research papers\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

IUCrJ
Volume 5| Part 3| May 2018| Pages 309-324
ISSN: 2052-2525

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

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aDepartment of Chemistry, University of Cambridge, Lensfield Road, Cambridge, Cambridgeshire CB2 1EW, England, and bStrathclyde Institute of Pharmacy and Biomedical Sciences (SIPBS), University of Strathclyde, 161 Cathedral Street, Glasgow G4 0RE, Scotland
*Correspondence e-mail: amitdelori@gmail.com, dh536@cam.ac.uk

Edited by L. R. MacGillivray, University of Iowa, USA (Received 11 December 2017; accepted 26 February 2018; online 6 April 2018)

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 ΔpKa rule as proposed by Cruz-Cabeza [(2012[Cruz-Cabeza, A. J. (2012). CrystEngComm, 14, 6362-6365.]). 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[Dittert, L. W., Higuchi, T. & Reese, D. R. (1964). J. Pharm. Sci. 53, 1325-1328.]), and is therefore an excellent candidate for a cocrystal or salt screen (Thakuria et al., 2013[Thakuria, R., Delori, A., Jones, W., Lipert, M. P., Roy, L. & Rodríguez-Hornedo, N. (2013). Int. J. Pharm. 453, 101-125.]; Duggirala et al., 2016[Duggirala, N. K., Perry, M. L., Almarsson, O., Örn, & Zaworotko, M. J. (2016). Chem. Commun. 52, 640-655.]). A recent study (Ma et al., 2013[Ma, W. J., Chen, J. M., Jiang, L., Yao, J. & Lu, T. B. (2013). Mol. Pharm. 10, 4698-4705.]) 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[Bhatt, P. M., Azim, Y., Thakur, T. S. & Desiraju, G. R. (2009). Cryst. Growth Des. 9, 951-957.]), Generally Regarded As Safe (GRAS) molecules (Delori et al., 2008[Delori, A., Suresh, E. & Pedireddi, V. R. (2008). Chem. Eur. J. 14, 6967-6977.]; Aitipamula et al., 2014[Aitipamula, S., Chow, P. S. & Tan, R. B. H. (2014). CrystEngComm, 16, 3451-3465.]; Lu & Rohani, 2010[Lu, J. & Rohani, S. (2010). J. Pharm. Sci. 99, 4042-4047.]) and Active Pharmaceutical Ingredients (APIs) (Huang et al., 2014[Huang, Y. T., Zhang, B. W., Gao, Y., Zhang, J. J. & Shi, L. M. (2014). J. Pharm. Sci. 103, 2330-2337.]; Sowa et al., 2012[Sowa, M., Ślepokura, K. & Matczak-Jon, E. (2012). Acta Cryst. C68, 262-265.]; Báthori et al., 2011[Báthori, N. B., Lemmerer, A., Venter, G. A., Bourne, S. A. & Caira, M. R. (2011). Cryst. Growth Des. 11, 75-87.]; Delori, Galek et al., 2013[Delori, A., Galek, P. T. A., Pidcock, E., Patni, M. & Jones, W. (2013). CrystEngComm, 15, 2916-2928.]; Grobelny et al., 2011[Grobelny, P., Mukherjee, A. & Desiraju, G. R. (2011). CrystEngComm, 13, 4358-4364.]) also provides a means to improve the physicochemical properties of 1. For example, a recent study by Li et al. (2015[Li, A. Y., Xu, L. L., Chen, J. M. & Lu, T. B. (2015). Cryst. Growth Des. 15, 3785-3791.]) 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, S., Vangala, V. R., Chow, P. S. & Tan, R. B. H. (2012). Cryst. Growth Des. 12, 5858-5863.]; Aitipamula, Wong et al., 2012[Aitipamula, S., Wong, A. B. H., Chow, P. S. & Tan, R. B. H. (2012). CrystEngComm, 14, 8515-8524.]; Sanphui et al., 2011[Sanphui, P., Goud, N. R., Khandavilli, U. B. R., Bhanoth, S. & Nangia, A. (2011). Chem. Commun. 47, 5013-5015.]) but have also been used in altering various other physical properties, such as colour (Stahl & Wermuth, 2008[Stahl, P. H. & Wermuth, C. G. (2008). In Handbook of Pharmaceutical Salts: Properties, Selection, and Use. Weinheim: Wiley.]; Pallipurath et al., 2015[Pallipurath, A., Skelton, J. M., Delori, A., Duffy, C., Erxleben, A. & Jones, W. (2015). CrystEngComm, 17, 7684-7692.]; Delori et al., 2016[Delori, A., Urquhart, A. J. & Oswald, I. D. H. (2016). CrystEngComm, 18, 5360-5364.]), melting point (Friščić & Jones, 2010[Friščić, T. & Jones, W. (2010). J. Pharm. Pharmacol. 62, 1547-1559.]), stability to humidity (Trask et al., 2005[Trask, A. V., Motherwell, W. D. S. & Jones, W. (2005). Cryst. Growth Des. 5, 1013-1021.], 2006[Trask, A. V., Motherwell, W. D. S. & Jones, W. (2006). Int. J. Pharm. 320, 114-123.]), tableting properties (Bučar et al., 2015[Bučar, D. K., Elliott, J. A., Eddleston, M. D., Cockcroft, J. K. & Jones, W. (2015). Angew. Chem. 127, 251-255.]) fluorescence (Bučar et al., 2013[Bučar, D. K., Filip, S., Arhangelskis, M., Lloyd, G. O. & Jones, W. (2013). CrystEngComm, 15, 6289-6291.]; Yan et al., 2013[Yan, D. P., Patel, B., Delori, A., Jones, W. & Duan, X. (2013). Cryst. Growth Des. 13, 333-340.]) and polymorphic conversion (Delori et al., 2014[Delori, A., Maclure, P., Bhardwaj, R. M., Johnston, A., Florence, A. J., Sutcliffe, O. B. & Oswald, I. D. H. (2014). CrystEngComm, 16, 5827-5831.]).

As shown in Fig. 1[link], 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]
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[Bhatt, P. M., Azim, Y., Thakur, T. S. & Desiraju, G. R. (2009). Cryst. Growth Des. 9, 951-957.]; Delori et al., 2012[Delori, A., Galek, P. T. A., Pidcock, E. & Jones, W. (2012). Chem. Eur. J. 18, 6835-6846.]; Delori, Galek et al., 2013[Delori, A., Galek, P. T. A., Pidcock, E., Patni, M. & Jones, W. (2013). CrystEngComm, 15, 2916-2928.]; Huang et al., 2014[Huang, Y. T., Zhang, B. W., Gao, Y., Zhang, J. J. & Shi, L. M. (2014). J. Pharm. Sci. 103, 2330-2337.]; Wood et al., 2014[Wood, P. A., Feeder, N., Furlow, M., Galek, P. T. A., Groom, C. R. & Pidcock, E. (2014). CrystEngComm, 16, 5839-5848.]) 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[Galek, P. T. A., Fábián, L., Motherwell, W. D. S., Allen, F. H. & Feeder, N. (2007). Acta Cryst. B63, 768-782.], 2010[Galek, P. T. A., Fábián, L. & Allen, F. H. (2010). CrystEngComm, 12, 2091-2099.]). 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[Fábián, L. (2009). Cryst. Growth Des. 9, 1436-1443.]). 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[Desiraju, G. R. (1995). Angew. Chem. Int. Ed. Engl. 34, 2311-2327.]; Varughese et al., 2010[Varughese, S., Azim, Y. & Desiraju, G. R. (2010). J. Pharm. Sci. 99, 3743-3753.]; Arhangelskis et al., 2012[Arhangelskis, M., Lloyd, G. O. & Jones, W. (2012). CrystEngComm, 14, 5203-5208.]). This approach relies on the interaction between complementary functional groups in the formation of hydrogen-bonded adducts (Etter, 1991[Etter, M. C. (1991). J. Phys. Chem. 95, 4601-4610.]; Etter & Reutzel, 1991[Etter, M. C. & Reutzel, S. M. (1991). J. Am. Chem. Soc. 113, 2586-2598.]; Etter et al., 1990[Etter, M. C., Urbanczyk-Lipkowska, Z., Zia-Ebrahimi, M. & Panunto, T. W. (1990). J. Am. Chem. Soc. 112, 8415-8426.]). 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[link]).

[Figure 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 ΔpKa rule was applied by Cheney, Shan et al. (2010[Cheney, M. L., Shan, N., Healey, E. R., Hanna, M., Wojtas, L., Zaworotko, M. J., Sava, V., Song, S. J. & Sanchez-Ramos, J. R. (2010). Cryst. Growth Des. 10, 394-405.]) and Cheney, Weyna et al. (2010[Cheney, M. L., Weyna, D. R., Shan, N., Hanna, M., Wojtas, L. & Zaworotko, M. J. (2010). Cryst. Growth Des. 10, 4401-4413.]). It is widely acknowledged (Childs et al., 2007[Childs, S. L., Stahly, G. P. & Park, A. (2007). Mol. Pharm. 4, 323-338.]) that if the calculated ΔpKa lies in the range 0–3 then prediction becomes unreliable. An improvement of this method has subsequently been proposed by Cruz-Cabeza (2012[Cruz-Cabeza, A. J. (2012). CrystEngComm, 14, 6362-6365.]) 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[Cruz-Cabeza, A. J. (2012). CrystEngComm, 14, 6362-6365.]) is explored in order to predict the outcome of a given adduct formation reaction where Pobs is the probability (%) of observing AB (cocrystal) and AB+ (salt).

[P_{\rm{obs}} (AB, \%) =-17{\Delta{\rm p}K_{\rm a}} + 72\,, {\rm for} -1\leq{\Delta{\rm p}K_{\rm a}}\leq 4]

[P_{\rm{obs}} (A^- B^+, \%) =17{\Delta{\rm p}K_{\rm a}} + 28\,, {\rm for} -1\leq{\Delta{\rm p}K_{\rm a}}\leq 4]

The Pobs 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 (ae) 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 1ag·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[Groom, C. R., Bruno, I. J., Lightfoot, M. P & Ward, S. C. (2016). Acta. Cryst. B72, 171-179.]) revealed two crystal structures of 1 with the refcodes FITZAJ (Schwalbe & Williams, 1987[Schwalbe, C. H. & Williams, G. J. B. (1987). Acta Cryst. C43, 1097-1100.]) and FITZAJ01 (Tutughamiarso & Bolte, 2007[Tutughamiarso, M. & Bolte, M. (2007). Private communication (refcode: FITZAJ01). CCDC, Cambridge, England.]). These crystal structures have fairly high R1 values [Fo > 3σ and I > 2σ(I) of 0.09 and 0.0739, respectively] so in our previous work (Hughes et al., 2017[Hughes, D. S., Delori, A., Rehman, A. & Jones, W. (2017). Chem. Cent. J. 11, 63-82.]), 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 1ag·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[Bruker (2007). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]), followed by an absorption correction using SADABS (Bruker, 2001[Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]). The structures for 1ag·DMSO were all solved using SIR92 (Altomare et al., 1993[Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardii, A. (1993). J. Appl. Cryst. 26, 343-350.]) and were refined using the least-squares methods employed in SHELXL2013 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]). 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[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]). All diagrams relating to the crystal structure of 1ag·DMSO were generated using the Mercury 3.9 module of the CSD Enterprise package (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]).

Table 1[link] contains selected crystallographic parameters for 1 and 1ag·DMSO. Table S3 (see supporting information) contains further crystallographic details relating to data collection and structure refinement for 1 and 1ag·DMSO. Table S4 contains details of the labelling scheme for 1 and 1ag·DMSO, Figs. S2–S9 show the asymmetric units for 1 and 1ag·DMSO and Tables S5–S12 contain details of the hydrogen bond schemes for 1 and 1ag·DMSO. The supplementary crystallographic data (CIF files) for 1ag·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 1ag·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+·C6H8O42−·2C2H6OS 2C12H12N7+·C7H10O42−·2C2H6OS 2C12H12N7+·C9H14O42−·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 [P \bar 1] [P \bar 1] P21/c [P \bar 1] [P \bar 1] P21/n P21/n [P \bar 1]
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−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 F2 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[Hughes, D. S., Delori, A., Rehman, A. & Jones, W. (2017). Chem. Cent. J. 11, 63-82.]).

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 1ag·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 1ag·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 ag existed as salt solvates (Grothe et al., 2016[Grothe, E., Meekes, H., Vlieg, E., ter Horst, J. H. & de Gelder, R. (2016). Cryst. Growth Des. 16, 3237-3243.]). 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 ΔpKa values (Hilal et al., 1995[Hilal, S. H., Karickhoff, S. W. & Carreira, L. A. (1995). Quant. Struct.-Act. Relat. 14, 348-355.]) are smallest, thereby providing support for the validity of the modified pKa rule of Cruz-Cabeza (2012[Cruz-Cabeza, A. J. (2012). CrystEngComm, 14, 6362-6365.]) in this case. Exceptions are known to the pKa rule, primarily because of the fact that pKa 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[Molčanov, K. & Kojić-Prodić, B. (2010). CrystEngComm, 12, 925-939.]).

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 ag 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 ag. 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[link]. If proton transfer occurs then, from the pKa 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[Hughes, D. S., Delori, A., Rehman, A. & Jones, W. (2017). Chem. Cent. J. 11, 63-82.]), 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[Desiraju, G. R. (1995). Angew. Chem. Int. Ed. Engl. 34, 2311-2327.]) 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 [P \bar 1] with two independent molecules in the asymmetric unit (Z = 4), as shown in Table 1[link]. 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. 3[link]a). The M3 motif joins two molecules in adjacent tapes through N—H⋯N hydrogen bonds involving the 7-amino group (see Fig. 3[link]b). 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]
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. 3[link]a for details).

Overlapping tapes of 1 (Fig. 3[link]b) 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. 3[link]c).

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 [P \bar 1] (see Table 1[link]). 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. 4[link]a for details).

[Figure 4]
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. 4[link]a). 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[link](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[link]). 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[link]). 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[link]). We note that in the crystal structure the cyclic networks are made by 1, b and solvent molecules (Fig. 5[link]), 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]
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[link] for details).

[Figure 6]
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 [P \bar 1] (see Table 1[link]); 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[link](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[link](b).

[Figure 7]
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[link]). Such host–guest assemblies are well known in the field of supramolecular chemistry (Bhatt et al., 2009[Bhatt, P. M., Azim, Y., Thakur, T. S. & Desiraju, G. R. (2009). Cryst. Growth Des. 9, 951-957.]; Galcera et al., 2012[Galcera, J., Friščić, T., Hejczyk, K. E., Fábián, L., Clarke, S. M., Day, G. M., Molins, E. & Jones, W. (2012). CrystEngComm, 14, 7898-7906.]).

[Figure 8]
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 [P \bar 1] space group (see Table 1[link]) 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. 9[link]a), as seen in 1b·DMSO (see Fig. 6[link]). As noted earlier, this tape is fundamentally different from the supramolecular tape found in 1c·DMSO (see Fig. 7[link]) since, in this case, motifs M3 and M4 are not involved in creating a trimer of 1 molecules.

[Figure 9]
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. 9[link]a). 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. 9[link]a). 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. 9[link]b).

A hydrogen-bonded sheet structure formed by the combination of host–guest networks is shown in Fig. 9[link](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[link](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[link]). 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[link](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. 10[link]b).

[Figure 10]
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[link](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[link]). 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 ABAB 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[link](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[link](a).

[Figure 11]
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[link](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. 12[link]a). 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[link](b).

[Figure 12]
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[link].

[Figure 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 [P \bar 1], as shown in Table 1[link]. 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 AABB dimers. These further link through M11 and M12 motifs to create an AABBAA zigzag crinkled tape of 1 molecules (Figs. 14[link] and 21[link]).

[Figure 14]
Figure 14
The crinkled tape of molecules of 1 observed in the crystal structure of 1g·DMSO.
[Figure 21]
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 af. However, in this case, the M7 motif is absent since molecules of 1 combine to form the M11 motif, as shown in Fig. 15[link]. 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[link] for details).

[Figure 15]
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. 16[link]a). 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. 16[link]b and highlighted in Fig. 16[link]c).

[Figure 16]
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 (1ag)

Overall, 14 different motifs have been observed in 1 and the reported adducts 1ag·DMSO (see Figs. 17[link] and 19). It is recognized that the standard graph-set notation Gda(n) introduced by Etter (1991[Etter, M. C. (1991). J. Phys. Chem. 95, 4601-4610.]) and described in Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]) 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]
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[link]). 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[link] 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]
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[link]).

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[link]).

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[link].

A CSD analysis undertaken by Delori, Suresh & Pedireddi (2013[Delori, A., Suresh, E. & Pedireddi, V. R. (2013). CrystEngComm, 15, 4811-4815.]) 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[link]). 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[link].

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 (ag) are shown in Fig. 19[link].

[Figure 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[link] 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]
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[link] and represented by the supramolecular R32(8) synthon S5 in Fig. 20[link] are formed through charge-assisted N+—H⋯Oand 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[link]) 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[link]) 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[link]) 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[Allen, F. H., Samuel Motherwell, W. D., Raithby, P. R., Shields, G. P. & Taylor, R. (1999). New J. Chem. 23, 25-34.]) 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[Delori, A., Galek, P. T. A., Pidcock, E., Patni, M. & Jones, W. (2013). CrystEngComm, 15, 2916-2928.]) 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[link]) 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[link].

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[link]. 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]
Figure 22
Summary of hydrogen-bond motifs found in this study. Green represents 11 interactions, blue represents 1–solvent interactions, red represents 1–coformer interactions and purple represents solvent–1–coformer interactions.

From Fig. 22[link] 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 11 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 11 motifs M11 and M12 that combine to form a unique dimer structure (TM23).

Furthermore, it can be seen from Fig. 22[link] 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 ΔpKa discussed earlier (see Fig. 2[link] for details). The CSD search outlined in §3.9.2[link] 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[Delori, A., Galek, P. T. A., Pidcock, E., Patni, M. & Jones, W. (2013). CrystEngComm, 15, 2916-2928.]) and the triazines (Bhatt et al., 2009[Bhatt, P. M., Azim, Y., Thakur, T. S. & Desiraju, G. R. (2009). Cryst. Growth Des. 9, 951-957.]) 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[Perumalla, S. R., Pedireddi, V. R. & Sun, C. C. (2013). Cryst. Growth Des. 13, 429-432.]) 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 pKa > 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 pKa value of 5.2 but can form the triamterenium ion with the stronger carb­oxy­lic acids in the pKa range 4.2–4.76.

5. Conclusions

The salt solvate adducts 1ag·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 ΔpKa rule proposed by Cruz-Cabeza (2012[Cruz-Cabeza, A. J. (2012). CrystEngComm, 14, 6362-6365.]). 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 1af·DMSO and M11 in 1g·DMSO. The present study and the CSD survey carried out by Delori, Suresh & Pedireddi (2013[Delori, A., Suresh, E. & Pedireddi, V. R. (2013). CrystEngComm, 15, 4811-4815.]) 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[link], resulting from the crystal engineering approach which emphasizes the identification of systematic patterns of hydrogen bonds from known crystal structures. Overall seven adducts (1ag. 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 top

