sigma-hole interactions
Halogen, chalcogen, and hydrogen bonding in organoiodine cocrystals of heterocyclic thiones: imidazolidine-2-thione, 2-mercaptobenzimidazole, 2-mercapto-5-methylbenzimidazole, 2-mercaptobenzoxazole, and 2-mercaptobenzothiazole
aDepartment of Chemistry, Clemson University, 219 Hunter Laboratories, Clemson, SC 29634, USA
*Correspondence e-mail: billp@clemson.edu
Through the combination of heterocyclic thiones with variation in the identity of the heterocyclic elements, namely, imidazolidine-2-thione, 2-mercaptobenzimidazole, 2-mercapto-5-methylbenzimidazole, 2-mercaptobenzoxazole, and 2-mercaptobenzothiazole with the common halogen-bond donors 1,2-, 1,3-, and 1,4-diiodotetrafluorobenzene, 1,3,5-trifluorotriiodobenzene, and tetraiodoethylene, a series of 18 new crystalline structures were characterized. In most cases, N—H⋯S hydrogen bonding was observed, with these interactions in imidazole-containing structures typically resulting in two-dimensional motifs (i.e. ribbons). Lacking the second N—H group, the thiazole and oxazole hydrogen bonding resulted in only dimeric pairs. C—I⋯S and C—I⋯I halogen bonding, as well as C=S⋯I chalcogen bonding, served to consolidate the packing by linking the hydrogen-bonding ribbons or dimeric pairs.
Keywords: crystal structure; halogen bonding; organoiodine; chalcogen bonding; hydrogen bonding; thione.
1. Introduction
Halogen and chalcogen bonding, defined by IUPAC as `a net attractive interaction between an electrophilic region associated with…' a halogen or chalcogen atom, respectively, `…in a molecular entity and a nucleophilic region in another, or the same, molecular entity (Desiraju et al., 2013; Aakeroy et al., 2019),' has drawn increasing attention in recent years (Parisini et al., 2011; Zhou et al., 2010; Ajani et al., 2015; Arman et al., 2008; Aakeroy et al., 2015; Metrangolo & Resnati, 2012; Cavallo et al., 2016; Metrangolo et al., 2005; Legon, 1998). Similar to hydrogen bonding, halogen bonding is strong, selective, and directional. Organic iodines are among the most commonly utilized halogen-bond donors (Corradi et al., 2000), largely due to their greater polarizability. When paired with halogen-bond acceptor molecules with a diversity of heteroatoms, the combined effects of halogen, chalcogen, and hydrogen bonding can be revealed. Imidazoles, thiazoles, and oxazoles are ideal systems to study in this regard.
Benzimidazole, and its derivatives, have been investigated for a diverse range of biological applications, including in the treatment of tuberculosis (Foks et al., 2006), as antimicrobial agents (Alasmary et al., 2015), and also as analgesic and anti-inflammatory compounds (Achar et al., 2010; Fletcher et al., 2006). These mercaptobenzimidazoles, thiazoles, and oxazoles have also seen significant utilization as ligands in transition-metal complexes. Providing some insight into the role of heteroatoms in differing positions, of the 31 crystal structures containing 2-mercaptobenzothiazole (MBZTH) and a transition metal currently deposited with the Cambridge Structural Database (CSD; Groom et al., 2016), all demonstrate metal coordination through the thione S atom and not the thiazole S atom. They range from simple species, such as (2-mercaptobenzothiazole)bis(triphenylphosphine)silver(I) iodide (Banti et al., 2014), to more complex copper and ruthenium complexes (Zhou et al., 2013a; Zafar et al., 2019). Similarly, the mercaptobenzimidazole (or benzimidazolethione) derivatives present an interesting field of study for their potential intermolecular interactions in halogen-bonding systems (Fig. 1). In these systems, hydrogen, halogen, and chalcogen bonding are all viable intermolecular interactions, and structural studies of the cocrystals can be useful in determining which interactions are preferred as the organoiodine and the heterocyclic systems are varied.
Our group has recently been interested in the role of the S atom in I⋯S halogen- and chalcogen-bonding interactions as a crystal design tool, as well as their roles in the formation of deep eutectic solvents derived from halogen bonding (Peloquin et al., 2021a,b,c,d, 2022). Herein, we report the solid-state structures of 18 new cocrystals derived from the combination of the heterocyclic molecules imidazolidine-2-thione (IT), 2-mercaptobenzimidazole (MBZIM), 2-mercapto-5-methylbenzimidazole (MMBZIM), 2-mercaptobenzoxazole (MBZOX), and 2-mercaptobenzothiazole (MBZTH) with the organic halogen-bond donors 1,2-diiodotetrafluorobenzene (1,2-F4DIB), 1,3-diiodotetrafluorobenzene (1,3-F4DIB), 1,4-tetrafluorobenzene (1,4-F4DIB), 1,3,5-trifluoro-2,4,6-triiodobenzene (1,3,5-F3I3B), and tetraiodoethylene (TIE). This diverse pool of substrates yielded structures with the crystal packing dominated by N—H⋯S hydrogen bonding, leading to thioamide dimers, with longer-range packing motifs created through C—I⋯S and C—I⋯I halogen bonding, as well as the occasional C=S⋯I chalcogen bond.
2. Experimental
2.1. Materials and instrumentation
For single-crystal X-ray analysis, crystals were mounted on low background cryogenic loops using paratone oil. Data were collected 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.
2.2. Preparation of cocrystals
Cocrystals were synthesized using imidazolidine-2-thione (TCI Americas, 98%), 2-mercaptobenzimidazole (Acros, 98%), 2-mercapto-5-methylbenzimidazole (Acros, 99%), 2-mercaptobenzoxazole (Acros, 99%), 2-mercaptobenzothiazole (Acros, 98%), 1,2-diiodotetrafluorobenzene (Synquest Laboratories, 99%), 1,3-diiodotetrafluorobenzene (Synquest Laboratories, 97%), 1,4-tetrafluorobenzene (Synquest Laboratories, 97%), 1,3,5-trifluoro-2,4,6-triiodobenzene (Synquest Laboratories, 99%), and tetraiodoethylene (Santa Cruz Biotechnologies, 98%). Solvents were obtained from Fisher Scientific. All materials were used as received without further purification. Crystals were formed by slow evaporation under ambient conditions (20–23 °C). Methanol was utilized for the majority of cocrystal preparations; however, if this was not successful, acetone or ethyl acetate was utilized.
2.2.1. 2(IT)·(1,3-F4DIB)
Imidazolidine-2-thione (50 mg, 0.489 mmol) and 1,3-diiodotetrafluorobenzene (196 mg, 0.489 mmol) were weighed into a 20 ml glass vial. Methanol (10 ml) was added and the mixture was stirred until a clear solution was obtained. The solvent was allowed to evaporate slowly and colorless needle-like crystals of 2(IT)·(1,3-F4DIB) were obtained after 3 d.
2.2.2. (IT)·(1,3,5-F3I3B)
Imidazolidine-2-thione (50 mg, 0.489 mmol) and 1,3,5-trifluoro-2,4,6-triiodobenzene (249 mg, 0.489 mmol) were weighed into a 20 ml glass vial. Methanol (10 ml) was added and the mixture was stirred until a clear solution was obtained. The solvent was allowed to evaporate slowly and colorless needle-like crystals of (IT)·(1,3,5-F3I3B) were obtained after 4 d.
2.2.3. 4(MBZIM)·3(1,3-F4DIB)
2-Mercaptobenzimidazole (34 mg, 0.227 mmol) and 1,3-diiodotetrafluorobenzene (49 mg, 0.122 mmol) were weighed into a 20 ml glass vial. Methanol (10 ml) was added and the mixture was stirred until a clear solution was obtained. The solvent was allowed to evaporate slowly and colorless needle-like crystals of 4(MBZIM)·3(1,3-F4DIB) were obtained after 4 d.
2.2.4. (MBZIM)·(1,4-F4DIB)
2-Mercaptobenzimidazole (19 mg, 0.126 mmol) and 1,4-diiodotetrafluorobenzene (50 mg, 0.124 mmol) were weighed into a 20 ml glass vial. Methanol (10 ml) was added and the mixture was stirred until a clear solution was obtained. The solvent was allowed to evaporate slowly and colorless plate-like crystals of (MBZIM)·(1,4-F4DIB) were obtained after 3 d.
2.2.5. (MBZIM)·(TIE)
2-Mercaptobenzimidazole (30 mg, 0.200 mmol) and tetraiodoethylene (55 mg, 0.103 mmol) were weighed into a 20 ml glass vial. Ethyl acetate (15 ml) was added and the mixture was stirred until a clear solution was obtained. The solvent was allowed to evaporate slowly and colorless tabular crystals of (MBZIM)·(TIE) were obtained after 7 d.
2.2.6. (MMBZIM)·(1,2-F4DIB)
2-Mercapto-5-methylbenzimidazole (20 mg, 0.122 mmol) and 1,2-diiodotetrafluorobenzene (48 mg, 0.119 mmol) were weighed into a 20 ml glass vial. Methanol (10 ml) was added and the mixture was stirred until a clear solution was obtained. The solvent was allowed to evaporate slowly and colorless columnar crystals of (MMBZIM)·(1,2-F4DIB) were obtained after 3 d.
2.2.7. 2(MMBZIM)·(1,4-F4DIB)·2(H2O)
2-Mercapto-5-methylbenzimidazole (40 mg, 0.244 mmol) and 1,4-diiodotetrafluorobenzene (51 mg, 0.127 mmol) were weighed into a 20 ml glass vial. Methanol (10 ml) was added and the mixture was stirred until a clear solution was obtained. The solvent was allowed to evaporate slowly and colorless plate-like crystals of 2(MMBZIM)·(1,4-F4DIB)·2(H2O) were obtained after 3 d.
2.2.8. (MMBZIM)·(1,3,5-F3I3B)
2-Mercapto-5-methylbenzimidazole (31 mg, 0.189 mmol) and 1,3,5-trifluoro-2,4,6-triiodobenzene (50 mg, 0.098 mmol) were weighed into a 20 ml glass vial. Methanol (10 ml) was added and the mixture was stirred until a clear solution was obtained. The solvent was allowed to evaporate slowly and colorless needle-like crystals of (MMBZIM)·(1,3,5-F3I3B) were obtained after 4 d.
2.2.9. (MBZOX)·(1,2-F4DIB)
2-Mercaptobenzoxazole (20 mg, 0.132 mmol) and 1,2-diiodotetrafluorobenzene (102 mg, 0.254 mmol) were weighed into a 20 ml glass vial. Methanol (10 ml) was added and the mixture was stirred until a clear solution was obtained. The solvent was allowed to evaporate slowly and colorless needle-like crystals of (MBZOX)·(1,2-F4DIB) were obtained after 3 d.
2.2.10. (MBZOX)·(1,3-F4DIB)
2-Mercaptobenzoxazole (19 mg, 0.126 mmol) and 1,3-diiodotetrafluorobenzene (104 mg, 0.259 mmol) were weighed into a 20 ml glass vial. Acetone (10 ml) was added and the mixture was stirred until a clear solution was obtained. The solvent was allowed to evaporate slowly and colorless columnar crystals of (MBZOX)·(1,3-F4DIB) were obtained after 2 d.
2.2.11. 2(MBZOX)·(1,4-F4DIB)
2-Mercaptobenzoxazole (40 mg, 0.265 mmol) and 1,4-diiodotetrafluorobenzene (50 mg, 0.124 mmol) were weighed into a 20 ml glass vial. Acetone (10 ml) was added and the mixture was stirred until a clear solution was obtained. The solvent was allowed to evaporate slowly and colorless columnar crystals of 2(MBZOX)·(1,4-F4DIB) were obtained after 2 d.
2.2.12. (MBZOX)·(1,3,5-F3I3B)
2-Mercaptobenzoxazole (15 mg, 0.099 mmol) and 1,3,5-trifluoro-2,4,6-triiodobenzene (50 mg, 0.098 mmol) were weighed into a 20 ml glass vial. Acetone (10 ml) was added and the mixture was stirred until a clear solution was obtained. The solvent was allowed to evaporate slowly and colorless columnar crystals of (MBZOX)·(1,3,5-F3I3B) were obtained after 1 d.
2.2.13. 3(MBZTH)·4(1,2-F4DIB)
2-mercaptobenzothiazole (21 mg, 0.126 mmol) and 1,2-diiodotetrafluorobenzene (103 mg, 0.256 mmol) were weighed into a 20 ml glass vial. Methanol (10 ml) was added and the mixture was stirred until a clear solution was obtained. The solvent was allowed to evaporate slowly and colorless plate-like crystals of 3(MBZTH)·4(1,2-F4DIB) were obtained after 3 d.
2.2.14. (MBZTH)·(1,3-F4DIB)
2-Mercaptobenzothiazole (24 mg, 0.143 mmol) and 1,3-diiodotetrafluorobenzene (50 mg, 0.124 mmol) were weighed into a 20 ml glass vial. Methanol (10 ml) was added and the mixture was stirred until a clear solution was obtained. The solvent was allowed to evaporate slowly and colorless plate-like crystals of (MBZTH)·(1,3-F4DIB) were obtained after 3 d.
2.2.15. (MBZTH)·2(1,3-F4DIB)
2-Mercaptobenzothiazole (22 mg, 0.132 mmol) and 1,3-diiodotetrafluorobenzene (98 mg, 0.244 mmol) were weighed into a 20 ml glass vial. Methanol (10 ml) was added and the mixture was stirred until a clear solution was obtained. The solvent was allowed to evaporate slowly and colorless tabular crystals of (MBZTH)·2(1,3-F4DIB) were obtained after 4 d.
2.2.16. 2(MBZTH)·(1,4-F4DIB)
2-Mercaptobenzothiazole (46 mg, 0.275 mmol) and 1,4-diiodotetrafluorobenzene (50 mg, 0.124 mmol) were weighed into a 20 ml glass vial. Acetone (10 ml) was added and the mixture was stirred until a clear solution was obtained. The solvent was allowed to evaporate slowly and colorless needle-like crystals of 2(MBZTH)·(1,4-F4DIB) were obtained after 2 d.
2.2.17. (MBZTH)·(1,3,5-F3I3B)
2-Mercaptobenzothiazole (32 mg, 0.191 mmol) and 1,3,5-trifluoro-2,4,6-triiodobenzene (50 mg, 0.098 mmol) were weighed into a 20 ml glass vial. Acetone (10 ml) was added and the mixture was stirred until a clear solution was obtained. The solvent was allowed to evaporate slowly and colorless tabular crystals of (MBZTH)·(1,3,5-F3I3B) were obtained after 2 d.
2.2.18. (MBZTH)·(TIE)
2-Mercaptobenzothiazole (33 mg, 0.197 mmol) and tetraiodoethylene (50 mg, 0.094 mmol) were weighed into a 20 ml glass vial. Methanol (15 ml) was added and the mixture was stirred with gentle heating until a clear solution was obtained. The solvent was allowed to evaporate slowly and colorless block-like crystals of (MBZTH)·(TIE) were obtained after 5 d.
2.3. Refinement
Crystal data, data collection and structure . H atoms on C atoms were calculated in idealized positions riding on their parent atoms, with C—H = 0.98 Å and Uiso(H) = 1.5Ueq(C) for methyl H atoms, and C—H = 0.95 Å and Uiso(H) = 1.2Ueq(C) for other H atoms. H atoms on heteroatoms were located in difference Fourier maps and refined isotropically, utilizing appropriate restraints [N—H = 0.86 (2) Å] where necessary to maintain chemically reasonable geometries. The H atoms of the water molecule in 2(MMBZIM)·(1,4-F4DIB)·2(H2O) were modeled in a disordered arrangement due to symmetry considerations.
details are summarized in Table 13. Results and discussion
3.1. Cocrystals of imidazolidine-2-thione (IT)
The smallest of the sulfur-containing compounds within this study, imidazolidine-2-thione, contains a thiourea functionality within a five-membered saturated ring. The first cocrystal formed with this compound in the present study is 2(IT)·(1,3-F4DIB), which was refined in the orthorhombic Pbcn with two unique molecules of IT and one molecule of 1,3-F4DIB in the (Fig. 2). As is common in thiourea-containing structures, a pair of N—H⋯S hydrogen bonds links thiourea molecules, in this case, into tetrameric units (Table 2) (Peloquin et al., 2021d, 2022). This is in contrast to the formation of hydrogen-bonded ribbons and discrete dimers, which are formed in the previously published 2(IT)·(1,2-F4DIB) and (IT)·2(1,2-F4DIB) cocrystals, respectively (Happonen et al., 2021). Tetrameric units align into staggered stacks in the b direction. These stacks are separated by additional tetrameric units, with the planes of the tetramers inclined by approximately 64°. This arrangement of inclined hydrogen-bonding units is also observed in the dimeric units of (IT)·(1,4-F4DIB) (Happonen et al., 2021). At the end of each tetramer, the remaining N—H hydrogen serves to link to the next inclined tetramer via N—H⋯S hydrogen bonding. The S atom at this end, S1, acts as a C—I⋯S halogen-bond acceptor to two different 1,3-F4DIB molecules (Table 3). These halogen-bonding interactions link adjacent stacks of tetramers in the c direction. The second IT-containing cocrystal of this study, (IT)·(1,3,5-F3I3B), was refined in the orthorhombic Pbca with one molecule each of IT and 1,3,5-F3I3B in the This structure represents the only example within this study without N—H⋯S hydrogen bonding (Table 4). Instead, C—I⋯S halogen bonding occurs between alternating molecules of IT and 1,3,5-F3I3B to form chains propagating in the c direction. The third I atom of 1,3,5-F3I3B, which does not participate in significant interactions with sulfur, instead serves to link chains in the ac plane via C—I⋯I halogen bonding.
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3.2. Cocrystals of 2-mercaptobenzimidazole (MBZIM)
Moving to the larger thiourea-containing molecule 2-mercaptobenzimidazole (MBZIM) yielded three new structures dominated by co-operative hydrogen and halogen bonding (Fig. 3). With 1,3-F4DIB, the cocrystalline structure of 4(MBZIM)·3(1,3-F4DIB) was obtained in the triclinic P, with four unique molecules of MBZIM and three molecules of 1,3-F4DIB in the In this structure, hydrogen bonding between thiourea molecules contributes to the formation of ribbons propagating along the a axis (Table 5). Two of the three 1,3-F4DIB molecules are pendants along these chains, linked via C—I⋯S. The second I atom of these particular 1,3-F4DIB molecules does not contribute to significant halogen- or chalcogen-bonding interactions. This hydrogen-bonding thiourea ribbon with halogen-bonding pendants is analogous to that observed in (MBZIM)·(1,2-F4DIB) (Arman et al., 2008, 2010). The final unique 1,3-F4DIB molecule lies between the ring planes of the pendant molecules of 1,3-F4DIB, contributing to only weak C—I⋯H, C—F⋯H, and C—F⋯F—C interactions. The combination of MBZIM and 1,4-F4DIB resulted in the (MBZIM)·(1,4-F4DIB) cocrystal, refined in the monoclinic P21/c, with one molecule each of both MBZIM and 1,4-F4DIB in the Just as in 4(MBZIM)·3(1,3-F4DIB), the structure of (MBZIM)·(1,4-F4DIB) consists of ribbons of MBZIM molecules propagating in the c direction, formed through thiourea hydrogen bonding (Table 6). Molecules of 1,4-F4DIB act as pendants along these ribbons, linked via C—I⋯S halogen bonding.
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With four I atoms available, tetraiodoethylene (TIE) often enables structural motifs that are different from the typical aromatic halogen-bond donors. The cocrystal (MBZIM)·(TIE) was refined in the orthorhombic Pnma, with one molecule each of MBZIM and TIE in the As in the previous examples, molecules of MBZIM form infinite ribbons through thiourea hydrogen bonding (Table 7). Three of the four I atoms of TIE function as C—I⋯S halogen-bond donor atoms to link these ribbons, creating a three-dimensional framework through the combination of hydrogen and halogen bonding. The fourth I atom participates in a C—I⋯π interaction [I⋯π = 3.351 (3) Å] to reinforce the framework.
3.3. Cocrystals of 2-mercapto-5-methylbenzimidazole (MMBZIM)
Adding a methyl group to MBZIM, resulting in 2-mercapto-5-methylbenzimidazole (MMBZIM), induces significant changes to the overall hydrogen- and halogen-bonding motifs. The structural literature of this substrate is limited, having only been characterized by single-crystal X-ray diffraction when acting as a ligand for transition metals coordinating through its S atom (Lin et al., 2017; Ozturk et al., 2009; Mitra et al., 2012). The first halogen-bonded cocrystal of MMBZIM in this study, (MMBZIM)·(1,2-F4DIB), was refined in the triclinic P, with one molecule each of MMBZIM and 1,2-F4DIB in the (Fig. 4). A discrete hydrogen-bonded dimer of two MMBZIM molecules is observed, in contrast to the infinite ribbons in (MBZIM)·(1,2-F4DIB) and most of the cocrystals in the present study (Table 8). Two molecules of 1,2-F4DIB per MMBZIM molecule link the dimers via C—I⋯S halogen bonds, leading to the formation of chains along the c axis.
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Isolated as a hydrated cocrystal from adventitious water, 2(MMBZIM)·(1,4-F4DIB)·2(H2O) crystallizes in the triclinic P with one molecule each of MMBZIM and H2O, as well as half a molecule of 1,4-F4DIB, in the All attempts to obtain an nonhydrated cocrystal with 1,4-F4DIB were unsuccessful, suggesting the packing arrangement formed strictly by halogen bonding contains small but meaningful voids that must be occupied by the water molecule. Discrete hydrogen-bonded dimers are again observed by hydrogen bonding of the thioamides (Table 9). Differing from (MMBZIM)·(1,2-F4DIB), with two halogen bonds to each S atom, 2(MMBZIM)·(1,4-F4DIB)·2(H2O) utilizes one C—I⋯S halogen bond and one O—H⋯S hydrogen bond at each S atom. It is the halogen bonding that contributes to the formation of infinite chains by linking the discrete dimers. The water molecule also acts as an N—H⋯O hydrogen-bond acceptor from the N atom that does not participate in thioamide hydrogen bonding and so is an intermediate linker facilitating the formation of an expanded thioamide ribbon motif.
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Finally, the combination of 1,3,5-F3I3B and MMBZIM resulted in the cocrystal (MMBZIM)·(1,3,5-F3I3B), refined in the monoclinic P21/c with one unique molecule of each component in the The overall packing motif in this structure is strikingly similar to that in (MMBZIM)·(1,2-F4DIB). Two molecules of MMBZIM form dimeric pairs through hydrogen bonding of the thioamides (Table 10). The remaining N—H hydrogens are involved in weak N—H⋯I hydrogen bonds [H⋯I = 3.02 (8) Å]. A pair of C—I⋯S halogen bonds occurs at each S atom, contributing to chains propagating in the a direction. The third I atom is oriented as a potential acceptor for a C—F⋯I interaction, though the interaction distance is very near the sum of the van der Waals radii and it is unclear if there is a significant attraction to this interaction. Given the similar motifs of (MMBZIM)·(1,3,5-F3I3B) to (MMBZIM)·(1,2-F4DIB), it may be that the C—F⋯I contact is merely coincident within the motif formed by the N—H⋯S and C—I⋯S interactions.
3.4. Cocrystals of 2-mercaptobenzoxazole (MBZOX)
While infinite ribbons commonly formed through hydrogen bonding of the thioureas in MBZIM, substituting one secondary N atom for an O atom in 2-mercaptobenzoxazole (MBZOX) allows for the study of the structural motifs when only dimers can form through hydrogen bonding (Fig. 5). The structural literature surrounding MBZOX is sparse, limited to three reports of it acting as a ligand through the S atom in transition-metal complexes (McFarlane et al., 1998; Nakahodo et al., 2000; Mitra et al., 2012) and its reaction with diiodine (Cristiani et al., 1995). Combined with 1,2-F4DIB, the cocrystalline structure of (MBZOX)·(1,2-F4DIB) was refined in the monoclinic P21/n, with one unique molecule each of MBZOX and 1,2-F4DIB in the Here, a hydrogen-bonding thioamide dimer is formed (Table 11), with each S atom acting as an acceptor to a single C—I⋯S halogen bond. The second I atom does not contribute to an additional halogen bond, instead being involved in a weak C—I⋯π interaction. This discrete four-molecule unit formed through hydrogen and halogen bonding stands in stark contrast to the infinite hydrogen-bonding ribbon with pendant halogen-bonded 1,2-F4DIB molecules observed in (MBZIM)·(1,2-F4DIB). The pattern of interactions in (MBZOX)·(1,3-F4DIB), which crystallizes in the monoclinic P21/c, with one molecule each of MBZOX and 1,3-F4DIB in the is more complex. Thioamide hydrogen-bonding dimers are once again observed (Table 12). These dimers stack along the b axis. Molecules of 1,3-F4DIB link neighboring stacks of dimers in the a direction. One of the I atoms serves as both a C—I⋯S halogen-bond donor and a C=S⋯I chalcogen-bond acceptor. The combination of halogen, chalcogen, and hydrogen-bonding results in the formation of a two-dimensional motif of intermolecular interactions. In 2(MBZOX)·(1,4-F4DIB), which was refined in the monoclinic C2/c, with one molecule of MBZOX and one-half of a molecule of 1,4-F4DIB, the packing motif is more reminiscent of its MMBZIM analogue. Thioamide hydrogen-bonding dimers are linked into chains through C—I⋯S halogen bonding (Table 13). The final example in the MBZOX series, (MBZOX)·(1,3,5-F3I3B), was refined in the monoclinic P21/c, with one molecule each of MBZOX and 1,3,5-F3I3B in the Much of the packing is similar to (MBZOX)·(1,3-F4DIB), with thioamide hydrogen-bonding dimers stacking in the b direction (Table 14). Neighboring stacks are linked along the a axis by both C—I⋯S halogen bonding and a C=S⋯I chalcogen bond to again form a two-dimensional In this instance though, the third I atom of 1,3,5-F3I3B acts as a C—I⋯I halogen-bond donor, further consolidating the packing in the c direction to form a three-dimensional framework. In all cases of these MBZOX cocrystals, hydrogen- and halogen-bonding preference is given toward the thione S atom as the acceptor rather than the O atom of the heterocycle.
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3.5. Cocrystals of 2-mercaptobenzothiazole (MBZTH)
As with MBZOX, 2-mercaptobenzothiazole lacks the thiourea functionality to allow for the formation of infinite ribbons through hydrogen bonding; however, the additional S atom can potentially act in either halogen- or chalcogen-bonding interactions (Fig. 6). Just as with MBZOX, the prior structural literature is dominated by examples of MBZTH acting as a ligand in transition-metal complexes (Aslanidis et al., 2002; Zhou et al., 2013b; Hadjikakou & Kubicki, 2000) or reactions with dihalides (Daga et al., 2002; Koskinen et al., 2015a,b). The first and most complex of the MBZTH structures obtained, 3(MBZTH)·4(1,2-F4DIB), crystallized in the triclinic P, with three molecules of MBZTH and four molecules of 1,2-F4DIB in the Thioamide dimers stack along the a axis (Table 15), with one molecule of 1,2-F4DIB within alternating layers. The remaining molecules of 1,2-F4DIB are oriented approximately perpendicular to the thioamide dimers, linking layers of the stack through a series of C—I⋯S halogen bonds. The intra-stack molecule of 1,2-F4DIB is also linked to a molecule of 1,2-F4DIB on the edge of the stack through a C—I⋯I halogen bond. This complex series of interactions ultimately forms a three-dimensional framework.
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The packing motif of (MBZTH)·(1,3-F4DIB), refined in the triclinic P, with one molecule each of MBZTH and 1,3-F4DIB within the is similar to that of (MMBZIM)·(1,2-F4DIB) and (MMBZIM)·(1,3,5-F3I3B). Thioamide hydrogen-bonding dimers (Table 16) are linked by a pair of unique C—I⋯S halogen bonds to the thione S atom, forming chains in the c direction. Crystallizing in the monoclinic P21, the of (MBZTH)·2(1,3-F4DIB) contains two unique molecules of MBZTH and four molecules of 1,3-F4DIB. In this case, the thioamide hydrogen-bonding dimers (Table 17) are linked by molecules of 1,3-F4DIB via C—I⋯S halogen bonding to form chains. These interactions occur to the thione and thiazole S atoms, with the interaction to the thione S atom occurring at a distance approximately 0.35 Å shorter than to the thiazole S atom. The remaining two molecules of 1,3-F4DIB are located as pendants along the chain, linked by C—I⋯I halogen bonding.
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The packing motif of 2(MBZTH)·(1,4-F4DIB), refined in the monoclinic P21/n, with one complete molecule of MBZTH and one-half of a molecule of 1,4-F4DIB in the is similar to that of 2(MBZOX)·(1,4-F4DIB). Thioamide hydrogen-bonding dimers (Table 18) are linked into chains via C—I⋯S halogen bonding to the thione S atom. As the final example with an aromatic halogen-bond donor, (MBZTH)·(1,3,5-F3I3B) was obtained in the monoclinic P21/c, with one unique molecule each of both MBZTH and 1,3,5-F3I3B in the The primary packing motif is similar to that of (MBZTH)·2(1,3-F4DIB), with the thioamide hydrogen-bonding dimers (Table 19) linked into chains by C—I⋯S halogen bonds to both the thione and thiazole S atoms. The third I atom serves to link neighboring chains through a weak C—I⋯S—C interaction to a thiazole S atom; however, the geometry of this interaction [C—I⋯S = 149.3 (1) and 142.48 (13)°] is indicative of a dispersive Type I interaction and not a true halogen or chalcogen bond. Finally, (MBZTH)·(TIE) crystallized in the triclinic P with one unique molecule of MBZTH and two unique half molecules of TIE in the Thioamide hydrogen-bonding dimers (Table 20) are linked into chains by C—I⋯S halogen bonding to the thione S atom. These chains are linked in the ab plane by additional C—I⋯S halogen bonding to the thione S atom. The second unique TIE molecule serves to consolidate the packing in the c direction via C—I⋯I halogen bonding, forming a three-dimensional framework.
|
|
4. Conclusion
A rich structural chemistry of cocrystals was observed between organoiodine molecules and heterocyclic thiones in the present study of 18 crystal structures. The structures are primarily directed by the co-operative effects of hydrogen- and halogen-bonding interactions. Certain features of the long-range structures were controlled through the selection of the heterocyclic thione, where the formation of primarily hydrogen-bonded ribbons in benzimidazoles could be truncated to hydrogen-bonded dimers in benzoxazoles and benzothiazoles. The hydrogen-bonded units were then aggregated into longer-range one- or two-dimensional motifs through C—I⋯S halogen bonding. Additional C—I⋯I halogen bonding, either through the stoichiometric excess of organoiodine or through the use of more iodine-rich organoiodine substrates (tetraiodoethylene, for example) extended some structures into three-dimensional frameworks. The RXB value for the majority of the halogen-bonding interactions lies within a typical range from 0.85 to 1.0. The interactions to a thione S atom generally occurred at shorter distances than the thiane S atom, as expected due to the state. The linearity parameter, ψ, ranges from 0.02 to 0.83. This wide range is supported by the distribution of electron density on S or I acceptor atoms. Occasional C=S⋯I chalcogen bonding was observed. Halogen-bond preference toward the thione S atom over the heterocyclic O or S atom was observed in both the benzoxazoles and benzothiazoles. However, there were at least some occasional occurrences of C—I⋯S to the thiazole S atom.
