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

Watts, S.; Peloquin, A.J.; Bandara, M.; McMillen, C.D.; Pennington, W.T.

doi:10.1107/S2053229622009548

sigma-hole interactions

STRUCTURAL
CHEMISTRY

ISSN: 2053-2296

Volume 78| Part 12| December 2022| Pages 702-715

https://doi.org/10.1107/S2053229622009548

Open

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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

Spencer Watts,^a Andrew J. Peloquin,^a Madhushi Bandara,^a Colin D. McMillen ^a and William T. Pennington ^a ^*

^aDepartment of Chemistry, Clemson University, 219 Hunter Laboratories, Clemson, SC 29634, USA
^*Correspondence e-mail: billp@clemson.edu

Edited by T. Roseveare, University of Sheffield, United Kingdom (Received 21 August 2022; accepted 27 September 2022; online 9 November 2022)

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.

CCDC references: 2194060; 2194061; 2194062; 2194063; 2194064; 2194065; 2194066; 2194067; 2194068; 2194069; 2194070; 2194071; 2194072; 2194073; 2194074; 2194075; 2194076; 2194077

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.

Figure 1
Organoiodines and mercaptoimidazoles utilized in this study.

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 refinement details are summarized in Table 1. H atoms on C atoms were calculated in idealized positions riding on their parent atoms, with C—H = 0.98 Å and U_iso(H) = 1.5U_eq(C) for methyl H atoms, and C—H = 0.95 Å and U_iso(H) = 1.2U_eq(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.

Table 1
Experimental details

Experiments were carried out at 100 K with Mo Kα radiation using a Bruker D8 Venture Photon 2 diffractometer. Absorption was corrected for by multi-scan methods (SADABS; Bruker, 2017 ). H atoms were treated by a mixture of independent and constrained refinement, except for 3(MBZTH)·4(1,2-F₄DIB), for which H-atom parameters were constrained.

	2(IT)·(1,3-F₄DIB)	(IT)·(1,3,5-F₃I₃B)	4(MBZIM)·3(1,3-F₄DIB)	(MBZIM)·(1,4-F₄DIB)
Crystal data
Chemical formula	C₆F₄I₂·2C₃H₆N₂S	C₆F₃I₃·C₃H₆N₂S	3C₆F₄I₂·4C₇H₆N₂S	C₆F₄I₂·C₇H₆N₂S
M_r	606.18	611.92	1806.37	552.06
Crystal system, space group	Orthorhombic, Pbcn	Orthorhombic, Pbca	Triclinic, P $[\overline{1}]$	Monoclinic, P2₁/c
a, b, c (Å)	15.6704 (7), 8.9924 (4), 26.0573 (10)	18.0407 (14), 7.2816 (6), 22.1250 (19)	8.4573 (14), 17.725 (3), 18.759 (4)	5.5641 (2), 33.1320 (11), 8.4710 (3)
α, β, γ (°)	90, 90, 90	90, 90, 90	106.997 (7), 93.229 (7), 92.034 (7)	90, 92.754 (1), 90
V (Å³)	3671.9 (3)	2906.5 (4)	2680.9 (9)	1559.82 (9)
Z	8	8	2	4
μ (mm⁻¹)	3.69	6.61	3.72	4.20
Crystal size (mm)	0.18 × 0.17 × 0.13	0.22 × 0.08 × 0.04	0.34 × 0.04 × 0.04	0.22 × 0.18 × 0.06

Data collection
T_min, T_max	0.639, 0.746	0.563, 0.746	0.668, 0.746	0.501, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	112821, 5376, 5198	49179, 3615, 3220	118524, 12297, 10558	45583, 4579, 4211
R_int	0.035	0.043	0.056	0.050
(sin θ/λ)_max (Å⁻¹)	0.705	0.667	0.651	0.709

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.015, 0.032, 1.25	0.019, 0.040, 1.11	0.021, 0.041, 1.06	0.020, 0.044, 1.12
No. of reflections	5376	3615	12297	4579
No. of parameters	234	172	717	207
No. of restraints	0	2	8	0
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.37	0.57, −0.77	0.52, −0.75	0.49, −0.68

	(MBZIM)·(TIE)	(MMBZIM)·(1,2-F₄DIB)	2(MMBZIM)·(1,4-F₄DIB)·2(H₂O)	(MMBZIM)·(1,3,5-F₃I₃B)
Crystal data
Chemical formula	C₂I₄·C₇H₆N₂S	C₆F₄I₂·C₈H₈N₂S	C₆F₄I₂·2C₈H₈N₂S·2(H₂O)	C₆F₃I₃·C₈H₈N₂S
M_r	681.82	566.08	766.34	673.98
Crystal system, space group	Orthorhombic, Pnma	Triclinic, P $[\overline{1}]$	Triclinic, P $[\overline{1}]$	Monoclinic, P2₁/c
a, b, c (Å)	11.7547 (10), 8.3525 (7), 15.1077 (13)	4.5504 (5), 13.2872 (14), 13.8064 (14)	4.9088 (3), 11.4670 (8), 11.9686 (8)	15.191 (2), 5.0074 (7), 22.715 (3)
α, β, γ (°)	90, 90, 90	94.766 (4), 98.124 (4), 99.588 (4)	106.644 (2), 98.058 (2), 92.811 (2)	90, 97.460 (6), 90
V (Å³)	1483.3 (2)	809.97 (15)	636.27 (7)	1713.3 (4)
Z	4	2	1	4
μ (mm⁻¹)	8.52	4.05	2.69	5.62
Crystal size (mm)	0.30 × 0.14 × 0.11	0.19 × 0.07 × 0.04	0.31 × 0.11 × 0.08	0.26 × 0.04 × 0.04

Data collection
T_min, T_max	0.256, 0.746	0.636, 0.746	0.536, 0.746	0.582, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	32859, 1993, 1885	21426, 3704, 3174	31584, 3558, 3500	23258, 3971, 3039
R_int	0.055	0.042	0.036	0.069
(sin θ/λ)_max (Å⁻¹)	0.671	0.650	0.696	0.652

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.062, 1.26	0.026, 0.055, 1.24	0.014, 0.034, 1.18	0.047, 0.105, 1.22
No. of reflections	1993	3704	3558	3971
No. of parameters	89	217	184	217
No. of restraints	0	1	7	1
Δρ_max, Δρ_min (e Å⁻³)	1.25, −1.48	1.33, −1.06	0.44, −0.42	2.37, −1.89

	(MBZOX)·(1,2-F₄DIB)	(MBZOX)·(1,3-F₄DIB)	2(MBZOX)·(1,4-F₄DIB)	(MBZOX)·(1,3,5-F₃I₃B)
Crystal data
Chemical formula	C₆F₄I₂·C₇H₅NOS	C₆F₄I₂·C₇H₅NOS	C₆F₄I₂·2C₇H₅NOS	C₆F₃I₃·C₇H₅NOS
M_r	553.04	553.04	704.22	660.94
Crystal system, space group	Monoclinic, P2₁/n	Monoclinic, P2₁/c	Monoclinic, C2/c	Monoclinic, P2₁/c
a, b, c (Å)	13.7789 (12), 4.4129 (4), 25.252 (2)	15.1655 (8), 4.3803 (2), 23.0358 (12)	31.025 (4), 4.3159 (5), 19.061 (2)	14.9295 (7), 4.6119 (2), 23.5065 (12)
α, β, γ (°)	90, 96.337 (3), 90	90, 99.923 (2), 90	90, 114.434 (4), 90	90, 92.548 (2), 90
V (Å³)	1526.0 (2)	1507.36 (13)	2323.6 (5)	1616.90 (13)
Z	4	4	4	4
μ (mm⁻¹)	4.30	4.35	2.94	5.96
Crystal size (mm)	0.46 × 0.06 × 0.02	0.23 × 0.12 × 0.09	0.29 × 0.12 × 0.03	0.22 × 0.06 × 0.05

Data collection
T_min, T_max	0.578, 0.745	0.541, 0.746	0.637, 0.746	0.551, 0.745
No. of measured, independent and observed [I > 2σ(I)] reflections	12498, 3210, 2510	39610, 4625, 4119	25197, 2950, 2571	19413, 3348, 2845
R_int	0.066	0.042	0.047	0.050
(sin θ/λ)_max (Å⁻¹)	0.634	0.716	0.675	0.630

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.087, 1.11	0.022, 0.048, 1.16	0.028, 0.060, 1.32	0.029, 0.061, 1.22
No. of reflections	3210	4625	2950	3348
No. of parameters	203	203	149	203
No. of restraints	0	0	0	0
Δρ_max, Δρ_min (e Å⁻³)	1.58, −1.52	0.96, −1.35	1.54, −1.15	0.80, −0.77

	3(MBZTH)·4(1,2-F₄DIB)	(MBZTH)·(1,3-F₄DIB)	(MBZTH)·2(1,3-F₄DIB)	2(MBZTH)·(1,4-F₄DIB)
Crystal data
Chemical formula	4C₆F₄I₂·3C₇H₅NS₂	C₆F₄I₂·C₇H₅NS₂	4C₆F₄I₂·2C₇H₅NS₂	C₆F₄I₂·2C₇H₅NS₂
M_r	2109.16	569.10	1941.92	736.34
Crystal system, space group	Triclinic, P $[\overline{1}]$	Triclinic, P $[\overline{1}]$	Monoclinic, P2₁	Monoclinic, P2₁/n
a, b, c (Å)	7.9410 (8), 14.8483 (15), 24.641 (3)	7.2175 (4), 8.2675 (5), 14.4498 (9)	4.5581 (3), 34.358 (2), 15.6075 (10)	5.5057 (2), 15.6087 (7), 13.5194 (6)
α, β, γ (°)	79.264 (4), 87.104 (4), 82.784 (4)	97.936 (2), 91.297 (2), 109.178 (2)	90, 94.707 (2), 90	90, 94.259 (2), 90
V (Å³)	2830.9 (5)	804.44 (8)	2436.0 (3)	1158.61 (8)
Z	2	2	2	2
μ (mm⁻¹)	4.69	4.20	5.36	3.12
Crystal size (mm)	0.30 × 0.13 × 0.04	0.33 × 0.27 × 0.06	0.18 × 0.12 × 0.04	0.17 × 0.09 × 0.04

Data collection
T_min, T_max	0.570, 0.746	0.496, 0.746	0.568, 0.746	0.559, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	78566, 12466, 11325	27899, 4701, 4391	56285, 12660, 11766	22270, 3402, 2811
R_int	0.067	0.036	0.050	0.049
(sin θ/λ)_max (Å⁻¹)	0.642	0.706	0.678	0.706

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.220, 1.06	0.018, 0.044, 1.09	0.026, 0.046, 1.09	0.027, 0.057, 1.15
No. of reflections	12466	4701	12660	3402
No. of parameters	704	203	622	149
No. of restraints	66	0	2	0
Δρ_max, Δρ_min (e Å⁻³)	2.61, −1.48	1.08, −1.11	1.01, −0.71	0.90, −0.79
Absolute structure	–	–	Refined as an inversion twin	–
Absolute structure parameter	–	–	0.454 (15)	–

	(MBZTH)·(1,3,5-F₃I₃B)	(MBZTH)·(TIE)
Crystal data
Chemical formula	C₆F₃I₃·C₇H₅NS₂	C₂I₄·C₇H₅NS₂
M_r	677.00	698.86
Crystal system, space group	Monoclinic, P2₁/c	Triclinic, P $[\overline{1}]$
a, b, c (Å)	15.2665 (6), 4.7380 (2), 23.2215 (10)	7.4085 (6), 10.8180 (9), 11.1989 (10)
α, β, γ (°)	90, 93.139 (2), 90	66.616 (3), 70.765 (3), 70.792 (3)
V (Å³)	1677.15 (12)	757.20 (11)
Z	4	2
μ (mm⁻¹)	5.86	8.48
Crystal size (mm)	0.16 × 0.08 × 0.05	0.08 × 0.07 × 0.07

Data collection
T_min, T_max	0.610, 0.746	0.589, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	35222, 4212, 3611	22463, 3484, 3037
R_int	0.057	0.052
(sin θ/λ)_max (Å⁻¹)	0.669	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.024, 0.052, 1.18	0.029, 0.072, 1.13
No. of reflections	4212	3484
No. of parameters	203	159
No. of restraints	1	7
Δρ_max, Δρ_min (e Å⁻³)	0.67, −0.73	1.43, −1.76
computer programs: APEX3 (Bruker, 2017), SAINT (Bruker, 2017), SHELXT2018 (Sheldrick, 2015a ), SHELXL2018 (Sheldrick, 2015b ), Mercury (Macrae et al., 2020 ), and OLEX2 (Dolomanov et al., 2009 ).

3. 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 space group Pbcn with two unique molecules of IT and one molecule of 1,3-F₄DIB in the asymmetric unit (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 space group Pbca with one molecule each of IT and 1,3,5-F₃I₃B in the asymmetric unit. 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.

Table 2
Hydrogen-bond geometry (Å, °) for 2(IT)·(1,3-F₄DIB)

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⋯I2^iv	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⋯I1^v	0.99	3.20	3.9922 (16)	138
C5—H5B⋯F4	0.99	2.45	3.2774 (19)	140
C6—H6B⋯I1^vi	0.99	3.18	3.9223 (16)	133
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z]$ ; (ii) ; (iii) , ; (iv) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z]$ ; (v) $[-x+1, y, -z+{\script{1\over 2}}]$ ; (vi) $[x-{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Table 3
Halogen- and chalcogen-bond geometries (Å, °)

Compound		d(D⋯A)	R_XBⁱ	θ(C—D⋯A)	θ(D⋯A—C)	θ₁ – θ₂ⁱⁱ	ψⁱⁱⁱ
2(IT)·(1,3-F₄DIB)	I1⋯S1	3.2265 (6)	0.85	174.51 (4)	113.51 (5)	61.00	0.79
	I2⋯S1	3.2860 (5)	0.87	176.10 (4)	99.67 (5)	76.43	0.03
(IT)·(1,3,5-F₃I₃B)	I1⋯I3	3.8376 (6)	0.97	162.95 (8)	106.24 (7)	56.71	0.64
	I2⋯S1	3.1505 (8)	0.83	171.86 (7)	101.89 (10)	69.97	0.48
	I3⋯S1	3.1754 (8)	0.84	177.68 (8)	90.59 (9)	87.09	0.18
4(MBZIM)·3(1,3-F₄DIB)	I1⋯S3	3.3361 (10)	0.88	172.18 (8)	136.86 (8)	35.32	0.83
	I6⋯S2	3.2150 (9)	0.85	166.06 (8)	134.24 (8)	31.82	0.74
(MBZIM)·(1,4-F₄DIB)	I1⋯S1	3.2573 (9)	0.86	168.29 (6)	131.28 (8)	37.01	0.57
(MBZIM)·(TIE)	I1⋯S1	3.5368 (14)	0.94	173.83 (17)	71.37 (16)	102.46	0.66
	I3⋯S1	3.2702 (14)	0.87	177.05 (17)	118.15 (17)	58.90	0.64
(MMBZIM)·(1,2-F₄DIB)	I1⋯S1	3.6404 (10)	0.96	154.63 (12)	95.76 (13)	58.87	0.47
	I2⋯S1	3.2307 (11)	0.85	169.63 (11)	106.66 (15)	62.97	0.04
2(MMBZIM)·(1,4-F₄DIB)·2(H₂O)	I1⋯S1	3.2516 (4)	0.86	169.16 (4)	96.12 (4)	73.04	0.37
(MMBZIM)·(1,3,5-F₃I₃B)	I2⋯S1	3.474 (2)	0.92	164.1 (3)	92.1 (3)	72.0	0.71
	I3⋯S1	3.463 (2)	0.92	176.7 (3)	96.5 (3)	80.2	0.50
(MBZOX)·(1,2-F₄DIB)	I2⋯S1	3.2853 (19)	0.87	166.65 (19)	105.4 (3)	61.3	0.19
(MBZOX)·(1,3-F₄DIB)	I1⋯S1	3.4132 (7)	0.90	174.53 (6)	105.63 (8)	68.90	0.19
	I2⋯S1	3.6787 (6)	0.97	159.40 (6)	92.48 (7)	66.92	0.66
	S1⋯I1	3.7536 (7)	0.99	160.34 (7)	105.80 (6)	54.54	0.53
2(MBZOX)·(1,4-F₄DIB)	I1⋯S1	3.2287 (11)	0.85	174.60 (9)	109.39 (13)	65.21	0.74
(MBZOX)·(1,3,5-F₃I₃B)	I1⋯S1	3.4114 (14)	0.90	171.55 (13)	100.14 (19)	71.41	0.14
	I2⋯I3	3.9110 (7)	0.99	147.22 (13)	79.55 (13)	67.67	0.62
	I3⋯S1	3.6774 (13)	0.97	157.67 (15)	95.79 (16)	61.88	0.67
	S1⋯I1	3.7385 (14)	0.99	163.12 (17)	98.99 (14)	64.13	0.44
3(MBZTH)·4(1,2-F₄DIB)	I1⋯S5	3.380 (4)	0.89	177.9 (4)	113.3 (5)	64.6	0.81
	I2⋯S5	3.353 (4)	0.89	163.7 (4)	128.9 (5)	34.8	0.61
	I3⋯S3	3.371 (5)	0.89	169.0 (4)	96.4 (7)	72.6	0.02
	I4⋯S3	3.754 (4)	0.99	173.7 (4)	100.5 (6)	73.2	0.76
	I5⋯S1	3.380 (4)	0.89	177.9 (4)	113.3 (5)	64.6	0.81
	I6⋯I7	3.8766 (14)	0.95	170.5 (4)	118.1 (4)	52.4	0.73
	I6⋯S1	3.391 (5)	0.90	168.1 (4)	111.3 (6)	56.8	0.76
(MBZTH)·(1,3-F₄DIB)	I1⋯S1	3.3724 (5)	0.89	168.06 (6)	120.18 (6)	47.88	0.64
	I2⋯S1	3.4140 (5)	0.90	157.68 (4)	106.00 (5)	51.68	0.66
(MBZTH)·2(1,3-F₄DIB)	I1⋯S3	3.3426 (17)	0.88	168.34 (18)	103.3 (2)	65.0	0.25
	I2⋯S2	3.7429 (17)	0.99	152.94 (18)	121.7 (4)ⁱⁱⁱ	31.2	0.23
	I3⋯S1	3.3548 (18)	0.89	166.60 (17)	100.3 (2)	66.3	0.64
	I4⋯S4	3.6744 (17)	0.97	148.74 (18)	118.4 (4)ⁱⁱⁱ	30.4	0.65
	I5⋯I4	3.7971 (10)	0.96	163.30 (19)	82.92 (18)	80.38	0.52
	I8⋯I2	3.7950 (9)	0.96	170.03 (18)	84.69 (18)	85.34	0.71
2(MBZTH)·(1,4-F₄DIB)	I1⋯S1	3.3013 (7)	0.87	178.16 (7)	103.84 (10)	74.32	0.60
(MBZTH)·(1,3,5-F₃I₃B)	I1⋯S1	3.4551 (10)	0.91	169.01 (9)	97.89 (13)	71.12	0.71
	S2⋯I3	3.7777 (10)	1.00	158.73 (12)	117.64 (10)	41.09	0.52
(MBZTH)·(TIE)	I1⋯I3	3.9459 (7)	1.00	171.07 (14)	70.7 (3)	100.4	0.55
	I3⋯S1	3.2826 (13)	0.87	162.1 (3)	122.51 (19)	39.6	0.41
	I4⋯S1	3.6514 (19)	0.97	161.9 (3)	77.0 (2)	84.9	0.46
Notes: (i) R_XB = d(X⋯Y)/Σd(vdW), the ratio of the distance between the donor atom (i.e. I) and the acceptor atom (i.e. S) to the sum of their van der Waals (vdW) radii (S = 1.80 Å and I = 1.98 Å) (Auffinger et al., 2004 ). (ii) θ₁ – θ₂ = \|{[θ(C—D⋯A)] – [θ(D⋯A—C)]}\|. (iii) Linearity parameter (Setter et al., 2020 ).