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) top
Crystal data top
C12H12N7+·C2H6OS·C2H3O2Z = 4
Mr = 391.46F(000) = 824
Triclinic, P1Dx = 1.408 Mg m3
a = 10.8022 (2) ÅMo Kα radiation, λ = 0.7107 Å
b = 13.9084 (2) ÅCell parameters from 10617 reflections
c = 14.6076 (3) Åθ = 1.0–30.0°
α = 115.284 (1)°µ = 0.21 mm1
β = 109.088 (2)°T = 180 K
γ = 90.525 (1)°Block, colourless
V = 1846.64 (6) Å30.25 × 0.12 × 0.10 mm
Data collection top
Nonius Kappa CCD
diffractometer
10617 independent reflections
Radiation source: fine-focus sealed tube6401 reflections with I > 2σ(I)
None monochromatorRint = 0.042
Thin slice ω and φ scansθmax = 30.0°, θmin = 3.6°
Absorption correction: multi-scan
multi-scan from symmetry-related measurements Sortav (Blessing 1995)
h = 1514
Tmin = 0.901, Tmax = 0.999k = 1918
24626 measured reflectionsl = 1420
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Hydrogen site location: difference Fourier map
wR(F2) = 0.126All H-atom parameters refined
S = 0.94 w = 1/[σ2(Fo2) + (0.0695P)2]
where P = (Fo2 + 2Fc2)/3
10617 reflections(Δ/σ)max < 0.001
655 parametersΔρmax = 0.67 e Å3
0 restraintsΔρmin = 0.44 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
N1A0.17280 (11)0.57437 (11)0.35562 (10)0.0229 (3)
C2A0.05142 (13)0.59853 (13)0.31573 (12)0.0239 (3)
N2A0.04629 (14)0.67427 (12)0.28419 (12)0.0331 (3)
N3A0.06158 (11)0.54961 (11)0.30881 (10)0.0246 (3)
C4A0.05437 (13)0.47345 (12)0.34241 (12)0.0228 (3)
N4A0.16567 (12)0.42709 (12)0.33735 (12)0.0286 (3)
C4AA0.07019 (13)0.44160 (12)0.38249 (12)0.0217 (3)
N5A0.07477 (11)0.35713 (10)0.40616 (10)0.0228 (3)
C6A0.19142 (13)0.32920 (12)0.43795 (12)0.0219 (3)
C7A0.31158 (13)0.39361 (12)0.45524 (12)0.0228 (3)
N7A0.43140 (12)0.37284 (12)0.49680 (12)0.0295 (3)
N8A0.30584 (11)0.47503 (10)0.42881 (10)0.0230 (3)
C8AA0.18412 (13)0.49606 (12)0.38962 (12)0.0210 (3)
C9A0.19363 (13)0.22864 (12)0.45035 (12)0.0235 (3)
C10A0.13629 (16)0.21453 (15)0.51756 (14)0.0310 (4)
C11A0.12724 (17)0.11655 (16)0.52084 (16)0.0373 (4)
C12A0.17298 (16)0.03115 (15)0.45542 (15)0.0354 (4)
C13A0.23056 (16)0.04472 (15)0.38950 (14)0.0315 (4)
C14A0.24234 (15)0.14300 (14)0.38726 (13)0.0271 (3)
N1B0.33114 (12)0.43741 (10)0.16905 (10)0.0229 (3)
C2B0.45354 (13)0.42190 (12)0.22065 (12)0.0226 (3)
N2B0.45957 (14)0.34979 (12)0.25696 (12)0.0282 (3)
N3B0.56766 (11)0.47624 (11)0.23461 (10)0.0255 (3)
C4B0.56048 (14)0.54651 (13)0.19385 (13)0.0255 (3)
C4AB0.43474 (13)0.56628 (13)0.13775 (12)0.0234 (3)
N4B0.67234 (14)0.59768 (13)0.20525 (14)0.0373 (4)
N5B0.42955 (11)0.64195 (10)0.10210 (10)0.0236 (3)
C6B0.31226 (13)0.66138 (12)0.05765 (12)0.0221 (3)
C7B0.19169 (13)0.59773 (12)0.04065 (12)0.0224 (3)
N7B0.07306 (13)0.61269 (13)0.01150 (13)0.0328 (3)
N8B0.19716 (11)0.52335 (10)0.07690 (10)0.0237 (3)
C8AB0.31933 (13)0.51014 (12)0.12724 (12)0.0217 (3)
C9B0.30992 (13)0.75360 (13)0.03081 (12)0.0229 (3)
C10B0.34291 (17)0.74670 (17)0.05564 (15)0.0343 (4)
C11B0.35784 (19)0.83637 (19)0.07114 (19)0.0465 (5)
C12B0.34014 (17)0.93355 (17)0.00130 (17)0.0438 (5)
C13B0.30430 (17)0.94238 (16)0.08426 (16)0.0397 (4)
C14B0.28863 (16)0.85209 (14)0.09990 (14)0.0313 (4)
C1C0.3050 (2)0.1919 (2)0.9589 (2)0.0527 (6)
O1C0.17699 (11)0.23199 (11)0.79740 (10)0.0432 (3)
S1C0.16603 (4)0.24236 (4)0.90154 (4)0.03472 (12)
C2C0.0360 (3)0.1365 (2)0.8598 (2)0.0588 (6)
C1D0.5869 (3)0.1097 (2)0.3693 (3)0.0630 (7)
O1D0.70351 (11)0.27236 (11)0.36551 (11)0.0434 (3)
S1D0.73929 (4)0.19095 (4)0.40657 (4)0.03484 (12)
C2D0.8063 (3)0.0960 (2)0.3155 (2)0.0613 (7)
C1E0.62951 (14)0.23148 (13)0.66048 (12)0.0246 (3)
O1E0.61539 (10)0.29807 (10)0.62197 (10)0.0361 (3)
C2E0.50478 (17)0.16465 (17)0.64250 (17)0.0346 (4)
O2E0.73846 (10)0.21589 (9)0.71096 (9)0.0337 (3)
C1F0.13081 (14)0.23043 (13)0.15957 (12)0.0258 (3)
O1F0.11401 (10)0.30967 (10)0.13920 (10)0.0346 (3)
C2F0.00873 (18)0.16139 (18)0.14287 (17)0.0386 (4)
O2F0.24120 (10)0.20366 (10)0.19082 (10)0.0384 (3)
H1XA0.2443 (17)0.6137 (15)0.3609 (14)0.032 (5)*
H2A0.1179 (19)0.7055 (15)0.2861 (14)0.037 (5)*
H3A0.028 (2)0.6919 (16)0.2629 (15)0.044 (5)*
H4A0.2396 (18)0.4479 (14)0.3118 (13)0.031 (5)*
H5A0.1666 (16)0.3788 (15)0.3581 (14)0.035 (5)*
H6A0.4382 (15)0.3327 (14)0.5265 (13)0.023 (4)*
H7A0.5026 (19)0.4205 (17)0.5128 (15)0.046 (5)*
H10A0.1006 (16)0.2704 (14)0.5572 (13)0.031 (5)*
H11A0.0823 (18)0.1080 (16)0.5604 (15)0.043 (5)*
H12A0.1665 (17)0.0335 (16)0.4571 (14)0.040 (5)*
H13A0.2603 (16)0.0073 (15)0.3526 (14)0.029 (5)*
H14A0.2795 (17)0.1504 (15)0.3402 (14)0.038 (5)*
H1XB0.2609 (18)0.3973 (16)0.1623 (14)0.038 (5)*
H2B0.3823 (18)0.3088 (15)0.2391 (13)0.030 (4)*
H3B0.5300 (17)0.3387 (14)0.2880 (13)0.027 (5)*
H4B0.7444 (19)0.5872 (15)0.2356 (14)0.032 (5)*
H5B0.6700 (18)0.6485 (17)0.1863 (16)0.048 (6)*
H6B0.0681 (16)0.6547 (15)0.0380 (13)0.027 (5)*
H7B0.002 (2)0.5691 (17)0.0295 (16)0.047 (6)*
H10B0.3529 (18)0.6834 (16)0.0995 (15)0.044 (6)*
H11B0.374 (2)0.8251 (18)0.1330 (18)0.063 (7)*
H12B0.3511 (18)0.9934 (17)0.0114 (15)0.045 (5)*
H13B0.2904 (19)1.0071 (18)0.1300 (16)0.052 (6)*
H14B0.2654 (18)0.8558 (16)0.1546 (15)0.043 (5)*
H1C0.380 (2)0.242 (2)0.9726 (19)0.077 (8)*
H2C0.3113 (17)0.1280 (17)0.9066 (16)0.039 (5)*
H3C0.301 (2)0.191 (2)1.026 (2)0.077 (7)*
H4C0.047 (4)0.144 (3)0.821 (3)0.134 (14)*
H5C0.029 (3)0.136 (2)0.919 (2)0.094 (9)*
H6C0.061 (3)0.072 (3)0.818 (3)0.113 (12)*
H1D0.530 (4)0.157 (4)0.404 (3)0.174 (18)*
H2D0.605 (3)0.051 (3)0.381 (3)0.119 (12)*
H3D0.547 (3)0.091 (2)0.294 (2)0.096 (10)*
H4D0.894 (3)0.134 (2)0.321 (2)0.115 (11)*
H5D0.742 (3)0.067 (2)0.242 (2)0.086 (8)*
H6D0.820 (2)0.039 (2)0.3360 (19)0.072 (7)*
H1E0.517 (2)0.1496 (19)0.7051 (19)0.073 (7)*
H2E0.481 (2)0.092 (2)0.5764 (18)0.063 (7)*
H3E0.431 (2)0.1961 (19)0.6255 (18)0.068 (7)*
H1F0.029 (3)0.096 (3)0.068 (3)0.121 (11)*
H2F0.061 (3)0.192 (2)0.135 (2)0.105 (10)*
H3F0.028 (2)0.131 (2)0.189 (2)0.085 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.0159 (6)0.0249 (7)0.0332 (7)0.0045 (5)0.0073 (5)0.0190 (6)
C2A0.0196 (7)0.0262 (9)0.0287 (8)0.0051 (6)0.0073 (6)0.0161 (7)
N2A0.0192 (7)0.0395 (9)0.0535 (9)0.0084 (6)0.0102 (6)0.0348 (8)
N3A0.0171 (6)0.0291 (8)0.0339 (7)0.0062 (5)0.0079 (5)0.0209 (6)
C4A0.0177 (7)0.0239 (8)0.0270 (8)0.0046 (6)0.0059 (6)0.0135 (7)
N4A0.0167 (6)0.0333 (8)0.0459 (9)0.0062 (5)0.0082 (6)0.0292 (7)
C4AA0.0188 (7)0.0214 (8)0.0274 (8)0.0043 (5)0.0071 (6)0.0143 (7)
N5A0.0187 (6)0.0242 (7)0.0272 (7)0.0044 (5)0.0067 (5)0.0144 (6)
C6A0.0192 (7)0.0226 (8)0.0257 (7)0.0043 (6)0.0068 (6)0.0136 (7)
C7A0.0181 (7)0.0235 (8)0.0273 (8)0.0046 (6)0.0063 (6)0.0134 (7)
N7A0.0180 (7)0.0310 (8)0.0477 (9)0.0051 (6)0.0069 (6)0.0289 (7)
N8A0.0168 (6)0.0239 (7)0.0310 (7)0.0043 (5)0.0071 (5)0.0161 (6)
C8AA0.0182 (7)0.0211 (8)0.0246 (7)0.0055 (5)0.0065 (5)0.0121 (6)
C9A0.0168 (7)0.0237 (8)0.0291 (8)0.0026 (6)0.0033 (6)0.0149 (7)
C10A0.0286 (8)0.0303 (10)0.0425 (10)0.0091 (7)0.0168 (7)0.0210 (8)
C11A0.0359 (9)0.0386 (11)0.0513 (11)0.0054 (8)0.0198 (8)0.0297 (10)
C12A0.0319 (9)0.0273 (10)0.0469 (11)0.0007 (7)0.0040 (7)0.0246 (9)
C13A0.0324 (9)0.0231 (9)0.0326 (9)0.0081 (7)0.0054 (7)0.0117 (8)
C14A0.0251 (8)0.0283 (9)0.0297 (8)0.0061 (6)0.0076 (6)0.0166 (7)
N1B0.0163 (6)0.0231 (7)0.0329 (7)0.0035 (5)0.0069 (5)0.0173 (6)
C2B0.0200 (7)0.0222 (8)0.0272 (8)0.0058 (6)0.0083 (6)0.0128 (7)
N2B0.0171 (7)0.0340 (8)0.0410 (8)0.0071 (6)0.0069 (6)0.0264 (7)
N3B0.0171 (6)0.0284 (8)0.0352 (7)0.0057 (5)0.0072 (5)0.0199 (6)
C4B0.0192 (7)0.0265 (9)0.0338 (8)0.0047 (6)0.0077 (6)0.0179 (7)
C4AB0.0178 (7)0.0251 (8)0.0310 (8)0.0052 (6)0.0073 (6)0.0173 (7)
N4B0.0164 (7)0.0448 (10)0.0647 (11)0.0056 (6)0.0068 (6)0.0430 (9)
N5B0.0186 (6)0.0242 (7)0.0302 (7)0.0042 (5)0.0071 (5)0.0159 (6)
C6B0.0190 (7)0.0228 (8)0.0255 (7)0.0038 (5)0.0067 (6)0.0129 (7)
C7B0.0187 (7)0.0207 (8)0.0277 (8)0.0047 (5)0.0064 (6)0.0124 (7)
N7B0.0181 (7)0.0344 (9)0.0517 (9)0.0028 (6)0.0030 (6)0.0318 (8)
N8B0.0175 (6)0.0217 (7)0.0327 (7)0.0039 (5)0.0059 (5)0.0155 (6)
C8AB0.0190 (7)0.0201 (8)0.0262 (8)0.0036 (5)0.0061 (6)0.0122 (6)
C9B0.0146 (7)0.0258 (8)0.0292 (8)0.0024 (5)0.0030 (5)0.0169 (7)
C10B0.0362 (9)0.0403 (12)0.0410 (10)0.0185 (8)0.0203 (8)0.0264 (9)
C11B0.0443 (11)0.0681 (16)0.0625 (13)0.0231 (10)0.0306 (10)0.0523 (13)
C12B0.0313 (9)0.0443 (13)0.0687 (14)0.0020 (8)0.0085 (9)0.0445 (12)
C13B0.0377 (10)0.0236 (10)0.0449 (11)0.0041 (7)0.0004 (8)0.0156 (9)
C14B0.0354 (9)0.0296 (10)0.0280 (9)0.0080 (7)0.0078 (7)0.0150 (8)
C1C0.0625 (15)0.0538 (15)0.0415 (12)0.0268 (12)0.0133 (10)0.0253 (12)
O1C0.0324 (6)0.0601 (9)0.0575 (8)0.0117 (6)0.0153 (6)0.0454 (8)
S1C0.0317 (2)0.0313 (3)0.0405 (2)0.00437 (17)0.00853 (17)0.0193 (2)
C2C0.0647 (16)0.0565 (17)0.0508 (14)0.0176 (12)0.0254 (12)0.0181 (13)
C1D0.0577 (14)0.0547 (17)0.0780 (19)0.0127 (12)0.0177 (13)0.0371 (15)
O1D0.0384 (7)0.0419 (8)0.0659 (9)0.0097 (6)0.0200 (6)0.0378 (7)
S1D0.0369 (2)0.0320 (3)0.0365 (2)0.00482 (18)0.00971 (18)0.0192 (2)
C2D0.0721 (17)0.0645 (17)0.0529 (14)0.0358 (14)0.0262 (12)0.0289 (13)
C1E0.0242 (7)0.0229 (8)0.0273 (8)0.0032 (6)0.0083 (6)0.0127 (7)
O1E0.0242 (6)0.0413 (8)0.0548 (8)0.0048 (5)0.0079 (5)0.0373 (7)
C2E0.0270 (9)0.0362 (11)0.0413 (10)0.0026 (7)0.0050 (7)0.0240 (9)
O2E0.0244 (6)0.0375 (7)0.0483 (7)0.0059 (5)0.0080 (5)0.0314 (6)
C1F0.0258 (8)0.0274 (9)0.0248 (8)0.0001 (6)0.0060 (6)0.0149 (7)
O1F0.0233 (5)0.0395 (7)0.0494 (7)0.0042 (5)0.0069 (5)0.0323 (6)
C2F0.0276 (9)0.0445 (12)0.0457 (11)0.0049 (8)0.0032 (8)0.0299 (10)
O2F0.0260 (6)0.0387 (8)0.0601 (8)0.0066 (5)0.0119 (5)0.0336 (7)
Geometric parameters (Å, º) top
N1A—C2A1.3591 (18)C6B—C7B1.456 (2)
N1A—C8AA1.3684 (18)C6B—C9B1.491 (2)
N1A—H1XA0.904 (18)C7B—N7B1.3294 (18)
C2A—N2A1.3130 (19)C7B—N8B1.3426 (18)
C2A—N3A1.3448 (18)N7B—H6B0.821 (18)
N2A—H2A0.870 (19)N7B—H7B0.86 (2)
N2A—H3A0.84 (2)N8B—C8AB1.3421 (17)
N3A—C4A1.3378 (18)C9B—C10B1.387 (2)
C4A—N4A1.3243 (19)C9B—C14B1.387 (2)
C4A—C4AA1.4376 (19)C10B—C11B1.376 (3)
N4A—H4A0.873 (18)C10B—H10B0.87 (2)
N4A—H5A0.848 (19)C11B—C12B1.363 (3)
C4AA—N5A1.3561 (18)C11B—H11B0.93 (2)
C4AA—C8AA1.3896 (19)C12B—C13B1.383 (3)
N5A—C6A1.3171 (17)C12B—H12B0.92 (2)
C6A—C7A1.457 (2)C13B—C14B1.387 (2)
C6A—C9A1.484 (2)C13B—H13B0.91 (2)
C7A—N7A1.3304 (18)C14B—H14B0.895 (18)
C7A—N8A1.3394 (18)C1C—S1C1.773 (2)
N7A—H6A0.832 (17)C1C—H1C0.97 (3)
N7A—H7A0.91 (2)C1C—H2C0.91 (2)
N8A—C8AA1.3416 (17)C1C—H3C1.01 (2)
C9A—C14A1.391 (2)O1C—S1C1.5098 (13)
C9A—C10A1.395 (2)S1C—C2C1.774 (2)
C10A—C11A1.388 (2)C2C—H4C0.93 (4)
C10A—H10A0.924 (17)C2C—H5C0.90 (3)
C11A—C12A1.385 (3)C2C—H6C0.95 (3)
C11A—H11A0.909 (19)C1D—S1D1.771 (2)
C12A—C13A1.376 (3)C1D—H1D0.99 (4)
C12A—H12A0.914 (19)C1D—H2D0.91 (3)
C13A—C14A1.387 (2)C1D—H3D0.95 (3)
C13A—H13A0.838 (18)O1D—S1D1.4925 (12)
C14A—H14A0.941 (17)S1D—C2D1.783 (2)
N1B—C2B1.3620 (18)C2D—H4D1.05 (3)
N1B—C8AB1.3753 (18)C2D—H5D0.97 (3)
N1B—H1XB0.891 (19)C2D—H6D0.96 (3)
C2B—N2B1.3131 (19)C1E—O2E1.2447 (17)
C2B—N3B1.3489 (18)C1E—O1E1.2606 (18)
N2B—H2B0.901 (18)C1E—C2E1.512 (2)
N2B—H3B0.803 (17)C2E—H1E0.99 (2)
N3B—C4B1.3357 (19)C2E—H2E1.01 (2)
C4B—N4B1.3213 (19)C2E—H3E0.93 (2)
C4B—C4AB1.4364 (19)C1F—O2F1.2515 (18)
C4AB—N5B1.3535 (18)C1F—O1F1.2588 (18)
C4AB—C8AB1.3937 (19)C1F—C2F1.512 (2)
N4B—H4B0.809 (19)C2F—H1F1.02 (3)
N4B—H5B0.86 (2)C2F—H2F0.87 (3)
N5B—C6B1.3108 (17)C2F—H3F0.91 (3)
C2A—N1A—C8AA120.19 (12)N7B—C7B—C6B120.12 (13)
C2A—N1A—H1XA117.3 (11)N8B—C7B—C6B121.31 (12)
C8AA—N1A—H1XA122.5 (11)C7B—N7B—H6B119.7 (11)
N2A—C2A—N3A119.34 (13)C7B—N7B—H7B120.0 (13)
N2A—C2A—N1A117.65 (13)H6B—N7B—H7B119.0 (17)
N3A—C2A—N1A123.00 (13)C8AB—N8B—C7B116.14 (12)
C2A—N2A—H2A120.8 (12)N8B—C8AB—N1B118.73 (12)
C2A—N2A—H3A117.9 (13)N8B—C8AB—C4AB122.61 (13)
H2A—N2A—H3A121.4 (18)N1B—C8AB—C4AB118.66 (12)
C4A—N3A—C2A118.56 (11)C10B—C9B—C14B118.74 (15)
N4A—C4A—N3A118.25 (12)C10B—C9B—C6B121.17 (15)
N4A—C4A—C4AA120.36 (13)C14B—C9B—C6B119.72 (14)
N3A—C4A—C4AA121.39 (12)C11B—C10B—C9B120.77 (19)
C4A—N4A—H4A117.9 (11)C11B—C10B—H10B122.0 (13)
C4A—N4A—H5A122.1 (11)C9B—C10B—H10B117.2 (13)
H4A—N4A—H5A120.0 (16)C12B—C11B—C10B120.18 (18)
N5A—C4AA—C8AA121.35 (12)C12B—C11B—H11B123.5 (14)
N5A—C4AA—C4A120.92 (12)C10B—C11B—H11B116.2 (14)
C8AA—C4AA—C4A117.61 (13)C11B—C12B—C13B120.33 (17)
C6A—N5A—C4AA117.82 (12)C11B—C12B—H12B120.0 (12)
N5A—C6A—C7A120.09 (13)C13B—C12B—H12B119.7 (12)
N5A—C6A—C9A117.51 (12)C12B—C13B—C14B119.65 (19)
C7A—C6A—C9A122.35 (12)C12B—C13B—H13B120.4 (13)
N7A—C7A—N8A117.43 (13)C14B—C13B—H13B120.0 (13)
N7A—C7A—C6A121.12 (13)C13B—C14B—C9B120.29 (17)
N8A—C7A—C6A121.45 (12)C13B—C14B—H14B121.3 (13)
C7A—N7A—H6A118.4 (11)C9B—C14B—H14B118.4 (13)
C7A—N7A—H7A116.8 (12)S1C—C1C—H1C103.0 (15)
H6A—N7A—H7A121.1 (16)S1C—C1C—H2C109.7 (11)
C7A—N8A—C8AA116.27 (12)H1C—C1C—H2C103.6 (19)
N8A—C8AA—N1A118.26 (12)S1C—C1C—H3C109.7 (13)
N8A—C8AA—C4AA122.54 (13)H1C—C1C—H3C114 (2)
N1A—C8AA—C4AA119.20 (12)H2C—C1C—H3C116.2 (18)
C14A—C9A—C10A118.84 (15)O1C—S1C—C1C104.76 (10)
C14A—C9A—C6A120.11 (14)O1C—S1C—C2C105.07 (10)
C10A—C9A—C6A120.80 (14)C1C—S1C—C2C100.02 (15)
C11A—C10A—C9A120.55 (17)S1C—C2C—H4C114 (2)
C11A—C10A—H10A120.6 (11)S1C—C2C—H5C109.0 (19)
C9A—C10A—H10A118.8 (10)H4C—C2C—H5C105 (3)
C12A—C11A—C10A119.94 (17)S1C—C2C—H6C105.8 (19)
C12A—C11A—H11A121.4 (13)H4C—C2C—H6C111 (3)
C10A—C11A—H11A118.2 (12)H5C—C2C—H6C111 (3)
C13A—C12A—C11A119.81 (17)S1D—C1D—H1D108 (2)
C13A—C12A—H12A120.1 (11)S1D—C1D—H2D108 (2)
C11A—C12A—H12A120.0 (11)H1D—C1D—H2D120 (3)
C12A—C13A—C14A120.62 (18)S1D—C1D—H3D101.4 (17)
C12A—C13A—H13A118.2 (12)H1D—C1D—H3D105 (3)
C14A—C13A—H13A121.2 (12)H2D—C1D—H3D112 (3)
C13A—C14A—C9A120.20 (16)O1D—S1D—C1D105.84 (11)
C13A—C14A—H14A119.7 (11)O1D—S1D—C2D105.48 (10)
C9A—C14A—H14A120.1 (11)C1D—S1D—C2D99.52 (16)
C2B—N1B—C8AB120.34 (12)S1D—C2D—H4D109.8 (17)
C2B—N1B—H1XB117.0 (11)S1D—C2D—H5D109.1 (15)
C8AB—N1B—H1XB122.6 (11)H4D—C2D—H5D110 (2)
N2B—C2B—N3B119.07 (12)S1D—C2D—H6D106.2 (14)
N2B—C2B—N1B118.05 (13)H4D—C2D—H6D113 (2)
N3B—C2B—N1B122.87 (13)H5D—C2D—H6D109 (2)
C2B—N2B—H2B117.1 (11)O2E—C1E—O1E124.82 (14)
C2B—N2B—H3B120.8 (12)O2E—C1E—C2E117.75 (14)
H2B—N2B—H3B121.7 (16)O1E—C1E—C2E117.43 (13)
C4B—N3B—C2B118.64 (11)C1E—C2E—H1E110.8 (13)
N4B—C4B—N3B118.55 (13)C1E—C2E—H2E112.2 (12)
N4B—C4B—C4AB119.99 (14)H1E—C2E—H2E106.0 (18)
N3B—C4B—C4AB121.46 (13)C1E—C2E—H3E111.3 (14)
N5B—C4AB—C8AB121.31 (12)H1E—C2E—H3E113.5 (18)
N5B—C4AB—C4B120.57 (12)H2E—C2E—H3E102.8 (18)
C8AB—C4AB—C4B118.01 (13)O2F—C1F—O1F124.59 (14)
C4B—N4B—H4B121.9 (13)O2F—C1F—C2F117.71 (14)
C4B—N4B—H5B119.7 (13)O1F—C1F—C2F117.69 (14)
H4B—N4B—H5B118.0 (18)C1F—C2F—H1F114.0 (17)
C6B—N5B—C4AB117.90 (12)C1F—C2F—H2F111.9 (19)
N5B—C6B—C7B120.50 (13)H1F—C2F—H2F96 (2)
N5B—C6B—C9B116.81 (12)C1F—C2F—H3F111.3 (16)
C7B—C6B—C9B122.64 (12)H1F—C2F—H3F103 (2)
N7B—C7B—N8B118.57 (13)H2F—C2F—H3F120 (2)
C8AA—N1A—C2A—N2A179.95 (14)C8AB—N1B—C2B—N2B178.46 (14)
C8AA—N1A—C2A—N3A1.0 (2)C8AB—N1B—C2B—N3B0.7 (2)
N2A—C2A—N3A—C4A179.27 (14)N2B—C2B—N3B—C4B177.54 (14)
N1A—C2A—N3A—C4A0.2 (2)N1B—C2B—N3B—C4B1.6 (2)
C2A—N3A—C4A—N4A178.70 (14)C2B—N3B—C4B—N4B178.34 (15)
C2A—N3A—C4A—C4AA1.7 (2)C2B—N3B—C4B—C4AB1.1 (2)
N4A—C4A—C4AA—N5A6.2 (2)N4B—C4B—C4AB—N5B4.1 (2)
N3A—C4A—C4AA—N5A173.38 (14)N3B—C4B—C4AB—N5B176.46 (15)
N4A—C4A—C4AA—C8AA177.64 (15)N4B—C4B—C4AB—C8AB179.72 (16)
N3A—C4A—C4AA—C8AA2.7 (2)N3B—C4B—C4AB—C8AB0.3 (2)
C8AA—C4AA—N5A—C6A1.1 (2)C8AB—C4AB—N5B—C6B0.3 (2)
C4A—C4AA—N5A—C6A177.05 (14)C4B—C4AB—N5B—C6B175.72 (14)
C4AA—N5A—C6A—C7A5.0 (2)C4AB—N5B—C6B—C7B4.2 (2)
C4AA—N5A—C6A—C9A172.51 (13)C4AB—N5B—C6B—C9B173.13 (13)
N5A—C6A—C7A—N7A173.77 (14)N5B—C6B—C7B—N7B175.17 (15)
C9A—C6A—C7A—N7A8.9 (2)C9B—C6B—C7B—N7B7.6 (2)
N5A—C6A—C7A—N8A7.0 (2)N5B—C6B—C7B—N8B4.9 (2)
C9A—C6A—C7A—N8A170.31 (14)C9B—C6B—C7B—N8B172.27 (14)
N7A—C7A—N8A—C8AA178.38 (14)N7B—C7B—N8B—C8AB178.85 (14)
C6A—C7A—N8A—C8AA2.4 (2)C6B—C7B—N8B—C8AB1.2 (2)
C7A—N8A—C8AA—N1A176.25 (13)C7B—N8B—C8AB—N1B178.03 (13)
C7A—N8A—C8AA—C4AA3.8 (2)C7B—N8B—C8AB—C4AB2.7 (2)
C2A—N1A—C8AA—N8A179.77 (14)C2B—N1B—C8AB—N8B179.99 (14)
C2A—N1A—C8AA—C4AA0.2 (2)C2B—N1B—C8AB—C4AB0.7 (2)
N5A—C4AA—C8AA—N8A5.9 (2)N5B—C4AB—C8AB—N8B3.4 (2)
C4A—C4AA—C8AA—N8A178.03 (14)C4B—C4AB—C8AB—N8B179.58 (14)
N5A—C4AA—C8AA—N1A174.17 (13)N5B—C4AB—C8AB—N1B177.33 (13)
C4A—C4AA—C8AA—N1A1.9 (2)C4B—C4AB—C8AB—N1B1.2 (2)
N5A—C6A—C9A—C14A118.55 (16)N5B—C6B—C9B—C10B72.73 (19)
C7A—C6A—C9A—C14A58.9 (2)C7B—C6B—C9B—C10B109.97 (17)
N5A—C6A—C9A—C10A55.58 (19)N5B—C6B—C9B—C14B100.17 (17)
C7A—C6A—C9A—C10A127.01 (16)C7B—C6B—C9B—C14B77.13 (19)
C14A—C9A—C10A—C11A0.4 (2)C14B—C9B—C10B—C11B1.7 (2)
C6A—C9A—C10A—C11A173.78 (14)C6B—C9B—C10B—C11B171.24 (15)
C9A—C10A—C11A—C12A1.3 (3)C9B—C10B—C11B—C12B0.1 (3)
C10A—C11A—C12A—C13A1.7 (3)C10B—C11B—C12B—C13B1.4 (3)
C11A—C12A—C13A—C14A0.5 (2)C11B—C12B—C13B—C14B1.1 (3)
C12A—C13A—C14A—C9A1.2 (2)C12B—C13B—C14B—C9B0.6 (2)
C10A—C9A—C14A—C13A1.7 (2)C10B—C9B—C14B—C13B2.0 (2)
C6A—C9A—C14A—C13A172.58 (13)C6B—C9B—C14B—C13B171.10 (13)
Triamterenium succinate, DMSO solvate (1b_DMSO) top
Crystal data top
C12H12N7+·C4H5O4·C2H6OSF(000) = 944
Mr = 449.49Dx = 1.420 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 13.5226 (7) ÅCell parameters from 8640 reflections
b = 14.9966 (7) Åθ = 1.0–27.5°
c = 10.6958 (5) ŵ = 0.20 mm1
β = 104.179 (2)°T = 220 K
V = 2102.95 (18) Å3Block, colourless
Z = 40.18 × 0.10 × 0.07 mm
Data collection top
Nonius Kappa CCD
diffractometer
4586 independent reflections
Radiation source: fine-focus sealed tube2099 reflections with I > 2σ(I)
None monochromatorRint = 0.042
Thin slice ω and φ scansθmax = 27.4°, θmin = 3.5°
Absorption correction: multi-scan
multi-scan from symmetry-related measurements Sortav (Blessing 1995)
h = 1417
Tmin = 0.841, Tmax = 1.000k = 1919
12060 measured reflectionsl = 1313
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036Hydrogen site location: difference Fourier map
wR(F2) = 0.074All H-atom parameters refined
S = 0.75 w = 1/[σ2(Fo2) + (0.0339P)2]
where P = (Fo2 + 2Fc2)/3
4586 reflections(Δ/σ)max = 0.001
372 parametersΔρmax = 0.31 e Å3
0 restraintsΔρmin = 0.31 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
N1A1.05320 (10)0.03264 (9)0.86586 (13)0.0326 (4)
C2A1.08847 (13)0.11235 (10)0.91829 (15)0.0307 (4)
N2A1.14807 (12)0.11192 (11)1.03579 (15)0.0393 (4)
N3A1.06604 (10)0.19013 (8)0.85559 (12)0.0333 (4)
C4A1.00405 (13)0.18843 (11)0.73612 (16)0.0326 (4)
N4A0.98281 (12)0.26490 (10)0.67422 (16)0.0401 (4)
N5A0.89096 (10)0.10676 (8)0.56186 (13)0.0334 (4)
C4AA0.96044 (12)0.10679 (10)0.67845 (15)0.0302 (4)
C6A0.85157 (12)0.02958 (10)0.51569 (15)0.0317 (4)
C7A0.88728 (13)0.05236 (10)0.58359 (16)0.0326 (4)
N7A0.85642 (13)0.13050 (10)0.53081 (16)0.0458 (5)
N8A0.95339 (10)0.05201 (8)0.69967 (13)0.0327 (4)
C8AA0.98766 (12)0.02834 (10)0.74614 (15)0.0300 (4)
C9A0.77068 (13)0.02975 (10)0.39273 (16)0.0313 (4)
C10A0.78585 (16)0.07409 (12)0.28532 (17)0.0392 (5)
C11A0.70797 (18)0.07927 (14)0.1739 (2)0.0525 (6)
C12A0.61483 (18)0.04069 (14)0.1687 (2)0.0548 (6)
C13A0.59860 (17)0.00311 (13)0.2735 (2)0.0500 (6)
C14A0.67612 (15)0.00922 (12)0.38525 (19)0.0418 (5)
C1B0.80332 (14)0.38476 (11)0.39161 (17)0.0374 (5)
O1B0.87992 (9)0.38466 (7)0.48458 (11)0.0427 (3)
C2B0.60890 (16)0.32680 (17)0.1488 (2)0.0591 (6)
O2B0.76081 (10)0.45462 (7)0.33840 (12)0.0551 (4)
C3B0.75909 (16)0.29521 (12)0.3403 (2)0.0470 (6)
O3B0.63185 (12)0.41104 (11)0.13400 (14)0.0723 (5)
C4B0.64446 (17)0.29038 (15)0.2839 (2)0.0533 (6)
O4B0.56016 (13)0.28359 (11)0.06050 (15)0.0947 (6)
C1C0.3455 (2)0.30097 (18)0.4108 (2)0.0580 (6)
O1C0.25405 (10)0.26687 (7)0.17183 (11)0.0549 (4)
S1C0.35932 (4)0.26335 (3)0.25988 (4)0.04554 (16)
C2C0.3818 (3)0.14855 (15)0.2971 (3)0.0671 (8)
H1XA1.0747 (13)0.0155 (10)0.9133 (15)0.045 (5)*
H2A1.1703 (11)0.0607 (11)1.0804 (15)0.037 (5)*
H3A1.1697 (11)0.1595 (10)1.0683 (14)0.028 (5)*
H4A1.0076 (14)0.3173 (13)0.7100 (16)0.064 (7)*
H5A0.9409 (12)0.2664 (9)0.5978 (16)0.030 (5)*
H6A0.8141 (12)0.1326 (9)0.4533 (14)0.030 (5)*
H7A0.8803 (12)0.1756 (10)0.5695 (15)0.030 (5)*
H10A0.8510 (12)0.1024 (9)0.2888 (13)0.029 (5)*
H11A0.7201 (13)0.1104 (10)0.1042 (17)0.052 (6)*
H12A0.5610 (13)0.0459 (10)0.0920 (17)0.049 (5)*
H13A0.5341 (13)0.0300 (11)0.2747 (15)0.050 (6)*
H14A0.6665 (12)0.0381 (10)0.4608 (15)0.042 (5)*
H3B0.6799 (18)0.4353 (15)0.220 (2)0.100 (8)*
H4B0.7783 (15)0.2533 (12)0.4052 (19)0.070 (7)*
H5B0.7945 (16)0.2741 (14)0.270 (2)0.092 (8)*
H6B0.6231 (13)0.2256 (12)0.2839 (16)0.059 (6)*
H7B0.6127 (13)0.3238 (12)0.3415 (16)0.055 (6)*
H1C0.3244 (15)0.3661 (14)0.4007 (18)0.079 (7)*
H2C0.4089 (15)0.2949 (12)0.4736 (19)0.068 (7)*
H3C0.2979 (17)0.2615 (13)0.435 (2)0.089 (9)*
H4C0.3868 (18)0.1228 (15)0.217 (2)0.108 (10)*
H5C0.317 (2)0.1314 (18)0.328 (3)0.142 (13)*
H6C0.4362 (14)0.1461 (11)0.3578 (18)0.052 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.0367 (9)0.0225 (8)0.0326 (9)0.0029 (7)0.0030 (7)0.0021 (7)
C2A0.0320 (11)0.0267 (10)0.0305 (10)0.0008 (8)0.0020 (9)0.0022 (8)
N2A0.0503 (11)0.0228 (9)0.0358 (10)0.0028 (8)0.0069 (8)0.0002 (8)
N3A0.0369 (9)0.0257 (8)0.0321 (9)0.0005 (7)0.0016 (7)0.0021 (7)
C4A0.0318 (11)0.0277 (10)0.0358 (11)0.0025 (8)0.0035 (9)0.0013 (8)
N4A0.0479 (11)0.0257 (9)0.0359 (10)0.0028 (8)0.0103 (8)0.0035 (8)
N5A0.0356 (9)0.0267 (8)0.0350 (9)0.0004 (7)0.0028 (7)0.0019 (7)
C4AA0.0316 (11)0.0240 (9)0.0305 (10)0.0012 (8)0.0008 (9)0.0008 (8)
C6A0.0318 (11)0.0291 (10)0.0318 (10)0.0005 (8)0.0033 (8)0.0006 (8)
C7A0.0344 (11)0.0236 (9)0.0359 (11)0.0005 (8)0.0016 (9)0.0008 (8)
N7A0.0571 (12)0.0274 (10)0.0378 (11)0.0015 (8)0.0172 (9)0.0028 (8)
N8A0.0356 (9)0.0242 (8)0.0334 (9)0.0011 (6)0.0009 (7)0.0020 (6)
C8AA0.0289 (10)0.0290 (10)0.0296 (10)0.0005 (8)0.0024 (8)0.0003 (8)
C9A0.0323 (11)0.0230 (9)0.0351 (11)0.0038 (8)0.0016 (9)0.0063 (8)
C10A0.0375 (13)0.0410 (11)0.0372 (12)0.0021 (10)0.0053 (10)0.0011 (9)
C11A0.0620 (17)0.0572 (14)0.0353 (13)0.0094 (12)0.0060 (12)0.0059 (11)
C12A0.0501 (16)0.0543 (14)0.0454 (14)0.0098 (12)0.0164 (13)0.0076 (11)
C13A0.0353 (14)0.0401 (12)0.0674 (16)0.0030 (10)0.0010 (12)0.0050 (11)
C14A0.0395 (13)0.0376 (11)0.0433 (13)0.0007 (9)0.0006 (11)0.0052 (10)
C1B0.0398 (12)0.0333 (11)0.0370 (11)0.0002 (9)0.0053 (10)0.0016 (9)
O1B0.0424 (8)0.0343 (7)0.0422 (7)0.0009 (6)0.0070 (7)0.0038 (6)
C2B0.0435 (14)0.0720 (16)0.0529 (15)0.0039 (12)0.0056 (11)0.0086 (13)
O2B0.0616 (9)0.0306 (7)0.0570 (9)0.0035 (7)0.0161 (7)0.0035 (6)
C3B0.0465 (15)0.0329 (11)0.0504 (14)0.0031 (10)0.0093 (12)0.0004 (10)
O3B0.0762 (12)0.0748 (11)0.0504 (10)0.0063 (9)0.0145 (8)0.0141 (8)
C4B0.0525 (16)0.0462 (14)0.0570 (16)0.0077 (11)0.0056 (13)0.0050 (12)
O4B0.0835 (12)0.1100 (13)0.0661 (11)0.0097 (10)0.0287 (9)0.0246 (9)
C1C0.0586 (18)0.0685 (18)0.0402 (14)0.0049 (14)0.0010 (13)0.0083 (12)
O1C0.0622 (9)0.0398 (7)0.0451 (8)0.0018 (6)0.0205 (7)0.0014 (6)
S1C0.0485 (3)0.0447 (3)0.0393 (3)0.0007 (3)0.0027 (2)0.0008 (2)
C2C0.077 (2)0.0519 (14)0.0570 (17)0.0219 (14)0.0128 (17)0.0037 (13)
Geometric parameters (Å, º) top
N1A—C2A1.3564 (18)C11A—H11A0.928 (17)
N1A—C8AA1.3687 (19)C12A—C13A1.363 (3)
N1A—H1XA0.889 (16)C12A—H12A0.957 (17)
C2A—N2A1.316 (2)C13A—C14A1.386 (3)
C2A—N3A1.3427 (18)C13A—H13A0.964 (17)
N2A—H2A0.915 (16)C14A—H14A0.953 (16)
N2A—H3A0.816 (15)C1B—O1B1.2479 (19)
N3A—C4A1.346 (2)C1B—O2B1.2616 (18)
C4A—N4A1.320 (2)C1B—C3B1.517 (2)
C4A—C4AA1.431 (2)C2B—O4B1.201 (2)
N4A—H4A0.901 (19)C2B—O3B1.320 (2)
N4A—H5A0.873 (16)C2B—C4B1.509 (3)
N5A—C6A1.3185 (18)C3B—C4B1.521 (3)
N5A—C4AA1.3653 (18)C3B—H4B0.925 (19)
C4AA—C8AA1.383 (2)C3B—H5B1.03 (2)
C6A—C7A1.449 (2)O3B—H3B1.05 (2)
C6A—C9A1.490 (2)C4B—H6B1.014 (17)
C7A—N7A1.323 (2)C4B—H7B0.973 (17)
C7A—N8A1.3406 (18)C1C—S1C1.763 (2)
N7A—H6A0.885 (15)C1C—H1C1.02 (2)
N7A—H7A0.816 (15)C1C—H2C0.96 (2)
N8A—C8AA1.3420 (19)C1C—H3C0.95 (2)
C9A—C10A1.385 (2)O1C—S1C1.5031 (12)
C9A—C14A1.390 (2)S1C—C2C1.776 (2)
C10A—C11A1.386 (2)C2C—H4C0.96 (2)
C10A—H10A0.971 (15)C2C—H5C1.04 (3)
C11A—C12A1.375 (3)C2C—H6C0.855 (18)
C2A—N1A—C8AA120.66 (14)C13A—C12A—H12A120.2 (10)
C2A—N1A—H1XA116.5 (10)C11A—C12A—H12A119.8 (10)
C8AA—N1A—H1XA122.8 (10)C12A—C13A—C14A120.1 (2)
N2A—C2A—N3A119.46 (15)C12A—C13A—H13A122.7 (10)
N2A—C2A—N1A117.48 (15)C14A—C13A—H13A117.2 (10)
N3A—C2A—N1A123.06 (14)C13A—C14A—C9A120.8 (2)
C2A—N2A—H2A123.2 (9)C13A—C14A—H14A121.9 (10)
C2A—N2A—H3A118.3 (10)C9A—C14A—H14A117.2 (10)
H2A—N2A—H3A118.3 (14)O1B—C1B—O2B123.92 (15)
C2A—N3A—C4A118.02 (13)O1B—C1B—C3B117.65 (16)
N4A—C4A—N3A117.92 (15)O2B—C1B—C3B118.43 (16)
N4A—C4A—C4AA120.72 (16)O4B—C2B—O3B121.5 (2)
N3A—C4A—C4AA121.35 (14)O4B—C2B—C4B122.9 (2)
C4A—N4A—H4A122.1 (11)O3B—C2B—C4B115.61 (18)
C4A—N4A—H5A120.2 (9)C1B—C3B—C4B117.31 (17)
H4A—N4A—H5A117.6 (15)C1B—C3B—H4B108.4 (11)
C6A—N5A—C4AA117.83 (13)C4B—C3B—H4B109.7 (13)
N5A—C4AA—C8AA120.87 (14)C1B—C3B—H5B108.8 (12)
N5A—C4AA—C4A120.84 (14)C4B—C3B—H5B107.8 (12)
C8AA—C4AA—C4A118.25 (15)H4B—C3B—H5B104.0 (17)
N5A—C6A—C7A120.16 (14)C2B—O3B—H3B109.9 (12)
N5A—C6A—C9A118.09 (14)C2B—C4B—C3B114.66 (19)
C7A—C6A—C9A121.75 (14)C2B—C4B—H6B108.9 (9)
N7A—C7A—N8A117.88 (15)C3B—C4B—H6B108.0 (10)
N7A—C7A—C6A120.39 (15)C2B—C4B—H7B109.5 (10)
N8A—C7A—C6A121.72 (14)C3B—C4B—H7B106.9 (11)
C7A—N7A—H6A119.7 (9)H6B—C4B—H7B108.8 (15)
C7A—N7A—H7A118.2 (11)S1C—C1C—H1C107.5 (11)
H6A—N7A—H7A121.9 (14)S1C—C1C—H2C109.6 (12)
C7A—N8A—C8AA115.97 (14)H1C—C1C—H2C110.2 (15)
N8A—C8AA—N1A118.33 (14)S1C—C1C—H3C106.1 (13)
N8A—C8AA—C4AA123.13 (15)H1C—C1C—H3C115.8 (18)
N1A—C8AA—C4AA118.55 (15)H2C—C1C—H3C107.5 (18)
C10A—C9A—C14A118.35 (17)O1C—S1C—C1C105.42 (11)
C10A—C9A—C6A120.45 (16)O1C—S1C—C2C104.95 (11)
C14A—C9A—C6A121.06 (16)C1C—S1C—C2C98.96 (14)
C9A—C10A—C11A120.3 (2)S1C—C2C—H4C103.5 (13)
C9A—C10A—H10A119.7 (9)S1C—C2C—H5C101.6 (15)
C11A—C10A—H10A120.0 (9)H4C—C2C—H5C116 (2)
C12A—C11A—C10A120.5 (2)S1C—C2C—H6C106.2 (12)
C12A—C11A—H11A121.3 (11)H4C—C2C—H6C115 (2)
C10A—C11A—H11A118.2 (11)H5C—C2C—H6C112 (2)
C13A—C12A—C11A120.0 (2)
C8AA—N1A—C2A—N2A177.39 (16)C2A—N1A—C8AA—C4AA1.7 (2)
C8AA—N1A—C2A—N3A3.2 (3)N5A—C4AA—C8AA—N8A4.2 (3)
N2A—C2A—N3A—C4A179.32 (16)C4A—C4AA—C8AA—N8A178.22 (16)
N1A—C2A—N3A—C4A1.3 (2)N5A—C4AA—C8AA—N1A176.31 (15)
C2A—N3A—C4A—N4A179.43 (15)C4A—C4AA—C8AA—N1A1.3 (2)
C2A—N3A—C4A—C4AA1.9 (3)N5A—C6A—C9A—C10A51.1 (2)
C6A—N5A—C4AA—C8AA0.6 (2)C7A—C6A—C9A—C10A128.59 (18)
C6A—N5A—C4AA—C4A178.17 (15)N5A—C6A—C9A—C14A124.59 (17)
N4A—C4A—C4AA—N5A4.2 (3)C7A—C6A—C9A—C14A55.7 (2)
N3A—C4A—C4AA—N5A174.40 (15)C14A—C9A—C10A—C11A0.2 (3)
N4A—C4A—C4AA—C8AA178.17 (16)C6A—C9A—C10A—C11A175.59 (16)
N3A—C4A—C4AA—C8AA3.2 (3)C9A—C10A—C11A—C12A0.1 (3)
C4AA—N5A—C6A—C7A4.3 (2)C10A—C11A—C12A—C13A0.1 (3)
C4AA—N5A—C6A—C9A176.04 (15)C11A—C12A—C13A—C14A0.4 (3)
N5A—C6A—C7A—N7A172.47 (17)C12A—C13A—C14A—C9A0.7 (3)
C9A—C6A—C7A—N7A7.2 (3)C10A—C9A—C14A—C13A0.6 (3)
N5A—C6A—C7A—N8A6.3 (2)C6A—C9A—C14A—C13A175.15 (16)
C9A—C6A—C7A—N8A174.02 (16)O1B—C1B—C3B—C4B148.26 (19)
N7A—C7A—N8A—C8AA175.97 (16)O2B—C1B—C3B—C4B31.6 (3)
C6A—C7A—N8A—C8AA2.8 (2)O4B—C2B—C4B—C3B123.5 (2)
C7A—N8A—C8AA—N1A178.26 (15)O3B—C2B—C4B—C3B58.8 (3)
C7A—N8A—C8AA—C4AA2.2 (2)C1B—C3B—C4B—C2B78.5 (3)
C2A—N1A—C8AA—N8A178.70 (15)
Triamterenium adipate, DMSO solvate (1c_DMSO) top
Crystal data top
2(C12H12N7)·C6H8O4·2(C2H6OS)Z = 2
Mr = 808.95F(000) = 852
Triclinic, P1Dx = 1.414 Mg m3
a = 11.0286 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 13.7429 (4) ÅCell parameters from 40707 reflections
c = 14.9742 (5) Åθ = 1.0–25.4°
α = 115.247 (2)°µ = 0.21 mm1
β = 109.951 (4)°T = 180 K
γ = 90.122 (2)°Block, colourless
V = 1900.24 (11) Å30.12 × 0.05 × 0.02 mm
Data collection top
Nonius Kappa CCD
diffractometer
6951 independent reflections
Radiation source: sealed X-ray tube5118 reflections with I > 2σ(I)
None monochromatorRint = 0.052
Thin slice ω and φ scansθmax = 25.4°, θmin = 3.6°
Absorption correction: multi-scan
multi-scan from symmetry-related measurements Sortav (Blessing 1995)
h = 1312
Tmin = 0.894, Tmax = 1.000k = 1616
25204 measured reflectionsl = 1818
Refinement top
Refinement on F2Primary atom site location: difference Fourier map
Least-squares matrix: fullSecondary atom site location: structure-invariant direct methods
R[F2 > 2σ(F2)] = 0.073Hydrogen site location: mixed
wR(F2) = 0.191H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0749P)2 + 4.0839P]
where P = (Fo2 + 2Fc2)/3
6951 reflections(Δ/σ)max < 0.001
520 parametersΔρmax = 1.61 e Å3
18 restraintsΔρmin = 0.66 e Å3
Special details top

