7) | −0.0076 (6) | −0.0049 (6) | 0.0001 (6) |
N2 | 0.0182 (8) | 0.0168 (8) | 0.0168 (7) | −0.0074 (6) | −0.0052 (6) | 0.0003 (6) |
N2A | 0.0163 (8) | 0.0198 (8) | 0.0160 (8) | −0.0066 (6) | −0.0046 (6) | 0.0010 (6) |
N2B | 0.0152 (7) | 0.0193 (8) | 0.0163 (8) | −0.0060 (6) | −0.0043 (6) | 0.0008 (6) |
N2C | 0.0182 (8) | 0.0175 (8) | 0.0163 (7) | −0.0067 (6) | −0.0054 (6) | 0.0005 (6) |
N3 | 0.0243 (9) | 0.0227 (9) | 0.0179 (8) | −0.0096 (8) | −0.0079 (7) | 0.0004 (7) |
N3A | 0.0252 (9) | 0.0265 (9) | 0.0183 (8) | −0.0116 (8) | −0.0081 (7) | 0.0016 (7) |
N3B | 0.0217 (9) | 0.0293 (10) | 0.0182 (8) | −0.0073 (8) | −0.0069 (7) | −0.0027 (7) |
N3C | 0.0244 (9) | 0.0233 (9) | 0.0165 (8) | −0.0070 (8) | −0.0064 (7) | −0.0016 (7) |
C1 | 0.0159 (8) | 0.0132 (8) | 0.0147 (8) | −0.0058 (7) | −0.0045 (7) | 0.0018 (7) |
C1A | 0.0121 (8) | 0.0167 (8) | 0.0137 (8) | −0.0052 (7) | −0.0030 (7) | 0.0009 (7) |
C1B | 0.0128 (8) | 0.0182 (9) | 0.0138 (8) | −0.0059 (7) | −0.0035 (7) | 0.0010 (7) |
C1C | 0.0173 (9) | 0.0136 (8) | 0.0138 (8) | −0.0064 (7) | −0.0044 (7) | 0.0006 (6) |
C2 | 0.0152 (9) | 0.0183 (9) | 0.0195 (9) | −0.0070 (7) | −0.0061 (7) | 0.0013 (7) |
C2A | 0.0177 (9) | 0.0176 (9) | 0.0181 (9) | −0.0084 (7) | −0.0058 (7) | 0.0039 (7) |
C2B | 0.0180 (9) | 0.0178 (9) | 0.0172 (9) | −0.0081 (7) | −0.0055 (7) | 0.0045 (7) |
C2C | 0.0146 (8) | 0.0173 (9) | 0.0172 (9) | −0.0065 (7) | −0.0034 (7) | 0.0011 (7) |
C3 | 0.0142 (9) | 0.0198 (9) | 0.0199 (9) | −0.0067 (7) | −0.0034 (7) | 0.0000 (7) |
C3A | 0.0177 (9) | 0.0157 (9) | 0.0182 (9) | −0.0077 (7) | −0.0051 (7) | 0.0009 (7) |
C3B | 0.0168 (9) | 0.0157 (9) | 0.0190 (9) | −0.0078 (7) | −0.0046 (7) | 0.0018 (7) |
C3C | 0.0173 (9) | 0.0166 (9) | 0.0174 (9) | −0.0080 (7) | −0.0057 (7) | 0.0012 (7) |
C4 | 0.0187 (9) | 0.0127 (8) | 0.0158 (8) | −0.0064 (7) | −0.0053 (7) | 0.0011 (7) |
C4A | 0.0130 (8) | 0.0186 (9) | 0.0161 (9) | −0.0064 (7) | −0.0048 (7) | 0.0021 (7) |
C4B | 0.0128 (8) | 0.0202 (9) | 0.0147 (8) | −0.0057 (7) | −0.0044 (7) | 0.0020 (7) |
C4C | 0.0171 (9) | 0.0126 (8) | 0.0153 (8) | −0.0057 (7) | −0.0036 (7) | 0.0010 (7) |
C5 | 0.0151 (8) | 0.0179 (9) | 0.0191 (9) | −0.0075 (7) | −0.0066 (7) | 0.0009 (7) |
C5A | 0.0193 (9) | 0.0178 (9) | 0.0178 (9) | −0.0083 (7) | −0.0064 (7) | 0.0051 (7) |
C5B | 0.0203 (9) | 0.0172 (9) | 0.0172 (9) | −0.0084 (7) | −0.0059 (7) | 0.0045 (7) |
C5C | 0.0150 (9) | 0.0200 (9) | 0.0174 (9) | −0.0067 (7) | −0.0030 (7) | −0.0004 (7) |
C6 | 0.0153 (9) | 0.0193 (9) | 0.0187 (9) | −0.0069 (7) | −0.0039 (7) | −0.0007 (7) |
C6A | 0.0187 (9) | 0.0151 (8) | 0.0173 (9) | −0.0077 (7) | −0.0058 (7) | 0.0019 (7) |
C6B | 0.0183 (9) | 0.0165 (9) | 0.0181 (9) | −0.0079 (7) | −0.0043 (7) | 0.0009 (7) |
C6C | 0.0156 (9) | 0.0198 (9) | 0.0182 (9) | −0.0078 (7) | −0.0066 (7) | 0.0012 (7) |
C7 | 0.0181 (9) | 0.0137 (8) | 0.0161 (8) | −0.0072 (7) | −0.0054 (7) | 0.0018 (7) |
C7A | 0.0145 (8) | 0.0179 (9) | 0.0152 (8) | −0.0068 (7) | −0.0045 (7) | 0.0006 (7) |
C7B | 0.0131 (8) | 0.0193 (9) | 0.0150 (8) | −0.0061 (7) | −0.0029 (7) | 0.0005 (7) |
C7C | 0.0185 (9) | 0.0138 (8) | 0.0137 (8) | −0.0059 (7) | −0.0052 (7) | 0.0020 (7) |
C8 | 0.0168 (9) | 0.0184 (9) | 0.0179 (9) | −0.0082 (7) | −0.0055 (7) | 0.0027 (7) |
C8A | 0.0156 (9) | 0.0189 (9) | 0.0197 (9) | −0.0071 (7) | −0.0065 (7) | 0.0038 (7) |
C8B | 0.0168 (9) | 0.0182 (9) | 0.0205 (9) | −0.0073 (7) | −0.0067 (7) | 0.0023 (7) |
C8C | 0.0169 (9) | 0.0175 (9) | 0.0184 (9) | −0.0069 (7) | −0.0050 (7) | 0.0021 (7) |
C9 | 0.0169 (9) | 0.0202 (9) | 0.0176 (9) | −0.0075 (7) | −0.0033 (7) | 0.0021 (7) |
C9A | 0.0166 (9) | 0.0170 (9) | 0.0205 (9) | −0.0067 (7) | −0.0055 (7) | −0.0003 (7) |
