# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email scburdette@WPI.EDU _publ_contact_author_name 'Shawn Burdette' loop_ _publ_author_name 'Shawn Burdette' 'Charlene Signh' 'Tracey Friss' 'Celina Gwizdala' data_shawn004_0m _database_code_depnum_ccdc_archive 'CCDC 864178' #TrackingRef '- Shawn004_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H19 Cl2 N3 O Zn' _chemical_formula_weight 441.64 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.7523(3) _cell_length_b 25.2982(11) _cell_length_c 10.7609(4) _cell_angle_alpha 90.00 _cell_angle_beta 106.849(2) _cell_angle_gamma 90.00 _cell_volume 2019.82(14) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.452 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 904 _exptl_absorpt_coefficient_mu 1.493 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.7545 _exptl_absorpt_correction_T_max 0.9708 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _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 17291 _diffrn_reflns_av_R_equivalents 0.0361 _diffrn_reflns_av_sigmaI/netI 0.0394 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 26.19 _reflns_number_total 3997 _reflns_number_gt 2910 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0321P)^2^+0.8051P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3997 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0608 _refine_ls_R_factor_gt 0.0343 _refine_ls_wR_factor_ref 0.0756 _refine_ls_wR_factor_gt 0.0681 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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 Zn1 Zn 0.31496(4) 0.626483(12) 0.61727(3) 0.03314(10) Uani 1 1 d . . . N1 N 0.1927(3) 0.55605(8) 0.65092(19) 0.0336(5) Uani 1 1 d . . . N2 N 0.4504(3) 0.69325(8) 0.7157(2) 0.0346(5) Uani 1 1 d . . . C19 C 0.2352(4) 0.50801(11) 0.6180(3) 0.0412(7) Uani 1 1 d . . . H19 H 0.3335 0.5046 0.5825 0.049 Uiso 1 1 calc R . . C15 C 0.0543(3) 0.56119(11) 0.7016(2) 0.0349(6) Uani 1 1 d . . . C9 C 0.3635(3) 0.72222(11) 0.7834(2) 0.0345(6) Uani 1 1 d . . . C16 C -0.0434(4) 0.51796(12) 0.7197(3) 0.0482(7) Uani 1 1 d . . . H16 H -0.1402 0.5220 0.7564 0.058 Uiso 1 1 calc R . . C10 C 0.4392(4) 0.76679(12) 0.8502(3) 0.0464(7) Uani 1 1 d . . . H10 H 0.3755 0.7866 0.8978 0.056 Uiso 1 1 calc R . . C13 C 0.6141(4) 0.70930(12) 0.7140(3) 0.0431(7) Uani 1 1 d . . . H13 H 0.6758 0.6893 0.6655 0.052 Uiso 1 1 calc R . . C18 C 0.1434(4) 0.46350(12) 0.6330(3) 0.0499(8) Uani 1 1 d . . . H18 H 0.1771 0.4298 0.6089 0.060 Uiso 1 1 calc R . . C17 C 0.0013(5) 0.46872(13) 0.6839(3) 0.0565(9) Uani 1 1 d . . . H17 H -0.0660 0.4385 0.6943 0.068 Uiso 1 1 calc R . . C12 C 0.6969(4) 0.75322(12) 0.7790(3) 0.0497(8) Uani 1 1 d . . . H12 H 0.8140 0.7631 0.7764 0.060 Uiso 1 1 calc R . . C11 C 0.6078(4) 