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
N1A0.3191 (3)0.2248 (2)0.1399 (2)0.0278 (6)
C2A0.2342 (3)0.2886 (3)0.1739 (3)0.0282 (7)
N2A0.2583 (3)0.3930 (2)0.1995 (3)0.0369 (7)
H3A0.20430.43630.22020.044*
H2A0.32820.41940.19590.044*
N3A0.1270 (3)0.2501 (2)0.1800 (2)0.0287 (6)
C4A0.1028 (3)0.1430 (3)0.1529 (3)0.0263 (7)
C4AA0.1927 (3)0.0729 (3)0.1223 (3)0.0258 (7)
N4A0.0044 (3)0.1035 (2)0.1547 (2)0.0316 (7)
H4A0.05930.14690.17340.038*
H5A0.02140.03380.13710.038*
N5A0.1757 (3)0.0320 (2)0.1071 (2)0.0276 (6)
C6A0.2613 (3)0.0922 (3)0.0799 (3)0.0268 (7)
C7A0.3626 (3)0.0504 (3)0.0571 (3)0.0283 (7)
N7A0.4380 (3)0.1160 (3)0.0157 (3)0.0350 (7)
N8A0.3825 (3)0.0542 (2)0.0770 (2)0.0277 (6)
C8AA0.2991 (3)0.1156 (3)0.1126 (3)0.0259 (7)
C9A0.2507 (3)0.2024 (3)0.0749 (3)0.0281 (7)
C10A0.1383 (4)0.2807 (3)0.0047 (3)0.0355 (8)
H10A0.07020.26570.04460.043*
C11A0.1248 (4)0.3801 (3)0.0059 (3)0.0410 (9)
H11A0.04890.43380.04350.049*
C12A0.2224 (4)0.4008 (3)0.0793 (3)0.0403 (9)
H12A0.21230.46840.08150.048*
C13A0.3342 (4)0.3244 (3)0.1494 (3)0.0340 (8)*
H13A0.40080.33920.19970.041*
C14A0.3494 (4)0.2254 (3)0.1465 (3)0.0319 (8)*
H14A0.42760.17350.19350.038*
N1B0.3412 (3)0.7274 (2)0.6746 (2)0.0264 (6)
C2B0.2728 (3)0.7927 (3)0.7304 (3)0.0271 (7)
N2B0.3006 (3)0.8988 (2)0.7636 (2)0.0330 (7)
H3B0.25780.94360.79880.040*
H2B0.36210.92480.75050.040*
N3B0.1786 (3)0.7550 (2)0.7514 (2)0.0283 (6)
C4B0.1492 (3)0.6471 (3)0.7147 (3)0.0296 (8)
N4B0.0531 (3)0.6080 (2)0.7311 (3)0.0379 (8)
H4B0.00980.65300.76570.045*
H5B0.03250.53720.70740.045*
C4AB0.2170 (3)0.5734 (3)0.6559 (3)0.0272 (7)
N5B0.1853 (3)0.4641 (2)0.6194 (2)0.0279 (6)
C6B0.2464 (3)0.3995 (3)0.5629 (3)0.0256 (7)
C7B0.3414 (3)0.4440 (3)0.5364 (3)0.0271 (7)
N7B0.3961 (3)0.3771 (3)0.4725 (3)0.0364 (8)
N8B0.3748 (3)0.5520 (2)0.5745 (2)0.0280 (6)
C8AB0.3126 (3)0.6159 (3)0.6349 (3)0.0259 (7)
C9B0.2127 (3)0.2808 (3)0.5274 (3)0.0282 (7)
C10B0.1146 (4)0.2160 (3)0.4304 (3)0.0401 (9)
H10B0.07520.24560.38260.048*
C11B0.0728 (4)0.1076 (3)0.4016 (3)0.0463 (10)
H11B0.00470.06360.33460.056*
C12B0.1299 (4)0.0642 (3)0.4700 (3)0.0445 (10)
H12B0.09980.00940.45110.053*
C13B0.2306 (4)0.1272 (3)0.5659 (3)0.0451 (10)
H13B0.27190.09610.61190.054*
C14B0.2724 (4)0.2355 (3)0.5957 (3)0.0382 (9)
H14B0.34130.27890.66240.046*
C1C0.4875 (3)0.0816 (3)0.3554 (3)0.0288 (8)
O1C0.4799 (3)0.17533 (19)0.3599 (2)0.0354 (6)
C2C0.3924 (4)0.0374 (3)0.3879 (3)0.0330 (8)
H1C0.31440.00760.32300.040*
H2C0.36290.09980.43490.040*
O2C0.5644 (3)0.0226 (2)0.3227 (2)0.0423 (7)
C3C0.4463 (4)0.0317 (3)0.4457 (3)0.0334 (8)
H3C0.37350.06490.45370.040*
H4C0.48060.09190.40070.040*
C1D0.5282 (3)0.4207 (3)0.1422 (3)0.0270 (7)
O1D0.5016 (3)0.31838 (19)0.1063 (2)0.0367 (6)
C2D0.6224 (3)0.4627 (3)0.1068 (3)0.0313 (8)
H1D0.64950.39960.05820.038*
H2D0.70180.50780.17000.038*
O2D0.4832 (2)0.48912 (19)0.2044 (2)0.0340 (6)
C3D0.5618 (3)0.5307 (3)0.0497 (3)0.0302 (8)
H3D0.54050.59640.10010.036*
H4D0.62760.55580.02920.036*
S1E0.16128 (11)0.67740 (8)0.32485 (8)0.0452 (3)
O1E0.0858 (3)0.5633 (2)0.2590 (2)0.0462 (7)
C1E0.3249 (4)0.6647 (4)0.3889 (3)0.0499 (11)
H1E0.36400.63020.33550.075*
H2E0.32450.61970.42490.075*
H3E0.37640.73740.44140.075*
C2E0.1180 (6)0.7352 (4)0.4396 (4)0.0682 (14)
H4E0.02980.75300.41940.102*
H5E0.18080.80190.49440.102*
H6E0.11970.68250.46780.102*
S1F0.14448 (15)1.14703 (12)0.80626 (12)0.0427 (4)0.7
O1F0.1590 (7)1.0752 (4)0.8691 (4)0.0483 (6)*0.7
C1F0.3122 (6)1.1906 (6)0.8335 (6)0.0483 (6)*0.7
H1F0.34861.12760.79680.072*0.7
H2F0.36261.22320.91050.072*0.7
H3F0.31691.24490.80800.072*0.7
C2F0.1117 (6)1.2723 (5)0.8905 (5)0.0483 (6)*0.7
H4F0.02421.26060.89070.072*0.7
H5F0.11581.32590.86410.072*0.7
H6F0.17711.29960.96320.072*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'0.36231.21640.87750.072*0.3
H2F'0.25441.26920.81820.072*0.3
H3F'0.25131.14010.76320.072*0.3
C2F'0.0143 (12)1.1951 (12)0.8031 (11)0.0483 (6)*0.3
H4F'0.05901.15120.79950.072*0.3
H5F'0.01871.16670.73230.072*0.3
H6F'0.00141.27130.82710.072*0.3
H1XA0.375 (4)0.253 (3)0.128 (3)0.038 (11)*
H1XB0.410 (5)0.761 (4)0.670 (4)0.075 (16)*
H6A0.422 (4)0.184 (3)0.006 (3)0.029 (10)*
H7A0.489 (4)0.091 (4)0.001 (3)0.043 (12)*
H6B0.381 (4)0.310 (3)0.453 (3)0.032 (10)*
H7B0.455 (5)0.403 (4)0.458 (3)0.047 (12)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.0299 (16)0.0246 (15)0.0392 (17)0.0094 (13)0.0233 (14)0.0155 (13)
C2A0.0316 (19)0.0280 (18)0.0313 (18)0.0084 (15)0.0181 (15)0.0141 (15)
N2A0.0388 (18)0.0267 (16)0.061 (2)0.0150 (13)0.0350 (16)0.0208 (15)
N3A0.0303 (16)0.0265 (15)0.0374 (16)0.0096 (12)0.0204 (13)0.0158 (13)
C4A0.0281 (18)0.0277 (18)0.0268 (17)0.0066 (14)0.0148 (14)0.0121 (14)
C4AA0.0276 (18)0.0247 (17)0.0303 (18)0.0078 (14)0.0164 (15)0.0128 (14)
N4A0.0302 (16)0.0244 (15)0.0457 (18)0.0093 (12)0.0239 (14)0.0134 (13)
N5A0.0294 (15)0.0281 (15)0.0288 (15)0.0082 (12)0.0158 (12)0.0124 (12)
C6A0.0277 (18)0.0280 (18)0.0295 (17)0.0092 (14)0.0162 (14)0.0133 (14)
C7A0.0297 (18)0.0300 (18)0.0312 (18)0.0108 (15)0.0171 (15)0.0148 (15)
N7A0.043 (2)0.0251 (18)0.054 (2)0.0145 (15)0.0350 (17)0.0202 (16)
N8A0.0307 (16)0.0271 (15)0.0355 (16)0.0125 (12)0.0213 (13)0.0163 (13)
C8AA0.0310 (18)0.0265 (17)0.0249 (17)0.0092 (14)0.0146 (14)0.0128 (14)
C9A0.0321 (19)0.0260 (17)0.0334 (18)0.0111 (15)0.0217 (15)0.0126 (15)
C10A0.035 (2)0.032 (2)0.041 (2)0.0081 (16)0.0169 (17)0.0165 (17)
C11A0.039 (2)0.033 (2)0.052 (2)0.0033 (17)0.0225 (19)0.0157 (18)
C12A0.058 (3)0.032 (2)0.055 (2)0.0204 (19)0.041 (2)0.0258 (19)
N1B0.0276 (15)0.0230 (15)0.0342 (16)0.0072 (12)0.0196 (13)0.0118 (12)
C2B0.0265 (18)0.0278 (18)0.0287 (17)0.0066 (14)0.0129 (14)0.0125 (15)
N2B0.0349 (17)0.0242 (15)0.0496 (19)0.0095 (13)0.0291 (15)0.0153 (14)
N3B0.0300 (16)0.0255 (15)0.0363 (16)0.0089 (12)0.0211 (13)0.0134 (13)
C4B0.0313 (19)0.0292 (18)0.0346 (19)0.0084 (15)0.0186 (15)0.0151 (15)
N4B0.0435 (19)0.0254 (15)0.056 (2)0.0101 (14)0.0366 (16)0.0147 (15)
C4AB0.0280 (18)0.0257 (17)0.0304 (18)0.0062 (14)0.0151 (15)0.0119 (14)
N5B0.0278 (15)0.0292 (15)0.0311 (15)0.0084 (12)0.0159 (13)0.0140 (13)
C6B0.0269 (18)0.0267 (17)0.0253 (17)0.0077 (14)0.0128 (14)0.0115 (14)
C7B0.0287 (18)0.0276 (18)0.0293 (18)0.0090 (14)0.0151 (15)0.0135 (15)
N7B0.046 (2)0.0232 (17)0.051 (2)0.0094 (15)0.0352 (17)0.0143 (15)
N8B0.0316 (16)0.0256 (15)0.0334 (16)0.0089 (12)0.0198 (13)0.0135 (13)
C8AB0.0274 (18)0.0260 (17)0.0287 (17)0.0077 (14)0.0138 (14)0.0139 (14)
C9B0.0292 (18)0.0291 (18)0.0344 (19)0.0099 (15)0.0212 (15)0.0144 (15)
C10B0.044 (2)0.031 (2)0.040 (2)0.0079 (17)0.0113 (18)0.0151 (17)
C11B0.042 (2)0.032 (2)0.049 (2)0.0002 (18)0.0130 (19)0.0084 (19)
C12B0.054 (3)0.028 (2)0.057 (3)0.0044 (18)0.034 (2)0.0143 (19)
C13B0.064 (3)0.040 (2)0.053 (3)0.020 (2)0.035 (2)0.030 (2)
C14B0.047 (2)0.032 (2)0.036 (2)0.0085 (17)0.0175 (18)0.0151 (17)
C1C0.0337 (19)0.0277 (18)0.0266 (17)0.0048 (15)0.0130 (15)0.0127 (15)
O1C0.0431 (15)0.0259 (13)0.0465 (15)0.0090 (11)0.0287 (13)0.0155 (11)
C2C0.035 (2)0.0343 (19)0.036 (2)0.0075 (16)0.0185 (16)0.0182 (16)
O2C0.0560 (17)0.0357 (15)0.0599 (18)0.0208 (13)0.0414 (15)0.0281 (13)
C3C0.042 (2)0.0291 (18)0.037 (2)0.0054 (16)0.0221 (17)0.0164 (16)
C1D0.0278 (18)0.0317 (19)0.0301 (18)0.0107 (15)0.0149 (15)0.0184 (15)
O1D0.0436 (15)0.0266 (13)0.0511 (16)0.0111 (11)0.0320 (13)0.0166 (12)
C2D0.0308 (19)0.0354 (19)0.0368 (19)0.0095 (15)0.0190 (16)0.0195 (16)
O2D0.0415 (15)0.0295 (13)0.0426 (14)0.0108 (11)0.0271 (12)0.0179 (11)
C3D0.035 (2)0.0278 (18)0.0343 (19)0.0057 (15)0.0177 (16)0.0157 (15)
S1E0.0561 (7)0.0367 (6)0.0458 (6)0.0063 (5)0.0233 (5)0.0183 (5)
O1E0.0465 (17)0.0378 (15)0.0500 (17)0.0009 (13)0.0221 (14)0.0132 (13)
C1E0.048 (3)0.048 (3)0.046 (2)0.002 (2)0.016 (2)0.017 (2)
C2E0.079 (4)0.068 (3)0.055 (3)0.023 (3)0.038 (3)0.016 (3)
S1F0.0437 (8)0.0373 (8)0.0445 (8)0.0036 (6)0.0184 (7)0.0150 (6)
Geometric parameters (Å, º) top
N1A—C2A1.361 (4)C9B—C14B1.398 (5)
N1A—C8AA1.372 (4)C10B—C11B1.389 (5)
N1A—H1XA0.83 (4)C10B—H10B0.9500
C2A—N2A1.317 (4)C11B—C12B1.373 (6)
C2A—N3A1.341 (4)C11B—H11B0.9500
N2A—H3A0.8800C12B—C13B1.376 (6)
N2A—H2A0.8800C12B—H12B0.9500
N3A—C4A1.348 (4)C13B—C14B1.385 (5)
C4A—N4A1.314 (4)C13B—H13B0.9500
C4A—C4AA1.435 (4)C14B—H14B0.9500
C4AA—N5A1.362 (4)C1C—O2C1.251 (4)
C4AA—C8AA1.389 (5)C1C—O1C1.266 (4)
N4A—H4A0.8800C1C—C2C1.518 (5)
N4A—H5A0.8800C2C—C3C1.534 (5)
N5A—C6A1.311 (4)C2C—H1C0.9900
C6A—C7A1.455 (5)C2C—H2C0.9900
C6A—C9A1.487 (5)C3C—C3Ci1.510 (7)
C7A—N7A1.329 (4)C3C—H3C0.9900
C7A—N8A1.339 (4)C3C—H4C0.9900
N7A—H6A0.84 (4)C1D—O2D1.253 (4)
N7A—H7A0.81 (5)C1D—O1D1.265 (4)
N8A—C8AA1.340 (4)C1D—C2D1.525 (5)
C9A—C14A1.389 (5)C2D—C3D1.532 (5)
C9A—C10A1.393 (5)C2D—H1D0.9900
C10A—C11A1.381 (5)C2D—H2D0.9900
C10A—H10A0.9500C3D—C3Dii1.525 (7)
C11A—C12A1.383 (6)C3D—H3D0.9900
C11A—H11A0.9500C3D—H4D0.9900
C12A—C13A1.376 (6)S1E—O1E1.497 (3)
C12A—H12A0.9500S1E—C1E1.780 (4)
C13A—C14A1.391 (5)S1E—C2E1.791 (5)
C13A—H13A0.9500C1E—H1E0.9800
C14A—H14A0.9500C1E—H2E0.9800
N1B—C2B1.367 (4)C1E—H3E0.9800
N1B—C8AB1.376 (4)C2E—H4E0.9800
N1B—H1XB0.92 (6)C2E—H5E0.9800
C2B—N2B1.321 (4)C2E—H6E0.9800
C2B—N3B1.345 (4)S1F—O1F1.605 (6)
N2B—H3B0.8800S1F—C2F1.773 (6)
N2B—H2B0.8800S1F—C1F1.794 (6)
N3B—C4B1.336 (4)C1F—H1F0.9800
C4B—N4B1.328 (4)C1F—H2F0.9800
C4B—C4AB1.432 (5)C1F—H3F0.9800
N4B—H4B0.8800C2F—H4F0.9800
N4B—H5B0.8800C2F—H5F0.9800
C4AB—N5B1.358 (4)C2F—H6F0.9800
C4AB—C8AB1.391 (5)S1F'—O1F'1.507 (11)
N5B—C6B1.307 (4)S1F'—C2F'1.800 (11)
C6B—C7B1.456 (5)S1F'—C1F'1.821 (12)
C6B—C9B1.484 (5)C1F'—H1F'0.9800
C7B—N7B1.330 (4)C1F'—H2F'0.9800
C7B—N8B1.339 (4)C1F'—H3F'0.9800
N7B—H6B0.83 (4)C2F'—H4F'0.9800
N7B—H7B0.86 (5)C2F'—H5F'0.9800
N8B—C8AB1.345 (4)C2F'—H6F'0.9800
C9B—C10B1.376 (5)
C2A—N1A—C8AA120.0 (3)C11B—C10B—H10B119.7
C2A—N1A—H1XA117 (3)C12B—C11B—C10B120.0 (4)
C8AA—N1A—H1XA122 (3)C12B—C11B—H11B120.0
N2A—C2A—N3A119.0 (3)C10B—C11B—H11B120.0
N2A—C2A—N1A117.6 (3)C11B—C12B—C13B119.9 (4)
N3A—C2A—N1A123.4 (3)C11B—C12B—H12B120.0
C2A—N2A—H3A120.0C13B—C12B—H12B120.0
C2A—N2A—H2A120.0C12B—C13B—C14B120.5 (4)
H3A—N2A—H2A120.0C12B—C13B—H13B119.7
C2A—N3A—C4A118.5 (3)C14B—C13B—H13B119.7
N4A—C4A—N3A119.1 (3)C13B—C14B—C9B119.7 (4)
N4A—C4A—C4AA120.3 (3)C13B—C14B—H14B120.1
N3A—C4A—C4AA120.6 (3)C9B—C14B—H14B120.1
N5A—C4AA—C8AA121.2 (3)O2C—C1C—O1C124.3 (3)
N5A—C4AA—C4A120.2 (3)O2C—C1C—C2C118.7 (3)
C8AA—C4AA—C4A118.6 (3)O1C—C1C—C2C117.0 (3)
C4A—N4A—H4A120.0C1C—C2C—C3C115.5 (3)
C4A—N4A—H5A120.0C1C—C2C—H1C108.4
H4A—N4A—H5A120.0C3C—C2C—H1C108.4
C6A—N5A—C4AA117.6 (3)C1C—C2C—H2C108.4
N5A—C6A—C7A120.4 (3)C3C—C2C—H2C108.4
N5A—C6A—C9A117.3 (3)H1C—C2C—H2C107.5
C7A—C6A—C9A122.4 (3)C3Ci—C3C—C2C114.1 (4)
N7A—C7A—N8A118.3 (3)C3Ci—C3C—H3C108.7
N7A—C7A—C6A120.4 (3)C2C—C3C—H3C108.7
N8A—C7A—C6A121.4 (3)C3Ci—C3C—H4C108.7
C7A—N7A—H6A121 (3)C2C—C3C—H4C108.7
C7A—N7A—H7A117 (3)H3C—C3C—H4C107.6
H6A—N7A—H7A120 (4)O2D—C1D—O1D124.7 (3)
C7A—N8A—C8AA116.1 (3)O2D—C1D—C2D118.3 (3)
N8A—C8AA—N1A118.7 (3)O1D—C1D—C2D117.0 (3)
N8A—C8AA—C4AA122.6 (3)C1D—C2D—C3D112.7 (3)
N1A—C8AA—C4AA118.7 (3)C1D—C2D—H1D109.1
C14A—C9A—C10A119.1 (3)C3D—C2D—H1D109.1
C14A—C9A—C6A119.9 (3)C1D—C2D—H2D109.1
C10A—C9A—C6A120.9 (3)C3D—C2D—H2D109.1
C11A—C10A—C9A120.6 (4)H1D—C2D—H2D107.8
C11A—C10A—H10A119.7C3Dii—C3D—C2D113.8 (4)
C9A—C10A—H10A119.7C3Dii—C3D—H3D108.8
C10A—C11A—C12A119.6 (4)C2D—C3D—H3D108.8
C10A—C11A—H11A120.2C3Dii—C3D—H4D108.8
C12A—C11A—H11A120.2C2D—C3D—H4D108.8
C13A—C12A—C11A120.5 (4)H3D—C3D—H4D107.7
C13A—C12A—H12A119.7O1E—S1E—C1E105.73 (19)
C11A—C12A—H12A119.7O1E—S1E—C2E105.9 (2)
C12A—C13A—C14A119.9 (3)C1E—S1E—C2E98.2 (2)
C12A—C13A—H13A120.0S1E—C1E—H1E109.5
C14A—C13A—H13A120.0S1E—C1E—H2E109.5
C9A—C14A—C13A120.1 (3)H1E—C1E—H2E109.5
C9A—C14A—H14A119.9S1E—C1E—H3E109.5
C13A—C14A—H14A119.9H1E—C1E—H3E109.5
C2B—N1B—C8AB119.5 (3)H2E—C1E—H3E109.5
C2B—N1B—H1XB118 (3)S1E—C2E—H4E109.5
C8AB—N1B—H1XB123 (3)S1E—C2E—H5E109.5
N2B—C2B—N3B118.9 (3)H4E—C2E—H5E109.5
N2B—C2B—N1B117.2 (3)S1E—C2E—H6E109.5
N3B—C2B—N1B123.9 (3)H4E—C2E—H6E109.5
C2B—N2B—H3B120.0H5E—C2E—H6E109.5
C2B—N2B—H2B120.0O1F—S1F—C2F103.9 (3)
H3B—N2B—H2B120.0O1F—S1F—C1F101.9 (3)
C4B—N3B—C2B118.1 (3)C2F—S1F—C1F99.0 (3)
N4B—C4B—N3B118.9 (3)S1F—C1F—H1F109.5
N4B—C4B—C4AB119.8 (3)S1F—C1F—H2F109.5
N3B—C4B—C4AB121.3 (3)H1F—C1F—H2F109.5
C4B—N4B—H4B120.0S1F—C1F—H3F109.5
C4B—N4B—H5B120.0H1F—C1F—H3F109.5
H4B—N4B—H5B120.0H2F—C1F—H3F109.5
N5B—C4AB—C8AB121.1 (3)S1F—C2F—H4F109.5
N5B—C4AB—C4B120.2 (3)S1F—C2F—H5F109.5
C8AB—C4AB—C4B118.7 (3)H4F—C2F—H5F109.5
C6B—N5B—C4AB118.2 (3)S1F—C2F—H6F109.5
N5B—C6B—C7B120.4 (3)H4F—C2F—H6F109.5
N5B—C6B—C9B116.8 (3)H5F—C2F—H6F109.5
C7B—C6B—C9B122.8 (3)O1F'—S1F'—C2F'96.2 (7)
N7B—C7B—N8B118.8 (3)O1F'—S1F'—C1F'98.6 (8)
N7B—C7B—C6B120.0 (3)C2F'—S1F'—C1F'96.6 (7)
N8B—C7B—C6B121.2 (3)S1F'—C1F'—H1F'109.5
C7B—N7B—H6B119 (3)S1F'—C1F'—H2F'109.5
C7B—N7B—H7B120 (3)H1F'—C1F'—H2F'109.5
H6B—N7B—H7B120 (4)S1F'—C1F'—H3F'109.5
C7B—N8B—C8AB116.5 (3)H1F'—C1F'—H3F'109.5
N8B—C8AB—N1B119.0 (3)H2F'—C1F'—H3F'109.5
N8B—C8AB—C4AB122.4 (3)S1F'—C2F'—H4F'109.5
N1B—C8AB—C4AB118.5 (3)S1F'—C2F'—H5F'109.5
C10B—C9B—C14B119.1 (3)H4F'—C2F'—H5F'109.5
C10B—C9B—C6B120.3 (3)S1F'—C2F'—H6F'109.5
C14B—C9B—C6B120.3 (3)H4F'—C2F'—H6F'109.5
C9B—C10B—C11B120.6 (4)H5F'—C2F'—H6F'109.5
C9B—C10B—H10B119.7
C8AA—N1A—C2A—N2A179.7 (3)N1B—C2B—N3B—C4B0.6 (5)
C8AA—N1A—C2A—N3A2.0 (5)C2B—N3B—C4B—N4B177.5 (3)
N2A—C2A—N3A—C4A179.5 (3)C2B—N3B—C4B—C4AB0.9 (5)
N1A—C2A—N3A—C4A1.3 (5)N4B—C4B—C4AB—N5B1.7 (5)
C2A—N3A—C4A—N4A177.5 (3)N3B—C4B—C4AB—N5B180.0 (3)
C2A—N3A—C4A—C4AA2.4 (5)N4B—C4B—C4AB—C8AB176.6 (3)
N4A—C4A—C4AA—N5A7.7 (5)N3B—C4B—C4AB—C8AB1.7 (5)
N3A—C4A—C4AA—N5A172.3 (3)C8AB—C4AB—N5B—C6B0.6 (5)
N4A—C4A—C4AA—C8AA174.6 (3)C4B—C4AB—N5B—C6B177.6 (3)
N3A—C4A—C4AA—C8AA5.4 (5)C4AB—N5B—C6B—C7B2.7 (5)
C8AA—C4AA—N5A—C6A2.0 (5)C4AB—N5B—C6B—C9B178.0 (3)
C4A—C4AA—N5A—C6A179.6 (3)N5B—C6B—C7B—N7B175.1 (3)
C4AA—N5A—C6A—C7A5.7 (5)C9B—C6B—C7B—N7B4.2 (5)
C4AA—N5A—C6A—C9A173.5 (3)N5B—C6B—C7B—N8B4.3 (5)
N5A—C6A—C7A—N7A170.9 (3)C9B—C6B—C7B—N8B176.4 (3)
C9A—C6A—C7A—N7A10.0 (5)N7B—C7B—N8B—C8AB177.2 (3)
N5A—C6A—C7A—N8A9.1 (5)C6B—C7B—N8B—C8AB2.3 (5)
C9A—C6A—C7A—N8A170.1 (3)C7B—N8B—C8AB—N1B178.8 (3)
N7A—C7A—N8A—C8AA176.1 (3)C7B—N8B—C8AB—C4AB1.1 (5)
C6A—C7A—N8A—C8AA3.8 (5)C2B—N1B—C8AB—N8B175.9 (3)
C7A—N8A—C8AA—N1A176.4 (3)C2B—N1B—C8AB—C4AB1.9 (5)
C7A—N8A—C8AA—C4AA4.0 (5)N5B—C4AB—C8AB—N8B2.7 (5)
C2A—N1A—C8AA—N8A178.5 (3)C4B—C4AB—C8AB—N8B175.6 (3)
C2A—N1A—C8AA—C4AA1.1 (5)N5B—C4AB—C8AB—N1B179.6 (3)
N5A—C4AA—C8AA—N8A7.4 (5)C4B—C4AB—C8AB—N1B2.1 (5)
C4A—C4AA—C8AA—N8A175.0 (3)N5B—C6B—C9B—C10B91.3 (4)
N5A—C4AA—C8AA—N1A173.1 (3)C7B—C6B—C9B—C10B88.0 (4)
C4A—C4AA—C8AA—N1A4.6 (5)N5B—C6B—C9B—C14B83.3 (4)
N5A—C6A—C9A—C14A113.9 (4)C7B—C6B—C9B—C14B97.4 (4)
C7A—C6A—C9A—C14A65.3 (4)C14B—C9B—C10B—C11B1.7 (6)
N5A—C6A—C9A—C10A61.2 (4)C6B—C9B—C10B—C11B173.0 (3)
C7A—C6A—C9A—C10A119.6 (4)C9B—C10B—C11B—C12B0.3 (6)
C14A—C9A—C10A—C11A0.0 (5)C10B—C11B—C12B—C13B1.6 (6)
C6A—C9A—C10A—C11A175.1 (3)C11B—C12B—C13B—C14B2.1 (6)
C9A—C10A—C11A—C12A1.6 (6)C12B—C13B—C14B—C9B0.8 (6)
C10A—C11A—C12A—C13A1.6 (6)C10B—C9B—C14B—C13B1.1 (5)
C11A—C12A—C13A—C14A0.1 (5)C6B—C9B—C14B—C13B173.5 (3)
C10A—C9A—C14A—C13A1.7 (5)O2C—C1C—C2C—C3C37.8 (5)
C6A—C9A—C14A—C13A173.5 (3)O1C—C1C—C2C—C3C144.7 (3)
C12A—C13A—C14A—C9A1.7 (5)C1C—C2C—C3C—C3Ci66.6 (5)
C8AB—N1B—C2B—N2B177.7 (3)O2D—C1D—C2D—C3D58.8 (4)
C8AB—N1B—C2B—N3B1.1 (5)O1D—C1D—C2D—C3D121.4 (3)
N2B—C2B—N3B—C4B178.2 (3)C1D—C2D—C3D—C3Dii58.9 (5)
Symmetry codes: (i) x+1, y, z+1; (ii) x+1, y+1, z.
Triamterenium pimelate, DMSO solvate (1d_DMSO) top
Crystal data top
2(C12H12N7+)·C7H10O42·2(C2H6OS)Z = 4
Mr = 822.98F(000) = 1736
Triclinic, P1Dx = 1.402 Mg m3
a = 14.0750 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 14.8889 (6) ÅCell parameters from 59468 reflections
c = 19.635 (2) Åθ = 1.0–25.4°
α = 86.408 (2)°µ = 0.20 mm1
β = 88.142 (3)°T = 150 K
γ = 71.702 (2)°Block, colourless
V = 3898.7 (5) Å30.14 × 0.07 × 0.05 mm
Data collection top
Nonius Kappa CCD
diffractometer
13988 independent reflections
Radiation source: fine-focus sealed tube5187 reflections with I > 2σ(I)
None monochromatorRint = 0.114
Thin slice ω and φ scansθmax = 25.4°, θmin = 3.5°
Absorption correction: multi-scan
multi-scan from symmetry-related measurements Sortav (Blessing 1995)
h = 1616
Tmin = 0.932, Tmax = 1.000k = 1717
32837 measured reflectionsl = 1923
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.079Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.220H-atom parameters constrained
