research papers
Heterocyclic 1,3-diazepine-based thiones and
as versatile halogen-bond acceptorsaDepartment 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
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 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.
Keywords: halogen bonding; thione; selone; organoiodine; cocrystal; diiodine.
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). The electrophilic region is referred to as the σ hole and is located at the `cap' on the halogen end of the and is accompanied by a `belt' of relatively higher electrostatic potential orthogonal to the bond (Murray et al., 2009; Politzer et al., 2010; Politzer & Murray, 2017). A similar electron density distribution is observed for the chalcogen atoms and is particularly pronounced for thiones and (Vogel et al., 2019). 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).
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), 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 of interhalogens to diselones, resulting in I—Se—X hypervalent systems is notable (Juárez-Pérez et al., 2011). 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,b; Peloquin, McCollum et al., 2021; Peloquin, Alapati et al., 2021).
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 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.
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) and its corresponding diazepinium bromide derivative (SDiazMesH)Br (Kolychev et al., 2009) was prepared by a modification of a literature procedure (Iglesias et al., 2008). 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) 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,a; Dolomanov et al., 2009). 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) and its corresponding diazepinium bromide derivative (SDiazMesH)Br, SDiazMesS and SDiazMesSe were prepared by a modification of literature procedures (Iglesias et al., 2008; Rais et al., 2016).
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 (∼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 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 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.
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).
.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) 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) 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 P21/c, whereas SDiazMesSe crystallizes in the orthorhombic Pbca (Fig. 1). 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 (Table 1). 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). 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 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.
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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).
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 . 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). 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 . 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 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). 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).
The use of acetone as the reaction solvent allowed access to new organic products resulting from forming a new ). 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). 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 . 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). 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.
between the chalcogen atom and a methyl carbon of acetone (Fig. 33.4. Cocrystallization of SDiazMesS and SDiazMesSe with iodofluorobenzenes
The cocrystal (SDiazMesS)·(1,2-F4DIB) crystallizes in the orthorhombic Pna21 with one molecule each of SDiazMesS and 1,2-F4DIB within the (Fig. 4). 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). 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.
With 1,3-F4DIB as the halogen bond donor, four cocrystalline structures were obtained (Fig. 5). The first two, (SDiazMesS)·(1,3-F4DIB) and (SDiazMesSe)·(1,3-F4DIB), are isomorphic. Both cocrsytals are obtained in the orthorhombic 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 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 π⋯π 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.
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 , and 2(SDiazMesS)·(1,4-F4DIB)m which crystallized in the monoclinic P21/c. The triclinic isomorph, 2(SDiazMesSe)·(1,4-F4DIB)t, was obtained with SDiazMesSe (Fig. 6). 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; Chernysheva & Haukka, 2021). 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].
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). In this pair, the structures are not isomorphic, with (SDiazMesS)·(1,3,5-F3I3B) crystallizing in the monoclinic P21/c and (SDiazMesSe)·(1,3,5-F3I3B) in 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.
With the halogen bond donor iodopentafluorobenzene (IF5B), different reaction conditions were required for SDiazMesS and SDiazMesSe, resulting in dramatically different cocrystalline structures (Fig. 8). By reacting five equivalents of IF5B with SDiazMesS in ethanol, (SDiazMesS)·(IF5B) was obtained in the orthorhombic 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). These halogen bonded pairs stack along the a axis through π⋯π 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 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). 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.
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 , with one thione or selone molecule and one half of a per A single halogen bond is observed to the chalcogen atom, contributing to discrete 2:1 units within the structure (Fig. 9). The remaining two iodine atoms of each 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.
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, 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
https://doi.org/10.1107/S2052520622008150/rm5061sup1.cif
contains datablocks SDiazMesS, SDiazMesSe, SDiazMesS_MeCN, SDiazMesSe_MeCN, SDiazMesSI2, SDiazMesSeI2, SDiazMesSI2_I2, SDiazMesSeI_I3, SDiazMesSeI_I3_DCM, SDiazMesSeDMK_I3_I2, SDiazMesSMIBK_I3, SDiazMesSeMIBK_I3, SDiazMesS_12F4DIB, SDiazMesS_13F4DIB, SDiazMesSe_13F4DIB, 2SDiazMesS_13F4DIB, 2SDiazMesSe_13F4DIB, 2SDiazMesS_14F4DIB_t, 2SDiazMesSe_14F4DIB_t, 2SDiazMesS_14F4DIB_m, SDiazMesS_135F3I3B, SDiazMesSe_135F3I3B, SDiazMesS_IF5B, 2SDiazMesSe_5F5IB, 2SDiazMesS_TIE, 2SDiazMesSe_TIE. DOI:Structure factors: contains datablock SDiazMesS. DOI: https://doi.org/10.1107/S2052520622008150/rm5061SDiazMesSsup2.hkl
Structure factors: contains datablock SDiazMesSe. DOI: https://doi.org/10.1107/S2052520622008150/rm5061SDiazMesSesup3.hkl
Structure factors: contains datablock SDiazMesS_MeCN. DOI: https://doi.org/10.1107/S2052520622008150/rm5061SDiazMesS_MeCNsup4.hkl
Structure factors: contains datablock SDiazMesSe_MeCN. DOI: https://doi.org/10.1107/S2052520622008150/rm5061SDiazMesSe_MeCNsup5.hkl
Structure factors: contains datablock SDiazMesSI2. DOI: https://doi.org/10.1107/S2052520622008150/rm5061SDiazMesSI2sup6.hkl
Structure factors: contains datablock SDiazMesSeI2. DOI: https://doi.org/10.1107/S2052520622008150/rm5061SDiazMesSeI2sup7.hkl
Structure factors: contains datablock SDiazMesSI2_I2. DOI: https://doi.org/10.1107/S2052520622008150/rm5061SDiazMesSI2_I2sup8.hkl
Structure factors: contains datablock SDiazMesSeI_I3. DOI: https://doi.org/10.1107/S2052520622008150/rm5061SDiazMesSeI_I3sup9.hkl
Structure factors: contains datablock SDiazMesSeI_I3_DCM. DOI: https://doi.org/10.1107/S2052520622008150/rm5061SDiazMesSeI_I3_DCMsup10.hkl
Structure factors: contains datablock SDiazMesSeDMK_I3_I2. DOI: https://doi.org/10.1107/S2052520622008150/rm5061SDiazMesSeDMK_I3_I2sup11.hkl
Structure factors: contains datablock SDiazMesSMIBK_I3. DOI: https://doi.org/10.1107/S2052520622008150/rm5061SDiazMesSMIBK_I3sup12.hkl
Structure factors: contains datablock SDiazMesSeMIBK_I3. DOI: https://doi.org/10.1107/S2052520622008150/rm5061SDiazMesSeMIBK_I3sup13.hkl
Structure factors: contains datablock SDiazMesS_12F4DIB. DOI: https://doi.org/10.1107/S2052520622008150/rm5061SDiazMesS_12F4DIBsup14.hkl
Structure factors: contains datablock SDiazMesS_13F4DIB. DOI: https://doi.org/10.1107/S2052520622008150/rm5061SDiazMesS_13F4DIBsup15.hkl
Structure factors: contains datablock SDiazMesSe_13F4DIB. DOI: https://doi.org/10.1107/S2052520622008150/rm5061SDiazMesSe_13F4DIBsup16.hkl
Structure factors: contains datablock 2SDiazMesS_13F4DIB. DOI: https://doi.org/10.1107/S2052520622008150/rm50612SDiazMesS_13F4DIBsup17.hkl
Structure factors: contains datablock 2SDiazMesSe_13F4DIB. DOI: https://doi.org/10.1107/S2052520622008150/rm50612SDiazMesSe_13F4DIBsup18.hkl
Structure factors: contains datablock 2SDiazMesS_14F4DIB_t. DOI: https://doi.org/10.1107/S2052520622008150/rm50612SDiazMesS_14F4DIB_tsup19.hkl
Structure factors: contains datablock 2SDiazMesSe_14F4DIB_t. DOI: https://doi.org/10.1107/S2052520622008150/rm50612SDiazMesSe_14F4DIB_tsup20.hkl
Structure factors: contains datablock 2SDiazMesS_14F4DIB_m. DOI: https://doi.org/10.1107/S2052520622008150/rm50612SDiazMesS_14F4DIB_msup21.hkl
Structure factors: contains datablock SDiazMesS_135F3I3B. DOI: https://doi.org/10.1107/S2052520622008150/rm5061SDiazMesS_135F3I3Bsup22.hkl
Structure factors: contains datablock SDiazMesSe_135F3I3B. DOI: https://doi.org/10.1107/S2052520622008150/rm5061SDiazMesSe_135F3I3Bsup23.hkl
Structure factors: contains datablock SDiazMesS_IF5B. DOI: https://doi.org/10.1107/S2052520622008150/rm5061SDiazMesS_IF5Bsup24.hkl
Structure factors: contains datablock 2SDiazMesSe_5F5IB. DOI: https://doi.org/10.1107/S2052520622008150/rm50612SDiazMesSe_5F5IBsup25.hkl
Structure factors: contains datablock 2SDiazMesS_TIE. DOI: https://doi.org/10.1107/S2052520622008150/rm50612SDiazMesS_TIEsup26.hkl
Structure factors: contains datablock 2SDiazMesSe_TIE. DOI: https://doi.org/10.1107/S2052520622008150/rm50612SDiazMesSe_TIEsup27.hkl
Tables S1-S24. DOI: https://doi.org/10.1107/S2052520622008150/rm5061sup28.pdf
For all structures, data collection: APEX3 v2017.3-0 (Bruker AXS Inc., 2017); cell
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).C23H30N2S | F(000) = 792 |
Mr = 366.55 | Dx = 1.186 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 16.4064 (14) Å | Cell parameters from 9938 reflections |
b = 8.7386 (9) Å | θ = 2.6–27.9° |
c = 14.8229 (14) Å | µ = 0.17 mm−1 |
β = 104.983 (3)° | T = 100 K |
V = 2052.9 (3) Å3 | Block, colourless |
Z = 4 | 0.30 × 0.19 × 0.17 mm |
Bruker D8 Venture Photon 2 diffractometer | 3717 reflections with I > 2σ(I) |
Radiation source: Incoatec IµS | Rint = 0.044 |
φ and ω scans | θmax = 26.5°, θmin = 2.6° |
Absorption correction: multi-scan SADABS v2016/2 (Bruker AXS Inc., 2017) | h = −20→19 |
Tmin = 0.706, Tmax = 0.746 | k = −10→10 |
33473 measured reflections | l = −18→18 |
4240 independent reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.097 | H-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 parameters | Δρmax = 0.37 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.69533 (2) | 0.74837 (4) | 0.29532 (2) | 0.01726 (10) | |
N1 | 0.80101 (7) | 0.72854 (13) | 0.46402 (8) | 0.0151 (2) | |
C1 | 0.71991 (8) | 0.75052 (14) | 0.41320 (9) | 0.0139 (3) | |
C2 | 0.82151 (9) | 0.67659 (17) | 0.56223 (9) | 0.0190 (3) | |
H2A | 0.875834 | 0.620679 | 0.576717 | 0.023* | |
H2B | 0.777332 | 0.604724 | 0.570419 | 0.023* | |
N2 | 0.65924 (7) | 0.77220 (13) | 0.45957 (8) | 0.0149 (2) | |
C3 | 0.82787 (9) | 0.80908 (19) | 0.63033 (10) | 0.0226 (3) | |
H3A | 0.879540 | 0.869083 | 0.632559 | 0.027* | |
H3B | 0.831765 | 0.768877 | 0.693744 | 0.027* | |
C4 | 0.75048 (9) | 0.91216 (17) | 0.59967 (10) | 0.0210 (3) | |
H4A | 0.743420 | 0.971097 | 0.654188 | 0.025* | |
H4B | 0.759687 | 0.986048 | 0.552646 | 0.025* | |
C5 | 0.67010 (9) | 0.82163 (17) | 0.55817 (9) | 0.0184 (3) | |
H5A | 0.669915 | 0.729642 | 0.597099 | 0.022* | |
H5B | 0.621009 | 0.885205 | 0.561472 | 0.022* | |
C7 | 0.89749 (8) | 0.57991 (16) | 0.39698 (9) | 0.0170 (3) | |
C6 | 0.86912 (8) | 0.72241 (16) | 0.41884 (9) | 0.0157 (3) | |
C9 | 1.00943 (9) | 0.70720 (19) | 0.34508 (10) | 0.0213 (3) | |
C8 | 0.96802 (9) | 0.57501 (17) | 0.36037 (9) | 0.0196 (3) | |
H8 | 0.988079 | 0.478646 | 0.345599 | 0.024* | |
C10 | 0.97800 (9) | 0.84722 (17) | 0.36537 (10) | 0.0201 (3) | |
H10 | 1.004896 | 0.938571 | 0.353551 | 0.024* | |
C11 | 0.90822 (9) | 0.85794 (16) | 0.40253 (9) | 0.0175 (3) | |
C12 | 0.85341 (9) | 0.43400 (17) | 0.41083 (11) | 0.0228 (3) | |
H12A | 0.876495 | 0.396782 | 0.474710 | 0.034* | |
H12B | 0.862168 | 0.356645 | 0.366391 | 0.034* | |
H12C | 0.792865 | 0.453602 | 0.400395 | 0.034* | |
C13 | 1.08734 (10) | 0.6999 (2) | 0.30884 (13) | 0.0324 (4) | |
H13A | 1.137314 | 0.721830 | 0.359870 | 0.049* | |
H13B | 1.082865 | 0.775777 | 0.259110 | 0.049* | |
H13C | 1.092381 | 0.597390 | 0.284035 | 0.049* | |
C14 | 0.87597 (10) | 1.01221 (17) | 0.42238 (10) | 0.0233 (3) | |
H14A | 0.914717 | 1.091985 | 0.412426 | 0.035* | |
H14B | 0.872274 | 1.015614 | 0.487285 | 0.035* | |
H14C | 0.819916 | 1.029486 | 0.380350 | 0.035* | |
C15 | 0.57190 (8) | 0.75149 (16) | 0.40930 (9) | 0.0151 (3) | |
C16 | 0.52152 (9) | 0.87994 (16) | 0.37804 (9) | 0.0166 (3) | |
C17 | 0.43675 (9) | 0.85616 (17) | 0.33349 (10) | 0.0199 (3) | |
H17 | 0.401693 | 0.941873 | 0.311240 | 0.024* | |
C18 | 0.40206 (9) | 0.70968 (18) | 0.32076 (10) | 0.0223 (3) | |
C19 | 0.45411 (9) | 0.58466 (17) | 0.35178 (10) | 0.0210 (3) | |
H19 | 0.430990 | 0.484470 | 0.342404 | 0.025* | |
C20 | 0.53954 (9) | 0.60283 (16) | 0.39638 (9) | 0.0176 (3) | |
C21 | 0.55692 (9) | 1.03973 (16) | 0.39057 (10) | 0.0217 (3) | |
H21A | 0.520413 | 1.108131 | 0.345174 | 0.033* | |
H21B | 0.613724 | 1.039769 | 0.380716 | 0.033* | |
H21C | 0.559652 | 1.075316 | 0.453981 | 0.033* | |
C22 | 0.30947 (10) | 0.6871 (2) | 0.27393 (14) | 0.0358 (4) | |
H22A | 0.298031 | 0.577958 | 0.261797 | 0.054* | |
H22B | 0.294632 | 0.743469 | 0.214758 | 0.054* | |
H22C | 0.275699 | 0.725370 | 0.314851 | 0.054* | |
C23 | 0.59506 (10) | 0.46490 (17) | 0.42671 (11) | 0.0235 (3) | |
H23A | 0.559768 | 0.373804 | 0.424544 | 0.035* | |
H23B | 0.629714 | 0.480296 | 0.490622 | 0.035* | |
H23C | 0.631789 | 0.450947 | 0.384670 | 0.035* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.01580 (18) | 0.0250 (2) | 0.01103 (17) | 0.00180 (13) | 0.00354 (13) | −0.00034 (13) |
N1 | 0.0139 (5) | 0.0195 (6) | 0.0125 (5) | 0.0013 (4) | 0.0040 (4) | 0.0016 (4) |
C1 | 0.0159 (6) | 0.0117 (6) | 0.0144 (6) | −0.0006 (5) | 0.0042 (5) | −0.0001 (5) |
C2 | 0.0166 (6) | 0.0254 (7) | 0.0145 (6) | 0.0021 (6) | 0.0031 (5) | 0.0054 (6) |
N2 | 0.0134 (5) | 0.0200 (6) | 0.0113 (5) | −0.0009 (4) | 0.0029 (4) | −0.0024 (4) |
C3 | 0.0186 (7) | 0.0353 (8) | 0.0132 (6) | −0.0041 (6) | 0.0028 (5) | −0.0007 (6) |
C4 | 0.0226 (7) | 0.0249 (7) | 0.0159 (7) | −0.0040 (6) | 0.0056 (5) | −0.0050 (6) |
C5 | 0.0189 (7) | 0.0257 (7) | 0.0117 (6) | −0.0007 (6) | 0.0058 (5) | −0.0028 (5) |
C7 | 0.0147 (6) | 0.0204 (7) | 0.0147 (6) | 0.0007 (5) | 0.0015 (5) | 0.0010 (5) |
C6 | 0.0127 (6) | 0.0214 (7) | 0.0125 (6) | 0.0003 (5) | 0.0025 (5) | 0.0008 (5) |
C9 | 0.0140 (6) | 0.0335 (8) | 0.0162 (7) | 0.0012 (6) | 0.0032 (5) | 0.0034 (6) |
C8 | 0.0165 (7) | 0.0245 (7) | 0.0174 (7) | 0.0047 (6) | 0.0033 (5) | 0.0002 (6) |
C10 | 0.0168 (7) | 0.0252 (7) | 0.0174 (7) | −0.0043 (6) | 0.0027 (5) | 0.0035 (6) |
C11 | 0.0165 (6) | 0.0207 (7) | 0.0137 (6) | −0.0007 (5) | 0.0010 (5) | 0.0006 (5) |
C12 | 0.0238 (7) | 0.0192 (7) | 0.0267 (8) | −0.0003 (6) | 0.0088 (6) | −0.0008 (6) |
C13 | 0.0237 (8) | 0.0416 (10) | 0.0369 (9) | 0.0030 (7) | 0.0168 (7) | 0.0054 (8) |
C14 | 0.0270 (8) | 0.0193 (7) | 0.0236 (7) | −0.0023 (6) | 0.0066 (6) | −0.0003 (6) |
C15 | 0.0138 (6) | 0.0204 (7) | 0.0120 (6) | −0.0006 (5) | 0.0049 (5) | −0.0011 (5) |
C16 | 0.0182 (7) | 0.0192 (7) | 0.0141 (6) | 0.0007 (5) | 0.0071 (5) | −0.0013 (5) |
C17 | 0.0182 (7) | 0.0241 (7) | 0.0172 (7) | 0.0058 (6) | 0.0044 (5) | −0.0034 (6) |
C18 | 0.0164 (7) | 0.0307 (8) | 0.0202 (7) | −0.0009 (6) | 0.0056 (6) | −0.0075 (6) |
C19 | 0.0192 (7) | 0.0221 (7) | 0.0233 (7) | −0.0053 (6) | 0.0085 (6) | −0.0059 (6) |
C20 | 0.0183 (7) | 0.0195 (7) | 0.0162 (6) | −0.0004 (5) | 0.0068 (5) | −0.0012 (5) |
C21 | 0.0237 (7) | 0.0183 (7) | 0.0237 (7) | 0.0001 (6) | 0.0069 (6) | −0.0007 (6) |
C22 | 0.0169 (8) | 0.0397 (10) | 0.0479 (11) | 0.0001 (7) | 0.0030 (7) | −0.0153 (8) |
C23 | 0.0259 (7) | 0.0180 (7) | 0.0264 (8) | 0.0000 (6) | 0.0066 (6) | 0.0009 (6) |
S1—C1 | 1.6887 (14) | C12—H12A | 0.9800 |
N1—C1 | 1.3625 (17) | C12—H12B | 0.9800 |
N1—C2 | 1.4783 (17) | C12—H12C | 0.9800 |
N1—C6 | 1.4447 (17) | C13—H13A | 0.9800 |
C1—N2 | 1.3611 (17) | C13—H13B | 0.9800 |
C2—H2A | 0.9900 | C13—H13C | 0.9800 |
C2—H2B | 0.9900 | C14—H14A | 0.9800 |
C2—C3 | 1.522 (2) | C14—H14B | 0.9800 |
N2—C5 | 1.4898 (16) | C14—H14C | 0.9800 |
N2—C15 | 1.4454 (17) | C15—C16 | 1.3999 (19) |
C3—H3A | 0.9900 | C15—C20 | 1.3977 (19) |
C3—H3B | 0.9900 | C16—C17 | 1.392 (2) |
C3—C4 | 1.527 (2) | C16—C21 | 1.505 (2) |
C4—H4A | 0.9900 | C17—H17 | 0.9500 |
C4—H4B | 0.9900 | C17—C18 | 1.394 (2) |
C4—C5 | 1.5245 (19) | C18—C19 | 1.390 (2) |
C5—H5A | 0.9900 | C18—C22 | 1.511 (2) |
C5—H5B | 0.9900 | C19—H19 | 0.9500 |
C7—C6 | 1.3965 (19) | C19—C20 | 1.396 (2) |
C7—C8 | 1.4001 (19) | C20—C23 | 1.508 (2) |
C7—C12 | 1.506 (2) | C21—H21A | 0.9800 |
C6—C11 | 1.3974 (19) | C21—H21B | 0.9800 |
C9—C8 | 1.388 (2) | C21—H21C | 0.9800 |
C9—C10 | 1.391 (2) | C22—H22A | 0.9800 |
C9—C13 | 1.510 (2) | C22—H22B | 0.9800 |
C8—H8 | 0.9500 | C22—H22C | 0.9800 |
C10—H10 | 0.9500 | C23—H23A | 0.9800 |
C10—C11 | 1.3961 (19) | C23—H23B | 0.9800 |
C11—C14 | 1.505 (2) | C23—H23C | 0.9800 |
C1—N1—C2 | 121.92 (11) | C7—C12—H12C | 109.5 |
C1—N1—C6 | 120.72 (11) | H12A—C12—H12B | 109.5 |
C6—N1—C2 | 116.02 (11) | H12A—C12—H12C | 109.5 |
N1—C1—S1 | 120.55 (10) | H12B—C12—H12C | 109.5 |
N2—C1—S1 | 120.92 (10) | C9—C13—H13A | 109.5 |
N2—C1—N1 | 118.52 (12) | C9—C13—H13B | 109.5 |
N1—C2—H2A | 109.2 | C9—C13—H13C | 109.5 |
N1—C2—H2B | 109.2 | H13A—C13—H13B | 109.5 |
N1—C2—C3 | 112.26 (12) | H13A—C13—H13C | 109.5 |
H2A—C2—H2B | 107.9 | H13B—C13—H13C | 109.5 |
C3—C2—H2A | 109.2 | C11—C14—H14A | 109.5 |
C3—C2—H2B | 109.2 | C11—C14—H14B | 109.5 |
C1—N2—C5 | 128.18 (11) | C11—C14—H14C | 109.5 |
C1—N2—C15 | 118.63 (11) | H14A—C14—H14B | 109.5 |
C15—N2—C5 | 113.15 (10) | H14A—C14—H14C | 109.5 |
C2—C3—H3A | 109.7 | H14B—C14—H14C | 109.5 |
C2—C3—H3B | 109.7 | C16—C15—N2 | 119.48 (12) |
C2—C3—C4 | 110.02 (12) | C20—C15—N2 | 118.55 (12) |
H3A—C3—H3B | 108.2 | C20—C15—C16 | 121.94 (13) |
C4—C3—H3A | 109.7 | C15—C16—C21 | 121.81 (12) |
C4—C3—H3B | 109.7 | C17—C16—C15 | 117.98 (13) |
C3—C4—H4A | 109.1 | C17—C16—C21 | 120.21 (13) |
C3—C4—H4B | 109.1 | C16—C17—H17 | 119.2 |
H4A—C4—H4B | 107.9 | C16—C17—C18 | 121.61 (13) |
C5—C4—C3 | 112.33 (12) | C18—C17—H17 | 119.2 |
C5—C4—H4A | 109.1 | C17—C18—C22 | 120.58 (14) |
C5—C4—H4B | 109.1 | C19—C18—C17 | 118.87 (13) |
N2—C5—C4 | 114.70 (11) | C19—C18—C22 | 120.55 (14) |
N2—C5—H5A | 108.6 | C18—C19—H19 | 119.2 |
N2—C5—H5B | 108.6 | C18—C19—C20 | 121.55 (14) |
C4—C5—H5A | 108.6 | C20—C19—H19 | 119.2 |
C4—C5—H5B | 108.6 | C15—C20—C23 | 121.55 (13) |
H5A—C5—H5B | 107.6 | C19—C20—C15 | 118.04 (13) |
C6—C7—C8 | 118.40 (13) | C19—C20—C23 | 120.38 (13) |
C6—C7—C12 | 121.52 (12) | C16—C21—H21A | 109.5 |
C8—C7—C12 | 120.07 (13) | C16—C21—H21B | 109.5 |
C7—C6—N1 | 118.99 (12) | C16—C21—H21C | 109.5 |
C7—C6—C11 | 121.35 (12) | H21A—C21—H21B | 109.5 |
C11—C6—N1 | 119.57 (12) | H21A—C21—H21C | 109.5 |
C8—C9—C10 | 118.20 (13) | H21B—C21—H21C | 109.5 |
C8—C9—C13 | 121.19 (14) | C18—C22—H22A | 109.5 |
C10—C9—C13 | 120.61 (14) | C18—C22—H22B | 109.5 |
C7—C8—H8 | 119.1 | C18—C22—H22C | 109.5 |
C9—C8—C7 | 121.75 (13) | H22A—C22—H22B | 109.5 |
C9—C8—H8 | 119.1 | H22A—C22—H22C | 109.5 |
C9—C10—H10 | 118.9 | H22B—C22—H22C | 109.5 |
C9—C10—C11 | 122.15 (13) | C20—C23—H23A | 109.5 |
C11—C10—H10 | 118.9 | C20—C23—H23B | 109.5 |
C6—C11—C14 | 121.68 (12) | C20—C23—H23C | 109.5 |
C10—C11—C6 | 118.12 (13) | H23A—C23—H23B | 109.5 |
C10—C11—C14 | 120.19 (13) | H23A—C23—H23C | 109.5 |
C7—C12—H12A | 109.5 | H23B—C23—H23C | 109.5 |
C7—C12—H12B | 109.5 | ||
S1—C1—N2—C5 | −160.74 (11) | C6—N1—C1—N2 | −172.91 (12) |
S1—C1—N2—C15 | 16.83 (17) | C6—N1—C2—C3 | 106.84 (13) |
N1—C1—N2—C5 | 20.1 (2) | C6—C7—C8—C9 | −0.4 (2) |
N1—C1—N2—C15 | −162.33 (12) | C9—C10—C11—C6 | −0.4 (2) |
N1—C2—C3—C4 | 49.58 (15) | C9—C10—C11—C14 | −179.36 (13) |
N1—C6—C11—C10 | 175.13 (12) | C8—C7—C6—N1 | −174.76 (12) |
N1—C6—C11—C14 | −6.0 (2) | C8—C7—C6—C11 | 1.7 (2) |
C1—N1—C2—C3 | −86.27 (15) | C8—C9—C10—C11 | 1.7 (2) |
C1—N1—C6—C7 | −96.59 (15) | C10—C9—C8—C7 | −1.3 (2) |
C1—N1—C6—C11 | 86.86 (16) | C12—C7—C6—N1 | 6.02 (19) |
C1—N2—C5—C4 | 24.2 (2) | C12—C7—C6—C11 | −177.50 (13) |
C1—N2—C15—C16 | −101.69 (15) | C12—C7—C8—C9 | 178.86 (13) |
C1—N2—C15—C20 | 80.59 (16) | C13—C9—C8—C7 | 177.75 (14) |
C2—N1—C1—S1 | −158.36 (10) | C13—C9—C10—C11 | −177.34 (14) |
C2—N1—C1—N2 | 20.80 (19) | C15—N2—C5—C4 | −153.50 (12) |
C2—N1—C6—C7 | 70.48 (16) | C15—C16—C17—C18 | 0.6 (2) |
C2—N1—C6—C11 | −106.07 (15) | C16—C15—C20—C19 | −0.7 (2) |
C2—C3—C4—C5 | 36.75 (16) | C16—C15—C20—C23 | 177.42 (13) |
N2—C15—C16—C17 | −177.21 (11) | C16—C17—C18—C19 | −1.3 (2) |
N2—C15—C16—C21 | 3.45 (19) | C16—C17—C18—C22 | 178.76 (14) |
N2—C15—C20—C19 | 176.91 (12) | C17—C18—C19—C20 | 1.0 (2) |
N2—C15—C20—C23 | −4.93 (19) | C18—C19—C20—C15 | 0.0 (2) |
C3—C4—C5—N2 | −79.12 (15) | C18—C19—C20—C23 | −178.16 (13) |
C5—N2—C15—C16 | 76.22 (15) | C20—C15—C16—C17 | 0.4 (2) |
C5—N2—C15—C20 | −101.49 (14) | C20—C15—C16—C21 | −178.91 (12) |
C7—C6—C11—C10 | −1.3 (2) | C21—C16—C17—C18 | 179.97 (13) |
C7—C6—C11—C14 | 177.58 (13) | C22—C18—C19—C20 | −179.09 (14) |
C6—N1—C1—S1 | 7.93 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3B···S1i | 0.99 | 3.01 | 3.7030 (15) | 128 |
C5—H5A···S1i | 0.99 | 2.87 | 3.4858 (14) | 121 |
Symmetry code: (i) x, −y+3/2, z+1/2. |
C23H30N2Se | Dx = 1.332 Mg m−3 |
Mr = 413.45 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbca | Cell parameters from 9854 reflections |
a = 17.4279 (4) Å | θ = 2.2–27.1° |
b = 15.2522 (4) Å | µ = 1.83 mm−1 |
c = 31.0253 (7) Å | T = 100 K |
V = 8247.0 (3) Å3 | Block, colourless |
Z = 16 | 0.08 × 0.07 × 0.07 mm |
F(000) = 3456 |
Bruker D8 Venture Photon 2 diffractometer | 7294 reflections with I > 2σ(I) |
Radiation source: Incoatec IµS | Rint = 0.072 |
φ and ω scans | θmax = 27.1°, θmin = 2.2° |
Absorption correction: multi-scan SADABS v2016/2 (Bruker AXS Inc., 2017) | h = −22→22 |
Tmin = 0.697, Tmax = 0.746 | k = −19→19 |
72880 measured reflections | l = −39→36 |
9109 independent reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.078 | H-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 parameters | Δρmax = 0.39 e Å−3 |
0 restraints | Δρmin = −0.33 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
Se1 | 0.24756 (2) | 0.41747 (2) | 0.61765 (2) | 0.01788 (6) | |
N1 | 0.27122 (10) | 0.59242 (11) | 0.64196 (6) | 0.0143 (4) | |
N2 | 0.37745 (10) | 0.52283 (11) | 0.61141 (6) | 0.0138 (4) | |
C1 | 0.30350 (12) | 0.51984 (13) | 0.62404 (7) | 0.0128 (4) | |
C2 | 0.29679 (14) | 0.68578 (14) | 0.63787 (8) | 0.0204 (5) | |
H2A | 0.327269 | 0.701351 | 0.663691 | 0.024* | |
H2B | 0.250851 | 0.723944 | 0.637512 | 0.024* | |
C3 | 0.34430 (14) | 0.70498 (15) | 0.59812 (8) | 0.0221 (5) | |
H3A | 0.343938 | 0.768926 | 0.592654 | 0.027* | |
H3B | 0.320547 | 0.675730 | 0.572954 | 0.027* | |
C4 | 0.42728 (13) | 0.67393 (15) | 0.60253 (9) | 0.0238 (5) | |
H4A | 0.449508 | 0.664614 | 0.573528 | 0.029* | |
H4B | 0.457907 | 0.719634 | 0.617276 | 0.029* | |
C5 | 0.43137 (13) | 0.58965 (15) | 0.62790 (8) | 0.0187 (5) | |
H5A | 0.484289 | 0.566240 | 0.626511 | 0.022* | |
H5B | 0.419360 | 0.601968 | 0.658497 | 0.022* | |
