<p> Supporting Information for</p><p>Hydrogen bond induced chiral symmetry breaking in the crystallization of nickel(II) complexes</p><p>Guang-Chuan Ou a, b Zhi-Zhang Li a Lin Yuan a, b Xian-You Yuan a a Department of Biology and Chemistry, Hunan University of Science and Engineering, 425199 Yongzhou, Hunan, P. R. China b Key Laboratory of Functional Organometallic Materials of Hunan Province College, Hengyang Normal University, 421008 Hengyang, Hunan, P. R. China</p><p>*Corresponding author OU Guang-Chuan email: [email protected]； YUAN Xian-You email: [email protected]</p><p>S1 Table S1. The crystallographic data of complexes</p><p>Number 1 2 3 4 5 6</p><p>Empirical formula C6H19N4NiClO6 C6H19N4NiClO6 C6H19N4NiClO6 C6H19N4NiClO6 C6H19N4NiClO6 C6H19N4NiClO6 Formula weight 337.41 337.41 337.41 337.41 337.41 337.41 Temperature (K) 296(2) 296(2) 296(2) 296(2) 296(2) 296(2) Crystal system Tetragonal Tetragonal Tetragonal Tetragonal Tetragonal Tetragonal Space group P41212 P41212 P43212 P43212 P43212 P43212 a / Å 9.5267(9) 9.5611(4) 9.5612(3) 9.5627(4) 9.5807(14) 9.5579(3) b / Å 9.5267(9) 9.5611(4) 9.5612(3) 9.5627(4) 9.5807(14) 9.5579(3) c / Å 30.465(6) 30.432(4) 30.4175(17) 30.448(3) 30.497(10) 30.4349(16) V /Å 3 2764.9(6) 2781.9(4) 2780.7(2) 2784.3(4) 2799.4(10) 2780.33(19) Z 8 8 8 8 8 8 -3 Dc/g cm 1.621 1.611 1.612 1.610 1.601 1.612 μ / mm-1 1.621 1.611 1.612 1.610 1.601 1.612 F(000) 1408 1408 1408 1408 1408 1408 Crystal size (mm) 0.46  0.42  0.36 0.42  0.39  0.31 0.45  0.41  0.35 0.44  0.38  0.31 0.45  0.40  0.32 0.42 0.39  0.32 θ range for data 2.24−27.70 2.23−27.48 2.23−27.50 2.93−27.52 2.23−27.33 2.23−27.48 collection Reflections 9946/3215 15505/3140 12002/3183 10062/3148 11563/3060 22958/3209 collected /unique refl. (0.0392) (0.0830) (0.0229) (0.0549) (0.0295) (0.0274) (Rint) 99.2 98.4 99.7 97.8 98.0 99.8 Completeness to θ 1.077 1.074 1.078 1.084 1.086 1.059 S on F2 0.0645, 0.1857 0.0726, 0.2079 0.0560, 0.1598 0.0927, 0.2653 0.0690, 0.2059 0.0550, 0.1641 R indices (I>2σ (I)) 0.0700, 0.1971 0.0944, 0.2301 0.0643, 0.1730 0.1018, 0.2730 0.0746, 0.2133 0.0605, 0.1749 R indices (all data) 0.08(4) 0.06(5) 0.04(3) 0.06(6) 0.08(5) 0.04(4) Abs. struct. Parameter 0.739/−0.855 0.733/−0.782 1.157/−1.192 1.132/−0.892 1.106/−0.657 0.867/−0.655 Max. peak/hole(e. Å−3)</p><p>S2 S3</p>