Halogen bonded dimers and ribbons from the self-assembly of 3-halobenzophenones Patricia A. A. M. Vaz, João Rocha, Artur M. S. Silva and Samuel Guieu

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1 Electronic Supplementary Material (ES) for CrystEngComm. This journal is The Royal Society of Chemistry 27 Halogen bonded dimers and ribbons from the self-assembly of -halobenzophenones Patricia A. A. M. Vaz, João Rocha, Artur M. S. Silva and Samuel Guieu Synthesis...2 General...2 -omo-4,4 -di(dimethylamino)benzophenone...2, -Dibromo-4,4 -di(dimethylamino)benzophenone [-omo-4-(dimethylamino)phenyl][-bromo-4-(methylamino)phenyl]methanone..., -Dibromo-4,4 -dimethoxybenzophenone 5... [4-(Dimethylamino)--iodophenyl][4-(dimethylamino)phenyl]methanone 4 and [4-(dimethylamino)-- iodophenyl][-iodo-4-(methylamino)phenyl]methanone 6... MR spectra...5 Crystal structures...

2 Synthesis General Melting points were determined on a BUCH Melting point apparatus and are uncorrected. H and C MR spectra were recorded on uker or 5 [. MHz ( H), MHz ( C) or 5. MHz ( H), MHz ( C)] spectrometers with TMS as internal reference. Data for H MR are recorded as follows: chemical shift (δ, ppm), multiplicity [s (singlet), d (doublet), t (triplet), q (quartet) and m (multiplet)], and coupling constant (J, Hz) and integration. Data for C MR are reported in terms of chemical shift (δ, ppm). Unequivocal H assignments were made with aid of 2D CSY ( H/ H), while C assignments were made on the basis of 2D HSQC ( H/ C) and HMBC experiments. Elemental analyses were obtained with a Carlo Erba 8 CHS analyzer. High resolution mass spectra analysis (HRMS- ES) were performed on a microtf (focus) mass spectrometer (uker Daltonics, emen, Germany). ons were generated using an Apollo (ES) source. onization was achieved by electrospray, using a voltage of 45 V applied to the needle, and a counter voltage between and 5 V applied to the capillary. Silica gel 6 F254 (Merck) was used for TLC, and the spots were detected with UV light (254 nm). Flash column chromatography was carried out on silica gel 6 (Merck). -omo-4,4 -di(dimethylamino)benzophenone -omosuccinimide (56 mg, 2. mmol, equiv) was slowly added to a solution of Michler s ketone (54 mg, 2. mmol, equiv) in dichloromethane ( ml). After stirring at room temperature for 2 h, water ( ml) was added, and the aqueous phase was extracted with dichloromethane ( x ml). The combined organic phases were dried over MgS 4, filtered, and concentrated under reduced pressure. Silica gel flash column chromatography (eluent: dichloromethane) of the residue gave the compound as a pale yellow solid (4 mg,.5 mmol, 58% yield). Slow evaporation of a dichloromethane solution of the compound afforded pale yellow crystals suitable for XRD. Melting point: -ºC. H MR (. MHz, CDCl, 25 ºC): 7.97 (d, 4 J H-H 2. Hz, H, aromatic CH), 7.77 (d, J H-H 9. Hz, 2H, aromatic CH), 7.67 (dd, 4 J H-H 2., J H-H 8.4 Hz, H, aromatic CH), 7. (d, J H-H 8.4 Hz, H, aromatic CH), 6.7 (d, J H-H 9. Hz, 2H, aromatic CH),.8 (s, 6H, CH ), 2.9 (s, 6H, CH ); C MR (75.47 MHz, CDCl, 25ºC): 92.6 (C=), 54., 5., 5.6, 4., 2.4, 29.8, 24.7, 9.2, 7.,.6, 4.7, 4.; ES + -MS: m/z: 47 [M] + (C 7 H 9 2 ), 49 [M] + (C 7 H ). Anal. Calcd for C 7 H 9 2 : C, 58.8; H, 5.52;, 8.7. Found: C, 59.2; H, 5.7;, 7.76%., -Dibromo-4,4 -di(dimethylamino)benzophenone 2 -omosuccinimide (266 mg,.5 mmol, 2 equiv) was slowly added to a solution of Michler s ketone (2 mg,.75 mmol, equiv) in dichloromethane ( ml). After stirring at room temperature for 2 h, water ( ml) was added, and the aqueous phase was extracted with dichloromethane ( x ml). The combined organic phases were dried over MgS 4, filtered, and concentrated under reduced pressure. Silica gel flash column chromatography (eluent: dichloromethane) of the residue gave the compound as a pale yellow solid (264 mg,.62 mmol, 8% yield). Slow evaporation of a dichloromethane solution of the compound afforded pale yellow crystals suitable for XRD. Melting point: 28-ºC. H MR (. MHz, CDCl, 25 ºC): 8. (d, 4 J H-H 2. Hz, 2H, aromatic CH), 7.68 (dd, 4 J H-H 2., J H-H 8.4 Hz, 2H, aromatic CH), 7.6 (d, J H-H 8.4 Hz, 2H, aromatic CH), 2.9 (s, 2H, CH ); C MR (75.47 MHz, CDCl, 25ºC): = 9.9 (C=), 55., 6., 2.,.2, 9., 6.8, 4.6; ES + -MS: m/z: 425 [M+H] + (C 7 H ), 427 [M+H] + (C 7 H ), 429 [M+H] + (C 7 H ). Anal. Calcd for C 7 H : C, 47.9; H, 4.26;, Found: C, 47.; H, 4.27;, 6.2%.