C6 | 0.20033 (12) | 0.58361 (14) | 0.66556 (7) | 0.0145 (4) | |
C7 | 0.13045 (13) | 0.60225 (14) | 0.64548 (7) | 0.0172 (5) | |
C8 | 0.06369 (13) | 0.59627 (15) | 0.66997 (8) | 0.0200 (5) | |
H8 | 0.015787 | 0.607763 | 0.656497 | 0.024* | |
C9 | 0.06462 (14) | 0.57420 (15) | 0.71320 (8) | 0.0212 (5) | |
C10 | 0.13509 (15) | 0.55836 (16) | 0.73235 (8) | 0.0227 (5) | |
H10 | 0.136642 | 0.543746 | 0.762105 | 0.027* | |
C11 | 0.20354 (13) | 0.56311 (15) | 0.70954 (7) | 0.0183 (5) | |
C12 | 0.12753 (15) | 0.62679 (18) | 0.59865 (8) | 0.0270 (6) | |
H12A | 0.076094 | 0.614956 | 0.587289 | 0.041* | |
H12B | 0.165340 | 0.592139 | 0.582642 | 0.041* | |
H12C | 0.139241 | 0.689297 | 0.595461 | 0.041* | |
C13 | −0.00917 (15) | 0.56505 (17) | 0.73841 (9) | 0.0315 (6) | |
H13A | −0.050010 | 0.597953 | 0.723927 | 0.047* | |
H13B | −0.001831 | 0.588237 | 0.767578 | 0.047* | |
H13C | −0.023512 | 0.503008 | 0.740068 | 0.047* | |
C14 | 0.27916 (15) | 0.54467 (19) | 0.73116 (8) | 0.0301 (6) | |
H14A | 0.272270 | 0.545175 | 0.762508 | 0.045* | |
H14B | 0.316431 | 0.589797 | 0.722959 | 0.045* | |
H14C | 0.298022 | 0.487018 | 0.722085 | 0.045* | |
C15 | 0.41106 (12) | 0.45437 (13) | 0.58528 (7) | 0.0137 (4) | |
C16 | 0.40346 (12) | 0.45655 (14) | 0.54064 (7) | 0.0150 (4) | |
C17 | 0.43903 (13) | 0.39130 (15) | 0.51629 (8) | 0.0177 (5) | |
H17 | 0.434344 | 0.392502 | 0.485785 | 0.021* | |
C18 | 0.48113 (12) | 0.32459 (15) | 0.53552 (7) | 0.0172 (4) | |
C19 | 0.48825 (12) | 0.32494 (14) | 0.58018 (7) | 0.0173 (5) | |
H19 | 0.517563 | 0.280194 | 0.593692 | 0.021* | |
C20 | 0.45381 (13) | 0.38870 (15) | 0.60559 (7) | 0.0164 (5) | |
C21 | 0.35540 (14) | 0.52488 (15) | 0.51794 (7) | 0.0204 (5) | |
H21A | 0.304510 | 0.527578 | 0.531307 | 0.031* | |
H21B | 0.350099 | 0.509166 | 0.487456 | 0.031* | |
H21C | 0.380433 | 0.582211 | 0.520332 | 0.031* | |
C22 | 0.51597 (15) | 0.25184 (16) | 0.50905 (8) | 0.0239 (5) | |
H22A | 0.571760 | 0.259461 | 0.507823 | 0.036* | |
H22B | 0.494851 | 0.253584 | 0.479789 | 0.036* | |
H22C | 0.503932 | 0.195193 | 0.522340 | 0.036* | |
C23 | 0.45985 (15) | 0.38390 (17) | 0.65411 (8) | 0.0269 (6) | |
H23A | 0.481764 | 0.327216 | 0.662465 | 0.040* | |
H23B | 0.408672 | 0.390103 | 0.666838 | 0.040* | |
H23C | 0.493036 | 0.431265 | 0.664509 | 0.040* | |
Se2 | 0.36720 (2) | 0.32364 (2) | 0.37637 (2) | 0.01701 (6) | |
N3 | 0.26364 (10) | 0.19889 (11) | 0.40670 (6) | 0.0127 (4) | |
N4 | 0.34705 (10) | 0.14818 (11) | 0.35318 (6) | 0.0132 (4) | |
C24 | 0.32192 (12) | 0.21407 (13) | 0.37873 (7) | 0.0126 (4) | |
C25 | 0.24357 (14) | 0.10973 (14) | 0.42179 (7) | 0.0176 (5) | |
H25A | 0.218801 | 0.114125 | 0.450422 | 0.021* | |
H25B | 0.291279 | 0.075204 | 0.425249 | 0.021* | |
C26 | 0.19040 (14) | 0.06168 (15) | 0.39144 (8) | 0.0214 (5) | |
H26A | 0.138654 | 0.088325 | 0.392685 | 0.026* | |
H26B | 0.186012 | −0.000385 | 0.400452 | 0.026* | |
C27 | 0.22096 (14) | 0.06627 (16) | 0.34535 (8) | 0.0219 (5) | |
H27A | 0.199879 | 0.016535 | 0.328610 | 0.026* | |
H27B | 0.202784 | 0.121191 | 0.331740 | 0.026* | |
C28 | 0.30788 (13) | 0.06338 (15) | 0.34332 (8) | 0.0200 (5) | |
H28A | 0.326324 | 0.018512 | 0.363918 | 0.024* | |
H28B | 0.323294 | 0.044343 | 0.314064 | 0.024* | |
C29 | 0.22759 (12) | 0.27116 (13) | 0.42915 (7) | 0.0129 (4) | |
C30 | 0.24624 (13) | 0.28639 (14) | 0.47206 (7) | 0.0151 (4) | |
C31 | 0.20980 (13) | 0.35541 (15) | 0.49346 (7) | 0.0175 (5) | |
H31 | 0.222695 | 0.367262 | 0.522634 | 0.021* | |
C32 | 0.15514 (13) | 0.40709 (14) | 0.47306 (8) | 0.0188 (5) | |
C33 | 0.13732 (13) | 0.38895 (14) | 0.43025 (7) | 0.0178 (5) | |
H33 | 0.099708 | 0.423660 | 0.416105 | 0.021* | |
C34 | 0.17286 (12) | 0.32151 (14) | 0.40748 (7) | 0.0146 (4) | |
C35 | 0.30545 (14) | 0.23231 (16) | 0.49537 (8) | 0.0229 (5) | |
H35A | 0.282157 | 0.177285 | 0.505110 | 0.034* | |
H35B | 0.324559 | 0.265048 | 0.520338 | 0.034* | |
H35C | 0.348155 | 0.219400 | 0.475826 | 0.034* | |
C36 | 0.11402 (15) | 0.47840 (16) | 0.49765 (9) | 0.0272 (6) | |
H36A | 0.091077 | 0.519918 | 0.477284 | 0.041* | |
H36B | 0.150684 | 0.509297 | 0.516172 | 0.041* | |
H36C | 0.073616 | 0.452268 | 0.515473 | 0.041* | |
C37 | 0.15406 (13) | 0.30592 (15) | 0.36075 (7) | 0.0193 (5) | |
H37A | 0.113906 | 0.346878 | 0.351613 | 0.029* | |
H37B | 0.135889 | 0.245593 | 0.356992 | 0.029* | |
H37C | 0.200142 | 0.315125 | 0.343225 | 0.029* | |
C38 | 0.41706 (12) | 0.15949 (13) | 0.32882 (7) | 0.0139 (4) | |
C39 | 0.48655 (13) | 0.13351 (13) | 0.34659 (7) | 0.0142 (4) | |
C40 | 0.55311 (13) | 0.14136 (15) | 0.32181 (8) | 0.0187 (5) | |
H40 | 0.600806 | 0.122810 | 0.333495 | 0.022* | |
C41 | 0.55078 (13) | 0.17592 (15) | 0.28026 (8) | 0.0200 (5) | |
C42 | 0.47984 (14) | 0.20091 (15) | 0.26341 (7) | 0.0197 (5) | |
H42 | 0.477836 | 0.224709 | 0.235132 | 0.024* | |
C43 | 0.41222 (13) | 0.19218 (14) | 0.28649 (7) | 0.0162 (5) | |
C44 | 0.49173 (14) | 0.09976 (15) | 0.39223 (7) | 0.0197 (5) | |
H44A | 0.477852 | 0.146695 | 0.412342 | 0.029* | |
H44B | 0.544301 | 0.080328 | 0.398097 | 0.029* | |
H44C | 0.456397 | 0.050325 | 0.395882 | 0.029* | |
C45 | 0.62329 (15) | 0.18428 (18) | 0.25400 (9) | 0.0309 (6) | |
H45A | 0.617548 | 0.151658 | 0.226983 | 0.046* | |
H45B | 0.666578 | 0.160362 | 0.270386 | 0.046* | |
H45C | 0.632851 | 0.246239 | 0.247595 | 0.046* | |
C46 | 0.33635 (14) | 0.21877 (16) | 0.26720 (8) | 0.0234 (5) | |
H46A | 0.344789 | 0.243312 | 0.238394 | 0.035* | |
H46B | 0.312021 | 0.262979 | 0.285600 | 0.035* | |
H46C | 0.302904 | 0.167302 | 0.265054 | 0.035* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Se1 | 0.01492 (11) | 0.01341 (11) | 0.02531 (12) | −0.00392 (8) | 0.00470 (10) | −0.00215 (9) |
N1 | 0.0126 (9) | 0.0128 (9) | 0.0176 (9) | −0.0016 (7) | 0.0028 (7) | −0.0002 (7) |
N2 | 0.0118 (9) | 0.0123 (9) | 0.0175 (9) | −0.0008 (7) | −0.0010 (7) | −0.0003 (7) |
C1 | 0.0146 (10) | 0.0121 (10) | 0.0117 (10) | −0.0003 (8) | −0.0002 (8) | 0.0030 (8) |
C2 | 0.0213 (12) | 0.0113 (11) | 0.0285 (13) | −0.0006 (9) | 0.0037 (10) | −0.0007 (9) |
C3 | 0.0227 (12) | 0.0133 (11) | 0.0303 (13) | −0.0027 (9) | 0.0051 (10) | 0.0040 (10) |
C4 | 0.0184 (12) | 0.0167 (11) | 0.0362 (14) | −0.0065 (9) | 0.0047 (10) | −0.0020 (11) |
C5 | 0.0121 (10) | 0.0195 (11) | 0.0246 (12) | −0.0023 (9) | −0.0030 (9) | −0.0046 (10) |
C6 | 0.0137 (11) | 0.0134 (10) | 0.0163 (11) | 0.0005 (8) | 0.0020 (9) | 0.0014 (9) |
C7 | 0.0184 (11) | 0.0155 (11) | 0.0176 (11) | 0.0036 (9) | −0.0003 (9) | −0.0005 (9) |
C8 | 0.0155 (11) | 0.0192 (12) | 0.0252 (13) | 0.0039 (9) | 0.0009 (10) | −0.0015 (10) |
C9 | 0.0203 (12) | 0.0161 (11) | 0.0272 (13) | 0.0007 (9) | 0.0076 (10) | −0.0023 (10) |
C10 | 0.0297 (14) | 0.0228 (12) | 0.0155 (11) | 0.0010 (10) | 0.0053 (10) | 0.0025 (9) |
C11 | 0.0197 (12) | 0.0165 (11) | 0.0187 (12) | 0.0007 (9) | −0.0005 (9) | 0.0000 (9) |
C12 | 0.0229 (13) | 0.0377 (15) | 0.0206 (12) | 0.0080 (11) | −0.0019 (11) | 0.0033 (11) |
C13 | 0.0275 (14) | 0.0296 (14) | 0.0375 (16) | 0.0020 (11) | 0.0176 (12) | 0.0018 (12) |
C14 | 0.0242 (14) | 0.0461 (17) | 0.0200 (13) | 0.0047 (12) | −0.0040 (11) | 0.0062 (12) |
C15 | 0.0102 (10) | 0.0117 (10) | 0.0192 (11) | −0.0005 (8) | 0.0017 (9) | −0.0002 (9) |
C16 | 0.0108 (10) | 0.0152 (11) | 0.0189 (11) | −0.0006 (8) | −0.0003 (9) | 0.0054 (9) |
C17 | 0.0156 (11) | 0.0188 (11) | 0.0188 (11) | 0.0010 (9) | 0.0020 (9) | 0.0034 (9) |
C18 | 0.0133 (10) | 0.0170 (11) | 0.0214 (11) | −0.0001 (9) | 0.0044 (9) | 0.0017 (9) |
C19 | 0.0136 (10) | 0.0163 (11) | 0.0220 (11) | 0.0040 (9) | −0.0016 (9) | 0.0050 (9) |
C20 | 0.0148 (11) | 0.0187 (11) | 0.0158 (11) | 0.0000 (9) | −0.0017 (9) | 0.0036 (9) |
C21 | 0.0233 (12) | 0.0195 (11) | 0.0185 (11) | 0.0068 (10) | −0.0018 (10) | 0.0035 (9) |
C22 | 0.0268 (13) | 0.0216 (12) | 0.0234 (13) | 0.0079 (10) | 0.0047 (10) | 0.0015 (10) |
C23 | 0.0314 (14) | 0.0307 (14) | 0.0188 (12) | 0.0123 (11) | −0.0028 (11) | 0.0036 (10) |
Se2 | 0.01419 (11) | 0.01075 (10) | 0.02608 (12) | −0.00273 (8) | 0.00550 (9) | −0.00285 (9) |
N3 | 0.0130 (9) | 0.0098 (8) | 0.0153 (9) | −0.0005 (7) | 0.0014 (7) | −0.0003 (7) |
N4 | 0.0121 (9) | 0.0111 (8) | 0.0166 (9) | −0.0023 (7) | 0.0014 (7) | −0.0033 (7) |
C24 | 0.0115 (10) | 0.0119 (10) | 0.0144 (10) | 0.0016 (8) | −0.0034 (9) | −0.0003 (8) |
C25 | 0.0238 (12) | 0.0103 (10) | 0.0187 (11) | −0.0030 (9) | 0.0035 (10) | 0.0012 (8) |
C26 | 0.0215 (12) | 0.0163 (11) | 0.0263 (13) | −0.0061 (9) | 0.0044 (10) | −0.0021 (10) |
C27 | 0.0190 (12) | 0.0231 (12) | 0.0235 (13) | −0.0073 (9) | −0.0016 (10) | −0.0058 (10) |
C28 | 0.0206 (12) | 0.0170 (11) | 0.0222 (12) | −0.0026 (9) | 0.0018 (10) | −0.0072 (9) |
C29 | 0.0113 (10) | 0.0101 (10) | 0.0172 (11) | −0.0014 (8) | 0.0022 (8) | −0.0015 (8) |
C30 | 0.0134 (10) | 0.0155 (11) | 0.0164 (10) | −0.0055 (9) | 0.0020 (9) | −0.0003 (8) |
C31 | 0.0174 (11) | 0.0184 (11) | 0.0165 (11) | −0.0064 (9) | 0.0012 (9) | −0.0035 (9) |
C32 | 0.0177 (11) | 0.0129 (10) | 0.0257 (12) | −0.0032 (9) | 0.0087 (10) | −0.0024 (9) |
C33 | 0.0128 (11) | 0.0170 (11) | 0.0235 (12) | 0.0013 (9) | 0.0055 (9) | 0.0026 (9) |
C34 | 0.0115 (10) | 0.0145 (10) | 0.0178 (11) | −0.0030 (8) | 0.0037 (8) | 0.0007 (9) |
C35 | 0.0226 (13) | 0.0242 (13) | 0.0219 (12) | 0.0000 (10) | −0.0056 (10) | −0.0003 (10) |
C36 | 0.0278 (14) | 0.0213 (12) | 0.0326 (14) | 0.0005 (10) | 0.0114 (11) | −0.0071 (11) |
C37 | 0.0159 (11) | 0.0243 (12) | 0.0176 (11) | 0.0037 (9) | −0.0019 (9) | 0.0004 (9) |
C38 | 0.0140 (10) | 0.0106 (10) | 0.0172 (11) | −0.0002 (8) | 0.0033 (9) | −0.0047 (8) |
C39 | 0.0174 (11) | 0.0109 (10) | 0.0143 (10) | 0.0004 (8) | −0.0004 (9) | −0.0032 (8) |
C40 | 0.0165 (11) | 0.0184 (11) | 0.0211 (12) | 0.0024 (9) | 0.0008 (9) | −0.0044 (9) |
C41 | 0.0191 (12) | 0.0194 (11) | 0.0214 (12) | −0.0014 (10) | 0.0060 (9) | −0.0071 (10) |
C42 | 0.0269 (13) | 0.0191 (11) | 0.0131 (11) | −0.0016 (10) | 0.0026 (10) | −0.0014 (9) |
C43 | 0.0192 (11) | 0.0117 (11) | 0.0176 (11) | 0.0002 (8) | −0.0005 (9) | −0.0025 (8) |
C44 | 0.0214 (12) | 0.0195 (12) | 0.0181 (11) | −0.0006 (9) | −0.0021 (9) | 0.0008 (9) |
C45 | 0.0255 (13) | 0.0373 (15) | 0.0298 (14) | −0.0017 (12) | 0.0127 (11) | −0.0022 (12) |
C46 | 0.0196 (12) | 0.0263 (13) | 0.0243 (13) | 0.0023 (10) | −0.0050 (10) | 0.0040 (10) |
Se1—C1 | 1.851 (2) | Se2—C24 | 1.849 (2) |
N1—C1 | 1.360 (3) | N3—C24 | 1.356 (3) |
N1—C2 | 1.498 (3) | N3—C25 | 1.480 (3) |
N1—C6 | 1.442 (3) | N3—C29 | 1.447 (3) |
N2—C1 | 1.348 (3) | N4—C24 | 1.353 (3) |
N2—C5 | 1.478 (3) | N4—C28 | 1.494 (3) |
N2—C15 | 1.446 (3) | N4—C38 | 1.446 (3) |
C2—H2A | 0.9900 | C25—H25A | 0.9900 |
C2—H2B | 0.9900 | C25—H25B | 0.9900 |
C2—C3 | 1.514 (3) | C25—C26 | 1.511 (3) |
C3—H3A | 0.9900 | C26—H26A | 0.9900 |
C3—H3B | 0.9900 | C26—H26B | 0.9900 |
C3—C4 | 1.528 (3) | C26—C27 | 1.528 (3) |
C4—H4A | 0.9900 | C27—H27A | 0.9900 |
C4—H4B | 0.9900 | C27—H27B | 0.9900 |
C4—C5 | 1.509 (3) | C27—C28 | 1.517 (3) |
C5—H5A | 0.9900 | C28—H28A | 0.9900 |
C5—H5B | 0.9900 | C28—H28B | 0.9900 |
C6—C7 | 1.397 (3) | C29—C30 | 1.390 (3) |
C6—C11 | 1.401 (3) | C29—C34 | 1.397 (3) |
C7—C8 | 1.393 (3) | C30—C31 | 1.397 (3) |
C7—C12 | 1.501 (3) | C30—C35 | 1.506 (3) |
C8—H8 | 0.9500 | C31—H31 | 0.9500 |
C8—C9 | 1.383 (3) | C31—C32 | 1.389 (3) |
C9—C10 | 1.385 (3) | C32—C33 | 1.392 (3) |
C9—C13 | 1.512 (3) | C32—C36 | 1.509 (3) |
C10—H10 | 0.9500 | C33—H33 | 0.9500 |
C10—C11 | 1.389 (3) | C33—C34 | 1.393 (3) |
C11—C14 | 1.505 (3) | C34—C37 | 1.505 (3) |
C12—H12A | 0.9800 | C35—H35A | 0.9800 |
C12—H12B | 0.9800 | C35—H35B | 0.9800 |
C12—H12C | 0.9800 | C35—H35C | 0.9800 |
C13—H13A | 0.9800 | C36—H36A | 0.9800 |
C13—H13B | 0.9800 | C36—H36B | 0.9800 |
C13—H13C | 0.9800 | C36—H36C | 0.9800 |
C14—H14A | 0.9800 | C37—H37A | 0.9800 |
C14—H14B | 0.9800 | C37—H37B | 0.9800 |
C14—H14C | 0.9800 | C37—H37C | 0.9800 |
C15—C16 | 1.392 (3) | C38—C39 | 1.388 (3) |
C15—C20 | 1.398 (3) | C38—C43 | 1.407 (3) |
C16—C17 | 1.395 (3) | C39—C40 | 1.397 (3) |
C16—C21 | 1.511 (3) | C39—C44 | 1.509 (3) |
C17—H17 | 0.9500 | C40—H40 | 0.9500 |
C17—C18 | 1.389 (3) | C40—C41 | 1.393 (3) |
C18—C19 | 1.391 (3) | C41—C42 | 1.395 (3) |
C18—C22 | 1.508 (3) | C41—C45 | 1.509 (3) |
C19—H19 | 0.9500 | C42—H42 | 0.9500 |
C19—C20 | 1.388 (3) | C42—C43 | 1.385 (3) |
C20—C23 | 1.511 (3) | C43—C46 | 1.507 (3) |
C21—H21A | 0.9800 | C44—H44A | 0.9800 |
C21—H21B | 0.9800 | C44—H44B | 0.9800 |
C21—H21C | 0.9800 | C44—H44C | 0.9800 |
C22—H22A | 0.9800 | C45—H45A | 0.9800 |
C22—H22B | 0.9800 | C45—H45B | 0.9800 |
C22—H22C | 0.9800 | C45—H45C | 0.9800 |
C23—H23A | 0.9800 | C46—H46A | 0.9800 |
C23—H23B | 0.9800 | C46—H46B | 0.9800 |
C23—H23C | 0.9800 | C46—H46C | 0.9800 |
C1—N1—C2 | 128.02 (18) | C24—N3—C25 | 122.43 (17) |
C1—N1—C6 | 119.07 (17) | C24—N3—C29 | 120.21 (17) |
C6—N1—C2 | 112.73 (17) | C29—N3—C25 | 116.43 (17) |
C1—N2—C5 | 122.05 (18) | C24—N4—C28 | 127.97 (18) |
C1—N2—C15 | 121.73 (18) | C24—N4—C38 | 119.40 (17) |
C15—N2—C5 | 115.77 (17) | C38—N4—C28 | 112.45 (17) |
N1—C1—Se1 | 120.80 (15) | N3—C24—Se2 | 119.94 (15) |
N2—C1—Se1 | 120.06 (15) | N4—C24—Se2 | 120.67 (16) |
N2—C1—N1 | 119.13 (18) | N4—C24—N3 | 119.39 (18) |
N1—C2—H2A | 108.6 | N3—C25—H25A | 108.9 |
N1—C2—H2B | 108.6 | N3—C25—H25B | 108.9 |
N1—C2—C3 | 114.56 (19) | N3—C25—C26 | 113.18 (18) |
H2A—C2—H2B | 107.6 | H25A—C25—H25B | 107.8 |
C3—C2—H2A | 108.6 | C26—C25—H25A | 108.9 |
C3—C2—H2B | 108.6 | C26—C25—H25B | 108.9 |
C2—C3—H3A | 109.1 | C25—C26—H26A | 109.6 |
C2—C3—H3B | 109.1 | C25—C26—H26B | 109.6 |
C2—C3—C4 | 112.6 (2) | C25—C26—C27 | 110.33 (19) |
H3A—C3—H3B | 107.8 | H26A—C26—H26B | 108.1 |
C4—C3—H3A | 109.1 | C27—C26—H26A | 109.6 |
C4—C3—H3B | 109.1 | C27—C26—H26B | 109.6 |
C3—C4—H4A | 109.5 | C26—C27—H27A | 109.1 |
C3—C4—H4B | 109.5 | C26—C27—H27B | 109.1 |
H4A—C4—H4B | 108.1 | H27A—C27—H27B | 107.8 |
C5—C4—C3 | 110.82 (19) | C28—C27—C26 | 112.7 (2) |
C5—C4—H4A | 109.5 | C28—C27—H27A | 109.1 |
C5—C4—H4B | 109.5 | C28—C27—H27B | 109.1 |
N2—C5—C4 | 112.15 (19) | N4—C28—C27 | 115.00 (19) |
N2—C5—H5A | 109.2 | N4—C28—H28A | 108.5 |
N2—C5—H5B | 109.2 | N4—C28—H28B | 108.5 |
C4—C5—H5A | 109.2 | C27—C28—H28A | 108.5 |
C4—C5—H5B | 109.2 | C27—C28—H28B | 108.5 |
H5A—C5—H5B | 107.9 | H28A—C28—H28B | 107.5 |
C7—C6—N1 | 120.07 (19) | C30—C29—N3 | 119.11 (19) |
C7—C6—C11 | 121.0 (2) | C30—C29—C34 | 121.9 (2) |
C11—C6—N1 | 118.76 (19) | C34—C29—N3 | 118.92 (19) |
C6—C7—C12 | 120.8 (2) | C29—C30—C31 | 118.3 (2) |
C8—C7—C6 | 118.1 (2) | C29—C30—C35 | 121.9 (2) |
C8—C7—C12 | 121.1 (2) | C31—C30—C35 | 119.7 (2) |
C7—C8—H8 | 118.8 | C30—C31—H31 | 119.2 |
C9—C8—C7 | 122.4 (2) | C32—C31—C30 | 121.5 (2) |
C9—C8—H8 | 118.8 | C32—C31—H31 | 119.2 |
C8—C9—C10 | 118.0 (2) | C31—C32—C33 | 118.4 (2) |
C8—C9—C13 | 121.0 (2) | C31—C32—C36 | 120.3 (2) |
C10—C9—C13 | 121.1 (2) | C33—C32—C36 | 121.3 (2) |
C9—C10—H10 | 118.9 | C32—C33—H33 | 118.9 |
C9—C10—C11 | 122.3 (2) | C32—C33—C34 | 122.1 (2) |
C11—C10—H10 | 118.9 | C34—C33—H33 | 118.9 |
C6—C11—C14 | 120.7 (2) | C29—C34—C37 | 121.69 (19) |
C10—C11—C6 | 118.3 (2) | C33—C34—C29 | 117.7 (2) |
C10—C11—C14 | 121.0 (2) | C33—C34—C37 | 120.5 (2) |
C7—C12—H12A | 109.5 | C30—C35—H35A | 109.5 |
C7—C12—H12B | 109.5 | C30—C35—H35B | 109.5 |
C7—C12—H12C | 109.5 | C30—C35—H35C | 109.5 |
H12A—C12—H12B | 109.5 | H35A—C35—H35B | 109.5 |
H12A—C12—H12C | 109.5 | H35A—C35—H35C | 109.5 |
H12B—C12—H12C | 109.5 | H35B—C35—H35C | 109.5 |
C9—C13—H13A | 109.5 | C32—C36—H36A | 109.5 |
C9—C13—H13B | 109.5 | C32—C36—H36B | 109.5 |
C9—C13—H13C | 109.5 | C32—C36—H36C | 109.5 |
H13A—C13—H13B | 109.5 | H36A—C36—H36B | 109.5 |
H13A—C13—H13C | 109.5 | H36A—C36—H36C | 109.5 |
H13B—C13—H13C | 109.5 | H36B—C36—H36C | 109.5 |
C11—C14—H14A | 109.5 | C34—C37—H37A | 109.5 |
C11—C14—H14B | 109.5 | C34—C37—H37B | 109.5 |
C11—C14—H14C | 109.5 | C34—C37—H37C | 109.5 |
H14A—C14—H14B | 109.5 | H37A—C37—H37B | 109.5 |
H14A—C14—H14C | 109.5 | H37A—C37—H37C | 109.5 |
H14B—C14—H14C | 109.5 | H37B—C37—H37C | 109.5 |
C16—C15—N2 | 120.15 (19) | C39—C38—N4 | 119.64 (19) |
C16—C15—C20 | 121.1 (2) | C39—C38—C43 | 121.6 (2) |
C20—C15—N2 | 118.72 (19) | C43—C38—N4 | 118.66 (19) |
C15—C16—C17 | 118.7 (2) | C38—C39—C40 | 118.8 (2) |
C15—C16—C21 | 122.2 (2) | C38—C39—C44 | 121.5 (2) |
C17—C16—C21 | 119.1 (2) | C40—C39—C44 | 119.7 (2) |
C16—C17—H17 | 119.2 | C39—C40—H40 | 119.4 |
C18—C17—C16 | 121.6 (2) | C41—C40—C39 | 121.2 (2) |
C18—C17—H17 | 119.2 | C41—C40—H40 | 119.4 |
C17—C18—C19 | 118.2 (2) | C40—C41—C42 | 118.4 (2) |
C17—C18—C22 | 121.2 (2) | C40—C41—C45 | 120.5 (2) |
C19—C18—C22 | 120.6 (2) | C42—C41—C45 | 121.1 (2) |
C18—C19—H19 | 119.0 | C41—C42—H42 | 118.9 |
C20—C19—C18 | 122.0 (2) | C43—C42—C41 | 122.3 (2) |
C20—C19—H19 | 119.0 | C43—C42—H42 | 118.9 |
C15—C20—C23 | 121.4 (2) | C38—C43—C46 | 121.2 (2) |
C19—C20—C15 | 118.4 (2) | C42—C43—C38 | 117.7 (2) |
C19—C20—C23 | 120.1 (2) | C42—C43—C46 | 121.0 (2) |
C16—C21—H21A | 109.5 | C39—C44—H44A | 109.5 |
C16—C21—H21B | 109.5 | C39—C44—H44B | 109.5 |
C16—C21—H21C | 109.5 | C39—C44—H44C | 109.5 |
H21A—C21—H21B | 109.5 | H44A—C44—H44B | 109.5 |
H21A—C21—H21C | 109.5 | H44A—C44—H44C | 109.5 |
H21B—C21—H21C | 109.5 | H44B—C44—H44C | 109.5 |
C18—C22—H22A | 109.5 | C41—C45—H45A | 109.5 |
C18—C22—H22B | 109.5 | C41—C45—H45B | 109.5 |
C18—C22—H22C | 109.5 | C41—C45—H45C | 109.5 |
H22A—C22—H22B | 109.5 | H45A—C45—H45B | 109.5 |
H22A—C22—H22C | 109.5 | H45A—C45—H45C | 109.5 |
H22B—C22—H22C | 109.5 | H45B—C45—H45C | 109.5 |
C20—C23—H23A | 109.5 | C43—C46—H46A | 109.5 |
C20—C23—H23B | 109.5 | C43—C46—H46B | 109.5 |
C20—C23—H23C | 109.5 | C43—C46—H46C | 109.5 |
H23A—C23—H23B | 109.5 | H46A—C46—H46B | 109.5 |
H23A—C23—H23C | 109.5 | H46A—C46—H46C | 109.5 |
H23B—C23—H23C | 109.5 | H46B—C46—H46C | 109.5 |
N1—C2—C3—C4 | −77.6 (3) | N3—C25—C26—C27 | 49.7 (3) |
N1—C6—C7—C8 | −177.5 (2) | N3—C29—C30—C31 | −178.80 (19) |
N1—C6—C7—C12 | 3.4 (3) | N3—C29—C30—C35 | 2.7 (3) |
N1—C6—C11—C10 | 177.4 (2) | N3—C29—C34—C33 | 178.04 (18) |
N1—C6—C11—C14 | −4.0 (3) | N3—C29—C34—C37 | −3.7 (3) |
N2—C15—C16—C17 | 177.61 (19) | N4—C38—C39—C40 | 177.18 (19) |
N2—C15—C16—C21 | −5.0 (3) | N4—C38—C39—C44 | −4.6 (3) |
N2—C15—C20—C19 | −177.70 (19) | N4—C38—C43—C42 | −178.76 (19) |
N2—C15—C20—C23 | 5.1 (3) | N4—C38—C43—C46 | 2.6 (3) |
C1—N1—C2—C3 | 23.4 (3) | C24—N3—C25—C26 | −85.0 (3) |
C1—N1—C6—C7 | −97.6 (2) | C24—N3—C29—C30 | −102.6 (2) |
C1—N1—C6—C11 | 87.5 (3) | C24—N3—C29—C34 | 79.8 (3) |
C1—N2—C5—C4 | −85.3 (3) | C24—N4—C28—C27 | 28.3 (3) |
C1—N2—C15—C16 | 84.9 (3) | C24—N4—C38—C39 | 91.4 (2) |
C1—N2—C15—C20 | −97.8 (2) | C24—N4—C38—C43 | −92.1 (2) |
C2—N1—C1—Se1 | −159.59 (18) | C25—N3—C24—Se2 | −157.52 (16) |
C2—N1—C1—N2 | 21.3 (3) | C25—N3—C24—N4 | 21.6 (3) |
C2—N1—C6—C7 | 78.0 (3) | C25—N3—C29—C30 | 66.6 (3) |
C2—N1—C6—C11 | −96.9 (2) | C25—N3—C29—C34 | −111.0 (2) |
C2—C3—C4—C5 | 35.7 (3) | C25—C26—C27—C28 | 35.3 (3) |
C3—C4—C5—N2 | 50.3 (3) | C26—C27—C28—N4 | −79.3 (3) |
C5—N2—C1—Se1 | −159.66 (16) | C28—N4—C24—Se2 | −165.05 (17) |
C5—N2—C1—N1 | 19.5 (3) | C28—N4—C24—N3 | 15.9 (3) |
C5—N2—C15—C16 | −102.6 (2) | C28—N4—C38—C39 | −93.1 (2) |
C5—N2—C15—C20 | 74.6 (2) | C28—N4—C38—C43 | 83.3 (2) |
C6—N1—C1—Se1 | 15.3 (3) | C29—N3—C24—Se2 | 11.0 (3) |
C6—N1—C1—N2 | −163.81 (19) | C29—N3—C24—N4 | −169.90 (19) |
C6—N1—C2—C3 | −151.8 (2) | C29—N3—C25—C26 | 106.1 (2) |
C6—C7—C8—C9 | 1.1 (3) | C29—C30—C31—C32 | 1.2 (3) |
C7—C6—C11—C10 | 2.5 (3) | C30—C29—C34—C33 | 0.5 (3) |
C7—C6—C11—C14 | −178.9 (2) | C30—C29—C34—C37 | 178.7 (2) |
C7—C8—C9—C10 | 0.5 (3) | C30—C31—C32—C33 | −0.3 (3) |
C7—C8—C9—C13 | −177.7 (2) | C30—C31—C32—C36 | 177.1 (2) |
C8—C9—C10—C11 | −0.7 (4) | C31—C32—C33—C34 | −0.5 (3) |
C9—C10—C11—C6 | −0.8 (4) | C32—C33—C34—C29 | 0.4 (3) |
C9—C10—C11—C14 | −179.4 (2) | C32—C33—C34—C37 | −177.8 (2) |
C11—C6—C7—C8 | −2.7 (3) | C34—C29—C30—C31 | −1.3 (3) |
C11—C6—C7—C12 | 178.2 (2) | C34—C29—C30—C35 | −179.8 (2) |
C12—C7—C8—C9 | −179.7 (2) | C35—C30—C31—C32 | 179.7 (2) |
C13—C9—C10—C11 | 177.6 (2) | C36—C32—C33—C34 | −177.8 (2) |
C15—N2—C1—Se1 | 12.3 (3) | C38—N4—C24—Se2 | 9.6 (3) |
C15—N2—C1—N1 | −168.57 (19) | C38—N4—C24—N3 | −169.51 (19) |
C15—N2—C5—C4 | 102.3 (2) | C38—N4—C28—C27 | −146.7 (2) |
C15—C16—C17—C18 | 0.3 (3) | C38—C39—C40—C41 | 1.1 (3) |
C16—C15—C20—C19 | −0.5 (3) | C39—C38—C43—C42 | −2.4 (3) |
C16—C15—C20—C23 | −177.7 (2) | C39—C38—C43—C46 | 178.9 (2) |
C16—C17—C18—C19 | −1.0 (3) | C39—C40—C41—C42 | −1.4 (3) |
C16—C17—C18—C22 | 176.9 (2) | C39—C40—C41—C45 | 179.7 (2) |
C17—C18—C19—C20 | 1.0 (3) | C40—C41—C42—C43 | −0.2 (3) |
C18—C19—C20—C15 | −0.2 (3) | C41—C42—C43—C38 | 2.1 (3) |
C18—C19—C20—C23 | 177.0 (2) | C41—C42—C43—C46 | −179.3 (2) |
C20—C15—C16—C17 | 0.4 (3) | C43—C38—C39—C40 | 0.9 (3) |
C20—C15—C16—C21 | 177.9 (2) | C43—C38—C39—C44 | 179.1 (2) |
C21—C16—C17—C18 | −177.2 (2) | C44—C39—C40—C41 | −177.1 (2) |
C22—C18—C19—C20 | −176.9 (2) | C45—C41—C42—C43 | 178.6 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2B···Se1i | 0.99 | 3.02 | 3.671 (2) | 125 |
C3—H3A···Se1i | 0.99 | 2.88 | 3.665 (2) | 137 |
C4—H4B···Se2ii | 0.99 | 3.12 | 3.641 (2) | 114 |
C5—H5A···Se2ii | 0.99 | 3.09 | 3.754 (2) | 126 |
C26—H26B···Se2iii | 0.99 | 2.94 | 3.796 (2) | 146 |
Symmetry codes: (i) −x+1/2, y+1/2, z; (ii) −x+1, −y+1, −z+1; (iii) −x+1/2, y−1/2, z. |
C23H30N2S·C2H3N | F(000) = 880 |
Mr = 407.60 | Dx = 1.200 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 13.0884 (6) Å | Cell parameters from 9891 reflections |
b = 12.9760 (5) Å | θ = 2.3–27.5° |
c = 14.4293 (7) Å | µ = 0.16 mm−1 |
β = 113.028 (2)° | T = 100 K |
V = 2255.32 (18) Å3 | Plank, colourless |
Z = 4 | 0.26 × 0.17 × 0.10 mm |
Bruker D8 Venture Photon 2 diffractometer | 4419 reflections with I > 2σ(I) |
Radiation source: Incoatec IµS | Rint = 0.046 |
φ and ω scans | θmax = 27.5°, θmin = 2.2° |
Absorption correction: multi-scan SADABS v2016/2 (Bruker AXS Inc., 2017) | h = −16→17 |
Tmin = 0.711, Tmax = 0.746 | k = −16→16 |
34671 measured reflections | l = −18→18 |
5148 independent reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.096 | H-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 parameters | Δρmax = 0.28 e Å−3 |
36 restraints | Δρmin = −0.21 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
S1 | 0.43804 (3) | 0.35053 (3) | 0.58591 (3) | 0.02002 (9) | |
N1 | 0.28488 (9) | 0.23910 (8) | 0.61966 (8) | 0.0165 (2) | |
N2 | 0.46730 (9) | 0.20752 (8) | 0.72720 (9) | 0.0187 (2) | |
N3 | 0.09785 (14) | 0.67080 (12) | 0.36918 (13) | 0.0476 (4) | |
C1 | 0.39454 (10) | 0.26151 (10) | 0.64704 (10) | 0.0166 (3) | |
C2 | 0.23875 (11) | 0.20489 (10) | 0.69367 (10) | 0.0197 (3) | |
H2A | 0.158630 | 0.221813 | 0.666660 | 0.024* | |
H2B | 0.275153 | 0.244855 | 0.756507 | 0.024* | |
C3 | 0.25226 (12) | 0.09117 (11) | 0.71954 (12) | 0.0244 (3) | 0.853 (4) |
H3A | 0.228597 | 0.050171 | 0.656754 | 0.029* | 0.853 (4) |
H3B | 0.204117 | 0.072263 | 0.755400 | 0.029* | 0.853 (4) |
C4 | 0.37427 (14) | 0.06553 (13) | 0.78649 (15) | 0.0222 (4) | 0.853 (4) |
H4A | 0.396298 | 0.103339 | 0.850990 | 0.027* | 0.853 (4) |
H4B | 0.381061 | −0.009156 | 0.801739 | 0.027* | 0.853 (4) |
C5 | 0.45187 (13) | 0.09440 (12) | 0.73532 (14) | 0.0184 (4) | 0.853 (4) |
H5A | 0.525312 | 0.062796 | 0.773239 | 0.022* | 0.853 (4) |
H5B | 0.422643 | 0.064450 | 0.666758 | 0.022* | 0.853 (4) |
C3B | 0.25226 (12) | 0.09117 (11) | 0.71954 (12) | 0.0244 (3) | 0.147 (4) |
H3BA | 0.246800 | 0.080709 | 0.785409 | 0.029* | 0.147 (4) |
H3BB | 0.190672 | 0.052680 | 0.668254 | 0.029* | 0.147 (4) |
C4B | 0.3582 (8) | 0.0489 (7) | 0.7244 (9) | 0.023 (2) | 0.147 (4) |
H4BA | 0.359614 | 0.046335 | 0.656333 | 0.027* | 0.147 (4) |
H4BB | 0.369209 | −0.021765 | 0.752537 | 0.027* | 0.147 (4) |
C5B | 0.4460 (8) | 0.1189 (8) | 0.7908 (8) | 0.020 (2) | 0.147 (4) |
H5BA | 0.515448 | 0.079555 | 0.825370 | 0.024* | 0.147 (4) |
H5BB | 0.422805 | 0.148530 | 0.842708 | 0.024* | 0.147 (4) |
C6 | 0.20570 (10) | 0.28179 (10) | 0.52689 (10) | 0.0163 (3) | |
C7 | 0.15783 (10) | 0.37797 (10) | 0.52853 (10) | 0.0184 (3) | |
C8 | 0.08166 (10) | 0.41758 (10) | 0.43835 (10) | 0.0192 (3) | |