0.78259(13) 0.8477(3) 0.0524(8) Uani 1 1 d . . . H11 H 0.6617 0.8134 0.8929 0.063 Uiso 1 1 calc R . . C14 C 0.0125(3) 0.61666(10) 0.7339(2) 0.0359(6) Uani 1 1 d . . . H14A H -0.0588 0.6350 0.6543 0.043 Uiso 1 1 calc R . . H14B H -0.0591 0.6160 0.7965 0.043 Uiso 1 1 calc R . . C8 C 0.1783(3) 0.70271(10) 0.7795(3) 0.0361(6) Uani 1 1 d . . . H8A H 0.1409 0.7183 0.8520 0.043 Uiso 1 1 calc R . . H8B H 0.0899 0.7134 0.6968 0.043 Uiso 1 1 calc R . . N4 N 0.1836(3) 0.64473(8) 0.79058(19) 0.0322(5) Uani 1 1 d . . . C1 C 0.2711(3) 0.62687(11) 0.9218(2) 0.0378(6) Uani 1 1 d . . . C6 C 0.1957(4) 0.63679(12) 1.0233(3) 0.0455(7) Uani 1 1 d . . . C2 C 0.4294(4) 0.59838(12) 0.9476(3) 0.0537(8) Uani 1 1 d . . . H2 H 0.4831 0.5916 0.8802 0.064 Uiso 1 1 calc R . . C5 C 0.2795(5) 0.61885(14) 1.1467(3) 0.0607(9) Uani 1 1 d . . . H5 H 0.2293 0.6262 1.2156 0.073 Uiso 1 1 calc R . . C4 C 0.4357(5) 0.59025(16) 1.1697(4) 0.0787(12) Uani 1 1 d . . . H4 H 0.4928 0.5777 1.2549 0.094 Uiso 1 1 calc R . . C3 C 0.5103(5) 0.57957(15) 1.0726(4) 0.0751(11) Uani 1 1 d . . . H3 H 0.6178 0.5593 1.0901 0.090 Uiso 1 1 calc R . . C7 C -0.0564(5) 0.67061(18) 1.0836(4) 0.0913(14) Uani 1 1 d . . . H7A H -0.0914 0.6359 1.1089 0.137 Uiso 1 1 calc R . . H7B H -0.1646 0.6919 1.0464 0.137 Uiso 1 1 calc R . . H7C H 0.0213 0.6886 1.1602 0.137 Uiso 1 1 calc R . . O1 O 0.0385(3) 0.66395(9) 0.98985(19) 0.0596(6) Uani 1 1 d . . . Cl1 Cl 0.09130(9) 0.66432(3) 0.45323(6) 0.04294(18) Uani 1 1 d . . . Cl2 Cl 0.54220(10) 0.59284(3) 0.54751(8) 0.0549(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 Zn1 0.03179(17) 0.03425(18) 0.03475(17) -0.00113(14) 0.01180(12) 0.00203(14) N1 0.0323(12) 0.0352(13) 0.0320(12) 0.0013(10) 0.0071(9) 0.0017(10) N2 0.0306(12) 0.0385(14) 0.0375(12) -0.0036(10) 0.0142(10) 0.0010(10) C19 0.0422(16) 0.0343(17) 0.0416(16) -0.0004(13) 0.0036(13) 0.0079(14) C15 0.0334(15) 0.0389(17) 0.0288(13) 0.0028(12) 0.0034(11) -0.0038(13) C9 0.0358(15) 0.0333(15) 0.0364(14) -0.0003(12) 0.0135(12) 0.0034(12) C16 0.0487(18) 0.050(2) 0.0474(17) 0.0033(15) 0.0155(14) -0.0087(16) C10 0.0496(18) 0.0405(18) 0.0528(18) -0.0104(14) 0.0207(15) 0.0012(15) C13 0.0386(16) 0.0484(19) 0.0461(17) -0.0055(14) 0.0184(13) 0.0026(14) C18 0.057(2) 0.0343(18) 0.0480(17) 0.0043(14) -0.0011(15) 0.0042(15) C17 0.067(2) 0.040(2) 0.056(2) 0.0091(15) 0.0064(17) -0.0149(17) C12 0.0396(16) 0.051(2) 0.0611(19) -0.0071(16) 0.0191(15) -0.0095(15) C11 0.0520(19) 0.0422(19) 0.063(2) -0.0134(16) 0.0159(16) -0.0110(16) C14 0.0296(14) 0.0433(18) 0.0361(14) 0.0007(12) 0.0116(12) 0.0004(12) C8 0.0374(15) 0.0333(16) 0.0433(15) -0.0006(12) 0.0206(12) 0.0053(13) N4 0.0290(11) 0.0331(13) 0.0349(12) -0.0023(10) 0.0098(9) 0.0013(10) C1 0.0362(15) 0.0384(16) 0.0366(14) -0.0010(13) 