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ISSN: 2052-5206

Heterocyclic 1,3-diazepine-based thio­nes and selones as versatile halogen-bond acceptors

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aDepartment of Chemistry, Clemson University, 219 Hunter Laboratories, Clemson, SC 29634, USA, bDepartment of Chemistry, University of North Carolina at Charlotte, 9201 University City Blvd, Charlotte, NC 28223, USA, cDepartment of Chemistry and Biochemistry, University of Massachusetts Dartmouth, North Dartmouth, MA 02747, USA, and dJoint School of Nanoscience and Nanoengineering, 2907 E. Gate City Blvd, Greensboro, NC 27401, USA
*Correspondence e-mail: billp@clemson.edu

Edited by C. M. Reddy, IISER Kolkata, India (Received 25 January 2022; accepted 15 August 2022; online 31 August 2022)

Utilizing the N-heterocyclic chalcogenones hexa­hydro-1,3-bis­(2,4,6-tri­methyl­phenyl)-2H-1,3-diazepine-2-thione (SDiazMesS) and hexa­hydro-1,3-bis­(2,4,6-tri­methyl­phenyl)-2H-1,3-diazepine-2-selone (SDiazMesSe) as halogen-bond acceptors, a total of 24 new cocrystals were prepared. The solid-state structures of the parent molecules were also determined, along with those of their aceto­nitrile solvates. Through the reaction of the chalcogen atom with molecular diiodine, a variety of S—I—I and Se—I—I fragments were formed, spanning a wide range of I—I bond orders. With acetone as a reaction solvent, molecular diiodine causes the oxidative addition of acetone to the chalcogen atom, resulting in new C—S, C—Se and C—C covalent bonds under mild conditions. The common halogen-bond donors, iodo­penta­fluoro­benzene, 1,2-, 1,3- and 1,4-di­iodo­tetra­fluoro­benzene, 1,3,5-tri­fluoro­tri­iodo­benzene and tetra­iodo­ethyl­ene resulted in halogen-bond-driven cocrystal formation. In most cases, the analogous SDiazMesS and SDiazMesSe cocrystals are isomorphic.

1. Introduction

Halogen bonding has long been known, and formally defined by the International Union of Pure and Applied Chemistry (IUPAC) in 2013, as an attractive interaction between an electrophilic region on a halogen atom (halogen-bond donor) and a nucleophilic region on another atom or molecule (halogen-bond acceptor) (Desiraju et al., 2013[Desiraju, G. R., Ho, P. S., Kloo, L., Legon, A. C., Marquardt, R., Metrangolo, P., Politzer, P., Resnati, G. & Rissanen, K. (2013). Pure Appl. Chem. 85, 1711-1713.]). The electrophilic region is referred to as the σ hole and is located at the `cap' on the halogen end of the covalent bond, and is accompanied by a `belt' of relatively higher electrostatic potential orthogonal to the bond (Murray et al., 2009[Murray, J. S., Lane, P. & Politzer, P. (2009). J. Mol. Model. 15, 723-729.]; Politzer et al., 2010[Politzer, P., Murray, J. S. & Clark, T. (2010). Phys. Chem. Chem. Phys. 12, 7748-7757.]; Politzer & Murray, 2017[Politzer, P. & Murray, J. S. (2017). Crystals, 7, 212-226.]). A similar electron density distribution is observed for the chalcogen atoms and is particularly pronounced for thio­nes and selones (Vogel et al., 2019[Vogel, L., Wonner, P. & Huber, S. M. (2019). Angew. Chem. Int. Ed. 58, 1880-1891.]). If the chalcogen atoms of these functional groups act as halogen-bond acceptors, the location of the higher electrostatic potential drives the halogen bond away from the terminus of the thione or selone double bond. Conversely, a chalcogen bond, an interaction analogous to a halogen bond involving the σ hole of a chalcogen atom, can occur at the terminus of the thione or selone double bond (Aakeroy et al., 2019[Aakeroy, C. B., Bryce, D. L., Desiraju, G. R., Frontera, A., Legon, A. C., Nicotra, F., Rissanen, K., Scheiner, S., Terraneo, G., Metrangolo, P. & Resnati, G. (2019). Pure Appl. Chem. 91, 1889-1892.]).

As halogen-bond acceptor atoms, nitro­gen and oxygen have received considerably more attention than the heavier chalcogens. For example, a survey of the Cambridge Structural Database (CSD, Version 5.42, update 3; Groom et al., 2016[Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171-179.]), limited to organics, yields 918 results involving an N⋯I halogen bond (where the N⋯I distance is less than the sum of the van der Waals radii of the two atoms) to a pyridine-based nitro­gen atom. A similar search with urea-, thio­urea- or seleno­urea-based acceptors yields 36, 100 and 19 results, respectively. Amongst the limited published data involving Se⋯I interactions, the oxidative addition of interhalogens to diselones, resulting in I—Se—X hypervalent systems is notable (Juárez-Pérez et al., 2011[Juárez-Pérez, E. J., Aragoni, M. C., Arca, M., Blake, A. J., Devillanova, F. A., Garau, A., Isaia, F., Lippolis, V., Núñez, R., Pintus, A. & Wilson, C. (2011). Chem. Eur. J. 17, 11497-11514.]). Our group has been particularly interested in the cooperation of halogen and chalcogen bonding as a versatile crystal engineering tool (Peloquin, McMillen et al., 2021a,[Peloquin, A. J., McMillen, C. D., Iacono, S. T. & Pennington, W. T. (2021a). ChemPlusChem, 86, 549-557.]b[Peloquin, A., McMillen, C. D., Iacono, S. T. & Pennington, W. T. (2021b). Chem. Eur. J. 27, 8398-8405.]; Peloquin, McCollum et al., 2021[Peloquin, A. J., McCollum, J. M., McMillen, C. D. & Pennington, W. T. (2021). Angew. Chem. Int. Ed. 60, 22983-22989.]; Peloquin, Alapati et al., 2021[Peloquin, A. J., Alapati, S., McMillen, C. D., Hanks, T. W. & Pennington, W. T. (2021). Molecules, 26, 4985-4994.]).

Motivated by the lack of published structural data involving halogen bonds to thio­ureas, and especially seleno­ureas, this work serves to further catalog the intermolecular interactions of these functionalities with common organoiodine compounds (Scheme 1[link] shows the organic halogen-bond acceptors and donors utilized in this study), as well as to investigate their reactivity and resulting halogen bonding with molecular diiodine.

[Scheme 1]

To this end, the sterically encumbered diazepine chalcogenone derivatives hexa­hydro-1,3-bis­(2,4,6-tri­methyl­phenyl)-2H-1,3-diazepine-2-thione (SDiazMesS) and hexa­hydro-1,3-bis­(2,4,6-tri­methyl­phenyl)-2H-1,3-diazepine-2-selone (SDiazMesSe) were prepared, the latter of which has not yet been reported in the synthetic literature, and structurally characterized. These were subsequently utilized as halogen-bond acceptors, to explore their halogen bonding tendencies. Each of these parent molecules was reacted with molecular diiodine, which depending on reaction stoichiometry and solvent choice, provided a variety of C=S—I—I, C=Se—I—I and C=Se—I derivatives. When acetone was utilized as the reaction solvent with I2, new S—C, Se—C and C—C bonds were formed via oxidation by I2. Utilizing the six most common commercially available halogen bond donors, 1,2-di­iodo­tetra­fluoro­benzene (1,2-F4DIB), 1,3-di­iodo­tetra­fluoro­benzene (1,3-F4DIB), 1,4-di­iodo­tetra­fluoro­benzene (1,4-F4DIB), 1,3,5-tri­fluoro­tri­iodo­benzene (1,3,5-F3I3B), iodo­penta­fluoro­benzene (IF5B), and tetra­iodo­ethyl­ene (TIE), the molecular structures of 14 new cocrystals were determined. In most cases, the analogous SDiazMesS and SDiazMesSe cocrystals are isomorphic. No significant chalcogen⋯chalcogen (ch⋯ch) or chalcogen⋯iodine (ch⋯I) chalogen bonding or I⋯F halogen bonding is observed within this series of structures.

2. Experimental

2.1. Materials and instrumentation

All reactions were performed under aerobic conditions unless otherwise stated. Solvents were purified and degassed by standard procedures, and all commercially available reagents were used as received. The bis­(mesityl) formamidine MesN = CHNHMes (MesForm) was synthesized as reported (Kuhn & Grubbs, 2008[Kuhn, K. M. & Grubbs, R. H. (2008). Org. Lett. 10, 2075-2077.]) and its corresponding diazepinium bromide derivative (SDiazMesH)Br (Kolychev et al., 2009[Kolychev, E. L., Portnyagin, I. A., Shuntikov, V. V., Khrustalev, V. N. & Nechaev, M. S. (2009). J. Organomet. Chem. 694, 2454-2462.]) was prepared by a modification of a literature procedure (Iglesias et al., 2008[Iglesias, M., Beetstra, D. J., Knight, J. C., Ooi, L. L., Stasch, A., Coles, S., Male, L., Hursthouse, M. B., Cavell, K. J., Dervisi, A. & Fallis, I. A. (2008). Organometallics, 27, 3279-3289.]). 1H and 13C NMR spectra were obtained on Jeol ECX-300 (300 MHz) or Jeol ECA-500 (500 MHz) FT spectrometers. Chemical shifts are reported in p.p.m. relative to SiMe4 (δ = 0 p.p.m.) and were referenced internally with respect to the solvent resonances (1H: δ 2.05 for d5-acetone; 13C: δ 29.84 for (CD3)2CO; coupling constants are given in hertz (Hz). IR spectra were recorded on a PerkinElmer Spectrum 100 spectrometer using an attenuated total reflectance (ATR) accessory and are reported in cm−1; relative intensities of the absorptions are indicated in parentheses (v = very strong, s = strong, m = medium, w = weak). Elemental analyses were determined by Atlantic Microlab, Inc. (Norcross, GA, USA).

For single-crystal X-ray analysis, crystals were mounted on low-background cryogenic loops using paratone oil. Data were collected at 100 K using Mo Kα radiation (λ = 0.71073 Å) on a Bruker D8 Venture diffractometer with an Incoatec Iµs microfocus source and a Photon 2 detector. Diffraction data were collected using φ and ω scans and subsequently processed and scaled using the APEX3 (SAINT/SADABS) (Bruker, 2017[Bruker (2017). APEX3, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) software. The structures were solved with the SHELXT structure solution program and refined utilizing SHELXL, both incorporated in the OLEX2 (v1.5) program package (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. A71, 3-8.],a[Sheldrick, G. M. (2015a). Acta Cryst. C71, 3-8.]; Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]). Hydrogen atoms were placed in geometrically optimized positions using the appropriate riding models. In (SDiazMesS)·(MeCN), (SDiazMesSe)·(MeCN), (SDiazMesS)·(1,3-F4DIB), (SDiazMesSe)·(1,3-F4DIB), 2(SDiazMesS)·(1,3-F4DIB), (SDiazMesS)·(1,3,5-F3I3B), 2(SDiazMesS)·(TIE) and 2(SDiazMesSe)·(TIE), positional disorder of the C—C—C—C portion of the diazepine ring and/or a mesityl substituent was modeled in two parts, utilizing the SIMU restraint as appropriate.

2.2. Preparation of SDiazMesS and SDiazMesSe

The bis­(mesityl)formamidine MesN = CHNHMes (MesForm) was synthesized as reported (Kuhn & Grubbs, 2008[Kuhn, K. M. & Grubbs, R. H. (2008). Org. Lett. 10, 2075-2077.]) and its corresponding diazepinium bromide derivative (SDiazMesH)Br, SDiazMesS and SDiazMesSe were prepared by a modification of literature procedures (Iglesias et al., 2008[Iglesias, M., Beetstra, D. J., Knight, J. C., Ooi, L. L., Stasch, A., Coles, S., Male, L., Hursthouse, M. B., Cavell, K. J., Dervisi, A. & Fallis, I. A. (2008). Organometallics, 27, 3279-3289.]; Rais et al., 2016[Rais, E., Flörke, U. & Wilhelm, R. (2016). Z. Naturforsch. Teil B, 71, 667-676.]).

2.2.1. (SDiazMesH)Br

A stirred mixture of 1,4-di­bromo­butane (5.939 g, 27.506 mmol), the formamidine MesForm (7.000 g, 24.963 mmol), and potassium carbonate (1.989 g, 14.392 mmol) in aceto­nitrile (100 ml) was heated to reflux under argon for 24 h. The resulting solution was cooled to room temperature and concentrated under reduced pressure to ∼2 ml to give a very viscous tan-colored residue. Di­chloro­methane (25 ml) was added to the residue and the mixture stirred overnight, facilitating the separation of a fluffy, white precipitate. The resulting suspension was concentrated under reduced pressure to half volume, treated with cold di­ethyl ether (60 ml), and the sticky, peach-colored product was isolated by vacuum filtration and dried in vacuo for 24 h (7.820 g, 72%). 1H NMR data (in CDCl3): δ 2.27 (s, 6H, CH3), 2.41 (s, 12H, CH3), 2.56 (m, 4H, CH2), 4.65 (m, 4H, CH2), 6.94 (s, 4H, C6H2), 7.21 (s, 1H, NCHN); 1H NMR data (in d6-acetone): δ 2.28 (s, 6H, CH3), 2.45 (s, 12H, CH3), 2.55 (m, 4H, CH2), 4.52 (m, 4H, CH2), 7.05 (m, 4H, C6H2), 8.13 (s, 1H, NCHN).

2.2.2. SDiazMesS

A stirred mixture of (SDiazMesH)Br (5.106 g, 12.292 mmol), elemental sulfur (0.433 g, 13.506 mmol) and potassium carbonate (2.208 g, 15.976 mmol) in n-propanol (75 ml) was heated to reflux for 48 h. The resulting yellow suspension was concentrated to ∼2 ml under reduced pressure to give a beige viscous residue. The product was extracted into di­chloro­methane (50 ml) and the extract was treated with activated carbon (∼1 g) and filtered. The pale orange filtrate was washed with deionized water (3 × 30 ml), and the organic phase was dried over magnesium sulfate (∼1 g) and filtered. Concentration of the solution under vacuum to ∼1 ml and addition of hexanes (20 ml) led to the precipitation of the pale brown product, which was separated by filtration and dried in vacuo for 24 h (3.543 g, 79%). Mp = 179–181 °C (dec.). NMR data (in d6-acetone): 1H δ 2.09 (m, 4H, CH2), 2.23 (s, 6H, CH3), 2.29 (s, 12H, CH3), 3.90 (m, 4H, CH2), 6.85 (s, 6H, C6H2); 13C δ 19.0 (q, 1JC–H = 126, 4C, CH3), 20.9 (q, 1JC–H = 128, 2C, CH3), 26.4 (t, 1JC–H = 127, 2C, CH2), 55.0 (t, 1JC–H = 138, 2C, NCH2), 130.1 (d, 1JC–H = 164, 4C, Cm in C6H2), 135.5 (s, 4C, Co in C6H2), 136.5 (s, 2C, Cp in C6H2), 145.5 (s, 2C, Cipso in C6H2), C=S not observed. IR data: 3141 (w), 2939 (w), 2916 (m), 2854 (w), 2726 (w), 1679 (w), 1643 (s), 1607 (w), 1551 (w), 1488 (m), 1478 (m), 1465 (s), 1426 (m), 1381 (w), 1369 (m), 1359 (w), 1330 (w), 1308 (s), 1287 (vs), 1267 (m), 1214 (m), 1200 (w), 1182 (w), 1148 (w), 1121 (w), 1102 (w), 1032 (w), 1011 (w), 997 (w), 979 (w), 957 (w), 914 (w), 863 (w), 849 (s), 767 (m), 748 (w), 740 (w), 729 (w), 709 (w). Anal. Calc.: for C23H30N2S: C, 75.4; H, 8.3; N, 7.6; found: C, 76.4; H, 8.2; N, 8.1%. Samples for single-crystal X-ray characterization were obtained from EtOH/DCM or MeCN.

2.2.3. SDiazMesSe

A stirred mixture of (SDiazMesH)Br (7.386 g, 17.779 mmol), gray selenium (1.862 g, 23.582 mmol), and potassium carbonate (3.2190 g, 23.291 mmol) in n-propanol (150 ml) was heated to reflux for 20 h. The resulting dark red-orange suspension was concentrated to ∼2 ml under reduced pressure to give a dark orange solid residue. The product was extracted into di­chloro­methane (30 ml) and the bright yellow-orange extract was washed with DI water (3 × 30 ml). The organic phase was separated, dried over magnesium sulfate (∼1 g), filtered, concentrated under vacuum to ∼1 ml, and treated with cold hexanes (10 ml), leading to the precipitation of flaky, orange-yellow product, which was isolated by vacuum filtration and dried in vacuo for 14 h (4.457 g, 61%). Mp = 188–190 °C (dec.). NMR data (in d6-acetone): 1H δ 2.15 (m, 4H, CH2), 2.23 (s, 6H, CH3), 2.30 (s, 12H, CH3), 3.93 (m, 4H, CH2), 6.86 (s, 6H, C6H2); 13C δ 19.1 (q, 1JC–H = 127, 4C, CH3), 21.0 (q, 1JC–H = 127, 2C, CH3), 25.7 (t, 1JC–H = 128, 2C, CH2), 55.2 (t, 1JC–H = 139, 2C, NCH2), 130.2 (d, 1JC–H = 164, 4C, Cm in C6H2), 135.3 (s, 4C, Co in C6H2), 136.7 (s, 2C, Cp in C6H2), 146.6 (s, 2C, Cipso in C6H2), 186.7 (s, 1C, C=Se). IR data: 2971 (w), 2945 (w), 2916 (w), 2854 (w), 1737 (m), 1676 (w), 1645 (s), 1607 (w), 1550 (w), 1489 (m), 1471 (s), 1430 (m), 1369 (m), 1360 (m), 1331 (m), 1286 (vs), 1275 (w), 1254 (w), 1215 (s), 1203 (w), 1185 (w), 1149 (w), 1121 (w), 1104 (w), 1032 (w), 1012 (w), 998 (w), 981 (w), 902 (w), 864 (w), 850 (s), 775 (w), 755 (w), 743 (w), 707 (w). Anal. Calc.: for C23H30N2Se: C, 66.8; H, 7.3; N, 6.8; found: C, 66.7; H, 7.4; N, 6.7%. Samples for single-crystal X-ray characterization were obtained from EtOH/DCM or MeCN.

2.3. Reaction of SDiazMesS and SDiazMesSe with I2

2.3.1. (SDiazMesS)I2

Di­ethyl ether (10 ml) was added to a mixture of SDiazMesS (0.150 g, 0.409 mmol) and elemental iodine (0.104 g, 0.405 mmol), resulting in the formation, within minutes, of a dark-orange solid and a dark-red solution. After stirring the suspension for 17 h, the product was isolated by filtration and dried in vacuo for 24 h (0.154 g, 61%). Mp = 141–143 °C (dec.). NMR data (in d6-acetone): 1H δ 2.27 (s, 10 H, CH3 + CH2), 2.37 (s, 12H, CH3), 4.12 (s, 4H, CH2) 6.96 (s, 4H, C6H2); 13C δ 18.5 (q, 1JC–H = 127, 4C, CH3), 20.5 (q, 1JC–H = 128, 2C, CH3), 23.7 (t, 1JC–H = 130, 2C, CH2), 54.7 (t, 1JC–H = 143, 2C, CH2), 129.6 (d, 1JC–H = 157, 4C, Cm in C6H2), 133.7 (d, 2JC–H = 6, 4C, Co in C6H2), 136.7 (s, 2C, Cp in C6H2), 142.6 (s, 2C, Cipso in C6H2), 176.3 (s, 1C, C=S). IR data: 2948 (w), 2910 (w), 2868 (w), 2730 (w), 1608 (w), 1506 (s), 1474 (m), 1452 (w), 1432 (m), 1391 (m), 1373 (w), 1365 (w), 1354 (w), 1337 (m), 1306 (s), 1286 (vs), 1270 (vs), 1211 (w), 1202 (w), 1187 (w), 1153 (w), 1105 (w), 1036 (w), 1014 (w), 999 (w), 978 (w), 966 (w), 937 (w), 926 (w), 910 (w), 892 (w), 853 (s), 841 (m), 798 (w), 756 (m), 745 (w), 729 (w), 706 (w). Anal. Calc.: for C23H30I2N2S: C, 44.5; H, 4.9; N, 4.5; found: C, 44.3; H, 4.9; N, 4.5%. Crystals suitable for X-ray diffraction analysis were obtained through the slow evaporation of an ethano­lic solution of the compound.

2.3.2. (SDiazMesSe)I2

A mixture of SDiazMesSe (0.144 g, 0.349 mmol) and elemental iodine (0.093 g, 0.366 mmol) in di­ethyl ether (10 ml) was stirred overnight at room temperature. The resulting reddish-brown suspension was concentrated under reduced pressure to ∼1 ml, treated with di­ethyl ether (5 ml), and the dark orange product was isolated by filtration, washed with di­ethyl ether (2 ml), and dried in vacuo for 18 h (0.210 g, 91%). Mp = 195–198 °C (dec.). 1H NMR data (in d6-acetone): δ 2.28 (s, 3H, CH3), 2.33 (s, 4H, CH2), 2.37 (s, 6H, CH3), 4.22 (s, 4H, CH2), 6.98 (s, 2H, C6H2); 13C NMR data (in d6-DMSO): δ 17.9 (q, 1JC–H = 128, 4C, CH3), 20.0 (q, 1JC–H = 127, 2C, CH2), 22.6 (t, 1JC–H = 131, 2C, CH2), 55.5 (t, 1JC–H = 146, 2C, CH2), 129.5 (d, 1JC–H = 158, 2C, Cm in C6H2), 133.4 (s, 1JC–H = 160, 4C, Co in C6H2), 138.1 (s, 4C, Cp in C6H2), 142.2 (s, 2C, Cipso in C6H3), C=Se not observed. IR data: 2950 (m), 2911 (m), 2854 (w), 2730 (w), 1777 (w), 1739 (w), 1607 (m), 1516 (s), 1474 (s), 1452 (w), 1434 (s), 1392 (m), 1374 (m), 1365 (m), 1355 (w), 1338 (m), 1308 (w), 1293 (vs), 1282 (vs), 1269 (vs), 1261 (vs), 1210 (m), 1189 (m), 1150 (w), 1104 (m), 1035 (m), 998 (m), 979 (w), 957 (w), 938 (w), 923 (w), 896 (w), 853 (s), 739 (m), 704 (w). Anal. Calc.: for C23H30I2N2Se: C, 41.4; H, 4.5; N, 4.2; found: C, 41.1; H, 4.7; N, 4.1%. Crystals suitable for X-ray diffraction analysis were obtained through the slow evaporation of an ethano­lic solution of the compound.

2.4. Preparation of cocrystals

2.4.1. (SDiazMesS)·(1,2-F4DIB)

In a 20 ml glass vial, SDiazMesS (30 mg, 0.082 mmol) and 1,2-F4DIB (33 mg, 0.082 mmol) were dissolved in a 1:1 mixture of ethanol and di­chloro­methane (5 ml) with gentle heating. The solvent was allowed to slowly evaporate under ambient conditions (18–20 °C) until colorless, needle-like crystals were observed.

2.4.2. (SDiazMesS)·(1,3-F4DIB)

Using the same procedure as for (SDiazMesS)·(1,2-F4DIB), SDiazMesS (30 mg, 0.082 mmol) and 1,3-F4DIB (66 mg, 0.16 mmol) were combined to yield colorless, plate-like crystals.

2.4.3. (SDiazMesSe)·(1,3-F4DIB)

Using the same procedure as for (SDiazMesS)·(1,2-F4DIB), SDiazMesSe (30 mg, 0.073 mmol) and 1,3-F4DIB (58 mg, 0.15 mmol) were combined to yield yellow, needle-like crystals.

2.4.4. 2(SDiazMesS)·(1,3-F4DIB)

Using the same procedure as for (SDiazMesS)·(1,2-F4DIB), SDiazMesS (60 mg, 0.16 mmol) and 1,3-F4DIB (33 mg, 0.082 mmol) were combined to yield colorless, needle-like crystals.

2.4.5. 2(SDiazMesSe)·(1,3-F4DIB)

Using the same procedure as for (SDiazMesS)·(1,2-F4DIB), SDiazMesSe (60 mg, 0.15 mmol) and 1,3-F4DIB (29 mg, 0.073 mmol) were combined to yield colorless, needle-like crystals.

2.4.6. 2(SDiazMesS)·(1,4-F4DIB)t and 2(SDiazMesS)·(1,4-F4DIB)m

Using the same procedure as (SDiazMesS)·(1,2-F4DIB), SDiazMesS (60 mg, 0.16 mmol) and 1,4-F4DIB (33 mg, 0.082 mmol) were combined to yield 2(SDiazMesS)·(1,4-F4DIB)t as colorless, needle-like crystals on the sides of the vial and 2(SDiazMesS)·(1,4-F4DIB)m as colorless, plank-like crystals from the bottom surface of the vial.

2.4.7. 2(SDiazMesSe)·(1,4-F4DIB)t

Using the same procedure as (SDiazMesS)·(1,2-F4DIB), SDiazMesSe (60 mg, 0.15 mmol) and 1,4-F4DIB (29 mg, 0.073 mmol) were combined to yield colorless, plank-like crystals.

2.4.8. (SDiazMesS)·(1,3,5-F3I3B)

Using the same procedure as (SDiazMesS)·(1,2-F4DIB), SDiazMesS (30 mg, 0.082 mmol) and 1,3,5-F3I3B (42 mg, 0.082 mmol) were combined to yield colorless, needle-like crystals.

2.4.9. (SDiazMesSe)·(1,3,5-F3I3B)

Using the same procedure as (SDiazMesS)·(1,2-F4DIB), SDiazMesSe (30 mg, 0.073 mmol) and 1,3,5-F3I3B (37 mg, 0.073 mmol) were combined to yield yellow, needle-like crystals.

2.4.10. (SDiazMesS)·(IF5B)

Using the same procedure as (SDiazMesS)·(1,2-F4DIB), SDiazMesS (30 mg, 0.082 mmol) and IF5B (120 mg, 0.41 mmol) were combined to yield colorless, plate-like crystals.

2.4.11. 2(SDiazMesSe)·5(IF5B)

In a 1 ml glass tube, SDiazMesSe (30 mg, 0.073 mmol) was dissolved in IF5B (0.25 ml, 1.8 mmol). The solvent was allowed to slowly evaporate under ambient conditions, yielding yellow, plate-like crystals after approximately one week.

2.4.12. 2(SDiazMesS)·(TIE)

Using the same procedure as for (SDiazMesS)·(1,2-F4DIB), SDiazMesS (60 mg, 0.16 mmol) and TIE (44 mg, 0.082 mmol) were combined to yield yellow, plate-like crystals.

2.4.13. 2(SDiazMesSe)·(TIE)

Using the same procedure as for (SDiazMesS)·(1,2-F4DIB), SDiazMesSe (60 mg, 0.15 mmol) and TIE (39 mg, 0.073 mmol) were combined to yield yellow, block-like crystals.

3. Results and discussion

3.1. Synthesis of SDiazMesS and SDiazMesSe

The N-heterocyclic chalcogenones SDiazMesE (E = S, Se), envisioned to have good solubility in common organic solvents and exhibit simple 1H and 13C NMR spectra to facilitate characterization of products, were synthesized in three steps (Scheme 2[link]).

[Scheme 2]
.

Commercially available 2,4,6-tri­methyl­aniline (mesityl­amine) was reacted neat with tri­ethyl­orthoformate in the presence of a catalytic amount of acetic acid (Kuhn & Grubbs, 2008[Kuhn, K. M. & Grubbs, R. H. (2008). Org. Lett. 10, 2075-2077.]) to produce the bis­(mesityl)formamidine MesN=CHNHMes (MesForm) in ∼80% yield. The formamidine was then reacted with 1,4-di­bromo­butane and potassium carbonate in refluxing aceto­nitrile (Iglesias et al., 2008[Iglesias, M., Beetstra, D. J., Knight, J. C., Ooi, L. L., Stasch, A., Coles, S., Male, L., Hursthouse, M. B., Cavell, K. J., Dervisi, A. & Fallis, I. A. (2008). Organometallics, 27, 3279-3289.]) to generate the diazepinium bromide derivative (SDiazMesH)Br, which was isolated in ∼70% yield. Finally, the diazepinium salt is reacted with either elemental sulfur or gray selenium in the presence of a base (K2CO3) in refluxing n-propanol to form the desired thione and selone products in 60–80% yield. The two chalcogenones were fully characterized by a combination of analytical and spectroscopic techniques, including elemental analysis, IR, and 1H and 13C NMR spectroscopies, and single-crystal X-ray diffraction, as described in the next section.

3.2. Structure of SDiazMesS and SDiazMesSe and their MeCN solvates

The parent compound SDiazMesS crystallizes in the monoclinic space group P21/c, whereas SDiazMesSe crystallizes in the orthorhombic space group Pbca (Fig. 1[link]). The thio­urea and seleno­urea are prominent in the respective structures, with a C=S length of 1.6887 (13) Å and an average C=Se length of 1.850 (4) Å from the two unique molecules in the asymmetric unit (Table 1[link]). Despite the cyclic nature of the molecule's core, the N—C=E (E = S, Se) angle remains at approximately 120°, consistent with that of an isolated thio­urea or seleno­urea molecule (Tomkowiak & Katrusiak, 2018[Tomkowiak, H. & Katrusiak, A. (2018). J. Phys. Chem. C, 122, 5064-5070.]). In SDiazMesS, weak C—H⋯S hydrogen bonds [C⋯S = 3.7030 (15) Å and 3.4858 (14) Å], involving hydrogen atoms of the heterocyclic ring, contribute to the stacking of molecules along the c axis. With two unique molecules in the asymmetric unit of SDiazMesSe, the hydrogen-bonding pattern is more complex. To one selenium atom, weak C—H⋯Se hydrogen bonds [C⋯Se = 3.671 (2) Å and 3.665 (2) Å] are observed to two different molecules, both involving hydrogen atoms of the heterocyclic rings. In both cases, the mesityl rings are nearly perpendicular to the urea plane. For example, in SDiazMesS, the mesityl-to-urea plane angles are 91.46 (4)° and 89.60 (4)°. These geometric parameters remain consistent throughout the variety of cocrystals, adducts, and solvates in this study. Unlike the unsolvated structures of the parent molecules, the aceto­nitrile solvates (SDiazMesS)·(MeCN) and (SDiazMesSe)·(MeCN) are isomorphous, with a weak hydrogen bonding interaction observed between the chalcogen atom and the aceto­nitrile molecule.

Table 1
Selected bond lengths (Å) in SDiazMesE, (SDiazMesE)·(MeCN) (E = S, Se) and the products of reaction with I2

Compound dC=E dC—N E—I I—I
SDiazMesS 1.6887 (13) 1.3625 (16) 1.361 (2)
SDiazMesSe 1.851 (2) 1.361 (3) 1.348 (3)
1.850 (2) 1.356 (3) 1.353 (3)
(SDiazMesS)·(MeCN) 1.6821 (15) 1.3627 (17) 1.3689 (15)
(SDiazMesSe)·(MeCN) 1.8498 (18) 1.355 (2) 1.3586 (19)
SDiazMesS—I2 1.738 (3) 1.356 (4) 1.337 (5) 2.6738 (9) 2.8794 (4)
SDiazMesSe—I2 1.8973 (16) 1.334 (3) 1.351 (2) 2.7559 (4) 2.9106 (4)
(SDiazMesS—I2)·(I2) 1.7555 (18) 1.335 (3) 1.344 (2) 2.5052 (5) 3.0803 (4)
[(SDiazMesSe—I)(I3)] 1.921 (10) 1.338 (13) 1.339 (13) 2.5807 (14) 3.2052 (10)
[(SDiazMesSe—I)(I3)]·(DCM) 1.9274 (17) 1.331 (3) 1.338 (3) 2.5958 (3) 3.1867 (3)
[(SDiazMesSe-DMK)(I3)]·(I2) 1.910 (9) 1.320 (12) 1.336 (11)
[(SDiazMesS-MIBK)(I3)] 1.772 (4) 1.339 (4) 1.329 (4)
[(SDiazMesSe-MIBK)(I3)] 1.9284 (17) 1.340 (3) 1.328 (2)
[Figure 1]
Figure 1
Views of the molecular structures of SDiazMesS (left-hand view) and SDiazMesSe (right-hand view). Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms are omitted for clarity.

3.3. Reaction of SDiazMesS and SDiazMesSe with I2

The reaction of molecular iodine with SDiazMesS and SDiazMesSe provided a rich series of products depending on the ratio of I2 to thione or selone and the solvent choice (Scheme 3[link]).

[Scheme 3]

The reaction of SDiazMesS or SDiazMesSe with a stoichiometric amount of I2 in di­ethyl ether provides SDiazMesS-I2 or SDiazMesSe-I2, both crystallizing in the triclinic space group [P{\bar 1}]. In both cases, short chalcogen⋯iodine distances are observed [S—I = 2.6738 (9) Å and Se—I = 2.7559 (4) Å], with concomitant lengthening of the I—I bond to 2.8794 (4) Å in SDiazMesS-I2 and 2.9106 (4) Å in SDiazMesSe-I2. These I—I distances correspond to bond orders of 0.59 and 0.53, respectively, as calculated using the expression of Pauling, D(n′) = D(1) − 0.71 log (n′) with a D(1) of 2.72 Å (Pauling, 1960[Pauling, L. (1960). The Nature of the Chemical Bond. Ithaca, NY: Cornell University Press.]). A series of weak C—H⋯I hydrogen bonds consolidate the packing.

The reaction with 2.5 molar equivalents of I2 in a 1:1 mixture of ethanol and di­chloro­methane provides different products from SDiazMesS and SDiazMesSe. When the reaction was conducted with SDiazMesS, the cocrystal (SDiazMesS—I2)·(I2) was obtained in the triclinic space group [P{\bar 1}]. The bond distances within the S—I—I fragment are reduced from those in SDiazMesS, with the S—I distance shrinking to 2.5052 (5) Å while the I–I distance further elongates to 3.0803 (4) Å. This change in bond geometries is indicative of further progression towards the dipolar I+⋯I extreme, with a calculated bond order of 0.31. The consolidation of the negative charge on the terminal iodine atom of the S—I—I fragment contributes to its increased ability to serve as a halogen-bond acceptor. The incorporation of a diiodine molecule within the structure aids in the formation of chains in the [[0{\bar 1}1]] direction through I⋯I halogen bonding. There are two such unique I⋯I halogen bonds formed at each terminal iodine atom of the S—I—I, both of which are similar in length [I⋯I = 3.4171 (4) Å and 3.4694 (5) Å]. In contrast to the reaction of SDiazMesS with excess I2, the reaction of 2.5 molar equivalents of I2 with SDiazMesSe in 1:1 ethanol:dichloromethane provides the salt [(SDiazMesSe—I)(I3)]. Crystalline [(SDiazMesSe—I)(I3)] forms within five minutes, and if this material is recrystallized from di­chloro­methane, the crystalline solvate [(SDiazMesSe—I)(I3)]·(DCM) is obtained. In both cases, the Se—I—I fragment is better represented as (Se—I+)(I3). This assignment is supported by the further contraction of the Se–I distance to 2.5807 (14) Å and expansion of the I+⋯I distance to 3.2052 (10) Å relative to SDiazMesSe—I2. This I⋯I distance would correspond to a calculated bond order of only 0.20. The C=Se length remains relatively unchanged [1.921 (10) Å] compared to SDiazMesSe—I2 (1.8973 (16) Å. The triiodide anion in both salts is asymmetric, with the two I—I lengths of 3.0222 (10) Å and 2.8492 (10) Å in [(SDiazMesSe—I)(I3)] and 3.0098 (6) Å and 2.8426 (6) Å in [(SDiazMesSe—I)(I3)]·(DCM). This degree of asymmetry is in line with other reported triiodide salts (Kobra et al., 2018[Kobra, K., O'Donnell, S., Ferrari, A., McMillen, C. D. & Pennington, W. T. (2018). New J. Chem. 42, 10518-10528.]). In [(SDiazMesSe—I)(I3)], halogen bonding does not contribute to the long-range packing motif, beyond the aforementioned connection of one end of I3 to the Se—I fragment; however, in [(SDiazMesSe—I)(I3)]·(DCM), a combination of I⋯I halogen bonding and Se⋯I chalcogen bonding contributes to the formation of chains along the a axis (Fig. 2[link]).

