Structural studies of crystalline forms of triamterene with carboxylic acid, GRAS and API molecules

Pharmaceutical salt solvates (dimethyl sulfoxide, DMSO) of the drug triamterene with the coformers acetic, succinic, adipic, pimelic, azelaic and nicotinic acid and ibuprofen are prepared by liquid-assisted grinding and solvent-evaporative crystallization. The modified ΔpK_a rule as proposed by Cruz-Cabeza [(2012). CrystEngComm, 14, 6362–6365] is in close agreement with the results of this study. All adducts were characterized by X-ray diffraction and thermal analytical techniques, including single-crystal X-ray diffraction, powder X-ray diffraction, differential scanning calorimetry and thermal gravimetric analysis. Hydrogen-bonded motifs combined to form a variety of extended tapes and sheets. Analysis of the crystal structures showed that all adducts existed as salt solvates and contained the amino­pyridinium–carboxyl­ate heterodimer, except for the solvate containing triamterene, ibuprofen and DMSO, as a result of the presence of a strong and stable hemitriamterenium duplex. A search of the Cambridge Structural Database (CSD 5.36, Version 1.18) to determine the frequency of occurrence of the putative supramolecular synthons found in this study showed good agreement with previous work.

1. Introduction

The compound 2,4,7-tri­amino-6-phenyl­pteridine (C₁₂H₁₁N₇), named triamterene (1), is a potassium-sparing diuretic and modest inhibitor of di­hydro­folate reductase. It is marketed under the name of Dyrenium (Well Spring Pharmaceutical Corporation, Concordia Pharmaceutical Inc., Carilion Materials Management and GlaxoSmithKline Inc.) for the treatment of oedema (water retention) and, when combined with hydrochlorthiazide as Maxzide (Mylan Pharmaceuticals) and Dyazide (Cardinal Health and SmithKline Beecham), for the treatment of hypertension (high blood pressure).

This drug has poor solubility in water and a low bioavailability (45 µg ml⁻¹) (Dittert et al., 1964), and is therefore an excellent candidate for a cocrystal or salt screen (Thakuria et al., 2013; Duggirala et al., 2016). A recent study (Ma et al., 2013) found two polymorphs of the salt of 1 with cucurbit­[7]uril (CB[7]). The powder of the CB[7] salt forms a stable complex with 1 in aqueous solution with improved dissolution and solubility by a factor of 1.6 > 1 in 0.1 M hydro­chloric acid. The increased solubility and consequent oral bioavailability of 1 in this case was attributed to the formation of a hydro­philic cylinder composed of two hydro­philic portals containing carbonyl functional groups, in which two molecules of 1 are encapsulated to form a stable complex. As an alternative approach, adduct (cocrystal or salt) formation with carb­oxy­lic acids (Bhatt et al., 2009), Generally Regarded As Safe (GRAS) molecules (Delori et al., 2008; Aitipamula et al., 2014; Lu & Rohani, 2010) and Active Pharmaceutical Ingredients (APIs) (Huang et al., 2014; Sowa et al., 2012; Báthori et al., 2011; Delori, Galek et al., 2013; Grobelny et al., 2011) also provides a means to improve the physicochemical properties of 1. For example, a recent study by Li et al. (2015) reported enhanced solubility and dissolution as a result of salt formation with DL-mandelic acid and saccharin.

Adduct (cocrystal or salt) formation reactions do not only find application in modifying solubility and dissolution profiles (Aitipamula, Vangala et al., 2012; Aitipamula, Wong et al., 2012; Sanphui et al., 2011) but have also been used in altering various other physical properties, such as colour (Stahl & Wermuth, 2008; Pallipurath et al., 2015; Delori et al., 2016), melting point (Friščić & Jones, 2010), stability to humidity (Trask et al., 2005, 2006), tableting properties (Bučar et al., 2015) fluorescence (Bučar et al., 2013; Yan et al., 2013) and polymorphic conversion (Delori et al., 2014).

As shown in Fig. 1, the 2-, 4- and 7-amino groups of the pteridine ring of 1 have good hydrogen-bond donor ability, while the N atoms at positions 1, 3, 5 and 8 can act as potential hydrogen-bond acceptors; however, the N atoms of the amino groups can also act as acceptors, making a total of six donors and seven potential hydrogen-bond acceptors. Since 1 has a large number of potential hydrogen-bond acceptor and donor sites, as well as the option of ionization to form a salt, it is particularly interesting from a crystal engineering standpoint. Furthermore, the cocrystal/salt chemistry of 1 is not well understood, making it a suitable candidate for further experimental work.

Figure 1 Chemical diagram of 1 labelled with the numbering scheme that is used throughout this manuscript.

Within the literature, different strategies have been adopted for the selection of suitable pharmaceutical coformers. One method is based on the hydrogen-bond propensity tool (Bhatt et al., 2009; Delori et al., 2012; Delori, Galek et al., 2013; Huang et al., 2014; Wood et al., 2014) developed by the Cambridge Crystallographic Data Centre (CCDC) to predict the possibility of new polymorphs or adducts based on observed hydrogen bonding in chemically related molecules. Putative pharmaceutical adducts have also been predicted using the CCDC software GOLD (Galek et al., 2007, 2010). A further approach based on molecular shape and polarity descriptors, as a statistical analysis of the Cambridge Structural Database (CSD), found these properties to be the most influential in successful crystal formation (Fábián, 2009). In the present study, we select two classes of coformer for initial screening: mono- and di­carb­oxy­lic acids. Within each of these categories, diversity is created using molecular weight, alkyl or phenyl character and varying the number of available hydrogen-bond donors or acceptors (see Fig. S1 in the supporting information).

The supramolecular synthon approach is widely used in the search for potential cocrystal or salt formation (Desiraju, 1995; Varughese et al., 2010; Arhangelskis et al., 2012). This approach relies on the interaction between complementary functional groups in the formation of hydrogen-bonded adducts (Etter, 1991; Etter & Reutzel, 1991; Etter et al., 1990). In this study, the N1 atom and the 2-amino group in a molecule of 1 are predicted to interact with the carboxyl functional group of the carb­oxy­lic acid. The predicted R₂²(8) synthon will either involve N—H⋯O and O—H⋯N (both neutral) hydrogen bonds to form a cocrystal or N⁺—H⋯O⁻ (charge assisted) and N—H⋯O (neutral) hydrogen bonds to form a salt (see Fig. 2).

Figure 2 Proposed supramolecular heterosynthons between 1 and the acid coformers.

The exact nature of the complex formed is difficult to predict using only synthon information, details of the molecular recognition process (including kinetics) must also be considered. For this reason, the ΔpK_a rule was applied by Cheney, Shan et al. (2010) and Cheney, Weyna et al. (2010). It is widely acknowledged (Childs et al., 2007) that if the calculated ΔpK_a lies in the range 0–3 then prediction becomes unreliable. An improvement of this method has subsequently been proposed by Cruz-Cabeza (2012) and this method is explored in greater detail during this study.

2. Experimental

Pharmaceutical salt solvates (DMSO) of the drug triamterene with the coformers (a) acetic, (b) succinic, (c) adipic, (d) pimelic, (e) azelaic and (f) nicotinic acid, and (g) ibuprofen are prepared by liquid-assisted grinding (LAG) and solvent-evaporative crystallization (SEC). All chemicals were purchased from Sigma–Aldrich and used without further purification. The solvents employed for the crystallizations were spectroscopy grade of the highest purity available.

2.1. Adduct prediction

The method proposed by Cruz-Cabeza (2012) is explored in order to predict the outcome of a given adduct formation reaction where P_obs is the probability (%) of observing AB (cocrystal) and A⁻B⁺ (salt).

The P_obs values for the proposed adduct formation reactions were calculated using the above formulae and compared with the results obtained by experiment in Table S1.

2.2. Liquid-assisted grinding

LAG experiments were performed by placing 200 mg of a physical mixture of 1 with the corresponding acid (a–e) in a 1:1 or 2:1 stoichiometric ratio in a 15 ml stainless-steel grinding jar, accompanied by the addition of 30–50 µl of solvent (DMSO). Grinding was carried out using a Retsch MM200 mixer mill with a frequency of 30 Hz for 30 min together with two stainless steel grinding balls of 7 mm diameter.

2.3. Solvent-evaporative crystallization

Crystals of pure triamterene were obtained by dissolving 10 mg of 1 in 30 ml of methanol and the solution was then heated and filtered prior to SEC. The solutions for the crystallization of 1a–g·DMSO were prepared by dissolving the product of the LAG process (∼50 mg) in DMSO (2 ml) and to aid dissolution, the contents were sonicated prior to gentle heating in a bead bath at 323 K and were filtered (if necessary) into a suitable vial. Colourless high-quality crystals suitable for single-crystal X-ray diffraction analysis (SCXRD) were obtained in all cases by slow evaporation of the methanol or DMSO solution at room temperature for 3–7 d (see Table S2 for a summary of the crystallization data).

2.4. Single-crystal X-ray diffraction

A search of the CSD (5.36, Version 1.18; Groom et al., 2016) revealed two crystal structures of 1 with the refcodes FITZAJ (Schwalbe & Williams, 1987) and FITZAJ01 (Tutughamiarso & Bolte, 2007). These crystal structures have fairly high R₁ values [F_o > 3σ and I > 2σ(I) of 0.09 and 0.0739, respectively] so in our previous work (Hughes et al., 2017), we redetermined the crystal structure of 1 (CCDC deposition code: 1532364) using a crystal grown from methanol. CCDC deposit 1532364 forms the basis for the description of the crystal structure of 1 that follows.

Experimentally, good-quality single crystals of 1a–g·DMSO were chosen by selection under an optical microscope, glued to a glass fibre and mounted on the goniometer of a Bruker diffractometer equipped with an APEX CCD detector at low temperature (150 K for 1d·DMSO, 180 K for 1a·DMSO, 1c·DMSO, 1e·DMSO, 1f·DMSO and 1g·DMSO and 220 K for 1b·DMSO) and graphite-monochromated Mo Kα radiation (λ = 0.71073 Å). In all cases, the data were collected without complication and all crystals were found to be stable throughout the collection period. Intensity data were processed using SAINT (Bruker, 2007), followed by an absorption correction using SADABS (Bruker, 2001). The structures for 1a–g·DMSO were all solved using SIR92 (Altomare et al., 1993) and were refined using the least-squares methods employed in SHELXL2013 (Sheldrick, 2015). All non-H atoms were refined using anisotropic methods, the H atoms either placed in calculated positions by refinement or found by experiment (electron density) where appropriate. The position of the H atom on ring atom N1 was of particular importance and found by experiment in all cases except 1d·DMSO, as the experimental data for this crystal was poor. All structure refinements converged to good R factors and hydrogen bonds were determined using PLATON software (Spek, 2009). All diagrams relating to the crystal structure of 1a–g·DMSO were generated using the Mercury 3.9 module of the CSD Enterprise package (Macrae et al., 2008).

Table 1 contains selected crystallographic parameters for 1 and 1a–g·DMSO. Table S3 (see supporting information) contains further crystallographic details relating to data collection and structure refinement for 1 and 1a–g·DMSO. Table S4 contains details of the labelling scheme for 1 and 1a–g·DMSO, Figs. S2–S9 show the asymmetric units for 1 and 1a–g·DMSO and Tables S5–S12 contain details of the hydrogen bond schemes for 1 and 1a–g·DMSO. The supplementary crystallographic data (CIF files) for 1a–g·DMSO are available in the supporting information for this article or from the Cambridge Crystallographic Data Centre. The supporting information also contains enhanced three-dimensional interactive structural files in Mercury (MRYX) format corresponding to Figs. 3–16 in the manuscript.

Table 1
Selected crystallographic parameters for 1 and 1a–g·DMSO

	1†	1a·DMSO	1b·DMSO	1c·DMSO	1d·DMSO	1e·DMSO	1f·DMSO	1g·DMSO
Formula	C12H11N7	C12H12N7^+·C2H3O2^−·C2H6OS	C12H12N7^+·C4H5O4^−·C2H6OS	2C12H12N7^+·C6H8O4^2−·2C2H6OS	2C12H12N7^+·C7H10O4^2−·2C2H6OS	2C12H12N7^+·C9H14O4^2−·2C2H6OS	C12H12N7^+·C6H4NO2^−·C12H11N7.2C2H6OS	C12H12N7^+·C13H17O2^−·C12H11N7·C2H6OS
Mr	253.28	391.46	449.49	808.95	822.98	851.03	785.92	790.96
Crystal system	Triclinic	Triclinic	Monoclinic	Triclinic	Triclinic	Monoclinic	Monoclinic	Triclinic
Space group			P21/c			P21/n	P21/n
a (Å)	7.4432 (15)	10.8022 (2)	13.5226 (7)	11.0286 (3)	14.0750 (5)	15.0338 (3)	14.8461 (2)	11.2398 (3)
b (Å)	9.993 (2)	13.9084 (2)	14.9966 (7)	13.7429 (4)	14.8889 (6)	11.5004 (2)	12.3081 (3)	13.2439 (3)
c (Å)	16.648 (3)	14.6076 (3)	10.6958 (5)	14.9742 (5)	19.635 (2)	24.3960 (6)	21.2850 (5)	15.4624 (4)
α (°)	77.55 (2)	115.284 (1)	90	115.247 (2)	86.408 (2)	90	90	113.595 (2)
β (°)	87.54 (3)	109.088 (2)	104.179 (2)	109.951 (2)	88.142 (2)	104.539 (1)	105.176 (1)	103.527 (2)
γ (°)	87.09 (3)	90.525 (1)	90	90.122 (2)	71.702 (2)	90	90	91.977 (2)
V (Å^−3)	1207.0 (4)	1846.64 (6)	2102.95 (18)	1900.24 (11)	3898.7 (5)	4082.87 (15)	3753.71 (14)	2029.46 (9)
Z	4	4	4	2	4	4	4	2
Dcalc (Mg m^−1)	1.394	1.408	1.420	1.414	1.402	1.384	1.391	1.294
T (K)	180 (2)	180 (2)	220 (2)	180 (2)	150 (2)	180 (2)	180 (2)	180 (2)
GOF on F^2	1.032	0.935	0.747	1.022	0.945	1.033	0.897	1.021
R1 [I > 2σ(I)]	0.0360	0.0466	0.0364	0.0729	0.0788	0.0587	0.0414	0.0737
wR2	0.0916	0.1179	0.0693	0.1727	0.1951	0.1461	0.0803	0.1891
CCDC	1532364	1579683	1579684	1579685	1579686	1579687	1579688	1579689

†The values for 1 were obtained from the work by Hughes et al. (2017).

2.5. Powder X-ray diffraction

Powder X-ray diffraction (PXRD) data were collected on a Phillips PW3710 diffractometer with nickel-filtered Cu Kα radiation (1.5406 Å) at 40 kV and 40 mA using a scanning RTMS X'Celerator detector. The samples were prepared by gently pressing on a glass slide with a sample groove. Data were collected between 3 ≤ 2θ ≤ 50° at ambient temperature with a step size of 0.0167° at a time per step of 13.97 s for a total scan time of 5 min.

To show that the crystals selected for single-crystal analysis were representative of the bulk powders obtained by LAG, the experimental patterns were compared with the simulated patterns for samples 1a–g·DMSO (see Figs. S10–S16 of the supporting information for reference).

2.6. Differential scanning calorimetry measurements

For differential scanning calorimetry (DSC) analysis, a standard 40 µl aluminium pan was used by placing 3–7 mg of gently ground material such that the bottom of the pan was uniformly covered with sample. The pan was sealed with an aluminium lid using a press and a small hole made in the lid. A Mettler Toledo DSC 822 instrument with an 80 cm³ min⁻¹ nitro­gen purge flow rate was used for the analysis. The temperature range used was 298–673 K with a scan rate of 10 K min⁻¹. Mettler Toledo STARe software (Version 8) was used for the analysis of thermal data obtained.

DSC results for sample 1 are shown for reference in Fig. S17 (see supporting information).

2.7. Thermometric gravimetric analysis measurements

Samples were prepared by placing 7–13 mg of material in a standard 100 µl aluminium pan. A Mettler Toledo TGA/ SDTA851e/SF/1100 instrument with an air purge flow rate of 50 cm³ min⁻¹ was used for the thermogravimetric analysis (TGA). The samples were heated at a rate of 10 K min⁻¹ between 303–673 K and a data analysis was carried out using Mettler Toledo STARe software (Version 8).

DSC and TGA curves for samples 1a–g·DMSO are shown in Figs. S18–S24 (supporting information).

3. Results and discussion

All the crystalline adducts in the present study between 1 and coformers a–g existed as salt solvates (Grothe et al., 2016). The salt/coformer predictions are summarized in Table S1 and the results for all the predicted crystalline adducts were in good agreement with the experiment except for 1a·DMSO and 1g·DMSO where the ΔpK_a values (Hilal et al., 1995) are smallest, thereby providing support for the validity of the modified pK_a rule of Cruz-Cabeza (2012) in this case. Exceptions are known to the pK_a rule, primarily because of the fact that pK_a is a measure of acidity in aqueous solution and the acidity of the same molecules in the crystalline state may be different (Molčanov & Kojić-Prodić, 2010).

A solvent screen revealed 1 to be generally insoluble in most common solvents and it also has a low solubility in most solvents compared with the coformers a–g chosen for this study. LAG experiments using methanol failed since single crystals could not be obtained and the melt cocrystallization experiments were unsuccessful because of the high melting point difference between 1 and the coformers a–g. For these reasons, DMSO was employed as the solvent of choice for the LAG and SEC experiments described in this study since it could be used in relatively small amounts (LAG, 30–50 µl and SEC, 2 ml) and yielded crystalline batches that showed good reproducibility on this scale (see Table S2 for further details).

To enable accurate comparison of the crystal structures, a consistent numbering scheme is used in this study and is shown in Fig. 1. If proton transfer occurs then, from the pK_a values, the transfer is expected to occur from the carb­oxy­lic acid group H1X to the most basic ring nitro­gen, N1, of 1. The numbering scheme for molecules of 1 follow IUPAC recommendations for pteridine-like molecules, whilst individual molecules of 1, coformer and solvent are labelled according to IUCr rules (see Table S4 for details). All asymmetric units and lists of hydrogen bonds are included in Figs. S2–S9 and Tables S5–S12, respectively.

All comparisons of experimental PXRD and simulated PXRD from SCXRD agree closely (see Figs. S10–S12 and S14–S16) except for 1d·DMSO (see Fig. S13) and this is thought to be a result of the preferred orientation of the plate-like crystals noted in this sample.

In an earlier paper (Hughes et al., 2017), we performed a detailed analysis of the crystal structure of 1. We have used this knowledge to create a refined version of the graph-set analysis that can describe the similarities and differences between the crystal structures obtained in this study. Crucial to this refinement of graph-set analysis is the concept of the motif which may be defined as a characteristic pattern of hydrogen bonds within the crystal structure. These interactions may be intermolecular, intramolecular or a combination of the two. Motifs are sets of interactions between functional groups creating a particular pattern, e.g. rings, chains or discrete contacts. Examples of hydrogen-bonding motifs include the common carb­oxy­lic acid ring dimer, the N—H⋯N chain, and the amide ring dimer. As an extension of this concept, we have introduced the term `tape motif' to include groups of two or more individual motifs and supramolecular synthons defined by Desiraju (1995) as `structural units within supermolecules which can be formed and/or assembled by known or conceivable synthetic operations involving intermolecular interactions'. Using these concepts we are able to describe the crystal structure with the view of recognizing the important similarities and differences that exist within the group of structures chosen for this study and beyond.

3.1. The crystal structure of triamterene

The single-crystal data obtained from our earlier paper demonstrates that 1 crystallizes in the triclinic space group with two independent molecules in the asymmetric unit (Z = 4), as shown in Table 1. The asymmetric unit of 1 is shown in Fig. S2 and a list of hydrogen bonds is given in Table S5.

The crystal structure shows molecules of A and B linked into tapes by N—H⋯N hydrogen bonds between the H atoms of the 2-amino groups and the N1 and N3 atoms of adjacent molecules, resulting in the formation of the M1 motif with graph-set notation R₂²(8). Additionally, the M2 motif with graph-set notation R₃³(10 ) exists from the formation of three N—H⋯N hydrogen bonds using the N atoms at positions 1 and 8 interacting with the 2- and 4-amino groups of three molecules of 1 (see Fig. 3a). The M3 motif joins two molecules in adjacent tapes through N—H⋯N hydrogen bonds involving the 7-amino group (see Fig. 3b). It is worth noting that although M1 and M3 motifs are both R₂²(8) homosynthons, they are numbered differently as they occupy different positions on the component molecules of 1.

Figure 3 (a) Motifs M2, M1 and M2 (tape motif TM15) and motif M3 observed in 1. (b) The view along c illustrating the relationship between adjacent tapes using the M3 motif (side view). (c) Packing diagram of the stepped hydrogen-bonded sheets.

Other ring motifs are present (which are not labelled) that satisfy the hydrogen-bond donor and acceptor requirements of 1, but for the purposes of simplification, only the motifs that occur repeatedly in the subsequent adducts of 1 are considered in this discussion. The motifs M2, M1 and M2 combine to form the tape motif TM15 and the hydrogen-bonded tapes seen in the crystal structure of 1 (see Fig. 3a for details).

Overlapping tapes of 1 (Fig. 3b) create a stepped hydrogen-bonded sheet using the M3 motif and these adjacent hydrogen-bonded sheets pack to form the full three-dimensional crystal structure (as seen in Fig. 3c).

3.2. Salt solvate of triamterene with acetic acid and DMSO (1a·DMSO)

Crystals of adduct 1a·DMSO are obtained from a mixture of 1 and a (1:1) in a solution of DMSO to create a crystalline salt solvate in the triclinic space group (see Table 1). The asymmetric unit contains two molecules each of 1, coformer (carb­oxy­lic acid) and DMSO. The asymmetric unit of 1a·DMSO is shown in Fig. S3 and a table of hydrogen bonds is included (see Table S6).

The crystal structure shows molecules of 1 interacting with each other via N—H⋯N hydrogen bonds, creating the M3 and M4 motifs, both with the graph-set notation R₂²(8). 1 is also protonated at the most basic atom (N1) and the complementary groups on 1 and a interact through charge-assisted N⁺—H⋯O⁻ and neutral N—H⋯O hydrogen bonds, creating the M7 motif, also with graph-set notation R₂²(8). DMSO interacts with two molecules of 1 via two N—H⋯O hydrogen bonds, in addition to an intermolecular N—H⋯N bond between adjacent molecules of 1, which creates the M5 motif with R₃²(8) graph-set notation. Motifs M7, M6, M3, M6 and M7 combine to form TM16, and M5, M4 and M5 combine to form TM17 (see Fig. 4a for details).

Figure 4 (a) Motifs M7, M6, M3, M6 and M7 (TM16), and M5, M4 and M5 (TM17) found in the crystal structure of 1a·DMSO. (b) The host–guest network in the form of stepped tapes forming a sheet structure.

These tape motifs create a supramolecular tape of 1 molecules (containing additional acid and solvent molecules) that is interlinked to an adjacent tape of 1 through (C—H⋯O) weak hydrogen bonds that create voids in the crystal structure (Fig. 4a). Around each void, hydrogen-bonded molecules of 1 create A and B cyclic networks. In the A cyclic network, two DMSO molecules occupy the void; however, in the B network, the acid molecules protrude into the void.

The expansion of these combined (A and B) cyclic networks in two dimensions results in the formation of a hydrogen-bonded sheet formed by stepped tapes similar to that seen in 1 and shown in Fig. 4(b) using a space-filling representation.

3.3. Salt solvate of triamterene with succinic acid and DMSO (1b·DMSO)

1b·DMSO crystallizes from DMSO solution as a salt solvate in the monoclinic P2₁/c space group (see Table 1). The asymmetric unit contains one molecule each of 1, b and DMSO (1:1:1). The asymmetric unit of 1b·DMSO is shown in Fig. S4 and the hydrogen bonds are given in Table S7. It can be seen from the asymmetric unit that only one of the two carb­oxy­lic acid groups of b is deprotonated and the H atom is transferred to the most basic atom (N1) of 1; the other carboxyl group is involved in an intramolecular O—H⋯O⁻ hydrogen bond and is therefore not available for deproton­ation.

The crystal structure of 1b·DMSO arises from the formation of two types of hydrogen-bonded network, namely A, which is a ten-membered cyclic hydrogen-bonded network, and B, a six-membered cyclic hydrogen-bonded network similar to that seen in 1a·DMSO. Furthermore, the A network involves two sets of three molecules (trimers) of 1 linked by the M8 motif that interact with two b molecules through the M7 motif present in 1a·DMSO (see Fig. 5). Two DMSO molecules act as a bridge between 1 and b creating the M9 motif and completing the ten-membered cyclic network. The cavity created by the A network is filled by two phenyl rings of 1 and, if these phenyl rings are flipped away from the cavity, voids of 12.7 × 9.0 Å are created. In cyclic network B, two single molecules of 1 connect with two molecules of b, creating two M7 motifs, and the two DMSO molecules protrude into the cavity formed by 1, with b acting as a bridge, joined to 1 by hydrogen bonds and completing the six-membered cyclic network (Fig. 5). We note that in the crystal structure the cyclic networks are made by 1, b and solvent molecules (Fig. 5), as opposed to only 1 and a in 1a·DMSO. Motifs M7, M10, M8 and M9 combine to create the tape motif TM18, M8 and M9 form TM19, and M7, M10 and M8 form TM20, and so complete the hydrogen-bond description of the tape structure found in 1b·DMSO.

Figure 5 The cyclic hydrogen-bonded networks A and B of the crystal structure of 1b·DMSO.

Further expansion of the hydrogen-bonded tape structure in the second dimension results in a sheet structure in which rows of M8 motifs of 1 are interconnected through carb­oxy­lic acid and solvent molecules by weak hydrogen bonds (see Fig. 6 for details).

Figure 6 Motifs M7, M10, M8 and M9 (TM18), M8 and M9 (TM19), and M7, M10 and M8 (TM20) observed in the hydrogen-bonded sheets of 1b·DMSO.

3.4. Salt solvate of triamterene with adipic acid and DMSO (1c·DMSO)

Crystallization of 1 and c from DMSO generated a 2:1 salt (21⁺·c²⁻) together with two molecules of DMSO in the triclinic space group (see Table 1); c acts as a proton donor by the deprotonation of both protons of the carb­oxy­lic acids. The asymmetric unit is shown in Fig. S5 and contains two molecules of 1, one of c and two of DMSO (2:1:2). One DMSO molecule is found to be disordered over two sites with occupancies of 0.7 and 0.3. For the purposes of the crystal structure refinement, geometric constraints and a common isotropic displacement parameter for the non-H atoms were applied to both. A list of hydrogen bonds for 1c·DMSO is given in Table S8.

The crystal structure is a host–guest assembly, with the framework created by molecules of 1 and c, as shown in Figs. 7(a) and 7(b). The interaction between 1 and c is through the M7 motif seen in earlier structures, while the molecules of 1 interlink through M3 and M4 motifs (also present in 1a·DMSO) to form two sets of three molecules (trimers) which link to form sheets. The trimers (tapes) also connect with each other through two acid molecules by hydrogen bonding. This results in the formation of an eight-membered cyclic host network with a cavity of 10.0 × 15.3 Å containing the two molecules of DMSO, as shown in Fig. 7(b).

Figure 7 (a) The eight-membered hydrogen-bonded cyclic host network with a cavity of 15.3 × 10.0 Å dimensions and (b) the cavity filled with two DMSO molecules as guests in 1c·DMSO.

Motifs M5, M4 and M5 (TM16), and M7, M6, M3, M6 and M7 (TM17) create the hydrogen-bonded network structure (see Fig. 8). Such host–guest assemblies are well known in the field of supramolecular chemistry (Bhatt et al., 2009; Galcera et al., 2012).

Figure 8 Motifs M5, M4 and M5 (TM16), and M7, M6, M3, M6 and M7 (TM17) found in the hydrogen-bonded sheets of 1c·DMSO.

3.5. Salt solvate of triamterene with pimelic acid (1d·DMSO)

The molecular adduct of 1d·DMSO crystallizes in the triclinic space group (see Table 1) as a salt between 1 and d in which the acid is found to be doubly deprotonated, transferring protons to two separate molecules of the most basic atom (N1) of 1. The asymmetric unit of the crystal structure is shown in Fig. S6 and contains four molecules of 1 (A, B, C and D), two molecules of d (E and F) and two molecules of DMSO (G). Hydrogen-bond details for 1d·DMSO are given in Table S9.

In the crystal structure, molecules of 1 are connected via N—H⋯N hydrogen bonds joined by M8 motifs to form trimers. The acid molecules act as spacers between the trimers joined by the M7 motif and create a zigzag crinkled supramolecular sheet (Fig. 9a), as seen in 1b·DMSO (see Fig. 6). As noted earlier, this tape is fundamentally different from the supramolecular tape found in 1c·DMSO (see Fig. 7) since, in this case, motifs M3 and M4 are not involved in creating a trimer of 1 molecules.

Figure 9 (a) The eight-membered hydrogen-bonded host network with a cavity of 14.9 × 9.1 Å and the same cavity filled with two DMSO molecules as guests. (b) Motifs M7, M10, M8 and M9 (TM18), M8 and M9 (TM19), and M7, M10 and M8 (TM20) found in the sheet structure formed by the host–guest hydrogen-bonded network. (c) The zigzag nature of the sheet structure seen in 1d·DMSO.

Expansion of the supramolecular tape in the second dimension results in a cyclic eight-membered host network, creating a cavity of 14.9 × 9.1 Å (Fig. 9a). This cavity is filled with two DMSO molecules that act as guests joined to the tapes by M9 motifs with the phenyl rings of 1 also extending into the space (Fig. 9a). Motifs M7, M10, M8 and M9 (TM18), M8 and M9 (TM19), and M7, M10 and M8 (TM20) are also found in the hydrogen-bonded sheet (see Fig. 9b).

A hydrogen-bonded sheet structure formed by the combination of host–guest networks is shown in Fig. 9(c) in which molecular tapes of M8 motifs interconnect with M7 motifs with the acid. Tape motifs TM18, TM19 and TM20 are also found in the hydrogen-bonded sheet seen earlier in 1b·DMSO.

The zigzag stacking of the molecules in this structure is represented by a space-filling model (viewed along the b axis) and is shown in Fig. 9(c).

3.6. Salt solvate of triamterene with azelaic acid (1e·DMSO)

The salt solvate 1e·DMSO is obtained from a DMSO solution by dissolving the LAG product of 1 and e in a 2:1 ratio. The asymmetric unit of the resulting crystal structure is shown in Fig. S7 and contains two molecules each of 1 and DMSO along with one e acid molecule in the monoclinic space group P2₁/n (see Table 1). Both –COOH groups of azelaic acid are deprotonated, as seen in 1c·DMSO and 1d·DMSO. Hydrogen bond details for 1e·DMSO are given in Table S10.

The crystal structure shows molecules of 1e·DMSO form a hydrogen-bonded sheet. Further analysis of the sheet shows that molecules of 1 are joined by M8 motifs to form tapes, as shown in Fig. 10(a). These tapes are held together by molecules of azelaic acid through M7 motifs utilizing charge-assisted N⁺—H⋯O⁻ hydrogen bonds. Motifs M7, M10, M8 and M9 (TM18), M8 and M9 (TM19), and M7, M10 and M8 (TM20) motifs create the hydrogen-bonded network. This association creates an eight-membered cyclic network with voids of 15 × 9.3 Å which are filled by two phenyl rings of 1 molecules along with the two DMSO molecules that act as guests (see Fig. 10b).

Figure 10 (a) The cyclic hydrogen-bonded host network. (b) The same network with each cavity filled with two DMSO molecules showing the motifs M7, M10, M8 and M9 (TM18), M8 and M9 (TM19), and M7, M10 and M8 (TM20). (c) The space-filling model showing the zigzag nature of the 1e·DMSO sheets.

Stacking of these cyclic networks (viewed along the c axis) results in the zigzag hydrogen-bonded sheet structure shown in Fig. 10(c), and these sheets, in turn, stack using van der Waals forces to create the complete three-dimensional crystal structure.

3.7. Salt solvate of triamterene with nicotinic acid (1f·DMSO)

The salt obtained by dissolving a 2:1 LAG (DMSO) sample of 1 and f crystallizes as a DMSO solvate in the monoclinic space group P2₁/n (see Table 1). The resulting asymmetric unit of the crystal structure is shown in Fig. S8 and contains five molecules: two molecules of 1, one molecule of f and two DMSO molecules. In this case, one of the molecules of 1 is protonated (A) while the other remains neutral (B). A list of hydrogen bonds for 1f·DMSO is included in Table S11.

The crystal structure shows that in the supramolecular tape formed between 1, f and DMSO, A and B molecules are connected by M8 motifs in an alternating AB–AB fashion to produce a basic structural ribbon of 1 molecules to which f molecules are attached through the common M7 motif involving N—H⋯O and N⁺—H⋯O⁻ hydrogen bonds. DMSO molecules are connected through M9 motifs, as shown in Fig. 11(a). Motifs M7, M10, M8 and M9 (TM18), M8 and M9 (TM19), and M7, M10 and M8 (TM20) create the hydrogen-bonded tape seen in Fig. 11(a).

Figure 11 (a) The motifs M7, M10, M8 and M9 (TM18), M8 and M9 (TM19), and M7, M10 and M8 (TM20) that create the hydrogen-bonded tape and (b) sheet that forms part of the crystal structure of 1f·DMSO.

Extension of this tape in the second dimension, allows connection between adjacent tapes using weak C—H⋯O hydrogen bonds to produce the hydrogen-bonded sheet shown in Fig. 11(b). Further analysis reveals that the tapes of 1 molecules are stacked in a staggered fashion with the hydro­phobic phenyl groups arranged at a maximum distance from each other (Fig. 12a). Essentially, A molecules interact with the –COO⁻ group of nicotinic acid using the M7 motif and an N—H⋯N hydrogen bond occurs between the N atom of nicotinic acid and the 2-amino group of a B molecule with an H⋯N distance of 2.30 Å, as shown in Fig. 12(b).

Figure 12 (a) Stacking of molecules of 1 to form double hydrogen-bonded chains through (b) nicotinic acid linkages in 1f·DMSO.

In the third dimension, molecules are arranged as parallel zigzag stacked sheets, as seen in the space-filling diagram shown in Fig. 13.

Figure 13 The three-dimensional packing diagram to show the molecules of 1 arranged as zigzag double ribbons in the crystal structure of 1f·DMSO.

3.8. Salt solvate of triamterene with ibuprofen (1g·DMSO)

The salt obtained between 1 and g crystallizes as a DMSO solvate in the triclinic space group , as shown in Table 1. It is obtained by dissolving a mixture of 1 and g in a 2:1 ratio in DMSO. The asymmetric unit is shown in Fig. S9 and contains four molecules in total: two molecules of 1 along with one each of g and DMSO. As in 1f·DMSO, one of the molecules of 1 is protonated (A), while the other remains neutral (B). However, in this case, the DMSO molecule is disordered over two sites with occupancies of 0.9 and 0.1. For the purposes of the crystal structure refinement, geometric constraints and a common isotropic displacement parameter for the non-H atoms were applied to the minor site. A list of hydrogen bonds is included in Table S12.

The crystal structure of 1g·DMSO shows that in the molecular complex the A and B molecules connect through M4 motifs via N—H⋯N hydrogen bonds to yield AA–BB dimers. These further link through M11 and M12 motifs to create an AA–BB–AA zigzag crinkled tape of 1 molecules (Figs. 14 and 21).

Figure 14 The crinkled tape of molecules of 1 observed in the crystal structure of 1g·DMSO.

Figure 21 Supramolecular tape motifs found in 1 and adducts of 1 observed in this study.

The recognition pattern between 1 and g shows that N—H⋯N and N—H⋯O⁻ hydrogen bonds through M13 and M14 motifs hold these molecules together. This is one of the most striking differences observed in the crystal structure of 1g·DMSO in comparison with all adducts described above. In the previous cases, the M7 motif is found between molecules of 1 and all previous coformers containing the –COOH group of a–f. However, in this case, the M7 motif is absent since molecules of 1 combine to form the M11 motif, as shown in Fig. 15. At the other end of the combined motif, two molecules of 1 combine with one O atom of the carboxyl group to form the M14 motif. The DMSO molecules interconnect with 1 through the M5 motif, as observed in 1a·DMSO and 1c·DMSO. The motifs M5, M4 and M5 (TM16), M13, M4 and M13 (TM21), M11, M12 and M14 (TM22), and M11 and M12 (TM23) make up the hydrogen-bonded tape structure seen in 1g·DMSO (see Fig. 15 for details).

Figure 15 The crinkled tape of molecules of 1 with molecules of coformer g and solvent DMSO with the motifs M5, M4 and M5 (TM16), M13, M4 and M13 (TM21), M11, M12 and M14 (TM22), and M11 and M12 (TM23) in the crystal structure of 1g·DMSO.

Further analysis reveals staggered stacking of the tapes of 1 molecules with the hydro­phobic phenyl groups arranged at a maximum distance from each other (Fig. 16a). The stacks of 1 connect with each other through g molecules involving motifs M13 and M14, which results in the formation of pseudo-cyclic networks (as shown in Fig. 16b and highlighted in Fig. 16c).

Figure 16 (a) Stacking of molecules of 1, (b) the linking of molecules of 1 using molecules of g and (c) the specific interactions observed between the stacked hydrogen-bonded layers of 1 and g as seen in the crystal structure of 1g·DMSO.

3.9. Analysis of the hydrogen-bonded motifs in 1 and the reported adducts (1a–g)

Overall, 14 different motifs have been observed in 1 and the reported adducts 1a–g·DMSO (see Figs. 17 and 19). It is recognized that the standard graph-set notation G_d^a(n) introduced by Etter (1991) and described in Bernstein et al. (1995) is not sufficient to accurately describe the interactions found in this study, since various ways of forming the same graph set are possible depending upon the specific functional groups involved.

Figure 17 Hydrogen-bonded motifs between molecules of 1 observed in this study.

As a result, the concepts of motif and supramolecular synthon have been developed and are used throughout this discussion. Additionally, combined (tape) motifs are identified because of the combination of individual motifs in different structural arrangements.

A survey of the CSD (Version 5.36; ConQuest Version 1.18) was conducted in order to better understand the likelihood of these motifs and putative supramolecular synthons occurring in other adducts similar in molecular structure to those found in this study.

3.9.1. Hydrogen-bonded motifs between triamterene (1) molecules

Molecules of 1 are hydrogen bonded by dimeric N—H⋯N hydrogen bonds between the N atoms at positions 1 and 3 in combination with 2-amino groups creating the M1 motif or supramolecular R₂²(8) synthon S1 (see Fig. 18). The M3 motif is created by interaction between the N atoms at position 8 and the 7-amino groups of molecules of 1 on adjacent tapes and may be described as the supramolecular R₂²(8) synthon S1. The other homodimeric motifs only found in the salt solvates between molecules of 1 are M4 and M8 and it is clear from Fig. 17 that they all originate by utilizing different positions of the 1 molecule, but also that they may all be represented by the supramolecular R₂²(8) synthon S1.

Figure 18 Supramolecular synthons observed in this study.

The M2 motif joins three molecules of 1 utilizing the N atoms at positions 1, 3 and 8, and the 2- and 4-amino groups, and creates the supramolecular R₃³(10) synthon S2 (see Fig. 18).

The M11 and M12 motifs are unique in this study and exist between two molecules of 1 in 1g·DMSO, one of which is protonated (A) while the other is neutral (B). M11 and M12 both possess N⁺—H⋯N and N—H⋯N hydrogen bonds and are represented by the supramolecular R₂²(8) synthon S3 (Fig. 18).

Although they have the same graph-set descriptor and indeed the same hydrogen bonds, they represent different supramolecular synthons since they utilize different positions on the molecules of 1 involved in their creation.

The seven motifs found between 1 molecules reported here are shown in Fig. 17.

