Validation of a search technique for crystal structure prediction of

Supplementary Information Conformer label

3a 3a 3b 3b 3c 3c 3d 3d 10g 10g 3a 10g 3e 3c 3e 3c 3b 3b 3a 3b 3d 10g 3f 3d 10d 3e 3f 10d 10b 10d 10g 3e 3f 1d 10b 3g 1c 4b 1d 3c 1c 3g 2a 2a 1c 3g 2c 10h 4a 6f 10h 3a 9o

θ1 / ˚

88 88 90 90 90 90 90 90 80 80 88 80 90 90 90 90 90 90 88 90 90 80 90 90 100 90 90 100 120 100 80 90 90 69 120 90 87 90 69 90 87 90 100 100 87 90 80 120 90 120 120 88 120

θ2 / ˚

160 160 160 160 160 160 160 160 160 160 160 160 160 160 160 160 160 160 160 160 160 160 160 160 160 160 160 160 -34 160 160 160 160 -160 -34 160 160 160 -160 160 160 160 160 160 160 160 160 -20 160 -36 -20 160 160

Energy / kJmol-1 ∆Eintra

Ulatt

Etot

13.05 13.05 13.07 13.07 13.30 13.30 12.81 12.81 13.57 13.57 13.05 13.57 12.53 13.30 12.53 13.30 13.07 13.07 13.05 13.07 12.81 13.57 12.27 12.81 13.71 12.53 12.27 13.71 12.55 13.71 13.57 12.53 12.27 10.81 12.55 12.10 12.04 19.35 10.81 13.30 12.04 12.10 12.84 12.84 12.04 12.10 12.37 13.80 20.37 12.01 13.80 13.05 15.77

-108.95 -108.90 -108.81 -108.79 -108.94 -108.88 -108.35 -108.30 -109.03 -108.93 -108.16 -108.66 -107.52 -108.23 -107.36 -108.12 -107.85 -107.85 -107.75 -107.70 -107.27 -107.86 -106.37 -106.87 -107.70 -106.37 -106.01 -107.36 -106.10 -107.08 -106.73 -105.63 -105.26 -103.16 -104.90 -104.40 -104.19 -111.44 -102.75 -105.21 -103.88 -103.88 -104.54 -104.54 -103.68 -103.72 -103.83 -105.23 -111.79 -103.35 -105.12 -104.31 -106.89

-95.90 -95.84 -95.74 -95.72 -95.64 -95.58 -95.53 -95.49 -95.46 -95.37 -95.11 -95.09 -94.99 -94.93 -94.83 -94.83 -94.78 -94.77 -94.70 -94.63 -94.46 -94.29 -94.10 -94.06 -93.99 -93.84 -93.74 -93.65 -93.56 -93.37 -93.16 -93.10 -92.99 -92.35 -92.35 -92.30 -92.16 -92.09 -91.94 -91.91 -91.84 -91.78 -91.71 -91.70 -91.64 -91.63 -91.46 -91.43 -91.42 -91.34 -91.32 -91.25 -91.12

Volume per molecule / Å3 173.93 173.21 173.36 174.44 173.7 174.76 173.13 174.18 172.58 172.91 172.32 171.5 172.99 175.49 174.03 173.09 172.69 172.69 175.1 175.34 172.4 173.83 173 175.25 174.51 172.27 174.03 175.66 174.6 175.88 175.38 175.28 172.47 176.03 179.3 173.2 173.02 173.16 179.07 178.81 172.2 173.04 173.87 173.75 173.95 174.21 170.69 176.83 172.35 175.48 173.74 178.04 174.39

Space group

Packing Motif

P21/c P21/c P21/c P21/c P21/c P21/c P21/c P21/c P21/c P21/c P-1 P-1 P21/c P-1 P21/c P-1 P-1 P-1 P-1 P-1 P-1 P-1 P21/c P-1 P21/c P-1 P21/c P21/c P21/c P-1 P21/c P-1 P-1 P-1 P-1 P21/c P21/c P-1 P21/c P21/c P-1 P-1 P21/c P-1 P21/c P21/c P-1 P-1 P-1 P21/c P21/c P21/c P21/c

III 1 1 III 1 III 1 III III 1 2 2 1 II III 2 2 2 II II 2 II 1 II 1 2 III III IV II 3 II 2 4 5 1 1 II 6 7 2 2 1 2 III III 2 5 II IV IV 7 8

10b 3b 1a 4c 10a 1e

120 90 68 90 74 96

-34 160 -150 160 -150 140

12.55 13.07 11.18 19.27 14.36 16.24

-103.66 -104.17 -102.27 -110.36 -105.40 -107.14

-91.11 -91.10 -91.09 -91.09 -91.05 -90.91

182.41 178.54 179.02 173.86 176.48 175.01

C2/c P21/c P21/c P-1 P-1 P21/c

Crystal structures in the lowest 5kJmol-1 of Etot; the six structures in bold were suggested (in the order they appear here) as predictions of form IV.

9 7 10 II 4 1