Table 4
Hydrogen-bond geometry (Å, °) for (IT)·(1,3,5-F₃I₃B)

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) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Figure 2
Cocrystalline structures containing IT. Hydrogen and halogen bonding are indicated by black dotted lines. Displacement ellipsoids are drawn at the 50% probability level. H atoms, except those bound to N atoms, have been omitted for clarity.

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 space group P $[\overline{1}]$ , with four unique molecules of MBZIM and three molecules of 1,3-F₄DIB in the asymmetric unit. 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 space group P2₁/c, with one molecule each of both MBZIM and 1,4-F₄DIB in the asymmetric unit. 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.

Table 5
Hydrogen-bond geometry (Å, °) for 4(MBZIM)·3(1,3-F₄DIB)

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⋯F36^iv	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) ; (iii) ; (iv) .

Table 6
Hydrogen-bond geometry (Å, °) for (MBZIM)·(1,4-F₄DIB)

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) ; (ii) .

Figure 3
Cocrystal structures containing MBZIM. Hydrogen and halogen bonding are indicated by black dotted lines. Displacement ellipsoids are drawn at the 50% probability level. H atoms, except those bound to N atoms, have been omitted for clarity.

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 space group Pnma, with one molecule each of MBZIM and TIE in the asymmetric unit. 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.

Table 7
Hydrogen-bond geometry (Å, °) for (MBZIM)·(TIE)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—HN1⋯S1ⁱ	0.87 (5)	2.47 (5)	3.335 (3)	178 (5)
C3—H3⋯I1ⁱⁱ	0.95	3.28	3.881 (4)	123
Symmetry codes: (i) ; (ii) $[-x+{\script{3\over 2}}, -y+1, z+{\script{1\over 2}}]$ .

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 space group P $[\overline{1}]$ , with one molecule each of MMBZIM and 1,2-F₄DIB in the asymmetric unit (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.

Table 8
Hydrogen-bond geometry (Å, °) for (MMBZIM)·(1,2-F₄DIB)

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) ; (ii) x, y, z+1.

Figure 4
Cocrystalline structures containing MMBZIM. Hydrogen and halogen bonding are indicated by black dotted lines. Displacement ellipsoids are drawn at the 50% probability level. H atoms, except those bound to N atoms, have been omitted for clarity.

Isolated as a hydrated cocrystal from adventitious water, 2(MMBZIM)·(1,4-F4DIB)·2(H₂O) crystallizes in the triclinic space group P $[\overline{1}]$ with one molecule each of MMBZIM and H₂O, as well as half a molecule of 1,4-F₄DIB, in the asymmetric unit. 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.

Table 9
Hydrogen-bond geometry (Å, °) for 2(MMBZIM)·(1,4-F₄DIB)·2(H₂O)

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⋯S1ⁱ	0.88 (2)	2.57 (2)	3.4211 (13)	164 (2)
C4—H4⋯I1ⁱⁱ	0.95	3.03	3.9505 (14)	164
O1—H1AO⋯O1ⁱⁱⁱ	0.88 (2)	1.85 (2)	2.708 (3)	163 (4)
O1—H1BO⋯O1^iv	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⋯S1ⁱⁱⁱ	0.87 (2)	2.65 (2)	3.4251 (13)	149 (3)
Symmetry codes: (i) ; (ii) x, y+1, z; (iii) ; (iv) .

Finally, the combination of 1,3,5-F₃I₃B and MMBZIM resulted in the cocrystal (MMBZIM)·(1,3,5-F₃I₃B), refined in the monoclinic space group P2₁/c with one unique molecule of each component in the asymmetric unit. 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.

Table 10
Hydrogen-bond geometry (Å, °) for (MMBZIM)·(1,3,5-F₃I₃B)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—HN1⋯S1ⁱ	0.86 (2)	2.57 (3)	3.426 (7)	173 (10)
N2—HN2⋯I2ⁱⁱ	0.85 (8)	3.02 (8)	3.657 (7)	133 (7)
C3—H3⋯I3ⁱⁱⁱ	0.95	3.12	4.035 (9)	163
C6—H6⋯I1^iv	0.95	3.14	3.927 (8)	142
Symmetry codes: (i) ; (ii) ; (iii) x, y+1, z; (iv) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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 space group P2₁/n, with one unique molecule each of MBZOX and 1,2-F₄DIB in the asymmetric unit. 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 space group P2₁/c, with one molecule each of MBZOX and 1,3-F₄DIB in the asymmetric unit, 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 space group 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 space group P2₁/c, with one molecule each of MBZOX and 1,3,5-F₃I₃B in the asymmetric unit. 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 substructure. 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.

Table 11
Hydrogen-bond geometry (Å, °) for (MBZOX)·(1,2-F₄DIB)

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) ; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Table 12
Hydrogen-bond geometry (Å, °) for (MBZOX)·(1,3-F₄DIB)

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) ; (ii) $[-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Table 13
Hydrogen-bond geometry (Å, °) for 2(MBZOX)·(1,4-F₄DIB)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—HN1⋯S1ⁱ	0.87 (4)	2.45 (4)	3.316 (3)	178 (4)
C3—H3⋯I1ⁱⁱ	0.95	3.16	4.066 (3)	159
Symmetry codes: (i) ; (ii) .

Table 14
Hydrogen-bond geometry (Å, °) for (MBZOX)·(1,3,5-F₃I₃B)

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) ; (ii) ; (iii) $[x, -y+{\script{5\over 2}}]$ , $[z-{\script{1\over 2}}]$ .

Figure 5
Cocrystalline structures containing MBZOX. Hydrogen and halogen bonding are indicated by black dotted lines. Displacement ellipsoids are drawn at the 50% probability level. H atoms, except those bound to N atoms, have been omitted for clarity.

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 space group P $[\overline{1}]$ , with three molecules of MBZTH and four molecules of 1,2-F₄DIB in the asymmetric unit. 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.

Table 15
Hydrogen-bond geometry (Å, °) for 3(MBZTH)·4(1,2-F₄DIB)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—HN2⋯S1	0.88	2.45	3.326 (14)	174
N1—HN1⋯S3	0.88	2.40	3.266 (14)	169
C6—H6⋯F10ⁱ	0.95	2.60	3.29 (2)	130
N3—HN3⋯S5ⁱⁱ	0.88	2.42	3.290 (14)	170
C17—H17⋯F16	0.95	2.30	3.232 (18)	166
C20—H20⋯F2	0.95	2.53	3.128 (18)	121
C20—H20⋯F3	0.95	2.54	3.181 (17)	125
Symmetry codes: (i) ; (ii) .

Figure 6
Cocrystalline structures containing MBZTH. Hydrogen and halogen bonding are indicated by black dotted lines. Displacement ellipsoids are drawn at the 50% probability level. H atoms, except those bound to N atoms, have been omitted for clarity.

The packing motif of (MBZTH)·(1,3-F₄DIB), refined in the triclinic space group P $[\overline{1}]$ , with one molecule each of MBZTH and 1,3-F₄DIB within the asymmetric unit, 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 space group P2₁, the asymmetric unit 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.

Table 16
Hydrogen-bond geometry (Å, °) for (MBZTH)·(1,3-F₄DIB)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—HN1⋯S1ⁱ	0.87 (3)	2.45 (3)	3.3120 (15)	175 (2)
Symmetry code: (i) .

Table 17
Hydrogen-bond geometry (Å, °) for (MBZTH)·2(1,3-F₄DIB)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—HN1⋯S3	0.89 (6)	2.51 (6)	3.376 (6)	165 (5)
C3—H3⋯I1	0.95	3.10	3.976 (7)	154
N2—HN2⋯S1	0.85 (3)	2.52 (3)	3.360 (6)	169 (7)
C10—H10⋯I3ⁱ	0.95	3.09	4.006 (6)	161
Symmetry code: (i) x, y, z+1.

The packing motif of 2(MBZTH)·(1,4-F₄DIB), refined in the monoclinic space group P2₁/n, with one complete molecule of MBZTH and one-half of a molecule of 1,4-F₄DIB in the asymmetric unit, 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 space group P2₁/c, with one unique molecule each of both MBZTH and 1,3,5-F₃I₃B in the asymmetric unit. 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 space group P $[\overline{1}]$ with one unique molecule of MBZTH and two unique half molecules of TIE in the asymmetric unit. 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.

Table 18
Hydrogen-bond geometry (Å, °) for 2(MBZTH)·(1,4-F₄DIB)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—HN1⋯S1ⁱ	0.78 (3)	2.60 (3)	3.369 (2)	170 (3)
C3—H3⋯F1ⁱⁱ	0.95	2.50	3.333 (3)	146
C6—H6⋯F2ⁱⁱⁱ	0.95	2.44	3.357 (3)	162
Symmetry codes: (i) ; (ii) ; (iii) $[-x+{\script{3\over 2}}]$ , $[y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Table 19
Hydrogen-bond geometry (Å, °) for (MBZTH)·(1,3,5-F₃I₃B)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—HN1⋯S1ⁱ	0.86 (2)	2.54 (2)	3.389 (3)	172 (4)
C3—H3⋯I1ⁱⁱ	0.95	3.03	3.928 (4)	159
Symmetry codes: (i) ; (ii) .

Table 20
Hydrogen-bond geometry (Å, °) for (MBZTH)·(TIE)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—HN1⋯S1ⁱ	0.85 (2)	2.43 (2)	3.275 (5)	170 (6)
Symmetry code: (i) .

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 R_XB 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 hybridization 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

CCDC references: 2194060; 2194061; 2194062; 2194063; 2194064; 2194065; 2194066; 2194067; 2194068; 2194069; 2194070; 2194071; 2194072; 2194073; 2194074; 2194075; 2194076; 2194077

Crystal structure: 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: https://doi.org/10.1107/S2053229622009548/qw3002sup1.cif

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

Computing details top

For all structures, data collection: APEX3 (Bruker, 2017); cell refinement: 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).

1,2,3,5-Tetrafluoro-4,6-diiodobenzene–imidazolidine-2-thione (1/2) (2IT_13F4DIB) top

Crystal data top

C₆F₄I₂·2C₃H₆N₂S	D_x = 2.193 Mg m⁻³
M_r = 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

Data collection top

Bruker D8 Venture Photon 2 diffractometer	5198 reflections with I > 2σ(I)
Radiation source: Incoatec IµS	R_int = 0.035
φ and ω scans	θ_max = 30.1°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2017)	h = −22→22
T_min = 0.639, T_max = 0.746	k = −12→12
112821 measured reflections	l = −36→31
5376 independent reflections

Refinement top

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(F_o²) + (0.0054P)² + 3.3158P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.032	(Δ/σ)_max = 0.003
S = 1.25	Δρ_max = 0.42 e Å⁻³
5376 reflections	Δρ_min = −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)

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···I2^iv	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···I1^v	0.99	3.20	3.9922 (16)	138
C5—H5B···F4	0.99	2.45	3.2774 (19)	140
C6—H6B···I1^vi	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.

Imidazolidine-2-thione–1,3,5-trifluoro-2,4,6-triiodobenzene (1/1) (IT_135F3I3B) top

Crystal data top

C₆F₃I₃·C₃H₆N₂S	D_x = 2.797 Mg m⁻³
M_r = 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

Data collection top

Bruker D8 Venture Photon 2 diffractometer	3220 reflections with I > 2σ(I)
Radiation source: Incoatec IµS	R_int = 0.043
φ and ω scans	θ_max = 28.3°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2017)	h = −24→24
T_min = 0.563, T_max = 0.746	k = −9→9
49179 measured reflections	l = −28→29
3615 independent reflections

Refinement top

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(F_o²) + (0.0114P)² + 5.9439P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.040	(Δ/σ)_max = 0.002
S = 1.11	Δρ_max = 0.57 e Å⁻³
3615 reflections	Δρ_min = −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)

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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.

1H-1,3-Benzodiazole-2-thiol–1,2,3,5-tetrafluoro-4,6-diiodobenzene (4/3) (4MBZIM_313F4DIB) top

Crystal data top

3C₆F₄I₂·4C₇H₆N₂S	Z = 2
M_r = 1806.37	F(000) = 1692
Triclinic, P1	D_x = 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

Data collection top

Bruker D8 Venture Photon 2 diffractometer	10558 reflections with I > 2σ(I)
Radiation source: Incoatec IµS	R_int = 0.056
φ and ω scans	θ_max = 27.6°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2017)	h = −10→10
T_min = 0.668, T_max = 0.746	k = −23→23
118524 measured reflections	l = −24→24
12297 independent reflections

Refinement top

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(F_o²) + (0.0068P)² + 2.3276P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.002
12297 reflections	Δρ_max = 0.52 e Å⁻³
717 parameters	Δρ_min = −0.75 e Å⁻³
8 restraints

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···F36^iv	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.

1H-1,3-Benzodiazole-2-thiol–1,2,4,5-tetrafluoro-3,6-diiodobenzene (1/1) (MBZIM_14F4DIB) top

Crystal data top

C₆F₄I₂·C₇H₆N₂S	F(000) = 1024
M_r = 552.06	D_x = 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

Data collection top

Bruker D8 Venture Photon 2 diffractometer	4211 reflections with I > 2σ(I)
Radiation source: Incoatec IµS	R_int = 0.050
φ and ω scans	θ_max = 30.2°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2017)	h = −7→7
T_min = 0.501, T_max = 0.746	k = −46→46
45583 measured reflections	l = −11→11
4579 independent reflections

Refinement top

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(F_o²) + (0.0059P)² + 1.8833P] where P = (F_o² + 2F_c²)/3
S = 1.12	(Δ/σ)_max = 0.002
4579 reflections	Δρ_max = 0.49 e Å⁻³
207 parameters	Δρ_min = −0.67 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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.