A CSD analysis undertaken by Delori, Suresh & Pedireddi (2013) revealed that molecules containing the N1—C1—NH₂ functionality had a high propensity to form supramolecular synthon S1. In the present study, a search of the CSD shows that, in the solid state, 52.97% (989 out of 1867) of the crystal structures containing this functionality do form supramolecular synthon S1. Indeed, the largest number of motifs (M1, M3, M4 and M8) between molecules of 1 in this study are represented by this supramolecular synthon (see Fig. 18). Supramolecular synthon S2 is extremely rare and found in only two structures (0.21%) out of the 918 possible crystal structures in the CSD. Finally, the supramolecular synthon S3 is represented by 1.96% (25 structures out of a possible 1277) suitable crystal structures in the CSD.

The various putative supramolecular synthons described in this section are shown in Fig. 18.

3.9.2. Hydrogen-bonded motifs involving triamterene–solvent (1–solvent) and triamterene–coformer (1–coformer) interactions

The M5 and M9 motifs occurring between 1 and the solvent (DMSO), and the M6, M7, M10, M13 and M14 motifs resulting from the interaction between 1 and the coformers (a–g) are shown in Fig. 19.

Figure 19 Hydrogen-bonded motifs of 1–solvent and 1–coformer molecules observed in this study.

M5 involves the interaction of three molecules including the O atom of DMSO using two N—H⋯O hydrogen bonds with the 2- and 4-amino groups of different molecules of 1 and a further N—H⋯N hydrogen bond between the N3 atom and the 4-amino group of adjacent molecules of 1. M5 may be represented by the supramolecular R₃²(8) synthon S4 as seen in Fig. 20 and although M9 is also represented by the supramolecular R₃²(8) synthon S4, it clearly differs from M5 in the position of one of the amino groups on the molecule of 1.

Figure 20 Supramolecular synthons between 1 and solvent, and 1 and coformer molecules observed in this study.

The M6 and M10 motifs seen in Fig. 19 and represented by the supramolecular R₃²(8) synthon S5 in Fig. 20 are formed through charge-assisted N⁺—H⋯O⁻and neutral N—H⋯N hydrogen bonds between 1 and the carboxyl group of the acid. Both of these motifs utilize the protonated N atom of 1 at position 1 and the N atom at position 8, but the N—H⋯N hydrogen bond has a different composition in each motif, involving the 7-amino group for M6 and the 4-amino group for M10.

The unique M13 motif or supramolecular R₃²(8) synthon S6 (see Fig. 20) is only found in 1g·DMSO. This motif results from an N—H⋯N hydrogen bond between atom N3 and the 4-amino group, along with two N—H⋯O hydrogen bonds involving the 2-amino group of one molecule of 1 and the 4-amino group of the other. Similarly, the unique M14 motif or supramolecular R₃²(8) synthon S5 (Fig. 20) in 1g·DMSO results from three hydrogen bonds, but in this case, two charge-assisted N—H⋯O⁻ hydrogen bonds and one N—H⋯N hydrogen bond.

In the M7 motif or supramolecular R₂²(8 ) synthon S7 (Fig. 20) the most basic protonated N atom (N1) and the 2-amino group of 1 interact with the complementary carboxyl group through charge-assisted N⁺—H—O- and N—H⋯O hydrogen bonds. The resulting M7 heterodimer is found to be the most frequent motif seen in this study as it is present in all crystal structures except 1g·DMSO.

The CSD search carried out as part of this study revealed that supramolecular synthons S4 and S5 have a low probability of occurrence (1.68% each) of all the possible synthons in all structures; supramolecular synthon S6 has a frequency of occurrence of 8.41%, while supramolecular synthon S7 has by far the highest frequency of occurrence at 73.45% (617 out of 840 possible crystal structures). These figures are supported by an earlier CSD study by Allen et al. (1999) that showed the probability of forming the R₂²(8 ) supramolecular synthon as ca 95% for mono­carb­oxy­lic acids and 85% for di­carb­oxy­lic acids when no other competing hydrogen-bond donors or acceptors are present. More recently, a study by Delori, Galek et al. (2013) using knowledge-based hydrogen bond propensity calc­ulations (HBPCs) demonstrated the high probability of creating the R₂²(8 ) supramolecular synthon when looking at an antimalarial drug, i.e. pyrimeth­amine, and various carb­oxy­lic acids.

3.9.3. Hydrogen-bonded tape motifs in triamterene and adducts (1a–g)

The TM15 tape motif is specific to 1 and is formed by a combination of three motifs, i.e. M2, M1 and M2. It is thought the interaction between molecules of 1 to create the M1 motif exposes sites rich in hydrogen-bond donors, i.e. the 2-amino groups of two interacting molecules of 1. The hydrogen-bond acceptor sites on adjacent molecules of 1, i.e. the N1, N3 and N8 atoms, interact with these rich hydrogen-bond donors creating the M2 motif and, therefore, the M15 tape motif with the graph-set notation R₄⁴(20 ). The exposed hydrogen-bond donor sites at the 2- and 4-amino groups also result in the formation of the M4 motif and so can interact with the O atom of DMSO by M5 in adducts 1a and 1c·DMSO.

The three motifs (M5, M4 and M5) combine to form the TM16 tape motif with the graph-set notation R₃²(16 ). In the TM17 tape motif, the protonated N1 atoms of two molecules of 1 interact with the 2- and 7-amino and the carboxyl groups, resulting in the formation of a tape motif, which is a combination of five motifs (M7, M6, M3, M6 and M7).

In the TM18 tape motif, the exposed hydrogen-bond donor sites that result from M8 at the 2-amino group and the protonated N1 atom are satisfied by the O atom of DMSO and the carboxyl group of the acid to give M9, M10 and M7 motifs. The TM18 tape motif is therefore composed of four motifs (M7, M10, M8 and M9) and may be represented by the graph-set notation R₄³(20). The TM19 tape motif is represented by the graph set notation R₃²(12 ) and is a combination of M8 and M9. TM20 resembles TM18 since it contains M7, M10 and M8 in the same order but with the difference that M9 (present in M18) is absent and therefore TM20 may be represented by the graph-set descriptor R₃³(16 ).

The TM21 and TM22 tape motifs are unusual since they are present in only one of the adducts (1g·DMSO, see Fig. 15) seen in this study. The TM21 tape motif contains motifs M13, M4 and M13, with donor sites at the 2- and 4-amino groups which are satisfied by an O of the carbonyl group and create the R₄²(16 ) graph set. The TM22 tape motif also contains three motifs (M11, M12 and M14), with donor sites belonging to the 2- and 7-amino groups along with the protonated N1 atom hydrogen bonded to an O atom of the carboxyl group and the N1 atom of the adjacent neutral molecule of 1.

The combined motifs found in 1 and the adducts of 1 are shown in Fig. 21.

4. Summary

The motifs and tape motifs observed in the hydrogen-bonded ribbons of 1 and the various adducts (1a-g·DMSO) are summarized in Fig. 22. By applying colour to represent the motifs, a method of notation (but not mathematical rigour) is developed that better represents the structures. By representing the crystal structure as a repeating sequence of ring structures and by systematically listing the sequence of rings, a pattern is defined. Although this is not the whole story, these patterns can be used to compare the structures.

Figure 22 Summary of hydrogen-bond motifs found in this study. Green represents 1–1 interactions, blue represents 1–solvent interactions, red represents 1–coformer interactions and purple represents solvent–1–coformer interactions.

From Fig. 22 it can be seen that the crystal structures in this study can be divided into four groups.

(i) 1 can be seen to be composed of only 1–1 interactions. The M1 and M2 motifs combine to form the TM15 tape motif and the hydrogen-bonded ribbon. M3 forms an essential connection between adjacent ribbons in 1 that allows the hydrogen-bonded sheet to be formed by extension of the structure in the direction orthogonal to that of the ribbon. Interestingly, M3 is also found in 1a·DMSO and 1c·DMSO, but this time within the ribbon structure and it may therefore be regarded as a synthon.

(ii) 1a·DMSO and 1c·DMSO contain the motifs M3, M4, M5, M6 and M7 that combine to form TM16 and TM17. These crystal structures contain very similar sheet structures and, looking at the unit-cell dimensions, 1a·DMSO and 1c·DMSO may be regarded as being isostructural.

(iii) 1b·DMSO, 1d·DMSO, 1e·DMSO and 1f·DMSO contain motifs M7, M8, M9 and M10 that combine to form TM18, TM19 and TM20. Interestingly, 1b·DMSO, 1d·DMSO and 1e·DMSO have similar hydrogen-bonded sheets which differ considerably from 1f·DMSO that contains a hydrogen-bonded double ribbon.

(iv) 1g·DMSO has a unique connectivity and crystal structure resulting from (in part) the presence of the unique 1–1 motifs M11 and M12 that combine to form a unique dimer structure (TM23).

Furthermore, it can be seen from Fig. 22 that the hydrogen-bonded motif M7 is present in all cases except for 1g·DMSO. This is one of the motifs predicted by the supramolecular synthon approach and ΔpK_a discussed earlier (see Fig. 2 for details). The CSD search outlined in §3.9.2 shows the probability of occurrence of M7 in molecules containing the functional groups required to create this motif, such as pyrimethamine (Delori, Galek et al., 2013) and the triazines (Bhatt et al., 2009) and carb­oxy­lic acids, is quite high at 73.45%.

To confirm the position of the proton in 1g·DMSO, a further CSD study was undertaken to look for similar three-centred dimers in the presence of carb­oxy­lic acids. Among the results of this search, the hemicytosinium duplexes described by Perumalla et al. (2013) were found. In this paper, experiments were performed to determine the ability of cytosine to form salts with a series of acids. It was stated that the cytosinium ion was present only with acids of a pK_a > 4.2 and less strong acids were unable to disrupt the relatively stable duplex structure. It is proposed that a similar kinetic mechanism is found in this study where triamterene forms a stable three-centred duplex (hemitriamterenium) containing the M11 and M12 motifs that cannot be disrupted by ibuprofen with a pK_a value of 5.2 but can form the triamterenium ion with the stronger carb­oxy­lic acids in the pK_a range 4.2–4.76.

5. Conclusions

The salt solvate adducts 1a–g·DMSO were prepared using conventional screening techniques, i.e. LAG and SEC. Adduct formation was confirmed by SCXRD, PXRD, DSC and TGA. The results are in accordance with the modified ΔpK_a rule proposed by Cruz-Cabeza (2012). To overcome some of the limitations of graph-set theory, the concepts of motif, tape motif and supramolecular synthon are introduced to describe the crystal structures since it has been established that molecules of 1 can adopt different orientations corresponding to the same graph-set descriptor. It is noteworthy that the M1 motif is seen only in the crystal structure of 1 but is not observed in any of the other crystal structures because of its replacement by M7 in 1a–f·DMSO and M11 in 1g·DMSO. The present study and the CSD survey carried out by Delori, Suresh & Pedireddi (2013) both suggest M7 to be a very robust motif. In fact, the M7 motif is present in all the reported adducts found in this study except for 1g·DMSO. It should also be noted that this is the same motif proposed in Fig. 2, resulting from the crystal engineering approach which emphasizes the identification of systematic patterns of hydrogen bonds from known crystal structures. Overall seven adducts (1a–g. DMSO) containing 14 motifs, 8 supramolecular tape motifs and 7 supramolecular synthons are reported and their structural relationships explored. The anomalous behaviour of 1 g·DMSO is explained by the inability of ibuprofen to disrupt the stable hemitriamterenium duplex.

Supporting information

Computing details

For all structures, data collection: Collect (Nonius B.V. 1998); cell refinement: HKL SCALEPACK (Otwinowski & Minor 1997); data reduction: HKL DENZO and SCALEPACK (Otwinowski & Minor 1997); program(s) used to solve structure: SIR92 (Altomare et al. 1994). Program(s) used to refine structure: SHELXL2013 (Sheldrick, 2013) for 1a_DMSO, 1b_DMSO, 1c_DMSO, 1e_DMSO, 1f_DMSO; SHELXL97 (Sheldrick 1997) for 1d_DMSO, 1g_DMSO. For all structures, molecular graphics: Mercury (Macrae et al., 2008). Software used to prepare material for publication: SHELXL for 1a_DMSO, 1b_DMSO, 1c_DMSO, 1e_DMSO, 1f_DMSO; SHELXL97 (Sheldrick 1997) for 1d_DMSO, 1g_DMSO.

Triamterenium acetate, DMSO solvate (1a_DMSO)

Crystal data

C12H12N7^+·C2H6OS·C2H3O2^−	Z = 4
Mr = 391.46	F(000) = 824
Triclinic, P1	Dx = 1.408 Mg m^−3
a = 10.8022 (2) Å	Mo Kα radiation, λ = 0.7107 Å
b = 13.9084 (2) Å	Cell parameters from 10617 reflections
c = 14.6076 (3) Å	θ = 1.0–30.0°
α = 115.284 (1)°	µ = 0.21 mm^−1
β = 109.088 (2)°	T = 180 K
γ = 90.525 (1)°	Block, colourless
V = 1846.64 (6) Å^3	0.25 × 0.12 × 0.10 mm

Data collection

Nonius Kappa CCD diffractometer	10617 independent reflections
Radiation source: fine-focus sealed tube	6401 reflections with I > 2σ(I)
None monochromator	Rint = 0.042
Thin slice ω and φ scans	θmax = 30.0°, θmin = 3.6°
Absorption correction: multi-scan multi-scan from symmetry-related measurements Sortav (Blessing 1995)	h = −15→14
Tmin = 0.901, Tmax = 0.999	k = −19→18
24626 measured reflections	l = −14→20

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.047	Hydrogen site location: difference Fourier map
wR(F^2) = 0.126	All H-atom parameters refined
S = 0.94	w = 1/[σ^2(Fo^2) + (0.0695P)^2] where P = (Fo^2 + 2Fc^2)/3
10617 reflections	(Δ/σ)max < 0.001
655 parameters	Δρmax = 0.67 e Å^−3
0 restraints	Δρmin = −0.44 e Å^−3

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
N1A	0.17280 (11)	0.57437 (11)	0.35562 (10)	0.0229 (3)
C2A	0.05142 (13)	0.59853 (13)	0.31573 (12)	0.0239 (3)
N2A	0.04629 (14)	0.67427 (12)	0.28419 (12)	0.0331 (3)
N3A	−0.06158 (11)	0.54961 (11)	0.30881 (10)	0.0246 (3)
C4A	−0.05437 (13)	0.47345 (12)	0.34241 (12)	0.0228 (3)
N4A	−0.16567 (12)	0.42709 (12)	0.33735 (12)	0.0286 (3)
C4AA	0.07019 (13)	0.44160 (12)	0.38249 (12)	0.0217 (3)
N5A	0.07477 (11)	0.35713 (10)	0.40616 (10)	0.0228 (3)
C6A	0.19142 (13)	0.32920 (12)	0.43795 (12)	0.0219 (3)
C7A	0.31158 (13)	0.39361 (12)	0.45524 (12)	0.0228 (3)
N7A	0.43140 (12)	0.37284 (12)	0.49680 (12)	0.0295 (3)
N8A	0.30584 (11)	0.47503 (10)	0.42881 (10)	0.0230 (3)
C8AA	0.18412 (13)	0.49606 (12)	0.38962 (12)	0.0210 (3)
C9A	0.19363 (13)	0.22864 (12)	0.45035 (12)	0.0235 (3)
C10A	0.13629 (16)	0.21453 (15)	0.51756 (14)	0.0310 (4)
C11A	0.12724 (17)	0.11655 (16)	0.52084 (16)	0.0373 (4)
C12A	0.17298 (16)	0.03115 (15)	0.45542 (15)	0.0354 (4)
C13A	0.23056 (16)	0.04472 (15)	0.38950 (14)	0.0315 (4)
C14A	0.24234 (15)	0.14300 (14)	0.38726 (13)	0.0271 (3)
N1B	0.33114 (12)	0.43741 (10)	0.16905 (10)	0.0229 (3)
C2B	0.45354 (13)	0.42190 (12)	0.22065 (12)	0.0226 (3)
N2B	0.45957 (14)	0.34979 (12)	0.25696 (12)	0.0282 (3)
N3B	0.56766 (11)	0.47624 (11)	0.23461 (10)	0.0255 (3)
C4B	0.56048 (14)	0.54651 (13)	0.19385 (13)	0.0255 (3)
C4AB	0.43474 (13)	0.56628 (13)	0.13775 (12)	0.0234 (3)
N4B	0.67234 (14)	0.59768 (13)	0.20525 (14)	0.0373 (4)
N5B	0.42955 (11)	0.64195 (10)	0.10210 (10)	0.0236 (3)
C6B	0.31226 (13)	0.66138 (12)	0.05765 (12)	0.0221 (3)
C7B	0.19169 (13)	0.59773 (12)	0.04065 (12)	0.0224 (3)
N7B	0.07306 (13)	0.61269 (13)	−0.01150 (13)	0.0328 (3)
N8B	0.19716 (11)	0.52335 (10)	0.07690 (10)	0.0237 (3)
C8AB	0.31933 (13)	0.51014 (12)	0.12724 (12)	0.0217 (3)
C9B	0.30992 (13)	0.75360 (13)	0.03081 (12)	0.0229 (3)
C10B	0.34291 (17)	0.74670 (17)	−0.05564 (15)	0.0343 (4)
C11B	0.35784 (19)	0.83637 (19)	−0.07114 (19)	0.0465 (5)
C12B	0.34014 (17)	0.93355 (17)	−0.00130 (17)	0.0438 (5)
C13B	0.30430 (17)	0.94238 (16)	0.08426 (16)	0.0397 (4)
C14B	0.28863 (16)	0.85209 (14)	0.09990 (14)	0.0313 (4)
C1C	0.3050 (2)	0.1919 (2)	0.9589 (2)	0.0527 (6)
O1C	0.17699 (11)	0.23199 (11)	0.79740 (10)	0.0432 (3)
S1C	0.16603 (4)	0.24236 (4)	0.90154 (4)	0.03472 (12)
C2C	0.0360 (3)	0.1365 (2)	0.8598 (2)	0.0588 (6)
C1D	0.5869 (3)	0.1097 (2)	0.3693 (3)	0.0630 (7)
O1D	0.70351 (11)	0.27236 (11)	0.36551 (11)	0.0434 (3)
S1D	0.73929 (4)	0.19095 (4)	0.40657 (4)	0.03484 (12)
C2D	0.8063 (3)	0.0960 (2)	0.3155 (2)	0.0613 (7)
C1E	0.62951 (14)	0.23148 (13)	0.66048 (12)	0.0246 (3)
O1E	0.61539 (10)	0.29807 (10)	0.62197 (10)	0.0361 (3)
C2E	0.50478 (17)	0.16465 (17)	0.64250 (17)	0.0346 (4)
O2E	0.73846 (10)	0.21589 (9)	0.71096 (9)	0.0337 (3)
C1F	0.13081 (14)	0.23043 (13)	0.15957 (12)	0.0258 (3)
O1F	0.11401 (10)	0.30967 (10)	0.13920 (10)	0.0346 (3)
C2F	0.00873 (18)	0.16139 (18)	0.14287 (17)	0.0386 (4)
O2F	0.24120 (10)	0.20366 (10)	0.19082 (10)	0.0384 (3)
H1XA	0.2443 (17)	0.6137 (15)	0.3609 (14)	0.032 (5)*
H2A	0.1179 (19)	0.7055 (15)	0.2861 (14)	0.037 (5)*
H3A	−0.028 (2)	0.6919 (16)	0.2629 (15)	0.044 (5)*
H4A	−0.2396 (18)	0.4479 (14)	0.3118 (13)	0.031 (5)*
H5A	−0.1666 (16)	0.3788 (15)	0.3581 (14)	0.035 (5)*
H6A	0.4382 (15)	0.3327 (14)	0.5265 (13)	0.023 (4)*
H7A	0.5026 (19)	0.4205 (17)	0.5128 (15)	0.046 (5)*
H10A	0.1006 (16)	0.2704 (14)	0.5572 (13)	0.031 (5)*
H11A	0.0823 (18)	0.1080 (16)	0.5604 (15)	0.043 (5)*
H12A	0.1665 (17)	−0.0335 (16)	0.4571 (14)	0.040 (5)*
H13A	0.2603 (16)	−0.0073 (15)	0.3526 (14)	0.029 (5)*
H14A	0.2795 (17)	0.1504 (15)	0.3402 (14)	0.038 (5)*
H1XB	0.2609 (18)	0.3973 (16)	0.1623 (14)	0.038 (5)*
H2B	0.3823 (18)	0.3088 (15)	0.2391 (13)	0.030 (4)*
H3B	0.5300 (17)	0.3387 (14)	0.2880 (13)	0.027 (5)*
H4B	0.7444 (19)	0.5872 (15)	0.2356 (14)	0.032 (5)*
H5B	0.6700 (18)	0.6485 (17)	0.1863 (16)	0.048 (6)*
H6B	0.0681 (16)	0.6547 (15)	−0.0380 (13)	0.027 (5)*
H7B	0.002 (2)	0.5691 (17)	−0.0295 (16)	0.047 (6)*
H10B	0.3529 (18)	0.6834 (16)	−0.0995 (15)	0.044 (6)*
H11B	0.374 (2)	0.8251 (18)	−0.1330 (18)	0.063 (7)*
H12B	0.3511 (18)	0.9934 (17)	−0.0114 (15)	0.045 (5)*
H13B	0.2904 (19)	1.0071 (18)	0.1300 (16)	0.052 (6)*
H14B	0.2654 (18)	0.8558 (16)	0.1546 (15)	0.043 (5)*
H1C	0.380 (2)	0.242 (2)	0.9726 (19)	0.077 (8)*
H2C	0.3113 (17)	0.1280 (17)	0.9066 (16)	0.039 (5)*
H3C	0.301 (2)	0.191 (2)	1.026 (2)	0.077 (7)*
H4C	−0.047 (4)	0.144 (3)	0.821 (3)	0.134 (14)*
H5C	0.029 (3)	0.136 (2)	0.919 (2)	0.094 (9)*
H6C	0.061 (3)	0.072 (3)	0.818 (3)	0.113 (12)*
H1D	0.530 (4)	0.157 (4)	0.404 (3)	0.174 (18)*
H2D	0.605 (3)	0.051 (3)	0.381 (3)	0.119 (12)*
H3D	0.547 (3)	0.091 (2)	0.294 (2)	0.096 (10)*
H4D	0.894 (3)	0.134 (2)	0.321 (2)	0.115 (11)*
H5D	0.742 (3)	0.067 (2)	0.242 (2)	0.086 (8)*
H6D	0.820 (2)	0.039 (2)	0.3360 (19)	0.072 (7)*
H1E	0.517 (2)	0.1496 (19)	0.7051 (19)	0.073 (7)*
H2E	0.481 (2)	0.092 (2)	0.5764 (18)	0.063 (7)*
H3E	0.431 (2)	0.1961 (19)	0.6255 (18)	0.068 (7)*
H1F	−0.029 (3)	0.096 (3)	0.068 (3)	0.121 (11)*
H2F	−0.061 (3)	0.192 (2)	0.135 (2)	0.105 (10)*
H3F	0.028 (2)	0.131 (2)	0.189 (2)	0.085 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0159 (6)	0.0249 (7)	0.0332 (7)	0.0045 (5)	0.0073 (5)	0.0190 (6)
C2A	0.0196 (7)	0.0262 (9)	0.0287 (8)	0.0051 (6)	0.0073 (6)	0.0161 (7)
N2A	0.0192 (7)	0.0395 (9)	0.0535 (9)	0.0084 (6)	0.0102 (6)	0.0348 (8)
N3A	0.0171 (6)	0.0291 (8)	0.0339 (7)	0.0062 (5)	0.0079 (5)	0.0209 (6)
C4A	0.0177 (7)	0.0239 (8)	0.0270 (8)	0.0046 (6)	0.0059 (6)	0.0135 (7)
N4A	0.0167 (6)	0.0333 (8)	0.0459 (9)	0.0062 (5)	0.0082 (6)	0.0292 (7)
C4AA	0.0188 (7)	0.0214 (8)	0.0274 (8)	0.0043 (5)	0.0071 (6)	0.0143 (7)
N5A	0.0187 (6)	0.0242 (7)	0.0272 (7)	0.0044 (5)	0.0067 (5)	0.0144 (6)
C6A	0.0192 (7)	0.0226 (8)	0.0257 (7)	0.0043 (6)	0.0068 (6)	0.0136 (7)
C7A	0.0181 (7)	0.0235 (8)	0.0273 (8)	0.0046 (6)	0.0063 (6)	0.0134 (7)
N7A	0.0180 (7)	0.0310 (8)	0.0477 (9)	0.0051 (6)	0.0069 (6)	0.0289 (7)
N8A	0.0168 (6)	0.0239 (7)	0.0310 (7)	0.0043 (5)	0.0071 (5)	0.0161 (6)
C8AA	0.0182 (7)	0.0211 (8)	0.0246 (7)	0.0055 (5)	0.0065 (5)	0.0121 (6)
C9A	0.0168 (7)	0.0237 (8)	0.0291 (8)	0.0026 (6)	0.0033 (6)	0.0149 (7)
C10A	0.0286 (8)	0.0303 (10)	0.0425 (10)	0.0091 (7)	0.0168 (7)	0.0210 (8)
C11A	0.0359 (9)	0.0386 (11)	0.0513 (11)	0.0054 (8)	0.0198 (8)	0.0297 (10)
C12A	0.0319 (9)	0.0273 (10)	0.0469 (11)	0.0007 (7)	0.0040 (7)	0.0246 (9)
C13A	0.0324 (9)	0.0231 (9)	0.0326 (9)	0.0081 (7)	0.0054 (7)	0.0117 (8)
C14A	0.0251 (8)	0.0283 (9)	0.0297 (8)	0.0061 (6)	0.0076 (6)	0.0166 (7)
N1B	0.0163 (6)	0.0231 (7)	0.0329 (7)	0.0035 (5)	0.0069 (5)	0.0173 (6)
C2B	0.0200 (7)	0.0222 (8)	0.0272 (8)	0.0058 (6)	0.0083 (6)	0.0128 (7)
N2B	0.0171 (7)	0.0340 (8)	0.0410 (8)	0.0071 (6)	0.0069 (6)	0.0264 (7)
N3B	0.0171 (6)	0.0284 (8)	0.0352 (7)	0.0057 (5)	0.0072 (5)	0.0199 (6)
C4B	0.0192 (7)	0.0265 (9)	0.0338 (8)	0.0047 (6)	0.0077 (6)	0.0179 (7)
C4AB	0.0178 (7)	0.0251 (8)	0.0310 (8)	0.0052 (6)	0.0073 (6)	0.0173 (7)
N4B	0.0164 (7)	0.0448 (10)	0.0647 (11)	0.0056 (6)	0.0068 (6)	0.0430 (9)
N5B	0.0186 (6)	0.0242 (7)	0.0302 (7)	0.0042 (5)	0.0071 (5)	0.0159 (6)
C6B	0.0190 (7)	0.0228 (8)	0.0255 (7)	0.0038 (5)	0.0067 (6)	0.0129 (7)
C7B	0.0187 (7)	0.0207 (8)	0.0277 (8)	0.0047 (5)	0.0064 (6)	0.0124 (7)
N7B	0.0181 (7)	0.0344 (9)	0.0517 (9)	0.0028 (6)	0.0030 (6)	0.0318 (8)
N8B	0.0175 (6)	0.0217 (7)	0.0327 (7)	0.0039 (5)	0.0059 (5)	0.0155 (6)
C8AB	0.0190 (7)	0.0201 (8)	0.0262 (8)	0.0036 (5)	0.0061 (6)	0.0122 (6)
C9B	0.0146 (7)	0.0258 (8)	0.0292 (8)	0.0024 (5)	0.0030 (5)	0.0169 (7)
C10B	0.0362 (9)	0.0403 (12)	0.0410 (10)	0.0185 (8)	0.0203 (8)	0.0264 (9)
C11B	0.0443 (11)	0.0681 (16)	0.0625 (13)	0.0231 (10)	0.0306 (10)	0.0523 (13)
C12B	0.0313 (9)	0.0443 (13)	0.0687 (14)	0.0020 (8)	0.0085 (9)	0.0445 (12)
C13B	0.0377 (10)	0.0236 (10)	0.0449 (11)	0.0041 (7)	−0.0004 (8)	0.0156 (9)
C14B	0.0354 (9)	0.0296 (10)	0.0280 (9)	0.0080 (7)	0.0078 (7)	0.0150 (8)
C1C	0.0625 (15)	0.0538 (15)	0.0415 (12)	0.0268 (12)	0.0133 (10)	0.0253 (12)
O1C	0.0324 (6)	0.0601 (9)	0.0575 (8)	0.0117 (6)	0.0153 (6)	0.0454 (8)
S1C	0.0317 (2)	0.0313 (3)	0.0405 (2)	0.00437 (17)	0.00853 (17)	0.0193 (2)
C2C	0.0647 (16)	0.0565 (17)	0.0508 (14)	−0.0176 (12)	0.0254 (12)	0.0181 (13)
C1D	0.0577 (14)	0.0547 (17)	0.0780 (19)	−0.0127 (12)	0.0177 (13)	0.0371 (15)
O1D	0.0384 (7)	0.0419 (8)	0.0659 (9)	0.0097 (6)	0.0200 (6)	0.0378 (7)
S1D	0.0369 (2)	0.0320 (3)	0.0365 (2)	0.00482 (18)	0.00971 (18)	0.0192 (2)
C2D	0.0721 (17)	0.0645 (17)	0.0529 (14)	0.0358 (14)	0.0262 (12)	0.0289 (13)
C1E	0.0242 (7)	0.0229 (8)	0.0273 (8)	0.0032 (6)	0.0083 (6)	0.0127 (7)
O1E	0.0242 (6)	0.0413 (8)	0.0548 (8)	0.0048 (5)	0.0079 (5)	0.0373 (7)
C2E	0.0270 (9)	0.0362 (11)	0.0413 (10)	−0.0026 (7)	0.0050 (7)	0.0240 (9)
O2E	0.0244 (6)	0.0375 (7)	0.0483 (7)	0.0059 (5)	0.0080 (5)	0.0314 (6)
C1F	0.0258 (8)	0.0274 (9)	0.0248 (8)	0.0001 (6)	0.0060 (6)	0.0149 (7)
O1F	0.0233 (5)	0.0395 (7)	0.0494 (7)	0.0042 (5)	0.0069 (5)	0.0323 (6)
C2F	0.0276 (9)	0.0445 (12)	0.0457 (11)	−0.0049 (8)	0.0032 (8)	0.0299 (10)
O2F	0.0260 (6)	0.0387 (8)	0.0601 (8)	0.0066 (5)	0.0119 (5)	0.0336 (7)

Geometric parameters (Å, º)

N1A—C2A	1.3591 (18)	C6B—C7B	1.456 (2)
N1A—C8AA	1.3684 (18)	C6B—C9B	1.491 (2)
N1A—H1XA	0.904 (18)	C7B—N7B	1.3294 (18)
C2A—N2A	1.3130 (19)	C7B—N8B	1.3426 (18)
C2A—N3A	1.3448 (18)	N7B—H6B	0.821 (18)
N2A—H2A	0.870 (19)	N7B—H7B	0.86 (2)
N2A—H3A	0.84 (2)	N8B—C8AB	1.3421 (17)
N3A—C4A	1.3378 (18)	C9B—C10B	1.387 (2)
C4A—N4A	1.3243 (19)	C9B—C14B	1.387 (2)
C4A—C4AA	1.4376 (19)	C10B—C11B	1.376 (3)
N4A—H4A	0.873 (18)	C10B—H10B	0.87 (2)
N4A—H5A	0.848 (19)	C11B—C12B	1.363 (3)
C4AA—N5A	1.3561 (18)	C11B—H11B	0.93 (2)
C4AA—C8AA	1.3896 (19)	C12B—C13B	1.383 (3)
N5A—C6A	1.3171 (17)	C12B—H12B	0.92 (2)
C6A—C7A	1.457 (2)	C13B—C14B	1.387 (2)
C6A—C9A	1.484 (2)	C13B—H13B	0.91 (2)
C7A—N7A	1.3304 (18)	C14B—H14B	0.895 (18)
C7A—N8A	1.3394 (18)	C1C—S1C	1.773 (2)
N7A—H6A	0.832 (17)	C1C—H1C	0.97 (3)
N7A—H7A	0.91 (2)	C1C—H2C	0.91 (2)
N8A—C8AA	1.3416 (17)	C1C—H3C	1.01 (2)
C9A—C14A	1.391 (2)	O1C—S1C	1.5098 (13)
C9A—C10A	1.395 (2)	S1C—C2C	1.774 (2)
C10A—C11A	1.388 (2)	C2C—H4C	0.93 (4)
C10A—H10A	0.924 (17)	C2C—H5C	0.90 (3)
C11A—C12A	1.385 (3)	C2C—H6C	0.95 (3)
C11A—H11A	0.909 (19)	C1D—S1D	1.771 (2)
C12A—C13A	1.376 (3)	C1D—H1D	0.99 (4)
C12A—H12A	0.914 (19)	C1D—H2D	0.91 (3)
C13A—C14A	1.387 (2)	C1D—H3D	0.95 (3)
C13A—H13A	0.838 (18)	O1D—S1D	1.4925 (12)
C14A—H14A	0.941 (17)	S1D—C2D	1.783 (2)
N1B—C2B	1.3620 (18)	C2D—H4D	1.05 (3)
N1B—C8AB	1.3753 (18)	C2D—H5D	0.97 (3)
N1B—H1XB	0.891 (19)	C2D—H6D	0.96 (3)
C2B—N2B	1.3131 (19)	C1E—O2E	1.2447 (17)
C2B—N3B	1.3489 (18)	C1E—O1E	1.2606 (18)
N2B—H2B	0.901 (18)	C1E—C2E	1.512 (2)
N2B—H3B	0.803 (17)	C2E—H1E	0.99 (2)
N3B—C4B	1.3357 (19)	C2E—H2E	1.01 (2)
C4B—N4B	1.3213 (19)	C2E—H3E	0.93 (2)
C4B—C4AB	1.4364 (19)	C1F—O2F	1.2515 (18)
C4AB—N5B	1.3535 (18)	C1F—O1F	1.2588 (18)
C4AB—C8AB	1.3937 (19)	C1F—C2F	1.512 (2)
N4B—H4B	0.809 (19)	C2F—H1F	1.02 (3)
N4B—H5B	0.86 (2)	C2F—H2F	0.87 (3)
N5B—C6B	1.3108 (17)	C2F—H3F	0.91 (3)
C2A—N1A—C8AA	120.19 (12)	N7B—C7B—C6B	120.12 (13)
C2A—N1A—H1XA	117.3 (11)	N8B—C7B—C6B	121.31 (12)
C8AA—N1A—H1XA	122.5 (11)	C7B—N7B—H6B	119.7 (11)
N2A—C2A—N3A	119.34 (13)	C7B—N7B—H7B	120.0 (13)
N2A—C2A—N1A	117.65 (13)	H6B—N7B—H7B	119.0 (17)
N3A—C2A—N1A	123.00 (13)	C8AB—N8B—C7B	116.14 (12)
C2A—N2A—H2A	120.8 (12)	N8B—C8AB—N1B	118.73 (12)
C2A—N2A—H3A	117.9 (13)	N8B—C8AB—C4AB	122.61 (13)
H2A—N2A—H3A	121.4 (18)	N1B—C8AB—C4AB	118.66 (12)
C4A—N3A—C2A	118.56 (11)	C10B—C9B—C14B	118.74 (15)
N4A—C4A—N3A	118.25 (12)	C10B—C9B—C6B	121.17 (15)
N4A—C4A—C4AA	120.36 (13)	C14B—C9B—C6B	119.72 (14)
N3A—C4A—C4AA	121.39 (12)	C11B—C10B—C9B	120.77 (19)
C4A—N4A—H4A	117.9 (11)	C11B—C10B—H10B	122.0 (13)
C4A—N4A—H5A	122.1 (11)	C9B—C10B—H10B	117.2 (13)
H4A—N4A—H5A	120.0 (16)	C12B—C11B—C10B	120.18 (18)
N5A—C4AA—C8AA	121.35 (12)	C12B—C11B—H11B	123.5 (14)
N5A—C4AA—C4A	120.92 (12)	C10B—C11B—H11B	116.2 (14)
C8AA—C4AA—C4A	117.61 (13)	C11B—C12B—C13B	120.33 (17)
C6A—N5A—C4AA	117.82 (12)	C11B—C12B—H12B	120.0 (12)
N5A—C6A—C7A	120.09 (13)	C13B—C12B—H12B	119.7 (12)
N5A—C6A—C9A	117.51 (12)	C12B—C13B—C14B	119.65 (19)
C7A—C6A—C9A	122.35 (12)	C12B—C13B—H13B	120.4 (13)
N7A—C7A—N8A	117.43 (13)	C14B—C13B—H13B	120.0 (13)
N7A—C7A—C6A	121.12 (13)	C13B—C14B—C9B	120.29 (17)
N8A—C7A—C6A	121.45 (12)	C13B—C14B—H14B	121.3 (13)
C7A—N7A—H6A	118.4 (11)	C9B—C14B—H14B	118.4 (13)
C7A—N7A—H7A	116.8 (12)	S1C—C1C—H1C	103.0 (15)
H6A—N7A—H7A	121.1 (16)	S1C—C1C—H2C	109.7 (11)
C7A—N8A—C8AA	116.27 (12)	H1C—C1C—H2C	103.6 (19)
N8A—C8AA—N1A	118.26 (12)	S1C—C1C—H3C	109.7 (13)
N8A—C8AA—C4AA	122.54 (13)	H1C—C1C—H3C	114 (2)
N1A—C8AA—C4AA	119.20 (12)	H2C—C1C—H3C	116.2 (18)
C14A—C9A—C10A	118.84 (15)	O1C—S1C—C1C	104.76 (10)
C14A—C9A—C6A	120.11 (14)	O1C—S1C—C2C	105.07 (10)
C10A—C9A—C6A	120.80 (14)	C1C—S1C—C2C	100.02 (15)
C11A—C10A—C9A	120.55 (17)	S1C—C2C—H4C	114 (2)
C11A—C10A—H10A	120.6 (11)	S1C—C2C—H5C	109.0 (19)
C9A—C10A—H10A	118.8 (10)	H4C—C2C—H5C	105 (3)
C12A—C11A—C10A	119.94 (17)	S1C—C2C—H6C	105.8 (19)
C12A—C11A—H11A	121.4 (13)	H4C—C2C—H6C	111 (3)
C10A—C11A—H11A	118.2 (12)	H5C—C2C—H6C	111 (3)
C13A—C12A—C11A	119.81 (17)	S1D—C1D—H1D	108 (2)
C13A—C12A—H12A	120.1 (11)	S1D—C1D—H2D	108 (2)
C11A—C12A—H12A	120.0 (11)	H1D—C1D—H2D	120 (3)
C12A—C13A—C14A	120.62 (18)	S1D—C1D—H3D	101.4 (17)
C12A—C13A—H13A	118.2 (12)	H1D—C1D—H3D	105 (3)
C14A—C13A—H13A	121.2 (12)	H2D—C1D—H3D	112 (3)
C13A—C14A—C9A	120.20 (16)	O1D—S1D—C1D	105.84 (11)
C13A—C14A—H14A	119.7 (11)	O1D—S1D—C2D	105.48 (10)
C9A—C14A—H14A	120.1 (11)	C1D—S1D—C2D	99.52 (16)
C2B—N1B—C8AB	120.34 (12)	S1D—C2D—H4D	109.8 (17)
C2B—N1B—H1XB	117.0 (11)	S1D—C2D—H5D	109.1 (15)
C8AB—N1B—H1XB	122.6 (11)	H4D—C2D—H5D	110 (2)
N2B—C2B—N3B	119.07 (12)	S1D—C2D—H6D	106.2 (14)
N2B—C2B—N1B	118.05 (13)	H4D—C2D—H6D	113 (2)
N3B—C2B—N1B	122.87 (13)	H5D—C2D—H6D	109 (2)
C2B—N2B—H2B	117.1 (11)	O2E—C1E—O1E	124.82 (14)
C2B—N2B—H3B	120.8 (12)	O2E—C1E—C2E	117.75 (14)
H2B—N2B—H3B	121.7 (16)	O1E—C1E—C2E	117.43 (13)
C4B—N3B—C2B	118.64 (11)	C1E—C2E—H1E	110.8 (13)
N4B—C4B—N3B	118.55 (13)	C1E—C2E—H2E	112.2 (12)
N4B—C4B—C4AB	119.99 (14)	H1E—C2E—H2E	106.0 (18)
N3B—C4B—C4AB	121.46 (13)	C1E—C2E—H3E	111.3 (14)
N5B—C4AB—C8AB	121.31 (12)	H1E—C2E—H3E	113.5 (18)
N5B—C4AB—C4B	120.57 (12)	H2E—C2E—H3E	102.8 (18)
C8AB—C4AB—C4B	118.01 (13)	O2F—C1F—O1F	124.59 (14)
C4B—N4B—H4B	121.9 (13)	O2F—C1F—C2F	117.71 (14)
C4B—N4B—H5B	119.7 (13)	O1F—C1F—C2F	117.69 (14)
H4B—N4B—H5B	118.0 (18)	C1F—C2F—H1F	114.0 (17)
C6B—N5B—C4AB	117.90 (12)	C1F—C2F—H2F	111.9 (19)
N5B—C6B—C7B	120.50 (13)	H1F—C2F—H2F	96 (2)
N5B—C6B—C9B	116.81 (12)	C1F—C2F—H3F	111.3 (16)
C7B—C6B—C9B	122.64 (12)	H1F—C2F—H3F	103 (2)
N7B—C7B—N8B	118.57 (13)	H2F—C2F—H3F	120 (2)
C8AA—N1A—C2A—N2A	−179.95 (14)	C8AB—N1B—C2B—N2B	−178.46 (14)
C8AA—N1A—C2A—N3A	1.0 (2)	C8AB—N1B—C2B—N3B	0.7 (2)
N2A—C2A—N3A—C4A	−179.27 (14)	N2B—C2B—N3B—C4B	177.54 (14)
N1A—C2A—N3A—C4A	−0.2 (2)	N1B—C2B—N3B—C4B	−1.6 (2)
C2A—N3A—C4A—N4A	178.70 (14)	C2B—N3B—C4B—N4B	−178.34 (15)
C2A—N3A—C4A—C4AA	−1.7 (2)	C2B—N3B—C4B—C4AB	1.1 (2)
N4A—C4A—C4AA—N5A	6.2 (2)	N4B—C4B—C4AB—N5B	−4.1 (2)
N3A—C4A—C4AA—N5A	−173.38 (14)	N3B—C4B—C4AB—N5B	176.46 (15)
N4A—C4A—C4AA—C8AA	−177.64 (15)	N4B—C4B—C4AB—C8AB	179.72 (16)
N3A—C4A—C4AA—C8AA	2.7 (2)	N3B—C4B—C4AB—C8AB	0.3 (2)
C8AA—C4AA—N5A—C6A	1.1 (2)	C8AB—C4AB—N5B—C6B	0.3 (2)
C4A—C4AA—N5A—C6A	177.05 (14)	C4B—C4AB—N5B—C6B	−175.72 (14)
C4AA—N5A—C6A—C7A	5.0 (2)	C4AB—N5B—C6B—C7B	−4.2 (2)
C4AA—N5A—C6A—C9A	−172.51 (13)	C4AB—N5B—C6B—C9B	173.13 (13)
N5A—C6A—C7A—N7A	173.77 (14)	N5B—C6B—C7B—N7B	−175.17 (15)
C9A—C6A—C7A—N7A	−8.9 (2)	C9B—C6B—C7B—N7B	7.6 (2)
N5A—C6A—C7A—N8A	−7.0 (2)	N5B—C6B—C7B—N8B	4.9 (2)
C9A—C6A—C7A—N8A	170.31 (14)	C9B—C6B—C7B—N8B	−172.27 (14)
N7A—C7A—N8A—C8AA	−178.38 (14)	N7B—C7B—N8B—C8AB	178.85 (14)
C6A—C7A—N8A—C8AA	2.4 (2)	C6B—C7B—N8B—C8AB	−1.2 (2)
C7A—N8A—C8AA—N1A	−176.25 (13)	C7B—N8B—C8AB—N1B	178.03 (13)
C7A—N8A—C8AA—C4AA	3.8 (2)	C7B—N8B—C8AB—C4AB	−2.7 (2)
C2A—N1A—C8AA—N8A	−179.77 (14)	C2B—N1B—C8AB—N8B	179.99 (14)
C2A—N1A—C8AA—C4AA	0.2 (2)	C2B—N1B—C8AB—C4AB	0.7 (2)
N5A—C4AA—C8AA—N8A	−5.9 (2)	N5B—C4AB—C8AB—N8B	3.4 (2)
C4A—C4AA—C8AA—N8A	178.03 (14)	C4B—C4AB—C8AB—N8B	179.58 (14)
N5A—C4AA—C8AA—N1A	174.17 (13)	N5B—C4AB—C8AB—N1B	−177.33 (13)
C4A—C4AA—C8AA—N1A	−1.9 (2)	C4B—C4AB—C8AB—N1B	−1.2 (2)
N5A—C6A—C9A—C14A	118.55 (16)	N5B—C6B—C9B—C10B	72.73 (19)
C7A—C6A—C9A—C14A	−58.9 (2)	C7B—C6B—C9B—C10B	−109.97 (17)
N5A—C6A—C9A—C10A	−55.58 (19)	N5B—C6B—C9B—C14B	−100.17 (17)
C7A—C6A—C9A—C10A	127.01 (16)	C7B—C6B—C9B—C14B	77.13 (19)
C14A—C9A—C10A—C11A	−0.4 (2)	C14B—C9B—C10B—C11B	1.7 (2)
C6A—C9A—C10A—C11A	173.78 (14)	C6B—C9B—C10B—C11B	−171.24 (15)
C9A—C10A—C11A—C12A	−1.3 (3)	C9B—C10B—C11B—C12B	−0.1 (3)
C10A—C11A—C12A—C13A	1.7 (3)	C10B—C11B—C12B—C13B	−1.4 (3)
C11A—C12A—C13A—C14A	−0.5 (2)	C11B—C12B—C13B—C14B	1.1 (3)
C12A—C13A—C14A—C9A	−1.2 (2)	C12B—C13B—C14B—C9B	0.6 (2)
C10A—C9A—C14A—C13A	1.7 (2)	C10B—C9B—C14B—C13B	−2.0 (2)
C6A—C9A—C14A—C13A	−172.58 (13)	C6B—C9B—C14B—C13B	171.10 (13)

