The structure of the new insect-growth regulator 1,4-bis(5-chloropent-4-ynyloxy)benzene

Abstract

The structure of the new insect-growth regulator 1,4-bis(5-chloropent-4-ynyloxy)benzene, C 16 H16C1202, has been determined from 602 diffractometer data. Crystals are monoclinic, space group P2Jn, a = 4.691 (2)

Definition of the Halogen Bond (IUPAC Recommendations 2013): A Revisit

“…• the axial outer portion on the side of X in NX 3 , 186 as well as XCN and XCCCN (X = F, Cl, Br, I, At); 68 • the axial outer portion on the side of halogen X in haloethene C 2 X 4 , 187 C 6 H 5 X, and C 6 X 6 (X = Cl, Br, I); • the axial outer portion of halogen X in −NO 2 substituted arene moieties (as in 1,3,5-triiodo-2,4,6-trinitrobenzene, 188 2-chloro-1-iodo-4-nitronaphthalene, 189 and 1,3,5-trichloro-2,4,6-trinitrobenzene); 190 • the axial outer portion of halogen in haloalkynes, such as the arene derivatives (C 2 I 2 , 191 haloprogin (C 9 H 4 -Cl 3 IO), 192 and 1-halo-2-phenylacetylene (C 8 H 5 X (X = Br, I)), 193 1-fluoro-4-(iodobutadiynyl)benzene (C 10 H 4 -FI), 194 2,6-bis(iodoethynyl)pyridine (C 9 H 3 I 2 N), 195 3iodo-2-propynyl-N-butylcarbamate, 196 3-(iodoethynyl)benzoic acid (C 9 H 5 IO 2 ), 197 2-(bromoethynyl)-1,3-dichlorobenzene (C 8 H 3 BrCl 2 ), 198 1,4-difluoro-2,5-bis-(iodoethynyl)benzene (C 10 H 2 F 2 I 2 ), 199 1,4-bis(iodoethynyl)benzene (C 10 H 4 I 2 ), 200 2,3-bis(bromoethynyl)-1,4-dimethoxybenzene, 201 2,2′,4,4′,6,6′-hexafluoro-3,3′,5,5′-tetrakis(iodoethynyl)biphenyl (C 20 F 6 I 4 ), 202 1,3,5-tris(bromoethynyl)benzene (C 12 H 3 Br 3 ), 203 1,1′,1″,1‴-methanetetrayltetrakis[4-(iodoethynyl)benzene] (C 33 H 16 I 4 ), 204 1,3,5-trifluoro-2,4,6-tris(iodoethynyl)benzene (C 12 F 3 I 3 ), 205 1,4-bis(5-chloro-pent-4-ynyloxy)benzene (C 16 H 16 Cl 2 O 2 ), 206 • the halogen derivative in cations, e.g., fluoroammonium (FNH 3 + ), 231 3-(iodoethynyl)pyridin-1-ium (C 7 H 5 -IN + ), 232 5-bromosulfenyl-1,3,2,4-dithiadiazolium (CBrN 2 S 3 + ), 233 2-(iodoethynyl)pyridinium (C 7 H 5 -IN + ), 232 2-chlorodibenzo[b,d]bromol-5-ium (C 12 H 7 -BrCl + ), 234 1,2,3,4-tetrafluorodibenzo[b,d]iodol-5-ium (C 12 H 4 F 4 I + ), 235 bis(pentafluorophenyl)iodonium (C 12 -F 10 I + ), 236 [4-(ethoxycarbonyl)phenyl](phenyl)iodanium (C 15 H 14 IO 2 + ), 237 and bis(4-chlorophenyl)iodanium (C 12 H 8 Cl 2 I + ). 238 The HaB acceptor entit...…”

