Microbatch under-oil salt screening of organic cations: single-crystal growth of active pharmaceutical ingredients

Multicomponent solid forms of active pharmaceutical ingredients represent a modern method of tuning their physicochemical properties. Typically, salts are the most commonly used multicomponent solid form in the pharmaceutical industry. More than 38% are formulated as organic cations. Salt screening is an essential but demanding step when identifying the most appropriate formulation. The microbatch under-oil crystallization technique of proteins has been combined with the previously developed high-throughput vapour-diffusion screening for use as a novel method of primary salt screening of organic cations. The procedure allows the set up of about 100 crystallization experiments per 30 min. This requires between 17 and 564 mg of screened cationic active pharmaceutical ingredients, which were of moderate to very high water solublity. Five distinct organic salts, three of them diverse active pharmaceutical compounds or the other enantiomer thereof, in the form of chloride salts were tested. The screening was extremely successful; at least two new single-crystal structures could be obtained for each particular compound and many more salts as single crystals were formed compared with our previous vapour-diffusion method.

1. Introduction

Control over the multicomponent solid form of an active pharmaceutical ingredient (API) is a modern way of improving physicochemical properties of the API without changing its core chemical structure (Schultheiss & Newman, 2009). Nowadays, pharmaceutical salts are the most frequently used in multicomponent form in a final drug formulation, corresponding to about 50% of all solid APIs. Positively charged APIs occur in 38% of those FDA approved drugs (prior to the end of 2006), in which the drug has a molecular weight less than 1000 Da (Paulekuhn et al., 2007). The widely used chloride is increasingly replaced with other anions (Paulekuhn et al., 2007). The motivation for this development is based on, for example, lower hygroscopicity or targeting that part of the gastrointestinal tract where the salt will be the most soluble (Berge et al., 1977). The choice of salt is a standard part of any preformulation study (Morissette et al., 2004). Furthermore, salts other than chlorides can be helpful during the purification of a product.

The standard salt screenings are time, material and labour intensive. New forms are normally generated by direct ionization of the APIs (Morissette et al., 2004; Tamura et al., 2018). Surprisingly, to the best of our knowledge, only one method of high-throughput salt screening using ion exchange has been published (Nievergelt et al., 2018). It is a modification of the vapour-diffusion crystallization method (VDHT) originally developed and optimized for macromolecules (McPherson & Gavira, 2014). In the method developed by us (Nievergelt et al., 2018), a water-soluble organic cationic salt (normally in chloride form) is mixed with a water-soluble sodium or potassium salt to generate a new, less water-soluble salt of the organic cation with a new anion. Another feasible modification of the crystallization procedure is microbatch under-oil crystallization (Chayen et al., 1992). The biggest advantage of under-oil crystallization compared with the vapour-diffusion method is the higher level of concentration that can be achieved (see Fig. S1 of the supporting information). The vapour-diffusion method achieves supersaturation by equalization of the water vapour pressure between two different solutions. The first solution (the drop in which the crystallization shall take place) is normally a 1:1 mixture of the stock solution of the screened cationic API and the stock solution of the anion. The second one is a pure stock solution of the anion. The water activity in the drop is approximately twice that of the anion stock solution, as this solution has been one-time diluted by addition of the aqueous solution of the organic cation. Having a small drop and a huge reservoir with the stock solution of the anion, which both share the same vapour phase, the final concentration of the organic cation within the drop will reach approximately twice the starting concentration. In contrast, under-oil screening achieves supersaturation by slow penetration of water through the silicone oil (Fig. S1 of the supporting information). Hence, the screened drop is slowly concentrated until an almost dry residue is obtained. Moreover, microbatch under-oil crystallization can be performed with standard laboratory equipment such as multichannel pipettes and crystallization plates without the need for pipetting robots. On the other hand, one could use a robot for setting up the crystallization plates as has already been done in the field of protein crystallization (Chayen et al., 1990; McPherson & Gavira, 2014). Furthermore, using different vessels, this method might also be upscalable. Note that the probability of crystallizing one of the starting materials during under-oil crystallization is higher, rendering the evaluation more difficult (Baldock et al., 1996).

In this work, we investigated the crystallization of five organic cations (Fig. 1), two of which are APIs. R,S-carnitine­nitrile chloride and R-carnitine­nitrile chloride {[(±)-Car]Cl and [(−)-Car]Cl} are precursors in the synthesis of carnitine or its derivatives. Carnitine is used in the treatment of different diseases from neurological problems to diabetes mellitus. Only the crystal structure of the tetra­phenyl­borate salts of [(±)-Car]⁺ and [(−)-Car]⁺ have been reported previously (Nievergelt et al., 2018). (1S,2R)-(+)-Ephedrine hydro­chloride ([(+)-EphH]Cl) is the other enantiomer of the naturally occurring (1R,2S)-(−)-ephedrine, which is employed for the treatment of bronchial asthma and emphysema. (1S,2R)-(+)-Ephedrine is, in general, pharmacologically inactive compared with its other enantiomer (Lee, 2011). There are many structures of salts of the various diastereomers of ephedrine (Collier et al., 2006; Wu et al., 2012) described in the Cambridge Structural Database (Groom et al., 2016). Diltiazem hydro­chloride ([DilH]Cl) is a well known calcium channel blocking agent, which is used for the treatment of stable angina pectoris and hypertension. Five crystal structures containing diltiazem have been reported and four of them are salts (Kojić-Prodić et al., 1984; Tanaka et al., 1992; Stepanovs et al., 2016). Trazodone hydro­chloride ([TrH]Cl) is being used pharmaceutically as an antidepressant (Davidoff et al., 1987). The crystal structures of the protonated trazodone chloride (Fillers & Hawkinson, 1979), iodide and oxalate (Nievergelt et al., 2018) salts have been reported previously.

Figure 1 Chemical structures of the screened organic cations in the form of chlorides or hydro­chlorides.

2. Experimental

(1S,2R)-(+)-Ephedrine hydro­chloride and trazodone hydro­chloride were obtained from Sigma–Aldrich. R-Carnitine­nitrile chloride was obtained from Angene Chemical, Hong Kong, HK. R,S-Carnitine­nitrile chloride was obtained from Frontier Scientific, Logan, UT, USA. Diltiazem hydro­chloride was provided by Zentiva k.s., Prague, CZ. The used silicone oil (unless otherwise noted) was article number 146153 from Sigma–Aldrich; it has a viscosity of 50 cSt (1 cSt = 1 mm² s⁻¹) and is normally used for melting-point and boiling-point apparatus. This oil was previously used in under-oil screenings of proteins (Vetting et al., 2009). For a few experiments, a silicone oil with a much lower viscosity of 5 cSt was employed (article number: 317667 from Sigma–Aldrich). Sodium or potassium salts of suitable counterions were obtained from various commercial suppliers. The reason for choosing either a sodium or potassium salt was based on the accessibility of one versus the other (e.g. sodium hydrogen phthalate is not commercially available, however, its potassium salt is). In cases when the sodium or potassium salts were not commercially available, the sodium salts were prepared by titration of the corresponding acids with a sodium hydroxide solution (2M) until a pH of 7 was reached. The solutions of the newly prepared salts were concentrated with the help of a rotary evaporator and dried by lyophilization. The water content was determined by elemental analysis (carbon, hydrogen and nitro­gen) of each new salt. The concentrations of the anion solutions were chosen such that they were about half saturated. In the case of high concentrations, lower concentrations of the same anion were also employed in order to test the influence of the concentration of the anions.

The screening technique described in this publication combines the primary salt screening of APIs and growing single crystals of hits. Silicone oil (100 µl) was added to each well in a 96 round bottom well costar 3795 plate (Corning Incorporated, USA). Stock solutions of four organic cations including two APIs [diltiazem hydro­chloride, (R,S)-carnitine­nitrile chloride, (R)-carnitine­nitrile chloride, (1S,2R)-(+)-ephedrine hydro­chloride, 5 µl each; 90% maximal saturation in water] were pipetted with the help of an eight-channel pipette directly into the silicone oil within the wells. The drops of these aqueous solutions sank to the bottom of the well. Afterwards, individual stock solutions of the counterions (5 µl) were added to each well with silicone oil and the to-be-crystallized organic cation. When trying different volumes of solutions, volumes smaller than 5 µl of the concentrated anion solutions were difficult to pipette due to their high viscosity, yet volumes larger than 5 µl of the analyte were actually superfluous and wasted stock solutions. In some cases, it was necessary to combine two separate aqueous drops with a pipette tip under oil in order to have one common drop. In every well, there must be just one drop of the mixture, which is crucial for the under-oil experiment. Initial screenings were carried out for 147 different conditions with 86 different counterions (Table S1).

In a second series of experiments, we concentrated on ephedrine and trazodone as well as on 96 promising anion solutions (see Table S2). Ephedrine is known to form many salts (Collier et al., 2006), some of which we did not obtain with our first series of experiments. Secondly, all studied cations of the first series were highly soluble or even extremely soluble in water. In order to have a compound that also displays moderate but not too high solubility in water, we selected trazodone hydro­chloride, which we had studied in our previous vapour-diffusion investigation (Nievergelt et al., 2018). Compared with the 147 conditions used previously, we eliminated anions that were only soluble at millimolar concentrations (e.g. sodium do­decyl­sulfate) or whose solution became black because of lack of chemical stability (sodium 4-amino­salicylate). Furthermore, the chosen maximum concentration of the anion salt should approximately correspond to a half-saturated solution of the salt of that very anion. Therefore, some of the initial concentrations of the sodium or potassium salts were increased as we discovered that these concentrations had been well below half-saturation in our first series of experiments. Additionally, we used smaller volumes of the organic cation solution compared with the volumes of the anion solutions in order to promote anion exchange. For ephedrine, we mixed 2 µl of 90% saturated ephedrine solution and 20 µl of counterion solution. For trazodone, we mixed 4 µl of 90% saturated trazodone solution and 10 µl of counterion solution. We monitored all wells essentially every day for 30 days and marked the outcome of the crystallizations. Promising looking crystals were isolated and placed in Infineum V8512 oil as soon as possible as the solutions continued to become more concentrated. In some cases, it was necessary to induce crystal growth by scratching the wells with a dissecting needle.

Single-crystal X-ray diffraction patterns were measured on a Rigaku-Oxford Diffraction XtaLAB Synergy-S dual source diffractometer: Kappa-axis four-circle goniometer with a Dectris Pilatus3 R 200 K hybrid pixel area detector and Cu and Mo PhotonJet microfocus X-ray sources. The data collection strategy and data reduction were performed using CrysAlisPRO (Rigaku Oxford Diffraction, 2015). Crystals were fished out using a micro-spoon spatula from Bochem (35781 Weilburg, Germany, article number 3344) also available at VWR (article number 231–1355). The crystals were prepared on a glass slide under Infineum V8512 oil and the single crystals were mounted on top of a 18 mm Mounted CryoLoop in a CrystalCap Magnetic (Hampton Research). The structures were solved using SUPERFLIP (Palatinus & Chapuis, 2007), SIR92 (Altomare et al., 1994) or SHELXT (Sheldrick, 2015a), and were refined in CRYSTALS (Betteridge et al., 2003) or SHELXL2014 (Sheldrick, 2015b). Graphical output was made with the help of Mercury (Macrae et al., 2008).

3. Results and discussion

Protein micro-batch crystallization (Chayen et al., 1992) was modified to be used for the salt screening of organic cations. Initially, we chose four different organic cations for the screening, two permanent cations [(R,S)-carnitine­nitrile chloride and (R)-carnitine­nitrile chloride] and two bases as their hydro­chloride salts [diltiazem hydro­chloride and (1S,2R)-(+)-ephedrine hydro­chloride]. Their approximate solubilities are given in Table 1. Initial screenings were carried out for 147 different conditions with 86 different counterions (Table S1). The chosen anions were selected to include many diverse inorganic and organic anions, many of them fulfilling the GRAS condition (Select Committee on GRAS Substances, 2017), some of them were selected because of their propensity to form crystalline salts. As we have found previously (Nievergelt et al., 2018) that half-saturated anion solutions work well, we also employed them here. The concentration of some selected anion solutions with concentrations higher than 2M were halved once or twice in order to promote crystal growth rather than a powdery precipitate. As the initially chosen compounds (carnitine­nitrile chloride, diltiazem and ephedrine hydro­chloride) all exhibited rather high solubility and only formed new crystal salts in the presence of highly concentrated anions, we set up a second round of optimization. First, we changed the volume ratio of cation solution to anion solution in the case of ephedrine from 1:1 to 1:10 in order to promote the anion exchange. Secondly, we selected an additional API, trazodone, that we had already tested in the vapour-diffusion nano-crystallization technique (Nievergelt et al., 2018) and that has a 10× lower aqueous solubility than ephedrine, the organic salt with the lowest solubility in the current study so far (Table 1). For trazodone, we chose an API to anion solution volume ratio of 1:2.5. Finally, we reduced the number of crystallization trials per analyte in order to efficiently use 96 well plates (for details, see the Experimental).

Table 1
Screened cations and their aqueous solubility at 22°C

	Approximate solubility (mg ml^−1)	Amount needed (mg)†	Solution molarity [M]‡
Diltiazem hydro­chloride	720 ± 70§	312	1.44
(R,S)-Carnitine­nitrile chloride	1120 ± 106¶	486	5.64
(R)-Carnitine­nitrile chloride	1300 ± 200¶	564	6.54
(1S,2R)-(+)-Ephedrine hydro­chloride	257± 1¶	111	1.15
Trazodone hydro­chloride	38.5 ± 0.2¶	17	0.085

†For screening 97 conditions.
‡At 90% saturation.
§Determined as described by Nievergelt et al. (2018).
¶Value taken from the work by Nievergelt et al. (2018).

The formation of single crystals of the organic cation together with an anion other than chloride (if present) was selected as the desired endpoint of the crystallization trials. The positive results of the crystallization experiments, including the concentration of the counterion solution used, are summarized in Table 2. Additionally, the number of the day on which crystals were first observed is given (e.g. D0: crystals observed on the day of setting up the experiment). We have succeeded in the crystallization of at least two salts for each screened cation. In three cases, we observed crystallization of a supersaturated solution directly after having touched the drop with a spatula or scratched the well with a dissecting needle. The resulting crystals were the new bromide (see Fig. 2), tetra­fluoro­borate and iodide salts of [(−)-Car]⁺ as well as the iodide salt of [(±)-Car]⁺. Furthermore, there were three positive hits with too low-quality crystals for structural analysis of [(±)-Car] bromide, [(±)-Car] tetra­phenyl­borate and [(−)-Car] tetra­phenyl­borate. Moreover, we succeeded in the crystallization of four new salt forms of diltiazem (see Fig. 2). The diltiazem crystal structures of the bromide, the iodide and the nitrate salts are essentially isostructural with the published data on the chloride salt (Kojić-Prodić et al., 1984). Additionally, we tried to crystallize the pure solution of the screened cations in the forms of chlorides or hydro­chlorides using the under-oil technique. In this way, the unit cells of the crystals of the [DilH]Cl and [(+)-EphH]Cl salts were found to correspond to the known forms of the hydro­chlorides. [(−)-Car]Cl crystallized as high-quality single crystals. Surprisingly, R,S-carnitine­nitrile chloride crystallized with two S-carnitine­nitrile and one R-carnitine­nitrile cations in the asymmetric unit of the chiral space group P2₁. Such a rare system has been described in the literature either as a pseudo unbalanced crystallization, co-crystals of a racemate or unbalanced chiral packing (Fábián & Brock, 2010; Albrecht et al., 2010; Wachter et al., 2016; Kotelnikova et al., 2017; Grothe et al., 2017). The remaining observed negative crystallization results were either mixtures of NaCl (Fig. S2) and amorphous residue, amorphous residue only or pure chlorides (or hydro­chlorides) of the tested anions.

Table 2
Obtained single crystals

Crystals were grown by mixing 5 µl of the organic cation solution and 5 µl of the anion solution unless otherwise noted. DX: crystals were observed after X days.

Salt providing the new anion	Molarity	[(+)-EphH]Cl	[(−)-Car]Cl	[(±)-Car]Cl	[DilH]Cl	[TrazH]Cl
Sodium bromide	4.08	D0†	D14‡		D5
Sodium iodide	5.34	D5†	D8‡	D11	D6	D1†, §
Sodium tetra­fluoro­borate	2.00		D10¶			D3§
Potassium thio­cyanate	7.34	D2†				D1§
Sodium nitrate	4.61	D30‡, ††, ‡‡			D6	D1§
Sodium di­hydrogen phosphate	3.40				D5
Sodium pyrrolidone carboxyl­ate	4.96	D1††
Sodium benzene­sulfonate	1.10	D16†, ††
Disodium oxalate	0.138	D6†, ††				D1†, §
Disodium malonate	2.97	D16†, ††
Sodium L-malate	2.92	D30††
Potassium sodium L-tartrate	1.40	D30††
No additional salt added		D15†	D14	D7	D6†

†Published structure, sometimes of the other enantiomer (Hearn & Bugg, 1972; Kojić-Prodić et al., 1984; Collier et al., 2006; Wu et al., 2012; Nievergelt et al., 2018).
‡Crystallized after touching the drop with a spatula or scratching the well with a dissecting needle.
§Obtained by mixing 4 µl of the trazodone solution and 10 µl of the anion solution.
¶Concentration of sodium tetra­fluoro­borate was 4.0M.
††Obtained by mixing 2 µl of the ephedrine solution and 20 µl of the anion solution.
‡‡Two polymorphs (I† and II) observed.

Figure 2 Left: displacement ellipsoid representation of [DilH][NO3]. Right: displacement ellipsoid representation of [(−)-Car]Br. Ellipsoids are depicted at 50% probability.

As a next step for improving the under-oil method, we employed a larger volume of anion solution compared with the analyte solution. This increases the anion to organic cation ratio and therefore was predicted to favour the formation of the new salt. Finally, we reduced the number of anion solutions to just 96 selected conditions (ignoring the salt free condition), allowing one series of screening experiments to be carried out in just one 96 well plate. We eliminated anions with a low millimolar solubility that would not promote a quantitative anion exchange and anions that were determined to be unstable in an aqueous, aerated solution [such as sodium 4-amino­salicylate (The Merck Index, 1976)]. Indeed, the improved method yielded five salts of trazodone, of which three were novel. The second round of crystallization of ephedrine with a 1:10 volumetric ratio of analyte solution versus anion solution gave seven additional salts, of which four were new. One of the novel structures was a new polymorph of ephedrinium nitrate, which crystallized in the chiral space group P2₁ with two formula units in the asymmetric unit and unit-cell dimensions of a = 6.0401 (3), b = 29.3553 (8), c = 7.3828 (3) Å, β = 112.806 (5)° and V = 1206.70 (9) ų. Later, three-dimensional crystals (Fig. S15) were produced that were identified as the known nitrate salt polymorph I (Collier et al., 2006), which also crystallized in the monoclinic space group P2₁, but with just one formula unit in the asymmetric unit and with unit-cell dimensions of a = 5.536 (5) Å, b = 6.839 (9) Å, c = 15.669 (12) Å, β = 97.28 (7)° and V = 588 (1) ų. In polymorph I, the ephedrine cation adopts a folded conformation, while in polymorph II it is in an extended conformation. Further anions that formed novel crystal structures with ephedrine, are L-tartrate, which crystallizes as a monohydrate in the chiral space group P2₁. The trihydrate has previously been reported by Collier et al. (2006). Additionally, we succeeded in crystallizing the monohydrate of L-malate; its anhydrate form has been described again by Collier. For trazodone, three novel crystal structures of its protonated form with either nitrate, tetra­fluoro­borate or thio­cyanate could be determined. For all wells in which no crystallization could be observed, the drops were punctured with a spatula or the wells below the drops scratched with a preparation needle. Since in a few cases, crystal growth in some over-saturated drops could be observed after this procedure, we recommend performing this easy step for all wells in which no crystals have formed after a few weeks.

In order to study the influence of the ratio of anion to organic cation, the cation of the salt that provides the final anion and the used oil, we performed detailed design experiments for two selected anions, iodide and oxalate (Tables S3 and S4). For the crystallization of ephedrinium iodide, the ratio of ephedrinium to iodide was varied between 1 and 200. Additionally, lithium, sodium and potassium iodide at the same concentration were compared in order to assess their influence on the crystallization of ephedrinium iodide. And thirdly, the whole series was repeated with a silicone oil possessing a 10× lower viscosity (5 cSt) than the one previously used, as d'Arcy and co-workers have shown that the viscosity of the silicone oil more or less linearly correlates with the time it takes for the protein crystals to appear (D'Arcy et al., 1996). The summary of our results of the crystallization of ephedrinium iodide (Table S3) is as follows. Crystals were observed within a 5- to 50-fold ratio of iodide to ephedrinium. At a ratio smaller than 5, there seems to be insufficient excess iodide present. At a ratio higher than 50, there was not enough ephedrinium in the drops. While small differences could be noticed, no clear effects of the cation of the iodide salt nor the used silicone oil could be established. For the crystallization of bis-ephedrinium oxalate (Table S4), the influence of the ratio of oxalate to ephedrinium and the used silicone oil was studied. The growth of ephedrinium oxalate crystals could be observed over a wide ratio between 0.01 and 3.3 up to 33.3 (depending on the oil used). If the ratio of oxalate to ephedrinium was 0.1 or lower, after a number of days the remaining ephedrinium chloride formed large crystals in both oils.

As a final step, we compared the results of the under-oil microbatch screening with the VDHT technique (Nievergelt et al., 2018). The chosen cations for the comparison were [(−)-Car]⁺, [(±)-Car]⁺, [(+)-EphH]⁺ and [TrazH]⁺ with decreasing solubilities in this order (see Tables 1 and 3). The under-oil microbatch screening was able to produce many more crystalline salts with an exchanged anion than with the VDHT screening for any of the four compared cations (see Table 3). The reason for the superior performance of the under-oil method most likely lies in the higher supersaturation that can be achieved with the under-oil method compared with vapour diffusion.

Table 3
Comparison of the results obtained by under-oil and vapour-diffusion (VDHT) methods

(×): no salt crystal was obtained during the screening. Abbreviations: tetra­phenyl­borate: [TPB]⁻; thio­cyanate: [SCN]⁻; oxalate: [OXA]²⁻; benzene­sulfonate [BS]⁻; pyrrolidone carboxyl­ate: [Pyrcarb]⁻.

Cation to be crystallized	[(+)-EphH]^+		[(−)-Car]^+		[(±)-Car]^+		[TrazH]Cl
Method	Under oil	VDHT	Under oil	VDHT	Under oil	VDHT	Under oil	VDHT
Anions	Cl^−	Cl^−	[TPB]^−	[TPB]^−	[TPB]^−	[TPB]^−	I^−	I^−
	Br^−	Br^−	Cl^−	×	Cl^−	×	[OXA]^2−	[OXA]^2−
	I^−	I^−	Br^−	×	Br^−	×	NO3^−	×
	[SCN]^−	[SCN]^−	I^−	×	I^−	×	[BF4]^−	×
	[OXA]^2−	[OXA]^2−	[BF4]^−:Cl^−	×			[SCN]^−	×
	NO3^−†	×
	[BS]^−	×
	[Malonate]^2−	×
	[L-Malate]^2−	×
	[L-Tartrate]^2−	×
	[Pyrcarb]^−	×

†Two polymorphs obtained.

When analysing the results of our crystallizations, it became clear that mainly anions that were present in equally high or higher concentrations than the organic cations, crystallized together with them. The only anion that does not follow this rule is oxalate. This is in accordance with a report by Stepanovs and co-workers, who described a system also containing a methyl­ammonium ethanol unit. The oxalate salt of propranolol had a 28-fold lower aqueous solubility of the organic cation when compared with the chloride salt (Stepanovs et al., 2015). Additionally, we compared the success rate of the under-oil technique with the classical titration method. Davey and co-workers (Collier et al., 2006) report the synthesis and crystallization of 16 salt forms starting from the free base ephedrine and adding one or half of an equivalent of acid or diacid. Three different solvents were employed for the synthesis and subsequent crystal growth. Our direct approach with the optimized procedure starting from one single solution of ephedrinium chloride directly yielded single crystals of eleven salt forms apart from the starting chloride salt. Four of them had novel crystal structures, including one new polymorph of ephedrinium nitrate.

4. Conclusions

The under-oil crystallization technique for proteins was successfully adapted for use in salt screening of APIs. After an optimization procedure, the ideal screening involves 96 crystallization batches that consume less than 200 µl of a 90% saturated solution for each screened API and the experiment can be set up within ca 30 min. For each screened cation, we could determine the single-crystal structure of at least two new salts, each one with a different anion. Five salts of [DilH]⁺ and twelve salts of [(+)-EphH]⁺ were observed and their crystals grew in sufficient quality for single-crystal X-ray determination (SCXRD). Two of the four observed crystals of salts of [(±)-Car]⁺ and four of the five of [(−)-Car]⁺ crystallized in sufficient quality for SCXRD. To the best of our knowledge, this is the first application of the microbatch under-oil crystallization technique for the crystal growth of small molecules. Finally, the under-oil screening was compared to the vapour-diffusion method. The under-oil method was found to be much more effective in generating single crystals for all five compounds, which were crystallized by both methods (Table 3). Additionally, the under-oil technique does not require the use of an expensive pipetting robot. In total, 17 new salts of the studied five cations were prepared. On the other hand, the under-oil technique consumes a little more material because the individual experiment requires a higher volume of analyte solution of between 2 and 5 µl rather than 100 nl in the vapour-diffusion experiment performed by the liquid handling robot. As a final remark, we note that the under-oil technique favours the crystallization of any kind of water-soluble substance from aqueous solutions.

5. Related literature

The following references are cited in the supporting information: Prince (1982); Watkin (1994).

Supporting information

Computing details

Data collection: SuperNova, (Oxford Diffraction, 2010) for RScarnitinenitrilechloride, RScarnitinenitrileiodide, Rcarnitinenitrilechloride, Rcarnitinenitrilebromide, Rcarnitinenitrileiodide, Rcarnitinenitrile2tetrafluoroborate1chloride1, Diltiazembromide, Diltiazemiodide, Diltiazemnitrate, Diltiazemphosphatesesquihydrate; CrysAlis PRO 1.171.39.46 (Rigaku OD, 2018) for pn180815_uo_eph_1_180814_pyrolidcarbox, pn180815_uo_traz_1_180814_c6_nitrate_mo, pn180815_uo_traz_1_180814_scn, pn180817_uo_trh_1_180814_b1_bf4, pn180830_uo_eph_1_180814_b12_benzsulf, pn180914_uo_eph_1_180814_g5_tart, pn180914_uo_eph_2_180814_c6_scr2; CrysAlis PRO 1.171.40.16c (Rigaku OD, 2018) for pn180914_uo_eph_1_180814_g4_2. Cell refinement: CrysAlis PRO, (Agilent, 2011) for RScarnitinenitrilechloride, Rcarnitinenitrilechloride, Rcarnitinenitrilebromide, Rcarnitinenitrileiodide, Rcarnitinenitrile2tetrafluoroborate1chloride1, Diltiazembromide, Diltiazemiodide, Diltiazemnitrate, Diltiazemphosphatesesquihydrate; CrysAlis PRO (Rigaku Oxford Diffraction, 2017) for RScarnitinenitrileiodide; CrysAlis PRO 1.171.39.46 (Rigaku OD, 2018) for pn180815_uo_eph_1_180814_pyrolidcarbox, pn180815_uo_traz_1_180814_c6_nitrate_mo, pn180815_uo_traz_1_180814_scn, pn180817_uo_trh_1_180814_b1_bf4, pn180830_uo_eph_1_180814_b12_benzsulf, pn180914_uo_eph_1_180814_g5_tart, pn180914_uo_eph_2_180814_c6_scr2; CrysAlis PRO 1.171.40.16c (Rigaku OD, 2018) for pn180914_uo_eph_1_180814_g4_2. Data reduction: CrysAlis PRO, (Agilent, 2011) for RScarnitinenitrilechloride, Rcarnitinenitrilechloride, Rcarnitinenitrilebromide, Rcarnitinenitrileiodide, Rcarnitinenitrile2tetrafluoroborate1chloride1, Diltiazembromide, Diltiazemiodide, Diltiazemnitrate, Diltiazemphosphatesesquihydrate; CrysAlis PRO (Rigaku Oxford Diffraction, 2017) for RScarnitinenitrileiodide; CrysAlis PRO 1.171.39.46 (Rigaku OD, 2018) for pn180815_uo_eph_1_180814_pyrolidcarbox, pn180815_uo_traz_1_180814_c6_nitrate_mo, pn180815_uo_traz_1_180814_scn, pn180817_uo_trh_1_180814_b1_bf4, pn180830_uo_eph_1_180814_b12_benzsulf, pn180914_uo_eph_1_180814_g5_tart, pn180914_uo_eph_2_180814_c6_scr2; CrysAlis PRO 1.171.40.16c (Rigaku OD, 2018) for pn180914_uo_eph_1_180814_g4_2. Program(s) used to solve structure: Superflip (Palatinus & Chapuis, 2007) for RScarnitinenitrilechloride, RScarnitinenitrileiodide, Rcarnitinenitrileiodide, Rcarnitinenitrile2tetrafluoroborate1chloride1, Diltiazembromide, Diltiazemnitrate, Diltiazemphosphatesesquihydrate; SIR92 (Altomare et al., 1994) for Rcarnitinenitrilechloride, Rcarnitinenitrilebromide, Diltiazemiodide; ShelXT (Sheldrick, 2015) for pn180815_uo_traz_1_180814_c6_nitrate_mo, pn180815_uo_traz_1_180814_scn, pn180817_uo_trh_1_180814_b1_bf4, pn180830_uo_eph_1_180814_b12_benzsulf. Program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003) for RScarnitinenitrilechloride, RScarnitinenitrileiodide, Rcarnitinenitrilechloride, Rcarnitinenitrilebromide, Rcarnitinenitrileiodide, Rcarnitinenitrile2tetrafluoroborate1chloride1, Diltiazembromide, Diltiazemiodide, Diltiazemnitrate, Diltiazemphosphatesesquihydrate; SHELXL (Sheldrick, 2015) for pn180815_uo_eph_1_180814_pyrolidcarbox, pn180815_uo_traz_1_180814_c6_nitrate_mo, pn180815_uo_traz_1_180814_scn, pn180817_uo_trh_1_180814_b1_bf4, pn180830_uo_eph_1_180814_b12_benzsulf, pn180914_uo_eph_1_180814_g4_2, pn180914_uo_eph_1_180814_g5_tart, pn180914_uo_eph_2_180814_c6_scr2. Molecular graphics: CAMERON (Watkin et al., 1996) for RScarnitinenitrilechloride, RScarnitinenitrileiodide, Rcarnitinenitrilechloride, Rcarnitinenitrilebromide, Rcarnitinenitrileiodide, Rcarnitinenitrile2tetrafluoroborate1chloride1, Diltiazembromide, Diltiazemiodide, Diltiazemnitrate, Diltiazemphosphatesesquihydrate; Olex2 (Dolomanov et al., 2009) for pn180815_uo_eph_1_180814_pyrolidcarbox, pn180815_uo_traz_1_180814_c6_nitrate_mo, pn180815_uo_traz_1_180814_scn, pn180817_uo_trh_1_180814_b1_bf4, pn180830_uo_eph_1_180814_b12_benzsulf, pn180914_uo_eph_1_180814_g4_2, pn180914_uo_eph_1_180814_g5_tart, pn180914_uo_eph_2_180814_c6_scr2. Software used to prepare material for publication: CRYSTALS (Betteridge et al., 2003) for RScarnitinenitrilechloride, RScarnitinenitrileiodide, Rcarnitinenitrilechloride, Rcarnitinenitrilebromide, Rcarnitinenitrileiodide, Rcarnitinenitrile2tetrafluoroborate1chloride1, Diltiazembromide, Diltiazemiodide, Diltiazemnitrate, Diltiazemphosphatesesquihydrate; Olex2 (Dolomanov et al., 2009) for pn180815_uo_eph_1_180814_pyrolidcarbox, pn180815_uo_traz_1_180814_c6_nitrate_mo, pn180815_uo_traz_1_180814_scn, pn180817_uo_trh_1_180814_b1_bf4, pn180830_uo_eph_1_180814_b12_benzsulf, pn180914_uo_eph_1_180814_g4_2, pn180914_uo_eph_1_180814_g5_tart, pn180914_uo_eph_2_180814_c6_scr2.

(RScarnitinenitrilechloride)

Crystal data

C7H15N2O·Cl	F(000) = 576
Mr = 178.66	Dx = 1.210 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 7637 reflections
a = 7.2588 (3) Å	θ = 3–33°
b = 8.9399 (4) Å	µ = 0.34 mm^−1
c = 22.7927 (9) Å	T = 183 K
β = 95.818 (4)°	Block, yellow
V = 1471.47 (11) Å^3	0.13 × 0.08 × 0.06 mm
Z = 6

Data collection

Oxford Diffraction SuperNova diffractometer	7769 reflections with I > 2.0σ(I)
Graphite monochromator	Rint = 0.032
ω scans	θmax = 32.6°, θmin = 2.5°
Absorption correction: multi-scan CrysAlisPro, (Agilent, 2011)	h = −10→10
Tmin = 0.77, Tmax = 0.98	k = −13→13
23769 measured reflections	l = −34→30
10401 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: difference Fourier map
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.052	Method = Modified Sheldrick w = 1/[σ^2(F^2) + ( 0.07P)^2 + 0.23P] , where P = (max(Fo^2,0) + 2Fc^2)/3
wR(F^2) = 0.128	(Δ/σ)max = 0.0004
S = 1.00	Δρmax = 0.75 e Å^−3
10401 reflections	Δρmin = −0.43 e Å^−3
299 parameters	Absolute structure: Flack (1983), 4756 Friedel-pairs
1 restraint	Absolute structure parameter: −0.03 (4)
Primary atom site location: Other

Special details

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1K.

Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.2393 (4)	0.4065 (3)	0.12418 (11)	0.0559
C2	0.2157 (3)	0.2895 (3)	0.10570 (9)	0.0342
C3	0.1838 (3)	0.1392 (3)	0.08215 (8)	0.0296
C4	0.1255 (3)	0.1376 (2)	0.01532 (8)	0.0257
O5	−0.03223 (19)	0.2299 (2)	0.00070 (6)	0.0340
C6	0.2840 (3)	0.1967 (2)	−0.01686 (8)	0.0252
N7	0.2810 (2)	0.1497 (2)	−0.08098 (7)	0.0241
C8	0.4525 (3)	0.2129 (3)	−0.10372 (10)	0.0325
C9	0.1145 (3)	0.2128 (3)	−0.11692 (8)	0.0305
C10	0.2841 (4)	−0.0149 (3)	−0.08814 (13)	0.0402
N11	1.2671 (3)	0.9068 (3)	0.20806 (11)	0.0549
C12	1.2555 (3)	0.7904 (3)	0.22713 (9)	0.0343
C13	1.2383 (3)	0.6400 (3)	0.25102 (8)	0.0303
C14	1.2224 (3)	0.6390 (2)	0.31816 (8)	0.0255
O15	1.07428 (19)	0.73225 (19)	0.33227 (6)	0.0322
C16	1.4029 (3)	0.6991 (2)	0.35002 (8)	0.0238
N17	1.4408 (2)	0.6523 (2)	0.41398 (7)	0.0245
C18	1.6277 (3)	0.7165 (3)	0.43570 (10)	0.0323
C19	1.2992 (3)	0.7148 (3)	0.45062 (8)	0.0279
C20	1.4500 (4)	0.4874 (3)	0.42137 (13)	0.0394
N21	0.9535 (3)	0.4159 (3)	0.45514 (11)	0.0531
C22	0.9660 (3)	0.2977 (3)	0.43772 (10)	0.0338
C23	0.9810 (3)	0.1461 (3)	0.41538 (9)	0.0306
C24	0.9950 (3)	0.1403 (2)	0.34836 (8)	0.0253
O25	1.14212 (19)	0.23254 (19)	0.33271 (6)	0.0326
C26	0.8145 (3)	0.1984 (2)	0.31640 (8)	0.0247
N27	0.7760 (2)	0.1497 (2)	0.25248 (7)	0.0245
C28	0.9175 (3)	0.2127 (3)	0.21587 (8)	0.0304
C29	0.5882 (3)	0.2126 (3)	0.23068 (10)	0.0326
C30	0.7678 (4)	−0.0158 (3)	0.24591 (13)	0.0417
Cl31	0.68275 (6)	0.08879 (8)	0.073991 (18)	0.0267
Cl32	0.74341 (6)	0.58876 (8)	0.259692 (19)	0.0267
Cl33	0.46947 (6)	0.09158 (9)	0.407349 (19)	0.0277
H293	0.5566	0.1906	0.1890	0.0481*
H292	0.5951	0.3196	0.2370	0.0484*
H291	0.4959	0.1695	0.2544	0.0492*
H281	0.8819	0.1926	0.1769	0.0451*
H283	1.0383	0.1666	0.2293	0.0450*
H282	0.9206	0.3147	0.2216	0.0451*
H302	0.7309	−0.0444	0.2060	0.0649*
H303	0.8890	−0.0600	0.2561	0.0647*
H301	0.6752	−0.0617	0.2693	0.0648*
H262	0.8159	0.3074	0.3193	0.0312*
H261	0.7105	0.1663	0.3372	0.0307*
H232	1.0923	0.0953	0.4311	0.0367*
H231	0.8639	0.0916	0.4204	0.0354*
H241	1.0101	0.0345	0.3369	0.0327*
H251	1.2353	0.1987	0.3511	0.0485*
H193	1.3319	0.6890	0.4898	0.0429*
H192	1.2947	0.8205	0.4465	0.0420*
H191	1.1789	0.6672	0.4354	0.0422*
H181	1.6529	0.6904	0.4755	0.0467*
H183	1.6263	0.8204	0.4318	0.0468*
H182	1.7204	0.6742	0.4135	0.0473*
H202	1.4901	0.4617	0.4609	0.0606*
H203	1.5372	0.4438	0.3963	0.0602*
H201	1.3317	0.4398	0.4123	0.0603*
H162	1.4006	0.8051	0.3463	0.0294*
H161	1.5100	0.6644	0.3309	0.0282*
H132	1.3439	0.5794	0.2418	0.0365*
H131	1.1140	0.5917	0.2392	0.0315*
H141	1.2051	0.5324	0.3288	0.0317*
H151	0.9725	0.7015	0.3139	0.0483*
H93	0.1222	0.1904	−0.1558	0.0451*
H92	0.1139	0.3161	−0.1120	0.0453*
H91	0.0002	0.1658	−0.1018	0.0441*
H81	0.4568	0.1851	−0.1445	0.0478*
H83	0.4507	0.3195	−0.1005	0.0483*
H82	0.5592	0.1745	−0.0800	0.0489*
H102	0.3088	−0.0433	−0.1273	0.0618*
H103	0.3918	−0.0555	−0.0634	0.0618*
H101	0.1701	−0.0634	−0.0775	0.0618*
H62	0.2846	0.3043	−0.0146	0.0306*
H61	0.4010	0.1728	0.0028	0.0289*
H32	0.2906	0.0744	0.0922	0.0365*
H31	0.0627	0.0930	0.0923	0.0311*
H41	0.0979	0.0323	0.0038	0.0318*
H51	−0.1290	0.1987	0.0180	0.0509*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0578 (15)	0.0637 (16)	0.0464 (13)	−0.0085 (12)	0.0065 (11)	−0.0177 (12)
C2	0.0269 (10)	0.0507 (14)	0.0255 (10)	−0.0002 (9)	0.0055 (8)	0.0002 (9)
C3	0.0281 (10)	0.0406 (11)	0.0205 (8)	0.0037 (8)	0.0044 (7)	0.0044 (8)
C4	0.0259 (9)	0.0288 (9)	0.0226 (8)	0.0016 (7)	0.0026 (7)	0.0014 (7)
O5	0.0223 (7)	0.0475 (9)	0.0325 (7)	0.0070 (6)	0.0043 (5)	0.0093 (7)
C6	0.0259 (9)	0.0298 (10)	0.0195 (8)	−0.0006 (7)	0.0010 (6)	0.0007 (7)
N7	0.0263 (8)	0.0263 (8)	0.0202 (7)	0.0017 (7)	0.0040 (6)	−0.0006 (6)
C8	0.0271 (10)	0.0351 (11)	0.0368 (11)	−0.0006 (9)	0.0104 (8)	−0.0008 (9)
C9	0.0300 (10)	0.0415 (12)	0.0195 (8)	−0.0005 (9)	0.0008 (7)	−0.0020 (8)
C10	0.0523 (16)	0.0245 (11)	0.0467 (14)	−0.0042 (10)	0.0191 (12)	−0.0066 (10)
N11	0.0514 (14)	0.0638 (16)	0.0486 (13)	−0.0051 (12)	0.0008 (10)	0.0177 (12)
C12	0.0268 (10)	0.0511 (14)	0.0244 (9)	−0.0003 (9)	0.0003 (8)	0.0016 (9)
C13	0.0271 (10)	0.0442 (11)	0.0192 (8)	0.0036 (8)	−0.0002 (7)	−0.0064 (8)
C14	0.0230 (9)	0.0288 (9)	0.0244 (8)	0.0012 (7)	0.0008 (6)	−0.0021 (7)
O15	0.0220 (7)	0.0446 (9)	0.0299 (7)	0.0063 (6)	0.0016 (5)	−0.0074 (7)
C16	0.0212 (8)	0.0275 (9)	0.0221 (8)	−0.0006 (7)	0.0001 (6)	−0.0016 (7)
N17	0.0214 (8)	0.0287 (8)	0.0225 (7)	0.0048 (7)	−0.0023 (6)	−0.0004 (6)
C18	0.0229 (9)	0.0354 (11)	0.0372 (11)	−0.0003 (8)	−0.0035 (8)	0.0014 (9)
C19	0.0278 (9)	0.0381 (11)	0.0183 (8)	0.0013 (8)	0.0055 (7)	−0.0012 (8)
C20	0.0461 (15)	0.0217 (10)	0.0483 (14)	0.0037 (9)	−0.0057 (11)	0.0011 (10)
N21	0.0530 (14)	0.0560 (15)	0.0518 (13)	−0.0055 (12)	0.0135 (11)	−0.0167 (12)
C22	0.0271 (10)	0.0469 (14)	0.0277 (10)	−0.0019 (9)	0.0045 (8)	−0.0005 (9)
C23	0.0289 (10)	0.0392 (11)	0.0234 (8)	−0.0036 (8)	0.0010 (7)	0.0056 (8)
C24	0.0242 (9)	0.0291 (9)	0.0224 (8)	0.0012 (7)	0.0015 (6)	0.0008 (7)
O25	0.0209 (7)	0.0479 (9)	0.0286 (7)	−0.0038 (6)	0.0006 (5)	0.0086 (7)
C26	0.0232 (9)	0.0296 (10)	0.0213 (8)	0.0020 (7)	0.0028 (6)	−0.0007 (7)
N27	0.0238 (8)	0.0279 (8)	0.0212 (7)	−0.0015 (7)	−0.0007 (6)	−0.0027 (7)
C28	0.0290 (10)	0.0415 (12)	0.0213 (8)	−0.0012 (9)	0.0048 (7)	−0.0025 (8)
C29	0.0234 (9)	0.0359 (12)	0.0377 (11)	0.0016 (8)	−0.0009 (8)	−0.0022 (9)
C30	0.0455 (15)	0.0235 (11)	0.0530 (15)	0.0020 (9)	−0.0106 (11)	−0.0051 (10)
Cl31	0.02254 (18)	0.0283 (2)	0.0287 (2)	−0.0005 (2)	0.00047 (14)	0.0018 (2)
Cl32	0.02404 (19)	0.0278 (2)	0.02883 (19)	−0.0006 (2)	0.00502 (14)	−0.0023 (2)
Cl33	0.02406 (18)	0.0287 (2)	0.03004 (19)	−0.0012 (2)	0.00127 (14)	0.0019 (2)

Geometric parameters (Å, º)

N1—C2	1.134 (3)	N17—C18	1.509 (3)
C2—C3	1.456 (3)	N17—C19	1.497 (3)
C3—C4	1.539 (3)	N17—C20	1.485 (3)
C3—H32	0.977	C18—H181	0.937
C3—H31	1.019	C18—H183	0.933
C4—O5	1.423 (2)	C18—H182	0.959
C4—C6	1.521 (3)	C19—H193	0.930
C4—H41	0.992	C19—H192	0.950
O5—H51	0.884	C19—H191	1.001
C6—N7	1.518 (2)	C20—H202	0.947
C6—H62	0.963	C20—H203	0.976
C6—H61	0.943	C20—H201	0.962
N7—C8	1.506 (3)	N21—C22	1.136 (3)
N7—C9	1.499 (3)	C22—C23	1.456 (4)
N7—C10	1.481 (3)	C23—C24	1.542 (3)
C8—H81	0.966	C23—H232	0.964
C8—H83	0.956	C23—H231	0.996
C8—H82	0.962	C24—O25	1.423 (2)
C9—H93	0.914	C24—C26	1.524 (3)
C9—H92	0.931	C24—H241	0.990
C9—H91	1.020	O25—H251	0.817
C10—H102	0.962	C26—N27	1.519 (2)
C10—H103	0.986	C26—H262	0.977
C10—H101	0.986	C26—H261	0.975
N11—C12	1.134 (3)	N27—C28	1.498 (3)
C12—C13	1.461 (3)	N27—C29	1.511 (3)
C13—C14	1.546 (3)	N27—C30	1.488 (3)
C13—H132	0.979	C28—H281	0.917
C13—H131	1.012	C28—H283	0.989
C14—O15	1.423 (2)	C28—H282	0.921
C14—C16	1.530 (3)	C29—H293	0.975
C14—H141	0.994	C29—H292	0.968
O15—H151	0.856	C29—H291	0.982
C16—N17	1.515 (2)	C30—H302	0.957
C16—H162	0.952	C30—H303	0.971
C16—H161	0.980	C30—H301	0.989
N1—C2—C3	179.5 (2)	C18—N17—C19	108.69 (17)
C2—C3—C4	113.03 (18)	C16—N17—C20	112.63 (18)
C2—C3—H32	111.6	C18—N17—C20	108.16 (19)
C4—C3—H32	111.0	C19—N17—C20	109.4 (2)
C2—C3—H31	113.5	N17—C18—H181	107.7
C4—C3—H31	93.7	N17—C18—H183	110.3
H32—C3—H31	112.8	H181—C18—H183	109.9
C3—C4—O5	111.10 (16)	N17—C18—H182	109.4
C3—C4—C6	109.16 (16)	H181—C18—H182	109.5
O5—C4—C6	108.40 (16)	H183—C18—H182	110.0
C3—C4—H41	107.4	N17—C19—H193	108.7
O5—C4—H41	110.7	N17—C19—H192	109.6
C6—C4—H41	110.1	H193—C19—H192	110.1
C4—O5—H51	111.6	N17—C19—H191	105.8
C4—C6—N7	115.48 (16)	H193—C19—H191	110.9
C4—C6—H62	108.7	H192—C19—H191	111.7
N7—C6—H62	109.1	N17—C20—H202	110.8
C4—C6—H61	112.4	N17—C20—H203	110.8
N7—C6—H61	108.6	H202—C20—H203	107.8
H62—C6—H61	101.6	N17—C20—H201	112.7
C6—N7—C8	107.20 (16)	H202—C20—H201	106.2
C6—N7—C9	110.76 (15)	H203—C20—H201	108.4
C8—N7—C9	108.65 (16)	N21—C22—C23	179.7 (3)
C6—N7—C10	112.44 (17)	C22—C23—C24	113.12 (18)
C8—N7—C10	108.18 (19)	C22—C23—H232	113.5
C9—N7—C10	109.5 (2)	C24—C23—H232	102.4
N7—C8—H81	110.1	C22—C23—H231	108.7
N7—C8—H83	109.2	C24—C23—H231	103.9
H81—C8—H83	109.4	H232—C23—H231	114.9
N7—C8—H82	108.6	C23—C24—O25	110.82 (16)
H81—C8—H82	110.3	C23—C24—C26	108.79 (17)
H83—C8—H82	109.2	O25—C24—C26	108.26 (16)
N7—C9—H93	108.8	C23—C24—H241	108.3
N7—C9—H92	108.7	O25—C24—H241	112.4
H93—C9—H92	109.6	C26—C24—H241	108.2
N7—C9—H91	107.4	C24—O25—H251	105.1
H93—C9—H91	111.6	C24—C26—N27	115.26 (16)
H92—C9—H91	110.7	C24—C26—H262	107.8
N7—C10—H102	111.7	N27—C26—H262	110.5
N7—C10—H103	108.8	C24—C26—H261	109.8
H102—C10—H103	102.9	N27—C26—H261	107.8
N7—C10—H101	112.8	H262—C26—H261	105.3
H102—C10—H101	110.7	C26—N27—C28	110.88 (15)
H103—C10—H101	109.5	C26—N27—C29	106.33 (16)
N11—C12—C13	179.2 (2)	C28—N27—C29	108.88 (16)
C12—C13—C14	113.09 (18)	C26—N27—C30	112.52 (18)
C12—C13—H132	109.4	C28—N27—C30	109.9 (2)
C14—C13—H132	110.4	C29—N27—C30	108.16 (19)
C12—C13—H131	113.6	N27—C28—H281	108.9
C14—C13—H131	96.1	N27—C28—H283	107.9
H132—C13—H131	113.8	H281—C28—H283	111.8
C13—C14—O15	110.75 (16)	N27—C28—H282	107.5
C13—C14—C16	108.73 (17)	H281—C28—H282	109.5
O15—C14—C16	108.50 (16)	H283—C28—H282	111.2
C13—C14—H141	105.8	N27—C29—H293	111.1
O15—C14—H141	112.9	N27—C29—H292	106.7
C16—C14—H141	110.1	H293—C29—H292	110.4
C14—O15—H151	109.6	N27—C29—H291	108.4
C14—C16—N17	115.06 (16)	H293—C29—H291	110.6
C14—C16—H162	107.5	H292—C29—H291	109.5
N17—C16—H162	111.1	N27—C30—H302	111.5
C14—C16—H161	111.0	N27—C30—H303	110.8
N17—C16—H161	105.4	H302—C30—H303	106.1
H162—C16—H161	106.5	N27—C30—H301	112.4
C16—N17—C18	106.30 (17)	H302—C30—H301	105.1
C16—N17—C19	111.46 (15)	H303—C30—H301	110.6

(RScarnitinenitrileiodide)

Crystal data

C7H15N2O·I	F(000) = 2112
Mr = 270.11	Dx = 1.652 Mg m^−3
Orthorhombic, Pbca	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 9526 reflections
a = 13.4725 (2) Å	θ = 5–79°
b = 9.8551 (1) Å	µ = 22.83 mm^−1
c = 32.7259 (4) Å	T = 160 K
V = 4345.11 (9) Å^3	Plate, colorless
Z = 16	0.12 × 0.10 × 0.05 mm

Data collection

Oxford Diffraction SuperNova diffractometer	4082 reflections with I > 2.0σ(I)
Focussing mirrors monochromator	Rint = 0.032
ω scans	θmax = 74.5°, θmin = 4.3°
Absorption correction: multi-scan CrysAlisPro (Rigaku Oxford Diffraction, 2017)	h = −16→14
Tmin = 0.12, Tmax = 0.34	k = −11→12
17435 measured reflections	l = −39→40
4437 independent reflections

Refinement

Refinement on F^2	Primary atom site location: other
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.049	H-atom parameters constrained
wR(F^2) = 0.113	Method = Modified Sheldrick w = 1/[σ^2(F^2) + ( 0.03P)^2 + 31.74P] , where P = (max(Fo^2,0) + 2Fc^2)/3
S = 1.01	(Δ/σ)max = 0.002
4437 reflections	Δρmax = 1.97 e Å^−3
209 parameters	Δρmin = −1.61 e Å^−3
2 restraints

Special details

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1K.

Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	0.7558 (6)	0.4679 (8)	0.54891 (18)	0.0775
C2	0.7749 (5)	0.3800 (8)	0.56924 (18)	0.0528
C3	0.7980 (5)	0.2617 (7)	0.59428 (19)	0.0499
C4	0.8279 (4)	0.3040 (6)	0.63764 (17)	0.0403
O5	0.7493 (3)	0.3766 (4)	0.65652 (12)	0.0477
C6	0.8555 (4)	0.1739 (6)	0.65983 (17)	0.0417
N7	0.9104 (4)	0.1897 (5)	0.70008 (13)	0.0369
C8	0.8546 (5)	0.2769 (6)	0.73039 (18)	0.0457
C9	1.0121 (4)	0.2486 (7)	0.69398 (18)	0.0457
C10	0.9205 (5)	0.0500 (7)	0.7174 (2)	0.0527
N11	0.2629 (5)	0.5423 (7)	0.70320 (18)	0.0660
C12	0.2715 (5)	0.4543 (8)	0.68075 (17)	0.0485
C13	0.2856 (5)	0.3405 (7)	0.65267 (18)	0.0501
C14	0.3472 (4)	0.3832 (6)	0.61548 (17)	0.0478
C16	0.3621 (5)	0.2517 (6)	0.59102 (16)	0.0396
N17	0.4157 (3)	0.2668 (4)	0.55040 (13)	0.0343
C18	0.3600 (5)	0.3542 (7)	0.52138 (17)	0.0484
C19	0.5179 (5)	0.3217 (8)	0.5561 (2)	0.0543
C20	0.4229 (6)	0.1255 (6)	0.5330 (2)	0.0554
I21	0.07520 (3)	0.24189 (4)	0.567724 (13)	0.0539
I22	0.55599 (3)	0.15399 (4)	0.677831 (12)	0.0495
H31	0.8520	0.2128	0.5817	0.0599*
H32	0.7403	0.2038	0.5957	0.0599*
H41	0.8866	0.3641	0.6360	0.0480*
H61	0.7953	0.1226	0.6650	0.0497*
H62	0.8993	0.1222	0.6425	0.0499*
H82	0.8890	0.2746	0.7561	0.0677*
H81	0.7882	0.2414	0.7332	0.0680*
H83	0.8521	0.3682	0.7204	0.0680*
H92	1.0480	0.2473	0.7192	0.0677*
H93	1.0476	0.1988	0.6737	0.0679*
H91	1.0065	0.3399	0.6848	0.0681*
H102	0.9553	0.0556	0.7429	0.0789*
H101	0.8556	0.0121	0.7220	0.0792*
H103	0.9572	−0.0065	0.6989	0.0788*
H132	0.3215	0.2697	0.6668	0.0602*
H131	0.2217	0.3065	0.6442	0.0600*
H161	0.4015	0.1909	0.6076	0.0479*
H162	0.2981	0.2106	0.5852	0.0480*
H182	0.3903	0.3494	0.4948	0.0727*
H183	0.3611	0.4471	0.5310	0.0729*
H181	0.2918	0.3227	0.5194	0.0728*
H191	0.5530	0.3146	0.5308	0.0819*
H193	0.5510	0.2681	0.5766	0.0818*
H192	0.5141	0.4154	0.5649	0.0818*
H51	0.7061	0.3177	0.6592	0.0721*
H203	0.4584	0.1286	0.5077	0.0839*
H202	0.4581	0.0693	0.5523	0.0840*
H201	0.3573	0.0909	0.5287	0.0839*
O151	0.4397 (5)	0.4364 (10)	0.6315 (3)	0.0800	0.647 (11)
O152	0.2671 (9)	0.4530 (15)	0.5946 (4)	0.0782	0.353 (11)
H141	0.3140	0.4534	0.5993	0.0582*	0.647 (11)
H142	0.4063	0.4390	0.6206	0.0581*	0.353 (11)
H1511	0.4663	0.3705	0.6422	0.0918*	0.647 (11)
H1521	0.2221	0.4010	0.5883	0.0812*	0.353 (11)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.107 (6)	0.079 (5)	0.046 (3)	0.032 (4)	−0.006 (4)	−0.002 (3)
C2	0.059 (4)	0.064 (4)	0.035 (3)	0.014 (3)	−0.009 (3)	−0.006 (3)
C3	0.056 (4)	0.051 (4)	0.043 (3)	0.008 (3)	−0.011 (3)	−0.007 (3)
C4	0.043 (3)	0.040 (3)	0.037 (3)	0.004 (3)	−0.001 (2)	−0.003 (2)
O5	0.048 (2)	0.044 (2)	0.051 (2)	0.0083 (19)	0.004 (2)	−0.0053 (19)
C6	0.044 (3)	0.043 (3)	0.038 (3)	0.002 (3)	0.001 (2)	−0.003 (2)
N7	0.042 (2)	0.040 (3)	0.028 (2)	0.004 (2)	0.0054 (19)	−0.0022 (19)
C8	0.054 (3)	0.046 (3)	0.037 (3)	0.012 (3)	0.010 (3)	−0.005 (3)
C9	0.039 (3)	0.054 (4)	0.044 (3)	−0.005 (3)	0.002 (2)	0.003 (3)
C10	0.071 (4)	0.042 (3)	0.045 (3)	0.006 (3)	−0.004 (3)	0.003 (3)
N11	0.085 (4)	0.067 (4)	0.047 (3)	0.019 (4)	0.016 (3)	0.001 (3)
C12	0.046 (3)	0.068 (4)	0.032 (3)	0.006 (3)	0.009 (2)	0.004 (3)
C13	0.052 (3)	0.063 (4)	0.035 (3)	−0.013 (3)	0.005 (3)	−0.001 (3)
C14	0.070 (4)	0.039 (3)	0.034 (3)	0.007 (3)	0.011 (3)	0.004 (2)
C16	0.052 (3)	0.034 (3)	0.032 (3)	−0.002 (3)	0.002 (2)	0.007 (2)
N17	0.045 (2)	0.028 (2)	0.031 (2)	−0.0002 (19)	−0.0007 (19)	−0.0010 (18)
C18	0.060 (4)	0.052 (4)	0.032 (3)	0.003 (3)	−0.001 (3)	0.009 (3)
C19	0.050 (4)	0.066 (4)	0.047 (4)	−0.008 (3)	−0.002 (3)	0.007 (3)
C20	0.079 (5)	0.036 (3)	0.051 (4)	0.001 (3)	0.011 (3)	−0.010 (3)
I21	0.0656 (3)	0.0482 (2)	0.0478 (2)	0.0117 (2)	−0.01535 (19)	0.00067 (18)
I22	0.0469 (2)	0.0507 (2)	0.0510 (2)	0.00453 (18)	0.00861 (17)	0.00087 (18)
O151	0.061 (5)	0.092 (7)	0.087 (6)	−0.041 (5)	0.021 (4)	−0.055 (5)
O152	0.135 (15)	0.054 (9)	0.045 (7)	0.038 (10)	0.007 (8)	0.008 (6)

Geometric parameters (Å, º)

N1—C2	1.123 (9)	C13—C14	1.532 (8)
C2—C3	1.459 (9)	C13—H132	0.967
C3—C4	1.532 (8)	C13—H131	0.965
C3—H31	0.964	C14—C16	1.537 (8)
C3—H32	0.965	C14—O151	1.4508 (10)
C4—O5	1.420 (7)	C14—H141	0.979
C4—C6	1.519 (8)	C14—C16	1.537 (8)
C4—H41	0.989	C14—O152	1.4506 (10)
O5—H51	0.827	C14—H142	0.982
C6—N7	1.518 (7)	C16—N17	1.520 (7)
C6—H61	0.972	C16—H161	0.967
C6—H62	0.965	C16—H162	0.971
N7—C8	1.511 (7)	N17—C18	1.486 (7)
N7—C9	1.502 (7)	N17—C19	1.491 (8)
N7—C10	1.496 (8)	N17—C20	1.508 (7)
C8—H82	0.961	C18—H182	0.961
C8—H81	0.966	C18—H183	0.968
C8—H83	0.958	C18—H181	0.971
C9—H92	0.956	C19—H191	0.958
C9—H93	0.954	C19—H193	0.963
C9—H91	0.952	C19—H192	0.968
C10—H102	0.959	C20—H203	0.958
C10—H101	0.962	C20—H202	0.964
C10—H103	0.960	C20—H201	0.959
N11—C12	1.143 (9)	O151—H1511	0.820
C12—C13	1.462 (9)	O152—H1521	0.820
N1—C2—C3	177.5 (7)	C12—C13—H131	109.3
C2—C3—C4	111.0 (5)	C14—C13—H131	110.4
C2—C3—H31	108.6	H132—C13—H131	109.5
C4—C3—H31	109.5	C13—C14—C16	104.7 (5)
C2—C3—H32	109.1	C13—C14—O151	106.1 (5)
C4—C3—H32	109.2	C16—C14—O151	112.3 (5)
H31—C3—H32	109.4	C13—C14—H141	112.2
C3—C4—O5	110.1 (5)	C16—C14—H141	112.0
C3—C4—C6	106.1 (5)	O151—C14—H141	109.4
O5—C4—C6	113.6 (5)	C13—C14—C16	104.7 (5)
C3—C4—H41	108.8	C13—C14—O152	95.9 (7)
O5—C4—H41	108.5	C16—C14—O152	104.6 (7)
C6—C4—H41	109.6	C13—C14—H142	117.3
C4—O5—H51	102.5	C16—C14—H142	117.0
C4—C6—N7	116.6 (5)	O152—C14—H142	114.6
C4—C6—H61	108.5	C14—C16—N17	115.8 (4)
N7—C6—H61	107.9	C14—C16—H161	107.5
C4—C6—H62	108.3	N17—C16—H161	107.0
N7—C6—H62	105.6	C14—C16—H162	109.6
H61—C6—H62	109.8	N17—C16—H162	107.0
C6—N7—C8	112.7 (5)	H161—C16—H162	109.8
C6—N7—C9	111.6 (4)	C16—N17—C18	112.1 (4)
C8—N7—C9	108.7 (5)	C16—N17—C19	111.3 (4)
C6—N7—C10	106.2 (5)	C18—N17—C19	109.7 (5)
C8—N7—C10	108.6 (4)	C16—N17—C20	105.6 (4)
C9—N7—C10	108.8 (5)	C18—N17—C20	109.1 (5)
N7—C8—H82	108.8	C19—N17—C20	108.9 (5)
N7—C8—H81	108.6	N17—C18—H182	109.5
H82—C8—H81	110.7	N17—C18—H183	109.4
N7—C8—H83	109.1	H182—C18—H183	109.5
H82—C8—H83	109.8	N17—C18—H181	109.5
H81—C8—H83	109.8	H182—C18—H181	109.0
N7—C9—H92	110.0	H183—C18—H181	109.8
N7—C9—H93	110.6	N17—C19—H191	108.7
H92—C9—H93	109.8	N17—C19—H193	108.4
N7—C9—H91	109.6	H191—C19—H193	109.5
H92—C9—H91	108.9	N17—C19—H192	109.6
H93—C9—H91	107.9	H191—C19—H192	110.7
N7—C10—H102	108.7	H193—C19—H192	110.0
N7—C10—H101	109.4	N17—C20—H203	109.2
H102—C10—H101	109.4	N17—C20—H202	108.4
N7—C10—H103	109.9	H203—C20—H202	109.9
H102—C10—H103	109.4	N17—C20—H201	109.0
H101—C10—H103	110.0	H203—C20—H201	110.0
N11—C12—C13	178.0 (7)	H202—C20—H201	110.3
C12—C13—C14	111.1 (5)	C14—O151—H1511	104.1
C12—C13—H132	108.5	C14—O152—H1521	111.7
C14—C13—H132	107.9

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H61···O5^i	0.97	2.51	3.254 (9)	133

Symmetry code: (i) −x+3/2, y−1/2, z.

(Rcarnitinenitrilechloride)

Crystal data

C7H15N2O·Cl	F(000) = 191.998
Mr = 178.66	Dx = 1.212 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 10124 reflections
a = 7.2902 (2) Å	θ = 3–34°
b = 8.9099 (3) Å	µ = 0.34 mm^−1
c = 7.8789 (3) Å	T = 160 K
β = 107.024 (3)°	Plate, colorless
V = 489.35 (3) Å^3	0.30 × 0.20 × 0.07 mm
Z = 2

Data collection

Oxford Diffraction SuperNova diffractometer	3428 reflections with I > 2.0σ(I)
Graphite monochromator	Rint = 0.039
ω scans	θmax = 33.1°, θmin = 2.7°
Absorption correction: multi-scan CrysAlisPro, (Agilent, 2011)	h = −11→11
Tmin = 0.59, Tmax = 0.98	k = −13→13
15361 measured reflections	l = −12→11
3726 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: difference Fourier map
Least-squares matrix: full	H-atom parameters not refined
R[F^2 > 2σ(F^2)] = 0.032	Method = Modified Sheldrick w = 1/[σ^2(F^2) + ( 0.06P)^2 + 0.02P] , where P = (max(Fo^2,0) + 2Fc^2)/3
wR(F^2) = 0.081	(Δ/σ)max = 0.003
S = 0.95	Δρmax = 0.39 e Å^−3
3726 reflections	Δρmin = −0.29 e Å^−3
101 parameters	Absolute structure: Flack (1983), 1757 Friedel-pairs
1 restraint	Absolute structure parameter: −0.01 (4)
Primary atom site location: structure-invariant direct methods

Special details

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1K.

Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.4227 (2)	0.29988 (19)	0.86539 (19)	0.0439
C2	0.42518 (18)	0.4188 (2)	0.81389 (17)	0.0298
C3	0.42895 (18)	0.57227 (19)	0.74730 (15)	0.0264
C4	0.39881 (15)	0.57640 (17)	0.54599 (14)	0.0216
O5	0.53528 (11)	0.48579 (16)	0.49785 (11)	0.0269
C6	0.19831 (15)	0.51844 (17)	0.45120 (14)	0.0204
N7	0.11690 (14)	0.56477 (17)	0.25902 (13)	0.0210
C8	0.1055 (2)	0.73162 (19)	0.2394 (2)	0.0339
C9	−0.08373 (15)	0.50281 (19)	0.19391 (17)	0.0278
C10	0.23296 (17)	0.50150 (19)	0.14668 (15)	0.0262
Cl11	−0.09007 (3)	0.62594 (13)	0.72235 (3)	0.0245
H41	0.4069	0.6826	0.5146	0.0286*
H61	0.2012	0.4142	0.4560	0.0265*
H62	0.1084	0.5534	0.5132	0.0239*
H93	−0.1391	0.5301	0.0690	0.0411*
H91	−0.0787	0.3985	0.2056	0.0429*
H92	−0.1576	0.5456	0.2667	0.0421*
H82	0.0367	0.7548	0.1145	0.0544*
H83	0.0350	0.7684	0.3209	0.0555*
H81	0.2340	0.7716	0.2709	0.0551*
H101	0.1672	0.5260	0.0228	0.0388*
H103	0.2411	0.3969	0.1621	0.0421*
H102	0.3616	0.5437	0.1864	0.0402*
H32	0.3304	0.6272	0.7801	0.0334*
H31	0.5602	0.6057	0.8065	0.0319*
H51	0.6362	0.5188	0.5584	0.0422*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0468 (7)	0.0446 (7)	0.0429 (7)	0.0060 (6)	0.0173 (6)	0.0121 (6)
C2	0.0267 (5)	0.0396 (7)	0.0232 (5)	0.0039 (5)	0.0073 (4)	0.0027 (5)
C3	0.0271 (5)	0.0281 (5)	0.0231 (4)	−0.0001 (4)	0.0060 (4)	−0.0046 (4)
C4	0.0209 (4)	0.0206 (4)	0.0224 (4)	−0.0012 (4)	0.0050 (3)	−0.0019 (4)
O5	0.0197 (3)	0.0333 (4)	0.0270 (4)	0.0001 (3)	0.0058 (3)	−0.0073 (3)
C6	0.0204 (4)	0.0197 (4)	0.0211 (4)	−0.0009 (4)	0.0059 (3)	−0.0004 (3)
N7	0.0200 (4)	0.0179 (4)	0.0234 (4)	0.0009 (3)	0.0037 (3)	0.0019 (3)
C8	0.0352 (7)	0.0171 (5)	0.0429 (7)	0.0010 (5)	0.0013 (5)	0.0038 (5)
C9	0.0191 (5)	0.0253 (6)	0.0347 (6)	−0.0004 (4)	0.0012 (4)	−0.0003 (4)
C10	0.0265 (5)	0.0305 (6)	0.0216 (5)	0.0010 (4)	0.0071 (4)	0.0012 (4)
Cl11	0.02216 (10)	0.02147 (11)	0.02860 (11)	0.00025 (10)	0.00535 (8)	−0.00162 (10)

Geometric parameters (Å, º)

N1—C2	1.1370 (19)	N7—C8	1.4944 (18)
C2—C3	1.467 (2)	N7—C9	1.5060 (15)
C3—C4	1.5366 (16)	N7—C10	1.5019 (17)
C3—H32	0.965	C8—H82	0.987
C3—H31	0.980	C8—H83	0.988
C4—O5	1.4165 (14)	C8—H81	0.964
C4—C6	1.5237 (15)	C9—H93	0.979
C4—H41	0.984	C9—H91	0.934
O5—H51	0.806	C9—H92	0.972
C6—N7	1.5130 (14)	C10—H101	0.978
C6—H61	0.929	C10—H103	0.940
C6—H62	0.976	C10—H102	0.973
N1—C2—C3	179.82 (14)	C8—N7—C9	108.08 (10)
C2—C3—C4	112.30 (10)	C6—N7—C10	111.33 (9)
C2—C3—H32	106.4	C8—N7—C10	109.66 (12)
C4—C3—H32	111.8	C9—N7—C10	108.67 (9)
C2—C3—H31	103.4	N7—C8—H82	107.9
C4—C3—H31	108.0	N7—C8—H83	106.6
H32—C3—H31	114.7	H82—C8—H83	111.7
C3—C4—O5	111.31 (9)	N7—C8—H81	108.7
C3—C4—C6	108.94 (10)	H82—C8—H81	110.6
O5—C4—C6	108.89 (9)	H83—C8—H81	111.2
C3—C4—H41	106.3	N7—C9—H93	109.0
O5—C4—H41	112.5	N7—C9—H91	109.0
C6—C4—H41	108.8	H93—C9—H91	109.8
C4—O5—H51	102.9	N7—C9—H92	107.8
C4—C6—N7	115.92 (9)	H93—C9—H92	111.1
C4—C6—H61	108.2	H91—C9—H92	110.2
N7—C6—H61	108.1	N7—C10—H101	108.0
C4—C6—H62	109.6	N7—C10—H103	108.8
N7—C6—H62	106.8	H101—C10—H103	110.2
H61—C6—H62	108.0	N7—C10—H102	108.7
C6—N7—C8	111.62 (10)	H101—C10—H102	112.3
C6—N7—C9	107.35 (9)	H103—C10—H102	108.9

(Rcarnitinenitrilebromide)

Crystal data

C7H15N2O·Br	F(000) = 228
Mr = 223.11	Dx = 1.427 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 9220 reflections
a = 7.5269 (2) Å	θ = 3–30°
b = 9.1017 (3) Å	µ = 3.92 mm^−1
c = 7.9300 (3) Å	T = 160 K
β = 107.161 (4)°	Plate, colorless
V = 519.08 (3) Å^3	0.12 × 0.10 × 0.03 mm
Z = 2

Data collection

Oxford Diffraction SuperNova diffractometer	3118 reflections with I > 2.0σ(I)
Graphite monochromator	Rint = 0.034
ω scans	θmax = 31.5°, θmin = 2.7°
Absorption correction: multi-scan CrysAlisPro, (Agilent, 2011)	h = −10→11
Tmin = 0.64, Tmax = 0.90	k = −13→13
16508 measured reflections	l = −11→11
3402 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: difference Fourier map
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.029	Method = Modified Sheldrick w = 1/[σ^2(F^2) + ( 0.04P)^2 + 0.27P] , where P = (max(Fo^2,0) + 2Fc^2)/3
wR(F^2) = 0.072	(Δ/σ)max = 0.001
S = 0.97	Δρmax = 0.47 e Å^−3
3402 reflections	Δρmin = −0.53 e Å^−3
101 parameters	Absolute structure: Flack (1983), 1581 Friedel-pairs
1 restraint	Absolute structure parameter: 0.043 (10)
Primary atom site location: structure-invariant direct methods

Special details

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1K.

Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.9125 (4)	0.2003 (3)	1.3586 (4)	0.0451
C2	0.9201 (4)	0.3168 (3)	1.3109 (3)	0.0296
C3	0.9332 (4)	0.4668 (3)	1.2495 (3)	0.0262
C4	0.9026 (3)	0.4744 (3)	1.0483 (3)	0.0202
O5	1.0304 (2)	0.3826 (2)	0.9981 (2)	0.0255
C6	0.7066 (3)	0.4236 (3)	0.9531 (3)	0.0193
N7	0.6291 (3)	0.4722 (3)	0.7627 (3)	0.0192
C8	0.6234 (5)	0.6354 (3)	0.7463 (5)	0.0339
C9	0.4325 (3)	0.4158 (3)	0.6981 (3)	0.0270
C10	0.7395 (3)	0.4081 (3)	0.6498 (3)	0.0255
Br11	0.41054 (3)	0.53206 (11)	1.21779 (3)	0.0266
H103	0.6766	0.4333	0.5370	0.0387*
H102	0.8563	0.4509	0.6782	0.0382*
H101	0.7481	0.3060	0.6655	0.0373*
H83	0.5601	0.6727	0.8257	0.0512*
H82	0.7459	0.6682	0.7737	0.0506*
H81	0.5524	0.6600	0.6280	0.0496*
H93	0.3631	0.4540	0.7700	0.0388*
H92	0.4381	0.3096	0.7057	0.0385*
H91	0.3805	0.4450	0.5821	0.0407*
H32	1.0522	0.5041	1.3078	0.0319*
H31	0.8461	0.5271	1.2816	0.0331*
H41	0.9192	0.5751	1.0231	0.0230*
H62	0.6260	0.4620	1.0122	0.0230*
H61	0.7016	0.3199	0.9544	0.0218*
H51	1.1098	0.4279	1.0403	0.0381*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0471 (16)	0.0515 (16)	0.0373 (14)	0.0049 (13)	0.0136 (12)	0.0120 (12)
C2	0.0242 (11)	0.0437 (16)	0.0213 (11)	0.0044 (10)	0.0075 (9)	0.0024 (10)
C3	0.0256 (12)	0.0331 (12)	0.0192 (10)	0.0006 (9)	0.0052 (9)	−0.0051 (9)
C4	0.0202 (10)	0.0214 (9)	0.0189 (9)	−0.0009 (8)	0.0059 (8)	−0.0029 (8)
O5	0.0176 (8)	0.0341 (9)	0.0244 (8)	0.0010 (7)	0.0054 (6)	−0.0071 (7)
C6	0.0181 (9)	0.0230 (10)	0.0167 (9)	0.0004 (8)	0.0051 (8)	−0.0002 (8)
N7	0.0185 (9)	0.0167 (10)	0.0214 (9)	0.0021 (8)	0.0045 (7)	0.0008 (8)
C8	0.0377 (16)	0.0136 (13)	0.0454 (16)	0.0017 (11)	0.0047 (13)	0.0051 (12)
C9	0.0176 (10)	0.0302 (13)	0.0297 (12)	−0.0007 (9)	0.0015 (9)	−0.0001 (10)
C10	0.0237 (11)	0.0365 (13)	0.0183 (10)	0.0029 (10)	0.0091 (8)	0.0018 (9)
Br11	0.02418 (10)	0.02568 (10)	0.02912 (10)	0.00152 (14)	0.00641 (7)	−0.00089 (14)

Geometric parameters (Å, º)

N1—C2	1.133 (4)	N7—C8	1.491 (4)
C2—C3	1.463 (4)	N7—C9	1.506 (3)
C3—C4	1.545 (3)	N7—C10	1.507 (3)
C3—H32	0.942	C8—H83	0.957
C3—H31	0.946	C8—H82	0.932
C4—O5	1.417 (3)	C8—H81	0.959
C4—C6	1.518 (3)	C9—H93	0.946
C4—H41	0.954	C9—H92	0.968
O5—H51	0.722	C9—H91	0.926
C6—N7	1.515 (3)	C10—H103	0.909
C6—H62	0.937	C10—H102	0.926
C6—H61	0.944	C10—H101	0.938
N1—C2—C3	179.0 (3)	C8—N7—C9	108.0 (3)
C2—C3—C4	112.4 (2)	C6—N7—C10	111.21 (19)
C2—C3—H32	108.7	C8—N7—C10	109.9 (3)
C4—C3—H32	108.7	C9—N7—C10	108.9 (2)
C2—C3—H31	109.4	N7—C8—H83	107.7
C4—C3—H31	110.4	N7—C8—H82	107.3
H32—C3—H31	107.0	H83—C8—H82	112.6
C3—C4—O5	110.93 (19)	N7—C8—H81	108.1
C3—C4—C6	109.06 (19)	H83—C8—H81	108.6
O5—C4—C6	108.75 (19)	H82—C8—H81	112.3
C3—C4—H41	105.7	N7—C9—H93	109.4
O5—C4—H41	111.5	N7—C9—H92	107.4
C6—C4—H41	110.9	H93—C9—H92	110.6
C4—O5—H51	94.0	N7—C9—H91	109.0
C4—C6—N7	115.99 (19)	H93—C9—H91	110.2
C4—C6—H62	108.4	H92—C9—H91	110.3
N7—C6—H62	105.9	N7—C10—H103	105.6
C4—C6—H61	109.6	N7—C10—H102	110.0
N7—C6—H61	107.3	H103—C10—H102	108.4
H62—C6—H61	109.5	N7—C10—H101	109.4
C6—N7—C8	111.7 (2)	H103—C10—H101	112.1
C6—N7—C9	106.8 (2)	H102—C10—H101	111.2

(Rcarnitinenitrileiodide)

Crystal data

CC7H15N2O·I	F(000) = 528
Mr = 270.11	Dx = 1.675 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 14266 reflections
a = 7.5850 (1) Å	θ = 2–33°
b = 10.8242 (2) Å	µ = 2.95 mm^−1
c = 13.0468 (3) Å	T = 160 K
V = 1071.16 (3) Å^3	Prism, colorless
Z = 4	0.25 × 0.12 × 0.10 mm

Data collection

Oxford Diffraction SuperNova diffractometer	3544 reflections with I > 2.0σ(I)
Graphite monochromator	Rint = 0.021
ω scans	θmax = 32.9°, θmin = 2.4°
Absorption correction: multi-scan CrysAlisPro, (Agilent, 2011)	h = −11→9
Tmin = 0.47, Tmax = 0.75	k = −15→16
17375 measured reflections	l = −19→19
3606 independent reflections

Refinement

Refinement on F^2	H-atom parameters constrained
Least-squares matrix: full	Method = Modified Sheldrick w = 1/[σ^2(F^2) + ( 0.01P)^2 + 0.25P] , where P = (max(Fo^2,0) + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.013	(Δ/σ)max = 0.002
wR(F^2) = 0.030	Δρmax = 0.39 e Å^−3
S = 0.99	Δρmin = −0.41 e Å^−3
3606 reflections	Extinction correction: Larson (1970), Equation 22
101 parameters	Extinction coefficient: 31.271
0 restraints	Absolute structure: Flack (1983), 1481 Friedel-pairs
Primary atom site location: Other	Absolute structure parameter: −0.018 (12)
Hydrogen site location: difference Fourier map

Special details

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1K.

Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	−0.09118 (19)	0.85547 (11)	0.76082 (10)	0.0321
C2	−0.03026 (17)	0.76975 (13)	0.72543 (11)	0.0231
C3	0.04857 (17)	0.65622 (13)	0.68432 (12)	0.0256
C4	0.24273 (15)	0.64097 (11)	0.71711 (9)	0.0177
O5	0.34704 (13)	0.73213 (9)	0.66875 (8)	0.0245
C6	0.25703 (16)	0.65378 (11)	0.83324 (10)	0.0182
N7	0.42553 (14)	0.60624 (9)	0.88085 (8)	0.0172
C8	0.58628 (19)	0.67126 (13)	0.84080 (10)	0.0250
C9	0.4143 (2)	0.63029 (12)	0.99430 (9)	0.0243
C10	0.44722 (19)	0.46984 (12)	0.86448 (12)	0.0296
I11	0.591822 (11)	0.514611 (8)	0.538035 (7)	0.0274
H41	0.2808	0.5608	0.6970	0.0205*
H61	0.2542	0.7404	0.8497	0.0208*
H62	0.1619	0.6123	0.8660	0.0208*
H91	0.5174	0.5966	1.0255	0.0358*
H92	0.4064	0.7183	1.0036	0.0359*
H93	0.3086	0.5918	1.0192	0.0363*
H101	0.5534	0.4450	0.9010	0.0438*
H103	0.4634	0.4529	0.7911	0.0438*
H102	0.3458	0.4280	0.8921	0.0449*
H83	0.6895	0.6415	0.8779	0.0385*
H82	0.5973	0.6486	0.7698	0.0380*
H81	0.5707	0.7585	0.8497	0.0399*
H32	0.0436	0.6590	0.6116	0.0329*
H31	−0.0220	0.5883	0.7047	0.0328*
H51	0.4046	0.6968	0.6261	0.0374*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0290 (6)	0.0308 (6)	0.0366 (6)	0.0099 (6)	−0.0039 (6)	−0.0007 (5)
C2	0.0185 (6)	0.0252 (6)	0.0257 (6)	0.0028 (5)	−0.0038 (5)	0.0017 (5)
C3	0.0205 (6)	0.0238 (6)	0.0326 (7)	0.0041 (4)	−0.0084 (5)	−0.0072 (5)
C4	0.0168 (5)	0.0139 (5)	0.0223 (5)	0.0009 (4)	−0.0013 (5)	−0.0011 (4)
O5	0.0290 (5)	0.0190 (4)	0.0255 (5)	−0.0002 (4)	0.0042 (4)	0.0039 (3)
C6	0.0137 (5)	0.0184 (5)	0.0224 (6)	0.0028 (4)	0.0012 (4)	−0.0006 (4)
N7	0.0157 (4)	0.0160 (4)	0.0198 (4)	0.0019 (4)	−0.0012 (4)	−0.0016 (3)
C8	0.0153 (5)	0.0344 (6)	0.0253 (6)	−0.0036 (6)	−0.0007 (5)	0.0018 (5)
C9	0.0251 (6)	0.0295 (6)	0.0184 (5)	0.0017 (6)	−0.0008 (5)	0.0000 (4)
C10	0.0339 (7)	0.0153 (5)	0.0396 (7)	0.0063 (5)	−0.0150 (6)	−0.0037 (5)
I11	0.02249 (4)	0.02995 (4)	0.02973 (4)	0.00090 (3)	0.00702 (3)	−0.00501 (3)

Geometric parameters (Å, º)

N1—C2	1.1348 (18)	N7—C8	1.5017 (17)
C2—C3	1.4681 (18)	N7—C9	1.5053 (16)
C3—C4	1.5424 (17)	N7—C10	1.5008 (16)
C3—H32	0.950	C8—H83	0.975
C3—H31	0.948	C8—H82	0.961
C4—O5	1.4134 (15)	C8—H81	0.959
C4—C6	1.5253 (18)	C9—H91	0.954
C4—H41	0.951	C9—H92	0.963
O5—H51	0.804	C9—H93	0.960
C6—N7	1.5114 (15)	C10—H101	0.974
C6—H61	0.962	C10—H103	0.982
C6—H62	0.952	C10—H102	0.962
N1—C2—C3	177.37 (15)	C8—N7—C9	107.89 (10)
C2—C3—C4	112.16 (11)	C6—N7—C10	111.66 (9)
C2—C3—H32	108.8	C8—N7—C10	108.82 (10)
C4—C3—H32	108.6	C9—N7—C10	108.44 (10)
C2—C3—H31	108.5	N7—C8—H83	108.9
C4—C3—H31	112.2	N7—C8—H82	106.6
H32—C3—H31	106.4	H83—C8—H82	108.9
C3—C4—O5	109.63 (10)	N7—C8—H81	108.6
C3—C4—C6	109.49 (10)	H83—C8—H81	111.4
O5—C4—C6	109.89 (10)	H82—C8—H81	112.2
C3—C4—H41	108.1	N7—C9—H91	107.9
O5—C4—H41	110.1	N7—C9—H92	107.4
C6—C4—H41	109.6	H91—C9—H92	112.0
C4—O5—H51	106.3	N7—C9—H93	107.8
C4—C6—N7	115.94 (10)	H91—C9—H93	112.0
C4—C6—H61	107.9	H92—C9—H93	109.6
N7—C6—H61	105.0	N7—C10—H101	107.0
C4—C6—H62	110.5	N7—C10—H103	109.6
N7—C6—H62	107.2	H101—C10—H103	108.8
H61—C6—H62	110.0	N7—C10—H102	108.8
C6—N7—C8	112.58 (9)	H101—C10—H102	110.4
C6—N7—C9	107.30 (10)	H103—C10—H102	112.2

(Rcarnitinenitrile2tetrafluoroborate1chloride1)

Crystal data

2(C7H15N2O)·BF4·Cl	F(000) = 864.000
Mr = 408.67	Dx = 1.307 Mg m^−3
Orthorhombic, P212121	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: P 2ac 2ab	Cell parameters from 13634 reflections
a = 9.4006 (1) Å	θ = 4–79°
b = 13.2619 (2) Å	µ = 2.09 mm^−1
c = 16.6581 (2) Å	T = 160 K
V = 2076.76 (5) Å^3	Block, colorless
Z = 4	0.13 × 0.07 × 0.05 mm

Data collection

Oxford Diffraction SuperNova diffractometer	3958 reflections with I > 2.0σ(I)
Graphite monochromator	Rint = 0.037
ω scans	θmax = 74.5°, θmin = 4.3°
Absorption correction: multi-scan CrysAlisPro, (Agilent, 2011)	h = −11→10
Tmin = 0.75, Tmax = 0.90	k = −16→16
22105 measured reflections	l = −20→20
4175 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: difference Fourier map
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.033	Method = Modified Sheldrick w = 1/[σ^2(F^2) + ( 0.06P)^2 + 0.47P] , where P = (max(Fo^2,0) + 2Fc^2)/3
wR(F^2) = 0.090	(Δ/σ)max = 0.0003
S = 1.00	Δρmax = 0.34 e Å^−3
4175 reflections	Δρmin = −0.19 e Å^−3
264 parameters	Absolute structure: Flack (1983), 1797 Friedel-pairs
19 restraints	Absolute structure parameter: 0.015 (13)
Primary atom site location: Other

Special details

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1K.

Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
F1	−0.06770 (15)	0.67840 (12)	0.47040 (8)	0.0544
F2	0.0796 (3)	0.75743 (13)	0.38243 (17)	0.0813	0.853 (3)
F3	−0.0505 (2)	0.62500 (17)	0.34243 (10)	0.0647	0.853 (3)
F4	0.1322 (2)	0.60123 (17)	0.42603 (15)	0.0609	0.853 (3)
N1	0.2576 (2)	0.47251 (18)	0.66214 (12)	0.0550
C2	0.1678 (2)	0.45723 (15)	0.61760 (11)	0.0369
C3	0.0521 (2)	0.43916 (14)	0.56122 (10)	0.0328
C4	0.10122 (19)	0.37465 (13)	0.48955 (10)	0.0262
O5	0.15963 (15)	0.28203 (10)	0.51708 (8)	0.0350
C6	−0.02928 (18)	0.36130 (13)	0.43668 (9)	0.0259
N7	−0.00343 (14)	0.32273 (11)	0.35235 (8)	0.0242
C8	0.0882 (2)	0.39228 (15)	0.30472 (11)	0.0340
C9	0.0626 (3)	0.21973 (14)	0.35305 (12)	0.0422
C10	−0.1463 (2)	0.31701 (19)	0.31252 (12)	0.0416
N11	0.7337 (2)	0.50357 (16)	0.64934 (12)	0.0511
C12	0.6470 (2)	0.51886 (15)	0.60329 (11)	0.0376
C13	0.5363 (2)	0.54103 (14)	0.54405 (11)	0.0332
C14	0.60284 (19)	0.57765 (12)	0.46486 (10)	0.0252
O15	0.67869 (14)	0.49861 (10)	0.42738 (8)	0.0333
C16	0.48206 (18)	0.61990 (13)	0.41427 (10)	0.0243
N17	0.52589 (15)	0.67854 (11)	0.34012 (8)	0.0249
C18	0.6206 (2)	0.76546 (15)	0.36065 (12)	0.0362
C19	0.3921 (2)	0.71857 (19)	0.30362 (13)	0.0432
C20	0.5990 (2)	0.61400 (16)	0.27927 (11)	0.0365
Cl21	0.45198 (5)	0.33936 (3)	0.37601 (3)	0.0355
B22	0.0246 (2)	0.66776 (16)	0.40679 (12)	0.0324
H41	0.1742	0.4090	0.4611	0.0315*
H61	−0.0728	0.4292	0.4330	0.0312*
H62	−0.0952	0.3168	0.4658	0.0317*
H82	0.0911	0.3673	0.2491	0.0503*
H81	0.0435	0.4587	0.3062	0.0504*
H83	0.1846	0.3946	0.3270	0.0496*
H101	−0.1346	0.2929	0.2564	0.0628*
H103	−0.1911	0.3834	0.3103	0.0625*
H102	−0.2073	0.2725	0.3423	0.0629*
H93	0.0708	0.1954	0.2973	0.0631*
H91	0.0038	0.1768	0.3810	0.0634*
H92	0.1570	0.2201	0.3786	0.0637*
H32	−0.0251	0.4059	0.5898	0.0406*
H31	0.0210	0.5000	0.5394	0.0405*
H141	0.6714	0.6321	0.4776	0.0323*
H161	0.4194	0.5614	0.3965	0.0304*
H162	0.4253	0.6655	0.4495	0.0293*
H181	0.6337	0.8063	0.3143	0.0520*
H182	0.7147	0.7407	0.3749	0.0532*
H183	0.5851	0.8020	0.4046	0.0529*
H202	0.6117	0.6511	0.2291	0.0541*
H201	0.5423	0.5543	0.2682	0.0546*
H203	0.6905	0.5897	0.2983	0.0545*
H193	0.4184	0.7545	0.2548	0.0657*
H192	0.3260	0.6641	0.2927	0.0656*
H191	0.3471	0.7638	0.3413	0.0655*
H131	0.4761	0.4822	0.5324	0.0404*
H132	0.4796	0.5955	0.5694	0.0402*
H151	0.6130	0.4604	0.4099	0.0541*
H51	0.0943	0.2563	0.5466	0.0556*
F5	0.1456 (10)	0.7275 (8)	0.4392 (7)	0.0542	0.147 (3)
F6	0.069 (2)	0.5855 (10)	0.3898 (10)	0.0841	0.147 (3)
F7	−0.0210 (18)	0.7259 (12)	0.3509 (8)	0.0848	0.147 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0428 (7)	0.0784 (9)	0.0419 (6)	−0.0138 (7)	0.0102 (5)	−0.0156 (6)
F2	0.1003 (19)	0.0321 (8)	0.111 (2)	−0.0077 (10)	0.0503 (18)	0.0077 (10)
F3	0.0564 (10)	0.0951 (15)	0.0425 (8)	0.0105 (10)	−0.0081 (7)	−0.0237 (8)
F4	0.0402 (10)	0.0664 (12)	0.0761 (13)	0.0114 (8)	−0.0053 (8)	0.0189 (10)
N1	0.0565 (12)	0.0704 (14)	0.0379 (10)	−0.0164 (10)	−0.0041 (9)	−0.0102 (10)
C2	0.0461 (11)	0.0384 (10)	0.0261 (8)	−0.0072 (8)	0.0042 (8)	−0.0029 (8)
C3	0.0364 (10)	0.0365 (9)	0.0255 (8)	0.0003 (8)	−0.0005 (8)	−0.0020 (7)
C4	0.0255 (8)	0.0293 (8)	0.0237 (7)	0.0011 (7)	0.0010 (6)	0.0008 (6)
O5	0.0318 (7)	0.0373 (7)	0.0358 (7)	0.0078 (5)	−0.0024 (5)	0.0049 (6)
C6	0.0237 (9)	0.0296 (8)	0.0243 (7)	0.0009 (6)	0.0017 (6)	−0.0013 (6)
N7	0.0222 (7)	0.0256 (7)	0.0248 (6)	−0.0014 (5)	−0.0017 (5)	−0.0009 (5)
C8	0.0356 (10)	0.0393 (10)	0.0272 (8)	−0.0070 (8)	0.0040 (7)	0.0024 (7)
C9	0.0604 (14)	0.0263 (8)	0.0398 (10)	0.0072 (9)	−0.0028 (9)	−0.0046 (8)
C10	0.0250 (9)	0.0663 (14)	0.0336 (9)	−0.0063 (9)	−0.0064 (7)	−0.0050 (9)
N11	0.0621 (13)	0.0528 (11)	0.0386 (9)	0.0115 (10)	−0.0110 (9)	0.0094 (9)
C12	0.0503 (12)	0.0331 (9)	0.0293 (9)	0.0029 (8)	−0.0004 (8)	0.0065 (7)
C13	0.0365 (11)	0.0344 (8)	0.0286 (8)	0.0004 (8)	−0.0004 (8)	0.0055 (7)
C14	0.0249 (8)	0.0236 (7)	0.0269 (8)	0.0006 (6)	−0.0014 (7)	0.0019 (6)
O15	0.0264 (7)	0.0323 (7)	0.0413 (7)	0.0070 (5)	0.0003 (5)	−0.0015 (5)
C16	0.0204 (8)	0.0271 (7)	0.0254 (7)	0.0007 (6)	0.0021 (6)	0.0030 (6)
N17	0.0228 (7)	0.0290 (7)	0.0228 (6)	0.0041 (6)	0.0004 (5)	0.0014 (5)
C18	0.0432 (11)	0.0322 (9)	0.0331 (9)	−0.0076 (8)	0.0023 (8)	0.0037 (7)
C19	0.0288 (10)	0.0609 (13)	0.0400 (10)	0.0135 (9)	−0.0017 (8)	0.0190 (10)
C20	0.0418 (11)	0.0429 (10)	0.0247 (8)	0.0078 (9)	0.0028 (7)	−0.0048 (8)
Cl21	0.0320 (2)	0.0345 (2)	0.0401 (2)	0.00079 (17)	−0.00299 (17)	−0.00389 (18)
B22	0.0340 (11)	0.031 (1)	0.0319 (9)	−0.0033 (9)	0.0033 (8)	0.0036 (8)
F5	0.032 (5)	0.060 (5)	0.070 (6)	−0.013 (4)	0.008 (4)	−0.006 (5)
F6	0.111 (8)	0.057 (6)	0.084 (7)	0.009 (6)	0.013 (7)	−0.014 (6)
F7	0.104 (8)	0.086 (7)	0.065 (6)	0.013 (6)	0.008 (6)	0.048 (5)

Geometric parameters (Å, º)

F1—B22	1.377 (2)	N11—C12	1.137 (3)
F2—B22	1.359 (3)	C12—C13	1.464 (3)
F3—B22	1.403 (3)	C13—C14	1.539 (2)
F4—B22	1.380 (3)	C13—H131	0.983
N1—C2	1.142 (3)	C13—H132	0.992
C2—C3	1.457 (3)	C14—O15	1.413 (2)
C3—C4	1.540 (2)	C14—C16	1.521 (2)
C3—H32	0.974	C14—H141	0.991
C3—H31	0.931	O15—H151	0.851
C4—O5	1.421 (2)	C16—N17	1.517 (2)
C4—C6	1.520 (2)	C16—H161	1.018
C4—H41	0.949	C16—H162	0.997
O5—H51	0.857	N17—C18	1.496 (2)
C6—N7	1.515 (2)	N17—C19	1.494 (2)
C6—H61	0.991	N17—C20	1.494 (2)
C6—H62	0.984	C18—H181	0.951
N7—C8	1.491 (2)	C18—H182	0.973
N7—C9	1.501 (2)	C18—H183	0.939
N7—C10	1.500 (2)	C19—H193	0.974
C8—H82	0.984	C19—H192	0.970
C8—H81	0.976	C19—H191	0.966
C8—H83	0.980	C20—H202	0.977
C9—H93	0.986	C20—H201	0.972
C9—H91	0.920	C20—H203	0.972
C9—H92	0.984	B22—F5	1.488 (10)
C10—H101	0.995	B22—F6	1.201 (13)
C10—H103	0.977	B22—F7	1.282 (11)
C10—H102	0.961
N1—C2—C3	179.1 (2)	H131—C13—H132	110.7
C2—C3—C4	111.56 (17)	C13—C14—O15	110.48 (14)
C2—C3—H32	108.4	C13—C14—C16	106.72 (14)
C4—C3—H32	110.5	O15—C14—C16	113.89 (14)
C2—C3—H31	110.1	C13—C14—H141	108.1
C4—C3—H31	105.9	O15—C14—H141	107.9
H32—C3—H31	110.4	C16—C14—H141	109.6
C3—C4—O5	110.22 (14)	C14—O15—H151	103.1
C3—C4—C6	105.78 (14)	C14—C16—N17	115.94 (14)
O5—C4—C6	113.45 (14)	C14—C16—H161	108.2
C3—C4—H41	109.7	N17—C16—H161	108.2
O5—C4—H41	107.2	C14—C16—H162	107.2
C6—C4—H41	110.5	N17—C16—H162	108.3
C4—O5—H51	104.6	H161—C16—H162	108.8
C4—C6—N7	116.55 (14)	C16—N17—C18	111.75 (13)
C4—C6—H61	105.2	C16—N17—C19	106.56 (13)
N7—C6—H61	108.4	C18—N17—C19	108.66 (16)
C4—C6—H62	107.0	C16—N17—C20	112.57 (14)
N7—C6—H62	110.8	C18—N17—C20	108.82 (14)
H61—C6—H62	108.5	C19—N17—C20	108.34 (15)
C6—N7—C8	112.17 (13)	N17—C18—H181	109.3
C6—N7—C9	111.51 (13)	N17—C18—H182	109.7
C8—N7—C9	109.16 (15)	H181—C18—H182	105.8
C6—N7—C10	106.48 (13)	N17—C18—H183	111.4
C8—N7—C10	108.26 (14)	H181—C18—H183	112.6
C9—N7—C10	109.15 (16)	H182—C18—H183	107.9
N7—C8—H82	108.0	N17—C19—H193	107.4
N7—C8—H81	107.2	N17—C19—H192	110.6
H82—C8—H81	109.8	H193—C19—H192	111.7
N7—C8—H83	110.7	N17—C19—H191	109.0
H82—C8—H83	110.0	H193—C19—H191	110.4
H81—C8—H83	111.1	H192—C19—H191	107.7
N7—C9—H93	108.9	N17—C20—H202	110.4
N7—C9—H91	108.6	N17—C20—H201	110.1
H93—C9—H91	108.7	H202—C20—H201	108.3
N7—C9—H92	111.9	N17—C20—H203	112.1
H93—C9—H92	109.8	H202—C20—H203	109.7
H91—C9—H92	108.9	H201—C20—H203	106.1
N7—C10—H101	109.4	F1—B22—F5	98.5 (4)
N7—C10—H103	110.9	F1—B22—F6	119.5 (7)
H101—C10—H103	107.5	F5—B22—F6	107.8 (11)
N7—C10—H102	109.7	F1—B22—F7	106.6 (7)
H101—C10—H102	110.8	F5—B22—F7	101.5 (10)
H103—C10—H102	108.5	F6—B22—F7	119.4 (11)
N11—C12—C13	178.7 (2)	F3—B22—F4	106.7 (2)
C12—C13—C14	110.59 (16)	F3—B22—F1	108.21 (17)
C12—C13—H131	112.5	F4—B22—F1	110.41 (18)
C14—C13—H131	108.4	F3—B22—F2	108.5 (2)
C12—C13—H132	104.0	F4—B22—F2	110.5 (2)
C14—C13—H132	110.7	F1—B22—F2	112.34 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H61···O15^i	0.99	2.51	3.298 (3)	136

Symmetry code: (i) x−1, y, z.

(Diltiazembromide)

Crystal data

C22H27N2O4S·Br	F(000) = 1024
Mr = 495.44	Dx = 1.410 Mg m^−3
Orthorhombic, P212121	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5919 reflections
a = 6.1060 (3) Å	θ = 5–78°
b = 9.0317 (6) Å	µ = 3.48 mm^−1
c = 42.330 (4) Å	T = 160 K
V = 2334.4 (3) Å^3	Plate, colorless
Z = 4	0.07 × 0.04 × 0.01 mm

Data collection

Oxford Diffraction SuperNova diffractometer	4199 reflections with I > 2.0σ(I)
Graphite monochromator	Rint = 0.102
ω scans	θmax = 74.5°, θmin = 4.2°
Absorption correction: multi-scan CrysAlisPro, (Agilent, 2011)	h = −7→7
Tmin = 0.69, Tmax = 0.95	k = −11→10
24363 measured reflections	l = −52→52
4772 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: difference Fourier map
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.067	Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)] where Ai are the Chebychev coefficients listed below and x = F /Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2]^2 Ai are: 29.0 23.1 9.35
wR(F^2) = 0.092	(Δ/σ)max = 0.002
S = 1.09	Δρmax = 0.93 e Å^−3
4772 reflections	Δρmin = −0.72 e Å^−3
272 parameters	Absolute structure: Flack (1983), 1977 Friedel-pairs
0 restraints	Absolute structure parameter: −0.04 (3)
Primary atom site location: Other

Special details

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1K.

Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	−0.0196 (3)	0.16071 (18)	0.58505 (4)	0.0428
C2	0.1067 (9)	0.1066 (8)	0.62127 (14)	0.0374
C3	0.1757 (11)	−0.0332 (8)	0.62539 (18)	0.0442
C4	0.2736 (12)	−0.0799 (8)	0.65363 (16)	0.0483
C5	0.2981 (12)	0.0226 (8)	0.67763 (18)	0.0478
C6	0.2283 (11)	0.1644 (8)	0.67375 (17)	0.0394
C7	0.1299 (10)	0.2103 (7)	0.64579 (15)	0.0321
N8	0.0507 (7)	0.3563 (5)	0.64275 (10)	0.0290
C9	−0.0934 (9)	0.4188 (7)	0.66718 (13)	0.0294
C10	0.0286 (10)	0.5280 (6)	0.68756 (13)	0.0312
N11	−0.1185 (7)	0.6150 (6)	0.70871 (10)	0.0275
C12	−0.2436 (11)	0.7306 (7)	0.69168 (16)	0.0385
C13	0.0065 (12)	0.6818 (6)	0.73561 (14)	0.0452
C14	0.0917 (9)	0.4459 (7)	0.61721 (14)	0.0306
O15	0.0096 (8)	0.5654 (4)	0.61337 (8)	0.0353
C16	0.2702 (9)	0.3849 (8)	0.59466 (14)	0.0321
O17	0.3822 (6)	0.5117 (5)	0.58050 (10)	0.0374
C18	0.4840 (10)	0.6029 (8)	0.60184 (13)	0.0365
O19	0.4773 (8)	0.5760 (5)	0.62998 (9)	0.0408
C20	0.5967 (10)	0.7309 (7)	0.58725 (15)	0.0403
C21	0.1802 (10)	0.2881 (7)	0.56829 (15)	0.0374
C22	0.0745 (10)	0.3688 (8)	0.54052 (15)	0.0367
C23	−0.1281 (10)	0.4362 (7)	0.54301 (15)	0.0347
C24	−0.2245 (10)	0.5101 (8)	0.51794 (15)	0.0347
C25	−0.1192 (10)	0.5144 (6)	0.48912 (14)	0.0246
C26	0.0829 (9)	0.4457 (6)	0.48617 (15)	0.0270
C27	0.1755 (9)	0.3733 (7)	0.51119 (15)	0.0324
O28	−0.1984 (6)	0.5869 (6)	0.46312 (9)	0.0388
C29	−0.3813 (11)	0.6810 (7)	0.46722 (16)	0.0426
Br30	0.52050 (10)	0.39795 (8)	0.736573 (16)	0.0398
H293	−0.4059	0.7362	0.4482	0.0628*
H292	−0.5079	0.6224	0.4720	0.0628*
H291	−0.3538	0.7486	0.4840	0.0629*
H231	−0.2024	0.4307	0.5623	0.0398*
H241	−0.3601	0.5565	0.5205	0.0408*
H261	0.1532	0.4486	0.4669	0.0372*
H271	0.3100	0.3252	0.5087	0.0413*
H211	0.3022	0.2291	0.5601	0.0421*
H203	0.5795	0.8166	0.6003	0.0632*
H202	0.7487	0.7094	0.5848	0.0631*
H201	0.5336	0.7494	0.5670	0.0631*
H161	0.3775	0.3285	0.6069	0.0409*
H133	−0.0917	0.7331	0.7493	0.0719*
H132	0.1124	0.7505	0.7276	0.0718*
H131	0.0790	0.6058	0.7472	0.0718*
H123	−0.3501	0.7737	0.7058	0.0591*
H122	−0.3167	0.6887	0.6738	0.0590*
H121	−0.1439	0.8067	0.6848	0.0588*
H111	−0.2151	0.5524	0.7170	0.0421*
H102	0.1035	0.5980	0.6739	0.0370*
H101	0.1329	0.4752	0.7002	0.0371*
H92	−0.2162	0.4669	0.6572	0.0360*
H91	−0.1442	0.3371	0.6802	0.0360*
H31	0.1577	−0.1011	0.6090	0.0510*
H41	0.3202	−0.1767	0.6561	0.0571*
H51	0.3646	−0.0047	0.6966	0.0598*
H61	0.2472	0.2329	0.6900	0.0501*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0438 (10)	0.0469 (10)	0.0376 (8)	0.0019 (10)	−0.0078 (10)	−0.0077 (7)
C2	0.033 (3)	0.037 (4)	0.043 (4)	0.008 (3)	0.001 (3)	−0.001 (4)
C3	0.046 (4)	0.032 (4)	0.055 (5)	0.004 (3)	0.002 (4)	−0.006 (4)
C4	0.058 (5)	0.034 (5)	0.052 (5)	0.012 (4)	0.002 (4)	−0.006 (4)
C5	0.053 (5)	0.046 (5)	0.044 (4)	0.025 (4)	−0.005 (4)	0.004 (4)
C6	0.043 (4)	0.037 (4)	0.038 (4)	0.001 (3)	−0.001 (3)	−0.007 (3)
C7	0.032 (3)	0.034 (4)	0.031 (4)	0.006 (3)	0.002 (3)	−0.002 (3)
N8	0.025 (3)	0.035 (3)	0.026 (2)	0.010 (2)	−0.003 (2)	−0.005 (2)
C9	0.026 (3)	0.028 (4)	0.035 (3)	0.009 (3)	−0.002 (2)	−0.004 (3)
C10	0.024 (3)	0.029 (3)	0.041 (3)	0.007 (3)	0.005 (3)	−0.005 (3)
N11	0.026 (2)	0.025 (3)	0.032 (3)	0.003 (2)	0.000 (2)	−0.005 (3)
C12	0.043 (4)	0.026 (4)	0.047 (4)	0.015 (3)	−0.001 (3)	−0.003 (3)
C13	0.035 (3)	0.061 (4)	0.040 (3)	0.014 (4)	−0.009 (4)	−0.023 (3)
C14	0.018 (3)	0.041 (4)	0.032 (3)	0.006 (3)	−0.004 (2)	−0.012 (3)
O15	0.030 (2)	0.039 (3)	0.037 (2)	0.016 (3)	0.003 (2)	0.0013 (18)
C16	0.029 (3)	0.030 (4)	0.037 (3)	0.010 (3)	0.000 (3)	−0.005 (3)
O17	0.027 (2)	0.045 (3)	0.041 (3)	0.009 (2)	0.000 (2)	−0.008 (2)
C18	0.020 (3)	0.045 (3)	0.044 (3)	0.014 (4)	−0.002 (3)	−0.012 (3)
O19	0.032 (2)	0.050 (3)	0.040 (2)	0.004 (3)	−0.003 (2)	0.000 (2)
C20	0.030 (4)	0.042 (4)	0.049 (4)	0.008 (3)	−0.002 (3)	0.007 (4)
C21	0.035 (4)	0.041 (4)	0.036 (4)	0.016 (3)	−0.001 (3)	−0.009 (3)
C22	0.032 (4)	0.049 (5)	0.029 (3)	0.011 (3)	−0.005 (3)	−0.009 (3)
C23	0.034 (3)	0.041 (4)	0.029 (4)	0.009 (3)	0.002 (3)	−0.006 (3)
C24	0.025 (3)	0.039 (4)	0.041 (4)	0.005 (3)	−0.002 (3)	0.000 (3)
C25	0.030 (3)	0.012 (3)	0.031 (3)	−0.001 (2)	−0.003 (3)	0.001 (3)
C26	0.027 (3)	0.015 (3)	0.038 (4)	−0.003 (2)	0.007 (3)	−0.003 (3)
C27	0.023 (3)	0.030 (4)	0.044 (4)	0.006 (3)	−0.002 (3)	−0.006 (3)
O28	0.037 (2)	0.047 (3)	0.033 (2)	0.008 (2)	0.0041 (19)	0.009 (2)
C29	0.038 (4)	0.046 (5)	0.044 (4)	0.009 (4)	−0.004 (3)	0.007 (4)
Br30	0.0287 (3)	0.0486 (4)	0.0422 (3)	−0.0043 (4)	−0.0020 (3)	0.0052 (4)

Geometric parameters (Å, º)

S1—C2	1.785 (6)	C13—H131	0.954
S1—C21	1.820 (7)	C14—O15	1.202 (7)
C2—C3	1.342 (9)	C14—C16	1.550 (7)
C2—C7	1.405 (9)	C16—O17	1.462 (7)
C3—C4	1.402 (9)	C16—C21	1.521 (8)
C3—H31	0.933	C16—H161	0.979
C4—C5	1.382 (9)	O17—C18	1.372 (7)
C4—H41	0.925	C18—O19	1.216 (6)
C5—C6	1.360 (9)	C18—C20	1.480 (9)
C5—H51	0.932	C20—H203	0.956
C6—C7	1.390 (9)	C20—H202	0.954
C6—H61	0.933	C20—H201	0.953
C7—N8	1.411 (7)	C21—C22	1.527 (9)
N8—C9	1.470 (6)	C21—H211	0.980
N8—C14	1.373 (7)	C22—C23	1.382 (8)
C9—C10	1.507 (7)	C22—C27	1.387 (8)
C9—H92	0.964	C23—C24	1.385 (9)
C9—H91	0.972	C23—H231	0.936
C10—N11	1.492 (6)	C24—C25	1.380 (8)
C10—H102	0.970	C24—H241	0.934
C10—H101	0.958	C25—C26	1.387 (7)
N11—C12	1.481 (7)	C25—O28	1.369 (7)
N11—C13	1.497 (7)	C26—C27	1.367 (8)
N11—H111	0.889	C26—H261	0.924
C12—H123	0.966	C27—H271	0.935
C12—H122	0.956	O28—C29	1.414 (7)
C12—H121	0.963	C29—H293	0.958
C13—H133	0.953	C29—H292	0.958
C13—H132	0.958	C29—H291	0.952
C2—S1—C21	102.6 (3)	H132—C13—H131	109.6
S1—C2—C3	120.3 (6)	N8—C14—O15	124.0 (5)
S1—C2—C7	119.7 (5)	N8—C14—C16	113.8 (5)
C3—C2—C7	120.0 (6)	O15—C14—C16	122.0 (6)
C2—C3—C4	121.8 (7)	C14—C16—O17	107.7 (5)
C2—C3—H31	119.0	C14—C16—C21	113.7 (5)
C4—C3—H31	119.2	O17—C16—C21	108.6 (5)
C3—C4—C5	118.1 (7)	C14—C16—H161	109.2
C3—C4—H41	120.8	O17—C16—H161	108.1
C5—C4—H41	121.1	C21—C16—H161	109.4
C4—C5—C6	120.6 (7)	C16—O17—C18	114.3 (5)
C4—C5—H51	120.1	O17—C18—O19	120.6 (6)
C6—C5—H51	119.3	O17—C18—C20	113.9 (5)
C5—C6—C7	121.2 (7)	O19—C18—C20	125.5 (6)
C5—C6—H61	119.8	C18—C20—H203	109.9
C7—C6—H61	119.0	C18—C20—H202	109.8
C2—C7—C6	118.3 (6)	H203—C20—H202	109.5
C2—C7—N8	121.4 (6)	C18—C20—H201	108.9
C6—C7—N8	120.3 (6)	H203—C20—H201	109.4
C7—N8—C9	120.0 (5)	H202—C20—H201	109.4
C7—N8—C14	124.0 (5)	C16—C21—S1	108.6 (4)
C9—N8—C14	115.9 (5)	C16—C21—C22	116.3 (6)
N8—C9—C10	111.0 (4)	S1—C21—C22	108.6 (4)
N8—C9—H92	109.2	C16—C21—H211	107.4
C10—C9—H92	109.9	S1—C21—H211	107.8
N8—C9—H91	107.4	C22—C21—H211	107.9
C10—C9—H91	109.3	C21—C22—C23	122.0 (6)
H92—C9—H91	110.0	C21—C22—C27	121.0 (5)
C9—C10—N11	113.0 (5)	C23—C22—C27	117.0 (6)
C9—C10—H102	108.6	C22—C23—C24	122.3 (7)
N11—C10—H102	107.3	C22—C23—H231	118.5
C9—C10—H101	108.8	C24—C23—H231	119.2
N11—C10—H101	109.1	C23—C24—C25	119.5 (6)
H102—C10—H101	110.0	C23—C24—H241	120.2
C10—N11—C12	112.9 (4)	C25—C24—H241	120.2
C10—N11—C13	111.2 (4)	C24—C25—C26	118.8 (6)
C12—N11—C13	110.4 (5)	C24—C25—O28	124.0 (5)
C10—N11—H111	107.5	C26—C25—O28	117.1 (6)
C12—N11—H111	107.3	C25—C26—C27	120.8 (6)
C13—N11—H111	107.1	C25—C26—H261	118.7
N11—C12—H123	109.2	C27—C26—H261	120.4
N11—C12—H122	110.3	C22—C27—C26	121.6 (6)
H123—C12—H122	109.5	C22—C27—H271	118.6
N11—C12—H121	108.9	C26—C27—H271	119.9
H123—C12—H121	109.1	C25—O28—C29	117.9 (5)
H122—C12—H121	109.7	O28—C29—H293	109.5
N11—C13—H133	109.7	O28—C29—H292	109.3
N11—C13—H132	109.6	H293—C29—H292	109.8
H133—C13—H132	108.9	O28—C29—H291	109.8
N11—C13—H131	109.9	H293—C29—H291	108.7
H133—C13—H131	109.2	H292—C29—H291	109.8

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C20—H202···O15^i	0.95	2.38	3.132 (9)	135
C20—H201···O28^ii	0.95	2.41	3.241 (9)	145
C12—H122···O19^iii	0.96	2.46	3.417 (9)	177
C9—H92···O19^iii	0.96	2.41	3.372 (9)	177

Symmetry codes: (i) x+1, y, z; (ii) x+1/2, −y+3/2, −z+1; (iii) x−1, y, z.

(Diltiazemiodide)

Crystal data

C22H27N2O4S·I	F(000) = 1096
Mr = 542.44	Dx = 1.490 Mg m^−3
Orthorhombic, P212121	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: P 2ac 2ab	Cell parameters from 13159 reflections
a = 6.2219 (1) Å	θ = 4–79°
b = 9.0228 (1) Å	µ = 11.46 mm^−1
c = 43.0569 (5) Å	T = 160 K
V = 2417.17 (5) Å^3	Prism, colorless
Z = 4	0.39 × 0.05 × 0.03 mm

Data collection

Oxford Diffraction SuperNova diffractometer	4860 reflections with I > 2.0σ(I)
Graphite monochromator	Rint = 0.030
ω scans	θmax = 74.5°, θmin = 4.1°
Absorption correction: multi-scan CrysAlisPro, (Agilent, 2011)	h = −7→7
Tmin = 0.47, Tmax = 0.70	k = −9→11
15587 measured reflections	l = −53→52
4935 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: difference Fourier map
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.021	Method = Modified Sheldrick w = 1/[σ^2(F^2) + ( 0.03P)^2 + 1.04P] , where P = (max(Fo^2,0) + 2Fc^2)/3
wR(F^2) = 0.053	(Δ/σ)max = 0.002
S = 0.99	Δρmax = 0.36 e Å^−3
4935 reflections	Δρmin = −0.37 e Å^−3
272 parameters	Absolute structure: Flack (1983), 2050 Friedel-pairs
0 restraints	Absolute structure parameter: −0.013 (3)
Primary atom site location: structure-invariant direct methods

Special details

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1K.

Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	1.02427 (11)	0.15951 (6)	0.417600 (13)	0.0276
C2	0.8985 (4)	0.1108 (3)	0.38217 (5)	0.0254
C3	0.8229 (5)	−0.0332 (3)	0.37791 (6)	0.0303
C4	0.7301 (5)	−0.0752 (3)	0.34987 (6)	0.0343
C5	0.7125 (5)	0.0256 (3)	0.32594 (6)	0.0337
C6	0.7876 (4)	0.1698 (3)	0.32967 (6)	0.0289
C7	0.8805 (4)	0.2134 (3)	0.35759 (6)	0.0237
N8	0.9596 (3)	0.3606 (2)	0.36116 (4)	0.0214
C9	1.1007 (4)	0.4238 (3)	0.33715 (5)	0.0221
C10	0.9747 (4)	0.5365 (3)	0.31811 (5)	0.0243
N11	1.1161 (3)	0.6262 (2)	0.29716 (4)	0.0218
C12	0.9878 (5)	0.6990 (3)	0.27228 (6)	0.0353
C13	1.2474 (5)	0.7371 (3)	0.31425 (6)	0.0321
C14	0.9148 (4)	0.4476 (3)	0.38623 (5)	0.0207
O15	0.9969 (3)	0.56815 (16)	0.39033 (3)	0.0245
C16	0.7398 (4)	0.3879 (3)	0.40823 (5)	0.0220
O17	0.6276 (3)	0.51100 (19)	0.42194 (4)	0.0234
C18	0.5268 (3)	0.5996 (3)	0.40072 (5)	0.0236
O19	0.5332 (3)	0.57361 (18)	0.37324 (4)	0.0276
C20	0.4120 (4)	0.7260 (3)	0.41545 (6)	0.0289
C21	0.8276 (4)	0.2897 (3)	0.43445 (5)	0.0240
C22	0.9387 (4)	0.3693 (3)	0.46107 (5)	0.0226
C23	0.8368 (4)	0.3766 (3)	0.49003 (5)	0.0225
C24	0.9325 (4)	0.4498 (3)	0.51471 (5)	0.0223
C25	1.1323 (4)	0.5170 (3)	0.51102 (5)	0.0207
C26	1.2378 (4)	0.5077 (3)	0.48268 (6)	0.0230
C27	1.1405 (4)	0.4332 (3)	0.45812 (5)	0.0242
O28	1.2105 (3)	0.5890 (2)	0.53656 (4)	0.0271
C29	1.3943 (4)	0.6818 (3)	0.53234 (6)	0.0312
I30	1.48132 (2)	0.394832 (17)	0.264191 (3)	0.0283
H31	0.8293	−0.1014	0.3946	0.0364*
H41	0.6792	−0.1716	0.3475	0.0405*
H51	0.6519	−0.0015	0.3067	0.0405*
H61	0.7702	0.2375	0.3135	0.0339*
H92	1.2271	0.4704	0.3467	0.0270*
H91	1.1486	0.3436	0.3237	0.0273*
H101	0.9003	0.6034	0.3321	0.0296*
H102	0.8718	0.4869	0.3050	0.0292*
H121	1.0820	0.7558	0.2597	0.0529*
H122	0.8828	0.7612	0.2820	0.0533*
H123	0.9229	0.6244	0.2602	0.0531*
H131	1.3391	0.7860	0.2995	0.0488*
H132	1.3316	0.6882	0.3300	0.0487*
H133	1.1536	0.8087	0.3234	0.0492*
H161	0.6379	0.3309	0.3960	0.0259*
H201	0.3910	0.8033	0.4007	0.0463*
H202	0.4869	0.7638	0.4331	0.0467*
H203	0.2762	0.6905	0.4218	0.0457*
H211	0.7095	0.2310	0.4428	0.0290*
H231	0.7014	0.3318	0.4926	0.0267*
H241	0.8651	0.4560	0.5339	0.0265*
H261	1.3700	0.5509	0.4796	0.0276*
H271	1.2169	0.4250	0.4391	0.0286*
H292	1.4171	0.7329	0.5514	0.0459*
H291	1.5169	0.6195	0.5279	0.0458*
H293	1.3691	0.7492	0.5154	0.0458*
H111	1.2089	0.5655	0.2883	0.0328*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0344 (3)	0.0262 (2)	0.0222 (2)	−0.0002 (3)	−0.0066 (3)	0.00463 (19)
C2	0.0295 (11)	0.0249 (11)	0.0219 (11)	−0.0026 (10)	−0.0027 (9)	0.0038 (10)
C3	0.0368 (14)	0.0221 (12)	0.0322 (13)	−0.0049 (10)	0.0018 (11)	0.0060 (10)
C4	0.0432 (15)	0.0249 (13)	0.0347 (14)	−0.0076 (11)	0.0001 (11)	−0.0033 (11)
C5	0.0391 (15)	0.0319 (14)	0.0300 (13)	−0.0075 (12)	−0.0050 (12)	−0.0065 (11)
C6	0.0374 (14)	0.0292 (13)	0.0201 (11)	−0.0036 (11)	−0.0038 (10)	0.0015 (10)
C7	0.0289 (12)	0.0214 (11)	0.0207 (11)	−0.0032 (9)	−0.0011 (9)	0.0011 (9)
N8	0.0264 (9)	0.0210 (8)	0.0167 (8)	−0.0051 (7)	0.0009 (7)	0.0042 (6)
C9	0.0225 (10)	0.0245 (11)	0.0193 (10)	−0.0016 (9)	0.0021 (8)	0.0045 (9)
C10	0.0200 (11)	0.0300 (11)	0.0230 (10)	−0.0055 (10)	−0.0012 (9)	0.0080 (8)
N11	0.0209 (9)	0.0260 (10)	0.0185 (9)	−0.0017 (8)	0.0004 (7)	0.0046 (8)
C12	0.0323 (13)	0.0429 (14)	0.0307 (12)	−0.0072 (12)	−0.0088 (11)	0.0174 (10)
C13	0.0352 (14)	0.0305 (13)	0.0304 (13)	−0.0111 (11)	−0.0038 (11)	0.0052 (11)
C14	0.0187 (10)	0.0254 (11)	0.0181 (10)	−0.0019 (8)	−0.0037 (8)	0.0049 (8)
O15	0.0246 (8)	0.0255 (7)	0.0234 (7)	−0.0090 (7)	−0.0005 (7)	0.0009 (6)
C16	0.0223 (10)	0.0253 (11)	0.0183 (10)	−0.0046 (10)	−0.0009 (8)	0.0025 (9)
O17	0.0235 (8)	0.0291 (8)	0.0176 (7)	−0.0023 (7)	−0.0012 (6)	0.0029 (6)
C18	0.0185 (10)	0.0284 (10)	0.0240 (10)	−0.0075 (11)	−0.0014 (8)	0.0043 (8)
O19	0.0277 (8)	0.0336 (8)	0.0213 (7)	−0.0007 (7)	−0.0038 (7)	0.0017 (6)
C20	0.0251 (12)	0.0295 (12)	0.0320 (13)	−0.0043 (10)	−0.0010 (10)	−0.0001 (10)
C21	0.0245 (11)	0.0271 (12)	0.0204 (11)	−0.0067 (9)	−0.0024 (9)	0.0054 (9)
C22	0.0248 (11)	0.0253 (11)	0.0178 (10)	−0.0038 (9)	−0.0025 (8)	0.0052 (9)
C23	0.0197 (10)	0.0249 (11)	0.0229 (11)	−0.0004 (9)	0.0011 (8)	0.0066 (9)
C24	0.0229 (11)	0.0244 (10)	0.0195 (10)	0.0029 (9)	0.0045 (8)	0.0036 (8)
C25	0.0238 (11)	0.0189 (10)	0.0195 (10)	0.0034 (9)	−0.0023 (9)	0.0022 (9)
C26	0.0179 (10)	0.0284 (12)	0.0227 (11)	−0.0028 (8)	−0.0007 (9)	0.0045 (9)
C27	0.0261 (11)	0.0302 (12)	0.0162 (10)	−0.0041 (9)	0.0022 (9)	0.0035 (9)
O28	0.0286 (8)	0.0312 (9)	0.0214 (8)	−0.0043 (8)	0.0001 (6)	−0.0034 (7)
C29	0.0296 (13)	0.0334 (13)	0.0306 (13)	−0.0068 (11)	−0.0025 (10)	−0.0011 (11)
I30	0.02538 (7)	0.03403 (8)	0.02551 (7)	0.00332 (6)	−0.00250 (6)	−0.00578 (6)

Geometric parameters (Å, º)

S1—C2	1.770 (2)	C13—H133	0.957
S1—C21	1.845 (3)	C14—O15	1.214 (3)
C2—C3	1.394 (4)	C14—C16	1.540 (3)
C2—C7	1.411 (3)	C16—O17	1.439 (3)
C3—C4	1.391 (4)	C16—C21	1.535 (3)
C3—H31	0.947	C16—H161	0.971
C4—C5	1.379 (4)	O17—C18	1.367 (3)
C4—H41	0.931	C18—O19	1.207 (3)
C5—C6	1.392 (4)	C18—C20	1.488 (3)
C5—H51	0.943	C20—H201	0.953
C6—C7	1.391 (3)	C20—H202	0.953
C6—H61	0.933	C20—H203	0.944
C7—N8	1.425 (3)	C21—C22	1.519 (3)
N8—C9	1.471 (3)	C21—H211	0.975
N8—C14	1.364 (3)	C22—C23	1.400 (3)
C9—C10	1.524 (3)	C22—C27	1.387 (3)
C9—H92	0.981	C23—C24	1.385 (3)
C9—H91	0.974	C23—H231	0.941
C10—N11	1.497 (3)	C24—C25	1.392 (3)
C10—H101	0.970	C24—H241	0.928
C10—H102	0.965	C25—C26	1.388 (3)
N11—C12	1.489 (3)	C25—O28	1.367 (3)
N11—C13	1.487 (3)	C26—C27	1.391 (3)
N11—H111	0.884	C26—H261	0.920
C12—H121	0.948	C27—H271	0.949
C12—H122	0.958	O28—C29	1.429 (3)
C12—H123	0.942	C29—H292	0.953
C13—H131	0.959	C29—H291	0.966
C13—H132	0.964	C29—H293	0.963
C2—S1—C21	101.76 (11)	H132—C13—H133	110.5
S1—C2—C3	119.62 (19)	N8—C14—O15	123.0 (2)
S1—C2—C7	121.22 (19)	N8—C14—C16	115.46 (19)
C3—C2—C7	119.1 (2)	O15—C14—C16	121.4 (2)
C2—C3—C4	120.5 (2)	C14—C16—O17	108.97 (19)
C2—C3—H31	119.4	C14—C16—C21	113.77 (19)
C4—C3—H31	120.0	O17—C16—C21	108.44 (17)
C3—C4—C5	120.1 (2)	C14—C16—H161	108.3
C3—C4—H41	119.3	O17—C16—H161	108.3
C5—C4—H41	120.5	C21—C16—H161	109.0
C4—C5—C6	120.3 (2)	C16—O17—C18	113.60 (17)
C4—C5—H51	121.2	O17—C18—O19	121.8 (2)
C6—C5—H51	118.5	O17—C18—C20	112.58 (19)
C5—C6—C7	120.2 (2)	O19—C18—C20	125.7 (2)
C5—C6—H61	119.1	C18—C20—H201	110.0
C7—C6—H61	120.6	C18—C20—H202	112.2
C2—C7—C6	119.7 (2)	H201—C20—H202	109.7
C2—C7—N8	120.3 (2)	C18—C20—H203	107.0
C6—C7—N8	120.0 (2)	H201—C20—H203	108.6
C7—N8—C9	119.45 (18)	H202—C20—H203	109.2
C7—N8—C14	123.46 (19)	C16—C21—S1	108.29 (16)
C9—N8—C14	117.08 (18)	C16—C21—C22	116.4 (2)
N8—C9—C10	109.24 (18)	S1—C21—C22	107.21 (16)
N8—C9—H92	110.5	C16—C21—H211	108.5
C10—C9—H92	110.6	S1—C21—H211	107.4
N8—C9—H91	108.2	C22—C21—H211	108.7
C10—C9—H91	109.5	C21—C22—C23	119.2 (2)
H92—C9—H91	108.8	C21—C22—C27	122.6 (2)
C9—C10—N11	112.48 (19)	C23—C22—C27	118.1 (2)
C9—C10—H101	109.0	C22—C23—C24	120.7 (2)
N11—C10—H101	108.6	C22—C23—H231	119.2
C9—C10—H102	110.3	C24—C23—H231	120.0
N11—C10—H102	106.7	C23—C24—C25	120.3 (2)
H101—C10—H102	109.7	C23—C24—H241	121.1
C10—N11—C12	110.91 (18)	C25—C24—H241	118.6
C10—N11—C13	112.86 (18)	C24—C25—C26	119.7 (2)
C12—N11—C13	110.7 (2)	C24—C25—O28	115.7 (2)
C10—N11—H111	108.1	C26—C25—O28	124.6 (2)
C12—N11—H111	108.2	C25—C26—C27	119.4 (2)
C13—N11—H111	105.8	C25—C26—H261	121.5
N11—C12—H121	108.5	C27—C26—H261	119.0
N11—C12—H122	108.1	C26—C27—C22	121.7 (2)
H121—C12—H122	110.7	C26—C27—H271	118.4
N11—C12—H123	108.3	C22—C27—H271	120.0
H121—C12—H123	109.6	C25—O28—C29	117.46 (19)
H122—C12—H123	111.6	O28—C29—H292	107.0
N11—C13—H131	108.0	O28—C29—H291	108.4
N11—C13—H132	109.8	H292—C29—H291	109.5
H131—C13—H132	110.6	O28—C29—H293	109.7
N11—C13—H133	108.9	H292—C29—H293	111.9
H131—C13—H133	109.0	H291—C29—H293	110.3

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H92···O19^i	0.98	2.41	3.388 (4)	176
C13—H132···O19^i	0.96	2.47	3.434 (4)	176
C20—H202···O28^ii	0.95	2.33	3.241 (4)	161
C20—H203···O15^iii	0.94	2.46	3.142 (4)	129

Symmetry codes: (i) x+1, y, z; (ii) x−1/2, −y+3/2, −z+1; (iii) x−1, y, z.

(Diltiazemnitrate)

Crystal data

C22H27N2O4S·NO3	F(000) = 1008
Mr = 477.54	Dx = 1.314 Mg m^−3
Orthorhombic, P212121	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: P 2ac 2ab	Cell parameters from 11950 reflections
a = 6.3765 (1) Å	θ = 4–78°
b = 8.8174 (1) Å	µ = 1.59 mm^−1
c = 42.9420 (7) Å	T = 160 K
V = 2414.38 (6) Å^3	Prism, colorless
Z = 4	0.62 × 0.05 × 0.03 mm

Data collection

Oxford Diffraction SuperNova diffractometer	4641 reflections with I > 2.0σ(I)
Graphite monochromator	Rint = 0.051
ω scans	θmax = 74.5°, θmin = 4.1°
Absorption correction: multi-scan CrysAlisPro, (Agilent, 2011)	h = −7→7
Tmin = 0.58, Tmax = 0.96	k = −11→10
25295 measured reflections	l = −53→53
4925 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: difference Fourier map
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.039	Method = Modified Sheldrick w = 1/[σ^2(F^2) + ( 0.04P)^2 + 1.44P] , where P = (max(Fo^2,0) + 2Fc^2)/3
wR(F^2) = 0.093	(Δ/σ)max = 0.001
S = 0.99	Δρmax = 0.35 e Å^−3
4925 reflections	Δρmin = −0.26 e Å^−3
299 parameters	Absolute structure: Flack (1983), 2051 Friedel-pairs
0 restraints	Absolute structure parameter: 0.030 (18)
Primary atom site location: Other

Special details

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1K.

Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.48622 (9)	0.15743 (6)	0.416803 (12)	0.0304
C2	0.3603 (4)	0.1099 (2)	0.38127 (5)	0.0281
C3	0.2838 (4)	−0.0364 (3)	0.37682 (6)	0.0346
C4	0.1900 (4)	−0.0764 (3)	0.34889 (6)	0.0393
C5	0.1767 (4)	0.0277 (3)	0.32499 (6)	0.0396
C6	0.2524 (4)	0.1741 (3)	0.32892 (5)	0.0341
C7	0.3456 (4)	0.2158 (2)	0.35687 (5)	0.0276
N8	0.4237 (3)	0.3662 (2)	0.36097 (4)	0.0253
C9	0.5657 (3)	0.4309 (3)	0.33734 (5)	0.0276
C10	0.4450 (4)	0.5452 (3)	0.31781 (5)	0.0332
N11	0.5822 (3)	0.6363 (2)	0.29678 (4)	0.0337
C12	0.7080 (5)	0.7493 (3)	0.31383 (6)	0.0481
C13	0.4533 (5)	0.7108 (4)	0.27208 (6)	0.0563
C14	0.3762 (3)	0.4539 (2)	0.38598 (5)	0.0234
O15	0.4559 (2)	0.57880 (16)	0.39037 (3)	0.0283
C16	0.2076 (3)	0.3910 (2)	0.40798 (4)	0.0235
O17	0.0944 (2)	0.51510 (16)	0.42200 (3)	0.0262
C18	−0.0094 (3)	0.6025 (2)	0.40093 (5)	0.0260
O19	−0.0057 (3)	0.57586 (17)	0.37345 (3)	0.0304
C20	−0.1245 (4)	0.7306 (2)	0.41584 (6)	0.0319
C21	0.2958 (3)	0.2901 (2)	0.43394 (5)	0.0261
C22	0.4057 (3)	0.3708 (2)	0.46073 (5)	0.0245
C23	0.3056 (3)	0.3782 (2)	0.48979 (5)	0.0244
C24	0.4019 (3)	0.4500 (2)	0.51469 (5)	0.0240
C25	0.5970 (4)	0.5166 (2)	0.51106 (5)	0.0245
C26	0.7005 (3)	0.5077 (2)	0.48265 (5)	0.0248
C27	0.6027 (3)	0.4344 (2)	0.45783 (5)	0.0264
O28	0.6775 (2)	0.58701 (18)	0.53679 (3)	0.0293
C29	0.8593 (4)	0.6789 (3)	0.53296 (5)	0.0331
N30	−0.0230 (3)	0.4375 (3)	0.26675 (5)	0.0438
O31	−0.1894 (4)	0.4705 (4)	0.25294 (6)	0.0814
O32	−0.0229 (4)	0.4637 (3)	0.29506 (5)	0.0755
O33	0.1335 (5)	0.3915 (4)	0.25447 (7)	0.0942
H211	0.1761	0.2310	0.4422	0.0326*
H161	0.1071	0.3314	0.3957	0.0278*
H202	−0.1128	0.8201	0.4036	0.0489*
H201	−0.0676	0.7515	0.4360	0.0485*
H203	−0.2688	0.7064	0.4177	0.0481*
H91	0.6828	0.4780	0.3484	0.0340*
H92	0.6181	0.3499	0.3242	0.0343*
H101	0.3718	0.6155	0.3315	0.0419*
H102	0.3431	0.4928	0.3051	0.0424*
H121	0.7961	0.8043	0.2994	0.0734*
H123	0.7946	0.7004	0.3298	0.0728*
H122	0.6113	0.8188	0.3239	0.0741*
H131	0.5404	0.7701	0.2587	0.0849*
H132	0.3504	0.7762	0.2822	0.0856*
H133	0.3810	0.6337	0.2599	0.0847*
H31	0.2961	−0.1064	0.3930	0.0425*
H41	0.1338	−0.1744	0.3463	0.0483*
H51	0.1160	0.0009	0.3056	0.0471*
H61	0.2407	0.2435	0.3128	0.0418*
H231	0.1699	0.3325	0.4920	0.0285*
H241	0.3322	0.4535	0.5343	0.0290*
H291	0.8826	0.7315	0.5524	0.0489*
H293	0.9787	0.6182	0.5275	0.0491*
H292	0.8342	0.7517	0.5168	0.0492*
H261	0.8357	0.5481	0.4800	0.0293*
H271	0.6714	0.4278	0.4386	0.0325*
H111	0.6739	0.5738	0.2873	0.0518*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0338 (3)	0.0269 (2)	0.0306 (2)	0.0001 (2)	−0.0047 (2)	0.0043 (2)
C2	0.0292 (11)	0.0244 (10)	0.0308 (10)	−0.0051 (9)	−0.0003 (9)	0.0016 (8)
C3	0.0408 (14)	0.0255 (11)	0.0374 (12)	−0.0042 (10)	0.0028 (10)	0.0032 (9)
C4	0.0438 (14)	0.0283 (12)	0.0459 (13)	−0.0102 (11)	−0.0007 (11)	−0.0042 (10)
C5	0.0426 (15)	0.0385 (13)	0.0377 (12)	−0.0097 (11)	−0.0054 (11)	−0.0090 (10)
C6	0.0406 (14)	0.0326 (12)	0.0291 (11)	−0.0072 (10)	−0.0027 (9)	0.0017 (9)
C7	0.0300 (12)	0.0248 (10)	0.0280 (10)	−0.0047 (9)	0.0013 (9)	0.0013 (8)
N8	0.0274 (9)	0.0244 (8)	0.0243 (8)	−0.0059 (7)	0.0021 (7)	0.0033 (7)
C9	0.0250 (11)	0.0318 (11)	0.0261 (10)	−0.0048 (9)	0.0031 (8)	0.0047 (8)
C10	0.0289 (12)	0.0392 (12)	0.0317 (11)	−0.0059 (10)	0.0011 (9)	0.0115 (9)
N11	0.0324 (10)	0.0390 (10)	0.0296 (9)	−0.0081 (9)	0.0006 (8)	0.0107 (8)
C12	0.0537 (17)	0.0428 (15)	0.0479 (15)	−0.0214 (13)	−0.0097 (13)	0.0117 (12)
C13	0.060 (2)	0.0667 (18)	0.0421 (14)	−0.0164 (16)	−0.0138 (13)	0.0302 (14)
C14	0.0208 (10)	0.0258 (10)	0.0235 (9)	−0.0024 (8)	−0.0033 (8)	0.0068 (8)
O15	0.0288 (8)	0.0264 (7)	0.0298 (7)	−0.0088 (6)	−0.0015 (6)	0.0015 (6)
C16	0.0212 (10)	0.0254 (10)	0.0239 (9)	−0.0050 (8)	0.0003 (8)	0.0026 (8)
O17	0.0261 (7)	0.0288 (7)	0.0237 (7)	−0.0028 (6)	−0.0011 (6)	0.0027 (6)
C18	0.0178 (9)	0.0294 (10)	0.0307 (10)	−0.0080 (9)	−0.0012 (8)	0.0051 (8)
O19	0.0285 (8)	0.0363 (8)	0.0263 (7)	−0.0016 (7)	−0.0046 (6)	0.0026 (6)
C20	0.0283 (11)	0.0303 (11)	0.0370 (11)	−0.0036 (9)	−0.0003 (10)	0.0001 (10)
C21	0.0249 (10)	0.0274 (10)	0.0260 (10)	−0.0074 (9)	−0.0018 (8)	0.0056 (8)
C22	0.0252 (10)	0.0231 (10)	0.0252 (9)	−0.0013 (8)	−0.0011 (8)	0.0069 (8)
C23	0.0194 (10)	0.0242 (10)	0.0297 (10)	−0.0014 (8)	0.0008 (8)	0.0059 (8)
C24	0.0217 (10)	0.0253 (10)	0.0250 (9)	0.0014 (8)	0.0029 (8)	0.0037 (8)
C25	0.0278 (11)	0.0201 (9)	0.0257 (10)	0.0041 (8)	−0.0023 (8)	0.0034 (8)
C26	0.0191 (10)	0.0272 (10)	0.0282 (10)	−0.0037 (8)	0.0024 (8)	0.0047 (8)
C27	0.0244 (10)	0.0311 (11)	0.0238 (9)	−0.0049 (9)	0.0018 (8)	0.0048 (8)
O28	0.0277 (8)	0.0322 (8)	0.0280 (7)	−0.0050 (6)	−0.0014 (6)	−0.0019 (6)
C29	0.0328 (12)	0.0318 (12)	0.0346 (11)	−0.0069 (10)	−0.0039 (9)	−0.0007 (9)
N30	0.0283 (11)	0.0607 (14)	0.0424 (11)	−0.0010 (11)	−0.0009 (9)	−0.0088 (10)
O31	0.0785 (18)	0.100 (2)	0.0661 (15)	0.0124 (17)	−0.0266 (14)	−0.0233 (15)
O32	0.0463 (13)	0.129 (2)	0.0510 (12)	0.0218 (15)	0.0041 (10)	−0.0063 (13)
O33	0.0730 (18)	0.115 (2)	0.095 (2)	0.0024 (18)	0.0305 (16)	−0.0492 (18)

Geometric parameters (Å, º)

S1—C2	1.774 (2)	C14—C16	1.534 (3)
S1—C21	1.840 (2)	C16—O17	1.442 (2)
C2—C3	1.393 (3)	C16—C21	1.533 (3)
C2—C7	1.406 (3)	C16—H161	0.981
C3—C4	1.386 (4)	O17—C18	1.361 (2)
C3—H31	0.934	C18—O19	1.203 (2)
C4—C5	1.379 (4)	C18—C20	1.491 (3)
C4—H41	0.943	C20—H202	0.951
C5—C6	1.388 (3)	C20—H201	0.958
C5—H51	0.950	C20—H203	0.948
C6—C7	1.388 (3)	C21—C22	1.523 (3)
C6—H61	0.927	C21—H211	0.989
C7—N8	1.428 (3)	C22—C23	1.403 (3)
N8—C9	1.475 (3)	C22—C27	1.382 (3)
N8—C14	1.358 (3)	C23—C24	1.386 (3)
C9—C10	1.521 (3)	C23—H231	0.959
C9—H91	0.979	C24—C25	1.385 (3)
C9—H92	0.969	C24—H241	0.954
C10—N11	1.492 (3)	C25—C26	1.389 (3)
C10—H101	0.972	C25—O28	1.367 (2)
C10—H102	0.966	C26—C27	1.394 (3)
N11—C12	1.474 (3)	C26—H261	0.940
N11—C13	1.495 (3)	C27—H271	0.937
N11—H111	0.900	O28—C29	1.424 (3)
C12—H121	0.966	C29—H291	0.968
C12—H123	0.981	C29—H293	0.959
C12—H122	0.971	C29—H292	0.958
C13—H131	0.955	N30—O31	1.250 (3)
C13—H132	0.975	N30—O32	1.238 (3)
C13—H133	0.972	N30—O33	1.200 (3)
C14—O15	1.228 (2)
C2—S1—C21	101.27 (10)	N8—C14—C16	115.97 (17)
S1—C2—C3	119.67 (17)	O15—C14—C16	121.30 (19)
S1—C2—C7	120.97 (16)	C14—C16—O17	109.48 (16)
C3—C2—C7	119.3 (2)	C14—C16—C21	113.60 (17)
C2—C3—C4	120.3 (2)	O17—C16—C21	108.68 (16)
C2—C3—H31	118.7	C14—C16—H161	108.7
C4—C3—H31	120.9	O17—C16—H161	107.6
C3—C4—C5	120.1 (2)	C21—C16—H161	108.6
C3—C4—H41	119.9	C16—O17—C18	113.32 (15)
C5—C4—H41	120.0	O17—C18—O19	122.1 (2)
C4—C5—C6	120.4 (2)	O17—C18—C20	112.52 (17)
C4—C5—H51	120.9	O19—C18—C20	125.4 (2)
C6—C5—H51	118.7	C18—C20—H202	110.6
C5—C6—C7	120.0 (2)	C18—C20—H201	110.4
C5—C6—H61	119.7	H202—C20—H201	108.1
C7—C6—H61	120.3	C18—C20—H203	110.1
C2—C7—C6	119.8 (2)	H202—C20—H203	108.0
C2—C7—N8	120.07 (19)	H201—C20—H203	109.5
C6—C7—N8	120.13 (19)	C16—C21—S1	108.67 (14)
C7—N8—C9	119.24 (17)	C16—C21—C22	116.55 (17)
C7—N8—C14	123.26 (17)	S1—C21—C22	107.18 (15)
C9—N8—C14	117.49 (17)	C16—C21—H211	106.4
N8—C9—C10	108.98 (17)	S1—C21—H211	108.5
N8—C9—H91	107.3	C22—C21—H211	109.3
C10—C9—H91	111.9	C21—C22—C23	118.97 (18)
N8—C9—H92	109.1	C21—C22—C27	122.67 (19)
C10—C9—H92	110.0	C23—C22—C27	118.34 (19)
H91—C9—H92	109.5	C22—C23—C24	120.41 (19)
C9—C10—N11	113.19 (18)	C22—C23—H231	118.6
C9—C10—H101	109.5	C24—C23—H231	121.0
N11—C10—H101	107.7	C23—C24—C25	120.32 (19)
C9—C10—H102	109.5	C23—C24—H241	119.4
N11—C10—H102	108.1	C25—C24—H241	120.3
H101—C10—H102	108.8	C24—C25—C26	120.12 (19)
C10—N11—C12	112.47 (19)	C24—C25—O28	116.06 (18)
C10—N11—C13	110.10 (18)	C26—C25—O28	123.8 (2)
C12—N11—C13	110.8 (2)	C25—C26—C27	119.0 (2)
C10—N11—H111	109.0	C25—C26—H261	121.3
C12—N11—H111	106.5	C27—C26—H261	119.7
C13—N11—H111	107.9	C26—C27—C22	121.75 (19)
N11—C12—H121	109.7	C26—C27—H271	119.6
N11—C12—H123	110.9	C22—C27—H271	118.6
H121—C12—H123	110.0	C25—O28—C29	118.11 (17)
N11—C12—H122	107.6	O28—C29—H291	107.3
H121—C12—H122	109.7	O28—C29—H293	110.9
H123—C12—H122	108.8	H291—C29—H293	110.8
N11—C13—H131	110.3	O28—C29—H292	109.2
N11—C13—H132	108.3	H291—C29—H292	109.3
H131—C13—H132	109.6	H293—C29—H292	109.4
N11—C13—H133	109.5	O31—N30—O32	115.0 (2)
H131—C13—H133	109.7	O31—N30—O33	125.2 (3)
H132—C13—H133	109.5	O32—N30—O33	119.6 (3)
N8—C14—O15	122.67 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C20—H201···O28^i	0.96	2.42	3.230 (3)	143
C20—H203···O15^ii	0.95	2.39	3.186 (3)	141
C9—H91···O19^iii	0.98	2.42	3.392 (3)	174
C10—H102···O32	0.97	2.39	3.221 (3)	144
C12—H121···O33^iv	0.97	2.48	3.346 (3)	149
C12—H123···O19^iii	0.98	2.52	3.496 (3)	176
C13—H131···O33^iv	0.95	2.41	3.283 (3)	153
C5—H51···O31^v	0.95	2.57	3.386 (3)	144
N11—H111···N30^iii	0.90	2.44	3.327 (3)	168
N11—H111···O31^iii	0.90	1.94	2.793 (3)	157
N11—H111···O32^iii	0.90	2.19	2.943 (3)	141

Symmetry codes: (i) x−1/2, −y+3/2, −z+1; (ii) x−1, y, z; (iii) x+1, y, z; (iv) −x+1, y+1/2, −z+1/2; (v) −x, y−1/2, −z+1/2.

(Diltiazemphosphatesesquihydrate)

Crystal data

2(C22H27N2O4S)·2(H2O4P)·3(H2O)	Z = 2
Mr = 1079.05	F(000) = 1140
Triclinic, P1	Dx = 1.381 Mg m^−3
a = 8.7929 (1) Å	Cu Kα radiation, λ = 1.54180 Å
b = 12.6645 (1) Å	Cell parameters from 109761 reflections
c = 23.7867 (2) Å	θ = 4–79°
α = 82.3345 (7)°	µ = 2.17 mm^−1
β = 81.4117 (7)°	T = 160 K
γ = 89.9824 (7)°	Lath, colorless
V = 2595.21 (4) Å^3	0.17 × 0.07 × 0.02 mm

Data collection

Oxford Diffraction SuperNova diffractometer	18568 reflections with I > 2.0σ(I)
Graphite monochromator	Rint = 0.066
ω scans	θmax = 72.1°, θmin = 3.5°
Absorption correction: multi-scan CrysAlisPro, (Agilent, 2011)	h = −10→10
Tmin = 0.62, Tmax = 0.96	k = −15→15
264132 measured reflections	l = −29→29
19821 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: difference Fourier map
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.049	Method = Modified Sheldrick w = 1/[σ^2(F^2) + ( 0.09P)^2 + 1.4P] , where P = (max(Fo^2,0) + 2Fc^2)/3
wR(F^2) = 0.128	(Δ/σ)max = 0.001
S = 1.00	Δρmax = 1.49 e Å^−3
19783 reflections	Δρmin = −0.46 e Å^−3
1376 parameters	Absolute structure: Flack (1983), 9652 Friedel-pairs
66 restraints	Absolute structure parameter: 0.020 (11)
Primary atom site location: Other

Special details

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1K.

Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.49980 (10)	0.49990 (8)	0.49983 (4)	0.0335
C2	0.4695 (4)	0.5780 (3)	0.43488 (13)	0.0298
C3	0.3219 (4)	0.6122 (3)	0.42825 (16)	0.0366
C4	0.2944 (4)	0.6692 (3)	0.37685 (16)	0.0405
C5	0.4141 (5)	0.6922 (3)	0.33212 (16)	0.0430
C6	0.5620 (4)	0.6596 (3)	0.33822 (14)	0.0389
C7	0.5901 (4)	0.6012 (3)	0.38948 (13)	0.0299
N8	0.7419 (3)	0.5642 (2)	0.39478 (10)	0.0284
C9	0.8195 (4)	0.5022 (3)	0.35076 (13)	0.0282
C10	0.9399 (4)	0.5719 (3)	0.31008 (14)	0.0327
N11	1.0375 (3)	0.5082 (2)	0.27060 (11)	0.0288
C12	1.1492 (4)	0.4417 (3)	0.29985 (15)	0.0385
C13	1.1160 (5)	0.5789 (3)	0.21937 (15)	0.0452
C14	0.8136 (4)	0.5761 (2)	0.44022 (12)	0.0270
O15	0.9372 (3)	0.53625 (19)	0.44662 (9)	0.0312
C16	0.7350 (4)	0.6492 (3)	0.48176 (13)	0.0264
O17	0.8502 (3)	0.69849 (18)	0.50760 (9)	0.0297
C18	0.9524 (4)	0.7624 (3)	0.46931 (14)	0.0312
O19	0.9422 (3)	0.7761 (2)	0.41857 (10)	0.0370
C20	1.0742 (4)	0.8102 (3)	0.49525 (16)	0.0370
C21	0.6172 (4)	0.5912 (3)	0.53066 (13)	0.0299
C22	0.6825 (4)	0.5279 (3)	0.57968 (12)	0.0270
C23	0.7528 (4)	0.4317 (3)	0.57471 (13)	0.0299
C24	0.8115 (4)	0.3732 (3)	0.62055 (13)	0.0268
C25	0.7985 (3)	0.4129 (3)	0.67268 (12)	0.0238
C26	0.7256 (3)	0.5095 (3)	0.67884 (13)	0.0258
C27	0.6682 (4)	0.5660 (3)	0.63299 (13)	0.0279
O28	0.8527 (3)	0.36327 (19)	0.72006 (9)	0.0311
C29	0.9507 (4)	0.2737 (3)	0.71292 (15)	0.0349
S31	0.51570 (10)	0.01691 (8)	0.49890 (4)	0.0333
H31	0.2428	0.5974	0.4585	0.0448*
C32	0.4951 (4)	0.0977 (3)	0.43376 (13)	0.0297
C33	0.3519 (4)	0.1387 (3)	0.42525 (15)	0.0357
C34	0.3330 (4)	0.1986 (3)	0.37349 (16)	0.0381
C35	0.4569 (4)	0.2191 (3)	0.32994 (15)	0.0404
C36	0.5996 (4)	0.1783 (3)	0.33793 (14)	0.0347
C37	0.6192 (4)	0.1181 (3)	0.38908 (13)	0.0282
N38	0.7674 (3)	0.0758 (2)	0.39640 (10)	0.0261
C39	0.8448 (4)	0.0119 (3)	0.35335 (12)	0.0265
C40	0.9846 (4)	0.0743 (3)	0.31856 (13)	0.0272
N41	1.0839 (3)	0.0063 (2)	0.28162 (10)	0.0238
H41	0.1958	0.6923	0.3717	0.0481*
C42	1.1884 (4)	0.0737 (3)	0.23586 (14)	0.0313
C43	1.1757 (4)	−0.0696 (3)	0.31507 (16)	0.0370
C44	0.8358 (4)	0.0855 (2)	0.44275 (12)	0.0252
O45	0.9556 (3)	0.04144 (18)	0.45129 (9)	0.0273
C46	0.7571 (3)	0.1601 (3)	0.48327 (12)	0.0254
O47	0.8721 (3)	0.20964 (18)	0.50916 (9)	0.0284
C48	0.9762 (4)	0.2725 (3)	0.47017 (14)	0.0286
O49	0.9688 (3)	0.28204 (19)	0.41945 (10)	0.0330
C50	1.0920 (4)	0.3242 (3)	0.49663 (16)	0.0370
C51	0.6356 (4)	0.1040 (3)	0.53149 (13)	0.0288
H51	0.3977	0.7305	0.2966	0.0512*
C52	0.6953 (4)	0.0364 (3)	0.58077 (13)	0.0259
C53	0.7597 (4)	−0.0619 (3)	0.57533 (13)	0.0289
C54	0.8120 (4)	−0.1244 (3)	0.62147 (13)	0.0289
C55	0.7982 (3)	−0.0861 (2)	0.67425 (12)	0.0231
C56	0.7290 (3)	0.0112 (3)	0.68077 (12)	0.0243
C57	0.6785 (3)	0.0717 (3)	0.63430 (13)	0.0259
O58	0.8458 (3)	−0.13943 (19)	0.72219 (9)	0.0300
C59	0.9404 (4)	−0.2308 (3)	0.71554 (14)	0.0346
S61	0.56384 (10)	0.68940 (8)	0.80859 (4)	0.0335
H61	0.6435	0.6774	0.3076	0.0467*
C62	0.5851 (4)	0.7379 (3)	0.87385 (13)	0.0303
C63	0.7268 (4)	0.7751 (3)	0.88228 (15)	0.0355
C64	0.7458 (4)	0.8094 (3)	0.93379 (16)	0.0388
C65	0.6221 (5)	0.8078 (3)	0.97703 (15)	0.0416
C66	0.4790 (4)	0.7714 (3)	0.96931 (14)	0.0352
C67	0.4587 (4)	0.7362 (3)	0.91831 (13)	0.0274
N68	0.3120 (3)	0.6979 (2)	0.91108 (10)	0.0257
C69	0.2343 (4)	0.6124 (3)	0.95382 (13)	0.0263
C70	0.0933 (4)	0.6574 (3)	0.98865 (13)	0.0278
N71	−0.0052 (3)	0.5704 (2)	1.02538 (10)	0.0246
C72	−0.1095 (4)	0.6149 (3)	1.07134 (14)	0.0317
C73	−0.0968 (4)	0.5117 (3)	0.99206 (16)	0.0380
C74	0.2436 (4)	0.7303 (2)	0.86420 (12)	0.0243
O75	0.1245 (3)	0.69089 (18)	0.85576 (9)	0.0269
C76	0.3226 (4)	0.8252 (3)	0.82381 (12)	0.0265
O77	0.2081 (3)	0.88790 (19)	0.79774 (9)	0.0298
C78	0.1035 (4)	0.9306 (3)	0.83677 (14)	0.0292
O79	0.1100 (3)	0.9154 (2)	0.88740 (10)	0.0334
C80	−0.0125 (4)	0.9965 (3)	0.80975 (16)	0.0381
C81	0.4446 (4)	0.7931 (3)	0.77574 (12)	0.0279
C82	0.3852 (4)	0.7494 (3)	0.72657 (13)	0.0263
C83	0.3196 (4)	0.6494 (3)	0.73214 (13)	0.0310
C84	0.2658 (4)	0.6107 (3)	0.68638 (13)	0.0277
C85	0.2801 (3)	0.6747 (3)	0.63348 (12)	0.0241
C86	0.3498 (3)	0.7748 (3)	0.62667 (12)	0.0240
C87	0.4025 (4)	0.8118 (3)	0.67277 (13)	0.0261
O88	0.2302 (3)	0.64499 (19)	0.58598 (9)	0.0311
C89	0.1310 (4)	0.5522 (3)	0.59371 (15)	0.0360
S91	0.57882 (10)	0.17322 (8)	0.80724 (4)	0.0335
H92	0.8663	0.4408	0.3698	0.0338*
C92	0.6101 (4)	0.2185 (3)	0.87220 (13)	0.0307
H91	0.7427	0.4783	0.3300	0.0339*
C93	0.7570 (4)	0.2496 (3)	0.87864 (15)	0.0364
C94	0.7837 (4)	0.2807 (3)	0.93031 (16)	0.0397
C95	0.6649 (5)	0.2812 (3)	0.97501 (16)	0.0425
C96	0.5173 (4)	0.2515 (3)	0.96875 (15)	0.0392
C97	0.4883 (4)	0.2194 (3)	0.91787 (13)	0.0292
N98	0.3373 (3)	0.1847 (2)	0.91256 (10)	0.0277
C99	0.2601 (4)	0.1010 (3)	0.95650 (13)	0.0289
C100	0.1378 (4)	0.1499 (3)	0.99720 (14)	0.0319
N101	0.0413 (3)	0.0664 (2)	1.03647 (11)	0.0284
H102	0.8917	0.6280	0.2873	0.0387*
C102	−0.0696 (4)	0.0147 (3)	1.00745 (16)	0.0392
H101	1.0050	0.6062	0.3313	0.0389*
C103	−0.0379 (5)	0.1117 (3)	1.08771 (15)	0.0438
C104	0.2655 (4)	0.2190 (3)	0.86705 (13)	0.0267
O105	0.1414 (3)	0.18280 (19)	0.86051 (10)	0.0307
C106	0.3430 (4)	0.3133 (3)	0.82545 (13)	0.0269
O107	0.2274 (3)	0.37559 (18)	0.79966 (9)	0.0298
C108	0.1266 (4)	0.4204 (3)	0.83847 (14)	0.0301
O109	0.1370 (3)	0.4084 (2)	0.88870 (10)	0.0356
C110	0.0041 (4)	0.4813 (3)	0.81227 (15)	0.0360
C111	0.4607 (4)	0.2797 (3)	0.77640 (13)	0.0286
H111	0.974 (2)	0.4636 (17)	0.2588 (9)	0.043 (2)*
C112	0.3959 (4)	0.2409 (3)	0.72739 (13)	0.0274
C113	0.3269 (4)	0.1415 (3)	0.73213 (13)	0.0294
C114	0.2700 (4)	0.1063 (3)	0.68610 (13)	0.0267
C115	0.2827 (3)	0.1726 (2)	0.63374 (12)	0.0228
C116	0.3526 (4)	0.2717 (3)	0.62799 (13)	0.0254
C117	0.4091 (3)	0.3059 (3)	0.67411 (13)	0.0263
O118	0.2302 (3)	0.14595 (19)	0.58626 (9)	0.0306
C119	0.1360 (4)	0.0515 (3)	0.59215 (14)	0.0336
P121	0.57908 (10)	0.74840 (7)	0.15508 (4)	0.0255
H122	1.0980	0.4026	0.3343	0.0573*
O122	0.7028 (3)	0.8273 (2)	0.11679 (11)	0.0404
H123	1.1980	0.3942	0.2748	0.0576*
O123	0.6775 (3)	0.6687 (2)	0.18990 (11)	0.0371
H121	1.2250	0.4876	0.3086	0.0584*
O124	0.4776 (3)	0.8105 (2)	0.19493 (11)	0.0379
O125	0.4924 (3)	0.6933 (2)	0.11721 (10)	0.0324
P126	0.49998 (10)	1.24910 (7)	0.15205 (4)	0.0250
O127	0.6010 (3)	1.3315 (2)	0.11205 (11)	0.0385
O128	0.5864 (3)	1.17454 (19)	0.19009 (10)	0.0316
O129	0.3768 (3)	1.3090 (2)	0.19039 (11)	0.0391
O130	0.4013 (3)	1.1870 (2)	0.11736 (11)	0.0347
P131	1.15434 (9)	0.83729 (7)	0.12313 (4)	0.0249
H133	1.0429	0.6233	0.2019	0.0678*
O132	1.2107 (3)	0.72581 (19)	0.10658 (10)	0.0292
H131	1.1714	0.5375	0.1919	0.0677*
O133	1.2047 (3)	0.8473 (2)	0.18246 (10)	0.0353
H132	1.1899	0.6233	0.2316	0.0674*
O134	1.2289 (3)	0.9241 (2)	0.07731 (11)	0.0362
O135	0.9819 (3)	0.8368 (2)	0.13180 (10)	0.0335
P136	0.92475 (9)	0.32205 (7)	0.18405 (4)	0.0249
O137	1.0973 (3)	0.3262 (2)	0.17521 (10)	0.0336
O138	0.8682 (3)	0.20264 (19)	0.20065 (10)	0.0296
O139	0.8495 (3)	0.3856 (2)	0.23003 (11)	0.0357
O140	0.8738 (3)	0.3621 (2)	0.12440 (10)	0.0351
O141	0.8803 (3)	0.8830 (2)	0.24438 (11)	0.0408
O142	1.1990 (3)	1.4289 (2)	0.06287 (11)	0.0412
O143	0.5719 (3)	0.4767 (2)	0.22903 (13)	0.0382
O144	0.5911 (3)	−0.0327 (2)	0.24859 (12)	0.0356
O145	0.5065 (3)	1.0144 (2)	0.07821 (13)	0.0372
O146	0.4879 (3)	0.5150 (2)	0.05834 (12)	0.0365
H161	0.6834	0.7045	0.4592	0.0318*
H203	1.0582	0.8839	0.4965	0.0570*
H201	1.0744	0.7775	0.5336	0.0567*
H202	1.1727	0.8046	0.4737	0.0558*
H211	0.5532	0.6462	0.5456	0.0364*
H231	0.7607	0.4044	0.5394	0.0353*
H241	0.8557	0.3075	0.6167	0.0315*
H261	0.7154	0.5355	0.7140	0.0310*
H271	0.6194	0.6301	0.6375	0.0340*
H293	0.9890	0.2539	0.7478	0.0518*
H291	1.0342	0.2939	0.6821	0.0514*
H292	0.8935	0.2168	0.7037	0.0525*
H331	0.2690	0.1243	0.4553	0.0436*
H341	0.2361	0.2263	0.3685	0.0459*
H351	0.4456	0.2598	0.2947	0.0486*
H361	0.6823	0.1911	0.3087	0.0414*
H391	0.8751	−0.0545	0.3717	0.0313*
H392	0.7711	−0.0035	0.3290	0.0319*
H401	0.9498	0.1323	0.2937	0.0325*
H402	1.0464	0.1010	0.3448	0.0330*
H411	1.021 (2)	−0.0294 (17)	0.2648 (9)	0.035 (2)*
H423	1.1239	0.1158	0.2119	0.0459*
H421	1.2519	0.0256	0.2140	0.0463*
H422	1.2547	0.1192	0.2523	0.0476*
H431	1.1092	−0.1130	0.3456	0.0557*
H433	1.2280	−0.1148	0.2895	0.0559*
H432	1.2505	−0.0298	0.3302	0.0567*
H461	0.7079	0.2156	0.4614	0.0306*
H501	1.0581	0.3916	0.5062	0.0566*
H503	1.1851	0.3338	0.4709	0.0563*
H502	1.1082	0.2805	0.5306	0.0567*
H511	0.5715	0.1617	0.5458	0.0341*
H531	0.7687	−0.0884	0.5402	0.0342*
H541	0.8526	−0.1911	0.6174	0.0348*
H561	0.7188	0.0363	0.7164	0.0288*
H571	0.6328	0.1366	0.6392	0.0310*
H591	0.8829	−0.2863	0.7036	0.0517*
H593	0.9699	−0.2553	0.7516	0.0513*
H592	1.0294	−0.2118	0.6876	0.0517*
H631	0.8095	0.7765	0.8532	0.0436*
H641	0.8432	0.8324	0.9383	0.0470*
H651	0.6336	0.8314	1.0120	0.0494*
H661	0.3966	0.7697	0.9984	0.0423*
H692	0.3078	0.5856	0.9783	0.0319*
H691	0.2054	0.5556	0.9349	0.0309*
H702	0.0330	0.6974	0.9614	0.0337*
H701	0.1288	0.7035	1.0135	0.0329*
H711	0.058 (2)	0.5266 (16)	1.0421 (9)	0.036 (2)*
H721	−0.0446	0.6492	1.0934	0.0473*
H723	−0.1816	0.6648	1.0554	0.0482*
H722	−0.1667	0.5561	1.0961	0.0477*
H732	−0.1486	0.4520	1.0176	0.0566*
H731	−0.0292	0.4849	0.9611	0.0566*
H733	−0.1727	0.5583	0.9776	0.0576*
H761	0.3727	0.8707	0.8455	0.0329*
H802	−0.1016	0.9969	0.8371	0.0570*
H801	−0.0368	0.9677	0.7773	0.0577*
H803	0.0260	1.0679	0.7980	0.0574*
H811	0.5076	0.8565	0.7612	0.0340*
H831	0.3122	0.6051	0.7672	0.0364*
H841	0.2223	0.5429	0.6912	0.0328*
H861	0.3626	0.8168	0.5910	0.0298*
H871	0.4492	0.8793	0.6675	0.0309*
H892	0.0968	0.5467	0.5582	0.0536*
H891	0.0440	0.5593	0.6226	0.0538*
H893	0.1869	0.4898	0.6051	0.0544*
H931	0.8378	0.2505	0.8479	0.0446*
H941	0.8819	0.3022	0.9358	0.0475*
H951	0.6824	0.3027	1.0104	0.0503*
H961	0.4367	0.2528	0.9999	0.0465*
H991	0.3385	0.0668	0.9772	0.0348*
H992	0.2120	0.0485	0.9382	0.0348*
H1001	0.0702	0.1933	0.9759	0.0382*
H1002	0.1859	0.1959	1.0198	0.0375*
H1011	0.105 (2)	0.0168 (16)	1.0485 (9)	0.043 (2)*
H1022	−0.1200	−0.0443	1.0325	0.0584*
H1021	−0.1451	0.0656	0.9985	0.0594*
H1023	−0.0180	−0.0090	0.9732	0.0587*
H1032	−0.1002	0.0588	1.1131	0.0659*
H1033	−0.1030	0.1678	1.0753	0.0653*
H1031	0.0363	0.1401	1.1073	0.0659*
H1061	0.3954	0.3580	0.8475	0.0318*
H1102	−0.0044	0.4593	0.7767	0.0544*
H1103	−0.0935	0.4738	0.8355	0.0538*
H1101	0.0310	0.5545	0.8050	0.0552*
H1111	0.5244	0.3430	0.7613	0.0337*
H1131	0.3194	0.0963	0.7671	0.0349*
H1141	0.2268	0.0394	0.6892	0.0318*
H1161	0.3619	0.3159	0.5928	0.0307*
H1171	0.4569	0.3725	0.6695	0.0322*
H1192	0.1956	−0.0090	0.6011	0.0509*
H1193	0.0998	0.0472	0.5574	0.0506*
H1191	0.0523	0.0532	0.6227	0.0505*
H1221	0.796 (3)	0.828 (4)	0.122 (2)	0.060 (2)*
H1231	0.627 (5)	0.613 (2)	0.201 (2)	0.056 (2)*
H1291	0.287 (3)	1.312 (4)	0.183 (2)	0.059 (2)*
H1301	0.452 (5)	1.139 (3)	0.1040 (19)	0.053 (2)*
H1321	1.305 (2)	0.714 (4)	0.1081 (18)	0.044 (2)*
H1331	1.293 (3)	0.820 (4)	0.187 (2)	0.053 (2)*
H1381	0.776 (2)	0.192 (4)	0.1981 (18)	0.044 (2)*
H1401	0.780 (3)	0.342 (4)	0.121 (2)	0.053 (2)*
H1412	0.790 (3)	0.900 (4)	0.2454 (17)	0.062 (2)*
H1411	0.904 (5)	0.856 (4)	0.2112 (13)	0.061 (2)*
H1422	1.172 (5)	1.391 (4)	0.0971 (12)	0.062 (2)*
H1421	1.290 (3)	1.445 (4)	0.0616 (17)	0.062 (2)*
H1432	0.645 (4)	0.445 (4)	0.238 (2)	0.057 (2)*
H1431	0.519 (5)	0.446 (4)	0.211 (2)	0.057 (2)*
H1442	0.589 (6)	0.020 (3)	0.2244 (17)	0.054 (2)*
H1441	0.559 (6)	−0.070 (3)	0.2285 (18)	0.054 (2)*
H1452	0.441 (4)	0.993 (4)	0.062 (2)	0.056 (2)*
H1451	0.565 (5)	0.973 (3)	0.0928 (19)	0.056 (2)*
H1462	0.492 (6)	0.560 (3)	0.0800 (18)	0.055 (2)*
H1461	0.525 (6)	0.478 (4)	0.0817 (17)	0.055 (2)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0310 (4)	0.0384 (5)	0.0281 (4)	0.0009 (4)	−0.0019 (3)	0.0033 (3)
C2	0.0313 (17)	0.0310 (17)	0.0262 (15)	0.0049 (14)	−0.0036 (12)	−0.0022 (12)
C3	0.0273 (17)	0.042 (2)	0.0406 (18)	0.0082 (15)	−0.0030 (14)	−0.0078 (15)
C4	0.0356 (18)	0.045 (2)	0.0441 (19)	0.0173 (17)	−0.0112 (15)	−0.0118 (16)
C5	0.048 (2)	0.049 (2)	0.0339 (18)	0.0208 (19)	−0.0132 (15)	−0.0046 (16)
C6	0.0408 (19)	0.047 (2)	0.0269 (16)	0.0140 (17)	−0.0023 (14)	−0.0020 (14)
C7	0.0312 (16)	0.0354 (18)	0.0227 (14)	0.0131 (14)	−0.0014 (12)	−0.0054 (12)
N8	0.0294 (14)	0.0317 (15)	0.0218 (12)	0.0115 (12)	0.0020 (10)	−0.0024 (10)
C9	0.0299 (16)	0.0269 (16)	0.0267 (14)	0.0063 (13)	0.0016 (12)	−0.0064 (12)
C10	0.0387 (18)	0.0271 (17)	0.0289 (16)	0.0070 (15)	0.0061 (13)	−0.0040 (13)
N11	0.0352 (14)	0.0225 (13)	0.0256 (13)	−0.0001 (12)	0.0048 (11)	−0.0030 (10)
C12	0.0330 (18)	0.043 (2)	0.0380 (18)	0.0087 (16)	0.0001 (14)	−0.0083 (15)
C13	0.058 (2)	0.038 (2)	0.0319 (18)	−0.0097 (18)	0.0141 (17)	0.0009 (15)
C14	0.0331 (16)	0.0226 (15)	0.0218 (14)	0.0038 (13)	0.0024 (12)	0.0020 (11)
O15	0.0303 (12)	0.0294 (12)	0.0313 (11)	0.0108 (10)	0.0003 (9)	0.0000 (9)
C16	0.0282 (15)	0.0264 (16)	0.0238 (14)	0.0085 (13)	−0.0012 (11)	−0.0030 (12)
O17	0.0340 (12)	0.0264 (12)	0.0261 (10)	0.0031 (10)	0.0000 (9)	0.0007 (9)
C18	0.0339 (17)	0.0249 (16)	0.0322 (17)	0.0099 (14)	0.0002 (13)	−0.0005 (13)
O19	0.0444 (14)	0.0339 (13)	0.0285 (12)	0.0032 (11)	0.0006 (10)	0.0035 (10)
C20	0.0378 (19)	0.0311 (18)	0.0405 (18)	0.0051 (15)	−0.0040 (15)	−0.0005 (14)
C21	0.0313 (16)	0.0290 (17)	0.0260 (15)	0.0070 (14)	0.0032 (12)	0.0003 (12)
C22	0.0255 (15)	0.0304 (17)	0.0215 (14)	0.0022 (13)	0.0034 (11)	0.0017 (12)
C23	0.0322 (17)	0.0321 (18)	0.0229 (14)	0.0039 (14)	0.0029 (12)	−0.0032 (12)
C24	0.0274 (15)	0.0256 (16)	0.0260 (14)	0.0036 (13)	0.0000 (12)	−0.0026 (12)
C25	0.0184 (13)	0.0280 (16)	0.0231 (14)	−0.0034 (12)	−0.0007 (11)	0.0015 (11)
C26	0.0224 (15)	0.0283 (16)	0.0260 (14)	−0.0027 (13)	0.0013 (11)	−0.0061 (12)
C27	0.0232 (15)	0.0271 (16)	0.0319 (15)	0.0052 (13)	0.0018 (12)	−0.0049 (12)
O28	0.0347 (12)	0.0327 (13)	0.0269 (11)	0.0085 (10)	−0.0075 (9)	−0.0050 (9)
C29	0.0376 (18)	0.0312 (18)	0.0358 (17)	0.0100 (15)	−0.0082 (14)	−0.0011 (14)
S31	0.0281 (4)	0.0412 (5)	0.0275 (4)	0.0013 (4)	−0.0004 (3)	0.0023 (3)
C32	0.0247 (15)	0.0351 (18)	0.0282 (15)	0.0060 (14)	−0.0025 (12)	−0.0021 (13)
C33	0.0268 (16)	0.046 (2)	0.0344 (17)	0.0096 (15)	−0.0031 (13)	−0.0093 (15)
C34	0.0268 (17)	0.047 (2)	0.0422 (19)	0.0137 (16)	−0.0088 (14)	−0.0095 (16)
C35	0.0404 (19)	0.051 (2)	0.0307 (17)	0.0159 (18)	−0.0094 (14)	−0.0028 (15)
C36	0.0324 (17)	0.043 (2)	0.0270 (15)	0.0094 (15)	−0.0009 (13)	−0.0035 (14)
C37	0.0268 (16)	0.0337 (17)	0.0234 (14)	0.0103 (14)	−0.0012 (11)	−0.0046 (12)
N38	0.0237 (12)	0.0345 (15)	0.0189 (12)	0.0121 (11)	0.0016 (9)	−0.0046 (10)
C39	0.0248 (15)	0.0307 (17)	0.0224 (14)	0.0063 (13)	0.0039 (11)	−0.0061 (12)
C40	0.0294 (16)	0.0257 (16)	0.0240 (14)	0.0057 (13)	0.0044 (12)	−0.0042 (12)
N41	0.0224 (12)	0.0229 (13)	0.0242 (12)	0.0036 (10)	0.0029 (9)	−0.0033 (10)
C42	0.0287 (16)	0.0297 (17)	0.0313 (16)	0.0036 (14)	0.0072 (12)	−0.0016 (13)
C43	0.0299 (16)	0.0345 (19)	0.0414 (18)	0.0086 (15)	0.0014 (14)	0.0064 (14)
C44	0.0293 (16)	0.0236 (15)	0.0197 (13)	0.0036 (13)	0.0032 (11)	−0.0001 (11)
O45	0.0270 (11)	0.0275 (11)	0.0260 (10)	0.0095 (9)	−0.0013 (8)	−0.0021 (8)
C46	0.0262 (15)	0.0275 (16)	0.0215 (13)	0.0084 (13)	−0.0009 (11)	−0.0031 (11)
O47	0.0329 (12)	0.0286 (12)	0.0230 (10)	0.0060 (10)	−0.0029 (8)	−0.0024 (9)
C48	0.0301 (16)	0.0218 (15)	0.0324 (16)	0.0113 (13)	−0.0030 (12)	0.0000 (12)
O49	0.0403 (13)	0.0300 (12)	0.0260 (11)	0.0041 (10)	−0.0009 (9)	0.0017 (9)
C50	0.0363 (18)	0.0329 (19)	0.0419 (19)	0.0055 (15)	−0.0082 (15)	−0.0028 (14)
C51	0.0303 (16)	0.0311 (17)	0.0233 (14)	0.0082 (14)	0.0019 (12)	−0.0042 (12)
C52	0.0228 (15)	0.0289 (16)	0.0230 (14)	0.0025 (12)	0.0041 (11)	−0.0011 (12)
C53	0.0334 (17)	0.0311 (17)	0.0205 (14)	0.0045 (14)	0.0024 (12)	−0.0048 (12)
C54	0.0308 (16)	0.0287 (17)	0.0258 (15)	0.0085 (14)	0.0004 (12)	−0.0036 (12)
C55	0.0200 (14)	0.0253 (15)	0.0221 (13)	−0.0035 (12)	−0.0001 (11)	0.0004 (11)
C56	0.0228 (15)	0.0263 (16)	0.0231 (14)	−0.0005 (12)	0.0015 (11)	−0.0065 (11)
C57	0.0220 (14)	0.0242 (16)	0.0297 (15)	0.0025 (12)	0.0026 (11)	−0.0046 (12)
O58	0.0353 (12)	0.0313 (12)	0.0241 (10)	0.0078 (10)	−0.0069 (9)	−0.0038 (9)
C59	0.0379 (18)	0.0318 (18)	0.0326 (17)	0.0094 (15)	−0.0039 (14)	−0.0006 (13)
S61	0.0295 (4)	0.0440 (5)	0.0273 (4)	−0.0006 (4)	−0.0008 (3)	−0.0093 (3)
C62	0.0278 (16)	0.0350 (18)	0.0269 (15)	−0.0065 (14)	−0.0014 (12)	−0.0029 (13)
C63	0.0273 (16)	0.040 (2)	0.0376 (18)	−0.0055 (15)	−0.0019 (13)	−0.0009 (14)
C64	0.0278 (17)	0.048 (2)	0.0406 (19)	−0.0120 (16)	−0.0080 (14)	−0.0030 (16)
C65	0.044 (2)	0.055 (2)	0.0276 (16)	−0.0156 (18)	−0.0101 (14)	−0.0070 (15)
C66	0.0308 (17)	0.044 (2)	0.0290 (16)	−0.0090 (15)	0.0002 (13)	−0.0028 (14)
C67	0.0282 (16)	0.0300 (17)	0.0224 (14)	−0.0089 (13)	−0.0020 (11)	−0.0001 (12)
N68	0.0232 (12)	0.0324 (15)	0.0197 (12)	−0.0095 (11)	−0.0002 (9)	−0.0007 (10)
C69	0.0239 (15)	0.0276 (16)	0.0250 (14)	−0.0054 (13)	0.0022 (11)	−0.0015 (12)
C70	0.0266 (15)	0.0285 (17)	0.0261 (14)	−0.0063 (13)	0.0035 (12)	−0.0039 (12)
N71	0.0237 (12)	0.0241 (13)	0.0244 (12)	−0.0035 (11)	0.0029 (10)	−0.0043 (10)
C72	0.0295 (16)	0.0342 (18)	0.0294 (16)	−0.0024 (14)	0.0060 (12)	−0.0087 (13)
C73	0.0325 (17)	0.043 (2)	0.0390 (18)	−0.0069 (16)	0.0014 (14)	−0.0163 (15)
C74	0.0288 (16)	0.0241 (15)	0.0192 (13)	−0.0055 (13)	0.0022 (11)	−0.0069 (11)
O75	0.0275 (11)	0.0269 (12)	0.0262 (10)	−0.0078 (9)	−0.0016 (8)	−0.0053 (8)
C76	0.0293 (16)	0.0278 (16)	0.0215 (14)	−0.0068 (13)	−0.0015 (11)	−0.0028 (12)
O77	0.0347 (12)	0.0286 (12)	0.0254 (10)	−0.0044 (10)	−0.0018 (9)	−0.0042 (9)
C78	0.0310 (16)	0.0250 (16)	0.0318 (17)	−0.0084 (13)	−0.0015 (13)	−0.0082 (13)
O79	0.0406 (14)	0.0345 (13)	0.0249 (11)	−0.0025 (11)	−0.0005 (9)	−0.0079 (9)
C80	0.0358 (19)	0.039 (2)	0.0411 (19)	−0.0015 (16)	−0.0101 (15)	−0.0067 (15)
C81	0.0322 (16)	0.0294 (16)	0.0201 (13)	−0.0056 (13)	0.0010 (12)	−0.0017 (12)
C82	0.0223 (15)	0.0335 (17)	0.0224 (14)	−0.0033 (13)	0.0010 (11)	−0.0057 (12)
C83	0.0333 (17)	0.0365 (19)	0.0205 (14)	−0.0048 (14)	0.0032 (12)	−0.0016 (12)
C84	0.0327 (16)	0.0237 (16)	0.0259 (14)	−0.0044 (13)	−0.0003 (12)	−0.0046 (12)
C85	0.0218 (14)	0.0312 (17)	0.0201 (13)	0.0043 (12)	−0.0021 (11)	−0.0075 (11)
C86	0.0232 (14)	0.0260 (16)	0.0209 (13)	0.0004 (12)	0.0005 (11)	−0.0005 (11)
C87	0.0238 (14)	0.0246 (16)	0.0278 (15)	−0.0036 (12)	0.0025 (11)	−0.0029 (12)
O88	0.0347 (12)	0.0345 (13)	0.0245 (10)	−0.0060 (10)	−0.0058 (9)	−0.0034 (9)
C89	0.0384 (19)	0.039 (2)	0.0322 (17)	−0.0078 (16)	−0.0043 (14)	−0.0109 (14)
S91	0.0315 (4)	0.0417 (5)	0.0279 (4)	0.0014 (4)	−0.0019 (3)	−0.0096 (3)
C92	0.0306 (16)	0.0356 (18)	0.0254 (15)	−0.0038 (14)	−0.0029 (12)	−0.0038 (13)
C93	0.0321 (17)	0.040 (2)	0.0349 (17)	−0.0060 (15)	−0.0021 (14)	−0.0014 (15)
C94	0.0363 (19)	0.042 (2)	0.0417 (19)	−0.0148 (16)	−0.0124 (15)	0.0000 (16)
C95	0.046 (2)	0.047 (2)	0.0364 (18)	−0.0137 (18)	−0.0133 (15)	−0.0049 (16)
C96	0.041 (2)	0.047 (2)	0.0282 (16)	−0.0151 (17)	−0.0016 (14)	−0.0072 (15)
C97	0.0302 (16)	0.0314 (17)	0.0252 (15)	−0.0098 (13)	−0.0041 (12)	−0.0016 (12)
N98	0.0305 (14)	0.0293 (15)	0.0212 (12)	−0.0110 (11)	0.0020 (10)	−0.0024 (10)
C99	0.0317 (16)	0.0257 (16)	0.0267 (15)	−0.0069 (13)	0.0017 (12)	−0.0013 (12)
C100	0.0384 (18)	0.0258 (17)	0.0286 (15)	−0.0060 (14)	0.0056 (13)	−0.0047 (13)
N101	0.0330 (14)	0.0241 (13)	0.0249 (12)	−0.0006 (11)	0.0049 (10)	−0.0023 (10)
C102	0.0314 (18)	0.043 (2)	0.0401 (19)	−0.0038 (16)	0.0022 (14)	−0.0017 (16)
C103	0.056 (2)	0.037 (2)	0.0329 (18)	0.0028 (18)	0.0154 (16)	−0.0100 (15)
C104	0.0302 (17)	0.0274 (16)	0.0227 (14)	−0.0049 (13)	0.0003 (12)	−0.0085 (12)
O105	0.0311 (12)	0.0303 (12)	0.0304 (11)	−0.0085 (10)	−0.0017 (9)	−0.0062 (9)
C106	0.0285 (15)	0.0266 (16)	0.0248 (14)	−0.0060 (13)	−0.0002 (12)	−0.0053 (12)
O107	0.0333 (12)	0.0295 (12)	0.0258 (11)	−0.0018 (10)	−0.0007 (9)	−0.0054 (9)
C108	0.0309 (17)	0.0254 (17)	0.0333 (17)	−0.0101 (14)	0.0016 (13)	−0.0091 (13)
O109	0.0424 (14)	0.0355 (13)	0.0293 (12)	−0.0001 (11)	−0.0008 (10)	−0.0109 (10)
C110	0.0356 (18)	0.0332 (19)	0.0401 (18)	−0.0025 (15)	−0.0044 (14)	−0.0093 (15)
C111	0.0284 (16)	0.0307 (17)	0.0247 (14)	−0.0054 (13)	0.0031 (12)	−0.0040 (12)
C112	0.0259 (15)	0.0327 (17)	0.0224 (14)	−0.0015 (13)	0.0029 (11)	−0.0069 (12)
C113	0.0319 (17)	0.0326 (18)	0.0208 (14)	−0.0044 (14)	0.0036 (12)	−0.0012 (12)
C114	0.0280 (15)	0.0239 (15)	0.0267 (14)	−0.0042 (13)	0.0009 (12)	−0.0036 (12)
C115	0.0181 (13)	0.0268 (16)	0.0233 (13)	0.0031 (12)	−0.0004 (10)	−0.0058 (11)
C116	0.0235 (15)	0.0257 (16)	0.0241 (14)	0.0012 (12)	0.0008 (11)	0.0021 (11)
C117	0.0234 (14)	0.0228 (15)	0.0296 (15)	−0.0042 (12)	0.0036 (11)	−0.0013 (12)
O118	0.0350 (12)	0.0320 (13)	0.0248 (10)	−0.0053 (10)	−0.0065 (9)	−0.0013 (9)
C119	0.0377 (18)	0.0340 (18)	0.0305 (16)	−0.0048 (15)	−0.0053 (13)	−0.0088 (13)
P121	0.0226 (4)	0.0249 (4)	0.0299 (4)	0.0009 (3)	−0.0059 (3)	−0.0047 (3)
O122	0.0252 (12)	0.0476 (16)	0.0461 (14)	−0.0067 (11)	−0.0116 (11)	0.0091 (12)
O123	0.0331 (13)	0.0343 (14)	0.0436 (13)	−0.0002 (11)	−0.0120 (10)	0.0028 (11)
O124	0.0296 (12)	0.0452 (15)	0.0452 (14)	0.0080 (11)	−0.0118 (10)	−0.0218 (11)
O125	0.0263 (11)	0.0355 (13)	0.0387 (12)	0.0034 (10)	−0.0078 (9)	−0.0136 (10)
P126	0.0215 (4)	0.0241 (4)	0.0300 (4)	0.0011 (3)	−0.0056 (3)	−0.0039 (3)
O127	0.0326 (12)	0.0374 (14)	0.0443 (14)	−0.0021 (11)	−0.0133 (10)	0.0079 (11)
O128	0.0247 (11)	0.0293 (12)	0.0398 (12)	−0.0008 (9)	−0.0076 (9)	0.0019 (10)
O129	0.0252 (12)	0.0513 (16)	0.0464 (14)	0.0106 (12)	−0.0106 (10)	−0.0214 (12)
O130	0.0307 (12)	0.0368 (14)	0.0412 (13)	0.0057 (11)	−0.0134 (10)	−0.0136 (10)
P131	0.0168 (3)	0.0268 (4)	0.0312 (4)	−0.0004 (3)	−0.0027 (3)	−0.0053 (3)
O132	0.0221 (10)	0.0306 (12)	0.0372 (12)	−0.0005 (9)	−0.0061 (9)	−0.0111 (9)
O133	0.0268 (12)	0.0453 (15)	0.0373 (12)	0.0074 (11)	−0.0055 (9)	−0.0171 (11)
O134	0.0247 (11)	0.0309 (13)	0.0499 (14)	−0.0036 (10)	−0.0026 (10)	0.0019 (10)
O135	0.0200 (11)	0.0376 (14)	0.0435 (13)	−0.0010 (10)	−0.0029 (9)	−0.0090 (10)
P136	0.0167 (3)	0.0267 (4)	0.0313 (4)	0.0027 (3)	−0.0034 (3)	−0.0034 (3)
O137	0.0183 (11)	0.0380 (14)	0.0422 (13)	0.0020 (10)	−0.0013 (9)	−0.0016 (10)
O138	0.0222 (10)	0.0309 (12)	0.0342 (11)	0.0035 (10)	−0.0051 (9)	0.0017 (9)
O139	0.0237 (11)	0.0346 (13)	0.0503 (14)	0.0052 (10)	−0.0025 (10)	−0.0146 (11)
O140	0.0265 (11)	0.0387 (14)	0.0366 (12)	−0.0037 (10)	−0.0060 (9)	0.0089 (10)
O141	0.0256 (12)	0.0546 (17)	0.0449 (14)	0.0021 (12)	−0.0001 (10)	−0.0227 (12)
O142	0.0256 (12)	0.0474 (16)	0.0443 (14)	−0.0009 (11)	0.0007 (10)	0.0107 (12)
O143	0.0293 (13)	0.0278 (13)	0.0592 (16)	0.0069 (11)	−0.0071 (11)	−0.0119 (11)
O144	0.0352 (13)	0.0260 (13)	0.0479 (14)	−0.0015 (11)	−0.0107 (11)	−0.0078 (10)
O145	0.0288 (12)	0.0239 (12)	0.0595 (16)	−0.0019 (10)	−0.0084 (11)	−0.0062 (11)
O146	0.0356 (13)	0.0285 (13)	0.0477 (14)	0.0054 (11)	−0.0114 (11)	−0.0069 (10)