[Figure 2]
Figure 2
Views of the molecular structures of the products of the reaction of I2 with SDiazMesS and SDiazMesSe in non-acetone solvents. Intermolecular I⋯I and Se⋯I interactions are indicated by magenta and black dotted lines, respectively. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms are omitted for clarity.

The use of acetone as the reaction solvent allowed access to new organic products resulting from forming a new covalent bond between the chalcogen atom and a methyl carbon of acetone (Fig. 3[link]). When the reaction of SDiazMesSe and 2.5 molar equivalents of diiodine was conducted in acetone, the salt [(SDiazMesSe-DMK)(I3)]·(I2) was obtained, displaying an added di­methyl­ketone (DMK) fragment, resulting from the diiodine-promoted addition of an acetone molecule to the selenium atom. The slight elongation of the C=Se bond and negligible change in the C—N lengths suggest the positive charge is primarily localized to the selenium atom (Table 1[link]). If a 1:1 mixture of ethanol and acetone was utilized as the reaction solvent for the reaction with 2.5 molar equivalents of I2, the isomorphic products [(SDiazMesS-MIBK)(I3)] and [(SDiazMesSe-MIBK)(I3)] were obtained, both crystallizing in the triclinic space group [P{\bar 1}]. The methyl­iso­butyl­ketone (MIBK) fragment bound to the chalcogen atom results from the further bond formation of the methyl carbon of [(SDiazMesSe-DMK)(I3)]·(I2) with the carbonyl carbon of an additional acetone molecule along with de­oxy­genation. A related reaction involving the addition of acetone to a sulfur atom in 1,4-di­thiane has been previously reported (Peloquin, Alapati et al., 2021[Peloquin, A. J., Alapati, S., McMillen, C. D., Hanks, T. W. & Pennington, W. T. (2021). Molecules, 26, 4985-4994.]). Just as in [(SDiazMesSe-DMK)(I3)]·(I2), the only slight lengthening of C—S and C—Se distances, along with a negligible change in C—N distances, relative to the parent molecule indicate the positive charge is primarily localized on the chalcogen atom. The triiodide anion is pinned in place by weak type I halogen bonds with the I2 molecule. While all attempts to isolate the analogous SDiazMesS-containing structure to [(SDiazMesSe-DMK)(I3)]·(I2) were unsuccessful, the isolation of [(SDiazMesS-MIBK)(I3)] does suggest its formation occurs. Adding ethanol to the reaction mixture reduces the overall solvent polarity and likely supports the solubility of the increased aliphatic character of the MIBK fragment over DMK.

[Figure 3]
Figure 3
Views of the molecular structures of the products of the reaction of I2 with SDiazMesS and SDiazMesSe in acetone. Intermolecular I⋯I interactions are indicated by magenta dotted lines. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms are omitted for clarity.

3.4. Cocrystallization of SDiazMesS and SDiazMesSe with iodo­fluoro­benzenes

The cocrystal (SDiazMesS)·(1,2-F4DIB) crystallizes in the orthorhombic space group Pna21 with one molecule each of SDiazMesS and 1,2-F4DIB within the asymmetric unit (Fig. 4[link]). C—I⋯S halogen bonding occurs between the thione sulfur atom and only one iodine atom of 1,2-F4DIB, leading to the formation of discrete halogen bonded dimers. The halogen-bond distance in this cocrystal, 3.2092 (12) Å, is significantly shorter than measured in the ternary cocrystal of thio­urea, 1,2-F4DIB, and 18-crown-6 [3.4680 (6) Å] (Topić & Rissanen, 2016[Topić, F. & Rissanen, K. (2016). J. Am. Chem. Soc. 138, 6610-6616.]). The lack of I⋯S halogen bonding to the second iodine atom is likely due to a combination of the steric bulk of SDiazMesS and the proximity of the iodine atoms in 1,2-F4DIB. Neighboring dimers consolidate through a combination of weak C—H⋯I and C—H⋯S interactions. All attempts to isolate the corresponding SDiazMesSe cocrystal were unsuccessful.

[Figure 4]
Figure 4
Halogen bonding in (SDiazMesS)·(1,2-F4DIB). Intermolecular I⋯S halogen bonding is indicated by a magenta dotted line. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms are omitted for clarity.

With 1,3-F4DIB as the halogen bond donor, four cocrystalline structures were obtained (Fig. 5[link]). The first two, (SDiazMesS)·(1,3-F4DIB) and (SDiazMesSe)·(1,3-F4DIB), are isomorphic. Both cocrsytals are obtained in the ortho­rhombic space group P212121 with one molecule of either SDiazMesS or SDiazMesSe along with one molecule of 1,3-F4DIB. A pair of nearly identical length C—I⋯S halogen bonds connect SDiazMesS or SDiazMesSe molecules with molecules of 1,3-F4DIB in alternating fashion to form helical chains propagating along the b axis. The packing is consolidated along the a axis by weak C—H⋯π interactions and in the c direction by C—H⋯F interactions, both involving hydrogen atoms of the heterocyclic ring. The addition of a second equivalent of SDiazMesS or SDiazMesSe results in the cocrystals 2(SDiazMesS)·(1,3-F4DIB) and 2(SDiazMesSe)·­(1,3-F4DIB). Just as in the 1:1 cocrystals, the 2:1 cocrystals are isomorphic with one another, crystallizing in the monoclinic space group C2/c. Discrete halogen bonding units are formed with only one halogen bond observed at each chalcogen atom. These units stack along the c axis through ππ stacking of the 1,3-F4DIB rings, with ring plane-to-ring plane distances of 3.2840 (10) Å and 3.3046 (12) Å and slippage of 2.359 Å and 2.337 Å in 2(SDiazMesS)·(1,3-F4DIB) and 2(SDiazMesSe)·(1,3-F4DIB) respectively. These four cocrystals represent the first reported examples of halogen-bonded cocrystals of 1,3-F4DIB with a thio­urea or seleno­urea molecule.

[Figure 5]
Figure 5
Halogen bonding in the 1,3-F4DIB-containing cocrystals. Intermolecular I⋯S and I⋯Se halogen bonding is indicated by magenta dotted lines. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms are omitted for clarity.

The reaction with the common halogen bond donor 1,4-F4DIB yielded two polymorphic structures with SDiazMesS: 2(SDiazMesS)·(1,4-F4DIB)t, which crystallized in the triclinic space group [P{\bar 1}], and 2(SDiazMesS)·(1,4-F4DIB)m which crystallized in the monoclinic space group P21/c. The triclinic isomorph, 2(SDiazMesSe)·(1,4-F4DIB)t, was obtained with SDiazMesSe (Fig. 6[link]). All attempts to isolate the monoclinic isomorph with SDiazMesSe were unsuccessful. In all three cases, a single halogen bond is observed at each chalcogen atom, forming discrete units from two thione or selone molecules and one molecule of 1,4-F4DIB. For the triclinic isomorphs, the halogen-bond geometry is nearly linear, with a C—I⋯S angle of 175.67 (9)° in 2(SDiazMesS)·(1,4-F4DIB)t and a C—I⋯Se angle of 173.97 (4)° in 2(SDiazMesSe)·(1,4-F4DIB)t. The iodine⋯chalcogen distances in these triclinic polymorphs [I⋯S = 3.2318 (7) Å and I⋯Se = 3.2553 (3) Å] are shorter than the analogous cocrystals with thio­urea [I⋯S = 3.287 (12) Å] or seleno­urea [I⋯Se = 3.3151 (17) Å] (Arman et al., 2010[Arman, H. D., Gieseking, R. L., Hanks, T. W. & Pennington, W. T. (2010). Chem. Commun. 46, 1854-1856.]; Chernysheva & Haukka, 2021[Chernysheva, M. V. & Haukka, M. (2021). J. Solid State Chem. 293, 121759.]). Weak chalcogen⋯hydrogen interactions contribute to the stacking of these discrete units along the a axis. In the monoclinic polymorph, while the discrete 2:1 halogen bonding units are maintained, the C—I⋯S halogen bond is elongated relative to the triclinic polymorph, and deviates significantly from linearity [143.57 (6)°]. This geometric arrangement may suggest an intermediate between true halogen and chalcogen bonds. The (C—)I iodine atom is also involved in a weak I⋯π interaction [3.646 (2) Å]. The repositioning of the 1,4-F4DIB between the two SDiazMesS molecules in the monoclinic polymorph compared to the triclinic polymorph enable the iodine atoms to be involved in weak I⋯π interactions [3.646 (2) Å].

[Figure 6]
Figure 6
Halogen bonding in the 1,4-F4DIB-containing cocrystals. Intermolecular I⋯S and I⋯Se halogen bonding is indicated by magenta dotted lines. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms are omitted for clarity.

While the di­iodo­tetra­fluoro­benzene-containing cocrystal systems discussed thus far show roughly equivalent behavior between sulfur and selenium, the 1,3,5-F3I3B cocrystals (SDiazMesS)·(1,3,5-F3I3B) and (SDiazMesSe)·(1,3,5-F3I3B) do display a subtle, but important difference (Fig. 7[link]). In this pair, the structures are not isomorphic, with (SDiazMesS)·(1,3,5-F3I3B) crystallizing in the monoclinic space group P21/c and (SDiazMesSe)·(1,3,5-F3I3B) in space group P21/n. In both cases, a pair of iodine⋯chalcogen halogen bonds are observed at each chalcogen atom. Each of these interactions ranges in normalized distance parameter, RXB, from 0.85 to 0.92. The third iodine atom of each 1,3,5-F3I3B molecule drives the differences in the overall packing motif. Of the three symmetry unique 1,3,5-F3I3B molecules in (SDiazMesS)·(1,3,5-F3I3B), the third iodine atom of two of these (I2 and I8) have the appropriate geometric orientation to participate in a C—I⋯S halogen bond [C—I⋯S = 170.5 (2)° and 177.9 (2)°], but the iodine⋯sulfur distance is well beyond the sum of the van der Waals radii (RXB = 1.12 and 1.14). This series of interactions contributes to the formation of ring-link units consisting of six SDiazMesS and six 1,3,5-F3I3B molecules. The third iodine atom of the final symmetry unique 1,3,5-F3I3B molecule participates in a weak type I, I⋯I interaction. In (SDiazMesSe)·(1,3,5-F3I3B), two primary C—I⋯Se halogen bonds (RXB = 0.90 and 0.92) again occur at each selenium atom. However, the third iodine atom of each 1,3,5-F3I3B molecule drives a difference in the overall packing motif. In this case, a weak C—I⋯Se halogen bond occurs roughly at the sum of the van der Waals radii (RXB = 1.01). This weak contact, probably enabled by the increased van der Waals radius of selenium over sulfur, and therefore decreased steric congestion around the chalcogen atom, is enough to consolidate the halogen bonding motif into a ladder-like chain propagating in the c direction. These two cocrystals represent the first reported examples of halogen-bonded cocrystals of 1,3,5-F3I3B with a thio­urea or seleno­urea.

[Figure 7]
Figure 7
Halogen bonding in the 1,3,5-F3I3B-containing cocrystals. Intermolecular I⋯S and I⋯Se halogen bonding is indicated by magenta dotted lines. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms are omitted for clarity.

With the halogen bond donor iodo­penta­fluoro­benzene (IF5B), different reaction conditions were required for SDiazMesS and SDiazMesSe, resulting in dramatically different cocrystalline structures (Fig. 8[link]). By reacting five equivalents of IF5B with SDiazMesS in ethanol, (SDiazMesS)·(IF5B) was obtained in the orthorhombic space group Pna21. A single I⋯S halogen bond is observed at each sulfur atom. The halogen bond length [I⋯S = 3.1809 (14) Å] is comparable to that measured in the ternary cocrystal of IF5B, thio­urea, and 18-crown-6 [I⋯S = 3.1977 (14) Å] (Topić & Rissanen, 2016[Topić, F. & Rissanen, K. (2016). J. Am. Chem. Soc. 138, 6610-6616.]). These halogen bonded pairs stack along the a axis through ππ stacking of the IF5B molecules, with a centroid to centroid distance between rings of 3.0340 (19) Å and slippage of 2.925 Å. The reaction conditions which produced (SDiazMesS)·(IF5B) did not yield the analogous cocrystal with SDiazMesSe. To force cocrystallization, SDiazMesSe was dissolved in neat IF5B, resulting in the cocrystal 2(SDiazMesSe)·5(IF5B). This cocrystal was obtained in the monoclinic space group P21/c. In contrast to (SDiazMesS)·(IF5B), in which only one halogen bond is observed to each chalcogen atom, two I⋯Se halogen bonds are observed to each selenium atom in 2(SDiazMesSe)·5(IF5B). The length of these halogen bonds [I⋯Se = 3.2808 (5) Å and 3.3211 (7) Å] are comparable to the analogous distance in the reported cocrystal of IF5B and 1,1-di­methyl­seleno­urea [I⋯Se = 3.2841 (12) Å] (Chernysheva et al., 2021[Chernysheva, M. V., Rautiainen, J. M., Ding, X. & Haukka, M. (2021). J. Solid State Chem. 295, 121930. ]). The halogen bonds are similar when normalized for the increased van der Waals radius of selenium versus sulfur. The packing is consolidated along the a axis through weak C—F⋯π interactions.

[Figure 8]
Figure 8
Halogen bonding in (SDiazMesS)·(IF5B) and 2(SDiazMesSe)·5(IF5B). Intermolecular I⋯S and I⋯Se halogen bonding is indicated by magenta dotted lines. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms are omitted for clarity.

3.5. Cocrystallization of SDiazMesS and SDiazMesSe with tetra­iodo­ethyl­ene

The final pair of cocrystals, 2(SDiazMesS)·(TIE) and 2(SDiazMesSe)·(TIE), are both obtained in the triclinic space group [P{\bar 1}], with one thione or selone molecule and one half of a TIE molecule per asymmetric unit. A single halogen bond is observed to the chalcogen atom, contributing to discrete 2:1 units within the structure (Fig. 9[link]). The remaining two iodine atoms of each TIE molecule appear to be pinned in place by weak C—H⋯I interactions from methyl groups of three neighboring SDiazMesE molecules, contributing to the formation of ribbons in the bc plane.

[Figure 9]
Figure 9
Halogen bonding in the TIE-containing cocrystals. Intermolecular I⋯S and I⋯Se halogen bonding is indicated by magenta dotted lines. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms are omitted for clarity.

4. Conclusions

The heterocyclic molecules hexa­hydro-1,3-bis­(2,4,6-tri­methyl­phenyl)-2H-1,3-diazepine-2-thione and hexa­hydro-1,3-bis­(2,4,6-tri­methyl­phenyl)-2H-1,3-diazepine-2-selone provided a robust template for halogen and/or chalcogen bonding interactions, yielding a total of 24 new cocrystal structures. The reaction with molecule diiodine provided products incorporating S—I—I and Se—I—I fragments with a wide range of bond orders. When this reaction was conducted in acetone, oxidative addition of acetone to the chalcogen atom allowed the formation of new C—S, C—Se and C—C covalent bonds under mild conditions. Cocrystallization with iodo­penta­fluoro­benzene, 1,2-, 1,3- and 1,4-di­iodo­tetra­fluoro­benzene, 1,3,5-tri­fluoro­tri­iodo­benzene, and tetra­iodo­ethyl­ene reveals structures that, in most cases, show a preference for halogen over chalcogen bonding and are typically isomorphic. This series of structural data supports the power of crystallographic study to reveal unexpected and unique interactions and reaction pathways.

Supporting information


Computing details top

For all structures, data collection: APEX3 v2017.3-0 (Bruker AXS Inc., 2017); cell refinement: SAINT V8.38A (Bruker AXS Inc., 2017); data reduction: SAINT V8.38A (Bruker AXS Inc., 2017); program(s) used to solve structure: SHELXT 2018/2 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL 2018/3 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: Olex2 1.5 (Dolomanov et al., 2009).