C9B | 0.0163 (9) | 0.0189 (9) | 0.0218 (9) | −0.0067 (7) | −0.0060 (7) | −0.0029 (7) |
C9C | 0.0190 (9) | 0.0185 (9) | 0.0207 (9) | −0.0081 (7) | −0.0095 (8) | 0.0029 (7) |
C10 | 0.0229 (9) | 0.0134 (8) | 0.0157 (8) | −0.0081 (7) | −0.0073 (7) | 0.0039 (7) |
C10A | 0.0118 (8) | 0.0216 (9) | 0.0179 (9) | −0.0054 (7) | −0.0045 (7) | −0.0009 (7) |
C10B | 0.0113 (8) | 0.0235 (9) | 0.0171 (9) | −0.0057 (7) | −0.0041 (7) | −0.0012 (7) |
C10C | 0.0223 (9) | 0.0123 (8) | 0.0150 (8) | −0.0057 (7) | −0.0067 (7) | 0.0023 (7) |
C11 | 0.0175 (9) | 0.0176 (9) | 0.0226 (9) | −0.0079 (7) | −0.0101 (8) | 0.0019 (7) |
C11A | 0.0213 (9) | 0.0214 (9) | 0.0192 (9) | −0.0109 (8) | −0.0073 (8) | 0.0060 (7) |
C11B | 0.0196 (9) | 0.0219 (9) | 0.0182 (9) | −0.0096 (8) | −0.0072 (7) | 0.0051 (7) |
C11C | 0.0182 (9) | 0.0197 (9) | 0.0181 (9) | −0.0083 (7) | −0.0042 (7) | 0.0023 (7) |
C12 | 0.0169 (9) | 0.0172 (9) | 0.0213 (9) | −0.0069 (7) | −0.0048 (7) | 0.0010 (7) |
C12A | 0.0191 (9) | 0.0174 (9) | 0.0195 (9) | −0.0089 (7) | −0.0072 (7) | 0.0023 (7) |
C12B | 0.0175 (9) | 0.0186 (9) | 0.0190 (9) | −0.0081 (7) | −0.0053 (7) | 0.0005 (7) |
C12C | 0.0156 (9) | 0.0196 (9) | 0.0185 (9) | −0.0073 (7) | −0.0066 (7) | 0.0018 (7) |
K1—O2 | 2.6531 (14) | N2C—C7C | 1.421 (2) |
K1—O1Ai | 2.6570 (14) | N3—C10 | 1.402 (2) |
K1—O6Wii | 2.7388 (15) | N3—H1N | 0.92 (3) |
K1—O7Wii | 2.7669 (15) | N3—H2N | 0.81 (3) |
K1—O1W | 2.7806 (15) | N3A—C10A | 1.382 (2) |
K1—O1A | 2.8284 (14) | N3A—H3N | 0.82 (3) |
K1—O2A | 2.9928 (15) | N3A—H4N | 0.88 (3) |
K1—S1A | 3.4580 (6) | N3B—C10B | 1.392 (2) |
K1—K4ii | 4.1781 (6) | N3B—H5N | 0.90 (3) |
K1—K2 | 4.2073 (6) | N3B—H6N | 0.88 (3) |
K1—K1i | 4.4315 (8) | N3C—C10C | 1.405 (2) |
K2—O3 | 2.7462 (14) | N3C—H7N | 0.86 (3) |
K2—O1C | 2.7536 (17) | N3C—H8N | 0.87 (3) |
K2—O4C | 2.784 (14) | C1—C2 | 1.385 (2) |
K2—O2A | 2.7929 (14) | C1—C6 | 1.399 (3) |
K2—O2W | 2.8559 (16) | C1A—C2A | 1.393 (3) |
K2—O3Wiii | 2.8666 (15) | C1A—C6A | 1.395 (2) |
K2—O3W | 2.8901 (16) | C1B—C6B | 1.393 (3) |
K2—O2 | 3.0708 (15) | C1B—C2B | 1.395 (3) |
K2—O3A | 3.1446 (16) | C1C—C2C | 1.392 (3) |
K2—S1 | 3.4381 (6) | C1C—C6C | 1.396 (3) |
K2—S1A | 3.4869 (6) | C2—C3 | 1.391 (3) |
K2—K2iii | 3.9929 (8) | C2—H2 | 0.9500 |
K2—H6W | 3.00 (3) | C2A—C3A | 1.390 (3) |
K3—O3 | 2.6206 (14) | C2A—H2A | 0.9500 |
K3—O3C | 2.649 (2) | C2B—C3B | 1.386 (3) |
K3—O1B | 2.7285 (16) | C2B—H2B | 0.9500 |
K3—O5Wiv | 2.8713 (16) | C2C—C3C | 1.391 (2) |
K3—O4W | 2.8932 (16) | C2C—H2C | 0.9500 |
K3—O5W | 2.9166 (15) | C3—C4 | 1.394 (3) |
K3—O6C | 3.181 (17) | C3—H3 | 0.9500 |
K3—O3B | 3.2009 (19) | C3A—C4A | 1.396 (3) |
K3—O4C | 3.261 (16) | C3A—H3A | 0.9500 |
K3—O4Wiv | 3.2971 (17) | C3B—C4B | 1.393 (3) |
K3—S1B | 3.5219 (7) | C3B—H3B | 0.9500 |
K3—K3iv | 3.6855 (9) | C3C—C4C | 1.393 (3) |
K3—H9Wiv | 2.48 (2) | C3C—H3C | 0.9500 |
K4—O6C | 2.542 (17) | C4—C5 | 1.395 (3) |
K4—O2Bv | 2.6854 (15) | C4A—C5A | 1.394 (3) |
K4—O6W | 2.7164 (15) | C4B—C5B | 1.393 (3) |
K4—O2B | 2.7701 (15) | C4C—C5C | 1.393 (3) |
K4—O8W | 2.8338 (16) | C5—C6 | 1.384 (3) |
K4—O7W | 2.8395 (16) | C5—H5 | 0.9500 |
K4—O3C | 2.954 (2) | C5A—C6A | 1.388 (3) |
K4—O2C | 3.097 (2) | C5A—H5A | 0.9500 |
K4—O1B | 3.1503 (16) | C5B—C6B | 1.389 (3) |
K4—S1B | 3.4918 (6) | C5B—H5B | 0.9500 |
K4—S1C | 3.6089 (6) | C5C—C6C | 1.387 (2) |
S1—O2 | 1.4497 (14) | C5C—H5C | 0.9500 |
S1—O3 | 1.4565 (14) | C6—H6 | 0.9500 |
S1—O1 | 1.4664 (14) | C6A—H6A | 0.9500 |
S1—C1 | 1.7680 (18) | C6B—H6B | 0.9500 |
S1A—O1A | 1.4452 (14) | C6C—H6C | 0.9500 |
S1A—O3A | 1.4564 (14) | C7—C12 | 1.395 (3) |
S1A—O2A | 1.4691 (14) | C7—C8 | 1.401 (3) |
S1A—C1A | 1.7690 (18) | C7A—C8A | 1.396 (3) |