Supporting information
https://doi.org/10.1107/S2053229622009548/qw3002sup1.cif
contains datablocks 2IT_13F4DIB, IT_135F3I3B, 4MBZIM_313F4DIB, MBZIM_14F4DIB, MBZIM_TIE, MMBZIM_12F4DIB, 2MMBZIM_14F4DIB_2H2O, MMBZIM_135F3I3B, MBZOX_12F4DIB, MBZOX_13F4DIB, 2MBZOX_14F4DIB, MBZOX_135F3I3B, 3MBZTH_412F4DIB, MBZTH_13F4DIB, MBZTH_213F4DIB, 2MBZTH_14F4DIB, MBZTH_135F3I3B, MBZTH_TIE, global. DOI:Structure factors: contains datablock 2IT_13F4DIB. DOI: https://doi.org/10.1107/S2053229622009548/qw30022IT_13F4DIBsup2.hkl
Structure factors: contains datablock IT_135F3I3B. DOI: https://doi.org/10.1107/S2053229622009548/qw3002IT_135F3I3Bsup3.hkl
Structure factors: contains datablock 4MBZIM_313F4DIB. DOI: https://doi.org/10.1107/S2053229622009548/qw30024MBZIM_313F4DIBsup4.hkl
Structure factors: contains datablock MBZIM_14F4DIB. DOI: https://doi.org/10.1107/S2053229622009548/qw3002MBZIM_14F4DIBsup5.hkl
Structure factors: contains datablock MBZIM_TIE. DOI: https://doi.org/10.1107/S2053229622009548/qw3002MBZIM_TIEsup6.hkl
Structure factors: contains datablock MMBZIM_12F4DIB. DOI: https://doi.org/10.1107/S2053229622009548/qw3002MMBZIM_12F4DIBsup7.hkl
Structure factors: contains datablock 2MMBZIM_14F4DIB_2H2O. DOI: https://doi.org/10.1107/S2053229622009548/qw30022MMBZIM_14F4DIB_2H2Osup8.hkl
Structure factors: contains datablock MMBZIM_135F3I3B. DOI: https://doi.org/10.1107/S2053229622009548/qw3002MMBZIM_135F3I3Bsup9.hkl
Structure factors: contains datablock MBZOX_12F4DIB. DOI: https://doi.org/10.1107/S2053229622009548/qw3002MBZOX_12F4DIBsup10.hkl
Structure factors: contains datablock MBZOX_13F4DIB. DOI: https://doi.org/10.1107/S2053229622009548/qw3002MBZOX_13F4DIBsup11.hkl
Structure factors: contains datablock 2MBZOX_14F4DIB. DOI: https://doi.org/10.1107/S2053229622009548/qw30022MBZOX_14F4DIBsup12.hkl
Structure factors: contains datablock MBZOX_135F3I3B. DOI: https://doi.org/10.1107/S2053229622009548/qw3002MBZOX_135F3I3Bsup13.hkl
Structure factors: contains datablock 3MBZTH_412F4DIB. DOI: https://doi.org/10.1107/S2053229622009548/qw30023MBZTH_412F4DIBsup14.hkl
Structure factors: contains datablock MBZTH_13F4DIB. DOI: https://doi.org/10.1107/S2053229622009548/qw3002MBZTH_13F4DIBsup15.hkl
Structure factors: contains datablock MBZTH_213F4DIB. DOI: https://doi.org/10.1107/S2053229622009548/qw3002MBZTH_213F4DIBsup16.hkl
Structure factors: contains datablock 2MBZTH_14F4DIB. DOI: https://doi.org/10.1107/S2053229622009548/qw30022MBZTH_14F4DIBsup17.hkl
Structure factors: contains datablock MBZTH_135F3I3B. DOI: https://doi.org/10.1107/S2053229622009548/qw3002MBZTH_135F3I3Bsup18.hkl
Structure factors: contains datablock MBZTH_TIE. DOI: https://doi.org/10.1107/S2053229622009548/qw3002MBZTH_TIEsup19.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2053229622009548/qw30022IT_13F4DIBsup20.cml
Supporting information file. DOI: https://doi.org/10.1107/S2053229622009548/qw3002IT_135F3I3Bsup21.cml
Supporting information file. DOI: https://doi.org/10.1107/S2053229622009548/qw30024MBZIM_313F4DIBsup22.cml
Supporting information file. DOI: https://doi.org/10.1107/S2053229622009548/qw3002MBZIM_14F4DIBsup23.cml
Supporting information file. DOI: https://doi.org/10.1107/S2053229622009548/qw3002MBZIM_TIEsup24.cml
Supporting information file. DOI: https://doi.org/10.1107/S2053229622009548/qw3002MMBZIM_12F4DIBsup25.cml
Supporting information file. DOI: https://doi.org/10.1107/S2053229622009548/qw30022MMBZIM_14F4DIB_2H2Osup26.cml
Supporting information file. DOI: https://doi.org/10.1107/S2053229622009548/qw3002MMBZIM_135F3I3Bsup27.cml
Supporting information file. DOI: https://doi.org/10.1107/S2053229622009548/qw3002MBZOX_12F4DIBsup28.cml
Supporting information file. DOI: https://doi.org/10.1107/S2053229622009548/qw3002MBZOX_13F4DIBsup29.cml
Supporting information file. DOI: https://doi.org/10.1107/S2053229622009548/qw30022MBZOX_14F4DIBsup30.cml
Supporting information file. DOI: https://doi.org/10.1107/S2053229622009548/qw3002MBZOX_135F3I3Bsup31.cml
Supporting information file. DOI: https://doi.org/10.1107/S2053229622009548/qw30023MBZTH_412F4DIBsup32.cml
Supporting information file. DOI: https://doi.org/10.1107/S2053229622009548/qw3002MBZTH_13F4DIBsup33.cml
Supporting information file. DOI: https://doi.org/10.1107/S2053229622009548/qw3002MBZTH_213F4DIBsup34.cml
Supporting information file. DOI: https://doi.org/10.1107/S2053229622009548/qw30022MBZTH_14F4DIBsup35.cml
Supporting information file. DOI: https://doi.org/10.1107/S2053229622009548/qw3002MBZTH_135F3I3Bsup36.cml
Supporting information file. DOI: https://doi.org/10.1107/S2053229622009548/qw3002MBZTH_TIEsup37.cml
For all structures, data collection: APEX3 (Bruker, 2017); cell
SAINT (Bruker, 2017); data reduction: SAINT (Bruker, 2017); program(s) used to solve structure: SHELXT2018 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b). Molecular graphics: Mercury (Macrae et al., 2020) for 2IT_13F4DIB, 4MBZIM_313F4DIB, MBZIM_14F4DIB, MBZIM_TIE, MMBZIM_12F4DIB, 2MMBZIM_14F4DIB_2H2O, MMBZIM_135F3I3B, MBZOX_12F4DIB, MBZOX_13F4DIB, 2MBZOX_14F4DIB, MBZOX_135F3I3B, 3MBZTH_412F4DIB, MBZTH_13F4DIB, MBZTH_213F4DIB, 2MBZTH_14F4DIB, MBZTH_135F3I3B, MBZTH_TIE; OLEX2 (Dolomanov et al., 2009) for IT_135F3I3B. For all structures, software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).C6F4I2·2C3H6N2S | Dx = 2.193 Mg m−3 |
Mr = 606.18 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbcn | Cell parameters from 9343 reflections |
a = 15.6704 (7) Å | θ = 2.6–30.1° |
b = 8.9924 (4) Å | µ = 3.69 mm−1 |
c = 26.0573 (10) Å | T = 100 K |
V = 3671.9 (3) Å3 | Block, colourless |
Z = 8 | 0.18 × 0.17 × 0.13 mm |
F(000) = 2288 |
Bruker D8 Venture Photon 2 diffractometer | 5198 reflections with I > 2σ(I) |
Radiation source: Incoatec IµS | Rint = 0.035 |
φ and ω scans | θmax = 30.1°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2017) | h = −22→22 |
Tmin = 0.639, Tmax = 0.746 | k = −12→12 |
112821 measured reflections | l = −36→31 |
5376 independent reflections |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.015 | w = 1/[σ2(Fo2) + (0.0054P)2 + 3.3158P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.032 | (Δ/σ)max = 0.003 |
S = 1.25 | Δρmax = 0.42 e Å−3 |
5376 reflections | Δρmin = −0.36 e Å−3 |
234 parameters | Extinction correction: SHELXL2018 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.00082 (4) |
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 | 0.71842 (2) | 0.27502 (2) | 0.20785 (2) | 0.01326 (3) | |
I2 | 0.98485 (2) | 0.54110 (2) | 0.35028 (2) | 0.01761 (3) | |
F1 | 0.89456 (6) | 0.34626 (11) | 0.26335 (4) | 0.01975 (19) | |
F2 | 0.81145 (7) | 0.69420 (11) | 0.38910 (4) | 0.0230 (2) | |
F3 | 0.64754 (6) | 0.66108 (12) | 0.36116 (4) | 0.0232 (2) | |
F4 | 0.60595 (6) | 0.48196 (12) | 0.28175 (4) | 0.0215 (2) | |
C7 | 0.74984 (10) | 0.40891 (16) | 0.27097 (5) | 0.0139 (3) | |
C8 | 0.83358 (10) | 0.42536 (17) | 0.28725 (6) | 0.0145 (3) | |
C9 | 0.85758 (10) | 0.51990 (17) | 0.32680 (6) | 0.0157 (3) | |
C10 | 0.79313 (10) | 0.59875 (17) | 0.35087 (6) | 0.0165 (3) | |
C11 | 0.70856 (10) | 0.58350 (18) | 0.33669 (6) | 0.0172 (3) | |
C12 | 0.68786 (10) | 0.49038 (18) | 0.29640 (6) | 0.0155 (3) | |
S1 | 0.68567 (2) | 0.95036 (4) | 0.61354 (2) | 0.01476 (7) | |
N1 | 0.69251 (9) | 0.72075 (15) | 0.54616 (5) | 0.0166 (3) | |
HN1 | 0.7189 (14) | 0.672 (3) | 0.5672 (9) | 0.027 (6)* | |
N2 | 0.64832 (10) | 0.92951 (15) | 0.51306 (5) | 0.0182 (3) | |
HN2 | 0.6289 (14) | 1.015 (2) | 0.5136 (8) | 0.022 (5)* | |
C1 | 0.67475 (9) | 0.86294 (17) | 0.55568 (6) | 0.0134 (3) | |
C2 | 0.68382 (11) | 0.68448 (18) | 0.49167 (6) | 0.0186 (3) | |
H2A | 0.644157 | 0.600134 | 0.486460 | 0.022* | |
H2B | 0.739772 | 0.659716 | 0.476228 | 0.022* | |
C3 | 0.64743 (11) | 0.82909 (18) | 0.46895 (6) | 0.0199 (3) | |
H3A | 0.683895 | 0.867131 | 0.440842 | 0.024* | |
H3B | 0.588726 | 0.814231 | 0.455882 | 0.024* | |
S2 | 0.42217 (3) | 0.71986 (5) | 0.49680 (2) | 0.02184 (9) | |
N3 | 0.47631 (10) | 0.51791 (16) | 0.42741 (5) | 0.0199 (3) | |
HN3 | 0.4952 (13) | 0.467 (2) | 0.4491 (9) | 0.020 (5)* | |
N4 | 0.40214 (9) | 0.69778 (16) | 0.39417 (5) | 0.0173 (3) | |
HN4 | 0.3816 (15) | 0.783 (3) | 0.3921 (9) | 0.028 (6)* | |
C4 | 0.43369 (10) | 0.64323 (17) | 0.43758 (6) | 0.0150 (3) | |
C5 | 0.46475 (10) | 0.47080 (17) | 0.37446 (6) | 0.0166 (3) | |
H5A | 0.423029 | 0.388469 | 0.371861 | 0.020* | |
H5B | 0.519445 | 0.439328 | 0.358855 | 0.020* | |
C6 | 0.43059 (11) | 0.61337 (18) | 0.34929 (6) | 0.0180 (3) | |
H6A | 0.476022 | 0.666661 | 0.330344 | 0.022* | |
H6B | 0.382641 | 0.591836 | 0.325695 | 0.022* |
U11 | U22 | U33 | U12 | U13 | U23 | |
I1 | 0.01584 (5) | 0.01297 (5) | 0.01098 (4) | −0.00009 (3) | −0.00092 (3) | 0.00036 (3) |
I2 | 0.01801 (5) | 0.01630 (5) | 0.01853 (5) | −0.00213 (4) | −0.00276 (4) | −0.00185 (4) |
F1 | 0.0169 (4) | 0.0213 (5) | 0.0210 (5) | 0.0041 (4) | 0.0008 (4) | −0.0073 (4) |
F2 | 0.0276 (5) | 0.0234 (5) | 0.0182 (5) | −0.0016 (4) | 0.0000 (4) | −0.0098 (4) |
F3 | 0.0216 (5) | 0.0265 (5) | 0.0215 (5) | 0.0042 (4) | 0.0058 (4) | −0.0079 (4) |
F4 | 0.0143 (4) | 0.0284 (5) | 0.0217 (5) | 0.0006 (4) | 0.0006 (4) | −0.0042 (4) |
C7 | 0.0190 (7) | 0.0121 (6) | 0.0105 (6) | −0.0010 (5) | 0.0006 (5) | 0.0002 (5) |
C8 | 0.0170 (7) | 0.0124 (6) | 0.0141 (6) | 0.0019 (5) | 0.0012 (5) | −0.0001 (5) |
C9 | 0.0175 (7) | 0.0140 (7) | 0.0155 (7) | −0.0009 (5) | −0.0013 (5) | 0.0000 (5) |
C10 | 0.0222 (8) | 0.0144 (7) | 0.0128 (6) | −0.0015 (6) | 0.0005 (6) | −0.0015 (5) |
C11 | 0.0205 (7) | 0.0159 (7) | 0.0152 (7) | 0.0022 (6) | 0.0043 (6) | −0.0010 (6) |
C12 | 0.0150 (7) | 0.0167 (7) | 0.0146 (6) | −0.0010 (6) | 0.0007 (5) | 0.0014 (5) |
S1 | 0.01883 (17) | 0.01408 (16) | 0.01138 (15) | 0.00309 (13) | −0.00079 (13) | 0.00015 (13) |
N1 | 0.0220 (7) | 0.0127 (6) | 0.0150 (6) | 0.0032 (5) | −0.0018 (5) | 0.0014 (5) |
N2 | 0.0277 (7) | 0.0133 (6) | 0.0136 (6) | 0.0055 (5) | −0.0030 (5) | −0.0008 (5) |
C1 | 0.0119 (6) | 0.0140 (6) | 0.0142 (6) | 0.0004 (5) | 0.0011 (5) | 0.0008 (5) |
C2 | 0.0259 (8) | 0.0148 (7) | 0.0152 (7) | 0.0014 (6) | 0.0001 (6) | −0.0028 (6) |
C3 | 0.0276 (8) | 0.0180 (7) | 0.0141 (7) | 0.0030 (6) | −0.0023 (6) | −0.0026 (6) |
S2 | 0.0339 (2) | 0.01651 (18) | 0.01508 (17) | 0.01055 (16) | −0.00313 (16) | −0.00093 (14) |
N3 | 0.0280 (7) | 0.0164 (6) | 0.0151 (6) | 0.0094 (6) | −0.0051 (5) | 0.0000 (5) |
N4 | 0.0212 (7) | 0.0146 (6) | 0.0161 (6) | 0.0054 (5) | −0.0028 (5) | 0.0010 (5) |
C4 | 0.0143 (7) | 0.0127 (6) | 0.0179 (7) | 0.0004 (5) | −0.0011 (5) | 0.0015 (5) |
C5 | 0.0197 (7) | 0.0139 (7) | 0.0161 (7) | 0.0018 (6) | 0.0003 (6) | −0.0003 (5) |
C6 | 0.0221 (8) | 0.0167 (7) | 0.0153 (7) | 0.0043 (6) | −0.0022 (6) | 0.0002 (6) |
I1—C7 | 2.0969 (14) | N2—C3 | 1.462 (2) |
I2—C9 | 2.0947 (16) | C2—H2A | 0.9900 |
F1—C8 | 1.3442 (17) | C2—H2B | 0.9900 |
F2—C10 | 1.3459 (17) | C2—C3 | 1.538 (2) |
F3—C11 | 1.3445 (18) | C3—H3A | 0.9900 |
F4—C12 | 1.3412 (18) | C3—H3B | 0.9900 |
C7—C8 | 1.387 (2) | S2—C4 | 1.6995 (16) |
C7—C12 | 1.385 (2) | N3—HN3 | 0.79 (2) |
C8—C9 | 1.388 (2) | N3—C4 | 1.337 (2) |
C9—C10 | 1.384 (2) | N3—C5 | 1.455 (2) |
C10—C11 | 1.383 (2) | N4—HN4 | 0.83 (2) |
C11—C12 | 1.382 (2) | N4—C4 | 1.328 (2) |
S1—C1 | 1.7088 (15) | N4—C6 | 1.464 (2) |
N1—HN1 | 0.81 (2) | C5—H5A | 0.9900 |
N1—C1 | 1.332 (2) | C5—H5B | 0.9900 |
N1—C2 | 1.463 (2) | C5—C6 | 1.536 (2) |
N2—HN2 | 0.83 (2) | C6—H6A | 0.9900 |
N2—C1 | 1.3280 (19) | C6—H6B | 0.9900 |
C8—C7—I1 | 121.56 (11) | H2A—C2—H2B | 109.1 |
C12—C7—I1 | 120.94 (11) | C3—C2—H2A | 111.2 |
C12—C7—C8 | 117.43 (14) | C3—C2—H2B | 111.2 |
F1—C8—C7 | 118.31 (13) | N2—C3—C2 | 102.49 (12) |
F1—C8—C9 | 118.39 (14) | N2—C3—H3A | 111.3 |
C7—C8—C9 | 123.29 (14) | N2—C3—H3B | 111.3 |
C8—C9—I2 | 122.05 (11) | C2—C3—H3A | 111.3 |
C10—C9—I2 | 121.04 (11) | C2—C3—H3B | 111.3 |
C10—C9—C8 | 116.90 (14) | H3A—C3—H3B | 109.2 |
F2—C10—C9 | 120.43 (14) | C4—N3—HN3 | 122.5 (16) |
F2—C10—C11 | 117.74 (14) | C4—N3—C5 | 111.80 (13) |
C11—C10—C9 | 121.83 (14) | C5—N3—HN3 | 124.0 (16) |
F3—C11—C10 | 120.23 (14) | C4—N4—HN4 | 122.7 (16) |
F3—C11—C12 | 120.52 (15) | C4—N4—C6 | 112.06 (13) |
C12—C11—C10 | 119.23 (14) | C6—N4—HN4 | 122.8 (16) |
F4—C12—C7 | 120.34 (14) | N3—C4—S2 | 125.10 (12) |
F4—C12—C11 | 118.37 (14) | N4—C4—S2 | 125.73 (12) |
C11—C12—C7 | 121.29 (15) | N4—C4—N3 | 109.17 (14) |
C1—N1—HN1 | 119.7 (16) | N3—C5—H5A | 111.4 |
C1—N1—C2 | 112.04 (13) | N3—C5—H5B | 111.4 |
C2—N1—HN1 | 125.6 (16) | N3—C5—C6 | 101.85 (12) |
C1—N2—HN2 | 121.3 (15) | H5A—C5—H5B | 109.3 |
C1—N2—C3 | 112.46 (13) | C6—C5—H5A | 111.4 |
C3—N2—HN2 | 125.8 (15) | C6—C5—H5B | 111.4 |
N1—C1—S1 | 125.81 (12) | N4—C6—C5 | 101.41 (12) |
N2—C1—S1 | 124.18 (12) | N4—C6—H6A | 111.5 |
N2—C1—N1 | 110.01 (14) | N4—C6—H6B | 111.5 |
N1—C2—H2A | 111.2 | C5—C6—H6A | 111.5 |
N1—C2—H2B | 111.2 | C5—C6—H6B | 111.5 |
N1—C2—C3 | 102.68 (12) | H6A—C6—H6B | 109.3 |
I1—C7—C8—F1 | −3.75 (19) | C9—C10—C11—C12 | −1.9 (2) |
I1—C7—C8—C9 | 175.92 (12) | C10—C11—C12—F4 | −177.15 (14) |
I1—C7—C12—F4 | 1.7 (2) | C10—C11—C12—C7 | 1.9 (2) |
I1—C7—C12—C11 | −177.34 (12) | C12—C7—C8—F1 | 179.43 (13) |
I2—C9—C10—F2 | 1.9 (2) | C12—C7—C8—C9 | −0.9 (2) |
I2—C9—C10—C11 | −178.45 (12) | N1—C2—C3—N2 | 4.94 (17) |
F1—C8—C9—I2 | −0.4 (2) | C1—N1—C2—C3 | −5.82 (18) |
F1—C8—C9—C10 | −179.48 (14) | C1—N2—C3—C2 | −2.96 (19) |
F2—C10—C11—F3 | −0.8 (2) | C2—N1—C1—S1 | −174.62 (12) |
F2—C10—C11—C12 | 177.76 (14) | C2—N1—C1—N2 | 4.27 (19) |
F3—C11—C12—F4 | 1.4 (2) | C3—N2—C1—S1 | 178.31 (12) |
F3—C11—C12—C7 | −179.58 (14) | C3—N2—C1—N1 | −0.6 (2) |
C7—C8—C9—I2 | 179.89 (11) | N3—C5—C6—N4 | −18.18 (16) |
C7—C8—C9—C10 | 0.9 (2) | C4—N3—C5—C6 | 16.94 (18) |
C8—C7—C12—F4 | 178.51 (14) | C4—N4—C6—C5 | 15.47 (18) |
C8—C7—C12—C11 | −0.5 (2) | C5—N3—C4—S2 | 172.13 (12) |
C8—C9—C10—F2 | −179.09 (14) | C5—N3—C4—N4 | −7.96 (19) |
C8—C9—C10—C11 | 0.6 (2) | C6—N4—C4—S2 | 174.32 (12) |
C9—C10—C11—F3 | 179.53 (14) | C6—N4—C4—N3 | −5.59 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—HN1···S1i | 0.81 (2) | 2.77 (2) | 3.5551 (14) | 163 (2) |
N2—HN2···S2ii | 0.83 (2) | 2.53 (2) | 3.3507 (14) | 172 (2) |
C2—H2B···F2 | 0.99 | 2.55 | 3.3392 (19) | 136 |
C3—H3B···S2 | 0.99 | 2.94 | 3.7351 (19) | 138 |
N3—HN3···S2iii | 0.79 (2) | 2.54 (2) | 3.3171 (15) | 167 (2) |
N4—HN4···I2iv | 0.83 (2) | 3.31 (2) | 3.7383 (14) | 114.9 (18) |
N4—HN4···S1ii | 0.83 (2) | 2.63 (2) | 3.4562 (14) | 179 (2) |
C5—H5A···I1v | 0.99 | 3.20 | 3.9922 (16) | 138 |
C5—H5B···F4 | 0.99 | 2.45 | 3.2774 (19) | 140 |
C6—H6B···I1vi | 0.99 | 3.18 | 3.9223 (16) | 133 |
Symmetry codes: (i) −x+3/2, y−1/2, z; (ii) −x+1, −y+2, −z+1; (iii) −x+1, −y+1, −z+1; (iv) −x+3/2, y+1/2, z; (v) −x+1, y, −z+1/2; (vi) x−1/2, y+1/2, −z+1/2. |
C6F3I3·C3H6N2S | Dx = 2.797 Mg m−3 |
Mr = 611.92 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbca | Cell parameters from 9914 reflections |
a = 18.0407 (14) Å | θ = 2.9–28.3° |
b = 7.2816 (6) Å | µ = 6.61 mm−1 |
c = 22.1250 (19) Å | T = 100 K |
V = 2906.5 (4) Å3 | Tabular, colourless |
Z = 8 | 0.22 × 0.08 × 0.04 mm |
F(000) = 2208 |
Bruker D8 Venture Photon 2 diffractometer | 3220 reflections with I > 2σ(I) |
Radiation source: Incoatec IµS | Rint = 0.043 |
φ and ω scans | θmax = 28.3°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2017) | h = −24→24 |
Tmin = 0.563, Tmax = 0.746 | k = −9→9 |
49179 measured reflections | l = −28→29 |
3615 independent reflections |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.019 | w = 1/[σ2(Fo2) + (0.0114P)2 + 5.9439P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.040 | (Δ/σ)max = 0.002 |
S = 1.11 | Δρmax = 0.57 e Å−3 |
3615 reflections | Δρmin = −0.77 e Å−3 |
172 parameters | Extinction correction: SHELXL2018 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
2 restraints | Extinction coefficient: 0.000108 (15) |
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 | 0.53750 (2) | 0.23369 (3) | 0.54191 (2) | 0.01895 (5) | |
I2 | 0.82382 (2) | 0.16514 (2) | 0.68496 (2) | 0.01507 (5) | |
I3 | 0.83267 (2) | 0.32805 (2) | 0.41594 (2) | 0.01451 (5) | |
F1 | 0.65074 (9) | 0.1654 (2) | 0.64879 (8) | 0.0189 (4) | |
F2 | 0.88045 (8) | 0.2474 (2) | 0.55242 (8) | 0.0197 (4) | |
F3 | 0.65981 (9) | 0.3180 (2) | 0.44277 (8) | 0.0179 (3) | |
C4 | 0.65271 (14) | 0.2418 (4) | 0.54544 (13) | 0.0139 (5) | |
C5 | 0.69034 (15) | 0.2057 (4) | 0.59879 (13) | 0.0146 (5) | |
C6 | 0.76726 (14) | 0.2079 (4) | 0.60287 (13) | 0.0135 (5) | |
C7 | 0.80537 (14) | 0.2449 (4) | 0.54993 (13) | 0.0140 (5) | |
C8 | 0.77196 (14) | 0.2814 (4) | 0.49545 (13) | 0.0133 (5) | |
C9 | 0.69470 (14) | 0.2803 (4) | 0.49494 (13) | 0.0137 (5) | |
S1 | 0.57097 (4) | 0.61400 (10) | 0.79736 (3) | 0.01671 (14) | |
N1 | 0.52694 (14) | 0.2877 (4) | 0.84174 (13) | 0.0228 (6) | |
HN1 | 0.4953 (19) | 0.345 (6) | 0.8617 (18) | 0.057 (14)* | |
N2 | 0.62179 (16) | 0.2684 (4) | 0.78288 (13) | 0.0257 (6) | |
HN2 | 0.6527 (16) | 0.308 (5) | 0.7585 (14) | 0.029 (10)* | |
C1 | 0.57324 (15) | 0.3832 (4) | 0.80740 (12) | 0.0161 (6) | |
C2 | 0.54227 (16) | 0.0908 (4) | 0.84203 (14) | 0.0222 (6) | |
H2A | 0.498578 | 0.019283 | 0.828618 | 0.027* | |
H2B | 0.557562 | 0.048198 | 0.882651 | 0.027* | |
C3 | 0.60613 (19) | 0.0758 (4) | 0.79654 (16) | 0.0277 (7) | |
H3A | 0.649751 | 0.014419 | 0.814660 | 0.033* | |
H3B | 0.590783 | 0.007958 | 0.759844 | 0.033* |
U11 | U22 | U33 | U12 | U13 | U23 | |
I1 | 0.01058 (8) | 0.02130 (10) | 0.02496 (11) | 0.00013 (7) | 0.00038 (7) | −0.00336 (8) |
I2 | 0.01700 (9) | 0.01397 (9) | 0.01424 (10) | −0.00039 (6) | −0.00190 (7) | 0.00115 (7) |
I3 | 0.01480 (8) | 0.01468 (9) | 0.01405 (9) | 0.00001 (6) | 0.00204 (7) | 0.00044 (7) |
F1 | 0.0176 (8) | 0.0235 (9) | 0.0157 (9) | −0.0029 (7) | 0.0045 (7) | 0.0016 (7) |
F2 | 0.0101 (7) | 0.0284 (10) | 0.0205 (9) | −0.0005 (6) | −0.0003 (6) | 0.0023 (8) |
F3 | 0.0170 (7) | 0.0204 (9) | 0.0163 (9) | 0.0018 (7) | −0.0034 (6) | 0.0024 (7) |
C4 | 0.0098 (11) | 0.0127 (13) | 0.0193 (14) | −0.0006 (10) | −0.0004 (10) | −0.0018 (11) |
C5 | 0.0172 (12) | 0.0111 (13) | 0.0155 (14) | −0.0027 (10) | 0.0038 (11) | −0.0007 (11) |
C6 | 0.0161 (12) | 0.0118 (13) | 0.0124 (13) | 0.0014 (10) | −0.0043 (10) | −0.0012 (10) |
C7 | 0.0118 (11) | 0.0110 (13) | 0.0191 (15) | 0.0014 (10) | −0.0010 (10) | 0.0000 (11) |
C8 | 0.0141 (12) | 0.0111 (13) | 0.0148 (14) | 0.0003 (10) | 0.0033 (10) | −0.0016 (11) |
C9 | 0.0137 (12) | 0.0120 (13) | 0.0153 (14) | 0.0024 (10) | −0.0036 (10) | −0.0001 (11) |
S1 | 0.0211 (3) | 0.0144 (3) | 0.0146 (3) | 0.0003 (3) | 0.0002 (3) | 0.0002 (3) |
N1 | 0.0236 (13) | 0.0181 (13) | 0.0267 (15) | −0.0027 (10) | 0.0051 (11) | 0.0020 (11) |