S = 0.95 w = 1/[σ2(Fo2) + (0.0923P)2]
where P = (Fo2 + 2Fc2)/3
13988 reflections(Δ/σ)max < 0.001
1035 parametersΔρmax = 0.78 e Å3
0 restraintsΔρmin = 0.38 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
N1A0.3412 (4)0.8401 (3)0.5162 (3)0.0348 (14)
H1XA0.31160.88270.50370.042*
C2A0.3044 (5)0.7509 (4)0.4949 (4)0.0357 (17)
N2A0.2276 (4)0.7330 (3)0.4508 (3)0.0466 (16)
H3A0.20170.67580.43590.056*
H2A0.20280.77840.43670.056*
N3A0.3411 (4)0.6802 (3)0.5158 (3)0.0367 (14)
C4A0.4226 (5)0.7003 (4)0.5571 (3)0.0310 (16)
N4A0.4587 (4)0.6328 (3)0.5781 (3)0.0397 (15)
H4A0.43000.57480.56540.048*
H5A0.51190.64530.60510.048*
C4AA0.4688 (5)0.7966 (4)0.5772 (3)0.0264 (15)
N5A0.5508 (4)0.8155 (3)0.6190 (3)0.0336 (14)
C6A0.5879 (4)0.9026 (4)0.6389 (3)0.0275 (15)
C7A0.5412 (5)0.9732 (4)0.6181 (3)0.0354 (17)
N7A0.5770 (4)1.0625 (3)0.6373 (3)0.0369 (14)
H7A0.54741.10440.62290.044*
H6A0.63021.07940.66410.044*
N8A0.4592 (4)0.9544 (3)0.5768 (3)0.0314 (13)
C8AA0.4245 (5)0.8638 (4)0.5574 (3)0.0297 (16)
C9A0.6754 (5)0.9193 (4)0.6869 (3)0.0328 (16)
C10A0.6843 (5)0.9702 (5)0.7456 (4)0.0458 (19)
H10A0.63500.99880.75530.055*
C11A0.7652 (5)0.9788 (5)0.7895 (4)0.0462 (19)
H11A0.77071.01260.82970.055*
C12A0.8379 (5)0.9388 (5)0.7754 (4)0.0441 (19)
H12A0.89390.94590.80530.053*
C13A0.8287 (5)0.8893 (4)0.7187 (4)0.046 (2)
H13A0.87890.86180.70910.055*
C14A0.7481 (5)0.8781 (4)0.6745 (4)0.0394 (18)
H14A0.74250.84200.63550.047*
N1B0.4818 (4)0.3749 (3)0.5968 (3)0.0306 (13)
H1XB0.51170.43260.60980.037*
C2B0.5172 (5)0.3033 (4)0.6201 (4)0.0358 (17)
N2B0.5934 (4)0.3226 (3)0.6615 (3)0.0412 (15)
H3B0.61860.27770.67630.049*
H2B0.62010.38060.67490.049*
N3B0.4776 (4)0.2141 (3)0.6003 (3)0.0325 (14)
C4B0.3954 (5)0.1948 (4)0.5588 (3)0.0324 (16)
N4B0.3550 (4)0.1049 (3)0.5415 (3)0.0388 (15)
H4B0.38170.06140.55700.047*
H5B0.30170.08930.51470.047*
C4AB0.3543 (5)0.2669 (4)0.5339 (3)0.0302 (16)
N5B0.2743 (4)0.2478 (3)0.4906 (3)0.0337 (14)
C6B0.2421 (5)0.3175 (4)0.4661 (3)0.0321 (17)
C7B0.2912 (5)0.4134 (4)0.4898 (4)0.0355 (17)
N7B0.2563 (4)0.4843 (3)0.4689 (3)0.0426 (15)
H7B0.28500.54150.48330.051*
H6B0.20450.47390.44070.051*
N8B0.3685 (4)0.4317 (3)0.5318 (3)0.0339 (14)
C8AB0.4011 (5)0.3592 (4)0.5537 (3)0.0330 (17)
C9B0.1543 (5)0.2960 (4)0.4203 (4)0.0338 (17)
C10B0.1504 (5)0.3476 (4)0.3590 (4)0.0399 (18)
H10B0.20520.40180.34660.048*
C11B0.0680 (6)0.3207 (5)0.3164 (4)0.048 (2)
H11B0.06710.35490.27400.058*
C12B0.0146 (5)0.2428 (5)0.3356 (4)0.047 (2)
H12B0.07210.22530.30670.057*
C13B0.0126 (5)0.1917 (5)0.3964 (4)0.050 (2)
H13B0.06840.13910.41000.060*
C14B0.0719 (5)0.2186 (4)0.4367 (4)0.0455 (19)
H14B0.07390.18220.47790.055*
N1C0.1600 (4)0.3410 (3)1.0223 (3)0.0340 (14)
H1XC0.18970.38131.01010.041*
C2C0.1966 (5)0.2463 (4)1.0008 (4)0.0341 (17)
N3C0.1615 (4)0.1796 (3)1.0245 (3)0.0308 (13)
C4C0.0824 (5)0.2078 (4)1.0657 (3)0.0288 (16)
C4AC0.0387 (4)0.3056 (4)1.0856 (3)0.0257 (15)
N5C0.0442 (4)0.3334 (3)1.1269 (3)0.0310 (13)
N8C0.0421 (4)0.4642 (3)1.0801 (3)0.0329 (14)
N2C0.2714 (4)0.2207 (3)0.9584 (3)0.0390 (15)
H3C0.29830.16050.94560.047*
H2C0.29480.26360.94280.047*
N4C0.0470 (3)0.1418 (3)1.0879 (3)0.0333 (14)
H4C0.07560.08181.07540.040*
H5C0.00490.15831.11500.040*
C6C0.0848 (5)0.4239 (4)1.1436 (4)0.0340 (17)
C7C0.0415 (5)0.4916 (4)1.1194 (3)0.0325 (17)
N7C0.0809 (4)0.5850 (3)1.1341 (3)0.0397 (15)
H7C0.05290.62471.11860.048*
H6C0.13490.60661.15920.048*
C8AC0.0775 (5)0.3716 (4)1.0627 (3)0.0282 (16)
C9C0.1727 (4)0.4482 (4)1.1883 (3)0.0294 (16)
C10C0.1915 (5)0.5145 (4)1.2426 (3)0.0337 (17)
H10C0.14690.55051.25130.040*
C11C0.2719 (5)0.5305 (4)1.2848 (4)0.047 (2)
H11C0.28320.57791.32100.056*
C12C0.3358 (5)0.4775 (4)1.2741 (4)0.0428 (19)
H12C0.39090.48731.30350.051*
C13C0.3197 (5)0.4098 (5)1.2205 (4)0.0433 (19)
H13C0.36430.37351.21310.052*
C14C0.2398 (5)0.3944 (4)1.1777 (4)0.0398 (18)
H14C0.22950.34781.14110.048*
N1D0.0121 (4)1.1122 (3)0.0888 (3)0.0339 (14)
H1XD0.01931.05270.10100.041*
C2D0.0204 (5)1.1828 (4)0.1105 (3)0.0316 (16)
N3D0.0186 (4)1.2739 (3)0.0912 (3)0.0322 (13)
C4D0.1013 (5)1.2998 (4)0.0524 (4)0.0336 (17)
C4AD0.1423 (5)1.2300 (4)0.0287 (3)0.0316 (17)
N5D0.2240 (4)1.2551 (3)0.0111 (3)0.0304 (13)
N8D0.1265 (4)1.0640 (3)0.0302 (3)0.0314 (13)
N2D0.0988 (4)1.1575 (3)0.1512 (3)0.0435 (16)
H3D0.12381.20060.16480.052*
H2D0.12591.09760.16480.052*
N4D0.1433 (4)1.3907 (3)0.0353 (3)0.0383 (15)
H4D0.11731.43290.04920.046*
H5D0.19721.40900.01000.046*
C6D0.2568 (5)1.1878 (4)0.0329 (3)0.0325 (17)
C7D0.2067 (5)1.0895 (4)0.0110 (3)0.0309 (16)
N7D0.2411 (4)1.0201 (3)0.0289 (3)0.0403 (15)
H7D0.21160.96130.01380.048*
H6D0.29321.03340.05570.048*
C8AD0.0938 (5)1.1349 (4)0.0479 (3)0.0289 (16)
C9D0.3464 (4)1.2154 (4)0.0752 (3)0.0294 (16)
C10D0.3522 (5)1.1746 (4)0.1362 (4)0.0382 (18)
H10D0.29741.12320.15060.046*
C11D0.4368 (5)1.2077 (5)0.1761 (4)0.046 (2)
H11D0.43851.18050.21830.056*
C12D0.5191 (5)1.2802 (4)0.1547 (4)0.048 (2)
H12D0.57711.30310.18210.058*
C13D0.5157 (5)1.3191 (4)0.0926 (4)0.0425 (19)
H13D0.57271.36650.07620.051*
C14D0.4299 (5)1.2887 (4)0.0553 (4)0.0425 (19)
H14D0.42721.31870.01440.051*
C1E0.1644 (5)0.9261 (5)0.4352 (4)0.0391 (18)
O1E0.2218 (3)0.9506 (3)0.4850 (3)0.0446 (13)
C2E0.0719 (5)0.9576 (4)0.4282 (4)0.0420 (19)
H2E0.04170.95320.47360.050*
H3E0.09121.02470.41080.050*
O2E0.1816 (4)0.8777 (3)0.3887 (3)0.0610 (15)
C3E0.0071 (6)0.8951 (5)0.3784 (4)0.064 (2)
H4E0.02390.82810.39570.077*
H5E0.02410.90040.33330.077*
O3E0.0701 (3)0.9369 (3)0.1547 (3)0.0398 (12)
C4E0.1008 (5)0.9191 (5)0.3691 (4)0.058 (2)
H6E0.13020.91870.41430.070*
H7E0.08580.98380.34750.070*
O4E0.1642 (3)0.9899 (3)0.2207 (2)0.0482 (13)
C5E0.1772 (5)0.8490 (5)0.3245 (4)0.0471 (19)
H8E0.19560.78550.34850.056*
H9E0.23850.86820.32020.056*
C6E0.1421 (5)0.8406 (4)0.2524 (4)0.0381 (18)
H10E0.19380.78900.23020.046*
H11E0.08010.82250.25650.046*
C7E0.1220 (5)0.9302 (4)0.2070 (4)0.0400 (18)
C1F0.3368 (5)0.4101 (5)0.9330 (4)0.0351 (17)
O1F0.2759 (3)0.4460 (3)0.9793 (3)0.0418 (12)
C2F0.4241 (5)0.4484 (4)0.9249 (4)0.0374 (18)
H2F0.39720.51430.91060.045*
H3F0.45720.45030.97000.045*
O2F0.3333 (3)0.3420 (3)0.8923 (2)0.0465 (13)
C3F0.5020 (5)0.3923 (4)0.8742 (4)0.0411 (18)
H4F0.46940.39240.82880.049*
H5F0.52700.32580.88750.049*
O3F0.6513 (3)0.5169 (3)0.7339 (2)0.0472 (13)
C4F0.5922 (4)0.4288 (4)0.8680 (4)0.0373 (18)
H6F0.56840.49360.85140.045*
H7F0.62290.43230.91370.045*
O4F0.5715 (3)0.4564 (3)0.6518 (3)0.0422 (12)
C5F0.6714 (5)0.3661 (4)0.8196 (4)0.046 (2)
H8F0.69330.30090.83570.056*
H9F0.73030.38910.82220.056*
C6F0.6378 (5)0.3622 (4)0.7449 (3)0.0364 (17)
H10F0.68970.31120.71990.044*
H11F0.57570.34420.74290.044*
C7F0.6184 (5)0.4527 (5)0.7079 (4)0.0405 (18)
C1G0.0578 (6)0.6091 (5)0.3990 (4)0.065 (2)
H1G0.02030.67200.37940.097*
H2G0.12750.59230.38290.097*
H3G0.05570.61000.44890.097*
O1G0.0955 (3)0.5463 (3)0.4094 (2)0.0459 (13)
S1G0.00322 (13)0.52427 (12)0.37339 (10)0.0442 (5)
C2G0.0826 (5)0.4230 (4)0.4187 (4)0.056 (2)
H4G0.07800.43360.46760.085*
H5G0.15180.41170.40270.085*
H6G0.06170.36760.41070.085*
C1H0.5350 (5)0.1169 (5)0.0853 (4)0.058 (2)
H4H0.48610.17830.09470.086*
H5H0.59930.11230.10550.086*
H6H0.54370.11140.03580.086*
O1H0.4029 (3)0.0265 (3)0.0795 (2)0.0442 (13)
S1H0.49107 (13)0.02327 (11)0.12155 (10)0.0412 (5)
C2H0.5922 (5)0.0725 (4)0.0929 (4)0.0462 (19)
H1H0.60540.06080.04440.069*
H2H0.65200.07820.11920.069*
H3H0.57490.13130.09930.069*
C1I0.3932 (5)0.2297 (5)0.2514 (4)0.062 (2)
H1I0.39290.28760.22470.092*
H2I0.46020.18320.24950.092*
H3I0.37500.24440.29890.092*
O1I0.2039 (3)0.2564 (3)0.2261 (2)0.0424 (12)
S1I0.30583 (14)0.18230 (12)0.21719 (11)0.0510 (6)
C2I0.3110 (6)0.0922 (5)0.2821 (4)0.068 (2)
H4I0.28780.12130.32550.101*
H5I0.38000.05030.28660.101*
H6I0.26780.05540.26990.101*
C1J0.8105 (5)0.6263 (4)0.2340 (4)0.058 (2)
H1J0.81040.61290.28350.087*
H2J0.87710.59460.21520.087*
H3J0.76110.60290.21330.087*
O1J0.6869 (3)0.7982 (3)0.2582 (2)0.0478 (13)
S1J0.77936 (14)0.75168 (12)0.21593 (11)0.0504 (6)
C2J0.8801 (5)0.7683 (5)0.2584 (4)0.060 (2)
H4J0.87340.83590.25640.091*
H5J0.94310.73330.23620.091*
H6J0.87980.74480.30610.091*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.032 (3)0.027 (3)0.047 (4)0.012 (3)0.003 (3)0.001 (3)
C2A0.032 (4)0.034 (4)0.040 (5)0.006 (3)0.005 (4)0.013 (3)
N2A0.036 (4)0.026 (3)0.077 (5)0.008 (3)0.009 (4)0.010 (3)
N3A0.036 (3)0.023 (3)0.052 (4)0.010 (3)0.002 (3)0.006 (3)
C4A0.027 (4)0.031 (4)0.034 (5)0.008 (3)0.001 (4)0.004 (3)
N4A0.040 (3)0.020 (3)0.061 (4)0.012 (3)0.008 (3)0.004 (3)
C4AA0.033 (4)0.018 (3)0.028 (4)0.009 (3)0.005 (3)0.003 (3)
N5A0.033 (3)0.028 (3)0.039 (4)0.009 (3)0.001 (3)0.002 (3)
C6A0.029 (4)0.024 (3)0.030 (4)0.008 (3)0.001 (3)0.002 (3)
C7A0.043 (5)0.030 (4)0.033 (5)0.012 (3)0.002 (4)0.001 (3)
N7A0.042 (3)0.016 (3)0.051 (4)0.008 (3)0.015 (3)0.007 (3)
N8A0.040 (4)0.014 (3)0.036 (4)0.003 (2)0.003 (3)0.005 (2)
C8AA0.023 (4)0.038 (4)0.025 (4)0.005 (3)0.004 (3)0.002 (3)
C9A0.029 (4)0.028 (3)0.035 (5)0.000 (3)0.001 (3)0.005 (3)
C10A0.040 (5)0.052 (4)0.051 (6)0.022 (4)0.001 (4)0.002 (4)
C11A0.044 (5)0.052 (4)0.038 (5)0.007 (4)0.009 (4)0.010 (4)
C12A0.045 (5)0.044 (4)0.044 (5)0.017 (4)0.009 (4)0.001 (4)
C13A0.039 (5)0.030 (4)0.063 (6)0.006 (3)0.001 (4)0.008 (4)
C14A0.027 (4)0.042 (4)0.051 (5)0.013 (3)0.006 (4)0.002 (3)
N1B0.030 (3)0.013 (3)0.045 (4)0.001 (2)0.005 (3)0.004 (2)
C2B0.035 (4)0.041 (4)0.039 (5)0.021 (4)0.001 (4)0.006 (3)
N2B0.041 (4)0.025 (3)0.057 (4)0.009 (3)0.010 (3)0.008 (3)
N3B0.034 (3)0.019 (3)0.045 (4)0.009 (2)0.007 (3)0.007 (3)
C4B0.028 (4)0.038 (4)0.032 (5)0.011 (3)0.010 (4)0.003 (3)
N4B0.039 (3)0.023 (3)0.057 (4)0.013 (3)0.007 (3)0.009 (3)
C4AB0.037 (4)0.021 (3)0.033 (5)0.011 (3)0.003 (4)0.002 (3)
N5B0.026 (3)0.028 (3)0.047 (4)0.008 (2)0.002 (3)0.005 (3)
C6B0.035 (4)0.025 (4)0.035 (5)0.008 (3)0.009 (4)0.000 (3)
C7B0.037 (4)0.024 (4)0.047 (5)0.011 (3)0.002 (4)0.001 (3)
N7B0.041 (4)0.037 (3)0.057 (4)0.022 (3)0.015 (3)0.013 (3)
N8B0.028 (3)0.025 (3)0.050 (4)0.011 (2)0.006 (3)0.007 (3)
C8AB0.033 (4)0.024 (4)0.041 (5)0.008 (3)0.003 (4)0.001 (3)
C9B0.034 (4)0.027 (4)0.042 (5)0.013 (3)0.004 (4)0.005 (3)
C10B0.039 (5)0.029 (4)0.052 (6)0.012 (3)0.012 (4)0.007 (4)
C11B0.060 (6)0.062 (5)0.032 (5)0.033 (5)0.003 (4)0.005 (4)
C12B0.043 (5)0.044 (4)0.058 (6)0.014 (4)0.009 (4)0.018 (4)
C13B0.039 (5)0.044 (4)0.069 (7)0.014 (4)0.015 (5)0.008 (4)
C14B0.044 (5)0.035 (4)0.058 (6)0.013 (4)0.009 (4)0.001 (4)
N1C0.040 (4)0.025 (3)0.039 (4)0.012 (3)0.003 (3)0.004 (3)
C2C0.031 (4)0.031 (4)0.035 (5)0.002 (3)0.003 (4)0.002 (3)
N3C0.036 (3)0.023 (3)0.036 (4)0.013 (3)0.001 (3)0.005 (2)
C4C0.028 (4)0.032 (4)0.026 (4)0.008 (3)0.003 (3)0.004 (3)
C4AC0.022 (4)0.021 (3)0.034 (4)0.006 (3)0.002 (3)0.001 (3)
N5C0.035 (3)0.024 (3)0.034 (4)0.010 (3)0.007 (3)0.006 (2)
N8C0.033 (3)0.023 (3)0.042 (4)0.009 (3)0.000 (3)0.004 (3)
N2C0.036 (3)0.033 (3)0.048 (4)0.012 (3)0.012 (3)0.001 (3)
N4C0.030 (3)0.017 (3)0.052 (4)0.006 (2)0.011 (3)0.002 (2)
C6C0.026 (4)0.026 (4)0.051 (5)0.011 (3)0.006 (4)0.001 (3)
C7C0.027 (4)0.023 (4)0.044 (5)0.004 (3)0.002 (4)0.002 (3)
N7C0.039 (3)0.028 (3)0.053 (4)0.010 (3)0.016 (3)0.001 (3)
C8AC0.029 (4)0.020 (3)0.033 (5)0.005 (3)0.001 (3)0.002 (3)
C9C0.024 (4)0.024 (3)0.038 (5)0.002 (3)0.000 (3)0.007 (3)
C10C0.033 (4)0.035 (4)0.036 (5)0.013 (3)0.003 (4)0.001 (3)
C11C0.044 (5)0.039 (4)0.051 (6)0.001 (4)0.003 (4)0.013 (4)
C12C0.034 (4)0.045 (4)0.052 (6)0.015 (4)0.015 (4)0.002 (4)
C13C0.037 (5)0.047 (4)0.046 (5)0.013 (4)0.003 (4)0.005 (4)
C14C0.028 (4)0.030 (4)0.060 (6)0.007 (3)0.000 (4)0.000 (3)
N1D0.033 (3)0.019 (3)0.049 (4)0.005 (2)0.009 (3)0.004 (3)
C2D0.023 (4)0.035 (4)0.036 (5)0.008 (3)0.001 (4)0.001 (3)
N3D0.032 (3)0.021 (3)0.044 (4)0.009 (3)0.000 (3)0.002 (3)
C4D0.036 (4)0.016 (3)0.048 (5)0.008 (3)0.003 (4)0.000 (3)
C4AD0.031 (4)0.021 (3)0.046 (5)0.013 (3)0.001 (4)0.001 (3)
N5D0.028 (3)0.023 (3)0.040 (4)0.009 (2)0.002 (3)0.001 (2)
N8D0.023 (3)0.024 (3)0.045 (4)0.003 (2)0.003 (3)0.004 (3)
N2D0.033 (4)0.028 (3)0.069 (5)0.008 (3)0.005 (3)0.004 (3)
N4D0.032 (3)0.028 (3)0.058 (4)0.014 (3)0.002 (3)0.004 (3)
C6D0.033 (4)0.023 (3)0.043 (5)0.011 (3)0.005 (4)0.002 (3)
C7D0.031 (4)0.018 (3)0.042 (5)0.006 (3)0.002 (4)0.002 (3)
N7D0.039 (3)0.031 (3)0.053 (4)0.015 (3)0.003 (3)0.001 (3)
C8AD0.032 (4)0.018 (3)0.036 (5)0.007 (3)0.002 (4)0.003 (3)
C9D0.027 (4)0.026 (3)0.037 (5)0.010 (3)0.001 (3)0.004 (3)
C10D0.025 (4)0.024 (3)0.064 (6)0.007 (3)0.003 (4)0.005 (4)
C11D0.048 (5)0.043 (4)0.055 (6)0.023 (4)0.005 (4)0.003 (4)
C12D0.041 (5)0.034 (4)0.069 (6)0.012 (4)0.014 (4)0.005 (4)
C13D0.024 (4)0.039 (4)0.061 (6)0.005 (3)0.003 (4)0.002 (4)
C14D0.045 (5)0.028 (4)0.053 (5)0.009 (4)0.004 (4)0.000 (3)
C1E0.043 (5)0.033 (4)0.042 (5)0.015 (4)0.007 (4)0.002 (4)
O1E0.040 (3)0.036 (3)0.058 (4)0.012 (2)0.015 (3)0.012 (2)
C2E0.033 (4)0.039 (4)0.054 (5)0.010 (3)0.003 (4)0.004 (4)
O2E0.078 (4)0.054 (3)0.060 (4)0.034 (3)0.024 (3)0.020 (3)
C3E0.057 (5)0.057 (5)0.083 (7)0.026 (4)0.016 (5)0.016 (5)
O3E0.039 (3)0.030 (2)0.051 (4)0.011 (2)0.010 (3)0.001 (2)
C4E0.045 (5)0.071 (5)0.059 (6)0.018 (4)0.001 (4)0.003 (4)
O4E0.054 (3)0.033 (3)0.063 (4)0.019 (2)0.018 (3)0.002 (2)
C5E0.036 (4)0.054 (4)0.040 (5)0.001 (4)0.002 (4)0.003 (4)
C6E0.032 (4)0.027 (4)0.052 (6)0.006 (3)0.012 (4)0.001 (3)
C7E0.030 (4)0.035 (4)0.048 (6)0.002 (3)0.004 (4)0.002 (4)
C1F0.028 (4)0.032 (4)0.042 (5)0.004 (3)0.002 (4)0.004 (4)
O1F0.034 (3)0.030 (2)0.063 (4)0.011 (2)0.011 (3)0.001 (2)
C2F0.034 (4)0.027 (3)0.051 (5)0.008 (3)0.004 (4)0.006 (3)
O2F0.056 (3)0.040 (3)0.051 (4)0.027 (2)0.011 (3)0.007 (2)
C3F0.038 (4)0.041 (4)0.047 (5)0.016 (3)0.002 (4)0.006 (4)
O3F0.054 (3)0.035 (3)0.056 (4)0.021 (2)0.012 (3)0.004 (2)
C4F0.032 (4)0.036 (4)0.047 (5)0.017 (3)0.004 (4)0.002 (3)
O4F0.048 (3)0.039 (3)0.045 (4)0.021 (2)0.013 (3)0.008 (2)
C5F0.030 (4)0.047 (4)0.062 (6)0.009 (3)0.006 (4)0.011 (4)
C6F0.037 (4)0.035 (4)0.037 (5)0.010 (3)0.001 (4)0.002 (3)
C7F0.029 (4)0.040 (4)0.046 (6)0.001 (3)0.003 (4)0.004 (4)
C1G0.056 (5)0.064 (5)0.085 (7)0.034 (4)0.013 (5)0.012 (5)
O1G0.032 (3)0.039 (3)0.069 (4)0.013 (2)0.012 (3)0.014 (2)
S1G0.0386 (12)0.0427 (10)0.0491 (14)0.0097 (9)0.0037 (10)0.0056 (9)
C2G0.053 (5)0.050 (4)0.061 (6)0.007 (4)0.003 (4)0.011 (4)
C1H0.045 (5)0.053 (4)0.083 (7)0.025 (4)0.006 (4)0.004 (4)
O1H0.027 (3)0.036 (2)0.067 (4)0.007 (2)0.011 (3)0.005 (2)
S1H0.0378 (11)0.0345 (9)0.0498 (14)0.0092 (8)0.0018 (10)0.0020 (8)
C2H0.033 (4)0.033 (4)0.064 (6)0.002 (3)0.004 (4)0.008 (4)
C1I0.045 (5)0.076 (5)0.071 (7)0.031 (4)0.005 (4)0.007 (5)
O1I0.028 (3)0.035 (2)0.058 (4)0.001 (2)0.002 (2)0.003 (2)
S1I0.0438 (12)0.0482 (11)0.0595 (15)0.0112 (10)0.0074 (11)0.0049 (10)
C2I0.066 (6)0.062 (5)0.078 (7)0.028 (4)0.023 (5)0.021 (5)
C1J0.045 (5)0.028 (4)0.096 (7)0.006 (3)0.010 (5)0.001 (4)
O1J0.035 (3)0.042 (3)0.065 (4)0.011 (2)0.018 (3)0.008 (2)
S1J0.0460 (12)0.0443 (11)0.0618 (15)0.0159 (9)0.0030 (11)0.0032 (10)
C2J0.041 (5)0.055 (5)0.088 (7)0.016 (4)0.002 (5)0.017 (4)
Geometric parameters (Å, º) top
N1A—C2A1.353 (7)N3D—C4D1.350 (8)
N1A—C8AA1.366 (7)C4D—N4D1.322 (7)
N1A—H1XA0.8800C4D—C4AD1.444 (8)
C2A—N2A1.332 (8)C4AD—N5D1.351 (7)
C2A—N3A1.348 (7)C4AD—C8AD1.398 (8)
N2A—H3A0.8800N5D—C6D1.325 (7)
N2A—H2A0.8800N8D—C8AD1.346 (7)
N3A—C4A1.349 (7)N8D—C7D1.351 (7)
C4A—N4A1.302 (7)N2D—H3D0.8800
C4A—C4AA1.451 (8)N2D—H2D0.8800
N4A—H4A0.8800N4D—H4D0.8800
N4A—H5A0.8800N4D—H5D0.8800
C4AA—N5A1.359 (7)C6D—C7D1.455 (8)
C4AA—C8AA1.366 (8)C6D—C9D1.466 (8)
N5A—C6A1.317 (7)C7D—N7D1.339 (7)
C6A—C7A1.436 (8)N7D—H7D0.8800
C6A—C9A1.493 (8)N7D—H6D0.8800
C7A—N7A1.340 (7)C9D—C10D1.392 (9)
C7A—N8A1.355 (8)C9D—C14D1.395 (8)
N7A—H7A0.8800C10D—C11D1.384 (9)
N7A—H6A0.8800C10D—H10D0.9500
N8A—C8AA1.357 (7)C11D—C12D1.388 (9)
C9A—C14A1.383 (8)C11D—H11D0.9500
C9A—C10A1.400 (9)C12D—C13D1.390 (9)
C10A—C11A1.384 (9)C12D—H12D0.9500
C10A—H10A0.9500C13D—C14D1.368 (9)
C11A—C12A1.377 (9)C13D—H13D0.9500
C11A—H11A0.9500C14D—H14D0.9500
C12A—C13A1.355 (9)C1E—O1E1.246 (8)
C12A—H12A0.9500C1E—O2E1.271 (8)
C13A—C14A1.380 (9)C1E—C2E1.516 (8)
C13A—H13A0.9500C2E—C3E1.566 (9)
C14A—H14A0.9500C2E—H2E0.9900
N1B—C2B1.361 (7)C2E—H3E0.9900
N1B—C8AB1.362 (7)C3E—C4E1.474 (9)
N1B—H1XB0.8800C3E—H4E0.9900
C2B—N2B1.295 (8)C3E—H5E0.9900
C2B—N3B1.346 (7)O3E—C7E1.259 (8)
N2B—H3B0.8800C4E—C5E1.536 (9)
N2B—H2B0.8800C4E—H6E0.9900
N3B—C4B1.357 (8)C4E—H7E0.9900
C4B—N4B1.341 (7)O4E—C7E1.260 (7)
C4B—C4AB1.426 (8)C5E—C6E1.540 (9)
N4B—H4B0.8800C5E—H8E0.9900
