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The reaction of thiourea and 1,3-dimethylthiourea towards organoiodines: oxidative bond formation and halogen bonding
Acta Crystallographica Section C ( IF 0.7 ) Pub Date : 2021-09-10 , DOI: 10.1107/s205322962100869x Andrew J Peloquin 1 , Arianna C Ragusa 1 , Colin D McMillen 1 , William T Pennington 1
Acta Crystallographica Section C ( IF 0.7 ) Pub Date : 2021-09-10 , DOI: 10.1107/s205322962100869x Andrew J Peloquin 1 , Arianna C Ragusa 1 , Colin D McMillen 1 , William T Pennington 1
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By varying the halogen-bond-donor molecule, 11 new halogen-bonding cocrystals involving thiourea or 1,3-dimethylthiourea were obtained, namely, 1,3-dimethylthiourea–1,2-diiodo-3,4,5,6-tetrafluorobenzene (1/1), C6F4I2·C3H8N2S, 1, thiourea–1,3-diiodo-2,4,5,6-tetrafluorobenzene (1/1), C6F4I2·CH4N2S, 2, 1,3-dimethylthiourea–1,3-diiodo-2,4,5,6-tetrafluorobenzene (1/1), C6F4I2·C3H8N2S, 3, 1,3-dimethylthiourea–1,3-diiodo-2,4,5,6-tetrafluorobenzene–methanol (1/1/1), C6F4I2·C3H8N2S·CH4O, 4, 1,3-dimethylthiourea–1,3-diiodo-2,4,5,6-tetrafluorobenzene–ethanol (1/1/1), C6F4I2·C3H8N2S·C2H6O, 5, 1,3-dimethylthiourea–1,4-diiodo-2,3,5,6-tetrafluorobenzene (1/1), C6F4I2·C3H8N2S, 6, 1,3-dimethylthiourea–1,3,5-trifluoro-2,4,6-triiodobenzene (1/1), C6F3I3·C3H8N2S, 7, 1,3-dimethylthiourea–1,1,2,2-tetraiodoethene (1/1), C6H16N4S2·C2I4, 8, [(dimethylamino)methylidene](1,2,2-triiodoethenyl)sulfonium iodide–1,1,2,2-tetraiodoethene–acetone (1/1/1), C5H8I3N2S+·I−·C3H6O·C2I4, 9, 2-amino-4-methyl-1,3-thiazol-3-ium iodide–1,1,2,2-tetraiodoethene (2/3), 2C4H7N2S+·2I−·3C2I4, 10, and 4,4-dimethyl-4H-1,3,5-thiadiazine-3,5-diium diiodide–1,1,2,2-tetraiodoethene (2/3), 2C5H12N4S2+·4I−·3C2I4, 11. When utilizing the common halogen-bond-donor molecules 1,2-, 1,3-, and 1,4-diiodotetrafluorobenzene, as well as 1,3,5-trifluoro-2,4,6-triiodobenzene, bifurcated I…S…I interactions were observed, resulting in the formation of isolated rings, chains, and sheets. Tetraiodoethylene (TIE) provided I…S…I cocrystals as well, but further yielded a sulfonium-containing product through the reaction of the S atom with TIE. This particular sulfonium motif is the first of its kind to be structurally characterized, and is stabilized in the solid state through a three-dimensional I…I halogen-bonding network. Thiourea reacted with acetone in the presence of TIE to provide two novel heterocyclic products, again stabilized in the solid state through I…I halogen bonding.