N2 | 0.0321 (14) | 0.0158 (13) | 0.0292 (16) | 0.0020 (11) | 0.0127 (12) | 0.0046 (12) |
C1 | 0.0168 (13) | 0.0223 (15) | 0.0092 (14) | −0.0006 (11) | −0.0037 (10) | −0.0001 (11) |
C2 | 0.0244 (14) | 0.0209 (15) | 0.0213 (16) | −0.0062 (12) | −0.0049 (12) | 0.0046 (13) |
C3 | 0.0397 (18) | 0.0155 (15) | 0.0278 (18) | 0.0006 (14) | 0.0044 (15) | 0.0037 (13) |
I1—C4 | 2.081 (2) | S1—C1 | 1.696 (3) |
I2—C6 | 2.106 (3) | N1—HN1 | 0.831 (19) |
I3—C8 | 2.100 (3) | N1—C1 | 1.326 (4) |
F1—C5 | 1.349 (3) | N1—C2 | 1.460 (4) |
F2—C7 | 1.356 (3) | N2—HN2 | 0.827 (18) |
F3—C9 | 1.343 (3) | N2—C1 | 1.327 (4) |
C4—C5 | 1.387 (4) | N2—C3 | 1.462 (4) |
C4—C9 | 1.379 (4) | C2—H2A | 0.9900 |
C5—C6 | 1.391 (4) | C2—H2B | 0.9900 |
C6—C7 | 1.385 (4) | C2—C3 | 1.534 (4) |
C7—C8 | 1.374 (4) | C3—H3A | 0.9900 |
C8—C9 | 1.394 (4) | C3—H3B | 0.9900 |
C5—C4—I1 | 121.0 (2) | C2—N1—HN1 | 128 (3) |
C9—C4—I1 | 121.6 (2) | C1—N2—HN2 | 119 (3) |
C9—C4—C5 | 117.4 (2) | C1—N2—C3 | 113.1 (3) |
F1—C5—C4 | 118.7 (2) | C3—N2—HN2 | 127 (3) |
F1—C5—C6 | 118.5 (3) | N1—C1—S1 | 125.4 (2) |
C4—C5—C6 | 122.8 (3) | N1—C1—N2 | 108.7 (3) |
C5—C6—I2 | 122.5 (2) | N2—C1—S1 | 125.9 (2) |
C7—C6—I2 | 121.18 (19) | N1—C2—H2A | 111.4 |
C7—C6—C5 | 116.3 (2) | N1—C2—H2B | 111.4 |
F2—C7—C6 | 117.7 (2) | N1—C2—C3 | 102.1 (2) |
F2—C7—C8 | 118.1 (2) | H2A—C2—H2B | 109.2 |
C8—C7—C6 | 124.2 (2) | C3—C2—H2A | 111.4 |
C7—C8—I3 | 122.51 (19) | C3—C2—H2B | 111.4 |
C7—C8—C9 | 116.4 (3) | N2—C3—C2 | 102.3 (3) |
C9—C8—I3 | 121.0 (2) | N2—C3—H3A | 111.3 |
F3—C9—C4 | 118.7 (2) | N2—C3—H3B | 111.3 |
F3—C9—C8 | 118.3 (2) | C2—C3—H3A | 111.3 |
C4—C9—C8 | 122.9 (3) | C2—C3—H3B | 111.3 |
C1—N1—HN1 | 118 (3) | H3A—C3—H3B | 109.2 |
C1—N1—C2 | 113.5 (3) | ||
I1—C4—C5—F1 | −0.2 (3) | C5—C6—C7—F2 | −179.8 (2) |
I1—C4—C5—C6 | 179.3 (2) | C5—C6—C7—C8 | 1.1 (4) |
I1—C4—C9—F3 | 1.7 (4) | C6—C7—C8—I3 | −177.9 (2) |
I1—C4—C9—C8 | −178.1 (2) | C6—C7—C8—C9 | 0.1 (4) |
I2—C6—C7—F2 | 1.9 (3) | C7—C8—C9—F3 | 179.0 (2) |
I2—C6—C7—C8 | −177.3 (2) | C7—C8—C9—C4 | −1.2 (4) |
I3—C8—C9—F3 | −2.9 (3) | C9—C4—C5—F1 | −179.2 (2) |
I3—C8—C9—C4 | 176.8 (2) | C9—C4—C5—C6 | 0.2 (4) |
F1—C5—C6—I2 | −3.4 (4) | N1—C2—C3—N2 | 5.8 (3) |
F1—C5—C6—C7 | 178.2 (2) | C1—N1—C2—C3 | −3.7 (3) |
F2—C7—C8—I3 | 2.9 (4) | C1—N2—C3—C2 | −6.8 (4) |
F2—C7—C8—C9 | −179.1 (2) | C2—N1—C1—S1 | −179.8 (2) |
C4—C5—C6—I2 | 177.1 (2) | C2—N1—C1—N2 | −0.4 (4) |
C4—C5—C6—C7 | −1.2 (4) | C3—N2—C1—S1 | −175.8 (2) |
C5—C4—C9—F3 | −179.2 (2) | C3—N2—C1—N1 | 4.8 (4) |
C5—C4—C9—C8 | 1.0 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—HN2···I2i | 0.83 (2) | 3.10 (3) | 3.742 (3) | 137 (3) |
C2—H2B···I1ii | 0.99 | 3.31 | 3.927 (3) | 122 |
C2—H2B···F3iii | 0.99 | 2.47 | 3.147 (3) | 125 |
Symmetry codes: (i) −x+3/2, y+1/2, z; (ii) −x+1, y−1/2, −z+3/2; (iii) x, −y+1/2, z+1/2. |
3C6F4I2·4C7H6N2S | Z = 2 |
Mr = 1806.37 | F(000) = 1692 |
Triclinic, P1 | Dx = 2.238 Mg m−3 |
a = 8.4573 (14) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 17.725 (3) Å | Cell parameters from 9879 reflections |
c = 18.759 (4) Å | θ = 2.4–27.5° |
α = 106.997 (7)° | µ = 3.72 mm−1 |
β = 93.229 (7)° | T = 100 K |
γ = 92.034 (7)° | Needle, colourless |
V = 2680.9 (9) Å3 | 0.34 × 0.04 × 0.04 mm |
Bruker D8 Venture Photon 2 diffractometer | 10558 reflections with I > 2σ(I) |
Radiation source: Incoatec IµS | Rint = 0.056 |
φ and ω scans | θmax = 27.6°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2017) | h = −10→10 |
Tmin = 0.668, Tmax = 0.746 | k = −23→23 |
118524 measured reflections | l = −24→24 |
12297 independent reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.021 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.041 | w = 1/[σ2(Fo2) + (0.0068P)2 + 2.3276P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.002 |
12297 reflections | Δρmax = 0.52 e Å−3 |
717 parameters | Δρmin = −0.75 e Å−3 |
8 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 | 0.23723 (2) | 0.28696 (2) | 0.64287 (2) | 0.01892 (4) | |
I2 | 0.11203 (2) | 0.62311 (2) | 0.81696 (2) | 0.02185 (4) | |
F29 | 0.12514 (17) | 0.43584 (9) | 0.76730 (8) | 0.0228 (3) | |
F30 | 0.28968 (19) | 0.64658 (9) | 0.67800 (9) | 0.0259 (3) | |
F31 | 0.41295 (19) | 0.54429 (9) | 0.56177 (9) | 0.0271 (4) | |
F32 | 0.38986 (17) | 0.38762 (9) | 0.54469 (8) | 0.0234 (3) | |
C29 | 0.2585 (3) | 0.40830 (15) | 0.65651 (14) | 0.0161 (5) | |
C30 | 0.1965 (3) | 0.46280 (16) | 0.71636 (14) | 0.0182 (5) | |
C31 | 0.2045 (3) | 0.54314 (15) | 0.72577 (14) | 0.0166 (5) | |
C32 | 0.2787 (3) | 0.56938 (15) | 0.67263 (14) | 0.0186 (5) | |
C33 | 0.3417 (3) | 0.51713 (16) | 0.61237 (14) | 0.0193 (5) | |
C34 | 0.3307 (3) | 0.43733 (16) | 0.60458 (14) | 0.0183 (5) | |
I3 | 0.39366 (2) | 0.29864 (2) | 0.15711 (2) | 0.02594 (4) | |
I4 | 0.19057 (2) | 0.58106 (2) | 0.39910 (2) | 0.02628 (4) | |
F33 | 0.31982 (19) | 0.47479 (9) | 0.24734 (9) | 0.0278 (4) | |
F34 | 0.11956 (18) | 0.43808 (10) | 0.46524 (9) | 0.0290 (4) | |
F35 | 0.17740 (18) | 0.28360 (10) | 0.41706 (9) | 0.0295 (4) | |
F36 | 0.30202 (17) | 0.22313 (9) | 0.28451 (9) | 0.0256 (3) | |
C35 | 0.2209 (3) | 0.46038 (15) | 0.35750 (15) | 0.0190 (5) | |
C36 | 0.2842 (3) | 0.42746 (16) | 0.28917 (14) | 0.0191 (5) | |
C37 | 0.3114 (3) | 0.34781 (15) | 0.26241 (14) | 0.0178 (5) | |
C38 | 0.2759 (3) | 0.30052 (15) | 0.30711 (15) | 0.0192 (5) | |
C39 | 0.2115 (3) | 0.33102 (16) | 0.37517 (15) | 0.0210 (6) | |
C40 | 0.1836 (3) | 0.40999 (16) | 0.39927 (14) | 0.0200 (5) | |
I5 | 0.82526 (2) | 0.39902 (2) | −0.11345 (2) | 0.02532 (4) | |
I6 | 0.75419 (2) | 0.73973 (2) | 0.07191 (2) | 0.01718 (4) | |
F37 | 0.85766 (18) | 0.58847 (9) | −0.05559 (8) | 0.0244 (3) | |
F38 | 0.59562 (17) | 0.64129 (9) | 0.16783 (8) | 0.0218 (3) | |
F39 | 0.54190 (18) | 0.48581 (9) | 0.14581 (9) | 0.0262 (4) | |
F40 | 0.63996 (18) | 0.38040 (9) | 0.02360 (9) | 0.0255 (3) | |
C41 | 0.7536 (3) | 0.48240 (15) | −0.01841 (14) | 0.0169 (5) | |
C42 | 0.7782 (3) | 0.56261 (15) | −0.00623 (14) | 0.0164 (5) | |
C43 | 0.7249 (3) | 0.61822 (14) | 0.05532 (14) | 0.0149 (5) | |
C44 | 0.6468 (3) | 0.59054 (15) | 0.10618 (14) | 0.0168 (5) | |
C45 | 0.6198 (3) | 0.51085 (15) | 0.09575 (14) | 0.0180 (5) | |
C46 | 0.6721 (3) | 0.45764 (15) | 0.03328 (15) | 0.0182 (5) | |
S1 | 1.26980 (7) | 0.02971 (4) | 0.13364 (4) | 0.01658 (13) | |
N1 | 1.3937 (2) | −0.08314 (13) | 0.19002 (11) | 0.0155 (4) | |
HN1 | 1.487 (2) | −0.0747 (18) | 0.1788 (17) | 0.031 (9)* | |
N2 | 1.1363 (2) | −0.08180 (12) | 0.18912 (11) | 0.0153 (4) | |
HN2 | 1.041 (2) | −0.0708 (15) | 0.1806 (14) | 0.015 (7)* | |
C1 | 1.2668 (3) | −0.04645 (15) | 0.17100 (13) | 0.0158 (5) | |
C2 | 1.3451 (3) | −0.14290 (15) | 0.21949 (13) | 0.0154 (5) | |
C3 | 1.4285 (3) | −0.19430 (15) | 0.24861 (14) | 0.0188 (5) | |
H3 | 1.540814 | −0.194912 | 0.248974 | 0.023* | |
C4 | 1.3406 (3) | −0.24474 (16) | 0.27716 (14) | 0.0208 (6) | |
H4 | 1.393923 | −0.280671 | 0.297743 | 0.025* | |
C5 | 1.1748 (3) | −0.24408 (16) | 0.27645 (14) | 0.0197 (5) | |
H5 | 1.118578 | −0.279849 | 0.296263 | 0.024* | |
C6 | 1.0905 (3) | −0.19247 (15) | 0.24751 (14) | 0.0182 (5) | |
H6 | 0.978144 | −0.191915 | 0.247143 | 0.022* | |
C7 | 1.1792 (3) | −0.14174 (15) | 0.21913 (13) | 0.0159 (5) | |
S2 | 0.76230 (7) | −0.07080 (4) | 0.13517 (3) | 0.01460 (12) | |
N3 | 0.8902 (2) | 0.04164 (12) | 0.07893 (12) | 0.0142 (4) | |
HN3 | 0.985 (2) | 0.0339 (17) | 0.0913 (16) | 0.026 (8)* | |
N4 | 0.6315 (2) | 0.03610 (12) | 0.07390 (11) | 0.0134 (4) | |
HN4 | 0.539 (2) | 0.0257 (15) | 0.0851 (15) | 0.016 (7)* | |
C8 | 0.7619 (3) | 0.00336 (14) | 0.09496 (13) | 0.0135 (5) | |
C9 | 0.8425 (3) | 0.10176 (14) | 0.04983 (13) | 0.0149 (5) | |
C10 | 0.9275 (3) | 0.15703 (15) | 0.02577 (14) | 0.0186 (5) | |
H10 | 1.040174 | 0.160378 | 0.028830 | 0.022* | |
C11 | 0.8386 (3) | 0.20721 (15) | −0.00307 (15) | 0.0199 (5) | |
H11 | 0.892259 | 0.246317 | −0.019649 | 0.024* | |
C12 | 0.6733 (3) | 0.20197 (15) | −0.00842 (14) | 0.0185 (5) | |
H12 | 0.617475 | 0.236637 | −0.029681 | 0.022* | |
C13 | 0.5882 (3) | 0.14726 (15) | 0.01657 (13) | 0.0160 (5) | |
H13 | 0.475508 | 0.143780 | 0.013282 | 0.019* | |
C14 | 0.6767 (3) | 0.09798 (14) | 0.04661 (13) | 0.0137 (5) | |
S3 | 0.21077 (7) | 1.09011 (4) | 0.59658 (4) | 0.01674 (13) | |
N5 | 0.3335 (2) | 0.98621 (12) | 0.66496 (12) | 0.0153 (4) | |
HN5 | 0.427 (2) | 0.9957 (18) | 0.6541 (17) | 0.035 (9)* | |
N6 | 0.0755 (2) | 0.98679 (12) | 0.66091 (12) | 0.0149 (4) | |
HN6 | −0.020 (2) | 0.9958 (16) | 0.6501 (15) | 0.021 (8)* | |
C15 | 0.2063 (3) | 1.02032 (14) | 0.64225 (13) | 0.0147 (5) | |
C16 | 0.2825 (3) | 0.92908 (14) | 0.69697 (13) | 0.0149 (5) | |
C17 | 0.3645 (3) | 0.87884 (15) | 0.72898 (14) | 0.0196 (5) | |
H17 | 0.477019 | 0.878891 | 0.731657 | 0.024* | |
C18 | 0.2730 (3) | 0.82880 (15) | 0.75670 (14) | 0.0211 (6) | |
H18 | 0.324318 | 0.793463 | 0.778775 | 0.025* | |
C19 | 0.1078 (3) | 0.82884 (15) | 0.75312 (14) | 0.0213 (6) | |
H19 | 0.049812 | 0.793080 | 0.772293 | 0.026* | |
C20 | 0.0256 (3) | 0.87954 (15) | 0.72240 (14) | 0.0186 (5) | |
H20 | −0.086842 | 0.880244 | 0.720810 | 0.022* | |
C21 | 0.1171 (3) | 0.92909 (14) | 0.69418 (13) | 0.0141 (5) | |
S4 | −0.29930 (7) | 0.99445 (4) | 0.61172 (3) | 0.01608 (12) | |
N7 | −0.1672 (2) | 1.09905 (13) | 0.54729 (12) | 0.0157 (4) | |
HN7 | −0.073 (2) | 1.0901 (18) | 0.5580 (17) | 0.033 (9)* | |
N8 | −0.4249 (2) | 1.09692 (13) | 0.54319 (12) | 0.0156 (4) | |
HN8 | −0.519 (2) | 1.0848 (17) | 0.5511 (17) | 0.029 (8)* | |
C22 | −0.2972 (3) | 1.06481 (14) | 0.56708 (13) | 0.0146 (5) | |
C23 | −0.2121 (3) | 1.15416 (14) | 0.51139 (13) | 0.0145 (5) | |
C24 | −0.1251 (3) | 1.20294 (15) | 0.48049 (14) | 0.0186 (5) | |
H24 | −0.012656 | 1.203249 | 0.481615 | 0.022* | |
C25 | −0.2099 (3) | 1.25129 (15) | 0.44782 (14) | 0.0189 (5) | |
H25 | −0.154262 | 1.285731 | 0.426292 | 0.023* | |
C26 | −0.3758 (3) | 1.25043 (15) | 0.44591 (14) | 0.0189 (5) | |
H26 | −0.429872 | 1.284470 | 0.423194 | 0.023* | |
C27 | −0.4633 (3) | 1.20121 (15) | 0.47629 (14) | 0.0185 (5) | |
H27 | −0.575825 | 1.200557 | 0.474834 | 0.022* | |
C28 | −0.3778 (3) | 1.15290 (14) | 0.50896 (13) | 0.0147 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
I1 | 0.01909 (8) | 0.01702 (9) | 0.02029 (9) | 0.00047 (6) | −0.00052 (6) | 0.00538 (7) |
I2 | 0.02488 (9) | 0.02320 (9) | 0.01763 (9) | 0.00734 (7) | 0.00435 (7) | 0.00505 (7) |
F29 | 0.0267 (8) | 0.0243 (9) | 0.0207 (8) | 0.0015 (6) | 0.0077 (6) | 0.0105 (7) |
F30 | 0.0389 (9) | 0.0165 (8) | 0.0242 (9) | 0.0008 (7) | 0.0055 (7) | 0.0085 (7) |
F31 | 0.0365 (9) | 0.0267 (9) | 0.0217 (8) | −0.0001 (7) | 0.0121 (7) | 0.0112 (7) |
F32 | 0.0259 (8) | 0.0241 (9) | 0.0192 (8) | 0.0051 (6) | 0.0067 (6) | 0.0034 (7) |
C29 | 0.0157 (12) | 0.0150 (13) | 0.0176 (13) | 0.0003 (9) | −0.0012 (9) | 0.0052 (11) |
C30 | 0.0148 (12) | 0.0233 (14) | 0.0179 (13) | 0.0010 (10) | 0.0011 (10) | 0.0080 (11) |
C31 | 0.0165 (12) | 0.0192 (14) | 0.0134 (12) | 0.0051 (10) | 0.0015 (9) | 0.0035 (10) |
C32 | 0.0210 (13) | 0.0174 (14) | 0.0185 (13) | 0.0012 (10) | −0.0005 (10) | 0.0074 (11) |
C33 | 0.0193 (13) | 0.0244 (15) | 0.0167 (13) | 0.0000 (10) | 0.0034 (10) | 0.0098 (11) |
C34 | 0.0151 (12) | 0.0228 (14) | 0.0154 (13) | 0.0019 (10) | 0.0009 (9) | 0.0030 (11) |
I3 | 0.03176 (10) | 0.02680 (10) | 0.01832 (9) | 0.00506 (7) | 0.00720 (7) | 0.00377 (8) |
I4 | 0.02547 (9) | 0.01905 (9) | 0.02967 (10) | 0.00413 (7) | −0.00068 (7) | 0.00011 (8) |
F33 | 0.0386 (9) | 0.0238 (9) | 0.0252 (9) | 0.0027 (7) | 0.0080 (7) | 0.0127 (7) |
F34 | 0.0306 (9) | 0.0367 (10) | 0.0183 (8) | 0.0053 (7) | 0.0094 (7) | 0.0040 (7) |
F35 | 0.0325 (9) | 0.0313 (10) | 0.0308 (9) | −0.0031 (7) | 0.0084 (7) | 0.0182 (8) |
F36 | 0.0261 (8) | 0.0155 (8) | 0.0351 (10) | 0.0008 (6) | 0.0060 (7) | 0.0067 (7) |
C35 | 0.0159 (12) | 0.0174 (14) | 0.0218 (14) | 0.0018 (10) | −0.0004 (10) | 0.0029 (11) |
C36 | 0.0178 (12) | 0.0221 (14) | 0.0190 (13) | −0.0006 (10) | −0.0005 (10) | 0.0090 (11) |
C37 | 0.0169 (12) | 0.0206 (14) | 0.0149 (13) | 0.0025 (10) | 0.0004 (9) | 0.0035 (11) |
C38 | 0.0142 (12) | 0.0180 (14) | 0.0243 (14) | 0.0006 (10) | −0.0012 (10) | 0.0048 (11) |
C39 | 0.0181 (13) | 0.0272 (15) | 0.0201 (14) | −0.0035 (10) | 0.0008 (10) | 0.0116 (12) |
C40 | 0.0159 (12) | 0.0275 (15) | 0.0151 (13) | 0.0007 (10) | 0.0017 (10) | 0.0039 (11) |
I5 | 0.02794 (9) | 0.02317 (10) | 0.01987 (9) | 0.00810 (7) | 0.00031 (7) | −0.00193 (7) |
I6 | 0.01777 (8) | 0.01347 (8) | 0.02020 (9) | −0.00095 (6) | −0.00012 (6) | 0.00532 (7) |
F37 | 0.0293 (8) | 0.0248 (9) | 0.0215 (8) | 0.0003 (7) | 0.0103 (6) | 0.0092 (7) |
F38 | 0.0267 (8) | 0.0201 (8) | 0.0186 (8) | 0.0047 (6) | 0.0078 (6) | 0.0039 (7) |
F39 | 0.0332 (9) | 0.0240 (9) | 0.0274 (9) | 0.0000 (7) | 0.0085 (7) | 0.0158 (7) |
F40 | 0.0338 (9) | 0.0131 (8) | 0.0291 (9) | −0.0013 (6) | −0.0028 (7) | 0.0066 (7) |
C41 | 0.0172 (12) | 0.0161 (13) | 0.0151 (13) | 0.0049 (10) | −0.0016 (9) | 0.0011 (10) |
C42 | 0.0149 (12) | 0.0198 (14) | 0.0155 (13) | 0.0007 (10) | 0.0013 (9) | 0.0064 (11) |
C43 | 0.0149 (12) | 0.0125 (12) | 0.0174 (13) | 0.0015 (9) | −0.0011 (9) | 0.0049 (10) |
C44 | 0.0162 (12) | 0.0176 (13) | 0.0161 (13) | 0.0027 (10) | 0.0006 (9) | 0.0041 (11) |
C45 | 0.0182 (12) | 0.0182 (14) | 0.0195 (13) | −0.0002 (10) | 0.0004 (10) | 0.0090 (11) |
C46 | 0.0213 (13) | 0.0106 (13) | 0.0217 (14) | −0.0014 (10) | −0.0053 (10) | 0.0050 (11) |
S1 | 0.0117 (3) | 0.0187 (3) | 0.0194 (3) | 0.0011 (2) | 0.0010 (2) | 0.0057 (3) |
N1 | 0.0100 (10) | 0.0206 (12) | 0.0150 (11) | 0.0013 (8) | 0.0013 (8) | 0.0037 (9) |
N2 | 0.0094 (10) | 0.0198 (12) | 0.0169 (11) | 0.0021 (8) | 0.0008 (8) | 0.0057 (9) |
C1 | 0.0141 (12) | 0.0179 (13) | 0.0123 (12) | 0.0001 (9) | 0.0015 (9) | −0.0002 (10) |
C2 | 0.0142 (12) | 0.0165 (13) | 0.0125 (12) | 0.0001 (9) | −0.0003 (9) | 0.0001 (10) |
C3 | 0.0141 (12) | 0.0223 (14) | 0.0182 (13) | 0.0028 (10) | 0.0003 (10) | 0.0029 (11) |
C4 | 0.0229 (13) | 0.0214 (14) | 0.0178 (13) | 0.0037 (11) | −0.0007 (10) | 0.0052 (11) |
C5 | 0.0235 (13) | 0.0191 (14) | 0.0148 (13) | −0.0021 (10) | 0.0026 (10) | 0.0026 (11) |
C6 | 0.0163 (12) | 0.0203 (14) | 0.0157 (13) | −0.0001 (10) | 0.0015 (10) | 0.0019 (11) |
C7 | 0.0165 (12) | 0.0174 (13) | 0.0127 (12) | 0.0013 (10) | −0.0010 (9) | 0.0029 (10) |
S2 | 0.0118 (3) | 0.0130 (3) | 0.0192 (3) | 0.0003 (2) | 0.0004 (2) | 0.0054 (3) |
N3 | 0.0096 (10) | 0.0158 (11) | 0.0180 (11) | 0.0016 (8) | 0.0003 (8) | 0.0061 (9) |
N4 | 0.0112 (10) | 0.0133 (11) | 0.0153 (11) | 0.0011 (8) | 0.0004 (8) | 0.0036 (9) |
C8 | 0.0126 (11) | 0.0128 (12) | 0.0127 (12) | 0.0017 (9) | 0.0000 (9) | 0.0004 (10) |
C9 | 0.0154 (12) | 0.0147 (13) | 0.0138 (12) | 0.0003 (9) | 0.0011 (9) | 0.0030 (10) |
C10 | 0.0148 (12) | 0.0200 (14) | 0.0208 (14) | −0.0018 (10) | 0.0018 (10) | 0.0058 (11) |
C11 | 0.0216 (13) | 0.0173 (14) | 0.0221 (14) | −0.0012 (10) | 0.0041 (10) | 0.0079 (11) |
C12 | 0.0231 (13) | 0.0154 (13) | 0.0167 (13) | 0.0030 (10) | −0.0006 (10) | 0.0045 (11) |
C13 | 0.0146 (12) | 0.0164 (13) | 0.0147 (12) | 0.0044 (9) | 0.0019 (9) | 0.0003 (10) |
C14 | 0.0143 (11) | 0.0126 (12) | 0.0132 (12) | −0.0006 (9) | 0.0027 (9) | 0.0022 (10) |
S3 | 0.0129 (3) | 0.0165 (3) | 0.0224 (3) | 0.0008 (2) | 0.0024 (2) | 0.0079 (3) |
N5 | 0.0123 (10) | 0.0155 (11) | 0.0178 (11) | 0.0017 (8) | 0.0011 (8) | 0.0042 (9) |
N6 | 0.0103 (10) | 0.0145 (11) | 0.0194 (11) | 0.0007 (8) | 0.0007 (8) | 0.0043 (9) |
C15 | 0.0139 (11) | 0.0145 (13) | 0.0142 (12) | 0.0017 (9) | 0.0023 (9) | 0.0015 (10) |
C16 | 0.0165 (12) | 0.0135 (13) | 0.0118 (12) | 0.0002 (9) | −0.0012 (9) | −0.0005 (10) |
C17 | 0.0189 (13) | 0.0204 (14) | 0.0163 (13) | 0.0065 (10) | −0.0022 (10) | 0.0003 (11) |
C18 | 0.0306 (14) | 0.0167 (14) | 0.0141 (13) | 0.0056 (11) | −0.0041 (10) | 0.0022 (11) |
C19 | 0.0300 (14) | 0.0166 (14) | 0.0179 (14) | −0.0005 (11) | 0.0020 (11) | 0.0063 (11) |
C20 | 0.0206 (13) | 0.0167 (13) | 0.0165 (13) | −0.0009 (10) | 0.0015 (10) | 0.0020 (11) |
C21 | 0.0158 (12) | 0.0137 (12) | 0.0108 (12) | 0.0019 (9) | −0.0008 (9) | 0.0007 (10) |
S4 | 0.0130 (3) | 0.0184 (3) | 0.0182 (3) | −0.0002 (2) | 0.0001 (2) | 0.0078 (3) |
N7 | 0.0114 (10) | 0.0195 (12) | 0.0159 (11) | −0.0007 (8) | −0.0008 (8) | 0.0054 (9) |
N8 | 0.0111 (10) | 0.0199 (12) | 0.0168 (11) | −0.0001 (8) | 0.0016 (8) | 0.0070 (9) |
C22 | 0.0146 (12) | 0.0152 (13) | 0.0119 (12) | 0.0007 (9) | −0.0003 (9) | 0.0007 (10) |
C23 | 0.0166 (12) | 0.0127 (12) | 0.0110 (12) | 0.0000 (9) | 0.0001 (9) | −0.0011 (10) |
C24 | 0.0182 (12) | 0.0192 (14) | 0.0164 (13) | −0.0050 (10) | 0.0018 (10) | 0.0028 (11) |
C25 | 0.0254 (13) | 0.0141 (13) | 0.0169 (13) | −0.0022 (10) | 0.0030 (10) | 0.0044 (11) |
C26 | 0.0242 (13) | 0.0166 (13) | 0.0153 (13) | 0.0017 (10) | 0.0009 (10) | 0.0037 (11) |
C27 | 0.0164 (12) | 0.0191 (14) | 0.0187 (13) | 0.0018 (10) | 0.0005 (10) | 0.0035 (11) |
C28 | 0.0162 (12) | 0.0134 (12) | 0.0143 (12) | −0.0012 (9) | 0.0016 (9) | 0.0037 (10) |
I1—C29 | 2.090 (3) | C6—C7 | 1.390 (3) |
I2—C31 | 2.088 (2) | S2—C8 | 1.696 (2) |
F29—C30 | 1.348 (3) | N3—HN3 | 0.846 (17) |
F30—C32 | 1.342 (3) | N3—C8 | 1.354 (3) |
F31—C33 | 1.344 (3) | N3—C9 | 1.394 (3) |
F32—C34 | 1.343 (3) | N4—HN4 | 0.849 (16) |
C29—C30 | 1.392 (3) | N4—C8 | 1.356 (3) |
C29—C34 | 1.387 (3) | N4—C14 | 1.390 (3) |
C30—C31 | 1.382 (4) | C9—C10 | 1.388 (3) |
C31—C32 | 1.387 (3) | C9—C14 | 1.398 (3) |
C32—C33 | 1.382 (4) | C10—H10 | 0.9500 |
C33—C34 | 1.378 (4) | C10—C11 | 1.390 (3) |
I3—C37 | 2.083 (2) | C11—H11 | 0.9500 |
I4—C35 | 2.082 (3) | C11—C12 | 1.394 (3) |
F33—C36 | 1.343 (3) | C12—H12 | 0.9500 |
F34—C40 | 1.344 (3) | C12—C13 | 1.391 (4) |
F35—C39 | 1.342 (3) | C13—H13 | 0.9500 |
F36—C38 | 1.342 (3) | C13—C14 | 1.388 (3) |
C35—C36 | 1.390 (4) | S3—C15 | 1.699 (2) |
C35—C40 | 1.389 (4) | N5—HN5 | 0.850 (17) |
C36—C37 | 1.386 (4) | N5—C15 | 1.360 (3) |
C37—C38 | 1.385 (4) | N5—C16 | 1.388 (3) |
C38—C39 | 1.383 (4) | N6—HN6 | 0.851 (17) |
C39—C40 | 1.373 (4) | N6—C15 | 1.348 (3) |
I5—C41 | 2.092 (2) | N6—C21 | 1.390 (3) |
I6—C43 | 2.088 (2) | C16—C17 | 1.394 (3) |
F37—C42 | 1.347 (3) | C16—C21 | 1.398 (3) |
F38—C44 | 1.345 (3) | C17—H17 | 0.9500 |
F39—C45 | 1.344 (3) | C17—C18 | 1.386 (4) |
F40—C46 | 1.343 (3) | C18—H18 | 0.9500 |
C41—C42 | 1.379 (4) | C18—C19 | 1.396 (4) |
C41—C46 | 1.382 (4) | C19—H19 | 0.9500 |
C42—C43 | 1.390 (3) | C19—C20 | 1.387 (3) |
C43—C44 | 1.382 (3) | C20—H20 | 0.9500 |
C44—C45 | 1.377 (4) | C20—C21 | 1.386 (3) |
C45—C46 | 1.378 (4) | S4—C22 | 1.693 (2) |
S1—C1 | 1.693 (3) | N7—HN7 | 0.844 (17) |
N1—HN1 | 0.847 (17) | N7—C22 | 1.358 (3) |
N1—C1 | 1.358 (3) | N7—C23 | 1.391 (3) |
N1—C2 | 1.390 (3) | N8—HN8 | 0.852 (17) |
N2—HN2 | 0.854 (16) | N8—C22 | 1.353 (3) |