S1B—O2B | 1.4447 (14) | C7A—C12A | 1.404 (3) |
S1B—O3B | 1.4519 (15) | C7B—C8B | 1.395 (3) |
S1B—O1B | 1.4635 (15) | C7B—C12B | 1.399 (3) |
S1B—C1B | 1.7706 (18) | C7C—C8C | 1.393 (3) |
S1C—O6C | 1.380 (16) | C7C—C12C | 1.400 (3) |
S1C—O4C | 1.421 (15) | C8—C9 | 1.380 (3) |
S1C—O5C | 1.453 (13) | C8—H8 | 0.9500 |
S1C—O1C | 1.4562 (18) | C8A—C9A | 1.386 (3) |
S1C—O2C | 1.4592 (17) | C8A—H8A | 0.9500 |
S1C—O3C | 1.4715 (18) | C8B—C9B | 1.390 (3) |
S1C—C1C | 1.7670 (18) | C8B—H8B | 0.9500 |
O1W—H1W | 0.871 (10) | C8C—C9C | 1.390 (3) |
O1W—H2W | 0.869 (9) | C8C—H8C | 0.9500 |
O2W—H3W | 0.866 (10) | C9—C10 | 1.401 (3) |
O2W—H4W | 0.869 (10) | C9—H9 | 0.9500 |
O3W—H5W | 0.867 (10) | C9A—C10A | 1.402 (3) |
O3W—H6W | 0.869 (10) | C9A—H9A | 0.9500 |
O4W—H7W | 0.873 (10) | C9B—C10B | 1.400 (3) |
O4W—H8W | 0.867 (10) | C9B—H9B | 0.9500 |
O5W—H9W | 0.870 (9) | C9C—C10C | 1.391 (3) |
O5W—H10W | 0.888 (9) | C9C—H9C | 0.9500 |
O6W—H11W | 0.866 (10) | C10—C11 | 1.392 (3) |
O6W—H12W | 0.862 (10) | C10A—C11A | 1.409 (3) |
O7W—H13W | 0.873 (10) | C10B—C11B | 1.404 (3) |
O7W—H14W | 0.876 (10) | C10C—C11C | 1.401 (3) |
O8W—H15W | 0.882 (9) | C11—C12 | 1.391 (3) |
O8W—H16W | 0.870 (9) | C11—H11 | 0.9500 |
N1—N2 | 1.260 (2) | C11A—C12A | 1.378 (3) |
N1—C4 | 1.425 (2) | C11A—H11A | 0.9500 |
N1A—N2A | 1.265 (2) | C11B—C12B | 1.377 (3) |
N1A—C4A | 1.430 (2) | C11B—H11B | 0.9500 |
N1B—N2B | 1.263 (2) | C11C—C12C | 1.381 (3) |
N1B—C4B | 1.429 (2) | C11C—H11C | 0.9500 |
N1C—N2C | 1.259 (2) | C12—H12 | 0.9500 |
N1C—C4C | 1.429 (2) | C12A—H12A | 0.9500 |
N2—C7 | 1.421 (2) | C12B—H12B | 0.9500 |
N2A—C7A | 1.415 (2) | C12C—H12C | 0.9500 |
N2B—C7B | 1.420 (2) | ||
O2—K1—O1Ai | 93.46 (5) | O1A—S1A—K2 | 112.62 (6) |
O2—K1—O6Wii | 176.42 (5) | O3A—S1A—K2 | 64.38 (6) |
O1Ai—K1—O6Wii | 88.31 (4) | O2A—S1A—K2 | 50.50 (6) |
O2—K1—O7Wii | 96.46 (5) | C1A—S1A—K2 | 139.34 (6) |
O1Ai—K1—O7Wii | 166.72 (5) | K1—S1A—K2 | 74.573 (13) |
O6Wii—K1—O7Wii | 82.29 (4) | O2B—S1B—O3B | 114.07 (10) |
O2—K1—O1W | 106.10 (5) | O2B—S1B—O1B | 111.81 (9) |
O1Ai—K1—O1W | 81.52 (4) | O3B—S1B—O1B | 110.35 (10) |
O6Wii—K1—O1W | 77.24 (5) | O2B—S1B—C1B | 107.17 (9) |
O7Wii—K1—O1W | 87.25 (5) | O3B—S1B—C1B | 106.78 (9) |
O2—K1—O1A | 86.00 (4) | O1B—S1B—C1B | 106.18 (8) |
O1Ai—K1—O1A | 72.27 (5) | O2B—S1B—K4 | 49.10 (6) |
O6Wii—K1—O1A | 91.58 (4) | O3B—S1B—K4 | 120.29 (6) |
O7Wii—K1—O1A | 117.16 (4) | O1B—S1B—K4 | 64.44 (6) |
O1W—K1—O1A | 151.82 (4) | C1B—S1B—K4 | 132.51 (6) |
O2—K1—O2A | 84.65 (4) | O2B—S1B—K3 | 121.36 (6) |
O1Ai—K1—O2A | 121.15 (4) | O3B—S1B—K3 | 65.35 (8) |
O6Wii—K1—O2A | 91.77 (4) | O1B—S1B—K3 | 46.46 (6) |
O7Wii—K1—O2A | 68.76 (4) | C1B—S1B—K3 | 129.95 (6) |
O1W—K1—O2A | 154.89 (4) | K4—S1B—K3 | 79.306 (14) |
O1A—K1—O2A | 48.89 (4) | O6C—S1C—O4C | 113.4 (8) |
O2—K1—S1A | 83.01 (3) | O6C—S1C—O5C | 117.1 (8) |
O1Ai—K1—S1A | 96.24 (3) | O4C—S1C—O5C | 112.0 (8) |
O6Wii—K1—S1A | 93.70 (3) | O1C—S1C—O2C | 112.83 (10) |
O7Wii—K1—S1A | 93.72 (3) | O1C—S1C—O3C | 112.65 (11) |
O1W—K1—S1A | 170.69 (4) | O2C—S1C—O3C | 110.62 (11) |
O1A—K1—S1A | 24.01 (3) | O6C—S1C—C1C | 105.1 (6) |
O2A—K1—S1A | 25.02 (3) | O4C—S1C—C1C | 105.8 (6) |
O2—K1—K4ii | 138.74 (3) | O5C—S1C—C1C | 101.8 (5) |
O1Ai—K1—K4ii | 127.69 (3) | O1C—S1C—C1C | 107.36 (9) |
O6Wii—K1—K4ii | 39.82 (3) | O2C—S1C—C1C | 106.53 (9) |
O7Wii—K1—K4ii | 42.49 (3) | O3C—S1C—C1C | 106.40 (9) |
O1W—K1—K4ii | 80.55 (3) | O6C—S1C—K4 | 31.8 (7) |
O1A—K1—K4ii | 107.32 (3) | O4C—S1C—K4 | 126.2 (6) |
O2A—K1—K4ii | 76.73 (3) | O5C—S1C—K4 | 85.8 (7) |
S1A—K1—K4ii | 93.909 (13) | O1C—S1C—K4 | 132.42 (7) |
O2—K1—K2 | 46.70 (3) | O2C—S1C—K4 | 58.12 (9) |
O1Ai—K1—K2 | 126.75 (3) | O3C—S1C—K4 | 52.50 (9) |