(SDiazMesS) top
Crystal data top
C23H30N2SF(000) = 792
Mr = 366.55Dx = 1.186 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 16.4064 (14) ÅCell parameters from 9938 reflections
b = 8.7386 (9) Åθ = 2.6–27.9°
c = 14.8229 (14) ŵ = 0.17 mm1
β = 104.983 (3)°T = 100 K
V = 2052.9 (3) Å3Block, colourless
Z = 40.30 × 0.19 × 0.17 mm
Data collection top
Bruker D8 Venture Photon 2
diffractometer
3717 reflections with I > 2σ(I)
Radiation source: Incoatec IµSRint = 0.044
φ and ω scansθmax = 26.5°, θmin = 2.6°
Absorption correction: multi-scan
SADABS v2016/2 (Bruker AXS Inc., 2017)
h = 2019
Tmin = 0.706, Tmax = 0.746k = 1010
33473 measured reflectionsl = 1818
4240 independent reflections
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0371P)2 + 1.5577P]
where P = (Fo2 + 2Fc2)/3
4240 reflections(Δ/σ)max = 0.001
241 parametersΔρmax = 0.37 e Å3
0 restraintsΔρmin = 0.27 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
S10.69533 (2)0.74837 (4)0.29532 (2)0.01726 (10)
N10.80101 (7)0.72854 (13)0.46402 (8)0.0151 (2)
C10.71991 (8)0.75052 (14)0.41320 (9)0.0139 (3)
C20.82151 (9)0.67659 (17)0.56223 (9)0.0190 (3)
H2A0.8758340.6206790.5767170.023*
H2B0.7773320.6047240.5704190.023*
N20.65924 (7)0.77220 (13)0.45957 (8)0.0149 (2)
C30.82787 (9)0.80908 (19)0.63033 (10)0.0226 (3)
H3A0.8795400.8690830.6325590.027*
H3B0.8317650.7688770.6937440.027*
C40.75048 (9)0.91216 (17)0.59967 (10)0.0210 (3)
H4A0.7434200.9710970.6541880.025*
H4B0.7596870.9860480.5526460.025*
C50.67010 (9)0.82163 (17)0.55817 (9)0.0184 (3)
H5A0.6699150.7296420.5970990.022*
H5B0.6210090.8852050.5614720.022*
C70.89749 (8)0.57991 (16)0.39698 (9)0.0170 (3)
C60.86912 (8)0.72241 (16)0.41884 (9)0.0157 (3)
C91.00943 (9)0.70720 (19)0.34508 (10)0.0213 (3)
C80.96802 (9)0.57501 (17)0.36037 (9)0.0196 (3)
H80.9880790.4786460.3455990.024*
C100.97800 (9)0.84722 (17)0.36537 (10)0.0201 (3)
H101.0048960.9385710.3535510.024*
C110.90822 (9)0.85794 (16)0.40253 (9)0.0175 (3)
C120.85341 (9)0.43400 (17)0.41083 (11)0.0228 (3)
H12A0.8764950.3967820.4747100.034*
H12B0.8621680.3566450.3663910.034*
H12C0.7928650.4536020.4003950.034*
C131.08734 (10)0.6999 (2)0.30884 (13)0.0324 (4)
H13A1.1373140.7218300.3598700.049*
H13B1.0828650.7757770.2591100.049*
H13C1.0923810.5973900.2840350.049*
C140.87597 (10)1.01221 (17)0.42238 (10)0.0233 (3)
H14A0.9147171.0919850.4124260.035*
H14B0.8722741.0156140.4872850.035*
H14C0.8199161.0294860.3803500.035*
C150.57190 (8)0.75149 (16)0.40930 (9)0.0151 (3)
C160.52152 (9)0.87994 (16)0.37804 (9)0.0166 (3)
C170.43675 (9)0.85616 (17)0.33349 (10)0.0199 (3)
H170.4016930.9418730.3112400.024*
C180.40206 (9)0.70968 (18)0.32076 (10)0.0223 (3)
C190.45411 (9)0.58466 (17)0.35178 (10)0.0210 (3)
H190.4309900.4844700.3424040.025*
C200.53954 (9)0.60283 (16)0.39638 (9)0.0176 (3)
C210.55692 (9)1.03973 (16)0.39057 (10)0.0217 (3)
H21A0.5204131.1081310.3451740.033*
H21B0.6137241.0397690.3807160.033*
H21C0.5596521.0753160.4539810.033*
C220.30947 (10)0.6871 (2)0.27393 (14)0.0358 (4)
H22A0.2980310.5779580.2617970.054*
H22B0.2946320.7434690.2147580.054*
H22C0.2756990.7253700.3148510.054*
C230.59506 (10)0.46490 (17)0.42671 (11)0.0235 (3)
H23A0.5597680.3738040.4245440.035*
H23B0.6297140.4802960.4906220.035*
H23C0.6317890.4509470.3846700.035*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.01580 (18)0.0250 (2)0.01103 (17)0.00180 (13)0.00354 (13)0.00034 (13)
N10.0139 (5)0.0195 (6)0.0125 (5)0.0013 (4)0.0040 (4)0.0016 (4)
C10.0159 (6)0.0117 (6)0.0144 (6)0.0006 (5)0.0042 (5)0.0001 (5)
C20.0166 (6)0.0254 (7)0.0145 (6)0.0021 (6)0.0031 (5)0.0054 (6)
N20.0134 (5)0.0200 (6)0.0113 (5)0.0009 (4)0.0029 (4)0.0024 (4)
C30.0186 (7)0.0353 (8)0.0132 (6)0.0041 (6)0.0028 (5)0.0007 (6)
C40.0226 (7)0.0249 (7)0.0159 (7)0.0040 (6)0.0056 (5)0.0050 (6)
C50.0189 (7)0.0257 (7)0.0117 (6)0.0007 (6)0.0058 (5)0.0028 (5)
C70.0147 (6)0.0204 (7)0.0147 (6)0.0007 (5)0.0015 (5)0.0010 (5)
C60.0127 (6)0.0214 (7)0.0125 (6)0.0003 (5)0.0025 (5)0.0008 (5)
C90.0140 (6)0.0335 (8)0.0162 (7)0.0012 (6)0.0032 (5)0.0034 (6)
C80.0165 (7)0.0245 (7)0.0174 (7)0.0047 (6)0.0033 (5)0.0002 (6)
C100.0168 (7)0.0252 (7)0.0174 (7)0.0043 (6)0.0027 (5)0.0035 (6)
C110.0165 (6)0.0207 (7)0.0137 (6)0.0007 (5)0.0010 (5)0.0006 (5)
C120.0238 (7)0.0192 (7)0.0267 (8)0.0003 (6)0.0088 (6)0.0008 (6)
C130.0237 (8)0.0416 (10)0.0369 (9)0.0030 (7)0.0168 (7)0.0054 (8)
C140.0270 (8)0.0193 (7)0.0236 (7)0.0023 (6)0.0066 (6)0.0003 (6)
C150.0138 (6)0.0204 (7)0.0120 (6)0.0006 (5)0.0049 (5)0.0011 (5)
C160.0182 (7)0.0192 (7)0.0141 (6)0.0007 (5)0.0071 (5)0.0013 (5)
C170.0182 (7)0.0241 (7)0.0172 (7)0.0058 (6)0.0044 (5)0.0034 (6)
C180.0164 (7)0.0307 (8)0.0202 (7)0.0009 (6)0.0056 (6)0.0075 (6)
C190.0192 (7)0.0221 (7)0.0233 (7)0.0053 (6)0.0085 (6)0.0059 (6)
C200.0183 (7)0.0195 (7)0.0162 (6)0.0004 (5)0.0068 (5)0.0012 (5)
C210.0237 (7)0.0183 (7)0.0237 (7)0.0001 (6)0.0069 (6)0.0007 (6)
C220.0169 (8)0.0397 (10)0.0479 (11)0.0001 (7)0.0030 (7)0.0153 (8)
C230.0259 (7)0.0180 (7)0.0264 (8)0.0000 (6)0.0066 (6)0.0009 (6)
Geometric parameters (Å, º) top
S1—C11.6887 (14)C12—H12A0.9800
N1—C11.3625 (17)C12—H12B0.9800
N1—C21.4783 (17)C12—H12C0.9800
N1—C61.4447 (17)C13—H13A0.9800
C1—N21.3611 (17)C13—H13B0.9800
C2—H2A0.9900C13—H13C0.9800
C2—H2B0.9900C14—H14A0.9800
C2—C31.522 (2)C14—H14B0.9800
N2—C51.4898 (16)C14—H14C0.9800
N2—C151.4454 (17)C15—C161.3999 (19)
C3—H3A0.9900C15—C201.3977 (19)
C3—H3B0.9900C16—C171.392 (2)
C3—C41.527 (2)C16—C211.505 (2)
C4—H4A0.9900C17—H170.9500
C4—H4B0.9900C17—C181.394 (2)
C4—C51.5245 (19)C18—C191.390 (2)
C5—H5A0.9900C18—C221.511 (2)
C5—H5B0.9900C19—H190.9500
C7—C61.3965 (19)C19—C201.396 (2)
C7—C81.4001 (19)C20—C231.508 (2)
C7—C121.506 (2)C21—H21A0.9800
C6—C111.3974 (19)C21—H21B0.9800
C9—C81.388 (2)C21—H21C0.9800
C9—C101.391 (2)C22—H22A0.9800
C9—C131.510 (2)C22—H22B0.9800
C8—H80.9500C22—H22C0.9800
C10—H100.9500C23—H23A0.9800
C10—C111.3961 (19)C23—H23B0.9800
C11—C141.505 (2)C23—H23C0.9800
C1—N1—C2121.92 (11)C7—C12—H12C109.5
C1—N1—C6120.72 (11)H12A—C12—H12B109.5
C6—N1—C2116.02 (11)H12A—C12—H12C109.5
N1—C1—S1120.55 (10)H12B—C12—H12C109.5
N2—C1—S1120.92 (10)C9—C13—H13A109.5
N2—C1—N1118.52 (12)C9—C13—H13B109.5
N1—C2—H2A109.2C9—C13—H13C109.5
N1—C2—H2B109.2H13A—C13—H13B109.5
N1—C2—C3112.26 (12)H13A—C13—H13C109.5
H2A—C2—H2B107.9H13B—C13—H13C109.5
C3—C2—H2A109.2C11—C14—H14A109.5
C3—C2—H2B109.2C11—C14—H14B109.5
C1—N2—C5128.18 (11)C11—C14—H14C109.5
C1—N2—C15118.63 (11)H14A—C14—H14B109.5
C15—N2—C5113.15 (10)H14A—C14—H14C109.5
C2—C3—H3A109.7H14B—C14—H14C109.5
C2—C3—H3B109.7C16—C15—N2119.48 (12)
C2—C3—C4110.02 (12)C20—C15—N2118.55 (12)
H3A—C3—H3B108.2C20—C15—C16121.94 (13)
C4—C3—H3A109.7C15—C16—C21121.81 (12)
C4—C3—H3B109.7C17—C16—C15117.98 (13)
C3—C4—H4A109.1C17—C16—C21120.21 (13)
C3—C4—H4B109.1C16—C17—H17119.2
H4A—C4—H4B107.9C16—C17—C18121.61 (13)
C5—C4—C3112.33 (12)C18—C17—H17119.2
C5—C4—H4A109.1C17—C18—C22120.58 (14)
C5—C4—H4B109.1C19—C18—C17118.87 (13)
N2—C5—C4114.70 (11)C19—C18—C22120.55 (14)
N2—C5—H5A108.6C18—C19—H19119.2
N2—C5—H5B108.6C18—C19—C20121.55 (14)
C4—C5—H5A108.6C20—C19—H19119.2
C4—C5—H5B108.6C15—C20—C23121.55 (13)
H5A—C5—H5B107.6C19—C20—C15118.04 (13)
C6—C7—C8118.40 (13)C19—C20—C23120.38 (13)
C6—C7—C12121.52 (12)C16—C21—H21A109.5
C8—C7—C12120.07 (13)C16—C21—H21B109.5
C7—C6—N1118.99 (12)C16—C21—H21C109.5
C7—C6—C11121.35 (12)H21A—C21—H21B109.5
C11—C6—N1119.57 (12)H21A—C21—H21C109.5
C8—C9—C10118.20 (13)H21B—C21—H21C109.5
C8—C9—C13121.19 (14)C18—C22—H22A109.5
C10—C9—C13120.61 (14)C18—C22—H22B109.5
C7—C8—H8119.1C18—C22—H22C109.5
C9—C8—C7121.75 (13)H22A—C22—H22B109.5
C9—C8—H8119.1H22A—C22—H22C109.5
C9—C10—H10118.9H22B—C22—H22C109.5
C9—C10—C11122.15 (13)C20—C23—H23A109.5
C11—C10—H10118.9C20—C23—H23B109.5
C6—C11—C14121.68 (12)C20—C23—H23C109.5
C10—C11—C6118.12 (13)H23A—C23—H23B109.5
C10—C11—C14120.19 (13)H23A—C23—H23C109.5
C7—C12—H12A109.5H23B—C23—H23C109.5
C7—C12—H12B109.5
S1—C1—N2—C5160.74 (11)C6—N1—C1—N2172.91 (12)
S1—C1—N2—C1516.83 (17)C6—N1—C2—C3106.84 (13)
N1—C1—N2—C520.1 (2)C6—C7—C8—C90.4 (2)
N1—C1—N2—C15162.33 (12)C9—C10—C11—C60.4 (2)
N1—C2—C3—C449.58 (15)C9—C10—C11—C14179.36 (13)
N1—C6—C11—C10175.13 (12)C8—C7—C6—N1174.76 (12)
N1—C6—C11—C146.0 (2)C8—C7—C6—C111.7 (2)
C1—N1—C2—C386.27 (15)C8—C9—C10—C111.7 (2)
C1—N1—C6—C796.59 (15)C10—C9—C8—C71.3 (2)
C1—N1—C6—C1186.86 (16)C12—C7—C6—N16.02 (19)
C1—N2—C5—C424.2 (2)C12—C7—C6—C11177.50 (13)
C1—N2—C15—C16101.69 (15)C12—C7—C8—C9178.86 (13)
C1—N2—C15—C2080.59 (16)C13—C9—C8—C7177.75 (14)
C2—N1—C1—S1158.36 (10)C13—C9—C10—C11177.34 (14)
C2—N1—C1—N220.80 (19)C15—N2—C5—C4153.50 (12)
C2—N1—C6—C770.48 (16)C15—C16—C17—C180.6 (2)
C2—N1—C6—C11106.07 (15)C16—C15—C20—C190.7 (2)
C2—C3—C4—C536.75 (16)C16—C15—C20—C23177.42 (13)
N2—C15—C16—C17177.21 (11)C16—C17—C18—C191.3 (2)
N2—C15—C16—C213.45 (19)C16—C17—C18—C22178.76 (14)
N2—C15—C20—C19176.91 (12)C17—C18—C19—C201.0 (2)
N2—C15—C20—C234.93 (19)C18—C19—C20—C150.0 (2)
C3—C4—C5—N279.12 (15)C18—C19—C20—C23178.16 (13)
C5—N2—C15—C1676.22 (15)C20—C15—C16—C170.4 (2)
C5—N2—C15—C20101.49 (14)C20—C15—C16—C21178.91 (12)
C7—C6—C11—C101.3 (2)C21—C16—C17—C18179.97 (13)
C7—C6—C11—C14177.58 (13)C22—C18—C19—C20179.09 (14)
C6—N1—C1—S17.93 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3B···S1i0.993.013.7030 (15)128
C5—H5A···S1i0.992.873.4858 (14)121
Symmetry code: (i) x, y+3/2, z+1/2.
(SDiazMesSe) top
Crystal data top
C23H30N2SeDx = 1.332 Mg m3
Mr = 413.45Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcaCell parameters from 9854 reflections
a = 17.4279 (4) Åθ = 2.2–27.1°
b = 15.2522 (4) ŵ = 1.83 mm1
c = 31.0253 (7) ÅT = 100 K
V = 8247.0 (3) Å3Block, colourless
Z = 160.08 × 0.07 × 0.07 mm
F(000) = 3456
Data collection top
Bruker D8 Venture Photon 2
diffractometer
7294 reflections with I > 2σ(I)
Radiation source: Incoatec IµSRint = 0.072
φ and ω scansθmax = 27.1°, θmin = 2.2°
Absorption correction: multi-scan
SADABS v2016/2 (Bruker AXS Inc., 2017)
h = 2222
Tmin = 0.697, Tmax = 0.746k = 1919
72880 measured reflectionsl = 3936
9109 independent reflections
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.078H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0255P)2 + 7.8329P]
where P = (Fo2 + 2Fc2)/3
9109 reflections(Δ/σ)max = 0.003
481 parametersΔρmax = 0.39 e Å3
0 restraintsΔρmin = 0.33 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
Se10.24756 (2)0.41747 (2)0.61765 (2)0.01788 (6)
N10.27122 (10)0.59242 (11)0.64196 (6)0.0143 (4)
N20.37745 (10)0.52283 (11)0.61141 (6)0.0138 (4)
C10.30350 (12)0.51984 (13)0.62404 (7)0.0128 (4)
C20.29679 (14)0.68578 (14)0.63787 (8)0.0204 (5)
H2A0.3272690.7013510.6636910.024*
H2B0.2508510.7239440.6375120.024*
C30.34430 (14)0.70498 (15)0.59812 (8)0.0221 (5)
H3A0.3439380.7689260.5926540.027*
H3B0.3205470.6757300.5729540.027*
C40.42728 (13)0.67393 (15)0.60253 (9)0.0238 (5)
H4A0.4495080.6646140.5735280.029*
H4B0.4579070.7196340.6172760.029*
C50.43137 (13)0.58965 (15)0.62790 (8)0.0187 (5)
H5A0.4842890.5662400.6265110.022*
H5B0.4193600.6019680.6584970.022*
C60.20033 (12)0.58361 (14)0.66556 (7)0.0145 (4)
C70.13045 (13)0.60225 (14)0.64548 (7)0.0172 (5)
C80.06369 (13)0.59627 (15)0.66997 (8)0.0200 (5)
H80.0157870.6077630.6564970.024*
C90.06462 (14)0.57420 (15)0.71320 (8)0.0212 (5)
C100.13509 (15)0.55836 (16)0.73235 (8)0.0227 (5)
H100.1366420.5437460.7621050.027*
C110.20354 (13)0.56311 (15)0.70954 (7)0.0183 (5)
C120.12753 (15)0.62679 (18)0.59865 (8)0.0270 (6)
H12A0.0760940.6149560.5872890.041*
H12B0.1653400.5921390.5826420.041*
H12C0.1392410.6892970.5954610.041*
C130.00917 (15)0.56505 (17)0.73841 (9)0.0315 (6)
H13A0.0500100.5979530.7239270.047*
H13B0.0018310.5882370.7675780.047*
H13C0.0235120.5030080.7400680.047*
C140.27916 (15)0.54467 (19)0.73116 (8)0.0301 (6)
H14A0.2722700.5451750.7625080.045*
H14B0.3164310.5897970.7229590.045*
H14C0.2980220.4870180.7220850.045*
C150.41106 (12)0.45437 (13)0.58528 (7)0.0137 (4)
C160.40346 (12)0.45655 (14)0.54064 (7)0.0150 (4)
C170.43903 (13)0.39130 (15)0.51629 (8)0.0177 (5)
H170.4343440.3925020.4857850.021*
C180.48113 (12)0.32459 (15)0.53552 (7)0.0172 (4)
C190.48825 (12)0.32494 (14)0.58018 (7)0.0173 (5)
H190.5175630.2801940.5936920.021*
C200.45381 (13)0.38870 (15)0.60559 (7)0.0164 (5)
C210.35540 (14)0.52488 (15)0.51794 (7)0.0204 (5)
H21A0.3045100.5275780.5313070.031*
H21B0.3500990.5091660.4874560.031*
H21C0.3804330.5822110.5203320.031*
C220.51597 (15)0.25184 (16)0.50905 (8)0.0239 (5)
H22A0.5717600.2594610.5078230.036*
H22B0.4948510.2535840.4797890.036*
H22C0.5039320.1951930.5223400.036*
C230.45985 (15)0.38390 (17)0.65411 (8)0.0269 (6)
H23A0.4817640.3272160.6624650.040*
H23B0.4086720.3901030.6668380.040*
H23C0.4930360.4312650.6645090.040*
Se20.36720 (2)0.32364 (2)0.37637 (2)0.01701 (6)
N30.26364 (10)0.19889 (11)0.40670 (6)0.0127 (4)
N40.34705 (10)0.14818 (11)0.35318 (6)0.0132 (4)
C240.32192 (12)0.21407 (13)0.37873 (7)0.0126 (4)
C250.24357 (14)0.10973 (14)0.42179 (7)0.0176 (5)
H25A0.2188010.1141250.4504220.021*
H25B0.2912790.0752040.4252490.021*
C260.19040 (14)0.06168 (15)0.39144 (8)0.0214 (5)
H26A0.1386540.0883250.3926850.026*
H26B0.1860120.0003850.4004520.026*
C270.22096 (14)0.06627 (16)0.34535 (8)0.0219 (5)
H27A0.1998790.0165350.3286100.026*
H27B0.2027840.1211910.3317400.026*
C280.30788 (13)0.06338 (15)0.34332 (8)0.0200 (5)
H28A0.3263240.0185120.3639180.024*
H28B0.3232940.0443430.3140640.024*
C290.22759 (12)0.27116 (13)0.42915 (7)0.0129 (4)
C300.24624 (13)0.28639 (14)0.47206 (7)0.0151 (4)
C310.20980 (13)0.35541 (15)0.49346 (7)0.0175 (5)
H310.2226950.3672620.5226340.021*
C320.15514 (13)0.40709 (14)0.47306 (8)0.0188 (5)
C330.13732 (13)0.38895 (14)0.43025 (7)0.0178 (5)
H330.0997080.4236600.4161050.021*
C340.17286 (12)0.32151 (14)0.40748 (7)0.0146 (4)
C350.30545 (14)0.23231 (16)0.49537 (8)0.0229 (5)
H35A0.2821570.1772850.5051100.034*
H35B0.3245590.2650480.5203380.034*
H35C0.3481550.2194000.4758260.034*
C360.11402 (15)0.47840 (16)0.49765 (9)0.0272 (6)
H36A0.0910770.5199180.4772840.041*
H36B0.1506840.5092970.5161720.041*
H36C0.0736160.4522680.5154730.041*
C370.15406 (13)0.30592 (15)0.36075 (7)0.0193 (5)
H37A0.1139060.3468780.3516130.029*
H37B0.1358890.2455930.3569920.029*
H37C0.2001420.3151250.3432250.029*
C380.41706 (12)0.15949 (13)0.32882 (7)0.0139 (4)
C390.48655 (13)0.13351 (13)0.34659 (7)0.0142 (4)
C400.55311 (13)0.14136 (15)0.32181 (8)0.0187 (5)
H400.6008060.1228100.3334950.022*
C410.55078 (13)0.17592 (15)0.28026 (8)0.0200 (5)
C420.47984 (14)0.20091 (15)0.26341 (7)0.0197 (5)
H420.4778360.2247090.2351320.024*
C430.41222 (13)0.19218 (14)0.28649 (7)0.0162 (5)
C440.49173 (14)0.09976 (15)0.39223 (7)0.0197 (5)
H44A0.4778520.1466950.4123420.029*
H44B0.5443010.0803280.3980970.029*
H44C0.4563970.0503250.3958820.029*
C450.62329 (15)0.18428 (18)0.25400 (9)0.0309 (6)
H45A0.6175480.1516580.2269830.046*
H45B0.6665780.1603620.2703860.046*
H45C0.6328510.2462390.2475950.046*
C460.33635 (14)0.21877 (16)0.26720 (8)0.0234 (5)
H46A0.3447890.2433120.2383940.035*
H46B0.3120210.2629790.2856000.035*
H46C0.3029040.1673020.2650540.035*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Se10.01492 (11)0.01341 (11)0.02531 (12)0.00392 (8)0.00470 (10)0.00215 (9)
N10.0126 (9)0.0128 (9)0.0176 (9)0.0016 (7)0.0028 (7)0.0002 (7)
N20.0118 (9)0.0123 (9)0.0175 (9)0.0008 (7)0.0010 (7)0.0003 (7)
C10.0146 (10)0.0121 (10)0.0117 (10)0.0003 (8)0.0002 (8)0.0030 (8)
C20.0213 (12)0.0113 (11)0.0285 (13)0.0006 (9)0.0037 (10)0.0007 (9)
C30.0227 (12)0.0133 (11)0.0303 (13)0.0027 (9)0.0051 (10)0.0040 (10)
C40.0184 (12)0.0167 (11)0.0362 (14)0.0065 (9)0.0047 (10)0.0020 (11)
C50.0121 (10)0.0195 (11)0.0246 (12)0.0023 (9)0.0030 (9)0.0046 (10)
C60.0137 (11)0.0134 (10)0.0163 (11)0.0005 (8)0.0020 (9)0.0014 (9)
C70.0184 (11)0.0155 (11)0.0176 (11)0.0036 (9)0.0003 (9)0.0005 (9)
C80.0155 (11)0.0192 (12)0.0252 (13)0.0039 (9)0.0009 (10)0.0015 (10)
C90.0203 (12)0.0161 (11)0.0272 (13)0.0007 (9)0.0076 (10)0.0023 (10)
C100.0297 (14)0.0228 (12)0.0155 (11)0.0010 (10)0.0053 (10)0.0025 (9)
C110.0197 (12)0.0165 (11)0.0187 (12)0.0007 (9)0.0005 (9)0.0000 (9)
C120.0229 (13)0.0377 (15)0.0206 (12)0.0080 (11)0.0019 (11)0.0033 (11)
C130.0275 (14)0.0296 (14)0.0375 (16)0.0020 (11)0.0176 (12)0.0018 (12)
C140.0242 (14)0.0461 (17)0.0200 (13)0.0047 (12)0.0040 (11)0.0062 (12)
C150.0102 (10)0.0117 (10)0.0192 (11)0.0005 (8)0.0017 (9)0.0002 (9)
C160.0108 (10)0.0152 (11)0.0189 (11)0.0006 (8)0.0003 (9)0.0054 (9)
C170.0156 (11)0.0188 (11)0.0188 (11)0.0010 (9)0.0020 (9)0.0034 (9)
C180.0133 (10)0.0170 (11)0.0214 (11)0.0001 (9)0.0044 (9)0.0017 (9)
C190.0136 (10)0.0163 (11)0.0220 (11)0.0040 (9)0.0016 (9)0.0050 (9)
C200.0148 (11)0.0187 (11)0.0158 (11)0.0000 (9)0.0017 (9)0.0036 (9)
C210.0233 (12)0.0195 (11)0.0185 (11)0.0068 (10)0.0018 (10)0.0035 (9)
C220.0268 (13)0.0216 (12)0.0234 (13)0.0079 (10)0.0047 (10)0.0015 (10)
C230.0314 (14)0.0307 (14)0.0188 (12)0.0123 (11)0.0028 (11)0.0036 (10)
Se20.01419 (11)0.01075 (10)0.02608 (12)0.00273 (8)0.00550 (9)0.00285 (9)
N30.0130 (9)0.0098 (8)0.0153 (9)0.0005 (7)0.0014 (7)0.0003 (7)
N40.0121 (9)0.0111 (8)0.0166 (9)0.0023 (7)0.0014 (7)0.0033 (7)
C240.0115 (10)0.0119 (10)0.0144 (10)0.0016 (8)0.0034 (9)0.0003 (8)
C250.0238 (12)0.0103 (10)0.0187 (11)0.0030 (9)0.0035 (10)0.0012 (8)
C260.0215 (12)0.0163 (11)0.0263 (13)0.0061 (9)0.0044 (10)0.0021 (10)
C270.0190 (12)0.0231 (12)0.0235 (13)0.0073 (9)0.0016 (10)0.0058 (10)
C280.0206 (12)0.0170 (11)0.0222 (12)0.0026 (9)0.0018 (10)0.0072 (9)
C290.0113 (10)0.0101 (10)0.0172 (11)0.0014 (8)0.0022 (8)0.0015 (8)
C300.0134 (10)0.0155 (11)0.0164 (10)0.0055 (9)0.0020 (9)0.0003 (8)
C310.0174 (11)0.0184 (11)0.0165 (11)0.0064 (9)0.0012 (9)0.0035 (9)
C320.0177 (11)0.0129 (10)0.0257 (12)0.0032 (9)0.0087 (10)0.0024 (9)
C330.0128 (11)0.0170 (11)0.0235 (12)0.0013 (9)0.0055 (9)0.0026 (9)
C340.0115 (10)0.0145 (10)0.0178 (11)0.0030 (8)0.0037 (8)0.0007 (9)
C350.0226 (13)0.0242 (13)0.0219 (12)0.0000 (10)0.0056 (10)0.0003 (10)
C360.0278 (14)0.0213 (12)0.0326 (14)0.0005 (10)0.0114 (11)0.0071 (11)
C370.0159 (11)0.0243 (12)0.0176 (11)0.0037 (9)0.0019 (9)0.0004 (9)
C380.0140 (10)0.0106 (10)0.0172 (11)0.0002 (8)0.0033 (9)0.0047 (8)
C390.0174 (11)0.0109 (10)0.0143 (10)0.0004 (8)0.0004 (9)0.0032 (8)
C400.0165 (11)0.0184 (11)0.0211 (12)0.0024 (9)0.0008 (9)0.0044 (9)
C410.0191 (12)0.0194 (11)0.0214 (12)0.0014 (10)0.0060 (9)0.0071 (10)
C420.0269 (13)0.0191 (11)0.0131 (11)0.0016 (10)0.0026 (10)0.0014 (9)
C430.0192 (11)0.0117 (11)0.0176 (11)0.0002 (8)0.0005 (9)0.0025 (8)
C440.0214 (12)0.0195 (12)0.0181 (11)0.0006 (9)0.0021 (9)0.0008 (9)
C450.0255 (13)0.0373 (15)0.0298 (14)0.0017 (12)0.0127 (11)0.0022 (12)
C460.0196 (12)0.0263 (13)0.0243 (13)0.0023 (10)0.0050 (10)0.0040 (10)
Geometric parameters (Å, º) top
Se1—C11.851 (2)Se2—C241.849 (2)
N1—C11.360 (3)N3—C241.356 (3)
N1—C21.498 (3)N3—C251.480 (3)
N1—C61.442 (3)N3—C291.447 (3)
N2—C11.348 (3)N4—C241.353 (3)
N2—C51.478 (3)N4—C281.494 (3)
N2—C151.446 (3)N4—C381.446 (3)
C2—H2A0.9900C25—H25A0.9900
C2—H2B0.9900C25—H25B0.9900
C2—C31.514 (3)C25—C261.511 (3)
C3—H3A0.9900C26—H26A0.9900
C3—H3B0.9900C26—H26B0.9900
C3—C41.528 (3)C26—C271.528 (3)
C4—H4A0.9900C27—H27A0.9900
C4—H4B0.9900C27—H27B0.9900
C4—C51.509 (3)C27—C281.517 (3)
C5—H5A0.9900C28—H28A0.9900
C5—H5B0.9900C28—H28B0.9900
C6—C71.397 (3)C29—C301.390 (3)
C6—C111.401 (3)C29—C341.397 (3)
C7—C81.393 (3)C30—C311.397 (3)
C7—C121.501 (3)C30—C351.506 (3)
C8—H80.9500C31—H310.9500
C8—C91.383 (3)C31—C321.389 (3)
C9—C101.385 (3)C32—C331.392 (3)
C9—C131.512 (3)C32—C361.509 (3)
C10—H100.9500C33—H330.9500
C10—C111.389 (3)C33—C341.393 (3)
C11—C141.505 (3)C34—C371.505 (3)
C12—H12A0.9800C35—H35A0.9800
C12—H12B0.9800C35—H35B0.9800
C12—H12C0.9800C35—H35C0.9800
C13—H13A0.9800C36—H36A0.9800
C13—H13B0.9800C36—H36B0.9800
C13—H13C0.9800C36—H36C0.9800
C14—H14A0.9800C37—H37A0.9800
C14—H14B0.9800C37—H37B0.9800
C14—H14C0.9800C37—H37C0.9800
C15—C161.392 (3)C38—C391.388 (3)
C15—C201.398 (3)C38—C431.407 (3)
C16—C171.395 (3)C39—C401.397 (3)
C16—C211.511 (3)C39—C441.509 (3)
C17—H170.9500C40—H400.9500
C17—C181.389 (3)C40—C411.393 (3)
C18—C191.391 (3)C41—C421.395 (3)
C18—C221.508 (3)C41—C451.509 (3)
C19—H190.9500C42—H420.9500
C19—C201.388 (3)C42—C431.385 (3)
C20—C231.511 (3)C43—C461.507 (3)
C21—H21A0.9800C44—H44A0.9800
C21—H21B0.9800C44—H44B0.9800
C21—H21C0.9800C44—H44C0.9800
C22—H22A0.9800C45—H45A0.9800
C22—H22B0.9800C45—H45B0.9800
C22—H22C0.9800C45—H45C0.9800
C23—H23A0.9800C46—H46A0.9800
C23—H23B0.9800C46—H46B0.9800
C23—H23C0.9800C46—H46C0.9800
C1—N1—C2128.02 (18)C24—N3—C25122.43 (17)
C1—N1—C6119.07 (17)C24—N3—C29120.21 (17)
C6—N1—C2112.73 (17)C29—N3—C25116.43 (17)
C1—N2—C5122.05 (18)C24—N4—C28127.97 (18)
C1—N2—C15121.73 (18)C24—N4—C38119.40 (17)
C15—N2—C5115.77 (17)C38—N4—C28112.45 (17)
N1—C1—Se1120.80 (15)N3—C24—Se2119.94 (15)
N2—C1—Se1120.06 (15)N4—C24—Se2120.67 (16)
N2—C1—N1119.13 (18)N4—C24—N3119.39 (18)
N1—C2—H2A108.6N3—C25—H25A108.9
N1—C2—H2B108.6N3—C25—H25B108.9
N1—C2—C3114.56 (19)N3—C25—C26113.18 (18)
H2A—C2—H2B107.6H25A—C25—H25B107.8
C3—C2—H2A108.6C26—C25—H25A108.9
C3—C2—H2B108.6C26—C25—H25B108.9
C2—C3—H3A109.1C25—C26—H26A109.6
C2—C3—H3B109.1C25—C26—H26B109.6
C2—C3—C4112.6 (2)C25—C26—C27110.33 (19)
H3A—C3—H3B107.8H26A—C26—H26B108.1
C4—C3—H3A109.1C27—C26—H26A109.6
C4—C3—H3B109.1C27—C26—H26B109.6
C3—C4—H4A109.5C26—C27—H27A109.1
C3—C4—H4B109.5C26—C27—H27B109.1
H4A—C4—H4B108.1H27A—C27—H27B107.8
C5—C4—C3110.82 (19)C28—C27—C26112.7 (2)
C5—C4—H4A109.5C28—C27—H27A109.1
C5—C4—H4B109.5C28—C27—H27B109.1
N2—C5—C4112.15 (19)N4—C28—C27115.00 (19)
N2—C5—H5A109.2N4—C28—H28A108.5
N2—C5—H5B109.2N4—C28—H28B108.5
C4—C5—H5A109.2C27—C28—H28A108.5
C4—C5—H5B109.2C27—C28—H28B108.5
H5A—C5—H5B107.9H28A—C28—H28B107.5
C7—C6—N1120.07 (19)C30—C29—N3119.11 (19)
C7—C6—C11121.0 (2)C30—C29—C34121.9 (2)
C11—C6—N1118.76 (19)C34—C29—N3118.92 (19)
C6—C7—C12120.8 (2)C29—C30—C31118.3 (2)
C8—C7—C6118.1 (2)C29—C30—C35121.9 (2)
C8—C7—C12121.1 (2)C31—C30—C35119.7 (2)
C7—C8—H8118.8C30—C31—H31119.2
C9—C8—C7122.4 (2)C32—C31—C30121.5 (2)
C9—C8—H8118.8C32—C31—H31119.2
C8—C9—C10118.0 (2)C31—C32—C33118.4 (2)
C8—C9—C13121.0 (2)C31—C32—C36120.3 (2)
C10—C9—C13121.1 (2)C33—C32—C36121.3 (2)
C9—C10—H10118.9C32—C33—H33118.9
C9—C10—C11122.3 (2)C32—C33—C34122.1 (2)
C11—C10—H10118.9C34—C33—H33118.9
C6—C11—C14120.7 (2)C29—C34—C37121.69 (19)
C10—C11—C6118.3 (2)C33—C34—C29117.7 (2)
C10—C11—C14121.0 (2)C33—C34—C37120.5 (2)
C7—C12—H12A109.5C30—C35—H35A109.5
C7—C12—H12B109.5C30—C35—H35B109.5
C7—C12—H12C109.5C30—C35—H35C109.5
H12A—C12—H12B109.5H35A—C35—H35B109.5
H12A—C12—H12C109.5H35A—C35—H35C109.5
H12B—C12—H12C109.5H35B—C35—H35C109.5
C9—C13—H13A109.5C32—C36—H36A109.5
C9—C13—H13B109.5C32—C36—H36B109.5
C9—C13—H13C109.5C32—C36—H36C109.5
H13A—C13—H13B109.5H36A—C36—H36B109.5
H13A—C13—H13C109.5H36A—C36—H36C109.5
H13B—C13—H13C109.5H36B—C36—H36C109.5
C11—C14—H14A109.5C34—C37—H37A109.5
C11—C14—H14B109.5C34—C37—H37B109.5
C11—C14—H14C109.5C34—C37—H37C109.5
H14A—C14—H14B109.5H37A—C37—H37B109.5
H14A—C14—H14C109.5H37A—C37—H37C109.5
H14B—C14—H14C109.5H37B—C37—H37C109.5
C16—C15—N2120.15 (19)C39—C38—N4119.64 (19)
C16—C15—C20121.1 (2)C39—C38—C43121.6 (2)
C20—C15—N2118.72 (19)C43—C38—N4118.66 (19)
C15—C16—C17118.7 (2)C38—C39—C40118.8 (2)
C15—C16—C21122.2 (2)C38—C39—C44121.5 (2)
C17—C16—C21119.1 (2)C40—C39—C44119.7 (2)
C16—C17—H17119.2C39—C40—H40119.4
C18—C17—C16121.6 (2)C41—C40—C39121.2 (2)
C18—C17—H17119.2C41—C40—H40119.4
C17—C18—C19118.2 (2)C40—C41—C42118.4 (2)
C17—C18—C22121.2 (2)C40—C41—C45120.5 (2)
C19—C18—C22120.6 (2)C42—C41—C45121.1 (2)
C18—C19—H19119.0C41—C42—H42118.9
C20—C19—C18122.0 (2)C43—C42—C41122.3 (2)
C20—C19—H19119.0C43—C42—H42118.9
C15—C20—C23121.4 (2)C38—C43—C46121.2 (2)
C19—C20—C15118.4 (2)C42—C43—C38117.7 (2)
C19—C20—C23120.1 (2)C42—C43—C46121.0 (2)
C16—C21—H21A109.5C39—C44—H44A109.5
C16—C21—H21B109.5C39—C44—H44B109.5
C16—C21—H21C109.5C39—C44—H44C109.5
H21A—C21—H21B109.5H44A—C44—H44B109.5
H21A—C21—H21C109.5H44A—C44—H44C109.5
H21B—C21—H21C109.5H44B—C44—H44C109.5
C18—C22—H22A109.5C41—C45—H45A109.5
C18—C22—H22B109.5C41—C45—H45B109.5
C18—C22—H22C109.5C41—C45—H45C109.5
H22A—C22—H22B109.5H45A—C45—H45B109.5
H22A—C22—H22C109.5H45A—C45—H45C109.5
H22B—C22—H22C109.5H45B—C45—H45C109.5
C20—C23—H23A109.5C43—C46—H46A109.5
C20—C23—H23B109.5C43—C46—H46B109.5
C20—C23—H23C109.5C43—C46—H46C109.5
H23A—C23—H23B109.5H46A—C46—H46B109.5
H23A—C23—H23C109.5H46A—C46—H46C109.5
H23B—C23—H23C109.5H46B—C46—H46C109.5
N1—C2—C3—C477.6 (3)N3—C25—C26—C2749.7 (3)
N1—C6—C7—C8177.5 (2)N3—C29—C30—C31178.80 (19)
N1—C6—C7—C123.4 (3)N3—C29—C30—C352.7 (3)
N1—C6—C11—C10177.4 (2)N3—C29—C34—C33178.04 (18)
N1—C6—C11—C144.0 (3)N3—C29—C34—C373.7 (3)
N2—C15—C16—C17177.61 (19)N4—C38—C39—C40177.18 (19)
N2—C15—C16—C215.0 (3)N4—C38—C39—C444.6 (3)
N2—C15—C20—C19177.70 (19)N4—C38—C43—C42178.76 (19)
N2—C15—C20—C235.1 (3)N4—C38—C43—C462.6 (3)
C1—N1—C2—C323.4 (3)C24—N3—C25—C2685.0 (3)
C1—N1—C6—C797.6 (2)C24—N3—C29—C30102.6 (2)
C1—N1—C6—C1187.5 (3)C24—N3—C29—C3479.8 (3)
C1—N2—C5—C485.3 (3)C24—N4—C28—C2728.3 (3)
C1—N2—C15—C1684.9 (3)C24—N4—C38—C3991.4 (2)
C1—N2—C15—C2097.8 (2)C24—N4—C38—C4392.1 (2)
C2—N1—C1—Se1159.59 (18)C25—N3—C24—Se2157.52 (16)
C2—N1—C1—N221.3 (3)C25—N3—C24—N421.6 (3)
C2—N1—C6—C778.0 (3)C25—N3—C29—C3066.6 (3)
C2—N1—C6—C1196.9 (2)C25—N3—C29—C34111.0 (2)
C2—C3—C4—C535.7 (3)C25—C26—C27—C2835.3 (3)
C3—C4—C5—N250.3 (3)C26—C27—C28—N479.3 (3)
C5—N2—C1—Se1159.66 (16)C28—N4—C24—Se2165.05 (17)
C5—N2—C1—N119.5 (3)C28—N4—C24—N315.9 (3)
C5—N2—C15—C16102.6 (2)C28—N4—C38—C3993.1 (2)
C5—N2—C15—C2074.6 (2)C28—N4—C38—C4383.3 (2)
C6—N1—C1—Se115.3 (3)C29—N3—C24—Se211.0 (3)
C6—N1—C1—N2163.81 (19)C29—N3—C24—N4169.90 (19)
C6—N1—C2—C3151.8 (2)C29—N3—C25—C26106.1 (2)
C6—C7—C8—C91.1 (3)C29—C30—C31—C321.2 (3)
C7—C6—C11—C102.5 (3)C30—C29—C34—C330.5 (3)
C7—C6—C11—C14178.9 (2)C30—C29—C34—C37178.7 (2)
C7—C8—C9—C100.5 (3)C30—C31—C32—C330.3 (3)
C7—C8—C9—C13177.7 (2)C30—C31—C32—C36177.1 (2)
C8—C9—C10—C110.7 (4)C31—C32—C33—C340.5 (3)
C9—C10—C11—C60.8 (4)C32—C33—C34—C290.4 (3)
C9—C10—C11—C14179.4 (2)C32—C33—C34—C37177.8 (2)
C11—C6—C7—C82.7 (3)C34—C29—C30—C311.3 (3)
C11—C6—C7—C12178.2 (2)C34—C29—C30—C35179.8 (2)
C12—C7—C8—C9179.7 (2)C35—C30—C31—C32179.7 (2)
C13—C9—C10—C11177.6 (2)C36—C32—C33—C34177.8 (2)
C15—N2—C1—Se112.3 (3)C38—N4—C24—Se29.6 (3)
C15—N2—C1—N1168.57 (19)C38—N4—C24—N3169.51 (19)
C15—N2—C5—C4102.3 (2)C38—N4—C28—C27146.7 (2)
C15—C16—C17—C180.3 (3)C38—C39—C40—C411.1 (3)
C16—C15—C20—C190.5 (3)C39—C38—C43—C422.4 (3)
C16—C15—C20—C23177.7 (2)C39—C38—C43—C46178.9 (2)
C16—C17—C18—C191.0 (3)C39—C40—C41—C421.4 (3)
C16—C17—C18—C22176.9 (2)C39—C40—C41—C45179.7 (2)
C17—C18—C19—C201.0 (3)C40—C41—C42—C430.2 (3)
C18—C19—C20—C150.2 (3)C41—C42—C43—C382.1 (3)
C18—C19—C20—C23177.0 (2)C41—C42—C43—C46179.3 (2)
C20—C15—C16—C170.4 (3)C43—C38—C39—C400.9 (3)
C20—C15—C16—C21177.9 (2)C43—C38—C39—C44179.1 (2)
C21—C16—C17—C18177.2 (2)C44—C39—C40—C41177.1 (2)
C22—C18—C19—C20176.9 (2)C45—C41—C42—C43178.6 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2B···Se1i0.993.023.671 (2)125
C3—H3A···Se1i0.992.883.665 (2)137
C4—H4B···Se2ii0.993.123.641 (2)114