Geometric parameters (Å, º)

S1—C2	1.776 (3)	C70—N71	1.498 (4)
S1—C21	1.842 (4)	C70—H702	0.986
C2—C3	1.392 (4)	C70—H701	0.967
C2—C7	1.397 (4)	N71—C72	1.490 (4)
C3—C4	1.389 (5)	N71—C73	1.476 (5)
C3—H31	0.922	N71—H711	0.887 (18)
C4—C5	1.381 (6)	C72—H721	0.969
C4—H41	0.935	C72—H723	0.976
C5—C6	1.387 (5)	C72—H722	0.975
C5—H51	0.947	C73—H732	0.971
C6—C7	1.395 (5)	C73—H731	0.973
C6—H61	0.946	C73—H733	0.962
C7—N8	1.432 (4)	C74—O75	1.215 (4)
N8—C9	1.478 (4)	C74—C76	1.530 (4)
N8—C14	1.355 (4)	C76—O77	1.443 (4)
C9—C10	1.518 (5)	C76—C81	1.543 (4)
C9—H92	0.970	C76—H761	0.970
C9—H91	0.964	O77—C78	1.371 (4)
C10—N11	1.494 (4)	C78—O79	1.204 (4)
C10—H102	0.972	C78—C80	1.483 (5)
C10—H101	0.958	C80—H802	0.940
N11—C12	1.485 (4)	C80—H801	0.948
N11—C13	1.490 (4)	C80—H803	0.957
N11—H111	0.892 (18)	C81—C82	1.517 (4)
C12—H122	0.950	C81—H811	0.969
C12—H123	0.959	C82—C83	1.374 (5)
C12—H121	0.948	C82—C87	1.399 (4)
C13—H133	0.960	C83—C84	1.395 (5)
C13—H131	0.968	C83—H831	0.935
C13—H132	0.962	C84—C85	1.392 (4)
C14—O15	1.220 (4)	C84—H841	0.925
C14—C16	1.533 (4)	C85—C86	1.387 (5)
C16—O17	1.444 (4)	C85—O88	1.368 (4)
C16—C21	1.542 (4)	C86—C87	1.388 (4)
C16—H161	0.978	C86—H861	0.930
O17—C18	1.361 (4)	C87—H871	0.933
C18—O19	1.213 (4)	O88—C89	1.439 (5)
C18—C20	1.480 (5)	C89—H892	0.948
C20—H203	0.947	C89—H891	0.961
C20—H201	0.949	C89—H893	0.961
C20—H202	0.947	S91—C92	1.776 (3)
C21—C22	1.511 (4)	S91—C111	1.844 (3)
C21—H211	0.966	C92—C93	1.387 (5)
C22—C23	1.377 (4)	C92—C97	1.408 (4)
C22—C27	1.405 (4)	C93—C94	1.392 (5)
C23—C24	1.399 (4)	C93—H931	0.939
C23—H231	0.944	C94—C95	1.375 (6)
C24—C25	1.389 (4)	C94—H941	0.939
C24—H241	0.928	C95—C96	1.386 (6)
C25—C26	1.395 (4)	C95—H951	0.953
C25—O28	1.365 (4)	C96—C97	1.385 (5)
C26—C27	1.383 (4)	C96—H961	0.947
C26—H261	0.930	C97—N98	1.428 (4)
C27—H271	0.929	N98—C99	1.473 (4)
O28—C29	1.438 (4)	N98—C104	1.356 (4)
C29—H293	0.945	C99—C100	1.525 (4)
C29—H291	0.964	C99—H991	0.973
C29—H292	0.946	C99—H992	0.971
S31—C32	1.772 (3)	C100—N101	1.487 (4)
S31—C51	1.844 (4)	C100—H1001	0.963
C32—C33	1.395 (4)	C100—H1002	0.980
C32—C37	1.402 (4)	N101—C102	1.476 (5)
C33—C34	1.390 (5)	N101—C103	1.494 (4)
C33—H331	0.941	N101—H1011	0.889 (18)
C34—C35	1.385 (5)	C102—H1022	0.955
C34—H341	0.939	C102—H1021	0.952
C35—C36	1.387 (5)	C102—H1023	0.956
C35—H351	0.943	C103—H1032	0.952
C36—C37	1.381 (4)	C103—H1033	0.956
C36—H361	0.925	C103—H1031	0.953
C37—N38	1.435 (4)	C104—O105	1.223 (4)
N38—C39	1.477 (3)	C104—C106	1.533 (4)
N38—C44	1.351 (4)	C106—O107	1.445 (4)
C39—C40	1.531 (4)	C106—C111	1.544 (4)
C39—H391	0.951	C106—H1061	0.981
C39—H392	0.968	O107—C108	1.362 (4)
C40—N41	1.500 (3)	C108—O109	1.201 (4)
C40—H401	0.961	C108—C110	1.488 (5)
C40—H402	0.978	C110—H1102	0.939
N41—C42	1.487 (4)	C110—H1103	0.946
N41—C43	1.482 (4)	C110—H1101	0.944
N41—H411	0.885 (18)	C111—C112	1.509 (4)
C42—H423	0.972	C111—H1111	0.975
C42—H421	0.976	C112—C113	1.380 (5)
C42—H422	0.976	C112—C117	1.406 (4)
C43—H431	0.968	C113—C114	1.394 (5)
C43—H433	0.959	C113—H1131	0.939
C43—H432	0.968	C114—C115	1.396 (4)
C44—O45	1.223 (4)	C114—H1141	0.917
C44—C46	1.530 (4)	C115—C116	1.379 (5)
C46—O47	1.444 (4)	C115—O118	1.364 (4)
C46—C51	1.542 (4)	C116—C117	1.388 (5)
C46—H461	0.959	C116—H1161	0.936
O47—C48	1.372 (4)	C117—H1171	0.928
C48—O49	1.208 (4)	O118—C119	1.434 (4)
C48—C50	1.470 (5)	C119—H1192	0.947
C50—H501	0.949	C119—H1193	0.938
C50—H503	0.943	C119—H1191	0.956
C50—H502	0.947	P121—O122	1.573 (3)
C51—C52	1.516 (4)	P121—O123	1.563 (2)
C51—H511	0.988	P121—O124	1.503 (2)
C52—C53	1.381 (4)	P121—O125	1.501 (2)
C52—C57	1.392 (4)	O122—H1221	0.849 (19)
C53—C54	1.400 (4)	O123—H1231	0.824 (19)
C53—H531	0.934	P126—O127	1.505 (3)
C54—C55	1.394 (4)	P126—O128	1.505 (2)
C54—H541	0.928	P126—O129	1.571 (2)
C55—C56	1.392 (4)	P126—O130	1.562 (3)
C55—O58	1.367 (4)	O129—H1291	0.837 (19)
C56—C57	1.388 (4)	O130—H1301	0.822 (19)
C56—H561	0.935	P131—O132	1.576 (2)
C57—H571	0.928	P131—O133	1.561 (2)
O58—C59	1.437 (4)	P131—O134	1.515 (3)
C59—H591	0.963	P131—O135	1.499 (2)
C59—H593	0.945	O132—H1321	0.845 (18)
C59—H592	0.956	O133—H1331	0.864 (19)
S61—C62	1.779 (3)	P136—O137	1.500 (2)
S61—C81	1.845 (3)	P136—O138	1.572 (3)
C62—C63	1.384 (5)	P136—O139	1.516 (2)
C62—C67	1.413 (4)	P136—O140	1.571 (2)
C63—C64	1.386 (5)	O138—H1381	0.830 (18)
C63—H631	0.924	O140—H1401	0.883 (19)
C64—C65	1.379 (5)	O141—H1412	0.822 (18)
C64—H641	0.930	O141—H1411	0.896 (19)
C65—C66	1.386 (5)	O142—H1422	0.889 (19)
C65—H651	0.940	O142—H1421	0.816 (19)
C66—C67	1.382 (5)	O143—H1432	0.796 (19)
C66—H661	0.923	O143—H1431	0.812 (19)
C67—N68	1.420 (4)	O144—H1442	0.821 (19)
N68—C69	1.474 (4)	O144—H1441	0.794 (19)
N68—C74	1.361 (4)	O145—H1452	0.806 (19)
C69—C70	1.538 (4)	O145—H1451	0.814 (19)
C69—H692	0.966	O146—H1462	0.818 (19)
C69—H691	0.952	O146—H1461	0.789 (19)
C2—S1—C21	101.87 (16)	C67—N68—C69	119.0 (2)
S1—C2—C3	119.4 (3)	C67—N68—C74	123.3 (3)
S1—C2—C7	120.8 (2)	C69—N68—C74	117.6 (3)
C3—C2—C7	119.7 (3)	N68—C69—C70	109.6 (3)
C2—C3—C4	120.3 (3)	N68—C69—H692	107.4
C2—C3—H31	119.4	C70—C69—H692	111.0
C4—C3—H31	120.3	N68—C69—H691	109.5
C3—C4—C5	119.8 (3)	C70—C69—H691	111.3
C3—C4—H41	121.3	H692—C69—H691	108.0
C5—C4—H41	118.9	C69—C70—N71	111.6 (3)
C4—C5—C6	120.6 (3)	C69—C70—H702	108.0
C4—C5—H51	121.2	N71—C70—H702	109.6
C6—C5—H51	118.2	C69—C70—H701	108.6
C5—C6—C7	119.9 (3)	N71—C70—H701	108.2
C5—C6—H61	119.8	H702—C70—H701	110.8
C7—C6—H61	120.3	C70—N71—C72	110.3 (2)
C2—C7—C6	119.7 (3)	C70—N71—C73	112.7 (3)
C2—C7—N8	120.6 (3)	C72—N71—C73	109.6 (3)
C6—C7—N8	119.7 (3)	C70—N71—H711	106.3 (14)
C7—N8—C9	118.3 (3)	C72—N71—H711	107.8 (14)
C7—N8—C14	123.5 (2)	C73—N71—H711	110.0 (14)
C9—N8—C14	118.1 (2)	N71—C72—H721	106.8
N8—C9—C10	109.7 (3)	N71—C72—H723	111.5
N8—C9—H92	108.7	H721—C72—H723	111.5
C10—C9—H92	110.8	N71—C72—H722	108.5
N8—C9—H91	108.1	H721—C72—H722	109.0
C10—C9—H91	110.2	H723—C72—H722	109.4
H92—C9—H91	109.2	N71—C73—H732	108.3
C9—C10—N11	111.4 (3)	N71—C73—H731	109.7
C9—C10—H102	110.7	H732—C73—H731	109.2
N11—C10—H102	108.9	N71—C73—H733	109.1
C9—C10—H101	110.1	H732—C73—H733	109.0
N11—C10—H101	108.7	H731—C73—H733	111.5
H102—C10—H101	106.9	N68—C74—O75	123.1 (3)
C10—N11—C12	112.5 (3)	N68—C74—C76	115.2 (3)
C10—N11—C13	110.5 (3)	O75—C74—C76	121.6 (3)
C12—N11—C13	111.5 (3)	C74—C76—O77	109.3 (2)
C10—N11—H111	106.8 (14)	C74—C76—C81	113.8 (3)
C12—N11—H111	107.0 (14)	O77—C76—C81	108.5 (2)
C13—N11—H111	108.3 (14)	C74—C76—H761	109.7
N11—C12—H122	109.9	O77—C76—H761	107.3
N11—C12—H123	109.8	C81—C76—H761	108.0
H122—C12—H123	110.4	C76—O77—C78	113.2 (2)
N11—C12—H121	108.2	O77—C78—O79	121.6 (3)
H122—C12—H121	109.5	O77—C78—C80	113.1 (3)
H123—C12—H121	109.0	O79—C78—C80	125.3 (3)
N11—C13—H133	110.4	C78—C80—H802	108.1
N11—C13—H131	110.9	C78—C80—H801	110.5
H133—C13—H131	110.4	H802—C80—H801	109.5
N11—C13—H132	108.4	C78—C80—H803	110.2
H133—C13—H132	108.9	H802—C80—H803	109.4
H131—C13—H132	107.6	H801—C80—H803	109.1
N8—C14—O15	122.7 (3)	C76—C81—S61	107.8 (2)
N8—C14—C16	115.8 (3)	C76—C81—C82	116.7 (3)
O15—C14—C16	121.3 (3)	S61—C81—C82	107.3 (2)
C14—C16—O17	109.2 (2)	C76—C81—H811	106.0
C14—C16—C21	114.0 (3)	S61—C81—H811	109.2
O17—C16—C21	107.7 (2)	C82—C81—H811	109.8
C14—C16—H161	107.4	C81—C82—C83	122.7 (3)
O17—C16—H161	109.0	C81—C82—C87	118.8 (3)
C21—C16—H161	109.5	C83—C82—C87	118.4 (3)
C16—O17—C18	113.8 (2)	C82—C83—C84	121.8 (3)
O17—C18—O19	121.3 (3)	C82—C83—H831	119.7
O17—C18—C20	114.0 (3)	C84—C83—H831	118.5
O19—C18—C20	124.6 (3)	C83—C84—C85	119.1 (3)
C18—C20—H203	111.1	C83—C84—H841	120.2
C18—C20—H201	110.8	C85—C84—H841	120.7
H203—C20—H201	107.3	C84—C85—C86	119.9 (3)
C18—C20—H202	111.7	C84—C85—O88	123.9 (3)
H203—C20—H202	106.4	C86—C85—O88	116.2 (3)
H201—C20—H202	109.5	C85—C86—C87	120.1 (3)
C16—C21—S1	108.3 (2)	C85—C86—H861	120.0
C16—C21—C22	116.3 (3)	C87—C86—H861	119.9
S1—C21—C22	108.1 (2)	C82—C87—C86	120.6 (3)
C16—C21—H211	105.8	C82—C87—H871	120.3
S1—C21—H211	109.7	C86—C87—H871	119.1
C22—C21—H211	108.5	C85—O88—C89	117.9 (2)
C21—C22—C23	122.4 (3)	O88—C89—H892	107.9
C21—C22—C27	119.5 (3)	O88—C89—H891	109.9
C23—C22—C27	118.1 (3)	H892—C89—H891	109.7
C22—C23—C24	121.9 (3)	O88—C89—H893	109.7
C22—C23—H231	118.8	H892—C89—H893	109.9
C24—C23—H231	119.2	H891—C89—H893	109.7
C23—C24—C25	119.2 (3)	C92—S91—C111	102.24 (15)
C23—C24—H241	120.6	S91—C92—C93	119.6 (3)
C25—C24—H241	120.2	S91—C92—C97	120.6 (3)
C24—C25—C26	119.8 (3)	C93—C92—C97	119.8 (3)
C24—C25—O28	124.2 (3)	C92—C93—C94	119.9 (3)
C26—C25—O28	116.0 (3)	C92—C93—H931	119.9
C25—C26—C27	120.1 (3)	C94—C93—H931	120.2
C25—C26—H261	119.7	C93—C94—C95	120.3 (3)
C27—C26—H261	120.2	C93—C94—H941	121.7
C22—C27—C26	120.9 (3)	C95—C94—H941	118.0
C22—C27—H271	119.5	C94—C95—C96	120.2 (3)
C26—C27—H271	119.6	C94—C95—H951	120.7
C25—O28—C29	117.6 (2)	C96—C95—H951	119.1
O28—C29—H293	107.6	C95—C96—C97	120.5 (3)
O28—C29—H291	109.3	C95—C96—H961	119.1
H293—C29—H291	110.4	C97—C96—H961	120.4
O28—C29—H292	109.5	C92—C97—C96	119.3 (3)
H293—C29—H292	110.7	C92—C97—N98	120.5 (3)
H291—C29—H292	109.2	C96—C97—N98	120.2 (3)
C32—S31—C51	101.47 (16)	C97—N98—C99	118.3 (3)
S31—C32—C33	120.0 (3)	C97—N98—C104	123.4 (3)
S31—C32—C37	121.3 (2)	C99—N98—C104	118.1 (3)
C33—C32—C37	118.7 (3)	N98—C99—C100	110.0 (3)
C32—C33—C34	120.5 (3)	N98—C99—H991	107.6
C32—C33—H331	118.2	C100—C99—H991	110.8
C34—C33—H331	121.3	N98—C99—H992	109.8
C33—C34—C35	120.2 (3)	C100—C99—H992	109.3
C33—C34—H341	119.6	H991—C99—H992	109.3
C35—C34—H341	120.2	C99—C100—N101	111.5 (3)
C34—C35—C36	119.7 (3)	C99—C100—H1001	110.5
C34—C35—H351	121.0	N101—C100—H1001	107.5
C36—C35—H351	119.3	C99—C100—H1002	110.4
C35—C36—C37	120.4 (3)	N101—C100—H1002	109.5
C35—C36—H361	119.9	H1001—C100—H1002	107.4
C37—C36—H361	119.7	C100—N101—C102	112.6 (3)
C32—C37—C36	120.5 (3)	C100—N101—C103	110.3 (3)
C32—C37—N38	119.9 (3)	C102—N101—C103	111.3 (3)
C36—C37—N38	119.7 (3)	C100—N101—H1011	106.7 (14)
C37—N38—C39	118.6 (3)	C102—N101—H1011	107.7 (14)
C37—N38—C44	123.3 (2)	C103—N101—H1011	108.0 (14)
C39—N38—C44	118.0 (2)	N101—C102—H1022	110.2
N38—C39—C40	109.4 (3)	N101—C102—H1021	107.9
N38—C39—H391	110.2	H1022—C102—H1021	108.5
C40—C39—H391	110.6	N101—C102—H1023	110.2
N38—C39—H392	108.0	H1022—C102—H1023	109.7
C40—C39—H392	111.2	H1021—C102—H1023	110.4
H391—C39—H392	107.3	N101—C103—H1032	110.9
C39—C40—N41	111.8 (3)	N101—C103—H1033	109.1
C39—C40—H401	109.1	H1032—C103—H1033	108.2
N41—C40—H401	107.5	N101—C103—H1031	109.9
C39—C40—H402	109.3	H1032—C103—H1031	110.0
N41—C40—H402	108.5	H1033—C103—H1031	108.7
H401—C40—H402	110.6	N98—C104—O105	123.1 (3)
C40—N41—C42	110.6 (2)	N98—C104—C106	116.1 (3)
C40—N41—C43	112.5 (2)	O105—C104—C106	120.7 (3)
C42—N41—C43	109.5 (2)	C104—C106—O107	109.6 (3)
C40—N41—H411	106.6 (14)	C104—C106—C111	113.7 (3)
C42—N41—H411	107.8 (14)	O107—C106—C111	107.7 (2)
C43—N41—H411	109.6 (14)	C104—C106—H1061	108.0
N41—C42—H423	107.1	O107—C106—H1061	108.8
N41—C42—H421	107.1	C111—C106—H1061	109.1
H423—C42—H421	111.0	C106—O107—C108	113.2 (2)
N41—C42—H422	111.0	O107—C108—O109	121.8 (3)
H423—C42—H422	111.4	O107—C108—C110	113.2 (3)
H421—C42—H422	109.2	O109—C108—C110	125.0 (3)
N41—C43—H431	110.4	C108—C110—H1102	109.7
N41—C43—H433	107.9	C108—C110—H1103	113.5
H431—C43—H433	109.1	H1102—C110—H1103	108.7
N41—C43—H432	108.8	C108—C110—H1101	110.0
H431—C43—H432	111.1	H1102—C110—H1101	106.8
H433—C43—H432	109.5	H1103—C110—H1101	108.0
N38—C44—O45	123.1 (3)	C106—C111—S91	108.3 (2)
N38—C44—C46	115.5 (2)	C106—C111—C112	116.6 (3)
O45—C44—C46	121.4 (3)	S91—C111—C112	108.1 (2)
C44—C46—O47	109.2 (2)	C106—C111—H1111	105.4
C44—C46—C51	113.9 (3)	S91—C111—H1111	110.0
O47—C46—C51	108.5 (2)	C112—C111—H1111	108.4
C44—C46—H461	109.0	C111—C112—C113	122.4 (3)
O47—C46—H461	107.6	C111—C112—C117	119.6 (3)
C51—C46—H461	108.4	C113—C112—C117	117.9 (3)
C46—O47—C48	113.4 (2)	C112—C113—C114	121.7 (3)
O47—C48—O49	121.1 (3)	C112—C113—H1131	119.1
O47—C48—C50	113.4 (3)	C114—C113—H1131	119.2
O49—C48—C50	125.5 (3)	C113—C114—C115	119.5 (3)
C48—C50—H501	110.8	C113—C114—H1141	121.2
C48—C50—H503	109.8	C115—C114—H1141	119.3
H501—C50—H503	108.9	C114—C115—C116	119.7 (3)
C48—C50—H502	109.0	C114—C115—O118	124.1 (3)
H501—C50—H502	108.6	C116—C115—O118	116.2 (3)
H503—C50—H502	109.7	C115—C116—C117	120.3 (3)
C46—C51—S31	107.8 (2)	C115—C116—H1161	119.6
C46—C51—C52	116.8 (3)	C117—C116—H1161	120.1
S31—C51—C52	107.6 (2)	C112—C117—C116	120.9 (3)
C46—C51—H511	105.3	C112—C117—H1171	119.7
S31—C51—H511	108.8	C116—C117—H1171	119.4
C52—C51—H511	110.3	C115—O118—C119	118.5 (2)
C51—C52—C53	122.3 (3)	O118—C119—H1192	109.3
C51—C52—C57	119.2 (3)	O118—C119—H1193	109.1
C53—C52—C57	118.3 (3)	H1192—C119—H1193	109.2
C52—C53—C54	121.8 (3)	O118—C119—H1191	109.8
C52—C53—H531	119.9	H1192—C119—H1191	108.5
C54—C53—H531	118.3	H1193—C119—H1191	110.8
C53—C54—C55	118.9 (3)	O122—P121—O123	103.48 (14)
C53—C54—H541	120.7	O122—P121—O124	108.27 (16)
C55—C54—H541	120.4	O123—P121—O124	110.15 (14)
C54—C55—C56	119.9 (3)	O122—P121—O125	109.41 (15)
C54—C55—O58	124.2 (3)	O123—P121—O125	111.67 (14)
C56—C55—O58	115.9 (3)	O124—P121—O125	113.34 (13)
C55—C56—C57	120.0 (3)	P121—O122—H1221	122 (4)
C55—C56—H561	119.7	P121—O123—H1231	109 (4)
C57—C56—H561	120.3	O127—P126—O128	113.77 (13)
C52—C57—C56	121.0 (3)	O127—P126—O129	108.07 (16)
C52—C57—H571	119.8	O128—P126—O129	109.25 (14)
C56—C57—H571	119.2	O127—P126—O130	110.09 (15)
C55—O58—C59	117.9 (2)	O128—P126—O130	111.59 (14)
O58—C59—H591	110.0	O129—P126—O130	103.50 (13)
O58—C59—H593	107.7	P126—O129—H1291	119 (4)
H591—C59—H593	109.4	P126—O130—H1301	110 (3)
O58—C59—H592	110.2	O132—P131—O133	106.74 (13)
H591—C59—H592	109.4	O132—P131—O134	108.84 (13)
H593—C59—H592	110.1	O133—P131—O134	111.17 (15)
C62—S61—C81	101.58 (15)	O132—P131—O135	108.69 (14)
S61—C62—C63	120.3 (3)	O133—P131—O135	107.00 (13)
S61—C62—C67	120.5 (3)	O134—P131—O135	114.12 (14)
C63—C62—C67	119.2 (3)	P131—O132—H1321	115 (3)
C62—C63—C64	120.7 (3)	P131—O133—H1331	114 (3)
C62—C63—H631	119.3	O137—P136—O138	108.98 (13)
C64—C63—H631	120.0	O137—P136—O139	114.35 (15)
C63—C64—C65	119.9 (3)	O138—P136—O139	108.43 (14)
C63—C64—H641	118.4	O137—P136—O140	106.93 (13)
C65—C64—H641	121.7	O138—P136—O140	106.76 (14)
C64—C65—C66	120.3 (3)	O139—P136—O140	111.12 (14)
C64—C65—H651	120.5	P136—O138—H1381	115 (3)
C66—C65—H651	119.2	P136—O140—H1401	114 (3)
C65—C66—C67	120.5 (3)	H1412—O141—H1411	104.8 (10)
C65—C66—H661	120.2	H1422—O142—H1421	105.1 (10)
C67—C66—H661	119.4	H1432—O143—H1431	115 (5)
C62—C67—C66	119.4 (3)	H1442—O144—H1441	91 (5)
C62—C67—N68	120.5 (3)	H1452—O145—H1451	120 (5)
C66—C67—N68	120.0 (3)	H1462—O146—H1461	84 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H51···O124	0.95	2.49	3.370 (5)	154
C9—H92···O49	0.97	2.44	3.405 (5)	177
N11—H111···O139	0.89	1.75	2.637 (5)	175 (2)
C12—H122···O49	0.95	2.49	3.438 (5)	174
C20—H203···O45^i	0.95	2.38	3.204 (5)	145
C20—H201···O88^ii	0.95	2.49	3.255 (5)	138
C39—H391···O19^iii	0.95	2.40	3.349 (5)	178
C40—H401···O138	0.96	2.48	3.346 (5)	150
N41—H411···O141^iii	0.89	1.82	2.696 (5)	169 (2)
C42—H423···O138	0.97	2.54	3.410 (5)	149
C42—H421···O133^iii	0.98	2.53	3.283 (5)	134
C43—H431···O19^iii	0.97	2.39	3.362 (5)	178
C50—H501···O15	0.95	2.50	3.179 (5)	129
C50—H502···O118^ii	0.95	2.37	3.257 (5)	155
C69—H691···O109	0.95	2.41	3.357 (5)	178
C70—H701···O132^iv	0.97	2.48	3.346 (5)	149
N71—H711···O142^v	0.89	1.82	2.698 (5)	169 (2)
C72—H721···O132^iv	0.97	2.52	3.409 (5)	152
C72—H722···O140^iv	0.97	2.50	3.276 (5)	137
C73—H731···O109	0.97	2.39	3.366 (5)	176
C80—H801···O58^vi	0.95	2.35	3.254 (5)	160
C80—H803···O105^i	0.96	2.53	3.179 (5)	126
C95—H951···O127^vii	0.95	2.49	3.370 (5)	153
C99—H992···O79^iii	0.97	2.44	3.413 (5)	176
N101—H1011···O134^v	0.89	1.74	2.630 (5)	175 (2)
C102—H1023···O79^iii	0.96	2.49	3.441 (5)	176
C110—H1102···O28^viii	0.94	2.41	3.251 (5)	149
C110—H1101···O75	0.94	2.44	3.209 (5)	138
O122—H1221···O135	0.85	1.69	2.538 (5)	177 (6)
O123—H1231···O143	0.82	1.80	2.603 (5)	163 (5)
O129—H1291···O137^vi	0.84	1.71	2.542 (5)	173 (5)
O130—H1301···O145	0.82	1.81	2.605 (5)	163 (5)
O132—H1321···O125^ii	0.85	1.71	2.555 (5)	175 (4)
O133—H1331···O124^ii	0.86	1.67	2.498 (5)	160 (5)
O138—H1381···O128^iii	0.83	1.73	2.557 (5)	177 (5)
O140—H1401···O127^iii	0.88	1.63	2.496 (5)	167 (5)
O141—H1412···O144^i	0.82	1.94	2.750 (5)	169 (5)
O141—H1411···O135	0.90	1.96	2.831 (5)	164 (5)
O142—H1422···O137^i	0.89	1.95	2.827 (5)	171 (5)
O142—H1421···O146^ix	0.82	1.95	2.747 (5)	167 (5)
O143—H1432···O139	0.80	1.94	2.702 (5)	159 (5)
O143—H1431···O129^iii	0.81	2.29	3.049 (5)	156 (5)
O144—H1442···O128^iii	0.82	2.02	2.805 (5)	160 (5)
O144—H1441···O124^iii	0.79	1.99	2.762 (5)	166 (5)
O145—H1452···O134^viii	0.81	2.03	2.700 (5)	141 (5)
O145—H1451···O122	0.81	2.26	3.054 (5)	164 (5)
O146—H1462···O125	0.82	2.01	2.814 (5)	167 (5)
O146—H1461···O127^iii	0.79	2.04	2.759 (5)	150 (5)

Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z; (iii) x, y−1, z; (iv) x−1, y, z+1; (v) x−1, y−1, z+1; (vi) x−1, y+1, z; (vii) x, y−1, z+1; (viii) x−1, y, z; (ix) x+1, y+1, z.

(pn180815_uo_eph_1_180814_pyrolidcarbox)

Crystal data

C10H16NO·C5H6NO3·H2O	F(000) = 336
Mr = 312.36	Dx = 1.354 Mg m^−3
Monoclinic, P21	Cu Kα radiation, λ = 1.54184 Å
a = 11.47377 (11) Å	Cell parameters from 12100 reflections
b = 6.14747 (5) Å	θ = 4.1–78.6°
c = 11.71348 (12) Å	µ = 0.84 mm^−1
β = 111.9780 (11)°	T = 160 K
V = 766.16 (1) Å^3	Needle, colourless
Z = 2	0.38 × 0.04 × 0.03 mm

Data collection

XtaLAB Synergy, Dualflex, Pilatus 200K diffractometer	3268 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source	3223 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.024
ω scans	θmax = 78.9°, θmin = 4.1°
Absorption correction: gaussian CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −14→14
Tmin = 0.708, Tmax = 1.000	k = −7→7
13893 measured reflections	l = −14→14

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.025	w = 1/[σ^2(Fo^2) + (0.0385P)^2 + 0.1159P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.066	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 0.20 e Å^−3
3268 reflections	Δρmin = −0.14 e Å^−3
205 parameters	Absolute structure: Flack x determined using 1425 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
1 restraint	Absolute structure parameter: 0.03 (5)

Special details

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.36233 (10)	0.63183 (19)	0.82268 (10)	0.0217 (2)
H1	0.3939	0.5443	0.7872	0.033*
O2	0.45666 (11)	0.3683 (2)	0.70244 (10)	0.0306 (3)
O3	0.57405 (10)	0.21348 (19)	0.88122 (9)	0.0196 (2)
O4	0.86010 (11)	−0.2218 (2)	0.83263 (11)	0.0256 (3)
O5	1.02189 (12)	−0.1350 (2)	1.07667 (11)	0.0293 (3)
H5A	1.0501	−0.0085	1.1011	0.044*
H5B	0.9727	−0.1295	1.0016	0.044*
N1	0.36998 (11)	1.0452 (2)	0.93810 (11)	0.0156 (2)
H1A	0.3950	0.9283	0.9891	0.019*
H1B	0.4371	1.0910	0.9210	0.019*
N2	0.76034 (11)	0.1063 (2)	0.79509 (12)	0.0187 (3)
H2A	0.8178	0.1761	0.8558	0.022*
C1	0.32586 (13)	0.8239 (2)	0.75197 (13)	0.0164 (3)
H1C	0.4032	0.8957	0.7498	0.020*
C2	0.26721 (13)	0.9748 (2)	0.81993 (13)	0.0158 (3)
H2	0.2334	1.1065	0.7679	0.019*
C3	0.16114 (13)	0.8683 (3)	0.84745 (14)	0.0214 (3)
H3A	0.1955	0.7539	0.9092	0.032*
H3B	0.1006	0.8045	0.7718	0.032*
H3C	0.1188	0.9779	0.8790	0.032*
C4	0.33182 (15)	1.2229 (3)	1.00359 (15)	0.0235 (3)
H4A	0.3077	1.3517	0.9506	0.035*
H4B	0.4024	1.2593	1.0797	0.035*
H4C	0.2603	1.1744	1.0235	0.035*
C5	0.23581 (13)	0.7874 (2)	0.62021 (13)	0.0164 (3)
C6	0.21765 (14)	0.9537 (2)	0.53407 (14)	0.0190 (3)
H6	0.2617	1.0872	0.5584	0.023*
C7	0.13549 (15)	0.9251 (3)	0.41288 (14)	0.0216 (3)
H7	0.1230	1.0393	0.3549	0.026*
C8	0.07161 (14)	0.7291 (3)	0.37662 (14)	0.0229 (3)
H8	0.0164	0.7087	0.2936	0.027*
C9	0.08861 (14)	0.5641 (3)	0.46157 (14)	0.0235 (3)
H9	0.0444	0.4308	0.4370	0.028*
C10	0.17063 (14)	0.5929 (3)	0.58338 (14)	0.0203 (3)
H10	0.1820	0.4791	0.6414	0.024*
C11	0.55185 (13)	0.2692 (2)	0.77137 (13)	0.0168 (3)
C12	0.64694 (13)	0.2113 (3)	0.71199 (13)	0.0176 (3)
H12	0.6706	0.3467	0.6785	0.021*
C13	0.59343 (14)	0.0436 (3)	0.60660 (14)	0.0222 (3)
H13A	0.5008	0.0339	0.5791	0.027*
H13B	0.6157	0.0835	0.5354	0.027*
C14	0.65528 (14)	−0.1711 (3)	0.66342 (15)	0.0231 (3)
H14A	0.5981	−0.2592	0.6904	0.028*
H14B	0.6790	−0.2566	0.6038	0.028*
C15	0.77080 (14)	−0.1031 (3)	0.77253 (13)	0.0179 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0274 (5)	0.0199 (5)	0.0175 (5)	0.0087 (4)	0.0082 (4)	0.0016 (4)
O2	0.0307 (6)	0.0397 (7)	0.0218 (5)	0.0189 (5)	0.0101 (5)	0.0037 (5)
O3	0.0226 (5)	0.0205 (5)	0.0175 (5)	−0.0002 (4)	0.0096 (4)	−0.0005 (4)
O4	0.0234 (5)	0.0267 (6)	0.0241 (5)	0.0091 (4)	0.0059 (4)	0.0031 (5)
O5	0.0337 (6)	0.0237 (6)	0.0238 (6)	0.0028 (5)	0.0031 (5)	0.0033 (5)
N1	0.0167 (5)	0.0161 (6)	0.0147 (5)	0.0007 (4)	0.0067 (4)	−0.0001 (4)
N2	0.0157 (5)	0.0194 (7)	0.0200 (6)	0.0001 (5)	0.0055 (5)	−0.0034 (5)
C1	0.0166 (6)	0.0176 (7)	0.0159 (6)	0.0010 (5)	0.0070 (5)	−0.0002 (5)
C2	0.0163 (6)	0.0166 (7)	0.0140 (6)	0.0017 (5)	0.0050 (5)	0.0000 (5)
C3	0.0166 (6)	0.0279 (8)	0.0210 (7)	0.0002 (6)	0.0086 (5)	−0.0006 (6)
C4	0.0267 (7)	0.0229 (8)	0.0223 (7)	0.0011 (6)	0.0109 (6)	−0.0065 (6)
C5	0.0154 (6)	0.0199 (7)	0.0153 (6)	0.0006 (5)	0.0073 (5)	−0.0011 (5)
C6	0.0203 (7)	0.0201 (7)	0.0187 (7)	−0.0020 (6)	0.0099 (6)	0.0000 (6)
C7	0.0215 (7)	0.0266 (8)	0.0179 (7)	0.0018 (6)	0.0088 (6)	0.0039 (6)
C8	0.0184 (7)	0.0333 (9)	0.0160 (7)	−0.0010 (6)	0.0055 (5)	−0.0038 (6)
C9	0.0218 (7)	0.0250 (8)	0.0232 (7)	−0.0042 (6)	0.0080 (6)	−0.0058 (6)
C10	0.0222 (7)	0.0193 (8)	0.0198 (7)	−0.0021 (5)	0.0082 (6)	0.0006 (6)
C11	0.0196 (6)	0.0152 (7)	0.0167 (6)	0.0007 (5)	0.0081 (5)	−0.0020 (5)
C12	0.0192 (6)	0.0174 (6)	0.0179 (6)	0.0022 (5)	0.0089 (5)	0.0019 (5)
C13	0.0231 (7)	0.0271 (8)	0.0151 (7)	0.0076 (6)	0.0057 (5)	−0.0009 (6)
C14	0.0213 (7)	0.0211 (8)	0.0241 (7)	0.0023 (6)	0.0052 (6)	−0.0051 (6)
C15	0.0188 (7)	0.0201 (7)	0.0169 (6)	0.0020 (5)	0.0091 (5)	0.0012 (5)

Geometric parameters (Å, º)