H8 | 0.048292 | 0.482545 | 0.438570 | 0.023* | |
C9 | 0.05303 (10) | 0.36447 (10) | 0.34774 (10) | 0.0187 (3) | |
C10 | 0.10009 (11) | 0.26778 (10) | 0.34924 (10) | 0.0185 (3) | |
H10 | 0.079210 | 0.229709 | 0.288364 | 0.022* | |
C11 | 0.17719 (10) | 0.22557 (10) | 0.43810 (10) | 0.0173 (3) | |
C12 | 0.18995 (12) | 0.43966 (11) | 0.62429 (11) | 0.0246 (3) | |
H12A | 0.167502 | 0.511629 | 0.607762 | 0.037* | |
H12B | 0.270551 | 0.436191 | 0.661594 | 0.037* | |
H12C | 0.152680 | 0.411279 | 0.665779 | 0.037* | |
C13 | −0.02441 (11) | 0.41249 (11) | 0.24993 (11) | 0.0234 (3) | |
H13A | −0.093642 | 0.432848 | 0.255975 | 0.035* | |
H13B | −0.040698 | 0.362349 | 0.195213 | 0.035* | |
H13C | 0.010950 | 0.473390 | 0.235227 | 0.035* | |
C14 | 0.22854 (12) | 0.12205 (11) | 0.43677 (11) | 0.0229 (3) | |
H14A | 0.309381 | 0.129308 | 0.461515 | 0.034* | |
H14B | 0.199912 | 0.095343 | 0.367747 | 0.034* | |
H14C | 0.209742 | 0.074104 | 0.480178 | 0.034* | |
C15 | 0.57768 (11) | 0.24817 (10) | 0.78090 (10) | 0.0179 (3) | |
C16 | 0.59395 (11) | 0.31750 (10) | 0.85958 (10) | 0.0188 (3) | |
C17 | 0.70119 (11) | 0.35298 (10) | 0.91484 (10) | 0.0203 (3) | |
H17 | 0.713024 | 0.399966 | 0.968560 | 0.024* | |
C18 | 0.79137 (11) | 0.32167 (11) | 0.89370 (10) | 0.0210 (3) | |
C19 | 0.77190 (11) | 0.25361 (11) | 0.81392 (10) | 0.0207 (3) | |
H19 | 0.832619 | 0.232259 | 0.798086 | 0.025* | |
C20 | 0.66612 (11) | 0.21580 (10) | 0.75651 (10) | 0.0195 (3) | |
C21 | 0.49809 (11) | 0.35392 (11) | 0.88439 (11) | 0.0228 (3) | |
H21A | 0.523644 | 0.408264 | 0.935516 | 0.034* | |
H21B | 0.469045 | 0.296015 | 0.910328 | 0.034* | |
H21C | 0.439327 | 0.381115 | 0.823437 | 0.034* | |
C22 | 0.90777 (12) | 0.35963 (12) | 0.95412 (12) | 0.0281 (3) | |
H22A | 0.905297 | 0.414202 | 1.000146 | 0.042* | |
H22B | 0.940177 | 0.386907 | 0.908357 | 0.042* | |
H22C | 0.953302 | 0.302382 | 0.993033 | 0.042* | |
C23 | 0.64884 (12) | 0.14485 (11) | 0.66898 (11) | 0.0257 (3) | |
H23A | 0.708850 | 0.154847 | 0.645302 | 0.039* | |
H23B | 0.577439 | 0.160375 | 0.614221 | 0.039* | |
H23C | 0.648980 | 0.073193 | 0.690472 | 0.039* | |
C24 | 0.18720 (14) | 0.64241 (12) | 0.41048 (12) | 0.0315 (4) | |
C25 | 0.29974 (13) | 0.60517 (12) | 0.46426 (13) | 0.0313 (3) | |
H25A | 0.329179 | 0.632888 | 0.532906 | 0.047* | |
H25B | 0.346612 | 0.627785 | 0.429237 | 0.047* | |
H25C | 0.299335 | 0.529708 | 0.466905 | 0.047* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.01496 (16) | 0.02198 (17) | 0.02167 (17) | −0.00078 (12) | 0.00560 (13) | 0.00425 (13) |
N1 | 0.0129 (5) | 0.0196 (5) | 0.0156 (5) | 0.0005 (4) | 0.0040 (4) | 0.0018 (4) |
N2 | 0.0138 (5) | 0.0164 (5) | 0.0214 (6) | −0.0005 (4) | 0.0020 (4) | 0.0038 (4) |
N3 | 0.0424 (9) | 0.0371 (8) | 0.0448 (9) | −0.0020 (7) | −0.0029 (7) | 0.0127 (7) |
C1 | 0.0146 (6) | 0.0160 (6) | 0.0178 (6) | 0.0017 (5) | 0.0048 (5) | −0.0015 (5) |
C2 | 0.0175 (6) | 0.0239 (7) | 0.0188 (6) | 0.0016 (5) | 0.0082 (5) | 0.0017 (5) |
C3 | 0.0242 (7) | 0.0228 (7) | 0.0299 (8) | −0.0002 (6) | 0.0147 (6) | 0.0050 (6) |
C4 | 0.0241 (9) | 0.0197 (8) | 0.0240 (10) | 0.0017 (6) | 0.0109 (8) | 0.0051 (7) |
C5 | 0.0173 (7) | 0.0152 (7) | 0.0217 (9) | 0.0016 (6) | 0.0065 (6) | 0.0018 (6) |
C3B | 0.0242 (7) | 0.0228 (7) | 0.0299 (8) | −0.0002 (6) | 0.0147 (6) | 0.0050 (6) |
C4B | 0.022 (4) | 0.018 (4) | 0.023 (4) | −0.001 (3) | 0.004 (3) | 0.007 (3) |
C5B | 0.021 (4) | 0.022 (4) | 0.020 (4) | 0.008 (3) | 0.009 (3) | 0.009 (3) |
C6 | 0.0109 (5) | 0.0206 (6) | 0.0156 (6) | −0.0010 (5) | 0.0035 (5) | 0.0020 (5) |
C7 | 0.0134 (6) | 0.0222 (6) | 0.0192 (6) | −0.0006 (5) | 0.0058 (5) | −0.0004 (5) |
C8 | 0.0140 (6) | 0.0204 (6) | 0.0229 (7) | 0.0024 (5) | 0.0069 (5) | 0.0021 (5) |
C9 | 0.0125 (6) | 0.0248 (7) | 0.0186 (6) | −0.0009 (5) | 0.0057 (5) | 0.0041 (5) |
C10 | 0.0144 (6) | 0.0240 (6) | 0.0166 (6) | −0.0029 (5) | 0.0053 (5) | −0.0008 (5) |
C11 | 0.0135 (6) | 0.0189 (6) | 0.0193 (6) | −0.0018 (5) | 0.0062 (5) | 0.0003 (5) |
C12 | 0.0242 (7) | 0.0247 (7) | 0.0216 (7) | 0.0069 (6) | 0.0052 (6) | −0.0032 (6) |
C13 | 0.0184 (6) | 0.0288 (7) | 0.0203 (7) | 0.0027 (5) | 0.0044 (5) | 0.0053 (6) |
C14 | 0.0245 (7) | 0.0209 (7) | 0.0216 (7) | 0.0018 (5) | 0.0073 (6) | −0.0018 (5) |
C15 | 0.0136 (6) | 0.0190 (6) | 0.0176 (6) | −0.0006 (5) | 0.0022 (5) | 0.0035 (5) |
C16 | 0.0175 (6) | 0.0197 (6) | 0.0184 (6) | 0.0016 (5) | 0.0061 (5) | 0.0040 (5) |
C17 | 0.0201 (6) | 0.0217 (6) | 0.0179 (6) | −0.0008 (5) | 0.0062 (5) | −0.0017 (5) |
C18 | 0.0160 (6) | 0.0238 (7) | 0.0204 (7) | −0.0012 (5) | 0.0040 (5) | 0.0010 (5) |
C19 | 0.0148 (6) | 0.0246 (7) | 0.0216 (7) | 0.0023 (5) | 0.0058 (5) | 0.0001 (5) |
C20 | 0.0181 (6) | 0.0193 (6) | 0.0185 (6) | 0.0023 (5) | 0.0043 (5) | 0.0013 (5) |
C21 | 0.0190 (6) | 0.0281 (7) | 0.0225 (7) | 0.0026 (5) | 0.0095 (6) | 0.0013 (6) |
C22 | 0.0175 (7) | 0.0341 (8) | 0.0290 (8) | −0.0041 (6) | 0.0053 (6) | −0.0069 (6) |
C23 | 0.0208 (7) | 0.0280 (7) | 0.0245 (7) | 0.0029 (6) | 0.0046 (6) | −0.0061 (6) |
C24 | 0.0391 (9) | 0.0238 (7) | 0.0262 (8) | −0.0071 (6) | 0.0069 (7) | 0.0029 (6) |
C25 | 0.0302 (8) | 0.0290 (8) | 0.0348 (9) | −0.0028 (6) | 0.0128 (7) | −0.0034 (7) |
S1—C1 | 1.6821 (14) | C10—H10 | 0.9500 |
N1—C1 | 1.3627 (16) | C10—C11 | 1.3964 (18) |
N1—C2 | 1.4854 (17) | C11—C14 | 1.5055 (18) |
N1—C6 | 1.4448 (16) | C12—H12A | 0.9800 |
N2—C1 | 1.3688 (16) | C12—H12B | 0.9800 |
N2—C5 | 1.4925 (18) | C12—H12C | 0.9800 |
N2—C5B | 1.563 (9) | C13—H13A | 0.9800 |
N2—C15 | 1.4456 (16) | C13—H13B | 0.9800 |
N3—C24 | 1.146 (2) | C13—H13C | 0.9800 |
C2—H2A | 0.9900 | C14—H14A | 0.9800 |
C2—H2B | 0.9900 | C14—H14B | 0.9800 |
C2—C3 | 1.5154 (19) | C14—H14C | 0.9800 |
C2—C3B | 1.5154 (19) | C15—C16 | 1.3980 (19) |
C3—H3A | 0.9900 | C15—C20 | 1.3997 (19) |
C3—H3B | 0.9900 | C16—C17 | 1.3936 (19) |
C3—C4 | 1.545 (2) | C16—C21 | 1.5090 (19) |
C4—H4A | 0.9900 | C17—H17 | 0.9500 |
C4—H4B | 0.9900 | C17—C18 | 1.390 (2) |
C4—C5 | 1.518 (2) | C18—C19 | 1.393 (2) |
C5—H5A | 0.9900 | C18—C22 | 1.5114 (19) |
C5—H5B | 0.9900 | C19—H19 | 0.9500 |
C3B—H3BA | 0.9900 | C19—C20 | 1.3952 (19) |
C3B—H3BB | 0.9900 | C20—C23 | 1.5068 (19) |
C3B—C4B | 1.467 (10) | C21—H21A | 0.9800 |
C4B—H4BA | 0.9900 | C21—H21B | 0.9800 |
C4B—H4BB | 0.9900 | C21—H21C | 0.9800 |
C4B—C5B | 1.485 (15) | C22—H22A | 0.9800 |
C5B—H5BA | 0.9900 | C22—H22B | 0.9800 |
C5B—H5BB | 0.9900 | C22—H22C | 0.9800 |
C6—C7 | 1.4009 (18) | C23—H23A | 0.9800 |
C6—C11 | 1.3924 (18) | C23—H23B | 0.9800 |
C7—C8 | 1.3915 (18) | C23—H23C | 0.9800 |
C7—C12 | 1.5074 (19) | C24—C25 | 1.453 (2) |
C8—H8 | 0.9500 | C25—H25A | 0.9800 |
C8—C9 | 1.3934 (19) | C25—H25B | 0.9800 |
C9—C10 | 1.3940 (19) | C25—H25C | 0.9800 |
C9—C13 | 1.5128 (18) | ||
C1—N1—C2 | 122.24 (11) | C9—C10—C11 | 121.56 (12) |
C1—N1—C6 | 118.64 (11) | C11—C10—H10 | 119.2 |
C6—N1—C2 | 115.77 (10) | C6—C11—C10 | 118.46 (12) |
C1—N2—C5 | 119.93 (11) | C6—C11—C14 | 121.26 (12) |
C1—N2—C5B | 130.4 (4) | C10—C11—C14 | 120.27 (12) |
C1—N2—C15 | 119.03 (11) | C7—C12—H12A | 109.5 |
C15—N2—C5 | 117.02 (11) | C7—C12—H12B | 109.5 |
C15—N2—C5B | 108.9 (4) | C7—C12—H12C | 109.5 |
N1—C1—S1 | 121.91 (10) | H12A—C12—H12B | 109.5 |
N1—C1—N2 | 116.20 (11) | H12A—C12—H12C | 109.5 |
N2—C1—S1 | 121.89 (10) | H12B—C12—H12C | 109.5 |
N1—C2—H2A | 108.5 | C9—C13—H13A | 109.5 |
N1—C2—H2B | 108.5 | C9—C13—H13B | 109.5 |
N1—C2—C3 | 115.28 (11) | C9—C13—H13C | 109.5 |
N1—C2—C3B | 115.28 (11) | H13A—C13—H13B | 109.5 |
H2A—C2—H2B | 107.5 | H13A—C13—H13C | 109.5 |
C3—C2—H2A | 108.5 | H13B—C13—H13C | 109.5 |
C3—C2—H2B | 108.5 | C11—C14—H14A | 109.5 |
C2—C3—H3A | 109.5 | C11—C14—H14B | 109.5 |
C2—C3—H3B | 109.5 | C11—C14—H14C | 109.5 |
C2—C3—C4 | 110.87 (12) | H14A—C14—H14B | 109.5 |
H3A—C3—H3B | 108.1 | H14A—C14—H14C | 109.5 |
C4—C3—H3A | 109.5 | H14B—C14—H14C | 109.5 |
C4—C3—H3B | 109.5 | C16—C15—N2 | 118.23 (12) |
C3—C4—H4A | 109.3 | C16—C15—C20 | 121.26 (12) |
C3—C4—H4B | 109.3 | C20—C15—N2 | 120.47 (12) |
H4A—C4—H4B | 108.0 | C15—C16—C21 | 121.16 (12) |
C5—C4—C3 | 111.55 (14) | C17—C16—C15 | 118.47 (12) |
C5—C4—H4A | 109.3 | C17—C16—C21 | 120.37 (13) |
C5—C4—H4B | 109.3 | C16—C17—H17 | 119.0 |
N2—C5—C4 | 114.70 (14) | C18—C17—C16 | 121.96 (13) |
N2—C5—H5A | 108.6 | C18—C17—H17 | 119.0 |
N2—C5—H5B | 108.6 | C17—C18—C19 | 118.04 (12) |
C4—C5—H5A | 108.6 | C17—C18—C22 | 121.93 (13) |
C4—C5—H5B | 108.6 | C19—C18—C22 | 120.03 (13) |
H5A—C5—H5B | 107.6 | C18—C19—H19 | 118.9 |
C2—C3B—H3BA | 108.9 | C18—C19—C20 | 122.13 (13) |
C2—C3B—H3BB | 108.9 | C20—C19—H19 | 118.9 |
H3BA—C3B—H3BB | 107.8 | C15—C20—C23 | 121.76 (12) |
C4B—C3B—C2 | 113.2 (4) | C19—C20—C15 | 118.13 (13) |
C4B—C3B—H3BA | 108.9 | C19—C20—C23 | 120.08 (12) |
C4B—C3B—H3BB | 108.9 | C16—C21—H21A | 109.5 |
C3B—C4B—H4BA | 110.5 | C16—C21—H21B | 109.5 |
C3B—C4B—H4BB | 110.5 | C16—C21—H21C | 109.5 |
C3B—C4B—C5B | 106.3 (9) | H21A—C21—H21B | 109.5 |
H4BA—C4B—H4BB | 108.7 | H21A—C21—H21C | 109.5 |
C5B—C4B—H4BA | 110.5 | H21B—C21—H21C | 109.5 |
C5B—C4B—H4BB | 110.5 | C18—C22—H22A | 109.5 |
N2—C5B—H5BA | 109.7 | C18—C22—H22B | 109.5 |
N2—C5B—H5BB | 109.7 | C18—C22—H22C | 109.5 |
C4B—C5B—N2 | 110.0 (8) | H22A—C22—H22B | 109.5 |
C4B—C5B—H5BA | 109.7 | H22A—C22—H22C | 109.5 |
C4B—C5B—H5BB | 109.7 | H22B—C22—H22C | 109.5 |
H5BA—C5B—H5BB | 108.2 | C20—C23—H23A | 109.5 |
C7—C6—N1 | 119.30 (12) | C20—C23—H23B | 109.5 |
C11—C6—N1 | 119.25 (11) | C20—C23—H23C | 109.5 |
C11—C6—C7 | 121.45 (12) | H23A—C23—H23B | 109.5 |
C6—C7—C12 | 121.49 (12) | H23A—C23—H23C | 109.5 |
C8—C7—C6 | 118.34 (12) | H23B—C23—H23C | 109.5 |
C8—C7—C12 | 120.13 (12) | N3—C24—C25 | 178.80 (19) |
C7—C8—H8 | 119.1 | C24—C25—H25A | 109.5 |
C7—C8—C9 | 121.74 (12) | C24—C25—H25B | 109.5 |
C9—C8—H8 | 119.1 | C24—C25—H25C | 109.5 |
C8—C9—C10 | 118.40 (12) | H25A—C25—H25B | 109.5 |
C8—C9—C13 | 120.52 (12) | H25A—C25—H25C | 109.5 |
C10—C9—C13 | 121.06 (13) | H25B—C25—H25C | 109.5 |
C9—C10—H10 | 119.2 | ||
N1—C2—C3—C4 | 72.82 (16) | C5B—N2—C15—C20 | 98.3 (5) |
N1—C2—C3B—C4B | 37.0 (5) | C6—N1—C1—S1 | 9.29 (17) |
N1—C6—C7—C8 | −179.91 (11) | C6—N1—C1—N2 | −170.76 (11) |
N1—C6—C7—C12 | 2.12 (19) | C6—N1—C2—C3 | 118.47 (13) |
N1—C6—C11—C10 | 179.67 (11) | C6—N1—C2—C3B | 118.47 (13) |
N1—C6—C11—C14 | −0.92 (18) | C6—C7—C8—C9 | −0.4 (2) |
N2—C15—C16—C17 | 176.86 (12) | C7—C6—C11—C10 | 0.82 (19) |
N2—C15—C16—C21 | −3.40 (19) | C7—C6—C11—C14 | −179.77 (12) |
N2—C15—C20—C19 | −176.92 (12) | C7—C8—C9—C10 | 2.0 (2) |
N2—C15—C20—C23 | 5.0 (2) | C7—C8—C9—C13 | −176.07 (12) |
C1—N1—C2—C3 | −82.51 (16) | C8—C9—C10—C11 | −2.25 (19) |
C1—N1—C2—C3B | −82.51 (16) | C9—C10—C11—C6 | 0.87 (19) |
C1—N1—C6—C7 | −89.84 (15) | C9—C10—C11—C14 | −178.55 (12) |
C1—N1—C6—C11 | 91.29 (15) | C11—C6—C7—C8 | −1.07 (19) |
C1—N2—C5—C4 | −86.51 (18) | C11—C6—C7—C12 | −179.03 (12) |
C1—N2—C5B—C4B | 38.3 (10) | C12—C7—C8—C9 | 177.61 (12) |
C1—N2—C15—C16 | 87.17 (16) | C13—C9—C10—C11 | 175.81 (12) |
C1—N2—C15—C20 | −94.99 (15) | C15—N2—C1—S1 | 19.92 (17) |
C2—N1—C1—S1 | −149.15 (10) | C15—N2—C1—N1 | −160.03 (12) |
C2—N1—C1—N2 | 30.80 (17) | C15—N2—C5—C4 | 116.25 (15) |
C2—N1—C6—C7 | 69.98 (15) | C15—N2—C5B—C4B | −156.9 (6) |
C2—N1—C6—C11 | −108.90 (13) | C15—C16—C17—C18 | 0.2 (2) |
C2—C3—C4—C5 | −58.41 (18) | C16—C15—C20—C19 | 0.9 (2) |
C2—C3B—C4B—C5B | 50.5 (8) | C16—C15—C20—C23 | −177.21 (13) |
C3—C4—C5—N2 | 70.95 (19) | C16—C17—C18—C19 | 0.7 (2) |
C5—N2—C1—S1 | −136.86 (12) | C16—C17—C18—C22 | −179.58 (13) |
C5—N2—C1—N1 | 43.19 (18) | C17—C18—C19—C20 | −0.8 (2) |
C5—N2—C15—C16 | −115.39 (15) | C18—C19—C20—C15 | 0.0 (2) |
C5—N2—C15—C20 | 62.46 (18) | C18—C19—C20—C23 | 178.14 (13) |
C3B—C4B—C5B—N2 | −88.9 (9) | C20—C15—C16—C17 | −1.0 (2) |
C5B—N2—C1—S1 | −176.6 (6) | C20—C15—C16—C21 | 178.77 (12) |
C5B—N2—C1—N1 | 3.4 (6) | C21—C16—C17—C18 | −179.56 (13) |
C5B—N2—C15—C16 | −79.6 (5) | C22—C18—C19—C20 | 179.46 (13) |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4B···S1i | 0.99 | 2.92 | 3.6972 (17) | 136 |
C25—H25B···S1ii | 0.98 | 2.92 | 3.8180 (17) | 152 |
Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) −x+1, −y+1, −z+1. |
C23H30N2Se·C2H3N | F(000) = 952 |
Mr = 454.50 | Dx = 1.319 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 13.1365 (3) Å | Cell parameters from 9757 reflections |
b = 13.3024 (2) Å | θ = 2.2–27.5° |
c = 14.2478 (3) Å | µ = 1.66 mm−1 |
β = 113.1557 (7)° | T = 100 K |
V = 2289.18 (8) Å3 | Block, yellow |
Z = 4 | 0.23 × 0.19 × 0.10 mm |
Bruker D8 Venture Photon 2 diffractometer | 4637 reflections with I > 2σ(I) |
Radiation source: Incoatec IµS | Rint = 0.046 |
φ and ω scans | θmax = 27.5°, θmin = 2.2° |
Absorption correction: multi-scan SADABS v2016/2 (Bruker AXS Inc., 2017) | h = −17→17 |
Tmin = 0.683, Tmax = 0.746 | k = −17→17 |
40871 measured reflections | l = −18→18 |
5251 independent reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.026 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.061 | H-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 parameters | Δρmax = 0.36 e Å−3 |
36 restraints | Δρmin = −0.33 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Se1 | 0.44339 (2) | 0.35467 (2) | 0.58253 (2) | 0.01973 (5) | |
N1 | 0.28687 (10) | 0.24512 (10) | 0.62785 (9) | 0.0161 (3) | |
N2 | 0.46935 (11) | 0.21612 (10) | 0.73881 (11) | 0.0213 (3) | |
C1 | 0.39611 (13) | 0.26432 (11) | 0.65558 (12) | 0.0172 (3) | |
C2 | 0.24099 (13) | 0.20892 (12) | 0.70159 (12) | 0.0188 (3) | |
H2A | 0.162063 | 0.228586 | 0.676798 | 0.023* | |
H2B | 0.280551 | 0.242782 | 0.767936 | 0.023* | |
C3 | 0.24979 (14) | 0.09602 (13) | 0.71822 (14) | 0.0249 (4) | 0.367 (5) |
H3A | 0.229112 | 0.060344 | 0.652320 | 0.030* | 0.367 (5) |
H3B | 0.200194 | 0.073442 | 0.751383 | 0.030* | 0.367 (5) |
C3B | 0.24979 (14) | 0.09602 (13) | 0.71822 (14) | 0.0249 (4) | 0.633 (5) |
H3BA | 0.238342 | 0.079486 | 0.781118 | 0.030* | 0.633 (5) |
H3BB | 0.190978 | 0.062271 | 0.660168 | 0.030* | 0.633 (5) |
C4 | 0.3775 (4) | 0.0740 (3) | 0.7910 (4) | 0.0212 (11) | 0.367 (5) |
H4A | 0.397775 | 0.113169 | 0.854907 | 0.025* | 0.367 (5) |
H4B | 0.386508 | 0.001783 | 0.809187 | 0.025* | 0.367 (5) |
C4B | 0.3613 (2) | 0.0575 (2) | 0.7277 (2) | 0.0204 (7) | 0.633 (5) |
H4BA | 0.363737 | 0.054038 | 0.659173 | 0.024* | 0.633 (5) |
H4BB | 0.372806 | −0.011230 | 0.756732 | 0.024* | 0.633 (5) |
C5 | 0.4536 (4) | 0.1018 (3) | 0.7391 (4) | 0.0185 (11) | 0.367 (5) |
H5A | 0.422354 | 0.076777 | 0.667898 | 0.022* | 0.367 (5) |
H5B | 0.526456 | 0.069135 | 0.774958 | 0.022* | 0.367 (5) |
C5B | 0.4524 (2) | 0.1260 (2) | 0.7958 (2) | 0.0193 (7) | 0.633 (5) |
H5BA | 0.433628 | 0.149539 | 0.852944 | 0.023* | 0.633 (5) |
H5BB | 0.522381 | 0.087522 | 0.825080 | 0.023* | 0.633 (5) |
C6 | 0.20736 (12) | 0.28483 (12) | 0.53284 (11) | 0.0160 (3) | |
C7 | 0.15910 (12) | 0.37867 (12) | 0.53314 (12) | 0.0175 (3) | |
C8 | 0.08250 (12) | 0.41582 (12) | 0.44127 (12) | 0.0187 (3) | |
H8 | 0.049180 | 0.479378 | 0.440462 | 0.022* | |
C9 | 0.05335 (12) | 0.36221 (12) | 0.35034 (12) | 0.0184 (3) | |
C10 | 0.10020 (12) | 0.26774 (12) | 0.35358 (12) | 0.0181 (3) | |
H10 | 0.078740 | 0.229323 | 0.292621 | 0.022* | |
C11 | 0.17782 (12) | 0.22801 (12) | 0.44398 (12) | 0.0172 (3) | |
C12 | 0.19143 (14) | 0.44013 (13) | 0.62932 (12) | 0.0237 (3) | |
H12A | 0.169388 | 0.510262 | 0.611603 | 0.036* | |
H12B | 0.271797 | 0.436567 | 0.667311 | 0.036* | |
H12C | 0.154138 | 0.413551 | 0.671618 | 0.036* | |
C13 | −0.02406 (13) | 0.40737 (14) | 0.25048 (12) | 0.0234 (3) | |
H13A | −0.088689 | 0.435953 | 0.258942 | 0.035* | |
H13B | −0.048286 | 0.354999 | 0.197891 | 0.035* | |
H13C | 0.014561 | 0.460457 | 0.229806 | 0.035* | |
C14 | 0.22918 (14) | 0.12664 (12) | 0.44389 (13) | 0.0227 (3) | |
H14A | 0.309892 | 0.133508 | 0.470215 | 0.034* | |
H14B | 0.201674 | 0.100365 | 0.374036 | 0.034* | |
H14C | 0.209353 | 0.080169 | 0.487356 | 0.034* | |
C15 | 0.58038 (12) | 0.25532 (12) | 0.78975 (12) | 0.0189 (3) | |
C16 | 0.59968 (13) | 0.32537 (12) | 0.86766 (12) | 0.0202 (3) | |
C17 | 0.70831 (14) | 0.35784 (13) | 0.92191 (12) | 0.0221 (3) | |
H17 | 0.722717 | 0.404635 | 0.975998 | 0.027* | |
C18 | 0.79588 (13) | 0.32364 (13) | 0.89901 (13) | 0.0222 (3) | |
C19 | 0.77327 (13) | 0.25401 (13) | 0.82044 (12) | 0.0216 (3) | |
H19 | 0.832340 | 0.230125 | 0.803889 | 0.026* | |
C20 | 0.66649 (13) | 0.21832 (12) | 0.76533 (12) | 0.0211 (3) | |
C21 | 0.50612 (14) | 0.36652 (14) | 0.89236 (13) | 0.0256 (4) | |
H21A | 0.534310 | 0.419661 | 0.943789 | 0.038* | |
H21B | 0.474426 | 0.312396 | 0.919020 | 0.038* | |
H21C | 0.448837 | 0.394234 | 0.830324 | 0.038* | |
C22 | 0.91285 (14) | 0.36019 (15) | 0.95683 (14) | 0.0300 (4) | |
H22A | 0.912669 | 0.414434 | 1.003306 | 0.045* | |
H22B | 0.943119 | 0.385324 | 0.908463 | 0.045* | |
H22C | 0.958675 | 0.304515 | 0.996261 | 0.045* | |
C23 | 0.64518 (15) | 0.14426 (14) | 0.67956 (14) | 0.0312 (4) | |
H23A | 0.710600 | 0.140119 | 0.662776 | 0.047* | |
H23B | 0.581416 | 0.166603 | 0.619380 | 0.047* | |
H23C | 0.629677 | 0.077905 | 0.700787 | 0.047* | |
N3 | 0.07928 (16) | 0.66649 (14) | 0.36865 (15) | 0.0471 (5) | |
C24 | 0.17011 (17) | 0.64243 (14) | 0.40537 (14) | 0.0313 (4) | |
C25 | 0.28509 (16) | 0.61080 (15) | 0.45398 (16) | 0.0335 (4) | |
H25A | 0.320731 | 0.645878 | 0.519306 | 0.050* | |
H25B | 0.323767 | 0.627122 | 0.409489 | 0.050* | |
H25C | 0.288256 | 0.538100 | 0.465909 | 0.050* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Se1 | 0.01439 (8) | 0.02322 (9) | 0.02095 (8) | −0.00069 (6) | 0.00629 (6) | 0.00366 (6) |
N1 | 0.0141 (6) | 0.0181 (6) | 0.0157 (6) | 0.0007 (5) | 0.0055 (5) | 0.0013 (5) |
N2 | 0.0135 (6) | 0.0189 (7) | 0.0270 (7) | −0.0004 (5) | 0.0031 (5) | 0.0073 (6) |
C1 | 0.0158 (7) | 0.0155 (7) | 0.0190 (7) | 0.0007 (6) | 0.0054 (6) | −0.0023 (6) |
C2 | 0.0172 (7) | 0.0222 (8) | 0.0184 (7) | 0.0017 (6) | 0.0087 (6) | 0.0013 (6) |
C3 | 0.0246 (8) | 0.0247 (9) | 0.0299 (9) | 0.0001 (7) | 0.0154 (7) | 0.0061 (7) |
C3B | 0.0246 (8) | 0.0247 (9) | 0.0299 (9) | 0.0001 (7) | 0.0154 (7) | 0.0061 (7) |
C4 | 0.021 (2) | 0.020 (2) | 0.024 (3) | 0.0033 (17) | 0.0091 (18) | 0.0034 (18) |
C4B | 0.0218 (13) | 0.0167 (12) | 0.0204 (15) | −0.0024 (10) | 0.0059 (11) | −0.0001 (10) |
C5 | 0.018 (2) | 0.015 (2) | 0.020 (2) | −0.0002 (16) | 0.0058 (17) | −0.0003 (17) |
C5B | 0.0209 (12) | 0.0165 (13) | 0.0176 (14) | 0.0005 (10) | 0.0046 (10) | 0.0041 (10) |
C6 | 0.0113 (7) | 0.0198 (7) | 0.0162 (7) | −0.0001 (6) | 0.0049 (6) | 0.0022 (6) |
C7 | 0.0135 (7) | 0.0196 (8) | 0.0194 (7) | −0.0008 (6) | 0.0064 (6) | −0.0007 (6) |
C8 | 0.0140 (7) | 0.0208 (8) | 0.0219 (8) | 0.0022 (6) | 0.0075 (6) | 0.0020 (6) |
C9 | 0.0129 (7) | 0.0247 (8) | 0.0178 (7) | −0.0008 (6) | 0.0063 (6) | 0.0026 (6) |
C10 | 0.0154 (7) | 0.0231 (8) | 0.0161 (7) | −0.0039 (6) | 0.0064 (6) | −0.0014 (6) |
C11 | 0.0140 (7) | 0.0192 (7) | 0.0195 (7) | −0.0014 (6) | 0.0080 (6) | 0.0001 (6) |
C12 | 0.0212 (8) | 0.0241 (8) | 0.0220 (8) | 0.0059 (7) | 0.0043 (7) | −0.0035 (7) |
C13 | 0.0179 (8) | 0.0305 (9) | 0.0199 (8) | 0.0021 (7) | 0.0055 (6) | 0.0034 (7) |
C14 | 0.0249 (8) | 0.0220 (8) | 0.0202 (8) | 0.0031 (7) | 0.0077 (7) | −0.0001 (6) |
C15 | 0.0136 (7) | 0.0204 (8) | 0.0195 (7) | 0.0000 (6) | 0.0032 (6) | 0.0059 (6) |
C16 | 0.0188 (8) | 0.0229 (8) | 0.0198 (7) | 0.0024 (6) | 0.0086 (6) | 0.0059 (6) |
C17 | 0.0223 (8) | 0.0249 (8) | 0.0185 (7) | −0.0004 (7) | 0.0073 (6) | −0.0024 (6) |
C18 | 0.0172 (8) | 0.0253 (8) | 0.0218 (8) | −0.0018 (6) | 0.0053 (6) | 0.0005 (7) |
C19 | 0.0152 (7) | 0.0262 (9) | 0.0220 (8) | 0.0025 (6) | 0.0059 (6) | −0.0006 (7) |
C20 | 0.0189 (8) | 0.0196 (8) | 0.0205 (8) | 0.0022 (6) | 0.0031 (6) | 0.0001 (6) |
C21 | 0.0210 (8) | 0.0323 (10) | 0.0248 (8) | 0.0053 (7) | 0.0104 (7) | 0.0034 (7) |
C22 | 0.0189 (8) | 0.0383 (10) | 0.0304 (9) | −0.0067 (7) | 0.0071 (7) | −0.0074 (8) |
C23 | 0.0230 (9) | 0.0303 (10) | 0.0308 (9) | 0.0054 (7) | 0.0005 (7) | −0.0105 (8) |
N3 | 0.0389 (10) | 0.0387 (10) | 0.0461 (11) | −0.0018 (8) | −0.0021 (9) | 0.0150 (8) |
C24 | 0.0371 (11) | 0.0256 (9) | 0.0256 (9) | −0.0068 (8) | 0.0063 (8) | 0.0043 (7) |
C25 | 0.0295 (10) | 0.0319 (10) | 0.0390 (11) | −0.0058 (8) | 0.0132 (8) | −0.0060 (8) |
Se1—C1 | 1.8498 (16) | C10—C11 | 1.395 (2) |
N1—C1 | 1.355 (2) | C11—C14 | 1.508 (2) |
N1—C2 | 1.482 (2) | C12—H12A | 0.9800 |
N1—C6 | 1.4458 (19) | C12—H12B | 0.9800 |
N2—C1 | 1.359 (2) | C12—H12C | 0.9800 |
N2—C5 | 1.535 (5) | C13—H13A | 0.9800 |
N2—C5B | 1.512 (3) | C13—H13B | 0.9800 |
N2—C15 | 1.4469 (19) | C13—H13C | 0.9800 |
C2—H2A | 0.9900 | C14—H14A | 0.9800 |
C2—H2B | 0.9900 | C14—H14B | 0.9800 |
C2—C3 | 1.518 (2) | C14—H14C | 0.9800 |
C2—C3B | 1.518 (2) | C15—C16 | 1.394 (2) |
C3—H3A | 0.9900 | C15—C20 | 1.397 (2) |
C3—H3B | 0.9900 | C16—C17 | 1.397 (2) |
C3—C4 | 1.614 (5) | C16—C21 | 1.508 (2) |
C3B—H3BA | 0.9900 | C17—H17 | 0.9500 |
C3B—H3BB | 0.9900 | C17—C18 | 1.390 (2) |
C3B—C4B | 1.507 (3) | C18—C19 | 1.392 (2) |
C4—H4A | 0.9900 | C18—C22 | 1.510 (2) |
C4—H4B | 0.9900 | C19—H19 | 0.9500 |
C4—C5 | 1.506 (7) | C19—C20 | 1.394 (2) |
C4B—H4BA | 0.9900 | C20—C23 | 1.508 (2) |
C4B—H4BB | 0.9900 | C21—H21A | 0.9800 |
C4B—C5B | 1.514 (4) | C21—H21B | 0.9800 |
C5—H5A | 0.9900 | C21—H21C | 0.9800 |
C5—H5B | 0.9900 | C22—H22A | 0.9800 |
C5B—H5BA | 0.9900 | C22—H22B | 0.9800 |
C5B—H5BB | 0.9900 | C22—H22C | 0.9800 |
C6—C7 | 1.401 (2) | C23—H23A | 0.9800 |
C6—C11 | 1.392 (2) | C23—H23B | 0.9800 |
C7—C8 | 1.391 (2) | C23—H23C | 0.9800 |
C7—C12 | 1.506 (2) | N3—C24 | 1.144 (3) |
C8—H8 | 0.9500 | C24—C25 | 1.455 (3) |
C8—C9 | 1.394 (2) | C25—H25A | 0.9800 |
C9—C10 | 1.392 (2) | C25—H25B | 0.9800 |
C9—C13 | 1.510 (2) | C25—H25C | 0.9800 |
C10—H10 | 0.9500 | ||
C1—N1—C2 | 122.27 (13) | C9—C10—C11 | 121.73 (15) |
C1—N1—C6 | 119.78 (13) | C11—C10—H10 | 119.1 |
C6—N1—C2 | 115.91 (12) | C6—C11—C10 | 118.38 (14) |
C1—N2—C5 | 114.8 (2) | C6—C11—C14 | 121.42 (14) |
C1—N2—C5B | 129.74 (15) | C10—C11—C14 | 120.19 (14) |
C1—N2—C15 | 119.73 (13) | C7—C12—H12A | 109.5 |
C15—N2—C5 | 117.8 (2) | C7—C12—H12B | 109.5 |
C15—N2—C5B | 110.40 (14) | C7—C12—H12C | 109.5 |
N1—C1—Se1 | 120.66 (11) | H12A—C12—H12B | 109.5 |
N1—C1—N2 | 118.10 (14) | H12A—C12—H12C | 109.5 |
N2—C1—Se1 | 121.23 (12) | H12B—C12—H12C | 109.5 |
N1—C2—H2A | 108.8 | C9—C13—H13A | 109.5 |
N1—C2—H2B | 108.8 | C9—C13—H13B | 109.5 |
N1—C2—C3 | 113.88 (13) | C9—C13—H13C | 109.5 |
N1—C2—C3B | 113.88 (13) | H13A—C13—H13B | 109.5 |
H2A—C2—H2B | 107.7 | H13A—C13—H13C | 109.5 |
C3—C2—H2A | 108.8 | H13B—C13—H13C | 109.5 |
C3—C2—H2B | 108.8 | C11—C14—H14A | 109.5 |
C2—C3—H3A | 110.5 | C11—C14—H14B | 109.5 |
C2—C3—H3B | 110.5 | C11—C14—H14C | 109.5 |
C2—C3—C4 | 106.0 (2) | H14A—C14—H14B | 109.5 |
H3A—C3—H3B | 108.7 | H14A—C14—H14C | 109.5 |
C4—C3—H3A | 110.5 | H14B—C14—H14C | 109.5 |
C4—C3—H3B | 110.5 | C16—C15—N2 | 118.18 (15) |
C2—C3B—H3BA | 109.4 | C16—C15—C20 | 121.48 (14) |
C2—C3B—H3BB | 109.4 | C20—C15—N2 | 120.21 (15) |
H3BA—C3B—H3BB | 108.0 | C15—C16—C17 | 118.26 (15) |
C4B—C3B—C2 | 111.26 (16) | C15—C16—C21 | 121.24 (15) |
C4B—C3B—H3BA | 109.4 | C17—C16—C21 | 120.50 (15) |
C4B—C3B—H3BB | 109.4 | C16—C17—H17 | 119.1 |
C3—C4—H4A | 109.4 | C18—C17—C16 | 121.90 (16) |
C3—C4—H4B | 109.4 | C18—C17—H17 | 119.1 |
H4A—C4—H4B | 108.0 | C17—C18—C19 | 118.17 (15) |
C5—C4—C3 | 111.3 (4) | C17—C18—C22 | 121.67 (16) |
C5—C4—H4A | 109.4 | C19—C18—C22 | 120.16 (16) |
C5—C4—H4B | 109.4 | C18—C19—H19 | 119.0 |
C3B—C4B—H4BA | 109.6 | C18—C19—C20 | 121.92 (16) |
C3B—C4B—H4BB | 109.6 | C20—C19—H19 | 119.0 |
C3B—C4B—C5B | 110.3 (2) | C15—C20—C23 | 121.44 (15) |
H4BA—C4B—H4BB | 108.1 | C19—C20—C15 | 118.26 (15) |
C5B—C4B—H4BA | 109.6 | C19—C20—C23 | 120.27 (15) |
C5B—C4B—H4BB | 109.6 | C16—C21—H21A | 109.5 |
N2—C5—H5A | 109.4 | C16—C21—H21B | 109.5 |
N2—C5—H5B | 109.4 | C16—C21—H21C | 109.5 |
C4—C5—N2 | 111.1 (4) | H21A—C21—H21B | 109.5 |
C4—C5—H5A | 109.4 | H21A—C21—H21C | 109.5 |
C4—C5—H5B | 109.4 | H21B—C21—H21C | 109.5 |
H5A—C5—H5B | 108.0 | C18—C22—H22A | 109.5 |
N2—C5B—C4B | 112.3 (2) | C18—C22—H22B | 109.5 |
N2—C5B—H5BA | 109.1 | C18—C22—H22C | 109.5 |
N2—C5B—H5BB | 109.1 | H22A—C22—H22B | 109.5 |