N4B—H5B0.8800C5E—H9E0.9900
C4AB—N5B1.355 (7)C6E—C7E1.512 (9)
C4AB—C8AB1.400 (8)C6E—H10E0.9900
N5B—C6B1.316 (7)C6E—H11E0.9900
C6B—C9B1.468 (9)C1F—O1F1.245 (7)
C6B—C7B1.475 (8)C1F—O2F1.264 (7)
C7B—N8B1.312 (8)C1F—C2F1.525 (8)
C7B—N7B1.335 (7)C2F—C3F1.510 (8)
N7B—H7B0.8800C2F—H2F0.9900
N7B—H6B0.8800C2F—H3F0.9900
N8B—C8AB1.343 (7)C3F—C4F1.541 (8)
C9B—C14B1.385 (9)C3F—H4F0.9900
C9B—C10B1.396 (9)C3F—H5F0.9900
C10B—C11B1.375 (9)O3F—C7F1.261 (8)
C10B—H10B0.9500C4F—C5F1.523 (9)
C11B—C12B1.402 (9)C4F—H6F0.9900
C11B—H11B0.9500C4F—H7F0.9900
C12B—C13B1.378 (10)O4F—C7F1.261 (8)
C12B—H12B0.9500C5F—C6F1.530 (9)
C13B—C14B1.371 (9)C5F—H8F0.9900
C13B—H13B0.9500C5F—H9F0.9900
C14B—H14B0.9500C6F—C7F1.516 (8)
N1C—C8AC1.367 (7)C6F—H10F0.9900
N1C—C2C1.384 (7)C6F—H11F0.9900
N1C—H1XC0.8800C1G—S1G1.776 (7)
C2C—N2C1.308 (8)C1G—H1G0.9800
C2C—N3C1.352 (7)C1G—H2G0.9800
N3C—C4C1.339 (7)C1G—H3G0.9800
C4C—N4C1.333 (7)O1G—S1G1.489 (4)
C4C—C4AC1.427 (8)S1G—C2G1.776 (7)
C4AC—C8AC1.369 (7)C2G—H4G0.9800
C4AC—N5C1.381 (7)C2G—H5G0.9800
N5C—C6C1.312 (7)C2G—H6G0.9800
N8C—C8AC1.336 (7)C1H—S1H1.796 (7)
N8C—C7C1.365 (8)C1H—H4H0.9800
N2C—H3C0.8800C1H—H5H0.9800
N2C—H2C0.8800C1H—H6H0.9800
N4C—H4C0.8800O1H—S1H1.499 (4)
N4C—H5C0.8800S1H—C2H1.775 (6)
C6C—C7C1.442 (8)C2H—H1H0.9800
C6C—C9C1.477 (9)C2H—H2H0.9800
C7C—N7C1.343 (7)C2H—H3H0.9800
N7C—H7C0.8800C1I—S1I1.766 (7)
N7C—H6C0.8800C1I—H1I0.9800
C9C—C10C1.380 (8)C1I—H2I0.9800
C9C—C14C1.420 (8)C1I—H3I0.9800
C10C—C11C1.374 (9)O1I—S1I1.523 (4)
C10C—H10C0.9500S1I—C2I1.777 (7)
C11C—C12C1.374 (9)C2I—H4I0.9800
C11C—H11C0.9500C2I—H5I0.9800
C12C—C13C1.383 (9)C2I—H6I0.9800
C12C—H12C0.9500C1J—S1J1.793 (6)
C13C—C14C1.379 (9)C1J—H1J0.9800
C13C—H13C0.9500C1J—H2J0.9800
C14C—H14C0.9500C1J—H3J0.9800
N1D—C8AD1.365 (7)O1J—S1J1.515 (4)
N1D—C2D1.366 (7)S1J—C2J1.757 (7)
N1D—H1XD0.8800C2J—H4J0.9800
C2D—N2D1.327 (7)C2J—H5J0.9800
C2D—N3D1.329 (7)C2J—H6J0.9800
C2A—N1A—C8AA119.6 (5)C2D—N2D—H3D120.0
C2A—N1A—H1XA120.2C2D—N2D—H2D120.0
C8AA—N1A—H1XA120.2H3D—N2D—H2D120.0
N2A—C2A—N3A118.8 (6)C4D—N4D—H4D120.0
N2A—C2A—N1A117.5 (6)C4D—N4D—H5D120.0
N3A—C2A—N1A123.7 (6)H4D—N4D—H5D120.0
C2A—N2A—H3A120.0N5D—C6D—C7D119.3 (6)
C2A—N2A—H2A120.0N5D—C6D—C9D118.8 (5)
H3A—N2A—H2A120.0C7D—C6D—C9D121.8 (5)
C2A—N3A—C4A118.4 (5)N7D—C7D—N8D116.8 (5)
N4A—C4A—N3A119.3 (5)N7D—C7D—C6D121.0 (6)
N4A—C4A—C4AA121.0 (6)N8D—C7D—C6D122.2 (5)
N3A—C4A—C4AA119.7 (5)C7D—N7D—H7D120.0
C4A—N4A—H4A120.0C7D—N7D—H6D120.0
C4A—N4A—H5A120.0H7D—N7D—H6D120.0
H4A—N4A—H5A120.0N8D—C8AD—N1D117.7 (5)
N5A—C4AA—C8AA122.2 (5)N8D—C8AD—C4AD122.9 (6)
N5A—C4AA—C4A118.8 (5)N1D—C8AD—C4AD119.3 (5)
C8AA—C4AA—C4A118.8 (6)C10D—C9D—C14D117.3 (6)
C6A—N5A—C4AA117.2 (5)C10D—C9D—C6D123.7 (6)
N5A—C6A—C7A120.6 (6)C14D—C9D—C6D119.0 (6)
N5A—C6A—C9A115.4 (5)C11D—C10D—C9D120.9 (6)
C7A—C6A—C9A123.9 (5)C11D—C10D—H10D119.5
N7A—C7A—N8A115.5 (5)C9D—C10D—H10D119.5
N7A—C7A—C6A122.2 (6)C10D—C11D—C12D120.4 (7)
N8A—C7A—C6A122.3 (5)C10D—C11D—H11D119.8
C7A—N7A—H7A120.0C12D—C11D—H11D119.8
C7A—N7A—H6A120.0C11D—C12D—C13D119.1 (7)
H7A—N7A—H6A120.0C11D—C12D—H12D120.4
C7A—N8A—C8AA114.6 (5)C13D—C12D—H12D120.4
N8A—C8AA—N1A117.4 (5)C14D—C13D—C12D119.7 (7)
N8A—C8AA—C4AA123.1 (6)C14D—C13D—H13D120.1
N1A—C8AA—C4AA119.5 (5)C12D—C13D—H13D120.1
C14A—C9A—C10A118.8 (6)C13D—C14D—C9D122.3 (7)
C14A—C9A—C6A118.2 (6)C13D—C14D—H14D118.9
C10A—C9A—C6A123.0 (6)C9D—C14D—H14D118.9
C11A—C10A—C9A119.7 (6)O1E—C1E—O2E122.7 (6)
C11A—C10A—H10A120.1O1E—C1E—C2E118.9 (6)
C9A—C10A—H10A120.1O2E—C1E—C2E118.4 (7)
C12A—C11A—C10A120.6 (7)C1E—C2E—C3E111.3 (6)
C12A—C11A—H11A119.7C1E—C2E—H2E109.4
C10A—C11A—H11A119.7C3E—C2E—H2E109.4
C13A—C12A—C11A119.5 (7)C1E—C2E—H3E109.4
C13A—C12A—H12A120.3C3E—C2E—H3E109.4
C11A—C12A—H12A120.3H2E—C2E—H3E108.0
C12A—C13A—C14A121.4 (7)C4E—C3E—C2E115.5 (6)
C12A—C13A—H13A119.3C4E—C3E—H4E108.4
C14A—C13A—H13A119.3C2E—C3E—H4E108.4
C13A—C14A—C9A120.1 (7)C4E—C3E—H5E108.4
C13A—C14A—H14A120.0C2E—C3E—H5E108.4
C9A—C14A—H14A120.0H4E—C3E—H5E107.5
C2B—N1B—C8AB121.4 (5)C3E—C4E—C5E111.8 (6)
C2B—N1B—H1XB119.3C3E—C4E—H6E109.2
C8AB—N1B—H1XB119.3C5E—C4E—H6E109.2
N2B—C2B—N3B119.0 (6)C3E—C4E—H7E109.2
N2B—C2B—N1B118.5 (6)C5E—C4E—H7E109.2
N3B—C2B—N1B122.5 (6)H6E—C4E—H7E107.9
C2B—N2B—H3B120.0C4E—C5E—C6E115.6 (6)
C2B—N2B—H2B120.0C4E—C5E—H8E108.4
H3B—N2B—H2B120.0C6E—C5E—H8E108.4
C2B—N3B—C4B117.9 (5)C4E—C5E—H9E108.4
N4B—C4B—N3B117.1 (5)C6E—C5E—H9E108.4
N4B—C4B—C4AB121.2 (6)H8E—C5E—H9E107.4
N3B—C4B—C4AB121.7 (6)C7E—C6E—C5E114.3 (6)
C4B—N4B—H4B120.0C7E—C6E—H10E108.7
C4B—N4B—H5B120.0C5E—C6E—H10E108.7
H4B—N4B—H5B120.0C7E—C6E—H11E108.7
N5B—C4AB—C8AB120.6 (5)C5E—C6E—H11E108.7
N5B—C4AB—C4B121.5 (5)H10E—C6E—H11E107.6
C8AB—C4AB—C4B117.9 (6)O3E—C7E—O4E124.1 (6)
C6B—N5B—C4AB119.3 (5)O3E—C7E—C6E117.5 (6)
N5B—C6B—C9B119.0 (5)O4E—C7E—C6E118.2 (7)
N5B—C6B—C7B118.6 (6)O1F—C1F—O2F124.9 (6)
C9B—C6B—C7B122.3 (5)O1F—C1F—C2F118.6 (6)
N8B—C7B—N7B118.2 (5)O2F—C1F—C2F116.5 (6)
N8B—C7B—C6B121.9 (5)C3F—C2F—C1F115.1 (5)
N7B—C7B—C6B119.8 (6)C3F—C2F—H2F108.5
C7B—N7B—H7B120.0C1F—C2F—H2F108.5
C7B—N7B—H6B120.0C3F—C2F—H3F108.5
H7B—N7B—H6B120.0C1F—C2F—H3F108.5
C7B—N8B—C8AB117.5 (5)H2F—C2F—H3F107.5
N8B—C8AB—N1B119.7 (5)C2F—C3F—C4F115.1 (5)
N8B—C8AB—C4AB121.9 (6)C2F—C3F—H4F108.5
N1B—C8AB—C4AB118.4 (5)C4F—C3F—H4F108.5
C14B—C9B—C10B117.4 (6)C2F—C3F—H5F108.5
C14B—C9B—C6B119.1 (6)C4F—C3F—H5F108.5
C10B—C9B—C6B123.4 (6)H4F—C3F—H5F107.5
C11B—C10B—C9B120.7 (7)C5F—C4F—C3F112.9 (5)
C11B—C10B—H10B119.6C5F—C4F—H6F109.0
C9B—C10B—H10B119.6C3F—C4F—H6F109.0
C10B—C11B—C12B119.9 (7)C5F—C4F—H7F109.0
C10B—C11B—H11B120.1C3F—C4F—H7F109.0
C12B—C11B—H11B120.1H6F—C4F—H7F107.8
C13B—C12B—C11B120.3 (7)C4F—C5F—C6F115.0 (5)
C13B—C12B—H12B119.9C4F—C5F—H8F108.5
C11B—C12B—H12B119.9C6F—C5F—H8F108.5
C14B—C13B—C12B118.4 (7)C4F—C5F—H9F108.5
C14B—C13B—H13B120.8C6F—C5F—H9F108.5
C12B—C13B—H13B120.8H8F—C5F—H9F107.5
C13B—C14B—C9B123.3 (7)C7F—C6F—C5F116.1 (5)
C13B—C14B—H14B118.3C7F—C6F—H10F108.3
C9B—C14B—H14B118.3C5F—C6F—H10F108.3
C8AC—N1C—C2C119.6 (5)C7F—C6F—H11F108.3
C8AC—N1C—H1XC120.2C5F—C6F—H11F108.3
C2C—N1C—H1XC120.2H10F—C6F—H11F107.4
N2C—C2C—N3C119.3 (5)O4F—C7F—O3F125.1 (6)
N2C—C2C—N1C118.0 (6)O4F—C7F—C6F116.1 (6)
N3C—C2C—N1C122.6 (6)O3F—C7F—C6F118.8 (7)
C4C—N3C—C2C118.3 (5)S1G—C1G—H1G109.5
N4C—C4C—N3C118.1 (5)S1G—C1G—H2G109.5
N4C—C4C—C4AC121.5 (6)H1G—C1G—H2G109.5
N3C—C4C—C4AC120.5 (5)S1G—C1G—H3G109.5
C8AC—C4AC—N5C120.3 (5)H1G—C1G—H3G109.5
C8AC—C4AC—C4C120.2 (6)H2G—C1G—H3G109.5
N5C—C4AC—C4C119.5 (5)O1G—S1G—C2G105.5 (3)
C6C—N5C—C4AC118.8 (5)O1G—S1G—C1G105.5 (3)
C8AC—N8C—C7C115.6 (5)C2G—S1G—C1G98.3 (4)
C2C—N2C—H3C120.0S1G—C2G—H4G109.5
C2C—N2C—H2C120.0S1G—C2G—H5G109.5
H3C—N2C—H2C120.0H4G—C2G—H5G109.5
C4C—N4C—H4C120.0S1G—C2G—H6G109.5
C4C—N4C—H5C120.0H4G—C2G—H6G109.5
H4C—N4C—H5C120.0H5G—C2G—H6G109.5
N5C—C6C—C7C119.6 (6)S1H—C1H—H4H109.5
N5C—C6C—C9C115.8 (5)S1H—C1H—H5H109.5
C7C—C6C—C9C124.6 (5)H4H—C1H—H5H109.5
N7C—C7C—N8C116.2 (5)S1H—C1H—H6H109.5
N7C—C7C—C6C122.0 (6)H4H—C1H—H6H109.5
N8C—C7C—C6C121.8 (5)H5H—C1H—H6H109.5
C7C—N7C—H7C120.0O1H—S1H—C2H106.1 (3)
C7C—N7C—H6C120.0O1H—S1H—C1H105.2 (3)
H7C—N7C—H6C120.0C2H—S1H—C1H97.0 (3)
N8C—C8AC—N1C117.8 (5)S1H—C2H—H1H109.5
N8C—C8AC—C4AC123.8 (6)S1H—C2H—H2H109.5
N1C—C8AC—C4AC118.4 (5)H1H—C2H—H2H109.5
C10C—C9C—C14C117.0 (6)S1H—C2H—H3H109.5
C10C—C9C—C6C125.4 (6)H1H—C2H—H3H109.5
C14C—C9C—C6C117.5 (6)H2H—C2H—H3H109.5
C11C—C10C—C9C122.8 (6)S1I—C1I—H1I109.5
C11C—C10C—H10C118.6S1I—C1I—H2I109.5
C9C—C10C—H10C118.6H1I—C1I—H2I109.5
C10C—C11C—C12C119.5 (7)S1I—C1I—H3I109.5
C10C—C11C—H11C120.2H1I—C1I—H3I109.5
C12C—C11C—H11C120.2H2I—C1I—H3I109.5
C11C—C12C—C13C119.8 (7)O1I—S1I—C1I105.8 (3)
C11C—C12C—H12C120.1O1I—S1I—C2I105.3 (3)
C13C—C12C—H12C120.1C1I—S1I—C2I98.3 (4)
C14C—C13C—C12C120.7 (7)S1I—C2I—H4I109.5
C14C—C13C—H13C119.6S1I—C2I—H5I109.5
C12C—C13C—H13C119.6H4I—C2I—H5I109.5
C13C—C14C—C9C120.2 (6)S1I—C2I—H6I109.5
C13C—C14C—H14C119.9H4I—C2I—H6I109.5
C9C—C14C—H14C119.9H5I—C2I—H6I109.5
C8AD—N1D—C2D119.4 (5)S1J—C1J—H1J109.5
C8AD—N1D—H1XD120.3S1J—C1J—H2J109.5
C2D—N1D—H1XD120.3H1J—C1J—H2J109.5
N2D—C2D—N3D118.3 (5)S1J—C1J—H3J109.5
N2D—C2D—N1D117.3 (5)H1J—C1J—H3J109.5
N3D—C2D—N1D124.4 (6)H2J—C1J—H3J109.5
C2D—N3D—C4D118.0 (5)O1J—S1J—C2J105.8 (3)
N4D—C4D—N3D118.6 (5)O1J—S1J—C1J107.0 (3)
N4D—C4D—C4AD120.3 (6)C2J—S1J—C1J97.4 (4)
N3D—C4D—C4AD121.1 (5)S1J—C2J—H4J109.5
N5D—C4AD—C8AD120.9 (5)S1J—C2J—H5J109.5
N5D—C4AD—C4D121.5 (5)H4J—C2J—H5J109.5
C8AD—C4AD—C4D117.6 (6)S1J—C2J—H6J109.5
C6D—N5D—C4AD118.9 (5)H4J—C2J—H6J109.5
C8AD—N8D—C7D115.7 (5)H5J—C2J—H6J109.5
C8AA—N1A—C2A—N2A175.1 (6)N4C—C4C—C4AC—N5C2.2 (9)
C8AA—N1A—C2A—N3A4.9 (9)N3C—C4C—C4AC—N5C178.6 (6)
N2A—C2A—N3A—C4A176.0 (6)C8AC—C4AC—N5C—C6C0.2 (9)
N1A—C2A—N3A—C4A4.0 (10)C4C—C4AC—N5C—C6C178.6 (6)
C2A—N3A—C4A—N4A179.6 (6)C4AC—N5C—C6C—C7C0.9 (9)
C2A—N3A—C4A—C4AA0.6 (9)C4AC—N5C—C6C—C9C179.6 (6)
N4A—C4A—C4AA—N5A0.3 (9)C8AC—N8C—C7C—N7C176.5 (5)
N3A—C4A—C4AA—N5A179.9 (6)C8AC—N8C—C7C—C6C3.5 (9)
N4A—C4A—C4AA—C8AA175.9 (6)N5C—C6C—C7C—N7C179.0 (6)
N3A—C4A—C4AA—C8AA4.3 (9)C9C—C6C—C7C—N7C2.4 (10)
C8AA—C4AA—N5A—C6A1.3 (9)N5C—C6C—C7C—N8C1.0 (10)
C4A—C4AA—N5A—C6A176.8 (6)C9C—C6C—C7C—N8C177.6 (6)
C4AA—N5A—C6A—C7A1.4 (9)C7C—N8C—C8AC—N1C178.8 (6)
C4AA—N5A—C6A—C9A177.7 (5)C7C—N8C—C8AC—C4AC4.3 (9)
N5A—C6A—C7A—N7A179.8 (6)C2C—N1C—C8AC—N8C177.3 (5)
C9A—C6A—C7A—N7A4.3 (10)C2C—N1C—C8AC—C4AC5.6 (9)
N5A—C6A—C7A—N8A1.2 (9)N5C—C4AC—C8AC—N8C2.6 (9)
C9A—C6A—C7A—N8A177.1 (6)C4C—C4AC—C8AC—N8C178.6 (6)
N7A—C7A—N8A—C8AA179.4 (5)N5C—C4AC—C8AC—N1C179.5 (5)
C6A—C7A—N8A—C8AA0.7 (9)C4C—C4AC—C8AC—N1C1.8 (9)
C7A—N8A—C8AA—N1A179.3 (5)N5C—C6C—C9C—C10C138.6 (6)
C7A—N8A—C8AA—C4AA0.5 (9)C7C—C6C—C9C—C10C40.1 (10)
C2A—N1A—C8AA—N8A179.3 (6)N5C—C6C—C9C—C14C36.6 (8)
C2A—N1A—C8AA—C4AA0.9 (9)C7C—C6C—C9C—C14C144.8 (6)
N5A—C4AA—C8AA—N8A0.9 (10)C14C—C9C—C10C—C11C1.2 (9)
C4A—C4AA—C8AA—N8A176.4 (6)C6C—C9C—C10C—C11C176.3 (6)
N5A—C4AA—C8AA—N1A178.9 (6)C9C—C10C—C11C—C12C1.6 (10)
C4A—C4AA—C8AA—N1A3.4 (9)C10C—C11C—C12C—C13C1.1 (10)
N5A—C6A—C9A—C14A41.6 (8)C11C—C12C—C13C—C14C0.4 (10)
C7A—C6A—C9A—C14A142.3 (6)C12C—C13C—C14C—C9C0.0 (10)
N5A—C6A—C9A—C10A134.9 (6)C10C—C9C—C14C—C13C0.4 (9)
C7A—C6A—C9A—C10A41.2 (9)C6C—C9C—C14C—C13C175.9 (6)
C14A—C9A—C10A—C11A0.4 (10)C8AD—N1D—C2D—N2D178.7 (6)
C6A—C9A—C10A—C11A176.8 (6)C8AD—N1D—C2D—N3D4.4 (9)
C9A—C10A—C11A—C12A1.0 (10)N2D—C2D—N3D—C4D176.9 (6)
C10A—C11A—C12A—C13A1.2 (10)N1D—C2D—N3D—C4D6.2 (9)
C11A—C12A—C13A—C14A0.0 (10)C2D—N3D—C4D—N4D177.1 (6)
C12A—C13A—C14A—C9A1.3 (10)C2D—N3D—C4D—C4AD4.2 (9)
C10A—C9A—C14A—C13A1.5 (10)N4D—C4D—C4AD—N5D0.1 (10)
C6A—C9A—C14A—C13A178.1 (5)N3D—C4D—C4AD—N5D178.8 (6)
C8AB—N1B—C2B—N2B179.2 (6)N4D—C4D—C4AD—C8AD179.3 (6)
C8AB—N1B—C2B—N3B2.6 (9)N3D—C4D—C4AD—C8AD0.6 (9)
N2B—C2B—N3B—C4B177.6 (6)C8AD—C4AD—N5D—C6D1.1 (9)
N1B—C2B—N3B—C4B4.2 (9)C4D—C4AD—N5D—C6D178.2 (6)
C2B—N3B—C4B—N4B177.7 (6)C4AD—N5D—C6D—C7D2.6 (9)
C2B—N3B—C4B—C4AB3.0 (9)C4AD—N5D—C6D—C9D179.1 (6)
N4B—C4B—C4AB—N5B1.6 (9)C8AD—N8D—C7D—N7D179.5 (5)
N3B—C4B—C4AB—N5B177.7 (6)C8AD—N8D—C7D—C6D2.1 (9)
N4B—C4B—C4AB—C8AB179.5 (6)N5D—C6D—C7D—N7D176.3 (6)
N3B—C4B—C4AB—C8AB0.2 (9)C9D—C6D—C7D—N7D0.1 (9)
C8AB—C4AB—N5B—C6B1.4 (9)N5D—C6D—C7D—N8D0.9 (9)
C4B—C4AB—N5B—C6B176.5 (6)C9D—C6D—C7D—N8D177.4 (6)
C4AB—N5B—C6B—C9B178.8 (6)C7D—N8D—C8AD—N1D179.2 (6)
C4AB—N5B—C6B—C7B3.2 (9)C7D—N8D—C8AD—C4AD3.7 (9)
N5B—C6B—C7B—N8B3.2 (9)C2D—N1D—C8AD—N8D176.9 (5)
C9B—C6B—C7B—N8B178.6 (6)C2D—N1D—C8AD—C4AD0.4 (9)
N5B—C6B—C7B—N7B176.1 (6)N5D—C4AD—C8AD—N8D2.2 (10)
C9B—C6B—C7B—N7B0.7 (9)C4D—C4AD—C8AD—N8D178.4 (6)
N7B—C7B—N8B—C8AB178.3 (6)N5D—C4AD—C8AD—N1D179.3 (6)
C6B—C7B—N8B—C8AB0.9 (9)C4D—C4AD—C8AD—N1D1.3 (9)
C7B—N8B—C8AB—N1B179.2 (6)N5D—C6D—C9D—C10D131.4 (6)
C7B—N8B—C8AB—C4AB1.1 (9)C7D—C6D—C9D—C10D52.1 (9)
C2B—N1B—C8AB—N8B180.0 (6)N5D—C6D—C9D—C14D46.3 (9)
C2B—N1B—C8AB—C4AB0.4 (9)C7D—C6D—C9D—C14D130.2 (6)
N5B—C4AB—C8AB—N8B1.0 (10)C14D—C9D—C10D—C11D1.8 (9)
C4B—C4AB—C8AB—N8B178.9 (6)C6D—C9D—C10D—C11D175.9 (6)
N5B—C4AB—C8AB—N1B179.4 (6)C9D—C10D—C11D—C12D2.4 (10)
C4B—C4AB—C8AB—N1B1.4 (9)C10D—C11D—C12D—C13D0.2 (10)
N5B—C6B—C9B—C14B44.2 (9)C11D—C12D—C13D—C14D3.3 (10)
C7B—C6B—C9B—C14B131.2 (6)C12D—C13D—C14D—C9D3.9 (10)
N5B—C6B—C9B—C10B133.1 (6)C10D—C9D—C14D—C13D1.4 (9)
C7B—C6B—C9B—C10B51.5 (9)C6D—C9D—C14D—C13D179.2 (6)
C14B—C9B—C10B—C11B1.0 (9)O1E—C1E—C2E—C3E161.3 (6)
C6B—C9B—C10B—C11B176.3 (6)O2E—C1E—C2E—C3E20.6 (9)
C9B—C10B—C11B—C12B2.3 (9)C1E—C2E—C3E—C4E179.0 (6)
C10B—C11B—C12B—C13B1.6 (10)C2E—C3E—C4E—C5E175.1 (6)
C11B—C12B—C13B—C14B0.4 (10)C3E—C4E—C5E—C6E58.4 (8)
C12B—C13B—C14B—C9B1.8 (10)C4E—C5E—C6E—C7E64.4 (8)
C10B—C9B—C14B—C13B1.1 (10)C5E—C6E—C7E—O3E162.5 (6)
C6B—C9B—C14B—C13B178.5 (6)C5E—C6E—C7E—O4E22.8 (8)
C8AC—N1C—C2C—N2C175.4 (6)O1F—C1F—C2F—C3F171.8 (6)
C8AC—N1C—C2C—N3C7.9 (9)O2F—C1F—C2F—C3F6.7 (8)
N2C—C2C—N3C—C4C177.4 (6)C1F—C2F—C3F—C4F177.8 (5)
N1C—C2C—N3C—C4C6.0 (9)C2F—C3F—C4F—C5F176.3 (6)
C2C—N3C—C4C—N4C178.9 (5)C3F—C4F—C5F—C6F64.9 (7)
C2C—N3C—C4C—C4AC1.9 (9)C4F—C5F—C6F—C7F68.3 (7)
N4C—C4C—C4AC—C8AC179.1 (6)C5F—C6F—C7F—O4F165.8 (6)
N3C—C4C—C4AC—C8AC0.1 (9)C5F—C6F—C7F—O3F15.7 (9)
Triamterenium azelate, DMSO solvate (1e_DMSO) top
Crystal data top
2(C12H12N7+)·C9H14O42·2(C2H6OS)F(000) = 1800
Mr = 851.03Dx = 1.384 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.7107 Å
a = 15.0338 (3) ÅCell parameters from 13200 reflections
b = 11.5004 (2) Åθ = 1.0–25.4°
c = 24.3960 (6) ŵ = 0.20 mm1
β = 104.539 (1)°T = 180 K
V = 4082.87 (15) Å3Block, colourless
Z = 40.14 × 0.10 × 0.05 mm
Data collection top
Nonius Kappa CCD
diffractometer
7406 independent reflections
Radiation source: fine-focus sealed tube4611 reflections with I > 2σ(I)
None monochromatorRint = 0.047
Thin slice ω and φ scansθmax = 25.4°, θmin = 3.5°
Absorption correction: multi-scan
multi-scan from symmetry-related measurements Sortav (Blessing 1995)
h = 1817
Tmin = 0.932, Tmax = 0.997k = 1313
22149 measured reflectionsl = 2729
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.059Hydrogen site location: mixed
wR(F2) = 0.163H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.095P)2 + 0.204P]
where P = (Fo2 + 2Fc2)/3
7406 reflections(Δ/σ)max < 0.001
705 parametersΔρmax = 1.26 e Å3
0 restraintsΔρmin = 0.40 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
N1A0.00745 (17)0.6306 (2)0.03372 (11)0.0350 (6)
C2A0.0642 (2)0.6587 (2)0.01120 (12)0.0350 (7)
N2A0.0485 (2)0.7337 (3)0.03070 (12)0.0450 (7)
N3A0.14916 (16)0.6127 (2)0.03002 (10)0.0357 (6)
C4A0.16405 (19)0.5376 (2)0.07309 (12)0.0317 (7)
N4A0.24705 (18)0.4922 (2)0.09131 (12)0.0358 (6)
C4AA0.09218 (19)0.5057 (2)0.09875 (12)0.0328 (7)
N5A0.10906 (16)0.43285 (19)0.14390 (10)0.0327 (6)
C6A0.0409 (2)0.4052 (2)0.16608 (12)0.0332 (7)
C7A0.05082 (19)0.4500 (2)0.14116 (12)0.0318 (7)
N7A0.1221 (2)0.4141 (2)0.15987 (13)0.0402 (7)
N8A0.06718 (16)0.52609 (19)0.09838 (10)0.0335 (6)
C8AA0.0052 (2)0.5542 (2)0.07765 (12)0.0334 (7)
C9A0.06145 (19)0.3236 (2)0.21485 (12)0.0341 (7)
C10A0.0303 (2)0.3422 (3)0.26338 (14)0.0435 (8)
C11A0.0523 (2)0.2623 (3)0.30757 (15)0.0538 (9)
C12A0.1044 (2)0.1665 (3)0.30407 (15)0.0491 (9)
C13A0.1367 (2)0.1477 (3)0.25632 (15)0.0447 (8)
C14A0.1158 (2)0.2269 (3)0.21185 (14)0.0378 (7)
N1B0.52477 (17)0.4847 (2)0.11282 (10)0.0302 (6)
C2B0.61363 (19)0.4517 (2)0.13193 (12)0.0307 (7)
N2B0.6333 (2)0.3808 (2)0.17591 (12)0.0408 (7)
N3B0.68140 (15)0.48655 (19)0.10902 (10)0.0306 (5)
C4B0.66074 (19)0.5636 (2)0.06628 (12)0.0295 (6)
N4B0.72793 (18)0.5977 (2)0.04347 (11)0.0346 (6)
C4AB0.56957 (18)0.6097 (2)0.04682 (11)0.0277 (6)
N5B0.55136 (15)0.69763 (19)0.00862 (9)0.0299 (5)
C6B0.46703 (19)0.7379 (2)0.00669 (11)0.0298 (6)
C7B0.39429 (19)0.6841 (2)0.01374 (11)0.0287 (6)
N7B0.30704 (18)0.7141 (2)0.00632 (12)0.0362 (6)
C8AB0.50110 (19)0.5661 (2)0.07066 (11)0.0272 (6)
N8B0.41325 (15)0.59965 (18)0.05340 (9)0.0290 (5)
C9B0.45030 (19)0.8408 (2)0.04485 (12)0.0319 (7)
C10B0.3980 (2)0.9345 (3)0.03473 (14)0.0370 (7)
C11B0.3890 (2)1.0330 (3)0.06838 (15)0.0419 (8)
C12B0.4318 (2)1.0388 (3)0.11232 (17)0.0535 (10)
C13B0.4837 (2)0.9462 (3)0.12258 (15)0.0501 (9)
C14B0.4939 (2)0.8480 (3)0.08887 (13)0.0389 (7)
C1C0.4328 (2)0.3134 (3)0.20478 (14)0.0452 (8)
O1C0.40424 (14)0.36829 (18)0.15868 (9)0.0432 (5)
C2C0.3673 (3)0.2281 (4)0.22178 (15)0.0610 (10)
H2C0.38230.14870.21120.073*
H3C0.30400.24610.19990.073*
O2C0.51231 (16)0.3203 (2)0.23588 (10)0.0606 (7)
C3C0.3702 (3)0.2296 (3)0.28510 (15)0.0480 (9)
O3C0.33111 (14)0.75697 (19)0.49178 (9)0.0485 (6)
C4C0.3350 (3)0.3422 (3)0.3024 (2)0.0611 (11)
O4C0.3859 (2)0.6685 (3)0.42795 (16)0.1124 (14)
C5C0.3189 (3)0.3418 (4)0.3603 (2)0.0738 (14)