1H-1,3-Benzodiazole-2-thiol–1,1,2,2-tetraiodoethene (1/1) (MBZIM_TIE) top

Crystal data top

C₂I₄·C₇H₆N₂S	D_x = 3.053 Mg m⁻³
M_r = 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

Data collection top

Bruker D8 Venture Photon 2 diffractometer	1885 reflections with I > 2σ(I)
Radiation source: Incoatec IµS	R_int = 0.055
φ and ω scans	θ_max = 28.5°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2017)	h = −15→15
T_min = 0.256, T_max = 0.746	k = −11→11
32859 measured reflections	l = −20→20
1993 independent reflections

Refinement top

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(F_o²) + (0.0213P)² + 6.7951P] where P = (F_o² + 2F_c²)/3
S = 1.25	(Δ/σ)_max = 0.001
1993 reflections	Δρ_max = 1.25 e Å⁻³
89 parameters	Δρ_min = −1.48 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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.

Hydrogen-bond geometry (Å, º) top

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.

5-Methyl-1H-1,3-benzodiazole-2-thiol–1,2,3,4-tetrafluoro-5,6-diiodobenzene (1/1) (MMBZIM_12F4DIB) top

Crystal data top

C₆F₄I₂·C₈H₈N₂S	Z = 2
M_r = 566.08	F(000) = 528
Triclinic, P1	D_x = 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

Data collection top

Bruker D8 Venture Photon 2 diffractometer	3174 reflections with I > 2σ(I)
Radiation source: Incoatec IµS	R_int = 0.042
φ and ω scans	θ_max = 27.5°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2017)	h = −5→5
T_min = 0.636, T_max = 0.746	k = −17→17
21426 measured reflections	l = −17→17
3704 independent reflections

Refinement top

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(F_o²) + 2.2494P] where P = (F_o² + 2F_c²)/3
S = 1.24	(Δ/σ)_max < 0.001
3704 reflections	Δρ_max = 1.33 e Å⁻³
217 parameters	Δρ_min = −1.06 e Å⁻³
1 restraint

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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.

5-Methyl-1H-1,3-benzodiazole-2-thiol–1,2,4,5-tetrafluoro-3,6-diiodobenzene–water (2/1/2) (2MMBZIM_14F4DIB_2H2O) top

Crystal data top

C₆F₄I₂·2C₈H₈N₂S·2(H₂O)	Z = 1
M_r = 766.34	F(000) = 370
Triclinic, P1	D_x = 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

Data collection top

Bruker D8 Venture Photon 2 diffractometer	3500 reflections with I > 2σ(I)
Radiation source: Incoatec IµS	R_int = 0.036
φ and ω scans	θ_max = 29.7°, θ_min = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2017)	h = −6→6
T_min = 0.536, T_max = 0.746	k = −15→15
31584 measured reflections	l = −16→16
3558 independent reflections

Refinement top

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(F_o²) + 0.4884P] where P = (F_o² + 2F_c²)/3
S = 1.18	(Δ/σ)_max = 0.002
3558 reflections	Δρ_max = 0.44 e Å⁻³
184 parameters	Δρ_min = −0.42 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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.

Hydrogen-bond geometry (Å, º) top

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···O1^iv	0.88 (2)	1.85 (2)	2.708 (3)	163 (4)
O1—H1BO···O1^v	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···S1^iv	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.

5-Methyl-1H-1,3-benzodiazole-2-thiol–1,3,5-trifluoro-2,4,6-\ triiodobenzene (1/1) (MMBZIM_135F3I3B) top

Crystal data top

C₆F₃I₃·C₈H₈N₂S	F(000) = 1232
M_r = 673.98	D_x = 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

Data collection top

Bruker D8 Venture Photon 2 diffractometer	3039 reflections with I > 2σ(I)
Radiation source: Incoatec IµS	R_int = 0.069
φ and ω scans	θ_max = 27.6°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2017)	h = −19→19
T_min = 0.582, T_max = 0.746	k = −6→6
23258 measured reflections	l = −29→29
3971 independent reflections

Refinement top

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(F_o²) + 32.9663P] where P = (F_o² + 2F_c²)/3
S = 1.22	(Δ/σ)_max < 0.001
3971 reflections	Δρ_max = 2.36 e Å⁻³
215 parameters	Δρ_min = −1.89 e Å⁻³
1 restraint

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···I1^iv	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.

1,3-Benzoxazole-2-thiol–1,2,3,4-tetrafluoro-5,6-diiodobenzene (1/1) (MBZOX_12F4DIB) top

Crystal data top

C₆F₄I₂·C₇H₅NOS	F(000) = 1024
M_r = 553.04	D_x = 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

Data collection top

Bruker D8 Venture Photon 2 diffractometer	2510 reflections with I > 2σ(I)
Radiation source: Incoatec IµS	R_int = 0.066
φ and ω scans	θ_max = 26.8°, θ_min = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2017)	h = −17→17
T_min = 0.578, T_max = 0.745	k = −5→5
12498 measured reflections	l = −31→31
3210 independent reflections

Refinement top

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(F_o²) + (0.0191P)² + 7.3427P] where P = (F_o² + 2F_c²)/3
S = 1.11	(Δ/σ)_max = 0.001
3210 reflections	Δρ_max = 1.58 e Å⁻³
203 parameters	Δρ_min = −1.52 e Å⁻³
0 restraints

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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.

1,3-Benzoxazole-2-thiol–1,2,3,5-tetrafluoro-4,6-diiodobenzene (1/1) (MBZOX_13F4DIB) top

Crystal data top

C₆F₄I₂·C₇H₅NOS	F(000) = 1024
M_r = 553.04	D_x = 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

Data collection top

Bruker D8 Venture Photon 2 diffractometer	4119 reflections with I > 2σ(I)
Radiation source: Incoatec IµS	R_int = 0.042
φ and ω scans	θ_max = 30.6°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2017)	h = −21→21
T_min = 0.541, T_max = 0.746	k = −6→6
39610 measured reflections	l = −32→32
4625 independent reflections

Refinement top

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(F_o²) + (0.0088P)² + 2.2764P] where P = (F_o² + 2F_c²)/3
S = 1.16	(Δ/σ)_max = 0.002
4625 reflections	Δρ_max = 0.96 e Å⁻³
203 parameters	Δρ_min = −1.35 e Å⁻³
0 restraints

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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.

1,3-Benzoxazole-2-thiol–1,2,4,5-tetrafluoro-3,6-diiodobenzene (2/1) (2MBZOX_14F4DIB) top

Crystal data top

C₆F₄I₂·2C₇H₅NOS	F(000) = 1336
M_r = 704.22	D_x = 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

Data collection top

Bruker D8 Venture Photon 2 diffractometer	2571 reflections with I > 2σ(I)
Radiation source: Incoatec IµS	R_int = 0.047
φ and ω scans	θ_max = 28.7°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2017)	h = −41→41
T_min = 0.637, T_max = 0.746	k = −5→5
25197 measured reflections	l = −25→25
2950 independent reflections

Refinement top

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(F_o²) + 11.7646P] where P = (F_o² + 2F_c²)/3
S = 1.32	(Δ/σ)_max = 0.002
2950 reflections	Δρ_max = 1.54 e Å⁻³
149 parameters	Δρ_min = −1.15 e Å⁻³
0 restraints

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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.

Hydrogen-bond geometry (Å, º) top

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.

1,3-Benzoxazole-2-thiol–1,3,5-trifluoro-2,4,6-triiodobenzene (1/1) (MBZOX_135F3I3B) top

Crystal data top

C₆F₃I₃·C₇H₅NOS	F(000) = 1200
M_r = 660.94	D_x = 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

Data collection top

Bruker D8 Venture Photon 2 diffractometer	2845 reflections with I > 2σ(I)
Radiation source: Incoatec IµS	R_int = 0.050
φ and ω scans	θ_max = 26.6°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2017)	h = −18→18
T_min = 0.551, T_max = 0.745	k = −5→5
19413 measured reflections	l = −29→29
3348 independent reflections

Refinement top

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(F_o²) + (0.0015P)² + 8.0148P] where P = (F_o² + 2F_c²)/3
S = 1.22	(Δ/σ)_max = 0.002
3348 reflections	Δρ_max = 0.80 e Å⁻³
203 parameters	Δρ_min = −0.77 e Å⁻³
0 restraints

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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.

1,3-Benzothiazole-2-thiol)–1,2,3,4-tetrafluoro-5,6-diiodobenzene (3/4) (3MBZTH_412F4DIB) top

Crystal data top

4C₆F₄I₂·3C₇H₅NS₂	V = 2830.9 (5) Å³
M_r = 2109.16	Z = 2
Triclinic, P1	F(000) = 1940
a = 7.9410 (8) Å	D_x = 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

Data collection top

Bruker D8 Venture Photon 2 diffractometer	11325 reflections with I > 2σ(I)
Radiation source: Incoatec IµS	R_int = 0.067
φ and ω scans	θ_max = 27.2°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2017)	h = −10→10
T_min = 0.570, T_max = 0.746	k = −19→19
78566 measured reflections	l = −31→31
12466 independent reflections

Refinement top

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(F_o²) + (0.1285P)² + 109.2112P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
12466 reflections	Δρ_max = 2.61 e Å⁻³
704 parameters	Δρ_min = −1.48 e Å⁻³

Special details top

Refinement. Refined as a 2-component twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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	−3 (2)
F1—C24—C25—C26	179.3 (13)	C37—C38—C39—F12	178.2 (14)
F2—C25—C26—F3	1 (2)	C37—C38—C39—C34	1 (2)
F2—C25—C26—C27	179.9 (13)	C39—C34—C35—I6	−174.6 (11)
F3—C26—C27—F4	−2 (2)	C39—C34—C35—C36	3 (2)
F3—C26—C27—C22	−179.9 (13)	I7—C40—C41—I8	−5.3 (19)
C8—S4—C9—C10	−178.3 (16)	I7—C40—C41—C42	179.9 (13)
C8—S4—C9—C14	−0.2 (12)	I7—C40—C45—F16	6 (2)
C8—N2—C14—C9	−1 (2)	I7—C40—C45—C44	−178.8 (12)
C8—N2—C14—C13	178.0 (16)	I8—C41—C42—F13	8 (2)
C9—S4—C8—S3	−179.6 (10)	I8—C41—C42—C43	−178.7 (14)
C9—S4—C8—N2	−0.1 (12)	F13—C42—C43—F14	−5 (3)
C9—C10—C11—C12	6 (3)	F13—C42—C43—C44	178.0 (15)
C10—C9—C14—N2	178.8 (14)	F14—C43—C44—F15	−1 (3)
C10—C9—C14—C13	0 (2)	F14—C43—C44—C45	−179.9 (15)
C10—C11—C12—C13	−7 (3)	F15—C44—C45—F16	−3 (2)
C11—C12—C13—C14	4 (3)	F15—C44—C45—C40	−178.3 (15)
C12—C13—C14—N2	−178.8 (16)	C40—C41—C42—F13	−176.5 (16)
C12—C13—C14—C9	0 (2)	C40—C41—C42—C43	−4 (3)
C14—N2—C8—S3	179.9 (12)	C41—C40—C45—F16	−175.7 (14)
C14—N2—C8—S4	0.4 (17)	C41—C40—C45—C44	0 (2)
C14—C9—C10—C11	−3 (2)	C41—C42—C43—F14	−178.9 (17)
C22—C23—C24—F1	−179.2 (14)	C41—C42—C43—C44	4 (3)
C22—C23—C24—C25	−1 (2)	C42—C43—C44—F15	176.2 (16)
C23—C22—C27—F4	−179.1 (13)	C42—C43—C44—C45	−3 (3)
C23—C22—C27—C26	−1 (2)	C43—C44—C45—F16	176.8 (15)
C23—C24—C25—F2	−179.8 (14)	C43—C44—C45—C40	1 (2)
C23—C24—C25—C26	1 (2)	C45—C40—C41—I8	176.1 (11)
C24—C25—C26—F3	179.9 (13)	C45—C40—C41—C42	1 (2)
C24—C25—C26—C27	−1 (2)	S2—C2—C3—C4	179.7 (14)
C25—C26—C27—F4	179.1 (14)	S2—C2—C7—N1	−3.3 (18)
C25—C26—C27—C22	1 (2)	S2—C2—C7—C6	179.8 (14)
C27—C22—C23—I2	−177.4 (11)	C1—S2—C2—C3	178.1 (16)
C27—C22—C23—C24	1 (2)	C1—S2—C2—C7	2.8 (13)
I3—C28—C29—I4	5.1 (19)	C1—N1—C7—C2	2 (2)
I3—C28—C29—C30	−175.4 (11)	C1—N1—C7—C6	179.0 (15)
I3—C28—C33—F8	−3 (2)	C2—S2—C1—S1	178.3 (10)
I3—C28—C33—C32	177.7 (13)	C2—S2—C1—N1	−1.8 (12)
I4—C29—C30—F5	0 (2)	C2—C3—C4—C5	4 (3)
I4—C29—C30—C31	179.0 (12)	C3—C2—C7—N1	−178.9 (15)
F5—C30—C31—F6	0 (2)	C3—C2—C7—C6	4 (3)
F5—C30—C31—C32	177.2 (14)	C3—C4—C5—C6	−2 (3)
F6—C31—C32—F7	−2 (2)	C4—C5—C6—C7	0 (3)
F6—C31—C32—C33	−179.0 (15)	C5—C6—C7—N1	−177.9 (17)
F7—C32—C33—F8	0 (2)	C5—C6—C7—C2	−1 (3)
F7—C32—C33—C28	179.6 (15)	C7—N1—C1—S1	−179.9 (12)
C28—C29—C30—F5	−179.4 (14)	C7—N1—C1—S2	0.2 (16)
C28—C29—C30—C31	0 (2)	C7—C2—C3—C4	−6 (3)
C29—C28—C33—F8	−179.5 (14)	S6—C16—C17—C18	−178.4 (13)
C29—C28—C33—C32	1 (2)	S6—C16—C21—N3	−4.0 (16)
C29—C30—C31—F6	−179.1 (15)	S6—C16—C21—C20	178.7 (12)
C29—C30—C31—C32	−2 (2)	C15—S6—C16—C17	176.4 (16)
C30—C31—C32—F7	−179.3 (15)	C15—S6—C16—C21	2.5 (12)
C30—C31—C32—C33	4 (2)	C15—N3—C21—C16	4.0 (19)
C31—C32—C33—F8	177.3 (15)	C15—N3—C21—C20	−178.8 (15)
C31—C32—C33—C28	−3 (3)	C16—S6—C15—S5	179.3 (10)
C33—C28—C29—I4	−178.6 (11)	C16—S6—C15—N3	−0.3 (12)
C33—C28—C29—C30	1 (2)	C16—C17—C18—C19	5 (3)
I5—C34—C35—I6	0.3 (19)	C17—C16—C21—N3	−178.6 (14)
I5—C34—C35—C36	178.4 (11)	C17—C16—C21—C20	4 (2)
I5—C34—C39—F12	6 (2)	C17—C18—C19—C20	−4 (3)
I5—C34—C39—C38	−176.1 (12)	C18—C19—C20—C21	3 (3)
I6—C35—C36—F9	−2.2 (19)	C19—C20—C21—N3	−180.0 (15)
I6—C35—C36—C37	172.5 (12)	C19—C20—C21—C16	−3 (2)
F9—C36—C37—F10	0 (2)	C21—N3—C15—S5	178.4 (11)
F9—C36—C37—C38	−179.9 (14)	C21—N3—C15—S6	−2.0 (17)
F10—C37—C38—F11	−1 (2)	C21—C16—C17—C18	−5 (2)
F10—C37—C38—C39	177.6 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—HN2···S1	0.88	2.45	3.326 (14)	174
N1—HN1···S3	0.88	2.40	3.266 (14)	169
C6—H6···F10ⁱ	0.95	2.60	3.29 (2)	130
N3—HN3···S5ⁱⁱ	0.88	2.42	3.290 (14)	170
C17—H17···F16	0.95	2.30	3.232 (18)	166
C20—H20···F2	0.95	2.53	3.128 (18)	121
C20—H20···F3	0.95	2.54	3.181 (17)	125

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

1,3-Benzothiazole-2-thiol–1,2,3,5-tetrafluoro-4,6-diiodobenzene (1/1) (MBZTH_13F4DIB) top

Crystal data top

C₆F₄I₂·C₇H₅NS₂	Z = 2
M_r = 569.10	F(000) = 528
Triclinic, P1	D_x = 2.349 Mg m⁻³
a = 7.2175 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.2675 (5) Å	Cell parameters from 9969 reflections
c = 14.4498 (9) Å	θ = 2.6–30.1°
α = 97.936 (2)°	µ = 4.20 mm⁻¹
β = 91.297 (2)°	T = 100 K
γ = 109.178 (2)°	Plate, colourless
V = 804.44 (8) Å³	0.33 × 0.27 × 0.06 mm