C4B—C5B—H5BA | 109.1 | H22A—C22—H22C | 109.5 |
C4B—C5B—H5BB | 109.1 | H22B—C22—H22C | 109.5 |
H5BA—C5B—H5BB | 107.9 | C20—C23—H23A | 109.5 |
C7—C6—N1 | 118.94 (14) | C20—C23—H23B | 109.5 |
C11—C6—N1 | 119.57 (14) | C20—C23—H23C | 109.5 |
C11—C6—C7 | 121.46 (14) | H23A—C23—H23B | 109.5 |
C6—C7—C12 | 121.36 (14) | H23A—C23—H23C | 109.5 |
C8—C7—C6 | 118.34 (14) | H23B—C23—H23C | 109.5 |
C8—C7—C12 | 120.27 (14) | N3—C24—C25 | 178.7 (2) |
C7—C8—H8 | 119.2 | C24—C25—H25A | 109.5 |
C7—C8—C9 | 121.70 (15) | C24—C25—H25B | 109.5 |
C9—C8—H8 | 119.2 | C24—C25—H25C | 109.5 |
C8—C9—C13 | 120.60 (15) | H25A—C25—H25B | 109.5 |
C10—C9—C8 | 118.34 (14) | H25A—C25—H25C | 109.5 |
C10—C9—C13 | 121.03 (15) | H25B—C25—H25C | 109.5 |
C9—C10—H10 | 119.1 | ||
N1—C2—C3—C4 | 76.4 (2) | C5B—N2—C15—C20 | 88.8 (2) |
N1—C2—C3B—C4B | 42.9 (2) | C6—N1—C1—Se1 | 8.35 (19) |
N1—C6—C7—C8 | −179.80 (14) | C6—N1—C1—N2 | −172.24 (14) |
N1—C6—C7—C12 | 2.2 (2) | C6—N1—C2—C3 | 112.40 (15) |
N1—C6—C11—C10 | 179.43 (14) | C6—N1—C2—C3B | 112.40 (15) |
N1—C6—C11—C14 | −1.6 (2) | C6—C7—C8—C9 | 0.0 (2) |
N2—C15—C16—C17 | 175.44 (14) | C7—C6—C11—C10 | 1.5 (2) |
N2—C15—C16—C21 | −5.4 (2) | C7—C6—C11—C14 | −179.52 (15) |
N2—C15—C20—C19 | −176.33 (14) | C7—C8—C9—C10 | 2.1 (2) |
N2—C15—C20—C23 | 5.6 (2) | C7—C8—C9—C13 | −175.77 (15) |
C1—N1—C2—C3 | −83.91 (18) | C8—C9—C10—C11 | −2.5 (2) |
C1—N1—C2—C3B | −83.91 (18) | C9—C10—C11—C6 | 0.7 (2) |
C1—N1—C6—C7 | −91.48 (18) | C9—C10—C11—C14 | −178.26 (15) |
C1—N1—C6—C11 | 90.54 (18) | C11—C6—C7—C8 | −1.9 (2) |
C1—N2—C5—C4 | −90.9 (4) | C11—C6—C7—C12 | −179.83 (15) |
C1—N2—C5B—C4B | 28.1 (4) | C12—C7—C8—C9 | 177.99 (15) |
C1—N2—C15—C16 | 89.25 (19) | C13—C9—C10—C11 | 175.38 (14) |
C1—N2—C15—C20 | −94.90 (19) | C15—N2—C1—Se1 | 18.5 (2) |
C2—N1—C1—Se1 | −154.72 (12) | C15—N2—C1—N1 | −160.95 (14) |
C2—N1—C1—N2 | 24.7 (2) | C15—N2—C5—C4 | 119.6 (3) |
C2—N1—C6—C7 | 72.64 (18) | C15—N2—C5B—C4B | −156.2 (2) |
C2—N1—C6—C11 | −105.35 (16) | C15—C16—C17—C18 | 1.1 (2) |
C2—C3—C4—C5 | −63.8 (4) | C16—C15—C20—C19 | −0.6 (2) |
C2—C3B—C4B—C5B | 43.9 (3) | C16—C15—C20—C23 | −178.66 (16) |
C3—C4—C5—N2 | 76.3 (5) | C16—C17—C18—C19 | −0.9 (3) |
C3B—C4B—C5B—N2 | −82.9 (3) | C16—C17—C18—C22 | 179.05 (16) |
C5—N2—C1—Se1 | −130.4 (2) | C17—C18—C19—C20 | −0.1 (3) |
C5—N2—C1—N1 | 50.2 (3) | C18—C19—C20—C15 | 0.9 (3) |
C5—N2—C15—C16 | −122.8 (3) | C18—C19—C20—C23 | 178.94 (16) |
C5—N2—C15—C20 | 53.0 (3) | C20—C15—C16—C17 | −0.4 (2) |
C5B—N2—C1—Se1 | −166.11 (19) | C20—C15—C16—C21 | 178.83 (15) |
C5B—N2—C1—N1 | 14.5 (3) | C21—C16—C17—C18 | −178.05 (16) |
C5B—N2—C15—C16 | −87.0 (2) | C22—C18—C19—C20 | 179.91 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4A···Se1i | 0.99 | 3.09 | 4.009 (6) | 155 |
C4—H4B···Se1ii | 0.99 | 2.91 | 3.737 (4) | 141 |
C4B—H4BB···Se1ii | 0.99 | 3.15 | 3.965 (3) | 141 |
C25—H25B···Se1iii | 0.98 | 3.03 | 3.829 (2) | 140 |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+1, y−1/2, −z+3/2; (iii) −x+1, −y+1, −z+1. |
C23H30I2N2S | Z = 2 |
Mr = 620.35 | F(000) = 608 |
Triclinic, P1 | Dx = 1.694 Mg m−3 |
a = 7.9505 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.5048 (4) Å | Cell parameters from 9861 reflections |
c = 18.2812 (9) Å | θ = 2.3–27.3° |
α = 81.040 (3)° | µ = 2.68 mm−1 |
β = 89.926 (2)° | T = 100 K |
γ = 85.125 (2)° | Plate, red |
V = 1216.54 (10) Å3 | 0.17 × 0.12 × 0.08 mm |
Bruker D8 Venture Photon 2 diffractometer | 4834 reflections with I > 2σ(I) |
Radiation source: Incoatec IµS | Rint = 0.067 |
φ and ω scans | θmax = 27.4°, θmin = 2.4° |
Absorption correction: multi-scan SADABS v2016/2 (Bruker AXS Inc., 2017) | h = −10→10 |
Tmin = 0.636, Tmax = 0.746 | k = −10→10 |
37544 measured reflections | l = −23→23 |
5455 independent reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.072 | H-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 parameters | Δρmax = 1.35 e Å−3 |
0 restraints | Δρmin = −1.40 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
I1 | 0.28705 (3) | 0.88440 (3) | 0.22530 (2) | 0.01492 (7) | |
I2 | 0.06264 (3) | 1.09545 (3) | 0.12352 (2) | 0.02728 (8) | |
S1 | 0.47932 (10) | 0.66975 (11) | 0.31875 (5) | 0.01703 (18) | |
N1 | 0.8088 (3) | 0.6376 (3) | 0.33943 (15) | 0.0127 (6) | |
N2 | 0.7225 (3) | 0.6387 (3) | 0.21680 (15) | 0.0130 (6) | |
C1 | 0.6852 (4) | 0.6480 (4) | 0.28741 (19) | 0.0134 (7) | |
C2 | 0.9843 (4) | 0.5614 (4) | 0.3374 (2) | 0.0168 (7) | |
H2A | 1.018107 | 0.509455 | 0.388167 | 0.020* | |
H2B | 1.061092 | 0.645979 | 0.322132 | 0.020* | |
C3 | 1.0080 (5) | 0.4375 (5) | 0.2856 (2) | 0.0213 (8) | |
H3A | 1.114530 | 0.370121 | 0.298913 | 0.026* | |
H3B | 0.914180 | 0.367398 | 0.292614 | 0.026* | |
C4 | 1.0133 (4) | 0.5118 (5) | 0.2043 (2) | 0.0196 (8) | |
H4A | 1.129903 | 0.537851 | 0.191607 | 0.024* | |
H4B | 0.981390 | 0.433713 | 0.173079 | 0.024* | |
C5 | 0.8946 (4) | 0.6622 (4) | 0.18810 (19) | 0.0158 (7) | |
H5A | 0.941171 | 0.747917 | 0.210723 | 0.019* | |
H5B | 0.887569 | 0.697375 | 0.133882 | 0.019* | |
C6 | 0.7742 (4) | 0.7057 (4) | 0.40671 (18) | 0.0139 (7) | |
C7 | 0.7426 (4) | 0.6058 (4) | 0.47232 (19) | 0.0159 (7) | |
C8 | 0.7116 (4) | 0.6771 (5) | 0.53581 (19) | 0.0179 (7) | |
H8 | 0.686611 | 0.611912 | 0.580889 | 0.021* | |
C9 | 0.7166 (5) | 0.8403 (5) | 0.5346 (2) | 0.0207 (8) | |
C10 | 0.7539 (5) | 0.9335 (5) | 0.4683 (2) | 0.0208 (8) | |
H10 | 0.760278 | 1.044830 | 0.467324 | 0.025* | |
C11 | 0.7822 (4) | 0.8702 (4) | 0.4034 (2) | 0.0168 (7) | |
C12 | 0.7344 (5) | 0.4291 (4) | 0.4761 (2) | 0.0220 (8) | |
H12A | 0.687198 | 0.407252 | 0.429589 | 0.033* | |
H12B | 0.662310 | 0.389509 | 0.517285 | 0.033* | |
H12C | 0.848221 | 0.375011 | 0.483966 | 0.033* | |
C13 | 0.6858 (6) | 0.9149 (5) | 0.6037 (2) | 0.0301 (9) | |
H13A | 0.793836 | 0.936811 | 0.623955 | 0.045* | |
H13B | 0.629485 | 0.841323 | 0.640475 | 0.045* | |
H13C | 0.613919 | 1.015073 | 0.591360 | 0.045* | |
C14 | 0.8136 (5) | 0.9761 (5) | 0.3316 (2) | 0.0244 (8) | |
H14A | 0.920452 | 0.938395 | 0.310805 | 0.037* | |
H14B | 0.819568 | 1.086062 | 0.340714 | 0.037* | |
H14C | 0.721199 | 0.972794 | 0.296618 | 0.037* | |
C15 | 0.5972 (4) | 0.6111 (4) | 0.16372 (18) | 0.0128 (7) | |
C16 | 0.5322 (4) | 0.4619 (4) | 0.16910 (19) | 0.0144 (7) | |
C17 | 0.4114 (4) | 0.4417 (4) | 0.11705 (19) | 0.0150 (7) | |
H17 | 0.365081 | 0.341456 | 0.120577 | 0.018* | |
C18 | 0.3563 (4) | 0.5630 (5) | 0.0602 (2) | 0.0185 (7) | |
C19 | 0.4284 (4) | 0.7073 (4) | 0.05493 (19) | 0.0173 (7) | |
H19 | 0.394263 | 0.790240 | 0.015399 | 0.021* | |
C20 | 0.5490 (4) | 0.7349 (4) | 0.10561 (19) | 0.0154 (7) | |
C21 | 0.5925 (5) | 0.3234 (4) | 0.2275 (2) | 0.0197 (7) | |
H21A | 0.522420 | 0.234631 | 0.225713 | 0.030* | |
H21B | 0.584081 | 0.356488 | 0.276435 | 0.030* | |
H21C | 0.710358 | 0.288864 | 0.218221 | 0.030* | |
C22 | 0.2198 (4) | 0.5396 (5) | 0.0072 (2) | 0.0219 (8) | |
H22A | 0.194199 | 0.427520 | 0.015651 | 0.033* | |
H22B | 0.258125 | 0.567836 | −0.043793 | 0.033* | |
H22C | 0.118065 | 0.608065 | 0.015052 | 0.033* | |
C23 | 0.6172 (5) | 0.8963 (4) | 0.0964 (2) | 0.0204 (8) | |
H23A | 0.665570 | 0.912993 | 0.143618 | 0.031* | |
H23B | 0.525513 | 0.979378 | 0.081082 | 0.031* | |
H23C | 0.704890 | 0.901765 | 0.058623 | 0.031* |
U11 | U22 | U33 | U12 | U13 | U23 | |
I1 | 0.01112 (11) | 0.01644 (12) | 0.01866 (12) | −0.00050 (8) | 0.00204 (8) | −0.00765 (9) |
I2 | 0.02175 (13) | 0.01754 (13) | 0.03991 (17) | 0.00034 (10) | −0.00680 (11) | 0.00272 (11) |
S1 | 0.0101 (4) | 0.0260 (5) | 0.0145 (4) | 0.0008 (3) | 0.0011 (3) | −0.0028 (4) |
N1 | 0.0117 (13) | 0.0123 (14) | 0.0134 (14) | 0.0019 (11) | 0.0013 (10) | −0.0015 (11) |
N2 | 0.0102 (13) | 0.0167 (15) | 0.0129 (14) | −0.0022 (11) | 0.0026 (10) | −0.0039 (11) |
C1 | 0.0127 (15) | 0.0128 (16) | 0.0150 (16) | 0.0002 (12) | 0.0018 (12) | −0.0035 (13) |
C2 | 0.0105 (15) | 0.0200 (18) | 0.0193 (18) | 0.0027 (13) | −0.0015 (13) | −0.0035 (14) |
C3 | 0.0172 (17) | 0.0200 (19) | 0.026 (2) | 0.0055 (14) | −0.0001 (14) | −0.0046 (16) |
C4 | 0.0116 (16) | 0.023 (2) | 0.0254 (19) | 0.0040 (14) | 0.0029 (14) | −0.0103 (16) |
C5 | 0.0084 (15) | 0.0220 (19) | 0.0171 (17) | −0.0031 (13) | 0.0049 (12) | −0.0023 (14) |
C6 | 0.0106 (15) | 0.0165 (18) | 0.0143 (16) | 0.0030 (13) | −0.0024 (12) | −0.0039 (14) |
C7 | 0.0125 (15) | 0.0174 (18) | 0.0172 (17) | 0.0005 (13) | −0.0023 (13) | −0.0022 (14) |
C8 | 0.0162 (16) | 0.0224 (19) | 0.0130 (16) | 0.0017 (14) | 0.0005 (13) | 0.0016 (14) |
C9 | 0.0208 (18) | 0.024 (2) | 0.0184 (18) | 0.0040 (15) | −0.0034 (14) | −0.0098 (15) |
C10 | 0.0250 (18) | 0.0154 (18) | 0.0232 (19) | 0.0015 (14) | −0.0003 (15) | −0.0084 (15) |
C11 | 0.0143 (16) | 0.0163 (18) | 0.0198 (18) | 0.0015 (13) | 0.0004 (13) | −0.0043 (14) |
C12 | 0.0261 (19) | 0.0162 (19) | 0.024 (2) | −0.0016 (15) | 0.0023 (15) | −0.0035 (15) |
C13 | 0.037 (2) | 0.035 (2) | 0.019 (2) | 0.0080 (19) | −0.0023 (17) | −0.0148 (18) |
C14 | 0.033 (2) | 0.017 (2) | 0.023 (2) | −0.0012 (16) | 0.0029 (16) | −0.0035 (16) |
C15 | 0.0097 (14) | 0.0182 (17) | 0.0110 (15) | −0.0011 (13) | 0.0020 (12) | −0.0042 (13) |
C16 | 0.0145 (16) | 0.0129 (17) | 0.0157 (16) | 0.0011 (13) | 0.0042 (13) | −0.0031 (13) |
C17 | 0.0099 (15) | 0.0188 (18) | 0.0188 (17) | −0.0010 (13) | 0.0052 (13) | −0.0105 (14) |
C18 | 0.0108 (15) | 0.030 (2) | 0.0164 (17) | 0.0016 (14) | 0.0037 (13) | −0.0099 (15) |
C19 | 0.0177 (16) | 0.0196 (18) | 0.0129 (16) | 0.0047 (14) | 0.0007 (13) | −0.0006 (14) |
C20 | 0.0161 (16) | 0.0148 (17) | 0.0152 (17) | −0.0001 (13) | 0.0037 (13) | −0.0028 (14) |
C21 | 0.0192 (17) | 0.0149 (18) | 0.0244 (19) | −0.0013 (14) | −0.0011 (14) | −0.0011 (15) |
C22 | 0.0167 (17) | 0.030 (2) | 0.0205 (19) | −0.0012 (15) | −0.0009 (14) | −0.0074 (16) |
C23 | 0.0212 (18) | 0.0188 (19) | 0.0205 (19) | −0.0003 (14) | 0.0026 (14) | −0.0015 (15) |
I1—I2 | 2.8794 (4) | C11—C14 | 1.505 (5) |
I1—S1 | 2.6738 (9) | C12—H12A | 0.9800 |
S1—C1 | 1.738 (3) | C12—H12B | 0.9800 |
N1—C1 | 1.356 (4) | C12—H12C | 0.9800 |
N1—C2 | 1.491 (4) | C13—H13A | 0.9800 |
N1—C6 | 1.455 (4) | C13—H13B | 0.9800 |
N2—C1 | 1.337 (4) | C13—H13C | 0.9800 |
N2—C5 | 1.483 (4) | C14—H14A | 0.9800 |
N2—C15 | 1.449 (4) | C14—H14B | 0.9800 |
C2—H2A | 0.9900 | C14—H14C | 0.9800 |
C2—H2B | 0.9900 | C15—C16 | 1.400 (5) |
C2—C3 | 1.524 (5) | C15—C20 | 1.402 (5) |
C3—H3A | 0.9900 | C16—C17 | 1.393 (5) |
C3—H3B | 0.9900 | C16—C21 | 1.507 (5) |
C3—C4 | 1.523 (5) | C17—H17 | 0.9500 |
C4—H4A | 0.9900 | C17—C18 | 1.388 (5) |
C4—H4B | 0.9900 | C18—C19 | 1.389 (5) |
C4—C5 | 1.514 (5) | C18—C22 | 1.502 (5) |
C5—H5A | 0.9900 | C19—H19 | 0.9500 |
C5—H5B | 0.9900 | C19—C20 | 1.393 (5) |
C6—C7 | 1.393 (5) | C20—C23 | 1.504 (5) |
C6—C11 | 1.398 (5) | C21—H21A | 0.9800 |
C7—C8 | 1.403 (5) | C21—H21B | 0.9800 |
C7—C12 | 1.501 (5) | C21—H21C | 0.9800 |
C8—H8 | 0.9500 | C22—H22A | 0.9800 |
C8—C9 | 1.388 (5) | C22—H22B | 0.9800 |
C9—C10 | 1.388 (5) | C22—H22C | 0.9800 |
C9—C13 | 1.509 (5) | C23—H23A | 0.9800 |
C10—H10 | 0.9500 | C23—H23B | 0.9800 |
C10—C11 | 1.388 (5) | C23—H23C | 0.9800 |
S1—I1—I2 | 175.38 (2) | C7—C12—H12B | 109.5 |
C1—S1—I1 | 111.45 (12) | C7—C12—H12C | 109.5 |
C1—N1—C2 | 127.7 (3) | H12A—C12—H12B | 109.5 |
C1—N1—C6 | 119.4 (3) | H12A—C12—H12C | 109.5 |
C6—N1—C2 | 112.9 (3) | H12B—C12—H12C | 109.5 |
C1—N2—C5 | 121.2 (3) | C9—C13—H13A | 109.5 |
C1—N2—C15 | 122.3 (3) | C9—C13—H13B | 109.5 |
C15—N2—C5 | 116.4 (3) | C9—C13—H13C | 109.5 |
N1—C1—S1 | 116.0 (2) | H13A—C13—H13B | 109.5 |
N2—C1—S1 | 123.0 (2) | H13A—C13—H13C | 109.5 |
N2—C1—N1 | 121.0 (3) | H13B—C13—H13C | 109.5 |
N1—C2—H2A | 108.6 | C11—C14—H14A | 109.5 |
N1—C2—H2B | 108.6 | C11—C14—H14B | 109.5 |
N1—C2—C3 | 114.6 (3) | C11—C14—H14C | 109.5 |
H2A—C2—H2B | 107.6 | H14A—C14—H14B | 109.5 |
C3—C2—H2A | 108.6 | H14A—C14—H14C | 109.5 |
C3—C2—H2B | 108.6 | H14B—C14—H14C | 109.5 |
C2—C3—H3A | 109.0 | C16—C15—N2 | 120.3 (3) |
C2—C3—H3B | 109.0 | C16—C15—C20 | 121.3 (3) |
H3A—C3—H3B | 107.8 | C20—C15—N2 | 118.4 (3) |
C4—C3—C2 | 113.0 (3) | C15—C16—C21 | 122.2 (3) |
C4—C3—H3A | 109.0 | C17—C16—C15 | 118.1 (3) |
C4—C3—H3B | 109.0 | C17—C16—C21 | 119.7 (3) |
C3—C4—H4A | 109.4 | C16—C17—H17 | 118.9 |
C3—C4—H4B | 109.4 | C18—C17—C16 | 122.3 (3) |
H4A—C4—H4B | 108.0 | C18—C17—H17 | 118.9 |
C5—C4—C3 | 111.4 (3) | C17—C18—C19 | 118.0 (3) |
C5—C4—H4A | 109.4 | C17—C18—C22 | 120.8 (3) |
C5—C4—H4B | 109.4 | C19—C18—C22 | 121.2 (3) |
N2—C5—C4 | 112.6 (3) | C18—C19—H19 | 118.8 |
N2—C5—H5A | 109.1 | C18—C19—C20 | 122.3 (3) |
N2—C5—H5B | 109.1 | C20—C19—H19 | 118.8 |
C4—C5—H5A | 109.1 | C15—C20—C23 | 123.5 (3) |
C4—C5—H5B | 109.1 | C19—C20—C15 | 117.9 (3) |
H5A—C5—H5B | 107.8 | C19—C20—C23 | 118.5 (3) |
C7—C6—N1 | 119.7 (3) | C16—C21—H21A | 109.5 |
C7—C6—C11 | 122.3 (3) | C16—C21—H21B | 109.5 |
C11—C6—N1 | 117.9 (3) | C16—C21—H21C | 109.5 |
C6—C7—C8 | 117.5 (3) | H21A—C21—H21B | 109.5 |
C6—C7—C12 | 122.5 (3) | H21A—C21—H21C | 109.5 |
C8—C7—C12 | 120.0 (3) | H21B—C21—H21C | 109.5 |
C7—C8—H8 | 119.1 | C18—C22—H22A | 109.5 |
C9—C8—C7 | 121.9 (3) | C18—C22—H22B | 109.5 |
C9—C8—H8 | 119.1 | C18—C22—H22C | 109.5 |
C8—C9—C10 | 118.2 (3) | H22A—C22—H22B | 109.5 |
C8—C9—C13 | 121.3 (4) | H22A—C22—H22C | 109.5 |
C10—C9—C13 | 120.5 (4) | H22B—C22—H22C | 109.5 |
C9—C10—H10 | 118.7 | C20—C23—H23A | 109.5 |
C11—C10—C9 | 122.5 (3) | C20—C23—H23B | 109.5 |
C11—C10—H10 | 118.7 | C20—C23—H23C | 109.5 |
C6—C11—C14 | 121.4 (3) | H23A—C23—H23B | 109.5 |
C10—C11—C6 | 117.5 (3) | H23A—C23—H23C | 109.5 |
C10—C11—C14 | 121.1 (3) | H23B—C23—H23C | 109.5 |
C7—C12—H12A | 109.5 | ||
I1—S1—C1—N1 | 137.9 (2) | C6—N1—C2—C3 | 158.0 (3) |
I1—S1—C1—N2 | −43.2 (3) | C6—C7—C8—C9 | −1.8 (5) |
N1—C2—C3—C4 | 76.3 (4) | C7—C6—C11—C10 | −1.3 (5) |
N1—C6—C7—C8 | 179.3 (3) | C7—C6—C11—C14 | −178.9 (3) |
N1—C6—C7—C12 | −3.0 (5) | C7—C8—C9—C10 | −0.2 (5) |
N1—C6—C11—C10 | −178.2 (3) | C7—C8—C9—C13 | −179.0 (3) |
N1—C6—C11—C14 | 4.2 (5) | C8—C9—C10—C11 | 1.5 (5) |
N2—C15—C16—C17 | 179.6 (3) | C9—C10—C11—C6 | −0.8 (5) |
N2—C15—C16—C21 | −2.2 (5) | C9—C10—C11—C14 | 176.8 (4) |
N2—C15—C20—C19 | −179.9 (3) | C11—C6—C7—C8 | 2.6 (5) |
N2—C15—C20—C23 | −1.6 (5) | C11—C6—C7—C12 | −179.8 (3) |
C1—N1—C2—C3 | −21.6 (5) | C12—C7—C8—C9 | −179.5 (3) |
C1—N1—C6—C7 | 102.1 (4) | C13—C9—C10—C11 | −179.6 (3) |
C1—N1—C6—C11 | −81.0 (4) | C15—N2—C1—S1 | −13.8 (5) |
C1—N2—C5—C4 | 83.1 (4) | C15—N2—C1—N1 | 165.0 (3) |
C1—N2—C15—C16 | −70.4 (4) | C15—N2—C5—C4 | −99.0 (3) |
C1—N2—C15—C20 | 112.3 (4) | C15—C16—C17—C18 | 0.9 (5) |
C2—N1—C1—S1 | 155.4 (3) | C16—C15—C20—C19 | 2.8 (5) |
C2—N1—C1—N2 | −23.4 (5) | C16—C15—C20—C23 | −178.9 (3) |
C2—N1—C6—C7 | −77.6 (4) | C16—C17—C18—C19 | 1.5 (5) |
C2—N1—C6—C11 | 99.3 (3) | C16—C17—C18—C22 | −177.1 (3) |
C2—C3—C4—C5 | −35.7 (4) | C17—C18—C19—C20 | −1.8 (5) |
C3—C4—C5—N2 | −49.8 (4) | C18—C19—C20—C15 | −0.2 (5) |
C5—N2—C1—S1 | 164.0 (3) | C18—C19—C20—C23 | −178.6 (3) |
C5—N2—C1—N1 | −17.2 (5) | C20—C15—C16—C17 | −3.1 (5) |
C5—N2—C15—C16 | 111.8 (3) | C20—C15—C16—C21 | 175.0 (3) |
C5—N2—C15—C20 | −65.6 (4) | C21—C16—C17—C18 | −177.2 (3) |
C6—N1—C1—S1 | −24.2 (4) | C22—C18—C19—C20 | 176.7 (3) |
C6—N1—C1—N2 | 157.0 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2B···I1i | 0.99 | 3.16 | 4.111 (4) | 162 |
C4—H4B···I2ii | 0.99 | 3.16 | 4.034 (4) | 148 |
C5—H5A···I1i | 0.99 | 3.10 | 3.896 (3) | 138 |
Symmetry codes: (i) x+1, y, z; (ii) x+1, y−1, z. |
C23H30I2N2Se | Z = 2 |
Mr = 667.25 | F(000) = 644 |
Triclinic, P1 | Dx = 1.809 Mg m−3 |
a = 8.0282 (6) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.4305 (8) Å | Cell parameters from 9806 reflections |
c = 18.3525 (16) Å | θ = 2.5–30.6° |
α = 81.814 (4)° | µ = 4.06 mm−1 |
β = 89.706 (4)° | T = 100 K |
γ = 85.171 (4)° | Block, red |
V = 1225.08 (18) Å3 | 0.19 × 0.15 × 0.13 mm |
Bruker D8 Venture Photon 2 diffractometer | 6504 reflections with I > 2σ(I) |
Radiation source: Incoatec IµS | Rint = 0.045 |
φ and ω scans | θmax = 30.6°, θmin = 2.2° |
Absorption correction: multi-scan SADABS v2016/2 (Bruker AXS Inc., 2017) | h = −11→11 |
Tmin = 0.634, Tmax = 0.746 | k = −12→12 |
53696 measured reflections | l = −26→26 |
7479 independent reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.023 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.049 | H-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 parameters | Δρmax = 0.70 e Å−3 |
0 restraints | Δρmin = −0.75 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
I1 | 0.27703 (2) | 0.89168 (2) | 0.22239 (2) | 0.01494 (3) | |
I2 | 0.05678 (2) | 1.09633 (2) | 0.11610 (2) | 0.02769 (4) | |
Se1 | 0.46782 (2) | 0.67455 (3) | 0.32117 (2) | 0.01656 (5) | |
N1 | 0.7225 (2) | 0.6396 (2) | 0.21435 (9) | 0.0130 (3) | |
N2 | 0.8114 (2) | 0.6379 (2) | 0.33598 (9) | 0.0135 (3) | |
C1 | 0.6888 (2) | 0.6496 (2) | 0.28490 (10) | 0.0126 (3) | |
C2 | 0.8921 (2) | 0.6648 (3) | 0.18439 (11) | 0.0171 (4) | |
H2A | 0.938919 | 0.750832 | 0.207388 | 0.020* | |
H2B | 0.883119 | 0.701163 | 0.130732 | 0.020* | |
C3 | 1.0104 (3) | 0.5134 (3) | 0.19820 (12) | 0.0213 (4) | |
H3A | 1.125188 | 0.539814 | 0.184149 | 0.026* | |
H3B | 0.976698 | 0.434485 | 0.167193 | 0.026* | |
C4 | 1.0091 (3) | 0.4392 (3) | 0.27921 (12) | 0.0213 (4) | |
H4A | 0.917598 | 0.367027 | 0.286961 | 0.026* | |
H4B | 1.115861 | 0.373158 | 0.291258 | 0.026* | |
C5 | 0.9859 (2) | 0.5642 (3) | 0.33123 (11) | 0.0174 (4) | |
H5A | 1.023010 | 0.513272 | 0.381095 | 0.021* | |
H5B | 1.059496 | 0.650951 | 0.315169 | 0.021* | |
C6 | 0.5966 (2) | 0.6117 (2) | 0.16227 (10) | 0.0124 (3) | |
C7 | 0.5467 (2) | 0.7364 (2) | 0.10569 (11) | 0.0153 (4) | |
C8 | 0.4260 (2) | 0.7074 (3) | 0.05574 (11) | 0.0166 (4) | |
H8 | 0.390580 | 0.790458 | 0.017058 | 0.020* | |
C9 | 0.3562 (2) | 0.5609 (3) | 0.06083 (11) | 0.0161 (4) | |
C10 | 0.4131 (2) | 0.4383 (3) | 0.11640 (11) | 0.0152 (4) | |
H10 | 0.368015 | 0.336960 | 0.119653 | 0.018* | |
C11 | 0.5342 (2) | 0.4601 (2) | 0.16731 (11) | 0.0142 (4) | |
C12 | 0.6139 (3) | 0.8991 (3) | 0.09724 (12) | 0.0195 (4) | |
H12A | 0.659427 | 0.917317 | 0.144502 | 0.029* | |
H12B | 0.523485 | 0.982209 | 0.081462 | 0.029* | |
H12C | 0.702474 | 0.903782 | 0.060256 | 0.029* | |
C13 | 0.2204 (3) | 0.5367 (3) | 0.00849 (12) | 0.0211 (4) | |
H13A | 0.260793 | 0.557117 | −0.042190 | 0.032* | |
H13B | 0.122623 | 0.611284 | 0.014537 | 0.032* | |
H13C | 0.189295 | 0.425822 | 0.018970 | 0.032* | |
C14 | 0.5958 (3) | 0.3205 (3) | 0.22395 (12) | 0.0195 (4) | |
H14A | 0.523549 | 0.232564 | 0.223496 | 0.029* | |
H14B | 0.593290 | 0.354708 | 0.272823 | 0.029* | |
H14C | 0.710585 | 0.283492 | 0.212389 | 0.029* | |
C15 | 0.7790 (2) | 0.7038 (2) | 0.40398 (10) | 0.0143 (4) | |
C16 | 0.7841 (3) | 0.8691 (3) | 0.40316 (12) | 0.0177 (4) | |
C17 | 0.7552 (3) | 0.9309 (3) | 0.46878 (12) | 0.0219 (4) | |
H17 | 0.758966 | 1.043068 | 0.469232 | 0.026* | |
C18 | 0.7208 (3) | 0.8329 (3) | 0.53399 (12) | 0.0214 (4) | |
C19 | 0.7181 (3) | 0.6689 (3) | 0.53267 (11) | 0.0191 (4) | |
H19 | 0.694640 | 0.601188 | 0.576813 | 0.023* | |
C20 | 0.7489 (2) | 0.6004 (3) | 0.46836 (11) | 0.0162 (4) | |
C21 | 0.8131 (3) | 0.9791 (3) | 0.33286 (13) | 0.0246 (5) | |
H21A | 0.915278 | 0.939446 | 0.309426 | 0.037* | |
H21B | 0.825083 | 1.087843 | 0.344006 | 0.037* | |
H21C | 0.717856 | 0.981446 | 0.299430 | 0.037* | |
C22 | 0.6869 (4) | 0.9050 (3) | 0.60399 (13) | 0.0334 (6) | |
H22A | 0.626906 | 0.830949 | 0.638611 | 0.050* | |
H22B | 0.618810 | 1.007566 | 0.592576 | 0.050* | |
H22C | 0.793168 | 0.923296 | 0.626177 | 0.050* | |
C23 | 0.7446 (3) | 0.4213 (3) | 0.46971 (12) | 0.0215 (4) | |
H23A | 0.699897 | 0.399999 | 0.422795 | 0.032* | |
H23B | 0.673019 | 0.378779 | 0.509995 | 0.032* | |
H23C | 0.858093 | 0.368904 | 0.477201 | 0.032* |
U11 | U22 | U33 | U12 | U13 | U23 | |
I1 | 0.01234 (6) | 0.01620 (6) | 0.01713 (6) | −0.00217 (4) | 0.00048 (4) | −0.00470 (5) |
I2 | 0.02417 (8) | 0.01847 (7) | 0.03804 (9) | −0.00253 (5) | −0.01007 (6) | 0.00498 (6) |
Se1 | 0.01164 (9) | 0.02445 (11) | 0.01261 (9) | 0.00002 (7) | 0.00115 (7) | −0.00026 (8) |
N1 | 0.0114 (7) | 0.0165 (8) | 0.0117 (7) | −0.0045 (6) | 0.0011 (6) | −0.0020 (6) |
N2 | 0.0130 (7) | 0.0155 (8) | 0.0116 (7) | −0.0012 (6) | −0.0012 (6) | −0.0008 (6) |
C1 | 0.0122 (8) | 0.0121 (9) | 0.0130 (9) | −0.0012 (7) | −0.0004 (7) | 0.0000 (7) |
C2 | 0.0134 (9) | 0.0242 (11) | 0.0145 (9) | −0.0060 (8) | 0.0032 (7) | −0.0032 (8) |
C3 | 0.0166 (9) | 0.0268 (12) | 0.0225 (11) | −0.0011 (8) | 0.0042 (8) | −0.0107 (9) |
C4 | 0.0170 (9) | 0.0206 (11) | 0.0260 (11) | 0.0038 (8) | −0.0004 (8) | −0.0049 (9) |
C5 | 0.0133 (9) | 0.0213 (10) | 0.0169 (9) | 0.0009 (7) | −0.0011 (7) | −0.0017 (8) |
C6 | 0.0112 (8) | 0.0161 (9) | 0.0103 (8) | −0.0019 (7) | −0.0004 (6) | −0.0022 (7) |
C7 | 0.0150 (9) | 0.0173 (10) | 0.0134 (9) | −0.0024 (7) | 0.0020 (7) | −0.0013 (7) |
C8 | 0.0149 (9) | 0.0217 (10) | 0.0121 (9) | 0.0000 (7) | −0.0012 (7) | 0.0002 (7) |
C9 | 0.0118 (8) | 0.0235 (10) | 0.0137 (9) | −0.0010 (7) | −0.0002 (7) | −0.0049 (8) |
C10 | 0.0123 (8) | 0.0176 (10) | 0.0160 (9) | −0.0029 (7) | 0.0002 (7) | −0.0026 (7) |
C11 | 0.0125 (8) | 0.0175 (10) | 0.0126 (9) | −0.0014 (7) | 0.0005 (7) | −0.0015 (7) |
C12 | 0.0222 (10) | 0.0168 (10) | 0.0186 (10) | −0.0044 (8) | 0.0001 (8) | 0.0021 (8) |
C13 | 0.0150 (9) | 0.0325 (12) | 0.0167 (10) | −0.0051 (8) | −0.0030 (7) | −0.0047 (9) |
C14 | 0.0192 (10) | 0.0179 (10) | 0.0206 (10) | −0.0033 (8) | −0.0040 (8) | 0.0018 (8) |
C15 | 0.0134 (8) | 0.0181 (10) | 0.0113 (8) | −0.0001 (7) | −0.0016 (7) | −0.0020 (7) |
C16 | 0.0180 (9) | 0.0168 (10) | 0.0177 (10) | −0.0005 (7) | −0.0029 (7) | −0.0005 (8) |
C17 | 0.0285 (11) | 0.0161 (10) | 0.0218 (11) | 0.0003 (8) | −0.0027 (9) | −0.0058 (8) |
C18 | 0.0211 (10) | 0.0270 (12) | 0.0160 (10) | 0.0050 (8) | −0.0039 (8) | −0.0065 (8) |
C19 | 0.0192 (9) | 0.0256 (11) | 0.0109 (9) | 0.0007 (8) | −0.0022 (7) | 0.0008 (8) |
C20 | 0.0147 (9) | 0.0196 (10) | 0.0139 (9) | −0.0014 (7) | −0.0024 (7) | −0.0013 (7) |
C21 | 0.0358 (13) | 0.0156 (10) | 0.0216 (11) | −0.0037 (9) | 0.0030 (9) | 0.0010 (8) |
C22 | 0.0445 (15) | 0.0367 (15) | 0.0196 (11) | 0.0087 (12) | −0.0030 (10) | −0.0130 (10) |
C23 | 0.0263 (11) | 0.0192 (11) | 0.0183 (10) | −0.0052 (8) | −0.0025 (8) | 0.0017 (8) |
I1—I2 | 2.9107 (3) | C11—C14 | 1.506 (3) |
I1—Se1 | 2.7558 (3) | C12—H12A | 0.9800 |
Se1—C1 | 1.8974 (19) | C12—H12B | 0.9800 |
N1—C1 | 1.334 (2) | C12—H12C | 0.9800 |
N1—C2 | 1.487 (2) | C13—H13A | 0.9800 |
N1—C6 | 1.450 (2) | C13—H13B | 0.9800 |
N2—C1 | 1.351 (2) | C13—H13C | 0.9800 |
N2—C5 | 1.491 (3) | C14—H14A | 0.9800 |
N2—C15 | 1.450 (2) | C14—H14B | 0.9800 |
C2—H2A | 0.9900 | C14—H14C | 0.9800 |
C2—H2B | 0.9900 | C15—C16 | 1.396 (3) |
C2—C3 | 1.517 (3) | C15—C20 | 1.398 (3) |
C3—H3A | 0.9900 | C16—C17 | 1.390 (3) |
C3—H3B | 0.9900 | C16—C21 | 1.507 (3) |
C3—C4 | 1.529 (3) | C17—H17 | 0.9500 |
C4—H4A | 0.9900 | C17—C18 | 1.394 (3) |
C4—H4B | 0.9900 | C18—C19 | 1.388 (3) |
C4—C5 | 1.519 (3) | C18—C22 | 1.512 (3) |
C5—H5A | 0.9900 | C19—H19 | 0.9500 |
C5—H5B | 0.9900 | C19—C20 | 1.398 (3) |
C6—C7 | 1.402 (3) | C20—C23 | 1.509 (3) |
C6—C11 | 1.403 (3) | C21—H21A | 0.9800 |
C7—C8 | 1.397 (3) | C21—H21B | 0.9800 |
C7—C12 | 1.503 (3) | C21—H21C | 0.9800 |
C8—H8 | 0.9500 | C22—H22A | 0.9800 |
C8—C9 | 1.390 (3) | C22—H22B | 0.9800 |
C9—C10 | 1.393 (3) | C22—H22C | 0.9800 |
C9—C13 | 1.502 (3) | C23—H23A | 0.9800 |
C10—H10 | 0.9500 | C23—H23B | 0.9800 |
C10—C11 | 1.392 (3) | C23—H23C | 0.9800 |
Se1—I1—I2 | 174.620 (7) | C7—C12—H12B | 109.5 |
C1—Se1—I1 | 109.28 (6) | C7—C12—H12C | 109.5 |
C1—N1—C2 | 120.77 (16) | H12A—C12—H12B | 109.5 |
C1—N1—C6 | 122.74 (16) | H12A—C12—H12C | 109.5 |
C6—N1—C2 | 116.43 (15) | H12B—C12—H12C | 109.5 |
C1—N2—C5 | 127.28 (17) | C9—C13—H13A | 109.5 |
C1—N2—C15 | 119.63 (16) | C9—C13—H13B | 109.5 |
C15—N2—C5 | 113.08 (15) | C9—C13—H13C | 109.5 |
N1—C1—Se1 | 122.92 (14) | H13A—C13—H13B | 109.5 |
N1—C1—N2 | 121.70 (17) | H13A—C13—H13C | 109.5 |
N2—C1—Se1 | 115.36 (14) | H13B—C13—H13C | 109.5 |
N1—C2—H2A | 109.1 | C11—C14—H14A | 109.5 |
N1—C2—H2B | 109.1 | C11—C14—H14B | 109.5 |
N1—C2—C3 | 112.44 (17) | C11—C14—H14C | 109.5 |