O1—H1	0.8400	C4—H4B	0.9800
O1—C1	1.4127 (18)	C4—H4C	0.9800
O2—C11	1.2471 (19)	C5—C6	1.396 (2)
O3—C11	1.2621 (18)	C5—C10	1.390 (2)
O4—C15	1.2401 (19)	C6—H6	0.9500
O5—H5A	0.8503	C6—C7	1.390 (2)
O5—H5B	0.8496	C7—H7	0.9500
N1—H1A	0.9100	C7—C8	1.392 (2)
N1—H1B	0.9100	C8—H8	0.9500
N1—C2	1.5073 (18)	C8—C9	1.383 (2)
N1—C4	1.4914 (19)	C9—H9	0.9500
N2—H2A	0.8800	C9—C10	1.396 (2)
N2—C12	1.4522 (19)	C10—H10	0.9500
N2—C15	1.329 (2)	C11—C12	1.5391 (19)
C1—H1C	1.0000	C12—H12	1.0000
C1—C2	1.5324 (19)	C12—C13	1.548 (2)
C1—C5	1.5187 (19)	C13—H13A	0.9900
C2—H2	1.0000	C13—H13B	0.9900
C2—C3	1.519 (2)	C13—C14	1.528 (2)
C3—H3A	0.9800	C14—H14A	0.9900
C3—H3B	0.9800	C14—H14B	0.9900
C3—H3C	0.9800	C14—C15	1.515 (2)
C4—H4A	0.9800
C1—O1—H1	109.5	C7—C6—C5	120.40 (14)
H5A—O5—H5B	109.5	C7—C6—H6	119.8
H1A—N1—H1B	107.7	C6—C7—H7	120.0
C2—N1—H1A	108.8	C6—C7—C8	119.96 (14)
C2—N1—H1B	108.8	C8—C7—H7	120.0
C4—N1—H1A	108.8	C7—C8—H8	120.0
C4—N1—H1B	108.8	C9—C8—C7	119.95 (14)
C4—N1—C2	113.79 (11)	C9—C8—H8	120.0
C12—N2—H2A	122.5	C8—C9—H9	119.9
C15—N2—H2A	122.5	C8—C9—C10	120.13 (15)
C15—N2—C12	114.99 (13)	C10—C9—H9	119.9
O1—C1—H1C	108.2	C5—C10—C9	120.34 (14)
O1—C1—C2	107.02 (11)	C5—C10—H10	119.8
O1—C1—C5	114.32 (12)	C9—C10—H10	119.8
C2—C1—H1C	108.2	O2—C11—O3	125.89 (13)
C5—C1—H1C	108.2	O2—C11—C12	114.68 (13)
C5—C1—C2	110.69 (11)	O3—C11—C12	119.42 (13)
N1—C2—C1	107.83 (11)	N2—C12—C11	114.13 (12)
N1—C2—H2	108.6	N2—C12—H12	109.1
N1—C2—C3	110.03 (11)	N2—C12—C13	103.12 (12)
C1—C2—H2	108.6	C11—C12—H12	109.1
C3—C2—C1	113.07 (12)	C11—C12—C13	112.20 (12)
C3—C2—H2	108.6	C13—C12—H12	109.1
C2—C3—H3A	109.5	C12—C13—H13A	110.9
C2—C3—H3B	109.5	C12—C13—H13B	110.9
C2—C3—H3C	109.5	H13A—C13—H13B	108.9
H3A—C3—H3B	109.5	C14—C13—C12	104.29 (12)
H3A—C3—H3C	109.5	C14—C13—H13A	110.9
H3B—C3—H3C	109.5	C14—C13—H13B	110.9
N1—C4—H4A	109.5	C13—C14—H14A	110.9
N1—C4—H4B	109.5	C13—C14—H14B	110.9
N1—C4—H4C	109.5	H14A—C14—H14B	108.9
H4A—C4—H4B	109.5	C15—C14—C13	104.26 (13)
H4A—C4—H4C	109.5	C15—C14—H14A	110.9
H4B—C4—H4C	109.5	C15—C14—H14B	110.9
C6—C5—C1	119.14 (14)	O4—C15—N2	125.04 (15)
C10—C5—C1	121.65 (13)	O4—C15—C14	126.35 (15)
C10—C5—C6	119.20 (13)	N2—C15—C14	108.61 (13)
C5—C6—H6	119.8
O1—C1—C2—N1	67.64 (14)	C5—C1—C2—C3	70.95 (15)
O1—C1—C2—C3	−54.23 (15)	C5—C6—C7—C8	−0.6 (2)
O1—C1—C5—C6	−164.37 (12)	C6—C5—C10—C9	0.4 (2)
O1—C1—C5—C10	15.91 (19)	C6—C7—C8—C9	0.9 (2)
O2—C11—C12—N2	176.92 (14)	C7—C8—C9—C10	−0.6 (2)
O2—C11—C12—C13	−66.24 (18)	C8—C9—C10—C5	0.0 (2)
O3—C11—C12—N2	−3.8 (2)	C10—C5—C6—C7	−0.1 (2)
O3—C11—C12—C13	113.00 (15)	C11—C12—C13—C14	−103.01 (14)
N2—C12—C13—C14	20.25 (15)	C12—N2—C15—O4	−179.94 (14)
C1—C5—C6—C7	−179.80 (13)	C12—N2—C15—C14	−0.81 (17)
C1—C5—C10—C9	−179.92 (13)	C12—C13—C14—C15	−20.88 (15)
C2—C1—C5—C6	74.69 (16)	C13—C14—C15—O4	−166.74 (15)
C2—C1—C5—C10	−105.03 (15)	C13—C14—C15—N2	14.15 (16)
C4—N1—C2—C1	169.88 (12)	C15—N2—C12—C11	109.32 (15)
C4—N1—C2—C3	−66.38 (16)	C15—N2—C12—C13	−12.66 (16)
C5—C1—C2—N1	−167.18 (11)

(pn180815_uo_traz_1_180814_c6_nitrate_mo)

Crystal data

C19H23ClN5O·NO3	F(000) = 912
Mr = 434.88	Dx = 1.442 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.6065 (3) Å	Cell parameters from 14972 reflections
b = 13.0726 (3) Å	θ = 2.6–33.0°
c = 12.6694 (3) Å	µ = 0.23 mm^−1
β = 106.397 (3)°	T = 160 K
V = 2003.00 (8) Å^3	Block, colourless
Z = 4	0.53 × 0.20 × 0.17 mm

Data collection

XtaLAB Synergy, Dualflex, Pilatus 200K diffractometer	6532 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Mo) X-ray Source	5530 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.020
ω scans	θmax = 33.2°, θmin = 2.3°
Absorption correction: gaussian CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −16→19
Tmin = 0.560, Tmax = 1.000	k = −18→20
21495 measured reflections	l = −19→18

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.106	w = 1/[σ^2(Fo^2) + (0.0584P)^2 + 0.3895P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
6532 reflections	Δρmax = 0.40 e Å^−3
274 parameters	Δρmin = −0.29 e Å^−3
0 restraints

Special details

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl26	0.82838 (3)	1.05094 (2)	0.83765 (2)	0.03897 (8)
O10	0.09502 (7)	0.67054 (7)	0.12314 (7)	0.03800 (18)
O28	0.43563 (8)	0.51734 (7)	0.27552 (7)	0.0426 (2)
O29	0.53436 (7)	0.39815 (5)	0.37420 (6)	0.03386 (17)
O30	0.55841 (8)	0.55663 (6)	0.42729 (8)	0.0445 (2)
N2	0.03849 (7)	0.65742 (6)	0.28322 (7)	0.02562 (16)
N3	−0.04645 (7)	0.69337 (7)	0.32215 (6)	0.02694 (16)
N8	−0.06210 (6)	0.74893 (6)	0.15201 (6)	0.02094 (14)
N14	0.39661 (6)	0.72816 (6)	0.41840 (6)	0.02118 (14)
H14	0.4366 (10)	0.6718 (10)	0.4492 (10)	0.025*
N17	0.56757 (6)	0.88233 (6)	0.49464 (6)	0.02097 (14)
N27	0.51008 (7)	0.49074 (6)	0.35862 (7)	0.02418 (15)
C1	0.03291 (8)	0.68863 (7)	0.17939 (7)	0.02428 (17)
C4	−0.20601 (9)	0.80342 (8)	0.22989 (9)	0.0313 (2)
H4	−0.2392	0.8051	0.2885	0.038*
C5	−0.25250 (9)	0.85343 (8)	0.13448 (10)	0.0338 (2)
H5	−0.3193	0.8902	0.1263	0.041*
C6	−0.20331 (9)	0.85218 (8)	0.04575 (9)	0.0312 (2)
H6	−0.2375	0.8882	−0.0202	0.037*
C7	−0.10896 (8)	0.80034 (8)	0.05485 (7)	0.02650 (18)
H7	−0.0757	0.7992	−0.0037	0.032*
C9	−0.10625 (8)	0.74827 (7)	0.24034 (7)	0.02249 (16)
C11	0.11892 (9)	0.58567 (8)	0.34778 (10)	0.0339 (2)
H11A	0.1424	0.5388	0.2973	0.041*
H11B	0.0833	0.5440	0.3935	0.041*
C12	0.22069 (8)	0.63785 (8)	0.42241 (9)	0.0301 (2)
H12A	0.1978	0.6877	0.4706	0.036*
H12B	0.2690	0.5862	0.4697	0.036*
C13	0.28392 (8)	0.69255 (7)	0.35340 (7)	0.02533 (17)
H13A	0.2919	0.6458	0.2946	0.030*
H13B	0.2403	0.7524	0.3175	0.030*
C15	0.39353 (8)	0.80252 (7)	0.50691 (7)	0.02247 (16)
H15A	0.3591	0.7695	0.5594	0.027*
H15B	0.3473	0.8619	0.4739	0.027*
C16	0.50821 (8)	0.83947 (7)	0.56830 (7)	0.02320 (17)
H16A	0.5021	0.8923	0.6223	0.028*
H16B	0.5512	0.7815	0.6095	0.028*
C18	0.56703 (8)	0.81464 (7)	0.40203 (7)	0.02380 (17)
H18A	0.6145	0.7546	0.4298	0.029*
H18B	0.5987	0.8516	0.3498	0.029*
C19	0.45226 (8)	0.77845 (7)	0.34223 (7)	0.02467 (17)
H19A	0.4074	0.8375	0.3062	0.030*
H19B	0.4567	0.7293	0.2841	0.030*
C20	0.66838 (7)	0.93099 (6)	0.54464 (7)	0.02075 (16)
C21	0.69872 (8)	0.95883 (7)	0.65659 (7)	0.02364 (17)
H21	0.6526	0.9413	0.7015	0.028*
C22	0.79649 (8)	1.01202 (7)	0.70079 (8)	0.02620 (18)
C23	0.86837 (9)	1.03794 (8)	0.64059 (9)	0.0299 (2)
H23	0.9352	1.0737	0.6731	0.036*
C24	0.83867 (9)	1.00945 (8)	0.53037 (9)	0.0305 (2)
H24	0.8865	1.0258	0.4867	0.037*
C25	0.74116 (8)	0.95790 (7)	0.48290 (8)	0.02630 (18)
H25	0.7229	0.9403	0.4071	0.032*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl26	0.04455 (17)	0.04064 (15)	0.02811 (12)	−0.00862 (11)	0.00436 (10)	−0.00800 (9)
O10	0.0306 (4)	0.0492 (5)	0.0372 (4)	0.0088 (3)	0.0144 (3)	−0.0083 (3)
O28	0.0528 (5)	0.0350 (4)	0.0297 (4)	0.0083 (4)	−0.0052 (3)	0.0042 (3)
O29	0.0411 (4)	0.0230 (3)	0.0345 (4)	0.0092 (3)	0.0059 (3)	−0.0015 (3)
O30	0.0398 (5)	0.0305 (4)	0.0524 (5)	−0.0073 (3)	−0.0043 (4)	−0.0118 (3)
N2	0.0215 (4)	0.0264 (4)	0.0261 (3)	0.0021 (3)	0.0021 (3)	0.0030 (3)
N3	0.0254 (4)	0.0323 (4)	0.0233 (3)	−0.0012 (3)	0.0072 (3)	0.0022 (3)
N8	0.0197 (4)	0.0242 (3)	0.0187 (3)	0.0018 (3)	0.0049 (3)	−0.0010 (3)
N14	0.0211 (4)	0.0176 (3)	0.0228 (3)	0.0021 (3)	0.0029 (3)	0.0009 (2)
N17	0.0249 (4)	0.0190 (3)	0.0206 (3)	−0.0019 (3)	0.0090 (3)	−0.0010 (2)
N27	0.0233 (4)	0.0220 (3)	0.0268 (3)	−0.0006 (3)	0.0063 (3)	0.0000 (3)
C1	0.0207 (4)	0.0269 (4)	0.0240 (4)	0.0020 (3)	0.0044 (3)	−0.0036 (3)
C4	0.0259 (5)	0.0313 (5)	0.0408 (5)	0.0014 (4)	0.0158 (4)	−0.0051 (4)
C5	0.0218 (5)	0.0252 (4)	0.0516 (6)	0.0032 (3)	0.0060 (4)	−0.0011 (4)
C6	0.0276 (5)	0.0240 (4)	0.0346 (5)	−0.0021 (3)	−0.0033 (4)	0.0043 (4)
C7	0.0277 (5)	0.0285 (4)	0.0202 (4)	−0.0035 (3)	0.0018 (3)	0.0013 (3)
C9	0.0219 (4)	0.0240 (4)	0.0228 (4)	−0.0014 (3)	0.0083 (3)	−0.0021 (3)
C11	0.0249 (5)	0.0246 (4)	0.0434 (5)	−0.0016 (4)	−0.0046 (4)	0.0098 (4)
C12	0.0238 (5)	0.0297 (4)	0.0313 (4)	−0.0029 (3)	−0.0012 (4)	0.0093 (4)
C13	0.0209 (4)	0.0264 (4)	0.0251 (4)	−0.0003 (3)	0.0007 (3)	0.0002 (3)
C15	0.0247 (4)	0.0208 (4)	0.0230 (4)	−0.0007 (3)	0.0085 (3)	−0.0004 (3)
C16	0.0261 (4)	0.0240 (4)	0.0206 (3)	−0.0041 (3)	0.0084 (3)	−0.0005 (3)
C18	0.0245 (4)	0.0244 (4)	0.0234 (4)	0.0004 (3)	0.0084 (3)	−0.0036 (3)
C19	0.0256 (4)	0.0276 (4)	0.0210 (4)	0.0001 (3)	0.0068 (3)	−0.0015 (3)
C20	0.0239 (4)	0.0157 (3)	0.0234 (4)	0.0013 (3)	0.0080 (3)	0.0015 (3)
C21	0.0280 (4)	0.0202 (4)	0.0233 (4)	−0.0009 (3)	0.0082 (3)	0.0014 (3)
C22	0.0295 (5)	0.0209 (4)	0.0260 (4)	0.0003 (3)	0.0043 (3)	0.0000 (3)
C23	0.0253 (5)	0.0262 (4)	0.0366 (5)	−0.0025 (3)	0.0063 (4)	0.0011 (4)
C24	0.0288 (5)	0.0298 (5)	0.0363 (5)	−0.0029 (4)	0.0144 (4)	0.0019 (4)
C25	0.0298 (5)	0.0253 (4)	0.0264 (4)	−0.0020 (3)	0.0122 (4)	0.0001 (3)

Geometric parameters (Å, º)

Cl26—C22	1.7417 (10)	N17—C18	1.4680 (11)
O10—C1	1.2215 (11)	N17—C20	1.4023 (12)
O28—N27	1.2459 (11)	C4—C5	1.3535 (16)
O29—N27	1.2505 (10)	C4—C9	1.4230 (13)
O30—N27	1.2533 (11)	C5—C6	1.4290 (17)
N2—N3	1.3818 (12)	C6—C7	1.3453 (15)
N2—C1	1.3600 (12)	C11—C12	1.5234 (14)
N2—C11	1.4521 (12)	C12—C13	1.5180 (14)
N3—C9	1.3101 (12)	C15—C16	1.5145 (13)
N8—C1	1.3934 (12)	C18—C19	1.5074 (13)
N8—C7	1.3804 (11)	C20—C21	1.4086 (12)
N8—C9	1.3835 (11)	C20—C25	1.4081 (12)
N14—C13	1.5009 (12)	C21—C22	1.3880 (14)
N14—C15	1.4928 (11)	C22—C23	1.3812 (14)
N14—C19	1.4959 (12)	C23—C24	1.3906 (15)
N17—C16	1.4626 (11)	C24—C25	1.3819 (15)
N3—N2—C11	120.46 (8)	C6—C7—N8	117.85 (9)
C1—N2—N3	114.18 (8)	N3—C9—N8	111.74 (8)
C1—N2—C11	125.16 (9)	N3—C9—C4	130.33 (9)
C9—N3—N2	103.57 (7)	N8—C9—C4	117.93 (8)
C7—N8—C1	128.23 (8)	N2—C11—C12	113.09 (8)
C7—N8—C9	123.76 (8)	C13—C12—C11	109.91 (8)
C9—N8—C1	107.99 (7)	N14—C13—C12	113.56 (7)
C15—N14—C13	113.13 (7)	N14—C15—C16	111.71 (7)
C15—N14—C19	108.36 (7)	N17—C16—C15	112.38 (7)
C19—N14—C13	109.02 (7)	N17—C18—C19	112.22 (7)
C16—N17—C18	113.04 (7)	N14—C19—C18	111.84 (7)
C20—N17—C16	116.56 (7)	N17—C20—C21	121.73 (8)
C20—N17—C18	115.70 (7)	N17—C20—C25	120.79 (8)
O28—N27—O29	119.74 (8)	C25—C20—C21	117.42 (9)
O28—N27—O30	119.83 (9)	C22—C21—C20	119.57 (8)
O29—N27—O30	120.41 (8)	C21—C22—Cl26	118.50 (7)
O10—C1—N2	129.76 (9)	C23—C22—Cl26	118.36 (8)
O10—C1—N8	127.72 (9)	C23—C22—C21	123.12 (9)
N2—C1—N8	102.51 (7)	C22—C23—C24	117.14 (9)
C5—C4—C9	118.44 (9)	C25—C24—C23	121.46 (9)
C4—C5—C6	121.49 (9)	C24—C25—C20	121.27 (9)
C7—C6—C5	120.52 (9)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N14—H14···O29^i	0.92 (1)	2.35 (1)	3.0162 (11)	130 (1)
N14—H14···O30	0.92 (1)	2.22 (1)	3.0120 (12)	144 (1)

Symmetry code: (i) −x+1, −y+1, −z+1.

(pn180815_uo_traz_1_180814_scn)

Crystal data

1(C19H23ClN5O)·CNS	Z = 4
Mr = 430.95	F(000) = 904
Triclinic, P1	Dx = 1.359 Mg m^−3
a = 12.1482 (2) Å	Cu Kα radiation, λ = 1.54184 Å
b = 13.1848 (2) Å	Cell parameters from 34827 reflections
c = 13.82510 (17) Å	θ = 3.5–78.7°
α = 90.2630 (12)°	µ = 2.73 mm^−1
β = 90.2180 (12)°	T = 160 K
γ = 108.0045 (15)°	Plate, colourless
V = 2105.89 (6) Å^3	0.23 × 0.19 × 0.07 mm

Data collection

XtaLAB Synergy, Dualflex, Pilatus 200K diffractometer	8412 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source	7824 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.032
ω scans	θmax = 78.9°, θmin = 3.2°
Absorption correction: gaussian CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −15→15
Tmin = 0.532, Tmax = 1.000	k = −16→16
52525 measured reflections	l = −16→14

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.057	H-atom parameters constrained
wR(F^2) = 0.136	w = 1/[σ^2(Fo^2) + (0.0411P)^2 + 2.3014P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
8412 reflections	Δρmax = 0.51 e Å^−3
723 parameters	Δρmin = −0.55 e Å^−3
45 restraints

Special details

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl26	0.84874 (7)	0.82750 (5)	−0.05159 (5)	0.0598 (2)
Cl56	0.15284 (16)	−0.32691 (14)	0.45633 (11)	0.0505 (4)	0.492 (3)
Cl57	0.12284 (11)	−0.28589 (15)	0.43681 (12)	0.0468 (4)	0.508 (3)
S29	0.54688 (11)	0.31572 (9)	0.58920 (9)	0.0439 (4)	0.502 (2)
S29B	0.45272 (17)	0.28178 (13)	0.46543 (12)	0.0682 (6)	0.498 (2)
S59	0.4566 (6)	−0.2109 (5)	1.0373 (4)	0.0703 (13)	0.492 (3)
S59B	0.4379 (5)	−0.2233 (4)	1.0463 (3)	0.0476 (6)	0.508 (3)
O10	0.07854 (17)	0.1159 (2)	0.3335 (2)	0.0916 (9)
O40	0.93035 (19)	0.3870 (2)	0.8324 (2)	0.1078 (11)
N2	0.01486 (17)	0.2651 (2)	0.31321 (17)	0.0541 (6)
N3	−0.06980 (17)	0.29125 (18)	0.26031 (16)	0.0466 (5)
N8	−0.07820 (17)	0.12207 (17)	0.23658 (17)	0.0519 (6)
N14	0.38422 (14)	0.41764 (14)	0.24813 (13)	0.0335 (4)
H14	0.4257	0.4440	0.3103	0.040*
N17	0.57940 (15)	0.50147 (14)	0.12163 (13)	0.0327 (4)
N27	0.4571 (4)	0.3732 (4)	0.4197 (3)	0.0527 (11)	0.502 (2)
N27B	0.5511 (4)	0.4393 (4)	0.6014 (3)	0.0497 (11)	0.498 (2)
N32	0.99770 (19)	0.2395 (2)	0.81158 (18)	0.0628 (7)
N33	1.08098 (18)	0.21322 (18)	0.75689 (17)	0.0504 (5)
N38	1.08185 (16)	0.38075 (17)	0.73186 (17)	0.0507 (6)
N44	0.6218 (10)	0.0916 (10)	0.7514 (6)	0.0269 (19)	0.492 (3)
H44	0.5832	0.0586	0.8124	0.032*	0.492 (3)
N44B	0.6613 (3)	0.0089 (3)	0.7380 (3)	0.0304 (8)	0.508 (3)
H44B	0.6215	−0.0334	0.7948	0.036*	0.508 (3)
N47	0.4273 (5)	0.0075 (5)	0.6210 (5)	0.0306 (12)	0.492 (3)
N47B	0.4527 (5)	−0.0205 (5)	0.6257 (4)	0.0272 (11)	0.508 (3)
N57	0.5556 (4)	−0.0582 (4)	0.8993 (3)	0.0451 (10)	0.492 (3)
N57B	0.5660 (4)	−0.1156 (4)	0.8926 (3)	0.0488 (11)	0.508 (3)
C1	0.0143 (2)	0.1625 (3)	0.3000 (2)	0.0632 (9)
C4	−0.2187 (2)	0.1784 (2)	0.1482 (2)	0.0518 (6)
H4	−0.2530	0.2314	0.1304	0.062*
C5	−0.2587 (3)	0.0792 (2)	0.1108 (2)	0.0609 (7)
H5	−0.3210	0.0632	0.0658	0.073*
C6	−0.2106 (3)	−0.0020 (3)	0.1365 (3)	0.0682 (9)
H6	−0.2416	−0.0716	0.1098	0.082*
C7	−0.1215 (3)	0.0197 (2)	0.1985 (3)	0.0693 (10)
H7	−0.0883	−0.0341	0.2162	0.083*
C9	−0.1242 (2)	0.2027 (2)	0.21484 (18)	0.0423 (6)
C11	0.0930 (2)	0.3432 (3)	0.3758 (2)	0.0692 (9)
H11A	0.1229	0.3057	0.4264	0.083*
H11B	0.0496	0.3859	0.4083	0.083*
C12	0.1945 (2)	0.4178 (3)	0.3217 (2)	0.0569 (7)
H12A	0.1658	0.4586	0.2732	0.068*
H12B	0.2456	0.4691	0.3677	0.068*
C13	0.2622 (2)	0.3538 (2)	0.27163 (19)	0.0518 (7)
H13A	0.2637	0.2937	0.3137	0.062*
H13B	0.2216	0.3233	0.2110	0.062*
C15	0.3948 (2)	0.5113 (2)	0.18572 (18)	0.0467 (6)
H15A	0.3582	0.5598	0.2179	0.056*
H15B	0.3538	0.4873	0.1237	0.056*
C16	0.5206 (2)	0.57030 (19)	0.1662 (2)	0.0476 (6)
H16A	0.5256	0.6312	0.1230	0.057*
H16B	0.5598	0.5991	0.2278	0.057*
C18	0.5688 (2)	0.40778 (18)	0.18042 (18)	0.0401 (5)
H18A	0.6101	0.4300	0.2426	0.048*
H18B	0.6053	0.3603	0.1465	0.048*
C19	0.4437 (2)	0.34787 (19)	0.1999 (2)	0.0488 (6)
H19A	0.4039	0.3206	0.1381	0.059*
H19B	0.4391	0.2859	0.2417	0.059*
C20	0.68396 (17)	0.54862 (17)	0.07376 (15)	0.0314 (4)
C21	0.71671 (19)	0.65540 (17)	0.04478 (15)	0.0346 (4)
H21	0.6717	0.6998	0.0628	0.041*
C22	0.8155 (2)	0.69575 (18)	−0.01057 (16)	0.0406 (5)
C23	0.8853 (2)	0.6363 (2)	−0.03819 (18)	0.0462 (6)
H23	0.9522	0.6661	−0.0764	0.055*
C24	0.85426 (19)	0.5316 (2)	−0.00830 (18)	0.0450 (6)
H24	0.9010	0.4886	−0.0259	0.054*
C25	0.75637 (19)	0.48817 (19)	0.04681 (17)	0.0389 (5)
H25	0.7376	0.4160	0.0669	0.047*
C28	0.4950 (4)	0.3500 (3)	0.4913 (4)	0.0313 (10)	0.502 (2)
C28B	0.5126 (4)	0.3751 (4)	0.5448 (4)	0.0352 (10)	0.498 (2)
C31	0.9939 (2)	0.3411 (3)	0.7979 (2)	0.0676 (10)
C34	1.2208 (2)	0.3262 (2)	0.6408 (2)	0.0522 (7)
H34	1.2568	0.2744	0.6232	0.063*
C35	1.2559 (3)	0.4243 (3)	0.6008 (2)	0.0621 (7)
H35	1.3165	0.4403	0.5546	0.075*
C36	1.2056 (3)	0.5027 (3)	0.6256 (3)	0.0700 (9)
H36	1.2321	0.5711	0.5965	0.084*
C37	1.1204 (3)	0.4818 (2)	0.6901 (3)	0.0675 (10)
H37	1.0863	0.5350	0.7075	0.081*
C39	1.12930 (19)	0.3012 (2)	0.70968 (19)	0.0427 (6)
C41	0.9147 (8)	0.1780 (8)	0.8740 (7)	0.067 (3)	0.492 (3)
H41A	0.8810	0.2249	0.9121	0.080*	0.492 (3)
H41B	0.9515	0.1406	0.9197	0.080*	0.492 (3)
C41B	0.9333 (6)	0.1492 (7)	0.8816 (6)	0.0546 (14)	0.508 (3)
H41C	0.9714	0.0928	0.8798	0.066*	0.508 (3)
H41D	0.9412	0.1785	0.9482	0.066*	0.508 (3)
C42	0.8179 (5)	0.0957 (5)	0.8176 (5)	0.0403 (15)	0.492 (3)
H42A	0.7722	0.0389	0.8610	0.048*	0.492 (3)
H42B	0.8505	0.0627	0.7650	0.048*	0.492 (3)
C42B	0.8069 (6)	0.0997 (7)	0.8588 (5)	0.0558 (19)	0.508 (3)
H42C	0.7679	0.1554	0.8612	0.067*	0.508 (3)
H42D	0.7713	0.0457	0.9084	0.067*	0.508 (3)
C43	0.7425 (3)	0.1600 (3)	0.7760 (3)	0.0315 (9)	0.492 (3)
H43A	0.7386	0.2148	0.8239	0.038*	0.492 (3)
H43B	0.7796	0.1972	0.7170	0.038*	0.492 (3)
C43B	0.7889 (4)	0.0476 (4)	0.7603 (3)	0.0366 (10)	0.508 (3)
H43C	0.8298	0.0996	0.7108	0.044*	0.508 (3)
H43D	0.8206	−0.0131	0.7593	0.044*	0.508 (3)
C45	0.6173 (4)	0.0041 (3)	0.6805 (4)	0.0305 (10)	0.492 (3)
H45A	0.6575	−0.0441	0.7082	0.037*	0.492 (3)
H45B	0.6579	0.0351	0.6205	0.037*	0.492 (3)
C45B	0.6346 (3)	−0.0631 (3)	0.6516 (3)	0.0296 (9)	0.508 (3)
H45C	0.6654	−0.1235	0.6619	0.035*	0.508 (3)
H45D	0.6731	−0.0233	0.5941	0.035*	0.508 (3)
C46	0.4928 (4)	−0.0593 (5)	0.6566 (4)	0.0335 (10)	0.492 (3)
H46A	0.4921	−0.1141	0.6072	0.040*	0.492 (3)
H46B	0.4551	−0.0966	0.7154	0.040*	0.492 (3)
C46B	0.5048 (4)	−0.1058 (4)	0.6333 (4)	0.0308 (10)	0.508 (3)
H46C	0.4902	−0.1481	0.5726	0.037*	0.508 (3)
H46D	0.4679	−0.1537	0.6868	0.037*	0.508 (3)
C48	0.4317 (4)	0.0940 (4)	0.6890 (4)	0.0382 (11)	0.492 (3)
H48A	0.3931	0.0637	0.7500	0.046*	0.492 (3)
H48B	0.3892	0.1403	0.6613	0.046*	0.492 (3)
C48B	0.4813 (4)	0.0520 (3)	0.7087 (3)	0.0333 (10)	0.508 (3)
H48C	0.4460	0.0133	0.7677	0.040*	0.508 (3)
H48D	0.4486	0.1112	0.6986	0.040*	0.508 (3)
C49	0.5549 (4)	0.1598 (3)	0.7104 (3)	0.0348 (10)	0.492 (3)
H49A	0.5922	0.1937	0.6501	0.042*	0.492 (3)
H49B	0.5556	0.2171	0.7571	0.042*	0.492 (3)
C49B	0.6102 (12)	0.0966 (12)	0.7226 (8)	0.033 (2)	0.508 (3)
H49C	0.6453	0.1380	0.6648	0.040*	0.508 (3)
H49D	0.6275	0.1454	0.7791	0.040*	0.508 (3)
C50	0.3260 (15)	−0.0381 (12)	0.5756 (14)	0.025 (2)	0.492 (3)
C50B	0.3353 (18)	−0.0522 (14)	0.5885 (15)	0.036 (3)	0.508 (3)
C51	0.2921 (14)	−0.1535 (14)	0.5456 (14)	0.023 (2)	0.492 (3)
H51	0.3404	−0.1965	0.5582	0.027*	0.492 (3)
C51B	0.2830 (16)	−0.1418 (16)	0.5448 (17)	0.037 (4)	0.508 (3)
H51B	0.3183	−0.1968	0.5483	0.044*	0.508 (3)
C52	0.1847 (15)	−0.1943 (8)	0.4976 (13)	0.034 (2)	0.492 (3)
C52B	0.1822 (14)	−0.1631 (8)	0.4944 (12)	0.036 (2)	0.508 (3)
C53	0.1174 (6)	−0.1358 (7)	0.4657 (5)	0.0413 (15)	0.492 (3)
H53	0.0509	−0.1669	0.4265	0.050*	0.492 (3)
C53B	0.1194 (6)	−0.0927 (8)	0.4991 (6)	0.0437 (16)	0.508 (3)
H53B	0.0447	−0.1089	0.4704	0.052*	0.508 (3)
C54	0.1492 (6)	−0.0291 (7)	0.4922 (5)	0.0429 (14)	0.492 (3)
H54	0.1019	0.0130	0.4733	0.051*	0.492 (3)
C54B	0.1689 (5)	0.0025 (5)	0.5469 (5)	0.0442 (12)	0.508 (3)
H54B	0.1283	0.0536	0.5498	0.053*	0.508 (3)
C55	0.2485 (6)	0.0171 (5)	0.5458 (5)	0.0383 (14)	0.492 (3)
H55	0.2658	0.0901	0.5636	0.046*	0.492 (3)
C55B	0.2766 (5)	0.0255 (4)	0.5911 (5)	0.0381 (13)	0.508 (3)
H55B	0.3106	0.0921	0.6225	0.046*	0.508 (3)
C58	0.5140 (7)	−0.1210 (4)	0.9552 (4)	0.0325 (13)	0.492 (3)
C58B	0.5161 (5)	−0.1566 (4)	0.9574 (4)	0.0268 (10)	0.508 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl26	0.0730 (4)	0.0428 (3)	0.0479 (4)	−0.0052 (3)	0.0060 (3)	−0.0007 (3)
Cl56	0.0509 (8)	0.0406 (8)	0.0477 (8)	−0.0037 (6)	−0.0125 (6)	0.0064 (6)
Cl57	0.0331 (6)	0.0522 (9)	0.0459 (8)	−0.0001 (5)	−0.0052 (5)	−0.0013 (6)
S29	0.0567 (7)	0.0456 (7)	0.0346 (7)	0.0237 (5)	−0.0122 (5)	−0.0005 (5)
S29B	0.1058 (13)	0.0485 (9)	0.0581 (10)	0.0360 (9)	−0.0349 (9)	−0.0269 (7)
S59	0.082 (3)	0.0468 (14)	0.088 (2)	0.0278 (15)	0.0446 (14)	0.0378 (12)
S59B	0.0570 (13)	0.0381 (12)	0.0496 (12)	0.0170 (9)	0.0206 (10)	0.0112 (10)
O10	0.0431 (11)	0.1097 (19)	0.134 (2)	0.0395 (12)	0.0188 (12)	0.0811 (17)
O40	0.0476 (12)	0.133 (2)	0.144 (2)	0.0311 (13)	−0.0014 (14)	−0.098 (2)
N2	0.0322 (10)	0.0763 (15)	0.0563 (14)	0.0201 (10)	0.0113 (10)	0.0293 (12)
N3	0.0393 (10)	0.0593 (13)	0.0496 (13)	0.0273 (10)	0.0106 (9)	0.0151 (10)
N8	0.0368 (10)	0.0548 (12)	0.0734 (15)	0.0271 (9)	0.0256 (10)	0.0357 (11)
N14	0.0282 (8)	0.0439 (10)	0.0260 (9)	0.0079 (7)	−0.0014 (7)	−0.0053 (7)
N17	0.0327 (9)	0.0399 (9)	0.0307 (10)	0.0185 (7)	0.0042 (7)	0.0034 (7)
N27	0.067 (3)	0.057 (3)	0.039 (3)	0.027 (2)	−0.005 (2)	0.008 (2)
N27B	0.051 (2)	0.052 (2)	0.044 (3)	0.013 (2)	−0.012 (2)	−0.014 (2)
N32	0.0369 (11)	0.0803 (16)	0.0573 (15)	−0.0016 (10)	0.0008 (10)	−0.0322 (12)
N33	0.0392 (10)	0.0568 (13)	0.0549 (14)	0.0147 (10)	−0.0060 (10)	−0.0183 (10)
N38	0.0323 (10)	0.0548 (12)	0.0694 (15)	0.0204 (9)	−0.0163 (10)	−0.0339 (11)
N44	0.025 (2)	0.034 (2)	0.021 (5)	0.0085 (18)	0.000 (3)	0.002 (3)
N44B	0.0293 (17)	0.0371 (18)	0.022 (2)	0.0060 (14)	−0.0009 (16)	0.0016 (13)
N47	0.026 (3)	0.036 (3)	0.034 (2)	0.016 (2)	−0.004 (2)	−0.003 (2)
N47B	0.029 (3)	0.031 (3)	0.027 (2)	0.0167 (18)	−0.002 (2)	−0.001 (2)
N57	0.049 (2)	0.038 (2)	0.047 (2)	0.0117 (18)	0.0106 (17)	0.0098 (17)
N57B	0.052 (2)	0.050 (3)	0.0418 (19)	0.012 (2)	0.0110 (17)	0.0127 (18)
C1	0.0345 (12)	0.080 (2)	0.082 (2)	0.0278 (13)	0.0226 (13)	0.0530 (17)
C4	0.0549 (15)	0.0631 (16)	0.0479 (16)	0.0336 (13)	0.0075 (12)	0.0127 (12)
C5	0.0731 (19)	0.0684 (18)	0.0457 (16)	0.0283 (15)	0.0160 (14)	0.0033 (13)
C6	0.075 (2)	0.0597 (17)	0.075 (2)	0.0276 (16)	0.0414 (18)	0.0047 (15)
C7	0.0629 (18)	0.0538 (16)	0.104 (3)	0.0359 (14)	0.0516 (19)	0.0368 (17)
C9	0.0403 (12)	0.0511 (13)	0.0451 (14)	0.0276 (11)	0.0171 (10)	0.0189 (11)
C11	0.0432 (14)	0.120 (3)	0.0437 (17)	0.0235 (17)	0.0135 (13)	0.0132 (16)
C12	0.0341 (12)	0.094 (2)	0.0396 (15)	0.0152 (13)	0.0051 (11)	−0.0028 (13)
C13	0.0299 (11)	0.0734 (17)	0.0399 (15)	−0.0016 (11)	0.0029 (10)	−0.0149 (12)
C15	0.0415 (12)	0.0768 (17)	0.0337 (13)	0.0354 (12)	0.0079 (10)	0.0140 (11)
C16	0.0526 (14)	0.0439 (12)	0.0566 (16)	0.0292 (11)	0.0262 (12)	0.0165 (11)
C18	0.0408 (12)	0.0402 (12)	0.0442 (14)	0.0197 (10)	0.0076 (10)	0.0056 (9)
C19	0.0499 (14)	0.0390 (12)	0.0536 (16)	0.0080 (10)	0.0172 (12)	−0.0075 (10)
C20	0.0314 (10)	0.0408 (11)	0.0235 (11)	0.0134 (8)	−0.0021 (8)	−0.0044 (8)
C21	0.0371 (11)	0.0382 (11)	0.0275 (11)	0.0103 (9)	−0.0006 (9)	−0.0079 (8)
C22	0.0433 (12)	0.0423 (12)	0.0275 (12)	0.0004 (10)	−0.0006 (9)	−0.0076 (9)
C23	0.0333 (11)	0.0616 (15)	0.0355 (13)	0.0029 (10)	0.0055 (10)	−0.0113 (11)
C24	0.0330 (11)	0.0609 (15)	0.0441 (14)	0.0191 (10)	0.0028 (10)	−0.0118 (11)
C25	0.0355 (11)	0.0436 (12)	0.0417 (13)	0.0183 (9)	0.0020 (9)	−0.0011 (9)
C28	0.030 (2)	0.025 (3)	0.035 (3)	0.0031 (17)	0.001 (2)	−0.004 (2)
C28B	0.045 (3)	0.033 (2)	0.030 (3)	0.015 (2)	−0.004 (2)	−0.003 (2)
C31	0.0350 (13)	0.083 (2)	0.082 (2)	0.0158 (13)	−0.0099 (13)	−0.0582 (18)
C34	0.0447 (13)	0.0664 (17)	0.0542 (17)	0.0303 (13)	−0.0108 (12)	−0.0177 (13)
C35	0.0564 (16)	0.074 (2)	0.0541 (19)	0.0182 (15)	−0.0136 (14)	−0.0052 (14)
C36	0.0606 (19)	0.0644 (19)	0.085 (3)	0.0195 (15)	−0.0322 (18)	−0.0043 (16)
C37	0.0611 (18)	0.0494 (15)	0.100 (3)	0.0303 (14)	−0.0482 (18)	−0.0329 (16)
C39	0.0346 (11)	0.0495 (13)	0.0490 (15)	0.0209 (10)	−0.0150 (10)	−0.0226 (11)
C41	0.072 (6)	0.067 (5)	0.055 (5)	0.012 (4)	−0.014 (4)	0.008 (4)
C41B	0.027 (2)	0.080 (3)	0.048 (3)	0.0038 (19)	0.0023 (18)	−0.036 (2)
C42	0.033 (3)	0.042 (3)	0.044 (5)	0.008 (2)	0.007 (3)	0.000 (3)
C42B	0.031 (2)	0.081 (4)	0.045 (4)	0.0029 (19)	−0.001 (2)	−0.021 (3)
C43	0.0278 (19)	0.034 (2)	0.030 (2)	0.0056 (16)	−0.0005 (16)	0.0015 (16)
C43B	0.031 (2)	0.044 (2)	0.029 (3)	0.0035 (18)	−0.0014 (18)	0.000 (2)
C45	0.030 (2)	0.035 (2)	0.028 (3)	0.0129 (17)	−0.0006 (19)	−0.0013 (17)
C45B	0.033 (2)	0.032 (2)	0.027 (2)	0.0150 (16)	−0.0041 (16)	−0.0013 (15)
C46	0.032 (2)	0.029 (3)	0.041 (3)	0.012 (2)	−0.005 (2)	−0.006 (2)
C46B	0.031 (2)	0.027 (2)	0.036 (3)	0.0113 (18)	−0.0097 (18)	−0.0028 (19)
C48	0.036 (2)	0.043 (2)	0.041 (3)	0.019 (2)	−0.0021 (19)	−0.0090 (19)
C48B	0.036 (2)	0.038 (2)	0.028 (2)	0.0153 (19)	0.0014 (17)	−0.0049 (16)
C49	0.038 (2)	0.037 (2)	0.034 (3)	0.0173 (18)	−0.0028 (18)	−0.0022 (17)
C49B	0.038 (4)	0.034 (3)	0.026 (6)	0.010 (2)	0.000 (4)	−0.005 (4)
C50	0.027 (3)	0.026 (4)	0.021 (5)	0.005 (3)	0.004 (3)	0.006 (3)
C50B	0.048 (5)	0.038 (5)	0.030 (6)	0.026 (3)	0.015 (4)	0.016 (3)
C51	0.018 (3)	0.026 (3)	0.021 (4)	0.003 (4)	0.000 (3)	0.005 (3)
C51B	0.037 (5)	0.042 (6)	0.040 (5)	0.025 (4)	0.002 (3)	0.007 (4)
C52	0.029 (3)	0.034 (5)	0.030 (3)	−0.005 (4)	0.002 (2)	0.020 (4)
C52B	0.034 (3)	0.035 (5)	0.030 (3)	−0.003 (5)	0.002 (2)	0.016 (5)
C53	0.028 (3)	0.066 (5)	0.028 (4)	0.012 (3)	−0.002 (3)	0.005 (3)
C53B	0.023 (3)	0.070 (6)	0.040 (4)	0.017 (3)	0.004 (3)	0.009 (4)
C54	0.032 (3)	0.066 (4)	0.037 (4)	0.027 (3)	−0.002 (3)	0.000 (4)
C54B	0.034 (3)	0.061 (3)	0.047 (4)	0.027 (2)	0.005 (3)	0.004 (3)
C55	0.036 (3)	0.049 (3)	0.036 (4)	0.022 (2)	−0.006 (3)	−0.003 (3)
C55B	0.035 (3)	0.049 (3)	0.036 (4)	0.022 (2)	0.002 (2)	0.000 (2)
C58	0.041 (3)	0.021 (2)	0.0343 (19)	0.009 (2)	0.0059 (17)	−0.0052 (18)
C58B	0.0316 (19)	0.019 (2)	0.0296 (17)	0.008 (2)	−0.0013 (13)	−0.0029 (17)

Geometric parameters (Å, º)