C5—H5A···Se2ii0.993.093.754 (2)126
C26—H26B···Se2iii0.992.943.796 (2)146
Symmetry codes: (i) x+1/2, y+1/2, z; (ii) x+1, y+1, z+1; (iii) x+1/2, y1/2, z.
(SDiazMesS_MeCN) top
Crystal data top
C23H30N2S·C2H3NF(000) = 880
Mr = 407.60Dx = 1.200 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 13.0884 (6) ÅCell parameters from 9891 reflections
b = 12.9760 (5) Åθ = 2.3–27.5°
c = 14.4293 (7) ŵ = 0.16 mm1
β = 113.028 (2)°T = 100 K
V = 2255.32 (18) Å3Plank, colourless
Z = 40.26 × 0.17 × 0.10 mm
Data collection top
Bruker D8 Venture Photon 2
diffractometer
4419 reflections with I > 2σ(I)
Radiation source: Incoatec IµSRint = 0.046
φ and ω scansθmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan
SADABS v2016/2 (Bruker AXS Inc., 2017)
h = 1617
Tmin = 0.711, Tmax = 0.746k = 1616
34671 measured reflectionsl = 1818
5148 independent reflections
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0294P)2 + 1.5344P]
where P = (Fo2 + 2Fc2)/3
5148 reflections(Δ/σ)max = 0.001
288 parametersΔρmax = 0.28 e Å3
36 restraintsΔρmin = 0.21 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)
S10.43804 (3)0.35053 (3)0.58591 (3)0.02002 (9)
N10.28488 (9)0.23910 (8)0.61966 (8)0.0165 (2)
N20.46730 (9)0.20752 (8)0.72720 (9)0.0187 (2)
N30.09785 (14)0.67080 (12)0.36918 (13)0.0476 (4)
C10.39454 (10)0.26151 (10)0.64704 (10)0.0166 (3)
C20.23875 (11)0.20489 (10)0.69367 (10)0.0197 (3)
H2A0.1586300.2218130.6666600.024*
H2B0.2751530.2448550.7565070.024*
C30.25226 (12)0.09117 (11)0.71954 (12)0.0244 (3)0.853 (4)
H3A0.2285970.0501710.6567540.029*0.853 (4)
H3B0.2041170.0722630.7554000.029*0.853 (4)
C40.37427 (14)0.06553 (13)0.78649 (15)0.0222 (4)0.853 (4)
H4A0.3962980.1033390.8509900.027*0.853 (4)
H4B0.3810610.0091560.8017390.027*0.853 (4)
C50.45187 (13)0.09440 (12)0.73532 (14)0.0184 (4)0.853 (4)
H5A0.5253120.0627960.7732390.022*0.853 (4)
H5B0.4226430.0644500.6667580.022*0.853 (4)
C3B0.25226 (12)0.09117 (11)0.71954 (12)0.0244 (3)0.147 (4)
H3BA0.2468000.0807090.7854090.029*0.147 (4)
H3BB0.1906720.0526800.6682540.029*0.147 (4)
C4B0.3582 (8)0.0489 (7)0.7244 (9)0.023 (2)0.147 (4)
H4BA0.3596140.0463350.6563330.027*0.147 (4)
H4BB0.3692090.0217650.7525370.027*0.147 (4)
C5B0.4460 (8)0.1189 (8)0.7908 (8)0.020 (2)0.147 (4)
H5BA0.5154480.0795550.8253700.024*0.147 (4)
H5BB0.4228050.1485300.8427080.024*0.147 (4)
C60.20570 (10)0.28179 (10)0.52689 (10)0.0163 (3)
C70.15783 (10)0.37797 (10)0.52853 (10)0.0184 (3)
C80.08166 (10)0.41758 (10)0.43835 (10)0.0192 (3)
H80.0482920.4825450.4385700.023*
C90.05303 (10)0.36447 (10)0.34774 (10)0.0187 (3)
C100.10009 (11)0.26778 (10)0.34924 (10)0.0185 (3)
H100.0792100.2297090.2883640.022*
C110.17719 (10)0.22557 (10)0.43810 (10)0.0173 (3)
C120.18995 (12)0.43966 (11)0.62429 (11)0.0246 (3)
H12A0.1675020.5116290.6077620.037*
H12B0.2705510.4361910.6615940.037*
H12C0.1526800.4112790.6657790.037*
C130.02441 (11)0.41249 (11)0.24993 (11)0.0234 (3)
H13A0.0936420.4328480.2559750.035*
H13B0.0406980.3623490.1952130.035*
H13C0.0109500.4733900.2352270.035*
C140.22854 (12)0.12205 (11)0.43677 (11)0.0229 (3)
H14A0.3093810.1293080.4615150.034*
H14B0.1999120.0953430.3677470.034*
H14C0.2097420.0741040.4801780.034*
C150.57768 (11)0.24817 (10)0.78090 (10)0.0179 (3)
C160.59395 (11)0.31750 (10)0.85958 (10)0.0188 (3)
C170.70119 (11)0.35298 (10)0.91484 (10)0.0203 (3)
H170.7130240.3999660.9685600.024*
C180.79137 (11)0.32167 (11)0.89370 (10)0.0210 (3)
C190.77190 (11)0.25361 (11)0.81392 (10)0.0207 (3)
H190.8326190.2322590.7980860.025*
C200.66612 (11)0.21580 (10)0.75651 (10)0.0195 (3)
C210.49809 (11)0.35392 (11)0.88439 (11)0.0228 (3)
H21A0.5236440.4082640.9355160.034*
H21B0.4690450.2960150.9103280.034*
H21C0.4393270.3811150.8234370.034*
C220.90777 (12)0.35963 (12)0.95412 (12)0.0281 (3)
H22A0.9052970.4142021.0001460.042*
H22B0.9401770.3869070.9083570.042*
H22C0.9533020.3023820.9930330.042*
C230.64884 (12)0.14485 (11)0.66898 (11)0.0257 (3)
H23A0.7088500.1548470.6453020.039*
H23B0.5774390.1603750.6142210.039*
H23C0.6489800.0731930.6904720.039*
C240.18720 (14)0.64241 (12)0.41048 (12)0.0315 (4)
C250.29974 (13)0.60517 (12)0.46426 (13)0.0313 (3)
H25A0.3291790.6328880.5329060.047*
H25B0.3466120.6277850.4292370.047*
H25C0.2993350.5297080.4669050.047*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.01496 (16)0.02198 (17)0.02167 (17)0.00078 (12)0.00560 (13)0.00425 (13)
N10.0129 (5)0.0196 (5)0.0156 (5)0.0005 (4)0.0040 (4)0.0018 (4)
N20.0138 (5)0.0164 (5)0.0214 (6)0.0005 (4)0.0020 (4)0.0038 (4)
N30.0424 (9)0.0371 (8)0.0448 (9)0.0020 (7)0.0029 (7)0.0127 (7)
C10.0146 (6)0.0160 (6)0.0178 (6)0.0017 (5)0.0048 (5)0.0015 (5)
C20.0175 (6)0.0239 (7)0.0188 (6)0.0016 (5)0.0082 (5)0.0017 (5)
C30.0242 (7)0.0228 (7)0.0299 (8)0.0002 (6)0.0147 (6)0.0050 (6)
C40.0241 (9)0.0197 (8)0.0240 (10)0.0017 (6)0.0109 (8)0.0051 (7)
C50.0173 (7)0.0152 (7)0.0217 (9)0.0016 (6)0.0065 (6)0.0018 (6)
C3B0.0242 (7)0.0228 (7)0.0299 (8)0.0002 (6)0.0147 (6)0.0050 (6)
C4B0.022 (4)0.018 (4)0.023 (4)0.001 (3)0.004 (3)0.007 (3)
C5B0.021 (4)0.022 (4)0.020 (4)0.008 (3)0.009 (3)0.009 (3)
C60.0109 (5)0.0206 (6)0.0156 (6)0.0010 (5)0.0035 (5)0.0020 (5)
C70.0134 (6)0.0222 (6)0.0192 (6)0.0006 (5)0.0058 (5)0.0004 (5)
C80.0140 (6)0.0204 (6)0.0229 (7)0.0024 (5)0.0069 (5)0.0021 (5)
C90.0125 (6)0.0248 (7)0.0186 (6)0.0009 (5)0.0057 (5)0.0041 (5)
C100.0144 (6)0.0240 (6)0.0166 (6)0.0029 (5)0.0053 (5)0.0008 (5)
C110.0135 (6)0.0189 (6)0.0193 (6)0.0018 (5)0.0062 (5)0.0003 (5)
C120.0242 (7)0.0247 (7)0.0216 (7)0.0069 (6)0.0052 (6)0.0032 (6)
C130.0184 (6)0.0288 (7)0.0203 (7)0.0027 (5)0.0044 (5)0.0053 (6)
C140.0245 (7)0.0209 (7)0.0216 (7)0.0018 (5)0.0073 (6)0.0018 (5)
C150.0136 (6)0.0190 (6)0.0176 (6)0.0006 (5)0.0022 (5)0.0035 (5)
C160.0175 (6)0.0197 (6)0.0184 (6)0.0016 (5)0.0061 (5)0.0040 (5)
C170.0201 (6)0.0217 (6)0.0179 (6)0.0008 (5)0.0062 (5)0.0017 (5)
C180.0160 (6)0.0238 (7)0.0204 (7)0.0012 (5)0.0040 (5)0.0010 (5)
C190.0148 (6)0.0246 (7)0.0216 (7)0.0023 (5)0.0058 (5)0.0001 (5)
C200.0181 (6)0.0193 (6)0.0185 (6)0.0023 (5)0.0043 (5)0.0013 (5)
C210.0190 (6)0.0281 (7)0.0225 (7)0.0026 (5)0.0095 (6)0.0013 (6)
C220.0175 (7)0.0341 (8)0.0290 (8)0.0041 (6)0.0053 (6)0.0069 (6)
C230.0208 (7)0.0280 (7)0.0245 (7)0.0029 (6)0.0046 (6)0.0061 (6)
C240.0391 (9)0.0238 (7)0.0262 (8)0.0071 (6)0.0069 (7)0.0029 (6)
C250.0302 (8)0.0290 (8)0.0348 (9)0.0028 (6)0.0128 (7)0.0034 (7)
Geometric parameters (Å, º) top
S1—C11.6821 (14)C10—H100.9500
N1—C11.3627 (16)C10—C111.3964 (18)
N1—C21.4854 (17)C11—C141.5055 (18)
N1—C61.4448 (16)C12—H12A0.9800
N2—C11.3688 (16)C12—H12B0.9800
N2—C51.4925 (18)C12—H12C0.9800
N2—C5B1.563 (9)C13—H13A0.9800
N2—C151.4456 (16)C13—H13B0.9800
N3—C241.146 (2)C13—H13C0.9800
C2—H2A0.9900C14—H14A0.9800
C2—H2B0.9900C14—H14B0.9800
C2—C31.5154 (19)C14—H14C0.9800
C2—C3B1.5154 (19)C15—C161.3980 (19)
C3—H3A0.9900C15—C201.3997 (19)
C3—H3B0.9900C16—C171.3936 (19)
C3—C41.545 (2)C16—C211.5090 (19)
C4—H4A0.9900C17—H170.9500
C4—H4B0.9900C17—C181.390 (2)
C4—C51.518 (2)C18—C191.393 (2)
C5—H5A0.9900C18—C221.5114 (19)
C5—H5B0.9900C19—H190.9500
C3B—H3BA0.9900C19—C201.3952 (19)
C3B—H3BB0.9900C20—C231.5068 (19)
C3B—C4B1.467 (10)C21—H21A0.9800
C4B—H4BA0.9900C21—H21B0.9800
C4B—H4BB0.9900C21—H21C0.9800
C4B—C5B1.485 (15)C22—H22A0.9800
C5B—H5BA0.9900C22—H22B0.9800
C5B—H5BB0.9900C22—H22C0.9800
C6—C71.4009 (18)C23—H23A0.9800
C6—C111.3924 (18)C23—H23B0.9800
C7—C81.3915 (18)C23—H23C0.9800
C7—C121.5074 (19)C24—C251.453 (2)
C8—H80.9500C25—H25A0.9800
C8—C91.3934 (19)C25—H25B0.9800
C9—C101.3940 (19)C25—H25C0.9800
C9—C131.5128 (18)
C1—N1—C2122.24 (11)C9—C10—C11121.56 (12)
C1—N1—C6118.64 (11)C11—C10—H10119.2
C6—N1—C2115.77 (10)C6—C11—C10118.46 (12)
C1—N2—C5119.93 (11)C6—C11—C14121.26 (12)
C1—N2—C5B130.4 (4)C10—C11—C14120.27 (12)
C1—N2—C15119.03 (11)C7—C12—H12A109.5
C15—N2—C5117.02 (11)C7—C12—H12B109.5
C15—N2—C5B108.9 (4)C7—C12—H12C109.5
N1—C1—S1121.91 (10)H12A—C12—H12B109.5
N1—C1—N2116.20 (11)H12A—C12—H12C109.5
N2—C1—S1121.89 (10)H12B—C12—H12C109.5
N1—C2—H2A108.5C9—C13—H13A109.5
N1—C2—H2B108.5C9—C13—H13B109.5
N1—C2—C3115.28 (11)C9—C13—H13C109.5
N1—C2—C3B115.28 (11)H13A—C13—H13B109.5
H2A—C2—H2B107.5H13A—C13—H13C109.5
C3—C2—H2A108.5H13B—C13—H13C109.5
C3—C2—H2B108.5C11—C14—H14A109.5
C2—C3—H3A109.5C11—C14—H14B109.5
C2—C3—H3B109.5C11—C14—H14C109.5
C2—C3—C4110.87 (12)H14A—C14—H14B109.5
H3A—C3—H3B108.1H14A—C14—H14C109.5
C4—C3—H3A109.5H14B—C14—H14C109.5
C4—C3—H3B109.5C16—C15—N2118.23 (12)
C3—C4—H4A109.3C16—C15—C20121.26 (12)
C3—C4—H4B109.3C20—C15—N2120.47 (12)
H4A—C4—H4B108.0C15—C16—C21121.16 (12)
C5—C4—C3111.55 (14)C17—C16—C15118.47 (12)
C5—C4—H4A109.3C17—C16—C21120.37 (13)
C5—C4—H4B109.3C16—C17—H17119.0
N2—C5—C4114.70 (14)C18—C17—C16121.96 (13)
N2—C5—H5A108.6C18—C17—H17119.0
N2—C5—H5B108.6C17—C18—C19118.04 (12)
C4—C5—H5A108.6C17—C18—C22121.93 (13)
C4—C5—H5B108.6C19—C18—C22120.03 (13)
H5A—C5—H5B107.6C18—C19—H19118.9
C2—C3B—H3BA108.9C18—C19—C20122.13 (13)
C2—C3B—H3BB108.9C20—C19—H19118.9
H3BA—C3B—H3BB107.8C15—C20—C23121.76 (12)
C4B—C3B—C2113.2 (4)C19—C20—C15118.13 (13)
C4B—C3B—H3BA108.9C19—C20—C23120.08 (12)
C4B—C3B—H3BB108.9C16—C21—H21A109.5
C3B—C4B—H4BA110.5C16—C21—H21B109.5
C3B—C4B—H4BB110.5C16—C21—H21C109.5
C3B—C4B—C5B106.3 (9)H21A—C21—H21B109.5
H4BA—C4B—H4BB108.7H21A—C21—H21C109.5
C5B—C4B—H4BA110.5H21B—C21—H21C109.5
C5B—C4B—H4BB110.5C18—C22—H22A109.5
N2—C5B—H5BA109.7C18—C22—H22B109.5
N2—C5B—H5BB109.7C18—C22—H22C109.5
C4B—C5B—N2110.0 (8)H22A—C22—H22B109.5
C4B—C5B—H5BA109.7H22A—C22—H22C109.5
C4B—C5B—H5BB109.7H22B—C22—H22C109.5
H5BA—C5B—H5BB108.2C20—C23—H23A109.5
C7—C6—N1119.30 (12)C20—C23—H23B109.5
C11—C6—N1119.25 (11)C20—C23—H23C109.5
C11—C6—C7121.45 (12)H23A—C23—H23B109.5
C6—C7—C12121.49 (12)H23A—C23—H23C109.5
C8—C7—C6118.34 (12)H23B—C23—H23C109.5
C8—C7—C12120.13 (12)N3—C24—C25178.80 (19)
C7—C8—H8119.1C24—C25—H25A109.5
C7—C8—C9121.74 (12)C24—C25—H25B109.5
C9—C8—H8119.1C24—C25—H25C109.5
C8—C9—C10118.40 (12)H25A—C25—H25B109.5
C8—C9—C13120.52 (12)H25A—C25—H25C109.5
C10—C9—C13121.06 (13)H25B—C25—H25C109.5
C9—C10—H10119.2
N1—C2—C3—C472.82 (16)C5B—N2—C15—C2098.3 (5)
N1—C2—C3B—C4B37.0 (5)C6—N1—C1—S19.29 (17)
N1—C6—C7—C8179.91 (11)C6—N1—C1—N2170.76 (11)
N1—C6—C7—C122.12 (19)C6—N1—C2—C3118.47 (13)
N1—C6—C11—C10179.67 (11)C6—N1—C2—C3B118.47 (13)
N1—C6—C11—C140.92 (18)C6—C7—C8—C90.4 (2)
N2—C15—C16—C17176.86 (12)C7—C6—C11—C100.82 (19)
N2—C15—C16—C213.40 (19)C7—C6—C11—C14179.77 (12)
N2—C15—C20—C19176.92 (12)C7—C8—C9—C102.0 (2)
N2—C15—C20—C235.0 (2)C7—C8—C9—C13176.07 (12)
C1—N1—C2—C382.51 (16)C8—C9—C10—C112.25 (19)
C1—N1—C2—C3B82.51 (16)C9—C10—C11—C60.87 (19)
C1—N1—C6—C789.84 (15)C9—C10—C11—C14178.55 (12)
C1—N1—C6—C1191.29 (15)C11—C6—C7—C81.07 (19)
C1—N2—C5—C486.51 (18)C11—C6—C7—C12179.03 (12)
C1—N2—C5B—C4B38.3 (10)C12—C7—C8—C9177.61 (12)
C1—N2—C15—C1687.17 (16)C13—C9—C10—C11175.81 (12)
C1—N2—C15—C2094.99 (15)C15—N2—C1—S119.92 (17)
C2—N1—C1—S1149.15 (10)C15—N2—C1—N1160.03 (12)
C2—N1—C1—N230.80 (17)C15—N2—C5—C4116.25 (15)
C2—N1—C6—C769.98 (15)C15—N2—C5B—C4B156.9 (6)
C2—N1—C6—C11108.90 (13)C15—C16—C17—C180.2 (2)
C2—C3—C4—C558.41 (18)C16—C15—C20—C190.9 (2)
C2—C3B—C4B—C5B50.5 (8)C16—C15—C20—C23177.21 (13)
C3—C4—C5—N270.95 (19)C16—C17—C18—C190.7 (2)
C5—N2—C1—S1136.86 (12)C16—C17—C18—C22179.58 (13)
C5—N2—C1—N143.19 (18)C17—C18—C19—C200.8 (2)
C5—N2—C15—C16115.39 (15)C18—C19—C20—C150.0 (2)
C5—N2—C15—C2062.46 (18)C18—C19—C20—C23178.14 (13)
C3B—C4B—C5B—N288.9 (9)C20—C15—C16—C171.0 (2)
C5B—N2—C1—S1176.6 (6)C20—C15—C16—C21178.77 (12)
C5B—N2—C1—N13.4 (6)C21—C16—C17—C18179.56 (13)
C5B—N2—C15—C1679.6 (5)C22—C18—C19—C20179.46 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4B···S1i0.992.923.6972 (17)136
C25—H25B···S1ii0.982.923.8180 (17)152
Symmetry codes: (i) x+1, y1/2, z+3/2; (ii) x+1, y+1, z+1.
(SDiazMesSe_MeCN) top
Crystal data top
C23H30N2Se·C2H3NF(000) = 952
Mr = 454.50Dx = 1.319 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 13.1365 (3) ÅCell parameters from 9757 reflections
b = 13.3024 (2) Åθ = 2.2–27.5°
c = 14.2478 (3) ŵ = 1.66 mm1
β = 113.1557 (7)°T = 100 K
V = 2289.18 (8) Å3Block, yellow
Z = 40.23 × 0.19 × 0.10 mm
Data collection top
Bruker D8 Venture Photon 2
diffractometer
4637 reflections with I > 2σ(I)
Radiation source: Incoatec IµSRint = 0.046
φ and ω scansθmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan
SADABS v2016/2 (Bruker AXS Inc., 2017)
h = 1717
Tmin = 0.683, Tmax = 0.746k = 1717
40871 measured reflectionsl = 1818
5251 independent reflections
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.026Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.061H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0125P)2 + 1.9573P]
where P = (Fo2 + 2Fc2)/3
5251 reflections(Δ/σ)max = 0.003
288 parametersΔρmax = 0.36 e Å3
36 restraintsΔρmin = 0.33 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)
Se10.44339 (2)0.35467 (2)0.58253 (2)0.01973 (5)
N10.28687 (10)0.24512 (10)0.62785 (9)0.0161 (3)
N20.46935 (11)0.21612 (10)0.73881 (11)0.0213 (3)
C10.39611 (13)0.26432 (11)0.65558 (12)0.0172 (3)
C20.24099 (13)0.20892 (12)0.70159 (12)0.0188 (3)
H2A0.1620630.2285860.6767980.023*
H2B0.2805510.2427820.7679360.023*
C30.24979 (14)0.09602 (13)0.71822 (14)0.0249 (4)0.367 (5)
H3A0.2291120.0603440.6523200.030*0.367 (5)
H3B0.2001940.0734420.7513830.030*0.367 (5)
C3B0.24979 (14)0.09602 (13)0.71822 (14)0.0249 (4)0.633 (5)
H3BA0.2383420.0794860.7811180.030*0.633 (5)
H3BB0.1909780.0622710.6601680.030*0.633 (5)
C40.3775 (4)0.0740 (3)0.7910 (4)0.0212 (11)0.367 (5)
H4A0.3977750.1131690.8549070.025*0.367 (5)
H4B0.3865080.0017830.8091870.025*0.367 (5)
C4B0.3613 (2)0.0575 (2)0.7277 (2)0.0204 (7)0.633 (5)
H4BA0.3637370.0540380.6591730.024*0.633 (5)
H4BB0.3728060.0112300.7567320.024*0.633 (5)
C50.4536 (4)0.1018 (3)0.7391 (4)0.0185 (11)0.367 (5)
H5A0.4223540.0767770.6678980.022*0.367 (5)
H5B0.5264560.0691350.7749580.022*0.367 (5)
C5B0.4524 (2)0.1260 (2)0.7958 (2)0.0193 (7)0.633 (5)
H5BA0.4336280.1495390.8529440.023*0.633 (5)
H5BB0.5223810.0875220.8250800.023*0.633 (5)
C60.20736 (12)0.28483 (12)0.53284 (11)0.0160 (3)
C70.15910 (12)0.37867 (12)0.53314 (12)0.0175 (3)
C80.08250 (12)0.41582 (12)0.44127 (12)0.0187 (3)
H80.0491800.4793780.4404620.022*
C90.05335 (12)0.36221 (12)0.35034 (12)0.0184 (3)
C100.10020 (12)0.26774 (12)0.35358 (12)0.0181 (3)
H100.0787400.2293230.2926210.022*
C110.17782 (12)0.22801 (12)0.44398 (12)0.0172 (3)
C120.19143 (14)0.44013 (13)0.62932 (12)0.0237 (3)
H12A0.1693880.5102620.6116030.036*
H12B0.2717970.4365670.6673110.036*
H12C0.1541380.4135510.6716180.036*
C130.02406 (13)0.40737 (14)0.25048 (12)0.0234 (3)
H13A0.0886890.4359530.2589420.035*
H13B0.0482860.3549990.1978910.035*
H13C0.0145610.4604570.2298060.035*
C140.22918 (14)0.12664 (12)0.44389 (13)0.0227 (3)
H14A0.3098920.1335080.4702150.034*
H14B0.2016740.1003650.3740360.034*
H14C0.2093530.0801690.4873560.034*
C150.58038 (12)0.25532 (12)0.78975 (12)0.0189 (3)
C160.59968 (13)0.32537 (12)0.86766 (12)0.0202 (3)
C170.70831 (14)0.35784 (13)0.92191 (12)0.0221 (3)
H170.7227170.4046350.9759980.027*
C180.79588 (13)0.32364 (13)0.89901 (13)0.0222 (3)
C190.77327 (13)0.25401 (13)0.82044 (12)0.0216 (3)
H190.8323400.2301250.8038890.026*
C200.66649 (13)0.21832 (12)0.76533 (12)0.0211 (3)
C210.50612 (14)0.36652 (14)0.89236 (13)0.0256 (4)
H21A0.5343100.4196610.9437890.038*
H21B0.4744260.3123960.9190200.038*
H21C0.4488370.3942340.8303240.038*
C220.91285 (14)0.36019 (15)0.95683 (14)0.0300 (4)
H22A0.9126690.4144341.0033060.045*
H22B0.9431190.3853240.9084630.045*
H22C0.9586750.3045150.9962610.045*
C230.64518 (15)0.14426 (14)0.67956 (14)0.0312 (4)
H23A0.7106000.1401190.6627760.047*
H23B0.5814160.1666030.6193800.047*
H23C0.6296770.0779050.7007870.047*
N30.07928 (16)0.66649 (14)0.36865 (15)0.0471 (5)
C240.17011 (17)0.64243 (14)0.40537 (14)0.0313 (4)
C250.28509 (16)0.61080 (15)0.45398 (16)0.0335 (4)
H25A0.3207310.6458780.5193060.050*
H25B0.3237670.6271220.4094890.050*
H25C0.2882560.5381000.4659090.050*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Se10.01439 (8)0.02322 (9)0.02095 (8)0.00069 (6)0.00629 (6)0.00366 (6)
N10.0141 (6)0.0181 (6)0.0157 (6)0.0007 (5)0.0055 (5)0.0013 (5)
N20.0135 (6)0.0189 (7)0.0270 (7)0.0004 (5)0.0031 (5)0.0073 (6)
C10.0158 (7)0.0155 (7)0.0190 (7)0.0007 (6)0.0054 (6)0.0023 (6)
C20.0172 (7)0.0222 (8)0.0184 (7)0.0017 (6)0.0087 (6)0.0013 (6)
C30.0246 (8)0.0247 (9)0.0299 (9)0.0001 (7)0.0154 (7)0.0061 (7)
C3B0.0246 (8)0.0247 (9)0.0299 (9)0.0001 (7)0.0154 (7)0.0061 (7)
C40.021 (2)0.020 (2)0.024 (3)0.0033 (17)0.0091 (18)0.0034 (18)
C4B0.0218 (13)0.0167 (12)0.0204 (15)0.0024 (10)0.0059 (11)0.0001 (10)
C50.018 (2)0.015 (2)0.020 (2)0.0002 (16)0.0058 (17)0.0003 (17)
C5B0.0209 (12)0.0165 (13)0.0176 (14)0.0005 (10)0.0046 (10)0.0041 (10)
C60.0113 (7)0.0198 (7)0.0162 (7)0.0001 (6)0.0049 (6)0.0022 (6)
C70.0135 (7)0.0196 (8)0.0194 (7)0.0008 (6)0.0064 (6)0.0007 (6)
C80.0140 (7)0.0208 (8)0.0219 (8)0.0022 (6)0.0075 (6)0.0020 (6)
C90.0129 (7)0.0247 (8)0.0178 (7)0.0008 (6)0.0063 (6)0.0026 (6)
C100.0154 (7)0.0231 (8)0.0161 (7)0.0039 (6)0.0064 (6)0.0014 (6)
C110.0140 (7)0.0192 (7)0.0195 (7)0.0014 (6)0.0080 (6)0.0001 (6)
C120.0212 (8)0.0241 (8)0.0220 (8)0.0059 (7)0.0043 (7)0.0035 (7)
C130.0179 (8)0.0305 (9)0.0199 (8)0.0021 (7)0.0055 (6)0.0034 (7)
C140.0249 (8)0.0220 (8)0.0202 (8)0.0031 (7)0.0077 (7)0.0001 (6)
C150.0136 (7)0.0204 (8)0.0195 (7)0.0000 (6)0.0032 (6)0.0059 (6)
C160.0188 (8)0.0229 (8)0.0198 (7)0.0024 (6)0.0086 (6)0.0059 (6)
C170.0223 (8)0.0249 (8)0.0185 (7)0.0004 (7)0.0073 (6)0.0024 (6)
C180.0172 (8)0.0253 (8)0.0218 (8)0.0018 (6)0.0053 (6)0.0005 (7)
C190.0152 (7)0.0262 (9)0.0220 (8)0.0025 (6)0.0059 (6)0.0006 (7)
C200.0189 (8)0.0196 (8)0.0205 (8)0.0022 (6)0.0031 (6)0.0001 (6)
C210.0210 (8)0.0323 (10)0.0248 (8)0.0053 (7)0.0104 (7)0.0034 (7)
C220.0189 (8)0.0383 (10)0.0304 (9)0.0067 (7)0.0071 (7)0.0074 (8)
C230.0230 (9)0.0303 (10)0.0308 (9)0.0054 (7)0.0005 (7)0.0105 (8)
N30.0389 (10)0.0387 (10)0.0461 (11)0.0018 (8)0.0021 (9)0.0150 (8)
C240.0371 (11)0.0256 (9)0.0256 (9)0.0068 (8)0.0063 (8)0.0043 (7)
C250.0295 (10)0.0319 (10)0.0390 (11)0.0058 (8)0.0132 (8)0.0060 (8)
Geometric parameters (Å, º) top
Se1—C11.8498 (16)C10—C111.395 (2)
N1—C11.355 (2)C11—C141.508 (2)
N1—C21.482 (2)C12—H12A0.9800
N1—C61.4458 (19)C12—H12B0.9800
N2—C11.359 (2)C12—H12C0.9800
N2—C51.535 (5)C13—H13A0.9800
N2—C5B1.512 (3)C13—H13B0.9800
N2—C151.4469 (19)C13—H13C0.9800
C2—H2A0.9900C14—H14A0.9800
C2—H2B0.9900C14—H14B0.9800
C2—C31.518 (2)C14—H14C0.9800
C2—C3B1.518 (2)C15—C161.394 (2)
C3—H3A0.9900C15—C201.397 (2)
C3—H3B0.9900C16—C171.397 (2)
C3—C41.614 (5)C16—C211.508 (2)
C3B—H3BA0.9900C17—H170.9500
C3B—H3BB0.9900C17—C181.390 (2)
C3B—C4B1.507 (3)C18—C191.392 (2)
C4—H4A0.9900C18—C221.510 (2)
C4—H4B0.9900C19—H190.9500
C4—C51.506 (7)C19—C201.394 (2)
C4B—H4BA0.9900C20—C231.508 (2)
C4B—H4BB0.9900C21—H21A0.9800
C4B—C5B1.514 (4)C21—H21B0.9800
C5—H5A0.9900C21—H21C0.9800
C5—H5B0.9900C22—H22A0.9800
C5B—H5BA0.9900C22—H22B0.9800
C5B—H5BB0.9900C22—H22C0.9800
C6—C71.401 (2)C23—H23A0.9800
C6—C111.392 (2)C23—H23B0.9800
C7—C81.391 (2)C23—H23C0.9800
C7—C121.506 (2)N3—C241.144 (3)
C8—H80.9500C24—C251.455 (3)
C8—C91.394 (2)C25—H25A0.9800
C9—C101.392 (2)C25—H25B0.9800
C9—C131.510 (2)C25—H25C0.9800
C10—H100.9500
C1—N1—C2122.27 (13)C9—C10—C11121.73 (15)
C1—N1—C6119.78 (13)C11—C10—H10119.1
C6—N1—C2115.91 (12)C6—C11—C10118.38 (14)
C1—N2—C5114.8 (2)C6—C11—C14121.42 (14)
C1—N2—C5B129.74 (15)C10—C11—C14120.19 (14)
C1—N2—C15119.73 (13)C7—C12—H12A109.5
C15—N2—C5117.8 (2)C7—C12—H12B109.5
C15—N2—C5B110.40 (14)C7—C12—H12C109.5
N1—C1—Se1120.66 (11)H12A—C12—H12B109.5
N1—C1—N2118.10 (14)H12A—C12—H12C109.5
N2—C1—Se1121.23 (12)H12B—C12—H12C109.5
N1—C2—H2A108.8C9—C13—H13A109.5
N1—C2—H2B108.8C9—C13—H13B109.5
N1—C2—C3113.88 (13)C9—C13—H13C109.5
N1—C2—C3B113.88 (13)H13A—C13—H13B109.5
H2A—C2—H2B107.7H13A—C13—H13C109.5
C3—C2—H2A108.8H13B—C13—H13C109.5
C3—C2—H2B108.8C11—C14—H14A109.5
C2—C3—H3A110.5C11—C14—H14B109.5
C2—C3—H3B110.5C11—C14—H14C109.5
C2—C3—C4106.0 (2)H14A—C14—H14B109.5
H3A—C3—H3B108.7H14A—C14—H14C109.5
C4—C3—H3A110.5H14B—C14—H14C109.5
C4—C3—H3B110.5C16—C15—N2118.18 (15)
C2—C3B—H3BA109.4C16—C15—C20121.48 (14)
C2—C3B—H3BB109.4C20—C15—N2120.21 (15)
H3BA—C3B—H3BB108.0C15—C16—C17118.26 (15)
C4B—C3B—C2111.26 (16)C15—C16—C21121.24 (15)
C4B—C3B—H3BA109.4C17—C16—C21120.50 (15)
C4B—C3B—H3BB109.4C16—C17—H17119.1
C3—C4—H4A109.4C18—C17—C16121.90 (16)
C3—C4—H4B109.4C18—C17—H17119.1
H4A—C4—H4B108.0C17—C18—C19118.17 (15)
C5—C4—C3111.3 (4)C17—C18—C22121.67 (16)
C5—C4—H4A109.4C19—C18—C22120.16 (16)
C5—C4—H4B109.4C18—C19—H19119.0
C3B—C4B—H4BA109.6C18—C19—C20121.92 (16)
C3B—C4B—H4BB109.6C20—C19—H19119.0
C3B—C4B—C5B110.3 (2)C15—C20—C23121.44 (15)
H4BA—C4B—H4BB108.1C19—C20—C15118.26 (15)
C5B—C4B—H4BA109.6C19—C20—C23120.27 (15)
C5B—C4B—H4BB109.6C16—C21—H21A109.5
N2—C5—H5A109.4C16—C21—H21B109.5
N2—C5—H5B109.4C16—C21—H21C109.5
C4—C5—N2111.1 (4)H21A—C21—H21B109.5
C4—C5—H5A109.4H21A—C21—H21C109.5
C4—C5—H5B109.4H21B—C21—H21C109.5
H5A—C5—H5B108.0C18—C22—H22A109.5
N2—C5B—C4B112.3 (2)C18—C22—H22B109.5
N2—C5B—H5BA109.1C18—C22—H22C109.5
N2—C5B—H5BB109.1H22A—C22—H22B109.5
C4B—C5B—H5BA109.1H22A—C22—H22C109.5
C4B—C5B—H5BB109.1H22B—C22—H22C109.5
H5BA—C5B—H5BB107.9C20—C23—H23A109.5
C7—C6—N1118.94 (14)C20—C23—H23B109.5
C11—C6—N1119.57 (14)C20—C23—H23C109.5
C11—C6—C7121.46 (14)H23A—C23—H23B109.5
C6—C7—C12121.36 (14)H23A—C23—H23C109.5
C8—C7—C6118.34 (14)H23B—C23—H23C109.5
C8—C7—C12120.27 (14)N3—C24—C25178.7 (2)
C7—C8—H8119.2C24—C25—H25A109.5
C7—C8—C9121.70 (15)C24—C25—H25B109.5
C9—C8—H8119.2C24—C25—H25C109.5
C8—C9—C13120.60 (15)H25A—C25—H25B109.5
C10—C9—C8118.34 (14)H25A—C25—H25C109.5
C10—C9—C13121.03 (15)H25B—C25—H25C109.5
C9—C10—H10119.1
N1—C2—C3—C476.4 (2)C5B—N2—C15—C2088.8 (2)
N1—C2—C3B—C4B42.9 (2)C6—N1—C1—Se18.35 (19)
N1—C6—C7—C8179.80 (14)C6—N1—C1—N2172.24 (14)
N1—C6—C7—C122.2 (2)C6—N1—C2—C3112.40 (15)
N1—C6—C11—C10179.43 (14)C6—N1—C2—C3B112.40 (15)
N1—C6—C11—C141.6 (2)C6—C7—C8—C90.0 (2)
N2—C15—C16—C17175.44 (14)C7—C6—C11—C101.5 (2)
N2—C15—C16—C215.4 (2)C7—C6—C11—C14179.52 (15)
N2—C15—C20—C19176.33 (14)C7—C8—C9—C102.1 (2)
N2—C15—C20—C235.6 (2)C7—C8—C9—C13175.77 (15)
C1—N1—C2—C383.91 (18)C8—C9—C10—C112.5 (2)
C1—N1—C2—C3B83.91 (18)C9—C10—C11—C60.7 (2)
C1—N1—C6—C791.48 (18)C9—C10—C11—C14178.26 (15)
C1—N1—C6—C1190.54 (18)C11—C6—C7—C81.9 (2)
C1—N2—C5—C490.9 (4)C11—C6—C7—C12179.83 (15)
C1—N2—C5B—C4B28.1 (4)C12—C7—C8—C9177.99 (15)
C1—N2—C15—C1689.25 (19)C13—C9—C10—C11175.38 (14)
C1—N2—C15—C2094.90 (19)C15—N2—C1—Se118.5 (2)
C2—N1—C1—Se1154.72 (12)C15—N2—C1—N1160.95 (14)
C2—N1—C1—N224.7 (2)C15—N2—C5—C4119.6 (3)
C2—N1—C6—C772.64 (18)C15—N2—C5B—C4B156.2 (2)
C2—N1—C6—C11105.35 (16)C15—C16—C17—C181.1 (2)
C2—C3—C4—C563.8 (4)C16—C15—C20—C190.6 (2)
C2—C3B—C4B—C5B43.9 (3)C16—C15—C20—C23178.66 (16)
C3—C4—C5—N276.3 (5)C16—C17—C18—C190.9 (3)
C3B—C4B—C5B—N282.9 (3)C16—C17—C18—C22179.05 (16)
C5—N2—C1—Se1130.4 (2)C17—C18—C19—C200.1 (3)
C5—N2—C1—N150.2 (3)C18—C19—C20—C150.9 (3)
C5—N2—C15—C16122.8 (3)C18—C19—C20—C23178.94 (16)
C5—N2—C15—C2053.0 (3)C20—C15—C16—C170.4 (2)
C5B—N2—C1—Se1166.11 (19)C20—C15—C16—C21178.83 (15)
C5B—N2—C1—N114.5 (3)C21—C16—C17—C18178.05 (16)
C5B—N2—C15—C1687.0 (2)C22—C18—C19—C20179.91 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4A···Se1i0.993.094.009 (6)155
C4—H4B···Se1ii0.992.913.737 (4)141
C4B—H4BB···Se1ii0.993.153.965 (3)141
C25—H25B···Se1iii0.983.033.829 (2)140
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x+1, y1/2, z+3/2; (iii) x+1, y+1, z+1.
(SDiazMesSI2) top
Crystal data top
C23H30I2N2SZ = 2
Mr = 620.35F(000) = 608
Triclinic, P1Dx = 1.694 Mg m3
a = 7.9505 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.5048 (4) ÅCell parameters from 9861 reflections
c = 18.2812 (9) Åθ = 2.3–27.3°
α = 81.040 (3)°µ = 2.68 mm1
β = 89.926 (2)°T = 100 K
γ = 85.125 (2)°Plate, red
V = 1216.54 (10) Å30.17 × 0.12 × 0.08 mm
Data collection top
Bruker D8 Venture Photon 2
diffractometer
4834 reflections with I > 2σ(I)
Radiation source: Incoatec IµSRint = 0.067
φ and ω scansθmax = 27.4°, θmin = 2.4°
Absorption correction: multi-scan
SADABS v2016/2 (Bruker AXS Inc., 2017)
h = 1010
Tmin = 0.636, Tmax = 0.746k = 1010
37544 measured reflectionsl = 2323
5455 independent reflections
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.072H-atom parameters constrained
S = 1.12 w = 1/[σ2(Fo2) + (0.0141P)2 + 2.7069P]
where P = (Fo2 + 2Fc2)/3
5455 reflections(Δ/σ)max = 0.001
259 parametersΔρmax = 1.35 e Å3
0 restraintsΔρmin = 1.40 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
I10.28705 (3)0.88440 (3)0.22530 (2)0.01492 (7)
I20.06264 (3)1.09545 (3)0.12352 (2)0.02728 (8)
S10.47932 (10)0.66975 (11)0.31875 (5)0.01703 (18)
N10.8088 (3)0.6376 (3)0.33943 (15)0.0127 (6)
N20.7225 (3)0.6387 (3)0.21680 (15)0.0130 (6)
C10.6852 (4)0.6480 (4)0.28741 (19)0.0134 (7)
C20.9843 (4)0.5614 (4)0.3374 (2)0.0168 (7)
H2A1.0181070.5094550.3881670.020*
H2B1.0610920.6459790.3221320.020*
C31.0080 (5)0.4375 (5)0.2856 (2)0.0213 (8)
H3A1.1145300.3701210.2989130.026*
H3B0.9141800.3673980.2926140.026*
C41.0133 (4)0.5118 (5)0.2043 (2)0.0196 (8)
H4A1.1299030.5378510.1916070.024*
H4B0.9813900.4337130.1730790.024*
C50.8946 (4)0.6622 (4)0.18810 (19)0.0158 (7)
H5A0.9411710.7479170.2107230.019*
H5B0.8875690.6973750.1338820.019*
C60.7742 (4)0.7057 (4)0.40671 (18)0.0139 (7)
C70.7426 (4)0.6058 (4)0.47232 (19)0.0159 (7)
C80.7116 (4)0.6771 (5)0.53581 (19)0.0179 (7)
H80.6866110.6119120.5808890.021*
C90.7166 (5)0.8403 (5)0.5346 (2)0.0207 (8)
C100.7539 (5)0.9335 (5)0.4683 (2)0.0208 (8)
H100.7602781.0448300.4673240.025*
C110.7822 (4)0.8702 (4)0.4034 (2)0.0168 (7)
C120.7344 (5)0.4291 (4)0.4761 (2)0.0220 (8)
H12A0.6871980.4072520.4295890.033*
H12B0.6623100.3895090.5172850.033*
H12C0.8482210.3750110.4839660.033*
C130.6858 (6)0.9149 (5)0.6037 (2)0.0301 (9)
H13A0.7938360.9368110.6239550.045*
H13B0.6294850.8413230.6404750.045*
H13C0.6139191.0150730.5913600.045*
C140.8136 (5)0.9761 (5)0.3316 (2)0.0244 (8)
H14A0.9204520.9383950.3108050.037*
H14B0.8195681.0860620.3407140.037*
H14C0.7211990.9727940.2966180.037*
C150.5972 (4)0.6111 (4)0.16372 (18)0.0128 (7)
C160.5322 (4)0.4619 (4)0.16910 (19)0.0144 (7)
C170.4114 (4)0.4417 (4)0.11705 (19)0.0150 (7)
H170.3650810.3414560.1205770.018*
C180.3563 (4)0.5630 (5)0.0602 (2)0.0185 (7)
C190.4284 (4)0.7073 (4)0.05493 (19)0.0173 (7)
H190.3942630.7902400.0153990.021*
C200.5490 (4)0.7349 (4)0.10561 (19)0.0154 (7)
C210.5925 (5)0.3234 (4)0.2275 (2)0.0197 (7)
H21A0.5224200.2346310.2257130.030*
H21B0.5840810.3564880.2764350.030*
H21C0.7103580.2888640.2182210.030*
C220.2198 (4)0.5396 (5)0.0072 (2)0.0219 (8)
H22A0.1941990.4275200.0156510.033*
H22B0.2581250.5678360.0437930.033*
H22C0.1180650.6080650.0150520.033*
C230.6172 (5)0.8963 (4)0.0964 (2)0.0204 (8)
H23A0.6655700.9129930.1436180.031*
H23B0.5255130.9793780.0810820.031*
H23C0.7048900.9017650.0586230.031*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.01112 (11)0.01644 (12)0.01866 (12)0.00050 (8)0.00204 (8)0.00765 (9)