N2—C1 | 1.358 (3) | N8—C28 | 1.389 (3) |
N2—C7 | 1.390 (3) | C23—C24 | 1.386 (3) |
C2—C3 | 1.385 (3) | C23—C28 | 1.398 (3) |
C2—C7 | 1.404 (3) | C24—H24 | 0.9500 |
C3—H3 | 0.9500 | C24—C25 | 1.388 (3) |
C3—C4 | 1.384 (4) | C25—H25 | 0.9500 |
C4—H4 | 0.9500 | C25—C26 | 1.401 (3) |
C4—C5 | 1.402 (3) | C26—H26 | 0.9500 |
C5—H5 | 0.9500 | C26—C27 | 1.388 (4) |
C5—C6 | 1.390 (3) | C27—H27 | 0.9500 |
C6—H6 | 0.9500 | C27—C28 | 1.390 (3) |
C30—C29—I1 | 121.55 (18) | C8—N3—HN3 | 123 (2) |
C34—C29—I1 | 120.98 (19) | C8—N3—C9 | 110.03 (19) |
C34—C29—C30 | 117.4 (2) | C9—N3—HN3 | 126 (2) |
F29—C30—C29 | 118.4 (2) | C8—N4—HN4 | 122.6 (18) |
F29—C30—C31 | 118.6 (2) | C8—N4—C14 | 109.91 (19) |
C31—C30—C29 | 123.0 (2) | C14—N4—HN4 | 126.3 (18) |
C30—C31—I2 | 121.81 (18) | N3—C8—S2 | 126.82 (17) |
C30—C31—C32 | 117.5 (2) | N3—C8—N4 | 107.3 (2) |
C32—C31—I2 | 120.72 (19) | N4—C8—S2 | 125.90 (18) |
F30—C32—C31 | 120.7 (2) | N3—C9—C14 | 106.2 (2) |
F30—C32—C33 | 118.0 (2) | C10—C9—N3 | 132.1 (2) |
C33—C32—C31 | 121.3 (2) | C10—C9—C14 | 121.7 (2) |
F31—C33—C32 | 120.0 (2) | C9—C10—H10 | 121.9 |
F31—C33—C34 | 120.4 (2) | C9—C10—C11 | 116.3 (2) |
C34—C33—C32 | 119.6 (2) | C11—C10—H10 | 121.9 |
F32—C34—C29 | 120.3 (2) | C10—C11—H11 | 119.0 |
F32—C34—C33 | 118.5 (2) | C10—C11—C12 | 122.1 (2) |
C33—C34—C29 | 121.2 (2) | C12—C11—H11 | 119.0 |
C36—C35—I4 | 122.13 (19) | C11—C12—H12 | 119.2 |
C40—C35—I4 | 120.40 (19) | C13—C12—C11 | 121.6 (2) |
C40—C35—C36 | 117.4 (2) | C13—C12—H12 | 119.2 |
F33—C36—C35 | 118.6 (2) | C12—C13—H13 | 121.8 |
F33—C36—C37 | 118.7 (2) | C14—C13—C12 | 116.4 (2) |
C37—C36—C35 | 122.7 (2) | C14—C13—H13 | 121.8 |
C36—C37—I3 | 121.94 (19) | N4—C14—C9 | 106.5 (2) |
C38—C37—I3 | 120.42 (19) | C13—C14—N4 | 131.5 (2) |
C38—C37—C36 | 117.6 (2) | C13—C14—C9 | 121.9 (2) |
F36—C38—C37 | 120.2 (2) | C15—N5—HN5 | 122 (2) |
F36—C38—C39 | 118.4 (2) | C15—N5—C16 | 109.8 (2) |
C39—C38—C37 | 121.4 (2) | C16—N5—HN5 | 128 (2) |
F35—C39—C38 | 120.0 (2) | C15—N6—HN6 | 125.4 (19) |
F35—C39—C40 | 120.6 (2) | C15—N6—C21 | 110.28 (19) |
C40—C39—C38 | 119.4 (2) | C21—N6—HN6 | 124.0 (19) |
F34—C40—C35 | 120.2 (2) | N5—C15—S3 | 126.48 (18) |
F34—C40—C39 | 118.3 (2) | N6—C15—S3 | 126.32 (18) |
C39—C40—C35 | 121.5 (2) | N6—C15—N5 | 107.2 (2) |
C42—C41—I5 | 122.49 (18) | N5—C16—C17 | 132.2 (2) |
C42—C41—C46 | 117.7 (2) | N5—C16—C21 | 106.5 (2) |
C46—C41—I5 | 119.79 (19) | C17—C16—C21 | 121.2 (2) |
F37—C42—C41 | 119.0 (2) | C16—C17—H17 | 121.8 |
F37—C42—C43 | 118.4 (2) | C18—C17—C16 | 116.4 (2) |
C41—C42—C43 | 122.6 (2) | C18—C17—H17 | 121.8 |
C42—C43—I6 | 122.78 (18) | C17—C18—H18 | 119.1 |
C44—C43—I6 | 119.64 (18) | C17—C18—C19 | 121.9 (2) |
C44—C43—C42 | 117.6 (2) | C19—C18—H18 | 119.1 |
F38—C44—C43 | 120.5 (2) | C18—C19—H19 | 119.0 |
F38—C44—C45 | 118.2 (2) | C20—C19—C18 | 122.0 (2) |
C45—C44—C43 | 121.4 (2) | C20—C19—H19 | 119.0 |
F39—C45—C44 | 120.0 (2) | C19—C20—H20 | 122.0 |
F39—C45—C46 | 120.8 (2) | C21—C20—C19 | 116.1 (2) |
C44—C45—C46 | 119.3 (2) | C21—C20—H20 | 122.0 |
F40—C46—C41 | 120.7 (2) | N6—C21—C16 | 106.2 (2) |
F40—C46—C45 | 117.8 (2) | C20—C21—N6 | 131.4 (2) |
C45—C46—C41 | 121.5 (2) | C20—C21—C16 | 122.4 (2) |
C1—N1—HN1 | 123 (2) | C22—N7—HN7 | 124 (2) |
C1—N1—C2 | 110.7 (2) | C22—N7—C23 | 110.29 (19) |
C2—N1—HN1 | 126 (2) | C23—N7—HN7 | 125 (2) |
C1—N2—HN2 | 124.7 (18) | C22—N8—HN8 | 122 (2) |
C1—N2—C7 | 110.48 (19) | C22—N8—C28 | 110.6 (2) |
C7—N2—HN2 | 124.7 (18) | C28—N8—HN8 | 127 (2) |
N1—C1—S1 | 127.03 (19) | N7—C22—S4 | 126.72 (18) |
N1—C1—N2 | 106.5 (2) | N8—C22—S4 | 126.58 (18) |
N2—C1—S1 | 126.41 (18) | N8—C22—N7 | 106.7 (2) |
N1—C2—C7 | 106.0 (2) | N7—C23—C28 | 106.2 (2) |
C3—C2—N1 | 132.4 (2) | C24—C23—N7 | 132.1 (2) |
C3—C2—C7 | 121.6 (2) | C24—C23—C28 | 121.6 (2) |
C2—C3—H3 | 121.5 | C23—C24—H24 | 121.5 |
C4—C3—C2 | 116.9 (2) | C23—C24—C25 | 116.9 (2) |
C4—C3—H3 | 121.5 | C25—C24—H24 | 121.5 |
C3—C4—H4 | 119.2 | C24—C25—H25 | 119.3 |
C3—C4—C5 | 121.6 (2) | C24—C25—C26 | 121.4 (2) |
C5—C4—H4 | 119.2 | C26—C25—H25 | 119.3 |
C4—C5—H5 | 119.1 | C25—C26—H26 | 119.1 |
C6—C5—C4 | 121.8 (2) | C27—C26—C25 | 121.8 (2) |
C6—C5—H5 | 119.1 | C27—C26—H26 | 119.1 |
C5—C6—H6 | 121.8 | C26—C27—H27 | 121.7 |
C7—C6—C5 | 116.5 (2) | C26—C27—C28 | 116.5 (2) |
C7—C6—H6 | 121.8 | C28—C27—H27 | 121.7 |
N2—C7—C2 | 106.3 (2) | N8—C28—C23 | 106.2 (2) |
N2—C7—C6 | 132.0 (2) | N8—C28—C27 | 132.1 (2) |
C6—C7—C2 | 121.6 (2) | C27—C28—C23 | 121.7 (2) |
I1—C29—C30—F29 | 1.8 (3) | N1—C2—C7—C6 | −177.7 (2) |
I1—C29—C30—C31 | −178.02 (18) | C1—N1—C2—C3 | −177.6 (3) |
I1—C29—C34—F32 | −0.7 (3) | C1—N1—C2—C7 | −0.7 (3) |
I1—C29—C34—C33 | 178.45 (19) | C1—N2—C7—C2 | 0.1 (3) |
I2—C31—C32—F30 | −1.4 (3) | C1—N2—C7—C6 | 177.9 (3) |
I2—C31—C32—C33 | 179.38 (19) | C2—N1—C1—S1 | 179.67 (19) |
F29—C30—C31—I2 | 0.8 (3) | C2—N1—C1—N2 | 0.8 (3) |
F29—C30—C31—C32 | 179.9 (2) | C2—C3—C4—C5 | 0.2 (4) |
F30—C32—C33—F31 | 0.7 (4) | C3—C2—C7—N2 | 177.6 (2) |
F30—C32—C33—C34 | −179.2 (2) | C3—C2—C7—C6 | −0.5 (4) |
F31—C33—C34—F32 | −1.3 (4) | C3—C4—C5—C6 | −0.4 (4) |
F31—C33—C34—C29 | 179.6 (2) | C4—C5—C6—C7 | 0.2 (4) |
C29—C30—C31—I2 | −179.37 (18) | C5—C6—C7—N2 | −177.3 (3) |
C29—C30—C31—C32 | −0.3 (4) | C5—C6—C7—C2 | 0.2 (4) |
C30—C29—C34—F32 | −178.6 (2) | C7—N2—C1—S1 | −179.44 (19) |
C30—C29—C34—C33 | 0.5 (4) | C7—N2—C1—N1 | −0.6 (3) |
C30—C31—C32—F30 | 179.5 (2) | C7—C2—C3—C4 | 0.2 (4) |
C30—C31—C32—C33 | 0.3 (4) | N3—C9—C10—C11 | 177.7 (3) |
C31—C32—C33—F31 | 180.0 (2) | N3—C9—C14—N4 | 0.1 (3) |
C31—C32—C33—C34 | 0.1 (4) | N3—C9—C14—C13 | −176.7 (2) |
C32—C33—C34—F32 | 178.6 (2) | C8—N3—C9—C10 | 179.5 (3) |
C32—C33—C34—C29 | −0.5 (4) | C8—N3—C9—C14 | −1.5 (3) |
C34—C29—C30—F29 | 179.7 (2) | C8—N4—C14—C9 | 1.3 (3) |
C34—C29—C30—C31 | −0.1 (4) | C8—N4—C14—C13 | 177.6 (3) |
I3—C37—C38—F36 | 3.5 (3) | C9—N3—C8—S2 | −176.81 (19) |
I3—C37—C38—C39 | −175.80 (19) | C9—N3—C8—N4 | 2.3 (3) |
I4—C35—C36—F33 | −3.1 (3) | C9—C10—C11—C12 | −0.7 (4) |
I4—C35—C36—C37 | 177.10 (19) | C10—C9—C14—N4 | 179.3 (2) |
I4—C35—C40—F34 | 3.5 (3) | C10—C9—C14—C13 | 2.5 (4) |
I4—C35—C40—C39 | −175.96 (19) | C10—C11—C12—C13 | 1.6 (4) |
F33—C36—C37—I3 | −3.5 (3) | C11—C12—C13—C14 | −0.4 (4) |
F33—C36—C37—C38 | 179.1 (2) | C12—C13—C14—N4 | −177.5 (2) |
F35—C39—C40—F34 | −0.8 (4) | C12—C13—C14—C9 | −1.6 (4) |
F35—C39—C40—C35 | 178.7 (2) | C14—N4—C8—S2 | 176.89 (18) |
F36—C38—C39—F35 | 0.3 (4) | C14—N4—C8—N3 | −2.2 (3) |
F36—C38—C39—C40 | −179.9 (2) | C14—C9—C10—C11 | −1.3 (4) |
C35—C36—C37—I3 | 176.28 (19) | N5—C16—C17—C18 | 179.3 (3) |
C35—C36—C37—C38 | −1.2 (4) | N5—C16—C21—N6 | −0.4 (3) |
C36—C35—C40—F34 | −178.9 (2) | N5—C16—C21—C20 | −179.2 (2) |
C36—C35—C40—C39 | 1.6 (4) | C15—N5—C16—C17 | −179.3 (3) |
C36—C37—C38—F36 | −179.0 (2) | C15—N5—C16—C21 | −0.6 (3) |
C36—C37—C38—C39 | 1.7 (4) | C15—N6—C21—C16 | 1.2 (3) |
C37—C38—C39—F35 | 179.6 (2) | C15—N6—C21—C20 | 179.8 (3) |
C37—C38—C39—C40 | −0.6 (4) | C16—N5—C15—S3 | −177.01 (19) |
C38—C39—C40—F34 | 179.4 (2) | C16—N5—C15—N6 | 1.3 (3) |
C38—C39—C40—C35 | −1.1 (4) | C16—C17—C18—C19 | −0.3 (4) |
C40—C35—C36—F33 | 179.3 (2) | C17—C16—C21—N6 | 178.5 (2) |
C40—C35—C36—C37 | −0.4 (4) | C17—C16—C21—C20 | −0.3 (4) |
I5—C41—C42—F37 | −3.0 (3) | C17—C18—C19—C20 | −0.7 (4) |
I5—C41—C42—C43 | 177.25 (18) | C18—C19—C20—C21 | 1.2 (4) |
I5—C41—C46—F40 | 0.8 (3) | C19—C20—C21—N6 | −179.1 (2) |
I5—C41—C46—C45 | −178.55 (18) | C19—C20—C21—C16 | −0.7 (4) |
I6—C43—C44—F38 | −2.9 (3) | C21—N6—C15—S3 | 176.77 (19) |
I6—C43—C44—C45 | 177.54 (18) | C21—N6—C15—N5 | −1.6 (3) |
F37—C42—C43—I6 | 2.7 (3) | C21—C16—C17—C18 | 0.8 (4) |
F37—C42—C43—C44 | −178.6 (2) | N7—C23—C24—C25 | 179.5 (2) |
F38—C44—C45—F39 | 1.2 (3) | N7—C23—C28—N8 | −0.2 (3) |
F38—C44—C45—C46 | −179.6 (2) | N7—C23—C28—C27 | −179.8 (2) |
F39—C45—C46—F40 | 1.2 (3) | C22—N7—C23—C24 | −179.2 (3) |
F39—C45—C46—C41 | −179.4 (2) | C22—N7—C23—C28 | −0.3 (3) |
C41—C42—C43—I6 | −177.57 (18) | C22—N8—C28—C23 | 0.7 (3) |
C41—C42—C43—C44 | 1.1 (4) | C22—N8—C28—C27 | −179.8 (3) |
C42—C41—C46—F40 | 178.0 (2) | C23—N7—C22—S4 | 179.87 (19) |
C42—C41—C46—C45 | −1.3 (4) | C23—N7—C22—N8 | 0.8 (3) |
C42—C43—C44—F38 | 178.4 (2) | C23—C24—C25—C26 | −0.3 (4) |
C42—C43—C44—C45 | −1.2 (4) | C24—C23—C28—N8 | 178.7 (2) |
C43—C44—C45—F39 | −179.2 (2) | C24—C23—C28—C27 | −0.8 (4) |
C43—C44—C45—C46 | 0.0 (4) | C24—C25—C26—C27 | −0.2 (4) |
C44—C45—C46—F40 | −178.1 (2) | C25—C26—C27—C28 | 0.2 (4) |
C44—C45—C46—C41 | 1.3 (4) | C26—C27—C28—N8 | −179.1 (3) |
C46—C41—C42—F37 | 179.8 (2) | C26—C27—C28—C23 | 0.3 (4) |
C46—C41—C42—C43 | 0.1 (4) | C28—N8—C22—S4 | 179.97 (19) |
N1—C2—C3—C4 | 176.7 (3) | C28—N8—C22—N7 | −1.0 (3) |
N1—C2—C7—N2 | 0.4 (3) | C28—C23—C24—C25 | 0.8 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—HN1···S2i | 0.85 (2) | 2.52 (2) | 3.357 (2) | 172 (3) |
N2—HN2···S2 | 0.85 (2) | 2.46 (2) | 3.297 (2) | 166 (2) |
N3—HN3···S1 | 0.85 (2) | 2.51 (2) | 3.348 (2) | 173 (3) |
N4—HN4···S1ii | 0.85 (2) | 2.50 (2) | 3.326 (2) | 166 (2) |
N5—HN5···S4i | 0.85 (2) | 2.49 (2) | 3.326 (2) | 169 (3) |
N6—HN6···S4 | 0.85 (2) | 2.43 (2) | 3.270 (2) | 169 (3) |
C17—H17···F36iii | 0.95 | 2.61 | 3.385 (3) | 139 |
C20—H20···F36iv | 0.95 | 2.51 | 3.235 (3) | 133 |
N7—HN7···S3 | 0.84 (2) | 2.47 (2) | 3.300 (2) | 170 (3) |
N8—HN8···S3ii | 0.85 (2) | 2.48 (2) | 3.302 (2) | 163 (3) |
Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z; (iii) −x+1, −y+1, −z+1; (iv) −x, −y+1, −z+1. |
C6F4I2·C7H6N2S | F(000) = 1024 |
Mr = 552.06 | Dx = 2.351 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 5.5641 (2) Å | Cell parameters from 9812 reflections |
b = 33.1320 (11) Å | θ = 2.5–30.2° |
c = 8.4710 (3) Å | µ = 4.20 mm−1 |
β = 92.754 (1)° | T = 100 K |
V = 1559.82 (9) Å3 | Plate, colourless |
Z = 4 | 0.22 × 0.18 × 0.06 mm |
Bruker D8 Venture Photon 2 diffractometer | 4211 reflections with I > 2σ(I) |
Radiation source: Incoatec IµS | Rint = 0.050 |
φ and ω scans | θmax = 30.2°, θmin = 2.5° |
Absorption correction: multi-scan (SADABS; Bruker, 2017) | h = −7→7 |
Tmin = 0.501, Tmax = 0.746 | k = −46→46 |
45583 measured reflections | l = −11→11 |
4579 independent reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.020 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.044 | w = 1/[σ2(Fo2) + (0.0059P)2 + 1.8833P] where P = (Fo2 + 2Fc2)/3 |
S = 1.12 | (Δ/σ)max = 0.002 |
4579 reflections | Δρmax = 0.49 e Å−3 |
207 parameters | Δρmin = −0.67 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 | 0.61301 (2) | 0.38195 (2) | 0.76376 (2) | 0.01796 (4) | |
I2 | 0.89550 (3) | 0.17772 (2) | 0.69482 (2) | 0.02372 (4) | |
F1 | 1.0451 (2) | 0.33570 (4) | 0.60867 (16) | 0.0251 (3) | |
F2 | 1.1463 (3) | 0.25762 (4) | 0.57675 (17) | 0.0283 (3) | |
F3 | 0.4636 (3) | 0.22323 (4) | 0.85802 (18) | 0.0292 (3) | |
F4 | 0.3576 (2) | 0.30171 (4) | 0.88704 (18) | 0.0285 (3) | |
C8 | 0.6955 (4) | 0.32080 (6) | 0.7457 (2) | 0.0160 (4) | |
C9 | 0.8965 (4) | 0.30829 (6) | 0.6680 (2) | 0.0176 (4) | |
C10 | 0.9499 (4) | 0.26788 (7) | 0.6526 (2) | 0.0182 (4) | |
C11 | 0.8062 (4) | 0.23834 (6) | 0.7151 (2) | 0.0174 (4) | |
C12 | 0.6066 (4) | 0.25062 (7) | 0.7940 (3) | 0.0188 (4) | |
C13 | 0.5531 (4) | 0.29113 (7) | 0.8091 (3) | 0.0193 (4) | |
S1 | 0.58078 (9) | 0.48006 (2) | 0.75000 (6) | 0.01583 (10) | |
N1 | 0.2303 (3) | 0.52614 (5) | 0.8744 (2) | 0.0153 (3) | |
HN1 | 0.276 (5) | 0.5218 (8) | 0.969 (3) | 0.023 (7)* | |
N2 | 0.2252 (3) | 0.52735 (5) | 0.6175 (2) | 0.0149 (3) | |
HN2 | 0.276 (5) | 0.5229 (8) | 0.525 (3) | 0.023 (7)* | |
C1 | 0.3405 (4) | 0.51181 (6) | 0.7471 (2) | 0.0143 (4) | |
C2 | 0.0446 (4) | 0.55224 (6) | 0.8266 (2) | 0.0147 (4) | |
C3 | −0.1194 (4) | 0.57380 (6) | 0.9113 (2) | 0.0180 (4) | |
H00G | −0.116250 | 0.573127 | 1.023460 | 0.022* | |
C4 | −0.2889 (4) | 0.59651 (7) | 0.8238 (3) | 0.0196 (4) | |
H00M | −0.404740 | 0.611727 | 0.877214 | 0.024* | |
C5 | −0.2920 (4) | 0.59733 (7) | 0.6581 (3) | 0.0203 (4) | |
H00J | −0.409996 | 0.613183 | 0.602105 | 0.024* | |
C6 | −0.1275 (4) | 0.57565 (6) | 0.5737 (2) | 0.0186 (4) | |
H00L | −0.130222 | 0.576283 | 0.461502 | 0.022* | |
C7 | 0.0408 (4) | 0.55303 (6) | 0.6613 (2) | 0.0147 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
I1 | 0.02099 (7) | 0.01539 (7) | 0.01731 (7) | 0.00072 (5) | −0.00093 (5) | −0.00014 (5) |
I2 | 0.03021 (8) | 0.01541 (7) | 0.02536 (8) | 0.00224 (6) | −0.00059 (6) | −0.00099 (5) |
F1 | 0.0259 (7) | 0.0215 (6) | 0.0286 (7) | −0.0048 (6) | 0.0099 (6) | 0.0039 (5) |
F2 | 0.0264 (7) | 0.0260 (7) | 0.0339 (8) | 0.0022 (6) | 0.0152 (6) | −0.0012 (6) |
F3 | 0.0255 (7) | 0.0191 (7) | 0.0440 (9) | −0.0047 (6) | 0.0132 (6) | 0.0058 (6) |
F4 | 0.0222 (7) | 0.0248 (7) | 0.0400 (8) | 0.0019 (6) | 0.0160 (6) | 0.0021 (6) |
C8 | 0.0175 (9) | 0.0145 (9) | 0.0159 (9) | 0.0007 (8) | −0.0011 (7) | −0.0006 (7) |
C9 | 0.0195 (10) | 0.0183 (10) | 0.0151 (9) | −0.0039 (8) | 0.0025 (8) | 0.0026 (7) |
C10 | 0.0171 (10) | 0.0210 (10) | 0.0169 (9) | 0.0011 (8) | 0.0036 (8) | −0.0004 (8) |
C11 | 0.0199 (10) | 0.0146 (9) | 0.0174 (10) | −0.0004 (8) | −0.0018 (8) | −0.0009 (7) |
C12 | 0.0187 (10) | 0.0178 (10) | 0.0200 (10) | −0.0040 (8) | 0.0030 (8) | 0.0013 (8) |
C13 | 0.0172 (10) | 0.0202 (10) | 0.0207 (10) | 0.0021 (8) | 0.0041 (8) | −0.0001 (8) |
S1 | 0.0208 (2) | 0.0150 (2) | 0.0116 (2) | 0.00308 (19) | 0.00018 (18) | −0.00025 (16) |
N1 | 0.0177 (8) | 0.0184 (8) | 0.0096 (8) | 0.0020 (7) | −0.0017 (6) | −0.0003 (6) |
N2 | 0.0175 (8) | 0.0172 (8) | 0.0101 (8) | 0.0005 (7) | 0.0010 (6) | −0.0007 (6) |
C1 | 0.0180 (9) | 0.0129 (9) | 0.0119 (8) | −0.0026 (8) | −0.0003 (7) | −0.0004 (7) |
C2 | 0.0150 (9) | 0.0152 (9) | 0.0139 (9) | −0.0016 (8) | −0.0011 (7) | 0.0003 (7) |
C3 | 0.0198 (10) | 0.0191 (10) | 0.0151 (9) | −0.0017 (8) | 0.0010 (8) | −0.0029 (7) |
C4 | 0.0182 (10) | 0.0201 (10) | 0.0206 (10) | 0.0009 (8) | 0.0021 (8) | −0.0022 (8) |
C5 | 0.0191 (10) | 0.0186 (10) | 0.0229 (11) | 0.0009 (8) | −0.0017 (8) | 0.0021 (8) |
C6 | 0.0203 (10) | 0.0212 (10) | 0.0139 (9) | 0.0000 (8) | −0.0021 (8) | 0.0021 (7) |
C7 | 0.0158 (9) | 0.0158 (9) | 0.0125 (9) | −0.0017 (8) | −0.0006 (7) | −0.0007 (7) |
I1—C8 | 2.084 (2) | N1—C2 | 1.393 (3) |
I2—C11 | 2.078 (2) | N2—HN2 | 0.86 (3) |
F1—C9 | 1.342 (2) | N2—C1 | 1.347 (3) |
F2—C10 | 1.338 (2) | N2—C7 | 1.397 (3) |
F3—C12 | 1.338 (2) | C2—C3 | 1.385 (3) |
F4—C13 | 1.346 (2) | C2—C7 | 1.400 (3) |
C8—C9 | 1.388 (3) | C3—H00G | 0.9500 |
C8—C13 | 1.387 (3) | C3—C4 | 1.392 (3) |
C9—C10 | 1.379 (3) | C4—H00M | 0.9500 |
C10—C11 | 1.386 (3) | C4—C5 | 1.402 (3) |
C11—C12 | 1.384 (3) | C5—H00J | 0.9500 |
C12—C13 | 1.382 (3) | C5—C6 | 1.388 (3) |
S1—C1 | 1.700 (2) | C6—H00L | 0.9500 |
N1—HN1 | 0.84 (3) | C6—C7 | 1.387 (3) |
N1—C1 | 1.352 (2) | ||
C9—C8—I1 | 120.68 (15) | C7—N2—HN2 | 128.7 (18) |
C13—C8—I1 | 121.91 (15) | N1—C1—S1 | 126.31 (16) |
C13—C8—C9 | 117.41 (19) | N2—C1—S1 | 126.27 (15) |
F1—C9—C8 | 120.03 (19) | N2—C1—N1 | 107.42 (18) |
F1—C9—C10 | 118.85 (18) | N1—C2—C7 | 106.11 (17) |
C10—C9—C8 | 121.11 (19) | C3—C2—N1 | 131.90 (19) |
F2—C10—C9 | 118.48 (19) | C3—C2—C7 | 121.97 (19) |
F2—C10—C11 | 120.25 (19) | C2—C3—H00G | 121.6 |
C9—C10—C11 | 121.27 (19) | C2—C3—C4 | 116.70 (19) |
C10—C11—I2 | 120.42 (15) | C4—C3—H00G | 121.6 |
C12—C11—I2 | 121.65 (16) | C3—C4—H00M | 119.4 |
C12—C11—C10 | 117.92 (19) | C3—C4—C5 | 121.2 (2) |
F3—C12—C11 | 120.16 (19) | C5—C4—H00M | 119.4 |
F3—C12—C13 | 119.09 (19) | C4—C5—H00J | 119.0 |
C13—C12—C11 | 120.75 (19) | C6—C5—C4 | 121.9 (2) |
F4—C13—C8 | 119.71 (19) | C6—C5—H00J | 119.0 |
F4—C13—C12 | 118.75 (19) | C5—C6—H00L | 121.7 |
C12—C13—C8 | 121.54 (19) | C7—C6—C5 | 116.65 (19) |
C1—N1—HN1 | 125.0 (18) | C7—C6—H00L | 121.7 |
C1—N1—C2 | 110.19 (17) | N2—C7—C2 | 106.19 (17) |
C2—N1—HN1 | 124.6 (18) | C6—C7—N2 | 132.27 (18) |
C1—N2—HN2 | 121.0 (19) | C6—C7—C2 | 121.53 (19) |
C1—N2—C7 | 110.07 (17) | ||
I1—C8—C9—F1 | 2.5 (3) | C13—C8—C9—F1 | −177.88 (19) |
I1—C8—C9—C10 | −178.66 (16) | C13—C8—C9—C10 | 1.0 (3) |
I1—C8—C13—F4 | −1.1 (3) | N1—C2—C3—C4 | −178.1 (2) |
I1—C8—C13—C12 | 178.80 (17) | N1—C2—C7—N2 | −0.1 (2) |
I2—C11—C12—F3 | −0.8 (3) | N1—C2—C7—C6 | 178.62 (19) |
I2—C11—C12—C13 | 178.65 (17) | C1—N1—C2—C3 | 179.2 (2) |
F1—C9—C10—F2 | −1.0 (3) | C1—N1—C2—C7 | 1.0 (2) |
F1—C9—C10—C11 | 178.30 (19) | C1—N2—C7—C2 | −0.9 (2) |
F2—C10—C11—I2 | 0.8 (3) | C1—N2—C7—C6 | −179.4 (2) |
F2—C10—C11—C12 | 179.3 (2) | C2—N1—C1—S1 | 178.30 (15) |
F3—C12—C13—F4 | −0.4 (3) | C2—N1—C1—N2 | −1.6 (2) |
F3—C12—C13—C8 | 179.7 (2) | C2—C3—C4—C5 | 0.0 (3) |
C8—C9—C10—F2 | −179.86 (19) | C3—C2—C7—N2 | −178.50 (19) |
C8—C9—C10—C11 | −0.6 (3) | C3—C2—C7—C6 | 0.2 (3) |
C9—C8—C13—F4 | 179.28 (19) | C3—C4—C5—C6 | 0.1 (3) |
C9—C8—C13—C12 | −0.8 (3) | C4—C5—C6—C7 | 0.0 (3) |
C9—C10—C11—I2 | −178.52 (17) | C5—C6—C7—N2 | 178.2 (2) |
C9—C10—C11—C12 | 0.0 (3) | C5—C6—C7—C2 | −0.1 (3) |
C10—C11—C12—F3 | −179.3 (2) | C7—N2—C1—S1 | −178.36 (15) |
C10—C11—C12—C13 | 0.2 (3) | C7—N2—C1—N1 | 1.5 (2) |
C11—C12—C13—F4 | −179.8 (2) | C7—C2—C3—C4 | −0.1 (3) |
C11—C12—C13—C8 | 0.3 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—HN1···S1i | 0.84 (3) | 2.47 (3) | 3.3089 (18) | 172 (2) |
N2—HN2···S1ii | 0.86 (3) | 2.50 (3) | 3.3527 (17) | 172 (2) |
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x+1, −y+1, −z+1. |
C2I4·C7H6N2S | Dx = 3.053 Mg m−3 |
Mr = 681.82 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pnma | Cell parameters from 32859 reflections |
a = 11.7547 (10) Å | θ = 2.2–28.5° |
b = 8.3525 (7) Å | µ = 8.52 mm−1 |
c = 15.1077 (13) Å | T = 100 K |
V = 1483.3 (2) Å3 | Plank, colourless |
Z = 4 | 0.30 × 0.14 × 0.11 mm |
F(000) = 1208 |
Bruker D8 Venture Photon 2 diffractometer | 1885 reflections with I > 2σ(I) |
Radiation source: Incoatec IµS | Rint = 0.055 |
φ and ω scans | θmax = 28.5°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2017) | h = −15→15 |
Tmin = 0.256, Tmax = 0.746 | k = −11→11 |
32859 measured reflections | l = −20→20 |
1993 independent reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.026 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.062 | w = 1/[σ2(Fo2) + (0.0213P)2 + 6.7951P] where P = (Fo2 + 2Fc2)/3 |
S = 1.25 | (Δ/σ)max = 0.001 |
1993 reflections | Δρmax = 1.25 e Å−3 |
89 parameters | Δρmin = −1.48 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 | 0.71885 (3) | 0.250000 | 0.41396 (2) | 0.01158 (9) | |
I2 | 0.48169 (3) | 0.250000 | 0.27066 (2) | 0.01399 (9) | |
I3 | 0.29263 (3) | 0.250000 | 0.46197 (2) | 0.01401 (9) | |
I4 | 0.52953 (3) | 0.250000 | 0.60280 (2) | 0.02001 (10) | |
C5 | 0.5414 (5) | 0.250000 | 0.4030 (4) | 0.0165 (11) | |
C6 | 0.4724 (5) | 0.250000 | 0.4721 (4) | 0.0174 (11) | |
S1 | 1.01449 (11) | 0.250000 | 0.45747 (8) | 0.0100 (2) | |