Triamterenium succinate, DMSO solvate (1b_DMSO)

Crystal data

C12H12N7^+·C4H5O4^−·C2H6OS	F(000) = 944
Mr = 449.49	Dx = 1.420 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.5226 (7) Å	Cell parameters from 8640 reflections
b = 14.9966 (7) Å	θ = 1.0–27.5°
c = 10.6958 (5) Å	µ = 0.20 mm^−1
β = 104.179 (2)°	T = 220 K
V = 2102.95 (18) Å^3	Block, colourless
Z = 4	0.18 × 0.10 × 0.07 mm

Data collection

Nonius Kappa CCD diffractometer	4586 independent reflections
Radiation source: fine-focus sealed tube	2099 reflections with I > 2σ(I)
None monochromator	Rint = 0.042
Thin slice ω and φ scans	θmax = 27.4°, θmin = 3.5°
Absorption correction: multi-scan multi-scan from symmetry-related measurements Sortav (Blessing 1995)	h = −14→17
Tmin = 0.841, Tmax = 1.000	k = −19→19
12060 measured reflections	l = −13→13

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.036	Hydrogen site location: difference Fourier map
wR(F^2) = 0.074	All H-atom parameters refined
S = 0.75	w = 1/[σ^2(Fo^2) + (0.0339P)^2] where P = (Fo^2 + 2Fc^2)/3
4586 reflections	(Δ/σ)max = 0.001
372 parameters	Δρmax = 0.31 e Å^−3
0 restraints	Δρmin = −0.31 e Å^−3

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
N1A	1.05320 (10)	0.03264 (9)	0.86586 (13)	0.0326 (4)
C2A	1.08847 (13)	0.11235 (10)	0.91829 (15)	0.0307 (4)
N2A	1.14807 (12)	0.11192 (11)	1.03579 (15)	0.0393 (4)
N3A	1.06604 (10)	0.19013 (8)	0.85559 (12)	0.0333 (4)
C4A	1.00405 (13)	0.18843 (11)	0.73612 (16)	0.0326 (4)
N4A	0.98281 (12)	0.26490 (10)	0.67422 (16)	0.0401 (4)
N5A	0.89096 (10)	0.10676 (8)	0.56186 (13)	0.0334 (4)
C4AA	0.96044 (12)	0.10679 (10)	0.67845 (15)	0.0302 (4)
C6A	0.85157 (12)	0.02958 (10)	0.51569 (15)	0.0317 (4)
C7A	0.88728 (13)	−0.05236 (10)	0.58359 (16)	0.0326 (4)
N7A	0.85642 (13)	−0.13050 (10)	0.53081 (16)	0.0458 (5)
N8A	0.95339 (10)	−0.05201 (8)	0.69967 (13)	0.0327 (4)
C8AA	0.98766 (12)	0.02834 (10)	0.74614 (15)	0.0300 (4)
C9A	0.77068 (13)	0.02975 (10)	0.39273 (16)	0.0313 (4)
C10A	0.78585 (16)	0.07409 (12)	0.28532 (17)	0.0392 (5)
C11A	0.70797 (18)	0.07927 (14)	0.1739 (2)	0.0525 (6)
C12A	0.61483 (18)	0.04069 (14)	0.1687 (2)	0.0548 (6)
C13A	0.59860 (17)	−0.00311 (13)	0.2735 (2)	0.0500 (6)
C14A	0.67612 (15)	−0.00922 (12)	0.38525 (19)	0.0418 (5)
C1B	0.80332 (14)	0.38476 (11)	0.39161 (17)	0.0374 (5)
O1B	0.87992 (9)	0.38466 (7)	0.48458 (11)	0.0427 (3)
C2B	0.60890 (16)	0.32680 (17)	0.1488 (2)	0.0591 (6)
O2B	0.76081 (10)	0.45462 (7)	0.33840 (12)	0.0551 (4)
C3B	0.75909 (16)	0.29521 (12)	0.3403 (2)	0.0470 (6)
O3B	0.63185 (12)	0.41104 (11)	0.13400 (14)	0.0723 (5)
C4B	0.64446 (17)	0.29038 (15)	0.2839 (2)	0.0533 (6)
O4B	0.56016 (13)	0.28359 (11)	0.06050 (15)	0.0947 (6)
C1C	0.3455 (2)	0.30097 (18)	0.4108 (2)	0.0580 (6)
O1C	0.25405 (10)	0.26687 (7)	0.17183 (11)	0.0549 (4)
S1C	0.35932 (4)	0.26335 (3)	0.25988 (4)	0.04554 (16)
C2C	0.3818 (3)	0.14855 (15)	0.2971 (3)	0.0671 (8)
H1XA	1.0747 (13)	−0.0155 (10)	0.9133 (15)	0.045 (5)*
H2A	1.1703 (11)	0.0607 (11)	1.0804 (15)	0.037 (5)*
H3A	1.1697 (11)	0.1595 (10)	1.0683 (14)	0.028 (5)*
H4A	1.0076 (14)	0.3173 (13)	0.7100 (16)	0.064 (7)*
H5A	0.9409 (12)	0.2664 (9)	0.5978 (16)	0.030 (5)*
H6A	0.8141 (12)	−0.1326 (9)	0.4533 (14)	0.030 (5)*
H7A	0.8803 (12)	−0.1756 (10)	0.5695 (15)	0.030 (5)*
H10A	0.8510 (12)	0.1024 (9)	0.2888 (13)	0.029 (5)*
H11A	0.7201 (13)	0.1104 (10)	0.1042 (17)	0.052 (6)*
H12A	0.5610 (13)	0.0459 (10)	0.0920 (17)	0.049 (5)*
H13A	0.5341 (13)	−0.0300 (11)	0.2747 (15)	0.050 (6)*
H14A	0.6665 (12)	−0.0381 (10)	0.4608 (15)	0.042 (5)*
H3B	0.6799 (18)	0.4353 (15)	0.220 (2)	0.100 (8)*
H4B	0.7783 (15)	0.2533 (12)	0.4052 (19)	0.070 (7)*
H5B	0.7945 (16)	0.2741 (14)	0.270 (2)	0.092 (8)*
H6B	0.6231 (13)	0.2256 (12)	0.2839 (16)	0.059 (6)*
H7B	0.6127 (13)	0.3238 (12)	0.3415 (16)	0.055 (6)*
H1C	0.3244 (15)	0.3661 (14)	0.4007 (18)	0.079 (7)*
H2C	0.4089 (15)	0.2949 (12)	0.4736 (19)	0.068 (7)*
H3C	0.2979 (17)	0.2615 (13)	0.435 (2)	0.089 (9)*
H4C	0.3868 (18)	0.1228 (15)	0.217 (2)	0.108 (10)*
H5C	0.317 (2)	0.1314 (18)	0.328 (3)	0.142 (13)*
H6C	0.4362 (14)	0.1461 (11)	0.3578 (18)	0.052 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0367 (9)	0.0225 (8)	0.0326 (9)	0.0029 (7)	−0.0030 (7)	0.0021 (7)
C2A	0.0320 (11)	0.0267 (10)	0.0305 (10)	−0.0008 (8)	0.0020 (9)	−0.0022 (8)
N2A	0.0503 (11)	0.0228 (9)	0.0358 (10)	−0.0028 (8)	−0.0069 (8)	0.0002 (8)
N3A	0.0369 (9)	0.0257 (8)	0.0321 (9)	−0.0005 (7)	−0.0016 (7)	0.0021 (7)
C4A	0.0318 (11)	0.0277 (10)	0.0358 (11)	0.0025 (8)	0.0035 (9)	0.0013 (8)
N4A	0.0479 (11)	0.0257 (9)	0.0359 (10)	−0.0028 (8)	−0.0103 (8)	0.0035 (8)
N5A	0.0356 (9)	0.0267 (8)	0.0350 (9)	−0.0004 (7)	0.0028 (7)	0.0019 (7)
C4AA	0.0316 (11)	0.0240 (9)	0.0305 (10)	−0.0012 (8)	−0.0008 (9)	−0.0008 (8)
C6A	0.0318 (11)	0.0291 (10)	0.0318 (10)	0.0005 (8)	0.0033 (8)	0.0006 (8)
C7A	0.0344 (11)	0.0236 (9)	0.0359 (11)	−0.0005 (8)	0.0016 (9)	−0.0008 (8)
N7A	0.0571 (12)	0.0274 (10)	0.0378 (11)	0.0015 (8)	−0.0172 (9)	0.0028 (8)
N8A	0.0356 (9)	0.0242 (8)	0.0334 (9)	−0.0011 (6)	−0.0009 (7)	−0.0020 (6)
C8AA	0.0289 (10)	0.0290 (10)	0.0296 (10)	−0.0005 (8)	0.0024 (8)	−0.0003 (8)
C9A	0.0323 (11)	0.0230 (9)	0.0351 (11)	0.0038 (8)	0.0016 (9)	−0.0063 (8)
C10A	0.0375 (13)	0.0410 (11)	0.0372 (12)	0.0021 (10)	0.0053 (10)	0.0011 (9)
C11A	0.0620 (17)	0.0572 (14)	0.0353 (13)	0.0094 (12)	0.0060 (12)	0.0059 (11)
C12A	0.0501 (16)	0.0543 (14)	0.0454 (14)	0.0098 (12)	−0.0164 (13)	−0.0076 (11)
C13A	0.0353 (14)	0.0401 (12)	0.0674 (16)	−0.0030 (10)	−0.0010 (12)	−0.0050 (11)
C14A	0.0395 (13)	0.0376 (11)	0.0433 (13)	−0.0007 (9)	0.0006 (11)	0.0052 (10)
C1B	0.0398 (12)	0.0333 (11)	0.0370 (11)	−0.0002 (9)	0.0053 (10)	−0.0016 (9)
O1B	0.0424 (8)	0.0343 (7)	0.0422 (7)	−0.0009 (6)	−0.0070 (7)	−0.0038 (6)
C2B	0.0435 (14)	0.0720 (16)	0.0529 (15)	0.0039 (12)	−0.0056 (11)	−0.0086 (13)
O2B	0.0616 (9)	0.0306 (7)	0.0570 (9)	0.0035 (7)	−0.0161 (7)	0.0035 (6)
C3B	0.0465 (15)	0.0329 (11)	0.0504 (14)	−0.0031 (10)	−0.0093 (12)	−0.0004 (10)
O3B	0.0762 (12)	0.0748 (11)	0.0504 (10)	−0.0063 (9)	−0.0145 (8)	0.0141 (8)
C4B	0.0525 (16)	0.0462 (14)	0.0570 (16)	−0.0077 (11)	0.0056 (13)	−0.0050 (12)
O4B	0.0835 (12)	0.1100 (13)	0.0661 (11)	−0.0097 (10)	−0.0287 (9)	−0.0246 (9)
C1C	0.0586 (18)	0.0685 (18)	0.0402 (14)	0.0049 (14)	−0.0010 (13)	−0.0083 (12)
O1C	0.0622 (9)	0.0398 (7)	0.0451 (8)	0.0018 (6)	−0.0205 (7)	0.0014 (6)
S1C	0.0485 (3)	0.0447 (3)	0.0393 (3)	−0.0007 (3)	0.0027 (2)	0.0008 (2)
C2C	0.077 (2)	0.0519 (14)	0.0570 (17)	0.0219 (14)	−0.0128 (17)	0.0037 (13)

Geometric parameters (Å, º)

N1A—C2A	1.3564 (18)	C11A—H11A	0.928 (17)
N1A—C8AA	1.3687 (19)	C12A—C13A	1.363 (3)
N1A—H1XA	0.889 (16)	C12A—H12A	0.957 (17)
C2A—N2A	1.316 (2)	C13A—C14A	1.386 (3)
C2A—N3A	1.3427 (18)	C13A—H13A	0.964 (17)
N2A—H2A	0.915 (16)	C14A—H14A	0.953 (16)
N2A—H3A	0.816 (15)	C1B—O1B	1.2479 (19)
N3A—C4A	1.346 (2)	C1B—O2B	1.2616 (18)
C4A—N4A	1.320 (2)	C1B—C3B	1.517 (2)
C4A—C4AA	1.431 (2)	C2B—O4B	1.201 (2)
N4A—H4A	0.901 (19)	C2B—O3B	1.320 (2)
N4A—H5A	0.873 (16)	C2B—C4B	1.509 (3)
N5A—C6A	1.3185 (18)	C3B—C4B	1.521 (3)
N5A—C4AA	1.3653 (18)	C3B—H4B	0.925 (19)
C4AA—C8AA	1.383 (2)	C3B—H5B	1.03 (2)
C6A—C7A	1.449 (2)	O3B—H3B	1.05 (2)
C6A—C9A	1.490 (2)	C4B—H6B	1.014 (17)
C7A—N7A	1.323 (2)	C4B—H7B	0.973 (17)
C7A—N8A	1.3406 (18)	C1C—S1C	1.763 (2)
N7A—H6A	0.885 (15)	C1C—H1C	1.02 (2)
N7A—H7A	0.816 (15)	C1C—H2C	0.96 (2)
N8A—C8AA	1.3420 (19)	C1C—H3C	0.95 (2)
C9A—C10A	1.385 (2)	O1C—S1C	1.5031 (12)
C9A—C14A	1.390 (2)	S1C—C2C	1.776 (2)
C10A—C11A	1.386 (2)	C2C—H4C	0.96 (2)
C10A—H10A	0.971 (15)	C2C—H5C	1.04 (3)
C11A—C12A	1.375 (3)	C2C—H6C	0.855 (18)
C2A—N1A—C8AA	120.66 (14)	C13A—C12A—H12A	120.2 (10)
C2A—N1A—H1XA	116.5 (10)	C11A—C12A—H12A	119.8 (10)
C8AA—N1A—H1XA	122.8 (10)	C12A—C13A—C14A	120.1 (2)
N2A—C2A—N3A	119.46 (15)	C12A—C13A—H13A	122.7 (10)
N2A—C2A—N1A	117.48 (15)	C14A—C13A—H13A	117.2 (10)
N3A—C2A—N1A	123.06 (14)	C13A—C14A—C9A	120.8 (2)
C2A—N2A—H2A	123.2 (9)	C13A—C14A—H14A	121.9 (10)
C2A—N2A—H3A	118.3 (10)	C9A—C14A—H14A	117.2 (10)
H2A—N2A—H3A	118.3 (14)	O1B—C1B—O2B	123.92 (15)
C2A—N3A—C4A	118.02 (13)	O1B—C1B—C3B	117.65 (16)
N4A—C4A—N3A	117.92 (15)	O2B—C1B—C3B	118.43 (16)
N4A—C4A—C4AA	120.72 (16)	O4B—C2B—O3B	121.5 (2)
N3A—C4A—C4AA	121.35 (14)	O4B—C2B—C4B	122.9 (2)
C4A—N4A—H4A	122.1 (11)	O3B—C2B—C4B	115.61 (18)
C4A—N4A—H5A	120.2 (9)	C1B—C3B—C4B	117.31 (17)
H4A—N4A—H5A	117.6 (15)	C1B—C3B—H4B	108.4 (11)
C6A—N5A—C4AA	117.83 (13)	C4B—C3B—H4B	109.7 (13)
N5A—C4AA—C8AA	120.87 (14)	C1B—C3B—H5B	108.8 (12)
N5A—C4AA—C4A	120.84 (14)	C4B—C3B—H5B	107.8 (12)
C8AA—C4AA—C4A	118.25 (15)	H4B—C3B—H5B	104.0 (17)
N5A—C6A—C7A	120.16 (14)	C2B—O3B—H3B	109.9 (12)
N5A—C6A—C9A	118.09 (14)	C2B—C4B—C3B	114.66 (19)
C7A—C6A—C9A	121.75 (14)	C2B—C4B—H6B	108.9 (9)
N7A—C7A—N8A	117.88 (15)	C3B—C4B—H6B	108.0 (10)
N7A—C7A—C6A	120.39 (15)	C2B—C4B—H7B	109.5 (10)
N8A—C7A—C6A	121.72 (14)	C3B—C4B—H7B	106.9 (11)
C7A—N7A—H6A	119.7 (9)	H6B—C4B—H7B	108.8 (15)
C7A—N7A—H7A	118.2 (11)	S1C—C1C—H1C	107.5 (11)
H6A—N7A—H7A	121.9 (14)	S1C—C1C—H2C	109.6 (12)
C7A—N8A—C8AA	115.97 (14)	H1C—C1C—H2C	110.2 (15)
N8A—C8AA—N1A	118.33 (14)	S1C—C1C—H3C	106.1 (13)
N8A—C8AA—C4AA	123.13 (15)	H1C—C1C—H3C	115.8 (18)
N1A—C8AA—C4AA	118.55 (15)	H2C—C1C—H3C	107.5 (18)
C10A—C9A—C14A	118.35 (17)	O1C—S1C—C1C	105.42 (11)
C10A—C9A—C6A	120.45 (16)	O1C—S1C—C2C	104.95 (11)
C14A—C9A—C6A	121.06 (16)	C1C—S1C—C2C	98.96 (14)
C9A—C10A—C11A	120.3 (2)	S1C—C2C—H4C	103.5 (13)
C9A—C10A—H10A	119.7 (9)	S1C—C2C—H5C	101.6 (15)
C11A—C10A—H10A	120.0 (9)	H4C—C2C—H5C	116 (2)
C12A—C11A—C10A	120.5 (2)	S1C—C2C—H6C	106.2 (12)
C12A—C11A—H11A	121.3 (11)	H4C—C2C—H6C	115 (2)
C10A—C11A—H11A	118.2 (11)	H5C—C2C—H6C	112 (2)
C13A—C12A—C11A	120.0 (2)
C8AA—N1A—C2A—N2A	177.39 (16)	C2A—N1A—C8AA—C4AA	1.7 (2)
C8AA—N1A—C2A—N3A	−3.2 (3)	N5A—C4AA—C8AA—N8A	4.2 (3)
N2A—C2A—N3A—C4A	−179.32 (16)	C4A—C4AA—C8AA—N8A	−178.22 (16)
N1A—C2A—N3A—C4A	1.3 (2)	N5A—C4AA—C8AA—N1A	−176.31 (15)
C2A—N3A—C4A—N4A	−179.43 (15)	C4A—C4AA—C8AA—N1A	1.3 (2)
C2A—N3A—C4A—C4AA	1.9 (3)	N5A—C6A—C9A—C10A	51.1 (2)
C6A—N5A—C4AA—C8AA	−0.6 (2)	C7A—C6A—C9A—C10A	−128.59 (18)
C6A—N5A—C4AA—C4A	−178.17 (15)	N5A—C6A—C9A—C14A	−124.59 (17)
N4A—C4A—C4AA—N5A	−4.2 (3)	C7A—C6A—C9A—C14A	55.7 (2)
N3A—C4A—C4AA—N5A	174.40 (15)	C14A—C9A—C10A—C11A	0.2 (3)
N4A—C4A—C4AA—C8AA	178.17 (16)	C6A—C9A—C10A—C11A	−175.59 (16)
N3A—C4A—C4AA—C8AA	−3.2 (3)	C9A—C10A—C11A—C12A	0.1 (3)
C4AA—N5A—C6A—C7A	−4.3 (2)	C10A—C11A—C12A—C13A	−0.1 (3)
C4AA—N5A—C6A—C9A	176.04 (15)	C11A—C12A—C13A—C14A	−0.4 (3)
N5A—C6A—C7A—N7A	−172.47 (17)	C12A—C13A—C14A—C9A	0.7 (3)
C9A—C6A—C7A—N7A	7.2 (3)	C10A—C9A—C14A—C13A	−0.6 (3)
N5A—C6A—C7A—N8A	6.3 (2)	C6A—C9A—C14A—C13A	175.15 (16)
C9A—C6A—C7A—N8A	−174.02 (16)	O1B—C1B—C3B—C4B	148.26 (19)
N7A—C7A—N8A—C8AA	175.97 (16)	O2B—C1B—C3B—C4B	−31.6 (3)
C6A—C7A—N8A—C8AA	−2.8 (2)	O4B—C2B—C4B—C3B	123.5 (2)
C7A—N8A—C8AA—N1A	178.26 (15)	O3B—C2B—C4B—C3B	−58.8 (3)
C7A—N8A—C8AA—C4AA	−2.2 (2)	C1B—C3B—C4B—C2B	78.5 (3)
C2A—N1A—C8AA—N8A	−178.70 (15)

Triamterenium adipate, DMSO solvate (1c_DMSO)

Crystal data

2(C12H12N7)·C6H8O4·2(C2H6OS)	Z = 2
Mr = 808.95	F(000) = 852
Triclinic, P1	Dx = 1.414 Mg m^−3
a = 11.0286 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.7429 (4) Å	Cell parameters from 40707 reflections
c = 14.9742 (5) Å	θ = 1.0–25.4°
α = 115.247 (2)°	µ = 0.21 mm^−1
β = 109.951 (4)°	T = 180 K
γ = 90.122 (2)°	Block, colourless
V = 1900.24 (11) Å^3	0.12 × 0.05 × 0.02 mm

Data collection

Nonius Kappa CCD diffractometer	6951 independent reflections
Radiation source: sealed X-ray tube	5118 reflections with I > 2σ(I)
None monochromator	Rint = 0.052
Thin slice ω and φ scans	θmax = 25.4°, θmin = 3.6°
Absorption correction: multi-scan multi-scan from symmetry-related measurements Sortav (Blessing 1995)	h = −13→12
Tmin = 0.894, Tmax = 1.000	k = −16→16
25204 measured reflections	l = −18→18

Refinement

Refinement on F^2	Primary atom site location: difference Fourier map
Least-squares matrix: full	Secondary atom site location: structure-invariant direct methods
R[F^2 > 2σ(F^2)] = 0.073	Hydrogen site location: mixed
wR(F^2) = 0.191	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0749P)^2 + 4.0839P] where P = (Fo^2 + 2Fc^2)/3
6951 reflections	(Δ/σ)max < 0.001
520 parameters	Δρmax = 1.61 e Å^−3
18 restraints	Δρmin = −0.66 e Å^−3

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)
N1A	0.3191 (3)	0.2248 (2)	0.1399 (2)	0.0278 (6)
C2A	0.2342 (3)	0.2886 (3)	0.1739 (3)	0.0282 (7)
N2A	0.2583 (3)	0.3930 (2)	0.1995 (3)	0.0369 (7)
H3A	0.2043	0.4363	0.2202	0.044*
H2A	0.3282	0.4194	0.1959	0.044*
N3A	0.1270 (3)	0.2501 (2)	0.1800 (2)	0.0287 (6)
C4A	0.1028 (3)	0.1430 (3)	0.1529 (3)	0.0263 (7)
C4AA	0.1927 (3)	0.0729 (3)	0.1223 (3)	0.0258 (7)
N4A	−0.0044 (3)	0.1035 (2)	0.1547 (2)	0.0316 (7)
H4A	−0.0593	0.1469	0.1734	0.038*
H5A	−0.0214	0.0338	0.1371	0.038*
N5A	0.1757 (3)	−0.0320 (2)	0.1071 (2)	0.0276 (6)
C6A	0.2613 (3)	−0.0922 (3)	0.0799 (3)	0.0268 (7)
C7A	0.3626 (3)	−0.0504 (3)	0.0571 (3)	0.0283 (7)
N7A	0.4380 (3)	−0.1160 (3)	0.0157 (3)	0.0350 (7)
N8A	0.3825 (3)	0.0542 (2)	0.0770 (2)	0.0277 (6)
C8AA	0.2991 (3)	0.1156 (3)	0.1126 (3)	0.0259 (7)
C9A	0.2507 (3)	−0.2024 (3)	0.0749 (3)	0.0281 (7)
C10A	0.1383 (4)	−0.2807 (3)	0.0047 (3)	0.0355 (8)
H10A	0.0702	−0.2657	−0.0446	0.043*
C11A	0.1248 (4)	−0.3801 (3)	0.0059 (3)	0.0410 (9)
H11A	0.0489	−0.4338	−0.0435	0.049*
C12A	0.2224 (4)	−0.4008 (3)	0.0793 (3)	0.0403 (9)
H12A	0.2123	−0.4684	0.0815	0.048*
C13A	0.3342 (4)	−0.3244 (3)	0.1494 (3)	0.0340 (8)*
H13A	0.4008	−0.3392	0.1997	0.041*
C14A	0.3494 (4)	−0.2254 (3)	0.1465 (3)	0.0319 (8)*
H14A	0.4276	−0.1735	0.1935	0.038*
N1B	0.3412 (3)	0.7274 (2)	0.6746 (2)	0.0264 (6)
C2B	0.2728 (3)	0.7927 (3)	0.7304 (3)	0.0271 (7)
N2B	0.3006 (3)	0.8988 (2)	0.7636 (2)	0.0330 (7)
H3B	0.2578	0.9436	0.7988	0.040*
H2B	0.3621	0.9248	0.7505	0.040*
N3B	0.1786 (3)	0.7550 (2)	0.7514 (2)	0.0283 (6)
C4B	0.1492 (3)	0.6471 (3)	0.7147 (3)	0.0296 (8)
N4B	0.0531 (3)	0.6080 (2)	0.7311 (3)	0.0379 (8)
H4B	0.0098	0.6530	0.7657	0.045*
H5B	0.0325	0.5372	0.7074	0.045*
C4AB	0.2170 (3)	0.5734 (3)	0.6559 (3)	0.0272 (7)
N5B	0.1853 (3)	0.4641 (2)	0.6194 (2)	0.0279 (6)
C6B	0.2464 (3)	0.3995 (3)	0.5629 (3)	0.0256 (7)
C7B	0.3414 (3)	0.4440 (3)	0.5364 (3)	0.0271 (7)
N7B	0.3961 (3)	0.3771 (3)	0.4725 (3)	0.0364 (8)
N8B	0.3748 (3)	0.5520 (2)	0.5745 (2)	0.0280 (6)
C8AB	0.3126 (3)	0.6159 (3)	0.6349 (3)	0.0259 (7)
C9B	0.2127 (3)	0.2808 (3)	0.5274 (3)	0.0282 (7)
C10B	0.1146 (4)	0.2160 (3)	0.4304 (3)	0.0401 (9)
H10B	0.0752	0.2456	0.3826	0.048*
C11B	0.0728 (4)	0.1076 (3)	0.4016 (3)	0.0463 (10)
H11B	0.0047	0.0636	0.3346	0.056*
C12B	0.1299 (4)	0.0642 (3)	0.4700 (3)	0.0445 (10)
H12B	0.0998	−0.0094	0.4511	0.053*
C13B	0.2306 (4)	0.1272 (3)	0.5659 (3)	0.0451 (10)
H13B	0.2719	0.0961	0.6119	0.054*
C14B	0.2724 (4)	0.2355 (3)	0.5957 (3)	0.0382 (9)
H14B	0.3413	0.2789	0.6624	0.046*
C1C	0.4875 (3)	0.0816 (3)	0.3554 (3)	0.0288 (8)
O1C	0.4799 (3)	0.17533 (19)	0.3599 (2)	0.0354 (6)
C2C	0.3924 (4)	0.0374 (3)	0.3879 (3)	0.0330 (8)
H1C	0.3144	−0.0076	0.3230	0.040*
H2C	0.3629	0.0998	0.4349	0.040*
O2C	0.5644 (3)	0.0226 (2)	0.3227 (2)	0.0423 (7)
C3C	0.4463 (4)	−0.0317 (3)	0.4457 (3)	0.0334 (8)
H3C	0.3735	−0.0649	0.4537	0.040*
H4C	0.4806	−0.0919	0.4007	0.040*
C1D	0.5282 (3)	0.4207 (3)	0.1422 (3)	0.0270 (7)
O1D	0.5016 (3)	0.31838 (19)	0.1063 (2)	0.0367 (6)
C2D	0.6224 (3)	0.4627 (3)	0.1068 (3)	0.0313 (8)
H1D	0.6495	0.3996	0.0582	0.038*
H2D	0.7018	0.5078	0.1700	0.038*
O2D	0.4832 (2)	0.48912 (19)	0.2044 (2)	0.0340 (6)
C3D	0.5618 (3)	0.5307 (3)	0.0497 (3)	0.0302 (8)
H3D	0.5405	0.5964	0.1001	0.036*
H4D	0.6276	0.5558	0.0292	0.036*
S1E	0.16128 (11)	0.67740 (8)	0.32485 (8)	0.0452 (3)
O1E	0.0858 (3)	0.5633 (2)	0.2590 (2)	0.0462 (7)
C1E	0.3249 (4)	0.6647 (4)	0.3889 (3)	0.0499 (11)
H1E	0.3640	0.6302	0.3355	0.075*
H2E	0.3245	0.6197	0.4249	0.075*
H3E	0.3764	0.7374	0.4414	0.075*
C2E	0.1180 (6)	0.7352 (4)	0.4396 (4)	0.0682 (14)
H4E	0.0298	0.7530	0.4194	0.102*
H5E	0.1808	0.8019	0.4944	0.102*
H6E	0.1197	0.6825	0.4678	0.102*
S1F	0.14448 (15)	1.14703 (12)	0.80626 (12)	0.0427 (4)	0.7
O1F	0.1590 (7)	1.0752 (4)	0.8691 (4)	0.0483 (6)*	0.7
C1F	0.3122 (6)	1.1906 (6)	0.8335 (6)	0.0483 (6)*	0.7
H1F	0.3486	1.1276	0.7968	0.072*	0.7
H2F	0.3626	1.2232	0.9105	0.072*	0.7
H3F	0.3169	1.2449	0.8080	0.072*	0.7
C2F	0.1117 (6)	1.2723 (5)	0.8905 (5)	0.0483 (6)*	0.7
H4F	0.0242	1.2606	0.8907	0.072*	0.7
H5F	0.1158	1.3259	0.8641	0.072*	0.7
H6F	0.1771	1.2996	0.9632	0.072*	0.7
S1F'	0.1649 (4)	1.1878 (3)	0.8959 (3)	0.0483 (6)*	0.3
O1F'	0.1441 (15)	1.0650 (9)	0.8489 (10)	0.0483 (6)*	0.3
C1F'	0.2704 (13)	1.2054 (13)	0.8312 (13)	0.0483 (6)*	0.3
H1F'	0.3623	1.2164	0.8775	0.072*	0.3
H2F'	0.2544	1.2692	0.8182	0.072*	0.3
H3F'	0.2513	1.1401	0.7632	0.072*	0.3
C2F'	0.0143 (12)	1.1951 (12)	0.8031 (11)	0.0483 (6)*	0.3
H4F'	−0.0590	1.1512	0.7995	0.072*	0.3
H5F'	0.0187	1.1667	0.7323	0.072*	0.3
H6F'	0.0014	1.2713	0.8271	0.072*	0.3
H1XA	0.375 (4)	0.253 (3)	0.128 (3)	0.038 (11)*
H1XB	0.410 (5)	0.761 (4)	0.670 (4)	0.075 (16)*
H6A	0.422 (4)	−0.184 (3)	−0.006 (3)	0.029 (10)*
H7A	0.489 (4)	−0.091 (4)	−0.001 (3)	0.043 (12)*
H6B	0.381 (4)	0.310 (3)	0.453 (3)	0.032 (10)*
H7B	0.455 (5)	0.403 (4)	0.458 (3)	0.047 (12)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0299 (16)	0.0246 (15)	0.0392 (17)	0.0094 (13)	0.0233 (14)	0.0155 (13)
C2A	0.0316 (19)	0.0280 (18)	0.0313 (18)	0.0084 (15)	0.0181 (15)	0.0141 (15)
N2A	0.0388 (18)	0.0267 (16)	0.061 (2)	0.0150 (13)	0.0350 (16)	0.0208 (15)
N3A	0.0303 (16)	0.0265 (15)	0.0374 (16)	0.0096 (12)	0.0204 (13)	0.0158 (13)
C4A	0.0281 (18)	0.0277 (18)	0.0268 (17)	0.0066 (14)	0.0148 (14)	0.0121 (14)
C4AA	0.0276 (18)	0.0247 (17)	0.0303 (18)	0.0078 (14)	0.0164 (15)	0.0128 (14)
N4A	0.0302 (16)	0.0244 (15)	0.0457 (18)	0.0093 (12)	0.0239 (14)	0.0134 (13)
N5A	0.0294 (15)	0.0281 (15)	0.0288 (15)	0.0082 (12)	0.0158 (12)	0.0124 (12)
C6A	0.0277 (18)	0.0280 (18)	0.0295 (17)	0.0092 (14)	0.0162 (14)	0.0133 (14)
C7A	0.0297 (18)	0.0300 (18)	0.0312 (18)	0.0108 (15)	0.0171 (15)	0.0148 (15)
N7A	0.043 (2)	0.0251 (18)	0.054 (2)	0.0145 (15)	0.0350 (17)	0.0202 (16)
N8A	0.0307 (16)	0.0271 (15)	0.0355 (16)	0.0125 (12)	0.0213 (13)	0.0163 (13)
C8AA	0.0310 (18)	0.0265 (17)	0.0249 (17)	0.0092 (14)	0.0146 (14)	0.0128 (14)
C9A	0.0321 (19)	0.0260 (17)	0.0334 (18)	0.0111 (15)	0.0217 (15)	0.0126 (15)
C10A	0.035 (2)	0.032 (2)	0.041 (2)	0.0081 (16)	0.0169 (17)	0.0165 (17)
C11A	0.039 (2)	0.033 (2)	0.052 (2)	0.0033 (17)	0.0225 (19)	0.0157 (18)
C12A	0.058 (3)	0.032 (2)	0.055 (2)	0.0204 (19)	0.041 (2)	0.0258 (19)
N1B	0.0276 (15)	0.0230 (15)	0.0342 (16)	0.0072 (12)	0.0196 (13)	0.0118 (12)
C2B	0.0265 (18)	0.0278 (18)	0.0287 (17)	0.0066 (14)	0.0129 (14)	0.0125 (15)
N2B	0.0349 (17)	0.0242 (15)	0.0496 (19)	0.0095 (13)	0.0291 (15)	0.0153 (14)
N3B	0.0300 (16)	0.0255 (15)	0.0363 (16)	0.0089 (12)	0.0211 (13)	0.0134 (13)
C4B	0.0313 (19)	0.0292 (18)	0.0346 (19)	0.0084 (15)	0.0186 (15)	0.0151 (15)
N4B	0.0435 (19)	0.0254 (15)	0.056 (2)	0.0101 (14)	0.0366 (16)	0.0147 (15)
C4AB	0.0280 (18)	0.0257 (17)	0.0304 (18)	0.0062 (14)	0.0151 (15)	0.0119 (14)
N5B	0.0278 (15)	0.0292 (15)	0.0311 (15)	0.0084 (12)	0.0159 (13)	0.0140 (13)
C6B	0.0269 (18)	0.0267 (17)	0.0253 (17)	0.0077 (14)	0.0128 (14)	0.0115 (14)
C7B	0.0287 (18)	0.0276 (18)	0.0293 (18)	0.0090 (14)	0.0151 (15)	0.0135 (15)
N7B	0.046 (2)	0.0232 (17)	0.051 (2)	0.0094 (15)	0.0352 (17)	0.0143 (15)
N8B	0.0316 (16)	0.0256 (15)	0.0334 (16)	0.0089 (12)	0.0198 (13)	0.0135 (13)
C8AB	0.0274 (18)	0.0260 (17)	0.0287 (17)	0.0077 (14)	0.0138 (14)	0.0139 (14)
C9B	0.0292 (18)	0.0291 (18)	0.0344 (19)	0.0099 (15)	0.0212 (15)	0.0144 (15)
C10B	0.044 (2)	0.031 (2)	0.040 (2)	0.0079 (17)	0.0113 (18)	0.0151 (17)
C11B	0.042 (2)	0.032 (2)	0.049 (2)	0.0002 (18)	0.0130 (19)	0.0084 (19)
C12B	0.054 (3)	0.028 (2)	0.057 (3)	0.0044 (18)	0.034 (2)	0.0143 (19)
C13B	0.064 (3)	0.040 (2)	0.053 (3)	0.020 (2)	0.035 (2)	0.030 (2)
C14B	0.047 (2)	0.032 (2)	0.036 (2)	0.0085 (17)	0.0175 (18)	0.0151 (17)
C1C	0.0337 (19)	0.0277 (18)	0.0266 (17)	0.0048 (15)	0.0130 (15)	0.0127 (15)
O1C	0.0431 (15)	0.0259 (13)	0.0465 (15)	0.0090 (11)	0.0287 (13)	0.0155 (11)
C2C	0.035 (2)	0.0343 (19)	0.036 (2)	0.0075 (16)	0.0185 (16)	0.0182 (16)
O2C	0.0560 (17)	0.0357 (15)	0.0599 (18)	0.0208 (13)	0.0414 (15)	0.0281 (13)
C3C	0.042 (2)	0.0291 (18)	0.037 (2)	0.0054 (16)	0.0221 (17)	0.0164 (16)
C1D	0.0278 (18)	0.0317 (19)	0.0301 (18)	0.0107 (15)	0.0149 (15)	0.0184 (15)
O1D	0.0436 (15)	0.0266 (13)	0.0511 (16)	0.0111 (11)	0.0320 (13)	0.0166 (12)
C2D	0.0308 (19)	0.0354 (19)	0.0368 (19)	0.0095 (15)	0.0190 (16)	0.0195 (16)
O2D	0.0415 (15)	0.0295 (13)	0.0426 (14)	0.0108 (11)	0.0271 (12)	0.0179 (11)
C3D	0.035 (2)	0.0278 (18)	0.0343 (19)	0.0057 (15)	0.0177 (16)	0.0157 (15)
S1E	0.0561 (7)	0.0367 (6)	0.0458 (6)	0.0063 (5)	0.0233 (5)	0.0183 (5)
O1E	0.0465 (17)	0.0378 (15)	0.0500 (17)	0.0009 (13)	0.0221 (14)	0.0132 (13)
C1E	0.048 (3)	0.048 (3)	0.046 (2)	0.002 (2)	0.016 (2)	0.017 (2)
C2E	0.079 (4)	0.068 (3)	0.055 (3)	0.023 (3)	0.038 (3)	0.016 (3)
S1F	0.0437 (8)	0.0373 (8)	0.0445 (8)	0.0036 (6)	0.0184 (7)	0.0150 (6)