3 [-omo-4-(dimethylamino)phenyl][-bromo-4-(methylamino)phenyl]methanone H omine (6 equiv, 6 mmol, 9 μl) was slowly added to Michler s ketone ( equiv, mmol, 268 mg) in a round bottom flask under nitrogen at room temperature. After stirring at room temperature for 2 min, ethanol ( ml) was added at ºC and the solution was stirred at room temperature for min. Saturated aqueous sodium thiosulfate ( ml) was added slowly at ºC, and the solid that formed was extracted with dichloromethane ( x ml), the organic phases were dried over sodium sulfate, filtered, and evaporated to dryness. Thin layer chromatography (eluent: hexane/dichloromethane, /) of the residue gave compound as a yellow solid (8 mg,.9 mmol, 2 % yield). Slow evaporation of a dichloromethane solution of the compounds afforded pale yellow crystals suitable for XRD. H MR (. MHz, CDCl, 25 ºC): 7.98 (d, 4 J H-H 2. Hz, H, aromatic CH), 7.97 (d, 4 J H-H 2. Hz, H, aromatic CH), 7.7 (dd, J H-H 8.5, 4 J H-H 2. Hz, H, aromatic CH), 7.65 (dd, J H-H 8., 4 J H-H 2. Hz, H, aromatic CH), 7.7 (d, J H-H 8., H, aromatic CH), 6.62 (d, J H-H 8.5, H, aromatic CH), 2.98 (s, H, HCH ), 2.9 (s, 6H, (CH ) 2 ); The quantity was too low to record a C MR spectrum. ES + -MS: m/z: 4 [M+H] + (C 6 H ), 4 [M+H] + (C 6 H ), 45 [M+H] + (C 6 H ). ES + - HRMS: calculated for (C 6 H ): , found: , calculated for (C 6 H ): , found: , calculated for (C 6 H ): , found: Melting point: The quantity was too low., -Dibromo-4,4 -dimethoxybenzophenone 5 4,4 -Dimethoxybenzophenone (commercial by Aldrich) ( equiv, mmol, 242 mg) was set up in a round bottom flask under nitrogen at room temperature. omine ( equiv, mmol, 55 μl) was added slowly and the red slurry was stirred for 2 min. Ethanol ( ml) was added slowly at ºC, and the resulting solution was stirred at room temperature for min. Saturated aqueous sodium thiosulfate ( ml) was added slowly at ºC, and the solid that formed was collected by filtration, washed with water and ethanol. The product was obtained as a white microcrystalline solid (mg, 75% yield). Slow evaporation from dichloromethane gave crystals suitable for single crystal XRD. Melting point: 2-4ºC. H MR (. MHz, CDCl, 25 ºC): 8.2 (d, 4 J H-H 2. Hz, 2H, aromatic CH), 7.74 (dd, 4 J H-H 2., J H-H 8.5 Hz, 2H, aromatic CH), 6.97 (d, J H-H 8.5 Hz, 2H, aromatic CH),.99 (s, 6H, CH ); C MR (75.47 MHz, CDCl, 25ºC): = 92. (C=), 59., 5.,.,.8,.9,., 56.7; ES + -MS: m/z: 99 [M+H] + (C 5 H 2 ), 4 [M+H] + (C 5 H 8 ), 4 [M+H] + (C 5 H 8 2 ). ES + -HRMS: calculated for (C 5 H 2 ): 98.92, found: , calculated for (C 5 H 8 ): 4.926, found: 4.999, calculated for (C 5 H 8 2 ): , found: [4-(Dimethylamino)--iodophenyl][4-(dimethylamino)phenyl]methanone 4 and [4-(dimethylamino)-- iodophenyl][-iodo-4-(methylamino)phenyl]methanone 6 H A mixture of Michler s ketone (.9 mmol, 25 mg, equiv), acl ( ml), wet Si 2 (5% w/w, g) and iodine (.9 mmol, 26 mg, equiv) was stirred at room temperature in CH 2 Cl 2 for 72 h. The reaction mixture was filtered and washed with 5% aqueous sodium thiosulfate solution ( x ml). The aqueous phase was extracted with dichloromethane ( x ml). The combined organic phases were dried over MgS 4, filtered, and concentrated under reduced pressure. Thin layer chromatography (eluent: dichloromethane) of the residue gave the compounds [4-(dimethylamino)--iodophenyl][4- (dimethylamino)phenyl]methanone as a brown solid ( mg,.8 mmol, 9% yield) and [4- (dimethylamino)--iodophenyl][(-iodo-4-(methylamino)phenyl]methanone (5 mg,.29 mmol, %