O6Wii—K1—K2 | 129.93 (3) | C1C—S1C—K4 | 120.10 (6) |
O7Wii—K1—K2 | 66.47 (3) | O6C—S1C—K3 | 54.9 (7) |
O1W—K1—K2 | 135.07 (3) | O4C—S1C—K3 | 58.5 (7) |
O1A—K1—K2 | 71.44 (3) | O5C—S1C—K3 | 139.2 (5) |
O2A—K1—K2 | 41.51 (3) | O1C—S1C—K3 | 80.14 (9) |
S1A—K1—K2 | 53.027 (11) | O2C—S1C—K3 | 126.37 (8) |
K4ii—K1—K2 | 99.729 (12) | O3C—S1C—K3 | 32.52 (9) |
O2—K1—K1i | 89.53 (3) | C1C—S1C—K3 | 119.03 (6) |
O1Ai—K1—K1i | 37.44 (3) | K4—S1C—K3 | 74.665 (13) |
O6Wii—K1—K1i | 89.99 (3) | S1A—O1A—K1i | 148.88 (8) |
O7Wii—K1—K1i | 151.03 (4) | S1A—O1A—K1 | 103.22 (7) |
O1W—K1—K1i | 118.31 (3) | K1i—O1A—K1 | 107.73 (5) |
O1A—K1—K1i | 34.83 (3) | S1B—O1B—K3 | 110.66 (8) |
O2A—K1—K1i | 83.71 (3) | S1B—O1B—K4 | 90.78 (7) |
S1A—K1—K1i | 58.808 (12) | K3—O1B—K4 | 98.91 (4) |
K4ii—K1—K1i | 123.824 (16) | S1—O2—K1 | 152.11 (8) |
K2—K1—K1i | 98.949 (14) | S1—O2—K2 | 91.86 (7) |
O3—K2—O1C | 89.81 (6) | K1—O2—K2 | 94.34 (4) |
O3—K2—O4C | 78.8 (3) | K1—O1W—H1W | 132 (2) |
O3—K2—O2A | 109.42 (4) | K1—O1W—H2W | 104.3 (16) |
O1C—K2—O2A | 110.70 (5) | H1W—O1W—H2W | 99.6 (18) |
O4C—K2—O2A | 108.2 (3) | S1A—O2A—K2 | 105.55 (7) |
O3—K2—O2W | 90.13 (4) | S1A—O2A—K1 | 95.50 (7) |
O1C—K2—O2W | 136.34 (5) | K2—O2A—K1 | 93.24 (4) |
O4C—K2—O2W | 141.4 (3) | S1B—O2B—K4v | 148.49 (9) |
O2A—K2—O2W | 110.39 (5) | S1B—O2B—K4 | 107.69 (7) |
O3—K2—O3Wiii | 166.01 (5) | K4v—O2B—K4 | 103.59 (5) |
O1C—K2—O3Wiii | 103.96 (6) | S1—O3—K3 | 139.98 (8) |
O2A—K2—O3Wiii | 68.31 (4) | S1—O3—K2 | 105.64 (7) |
O2W—K2—O3Wiii | 78.26 (4) | K3—O3—K2 | 113.39 (5) |
O3—K2—O3W | 91.51 (4) | K2—O2W—H3W | 113 (2) |
O1C—K2—O3W | 64.79 (5) | K2—O2W—H4W | 105 (2) |
O4C—K2—O3W | 71.9 (3) | H3W—O2W—H4W | 102.9 (19) |
O2A—K2—O3W | 158.82 (4) | S1A—O3A—K2 | 90.93 (7) |
O2W—K2—O3W | 71.57 (5) | S1B—O3B—K3 | 90.31 (8) |
O3Wiii—K2—O3W | 92.17 (4) | K2iii—O3W—K2 | 87.83 (4) |
O3—K2—O2 | 48.75 (4) | K2iii—O3W—H5W | 101 (2) |
O1C—K2—O2 | 137.53 (6) | K2—O3W—H5W | 118 (2) |
O4C—K2—O2 | 125.3 (3) | K2iii—O3W—H6W | 156.1 (18) |
O2A—K2—O2 | 80.89 (4) | K2—O3W—H6W | 89.1 (19) |
O2W—K2—O2 | 63.80 (4) | H5W—O3W—H6W | 101.7 (19) |
O3Wiii—K2—O2 | 117.99 (4) | K3—O4W—K3iv | 72.75 (4) |
O3W—K2—O2 | 116.97 (4) | K3—O4W—H7W | 98.2 (17) |
O3—K2—O3A | 79.15 (4) | K3iv—O4W—H7W | 125.5 (19) |
O1C—K2—O3A | 75.40 (5) | K3—O4W—H8W | 138.6 (18) |
O4C—K2—O3A | 67.3 (3) | K3iv—O4W—H8W | 66.2 (18) |
O2A—K2—O3A | 47.21 (4) | H7W—O4W—H8W | 101.3 (18) |
O2W—K2—O3A | 146.90 (4) | K3iv—O5W—K3 | 79.10 (4) |
O3Wiii—K2—O3A | 106.42 (4) | K3iv—O5W—H9W | 54.9 (17) |
O3W—K2—O3A | 139.15 (4) | K3—O5W—H9W | 94.2 (15) |
O2—K2—O3A | 86.27 (4) | K3iv—O5W—H10W | 105.4 (16) |
O3—K2—S1 | 24.08 (3) | K3—O5W—H10W | 173.6 (15) |
O1C—K2—S1 | 113.82 (5) | H9W—O5W—H10W | 92.1 (15) |
O4C—K2—S1 | 102.4 (3) | K4—O6W—K1vi | 99.97 (5) |
O2A—K2—S1 | 97.78 (3) | K4—O6W—H11W | 110.5 (18) |
O2W—K2—S1 | 74.17 (3) | K1vi—O6W—H11W | 102 (2) |
O3Wiii—K2—S1 | 142.21 (4) | K4—O6W—H12W | 132.8 (19) |
O3W—K2—S1 | 102.89 (3) | K1vi—O6W—H12W | 104 (2) |
O2—K2—S1 | 24.93 (3) | H11W—O6W—H12W | 103.3 (18) |
O3A—K2—S1 | 84.46 (3) | K1vi—O7W—K4 | 96.35 (5) |
O3—K2—S1A | 90.20 (3) | K1vi—O7W—H13W | 138.7 (18) |
O1C—K2—S1A | 97.37 (4) | K4—O7W—H13W | 103.0 (19) |
O4C—K2—S1A | 90.9 (3) | K1vi—O7W—H14W | 108.2 (17) |
O2A—K2—S1A | 23.95 (3) | K4—O7W—H14W | 109.1 (19) |
O2W—K2—S1A | 126.29 (4) | H13W—O7W—H14W | 99.4 (17) |
O3Wiii—K2—S1A | 90.46 (3) | K4—O8W—H15W | 114.6 (16) |
O3W—K2—S1A | 162.07 (4) | K4—O8W—H16W | 124.1 (16) |
O2—K2—S1A | 76.98 (3) | H15W—O8W—H16W | 98.9 (16) |
O3A—K2—S1A | 24.68 (3) | S1C—O1C—K2 | 160.77 (14) |
S1—K2—S1A | 85.573 (14) | S1C—O2C—K4 | 98.29 (10) |
O3—K2—K2iii | 135.69 (3) | S1C—O3C—K3 | 130.10 (12) |