H2A—C2—H2B | 107.8 | H14A—C14—H14B | 109.5 |
C3—C2—H2A | 109.1 | H14A—C14—H14C | 109.5 |
C3—C2—H2B | 109.1 | H14B—C14—H14C | 109.5 |
C2—C3—H3A | 109.4 | C16—C15—N2 | 118.39 (18) |
C2—C3—H3B | 109.4 | C16—C15—C20 | 122.13 (18) |
C2—C3—C4 | 110.98 (17) | C20—C15—N2 | 119.45 (18) |
H3A—C3—H3B | 108.0 | C15—C16—C21 | 121.32 (19) |
C4—C3—H3A | 109.4 | C17—C16—C15 | 118.01 (19) |
C4—C3—H3B | 109.4 | C17—C16—C21 | 120.6 (2) |
C3—C4—H4A | 109.0 | C16—C17—H17 | 119.1 |
C3—C4—H4B | 109.0 | C16—C17—C18 | 121.9 (2) |
H4A—C4—H4B | 107.8 | C18—C17—H17 | 119.1 |
C5—C4—C3 | 112.99 (18) | C17—C18—C22 | 120.3 (2) |
C5—C4—H4A | 109.0 | C19—C18—C17 | 118.4 (2) |
C5—C4—H4B | 109.0 | C19—C18—C22 | 121.3 (2) |
N2—C5—C4 | 114.95 (17) | C18—C19—H19 | 119.0 |
N2—C5—H5A | 108.5 | C18—C19—C20 | 122.0 (2) |
N2—C5—H5B | 108.5 | C20—C19—H19 | 119.0 |
C4—C5—H5A | 108.5 | C15—C20—C19 | 117.57 (19) |
C4—C5—H5B | 108.5 | C15—C20—C23 | 122.36 (18) |
H5A—C5—H5B | 107.5 | C19—C20—C23 | 120.05 (19) |
C7—C6—N1 | 118.43 (17) | C16—C21—H21A | 109.5 |
C7—C6—C11 | 121.73 (17) | C16—C21—H21B | 109.5 |
C11—C6—N1 | 119.76 (17) | C16—C21—H21C | 109.5 |
C6—C7—C12 | 123.38 (18) | H21A—C21—H21B | 109.5 |
C8—C7—C6 | 117.75 (18) | H21A—C21—H21C | 109.5 |
C8—C7—C12 | 118.87 (19) | H21B—C21—H21C | 109.5 |
C7—C8—H8 | 118.9 | C18—C22—H22A | 109.5 |
C9—C8—C7 | 122.10 (19) | C18—C22—H22B | 109.5 |
C9—C8—H8 | 118.9 | C18—C22—H22C | 109.5 |
C8—C9—C10 | 118.37 (18) | H22A—C22—H22B | 109.5 |
C8—C9—C13 | 120.66 (19) | H22A—C22—H22C | 109.5 |
C10—C9—C13 | 120.95 (19) | H22B—C22—H22C | 109.5 |
C9—C10—H10 | 119.0 | C20—C23—H23A | 109.5 |
C11—C10—C9 | 121.95 (19) | C20—C23—H23B | 109.5 |
C11—C10—H10 | 119.0 | C20—C23—H23C | 109.5 |
C6—C11—C14 | 122.70 (17) | H23A—C23—H23B | 109.5 |
C10—C11—C6 | 118.00 (18) | H23A—C23—H23C | 109.5 |
C10—C11—C14 | 119.28 (18) | H23B—C23—H23C | 109.5 |
C7—C12—H12A | 109.5 | ||
I1—Se1—C1—N1 | −41.46 (18) | C6—N1—C2—C3 | −98.8 (2) |
I1—Se1—C1—N2 | 140.31 (13) | C6—C7—C8—C9 | −0.1 (3) |
N1—C2—C3—C4 | −50.7 (2) | C7—C6—C11—C10 | −3.4 (3) |
N1—C6—C7—C8 | 179.68 (17) | C7—C6—C11—C14 | 175.07 (19) |
N1—C6—C7—C12 | −1.6 (3) | C7—C8—C9—C10 | −2.0 (3) |
N1—C6—C11—C10 | 179.81 (17) | C7—C8—C9—C13 | 176.87 (19) |
N1—C6—C11—C14 | −1.7 (3) | C8—C9—C10—C11 | 1.4 (3) |
N2—C15—C16—C17 | −179.11 (18) | C9—C10—C11—C6 | 1.2 (3) |
N2—C15—C16—C21 | 3.3 (3) | C9—C10—C11—C14 | −177.31 (19) |
N2—C15—C20—C19 | −179.96 (17) | C11—C6—C7—C8 | 2.8 (3) |
N2—C15—C20—C23 | −1.6 (3) | C11—C6—C7—C12 | −178.41 (19) |
C1—N1—C2—C3 | 84.0 (2) | C12—C7—C8—C9 | −178.89 (19) |
C1—N1—C6—C7 | 111.8 (2) | C13—C9—C10—C11 | −177.44 (19) |
C1—N1—C6—C11 | −71.3 (3) | C15—N2—C1—Se1 | −23.4 (2) |
C1—N2—C5—C4 | −24.0 (3) | C15—N2—C1—N1 | 158.31 (18) |
C1—N2—C15—C16 | −79.9 (2) | C15—N2—C5—C4 | 156.80 (18) |
C1—N2—C15—C20 | 102.1 (2) | C15—C16—C17—C18 | −0.4 (3) |
C2—N1—C1—Se1 | 163.19 (15) | C16—C15—C20—C19 | 2.1 (3) |
C2—N1—C1—N2 | −18.7 (3) | C16—C15—C20—C23 | −179.51 (19) |
C2—N1—C6—C7 | −65.4 (2) | C16—C17—C18—C19 | 0.9 (3) |
C2—N1—C6—C11 | 111.5 (2) | C16—C17—C18—C22 | −178.9 (2) |
C2—C3—C4—C5 | −34.7 (2) | C17—C18—C19—C20 | 0.1 (3) |
C3—C4—C5—N2 | 76.8 (2) | C18—C19—C20—C15 | −1.5 (3) |
C5—N2—C1—Se1 | 157.43 (16) | C18—C19—C20—C23 | −180.0 (2) |
C5—N2—C1—N1 | −20.8 (3) | C20—C15—C16—C17 | −1.1 (3) |
C5—N2—C15—C16 | 99.3 (2) | C20—C15—C16—C21 | −178.7 (2) |
C5—N2—C15—C20 | −78.7 (2) | C21—C16—C17—C18 | 177.2 (2) |
C6—N1—C1—Se1 | −13.8 (3) | C22—C18—C19—C20 | 179.9 (2) |
C6—N1—C1—N2 | 164.29 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2A···I1i | 0.99 | 3.08 | 3.885 (2) | 139 |
C3—H3B···I2ii | 0.99 | 3.14 | 4.007 (2) | 147 |
C5—H5B···I1i | 0.99 | 3.11 | 4.067 (2) | 164 |
Symmetry codes: (i) x+1, y, z; (ii) x+1, y−1, z. |
2(C23H30I2N2S)·2(I2) | Z = 1 |
Mr = 1748.30 | F(000) = 820 |
Triclinic, P1 | Dx = 2.062 Mg m−3 |
a = 8.3022 (9) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.3510 (11) Å | Cell parameters from 71058 reflections |
c = 15.5656 (16) Å | θ = 2.2–30.1° |
α = 83.691 (4)° | µ = 4.51 mm−1 |
β = 87.180 (4)° | T = 100 K |
γ = 75.024 (4)° | Plank, red |
V = 1408.1 (3) Å3 | 0.19 × 0.09 × 0.04 mm |
Bruker D8 Venture Photon 2 diffractometer | 7603 reflections with I > 2σ(I) |
Radiation source: Incoatec IµS | Rint = 0.035 |
φ and ω scans | θmax = 30.1°, θmin = 2.2° |
Absorption correction: multi-scan SADABS v2016/2 (Bruker AXS Inc., 2017) | h = −11→11 |
Tmin = 0.579, Tmax = 0.746 | k = −15→15 |
71058 measured reflections | l = −21→21 |
8260 independent reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.017 | H-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 reflections | Δρmax = 0.50 e Å−3 |
277 parameters | Δρmin = −0.74 e Å−3 |
0 restraints |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
I1 | 0.31247 (2) | 0.58104 (2) | 0.72662 (2) | 0.01485 (3) | |
I2 | 0.10499 (2) | 0.81980 (2) | 0.79506 (2) | 0.02312 (3) | |
S1 | 0.48485 (5) | 0.37844 (4) | 0.68562 (3) | 0.01452 (8) | |
N1 | 0.77284 (18) | 0.42648 (13) | 0.72581 (9) | 0.0121 (3) | |
N2 | 0.70824 (18) | 0.25045 (13) | 0.79742 (10) | 0.0124 (3) | |
C1 | 0.6709 (2) | 0.35257 (15) | 0.74190 (11) | 0.0120 (3) | |
C2 | 0.9150 (2) | 0.41687 (16) | 0.78278 (12) | 0.0145 (3) | |
H2A | 0.879573 | 0.401677 | 0.843769 | 0.017* | |
H2B | 0.947045 | 0.495588 | 0.776116 | 0.017* | |
C3 | 1.0651 (2) | 0.31443 (17) | 0.76182 (13) | 0.0172 (3) | |
H3A | 1.150861 | 0.303678 | 0.806012 | 0.021* | |
H3B | 1.113839 | 0.337002 | 0.705007 | 0.021* | |
C4 | 1.0164 (2) | 0.19328 (16) | 0.75944 (12) | 0.0158 (3) | |
H4A | 0.978858 | 0.189301 | 0.700675 | 0.019* | |
H4B | 1.115986 | 0.124249 | 0.771265 | 0.019* | |
C5 | 0.8792 (2) | 0.17845 (16) | 0.82443 (12) | 0.0158 (3) | |
H5A | 0.880415 | 0.090566 | 0.834195 | 0.019* | |
H5B | 0.903450 | 0.204181 | 0.880113 | 0.019* | |
C6 | 0.7473 (2) | 0.52375 (16) | 0.65478 (11) | 0.0132 (3) | |
C7 | 0.7003 (2) | 0.64546 (16) | 0.67572 (12) | 0.0150 (3) | |
C8 | 0.6790 (2) | 0.73859 (17) | 0.60760 (13) | 0.0178 (3) | |
H8 | 0.646832 | 0.821473 | 0.620441 | 0.021* | |
C9 | 0.7031 (2) | 0.71437 (17) | 0.52180 (12) | 0.0184 (4) | |
C10 | 0.7531 (2) | 0.59230 (17) | 0.50401 (12) | 0.0173 (3) | |
H10 | 0.772011 | 0.574714 | 0.445544 | 0.021* | |
C11 | 0.7763 (2) | 0.49498 (16) | 0.56929 (12) | 0.0147 (3) | |
C12 | 0.6723 (2) | 0.68036 (17) | 0.76724 (12) | 0.0183 (4) | |
H12A | 0.652467 | 0.610928 | 0.805702 | 0.027* | |
H12B | 0.575198 | 0.750766 | 0.769518 | 0.027* | |
H12C | 0.771115 | 0.702017 | 0.785849 | 0.027* | |
C13 | 0.6764 (3) | 0.81838 (19) | 0.45019 (14) | 0.0286 (5) | |
H13A | 0.774137 | 0.852266 | 0.444659 | 0.043* | |
H13B | 0.577350 | 0.882600 | 0.463880 | 0.043* | |
H13C | 0.660499 | 0.787714 | 0.395607 | 0.043* | |
C14 | 0.8295 (3) | 0.36548 (17) | 0.54486 (13) | 0.0201 (4) | |
H14A | 0.733583 | 0.329626 | 0.550029 | 0.030* | |
H14B | 0.917088 | 0.316675 | 0.583581 | 0.030* | |
H14C | 0.872482 | 0.365931 | 0.485078 | 0.030* | |
C15 | 0.5758 (2) | 0.20126 (16) | 0.83975 (11) | 0.0124 (3) | |
C16 | 0.5412 (2) | 0.09825 (16) | 0.81058 (11) | 0.0132 (3) | |
C17 | 0.4238 (2) | 0.04684 (16) | 0.85725 (12) | 0.0156 (3) | |
H17 | 0.398277 | −0.022819 | 0.838184 | 0.019* | |
C18 | 0.3431 (2) | 0.09504 (17) | 0.93107 (12) | 0.0155 (3) | |
C19 | 0.3811 (2) | 0.19780 (17) | 0.95803 (12) | 0.0164 (3) | |
H19 | 0.326392 | 0.231434 | 1.008190 | 0.020* | |
C20 | 0.4973 (2) | 0.25261 (16) | 0.91329 (12) | 0.0149 (3) | |
C21 | 0.6261 (2) | 0.04315 (17) | 0.73114 (12) | 0.0179 (3) | |
H21A | 0.651908 | 0.107845 | 0.689961 | 0.027* | |
H21B | 0.551959 | 0.003877 | 0.704275 | 0.027* | |
H21C | 0.729574 | −0.018074 | 0.747544 | 0.027* | |
C22 | 0.2200 (2) | 0.03633 (19) | 0.98208 (13) | 0.0204 (4) | |
H22A | 0.277600 | −0.021930 | 1.028818 | 0.031* | |
H22B | 0.170277 | −0.007021 | 0.943838 | 0.031* | |
H22C | 0.132084 | 0.099815 | 1.006728 | 0.031* | |
C23 | 0.5348 (3) | 0.36361 (18) | 0.94498 (13) | 0.0209 (4) | |
H23A | 0.653924 | 0.345900 | 0.956892 | 0.031* | |
H23B | 0.469576 | 0.383619 | 0.998038 | 0.031* | |
H23C | 0.505129 | 0.433311 | 0.900567 | 0.031* | |
I3 | 0.02911 (2) | 0.94288 (2) | 0.58243 (2) | 0.02671 (3) | |
I4 | 0.03703 (2) | 0.59671 (2) | 0.94795 (2) | 0.02033 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
I1 | 0.01177 (5) | 0.01314 (5) | 0.01889 (6) | −0.00229 (4) | −0.00107 (4) | −0.00022 (4) |
I2 | 0.02082 (6) | 0.01405 (6) | 0.03315 (7) | −0.00142 (5) | 0.00298 (5) | −0.00554 (5) |
S1 | 0.01187 (18) | 0.01179 (18) | 0.0202 (2) | −0.00258 (15) | −0.00434 (15) | −0.00206 (15) |
N1 | 0.0128 (7) | 0.0105 (6) | 0.0135 (7) | −0.0038 (5) | −0.0023 (5) | −0.0006 (5) |
N2 | 0.0093 (6) | 0.0114 (6) | 0.0161 (7) | −0.0025 (5) | −0.0001 (5) | 0.0007 (5) |
C1 | 0.0116 (7) | 0.0117 (7) | 0.0128 (7) | −0.0024 (6) | −0.0003 (6) | −0.0035 (6) |
C2 | 0.0141 (8) | 0.0137 (8) | 0.0169 (8) | −0.0050 (6) | −0.0056 (6) | −0.0008 (6) |
C3 | 0.0126 (8) | 0.0168 (8) | 0.0224 (9) | −0.0046 (6) | −0.0023 (7) | 0.0006 (7) |
C4 | 0.0105 (7) | 0.0144 (8) | 0.0217 (9) | −0.0020 (6) | −0.0011 (6) | −0.0005 (7) |
C5 | 0.0120 (8) | 0.0137 (8) | 0.0201 (9) | −0.0015 (6) | −0.0022 (6) | 0.0021 (6) |
C6 | 0.0131 (8) | 0.0109 (7) | 0.0162 (8) | −0.0047 (6) | −0.0020 (6) | 0.0004 (6) |
C7 | 0.0154 (8) | 0.0126 (8) | 0.0185 (8) | −0.0054 (6) | −0.0016 (6) | −0.0032 (6) |
C8 | 0.0205 (9) | 0.0114 (8) | 0.0221 (9) | −0.0051 (7) | −0.0025 (7) | −0.0012 (7) |
C9 | 0.0211 (9) | 0.0159 (8) | 0.0191 (9) | −0.0073 (7) | −0.0034 (7) | 0.0028 (7) |
C10 | 0.0207 (9) | 0.0180 (9) | 0.0144 (8) | −0.0070 (7) | −0.0029 (7) | −0.0004 (7) |
C11 | 0.0147 (8) | 0.0139 (8) | 0.0160 (8) | −0.0042 (6) | −0.0011 (6) | −0.0014 (6) |
C12 | 0.0225 (9) | 0.0145 (8) | 0.0194 (9) | −0.0059 (7) | 0.0004 (7) | −0.0054 (7) |
C13 | 0.0453 (13) | 0.0180 (9) | 0.0234 (10) | −0.0113 (9) | −0.0081 (9) | 0.0051 (8) |
C14 | 0.0259 (10) | 0.0163 (9) | 0.0179 (9) | −0.0040 (7) | 0.0011 (7) | −0.0045 (7) |
C15 | 0.0104 (7) | 0.0124 (7) | 0.0138 (8) | −0.0026 (6) | 0.0000 (6) | 0.0004 (6) |
C16 | 0.0130 (8) | 0.0114 (7) | 0.0141 (8) | −0.0014 (6) | −0.0016 (6) | 0.0001 (6) |
C17 | 0.0132 (8) | 0.0116 (8) | 0.0221 (9) | −0.0039 (6) | −0.0033 (7) | 0.0003 (6) |
C18 | 0.0109 (8) | 0.0169 (8) | 0.0175 (8) | −0.0032 (6) | −0.0012 (6) | 0.0035 (6) |
C19 | 0.0134 (8) | 0.0182 (8) | 0.0167 (8) | −0.0023 (7) | 0.0004 (6) | −0.0021 (7) |
C20 | 0.0126 (8) | 0.0145 (8) | 0.0173 (8) | −0.0024 (6) | −0.0019 (6) | −0.0016 (6) |
C21 | 0.0194 (9) | 0.0144 (8) | 0.0198 (9) | −0.0033 (7) | 0.0016 (7) | −0.0053 (7) |
C22 | 0.0155 (8) | 0.0228 (9) | 0.0224 (9) | −0.0074 (7) | 0.0016 (7) | 0.0048 (7) |
C23 | 0.0222 (9) | 0.0209 (9) | 0.0221 (9) | −0.0078 (7) | 0.0013 (7) | −0.0084 (7) |
I3 | 0.03372 (8) | 0.02322 (7) | 0.02649 (7) | −0.01250 (6) | 0.00947 (5) | −0.00872 (5) |
I4 | 0.01638 (6) | 0.02723 (7) | 0.01854 (6) | −0.00494 (5) | −0.00107 (4) | −0.00853 (5) |
I1—I2 | 3.0803 (3) | C12—H12A | 0.9800 |
I1—S1 | 2.5053 (5) | C12—H12B | 0.9800 |
S1—C1 | 1.7559 (18) | C12—H12C | 0.9800 |
N1—C1 | 1.335 (2) | C13—H13A | 0.9800 |
N1—C2 | 1.485 (2) | C13—H13B | 0.9800 |
N1—C6 | 1.456 (2) | C13—H13C | 0.9800 |
N2—C1 | 1.344 (2) | C14—H14A | 0.9800 |
N2—C5 | 1.498 (2) | C14—H14B | 0.9800 |
N2—C15 | 1.456 (2) | C14—H14C | 0.9800 |
C2—H2A | 0.9900 | C15—C16 | 1.400 (2) |
C2—H2B | 0.9900 | C15—C20 | 1.397 (2) |
C2—C3 | 1.519 (3) | C16—C17 | 1.396 (2) |
C3—H3A | 0.9900 | C16—C21 | 1.508 (2) |
C3—H3B | 0.9900 | C17—H17 | 0.9500 |
C3—C4 | 1.535 (3) | C17—C18 | 1.393 (3) |
C4—H4A | 0.9900 | C18—C19 | 1.395 (3) |
C4—H4B | 0.9900 | C18—C22 | 1.509 (2) |
C4—C5 | 1.516 (3) | C19—H19 | 0.9500 |
C5—H5A | 0.9900 | C19—C20 | 1.397 (2) |
C5—H5B | 0.9900 | C20—C23 | 1.510 (3) |
C6—C7 | 1.405 (2) | C21—H21A | 0.9800 |
C6—C11 | 1.400 (2) | C21—H21B | 0.9800 |
C7—C8 | 1.396 (3) | C21—H21C | 0.9800 |
C7—C12 | 1.511 (3) | C22—H22A | 0.9800 |
C8—H8 | 0.9500 | C22—H22B | 0.9800 |
C8—C9 | 1.388 (3) | C22—H22C | 0.9800 |
C9—C10 | 1.394 (3) | C23—H23A | 0.9800 |
C9—C13 | 1.512 (3) | C23—H23B | 0.9800 |
C10—H10 | 0.9500 | C23—H23C | 0.9800 |
C10—C11 | 1.397 (2) | I3—I3i | 2.7507 (4) |
C11—C14 | 1.507 (3) | I4—I4ii | 2.7645 (3) |
S1—I1—I2 | 174.564 (12) | C7—C12—H12B | 109.5 |
C1—S1—I1 | 104.65 (6) | C7—C12—H12C | 109.5 |
C1—N1—C2 | 121.09 (14) | H12A—C12—H12B | 109.5 |
C1—N1—C6 | 122.46 (15) | H12A—C12—H12C | 109.5 |
C6—N1—C2 | 116.39 (13) | H12B—C12—H12C | 109.5 |
C1—N2—C5 | 126.41 (14) | C9—C13—H13A | 109.5 |
C1—N2—C15 | 120.30 (14) | C9—C13—H13B | 109.5 |
C15—N2—C5 | 113.27 (13) | C9—C13—H13C | 109.5 |
N1—C1—S1 | 121.32 (13) | H13A—C13—H13B | 109.5 |
N1—C1—N2 | 122.70 (16) | H13A—C13—H13C | 109.5 |
N2—C1—S1 | 115.85 (12) | H13B—C13—H13C | 109.5 |
N1—C2—H2A | 109.2 | C11—C14—H14A | 109.5 |
N1—C2—H2B | 109.2 | C11—C14—H14B | 109.5 |
N1—C2—C3 | 111.99 (15) | C11—C14—H14C | 109.5 |
H2A—C2—H2B | 107.9 | H14A—C14—H14B | 109.5 |
C3—C2—H2A | 109.2 | H14A—C14—H14C | 109.5 |
C3—C2—H2B | 109.2 | H14B—C14—H14C | 109.5 |
C2—C3—H3A | 109.4 | C16—C15—N2 | 119.45 (15) |
C2—C3—H3B | 109.4 | C20—C15—N2 | 118.26 (15) |
C2—C3—C4 | 111.23 (15) | C20—C15—C16 | 122.05 (16) |
H3A—C3—H3B | 108.0 | C15—C16—C21 | 121.90 (16) |
C4—C3—H3A | 109.4 | C17—C16—C15 | 118.02 (16) |
C4—C3—H3B | 109.4 | C17—C16—C21 | 120.08 (16) |
C3—C4—H4A | 109.0 | C16—C17—H17 | 119.1 |
C3—C4—H4B | 109.0 | C18—C17—C16 | 121.70 (17) |
H4A—C4—H4B | 107.8 | C18—C17—H17 | 119.1 |
C5—C4—C3 | 112.93 (16) | C17—C18—C19 | 118.53 (16) |
C5—C4—H4A | 109.0 | C17—C18—C22 | 121.01 (17) |
C5—C4—H4B | 109.0 | C19—C18—C22 | 120.45 (17) |
N2—C5—C4 | 114.08 (14) | C18—C19—H19 | 119.1 |
N2—C5—H5A | 108.7 | C18—C19—C20 | 121.81 (17) |
N2—C5—H5B | 108.7 | C20—C19—H19 | 119.1 |
C4—C5—H5A | 108.7 | C15—C20—C19 | 117.88 (16) |
C4—C5—H5B | 108.7 | C15—C20—C23 | 122.14 (16) |
H5A—C5—H5B | 107.6 | C19—C20—C23 | 119.98 (17) |
C7—C6—N1 | 117.67 (15) | C16—C21—H21A | 109.5 |
C11—C6—N1 | 120.20 (15) | C16—C21—H21B | 109.5 |
C11—C6—C7 | 122.07 (16) | C16—C21—H21C | 109.5 |
C6—C7—C12 | 123.71 (16) | H21A—C21—H21B | 109.5 |
C8—C7—C6 | 117.60 (17) | H21A—C21—H21C | 109.5 |
C8—C7—C12 | 118.70 (16) | H21B—C21—H21C | 109.5 |
C7—C8—H8 | 118.8 | C18—C22—H22A | 109.5 |
C9—C8—C7 | 122.31 (17) | C18—C22—H22B | 109.5 |
C9—C8—H8 | 118.8 | C18—C22—H22C | 109.5 |
C8—C9—C10 | 118.20 (17) | H22A—C22—H22B | 109.5 |
C8—C9—C13 | 120.37 (18) | H22A—C22—H22C | 109.5 |
C10—C9—C13 | 121.43 (18) | H22B—C22—H22C | 109.5 |
C9—C10—H10 | 118.9 | C20—C23—H23A | 109.5 |
C9—C10—C11 | 122.22 (17) | C20—C23—H23B | 109.5 |
C11—C10—H10 | 118.9 | C20—C23—H23C | 109.5 |
C6—C11—C14 | 123.33 (16) | H23A—C23—H23B | 109.5 |
C10—C11—C6 | 117.58 (16) | H23A—C23—H23C | 109.5 |
C10—C11—C14 | 119.09 (16) | H23B—C23—H23C | 109.5 |
C7—C12—H12A | 109.5 | ||
I1—S1—C1—N1 | −63.56 (15) | C6—N1—C2—C3 | −101.40 (17) |
I1—S1—C1—N2 | 120.48 (12) | C6—C7—C8—C9 | −0.3 (3) |
N1—C2—C3—C4 | −51.4 (2) | C7—C6—C11—C10 | −1.5 (3) |
N1—C6—C7—C8 | 178.79 (16) | C7—C6—C11—C14 | 178.94 (17) |
N1—C6—C7—C12 | −1.1 (3) | C7—C8—C9—C10 | −1.1 (3) |
N1—C6—C11—C10 | −178.63 (16) | C7—C8—C9—C13 | 179.24 (19) |
N1—C6—C11—C14 | 1.8 (3) | C8—C9—C10—C11 | 1.2 (3) |
N2—C15—C16—C17 | 174.43 (15) | C9—C10—C11—C6 | 0.1 (3) |
N2—C15—C16—C21 | −5.8 (3) | C9—C10—C11—C14 | 179.67 (18) |
N2—C15—C20—C19 | −174.33 (16) | C11—C6—C7—C8 | 1.6 (3) |
N2—C15—C20—C23 | 5.5 (3) | C11—C6—C7—C12 | −178.32 (17) |
C1—N1—C2—C3 | 81.3 (2) | C12—C7—C8—C9 | 179.64 (18) |
C1—N1—C6—C7 | 111.24 (19) | C13—C9—C10—C11 | −179.15 (19) |
C1—N1—C6—C11 | −71.5 (2) | C15—N2—C1—S1 | −29.4 (2) |
C1—N2—C5—C4 | −24.7 (2) | C15—N2—C1—N1 | 154.74 (16) |
C1—N2—C15—C16 | 103.38 (19) | C15—N2—C5—C4 | 156.97 (15) |
C1—N2—C15—C20 | −82.1 (2) | C15—C16—C17—C18 | −0.4 (3) |
C2—N1—C1—S1 | 169.88 (13) | C16—C15—C20—C19 | 0.0 (3) |
C2—N1—C1—N2 | −14.4 (3) | C16—C15—C20—C23 | 179.88 (17) |
C2—N1—C6—C7 | −66.0 (2) | C16—C17—C18—C19 | 0.4 (3) |
C2—N1—C6—C11 | 111.30 (18) | C16—C17—C18—C22 | −178.36 (17) |
C2—C3—C4—C5 | −34.2 (2) | C17—C18—C19—C20 | −0.2 (3) |
C3—C4—C5—N2 | 77.8 (2) | C18—C19—C20—C15 | 0.0 (3) |
C5—N2—C1—S1 | 152.39 (14) | C18—C19—C20—C23 | −179.86 (17) |
C5—N2—C1—N1 | −23.5 (3) | C20—C15—C16—C17 | 0.1 (3) |
C5—N2—C15—C16 | −78.2 (2) | C20—C15—C16—C21 | 179.95 (17) |
C5—N2—C15—C20 | 96.35 (19) | C21—C16—C17—C18 | 179.84 (17) |
C6—N1—C1—S1 | −7.2 (2) | C22—C18—C19—C20 | 178.55 (17) |
C6—N1—C1—N2 | 168.47 (16) |
Symmetry codes: (i) −x, −y+2, −z+1; (ii) −x, −y+1, −z+2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2B···I4iii | 0.99 | 3.22 | 3.7794 (18) | 118 |
C5—H5A···I2iv | 0.99 | 3.26 | 4.0837 (19) | 142 |
Symmetry codes: (iii) x+1, y, z; (iv) x+1, y−1, z. |
C23H30IN2Se·I3 | F(000) = 1712 |
Mr = 921.05 | Dx = 2.183 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 11.0063 (7) Å | Cell parameters from 9954 reflections |
b = 22.9632 (14) Å | θ = 2.5–27.5° |
c = 11.1015 (6) Å | µ = 5.76 mm−1 |
β = 93.024 (2)° | T = 100 K |
V = 2801.9 (3) Å3 | Plate, red |
Z = 4 | 0.06 × 0.06 × 0.02 mm |
Bruker D8 Venture Photon 2 diffractometer | 5536 reflections with I > 2σ(I) |
Radiation source: Incoatec IµS | Rint = 0.091 |
φ and ω scans | θmax = 27.5°, θmin = 2.1° |
Absorption correction: multi-scan SADABS v2016/2 (Bruker AXS Inc., 2017) | h = −12→14 |
Tmin = 0.606, Tmax = 0.746 | k = −29→29 |
36709 measured reflections | l = −13→14 |
6428 independent reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.062 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.127 | H-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 parameters | Δρmax = 2.17 e Å−3 |
30 restraints | Δρmin = −1.40 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refined as a 2-component twin. |
x | y | z | Uiso*/Ueq | ||
I1 | 0.59561 (6) | 0.64902 (3) | 0.81087 (6) | 0.01566 (15) | |
Se1 | 0.40931 (11) | 0.71085 (5) | 0.86165 (11) | 0.0219 (3) | |
N1 | 0.2695 (8) | 0.6471 (4) | 0.6789 (7) | 0.0128 (17) | |
N2 | 0.2234 (8) | 0.7464 (4) | 0.7042 (8) | 0.0134 (17) | |
C1 | 0.2883 (9) | 0.6986 (4) | 0.7330 (9) | 0.0106 (19) | |
C2 | 0.2029 (10) | 0.6450 (5) | 0.5580 (9) | 0.020 (2) | |
H2A | 0.226802 | 0.609281 | 0.515278 | 0.024* | |
H2B | 0.227365 | 0.678895 | 0.509738 | 0.024* | |
C3 | 0.0654 (10) | 0.6455 (5) | 0.5662 (10) | 0.019 (2) | |
H3A | 0.026628 | 0.647727 | 0.483796 | 0.023* | |
H3B | 0.039505 | 0.608654 | 0.603149 | 0.023* | |
C4 | 0.0220 (10) | 0.6962 (4) | 0.6399 (9) | 0.014 (2) | |
H4A | 0.020130 | 0.684114 | 0.725381 | 0.017* | |
H4B | −0.062112 | 0.706380 | 0.611500 | 0.017* | |
C5 | 0.1018 (10) | 0.7498 (5) | 0.6320 (10) | 0.019 (2) | |
H5A | 0.056192 | 0.783871 | 0.660497 | 0.022* | |
H5B | 0.117801 | 0.756659 | 0.546226 | 0.022* | |
C6 | 0.3091 (10) | 0.5925 (4) | 0.7319 (9) | 0.0133 (17) | |
C7 | 0.3935 (9) | 0.5589 (4) | 0.6712 (9) | 0.0128 (16) | |
C8 | 0.4292 (10) | 0.5065 (4) | 0.7216 (9) | 0.0141 (18) | |
H8 | 0.486185 | 0.483288 | 0.681713 | 0.017* | |
C9 | 0.3842 (10) | 0.4860 (5) | 0.8301 (10) | 0.017 (2) | |
C10 | 0.2992 (10) | 0.5200 (5) | 0.8848 (9) | 0.017 (2) | |
H10 | 0.266542 | 0.506303 | 0.957084 | 0.021* | |
C11 | 0.2594 (9) | 0.5735 (4) | 0.8382 (9) | 0.013 (2) | |
C12 | 0.4501 (10) | 0.5785 (5) | 0.5575 (10) | 0.018 (2) | |
H12A | 0.536370 | 0.567731 | 0.561145 | 0.028* | |
H12B | 0.442353 | 0.620851 | 0.549616 | 0.028* | |
H12C | 0.408392 | 0.559617 | 0.487780 | 0.028* | |
C13 | 0.4292 (11) | 0.4289 (5) | 0.8833 (11) | 0.025 (3) | |
H13A | 0.496964 | 0.436212 | 0.942209 | 0.037* | |
H13B | 0.456930 | 0.403765 | 0.818850 | 0.037* | |
H13C | 0.362957 | 0.409560 | 0.923392 | 0.037* | |
C14 | 0.1644 (11) | 0.6067 (5) | 0.9025 (10) | 0.021 (2) | |
H14A | 0.125240 | 0.580667 | 0.958705 | 0.032* | |
H14B | 0.103164 | 0.621865 | 0.843354 | 0.032* | |
H14C | 0.202941 | 0.639129 | 0.947300 | 0.032* | |
C15 | 0.2641 (9) | 0.8031 (4) | 0.7498 (9) | 0.013 (2) | |
C16 | 0.3472 (9) | 0.8346 (4) | 0.6817 (9) | 0.013 (2) | |
C17 | 0.3851 (10) | 0.8889 (5) | 0.7275 (10) | 0.0174 (18) | |
H17 | 0.440907 | 0.911377 | 0.684410 | 0.021* | |
C18 | 0.3424 (10) | 0.9111 (5) | 0.8364 (10) | 0.0177 (14) | |
C19 | 0.2600 (10) | 0.8784 (5) | 0.8961 (10) | 0.0168 (18) | |
H19 | 0.229178 | 0.893885 | 0.967695 | 0.020* | |
C20 | 0.2194 (10) | 0.8242 (5) | 0.8575 (10) | 0.017 (2) | |
C21 | 0.3973 (11) | 0.8098 (5) | 0.5704 (10) | 0.023 (2) | |
H21A | 0.461063 | 0.781480 | 0.592938 | 0.034* | |
H21B | 0.431815 | 0.841235 | 0.523107 | 0.034* | |
H21C | 0.332025 | 0.790525 | 0.522082 | 0.034* | |
C22 | 0.3888 (10) | 0.9692 (4) | 0.8813 (10) | 0.0178 (15) | |
H22A | 0.477567 | 0.970319 | 0.878506 | 0.027* | |
H22B | 0.365873 | 0.975012 | 0.964630 | 0.027* | |
H22C | 0.353012 | 1.000216 | 0.830164 | 0.027* | |
C23 | 0.1302 (10) | 0.7901 (5) | 0.9276 (10) | 0.021 (2) | |
H23A | 0.049295 | 0.792481 | 0.886632 | 0.031* | |
H23B | 0.127291 | 0.806367 | 1.009002 | 0.031* | |
H23C | 0.155977 | 0.749298 | 0.932788 | 0.031* | |
I2 | 0.82187 (7) | 0.56569 (3) | 0.76383 (8) | 0.02662 (19) | |
I3 | 0.76938 (6) | 0.43650 (3) | 0.76074 (6) | 0.01781 (16) | |
I4 | 0.73525 (8) | 0.31356 (3) | 0.76667 (7) | 0.02759 (19) |
U11 | U22 | U33 | U12 | U13 | U23 | |
I1 | 0.0164 (3) | 0.0133 (3) | 0.0168 (3) | −0.0016 (3) | −0.0037 (2) | −0.0004 (3) |
Se1 | 0.0208 (6) | 0.0211 (6) | 0.0225 (6) | 0.0077 (5) | −0.0115 (5) | −0.0126 (4) |
N1 | 0.018 (4) | 0.008 (4) | 0.012 (4) | 0.001 (3) | −0.003 (3) | 0.004 (3) |
N2 | 0.014 (4) | 0.007 (4) | 0.018 (4) | 0.001 (3) | −0.005 (3) | 0.002 (3) |
C1 | 0.006 (4) | 0.013 (5) | 0.013 (5) | −0.002 (4) | 0.004 (4) | 0.001 (4) |
C2 | 0.025 (6) | 0.022 (6) | 0.013 (5) | −0.009 (5) | 0.002 (4) | −0.006 (4) |
C3 | 0.025 (6) | 0.013 (5) | 0.019 (5) | −0.004 (4) | −0.005 (5) | 0.005 (4) |
C4 | 0.019 (5) | 0.009 (5) | 0.014 (5) | −0.005 (4) | −0.006 (4) | 0.000 (4) |
C5 | 0.017 (5) | 0.017 (5) | 0.021 (5) | 0.000 (4) | −0.003 (4) | 0.002 (4) |
C6 | 0.014 (4) | 0.012 (4) | 0.014 (4) | 0.000 (3) | −0.004 (3) | −0.003 (3) |
C7 | 0.013 (3) | 0.011 (3) | 0.015 (3) | 0.000 (3) | −0.002 (3) | −0.006 (3) |
C8 | 0.014 (4) | 0.014 (4) | 0.015 (4) | 0.003 (3) | 0.001 (3) | −0.006 (3) |
C9 | 0.022 (6) | 0.012 (5) | 0.017 (5) | −0.007 (4) | −0.005 (4) | −0.005 (4) |
C10 | 0.018 (5) | 0.021 (6) | 0.013 (5) | −0.007 (4) | −0.002 (4) | −0.003 (4) |
C11 | 0.012 (5) | 0.015 (5) | 0.011 (5) | 0.000 (4) | −0.005 (4) | −0.001 (4) |
C12 | 0.017 (5) | 0.019 (6) | 0.019 (5) | 0.007 (4) | 0.007 (4) | 0.003 (4) |
C13 | 0.019 (6) | 0.026 (6) | 0.029 (6) | −0.003 (5) | −0.010 (5) | −0.003 (5) |
C14 | 0.024 (6) | 0.027 (6) | 0.012 (5) | 0.010 (5) | 0.006 (4) | 0.005 (4) |
C15 | 0.012 (5) | 0.006 (5) | 0.021 (5) | 0.002 (4) | −0.008 (4) | −0.002 (4) |
C16 | 0.015 (5) | 0.014 (5) | 0.011 (5) | −0.001 (4) | 0.003 (4) | −0.004 (4) |
C17 | 0.012 (4) | 0.014 (4) | 0.026 (4) | −0.002 (3) | −0.005 (3) | 0.000 (3) |
C18 | 0.014 (3) | 0.012 (3) | 0.026 (3) | −0.001 (3) | −0.008 (3) | −0.003 (3) |
C19 | 0.017 (4) | 0.013 (4) | 0.020 (4) | 0.000 (3) | −0.006 (3) | −0.002 (3) |
C20 | 0.012 (5) | 0.012 (5) | 0.027 (6) | −0.003 (4) | −0.004 (4) | 0.004 (4) |
C21 | 0.022 (6) | 0.024 (6) | 0.023 (6) | −0.003 (5) | 0.009 (5) | 0.001 (5) |
C22 | 0.014 (3) | 0.012 (3) | 0.027 (3) | −0.002 (3) | −0.008 (3) | −0.003 (3) |
C23 | 0.023 (6) | 0.014 (5) | 0.026 (6) | 0.000 (4) | 0.007 (5) | −0.003 (4) |
I2 | 0.0221 (4) | 0.0214 (4) | 0.0370 (5) | 0.0032 (3) | 0.0071 (3) | −0.0011 (3) |
I3 | 0.0159 (3) | 0.0253 (4) | 0.0121 (3) | 0.0018 (3) | −0.0008 (2) | 0.0001 (3) |
I4 | 0.0392 (5) | 0.0260 (4) | 0.0174 (4) | −0.0077 (3) | −0.0001 (3) | 0.0027 (3) |
I1—Se1 | 2.5806 (13) | C12—H12B | 0.9800 |
Se1—C1 | 1.921 (10) | C12—H12C | 0.9800 |
N1—C1 | 1.339 (13) | C13—H13A | 0.9800 |
N1—C2 | 1.496 (13) | C13—H13B | 0.9800 |
N1—C6 | 1.441 (13) | C13—H13C | 0.9800 |
N2—C1 | 1.339 (13) | C14—H14A | 0.9800 |
N2—C5 | 1.526 (13) | C14—H14B | 0.9800 |
N2—C15 | 1.458 (12) | C14—H14C | 0.9800 |
C2—H2A | 0.9900 | C15—C16 | 1.416 (15) |
C2—H2B | 0.9900 | C15—C20 | 1.402 (16) |
C2—C3 | 1.521 (16) | C16—C17 | 1.402 (14) |
C3—H3A | 0.9900 | C16—C21 | 1.492 (14) |
