# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Chemical Science' _journal_coden_cambridge 1475 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email dudy540@163.com _publ_contact_author_name 'Jun-Sheng Qin' loop_ _publ_author_name 'Zhong-Min Su' 'Ya-Qian Lan' 'Jun-Sheng Qin' data_mm _database_code_depnum_ccdc_archive 'CCDC 843864' #TrackingRef 'mm.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H10 N12 O Zn' _chemical_formula_sum 'C8 H10 N12 O Zn' _chemical_formula_weight 355.65 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Trigonal _symmetry_space_group_name_H-M R-3 _symmetry_space_group_name_Hall -R3 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 23.8620(19) _cell_length_b 23.8620(19) _cell_length_c 14.6860(19) _cell_angle_alpha 90.000(2) _cell_angle_beta 90.000(2) _cell_angle_gamma 120.000(2) _cell_volume 7241.8(12) _cell_formula_units_Z 18 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.468 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3240 _exptl_absorpt_coefficient_mu 1.547 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7575 _exptl_absorpt_correction_T_max 0.8125 _exptl_absorpt_process_details 'SADABS(Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12293 _diffrn_reflns_av_R_equivalents 0.0322 _diffrn_reflns_av_sigmaI/netI 0.0269 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.70 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2844 _reflns_number_gt 2339 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SMART (Bruker, 1997)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97(Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (Sheldrick, 1990)' _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0995P)^2^+20.0040P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2844 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0509 _refine_ls_R_factor_gt 0.0403 _refine_ls_wR_factor_ref 0.1462 _refine_ls_wR_factor_gt 0.1377 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons 1 0.000 0.000 -0.009 463.7 100.7 2 0.333 0.667 0.060 475.3 100.6 3 0.667 0.333 -0.086 475.3 100.6 _platon_squeeze_details ; ? ; loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.28892(18) 0.07784(17) 0.6606(2) 0.0304(8) Uani 1 1 d . . . C2 C 0.25469(18) 0.10492(17) 0.6212(2) 0.0301(8) Uani 1 1 d . . . C3 C 0.32634(18) 0.05083(17) 0.6216(2) 0.0303(8) Uani 1 1 d . . . C4 C 0.24325(17) 0.11493(17) 0.5268(3) 0.0303(8) Uani 1 1 d . . . C5 C 0.4983(13) 0.1896(14) 0.2679(10) 0.376(19) Uani 1 1 d . . . H5A H 0.5161 0.1909 0.2087 0.565 Uiso 1 1 calc R . . H5B H 0.4769 0.1459 0.2902 0.565 Uiso 1 1 calc R . . H5C H 0.5325 0.2169 0.3089 0.565 Uiso 1 1 calc R . . C6 C 0.4399(8) 0.2293(8) 0.1722(6) 0.232(8) Uani 1 1 d . . . H6A H 0.4656 0.2237 0.1269 0.348 Uiso 1 1 calc R . . H6B H 0.4503 0.2737 0.1731 0.348 Uiso 1 1 calc R . . H6C H 0.3949 0.2021 0.1580 0.348 Uiso 1 1 calc R . . C7 C 0.4279(5) 0.2132(4) 0.3354(4) 0.103(3) Uani 1 1 d . . . C8 C 0.3803(6) 0.2364(9) 0.3307(8) 0.206(7) Uani 1 1 d . . . H8A H 0.3737 0.2436 0.2683 0.310 Uiso 1 1 calc R . . H8B H 0.3967 0.2762 0.3641 0.310 Uiso 1 1 calc R . . H8C H 0.3399 0.2045 0.3568 0.310 Uiso 1 1 calc R . . N1 N 0.28762(18) 0.08353(17) 0.7506(2) 0.0407(8) Uani 1 1 d . . . N2 N 0.25280(18) 0.11260(17) 0.7625(2) 0.0444(9) Uani 1 1 d . . . H2 H 0.2443 0.1214 0.8157 0.053 Uiso 1 1 calc R . . N3 N 0.23244(17) 0.12683(16) 0.6879(2) 0.0390(8) Uani 1 1 d . . . N4 N 0.23559(16) 0.16379(15) 0.4990(2) 0.0345(7) Uani 1 1 d . . . N5 N 0.2231(2) 0.15488(18) 0.4087(2) 0.0489(9) Uani 1 1 d . . . N6 N 0.2238(2) 0.10339(19) 0.3831(2) 0.0488(10) Uani 1 1 d . . . N7 N 0.23693(16) 0.07716(15) 0.4561(2) 0.0351(8) Uani 1 1 d . . . N8 N 0.37688(16) 0.05253(16) 0.6619(2) 0.0344(7) Uani 1 1 d . . . N9 N 0.39841(18) 0.02334(19) 0.6048(3) 0.0469(9) Uani 1 1 d . . . N10 N 0.36243(18) 0.00454(19) 0.5329(3) 0.0473(9) Uani 1 1 d . . . N11 N 0.31598(15) 0.02162(16) 0.5414(2) 0.0346(7) Uani 1 1 d . . . N12 N 0.4534(6) 0.2116(5) 0.2616(4) 0.153(4) Uani 1 1 d . . . O1 O 0.4436(4) 0.1991(3) 0.4097(3) 0.123(2) Uani 1 1 d . . . Zn1 Zn 0.24606(2) -0.00218(2) 0.44746(3) 0.0306(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.035(2) 0.0255(18) 0.0256(18) -0.0018(14) -0.0033(15) 0.0118(16) C2 0.035(2) 0.0248(18) 0.0277(19) -0.0010(14) 0.0014(15) 0.0127(16) C3 0.0329(19) 0.0269(18) 0.0267(19) 0.0021(14) -0.0037(15) 0.0116(16) C4 0.0310(19) 0.0302(19) 0.0283(19) -0.0011(15) -0.0020(15) 0.0142(16) C5 0.70(4) 0.69(5) 0.144(13) 0.104(19) 0.13(2) 0.65(4) C6 0.34(2) 0.37(2) 0.042(5) 0.030(9) 0.007(8) 0.214(19) C7 0.157(8) 0.098(5) 0.042(4) 0.001(3) 0.011(4) 0.053(5) C8 0.146(10) 0.42(2) 0.113(8) 0.050(11) 0.018(7) 0.185(14) N1 0.053(2) 0.0411(19) 0.0250(17) 0.0037(14) 0.0010(15) 0.0217(17) N2 0.062(2) 0.048(2) 0.0255(17) -0.0002(15) 0.0075(16) 0.0293(19) N3 0.047(2) 0.0383(18) 0.0327(18) 0.0012(14) 0.0050(15) 0.0226(16) N4 0.047(2) 0.0353(17) 0.0279(17) -0.0027(13) -0.0076(14) 0.0259(16) N5 0.074(3) 0.048(2) 0.0337(19) -0.0044(16) -0.0149(18) 0.037(2) N6 0.073(3) 0.053(2) 0.0301(19) -0.0091(16) -0.0166(17) 0.039(2) N7 0.048(2) 0.0331(17) 0.0257(16) -0.0030(13) -0.0039(14) 0.0217(16) N8 0.0400(18) 0.0374(18) 0.0294(17) -0.0026(14) -0.0061(14) 0.0220(15) N9 0.048(2) 0.056(2) 0.046(2) -0.0126(17) -0.0085(17) 0.0328(19) N10 0.048(2) 0.059(2) 0.043(2) -0.0163(18) -0.0092(17) 0.0326(19) N11 0.0342(17) 0.0394(18) 0.0294(17) -0.0065(14) -0.0051(13) 0.0178(15) N12 0.295(12) 0.191(8) 0.047(4) 0.011(4) 0.023(5) 0.177(9) O1 0.245(7) 0.138(4) 0.038(2) 0.006(2) 0.023(3) 0.135(5) Zn1 0.0346(3) 0.0286(3) 0.0243(3) -0.00474(16) -0.00097(16) 0.0126(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.331(5) . ? C1 C2 1.396(5) . ? C1 C3 1.454(5) . ? C2 N3 1.340(5) . ? C2 C4 1.455(5) . ? C3 N8 1.326(5) . ? C3 N11 1.327(5) . ? C4 N4 1.331(5) . ? C4 N7 1.333(5) . ? C5 N12 1.414(14) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 N12 1.463(12) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 N12 1.252(9) . ? C7 O1 1.254(8) . ? C7 C8 1.494(12) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? N1 N2 1.334(5) . ? N2 N3 1.310(5) . ? N2 H2 0.8600 . ? N4 N5 1.353(5) . ? N4 Zn1 1.993(3) 12_556 ? N5 N6 1.294(5) . ? N6 N7 1.355(5) . ? N7 Zn1 2.015(3) . ? N8 N9 1.346(5) . ? N8 Zn1 1.974(3) 6 ? N9 N10 1.291(5) . ? N10 N11 1.365(5) . ? N11 Zn1 2.016(3) . ? Zn1 N8 1.974(3) 8_544 ? Zn1 N4 1.993(3) 11_556 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 108.4(3) . . ? N1 C1 C3 119.1(3) . . ? C2 C1 C3 132.3(3) . . ? N3 C2 C1 108.3(3) . . ? N3 C2 C4 119.3(3) . . ? C1 C2 C4 132.3(3) . . ? N8 C3 N11 109.9(3) . . ? N8 C3 C1 124.1(3) . . ? N11 C3 C1 126.0(3) . . ? N4 C4 N7 109.5(3) . . ? N4 C4 C2 123.7(3) . . ? N7 C4 C2 126.7(3) . . ? N12 C5 H5A 109.5 . . ? N12 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N12 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N12 C6 H6A 109.5 . . ? N12 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N12 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N12 C7 O1 122.0(10) . . ? N12 C7 C8 116.3(8) . . ? O1 C7 C8 121.6(7) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C1 N1 N2 103.6(3) . . ? N3 N2 N1 115.7(3) . . ? N3 N2 H2 122.2 . . ? N1 N2 H2 122.2 . . ? N2 N3 C2 103.9(3) . . ? C4 N4 N5 106.2(3) . . ? C4 N4 Zn1 136.2(3) . 12_556 ? N5 N4 Zn1 117.0(2) . 12_556 ? N6 N5 N4 109.1(3) . . ? N5 N6 N7 109.0(3) . . ? C4 N7 N6 106.1(3) . . ? C4 N7 Zn1 131.0(3) . . ? N6 N7 Zn1 122.9(2) . . ? C3 N8 N9 106.4(3) . . ? C3 N8 Zn1 131.8(3) . 6 ? N9 N8 Zn1 121.8(2) . 6 ? N10 N9 N8 109.3(3) . . ? N9 N10 N11 108.6(3) . . ? C3 N11 N10 105.8(3) . . ? C3 N11 Zn1 131.8(3) . . ? N10 N11 Zn1 122.3(3) . . ? C7 N12 C5 115.2(9) . . ? C7 N12 C6 126.0(10) . . ? C5 N12 C6 118.9(10) . . ? N8 Zn1 N4 124.04(13) 8_544 11_556 ? N8 Zn1 N7 112.35(13) 8_544 . ? N4 Zn1 N7 103.54(14) 11_556 . ? N8 Zn1 N11 107.83(13) 8_544 . ? N4 Zn1 N11 107.21(13) 11_556 . ? N7 Zn1 N11 98.94(13) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.007 _refine_diff_density_min -0.466 _refine_diff_density_rms 0.137