I20.02175 (13)0.01754 (13)0.03991 (17)0.00034 (10)0.00680 (11)0.00272 (11)
S10.0101 (4)0.0260 (5)0.0145 (4)0.0008 (3)0.0011 (3)0.0028 (4)
N10.0117 (13)0.0123 (14)0.0134 (14)0.0019 (11)0.0013 (10)0.0015 (11)
N20.0102 (13)0.0167 (15)0.0129 (14)0.0022 (11)0.0026 (10)0.0039 (11)
C10.0127 (15)0.0128 (16)0.0150 (16)0.0002 (12)0.0018 (12)0.0035 (13)
C20.0105 (15)0.0200 (18)0.0193 (18)0.0027 (13)0.0015 (13)0.0035 (14)
C30.0172 (17)0.0200 (19)0.026 (2)0.0055 (14)0.0001 (14)0.0046 (16)
C40.0116 (16)0.023 (2)0.0254 (19)0.0040 (14)0.0029 (14)0.0103 (16)
C50.0084 (15)0.0220 (19)0.0171 (17)0.0031 (13)0.0049 (12)0.0023 (14)
C60.0106 (15)0.0165 (18)0.0143 (16)0.0030 (13)0.0024 (12)0.0039 (14)
C70.0125 (15)0.0174 (18)0.0172 (17)0.0005 (13)0.0023 (13)0.0022 (14)
C80.0162 (16)0.0224 (19)0.0130 (16)0.0017 (14)0.0005 (13)0.0016 (14)
C90.0208 (18)0.024 (2)0.0184 (18)0.0040 (15)0.0034 (14)0.0098 (15)
C100.0250 (18)0.0154 (18)0.0232 (19)0.0015 (14)0.0003 (15)0.0084 (15)
C110.0143 (16)0.0163 (18)0.0198 (18)0.0015 (13)0.0004 (13)0.0043 (14)
C120.0261 (19)0.0162 (19)0.024 (2)0.0016 (15)0.0023 (15)0.0035 (15)
C130.037 (2)0.035 (2)0.019 (2)0.0080 (19)0.0023 (17)0.0148 (18)
C140.033 (2)0.017 (2)0.023 (2)0.0012 (16)0.0029 (16)0.0035 (16)
C150.0097 (14)0.0182 (17)0.0110 (15)0.0011 (13)0.0020 (12)0.0042 (13)
C160.0145 (16)0.0129 (17)0.0157 (16)0.0011 (13)0.0042 (13)0.0031 (13)
C170.0099 (15)0.0188 (18)0.0188 (17)0.0010 (13)0.0052 (13)0.0105 (14)
C180.0108 (15)0.030 (2)0.0164 (17)0.0016 (14)0.0037 (13)0.0099 (15)
C190.0177 (16)0.0196 (18)0.0129 (16)0.0047 (14)0.0007 (13)0.0006 (14)
C200.0161 (16)0.0148 (17)0.0152 (17)0.0001 (13)0.0037 (13)0.0028 (14)
C210.0192 (17)0.0149 (18)0.0244 (19)0.0013 (14)0.0011 (14)0.0011 (15)
C220.0167 (17)0.030 (2)0.0205 (19)0.0012 (15)0.0009 (14)0.0074 (16)
C230.0212 (18)0.0188 (19)0.0205 (19)0.0003 (14)0.0026 (14)0.0015 (15)
Geometric parameters (Å, º) top
I1—I22.8794 (4)C11—C141.505 (5)
I1—S12.6738 (9)C12—H12A0.9800
S1—C11.738 (3)C12—H12B0.9800
N1—C11.356 (4)C12—H12C0.9800
N1—C21.491 (4)C13—H13A0.9800
N1—C61.455 (4)C13—H13B0.9800
N2—C11.337 (4)C13—H13C0.9800
N2—C51.483 (4)C14—H14A0.9800
N2—C151.449 (4)C14—H14B0.9800
C2—H2A0.9900C14—H14C0.9800
C2—H2B0.9900C15—C161.400 (5)
C2—C31.524 (5)C15—C201.402 (5)
C3—H3A0.9900C16—C171.393 (5)
C3—H3B0.9900C16—C211.507 (5)
C3—C41.523 (5)C17—H170.9500
C4—H4A0.9900C17—C181.388 (5)
C4—H4B0.9900C18—C191.389 (5)
C4—C51.514 (5)C18—C221.502 (5)
C5—H5A0.9900C19—H190.9500
C5—H5B0.9900C19—C201.393 (5)
C6—C71.393 (5)C20—C231.504 (5)
C6—C111.398 (5)C21—H21A0.9800
C7—C81.403 (5)C21—H21B0.9800
C7—C121.501 (5)C21—H21C0.9800
C8—H80.9500C22—H22A0.9800
C8—C91.388 (5)C22—H22B0.9800
C9—C101.388 (5)C22—H22C0.9800
C9—C131.509 (5)C23—H23A0.9800
C10—H100.9500C23—H23B0.9800
C10—C111.388 (5)C23—H23C0.9800
S1—I1—I2175.38 (2)C7—C12—H12B109.5
C1—S1—I1111.45 (12)C7—C12—H12C109.5
C1—N1—C2127.7 (3)H12A—C12—H12B109.5
C1—N1—C6119.4 (3)H12A—C12—H12C109.5
C6—N1—C2112.9 (3)H12B—C12—H12C109.5
C1—N2—C5121.2 (3)C9—C13—H13A109.5
C1—N2—C15122.3 (3)C9—C13—H13B109.5
C15—N2—C5116.4 (3)C9—C13—H13C109.5
N1—C1—S1116.0 (2)H13A—C13—H13B109.5
N2—C1—S1123.0 (2)H13A—C13—H13C109.5
N2—C1—N1121.0 (3)H13B—C13—H13C109.5
N1—C2—H2A108.6C11—C14—H14A109.5
N1—C2—H2B108.6C11—C14—H14B109.5
N1—C2—C3114.6 (3)C11—C14—H14C109.5
H2A—C2—H2B107.6H14A—C14—H14B109.5
C3—C2—H2A108.6H14A—C14—H14C109.5
C3—C2—H2B108.6H14B—C14—H14C109.5
C2—C3—H3A109.0C16—C15—N2120.3 (3)
C2—C3—H3B109.0C16—C15—C20121.3 (3)
H3A—C3—H3B107.8C20—C15—N2118.4 (3)
C4—C3—C2113.0 (3)C15—C16—C21122.2 (3)
C4—C3—H3A109.0C17—C16—C15118.1 (3)
C4—C3—H3B109.0C17—C16—C21119.7 (3)
C3—C4—H4A109.4C16—C17—H17118.9
C3—C4—H4B109.4C18—C17—C16122.3 (3)
H4A—C4—H4B108.0C18—C17—H17118.9
C5—C4—C3111.4 (3)C17—C18—C19118.0 (3)
C5—C4—H4A109.4C17—C18—C22120.8 (3)
C5—C4—H4B109.4C19—C18—C22121.2 (3)
N2—C5—C4112.6 (3)C18—C19—H19118.8
N2—C5—H5A109.1C18—C19—C20122.3 (3)
N2—C5—H5B109.1C20—C19—H19118.8
C4—C5—H5A109.1C15—C20—C23123.5 (3)
C4—C5—H5B109.1C19—C20—C15117.9 (3)
H5A—C5—H5B107.8C19—C20—C23118.5 (3)
C7—C6—N1119.7 (3)C16—C21—H21A109.5
C7—C6—C11122.3 (3)C16—C21—H21B109.5
C11—C6—N1117.9 (3)C16—C21—H21C109.5
C6—C7—C8117.5 (3)H21A—C21—H21B109.5
C6—C7—C12122.5 (3)H21A—C21—H21C109.5
C8—C7—C12120.0 (3)H21B—C21—H21C109.5
C7—C8—H8119.1C18—C22—H22A109.5
C9—C8—C7121.9 (3)C18—C22—H22B109.5
C9—C8—H8119.1C18—C22—H22C109.5
C8—C9—C10118.2 (3)H22A—C22—H22B109.5
C8—C9—C13121.3 (4)H22A—C22—H22C109.5
C10—C9—C13120.5 (4)H22B—C22—H22C109.5
C9—C10—H10118.7C20—C23—H23A109.5
C11—C10—C9122.5 (3)C20—C23—H23B109.5
C11—C10—H10118.7C20—C23—H23C109.5
C6—C11—C14121.4 (3)H23A—C23—H23B109.5
C10—C11—C6117.5 (3)H23A—C23—H23C109.5
C10—C11—C14121.1 (3)H23B—C23—H23C109.5
C7—C12—H12A109.5
I1—S1—C1—N1137.9 (2)C6—N1—C2—C3158.0 (3)
I1—S1—C1—N243.2 (3)C6—C7—C8—C91.8 (5)
N1—C2—C3—C476.3 (4)C7—C6—C11—C101.3 (5)
N1—C6—C7—C8179.3 (3)C7—C6—C11—C14178.9 (3)
N1—C6—C7—C123.0 (5)C7—C8—C9—C100.2 (5)
N1—C6—C11—C10178.2 (3)C7—C8—C9—C13179.0 (3)
N1—C6—C11—C144.2 (5)C8—C9—C10—C111.5 (5)
N2—C15—C16—C17179.6 (3)C9—C10—C11—C60.8 (5)
N2—C15—C16—C212.2 (5)C9—C10—C11—C14176.8 (4)
N2—C15—C20—C19179.9 (3)C11—C6—C7—C82.6 (5)
N2—C15—C20—C231.6 (5)C11—C6—C7—C12179.8 (3)
C1—N1—C2—C321.6 (5)C12—C7—C8—C9179.5 (3)
C1—N1—C6—C7102.1 (4)C13—C9—C10—C11179.6 (3)
C1—N1—C6—C1181.0 (4)C15—N2—C1—S113.8 (5)
C1—N2—C5—C483.1 (4)C15—N2—C1—N1165.0 (3)
C1—N2—C15—C1670.4 (4)C15—N2—C5—C499.0 (3)
C1—N2—C15—C20112.3 (4)C15—C16—C17—C180.9 (5)
C2—N1—C1—S1155.4 (3)C16—C15—C20—C192.8 (5)
C2—N1—C1—N223.4 (5)C16—C15—C20—C23178.9 (3)
C2—N1—C6—C777.6 (4)C16—C17—C18—C191.5 (5)
C2—N1—C6—C1199.3 (3)C16—C17—C18—C22177.1 (3)
C2—C3—C4—C535.7 (4)C17—C18—C19—C201.8 (5)
C3—C4—C5—N249.8 (4)C18—C19—C20—C150.2 (5)
C5—N2—C1—S1164.0 (3)C18—C19—C20—C23178.6 (3)
C5—N2—C1—N117.2 (5)C20—C15—C16—C173.1 (5)
C5—N2—C15—C16111.8 (3)C20—C15—C16—C21175.0 (3)
C5—N2—C15—C2065.6 (4)C21—C16—C17—C18177.2 (3)
C6—N1—C1—S124.2 (4)C22—C18—C19—C20176.7 (3)
C6—N1—C1—N2157.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2B···I1i0.993.164.111 (4)162
C4—H4B···I2ii0.993.164.034 (4)148
C5—H5A···I1i0.993.103.896 (3)138
Symmetry codes: (i) x+1, y, z; (ii) x+1, y1, z.
(SDiazMesSeI2) top
Crystal data top
C23H30I2N2SeZ = 2
Mr = 667.25F(000) = 644
Triclinic, P1Dx = 1.809 Mg m3
a = 8.0282 (6) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.4305 (8) ÅCell parameters from 9806 reflections
c = 18.3525 (16) Åθ = 2.5–30.6°
α = 81.814 (4)°µ = 4.06 mm1
β = 89.706 (4)°T = 100 K
γ = 85.171 (4)°Block, red
V = 1225.08 (18) Å30.19 × 0.15 × 0.13 mm
Data collection top
Bruker D8 Venture Photon 2
diffractometer
6504 reflections with I > 2σ(I)
Radiation source: Incoatec IµSRint = 0.045
φ and ω scansθmax = 30.6°, θmin = 2.2°
Absorption correction: multi-scan
SADABS v2016/2 (Bruker AXS Inc., 2017)
h = 1111
Tmin = 0.634, Tmax = 0.746k = 1212
53696 measured reflectionsl = 2626
7479 independent reflections
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.023Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.049H-atom parameters constrained
S = 1.10 w = 1/[σ2(Fo2) + (0.0078P)2 + 1.5207P]
where P = (Fo2 + 2Fc2)/3
7479 reflections(Δ/σ)max = 0.002
259 parametersΔρmax = 0.70 e Å3
0 restraintsΔρmin = 0.75 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
I10.27703 (2)0.89168 (2)0.22239 (2)0.01494 (3)
I20.05678 (2)1.09633 (2)0.11610 (2)0.02769 (4)
Se10.46782 (2)0.67455 (3)0.32117 (2)0.01656 (5)
N10.7225 (2)0.6396 (2)0.21435 (9)0.0130 (3)
N20.8114 (2)0.6379 (2)0.33598 (9)0.0135 (3)
C10.6888 (2)0.6496 (2)0.28490 (10)0.0126 (3)
C20.8921 (2)0.6648 (3)0.18439 (11)0.0171 (4)
H2A0.9389190.7508320.2073880.020*
H2B0.8831190.7011630.1307320.020*
C31.0104 (3)0.5134 (3)0.19820 (12)0.0213 (4)
H3A1.1251880.5398140.1841490.026*
H3B0.9766980.4344850.1671930.026*
C41.0091 (3)0.4392 (3)0.27921 (12)0.0213 (4)
H4A0.9175980.3670270.2869610.026*
H4B1.1158610.3731580.2912580.026*
C50.9859 (2)0.5642 (3)0.33123 (11)0.0174 (4)
H5A1.0230100.5132720.3810950.021*
H5B1.0594960.6509510.3151690.021*
C60.5966 (2)0.6117 (2)0.16227 (10)0.0124 (3)
C70.5467 (2)0.7364 (2)0.10569 (11)0.0153 (4)
C80.4260 (2)0.7074 (3)0.05574 (11)0.0166 (4)
H80.3905800.7904580.0170580.020*
C90.3562 (2)0.5609 (3)0.06083 (11)0.0161 (4)
C100.4131 (2)0.4383 (3)0.11640 (11)0.0152 (4)
H100.3680150.3369600.1196530.018*
C110.5342 (2)0.4601 (2)0.16731 (11)0.0142 (4)
C120.6139 (3)0.8991 (3)0.09724 (12)0.0195 (4)
H12A0.6594270.9173170.1445020.029*
H12B0.5234850.9822090.0814620.029*
H12C0.7024740.9037820.0602560.029*
C130.2204 (3)0.5367 (3)0.00849 (12)0.0211 (4)
H13A0.2607930.5571170.0421900.032*
H13B0.1226230.6112840.0145370.032*
H13C0.1892950.4258220.0189700.032*
C140.5958 (3)0.3205 (3)0.22395 (12)0.0195 (4)
H14A0.5235490.2325640.2234960.029*
H14B0.5932900.3547080.2728230.029*
H14C0.7105850.2834920.2123890.029*
C150.7790 (2)0.7038 (2)0.40398 (10)0.0143 (4)
C160.7841 (3)0.8691 (3)0.40316 (12)0.0177 (4)
C170.7552 (3)0.9309 (3)0.46878 (12)0.0219 (4)
H170.7589661.0430680.4692320.026*
C180.7208 (3)0.8329 (3)0.53399 (12)0.0214 (4)
C190.7181 (3)0.6689 (3)0.53267 (11)0.0191 (4)
H190.6946400.6011880.5768130.023*
C200.7489 (2)0.6004 (3)0.46836 (11)0.0162 (4)
C210.8131 (3)0.9791 (3)0.33286 (13)0.0246 (5)
H21A0.9152780.9394460.3094260.037*
H21B0.8250831.0878430.3440060.037*
H21C0.7178560.9814460.2994300.037*
C220.6869 (4)0.9050 (3)0.60399 (13)0.0334 (6)
H22A0.6269060.8309490.6386110.050*
H22B0.6188101.0075660.5925760.050*
H22C0.7931680.9232960.6261770.050*
C230.7446 (3)0.4213 (3)0.46971 (12)0.0215 (4)
H23A0.6998970.3999990.4227950.032*
H23B0.6730190.3787790.5099950.032*
H23C0.8580930.3689040.4772010.032*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.01234 (6)0.01620 (6)0.01713 (6)0.00217 (4)0.00048 (4)0.00470 (5)
I20.02417 (8)0.01847 (7)0.03804 (9)0.00253 (5)0.01007 (6)0.00498 (6)
Se10.01164 (9)0.02445 (11)0.01261 (9)0.00002 (7)0.00115 (7)0.00026 (8)
N10.0114 (7)0.0165 (8)0.0117 (7)0.0045 (6)0.0011 (6)0.0020 (6)
N20.0130 (7)0.0155 (8)0.0116 (7)0.0012 (6)0.0012 (6)0.0008 (6)
C10.0122 (8)0.0121 (9)0.0130 (9)0.0012 (7)0.0004 (7)0.0000 (7)
C20.0134 (9)0.0242 (11)0.0145 (9)0.0060 (8)0.0032 (7)0.0032 (8)
C30.0166 (9)0.0268 (12)0.0225 (11)0.0011 (8)0.0042 (8)0.0107 (9)
C40.0170 (9)0.0206 (11)0.0260 (11)0.0038 (8)0.0004 (8)0.0049 (9)
C50.0133 (9)0.0213 (10)0.0169 (9)0.0009 (7)0.0011 (7)0.0017 (8)
C60.0112 (8)0.0161 (9)0.0103 (8)0.0019 (7)0.0004 (6)0.0022 (7)
C70.0150 (9)0.0173 (10)0.0134 (9)0.0024 (7)0.0020 (7)0.0013 (7)
C80.0149 (9)0.0217 (10)0.0121 (9)0.0000 (7)0.0012 (7)0.0002 (7)
C90.0118 (8)0.0235 (10)0.0137 (9)0.0010 (7)0.0002 (7)0.0049 (8)
C100.0123 (8)0.0176 (10)0.0160 (9)0.0029 (7)0.0002 (7)0.0026 (7)
C110.0125 (8)0.0175 (10)0.0126 (9)0.0014 (7)0.0005 (7)0.0015 (7)
C120.0222 (10)0.0168 (10)0.0186 (10)0.0044 (8)0.0001 (8)0.0021 (8)
C130.0150 (9)0.0325 (12)0.0167 (10)0.0051 (8)0.0030 (7)0.0047 (9)
C140.0192 (10)0.0179 (10)0.0206 (10)0.0033 (8)0.0040 (8)0.0018 (8)
C150.0134 (8)0.0181 (10)0.0113 (8)0.0001 (7)0.0016 (7)0.0020 (7)
C160.0180 (9)0.0168 (10)0.0177 (10)0.0005 (7)0.0029 (7)0.0005 (8)
C170.0285 (11)0.0161 (10)0.0218 (11)0.0003 (8)0.0027 (9)0.0058 (8)
C180.0211 (10)0.0270 (12)0.0160 (10)0.0050 (8)0.0039 (8)0.0065 (8)
C190.0192 (9)0.0256 (11)0.0109 (9)0.0007 (8)0.0022 (7)0.0008 (8)
C200.0147 (9)0.0196 (10)0.0139 (9)0.0014 (7)0.0024 (7)0.0013 (7)
C210.0358 (13)0.0156 (10)0.0216 (11)0.0037 (9)0.0030 (9)0.0010 (8)
C220.0445 (15)0.0367 (15)0.0196 (11)0.0087 (12)0.0030 (10)0.0130 (10)
C230.0263 (11)0.0192 (11)0.0183 (10)0.0052 (8)0.0025 (8)0.0017 (8)
Geometric parameters (Å, º) top
I1—I22.9107 (3)C11—C141.506 (3)
I1—Se12.7558 (3)C12—H12A0.9800
Se1—C11.8974 (19)C12—H12B0.9800
N1—C11.334 (2)C12—H12C0.9800
N1—C21.487 (2)C13—H13A0.9800
N1—C61.450 (2)C13—H13B0.9800
N2—C11.351 (2)C13—H13C0.9800
N2—C51.491 (3)C14—H14A0.9800
N2—C151.450 (2)C14—H14B0.9800
C2—H2A0.9900C14—H14C0.9800
C2—H2B0.9900C15—C161.396 (3)
C2—C31.517 (3)C15—C201.398 (3)
C3—H3A0.9900C16—C171.390 (3)
C3—H3B0.9900C16—C211.507 (3)
C3—C41.529 (3)C17—H170.9500
C4—H4A0.9900C17—C181.394 (3)
C4—H4B0.9900C18—C191.388 (3)
C4—C51.519 (3)C18—C221.512 (3)
C5—H5A0.9900C19—H190.9500
C5—H5B0.9900C19—C201.398 (3)
C6—C71.402 (3)C20—C231.509 (3)
C6—C111.403 (3)C21—H21A0.9800
C7—C81.397 (3)C21—H21B0.9800
C7—C121.503 (3)C21—H21C0.9800
C8—H80.9500C22—H22A0.9800
C8—C91.390 (3)C22—H22B0.9800
C9—C101.393 (3)C22—H22C0.9800
C9—C131.502 (3)C23—H23A0.9800
C10—H100.9500C23—H23B0.9800
C10—C111.392 (3)C23—H23C0.9800
Se1—I1—I2174.620 (7)C7—C12—H12B109.5
C1—Se1—I1109.28 (6)C7—C12—H12C109.5
C1—N1—C2120.77 (16)H12A—C12—H12B109.5
C1—N1—C6122.74 (16)H12A—C12—H12C109.5
C6—N1—C2116.43 (15)H12B—C12—H12C109.5
C1—N2—C5127.28 (17)C9—C13—H13A109.5
C1—N2—C15119.63 (16)C9—C13—H13B109.5
C15—N2—C5113.08 (15)C9—C13—H13C109.5
N1—C1—Se1122.92 (14)H13A—C13—H13B109.5
N1—C1—N2121.70 (17)H13A—C13—H13C109.5
N2—C1—Se1115.36 (14)H13B—C13—H13C109.5
N1—C2—H2A109.1C11—C14—H14A109.5
N1—C2—H2B109.1C11—C14—H14B109.5
N1—C2—C3112.44 (17)C11—C14—H14C109.5
H2A—C2—H2B107.8H14A—C14—H14B109.5
C3—C2—H2A109.1H14A—C14—H14C109.5
C3—C2—H2B109.1H14B—C14—H14C109.5
C2—C3—H3A109.4C16—C15—N2118.39 (18)
C2—C3—H3B109.4C16—C15—C20122.13 (18)
C2—C3—C4110.98 (17)C20—C15—N2119.45 (18)
H3A—C3—H3B108.0C15—C16—C21121.32 (19)
C4—C3—H3A109.4C17—C16—C15118.01 (19)
C4—C3—H3B109.4C17—C16—C21120.6 (2)
C3—C4—H4A109.0C16—C17—H17119.1
C3—C4—H4B109.0C16—C17—C18121.9 (2)
H4A—C4—H4B107.8C18—C17—H17119.1
C5—C4—C3112.99 (18)C17—C18—C22120.3 (2)
C5—C4—H4A109.0C19—C18—C17118.4 (2)
C5—C4—H4B109.0C19—C18—C22121.3 (2)
N2—C5—C4114.95 (17)C18—C19—H19119.0
N2—C5—H5A108.5C18—C19—C20122.0 (2)
N2—C5—H5B108.5C20—C19—H19119.0
C4—C5—H5A108.5C15—C20—C19117.57 (19)
C4—C5—H5B108.5C15—C20—C23122.36 (18)
H5A—C5—H5B107.5C19—C20—C23120.05 (19)
C7—C6—N1118.43 (17)C16—C21—H21A109.5
C7—C6—C11121.73 (17)C16—C21—H21B109.5
C11—C6—N1119.76 (17)C16—C21—H21C109.5
C6—C7—C12123.38 (18)H21A—C21—H21B109.5
C8—C7—C6117.75 (18)H21A—C21—H21C109.5
C8—C7—C12118.87 (19)H21B—C21—H21C109.5
C7—C8—H8118.9C18—C22—H22A109.5
C9—C8—C7122.10 (19)C18—C22—H22B109.5
C9—C8—H8118.9C18—C22—H22C109.5
C8—C9—C10118.37 (18)H22A—C22—H22B109.5
C8—C9—C13120.66 (19)H22A—C22—H22C109.5
C10—C9—C13120.95 (19)H22B—C22—H22C109.5
C9—C10—H10119.0C20—C23—H23A109.5
C11—C10—C9121.95 (19)C20—C23—H23B109.5
C11—C10—H10119.0C20—C23—H23C109.5
C6—C11—C14122.70 (17)H23A—C23—H23B109.5
C10—C11—C6118.00 (18)H23A—C23—H23C109.5
C10—C11—C14119.28 (18)H23B—C23—H23C109.5
C7—C12—H12A109.5
I1—Se1—C1—N141.46 (18)C6—N1—C2—C398.8 (2)
I1—Se1—C1—N2140.31 (13)C6—C7—C8—C90.1 (3)
N1—C2—C3—C450.7 (2)C7—C6—C11—C103.4 (3)
N1—C6—C7—C8179.68 (17)C7—C6—C11—C14175.07 (19)
N1—C6—C7—C121.6 (3)C7—C8—C9—C102.0 (3)
N1—C6—C11—C10179.81 (17)C7—C8—C9—C13176.87 (19)
N1—C6—C11—C141.7 (3)C8—C9—C10—C111.4 (3)
N2—C15—C16—C17179.11 (18)C9—C10—C11—C61.2 (3)
N2—C15—C16—C213.3 (3)C9—C10—C11—C14177.31 (19)
N2—C15—C20—C19179.96 (17)C11—C6—C7—C82.8 (3)
N2—C15—C20—C231.6 (3)C11—C6—C7—C12178.41 (19)
C1—N1—C2—C384.0 (2)C12—C7—C8—C9178.89 (19)
C1—N1—C6—C7111.8 (2)C13—C9—C10—C11177.44 (19)
C1—N1—C6—C1171.3 (3)C15—N2—C1—Se123.4 (2)
C1—N2—C5—C424.0 (3)C15—N2—C1—N1158.31 (18)
C1—N2—C15—C1679.9 (2)C15—N2—C5—C4156.80 (18)
C1—N2—C15—C20102.1 (2)C15—C16—C17—C180.4 (3)
C2—N1—C1—Se1163.19 (15)C16—C15—C20—C192.1 (3)
C2—N1—C1—N218.7 (3)C16—C15—C20—C23179.51 (19)
C2—N1—C6—C765.4 (2)C16—C17—C18—C190.9 (3)
C2—N1—C6—C11111.5 (2)C16—C17—C18—C22178.9 (2)
C2—C3—C4—C534.7 (2)C17—C18—C19—C200.1 (3)
C3—C4—C5—N276.8 (2)C18—C19—C20—C151.5 (3)
C5—N2—C1—Se1157.43 (16)C18—C19—C20—C23180.0 (2)
C5—N2—C1—N120.8 (3)C20—C15—C16—C171.1 (3)
C5—N2—C15—C1699.3 (2)C20—C15—C16—C21178.7 (2)
C5—N2—C15—C2078.7 (2)C21—C16—C17—C18177.2 (2)
C6—N1—C1—Se113.8 (3)C22—C18—C19—C20179.9 (2)
C6—N1—C1—N2164.29 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2A···I1i0.993.083.885 (2)139
C3—H3B···I2ii0.993.144.007 (2)147
C5—H5B···I1i0.993.114.067 (2)164
Symmetry codes: (i) x+1, y, z; (ii) x+1, y1, z.
(SDiazMesSI2_I2) top
Crystal data top
2(C23H30I2N2S)·2(I2)Z = 1
Mr = 1748.30F(000) = 820
Triclinic, P1Dx = 2.062 Mg m3
a = 8.3022 (9) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.3510 (11) ÅCell parameters from 71058 reflections
c = 15.5656 (16) Åθ = 2.2–30.1°
α = 83.691 (4)°µ = 4.51 mm1
β = 87.180 (4)°T = 100 K
γ = 75.024 (4)°Plank, red
V = 1408.1 (3) Å30.19 × 0.09 × 0.04 mm
Data collection top
Bruker D8 Venture Photon 2
diffractometer
7603 reflections with I > 2σ(I)
Radiation source: Incoatec IµSRint = 0.035
φ and ω scansθmax = 30.1°, θmin = 2.2°
Absorption correction: multi-scan
SADABS v2016/2 (Bruker AXS Inc., 2017)
h = 1111
Tmin = 0.579, Tmax = 0.746k = 1515
71058 measured reflectionsl = 2121
8260 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.017H-atom parameters constrained
wR(F2) = 0.039 w = 1/[σ2(Fo2) + (0.0082P)2 + 1.3172P]
where P = (Fo2 + 2Fc2)/3
S = 1.18(Δ/σ)max = 0.005
8260 reflectionsΔρmax = 0.50 e Å3
277 parametersΔρmin = 0.74 e Å3
0 restraints
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
I10.31247 (2)0.58104 (2)0.72662 (2)0.01485 (3)
I20.10499 (2)0.81980 (2)0.79506 (2)0.02312 (3)
S10.48485 (5)0.37844 (4)0.68562 (3)0.01452 (8)
N10.77284 (18)0.42648 (13)0.72581 (9)0.0121 (3)
N20.70824 (18)0.25045 (13)0.79742 (10)0.0124 (3)
C10.6709 (2)0.35257 (15)0.74190 (11)0.0120 (3)
C20.9150 (2)0.41687 (16)0.78278 (12)0.0145 (3)
H2A0.8795730.4016770.8437690.017*
H2B0.9470450.4955880.7761160.017*
C31.0651 (2)0.31443 (17)0.76182 (13)0.0172 (3)
H3A1.1508610.3036780.8060120.021*
H3B1.1138390.3370020.7050070.021*
C41.0164 (2)0.19328 (16)0.75944 (12)0.0158 (3)
H4A0.9788580.1893010.7006750.019*
H4B1.1159860.1242490.7712650.019*
C50.8792 (2)0.17845 (16)0.82443 (12)0.0158 (3)
H5A0.8804150.0905660.8341950.019*
H5B0.9034500.2041810.8801130.019*
C60.7473 (2)0.52375 (16)0.65478 (11)0.0132 (3)
C70.7003 (2)0.64546 (16)0.67572 (12)0.0150 (3)
C80.6790 (2)0.73859 (17)0.60760 (13)0.0178 (3)
H80.6468320.8214730.6204410.021*
C90.7031 (2)0.71437 (17)0.52180 (12)0.0184 (4)
C100.7531 (2)0.59230 (17)0.50401 (12)0.0173 (3)
H100.7720110.5747140.4455440.021*
C110.7763 (2)0.49498 (16)0.56929 (12)0.0147 (3)
C120.6723 (2)0.68036 (17)0.76724 (12)0.0183 (4)
H12A0.6524670.6109280.8057020.027*
H12B0.5751980.7507660.7695180.027*
H12C0.7711150.7020170.7858490.027*
C130.6764 (3)0.81838 (19)0.45019 (14)0.0286 (5)
H13A0.7741370.8522660.4446590.043*
H13B0.5773500.8826000.4638800.043*
H13C0.6604990.7877140.3956070.043*
C140.8295 (3)0.36548 (17)0.54486 (13)0.0201 (4)
H14A0.7335830.3296260.5500290.030*
H14B0.9170880.3166750.5835810.030*
H14C0.8724820.3659310.4850780.030*
C150.5758 (2)0.20126 (16)0.83975 (11)0.0124 (3)
C160.5412 (2)0.09825 (16)0.81058 (11)0.0132 (3)
C170.4238 (2)0.04684 (16)0.85725 (12)0.0156 (3)
H170.3982770.0228190.8381840.019*
C180.3431 (2)0.09504 (17)0.93107 (12)0.0155 (3)
C190.3811 (2)0.19780 (17)0.95803 (12)0.0164 (3)
H190.3263920.2314341.0081900.020*
C200.4973 (2)0.25261 (16)0.91329 (12)0.0149 (3)
C210.6261 (2)0.04315 (17)0.73114 (12)0.0179 (3)
H21A0.6519080.1078450.6899610.027*
H21B0.5519590.0038770.7042750.027*
H21C0.7295740.0180740.7475440.027*
C220.2200 (2)0.03633 (19)0.98208 (13)0.0204 (4)
H22A0.2776000.0219301.0288180.031*
H22B0.1702770.0070210.9438380.031*
H22C0.1320840.0998151.0067280.031*
C230.5348 (3)0.36361 (18)0.94498 (13)0.0209 (4)
H23A0.6539240.3459000.9568920.031*
H23B0.4695760.3836190.9980380.031*
H23C0.5051290.4333110.9005670.031*
I30.02911 (2)0.94288 (2)0.58243 (2)0.02671 (3)
I40.03703 (2)0.59671 (2)0.94795 (2)0.02033 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.01177 (5)0.01314 (5)0.01889 (6)0.00229 (4)0.00107 (4)0.00022 (4)
I20.02082 (6)0.01405 (6)0.03315 (7)0.00142 (5)0.00298 (5)0.00554 (5)
S10.01187 (18)0.01179 (18)0.0202 (2)0.00258 (15)0.00434 (15)0.00206 (15)
N10.0128 (7)0.0105 (6)0.0135 (7)0.0038 (5)0.0023 (5)0.0006 (5)
N20.0093 (6)0.0114 (6)0.0161 (7)0.0025 (5)0.0001 (5)0.0007 (5)
C10.0116 (7)0.0117 (7)0.0128 (7)0.0024 (6)0.0003 (6)0.0035 (6)
C20.0141 (8)0.0137 (8)0.0169 (8)0.0050 (6)0.0056 (6)0.0008 (6)
C30.0126 (8)0.0168 (8)0.0224 (9)0.0046 (6)0.0023 (7)0.0006 (7)
C40.0105 (7)0.0144 (8)0.0217 (9)0.0020 (6)0.0011 (6)0.0005 (7)
C50.0120 (8)0.0137 (8)0.0201 (9)0.0015 (6)0.0022 (6)0.0021 (6)
C60.0131 (8)0.0109 (7)0.0162 (8)0.0047 (6)0.0020 (6)0.0004 (6)
C70.0154 (8)0.0126 (8)0.0185 (8)0.0054 (6)0.0016 (6)0.0032 (6)
C80.0205 (9)0.0114 (8)0.0221 (9)0.0051 (7)0.0025 (7)0.0012 (7)
C90.0211 (9)0.0159 (8)0.0191 (9)0.0073 (7)0.0034 (7)0.0028 (7)
C100.0207 (9)0.0180 (9)0.0144 (8)0.0070 (7)0.0029 (7)0.0004 (7)
C110.0147 (8)0.0139 (8)0.0160 (8)0.0042 (6)0.0011 (6)0.0014 (6)
C120.0225 (9)0.0145 (8)0.0194 (9)0.0059 (7)0.0004 (7)0.0054 (7)
C130.0453 (13)0.0180 (9)0.0234 (10)0.0113 (9)0.0081 (9)0.0051 (8)
C140.0259 (10)0.0163 (9)0.0179 (9)0.0040 (7)0.0011 (7)0.0045 (7)
C150.0104 (7)0.0124 (7)0.0138 (8)0.0026 (6)0.0000 (6)0.0004 (6)
C160.0130 (8)0.0114 (7)0.0141 (8)0.0014 (6)0.0016 (6)0.0001 (6)
C170.0132 (8)0.0116 (8)0.0221 (9)0.0039 (6)0.0033 (7)0.0003 (6)
C180.0109 (8)0.0169 (8)0.0175 (8)0.0032 (6)0.0012 (6)0.0035 (6)
C190.0134 (8)0.0182 (8)0.0167 (8)0.0023 (7)0.0004 (6)0.0021 (7)
C200.0126 (8)0.0145 (8)0.0173 (8)0.0024 (6)0.0019 (6)0.0016 (6)
C210.0194 (9)0.0144 (8)0.0198 (9)0.0033 (7)0.0016 (7)0.0053 (7)
C220.0155 (8)0.0228 (9)0.0224 (9)0.0074 (7)0.0016 (7)0.0048 (7)
C230.0222 (9)0.0209 (9)0.0221 (9)0.0078 (7)0.0013 (7)0.0084 (7)
I30.03372 (8)0.02322 (7)0.02649 (7)0.01250 (6)0.00947 (5)0.00872 (5)
I40.01638 (6)0.02723 (7)0.01854 (6)0.00494 (5)0.00107 (4)0.00853 (5)
Geometric parameters (Å, º) top
I1—I23.0803 (3)C12—H12A0.9800
I1—S12.5053 (5)C12—H12B0.9800
S1—C11.7559 (18)C12—H12C0.9800
N1—C11.335 (2)C13—H13A0.9800
N1—C21.485 (2)C13—H13B0.9800
N1—C61.456 (2)C13—H13C0.9800
N2—C11.344 (2)C14—H14A0.9800
N2—C51.498 (2)C14—H14B0.9800
N2—C151.456 (2)C14—H14C0.9800
C2—H2A0.9900C15—C161.400 (2)
C2—H2B0.9900C15—C201.397 (2)
C2—C31.519 (3)C16—C171.396 (2)
C3—H3A0.9900C16—C211.508 (2)
C3—H3B0.9900C17—H170.9500
C3—C41.535 (3)C17—C181.393 (3)
C4—H4A0.9900C18—C191.395 (3)
C4—H4B0.9900C18—C221.509 (2)
C4—C51.516 (3)C19—H190.9500
C5—H5A0.9900C19—C201.397 (2)
C5—H5B0.9900C20—C231.510 (3)
C6—C71.405 (2)C21—H21A0.9800
C6—C111.400 (2)C21—H21B0.9800
C7—C81.396 (3)C21—H21C0.9800
C7—C121.511 (3)C22—H22A0.9800
C8—H80.9500C22—H22B0.9800
C8—C91.388 (3)C22—H22C0.9800
C9—C101.394 (3)C23—H23A0.9800
C9—C131.512 (3)C23—H23B0.9800
C10—H100.9500C23—H23C0.9800
C10—C111.397 (2)I3—I3i2.7507 (4)
C11—C141.507 (3)I4—I4ii2.7645 (3)
S1—I1—I2174.564 (12)C7—C12—H12B109.5
C1—S1—I1104.65 (6)C7—C12—H12C109.5
C1—N1—C2121.09 (14)H12A—C12—H12B109.5
C1—N1—C6122.46 (15)H12A—C12—H12C109.5
C6—N1—C2116.39 (13)H12B—C12—H12C109.5
C1—N2—C5126.41 (14)C9—C13—H13A109.5
C1—N2—C15120.30 (14)C9—C13—H13B109.5
C15—N2—C5113.27 (13)C9—C13—H13C109.5
N1—C1—S1121.32 (13)H13A—C13—H13B109.5
N1—C1—N2122.70 (16)H13A—C13—H13C109.5
N2—C1—S1115.85 (12)H13B—C13—H13C109.5
N1—C2—H2A109.2C11—C14—H14A109.5
N1—C2—H2B109.2C11—C14—H14B109.5
N1—C2—C3111.99 (15)C11—C14—H14C109.5
H2A—C2—H2B107.9H14A—C14—H14B109.5
C3—C2—H2A109.2H14A—C14—H14C109.5
C3—C2—H2B109.2H14B—C14—H14C109.5
C2—C3—H3A109.4C16—C15—N2119.45 (15)
C2—C3—H3B109.4C20—C15—N2118.26 (15)
C2—C3—C4111.23 (15)C20—C15—C16122.05 (16)
H3A—C3—H3B108.0C15—C16—C21121.90 (16)
C4—C3—H3A109.4C17—C16—C15118.02 (16)
C4—C3—H3B109.4C17—C16—C21120.08 (16)
C3—C4—H4A109.0C16—C17—H17119.1
C3—C4—H4B109.0C18—C17—C16121.70 (17)
H4A—C4—H4B107.8C18—C17—H17119.1
C5—C4—C3112.93 (16)C17—C18—C19118.53 (16)
C5—C4—H4A109.0C17—C18—C22121.01 (17)
C5—C4—H4B109.0C19—C18—C22120.45 (17)
N2—C5—C4114.08 (14)C18—C19—H19119.1
N2—C5—H5A108.7C18—C19—C20121.81 (17)
N2—C5—H5B108.7C20—C19—H19119.1
C4—C5—H5A108.7C15—C20—C19117.88 (16)
C4—C5—H5B108.7C15—C20—C23122.14 (16)
H5A—C5—H5B107.6C19—C20—C23119.98 (17)
C7—C6—N1117.67 (15)C16—C21—H21A109.5
C11—C6—N1120.20 (15)C16—C21—H21B109.5
C11—C6—C7122.07 (16)C16—C21—H21C109.5
C6—C7—C12123.71 (16)H21A—C21—H21B109.5
C8—C7—C6117.60 (17)H21A—C21—H21C109.5
C8—C7—C12118.70 (16)H21B—C21—H21C109.5
C7—C8—H8118.8C18—C22—H22A109.5
C9—C8—C7122.31 (17)C18—C22—H22B109.5
C9—C8—H8118.8C18—C22—H22C109.5
C8—C9—C10118.20 (17)H22A—C22—H22B109.5
C8—C9—C13120.37 (18)H22A—C22—H22C109.5
C10—C9—C13121.43 (18)H22B—C22—H22C109.5
C9—C10—H10118.9C20—C23—H23A109.5
C9—C10—C11122.22 (17)C20—C23—H23B109.5
C11—C10—H10118.9C20—C23—H23C109.5
C6—C11—C14123.33 (16)H23A—C23—H23B109.5
C10—C11—C6117.58 (16)H23A—C23—H23C109.5
C10—C11—C14119.09 (16)H23B—C23—H23C109.5
C7—C12—H12A109.5
I1—S1—C1—N163.56 (15)C6—N1—C2—C3101.40 (17)
I1—S1—C1—N2120.48 (12)C6—C7—C8—C90.3 (3)
N1—C2—C3—C451.4 (2)C7—C6—C11—C101.5 (3)
N1—C6—C7—C8178.79 (16)C7—C6—C11—C14178.94 (17)
N1—C6—C7—C121.1 (3)C7—C8—C9—C101.1 (3)
N1—C6—C11—C10178.63 (16)C7—C8—C9—C13179.24 (19)
N1—C6—C11—C141.8 (3)C8—C9—C10—C111.2 (3)
N2—C15—C16—C17174.43 (15)C9—C10—C11—C60.1 (3)
N2—C15—C16—C215.8 (3)C9—C10—C11—C14179.67 (18)
N2—C15—C20—C19174.33 (16)C11—C6—C7—C81.6 (3)
N2—C15—C20—C235.5 (3)C11—C6—C7—C12178.32 (17)
C1—N1—C2—C381.3 (2)C12—C7—C8—C9179.64 (18)
C1—N1—C6—C7111.24 (19)C13—C9—C10—C11179.15 (19)
C1—N1—C6—C1171.5 (2)C15—N2—C1—S129.4 (2)
C1—N2—C5—C424.7 (2)C15—N2—C1—N1154.74 (16)
C1—N2—C15—C16103.38 (19)C15—N2—C5—C4156.97 (15)
C1—N2—C15—C2082.1 (2)C15—C16—C17—C180.4 (3)
C2—N1—C1—S1169.88 (13)C16—C15—C20—C190.0 (3)
C2—N1—C1—N214.4 (3)C16—C15—C20—C23179.88 (17)
C2—N1—C6—C766.0 (2)C16—C17—C18—C190.4 (3)
C2—N1—C6—C11111.30 (18)C16—C17—C18—C22178.36 (17)
C2—C3—C4—C534.2 (2)C17—C18—C19—C200.2 (3)
C3—C4—C5—N277.8 (2)C18—C19—C20—C150.0 (3)
C5—N2—C1—S1152.39 (14)C18—C19—C20—C23179.86 (17)
C5—N2—C1—N123.5 (3)C20—C15—C16—C170.1 (3)
C5—N2—C15—C1678.2 (2)C20—C15—C16—C21179.95 (17)
C5—N2—C15—C2096.35 (19)C21—C16—C17—C18179.84 (17)
C6—N1—C1—S17.2 (2)C22—C18—C19—C20178.55 (17)
C6—N1—C1—N2168.47 (16)
Symmetry codes: (i) x, y+2, z+1; (ii) x, y+1, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2B···I4iii0.993.223.7794 (18)118
C5—H5A···I2iv0.993.264.0837 (19)142
Symmetry codes: (iii) x+1, y, z; (iv) x+1, y1, z.
(SDiazMesSeI_I3) top
Crystal data top
C23H30IN2Se·I3F(000) = 1712
Mr = 921.05Dx = 2.183 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 11.0063 (7) ÅCell parameters from 9954 reflections
b = 22.9632 (14) Åθ = 2.5–27.5°
c = 11.1015 (6) ŵ = 5.76 mm1
β = 93.024 (2)°T = 100 K
V = 2801.9 (3) Å3Plate, red
Z = 40.06 × 0.06 × 0.02 mm
Data collection top
Bruker D8 Venture Photon 2
diffractometer
5536 reflections with I > 2σ(I)
Radiation source: Incoatec IµSRint = 0.091
φ and ω scansθmax = 27.5°, θmin = 2.1°
Absorption correction: multi-scan
SADABS v2016/2 (Bruker AXS Inc., 2017)
h = 1214
Tmin = 0.606, Tmax = 0.746k = 2929
36709 measured reflectionsl = 1314
6428 independent reflections
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.062Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127H-atom parameters constrained
S = 1.17 w = 1/[σ2(Fo2) + (0.0131P)2 + 65.9822P]
where P = (Fo2 + 2Fc2)/3
6428 reflections(Δ/σ)max = 0.001
278 parametersΔρmax = 2.17 e Å3
30 restraintsΔρmin = 1.40 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.