C3—H3B | 0.9900 | C17—H17 | 0.9500 |
C3—C4 | 1.515 (15) | C17—C18 | 1.415 (16) |
C4—H4A | 0.9900 | C18—C19 | 1.374 (16) |
C4—H4B | 0.9900 | C18—C22 | 1.505 (14) |
C4—C5 | 1.517 (14) | C19—H19 | 0.9500 |
C5—H5A | 0.9900 | C19—C20 | 1.383 (15) |
C5—H5B | 0.9900 | C20—C23 | 1.504 (15) |
C6—C7 | 1.407 (14) | C21—H21A | 0.9800 |
C6—C11 | 1.398 (15) | C21—H21B | 0.9800 |
C7—C8 | 1.377 (14) | C21—H21C | 0.9800 |
C7—C12 | 1.505 (14) | C22—H22A | 0.9800 |
C8—H8 | 0.9500 | C22—H22B | 0.9800 |
C8—C9 | 1.407 (15) | C22—H22C | 0.9800 |
C9—C10 | 1.383 (16) | C23—H23A | 0.9800 |
C9—C13 | 1.512 (16) | C23—H23B | 0.9800 |
C10—H10 | 0.9500 | C23—H23C | 0.9800 |
C10—C11 | 1.394 (15) | I2—I3 | 3.0222 (11) |
C11—C14 | 1.503 (14) | I3—I4 | 2.8492 (11) |
C12—H12A | 0.9800 | ||
C1—Se1—I1 | 106.5 (3) | C7—C12—H12C | 109.5 |
C1—N1—C2 | 119.2 (8) | H12A—C12—H12B | 109.5 |
C1—N1—C6 | 123.3 (8) | H12A—C12—H12C | 109.5 |
C6—N1—C2 | 117.5 (8) | H12B—C12—H12C | 109.5 |
C1—N2—C5 | 127.5 (9) | C9—C13—H13A | 109.5 |
C1—N2—C15 | 119.9 (8) | C9—C13—H13B | 109.5 |
C15—N2—C5 | 112.4 (8) | C9—C13—H13C | 109.5 |
N1—C1—Se1 | 123.2 (7) | H13A—C13—H13B | 109.5 |
N2—C1—Se1 | 113.4 (7) | H13A—C13—H13C | 109.5 |
N2—C1—N1 | 123.4 (9) | H13B—C13—H13C | 109.5 |
N1—C2—H2A | 109.0 | C11—C14—H14A | 109.5 |
N1—C2—H2B | 109.0 | C11—C14—H14B | 109.5 |
N1—C2—C3 | 112.9 (9) | C11—C14—H14C | 109.5 |
H2A—C2—H2B | 107.8 | H14A—C14—H14B | 109.5 |
C3—C2—H2A | 109.0 | H14A—C14—H14C | 109.5 |
C3—C2—H2B | 109.0 | H14B—C14—H14C | 109.5 |
C2—C3—H3A | 109.1 | C16—C15—N2 | 117.8 (9) |
C2—C3—H3B | 109.1 | C20—C15—N2 | 119.2 (9) |
H3A—C3—H3B | 107.8 | C20—C15—C16 | 123.0 (9) |
C4—C3—C2 | 112.5 (9) | C15—C16—C21 | 121.6 (9) |
C4—C3—H3A | 109.1 | C17—C16—C15 | 116.7 (9) |
C4—C3—H3B | 109.1 | C17—C16—C21 | 121.6 (10) |
C3—C4—H4A | 109.0 | C16—C17—H17 | 119.2 |
C3—C4—H4B | 109.0 | C16—C17—C18 | 121.6 (10) |
C3—C4—C5 | 113.1 (9) | C18—C17—H17 | 119.2 |
H4A—C4—H4B | 107.8 | C17—C18—C22 | 118.7 (10) |
C5—C4—H4A | 109.0 | C19—C18—C17 | 118.2 (10) |
C5—C4—H4B | 109.0 | C19—C18—C22 | 123.1 (10) |
N2—C5—H5A | 108.5 | C18—C19—H19 | 118.2 |
N2—C5—H5B | 108.5 | C18—C19—C20 | 123.6 (11) |
C4—C5—N2 | 115.0 (9) | C20—C19—H19 | 118.2 |
C4—C5—H5A | 108.5 | C15—C20—C23 | 122.0 (9) |
C4—C5—H5B | 108.5 | C19—C20—C15 | 116.9 (10) |
H5A—C5—H5B | 107.5 | C19—C20—C23 | 121.1 (10) |
C7—C6—N1 | 118.3 (9) | C16—C21—H21A | 109.5 |
C11—C6—N1 | 119.6 (9) | C16—C21—H21B | 109.5 |
C11—C6—C7 | 122.1 (9) | C16—C21—H21C | 109.5 |
C6—C7—C12 | 123.5 (9) | H21A—C21—H21B | 109.5 |
C8—C7—C6 | 117.8 (10) | H21A—C21—H21C | 109.5 |
C8—C7—C12 | 118.7 (9) | H21B—C21—H21C | 109.5 |
C7—C8—H8 | 118.9 | C18—C22—H22A | 109.5 |
C7—C8—C9 | 122.3 (10) | C18—C22—H22B | 109.5 |
C9—C8—H8 | 118.9 | C18—C22—H22C | 109.5 |
C8—C9—C13 | 120.1 (10) | H22A—C22—H22B | 109.5 |
C10—C9—C8 | 117.7 (10) | H22A—C22—H22C | 109.5 |
C10—C9—C13 | 122.2 (10) | H22B—C22—H22C | 109.5 |
C9—C10—H10 | 118.6 | C20—C23—H23A | 109.5 |
C9—C10—C11 | 122.8 (10) | C20—C23—H23B | 109.5 |
C11—C10—H10 | 118.6 | C20—C23—H23C | 109.5 |
C6—C11—C14 | 123.7 (9) | H23A—C23—H23B | 109.5 |
C10—C11—C6 | 117.3 (10) | H23A—C23—H23C | 109.5 |
C10—C11—C14 | 118.9 (9) | H23B—C23—H23C | 109.5 |
C7—C12—H12A | 109.5 | I4—I3—I2 | 176.12 (4) |
C7—C12—H12B | 109.5 | ||
N1—C2—C3—C4 | 53.7 (12) | C6—C7—C8—C9 | 0.0 (15) |
N1—C6—C7—C8 | −179.0 (9) | C7—C6—C11—C10 | 1.7 (15) |
N1—C6—C7—C12 | 3.6 (15) | C7—C6—C11—C14 | −176.9 (10) |
N1—C6—C11—C10 | 179.0 (9) | C7—C8—C9—C10 | 1.5 (15) |
N1—C6—C11—C14 | 0.4 (15) | C7—C8—C9—C13 | −178.2 (9) |
N2—C15—C16—C17 | −179.9 (9) | C8—C9—C10—C11 | −1.5 (15) |
N2—C15—C16—C21 | −3.3 (15) | C9—C10—C11—C6 | −0.1 (15) |
N2—C15—C20—C19 | −179.4 (9) | C9—C10—C11—C14 | 178.6 (10) |
N2—C15—C20—C23 | −0.2 (15) | C11—C6—C7—C8 | −1.7 (15) |
C1—N1—C2—C3 | −83.4 (12) | C11—C6—C7—C12 | −179.1 (10) |
C1—N1—C6—C7 | −118.3 (11) | C12—C7—C8—C9 | 177.6 (10) |
C1—N1—C6—C11 | 64.3 (13) | C13—C9—C10—C11 | 178.3 (9) |
C1—N2—C5—C4 | 28.2 (15) | C15—N2—C1—Se1 | 13.1 (12) |
C1—N2—C15—C16 | 87.2 (12) | C15—N2—C1—N1 | −168.0 (9) |
C1—N2—C15—C20 | −93.2 (12) | C15—N2—C5—C4 | −148.0 (9) |
C2—N1—C1—Se1 | −161.4 (7) | C15—C16—C17—C18 | −0.1 (15) |
C2—N1—C1—N2 | 19.7 (15) | C16—C15—C20—C19 | 0.2 (15) |
C2—N1—C6—C7 | 62.5 (12) | C16—C15—C20—C23 | 179.4 (10) |
C2—N1—C6—C11 | −114.9 (11) | C16—C17—C18—C19 | −1.2 (16) |
C2—C3—C4—C5 | 31.2 (12) | C16—C17—C18—C22 | 178.9 (9) |
C3—C4—C5—N2 | −75.1 (11) | C17—C18—C19—C20 | 2.1 (16) |
C5—N2—C1—Se1 | −162.9 (8) | C18—C19—C20—C15 | −1.6 (16) |
C5—N2—C1—N1 | 16.0 (16) | C18—C19—C20—C23 | 179.2 (10) |
C5—N2—C15—C16 | −96.2 (11) | C20—C15—C16—C17 | 0.6 (15) |
C5—N2—C15—C20 | 83.3 (11) | C20—C15—C16—C21 | 177.2 (10) |
C6—N1—C1—Se1 | 19.4 (14) | C21—C16—C17—C18 | −176.6 (10) |
C6—N1—C1—N2 | −159.4 (10) | C22—C18—C19—C20 | −178.1 (10) |
C6—N1—C2—C3 | 95.8 (11) |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2A···I3i | 0.99 | 3.24 | 4.029 (10) | 138 |
C2—H2B···I4i | 0.99 | 3.12 | 3.823 (11) | 129 |
C3—H3B···I2ii | 0.99 | 3.22 | 3.998 (11) | 137 |
C5—H5B···Se1iii | 0.99 | 3.09 | 3.693 (11) | 121 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x−1, y, z; (iii) x−1/2, −y+3/2, z−1/2. |
C23H30IN2Se·I3·CH2Cl2 | Z = 2 |
Mr = 1005.97 | F(000) = 940 |
Triclinic, P1 | Dx = 2.129 Mg m−3 |
a = 8.4541 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.5353 (4) Å | Cell parameters from 64752 reflections |
c = 22.0045 (11) Å | θ = 2.4–29.6° |
α = 93.258 (2)° | µ = 5.32 mm−1 |
β = 90.198 (2)° | T = 100 K |
γ = 98.032 (2)° | Plate, red |
V = 1569.58 (13) Å3 | 0.24 × 0.15 × 0.05 mm |
Bruker D8 Venture Photon 2 diffractometer | 7994 reflections with I > 2σ(I) |
Radiation source: Incoatec IµS | Rint = 0.038 |
φ and ω scans | θmax = 29.6°, θmin = 2.4° |
Absorption correction: multi-scan SADABS v2016/2 (Bruker AXS Inc., 2017) | h = −11→11 |
Tmin = 0.527, Tmax = 0.746 | k = −11→11 |
64752 measured reflections | l = −30→30 |
8821 independent reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.019 | H-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 reflections | Δρmax = 0.81 e Å−3 |
304 parameters | Δρmin = −0.88 e Å−3 |
0 restraints |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
I1 | 1.08899 (2) | 0.41978 (2) | 0.70459 (2) | 0.01695 (3) | |
I2 | 1.21875 (2) | 0.08963 (2) | 0.67867 (2) | 0.02237 (4) | |
I3 | 1.31997 (2) | 0.08657 (2) | 0.80982 (2) | 0.01745 (3) | |
I4 | 1.42535 (2) | 0.08034 (2) | 0.93236 (2) | 0.02692 (4) | |
Se1 | 0.99525 (2) | 0.69370 (2) | 0.72771 (2) | 0.01595 (4) | |
N1 | 0.7724 (2) | 0.54815 (19) | 0.81139 (8) | 0.0131 (3) | |
N2 | 0.6632 (2) | 0.6679 (2) | 0.73064 (8) | 0.0150 (3) | |
C1 | 0.7875 (2) | 0.6272 (2) | 0.76082 (9) | 0.0133 (4) | |
C2 | 0.6158 (2) | 0.4582 (2) | 0.82727 (10) | 0.0166 (4) | |
H2A | 0.634451 | 0.373252 | 0.854154 | 0.020* | |
H2B | 0.562633 | 0.407149 | 0.789611 | 0.020* | |
C3 | 0.5060 (3) | 0.5616 (3) | 0.85889 (11) | 0.0220 (4) | |
H3A | 0.550320 | 0.598557 | 0.899740 | 0.026* | |
H3B | 0.400136 | 0.498399 | 0.864306 | 0.026* | |
C4 | 0.4862 (3) | 0.7049 (3) | 0.82250 (11) | 0.0225 (5) | |
H4A | 0.381050 | 0.738325 | 0.831890 | 0.027* | |
H4B | 0.569619 | 0.793603 | 0.835772 | 0.027* | |
C5 | 0.4974 (3) | 0.6740 (3) | 0.75456 (10) | 0.0207 (4) | |
H5A | 0.430654 | 0.571824 | 0.742882 | 0.025* | |
H5B | 0.451181 | 0.757966 | 0.734235 | 0.025* | |
C6 | 0.9038 (2) | 0.5457 (2) | 0.85400 (9) | 0.0135 (4) | |
C7 | 0.9539 (2) | 0.3996 (2) | 0.86445 (9) | 0.0135 (4) | |
C8 | 1.0733 (2) | 0.3973 (2) | 0.90838 (9) | 0.0151 (4) | |
H8 | 1.108985 | 0.299323 | 0.915870 | 0.018* | |
C9 | 1.1414 (2) | 0.5337 (3) | 0.94140 (9) | 0.0161 (4) | |
C10 | 1.0874 (3) | 0.6762 (3) | 0.93010 (10) | 0.0178 (4) | |
H10 | 1.133794 | 0.770283 | 0.952279 | 0.021* | |
C11 | 0.9675 (3) | 0.6854 (2) | 0.88728 (9) | 0.0162 (4) | |
C12 | 0.8835 (3) | 0.2452 (2) | 0.83186 (10) | 0.0168 (4) | |
H12A | 0.807145 | 0.185952 | 0.858473 | 0.025* | |
H12B | 0.969092 | 0.182452 | 0.821294 | 0.025* | |
H12C | 0.828454 | 0.266971 | 0.794638 | 0.025* | |
C13 | 1.2663 (3) | 0.5267 (3) | 0.98998 (10) | 0.0217 (4) | |
H13A | 1.214326 | 0.513026 | 1.029443 | 0.032* | |
H13B | 1.341333 | 0.625372 | 0.991958 | 0.032* | |
H13C | 1.324337 | 0.437012 | 0.980085 | 0.032* | |
C14 | 0.9079 (3) | 0.8425 (3) | 0.88093 (11) | 0.0229 (5) | |
H14A | 0.909002 | 0.866989 | 0.837946 | 0.034* | |
H14B | 0.977424 | 0.925885 | 0.904497 | 0.034* | |
H14C | 0.798613 | 0.836435 | 0.896212 | 0.034* | |
C15 | 0.6763 (2) | 0.7079 (2) | 0.66740 (9) | 0.0147 (4) | |
C16 | 0.6542 (3) | 0.5839 (3) | 0.62244 (10) | 0.0178 (4) | |
C17 | 0.6543 (3) | 0.6254 (3) | 0.56198 (10) | 0.0233 (5) | |
H17 | 0.642023 | 0.543807 | 0.530408 | 0.028* | |
C18 | 0.6719 (3) | 0.7830 (3) | 0.54662 (10) | 0.0241 (5) | |
C19 | 0.6949 (3) | 0.9021 (3) | 0.59294 (10) | 0.0213 (4) | |
H19 | 0.709395 | 1.009704 | 0.582674 | 0.026* | |
C20 | 0.6971 (2) | 0.8674 (2) | 0.65402 (10) | 0.0162 (4) | |
C21 | 0.6309 (3) | 0.4128 (3) | 0.63782 (11) | 0.0247 (5) | |
H21A | 0.714928 | 0.394842 | 0.666333 | 0.037* | |
H21B | 0.636270 | 0.345259 | 0.600560 | 0.037* | |
H21C | 0.526228 | 0.386796 | 0.656579 | 0.037* | |
C22 | 0.6606 (4) | 0.8253 (4) | 0.48136 (12) | 0.0380 (6) | |
H22A | 0.554214 | 0.853182 | 0.473341 | 0.057* | |
H22B | 0.678532 | 0.734368 | 0.454306 | 0.057* | |
H22C | 0.741732 | 0.915769 | 0.473972 | 0.057* | |
C23 | 0.7241 (3) | 0.9986 (3) | 0.70328 (10) | 0.0214 (4) | |
H23A | 0.628302 | 0.996965 | 0.728325 | 0.032* | |
H23B | 0.746331 | 1.100933 | 0.684690 | 0.032* | |
H23C | 0.815183 | 0.983355 | 0.728865 | 0.032* | |
Cl1 | 0.27587 (8) | 0.70192 (9) | 0.57406 (3) | 0.03720 (15) | |
Cl2 | 0.04931 (9) | 0.71889 (11) | 0.47552 (3) | 0.04679 (18) | |
C24 | 0.0769 (3) | 0.7172 (4) | 0.55546 (13) | 0.0365 (6) | |
H24A | 0.047093 | 0.815922 | 0.575214 | 0.044* | |
H24B | 0.005871 | 0.626610 | 0.571156 | 0.044* |
U11 | U22 | U33 | U12 | U13 | U23 | |
I1 | 0.01424 (6) | 0.02080 (7) | 0.01537 (6) | 0.00052 (5) | 0.00161 (5) | 0.00211 (5) |
I2 | 0.03007 (8) | 0.01919 (7) | 0.01743 (7) | 0.00196 (6) | 0.00370 (6) | 0.00084 (5) |
I3 | 0.01655 (6) | 0.01388 (6) | 0.02183 (7) | 0.00186 (5) | 0.00191 (5) | 0.00082 (5) |
I4 | 0.03274 (8) | 0.02312 (7) | 0.02366 (8) | −0.00002 (6) | −0.00650 (6) | 0.00070 (6) |
Se1 | 0.01255 (9) | 0.01629 (9) | 0.01856 (10) | −0.00137 (7) | 0.00119 (7) | 0.00550 (8) |
N1 | 0.0109 (7) | 0.0130 (7) | 0.0153 (8) | 0.0003 (6) | 0.0018 (6) | 0.0036 (6) |
N2 | 0.0137 (8) | 0.0168 (8) | 0.0147 (8) | 0.0021 (6) | 0.0011 (6) | 0.0029 (6) |
C1 | 0.0133 (9) | 0.0105 (8) | 0.0154 (9) | −0.0001 (7) | 0.0006 (7) | −0.0002 (7) |
C2 | 0.0141 (9) | 0.0153 (9) | 0.0203 (10) | −0.0008 (7) | 0.0031 (8) | 0.0067 (8) |
C3 | 0.0182 (10) | 0.0271 (11) | 0.0221 (11) | 0.0058 (9) | 0.0064 (8) | 0.0072 (9) |
C4 | 0.0207 (11) | 0.0252 (11) | 0.0239 (11) | 0.0092 (9) | 0.0065 (9) | 0.0052 (9) |
C5 | 0.0148 (10) | 0.0245 (11) | 0.0244 (11) | 0.0071 (8) | 0.0013 (8) | 0.0051 (9) |
C6 | 0.0138 (9) | 0.0150 (9) | 0.0115 (9) | 0.0006 (7) | 0.0013 (7) | 0.0025 (7) |
C7 | 0.0152 (9) | 0.0146 (9) | 0.0110 (9) | 0.0020 (7) | 0.0027 (7) | 0.0021 (7) |
C8 | 0.0150 (9) | 0.0180 (9) | 0.0133 (9) | 0.0049 (7) | 0.0005 (7) | 0.0032 (7) |
C9 | 0.0129 (9) | 0.0237 (10) | 0.0112 (9) | 0.0009 (8) | 0.0028 (7) | 0.0023 (8) |
C10 | 0.0172 (10) | 0.0180 (10) | 0.0167 (10) | −0.0016 (8) | 0.0010 (8) | −0.0023 (8) |
C11 | 0.0188 (10) | 0.0146 (9) | 0.0152 (10) | 0.0009 (8) | 0.0016 (8) | 0.0029 (7) |
C12 | 0.0181 (10) | 0.0140 (9) | 0.0179 (10) | 0.0016 (7) | −0.0002 (8) | 0.0014 (7) |
C13 | 0.0163 (10) | 0.0343 (12) | 0.0139 (10) | 0.0019 (9) | −0.0015 (8) | 0.0013 (9) |
C14 | 0.0299 (12) | 0.0147 (10) | 0.0239 (11) | 0.0034 (9) | −0.0033 (9) | −0.0006 (8) |
C15 | 0.0142 (9) | 0.0175 (9) | 0.0125 (9) | 0.0016 (7) | −0.0015 (7) | 0.0029 (7) |
C16 | 0.0156 (9) | 0.0185 (10) | 0.0184 (10) | 0.0004 (8) | −0.0034 (8) | −0.0014 (8) |
C17 | 0.0216 (11) | 0.0300 (12) | 0.0173 (11) | 0.0031 (9) | −0.0045 (8) | −0.0045 (9) |
C18 | 0.0214 (11) | 0.0350 (13) | 0.0161 (10) | 0.0032 (9) | −0.0026 (8) | 0.0052 (9) |
C19 | 0.0218 (11) | 0.0233 (11) | 0.0195 (11) | 0.0034 (9) | 0.0008 (8) | 0.0083 (8) |
C20 | 0.0139 (9) | 0.0188 (10) | 0.0160 (10) | 0.0029 (7) | −0.0015 (7) | 0.0015 (8) |
C21 | 0.0263 (12) | 0.0178 (10) | 0.0289 (12) | 0.0006 (9) | −0.0035 (10) | −0.0019 (9) |
C22 | 0.0455 (16) | 0.0535 (18) | 0.0165 (12) | 0.0089 (14) | −0.0040 (11) | 0.0094 (11) |
C23 | 0.0262 (11) | 0.0163 (10) | 0.0219 (11) | 0.0039 (8) | 0.0009 (9) | 0.0009 (8) |
Cl1 | 0.0272 (3) | 0.0408 (4) | 0.0424 (4) | 0.0028 (3) | 0.0020 (3) | −0.0040 (3) |
Cl2 | 0.0392 (4) | 0.0684 (5) | 0.0305 (4) | −0.0015 (4) | 0.0049 (3) | 0.0049 (3) |
C24 | 0.0232 (12) | 0.0535 (17) | 0.0302 (14) | −0.0007 (12) | 0.0038 (10) | −0.0056 (12) |
I1—Se1 | 2.5959 (3) | C12—H12B | 0.9800 |
I2—I3 | 3.0098 (2) | C12—H12C | 0.9800 |
I3—I4 | 2.8428 (2) | C13—H13A | 0.9800 |
Se1—C1 | 1.928 (2) | C13—H13B | 0.9800 |
N1—C1 | 1.331 (3) | C13—H13C | 0.9800 |
N1—C2 | 1.488 (3) | C14—H14A | 0.9800 |
N1—C6 | 1.454 (3) | C14—H14B | 0.9800 |
N2—C1 | 1.338 (3) | C14—H14C | 0.9800 |
N2—C5 | 1.506 (3) | C15—C16 | 1.399 (3) |
N2—C15 | 1.453 (3) | C15—C20 | 1.396 (3) |
C2—H2A | 0.9900 | C16—C17 | 1.396 (3) |
C2—H2B | 0.9900 | C16—C21 | 1.505 (3) |
C2—C3 | 1.513 (3) | C17—H17 | 0.9500 |
C3—H3A | 0.9900 | C17—C18 | 1.394 (3) |
C3—H3B | 0.9900 | C18—C19 | 1.391 (3) |
C3—C4 | 1.527 (3) | C18—C22 | 1.506 (3) |
C4—H4A | 0.9900 | C19—H19 | 0.9500 |
C4—H4B | 0.9900 | C19—C20 | 1.393 (3) |
C4—C5 | 1.509 (3) | C20—C23 | 1.507 (3) |
C5—H5A | 0.9900 | C21—H21A | 0.9800 |
C5—H5B | 0.9900 | C21—H21B | 0.9800 |
C6—C7 | 1.402 (3) | C21—H21C | 0.9800 |
C6—C11 | 1.402 (3) | C22—H22A | 0.9800 |
C7—C8 | 1.399 (3) | C22—H22B | 0.9800 |
C7—C12 | 1.508 (3) | C22—H22C | 0.9800 |
C8—H8 | 0.9500 | C23—H23A | 0.9800 |
C8—C9 | 1.389 (3) | C23—H23B | 0.9800 |
C9—C10 | 1.392 (3) | C23—H23C | 0.9800 |
C9—C13 | 1.510 (3) | Cl1—C24 | 1.754 (3) |
C10—H10 | 0.9500 | Cl2—C24 | 1.775 (3) |
C10—C11 | 1.395 (3) | C24—H24A | 0.9900 |
C11—C14 | 1.510 (3) | C24—H24B | 0.9900 |
C12—H12A | 0.9800 | ||
I4—I3—I2 | 178.081 (7) | H12A—C12—H12C | 109.5 |
C1—Se1—I1 | 100.02 (6) | H12B—C12—H12C | 109.5 |
C1—N1—C2 | 120.48 (17) | C9—C13—H13A | 109.5 |
C1—N1—C6 | 122.97 (17) | C9—C13—H13B | 109.5 |
C6—N1—C2 | 116.54 (16) | C9—C13—H13C | 109.5 |
C1—N2—C5 | 126.83 (18) | H13A—C13—H13B | 109.5 |
C1—N2—C15 | 121.19 (17) | H13A—C13—H13C | 109.5 |
C15—N2—C5 | 111.95 (16) | H13B—C13—H13C | 109.5 |
N1—C1—Se1 | 120.79 (14) | C11—C14—H14A | 109.5 |
N1—C1—N2 | 123.24 (18) | C11—C14—H14B | 109.5 |
N2—C1—Se1 | 115.96 (15) | C11—C14—H14C | 109.5 |
N1—C2—H2A | 109.0 | H14A—C14—H14B | 109.5 |
N1—C2—H2B | 109.0 | H14A—C14—H14C | 109.5 |
N1—C2—C3 | 112.86 (17) | H14B—C14—H14C | 109.5 |
H2A—C2—H2B | 107.8 | C16—C15—N2 | 118.03 (18) |
C3—C2—H2A | 109.0 | C20—C15—N2 | 118.86 (18) |
C3—C2—H2B | 109.0 | C20—C15—C16 | 122.89 (19) |
C2—C3—H3A | 109.3 | C15—C16—C21 | 122.1 (2) |
C2—C3—H3B | 109.3 | C17—C16—C15 | 117.1 (2) |
C2—C3—C4 | 111.52 (18) | C17—C16—C21 | 120.8 (2) |
H3A—C3—H3B | 108.0 | C16—C17—H17 | 119.1 |
C4—C3—H3A | 109.3 | C18—C17—C16 | 121.9 (2) |
C4—C3—H3B | 109.3 | C18—C17—H17 | 119.1 |
C3—C4—H4A | 108.8 | C17—C18—C22 | 121.1 (2) |
C3—C4—H4B | 108.8 | C19—C18—C17 | 118.8 (2) |
H4A—C4—H4B | 107.7 | C19—C18—C22 | 120.0 (2) |
C5—C4—C3 | 113.74 (19) | C18—C19—H19 | 119.2 |
C5—C4—H4A | 108.8 | C18—C19—C20 | 121.6 (2) |
C5—C4—H4B | 108.8 | C20—C19—H19 | 119.2 |
N2—C5—C4 | 115.55 (18) | C15—C20—C23 | 121.82 (19) |
N2—C5—H5A | 108.4 | C19—C20—C15 | 117.6 (2) |
N2—C5—H5B | 108.4 | C19—C20—C23 | 120.6 (2) |
C4—C5—H5A | 108.4 | C16—C21—H21A | 109.5 |
C4—C5—H5B | 108.4 | C16—C21—H21B | 109.5 |
H5A—C5—H5B | 107.5 | C16—C21—H21C | 109.5 |
C7—C6—N1 | 118.44 (17) | H21A—C21—H21B | 109.5 |
C11—C6—N1 | 119.68 (17) | H21A—C21—H21C | 109.5 |
C11—C6—C7 | 121.64 (18) | H21B—C21—H21C | 109.5 |
C6—C7—C12 | 123.53 (18) | C18—C22—H22A | 109.5 |
C8—C7—C6 | 117.94 (18) | C18—C22—H22B | 109.5 |
C8—C7—C12 | 118.52 (18) | C18—C22—H22C | 109.5 |
C7—C8—H8 | 119.0 | H22A—C22—H22B | 109.5 |
C9—C8—C7 | 122.01 (19) | H22A—C22—H22C | 109.5 |
C9—C8—H8 | 119.0 | H22B—C22—H22C | 109.5 |
C8—C9—C10 | 118.34 (19) | C20—C23—H23A | 109.5 |
C8—C9—C13 | 120.82 (19) | C20—C23—H23B | 109.5 |
C10—C9—C13 | 120.80 (19) | C20—C23—H23C | 109.5 |
C9—C10—H10 | 118.9 | H23A—C23—H23B | 109.5 |
C9—C10—C11 | 122.14 (19) | H23A—C23—H23C | 109.5 |
C11—C10—H10 | 118.9 | H23B—C23—H23C | 109.5 |
C6—C11—C14 | 123.29 (19) | Cl1—C24—Cl2 | 111.17 (15) |
C10—C11—C6 | 117.91 (19) | Cl1—C24—H24A | 109.4 |
C10—C11—C14 | 118.75 (19) | Cl1—C24—H24B | 109.4 |
C7—C12—H12A | 109.5 | Cl2—C24—H24A | 109.4 |
C7—C12—H12B | 109.5 | Cl2—C24—H24B | 109.4 |
C7—C12—H12C | 109.5 | H24A—C24—H24B | 108.0 |
H12A—C12—H12B | 109.5 | ||
N1—C2—C3—C4 | 52.9 (3) | C6—C7—C8—C9 | 0.3 (3) |
N1—C6—C7—C8 | −175.98 (18) | C7—C6—C11—C10 | 2.2 (3) |
N1—C6—C7—C12 | 2.7 (3) | C7—C6—C11—C14 | −175.1 (2) |
N1—C6—C11—C10 | 176.54 (18) | C7—C8—C9—C10 | 0.3 (3) |
N1—C6—C11—C14 | −0.7 (3) | C7—C8—C9—C13 | 177.99 (19) |
N2—C15—C16—C17 | 174.89 (19) | C8—C9—C10—C11 | 0.4 (3) |
N2—C15—C16—C21 | −5.0 (3) | C9—C10—C11—C6 | −1.6 (3) |
N2—C15—C20—C19 | −174.33 (18) | C9—C10—C11—C14 | 175.8 (2) |
N2—C15—C20—C23 | 6.8 (3) | C11—C6—C7—C8 | −1.5 (3) |
C1—N1—C2—C3 | −82.9 (2) | C11—C6—C7—C12 | 177.10 (19) |
C1—N1—C6—C7 | −118.8 (2) | C12—C7—C8—C9 | −178.42 (19) |
C1—N1—C6—C11 | 66.7 (3) | C13—C9—C10—C11 | −177.3 (2) |
C1—N2—C5—C4 | 27.3 (3) | C15—N2—C1—Se1 | 20.8 (2) |
C1—N2—C15—C16 | 84.3 (2) | C15—N2—C1—N1 | −160.43 (19) |
C1—N2—C15—C20 | −100.9 (2) | C15—N2—C5—C4 | −154.56 (18) |
C2—N1—C1—Se1 | −162.61 (14) | C15—C16—C17—C18 | −1.5 (3) |
C2—N1—C1—N2 | 18.7 (3) | C16—C15—C20—C19 | 0.2 (3) |
C2—N1—C6—C7 | 62.0 (2) | C16—C15—C20—C23 | −178.7 (2) |
C2—N1—C6—C11 | −112.6 (2) | C16—C17—C18—C19 | 2.0 (4) |
C2—C3—C4—C5 | 31.2 (3) | C16—C17—C18—C22 | −175.8 (2) |
C3—C4—C5—N2 | −75.4 (3) | C17—C18—C19—C20 | −1.4 (4) |
C5—N2—C1—Se1 | −161.26 (16) | C18—C19—C20—C15 | 0.4 (3) |
C5—N2—C1—N1 | 17.5 (3) | C18—C19—C20—C23 | 179.3 (2) |
C5—N2—C15—C16 | −93.9 (2) | C20—C15—C16—C17 | 0.3 (3) |
C5—N2—C15—C20 | 80.8 (2) | C20—C15—C16—C21 | −179.6 (2) |
C6—N1—C1—Se1 | 18.2 (3) | C21—C16—C17—C18 | 178.5 (2) |
C6—N1—C1—N2 | −160.53 (19) | C22—C18—C19—C20 | 176.4 (2) |
C6—N1—C2—C3 | 96.3 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2B···I3i | 0.99 | 3.24 | 3.755 (2) | 114 |
C4—H4A···I3ii | 0.99 | 3.15 | 3.748 (2) | 120 |
C5—H5A···I1i | 0.99 | 3.09 | 3.930 (2) | 144 |
Symmetry codes: (i) x−1, y, z; (ii) x−1, y+1, z. |
3.333(I1.5)·C26H35N2OSe | F(000) = 4096 |
Mr = 1105.02 | Dx = 2.214 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 13.2501 (6) Å | Cell parameters from 9214 reflections |
b = 11.0708 (6) Å | θ = 2.4–26.1° |
c = 45.509 (3) Å | µ = 5.81 mm−1 |
β = 96.722 (2)° | T = 100 K |
V = 6629.7 (6) Å3 | Plate, red |
Z = 8 | 0.17 × 0.15 × 0.05 mm |
Bruker D8 Venture Photon 2 diffractometer | 5737 reflections with I > 2σ(I) |
Radiation source: Incoatec IµS | Rint = 0.041 |
φ and ω scans | θmax = 26.2°, θmin = 2.4° |
Absorption correction: multi-scan SADABS v2016/2 (Bruker AXS Inc., 2017) | h = −16→15 |
Tmin = 0.561, Tmax = 0.745 | k = −13→13 |
46614 measured reflections | l = −56→56 |
6580 independent reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.067 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.142 | H-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 parameters | Δρmax = 4.07 e Å−3 |
0 restraints | Δρmin = −3.13 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
I1 | 0.500000 | 0.500000 | 0.500000 | 0.0499 (3) | |
I2 | 0.59217 (7) | 0.28252 (10) | 0.48034 (2) | 0.0629 (3) | |
I3 | 0.43289 (6) | 0.24158 (7) | 0.42050 (2) | 0.0447 (2) | |
I4 | 0.30499 (7) | 0.20343 (7) | 0.36906 (2) | 0.0472 (2) | |
I5 | 0.14036 (7) | 0.19618 (11) | 0.30440 (2) | 0.0644 (3) | |
I6 | 0.000000 | 0.19062 (9) | 0.250000 | 0.0399 (3) | |
Se1 | 0.43060 (8) | 0.85323 (11) | 0.36915 (2) | 0.0365 (3) | |
O1 | 0.5273 (8) | 1.0240 (10) | 0.33671 (19) | 0.073 (4) | |
N1 | 0.2752 (7) | 0.6675 (9) | 0.36531 (18) | 0.044 (3) | |
N2 | 0.3725 (5) | 0.7013 (6) | 0.41039 (15) | 0.0162 (14) | |
C1 | 0.3465 (6) | 0.7280 (8) | 0.38187 (19) | 0.0193 (17) | |
C2 | 0.3169 (8) | 0.6205 (10) | 0.4295 (2) | 0.034 (2) | |
H2A | 0.331984 | 0.646455 | 0.450415 | 0.041* | |
H2B | 0.341989 | 0.536748 | 0.428052 | 0.041* | |
C3 | 0.2019 (10) | 0.6222 (13) | 0.4209 (3) | 0.053 (3) | |
H3A | 0.179667 | 0.705221 | 0.415208 | 0.063* | |
H3B | 0.167092 | 0.597485 | 0.438038 | 0.063* | |
C4 | 0.1723 (7) | 0.5353 (9) | 0.3947 (2) | 0.028 (2) | |
H4A | 0.164383 | 0.452561 | 0.402371 | 0.033* | |
H4B | 0.106332 | 0.560557 | 0.384022 | 0.033* | |
C5 | 0.2511 (10) | 0.5353 (10) | 0.3741 (3) | 0.041 (3) | |
H5A | 0.226572 | 0.488629 | 0.356082 | 0.050* | |
H5B | 0.313692 | 0.496215 | 0.383618 | 0.050* | |
C6 | 0.4604 (6) | 0.7580 (8) | 0.42725 (18) | 0.0182 (17) | |
C7 | 0.4461 (7) | 0.8626 (8) | 0.44333 (18) | 0.0201 (18) | |
C8 | 0.5304 (7) | 0.9104 (9) | 0.46074 (19) | 0.026 (2) | |
H8 | 0.522867 | 0.982926 | 0.471410 | 0.031* | |
C9 | 0.6241 (7) | 0.8553 (9) | 0.46289 (19) | 0.025 (2) | |
C10 | 0.6357 (7) | 0.7511 (9) | 0.44608 (19) | 0.0232 (19) | |
H10 | 0.700970 | 0.715002 | 0.446795 | 0.028* | |
C11 | 0.5552 (7) | 0.6996 (8) | 0.4285 (2) | 0.0220 (18) | |
C12 | 0.3427 (8) | 0.9228 (9) | 0.4419 (2) | 0.033 (2) | |
H12A | 0.315041 | 0.934670 | 0.421196 | 0.049* | |
H12B | 0.349752 | 1.001268 | 0.451932 | 0.049* | |
H12C | 0.296589 | 0.871426 | 0.451735 | 0.049* | |
C13 | 0.7122 (8) | 0.9065 (10) | 0.4830 (2) | 0.036 (2) | |
H13A | 0.710490 | 0.875263 | 0.503125 | 0.054* | |
H13B | 0.707292 | 0.994812 | 0.483268 | 0.054* | |
H13C | 0.776202 | 0.882702 | 0.475830 | 0.054* | |
C14 | 0.5692 (8) | 0.5867 (9) | 0.4110 (2) | 0.031 (2) | |
H14A | 0.523956 | 0.523247 | 0.416864 | 0.047* | |
H14B | 0.639883 | 0.559504 | 0.414886 | 0.047* | |
H14C | 0.552801 | 0.603754 | 0.389857 | 0.047* | |
C15 | 0.2352 (7) | 0.7035 (10) | 0.3357 (2) | 0.029 (2) | |
C16 | 0.1632 (7) | 0.7955 (11) | 0.3313 (2) | 0.032 (2) | |
C17 | 0.1323 (7) | 0.8316 (10) | 0.3026 (2) | 0.030 (2) | |
H17 | 0.085051 | 0.896115 | 0.299273 | 0.036* | |
C18 | 0.1684 (7) | 0.7761 (8) | 0.27840 (19) | 0.0214 (18) | |
C19 | 0.2352 (7) | 0.6804 (8) | 0.2838 (2) | 0.0231 (19) | |
H19 | 0.257980 | 0.639172 | 0.267535 | 0.028* | |
C20 | 0.2703 (7) | 0.6424 (8) | 0.3125 (2) | 0.027 (2) | |
C21 | 0.1246 (9) | 0.8563 (15) | 0.3571 (3) | 0.059 (4) | |
H21A | 0.180705 | 0.898396 | 0.368784 | 0.088* | |
H21B | 0.095920 | 0.795797 | 0.369449 | 0.088* | |
H21C | 0.071839 | 0.914792 | 0.349916 | 0.088* | |
C22 | 0.1392 (9) | 0.8227 (10) | 0.2475 (2) | 0.037 (2) | |
H22A | 0.080959 | 0.776817 | 0.238038 | 0.055* | |
H22B | 0.196765 | 0.813270 | 0.235929 | 0.055* | |
H22C | 0.121055 | 0.908338 | 0.248265 | 0.055* | |
C23 | 0.3506 (10) | 0.5428 (10) | 0.3162 (3) | 0.044 (3) | |
H23A | 0.319665 | 0.467816 | 0.322295 | 0.066* | |
H23B | 0.405642 | 0.566869 | 0.331384 | 0.066* | |
H23C | 0.378158 | 0.529814 | 0.297399 | 0.066* | |
C24 | 0.3949 (8) | 0.8837 (9) | 0.3274 (2) | 0.029 (2) | |
H24A | 0.403421 | 0.809457 | 0.315766 | 0.035* | |
H24B | 0.323303 | 0.910506 | 0.323420 | 0.035* | |
C25 | 0.4656 (7) | 0.9816 (9) | 0.3190 (2) | 0.027 (2) | |
C26 | 0.4475 (10) | 1.0260 (11) | 0.2879 (2) | 0.045 (3) | |
H26A | 0.382220 | 1.068489 | 0.284851 | 0.068* | |
H26B | 0.446176 | 0.957286 | 0.274273 | 0.068* | |
H26C | 0.502186 | 1.081401 | 0.284099 | 0.068* |
U11 | U22 | U33 | U12 | U13 | U23 | |
I1 | 0.0343 (5) | 0.0785 (8) | 0.0324 (5) | −0.0317 (6) | −0.0153 (4) | 0.0298 (5) |
I2 | 0.0543 (5) | 0.0807 (7) | 0.0518 (5) | −0.0249 (5) | −0.0017 (4) | 0.0244 (5) |
I3 | 0.0446 (4) | 0.0407 (4) | 0.0521 (5) | −0.0099 (3) | 0.0192 (4) | 0.0084 (3) |
I4 | 0.0676 (5) | 0.0244 (4) | 0.0506 (5) | −0.0038 (4) | 0.0108 (4) | −0.0003 (3) |
I5 | 0.0545 (5) | 0.0851 (7) | 0.0531 (5) | 0.0014 (5) | 0.0039 (4) | 0.0054 (5) |