4 yield). Slow evaporation of a dichloromethane solution of the compounds afforded brown crystals suitable for XRD. [4-(dimethylamino)--iodophenyl][4-(dimethylamino)phenyl]methanone 4 H MR (. MHz, CDCl, 25 ºC): 8.24 (d, 4 J H-H 2. Hz, H, aromatic CH), 7.77 (d, J H-H 9. Hz, 2H, aromatic CH), 7.7 (dd, 4 J H-H 2., J H-H 8. Hz, H, aromatic CH), 7.7 (d, J H-H 8. Hz, H, aromatic CH), 6.69 (d, J H-H 9. Hz, 2H, aromatic CH),.8 (s, 6H, CH ), 2.86 (s, 6H, CH ); C MR (75.47 MHz, CDCl, 25ºC): 92. (C=), 6.9, 5., 42.9, 4.8,., 2.4, 2.4,.2,.,., 29.8, 2.7, 44.6, 44.4; ES + -MS: m/z: 95 [M+H] + (C 7 H 2 2 ). ES + -HRMS: calculated for (C 7 H 2 2 ): , found: Melting point: The quantity was too low. [4-(dimethylamino)--iodophenyl][-iodo-4-(methylamino)phenyl]methanone 6 H H MR (. MHz, CDCl, 25 ºC): (m, 2H, aromatic CH), 8.9 (d, 4 J H-H.8 Hz, H, aromatic CH), 8.8 (d, 4 J H-H.9 Hz, H, aromatic CH), 7.69 (dd, 4 J H-H.9, J H-H 9.7 Hz, H, aromatic CH), 6.54 (d, J H-H 8.6 Hz, H, aromatic CH),.42 (s, 6H, CH ),. (s, H, CH ); C MR (75.47 MHz, CDCl, 25ºC): 95.2 (C=), 7.4, 56.5, 5.6, 4.7, 42.6, 42.4, 4.7,.,.9, 8., 44.8,.9; ES + -MS: m/z: 57 [M+H] + (C 6 H ). ES + -HRMS: calculated for (C 6 H ): , found: Melting point: The quantity was too low.