Data collection top

Bruker D8 Venture Photon 2 diffractometer	4391 reflections with I > 2σ(I)
Radiation source: Incoatec IµS	R_int = 0.036
φ and ω scans	θ_max = 30.1°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2017)	h = −10→10
T_min = 0.496, T_max = 0.746	k = −11→11
27899 measured reflections	l = −20→20
4701 independent reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.018	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.044	w = 1/[σ²(F_o²) + (0.0115P)² + 0.801P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max = 0.002
4701 reflections	Δρ_max = 1.08 e Å⁻³
203 parameters	Δρ_min = −1.11 e Å⁻³
0 restraints

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
I1	0.21928 (2)	0.04578 (2)	0.73577 (2)	0.02046 (4)
I2	0.40359 (2)	0.24728 (2)	0.35536 (2)	0.02203 (4)
F1	0.17793 (18)	0.11993 (18)	0.52937 (9)	0.0275 (3)
F2	0.83758 (19)	0.35764 (19)	0.45929 (9)	0.0317 (3)
F3	0.95882 (18)	0.33437 (18)	0.63449 (9)	0.0304 (3)
F4	0.69486 (18)	0.19590 (15)	0.75449 (8)	0.0219 (2)
C8	0.4287 (3)	0.1563 (2)	0.64457 (13)	0.0174 (3)
C9	0.3711 (3)	0.1745 (3)	0.55526 (13)	0.0192 (4)
C10	0.5038 (3)	0.2421 (2)	0.49121 (13)	0.0184 (3)
C11	0.7028 (3)	0.2946 (3)	0.51885 (14)	0.0207 (4)
C12	0.7664 (3)	0.2813 (3)	0.60795 (14)	0.0209 (4)
C13	0.6289 (3)	0.2109 (2)	0.66928 (12)	0.0180 (3)
S1	0.82694 (7)	0.91230 (6)	0.86324 (3)	0.01549 (8)
S2	0.65916 (6)	0.53019 (5)	0.86630 (3)	0.01339 (8)
N1	0.8612 (2)	0.74012 (19)	1.00562 (10)	0.0127 (3)
HN1	0.938 (4)	0.835 (4)	1.0386 (19)	0.027 (7)*
C1	0.7938 (2)	0.7398 (2)	0.91829 (12)	0.0126 (3)
C2	0.7006 (2)	0.4453 (2)	0.96579 (12)	0.0127 (3)
C3	0.6389 (3)	0.2736 (2)	0.98130 (13)	0.0165 (3)
H3	0.563536	0.182216	0.934125	0.020*
C4	0.6913 (3)	0.2405 (2)	1.06823 (14)	0.0185 (3)
H4	0.650289	0.124547	1.080638	0.022*
C5	0.8032 (3)	0.3749 (2)	1.13778 (13)	0.0172 (3)
H5	0.836221	0.348582	1.196613	0.021*
C6	0.8667 (3)	0.5457 (2)	1.12210 (13)	0.0150 (3)
H6	0.943886	0.636838	1.168951	0.018*
C7	0.8134 (2)	0.5792 (2)	1.03532 (12)	0.0128 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.02600 (7)	0.02230 (6)	0.01536 (6)	0.00997 (5)	0.00446 (4)	0.00537 (4)
I2	0.03060 (7)	0.02527 (7)	0.01257 (6)	0.01186 (5)	−0.00081 (5)	0.00492 (4)
F1	0.0198 (6)	0.0426 (7)	0.0197 (6)	0.0086 (5)	−0.0015 (4)	0.0078 (5)
F2	0.0252 (6)	0.0391 (7)	0.0221 (6)	−0.0032 (5)	0.0029 (5)	0.0105 (5)
F3	0.0199 (6)	0.0372 (7)	0.0270 (7)	0.0003 (5)	−0.0064 (5)	0.0059 (5)
F4	0.0294 (6)	0.0222 (6)	0.0134 (5)	0.0085 (5)	−0.0059 (4)	0.0017 (4)
C8	0.0223 (9)	0.0171 (8)	0.0132 (8)	0.0072 (7)	0.0010 (6)	0.0024 (6)
C9	0.0202 (9)	0.0214 (9)	0.0149 (8)	0.0064 (7)	−0.0019 (6)	0.0009 (7)
C10	0.0242 (9)	0.0171 (8)	0.0126 (8)	0.0055 (7)	−0.0027 (7)	0.0023 (6)
C11	0.0232 (9)	0.0190 (9)	0.0163 (9)	0.0019 (7)	0.0018 (7)	0.0037 (7)
C12	0.0196 (9)	0.0196 (9)	0.0194 (9)	0.0020 (7)	−0.0037 (7)	0.0020 (7)
C13	0.0275 (9)	0.0147 (8)	0.0107 (8)	0.0066 (7)	−0.0029 (7)	−0.0005 (6)
S1	0.0184 (2)	0.01360 (18)	0.01265 (19)	0.00228 (15)	−0.00070 (15)	0.00408 (15)
S2	0.01404 (19)	0.01277 (18)	0.01164 (18)	0.00286 (14)	−0.00167 (14)	0.00058 (14)
N1	0.0128 (7)	0.0128 (6)	0.0110 (6)	0.0022 (5)	−0.0004 (5)	0.0018 (5)
C1	0.0124 (7)	0.0134 (7)	0.0117 (7)	0.0041 (6)	0.0017 (6)	0.0017 (6)
C2	0.0105 (7)	0.0143 (7)	0.0137 (7)	0.0044 (6)	0.0014 (6)	0.0029 (6)
C3	0.0145 (8)	0.0126 (7)	0.0209 (9)	0.0030 (6)	0.0001 (6)	0.0021 (6)
C4	0.0183 (8)	0.0150 (8)	0.0232 (9)	0.0052 (7)	0.0026 (7)	0.0073 (7)
C5	0.0158 (8)	0.0205 (8)	0.0184 (8)	0.0078 (7)	0.0020 (6)	0.0082 (7)
C6	0.0116 (7)	0.0184 (8)	0.0158 (8)	0.0055 (6)	0.0003 (6)	0.0039 (6)
C7	0.0115 (7)	0.0128 (7)	0.0142 (8)	0.0038 (6)	0.0018 (6)	0.0026 (6)

Geometric parameters (Å, º) top

I1—C8	2.0910 (19)	S2—C2	1.7452 (18)
I2—C10	2.0875 (18)	N1—HN1	0.87 (3)
F1—C9	1.343 (2)	N1—C1	1.342 (2)
F2—C11	1.337 (2)	N1—C7	1.391 (2)
F3—C12	1.341 (2)	C2—C3	1.393 (2)
F4—C13	1.346 (2)	C2—C7	1.401 (2)
C8—C9	1.390 (3)	C3—H3	0.9500
C8—C13	1.387 (3)	C3—C4	1.392 (3)
C9—C10	1.385 (3)	C4—H4	0.9500
C10—C11	1.388 (3)	C4—C5	1.401 (3)
C11—C12	1.388 (3)	C5—H5	0.9500
C12—C13	1.383 (3)	C5—C6	1.387 (3)
S1—C1	1.6799 (18)	C6—H6	0.9500
S2—C1	1.7355 (18)	C6—C7	1.393 (2)

C9—C8—I1	120.65 (14)	S1—C1—S2	122.60 (10)
C13—C8—I1	122.00 (14)	N1—C1—S1	127.05 (13)
C13—C8—C9	117.34 (18)	N1—C1—S2	110.35 (13)
F1—C9—C8	118.30 (18)	C3—C2—S2	129.26 (14)
F1—C9—C10	118.70 (17)	C3—C2—C7	120.78 (16)
C10—C9—C8	122.97 (18)	C7—C2—S2	109.95 (13)
C9—C10—I2	120.15 (14)	C2—C3—H3	121.1
C9—C10—C11	117.73 (17)	C4—C3—C2	117.77 (17)
C11—C10—I2	121.99 (14)	C4—C3—H3	121.1
F2—C11—C10	120.33 (17)	C3—C4—H4	119.4
F2—C11—C12	118.58 (18)	C3—C4—C5	121.28 (17)
C12—C11—C10	121.09 (18)	C5—C4—H4	119.4
F3—C12—C11	120.72 (18)	C4—C5—H5	119.5
F3—C12—C13	120.01 (17)	C6—C5—C4	121.03 (17)
C13—C12—C11	119.27 (18)	C6—C5—H5	119.5
F4—C13—C8	120.41 (17)	C5—C6—H6	121.1
F4—C13—C12	118.00 (17)	C5—C6—C7	117.75 (16)
C12—C13—C8	121.59 (17)	C7—C6—H6	121.1
C1—S2—C2	91.89 (8)	N1—C7—C2	111.76 (15)
C1—N1—HN1	120.5 (18)	N1—C7—C6	126.87 (16)
C1—N1—C7	116.05 (15)	C6—C7—C2	121.37 (16)
C7—N1—HN1	123.3 (18)

I1—C8—C9—F1	0.2 (2)	C13—C8—C9—F1	178.96 (17)
I1—C8—C9—C10	−178.06 (15)	C13—C8—C9—C10	0.7 (3)
I1—C8—C13—F4	−0.8 (2)	S2—C2—C3—C4	−179.54 (14)
I1—C8—C13—C12	178.95 (15)	S2—C2—C7—N1	−0.38 (18)
I2—C10—C11—F2	2.8 (3)	S2—C2—C7—C6	179.86 (13)
I2—C10—C11—C12	−176.43 (15)	C1—S2—C2—C3	−179.18 (17)
F1—C9—C10—I2	−2.9 (3)	C1—S2—C2—C7	0.60 (13)
F1—C9—C10—C11	−178.78 (18)	C1—N1—C7—C2	−0.2 (2)
F2—C11—C12—F3	1.6 (3)	C1—N1—C7—C6	179.60 (17)
F2—C11—C12—C13	−177.81 (18)	C2—S2—C1—S1	179.93 (12)
F3—C12—C13—F4	−0.9 (3)	C2—S2—C1—N1	−0.69 (13)
F3—C12—C13—C8	179.31 (17)	C2—C3—C4—C5	−0.4 (3)
C8—C9—C10—I2	175.43 (15)	C3—C2—C7—N1	179.42 (15)
C8—C9—C10—C11	−0.5 (3)	C3—C2—C7—C6	−0.3 (3)
C9—C8—C13—F4	−179.55 (16)	C3—C4—C5—C6	−0.4 (3)
C9—C8—C13—C12	0.2 (3)	C4—C5—C6—C7	0.7 (3)
C9—C10—C11—F2	178.66 (18)	C5—C6—C7—N1	179.90 (17)
C9—C10—C11—C12	−0.6 (3)	C5—C6—C7—C2	−0.4 (3)
C10—C11—C12—F3	−179.14 (18)	C7—N1—C1—S1	179.95 (13)
C10—C11—C12—C13	1.5 (3)	C7—N1—C1—S2	0.61 (19)
C11—C12—C13—F4	178.52 (17)	C7—C2—C3—C4	0.7 (3)
C11—C12—C13—C8	−1.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—HN1···S1ⁱ	0.87 (3)	2.45 (3)	3.3120 (15)	175 (2)

Symmetry code: (i) −x+2, −y+2, −z+2.

1,3-Benzothiazole-2-thiol–1,2,3,5-tetrafluoro-4,6-diiodobenzene (1/2) (MBZTH_213F4DIB) top

Crystal data top

4C₆F₄I₂·2C₇H₅NS₂	F(000) = 1768
M_r = 1941.92	D_x = 2.647 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 4.5581 (3) Å	Cell parameters from 9841 reflections
b = 34.358 (2) Å	θ = 2.4–28.8°
c = 15.6075 (10) Å	µ = 5.36 mm⁻¹
β = 94.707 (2)°	T = 100 K
V = 2436.0 (3) Å³	Prism, colourless
Z = 2	0.18 × 0.12 × 0.04 mm

Data collection top

Bruker D8 Venture Photon 2 diffractometer	11766 reflections with I > 2σ(I)
Radiation source: Incoatec IµS	R_int = 0.050
φ and ω scans	θ_max = 28.8°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2017)	h = −6→6
T_min = 0.568, T_max = 0.746	k = −46→46
56285 measured reflections	l = −21→21
12660 independent reflections

Refinement top

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)] = 0.026	w = 1/[σ²(F_o²) + (0.0071P)² + 0.5877P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.046	(Δ/σ)_max = 0.002
S = 1.09	Δρ_max = 1.01 e Å⁻³
12660 reflections	Δρ_min = −0.71 e Å⁻³
622 parameters	Absolute structure: Refined as an inversion twin
2 restraints	Absolute structure parameter: 0.454 (15)
Primary atom site location: dual