O1C—K2—K2iii | 82.24 (5) | S1C—O3C—K4 | 104.22 (11) |
O2A—K2—K2iii | 114.18 (3) | K3—O3C—K4 | 105.93 (6) |
O2W—K2—K2iii | 67.98 (3) | S1C—O4C—K2 | 161.7 (10) |
O3Wiii—K2—K2iii | 46.33 (3) | S1C—O4C—K3 | 99.6 (7) |
O3W—K2—K2iii | 45.84 (3) | K2—O4C—K3 | 95.5 (4) |
O2—K2—K2iii | 131.69 (3) | S1C—O6C—K4 | 131.6 (9) |
O3A—K2—K2iii | 138.62 (3) | S1C—O6C—K3 | 104.4 (9) |
S1—K2—K2iii | 136.779 (19) | K4—O6C—K3 | 102.3 (5) |
S1A—K2—K2iii | 133.976 (19) | N2—N1—C4 | 113.70 (15) |
O3—K2—H6W | 78.2 (4) | N2A—N1A—C4A | 113.11 (15) |
O1C—K2—H6W | 55.3 (4) | N2B—N1B—C4B | 113.55 (15) |
O4C—K2—H6W | 59.6 (5) | N2C—N1C—C4C | 113.74 (15) |
O2A—K2—H6W | 164.9 (5) | N1—N2—C7 | 113.51 (15) |
O2W—K2—H6W | 82.1 (4) | N1A—N2A—C7A | 114.38 (15) |
O3Wiii—K2—H6W | 107.5 (3) | N1B—N2B—C7B | 113.58 (15) |
O3W—K2—H6W | 16.8 (2) | N1C—N2C—C7C | 113.67 (15) |
O2—K2—H6W | 113.1 (5) | C10—N3—H1N | 117.5 (15) |
O3A—K2—H6W | 125.1 (3) | C10—N3—H2N | 113.3 (19) |
S1—K2—H6W | 93.8 (5) | H1N—N3—H2N | 111 (2) |
S1A—K2—H6W | 149.7 (3) | C10A—N3A—H3N | 114.1 (19) |
K2iii—K2—H6W | 61.5 (3) | C10A—N3A—H4N | 115.9 (17) |
O3—K3—O3C | 111.17 (5) | H3N—N3A—H4N | 112 (3) |
O3—K3—O1B | 116.49 (5) | C10B—N3B—H5N | 115.7 (17) |
O3C—K3—O1B | 81.50 (6) | C10B—N3B—H6N | 115.6 (17) |
O3—K3—O5Wiv | 75.72 (5) | H5N—N3B—H6N | 106 (2) |
O3C—K3—O5Wiv | 90.88 (6) | C10C—N3C—H7N | 112.5 (19) |
O1B—K3—O5Wiv | 167.29 (5) | C10C—N3C—H8N | 115.8 (16) |
O3—K3—O4W | 77.80 (4) | H7N—N3C—H8N | 113 (2) |
O3C—K3—O4W | 162.84 (5) | C2—C1—C6 | 121.15 (17) |
O1B—K3—O4W | 108.15 (5) | C2—C1—S1 | 119.32 (14) |
O5Wiv—K3—O4W | 76.90 (5) | C6—C1—S1 | 119.41 (14) |
O3—K3—O5W | 141.48 (5) | C2A—C1A—C6A | 120.45 (16) |
O3C—K3—O5W | 107.21 (5) | C2A—C1A—S1A | 120.64 (14) |
O1B—K3—O5W | 72.00 (4) | C6A—C1A—S1A | 118.89 (14) |
O5Wiv—K3—O5W | 100.90 (4) | C6B—C1B—C2B | 120.54 (17) |
O4W—K3—O5W | 64.31 (4) | C6B—C1B—S1B | 118.77 (14) |
O3—K3—O6C | 114.4 (3) | C2B—C1B—S1B | 120.67 (14) |
O1B—K3—O6C | 75.9 (3) | C2C—C1C—C6C | 120.71 (17) |
O5Wiv—K3—O6C | 96.3 (3) | C2C—C1C—S1C | 120.99 (14) |
O4W—K3—O6C | 164.5 (3) | C6C—C1C—S1C | 118.28 (14) |
O5W—K3—O6C | 104.1 (3) | C1—C2—C3 | 119.08 (17) |
O3—K3—O3B | 72.30 (4) | C1—C2—H2 | 120.5 |
O3C—K3—O3B | 83.22 (5) | C3—C2—H2 | 120.5 |
O1B—K3—O3B | 46.78 (4) | C3A—C2A—C1A | 119.91 (17) |
O5Wiv—K3—O3B | 142.66 (4) | C3A—C2A—H2A | 120.0 |
O4W—K3—O3B | 113.80 (5) | C1A—C2A—H2A | 120.0 |
O5W—K3—O3B | 116.10 (4) | C3B—C2B—C1B | 120.03 (17) |
O6C—K3—O3B | 80.1 (3) | C3B—C2B—H2B | 120.0 |
O3—K3—O4C | 72.3 (3) | C1B—C2B—H2B | 120.0 |
O1B—K3—O4C | 100.0 (3) | C3C—C2C—C1C | 119.71 (17) |
O5Wiv—K3—O4C | 79.8 (3) | C3C—C2C—H2C | 120.1 |
O4W—K3—O4C | 145.7 (3) | C1C—C2C—H2C | 120.1 |
O5W—K3—O4C | 145.8 (3) | C2—C3—C4 | 120.20 (17) |
O6C—K3—O4C | 42.6 (4) | C2—C3—H3 | 119.9 |
O3B—K3—O4C | 72.6 (3) | C4—C3—H3 | 119.9 |
O3—K3—O4Wiv | 131.51 (4) | C2A—C3A—C4A | 119.70 (17) |
O3C—K3—O4Wiv | 55.72 (5) | C2A—C3A—H3A | 120.1 |
O1B—K3—O4Wiv | 107.63 (4) | C4A—C3A—H3A | 120.1 |
O5Wiv—K3—O4Wiv | 59.69 (4) | C2B—C3B—C4B | 119.58 (17) |
O4W—K3—O4Wiv | 107.25 (4) | C2B—C3B—H3B | 120.2 |
O5W—K3—O4Wiv | 70.16 (4) | C4B—C3B—H3B | 120.2 |
O3B—K3—O4Wiv | 136.67 (4) | C2C—C3C—C4C | 119.64 (17) |
O3—K3—S1B | 96.20 (3) | C2C—C3C—H3C | 120.2 |
O3C—K3—S1B | 78.29 (4) | C4C—C3C—H3C | 120.2 |
O1B—K3—S1B | 22.88 (3) | C3—C4—C5 | 120.29 (17) |
O5Wiv—K3—S1B | 163.31 (4) | C3—C4—N1 | 114.87 (16) |
O4W—K3—S1B | 116.15 (4) | C5—C4—N1 | 124.83 (16) |
O5W—K3—S1B | 94.47 (3) | C5A—C4A—C3A | 120.20 (17) |
O6C—K3—S1B | 73.5 (3) | C5A—C4A—N1A | 115.36 (16) |
O3B—K3—S1B | 24.35 (3) | C3A—C4A—N1A | 124.43 (17) |
O4C—K3—S1B | 83.8 (3) | C5B—C4B—C3B | 120.33 (17) |
O4Wiv—K3—S1B | 121.09 (3) | C5B—C4B—N1B | 114.82 (16) |