Refinement. Refined as a 2-component twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
I10.59561 (6)0.64902 (3)0.81087 (6)0.01566 (15)
Se10.40931 (11)0.71085 (5)0.86165 (11)0.0219 (3)
N10.2695 (8)0.6471 (4)0.6789 (7)0.0128 (17)
N20.2234 (8)0.7464 (4)0.7042 (8)0.0134 (17)
C10.2883 (9)0.6986 (4)0.7330 (9)0.0106 (19)
C20.2029 (10)0.6450 (5)0.5580 (9)0.020 (2)
H2A0.2268020.6092810.5152780.024*
H2B0.2273650.6788950.5097380.024*
C30.0654 (10)0.6455 (5)0.5662 (10)0.019 (2)
H3A0.0266280.6477270.4837960.023*
H3B0.0395050.6086540.6031490.023*
C40.0220 (10)0.6962 (4)0.6399 (9)0.014 (2)
H4A0.0201300.6841140.7253810.017*
H4B0.0621120.7063800.6115000.017*
C50.1018 (10)0.7498 (5)0.6320 (10)0.019 (2)
H5A0.0561920.7838710.6604970.022*
H5B0.1178010.7566590.5462260.022*
C60.3091 (10)0.5925 (4)0.7319 (9)0.0133 (17)
C70.3935 (9)0.5589 (4)0.6712 (9)0.0128 (16)
C80.4292 (10)0.5065 (4)0.7216 (9)0.0141 (18)
H80.4861850.4832880.6817130.017*
C90.3842 (10)0.4860 (5)0.8301 (10)0.017 (2)
C100.2992 (10)0.5200 (5)0.8848 (9)0.017 (2)
H100.2665420.5063030.9570840.021*
C110.2594 (9)0.5735 (4)0.8382 (9)0.013 (2)
C120.4501 (10)0.5785 (5)0.5575 (10)0.018 (2)
H12A0.5363700.5677310.5611450.028*
H12B0.4423530.6208510.5496160.028*
H12C0.4083920.5596170.4877800.028*
C130.4292 (11)0.4289 (5)0.8833 (11)0.025 (3)
H13A0.4969640.4362120.9422090.037*
H13B0.4569300.4037650.8188500.037*
H13C0.3629570.4095600.9233920.037*
C140.1644 (11)0.6067 (5)0.9025 (10)0.021 (2)
H14A0.1252400.5806670.9587050.032*
H14B0.1031640.6218650.8433540.032*
H14C0.2029410.6391290.9473000.032*
C150.2641 (9)0.8031 (4)0.7498 (9)0.013 (2)
C160.3472 (9)0.8346 (4)0.6817 (9)0.013 (2)
C170.3851 (10)0.8889 (5)0.7275 (10)0.0174 (18)
H170.4409070.9113770.6844100.021*
C180.3424 (10)0.9111 (5)0.8364 (10)0.0177 (14)
C190.2600 (10)0.8784 (5)0.8961 (10)0.0168 (18)
H190.2291780.8938850.9676950.020*
C200.2194 (10)0.8242 (5)0.8575 (10)0.017 (2)
C210.3973 (11)0.8098 (5)0.5704 (10)0.023 (2)
H21A0.4610630.7814800.5929380.034*
H21B0.4318150.8412350.5231070.034*
H21C0.3320250.7905250.5220820.034*
C220.3888 (10)0.9692 (4)0.8813 (10)0.0178 (15)
H22A0.4775670.9703190.8785060.027*
H22B0.3658730.9750120.9646300.027*
H22C0.3530121.0002160.8301640.027*
C230.1302 (10)0.7901 (5)0.9276 (10)0.021 (2)
H23A0.0492950.7924810.8866320.031*
H23B0.1272910.8063671.0090020.031*
H23C0.1559770.7492980.9327880.031*
I20.82187 (7)0.56569 (3)0.76383 (8)0.02662 (19)
I30.76938 (6)0.43650 (3)0.76074 (6)0.01781 (16)
I40.73525 (8)0.31356 (3)0.76667 (7)0.02759 (19)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.0164 (3)0.0133 (3)0.0168 (3)0.0016 (3)0.0037 (2)0.0004 (3)
Se10.0208 (6)0.0211 (6)0.0225 (6)0.0077 (5)0.0115 (5)0.0126 (4)
N10.018 (4)0.008 (4)0.012 (4)0.001 (3)0.003 (3)0.004 (3)
N20.014 (4)0.007 (4)0.018 (4)0.001 (3)0.005 (3)0.002 (3)
C10.006 (4)0.013 (5)0.013 (5)0.002 (4)0.004 (4)0.001 (4)
C20.025 (6)0.022 (6)0.013 (5)0.009 (5)0.002 (4)0.006 (4)
C30.025 (6)0.013 (5)0.019 (5)0.004 (4)0.005 (5)0.005 (4)
C40.019 (5)0.009 (5)0.014 (5)0.005 (4)0.006 (4)0.000 (4)
C50.017 (5)0.017 (5)0.021 (5)0.000 (4)0.003 (4)0.002 (4)
C60.014 (4)0.012 (4)0.014 (4)0.000 (3)0.004 (3)0.003 (3)
C70.013 (3)0.011 (3)0.015 (3)0.000 (3)0.002 (3)0.006 (3)
C80.014 (4)0.014 (4)0.015 (4)0.003 (3)0.001 (3)0.006 (3)
C90.022 (6)0.012 (5)0.017 (5)0.007 (4)0.005 (4)0.005 (4)
C100.018 (5)0.021 (6)0.013 (5)0.007 (4)0.002 (4)0.003 (4)
C110.012 (5)0.015 (5)0.011 (5)0.000 (4)0.005 (4)0.001 (4)
C120.017 (5)0.019 (6)0.019 (5)0.007 (4)0.007 (4)0.003 (4)
C130.019 (6)0.026 (6)0.029 (6)0.003 (5)0.010 (5)0.003 (5)
C140.024 (6)0.027 (6)0.012 (5)0.010 (5)0.006 (4)0.005 (4)
C150.012 (5)0.006 (5)0.021 (5)0.002 (4)0.008 (4)0.002 (4)
C160.015 (5)0.014 (5)0.011 (5)0.001 (4)0.003 (4)0.004 (4)
C170.012 (4)0.014 (4)0.026 (4)0.002 (3)0.005 (3)0.000 (3)
C180.014 (3)0.012 (3)0.026 (3)0.001 (3)0.008 (3)0.003 (3)
C190.017 (4)0.013 (4)0.020 (4)0.000 (3)0.006 (3)0.002 (3)
C200.012 (5)0.012 (5)0.027 (6)0.003 (4)0.004 (4)0.004 (4)
C210.022 (6)0.024 (6)0.023 (6)0.003 (5)0.009 (5)0.001 (5)
C220.014 (3)0.012 (3)0.027 (3)0.002 (3)0.008 (3)0.003 (3)
C230.023 (6)0.014 (5)0.026 (6)0.000 (4)0.007 (5)0.003 (4)
I20.0221 (4)0.0214 (4)0.0370 (5)0.0032 (3)0.0071 (3)0.0011 (3)
I30.0159 (3)0.0253 (4)0.0121 (3)0.0018 (3)0.0008 (2)0.0001 (3)
I40.0392 (5)0.0260 (4)0.0174 (4)0.0077 (3)0.0001 (3)0.0027 (3)
Geometric parameters (Å, º) top
I1—Se12.5806 (13)C12—H12B0.9800
Se1—C11.921 (10)C12—H12C0.9800
N1—C11.339 (13)C13—H13A0.9800
N1—C21.496 (13)C13—H13B0.9800
N1—C61.441 (13)C13—H13C0.9800
N2—C11.339 (13)C14—H14A0.9800
N2—C51.526 (13)C14—H14B0.9800
N2—C151.458 (12)C14—H14C0.9800
C2—H2A0.9900C15—C161.416 (15)
C2—H2B0.9900C15—C201.402 (16)
C2—C31.521 (16)C16—C171.402 (14)
C3—H3A0.9900C16—C211.492 (14)
C3—H3B0.9900C17—H170.9500
C3—C41.515 (15)C17—C181.415 (16)
C4—H4A0.9900C18—C191.374 (16)
C4—H4B0.9900C18—C221.505 (14)
C4—C51.517 (14)C19—H190.9500
C5—H5A0.9900C19—C201.383 (15)
C5—H5B0.9900C20—C231.504 (15)
C6—C71.407 (14)C21—H21A0.9800
C6—C111.398 (15)C21—H21B0.9800
C7—C81.377 (14)C21—H21C0.9800
C7—C121.505 (14)C22—H22A0.9800
C8—H80.9500C22—H22B0.9800
C8—C91.407 (15)C22—H22C0.9800
C9—C101.383 (16)C23—H23A0.9800
C9—C131.512 (16)C23—H23B0.9800
C10—H100.9500C23—H23C0.9800
C10—C111.394 (15)I2—I33.0222 (11)
C11—C141.503 (14)I3—I42.8492 (11)
C12—H12A0.9800
C1—Se1—I1106.5 (3)C7—C12—H12C109.5
C1—N1—C2119.2 (8)H12A—C12—H12B109.5
C1—N1—C6123.3 (8)H12A—C12—H12C109.5
C6—N1—C2117.5 (8)H12B—C12—H12C109.5
C1—N2—C5127.5 (9)C9—C13—H13A109.5
C1—N2—C15119.9 (8)C9—C13—H13B109.5
C15—N2—C5112.4 (8)C9—C13—H13C109.5
N1—C1—Se1123.2 (7)H13A—C13—H13B109.5
N2—C1—Se1113.4 (7)H13A—C13—H13C109.5
N2—C1—N1123.4 (9)H13B—C13—H13C109.5
N1—C2—H2A109.0C11—C14—H14A109.5
N1—C2—H2B109.0C11—C14—H14B109.5
N1—C2—C3112.9 (9)C11—C14—H14C109.5
H2A—C2—H2B107.8H14A—C14—H14B109.5
C3—C2—H2A109.0H14A—C14—H14C109.5
C3—C2—H2B109.0H14B—C14—H14C109.5
C2—C3—H3A109.1C16—C15—N2117.8 (9)
C2—C3—H3B109.1C20—C15—N2119.2 (9)
H3A—C3—H3B107.8C20—C15—C16123.0 (9)
C4—C3—C2112.5 (9)C15—C16—C21121.6 (9)
C4—C3—H3A109.1C17—C16—C15116.7 (9)
C4—C3—H3B109.1C17—C16—C21121.6 (10)
C3—C4—H4A109.0C16—C17—H17119.2
C3—C4—H4B109.0C16—C17—C18121.6 (10)
C3—C4—C5113.1 (9)C18—C17—H17119.2
H4A—C4—H4B107.8C17—C18—C22118.7 (10)
C5—C4—H4A109.0C19—C18—C17118.2 (10)
C5—C4—H4B109.0C19—C18—C22123.1 (10)
N2—C5—H5A108.5C18—C19—H19118.2
N2—C5—H5B108.5C18—C19—C20123.6 (11)
C4—C5—N2115.0 (9)C20—C19—H19118.2
C4—C5—H5A108.5C15—C20—C23122.0 (9)
C4—C5—H5B108.5C19—C20—C15116.9 (10)
H5A—C5—H5B107.5C19—C20—C23121.1 (10)
C7—C6—N1118.3 (9)C16—C21—H21A109.5
C11—C6—N1119.6 (9)C16—C21—H21B109.5
C11—C6—C7122.1 (9)C16—C21—H21C109.5
C6—C7—C12123.5 (9)H21A—C21—H21B109.5
C8—C7—C6117.8 (10)H21A—C21—H21C109.5
C8—C7—C12118.7 (9)H21B—C21—H21C109.5
C7—C8—H8118.9C18—C22—H22A109.5
C7—C8—C9122.3 (10)C18—C22—H22B109.5
C9—C8—H8118.9C18—C22—H22C109.5
C8—C9—C13120.1 (10)H22A—C22—H22B109.5
C10—C9—C8117.7 (10)H22A—C22—H22C109.5
C10—C9—C13122.2 (10)H22B—C22—H22C109.5
C9—C10—H10118.6C20—C23—H23A109.5
C9—C10—C11122.8 (10)C20—C23—H23B109.5
C11—C10—H10118.6C20—C23—H23C109.5
C6—C11—C14123.7 (9)H23A—C23—H23B109.5
C10—C11—C6117.3 (10)H23A—C23—H23C109.5
C10—C11—C14118.9 (9)H23B—C23—H23C109.5
C7—C12—H12A109.5I4—I3—I2176.12 (4)
C7—C12—H12B109.5
N1—C2—C3—C453.7 (12)C6—C7—C8—C90.0 (15)
N1—C6—C7—C8179.0 (9)C7—C6—C11—C101.7 (15)
N1—C6—C7—C123.6 (15)C7—C6—C11—C14176.9 (10)
N1—C6—C11—C10179.0 (9)C7—C8—C9—C101.5 (15)
N1—C6—C11—C140.4 (15)C7—C8—C9—C13178.2 (9)
N2—C15—C16—C17179.9 (9)C8—C9—C10—C111.5 (15)
N2—C15—C16—C213.3 (15)C9—C10—C11—C60.1 (15)
N2—C15—C20—C19179.4 (9)C9—C10—C11—C14178.6 (10)
N2—C15—C20—C230.2 (15)C11—C6—C7—C81.7 (15)
C1—N1—C2—C383.4 (12)C11—C6—C7—C12179.1 (10)
C1—N1—C6—C7118.3 (11)C12—C7—C8—C9177.6 (10)
C1—N1—C6—C1164.3 (13)C13—C9—C10—C11178.3 (9)
C1—N2—C5—C428.2 (15)C15—N2—C1—Se113.1 (12)
C1—N2—C15—C1687.2 (12)C15—N2—C1—N1168.0 (9)
C1—N2—C15—C2093.2 (12)C15—N2—C5—C4148.0 (9)
C2—N1—C1—Se1161.4 (7)C15—C16—C17—C180.1 (15)
C2—N1—C1—N219.7 (15)C16—C15—C20—C190.2 (15)
C2—N1—C6—C762.5 (12)C16—C15—C20—C23179.4 (10)
C2—N1—C6—C11114.9 (11)C16—C17—C18—C191.2 (16)
C2—C3—C4—C531.2 (12)C16—C17—C18—C22178.9 (9)
C3—C4—C5—N275.1 (11)C17—C18—C19—C202.1 (16)
C5—N2—C1—Se1162.9 (8)C18—C19—C20—C151.6 (16)
C5—N2—C1—N116.0 (16)C18—C19—C20—C23179.2 (10)
C5—N2—C15—C1696.2 (11)C20—C15—C16—C170.6 (15)
C5—N2—C15—C2083.3 (11)C20—C15—C16—C21177.2 (10)
C6—N1—C1—Se119.4 (14)C21—C16—C17—C18176.6 (10)
C6—N1—C1—N2159.4 (10)C22—C18—C19—C20178.1 (10)
C6—N1—C2—C395.8 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2A···I3i0.993.244.029 (10)138
C2—H2B···I4i0.993.123.823 (11)129
C3—H3B···I2ii0.993.223.998 (11)137
C5—H5B···Se1iii0.993.093.693 (11)121
Symmetry codes: (i) x+1, y+1, z+1; (ii) x1, y, z; (iii) x1/2, y+3/2, z1/2.
(SDiazMesSeI_I3_DCM) top
Crystal data top
C23H30IN2Se·I3·CH2Cl2Z = 2
Mr = 1005.97F(000) = 940
Triclinic, P1Dx = 2.129 Mg m3
a = 8.4541 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.5353 (4) ÅCell parameters from 64752 reflections
c = 22.0045 (11) Åθ = 2.4–29.6°
α = 93.258 (2)°µ = 5.32 mm1
β = 90.198 (2)°T = 100 K
γ = 98.032 (2)°Plate, red
V = 1569.58 (13) Å30.24 × 0.15 × 0.05 mm
Data collection top
Bruker D8 Venture Photon 2
diffractometer
7994 reflections with I > 2σ(I)
Radiation source: Incoatec IµSRint = 0.038
φ and ω scansθmax = 29.6°, θmin = 2.4°
Absorption correction: multi-scan
SADABS v2016/2 (Bruker AXS Inc., 2017)
h = 1111
Tmin = 0.527, Tmax = 0.746k = 1111
64752 measured reflectionsl = 3030
8821 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.019H-atom parameters constrained
wR(F2) = 0.043 w = 1/[σ2(Fo2) + (0.0077P)2 + 1.7629P]
where P = (Fo2 + 2Fc2)/3
S = 1.13(Δ/σ)max = 0.004
8821 reflectionsΔρmax = 0.81 e Å3
304 parametersΔρmin = 0.88 e Å3
0 restraints
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
I11.08899 (2)0.41978 (2)0.70459 (2)0.01695 (3)
I21.21875 (2)0.08963 (2)0.67867 (2)0.02237 (4)
I31.31997 (2)0.08657 (2)0.80982 (2)0.01745 (3)
I41.42535 (2)0.08034 (2)0.93236 (2)0.02692 (4)
Se10.99525 (2)0.69370 (2)0.72771 (2)0.01595 (4)
N10.7724 (2)0.54815 (19)0.81139 (8)0.0131 (3)
N20.6632 (2)0.6679 (2)0.73064 (8)0.0150 (3)
C10.7875 (2)0.6272 (2)0.76082 (9)0.0133 (4)
C20.6158 (2)0.4582 (2)0.82727 (10)0.0166 (4)
H2A0.6344510.3732520.8541540.020*
H2B0.5626330.4071490.7896110.020*
C30.5060 (3)0.5616 (3)0.85889 (11)0.0220 (4)
H3A0.5503200.5985570.8997400.026*
H3B0.4001360.4983990.8643060.026*
C40.4862 (3)0.7049 (3)0.82250 (11)0.0225 (5)
H4A0.3810500.7383250.8318900.027*
H4B0.5696190.7936030.8357720.027*
C50.4974 (3)0.6740 (3)0.75456 (10)0.0207 (4)
H5A0.4306540.5718240.7428820.025*
H5B0.4511810.7579660.7342350.025*
C60.9038 (2)0.5457 (2)0.85400 (9)0.0135 (4)
C70.9539 (2)0.3996 (2)0.86445 (9)0.0135 (4)
C81.0733 (2)0.3973 (2)0.90838 (9)0.0151 (4)
H81.1089850.2993230.9158700.018*
C91.1414 (2)0.5337 (3)0.94140 (9)0.0161 (4)
C101.0874 (3)0.6762 (3)0.93010 (10)0.0178 (4)
H101.1337940.7702830.9522790.021*
C110.9675 (3)0.6854 (2)0.88728 (9)0.0162 (4)
C120.8835 (3)0.2452 (2)0.83186 (10)0.0168 (4)
H12A0.8071450.1859520.8584730.025*
H12B0.9690920.1824520.8212940.025*
H12C0.8284540.2669710.7946380.025*
C131.2663 (3)0.5267 (3)0.98998 (10)0.0217 (4)
H13A1.2143260.5130261.0294430.032*
H13B1.3413330.6253720.9919580.032*
H13C1.3243370.4370120.9800850.032*
C140.9079 (3)0.8425 (3)0.88093 (11)0.0229 (5)
H14A0.9090020.8669890.8379460.034*
H14B0.9774240.9258850.9044970.034*
H14C0.7986130.8364350.8962120.034*
C150.6763 (2)0.7079 (2)0.66740 (9)0.0147 (4)
C160.6542 (3)0.5839 (3)0.62244 (10)0.0178 (4)
C170.6543 (3)0.6254 (3)0.56198 (10)0.0233 (5)
H170.6420230.5438070.5304080.028*
C180.6719 (3)0.7830 (3)0.54662 (10)0.0241 (5)
C190.6949 (3)0.9021 (3)0.59294 (10)0.0213 (4)
H190.7093951.0097040.5826740.026*
C200.6971 (2)0.8674 (2)0.65402 (10)0.0162 (4)
C210.6309 (3)0.4128 (3)0.63782 (11)0.0247 (5)
H21A0.7149280.3948420.6663330.037*
H21B0.6362700.3452590.6005600.037*
H21C0.5262280.3867960.6565790.037*
C220.6606 (4)0.8253 (4)0.48136 (12)0.0380 (6)
H22A0.5542140.8531820.4733410.057*
H22B0.6785320.7343680.4543060.057*
H22C0.7417320.9157690.4739720.057*
C230.7241 (3)0.9986 (3)0.70328 (10)0.0214 (4)
H23A0.6283020.9969650.7283250.032*
H23B0.7463311.1009330.6846900.032*
H23C0.8151830.9833550.7288650.032*
Cl10.27587 (8)0.70192 (9)0.57406 (3)0.03720 (15)
Cl20.04931 (9)0.71889 (11)0.47552 (3)0.04679 (18)
C240.0769 (3)0.7172 (4)0.55546 (13)0.0365 (6)
H24A0.0470930.8159220.5752140.044*
H24B0.0058710.6266100.5711560.044*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.01424 (6)0.02080 (7)0.01537 (6)0.00052 (5)0.00161 (5)0.00211 (5)
I20.03007 (8)0.01919 (7)0.01743 (7)0.00196 (6)0.00370 (6)0.00084 (5)
I30.01655 (6)0.01388 (6)0.02183 (7)0.00186 (5)0.00191 (5)0.00082 (5)
I40.03274 (8)0.02312 (7)0.02366 (8)0.00002 (6)0.00650 (6)0.00070 (6)
Se10.01255 (9)0.01629 (9)0.01856 (10)0.00137 (7)0.00119 (7)0.00550 (8)
N10.0109 (7)0.0130 (7)0.0153 (8)0.0003 (6)0.0018 (6)0.0036 (6)
N20.0137 (8)0.0168 (8)0.0147 (8)0.0021 (6)0.0011 (6)0.0029 (6)
C10.0133 (9)0.0105 (8)0.0154 (9)0.0001 (7)0.0006 (7)0.0002 (7)
C20.0141 (9)0.0153 (9)0.0203 (10)0.0008 (7)0.0031 (8)0.0067 (8)
C30.0182 (10)0.0271 (11)0.0221 (11)0.0058 (9)0.0064 (8)0.0072 (9)
C40.0207 (11)0.0252 (11)0.0239 (11)0.0092 (9)0.0065 (9)0.0052 (9)
C50.0148 (10)0.0245 (11)0.0244 (11)0.0071 (8)0.0013 (8)0.0051 (9)
C60.0138 (9)0.0150 (9)0.0115 (9)0.0006 (7)0.0013 (7)0.0025 (7)
C70.0152 (9)0.0146 (9)0.0110 (9)0.0020 (7)0.0027 (7)0.0021 (7)
C80.0150 (9)0.0180 (9)0.0133 (9)0.0049 (7)0.0005 (7)0.0032 (7)
C90.0129 (9)0.0237 (10)0.0112 (9)0.0009 (8)0.0028 (7)0.0023 (8)
C100.0172 (10)0.0180 (10)0.0167 (10)0.0016 (8)0.0010 (8)0.0023 (8)
C110.0188 (10)0.0146 (9)0.0152 (10)0.0009 (8)0.0016 (8)0.0029 (7)
C120.0181 (10)0.0140 (9)0.0179 (10)0.0016 (7)0.0002 (8)0.0014 (7)
C130.0163 (10)0.0343 (12)0.0139 (10)0.0019 (9)0.0015 (8)0.0013 (9)
C140.0299 (12)0.0147 (10)0.0239 (11)0.0034 (9)0.0033 (9)0.0006 (8)
C150.0142 (9)0.0175 (9)0.0125 (9)0.0016 (7)0.0015 (7)0.0029 (7)
C160.0156 (9)0.0185 (10)0.0184 (10)0.0004 (8)0.0034 (8)0.0014 (8)
C170.0216 (11)0.0300 (12)0.0173 (11)0.0031 (9)0.0045 (8)0.0045 (9)
C180.0214 (11)0.0350 (13)0.0161 (10)0.0032 (9)0.0026 (8)0.0052 (9)
C190.0218 (11)0.0233 (11)0.0195 (11)0.0034 (9)0.0008 (8)0.0083 (8)
C200.0139 (9)0.0188 (10)0.0160 (10)0.0029 (7)0.0015 (7)0.0015 (8)
C210.0263 (12)0.0178 (10)0.0289 (12)0.0006 (9)0.0035 (10)0.0019 (9)
C220.0455 (16)0.0535 (18)0.0165 (12)0.0089 (14)0.0040 (11)0.0094 (11)
C230.0262 (11)0.0163 (10)0.0219 (11)0.0039 (8)0.0009 (9)0.0009 (8)
Cl10.0272 (3)0.0408 (4)0.0424 (4)0.0028 (3)0.0020 (3)0.0040 (3)
Cl20.0392 (4)0.0684 (5)0.0305 (4)0.0015 (4)0.0049 (3)0.0049 (3)
C240.0232 (12)0.0535 (17)0.0302 (14)0.0007 (12)0.0038 (10)0.0056 (12)
Geometric parameters (Å, º) top
I1—Se12.5959 (3)C12—H12B0.9800
I2—I33.0098 (2)C12—H12C0.9800
I3—I42.8428 (2)C13—H13A0.9800
Se1—C11.928 (2)C13—H13B0.9800
N1—C11.331 (3)C13—H13C0.9800
N1—C21.488 (3)C14—H14A0.9800
N1—C61.454 (3)C14—H14B0.9800
N2—C11.338 (3)C14—H14C0.9800
N2—C51.506 (3)C15—C161.399 (3)
N2—C151.453 (3)C15—C201.396 (3)
C2—H2A0.9900C16—C171.396 (3)
C2—H2B0.9900C16—C211.505 (3)
C2—C31.513 (3)C17—H170.9500
C3—H3A0.9900C17—C181.394 (3)
C3—H3B0.9900C18—C191.391 (3)
C3—C41.527 (3)C18—C221.506 (3)
C4—H4A0.9900C19—H190.9500
C4—H4B0.9900C19—C201.393 (3)
C4—C51.509 (3)C20—C231.507 (3)
C5—H5A0.9900C21—H21A0.9800
C5—H5B0.9900C21—H21B0.9800
C6—C71.402 (3)C21—H21C0.9800
C6—C111.402 (3)C22—H22A0.9800
C7—C81.399 (3)C22—H22B0.9800
C7—C121.508 (3)C22—H22C0.9800
C8—H80.9500C23—H23A0.9800
C8—C91.389 (3)C23—H23B0.9800
C9—C101.392 (3)C23—H23C0.9800
C9—C131.510 (3)Cl1—C241.754 (3)
C10—H100.9500Cl2—C241.775 (3)
C10—C111.395 (3)C24—H24A0.9900
C11—C141.510 (3)C24—H24B0.9900
C12—H12A0.9800
I4—I3—I2178.081 (7)H12A—C12—H12C109.5
C1—Se1—I1100.02 (6)H12B—C12—H12C109.5
C1—N1—C2120.48 (17)C9—C13—H13A109.5
C1—N1—C6122.97 (17)C9—C13—H13B109.5
C6—N1—C2116.54 (16)C9—C13—H13C109.5
C1—N2—C5126.83 (18)H13A—C13—H13B109.5
C1—N2—C15121.19 (17)H13A—C13—H13C109.5
C15—N2—C5111.95 (16)H13B—C13—H13C109.5
N1—C1—Se1120.79 (14)C11—C14—H14A109.5
N1—C1—N2123.24 (18)C11—C14—H14B109.5
N2—C1—Se1115.96 (15)C11—C14—H14C109.5
N1—C2—H2A109.0H14A—C14—H14B109.5
N1—C2—H2B109.0H14A—C14—H14C109.5
N1—C2—C3112.86 (17)H14B—C14—H14C109.5
H2A—C2—H2B107.8C16—C15—N2118.03 (18)
C3—C2—H2A109.0C20—C15—N2118.86 (18)
C3—C2—H2B109.0C20—C15—C16122.89 (19)
C2—C3—H3A109.3C15—C16—C21122.1 (2)
C2—C3—H3B109.3C17—C16—C15117.1 (2)
C2—C3—C4111.52 (18)C17—C16—C21120.8 (2)
H3A—C3—H3B108.0C16—C17—H17119.1
C4—C3—H3A109.3C18—C17—C16121.9 (2)
C4—C3—H3B109.3C18—C17—H17119.1
C3—C4—H4A108.8C17—C18—C22121.1 (2)
C3—C4—H4B108.8C19—C18—C17118.8 (2)
H4A—C4—H4B107.7C19—C18—C22120.0 (2)
C5—C4—C3113.74 (19)C18—C19—H19119.2
C5—C4—H4A108.8C18—C19—C20121.6 (2)
C5—C4—H4B108.8C20—C19—H19119.2
N2—C5—C4115.55 (18)C15—C20—C23121.82 (19)
N2—C5—H5A108.4C19—C20—C15117.6 (2)
N2—C5—H5B108.4C19—C20—C23120.6 (2)
C4—C5—H5A108.4C16—C21—H21A109.5
C4—C5—H5B108.4C16—C21—H21B109.5
H5A—C5—H5B107.5C16—C21—H21C109.5
C7—C6—N1118.44 (17)H21A—C21—H21B109.5
C11—C6—N1119.68 (17)H21A—C21—H21C109.5
C11—C6—C7121.64 (18)H21B—C21—H21C109.5
C6—C7—C12123.53 (18)C18—C22—H22A109.5
C8—C7—C6117.94 (18)C18—C22—H22B109.5
C8—C7—C12118.52 (18)C18—C22—H22C109.5
C7—C8—H8119.0H22A—C22—H22B109.5
C9—C8—C7122.01 (19)H22A—C22—H22C109.5
C9—C8—H8119.0H22B—C22—H22C109.5
C8—C9—C10118.34 (19)C20—C23—H23A109.5
C8—C9—C13120.82 (19)C20—C23—H23B109.5
C10—C9—C13120.80 (19)C20—C23—H23C109.5
C9—C10—H10118.9H23A—C23—H23B109.5
C9—C10—C11122.14 (19)H23A—C23—H23C109.5
C11—C10—H10118.9H23B—C23—H23C109.5
C6—C11—C14123.29 (19)Cl1—C24—Cl2111.17 (15)
C10—C11—C6117.91 (19)Cl1—C24—H24A109.4
C10—C11—C14118.75 (19)Cl1—C24—H24B109.4
C7—C12—H12A109.5Cl2—C24—H24A109.4
C7—C12—H12B109.5Cl2—C24—H24B109.4
C7—C12—H12C109.5H24A—C24—H24B108.0
H12A—C12—H12B109.5
N1—C2—C3—C452.9 (3)C6—C7—C8—C90.3 (3)
N1—C6—C7—C8175.98 (18)C7—C6—C11—C102.2 (3)
N1—C6—C7—C122.7 (3)C7—C6—C11—C14175.1 (2)
N1—C6—C11—C10176.54 (18)C7—C8—C9—C100.3 (3)
N1—C6—C11—C140.7 (3)C7—C8—C9—C13177.99 (19)
N2—C15—C16—C17174.89 (19)C8—C9—C10—C110.4 (3)
N2—C15—C16—C215.0 (3)C9—C10—C11—C61.6 (3)
N2—C15—C20—C19174.33 (18)C9—C10—C11—C14175.8 (2)
N2—C15—C20—C236.8 (3)C11—C6—C7—C81.5 (3)
C1—N1—C2—C382.9 (2)C11—C6—C7—C12177.10 (19)
C1—N1—C6—C7118.8 (2)C12—C7—C8—C9178.42 (19)
C1—N1—C6—C1166.7 (3)C13—C9—C10—C11177.3 (2)
C1—N2—C5—C427.3 (3)C15—N2—C1—Se120.8 (2)
C1—N2—C15—C1684.3 (2)C15—N2—C1—N1160.43 (19)
C1—N2—C15—C20100.9 (2)C15—N2—C5—C4154.56 (18)
C2—N1—C1—Se1162.61 (14)C15—C16—C17—C181.5 (3)
C2—N1—C1—N218.7 (3)C16—C15—C20—C190.2 (3)
C2—N1—C6—C762.0 (2)C16—C15—C20—C23178.7 (2)
C2—N1—C6—C11112.6 (2)C16—C17—C18—C192.0 (4)
C2—C3—C4—C531.2 (3)C16—C17—C18—C22175.8 (2)
C3—C4—C5—N275.4 (3)C17—C18—C19—C201.4 (4)
C5—N2—C1—Se1161.26 (16)C18—C19—C20—C150.4 (3)
C5—N2—C1—N117.5 (3)C18—C19—C20—C23179.3 (2)
C5—N2—C15—C1693.9 (2)C20—C15—C16—C170.3 (3)
C5—N2—C15—C2080.8 (2)C20—C15—C16—C21179.6 (2)
C6—N1—C1—Se118.2 (3)C21—C16—C17—C18178.5 (2)
C6—N1—C1—N2160.53 (19)C22—C18—C19—C20176.4 (2)
C6—N1—C2—C396.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2B···I3i0.993.243.755 (2)114
C4—H4A···I3ii0.993.153.748 (2)120
C5—H5A···I1i0.993.093.930 (2)144
Symmetry codes: (i) x1, y, z; (ii) x1, y+1, z.
(SDiazMesSeDMK_I3_I2) top
Crystal data top
3.333(I1.5)·C26H35N2OSeF(000) = 4096
Mr = 1105.02Dx = 2.214 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 13.2501 (6) ÅCell parameters from 9214 reflections
b = 11.0708 (6) Åθ = 2.4–26.1°
c = 45.509 (3) ŵ = 5.81 mm1
β = 96.722 (2)°T = 100 K
V = 6629.7 (6) Å3Plate, red
Z = 80.17 × 0.15 × 0.05 mm
Data collection top
Bruker D8 Venture Photon 2
diffractometer
5737 reflections with I > 2σ(I)
Radiation source: Incoatec IµSRint = 0.041
φ and ω scansθmax = 26.2°, θmin = 2.4°
Absorption correction: multi-scan
SADABS v2016/2 (Bruker AXS Inc., 2017)
h = 1615
Tmin = 0.561, Tmax = 0.745k = 1313
46614 measured reflectionsl = 5656
6580 independent reflections
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.067Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142H-atom parameters constrained
S = 1.10 w = 1/[σ2(Fo2) + (0.018P)2 + 376.8008P]
where P = (Fo2 + 2Fc2)/3
6580 reflections(Δ/σ)max = 0.001