Special details top

Refinement. Refined as a 2-component inversion twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
I1	1.31057 (9)	0.37856 (2)	0.44709 (3)	0.01694 (9)
I2	0.58291 (10)	0.34353 (2)	0.11336 (3)	0.02224 (10)
I3	0.13207 (9)	0.44552 (2)	0.04395 (3)	0.01659 (9)
I4	0.84342 (11)	0.47934 (2)	0.38106 (3)	0.02660 (11)
F1	1.0269 (9)	0.38363 (11)	0.2525 (2)	0.0233 (9)
F2	0.4263 (9)	0.27169 (12)	0.2331 (3)	0.0284 (10)
F3	0.6051 (10)	0.25383 (12)	0.3971 (3)	0.0324 (10)
F4	0.9918 (10)	0.29933 (12)	0.4890 (2)	0.0276 (10)
F5	0.3945 (8)	0.44111 (11)	0.2407 (2)	0.0205 (8)
F6	1.0552 (9)	0.54664 (12)	0.2573 (3)	0.0301 (10)
F7	0.9034 (9)	0.56331 (12)	0.0915 (3)	0.0331 (10)
F8	0.4927 (9)	0.52114 (12)	0.0003 (2)	0.0247 (9)
C15	1.0262 (13)	0.34210 (19)	0.3717 (4)	0.0147 (13)
C16	0.9275 (14)	0.35093 (18)	0.2876 (4)	0.0163 (13)
C17	0.7260 (13)	0.32806 (19)	0.2383 (4)	0.0150 (13)
C18	0.6246 (14)	0.2950 (2)	0.2766 (4)	0.0181 (14)
C19	0.7144 (15)	0.2853 (2)	0.3607 (4)	0.0197 (14)
C20	0.9139 (15)	0.3087 (2)	0.4070 (4)	0.0187 (14)
C21	0.4273 (13)	0.48043 (17)	0.1192 (4)	0.0118 (12)
C22	0.5141 (14)	0.47193 (19)	0.2048 (4)	0.0160 (13)
C23	0.7212 (14)	0.49397 (19)	0.2538 (4)	0.0170 (13)
C24	0.8475 (14)	0.5248 (2)	0.2137 (5)	0.0204 (15)
C25	0.7690 (15)	0.53442 (19)	0.1293 (5)	0.0207 (15)
C26	0.5582 (14)	0.51219 (19)	0.0829 (4)	0.0164 (13)
I5	0.60231 (10)	0.58298 (2)	0.42231 (3)	0.02666 (11)
I6	−0.04120 (12)	0.67426 (2)	0.67979 (3)	0.03213 (12)
F13	0.3626 (9)	0.61104 (13)	0.5966 (2)	0.0298 (9)
F14	−0.1966 (10)	0.72120 (12)	0.5061 (3)	0.0340 (11)
F15	−0.0233 (11)	0.71370 (13)	0.3475 (3)	0.0379 (11)
F16	0.3387 (10)	0.65460 (13)	0.3104 (3)	0.0340 (10)
C33	0.3592 (15)	0.63148 (19)	0.4533 (4)	0.0215 (14)
C34	0.2700 (15)	0.63678 (19)	0.5348 (4)	0.0212 (14)
C35	0.0859 (15)	0.6674 (2)	0.5562 (4)	0.0215 (15)
C36	−0.0098 (16)	0.6922 (2)	0.4907 (5)	0.0241 (15)
C37	0.0756 (16)	0.6885 (2)	0.4086 (5)	0.0267 (16)
C38	0.2587 (16)	0.6584 (2)	0.3901 (4)	0.0241 (15)
I7	0.27675 (10)	0.60812 (2)	−0.10563 (3)	0.02281 (10)
I8	1.08854 (10)	0.74677 (2)	−0.05335 (3)	0.02152 (10)
F9	0.6582 (9)	0.68287 (11)	−0.1413 (2)	0.0239 (9)
F10	1.0852 (9)	0.71219 (12)	0.1364 (2)	0.0286 (10)
F11	0.7847 (10)	0.65341 (14)	0.2015 (2)	0.0365 (11)
F12	0.4105 (9)	0.61029 (12)	0.0985 (3)	0.0293 (9)
C27	0.5318 (14)	0.64475 (18)	−0.0249 (4)	0.0164 (13)
C28	0.6884 (14)	0.67579 (19)	−0.0565 (4)	0.0166 (13)
C29	0.8730 (13)	0.69920 (18)	−0.0044 (4)	0.0165 (13)
C30	0.9054 (15)	0.6911 (2)	0.0830 (4)	0.0219 (15)
C31	0.7507 (16)	0.6609 (2)	0.1168 (4)	0.0233 (15)
C32	0.5630 (14)	0.63862 (19)	0.0628 (4)	0.0202 (14)
S1	0.6754 (4)	0.40568 (5)	0.88863 (11)	0.0189 (3)
S2	1.0703 (4)	0.33606 (5)	0.91405 (10)	0.0186 (3)
N1	0.9694 (12)	0.36855 (16)	0.7688 (3)	0.0152 (11)
HN1	0.905 (14)	0.3871 (19)	0.732 (4)	0.007 (16)*
C1	0.8985 (13)	0.37204 (18)	0.8506 (4)	0.0151 (13)
C2	1.1602 (14)	0.33784 (19)	0.7534 (4)	0.0162 (13)
C3	1.2632 (16)	0.3281 (2)	0.6749 (4)	0.0236 (15)
H3	1.206730	0.342708	0.624462	0.028*
C4	1.4504 (15)	0.2966 (2)	0.6723 (4)	0.0261 (16)
H4	1.525655	0.289582	0.619464	0.031*
C5	1.5310 (15)	0.2748 (2)	0.7462 (5)	0.0262 (16)
H5	1.657929	0.253028	0.742875	0.031*
C6	1.4270 (15)	0.28477 (19)	0.8243 (4)	0.0201 (14)
H6	1.483893	0.270321	0.874871	0.024*
C7	1.2378 (14)	0.31638 (19)	0.8270 (4)	0.0168 (13)
S3	0.7312 (4)	0.42496 (5)	0.60016 (10)	0.0190 (3)
S4	0.3357 (4)	0.49495 (5)	0.57647 (10)	0.0180 (3)
N2	0.4180 (12)	0.45945 (16)	0.7190 (3)	0.0164 (12)
HN2	0.497 (15)	0.449 (2)	0.764 (3)	0.03 (2)*
C8	0.4996 (14)	0.45745 (19)	0.6383 (4)	0.0162 (13)
C9	0.2219 (14)	0.48927 (19)	0.7357 (4)	0.0174 (13)
C10	0.1004 (14)	0.4970 (2)	0.8131 (4)	0.0190 (14)
H10	0.149370	0.481541	0.862699	0.023*
C11	−0.0915 (15)	0.5276 (2)	0.8154 (4)	0.0221 (15)
H11	−0.179266	0.533075	0.867172	0.027*
C12	−0.1615 (15)	0.5510 (2)	0.7427 (4)	0.0208 (14)
H12	−0.295108	0.572001	0.746348	0.025*
C13	−0.0391 (14)	0.5439 (2)	0.6659 (4)	0.0220 (15)
H13	−0.083511	0.560008	0.617145	0.026*
C14	0.1515 (13)	0.51230 (19)	0.6627 (4)	0.0158 (13)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.0177 (2)	0.0159 (2)	0.01700 (19)	0.00011 (16)	0.00007 (16)	−0.00234 (17)
I2	0.0263 (2)	0.0245 (2)	0.0153 (2)	0.00547 (19)	−0.00254 (18)	−0.00115 (18)
I3	0.0171 (2)	0.0170 (2)	0.01558 (19)	0.00146 (16)	0.00089 (16)	−0.00224 (17)
I4	0.0313 (3)	0.0303 (3)	0.0169 (2)	0.0123 (2)	−0.00624 (19)	−0.00536 (19)
F1	0.032 (2)	0.019 (2)	0.0194 (19)	−0.0084 (17)	0.0019 (17)	0.0046 (17)
F2	0.028 (2)	0.029 (2)	0.027 (2)	−0.0075 (18)	−0.0056 (18)	−0.0054 (19)
F3	0.041 (3)	0.023 (2)	0.033 (2)	−0.0147 (19)	−0.001 (2)	0.0100 (19)
F4	0.040 (3)	0.025 (2)	0.0168 (19)	−0.0053 (19)	−0.0029 (18)	0.0056 (17)
F5	0.029 (2)	0.016 (2)	0.0167 (18)	−0.0053 (17)	0.0061 (16)	0.0037 (16)
F6	0.019 (2)	0.029 (2)	0.042 (3)	−0.0079 (18)	−0.0024 (19)	−0.010 (2)
F7	0.032 (2)	0.024 (2)	0.044 (3)	−0.0084 (19)	0.011 (2)	0.010 (2)
F8	0.029 (2)	0.028 (2)	0.0170 (19)	−0.0002 (18)	0.0002 (17)	0.0100 (17)
C15	0.010 (3)	0.016 (3)	0.019 (3)	0.000 (2)	0.002 (2)	−0.001 (3)
C16	0.017 (3)	0.013 (3)	0.020 (3)	0.001 (2)	0.005 (3)	0.003 (3)
C17	0.013 (3)	0.021 (4)	0.011 (3)	0.002 (3)	0.000 (2)	−0.001 (3)
C18	0.016 (3)	0.019 (4)	0.018 (3)	−0.002 (3)	−0.001 (3)	−0.002 (3)
C19	0.021 (4)	0.017 (4)	0.021 (3)	−0.004 (3)	0.004 (3)	−0.001 (3)
C20	0.024 (4)	0.017 (4)	0.014 (3)	0.004 (3)	0.001 (3)	0.001 (3)
C21	0.017 (3)	0.009 (3)	0.010 (3)	0.001 (2)	0.003 (2)	−0.001 (2)
C22	0.018 (3)	0.015 (3)	0.016 (3)	0.001 (3)	0.007 (3)	0.001 (3)
C23	0.017 (3)	0.016 (3)	0.016 (3)	0.004 (3)	−0.003 (3)	−0.002 (3)
C24	0.012 (3)	0.021 (4)	0.028 (4)	0.000 (3)	0.000 (3)	−0.008 (3)
C25	0.018 (3)	0.009 (3)	0.035 (4)	−0.002 (3)	0.007 (3)	0.006 (3)
C26	0.014 (3)	0.017 (3)	0.018 (3)	−0.001 (3)	0.004 (3)	0.002 (3)
I5	0.0251 (2)	0.0252 (3)	0.0291 (2)	0.00486 (19)	−0.00180 (19)	−0.0083 (2)
I6	0.0376 (3)	0.0383 (3)	0.0218 (2)	0.0001 (2)	0.0099 (2)	−0.0023 (2)
F13	0.037 (2)	0.029 (2)	0.024 (2)	0.002 (2)	0.0010 (19)	0.0053 (19)
F14	0.034 (3)	0.031 (3)	0.038 (2)	0.014 (2)	0.012 (2)	0.000 (2)
F15	0.047 (3)	0.033 (3)	0.032 (2)	0.005 (2)	−0.002 (2)	0.019 (2)
F16	0.036 (3)	0.045 (3)	0.021 (2)	0.009 (2)	0.0073 (19)	0.0024 (19)
C33	0.022 (4)	0.016 (3)	0.027 (4)	0.001 (3)	0.003 (3)	−0.004 (3)
C34	0.024 (4)	0.019 (4)	0.021 (3)	−0.005 (3)	−0.001 (3)	0.003 (3)
C35	0.024 (4)	0.021 (4)	0.021 (3)	−0.002 (3)	0.011 (3)	−0.003 (3)
C36	0.021 (4)	0.020 (4)	0.031 (4)	−0.001 (3)	0.002 (3)	−0.002 (3)
C37	0.023 (4)	0.030 (4)	0.028 (4)	0.001 (3)	0.006 (3)	0.008 (3)
C38	0.027 (4)	0.030 (4)	0.016 (3)	−0.001 (3)	0.006 (3)	0.002 (3)
I7	0.0204 (2)	0.0188 (2)	0.0290 (2)	−0.00085 (18)	−0.00007 (19)	−0.00546 (19)
I8	0.0220 (2)	0.0161 (2)	0.0263 (2)	−0.00127 (17)	0.00103 (18)	0.00192 (18)
F9	0.029 (2)	0.025 (2)	0.0171 (19)	−0.0009 (17)	−0.0005 (17)	−0.0004 (16)
F10	0.028 (2)	0.036 (3)	0.021 (2)	−0.0123 (19)	0.0001 (18)	−0.0051 (18)
F11	0.039 (3)	0.052 (3)	0.018 (2)	−0.013 (2)	0.0041 (19)	0.004 (2)
F12	0.026 (2)	0.030 (2)	0.034 (2)	−0.0084 (19)	0.0099 (19)	0.006 (2)
C27	0.015 (3)	0.009 (3)	0.025 (3)	−0.001 (2)	−0.002 (3)	−0.005 (3)
C28	0.018 (3)	0.016 (3)	0.015 (3)	0.003 (3)	0.001 (3)	0.002 (3)
C29	0.010 (3)	0.012 (3)	0.027 (3)	−0.001 (2)	0.004 (3)	−0.003 (3)
C30	0.018 (3)	0.027 (4)	0.021 (3)	−0.002 (3)	0.001 (3)	−0.005 (3)
C31	0.025 (4)	0.030 (4)	0.015 (3)	0.002 (3)	0.002 (3)	0.000 (3)
C32	0.017 (3)	0.016 (3)	0.030 (4)	0.000 (3)	0.010 (3)	0.000 (3)
S1	0.0189 (8)	0.0203 (9)	0.0175 (8)	0.0005 (7)	0.0009 (7)	−0.0035 (7)
S2	0.0224 (8)	0.0197 (9)	0.0134 (7)	−0.0011 (7)	−0.0004 (6)	0.0024 (6)
N1	0.022 (3)	0.014 (3)	0.010 (2)	0.000 (2)	0.000 (2)	0.002 (2)
C1	0.013 (3)	0.016 (3)	0.016 (3)	−0.004 (2)	0.000 (2)	−0.001 (3)
C2	0.015 (3)	0.017 (3)	0.016 (3)	−0.004 (3)	−0.002 (3)	−0.003 (3)
C3	0.024 (4)	0.030 (4)	0.016 (3)	0.001 (3)	0.002 (3)	0.001 (3)
C4	0.019 (4)	0.035 (4)	0.023 (4)	0.003 (3)	−0.003 (3)	−0.008 (3)
C5	0.017 (4)	0.027 (4)	0.033 (4)	0.004 (3)	−0.004 (3)	−0.008 (3)
C6	0.021 (4)	0.019 (4)	0.020 (3)	0.000 (3)	−0.003 (3)	−0.002 (3)
C7	0.016 (3)	0.018 (3)	0.015 (3)	−0.002 (3)	−0.004 (3)	−0.004 (3)
S3	0.0190 (8)	0.0206 (9)	0.0172 (8)	−0.0007 (7)	0.0001 (7)	−0.0018 (7)
S4	0.0191 (8)	0.0217 (9)	0.0129 (7)	−0.0017 (7)	0.0002 (6)	0.0016 (6)
N2	0.013 (3)	0.020 (3)	0.015 (3)	−0.001 (2)	−0.002 (2)	0.003 (2)
C8	0.017 (3)	0.018 (3)	0.013 (3)	−0.007 (3)	−0.001 (3)	−0.001 (2)
C9	0.017 (3)	0.019 (3)	0.015 (3)	−0.005 (3)	−0.004 (3)	−0.002 (3)
C10	0.021 (3)	0.022 (4)	0.014 (3)	−0.006 (3)	0.003 (3)	0.001 (3)
C11	0.026 (4)	0.025 (4)	0.016 (3)	−0.006 (3)	0.007 (3)	−0.008 (3)
C12	0.018 (3)	0.019 (4)	0.025 (4)	0.000 (3)	0.003 (3)	−0.006 (3)
C13	0.017 (3)	0.022 (4)	0.026 (4)	−0.003 (3)	−0.004 (3)	0.003 (3)
C14	0.011 (3)	0.020 (3)	0.015 (3)	−0.004 (3)	−0.002 (3)	−0.003 (3)

Geometric parameters (Å, º) top

I1—C15	2.094 (6)	F11—C31	1.344 (7)
I2—C17	2.075 (6)	F12—C32	1.343 (7)
I3—C21	2.090 (6)	C27—C28	1.396 (9)
I4—C23	2.080 (6)	C27—C32	1.381 (9)
F1—C16	1.345 (7)	C28—C29	1.379 (9)
F2—C18	1.349 (8)	C29—C30	1.387 (9)
F3—C19	1.336 (7)	C30—C31	1.383 (9)
F4—C20	1.338 (7)	C31—C32	1.382 (10)
F5—C22	1.335 (7)	S1—C1	1.679 (6)
F6—C24	1.348 (8)	S2—C1	1.730 (7)
F7—C25	1.330 (7)	S2—C7	1.748 (7)
F8—C26	1.336 (7)	N1—HN1	0.89 (6)
C15—C16	1.386 (9)	N1—C1	1.347 (7)
C15—C20	1.389 (9)	N1—C2	1.401 (8)
C16—C17	1.391 (9)	C2—C3	1.389 (9)
C17—C18	1.381 (9)	C2—C7	1.385 (9)
C18—C19	1.383 (9)	C3—H3	0.9500
C19—C20	1.373 (10)	C3—C4	1.382 (10)
C21—C22	1.393 (8)	C4—H4	0.9500
C21—C26	1.387 (8)	C4—C5	1.398 (10)
C22—C23	1.389 (9)	C5—H5	0.9500
C23—C24	1.380 (10)	C5—C6	1.387 (9)
C24—C25	1.377 (10)	C6—H6	0.9500
C25—C26	1.384 (9)	C6—C7	1.390 (9)
I5—C33	2.080 (6)	S3—C8	1.679 (7)
I6—C35	2.073 (6)	S4—C8	1.741 (7)
F13—C34	1.351 (8)	S4—C14	1.748 (6)
F14—C36	1.346 (8)	N2—HN2	0.85 (3)
F15—C37	1.339 (8)	N2—C8	1.343 (8)
F16—C38	1.331 (7)	N2—C9	1.398 (8)
C33—C34	1.380 (9)	C9—C10	1.396 (9)
C33—C38	1.400 (10)	C9—C14	1.403 (9)
C34—C35	1.402 (9)	C10—H10	0.9500
C35—C36	1.373 (10)	C10—C11	1.369 (10)
C36—C37	1.375 (10)	C11—H11	0.9500
C37—C38	1.375 (10)	C11—C12	1.405 (9)
I7—C27	2.069 (6)	C12—H12	0.9500
I8—C29	2.085 (6)	C12—C13	1.384 (9)
F9—C28	1.342 (7)	C13—H13	0.9500
F10—C30	1.334 (8)	C13—C14	1.394 (9)