O3—K3—K3iv | 115.28 (4) | C3B—C4B—N1B | 124.84 (17) |
O3C—K3—K3iv | 104.25 (4) | C5C—C4C—C3C | 120.44 (17) |
O1B—K3—K3iv | 121.03 (4) | C5C—C4C—N1C | 114.83 (16) |
O5Wiv—K3—K3iv | 50.99 (3) | C3C—C4C—N1C | 124.72 (16) |
O4W—K3—K3iv | 58.69 (3) | C6—C5—C4 | 119.71 (17) |
O5W—K3—K3iv | 49.91 (3) | C6—C5—H5 | 120.1 |
O3B—K3—K3iv | 165.36 (4) | C4—C5—H5 | 120.1 |
O4Wiv—K3—K3iv | 48.56 (3) | C6A—C5A—C4A | 120.13 (17) |
S1B—K3—K3iv | 143.90 (2) | C6A—C5A—H5A | 119.9 |
O3—K3—H9Wiv | 62.8 (4) | C4A—C5A—H5A | 119.9 |
O3C—K3—H9Wiv | 105.2 (4) | C6B—C5B—C4B | 120.25 (17) |
O1B—K3—H9Wiv | 173.2 (4) | C6B—C5B—H5B | 119.9 |
O5Wiv—K3—H9Wiv | 16.7 (3) | C4B—C5B—H5B | 119.9 |
O4W—K3—H9Wiv | 65.0 (4) | C6C—C5C—C4C | 120.11 (17) |
O5W—K3—H9Wiv | 104.2 (5) | C6C—C5C—H5C | 119.9 |
O3B—K3—H9Wiv | 134.4 (5) | C4C—C5C—H5C | 119.9 |
O4Wiv—K3—H9Wiv | 75.7 (3) | C5—C6—C1 | 119.55 (17) |
S1B—K3—H9Wiv | 158.7 (4) | C5—C6—H6 | 120.2 |
K3iv—K3—H9Wiv | 56.5 (5) | C1—C6—H6 | 120.2 |
O6C—K4—O6W | 87.6 (3) | C5A—C6A—C1A | 119.56 (17) |
O2Bv—K4—O6W | 158.58 (5) | C5A—C6A—H6A | 120.2 |
O6C—K4—O2B | 92.2 (4) | C1A—C6A—H6A | 120.2 |
O2Bv—K4—O2B | 76.41 (5) | C5B—C6B—C1B | 119.26 (17) |
O6W—K4—O2B | 111.99 (4) | C5B—C6B—H6B | 120.4 |
O6C—K4—O8W | 119.9 (4) | C1B—C6B—H6B | 120.4 |
O2Bv—K4—O8W | 75.67 (5) | C5C—C6C—C1C | 119.36 (17) |
O6W—K4—O8W | 87.78 (5) | C5C—C6C—H6C | 120.3 |
O2B—K4—O8W | 143.65 (5) | C1C—C6C—H6C | 120.3 |
O6C—K4—O7W | 163.8 (4) | C12—C7—C8 | 119.49 (17) |
O2Bv—K4—O7W | 80.59 (5) | C12—C7—N2 | 116.54 (16) |
O6W—K4—O7W | 81.35 (4) | C8—C7—N2 | 123.96 (16) |
O2B—K4—O7W | 81.20 (5) | C8A—C7A—C12A | 119.35 (17) |
O8W—K4—O7W | 71.68 (4) | C8A—C7A—N2A | 116.26 (16) |
O2Bv—K4—O3C | 119.29 (5) | C12A—C7A—N2A | 124.38 (16) |
O6W—K4—O3C | 81.43 (5) | C8B—C7B—C12B | 119.37 (17) |
O2B—K4—O3C | 88.02 (5) | C8B—C7B—N2B | 116.68 (16) |
O8W—K4—O3C | 126.13 (5) | C12B—C7B—N2B | 123.95 (17) |
O7W—K4—O3C | 154.52 (5) | C8C—C7C—C12C | 119.49 (17) |
O2Bv—K4—O2C | 72.75 (5) | C8C—C7C—N2C | 116.32 (16) |
O6W—K4—O2C | 126.89 (4) | C12C—C7C—N2C | 124.18 (16) |
O2B—K4—O2C | 81.89 (5) | C9—C8—C7 | 119.86 (17) |
O8W—K4—O2C | 111.10 (5) | C9—C8—H8 | 120.1 |
O7W—K4—O2C | 151.11 (4) | C7—C8—H8 | 120.1 |
O3C—K4—O2C | 46.87 (5) | C9A—C8A—C7A | 120.66 (17) |
O6C—K4—O1B | 79.0 (4) | C9A—C8A—H8A | 119.7 |
O2Bv—K4—O1B | 123.67 (4) | C7A—C8A—H8A | 119.7 |
O6W—K4—O1B | 66.06 (4) | C9B—C8B—C7B | 120.32 (17) |
O2B—K4—O1B | 47.47 (4) | C9B—C8B—H8B | 119.8 |
O8W—K4—O1B | 147.95 (4) | C7B—C8B—H8B | 119.8 |
O7W—K4—O1B | 85.73 (4) | C9C—C8C—C7C | 120.29 (17) |
O3C—K4—O1B | 70.13 (5) | C9C—C8C—H8C | 119.9 |
O2C—K4—O1B | 99.72 (4) | C7C—C8C—H8C | 119.9 |
O6C—K4—S1B | 81.9 (4) | C8—C9—C10 | 121.02 (17) |
O2Bv—K4—S1B | 99.57 (3) | C8—C9—H9 | 119.5 |
O6W—K4—S1B | 90.68 (3) | C10—C9—H9 | 119.5 |
O2B—K4—S1B | 23.22 (3) | C8A—C9A—C10A | 120.26 (17) |
O8W—K4—S1B | 158.02 (4) | C8A—C9A—H9A | 119.9 |
O7W—K4—S1B | 86.41 (3) | C10A—C9A—H9A | 119.9 |
O3C—K4—S1B | 75.16 (4) | C8B—C9B—C10B | 120.45 (17) |
O2C—K4—S1B | 87.21 (3) | C8B—C9B—H9B | 119.8 |
O1B—K4—S1B | 24.78 (3) | C10B—C9B—H9B | 119.8 |
O6C—K4—S1C | 16.6 (3) | C8C—C9C—C10C | 120.35 (17) |
O2Bv—K4—S1C | 96.17 (4) | C8C—C9C—H9C | 119.8 |
O6W—K4—S1C | 104.10 (3) | C10C—C9C—H9C | 119.8 |
O2B—K4—S1C | 84.45 (3) | C11—C10—C9 | 118.90 (17) |
O8W—K4—S1C | 121.29 (3) | C11—C10—N3 | 121.55 (17) |
O7W—K4—S1C | 165.64 (3) | C9—C10—N3 | 119.54 (18) |
O3C—K4—S1C | 23.28 (4) | N3A—C10A—C9A | 121.31 (18) |
O2C—K4—S1C | 23.58 (3) | N3A—C10A—C11A | 119.94 (18) |
O1B—K4—S1C | 84.49 (3) | C9A—C10A—C11A | 118.71 (17) |
S1B—K4—S1C | 80.317 (14) | N3B—C10B—C9B | 121.73 (18) |