325 parametersΔρmax = 4.07 e Å3
0 restraintsΔρmin = 3.13 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
I10.5000000.5000000.5000000.0499 (3)
I20.59217 (7)0.28252 (10)0.48034 (2)0.0629 (3)
I30.43289 (6)0.24158 (7)0.42050 (2)0.0447 (2)
I40.30499 (7)0.20343 (7)0.36906 (2)0.0472 (2)
I50.14036 (7)0.19618 (11)0.30440 (2)0.0644 (3)
I60.0000000.19062 (9)0.2500000.0399 (3)
Se10.43060 (8)0.85323 (11)0.36915 (2)0.0365 (3)
O10.5273 (8)1.0240 (10)0.33671 (19)0.073 (4)
N10.2752 (7)0.6675 (9)0.36531 (18)0.044 (3)
N20.3725 (5)0.7013 (6)0.41039 (15)0.0162 (14)
C10.3465 (6)0.7280 (8)0.38187 (19)0.0193 (17)
C20.3169 (8)0.6205 (10)0.4295 (2)0.034 (2)
H2A0.3319840.6464550.4504150.041*
H2B0.3419890.5367480.4280520.041*
C30.2019 (10)0.6222 (13)0.4209 (3)0.053 (3)
H3A0.1796670.7052210.4152080.063*
H3B0.1670920.5974850.4380380.063*
C40.1723 (7)0.5353 (9)0.3947 (2)0.028 (2)
H4A0.1643830.4525610.4023710.033*
H4B0.1063320.5605570.3840220.033*
C50.2511 (10)0.5353 (10)0.3741 (3)0.041 (3)
H5A0.2265720.4886290.3560820.050*
H5B0.3136920.4962150.3836180.050*
C60.4604 (6)0.7580 (8)0.42725 (18)0.0182 (17)
C70.4461 (7)0.8626 (8)0.44333 (18)0.0201 (18)
C80.5304 (7)0.9104 (9)0.46074 (19)0.026 (2)
H80.5228670.9829260.4714100.031*
C90.6241 (7)0.8553 (9)0.46289 (19)0.025 (2)
C100.6357 (7)0.7511 (9)0.44608 (19)0.0232 (19)
H100.7009700.7150020.4467950.028*
C110.5552 (7)0.6996 (8)0.4285 (2)0.0220 (18)
C120.3427 (8)0.9228 (9)0.4419 (2)0.033 (2)
H12A0.3150410.9346700.4211960.049*
H12B0.3497521.0012680.4519320.049*
H12C0.2965890.8714260.4517350.049*
C130.7122 (8)0.9065 (10)0.4830 (2)0.036 (2)
H13A0.7104900.8752630.5031250.054*
H13B0.7072920.9948120.4832680.054*
H13C0.7762020.8827020.4758300.054*
C140.5692 (8)0.5867 (9)0.4110 (2)0.031 (2)
H14A0.5239560.5232470.4168640.047*
H14B0.6398830.5595040.4148860.047*
H14C0.5528010.6037540.3898570.047*
C150.2352 (7)0.7035 (10)0.3357 (2)0.029 (2)
C160.1632 (7)0.7955 (11)0.3313 (2)0.032 (2)
C170.1323 (7)0.8316 (10)0.3026 (2)0.030 (2)
H170.0850510.8961150.2992730.036*
C180.1684 (7)0.7761 (8)0.27840 (19)0.0214 (18)
C190.2352 (7)0.6804 (8)0.2838 (2)0.0231 (19)
H190.2579800.6391720.2675350.028*
C200.2703 (7)0.6424 (8)0.3125 (2)0.027 (2)
C210.1246 (9)0.8563 (15)0.3571 (3)0.059 (4)
H21A0.1807050.8983960.3687840.088*
H21B0.0959200.7957970.3694490.088*
H21C0.0718390.9147920.3499160.088*
C220.1392 (9)0.8227 (10)0.2475 (2)0.037 (2)
H22A0.0809590.7768170.2380380.055*
H22B0.1967650.8132700.2359290.055*
H22C0.1210550.9083380.2482650.055*
C230.3506 (10)0.5428 (10)0.3162 (3)0.044 (3)
H23A0.3196650.4678160.3222950.066*
H23B0.4056420.5668690.3313840.066*
H23C0.3781580.5298140.2973990.066*
C240.3949 (8)0.8837 (9)0.3274 (2)0.029 (2)
H24A0.4034210.8094570.3157660.035*
H24B0.3233030.9105060.3234200.035*
C250.4656 (7)0.9816 (9)0.3190 (2)0.027 (2)
C260.4475 (10)1.0260 (11)0.2879 (2)0.045 (3)
H26A0.3822201.0684890.2848510.068*
H26B0.4461760.9572860.2742730.068*
H26C0.5021861.0814010.2840990.068*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.0343 (5)0.0785 (8)0.0324 (5)0.0317 (6)0.0153 (4)0.0298 (5)
I20.0543 (5)0.0807 (7)0.0518 (5)0.0249 (5)0.0017 (4)0.0244 (5)
I30.0446 (4)0.0407 (4)0.0521 (5)0.0099 (3)0.0192 (4)0.0084 (3)
I40.0676 (5)0.0244 (4)0.0506 (5)0.0038 (4)0.0108 (4)0.0003 (3)
I50.0545 (5)0.0851 (7)0.0531 (5)0.0014 (5)0.0039 (4)0.0054 (5)
I60.0437 (6)0.0291 (5)0.0498 (6)0.0000.0178 (5)0.000
Se10.0389 (6)0.0451 (6)0.0225 (5)0.0279 (5)0.0089 (4)0.0138 (4)
O10.079 (7)0.092 (8)0.042 (5)0.069 (6)0.022 (5)0.028 (5)
N10.049 (6)0.058 (6)0.021 (4)0.043 (5)0.015 (4)0.017 (4)
N20.015 (3)0.017 (3)0.015 (3)0.008 (3)0.003 (3)0.001 (3)
C10.021 (4)0.020 (4)0.016 (4)0.001 (4)0.001 (3)0.001 (3)
C20.036 (6)0.043 (6)0.021 (5)0.019 (5)0.008 (4)0.012 (4)
C30.055 (8)0.061 (9)0.043 (7)0.022 (7)0.009 (6)0.002 (6)
C40.028 (5)0.030 (5)0.026 (5)0.012 (4)0.004 (4)0.002 (4)
C50.055 (7)0.028 (6)0.039 (6)0.008 (5)0.000 (5)0.002 (5)
C60.015 (4)0.021 (4)0.017 (4)0.007 (3)0.006 (3)0.002 (3)
C70.023 (4)0.022 (4)0.015 (4)0.002 (4)0.004 (3)0.002 (3)
C80.034 (5)0.031 (5)0.012 (4)0.017 (4)0.004 (4)0.002 (4)
C90.030 (5)0.031 (5)0.012 (4)0.012 (4)0.004 (3)0.005 (4)
C100.019 (4)0.029 (5)0.021 (4)0.003 (4)0.003 (3)0.006 (4)
C110.023 (4)0.022 (4)0.022 (4)0.004 (4)0.003 (4)0.007 (4)
C120.031 (5)0.024 (5)0.045 (6)0.003 (4)0.010 (5)0.008 (4)
C130.040 (6)0.035 (6)0.031 (5)0.016 (5)0.008 (5)0.002 (5)
C140.027 (5)0.026 (5)0.039 (6)0.002 (4)0.001 (4)0.002 (4)
C150.029 (5)0.041 (6)0.015 (4)0.019 (5)0.004 (4)0.008 (4)
C160.026 (5)0.050 (7)0.022 (5)0.019 (5)0.008 (4)0.010 (5)
C170.023 (5)0.032 (5)0.035 (5)0.004 (4)0.001 (4)0.004 (4)
C180.025 (5)0.021 (5)0.018 (4)0.007 (4)0.004 (3)0.001 (3)
C190.025 (5)0.022 (5)0.021 (4)0.005 (4)0.004 (4)0.002 (4)
C200.029 (5)0.019 (5)0.030 (5)0.010 (4)0.009 (4)0.005 (4)
C210.034 (6)0.102 (12)0.041 (7)0.010 (7)0.008 (5)0.031 (7)
C220.047 (6)0.041 (6)0.019 (5)0.003 (5)0.007 (4)0.010 (4)
C230.059 (8)0.024 (5)0.045 (7)0.002 (5)0.017 (6)0.002 (5)
C240.034 (5)0.034 (5)0.017 (4)0.017 (4)0.007 (4)0.007 (4)
C250.026 (5)0.029 (5)0.027 (5)0.012 (4)0.004 (4)0.002 (4)
C260.065 (8)0.041 (7)0.029 (6)0.022 (6)0.002 (5)0.009 (5)
Geometric parameters (Å, º) top
I1—I2i2.8887 (12)C12—H12B0.9800
I1—I22.8887 (12)C12—H12C0.9800
I3—I42.7570 (13)C13—H13A0.9800
I5—I62.9180 (10)C13—H13B0.9800
Se1—C11.911 (9)C13—H13C0.9800
Se1—C241.935 (9)C14—H14A0.9800
O1—C251.177 (12)C14—H14B0.9800
N1—C11.319 (12)C14—H14C0.9800
N1—C51.560 (14)C15—C161.393 (16)
N1—C151.446 (12)C15—C201.381 (15)
N2—C11.337 (11)C16—C171.383 (14)
N2—C21.501 (11)C16—C211.492 (15)
N2—C61.459 (10)C17—H170.9500
C2—H2A0.9900C17—C181.395 (13)
C2—H2B0.9900C18—C191.384 (13)
C2—C31.529 (16)C18—C221.507 (12)
C3—H3A0.9900C19—H190.9500
C3—H3B0.9900C19—C201.396 (13)
C3—C41.545 (16)C20—C231.528 (15)
C4—H4A0.9900C21—H21A0.9800
C4—H4B0.9900C21—H21B0.9800
C4—C51.485 (15)C21—H21C0.9800
C5—H5A0.9900C22—H22A0.9800
C5—H5B0.9900C22—H22B0.9800
C6—C71.395 (12)C22—H22C0.9800
C6—C111.408 (13)C23—H23A0.9800
C7—C81.396 (12)C23—H23B0.9800
C7—C121.518 (13)C23—H23C0.9800
C8—H80.9500C24—H24A0.9900
C8—C91.377 (14)C24—H24B0.9900
C9—C101.402 (14)C24—C251.510 (12)
C9—C131.508 (13)C25—C261.492 (14)
C10—H100.9500C26—H26A0.9800
C10—C111.379 (13)C26—H26B0.9800
C11—C141.507 (13)C26—H26C0.9800
C12—H12A0.9800
I2i—I1—I2180.00 (4)C9—C13—H13C109.5
I5ii—I6—I5177.58 (6)H13A—C13—H13B109.5
C1—Se1—C24109.9 (4)H13A—C13—H13C109.5
C1—N1—C5119.0 (8)H13B—C13—H13C109.5
C1—N1—C15123.6 (8)C11—C14—H14A109.5
C15—N1—C5115.6 (8)C11—C14—H14B109.5
C1—N2—C2127.4 (7)C11—C14—H14C109.5
C1—N2—C6121.0 (7)H14A—C14—H14B109.5
C6—N2—C2111.5 (7)H14A—C14—H14C109.5
N1—C1—Se1126.8 (7)H14B—C14—H14C109.5
N1—C1—N2121.9 (8)C16—C15—N1120.2 (10)
N2—C1—Se1111.2 (6)C20—C15—N1117.3 (10)
N2—C2—H2A109.1C20—C15—C16122.5 (9)
N2—C2—H2B109.1C15—C16—C21120.7 (10)
N2—C2—C3112.7 (8)C17—C16—C15117.8 (9)
H2A—C2—H2B107.8C17—C16—C21121.4 (11)
C3—C2—H2A109.1C16—C17—H17119.0
C3—C2—H2B109.1C16—C17—C18121.9 (10)
C2—C3—H3A109.6C18—C17—H17119.0
C2—C3—H3B109.6C17—C18—C22120.9 (9)
C2—C3—C4110.2 (11)C19—C18—C17117.9 (9)
H3A—C3—H3B108.1C19—C18—C22121.2 (9)
C4—C3—H3A109.6C18—C19—H19118.9
C4—C3—H3B109.6C18—C19—C20122.3 (9)
C3—C4—H4A109.5C20—C19—H19118.9
C3—C4—H4B109.5C15—C20—C19117.4 (9)
H4A—C4—H4B108.1C15—C20—C23124.1 (9)
C5—C4—C3110.8 (9)C19—C20—C23118.3 (9)
C5—C4—H4A109.5C16—C21—H21A109.5
C5—C4—H4B109.5C16—C21—H21B109.5
N1—C5—H5A109.7C16—C21—H21C109.5
N1—C5—H5B109.7H21A—C21—H21B109.5
C4—C5—N1110.0 (9)H21A—C21—H21C109.5
C4—C5—H5A109.7H21B—C21—H21C109.5
C4—C5—H5B109.7C18—C22—H22A109.5
H5A—C5—H5B108.2C18—C22—H22B109.5
C7—C6—N2119.0 (8)C18—C22—H22C109.5
C7—C6—C11122.3 (8)H22A—C22—H22B109.5
C11—C6—N2118.5 (8)H22A—C22—H22C109.5
C6—C7—C8117.6 (8)H22B—C22—H22C109.5
C6—C7—C12121.3 (8)C20—C23—H23A109.5
C8—C7—C12121.1 (8)C20—C23—H23B109.5
C7—C8—H8119.1C20—C23—H23C109.5
C9—C8—C7121.9 (9)H23A—C23—H23B109.5
C9—C8—H8119.1H23A—C23—H23C109.5
C8—C9—C10118.7 (8)H23B—C23—H23C109.5
C8—C9—C13120.3 (9)Se1—C24—H24A110.4
C10—C9—C13121.0 (9)Se1—C24—H24B110.4
C9—C10—H10119.0H24A—C24—H24B108.6
C11—C10—C9122.0 (9)C25—C24—Se1106.5 (6)
C11—C10—H10119.0C25—C24—H24A110.4
C6—C11—C14121.6 (8)C25—C24—H24B110.4
C10—C11—C6117.4 (9)O1—C25—C24121.2 (9)
C10—C11—C14121.0 (9)O1—C25—C26122.6 (9)
C7—C12—H12A109.5C26—C25—C24116.1 (8)
C7—C12—H12B109.5C25—C26—H26A109.5
C7—C12—H12C109.5C25—C26—H26B109.5
H12A—C12—H12B109.5C25—C26—H26C109.5
H12A—C12—H12C109.5H26A—C26—H26B109.5
H12B—C12—H12C109.5H26A—C26—H26C109.5
C9—C13—H13A109.5H26B—C26—H26C109.5
C9—C13—H13B109.5
Se1—C24—C25—O10.2 (14)C6—N2—C2—C3144.5 (9)
Se1—C24—C25—C26176.1 (8)C6—C7—C8—C91.9 (13)
N1—C15—C16—C17175.9 (9)C7—C6—C11—C101.3 (13)
N1—C15—C16—C211.3 (15)C7—C6—C11—C14180.0 (8)
N1—C15—C20—C19177.2 (8)C7—C8—C9—C102.7 (13)
N1—C15—C20—C232.0 (14)C7—C8—C9—C13177.1 (9)
N2—C2—C3—C482.5 (12)C8—C9—C10—C112.9 (13)
N2—C6—C7—C8176.0 (8)C9—C10—C11—C62.1 (13)
N2—C6—C7—C124.2 (13)C9—C10—C11—C14179.1 (8)
N2—C6—C11—C10176.1 (8)C11—C6—C7—C81.2 (13)
N2—C6—C11—C145.2 (12)C11—C6—C7—C12179.0 (9)
C1—N1—C5—C488.7 (13)C12—C7—C8—C9178.3 (9)
C1—N1—C15—C1679.1 (14)C13—C9—C10—C11177.0 (9)
C1—N1—C15—C20101.6 (13)C15—N1—C1—Se113.0 (17)
C1—N2—C2—C331.8 (15)C15—N1—C1—N2171.2 (10)
C1—N2—C6—C793.2 (10)C15—N1—C5—C4106.0 (11)
C1—N2—C6—C1191.8 (10)C15—C16—C17—C182.2 (14)
C2—N2—C1—Se1171.3 (8)C16—C15—C20—C193.5 (14)
C2—N2—C1—N112.4 (15)C16—C15—C20—C23178.8 (10)
C2—N2—C6—C783.4 (10)C16—C17—C18—C191.5 (14)
C2—N2—C6—C1191.6 (10)C16—C17—C18—C22175.7 (9)
C2—C3—C4—C535.6 (13)C17—C18—C19—C202.9 (14)
C3—C4—C5—N151.3 (12)C18—C19—C20—C150.5 (14)
C5—N1—C1—Se1151.0 (8)C18—C19—C20—C23175.0 (9)
C5—N1—C1—N224.8 (15)C20—C15—C16—C174.9 (14)
C5—N1—C15—C16116.4 (11)C20—C15—C16—C21177.9 (10)
C5—N1—C15—C2062.9 (12)C21—C16—C17—C18179.5 (10)
C6—N2—C1—Se14.7 (10)C22—C18—C19—C20174.2 (9)
C6—N2—C1—N1171.7 (9)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2A···I2i0.993.294.274 (10)173
C3—H3B···I2iii0.993.063.674 (14)122
C4—H4B···O1iv0.992.323.081 (13)133
C26—H26B···I6v0.983.264.186 (13)158
Symmetry codes: (i) x+1, y+1, z+1; (iii) x1/2, y+1/2, z; (iv) x1/2, y1/2, z; (v) x+1/2, y+1/2, z.
(SDiazMesSMIBK_I3) top
Crystal data top
I3·C29H41N2OSZ = 2
Mr = 846.40F(000) = 824
Triclinic, P1Dx = 1.726 Mg m3
a = 8.7838 (8) ÅMo Kα radiation, λ = 0.71073 Å
b = 14.2194 (15) ÅCell parameters from 9680 reflections
c = 15.1418 (15) Åθ = 2.6–29.2°
α = 63.522 (3)°µ = 2.97 mm1
β = 74.494 (4)°T = 100 K
γ = 80.494 (4)°Block, red
V = 1628.9 (3) Å30.11 × 0.09 × 0.08 mm
Data collection top
Bruker D8 Venture Photon 2
diffractometer
6624 reflections with I > 2σ(I)
Radiation source: Incoatec IµSRint = 0.052
φ and ω scansθmax = 29.2°, θmin = 2.4°
Absorption correction: multi-scan
SADABS v2016/2 (Bruker AXS Inc., 2017)
h = 1212
Tmin = 0.645, Tmax = 0.746k = 1919
60178 measured reflectionsl = 2020
8827 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033H-atom parameters constrained
wR(F2) = 0.069 w = 1/[σ2(Fo2) + 4.6197P]
where P = (Fo2 + 2Fc2)/3
S = 1.20(Δ/σ)max = 0.001
8827 reflectionsΔρmax = 2.75 e Å3
333 parametersΔρmin = 0.92 e Å3
0 restraints
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
I10.88921 (3)0.38632 (2)0.09024 (2)0.02408 (6)
I20.72699 (3)0.19081 (2)0.17581 (2)0.01934 (5)
I30.56631 (3)0.00606 (2)0.26107 (2)0.03233 (7)
S10.05667 (10)0.46475 (7)0.36526 (6)0.01818 (17)
O10.2113 (3)0.5914 (2)0.3362 (2)0.0295 (6)
N10.2562 (3)0.3008 (2)0.4062 (2)0.0158 (5)
N20.3781 (3)0.4598 (2)0.2983 (2)0.0151 (5)
C10.2498 (4)0.4050 (3)0.3507 (2)0.0160 (6)
C20.5358 (4)0.4062 (3)0.2800 (3)0.0187 (7)
H2A0.6062100.4568910.2208380.022*
H2B0.5239510.3480770.2636970.022*
C30.6117 (4)0.3626 (3)0.3700 (3)0.0200 (7)
H3A0.6410390.4214620.3790770.024*
H3B0.7097480.3206430.3570200.024*
C40.5003 (4)0.2931 (3)0.4671 (3)0.0202 (7)
H4A0.5639870.2417320.5148770.024*
H4B0.4339920.3376200.4993040.024*
C50.3934 (4)0.2340 (3)0.4472 (3)0.0178 (7)
H5A0.4567660.2060500.3984270.021*
H5B0.3530080.1732770.5110800.021*
C60.3726 (4)0.5737 (3)0.2502 (2)0.0151 (6)
C70.3515 (4)0.6310 (3)0.3078 (2)0.0153 (6)
C80.3463 (4)0.7401 (3)0.2572 (3)0.0195 (7)
H80.3321010.7803180.2950490.023*
C90.3611 (4)0.7927 (3)0.1525 (3)0.0192 (7)
C100.3879 (4)0.7326 (3)0.0981 (3)0.0202 (7)
H100.4017500.7673180.0266040.024*
C110.3952 (4)0.6237 (3)0.1443 (2)0.0170 (6)
C120.3351 (4)0.5792 (3)0.4206 (3)0.0224 (7)
H12A0.2586250.5242350.4511060.034*
H12B0.2980350.6318140.4478620.034*
H12C0.4380030.5476260.4362870.034*
C130.3458 (5)0.9107 (3)0.1011 (3)0.0294 (9)
H13A0.2420980.9354080.1296880.044*
H13B0.3562520.9334940.0284830.044*
H13C0.4292370.9401710.1115800.044*
C140.4249 (4)0.5623 (3)0.0809 (3)0.0238 (8)
H14A0.5384340.5444170.0646350.036*
H14B0.3881980.6051430.0181360.036*
H14C0.3672880.4975420.1187800.036*
C150.1242 (4)0.2398 (3)0.4238 (3)0.0171 (7)
C160.0226 (4)0.2008 (3)0.5195 (3)0.0184 (7)
C170.0977 (4)0.1388 (3)0.5347 (3)0.0184 (7)
H170.1688820.1119070.5987840.022*
C180.1165 (4)0.1151 (3)0.4582 (3)0.0200 (7)
C190.0101 (4)0.1540 (3)0.3647 (3)0.0202 (7)
H190.0210120.1374110.3125670.024*
C200.1119 (4)0.2167 (3)0.3459 (3)0.0179 (7)
C210.0412 (4)0.2253 (3)0.6031 (3)0.0242 (8)
H21A0.0467360.1974070.6615880.036*
H21B0.0408690.3017330.5793340.036*
H21C0.1414340.1928310.6227100.036*
C220.2460 (4)0.0465 (3)0.4764 (3)0.0231 (7)
H22A0.2035430.0263270.4945700.035*
H22B0.2861480.0716100.4147410.035*
H22C0.3322690.0497270.5316380.035*
C230.2274 (4)0.2545 (3)0.2448 (3)0.0226 (7)
H23A0.2149820.3312550.2095560.034*
H23B0.2064920.2225370.2039510.034*
H23C0.3355890.2342300.2551290.034*
C240.0261 (4)0.5487 (3)0.2388 (3)0.0241 (8)
H24A0.1077820.6014250.2012790.029*
H24B0.0313370.5063120.2009110.029*
C250.1369 (4)0.6023 (3)0.2527 (3)0.0206 (7)
C260.1986 (4)0.6679 (3)0.1584 (3)0.0253 (8)
H26A0.3067250.6962590.1776150.030*
H26B0.2062460.6219590.1263990.030*
C270.0964 (4)0.7601 (3)0.0801 (3)0.0228 (7)
H270.0094080.7306100.0559340.027*
C280.1738 (5)0.8212 (4)0.0097 (3)0.0357 (10)
H28A0.1885980.7735010.0372400.053*
H28B0.1058340.8772630.0620130.053*
H28C0.2767410.8521520.0121940.053*
C290.0716 (6)0.8313 (4)0.1254 (4)0.0385 (10)
H29A0.1744400.8596130.1510750.058*
H29B0.0072440.8894700.0732040.058*
H29C0.0172720.7908000.1809590.058*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.02009 (11)0.02643 (13)0.02587 (12)0.00218 (9)0.00205 (9)0.01254 (10)
I20.01807 (10)0.02349 (12)0.01696 (10)0.00023 (8)0.00447 (8)0.00909 (9)
I30.03382 (14)0.02925 (14)0.03432 (14)0.00730 (11)0.00552 (11)0.01298 (12)
S10.0152 (4)0.0163 (4)0.0195 (4)0.0007 (3)0.0043 (3)0.0048 (3)
O10.0204 (13)0.0303 (15)0.0268 (14)0.0029 (11)0.0008 (11)0.0064 (12)
N10.0140 (13)0.0140 (13)0.0205 (14)0.0013 (10)0.0065 (11)0.0067 (11)
N20.0142 (13)0.0135 (13)0.0182 (13)0.0003 (10)0.0037 (11)0.0073 (11)
C10.0185 (16)0.0162 (16)0.0158 (15)0.0021 (12)0.0058 (12)0.0087 (13)
C20.0161 (16)0.0189 (17)0.0195 (16)0.0011 (13)0.0021 (13)0.0083 (14)
C30.0161 (16)0.0196 (17)0.0238 (17)0.0014 (13)0.0052 (13)0.0081 (14)
C40.0198 (17)0.0187 (17)0.0249 (18)0.0005 (13)0.0100 (14)0.0090 (14)
C50.0158 (15)0.0145 (16)0.0228 (17)0.0026 (12)0.0095 (13)0.0059 (14)
C60.0143 (15)0.0134 (15)0.0170 (15)0.0017 (12)0.0037 (12)0.0054 (13)
C70.0130 (14)0.0175 (16)0.0174 (15)0.0005 (12)0.0032 (12)0.0096 (13)
C80.0169 (16)0.0200 (17)0.0252 (18)0.0003 (13)0.0048 (13)0.0130 (15)
C90.0153 (16)0.0163 (17)0.0224 (17)0.0033 (13)0.0056 (13)0.0033 (14)
C100.0194 (16)0.0217 (18)0.0151 (15)0.0058 (13)0.0035 (13)0.0024 (14)
C110.0144 (15)0.0200 (17)0.0180 (16)0.0010 (13)0.0060 (12)0.0085 (14)
C120.0252 (18)0.0248 (19)0.0189 (17)0.0015 (14)0.0050 (14)0.0106 (15)
C130.032 (2)0.0183 (19)0.031 (2)0.0063 (16)0.0062 (17)0.0036 (16)
C140.0276 (19)0.027 (2)0.0198 (17)0.0009 (15)0.0077 (15)0.0115 (15)
C150.0143 (15)0.0139 (16)0.0228 (17)0.0009 (12)0.0082 (13)0.0057 (13)
C160.0173 (16)0.0187 (17)0.0196 (16)0.0004 (13)0.0058 (13)0.0080 (14)
C170.0159 (15)0.0163 (16)0.0197 (16)0.0005 (12)0.0049 (13)0.0047 (14)
C180.0161 (16)0.0161 (17)0.0288 (18)0.0019 (13)0.0105 (14)0.0082 (14)
C190.0205 (17)0.0193 (17)0.0263 (18)0.0011 (13)0.0121 (14)0.0112 (15)
C200.0190 (16)0.0145 (16)0.0203 (16)0.0010 (13)0.0074 (13)0.0063 (13)
C210.0249 (18)0.031 (2)0.0218 (18)0.0037 (15)0.0044 (14)0.0151 (16)
C220.0187 (17)0.0194 (18)0.032 (2)0.0020 (14)0.0091 (15)0.0090 (16)
C230.0207 (17)0.0270 (19)0.0235 (18)0.0049 (14)0.0049 (14)0.0124 (15)
C240.0218 (18)0.030 (2)0.0185 (17)0.0027 (15)0.0073 (14)0.0087 (15)
C250.0160 (16)0.0157 (17)0.0249 (18)0.0036 (13)0.0043 (14)0.0032 (14)
C260.0222 (18)0.026 (2)0.0281 (19)0.0005 (15)0.0122 (15)0.0087 (16)
C270.0249 (18)0.0217 (18)0.0186 (17)0.0018 (14)0.0023 (14)0.0081 (15)
C280.039 (2)0.035 (2)0.0225 (19)0.0111 (19)0.0091 (17)0.0056 (18)
C290.046 (3)0.029 (2)0.045 (3)0.0039 (19)0.009 (2)0.020 (2)
Geometric parameters (Å, º) top
I1—I22.9235 (4)C14—H14A0.9800
I2—I32.9332 (5)C14—H14B0.9800
S1—C11.772 (3)C14—H14C0.9800
S1—C241.814 (4)C15—C161.399 (5)
O1—C251.212 (4)C15—C201.392 (5)
N1—C11.339 (4)C16—C171.395 (5)
N1—C51.496 (4)C16—C211.508 (5)
N1—C151.458 (4)C17—H170.9500
N2—C11.329 (4)C17—C181.397 (5)
N2—C21.486 (4)C18—C191.395 (5)
N2—C61.448 (4)C18—C221.510 (5)
C2—H2A0.9900C19—H190.9500
C2—H2B0.9900C19—C201.396 (5)
C2—C31.510 (5)C20—C231.509 (5)
C3—H3A0.9900C21—H21A0.9800
C3—H3B0.9900C21—H21B0.9800
C3—C41.533 (5)C21—H21C0.9800
C4—H4A0.9900C22—H22A0.9800
C4—H4B0.9900C22—H22B0.9800
C4—C51.522 (5)C22—H22C0.9800
C5—H5A0.9900C23—H23A0.9800
C5—H5B0.9900C23—H23B0.9800
C6—C71.399 (4)C23—H23C0.9800
C6—C111.406 (4)C24—H24A0.9900
C7—C81.389 (5)C24—H24B0.9900
C7—C121.503 (5)C24—C251.516 (5)
C8—H80.9500C25—C261.503 (5)
C8—C91.398 (5)C26—H26A0.9900
C9—C101.386 (5)C26—H26B0.9900
C9—C131.502 (5)C26—C271.537 (5)
C10—H100.9500C27—H271.0000
C10—C111.385 (5)C27—C281.520 (5)
C11—C141.514 (5)C27—C291.521 (5)
C12—H12A0.9800C28—H28A0.9800
C12—H12B0.9800C28—H28B0.9800
C12—H12C0.9800C28—H28C0.9800
C13—H13A0.9800C29—H29A0.9800
C13—H13B0.9800C29—H29B0.9800
C13—H13C0.9800C29—H29C0.9800
I1—I2—I3179.585 (12)H14B—C14—H14C109.5
C1—S1—C24106.62 (16)C16—C15—N1119.3 (3)
C1—N1—C5127.1 (3)C20—C15—N1117.9 (3)
C1—N1—C15119.5 (3)C20—C15—C16122.7 (3)
C15—N1—C5113.2 (3)C15—C16—C21121.5 (3)
C1—N2—C2121.0 (3)C17—C16—C15117.5 (3)
C1—N2—C6122.9 (3)C17—C16—C21121.0 (3)
C6—N2—C2115.9 (3)C16—C17—H17119.1
N1—C1—S1113.6 (2)C16—C17—C18121.8 (3)
N2—C1—S1123.0 (3)C18—C17—H17119.1
N2—C1—N1123.0 (3)C17—C18—C22121.1 (3)
N2—C2—H2A109.1C19—C18—C17118.6 (3)
N2—C2—H2B109.1C19—C18—C22120.3 (3)
N2—C2—C3112.6 (3)C18—C19—H19119.1
H2A—C2—H2B107.8C18—C19—C20121.7 (3)
C3—C2—H2A109.1C20—C19—H19119.1
C3—C2—H2B109.1C15—C20—C19117.7 (3)
C2—C3—H3A109.3C15—C20—C23122.2 (3)
C2—C3—H3B109.3C19—C20—C23120.0 (3)
C2—C3—C4111.6 (3)C16—C21—H21A109.5
H3A—C3—H3B108.0C16—C21—H21B109.5
C4—C3—H3A109.3C16—C21—H21C109.5
C4—C3—H3B109.3H21A—C21—H21B109.5
C3—C4—H4A109.1H21A—C21—H21C109.5
C3—C4—H4B109.1H21B—C21—H21C109.5
H4A—C4—H4B107.9C18—C22—H22A109.5
C5—C4—C3112.3 (3)C18—C22—H22B109.5
C5—C4—H4A109.1C18—C22—H22C109.5
C5—C4—H4B109.1H22A—C22—H22B109.5
N1—C5—C4113.2 (3)H22A—C22—H22C109.5
N1—C5—H5A108.9H22B—C22—H22C109.5
N1—C5—H5B108.9C20—C23—H23A109.5
C4—C5—H5A108.9C20—C23—H23B109.5
C4—C5—H5B108.9C20—C23—H23C109.5
H5A—C5—H5B107.7H23A—C23—H23B109.5
C7—C6—N2120.5 (3)H23A—C23—H23C109.5
C7—C6—C11121.6 (3)H23B—C23—H23C109.5
C11—C6—N2117.8 (3)S1—C24—H24A110.5
C6—C7—C12122.6 (3)S1—C24—H24B110.5
C8—C7—C6117.6 (3)H24A—C24—H24B108.7
C8—C7—C12119.8 (3)C25—C24—S1106.0 (2)
C7—C8—H8118.8C25—C24—H24A110.5
C7—C8—C9122.3 (3)C25—C24—H24B110.5
C9—C8—H8118.8O1—C25—C24120.5 (3)
C8—C9—C13120.8 (3)O1—C25—C26123.0 (3)
C10—C9—C8118.0 (3)C26—C25—C24116.5 (3)
C10—C9—C13121.2 (3)C25—C26—H26A108.7
C9—C10—H10118.9C25—C26—H26B108.7
C11—C10—C9122.3 (3)C25—C26—C27114.3 (3)
C11—C10—H10118.9H26A—C26—H26B107.6
C6—C11—C14122.1 (3)C27—C26—H26A108.7
C10—C11—C6118.1 (3)C27—C26—H26B108.7
C10—C11—C14119.8 (3)C26—C27—H27108.3
C7—C12—H12A109.5C28—C27—C26108.9 (3)
C7—C12—H12B109.5C28—C27—H27108.3
C7—C12—H12C109.5C28—C27—C29111.2 (3)
H12A—C12—H12B109.5C29—C27—C26111.8 (3)
H12A—C12—H12C109.5C29—C27—H27108.3
H12B—C12—H12C109.5C27—C28—H28A109.5
C9—C13—H13A109.5C27—C28—H28B109.5
C9—C13—H13B109.5C27—C28—H28C109.5
C9—C13—H13C109.5H28A—C28—H28B109.5
H13A—C13—H13B109.5H28A—C28—H28C109.5
H13A—C13—H13C109.5H28B—C28—H28C109.5