C16—C15—I1	122.6 (5)	C28—C29—C30	118.2 (6)
C16—C15—C20	117.1 (6)	C30—C29—I8	120.1 (5)
C20—C15—I1	120.2 (5)	F10—C30—C29	121.1 (6)
F1—C16—C15	118.3 (6)	F10—C30—C31	118.4 (6)
F1—C16—C17	118.4 (6)	C31—C30—C29	120.6 (6)
C15—C16—C17	123.2 (6)	F11—C31—C30	119.9 (6)
C16—C17—I2	121.1 (5)	F11—C31—C32	120.5 (6)
C18—C17—I2	121.8 (5)	C32—C31—C30	119.6 (6)
C18—C17—C16	117.1 (6)	F12—C32—C27	120.5 (6)
F2—C18—C17	120.3 (6)	F12—C32—C31	117.7 (6)
F2—C18—C19	118.0 (6)	C27—C32—C31	121.8 (6)
C17—C18—C19	121.7 (6)	C1—S2—C7	92.2 (3)
F3—C19—C18	120.4 (6)	C1—N1—HN1	117 (4)
F3—C19—C20	120.2 (6)	C1—N1—C2	115.5 (5)
C20—C19—C18	119.3 (6)	C2—N1—HN1	127 (4)
F4—C20—C15	120.0 (6)	S1—C1—S2	123.3 (4)
F4—C20—C19	118.3 (6)	N1—C1—S1	126.5 (5)
C19—C20—C15	121.6 (6)	N1—C1—S2	110.2 (5)
C22—C21—I3	122.5 (5)	C3—C2—N1	126.3 (6)
C26—C21—I3	120.1 (4)	C7—C2—N1	112.2 (6)
C26—C21—C22	117.3 (6)	C7—C2—C3	121.5 (6)
F5—C22—C21	118.4 (6)	C2—C3—H3	121.1
F5—C22—C23	118.9 (6)	C4—C3—C2	117.9 (6)
C23—C22—C21	122.7 (6)	C4—C3—H3	121.1
C22—C23—I4	120.7 (5)	C3—C4—H4	119.4
C24—C23—I4	122.0 (5)	C3—C4—C5	121.1 (7)
C24—C23—C22	117.3 (6)	C5—C4—H4	119.4
F6—C24—C23	120.0 (6)	C4—C5—H5	119.8
F6—C24—C25	117.8 (6)	C6—C5—C4	120.5 (7)
C25—C24—C23	122.2 (6)	C6—C5—H5	119.8
F7—C25—C24	120.7 (6)	C5—C6—H6	120.8
F7—C25—C26	120.3 (6)	C5—C6—C7	118.5 (6)
C24—C25—C26	118.9 (6)	C7—C6—H6	120.8
F8—C26—C21	120.4 (6)	C2—C7—S2	109.9 (5)
F8—C26—C25	117.9 (6)	C2—C7—C6	120.5 (6)
C25—C26—C21	121.6 (6)	C6—C7—S2	129.6 (5)
C34—C33—I5	121.5 (5)	C8—S4—C14	92.1 (3)
C34—C33—C38	117.3 (6)	C8—N2—HN2	129 (5)
C38—C33—I5	121.0 (5)	C8—N2—C9	116.3 (6)
F13—C34—C33	118.3 (6)	C9—N2—HN2	113 (5)
F13—C34—C35	118.6 (6)	S3—C8—S4	123.3 (4)
C33—C34—C35	123.1 (6)	N2—C8—S3	126.7 (5)
C34—C35—I6	121.7 (5)	N2—C8—S4	110.0 (5)
C36—C35—I6	121.7 (5)	N2—C9—C14	111.7 (6)
C36—C35—C34	116.6 (6)	C10—C9—N2	127.3 (6)
F14—C36—C35	119.6 (6)	C10—C9—C14	121.0 (6)
F14—C36—C37	117.8 (6)	C9—C10—H10	121.0
C35—C36—C37	122.6 (7)	C11—C10—C9	117.9 (6)
F15—C37—C36	120.0 (6)	C11—C10—H10	121.0
F15—C37—C38	120.8 (6)	C10—C11—H11	119.3
C38—C37—C36	119.2 (7)	C10—C11—C12	121.4 (6)
F16—C38—C33	119.7 (6)	C12—C11—H11	119.3
F16—C38—C37	119.1 (6)	C11—C12—H12	119.4
C37—C38—C33	121.2 (6)	C13—C12—C11	121.2 (6)
C28—C27—I7	121.9 (5)	C13—C12—H12	119.4
C32—C27—I7	121.2 (5)	C12—C13—H13	121.1
C32—C27—C28	116.9 (6)	C12—C13—C14	117.7 (6)
F9—C28—C27	118.2 (6)	C14—C13—H13	121.1
F9—C28—C29	118.9 (6)	C9—C14—S4	109.9 (5)
C29—C28—C27	122.9 (6)	C13—C14—S4	129.3 (5)
C28—C29—I8	121.6 (5)	C13—C14—C9	120.7 (6)

I1—C15—C16—F1	2.2 (8)	C35—C36—C37—C38	1.5 (11)
I1—C15—C16—C17	−176.3 (5)	C36—C37—C38—F16	179.3 (6)
I1—C15—C20—F4	−1.3 (8)	C36—C37—C38—C33	0.0 (11)
I1—C15—C20—C19	176.4 (5)	C38—C33—C34—F13	179.5 (6)
I2—C17—C18—F2	−0.2 (9)	C38—C33—C34—C35	0.1 (10)
I2—C17—C18—C19	−178.3 (5)	I7—C27—C28—F9	3.5 (8)
I3—C21—C22—F5	−2.7 (8)	I7—C27—C28—C29	−176.2 (5)
I3—C21—C22—C23	176.7 (5)	I7—C27—C32—F12	−4.9 (9)
I3—C21—C26—F8	1.3 (8)	I7—C27—C32—C31	174.8 (5)
I3—C21—C26—C25	−175.7 (5)	I8—C29—C30—F10	−3.5 (9)
I4—C23—C24—F6	−0.5 (9)	I8—C29—C30—C31	176.4 (5)
I4—C23—C24—C25	179.5 (5)	F9—C28—C29—I8	3.1 (8)
F1—C16—C17—I2	0.4 (8)	F9—C28—C29—C30	−179.0 (6)
F1—C16—C17—C18	−179.0 (6)	F10—C30—C31—F11	−0.2 (10)
F2—C18—C19—F3	−0.4 (10)	F10—C30—C31—C32	−179.9 (6)
F2—C18—C19—C20	−179.4 (6)	F11—C31—C32—F12	2.2 (10)
F3—C19—C20—F4	−0.8 (10)	F11—C31—C32—C27	−177.6 (6)
F3—C19—C20—C15	−178.5 (6)	C27—C28—C29—I8	−177.3 (5)
F5—C22—C23—I4	−0.1 (8)	C27—C28—C29—C30	0.6 (10)
F5—C22—C23—C24	177.8 (6)	C28—C27—C32—F12	177.4 (6)
F6—C24—C25—F7	2.8 (10)	C28—C27—C32—C31	−2.9 (10)
F6—C24—C25—C26	179.4 (6)	C28—C29—C30—F10	178.6 (6)
F7—C25—C26—F8	−1.0 (10)	C28—C29—C30—C31	−1.5 (10)
F7—C25—C26—C21	176.0 (6)	C29—C30—C31—F11	179.9 (6)
C15—C16—C17—I2	179.0 (5)	C29—C30—C31—C32	0.2 (10)
C15—C16—C17—C18	−0.4 (10)	C30—C31—C32—F12	−178.1 (6)
C16—C15—C20—F4	−177.5 (6)	C30—C31—C32—C27	2.1 (10)
C16—C15—C20—C19	0.2 (10)	C32—C27—C28—F9	−178.8 (6)
C16—C17—C18—F2	179.2 (6)	C32—C27—C28—C29	1.5 (10)
C16—C17—C18—C19	1.2 (10)	N1—C2—C3—C4	−179.8 (6)
C17—C18—C19—F3	177.7 (6)	N1—C2—C7—S2	−0.7 (7)
C17—C18—C19—C20	−1.3 (11)	N1—C2—C7—C6	−179.7 (6)
C18—C19—C20—F4	178.3 (6)	C1—S2—C7—C2	0.5 (5)
C18—C19—C20—C15	0.6 (10)	C1—S2—C7—C6	179.4 (7)
C20—C15—C16—F1	178.3 (5)	C1—N1—C2—C3	179.5 (6)
C20—C15—C16—C17	−0.2 (10)	C1—N1—C2—C7	0.6 (8)
C21—C22—C23—I4	−179.5 (5)	C2—N1—C1—S1	−179.8 (5)
C21—C22—C23—C24	−1.5 (10)	C2—N1—C1—S2	−0.2 (7)
C22—C21—C26—F8	177.6 (6)	C2—C3—C4—C5	0.8 (11)
C22—C21—C26—C25	0.7 (9)	C3—C2—C7—S2	−179.7 (5)
C22—C23—C24—F6	−178.3 (6)	C3—C2—C7—C6	1.3 (10)
C22—C23—C24—C25	1.6 (10)	C3—C4—C5—C6	−0.8 (11)
C23—C24—C25—F7	−177.2 (6)	C4—C5—C6—C7	1.1 (10)
C23—C24—C25—C26	−0.6 (10)	C5—C6—C7—S2	179.9 (5)
C24—C25—C26—F8	−177.7 (6)	C5—C6—C7—C2	−1.3 (10)
C24—C25—C26—C21	−0.6 (10)	C7—S2—C1—S1	179.5 (4)
C26—C21—C22—F5	−178.9 (5)	C7—S2—C1—N1	−0.2 (5)
C26—C21—C22—C23	0.4 (9)	C7—C2—C3—C4	−1.0 (10)
I5—C33—C34—F13	4.8 (9)	N2—C9—C10—C11	−179.2 (6)
I5—C33—C34—C35	−174.6 (5)	N2—C9—C14—S4	0.3 (7)
I5—C33—C38—F16	−5.4 (9)	N2—C9—C14—C13	−179.4 (6)
I5—C33—C38—C37	174.0 (6)	C8—S4—C14—C9	0.4 (5)
I6—C35—C36—F14	−1.7 (10)	C8—S4—C14—C13	−180.0 (6)
I6—C35—C36—C37	178.9 (6)	C8—N2—C9—C10	178.6 (6)
F13—C34—C35—I6	0.9 (9)	C8—N2—C9—C14	−1.1 (8)
F13—C34—C35—C36	−178.2 (6)	C9—N2—C8—S3	179.9 (5)
F14—C36—C37—F15	1.1 (10)	C9—N2—C8—S4	1.4 (7)
F14—C36—C37—C38	−177.9 (7)	C9—C10—C11—C12	−1.0 (10)
F15—C37—C38—F16	0.4 (11)	C10—C9—C14—S4	−179.5 (5)
F15—C37—C38—C33	−179.0 (7)	C10—C9—C14—C13	0.8 (10)
C33—C34—C35—I6	−179.8 (5)	C10—C11—C12—C13	0.2 (11)
C33—C34—C35—C36	1.2 (10)	C11—C12—C13—C14	1.2 (10)
C34—C33—C38—F16	179.9 (6)	C12—C13—C14—S4	178.7 (5)
C34—C33—C38—C37	−0.8 (11)	C12—C13—C14—C9	−1.7 (10)
C34—C35—C36—F14	177.3 (6)	C14—S4—C8—S3	−179.6 (4)
C34—C35—C36—C37	−2.0 (11)	C14—S4—C8—N2	−1.0 (5)
C35—C36—C37—F15	−179.5 (7)	C14—C9—C10—C11	0.5 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—HN1···S3	0.89 (6)	2.51 (6)	3.376 (6)	165 (5)
C3—H3···I1	0.95	3.10	3.976 (7)	154
N2—HN2···S1	0.85 (3)	2.52 (3)	3.360 (6)	169 (7)
C10—H10···I3ⁱ	0.95	3.09	4.006 (6)	161

Symmetry code: (i) x, y, z+1.

1,3-Benzothiazole-2-thiol–1,2,4,5-tetrafluoro-3,6-diiodobenzene (2/1) (2MBZTH_14F4DIB) top

Crystal data top

C₆F₄I₂·2C₇H₅NS₂	F(000) = 700
M_r = 736.34	D_x = 2.111 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 5.5057 (2) Å	Cell parameters from 9937 reflections
b = 15.6087 (7) Å	θ = 2.6–30.1°
c = 13.5194 (6) Å	µ = 3.12 mm⁻¹
β = 94.259 (2)°	T = 100 K
V = 1158.61 (8) Å³	Needle, colourless
Z = 2	0.17 × 0.09 × 0.04 mm

Data collection top

Bruker D8 Venture Photon 2 diffractometer	2811 reflections with I > 2σ(I)
Radiation source: Incoatec IµS	R_int = 0.049
φ and ω scans	θ_max = 30.1°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2017)	h = −7→7
T_min = 0.559, T_max = 0.746	k = −22→21
22270 measured reflections	l = −18→19
3402 independent reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.027	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.057	w = 1/[σ²(F_o²) + (0.0092P)² + 1.689P] where P = (F_o² + 2F_c²)/3
S = 1.15	(Δ/σ)_max = 0.001
3402 reflections	Δρ_max = 0.90 e Å⁻³
149 parameters	Δρ_min = −0.78 e Å⁻³
0 restraints

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
I1	0.09620 (3)	0.50667 (2)	0.18841 (2)	0.01843 (6)
F1	0.4987 (3)	0.36936 (10)	0.13226 (14)	0.0285 (4)
F2	0.8063 (3)	0.36478 (10)	−0.00971 (13)	0.0267 (4)
C8	0.3371 (5)	0.50280 (17)	0.0761 (2)	0.0179 (5)
C9	0.4956 (5)	0.43488 (17)	0.0673 (2)	0.0210 (6)
C10	0.6546 (5)	0.43202 (17)	−0.0070 (2)	0.0190 (5)
S1	−0.29400 (12)	0.50758 (4)	0.36239 (5)	0.01927 (14)
S2	0.07419 (13)	0.64355 (4)	0.42496 (5)	0.02067 (15)
N1	−0.2698 (4)	0.60239 (14)	0.52996 (18)	0.0175 (5)
HN1	−0.379 (6)	0.577 (2)	0.548 (3)	0.024 (9)*
C1	−0.1812 (5)	0.58112 (16)	0.4433 (2)	0.0166 (5)
C2	−0.1450 (5)	0.66593 (16)	0.5855 (2)	0.0173 (5)
C3	−0.2004 (5)	0.69814 (17)	0.6767 (2)	0.0225 (6)
H3	−0.337581	0.678027	0.708502	0.027*
C4	−0.0491 (6)	0.76050 (19)	0.7197 (2)	0.0271 (7)
H4	−0.083090	0.783531	0.782261	0.032*
C5	0.1516 (6)	0.79028 (19)	0.6737 (2)	0.0269 (7)
H5	0.253410	0.832708	0.705534	0.032*
C6	0.2060 (5)	0.75900 (17)	0.5816 (2)	0.0237 (6)
H6	0.342177	0.779762	0.549629	0.028*
C7	0.0542 (5)	0.69629 (16)	0.5379 (2)	0.0178 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.01632 (9)	0.02275 (9)	0.01671 (10)	0.00025 (7)	0.00446 (6)	−0.00296 (6)
F1	0.0349 (10)	0.0250 (8)	0.0273 (10)	0.0077 (7)	0.0135 (8)	0.0069 (7)
F2	0.0284 (9)	0.0247 (8)	0.0283 (10)	0.0099 (7)	0.0107 (8)	0.0003 (7)
C8	0.0152 (12)	0.0226 (13)	0.0162 (14)	−0.0007 (10)	0.0035 (10)	−0.0063 (10)
C9	0.0216 (14)	0.0217 (13)	0.0200 (15)	−0.0003 (11)	0.0031 (12)	−0.0003 (10)
C10	0.0169 (12)	0.0196 (12)	0.0207 (15)	0.0022 (10)	0.0019 (11)	−0.0047 (10)
S1	0.0194 (3)	0.0228 (3)	0.0161 (3)	−0.0054 (3)	0.0047 (3)	−0.0013 (2)
S2	0.0195 (3)	0.0236 (3)	0.0198 (4)	−0.0062 (3)	0.0071 (3)	−0.0005 (3)
N1	0.0170 (11)	0.0165 (10)	0.0196 (13)	−0.0033 (9)	0.0057 (9)	0.0011 (9)
C1	0.0154 (12)	0.0176 (12)	0.0170 (14)	−0.0002 (10)	0.0030 (10)	0.0036 (9)
C2	0.0189 (13)	0.0148 (11)	0.0184 (14)	−0.0022 (10)	0.0016 (11)	0.0020 (9)
C3	0.0227 (14)	0.0226 (13)	0.0230 (16)	0.0016 (11)	0.0061 (12)	0.0009 (11)
C4	0.0322 (16)	0.0254 (14)	0.0238 (17)	0.0003 (12)	0.0036 (13)	−0.0066 (12)
C5	0.0273 (15)	0.0221 (14)	0.0307 (18)	−0.0041 (12)	−0.0022 (13)	−0.0029 (12)
C6	0.0232 (14)	0.0194 (13)	0.0286 (17)	−0.0051 (11)	0.0023 (12)	0.0013 (11)
C7	0.0173 (12)	0.0170 (12)	0.0193 (15)	−0.0007 (10)	0.0027 (11)	0.0026 (10)

Geometric parameters (Å, º) top

I1—C8	2.090 (3)	N1—C2	1.394 (4)
F1—C9	1.348 (3)	C2—C3	1.386 (4)
F2—C10	1.344 (3)	C2—C7	1.395 (4)
C8—C9	1.384 (4)	C3—H3	0.9500
C8—C10ⁱ	1.385 (4)	C3—C4	1.381 (4)
C9—C10	1.381 (4)	C4—H4	0.9500
S1—C1	1.673 (3)	C4—C5	1.388 (4)
S2—C1	1.743 (3)	C5—H5	0.9500
S2—C7	1.746 (3)	C5—C6	1.390 (4)
N1—HN1	0.78 (3)	C6—H6	0.9500
N1—C1	1.344 (3)	C6—C7	1.390 (4)

C9—C8—I1	121.6 (2)	C3—C2—N1	127.2 (2)
C9—C8—C10ⁱ	116.8 (2)	C3—C2—C7	121.3 (3)
C10ⁱ—C8—I1	121.59 (19)	C2—C3—H3	121.2
F1—C9—C8	120.2 (2)	C4—C3—C2	117.7 (3)
F1—C9—C10	118.1 (2)	C4—C3—H3	121.2
C10—C9—C8	121.7 (3)	C3—C4—H4	119.3
F2—C10—C8ⁱ	120.2 (2)	C3—C4—C5	121.5 (3)
F2—C10—C9	118.3 (2)	C5—C4—H4	119.3
C9—C10—C8ⁱ	121.4 (2)	C4—C5—H5	119.5
C1—S2—C7	92.03 (13)	C4—C5—C6	121.0 (3)
C1—N1—HN1	119 (3)	C6—C5—H5	119.5
C1—N1—C2	116.7 (2)	C5—C6—H6	121.1
C2—N1—HN1	124 (3)	C7—C6—C5	117.7 (3)
S1—C1—S2	123.72 (16)	C7—C6—H6	121.1
N1—C1—S1	126.7 (2)	C2—C7—S2	110.2 (2)
N1—C1—S2	109.5 (2)	C6—C7—S2	128.9 (2)
N1—C2—C7	111.5 (2)	C6—C7—C2	120.8 (3)

I1—C8—C9—F1	−0.5 (4)	C1—N1—C2—C7	0.3 (3)
I1—C8—C9—C10	179.8 (2)	C2—N1—C1—S1	−180.0 (2)
F1—C9—C10—F2	−0.9 (4)	C2—N1—C1—S2	−0.7 (3)
F1—C9—C10—C8ⁱ	−179.6 (3)	C2—C3—C4—C5	0.1 (5)
C8—C9—C10—F2	178.7 (3)	C3—C2—C7—S2	−179.8 (2)
C8—C9—C10—C8ⁱ	0.0 (5)	C3—C2—C7—C6	1.1 (4)
C10ⁱ—C8—C9—F1	179.6 (3)	C3—C4—C5—C6	0.8 (5)
C10ⁱ—C8—C9—C10	0.0 (5)	C4—C5—C6—C7	−0.7 (5)
N1—C2—C3—C4	179.0 (3)	C5—C6—C7—S2	−179.2 (2)
N1—C2—C7—S2	0.2 (3)	C5—C6—C7—C2	−0.2 (4)
N1—C2—C7—C6	−178.9 (3)	C7—S2—C1—S1	180.00 (19)
C1—S2—C7—C2	−0.5 (2)	C7—S2—C1—N1	0.7 (2)
C1—S2—C7—C6	178.5 (3)	C7—C2—C3—C4	−1.0 (4)
C1—N1—C2—C3	−179.7 (3)

Symmetry code: (i) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—HN1···S1ⁱⁱ	0.78 (3)	2.60 (3)	3.369 (2)	170 (3)
C3—H3···F1ⁱⁱⁱ	0.95	2.50	3.333 (3)	146
C6—H6···F2^iv	0.95	2.44	3.357 (3)	162

Symmetry codes: (ii) −x−1, −y+1, −z+1; (iii) −x, −y+1, −z+1; (iv) −x+3/2, y+1/2, −z+1/2.