O2Bv—K4—K1vi | 120.62 (4) | N3B—C10B—C11B | 119.62 (18) |
O6W—K4—K1vi | 40.21 (3) | C9B—C10B—C11B | 118.61 (17) |
O2B—K4—K1vi | 99.50 (3) | C9C—C10C—C11C | 119.19 (17) |
O8W—K4—K1vi | 75.67 (3) | C9C—C10C—N3C | 121.44 (18) |
O7W—K4—K1vi | 41.16 (3) | C11C—C10C—N3C | 119.35 (18) |
O3C—K4—K1vi | 119.71 (4) | C12—C11—C10 | 120.48 (17) |
O2C—K4—K1vi | 166.57 (3) | C12—C11—H11 | 119.8 |
O1B—K4—K1vi | 72.38 (3) | C10—C11—H11 | 119.8 |
S1B—K4—K1vi | 89.108 (13) | C12A—C11A—C10A | 120.94 (17) |
S1C—K4—K1vi | 142.993 (15) | C12A—C11A—H11A | 119.5 |
O2—S1—O3 | 112.68 (8) | C10A—C11A—H11A | 119.5 |
O2—S1—O1 | 113.18 (9) | C12B—C11B—C10B | 120.96 (17) |
O3—S1—O1 | 111.78 (8) | C12B—C11B—H11B | 119.5 |
O2—S1—C1 | 107.16 (8) | C10B—C11B—H11B | 119.5 |
O3—S1—C1 | 106.88 (8) | C12C—C11C—C10C | 120.65 (17) |
O1—S1—C1 | 104.50 (8) | C12C—C11C—H11C | 119.7 |
O2—S1—K2 | 63.22 (6) | C10C—C11C—H11C | 119.7 |
O3—S1—K2 | 50.28 (6) | C11—C12—C7 | 120.23 (17) |
O1—S1—K2 | 141.39 (6) | C11—C12—H12 | 119.9 |
C1—S1—K2 | 113.31 (6) | C7—C12—H12 | 119.9 |
O1A—S1A—O3A | 113.91 (9) | C11A—C12A—C7A | 120.02 (17) |
O1A—S1A—O2A | 111.82 (8) | C11A—C12A—H12A | 120.0 |
O3A—S1A—O2A | 110.19 (9) | C7A—C12A—H12A | 120.0 |
O1A—S1A—C1A | 107.12 (8) | C11B—C12B—C7B | 120.22 (17) |
O3A—S1A—C1A | 106.79 (8) | C11B—C12B—H12B | 119.9 |
O2A—S1A—C1A | 106.56 (8) | C7B—C12B—H12B | 119.9 |
O1A—S1A—K1 | 52.78 (6) | C11C—C12C—C7C | 120.01 (17) |
O3A—S1A—K1 | 126.06 (6) | C11C—C12C—H12C | 120.0 |
O2A—S1A—K1 | 59.48 (6) | C7C—C12C—H12C | 120.0 |
C1A—S1A—K1 | 127.14 (6) | ||
O3A—S1A—O1A—K1i | −55.79 (18) | O2B—S1B—C1B—C2B | 15.16 (17) |
O2A—S1A—O1A—K1i | 178.46 (14) | O3B—S1B—C1B—C2B | −107.45 (16) |
C1A—S1A—O1A—K1i | 62.06 (18) | O1B—S1B—C1B—C2B | 134.79 (15) |
K1—S1A—O1A—K1i | −173.9 (2) | K4—S1B—C1B—C2B | 64.89 (17) |
K2—S1A—O1A—K1i | −126.67 (14) | K3—S1B—C1B—C2B | −179.04 (11) |
O3A—S1A—O1A—K1 | 118.15 (8) | O6C—S1C—C1C—C2C | 147.2 (8) |
O2A—S1A—O1A—K1 | −7.61 (9) | O4C—S1C—C1C—C2C | 26.9 (7) |
C1A—S1A—O1A—K1 | −124.01 (7) | O5C—S1C—C1C—C2C | −90.2 (7) |
K2—S1A—O1A—K1 | 47.27 (7) | O1C—S1C—C1C—C2C | 1.15 (19) |
O2B—S1B—O1B—K3 | −113.15 (9) | O2C—S1C—C1C—C2C | −119.97 (17) |
O3B—S1B—O1B—K3 | 14.94 (11) | O3C—S1C—C1C—C2C | 121.98 (17) |
C1B—S1B—O1B—K3 | 130.29 (8) | K4—S1C—C1C—C2C | 177.73 (12) |
K4—S1B—O1B—K3 | −99.83 (7) | K3—S1C—C1C—C2C | 89.32 (15) |
O2B—S1B—O1B—K4 | −13.32 (9) | O6C—S1C—C1C—C6C | −34.6 (8) |
O3B—S1B—O1B—K4 | 114.77 (7) | O4C—S1C—C1C—C6C | −154.9 (7) |
C1B—S1B—O1B—K4 | −129.88 (7) | O5C—S1C—C1C—C6C | 87.9 (7) |
K3—S1B—O1B—K4 | 99.83 (7) | O1C—S1C—C1C—C6C | 179.31 (16) |
O3—S1—O2—K1 | 93.56 (19) | O2C—S1C—C1C—C6C | 58.20 (18) |
O1—S1—O2—K1 | −34.5 (2) | O3C—S1C—C1C—C6C | −59.85 (18) |
C1—S1—O2—K1 | −149.16 (17) | K4—S1C—C1C—C6C | −4.11 (17) |
K2—S1—O2—K1 | 102.90 (19) | K3—S1C—C1C—C6C | −92.51 (15) |
O3—S1—O2—K2 | −9.33 (8) | C6—C1—C2—C3 | −1.4 (3) |
O1—S1—O2—K2 | −137.39 (7) | S1—C1—C2—C3 | 174.55 (14) |
C1—S1—O2—K2 | 107.94 (7) | C6A—C1A—C2A—C3A | 1.3 (3) |
O1A—S1A—O2A—K2 | 101.94 (8) | S1A—C1A—C2A—C3A | −177.25 (14) |
O3A—S1A—O2A—K2 | −25.82 (9) | C6B—C1B—C2B—C3B | −0.8 (3) |
C1A—S1A—O2A—K2 | −141.32 (7) | S1B—C1B—C2B—C3B | 177.75 (14) |
K1—S1A—O2A—K2 | 94.92 (6) | C6C—C1C—C2C—C3C | −0.6 (3) |
O1A—S1A—O2A—K1 | 7.03 (9) | S1C—C1C—C2C—C3C | 177.50 (13) |
O3A—S1A—O2A—K1 | −120.74 (7) | C1—C2—C3—C4 | 0.4 (3) |
C1A—S1A—O2A—K1 | 123.77 (7) | C1A—C2A—C3A—C4A | 0.2 (3) |
K2—S1A—O2A—K1 | −94.92 (6) | C1B—C2B—C3B—C4B | −0.1 (3) |
O3B—S1B—O2B—K4v | 62.58 (19) | C1C—C2C—C3C—C4C | −0.7 (3) |
O1B—S1B—O2B—K4v | −171.33 (15) | C2—C3—C4—C5 | 1.0 (3) |
C1B—S1B—O2B—K4v | −55.38 (19) | C2—C3—C4—N1 | −179.85 (16) |
K4—S1B—O2B—K4v | 172.7 (2) | N2—N1—C4—C3 | −179.97 (16) |