中文翻译：
硫脲和 1,3-二甲基硫脲对有机碘的反应：氧化键形成和卤素键合
通过改变卤键供体分子，获得了11个新的含硫脲或1,3-二甲基硫脲的卤键共晶，即1,3-二甲基硫脲-1,2-二碘-3,4,5,6-四氟苯(1/1), C 6 F 4 I 2 ·C 3 H 8 N 2 S, 1 , 硫脲–1,3-二碘-2,4,5,6-四氟苯 (1/1), C 6 F 4 I 2 ·CH 4 N 2 S, 2 , 1,3-二甲基硫脲–1,3-二碘-2,4,5,6-四氟苯 (1/1), C 6 F 4 I 2 ·C 3 H 8 N2 S, 3 , 1,3-二甲基硫脲-1,3-二碘-2,4,5,6-四氟苯-甲醇 (1/1/1), C 6 F 4 I 2 ·C 3 H 8 N 2 S ·CH 4 O, 4 , 1,3-二甲基硫脲-1,3-二碘-2,4,5,6-四氟苯-乙醇 (1/1/1), C 6 F 4 I 2 ·C 3 H 8 N 2 S·C 2 H 6 O, 5 , 1,3-二甲基硫脲–1,4-二碘-2,3,5,6-四氟苯 (1/1), C 6 F 4 I 2 ·C3 H 8 N 2 S, 6 , 1,3-二甲基硫脲–1,3,5-三氟-2,4,6-三碘苯 (1/1), C 6 F 3 I 3 ·C 3 H 8 N 2 S , 7 , 1,3-二甲基硫脲–1,1,2,2-四碘乙烯 (1/1), C 6 H 16 N 4 S 2 ·C 2 I 4 , 8 , [(二甲氨基)亚甲基](1,2 ,2-三碘乙烯)碘化锍–1,1,2,2-四碘乙烯–丙酮 (1/1/1), C 5 H 8 I 3 N 2 S+ ·I − ·C 3 H 6 O·C 2 I 4 , 9 , 2-amino-4-methyl-1,3-thiazol-3-ium iodide–1,1,2,2-tetraiodoethene (2/3 ), 2C 4 H 7 N 2 S + ·2I − ·3C 2 I 4 , 10 , 和 4,4-二甲基-4 H -1,3,5-噻二嗪-3,5-二碘化二鎓–1,1, 2,2-四碘乙烯 (2/3), 2C 5 H 12 N 4 S 2+ ·4I - ·3C 2 I 4 , 11. 当使用常见的卤素键供体分子 1,2-、1,3- 和 1,4-二碘四氟苯以及 1,3,5-三氟-2,4,6-三碘苯时，分叉的 I…S ……观察到相互作用，导致形成孤立的环、链和片。四碘乙烯 (TIE) 也提供了 I…S…I 共晶，但通过 S 原子与 TIE 的反应进一步产生了含锍的产物。这种特殊的锍基序是同类中第一个进行结构表征的，并通过三维 I…I 卤素键网络稳定在固态中。硫脲在 TIE 存在下与丙酮反应，提供两种新型杂环产物，再次通过 I…I 卤素键合稳定在固态。
更新日期：2021-10-06
中文翻译：
硫脲和 1,3-二甲基硫脲对有机碘的反应：氧化键形成和卤素键合
通过改变卤键供体分子，获得了11个新的含硫脲或1,3-二甲基硫脲的卤键共晶，即1,3-二甲基硫脲-1,2-二碘-3,4,5,6-四氟苯(1/1), C 6 F 4 I 2 ·C 3 H 8 N 2 S, 1 , 硫脲–1,3-二碘-2,4,5,6-四氟苯 (1/1), C 6 F 4 I 2 ·CH 4 N 2 S, 2 , 1,3-二甲基硫脲–1,3-二碘-2,4,5,6-四氟苯 (1/1), C 6 F 4 I 2 ·C 3 H 8 N2 S, 3 , 1,3-二甲基硫脲-1,3-二碘-2,4,5,6-四氟苯-甲醇 (1/1/1), C 6 F 4 I 2 ·C 3 H 8 N 2 S ·CH 4 O, 4 , 1,3-二甲基硫脲-1,3-二碘-2,4,5,6-四氟苯-乙醇 (1/1/1), C 6 F 4 I 2 ·C 3 H 8 N 2 S·C 2 H 6 O, 5 , 1,3-二甲基硫脲–1,4-二碘-2,3,5,6-四氟苯 (1/1), C 6 F 4 I 2 ·C3 H 8 N 2 S, 6 , 1,3-二甲基硫脲–1,3,5-三氟-2,4,6-三碘苯 (1/1), C 6 F 3 I 3 ·C 3 H 8 N 2 S , 7 , 1,3-二甲基硫脲–1,1,2,2-四碘乙烯 (1/1), C 6 H 16 N 4 S 2 ·C 2 I 4 , 8 , [(二甲氨基)亚甲基](1,2 ,2-三碘乙烯)碘化锍–1,1,2,2-四碘乙烯–丙酮 (1/1/1), C 5 H 8 I 3 N 2 S+ ·I − ·C 3 H 6 O·C 2 I 4 , 9 , 2-amino-4-methyl-1,3-thiazol-3-ium iodide–1,1,2,2-tetraiodoethene (2/3 ), 2C 4 H 7 N 2 S + ·2I − ·3C 2 I 4 , 10 , 和 4,4-二甲基-4 H -1,3,5-噻二嗪-3,5-二碘化二鎓–1,1, 2,2-四碘乙烯 (2/3), 2C 5 H 12 N 4 S 2+ ·4I - ·3C 2 I 4 , 11. 当使用常见的卤素键供体分子 1,2-、1,3- 和 1,4-二碘四氟苯以及 1,3,5-三氟-2,4,6-三碘苯时，分叉的 I…S ……观察到相互作用，导致形成孤立的环、链和片。四碘乙烯 (TIE) 也提供了 I…S…I 共晶，但通过 S 原子与 TIE 的反应进一步产生了含锍的产物。这种特殊的锍基序是同类中第一个进行结构表征的，并通过三维 I…I 卤素键网络稳定在固态中。硫脲在 TIE 存在下与丙酮反应，提供两种新型杂环产物，再次通过 I…I 卤素键合稳定在固态。
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