1,3-Benzothiazole-2-thiol–1,3,5-trifluoro-2,4,6-triiodobenzene (1/1) (MBZTH_135F3I3B) top

Crystal data top

C₆F₃I₃·C₇H₅NS₂	F(000) = 1232
M_r = 677.00	D_x = 2.681 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 15.2665 (6) Å	Cell parameters from 9894 reflections
b = 4.7380 (2) Å	θ = 3.1–28.4°
c = 23.2215 (10) Å	µ = 5.86 mm⁻¹
β = 93.139 (2)°	T = 100 K
V = 1677.15 (12) Å³	Plate, colourless
Z = 4	0.16 × 0.08 × 0.05 mm

Data collection top

Bruker D8 Venture Photon 2 diffractometer	3611 reflections with I > 2σ(I)
Radiation source: Incoatec IµS	R_int = 0.057
φ and ω scans	θ_max = 28.4°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2017)	h = −19→20
T_min = 0.610, T_max = 0.746	k = −6→6
35222 measured reflections	l = −30→31
4212 independent reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.024	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.052	w = 1/[σ²(F_o²) + 4.0997P] where P = (F_o² + 2F_c²)/3
S = 1.18	(Δ/σ)_max = 0.003
4212 reflections	Δρ_max = 0.67 e Å⁻³
203 parameters	Δρ_min = −0.73 e Å⁻³
1 restraint

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
I1	0.70161 (2)	0.58105 (5)	0.55847 (2)	0.01897 (6)
I2	0.68104 (2)	−0.18871 (6)	0.76567 (2)	0.02456 (7)
I3	0.37648 (2)	−0.11384 (6)	0.58903 (2)	0.02243 (6)
F1	0.75133 (13)	0.2505 (5)	0.67513 (9)	0.0224 (5)
F2	0.49679 (14)	−0.2816 (5)	0.70076 (9)	0.0247 (5)
F3	0.51145 (13)	0.3138 (5)	0.54048 (9)	0.0224 (5)
C8	0.6317 (2)	0.2972 (7)	0.60769 (15)	0.0161 (7)
C9	0.6683 (2)	0.1805 (8)	0.65793 (15)	0.0168 (7)
C10	0.6242 (2)	−0.0129 (8)	0.69039 (15)	0.0170 (7)
C11	0.5404 (2)	−0.0910 (8)	0.67047 (15)	0.0195 (7)
C12	0.5008 (2)	0.0172 (8)	0.62016 (15)	0.0170 (7)
C13	0.5477 (2)	0.2102 (8)	0.58980 (15)	0.0177 (7)
S1	0.85079 (6)	1.0132 (2)	0.49475 (4)	0.02217 (19)
S2	0.81182 (6)	0.6044 (2)	0.39819 (4)	0.02095 (19)
N1	0.9677 (2)	0.7071 (7)	0.43672 (13)	0.0205 (6)
HN1	1.011 (2)	0.777 (10)	0.4571 (18)	0.040 (14)*
C1	0.8842 (2)	0.7835 (8)	0.44595 (15)	0.0185 (7)
C2	0.9777 (2)	0.5076 (8)	0.39362 (16)	0.0203 (7)
C3	1.0556 (3)	0.3935 (9)	0.37636 (18)	0.0278 (9)
H3	1.110354	0.453291	0.393589	0.033*
C4	1.0518 (3)	0.1913 (9)	0.33364 (18)	0.0303 (9)
H4	1.104619	0.107792	0.322010	0.036*
C5	0.9720 (3)	0.1072 (9)	0.30721 (18)	0.0304 (9)
H5	0.971216	−0.031349	0.277614	0.036*
C6	0.8934 (3)	0.2228 (8)	0.32348 (17)	0.0260 (8)
H6	0.838874	0.165478	0.305463	0.031*
C7	0.8970 (2)	0.4256 (8)	0.36705 (15)	0.0194 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.01882 (12)	0.01952 (12)	0.01885 (12)	−0.00162 (9)	0.00346 (9)	−0.00136 (9)
I2	0.02741 (13)	0.02835 (14)	0.01735 (12)	0.00846 (10)	−0.00403 (9)	0.00139 (10)
I3	0.01542 (11)	0.03132 (14)	0.02042 (12)	−0.00464 (9)	−0.00022 (9)	−0.00501 (10)
F1	0.0151 (10)	0.0285 (12)	0.0230 (11)	−0.0008 (9)	−0.0039 (8)	−0.0038 (9)
F2	0.0261 (11)	0.0259 (12)	0.0221 (11)	−0.0066 (9)	0.0014 (9)	0.0078 (9)
F3	0.0198 (10)	0.0286 (12)	0.0184 (10)	0.0021 (9)	−0.0027 (8)	0.0066 (9)
C8	0.0174 (16)	0.0146 (17)	0.0163 (16)	−0.0009 (13)	0.0025 (13)	−0.0019 (13)
C9	0.0137 (16)	0.0191 (17)	0.0175 (17)	0.0018 (13)	−0.0010 (13)	−0.0058 (14)
C10	0.0180 (17)	0.0184 (17)	0.0142 (16)	0.0044 (13)	−0.0036 (13)	−0.0014 (14)
C11	0.0206 (18)	0.0202 (18)	0.0180 (17)	−0.0001 (14)	0.0032 (14)	−0.0004 (14)
C12	0.0130 (16)	0.0198 (18)	0.0180 (17)	−0.0001 (13)	0.0000 (13)	−0.0020 (14)
C13	0.0159 (16)	0.0208 (18)	0.0163 (16)	0.0037 (14)	0.0007 (13)	−0.0005 (14)
S1	0.0217 (5)	0.0233 (5)	0.0217 (5)	−0.0019 (4)	0.0019 (4)	−0.0025 (4)
S2	0.0158 (4)	0.0237 (5)	0.0229 (5)	−0.0027 (3)	−0.0021 (3)	−0.0020 (4)
N1	0.0183 (15)	0.0251 (17)	0.0178 (15)	−0.0035 (13)	−0.0019 (12)	−0.0011 (13)
C1	0.0178 (17)	0.0183 (18)	0.0191 (17)	−0.0026 (14)	−0.0004 (14)	0.0025 (14)
C2	0.0218 (18)	0.0196 (18)	0.0194 (18)	0.0014 (14)	−0.0019 (14)	0.0022 (15)
C3	0.0201 (19)	0.033 (2)	0.030 (2)	0.0003 (16)	−0.0023 (16)	0.0032 (18)
C4	0.033 (2)	0.031 (2)	0.028 (2)	0.0097 (18)	0.0072 (17)	0.0002 (18)
C5	0.043 (3)	0.022 (2)	0.026 (2)	0.0013 (18)	0.0067 (18)	−0.0007 (17)
C6	0.033 (2)	0.022 (2)	0.0223 (19)	−0.0059 (16)	−0.0037 (16)	0.0010 (16)
C7	0.0198 (18)	0.0199 (18)	0.0183 (17)	−0.0008 (14)	0.0004 (14)	0.0026 (14)

Geometric parameters (Å, º) top

I1—C8	2.095 (3)	S2—C7	1.742 (4)
I2—C10	2.082 (3)	N1—HN1	0.857 (19)
I3—C12	2.088 (3)	N1—C1	1.353 (5)
F1—C9	1.349 (4)	N1—C2	1.391 (5)
F2—C11	1.343 (4)	C2—C3	1.386 (5)
F3—C13	1.338 (4)	C2—C7	1.402 (5)
C8—C9	1.381 (5)	C3—H3	0.9500
C8—C13	1.389 (5)	C3—C4	1.378 (6)
C9—C10	1.384 (5)	C4—H4	0.9500
C10—C11	1.388 (5)	C4—C5	1.393 (6)
C11—C12	1.384 (5)	C5—H5	0.9500
C12—C13	1.379 (5)	C5—C6	1.390 (6)
S1—C1	1.671 (4)	C6—H6	0.9500
S2—C1	1.743 (4)	C6—C7	1.394 (5)

C9—C8—I1	121.6 (3)	S1—C1—S2	122.8 (2)
C9—C8—C13	117.3 (3)	N1—C1—S1	127.4 (3)
C13—C8—I1	121.1 (3)	N1—C1—S2	109.8 (3)
F1—C9—C8	118.8 (3)	N1—C2—C7	112.1 (3)
F1—C9—C10	118.6 (3)	C3—C2—N1	127.1 (4)
C8—C9—C10	122.6 (3)	C3—C2—C7	120.8 (4)
C9—C10—I2	122.0 (3)	C2—C3—H3	120.8
C9—C10—C11	117.5 (3)	C4—C3—C2	118.5 (4)
C11—C10—I2	120.5 (3)	C4—C3—H3	120.8
F2—C11—C10	118.6 (3)	C3—C4—H4	119.4
F2—C11—C12	119.0 (3)	C3—C4—C5	121.1 (4)
C12—C11—C10	122.3 (3)	C5—C4—H4	119.4
C11—C12—I3	121.9 (3)	C4—C5—H5	119.5
C13—C12—I3	120.5 (3)	C6—C5—C4	121.0 (4)
C13—C12—C11	117.6 (3)	C6—C5—H5	119.5
F3—C13—C8	118.7 (3)	C5—C6—H6	121.0
F3—C13—C12	118.6 (3)	C5—C6—C7	117.9 (4)
C12—C13—C8	122.7 (3)	C7—C6—H6	121.0
C7—S2—C1	92.24 (18)	C2—C7—S2	109.9 (3)
C1—N1—HN1	121 (3)	C6—C7—S2	129.5 (3)
C1—N1—C2	115.9 (3)	C6—C7—C2	120.6 (3)
C2—N1—HN1	123 (3)

I1—C8—C9—F1	−0.5 (4)	C13—C8—C9—F1	177.0 (3)
I1—C8—C9—C10	−178.3 (3)	C13—C8—C9—C10	−0.8 (5)
I1—C8—C13—F3	−0.7 (4)	N1—C2—C3—C4	178.2 (4)
I1—C8—C13—C12	178.0 (3)	N1—C2—C7—S2	−0.2 (4)
I2—C10—C11—F2	0.1 (5)	N1—C2—C7—C6	−178.7 (3)
I2—C10—C11—C12	−178.9 (3)	C1—S2—C7—C2	−0.2 (3)
I3—C12—C13—F3	0.8 (5)	C1—S2—C7—C6	178.1 (4)
I3—C12—C13—C8	−177.9 (3)	C1—N1—C2—C3	−179.4 (4)
F1—C9—C10—I2	1.7 (4)	C1—N1—C2—C7	0.8 (5)
F1—C9—C10—C11	−177.2 (3)	C2—N1—C1—S1	179.2 (3)
F2—C11—C12—I3	−1.4 (5)	C2—N1—C1—S2	−0.9 (4)
F2—C11—C12—C13	−179.3 (3)	C2—C3—C4—C5	1.5 (6)
C8—C9—C10—I2	179.5 (3)	C3—C2—C7—S2	179.9 (3)
C8—C9—C10—C11	0.6 (5)	C3—C2—C7—C6	1.4 (6)
C9—C8—C13—F3	−178.2 (3)	C3—C4—C5—C6	−0.6 (6)
C9—C8—C13—C12	0.4 (5)	C4—C5—C6—C7	0.0 (6)
C9—C10—C11—F2	179.0 (3)	C5—C6—C7—S2	−178.6 (3)
C9—C10—C11—C12	0.0 (5)	C5—C6—C7—C2	−0.4 (6)
C10—C11—C12—I3	177.6 (3)	C7—S2—C1—S1	−179.5 (2)
C10—C11—C12—C13	−0.4 (5)	C7—S2—C1—N1	0.6 (3)
C11—C12—C13—F3	178.8 (3)	C7—C2—C3—C4	−1.9 (6)
C11—C12—C13—C8	0.1 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—HN1···S1ⁱ	0.86 (2)	2.54 (2)	3.389 (3)	172 (4)
C3—H3···I1ⁱⁱ	0.95	3.03	3.928 (4)	159

Symmetry codes: (i) −x+2, −y+2, −z+1; (ii) −x+2, −y+1, −z+1.

1,3-Benzothiazole-2-thiol–1,1,2,2-tetraiodoethene (1/1) (MBZTH_TIE) top

Crystal data top

C₂I₄·C₇H₅NS₂	Z = 2
M_r = 698.86	F(000) = 620
Triclinic, P1	D_x = 3.065 Mg m⁻³
a = 7.4085 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.8180 (9) Å	Cell parameters from 9908 reflections
c = 11.1989 (10) Å	θ = 2.4–27.6°
α = 66.616 (3)°	µ = 8.48 mm⁻¹
β = 70.765 (3)°	T = 100 K
γ = 70.792 (3)°	Block, yellow
V = 757.20 (11) Å³	0.08 × 0.07 × 0.07 mm

Data collection top

Bruker D8 Venture Photon 2 diffractometer	3037 reflections with I > 2σ(I)
Radiation source: Incoatec IµS	R_int = 0.052
φ and ω scans	θ_max = 27.6°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2017)	h = −9→9
T_min = 0.589, T_max = 0.746	k = −14→14
22463 measured reflections	l = −14→14
3484 independent reflections

Refinement top

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) = 0.072	w = 1/[σ²(F_o²) + (0.0264P)² + 3.2353P] where P = (F_o² + 2F_c²)/3
S = 1.13	(Δ/σ)_max = 0.002
3484 reflections	Δρ_max = 1.43 e Å⁻³
159 parameters	Δρ_min = −1.76 e Å⁻³
7 restraints

