Supporting Information

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1 Electronic Supplementary Material (ESI) for CrystEngComm. This journal is The Royal Society of Chemistry 017 Supporting Information The Crystalline Sponge Method: A Solvent-Based Strategy to Facilitate Noncovalent Ordered Trapping of Solid and Liquid Organic Compounds Timothy R. Ramadhar, a, * Shao-Liang Zheng, b Yu-Sheng Chen, c and Jon Clardy a, * a Department of Biological Chemistry and Molecular Pharmacology, Harvard Medical School, 40 Longwood Avenue, Boston, Massachusetts, 0115, United States of America b Department of Chemistry and Chemical Biology, Harvard University, 1 Oxford Street, Cambridge, Massachusetts, 0138, United States of America c ChemMatCARS, Center for Advanced Radiation Sources, The University of Chicago c/o Advanced Photon Source, Argonne National Laboratory, 9700 South Cass Avenue, Argonne, Illinois, 60439, United States of America timothy_ramadhar@hms.harvard.edu; jon_clardy@hms.harvard.edu Table of contents Table S1. Crystallographic details for 1... S Table S. Crystallographic details for S3 Table S3. Crystallographic details for S4 Table S4. Crystallographic details for S5 Void Analysis... S6 S1

2 Table S1. Crystallographic details for 1 tim73-transstilbene-mtbe_a CCDC Chemical formula C 36H 4I 6N 1Zn 3.04(C 14H 1) M r Crystal system, space group Monoclinic, C/c a, b, c (Å) (14), (6), (14) ( ) (8) V (Å 3 ) (1) Z 8 (mm -1 ) 0.70 Crystal size (mm) T min, T max 0.884, 0.95 R int (sin / ) max (Å -1 ) Huber three-circle goniometer with free kappa SADABS014/5 (Bruker, 014/5) was used for absorption correction. wr (int) was before and after correction. The ratio of minimum to maximum transmission is The / correction factor is , 1544, R[F > (F )], wr(f ), S 0.05, 0.181, 1.03 No. of 1544 No. of parameters 965 No. of restraints 573 max, min (e Å -3 ) 1.97, w = 1/[ (F o ) + (0.1106P) P] + F c )/3 S

3 Table S. Crystallographic details for 1 3 tim70c-vanillin_a CCDC Chemical formula C 7H 48I 1N 4Zn 6.07(C 8H 8O 3) M r Crystal system, space group Triclinic, P 1 a, b, c (Å) (8), (11), (18),, ( ) (10), (10), (9) V (Å 3 ) (8) Z (mm -1 ) 0.7 Crystal size (mm) T min, T max 0.853, R int (sin / ) max (Å -1 ) Huber three-circle goniometer with free kappa SADABS014/5 (Bruker, 014/5) was used for absorption correction. wr (int) was before and after correction. The ratio of minimum to maximum transmission is The / correction factor is , 9411, 3438 R[F > (F )], wr(f ), S 0.07, 0.45, 1.06 No. of 9411 No. of parameters 1471 No. of restraints 39 max, min (e Å -3 ).18, -1.4 w = 1/[ (F o ) + (0.131P) P] + F c )/3 S3

4 Table S3. Crystallographic details for 1 4 znimof-cf3phenylazide_a CCDC Chemical formula C 36H 4I 6N 1Zn (C 5H 1O) 0.66(C 7H 4F 3N 3) M r Crystal system, space group Monoclinic, C/c a, b, c (Å) (17), (7), (15) ( ) (1) V (Å 3 ) (13) Z 8 (mm -1 ) 0.75 Crystal size (mm) Bruker D8 goniometer T min, T max 0.88, R int (sin / ) max (Å -1 ) SADABS014/5 (Bruker, 014/5) was used for absorption correction. wr (int) was before and after correction. The ratio of minimum to maximum transmission is The / correction factor is , 14007, 1174 R[F > (F )], wr(f ), S 0.058, 0.7, 1.16 No. of No. of parameters 711 No. of restraints 73 max, min (e Å -3 ).61, -.10 w = 1/[ (F o ) + (0.1337P) P] + F c )/3 S4

5 Table S4. Crystallographic details for 1 5 tim83-artemisinin-c_c CCDC Chemical formula C 7H 48I 1N 4Zn (C 15H O 5) 0.6(C 5H 1O) M r Crystal system, space group Monoclinic, C a, b, c (Å) 35.5 (), (8), () ( ) (11) V (Å 3 ) (17) Z 4 (mm -1 ) 0.68 Crystal size (mm) T min, T max 0.8, R int (sin / ) max (Å -1 ) Huber three-circle goniometer with free kappa SADABS014/5 (Bruker, 014/5) was used for absorption correction. wr(int) was before and after correction. The ratio of minimum to maximum transmission is The / correction factor is , 30760, 5384 R[F > (F )], wr(f ), S 0.070, 0.34, 1.07 No. of No. of parameters 1310 No. of restraints 156 max, min (e Å -3 ).6, -1. Absolute structure w = 1/[ (F o ) + (0.1379P) P] + F c )/3 Flack x determined using 109 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (013) 49-59). Hooft y (Hooft, Straver and Spek, J. Appl. Cryst. (008) ). A three-hypothesis model based on Bayesian statistical analysis on Bijvoet pairs using a Student's t- distribution was employed to determine absolute configuration. p3(true) = 1.000, p3(false) = 0.0E+00, p3(rac-twin) = 0.3E-37 Absolute structure parameter Flack x: 0.18(3); Hooft y: 0.15(); p3(true) = 1.000, p3(false) = 0.0E+00, p3(rac-twin) = 0.3E-37 S5

6 Void Analysis Void volume and total void percentage (relative to unit cell volume) for the soaked crystalline sponges were determined using PLATON/SQUEEZE (A. L. Spek, Acta Crystallogr., Sect. C.: Struct. Chem., 015, 71, 9) (note: all structures reported in this article are UNSQUEEZED and have not been treated with other residual electron density attenuation programs). 1 : Void Volume: 987 Å 3, Void Percentage: 17% 1 3: Void Volume: 590 Å 3, Void Percentage: 31% 1 4: Void Volume: 440 Å 3, Void Percentage: 8% 1 5: Void Volume: 7300 Å 3, Void Percentage: 4% S6