I6 | 0.0437 (6) | 0.0291 (5) | 0.0498 (6) | 0.000 | 0.0178 (5) | 0.000 |
Se1 | 0.0389 (6) | 0.0451 (6) | 0.0225 (5) | −0.0279 (5) | −0.0089 (4) | 0.0138 (4) |
O1 | 0.079 (7) | 0.092 (8) | 0.042 (5) | −0.069 (6) | −0.022 (5) | 0.028 (5) |
N1 | 0.049 (6) | 0.058 (6) | 0.021 (4) | −0.043 (5) | −0.015 (4) | 0.017 (4) |
N2 | 0.015 (3) | 0.017 (3) | 0.015 (3) | −0.008 (3) | −0.003 (3) | 0.001 (3) |
C1 | 0.021 (4) | 0.020 (4) | 0.016 (4) | −0.001 (4) | 0.001 (3) | −0.001 (3) |
C2 | 0.036 (6) | 0.043 (6) | 0.021 (5) | −0.019 (5) | −0.008 (4) | 0.012 (4) |
C3 | 0.055 (8) | 0.061 (9) | 0.043 (7) | −0.022 (7) | 0.009 (6) | 0.002 (6) |
C4 | 0.028 (5) | 0.030 (5) | 0.026 (5) | −0.012 (4) | 0.004 (4) | 0.002 (4) |
C5 | 0.055 (7) | 0.028 (6) | 0.039 (6) | −0.008 (5) | 0.000 (5) | −0.002 (5) |
C6 | 0.015 (4) | 0.021 (4) | 0.017 (4) | −0.007 (3) | −0.006 (3) | 0.002 (3) |
C7 | 0.023 (4) | 0.022 (4) | 0.015 (4) | −0.002 (4) | 0.004 (3) | −0.002 (3) |
C8 | 0.034 (5) | 0.031 (5) | 0.012 (4) | −0.017 (4) | 0.004 (4) | −0.002 (4) |
C9 | 0.030 (5) | 0.031 (5) | 0.012 (4) | −0.012 (4) | −0.004 (3) | 0.005 (4) |
C10 | 0.019 (4) | 0.029 (5) | 0.021 (4) | −0.003 (4) | −0.003 (3) | 0.006 (4) |
C11 | 0.023 (4) | 0.022 (4) | 0.022 (4) | −0.004 (4) | 0.003 (4) | 0.007 (4) |
C12 | 0.031 (5) | 0.024 (5) | 0.045 (6) | −0.003 (4) | 0.010 (5) | −0.008 (4) |
C13 | 0.040 (6) | 0.035 (6) | 0.031 (5) | −0.016 (5) | −0.008 (5) | −0.002 (5) |
C14 | 0.027 (5) | 0.026 (5) | 0.039 (6) | −0.002 (4) | 0.001 (4) | −0.002 (4) |
C15 | 0.029 (5) | 0.041 (6) | 0.015 (4) | −0.019 (5) | −0.004 (4) | 0.008 (4) |
C16 | 0.026 (5) | 0.050 (7) | 0.022 (5) | −0.019 (5) | 0.008 (4) | −0.010 (5) |
C17 | 0.023 (5) | 0.032 (5) | 0.035 (5) | −0.004 (4) | −0.001 (4) | −0.004 (4) |
C18 | 0.025 (5) | 0.021 (5) | 0.018 (4) | −0.007 (4) | 0.004 (3) | 0.001 (3) |
C19 | 0.025 (5) | 0.022 (5) | 0.021 (4) | −0.005 (4) | −0.004 (4) | −0.002 (4) |
C20 | 0.029 (5) | 0.019 (5) | 0.030 (5) | −0.010 (4) | −0.009 (4) | 0.005 (4) |
C21 | 0.034 (6) | 0.102 (12) | 0.041 (7) | −0.010 (7) | 0.008 (5) | −0.031 (7) |
C22 | 0.047 (6) | 0.041 (6) | 0.019 (5) | −0.003 (5) | −0.007 (4) | 0.010 (4) |
C23 | 0.059 (8) | 0.024 (5) | 0.045 (7) | 0.002 (5) | −0.017 (6) | 0.002 (5) |
C24 | 0.034 (5) | 0.034 (5) | 0.017 (4) | −0.017 (4) | −0.007 (4) | 0.007 (4) |
C25 | 0.026 (5) | 0.029 (5) | 0.027 (5) | −0.012 (4) | 0.004 (4) | 0.002 (4) |
C26 | 0.065 (8) | 0.041 (7) | 0.029 (6) | −0.022 (6) | 0.002 (5) | 0.009 (5) |
I1—I2i | 2.8887 (12) | C12—H12B | 0.9800 |
I1—I2 | 2.8887 (12) | C12—H12C | 0.9800 |
I3—I4 | 2.7570 (13) | C13—H13A | 0.9800 |
I5—I6 | 2.9180 (10) | C13—H13B | 0.9800 |
Se1—C1 | 1.911 (9) | C13—H13C | 0.9800 |
Se1—C24 | 1.935 (9) | C14—H14A | 0.9800 |
O1—C25 | 1.177 (12) | C14—H14B | 0.9800 |
N1—C1 | 1.319 (12) | C14—H14C | 0.9800 |
N1—C5 | 1.560 (14) | C15—C16 | 1.393 (16) |
N1—C15 | 1.446 (12) | C15—C20 | 1.381 (15) |
N2—C1 | 1.337 (11) | C16—C17 | 1.383 (14) |
N2—C2 | 1.501 (11) | C16—C21 | 1.492 (15) |
N2—C6 | 1.459 (10) | C17—H17 | 0.9500 |
C2—H2A | 0.9900 | C17—C18 | 1.395 (13) |
C2—H2B | 0.9900 | C18—C19 | 1.384 (13) |
C2—C3 | 1.529 (16) | C18—C22 | 1.507 (12) |
C3—H3A | 0.9900 | C19—H19 | 0.9500 |
C3—H3B | 0.9900 | C19—C20 | 1.396 (13) |
C3—C4 | 1.545 (16) | C20—C23 | 1.528 (15) |
C4—H4A | 0.9900 | C21—H21A | 0.9800 |
C4—H4B | 0.9900 | C21—H21B | 0.9800 |
C4—C5 | 1.485 (15) | C21—H21C | 0.9800 |
C5—H5A | 0.9900 | C22—H22A | 0.9800 |
C5—H5B | 0.9900 | C22—H22B | 0.9800 |
C6—C7 | 1.395 (12) | C22—H22C | 0.9800 |
C6—C11 | 1.408 (13) | C23—H23A | 0.9800 |
C7—C8 | 1.396 (12) | C23—H23B | 0.9800 |
C7—C12 | 1.518 (13) | C23—H23C | 0.9800 |
C8—H8 | 0.9500 | C24—H24A | 0.9900 |
C8—C9 | 1.377 (14) | C24—H24B | 0.9900 |
C9—C10 | 1.402 (14) | C24—C25 | 1.510 (12) |
C9—C13 | 1.508 (13) | C25—C26 | 1.492 (14) |
C10—H10 | 0.9500 | C26—H26A | 0.9800 |
C10—C11 | 1.379 (13) | C26—H26B | 0.9800 |
C11—C14 | 1.507 (13) | C26—H26C | 0.9800 |
C12—H12A | 0.9800 | ||
I2i—I1—I2 | 180.00 (4) | C9—C13—H13C | 109.5 |
I5ii—I6—I5 | 177.58 (6) | H13A—C13—H13B | 109.5 |
C1—Se1—C24 | 109.9 (4) | H13A—C13—H13C | 109.5 |
C1—N1—C5 | 119.0 (8) | H13B—C13—H13C | 109.5 |
C1—N1—C15 | 123.6 (8) | C11—C14—H14A | 109.5 |
C15—N1—C5 | 115.6 (8) | C11—C14—H14B | 109.5 |
C1—N2—C2 | 127.4 (7) | C11—C14—H14C | 109.5 |
C1—N2—C6 | 121.0 (7) | H14A—C14—H14B | 109.5 |
C6—N2—C2 | 111.5 (7) | H14A—C14—H14C | 109.5 |
N1—C1—Se1 | 126.8 (7) | H14B—C14—H14C | 109.5 |
N1—C1—N2 | 121.9 (8) | C16—C15—N1 | 120.2 (10) |
N2—C1—Se1 | 111.2 (6) | C20—C15—N1 | 117.3 (10) |
N2—C2—H2A | 109.1 | C20—C15—C16 | 122.5 (9) |
N2—C2—H2B | 109.1 | C15—C16—C21 | 120.7 (10) |
N2—C2—C3 | 112.7 (8) | C17—C16—C15 | 117.8 (9) |
H2A—C2—H2B | 107.8 | C17—C16—C21 | 121.4 (11) |
C3—C2—H2A | 109.1 | C16—C17—H17 | 119.0 |
C3—C2—H2B | 109.1 | C16—C17—C18 | 121.9 (10) |
C2—C3—H3A | 109.6 | C18—C17—H17 | 119.0 |
C2—C3—H3B | 109.6 | C17—C18—C22 | 120.9 (9) |
C2—C3—C4 | 110.2 (11) | C19—C18—C17 | 117.9 (9) |
H3A—C3—H3B | 108.1 | C19—C18—C22 | 121.2 (9) |
C4—C3—H3A | 109.6 | C18—C19—H19 | 118.9 |
C4—C3—H3B | 109.6 | C18—C19—C20 | 122.3 (9) |
C3—C4—H4A | 109.5 | C20—C19—H19 | 118.9 |
C3—C4—H4B | 109.5 | C15—C20—C19 | 117.4 (9) |
H4A—C4—H4B | 108.1 | C15—C20—C23 | 124.1 (9) |
C5—C4—C3 | 110.8 (9) | C19—C20—C23 | 118.3 (9) |
C5—C4—H4A | 109.5 | C16—C21—H21A | 109.5 |
C5—C4—H4B | 109.5 | C16—C21—H21B | 109.5 |
N1—C5—H5A | 109.7 | C16—C21—H21C | 109.5 |
N1—C5—H5B | 109.7 | H21A—C21—H21B | 109.5 |
C4—C5—N1 | 110.0 (9) | H21A—C21—H21C | 109.5 |
C4—C5—H5A | 109.7 | H21B—C21—H21C | 109.5 |
C4—C5—H5B | 109.7 | C18—C22—H22A | 109.5 |
H5A—C5—H5B | 108.2 | C18—C22—H22B | 109.5 |
C7—C6—N2 | 119.0 (8) | C18—C22—H22C | 109.5 |
C7—C6—C11 | 122.3 (8) | H22A—C22—H22B | 109.5 |
C11—C6—N2 | 118.5 (8) | H22A—C22—H22C | 109.5 |
C6—C7—C8 | 117.6 (8) | H22B—C22—H22C | 109.5 |
C6—C7—C12 | 121.3 (8) | C20—C23—H23A | 109.5 |
C8—C7—C12 | 121.1 (8) | C20—C23—H23B | 109.5 |
C7—C8—H8 | 119.1 | C20—C23—H23C | 109.5 |
C9—C8—C7 | 121.9 (9) | H23A—C23—H23B | 109.5 |
C9—C8—H8 | 119.1 | H23A—C23—H23C | 109.5 |
C8—C9—C10 | 118.7 (8) | H23B—C23—H23C | 109.5 |
C8—C9—C13 | 120.3 (9) | Se1—C24—H24A | 110.4 |
C10—C9—C13 | 121.0 (9) | Se1—C24—H24B | 110.4 |
C9—C10—H10 | 119.0 | H24A—C24—H24B | 108.6 |
C11—C10—C9 | 122.0 (9) | C25—C24—Se1 | 106.5 (6) |
C11—C10—H10 | 119.0 | C25—C24—H24A | 110.4 |
C6—C11—C14 | 121.6 (8) | C25—C24—H24B | 110.4 |
C10—C11—C6 | 117.4 (9) | O1—C25—C24 | 121.2 (9) |
C10—C11—C14 | 121.0 (9) | O1—C25—C26 | 122.6 (9) |
C7—C12—H12A | 109.5 | C26—C25—C24 | 116.1 (8) |
C7—C12—H12B | 109.5 | C25—C26—H26A | 109.5 |
C7—C12—H12C | 109.5 | C25—C26—H26B | 109.5 |
H12A—C12—H12B | 109.5 | C25—C26—H26C | 109.5 |
H12A—C12—H12C | 109.5 | H26A—C26—H26B | 109.5 |
H12B—C12—H12C | 109.5 | H26A—C26—H26C | 109.5 |
C9—C13—H13A | 109.5 | H26B—C26—H26C | 109.5 |
C9—C13—H13B | 109.5 | ||
Se1—C24—C25—O1 | −0.2 (14) | C6—N2—C2—C3 | 144.5 (9) |
Se1—C24—C25—C26 | −176.1 (8) | C6—C7—C8—C9 | −1.9 (13) |
N1—C15—C16—C17 | 175.9 (9) | C7—C6—C11—C10 | −1.3 (13) |
N1—C15—C16—C21 | −1.3 (15) | C7—C6—C11—C14 | −180.0 (8) |
N1—C15—C20—C19 | −177.2 (8) | C7—C8—C9—C10 | 2.7 (13) |
N1—C15—C20—C23 | −2.0 (14) | C7—C8—C9—C13 | −177.1 (9) |
N2—C2—C3—C4 | 82.5 (12) | C8—C9—C10—C11 | −2.9 (13) |
N2—C6—C7—C8 | 176.0 (8) | C9—C10—C11—C6 | 2.1 (13) |
N2—C6—C7—C12 | −4.2 (13) | C9—C10—C11—C14 | −179.1 (8) |
N2—C6—C11—C10 | −176.1 (8) | C11—C6—C7—C8 | 1.2 (13) |
N2—C6—C11—C14 | 5.2 (12) | C11—C6—C7—C12 | −179.0 (9) |
C1—N1—C5—C4 | 88.7 (13) | C12—C7—C8—C9 | 178.3 (9) |
C1—N1—C15—C16 | −79.1 (14) | C13—C9—C10—C11 | 177.0 (9) |
C1—N1—C15—C20 | 101.6 (13) | C15—N1—C1—Se1 | −13.0 (17) |
C1—N2—C2—C3 | −31.8 (15) | C15—N1—C1—N2 | 171.2 (10) |
C1—N2—C6—C7 | 93.2 (10) | C15—N1—C5—C4 | −106.0 (11) |
C1—N2—C6—C11 | −91.8 (10) | C15—C16—C17—C18 | 2.2 (14) |
C2—N2—C1—Se1 | 171.3 (8) | C16—C15—C20—C19 | 3.5 (14) |
C2—N2—C1—N1 | −12.4 (15) | C16—C15—C20—C23 | 178.8 (10) |
C2—N2—C6—C7 | −83.4 (10) | C16—C17—C18—C19 | 1.5 (14) |
C2—N2—C6—C11 | 91.6 (10) | C16—C17—C18—C22 | −175.7 (9) |
C2—C3—C4—C5 | −35.6 (13) | C17—C18—C19—C20 | −2.9 (14) |
C3—C4—C5—N1 | −51.3 (12) | C18—C19—C20—C15 | 0.5 (14) |
C5—N1—C1—Se1 | 151.0 (8) | C18—C19—C20—C23 | −175.0 (9) |
C5—N1—C1—N2 | −24.8 (15) | C20—C15—C16—C17 | −4.9 (14) |
C5—N1—C15—C16 | 116.4 (11) | C20—C15—C16—C21 | 177.9 (10) |
C5—N1—C15—C20 | −62.9 (12) | C21—C16—C17—C18 | 179.5 (10) |
C6—N2—C1—Se1 | −4.7 (10) | C22—C18—C19—C20 | 174.2 (9) |
C6—N2—C1—N1 | 171.7 (9) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, y, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2A···I2i | 0.99 | 3.29 | 4.274 (10) | 173 |
C3—H3B···I2iii | 0.99 | 3.06 | 3.674 (14) | 122 |
C4—H4B···O1iv | 0.99 | 2.32 | 3.081 (13) | 133 |
C26—H26B···I6v | 0.98 | 3.26 | 4.186 (13) | 158 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (iii) x−1/2, y+1/2, z; (iv) x−1/2, y−1/2, z; (v) x+1/2, y+1/2, z. |
I3·C29H41N2OS | Z = 2 |
Mr = 846.40 | F(000) = 824 |
Triclinic, P1 | Dx = 1.726 Mg m−3 |
a = 8.7838 (8) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 14.2194 (15) Å | Cell parameters from 9680 reflections |
c = 15.1418 (15) Å | θ = 2.6–29.2° |
α = 63.522 (3)° | µ = 2.97 mm−1 |
β = 74.494 (4)° | T = 100 K |
γ = 80.494 (4)° | Block, red |
V = 1628.9 (3) Å3 | 0.11 × 0.09 × 0.08 mm |
Bruker D8 Venture Photon 2 diffractometer | 6624 reflections with I > 2σ(I) |
Radiation source: Incoatec IµS | Rint = 0.052 |
φ and ω scans | θmax = 29.2°, θmin = 2.4° |
Absorption correction: multi-scan SADABS v2016/2 (Bruker AXS Inc., 2017) | h = −12→12 |
Tmin = 0.645, Tmax = 0.746 | k = −19→19 |
60178 measured reflections | l = −20→20 |
8827 independent reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.033 | H-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 reflections | Δρmax = 2.75 e Å−3 |
333 parameters | Δρmin = −0.92 e Å−3 |
0 restraints |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
I1 | 0.88921 (3) | 0.38632 (2) | 0.09024 (2) | 0.02408 (6) | |
I2 | 0.72699 (3) | 0.19081 (2) | 0.17581 (2) | 0.01934 (5) | |
I3 | 0.56631 (3) | −0.00606 (2) | 0.26107 (2) | 0.03233 (7) | |
S1 | 0.05667 (10) | 0.46475 (7) | 0.36526 (6) | 0.01818 (17) | |
O1 | −0.2113 (3) | 0.5914 (2) | 0.3362 (2) | 0.0295 (6) | |
N1 | 0.2562 (3) | 0.3008 (2) | 0.4062 (2) | 0.0158 (5) | |
N2 | 0.3781 (3) | 0.4598 (2) | 0.2983 (2) | 0.0151 (5) | |
C1 | 0.2498 (4) | 0.4050 (3) | 0.3507 (2) | 0.0160 (6) | |
C2 | 0.5358 (4) | 0.4062 (3) | 0.2800 (3) | 0.0187 (7) | |
H2A | 0.606210 | 0.456891 | 0.220838 | 0.022* | |
H2B | 0.523951 | 0.348077 | 0.263697 | 0.022* | |
C3 | 0.6117 (4) | 0.3626 (3) | 0.3700 (3) | 0.0200 (7) | |
H3A | 0.641039 | 0.421462 | 0.379077 | 0.024* | |
H3B | 0.709748 | 0.320643 | 0.357020 | 0.024* | |
C4 | 0.5003 (4) | 0.2931 (3) | 0.4671 (3) | 0.0202 (7) | |
H4A | 0.563987 | 0.241732 | 0.514877 | 0.024* | |
H4B | 0.433992 | 0.337620 | 0.499304 | 0.024* | |
C5 | 0.3934 (4) | 0.2340 (3) | 0.4472 (3) | 0.0178 (7) | |
H5A | 0.456766 | 0.206050 | 0.398427 | 0.021* | |
H5B | 0.353008 | 0.173277 | 0.511080 | 0.021* | |
C6 | 0.3726 (4) | 0.5737 (3) | 0.2502 (2) | 0.0151 (6) | |
C7 | 0.3515 (4) | 0.6310 (3) | 0.3078 (2) | 0.0153 (6) | |
C8 | 0.3463 (4) | 0.7401 (3) | 0.2572 (3) | 0.0195 (7) | |
H8 | 0.332101 | 0.780318 | 0.295049 | 0.023* | |
C9 | 0.3611 (4) | 0.7927 (3) | 0.1525 (3) | 0.0192 (7) | |
C10 | 0.3879 (4) | 0.7326 (3) | 0.0981 (3) | 0.0202 (7) | |
H10 | 0.401750 | 0.767318 | 0.026604 | 0.024* | |
C11 | 0.3952 (4) | 0.6237 (3) | 0.1443 (2) | 0.0170 (6) | |
C12 | 0.3351 (4) | 0.5792 (3) | 0.4206 (3) | 0.0224 (7) | |
H12A | 0.258625 | 0.524235 | 0.451106 | 0.034* | |
H12B | 0.298035 | 0.631814 | 0.447862 | 0.034* | |
H12C | 0.438003 | 0.547626 | 0.436287 | 0.034* | |
C13 | 0.3458 (5) | 0.9107 (3) | 0.1011 (3) | 0.0294 (9) | |
H13A | 0.242098 | 0.935408 | 0.129688 | 0.044* | |
H13B | 0.356252 | 0.933494 | 0.028483 | 0.044* | |
H13C | 0.429237 | 0.940171 | 0.111580 | 0.044* | |
C14 | 0.4249 (4) | 0.5623 (3) | 0.0809 (3) | 0.0238 (8) | |
H14A | 0.538434 | 0.544417 | 0.064635 | 0.036* | |
H14B | 0.388198 | 0.605143 | 0.018136 | 0.036* | |
H14C | 0.367288 | 0.497542 | 0.118780 | 0.036* | |
C15 | 0.1242 (4) | 0.2398 (3) | 0.4238 (3) | 0.0171 (7) | |
C16 | 0.0226 (4) | 0.2008 (3) | 0.5195 (3) | 0.0184 (7) | |
C17 | −0.0977 (4) | 0.1388 (3) | 0.5347 (3) | 0.0184 (7) | |
H17 | −0.168882 | 0.111907 | 0.598784 | 0.022* | |
C18 | −0.1165 (4) | 0.1151 (3) | 0.4582 (3) | 0.0200 (7) | |
C19 | −0.0101 (4) | 0.1540 (3) | 0.3647 (3) | 0.0202 (7) | |
H19 | −0.021012 | 0.137411 | 0.312567 | 0.024* | |
C20 | 0.1119 (4) | 0.2167 (3) | 0.3459 (3) | 0.0179 (7) | |
C21 | 0.0412 (4) | 0.2253 (3) | 0.6031 (3) | 0.0242 (8) | |
H21A | −0.046736 | 0.197407 | 0.661588 | 0.036* | |
H21B | 0.040869 | 0.301733 | 0.579334 | 0.036* | |
H21C | 0.141434 | 0.192831 | 0.622710 | 0.036* | |
C22 | −0.2460 (4) | 0.0465 (3) | 0.4764 (3) | 0.0231 (7) | |
H22A | −0.203543 | −0.026327 | 0.494570 | 0.035* | |
H22B | −0.286148 | 0.071610 | 0.414741 | 0.035* | |
H22C | −0.332269 | 0.049727 | 0.531638 | 0.035* | |
C23 | 0.2274 (4) | 0.2545 (3) | 0.2448 (3) | 0.0226 (7) | |
H23A | 0.214982 | 0.331255 | 0.209556 | 0.034* | |
H23B | 0.206492 | 0.222537 | 0.203951 | 0.034* | |
H23C | 0.335589 | 0.234230 | 0.255129 | 0.034* | |
C24 | 0.0261 (4) | 0.5487 (3) | 0.2388 (3) | 0.0241 (8) | |
H24A | 0.107782 | 0.601425 | 0.201279 | 0.029* | |
H24B | 0.031337 | 0.506312 | 0.200911 | 0.029* | |
C25 | −0.1369 (4) | 0.6023 (3) | 0.2527 (3) | 0.0206 (7) | |
C26 | −0.1986 (4) | 0.6679 (3) | 0.1584 (3) | 0.0253 (8) | |
H26A | −0.306725 | 0.696259 | 0.177615 | 0.030* | |
H26B | −0.206246 | 0.621959 | 0.126399 | 0.030* | |
C27 | −0.0964 (4) | 0.7601 (3) | 0.0801 (3) | 0.0228 (7) | |
H27 | 0.009408 | 0.730610 | 0.055934 | 0.027* | |
C28 | −0.1738 (5) | 0.8212 (4) | −0.0097 (3) | 0.0357 (10) | |
H28A | −0.188598 | 0.773501 | −0.037240 | 0.053* | |
H28B | −0.105834 | 0.877263 | −0.062013 | 0.053* | |
H28C | −0.276741 | 0.852152 | 0.012194 | 0.053* | |
C29 | −0.0716 (6) | 0.8313 (4) | 0.1254 (4) | 0.0385 (10) | |
H29A | −0.174440 | 0.859613 | 0.151075 | 0.058* | |
H29B | −0.007244 | 0.889470 | 0.073204 | 0.058* | |
H29C | −0.017272 | 0.790800 | 0.180959 | 0.058* |
U11 | U22 | U33 | U12 | U13 | U23 | |
I1 | 0.02009 (11) | 0.02643 (13) | 0.02587 (12) | −0.00218 (9) | −0.00205 (9) | −0.01254 (10) |
I2 | 0.01807 (10) | 0.02349 (12) | 0.01696 (10) | 0.00023 (8) | −0.00447 (8) | −0.00909 (9) |
I3 | 0.03382 (14) | 0.02925 (14) | 0.03432 (14) | −0.00730 (11) | −0.00552 (11) | −0.01298 (12) |
S1 | 0.0152 (4) | 0.0163 (4) | 0.0195 (4) | 0.0007 (3) | −0.0043 (3) | −0.0048 (3) |
O1 | 0.0204 (13) | 0.0303 (15) | 0.0268 (14) | 0.0029 (11) | −0.0008 (11) | −0.0064 (12) |
N1 | 0.0140 (13) | 0.0140 (13) | 0.0205 (14) | −0.0013 (10) | −0.0065 (11) | −0.0067 (11) |
N2 | 0.0142 (13) | 0.0135 (13) | 0.0182 (13) | −0.0003 (10) | −0.0037 (11) | −0.0073 (11) |
C1 | 0.0185 (16) | 0.0162 (16) | 0.0158 (15) | 0.0021 (12) | −0.0058 (12) | −0.0087 (13) |
C2 | 0.0161 (16) | 0.0189 (17) | 0.0195 (16) | 0.0011 (13) | −0.0021 (13) | −0.0083 (14) |
C3 | 0.0161 (16) | 0.0196 (17) | 0.0238 (17) | −0.0014 (13) | −0.0052 (13) | −0.0081 (14) |
C4 | 0.0198 (17) | 0.0187 (17) | 0.0249 (18) | −0.0005 (13) | −0.0100 (14) | −0.0090 (14) |
C5 | 0.0158 (15) | 0.0145 (16) | 0.0228 (17) | 0.0026 (12) | −0.0095 (13) | −0.0059 (14) |
C6 | 0.0143 (15) | 0.0134 (15) | 0.0170 (15) | −0.0017 (12) | −0.0037 (12) | −0.0054 (13) |
C7 | 0.0130 (14) | 0.0175 (16) | 0.0174 (15) | 0.0005 (12) | −0.0032 (12) | −0.0096 (13) |
C8 | 0.0169 (16) | 0.0200 (17) | 0.0252 (18) | −0.0003 (13) | −0.0048 (13) | −0.0130 (15) |
C9 | 0.0153 (16) | 0.0163 (17) | 0.0224 (17) | −0.0033 (13) | −0.0056 (13) | −0.0033 (14) |
C10 | 0.0194 (16) | 0.0217 (18) | 0.0151 (15) | −0.0058 (13) | −0.0035 (13) | −0.0024 (14) |
C11 | 0.0144 (15) | 0.0200 (17) | 0.0180 (16) | 0.0010 (13) | −0.0060 (12) | −0.0085 (14) |
C12 | 0.0252 (18) | 0.0248 (19) | 0.0189 (17) | −0.0015 (14) | −0.0050 (14) | −0.0106 (15) |
C13 | 0.032 (2) | 0.0183 (19) | 0.031 (2) | −0.0063 (16) | −0.0062 (17) | −0.0036 (16) |
C14 | 0.0276 (19) | 0.027 (2) | 0.0198 (17) | 0.0009 (15) | −0.0077 (15) | −0.0115 (15) |
C15 | 0.0143 (15) | 0.0139 (16) | 0.0228 (17) | 0.0009 (12) | −0.0082 (13) | −0.0057 (13) |
C16 | 0.0173 (16) | 0.0187 (17) | 0.0196 (16) | 0.0004 (13) | −0.0058 (13) | −0.0080 (14) |
C17 | 0.0159 (15) | 0.0163 (16) | 0.0197 (16) | 0.0005 (12) | −0.0049 (13) | −0.0047 (14) |
C18 | 0.0161 (16) | 0.0161 (17) | 0.0288 (18) | 0.0019 (13) | −0.0105 (14) | −0.0082 (14) |
C19 | 0.0205 (17) | 0.0193 (17) | 0.0263 (18) | 0.0011 (13) | −0.0121 (14) | −0.0112 (15) |
C20 | 0.0190 (16) | 0.0145 (16) | 0.0203 (16) | 0.0010 (13) | −0.0074 (13) | −0.0063 (13) |
C21 | 0.0249 (18) | 0.031 (2) | 0.0218 (18) | −0.0037 (15) | −0.0044 (14) | −0.0151 (16) |
C22 | 0.0187 (17) | 0.0194 (18) | 0.032 (2) | −0.0020 (14) | −0.0091 (15) | −0.0090 (16) |
C23 | 0.0207 (17) | 0.0270 (19) | 0.0235 (18) | −0.0049 (14) | −0.0049 (14) | −0.0124 (15) |
C24 | 0.0218 (18) | 0.030 (2) | 0.0185 (17) | 0.0027 (15) | −0.0073 (14) | −0.0087 (15) |
C25 | 0.0160 (16) | 0.0157 (17) | 0.0249 (18) | −0.0036 (13) | −0.0043 (14) | −0.0032 (14) |
C26 | 0.0222 (18) | 0.026 (2) | 0.0281 (19) | 0.0005 (15) | −0.0122 (15) | −0.0087 (16) |
C27 | 0.0249 (18) | 0.0217 (18) | 0.0186 (17) | 0.0018 (14) | −0.0023 (14) | −0.0081 (15) |
C28 | 0.039 (2) | 0.035 (2) | 0.0225 (19) | 0.0111 (19) | −0.0091 (17) | −0.0056 (18) |
C29 | 0.046 (3) | 0.029 (2) | 0.045 (3) | −0.0039 (19) | −0.009 (2) | −0.020 (2) |
I1—I2 | 2.9235 (4) | C14—H14A | 0.9800 |
I2—I3 | 2.9332 (5) | C14—H14B | 0.9800 |
S1—C1 | 1.772 (3) | C14—H14C | 0.9800 |
S1—C24 | 1.814 (4) | C15—C16 | 1.399 (5) |
O1—C25 | 1.212 (4) | C15—C20 | 1.392 (5) |
N1—C1 | 1.339 (4) | C16—C17 | 1.395 (5) |
N1—C5 | 1.496 (4) | C16—C21 | 1.508 (5) |
N1—C15 | 1.458 (4) | C17—H17 | 0.9500 |
N2—C1 | 1.329 (4) | C17—C18 | 1.397 (5) |
N2—C2 | 1.486 (4) | C18—C19 | 1.395 (5) |
N2—C6 | 1.448 (4) | C18—C22 | 1.510 (5) |
C2—H2A | 0.9900 | C19—H19 | 0.9500 |
C2—H2B | 0.9900 | C19—C20 | 1.396 (5) |
C2—C3 | 1.510 (5) | C20—C23 | 1.509 (5) |
C3—H3A | 0.9900 | C21—H21A | 0.9800 |
C3—H3B | 0.9900 | C21—H21B | 0.9800 |
C3—C4 | 1.533 (5) | C21—H21C | 0.9800 |
C4—H4A | 0.9900 | C22—H22A | 0.9800 |
C4—H4B | 0.9900 | C22—H22B | 0.9800 |
C4—C5 | 1.522 (5) | C22—H22C | 0.9800 |
C5—H5A | 0.9900 | C23—H23A | 0.9800 |
C5—H5B | 0.9900 | C23—H23B | 0.9800 |
C6—C7 | 1.399 (4) | C23—H23C | 0.9800 |
C6—C11 | 1.406 (4) | C24—H24A | 0.9900 |
C7—C8 | 1.389 (5) | C24—H24B | 0.9900 |
C7—C12 | 1.503 (5) | C24—C25 | 1.516 (5) |
C8—H8 | 0.9500 | C25—C26 | 1.503 (5) |
C8—C9 | 1.398 (5) | C26—H26A | 0.9900 |
C9—C10 | 1.386 (5) | C26—H26B | 0.9900 |
C9—C13 | 1.502 (5) | C26—C27 | 1.537 (5) |
C10—H10 | 0.9500 | C27—H27 | 1.0000 |
C10—C11 | 1.385 (5) | C27—C28 | 1.520 (5) |
C11—C14 | 1.514 (5) | C27—C29 | 1.521 (5) |
C12—H12A | 0.9800 | C28—H28A | 0.9800 |
C12—H12B | 0.9800 | C28—H28B | 0.9800 |
C12—H12C | 0.9800 | C28—H28C | 0.9800 |
C13—H13A | 0.9800 | C29—H29A | 0.9800 |
C13—H13B | 0.9800 | C29—H29B | 0.9800 |
C13—H13C | 0.9800 | C29—H29C | 0.9800 |
I1—I2—I3 | 179.585 (12) | H14B—C14—H14C | 109.5 |
C1—S1—C24 | 106.62 (16) | C16—C15—N1 | 119.3 (3) |
C1—N1—C5 | 127.1 (3) | C20—C15—N1 | 117.9 (3) |
C1—N1—C15 | 119.5 (3) | C20—C15—C16 | 122.7 (3) |
C15—N1—C5 | 113.2 (3) | C15—C16—C21 | 121.5 (3) |
C1—N2—C2 | 121.0 (3) | C17—C16—C15 | 117.5 (3) |
C1—N2—C6 | 122.9 (3) | C17—C16—C21 | 121.0 (3) |
C6—N2—C2 | 115.9 (3) | C16—C17—H17 | 119.1 |
N1—C1—S1 | 113.6 (2) | C16—C17—C18 | 121.8 (3) |
N2—C1—S1 | 123.0 (3) | C18—C17—H17 | 119.1 |
N2—C1—N1 | 123.0 (3) | C17—C18—C22 | 121.1 (3) |
N2—C2—H2A | 109.1 | C19—C18—C17 | 118.6 (3) |
N2—C2—H2B | 109.1 | C19—C18—C22 | 120.3 (3) |
N2—C2—C3 | 112.6 (3) | C18—C19—H19 | 119.1 |
H2A—C2—H2B | 107.8 | C18—C19—C20 | 121.7 (3) |
C3—C2—H2A | 109.1 | C20—C19—H19 | 119.1 |
C3—C2—H2B | 109.1 | C15—C20—C19 | 117.7 (3) |
C2—C3—H3A | 109.3 | C15—C20—C23 | 122.2 (3) |
C2—C3—H3B | 109.3 | C19—C20—C23 | 120.0 (3) |
C2—C3—C4 | 111.6 (3) | C16—C21—H21A | 109.5 |
H3A—C3—H3B | 108.0 | C16—C21—H21B | 109.5 |
C4—C3—H3A | 109.3 | C16—C21—H21C | 109.5 |
C4—C3—H3B | 109.3 | H21A—C21—H21B | 109.5 |
C3—C4—H4A | 109.1 | H21A—C21—H21C | 109.5 |
C3—C4—H4B | 109.1 | H21B—C21—H21C | 109.5 |
H4A—C4—H4B | 107.9 | C18—C22—H22A | 109.5 |
C5—C4—C3 | 112.3 (3) | C18—C22—H22B | 109.5 |
C5—C4—H4A | 109.1 | C18—C22—H22C | 109.5 |
C5—C4—H4B | 109.1 | H22A—C22—H22B | 109.5 |
N1—C5—C4 | 113.2 (3) | H22A—C22—H22C | 109.5 |
N1—C5—H5A | 108.9 | H22B—C22—H22C | 109.5 |
N1—C5—H5B | 108.9 | C20—C23—H23A | 109.5 |
C4—C5—H5A | 108.9 | C20—C23—H23B | 109.5 |
C4—C5—H5B | 108.9 | C20—C23—H23C | 109.5 |
H5A—C5—H5B | 107.7 | H23A—C23—H23B | 109.5 |
C7—C6—N2 | 120.5 (3) | H23A—C23—H23C | 109.5 |
C7—C6—C11 | 121.6 (3) | H23B—C23—H23C | 109.5 |
C11—C6—N2 | 117.8 (3) | S1—C24—H24A | 110.5 |
C6—C7—C12 | 122.6 (3) | S1—C24—H24B | 110.5 |
C8—C7—C6 | 117.6 (3) | H24A—C24—H24B | 108.7 |
C8—C7—C12 | 119.8 (3) | C25—C24—S1 | 106.0 (2) |
C7—C8—H8 | 118.8 | C25—C24—H24A | 110.5 |
C7—C8—C9 | 122.3 (3) | C25—C24—H24B | 110.5 |
C9—C8—H8 | 118.8 | O1—C25—C24 | 120.5 (3) |
C8—C9—C13 | 120.8 (3) | O1—C25—C26 | 123.0 (3) |
C10—C9—C8 | 118.0 (3) | C26—C25—C24 | 116.5 (3) |
C10—C9—C13 | 121.2 (3) | C25—C26—H26A | 108.7 |
C9—C10—H10 | 118.9 | C25—C26—H26B | 108.7 |
C11—C10—C9 | 122.3 (3) | C25—C26—C27 | 114.3 (3) |
C11—C10—H10 | 118.9 | H26A—C26—H26B | 107.6 |
C6—C11—C14 | 122.1 (3) | C27—C26—H26A | 108.7 |
C10—C11—C6 | 118.1 (3) | C27—C26—H26B | 108.7 |
C10—C11—C14 | 119.8 (3) | C26—C27—H27 | 108.3 |
C7—C12—H12A | 109.5 | C28—C27—C26 | 108.9 (3) |
C7—C12—H12B | 109.5 | C28—C27—H27 | 108.3 |
C7—C12—H12C | 109.5 | C28—C27—C29 | 111.2 (3) |
H12A—C12—H12B | 109.5 | C29—C27—C26 | 111.8 (3) |
H12A—C12—H12C | 109.5 | C29—C27—H27 | 108.3 |
H12B—C12—H12C | 109.5 | C27—C28—H28A | 109.5 |
C9—C13—H13A | 109.5 | C27—C28—H28B | 109.5 |
C9—C13—H13B | 109.5 | C27—C28—H28C | 109.5 |
C9—C13—H13C | 109.5 | H28A—C28—H28B | 109.5 |
H13A—C13—H13B | 109.5 | H28A—C28—H28C | 109.5 |
H13A—C13—H13C | 109.5 | H28B—C28—H28C | 109.5 |
H13B—C13—H13C | 109.5 | C27—C29—H29A | 109.5 |
C11—C14—H14A | 109.5 | C27—C29—H29B | 109.5 |
C11—C14—H14B | 109.5 | C27—C29—H29C | 109.5 |
C11—C14—H14C | 109.5 | H29A—C29—H29B | 109.5 |
H14A—C14—H14B | 109.5 | H29A—C29—H29C | 109.5 |
H14A—C14—H14C | 109.5 | H29B—C29—H29C | 109.5 |
S1—C24—C25—O1 | 6.3 (4) | C6—C7—C8—C9 | 0.1 (5) |
S1—C24—C25—C26 | −173.5 (3) | C7—C6—C11—C10 | −3.3 (5) |
O1—C25—C26—C27 | 119.7 (4) | C7—C6—C11—C14 | 177.4 (3) |
N1—C15—C16—C17 | −177.1 (3) | C7—C8—C9—C10 | −2.5 (5) |
N1—C15—C16—C21 | 3.4 (5) | C7—C8—C9—C13 | 176.6 (3) |
N1—C15—C20—C19 | 177.0 (3) | C8—C9—C10—C11 | 2.1 (5) |
N1—C15—C20—C23 | −1.3 (5) | C9—C10—C11—C6 | 0.7 (5) |
N2—C2—C3—C4 | 52.3 (4) | C9—C10—C11—C14 | −180.0 (3) |
N2—C6—C7—C8 | −179.6 (3) | C11—C6—C7—C8 | 2.9 (5) |
N2—C6—C7—C12 | 0.6 (5) | C11—C6—C7—C12 | −176.9 (3) |
N2—C6—C11—C10 | 179.1 (3) | C12—C7—C8—C9 | 179.9 (3) |
N2—C6—C11—C14 | −0.1 (5) | C13—C9—C10—C11 | −177.0 (3) |
C1—S1—C24—C25 | −177.9 (2) | C15—N1—C1—S1 | 34.1 (4) |
C1—N1—C5—C4 | 28.3 (5) | C15—N1—C1—N2 | −152.8 (3) |
C1—N1—C15—C16 | −106.6 (4) | C15—N1—C5—C4 | −157.3 (3) |
C1—N1—C15—C20 | 77.8 (4) | C15—C16—C17—C18 | 0.6 (5) |
C1—N2—C2—C3 | −79.9 (4) | C16—C15—C20—C19 | 1.6 (5) |
C1—N2—C6—C7 | 75.7 (4) | C16—C15—C20—C23 | −176.7 (3) |
C1—N2—C6—C11 | −106.7 (4) | C16—C17—C18—C19 | 0.7 (5) |
C2—N2—C1—S1 | −174.2 (2) | C16—C17—C18—C22 | 179.1 (3) |
C2—N2—C1—N1 | 13.4 (5) | C17—C18—C19—C20 | −0.9 (5) |
C2—N2—C6—C7 | −108.4 (3) | C18—C19—C20—C15 | −0.2 (5) |
C2—N2—C6—C11 | 69.2 (4) | C18—C19—C20—C23 | 178.2 (3) |
C2—C3—C4—C5 | 33.1 (4) | C20—C15—C16—C17 | −1.8 (5) |
C3—C4—C5—N1 | −78.5 (4) | C20—C15—C16—C21 | 178.7 (3) |
C5—N1—C1—S1 | −151.9 (3) | C21—C16—C17—C18 | −179.9 (3) |
C5—N1—C1—N2 | 21.2 (5) | C22—C18—C19—C20 | −179.3 (3) |
C5—N1—C15—C16 | 78.5 (4) | C24—S1—C1—N1 | −131.5 (3) |
C5—N1—C15—C20 | −97.0 (4) | C24—S1—C1—N2 | 55.4 (3) |