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
I1	0.18703 (5)	0.90012 (3)	0.68231 (3)	0.02172 (9)
I2	0.32280 (5)	0.95731 (4)	0.33480 (3)	0.02290 (9)
C8	0.0936 (8)	0.9743 (5)	0.5033 (6)	0.0239 (11)
I3	0.72172 (6)	0.21253 (4)	0.95745 (4)	0.03285 (11)
I4	0.76779 (5)	−0.15110 (4)	1.05340 (4)	0.02545 (10)
C9A	0.9080 (15)	0.0083 (10)	1.0028 (9)	0.016 (3)	0.529 (19)
C9B	0.9990 (16)	−0.0669 (12)	1.0232 (11)	0.016 (3)	0.471 (19)
S1	0.33205 (18)	0.46883 (15)	0.92558 (14)	0.0257 (3)
S2	0.34982 (18)	0.53599 (14)	0.63493 (13)	0.0224 (3)
N1	0.0271 (6)	0.5607 (5)	0.8065 (4)	0.0207 (9)
HN1	−0.057 (8)	0.555 (7)	0.881 (4)	0.036 (19)*
C1	0.2213 (7)	0.5214 (5)	0.7989 (5)	0.0193 (10)
C2	0.1323 (7)	0.6027 (5)	0.5783 (5)	0.0189 (10)
C3	0.1076 (8)	0.6481 (6)	0.4478 (6)	0.0245 (11)
H3	0.217056	0.642904	0.374510	0.029*
C4	−0.0808 (9)	0.7004 (6)	0.4295 (6)	0.0270 (12)
H4	−0.101730	0.733475	0.341722	0.032*
C5	−0.2416 (8)	0.7059 (6)	0.5370 (6)	0.0272 (12)
H5	−0.369991	0.742518	0.520859	0.033*
C6	−0.2192 (8)	0.6593 (5)	0.6671 (6)	0.0233 (11)
H6	−0.329217	0.662174	0.740411	0.028*
C7	−0.0280 (7)	0.6081 (5)	0.6852 (5)	0.0187 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.01984 (17)	0.02418 (18)	0.02146 (18)	−0.00095 (13)	−0.00713 (13)	−0.00908 (13)
I2	0.01628 (16)	0.02862 (19)	0.02166 (18)	−0.00312 (13)	−0.00118 (13)	−0.01016 (14)
C8	0.024 (3)	0.020 (2)	0.025 (3)	0.002 (2)	−0.006 (2)	−0.009 (2)
I3	0.0351 (2)	0.0308 (2)	0.0316 (2)	0.01363 (16)	−0.01664 (17)	−0.01885 (16)
I4	0.02582 (18)	0.02565 (18)	0.02593 (19)	−0.01160 (14)	−0.00886 (14)	−0.00245 (14)
C9A	0.020 (5)	0.005 (4)	0.016 (4)	0.003 (4)	−0.004 (3)	−0.001 (3)
C9B	0.009 (5)	0.012 (6)	0.019 (5)	0.003 (4)	−0.004 (4)	−0.003 (4)
S1	0.0144 (6)	0.0329 (7)	0.0213 (6)	0.0021 (5)	−0.0034 (5)	−0.0067 (6)
S2	0.0158 (6)	0.0261 (6)	0.0215 (6)	−0.0002 (5)	−0.0008 (5)	−0.0105 (5)
N1	0.017 (2)	0.021 (2)	0.019 (2)	−0.0026 (17)	−0.0031 (17)	−0.0042 (18)
C1	0.016 (2)	0.015 (2)	0.024 (3)	−0.0034 (18)	−0.004 (2)	−0.005 (2)
C2	0.017 (2)	0.018 (2)	0.022 (3)	−0.0040 (19)	−0.0020 (19)	−0.008 (2)
C3	0.026 (3)	0.026 (3)	0.022 (3)	−0.005 (2)	−0.002 (2)	−0.012 (2)
C4	0.031 (3)	0.024 (3)	0.025 (3)	−0.009 (2)	−0.005 (2)	−0.005 (2)
C5	0.025 (3)	0.021 (3)	0.034 (3)	0.000 (2)	−0.012 (2)	−0.006 (2)
C6	0.019 (2)	0.020 (2)	0.029 (3)	−0.002 (2)	−0.004 (2)	−0.008 (2)
C7	0.020 (2)	0.015 (2)	0.018 (2)	−0.0022 (18)	−0.002 (2)	−0.0051 (19)

Geometric parameters (Å, º) top

I1—C8	2.101 (6)	N1—C1	1.343 (6)
I2—C8	2.106 (6)	N1—C7	1.396 (7)
C8—C8ⁱ	1.329 (11)	C2—C3	1.400 (8)
I3—C9A	2.146 (10)	C2—C7	1.386 (7)
I3—C9Bⁱⁱ	2.166 (11)	C3—H3	0.9500
I4—C9A	2.095 (10)	C3—C4	1.373 (8)
I4—C9B	2.069 (11)	C4—H4	0.9500
C9A—C9Aⁱⁱ	1.30 (2)	C4—C5	1.392 (8)
C9B—C9Bⁱⁱ	1.33 (2)	C5—H5	0.9500
S1—C1	1.682 (5)	C5—C6	1.388 (8)
S2—C1	1.738 (5)	C6—H6	0.9500
S2—C2	1.750 (5)	C6—C7	1.392 (7)
N1—HN1	0.85 (2)

I1—C8—I2	114.1 (2)	C7—C2—S2	109.9 (4)
C8ⁱ—C8—I1	123.2 (6)	C7—C2—C3	121.0 (5)
C8ⁱ—C8—I2	122.8 (6)	C2—C3—H3	121.2
C9A—I3—C9Bⁱⁱ	26.4 (4)	C4—C3—C2	117.6 (5)
I4—C9A—I3	114.6 (5)	C4—C3—H3	121.2
C9Aⁱⁱ—C9A—I3	120.0 (10)	C3—C4—H4	119.4
C9Aⁱⁱ—C9A—I4	125.3 (10)	C3—C4—C5	121.3 (6)
I4—C9B—I3ⁱⁱ	115.8 (5)	C5—C4—H4	119.4
C9Bⁱⁱ—C9B—I4	127.1 (11)	C4—C5—H5	119.2
C1—S2—C2	91.8 (2)	C6—C5—C4	121.7 (5)
C1—N1—HN1	122 (5)	C6—C5—H5	119.2
C1—N1—C7	115.7 (4)	C5—C6—H6	121.5
C7—N1—HN1	122 (5)	C5—C6—C7	116.9 (5)
S1—C1—S2	123.1 (3)	C7—C6—H6	121.5
N1—C1—S1	126.6 (4)	C2—C7—N1	112.4 (4)
N1—C1—S2	110.2 (4)	C2—C7—C6	121.5 (5)
C3—C2—S2	129.1 (4)	C6—C7—N1	126.1 (5)

S2—C2—C3—C4	−178.0 (4)	C3—C2—C7—N1	−178.9 (5)
S2—C2—C7—N1	0.4 (5)	C3—C2—C7—C6	−0.3 (8)
S2—C2—C7—C6	179.0 (4)	C3—C4—C5—C6	0.2 (9)
C1—S2—C2—C3	177.8 (5)	C4—C5—C6—C7	0.7 (8)
C1—S2—C2—C7	−1.4 (4)	C5—C6—C7—N1	177.7 (5)
C1—N1—C7—C2	1.3 (6)	C5—C6—C7—C2	−0.7 (8)
C1—N1—C7—C6	−177.3 (5)	C7—N1—C1—S1	176.2 (4)
C2—S2—C1—S1	−176.4 (3)	C7—N1—C1—S2	−2.3 (6)
C2—S2—C1—N1	2.1 (4)	C7—C2—C3—C4	1.2 (8)
C2—C3—C4—C5	−1.1 (8)

Symmetry codes: (i) −x, −y+2, −z+1; (ii) −x+2, −y, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—HN1···S1ⁱⁱⁱ	0.85 (2)	2.43 (2)	3.275 (5)	170 (6)

Symmetry code: (iii) −x, −y+1, −z+2.

Halogen- and chalcogen-bond geometries (Å, °) top

Compound		d(D···A)	R_XBⁱ	θ(C–D···A)	θ(D···A—C)	θ₁ – θ₂ⁱⁱ	ψⁱⁱⁱ
2(IT)·(1,3-F₄DIB)	I1···S1	3.2265 (6)	0.85	174.51 (4)	113.51 (5)	61.00	0.79
	I2···S1	3.2860 (5)	0.87	176.10 (4)	99.67 (5)	76.43	0.03
(IT)·(1,3,5-F₃I₃B)	I1···I3	3.8376 (6)	0.97	162.95 (8)	106.24 (7)	56.71	0.64
	I2···S1	3.1505 (8)	0.83	171.86 (7)	101.89 (10)	69.97	0.48
	I3···S1	3.1754 (8)	0.84	177.68 (8)	90.59 (9)	87.09	0.18
4(MBZIM)·3(1,3-F₄DIB)	I1···S3	3.3361 (10)	0.88	172.18 (8)	136.86 (8)	35.32	0.83
	I6···S2	3.2150 (9)	0.85	166.06 (8)	134.24 (8)	31.82	0.74
(MBZIM)·(1,4-F₄DIB)	I1···S1	3.2573 (9)	0.86	168.29 (6)	131.28 (8)	37.01	0.57
(MBZIM)·(TIE)	I1···S1	3.5368 (14)	0.94	173.83 (17)	71.37 (16)	102.46	0.66
	I3···S1	3.2702 (14)	0.87	177.05 (17)	118.15 (17)	58.90	0.64
(MMBZIM)·(1,2-F₄DIB)	I1···S1	3.6404 (10)	0.96	154.63 (12)	95.76 (13)	58.87	0.47
	I2···S1	3.2307 (11)	0.85	169.63 (11)	106.66 (15)	62.97	0.04
2(MMBZIM)·(1,4-F₄DIB)·2(H₂O)	I1···S1	3.2516 (4)	0.86	169.16 (4)	96.12 (4)	73.04	0.37
(MMBZIM)·(1,3,5-F₃I₃B)	I2···S1	3.474 (2)	0.92	164.1 (3)	92.1 (3)	72.0	0.71
	I3···S1	3.463 (2)	0.92	176.7 (3)	96.5 (3)	80.2	0.50
(MBZOX)·(1,2-F₄DIB)	I2···S1	3.2853 (19)	0.87	166.65 (19)	105.4 (3)	61.3	0.19
(MBZOX)·(1,3-F₄DIB)	I1···S1	3.4132 (7)	0.90	174.53 (6)	105.63 (8)	68.90	0.19
	I2···S1	3.6787 (6)	0.97	159.40 (6)	92.48 (7)	66.92	0.66
	S1···I1	3.7536 (7)	0.99	160.34 (7)	105.80 (6)	54.54	0.53
2(MBZOX)·(1,4-F₄DIB)	I1···S1	3.2287 (11)	0.85	174.60 (9)	109.39 (13)	65.21	0.74
(MBZOX)·(1,3,5-F₃I₃B)	I1···S1	3.4114 (14)	0.90	171.55 (13)	100.14 (19)	71.41	0.14
	I2···I3	3.9110 (7)	0.99	147.22 (13)	79.55 (13)	67.67	0.62
	I3···S1	3.6774 (13)	0.97	157.67 (15)	95.79 (16)	61.88	0.67
	S1···I1	3.7385 (14)	0.99	163.12 (17)	98.99 (14)	64.13	0.44
3(MBZTH)·4(1,2-F₄DIB)	I1···S5	3.380 (4)	0.89	177.9 (4)	113.3 (5)	64.6	0.81
	I2···S5	3.353 (4)	0.89	163.7 (4)	128.9 (5)	34.8	0.61
	I3···S3	3.371 (5)	0.89	169.0 (4)	96.4 (7)	72.6	0.02
	I4···S3	3.754 (4)	0.99	173.7 (4)	100.5 (6)	73.2	0.76
	I5···S1	3.380 (4)	0.89	177.9 (4)	113.3 (5)	64.6	0.81
	I6···I7	3.8766 (14)	0.95	170.5 (4)	118.1 (4)	52.4	0.73
	I6···S1	3.391 (5)	0.90	168.1 (4)	111.3 (6)	56.8	0.76
(MBZTH)·(1,3-F₄DIB)	I1···S1	3.3724 (5)	0.89	168.06 (6)	120.18 (6)	47.88	0.64
	I2···S1	3.4140 (5)	0.90	157.68 (4)	106.00 (5)	51.68	0.66
(MBZTH)·2(1,3-F₄DIB)	I1···S3	3.3426 (17)	0.88	168.34 (18)	103.3 (2)	65.0	0.25
	I2···S2	3.7429 (17)	0.99	152.94 (18)	121.7 (4)ⁱⁱⁱ	31.2	0.23
	I3···S1	3.3548 (18)	0.89	166.60 (17)	100.3 (2)	66.3	0.64
	I4···S4	3.6744 (17)	0.97	148.74 (18)	118.4 (4)ⁱⁱⁱ	30.4	0.65
	I5···I4	3.7971 (10)	0.96	163.30 (19)	82.92 (18)	80.38	0.52
	I8···I2	3.7950 (9)	0.96	170.03 (18)	84.69 (18)	85.34	0.71
2(MBZTH)·(1,4-F₄DIB)	I1···S1	3.3013 (7)	0.87	178.16 (7)	103.84 (10)	74.32	0.60
(MBZTH)·(1,3,5-F₃I₃B)	I1···S1	3.4551 (10)	0.91	169.01 (9)	97.89 (13)	71.12	0.71
	S2···I3	3.7777 (10)	1.00	158.73 (12)	117.64 (10)	41.09	0.52
(MBZTH)·(TIE)^iv	I1···I3	3.9459 (7)	1.00	171.07 (14)	70.7 (3)	100.4	0.55
	I3···S1	3.2826 (13)	0.87	162.1 (3)	122.51 (19)	39.6	0.41
	I4···S1	3.6514 (19)	0.97	161.9 (3)	77.0 (2)	84.9	0.46

Notes: (i) R_XB = d(X···Y)/Σd(vdW), the ratio of the distance between the donor atom (i.e. I) and the acceptor atom (i.e. S) to the sum of their van der Waals (vdW) radii (S = 1.80 Å and I = 1.98 Å) (Auffinger et al., 2004). (ii) θ₁ – θ₂ = |{[θ(C—D···A)] – [θ(D···A—C)]}|. (iii) Geometries calculated to the primary component of the TIE disorder. (iii) Linearity parameter (Setter et al., 2020). (iv) For interactions in which a thione S atom acts as a halogen-bond acceptor, the average of the two C—S···I angles is used to best represent the location of the maximum electrostatic potential on the S atom. [Two notes (iii). Should they be renumbered or combined?]

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STRUCTURAL
CHEMISTRY

ISSN: 2053-2296

Volume 78| Part 12| December 2022| Pages 702-715

https://doi.org/10.1107/S2053229622009548

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sigma-hole interactions\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

1. Introduction

2. Experimental

2.1. Materials and instrumentation

2.2. Preparation of cocrystals

2.2.1. 2(IT)·(1,3-F4DIB)

2.2.2. (IT)·(1,3,5-F3I3B)

2.2.3. 4(MBZIM)·3(1,3-F4DIB)

2.2.4. (MBZIM)·(1,4-F4DIB)

2.2.5. (MBZIM)·(TIE)

2.2.6. (MMBZIM)·(1,2-F4DIB)

2.2.7. 2(MMBZIM)·(1,4-F4DIB)·2(H2O)

2.2.8. (MMBZIM)·(1,3,5-F3I3B)

2.2.9. (MBZOX)·(1,2-F4DIB)

2.2.10. (MBZOX)·(1,3-F4DIB)

2.2.11. 2(MBZOX)·(1,4-F4DIB)

2.2.12. (MBZOX)·(1,3,5-F3I3B)

2.2.13. 3(MBZTH)·4(1,2-F4DIB)

2.2.14. (MBZTH)·(1,3-F4DIB)

2.2.15. (MBZTH)·2(1,3-F4DIB)

2.2.16. 2(MBZTH)·(1,4-F4DIB)

2.2.17. (MBZTH)·(1,3,5-F3I3B)

2.2.18. (MBZTH)·(TIE)

2.3. Refinement

3. Results and discussion

3.1. Cocrystals of imidazolidine-2-thione (IT)

3.2. Cocrystals of 2-mercaptobenzimidazole (MBZIM)

3.3. Cocrystals of 2-mercapto-5-methyl­benzimidazole (MMBZIM)

3.4. Cocrystals of 2-mercaptobenzoxazole (MBZOX)

3.5. Cocrystals of 2-mercaptobenzo­thia­zole (MBZTH)

4. Conclusion

Supporting information

References

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

2.2.1. 2(IT)·(1,3-F₄DIB)

2.2.2. (IT)·(1,3,5-F₃I₃B)

2.2.3. 4(MBZIM)·3(1,3-F₄DIB)

2.2.4. (MBZIM)·(1,4-F₄DIB)

2.2.6. (MMBZIM)·(1,2-F₄DIB)

2.2.7. 2(MMBZIM)·(1,4-F₄DIB)·2(H₂O)

2.2.8. (MMBZIM)·(1,3,5-F₃I₃B)

2.2.9. (MBZOX)·(1,2-F₄DIB)

2.2.10. (MBZOX)·(1,3-F₄DIB)

2.2.11. 2(MBZOX)·(1,4-F₄DIB)

2.2.12. (MBZOX)·(1,3,5-F₃I₃B)

2.2.13. 3(MBZTH)·4(1,2-F₄DIB)

2.2.14. (MBZTH)·(1,3-F₄DIB)

2.2.15. (MBZTH)·2(1,3-F₄DIB)

2.2.16. 2(MBZTH)·(1,4-F₄DIB)

2.2.17. (MBZTH)·(1,3,5-F₃I₃B)

3.3. Cocrystals of 2-mercapto-5-methylbenzimidazole (MMBZIM)

3.5. Cocrystals of 2-mercaptobenzothiazole (MBZTH)