H13B—C13—H13C109.5C27—C29—H29A109.5
C11—C14—H14A109.5C27—C29—H29B109.5
C11—C14—H14B109.5C27—C29—H29C109.5
C11—C14—H14C109.5H29A—C29—H29B109.5
H14A—C14—H14B109.5H29A—C29—H29C109.5
H14A—C14—H14C109.5H29B—C29—H29C109.5
S1—C24—C25—O16.3 (4)C6—C7—C8—C90.1 (5)
S1—C24—C25—C26173.5 (3)C7—C6—C11—C103.3 (5)
O1—C25—C26—C27119.7 (4)C7—C6—C11—C14177.4 (3)
N1—C15—C16—C17177.1 (3)C7—C8—C9—C102.5 (5)
N1—C15—C16—C213.4 (5)C7—C8—C9—C13176.6 (3)
N1—C15—C20—C19177.0 (3)C8—C9—C10—C112.1 (5)
N1—C15—C20—C231.3 (5)C9—C10—C11—C60.7 (5)
N2—C2—C3—C452.3 (4)C9—C10—C11—C14180.0 (3)
N2—C6—C7—C8179.6 (3)C11—C6—C7—C82.9 (5)
N2—C6—C7—C120.6 (5)C11—C6—C7—C12176.9 (3)
N2—C6—C11—C10179.1 (3)C12—C7—C8—C9179.9 (3)
N2—C6—C11—C140.1 (5)C13—C9—C10—C11177.0 (3)
C1—S1—C24—C25177.9 (2)C15—N1—C1—S134.1 (4)
C1—N1—C5—C428.3 (5)C15—N1—C1—N2152.8 (3)
C1—N1—C15—C16106.6 (4)C15—N1—C5—C4157.3 (3)
C1—N1—C15—C2077.8 (4)C15—C16—C17—C180.6 (5)
C1—N2—C2—C379.9 (4)C16—C15—C20—C191.6 (5)
C1—N2—C6—C775.7 (4)C16—C15—C20—C23176.7 (3)
C1—N2—C6—C11106.7 (4)C16—C17—C18—C190.7 (5)
C2—N2—C1—S1174.2 (2)C16—C17—C18—C22179.1 (3)
C2—N2—C1—N113.4 (5)C17—C18—C19—C200.9 (5)
C2—N2—C6—C7108.4 (3)C18—C19—C20—C150.2 (5)
C2—N2—C6—C1169.2 (4)C18—C19—C20—C23178.2 (3)
C2—C3—C4—C533.1 (4)C20—C15—C16—C171.8 (5)
C3—C4—C5—N178.5 (4)C20—C15—C16—C21178.7 (3)
C5—N1—C1—S1151.9 (3)C21—C16—C17—C18179.9 (3)
C5—N1—C1—N221.2 (5)C22—C18—C19—C20179.3 (3)
C5—N1—C15—C1678.5 (4)C24—S1—C1—N1131.5 (3)
C5—N1—C15—C2097.0 (4)C24—S1—C1—N255.4 (3)
C6—N2—C1—S11.5 (4)C24—C25—C26—C2760.5 (4)
C6—N2—C1—N1171.0 (3)C25—C26—C27—C28178.6 (3)
C6—N2—C2—C3104.1 (3)C25—C26—C27—C2955.3 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2A···I10.993.073.693 (3)122
C2—H2B···I20.993.173.986 (3)141
(SDiazMesSeMIBK_I3) top
Crystal data top
I3·C29H41N2OSeZ = 2
Mr = 893.30F(000) = 860
Triclinic, P1Dx = 1.809 Mg m3
a = 8.8091 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 14.2584 (8) ÅCell parameters from 9322 reflections
c = 15.1228 (9) Åθ = 2.4–29.6°
α = 63.952 (2)°µ = 3.99 mm1
β = 74.061 (2)°T = 100 K
γ = 81.113 (2)°Block, red
V = 1639.67 (17) Å30.17 × 0.11 × 0.08 mm
Data collection top
Bruker D8 Venture Photon 2
diffractometer
7989 reflections with I > 2σ(I)
Radiation source: Incoatec IµSRint = 0.041
φ and ω scansθmax = 29.6°, θmin = 2.4°
Absorption correction: multi-scan
SADABS v2016/2 (Bruker AXS Inc., 2017)
h = 1212
Tmin = 0.640, Tmax = 0.746k = 1919
75078 measured reflectionsl = 2121
9229 independent reflections
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.024Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.052H-atom parameters constrained
S = 1.14 w = 1/[σ2(Fo2) + (0.0083P)2 + 2.5037P]
where P = (Fo2 + 2Fc2)/3
9229 reflections(Δ/σ)max = 0.001
333 parametersΔρmax = 1.18 e Å3
0 restraintsΔρmin = 1.66 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*/Ueq
I10.56024 (2)0.00543 (2)0.26292 (2)0.03391 (5)
I20.72482 (2)0.19059 (2)0.17544 (2)0.01934 (4)
I30.89122 (2)0.38487 (2)0.08800 (2)0.02363 (4)
Se10.04429 (2)0.46632 (2)0.36803 (2)0.01641 (5)
O10.2198 (2)0.59460 (14)0.33074 (14)0.0274 (4)
N10.2595 (2)0.29977 (14)0.40427 (14)0.0139 (3)
N20.3824 (2)0.45914 (14)0.29884 (14)0.0135 (3)
C10.2541 (2)0.40347 (16)0.35019 (16)0.0134 (4)
C20.5407 (2)0.40814 (17)0.27903 (17)0.0169 (4)
H2A0.6115340.4600620.2208700.020*
H2B0.5306120.3514430.2602540.020*
C30.6152 (3)0.36290 (18)0.36972 (18)0.0181 (4)
H3A0.6444870.4206060.3806850.022*
H3B0.7128840.3219430.3556650.022*
C40.5016 (3)0.29243 (18)0.46569 (18)0.0178 (4)
H4A0.5636580.2412700.5132730.021*
H4B0.4344250.3356730.4989700.021*
C50.3967 (3)0.23407 (17)0.44382 (18)0.0166 (4)
H5A0.4610210.2082120.3935460.020*
H5B0.3560230.1725880.5067830.020*
C60.3759 (2)0.57255 (16)0.25038 (16)0.0129 (4)
C70.3547 (2)0.62997 (17)0.30804 (16)0.0143 (4)
C80.3491 (3)0.73870 (17)0.25717 (18)0.0168 (4)
H80.3356720.7792500.2947840.020*
C90.3627 (3)0.78963 (17)0.15321 (18)0.0183 (4)
C100.3889 (3)0.72988 (18)0.09825 (17)0.0181 (4)
H100.4011980.7640830.0269510.022*
C110.3978 (3)0.62098 (17)0.14482 (16)0.0159 (4)
C120.3429 (3)0.57902 (18)0.42043 (17)0.0184 (4)
H12A0.4488860.5578140.4331040.028*
H12B0.2783940.5173850.4516220.028*
H12C0.2936790.6287030.4496760.028*
C130.3481 (3)0.90691 (19)0.1020 (2)0.0280 (5)
H13A0.2468850.9311390.1337950.042*
H13B0.3530460.9289930.0301350.042*
H13C0.4347920.9369810.1087880.042*
C140.4265 (3)0.55979 (19)0.08152 (18)0.0226 (5)
H14A0.3969470.6035600.0171420.034*
H14B0.3625860.4976580.1179160.034*
H14C0.5386050.5383990.0683640.034*
C150.1277 (2)0.23841 (16)0.42230 (17)0.0151 (4)
C160.1151 (3)0.21633 (17)0.34324 (17)0.0162 (4)
C170.0074 (3)0.15420 (18)0.36231 (18)0.0186 (4)
H170.0188670.1384940.3096450.022*
C180.1138 (3)0.11430 (17)0.45592 (18)0.0182 (4)
C190.0950 (3)0.13699 (17)0.53315 (18)0.0182 (4)
H190.1665410.1095870.5975020.022*
C200.0256 (3)0.19860 (17)0.51859 (17)0.0162 (4)
C210.2293 (3)0.2570 (2)0.24127 (18)0.0226 (5)
H21A0.2152370.3331000.2077420.034*
H21B0.2092520.2255860.1996500.034*
H21C0.3377440.2386550.2500640.034*
C220.2434 (3)0.04532 (18)0.4740 (2)0.0220 (5)
H22A0.2107890.0281300.5083580.033*
H22B0.2633910.0577480.4090590.033*
H22C0.3400880.0616440.5164260.033*
C230.0446 (3)0.2211 (2)0.60342 (18)0.0228 (5)
H23A0.0473130.1968100.6604920.034*
H23B0.0528150.2964900.5797080.034*
H23C0.1405510.1846590.6252130.034*
C240.0241 (3)0.5622 (2)0.23151 (19)0.0282 (6)
H24A0.1036820.6166170.1997860.034*
H24B0.0376240.5242160.1884180.034*
C250.1416 (3)0.61029 (18)0.24598 (19)0.0205 (5)
C260.1997 (3)0.6772 (2)0.1516 (2)0.0254 (5)
H26A0.3078910.7045260.1711660.030*
H26B0.2059610.6328440.1175310.030*
C270.0959 (3)0.76942 (19)0.07604 (18)0.0226 (5)
H270.0104480.7410900.0518360.027*
C280.1698 (4)0.8312 (2)0.0148 (2)0.0353 (7)
H28A0.1835140.7844910.0437190.053*
H28B0.1003310.8872860.0660100.053*
H28C0.2728470.8615280.0071790.053*
C290.0746 (4)0.8387 (2)0.1248 (3)0.0398 (7)
H29A0.1779810.8665570.1497140.060*
H29B0.0076560.8966250.0745560.060*
H29C0.0244200.7974180.1814490.060*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.03473 (10)0.03072 (10)0.03661 (10)0.00860 (7)0.00581 (8)0.01347 (8)
I20.01775 (7)0.02374 (8)0.01652 (7)0.00061 (5)0.00455 (5)0.00852 (6)
I30.01934 (7)0.02508 (8)0.02477 (8)0.00127 (6)0.00152 (6)0.01089 (7)
Se10.01227 (9)0.01410 (10)0.01832 (11)0.00093 (7)0.00392 (8)0.00298 (8)
O10.0189 (8)0.0255 (9)0.0243 (9)0.0011 (7)0.0009 (7)0.0013 (7)
N10.0127 (8)0.0116 (8)0.0175 (9)0.0005 (6)0.0067 (7)0.0047 (7)
N20.0129 (8)0.0132 (8)0.0141 (8)0.0005 (6)0.0045 (7)0.0050 (7)
C10.0137 (9)0.0131 (9)0.0150 (10)0.0015 (7)0.0065 (8)0.0062 (8)
C20.0132 (9)0.0156 (10)0.0204 (11)0.0015 (8)0.0020 (8)0.0080 (9)
C30.0150 (10)0.0159 (10)0.0229 (11)0.0006 (8)0.0072 (9)0.0065 (9)
C40.0176 (10)0.0163 (10)0.0215 (11)0.0001 (8)0.0102 (9)0.0066 (9)
C50.0156 (10)0.0119 (10)0.0219 (11)0.0015 (8)0.0093 (8)0.0043 (8)
C60.0112 (9)0.0113 (9)0.0151 (10)0.0010 (7)0.0033 (7)0.0043 (8)
C70.0110 (9)0.0151 (10)0.0166 (10)0.0005 (7)0.0036 (8)0.0062 (8)
C80.0149 (10)0.0146 (10)0.0221 (11)0.0002 (8)0.0051 (8)0.0085 (9)
C90.0162 (10)0.0138 (10)0.0217 (11)0.0016 (8)0.0052 (9)0.0037 (9)
C100.0168 (10)0.0184 (11)0.0149 (10)0.0023 (8)0.0048 (8)0.0022 (9)
C110.0147 (10)0.0187 (10)0.0135 (10)0.0002 (8)0.0044 (8)0.0056 (8)
C120.0223 (11)0.0191 (11)0.0152 (10)0.0011 (9)0.0056 (8)0.0075 (9)
C130.0322 (13)0.0155 (11)0.0295 (13)0.0036 (10)0.0079 (11)0.0021 (10)
C140.0303 (12)0.0224 (12)0.0168 (11)0.0013 (10)0.0083 (10)0.0088 (9)
C150.0146 (9)0.0109 (9)0.0212 (11)0.0003 (7)0.0081 (8)0.0060 (8)
C160.0150 (10)0.0148 (10)0.0184 (10)0.0009 (8)0.0064 (8)0.0056 (8)
C170.0190 (10)0.0180 (11)0.0235 (11)0.0011 (8)0.0105 (9)0.0101 (9)
C180.0163 (10)0.0124 (10)0.0259 (12)0.0012 (8)0.0110 (9)0.0049 (9)
C190.0154 (10)0.0145 (10)0.0209 (11)0.0009 (8)0.0042 (8)0.0039 (9)
C200.0171 (10)0.0129 (10)0.0194 (11)0.0021 (8)0.0079 (8)0.0061 (8)
C210.0225 (11)0.0290 (13)0.0187 (11)0.0047 (9)0.0042 (9)0.0113 (10)
C220.0176 (10)0.0176 (11)0.0311 (13)0.0030 (8)0.0098 (10)0.0072 (10)
C230.0234 (11)0.0260 (12)0.0214 (12)0.0052 (9)0.0046 (9)0.0111 (10)
C240.0201 (11)0.0400 (15)0.0175 (11)0.0078 (10)0.0069 (9)0.0073 (11)
C250.0151 (10)0.0165 (11)0.0241 (12)0.0020 (8)0.0060 (9)0.0020 (9)
C260.0184 (11)0.0269 (13)0.0269 (13)0.0019 (9)0.0116 (10)0.0049 (10)
C270.0223 (11)0.0213 (12)0.0187 (11)0.0035 (9)0.0032 (9)0.0059 (9)
C280.0377 (15)0.0317 (15)0.0253 (13)0.0128 (12)0.0098 (12)0.0049 (12)
C290.0489 (18)0.0298 (15)0.0427 (18)0.0024 (13)0.0096 (15)0.0172 (14)
Geometric parameters (Å, º) top
I1—I22.9351 (3)C14—H14A0.9800
I2—I32.9230 (3)C14—H14B0.9800
Se1—C11.928 (2)C14—H14C0.9800
Se1—C241.952 (2)C15—C161.398 (3)
O1—C251.216 (3)C15—C201.401 (3)
N1—C11.340 (3)C16—C171.390 (3)
N1—C51.500 (3)C16—C211.506 (3)
N1—C151.456 (3)C17—H170.9500
N2—C11.328 (3)C17—C181.391 (3)
N2—C21.487 (3)C18—C191.397 (3)
N2—C61.452 (3)C18—C221.512 (3)
C2—H2A0.9900C19—H190.9500
C2—H2B0.9900C19—C201.392 (3)
C2—C31.521 (3)C20—C231.508 (3)
C3—H3A0.9900C21—H21A0.9800
C3—H3B0.9900C21—H21B0.9800
C3—C41.533 (3)C21—H21C0.9800
C4—H4A0.9900C22—H22A0.9800
C4—H4B0.9900C22—H22B0.9800
C4—C51.518 (3)C22—H22C0.9800
C5—H5A0.9900C23—H23A0.9800
C5—H5B0.9900C23—H23B0.9800
C6—C71.399 (3)C23—H23C0.9800
C6—C111.402 (3)C24—H24A0.9900
C7—C81.395 (3)C24—H24B0.9900
C7—C121.506 (3)C24—C251.515 (3)
C8—H80.9500C25—C261.504 (3)
C8—C91.391 (3)C26—H26A0.9900
C9—C101.388 (3)C26—H26B0.9900
C9—C131.505 (3)C26—C271.533 (4)
C10—H100.9500C27—H271.0000
C10—C111.395 (3)C27—C281.529 (4)
C11—C141.508 (3)C27—C291.526 (4)
C12—H12A0.9800C28—H28A0.9800
C12—H12B0.9800C28—H28B0.9800
C12—H12C0.9800C28—H28C0.9800
C13—H13A0.9800C29—H29A0.9800
C13—H13B0.9800C29—H29B0.9800
C13—H13C0.9800C29—H29C0.9800
I3—I2—I1179.522 (8)H14B—C14—H14C109.5
C1—Se1—C24104.88 (10)C16—C15—N1117.64 (19)
C1—N1—C5126.80 (18)C16—C15—C20122.8 (2)
C1—N1—C15119.86 (17)C20—C15—N1119.43 (19)
C15—N1—C5113.14 (16)C15—C16—C21122.0 (2)
C1—N2—C2121.40 (18)C17—C16—C15117.3 (2)
C1—N2—C6122.66 (17)C17—C16—C21120.7 (2)
C6—N2—C2115.68 (17)C16—C17—H17118.9
N1—C1—Se1113.47 (15)C16—C17—C18122.2 (2)
N2—C1—Se1122.89 (15)C18—C17—H17118.9
N2—C1—N1123.18 (19)C17—C18—C19118.5 (2)
N2—C2—H2A109.0C17—C18—C22120.5 (2)
N2—C2—H2B109.0C19—C18—C22121.0 (2)
N2—C2—C3112.86 (18)C18—C19—H19119.0
H2A—C2—H2B107.8C20—C19—C18121.9 (2)
C3—C2—H2A109.0C20—C19—H19119.0
C3—C2—H2B109.0C15—C20—C23121.7 (2)
C2—C3—H3A109.4C19—C20—C15117.3 (2)
C2—C3—H3B109.4C19—C20—C23121.0 (2)
C2—C3—C4111.36 (18)C16—C21—H21A109.5
H3A—C3—H3B108.0C16—C21—H21B109.5
C4—C3—H3A109.4C16—C21—H21C109.5
C4—C3—H3B109.4H21A—C21—H21B109.5
C3—C4—H4A109.1H21A—C21—H21C109.5
C3—C4—H4B109.1H21B—C21—H21C109.5
H4A—C4—H4B107.8C18—C22—H22A109.5
C5—C4—C3112.51 (19)C18—C22—H22B109.5
C5—C4—H4A109.1C18—C22—H22C109.5
C5—C4—H4B109.1H22A—C22—H22B109.5
N1—C5—C4113.31 (17)H22A—C22—H22C109.5
N1—C5—H5A108.9H22B—C22—H22C109.5
N1—C5—H5B108.9C20—C23—H23A109.5
C4—C5—H5A108.9C20—C23—H23B109.5
C4—C5—H5B108.9C20—C23—H23C109.5
H5A—C5—H5B107.7H23A—C23—H23B109.5
C7—C6—N2120.19 (19)H23A—C23—H23C109.5
C7—C6—C11122.0 (2)H23B—C23—H23C109.5
C11—C6—N2117.75 (19)Se1—C24—H24A110.8
C6—C7—C12122.61 (19)Se1—C24—H24B110.8
C8—C7—C6117.5 (2)H24A—C24—H24B108.9
C8—C7—C12119.9 (2)C25—C24—Se1104.59 (16)
C7—C8—H8118.9C25—C24—H24A110.8
C9—C8—C7122.1 (2)C25—C24—H24B110.8
C9—C8—H8118.9O1—C25—C24119.9 (2)
C8—C9—C13120.5 (2)O1—C25—C26123.4 (2)
C10—C9—C8118.5 (2)C26—C25—C24116.6 (2)
C10—C9—C13121.0 (2)C25—C26—H26A108.7
C9—C10—H10119.1C25—C26—H26B108.7
C9—C10—C11121.8 (2)C25—C26—C27114.3 (2)
C11—C10—H10119.1H26A—C26—H26B107.6
C6—C11—C14122.5 (2)C27—C26—H26A108.7
C10—C11—C6117.9 (2)C27—C26—H26B108.7
C10—C11—C14119.6 (2)C26—C27—H27108.3
C7—C12—H12A109.5C28—C27—C26108.7 (2)
C7—C12—H12B109.5C28—C27—H27108.3
C7—C12—H12C109.5C29—C27—C26111.7 (2)
H12A—C12—H12B109.5C29—C27—H27108.3
H12A—C12—H12C109.5C29—C27—C28111.4 (2)
H12B—C12—H12C109.5C27—C28—H28A109.5
C9—C13—H13A109.5C27—C28—H28B109.5
C9—C13—H13B109.5C27—C28—H28C109.5
C9—C13—H13C109.5H28A—C28—H28B109.5
H13A—C13—H13B109.5H28A—C28—H28C109.5
H13A—C13—H13C109.5H28B—C28—H28C109.5
H13B—C13—H13C109.5C27—C29—H29A109.5
C11—C14—H14A109.5C27—C29—H29B109.5
C11—C14—H14B109.5C27—C29—H29C109.5
C11—C14—H14C109.5H29A—C29—H29B109.5
H14A—C14—H14B109.5H29A—C29—H29C109.5
H14A—C14—H14C109.5H29B—C29—H29C109.5
Se1—C24—C25—O18.9 (3)C6—C7—C8—C90.5 (3)
Se1—C24—C25—C26171.74 (18)C7—C6—C11—C103.6 (3)
O1—C25—C26—C27121.8 (3)C7—C6—C11—C14177.8 (2)
N1—C15—C16—C17177.50 (19)C7—C8—C9—C102.6 (3)
N1—C15—C16—C212.1 (3)C7—C8—C9—C13176.9 (2)
N1—C15—C20—C19177.53 (19)C8—C9—C10—C111.7 (3)
N1—C15—C20—C232.5 (3)C9—C10—C11—C61.3 (3)
N2—C2—C3—C451.5 (2)C9—C10—C11—C14180.0 (2)
N2—C6—C7—C8179.91 (18)C11—C6—C7—C82.7 (3)
N2—C6—C7—C122.0 (3)C11—C6—C7—C12175.4 (2)
N2—C6—C11—C10178.95 (18)C12—C7—C8—C9178.7 (2)
N2—C6—C11—C140.3 (3)C13—C9—C10—C11177.9 (2)
C1—N1—C5—C429.1 (3)C15—N1—C1—Se133.5 (2)
C1—N1—C15—C1677.8 (3)C15—N1—C1—N2154.0 (2)
C1—N1—C15—C20106.3 (2)C15—N1—C5—C4156.09 (19)
C1—N2—C2—C379.4 (2)C15—C16—C17—C180.4 (3)
C1—N2—C6—C777.7 (3)C16—C15—C20—C191.8 (3)
C1—N2—C6—C11104.7 (2)C16—C15—C20—C23178.2 (2)
C2—N2—C1—Se1174.64 (15)C16—C17—C18—C190.6 (3)
C2—N2—C1—N113.6 (3)C16—C17—C18—C22178.8 (2)
C2—N2—C6—C7108.1 (2)C17—C18—C19—C200.5 (3)
C2—N2—C6—C1169.4 (2)C18—C19—C20—C150.6 (3)
C2—C3—C4—C533.7 (3)C18—C19—C20—C23179.4 (2)
C3—C4—C5—N179.3 (2)C20—C15—C16—C171.7 (3)
C5—N1—C1—Se1152.00 (17)C20—C15—C16—C21177.9 (2)
C5—N1—C1—N220.5 (3)C21—C16—C17—C18179.2 (2)
C5—N1—C15—C1697.4 (2)C22—C18—C19—C20178.7 (2)
C5—N1—C15—C2078.6 (2)C24—C25—C26—C2757.6 (3)
C6—N2—C1—Se10.8 (3)C25—C26—C27—C28179.1 (2)
C6—N2—C1—N1172.55 (19)C25—C26—C27—C2955.8 (3)
C6—N2—C2—C3106.4 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2A···I30.993.103.690 (2)120
C2—H2B···I20.993.164.003 (2)144
C3—H3A···O1i0.992.633.560 (3)156
Symmetry code: (i) x+1, y, z.
(SDiazMesS_12F4DIB) top
Crystal data top
C6F4I2·C23H30N2SDx = 1.765 Mg m3
Mr = 768.41Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21Cell parameters from 9353 reflections
a = 7.6668 (5) Åθ = 2.9–28.4°
b = 16.8546 (11) ŵ = 2.30 mm1
c = 22.3786 (15) ÅT = 100 K
V = 2891.8 (3) Å3Needle, colourless
Z = 40.22 × 0.07 × 0.07 mm
F(000) = 1504
Data collection top
Bruker D8 Venture Photon 2
diffractometer
6786 reflections with I > 2σ(I)
Radiation source: Incoatec IµSRint = 0.044
φ and ω scansθmax = 28.4°, θmin = 2.9°
Absorption correction: multi-scan
SADABS v2016/2 (Bruker AXS Inc., 2017)
h = 1010
Tmin = 0.621, Tmax = 0.746k = 2222
50096 measured reflectionsl = 2929
7186 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.025H-atom parameters constrained
wR(F2) = 0.058 w = 1/[σ2(Fo2) + (0.0178P)2 + 2.9992P]
where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max = 0.002
7186 reflectionsΔρmax = 0.77 e Å3
349 parametersΔρmin = 0.70 e Å3
1 restraintAbsolute structure: Flack x determined using 3124 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
Primary atom site location: dualAbsolute structure parameter: 0.025 (7)
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
I10.76980 (3)0.62670 (2)0.46051 (2)0.02765 (7)
I20.97868 (5)0.51579 (2)0.33758 (2)0.04162 (10)
S10.60961 (14)0.55911 (7)0.58283 (5)0.0232 (2)
F11.1171 (5)0.6411 (2)0.24692 (15)0.0512 (9)
F21.1071 (5)0.8009 (2)0.24353 (15)0.0501 (9)
F30.9486 (4)0.88308 (16)0.33257 (17)0.0420 (8)
F40.8078 (4)0.80691 (16)0.42584 (13)0.0328 (6)
N10.3091 (5)0.5365 (2)0.63715 (19)0.0265 (8)
N20.3786 (5)0.4428 (2)0.5645 (2)0.0305 (9)
C10.4198 (6)0.5102 (2)0.5951 (2)0.0200 (9)
C20.1806 (8)0.4819 (4)0.6655 (3)0.0432 (14)
H2A0.2299760.4276540.6671540.052*
H2B0.1572120.4994720.7069110.052*
C30.0158 (8)0.4806 (4)0.6313 (3)0.0493 (16)
H3A0.0460600.5316890.6367810.059*
H3B0.0601450.4377400.6467150.059*
C40.0508 (7)0.4673 (4)0.5657 (3)0.0431 (14)
H4A0.0805310.5186100.5467030.052*
H4B0.0563220.4468800.5463920.052*
C50.2001 (8)0.4085 (4)0.5554 (3)0.0487 (15)
H5A0.1850250.3629810.5829010.058*
H5B0.1919280.3878800.5140450.058*
C60.3364 (6)0.6117 (3)0.6666 (2)0.0232 (9)
C70.4201 (6)0.6116 (3)0.7220 (2)0.0224 (9)
C80.4381 (6)0.6831 (3)0.7517 (2)0.0237 (9)
H80.4924270.6836360.7898880.028*
C90.3790 (5)0.7543 (3)0.72750 (19)0.0215 (8)
C100.2966 (6)0.7529 (3)0.6722 (2)0.0233 (9)
H100.2550330.8009200.6551680.028*
C110.2742 (6)0.6814 (3)0.6412 (2)0.0240 (9)
C120.4979 (7)0.5365 (3)0.7482 (2)0.0328 (11)
H12A0.5666560.5497500.7836830.049*
H12B0.5732960.5111510.7183870.049*
H12C0.4038530.4999320.7592850.049*
C130.4087 (7)0.8325 (3)0.7592 (2)0.0290 (10)
H13A0.3559620.8304390.7990390.043*
H13B0.3550660.8754610.7360790.043*
H13C0.5342270.8422290.7629110.043*
C140.1852 (7)0.6816 (3)0.5808 (2)0.0359 (11)
H14A0.2651060.6603540.5505670.054*
H14B0.1526440.7360090.5701300.054*
H14C0.0801790.6484950.5825090.054*
C150.5100 (6)0.4061 (3)0.5274 (2)0.0246 (9)
C160.5122 (6)0.4250 (3)0.4669 (2)0.0298 (10)
C170.6364 (8)0.3875 (3)0.4312 (2)0.0357 (12)
H170.6410790.4003040.3899030.043*
C180.7511 (7)0.3334 (3)0.4533 (3)0.0339 (12)
C190.7444 (7)0.3146 (3)0.5140 (3)0.0327 (11)
H190.8230370.2763260.5296010.039*
C200.6242 (7)0.3511 (3)0.5523 (2)0.0262 (10)
C210.3875 (9)0.4837 (3)0.4399 (3)0.0436 (14)
H21A0.2695980.4612860.4397900.065*
H21B0.4231360.4954680.3987510.065*
H21C0.3885560.5326970.4634610.065*
C220.8837 (10)0.2938 (4)0.4130 (3)0.0569 (18)
H22A0.8482120.3002230.3711730.085*
H22B0.8906190.2371850.4226390.085*
H22C0.9982280.3183990.4189760.085*
C230.6163 (8)0.3323 (3)0.6176 (2)0.0380 (12)
H23A0.7161400.2989290.6285110.057*
H23B0.5077790.3038690.6263960.057*
H23C0.6200070.3816380.6407100.057*
C240.8881 (6)0.6816 (3)0.3862 (2)0.0245 (9)
C250.9652 (6)0.6393 (3)0.3394 (3)0.0286 (9)
C261.0380 (7)0.6802 (4)0.2921 (2)0.0347 (12)
C271.0339 (7)0.7622 (4)0.2899 (2)0.0349 (12)
C280.9552 (6)0.8040 (3)0.3352 (3)0.0304 (10)
C290.8843 (6)0.7634 (3)0.3828 (2)0.0263 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.02956 (14)0.02609 (13)0.02730 (13)0.00367 (11)0.00535 (16)0.00388 (13)
I20.0456 (2)0.03001 (16)0.0492 (2)0.00803 (14)0.01249 (18)0.01082 (18)
S10.0195 (5)0.0228 (5)0.0272 (5)0.0043 (4)0.0023 (4)0.0038 (4)
F10.055 (2)0.066 (2)0.0320 (17)0.0002 (18)0.0085 (15)0.0162 (17)
F20.053 (2)0.070 (2)0.0273 (16)0.0194 (19)0.0003 (15)0.0126 (16)
F30.0516 (19)0.0291 (14)0.0452 (19)0.0074 (13)0.0098 (16)0.0117 (15)
F40.0375 (16)0.0265 (14)0.0343 (16)0.0003 (12)0.0019 (13)0.0042 (12)
N10.0236 (19)0.0231 (19)0.033 (2)0.0070 (15)0.0090 (16)0.0065 (16)
N20.0211 (19)0.029 (2)0.042 (2)0.0035 (16)0.0062 (17)0.0102 (18)
C10.018 (2)0.0169 (19)0.025 (2)0.0008 (15)0.0025 (16)0.0050 (16)
C20.040 (3)0.042 (3)0.048 (3)0.009 (3)0.009 (3)0.000 (3)
C30.033 (3)0.049 (4)0.065 (4)0.001 (3)0.006 (3)0.001 (3)
C40.028 (3)0.037 (3)0.065 (4)0.000 (2)0.008 (3)0.006 (3)
C50.036 (3)0.041 (3)0.070 (4)0.008 (3)0.002 (3)0.013 (3)
C60.023 (2)0.022 (2)0.025 (2)0.0039 (17)0.0050 (17)0.0035 (17)
C70.025 (2)0.021 (2)0.021 (2)0.0015 (17)0.0059 (17)0.0036 (16)
C80.025 (2)0.029 (2)0.018 (2)0.0015 (18)0.0009 (16)0.0001 (17)
C90.019 (2)0.024 (2)0.021 (2)0.0004 (16)0.0032 (16)0.0038 (17)
C100.022 (2)0.025 (2)0.023 (2)0.0053 (17)0.0049 (17)0.0019 (18)
C110.020 (2)0.031 (2)0.021 (2)0.0016 (18)0.0005 (17)0.0008 (18)
C120.039 (3)0.025 (2)0.035 (3)0.005 (2)0.003 (2)0.010 (2)
C130.030 (2)0.024 (2)0.034 (3)0.0003 (19)0.001 (2)0.0079 (19)
C140.039 (3)0.040 (3)0.029 (2)0.009 (2)0.008 (2)0.002 (2)
C150.027 (2)0.018 (2)0.029 (2)0.0045 (17)0.0021 (18)0.0069 (17)
C160.037 (2)0.021 (2)0.032 (3)0.0034 (17)0.007 (2)0.003 (2)
C170.060 (4)0.025 (2)0.022 (2)0.008 (2)0.003 (2)0.0034 (19)
C180.042 (3)0.025 (2)0.035 (3)0.0017 (19)0.014 (2)0.006 (2)
C190.035 (3)0.021 (2)0.042 (3)0.005 (2)0.000 (2)0.005 (2)
C200.034 (3)0.020 (2)0.025 (2)0.0043 (18)0.0059 (19)0.0005 (17)
C210.050 (3)0.033 (3)0.048 (3)0.000 (2)0.021 (3)0.001 (2)
C220.071 (5)0.045 (4)0.055 (4)0.011 (3)0.027 (4)0.006 (3)
C230.051 (3)0.033 (3)0.030 (3)0.005 (2)0.002 (2)0.004 (2)
C240.026 (2)0.025 (2)0.023 (2)0.0027 (18)0.0068 (18)0.0032 (18)
C250.027 (2)0.031 (2)0.028 (2)0.0016 (18)0.008 (2)0.001 (2)
C260.034 (3)0.049 (3)0.022 (2)0.000 (2)0.004 (2)0.007 (2)
C270.036 (3)0.046 (3)0.023 (2)0.011 (2)0.007 (2)0.008 (2)
C280.029 (2)0.030 (2)0.033 (2)0.0037 (18)0.011 (2)0.009 (2)
C290.024 (2)0.027 (2)0.027 (2)