N1 | 0.9064 (3) | 0.3808 (4) | 0.5997 (2) | 0.0103 (6) | |
HN1 | 0.925 (4) | 0.478 (6) | 0.586 (3) | 0.016 (12)* | |
C1 | 0.9436 (4) | 0.250000 | 0.5556 (3) | 0.0113 (10) | |
C2 | 0.8394 (3) | 0.3332 (4) | 0.6716 (2) | 0.0101 (7) | |
C3 | 0.7765 (3) | 0.4217 (5) | 0.7322 (2) | 0.0124 (7) | |
H3 | 0.776830 | 0.535466 | 0.732234 | 0.015* | |
C4 | 0.7128 (3) | 0.3335 (5) | 0.7928 (2) | 0.0134 (7) | |
H4 | 0.668132 | 0.388696 | 0.835332 | 0.016* |
U11 | U22 | U33 | U12 | U13 | U23 | |
I1 | 0.00779 (16) | 0.01634 (17) | 0.01059 (16) | 0.000 | −0.00164 (11) | 0.000 |
I2 | 0.01027 (17) | 0.02331 (19) | 0.00839 (16) | 0.000 | −0.00137 (11) | 0.000 |
I3 | 0.00843 (16) | 0.01822 (18) | 0.01538 (17) | 0.000 | 0.00119 (12) | 0.000 |
I4 | 0.01263 (18) | 0.0392 (2) | 0.00821 (17) | 0.000 | −0.00150 (12) | 0.000 |
C5 | 0.012 (3) | 0.023 (3) | 0.014 (3) | 0.000 | −0.002 (2) | 0.000 |
C6 | 0.019 (3) | 0.025 (3) | 0.008 (2) | 0.000 | −0.004 (2) | 0.000 |
S1 | 0.0102 (5) | 0.0095 (5) | 0.0102 (5) | 0.000 | 0.0029 (4) | 0.000 |
N1 | 0.0103 (14) | 0.0088 (14) | 0.0117 (14) | −0.0008 (11) | 0.0015 (11) | −0.0004 (11) |
C1 | 0.008 (2) | 0.014 (2) | 0.012 (2) | 0.000 | −0.0048 (18) | 0.000 |
C2 | 0.0090 (15) | 0.0123 (18) | 0.0090 (15) | 0.0000 (13) | −0.0024 (12) | −0.0001 (13) |
C3 | 0.0132 (17) | 0.0116 (16) | 0.0125 (16) | 0.0013 (13) | 0.0002 (13) | −0.0011 (13) |
C4 | 0.0109 (16) | 0.0172 (19) | 0.0119 (16) | 0.0023 (14) | 0.0030 (13) | −0.0017 (14) |
I1—C5 | 2.093 (6) | N1—C2 | 1.400 (4) |
I2—C5 | 2.119 (6) | C2—C2i | 1.390 (7) |
I3—C6 | 2.118 (6) | C2—C3 | 1.389 (5) |
I4—C6 | 2.086 (5) | C3—H3 | 0.9500 |
C5—C6 | 1.321 (8) | C3—C4 | 1.393 (5) |
S1—C1 | 1.701 (6) | C4—C4i | 1.395 (8) |
N1—HN1 | 0.87 (5) | C4—H4 | 0.9500 |
N1—C1 | 1.352 (4) | ||
I1—C5—I2 | 113.9 (3) | N1i—C1—N1 | 107.8 (5) |
C6—C5—I1 | 123.3 (4) | C2i—C2—N1 | 106.5 (2) |
C6—C5—I2 | 122.8 (4) | C3—C2—N1 | 131.3 (3) |
I4—C6—I3 | 112.9 (3) | C3—C2—C2i | 122.2 (2) |
C5—C6—I3 | 123.7 (4) | C2—C3—H3 | 122.1 |
C5—C6—I4 | 123.3 (5) | C2—C3—C4 | 115.9 (3) |
C1—N1—HN1 | 124 (3) | C4—C3—H3 | 122.1 |
C1—N1—C2 | 109.6 (3) | C3—C4—C4i | 121.9 (2) |
C2—N1—HN1 | 127 (3) | C3—C4—H4 | 119.0 |
N1—C1—S1 | 126.0 (2) | C4i—C4—H4 | 119.0 |
N1i—C1—S1 | 126.0 (2) | ||
I1—C5—C6—I3 | 180.000 (1) | C1—N1—C2—C3 | −174.9 (4) |
I1—C5—C6—I4 | 0.000 (1) | C2—N1—C1—S1 | 172.5 (3) |
I2—C5—C6—I3 | 0.000 (1) | C2—N1—C1—N1i | −2.6 (5) |
I2—C5—C6—I4 | 180.000 (1) | C2i—C2—C3—C4 | −0.3 (4) |
N1—C2—C3—C4 | 175.8 (4) | C2—C3—C4—C4i | 0.3 (4) |
C1—N1—C2—C2i | 1.6 (3) |
Symmetry code: (i) x, −y+1/2, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—HN1···S1ii | 0.87 (5) | 2.47 (5) | 3.335 (3) | 178 (5) |
C3—H3···I1iii | 0.95 | 3.28 | 3.881 (4) | 123 |
Symmetry codes: (ii) −x+2, −y+1, −z+1; (iii) −x+3/2, −y+1, z+1/2. |
C6F4I2·C8H8N2S | Z = 2 |
Mr = 566.08 | F(000) = 528 |
Triclinic, P1 | Dx = 2.321 Mg m−3 |
a = 4.5504 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 13.2872 (14) Å | Cell parameters from 9940 reflections |
c = 13.8064 (14) Å | θ = 2.3–27.5° |
α = 94.766 (4)° | µ = 4.05 mm−1 |
β = 98.124 (4)° | T = 100 K |
γ = 99.588 (4)° | Needle, colourless |
V = 809.97 (15) Å3 | 0.19 × 0.07 × 0.04 mm |
Bruker D8 Venture Photon 2 diffractometer | 3174 reflections with I > 2σ(I) |
Radiation source: Incoatec IµS | Rint = 0.042 |
φ and ω scans | θmax = 27.5°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2017) | h = −5→5 |
Tmin = 0.636, Tmax = 0.746 | k = −17→17 |
21426 measured reflections | l = −17→17 |
3704 independent reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.026 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.055 | w = 1/[σ2(Fo2) + 2.2494P] where P = (Fo2 + 2Fc2)/3 |
S = 1.24 | (Δ/σ)max < 0.001 |
3704 reflections | Δρmax = 1.33 e Å−3 |
217 parameters | Δρmin = −1.06 e Å−3 |
1 restraint |
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 | 0.65636 (6) | 0.37716 (2) | 0.58352 (2) | 0.02050 (7) | |
I2 | 0.65659 (5) | 0.36653 (2) | 0.30961 (2) | 0.01661 (7) | |
F1 | 0.1607 (5) | 0.17992 (18) | 0.21872 (16) | 0.0254 (5) | |
F2 | −0.2407 (6) | 0.04739 (19) | 0.29154 (19) | 0.0334 (6) | |
F3 | −0.2418 (6) | 0.05622 (19) | 0.4886 (2) | 0.0326 (6) | |
F4 | 0.1622 (6) | 0.1944 (2) | 0.61205 (17) | 0.0280 (6) | |
C9 | 0.3758 (8) | 0.2652 (3) | 0.4798 (3) | 0.0154 (7) | |
C10 | 0.3778 (8) | 0.2613 (3) | 0.3784 (3) | 0.0151 (7) | |
C11 | 0.1718 (9) | 0.1857 (3) | 0.3168 (3) | 0.0174 (8) | |
C12 | −0.0361 (9) | 0.1169 (3) | 0.3527 (3) | 0.0206 (8) | |
C13 | −0.0373 (9) | 0.1222 (3) | 0.4535 (3) | 0.0206 (8) | |
C14 | 0.1684 (9) | 0.1943 (3) | 0.5145 (3) | 0.0182 (8) | |
S1 | −0.0441 (2) | 0.50172 (8) | 0.83086 (7) | 0.0204 (2) | |
N1 | 0.2256 (7) | 0.3842 (3) | 0.9578 (2) | 0.0184 (7) | |
HN1 | 0.165 (10) | 0.414 (4) | 1.008 (4) | 0.029 (13)* | |
N2 | 0.2606 (7) | 0.3443 (2) | 0.8049 (2) | 0.0165 (7) | |
HN2 | 0.254 (9) | 0.349 (3) | 0.7436 (15) | 0.009 (10)* | |
C1 | 0.1504 (9) | 0.4093 (3) | 0.8658 (3) | 0.0186 (8) | |
C2 | 0.3863 (8) | 0.3038 (3) | 0.9558 (3) | 0.0172 (8) | |
C3 | 0.5098 (9) | 0.2511 (3) | 1.0292 (3) | 0.0215 (8) | |
H3 | 0.493986 | 0.267954 | 1.096235 | 0.026* | |
C4 | 0.6580 (9) | 0.1726 (3) | 1.0008 (3) | 0.0222 (8) | |
H4 | 0.745045 | 0.135500 | 1.049815 | 0.027* | |
C5 | 0.6828 (9) | 0.1464 (3) | 0.9019 (3) | 0.0227 (9) | |
C6 | 0.5606 (9) | 0.2004 (3) | 0.8290 (3) | 0.0180 (8) | |
H6 | 0.578792 | 0.184847 | 0.761942 | 0.022* | |
C7 | 0.4108 (9) | 0.2782 (3) | 0.8579 (3) | 0.0176 (8) | |
C8 | 0.8415 (9) | 0.0590 (3) | 0.8758 (3) | 0.0245 (9) | |
H8A | 0.727133 | −0.005523 | 0.890936 | 0.037* | |
H8B | 1.044903 | 0.071430 | 0.914124 | 0.037* | |
H8C | 0.855211 | 0.054270 | 0.805416 | 0.037* |
U11 | U22 | U33 | U12 | U13 | U23 | |
I1 | 0.02224 (14) | 0.02260 (14) | 0.01557 (12) | 0.00692 (10) | −0.00119 (9) | −0.00285 (10) |
I2 | 0.01925 (13) | 0.01578 (12) | 0.01588 (12) | 0.00435 (9) | 0.00466 (9) | 0.00245 (9) |
F1 | 0.0295 (13) | 0.0253 (13) | 0.0173 (11) | −0.0002 (10) | −0.0002 (10) | −0.0036 (10) |
F2 | 0.0269 (14) | 0.0274 (14) | 0.0386 (15) | −0.0070 (11) | −0.0003 (11) | −0.0060 (11) |
F3 | 0.0246 (13) | 0.0283 (14) | 0.0489 (17) | 0.0016 (11) | 0.0171 (12) | 0.0143 (12) |
F4 | 0.0320 (14) | 0.0389 (15) | 0.0181 (12) | 0.0110 (11) | 0.0106 (10) | 0.0116 (11) |
C9 | 0.0157 (18) | 0.0167 (18) | 0.0136 (17) | 0.0051 (15) | 0.0014 (14) | −0.0022 (14) |
C10 | 0.0173 (18) | 0.0148 (18) | 0.0135 (17) | 0.0033 (14) | 0.0024 (14) | 0.0016 (14) |
C11 | 0.0205 (19) | 0.0172 (19) | 0.0151 (18) | 0.0071 (15) | 0.0012 (14) | 0.0000 (15) |
C12 | 0.0161 (19) | 0.0167 (19) | 0.027 (2) | 0.0010 (15) | 0.0000 (15) | −0.0015 (16) |
C13 | 0.0132 (18) | 0.0170 (19) | 0.035 (2) | 0.0052 (15) | 0.0101 (16) | 0.0061 (17) |
C14 | 0.021 (2) | 0.021 (2) | 0.0155 (18) | 0.0099 (16) | 0.0041 (15) | 0.0056 (15) |
S1 | 0.0227 (5) | 0.0197 (5) | 0.0214 (5) | 0.0062 (4) | 0.0081 (4) | 0.0052 (4) |
N1 | 0.0228 (18) | 0.0185 (17) | 0.0150 (16) | 0.0047 (14) | 0.0065 (13) | 0.0005 (13) |
N2 | 0.0214 (17) | 0.0202 (17) | 0.0102 (15) | 0.0073 (13) | 0.0045 (12) | 0.0037 (13) |
C1 | 0.021 (2) | 0.0172 (19) | 0.0179 (19) | −0.0010 (15) | 0.0066 (15) | 0.0044 (15) |
C2 | 0.0175 (19) | 0.0193 (19) | 0.0152 (18) | 0.0014 (15) | 0.0063 (14) | 0.0018 (15) |
C3 | 0.024 (2) | 0.029 (2) | 0.0122 (18) | 0.0037 (17) | 0.0042 (15) | 0.0039 (16) |
C4 | 0.020 (2) | 0.026 (2) | 0.019 (2) | 0.0011 (17) | −0.0010 (15) | 0.0054 (16) |
C5 | 0.0158 (19) | 0.025 (2) | 0.026 (2) | 0.0015 (16) | 0.0018 (16) | 0.0020 (17) |
C6 | 0.0193 (19) | 0.0207 (19) | 0.0145 (18) | 0.0041 (16) | 0.0039 (15) | 0.0014 (15) |
C7 | 0.0192 (19) | 0.0186 (19) | 0.0146 (18) | 0.0027 (15) | 0.0023 (14) | 0.0018 (15) |
C8 | 0.020 (2) | 0.026 (2) | 0.029 (2) | 0.0066 (17) | 0.0019 (17) | 0.0049 (18) |
I1—C9 | 2.095 (4) | N2—HN2 | 0.850 (18) |
I2—C10 | 2.106 (4) | N2—C1 | 1.358 (5) |
F1—C11 | 1.344 (4) | N2—C7 | 1.393 (5) |
F2—C12 | 1.340 (4) | C2—C3 | 1.385 (5) |
F3—C13 | 1.340 (4) | C2—C7 | 1.391 (5) |
F4—C14 | 1.352 (4) | C3—H3 | 0.9500 |
C9—C10 | 1.399 (5) | C3—C4 | 1.392 (6) |
C9—C14 | 1.383 (5) | C4—H4 | 0.9500 |
C10—C11 | 1.389 (5) | C4—C5 | 1.406 (6) |
C11—C12 | 1.377 (6) | C5—C6 | 1.390 (5) |
C12—C13 | 1.389 (6) | C5—C8 | 1.511 (6) |
C13—C14 | 1.358 (6) | C6—H6 | 0.9500 |
S1—C1 | 1.693 (4) | C6—C7 | 1.391 (5) |
N1—HN1 | 0.88 (5) | C8—H8A | 0.9800 |
N1—C1 | 1.351 (5) | C8—H8B | 0.9800 |
N1—C2 | 1.392 (5) | C8—H8C | 0.9800 |
C10—C9—I1 | 123.8 (3) | N2—C1—S1 | 125.9 (3) |
C14—C9—I1 | 117.3 (3) | C3—C2—N1 | 132.5 (4) |
C14—C9—C10 | 118.8 (3) | C3—C2—C7 | 120.7 (4) |
C9—C10—I2 | 125.0 (3) | C7—C2—N1 | 106.9 (3) |
C11—C10—I2 | 116.6 (3) | C2—C3—H3 | 121.3 |
C11—C10—C9 | 118.3 (4) | C2—C3—C4 | 117.4 (4) |
F1—C11—C10 | 120.6 (3) | C4—C3—H3 | 121.3 |
F1—C11—C12 | 117.3 (3) | C3—C4—H4 | 119.0 |
C12—C11—C10 | 122.0 (4) | C3—C4—C5 | 122.1 (4) |
F2—C12—C11 | 120.9 (4) | C5—C4—H4 | 119.0 |
F2—C12—C13 | 120.0 (4) | C4—C5—C8 | 119.4 (4) |
C11—C12—C13 | 119.1 (4) | C6—C5—C4 | 120.0 (4) |
F3—C13—C12 | 119.2 (4) | C6—C5—C8 | 120.6 (4) |
F3—C13—C14 | 121.4 (4) | C5—C6—H6 | 121.2 |
C14—C13—C12 | 119.3 (4) | C5—C6—C7 | 117.5 (4) |
F4—C14—C9 | 120.6 (3) | C7—C6—H6 | 121.2 |
F4—C14—C13 | 116.9 (4) | C2—C7—N2 | 105.5 (3) |
C13—C14—C9 | 122.5 (4) | C6—C7—N2 | 132.2 (3) |
C1—N1—HN1 | 121 (3) | C6—C7—C2 | 122.3 (3) |
C1—N1—C2 | 110.4 (3) | C5—C8—H8A | 109.5 |
C2—N1—HN1 | 128 (3) | C5—C8—H8B | 109.5 |
C1—N2—HN2 | 124 (3) | C5—C8—H8C | 109.5 |
C1—N2—C7 | 111.0 (3) | H8A—C8—H8B | 109.5 |
C7—N2—HN2 | 125 (3) | H8A—C8—H8C | 109.5 |
N1—C1—S1 | 127.9 (3) | H8B—C8—H8C | 109.5 |
N1—C1—N2 | 106.2 (3) | ||
I1—C9—C10—I2 | −0.5 (5) | C14—C9—C10—C11 | −0.4 (5) |
I1—C9—C10—C11 | −177.4 (3) | N1—C2—C3—C4 | 179.6 (4) |
I1—C9—C14—F4 | −3.9 (5) | N1—C2—C7—N2 | −0.5 (4) |
I1—C9—C14—C13 | 175.8 (3) | N1—C2—C7—C6 | 179.7 (4) |
I2—C10—C11—F1 | 1.7 (5) | C1—N1—C2—C3 | −179.6 (4) |
I2—C10—C11—C12 | −175.5 (3) | C1—N1—C2—C7 | 0.0 (4) |
F1—C11—C12—F2 | −0.1 (5) | C1—N2—C7—C2 | 0.8 (4) |
F1—C11—C12—C13 | −178.3 (3) | C1—N2—C7—C6 | −179.4 (4) |
F2—C12—C13—F3 | 1.0 (5) | C2—N1—C1—S1 | −180.0 (3) |
F2—C12—C13—C14 | −178.9 (3) | C2—N1—C1—N2 | 0.5 (4) |
F3—C13—C14—F4 | 1.7 (5) | C2—C3—C4—C5 | −0.2 (6) |
F3—C13—C14—C9 | −178.0 (3) | C3—C2—C7—N2 | 179.2 (4) |
C9—C10—C11—F1 | 178.8 (3) | C3—C2—C7—C6 | −0.7 (6) |
C9—C10—C11—C12 | 1.5 (6) | C3—C4—C5—C6 | 0.8 (6) |
C10—C9—C14—F4 | 179.0 (3) | C3—C4—C5—C8 | −178.8 (4) |
C10—C9—C14—C13 | −1.3 (6) | C4—C5—C6—C7 | −1.3 (6) |
C10—C11—C12—F2 | 177.2 (3) | C5—C6—C7—N2 | −178.5 (4) |
C10—C11—C12—C13 | −1.0 (6) | C5—C6—C7—C2 | 1.3 (6) |
C11—C12—C13—F3 | 179.2 (3) | C7—N2—C1—S1 | 179.6 (3) |
C11—C12—C13—C14 | −0.7 (6) | C7—N2—C1—N1 | −0.8 (4) |
C12—C13—C14—F4 | −178.4 (3) | C7—C2—C3—C4 | 0.1 (6) |
C12—C13—C14—C9 | 1.9 (6) | C8—C5—C6—C7 | 178.3 (4) |
C14—C9—C10—I2 | 176.4 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—HN1···S1i | 0.88 (5) | 2.57 (5) | 3.444 (3) | 173 (4) |
N2—HN2···I1 | 0.85 (2) | 3.07 (3) | 3.780 (3) | 142 (3) |
N2—HN2···F4 | 0.85 (2) | 2.56 (3) | 3.122 (4) | 124 (3) |
C3—H3···I2ii | 0.95 | 3.06 | 3.966 (4) | 160 |
C6—H6···F4 | 0.95 | 2.63 | 3.262 (4) | 125 |
Symmetry codes: (i) −x, −y+1, −z+2; (ii) x, y, z+1. |
C6F4I2·2C8H8N2S·2(H2O) | Z = 1 |
Mr = 766.34 | F(000) = 370 |
Triclinic, P1 | Dx = 2.000 Mg m−3 |
a = 4.9088 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.4670 (8) Å | Cell parameters from 9704 reflections |
c = 11.9686 (8) Å | θ = 3.0–29.6° |
α = 106.644 (2)° | µ = 2.69 mm−1 |
β = 98.058 (2)° | T = 100 K |
γ = 92.811 (2)° | Plate, colourless |
V = 636.27 (7) Å3 | 0.31 × 0.11 × 0.08 mm |
Bruker D8 Venture Photon 2 diffractometer | 3500 reflections with I > 2σ(I) |
Radiation source: Incoatec IµS | Rint = 0.036 |
φ and ω scans | θmax = 29.7°, θmin = 3.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2017) | h = −6→6 |
Tmin = 0.536, Tmax = 0.746 | k = −15→15 |
31584 measured reflections | l = −16→16 |
3558 independent reflections |
Refinement on F2 | 7 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.014 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.034 | w = 1/[σ2(Fo2) + 0.4884P] where P = (Fo2 + 2Fc2)/3 |
S = 1.18 | (Δ/σ)max = 0.002 |
3558 reflections | Δρmax = 0.44 e Å−3 |
184 parameters | Δρmin = −0.42 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) | |
I1 | 0.44701 (2) | 0.37987 (2) | 0.76749 (2) | 0.01303 (3) | |
F1 | 0.8875 (2) | 0.62085 (8) | 0.83664 (8) | 0.02138 (19) | |
F2 | 1.31349 (19) | 0.70566 (8) | 1.01073 (9) | 0.02069 (19) | |
C9 | 0.7732 (3) | 0.45489 (12) | 0.90761 (12) | 0.0132 (2) | |
C10 | 0.9374 (3) | 0.56045 (13) | 0.91719 (13) | 0.0143 (3) | |
C11 | 1.1591 (3) | 0.60420 (12) | 1.00759 (13) | 0.0145 (3) | |
S1 | 1.03801 (7) | 0.78475 (3) | 0.43889 (3) | 0.01464 (7) | |
N1 | 0.7347 (3) | 0.75457 (11) | 0.60568 (11) | 0.0147 (2) | |
HN1 | 0.770 (4) | 0.6828 (15) | 0.5977 (19) | 0.023 (5)* | |
N2 | 0.7391 (3) | 0.93710 (11) | 0.58449 (11) | 0.0138 (2) | |
HN2 | 0.788 (4) | 1.0008 (16) | 0.5627 (18) | 0.025 (5)* | |
C1 | 0.8342 (3) | 0.82603 (13) | 0.54519 (12) | 0.0136 (2) | |
C2 | 0.5751 (3) | 0.82008 (13) | 0.68510 (13) | 0.0136 (2) | |
C3 | 0.5789 (3) | 0.93718 (12) | 0.67155 (12) | 0.0129 (2) | |
C4 | 0.4354 (3) | 1.02719 (13) | 0.73639 (13) | 0.0154 (3) | |
H4 | 0.437594 | 1.106246 | 0.725878 | 0.018* | |
C5 | 0.2880 (3) | 0.99734 (13) | 0.81756 (13) | 0.0157 (3) | |
C6 | 0.2857 (3) | 0.87925 (14) | 0.83004 (13) | 0.0173 (3) | |
H6 | 0.183714 | 0.860585 | 0.885580 | 0.021* | |
C7 | 0.4267 (3) | 0.78842 (14) | 0.76427 (14) | 0.0176 (3) | |
H7 | 0.421629 | 0.708673 | 0.773170 | 0.021* | |
C8 | 0.1331 (3) | 1.09189 (15) | 0.89265 (14) | 0.0207 (3) | |
H8A | −0.041876 | 1.052972 | 0.901230 | 0.031* | |
H8B | 0.095344 | 1.155912 | 0.854696 | 0.031* | |
H8C | 0.245015 | 1.128188 | 0.970784 | 0.031* | |
O1 | 0.7691 (3) | 0.49501 (11) | 0.54916 (12) | 0.0247 (2) | |
H1AO | 0.936 (5) | 0.503 (4) | 0.532 (4) | 0.023 (10)* | 0.5 |
H1BO | 0.594 (5) | 0.486 (4) | 0.516 (4) | 0.034 (13)* | 0.5 |
H2O1 | 0.778 (6) | 0.432 (2) | 0.575 (3) | 0.063 (9)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
I1 | 0.01281 (5) | 0.01303 (5) | 0.01267 (5) | 0.00156 (3) | 0.00261 (3) | 0.00256 (3) |
F1 | 0.0247 (5) | 0.0200 (4) | 0.0214 (4) | −0.0027 (4) | −0.0034 (4) | 0.0133 (4) |
F2 | 0.0216 (4) | 0.0163 (4) | 0.0242 (5) | −0.0061 (3) | −0.0011 (4) | 0.0096 (4) |
C9 | 0.0124 (6) | 0.0130 (6) | 0.0129 (6) | 0.0018 (5) | 0.0027 (5) | 0.0016 (5) |
C10 | 0.0160 (6) | 0.0138 (6) | 0.0145 (6) | 0.0027 (5) | 0.0034 (5) | 0.0058 (5) |
C11 | 0.0152 (6) | 0.0114 (6) | 0.0171 (6) | 0.0000 (5) | 0.0044 (5) | 0.0037 (5) |
S1 | 0.01389 (15) | 0.01446 (15) | 0.01405 (15) | 0.00125 (12) | 0.00305 (12) | 0.00144 (12) |
N1 | 0.0158 (6) | 0.0114 (5) | 0.0165 (6) | 0.0028 (4) | 0.0036 (5) | 0.0031 (4) |
N2 | 0.0140 (5) | 0.0117 (5) | 0.0161 (6) | 0.0008 (4) | 0.0037 (4) | 0.0039 (4) |
C1 | 0.0117 (6) | 0.0133 (6) | 0.0136 (6) | 0.0005 (5) | −0.0006 (5) | 0.0021 (5) |
C2 | 0.0126 (6) | 0.0123 (6) | 0.0156 (6) | 0.0012 (5) | 0.0011 (5) | 0.0042 (5) |
C3 | 0.0112 (6) | 0.0125 (6) | 0.0138 (6) | −0.0012 (5) | 0.0014 (5) | 0.0027 (5) |
C4 | 0.0149 (6) | 0.0121 (6) | 0.0180 (7) | 0.0014 (5) | 0.0020 (5) | 0.0030 (5) |
C5 | 0.0125 (6) | 0.0172 (6) | 0.0152 (6) | 0.0013 (5) | 0.0012 (5) | 0.0017 (5) |
C6 | 0.0168 (6) | 0.0203 (7) | 0.0164 (6) | 0.0014 (5) | 0.0044 (5) | 0.0072 (5) |
C7 | 0.0188 (7) | 0.0165 (6) | 0.0195 (7) | 0.0031 (5) | 0.0035 (6) | 0.0082 (5) |
C8 | 0.0188 (7) | 0.0211 (7) | 0.0209 (7) | 0.0039 (6) | 0.0074 (6) | 0.0019 (6) |
O1 | 0.0289 (6) | 0.0185 (5) | 0.0315 (6) | 0.0046 (5) | 0.0105 (5) | 0.0118 (5) |
I1—C9 | 2.0981 (14) | C3—C4 | 1.3888 (19) |
F1—C10 | 1.3424 (16) | C4—H4 | 0.9500 |
F2—C11 | 1.3452 (16) | C4—C5 | 1.396 (2) |
C9—C10 | 1.3882 (19) | C5—C6 | 1.404 (2) |
C9—C11i | 1.386 (2) | C5—C8 | 1.509 (2) |
C10—C11 | 1.383 (2) | C6—H6 | 0.9500 |
S1—C1 | 1.7035 (15) | C6—C7 | 1.392 (2) |
N1—HN1 | 0.830 (15) | C7—H7 | 0.9500 |
N1—C1 | 1.3542 (19) | C8—H8A | 0.9800 |
N1—C2 | 1.3926 (18) | C8—H8B | 0.9800 |
N2—HN2 | 0.876 (15) | C8—H8C | 0.9800 |
N2—C1 | 1.3557 (18) | O1—H1AO | 0.880 (18) |
N2—C3 | 1.3905 (18) | O1—H1BO | 0.883 (18) |
C2—C3 | 1.3975 (19) | O1—H2O1 | 0.872 (17) |
C2—C7 | 1.387 (2) | ||
C10—C9—I1 | 122.63 (11) | C4—C3—N2 | 131.65 (13) |
C11i—C9—I1 | 120.13 (10) | C4—C3—C2 | 121.84 (13) |
C11i—C9—C10 | 117.17 (13) | C3—C4—H4 | 121.2 |
F1—C10—C9 | 120.35 (13) | C3—C4—C5 | 117.61 (13) |
F1—C10—C11 | 118.48 (12) | C5—C4—H4 | 121.2 |
C11—C10—C9 | 121.15 (13) | C4—C5—C6 | 119.91 (13) |
F2—C11—C9i | 120.02 (13) | C4—C5—C8 | 120.20 (14) |
F2—C11—C10 | 118.29 (13) | C6—C5—C8 | 119.89 (14) |
C10—C11—C9i | 121.68 (13) | C5—C6—H6 | 118.7 |
C1—N1—HN1 | 124.2 (15) | C7—C6—C5 | 122.63 (14) |
C1—N1—C2 | 110.28 (12) | C7—C6—H6 | 118.7 |
C2—N1—HN1 | 125.5 (15) | C2—C7—C6 | 116.72 (14) |
C1—N2—HN2 | 123.8 (14) | C2—C7—H7 | 121.6 |
C1—N2—C3 | 110.09 (12) | C6—C7—H7 | 121.6 |
C3—N2—HN2 | 125.8 (14) | C5—C8—H8A | 109.5 |
N1—C1—S1 | 126.80 (11) | C5—C8—H8B | 109.5 |
N1—C1—N2 | 107.02 (12) | C5—C8—H8C | 109.5 |
N2—C1—S1 | 126.17 (11) | H8A—C8—H8B | 109.5 |
N1—C2—C3 | 106.11 (12) | H8A—C8—H8C | 109.5 |
C7—C2—N1 | 132.60 (13) | H8B—C8—H8C | 109.5 |
C7—C2—C3 | 121.28 (13) | H1AO—O1—H2O1 | 101 (3) |
N2—C3—C2 | 106.49 (12) | H1BO—O1—H2O1 | 101 (3) |
I1—C9—C10—F1 | 1.58 (19) | C1—N2—C3—C4 | −178.92 (15) |
I1—C9—C10—C11 | −176.86 (10) | C2—N1—C1—S1 | −179.80 (11) |
F1—C10—C11—F2 | 0.3 (2) | C2—N1—C1—N2 | −0.27 (16) |
F1—C10—C11—C9i | −178.58 (13) | C2—C3—C4—C5 | 0.7 (2) |
C9—C10—C11—F2 | 178.75 (13) | C3—N2—C1—S1 | 179.96 (11) |
C9—C10—C11—C9i | −0.1 (2) | C3—N2—C1—N1 | 0.44 (16) |
C11i—C9—C10—F1 | 178.54 (12) | C3—C2—C7—C6 | −0.8 (2) |
C11i—C9—C10—C11 | 0.1 (2) | C3—C4—C5—C6 | −0.9 (2) |
N1—C2—C3—N2 | 0.25 (15) | C3—C4—C5—C8 | 178.66 (13) |
N1—C2—C3—C4 | 178.92 (13) | C4—C5—C6—C7 | 0.2 (2) |
N1—C2—C7—C6 | −179.24 (15) | C5—C6—C7—C2 | 0.6 (2) |
N2—C3—C4—C5 | 179.03 (14) | C7—C2—C3—N2 | −178.58 (13) |
C1—N1—C2—C3 | 0.01 (16) | C7—C2—C3—C4 | 0.1 (2) |
C1—N1—C2—C7 | 178.65 (16) | C8—C5—C6—C7 | −179.33 (14) |
C1—N2—C3—C2 | −0.43 (16) |
Symmetry code: (i) −x+2, −y+1, −z+2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—HN1···O1 | 0.83 (2) | 2.06 (2) | 2.8763 (17) | 166 (2) |
N2—HN2···S1ii | 0.88 (2) | 2.57 (2) | 3.4211 (13) | 164 (2) |
C4—H4···I1iii | 0.95 | 3.03 | 3.9505 (14) | 164 |
O1—H1AO···O1iv | 0.88 (2) | 1.85 (2) | 2.708 (3) | 163 (4) |
O1—H1BO···O1v | 0.88 (2) | 1.89 (2) | 2.759 (3) | 167 (4) |
O1—H2O1···I1 | 0.87 (2) | 3.16 (3) | 3.7419 (12) | 126 (2) |
O1—H2O1···S1iv | 0.87 (2) | 2.65 (2) | 3.4251 (13) | 149 (3) |