Geometric parameters (Å, º)

N1A—C2A	1.361 (4)	C9B—C14B	1.398 (5)
N1A—C8AA	1.372 (4)	C10B—C11B	1.389 (5)
N1A—H1XA	0.83 (4)	C10B—H10B	0.9500
C2A—N2A	1.317 (4)	C11B—C12B	1.373 (6)
C2A—N3A	1.341 (4)	C11B—H11B	0.9500
N2A—H3A	0.8800	C12B—C13B	1.376 (6)
N2A—H2A	0.8800	C12B—H12B	0.9500
N3A—C4A	1.348 (4)	C13B—C14B	1.385 (5)
C4A—N4A	1.314 (4)	C13B—H13B	0.9500
C4A—C4AA	1.435 (4)	C14B—H14B	0.9500
C4AA—N5A	1.362 (4)	C1C—O2C	1.251 (4)
C4AA—C8AA	1.389 (5)	C1C—O1C	1.266 (4)
N4A—H4A	0.8800	C1C—C2C	1.518 (5)
N4A—H5A	0.8800	C2C—C3C	1.534 (5)
N5A—C6A	1.311 (4)	C2C—H1C	0.9900
C6A—C7A	1.455 (5)	C2C—H2C	0.9900
C6A—C9A	1.487 (5)	C3C—C3C^i	1.510 (7)
C7A—N7A	1.329 (4)	C3C—H3C	0.9900
C7A—N8A	1.339 (4)	C3C—H4C	0.9900
N7A—H6A	0.84 (4)	C1D—O2D	1.253 (4)
N7A—H7A	0.81 (5)	C1D—O1D	1.265 (4)
N8A—C8AA	1.340 (4)	C1D—C2D	1.525 (5)
C9A—C14A	1.389 (5)	C2D—C3D	1.532 (5)
C9A—C10A	1.393 (5)	C2D—H1D	0.9900
C10A—C11A	1.381 (5)	C2D—H2D	0.9900
C10A—H10A	0.9500	C3D—C3D^ii	1.525 (7)
C11A—C12A	1.383 (6)	C3D—H3D	0.9900
C11A—H11A	0.9500	C3D—H4D	0.9900
C12A—C13A	1.376 (6)	S1E—O1E	1.497 (3)
C12A—H12A	0.9500	S1E—C1E	1.780 (4)
C13A—C14A	1.391 (5)	S1E—C2E	1.791 (5)
C13A—H13A	0.9500	C1E—H1E	0.9800
C14A—H14A	0.9500	C1E—H2E	0.9800
N1B—C2B	1.367 (4)	C1E—H3E	0.9800
N1B—C8AB	1.376 (4)	C2E—H4E	0.9800
N1B—H1XB	0.92 (6)	C2E—H5E	0.9800
C2B—N2B	1.321 (4)	C2E—H6E	0.9800
C2B—N3B	1.345 (4)	S1F—O1F	1.605 (6)
N2B—H3B	0.8800	S1F—C2F	1.773 (6)
N2B—H2B	0.8800	S1F—C1F	1.794 (6)
N3B—C4B	1.336 (4)	C1F—H1F	0.9800
C4B—N4B	1.328 (4)	C1F—H2F	0.9800
C4B—C4AB	1.432 (5)	C1F—H3F	0.9800
N4B—H4B	0.8800	C2F—H4F	0.9800
N4B—H5B	0.8800	C2F—H5F	0.9800
C4AB—N5B	1.358 (4)	C2F—H6F	0.9800
C4AB—C8AB	1.391 (5)	S1F'—O1F'	1.507 (11)
N5B—C6B	1.307 (4)	S1F'—C2F'	1.800 (11)
C6B—C7B	1.456 (5)	S1F'—C1F'	1.821 (12)
C6B—C9B	1.484 (5)	C1F'—H1F'	0.9800
C7B—N7B	1.330 (4)	C1F'—H2F'	0.9800
C7B—N8B	1.339 (4)	C1F'—H3F'	0.9800
N7B—H6B	0.83 (4)	C2F'—H4F'	0.9800
N7B—H7B	0.86 (5)	C2F'—H5F'	0.9800
N8B—C8AB	1.345 (4)	C2F'—H6F'	0.9800
C9B—C10B	1.376 (5)
C2A—N1A—C8AA	120.0 (3)	C11B—C10B—H10B	119.7
C2A—N1A—H1XA	117 (3)	C12B—C11B—C10B	120.0 (4)
C8AA—N1A—H1XA	122 (3)	C12B—C11B—H11B	120.0
N2A—C2A—N3A	119.0 (3)	C10B—C11B—H11B	120.0
N2A—C2A—N1A	117.6 (3)	C11B—C12B—C13B	119.9 (4)
N3A—C2A—N1A	123.4 (3)	C11B—C12B—H12B	120.0
C2A—N2A—H3A	120.0	C13B—C12B—H12B	120.0
C2A—N2A—H2A	120.0	C12B—C13B—C14B	120.5 (4)
H3A—N2A—H2A	120.0	C12B—C13B—H13B	119.7
C2A—N3A—C4A	118.5 (3)	C14B—C13B—H13B	119.7
N4A—C4A—N3A	119.1 (3)	C13B—C14B—C9B	119.7 (4)
N4A—C4A—C4AA	120.3 (3)	C13B—C14B—H14B	120.1
N3A—C4A—C4AA	120.6 (3)	C9B—C14B—H14B	120.1
N5A—C4AA—C8AA	121.2 (3)	O2C—C1C—O1C	124.3 (3)
N5A—C4AA—C4A	120.2 (3)	O2C—C1C—C2C	118.7 (3)
C8AA—C4AA—C4A	118.6 (3)	O1C—C1C—C2C	117.0 (3)
C4A—N4A—H4A	120.0	C1C—C2C—C3C	115.5 (3)
C4A—N4A—H5A	120.0	C1C—C2C—H1C	108.4
H4A—N4A—H5A	120.0	C3C—C2C—H1C	108.4
C6A—N5A—C4AA	117.6 (3)	C1C—C2C—H2C	108.4
N5A—C6A—C7A	120.4 (3)	C3C—C2C—H2C	108.4
N5A—C6A—C9A	117.3 (3)	H1C—C2C—H2C	107.5
C7A—C6A—C9A	122.4 (3)	C3C^i—C3C—C2C	114.1 (4)
N7A—C7A—N8A	118.3 (3)	C3C^i—C3C—H3C	108.7
N7A—C7A—C6A	120.4 (3)	C2C—C3C—H3C	108.7
N8A—C7A—C6A	121.4 (3)	C3C^i—C3C—H4C	108.7
C7A—N7A—H6A	121 (3)	C2C—C3C—H4C	108.7
C7A—N7A—H7A	117 (3)	H3C—C3C—H4C	107.6
H6A—N7A—H7A	120 (4)	O2D—C1D—O1D	124.7 (3)
C7A—N8A—C8AA	116.1 (3)	O2D—C1D—C2D	118.3 (3)
N8A—C8AA—N1A	118.7 (3)	O1D—C1D—C2D	117.0 (3)
N8A—C8AA—C4AA	122.6 (3)	C1D—C2D—C3D	112.7 (3)
N1A—C8AA—C4AA	118.7 (3)	C1D—C2D—H1D	109.1
C14A—C9A—C10A	119.1 (3)	C3D—C2D—H1D	109.1
C14A—C9A—C6A	119.9 (3)	C1D—C2D—H2D	109.1
C10A—C9A—C6A	120.9 (3)	C3D—C2D—H2D	109.1
C11A—C10A—C9A	120.6 (4)	H1D—C2D—H2D	107.8
C11A—C10A—H10A	119.7	C3D^ii—C3D—C2D	113.8 (4)
C9A—C10A—H10A	119.7	C3D^ii—C3D—H3D	108.8
C10A—C11A—C12A	119.6 (4)	C2D—C3D—H3D	108.8
C10A—C11A—H11A	120.2	C3D^ii—C3D—H4D	108.8
C12A—C11A—H11A	120.2	C2D—C3D—H4D	108.8
C13A—C12A—C11A	120.5 (4)	H3D—C3D—H4D	107.7
C13A—C12A—H12A	119.7	O1E—S1E—C1E	105.73 (19)
C11A—C12A—H12A	119.7	O1E—S1E—C2E	105.9 (2)
C12A—C13A—C14A	119.9 (3)	C1E—S1E—C2E	98.2 (2)
C12A—C13A—H13A	120.0	S1E—C1E—H1E	109.5
C14A—C13A—H13A	120.0	S1E—C1E—H2E	109.5
C9A—C14A—C13A	120.1 (3)	H1E—C1E—H2E	109.5
C9A—C14A—H14A	119.9	S1E—C1E—H3E	109.5
C13A—C14A—H14A	119.9	H1E—C1E—H3E	109.5
C2B—N1B—C8AB	119.5 (3)	H2E—C1E—H3E	109.5
C2B—N1B—H1XB	118 (3)	S1E—C2E—H4E	109.5
C8AB—N1B—H1XB	123 (3)	S1E—C2E—H5E	109.5
N2B—C2B—N3B	118.9 (3)	H4E—C2E—H5E	109.5
N2B—C2B—N1B	117.2 (3)	S1E—C2E—H6E	109.5
N3B—C2B—N1B	123.9 (3)	H4E—C2E—H6E	109.5
C2B—N2B—H3B	120.0	H5E—C2E—H6E	109.5
C2B—N2B—H2B	120.0	O1F—S1F—C2F	103.9 (3)
H3B—N2B—H2B	120.0	O1F—S1F—C1F	101.9 (3)
C4B—N3B—C2B	118.1 (3)	C2F—S1F—C1F	99.0 (3)
N4B—C4B—N3B	118.9 (3)	S1F—C1F—H1F	109.5
N4B—C4B—C4AB	119.8 (3)	S1F—C1F—H2F	109.5
N3B—C4B—C4AB	121.3 (3)	H1F—C1F—H2F	109.5
C4B—N4B—H4B	120.0	S1F—C1F—H3F	109.5
C4B—N4B—H5B	120.0	H1F—C1F—H3F	109.5
H4B—N4B—H5B	120.0	H2F—C1F—H3F	109.5
N5B—C4AB—C8AB	121.1 (3)	S1F—C2F—H4F	109.5
N5B—C4AB—C4B	120.2 (3)	S1F—C2F—H5F	109.5
C8AB—C4AB—C4B	118.7 (3)	H4F—C2F—H5F	109.5
C6B—N5B—C4AB	118.2 (3)	S1F—C2F—H6F	109.5
N5B—C6B—C7B	120.4 (3)	H4F—C2F—H6F	109.5
N5B—C6B—C9B	116.8 (3)	H5F—C2F—H6F	109.5
C7B—C6B—C9B	122.8 (3)	O1F'—S1F'—C2F'	96.2 (7)
N7B—C7B—N8B	118.8 (3)	O1F'—S1F'—C1F'	98.6 (8)
N7B—C7B—C6B	120.0 (3)	C2F'—S1F'—C1F'	96.6 (7)
N8B—C7B—C6B	121.2 (3)	S1F'—C1F'—H1F'	109.5
C7B—N7B—H6B	119 (3)	S1F'—C1F'—H2F'	109.5
C7B—N7B—H7B	120 (3)	H1F'—C1F'—H2F'	109.5
H6B—N7B—H7B	120 (4)	S1F'—C1F'—H3F'	109.5
C7B—N8B—C8AB	116.5 (3)	H1F'—C1F'—H3F'	109.5
N8B—C8AB—N1B	119.0 (3)	H2F'—C1F'—H3F'	109.5
N8B—C8AB—C4AB	122.4 (3)	S1F'—C2F'—H4F'	109.5
N1B—C8AB—C4AB	118.5 (3)	S1F'—C2F'—H5F'	109.5
C10B—C9B—C14B	119.1 (3)	H4F'—C2F'—H5F'	109.5
C10B—C9B—C6B	120.3 (3)	S1F'—C2F'—H6F'	109.5
C14B—C9B—C6B	120.3 (3)	H4F'—C2F'—H6F'	109.5
C9B—C10B—C11B	120.6 (4)	H5F'—C2F'—H6F'	109.5
C9B—C10B—H10B	119.7
C8AA—N1A—C2A—N2A	179.7 (3)	N1B—C2B—N3B—C4B	−0.6 (5)
C8AA—N1A—C2A—N3A	−2.0 (5)	C2B—N3B—C4B—N4B	−177.5 (3)
N2A—C2A—N3A—C4A	179.5 (3)	C2B—N3B—C4B—C4AB	0.9 (5)
N1A—C2A—N3A—C4A	1.3 (5)	N4B—C4B—C4AB—N5B	−1.7 (5)
C2A—N3A—C4A—N4A	−177.5 (3)	N3B—C4B—C4AB—N5B	−180.0 (3)
C2A—N3A—C4A—C4AA	2.4 (5)	N4B—C4B—C4AB—C8AB	176.6 (3)
N4A—C4A—C4AA—N5A	−7.7 (5)	N3B—C4B—C4AB—C8AB	−1.7 (5)
N3A—C4A—C4AA—N5A	172.3 (3)	C8AB—C4AB—N5B—C6B	−0.6 (5)
N4A—C4A—C4AA—C8AA	174.6 (3)	C4B—C4AB—N5B—C6B	177.6 (3)
N3A—C4A—C4AA—C8AA	−5.4 (5)	C4AB—N5B—C6B—C7B	−2.7 (5)
C8AA—C4AA—N5A—C6A	−2.0 (5)	C4AB—N5B—C6B—C9B	178.0 (3)
C4A—C4AA—N5A—C6A	−179.6 (3)	N5B—C6B—C7B—N7B	−175.1 (3)
C4AA—N5A—C6A—C7A	−5.7 (5)	C9B—C6B—C7B—N7B	4.2 (5)
C4AA—N5A—C6A—C9A	173.5 (3)	N5B—C6B—C7B—N8B	4.3 (5)
N5A—C6A—C7A—N7A	−170.9 (3)	C9B—C6B—C7B—N8B	−176.4 (3)
C9A—C6A—C7A—N7A	10.0 (5)	N7B—C7B—N8B—C8AB	177.2 (3)
N5A—C6A—C7A—N8A	9.1 (5)	C6B—C7B—N8B—C8AB	−2.3 (5)
C9A—C6A—C7A—N8A	−170.1 (3)	C7B—N8B—C8AB—N1B	−178.8 (3)
N7A—C7A—N8A—C8AA	176.1 (3)	C7B—N8B—C8AB—C4AB	−1.1 (5)
C6A—C7A—N8A—C8AA	−3.8 (5)	C2B—N1B—C8AB—N8B	175.9 (3)
C7A—N8A—C8AA—N1A	176.4 (3)	C2B—N1B—C8AB—C4AB	−1.9 (5)
C7A—N8A—C8AA—C4AA	−4.0 (5)	N5B—C4AB—C8AB—N8B	2.7 (5)
C2A—N1A—C8AA—N8A	178.5 (3)	C4B—C4AB—C8AB—N8B	−175.6 (3)
C2A—N1A—C8AA—C4AA	−1.1 (5)	N5B—C4AB—C8AB—N1B	−179.6 (3)
N5A—C4AA—C8AA—N8A	7.4 (5)	C4B—C4AB—C8AB—N1B	2.1 (5)
C4A—C4AA—C8AA—N8A	−175.0 (3)	N5B—C6B—C9B—C10B	91.3 (4)
N5A—C4AA—C8AA—N1A	−173.1 (3)	C7B—C6B—C9B—C10B	−88.0 (4)
C4A—C4AA—C8AA—N1A	4.6 (5)	N5B—C6B—C9B—C14B	−83.3 (4)
N5A—C6A—C9A—C14A	−113.9 (4)	C7B—C6B—C9B—C14B	97.4 (4)
C7A—C6A—C9A—C14A	65.3 (4)	C14B—C9B—C10B—C11B	1.7 (6)
N5A—C6A—C9A—C10A	61.2 (4)	C6B—C9B—C10B—C11B	−173.0 (3)
C7A—C6A—C9A—C10A	−119.6 (4)	C9B—C10B—C11B—C12B	−0.3 (6)
C14A—C9A—C10A—C11A	0.0 (5)	C10B—C11B—C12B—C13B	−1.6 (6)
C6A—C9A—C10A—C11A	−175.1 (3)	C11B—C12B—C13B—C14B	2.1 (6)
C9A—C10A—C11A—C12A	1.6 (6)	C12B—C13B—C14B—C9B	−0.8 (6)
C10A—C11A—C12A—C13A	−1.6 (6)	C10B—C9B—C14B—C13B	−1.1 (5)
C11A—C12A—C13A—C14A	−0.1 (5)	C6B—C9B—C14B—C13B	173.5 (3)
C10A—C9A—C14A—C13A	−1.7 (5)	O2C—C1C—C2C—C3C	37.8 (5)
C6A—C9A—C14A—C13A	173.5 (3)	O1C—C1C—C2C—C3C	−144.7 (3)
C12A—C13A—C14A—C9A	1.7 (5)	C1C—C2C—C3C—C3C^i	66.6 (5)
C8AB—N1B—C2B—N2B	−177.7 (3)	O2D—C1D—C2D—C3D	−58.8 (4)
C8AB—N1B—C2B—N3B	1.1 (5)	O1D—C1D—C2D—C3D	121.4 (3)
N2B—C2B—N3B—C4B	178.2 (3)	C1D—C2D—C3D—C3D^ii	−58.9 (5)

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

Triamterenium pimelate, DMSO solvate (1d_DMSO)

Crystal data

2(C12H12N7^+)·C7H10O4^2^−·2(C2H6OS)	Z = 4
Mr = 822.98	F(000) = 1736
Triclinic, P1	Dx = 1.402 Mg m^−3
a = 14.0750 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 14.8889 (6) Å	Cell parameters from 59468 reflections
c = 19.635 (2) Å	θ = 1.0–25.4°
α = 86.408 (2)°	µ = 0.20 mm^−1
β = 88.142 (3)°	T = 150 K
γ = 71.702 (2)°	Block, colourless
V = 3898.7 (5) Å^3	0.14 × 0.07 × 0.05 mm

Data collection

Nonius Kappa CCD diffractometer	13988 independent reflections
Radiation source: fine-focus sealed tube	5187 reflections with I > 2σ(I)
None monochromator	Rint = 0.114
Thin slice ω and φ scans	θmax = 25.4°, θmin = 3.5°
Absorption correction: multi-scan multi-scan from symmetry-related measurements Sortav (Blessing 1995)	h = −16→16
Tmin = 0.932, Tmax = 1.000	k = −17→17
32837 measured reflections	l = −19→23

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.079	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.220	H-atom parameters constrained
S = 0.95	w = 1/[σ^2(Fo^2) + (0.0923P)^2] where P = (Fo^2 + 2Fc^2)/3
13988 reflections	(Δ/σ)max < 0.001
1035 parameters	Δρmax = 0.78 e Å^−3
0 restraints	Δρmin = −0.38 e Å^−3

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
N1A	−0.3412 (4)	0.8401 (3)	0.5162 (3)	0.0348 (14)
H1XA	−0.3116	0.8827	0.5037	0.042*
C2A	−0.3044 (5)	0.7509 (4)	0.4949 (4)	0.0357 (17)
N2A	−0.2276 (4)	0.7330 (3)	0.4508 (3)	0.0466 (16)
H3A	−0.2017	0.6758	0.4359	0.056*
H2A	−0.2028	0.7784	0.4367	0.056*
N3A	−0.3411 (4)	0.6802 (3)	0.5158 (3)	0.0367 (14)
C4A	−0.4226 (5)	0.7003 (4)	0.5571 (3)	0.0310 (16)
N4A	−0.4587 (4)	0.6328 (3)	0.5781 (3)	0.0397 (15)
H4A	−0.4300	0.5748	0.5654	0.048*
H5A	−0.5119	0.6453	0.6051	0.048*
C4AA	−0.4688 (5)	0.7966 (4)	0.5772 (3)	0.0264 (15)
N5A	−0.5508 (4)	0.8155 (3)	0.6190 (3)	0.0336 (14)
C6A	−0.5879 (4)	0.9026 (4)	0.6389 (3)	0.0275 (15)
C7A	−0.5412 (5)	0.9732 (4)	0.6181 (3)	0.0354 (17)
N7A	−0.5770 (4)	1.0625 (3)	0.6373 (3)	0.0369 (14)
H7A	−0.5474	1.1044	0.6229	0.044*
H6A	−0.6302	1.0794	0.6641	0.044*
N8A	−0.4592 (4)	0.9544 (3)	0.5768 (3)	0.0314 (13)
C8AA	−0.4245 (5)	0.8638 (4)	0.5574 (3)	0.0297 (16)
C9A	−0.6754 (5)	0.9193 (4)	0.6869 (3)	0.0328 (16)
C10A	−0.6843 (5)	0.9702 (5)	0.7456 (4)	0.0458 (19)
H10A	−0.6350	0.9988	0.7553	0.055*
C11A	−0.7652 (5)	0.9788 (5)	0.7895 (4)	0.0462 (19)
H11A	−0.7707	1.0126	0.8297	0.055*
C12A	−0.8379 (5)	0.9388 (5)	0.7754 (4)	0.0441 (19)
H12A	−0.8939	0.9459	0.8053	0.053*
C13A	−0.8287 (5)	0.8893 (4)	0.7187 (4)	0.046 (2)
H13A	−0.8789	0.8618	0.7091	0.055*
C14A	−0.7481 (5)	0.8781 (4)	0.6745 (4)	0.0394 (18)
H14A	−0.7425	0.8420	0.6355	0.047*
N1B	−0.4818 (4)	0.3749 (3)	0.5968 (3)	0.0306 (13)
H1XB	−0.5117	0.4326	0.6098	0.037*
C2B	−0.5172 (5)	0.3033 (4)	0.6201 (4)	0.0358 (17)
N2B	−0.5934 (4)	0.3226 (3)	0.6615 (3)	0.0412 (15)
H3B	−0.6186	0.2777	0.6763	0.049*
H2B	−0.6201	0.3806	0.6749	0.049*
N3B	−0.4776 (4)	0.2141 (3)	0.6003 (3)	0.0325 (14)
C4B	−0.3954 (5)	0.1948 (4)	0.5588 (3)	0.0324 (16)
N4B	−0.3550 (4)	0.1049 (3)	0.5415 (3)	0.0388 (15)
H4B	−0.3817	0.0614	0.5570	0.047*
H5B	−0.3017	0.0893	0.5147	0.047*
C4AB	−0.3543 (5)	0.2669 (4)	0.5339 (3)	0.0302 (16)
N5B	−0.2743 (4)	0.2478 (3)	0.4906 (3)	0.0337 (14)
C6B	−0.2421 (5)	0.3175 (4)	0.4661 (3)	0.0321 (17)
C7B	−0.2912 (5)	0.4134 (4)	0.4898 (4)	0.0355 (17)
N7B	−0.2563 (4)	0.4843 (3)	0.4689 (3)	0.0426 (15)
H7B	−0.2850	0.5415	0.4833	0.051*
H6B	−0.2045	0.4739	0.4407	0.051*
N8B	−0.3685 (4)	0.4317 (3)	0.5318 (3)	0.0339 (14)
C8AB	−0.4011 (5)	0.3592 (4)	0.5537 (3)	0.0330 (17)
C9B	−0.1543 (5)	0.2960 (4)	0.4203 (4)	0.0338 (17)
C10B	−0.1504 (5)	0.3476 (4)	0.3590 (4)	0.0399 (18)
H10B	−0.2052	0.4018	0.3466	0.048*
C11B	−0.0680 (6)	0.3207 (5)	0.3164 (4)	0.048 (2)
H11B	−0.0671	0.3549	0.2740	0.058*
C12B	0.0146 (5)	0.2428 (5)	0.3356 (4)	0.047 (2)
H12B	0.0721	0.2253	0.3067	0.057*
C13B	0.0126 (5)	0.1917 (5)	0.3964 (4)	0.050 (2)
H13B	0.0684	0.1391	0.4100	0.060*
C14B	−0.0719 (5)	0.2186 (4)	0.4367 (4)	0.0455 (19)
H14B	−0.0739	0.1822	0.4779	0.055*
N1C	−0.1600 (4)	−0.3410 (3)	1.0223 (3)	0.0340 (14)
H1XC	−0.1897	−0.3813	1.0101	0.041*
C2C	−0.1966 (5)	−0.2463 (4)	1.0008 (4)	0.0341 (17)
N3C	−0.1615 (4)	−0.1796 (3)	1.0245 (3)	0.0308 (13)
C4C	−0.0824 (5)	−0.2078 (4)	1.0657 (3)	0.0288 (16)
C4AC	−0.0387 (4)	−0.3056 (4)	1.0856 (3)	0.0257 (15)
N5C	0.0442 (4)	−0.3334 (3)	1.1269 (3)	0.0310 (13)
N8C	−0.0421 (4)	−0.4642 (3)	1.0801 (3)	0.0329 (14)
N2C	−0.2714 (4)	−0.2207 (3)	0.9584 (3)	0.0390 (15)
H3C	−0.2983	−0.1605	0.9456	0.047*
H2C	−0.2948	−0.2636	0.9428	0.047*
N4C	−0.0470 (3)	−0.1418 (3)	1.0879 (3)	0.0333 (14)
H4C	−0.0756	−0.0818	1.0754	0.040*
H5C	0.0049	−0.1583	1.1150	0.040*
C6C	0.0848 (5)	−0.4239 (4)	1.1436 (4)	0.0340 (17)
C7C	0.0415 (5)	−0.4916 (4)	1.1194 (3)	0.0325 (17)
N7C	0.0809 (4)	−0.5850 (3)	1.1341 (3)	0.0397 (15)
H7C	0.0529	−0.6247	1.1186	0.048*
H6C	0.1349	−0.6066	1.1592	0.048*
C8AC	−0.0775 (5)	−0.3716 (4)	1.0627 (3)	0.0282 (16)
C9C	0.1727 (4)	−0.4482 (4)	1.1883 (3)	0.0294 (16)
C10C	0.1915 (5)	−0.5145 (4)	1.2426 (3)	0.0337 (17)
H10C	0.1469	−0.5505	1.2513	0.040*
C11C	0.2719 (5)	−0.5305 (4)	1.2848 (4)	0.047 (2)
H11C	0.2832	−0.5779	1.3210	0.056*
C12C	0.3358 (5)	−0.4775 (4)	1.2741 (4)	0.0428 (19)
H12C	0.3909	−0.4873	1.3035	0.051*
C13C	0.3197 (5)	−0.4098 (5)	1.2205 (4)	0.0433 (19)
H13C	0.3643	−0.3735	1.2131	0.052*
C14C	0.2398 (5)	−0.3944 (4)	1.1777 (4)	0.0398 (18)
H14C	0.2295	−0.3478	1.1411	0.048*
N1D	−0.0121 (4)	1.1122 (3)	0.0888 (3)	0.0339 (14)
H1XD	0.0193	1.0527	0.1010	0.041*
C2D	0.0204 (5)	1.1828 (4)	0.1105 (3)	0.0316 (16)
N3D	−0.0186 (4)	1.2739 (3)	0.0912 (3)	0.0322 (13)
C4D	−0.1013 (5)	1.2998 (4)	0.0524 (4)	0.0336 (17)
C4AD	−0.1423 (5)	1.2300 (4)	0.0287 (3)	0.0316 (17)
N5D	−0.2240 (4)	1.2551 (3)	−0.0111 (3)	0.0304 (13)
N8D	−0.1265 (4)	1.0640 (3)	0.0302 (3)	0.0314 (13)
N2D	0.0988 (4)	1.1575 (3)	0.1512 (3)	0.0435 (16)
H3D	0.1238	1.2006	0.1648	0.052*
H2D	0.1259	1.0976	0.1648	0.052*
N4D	−0.1433 (4)	1.3907 (3)	0.0353 (3)	0.0383 (15)
H4D	−0.1173	1.4329	0.0492	0.046*
H5D	−0.1972	1.4090	0.0100	0.046*
C6D	−0.2568 (5)	1.1878 (4)	−0.0329 (3)	0.0325 (17)
C7D	−0.2067 (5)	1.0895 (4)	−0.0110 (3)	0.0309 (16)
N7D	−0.2411 (4)	1.0201 (3)	−0.0289 (3)	0.0403 (15)
H7D	−0.2116	0.9613	−0.0138	0.048*
H6D	−0.2932	1.0334	−0.0557	0.048*
C8AD	−0.0938 (5)	1.1349 (4)	0.0479 (3)	0.0289 (16)
C9D	−0.3464 (4)	1.2154 (4)	−0.0752 (3)	0.0294 (16)
C10D	−0.3522 (5)	1.1746 (4)	−0.1362 (4)	0.0382 (18)
H10D	−0.2974	1.1232	−0.1506	0.046*
C11D	−0.4368 (5)	1.2077 (5)	−0.1761 (4)	0.046 (2)
H11D	−0.4385	1.1805	−0.2183	0.056*
C12D	−0.5191 (5)	1.2802 (4)	−0.1547 (4)	0.048 (2)
H12D	−0.5771	1.3031	−0.1821	0.058*
C13D	−0.5157 (5)	1.3191 (4)	−0.0926 (4)	0.0425 (19)
H13D	−0.5727	1.3665	−0.0762	0.051*
C14D	−0.4299 (5)	1.2887 (4)	−0.0553 (4)	0.0425 (19)
H14D	−0.4272	1.3187	−0.0144	0.051*
C1E	−0.1644 (5)	0.9261 (5)	0.4352 (4)	0.0391 (18)
O1E	−0.2218 (3)	0.9506 (3)	0.4850 (3)	0.0446 (13)
C2E	−0.0719 (5)	0.9576 (4)	0.4282 (4)	0.0420 (19)
H2E	−0.0417	0.9532	0.4736	0.050*
H3E	−0.0912	1.0247	0.4108	0.050*
O2E	−0.1816 (4)	0.8777 (3)	0.3887 (3)	0.0610 (15)
C3E	0.0071 (6)	0.8951 (5)	0.3784 (4)	0.064 (2)
H4E	0.0239	0.8281	0.3957	0.077*
H5E	−0.0241	0.9004	0.3333	0.077*
O3E	0.0701 (3)	0.9369 (3)	0.1547 (3)	0.0398 (12)
C4E	0.1008 (5)	0.9191 (5)	0.3691 (4)	0.058 (2)
H6E	0.1302	0.9187	0.4143	0.070*
H7E	0.0858	0.9838	0.3475	0.070*
O4E	0.1642 (3)	0.9899 (3)	0.2207 (2)	0.0482 (13)
C5E	0.1772 (5)	0.8490 (5)	0.3245 (4)	0.0471 (19)
H8E	0.1956	0.7855	0.3485	0.056*
H9E	0.2385	0.8682	0.3202	0.056*
C6E	0.1421 (5)	0.8406 (4)	0.2524 (4)	0.0381 (18)
H10E	0.1938	0.7890	0.2302	0.046*
H11E	0.0801	0.8225	0.2565	0.046*
C7E	0.1220 (5)	0.9302 (4)	0.2070 (4)	0.0400 (18)
C1F	−0.3368 (5)	−0.4101 (5)	0.9330 (4)	0.0351 (17)
O1F	−0.2759 (3)	−0.4460 (3)	0.9793 (3)	0.0418 (12)
C2F	−0.4241 (5)	−0.4484 (4)	0.9249 (4)	0.0374 (18)
H2F	−0.3972	−0.5143	0.9106	0.045*
H3F	−0.4572	−0.4503	0.9700	0.045*
O2F	−0.3333 (3)	−0.3420 (3)	0.8923 (2)	0.0465 (13)
C3F	−0.5020 (5)	−0.3923 (4)	0.8742 (4)	0.0411 (18)
H4F	−0.4694	−0.3924	0.8288	0.049*
H5F	−0.5270	−0.3258	0.8875	0.049*
O3F	−0.6513 (3)	−0.5169 (3)	0.7339 (2)	0.0472 (13)
C4F	−0.5922 (4)	−0.4288 (4)	0.8680 (4)	0.0373 (18)
H6F	−0.5684	−0.4936	0.8514	0.045*
H7F	−0.6229	−0.4323	0.9137	0.045*
O4F	−0.5715 (3)	−0.4564 (3)	0.6518 (3)	0.0422 (12)
C5F	−0.6714 (5)	−0.3661 (4)	0.8196 (4)	0.046 (2)
H8F	−0.6933	−0.3009	0.8357	0.056*
H9F	−0.7303	−0.3891	0.8222	0.056*
C6F	−0.6378 (5)	−0.3622 (4)	0.7449 (3)	0.0364 (17)
H10F	−0.6897	−0.3112	0.7199	0.044*
H11F	−0.5757	−0.3442	0.7429	0.044*
C7F	−0.6184 (5)	−0.4527 (5)	0.7079 (4)	0.0405 (18)
C1G	0.0578 (6)	0.6091 (5)	0.3990 (4)	0.065 (2)
H1G	0.0203	0.6720	0.3794	0.097*
H2G	0.1275	0.5923	0.3829	0.097*
H3G	0.0557	0.6100	0.4489	0.097*
O1G	−0.0955 (3)	0.5463 (3)	0.4094 (2)	0.0459 (13)
S1G	0.00322 (13)	0.52427 (12)	0.37339 (10)	0.0442 (5)
C2G	0.0826 (5)	0.4230 (4)	0.4187 (4)	0.056 (2)
H4G	0.0780	0.4336	0.4676	0.085*
H5G	0.1518	0.4117	0.4027	0.085*
H6G	0.0617	0.3676	0.4107	0.085*
C1H	−0.5350 (5)	−0.1169 (5)	−0.0853 (4)	0.058 (2)
H4H	−0.4861	−0.1783	−0.0947	0.086*
H5H	−0.5993	−0.1123	−0.1055	0.086*
H6H	−0.5437	−0.1114	−0.0358	0.086*
O1H	−0.4029 (3)	−0.0265 (3)	−0.0795 (2)	0.0442 (13)
S1H	−0.49107 (13)	−0.02327 (11)	−0.12155 (10)	0.0412 (5)
C2H	−0.5922 (5)	0.0725 (4)	−0.0929 (4)	0.0462 (19)
H1H	−0.6054	0.0608	−0.0444	0.069*
H2H	−0.6520	0.0782	−0.1192	0.069*
H3H	−0.5749	0.1313	−0.0993	0.069*
C1I	0.3932 (5)	0.2297 (5)	0.2514 (4)	0.062 (2)
H1I	0.3929	0.2876	0.2247	0.092*
H2I	0.4602	0.1832	0.2495	0.092*
H3I	0.3750	0.2444	0.2989	0.092*
O1I	0.2039 (3)	0.2564 (3)	0.2261 (2)	0.0424 (12)
S1I	0.30583 (14)	0.18230 (12)	0.21719 (11)	0.0510 (6)
C2I	0.3110 (6)	0.0922 (5)	0.2821 (4)	0.068 (2)
H4I	0.2878	0.1213	0.3255	0.101*
H5I	0.3800	0.0503	0.2866	0.101*
H6I	0.2678	0.0554	0.2699	0.101*
C1J	0.8105 (5)	0.6263 (4)	0.2340 (4)	0.058 (2)
H1J	0.8104	0.6129	0.2835	0.087*
H2J	0.8771	0.5946	0.2152	0.087*
H3J	0.7611	0.6029	0.2133	0.087*
O1J	0.6869 (3)	0.7982 (3)	0.2582 (2)	0.0478 (13)
S1J	0.77936 (14)	0.75168 (12)	0.21593 (11)	0.0504 (6)
C2J	0.8801 (5)	0.7683 (5)	0.2584 (4)	0.060 (2)
H4J	0.8734	0.8359	0.2564	0.091*
H5J	0.9431	0.7333	0.2362	0.091*
H6J	0.8798	0.7448	0.3061	0.091*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.032 (3)	0.027 (3)	0.047 (4)	−0.012 (3)	0.003 (3)	−0.001 (3)
C2A	0.032 (4)	0.034 (4)	0.040 (5)	−0.006 (3)	0.005 (4)	−0.013 (3)
N2A	0.036 (4)	0.026 (3)	0.077 (5)	−0.008 (3)	0.009 (4)	−0.010 (3)
N3A	0.036 (3)	0.023 (3)	0.052 (4)	−0.010 (3)	0.002 (3)	−0.006 (3)
C4A	0.027 (4)	0.031 (4)	0.034 (5)	−0.008 (3)	0.001 (4)	−0.004 (3)
N4A	0.040 (3)	0.020 (3)	0.061 (4)	−0.012 (3)	0.008 (3)	−0.004 (3)
C4AA	0.033 (4)	0.018 (3)	0.028 (4)	−0.009 (3)	0.005 (3)	−0.003 (3)
N5A	0.033 (3)	0.028 (3)	0.039 (4)	−0.009 (3)	−0.001 (3)	−0.002 (3)
C6A	0.029 (4)	0.024 (3)	0.030 (4)	−0.008 (3)	0.001 (3)	0.002 (3)
C7A	0.043 (5)	0.030 (4)	0.033 (5)	−0.012 (3)	−0.002 (4)	−0.001 (3)
N7A	0.042 (3)	0.016 (3)	0.051 (4)	−0.008 (3)	0.015 (3)	−0.007 (3)
N8A	0.040 (4)	0.014 (3)	0.036 (4)	−0.003 (2)	0.003 (3)	−0.005 (2)
C8AA	0.023 (4)	0.038 (4)	0.025 (4)	−0.005 (3)	0.004 (3)	−0.002 (3)
C9A	0.029 (4)	0.028 (3)	0.035 (5)	0.000 (3)	0.001 (3)	−0.005 (3)
C10A	0.040 (5)	0.052 (4)	0.051 (6)	−0.022 (4)	0.001 (4)	0.002 (4)
C11A	0.044 (5)	0.052 (4)	0.038 (5)	−0.007 (4)	0.009 (4)	−0.010 (4)
C12A	0.045 (5)	0.044 (4)	0.044 (5)	−0.017 (4)	0.009 (4)	0.001 (4)
C13A	0.039 (5)	0.030 (4)	0.063 (6)	−0.006 (3)	0.001 (4)	0.008 (4)
C14A	0.027 (4)	0.042 (4)	0.051 (5)	−0.013 (3)	0.006 (4)	−0.002 (3)
N1B	0.030 (3)	0.013 (3)	0.045 (4)	−0.001 (2)	0.005 (3)	−0.004 (2)
C2B	0.035 (4)	0.041 (4)	0.039 (5)	−0.021 (4)	−0.001 (4)	−0.006 (3)
N2B	0.041 (4)	0.025 (3)	0.057 (4)	−0.009 (3)	0.010 (3)	−0.008 (3)
N3B	0.034 (3)	0.019 (3)	0.045 (4)	−0.009 (2)	0.007 (3)	−0.007 (3)
C4B	0.028 (4)	0.038 (4)	0.032 (5)	−0.011 (3)	−0.010 (4)	0.003 (3)
N4B	0.039 (3)	0.023 (3)	0.057 (4)	−0.013 (3)	0.007 (3)	−0.009 (3)
C4AB	0.037 (4)	0.021 (3)	0.033 (5)	−0.011 (3)	0.003 (4)	−0.002 (3)
N5B	0.026 (3)	0.028 (3)	0.047 (4)	−0.008 (2)	0.002 (3)	−0.005 (3)
C6B	0.035 (4)	0.025 (4)	0.035 (5)	−0.008 (3)	−0.009 (4)	0.000 (3)
C7B	0.037 (4)	0.024 (4)	0.047 (5)	−0.011 (3)	−0.002 (4)	−0.001 (3)
N7B	0.041 (4)	0.037 (3)	0.057 (4)	−0.022 (3)	0.015 (3)	−0.013 (3)
N8B	0.028 (3)	0.025 (3)	0.050 (4)	−0.011 (2)	0.006 (3)	−0.007 (3)
C8AB	0.033 (4)	0.024 (4)	0.041 (5)	−0.008 (3)	0.003 (4)	−0.001 (3)
C9B	0.034 (4)	0.027 (4)	0.042 (5)	−0.013 (3)	0.004 (4)	−0.005 (3)
C10B	0.039 (5)	0.029 (4)	0.052 (6)	−0.012 (3)	0.012 (4)	−0.007 (4)
C11B	0.060 (6)	0.062 (5)	0.032 (5)	−0.033 (5)	0.003 (4)	−0.005 (4)
C12B	0.043 (5)	0.044 (4)	0.058 (6)	−0.014 (4)	0.009 (4)	−0.018 (4)
C13B	0.039 (5)	0.044 (4)	0.069 (7)	−0.014 (4)	0.015 (5)	−0.008 (4)
C14B	0.044 (5)	0.035 (4)	0.058 (6)	−0.013 (4)	0.009 (4)	−0.001 (4)
N1C	0.040 (4)	0.025 (3)	0.039 (4)	−0.012 (3)	0.003 (3)	−0.004 (3)
C2C	0.031 (4)	0.031 (4)	0.035 (5)	−0.002 (3)	0.003 (4)	−0.002 (3)
N3C	0.036 (3)	0.023 (3)	0.036 (4)	−0.013 (3)	−0.001 (3)	−0.005 (2)
C4C	0.028 (4)	0.032 (4)	0.026 (4)	−0.008 (3)	−0.003 (3)	−0.004 (3)
C4AC	0.022 (4)	0.021 (3)	0.034 (4)	−0.006 (3)	−0.002 (3)	0.001 (3)
N5C	0.035 (3)	0.024 (3)	0.034 (4)	−0.010 (3)	0.007 (3)	−0.006 (2)
N8C	0.033 (3)	0.023 (3)	0.042 (4)	−0.009 (3)	0.000 (3)	−0.004 (3)
N2C	0.036 (3)	0.033 (3)	0.048 (4)	−0.012 (3)	−0.012 (3)	0.001 (3)
N4C	0.030 (3)	0.017 (3)	0.052 (4)	−0.006 (2)	−0.011 (3)	0.002 (2)
C6C	0.026 (4)	0.026 (4)	0.051 (5)	−0.011 (3)	0.006 (4)	0.001 (3)
C7C	0.027 (4)	0.023 (4)	0.044 (5)	−0.004 (3)	0.002 (4)	−0.002 (3)
N7C	0.039 (3)	0.028 (3)	0.053 (4)	−0.010 (3)	−0.016 (3)	0.001 (3)
C8AC	0.029 (4)	0.020 (3)	0.033 (5)	−0.005 (3)	−0.001 (3)	0.002 (3)
C9C	0.024 (4)	0.024 (3)	0.038 (5)	−0.002 (3)	0.000 (3)	−0.007 (3)
C10C	0.033 (4)	0.035 (4)	0.036 (5)	−0.013 (3)	−0.003 (4)	−0.001 (3)
C11C	0.044 (5)	0.039 (4)	0.051 (6)	−0.001 (4)	−0.003 (4)	−0.013 (4)
C12C	0.034 (4)	0.045 (4)	0.052 (6)	−0.015 (4)	−0.015 (4)	0.002 (4)
C13C	0.037 (5)	0.047 (4)	0.046 (5)	−0.013 (4)	0.003 (4)	−0.005 (4)
C14C	0.028 (4)	0.030 (4)	0.060 (6)	−0.007 (3)	0.000 (4)	0.000 (3)
N1D	0.033 (3)	0.019 (3)	0.049 (4)	−0.005 (2)	−0.009 (3)	−0.004 (3)
C2D	0.023 (4)	0.035 (4)	0.036 (5)	−0.008 (3)	0.001 (4)	−0.001 (3)
N3D	0.032 (3)	0.021 (3)	0.044 (4)	−0.009 (3)	0.000 (3)	−0.002 (3)
C4D	0.036 (4)	0.016 (3)	0.048 (5)	−0.008 (3)	0.003 (4)	0.000 (3)
C4AD	0.031 (4)	0.021 (3)	0.046 (5)	−0.013 (3)	−0.001 (4)	−0.001 (3)
N5D	0.028 (3)	0.023 (3)	0.040 (4)	−0.009 (2)	0.002 (3)	0.001 (2)
N8D	0.023 (3)	0.024 (3)	0.045 (4)	−0.003 (2)	0.003 (3)	−0.004 (3)
N2D	0.033 (4)	0.028 (3)	0.069 (5)	−0.008 (3)	−0.005 (3)	−0.004 (3)
N4D	0.032 (3)	0.028 (3)	0.058 (4)	−0.014 (3)	−0.002 (3)	−0.004 (3)
C6D	0.033 (4)	0.023 (3)	0.043 (5)	−0.011 (3)	0.005 (4)	−0.002 (3)
C7D	0.031 (4)	0.018 (3)	0.042 (5)	−0.006 (3)	0.002 (4)	−0.002 (3)
N7D	0.039 (3)	0.031 (3)	0.053 (4)	−0.015 (3)	−0.003 (3)	0.001 (3)
C8AD	0.032 (4)	0.018 (3)	0.036 (5)	−0.007 (3)	−0.002 (4)	−0.003 (3)
C9D	0.027 (4)	0.026 (3)	0.037 (5)	−0.010 (3)	−0.001 (3)	−0.004 (3)
C10D	0.025 (4)	0.024 (3)	0.064 (6)	−0.007 (3)	0.003 (4)	−0.005 (4)
C11D	0.048 (5)	0.043 (4)	0.055 (6)	−0.023 (4)	−0.005 (4)	−0.003 (4)
C12D	0.041 (5)	0.034 (4)	0.069 (6)	−0.012 (4)	−0.014 (4)	0.005 (4)
C13D	0.024 (4)	0.039 (4)	0.061 (6)	−0.005 (3)	−0.003 (4)	−0.002 (4)
C14D	0.045 (5)	0.028 (4)	0.053 (5)	−0.009 (4)	0.004 (4)	0.000 (3)
C1E	0.043 (5)	0.033 (4)	0.042 (5)	−0.015 (4)	0.007 (4)	0.002 (4)
O1E	0.040 (3)	0.036 (3)	0.058 (4)	−0.012 (2)	0.015 (3)	−0.012 (2)
C2E	0.033 (4)	0.039 (4)	0.054 (5)	−0.010 (3)	0.003 (4)	−0.004 (4)
O2E	0.078 (4)	0.054 (3)	0.060 (4)	−0.034 (3)	0.024 (3)	−0.020 (3)
C3E	0.057 (5)	0.057 (5)	0.083 (7)	−0.026 (4)	0.016 (5)	−0.016 (5)
O3E	0.039 (3)	0.030 (2)	0.051 (4)	−0.011 (2)	−0.010 (3)	−0.001 (2)
C4E	0.045 (5)	0.071 (5)	0.059 (6)	−0.018 (4)	0.001 (4)	−0.003 (4)
O4E	0.054 (3)	0.033 (3)	0.063 (4)	−0.019 (2)	−0.018 (3)	0.002 (2)
C5E	0.036 (4)	0.054 (4)	0.040 (5)	0.001 (4)	−0.002 (4)	0.003 (4)
C6E	0.032 (4)	0.027 (4)	0.052 (6)	−0.006 (3)	0.012 (4)	−0.001 (3)
C7E	0.030 (4)	0.035 (4)	0.048 (6)	−0.002 (3)	0.004 (4)	0.002 (4)
C1F	0.028 (4)	0.032 (4)	0.042 (5)	−0.004 (3)	0.002 (4)	−0.004 (4)
O1F	0.034 (3)	0.030 (2)	0.063 (4)	−0.011 (2)	−0.011 (3)	−0.001 (2)
C2F	0.034 (4)	0.027 (3)	0.051 (5)	−0.008 (3)	0.004 (4)	−0.006 (3)
O2F	0.056 (3)	0.040 (3)	0.051 (4)	−0.027 (2)	−0.011 (3)	0.007 (2)
C3F	0.038 (4)	0.041 (4)	0.047 (5)	−0.016 (3)	−0.002 (4)	−0.006 (4)
O3F	0.054 (3)	0.035 (3)	0.056 (4)	−0.021 (2)	0.012 (3)	−0.004 (2)
C4F	0.032 (4)	0.036 (4)	0.047 (5)	−0.017 (3)	0.004 (4)	−0.002 (3)
O4F	0.048 (3)	0.039 (3)	0.045 (4)	−0.021 (2)	0.013 (3)	−0.008 (2)
C5F	0.030 (4)	0.047 (4)	0.062 (6)	−0.009 (3)	−0.006 (4)	−0.011 (4)
C6F	0.037 (4)	0.035 (4)	0.037 (5)	−0.010 (3)	−0.001 (4)	−0.002 (3)
C7F	0.029 (4)	0.040 (4)	0.046 (6)	−0.001 (3)	−0.003 (4)	−0.004 (4)
C1G	0.056 (5)	0.064 (5)	0.085 (7)	−0.034 (4)	0.013 (5)	−0.012 (5)
O1G	0.032 (3)	0.039 (3)	0.069 (4)	−0.013 (2)	0.012 (3)	−0.014 (2)
S1G	0.0386 (12)	0.0427 (10)	0.0491 (14)	−0.0097 (9)	0.0037 (10)	−0.0056 (9)
C2G	0.053 (5)	0.050 (4)	0.061 (6)	−0.007 (4)	−0.003 (4)	−0.011 (4)
C1H	0.045 (5)	0.053 (4)	0.083 (7)	−0.025 (4)	−0.006 (4)	−0.004 (4)
O1H	0.027 (3)	0.036 (2)	0.067 (4)	−0.007 (2)	−0.011 (3)	0.005 (2)
S1H	0.0378 (11)	0.0345 (9)	0.0498 (14)	−0.0092 (8)	−0.0018 (10)	−0.0020 (8)
C2H	0.033 (4)	0.033 (4)	0.064 (6)	0.002 (3)	0.004 (4)	−0.008 (4)
C1I	0.045 (5)	0.076 (5)	0.071 (7)	−0.031 (4)	−0.005 (4)	0.007 (5)
O1I	0.028 (3)	0.035 (2)	0.058 (4)	−0.001 (2)	−0.002 (2)	−0.003 (2)
S1I	0.0438 (12)	0.0482 (11)	0.0595 (15)	−0.0112 (10)	−0.0074 (11)	−0.0049 (10)
C2I	0.066 (6)	0.062 (5)	0.078 (7)	−0.028 (4)	−0.023 (5)	0.021 (5)
C1J	0.045 (5)	0.028 (4)	0.096 (7)	−0.006 (3)	0.010 (5)	−0.001 (4)
O1J	0.035 (3)	0.042 (3)	0.065 (4)	−0.011 (2)	0.018 (3)	−0.008 (2)
S1J	0.0460 (12)	0.0443 (11)	0.0618 (15)	−0.0159 (9)	0.0030 (11)	−0.0032 (10)
C2J	0.041 (5)	0.055 (5)	0.088 (7)	−0.016 (4)	0.002 (5)	−0.017 (4)