Cl26—C22	1.755 (2)	N47B—C48B	1.460 (7)
Cl56—C52	1.761 (13)	N47B—C50B	1.45 (2)
Cl57—C52B	1.743 (13)	N57—C58	1.134 (6)
S29—C28	1.615 (6)	N57B—C58B	1.127 (5)
S29B—C28B	1.636 (6)	C4—C5	1.347 (4)
S59—C58	1.6396 (10)	C4—C9	1.425 (4)
S59B—C58B	1.6388 (10)	C5—C6	1.414 (4)
O10—C1	1.223 (3)	C6—C7	1.338 (5)
O40—C31	1.216 (3)	C11—C12	1.520 (4)
N2—N3	1.388 (3)	C12—C13	1.515 (4)
N2—C1	1.362 (4)	C15—C16	1.510 (3)
N2—C11	1.445 (4)	C18—C19	1.506 (3)
N3—C9	1.307 (3)	C20—C21	1.400 (3)
N8—C1	1.391 (4)	C20—C25	1.408 (3)
N8—C7	1.389 (4)	C21—C22	1.388 (3)
N8—C9	1.379 (3)	C22—C23	1.374 (3)
N14—C13	1.498 (3)	C23—C24	1.379 (4)
N14—C15	1.482 (3)	C24—C25	1.383 (3)
N14—C19	1.491 (3)	C34—C35	1.352 (4)
N17—C16	1.454 (3)	C34—C39	1.426 (4)
N17—C18	1.454 (3)	C35—C36	1.396 (5)
N17—C20	1.400 (3)	C36—C37	1.332 (5)
N27—C28	1.171 (7)	C41—C42	1.538 (12)
N27B—C28B	1.137 (7)	C41B—C42B	1.503 (10)
N32—N33	1.391 (3)	C42—C43	1.538 (8)
N32—C31	1.368 (4)	C42B—C43B	1.507 (7)
N32—C41	1.389 (9)	C45—C46	1.520 (6)
N32—C41B	1.551 (8)	C45B—C46B	1.521 (6)
N33—C39	1.306 (4)	C48—C49	1.508 (6)
N38—C31	1.384 (4)	C48B—C49B	1.505 (15)
N38—C37	1.397 (4)	C50—C51	1.50 (3)
N38—C39	1.378 (3)	C50—C55	1.419 (16)
N44—C43	1.502 (12)	C50B—C51B	1.30 (3)
N44—C45	1.499 (13)	C50B—C55B	1.416 (16)
N44—C49	1.497 (11)	C51—C52	1.41 (2)
N44B—C43B	1.504 (6)	C51B—C52B	1.36 (2)
N44B—C45B	1.493 (5)	C52—C53	1.360 (14)
N44B—C49B	1.488 (14)	C52B—C53B	1.374 (15)
N47—C46	1.444 (7)	C53—C54	1.387 (10)
N47—C48	1.464 (7)	C53B—C54B	1.377 (10)
N47—C50	1.343 (18)	C54—C55	1.381 (9)
N47B—C46B	1.455 (6)	C54B—C55B	1.388 (8)
N3—N2—C11	120.6 (2)	C21—C22—Cl26	117.98 (19)
C1—N2—N3	113.7 (2)	C23—C22—Cl26	118.68 (18)
C1—N2—C11	125.8 (2)	C23—C22—C21	123.3 (2)
C9—N3—N2	103.7 (2)	C22—C23—C24	117.4 (2)
C7—N8—C1	128.7 (2)	C23—C24—C25	121.2 (2)
C9—N8—C1	108.3 (2)	C24—C25—C20	121.4 (2)
C9—N8—C7	123.0 (3)	N27—C28—S29	178.9 (5)
C15—N14—C13	114.51 (19)	N27B—C28B—S29B	177.9 (5)
C15—N14—C19	108.55 (18)	O40—C31—N32	130.5 (4)
C19—N14—C13	109.71 (18)	O40—C31—N38	127.4 (4)
C16—N17—C18	111.13 (17)	N32—C31—N38	102.0 (2)
C20—N17—C16	118.60 (18)	C35—C34—C39	119.5 (2)
C20—N17—C18	118.46 (17)	C34—C35—C36	121.8 (3)
N33—N32—C41B	112.6 (4)	C37—C36—C35	120.0 (3)
C31—N32—N33	114.4 (2)	C36—C37—N38	119.3 (3)
C31—N32—C41	115.0 (5)	N33—C39—N38	112.7 (2)
C31—N32—C41B	132.8 (4)	N33—C39—C34	130.5 (2)
C41—N32—N33	130.5 (5)	N38—C39—C34	116.8 (2)
C39—N33—N32	102.5 (2)	N32—C41—C42	110.9 (7)
C31—N38—C37	129.1 (2)	C42B—C41B—N32	114.2 (6)
C39—N38—C31	108.4 (2)	C41—C42—C43	104.7 (5)
C39—N38—C37	122.5 (3)	C41B—C42B—C43B	111.5 (6)
C45—N44—C43	113.6 (8)	N44—C43—C42	112.9 (5)
C49—N44—C43	109.5 (8)	N44B—C43B—C42B	108.9 (4)
C49—N44—C45	108.6 (6)	N44—C45—C46	110.7 (6)
C45B—N44B—C43B	111.9 (3)	N44B—C45B—C46B	111.1 (4)
C49B—N44B—C43B	113.5 (6)	N47—C46—C45	112.3 (5)
C49B—N44B—C45B	108.5 (6)	N47B—C46B—C45B	112.0 (4)
C46—N47—C48	111.3 (6)	N47—C48—C49	111.1 (4)
C50—N47—C46	119.1 (8)	N47B—C48B—C49B	111.1 (7)
C50—N47—C48	116.8 (9)	N44—C49—C48	110.7 (6)
C46B—N47B—C48B	112.1 (4)	N44B—C49B—C48B	110.4 (10)
C50B—N47B—C46B	115.4 (8)	N47—C50—C51	120.3 (13)
C50B—N47B—C48B	118.4 (10)	N47—C50—C55	124.5 (12)
O10—C1—N2	129.9 (3)	C55—C50—C51	115.0 (13)
O10—C1—N8	127.5 (3)	C51B—C50B—N47B	125.6 (16)
N2—C1—N8	102.5 (2)	C51B—C50B—C55B	117.0 (17)
C5—C4—C9	119.0 (3)	C55B—C50B—N47B	117.0 (14)
C4—C5—C6	122.0 (3)	C52—C51—C50	116.3 (16)
C7—C6—C5	119.7 (3)	C50B—C51B—C52B	125.2 (18)
C6—C7—N8	118.9 (3)	C51—C52—Cl56	114.9 (11)
N3—C9—N8	111.7 (2)	C53—C52—Cl56	118.3 (11)
N3—C9—C4	131.0 (2)	C53—C52—C51	125.6 (12)
N8—C9—C4	117.3 (2)	C51B—C52B—Cl57	120.6 (12)
N2—C11—C12	112.9 (2)	C51B—C52B—C53B	119.4 (14)
C13—C12—C11	109.8 (3)	C53B—C52B—Cl57	119.5 (11)
N14—C13—C12	113.7 (2)	C52—C53—C54	117.6 (8)
N14—C15—C16	110.57 (18)	C52B—C53B—C54B	117.4 (8)
N17—C16—C15	111.7 (2)	C55—C54—C53	121.1 (6)
N17—C18—C19	111.09 (19)	C53B—C54B—C55B	121.5 (5)
N14—C19—C18	111.22 (19)	C54—C55—C50	123.7 (8)
N17—C20—C21	121.52 (18)	C54B—C55B—C50B	118.9 (10)
N17—C20—C25	121.00 (19)	N57—C58—S59	178.7 (8)
C21—C20—C25	117.32 (19)	N57B—C58B—S59B	175.7 (6)
C22—C21—C20	119.4 (2)

(pn180817_uo_trh_1_180814_b1_bf4)

Crystal data

C19H23ClN5O·BF4	F(000) = 952
Mr = 459.68	Dx = 1.468 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
a = 12.46473 (13) Å	Cell parameters from 36021 reflections
b = 12.98315 (16) Å	θ = 3.7–78.6°
c = 13.42014 (13) Å	µ = 2.15 mm^−1
β = 106.7648 (11)°	T = 160 K
V = 2079.49 (4) Å^3	Plate, colourless
Z = 4	0.19 × 0.17 × 0.02 mm

Data collection

XtaLAB Synergy, Dualflex, Pilatus 200K diffractometer	4315 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source	4165 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.029
ω scans	θmax = 78.8°, θmin = 3.7°
Absorption correction: gaussian CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −15→15
Tmin = 0.531, Tmax = 1.000	k = −14→13
48534 measured reflections	l = −17→17

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.042	H-atom parameters constrained
wR(F^2) = 0.104	w = 1/[σ^2(Fo^2) + (0.0247P)^2 + 2.2045P] where P = (Fo^2 + 2Fc^2)/3
S = 1.16	(Δ/σ)max = 0.001
4315 reflections	Δρmax = 0.33 e Å^−3
293 parameters	Δρmin = −0.31 e Å^−3
0 restraints

Special details

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl25	0.85574 (4)	1.05286 (4)	0.81194 (4)	0.03444 (14)
F31	0.56726 (12)	0.46652 (11)	0.61432 (13)	0.0505 (4)
O26	0.09252 (12)	0.63897 (13)	0.16171 (11)	0.0375 (4)
N3	−0.06166 (12)	0.74773 (12)	0.14934 (11)	0.0225 (3)
N9	−0.06722 (13)	0.74091 (13)	0.31384 (12)	0.0250 (3)
N13	0.57458 (12)	0.87012 (12)	0.50597 (11)	0.0234 (3)
N16	0.38170 (12)	0.73589 (12)	0.43954 (11)	0.0212 (3)
H16	0.4180	0.6712	0.4736	0.025*
F29	0.4050 (2)	0.44050 (16)	0.6531 (3)	0.0541 (6)	0.910 (8)
N1	0.01837 (12)	0.68007 (13)	0.29821 (12)	0.0248 (3)
F27	0.4500 (3)	0.6010 (2)	0.6109 (2)	0.0604 (8)	0.910 (8)
F30	0.54252 (18)	0.5304 (2)	0.76267 (15)	0.0631 (8)	0.910 (8)
C8	−0.11390 (15)	0.78077 (15)	0.22159 (13)	0.0231 (4)
C20	0.71654 (15)	0.95133 (14)	0.65045 (14)	0.0235 (4)
H20	0.6755	0.9344	0.6978	0.028*
C2	0.02605 (15)	0.68205 (15)	0.19910 (14)	0.0253 (4)
C19	0.67851 (14)	0.91925 (14)	0.54624 (14)	0.0222 (4)
C12	0.26288 (15)	0.71104 (15)	0.37971 (14)	0.0257 (4)
H12A	0.2634	0.6571	0.3277	0.031*
H12B	0.2277	0.7733	0.3414	0.031*
C14	0.56598 (15)	0.79118 (15)	0.42613 (14)	0.0248 (4)
H14A	0.6000	0.7263	0.4594	0.030*
H14B	0.6077	0.8137	0.3774	0.030*
C18	0.51288 (15)	0.83978 (16)	0.57890 (14)	0.0268 (4)
H18A	0.5159	0.8963	0.6291	0.032*
H18B	0.5488	0.7784	0.6185	0.032*
C4	−0.09293 (16)	0.77886 (16)	0.04663 (14)	0.0277 (4)
H4	−0.0552	0.7536	−0.0006	0.033*
C17	0.39154 (15)	0.81541 (15)	0.52239 (14)	0.0247 (4)
H17A	0.3537	0.7902	0.5732	0.030*
H17B	0.3531	0.8792	0.4905	0.030*
C24	0.74436 (16)	0.94448 (15)	0.48051 (15)	0.0272 (4)
H24	0.7207	0.9233	0.4098	0.033*
C15	0.44479 (15)	0.77242 (15)	0.36659 (14)	0.0249 (4)
H15A	0.4109	0.8369	0.3323	0.030*
H15B	0.4402	0.7200	0.3120	0.030*
C23	0.84282 (16)	0.99947 (16)	0.51686 (16)	0.0296 (4)
H23	0.8860	1.0147	0.4708	0.035*
C22	0.88003 (16)	1.03293 (15)	0.61944 (16)	0.0288 (4)
H22	0.9474	1.0712	0.6444	0.035*
C7	−0.20488 (16)	0.85090 (16)	0.18771 (15)	0.0286 (4)
H7	−0.2436	0.8752	0.2345	0.034*
C5	−0.17808 (17)	0.84582 (17)	0.01533 (15)	0.0313 (4)
H5	−0.2006	0.8692	−0.0547	0.038*
C21	0.81480 (15)	1.00811 (15)	0.68340 (14)	0.0252 (4)
B28	0.49146 (18)	0.51001 (17)	0.65970 (16)	0.0249 (4)
C6	−0.23499 (16)	0.88219 (16)	0.08699 (16)	0.0311 (4)
H6	−0.2953	0.9294	0.0635	0.037*
C10	0.08810 (16)	0.61766 (16)	0.38200 (15)	0.0297 (4)
H10A	0.1121	0.5552	0.3518	0.036*
H10B	0.0428	0.5951	0.4277	0.036*
C11	0.19198 (16)	0.67406 (16)	0.44786 (15)	0.0281 (4)
H11A	0.1689	0.7338	0.4828	0.034*
H11B	0.2368	0.6272	0.5023	0.034*
F1	0.5521 (17)	0.579 (2)	0.733 (2)	0.058 (7)*	0.090 (8)
F2	0.4382 (16)	0.4421 (14)	0.6877 (13)	0.022 (4)*	0.090 (8)
F3	0.4257 (19)	0.568 (2)	0.579 (2)	0.051 (6)*	0.090 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl25	0.0346 (3)	0.0345 (3)	0.0281 (2)	−0.00614 (19)	−0.00078 (18)	−0.00437 (19)
F31	0.0529 (8)	0.0334 (8)	0.0773 (10)	0.0060 (6)	0.0379 (8)	0.0002 (7)
O26	0.0270 (7)	0.0496 (10)	0.0363 (8)	0.0050 (6)	0.0094 (6)	−0.0129 (7)
N3	0.0193 (7)	0.0281 (9)	0.0195 (7)	−0.0040 (6)	0.0045 (5)	−0.0039 (6)
N9	0.0225 (7)	0.0295 (9)	0.0230 (7)	−0.0004 (6)	0.0063 (6)	−0.0019 (6)
N13	0.0233 (7)	0.0243 (8)	0.0229 (7)	−0.0023 (6)	0.0072 (6)	−0.0040 (6)
N16	0.0201 (7)	0.0181 (8)	0.0221 (7)	0.0014 (6)	0.0012 (6)	0.0010 (6)
F29	0.0432 (12)	0.0540 (11)	0.0698 (16)	−0.0224 (9)	0.0237 (12)	−0.0255 (10)
N1	0.0212 (7)	0.0275 (9)	0.0235 (7)	0.0008 (6)	0.0031 (6)	−0.0007 (6)
F27	0.0923 (16)	0.0408 (14)	0.0503 (13)	0.0342 (12)	0.0242 (12)	0.0217 (10)
F30	0.0824 (14)	0.0664 (17)	0.0260 (9)	−0.0103 (11)	−0.0072 (8)	−0.0087 (9)
C8	0.0231 (8)	0.0254 (10)	0.0210 (8)	−0.0051 (7)	0.0070 (7)	−0.0054 (7)
C20	0.0235 (8)	0.0218 (10)	0.0245 (9)	0.0005 (7)	0.0056 (7)	0.0019 (7)
C2	0.0204 (8)	0.0283 (10)	0.0257 (9)	−0.0031 (7)	0.0043 (7)	−0.0064 (7)
C19	0.0217 (8)	0.0178 (9)	0.0258 (9)	0.0031 (7)	0.0048 (7)	0.0016 (7)
C12	0.0208 (8)	0.0274 (10)	0.0239 (9)	0.0011 (7)	−0.0017 (7)	0.0012 (7)
C14	0.0241 (9)	0.0243 (10)	0.0253 (9)	0.0007 (7)	0.0057 (7)	−0.0045 (7)
C18	0.0255 (9)	0.0312 (11)	0.0232 (9)	−0.0059 (7)	0.0064 (7)	−0.0041 (7)
C4	0.0269 (9)	0.0364 (11)	0.0193 (8)	−0.0104 (8)	0.0058 (7)	−0.0038 (7)
C17	0.0242 (9)	0.0233 (10)	0.0263 (9)	−0.0005 (7)	0.0070 (7)	−0.0035 (7)
C24	0.0284 (9)	0.0263 (10)	0.0269 (9)	−0.0002 (7)	0.0081 (7)	−0.0005 (7)
C15	0.0266 (9)	0.0260 (10)	0.0208 (8)	−0.0003 (7)	0.0045 (7)	−0.0003 (7)
C23	0.0285 (9)	0.0275 (11)	0.0354 (10)	0.0016 (8)	0.0136 (8)	0.0033 (8)
C22	0.0227 (9)	0.0239 (10)	0.0377 (10)	−0.0014 (7)	0.0053 (8)	0.0020 (8)
C7	0.0273 (9)	0.0285 (11)	0.0297 (9)	0.0006 (8)	0.0077 (7)	−0.0052 (8)
C5	0.0321 (10)	0.0342 (12)	0.0229 (9)	−0.0108 (8)	0.0003 (7)	0.0040 (8)
C21	0.0252 (9)	0.0194 (10)	0.0271 (9)	0.0022 (7)	0.0013 (7)	0.0009 (7)
B28	0.0296 (10)	0.0216 (11)	0.0208 (9)	0.0013 (8)	0.0033 (8)	0.0010 (8)
C6	0.0271 (9)	0.0250 (11)	0.0355 (10)	−0.0020 (8)	0.0000 (8)	−0.0011 (8)
C10	0.0255 (9)	0.0275 (11)	0.0316 (10)	−0.0010 (8)	0.0011 (7)	0.0044 (8)
C11	0.0253 (9)	0.0290 (11)	0.0263 (9)	−0.0013 (7)	0.0015 (7)	0.0038 (7)

Geometric parameters (Å, º)

Cl25—C21	1.7510 (19)	C14—C15	1.511 (2)
F31—B28	1.384 (3)	C18—H18A	0.9900
O26—C2	1.221 (2)	C18—H18B	0.9900
N3—C8	1.383 (2)	C18—C17	1.517 (2)
N3—C2	1.395 (2)	C4—H4	0.9500
N3—C4	1.380 (2)	C4—C5	1.342 (3)
N9—N1	1.391 (2)	C17—H17A	0.9900
N9—C8	1.313 (2)	C17—H17B	0.9900
N13—C19	1.405 (2)	C24—H24	0.9500
N13—C14	1.464 (2)	C24—C23	1.382 (3)
N13—C18	1.462 (2)	C15—H15A	0.9900
N16—H16	1.0000	C15—H15B	0.9900
N16—C12	1.502 (2)	C23—H23	0.9500
N16—C17	1.496 (2)	C23—C22	1.389 (3)
N16—C15	1.499 (2)	C22—H22	0.9500
F29—B28	1.389 (3)	C22—C21	1.380 (3)
N1—C2	1.361 (2)	C7—H7	0.9500
N1—C10	1.453 (2)	C7—C6	1.356 (3)
F27—B28	1.377 (3)	C5—H5	0.9500
F30—B28	1.370 (3)	C5—C6	1.430 (3)
C8—C7	1.423 (3)	B28—F1	1.38 (2)
C20—H20	0.9500	B28—F2	1.226 (19)
C20—C19	1.404 (3)	B28—F3	1.38 (2)
C20—C21	1.388 (3)	C6—H6	0.9500
C19—C24	1.406 (3)	C10—H10A	0.9900
C12—H12A	0.9900	C10—H10B	0.9900
C12—H12B	0.9900	C10—C11	1.528 (3)
C12—C11	1.521 (3)	C11—H11A	0.9900
C14—H14A	0.9900	C11—H11B	0.9900
C14—H14B	0.9900
C8—N3—C2	108.44 (15)	C18—C17—H17B	109.3
C4—N3—C8	123.70 (16)	H17A—C17—H17B	107.9
C4—N3—C2	127.84 (16)	C19—C24—H24	119.4
C8—N9—N1	103.43 (14)	C23—C24—C19	121.26 (18)
C19—N13—C14	117.66 (14)	C23—C24—H24	119.4
C19—N13—C18	118.00 (14)	N16—C15—C14	109.78 (14)
C18—N13—C14	111.07 (15)	N16—C15—H15A	109.7
C12—N16—H16	108.1	N16—C15—H15B	109.7
C17—N16—H16	108.1	C14—C15—H15A	109.7
C17—N16—C12	113.72 (14)	C14—C15—H15B	109.7
C17—N16—C15	108.73 (14)	H15A—C15—H15B	108.2
C15—N16—H16	108.1	C24—C23—H23	119.3
C15—N16—C12	109.94 (13)	C24—C23—C22	121.33 (18)
N9—N1—C10	120.88 (15)	C22—C23—H23	119.3
C2—N1—N9	114.19 (15)	C23—C22—H22	121.5
C2—N1—C10	124.87 (16)	C21—C22—C23	117.07 (18)
N3—C8—C7	117.87 (16)	C21—C22—H22	121.5
N9—C8—N3	111.63 (16)	C8—C7—H7	120.8
N9—C8—C7	130.48 (17)	C6—C7—C8	118.43 (18)
C19—C20—H20	120.4	C6—C7—H7	120.8
C21—C20—H20	120.4	C4—C5—H5	119.9
C21—C20—C19	119.22 (17)	C4—C5—C6	120.29 (18)
O26—C2—N3	127.89 (18)	C6—C5—H5	119.9
O26—C2—N1	129.81 (19)	C20—C21—Cl25	118.01 (15)
N1—C2—N3	102.30 (15)	C22—C21—Cl25	118.60 (15)
N13—C19—C24	120.33 (16)	C22—C21—C20	123.37 (18)
C20—C19—N13	121.79 (16)	F31—B28—F29	108.84 (18)
C20—C19—C24	117.73 (17)	F27—B28—F31	110.54 (18)
N16—C12—H12A	108.8	F27—B28—F29	110.5 (2)
N16—C12—H12B	108.8	F30—B28—F31	110.19 (19)
N16—C12—C11	113.62 (14)	F30—B28—F29	108.4 (2)
H12A—C12—H12B	107.7	F30—B28—F27	108.4 (2)
C11—C12—H12A	108.8	F1—B28—F31	105.9 (9)
C11—C12—H12B	108.8	F2—B28—F31	109.9 (8)
N13—C14—H14A	109.5	F2—B28—F1	118.8 (12)
N13—C14—H14B	109.5	F2—B28—F3	112.4 (12)
N13—C14—C15	110.54 (15)	F3—B28—F31	101.6 (11)
H14A—C14—H14B	108.1	F3—B28—F1	106.7 (13)
C15—C14—H14A	109.5	C7—C6—C5	121.53 (19)
C15—C14—H14B	109.5	C7—C6—H6	119.2
N13—C18—H18A	109.4	C5—C6—H6	119.2
N13—C18—H18B	109.4	N1—C10—H10A	108.9
N13—C18—C17	111.26 (15)	N1—C10—H10B	108.9
H18A—C18—H18B	108.0	N1—C10—C11	113.47 (16)
C17—C18—H18A	109.4	H10A—C10—H10B	107.7
C17—C18—H18B	109.4	C11—C10—H10A	108.9
N3—C4—H4	120.9	C11—C10—H10B	108.9
C5—C4—N3	118.17 (18)	C12—C11—C10	110.24 (16)
C5—C4—H4	120.9	C12—C11—H11A	109.6
N16—C17—C18	111.81 (15)	C12—C11—H11B	109.6
N16—C17—H17A	109.3	C10—C11—H11A	109.6
N16—C17—H17B	109.3	C10—C11—H11B	109.6
C18—C17—H17A	109.3	H11A—C11—H11B	108.1
N3—C8—C7—C6	−0.5 (3)	C19—C20—C21—C22	−1.8 (3)
N3—C4—C5—C6	−0.8 (3)	C19—C24—C23—C22	−0.7 (3)
N9—N1—C2—O26	178.61 (19)	C12—N16—C17—C18	−178.65 (15)
N9—N1—C2—N3	−0.7 (2)	C12—N16—C15—C14	−176.59 (15)
N9—N1—C10—C11	−89.6 (2)	C14—N13—C19—C20	−146.04 (17)
N9—C8—C7—C6	178.4 (2)	C14—N13—C19—C24	38.6 (2)
N13—C19—C24—C23	175.19 (18)	C14—N13—C18—C17	−55.4 (2)
N13—C14—C15—N16	−60.5 (2)	C18—N13—C19—C20	−8.4 (3)
N13—C18—C17—N16	54.7 (2)	C18—N13—C19—C24	176.19 (17)
N16—C12—C11—C10	−161.26 (16)	C18—N13—C14—C15	58.7 (2)
N1—N9—C8—N3	0.0 (2)	C4—N3—C8—N9	−179.13 (16)
N1—N9—C8—C7	−178.86 (19)	C4—N3—C8—C7	−0.1 (3)
N1—C10—C11—C12	−57.9 (2)	C4—N3—C2—O26	−0.1 (3)
C8—N3—C2—O26	−178.66 (19)	C4—N3—C2—N1	179.26 (17)
C8—N3—C2—N1	0.67 (19)	C4—C5—C6—C7	0.3 (3)
C8—N3—C4—C5	0.7 (3)	C17—N16—C12—C11	−57.3 (2)
C8—N9—N1—C2	0.4 (2)	C17—N16—C15—C14	58.32 (19)
C8—N9—N1—C10	−177.00 (16)	C24—C23—C22—C21	0.5 (3)
C8—C7—C6—C5	0.4 (3)	C15—N16—C12—C11	−179.50 (16)
C20—C19—C24—C23	−0.4 (3)	C15—N16—C17—C18	−55.81 (19)
C2—N3—C8—N9	−0.5 (2)	C23—C22—C21—Cl25	−177.63 (15)
C2—N3—C8—C7	178.58 (16)	C23—C22—C21—C20	0.8 (3)
C2—N3—C4—C5	−177.66 (18)	C21—C20—C19—N13	−173.91 (17)
C2—N1—C10—C11	93.2 (2)	C21—C20—C19—C24	1.6 (3)
C19—N13—C14—C15	−160.97 (16)	C10—N1—C2—O26	−4.1 (3)
C19—N13—C18—C17	164.44 (16)	C10—N1—C2—N3	176.63 (16)
C19—C20—C21—Cl25	176.58 (14)

(pn180830_uo_eph_1_180814_b12_benzsulf)

Crystal data

C6H5O3S·C10H16NO	F(000) = 344
Mr = 323.40	Dx = 1.315 Mg m^−3
Monoclinic, P21	Cu Kα radiation, λ = 1.54184 Å
a = 5.72587 (4) Å	Cell parameters from 12545 reflections
b = 20.83882 (10) Å	θ = 6.4–78.6°
c = 6.92054 (4) Å	µ = 1.91 mm^−1
β = 98.3547 (5)°	T = 160 K
V = 817.00 (1) Å^3	Needle, colourless
Z = 2	0.70 × 0.22 × 0.17 mm

Data collection

XtaLAB Synergy, Dualflex, Pilatus 200K diffractometer	3292 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source	3290 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.014
ω scans	θmax = 78.8°, θmin = 6.5°
Absorption correction: gaussian CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −6→5
Tmin = 0.488, Tmax = 1.000	k = −26→26
13481 measured reflections	l = −8→8

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.023	w = 1/[σ^2(Fo^2) + (0.0414P)^2 + 0.1072P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.061	(Δ/σ)max = 0.001
S = 1.07	Δρmax = 0.18 e Å^−3
3292 reflections	Δρmin = −0.32 e Å^−3
202 parameters	Absolute structure: Flack x determined using 1579 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
1 restraint	Absolute structure parameter: 0.006 (5)
Primary atom site location: dual

Special details

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.98062 (7)	0.55478 (2)	0.02897 (5)	0.02115 (11)
O13	1.2326 (2)	0.54075 (6)	0.04684 (18)	0.0282 (3)
O1	0.7315 (2)	0.46320 (7)	0.46627 (19)	0.0284 (3)
H1	0.7767	0.4785	0.3657	0.043*
O12	0.8782 (2)	0.57115 (7)	−0.16981 (18)	0.0295 (3)
O11	0.8462 (3)	0.50525 (6)	0.1117 (2)	0.0322 (3)
N1	0.4367 (3)	0.51588 (7)	0.7098 (2)	0.0219 (3)
H1A	0.3899	0.5159	0.8299	0.026*
H1B	0.5950	0.5232	0.7271	0.026*
C5	0.4383 (3)	0.38366 (8)	0.3261 (2)	0.0228 (4)
C16	0.7700 (4)	0.63162 (9)	0.2733 (3)	0.0297 (4)
H16	0.6530	0.5991	0.2675	0.036*
C11	0.9585 (3)	0.62489 (8)	0.1710 (2)	0.0219 (3)
C10	0.6113 (4)	0.33659 (9)	0.3316 (3)	0.0281 (4)
H10	0.7648	0.3445	0.4000	0.034*
C9	0.5615 (4)	0.27811 (10)	0.2379 (3)	0.0333 (4)
H9	0.6807	0.2462	0.2430	0.040*
C12	1.1285 (3)	0.67263 (9)	0.1762 (3)	0.0284 (4)
H12	1.2566	0.6680	0.1042	0.034*
C6	0.2151 (4)	0.37151 (10)	0.2228 (3)	0.0286 (4)
H6	0.0959	0.4035	0.2161	0.034*
C1	0.4880 (3)	0.44825 (8)	0.4260 (2)	0.0222 (3)
H1C	0.4074	0.4824	0.3391	0.027*
C4	0.3172 (4)	0.56994 (9)	0.5946 (3)	0.0302 (4)
H4A	0.3817	0.5743	0.4716	0.045*
H4B	0.3439	0.6098	0.6698	0.045*
H4C	0.1474	0.5613	0.5666	0.045*
C8	0.3384 (4)	0.26632 (10)	0.1370 (3)	0.0344 (4)
H8	0.3040	0.2263	0.0731	0.041*
C2	0.3919 (3)	0.45042 (8)	0.6221 (2)	0.0235 (4)
H2	0.2178	0.4425	0.5981	0.028*
C15	0.7531 (4)	0.68627 (11)	0.3844 (3)	0.0377 (5)
H15	0.6247	0.6910	0.4562	0.045*
C13	1.1093 (4)	0.72702 (10)	0.2872 (3)	0.0348 (4)
H13	1.2253	0.7598	0.2918	0.042*
C7	0.1659 (4)	0.31316 (10)	0.1298 (3)	0.0339 (4)
H7	0.0127	0.3052	0.0608	0.041*
C3	0.5071 (5)	0.40138 (9)	0.7698 (3)	0.0352 (5)
H3A	0.6789	0.4068	0.7870	0.053*
H3B	0.4662	0.3580	0.7220	0.053*
H3C	0.4503	0.4079	0.8952	0.053*
C14	0.9221 (4)	0.73407 (10)	0.3916 (3)	0.0368 (5)
H14	0.9097	0.7715	0.4677	0.044*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0202 (2)	0.02540 (18)	0.01909 (18)	−0.00053 (15)	0.00718 (13)	−0.00015 (15)
O13	0.0232 (7)	0.0386 (8)	0.0239 (6)	0.0071 (5)	0.0071 (5)	−0.0025 (5)
O1	0.0279 (7)	0.0344 (7)	0.0248 (6)	−0.0089 (5)	0.0103 (5)	−0.0041 (5)
O12	0.0267 (7)	0.0402 (8)	0.0211 (6)	−0.0055 (5)	0.0019 (5)	−0.0005 (5)
O11	0.0403 (9)	0.0258 (6)	0.0351 (7)	−0.0036 (6)	0.0204 (6)	−0.0003 (5)
N1	0.0201 (8)	0.0280 (7)	0.0187 (6)	−0.0006 (5)	0.0057 (5)	−0.0015 (5)
C5	0.0266 (10)	0.0271 (8)	0.0158 (7)	−0.0028 (7)	0.0064 (6)	0.0010 (6)
C16	0.0255 (10)	0.0313 (9)	0.0340 (9)	−0.0005 (7)	0.0106 (8)	−0.0032 (8)
C11	0.0198 (9)	0.0252 (8)	0.0200 (7)	0.0018 (6)	0.0012 (6)	0.0024 (6)
C10	0.0264 (10)	0.0298 (9)	0.0275 (8)	−0.0008 (7)	0.0017 (7)	0.0002 (7)
C9	0.0363 (12)	0.0296 (9)	0.0346 (10)	0.0035 (8)	0.0070 (8)	−0.0027 (8)
C12	0.0243 (10)	0.0323 (9)	0.0284 (9)	−0.0025 (7)	0.0030 (7)	0.0023 (7)
C6	0.0247 (10)	0.0350 (9)	0.0267 (8)	0.0005 (7)	0.0058 (7)	−0.0047 (7)
C1	0.0230 (9)	0.0269 (8)	0.0174 (7)	−0.0011 (6)	0.0057 (6)	0.0006 (6)
C4	0.0335 (11)	0.0321 (10)	0.0268 (9)	0.0083 (7)	0.0106 (8)	0.0027 (6)
C8	0.0405 (13)	0.0324 (9)	0.0316 (9)	−0.0075 (8)	0.0097 (8)	−0.0089 (8)
C2	0.0229 (9)	0.0283 (8)	0.0205 (8)	−0.0046 (6)	0.0074 (6)	−0.0015 (6)
C15	0.0331 (12)	0.0424 (11)	0.0402 (11)	0.0029 (9)	0.0142 (9)	−0.0106 (9)
C13	0.0337 (12)	0.0296 (9)	0.0382 (10)	−0.0065 (8)	−0.0049 (8)	−0.0018 (8)
C7	0.0284 (11)	0.0415 (11)	0.0319 (10)	−0.0077 (8)	0.0050 (8)	−0.0096 (8)
C3	0.0574 (14)	0.0300 (10)	0.0202 (9)	−0.0010 (9)	0.0120 (8)	0.0032 (7)
C14	0.0389 (12)	0.0325 (10)	0.0372 (10)	0.0031 (8)	−0.0005 (9)	−0.0108 (8)

Geometric parameters (Å, º)

S1—O13	1.4596 (14)	C12—C13	1.383 (3)
S1—O12	1.4555 (13)	C6—H6	0.9500
S1—O11	1.4536 (14)	C6—C7	1.385 (3)
S1—C11	1.7757 (18)	C1—H1C	1.0000
O1—H1	0.8400	C1—C2	1.538 (2)
O1—C1	1.416 (2)	C4—H4A	0.9800
N1—H1A	0.9100	C4—H4B	0.9800
N1—H1B	0.9100	C4—H4C	0.9800
N1—C4	1.488 (2)	C8—H8	0.9500
N1—C2	1.500 (2)	C8—C7	1.385 (3)
C5—C10	1.391 (3)	C2—H2	1.0000
C5—C6	1.394 (3)	C2—C3	1.526 (3)
C5—C1	1.521 (2)	C15—H15	0.9500
C16—H16	0.9500	C15—C14	1.385 (3)
C16—C11	1.381 (3)	C13—H13	0.9500
C16—C15	1.385 (3)	C13—C14	1.385 (4)
C11—C12	1.389 (3)	C7—H7	0.9500
C10—H10	0.9500	C3—H3A	0.9800
C10—C9	1.390 (3)	C3—H3B	0.9800
C9—H9	0.9500	C3—H3C	0.9800
C9—C8	1.386 (3)	C14—H14	0.9500
C12—H12	0.9500
O13—S1—C11	105.49 (8)	C5—C1—H1C	108.5
O12—S1—O13	112.63 (8)	C5—C1—C2	111.10 (14)
O12—S1—C11	106.20 (8)	C2—C1—H1C	108.5
O11—S1—O13	113.43 (9)	N1—C4—H4A	109.5
O11—S1—O12	112.02 (8)	N1—C4—H4B	109.5
O11—S1—C11	106.37 (8)	N1—C4—H4C	109.5
C1—O1—H1	109.5	H4A—C4—H4B	109.5
H1A—N1—H1B	107.4	H4A—C4—H4C	109.5
C4—N1—H1A	108.4	H4B—C4—H4C	109.5
C4—N1—H1B	108.4	C9—C8—H8	120.2
C4—N1—C2	115.71 (14)	C7—C8—C9	119.58 (18)
C2—N1—H1A	108.4	C7—C8—H8	120.2
C2—N1—H1B	108.4	N1—C2—C1	108.76 (13)
C10—C5—C6	118.84 (17)	N1—C2—H2	108.9
C10—C5—C1	121.76 (17)	N1—C2—C3	107.84 (14)
C6—C5—C1	119.39 (17)	C1—C2—H2	108.9
C11—C16—H16	120.3	C3—C2—C1	113.34 (16)
C11—C16—C15	119.41 (19)	C3—C2—H2	108.9
C15—C16—H16	120.3	C16—C15—H15	119.8
C16—C11—S1	119.42 (14)	C14—C15—C16	120.4 (2)
C16—C11—C12	120.73 (17)	C14—C15—H15	119.8
C12—C11—S1	119.84 (15)	C12—C13—H13	119.8
C5—C10—H10	119.7	C12—C13—C14	120.45 (19)
C9—C10—C5	120.57 (18)	C14—C13—H13	119.8
C9—C10—H10	119.7	C6—C7—H7	119.8
C10—C9—H9	119.9	C8—C7—C6	120.42 (19)
C8—C9—C10	120.11 (19)	C8—C7—H7	119.8
C8—C9—H9	119.9	C2—C3—H3A	109.5
C11—C12—H12	120.3	C2—C3—H3B	109.5
C13—C12—C11	119.32 (19)	C2—C3—H3C	109.5
C13—C12—H12	120.3	H3A—C3—H3B	109.5
C5—C6—H6	119.8	H3A—C3—H3C	109.5
C7—C6—C5	120.47 (19)	H3B—C3—H3C	109.5
C7—C6—H6	119.8	C15—C14—C13	119.67 (19)
O1—C1—C5	113.45 (15)	C15—C14—H14	120.2
O1—C1—H1C	108.5	C13—C14—H14	120.2
O1—C1—C2	106.74 (14)
S1—C11—C12—C13	179.95 (14)	C11—C12—C13—C14	−0.3 (3)
O13—S1—C11—C16	−144.36 (15)	C10—C5—C6—C7	1.0 (3)
O13—S1—C11—C12	36.48 (16)	C10—C5—C1—O1	19.2 (2)
O1—C1—C2—N1	58.18 (17)	C10—C5—C1—C2	−101.0 (2)
O1—C1—C2—C3	−61.74 (19)	C10—C9—C8—C7	0.1 (3)
O12—S1—C11—C16	95.89 (15)	C9—C8—C7—C6	0.0 (3)
O12—S1—C11—C12	−83.27 (15)	C12—C13—C14—C15	0.0 (3)
O11—S1—C11—C16	−23.60 (17)	C6—C5—C10—C9	−0.8 (3)
O11—S1—C11—C12	157.24 (14)	C6—C5—C1—O1	−159.50 (16)
C5—C10—C9—C8	0.3 (3)	C6—C5—C1—C2	80.2 (2)
C5—C6—C7—C8	−0.5 (3)	C1—C5—C10—C9	−179.56 (18)
C5—C1—C2—N1	−177.66 (15)	C1—C5—C6—C7	179.72 (17)
C5—C1—C2—C3	62.4 (2)	C4—N1—C2—C1	62.5 (2)
C16—C11—C12—C13	0.8 (3)	C4—N1—C2—C3	−174.24 (16)
C16—C15—C14—C13	−0.1 (3)	C15—C16—C11—S1	179.86 (16)
C11—C16—C15—C14	0.7 (3)	C15—C16—C11—C12	−1.0 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O11	0.84	1.94	2.7730 (19)	171
N1—H1A···O13^i	0.91	1.93	2.8052 (19)	161
N1—H1B···O12^ii	0.91	1.95	2.792 (2)	153

Symmetry codes: (i) x−1, y, z+1; (ii) x, y, z+1.

(pn180914_uo_eph_1_180814_g4_2)

Crystal data

2(C10H16NO)·C4H4O5·H2O	Z = 1
Mr = 482.56	F(000) = 260
Triclinic, P1	Dx = 1.283 Mg m^−3
a = 5.82130 (7) Å	Cu Kα radiation, λ = 1.54184 Å
b = 7.27088 (8) Å	Cell parameters from 16192 reflections
c = 15.90214 (13) Å	θ = 5.6–78.6°
α = 94.7215 (8)°	µ = 0.79 mm^−1
β = 96.6693 (8)°	T = 160 K
γ = 109.5246 (11)°	Plate, colourless
V = 624.78 (1) Å^3	0.3 × 0.21 × 0.01 mm

Data collection

XtaLAB Synergy, Dualflex, Pilatus 200K diffractometer	4803 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source	4709 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.032
ω scans	θmax = 78.9°, θmin = 2.8°
Absorption correction: gaussian CrysAlisPro 1.171.40.16c (Rigaku Oxford Diffraction, 2018) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −7→7
Tmin = 0.463, Tmax = 1.000	k = −9→9
19924 measured reflections	l = −20→20

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.027	w = 1/[σ^2(Fo^2) + (0.047P)^2 + 0.058P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.074	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.16 e Å^−3
4803 reflections	Δρmin = −0.18 e Å^−3
322 parameters	Absolute structure: Flack x determined using 2188 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
3 restraints	Absolute structure parameter: 0.00 (6)

Special details

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.3528 (3)	0.7437 (2)	0.71174 (9)	0.0280 (3)
H1	0.3828	0.6429	0.6946	0.042*
O11	0.0273 (3)	0.2787 (2)	0.31283 (9)	0.0279 (3)
H11	0.0322	0.1910	0.3435	0.042*
O21	0.4190 (3)	0.4004 (2)	0.66616 (8)	0.0297 (3)
O22	0.3495 (3)	0.13593 (19)	0.57188 (8)	0.0266 (3)
O23	0.5910 (3)	0.65204 (18)	0.55313 (8)	0.0219 (3)
H23	0.4607	0.6786	0.5477	0.033*
O24	1.1434 (3)	0.6384 (2)	0.47409 (9)	0.0298 (3)
O25	0.8005 (3)	0.6055 (2)	0.38907 (8)	0.0253 (3)
O26	0.0579 (4)	0.0217 (3)	0.41762 (12)	0.0467 (5)
H26A	0.163 (7)	0.053 (5)	0.467 (2)	0.050 (8)*
H26B	−0.008 (7)	−0.090 (6)	0.408 (2)	0.052 (9)*
N1	−0.0068 (3)	0.9289 (2)	0.66287 (9)	0.0219 (3)
H1A	0.1386	0.9812	0.6429	0.026*
H1B	−0.1003	0.8193	0.6264	0.026*
N11	0.3851 (3)	0.6649 (2)	0.33349 (10)	0.0232 (3)
H11A	0.2625	0.6384	0.3662	0.028*
H11B	0.5093	0.6315	0.3604	0.028*
C1	0.1194 (4)	0.6869 (3)	0.73851 (11)	0.0211 (4)
H1C	−0.0018	0.5907	0.6919	0.025*
C2	0.0450 (4)	0.8697 (3)	0.74950 (11)	0.0222 (4)
H2	−0.1105	0.8339	0.7751	0.027*
C3	0.2385 (5)	1.0414 (3)	0.80709 (13)	0.0301 (4)
H3A	0.3864	1.0885	0.7798	0.045*
H3B	0.2810	0.9987	0.8618	0.045*
H3C	0.1733	1.1481	0.8169	0.045*
C4	−0.1364 (4)	1.0741 (3)	0.66229 (15)	0.0332 (5)
H4A	−0.1833	1.0927	0.6032	0.050*
H4B	−0.0265	1.2001	0.6941	0.050*
H4C	−0.2847	1.0252	0.6892	0.050*
C5	0.1096 (4)	0.5891 (2)	0.81996 (11)	0.0194 (4)
C6	−0.1179 (4)	0.4745 (3)	0.83863 (12)	0.0252 (4)
H6	−0.2643	0.4600	0.8013	0.030*
C7	−0.1322 (4)	0.3808 (3)	0.91181 (13)	0.0300 (5)
H7	−0.2883	0.3031	0.9244	0.036*
C8	0.0811 (5)	0.4008 (3)	0.96636 (12)	0.0299 (5)
H8	0.0715	0.3371	1.0163	0.036*
C9	0.3070 (4)	0.5135 (3)	0.94768 (12)	0.0298 (5)
H9	0.4532	0.5264	0.9848	0.036*
C10	0.3228 (4)	0.6089 (3)	0.87479 (12)	0.0250 (4)
H10	0.4792	0.6873	0.8627	0.030*
C11	0.2283 (4)	0.3227 (3)	0.26709 (11)	0.0226 (4)
H11C	0.3737	0.3129	0.3041	0.027*
C12	0.2881 (4)	0.5375 (3)	0.24936 (11)	0.0234 (4)
H12	0.4210	0.5691	0.2127	0.028*
C13	0.0666 (4)	0.5759 (3)	0.20437 (13)	0.0291 (4)
H13A	−0.0573	0.5609	0.2425	0.044*
H13B	−0.0045	0.4816	0.1525	0.044*
H13C	0.1190	0.7101	0.1891	0.044*
C14	0.4785 (5)	0.8794 (3)	0.32894 (16)	0.0371 (5)
H14A	0.6054	0.9097	0.2917	0.056*
H14B	0.5497	0.9502	0.3863	0.056*
H14C	0.3422	0.9204	0.3059	0.056*
C15	0.1768 (4)	0.1836 (3)	0.18465 (12)	0.0232 (4)
C16	0.3703 (4)	0.1792 (3)	0.14115 (13)	0.0306 (4)
H16	0.5338	0.2641	0.1629	0.037*
C17	0.3256 (5)	0.0516 (4)	0.06610 (14)	0.0361 (5)
H17	0.4586	0.0510	0.0368	0.043*
C18	0.0899 (5)	−0.0741 (3)	0.03400 (13)	0.0349 (5)
H18	0.0601	−0.1622	−0.0168	0.042*
C19	−0.1021 (5)	−0.0702 (3)	0.07664 (13)	0.0330 (5)
H19	−0.2652	−0.1558	0.0548	0.040*
C20	−0.0590 (4)	0.0581 (3)	0.15145 (13)	0.0275 (4)
H20	−0.1932	0.0594	0.1800	0.033*
C21	0.4244 (4)	0.3198 (3)	0.59479 (11)	0.0200 (4)
C22	0.5342 (4)	0.4477 (2)	0.52644 (11)	0.0194 (4)
H22	0.4122	0.4077	0.4727	0.023*
C23	0.7722 (4)	0.4180 (3)	0.50804 (11)	0.0213 (4)
H23A	0.8790	0.4299	0.5629	0.026*
H23B	0.7312	0.2831	0.4786	0.026*
C24	0.9147 (4)	0.5647 (3)	0.45332 (11)	0.0201 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0328 (9)	0.0230 (6)	0.0352 (7)	0.0131 (7)	0.0184 (6)	0.0089 (5)
O11	0.0340 (10)	0.0255 (7)	0.0297 (6)	0.0129 (7)	0.0135 (6)	0.0110 (5)
O21	0.0395 (10)	0.0278 (7)	0.0247 (6)	0.0131 (7)	0.0100 (6)	0.0060 (5)
O22	0.0314 (9)	0.0185 (6)	0.0293 (6)	0.0059 (6)	0.0081 (6)	0.0064 (5)
O23	0.0188 (7)	0.0163 (6)	0.0316 (6)	0.0074 (5)	0.0042 (5)	0.0024 (5)
O24	0.0200 (9)	0.0329 (7)	0.0364 (7)	0.0081 (7)	0.0030 (6)	0.0100 (6)
O25	0.0251 (8)	0.0292 (7)	0.0245 (6)	0.0114 (6)	0.0050 (5)	0.0087 (5)
O26	0.0580 (13)	0.0214 (8)	0.0461 (9)	0.0009 (8)	−0.0162 (9)	0.0114 (7)
N1	0.0210 (9)	0.0184 (7)	0.0260 (7)	0.0058 (7)	0.0028 (6)	0.0057 (5)
N11	0.0208 (9)	0.0210 (7)	0.0284 (7)	0.0065 (7)	0.0054 (6)	0.0076 (6)
C1	0.0236 (11)	0.0169 (8)	0.0220 (8)	0.0055 (8)	0.0048 (7)	0.0035 (6)
C2	0.0280 (12)	0.0186 (8)	0.0223 (8)	0.0093 (8)	0.0073 (7)	0.0050 (6)
C3	0.0418 (14)	0.0197 (9)	0.0257 (8)	0.0083 (9)	0.0020 (8)	−0.0004 (7)
C4	0.0288 (14)	0.0253 (10)	0.0506 (12)	0.0129 (10)	0.0085 (9)	0.0151 (8)
C5	0.0211 (11)	0.0157 (8)	0.0217 (8)	0.0062 (8)	0.0052 (7)	0.0019 (6)
C6	0.0236 (12)	0.0244 (9)	0.0281 (9)	0.0082 (9)	0.0052 (7)	0.0057 (7)
C7	0.0318 (14)	0.0270 (10)	0.0321 (10)	0.0072 (10)	0.0127 (8)	0.0099 (8)
C8	0.0468 (15)	0.0239 (9)	0.0230 (8)	0.0158 (10)	0.0082 (8)	0.0066 (7)
C9	0.0366 (14)	0.0268 (9)	0.0274 (9)	0.0159 (10)	−0.0024 (8)	0.0012 (7)
C10	0.0229 (11)	0.0211 (8)	0.0294 (9)	0.0063 (8)	0.0026 (7)	0.0022 (7)
C11	0.0233 (11)	0.0242 (9)	0.0230 (8)	0.0108 (8)	0.0034 (7)	0.0072 (6)
C12	0.0262 (12)	0.0230 (9)	0.0235 (8)	0.0099 (9)	0.0064 (7)	0.0076 (7)
C13	0.0354 (13)	0.0278 (10)	0.0269 (8)	0.0148 (10)	0.0006 (8)	0.0085 (7)
C14	0.0386 (15)	0.0201 (9)	0.0481 (12)	0.0050 (10)	0.0023 (10)	0.0086 (8)
C15	0.0249 (11)	0.0233 (9)	0.0247 (8)	0.0119 (9)	0.0032 (7)	0.0070 (7)
C16	0.0250 (12)	0.0344 (10)	0.0338 (10)	0.0128 (10)	0.0040 (8)	0.0019 (8)
C17	0.0409 (15)	0.0432 (13)	0.0343 (10)	0.0256 (12)	0.0117 (9)	0.0055 (9)
C18	0.0511 (16)	0.0286 (10)	0.0289 (10)	0.0209 (11)	0.0015 (9)	0.0024 (8)
C19	0.0363 (14)	0.0233 (9)	0.0344 (10)	0.0072 (10)	−0.0030 (9)	0.0018 (8)
C20	0.0265 (13)	0.0249 (9)	0.0320 (9)	0.0096 (10)	0.0046 (8)	0.0068 (7)
C21	0.0189 (10)	0.0202 (8)	0.0227 (8)	0.0079 (8)	0.0045 (7)	0.0051 (6)
C22	0.0200 (10)	0.0152 (8)	0.0220 (7)	0.0050 (7)	0.0025 (6)	0.0032 (6)
C23	0.0239 (11)	0.0201 (8)	0.0229 (8)	0.0099 (8)	0.0065 (7)	0.0055 (6)
C24	0.0202 (12)	0.0191 (8)	0.0231 (8)	0.0090 (8)	0.0051 (7)	0.0025 (6)