Symmetry codes: (ii) −x+2, −y+2, −z+1; (iii) x, y+1, z; (iv) −x+2, −y+1, −z+1; (v) −x+1, −y+1, −z+1. |
C6F3I3·C8H8N2S | F(000) = 1232 |
Mr = 673.98 | Dx = 2.613 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 15.191 (2) Å | Cell parameters from 9964 reflections |
b = 5.0074 (7) Å | θ = 2.4–27.5° |
c = 22.715 (3) Å | µ = 5.62 mm−1 |
β = 97.460 (6)° | T = 100 K |
V = 1713.3 (4) Å3 | Needle, colourless |
Z = 4 | 0.26 × 0.04 × 0.04 mm |
Bruker D8 Venture Photon 2 diffractometer | 3039 reflections with I > 2σ(I) |
Radiation source: Incoatec IµS | Rint = 0.069 |
φ and ω scans | θmax = 27.6°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2017) | h = −19→19 |
Tmin = 0.582, Tmax = 0.746 | k = −6→6 |
23258 measured reflections | l = −29→29 |
3971 independent reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.047 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.105 | w = 1/[σ2(Fo2) + 32.9663P] where P = (Fo2 + 2Fc2)/3 |
S = 1.22 | (Δ/σ)max < 0.001 |
3971 reflections | Δρmax = 2.36 e Å−3 |
215 parameters | Δρmin = −1.89 e Å−3 |
1 restraint |
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 | 0.83468 (4) | 0.73539 (12) | 0.22592 (3) | 0.02269 (15) | |
I2 | 1.12973 (3) | 0.55191 (11) | 0.42927 (2) | 0.01871 (14) | |
I3 | 0.78829 (3) | −0.06392 (11) | 0.42073 (2) | 0.01766 (13) | |
F1 | 1.0160 (3) | 0.7879 (10) | 0.3105 (2) | 0.0238 (11) | |
F2 | 0.9829 (3) | 0.1538 (10) | 0.4578 (2) | 0.0217 (11) | |
F3 | 0.7534 (3) | 0.2862 (11) | 0.3013 (2) | 0.0226 (11) | |
C9 | 0.8839 (5) | 0.5360 (16) | 0.3041 (4) | 0.0161 (16) | |
C10 | 0.9672 (5) | 0.5984 (17) | 0.3334 (4) | 0.0166 (17) | |
C11 | 1.0030 (5) | 0.4712 (18) | 0.3850 (4) | 0.0190 (17) | |
C12 | 0.9504 (5) | 0.2824 (17) | 0.4079 (3) | 0.0146 (16) | |
C13 | 0.8652 (5) | 0.2139 (17) | 0.3811 (4) | 0.0178 (17) | |
C14 | 0.8346 (5) | 0.3458 (17) | 0.3285 (4) | 0.0159 (16) | |
S1 | 0.34092 (13) | 1.4956 (4) | 0.50777 (9) | 0.0186 (4) | |
N1 | 0.4563 (5) | 1.2204 (15) | 0.4472 (3) | 0.0196 (15) | |
HN1 | 0.505 (4) | 1.302 (17) | 0.460 (4) | 0.024* | |
N2 | 0.3181 (5) | 1.1018 (15) | 0.4239 (3) | 0.0179 (15) | |
HN2 | 0.264 (7) | 1.10 (2) | 0.427 (4) | 0.021* | |
C1 | 0.3721 (5) | 1.2703 (16) | 0.4592 (4) | 0.0160 (16) | |
C2 | 0.4551 (5) | 1.0249 (17) | 0.4036 (4) | 0.0173 (17) | |
C3 | 0.5223 (6) | 0.9016 (18) | 0.3782 (4) | 0.0206 (18) | |
H3 | 0.582456 | 0.952312 | 0.389046 | 0.025* | |
C4 | 0.5000 (5) | 0.7020 (17) | 0.3364 (4) | 0.0204 (18) | |
C5 | 0.4109 (6) | 0.6252 (18) | 0.3226 (4) | 0.0212 (18) | |
H5 | 0.396802 | 0.484620 | 0.294924 | 0.025* | |
C6 | 0.3427 (6) | 0.7456 (17) | 0.3477 (4) | 0.0187 (17) | |
H6 | 0.282540 | 0.695837 | 0.336564 | 0.022* | |
C7 | 0.3663 (5) | 0.9433 (18) | 0.3902 (4) | 0.0183 (17) | |
C8 | 0.5709 (6) | 0.561 (2) | 0.3080 (4) | 0.027 (2) | |
H8A | 0.588556 | 0.398157 | 0.330193 | 0.041* | |
H8B | 0.622521 | 0.679184 | 0.308275 | 0.041* | |
H8C | 0.547999 | 0.515407 | 0.266904 | 0.041* |
U11 | U22 | U33 | U12 | U13 | U23 | |
I1 | 0.0241 (3) | 0.0236 (3) | 0.0196 (3) | 0.0058 (2) | 0.0002 (2) | 0.0034 (2) |
I2 | 0.0134 (2) | 0.0228 (3) | 0.0198 (3) | −0.0017 (2) | 0.0018 (2) | −0.0022 (2) |
I3 | 0.0150 (2) | 0.0183 (3) | 0.0204 (3) | −0.0014 (2) | 0.0050 (2) | −0.0012 (2) |
F1 | 0.023 (3) | 0.026 (3) | 0.024 (3) | −0.008 (2) | 0.005 (2) | 0.007 (2) |
F2 | 0.017 (2) | 0.027 (3) | 0.019 (3) | 0.000 (2) | −0.001 (2) | 0.005 (2) |
F3 | 0.012 (2) | 0.031 (3) | 0.023 (3) | −0.002 (2) | −0.0043 (19) | 0.000 (2) |
C9 | 0.017 (4) | 0.014 (4) | 0.017 (4) | 0.003 (3) | 0.002 (3) | −0.003 (3) |
C10 | 0.011 (4) | 0.022 (4) | 0.018 (4) | 0.000 (3) | 0.006 (3) | 0.000 (3) |
C11 | 0.015 (4) | 0.024 (5) | 0.017 (4) | 0.002 (3) | −0.001 (3) | −0.003 (3) |
C12 | 0.014 (4) | 0.020 (4) | 0.009 (4) | 0.001 (3) | 0.001 (3) | −0.005 (3) |
C13 | 0.015 (4) | 0.021 (4) | 0.017 (4) | 0.001 (3) | 0.003 (3) | 0.003 (3) |
C14 | 0.012 (4) | 0.018 (4) | 0.017 (4) | 0.000 (3) | 0.001 (3) | −0.002 (3) |
S1 | 0.0153 (9) | 0.0217 (11) | 0.0185 (10) | −0.0007 (8) | 0.0010 (8) | −0.0038 (8) |
N1 | 0.017 (3) | 0.018 (4) | 0.024 (4) | −0.002 (3) | 0.002 (3) | −0.002 (3) |
N2 | 0.010 (3) | 0.021 (4) | 0.022 (4) | 0.001 (3) | 0.001 (3) | −0.003 (3) |
C1 | 0.019 (4) | 0.010 (4) | 0.019 (4) | 0.002 (3) | 0.002 (3) | 0.003 (3) |
C2 | 0.017 (4) | 0.018 (4) | 0.017 (4) | −0.003 (3) | 0.005 (3) | 0.010 (3) |
C3 | 0.016 (4) | 0.021 (4) | 0.026 (5) | −0.003 (3) | 0.008 (3) | 0.003 (4) |
C4 | 0.016 (4) | 0.018 (4) | 0.028 (5) | −0.002 (3) | 0.003 (3) | −0.010 (4) |
C5 | 0.020 (4) | 0.021 (4) | 0.023 (5) | −0.006 (3) | 0.005 (3) | 0.002 (4) |
C6 | 0.017 (4) | 0.019 (4) | 0.019 (4) | −0.002 (3) | 0.001 (3) | 0.000 (3) |
C7 | 0.009 (3) | 0.026 (5) | 0.020 (4) | 0.004 (3) | 0.000 (3) | −0.001 (4) |
C8 | 0.021 (4) | 0.032 (5) | 0.030 (5) | 0.005 (4) | 0.010 (4) | −0.003 (4) |
I1—C9 | 2.089 (8) | N2—HN2 | 0.84 (10) |
I2—C11 | 2.093 (8) | N2—C1 | 1.363 (11) |
I3—C13 | 2.094 (8) | N2—C7 | 1.378 (11) |
F1—C10 | 1.349 (9) | C2—C3 | 1.382 (12) |
F2—C12 | 1.342 (9) | C2—C7 | 1.405 (11) |
F3—C14 | 1.340 (9) | C3—H3 | 0.9500 |
C9—C10 | 1.388 (11) | C3—C4 | 1.390 (12) |
C9—C14 | 1.372 (12) | C4—C5 | 1.402 (11) |
C10—C11 | 1.381 (12) | C4—C8 | 1.500 (12) |
C11—C12 | 1.382 (12) | C5—H5 | 0.9500 |
C12—C13 | 1.399 (11) | C5—C6 | 1.384 (12) |
C13—C14 | 1.391 (11) | C6—H6 | 0.9500 |
S1—C1 | 1.688 (8) | C6—C7 | 1.396 (12) |
N1—HN1 | 0.86 (2) | C8—H8A | 0.9800 |
N1—C1 | 1.365 (11) | C8—H8B | 0.9800 |
N1—C2 | 1.391 (11) | C8—H8C | 0.9800 |
C10—C9—I1 | 120.3 (6) | N2—C1—N1 | 106.1 (7) |
C14—C9—I1 | 121.5 (6) | N1—C2—C7 | 106.4 (7) |
C14—C9—C10 | 118.2 (8) | C3—C2—N1 | 132.1 (8) |
F1—C10—C9 | 119.0 (7) | C3—C2—C7 | 121.3 (8) |
F1—C10—C11 | 118.5 (7) | C2—C3—H3 | 120.7 |
C11—C10—C9 | 122.5 (8) | C2—C3—C4 | 118.7 (8) |
C10—C11—I2 | 123.7 (6) | C4—C3—H3 | 120.7 |
C10—C11—C12 | 116.9 (7) | C3—C4—C5 | 119.4 (8) |
C12—C11—I2 | 119.5 (6) | C3—C4—C8 | 120.4 (8) |
F2—C12—C11 | 118.6 (7) | C5—C4—C8 | 120.1 (8) |
F2—C12—C13 | 117.9 (7) | C4—C5—H5 | 118.6 |
C11—C12—C13 | 123.4 (8) | C6—C5—C4 | 122.8 (8) |
C12—C13—I3 | 120.8 (6) | C6—C5—H5 | 118.6 |
C14—C13—I3 | 122.8 (6) | C5—C6—H6 | 121.5 |
C14—C13—C12 | 116.4 (8) | C5—C6—C7 | 117.1 (8) |
F3—C14—C9 | 119.0 (7) | C7—C6—H6 | 121.5 |
F3—C14—C13 | 118.4 (7) | N2—C7—C2 | 106.1 (7) |
C9—C14—C13 | 122.6 (8) | N2—C7—C6 | 133.3 (7) |
C1—N1—HN1 | 129 (7) | C6—C7—C2 | 120.6 (8) |
C1—N1—C2 | 110.2 (7) | C4—C8—H8A | 109.5 |
C2—N1—HN1 | 120 (7) | C4—C8—H8B | 109.5 |
C1—N2—HN2 | 118 (7) | C4—C8—H8C | 109.5 |
C1—N2—C7 | 111.2 (7) | H8A—C8—H8B | 109.5 |
C7—N2—HN2 | 131 (7) | H8A—C8—H8C | 109.5 |
N1—C1—S1 | 127.0 (6) | H8B—C8—H8C | 109.5 |
N2—C1—S1 | 126.9 (6) | ||
I1—C9—C10—F1 | −0.4 (10) | C14—C9—C10—C11 | 1.9 (13) |
I1—C9—C10—C11 | −179.5 (6) | N1—C2—C3—C4 | 177.5 (9) |
I1—C9—C14—F3 | 0.4 (11) | N1—C2—C7—N2 | 2.9 (9) |
I1—C9—C14—C13 | −178.8 (6) | N1—C2—C7—C6 | −179.7 (8) |
I2—C11—C12—F2 | −0.8 (10) | C1—N1—C2—C3 | −177.6 (9) |
I2—C11—C12—C13 | −179.5 (6) | C1—N1—C2—C7 | −2.6 (9) |
I3—C13—C14—F3 | −2.0 (11) | C1—N2—C7—C2 | −2.3 (10) |
I3—C13—C14—C9 | 177.2 (6) | C1—N2—C7—C6 | −179.2 (9) |
F1—C10—C11—I2 | −0.8 (11) | C2—N1—C1—S1 | −178.7 (6) |
F1—C10—C11—C12 | 178.6 (7) | C2—N1—C1—N2 | 1.2 (9) |
F2—C12—C13—I3 | 3.6 (10) | C2—C3—C4—C5 | −2.1 (13) |
F2—C12—C13—C14 | −178.2 (7) | C2—C3—C4—C8 | −179.5 (8) |
C9—C10—C11—I2 | 178.3 (6) | C3—C2—C7—N2 | 178.5 (8) |
C9—C10—C11—C12 | −2.3 (13) | C3—C2—C7—C6 | −4.0 (13) |
C10—C9—C14—F3 | 179.0 (7) | C3—C4—C5—C6 | 2.0 (14) |
C10—C9—C14—C13 | −0.2 (13) | C4—C5—C6—C7 | −2.7 (13) |
C10—C11—C12—F2 | 179.8 (7) | C5—C6—C7—N2 | −179.7 (9) |
C10—C11—C12—C13 | 1.1 (13) | C5—C6—C7—C2 | 3.7 (13) |
C11—C12—C13—I3 | −177.6 (6) | C7—N2—C1—S1 | −179.4 (6) |
C11—C12—C13—C14 | 0.5 (12) | C7—N2—C1—N1 | 0.7 (10) |
C12—C13—C14—F3 | 179.9 (7) | C7—C2—C3—C4 | 3.1 (13) |
C12—C13—C14—C9 | −0.9 (12) | C8—C4—C5—C6 | 179.4 (9) |
C14—C9—C10—F1 | −179.0 (7) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—HN1···S1i | 0.86 (2) | 2.57 (2) | 3.427 (7) | 174 (9) |
N2—HN2···I2ii | 0.84 (10) | 3.03 (10) | 3.657 (7) | 133 (8) |
C3—H3···I3iii | 0.95 | 3.12 | 4.035 (9) | 163 |
C6—H6···I1iv | 0.95 | 3.14 | 3.927 (8) | 142 |
Symmetry codes: (i) −x+1, −y+3, −z+1; (ii) x−1, y+1, z; (iii) x, y+1, z; (iv) −x+1, y−1/2, −z+1/2. |
C6F4I2·C7H5NOS | F(000) = 1024 |
Mr = 553.04 | Dx = 2.407 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 13.7789 (12) Å | Cell parameters from 5954 reflections |
b = 4.4129 (4) Å | θ = 3.0–26.8° |
c = 25.252 (2) Å | µ = 4.30 mm−1 |
β = 96.337 (3)° | T = 100 K |
V = 1526.0 (2) Å3 | Needle, colourless |
Z = 4 | 0.46 × 0.06 × 0.02 mm |
Bruker D8 Venture Photon 2 diffractometer | 2510 reflections with I > 2σ(I) |
Radiation source: Incoatec IµS | Rint = 0.066 |
φ and ω scans | θmax = 26.8°, θmin = 3.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2017) | h = −17→17 |
Tmin = 0.578, Tmax = 0.745 | k = −5→5 |
12498 measured reflections | l = −31→31 |
3210 independent reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.047 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.087 | w = 1/[σ2(Fo2) + (0.0191P)2 + 7.3427P] where P = (Fo2 + 2Fc2)/3 |
S = 1.11 | (Δ/σ)max = 0.001 |
3210 reflections | Δρmax = 1.58 e Å−3 |
203 parameters | Δρmin = −1.52 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 | 0.30796 (3) | −0.08467 (10) | 0.67864 (2) | 0.02151 (14) | |
I2 | 0.44314 (3) | −0.05194 (10) | 0.81380 (2) | 0.01770 (13) | |
F1 | 0.6245 (3) | 0.3640 (9) | 0.80387 (17) | 0.0263 (10) | |
F2 | 0.6876 (3) | 0.6765 (10) | 0.7230 (2) | 0.0339 (11) | |
F3 | 0.5903 (3) | 0.6411 (10) | 0.62370 (19) | 0.0350 (11) | |
F4 | 0.4320 (3) | 0.2897 (10) | 0.60463 (17) | 0.0298 (10) | |
C8 | 0.4399 (5) | 0.1468 (15) | 0.6957 (3) | 0.0158 (15) | |
C9 | 0.4896 (5) | 0.1682 (14) | 0.7472 (3) | 0.0158 (15) | |
C10 | 0.5749 (5) | 0.3417 (15) | 0.7561 (3) | 0.0180 (16) | |
C11 | 0.6078 (5) | 0.4963 (15) | 0.7141 (3) | 0.0250 (17) | |
C12 | 0.5583 (6) | 0.4836 (16) | 0.6629 (3) | 0.0273 (18) | |
C13 | 0.4767 (5) | 0.3023 (16) | 0.6542 (3) | 0.0209 (16) | |
S1 | 0.07783 (13) | 0.0388 (4) | 0.57938 (7) | 0.0193 (4) | |
O1 | 0.2157 (3) | 0.4196 (10) | 0.55679 (19) | 0.0193 (11) | |
N1 | 0.1100 (4) | 0.3227 (13) | 0.4874 (2) | 0.0152 (13) | |
HN1 | 0.068 (6) | 0.228 (18) | 0.466 (3) | 0.03 (2)* | |
C1 | 0.1325 (5) | 0.2629 (14) | 0.5389 (3) | 0.0147 (14) | |
C2 | 0.1772 (5) | 0.5252 (15) | 0.4695 (3) | 0.0158 (14) | |
C3 | 0.1868 (5) | 0.6569 (16) | 0.4216 (3) | 0.0219 (16) | |
H3 | 0.141810 | 0.617405 | 0.391053 | 0.026* | |
C4 | 0.2659 (5) | 0.8527 (15) | 0.4193 (3) | 0.0212 (16) | |
H4 | 0.274897 | 0.948201 | 0.386523 | 0.025* | |
C5 | 0.3316 (6) | 0.9111 (16) | 0.4637 (3) | 0.0229 (16) | |
H5 | 0.384448 | 1.045851 | 0.460649 | 0.028* | |
C6 | 0.3218 (5) | 0.7761 (15) | 0.5130 (3) | 0.0193 (16) | |
H6 | 0.366596 | 0.813408 | 0.543631 | 0.023* | |
C7 | 0.2429 (5) | 0.5852 (14) | 0.5140 (3) | 0.0142 (14) |
U11 | U22 | U33 | U12 | U13 | U23 | |
I1 | 0.0210 (3) | 0.0213 (2) | 0.0210 (3) | −0.0009 (2) | −0.0034 (2) | −0.0037 (2) |
I2 | 0.0223 (2) | 0.0177 (2) | 0.0130 (2) | 0.0024 (2) | 0.00165 (18) | −0.00026 (18) |
F1 | 0.018 (2) | 0.031 (2) | 0.027 (3) | 0.0013 (18) | −0.0068 (18) | −0.0058 (19) |
F2 | 0.021 (2) | 0.029 (2) | 0.052 (3) | −0.0102 (19) | 0.010 (2) | −0.003 (2) |
F3 | 0.043 (3) | 0.027 (2) | 0.039 (3) | −0.001 (2) | 0.020 (2) | 0.012 (2) |
F4 | 0.041 (3) | 0.032 (2) | 0.015 (2) | 0.005 (2) | −0.001 (2) | 0.0042 (19) |
C8 | 0.011 (3) | 0.021 (3) | 0.016 (4) | 0.005 (3) | 0.004 (3) | −0.003 (3) |
C9 | 0.016 (3) | 0.013 (3) | 0.020 (4) | 0.005 (3) | 0.007 (3) | 0.002 (3) |
C10 | 0.016 (4) | 0.015 (3) | 0.023 (4) | 0.004 (3) | −0.001 (3) | −0.006 (3) |
C11 | 0.024 (4) | 0.014 (4) | 0.038 (5) | 0.002 (3) | 0.010 (4) | −0.002 (3) |
C12 | 0.037 (5) | 0.021 (4) | 0.027 (4) | 0.005 (3) | 0.019 (4) | 0.013 (3) |
C13 | 0.027 (4) | 0.020 (3) | 0.016 (4) | 0.010 (3) | 0.001 (3) | 0.006 (3) |
S1 | 0.0249 (9) | 0.0194 (9) | 0.0132 (9) | −0.0053 (7) | 0.0007 (7) | 0.0000 (7) |
O1 | 0.023 (3) | 0.017 (2) | 0.017 (3) | 0.000 (2) | −0.003 (2) | 0.003 (2) |
N1 | 0.021 (3) | 0.013 (3) | 0.010 (3) | 0.000 (2) | −0.002 (3) | −0.003 (2) |
C1 | 0.013 (3) | 0.012 (3) | 0.019 (4) | 0.004 (3) | 0.003 (3) | −0.002 (3) |
C2 | 0.021 (4) | 0.016 (3) | 0.011 (4) | 0.000 (3) | 0.004 (3) | −0.002 (3) |
C3 | 0.026 (4) | 0.021 (4) | 0.018 (4) | 0.000 (3) | 0.000 (3) | −0.009 (3) |
C4 | 0.029 (4) | 0.016 (3) | 0.019 (4) | 0.002 (3) | 0.005 (3) | 0.004 (3) |
C5 | 0.029 (4) | 0.018 (4) | 0.022 (4) | 0.000 (3) | 0.008 (3) | 0.008 (3) |
C6 | 0.017 (4) | 0.018 (4) | 0.021 (4) | −0.002 (3) | −0.003 (3) | −0.003 (3) |
C7 | 0.022 (4) | 0.012 (3) | 0.010 (3) | −0.003 (3) | 0.005 (3) | −0.002 (3) |
I1—C8 | 2.088 (7) | O1—C7 | 1.390 (8) |
I2—C9 | 2.101 (7) | N1—HN1 | 0.85 (8) |
F1—C10 | 1.322 (8) | N1—C1 | 1.330 (9) |
F2—C11 | 1.355 (8) | N1—C2 | 1.396 (9) |
F3—C12 | 1.323 (8) | C2—C3 | 1.364 (10) |
F4—C13 | 1.333 (8) | C2—C7 | 1.387 (9) |
C8—C9 | 1.406 (10) | C3—H3 | 0.9500 |
C8—C13 | 1.394 (10) | C3—C4 | 1.397 (10) |
C9—C10 | 1.400 (9) | C4—H4 | 0.9500 |
C10—C11 | 1.380 (11) | C4—C5 | 1.385 (10) |
C11—C12 | 1.396 (11) | C5—H5 | 0.9500 |
C12—C13 | 1.378 (11) | C5—C6 | 1.399 (10) |
S1—C1 | 1.662 (7) | C6—H6 | 0.9500 |
O1—C1 | 1.372 (8) | C6—C7 | 1.378 (9) |
C9—C8—I1 | 123.2 (5) | O1—C1—S1 | 121.1 (5) |
C13—C8—I1 | 117.8 (5) | N1—C1—S1 | 130.3 (5) |
C13—C8—C9 | 118.9 (6) | N1—C1—O1 | 108.6 (6) |
C8—C9—I2 | 123.3 (5) | C3—C2—N1 | 133.8 (6) |
C10—C9—I2 | 116.7 (5) | C3—C2—C7 | 121.2 (6) |
C10—C9—C8 | 120.0 (6) | C7—C2—N1 | 104.9 (6) |
F1—C10—C9 | 121.8 (7) | C2—C3—H3 | 121.6 |
F1—C10—C11 | 118.9 (6) | C2—C3—C4 | 116.9 (6) |
C11—C10—C9 | 119.3 (7) | C4—C3—H3 | 121.6 |
F2—C11—C10 | 119.5 (7) | C3—C4—H4 | 119.1 |
F2—C11—C12 | 118.9 (7) | C5—C4—C3 | 121.7 (7) |
C10—C11—C12 | 121.6 (7) | C5—C4—H4 | 119.1 |
F3—C12—C11 | 120.2 (7) | C4—C5—H5 | 119.3 |
F3—C12—C13 | 121.2 (7) | C4—C5—C6 | 121.4 (7) |
C13—C12—C11 | 118.6 (7) | C6—C5—H5 | 119.3 |
F4—C13—C8 | 121.1 (6) | C5—C6—H6 | 122.2 |
F4—C13—C12 | 117.3 (7) | C7—C6—C5 | 115.5 (6) |
C12—C13—C8 | 121.5 (7) | C7—C6—H6 | 122.2 |
C1—O1—C7 | 107.2 (5) | C2—C7—O1 | 108.7 (5) |
C1—N1—HN1 | 126 (6) | C6—C7—O1 | 128.1 (6) |
C1—N1—C2 | 110.5 (6) | C6—C7—C2 | 123.2 (6) |
C2—N1—HN1 | 123 (6) | ||
I1—C8—C9—I2 | 4.0 (8) | C13—C8—C9—I2 | 179.9 (5) |
I1—C8—C9—C10 | −176.3 (5) | C13—C8—C9—C10 | −0.5 (10) |
I1—C8—C13—F4 | −3.7 (9) | N1—C2—C3—C4 | −179.9 (7) |
I1—C8—C13—C12 | 173.9 (5) | N1—C2—C7—O1 | 0.7 (7) |
I2—C9—C10—F1 | 0.7 (8) | N1—C2—C7—C6 | 179.5 (6) |
I2—C9—C10—C11 | −178.7 (5) | C1—O1—C7—C2 | −1.1 (7) |
F1—C10—C11—F2 | −2.7 (10) | C1—O1—C7—C6 | −180.0 (7) |
F1—C10—C11—C12 | −179.5 (6) | C1—N1—C2—C3 | −179.7 (7) |
F2—C11—C12—F3 | 1.3 (10) | C1—N1—C2—C7 | 0.1 (7) |
F2—C11—C12—C13 | −179.3 (6) | C2—N1—C1—S1 | −179.8 (5) |
F3—C12—C13—F4 | 0.7 (10) | C2—N1—C1—O1 | −0.8 (7) |
F3—C12—C13—C8 | −177.0 (6) | C2—C3—C4—C5 | −0.1 (10) |
C8—C9—C10—F1 | −179.0 (6) | C3—C2—C7—O1 | −179.6 (6) |
C8—C9—C10—C11 | 1.6 (10) | C3—C2—C7—C6 | −0.7 (11) |
C9—C8—C13—F4 | −179.8 (6) | C3—C4—C5—C6 | 0.1 (11) |
C9—C8—C13—C12 | −2.2 (10) | C4—C5—C6—C7 | −0.4 (10) |
C9—C10—C11—F2 | 176.7 (6) | C5—C6—C7—O1 | 179.3 (6) |
C9—C10—C11—C12 | −0.1 (10) | C5—C6—C7—C2 | 0.7 (10) |
C10—C11—C12—F3 | 178.1 (6) | C7—O1—C1—S1 | −179.7 (5) |
C10—C11—C12—C13 | −2.5 (11) | C7—O1—C1—N1 | 1.2 (7) |
C11—C12—C13—F4 | −178.7 (6) | C7—C2—C3—C4 | 0.3 (10) |
C11—C12—C13—C8 | 3.7 (11) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—HN1···S1i | 0.85 (8) | 2.50 (8) | 3.335 (6) | 167 (8) |
C3—H3···I2ii | 0.95 | 3.19 | 4.108 (7) | 162 |
Symmetry codes: (i) −x, −y, −z+1; (ii) x−1/2, −y+1/2, z−1/2. |
C6F4I2·C7H5NOS | F(000) = 1024 |
Mr = 553.04 | Dx = 2.437 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 15.1655 (8) Å | Cell parameters from 9330 reflections |
b = 4.3803 (2) Å | θ = 2.7–30.6° |
c = 23.0358 (12) Å | µ = 4.35 mm−1 |
β = 99.923 (2)° | T = 100 K |
V = 1507.36 (13) Å3 | Needle, colourless |
Z = 4 | 0.23 × 0.12 × 0.09 mm |
Bruker D8 Venture Photon 2 diffractometer | 4119 reflections with I > 2σ(I) |
Radiation source: Incoatec IµS | Rint = 0.042 |
φ and ω scans | θmax = 30.6°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2017) | h = −21→21 |
Tmin = 0.541, Tmax = 0.746 | k = −6→6 |
39610 measured reflections | l = −32→32 |
4625 independent reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.022 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.048 | w = 1/[σ2(Fo2) + (0.0088P)2 + 2.2764P] where P = (Fo2 + 2Fc2)/3 |
S = 1.16 | (Δ/σ)max = 0.002 |
4625 reflections | Δρmax = 0.96 e Å−3 |
203 parameters | Δρmin = −1.35 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 | 0.71955 (2) | −0.00881 (3) | 0.06483 (2) | 0.01983 (4) | |
I2 | 0.36910 (2) | 0.55990 (4) | 0.09449 (2) | 0.02789 (5) | |
F1 | 0.51550 (9) | 0.1796 (3) | 0.04571 (6) | 0.0245 (3) | |
F2 | 0.50261 (12) | 0.8071 (4) | 0.20979 (7) | 0.0336 (4) | |
F3 | 0.67787 (12) | 0.7060 (4) | 0.24932 (7) | 0.0422 (4) | |
F4 | 0.77333 (10) | 0.3490 (4) | 0.18773 (7) | 0.0352 (4) | |
C8 | 0.64548 (14) | 0.2498 (5) | 0.11554 (10) | 0.0173 (4) | |
C9 | 0.55516 (14) | 0.3056 (5) | 0.09648 (10) | 0.0171 (4) | |
C10 | 0.50419 (15) | 0.4888 (5) | 0.12703 (10) | 0.0187 (4) | |
C11 | 0.54714 (17) | 0.6213 (5) | 0.17885 (11) | 0.0223 (5) | |
C12 | 0.63676 (18) | 0.5704 (6) | 0.19943 (10) | 0.0250 (5) | |
C13 | 0.68526 (16) | 0.3866 (6) | 0.16770 (11) | 0.0226 (5) | |
S1 | 0.85453 (4) | 0.94524 (12) | 0.49409 (2) | 0.01660 (10) | |
O1 | 0.82568 (10) | 0.5576 (3) | 0.40484 (7) | 0.0155 (3) | |
N1 | 0.96873 (12) | 0.6582 (4) | 0.43253 (8) | 0.0150 (3) | |
HN1 | 1.0171 (19) | 0.742 (7) | 0.4529 (13) | 0.024 (7)* | |
C1 | 0.88629 (14) | 0.7182 (5) | 0.44345 (9) | 0.0151 (4) | |
C2 | 0.96367 (14) | 0.4504 (5) | 0.38611 (9) | 0.0140 (4) | |
C3 | 1.02660 (14) | 0.3138 (5) | 0.35766 (10) | 0.0173 (4) | |
H3 | 1.088760 | 0.354870 | 0.368581 | 0.021* | |
C4 | 0.99394 (15) | 0.1129 (5) | 0.31216 (10) | 0.0176 (4) | |
H4 | 1.035003 | 0.013545 | 0.291629 | 0.021* | |
C5 | 0.90240 (15) | 0.0533 (5) | 0.29583 (10) | 0.0182 (4) | |
H5 | 0.882849 | −0.085313 | 0.264531 | 0.022* | |
C6 | 0.83913 (14) | 0.1930 (5) | 0.32450 (10) | 0.0177 (4) | |
H6 | 0.776786 | 0.154860 | 0.313733 | 0.021* | |
C7 | 0.87317 (14) | 0.3897 (5) | 0.36943 (9) | 0.0141 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
I1 | 0.01738 (7) | 0.02028 (7) | 0.02311 (8) | 0.00339 (5) | 0.00709 (5) | 0.00604 (5) |
I2 | 0.01897 (8) | 0.03084 (9) | 0.03563 (10) | 0.00756 (6) | 0.00974 (6) | 0.00672 (7) |
F1 | 0.0175 (6) | 0.0307 (8) | 0.0242 (7) | −0.0014 (5) | 0.0005 (5) | −0.0107 (6) |