Geometric parameters (Å, º)

N1A—C2A	1.353 (7)	N3D—C4D	1.350 (8)
N1A—C8AA	1.366 (7)	C4D—N4D	1.322 (7)
N1A—H1XA	0.8800	C4D—C4AD	1.444 (8)
C2A—N2A	1.332 (8)	C4AD—N5D	1.351 (7)
C2A—N3A	1.348 (7)	C4AD—C8AD	1.398 (8)
N2A—H3A	0.8800	N5D—C6D	1.325 (7)
N2A—H2A	0.8800	N8D—C8AD	1.346 (7)
N3A—C4A	1.349 (7)	N8D—C7D	1.351 (7)
C4A—N4A	1.302 (7)	N2D—H3D	0.8800
C4A—C4AA	1.451 (8)	N2D—H2D	0.8800
N4A—H4A	0.8800	N4D—H4D	0.8800
N4A—H5A	0.8800	N4D—H5D	0.8800
C4AA—N5A	1.359 (7)	C6D—C7D	1.455 (8)
C4AA—C8AA	1.366 (8)	C6D—C9D	1.466 (8)
N5A—C6A	1.317 (7)	C7D—N7D	1.339 (7)
C6A—C7A	1.436 (8)	N7D—H7D	0.8800
C6A—C9A	1.493 (8)	N7D—H6D	0.8800
C7A—N7A	1.340 (7)	C9D—C10D	1.392 (9)
C7A—N8A	1.355 (8)	C9D—C14D	1.395 (8)
N7A—H7A	0.8800	C10D—C11D	1.384 (9)
N7A—H6A	0.8800	C10D—H10D	0.9500
N8A—C8AA	1.357 (7)	C11D—C12D	1.388 (9)
C9A—C14A	1.383 (8)	C11D—H11D	0.9500
C9A—C10A	1.400 (9)	C12D—C13D	1.390 (9)
C10A—C11A	1.384 (9)	C12D—H12D	0.9500
C10A—H10A	0.9500	C13D—C14D	1.368 (9)
C11A—C12A	1.377 (9)	C13D—H13D	0.9500
C11A—H11A	0.9500	C14D—H14D	0.9500
C12A—C13A	1.355 (9)	C1E—O1E	1.246 (8)
C12A—H12A	0.9500	C1E—O2E	1.271 (8)
C13A—C14A	1.380 (9)	C1E—C2E	1.516 (8)
C13A—H13A	0.9500	C2E—C3E	1.566 (9)
C14A—H14A	0.9500	C2E—H2E	0.9900
N1B—C2B	1.361 (7)	C2E—H3E	0.9900
N1B—C8AB	1.362 (7)	C3E—C4E	1.474 (9)
N1B—H1XB	0.8800	C3E—H4E	0.9900
C2B—N2B	1.295 (8)	C3E—H5E	0.9900
C2B—N3B	1.346 (7)	O3E—C7E	1.259 (8)
N2B—H3B	0.8800	C4E—C5E	1.536 (9)
N2B—H2B	0.8800	C4E—H6E	0.9900
N3B—C4B	1.357 (8)	C4E—H7E	0.9900
C4B—N4B	1.341 (7)	O4E—C7E	1.260 (7)
C4B—C4AB	1.426 (8)	C5E—C6E	1.540 (9)
N4B—H4B	0.8800	C5E—H8E	0.9900
N4B—H5B	0.8800	C5E—H9E	0.9900
C4AB—N5B	1.355 (7)	C6E—C7E	1.512 (9)
C4AB—C8AB	1.400 (8)	C6E—H10E	0.9900
N5B—C6B	1.316 (7)	C6E—H11E	0.9900
C6B—C9B	1.468 (9)	C1F—O1F	1.245 (7)
C6B—C7B	1.475 (8)	C1F—O2F	1.264 (7)
C7B—N8B	1.312 (8)	C1F—C2F	1.525 (8)
C7B—N7B	1.335 (7)	C2F—C3F	1.510 (8)
N7B—H7B	0.8800	C2F—H2F	0.9900
N7B—H6B	0.8800	C2F—H3F	0.9900
N8B—C8AB	1.343 (7)	C3F—C4F	1.541 (8)
C9B—C14B	1.385 (9)	C3F—H4F	0.9900
C9B—C10B	1.396 (9)	C3F—H5F	0.9900
C10B—C11B	1.375 (9)	O3F—C7F	1.261 (8)
C10B—H10B	0.9500	C4F—C5F	1.523 (9)
C11B—C12B	1.402 (9)	C4F—H6F	0.9900
C11B—H11B	0.9500	C4F—H7F	0.9900
C12B—C13B	1.378 (10)	O4F—C7F	1.261 (8)
C12B—H12B	0.9500	C5F—C6F	1.530 (9)
C13B—C14B	1.371 (9)	C5F—H8F	0.9900
C13B—H13B	0.9500	C5F—H9F	0.9900
C14B—H14B	0.9500	C6F—C7F	1.516 (8)
N1C—C8AC	1.367 (7)	C6F—H10F	0.9900
N1C—C2C	1.384 (7)	C6F—H11F	0.9900
N1C—H1XC	0.8800	C1G—S1G	1.776 (7)
C2C—N2C	1.308 (8)	C1G—H1G	0.9800
C2C—N3C	1.352 (7)	C1G—H2G	0.9800
N3C—C4C	1.339 (7)	C1G—H3G	0.9800
C4C—N4C	1.333 (7)	O1G—S1G	1.489 (4)
C4C—C4AC	1.427 (8)	S1G—C2G	1.776 (7)
C4AC—C8AC	1.369 (7)	C2G—H4G	0.9800
C4AC—N5C	1.381 (7)	C2G—H5G	0.9800
N5C—C6C	1.312 (7)	C2G—H6G	0.9800
N8C—C8AC	1.336 (7)	C1H—S1H	1.796 (7)
N8C—C7C	1.365 (8)	C1H—H4H	0.9800
N2C—H3C	0.8800	C1H—H5H	0.9800
N2C—H2C	0.8800	C1H—H6H	0.9800
N4C—H4C	0.8800	O1H—S1H	1.499 (4)
N4C—H5C	0.8800	S1H—C2H	1.775 (6)
C6C—C7C	1.442 (8)	C2H—H1H	0.9800
C6C—C9C	1.477 (9)	C2H—H2H	0.9800
C7C—N7C	1.343 (7)	C2H—H3H	0.9800
N7C—H7C	0.8800	C1I—S1I	1.766 (7)
N7C—H6C	0.8800	C1I—H1I	0.9800
C9C—C10C	1.380 (8)	C1I—H2I	0.9800
C9C—C14C	1.420 (8)	C1I—H3I	0.9800
C10C—C11C	1.374 (9)	O1I—S1I	1.523 (4)
C10C—H10C	0.9500	S1I—C2I	1.777 (7)
C11C—C12C	1.374 (9)	C2I—H4I	0.9800
C11C—H11C	0.9500	C2I—H5I	0.9800
C12C—C13C	1.383 (9)	C2I—H6I	0.9800
C12C—H12C	0.9500	C1J—S1J	1.793 (6)
C13C—C14C	1.379 (9)	C1J—H1J	0.9800
C13C—H13C	0.9500	C1J—H2J	0.9800
C14C—H14C	0.9500	C1J—H3J	0.9800
N1D—C8AD	1.365 (7)	O1J—S1J	1.515 (4)
N1D—C2D	1.366 (7)	S1J—C2J	1.757 (7)
N1D—H1XD	0.8800	C2J—H4J	0.9800
C2D—N2D	1.327 (7)	C2J—H5J	0.9800
C2D—N3D	1.329 (7)	C2J—H6J	0.9800
C2A—N1A—C8AA	119.6 (5)	C2D—N2D—H3D	120.0
C2A—N1A—H1XA	120.2	C2D—N2D—H2D	120.0
C8AA—N1A—H1XA	120.2	H3D—N2D—H2D	120.0
N2A—C2A—N3A	118.8 (6)	C4D—N4D—H4D	120.0
N2A—C2A—N1A	117.5 (6)	C4D—N4D—H5D	120.0
N3A—C2A—N1A	123.7 (6)	H4D—N4D—H5D	120.0
C2A—N2A—H3A	120.0	N5D—C6D—C7D	119.3 (6)
C2A—N2A—H2A	120.0	N5D—C6D—C9D	118.8 (5)
H3A—N2A—H2A	120.0	C7D—C6D—C9D	121.8 (5)
C2A—N3A—C4A	118.4 (5)	N7D—C7D—N8D	116.8 (5)
N4A—C4A—N3A	119.3 (5)	N7D—C7D—C6D	121.0 (6)
N4A—C4A—C4AA	121.0 (6)	N8D—C7D—C6D	122.2 (5)
N3A—C4A—C4AA	119.7 (5)	C7D—N7D—H7D	120.0
C4A—N4A—H4A	120.0	C7D—N7D—H6D	120.0
C4A—N4A—H5A	120.0	H7D—N7D—H6D	120.0
H4A—N4A—H5A	120.0	N8D—C8AD—N1D	117.7 (5)
N5A—C4AA—C8AA	122.2 (5)	N8D—C8AD—C4AD	122.9 (6)
N5A—C4AA—C4A	118.8 (5)	N1D—C8AD—C4AD	119.3 (5)
C8AA—C4AA—C4A	118.8 (6)	C10D—C9D—C14D	117.3 (6)
C6A—N5A—C4AA	117.2 (5)	C10D—C9D—C6D	123.7 (6)
N5A—C6A—C7A	120.6 (6)	C14D—C9D—C6D	119.0 (6)
N5A—C6A—C9A	115.4 (5)	C11D—C10D—C9D	120.9 (6)
C7A—C6A—C9A	123.9 (5)	C11D—C10D—H10D	119.5
N7A—C7A—N8A	115.5 (5)	C9D—C10D—H10D	119.5
N7A—C7A—C6A	122.2 (6)	C10D—C11D—C12D	120.4 (7)
N8A—C7A—C6A	122.3 (5)	C10D—C11D—H11D	119.8
C7A—N7A—H7A	120.0	C12D—C11D—H11D	119.8
C7A—N7A—H6A	120.0	C11D—C12D—C13D	119.1 (7)
H7A—N7A—H6A	120.0	C11D—C12D—H12D	120.4
C7A—N8A—C8AA	114.6 (5)	C13D—C12D—H12D	120.4
N8A—C8AA—N1A	117.4 (5)	C14D—C13D—C12D	119.7 (7)
N8A—C8AA—C4AA	123.1 (6)	C14D—C13D—H13D	120.1
N1A—C8AA—C4AA	119.5 (5)	C12D—C13D—H13D	120.1
C14A—C9A—C10A	118.8 (6)	C13D—C14D—C9D	122.3 (7)
C14A—C9A—C6A	118.2 (6)	C13D—C14D—H14D	118.9
C10A—C9A—C6A	123.0 (6)	C9D—C14D—H14D	118.9
C11A—C10A—C9A	119.7 (6)	O1E—C1E—O2E	122.7 (6)
C11A—C10A—H10A	120.1	O1E—C1E—C2E	118.9 (6)
C9A—C10A—H10A	120.1	O2E—C1E—C2E	118.4 (7)
C12A—C11A—C10A	120.6 (7)	C1E—C2E—C3E	111.3 (6)
C12A—C11A—H11A	119.7	C1E—C2E—H2E	109.4
C10A—C11A—H11A	119.7	C3E—C2E—H2E	109.4
C13A—C12A—C11A	119.5 (7)	C1E—C2E—H3E	109.4
C13A—C12A—H12A	120.3	C3E—C2E—H3E	109.4
C11A—C12A—H12A	120.3	H2E—C2E—H3E	108.0
C12A—C13A—C14A	121.4 (7)	C4E—C3E—C2E	115.5 (6)
C12A—C13A—H13A	119.3	C4E—C3E—H4E	108.4
C14A—C13A—H13A	119.3	C2E—C3E—H4E	108.4
C13A—C14A—C9A	120.1 (7)	C4E—C3E—H5E	108.4
C13A—C14A—H14A	120.0	C2E—C3E—H5E	108.4
C9A—C14A—H14A	120.0	H4E—C3E—H5E	107.5
C2B—N1B—C8AB	121.4 (5)	C3E—C4E—C5E	111.8 (6)
C2B—N1B—H1XB	119.3	C3E—C4E—H6E	109.2
C8AB—N1B—H1XB	119.3	C5E—C4E—H6E	109.2
N2B—C2B—N3B	119.0 (6)	C3E—C4E—H7E	109.2
N2B—C2B—N1B	118.5 (6)	C5E—C4E—H7E	109.2
N3B—C2B—N1B	122.5 (6)	H6E—C4E—H7E	107.9
C2B—N2B—H3B	120.0	C4E—C5E—C6E	115.6 (6)
C2B—N2B—H2B	120.0	C4E—C5E—H8E	108.4
H3B—N2B—H2B	120.0	C6E—C5E—H8E	108.4
C2B—N3B—C4B	117.9 (5)	C4E—C5E—H9E	108.4
N4B—C4B—N3B	117.1 (5)	C6E—C5E—H9E	108.4
N4B—C4B—C4AB	121.2 (6)	H8E—C5E—H9E	107.4
N3B—C4B—C4AB	121.7 (6)	C7E—C6E—C5E	114.3 (6)
C4B—N4B—H4B	120.0	C7E—C6E—H10E	108.7
C4B—N4B—H5B	120.0	C5E—C6E—H10E	108.7
H4B—N4B—H5B	120.0	C7E—C6E—H11E	108.7
N5B—C4AB—C8AB	120.6 (5)	C5E—C6E—H11E	108.7
N5B—C4AB—C4B	121.5 (5)	H10E—C6E—H11E	107.6
C8AB—C4AB—C4B	117.9 (6)	O3E—C7E—O4E	124.1 (6)
C6B—N5B—C4AB	119.3 (5)	O3E—C7E—C6E	117.5 (6)
N5B—C6B—C9B	119.0 (5)	O4E—C7E—C6E	118.2 (7)
N5B—C6B—C7B	118.6 (6)	O1F—C1F—O2F	124.9 (6)
C9B—C6B—C7B	122.3 (5)	O1F—C1F—C2F	118.6 (6)
N8B—C7B—N7B	118.2 (5)	O2F—C1F—C2F	116.5 (6)
N8B—C7B—C6B	121.9 (5)	C3F—C2F—C1F	115.1 (5)
N7B—C7B—C6B	119.8 (6)	C3F—C2F—H2F	108.5
C7B—N7B—H7B	120.0	C1F—C2F—H2F	108.5
C7B—N7B—H6B	120.0	C3F—C2F—H3F	108.5
H7B—N7B—H6B	120.0	C1F—C2F—H3F	108.5
C7B—N8B—C8AB	117.5 (5)	H2F—C2F—H3F	107.5
N8B—C8AB—N1B	119.7 (5)	C2F—C3F—C4F	115.1 (5)
N8B—C8AB—C4AB	121.9 (6)	C2F—C3F—H4F	108.5
N1B—C8AB—C4AB	118.4 (5)	C4F—C3F—H4F	108.5
C14B—C9B—C10B	117.4 (6)	C2F—C3F—H5F	108.5
C14B—C9B—C6B	119.1 (6)	C4F—C3F—H5F	108.5
C10B—C9B—C6B	123.4 (6)	H4F—C3F—H5F	107.5
C11B—C10B—C9B	120.7 (7)	C5F—C4F—C3F	112.9 (5)
C11B—C10B—H10B	119.6	C5F—C4F—H6F	109.0
C9B—C10B—H10B	119.6	C3F—C4F—H6F	109.0
C10B—C11B—C12B	119.9 (7)	C5F—C4F—H7F	109.0
C10B—C11B—H11B	120.1	C3F—C4F—H7F	109.0
C12B—C11B—H11B	120.1	H6F—C4F—H7F	107.8
C13B—C12B—C11B	120.3 (7)	C4F—C5F—C6F	115.0 (5)
C13B—C12B—H12B	119.9	C4F—C5F—H8F	108.5
C11B—C12B—H12B	119.9	C6F—C5F—H8F	108.5
C14B—C13B—C12B	118.4 (7)	C4F—C5F—H9F	108.5
C14B—C13B—H13B	120.8	C6F—C5F—H9F	108.5
C12B—C13B—H13B	120.8	H8F—C5F—H9F	107.5
C13B—C14B—C9B	123.3 (7)	C7F—C6F—C5F	116.1 (5)
C13B—C14B—H14B	118.3	C7F—C6F—H10F	108.3
C9B—C14B—H14B	118.3	C5F—C6F—H10F	108.3
C8AC—N1C—C2C	119.6 (5)	C7F—C6F—H11F	108.3
C8AC—N1C—H1XC	120.2	C5F—C6F—H11F	108.3
C2C—N1C—H1XC	120.2	H10F—C6F—H11F	107.4
N2C—C2C—N3C	119.3 (5)	O4F—C7F—O3F	125.1 (6)
N2C—C2C—N1C	118.0 (6)	O4F—C7F—C6F	116.1 (6)
N3C—C2C—N1C	122.6 (6)	O3F—C7F—C6F	118.8 (7)
C4C—N3C—C2C	118.3 (5)	S1G—C1G—H1G	109.5
N4C—C4C—N3C	118.1 (5)	S1G—C1G—H2G	109.5
N4C—C4C—C4AC	121.5 (6)	H1G—C1G—H2G	109.5
N3C—C4C—C4AC	120.5 (5)	S1G—C1G—H3G	109.5
C8AC—C4AC—N5C	120.3 (5)	H1G—C1G—H3G	109.5
C8AC—C4AC—C4C	120.2 (6)	H2G—C1G—H3G	109.5
N5C—C4AC—C4C	119.5 (5)	O1G—S1G—C2G	105.5 (3)
C6C—N5C—C4AC	118.8 (5)	O1G—S1G—C1G	105.5 (3)
C8AC—N8C—C7C	115.6 (5)	C2G—S1G—C1G	98.3 (4)
C2C—N2C—H3C	120.0	S1G—C2G—H4G	109.5
C2C—N2C—H2C	120.0	S1G—C2G—H5G	109.5
H3C—N2C—H2C	120.0	H4G—C2G—H5G	109.5
C4C—N4C—H4C	120.0	S1G—C2G—H6G	109.5
C4C—N4C—H5C	120.0	H4G—C2G—H6G	109.5
H4C—N4C—H5C	120.0	H5G—C2G—H6G	109.5
N5C—C6C—C7C	119.6 (6)	S1H—C1H—H4H	109.5
N5C—C6C—C9C	115.8 (5)	S1H—C1H—H5H	109.5
C7C—C6C—C9C	124.6 (5)	H4H—C1H—H5H	109.5
N7C—C7C—N8C	116.2 (5)	S1H—C1H—H6H	109.5
N7C—C7C—C6C	122.0 (6)	H4H—C1H—H6H	109.5
N8C—C7C—C6C	121.8 (5)	H5H—C1H—H6H	109.5
C7C—N7C—H7C	120.0	O1H—S1H—C2H	106.1 (3)
C7C—N7C—H6C	120.0	O1H—S1H—C1H	105.2 (3)
H7C—N7C—H6C	120.0	C2H—S1H—C1H	97.0 (3)
N8C—C8AC—N1C	117.8 (5)	S1H—C2H—H1H	109.5
N8C—C8AC—C4AC	123.8 (6)	S1H—C2H—H2H	109.5
N1C—C8AC—C4AC	118.4 (5)	H1H—C2H—H2H	109.5
C10C—C9C—C14C	117.0 (6)	S1H—C2H—H3H	109.5
C10C—C9C—C6C	125.4 (6)	H1H—C2H—H3H	109.5
C14C—C9C—C6C	117.5 (6)	H2H—C2H—H3H	109.5
C11C—C10C—C9C	122.8 (6)	S1I—C1I—H1I	109.5
C11C—C10C—H10C	118.6	S1I—C1I—H2I	109.5
C9C—C10C—H10C	118.6	H1I—C1I—H2I	109.5
C10C—C11C—C12C	119.5 (7)	S1I—C1I—H3I	109.5
C10C—C11C—H11C	120.2	H1I—C1I—H3I	109.5
C12C—C11C—H11C	120.2	H2I—C1I—H3I	109.5
C11C—C12C—C13C	119.8 (7)	O1I—S1I—C1I	105.8 (3)
C11C—C12C—H12C	120.1	O1I—S1I—C2I	105.3 (3)
C13C—C12C—H12C	120.1	C1I—S1I—C2I	98.3 (4)
C14C—C13C—C12C	120.7 (7)	S1I—C2I—H4I	109.5
C14C—C13C—H13C	119.6	S1I—C2I—H5I	109.5
C12C—C13C—H13C	119.6	H4I—C2I—H5I	109.5
C13C—C14C—C9C	120.2 (6)	S1I—C2I—H6I	109.5
C13C—C14C—H14C	119.9	H4I—C2I—H6I	109.5
C9C—C14C—H14C	119.9	H5I—C2I—H6I	109.5
C8AD—N1D—C2D	119.4 (5)	S1J—C1J—H1J	109.5
C8AD—N1D—H1XD	120.3	S1J—C1J—H2J	109.5
C2D—N1D—H1XD	120.3	H1J—C1J—H2J	109.5
N2D—C2D—N3D	118.3 (5)	S1J—C1J—H3J	109.5
N2D—C2D—N1D	117.3 (5)	H1J—C1J—H3J	109.5
N3D—C2D—N1D	124.4 (6)	H2J—C1J—H3J	109.5
C2D—N3D—C4D	118.0 (5)	O1J—S1J—C2J	105.8 (3)
N4D—C4D—N3D	118.6 (5)	O1J—S1J—C1J	107.0 (3)
N4D—C4D—C4AD	120.3 (6)	C2J—S1J—C1J	97.4 (4)
N3D—C4D—C4AD	121.1 (5)	S1J—C2J—H4J	109.5
N5D—C4AD—C8AD	120.9 (5)	S1J—C2J—H5J	109.5
N5D—C4AD—C4D	121.5 (5)	H4J—C2J—H5J	109.5
C8AD—C4AD—C4D	117.6 (6)	S1J—C2J—H6J	109.5
C6D—N5D—C4AD	118.9 (5)	H4J—C2J—H6J	109.5
C8AD—N8D—C7D	115.7 (5)	H5J—C2J—H6J	109.5
C8AA—N1A—C2A—N2A	175.1 (6)	N4C—C4C—C4AC—N5C	−2.2 (9)
C8AA—N1A—C2A—N3A	−4.9 (9)	N3C—C4C—C4AC—N5C	178.6 (6)
N2A—C2A—N3A—C4A	−176.0 (6)	C8AC—C4AC—N5C—C6C	0.2 (9)
N1A—C2A—N3A—C4A	4.0 (10)	C4C—C4AC—N5C—C6C	−178.6 (6)
C2A—N3A—C4A—N4A	−179.6 (6)	C4AC—N5C—C6C—C7C	−0.9 (9)
C2A—N3A—C4A—C4AA	0.6 (9)	C4AC—N5C—C6C—C9C	−179.6 (6)
N4A—C4A—C4AA—N5A	0.3 (9)	C8AC—N8C—C7C—N7C	−176.5 (5)
N3A—C4A—C4AA—N5A	−179.9 (6)	C8AC—N8C—C7C—C6C	3.5 (9)
N4A—C4A—C4AA—C8AA	175.9 (6)	N5C—C6C—C7C—N7C	179.0 (6)
N3A—C4A—C4AA—C8AA	−4.3 (9)	C9C—C6C—C7C—N7C	−2.4 (10)
C8AA—C4AA—N5A—C6A	1.3 (9)	N5C—C6C—C7C—N8C	−1.0 (10)
C4A—C4AA—N5A—C6A	176.8 (6)	C9C—C6C—C7C—N8C	177.6 (6)
C4AA—N5A—C6A—C7A	−1.4 (9)	C7C—N8C—C8AC—N1C	178.8 (6)
C4AA—N5A—C6A—C9A	−177.7 (5)	C7C—N8C—C8AC—C4AC	−4.3 (9)
N5A—C6A—C7A—N7A	179.8 (6)	C2C—N1C—C8AC—N8C	−177.3 (5)
C9A—C6A—C7A—N7A	−4.3 (10)	C2C—N1C—C8AC—C4AC	5.6 (9)
N5A—C6A—C7A—N8A	1.2 (9)	N5C—C4AC—C8AC—N8C	2.6 (9)
C9A—C6A—C7A—N8A	177.1 (6)	C4C—C4AC—C8AC—N8C	−178.6 (6)
N7A—C7A—N8A—C8AA	−179.4 (5)	N5C—C4AC—C8AC—N1C	179.5 (5)
C6A—C7A—N8A—C8AA	−0.7 (9)	C4C—C4AC—C8AC—N1C	−1.8 (9)
C7A—N8A—C8AA—N1A	−179.3 (5)	N5C—C6C—C9C—C10C	138.6 (6)
C7A—N8A—C8AA—C4AA	0.5 (9)	C7C—C6C—C9C—C10C	−40.1 (10)
C2A—N1A—C8AA—N8A	−179.3 (6)	N5C—C6C—C9C—C14C	−36.6 (8)
C2A—N1A—C8AA—C4AA	0.9 (9)	C7C—C6C—C9C—C14C	144.8 (6)
N5A—C4AA—C8AA—N8A	−0.9 (10)	C14C—C9C—C10C—C11C	−1.2 (9)
C4A—C4AA—C8AA—N8A	−176.4 (6)	C6C—C9C—C10C—C11C	−176.3 (6)
N5A—C4AA—C8AA—N1A	178.9 (6)	C9C—C10C—C11C—C12C	1.6 (10)
C4A—C4AA—C8AA—N1A	3.4 (9)	C10C—C11C—C12C—C13C	−1.1 (10)
N5A—C6A—C9A—C14A	−41.6 (8)	C11C—C12C—C13C—C14C	0.4 (10)
C7A—C6A—C9A—C14A	142.3 (6)	C12C—C13C—C14C—C9C	0.0 (10)
N5A—C6A—C9A—C10A	134.9 (6)	C10C—C9C—C14C—C13C	0.4 (9)
C7A—C6A—C9A—C10A	−41.2 (9)	C6C—C9C—C14C—C13C	175.9 (6)
C14A—C9A—C10A—C11A	−0.4 (10)	C8AD—N1D—C2D—N2D	178.7 (6)
C6A—C9A—C10A—C11A	−176.8 (6)	C8AD—N1D—C2D—N3D	−4.4 (9)
C9A—C10A—C11A—C12A	−1.0 (10)	N2D—C2D—N3D—C4D	−176.9 (6)
C10A—C11A—C12A—C13A	1.2 (10)	N1D—C2D—N3D—C4D	6.2 (9)
C11A—C12A—C13A—C14A	0.0 (10)	C2D—N3D—C4D—N4D	177.1 (6)
C12A—C13A—C14A—C9A	−1.3 (10)	C2D—N3D—C4D—C4AD	−4.2 (9)
C10A—C9A—C14A—C13A	1.5 (10)	N4D—C4D—C4AD—N5D	−0.1 (10)
C6A—C9A—C14A—C13A	178.1 (5)	N3D—C4D—C4AD—N5D	−178.8 (6)
C8AB—N1B—C2B—N2B	179.2 (6)	N4D—C4D—C4AD—C8AD	179.3 (6)
C8AB—N1B—C2B—N3B	−2.6 (9)	N3D—C4D—C4AD—C8AD	0.6 (9)
N2B—C2B—N3B—C4B	−177.6 (6)	C8AD—C4AD—N5D—C6D	−1.1 (9)
N1B—C2B—N3B—C4B	4.2 (9)	C4D—C4AD—N5D—C6D	178.2 (6)
C2B—N3B—C4B—N4B	177.7 (6)	C4AD—N5D—C6D—C7D	2.6 (9)
C2B—N3B—C4B—C4AB	−3.0 (9)	C4AD—N5D—C6D—C9D	179.1 (6)
N4B—C4B—C4AB—N5B	1.6 (9)	C8AD—N8D—C7D—N7D	−179.5 (5)
N3B—C4B—C4AB—N5B	−177.7 (6)	C8AD—N8D—C7D—C6D	−2.1 (9)
N4B—C4B—C4AB—C8AB	179.5 (6)	N5D—C6D—C7D—N7D	176.3 (6)
N3B—C4B—C4AB—C8AB	0.2 (9)	C9D—C6D—C7D—N7D	−0.1 (9)
C8AB—C4AB—N5B—C6B	−1.4 (9)	N5D—C6D—C7D—N8D	−0.9 (9)
C4B—C4AB—N5B—C6B	176.5 (6)	C9D—C6D—C7D—N8D	−177.4 (6)
C4AB—N5B—C6B—C9B	178.8 (6)	C7D—N8D—C8AD—N1D	−179.2 (6)
C4AB—N5B—C6B—C7B	3.2 (9)	C7D—N8D—C8AD—C4AD	3.7 (9)
N5B—C6B—C7B—N8B	−3.2 (9)	C2D—N1D—C8AD—N8D	−176.9 (5)
C9B—C6B—C7B—N8B	−178.6 (6)	C2D—N1D—C8AD—C4AD	0.4 (9)
N5B—C6B—C7B—N7B	176.1 (6)	N5D—C4AD—C8AD—N8D	−2.2 (10)
C9B—C6B—C7B—N7B	0.7 (9)	C4D—C4AD—C8AD—N8D	178.4 (6)
N7B—C7B—N8B—C8AB	−178.3 (6)	N5D—C4AD—C8AD—N1D	−179.3 (6)
C6B—C7B—N8B—C8AB	0.9 (9)	C4D—C4AD—C8AD—N1D	1.3 (9)
C7B—N8B—C8AB—N1B	−179.2 (6)	N5D—C6D—C9D—C10D	131.4 (6)
C7B—N8B—C8AB—C4AB	1.1 (9)	C7D—C6D—C9D—C10D	−52.1 (9)
C2B—N1B—C8AB—N8B	180.0 (6)	N5D—C6D—C9D—C14D	−46.3 (9)
C2B—N1B—C8AB—C4AB	−0.4 (9)	C7D—C6D—C9D—C14D	130.2 (6)
N5B—C4AB—C8AB—N8B	−1.0 (10)	C14D—C9D—C10D—C11D	1.8 (9)
C4B—C4AB—C8AB—N8B	−178.9 (6)	C6D—C9D—C10D—C11D	−175.9 (6)
N5B—C4AB—C8AB—N1B	179.4 (6)	C9D—C10D—C11D—C12D	−2.4 (10)
C4B—C4AB—C8AB—N1B	1.4 (9)	C10D—C11D—C12D—C13D	−0.2 (10)
N5B—C6B—C9B—C14B	−44.2 (9)	C11D—C12D—C13D—C14D	3.3 (10)
C7B—C6B—C9B—C14B	131.2 (6)	C12D—C13D—C14D—C9D	−3.9 (10)
N5B—C6B—C9B—C10B	133.1 (6)	C10D—C9D—C14D—C13D	1.4 (9)
C7B—C6B—C9B—C10B	−51.5 (9)	C6D—C9D—C14D—C13D	179.2 (6)
C14B—C9B—C10B—C11B	1.0 (9)	O1E—C1E—C2E—C3E	161.3 (6)
C6B—C9B—C10B—C11B	−176.3 (6)	O2E—C1E—C2E—C3E	−20.6 (9)
C9B—C10B—C11B—C12B	−2.3 (9)	C1E—C2E—C3E—C4E	−179.0 (6)
C10B—C11B—C12B—C13B	1.6 (10)	C2E—C3E—C4E—C5E	175.1 (6)
C11B—C12B—C13B—C14B	0.4 (10)	C3E—C4E—C5E—C6E	58.4 (8)
C12B—C13B—C14B—C9B	−1.8 (10)	C4E—C5E—C6E—C7E	64.4 (8)
C10B—C9B—C14B—C13B	1.1 (10)	C5E—C6E—C7E—O3E	−162.5 (6)
C6B—C9B—C14B—C13B	178.5 (6)	C5E—C6E—C7E—O4E	22.8 (8)
C8AC—N1C—C2C—N2C	175.4 (6)	O1F—C1F—C2F—C3F	171.8 (6)
C8AC—N1C—C2C—N3C	−7.9 (9)	O2F—C1F—C2F—C3F	−6.7 (8)
N2C—C2C—N3C—C4C	−177.4 (6)	C1F—C2F—C3F—C4F	−177.8 (5)
N1C—C2C—N3C—C4C	6.0 (9)	C2F—C3F—C4F—C5F	176.3 (6)
C2C—N3C—C4C—N4C	178.9 (5)	C3F—C4F—C5F—C6F	64.9 (7)
C2C—N3C—C4C—C4AC	−1.9 (9)	C4F—C5F—C6F—C7F	68.3 (7)
N4C—C4C—C4AC—C8AC	179.1 (6)	C5F—C6F—C7F—O4F	−165.8 (6)
N3C—C4C—C4AC—C8AC	−0.1 (9)	C5F—C6F—C7F—O3F	15.7 (9)