5 MR spectra CH 2 Cl 2 Acetone f (ppm) Figure S. H MR spectrum of -bromo-4,4 -di(dimethylamino)benzophenone in CDCl f (ppm) Figure S2. C MR spectrum of -bromo-4,4 -di(dimethylamino)benzophenone in CDCl

6 Water f (ppm) Figure S. H MR spectrum of, -dibromo-4,4 -di(dimethylamino)benzophenone 2 in CDCl f (ppm) Figure S4. C MR spectrum of, -dibromo-4,4 -di(dimethylamino)benzophenone 2 in CDCl

7 f (ppm) Figure S5. H MR spectrum of [-bromo-4-(dimethylamino)phenyl][(-bromo-4- (methylamino)phenyl]methanone in CDCl Acetone Water f (ppm) Figure S6. H MR spectrum of, -dibromo-4,4 -dimethoxybenzophenone 5 in CDCl

8 f (ppm) Figure S7. C MR spectrum of, -dibromo-4,4 -dimethoxybenzophenone 5 in CDCl Water Figure S8. H MR spectrum of [4-(dimethylamino)--iodophenyl][4- (dimethylamino)phenyl]methanone 4 in CDCl

9 Figure S9. C MR spectrum of [4-(dimethylamino)--iodophenyl][4- (dimethylamino)phenyl]methanone 4 in CDCl ppm Figure S. H MR spectrum of [4-(dimethylamino)--iodophenyl][-iodo-4- (methylamino)phenyl]methanone 6 in CDCl

10 f (ppm) Figure S. C MR spectrum of [4-(dimethylamino)--iodophenyl][-iodo-4- (methylamino)phenyl)methanone 6 in CDCl Crystal structures Single-crystals were manually selected from the crystallization vial. A suitable single-crystal was mounted on a glass fiber with the help of silicon grease. Data were collected at 8(2) K on a uker X8 Kappa APEX charge-coupled device (CCD) area-detector diffractometer (Mo K a graphitemonochromated radiation, λ =.77 Å) controlled by the APEX2 software package, and equipped with an xford Cryosystems Series 7 cryostream monitored remotely using the software interface Cryopad. 2 mages were processed using the software package SAT+, and data were corrected for absorption by the multi-scan semi-empirical method implemented in SADABS. 4 The structure was solved using the direct methods algorithm implemented in SHELXS-97, 5,6 which allowed the immediate location of the majority of the atoms. All remaining non-hydrogen atoms were located from difference Fourier maps calculated from successive full-matrix least squares refinement cycles on F 2 using SHELXL-97. 5,7 All non-hydrogen atoms were successfully refined using anisotropic displacement parameters. Hydrogen atoms bound to carbon were located at their idealized positions using appropriate HFX instructions in SHELXL (4 for the aromatic and vinylic, 2 for the CH 2 moieties and for the chiral tertiary carbon atoms) and included in subsequent refinement cycles in riding-motion approximation with isotropic thermal displacements parameters (U iso ) fixed at.2 times U eq of the atom to which they are attached. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication o. CCDC , CCDC and CCDC Copies of the data can be obtained free of charge on application to CCDC, 2 Union Road, Cambridge CB2 2EZ, U.K. Fax: (+44) () APEX2, Data Collection Software Version 2.-RC, uker AXS, Delft, The etherlands 26. (2) Cryopad, Remote monitoring and control, Version.45, xford Cryosystems, xford, United Kingdom 26. () SAT +, Data ntegration Engine v. 7.2a , uker AXS, Madison, Wisconsin, USA. (4) G. M. Sheldrick, SADABS v.2., uker/siemens Area Detector Absorption Correction Program 998, uker AXS, Madison, Wisconsin, USA. (5) G. M. Sheldrick, Acta Cryst. A, 28, 64, (6) G. M. Sheldrick, SHELXS-97, Program for Crystal Structure Solution, University of Göttingen 997.

11 (7) G. M. Sheldrick, SHELXL-97, Program for Crystal Structure Refinement, University of Göttingen 997.

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