F2 | 0.0534 (10) | 0.0242 (8) | 0.0266 (8) | 0.0077 (7) | 0.0170 (7) | −0.0037 (6) |
F3 | 0.0559 (11) | 0.0436 (10) | 0.0218 (8) | −0.0054 (8) | −0.0080 (7) | −0.0099 (7) |
F4 | 0.0236 (7) | 0.0491 (10) | 0.0282 (8) | 0.0008 (7) | −0.0088 (6) | 0.0030 (7) |
C8 | 0.0163 (9) | 0.0162 (10) | 0.0195 (11) | 0.0003 (8) | 0.0035 (8) | 0.0023 (8) |
C9 | 0.0185 (10) | 0.0153 (9) | 0.0174 (10) | −0.0022 (8) | 0.0031 (8) | 0.0011 (8) |
C10 | 0.0191 (10) | 0.0166 (10) | 0.0217 (11) | 0.0012 (8) | 0.0069 (8) | 0.0039 (8) |
C11 | 0.0341 (13) | 0.0159 (10) | 0.0188 (11) | 0.0031 (9) | 0.0098 (9) | 0.0012 (8) |
C12 | 0.0371 (14) | 0.0225 (11) | 0.0132 (10) | −0.0046 (10) | −0.0017 (9) | −0.0004 (9) |
C13 | 0.0211 (11) | 0.0260 (12) | 0.0188 (11) | −0.0016 (9) | −0.0023 (9) | 0.0068 (9) |
S1 | 0.0159 (2) | 0.0171 (2) | 0.0175 (2) | −0.00208 (18) | 0.00487 (19) | −0.00332 (19) |
O1 | 0.0127 (7) | 0.0170 (7) | 0.0166 (7) | −0.0007 (5) | 0.0023 (6) | −0.0018 (6) |
N1 | 0.0138 (8) | 0.0160 (8) | 0.0150 (9) | −0.0025 (6) | 0.0022 (6) | −0.0024 (7) |
C1 | 0.0147 (9) | 0.0138 (9) | 0.0159 (10) | −0.0011 (7) | 0.0005 (7) | 0.0027 (7) |
C2 | 0.0148 (9) | 0.0123 (9) | 0.0144 (9) | −0.0004 (7) | 0.0015 (7) | 0.0013 (7) |
C3 | 0.0149 (9) | 0.0189 (10) | 0.0184 (10) | 0.0007 (8) | 0.0037 (8) | 0.0027 (8) |
C4 | 0.0205 (10) | 0.0166 (10) | 0.0166 (10) | 0.0019 (8) | 0.0059 (8) | 0.0020 (8) |
C5 | 0.0228 (10) | 0.0173 (10) | 0.0147 (10) | −0.0019 (8) | 0.0034 (8) | 0.0000 (8) |
C6 | 0.0153 (9) | 0.0180 (10) | 0.0187 (11) | −0.0032 (8) | −0.0005 (8) | −0.0010 (8) |
C7 | 0.0151 (9) | 0.0144 (9) | 0.0134 (9) | 0.0007 (7) | 0.0038 (7) | 0.0016 (7) |
I1—C8 | 2.089 (2) | O1—C7 | 1.389 (3) |
I2—C10 | 2.080 (2) | N1—HN1 | 0.88 (3) |
F1—C9 | 1.339 (3) | N1—C1 | 1.343 (3) |
F2—C11 | 1.339 (3) | N1—C2 | 1.396 (3) |
F3—C12 | 1.347 (3) | C2—C3 | 1.383 (3) |
F4—C13 | 1.346 (3) | C2—C7 | 1.386 (3) |
C8—C9 | 1.386 (3) | C3—H3 | 0.9500 |
C8—C13 | 1.384 (3) | C3—C4 | 1.393 (3) |
C9—C10 | 1.387 (3) | C4—H4 | 0.9500 |
C10—C11 | 1.385 (3) | C4—C5 | 1.399 (3) |
C11—C12 | 1.378 (4) | C5—H5 | 0.9500 |
C12—C13 | 1.382 (4) | C5—C6 | 1.396 (3) |
S1—C1 | 1.666 (2) | C6—H6 | 0.9500 |
O1—C1 | 1.360 (2) | C6—C7 | 1.377 (3) |
C9—C8—I1 | 121.04 (17) | O1—C1—S1 | 121.49 (15) |
C13—C8—I1 | 121.61 (17) | N1—C1—S1 | 129.70 (17) |
C13—C8—C9 | 117.2 (2) | N1—C1—O1 | 108.82 (18) |
F1—C9—C8 | 118.4 (2) | C3—C2—N1 | 133.9 (2) |
F1—C9—C10 | 118.4 (2) | C3—C2—C7 | 121.1 (2) |
C8—C9—C10 | 123.2 (2) | C7—C2—N1 | 104.99 (18) |
C9—C10—I2 | 120.27 (17) | C2—C3—H3 | 121.8 |
C11—C10—I2 | 122.39 (17) | C2—C3—C4 | 116.4 (2) |
C11—C10—C9 | 117.3 (2) | C4—C3—H3 | 121.8 |
F2—C11—C10 | 120.5 (2) | C3—C4—H4 | 119.1 |
F2—C11—C12 | 118.2 (2) | C3—C4—C5 | 121.9 (2) |
C12—C11—C10 | 121.2 (2) | C5—C4—H4 | 119.1 |
F3—C12—C11 | 120.4 (2) | C4—C5—H5 | 119.3 |
F3—C12—C13 | 119.9 (2) | C6—C5—C4 | 121.5 (2) |
C11—C12—C13 | 119.7 (2) | C6—C5—H5 | 119.3 |
F4—C13—C8 | 120.2 (2) | C5—C6—H6 | 122.2 |
F4—C13—C12 | 118.5 (2) | C7—C6—C5 | 115.5 (2) |
C12—C13—C8 | 121.3 (2) | C7—C6—H6 | 122.2 |
C1—O1—C7 | 107.32 (16) | C2—C7—O1 | 108.94 (18) |
C1—N1—HN1 | 122.5 (19) | C6—C7—O1 | 127.43 (19) |
C1—N1—C2 | 109.92 (18) | C6—C7—C2 | 123.6 (2) |
C2—N1—HN1 | 127.6 (19) | ||
I1—C8—C9—F1 | 2.6 (3) | C13—C8—C9—F1 | 179.0 (2) |
I1—C8—C9—C10 | −176.56 (17) | C13—C8—C9—C10 | −0.1 (3) |
I1—C8—C13—F4 | −1.6 (3) | N1—C2—C3—C4 | 179.9 (2) |
I1—C8—C13—C12 | 176.58 (18) | N1—C2—C7—O1 | 0.2 (2) |
I2—C10—C11—F2 | −1.1 (3) | N1—C2—C7—C6 | −180.0 (2) |
I2—C10—C11—C12 | 180.00 (18) | C1—O1—C7—C2 | −0.6 (2) |
F1—C9—C10—I2 | 0.6 (3) | C1—O1—C7—C6 | 179.6 (2) |
F1—C9—C10—C11 | −178.8 (2) | C1—N1—C2—C3 | −179.9 (2) |
F2—C11—C12—F3 | −0.2 (3) | C1—N1—C2—C7 | 0.3 (2) |
F2—C11—C12—C13 | −178.2 (2) | C2—N1—C1—S1 | 179.30 (17) |
F3—C12—C13—F4 | −0.3 (4) | C2—N1—C1—O1 | −0.7 (2) |
F3—C12—C13—C8 | −178.4 (2) | C2—C3—C4—C5 | 0.3 (3) |
C8—C9—C10—I2 | 179.72 (17) | C3—C2—C7—O1 | −179.62 (19) |
C8—C9—C10—C11 | 0.3 (3) | C3—C2—C7—C6 | 0.2 (3) |
C9—C8—C13—F4 | −178.0 (2) | C3—C4—C5—C6 | 0.0 (3) |
C9—C8—C13—C12 | 0.1 (3) | C4—C5—C6—C7 | −0.2 (3) |
C9—C10—C11—F2 | 178.3 (2) | C5—C6—C7—O1 | 179.9 (2) |
C9—C10—C11—C12 | −0.6 (3) | C5—C6—C7—C2 | 0.1 (3) |
C10—C11—C12—F3 | 178.7 (2) | C7—O1—C1—S1 | −179.20 (15) |
C10—C11—C12—C13 | 0.7 (4) | C7—O1—C1—N1 | 0.8 (2) |
C11—C12—C13—F4 | 177.8 (2) | C7—C2—C3—C4 | −0.4 (3) |
C11—C12—C13—C8 | −0.4 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—HN1···S1i | 0.88 (3) | 2.52 (3) | 3.3906 (19) | 172 (3) |
C3—H3···I1ii | 0.95 | 3.10 | 4.030 (2) | 166 |
Symmetry codes: (i) −x+2, −y+2, −z+1; (ii) −x+2, y+1/2, −z+1/2. |
C6F4I2·2C7H5NOS | F(000) = 1336 |
Mr = 704.22 | Dx = 2.013 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 31.025 (4) Å | Cell parameters from 9971 reflections |
b = 4.3159 (5) Å | θ = 2.4–28.7° |
c = 19.061 (2) Å | µ = 2.94 mm−1 |
β = 114.434 (4)° | T = 100 K |
V = 2323.6 (5) Å3 | Tabular, colourless |
Z = 4 | 0.29 × 0.12 × 0.03 mm |
Bruker D8 Venture Photon 2 diffractometer | 2571 reflections with I > 2σ(I) |
Radiation source: Incoatec IµS | Rint = 0.047 |
φ and ω scans | θmax = 28.7°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2017) | h = −41→41 |
Tmin = 0.637, Tmax = 0.746 | k = −5→5 |
25197 measured reflections | l = −25→25 |
2950 independent reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.028 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.060 | w = 1/[σ2(Fo2) + 11.7646P] where P = (Fo2 + 2Fc2)/3 |
S = 1.32 | (Δ/σ)max = 0.002 |
2950 reflections | Δρmax = 1.54 e Å−3 |
149 parameters | Δρmin = −1.15 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 | 0.64136 (2) | 0.39079 (5) | 0.46092 (2) | 0.01937 (7) | |
F1 | 0.71102 (7) | 0.7954 (5) | 0.60381 (11) | 0.0276 (5) | |
F2 | 0.70741 (7) | 0.4164 (5) | 0.36823 (11) | 0.0273 (5) | |
C8 | 0.70659 (11) | 0.6029 (8) | 0.48500 (19) | 0.0189 (6) | |
C9 | 0.72975 (11) | 0.7707 (8) | 0.55172 (19) | 0.0194 (7) | |
C10 | 0.72770 (12) | 0.5825 (8) | 0.43364 (19) | 0.0201 (7) | |
S1 | 0.54594 (3) | 0.0194 (2) | 0.43700 (5) | 0.01964 (17) | |
O1 | 0.49241 (8) | 0.4059 (5) | 0.32770 (12) | 0.0181 (5) | |
N1 | 0.46292 (10) | 0.3062 (7) | 0.41195 (16) | 0.0180 (6) | |
HN1 | 0.4609 (14) | 0.224 (10) | 0.452 (2) | 0.028 (11)* | |
C1 | 0.49912 (12) | 0.2491 (8) | 0.39283 (18) | 0.0182 (6) | |
C2 | 0.43102 (12) | 0.5092 (8) | 0.35848 (18) | 0.0187 (6) | |
C3 | 0.38827 (12) | 0.6362 (8) | 0.35038 (19) | 0.0227 (7) | |
H3 | 0.374567 | 0.592471 | 0.385578 | 0.027* | |
C4 | 0.36660 (12) | 0.8320 (8) | 0.2875 (2) | 0.0253 (7) | |
H4 | 0.337264 | 0.925746 | 0.279739 | 0.030* | |
C5 | 0.38649 (13) | 0.8950 (8) | 0.2355 (2) | 0.0251 (7) | |
H5 | 0.370406 | 1.030939 | 0.193581 | 0.030* | |
C6 | 0.42930 (12) | 0.7643 (8) | 0.24340 (19) | 0.0224 (7) | |
H6 | 0.443055 | 0.805267 | 0.208135 | 0.027* | |
C7 | 0.45026 (11) | 0.5714 (7) | 0.30592 (18) | 0.0181 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
I1 | 0.01700 (11) | 0.01887 (11) | 0.02288 (11) | −0.00041 (8) | 0.00889 (8) | 0.00070 (8) |
F1 | 0.0248 (10) | 0.0379 (12) | 0.0253 (10) | −0.0054 (9) | 0.0154 (9) | −0.0045 (9) |
F2 | 0.0246 (10) | 0.0342 (12) | 0.0238 (10) | −0.0064 (9) | 0.0107 (9) | −0.0095 (9) |
C8 | 0.0180 (15) | 0.0161 (15) | 0.0231 (16) | −0.0009 (12) | 0.0092 (13) | 0.0014 (13) |
C9 | 0.0178 (15) | 0.0229 (17) | 0.0198 (16) | 0.0016 (13) | 0.0101 (13) | 0.0002 (13) |
C10 | 0.0196 (16) | 0.0197 (16) | 0.0190 (15) | 0.0010 (13) | 0.0061 (13) | −0.0027 (13) |
S1 | 0.0185 (4) | 0.0201 (4) | 0.0209 (4) | −0.0009 (3) | 0.0089 (3) | 0.0015 (3) |
O1 | 0.0198 (11) | 0.0198 (12) | 0.0159 (10) | −0.0014 (9) | 0.0087 (9) | 0.0002 (9) |
N1 | 0.0202 (14) | 0.0190 (14) | 0.0166 (13) | 0.0002 (11) | 0.0092 (11) | 0.0030 (11) |
C1 | 0.0217 (16) | 0.0163 (16) | 0.0172 (15) | −0.0055 (13) | 0.0085 (13) | −0.0038 (12) |
C2 | 0.0239 (17) | 0.0140 (15) | 0.0164 (15) | −0.0035 (13) | 0.0064 (13) | −0.0009 (12) |
C3 | 0.0219 (16) | 0.0246 (18) | 0.0220 (16) | 0.0004 (14) | 0.0094 (14) | −0.0018 (14) |
C4 | 0.0212 (17) | 0.0241 (19) | 0.0289 (18) | −0.0004 (14) | 0.0088 (15) | −0.0016 (15) |
C5 | 0.0274 (18) | 0.0215 (17) | 0.0206 (16) | −0.0003 (15) | 0.0041 (14) | 0.0016 (14) |
C6 | 0.0274 (18) | 0.0226 (18) | 0.0174 (16) | −0.0048 (14) | 0.0097 (14) | 0.0001 (13) |
C7 | 0.0185 (15) | 0.0158 (16) | 0.0194 (15) | −0.0034 (12) | 0.0073 (13) | −0.0026 (12) |
I1—C8 | 2.092 (3) | N1—C2 | 1.397 (4) |
F1—C9 | 1.346 (4) | C2—C3 | 1.383 (5) |
F2—C10 | 1.347 (4) | C2—C7 | 1.388 (4) |
C8—C9 | 1.379 (5) | C3—H3 | 0.9500 |
C8—C10 | 1.388 (4) | C3—C4 | 1.391 (5) |
C9—C10i | 1.385 (5) | C4—H4 | 0.9500 |
S1—C1 | 1.670 (3) | C4—C5 | 1.393 (5) |
O1—C1 | 1.352 (4) | C5—H5 | 0.9500 |
O1—C7 | 1.394 (4) | C5—C6 | 1.393 (5) |
N1—HN1 | 0.87 (4) | C6—H6 | 0.9500 |
N1—C1 | 1.339 (4) | C6—C7 | 1.376 (5) |
C9—C8—I1 | 121.3 (2) | C3—C2—C7 | 121.4 (3) |
C9—C8—C10 | 117.8 (3) | C7—C2—N1 | 105.2 (3) |
C10—C8—I1 | 120.9 (2) | C2—C3—H3 | 122.1 |
F1—C9—C8 | 120.2 (3) | C2—C3—C4 | 115.9 (3) |
F1—C9—C10i | 118.8 (3) | C4—C3—H3 | 122.1 |
C8—C9—C10i | 121.1 (3) | C3—C4—H4 | 118.9 |
F2—C10—C8 | 120.7 (3) | C3—C4—C5 | 122.2 (3) |
F2—C10—C9i | 118.1 (3) | C5—C4—H4 | 118.9 |
C9i—C10—C8 | 121.2 (3) | C4—C5—H5 | 119.1 |
C1—O1—C7 | 107.4 (2) | C6—C5—C4 | 121.8 (3) |
C1—N1—HN1 | 123 (3) | C6—C5—H5 | 119.1 |
C1—N1—C2 | 109.7 (3) | C5—C6—H6 | 122.4 |
C2—N1—HN1 | 128 (3) | C7—C6—C5 | 115.2 (3) |
O1—C1—S1 | 122.1 (2) | C7—C6—H6 | 122.4 |
N1—C1—S1 | 128.6 (3) | C2—C7—O1 | 108.5 (3) |
N1—C1—O1 | 109.2 (3) | C6—C7—O1 | 128.1 (3) |
C3—C2—N1 | 133.4 (3) | C6—C7—C2 | 123.5 (3) |
I1—C8—C9—F1 | 1.5 (4) | C1—N1—C2—C7 | −0.1 (4) |
I1—C8—C9—C10i | −178.3 (3) | C2—N1—C1—S1 | −179.1 (3) |
I1—C8—C10—F2 | −2.3 (4) | C2—N1—C1—O1 | −0.4 (4) |
I1—C8—C10—C9i | 178.3 (3) | C2—C3—C4—C5 | 0.4 (5) |
C9—C8—C10—F2 | 178.5 (3) | C3—C2—C7—O1 | −178.4 (3) |
C9—C8—C10—C9i | −0.9 (6) | C3—C2—C7—C6 | 1.1 (5) |
C10—C8—C9—F1 | −179.4 (3) | C3—C4—C5—C6 | 0.3 (6) |
C10—C8—C9—C10i | 0.9 (6) | C4—C5—C6—C7 | −0.3 (5) |
N1—C2—C3—C4 | −179.6 (3) | C5—C6—C7—O1 | 179.0 (3) |
N1—C2—C7—O1 | 0.5 (3) | C5—C6—C7—C2 | −0.4 (5) |
N1—C2—C7—C6 | 180.0 (3) | C7—O1—C1—S1 | 179.5 (2) |
C1—O1—C7—C2 | −0.8 (3) | C7—O1—C1—N1 | 0.8 (3) |
C1—O1—C7—C6 | 179.8 (3) | C7—C2—C3—C4 | −1.0 (5) |
C1—N1—C2—C3 | 178.6 (4) |
Symmetry code: (i) −x+3/2, −y+3/2, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—HN1···S1ii | 0.87 (4) | 2.45 (4) | 3.316 (3) | 178 (4) |
C3—H3···I1iii | 0.95 | 3.16 | 4.066 (3) | 159 |
Symmetry codes: (ii) −x+1, −y, −z+1; (iii) −x+1, −y+1, −z+1. |
C6F3I3·C7H5NOS | F(000) = 1200 |
Mr = 660.94 | Dx = 2.715 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 14.9295 (7) Å | Cell parameters from 9982 reflections |
b = 4.6119 (2) Å | θ = 2.7–26.5° |
c = 23.5065 (12) Å | µ = 5.96 mm−1 |
β = 92.548 (2)° | T = 100 K |
V = 1616.90 (13) Å3 | Column, colourless |
Z = 4 | 0.22 × 0.06 × 0.05 mm |
Bruker D8 Venture Photon 2 diffractometer | 2845 reflections with I > 2σ(I) |
Radiation source: Incoatec IµS | Rint = 0.050 |
φ and ω scans | θmax = 26.6°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2017) | h = −18→18 |
Tmin = 0.551, Tmax = 0.745 | k = −5→5 |
19413 measured reflections | l = −29→29 |
3348 independent reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.029 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.061 | w = 1/[σ2(Fo2) + (0.0015P)2 + 8.0148P] where P = (Fo2 + 2Fc2)/3 |
S = 1.22 | (Δ/σ)max = 0.002 |
3348 reflections | Δρmax = 0.80 e Å−3 |
203 parameters | Δρmin = −0.77 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 | 0.70807 (2) | 0.45232 (7) | 0.55419 (2) | 0.01748 (9) | |
I2 | 0.67869 (2) | 1.23515 (8) | 0.76030 (2) | 0.02173 (10) | |
I3 | 0.36351 (2) | 1.08539 (8) | 0.59175 (2) | 0.02080 (10) | |
F1 | 0.75694 (18) | 0.8001 (7) | 0.66897 (14) | 0.0224 (7) | |
F2 | 0.4884 (2) | 1.2983 (7) | 0.69902 (14) | 0.0233 (7) | |
F3 | 0.50893 (19) | 0.6840 (7) | 0.54104 (13) | 0.0216 (7) | |
C8 | 0.6336 (3) | 0.7273 (11) | 0.6051 (2) | 0.0148 (10) | |
C9 | 0.6700 (3) | 0.8566 (12) | 0.6536 (2) | 0.0171 (11) | |
C10 | 0.6230 (3) | 1.0473 (12) | 0.6861 (2) | 0.0172 (11) | |
C11 | 0.5357 (3) | 1.1100 (11) | 0.6684 (2) | 0.0182 (11) | |
C12 | 0.4950 (3) | 0.9888 (12) | 0.6197 (2) | 0.0161 (11) | |
C13 | 0.5456 (3) | 0.8001 (11) | 0.5888 (2) | 0.0150 (11) | |
S1 | 0.85264 (8) | 0.0073 (3) | 0.48739 (6) | 0.0189 (3) | |
O1 | 0.8417 (2) | 0.3886 (8) | 0.40283 (15) | 0.0173 (8) | |
N1 | 0.9806 (3) | 0.3173 (10) | 0.43450 (19) | 0.0160 (9) | |
HN1 | 1.021 (4) | 0.235 (15) | 0.456 (3) | 0.04 (2)* | |
C1 | 0.8953 (3) | 0.2405 (12) | 0.4417 (2) | 0.0179 (11) | |
C2 | 0.9850 (3) | 0.5192 (11) | 0.3901 (2) | 0.0161 (11) | |
C3 | 1.0549 (4) | 0.6679 (12) | 0.3661 (2) | 0.0214 (12) | |
H3 | 1.115554 | 0.640591 | 0.378875 | 0.026* | |
C4 | 1.0309 (4) | 0.8596 (12) | 0.3222 (2) | 0.0209 (12) | |
H4 | 1.076369 | 0.965301 | 0.304220 | 0.025* | |
C5 | 0.9402 (4) | 0.9002 (12) | 0.3038 (2) | 0.0215 (12) | |
H5 | 0.926165 | 1.034052 | 0.274018 | 0.026* | |
C6 | 0.8718 (3) | 0.7504 (12) | 0.3281 (2) | 0.0194 (11) | |
H6 | 0.810884 | 0.774932 | 0.315558 | 0.023* | |
C7 | 0.8969 (3) | 0.5632 (11) | 0.3715 (2) | 0.0175 (11) |
U11 | U22 | U33 | U12 | U13 | U23 | |
I1 | 0.01571 (16) | 0.01825 (18) | 0.01870 (18) | 0.00147 (13) | 0.00332 (13) | 0.00178 (14) |
I2 | 0.02249 (18) | 0.0226 (2) | 0.01963 (19) | −0.00506 (14) | −0.00417 (14) | −0.00151 (15) |
I3 | 0.01328 (16) | 0.0296 (2) | 0.01939 (19) | 0.00433 (14) | −0.00095 (13) | 0.00351 (16) |
F1 | 0.0106 (14) | 0.0263 (18) | 0.0298 (18) | 0.0009 (12) | −0.0040 (13) | 0.0000 (15) |
F2 | 0.0196 (15) | 0.0230 (18) | 0.0274 (18) | 0.0043 (13) | 0.0018 (13) | −0.0061 (15) |
F3 | 0.0164 (15) | 0.0279 (18) | 0.0201 (16) | 0.0002 (13) | −0.0031 (12) | −0.0072 (14) |
C8 | 0.019 (3) | 0.006 (2) | 0.018 (3) | 0.0031 (19) | −0.004 (2) | −0.002 (2) |
C9 | 0.010 (2) | 0.021 (3) | 0.020 (3) | −0.001 (2) | 0.001 (2) | 0.007 (2) |
C10 | 0.015 (2) | 0.024 (3) | 0.012 (3) | −0.003 (2) | 0.000 (2) | 0.001 (2) |
C11 | 0.018 (3) | 0.011 (3) | 0.026 (3) | 0.001 (2) | 0.007 (2) | 0.003 (2) |
C12 | 0.011 (2) | 0.020 (3) | 0.017 (3) | −0.001 (2) | −0.001 (2) | 0.002 (2) |
C13 | 0.015 (2) | 0.015 (3) | 0.014 (3) | −0.0009 (19) | −0.002 (2) | 0.001 (2) |
S1 | 0.0167 (6) | 0.0202 (7) | 0.0200 (7) | 0.0025 (5) | 0.0036 (5) | 0.0035 (6) |
O1 | 0.0153 (17) | 0.019 (2) | 0.0177 (19) | 0.0016 (14) | 0.0007 (14) | 0.0059 (16) |
N1 | 0.012 (2) | 0.023 (3) | 0.012 (2) | 0.0051 (18) | −0.0012 (17) | 0.0016 (19) |
C1 | 0.016 (2) | 0.022 (3) | 0.016 (3) | 0.006 (2) | −0.002 (2) | −0.005 (2) |
C2 | 0.014 (2) | 0.015 (3) | 0.018 (3) | 0.004 (2) | −0.001 (2) | −0.004 (2) |
C3 | 0.018 (3) | 0.025 (3) | 0.021 (3) | 0.002 (2) | 0.002 (2) | −0.001 (2) |
C4 | 0.023 (3) | 0.020 (3) | 0.020 (3) | −0.002 (2) | 0.011 (2) | −0.002 (2) |
C5 | 0.037 (3) | 0.017 (3) | 0.011 (3) | 0.004 (2) | 0.003 (2) | 0.002 (2) |
C6 | 0.016 (3) | 0.021 (3) | 0.021 (3) | 0.005 (2) | −0.002 (2) | −0.002 (2) |
C7 | 0.018 (3) | 0.014 (3) | 0.020 (3) | −0.001 (2) | 0.002 (2) | −0.004 (2) |
I1—C8 | 2.096 (5) | O1—C7 | 1.387 (6) |
I2—C10 | 2.086 (5) | N1—HN1 | 0.85 (7) |
I3—C12 | 2.091 (5) | N1—C1 | 1.340 (7) |
F1—C9 | 1.356 (5) | N1—C2 | 1.403 (7) |
F2—C11 | 1.347 (6) | C2—C3 | 1.389 (8) |
F3—C13 | 1.340 (6) | C2—C7 | 1.383 (7) |
C8—C9 | 1.378 (7) | C3—H3 | 0.9500 |
C8—C13 | 1.392 (7) | C3—C4 | 1.393 (8) |
C9—C10 | 1.378 (8) | C4—H4 | 0.9500 |
C10—C11 | 1.381 (7) | C4—C5 | 1.415 (8) |
C11—C12 | 1.389 (7) | C5—H5 | 0.9500 |
C12—C13 | 1.379 (7) | C5—C6 | 1.377 (8) |
S1—C1 | 1.666 (6) | C6—H6 | 0.9500 |
O1—C1 | 1.370 (6) | C6—C7 | 1.376 (8) |
C9—C8—I1 | 122.3 (4) | O1—C1—S1 | 121.6 (4) |
C9—C8—C13 | 117.1 (5) | N1—C1—S1 | 130.2 (4) |
C13—C8—I1 | 120.5 (4) | N1—C1—O1 | 108.3 (5) |
F1—C9—C8 | 118.4 (5) | C3—C2—N1 | 133.7 (5) |
F1—C9—C10 | 118.7 (5) | C7—C2—N1 | 104.9 (4) |
C10—C9—C8 | 122.9 (5) | C7—C2—C3 | 121.4 (5) |
C9—C10—I2 | 122.3 (4) | C2—C3—H3 | 121.9 |
C9—C10—C11 | 117.7 (5) | C2—C3—C4 | 116.2 (5) |
C11—C10—I2 | 120.0 (4) | C4—C3—H3 | 121.9 |
F2—C11—C10 | 119.0 (5) | C3—C4—H4 | 119.3 |
F2—C11—C12 | 118.7 (5) | C3—C4—C5 | 121.4 (5) |
C10—C11—C12 | 122.4 (5) | C5—C4—H4 | 119.3 |
C11—C12—I3 | 122.9 (4) | C4—C5—H5 | 119.2 |
C13—C12—I3 | 119.8 (4) | C6—C5—C4 | 121.6 (5) |
C13—C12—C11 | 117.3 (5) | C6—C5—H5 | 119.2 |
F3—C13—C8 | 118.6 (4) | C5—C6—H6 | 122.0 |
F3—C13—C12 | 118.7 (4) | C7—C6—C5 | 116.1 (5) |
C12—C13—C8 | 122.7 (5) | C7—C6—H6 | 122.0 |
C1—O1—C7 | 107.6 (4) | C2—C7—O1 | 109.0 (5) |
C1—N1—HN1 | 117 (5) | C6—C7—O1 | 127.6 (5) |
C1—N1—C2 | 110.2 (4) | C6—C7—C2 | 123.4 (5) |
C2—N1—HN1 | 132 (5) | ||
I1—C8—C9—F1 | −0.7 (7) | C13—C8—C9—F1 | −177.0 (5) |
I1—C8—C9—C10 | 177.2 (4) | C13—C8—C9—C10 | 0.9 (8) |
I1—C8—C13—F3 | 2.0 (7) | N1—C2—C3—C4 | −178.6 (5) |
I1—C8—C13—C12 | −177.5 (4) | N1—C2—C7—O1 | −1.3 (6) |
I2—C10—C11—F2 | 1.5 (7) | N1—C2—C7—C6 | 179.5 (5) |
I2—C10—C11—C12 | −179.3 (4) | C1—O1—C7—C2 | 1.3 (6) |
I3—C12—C13—F3 | 0.4 (7) | C1—O1—C7—C6 | −179.6 (5) |
I3—C12—C13—C8 | 179.9 (4) | C1—N1—C2—C3 | 179.1 (6) |
F1—C9—C10—I2 | −3.2 (7) | C1—N1—C2—C7 | 0.9 (6) |
F1—C9—C10—C11 | 177.6 (5) | C2—N1—C1—S1 | 179.1 (4) |
F2—C11—C12—I3 | −0.1 (7) | C2—N1—C1—O1 | −0.2 (6) |
F2—C11—C12—C13 | 179.1 (5) | C2—C3—C4—C5 | 0.5 (8) |
C8—C9—C10—I2 | 178.9 (4) | C3—C2—C7—O1 | −179.7 (5) |
C8—C9—C10—C11 | −0.3 (8) | C3—C2—C7—C6 | 1.0 (8) |
C9—C8—C13—F3 | 178.3 (5) | C3—C4—C5—C6 | −0.6 (8) |
C9—C8—C13—C12 | −1.1 (8) | C4—C5—C6—C7 | 0.8 (8) |
C9—C10—C11—F2 | −179.2 (5) | C5—C6—C7—O1 | 179.9 (5) |
C9—C10—C11—C12 | −0.1 (8) | C5—C6—C7—C2 | −1.1 (8) |
C10—C11—C12—I3 | −179.2 (4) | C7—O1—C1—S1 | 180.0 (4) |
C10—C11—C12—C13 | −0.1 (8) | C7—O1—C1—N1 | −0.7 (6) |
C11—C12—C13—F3 | −178.7 (5) | C7—C2—C3—C4 | −0.7 (8) |
C11—C12—C13—C8 | 0.7 (8) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—HN1···S1i | 0.85 (7) | 2.53 (7) | 3.377 (4) | 176 (6) |
C3—H3···I1ii | 0.95 | 3.04 | 3.969 (5) | 167 |
C6—H6···I2iii | 0.95 | 3.23 | 4.009 (5) | 140 |
Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x+2, −y+1, −z+1; (iii) x, −y+5/2, z−1/2. |
4C6F4I2·3C7H5NS2 | V = 2830.9 (5) Å3 |
Mr = 2109.16 | Z = 2 |
Triclinic, P1 | F(000) = 1940 |
a = 7.9410 (8) Å | Dx = 2.474 Mg m−3 |
b = 14.8483 (15) Å | Mo Kα radiation, λ = 0.71073 Å |
c = 24.641 (3) Å | µ = 4.69 mm−1 |
α = 79.264 (4)° | T = 100 K |
β = 87.104 (4)° | Plate, colourless |
γ = 82.784 (4)° | 0.30 × 0.13 × 0.04 mm |
Bruker D8 Venture Photon 2 diffractometer | 11325 reflections with I > 2σ(I) |
Radiation source: Incoatec IµS | Rint = 0.067 |
φ and ω scans | θmax = 27.2°, θmin = 2.5° |
Absorption correction: multi-scan (SADABS; Bruker, 2017) | h = −10→10 |