Triamterenium azelate, DMSO solvate (1e_DMSO)

Crystal data

2(C12H12N7^+)·C9H14O4^2^−·2(C2H6OS)	F(000) = 1800
Mr = 851.03	Dx = 1.384 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.7107 Å
a = 15.0338 (3) Å	Cell parameters from 13200 reflections
b = 11.5004 (2) Å	θ = 1.0–25.4°
c = 24.3960 (6) Å	µ = 0.20 mm^−1
β = 104.539 (1)°	T = 180 K
V = 4082.87 (15) Å^3	Block, colourless
Z = 4	0.14 × 0.10 × 0.05 mm

Data collection

Nonius Kappa CCD diffractometer	7406 independent reflections
Radiation source: fine-focus sealed tube	4611 reflections with I > 2σ(I)
None monochromator	Rint = 0.047
Thin slice ω and φ scans	θmax = 25.4°, θmin = 3.5°
Absorption correction: multi-scan multi-scan from symmetry-related measurements Sortav (Blessing 1995)	h = −18→17
Tmin = 0.932, Tmax = 0.997	k = −13→13
22149 measured reflections	l = −27→29

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.059	Hydrogen site location: mixed
wR(F^2) = 0.163	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.095P)^2 + 0.204P] where P = (Fo^2 + 2Fc^2)/3
7406 reflections	(Δ/σ)max < 0.001
705 parameters	Δρmax = 1.26 e Å^−3
0 restraints	Δρmin = −0.40 e Å^−3

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
N1A	−0.00745 (17)	0.6306 (2)	0.03372 (11)	0.0350 (6)
C2A	0.0642 (2)	0.6587 (2)	0.01120 (12)	0.0350 (7)
N2A	0.0485 (2)	0.7337 (3)	−0.03070 (12)	0.0450 (7)
N3A	0.14916 (16)	0.6127 (2)	0.03002 (10)	0.0357 (6)
C4A	0.16405 (19)	0.5376 (2)	0.07309 (12)	0.0317 (7)
N4A	0.24705 (18)	0.4922 (2)	0.09131 (12)	0.0358 (6)
C4AA	0.09218 (19)	0.5057 (2)	0.09875 (12)	0.0328 (7)
N5A	0.10906 (16)	0.43285 (19)	0.14390 (10)	0.0327 (6)
C6A	0.0409 (2)	0.4052 (2)	0.16608 (12)	0.0332 (7)
C7A	−0.05082 (19)	0.4500 (2)	0.14116 (12)	0.0318 (7)
N7A	−0.1221 (2)	0.4141 (2)	0.15987 (13)	0.0402 (7)
N8A	−0.06718 (16)	0.52609 (19)	0.09838 (10)	0.0335 (6)
C8AA	0.0052 (2)	0.5542 (2)	0.07765 (12)	0.0334 (7)
C9A	0.06145 (19)	0.3236 (2)	0.21485 (12)	0.0341 (7)
C10A	0.0303 (2)	0.3422 (3)	0.26338 (14)	0.0435 (8)
C11A	0.0523 (2)	0.2623 (3)	0.30757 (15)	0.0538 (9)
C12A	0.1044 (2)	0.1665 (3)	0.30407 (15)	0.0491 (9)
C13A	0.1367 (2)	0.1477 (3)	0.25632 (15)	0.0447 (8)
C14A	0.1158 (2)	0.2269 (3)	0.21185 (14)	0.0378 (7)
N1B	0.52477 (17)	0.4847 (2)	0.11282 (10)	0.0302 (6)
C2B	0.61363 (19)	0.4517 (2)	0.13193 (12)	0.0307 (7)
N2B	0.6333 (2)	0.3808 (2)	0.17591 (12)	0.0408 (7)
N3B	0.68140 (15)	0.48655 (19)	0.10902 (10)	0.0306 (5)
C4B	0.66074 (19)	0.5636 (2)	0.06628 (12)	0.0295 (6)
N4B	0.72793 (18)	0.5977 (2)	0.04347 (11)	0.0346 (6)
C4AB	0.56957 (18)	0.6097 (2)	0.04682 (11)	0.0277 (6)
N5B	0.55136 (15)	0.69763 (19)	0.00862 (9)	0.0299 (5)
C6B	0.46703 (19)	0.7379 (2)	−0.00669 (11)	0.0298 (6)
C7B	0.39429 (19)	0.6841 (2)	0.01374 (11)	0.0287 (6)
N7B	0.30704 (18)	0.7141 (2)	−0.00632 (12)	0.0362 (6)
C8AB	0.50110 (19)	0.5661 (2)	0.07066 (11)	0.0272 (6)
N8B	0.41325 (15)	0.59965 (18)	0.05340 (9)	0.0290 (5)
C9B	0.45030 (19)	0.8408 (2)	−0.04485 (12)	0.0319 (7)
C10B	0.3980 (2)	0.9345 (3)	−0.03473 (14)	0.0370 (7)
C11B	0.3890 (2)	1.0330 (3)	−0.06838 (15)	0.0419 (8)
C12B	0.4318 (2)	1.0388 (3)	−0.11232 (17)	0.0535 (10)
C13B	0.4837 (2)	0.9462 (3)	−0.12258 (15)	0.0501 (9)
C14B	0.4939 (2)	0.8480 (3)	−0.08887 (13)	0.0389 (7)
C1C	0.4328 (2)	0.3134 (3)	0.20478 (14)	0.0452 (8)
O1C	0.40424 (14)	0.36829 (18)	0.15868 (9)	0.0432 (5)
C2C	0.3673 (3)	0.2281 (4)	0.22178 (15)	0.0610 (10)
H2C	0.3823	0.1487	0.2112	0.073*
H3C	0.3040	0.2461	0.1999	0.073*
O2C	0.51231 (16)	0.3203 (2)	0.23588 (10)	0.0606 (7)
C3C	0.3702 (3)	0.2296 (3)	0.28510 (15)	0.0480 (9)
O3C	0.33111 (14)	0.75697 (19)	0.49178 (9)	0.0485 (6)
C4C	0.3350 (3)	0.3422 (3)	0.3024 (2)	0.0611 (11)
O4C	0.3859 (2)	0.6685 (3)	0.42795 (16)	0.1124 (14)
C5C	0.3189 (3)	0.3418 (4)	0.3603 (2)	0.0738 (14)
C6C	0.2745 (4)	0.4656 (4)	0.3675 (2)	0.0847 (14)
C7C	0.2583 (4)	0.4816 (4)	0.4202 (3)	0.106 (2)
H12C	0.3115	0.4496	0.4487	0.127*
H13C	0.2041	0.4342	0.4218	0.127*
C8C	0.2415 (3)	0.6058 (3)	0.43845 (19)	0.0547 (10)
C9C	0.3257 (2)	0.6815 (3)	0.45415 (15)	0.0468 (8)
C1D	0.7034 (4)	0.0981 (4)	0.2403 (2)	0.0705 (13)
O1D	0.80316 (15)	0.28768 (17)	0.24377 (9)	0.0467 (6)
S1D	0.78812 (6)	0.19277 (7)	0.28283 (4)	0.0441 (2)
C2D	0.7163 (3)	0.2526 (4)	0.32355 (18)	0.0558 (10)
C1E	0.5638 (5)	0.4602 (5)	0.4135 (2)	0.130 (3)
H1E	0.5850	0.4475	0.4545	0.195*
H2E	0.5475	0.3854	0.3944	0.195*
H3E	0.5097	0.5111	0.4055	0.195*
O1E	0.67585 (16)	0.6382 (2)	0.41991 (11)	0.0663 (7)
S1E	0.65298 (6)	0.52674 (8)	0.38849 (5)	0.0652 (3)
C2E	0.5827 (5)	0.5600 (6)	0.3216 (2)	0.0913 (17)
H1XA	−0.060 (3)	0.669 (3)	0.0193 (14)	0.054 (10)*
H2A	−0.006 (3)	0.762 (3)	−0.0449 (16)	0.065 (12)*
H3A	0.091 (3)	0.750 (3)	−0.0426 (14)	0.047 (11)*
H4A	0.288 (2)	0.516 (2)	0.0753 (12)	0.025 (8)*
H5A	0.253 (2)	0.441 (3)	0.1149 (13)	0.031 (9)*
H6A	−0.114 (2)	0.359 (3)	0.1868 (14)	0.045 (9)*
H7A	−0.173 (3)	0.431 (3)	0.1446 (14)	0.040 (10)*
H10A	−0.008 (2)	0.409 (3)	0.2689 (13)	0.050 (9)*
H11A	0.029 (3)	0.277 (3)	0.3388 (16)	0.067 (11)*
H12A	0.118 (2)	0.114 (3)	0.3352 (15)	0.053 (10)*
H13A	0.177 (2)	0.075 (3)	0.2551 (14)	0.057 (10)*
H14A	0.135 (2)	0.212 (2)	0.1756 (13)	0.034 (8)*
H1XB	0.488 (2)	0.454 (3)	0.1282 (14)	0.043 (10)*
H2B	0.590 (3)	0.360 (3)	0.1939 (16)	0.065 (12)*
H3B	0.687 (2)	0.353 (3)	0.1886 (13)	0.035 (9)*
H4B	0.790 (3)	0.568 (3)	0.0570 (13)	0.045 (9)*
H5B	0.721 (3)	0.649 (3)	0.0164 (16)	0.062 (12)*
H6B	0.288 (2)	0.762 (3)	−0.0337 (15)	0.049 (10)*
H7B	0.264 (2)	0.683 (3)	0.0076 (13)	0.039 (9)*
H10B	0.370 (2)	0.930 (2)	−0.0027 (12)	0.032 (8)*
H11B	0.355 (2)	1.087 (3)	−0.0608 (12)	0.030 (8)*
H12B	0.422 (2)	1.104 (3)	−0.1356 (15)	0.058 (10)*
H13B	0.518 (3)	0.953 (3)	−0.1552 (16)	0.075 (12)*
H14B	0.5265 (19)	0.786 (2)	−0.0945 (11)	0.026 (7)*
H4C	0.438 (2)	0.216 (2)	0.3043 (12)	0.040 (8)*
H5C	0.331 (2)	0.158 (3)	0.2941 (14)	0.061 (10)*
H6C	0.378 (3)	0.409 (3)	0.3030 (15)	0.065 (11)*
H7C	0.271 (3)	0.363 (3)	0.2774 (14)	0.056 (10)*
H8C	0.375 (2)	0.319 (2)	0.3905 (12)	0.032 (8)*
H9C	0.273 (3)	0.277 (3)	0.3621 (14)	0.059 (10)*
H10C	0.320 (3)	0.535 (3)	0.3634 (15)	0.070 (11)*
H11C	0.202 (3)	0.473 (3)	0.3337 (19)	0.091 (13)*
H14C	0.211 (3)	0.607 (3)	0.4663 (18)	0.080 (13)*
H15C	0.190 (3)	0.657 (4)	0.4035 (19)	0.093 (14)*
H1D	0.728 (4)	0.062 (5)	0.209 (3)	0.14 (2)*
H2D	0.696 (3)	0.042 (4)	0.255 (2)	0.090 (18)*
H3D	0.648 (3)	0.144 (4)	0.2206 (17)	0.072 (13)*
H4D	0.659 (2)	0.291 (3)	0.2969 (14)	0.052 (9)*
H5D	0.706 (3)	0.196 (4)	0.3475 (17)	0.078 (14)*
H6D	0.750 (3)	0.313 (3)	0.3453 (16)	0.063 (12)*
H4E	0.605 (5)	0.598 (6)	0.294 (3)	0.17 (3)*
H5E	0.534 (4)	0.605 (5)	0.330 (2)	0.11 (2)*
H6E	0.557 (4)	0.477 (5)	0.300 (2)	0.14 (2)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0254 (14)	0.0379 (14)	0.0429 (15)	0.0038 (11)	0.0110 (12)	0.0122 (12)
C2A	0.0298 (17)	0.0371 (16)	0.0390 (18)	0.0000 (13)	0.0104 (14)	0.0077 (15)
N2A	0.0288 (18)	0.0572 (18)	0.0516 (19)	0.0032 (14)	0.0151 (15)	0.0237 (15)
N3A	0.0253 (14)	0.0414 (14)	0.0410 (14)	0.0003 (10)	0.0095 (11)	0.0088 (12)
C4A	0.0273 (17)	0.0331 (15)	0.0349 (16)	0.0003 (12)	0.0080 (13)	0.0030 (14)
N4A	0.0255 (15)	0.0426 (16)	0.0407 (16)	0.0016 (12)	0.0110 (13)	0.0102 (14)
C4AA	0.0280 (17)	0.0343 (15)	0.0361 (17)	0.0013 (12)	0.0081 (13)	0.0048 (14)
N5A	0.0274 (14)	0.0350 (13)	0.0370 (14)	0.0031 (10)	0.0104 (11)	0.0038 (12)
C6A	0.0314 (17)	0.0329 (16)	0.0374 (17)	0.0031 (12)	0.0125 (14)	0.0036 (13)
C7A	0.0276 (16)	0.0346 (16)	0.0355 (16)	0.0023 (12)	0.0122 (13)	0.0015 (14)
N7A	0.0252 (16)	0.0493 (17)	0.0475 (17)	0.0072 (13)	0.0116 (13)	0.0189 (14)
N8A	0.0273 (14)	0.0341 (13)	0.0415 (14)	0.0023 (10)	0.0133 (11)	0.0073 (12)
C8AA	0.0317 (17)	0.0318 (15)	0.0381 (17)	0.0016 (12)	0.0113 (14)	0.0012 (14)
C9A	0.0281 (16)	0.0370 (16)	0.0376 (17)	0.0012 (12)	0.0092 (13)	0.0058 (14)
C10A	0.0408 (19)	0.0489 (19)	0.0433 (19)	0.0153 (15)	0.0149 (15)	0.0110 (16)
C11A	0.046 (2)	0.077 (3)	0.043 (2)	0.0130 (18)	0.0188 (17)	0.0163 (19)
C12A	0.042 (2)	0.054 (2)	0.050 (2)	0.0074 (16)	0.0103 (17)	0.0205 (19)
C13A	0.0356 (19)	0.0400 (18)	0.057 (2)	0.0070 (14)	0.0083 (16)	0.0083 (17)
C14A	0.0295 (17)	0.0421 (18)	0.0416 (19)	0.0042 (13)	0.0087 (14)	0.0065 (15)
N1B	0.0235 (14)	0.0355 (14)	0.0326 (14)	−0.0037 (11)	0.0090 (11)	0.0025 (11)
C2B	0.0261 (16)	0.0331 (15)	0.0328 (16)	−0.0008 (12)	0.0072 (13)	−0.0009 (14)
N2B	0.0265 (16)	0.0480 (16)	0.0479 (17)	0.0034 (13)	0.0093 (14)	0.0151 (14)
N3B	0.0258 (13)	0.0319 (13)	0.0347 (13)	0.0011 (10)	0.0089 (11)	0.0034 (11)
C4B	0.0266 (16)	0.0306 (15)	0.0322 (16)	−0.0019 (12)	0.0090 (13)	−0.0038 (13)
N4B	0.0252 (15)	0.0429 (15)	0.0377 (15)	0.0016 (11)	0.0117 (12)	0.0080 (13)
C4AB	0.0271 (16)	0.0289 (15)	0.0273 (15)	−0.0009 (11)	0.0074 (12)	0.0001 (13)
N5B	0.0260 (13)	0.0319 (13)	0.0321 (13)	0.0003 (10)	0.0077 (10)	−0.0004 (11)
C6B	0.0275 (17)	0.0314 (15)	0.0304 (15)	−0.0004 (12)	0.0069 (12)	−0.0017 (13)
C7B	0.0291 (16)	0.0285 (15)	0.0300 (15)	−0.0020 (12)	0.0100 (12)	−0.0032 (13)
N7B	0.0246 (15)	0.0420 (15)	0.0433 (16)	0.0016 (12)	0.0109 (13)	0.0122 (13)
C8AB	0.0263 (16)	0.0261 (14)	0.0287 (15)	−0.0014 (11)	0.0062 (12)	−0.0010 (12)
N8B	0.0239 (13)	0.0324 (13)	0.0323 (13)	0.0004 (10)	0.0101 (10)	−0.0004 (11)
C9B	0.0247 (16)	0.0327 (15)	0.0373 (17)	−0.0032 (12)	0.0059 (13)	0.0037 (13)
C10B	0.0301 (17)	0.0374 (17)	0.0431 (18)	−0.0006 (13)	0.0085 (14)	0.0039 (15)
C11B	0.0265 (17)	0.0367 (18)	0.060 (2)	0.0009 (14)	0.0070 (16)	0.0033 (17)
C12B	0.037 (2)	0.051 (2)	0.069 (3)	0.0009 (16)	0.0072 (18)	0.028 (2)
C13B	0.039 (2)	0.066 (2)	0.048 (2)	0.0023 (17)	0.0153 (17)	0.0195 (18)
C14B	0.0308 (18)	0.0426 (19)	0.0427 (19)	0.0039 (14)	0.0081 (15)	0.0059 (16)
C1C	0.036 (2)	0.057 (2)	0.046 (2)	−0.0024 (15)	0.0149 (16)	0.0047 (17)
O1C	0.0320 (12)	0.0547 (13)	0.0436 (13)	0.0024 (10)	0.0107 (10)	0.0128 (11)
C2C	0.046 (2)	0.087 (3)	0.049 (2)	−0.0183 (19)	0.0108 (18)	0.015 (2)
O2C	0.0313 (14)	0.1009 (19)	0.0473 (14)	−0.0074 (12)	0.0055 (11)	0.0244 (13)
C3C	0.041 (2)	0.052 (2)	0.053 (2)	0.0001 (16)	0.0154 (17)	0.0155 (17)
O3C	0.0363 (13)	0.0520 (13)	0.0588 (15)	−0.0051 (10)	0.0152 (11)	−0.0217 (13)
C4C	0.049 (2)	0.043 (2)	0.100 (3)	0.0020 (18)	0.035 (2)	0.016 (2)
O4C	0.062 (2)	0.149 (3)	0.146 (3)	−0.0565 (19)	0.064 (2)	−0.110 (3)
C5C	0.068 (3)	0.049 (2)	0.120 (4)	−0.016 (2)	0.053 (3)	−0.035 (3)
C6C	0.082 (4)	0.092 (3)	0.081 (3)	−0.026 (3)	0.023 (3)	0.001 (3)
C7C	0.085 (4)	0.096 (4)	0.154 (5)	−0.048 (3)	0.062 (4)	−0.076 (4)
C8C	0.041 (2)	0.059 (2)	0.070 (3)	−0.0153 (17)	0.026 (2)	−0.030 (2)
C9C	0.0342 (19)	0.049 (2)	0.060 (2)	−0.0021 (14)	0.0167 (16)	−0.0164 (18)
C1D	0.080 (4)	0.047 (3)	0.083 (3)	−0.020 (2)	0.019 (3)	−0.003 (3)
O1D	0.0407 (13)	0.0449 (12)	0.0542 (14)	0.0008 (10)	0.0111 (11)	0.0170 (11)
S1D	0.0402 (5)	0.0424 (5)	0.0488 (5)	0.0040 (3)	0.0097 (4)	0.0105 (4)
C2D	0.049 (2)	0.067 (3)	0.050 (2)	0.007 (2)	0.011 (2)	0.006 (2)
C1E	0.164 (6)	0.120 (4)	0.088 (4)	−0.071 (4)	−0.002 (4)	0.030 (3)
O1E	0.0398 (14)	0.0750 (17)	0.0842 (18)	−0.0063 (12)	0.0156 (13)	−0.0426 (15)
S1E	0.0404 (5)	0.0605 (6)	0.0813 (7)	0.0143 (4)	−0.0096 (5)	−0.0287 (5)
C2E	0.096 (4)	0.107 (4)	0.063 (3)	−0.029 (4)	0.006 (3)	0.001 (3)

Geometric parameters (Å, º)

N1A—C8AA	1.362 (4)	C9B—C10B	1.392 (4)
N1A—C2A	1.366 (4)	C9B—C14B	1.394 (4)
N1A—H1XA	0.90 (4)	C10B—C11B	1.385 (4)
C2A—N2A	1.312 (4)	C10B—H10B	0.97 (3)
C2A—N3A	1.351 (4)	C11B—C12B	1.384 (5)
N2A—H2A	0.86 (4)	C11B—H11B	0.85 (3)
N2A—H3A	0.79 (4)	C12B—C13B	1.380 (5)
N3A—C4A	1.335 (4)	C12B—H12B	0.92 (4)
C4A—N4A	1.322 (4)	C13B—C14B	1.383 (5)
C4A—C4AA	1.426 (4)	C13B—H13B	1.05 (4)
N4A—H4A	0.85 (3)	C14B—H14B	0.89 (3)
N4A—H5A	0.81 (3)	C1C—O2C	1.247 (4)
C4AA—N5A	1.356 (4)	C1C—O1C	1.267 (4)
C4AA—C8AA	1.396 (4)	C1C—C2C	1.519 (5)
N5A—C6A	1.312 (4)	C2C—C3C	1.535 (5)
C6A—C7A	1.454 (4)	C2C—H2C	0.9900
C6A—C9A	1.486 (4)	C2C—H3C	0.9900
C7A—N7A	1.331 (4)	C3C—C4C	1.500 (5)
C7A—N8A	1.337 (4)	C3C—H4C	1.02 (3)
N7A—H6A	0.90 (3)	C3C—H5C	1.06 (4)
N7A—H7A	0.78 (4)	O3C—C9C	1.251 (4)
N8A—C8AA	1.349 (4)	C4C—C5C	1.492 (6)
C9A—C14A	1.393 (4)	C4C—H6C	1.01 (4)
C9A—C10A	1.395 (4)	C4C—H7C	1.03 (4)
C10A—C11A	1.392 (5)	O4C—C9C	1.240 (4)
C10A—H10A	0.99 (3)	C5C—C6C	1.601 (7)
C11A—C12A	1.366 (5)	C5C—H8C	1.01 (3)
C11A—H11A	0.93 (4)	C5C—H9C	1.02 (4)
C12A—C13A	1.387 (5)	C6C—C7C	1.379 (7)
C12A—H12A	0.95 (3)	C6C—H10C	1.08 (4)
C13A—C14A	1.391 (4)	C6C—H11C	1.20 (5)
C13A—H13A	1.03 (3)	C7C—C8C	1.535 (6)
C14A—H14A	1.01 (3)	C7C—H12C	0.9900
N1B—C2B	1.354 (4)	C7C—H13C	0.9900
N1B—C8AB	1.370 (4)	C8C—C9C	1.505 (5)
N1B—H1XB	0.82 (4)	C8C—H14C	0.91 (4)
C2B—N2B	1.321 (4)	C8C—H15C	1.16 (5)
C2B—N3B	1.340 (4)	C1D—S1D	1.794 (4)
N2B—H2B	0.90 (4)	C1D—H1D	1.03 (7)
N2B—H3B	0.85 (3)	C1D—H2D	0.77 (5)
N3B—C4B	1.344 (4)	C1D—H3D	1.00 (4)
C4B—N4B	1.329 (4)	O1D—S1D	1.503 (2)
C4B—C4AB	1.434 (4)	S1D—C2D	1.779 (4)
N4B—H4B	0.97 (4)	C2D—H4D	1.04 (4)
N4B—H5B	0.88 (4)	C2D—H5D	0.91 (4)
C4AB—N5B	1.356 (3)	C2D—H6D	0.94 (4)
C4AB—C8AB	1.396 (4)	C1E—S1E	1.780 (6)
N5B—C6B	1.313 (3)	C1E—H1E	0.9800
C6B—C7B	1.449 (4)	C1E—H2E	0.9800
C6B—C9B	1.488 (4)	C1E—H3E	0.9800
C7B—N7B	1.326 (4)	O1E—S1E	1.489 (2)
C7B—N8B	1.350 (3)	S1E—C2E	1.750 (5)
N7B—H6B	0.85 (4)	C2E—H4E	0.93 (8)
N7B—H7B	0.88 (3)	C2E—H5E	0.96 (5)
C8AB—N8B	1.339 (3)	C2E—H6E	1.10 (6)
C8AA—N1A—C2A	120.1 (3)	C12B—C11B—C10B	120.2 (3)
C8AA—N1A—H1XA	124 (2)	C12B—C11B—H11B	124 (2)
C2A—N1A—H1XA	115 (2)	C10B—C11B—H11B	116 (2)
N2A—C2A—N3A	119.5 (3)	C13B—C12B—C11B	119.8 (3)
N2A—C2A—N1A	117.5 (3)	C13B—C12B—H12B	121 (2)
N3A—C2A—N1A	123.0 (3)	C11B—C12B—H12B	119 (2)
C2A—N2A—H2A	122 (3)	C12B—C13B—C14B	120.4 (3)
C2A—N2A—H3A	116 (3)	C12B—C13B—H13B	119 (2)
H2A—N2A—H3A	122 (4)	C14B—C13B—H13B	120 (2)
C4A—N3A—C2A	118.5 (2)	C13B—C14B—C9B	120.2 (3)
N4A—C4A—N3A	118.5 (3)	C13B—C14B—H14B	122.9 (17)
N4A—C4A—C4AA	120.4 (3)	C9B—C14B—H14B	116.9 (17)
N3A—C4A—C4AA	121.1 (3)	O2C—C1C—O1C	124.6 (3)
C4A—N4A—H4A	116.8 (19)	O2C—C1C—C2C	117.6 (3)
C4A—N4A—H5A	116 (2)	O1C—C1C—C2C	117.7 (3)
H4A—N4A—H5A	127 (3)	C1C—C2C—C3C	114.3 (3)
N5A—C4AA—C8AA	120.9 (3)	C1C—C2C—H2C	108.7
N5A—C4AA—C4A	120.5 (2)	C3C—C2C—H2C	108.7
C8AA—C4AA—C4A	118.6 (3)	C1C—C2C—H3C	108.7
C6A—N5A—C4AA	118.6 (2)	C3C—C2C—H3C	108.7
N5A—C6A—C7A	119.9 (3)	H2C—C2C—H3C	107.6
N5A—C6A—C9A	117.1 (2)	C4C—C3C—C2C	111.7 (3)
C7A—C6A—C9A	122.9 (3)	C4C—C3C—H4C	112.9 (16)
N7A—C7A—N8A	117.7 (3)	C2C—C3C—H4C	103.6 (17)
N7A—C7A—C6A	120.5 (3)	C4C—C3C—H5C	111.1 (19)
N8A—C7A—C6A	121.8 (3)	C2C—C3C—H5C	108.8 (18)
C7A—N7A—H6A	120 (2)	H4C—C3C—H5C	109 (2)
C7A—N7A—H7A	122 (2)	C5C—C4C—C3C	114.6 (3)
H6A—N7A—H7A	118 (3)	C5C—C4C—H6C	104 (2)
C7A—N8A—C8AA	116.2 (2)	C3C—C4C—H6C	113 (2)
N8A—C8AA—N1A	118.9 (3)	C5C—C4C—H7C	102.2 (19)
N8A—C8AA—C4AA	122.4 (3)	C3C—C4C—H7C	112.1 (19)
N1A—C8AA—C4AA	118.7 (3)	H6C—C4C—H7C	110 (3)
C14A—C9A—C10A	119.5 (3)	C4C—C5C—C6C	105.8 (4)
C14A—C9A—C6A	118.0 (3)	C4C—C5C—H8C	112.8 (18)
C10A—C9A—C6A	122.5 (3)	C6C—C5C—H8C	116.8 (17)
C11A—C10A—C9A	119.4 (3)	C4C—C5C—H9C	108.2 (19)
C11A—C10A—H10A	116.0 (19)	C6C—C5C—H9C	110 (2)
C9A—C10A—H10A	124.5 (19)	H8C—C5C—H9C	103 (3)
C12A—C11A—C10A	120.8 (3)	C7C—C6C—C5C	113.4 (5)
C12A—C11A—H11A	122 (2)	C7C—C6C—H10C	105 (2)
C10A—C11A—H11A	117 (2)	C5C—C6C—H10C	111 (2)
C11A—C12A—C13A	120.4 (3)	C7C—C6C—H11C	107 (2)
C11A—C12A—H12A	118 (2)	C5C—C6C—H11C	109 (2)
C13A—C12A—H12A	121 (2)	H10C—C6C—H11C	112 (3)
C12A—C13A—C14A	119.6 (3)	C6C—C7C—C8C	118.3 (5)
C12A—C13A—H13A	118.7 (19)	C6C—C7C—H12C	107.7
C14A—C13A—H13A	121.7 (19)	C8C—C7C—H12C	107.7
C13A—C14A—C9A	120.2 (3)	C6C—C7C—H13C	107.7
C13A—C14A—H14A	120.9 (16)	C8C—C7C—H13C	107.7
C9A—C14A—H14A	118.8 (16)	H12C—C7C—H13C	107.1
C2B—N1B—C8AB	119.8 (3)	C9C—C8C—C7C	115.0 (3)
C2B—N1B—H1XB	116 (2)	C9C—C8C—H14C	111 (3)
C8AB—N1B—H1XB	124 (2)	C7C—C8C—H14C	112 (3)
N2B—C2B—N3B	119.0 (3)	C9C—C8C—H15C	105 (2)
N2B—C2B—N1B	116.9 (3)	C7C—C8C—H15C	113 (2)
N3B—C2B—N1B	124.1 (3)	H14C—C8C—H15C	100 (3)
C2B—N2B—H2B	121 (2)	O4C—C9C—O3C	122.7 (3)
C2B—N2B—H3B	122 (2)	O4C—C9C—C8C	118.3 (3)
H2B—N2B—H3B	117 (3)	O3C—C9C—C8C	118.9 (3)
C2B—N3B—C4B	117.9 (2)	S1D—C1D—H1D	110 (3)
N4B—C4B—N3B	117.9 (3)	S1D—C1D—H2D	114 (4)
N4B—C4B—C4AB	121.1 (3)	H1D—C1D—H2D	98 (5)
N3B—C4B—C4AB	121.0 (2)	S1D—C1D—H3D	110 (2)
C4B—N4B—H4B	121.5 (18)	H1D—C1D—H3D	105 (4)
C4B—N4B—H5B	124 (2)	H2D—C1D—H3D	118 (5)
H4B—N4B—H5B	115 (3)	O1D—S1D—C2D	106.38 (18)
N5B—C4AB—C8AB	120.8 (2)	O1D—S1D—C1D	105.8 (2)
N5B—C4AB—C4B	120.9 (2)	C2D—S1D—C1D	96.6 (2)
C8AB—C4AB—C4B	118.2 (2)	S1D—C2D—H4D	109.8 (18)
C6B—N5B—C4AB	118.2 (2)	S1D—C2D—H5D	108 (3)
N5B—C6B—C7B	120.6 (2)	H4D—C2D—H5D	117 (3)
N5B—C6B—C9B	117.3 (2)	S1D—C2D—H6D	107 (2)
C7B—C6B—C9B	122.1 (2)	H4D—C2D—H6D	106 (3)
N7B—C7B—N8B	117.6 (3)	H5D—C2D—H6D	109 (3)
N7B—C7B—C6B	121.6 (3)	S1E—C1E—H1E	109.5
N8B—C7B—C6B	120.8 (2)	S1E—C1E—H2E	109.5
C7B—N7B—H6B	124 (2)	H1E—C1E—H2E	109.5
C7B—N7B—H7B	120 (2)	S1E—C1E—H3E	109.5
H6B—N7B—H7B	116 (3)	H1E—C1E—H3E	109.5
N8B—C8AB—N1B	118.9 (2)	H2E—C1E—H3E	109.5
N8B—C8AB—C4AB	122.5 (2)	O1E—S1E—C2E	107.4 (3)
N1B—C8AB—C4AB	118.6 (2)	O1E—S1E—C1E	106.9 (2)
C8AB—N8B—C7B	116.6 (2)	C2E—S1E—C1E	94.8 (3)
C10B—C9B—C14B	119.1 (3)	S1E—C2E—H4E	123 (5)
C10B—C9B—C6B	121.3 (3)	S1E—C2E—H5E	104 (3)
C14B—C9B—C6B	119.4 (3)	H4E—C2E—H5E	109 (5)
C11B—C10B—C9B	120.2 (3)	S1E—C2E—H6E	108 (3)
C11B—C10B—H10B	121.7 (17)	H4E—C2E—H6E	101 (5)
C9B—C10B—H10B	118.1 (16)	H5E—C2E—H6E	112 (5)
C8AA—N1A—C2A—N2A	−179.3 (3)	C2B—N3B—C4B—C4AB	1.7 (4)
C8AA—N1A—C2A—N3A	0.9 (4)	N4B—C4B—C4AB—N5B	−6.7 (4)
N2A—C2A—N3A—C4A	179.3 (3)	N3B—C4B—C4AB—N5B	171.9 (2)
N1A—C2A—N3A—C4A	−0.9 (4)	N4B—C4B—C4AB—C8AB	176.9 (2)
C2A—N3A—C4A—N4A	179.7 (3)	N3B—C4B—C4AB—C8AB	−4.5 (4)
C2A—N3A—C4A—C4AA	0.3 (4)	C8AB—C4AB—N5B—C6B	−2.2 (4)
N4A—C4A—C4AA—N5A	3.2 (4)	C4B—C4AB—N5B—C6B	−178.5 (2)
N3A—C4A—C4AA—N5A	−177.4 (3)	C4AB—N5B—C6B—C7B	−4.3 (4)
N4A—C4A—C4AA—C8AA	−179.0 (3)	C4AB—N5B—C6B—C9B	175.0 (2)
N3A—C4A—C4AA—C8AA	0.4 (4)	N5B—C6B—C7B—N7B	−171.8 (3)
C8AA—C4AA—N5A—C6A	2.6 (4)	C9B—C6B—C7B—N7B	9.0 (4)
C4A—C4AA—N5A—C6A	−179.7 (3)	N5B—C6B—C7B—N8B	7.0 (4)
C4AA—N5A—C6A—C7A	1.7 (4)	C9B—C6B—C7B—N8B	−172.2 (2)
C4AA—N5A—C6A—C9A	179.0 (2)	C2B—N1B—C8AB—N8B	−178.3 (2)
N5A—C6A—C7A—N7A	173.7 (3)	C2B—N1B—C8AB—C4AB	2.5 (4)
C9A—C6A—C7A—N7A	−3.4 (4)	N5B—C4AB—C8AB—N8B	6.8 (4)
N5A—C6A—C7A—N8A	−5.0 (4)	C4B—C4AB—C8AB—N8B	−176.8 (2)
C9A—C6A—C7A—N8A	177.9 (3)	N5B—C4AB—C8AB—N1B	−174.1 (2)
N7A—C7A—N8A—C8AA	−175.3 (3)	C4B—C4AB—C8AB—N1B	2.3 (4)
C6A—C7A—N8A—C8AA	3.4 (4)	N1B—C8AB—N8B—C7B	176.8 (2)
C7A—N8A—C8AA—N1A	179.4 (2)	C4AB—C8AB—N8B—C7B	−4.0 (4)
C7A—N8A—C8AA—C4AA	1.0 (4)	N7B—C7B—N8B—C8AB	176.3 (2)
C2A—N1A—C8AA—N8A	−178.7 (3)	C6B—C7B—N8B—C8AB	−2.6 (4)
C2A—N1A—C8AA—C4AA	−0.2 (4)	N5B—C6B—C9B—C10B	−134.6 (3)
N5A—C4AA—C8AA—N8A	−4.2 (4)	C7B—C6B—C9B—C10B	44.7 (4)
C4A—C4AA—C8AA—N8A	178.0 (3)	N5B—C6B—C9B—C14B	40.1 (4)
N5A—C4AA—C8AA—N1A	177.4 (2)	C7B—C6B—C9B—C14B	−140.6 (3)
C4A—C4AA—C8AA—N1A	−0.5 (4)	C14B—C9B—C10B—C11B	0.5 (4)
N5A—C6A—C9A—C14A	−43.4 (4)	C6B—C9B—C10B—C11B	175.2 (3)
C7A—C6A—C9A—C14A	133.8 (3)	C9B—C10B—C11B—C12B	0.1 (5)
N5A—C6A—C9A—C10A	135.1 (3)	C10B—C11B—C12B—C13B	−0.1 (5)
C7A—C6A—C9A—C10A	−47.8 (4)	C11B—C12B—C13B—C14B	−0.6 (5)
C14A—C9A—C10A—C11A	−1.4 (5)	C12B—C13B—C14B—C9B	1.3 (5)
C6A—C9A—C10A—C11A	−179.8 (3)	C10B—C9B—C14B—C13B	−1.2 (5)
C9A—C10A—C11A—C12A	0.3 (5)	C6B—C9B—C14B—C13B	−176.0 (3)
C10A—C11A—C12A—C13A	0.4 (6)	O2C—C1C—C2C—C3C	43.7 (5)
C11A—C12A—C13A—C14A	0.0 (5)	O1C—C1C—C2C—C3C	−139.6 (3)
C12A—C13A—C14A—C9A	−1.0 (5)	C1C—C2C—C3C—C4C	66.8 (4)
C10A—C9A—C14A—C13A	1.7 (5)	C2C—C3C—C4C—C5C	168.9 (4)
C6A—C9A—C14A—C13A	−179.7 (3)	C3C—C4C—C5C—C6C	−175.7 (4)
C8AB—N1B—C2B—N2B	174.2 (2)	C4C—C5C—C6C—C7C	−177.7 (4)
C8AB—N1B—C2B—N3B	−5.8 (4)	C5C—C6C—C7C—C8C	163.3 (4)
N2B—C2B—N3B—C4B	−176.5 (2)	C6C—C7C—C8C—C9C	−73.9 (6)
N1B—C2B—N3B—C4B	3.6 (4)	C7C—C8C—C9C—O4C	34.6 (6)
C2B—N3B—C4B—N4B	−179.7 (2)	C7C—C8C—C9C—O3C	−147.4 (4)