0.0070(12) -0.0038(13) C6 0.0493(18) 0.0471(19) 0.0414(16) 0.0001(14) 0.0152(14) -0.0049(15) C2 0.0431(18) 0.059(2) 0.0526(19) 0.0055(16) 0.0033(15) 0.0062(16) C5 0.075(2) 0.067(2) 0.0388(18) 0.0019(16) 0.0145(16) -0.011(2) C4 0.075(3) 0.098(3) 0.049(2) 0.015(2) -0.004(2) 0.003(2) C3 0.058(2) 0.088(3) 0.065(2) 0.014(2) -0.0036(19) 0.018(2) C7 0.094(3) 0.129(4) 0.069(3) 0.005(2) 0.051(2) 0.021(3) O1 0.0663(15) 0.0727(16) 0.0486(12) 0.0025(11) 0.0305(11) 0.0110(12) Cl1 0.0403(4) 0.0460(4) 0.0399(4) 0.0101(3) 0.0075(3) 0.0017(3) Cl2 0.0462(4) 0.0541(5) 0.0733(5) -0.0163(4) 0.0313(4) 0.0028(4) _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 Zn1 N1 2.099(2) . ? Zn1 N2 2.105(2) . ? Zn1 Cl2 2.2712(7) . ? Zn1 Cl1 2.2943(7) . ? Zn1 N4 2.414(2) . ? N1 C19 1.334(3) . ? N1 C15 1.343(3) . ? N2 C13 1.337(3) . ? N2 C9 1.344(3) . ? C19 C18 1.367(4) . ? C15 C16 1.376(4) . ? C15 C14 1.504(4) . ? C9 C10 1.374(4) . ? C9 C8 1.507(3) . ? C16 C17 1.377(4) . ? C10 C11 1.375(4) . ? C13 C12 1.370(4) . ? C18 C17 1.371(4) . ? C12 C11 1.368(4) . ? C14 N4 1.472(3) . ? C8 N4 1.471(3) . ? N4 C1 1.450(3) . ? C1 C2 1.380(4) . ? C1 C6 1.403(4) . ? C6 O1 1.354(3) . ? C6 C5 1.375(4) . ? C2 C3 1.393(4) . ? C5 C4 1.370(5) . ? C4 C3 1.360(5) . ? C7 O1 1.420(4) . ? 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 Zn1 N2 141.14(8) . . ? N1 Zn1 Cl2 99.87(6) . . ? N2 Zn1 Cl2 98.37(6) . . ? N1 Zn1 Cl1 102.03(6) . . ? N2 Zn1 Cl1 102.00(6) . . ? Cl2 Zn1 Cl1 112.81(3) . . ? N1 Zn1 N4 73.51(8) . . ? N2 Zn1 N4 73.64(7) . . ? Cl2 Zn1 N4 150.25(5) . . ? Cl1 Zn1 N4 96.93(5) . . ? C19 N1 C15 119.0(2) . . ? C19 N1 Zn1 124.67(18) . . ? C15 N1 Zn1 116.22(18) . . ? C13 N2 C9 117.9(2) . . ? C13 N2 Zn1 124.99(18) . . ? C9 N2 Zn1 117.07(17) . . ? N1 C19 C18 122.8(3) . . ? N1 C15 C16 121.2(3) . . ? N1 C15 C14 115.8(2) . . ? C16 C15 C14 123.0(2) . . ? N2 C9 C10 121.7(2) . . ? N2 C9 C8 115.4(2) . . ? C10 C9 C8 122.9(2) . . ? C15 C16 C17 119.1(3) . . ? C9 C10 C11 119.5(3) . . ? N2 C13 C12 123.1(3) . . ? C19 C18 C17 118.3(3) . . ? C18 C17 C16 119.7(3) . . ? C11 C12 C13 118.8(3) . . ? C12 C11 C10 119.0(3) . . ? N4 C14 C15 108.5(2) . . ? N4 C8 C9 108.7(2) . . ? C1 N4 C8 112.6(2) . . ? C1 N4 C14 111.4(2) . . ? C8 N4 C14 116.5(2) . . ? C1 N4 Zn1 120.63(15) . . ? C8 N4 Zn1 97.83(14) . . ? C14 N4 Zn1 96.82(14) . . ? C2 C1 C6 118.9(3) . . ? C2 C1 N4 119.8(2) . . ? C6 C1 N4 121.3(2) . . ? O1 C6 C5 124.1(3) . . ? O1 C6 C1 115.4(2) . . ? C5 C6 C1 120.4(3) . . ? C1 C2 C3 119.8(3) . . ? C4 C5 C6 119.6(3) . . ? C3 C4 C5 121.1(3) . . ? C4 C3 C2 120.1(3) . . ? C6 O1 C7 118.9(3) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 26.19 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.569 _refine_diff_density_min -0.264 _refine_diff_density_rms 0.056