C6C0.2745 (4)0.4656 (4)0.3675 (2)0.0847 (14)
C7C0.2583 (4)0.4816 (4)0.4202 (3)0.106 (2)
H12C0.31150.44960.44870.127*
H13C0.20410.43420.42180.127*
C8C0.2415 (3)0.6058 (3)0.43845 (19)0.0547 (10)
C9C0.3257 (2)0.6815 (3)0.45415 (15)0.0468 (8)
C1D0.7034 (4)0.0981 (4)0.2403 (2)0.0705 (13)
O1D0.80316 (15)0.28768 (17)0.24377 (9)0.0467 (6)
S1D0.78812 (6)0.19277 (7)0.28283 (4)0.0441 (2)
C2D0.7163 (3)0.2526 (4)0.32355 (18)0.0558 (10)
C1E0.5638 (5)0.4602 (5)0.4135 (2)0.130 (3)
H1E0.58500.44750.45450.195*
H2E0.54750.38540.39440.195*
H3E0.50970.51110.40550.195*
O1E0.67585 (16)0.6382 (2)0.41991 (11)0.0663 (7)
S1E0.65298 (6)0.52674 (8)0.38849 (5)0.0652 (3)
C2E0.5827 (5)0.5600 (6)0.3216 (2)0.0913 (17)
H1XA0.060 (3)0.669 (3)0.0193 (14)0.054 (10)*
H2A0.006 (3)0.762 (3)0.0449 (16)0.065 (12)*
H3A0.091 (3)0.750 (3)0.0426 (14)0.047 (11)*
H4A0.288 (2)0.516 (2)0.0753 (12)0.025 (8)*
H5A0.253 (2)0.441 (3)0.1149 (13)0.031 (9)*
H6A0.114 (2)0.359 (3)0.1868 (14)0.045 (9)*
H7A0.173 (3)0.431 (3)0.1446 (14)0.040 (10)*
H10A0.008 (2)0.409 (3)0.2689 (13)0.050 (9)*
H11A0.029 (3)0.277 (3)0.3388 (16)0.067 (11)*
H12A0.118 (2)0.114 (3)0.3352 (15)0.053 (10)*
H13A0.177 (2)0.075 (3)0.2551 (14)0.057 (10)*
H14A0.135 (2)0.212 (2)0.1756 (13)0.034 (8)*
H1XB0.488 (2)0.454 (3)0.1282 (14)0.043 (10)*
H2B0.590 (3)0.360 (3)0.1939 (16)0.065 (12)*
H3B0.687 (2)0.353 (3)0.1886 (13)0.035 (9)*
H4B0.790 (3)0.568 (3)0.0570 (13)0.045 (9)*
H5B0.721 (3)0.649 (3)0.0164 (16)0.062 (12)*
H6B0.288 (2)0.762 (3)0.0337 (15)0.049 (10)*
H7B0.264 (2)0.683 (3)0.0076 (13)0.039 (9)*
H10B0.370 (2)0.930 (2)0.0027 (12)0.032 (8)*
H11B0.355 (2)1.087 (3)0.0608 (12)0.030 (8)*
H12B0.422 (2)1.104 (3)0.1356 (15)0.058 (10)*
H13B0.518 (3)0.953 (3)0.1552 (16)0.075 (12)*
H14B0.5265 (19)0.786 (2)0.0945 (11)0.026 (7)*
H4C0.438 (2)0.216 (2)0.3043 (12)0.040 (8)*
H5C0.331 (2)0.158 (3)0.2941 (14)0.061 (10)*
H6C0.378 (3)0.409 (3)0.3030 (15)0.065 (11)*
H7C0.271 (3)0.363 (3)0.2774 (14)0.056 (10)*
H8C0.375 (2)0.319 (2)0.3905 (12)0.032 (8)*
H9C0.273 (3)0.277 (3)0.3621 (14)0.059 (10)*
H10C0.320 (3)0.535 (3)0.3634 (15)0.070 (11)*
H11C0.202 (3)0.473 (3)0.3337 (19)0.091 (13)*
H14C0.211 (3)0.607 (3)0.4663 (18)0.080 (13)*
H15C0.190 (3)0.657 (4)0.4035 (19)0.093 (14)*
H1D0.728 (4)0.062 (5)0.209 (3)0.14 (2)*
H2D0.696 (3)0.042 (4)0.255 (2)0.090 (18)*
H3D0.648 (3)0.144 (4)0.2206 (17)0.072 (13)*
H4D0.659 (2)0.291 (3)0.2969 (14)0.052 (9)*
H5D0.706 (3)0.196 (4)0.3475 (17)0.078 (14)*
H6D0.750 (3)0.313 (3)0.3453 (16)0.063 (12)*
H4E0.605 (5)0.598 (6)0.294 (3)0.17 (3)*
H5E0.534 (4)0.605 (5)0.330 (2)0.11 (2)*
H6E0.557 (4)0.477 (5)0.300 (2)0.14 (2)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.0254 (14)0.0379 (14)0.0429 (15)0.0038 (11)0.0110 (12)0.0122 (12)
C2A0.0298 (17)0.0371 (16)0.0390 (18)0.0000 (13)0.0104 (14)0.0077 (15)
N2A0.0288 (18)0.0572 (18)0.0516 (19)0.0032 (14)0.0151 (15)0.0237 (15)
N3A0.0253 (14)0.0414 (14)0.0410 (14)0.0003 (10)0.0095 (11)0.0088 (12)
C4A0.0273 (17)0.0331 (15)0.0349 (16)0.0003 (12)0.0080 (13)0.0030 (14)
N4A0.0255 (15)0.0426 (16)0.0407 (16)0.0016 (12)0.0110 (13)0.0102 (14)
C4AA0.0280 (17)0.0343 (15)0.0361 (17)0.0013 (12)0.0081 (13)0.0048 (14)
N5A0.0274 (14)0.0350 (13)0.0370 (14)0.0031 (10)0.0104 (11)0.0038 (12)
C6A0.0314 (17)0.0329 (16)0.0374 (17)0.0031 (12)0.0125 (14)0.0036 (13)
C7A0.0276 (16)0.0346 (16)0.0355 (16)0.0023 (12)0.0122 (13)0.0015 (14)
N7A0.0252 (16)0.0493 (17)0.0475 (17)0.0072 (13)0.0116 (13)0.0189 (14)
N8A0.0273 (14)0.0341 (13)0.0415 (14)0.0023 (10)0.0133 (11)0.0073 (12)
C8AA0.0317 (17)0.0318 (15)0.0381 (17)0.0016 (12)0.0113 (14)0.0012 (14)
C9A0.0281 (16)0.0370 (16)0.0376 (17)0.0012 (12)0.0092 (13)0.0058 (14)
C10A0.0408 (19)0.0489 (19)0.0433 (19)0.0153 (15)0.0149 (15)0.0110 (16)
C11A0.046 (2)0.077 (3)0.043 (2)0.0130 (18)0.0188 (17)0.0163 (19)
C12A0.042 (2)0.054 (2)0.050 (2)0.0074 (16)0.0103 (17)0.0205 (19)
C13A0.0356 (19)0.0400 (18)0.057 (2)0.0070 (14)0.0083 (16)0.0083 (17)
C14A0.0295 (17)0.0421 (18)0.0416 (19)0.0042 (13)0.0087 (14)0.0065 (15)
N1B0.0235 (14)0.0355 (14)0.0326 (14)0.0037 (11)0.0090 (11)0.0025 (11)
C2B0.0261 (16)0.0331 (15)0.0328 (16)0.0008 (12)0.0072 (13)0.0009 (14)
N2B0.0265 (16)0.0480 (16)0.0479 (17)0.0034 (13)0.0093 (14)0.0151 (14)
N3B0.0258 (13)0.0319 (13)0.0347 (13)0.0011 (10)0.0089 (11)0.0034 (11)
C4B0.0266 (16)0.0306 (15)0.0322 (16)0.0019 (12)0.0090 (13)0.0038 (13)
N4B0.0252 (15)0.0429 (15)0.0377 (15)0.0016 (11)0.0117 (12)0.0080 (13)
C4AB0.0271 (16)0.0289 (15)0.0273 (15)0.0009 (11)0.0074 (12)0.0001 (13)
N5B0.0260 (13)0.0319 (13)0.0321 (13)0.0003 (10)0.0077 (10)0.0004 (11)
C6B0.0275 (17)0.0314 (15)0.0304 (15)0.0004 (12)0.0069 (12)0.0017 (13)
C7B0.0291 (16)0.0285 (15)0.0300 (15)0.0020 (12)0.0100 (12)0.0032 (13)
N7B0.0246 (15)0.0420 (15)0.0433 (16)0.0016 (12)0.0109 (13)0.0122 (13)
C8AB0.0263 (16)0.0261 (14)0.0287 (15)0.0014 (11)0.0062 (12)0.0010 (12)
N8B0.0239 (13)0.0324 (13)0.0323 (13)0.0004 (10)0.0101 (10)0.0004 (11)
C9B0.0247 (16)0.0327 (15)0.0373 (17)0.0032 (12)0.0059 (13)0.0037 (13)
C10B0.0301 (17)0.0374 (17)0.0431 (18)0.0006 (13)0.0085 (14)0.0039 (15)
C11B0.0265 (17)0.0367 (18)0.060 (2)0.0009 (14)0.0070 (16)0.0033 (17)
C12B0.037 (2)0.051 (2)0.069 (3)0.0009 (16)0.0072 (18)0.028 (2)
C13B0.039 (2)0.066 (2)0.048 (2)0.0023 (17)0.0153 (17)0.0195 (18)
C14B0.0308 (18)0.0426 (19)0.0427 (19)0.0039 (14)0.0081 (15)0.0059 (16)
C1C0.036 (2)0.057 (2)0.046 (2)0.0024 (15)0.0149 (16)0.0047 (17)
O1C0.0320 (12)0.0547 (13)0.0436 (13)0.0024 (10)0.0107 (10)0.0128 (11)
C2C0.046 (2)0.087 (3)0.049 (2)0.0183 (19)0.0108 (18)0.015 (2)
O2C0.0313 (14)0.1009 (19)0.0473 (14)0.0074 (12)0.0055 (11)0.0244 (13)
C3C0.041 (2)0.052 (2)0.053 (2)0.0001 (16)0.0154 (17)0.0155 (17)
O3C0.0363 (13)0.0520 (13)0.0588 (15)0.0051 (10)0.0152 (11)0.0217 (13)
C4C0.049 (2)0.043 (2)0.100 (3)0.0020 (18)0.035 (2)0.016 (2)
O4C0.062 (2)0.149 (3)0.146 (3)0.0565 (19)0.064 (2)0.110 (3)
C5C0.068 (3)0.049 (2)0.120 (4)0.016 (2)0.053 (3)0.035 (3)
C6C0.082 (4)0.092 (3)0.081 (3)0.026 (3)0.023 (3)0.001 (3)
C7C0.085 (4)0.096 (4)0.154 (5)0.048 (3)0.062 (4)0.076 (4)
C8C0.041 (2)0.059 (2)0.070 (3)0.0153 (17)0.026 (2)0.030 (2)
C9C0.0342 (19)0.049 (2)0.060 (2)0.0021 (14)0.0167 (16)0.0164 (18)
C1D0.080 (4)0.047 (3)0.083 (3)0.020 (2)0.019 (3)0.003 (3)
O1D0.0407 (13)0.0449 (12)0.0542 (14)0.0008 (10)0.0111 (11)0.0170 (11)
S1D0.0402 (5)0.0424 (5)0.0488 (5)0.0040 (3)0.0097 (4)0.0105 (4)
C2D0.049 (2)0.067 (3)0.050 (2)0.007 (2)0.011 (2)0.006 (2)
C1E0.164 (6)0.120 (4)0.088 (4)0.071 (4)0.002 (4)0.030 (3)
O1E0.0398 (14)0.0750 (17)0.0842 (18)0.0063 (12)0.0156 (13)0.0426 (15)
S1E0.0404 (5)0.0605 (6)0.0813 (7)0.0143 (4)0.0096 (5)0.0287 (5)
C2E0.096 (4)0.107 (4)0.063 (3)0.029 (4)0.006 (3)0.001 (3)
Geometric parameters (Å, º) top
N1A—C8AA1.362 (4)C9B—C10B1.392 (4)
N1A—C2A1.366 (4)C9B—C14B1.394 (4)
N1A—H1XA0.90 (4)C10B—C11B1.385 (4)
C2A—N2A1.312 (4)C10B—H10B0.97 (3)
C2A—N3A1.351 (4)C11B—C12B1.384 (5)
N2A—H2A0.86 (4)C11B—H11B0.85 (3)
N2A—H3A0.79 (4)C12B—C13B1.380 (5)
N3A—C4A1.335 (4)C12B—H12B0.92 (4)
C4A—N4A1.322 (4)C13B—C14B1.383 (5)
C4A—C4AA1.426 (4)C13B—H13B1.05 (4)
N4A—H4A0.85 (3)C14B—H14B0.89 (3)
N4A—H5A0.81 (3)C1C—O2C1.247 (4)
C4AA—N5A1.356 (4)C1C—O1C1.267 (4)
C4AA—C8AA1.396 (4)C1C—C2C1.519 (5)
N5A—C6A1.312 (4)C2C—C3C1.535 (5)
C6A—C7A1.454 (4)C2C—H2C0.9900
C6A—C9A1.486 (4)C2C—H3C0.9900
C7A—N7A1.331 (4)C3C—C4C1.500 (5)
C7A—N8A1.337 (4)C3C—H4C1.02 (3)
N7A—H6A0.90 (3)C3C—H5C1.06 (4)
N7A—H7A0.78 (4)O3C—C9C1.251 (4)
N8A—C8AA1.349 (4)C4C—C5C1.492 (6)
C9A—C14A1.393 (4)C4C—H6C1.01 (4)
C9A—C10A1.395 (4)C4C—H7C1.03 (4)
C10A—C11A1.392 (5)O4C—C9C1.240 (4)
C10A—H10A0.99 (3)C5C—C6C1.601 (7)
C11A—C12A1.366 (5)C5C—H8C1.01 (3)
C11A—H11A0.93 (4)C5C—H9C1.02 (4)
C12A—C13A1.387 (5)C6C—C7C1.379 (7)
C12A—H12A0.95 (3)C6C—H10C1.08 (4)
C13A—C14A1.391 (4)C6C—H11C1.20 (5)
C13A—H13A1.03 (3)C7C—C8C1.535 (6)
C14A—H14A1.01 (3)C7C—H12C0.9900
N1B—C2B1.354 (4)C7C—H13C0.9900
N1B—C8AB1.370 (4)C8C—C9C1.505 (5)
N1B—H1XB0.82 (4)C8C—H14C0.91 (4)
C2B—N2B1.321 (4)C8C—H15C1.16 (5)
C2B—N3B1.340 (4)C1D—S1D1.794 (4)
N2B—H2B0.90 (4)C1D—H1D1.03 (7)
N2B—H3B0.85 (3)C1D—H2D0.77 (5)
N3B—C4B1.344 (4)C1D—H3D1.00 (4)
C4B—N4B1.329 (4)O1D—S1D1.503 (2)
C4B—C4AB1.434 (4)S1D—C2D1.779 (4)
N4B—H4B0.97 (4)C2D—H4D1.04 (4)
N4B—H5B0.88 (4)C2D—H5D0.91 (4)
C4AB—N5B1.356 (3)C2D—H6D0.94 (4)
C4AB—C8AB1.396 (4)C1E—S1E1.780 (6)
N5B—C6B1.313 (3)C1E—H1E0.9800
C6B—C7B1.449 (4)C1E—H2E0.9800
C6B—C9B1.488 (4)C1E—H3E0.9800
C7B—N7B1.326 (4)O1E—S1E1.489 (2)
C7B—N8B1.350 (3)S1E—C2E1.750 (5)
N7B—H6B0.85 (4)C2E—H4E0.93 (8)
N7B—H7B0.88 (3)C2E—H5E0.96 (5)
C8AB—N8B1.339 (3)C2E—H6E1.10 (6)
C8AA—N1A—C2A120.1 (3)C12B—C11B—C10B120.2 (3)
C8AA—N1A—H1XA124 (2)C12B—C11B—H11B124 (2)
C2A—N1A—H1XA115 (2)C10B—C11B—H11B116 (2)
N2A—C2A—N3A119.5 (3)C13B—C12B—C11B119.8 (3)
N2A—C2A—N1A117.5 (3)C13B—C12B—H12B121 (2)
N3A—C2A—N1A123.0 (3)C11B—C12B—H12B119 (2)
C2A—N2A—H2A122 (3)C12B—C13B—C14B120.4 (3)
C2A—N2A—H3A116 (3)C12B—C13B—H13B119 (2)
H2A—N2A—H3A122 (4)C14B—C13B—H13B120 (2)
C4A—N3A—C2A118.5 (2)C13B—C14B—C9B120.2 (3)
N4A—C4A—N3A118.5 (3)C13B—C14B—H14B122.9 (17)
N4A—C4A—C4AA120.4 (3)C9B—C14B—H14B116.9 (17)
N3A—C4A—C4AA121.1 (3)O2C—C1C—O1C124.6 (3)
C4A—N4A—H4A116.8 (19)O2C—C1C—C2C117.6 (3)
C4A—N4A—H5A116 (2)O1C—C1C—C2C117.7 (3)
H4A—N4A—H5A127 (3)C1C—C2C—C3C114.3 (3)
N5A—C4AA—C8AA120.9 (3)C1C—C2C—H2C108.7
N5A—C4AA—C4A120.5 (2)C3C—C2C—H2C108.7
C8AA—C4AA—C4A118.6 (3)C1C—C2C—H3C108.7
C6A—N5A—C4AA118.6 (2)C3C—C2C—H3C108.7
N5A—C6A—C7A119.9 (3)H2C—C2C—H3C107.6
N5A—C6A—C9A117.1 (2)C4C—C3C—C2C111.7 (3)
C7A—C6A—C9A122.9 (3)C4C—C3C—H4C112.9 (16)
N7A—C7A—N8A117.7 (3)C2C—C3C—H4C103.6 (17)
N7A—C7A—C6A120.5 (3)C4C—C3C—H5C111.1 (19)
N8A—C7A—C6A121.8 (3)C2C—C3C—H5C108.8 (18)
C7A—N7A—H6A120 (2)H4C—C3C—H5C109 (2)
C7A—N7A—H7A122 (2)C5C—C4C—C3C114.6 (3)
H6A—N7A—H7A118 (3)C5C—C4C—H6C104 (2)
C7A—N8A—C8AA116.2 (2)C3C—C4C—H6C113 (2)
N8A—C8AA—N1A118.9 (3)C5C—C4C—H7C102.2 (19)
N8A—C8AA—C4AA122.4 (3)C3C—C4C—H7C112.1 (19)
N1A—C8AA—C4AA118.7 (3)H6C—C4C—H7C110 (3)
C14A—C9A—C10A119.5 (3)C4C—C5C—C6C105.8 (4)
C14A—C9A—C6A118.0 (3)C4C—C5C—H8C112.8 (18)
C10A—C9A—C6A122.5 (3)C6C—C5C—H8C116.8 (17)
C11A—C10A—C9A119.4 (3)C4C—C5C—H9C108.2 (19)
C11A—C10A—H10A116.0 (19)C6C—C5C—H9C110 (2)
C9A—C10A—H10A124.5 (19)H8C—C5C—H9C103 (3)
C12A—C11A—C10A120.8 (3)C7C—C6C—C5C113.4 (5)
C12A—C11A—H11A122 (2)C7C—C6C—H10C105 (2)
C10A—C11A—H11A117 (2)C5C—C6C—H10C111 (2)
C11A—C12A—C13A120.4 (3)C7C—C6C—H11C107 (2)
C11A—C12A—H12A118 (2)C5C—C6C—H11C109 (2)
C13A—C12A—H12A121 (2)H10C—C6C—H11C112 (3)
C12A—C13A—C14A119.6 (3)C6C—C7C—C8C118.3 (5)
C12A—C13A—H13A118.7 (19)C6C—C7C—H12C107.7
C14A—C13A—H13A121.7 (19)C8C—C7C—H12C107.7
C13A—C14A—C9A120.2 (3)C6C—C7C—H13C107.7
C13A—C14A—H14A120.9 (16)C8C—C7C—H13C107.7
C9A—C14A—H14A118.8 (16)H12C—C7C—H13C107.1
C2B—N1B—C8AB119.8 (3)C9C—C8C—C7C115.0 (3)
C2B—N1B—H1XB116 (2)C9C—C8C—H14C111 (3)
C8AB—N1B—H1XB124 (2)C7C—C8C—H14C112 (3)
N2B—C2B—N3B119.0 (3)C9C—C8C—H15C105 (2)
N2B—C2B—N1B116.9 (3)C7C—C8C—H15C113 (2)
N3B—C2B—N1B124.1 (3)H14C—C8C—H15C100 (3)
C2B—N2B—H2B121 (2)O4C—C9C—O3C122.7 (3)
C2B—N2B—H3B122 (2)O4C—C9C—C8C118.3 (3)
H2B—N2B—H3B117 (3)O3C—C9C—C8C118.9 (3)
C2B—N3B—C4B117.9 (2)S1D—C1D—H1D110 (3)
N4B—C4B—N3B117.9 (3)S1D—C1D—H2D114 (4)
N4B—C4B—C4AB121.1 (3)H1D—C1D—H2D98 (5)
N3B—C4B—C4AB121.0 (2)S1D—C1D—H3D110 (2)
C4B—N4B—H4B121.5 (18)H1D—C1D—H3D105 (4)
C4B—N4B—H5B124 (2)H2D—C1D—H3D118 (5)
H4B—N4B—H5B115 (3)O1D—S1D—C2D106.38 (18)
N5B—C4AB—C8AB120.8 (2)O1D—S1D—C1D105.8 (2)
N5B—C4AB—C4B120.9 (2)C2D—S1D—C1D96.6 (2)
C8AB—C4AB—C4B118.2 (2)S1D—C2D—H4D109.8 (18)
C6B—N5B—C4AB118.2 (2)S1D—C2D—H5D108 (3)
N5B—C6B—C7B120.6 (2)H4D—C2D—H5D117 (3)
N5B—C6B—C9B117.3 (2)S1D—C2D—H6D107 (2)
C7B—C6B—C9B122.1 (2)H4D—C2D—H6D106 (3)
N7B—C7B—N8B117.6 (3)H5D—C2D—H6D109 (3)
N7B—C7B—C6B121.6 (3)S1E—C1E—H1E109.5
N8B—C7B—C6B120.8 (2)S1E—C1E—H2E109.5
C7B—N7B—H6B124 (2)H1E—C1E—H2E109.5
C7B—N7B—H7B120 (2)S1E—C1E—H3E109.5
H6B—N7B—H7B116 (3)H1E—C1E—H3E109.5
N8B—C8AB—N1B118.9 (2)H2E—C1E—H3E109.5
N8B—C8AB—C4AB122.5 (2)O1E—S1E—C2E107.4 (3)
N1B—C8AB—C4AB118.6 (2)O1E—S1E—C1E106.9 (2)
C8AB—N8B—C7B116.6 (2)C2E—S1E—C1E94.8 (3)
C10B—C9B—C14B119.1 (3)S1E—C2E—H4E123 (5)
C10B—C9B—C6B121.3 (3)S1E—C2E—H5E104 (3)
C14B—C9B—C6B119.4 (3)H4E—C2E—H5E109 (5)
C11B—C10B—C9B120.2 (3)S1E—C2E—H6E108 (3)
C11B—C10B—H10B121.7 (17)H4E—C2E—H6E101 (5)
C9B—C10B—H10B118.1 (16)H5E—C2E—H6E112 (5)
C8AA—N1A—C2A—N2A179.3 (3)C2B—N3B—C4B—C4AB1.7 (4)
C8AA—N1A—C2A—N3A0.9 (4)N4B—C4B—C4AB—N5B6.7 (4)
N2A—C2A—N3A—C4A179.3 (3)N3B—C4B—C4AB—N5B171.9 (2)
N1A—C2A—N3A—C4A0.9 (4)N4B—C4B—C4AB—C8AB176.9 (2)
C2A—N3A—C4A—N4A179.7 (3)N3B—C4B—C4AB—C8AB4.5 (4)
C2A—N3A—C4A—C4AA0.3 (4)C8AB—C4AB—N5B—C6B2.2 (4)
N4A—C4A—C4AA—N5A3.2 (4)C4B—C4AB—N5B—C6B178.5 (2)
N3A—C4A—C4AA—N5A177.4 (3)C4AB—N5B—C6B—C7B4.3 (4)
N4A—C4A—C4AA—C8AA179.0 (3)C4AB—N5B—C6B—C9B175.0 (2)
N3A—C4A—C4AA—C8AA0.4 (4)N5B—C6B—C7B—N7B171.8 (3)
C8AA—C4AA—N5A—C6A2.6 (4)C9B—C6B—C7B—N7B9.0 (4)
C4A—C4AA—N5A—C6A179.7 (3)N5B—C6B—C7B—N8B7.0 (4)
C4AA—N5A—C6A—C7A1.7 (4)C9B—C6B—C7B—N8B172.2 (2)
C4AA—N5A—C6A—C9A179.0 (2)C2B—N1B—C8AB—N8B178.3 (2)
N5A—C6A—C7A—N7A173.7 (3)C2B—N1B—C8AB—C4AB2.5 (4)
C9A—C6A—C7A—N7A3.4 (4)N5B—C4AB—C8AB—N8B6.8 (4)
N5A—C6A—C7A—N8A5.0 (4)C4B—C4AB—C8AB—N8B176.8 (2)
C9A—C6A—C7A—N8A177.9 (3)N5B—C4AB—C8AB—N1B174.1 (2)
N7A—C7A—N8A—C8AA175.3 (3)C4B—C4AB—C8AB—N1B2.3 (4)
C6A—C7A—N8A—C8AA3.4 (4)N1B—C8AB—N8B—C7B176.8 (2)
C7A—N8A—C8AA—N1A179.4 (2)C4AB—C8AB—N8B—C7B4.0 (4)
C7A—N8A—C8AA—C4AA1.0 (4)N7B—C7B—N8B—C8AB176.3 (2)
C2A—N1A—C8AA—N8A178.7 (3)C6B—C7B—N8B—C8AB2.6 (4)
C2A—N1A—C8AA—C4AA0.2 (4)N5B—C6B—C9B—C10B134.6 (3)
N5A—C4AA—C8AA—N8A4.2 (4)C7B—C6B—C9B—C10B44.7 (4)
C4A—C4AA—C8AA—N8A178.0 (3)N5B—C6B—C9B—C14B40.1 (4)
N5A—C4AA—C8AA—N1A177.4 (2)C7B—C6B—C9B—C14B140.6 (3)
C4A—C4AA—C8AA—N1A0.5 (4)C14B—C9B—C10B—C11B0.5 (4)
N5A—C6A—C9A—C14A43.4 (4)C6B—C9B—C10B—C11B175.2 (3)
C7A—C6A—C9A—C14A133.8 (3)C9B—C10B—C11B—C12B0.1 (5)
N5A—C6A—C9A—C10A135.1 (3)C10B—C11B—C12B—C13B0.1 (5)
C7A—C6A—C9A—C10A47.8 (4)C11B—C12B—C13B—C14B0.6 (5)
C14A—C9A—C10A—C11A1.4 (5)C12B—C13B—C14B—C9B1.3 (5)
C6A—C9A—C10A—C11A179.8 (3)C10B—C9B—C14B—C13B1.2 (5)
C9A—C10A—C11A—C12A0.3 (5)C6B—C9B—C14B—C13B176.0 (3)
C10A—C11A—C12A—C13A0.4 (6)O2C—C1C—C2C—C3C43.7 (5)
C11A—C12A—C13A—C14A0.0 (5)O1C—C1C—C2C—C3C139.6 (3)
C12A—C13A—C14A—C9A1.0 (5)C1C—C2C—C3C—C4C66.8 (4)
C10A—C9A—C14A—C13A1.7 (5)C2C—C3C—C4C—C5C168.9 (4)
C6A—C9A—C14A—C13A179.7 (3)C3C—C4C—C5C—C6C175.7 (4)
C8AB—N1B—C2B—N2B174.2 (2)C4C—C5C—C6C—C7C177.7 (4)
C8AB—N1B—C2B—N3B5.8 (4)C5C—C6C—C7C—C8C163.3 (4)
N2B—C2B—N3B—C4B176.5 (2)C6C—C7C—C8C—C9C73.9 (6)
N1B—C2B—N3B—C4B3.6 (4)C7C—C8C—C9C—O4C34.6 (6)
C2B—N3B—C4B—N4B179.7 (2)C7C—C8C—C9C—O3C147.4 (4)
Triamterenium nicotinate, Triamterene and DMSO solvate (1f_DMSO) top
Crystal data top
C12H12N7+·C12H11N7·C6H4NO2·2(C2H6OS)F(000) = 1648
Mr = 785.92Dx = 1.391 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.7107 Å
a = 14.8461 (2) ÅCell parameters from 12872 reflections
b = 12.3081 (3) Åθ = 1.0–27.5°
c = 21.2850 (5) ŵ = 0.20 mm1
β = 105.176 (1)°T = 180 K
V = 3753.71 (14) Å3Needle, colourless
Z = 40.35 × 0.07 × 0.05 mm
Data collection top
Nonius Kappa CCD
diffractometer
8467 independent reflections
Radiation source: fine-focus sealed tube4823 reflections with I > 2σ(I)
None monochromatorRint = 0.048
Thin slice ω and φ scansθmax = 27.5°, θmin = 3.6°
Absorption correction: multi-scan
multi-scan from symmetry-related measurements Sortav (Blessing 1995)
h = 1818
Tmin = 0.878, Tmax = 0.998k = 1515
23512 measured reflectionsl = 2327
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: difference Fourier map
wR(F2) = 0.089All H-atom parameters refined
S = 0.90 w = 1/[σ2(Fo2) + (0.0421P)2]
where P = (Fo2 + 2Fc2)/3
8467 reflections(Δ/σ)max = 0.001
652 parametersΔρmax = 0.25 e Å3
0 restraintsΔρmin = 0.38 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
N1A0.50349 (9)0.97687 (12)0.09678 (7)0.0247 (3)
C2A0.41465 (11)1.01475 (15)0.11949 (8)0.0251 (4)
N2A0.40045 (12)1.09028 (14)0.16462 (8)0.0338 (4)
N3A0.34284 (9)0.97948 (12)0.09733 (7)0.0258 (3)
C4A0.35902 (11)0.90257 (15)0.05166 (8)0.0264 (4)
N4A0.29044 (11)0.86944 (15)0.02724 (9)0.0349 (4)
C4AA0.44969 (10)0.85334 (14)0.02924 (8)0.0235 (4)
N5A0.46282 (9)0.76746 (12)0.01158 (7)0.0265 (3)
C6A0.54657 (11)0.72222 (15)0.02947 (8)0.0254 (4)
C7A0.62309 (10)0.77077 (15)0.00823 (8)0.0253 (4)
N7A0.71046 (10)0.73422 (15)0.02993 (8)0.0336 (4)
N8A0.60930 (9)0.85484 (12)0.03334 (7)0.0259 (3)
C8AA0.52169 (11)0.89398 (14)0.05286 (8)0.0234 (4)