Triamterenium nicotinate, Triamterene and DMSO solvate (1f_DMSO)

Crystal data

C12H12N7^+·C12H11N7·C6H4NO2^−·2(C2H6OS)	F(000) = 1648
Mr = 785.92	Dx = 1.391 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.7107 Å
a = 14.8461 (2) Å	Cell parameters from 12872 reflections
b = 12.3081 (3) Å	θ = 1.0–27.5°
c = 21.2850 (5) Å	µ = 0.20 mm^−1
β = 105.176 (1)°	T = 180 K
V = 3753.71 (14) Å^3	Needle, colourless
Z = 4	0.35 × 0.07 × 0.05 mm

Data collection

Nonius Kappa CCD diffractometer	8467 independent reflections
Radiation source: fine-focus sealed tube	4823 reflections with I > 2σ(I)
None monochromator	Rint = 0.048
Thin slice ω and φ scans	θmax = 27.5°, θmin = 3.6°
Absorption correction: multi-scan multi-scan from symmetry-related measurements Sortav (Blessing 1995)	h = −18→18
Tmin = 0.878, Tmax = 0.998	k = −15→15
23512 measured reflections	l = −23→27

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.041	Hydrogen site location: difference Fourier map
wR(F^2) = 0.089	All H-atom parameters refined
S = 0.90	w = 1/[σ^2(Fo^2) + (0.0421P)^2] where P = (Fo^2 + 2Fc^2)/3
8467 reflections	(Δ/σ)max = 0.001
652 parameters	Δρmax = 0.25 e Å^−3
0 restraints	Δρmin = −0.38 e Å^−3

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
N1A	0.50349 (9)	0.97687 (12)	−0.09678 (7)	0.0247 (3)
C2A	0.41465 (11)	1.01475 (15)	−0.11949 (8)	0.0251 (4)
N2A	0.40045 (12)	1.09028 (14)	−0.16462 (8)	0.0338 (4)
N3A	0.34284 (9)	0.97948 (12)	−0.09733 (7)	0.0258 (3)
C4A	0.35902 (11)	0.90257 (15)	−0.05166 (8)	0.0264 (4)
N4A	0.29044 (11)	0.86944 (15)	−0.02724 (9)	0.0349 (4)
C4AA	0.44969 (10)	0.85334 (14)	−0.02924 (8)	0.0235 (4)
N5A	0.46282 (9)	0.76746 (12)	0.01158 (7)	0.0265 (3)
C6A	0.54657 (11)	0.72222 (15)	0.02947 (8)	0.0254 (4)
C7A	0.62309 (10)	0.77077 (15)	0.00823 (8)	0.0253 (4)
N7A	0.71046 (10)	0.73422 (15)	0.02993 (8)	0.0336 (4)
N8A	0.60930 (9)	0.85484 (12)	−0.03334 (7)	0.0259 (3)
C8AA	0.52169 (11)	0.89398 (14)	−0.05286 (8)	0.0234 (4)
C9A	0.55417 (11)	0.62417 (15)	0.07036 (8)	0.0269 (4)
C10A	0.60248 (11)	0.53138 (15)	0.06050 (9)	0.0308 (4)
C11A	0.60030 (13)	0.43801 (18)	0.09633 (10)	0.0378 (5)
C12A	0.54991 (13)	0.4353 (2)	0.14244 (11)	0.0464 (6)
C13A	0.50157 (14)	0.52630 (18)	0.15238 (11)	0.0461 (6)
C14A	0.50341 (12)	0.61933 (18)	0.11719 (10)	0.0365 (5)
N1B	0.54573 (8)	0.67340 (11)	0.48290 (7)	0.0248 (3)
C2B	0.47207 (11)	0.71323 (14)	0.50096 (8)	0.0243 (4)
N2B	0.48694 (12)	0.79830 (13)	0.54194 (8)	0.0308 (4)
N3B	0.38149 (9)	0.67861 (11)	0.48130 (7)	0.0259 (3)
C4B	0.36431 (10)	0.59581 (14)	0.43962 (8)	0.0239 (4)
N4B	0.27735 (10)	0.55648 (15)	0.42071 (8)	0.0322 (4)
C4AB	0.43605 (10)	0.54897 (14)	0.41463 (8)	0.0221 (4)
N5B	0.41666 (8)	0.46844 (12)	0.36999 (7)	0.0245 (3)
C6B	0.48556 (10)	0.42646 (14)	0.34926 (8)	0.0237 (4)
C7B	0.57981 (11)	0.46831 (15)	0.37552 (8)	0.0262 (4)
N7B	0.65092 (11)	0.42923 (15)	0.35457 (9)	0.0366 (4)
N8B	0.59877 (8)	0.54823 (12)	0.41902 (7)	0.0251 (3)
C8AB	0.52656 (11)	0.59078 (14)	0.43988 (8)	0.0230 (4)
C9B	0.46308 (11)	0.34259 (14)	0.29729 (8)	0.0246 (4)
C10B	0.38469 (12)	0.35676 (17)	0.24519 (9)	0.0298 (4)
C11B	0.36085 (13)	0.28155 (17)	0.19574 (10)	0.0358 (5)
C12B	0.41309 (13)	0.18934 (18)	0.19744 (10)	0.0373 (5)
C13B	0.49067 (13)	0.17225 (17)	0.24905 (10)	0.0339 (5)
C14B	0.51598 (12)	0.24872 (15)	0.29855 (9)	0.0283 (4)
C1C	0.11345 (12)	0.34819 (16)	0.31962 (10)	0.0310 (4)
N1C	0.32325 (9)	0.16232 (13)	0.35956 (7)	0.0345 (4)
O1C	0.13421 (8)	0.40303 (11)	0.37145 (6)	0.0385 (3)
C2C	0.18117 (11)	0.26128 (15)	0.31212 (8)	0.0274 (4)
O2C	0.04021 (8)	0.35890 (12)	0.27467 (6)	0.0430 (4)
C3C	0.16455 (12)	0.19592 (16)	0.25733 (9)	0.0325 (5)
C4C	0.22744 (13)	0.11582 (17)	0.25385 (11)	0.0362 (5)
C5C	0.30433 (13)	0.10133 (17)	0.30589 (10)	0.0364 (5)
C6C	0.26183 (12)	0.24197 (16)	0.36115 (10)	0.0315 (5)
C1D	0.3279 (2)	0.0730 (4)	0.50649 (14)	0.0749 (10)
O1D	0.34563 (8)	−0.07683 (10)	0.59712 (6)	0.0361 (3)
S1D	0.35120 (3)	0.04385 (4)	0.59078 (2)	0.03692 (14)
C2D	0.47179 (15)	0.0791 (2)	0.61244 (14)	0.0482 (6)
C1E	0.75030 (17)	0.0960 (2)	0.27410 (12)	0.0424 (5)
O1E	0.72885 (8)	0.30753 (10)	0.26855 (6)	0.0417 (4)
S1E	0.72396 (3)	0.21220 (4)	0.22365 (2)	0.03268 (13)
C2E	0.82962 (18)	0.2158 (2)	0.19862 (14)	0.0479 (6)
H1XA	0.5484 (14)	1.0172 (17)	−0.1121 (10)	0.058 (6)*
H2A	0.4464 (13)	1.1079 (15)	−0.1839 (9)	0.044 (6)*
H3A	0.3482 (12)	1.1185 (14)	−0.1798 (8)	0.025 (5)*
H4A	0.2324 (14)	0.9000 (15)	−0.0404 (9)	0.041 (6)*
H5A	0.3032 (12)	0.8271 (16)	0.0044 (10)	0.036 (6)*
H6A	0.7228 (11)	0.6777 (15)	0.0569 (9)	0.029 (5)*
H7A	0.7548 (13)	0.7650 (17)	0.0161 (9)	0.047 (6)*
H10A	0.6336 (11)	0.5303 (13)	0.0244 (8)	0.029 (5)*
H11A	0.6325 (12)	0.3762 (16)	0.0889 (9)	0.040 (5)*
H12A	0.5477 (13)	0.3710 (18)	0.1645 (10)	0.051 (6)*
H13A	0.4674 (15)	0.5227 (17)	0.1852 (11)	0.064 (7)*
H14A	0.4692 (11)	0.6839 (14)	0.1224 (8)	0.026 (5)*
H2B	0.5464 (14)	0.8130 (16)	0.5671 (10)	0.048 (6)*
H3B	0.4411 (13)	0.8219 (15)	0.5593 (9)	0.041 (6)*
H4B	0.2336 (13)	0.5860 (15)	0.4394 (9)	0.041 (5)*
H5B	0.2676 (11)	0.4969 (15)	0.3970 (9)	0.028 (5)*
H6B	0.6428 (11)	0.3876 (15)	0.3250 (9)	0.024 (6)*
H7B	0.7043 (13)	0.4580 (15)	0.3703 (9)	0.031 (5)*
H10B	0.3500 (11)	0.4188 (15)	0.2447 (8)	0.028 (5)*
H11B	0.3083 (12)	0.2926 (15)	0.1619 (9)	0.040 (5)*
H12B	0.3969 (11)	0.1331 (16)	0.1650 (9)	0.035 (5)*
H13B	0.5266 (11)	0.1058 (15)	0.2529 (8)	0.033 (5)*
H14B	0.5694 (11)	0.2343 (14)	0.3361 (8)	0.029 (5)*
H3C	0.1096 (12)	0.2099 (14)	0.2235 (8)	0.028 (5)*
H4C	0.2189 (11)	0.0739 (15)	0.2199 (9)	0.034 (5)*
H5C	0.3460 (12)	0.0455 (15)	0.3048 (8)	0.033 (5)*
H6C	0.2814 (10)	0.2873 (14)	0.4004 (8)	0.029 (5)*
H1D	0.2649 (19)	0.061 (2)	0.4886 (12)	0.081 (8)*
H2D	0.3672 (19)	0.022 (2)	0.4877 (13)	0.092 (10)*
H3D	0.3356 (17)	0.149 (2)	0.5031 (12)	0.083 (10)*
H4D	0.4949 (16)	0.062 (2)	0.6572 (14)	0.086 (9)*
H5D	0.4759 (15)	0.155 (2)	0.6015 (11)	0.069 (8)*
H6D	0.5042 (15)	0.0331 (19)	0.5894 (11)	0.061 (7)*
H1E	0.7036 (15)	0.0889 (18)	0.2950 (11)	0.068 (7)*
H2E	0.8067 (14)	0.1109 (15)	0.3049 (10)	0.044 (6)*
H3E	0.7542 (13)	0.0323 (18)	0.2503 (10)	0.052 (7)*
H4E	0.8795 (15)	0.2191 (17)	0.2379 (11)	0.058 (7)*
H5E	0.8252 (15)	0.280 (2)	0.1736 (11)	0.068 (8)*
H6E	0.8314 (13)	0.1531 (19)	0.1727 (10)	0.055 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0200 (8)	0.0273 (9)	0.0273 (9)	0.0012 (6)	0.0070 (6)	0.0043 (7)
C2A	0.0239 (9)	0.0260 (11)	0.0247 (10)	0.0002 (8)	0.0047 (7)	−0.0022 (9)
N2A	0.0209 (9)	0.0397 (11)	0.0407 (11)	0.0047 (8)	0.0081 (8)	0.0137 (9)
N3A	0.0224 (7)	0.0284 (9)	0.0275 (9)	0.0013 (6)	0.0079 (6)	0.0014 (7)
C4A	0.0233 (9)	0.0302 (11)	0.0265 (11)	−0.0002 (8)	0.0079 (7)	−0.0040 (9)
N4A	0.0236 (9)	0.0452 (12)	0.0377 (11)	0.0084 (8)	0.0111 (8)	0.0168 (9)
C4AA	0.0217 (9)	0.0246 (11)	0.0246 (10)	0.0003 (7)	0.0070 (7)	−0.0013 (9)
N5A	0.0241 (8)	0.0290 (10)	0.0267 (9)	0.0011 (6)	0.0068 (6)	−0.0006 (7)
C6A	0.0234 (9)	0.0281 (11)	0.0247 (10)	0.0017 (8)	0.0061 (7)	−0.0018 (9)
C7A	0.0210 (9)	0.0291 (11)	0.0265 (10)	0.0022 (8)	0.0072 (7)	−0.0014 (9)
N7A	0.0209 (9)	0.0362 (11)	0.0447 (11)	0.0040 (7)	0.0102 (7)	0.0170 (9)
N8A	0.0201 (7)	0.0296 (9)	0.0281 (9)	0.0039 (6)	0.0067 (6)	0.0019 (8)
C8AA	0.0239 (9)	0.0234 (11)	0.0231 (10)	−0.0005 (7)	0.0065 (7)	−0.0029 (9)
C9A	0.0206 (8)	0.0276 (11)	0.0315 (11)	−0.0003 (7)	0.0052 (7)	0.0017 (9)
C10A	0.0233 (9)	0.0322 (12)	0.0349 (12)	−0.0003 (8)	0.0043 (8)	0.0009 (10)
C11A	0.0297 (10)	0.0290 (13)	0.0495 (14)	0.0021 (9)	0.0009 (9)	0.0016 (11)
C12A	0.0379 (12)	0.0391 (15)	0.0608 (16)	−0.0053 (10)	0.0104 (10)	0.0198 (13)
C13A	0.0427 (12)	0.0459 (15)	0.0559 (15)	0.0028 (11)	0.0241 (11)	0.0166 (12)
C14A	0.0326 (11)	0.0362 (13)	0.0438 (13)	0.0063 (9)	0.0156 (9)	0.0092 (11)
N1B	0.0219 (7)	0.0249 (9)	0.0282 (9)	−0.0002 (6)	0.0077 (6)	−0.0027 (7)
C2B	0.0243 (9)	0.0251 (11)	0.0238 (10)	−0.0007 (8)	0.0067 (7)	0.0024 (9)
N2B	0.0239 (9)	0.0338 (10)	0.0357 (10)	−0.0006 (7)	0.0094 (8)	−0.0117 (8)
N3B	0.0214 (7)	0.0266 (9)	0.0308 (9)	−0.0029 (6)	0.0088 (6)	−0.0037 (7)
C4B	0.0188 (9)	0.0258 (11)	0.0274 (10)	−0.0005 (7)	0.0068 (7)	0.0019 (9)
N4B	0.0224 (9)	0.0358 (11)	0.0408 (10)	−0.0038 (7)	0.0127 (7)	−0.0140 (9)
C4AB	0.0219 (9)	0.0236 (10)	0.0209 (10)	−0.0009 (7)	0.0058 (7)	0.0014 (8)
N5B	0.0215 (7)	0.0260 (9)	0.0269 (9)	0.0014 (6)	0.0080 (6)	0.0006 (7)
C6B	0.0233 (9)	0.0239 (11)	0.0240 (10)	0.0008 (7)	0.0061 (7)	0.0020 (8)
C7B	0.0208 (9)	0.0301 (11)	0.0290 (11)	−0.0016 (8)	0.0093 (7)	0.0001 (9)
N7B	0.0215 (9)	0.0452 (12)	0.0455 (12)	−0.0071 (8)	0.0133 (8)	−0.0230 (10)
N8B	0.0215 (7)	0.0260 (9)	0.0291 (9)	−0.0020 (6)	0.0088 (6)	−0.0041 (7)
C8AB	0.0216 (9)	0.0246 (11)	0.0242 (10)	0.0009 (7)	0.0084 (7)	0.0042 (9)
C9B	0.0232 (9)	0.0250 (11)	0.0276 (10)	−0.0047 (8)	0.0102 (8)	−0.0017 (9)
C10B	0.0277 (10)	0.0308 (12)	0.0319 (12)	0.0005 (9)	0.0094 (8)	−0.0019 (10)
C11B	0.0285 (10)	0.0465 (14)	0.0313 (12)	−0.0058 (10)	0.0062 (9)	−0.0046 (11)
C12B	0.0357 (11)	0.0410 (14)	0.0391 (13)	−0.0097 (10)	0.0166 (10)	−0.0153 (11)
C13B	0.0307 (10)	0.0293 (12)	0.0462 (13)	−0.0015 (9)	0.0183 (9)	−0.0066 (10)
C14B	0.0245 (9)	0.0286 (11)	0.0336 (12)	−0.0023 (8)	0.0109 (8)	−0.0022 (9)
C1C	0.0248 (10)	0.0338 (12)	0.0363 (12)	−0.0036 (8)	0.0113 (9)	−0.0006 (10)
N1C	0.0309 (8)	0.0371 (10)	0.0357 (10)	0.0005 (7)	0.0092 (7)	−0.0031 (8)
O1C	0.0266 (7)	0.0426 (9)	0.0454 (9)	−0.0015 (6)	0.0077 (6)	−0.0177 (7)
C2C	0.0242 (9)	0.0305 (11)	0.0298 (11)	−0.0043 (8)	0.0114 (8)	−0.0014 (9)
O2C	0.0316 (7)	0.0605 (10)	0.0352 (8)	0.0108 (6)	0.0055 (6)	−0.0030 (7)
C3C	0.0255 (10)	0.0411 (13)	0.0305 (12)	−0.0039 (9)	0.0066 (9)	−0.0018 (10)
C4C	0.0400 (12)	0.0368 (13)	0.0347 (13)	−0.0075 (10)	0.0148 (10)	−0.0110 (11)
C5C	0.0331 (11)	0.0315 (13)	0.0477 (14)	0.0017 (9)	0.0160 (10)	−0.0013 (11)
C6C	0.0292 (10)	0.0358 (13)	0.0311 (12)	−0.0041 (9)	0.0109 (8)	−0.0042 (10)
C1D	0.0506 (17)	0.105 (3)	0.0602 (19)	−0.0246 (18)	−0.0018 (14)	0.0338 (19)
O1D	0.0345 (7)	0.0304 (8)	0.0452 (8)	−0.0037 (6)	0.0136 (6)	−0.0015 (7)
S1D	0.0364 (3)	0.0339 (3)	0.0439 (3)	−0.0003 (2)	0.0165 (2)	0.0015 (3)
C2D	0.0450 (13)	0.0483 (18)	0.0496 (17)	−0.0121 (12)	0.0096 (12)	0.0013 (14)
C1E	0.0400 (13)	0.0455 (16)	0.0427 (14)	−0.0034 (11)	0.0122 (12)	0.0006 (12)
O1E	0.0313 (7)	0.0418 (9)	0.0536 (9)	−0.0039 (6)	0.0138 (6)	−0.0203 (7)
S1E	0.0321 (3)	0.0331 (3)	0.0321 (3)	0.0001 (2)	0.0071 (2)	−0.0054 (2)
C2E	0.0579 (15)	0.0424 (16)	0.0543 (17)	−0.0016 (12)	0.0342 (14)	−0.0041 (15)

Geometric parameters (Å, º)

N1A—C8AA	1.362 (2)	C6B—C9B	1.486 (2)
N1A—C2A	1.363 (2)	C7B—N8B	1.329 (2)
N1A—H1XA	0.95 (2)	C7B—N7B	1.338 (2)
C2A—N2A	1.314 (2)	N7B—H6B	0.796 (18)
C2A—N3A	1.346 (2)	N7B—H7B	0.853 (18)
N2A—H2A	0.91 (2)	N8B—C8AB	1.367 (2)
N2A—H3A	0.834 (17)	C9B—C10B	1.392 (2)
N3A—C4A	1.333 (2)	C9B—C14B	1.393 (2)
C4A—N4A	1.323 (2)	C10B—C11B	1.377 (3)
C4A—C4AA	1.439 (2)	C10B—H10B	0.919 (18)
N4A—H4A	0.91 (2)	C11B—C12B	1.370 (3)
N4A—H5A	0.83 (2)	C11B—H11B	0.923 (18)
C4AA—N5A	1.350 (2)	C12B—C13B	1.384 (3)
C4AA—C8AA	1.388 (2)	C12B—H12B	0.963 (19)
N5A—C6A	1.324 (2)	C13B—C14B	1.389 (3)
C6A—C7A	1.456 (2)	C13B—H13B	0.968 (18)
C6A—C9A	1.475 (2)	C14B—H14B	0.983 (17)
C7A—N7A	1.336 (2)	C1C—O2C	1.253 (2)
C7A—N8A	1.342 (2)	C1C—O1C	1.261 (2)
N7A—H6A	0.890 (19)	C1C—C2C	1.505 (2)
N7A—H7A	0.88 (2)	N1C—C5C	1.334 (2)
N8A—C8AA	1.347 (2)	N1C—C6C	1.345 (2)
C9A—C10A	1.394 (2)	C2C—C3C	1.385 (2)
C9A—C14A	1.399 (2)	C2C—C6C	1.388 (2)
C10A—C11A	1.384 (3)	C3C—C4C	1.373 (3)
C10A—H10A	0.996 (17)	C3C—H3C	0.952 (17)
C11A—C12A	1.381 (3)	C4C—C5C	1.378 (3)
C11A—H11A	0.934 (19)	C4C—H4C	0.870 (18)
C12A—C13A	1.376 (3)	C5C—H5C	0.929 (18)
C12A—H12A	0.93 (2)	C6C—H6C	0.983 (17)
C13A—C14A	1.372 (3)	C1D—S1D	1.773 (3)
C13A—H13A	0.96 (2)	C1D—H1D	0.92 (3)
C14A—H14A	0.965 (17)	C1D—H2D	1.01 (3)
N1B—C2B	1.343 (2)	C1D—H3D	0.95 (3)
N1B—C8AB	1.348 (2)	O1D—S1D	1.4957 (13)
C2B—N2B	1.344 (2)	S1D—C2D	1.782 (2)
C2B—N3B	1.368 (2)	C2D—H4D	0.95 (3)
N2B—H2B	0.92 (2)	C2D—H5D	0.97 (3)
N2B—H3B	0.903 (19)	C2D—H6D	0.96 (2)
N3B—C4B	1.331 (2)	C1E—S1E	1.769 (2)
C4B—N4B	1.338 (2)	C1E—H1E	0.92 (2)
C4B—C4AB	1.430 (2)	C1E—H2E	0.94 (2)
N4B—H4B	0.921 (19)	C1E—H3E	0.94 (2)
N4B—H5B	0.881 (19)	O1E—S1E	1.5029 (13)
C4AB—N5B	1.351 (2)	S1E—C2E	1.784 (2)
C4AB—C8AB	1.408 (2)	C2E—H4E	0.96 (2)
N5B—C6B	1.321 (2)	C2E—H5E	0.94 (3)
C6B—C7B	1.458 (2)	C2E—H6E	0.95 (2)
C8AA—N1A—C2A	119.95 (14)	C7B—N7B—H6B	121.8 (12)
C8AA—N1A—H1XA	126.3 (12)	C7B—N7B—H7B	116.9 (12)
C2A—N1A—H1XA	113.5 (12)	H6B—N7B—H7B	120.7 (17)
N2A—C2A—N3A	119.63 (15)	C7B—N8B—C8AB	117.94 (13)
N2A—C2A—N1A	117.17 (15)	N1B—C8AB—N8B	117.74 (14)
N3A—C2A—N1A	123.19 (16)	N1B—C8AB—C4AB	123.09 (14)
C2A—N2A—H2A	120.2 (12)	N8B—C8AB—C4AB	119.15 (16)
C2A—N2A—H3A	122.3 (12)	C10B—C9B—C14B	117.94 (17)
H2A—N2A—H3A	117.2 (17)	C10B—C9B—C6B	118.94 (16)
C4A—N3A—C2A	118.47 (13)	C14B—C9B—C6B	123.11 (15)
N4A—C4A—N3A	119.68 (16)	C11B—C10B—C9B	121.24 (19)
N4A—C4A—C4AA	119.30 (17)	C11B—C10B—H10B	121.2 (10)
N3A—C4A—C4AA	121.01 (14)	C9B—C10B—H10B	117.5 (10)
C4A—N4A—H4A	120.9 (12)	C12B—C11B—C10B	120.44 (19)
C4A—N4A—H5A	118.3 (12)	C12B—C11B—H11B	119.9 (12)
H4A—N4A—H5A	120.1 (17)	C10B—C11B—H11B	119.6 (12)
N5A—C4AA—C8AA	121.35 (14)	C11B—C12B—C13B	119.6 (2)
N5A—C4AA—C4A	120.54 (14)	C11B—C12B—H12B	122.9 (11)
C8AA—C4AA—C4A	118.06 (16)	C13B—C12B—H12B	117.4 (11)
C6A—N5A—C4AA	118.74 (14)	C12B—C13B—C14B	120.18 (19)
N5A—C6A—C7A	119.23 (16)	C12B—C13B—H13B	121.4 (10)
N5A—C6A—C9A	115.77 (14)	C14B—C13B—H13B	118.3 (10)
C7A—C6A—C9A	125.01 (14)	C13B—C14B—C9B	120.53 (18)
N7A—C7A—N8A	117.03 (15)	C13B—C14B—H14B	119.6 (10)
N7A—C7A—C6A	121.34 (17)	C9B—C14B—H14B	119.8 (10)
N8A—C7A—C6A	121.63 (14)	O2C—C1C—O1C	125.19 (17)
C7A—N7A—H6A	120.3 (10)	O2C—C1C—C2C	117.64 (17)
C7A—N7A—H7A	119.1 (13)	O1C—C1C—C2C	117.15 (16)
H6A—N7A—H7A	120.6 (17)	C5C—N1C—C6C	116.08 (17)
C7A—N8A—C8AA	116.58 (13)	C3C—C2C—C6C	117.54 (17)
N8A—C8AA—N1A	118.79 (14)	C3C—C2C—C1C	121.71 (16)
N8A—C8AA—C4AA	122.18 (16)	C6C—C2C—C1C	120.73 (17)
N1A—C8AA—C4AA	119.03 (15)	C4C—C3C—C2C	119.26 (18)
C10A—C9A—C14A	117.82 (17)	C4C—C3C—H3C	123.4 (10)
C10A—C9A—C6A	122.99 (15)	C2C—C3C—H3C	117.4 (10)
C14A—C9A—C6A	118.89 (16)	C3C—C4C—C5C	118.8 (2)
C11A—C10A—C9A	120.68 (18)	C3C—C4C—H4C	121.2 (12)
C11A—C10A—H10A	119.8 (10)	C5C—C4C—H4C	120.0 (12)
C9A—C10A—H10A	119.3 (10)	N1C—C5C—C4C	124.0 (2)
C12A—C11A—C10A	120.4 (2)	N1C—C5C—H5C	116.5 (11)
C12A—C11A—H11A	119.8 (11)	C4C—C5C—H5C	119.5 (11)
C10A—C11A—H11A	119.8 (11)	N1C—C6C—C2C	124.26 (18)
C13A—C12A—C11A	119.4 (2)	N1C—C6C—H6C	112.6 (9)
C13A—C12A—H12A	122.0 (12)	C2C—C6C—H6C	123.1 (9)
C11A—C12A—H12A	118.6 (12)	S1D—C1D—H1D	107.0 (15)
C14A—C13A—C12A	120.6 (2)	S1D—C1D—H2D	107.1 (16)
C14A—C13A—H13A	121.5 (13)	H1D—C1D—H2D	111 (2)
C12A—C13A—H13A	117.9 (13)	S1D—C1D—H3D	106.4 (16)
C13A—C14A—C9A	121.05 (19)	H1D—C1D—H3D	105 (2)
C13A—C14A—H14A	122.6 (10)	H2D—C1D—H3D	119 (2)
C9A—C14A—H14A	116.3 (10)	O1D—S1D—C1D	106.96 (16)
C2B—N1B—C8AB	115.26 (13)	O1D—S1D—C2D	107.10 (11)
N1B—C2B—N2B	117.55 (15)	C1D—S1D—C2D	97.41 (14)
N1B—C2B—N3B	127.43 (16)	S1D—C2D—H4D	106.3 (14)
N2B—C2B—N3B	115.01 (15)	S1D—C2D—H5D	107.2 (13)
C2B—N2B—H2B	119.9 (12)	H4D—C2D—H5D	115 (2)
C2B—N2B—H3B	120.2 (12)	S1D—C2D—H6D	109.2 (13)
H2B—N2B—H3B	114.1 (17)	H4D—C2D—H6D	107 (2)
C4B—N3B—C2B	116.36 (13)	H5D—C2D—H6D	112.0 (19)
N3B—C4B—N4B	118.61 (15)	S1E—C1E—H1E	107.2 (14)
N3B—C4B—C4AB	121.66 (14)	S1E—C1E—H2E	106.4 (12)
N4B—C4B—C4AB	119.73 (17)	H1E—C1E—H2E	109.2 (18)
C4B—N4B—H4B	117.5 (11)	S1E—C1E—H3E	112.4 (13)
C4B—N4B—H5B	118.3 (11)	H1E—C1E—H3E	109.9 (19)
H4B—N4B—H5B	123.2 (16)	H2E—C1E—H3E	111.7 (17)
N5B—C4AB—C8AB	122.90 (14)	O1E—S1E—C1E	106.18 (11)
N5B—C4AB—C4B	121.00 (14)	O1E—S1E—C2E	105.70 (11)
C8AB—C4AB—C4B	116.10 (15)	C1E—S1E—C2E	97.43 (13)
C6B—N5B—C4AB	118.75 (13)	S1E—C2E—H4E	106.2 (12)
N5B—C6B—C7B	118.90 (15)	S1E—C2E—H5E	104.6 (13)
N5B—C6B—C9B	118.54 (14)	H4E—C2E—H5E	112.4 (19)
C7B—C6B—C9B	122.47 (14)	S1E—C2E—H6E	108.2 (12)
N8B—C7B—N7B	117.15 (15)	H4E—C2E—H6E	114.0 (18)
N8B—C7B—C6B	122.36 (14)	H5E—C2E—H6E	110.9 (18)
N7B—C7B—C6B	120.45 (17)
C8AA—N1A—C2A—N2A	−176.04 (16)	N3B—C4B—C4AB—N5B	−176.78 (15)
C8AA—N1A—C2A—N3A	4.8 (2)	N4B—C4B—C4AB—N5B	2.9 (2)
N2A—C2A—N3A—C4A	179.82 (16)	N3B—C4B—C4AB—C8AB	4.0 (2)
N1A—C2A—N3A—C4A	−1.1 (2)	N4B—C4B—C4AB—C8AB	−176.39 (16)
C2A—N3A—C4A—N4A	177.40 (16)	C8AB—C4AB—N5B—C6B	0.4 (2)
C2A—N3A—C4A—C4AA	−3.8 (2)	C4B—C4AB—N5B—C6B	−178.79 (15)
N4A—C4A—C4AA—N5A	6.2 (3)	C4AB—N5B—C6B—C7B	0.2 (2)
N3A—C4A—C4AA—N5A	−172.61 (15)	C4AB—N5B—C6B—C9B	−176.38 (14)
N4A—C4A—C4AA—C8AA	−176.31 (16)	N5B—C6B—C7B—N8B	−0.9 (2)
N3A—C4A—C4AA—C8AA	4.9 (2)	C9B—C6B—C7B—N8B	175.60 (16)
C8AA—C4AA—N5A—C6A	0.5 (2)	N5B—C6B—C7B—N7B	−178.56 (17)
C4A—C4AA—N5A—C6A	177.86 (15)	C9B—C6B—C7B—N7B	−2.1 (3)
C4AA—N5A—C6A—C7A	4.1 (2)	N7B—C7B—N8B—C8AB	178.58 (16)
C4AA—N5A—C6A—C9A	−175.86 (15)	C6B—C7B—N8B—C8AB	0.8 (2)
N5A—C6A—C7A—N7A	173.67 (16)	C2B—N1B—C8AB—N8B	178.99 (14)
C9A—C6A—C7A—N7A	−6.3 (3)	C2B—N1B—C8AB—C4AB	0.7 (2)
N5A—C6A—C7A—N8A	−5.6 (2)	C7B—N8B—C8AB—N1B	−178.58 (15)
C9A—C6A—C7A—N8A	174.43 (16)	C7B—N8B—C8AB—C4AB	−0.2 (2)
N7A—C7A—N8A—C8AA	−177.36 (15)	N5B—C4AB—C8AB—N1B	177.86 (15)
C6A—C7A—N8A—C8AA	1.9 (2)	C4B—C4AB—C8AB—N1B	−2.9 (2)
C7A—N8A—C8AA—N1A	−177.78 (15)	N5B—C4AB—C8AB—N8B	−0.4 (2)
C7A—N8A—C8AA—C4AA	2.8 (2)	C4B—C4AB—C8AB—N8B	178.77 (15)
C2A—N1A—C8AA—N8A	177.11 (15)	N5B—C6B—C9B—C10B	41.8 (2)
C2A—N1A—C8AA—C4AA	−3.5 (2)	C7B—C6B—C9B—C10B	−134.70 (17)
N5A—C4AA—C8AA—N8A	−4.3 (3)	N5B—C6B—C9B—C14B	−137.09 (17)
C4A—C4AA—C8AA—N8A	178.27 (15)	C7B—C6B—C9B—C14B	46.4 (2)
N5A—C4AA—C8AA—N1A	176.34 (15)	C14B—C9B—C10B—C11B	−1.1 (3)
C4A—C4AA—C8AA—N1A	−1.1 (2)	C6B—C9B—C10B—C11B	179.92 (15)
N5A—C6A—C9A—C10A	136.32 (17)	C9B—C10B—C11B—C12B	1.4 (3)
C7A—C6A—C9A—C10A	−43.7 (3)	C10B—C11B—C12B—C13B	−0.4 (3)
N5A—C6A—C9A—C14A	−37.3 (2)	C11B—C12B—C13B—C14B	−0.6 (3)
C7A—C6A—C9A—C14A	142.73 (17)	C12B—C13B—C14B—C9B	0.8 (3)
C14A—C9A—C10A—C11A	−0.3 (3)	C10B—C9B—C14B—C13B	0.1 (2)
C6A—C9A—C10A—C11A	−173.98 (16)	C6B—C9B—C14B—C13B	178.95 (15)
C9A—C10A—C11A—C12A	0.1 (3)	O2C—C1C—C2C—C3C	0.9 (3)
C10A—C11A—C12A—C13A	0.2 (3)	O1C—C1C—C2C—C3C	179.43 (16)
C11A—C12A—C13A—C14A	−0.3 (3)	O2C—C1C—C2C—C6C	−177.38 (16)
C12A—C13A—C14A—C9A	0.1 (3)	O1C—C1C—C2C—C6C	1.2 (2)
C10A—C9A—C14A—C13A	0.2 (3)	C6C—C2C—C3C—C4C	0.1 (3)
C6A—C9A—C14A—C13A	174.13 (18)	C1C—C2C—C3C—C4C	−178.17 (17)
C8AB—N1B—C2B—N2B	−177.61 (15)	C2C—C3C—C4C—C5C	1.5 (3)
C8AB—N1B—C2B—N3B	0.9 (2)	C6C—N1C—C5C—C4C	0.0 (3)
N1B—C2B—N3B—C4B	0.2 (2)	C3C—C4C—C5C—N1C	−1.7 (3)
N2B—C2B—N3B—C4B	178.69 (15)	C5C—N1C—C6C—C2C	1.8 (3)
C2B—N3B—C4B—N4B	177.67 (15)	C3C—C2C—C6C—N1C	−1.9 (3)
C2B—N3B—C4B—C4AB	−2.7 (2)	C1C—C2C—C6C—N1C	176.45 (16)

Triamterene and Ibuprofen, DMSO solvate (1g_DMSO)

Crystal data

C12H12N7^+·C12H11N7·C13H17O2^−·C2H6OS	Z = 2
Mr = 790.96	F(000) = 836
Triclinic, P1	Dx = 1.294 Mg m^−3
a = 11.2398 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.2439 (3) Å	Cell parameters from 53045 reflections
c = 15.4624 (4) Å	θ = 1.0–27.5°
α = 113.595 (2)°	µ = 0.14 mm^−1
β = 103.527 (3)°	T = 180 K
γ = 91.977 (2)°	Block, colourless
V = 2029.46 (10) Å^3	0.30 × 0.14 × 0.10 mm

Data collection

Nonius Kappa CCD diffractometer	9204 independent reflections
Radiation source: fine-focus sealed tube	6189 reflections with I > 2σ(I)
None monochromator	Rint = 0.041
Thin slice ω and φ scans	θmax = 27.5°, θmin = 2.4°
Absorption correction: multi-scan multi-scan from symmetry-related measurements Sortav (Blessing 1995)	h = −14→14
Tmin = 0.880, Tmax = 0.991	k = −17→16
30734 measured reflections	l = −19→20

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.074	Hydrogen site location: mixed
wR(F^2) = 0.215	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0959P)^2 + 1.9185P] where P = (Fo^2 + 2Fc^2)/3
9204 reflections	(Δ/σ)max < 0.001
626 parameters	Δρmax = 1.23 e Å^−3
0 restraints	Δρmin = −0.42 e Å^−3

Special details

Experimental. Poor crystals, poor data (mosaicity 1.3degrees). The -NH(+) hydrogen atom was NOT located reliably but placed on atom N1 because (a) the C-O distances indicate that the Ibuprofen is deprotonated, (b) this position makes the best H-bonds and (c) this position is in line with other protonated Triamterene structures. The DMSO solvate is disordered about two sites (occupancies 0.9 : 0.1). For the refinement, geometric constraints and a common isotropic displacement parameter for the non-H atoms were applied to the minor site.

