Physicochemical and Mechanical Properties of Paracetamol Cocrystal with 5-Nitroisopthalic Acid

Supplementary data

Physicochemical and mechanical properties of paracetamol cocrystal with 5-nitroisopthalic acid

StevanusHiendrawan,BambangVeriansyah,EdwardWidjojokusumo,SundaniNuronoSoewandhi,SalehWikarsa,RaymondR.Tjandrawinata

Table S1. ParticlesizedistributionforPCA,andPCA-5NIP

Sample / d(0.1) µm / d(0.5) µm / d(0.9) µm / d[4,3] µm / SPAN
PCA / 3.97 ± 0.115 / 17.32 ± 0.639 / 112.06 ± 12.659 / 41.57 ± 4.887 / 6.23 ± 0.494
PCA-5NIP / 2.91 ± 0.018 / 17.02 ± 1.460 / 105.12 ± 8.558 / 38.09 ± 0.911 / 6.05 ± 1.021

Fig. S1. Powder X-ray diffractograms of (a) PCA, (b) 5NIP, (c) PCA-5NIP from complete solvent evaporation experiment and (d) PCA-5NIP from incomplete solvent evaporation experiment. Notice that the PCA-5NIP obtained from incomplete solvent evaporation experiment was similar to that of PCA-5NIP obtained from complete solvent evaporation.

Fig. S2. DSC thermograms of (a) PCA, (b) 5NIP, (c) physical mixture of PCA:5NIP (1:1 mol ratio), (d) PCA-5NIP from complete solvent evaporation experiment and (e) PCA-5NIP from incomplete solvent evaporation experiment. DSC analysis of cocrystal product from incomplete solvent evaporation experiment showed broad endothermic peak in the temperature range of 50-100 oC which indicate loss of the methanol solvent, the second endotherm in the DSC analysis corresponds to the melting point of PCA-5NIP cocrystal.

Fig. S3. FTIR spectra of (a) PCA, (b) 5NIP, (c) PCA-5NIP from complete solvent evaporation experiment and (d) PCA-5NIP from incomplete solvent evaporation experiment in the frequency region 4000-2000 cm-1 (A) and 2000-700 cm-1 (B). Notice that the PCA-5NIP obtained from incomplete solvent evaporation experiment was similar to that of PCA-5NIP obtained from complete solvent evaporation.

Fig.S14.TGAthermogramsof(a)PCA,(b)5NIP, (c) physical mixture of PCA:5NIP (1:1 mol ratio), and (d) PCA-5NIP

and (c) PCA-5NIP

Fig.S52.MeltingpointphasediagramofPCA-5NIPcocrystalsystem.

Fig. S63.Polarizedlightmicroscopy (PLM)imagesof(a)PCA,(b)5NIP,(c)physicalmixtureofPCA:5NIP(1:1molratio)afterrecrystalizedusingmethanol.

Fig.S47.Hotstagepolarizedmicroscopy (HSPM)imagesofphasetransitionduringheatingprocessfromphysicalmixture(1:1molratio)ofPCA:5NIP(a)120oC,(b)155oC,

Fig.S85.PowderX-raydiffractograms(a)PCA,(b)5NIP,(c)PCA-5NIP beforesolubilitystudy,and (d)PCA-5NIP aftersolubilitystudyinphosphatebufferpH5.8

Fig. S69.Powder X-ray diffractograms resulting from stability study under accelerated conditions (a) PCA day 0, (b) PCA day 30 in open condition, (c) PCA day 30 in close condition, (d) PCA-5NIP day 0, (e) PCA-5NIP day 30 in open condition, and

(f) PCA-5NIP day 30 in close condition