C9A0.55417 (11)0.62417 (15)0.07036 (8)0.0269 (4)
C10A0.60248 (11)0.53138 (15)0.06050 (9)0.0308 (4)
C11A0.60030 (13)0.43801 (18)0.09633 (10)0.0378 (5)
C12A0.54991 (13)0.4353 (2)0.14244 (11)0.0464 (6)
C13A0.50157 (14)0.52630 (18)0.15238 (11)0.0461 (6)
C14A0.50341 (12)0.61933 (18)0.11719 (10)0.0365 (5)
N1B0.54573 (8)0.67340 (11)0.48290 (7)0.0248 (3)
C2B0.47207 (11)0.71323 (14)0.50096 (8)0.0243 (4)
N2B0.48694 (12)0.79830 (13)0.54194 (8)0.0308 (4)
N3B0.38149 (9)0.67861 (11)0.48130 (7)0.0259 (3)
C4B0.36431 (10)0.59581 (14)0.43962 (8)0.0239 (4)
N4B0.27735 (10)0.55648 (15)0.42071 (8)0.0322 (4)
C4AB0.43605 (10)0.54897 (14)0.41463 (8)0.0221 (4)
N5B0.41666 (8)0.46844 (12)0.36999 (7)0.0245 (3)
C6B0.48556 (10)0.42646 (14)0.34926 (8)0.0237 (4)
C7B0.57981 (11)0.46831 (15)0.37552 (8)0.0262 (4)
N7B0.65092 (11)0.42923 (15)0.35457 (9)0.0366 (4)
N8B0.59877 (8)0.54823 (12)0.41902 (7)0.0251 (3)
C8AB0.52656 (11)0.59078 (14)0.43988 (8)0.0230 (4)
C9B0.46308 (11)0.34259 (14)0.29729 (8)0.0246 (4)
C10B0.38469 (12)0.35676 (17)0.24519 (9)0.0298 (4)
C11B0.36085 (13)0.28155 (17)0.19574 (10)0.0358 (5)
C12B0.41309 (13)0.18934 (18)0.19744 (10)0.0373 (5)
C13B0.49067 (13)0.17225 (17)0.24905 (10)0.0339 (5)
C14B0.51598 (12)0.24872 (15)0.29855 (9)0.0283 (4)
C1C0.11345 (12)0.34819 (16)0.31962 (10)0.0310 (4)
N1C0.32325 (9)0.16232 (13)0.35956 (7)0.0345 (4)
O1C0.13421 (8)0.40303 (11)0.37145 (6)0.0385 (3)
C2C0.18117 (11)0.26128 (15)0.31212 (8)0.0274 (4)
O2C0.04021 (8)0.35890 (12)0.27467 (6)0.0430 (4)
C3C0.16455 (12)0.19592 (16)0.25733 (9)0.0325 (5)
C4C0.22744 (13)0.11582 (17)0.25385 (11)0.0362 (5)
C5C0.30433 (13)0.10133 (17)0.30589 (10)0.0364 (5)
C6C0.26183 (12)0.24197 (16)0.36115 (10)0.0315 (5)
C1D0.3279 (2)0.0730 (4)0.50649 (14)0.0749 (10)
O1D0.34563 (8)0.07683 (10)0.59712 (6)0.0361 (3)
S1D0.35120 (3)0.04385 (4)0.59078 (2)0.03692 (14)
C2D0.47179 (15)0.0791 (2)0.61244 (14)0.0482 (6)
C1E0.75030 (17)0.0960 (2)0.27410 (12)0.0424 (5)
O1E0.72885 (8)0.30753 (10)0.26855 (6)0.0417 (4)
S1E0.72396 (3)0.21220 (4)0.22365 (2)0.03268 (13)
C2E0.82962 (18)0.2158 (2)0.19862 (14)0.0479 (6)
H1XA0.5484 (14)1.0172 (17)0.1121 (10)0.058 (6)*
H2A0.4464 (13)1.1079 (15)0.1839 (9)0.044 (6)*
H3A0.3482 (12)1.1185 (14)0.1798 (8)0.025 (5)*
H4A0.2324 (14)0.9000 (15)0.0404 (9)0.041 (6)*
H5A0.3032 (12)0.8271 (16)0.0044 (10)0.036 (6)*
H6A0.7228 (11)0.6777 (15)0.0569 (9)0.029 (5)*
H7A0.7548 (13)0.7650 (17)0.0161 (9)0.047 (6)*
H10A0.6336 (11)0.5303 (13)0.0244 (8)0.029 (5)*
H11A0.6325 (12)0.3762 (16)0.0889 (9)0.040 (5)*
H12A0.5477 (13)0.3710 (18)0.1645 (10)0.051 (6)*
H13A0.4674 (15)0.5227 (17)0.1852 (11)0.064 (7)*
H14A0.4692 (11)0.6839 (14)0.1224 (8)0.026 (5)*
H2B0.5464 (14)0.8130 (16)0.5671 (10)0.048 (6)*
H3B0.4411 (13)0.8219 (15)0.5593 (9)0.041 (6)*
H4B0.2336 (13)0.5860 (15)0.4394 (9)0.041 (5)*
H5B0.2676 (11)0.4969 (15)0.3970 (9)0.028 (5)*
H6B0.6428 (11)0.3876 (15)0.3250 (9)0.024 (6)*
H7B0.7043 (13)0.4580 (15)0.3703 (9)0.031 (5)*
H10B0.3500 (11)0.4188 (15)0.2447 (8)0.028 (5)*
H11B0.3083 (12)0.2926 (15)0.1619 (9)0.040 (5)*
H12B0.3969 (11)0.1331 (16)0.1650 (9)0.035 (5)*
H13B0.5266 (11)0.1058 (15)0.2529 (8)0.033 (5)*
H14B0.5694 (11)0.2343 (14)0.3361 (8)0.029 (5)*
H3C0.1096 (12)0.2099 (14)0.2235 (8)0.028 (5)*
H4C0.2189 (11)0.0739 (15)0.2199 (9)0.034 (5)*
H5C0.3460 (12)0.0455 (15)0.3048 (8)0.033 (5)*
H6C0.2814 (10)0.2873 (14)0.4004 (8)0.029 (5)*
H1D0.2649 (19)0.061 (2)0.4886 (12)0.081 (8)*
H2D0.3672 (19)0.022 (2)0.4877 (13)0.092 (10)*
H3D0.3356 (17)0.149 (2)0.5031 (12)0.083 (10)*
H4D0.4949 (16)0.062 (2)0.6572 (14)0.086 (9)*
H5D0.4759 (15)0.155 (2)0.6015 (11)0.069 (8)*
H6D0.5042 (15)0.0331 (19)0.5894 (11)0.061 (7)*
H1E0.7036 (15)0.0889 (18)0.2950 (11)0.068 (7)*
H2E0.8067 (14)0.1109 (15)0.3049 (10)0.044 (6)*
H3E0.7542 (13)0.0323 (18)0.2503 (10)0.052 (7)*
H4E0.8795 (15)0.2191 (17)0.2379 (11)0.058 (7)*
H5E0.8252 (15)0.280 (2)0.1736 (11)0.068 (8)*
H6E0.8314 (13)0.1531 (19)0.1727 (10)0.055 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.0200 (8)0.0273 (9)0.0273 (9)0.0012 (6)0.0070 (6)0.0043 (7)
C2A0.0239 (9)0.0260 (11)0.0247 (10)0.0002 (8)0.0047 (7)0.0022 (9)
N2A0.0209 (9)0.0397 (11)0.0407 (11)0.0047 (8)0.0081 (8)0.0137 (9)
N3A0.0224 (7)0.0284 (9)0.0275 (9)0.0013 (6)0.0079 (6)0.0014 (7)
C4A0.0233 (9)0.0302 (11)0.0265 (11)0.0002 (8)0.0079 (7)0.0040 (9)
N4A0.0236 (9)0.0452 (12)0.0377 (11)0.0084 (8)0.0111 (8)0.0168 (9)
C4AA0.0217 (9)0.0246 (11)0.0246 (10)0.0003 (7)0.0070 (7)0.0013 (9)
N5A0.0241 (8)0.0290 (10)0.0267 (9)0.0011 (6)0.0068 (6)0.0006 (7)
C6A0.0234 (9)0.0281 (11)0.0247 (10)0.0017 (8)0.0061 (7)0.0018 (9)
C7A0.0210 (9)0.0291 (11)0.0265 (10)0.0022 (8)0.0072 (7)0.0014 (9)
N7A0.0209 (9)0.0362 (11)0.0447 (11)0.0040 (7)0.0102 (7)0.0170 (9)
N8A0.0201 (7)0.0296 (9)0.0281 (9)0.0039 (6)0.0067 (6)0.0019 (8)
C8AA0.0239 (9)0.0234 (11)0.0231 (10)0.0005 (7)0.0065 (7)0.0029 (9)
C9A0.0206 (8)0.0276 (11)0.0315 (11)0.0003 (7)0.0052 (7)0.0017 (9)
C10A0.0233 (9)0.0322 (12)0.0349 (12)0.0003 (8)0.0043 (8)0.0009 (10)
C11A0.0297 (10)0.0290 (13)0.0495 (14)0.0021 (9)0.0009 (9)0.0016 (11)
C12A0.0379 (12)0.0391 (15)0.0608 (16)0.0053 (10)0.0104 (10)0.0198 (13)
C13A0.0427 (12)0.0459 (15)0.0559 (15)0.0028 (11)0.0241 (11)0.0166 (12)
C14A0.0326 (11)0.0362 (13)0.0438 (13)0.0063 (9)0.0156 (9)0.0092 (11)
N1B0.0219 (7)0.0249 (9)0.0282 (9)0.0002 (6)0.0077 (6)0.0027 (7)
C2B0.0243 (9)0.0251 (11)0.0238 (10)0.0007 (8)0.0067 (7)0.0024 (9)
N2B0.0239 (9)0.0338 (10)0.0357 (10)0.0006 (7)0.0094 (8)0.0117 (8)
N3B0.0214 (7)0.0266 (9)0.0308 (9)0.0029 (6)0.0088 (6)0.0037 (7)
C4B0.0188 (9)0.0258 (11)0.0274 (10)0.0005 (7)0.0068 (7)0.0019 (9)
N4B0.0224 (9)0.0358 (11)0.0408 (10)0.0038 (7)0.0127 (7)0.0140 (9)
C4AB0.0219 (9)0.0236 (10)0.0209 (10)0.0009 (7)0.0058 (7)0.0014 (8)
N5B0.0215 (7)0.0260 (9)0.0269 (9)0.0014 (6)0.0080 (6)0.0006 (7)
C6B0.0233 (9)0.0239 (11)0.0240 (10)0.0008 (7)0.0061 (7)0.0020 (8)
C7B0.0208 (9)0.0301 (11)0.0290 (11)0.0016 (8)0.0093 (7)0.0001 (9)
N7B0.0215 (9)0.0452 (12)0.0455 (12)0.0071 (8)0.0133 (8)0.0230 (10)
N8B0.0215 (7)0.0260 (9)0.0291 (9)0.0020 (6)0.0088 (6)0.0041 (7)
C8AB0.0216 (9)0.0246 (11)0.0242 (10)0.0009 (7)0.0084 (7)0.0042 (9)
C9B0.0232 (9)0.0250 (11)0.0276 (10)0.0047 (8)0.0102 (8)0.0017 (9)
C10B0.0277 (10)0.0308 (12)0.0319 (12)0.0005 (9)0.0094 (8)0.0019 (10)
C11B0.0285 (10)0.0465 (14)0.0313 (12)0.0058 (10)0.0062 (9)0.0046 (11)
C12B0.0357 (11)0.0410 (14)0.0391 (13)0.0097 (10)0.0166 (10)0.0153 (11)
C13B0.0307 (10)0.0293 (12)0.0462 (13)0.0015 (9)0.0183 (9)0.0066 (10)
C14B0.0245 (9)0.0286 (11)0.0336 (12)0.0023 (8)0.0109 (8)0.0022 (9)
C1C0.0248 (10)0.0338 (12)0.0363 (12)0.0036 (8)0.0113 (9)0.0006 (10)
N1C0.0309 (8)0.0371 (10)0.0357 (10)0.0005 (7)0.0092 (7)0.0031 (8)
O1C0.0266 (7)0.0426 (9)0.0454 (9)0.0015 (6)0.0077 (6)0.0177 (7)
C2C0.0242 (9)0.0305 (11)0.0298 (11)0.0043 (8)0.0114 (8)0.0014 (9)
O2C0.0316 (7)0.0605 (10)0.0352 (8)0.0108 (6)0.0055 (6)0.0030 (7)
C3C0.0255 (10)0.0411 (13)0.0305 (12)0.0039 (9)0.0066 (9)0.0018 (10)
C4C0.0400 (12)0.0368 (13)0.0347 (13)0.0075 (10)0.0148 (10)0.0110 (11)
C5C0.0331 (11)0.0315 (13)0.0477 (14)0.0017 (9)0.0160 (10)0.0013 (11)
C6C0.0292 (10)0.0358 (13)0.0311 (12)0.0041 (9)0.0109 (8)0.0042 (10)
C1D0.0506 (17)0.105 (3)0.0602 (19)0.0246 (18)0.0018 (14)0.0338 (19)
O1D0.0345 (7)0.0304 (8)0.0452 (8)0.0037 (6)0.0136 (6)0.0015 (7)
S1D0.0364 (3)0.0339 (3)0.0439 (3)0.0003 (2)0.0165 (2)0.0015 (3)
C2D0.0450 (13)0.0483 (18)0.0496 (17)0.0121 (12)0.0096 (12)0.0013 (14)
C1E0.0400 (13)0.0455 (16)0.0427 (14)0.0034 (11)0.0122 (12)0.0006 (12)
O1E0.0313 (7)0.0418 (9)0.0536 (9)0.0039 (6)0.0138 (6)0.0203 (7)
S1E0.0321 (3)0.0331 (3)0.0321 (3)0.0001 (2)0.0071 (2)0.0054 (2)
C2E0.0579 (15)0.0424 (16)0.0543 (17)0.0016 (12)0.0342 (14)0.0041 (15)
Geometric parameters (Å, º) top
N1A—C8AA1.362 (2)C6B—C9B1.486 (2)
N1A—C2A1.363 (2)C7B—N8B1.329 (2)
N1A—H1XA0.95 (2)C7B—N7B1.338 (2)
C2A—N2A1.314 (2)N7B—H6B0.796 (18)
C2A—N3A1.346 (2)N7B—H7B0.853 (18)
N2A—H2A0.91 (2)N8B—C8AB1.367 (2)
N2A—H3A0.834 (17)C9B—C10B1.392 (2)
N3A—C4A1.333 (2)C9B—C14B1.393 (2)
C4A—N4A1.323 (2)C10B—C11B1.377 (3)
C4A—C4AA1.439 (2)C10B—H10B0.919 (18)
N4A—H4A0.91 (2)C11B—C12B1.370 (3)
N4A—H5A0.83 (2)C11B—H11B0.923 (18)
C4AA—N5A1.350 (2)C12B—C13B1.384 (3)
C4AA—C8AA1.388 (2)C12B—H12B0.963 (19)
N5A—C6A1.324 (2)C13B—C14B1.389 (3)
C6A—C7A1.456 (2)C13B—H13B0.968 (18)
C6A—C9A1.475 (2)C14B—H14B0.983 (17)
C7A—N7A1.336 (2)C1C—O2C1.253 (2)
C7A—N8A1.342 (2)C1C—O1C1.261 (2)
N7A—H6A0.890 (19)C1C—C2C1.505 (2)
N7A—H7A0.88 (2)N1C—C5C1.334 (2)
N8A—C8AA1.347 (2)N1C—C6C1.345 (2)
C9A—C10A1.394 (2)C2C—C3C1.385 (2)
C9A—C14A1.399 (2)C2C—C6C1.388 (2)
C10A—C11A1.384 (3)C3C—C4C1.373 (3)
C10A—H10A0.996 (17)C3C—H3C0.952 (17)
C11A—C12A1.381 (3)C4C—C5C1.378 (3)
C11A—H11A0.934 (19)C4C—H4C0.870 (18)
C12A—C13A1.376 (3)C5C—H5C0.929 (18)
C12A—H12A0.93 (2)C6C—H6C0.983 (17)
C13A—C14A1.372 (3)C1D—S1D1.773 (3)
C13A—H13A0.96 (2)C1D—H1D0.92 (3)
C14A—H14A0.965 (17)C1D—H2D1.01 (3)
N1B—C2B1.343 (2)C1D—H3D0.95 (3)
N1B—C8AB1.348 (2)O1D—S1D1.4957 (13)
C2B—N2B1.344 (2)S1D—C2D1.782 (2)
C2B—N3B1.368 (2)C2D—H4D0.95 (3)
N2B—H2B0.92 (2)C2D—H5D0.97 (3)
N2B—H3B0.903 (19)C2D—H6D0.96 (2)
N3B—C4B1.331 (2)C1E—S1E1.769 (2)
C4B—N4B1.338 (2)C1E—H1E0.92 (2)
C4B—C4AB1.430 (2)C1E—H2E0.94 (2)
N4B—H4B0.921 (19)C1E—H3E0.94 (2)
N4B—H5B0.881 (19)O1E—S1E1.5029 (13)
C4AB—N5B1.351 (2)S1E—C2E1.784 (2)
C4AB—C8AB1.408 (2)C2E—H4E0.96 (2)
N5B—C6B1.321 (2)C2E—H5E0.94 (3)
C6B—C7B1.458 (2)C2E—H6E0.95 (2)
C8AA—N1A—C2A119.95 (14)C7B—N7B—H6B121.8 (12)
C8AA—N1A—H1XA126.3 (12)C7B—N7B—H7B116.9 (12)
C2A—N1A—H1XA113.5 (12)H6B—N7B—H7B120.7 (17)
N2A—C2A—N3A119.63 (15)C7B—N8B—C8AB117.94 (13)
N2A—C2A—N1A117.17 (15)N1B—C8AB—N8B117.74 (14)
N3A—C2A—N1A123.19 (16)N1B—C8AB—C4AB123.09 (14)
C2A—N2A—H2A120.2 (12)N8B—C8AB—C4AB119.15 (16)
C2A—N2A—H3A122.3 (12)C10B—C9B—C14B117.94 (17)
H2A—N2A—H3A117.2 (17)C10B—C9B—C6B118.94 (16)
C4A—N3A—C2A118.47 (13)C14B—C9B—C6B123.11 (15)
N4A—C4A—N3A119.68 (16)C11B—C10B—C9B121.24 (19)
N4A—C4A—C4AA119.30 (17)C11B—C10B—H10B121.2 (10)
N3A—C4A—C4AA121.01 (14)C9B—C10B—H10B117.5 (10)
C4A—N4A—H4A120.9 (12)C12B—C11B—C10B120.44 (19)
C4A—N4A—H5A118.3 (12)C12B—C11B—H11B119.9 (12)
H4A—N4A—H5A120.1 (17)C10B—C11B—H11B119.6 (12)
N5A—C4AA—C8AA121.35 (14)C11B—C12B—C13B119.6 (2)
N5A—C4AA—C4A120.54 (14)C11B—C12B—H12B122.9 (11)
C8AA—C4AA—C4A118.06 (16)C13B—C12B—H12B117.4 (11)
C6A—N5A—C4AA118.74 (14)C12B—C13B—C14B120.18 (19)
N5A—C6A—C7A119.23 (16)C12B—C13B—H13B121.4 (10)
N5A—C6A—C9A115.77 (14)C14B—C13B—H13B118.3 (10)
C7A—C6A—C9A125.01 (14)C13B—C14B—C9B120.53 (18)
N7A—C7A—N8A117.03 (15)C13B—C14B—H14B119.6 (10)
N7A—C7A—C6A121.34 (17)C9B—C14B—H14B119.8 (10)
N8A—C7A—C6A121.63 (14)O2C—C1C—O1C125.19 (17)
C7A—N7A—H6A120.3 (10)O2C—C1C—C2C117.64 (17)
C7A—N7A—H7A119.1 (13)O1C—C1C—C2C117.15 (16)
H6A—N7A—H7A120.6 (17)C5C—N1C—C6C116.08 (17)
C7A—N8A—C8AA116.58 (13)C3C—C2C—C6C117.54 (17)
N8A—C8AA—N1A118.79 (14)C3C—C2C—C1C121.71 (16)
N8A—C8AA—C4AA122.18 (16)C6C—C2C—C1C120.73 (17)
N1A—C8AA—C4AA119.03 (15)C4C—C3C—C2C119.26 (18)
C10A—C9A—C14A117.82 (17)C4C—C3C—H3C123.4 (10)
C10A—C9A—C6A122.99 (15)C2C—C3C—H3C117.4 (10)
C14A—C9A—C6A118.89 (16)C3C—C4C—C5C118.8 (2)
C11A—C10A—C9A120.68 (18)C3C—C4C—H4C121.2 (12)
C11A—C10A—H10A119.8 (10)C5C—C4C—H4C120.0 (12)
C9A—C10A—H10A119.3 (10)N1C—C5C—C4C124.0 (2)
C12A—C11A—C10A120.4 (2)N1C—C5C—H5C116.5 (11)
C12A—C11A—H11A119.8 (11)C4C—C5C—H5C119.5 (11)
C10A—C11A—H11A119.8 (11)N1C—C6C—C2C124.26 (18)
C13A—C12A—C11A119.4 (2)N1C—C6C—H6C112.6 (9)
C13A—C12A—H12A122.0 (12)C2C—C6C—H6C123.1 (9)
C11A—C12A—H12A118.6 (12)S1D—C1D—H1D107.0 (15)
C14A—C13A—C12A120.6 (2)S1D—C1D—H2D107.1 (16)
C14A—C13A—H13A121.5 (13)H1D—C1D—H2D111 (2)
C12A—C13A—H13A117.9 (13)S1D—C1D—H3D106.4 (16)
C13A—C14A—C9A121.05 (19)H1D—C1D—H3D105 (2)
C13A—C14A—H14A122.6 (10)H2D—C1D—H3D119 (2)
C9A—C14A—H14A116.3 (10)O1D—S1D—C1D106.96 (16)
C2B—N1B—C8AB115.26 (13)O1D—S1D—C2D107.10 (11)
N1B—C2B—N2B117.55 (15)C1D—S1D—C2D97.41 (14)
N1B—C2B—N3B127.43 (16)S1D—C2D—H4D106.3 (14)
N2B—C2B—N3B115.01 (15)S1D—C2D—H5D107.2 (13)
C2B—N2B—H2B119.9 (12)H4D—C2D—H5D115 (2)
C2B—N2B—H3B120.2 (12)S1D—C2D—H6D109.2 (13)
H2B—N2B—H3B114.1 (17)H4D—C2D—H6D107 (2)
C4B—N3B—C2B116.36 (13)H5D—C2D—H6D112.0 (19)
N3B—C4B—N4B118.61 (15)S1E—C1E—H1E107.2 (14)
N3B—C4B—C4AB121.66 (14)S1E—C1E—H2E106.4 (12)
N4B—C4B—C4AB119.73 (17)H1E—C1E—H2E109.2 (18)
C4B—N4B—H4B117.5 (11)S1E—C1E—H3E112.4 (13)
C4B—N4B—H5B118.3 (11)H1E—C1E—H3E109.9 (19)
H4B—N4B—H5B123.2 (16)H2E—C1E—H3E111.7 (17)
N5B—C4AB—C8AB122.90 (14)O1E—S1E—C1E106.18 (11)
N5B—C4AB—C4B121.00 (14)O1E—S1E—C2E105.70 (11)
C8AB—C4AB—C4B116.10 (15)C1E—S1E—C2E97.43 (13)
C6B—N5B—C4AB118.75 (13)S1E—C2E—H4E106.2 (12)
N5B—C6B—C7B118.90 (15)S1E—C2E—H5E104.6 (13)
N5B—C6B—C9B118.54 (14)H4E—C2E—H5E112.4 (19)
C7B—C6B—C9B122.47 (14)S1E—C2E—H6E108.2 (12)
N8B—C7B—N7B117.15 (15)H4E—C2E—H6E114.0 (18)
N8B—C7B—C6B122.36 (14)H5E—C2E—H6E110.9 (18)
N7B—C7B—C6B120.45 (17)
C8AA—N1A—C2A—N2A176.04 (16)N3B—C4B—C4AB—N5B176.78 (15)
C8AA—N1A—C2A—N3A4.8 (2)N4B—C4B—C4AB—N5B2.9 (2)
N2A—C2A—N3A—C4A179.82 (16)N3B—C4B—C4AB—C8AB4.0 (2)
N1A—C2A—N3A—C4A1.1 (2)N4B—C4B—C4AB—C8AB176.39 (16)
C2A—N3A—C4A—N4A177.40 (16)C8AB—C4AB—N5B—C6B0.4 (2)
C2A—N3A—C4A—C4AA3.8 (2)C4B—C4AB—N5B—C6B178.79 (15)
N4A—C4A—C4AA—N5A6.2 (3)C4AB—N5B—C6B—C7B0.2 (2)
N3A—C4A—C4AA—N5A172.61 (15)C4AB—N5B—C6B—C9B176.38 (14)
N4A—C4A—C4AA—C8AA176.31 (16)N5B—C6B—C7B—N8B0.9 (2)
N3A—C4A—C4AA—C8AA4.9 (2)C9B—C6B—C7B—N8B175.60 (16)
C8AA—C4AA—N5A—C6A0.5 (2)N5B—C6B—C7B—N7B178.56 (17)
C4A—C4AA—N5A—C6A177.86 (15)C9B—C6B—C7B—N7B2.1 (3)
C4AA—N5A—C6A—C7A4.1 (2)N7B—C7B—N8B—C8AB178.58 (16)
C4AA—N5A—C6A—C9A175.86 (15)C6B—C7B—N8B—C8AB0.8 (2)
N5A—C6A—C7A—N7A173.67 (16)C2B—N1B—C8AB—N8B178.99 (14)
C9A—C6A—C7A—N7A6.3 (3)C2B—N1B—C8AB—C4AB0.7 (2)
N5A—C6A—C7A—N8A5.6 (2)C7B—N8B—C8AB—N1B178.58 (15)
C9A—C6A—C7A—N8A174.43 (16)C7B—N8B—C8AB—C4AB0.2 (2)
N7A—C7A—N8A—C8AA177.36 (15)N5B—C4AB—C8AB—N1B177.86 (15)
C6A—C7A—N8A—C8AA1.9 (2)C4B—C4AB—C8AB—N1B2.9 (2)
C7A—N8A—C8AA—N1A177.78 (15)N5B—C4AB—C8AB—N8B0.4 (2)
C7A—N8A—C8AA—C4AA2.8 (2)C4B—C4AB—C8AB—N8B178.77 (15)
C2A—N1A—C8AA—N8A177.11 (15)N5B—C6B—C9B—C10B41.8 (2)
C2A—N1A—C8AA—C4AA3.5 (2)C7B—C6B—C9B—C10B134.70 (17)
N5A—C4AA—C8AA—N8A4.3 (3)N5B—C6B—C9B—C14B137.09 (17)
C4A—C4AA—C8AA—N8A178.27 (15)C7B—C6B—C9B—C14B46.4 (2)
N5A—C4AA—C8AA—N1A176.34 (15)C14B—C9B—C10B—C11B1.1 (3)
C4A—C4AA—C8AA—N1A1.1 (2)C6B—C9B—C10B—C11B179.92 (15)
N5A—C6A—C9A—C10A136.32 (17)C9B—C10B—C11B—C12B1.4 (3)
C7A—C6A—C9A—C10A43.7 (3)C10B—C11B—C12B—C13B0.4 (3)
N5A—C6A—C9A—C14A37.3 (2)C11B—C12B—C13B—C14B0.6 (3)
C7A—C6A—C9A—C14A142.73 (17)C12B—C13B—C14B—C9B0.8 (3)
C14A—C9A—C10A—C11A0.3 (3)C10B—C9B—C14B—C13B0.1 (2)
C6A—C9A—C10A—C11A173.98 (16)C6B—C9B—C14B—C13B178.95 (15)
C9A—C10A—C11A—C12A0.1 (3)O2C—C1C—C2C—C3C0.9 (3)
C10A—C11A—C12A—C13A0.2 (3)O1C—C1C—C2C—C3C179.43 (16)
C11A—C12A—C13A—C14A0.3 (3)O2C—C1C—C2C—C6C177.38 (16)
C12A—C13A—C14A—C9A0.1 (3)O1C—C1C—C2C—C6C1.2 (2)
C10A—C9A—C14A—C13A0.2 (3)C6C—C2C—C3C—C4C0.1 (3)
C6A—C9A—C14A—C13A174.13 (18)C1C—C2C—C3C—C4C178.17 (17)
C8AB—N1B—C2B—N2B177.61 (15)C2C—C3C—C4C—C5C1.5 (3)
C8AB—N1B—C2B—N3B0.9 (2)C6C—N1C—C5C—C4C0.0 (3)
N1B—C2B—N3B—C4B0.2 (2)C3C—C4C—C5C—N1C1.7 (3)
N2B—C2B—N3B—C4B178.69 (15)C5C—N1C—C6C—C2C1.8 (3)
C2B—N3B—C4B—N4B177.67 (15)C3C—C2C—C6C—N1C1.9 (3)
C2B—N3B—C4B—C4AB2.7 (2)C1C—C2C—C6C—N1C176.45 (16)
Triamterene and Ibuprofen, DMSO solvate (1g_DMSO) top
Crystal data top
C12H12N7+·C12H11N7·C13H17O2·C2H6OSZ = 2
Mr = 790.96F(000) = 836
Triclinic, P1Dx = 1.294 Mg m3
a = 11.2398 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 13.2439 (3) ÅCell parameters from 53045 reflections
c = 15.4624 (4) Åθ = 1.0–27.5°
α = 113.595 (2)°µ = 0.14 mm1
β = 103.527 (3)°T = 180 K
γ = 91.977 (2)°Block, colourless
V = 2029.46 (10) Å30.30 × 0.14 × 0.10 mm
Data collection top
Nonius Kappa CCD
diffractometer
9204 independent reflections
Radiation source: fine-focus sealed tube6189 reflections with I > 2σ(I)
None monochromatorRint = 0.041
Thin slice ω and φ scansθmax = 27.5°, θmin = 2.4°
Absorption correction: multi-scan
multi-scan from symmetry-related measurements Sortav (Blessing 1995)
h = 1414
Tmin = 0.880, Tmax = 0.991k = 1716
30734 measured reflectionsl = 1920
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.074Hydrogen site location: mixed
wR(F2) = 0.215H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0959P)2 + 1.9185P]
where P = (Fo2 + 2Fc2)/3
9204 reflections(Δ/σ)max < 0.001
626 parametersΔρmax = 1.23 e Å3
0 restraintsΔρmin = 0.42 e Å3
Special details top