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)
N1A	0.1580 (2)	0.58904 (19)	0.05356 (16)	0.0349 (5)
C2A	0.2523 (2)	0.5292 (2)	0.06433 (18)	0.0336 (5)
N2A	0.2557 (2)	0.4802 (2)	0.12371 (17)	0.0386 (5)
N3A	0.3413 (2)	0.51942 (18)	0.01767 (15)	0.0343 (5)
C4A	0.3353 (2)	0.5687 (2)	−0.04378 (18)	0.0327 (5)
N4A	0.4246 (2)	0.5613 (2)	−0.08795 (18)	0.0401 (5)
C4AA	0.2359 (2)	0.6294 (2)	−0.06092 (18)	0.0327 (5)
N5A	0.2315 (2)	0.67980 (18)	−0.12262 (15)	0.0354 (5)
C6A	0.1412 (3)	0.7376 (2)	−0.13250 (19)	0.0362 (6)
C7A	0.0465 (3)	0.7437 (2)	−0.0816 (2)	0.0393 (6)
N7A	−0.0486 (3)	0.7979 (2)	−0.0944 (2)	0.0508 (7)
N8A	0.0521 (2)	0.69449 (19)	−0.01987 (16)	0.0381 (5)
C8AA	0.1472 (2)	0.6391 (2)	−0.01040 (18)	0.0336 (5)
C9A	0.1409 (3)	0.7963 (2)	−0.1967 (2)	0.0395 (6)
C10A	0.1512 (3)	0.7379 (3)	−0.2910 (2)	0.0480 (7)
C11A	0.1598 (4)	0.7914 (3)	−0.3503 (3)	0.0587 (9)
C12A	0.1607 (4)	0.9050 (3)	−0.3145 (3)	0.0630 (10)
C13A	0.1512 (4)	0.9647 (3)	−0.2207 (3)	0.0623 (9)
C14A	0.1393 (3)	0.9106 (3)	−0.1624 (2)	0.0499 (7)
N1B	0.9051 (2)	0.48861 (18)	0.75212 (15)	0.0356 (5)
C2B	0.8819 (2)	0.5190 (2)	0.67762 (19)	0.0352 (6)
N2B	0.7901 (3)	0.5808 (2)	0.6725 (2)	0.0483 (7)
N3B	0.9400 (2)	0.49352 (19)	0.60561 (15)	0.0366 (5)
C4B	1.0342 (2)	0.4349 (2)	0.61084 (18)	0.0345 (6)
N4B	1.0957 (3)	0.4103 (2)	0.54329 (19)	0.0473 (6)
C4AB	1.0680 (2)	0.3989 (2)	0.68796 (18)	0.0317 (5)
N5B	1.16367 (19)	0.34036 (18)	0.69376 (15)	0.0333 (5)
C6B	1.1881 (2)	0.3055 (2)	0.76368 (18)	0.0325 (5)
C7B	1.1102 (2)	0.3273 (2)	0.83063 (18)	0.0322 (5)
N7B	1.1227 (2)	0.2821 (2)	0.89521 (17)	0.0385 (5)
N8B	1.0186 (2)	0.38842 (17)	0.82688 (15)	0.0331 (5)
C8AB	0.9974 (2)	0.4264 (2)	0.75588 (17)	0.0310 (5)
C9B	1.2899 (2)	0.2372 (2)	0.7657 (2)	0.0365 (6)
C10B	1.3742 (3)	0.2482 (3)	0.8513 (2)	0.0436 (7)
C11B	1.4680 (3)	0.1816 (3)	0.8485 (3)	0.0530 (8)
C12B	1.4773 (3)	0.1036 (3)	0.7601 (3)	0.0569 (9)
C13B	1.3954 (3)	0.0930 (3)	0.6746 (3)	0.0550 (8)
C14B	1.3019 (3)	0.1583 (3)	0.6761 (2)	0.0442 (7)
C1C	0.3513 (3)	0.2246 (3)	0.0917 (3)	0.0511 (8)
O1C	0.2561 (2)	0.1976 (2)	0.02344 (17)	0.0569 (6)
C2C	0.4081 (4)	0.1283 (4)	0.1095 (4)	0.0796 (13)
H1C	0.3893	0.0651	0.0429	0.095*
O2C	0.4016 (2)	0.3234 (2)	0.1472 (2)	0.0660 (7)
C3C	0.5376 (4)	0.1430 (5)	0.1459 (6)	0.130 (3)
H2C	0.5638	0.2082	0.2091	0.195*
H3C	0.5765	0.1542	0.0993	0.195*
H4C	0.5625	0.0768	0.1546	0.195*
C4C	0.3337 (4)	0.0902 (3)	0.1650 (3)	0.0596 (9)
C5C	0.3407 (5)	0.1532 (3)	0.2619 (4)	0.0902 (14)
H5C	0.3918	0.2235	0.2958	0.108*
C6C	0.2734 (5)	0.1155 (3)	0.3119 (3)	0.0887 (15)
H6C	0.2800	0.1609	0.3789	0.106*
C7C	0.2004 (4)	0.0173 (3)	0.2675 (3)	0.0694 (11)
C8C	0.1885 (4)	−0.0428 (4)	0.1704 (3)	0.0732 (11)
H8C	0.1342	−0.1113	0.1362	0.088*
C9C	0.2535 (4)	−0.0068 (4)	0.1203 (3)	0.0678 (10)
H9C	0.2421	−0.0510	0.0524	0.081*
C10C	0.1327 (5)	−0.0260 (5)	0.3231 (4)	0.0959 (16)
H11C	0.1085	0.0384	0.3727	0.115*
H10C	0.0556	−0.0741	0.2762	0.115*
C11C	0.1976 (5)	−0.0868 (4)	0.3712 (4)	0.0923 (15)
H12C	0.2668	−0.0296	0.4227	0.111*
C12C	0.1212 (6)	−0.1144 (4)	0.4320 (4)	0.1084 (19)
H13C	0.0875	−0.0481	0.4686	0.163*
H14C	0.1744	−0.1384	0.4780	0.163*
H15C	0.0531	−0.1744	0.3880	0.163*
C13C	0.2597 (5)	−0.1758 (4)	0.3250 (4)	0.0985 (16)
H16C	0.1989	−0.2413	0.2794	0.148*
H17C	0.3144	−0.1937	0.3748	0.148*
H18C	0.3088	−0.1541	0.2889	0.148*
S1D	0.55329 (9)	0.57198 (8)	0.43456 (7)	0.0535 (3)	0.91
O1D	0.6714 (7)	0.6402 (3)	0.5071 (4)	0.0537 (10)	0.91
C1D	0.5264 (5)	0.6190 (5)	0.3393 (4)	0.0719 (14)	0.91
H1D	0.5067	0.6952	0.3646	0.108*	0.91
H2D	0.4570	0.5700	0.2847	0.108*	0.91
H3D	0.6007	0.6176	0.3162	0.108*	0.91
C2D	0.5957 (6)	0.4417 (4)	0.3651 (5)	0.1042 (18)	0.91
H4D	0.6174	0.4012	0.4062	0.156*	0.91
H5D	0.6669	0.4544	0.3425	0.156*	0.91
H6D	0.5260	0.3977	0.3083	0.156*	0.91
S1D'	0.5666 (12)	0.6911 (11)	0.4585 (9)	0.076 (3)*	0.09
O1D'	0.668 (10)	0.616 (6)	0.497 (7)	0.076 (3)*	0.09
C1D'	0.431 (4)	0.662 (4)	0.485 (4)	0.076 (3)*	0.09
H1D'	0.4316	0.5922	0.4935	0.115*	0.09
H2D'	0.3597	0.6543	0.4316	0.115*	0.09
H3D'	0.4254	0.7227	0.5462	0.115*	0.09
C2D'	0.483 (6)	0.633 (6)	0.357 (5)	0.076 (3)*	0.09
H4D'	0.3983	0.6200	0.3606	0.115*	0.09
H5D'	0.5103	0.5623	0.3229	0.115*	0.09
H6D'	0.4858	0.6803	0.3221	0.115*	0.09
H1XA	0.103 (3)	0.595 (3)	0.085 (2)	0.046 (9)*
H2A	0.198 (3)	0.486 (2)	0.152 (2)	0.036 (7)*
H3A	0.307 (3)	0.429 (3)	0.122 (2)	0.056 (10)*
H4A	0.489 (3)	0.529 (3)	−0.074 (2)	0.050 (9)*
H5A	0.432 (3)	0.604 (3)	−0.121 (2)	0.047 (8)*
H6A	−0.051 (3)	0.831 (3)	−0.139 (3)	0.061 (10)*
H7A	−0.112 (3)	0.797 (3)	−0.066 (3)	0.055 (9)*
H10A	0.151 (3)	0.665 (3)	−0.312 (2)	0.045 (8)*
H11A	0.170 (3)	0.751 (3)	−0.418 (3)	0.064 (10)*
H12A	0.161 (3)	0.939 (3)	−0.357 (3)	0.067 (10)*
H13A	0.147 (3)	1.044 (3)	−0.193 (3)	0.066 (10)*
H14A	0.136 (3)	0.955 (3)	−0.098 (3)	0.055 (9)*
H2B	0.753 (3)	0.596 (3)	0.713 (3)	0.048 (9)*
H3B	0.771 (3)	0.603 (3)	0.625 (2)	0.046 (8)*
H4B	1.079 (3)	0.436 (3)	0.499 (3)	0.055 (9)*
H5B	1.160 (3)	0.374 (3)	0.546 (2)	0.045 (8)*
H6B	1.182 (3)	0.250 (2)	0.909 (2)	0.035 (8)*
H7B	1.072 (3)	0.297 (3)	0.932 (2)	0.043 (8)*
H10B	1.369 (2)	0.300 (2)	0.910 (2)	0.032 (7)*
H11B	1.521 (3)	0.194 (3)	0.912 (3)	0.056 (9)*
H12B	1.538 (3)	0.057 (3)	0.760 (3)	0.065 (10)*
H13B	1.399 (4)	0.044 (3)	0.616 (3)	0.071 (12)*
H14B	1.245 (3)	0.154 (2)	0.613 (2)	0.043 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0382 (12)	0.0453 (13)	0.0343 (12)	0.0144 (10)	0.0166 (10)	0.0254 (10)
C2A	0.0378 (14)	0.0375 (13)	0.0323 (13)	0.0088 (11)	0.0127 (11)	0.0194 (11)
N2A	0.0418 (13)	0.0517 (14)	0.0422 (13)	0.0193 (11)	0.0223 (11)	0.0324 (11)
N3A	0.0359 (11)	0.0396 (11)	0.0371 (12)	0.0094 (9)	0.0143 (9)	0.0232 (10)
C4A	0.0367 (13)	0.0342 (13)	0.0323 (13)	0.0042 (10)	0.0101 (10)	0.0186 (11)
N4A	0.0404 (13)	0.0518 (14)	0.0485 (14)	0.0164 (11)	0.0215 (11)	0.0355 (12)
C4AA	0.0369 (13)	0.0361 (13)	0.0318 (13)	0.0055 (11)	0.0100 (10)	0.0205 (11)
N5A	0.0425 (12)	0.0362 (11)	0.0343 (11)	0.0066 (9)	0.0119 (9)	0.0208 (10)
C6A	0.0416 (14)	0.0384 (13)	0.0338 (13)	0.0064 (11)	0.0098 (11)	0.0207 (11)
C7A	0.0461 (15)	0.0432 (15)	0.0359 (14)	0.0121 (12)	0.0118 (12)	0.0230 (12)
N7A	0.0527 (16)	0.0719 (18)	0.0561 (16)	0.0310 (14)	0.0253 (13)	0.0474 (15)
N8A	0.0416 (12)	0.0470 (13)	0.0387 (12)	0.0147 (10)	0.0161 (10)	0.0276 (11)
C8AA	0.0397 (14)	0.0373 (13)	0.0291 (12)	0.0079 (11)	0.0109 (10)	0.0182 (11)
C9A	0.0439 (15)	0.0423 (14)	0.0421 (15)	0.0075 (12)	0.0109 (12)	0.0278 (13)
C10A	0.063 (2)	0.0433 (17)	0.0456 (17)	0.0044 (14)	0.0171 (14)	0.0259 (14)
C11A	0.076 (2)	0.067 (2)	0.0473 (19)	0.0060 (18)	0.0208 (17)	0.0357 (17)
C12A	0.079 (2)	0.068 (2)	0.060 (2)	0.0029 (18)	0.0133 (18)	0.049 (2)
C13A	0.083 (3)	0.0458 (18)	0.066 (2)	0.0089 (17)	0.0101 (19)	0.0369 (17)
C14A	0.067 (2)	0.0464 (17)	0.0437 (17)	0.0135 (15)	0.0113 (15)	0.0274 (15)
N1B	0.0428 (12)	0.0429 (12)	0.0340 (11)	0.0140 (10)	0.0161 (10)	0.0253 (10)
C2B	0.0394 (14)	0.0406 (14)	0.0356 (13)	0.0114 (11)	0.0121 (11)	0.0245 (12)
N2B	0.0581 (16)	0.0696 (17)	0.0448 (14)	0.0339 (14)	0.0265 (13)	0.0427 (14)
N3B	0.0422 (12)	0.0474 (13)	0.0332 (11)	0.0151 (10)	0.0140 (9)	0.0272 (10)
C4B	0.0397 (14)	0.0408 (14)	0.0323 (13)	0.0092 (11)	0.0125 (11)	0.0229 (11)
N4B	0.0533 (15)	0.0710 (17)	0.0462 (14)	0.0318 (14)	0.0271 (12)	0.0439 (14)
C4AB	0.0363 (13)	0.0350 (12)	0.0308 (12)	0.0076 (10)	0.0104 (10)	0.0198 (11)
N5B	0.0366 (11)	0.0384 (11)	0.0331 (11)	0.0078 (9)	0.0109 (9)	0.0223 (10)
C6B	0.0372 (13)	0.0340 (13)	0.0321 (13)	0.0066 (10)	0.0099 (10)	0.0191 (11)
C7B	0.0371 (13)	0.0346 (13)	0.0294 (12)	0.0046 (10)	0.0085 (10)	0.0183 (11)
N7B	0.0431 (13)	0.0492 (14)	0.0394 (13)	0.0176 (11)	0.0161 (11)	0.0313 (11)
N8B	0.0390 (12)	0.0378 (11)	0.0318 (11)	0.0103 (9)	0.0122 (9)	0.0222 (9)
C8AB	0.0368 (13)	0.0320 (12)	0.0295 (12)	0.0051 (10)	0.0096 (10)	0.0177 (10)
C9B	0.0375 (14)	0.0416 (14)	0.0436 (15)	0.0091 (11)	0.0137 (11)	0.0293 (12)
C10B	0.0426 (16)	0.0487 (16)	0.0498 (18)	0.0117 (13)	0.0118 (13)	0.0308 (15)
C11B	0.0448 (17)	0.064 (2)	0.067 (2)	0.0155 (15)	0.0116 (16)	0.0463 (18)
C12B	0.0543 (19)	0.062 (2)	0.084 (3)	0.0295 (16)	0.0315 (18)	0.051 (2)
C13B	0.063 (2)	0.060 (2)	0.063 (2)	0.0280 (17)	0.0329 (18)	0.0368 (18)
C14B	0.0492 (17)	0.0516 (17)	0.0471 (17)	0.0200 (14)	0.0215 (14)	0.0303 (14)
C1C	0.0481 (18)	0.064 (2)	0.080 (2)	0.0255 (16)	0.0347 (17)	0.0582 (19)
O1C	0.0631 (14)	0.0714 (15)	0.0619 (14)	0.0239 (12)	0.0240 (12)	0.0486 (13)
C2C	0.075 (3)	0.102 (3)	0.132 (4)	0.053 (2)	0.054 (3)	0.102 (3)
O2C	0.0498 (13)	0.0761 (17)	0.0969 (19)	0.0133 (12)	0.0128 (13)	0.0648 (16)
C3C	0.070 (3)	0.141 (5)	0.248 (8)	0.032 (3)	0.036 (4)	0.154 (6)
C4C	0.078 (2)	0.064 (2)	0.072 (2)	0.0378 (19)	0.0321 (19)	0.055 (2)
C5C	0.139 (4)	0.044 (2)	0.094 (3)	−0.001 (2)	0.033 (3)	0.036 (2)
C6C	0.155 (5)	0.055 (2)	0.065 (3)	0.017 (3)	0.047 (3)	0.025 (2)
C7C	0.094 (3)	0.067 (2)	0.081 (3)	0.033 (2)	0.043 (2)	0.053 (2)
C8C	0.071 (2)	0.098 (3)	0.066 (2)	−0.002 (2)	0.0064 (19)	0.059 (2)
C9C	0.068 (2)	0.092 (3)	0.058 (2)	0.004 (2)	0.0090 (17)	0.052 (2)
C10C	0.108 (4)	0.126 (4)	0.115 (4)	0.044 (3)	0.063 (3)	0.092 (3)
C11C	0.149 (5)	0.071 (3)	0.099 (3)	0.021 (3)	0.069 (3)	0.057 (3)
C12C	0.175 (6)	0.089 (3)	0.090 (3)	−0.002 (3)	0.071 (4)	0.049 (3)
C13C	0.083 (3)	0.106 (4)	0.151 (5)	0.018 (3)	0.041 (3)	0.093 (4)
S1D	0.0589 (6)	0.0615 (5)	0.0522 (5)	0.0103 (4)	0.0166 (4)	0.0348 (4)
O1D	0.0607 (17)	0.060 (3)	0.0397 (18)	0.024 (2)	0.0108 (14)	0.0200 (19)
C1D	0.069 (3)	0.092 (3)	0.064 (3)	0.006 (3)	0.006 (2)	0.049 (3)
C2D	0.104 (4)	0.068 (3)	0.114 (4)	0.015 (3)	0.010 (3)	0.021 (3)

Geometric parameters (Å, º)

N1A—C2A	1.364 (3)	C11B—C12B	1.374 (5)
N1A—C8AA	1.381 (3)	C11B—H11B	0.96 (4)
N1A—H1XA	0.86 (3)	C12B—C13B	1.374 (5)
C2A—N2A	1.314 (3)	C12B—H12B	0.93 (4)
C2A—N3A	1.346 (3)	C13B—C14B	1.382 (4)
N2A—H2A	0.86 (3)	C13B—H13B	0.89 (4)
N2A—H3A	0.90 (4)	C14B—H14B	1.01 (3)
N3A—C4A	1.343 (3)	C1C—O1C	1.237 (4)
C4A—N4A	1.326 (3)	C1C—O2C	1.261 (4)
C4A—C4AA	1.434 (4)	C1C—C2C	1.538 (4)
N4A—H4A	0.88 (3)	C2C—C3C	1.407 (6)
N4A—H5A	0.92 (3)	C2C—C4C	1.531 (5)
C4AA—N5A	1.360 (3)	C2C—H1C	1.0000
C4AA—C8AA	1.383 (4)	C3C—H2C	0.9800
N5A—C6A	1.308 (3)	C3C—H3C	0.9800
C6A—C7A	1.452 (4)	C3C—H4C	0.9800
C6A—C9A	1.485 (3)	C4C—C9C	1.363 (5)
C7A—N7A	1.328 (4)	C4C—C5C	1.375 (6)
C7A—N8A	1.346 (3)	C5C—C6C	1.405 (6)
N7A—H6A	0.95 (4)	C5C—H5C	0.9500
N7A—H7A	0.92 (4)	C6C—C7C	1.335 (6)
N8A—C8AA	1.331 (3)	C6C—H6C	0.9500
C9A—C10A	1.386 (4)	C7C—C8C	1.360 (6)
C9A—C14A	1.392 (4)	C7C—C10C	1.522 (5)
C10A—C11A	1.382 (4)	C8C—C9C	1.377 (5)
C10A—H10A	0.88 (3)	C8C—H8C	0.9500
C11A—C12A	1.378 (5)	C9C—H9C	0.9500
C11A—H11A	1.00 (4)	C10C—C11C	1.414 (6)
C12A—C13A	1.378 (5)	C10C—H11C	0.9900
C12A—H12A	0.94 (4)	C10C—H10C	0.9900
C13A—C14A	1.383 (4)	C11C—C13C	1.415 (7)
C13A—H13A	0.98 (4)	C11C—C12C	1.545 (6)
C14A—H14A	0.94 (3)	C11C—H12C	1.0000
N1B—C2B	1.340 (3)	C12C—H13C	0.9800
N1B—C8AB	1.352 (3)	C12C—H14C	0.9800
C2B—N2B	1.346 (4)	C12C—H15C	0.9800
C2B—N3B	1.355 (3)	C13C—H16C	0.9800
N2B—H2B	0.80 (3)	C13C—H17C	0.9800
N2B—H3B	0.89 (3)	C13C—H18C	0.9800
N3B—C4B	1.341 (3)	S1D—O1D	1.498 (7)
C4B—N4B	1.325 (3)	S1D—C2D	1.781 (5)
C4B—C4AB	1.432 (3)	S1D—C1D	1.786 (5)
N4B—H4B	0.87 (4)	C1D—H1D	0.9800
N4B—H5B	0.89 (3)	C1D—H2D	0.9800
C4AB—N5B	1.354 (3)	C1D—H3D	0.9800
C4AB—C8AB	1.403 (3)	C2D—H4D	0.9800
N5B—C6B	1.314 (3)	C2D—H5D	0.9800
C6B—C7B	1.457 (3)	C2D—H6D	0.9800
C6B—C9B	1.485 (3)	S1D'—C2D'	1.49 (7)
C7B—N8B	1.336 (3)	S1D'—O1D'	1.69 (9)
C7B—N7B	1.339 (3)	S1D'—C1D'	1.74 (5)
N7B—H6B	0.83 (3)	C1D'—H1D'	0.9800
N7B—H7B	0.88 (3)	C1D'—H2D'	0.9800
N8B—C8AB	1.358 (3)	C1D'—H3D'	0.9800
C9B—C10B	1.385 (4)	C2D'—H4D'	0.9800
C9B—C14B	1.403 (4)	C2D'—H5D'	0.9800
C10B—C11B	1.395 (4)	C2D'—H6D'	0.9800
C10B—H10B	0.91 (3)
C2A—N1A—C8AA	120.5 (2)	C12B—C13B—C14B	120.9 (3)
C2A—N1A—H1XA	121 (2)	C12B—C13B—H13B	123 (3)
C8AA—N1A—H1XA	118 (2)	C14B—C13B—H13B	116 (3)
N2A—C2A—N3A	119.3 (2)	C13B—C14B—C9B	120.1 (3)
N2A—C2A—N1A	117.9 (2)	C13B—C14B—H14B	121.2 (17)
N3A—C2A—N1A	122.8 (2)	C9B—C14B—H14B	118.6 (17)
C2A—N2A—H2A	119.0 (19)	O1C—C1C—O2C	125.0 (3)
C2A—N2A—H3A	118 (2)	O1C—C1C—C2C	115.8 (3)
H2A—N2A—H3A	121 (3)	O2C—C1C—C2C	119.2 (3)
C4A—N3A—C2A	118.5 (2)	C3C—C2C—C4C	115.8 (4)
N4A—C4A—N3A	118.4 (2)	C3C—C2C—C1C	117.0 (4)
N4A—C4A—C4AA	120.2 (2)	C4C—C2C—C1C	108.3 (3)
N3A—C4A—C4AA	121.3 (2)	C3C—C2C—H1C	104.8
C4A—N4A—H4A	121 (2)	C4C—C2C—H1C	104.8
C4A—N4A—H5A	121 (2)	C1C—C2C—H1C	104.8
H4A—N4A—H5A	117 (3)	C2C—C3C—H2C	109.5
N5A—C4AA—C8AA	120.7 (2)	C2C—C3C—H3C	109.5
N5A—C4AA—C4A	120.8 (2)	H2C—C3C—H3C	109.5
C8AA—C4AA—C4A	118.5 (2)	C2C—C3C—H4C	109.5
C6A—N5A—C4AA	118.1 (2)	H2C—C3C—H4C	109.5
N5A—C6A—C7A	120.5 (2)	H3C—C3C—H4C	109.5
N5A—C6A—C9A	117.4 (2)	C9C—C4C—C5C	115.9 (3)
C7A—C6A—C9A	122.1 (2)	C9C—C4C—C2C	122.0 (4)
N7A—C7A—N8A	117.8 (2)	C5C—C4C—C2C	122.1 (4)
N7A—C7A—C6A	121.1 (2)	C4C—C5C—C6C	121.1 (4)
N8A—C7A—C6A	121.0 (2)	C4C—C5C—H5C	119.5
C7A—N7A—H6A	116 (2)	C6C—C5C—H5C	119.5
C7A—N7A—H7A	121 (2)	C7C—C6C—C5C	121.7 (4)
H6A—N7A—H7A	123 (3)	C7C—C6C—H6C	119.2
C8AA—N8A—C7A	116.1 (2)	C5C—C6C—H6C	119.2
N8A—C8AA—N1A	118.1 (2)	C6C—C7C—C8C	117.4 (4)
N8A—C8AA—C4AA	123.5 (2)	C6C—C7C—C10C	121.6 (4)
N1A—C8AA—C4AA	118.4 (2)	C8C—C7C—C10C	121.0 (4)
C10A—C9A—C14A	118.7 (3)	C7C—C8C—C9C	121.5 (4)
C10A—C9A—C6A	119.5 (2)	C7C—C8C—H8C	119.2
C14A—C9A—C6A	121.6 (3)	C9C—C8C—H8C	119.2
C11A—C10A—C9A	121.0 (3)	C4C—C9C—C8C	122.3 (4)
C11A—C10A—H10A	121 (2)	C4C—C9C—H9C	118.9
C9A—C10A—H10A	118 (2)	C8C—C9C—H9C	118.9
C12A—C11A—C10A	119.5 (3)	C11C—C10C—C7C	116.9 (4)
C12A—C11A—H11A	119 (2)	C11C—C10C—H11C	108.1
C10A—C11A—H11A	122 (2)	C7C—C10C—H11C	108.1
C13A—C12A—C11A	120.3 (3)	C11C—C10C—H10C	108.1
C13A—C12A—H12A	121 (2)	C7C—C10C—H10C	108.1
C11A—C12A—H12A	118 (2)	H11C—C10C—H10C	107.3
C12A—C13A—C14A	120.1 (3)	C10C—C11C—C13C	123.3 (4)
C12A—C13A—H13A	123 (2)	C10C—C11C—C12C	110.2 (5)
C14A—C13A—H13A	117 (2)	C13C—C11C—C12C	112.1 (4)
C13A—C14A—C9A	120.3 (3)	C10C—C11C—H12C	102.8
C13A—C14A—H14A	117 (2)	C13C—C11C—H12C	102.8
C9A—C14A—H14A	122 (2)	C12C—C11C—H12C	102.8
C2B—N1B—C8AB	116.1 (2)	C11C—C12C—H13C	109.5
N1B—C2B—N2B	117.0 (2)	C11C—C12C—H14C	109.5
N1B—C2B—N3B	127.2 (2)	H13C—C12C—H14C	109.5
N2B—C2B—N3B	115.9 (2)	C11C—C12C—H15C	109.5
C2B—N2B—H2B	118 (2)	H13C—C12C—H15C	109.5
C2B—N2B—H3B	120 (2)	H14C—C12C—H15C	109.5
H2B—N2B—H3B	122 (3)	C11C—C13C—H16C	109.5
C4B—N3B—C2B	116.9 (2)	C11C—C13C—H17C	109.5
N4B—C4B—N3B	119.0 (2)	H16C—C13C—H17C	109.5
N4B—C4B—C4AB	120.3 (2)	C11C—C13C—H18C	109.5
N3B—C4B—C4AB	120.7 (2)	H16C—C13C—H18C	109.5
C4B—N4B—H4B	121 (2)	H17C—C13C—H18C	109.5
C4B—N4B—H5B	121 (2)	O1D—S1D—C2D	105.1 (3)
H4B—N4B—H5B	117 (3)	O1D—S1D—C1D	105.6 (3)
N5B—C4AB—C8AB	122.2 (2)	C2D—S1D—C1D	95.9 (3)
N5B—C4AB—C4B	120.7 (2)	S1D—C1D—H1D	109.5
C8AB—C4AB—C4B	117.1 (2)	S1D—C1D—H2D	109.5
C6B—N5B—C4AB	118.5 (2)	H1D—C1D—H2D	109.5
N5B—C6B—C7B	119.7 (2)	S1D—C1D—H3D	109.5
N5B—C6B—C9B	117.4 (2)	H1D—C1D—H3D	109.5
C7B—C6B—C9B	122.7 (2)	H2D—C1D—H3D	109.5
N8B—C7B—N7B	116.8 (2)	S1D—C2D—H4D	109.5
N8B—C7B—C6B	121.6 (2)	S1D—C2D—H5D	109.5
N7B—C7B—C6B	121.5 (2)	H4D—C2D—H5D	109.5
C7B—N7B—H6B	124 (2)	S1D—C2D—H6D	109.5
C7B—N7B—H7B	117 (2)	H4D—C2D—H6D	109.5
H6B—N7B—H7B	118 (3)	H5D—C2D—H6D	109.5
C7B—N8B—C8AB	117.6 (2)	C2D'—S1D'—O1D'	117 (4)
N1B—C8AB—N8B	117.7 (2)	C2D'—S1D'—C1D'	80 (3)
N1B—C8AB—C4AB	122.0 (2)	O1D'—S1D'—C1D'	105 (4)
N8B—C8AB—C4AB	120.3 (2)	S1D'—C1D'—H1D'	109.5
C10B—C9B—C14B	118.4 (3)	S1D'—C1D'—H2D'	109.5
C10B—C9B—C6B	123.5 (3)	H1D'—C1D'—H2D'	109.5
C14B—C9B—C6B	118.1 (2)	S1D'—C1D'—H3D'	109.5
C9B—C10B—C11B	120.8 (3)	H1D'—C1D'—H3D'	109.5
C9B—C10B—H10B	119.8 (17)	H2D'—C1D'—H3D'	109.5
C11B—C10B—H10B	119.5 (18)	S1D'—C2D'—H4D'	109.5
C12B—C11B—C10B	120.0 (3)	S1D'—C2D'—H5D'	109.5
C12B—C11B—H11B	125 (2)	H4D'—C2D'—H5D'	109.5
C10B—C11B—H11B	115 (2)	S1D'—C2D'—H6D'	109.5
C13B—C12B—C11B	119.8 (3)	H4D'—C2D'—H6D'	109.5
C13B—C12B—H12B	121 (2)	H5D'—C2D'—H6D'	109.5
C11B—C12B—H12B	119 (2)
C8AA—N1A—C2A—N2A	−177.8 (2)	C4B—C4AB—N5B—C6B	−177.4 (2)
C8AA—N1A—C2A—N3A	2.9 (4)	C4AB—N5B—C6B—C7B	1.9 (4)
N2A—C2A—N3A—C4A	179.1 (2)	C4AB—N5B—C6B—C9B	177.3 (2)
N1A—C2A—N3A—C4A	−1.6 (4)	N5B—C6B—C7B—N8B	−4.4 (4)
C2A—N3A—C4A—N4A	178.4 (2)	C9B—C6B—C7B—N8B	−179.6 (2)
C2A—N3A—C4A—C4AA	−0.8 (4)	N5B—C6B—C7B—N7B	172.0 (2)
N4A—C4A—C4AA—N5A	0.2 (4)	C9B—C6B—C7B—N7B	−3.2 (4)
N3A—C4A—C4AA—N5A	179.4 (2)	N7B—C7B—N8B—C8AB	−174.1 (2)
N4A—C4A—C4AA—C8AA	−177.4 (3)	C6B—C7B—N8B—C8AB	2.4 (4)
N3A—C4A—C4AA—C8AA	1.8 (4)	C2B—N1B—C8AB—N8B	−176.1 (2)
C8AA—C4AA—N5A—C6A	0.1 (4)	C2B—N1B—C8AB—C4AB	2.4 (4)
C4A—C4AA—N5A—C6A	−177.4 (2)	C7B—N8B—C8AB—N1B	−179.8 (2)
C4AA—N5A—C6A—C7A	−2.3 (4)	C7B—N8B—C8AB—C4AB	1.7 (4)
C4AA—N5A—C6A—C9A	177.3 (2)	N5B—C4AB—C8AB—N1B	177.3 (2)
N5A—C6A—C7A—N7A	−176.9 (3)	C4B—C4AB—C8AB—N1B	−3.0 (4)
C9A—C6A—C7A—N7A	3.5 (4)	N5B—C4AB—C8AB—N8B	−4.2 (4)
N5A—C6A—C7A—N8A	3.0 (4)	C4B—C4AB—C8AB—N8B	175.4 (2)
C9A—C6A—C7A—N8A	−176.6 (3)	N5B—C6B—C9B—C10B	139.9 (3)
N7A—C7A—N8A—C8AA	178.7 (3)	C7B—C6B—C9B—C10B	−44.8 (4)
C6A—C7A—N8A—C8AA	−1.2 (4)	N5B—C6B—C9B—C14B	−39.4 (4)
C7A—N8A—C8AA—N1A	178.8 (2)	C7B—C6B—C9B—C14B	135.9 (3)
C7A—N8A—C8AA—C4AA	−1.0 (4)	C14B—C9B—C10B—C11B	−0.7 (4)
C2A—N1A—C8AA—N8A	178.5 (2)	C6B—C9B—C10B—C11B	−180.0 (3)
C2A—N1A—C8AA—C4AA	−1.7 (4)	C9B—C10B—C11B—C12B	−0.2 (5)
N5A—C4AA—C8AA—N8A	1.7 (4)	C10B—C11B—C12B—C13B	1.2 (5)
C4A—C4AA—C8AA—N8A	179.2 (2)	C11B—C12B—C13B—C14B	−1.3 (5)
N5A—C4AA—C8AA—N1A	−178.1 (2)	C12B—C13B—C14B—C9B	0.3 (5)
C4A—C4AA—C8AA—N1A	−0.5 (4)	C10B—C9B—C14B—C13B	0.6 (4)
N5A—C6A—C9A—C10A	51.6 (4)	C6B—C9B—C14B—C13B	180.0 (3)
C7A—C6A—C9A—C10A	−128.8 (3)	O1C—C1C—C2C—C3C	148.3 (5)
N5A—C6A—C9A—C14A	−123.8 (3)	O2C—C1C—C2C—C3C	−33.1 (6)
C7A—C6A—C9A—C14A	55.8 (4)	O1C—C1C—C2C—C4C	−78.6 (4)
C14A—C9A—C10A—C11A	0.1 (5)	O2C—C1C—C2C—C4C	99.9 (4)
C6A—C9A—C10A—C11A	−175.5 (3)	C3C—C2C—C4C—C9C	−120.4 (5)
C9A—C10A—C11A—C12A	1.3 (5)	C1C—C2C—C4C—C9C	106.0 (4)
C10A—C11A—C12A—C13A	−1.0 (6)	C3C—C2C—C4C—C5C	61.7 (6)
C11A—C12A—C13A—C14A	−0.7 (6)	C1C—C2C—C4C—C5C	−72.0 (5)
C12A—C13A—C14A—C9A	2.1 (6)	C9C—C4C—C5C—C6C	3.2 (6)
C10A—C9A—C14A—C13A	−1.8 (5)	C2C—C4C—C5C—C6C	−178.7 (4)
C6A—C9A—C14A—C13A	173.7 (3)	C4C—C5C—C6C—C7C	0.1 (8)
C8AB—N1B—C2B—N2B	179.9 (3)	C5C—C6C—C7C—C8C	−3.2 (7)
C8AB—N1B—C2B—N3B	0.6 (4)	C5C—C6C—C7C—C10C	176.9 (4)
N1B—C2B—N3B—C4B	−2.7 (4)	C6C—C7C—C8C—C9C	2.9 (6)
N2B—C2B—N3B—C4B	178.0 (3)	C10C—C7C—C8C—C9C	−177.1 (4)
C2B—N3B—C4B—N4B	−178.4 (3)	C5C—C4C—C9C—C8C	−3.5 (6)
C2B—N3B—C4B—C4AB	1.8 (4)	C2C—C4C—C9C—C8C	178.4 (3)
N4B—C4B—C4AB—N5B	0.7 (4)	C7C—C8C—C9C—C4C	0.5 (6)
N3B—C4B—C4AB—N5B	−179.5 (2)	C6C—C7C—C10C—C11C	−87.1 (6)
N4B—C4B—C4AB—C8AB	−179.0 (3)	C8C—C7C—C10C—C11C	93.0 (6)
N3B—C4B—C4AB—C8AB	0.8 (4)	C7C—C10C—C11C—C13C	−49.4 (8)
C8AB—C4AB—N5B—C6B	2.2 (4)	C7C—C10C—C11C—C12C	174.4 (5)