C6—N2—C1—S1 | 1.5 (4) | C24—C25—C26—C27 | −60.5 (4) |
C6—N2—C1—N1 | −171.0 (3) | C25—C26—C27—C28 | −178.6 (3) |
C6—N2—C2—C3 | 104.1 (3) | C25—C26—C27—C29 | −55.3 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2A···I1 | 0.99 | 3.07 | 3.693 (3) | 122 |
C2—H2B···I2 | 0.99 | 3.17 | 3.986 (3) | 141 |
I3·C29H41N2OSe | Z = 2 |
Mr = 893.30 | F(000) = 860 |
Triclinic, P1 | Dx = 1.809 Mg m−3 |
a = 8.8091 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 14.2584 (8) Å | Cell parameters from 9322 reflections |
c = 15.1228 (9) Å | θ = 2.4–29.6° |
α = 63.952 (2)° | µ = 3.99 mm−1 |
β = 74.061 (2)° | T = 100 K |
γ = 81.113 (2)° | Block, red |
V = 1639.67 (17) Å3 | 0.17 × 0.11 × 0.08 mm |
Bruker D8 Venture Photon 2 diffractometer | 7989 reflections with I > 2σ(I) |
Radiation source: Incoatec IµS | Rint = 0.041 |
φ and ω scans | θmax = 29.6°, θmin = 2.4° |
Absorption correction: multi-scan SADABS v2016/2 (Bruker AXS Inc., 2017) | h = −12→12 |
Tmin = 0.640, Tmax = 0.746 | k = −19→19 |
75078 measured reflections | l = −21→21 |
9229 independent reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.024 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.052 | H-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 parameters | Δρmax = 1.18 e Å−3 |
0 restraints | Δρmin = −1.66 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
I1 | 0.56024 (2) | −0.00543 (2) | 0.26292 (2) | 0.03391 (5) | |
I2 | 0.72482 (2) | 0.19059 (2) | 0.17544 (2) | 0.01934 (4) | |
I3 | 0.89122 (2) | 0.38487 (2) | 0.08800 (2) | 0.02363 (4) | |
Se1 | 0.04429 (2) | 0.46632 (2) | 0.36803 (2) | 0.01641 (5) | |
O1 | −0.2198 (2) | 0.59460 (14) | 0.33074 (14) | 0.0274 (4) | |
N1 | 0.2595 (2) | 0.29977 (14) | 0.40427 (14) | 0.0139 (3) | |
N2 | 0.3824 (2) | 0.45914 (14) | 0.29884 (14) | 0.0135 (3) | |
C1 | 0.2541 (2) | 0.40347 (16) | 0.35019 (16) | 0.0134 (4) | |
C2 | 0.5407 (2) | 0.40814 (17) | 0.27903 (17) | 0.0169 (4) | |
H2A | 0.611534 | 0.460062 | 0.220870 | 0.020* | |
H2B | 0.530612 | 0.351443 | 0.260254 | 0.020* | |
C3 | 0.6152 (3) | 0.36290 (18) | 0.36972 (18) | 0.0181 (4) | |
H3A | 0.644487 | 0.420606 | 0.380685 | 0.022* | |
H3B | 0.712884 | 0.321943 | 0.355665 | 0.022* | |
C4 | 0.5016 (3) | 0.29243 (18) | 0.46569 (18) | 0.0178 (4) | |
H4A | 0.563658 | 0.241270 | 0.513273 | 0.021* | |
H4B | 0.434425 | 0.335673 | 0.498970 | 0.021* | |
C5 | 0.3967 (3) | 0.23407 (17) | 0.44382 (18) | 0.0166 (4) | |
H5A | 0.461021 | 0.208212 | 0.393546 | 0.020* | |
H5B | 0.356023 | 0.172588 | 0.506783 | 0.020* | |
C6 | 0.3759 (2) | 0.57255 (16) | 0.25038 (16) | 0.0129 (4) | |
C7 | 0.3547 (2) | 0.62997 (17) | 0.30804 (16) | 0.0143 (4) | |
C8 | 0.3491 (3) | 0.73870 (17) | 0.25717 (18) | 0.0168 (4) | |
H8 | 0.335672 | 0.779250 | 0.294784 | 0.020* | |
C9 | 0.3627 (3) | 0.78963 (17) | 0.15321 (18) | 0.0183 (4) | |
C10 | 0.3889 (3) | 0.72988 (18) | 0.09825 (17) | 0.0181 (4) | |
H10 | 0.401198 | 0.764083 | 0.026951 | 0.022* | |
C11 | 0.3978 (3) | 0.62098 (17) | 0.14482 (16) | 0.0159 (4) | |
C12 | 0.3429 (3) | 0.57902 (18) | 0.42043 (17) | 0.0184 (4) | |
H12A | 0.448886 | 0.557814 | 0.433104 | 0.028* | |
H12B | 0.278394 | 0.517385 | 0.451622 | 0.028* | |
H12C | 0.293679 | 0.628703 | 0.449676 | 0.028* | |
C13 | 0.3481 (3) | 0.90691 (19) | 0.1020 (2) | 0.0280 (5) | |
H13A | 0.246885 | 0.931139 | 0.133795 | 0.042* | |
H13B | 0.353046 | 0.928993 | 0.030135 | 0.042* | |
H13C | 0.434792 | 0.936981 | 0.108788 | 0.042* | |
C14 | 0.4265 (3) | 0.55979 (19) | 0.08152 (18) | 0.0226 (5) | |
H14A | 0.396947 | 0.603560 | 0.017142 | 0.034* | |
H14B | 0.362586 | 0.497658 | 0.117916 | 0.034* | |
H14C | 0.538605 | 0.538399 | 0.068364 | 0.034* | |
C15 | 0.1277 (2) | 0.23841 (16) | 0.42230 (17) | 0.0151 (4) | |
C16 | 0.1151 (3) | 0.21633 (17) | 0.34324 (17) | 0.0162 (4) | |
C17 | −0.0074 (3) | 0.15420 (18) | 0.36231 (18) | 0.0186 (4) | |
H17 | −0.018867 | 0.138494 | 0.309645 | 0.022* | |
C18 | −0.1138 (3) | 0.11430 (17) | 0.45592 (18) | 0.0182 (4) | |
C19 | −0.0950 (3) | 0.13699 (17) | 0.53315 (18) | 0.0182 (4) | |
H19 | −0.166541 | 0.109587 | 0.597502 | 0.022* | |
C20 | 0.0256 (3) | 0.19860 (17) | 0.51859 (17) | 0.0162 (4) | |
C21 | 0.2293 (3) | 0.2570 (2) | 0.24127 (18) | 0.0226 (5) | |
H21A | 0.215237 | 0.333100 | 0.207742 | 0.034* | |
H21B | 0.209252 | 0.225586 | 0.199650 | 0.034* | |
H21C | 0.337744 | 0.238655 | 0.250064 | 0.034* | |
C22 | −0.2434 (3) | 0.04532 (18) | 0.4740 (2) | 0.0220 (5) | |
H22A | −0.210789 | −0.028130 | 0.508358 | 0.033* | |
H22B | −0.263391 | 0.057748 | 0.409059 | 0.033* | |
H22C | −0.340088 | 0.061644 | 0.516426 | 0.033* | |
C23 | 0.0446 (3) | 0.2211 (2) | 0.60342 (18) | 0.0228 (5) | |
H23A | −0.047313 | 0.196810 | 0.660492 | 0.034* | |
H23B | 0.052815 | 0.296490 | 0.579708 | 0.034* | |
H23C | 0.140551 | 0.184659 | 0.625213 | 0.034* | |
C24 | 0.0241 (3) | 0.5622 (2) | 0.23151 (19) | 0.0282 (6) | |
H24A | 0.103682 | 0.616617 | 0.199786 | 0.034* | |
H24B | 0.037624 | 0.524216 | 0.188418 | 0.034* | |
C25 | −0.1416 (3) | 0.61029 (18) | 0.24598 (19) | 0.0205 (5) | |
C26 | −0.1997 (3) | 0.6772 (2) | 0.1516 (2) | 0.0254 (5) | |
H26A | −0.307891 | 0.704526 | 0.171166 | 0.030* | |
H26B | −0.205961 | 0.632844 | 0.117531 | 0.030* | |
C27 | −0.0959 (3) | 0.76942 (19) | 0.07604 (18) | 0.0226 (5) | |
H27 | 0.010448 | 0.741090 | 0.051836 | 0.027* | |
C28 | −0.1698 (4) | 0.8312 (2) | −0.0148 (2) | 0.0353 (7) | |
H28A | −0.183514 | 0.784491 | −0.043719 | 0.053* | |
H28B | −0.100331 | 0.887286 | −0.066010 | 0.053* | |
H28C | −0.272847 | 0.861528 | 0.007179 | 0.053* | |
C29 | −0.0746 (4) | 0.8387 (2) | 0.1248 (3) | 0.0398 (7) | |
H29A | −0.177981 | 0.866557 | 0.149714 | 0.060* | |
H29B | −0.007656 | 0.896625 | 0.074556 | 0.060* | |
H29C | −0.024420 | 0.797418 | 0.181449 | 0.060* |
U11 | U22 | U33 | U12 | U13 | U23 | |
I1 | 0.03473 (10) | 0.03072 (10) | 0.03661 (10) | −0.00860 (7) | −0.00581 (8) | −0.01347 (8) |
I2 | 0.01775 (7) | 0.02374 (8) | 0.01652 (7) | 0.00061 (5) | −0.00455 (5) | −0.00852 (6) |
I3 | 0.01934 (7) | 0.02508 (8) | 0.02477 (8) | −0.00127 (6) | −0.00152 (6) | −0.01089 (7) |
Se1 | 0.01227 (9) | 0.01410 (10) | 0.01832 (11) | 0.00093 (7) | −0.00392 (8) | −0.00298 (8) |
O1 | 0.0189 (8) | 0.0255 (9) | 0.0243 (9) | 0.0011 (7) | −0.0009 (7) | −0.0013 (7) |
N1 | 0.0127 (8) | 0.0116 (8) | 0.0175 (9) | 0.0005 (6) | −0.0067 (7) | −0.0047 (7) |
N2 | 0.0129 (8) | 0.0132 (8) | 0.0141 (8) | 0.0005 (6) | −0.0045 (7) | −0.0050 (7) |
C1 | 0.0137 (9) | 0.0131 (9) | 0.0150 (10) | 0.0015 (7) | −0.0065 (8) | −0.0062 (8) |
C2 | 0.0132 (9) | 0.0156 (10) | 0.0204 (11) | 0.0015 (8) | −0.0020 (8) | −0.0080 (9) |
C3 | 0.0150 (10) | 0.0159 (10) | 0.0229 (11) | 0.0006 (8) | −0.0072 (9) | −0.0065 (9) |
C4 | 0.0176 (10) | 0.0163 (10) | 0.0215 (11) | −0.0001 (8) | −0.0102 (9) | −0.0066 (9) |
C5 | 0.0156 (10) | 0.0119 (10) | 0.0219 (11) | 0.0015 (8) | −0.0093 (8) | −0.0043 (8) |
C6 | 0.0112 (9) | 0.0113 (9) | 0.0151 (10) | −0.0010 (7) | −0.0033 (7) | −0.0043 (8) |
C7 | 0.0110 (9) | 0.0151 (10) | 0.0166 (10) | −0.0005 (7) | −0.0036 (8) | −0.0062 (8) |
C8 | 0.0149 (10) | 0.0146 (10) | 0.0221 (11) | 0.0002 (8) | −0.0051 (8) | −0.0085 (9) |
C9 | 0.0162 (10) | 0.0138 (10) | 0.0217 (11) | −0.0016 (8) | −0.0052 (9) | −0.0037 (9) |
C10 | 0.0168 (10) | 0.0184 (11) | 0.0149 (10) | −0.0023 (8) | −0.0048 (8) | −0.0022 (9) |
C11 | 0.0147 (10) | 0.0187 (10) | 0.0135 (10) | 0.0002 (8) | −0.0044 (8) | −0.0056 (8) |
C12 | 0.0223 (11) | 0.0191 (11) | 0.0152 (10) | −0.0011 (9) | −0.0056 (8) | −0.0075 (9) |
C13 | 0.0322 (13) | 0.0155 (11) | 0.0295 (13) | −0.0036 (10) | −0.0079 (11) | −0.0021 (10) |
C14 | 0.0303 (12) | 0.0224 (12) | 0.0168 (11) | 0.0013 (10) | −0.0083 (10) | −0.0088 (9) |
C15 | 0.0146 (9) | 0.0109 (9) | 0.0212 (11) | 0.0003 (7) | −0.0081 (8) | −0.0060 (8) |
C16 | 0.0150 (10) | 0.0148 (10) | 0.0184 (10) | 0.0009 (8) | −0.0064 (8) | −0.0056 (8) |
C17 | 0.0190 (10) | 0.0180 (11) | 0.0235 (11) | 0.0011 (8) | −0.0105 (9) | −0.0101 (9) |
C18 | 0.0163 (10) | 0.0124 (10) | 0.0259 (12) | 0.0012 (8) | −0.0110 (9) | −0.0049 (9) |
C19 | 0.0154 (10) | 0.0145 (10) | 0.0209 (11) | −0.0009 (8) | −0.0042 (8) | −0.0039 (9) |
C20 | 0.0171 (10) | 0.0129 (10) | 0.0194 (11) | 0.0021 (8) | −0.0079 (8) | −0.0061 (8) |
C21 | 0.0225 (11) | 0.0290 (13) | 0.0187 (11) | −0.0047 (9) | −0.0042 (9) | −0.0113 (10) |
C22 | 0.0176 (10) | 0.0176 (11) | 0.0311 (13) | −0.0030 (8) | −0.0098 (10) | −0.0072 (10) |
C23 | 0.0234 (11) | 0.0260 (12) | 0.0214 (12) | −0.0052 (9) | −0.0046 (9) | −0.0111 (10) |
C24 | 0.0201 (11) | 0.0400 (15) | 0.0175 (11) | 0.0078 (10) | −0.0069 (9) | −0.0073 (11) |
C25 | 0.0151 (10) | 0.0165 (11) | 0.0241 (12) | −0.0020 (8) | −0.0060 (9) | −0.0020 (9) |
C26 | 0.0184 (11) | 0.0269 (13) | 0.0269 (13) | 0.0019 (9) | −0.0116 (10) | −0.0049 (10) |
C27 | 0.0223 (11) | 0.0213 (12) | 0.0187 (11) | 0.0035 (9) | −0.0032 (9) | −0.0059 (9) |
C28 | 0.0377 (15) | 0.0317 (15) | 0.0253 (13) | 0.0128 (12) | −0.0098 (12) | −0.0049 (12) |
C29 | 0.0489 (18) | 0.0298 (15) | 0.0427 (18) | −0.0024 (13) | −0.0096 (15) | −0.0172 (14) |
I1—I2 | 2.9351 (3) | C14—H14A | 0.9800 |
I2—I3 | 2.9230 (3) | C14—H14B | 0.9800 |
Se1—C1 | 1.928 (2) | C14—H14C | 0.9800 |
Se1—C24 | 1.952 (2) | C15—C16 | 1.398 (3) |
O1—C25 | 1.216 (3) | C15—C20 | 1.401 (3) |
N1—C1 | 1.340 (3) | C16—C17 | 1.390 (3) |
N1—C5 | 1.500 (3) | C16—C21 | 1.506 (3) |
N1—C15 | 1.456 (3) | C17—H17 | 0.9500 |
N2—C1 | 1.328 (3) | C17—C18 | 1.391 (3) |
N2—C2 | 1.487 (3) | C18—C19 | 1.397 (3) |
N2—C6 | 1.452 (3) | C18—C22 | 1.512 (3) |
C2—H2A | 0.9900 | C19—H19 | 0.9500 |
C2—H2B | 0.9900 | C19—C20 | 1.392 (3) |
C2—C3 | 1.521 (3) | C20—C23 | 1.508 (3) |
C3—H3A | 0.9900 | C21—H21A | 0.9800 |
C3—H3B | 0.9900 | C21—H21B | 0.9800 |
C3—C4 | 1.533 (3) | C21—H21C | 0.9800 |
C4—H4A | 0.9900 | C22—H22A | 0.9800 |
C4—H4B | 0.9900 | C22—H22B | 0.9800 |
C4—C5 | 1.518 (3) | C22—H22C | 0.9800 |
C5—H5A | 0.9900 | C23—H23A | 0.9800 |
C5—H5B | 0.9900 | C23—H23B | 0.9800 |
C6—C7 | 1.399 (3) | C23—H23C | 0.9800 |
C6—C11 | 1.402 (3) | C24—H24A | 0.9900 |
C7—C8 | 1.395 (3) | C24—H24B | 0.9900 |
C7—C12 | 1.506 (3) | C24—C25 | 1.515 (3) |
C8—H8 | 0.9500 | C25—C26 | 1.504 (3) |
C8—C9 | 1.391 (3) | C26—H26A | 0.9900 |
C9—C10 | 1.388 (3) | C26—H26B | 0.9900 |
C9—C13 | 1.505 (3) | C26—C27 | 1.533 (4) |
C10—H10 | 0.9500 | C27—H27 | 1.0000 |
C10—C11 | 1.395 (3) | C27—C28 | 1.529 (4) |
C11—C14 | 1.508 (3) | C27—C29 | 1.526 (4) |
C12—H12A | 0.9800 | C28—H28A | 0.9800 |
C12—H12B | 0.9800 | C28—H28B | 0.9800 |
C12—H12C | 0.9800 | C28—H28C | 0.9800 |
C13—H13A | 0.9800 | C29—H29A | 0.9800 |
C13—H13B | 0.9800 | C29—H29B | 0.9800 |
C13—H13C | 0.9800 | C29—H29C | 0.9800 |
I3—I2—I1 | 179.522 (8) | H14B—C14—H14C | 109.5 |
C1—Se1—C24 | 104.88 (10) | C16—C15—N1 | 117.64 (19) |
C1—N1—C5 | 126.80 (18) | C16—C15—C20 | 122.8 (2) |
C1—N1—C15 | 119.86 (17) | C20—C15—N1 | 119.43 (19) |
C15—N1—C5 | 113.14 (16) | C15—C16—C21 | 122.0 (2) |
C1—N2—C2 | 121.40 (18) | C17—C16—C15 | 117.3 (2) |
C1—N2—C6 | 122.66 (17) | C17—C16—C21 | 120.7 (2) |
C6—N2—C2 | 115.68 (17) | C16—C17—H17 | 118.9 |
N1—C1—Se1 | 113.47 (15) | C16—C17—C18 | 122.2 (2) |
N2—C1—Se1 | 122.89 (15) | C18—C17—H17 | 118.9 |
N2—C1—N1 | 123.18 (19) | C17—C18—C19 | 118.5 (2) |
N2—C2—H2A | 109.0 | C17—C18—C22 | 120.5 (2) |
N2—C2—H2B | 109.0 | C19—C18—C22 | 121.0 (2) |
N2—C2—C3 | 112.86 (18) | C18—C19—H19 | 119.0 |
H2A—C2—H2B | 107.8 | C20—C19—C18 | 121.9 (2) |
C3—C2—H2A | 109.0 | C20—C19—H19 | 119.0 |
C3—C2—H2B | 109.0 | C15—C20—C23 | 121.7 (2) |
C2—C3—H3A | 109.4 | C19—C20—C15 | 117.3 (2) |
C2—C3—H3B | 109.4 | C19—C20—C23 | 121.0 (2) |
C2—C3—C4 | 111.36 (18) | C16—C21—H21A | 109.5 |
H3A—C3—H3B | 108.0 | C16—C21—H21B | 109.5 |
C4—C3—H3A | 109.4 | C16—C21—H21C | 109.5 |
C4—C3—H3B | 109.4 | H21A—C21—H21B | 109.5 |
C3—C4—H4A | 109.1 | H21A—C21—H21C | 109.5 |
C3—C4—H4B | 109.1 | H21B—C21—H21C | 109.5 |
H4A—C4—H4B | 107.8 | C18—C22—H22A | 109.5 |
C5—C4—C3 | 112.51 (19) | C18—C22—H22B | 109.5 |
C5—C4—H4A | 109.1 | C18—C22—H22C | 109.5 |
C5—C4—H4B | 109.1 | H22A—C22—H22B | 109.5 |
N1—C5—C4 | 113.31 (17) | H22A—C22—H22C | 109.5 |
N1—C5—H5A | 108.9 | H22B—C22—H22C | 109.5 |
N1—C5—H5B | 108.9 | C20—C23—H23A | 109.5 |
C4—C5—H5A | 108.9 | C20—C23—H23B | 109.5 |
C4—C5—H5B | 108.9 | C20—C23—H23C | 109.5 |
H5A—C5—H5B | 107.7 | H23A—C23—H23B | 109.5 |
C7—C6—N2 | 120.19 (19) | H23A—C23—H23C | 109.5 |
C7—C6—C11 | 122.0 (2) | H23B—C23—H23C | 109.5 |
C11—C6—N2 | 117.75 (19) | Se1—C24—H24A | 110.8 |
C6—C7—C12 | 122.61 (19) | Se1—C24—H24B | 110.8 |
C8—C7—C6 | 117.5 (2) | H24A—C24—H24B | 108.9 |
C8—C7—C12 | 119.9 (2) | C25—C24—Se1 | 104.59 (16) |
C7—C8—H8 | 118.9 | C25—C24—H24A | 110.8 |
C9—C8—C7 | 122.1 (2) | C25—C24—H24B | 110.8 |
C9—C8—H8 | 118.9 | O1—C25—C24 | 119.9 (2) |
C8—C9—C13 | 120.5 (2) | O1—C25—C26 | 123.4 (2) |
C10—C9—C8 | 118.5 (2) | C26—C25—C24 | 116.6 (2) |
C10—C9—C13 | 121.0 (2) | C25—C26—H26A | 108.7 |
C9—C10—H10 | 119.1 | C25—C26—H26B | 108.7 |
C9—C10—C11 | 121.8 (2) | C25—C26—C27 | 114.3 (2) |
C11—C10—H10 | 119.1 | H26A—C26—H26B | 107.6 |
C6—C11—C14 | 122.5 (2) | C27—C26—H26A | 108.7 |
C10—C11—C6 | 117.9 (2) | C27—C26—H26B | 108.7 |
C10—C11—C14 | 119.6 (2) | C26—C27—H27 | 108.3 |
C7—C12—H12A | 109.5 | C28—C27—C26 | 108.7 (2) |
C7—C12—H12B | 109.5 | C28—C27—H27 | 108.3 |
C7—C12—H12C | 109.5 | C29—C27—C26 | 111.7 (2) |
H12A—C12—H12B | 109.5 | C29—C27—H27 | 108.3 |
H12A—C12—H12C | 109.5 | C29—C27—C28 | 111.4 (2) |
H12B—C12—H12C | 109.5 | C27—C28—H28A | 109.5 |
C9—C13—H13A | 109.5 | C27—C28—H28B | 109.5 |
C9—C13—H13B | 109.5 | C27—C28—H28C | 109.5 |
C9—C13—H13C | 109.5 | H28A—C28—H28B | 109.5 |
H13A—C13—H13B | 109.5 | H28A—C28—H28C | 109.5 |
H13A—C13—H13C | 109.5 | H28B—C28—H28C | 109.5 |
H13B—C13—H13C | 109.5 | C27—C29—H29A | 109.5 |
C11—C14—H14A | 109.5 | C27—C29—H29B | 109.5 |
C11—C14—H14B | 109.5 | C27—C29—H29C | 109.5 |
C11—C14—H14C | 109.5 | H29A—C29—H29B | 109.5 |
H14A—C14—H14B | 109.5 | H29A—C29—H29C | 109.5 |
H14A—C14—H14C | 109.5 | H29B—C29—H29C | 109.5 |
Se1—C24—C25—O1 | 8.9 (3) | C6—C7—C8—C9 | 0.5 (3) |
Se1—C24—C25—C26 | −171.74 (18) | C7—C6—C11—C10 | −3.6 (3) |
O1—C25—C26—C27 | 121.8 (3) | C7—C6—C11—C14 | 177.8 (2) |
N1—C15—C16—C17 | 177.50 (19) | C7—C8—C9—C10 | −2.6 (3) |
N1—C15—C16—C21 | −2.1 (3) | C7—C8—C9—C13 | 176.9 (2) |
N1—C15—C20—C19 | −177.53 (19) | C8—C9—C10—C11 | 1.7 (3) |
N1—C15—C20—C23 | 2.5 (3) | C9—C10—C11—C6 | 1.3 (3) |
N2—C2—C3—C4 | 51.5 (2) | C9—C10—C11—C14 | −180.0 (2) |
N2—C6—C7—C8 | −179.91 (18) | C11—C6—C7—C8 | 2.7 (3) |
N2—C6—C7—C12 | 2.0 (3) | C11—C6—C7—C12 | −175.4 (2) |
N2—C6—C11—C10 | 178.95 (18) | C12—C7—C8—C9 | 178.7 (2) |
N2—C6—C11—C14 | 0.3 (3) | C13—C9—C10—C11 | −177.9 (2) |
C1—N1—C5—C4 | 29.1 (3) | C15—N1—C1—Se1 | 33.5 (2) |
C1—N1—C15—C16 | 77.8 (3) | C15—N1—C1—N2 | −154.0 (2) |
C1—N1—C15—C20 | −106.3 (2) | C15—N1—C5—C4 | −156.09 (19) |
C1—N2—C2—C3 | −79.4 (2) | C15—C16—C17—C18 | −0.4 (3) |
C1—N2—C6—C7 | 77.7 (3) | C16—C15—C20—C19 | −1.8 (3) |
C1—N2—C6—C11 | −104.7 (2) | C16—C15—C20—C23 | 178.2 (2) |
C2—N2—C1—Se1 | −174.64 (15) | C16—C17—C18—C19 | −0.6 (3) |
C2—N2—C1—N1 | 13.6 (3) | C16—C17—C18—C22 | −178.8 (2) |
C2—N2—C6—C7 | −108.1 (2) | C17—C18—C19—C20 | 0.5 (3) |
C2—N2—C6—C11 | 69.4 (2) | C18—C19—C20—C15 | 0.6 (3) |
C2—C3—C4—C5 | 33.7 (3) | C18—C19—C20—C23 | −179.4 (2) |
C3—C4—C5—N1 | −79.3 (2) | C20—C15—C16—C17 | 1.7 (3) |
C5—N1—C1—Se1 | −152.00 (17) | C20—C15—C16—C21 | −177.9 (2) |
C5—N1—C1—N2 | 20.5 (3) | C21—C16—C17—C18 | 179.2 (2) |
C5—N1—C15—C16 | −97.4 (2) | C22—C18—C19—C20 | 178.7 (2) |
C5—N1—C15—C20 | 78.6 (2) | C24—C25—C26—C27 | −57.6 (3) |
C6—N2—C1—Se1 | −0.8 (3) | C25—C26—C27—C28 | −179.1 (2) |
C6—N2—C1—N1 | −172.55 (19) | C25—C26—C27—C29 | −55.8 (3) |
C6—N2—C2—C3 | 106.4 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2A···I3 | 0.99 | 3.10 | 3.690 (2) | 120 |
C2—H2B···I2 | 0.99 | 3.16 | 4.003 (2) | 144 |
C3—H3A···O1i | 0.99 | 2.63 | 3.560 (3) | 156 |
Symmetry code: (i) x+1, y, z. |
C6F4I2·C23H30N2S | Dx = 1.765 Mg m−3 |
Mr = 768.41 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pna21 | Cell parameters from 9353 reflections |
a = 7.6668 (5) Å | θ = 2.9–28.4° |
b = 16.8546 (11) Å | µ = 2.30 mm−1 |
c = 22.3786 (15) Å | T = 100 K |
V = 2891.8 (3) Å3 | Needle, colourless |
Z = 4 | 0.22 × 0.07 × 0.07 mm |
F(000) = 1504 |
Bruker D8 Venture Photon 2 diffractometer | 6786 reflections with I > 2σ(I) |
Radiation source: Incoatec IµS | Rint = 0.044 |
φ and ω scans | θmax = 28.4°, θmin = 2.9° |
Absorption correction: multi-scan SADABS v2016/2 (Bruker AXS Inc., 2017) | h = −10→10 |
Tmin = 0.621, Tmax = 0.746 | k = −22→22 |
50096 measured reflections | l = −29→29 |
7186 independent reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.025 | H-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 reflections | Δρmax = 0.77 e Å−3 |
349 parameters | Δρmin = −0.70 e Å−3 |
1 restraint | Absolute 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: dual | Absolute structure parameter: −0.025 (7) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
I1 | 0.76980 (3) | 0.62670 (2) | 0.46051 (2) | 0.02765 (7) | |
I2 | 0.97868 (5) | 0.51579 (2) | 0.33758 (2) | 0.04162 (10) | |
S1 | 0.60961 (14) | 0.55911 (7) | 0.58283 (5) | 0.0232 (2) | |
F1 | 1.1171 (5) | 0.6411 (2) | 0.24692 (15) | 0.0512 (9) | |
F2 | 1.1071 (5) | 0.8009 (2) | 0.24353 (15) | 0.0501 (9) | |
F3 | 0.9486 (4) | 0.88308 (16) | 0.33257 (17) | 0.0420 (8) | |
F4 | 0.8078 (4) | 0.80691 (16) | 0.42584 (13) | 0.0328 (6) | |
N1 | 0.3091 (5) | 0.5365 (2) | 0.63715 (19) | 0.0265 (8) | |
N2 | 0.3786 (5) | 0.4428 (2) | 0.5645 (2) | 0.0305 (9) | |
C1 | 0.4198 (6) | 0.5102 (2) | 0.5951 (2) | 0.0200 (9) | |
C2 | 0.1806 (8) | 0.4819 (4) | 0.6655 (3) | 0.0432 (14) | |
H2A | 0.229976 | 0.427654 | 0.667154 | 0.052* | |
H2B | 0.157212 | 0.499472 | 0.706911 | 0.052* | |
C3 | 0.0158 (8) | 0.4806 (4) | 0.6313 (3) | 0.0493 (16) | |
H3A | −0.046060 | 0.531689 | 0.636781 | 0.059* | |
H3B | −0.060145 | 0.437740 | 0.646715 | 0.059* | |
C4 | 0.0508 (7) | 0.4673 (4) | 0.5657 (3) | 0.0431 (14) | |
H4A | 0.080531 | 0.518610 | 0.546703 | 0.052* | |
H4B | −0.056322 | 0.446880 | 0.546392 | 0.052* | |
C5 | 0.2001 (8) | 0.4085 (4) | 0.5554 (3) | 0.0487 (15) | |
H5A | 0.185025 | 0.362981 | 0.582901 | 0.058* | |
H5B | 0.191928 | 0.387880 | 0.514045 | 0.058* | |
C6 | 0.3364 (6) | 0.6117 (3) | 0.6666 (2) | 0.0232 (9) | |
C7 | 0.4201 (6) | 0.6116 (3) | 0.7220 (2) | 0.0224 (9) | |
C8 | 0.4381 (6) | 0.6831 (3) | 0.7517 (2) | 0.0237 (9) | |
H8 | 0.492427 | 0.683636 | 0.789888 | 0.028* | |
C9 | 0.3790 (5) | 0.7543 (3) | 0.72750 (19) | 0.0215 (8) | |
C10 | 0.2966 (6) | 0.7529 (3) | 0.6722 (2) | 0.0233 (9) | |
H10 | 0.255033 | 0.800920 | 0.655168 | 0.028* | |
C11 | 0.2742 (6) | 0.6814 (3) | 0.6412 (2) | 0.0240 (9) | |
C12 | 0.4979 (7) | 0.5365 (3) | 0.7482 (2) | 0.0328 (11) | |
H12A | 0.566656 | 0.549750 | 0.783683 | 0.049* | |
H12B | 0.573296 | 0.511151 | 0.718387 | 0.049* | |
H12C | 0.403853 | 0.499932 | 0.759285 | 0.049* | |
C13 | 0.4087 (7) | 0.8325 (3) | 0.7592 (2) | 0.0290 (10) | |
H13A | 0.355962 | 0.830439 | 0.799039 | 0.043* | |
H13B | 0.355066 | 0.875461 | 0.736079 | 0.043* | |
H13C | 0.534227 | 0.842229 | 0.762911 | 0.043* | |
C14 | 0.1852 (7) | 0.6816 (3) | 0.5808 (2) | 0.0359 (11) | |
H14A | 0.265106 | 0.660354 | 0.550567 | 0.054* | |
H14B | 0.152644 | 0.736009 | 0.570130 | 0.054* | |
H14C | 0.080179 | 0.648495 | 0.582509 | 0.054* | |
C15 | 0.5100 (6) | 0.4061 (3) | 0.5274 (2) | 0.0246 (9) | |
C16 | 0.5122 (6) | 0.4250 (3) | 0.4669 (2) | 0.0298 (10) | |
C17 | 0.6364 (8) | 0.3875 (3) | 0.4312 (2) | 0.0357 (12) | |
H17 | 0.641079 | 0.400304 | 0.389903 | 0.043* | |
C18 | 0.7511 (7) | 0.3334 (3) | 0.4533 (3) | 0.0339 (12) | |
C19 | 0.7444 (7) | 0.3146 (3) | 0.5140 (3) | 0.0327 (11) | |
H19 | 0.823037 | 0.276326 | 0.529601 | 0.039* | |
C20 | 0.6242 (7) | 0.3511 (3) | 0.5523 (2) | 0.0262 (10) | |
C21 | 0.3875 (9) | 0.4837 (3) | 0.4399 (3) | 0.0436 (14) | |
H21A | 0.269598 | 0.461286 | 0.439790 | 0.065* | |
H21B | 0.423136 | 0.495468 | 0.398751 | 0.065* | |
H21C | 0.388556 | 0.532697 | 0.463461 | 0.065* | |
C22 | 0.8837 (10) | 0.2938 (4) | 0.4130 (3) | 0.0569 (18) | |
H22A | 0.848212 | 0.300223 | 0.371173 | 0.085* | |
H22B | 0.890619 | 0.237185 | 0.422639 | 0.085* | |
H22C | 0.998228 | 0.318399 | 0.418976 | 0.085* | |
C23 | 0.6163 (8) | 0.3323 (3) | 0.6176 (2) | 0.0380 (12) | |
H23A | 0.716140 | 0.298929 | 0.628511 | 0.057* | |
H23B | 0.507779 | 0.303869 | 0.626396 | 0.057* | |
H23C | 0.620007 | 0.381638 | 0.640710 | 0.057* | |
C24 | 0.8881 (6) | 0.6816 (3) | 0.3862 (2) | 0.0245 (9) | |
C25 | 0.9652 (6) | 0.6393 (3) | 0.3394 (3) | 0.0286 (9) | |
C26 | 1.0380 (7) | 0.6802 (4) | 0.2921 (2) | 0.0347 (12) | |
C27 | 1.0339 (7) | 0.7622 (4) | 0.2899 (2) | 0.0349 (12) | |
C28 | 0.9552 (6) | 0.8040 (3) | 0.3352 (3) | 0.0304 (10) | |
C29 | 0.8843 (6) | 0.7634 (3) | 0.3828 (2) | 0.0263 (9) |
U11 | U22 | U33 | U12 | U13 | U23 | |
I1 | 0.02956 (14) | 0.02609 (13) | 0.02730 (13) | −0.00367 (11) | −0.00535 (16) | 0.00388 (13) |
I2 | 0.0456 (2) | 0.03001 (16) | 0.0492 (2) | 0.00803 (14) | −0.01249 (18) | −0.01082 (18) |
S1 | 0.0195 (5) | 0.0228 (5) | 0.0272 (5) | −0.0043 (4) | 0.0023 (4) | −0.0038 (4) |
F1 | 0.055 (2) | 0.066 (2) | 0.0320 (17) | 0.0002 (18) | 0.0085 (15) | −0.0162 (17) |
F2 | 0.053 (2) | 0.070 (2) | 0.0273 (16) | −0.0194 (19) | 0.0003 (15) | 0.0126 (16) |
F3 | 0.0516 (19) | 0.0291 (14) | 0.0452 (19) | −0.0074 (13) | −0.0098 (16) | 0.0117 (15) |
F4 | 0.0375 (16) | 0.0265 (14) | 0.0343 (16) | −0.0003 (12) | 0.0019 (13) | −0.0042 (12) |
N1 | 0.0236 (19) | 0.0231 (19) | 0.033 (2) | −0.0070 (15) | 0.0090 (16) | −0.0065 (16) |
N2 | 0.0211 (19) | 0.029 (2) | 0.042 (2) | −0.0035 (16) | 0.0062 (17) | −0.0102 (18) |
C1 | 0.018 (2) | 0.0169 (19) | 0.025 (2) | 0.0008 (15) | −0.0025 (16) | 0.0050 (16) |
C2 | 0.040 (3) | 0.042 (3) | 0.048 (3) | −0.009 (3) | 0.009 (3) | 0.000 (3) |
C3 | 0.033 (3) | 0.049 (4) | 0.065 (4) | 0.001 (3) | 0.006 (3) | −0.001 (3) |
C4 | 0.028 (3) | 0.037 (3) | 0.065 (4) | 0.000 (2) | −0.008 (3) | −0.006 (3) |
C5 | 0.036 (3) | 0.041 (3) | 0.070 (4) | −0.008 (3) | −0.002 (3) | −0.013 (3) |
C6 | 0.023 (2) | 0.022 (2) | 0.025 (2) | −0.0039 (17) | 0.0050 (17) | −0.0035 (17) |
C7 | 0.025 (2) | 0.021 (2) | 0.021 (2) | 0.0015 (17) | 0.0059 (17) | 0.0036 (16) |
C8 | 0.025 (2) | 0.029 (2) | 0.018 (2) | 0.0015 (18) | −0.0009 (16) | 0.0001 (17) |
C9 | 0.019 (2) | 0.024 (2) | 0.021 (2) | 0.0004 (16) | 0.0032 (16) | −0.0038 (17) |
C10 | 0.022 (2) | 0.025 (2) | 0.023 (2) | 0.0053 (17) | 0.0049 (17) | 0.0019 (18) |
C11 | 0.020 (2) | 0.031 (2) | 0.021 (2) | 0.0016 (18) | −0.0005 (17) | −0.0008 (18) |
C12 | 0.039 (3) | 0.025 (2) | 0.035 (3) | 0.005 (2) | 0.003 (2) | 0.010 (2) |
C13 | 0.030 (2) | 0.024 (2) | 0.034 (3) | 0.0003 (19) | −0.001 (2) | −0.0079 (19) |
C14 | 0.039 (3) | 0.040 (3) | 0.029 (2) | 0.009 (2) | −0.008 (2) | −0.002 (2) |
C15 | 0.027 (2) | 0.018 (2) | 0.029 (2) | −0.0045 (17) | 0.0021 (18) | −0.0069 (17) |
C16 | 0.037 (2) | 0.021 (2) | 0.032 (3) | −0.0034 (17) | −0.007 (2) | −0.003 (2) |
C17 | 0.060 (4) | 0.025 (2) | 0.022 (2) | −0.008 (2) | 0.003 (2) | −0.0034 (19) |
C18 | 0.042 (3) | 0.025 (2) | 0.035 (3) | 0.0017 (19) | 0.014 (2) | −0.006 (2) |
C19 | 0.035 (3) | 0.021 (2) | 0.042 (3) | 0.005 (2) | 0.000 (2) | −0.005 (2) |
C20 | 0.034 (3) | 0.020 (2) | 0.025 (2) | −0.0043 (18) | 0.0059 (19) | −0.0005 (17) |
C21 | 0.050 (3) | 0.033 (3) | 0.048 (3) | 0.000 (2) | −0.021 (3) | −0.001 (2) |
C22 | 0.071 (5) | 0.045 (4) | 0.055 (4) | 0.011 (3) | 0.027 (4) | −0.006 (3) |
C23 | 0.051 (3) | 0.033 (3) | 0.030 (3) | −0.005 (2) | 0.002 (2) | 0.004 (2) |
C24 | 0.026 (2) | 0.025 (2) | 0.023 (2) | −0.0027 (18) | −0.0068 (18) | 0.0032 (18) |
C25 | 0.027 (2) | 0.031 (2) | 0.028 (2) | 0.0016 (18) | −0.008 (2) | −0.001 (2) |
C26 | 0.034 (3) | 0.049 (3) | 0.022 (2) | 0.000 (2) | −0.004 (2) | −0.007 (2) |
C27 | 0.036 (3) | 0.046 (3) | 0.023 (2) | −0.011 (2) | −0.007 (2) | 0.008 (2) |
C28 | 0.029 (2) | 0.030 (2) | 0.033 (2) | −0.0037 (18) | −0.011 (2) | 0.009 (2) |
C29 | 0.024 (2) | 0.027 (2) | 0.027 (2) |