Geometric parameters (Å, º)

O1—C1	1.409 (2)	C6—C7	1.393 (3)
O11—C11	1.410 (2)	C7—C8	1.387 (3)
O21—C21	1.242 (2)	C8—C9	1.378 (3)
O22—C21	1.266 (2)	C9—C10	1.396 (3)
O23—C22	1.426 (2)	C11—C12	1.540 (2)
O24—C24	1.249 (3)	C11—C15	1.523 (2)
O25—C24	1.264 (2)	C12—C13	1.520 (3)
N1—C2	1.504 (2)	C15—C16	1.396 (3)
N1—C4	1.489 (2)	C15—C20	1.382 (3)
N11—C12	1.496 (2)	C16—C17	1.392 (3)
N11—C14	1.481 (3)	C17—C18	1.378 (4)
C1—C2	1.533 (2)	C18—C19	1.380 (4)
C1—C5	1.526 (2)	C19—C20	1.393 (3)
C2—C3	1.516 (3)	C21—C22	1.544 (2)
C5—C6	1.389 (3)	C22—C23	1.528 (3)
C5—C10	1.389 (3)	C23—C24	1.520 (3)
C4—N1—C2	113.94 (15)	N11—C12—C13	110.83 (15)
C14—N11—C12	115.28 (15)	C13—C12—C11	112.99 (17)
O1—C1—C2	107.95 (15)	C16—C15—C11	120.06 (19)
O1—C1—C5	113.82 (15)	C20—C15—C11	121.55 (18)
C5—C1—C2	110.96 (13)	C20—C15—C16	118.39 (18)
N1—C2—C1	108.71 (13)	C17—C16—C15	120.5 (2)
N1—C2—C3	109.97 (15)	C18—C17—C16	120.5 (2)
C3—C2—C1	113.25 (17)	C17—C18—C19	119.19 (19)
C6—C5—C1	119.05 (17)	C18—C19—C20	120.6 (2)
C6—C5—C10	119.42 (17)	C15—C20—C19	120.8 (2)
C10—C5—C1	121.52 (18)	O21—C21—O22	125.48 (17)
C5—C6—C7	120.33 (19)	O21—C21—C22	119.58 (16)
C8—C7—C6	120.1 (2)	O22—C21—C22	114.93 (14)
C9—C8—C7	119.65 (17)	O23—C22—C21	111.93 (13)
C8—C9—C10	120.6 (2)	O23—C22—C23	107.75 (15)
C5—C10—C9	119.9 (2)	C23—C22—C21	110.30 (13)
O11—C11—C12	106.96 (14)	C24—C23—C22	113.30 (14)
O11—C11—C15	112.85 (17)	O24—C24—O25	122.83 (18)
C15—C11—C12	111.30 (14)	O24—C24—C23	117.53 (16)
N11—C12—C11	107.10 (13)	O25—C24—C23	119.64 (18)

(pn180914_uo_eph_1_180814_g5_tart)

Crystal data

2(C10H16NO)·C4H4O6·H2O	F(000) = 536
Mr = 498.56	Dx = 1.271 Mg m^−3
Monoclinic, P21	Cu Kα radiation, λ = 1.54184 Å
a = 6.07189 (12) Å	Cell parameters from 17545 reflections
b = 32.9414 (4) Å	θ = 5.3–78.6°
c = 7.1383 (1) Å	µ = 0.81 mm^−1
β = 114.168 (2)°	T = 160 K
V = 1302.63 (4) Å^3	Plate, colourless
Z = 2	0.48 × 0.35 × 0.01 mm

Data collection

XtaLAB Synergy, Dualflex, Pilatus 200K diffractometer	5216 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source	5091 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.047
ω scans	θmax = 78.8°, θmin = 5.4°
Absorption correction: gaussian CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −6→6
Tmin = 0.370, Tmax = 1.000	k = −41→41
31569 measured reflections	l = −9→9

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.042	w = 1/[σ^2(Fo^2) + (0.0481P)^2 + 0.7643P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.111	(Δ/σ)max < 0.001
S = 1.10	Δρmax = 0.34 e Å^−3
5216 reflections	Δρmin = −0.29 e Å^−3
329 parameters	Absolute structure: Flack x determined using 2347 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
2 restraints	Absolute structure parameter: 0.00 (7)

Special details

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.7143 (4)	0.26054 (8)	0.5007 (3)	0.0275 (5)
H1	0.6533	0.2708	0.5764	0.041*
O11	0.6304 (5)	0.48531 (7)	0.7625 (4)	0.0318 (6)
H11	0.6269	0.4651	0.6897	0.048*
O21	0.5965 (5)	0.29635 (7)	0.7859 (4)	0.0302 (5)
O22	0.7161 (4)	0.34984 (7)	0.6605 (3)	0.0264 (5)
O23	0.5695 (5)	0.33470 (7)	1.0911 (3)	0.0284 (5)
O24	0.1861 (4)	0.36478 (7)	0.7098 (3)	0.0267 (5)
H24	0.0697	0.3696	0.7413	0.040*
O25	0.4980 (4)	0.43635 (7)	1.1083 (3)	0.0265 (5)
O26	0.1307 (4)	0.40866 (7)	0.9929 (3)	0.0258 (5)
O27	0.6413 (6)	0.42735 (8)	0.5191 (4)	0.0424 (7)
H27A	0.5946	0.4304	0.3903	0.064*
H27B	0.6621	0.4023	0.5487	0.064*
N1	1.0461 (5)	0.30687 (8)	0.3902 (4)	0.0226 (5)
H1A	0.8853	0.3115	0.3199	0.027*
H1B	1.0990	0.3229	0.5040	0.027*
N11	0.9458 (5)	0.46709 (8)	1.1555 (4)	0.0211 (5)
H11A	0.7900	0.4587	1.1133	0.025*
H11B	1.0210	0.4496	1.1022	0.025*
C1	0.9679 (6)	0.25797 (9)	0.6105 (4)	0.0213 (6)
H1C	1.0200	0.2815	0.7074	0.026*
C2	1.0815 (6)	0.26317 (9)	0.4576 (4)	0.0230 (6)
H2	1.2587	0.2579	0.5304	0.028*
C3	0.9789 (8)	0.23456 (11)	0.2750 (5)	0.0333 (8)
H3A	0.8087	0.2412	0.1936	0.050*
H3B	0.9921	0.2065	0.3240	0.050*
H3C	1.0696	0.2376	0.1895	0.050*
C4	1.1722 (7)	0.31931 (11)	0.2586 (5)	0.0315 (7)
H4A	1.0964	0.3059	0.1246	0.047*
H4B	1.3425	0.3114	0.3250	0.047*
H4C	1.1608	0.3488	0.2397	0.047*
C5	1.0473 (6)	0.21934 (9)	0.7380 (5)	0.0238 (6)
C6	0.8791 (7)	0.19152 (10)	0.7459 (5)	0.0313 (7)
H6	0.7124	0.1952	0.6616	0.038*
C7	0.9543 (8)	0.15818 (11)	0.8773 (6)	0.0364 (8)
H7	0.8382	0.1395	0.8829	0.044*
C8	1.1954 (8)	0.15214 (11)	0.9988 (5)	0.0358 (8)
H8	1.2453	0.1294	1.0884	0.043*
C9	1.3644 (7)	0.17927 (12)	0.9899 (6)	0.0374 (8)
H9	1.5312	0.1751	1.0722	0.045*
C10	1.2897 (7)	0.21284 (11)	0.8599 (5)	0.0330 (8)
H10	1.4065	0.2315	0.8549	0.040*
C11	0.8614 (6)	0.50329 (10)	0.8363 (4)	0.0234 (6)
H11C	0.9738	0.4841	0.8109	0.028*
C12	0.9472 (7)	0.50860 (9)	1.0698 (5)	0.0263 (7)
H12	1.1160	0.5193	1.1285	0.032*
C13	0.7881 (9)	0.53674 (11)	1.1285 (6)	0.0417 (10)
H13A	0.6235	0.5259	1.0753	0.062*
H13B	0.7861	0.5637	1.0697	0.062*
H13C	0.8519	0.5388	1.2784	0.062*
C14	1.0652 (7)	0.46457 (11)	1.3838 (5)	0.0324 (8)
H14A	1.0671	0.4363	1.4268	0.049*
H14B	0.9757	0.4812	1.4430	0.049*
H14C	1.2312	0.4746	1.4318	0.049*
C15	0.8609 (7)	0.54322 (10)	0.7289 (5)	0.0260 (7)
C16	1.0744 (8)	0.56193 (12)	0.7525 (6)	0.0364 (8)
H16	1.2237	0.5498	0.8386	0.044*
C17	1.0747 (9)	0.59814 (12)	0.6524 (7)	0.0439 (10)
H17	1.2232	0.6106	0.6705	0.053*
H23	0.537 (11)	0.3092 (9)	1.054 (9)	0.066*
C18	0.8589 (9)	0.61598 (11)	0.5268 (6)	0.0439 (10)
H18	0.8580	0.6408	0.4584	0.053*
C19	0.6459 (9)	0.59768 (12)	0.5015 (6)	0.0427 (10)
H19	0.4971	0.6098	0.4147	0.051*
C20	0.6454 (8)	0.56152 (11)	0.6015 (5)	0.0333 (8)
H20	0.4963	0.5492	0.5825	0.040*
C21	0.6422 (5)	0.33331 (10)	0.7830 (4)	0.0204 (6)
C22	0.6050 (6)	0.35999 (9)	0.9434 (4)	0.0220 (6)
H22	0.7526	0.3769	1.0147	0.026*
C23	0.3888 (5)	0.38800 (9)	0.8364 (4)	0.0197 (6)
H23A	0.4299	0.4072	0.7470	0.024*
C24	0.3341 (5)	0.41289 (9)	0.9931 (4)	0.0188 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0196 (12)	0.0377 (12)	0.0258 (11)	0.0030 (9)	0.0099 (9)	−0.0013 (9)
O11	0.0359 (15)	0.0346 (13)	0.0242 (12)	−0.0093 (10)	0.0114 (10)	−0.0035 (9)
O21	0.0334 (14)	0.0268 (12)	0.0369 (12)	0.0003 (9)	0.0208 (11)	−0.0016 (9)
O22	0.0267 (13)	0.0320 (11)	0.0251 (11)	−0.0004 (9)	0.0154 (9)	−0.0004 (8)
O23	0.0318 (14)	0.0350 (13)	0.0215 (11)	0.0025 (10)	0.0139 (9)	0.0076 (9)
O24	0.0139 (11)	0.0417 (13)	0.0233 (10)	−0.0008 (9)	0.0065 (8)	−0.0119 (9)
O25	0.0273 (13)	0.0335 (12)	0.0198 (10)	−0.0077 (9)	0.0105 (9)	−0.0053 (8)
O26	0.0227 (13)	0.0320 (11)	0.0252 (10)	−0.0012 (9)	0.0122 (9)	−0.0047 (9)
O27	0.068 (2)	0.0351 (13)	0.0234 (11)	−0.0025 (13)	0.0184 (12)	−0.0004 (10)
N1	0.0207 (14)	0.0256 (13)	0.0189 (11)	0.0000 (10)	0.0056 (10)	−0.0001 (9)
N11	0.0204 (14)	0.0272 (13)	0.0157 (11)	0.0015 (10)	0.0072 (10)	−0.0013 (9)
C1	0.0199 (16)	0.0256 (14)	0.0183 (13)	0.0011 (11)	0.0077 (11)	−0.0019 (11)
C2	0.0235 (16)	0.0262 (15)	0.0188 (13)	0.0017 (12)	0.0083 (11)	−0.0001 (11)
C3	0.048 (2)	0.0313 (17)	0.0243 (16)	0.0000 (14)	0.0187 (15)	−0.0047 (13)
C4	0.030 (2)	0.0414 (19)	0.0245 (15)	0.0008 (14)	0.0124 (14)	0.0082 (13)
C5	0.0283 (18)	0.0245 (15)	0.0200 (14)	0.0004 (12)	0.0113 (12)	−0.0016 (11)
C6	0.036 (2)	0.0316 (17)	0.0290 (16)	−0.0041 (14)	0.0160 (15)	−0.0009 (13)
C7	0.049 (2)	0.0306 (18)	0.0343 (19)	−0.0120 (15)	0.0218 (17)	−0.0003 (14)
C8	0.054 (2)	0.0277 (17)	0.0269 (17)	0.0009 (15)	0.0174 (16)	0.0042 (13)
C9	0.032 (2)	0.039 (2)	0.0327 (18)	0.0029 (15)	0.0045 (15)	0.0117 (15)
C10	0.033 (2)	0.0317 (17)	0.0319 (17)	−0.0022 (14)	0.0108 (15)	0.0065 (14)
C11	0.0226 (17)	0.0294 (15)	0.0184 (14)	−0.0020 (12)	0.0087 (12)	−0.0027 (11)
C12	0.0323 (19)	0.0250 (15)	0.0200 (14)	−0.0038 (12)	0.0092 (13)	−0.0029 (11)
C13	0.070 (3)	0.0296 (18)	0.0279 (17)	0.0131 (17)	0.0229 (18)	0.0001 (14)
C14	0.033 (2)	0.043 (2)	0.0163 (14)	0.0020 (14)	0.0055 (13)	0.0018 (13)
C15	0.031 (2)	0.0284 (16)	0.0203 (14)	−0.0006 (12)	0.0123 (13)	−0.0020 (11)
C16	0.036 (2)	0.042 (2)	0.0340 (18)	−0.0058 (15)	0.0168 (16)	0.0006 (15)
C17	0.058 (3)	0.042 (2)	0.043 (2)	−0.0143 (19)	0.032 (2)	−0.0046 (17)
C18	0.082 (3)	0.0283 (18)	0.0337 (19)	−0.0006 (18)	0.036 (2)	0.0013 (14)
C19	0.063 (3)	0.0350 (19)	0.0312 (18)	0.0132 (18)	0.0204 (19)	0.0059 (15)
C20	0.042 (2)	0.0340 (18)	0.0258 (16)	0.0035 (15)	0.0154 (15)	−0.0005 (13)
C21	0.0101 (15)	0.0292 (15)	0.0204 (13)	0.0018 (11)	0.0046 (11)	−0.0004 (11)
C22	0.0231 (16)	0.0255 (14)	0.0199 (13)	−0.0020 (11)	0.0112 (12)	0.0015 (11)
C23	0.0156 (15)	0.0261 (14)	0.0169 (12)	−0.0002 (11)	0.0061 (10)	−0.0018 (11)
C24	0.0194 (16)	0.0216 (13)	0.0171 (12)	0.0002 (11)	0.0094 (11)	0.0018 (10)

Geometric parameters (Å, º)

O1—H1	0.8400	C6—C7	1.394 (5)
O1—C1	1.416 (4)	C7—H7	0.9500
O11—H11	0.8400	C7—C8	1.377 (6)
O11—C11	1.411 (4)	C8—H8	0.9500
O21—C21	1.251 (4)	C8—C9	1.382 (6)
O22—C21	1.258 (4)	C9—H9	0.9500
O23—H23	0.88 (3)	C9—C10	1.395 (5)
O23—C22	1.428 (4)	C10—H10	0.9500
O24—H24	0.8400	C11—H11C	1.0000
O24—C23	1.416 (4)	C11—C12	1.539 (4)
O25—C24	1.263 (4)	C11—C15	1.522 (4)
O26—C24	1.242 (4)	C12—H12	1.0000
O27—H27A	0.8498	C12—C13	1.516 (5)
O27—H27B	0.8497	C13—H13A	0.9800
N1—H1A	0.9100	C13—H13B	0.9800
N1—H1B	0.9100	C13—H13C	0.9800
N1—C2	1.505 (4)	C14—H14A	0.9800
N1—C4	1.492 (4)	C14—H14B	0.9800
N11—H11A	0.9100	C14—H14C	0.9800
N11—H11B	0.9100	C15—C16	1.382 (5)
N11—C12	1.499 (4)	C15—C20	1.388 (5)
N11—C14	1.491 (4)	C16—H16	0.9500
C1—H1C	1.0000	C16—C17	1.391 (6)
C1—C2	1.522 (4)	C17—H17	0.9500
C1—C5	1.523 (4)	C17—C18	1.380 (7)
C2—H2	1.0000	C18—H18	0.9500
C2—C3	1.520 (4)	C18—C19	1.370 (7)
C3—H3A	0.9800	C19—H19	0.9500
C3—H3B	0.9800	C19—C20	1.389 (5)
C3—H3C	0.9800	C20—H20	0.9500
C4—H4A	0.9800	C21—C22	1.532 (4)
C4—H4B	0.9800	C22—H22	1.0000
C4—H4C	0.9800	C22—C23	1.529 (4)
C5—C6	1.391 (5)	C23—H23A	1.0000
C5—C10	1.386 (5)	C23—C24	1.529 (4)
C6—H6	0.9500
C1—O1—H1	109.5	O11—C11—C12	107.2 (3)
C11—O11—H11	109.5	O11—C11—C15	112.2 (3)
C22—O23—H23	115 (4)	C12—C11—H11C	108.4
C23—O24—H24	109.5	C15—C11—H11C	108.4
H27A—O27—H27B	109.5	C15—C11—C12	112.2 (2)
H1A—N1—H1B	107.5	N11—C12—C11	106.4 (2)
C2—N1—H1A	108.5	N11—C12—H12	109.2
C2—N1—H1B	108.5	N11—C12—C13	109.5 (3)
C4—N1—H1A	108.5	C11—C12—H12	109.2
C4—N1—H1B	108.5	C13—C12—C11	113.4 (3)
C4—N1—C2	114.9 (3)	C13—C12—H12	109.2
H11A—N11—H11B	107.6	C12—C13—H13A	109.5
C12—N11—H11A	108.6	C12—C13—H13B	109.5
C12—N11—H11B	108.6	C12—C13—H13C	109.5
C14—N11—H11A	108.6	H13A—C13—H13B	109.5
C14—N11—H11B	108.6	H13A—C13—H13C	109.5
C14—N11—C12	114.5 (2)	H13B—C13—H13C	109.5
O1—C1—H1C	107.5	N11—C14—H14A	109.5
O1—C1—C2	107.8 (2)	N11—C14—H14B	109.5
O1—C1—C5	112.8 (3)	N11—C14—H14C	109.5
C2—C1—H1C	107.5	H14A—C14—H14B	109.5
C2—C1—C5	113.4 (3)	H14A—C14—H14C	109.5
C5—C1—H1C	107.5	H14B—C14—H14C	109.5
N1—C2—C1	106.8 (2)	C16—C15—C11	121.1 (3)
N1—C2—H2	108.3	C16—C15—C20	118.1 (3)
N1—C2—C3	111.4 (2)	C20—C15—C11	120.8 (3)
C1—C2—H2	108.3	C15—C16—H16	119.4
C3—C2—C1	113.5 (3)	C15—C16—C17	121.2 (4)
C3—C2—H2	108.3	C17—C16—H16	119.4
C2—C3—H3A	109.5	C16—C17—H17	120.1
C2—C3—H3B	109.5	C18—C17—C16	119.9 (4)
C2—C3—H3C	109.5	C18—C17—H17	120.1
H3A—C3—H3B	109.5	C17—C18—H18	120.3
H3A—C3—H3C	109.5	C19—C18—C17	119.5 (4)
H3B—C3—H3C	109.5	C19—C18—H18	120.3
N1—C4—H4A	109.5	C18—C19—H19	119.7
N1—C4—H4B	109.5	C18—C19—C20	120.7 (4)
N1—C4—H4C	109.5	C20—C19—H19	119.7
H4A—C4—H4B	109.5	C15—C20—C19	120.6 (4)
H4A—C4—H4C	109.5	C15—C20—H20	119.7
H4B—C4—H4C	109.5	C19—C20—H20	119.7
C6—C5—C1	121.1 (3)	O21—C21—O22	125.3 (3)
C10—C5—C1	120.0 (3)	O21—C21—C22	116.4 (3)
C10—C5—C6	118.8 (3)	O22—C21—C22	118.4 (3)
C5—C6—H6	119.9	O23—C22—C21	109.3 (2)
C5—C6—C7	120.2 (3)	O23—C22—H22	108.9
C7—C6—H6	119.9	O23—C22—C23	111.3 (3)
C6—C7—H7	119.7	C21—C22—H22	108.9
C8—C7—C6	120.6 (3)	C23—C22—C21	109.4 (2)
C8—C7—H7	119.7	C23—C22—H22	108.9
C7—C8—H8	120.1	O24—C23—C22	109.7 (2)
C7—C8—C9	119.7 (3)	O24—C23—H23A	108.3
C9—C8—H8	120.1	O24—C23—C24	111.3 (2)
C8—C9—H9	120.1	C22—C23—H23A	108.3
C8—C9—C10	119.9 (4)	C22—C23—C24	111.0 (2)
C10—C9—H9	120.1	C24—C23—H23A	108.3
C5—C10—C9	120.9 (3)	O25—C24—C23	117.1 (3)
C5—C10—H10	119.6	O26—C24—O25	126.0 (3)
C9—C10—H10	119.6	O26—C24—C23	116.9 (3)
O11—C11—H11C	108.4
O1—C1—C2—N1	70.6 (3)	C5—C6—C7—C8	−0.7 (5)
O1—C1—C2—C3	−52.6 (3)	C6—C5—C10—C9	−0.6 (5)
O1—C1—C5—C6	−2.5 (4)	C6—C7—C8—C9	−0.3 (6)
O1—C1—C5—C10	−177.9 (3)	C7—C8—C9—C10	0.8 (6)
O11—C11—C12—N11	58.1 (3)	C8—C9—C10—C5	−0.4 (6)
O11—C11—C12—C13	−62.4 (4)	C10—C5—C6—C7	1.1 (5)
O11—C11—C15—C16	−168.5 (3)	C11—C15—C16—C17	179.1 (3)
O11—C11—C15—C20	10.4 (4)	C11—C15—C20—C19	−179.1 (3)
O21—C21—C22—O23	11.4 (4)	C12—C11—C15—C16	70.7 (4)
O21—C21—C22—C23	−110.6 (3)	C12—C11—C15—C20	−110.4 (3)
O22—C21—C22—O23	−168.3 (3)	C14—N11—C12—C11	169.5 (3)
O22—C21—C22—C23	69.7 (4)	C14—N11—C12—C13	−67.6 (4)
O23—C22—C23—O24	−68.6 (3)	C15—C11—C12—N11	−178.3 (3)
O23—C22—C23—C24	54.9 (3)	C15—C11—C12—C13	61.2 (4)
O24—C23—C24—O25	−176.7 (2)	C15—C16—C17—C18	0.0 (6)
O24—C23—C24—O26	2.1 (4)	C16—C15—C20—C19	−0.2 (5)
C1—C5—C6—C7	−174.4 (3)	C16—C17—C18—C19	−0.2 (6)
C1—C5—C10—C9	175.0 (3)	C17—C18—C19—C20	0.2 (6)
C2—C1—C5—C6	−125.4 (3)	C18—C19—C20—C15	−0.1 (6)
C2—C1—C5—C10	59.2 (4)	C20—C15—C16—C17	0.2 (5)
C4—N1—C2—C1	172.8 (3)	C21—C22—C23—O24	52.3 (3)
C4—N1—C2—C3	−62.7 (4)	C21—C22—C23—C24	175.7 (2)
C5—C1—C2—N1	−163.8 (2)	C22—C23—C24—O25	60.8 (3)
C5—C1—C2—C3	73.0 (3)	C22—C23—C24—O26	−120.4 (3)

(pn180914_uo_eph_2_180814_c6_scr2)

Crystal data

C10H16NO·NO3	F(000) = 488
Mr = 228.25	Dx = 1.256 Mg m^−3
Monoclinic, P21	Cu Kα radiation, λ = 1.54184 Å
a = 6.0401 (3) Å	Cell parameters from 5146 reflections
b = 29.3553 (8) Å	θ = 6.0–76.8°
c = 7.3828 (3) Å	µ = 0.82 mm^−1
β = 112.806 (5)°	T = 160 K
V = 1206.70 (9) Å^3	Plate, colourless
Z = 4	0.40 × 0.07 × 0.01 mm

Data collection

XtaLAB Synergy, Dualflex, Pilatus 200K diffractometer	3727 reflections with I > 2σ(I)
ω scans	Rint = 0.046
Absorption correction: gaussian CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	θmax = 77.1°, θmin = 6.0°
Tmin = 0.811, Tmax = 1.000	h = −4→6
12312 measured reflections	k = −36→36
4637 independent reflections	l = −9→9

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.068	w = 1/[σ^2(Fo^2) + (0.1253P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.190	(Δ/σ)max < 0.001
S = 1.09	Δρmax = 0.63 e Å^−3
4637 reflections	Δρmin = −0.30 e Å^−3
295 parameters	Absolute structure: Flack x determined using 1465 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
1 restraint	Absolute structure parameter: 0.1 (2)

Special details

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.4645 (8)	0.40974 (12)	0.6330 (6)	0.0511 (9)
H1	0.4437	0.4375	0.6035	0.077*
O11	1.0541 (7)	0.58742 (12)	0.8206 (6)	0.0512 (9)
H11	1.0570	0.5591	0.8384	0.077*
O12	0.4335 (7)	0.49914 (13)	0.5078 (6)	0.0562 (9)
O13	0.2075 (8)	0.55884 (13)	0.4450 (7)	0.0603 (11)
O14	0.0677 (8)	0.49420 (15)	0.4881 (7)	0.0653 (11)
O15	0.9936 (8)	0.43770 (13)	1.0100 (7)	0.0601 (10)
O16	1.1647 (7)	0.49810 (13)	0.9579 (6)	0.0568 (9)
O17	0.8092 (8)	0.50216 (15)	0.9638 (7)	0.0652 (11)
N1	0.5062 (9)	0.42691 (14)	1.0175 (6)	0.0449 (10)
H1A	0.6238	0.4358	0.9769	0.054*
H1B	0.3904	0.4488	0.9795	0.054*
N11	0.7159 (8)	0.56996 (14)	0.4439 (6)	0.0443 (9)
H11A	0.8717	0.5612	0.4799	0.053*
H11B	0.6410	0.5482	0.4876	0.053*
N12	0.2327 (8)	0.51762 (14)	0.4790 (6)	0.0453 (10)
N13	0.9878 (8)	0.47920 (16)	0.9788 (6)	0.0477 (10)
C1	0.2821 (9)	0.39444 (16)	0.6945 (7)	0.0436 (10)
H1C	0.1626	0.4195	0.6741	0.052*
C2	0.3988 (10)	0.38326 (15)	0.9147 (7)	0.0422 (10)
H2	0.2714	0.3730	0.9605	0.051*
C3	0.5913 (12)	0.34674 (19)	0.9634 (8)	0.0558 (13)
H3A	0.7235	0.3577	0.9293	0.084*
H3B	0.5226	0.3191	0.8881	0.084*
H3C	0.6519	0.3399	1.1042	0.084*
C4	0.6098 (12)	0.4246 (2)	1.2361 (8)	0.0574 (14)
H4A	0.6655	0.4549	1.2902	0.086*
H4B	0.7453	0.4033	1.2800	0.086*
H4C	0.4866	0.4140	1.2821	0.086*
C5	0.1536 (10)	0.35281 (17)	0.5795 (7)	0.0460 (11)
C6	−0.0518 (11)	0.33614 (19)	0.5996 (9)	0.0543 (13)
H6	−0.1190	0.3523	0.6774	0.065*
C7	−0.1583 (12)	0.2963 (2)	0.5073 (11)	0.0687 (19)
H7	−0.2980	0.2851	0.5221	0.082*
C8	−0.0633 (14)	0.2730 (2)	0.3954 (12)	0.079 (2)
H8	−0.1347	0.2452	0.3351	0.095*
C9	0.1337 (16)	0.2892 (2)	0.3686 (11)	0.078 (2)
H9	0.1964	0.2731	0.2874	0.094*
C10	0.2426 (12)	0.3295 (2)	0.4605 (9)	0.0620 (15)
H10	0.3788	0.3409	0.4409	0.074*
C11	0.8185 (9)	0.60368 (16)	0.7704 (7)	0.0428 (10)
H11C	0.7201	0.5795	0.7995	0.051*
C12	0.7115 (9)	0.61383 (15)	0.5468 (7)	0.0435 (10)
H12	0.5413	0.6241	0.5069	0.052*
C13	0.8514 (12)	0.64980 (19)	0.4892 (8)	0.0560 (14)
H13A	1.0159	0.6391	0.5212	0.084*
H13B	0.8549	0.6780	0.5614	0.084*
H13C	0.7739	0.6556	0.3477	0.084*
C14	0.6027 (11)	0.5710 (2)	0.2270 (8)	0.0548 (13)
H14A	0.5976	0.5401	0.1755	0.082*
H14B	0.6967	0.5907	0.1763	0.082*
H14C	0.4389	0.5829	0.1854	0.082*
C15	0.8124 (9)	0.64633 (17)	0.8827 (7)	0.0428 (10)
C16	1.0234 (10)	0.66778 (19)	1.0012 (8)	0.0497 (12)
H16	1.1736	0.6549	1.0158	0.060*
C17	1.0174 (11)	0.7081 (2)	1.0993 (9)	0.0560 (13)
H17	1.1636	0.7226	1.1784	0.067*
C18	0.8039 (12)	0.7269 (2)	1.0831 (8)	0.0550 (14)
H18	0.8013	0.7544	1.1504	0.066*
C19	0.5898 (11)	0.7055 (2)	0.9671 (8)	0.0537 (13)
H19	0.4404	0.7183	0.9553	0.064*
C20	0.5953 (9)	0.6654 (2)	0.8686 (7)	0.0509 (12)
H20	0.4489	0.6508	0.7906	0.061*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.062 (2)	0.0494 (19)	0.049 (2)	0.0034 (16)	0.0298 (17)	0.0092 (15)
O11	0.045 (2)	0.0510 (19)	0.0492 (19)	0.0044 (14)	0.0092 (15)	0.0040 (15)
O12	0.055 (2)	0.051 (2)	0.068 (2)	0.0043 (18)	0.0293 (19)	0.0066 (18)
O13	0.053 (2)	0.044 (2)	0.086 (3)	0.0021 (16)	0.030 (2)	0.0010 (18)
O14	0.055 (3)	0.062 (2)	0.079 (3)	−0.0058 (19)	0.027 (2)	0.010 (2)
O15	0.061 (3)	0.043 (2)	0.084 (3)	−0.0021 (16)	0.036 (2)	−0.0001 (17)
O16	0.049 (2)	0.050 (2)	0.074 (3)	−0.0041 (17)	0.0259 (18)	0.0049 (18)
O17	0.059 (3)	0.062 (2)	0.077 (3)	0.013 (2)	0.030 (2)	0.011 (2)
N1	0.049 (3)	0.046 (2)	0.044 (2)	−0.0018 (17)	0.0216 (18)	−0.0004 (17)
N11	0.040 (2)	0.045 (2)	0.045 (2)	−0.0024 (17)	0.0137 (17)	0.0004 (17)
N12	0.042 (3)	0.051 (2)	0.041 (2)	−0.0036 (18)	0.0147 (17)	−0.0026 (17)
N13	0.046 (3)	0.056 (3)	0.040 (2)	−0.0014 (19)	0.0149 (18)	−0.0043 (17)
C1	0.045 (3)	0.044 (2)	0.044 (2)	0.0048 (19)	0.021 (2)	0.0024 (19)
C2	0.051 (3)	0.038 (2)	0.042 (2)	−0.0017 (19)	0.022 (2)	0.0018 (18)
C3	0.068 (4)	0.048 (3)	0.044 (3)	0.006 (2)	0.015 (2)	0.003 (2)
C4	0.067 (4)	0.064 (3)	0.039 (3)	−0.001 (3)	0.019 (3)	−0.005 (2)
C5	0.047 (3)	0.046 (2)	0.038 (2)	0.009 (2)	0.008 (2)	0.0027 (19)
C6	0.050 (3)	0.053 (3)	0.055 (3)	0.007 (2)	0.015 (2)	0.010 (2)
C7	0.053 (4)	0.056 (3)	0.077 (4)	0.002 (3)	0.003 (3)	0.017 (3)
C8	0.066 (5)	0.054 (3)	0.075 (5)	0.010 (3)	−0.020 (4)	−0.009 (3)
C9	0.080 (5)	0.074 (4)	0.064 (4)	0.018 (4)	0.010 (4)	−0.022 (3)
C10	0.061 (4)	0.068 (4)	0.053 (3)	0.007 (3)	0.018 (3)	−0.010 (3)
C11	0.038 (3)	0.044 (2)	0.043 (2)	−0.0037 (18)	0.0115 (19)	0.0048 (19)
C12	0.045 (3)	0.037 (2)	0.044 (2)	0.0003 (18)	0.012 (2)	0.0021 (18)
C13	0.069 (4)	0.049 (3)	0.047 (3)	−0.013 (3)	0.019 (2)	0.002 (2)
C14	0.066 (4)	0.053 (3)	0.040 (3)	−0.004 (2)	0.015 (2)	−0.004 (2)
C15	0.042 (3)	0.051 (3)	0.034 (2)	−0.0027 (19)	0.0135 (18)	0.0067 (18)
C16	0.041 (3)	0.057 (3)	0.049 (3)	−0.002 (2)	0.015 (2)	−0.004 (2)
C17	0.049 (3)	0.065 (3)	0.053 (3)	−0.011 (2)	0.019 (2)	−0.010 (2)
C18	0.069 (4)	0.053 (3)	0.042 (3)	0.002 (2)	0.020 (2)	−0.002 (2)
C19	0.053 (3)	0.062 (3)	0.045 (3)	0.008 (2)	0.017 (2)	0.004 (2)
C20	0.037 (3)	0.071 (3)	0.039 (2)	−0.001 (2)	0.0079 (19)	0.000 (2)

Geometric parameters (Å, º)

O1—H1	0.8400	C6—H6	0.9500
O1—C1	1.417 (6)	C6—C7	1.381 (9)
O11—H11	0.8400	C7—H7	0.9500
O11—C11	1.408 (7)	C7—C8	1.358 (12)
O12—N12	1.269 (6)	C8—H8	0.9500
O13—N12	1.233 (6)	C8—C9	1.365 (13)
O14—N12	1.234 (6)	C9—H9	0.9500
O15—N13	1.238 (6)	C9—C10	1.394 (10)
O16—N13	1.265 (6)	C10—H10	0.9500
O17—N13	1.240 (6)	C11—H11C	1.0000
N1—H1A	0.9100	C11—C12	1.551 (7)
N1—H1B	0.9100	C11—C15	1.510 (7)
N1—C2	1.502 (6)	C12—H12	1.0000
N1—C4	1.489 (7)	C12—C13	1.513 (8)
N11—H11A	0.9100	C13—H13A	0.9800
N11—H11B	0.9100	C13—H13B	0.9800
N11—C12	1.500 (7)	C13—H13C	0.9800
N11—C14	1.478 (7)	C14—H14A	0.9800
C1—H1C	1.0000	C14—H14B	0.9800
C1—C2	1.536 (7)	C14—H14C	0.9800
C1—C5	1.518 (7)	C15—C16	1.386 (7)
C2—H2	1.0000	C15—C20	1.392 (8)
C2—C3	1.518 (8)	C16—H16	0.9500
C3—H3A	0.9800	C16—C17	1.394 (8)
C3—H3B	0.9800	C17—H17	0.9500
C3—H3C	0.9800	C17—C18	1.365 (9)
C4—H4A	0.9800	C18—H18	0.9500
C4—H4B	0.9800	C18—C19	1.393 (9)
C4—H4C	0.9800	C19—H19	0.9500
C5—C6	1.393 (8)	C19—C20	1.392 (8)
C5—C10	1.377 (8)	C20—H20	0.9500
C1—O1—H1	109.5	C8—C7—H7	120.0
C11—O11—H11	109.5	C7—C8—H8	119.6
H1A—N1—H1B	107.5	C7—C8—C9	120.7 (6)
C2—N1—H1A	108.5	C9—C8—H8	119.6
C2—N1—H1B	108.5	C8—C9—H9	120.1
C4—N1—H1A	108.5	C8—C9—C10	119.9 (7)
C4—N1—H1B	108.5	C10—C9—H9	120.1
C4—N1—C2	115.2 (4)	C5—C10—C9	120.3 (7)
H11A—N11—H11B	107.4	C5—C10—H10	119.8
C12—N11—H11A	108.3	C9—C10—H10	119.8
C12—N11—H11B	108.3	O11—C11—H11C	109.1
C14—N11—H11A	108.3	O11—C11—C12	107.9 (4)
C14—N11—H11B	108.3	O11—C11—C15	112.0 (4)
C14—N11—C12	116.1 (4)	C12—C11—H11C	109.1
O13—N12—O12	119.2 (4)	C15—C11—H11C	109.1
O13—N12—O14	121.3 (4)	C15—C11—C12	109.7 (4)
O14—N12—O12	119.5 (4)	N11—C12—C11	107.0 (4)
O15—N13—O16	119.4 (4)	N11—C12—H12	109.2
O15—N13—O17	120.8 (4)	N11—C12—C13	109.6 (5)
O17—N13—O16	119.8 (5)	C11—C12—H12	109.2
O1—C1—H1C	108.9	C13—C12—C11	112.7 (4)
O1—C1—C2	108.2 (4)	C13—C12—H12	109.2
O1—C1—C5	111.6 (4)	C12—C13—H13A	109.5
C2—C1—H1C	108.9	C12—C13—H13B	109.5
C5—C1—H1C	108.9	C12—C13—H13C	109.5
C5—C1—C2	110.2 (4)	H13A—C13—H13B	109.5
N1—C2—C1	106.5 (4)	H13A—C13—H13C	109.5
N1—C2—H2	109.0	H13B—C13—H13C	109.5
N1—C2—C3	110.0 (5)	N11—C14—H14A	109.5
C1—C2—H2	109.0	N11—C14—H14B	109.5
C3—C2—C1	113.4 (4)	N11—C14—H14C	109.5
C3—C2—H2	109.0	H14A—C14—H14B	109.5
C2—C3—H3A	109.5	H14A—C14—H14C	109.5
C2—C3—H3B	109.5	H14B—C14—H14C	109.5
C2—C3—H3C	109.5	C16—C15—C11	120.8 (5)
H3A—C3—H3B	109.5	C16—C15—C20	118.3 (5)
H3A—C3—H3C	109.5	C20—C15—C11	121.0 (4)
H3B—C3—H3C	109.5	C15—C16—H16	119.7
N1—C4—H4A	109.5	C15—C16—C17	120.7 (5)
N1—C4—H4B	109.5	C17—C16—H16	119.7
N1—C4—H4C	109.5	C16—C17—H17	119.6
H4A—C4—H4B	109.5	C18—C17—C16	120.8 (5)
H4A—C4—H4C	109.5	C18—C17—H17	119.6
H4B—C4—H4C	109.5	C17—C18—H18	120.3
C6—C5—C1	120.4 (5)	C17—C18—C19	119.5 (5)
C10—C5—C1	121.0 (5)	C19—C18—H18	120.3
C10—C5—C6	118.5 (5)	C18—C19—H19	120.1
C5—C6—H6	119.7	C20—C19—C18	119.9 (5)
C7—C6—C5	120.6 (6)	C20—C19—H19	120.1
C7—C6—H6	119.7	C15—C20—C19	120.9 (5)
C6—C7—H7	120.0	C15—C20—H20	119.5
C8—C7—C6	120.0 (7)	C19—C20—H20	119.5
O1—C1—C2—N1	61.6 (5)	C6—C7—C8—C9	−1.7 (10)
O1—C1—C2—C3	−59.5 (5)	C7—C8—C9—C10	1.5 (11)
O1—C1—C5—C6	−171.6 (4)	C8—C9—C10—C5	0.5 (10)
O1—C1—C5—C10	11.4 (7)	C10—C5—C6—C7	2.2 (8)
O11—C11—C12—N11	59.5 (5)	C11—C15—C16—C17	177.7 (5)
O11—C11—C12—C13	−61.0 (5)	C11—C15—C20—C19	−177.9 (5)
O11—C11—C15—C16	6.8 (6)	C12—C11—C15—C16	−112.9 (5)
O11—C11—C15—C20	−173.8 (4)	C12—C11—C15—C20	66.5 (6)
C1—C5—C6—C7	−174.9 (5)	C14—N11—C12—C11	175.1 (4)
C1—C5—C10—C9	174.7 (6)	C14—N11—C12—C13	−62.4 (6)
C2—C1—C5—C6	68.2 (6)	C15—C11—C12—N11	−178.3 (4)
C2—C1—C5—C10	−108.8 (6)	C15—C11—C12—C13	61.2 (6)
C4—N1—C2—C1	174.6 (5)	C15—C16—C17—C18	1.0 (9)
C4—N1—C2—C3	−62.2 (6)	C16—C15—C20—C19	1.5 (8)
C5—C1—C2—N1	−176.2 (4)	C16—C17—C18—C19	0.0 (9)
C5—C1—C2—C3	62.8 (6)	C17—C18—C19—C20	−0.2 (8)
C5—C6—C7—C8	−0.2 (9)	C18—C19—C20—C15	−0.6 (8)
C6—C5—C10—C9	−2.3 (8)	C20—C15—C16—C17	−1.7 (8)