“…The HaB donor entity X in R–X may be the axial outer portion on the side of halogen atom X in hydrogen halides HX (X = Br, Cl, I, At) and haloalkanes (CH 3 X, CH 2 X 2 , CHX 3 (X = Cl, Br, I, At), CX 4 (X = F, Cl, Br, I, At), and C n F 2 n +1 I); the axial outer portion on the side of X in OX 2 and in dihalogen molecules X 2 and XX′ (X, X′ = F, Cl, Br, I, At); the axial outer portion on the side of X in NX 3 , as well as XCN and XCCCN (X = F, Cl, Br, I, At); the axial outer portion on the side of halogen X in halo­ethene C 2 X 4 , C 6 H 5 X, and C 6 X 6 (X = Cl, Br, I); the axial outer portion of halogen X in −NO 2 substituted arene moieties (as in 1,­3,5-tri­iodo-2,­4,6-tri­nitro­benz­ene, 2-chloro-1-iodo-4-nitro­naphth­alene, and 1,3,5-tri­chloro-2,4,6-tri­nitro­benz­ene); the axial outer portion of halogen in halo­alkynes, such as the arene derivatives (C 2 ­I 2 , halo­progin (C 9 ­H 4 ­Cl 3 IO), and 1-halo-2-phen­yl­acetyl­ene (C 8 ­H 5 ­X (X = Br, I)), 1-fluoro-4-(iodo­buta­diyn­yl)­benz­ene (C 10 ­H 4 ­FI), 2,6-bis­(iodo­ethyn­yl)­pyri­dine (C 9 ­H 3 ­I 2 ­N), 3-iodo-2-propyn­yl- N -butyl­carbam­ate, 3-(iodo­ethyn­yl)­benz­oic acid (C 9 ­H 5 ­IO 2 ), 2-(bromo­ethyn­yl)-1,3-di­chloro­benz­ene (C 8 ­H 3 ­BrCl 2 ), 1,4-di­fluoro-2,5-bis­(iodo­ethyn­yl)­benz­ene (C 10 ­H 2 ­F 2 ­I 2 ), 1,4-bis­(iodo­ethyn­yl)­benz­ene (C 10 ­H 4 ­I 2 ), 2,3-bis­(bromo­ethyn­yl)-1,4-di­meth­oxy­benz­ene, 2,2′,­4,4′,­6,6′-hexa­fluoro-3,3′,­5,5′-tetra­kis­(iodo­ethyn­yl)­bi­phen­yl (C 20 ­F 6 ­I 4 ), 1,3,5-tris­(bromo­ethyn­yl)­benzene (C 12 ­H 3 ­Br 3 ), 1,1′,1″,1‴-meth­ane­tetra­yl­tetra­kis­[4-(iodo­ethyn­yl)­benz­ene] (C 33 ­H 16 ­I 4 ), 1,3,5-tri­fluoro-2,4,6-tris­(iodo­ethyn­yl)­benz­ene (C 12 ­F 3 ­I 3 ), 1,4-bis­(5-chloro-pent-4-yn­yl­oxy)­benz­ene (C 16 ­H 16 ­Cl 2 ­O 2 ), 2,6-bis­(iodo­ethyn­yl)­pyrid­ine (C 9 ­H 3 ­I 2 ), 2,3,­5,6-tetra­fluoro-1,4-bis­(iodo­ethyn­yl)­benz­ene (C 10 ­F 4 ­I 2 ), and 3-(iodo­ethyn­yl)­pyrid­ine (C 7 ­H 4 ­IN)); hypervalent halogen derivative in molecules, as in (di­chloro-tri­fluoro­meth­yl)­iodine (CCl 2 ­F 3 I), di­chloro­(phen­yl)­iodane (C 6 ­H 5 ­Cl 2 I), o -(di­chlor­iodo)­nitro­benz­ene (C 6 H 4 ­Cl 2 ­INO 2 ), p -(di­chlor­iodo)­nitro­benz­ene (C 6 ­H 4 ­Cl 2 ­INO 2 ), 2-(di­chloro­iodo)­pyrid­ine (C 5 ­H 4 Cl 2 IN), bis­(penta­fluoro­phen­yl)­iodon­ium tri­fluoro­acetate (C 14 ­F 13 ­IO 2 ), tri­fluoro­meth­yl-tetra­fluoro-iodine (CF 7 I), and penta­fluoro­phen­yl-tetra­kis­(fluoro)­iodine (C 6 ­F 9 I)); the halogen in imide and amide derivatives such as N , N ′-di­bromo­ethane­di-imido­yl-di­fluoride (C 2 ­Br 2 ­F 2 ­N 2 ) and 1-chloro­pyrrol­idine-2,5-dione (C 4 ­H 4 ­ClN...…”

“…the axial outer portion of halogen in halo­alkynes, such as the arene derivatives (C 2 ­I 2 , halo­progin (C 9 ­H 4 ­Cl 3 IO), and 1-halo-2-phen­yl­acetyl­ene (C 8 ­H 5 ­X (X = Br, I)), 1-fluoro-4-(iodo­buta­diyn­yl)­benz­ene (C 10 ­H 4 ­FI), 2,6-bis­(iodo­ethyn­yl)­pyri­dine (C 9 ­H 3 ­I 2 ­N), 3-iodo-2-propyn­yl- N -butyl­carbam­ate, 3-(iodo­ethyn­yl)­benz­oic acid (C 9 ­H 5 ­IO 2 ), 2-(bromo­ethyn­yl)-1,3-di­chloro­benz­ene (C 8 ­H 3 ­BrCl 2 ), 1,4-di­fluoro-2,5-bis­(iodo­ethyn­yl)­benz­ene (C 10 ­H 2 ­F 2 ­I 2 ), 1,4-bis­(iodo­ethyn­yl)­benz­ene (C 10 ­H 4 ­I 2 ), 2,3-bis­(bromo­ethyn­yl)-1,4-di­meth­oxy­benz­ene, 2,2′,­4,4′,­6,6′-hexa­fluoro-3,3′,­5,5′-tetra­kis­(iodo­ethyn­yl)­bi­phen­yl (C 20 ­F 6 ­I 4 ), 1,3,5-tris­(bromo­ethyn­yl)­benzene (C 12 ­H 3 ­Br 3 ), 1,1′,1″,1‴-meth­ane­tetra­yl­tetra­kis­[4-(iodo­ethyn­yl)­benz­ene] (C 33 ­H 16 ­I 4 ), 1,3,5-tri­fluoro-2,4,6-tris­(iodo­ethyn­yl)­benz­ene (C 12 ­F 3 ­I 3 ), 1,4-bis­(5-chloro-pent-4-yn­yl­oxy)­benz­ene (C 16 ­H 16 ­Cl 2 ­O 2 ), 2,6-bis­(iodo­ethyn­yl)­pyrid­ine (C 9 ­H 3 ­I 2 ), 2,3,­5,6-tetra­fluoro-1,4-bis­(iodo­ethyn­yl)­benz­ene (C 10 ­F 4 ­I 2 ), and 3-(iodo­ethyn­yl)­pyrid­ine (C 7 ­H 4 ­IN));…”