Tmin = 0.570, Tmax = 0.746 | k = −19→19 |
78566 measured reflections | l = −31→31 |
12466 independent reflections |
Refinement on F2 | 66 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.067 | H-atom parameters constrained |
wR(F2) = 0.220 | w = 1/[σ2(Fo2) + (0.1285P)2 + 109.2112P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
12466 reflections | Δρmax = 2.61 e Å−3 |
704 parameters | Δρmin = −1.48 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 | 0.36226 (13) | 1.16753 (7) | 0.05962 (4) | 0.0199 (2) | |
I2 | −0.11193 (13) | 1.17703 (7) | 0.07045 (4) | 0.0192 (2) | |
S3 | 0.8569 (5) | 0.2851 (3) | 0.27854 (18) | 0.0222 (8) | |
S4 | 0.9358 (5) | 0.3501 (3) | 0.15807 (18) | 0.0219 (8) | |
F1 | −0.1901 (12) | 0.9764 (7) | 0.0748 (4) | 0.023 (2) | |
F2 | 0.0046 (12) | 0.8143 (6) | 0.0705 (4) | 0.0210 (18) | |
F3 | 0.3454 (12) | 0.8083 (6) | 0.0614 (4) | 0.0218 (19) | |
F4 | 0.4959 (11) | 0.9599 (7) | 0.0585 (4) | 0.023 (2) | |
N2 | 0.7575 (18) | 0.4523 (10) | 0.2157 (6) | 0.022 (3) | |
HN2 | 0.702118 | 0.472763 | 0.243675 | 0.026* | |
C8 | 0.8414 (19) | 0.3657 (12) | 0.2214 (7) | 0.022 (3) | |
C9 | 0.8613 (18) | 0.4590 (11) | 0.1256 (8) | 0.022 (3) | |
C10 | 0.877 (2) | 0.5034 (12) | 0.0712 (7) | 0.025 (3) | |
H10 | 0.946102 | 0.474610 | 0.045108 | 0.030* | |
C11 | 0.792 (3) | 0.5893 (13) | 0.0558 (8) | 0.033 (3) | |
H11 | 0.792908 | 0.617175 | 0.017859 | 0.040* | |
C12 | 0.704 (2) | 0.6375 (13) | 0.0933 (8) | 0.029 (3) | |
H12 | 0.656903 | 0.699744 | 0.081256 | 0.035* | |
C13 | 0.683 (2) | 0.5975 (11) | 0.1470 (8) | 0.024 (3) | |
H13 | 0.616999 | 0.629053 | 0.172475 | 0.029* | |
C14 | 0.764 (2) | 0.5071 (12) | 0.1632 (7) | 0.021 (3) | |
C22 | 0.2314 (19) | 1.0522 (10) | 0.0647 (6) | 0.014 (3) | |
C23 | 0.0557 (18) | 1.0544 (10) | 0.0689 (6) | 0.016 (3) | |
C24 | −0.0213 (17) | 0.9775 (10) | 0.0714 (6) | 0.014 (2) | |
C25 | 0.0758 (19) | 0.8923 (10) | 0.0684 (6) | 0.015 (2) | |
C26 | 0.2483 (19) | 0.8892 (10) | 0.0642 (6) | 0.016 (3) | |
C27 | 0.3254 (18) | 0.9675 (10) | 0.0619 (6) | 0.015 (3) | |
I3 | 0.64678 (12) | 1.13261 (7) | 0.23166 (4) | 0.0194 (2) | |
I4 | 0.18439 (13) | 1.10869 (8) | 0.23135 (5) | 0.0227 (2) | |
F5 | 0.1660 (12) | 0.9119 (8) | 0.2046 (5) | 0.028 (2) | |
F6 | 0.4004 (14) | 0.7773 (7) | 0.1803 (5) | 0.032 (2) | |
F7 | 0.7341 (13) | 0.8013 (7) | 0.1742 (5) | 0.028 (2) | |
F8 | 0.8342 (12) | 0.9554 (7) | 0.1967 (5) | 0.027 (2) | |
C28 | 0.548 (2) | 1.0190 (11) | 0.2120 (6) | 0.019 (3) | |
C29 | 0.3765 (17) | 1.0068 (10) | 0.2139 (6) | 0.014 (3) | |
C30 | 0.3304 (19) | 0.9261 (12) | 0.2037 (6) | 0.019 (3) | |
C31 | 0.447 (2) | 0.8555 (11) | 0.1910 (7) | 0.020 (3) | |
C32 | 0.618 (2) | 0.8672 (12) | 0.1869 (7) | 0.022 (3) | |
C33 | 0.6663 (18) | 0.9461 (11) | 0.1986 (7) | 0.018 (3) | |
I5 | 0.23233 (12) | 0.71859 (7) | 0.32850 (4) | 0.0183 (2) | |
I6 | −0.23322 (12) | 0.70593 (7) | 0.32425 (4) | 0.0200 (2) | |
F9 | −0.4093 (13) | 0.8951 (8) | 0.3451 (4) | 0.028 (2) | |
F10 | −0.2991 (13) | 1.0414 (7) | 0.3748 (5) | 0.028 (2) | |
F11 | 0.0385 (13) | 1.0534 (7) | 0.3782 (5) | 0.027 (2) | |
F12 | 0.2640 (12) | 0.9152 (7) | 0.3547 (5) | 0.026 (2) | |
C34 | 0.0485 (19) | 0.8268 (10) | 0.3394 (6) | 0.017 (3) | |
C35 | −0.1293 (18) | 0.8223 (10) | 0.3377 (6) | 0.015 (2) | |
C36 | −0.2433 (18) | 0.8975 (10) | 0.3469 (6) | 0.016 (2) | |
C37 | −0.1897 (18) | 0.9730 (10) | 0.3622 (6) | 0.015 (2) | |
C38 | −0.016 (2) | 0.9776 (11) | 0.3644 (7) | 0.020 (3) | |
C39 | 0.097 (2) | 0.9065 (10) | 0.3535 (7) | 0.019 (3) | |
I7 | 0.02233 (13) | 0.46575 (7) | 0.37019 (4) | 0.0196 (2) | |
I8 | −0.02757 (15) | 0.35978 (8) | 0.51719 (5) | 0.0269 (3) | |
F13 | 0.1440 (16) | 0.1570 (8) | 0.5289 (4) | 0.036 (3) | |
F14 | 0.3307 (17) | 0.0627 (7) | 0.4593 (5) | 0.037 (3) | |
F15 | 0.3867 (14) | 0.1426 (7) | 0.3536 (4) | 0.030 (2) | |
F16 | 0.2600 (13) | 0.3180 (7) | 0.3159 (4) | 0.026 (2) | |
C40 | 0.1256 (19) | 0.3310 (9) | 0.4037 (6) | 0.015 (3) | |
C41 | 0.100 (2) | 0.2902 (12) | 0.4582 (7) | 0.020 (3) | |
C42 | 0.171 (2) | 0.2029 (13) | 0.4767 (7) | 0.025 (3) | |
C43 | 0.263 (2) | 0.1486 (12) | 0.4419 (7) | 0.023 (3) | |
C44 | 0.292 (2) | 0.1890 (11) | 0.3876 (7) | 0.022 (3) | |
C45 | 0.223 (2) | 0.2791 (10) | 0.3680 (6) | 0.017 (3) | |
S1 | 0.5243 (5) | 0.5375 (3) | 0.31454 (16) | 0.0193 (7) | |
S2 | 0.4491 (5) | 0.4693 (3) | 0.43557 (17) | 0.0217 (8) | |
N1 | 0.6185 (17) | 0.3686 (9) | 0.3737 (6) | 0.020 (2) | |
HN1 | 0.671175 | 0.349037 | 0.345043 | 0.025* | |
C1 | 0.5386 (19) | 0.4543 (10) | 0.3712 (6) | 0.0156 (18) | |
C2 | 0.518 (2) | 0.3547 (12) | 0.4654 (7) | 0.022 (3) | |
C3 | 0.498 (2) | 0.3107 (13) | 0.5198 (6) | 0.024 (3) | |
H3 | 0.442344 | 0.342280 | 0.547045 | 0.029* | |
C4 | 0.566 (3) | 0.2171 (16) | 0.5328 (9) | 0.042 (5) | |
H4 | 0.548501 | 0.183201 | 0.568902 | 0.050* | |
C5 | 0.659 (3) | 0.1730 (14) | 0.4927 (8) | 0.037 (5) | |
H5 | 0.705227 | 0.110313 | 0.502792 | 0.044* | |
C6 | 0.684 (2) | 0.2196 (12) | 0.4377 (8) | 0.028 (4) | |
H6 | 0.746640 | 0.190247 | 0.410614 | 0.033* | |
C7 | 0.610 (2) | 0.3135 (11) | 0.4259 (8) | 0.024 (3) | |
S5 | 0.5779 (5) | 0.3528 (3) | 0.04223 (16) | 0.0185 (7) | |
S6 | 0.4242 (5) | 0.3654 (3) | 0.15534 (16) | 0.0196 (7) | |
N3 | 0.3879 (16) | 0.4977 (9) | 0.0733 (5) | 0.016 (2) | |
HN3 | 0.397601 | 0.531273 | 0.040138 | 0.019* | |
C15 | 0.4623 (19) | 0.4112 (10) | 0.0858 (6) | 0.016 (3) | |
C16 | 0.3061 (19) | 0.4678 (10) | 0.1659 (6) | 0.016 (3) | |
C17 | 0.216 (2) | 0.4894 (11) | 0.2134 (6) | 0.021 (3) | |
H17 | 0.215714 | 0.445412 | 0.246790 | 0.025* | |
C18 | 0.128 (2) | 0.5768 (12) | 0.2101 (7) | 0.025 (3) | |
H18 | 0.074519 | 0.594232 | 0.242502 | 0.030* | |
C19 | 0.116 (2) | 0.6408 (11) | 0.1597 (8) | 0.026 (4) | |
H19 | 0.048383 | 0.698679 | 0.158241 | 0.032* | |
C20 | 0.2008 (19) | 0.6197 (10) | 0.1133 (7) | 0.019 (3) | |
H20 | 0.197834 | 0.663313 | 0.079745 | 0.022* | |
C21 | 0.2922 (19) | 0.5323 (10) | 0.1166 (6) | 0.015 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
I1 | 0.0179 (5) | 0.0178 (5) | 0.0249 (5) | −0.0061 (4) | 0.0017 (4) | −0.0046 (4) |
I2 | 0.0168 (5) | 0.0176 (4) | 0.0238 (5) | 0.0017 (3) | 0.0003 (4) | −0.0076 (4) |
S3 | 0.026 (2) | 0.0144 (17) | 0.026 (2) | 0.0011 (14) | 0.0023 (16) | −0.0064 (15) |
S4 | 0.0223 (19) | 0.0171 (18) | 0.027 (2) | −0.0012 (14) | 0.0041 (16) | −0.0092 (15) |
F1 | 0.014 (4) | 0.025 (5) | 0.030 (5) | −0.001 (4) | 0.001 (4) | −0.004 (4) |
F2 | 0.021 (2) | 0.022 (2) | 0.022 (2) | −0.0089 (18) | −0.0027 (18) | −0.0044 (18) |
F3 | 0.016 (4) | 0.016 (4) | 0.032 (5) | 0.004 (3) | 0.000 (4) | −0.006 (4) |
F4 | 0.007 (4) | 0.024 (5) | 0.038 (6) | −0.004 (3) | 0.001 (4) | −0.006 (4) |
N2 | 0.020 (7) | 0.020 (7) | 0.026 (7) | 0.002 (5) | 0.001 (5) | −0.009 (6) |
C8 | 0.011 (7) | 0.025 (8) | 0.032 (9) | −0.002 (6) | −0.011 (6) | −0.011 (7) |
C9 | 0.004 (6) | 0.021 (8) | 0.043 (10) | 0.000 (5) | −0.001 (6) | −0.011 (7) |
C10 | 0.030 (7) | 0.021 (7) | 0.025 (7) | 0.001 (6) | −0.012 (6) | −0.009 (6) |
C11 | 0.042 (7) | 0.028 (7) | 0.031 (7) | 0.011 (6) | −0.019 (6) | −0.013 (6) |
C12 | 0.028 (7) | 0.025 (7) | 0.034 (7) | 0.002 (6) | −0.010 (6) | −0.008 (6) |
C13 | 0.012 (7) | 0.019 (8) | 0.041 (10) | −0.001 (6) | −0.005 (7) | −0.007 (7) |
C14 | 0.023 (8) | 0.024 (8) | 0.019 (7) | −0.009 (6) | 0.015 (6) | −0.010 (6) |
C22 | 0.018 (7) | 0.014 (6) | 0.006 (6) | 0.004 (5) | 0.001 (5) | 0.001 (5) |
C23 | 0.009 (5) | 0.018 (6) | 0.018 (6) | 0.001 (5) | 0.002 (5) | −0.001 (5) |
C24 | 0.005 (5) | 0.016 (5) | 0.021 (5) | 0.002 (4) | 0.004 (4) | −0.004 (4) |
C25 | 0.016 (6) | 0.013 (6) | 0.016 (6) | 0.000 (5) | 0.002 (5) | −0.004 (5) |
C26 | 0.016 (7) | 0.015 (7) | 0.017 (7) | 0.006 (5) | −0.008 (6) | −0.008 (6) |
C27 | 0.012 (6) | 0.012 (6) | 0.020 (7) | 0.001 (5) | 0.004 (5) | −0.005 (6) |
I3 | 0.0164 (5) | 0.0180 (5) | 0.0230 (5) | −0.0020 (3) | 0.0015 (4) | −0.0025 (4) |
I4 | 0.0135 (4) | 0.0257 (5) | 0.0256 (5) | 0.0039 (4) | 0.0016 (4) | −0.0007 (4) |
F5 | 0.010 (4) | 0.041 (6) | 0.036 (6) | −0.007 (4) | 0.001 (4) | −0.012 (5) |
F6 | 0.026 (5) | 0.025 (5) | 0.049 (7) | −0.004 (4) | −0.003 (5) | −0.013 (5) |
F7 | 0.022 (5) | 0.028 (5) | 0.036 (6) | 0.000 (4) | 0.004 (4) | −0.015 (4) |
F8 | 0.009 (4) | 0.028 (5) | 0.047 (6) | −0.003 (4) | 0.001 (4) | −0.013 (5) |
C28 | 0.019 (8) | 0.017 (7) | 0.016 (7) | 0.001 (6) | 0.008 (6) | 0.001 (6) |
C29 | 0.006 (6) | 0.018 (7) | 0.022 (7) | −0.003 (5) | −0.001 (5) | −0.010 (6) |
C30 | 0.013 (7) | 0.034 (9) | 0.008 (6) | −0.003 (6) | −0.005 (5) | −0.001 (6) |
C31 | 0.016 (7) | 0.020 (7) | 0.025 (8) | 0.000 (6) | −0.005 (6) | −0.004 (6) |
C32 | 0.020 (8) | 0.027 (8) | 0.021 (8) | −0.001 (6) | −0.004 (6) | −0.007 (6) |
C33 | 0.004 (6) | 0.022 (8) | 0.028 (8) | −0.002 (5) | 0.003 (6) | −0.007 (6) |
I5 | 0.0127 (4) | 0.0181 (4) | 0.0233 (5) | 0.0019 (3) | 0.0022 (4) | −0.0047 (4) |
I6 | 0.0161 (5) | 0.0194 (5) | 0.0249 (5) | −0.0025 (4) | −0.0033 (4) | −0.0039 (4) |
F9 | 0.016 (5) | 0.031 (5) | 0.032 (5) | 0.002 (4) | −0.001 (4) | 0.004 (4) |
F10 | 0.022 (5) | 0.020 (5) | 0.042 (6) | 0.008 (4) | 0.002 (4) | −0.010 (4) |
F11 | 0.025 (5) | 0.022 (5) | 0.038 (6) | −0.004 (4) | −0.001 (4) | −0.013 (4) |
F12 | 0.012 (4) | 0.020 (5) | 0.043 (6) | −0.002 (4) | −0.001 (4) | 0.003 (4) |
C34 | 0.014 (7) | 0.008 (6) | 0.023 (7) | 0.003 (5) | 0.003 (6) | 0.007 (5) |
C35 | 0.008 (5) | 0.016 (5) | 0.020 (5) | −0.001 (4) | −0.003 (4) | 0.004 (4) |
C36 | 0.006 (4) | 0.017 (5) | 0.020 (5) | 0.001 (4) | −0.001 (4) | 0.004 (4) |
C37 | 0.006 (5) | 0.017 (5) | 0.021 (5) | 0.001 (4) | 0.001 (4) | 0.001 (4) |
C38 | 0.021 (8) | 0.017 (7) | 0.021 (7) | −0.001 (6) | −0.004 (6) | 0.003 (6) |
C39 | 0.027 (8) | 0.010 (6) | 0.019 (7) | −0.004 (6) | 0.001 (6) | 0.000 (5) |
I7 | 0.0181 (5) | 0.0162 (4) | 0.0234 (5) | 0.0003 (3) | −0.0028 (4) | −0.0016 (4) |
I8 | 0.0288 (6) | 0.0313 (6) | 0.0212 (5) | −0.0007 (4) | 0.0039 (4) | −0.0091 (4) |
F13 | 0.048 (7) | 0.029 (6) | 0.022 (5) | −0.004 (5) | 0.001 (5) | 0.012 (4) |
F14 | 0.056 (8) | 0.018 (5) | 0.033 (6) | 0.009 (5) | −0.011 (5) | 0.000 (4) |
F15 | 0.031 (6) | 0.030 (5) | 0.030 (5) | 0.010 (4) | 0.007 (4) | −0.016 (4) |
F16 | 0.026 (5) | 0.030 (5) | 0.018 (5) | 0.003 (4) | 0.006 (4) | 0.001 (4) |
C40 | 0.019 (7) | 0.007 (6) | 0.017 (7) | 0.003 (5) | 0.002 (5) | −0.002 (5) |
C41 | 0.015 (6) | 0.027 (7) | 0.017 (6) | −0.002 (5) | −0.006 (5) | 0.003 (5) |
C42 | 0.019 (6) | 0.035 (7) | 0.013 (5) | 0.009 (5) | 0.001 (5) | 0.007 (5) |
C43 | 0.022 (6) | 0.022 (7) | 0.020 (6) | 0.004 (6) | −0.008 (5) | 0.004 (5) |
C44 | 0.024 (8) | 0.020 (8) | 0.024 (8) | −0.002 (6) | 0.002 (6) | −0.009 (6) |
C45 | 0.018 (7) | 0.014 (7) | 0.016 (7) | 0.003 (5) | 0.002 (6) | 0.000 (6) |
S1 | 0.0186 (17) | 0.0161 (17) | 0.0224 (18) | 0.0004 (14) | 0.0010 (14) | −0.0038 (14) |
S2 | 0.0197 (18) | 0.0264 (19) | 0.0195 (17) | 0.0001 (15) | 0.0006 (14) | −0.0077 (15) |
N1 | 0.020 (5) | 0.021 (5) | 0.023 (5) | −0.004 (4) | −0.001 (4) | −0.007 (4) |
C1 | 0.015 (4) | 0.019 (4) | 0.017 (4) | −0.006 (3) | −0.002 (3) | −0.010 (3) |
C2 | 0.015 (7) | 0.030 (9) | 0.021 (8) | −0.008 (6) | 0.003 (6) | −0.003 (7) |
C3 | 0.019 (8) | 0.042 (10) | 0.010 (7) | −0.005 (7) | 0.001 (6) | −0.001 (7) |
C4 | 0.041 (12) | 0.051 (13) | 0.032 (10) | −0.030 (10) | −0.007 (9) | 0.011 (9) |
C5 | 0.058 (13) | 0.026 (9) | 0.022 (9) | −0.008 (9) | −0.008 (8) | 0.010 (7) |
C6 | 0.031 (9) | 0.018 (8) | 0.033 (9) | −0.004 (7) | −0.012 (7) | 0.001 (7) |
C7 | 0.026 (8) | 0.014 (7) | 0.031 (9) | −0.002 (6) | −0.009 (7) | 0.002 (6) |
S5 | 0.0195 (18) | 0.0119 (16) | 0.0226 (18) | 0.0032 (13) | 0.0020 (14) | −0.0028 (14) |
S6 | 0.0213 (18) | 0.0154 (17) | 0.0201 (18) | 0.0013 (14) | −0.0005 (14) | −0.0005 (14) |
N3 | 0.016 (6) | 0.014 (6) | 0.017 (6) | 0.004 (5) | 0.000 (5) | −0.003 (5) |
C15 | 0.018 (7) | 0.011 (6) | 0.020 (7) | −0.002 (5) | −0.007 (6) | −0.001 (5) |
C16 | 0.013 (7) | 0.015 (7) | 0.019 (7) | −0.001 (5) | 0.002 (5) | −0.002 (6) |
C17 | 0.031 (9) | 0.021 (8) | 0.009 (6) | 0.001 (7) | −0.003 (6) | 0.002 (6) |
C18 | 0.016 (7) | 0.030 (9) | 0.028 (8) | 0.004 (6) | 0.001 (6) | −0.009 (7) |
C19 | 0.033 (9) | 0.012 (7) | 0.033 (9) | 0.007 (6) | −0.006 (7) | −0.008 (7) |
C20 | 0.016 (7) | 0.014 (7) | 0.024 (8) | −0.005 (6) | 0.013 (6) | 0.000 (6) |
C21 | 0.018 (7) | 0.012 (6) | 0.016 (7) | −0.005 (5) | 0.004 (5) | −0.004 (5) |
I1—C22 | 2.094 (15) | C35—C36 | 1.39 (2) |
I2—C23 | 2.121 (15) | C36—C37 | 1.37 (2) |
S3—C8 | 1.669 (18) | C37—C38 | 1.40 (2) |
S4—C8 | 1.738 (18) | C38—C39 | 1.35 (2) |
S4—C9 | 1.711 (17) | I7—C40 | 2.097 (14) |
F1—C24 | 1.341 (16) | I8—C41 | 2.086 (17) |
F2—C25 | 1.344 (17) | F13—C42 | 1.358 (19) |
F3—C26 | 1.355 (16) | F14—C43 | 1.320 (19) |
F4—C27 | 1.344 (17) | F15—C44 | 1.328 (18) |
N2—HN2 | 0.8800 | F16—C45 | 1.341 (18) |
N2—C8 | 1.36 (2) | C40—C41 | 1.38 (2) |
N2—C14 | 1.40 (2) | C40—C45 | 1.41 (2) |
C9—C10 | 1.39 (3) | C41—C42 | 1.35 (2) |
C9—C14 | 1.42 (2) | C42—C43 | 1.40 (2) |
C10—H10 | 0.9500 | C43—C44 | 1.38 (2) |
C10—C11 | 1.36 (2) | C44—C45 | 1.39 (2) |
C11—H11 | 0.9500 | S1—C1 | 1.680 (16) |
C11—C12 | 1.38 (3) | S2—C1 | 1.747 (15) |
C12—H12 | 0.9500 | S2—C2 | 1.755 (19) |
C12—C13 | 1.36 (3) | N1—HN1 | 0.8800 |
C13—H13 | 0.9500 | N1—C1 | 1.34 (2) |
C13—C14 | 1.41 (2) | N1—C7 | 1.39 (2) |
C22—C23 | 1.39 (2) | C2—C3 | 1.39 (2) |
C22—C27 | 1.391 (19) | C2—C7 | 1.38 (2) |
C23—C24 | 1.35 (2) | C3—H3 | 0.9500 |
C24—C25 | 1.408 (19) | C3—C4 | 1.41 (3) |
C25—C26 | 1.36 (2) | C4—H4 | 0.9500 |
C26—C27 | 1.37 (2) | C4—C5 | 1.41 (3) |
I3—C28 | 2.089 (16) | C5—H5 | 0.9500 |
I4—C29 | 2.097 (14) | C5—C6 | 1.42 (3) |
F5—C30 | 1.347 (18) | C6—H6 | 0.9500 |
F6—C31 | 1.336 (19) | C6—C7 | 1.43 (2) |
F7—C32 | 1.330 (19) | S5—C15 | 1.671 (16) |
F8—C33 | 1.355 (17) | S6—C15 | 1.749 (16) |
C28—C29 | 1.40 (2) | S6—C16 | 1.740 (15) |
C28—C33 | 1.42 (2) | N3—HN3 | 0.8800 |
C29—C30 | 1.37 (2) | N3—C15 | 1.331 (19) |
C30—C31 | 1.38 (2) | N3—C21 | 1.416 (19) |
C31—C32 | 1.38 (2) | C16—C17 | 1.41 (2) |
C32—C33 | 1.36 (2) | C16—C21 | 1.40 (2) |
I5—C34 | 2.077 (14) | C17—H17 | 0.9500 |
I6—C35 | 2.092 (15) | C17—C18 | 1.38 (2) |
F9—C36 | 1.326 (17) | C18—H18 | 0.9500 |
F10—C37 | 1.323 (17) | C18—C19 | 1.41 (3) |
F11—C38 | 1.359 (19) | C19—H19 | 0.9500 |
F12—C39 | 1.348 (19) | C19—C20 | 1.36 (2) |
C34—C35 | 1.43 (2) | C20—H20 | 0.9500 |
C34—C39 | 1.40 (2) | C20—C21 | 1.40 (2) |
C9—S4—C8 | 93.5 (8) | C39—C38—F11 | 120.7 (15) |
C8—N2—HN2 | 121.8 | C39—C38—C37 | 120.0 (15) |
C8—N2—C14 | 116.5 (14) | F12—C39—C34 | 119.1 (14) |
C14—N2—HN2 | 121.8 | F12—C39—C38 | 117.8 (14) |
S3—C8—S4 | 123.8 (10) | C38—C39—C34 | 123.1 (16) |
N2—C8—S3 | 127.4 (14) | C41—C40—I7 | 123.4 (11) |
N2—C8—S4 | 108.8 (13) | C41—C40—C45 | 118.8 (14) |
C10—C9—S4 | 131.6 (13) | C45—C40—I7 | 117.7 (11) |
C10—C9—C14 | 118.2 (15) | C40—C41—I8 | 123.5 (12) |
C14—C9—S4 | 110.2 (14) | C42—C41—I8 | 116.4 (12) |
C9—C10—H10 | 120.7 | C42—C41—C40 | 119.9 (15) |
C11—C10—C9 | 118.6 (17) | F13—C42—C43 | 114.0 (15) |
C11—C10—H10 | 120.7 | C41—C42—F13 | 123.0 (15) |
C10—C11—H11 | 118.7 | C41—C42—C43 | 122.7 (15) |
C10—C11—C12 | 122.6 (19) | F14—C43—C42 | 123.2 (15) |
C12—C11—H11 | 118.7 | F14—C43—C44 | 118.8 (16) |
C11—C12—H12 | 119.4 | C44—C43—C42 | 117.9 (15) |
C13—C12—C11 | 121.1 (18) | F15—C44—C43 | 120.7 (15) |
C13—C12—H12 | 119.4 | F15—C44—C45 | 119.1 (15) |
C12—C13—H13 | 121.5 | C43—C44—C45 | 120.3 (15) |
C12—C13—C14 | 116.9 (16) | F16—C45—C40 | 120.7 (13) |
C14—C13—H13 | 121.5 | F16—C45—C44 | 118.9 (14) |
N2—C14—C9 | 111.1 (15) | C44—C45—C40 | 120.3 (14) |
N2—C14—C13 | 126.8 (15) | C1—S2—C2 | 92.1 (8) |
C13—C14—C9 | 122.1 (16) | C1—N1—HN1 | 123.1 |
C23—C22—I1 | 124.6 (10) | C1—N1—C7 | 113.8 (14) |
C23—C22—C27 | 117.2 (14) | C7—N1—HN1 | 123.1 |
C27—C22—I1 | 118.1 (11) | S1—C1—S2 | 123.6 (9) |
C22—C23—I2 | 123.4 (11) | N1—C1—S1 | 125.7 (12) |
C24—C23—I2 | 114.8 (10) | N1—C1—S2 | 110.7 (12) |
C24—C23—C22 | 121.8 (14) | C3—C2—S2 | 128.6 (14) |
F1—C24—C23 | 123.9 (13) | C7—C2—S2 | 108.1 (12) |
F1—C24—C25 | 115.8 (13) | C7—C2—C3 | 123.1 (17) |
C23—C24—C25 | 120.3 (13) | C2—C3—H3 | 121.6 |
F2—C25—C24 | 122.3 (13) | C2—C3—C4 | 116.9 (17) |
F2—C25—C26 | 119.2 (13) | C4—C3—H3 | 121.6 |
C26—C25—C24 | 118.5 (13) | C3—C4—H4 | 119.6 |
F3—C26—C25 | 120.0 (13) | C3—C4—C5 | 120.8 (17) |
F3—C26—C27 | 119.2 (13) | C5—C4—H4 | 119.6 |
C25—C26—C27 | 120.8 (13) | C4—C5—H5 | 119.0 |
F4—C27—C22 | 120.4 (13) | C4—C5—C6 | 122.0 (19) |
F4—C27—C26 | 118.2 (13) | C6—C5—H5 | 119.0 |
C26—C27—C22 | 121.4 (14) | C5—C6—H6 | 122.2 |
C29—C28—I3 | 125.4 (11) | C5—C6—C7 | 115.5 (18) |
C29—C28—C33 | 117.2 (14) | C7—C6—H6 | 122.2 |
C33—C28—I3 | 117.3 (11) | N1—C7—C6 | 123.2 (17) |
C28—C29—I4 | 122.4 (11) | C2—C7—N1 | 115.2 (15) |
C30—C29—I4 | 118.3 (10) | C2—C7—C6 | 121.5 (17) |
C30—C29—C28 | 119.3 (14) | C16—S6—C15 | 91.6 (7) |
F5—C30—C29 | 121.1 (14) | C15—N3—HN3 | 122.0 |
F5—C30—C31 | 116.1 (15) | C15—N3—C21 | 116.0 (13) |
C29—C30—C31 | 122.7 (14) | C21—N3—HN3 | 122.0 |
F6—C31—C30 | 122.3 (14) | S5—C15—S6 | 123.6 (9) |
F6—C31—C32 | 118.6 (15) | N3—C15—S5 | 125.8 (12) |
C30—C31—C32 | 119.1 (15) | N3—C15—S6 | 110.6 (12) |
F7—C32—C31 | 121.1 (15) | C17—C16—S6 | 129.9 (12) |
F7—C32—C33 | 119.9 (14) | C21—C16—S6 | 110.9 (11) |
C33—C32—C31 | 119.0 (15) | C21—C16—C17 | 118.9 (14) |
F8—C33—C28 | 118.8 (14) | C16—C17—H17 | 121.0 |
F8—C33—C32 | 118.6 (14) | C18—C17—C16 | 117.9 (15) |
C32—C33—C28 | 122.6 (14) | C18—C17—H17 | 121.0 |
C35—C34—I5 | 123.6 (11) | C17—C18—H18 | 119.0 |
C39—C34—I5 | 119.6 (11) | C17—C18—C19 | 121.9 (15) |
C39—C34—C35 | 116.6 (14) | C19—C18—H18 | 119.0 |
C34—C35—I6 | 123.6 (11) | C18—C19—H19 | 119.9 |
C36—C35—I6 | 116.8 (10) | C20—C19—C18 | 120.3 (15) |
C36—C35—C34 | 119.6 (14) | C20—C19—H19 | 119.9 |
F9—C36—C35 | 120.7 (14) | C19—C20—H20 | 121.0 |
F9—C36—C37 | 117.6 (13) | C19—C20—C21 | 118.0 (15) |
C37—C36—C35 | 121.5 (13) | C21—C20—H20 | 121.0 |
F10—C37—C36 | 121.4 (13) | C16—C21—N3 | 110.8 (13) |
F10—C37—C38 | 119.6 (14) | C20—C21—N3 | 126.5 (14) |
C36—C37—C38 | 119.0 (14) | C20—C21—C16 | 122.6 (14) |
F11—C38—C37 | 119.3 (14) | ||
I1—C22—C23—I2 | 0.4 (18) | F11—C38—C39—F12 | −3 (2) |
I1—C22—C23—C24 | 179.1 (11) | F11—C38—C39—C34 | 179.7 (14) |
I1—C22—C27—F4 | 2.9 (19) | C34—C35—C36—F9 | 179.6 (14) |
I1—C22—C27—C26 | −179.1 (11) | C34—C35—C36—C37 | −6 (2) |
I2—C23—C24—F1 | 0 (2) | C35—C34—C39—F12 | −178.7 (13) |
I2—C23—C24—C25 | 177.4 (11) | C35—C34—C39—C38 | −1 (2) |
S4—C9—C10—C11 | 174.9 (14) | C35—C36—C37—F10 | −175.0 (14) |
S4—C9—C14—N2 | 0.4 (17) | C35—C36—C37—C38 | 5 (2) |
S4—C9—C14—C13 | −178.2 (13) | C36—C37—C38—F11 | 178.3 (14) |
F1—C24—C25—F2 | −2 (2) | C36—C37—C38—C39 | − |