K3—S1B—O2B—K4v | 137.35 (14) | N2—N1—C4—C5 | −0.9 (3) |
O3B—S1B—O2B—K4 | −110.12 (10) | C2A—C3A—C4A—C5A | −1.6 (3) |
O1B—S1B—O2B—K4 | 15.96 (10) | C2A—C3A—C4A—N1A | 179.28 (17) |
C1B—S1B—O2B—K4 | 131.92 (7) | N2A—N1A—C4A—C5A | 178.53 (16) |
K3—S1B—O2B—K4 | −35.35 (9) | N2A—N1A—C4A—C3A | −2.4 (3) |
O2—S1—O3—K3 | −156.23 (11) | C2B—C3B—C4B—C5B | 1.0 (3) |
O1—S1—O3—K3 | −27.45 (15) | C2B—C3B—C4B—N1B | 179.82 (17) |
C1—S1—O3—K3 | 86.33 (13) | N2B—N1B—C4B—C5B | −179.28 (16) |
K2—S1—O3—K3 | −167.08 (16) | N2B—N1B—C4B—C3B | 1.8 (3) |
O2—S1—O3—K2 | 10.85 (9) | C2C—C3C—C4C—C5C | 1.2 (3) |
O1—S1—O3—K2 | 139.64 (7) | C2C—C3C—C4C—N1C | −179.76 (16) |
C1—S1—O3—K2 | −106.59 (8) | N2C—N1C—C4C—C5C | −179.89 (16) |
O1A—S1A—O3A—K2 | −104.72 (7) | N2C—N1C—C4C—C3C | 1.0 (3) |
O2A—S1A—O3A—K2 | 21.89 (8) | C3—C4—C5—C6 | −1.3 (3) |
C1A—S1A—O3A—K2 | 137.24 (7) | N1—C4—C5—C6 | 179.62 (17) |
K1—S1A—O3A—K2 | −44.44 (7) | C3A—C4A—C5A—C6A | 1.7 (3) |
O2B—S1B—O3B—K3 | 114.97 (8) | N1A—C4A—C5A—C6A | −179.15 (16) |
O1B—S1B—O3B—K3 | −11.87 (8) | C3B—C4B—C5B—C6B | −0.9 (3) |
C1B—S1B—O3B—K3 | −126.84 (7) | N1B—C4B—C5B—C6B | −179.90 (16) |
K4—S1B—O3B—K3 | 59.70 (7) | C3C—C4C—C5C—C6C | −0.4 (3) |
O2C—S1C—O1C—K2 | −150.2 (3) | N1C—C4C—C5C—C6C | −179.56 (16) |
O3C—S1C—O1C—K2 | −24.1 (3) | C4—C5—C6—C1 | 0.3 (3) |
C1C—S1C—O1C—K2 | 92.7 (3) | C2—C1—C6—C5 | 1.1 (3) |
K4—S1C—O1C—K2 | −83.3 (3) | S1—C1—C6—C5 | −174.87 (14) |
K3—S1C—O1C—K2 | −24.8 (3) | C4A—C5A—C6A—C1A | −0.2 (3) |
O1C—S1C—O2C—K4 | 126.88 (9) | C2A—C1A—C6A—C5A | −1.2 (3) |
O3C—S1C—O2C—K4 | −0.33 (10) | S1A—C1A—C6A—C5A | 177.32 (14) |
C1C—S1C—O2C—K4 | −115.57 (7) | C4B—C5B—C6B—C1B | 0.0 (3) |
K3—S1C—O2C—K4 | 32.34 (10) | C2B—C1B—C6B—C5B | 0.8 (3) |
O1C—S1C—O3C—K3 | −1.26 (17) | S1B—C1B—C6B—C5B | −177.75 (14) |
O2C—S1C—O3C—K3 | 126.05 (13) | C4C—C5C—C6C—C1C | −0.9 (3) |
C1C—S1C—O3C—K3 | −118.63 (12) | C2C—C1C—C6C—C5C | 1.4 (3) |
K4—S1C—O3C—K3 | 125.70 (15) | S1C—C1C—C6C—C5C | −176.79 (14) |
O1C—S1C—O3C—K4 | −126.95 (9) | N1—N2—C7—C12 | −179.85 (16) |
O2C—S1C—O3C—K4 | 0.35 (11) | N1—N2—C7—C8 | −0.9 (2) |
C1C—S1C—O3C—K4 | 115.67 (8) | N1A—N2A—C7A—C8A | −179.35 (16) |
K3—S1C—O3C—K4 | −125.70 (15) | N1A—N2A—C7A—C12A | −0.5 (3) |
O6C—S1C—O4C—K2 | 145 (3) | N1B—N2B—C7B—C8B | −177.56 (16) |
O5C—S1C—O4C—K2 | 10 (3) | N1B—N2B—C7B—C12B | 2.8 (3) |
C1C—S1C—O4C—K2 | −100 (3) | N1C—N2C—C7C—C8C | −179.80 (16) |
K4—S1C—O4C—K2 | 112 (3) | N1C—N2C—C7C—C12C | 1.4 (3) |
K3—S1C—O4C—K2 | 145 (3) | C12—C7—C8—C9 | −1.7 (3) |
O6C—S1C—O4C—K3 | 0.0 (9) | N2—C7—C8—C9 | 179.36 (16) |
O5C—S1C—O4C—K3 | −135.2 (6) | C12A—C7A—C8A—C9A | 2.0 (3) |
C1C—S1C—O4C—K3 | 114.7 (3) | N2A—C7A—C8A—C9A | −179.08 (16) |
K4—S1C—O4C—K3 | −33.8 (8) | C12B—C7B—C8B—C9B | −2.7 (3) |
O4C—S1C—O6C—K4 | −121.5 (11) | N2B—C7B—C8B—C9B | 177.61 (16) |
O5C—S1C—O6C—K4 | 11.3 (15) | C12C—C7C—C8C—C9C | −1.6 (3) |
C1C—S1C—O6C—K4 | 123.4 (10) | N2C—C7C—C8C—C9C | 179.58 (16) |
K3—S1C—O6C—K4 | −121.5 (13) | C7—C8—C9—C10 | 0.7 (3) |
O4C—S1C—O6C—K3 | 0.0 (10) | C7A—C8A—C9A—C10A | −0.1 (3) |
O5C—S1C—O6C—K3 | 132.8 (6) | C7B—C8B—C9B—C10B | 0.6 (3) |
C1C—S1C—O6C—K3 | −115.1 (4) | C7C—C8C—C9C—C10C | 0.4 (3) |
K4—S1C—O6C—K3 | 121.5 (13) | C8—C9—C10—C11 | 0.4 (3) |
C4—N1—N2—C7 | 179.35 (14) | C8—C9—C10—N3 | −178.37 (17) |
C4A—N1A—N2A—C7A | 179.46 (15) | C8A—C9A—C10A—N3A | 175.81 (17) |
C4B—N1B—N2B—C7B | −179.25 (14) | C8A—C9A—C10A—C11A | −1.8 (3) |
C4C—N1C—N2C—C7C | −178.85 (14) | C8B—C9B—C10B—N3B | −175.77 (17) |
O2—S1—C1—C2 | 20.81 (17) | C8B—C9B—C10B—C11B | 1.7 (3) |
O3—S1—C1—C2 | 141.83 (15) | C8C—C9C—C10C—C11C | 0.8 (3) |
O1—S1—C1—C2 | −99.54 (15) | C8C—C9C—C10C—N3C | −177.53 (17) |
K2—S1—C1—C2 | 88.45 (15) | C9—C10—C11—C12 |