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
N1A0.1580 (2)0.58904 (19)0.05356 (16)0.0349 (5)
C2A0.2523 (2)0.5292 (2)0.06433 (18)0.0336 (5)
N2A0.2557 (2)0.4802 (2)0.12371 (17)0.0386 (5)
N3A0.3413 (2)0.51942 (18)0.01767 (15)0.0343 (5)
C4A0.3353 (2)0.5687 (2)0.04378 (18)0.0327 (5)
N4A0.4246 (2)0.5613 (2)0.08795 (18)0.0401 (5)
C4AA0.2359 (2)0.6294 (2)0.06092 (18)0.0327 (5)
N5A0.2315 (2)0.67980 (18)0.12262 (15)0.0354 (5)
C6A0.1412 (3)0.7376 (2)0.13250 (19)0.0362 (6)
C7A0.0465 (3)0.7437 (2)0.0816 (2)0.0393 (6)
N7A0.0486 (3)0.7979 (2)0.0944 (2)0.0508 (7)
N8A0.0521 (2)0.69449 (19)0.01987 (16)0.0381 (5)
C8AA0.1472 (2)0.6391 (2)0.01040 (18)0.0336 (5)
C9A0.1409 (3)0.7963 (2)0.1967 (2)0.0395 (6)
C10A0.1512 (3)0.7379 (3)0.2910 (2)0.0480 (7)
C11A0.1598 (4)0.7914 (3)0.3503 (3)0.0587 (9)
C12A0.1607 (4)0.9050 (3)0.3145 (3)0.0630 (10)
C13A0.1512 (4)0.9647 (3)0.2207 (3)0.0623 (9)
C14A0.1393 (3)0.9106 (3)0.1624 (2)0.0499 (7)
N1B0.9051 (2)0.48861 (18)0.75212 (15)0.0356 (5)
C2B0.8819 (2)0.5190 (2)0.67762 (19)0.0352 (6)
N2B0.7901 (3)0.5808 (2)0.6725 (2)0.0483 (7)
N3B0.9400 (2)0.49352 (19)0.60561 (15)0.0366 (5)
C4B1.0342 (2)0.4349 (2)0.61084 (18)0.0345 (6)
N4B1.0957 (3)0.4103 (2)0.54329 (19)0.0473 (6)
C4AB1.0680 (2)0.3989 (2)0.68796 (18)0.0317 (5)
N5B1.16367 (19)0.34036 (18)0.69376 (15)0.0333 (5)
C6B1.1881 (2)0.3055 (2)0.76368 (18)0.0325 (5)
C7B1.1102 (2)0.3273 (2)0.83063 (18)0.0322 (5)
N7B1.1227 (2)0.2821 (2)0.89521 (17)0.0385 (5)
N8B1.0186 (2)0.38842 (17)0.82688 (15)0.0331 (5)
C8AB0.9974 (2)0.4264 (2)0.75588 (17)0.0310 (5)
C9B1.2899 (2)0.2372 (2)0.7657 (2)0.0365 (6)
C10B1.3742 (3)0.2482 (3)0.8513 (2)0.0436 (7)
C11B1.4680 (3)0.1816 (3)0.8485 (3)0.0530 (8)
C12B1.4773 (3)0.1036 (3)0.7601 (3)0.0569 (9)
C13B1.3954 (3)0.0930 (3)0.6746 (3)0.0550 (8)
C14B1.3019 (3)0.1583 (3)0.6761 (2)0.0442 (7)
C1C0.3513 (3)0.2246 (3)0.0917 (3)0.0511 (8)
O1C0.2561 (2)0.1976 (2)0.02344 (17)0.0569 (6)
C2C0.4081 (4)0.1283 (4)0.1095 (4)0.0796 (13)
H1C0.38930.06510.04290.095*
O2C0.4016 (2)0.3234 (2)0.1472 (2)0.0660 (7)
C3C0.5376 (4)0.1430 (5)0.1459 (6)0.130 (3)
H2C0.56380.20820.20910.195*
H3C0.57650.15420.09930.195*
H4C0.56250.07680.15460.195*
C4C0.3337 (4)0.0902 (3)0.1650 (3)0.0596 (9)
C5C0.3407 (5)0.1532 (3)0.2619 (4)0.0902 (14)
H5C0.39180.22350.29580.108*
C6C0.2734 (5)0.1155 (3)0.3119 (3)0.0887 (15)
H6C0.28000.16090.37890.106*
C7C0.2004 (4)0.0173 (3)0.2675 (3)0.0694 (11)
C8C0.1885 (4)0.0428 (4)0.1704 (3)0.0732 (11)
H8C0.13420.11130.13620.088*
C9C0.2535 (4)0.0068 (4)0.1203 (3)0.0678 (10)
H9C0.24210.05100.05240.081*
C10C0.1327 (5)0.0260 (5)0.3231 (4)0.0959 (16)
H11C0.10850.03840.37270.115*
H10C0.05560.07410.27620.115*
C11C0.1976 (5)0.0868 (4)0.3712 (4)0.0923 (15)
H12C0.26680.02960.42270.111*
C12C0.1212 (6)0.1144 (4)0.4320 (4)0.1084 (19)
H13C0.08750.04810.46860.163*
H14C0.17440.13840.47800.163*
H15C0.05310.17440.38800.163*
C13C0.2597 (5)0.1758 (4)0.3250 (4)0.0985 (16)
H16C0.19890.24130.27940.148*
H17C0.31440.19370.37480.148*
H18C0.30880.15410.28890.148*
S1D0.55329 (9)0.57198 (8)0.43456 (7)0.0535 (3)0.91
O1D0.6714 (7)0.6402 (3)0.5071 (4)0.0537 (10)0.91
C1D0.5264 (5)0.6190 (5)0.3393 (4)0.0719 (14)0.91
H1D0.50670.69520.36460.108*0.91
H2D0.45700.57000.28470.108*0.91
H3D0.60070.61760.31620.108*0.91
C2D0.5957 (6)0.4417 (4)0.3651 (5)0.1042 (18)0.91
H4D0.61740.40120.40620.156*0.91
H5D0.66690.45440.34250.156*0.91
H6D0.52600.39770.30830.156*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'0.43160.59220.49350.115*0.09
H2D'0.35970.65430.43160.115*0.09
H3D'0.42540.72270.54620.115*0.09
C2D'0.483 (6)0.633 (6)0.357 (5)0.076 (3)*0.09
H4D'0.39830.62000.36060.115*0.09
H5D'0.51030.56230.32290.115*0.09
H6D'0.48580.68030.32210.115*0.09
H1XA0.103 (3)0.595 (3)0.085 (2)0.046 (9)*
H2A0.198 (3)0.486 (2)0.152 (2)0.036 (7)*
H3A0.307 (3)0.429 (3)0.122 (2)0.056 (10)*
H4A0.489 (3)0.529 (3)0.074 (2)0.050 (9)*
H5A0.432 (3)0.604 (3)0.121 (2)0.047 (8)*
H6A0.051 (3)0.831 (3)0.139 (3)0.061 (10)*
H7A0.112 (3)0.797 (3)0.066 (3)0.055 (9)*
H10A0.151 (3)0.665 (3)0.312 (2)0.045 (8)*
H11A0.170 (3)0.751 (3)0.418 (3)0.064 (10)*
H12A0.161 (3)0.939 (3)0.357 (3)0.067 (10)*
H13A0.147 (3)1.044 (3)0.193 (3)0.066 (10)*
H14A0.136 (3)0.955 (3)0.098 (3)0.055 (9)*
H2B0.753 (3)0.596 (3)0.713 (3)0.048 (9)*
H3B0.771 (3)0.603 (3)0.625 (2)0.046 (8)*
H4B1.079 (3)0.436 (3)0.499 (3)0.055 (9)*
H5B1.160 (3)0.374 (3)0.546 (2)0.045 (8)*
H6B1.182 (3)0.250 (2)0.909 (2)0.035 (8)*
H7B1.072 (3)0.297 (3)0.932 (2)0.043 (8)*
H10B1.369 (2)0.300 (2)0.910 (2)0.032 (7)*
H11B1.521 (3)0.194 (3)0.912 (3)0.056 (9)*
H12B1.538 (3)0.057 (3)0.760 (3)0.065 (10)*
H13B1.399 (4)0.044 (3)0.616 (3)0.071 (12)*
H14B1.245 (3)0.154 (2)0.613 (2)0.043 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.0382 (12)0.0453 (13)0.0343 (12)0.0144 (10)0.0166 (10)0.0254 (10)
C2A0.0378 (14)0.0375 (13)0.0323 (13)0.0088 (11)0.0127 (11)0.0194 (11)
N2A0.0418 (13)0.0517 (14)0.0422 (13)0.0193 (11)0.0223 (11)0.0324 (11)
N3A0.0359 (11)0.0396 (11)0.0371 (12)0.0094 (9)0.0143 (9)0.0232 (10)
C4A0.0367 (13)0.0342 (13)0.0323 (13)0.0042 (10)0.0101 (10)0.0186 (11)
N4A0.0404 (13)0.0518 (14)0.0485 (14)0.0164 (11)0.0215 (11)0.0355 (12)
C4AA0.0369 (13)0.0361 (13)0.0318 (13)0.0055 (11)0.0100 (10)0.0205 (11)
N5A0.0425 (12)0.0362 (11)0.0343 (11)0.0066 (9)0.0119 (9)0.0208 (10)
C6A0.0416 (14)0.0384 (13)0.0338 (13)0.0064 (11)0.0098 (11)0.0207 (11)
C7A0.0461 (15)0.0432 (15)0.0359 (14)0.0121 (12)0.0118 (12)0.0230 (12)
N7A0.0527 (16)0.0719 (18)0.0561 (16)0.0310 (14)0.0253 (13)0.0474 (15)
N8A0.0416 (12)0.0470 (13)0.0387 (12)0.0147 (10)0.0161 (10)0.0276 (11)
C8AA0.0397 (14)0.0373 (13)0.0291 (12)0.0079 (11)0.0109 (10)0.0182 (11)
C9A0.0439 (15)0.0423 (14)0.0421 (15)0.0075 (12)0.0109 (12)0.0278 (13)
C10A0.063 (2)0.0433 (17)0.0456 (17)0.0044 (14)0.0171 (14)0.0259 (14)
C11A0.076 (2)0.067 (2)0.0473 (19)0.0060 (18)0.0208 (17)0.0357 (17)
C12A0.079 (2)0.068 (2)0.060 (2)0.0029 (18)0.0133 (18)0.049 (2)
C13A0.083 (3)0.0458 (18)0.066 (2)0.0089 (17)0.0101 (19)0.0369 (17)
C14A0.067 (2)0.0464 (17)0.0437 (17)0.0135 (15)0.0113 (15)0.0274 (15)
N1B0.0428 (12)0.0429 (12)0.0340 (11)0.0140 (10)0.0161 (10)0.0253 (10)
C2B0.0394 (14)0.0406 (14)0.0356 (13)0.0114 (11)0.0121 (11)0.0245 (12)
N2B0.0581 (16)0.0696 (17)0.0448 (14)0.0339 (14)0.0265 (13)0.0427 (14)
N3B0.0422 (12)0.0474 (13)0.0332 (11)0.0151 (10)0.0140 (9)0.0272 (10)
C4B0.0397 (14)0.0408 (14)0.0323 (13)0.0092 (11)0.0125 (11)0.0229 (11)
N4B0.0533 (15)0.0710 (17)0.0462 (14)0.0318 (14)0.0271 (12)0.0439 (14)
C4AB0.0363 (13)0.0350 (12)0.0308 (12)0.0076 (10)0.0104 (10)0.0198 (11)
N5B0.0366 (11)0.0384 (11)0.0331 (11)0.0078 (9)0.0109 (9)0.0223 (10)
C6B0.0372 (13)0.0340 (13)0.0321 (13)0.0066 (10)0.0099 (10)0.0191 (11)
C7B0.0371 (13)0.0346 (13)0.0294 (12)0.0046 (10)0.0085 (10)0.0183 (11)
N7B0.0431 (13)0.0492 (14)0.0394 (13)0.0176 (11)0.0161 (11)0.0313 (11)
N8B0.0390 (12)0.0378 (11)0.0318 (11)0.0103 (9)0.0122 (9)0.0222 (9)
C8AB0.0368 (13)0.0320 (12)0.0295 (12)0.0051 (10)0.0096 (10)0.0177 (10)
C9B0.0375 (14)0.0416 (14)0.0436 (15)0.0091 (11)0.0137 (11)0.0293 (12)
C10B0.0426 (16)0.0487 (16)0.0498 (18)0.0117 (13)0.0118 (13)0.0308 (15)
C11B0.0448 (17)0.064 (2)0.067 (2)0.0155 (15)0.0116 (16)0.0463 (18)
C12B0.0543 (19)0.062 (2)0.084 (3)0.0295 (16)0.0315 (18)0.051 (2)
C13B0.063 (2)0.060 (2)0.063 (2)0.0280 (17)0.0329 (18)0.0368 (18)
C14B0.0492 (17)0.0516 (17)0.0471 (17)0.0200 (14)0.0215 (14)0.0303 (14)
C1C0.0481 (18)0.064 (2)0.080 (2)0.0255 (16)0.0347 (17)0.0582 (19)
O1C0.0631 (14)0.0714 (15)0.0619 (14)0.0239 (12)0.0240 (12)0.0486 (13)
C2C0.075 (3)0.102 (3)0.132 (4)0.053 (2)0.054 (3)0.102 (3)
O2C0.0498 (13)0.0761 (17)0.0969 (19)0.0133 (12)0.0128 (13)0.0648 (16)
C3C0.070 (3)0.141 (5)0.248 (8)0.032 (3)0.036 (4)0.154 (6)
C4C0.078 (2)0.064 (2)0.072 (2)0.0378 (19)0.0321 (19)0.055 (2)
C5C0.139 (4)0.044 (2)0.094 (3)0.001 (2)0.033 (3)0.036 (2)
C6C0.155 (5)0.055 (2)0.065 (3)0.017 (3)0.047 (3)0.025 (2)
C7C0.094 (3)0.067 (2)0.081 (3)0.033 (2)0.043 (2)0.053 (2)
C8C0.071 (2)0.098 (3)0.066 (2)0.002 (2)0.0064 (19)0.059 (2)
C9C0.068 (2)0.092 (3)0.058 (2)0.004 (2)0.0090 (17)0.052 (2)
C10C0.108 (4)0.126 (4)0.115 (4)0.044 (3)0.063 (3)0.092 (3)
C11C0.149 (5)0.071 (3)0.099 (3)0.021 (3)0.069 (3)0.057 (3)
C12C0.175 (6)0.089 (3)0.090 (3)0.002 (3)0.071 (4)0.049 (3)
C13C0.083 (3)0.106 (4)0.151 (5)0.018 (3)0.041 (3)0.093 (4)
S1D0.0589 (6)0.0615 (5)0.0522 (5)0.0103 (4)0.0166 (4)0.0348 (4)
O1D0.0607 (17)0.060 (3)0.0397 (18)0.024 (2)0.0108 (14)0.0200 (19)
C1D0.069 (3)0.092 (3)0.064 (3)0.006 (3)0.006 (2)0.049 (3)
C2D0.104 (4)0.068 (3)0.114 (4)0.015 (3)0.010 (3)0.021 (3)
Geometric parameters (Å, º) top
N1A—C2A1.364 (3)C11B—C12B1.374 (5)
N1A—C8AA1.381 (3)C11B—H11B0.96 (4)
N1A—H1XA0.86 (3)C12B—C13B1.374 (5)
C2A—N2A1.314 (3)C12B—H12B0.93 (4)
C2A—N3A1.346 (3)C13B—C14B1.382 (4)
N2A—H2A0.86 (3)C13B—H13B0.89 (4)
N2A—H3A0.90 (4)C14B—H14B1.01 (3)
N3A—C4A1.343 (3)C1C—O1C1.237 (4)
C4A—N4A1.326 (3)C1C—O2C1.261 (4)
C4A—C4AA1.434 (4)C1C—C2C1.538 (4)
N4A—H4A0.88 (3)C2C—C3C1.407 (6)
N4A—H5A0.92 (3)C2C—C4C1.531 (5)
C4AA—N5A1.360 (3)C2C—H1C1.0000
C4AA—C8AA1.383 (4)C3C—H2C0.9800
N5A—C6A1.308 (3)C3C—H3C0.9800
C6A—C7A1.452 (4)C3C—H4C0.9800
C6A—C9A1.485 (3)C4C—C9C1.363 (5)
C7A—N7A1.328 (4)C4C—C5C1.375 (6)
C7A—N8A1.346 (3)C5C—C6C1.405 (6)
N7A—H6A0.95 (4)C5C—H5C0.9500
N7A—H7A0.92 (4)C6C—C7C1.335 (6)
N8A—C8AA1.331 (3)C6C—H6C0.9500
C9A—C10A1.386 (4)C7C—C8C1.360 (6)
C9A—C14A1.392 (4)C7C—C10C1.522 (5)
C10A—C11A1.382 (4)C8C—C9C1.377 (5)
C10A—H10A0.88 (3)C8C—H8C0.9500
C11A—C12A1.378 (5)C9C—H9C0.9500
C11A—H11A1.00 (4)C10C—C11C1.414 (6)
C12A—C13A1.378 (5)C10C—H11C0.9900
C12A—H12A0.94 (4)C10C—H10C0.9900
C13A—C14A1.383 (4)C11C—C13C1.415 (7)
C13A—H13A0.98 (4)C11C—C12C1.545 (6)
C14A—H14A0.94 (3)C11C—H12C1.0000
N1B—C2B1.340 (3)C12C—H13C0.9800
N1B—C8AB1.352 (3)C12C—H14C0.9800
C2B—N2B1.346 (4)C12C—H15C0.9800
C2B—N3B1.355 (3)C13C—H16C0.9800
N2B—H2B0.80 (3)C13C—H17C0.9800
N2B—H3B0.89 (3)C13C—H18C0.9800
N3B—C4B1.341 (3)S1D—O1D1.498 (7)
C4B—N4B1.325 (3)S1D—C2D1.781 (5)
C4B—C4AB1.432 (3)S1D—C1D1.786 (5)
N4B—H4B0.87 (4)C1D—H1D0.9800
N4B—H5B0.89 (3)C1D—H2D0.9800
C4AB—N5B1.354 (3)C1D—H3D0.9800
C4AB—C8AB1.403 (3)C2D—H4D0.9800
N5B—C6B1.314 (3)C2D—H5D0.9800
C6B—C7B1.457 (3)C2D—H6D0.9800
C6B—C9B1.485 (3)S1D'—C2D'1.49 (7)
C7B—N8B1.336 (3)S1D'—O1D'1.69 (9)
C7B—N7B1.339 (3)S1D'—C1D'1.74 (5)
N7B—H6B0.83 (3)C1D'—H1D'0.9800
N7B—H7B0.88 (3)C1D'—H2D'0.9800
N8B—C8AB1.358 (3)C1D'—H3D'0.9800
C9B—C10B1.385 (4)C2D'—H4D'0.9800
C9B—C14B1.403 (4)C2D'—H5D'0.9800
C10B—C11B1.395 (4)C2D'—H6D'0.9800
C10B—H10B0.91 (3)
C2A—N1A—C8AA120.5 (2)C12B—C13B—C14B120.9 (3)
C2A—N1A—H1XA121 (2)C12B—C13B—H13B123 (3)
C8AA—N1A—H1XA118 (2)C14B—C13B—H13B116 (3)
N2A—C2A—N3A119.3 (2)C13B—C14B—C9B120.1 (3)
N2A—C2A—N1A117.9 (2)C13B—C14B—H14B121.2 (17)
N3A—C2A—N1A122.8 (2)C9B—C14B—H14B118.6 (17)
C2A—N2A—H2A119.0 (19)O1C—C1C—O2C125.0 (3)
C2A—N2A—H3A118 (2)O1C—C1C—C2C115.8 (3)
H2A—N2A—H3A121 (3)O2C—C1C—C2C119.2 (3)
C4A—N3A—C2A118.5 (2)C3C—C2C—C4C115.8 (4)
N4A—C4A—N3A118.4 (2)C3C—C2C—C1C117.0 (4)
N4A—C4A—C4AA120.2 (2)C4C—C2C—C1C108.3 (3)
N3A—C4A—C4AA121.3 (2)C3C—C2C—H1C104.8
C4A—N4A—H4A121 (2)C4C—C2C—H1C104.8
C4A—N4A—H5A121 (2)C1C—C2C—H1C104.8
H4A—N4A—H5A117 (3)C2C—C3C—H2C109.5
N5A—C4AA—C8AA120.7 (2)C2C—C3C—H3C109.5
N5A—C4AA—C4A120.8 (2)H2C—C3C—H3C109.5
C8AA—C4AA—C4A118.5 (2)C2C—C3C—H4C109.5
C6A—N5A—C4AA118.1 (2)H2C—C3C—H4C109.5
N5A—C6A—C7A120.5 (2)H3C—C3C—H4C109.5
N5A—C6A—C9A117.4 (2)C9C—C4C—C5C115.9 (3)
C7A—C6A—C9A122.1 (2)C9C—C4C—C2C122.0 (4)
N7A—C7A—N8A117.8 (2)C5C—C4C—C2C122.1 (4)
N7A—C7A—C6A121.1 (2)C4C—C5C—C6C121.1 (4)
N8A—C7A—C6A121.0 (2)C4C—C5C—H5C119.5
C7A—N7A—H6A116 (2)C6C—C5C—H5C119.5
C7A—N7A—H7A121 (2)C7C—C6C—C5C121.7 (4)
H6A—N7A—H7A123 (3)C7C—C6C—H6C119.2
C8AA—N8A—C7A116.1 (2)C5C—C6C—H6C119.2
N8A—C8AA—N1A118.1 (2)C6C—C7C—C8C117.4 (4)
N8A—C8AA—C4AA123.5 (2)C6C—C7C—C10C121.6 (4)
N1A—C8AA—C4AA118.4 (2)C8C—C7C—C10C121.0 (4)
C10A—C9A—C14A118.7 (3)C7C—C8C—C9C121.5 (4)
C10A—C9A—C6A119.5 (2)C7C—C8C—H8C119.2
C14A—C9A—C6A121.6 (3)C9C—C8C—H8C119.2
C11A—C10A—C9A121.0 (3)C4C—C9C—C8C122.3 (4)
C11A—C10A—H10A121 (2)C4C—C9C—H9C118.9
C9A—C10A—H10A118 (2)C8C—C9C—H9C118.9
C12A—C11A—C10A119.5 (3)C11C—C10C—C7C116.9 (4)
C12A—C11A—H11A119 (2)C11C—C10C—H11C108.1
C10A—C11A—H11A122 (2)C7C—C10C—H11C108.1
C13A—C12A—C11A120.3 (3)C11C—C10C—H10C108.1
C13A—C12A—H12A121 (2)C7C—C10C—H10C108.1
C11A—C12A—H12A118 (2)H11C—C10C—H10C107.3
C12A—C13A—C14A120.1 (3)C10C—C11C—C13C123.3 (4)
C12A—C13A—H13A123 (2)C10C—C11C—C12C110.2 (5)
C14A—C13A—H13A117 (2)C13C—C11C—C12C112.1 (4)
C13A—C14A—C9A120.3 (3)C10C—C11C—H12C102.8
C13A—C14A—H14A117 (2)C13C—C11C—H12C102.8
C9A—C14A—H14A122 (2)C12C—C11C—H12C102.8
C2B—N1B—C8AB116.1 (2)C11C—C12C—H13C109.5
N1B—C2B—N2B117.0 (2)C11C—C12C—H14C109.5
N1B—C2B—N3B127.2 (2)H13C—C12C—H14C109.5
N2B—C2B—N3B115.9 (2)C11C—C12C—H15C109.5
C2B—N2B—H2B118 (2)H13C—C12C—H15C109.5
C2B—N2B—H3B120 (2)H14C—C12C—H15C109.5
H2B—N2B—H3B122 (3)C11C—C13C—H16C109.5
C4B—N3B—C2B116.9 (2)C11C—C13C—H17C109.5
N4B—C4B—N3B119.0 (2)H16C—C13C—H17C109.5
N4B—C4B—C4AB120.3 (2)C11C—C13C—H18C109.5
N3B—C4B—C4AB120.7 (2)H16C—C13C—H18C109.5
C4B—N4B—H4B121 (2)H17C—C13C—H18C109.5
C4B—N4B—H5B121 (2)O1D—S1D—C2D105.1 (3)
H4B—N4B—H5B117 (3)O1D—S1D—C1D105.6 (3)
N5B—C4AB—C8AB122.2 (2)C2D—S1D—C1D95.9 (3)
N5B—C4AB—C4B120.7 (2)S1D—C1D—H1D109.5
C8AB—C4AB—C4B117.1 (2)S1D—C1D—H2D109.5
C6B—N5B—C4AB118.5 (2)H1D—C1D—H2D109.5
N5B—C6B—C7B119.7 (2)S1D—C1D—H3D109.5
N5B—C6B—C9B117.4 (2)H1D—C1D—H3D109.5
C7B—C6B—C9B122.7 (2)H2D—C1D—H3D109.5
N8B—C7B—N7B116.8 (2)S1D—C2D—H4D109.5
N8B—C7B—C6B121.6 (2)S1D—C2D—H5D109.5
N7B—C7B—C6B121.5 (2)H4D—C2D—H5D109.5
C7B—N7B—H6B124 (2)S1D—C2D—H6D109.5
C7B—N7B—H7B117 (2)H4D—C2D—H6D109.5
H6B—N7B—H7B118 (3)H5D—C2D—H6D109.5
C7B—N8B—C8AB117.6 (2)C2D'—S1D'—O1D'117 (4)
N1B—C8AB—N8B117.7 (2)C2D'—S1D'—C1D'80 (3)
N1B—C8AB—C4AB122.0 (2)O1D'—S1D'—C1D'105 (4)
N8B—C8AB—C4AB120.3 (2)S1D'—C1D'—H1D'109.5
C10B—C9B—C14B118.4 (3)S1D'—C1D'—H2D'109.5
C10B—C9B—C6B123.5 (3)H1D'—C1D'—H2D'109.5
C14B—C9B—C6B118.1 (2)S1D'—C1D'—H3D'109.5
C9B—C10B—C11B120.8 (3)H1D'—C1D'—H3D'109.5
C9B—C10B—H10B119.8 (17)H2D'—C1D'—H3D'109.5
C11B—C10B—H10B119.5 (18)S1D'—C2D'—H4D'109.5
C12B—C11B—C10B120.0 (3)S1D'—C2D'—H5D'109.5
C12B—C11B—H11B125 (2)H4D'—C2D'—H5D'109.5
C10B—C11B—H11B115 (2)S1D'—C2D'—H6D'109.5
C13B—C12B—C11B119.8 (3)H4D'—C2D'—H6D'109.5
C13B—C12B—H12B121 (2)H5D'—C2D'—H6D'109.5
C11B—C12B—H12B119 (2)
C8AA—N1A—C2A—N2A177.8 (2)C4B—C4AB—N5B—C6B177.4 (2)
C8AA—N1A—C2A—N3A2.9 (4)C4AB—N5B—C6B—C7B1.9 (4)
N2A—C2A—N3A—C4A179.1 (2)C4AB—N5B—C6B—C9B177.3 (2)
N1A—C2A—N3A—C4A1.6 (4)N5B—C6B—C7B—N8B4.4 (4)
C2A—N3A—C4A—N4A178.4 (2)C9B—C6B—C7B—N8B179.6 (2)
C2A—N3A—C4A—C4AA0.8 (4)N5B—C6B—C7B—N7B172.0 (2)
N4A—C4A—C4AA—N5A0.2 (4)C9B—C6B—C7B—N7B3.2 (4)
N3A—C4A—C4AA—N5A179.4 (2)N7B—C7B—N8B—C8AB174.1 (2)
N4A—C4A—C4AA—C8AA177.4 (3)C6B—C7B—N8B—C8AB2.4 (4)
N3A—C4A—C4AA—C8AA1.8 (4)C2B—N1B—C8AB—N8B176.1 (2)
C8AA—C4AA—N5A—C6A0.1 (4)C2B—N1B—C8AB—C4AB2.4 (4)
C4A—C4AA—N5A—C6A177.4 (2)C7B—N8B—C8AB—N1B179.8 (2)
C4AA—N5A—C6A—C7A2.3 (4)C7B—N8B—C8AB—C4AB1.7 (4)
C4AA—N5A—C6A—C9A177.3 (2)N5B—C4AB—C8AB—N1B177.3 (2)
N5A—C6A—C7A—N7A176.9 (3)C4B—C4AB—C8AB—N1B3.0 (4)
C9A—C6A—C7A—N7A3.5 (4)N5B—C4AB—C8AB—N8B4.2 (4)
N5A—C6A—C7A—N8A3.0 (4)C4B—C4AB—C8AB—N8B175.4 (2)
C9A—C6A—C7A—N8A176.6 (3)N5B—C6B—C9B—C10B139.9 (3)
N7A—C7A—N8A—C8AA178.7 (3)C7B—C6B—C9B—C10B44.8 (4)
C6A—C7A—N8A—C8AA1.2 (4)N5B—C6B—C9B—C14B39.4 (4)
C7A—N8A—C8AA—N1A178.8 (2)C7B—C6B—C9B—C14B135.9 (3)
C7A—N8A—C8AA—C4AA1.0 (4)C14B—C9B—C10B—C11B0.7 (4)
C2A—N1A—C8AA—N8A178.5 (2)C6B—C9B—C10B—C11B180.0 (3)
C2A—N1A—C8AA—C4AA1.7 (4)C9B—C10B—C11B—C12B0.2 (5)
N5A—C4AA—C8AA—N8A1.7 (4)C10B—C11B—C12B—C13B1.2 (5)
C4A—C4AA—C8AA—N8A179.2 (2)C11B—C12B—C13B—C14B1.3 (5)
N5A—C4AA—C8AA—N1A178.1 (2)C12B—C13B—C14B—C9B0.3 (5)
C4A—C4AA—C8AA—N1A0.5 (4)C10B—C9B—C14B—C13B0.6 (4)
N5A—C6A—C9A—C10A51.6 (4)C6B—C9B—C14B—C13B180.0 (3)
C7A—C6A—C9A—C10A128.8 (3)O1C—C1C—C2C—C3C148.3 (5)
N5A—C6A—C9A—C14A123.8 (3)O2C—C1C—C2C—C3C33.1 (6)
C7A—C6A—C9A—C14A55.8 (4)O1C—C1C—C2C—C4C78.6 (4)
C14A—C9A—C10A—C11A0.1 (5)O2C—C1C—C2C—C4C99.9 (4)
C6A—C9A—C10A—C11A175.5 (3)C3C—C2C—C4C—C9C120.4 (5)
C9A—C10A—C11A—C12A1.3 (5)C1C—C2C—C4C—C9C106.0 (4)
C10A—C11A—C12A—C13A1.0 (6)C3C—C2C—C4C—C5C61.7 (6)
C11A—C12A—C13A—C14A0.7 (6)C1C—C2C—C4C—C5C72.0 (5)
C12A—C13A—C14A—C9A2.1 (6)C9C—C4C—C5C—C6C3.2 (6)
C10A—C9A—C14A—C13A1.8 (5)C2C—C4C—C5C—C6C178.7 (4)
C6A—C9A—C14A—C13A173.7 (3)C4C—C5C—C6C—C7C0.1 (8)
C8AB—N1B—C2B—N2B179.9 (3)C5C—C6C—C7C—C8C3.2 (7)
C8AB—N1B—C2B—N3B0.6 (4)C5C—C6C—C7C—C10C176.9 (4)
N1B—C2B—N3B—C4B2.7 (4)C6C—C7C—C8C—C9C2.9 (6)
N2B—C2B—N3B—C4B178.0 (3)C10C—C7C—C8C—C9C177.1 (4)
C2B—N3B—C4B—N4B178.4 (3)C5C—C4C—C9C—C8C3.5 (6)
C2B—N3B—C4B—C4AB1.8 (4)C2C—C4C—C9C—C8C178.4 (3)
N4B—C4B—C4AB—N5B0.7 (4)C7C—C8C—C9C—C4C0.5 (6)
N3B—C4B—C4AB—N5B179.5 (2)C6C—C7C—C10C—C11C87.1 (6)
N4B—C4B—C4AB—C8AB179.0 (3)C8C—C7C—C10C—C11C93.0 (6)
N3B—C4B—C4AB—C8AB0.8 (4)C7C—C10C—C11C—C13C49.4 (8)
C8AB—C4AB—N5B—C6B2.2 (4)C7C—C10C—C11C—C12C174.4 (5)
 

Acknowledgements

DSH would like to thank the Department of Chemistry at the University of Cambridge for granting the visiting status that allowed him to develop many of the ideas proposed in this paper. The authors would like to acknowledge Dr John E. Davies for collecting and processing the single-crystal X-ray data used in this study. Professor Joel Bernstein is also thanked for helpful correspondence concerning motif analysis and graph sets and Dr Neil Feeder for helpful discussions on motif and synthon searches of the CSD.

Funding information

AR would like to thank the Islamic Development Bank, in collaboration with the Saudi Arabia and Cambridge Commonwealth Trust, for the award of a studentship to study at the University of Cambridge. AD would like to thank the Pfizer Institute for Pharmaceutical Materials Science for funding.

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IUCrJ
Volume 5| Part 3| May 2018| Pages 309-324
ISSN: 2052-2525