# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _publ_contact_author_email ghoshp_chem@yahoo.co.in _publ_contact_author_name 'Prasanta Ghosh' loop_ _publ_author_name 'Amit Saha Roy' 'Pinaki Saha' 'Partha Mitra' 'Shyam Sundar Maity' 'Sanjib Ghosh' 'Prasanta Ghosh' data_1c_CCDC_753978 _database_code_depnum_ccdc_archive 'CCDC 753978' #TrackingRef 'CCDC 753978.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H18 Br2 N2 Zn' _chemical_formula_weight 463.51 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting MONOCLINIC _symmetry_space_group_name_H-M P2(1)/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' _cell_length_a 9.2536(10) _cell_length_b 7.6218(11) _cell_length_c 12.3750(11) _cell_angle_alpha 90.00 _cell_angle_beta 97.059(2) _cell_angle_gamma 90.00 _cell_volume 866.18(17) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 6076 _cell_measurement_theta_min 1.66 _cell_measurement_theta_max 25.0 _exptl_crystal_description 'opaque rectangle' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.06 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.777 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 456 _exptl_absorpt_coefficient_mu 6.025 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.860 _exptl_absorpt_correction_T_max 0.938 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10081 _diffrn_reflns_av_R_equivalents 0.0477 _diffrn_reflns_av_sigmaI/netI 0.0291 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1645 _reflns_number_gt 1534 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0406P)^2^+0.6791P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1645 _refine_ls_number_parameters 167 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0306 _refine_ls_R_factor_gt 0.0281 _refine_ls_wR_factor_ref 0.0738 _refine_ls_wR_factor_gt 0.0726 _refine_ls_goodness_of_fit_ref 1.133 _refine_ls_restrained_S_all 1.133 _refine_ls_shift/su_max 0.000 _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 0.75190(5) 0.2500 0.09782(3) 0.01940(15) Uani 1 2 d S . . Br1 Br 0.85029(3) -0.01345(4) 0.16690(3) 0.03111(14) Uani 1 1 d . . . N1 N 0.7117(4) 0.2500 -0.0680(3) 0.0211(7) Uani 1 2 d S . . C2 C 0.5689(4) 0.2500 -0.1040(3) 0.0228(9) Uani 1 2 d S . . C3 C 0.5196(5) 0.2500 -0.2141(4) 0.0378(13) Uani 1 2 d S . . C4 C 0.6211(5) 0.2500 -0.2867(4) 0.0418(14) Uani 1 2 d S . . C5 C 0.7659(5) 0.2500 -0.2505(4) 0.0394(12) Uani 1 2 d S . . C6 C 0.8084(5) 0.2500 -0.1390(4) 0.0296(10) Uani 1 2 d S . . C7 C 0.4711(5) 0.2500 -0.0198(3) 0.0230(9) Uani 1 2 d S . . N8 N 0.5253(3) 0.2500 0.0799(3) 0.0183(7) Uani 1 2 d S . . C9 C 0.4395(4) 0.2500 0.1679(3) 0.0196(8) Uani 1 2 d S . . C10 C 0.2892(5) 0.2500 0.1566(3) 0.0287(10) Uani 1 2 d S . . C11 C 0.2166(5) 0.2500 0.2486(4) 0.0325(11) Uani 1 2 d S . . C12 C 0.2914(4) 0.2500 0.3525(3) 0.0232(9) Uani 1 2 d S . . C13 C 0.4423(5) 0.2500 0.3619(3) 0.0290(10) Uani 1 2 d S . . C14 C 0.5165(5) 0.2500 0.2717(3) 0.0265(10) Uani 1 2 d S . . C15 C 0.2158(5) 0.2500 0.4563(3) 0.0327(11) Uani 1 2 d S . . C16 C 0.0506(5) 0.2500 0.4304(4) 0.0491(16) Uani 1 2 d S . . C17 C 0.2619(4) 0.0865(6) 0.5230(3) 0.0405(9) Uani 1 1 d . . . H3 H 0.429(6) 0.2500 -0.230(4) 0.030(13) Uiso 1 2 d S . . H4 H 0.591(6) 0.2500 -0.347(5) 0.043(16) Uiso 1 2 d S . . H5 H 0.848(5) 0.2500 -0.299(4) 0.034(13) Uiso 1 2 d S . . H6 H 0.910(6) 0.2500 -0.108(4) 0.032(13) Uiso 1 2 d S . . H7 H 0.377(6) 0.2500 -0.042(4) 0.039(14) Uiso 1 2 d S . . H10 H 0.230(5) 0.2500 0.086(4) 0.034(13) Uiso 1 2 d S . . H11 H 0.119(6) 0.2500 0.245(4) 0.029(13) Uiso 1 2 d S . . H13 H 0.508(5) 0.2500 0.445(4) 0.035(13) Uiso 1 2 d S . . H14 H 0.616(6) 0.2500 0.281(4) 0.030(12) Uiso 1 2 d S . . H16A H 0.014(4) 0.143(5) 0.385(3) 0.046(11) Uiso 1 1 d . . . H16B H 0.019(5) 0.2500 0.499(4) 0.037(14) Uiso 1 2 d S . . H17A H 0.215(4) 0.076(5) 0.588(3) 0.042(10) Uiso 1 1 d . . . H17B H 0.229(4) -0.011(5) 0.480(3) 0.026(9) Uiso 1 1 d . . . H17C H 0.363(5) 0.090(5) 0.543(3) 0.046(11) Uiso 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 0.0135(2) 0.0263(3) 0.0178(2) 0.000 -0.00039(17) 0.000 Br1 0.0266(2) 0.0265(2) 0.0393(2) 0.00514(12) -0.00002(14) 0.00357(12) N1 0.0160(16) 0.0261(19) 0.0215(16) 0.000 0.0030(13) 0.000 C2 0.018(2) 0.029(2) 0.022(2) 0.000 0.0022(16) 0.000 C3 0.019(2) 0.070(4) 0.023(2) 0.000 -0.0003(18) 0.000 C4 0.033(3) 0.079(4) 0.013(2) 0.000 0.0006(19) 0.000 C5 0.031(3) 0.065(4) 0.023(2) 0.000 0.0078(19) 0.000 C6 0.016(2) 0.045(3) 0.028(2) 0.000 0.0031(17) 0.000 C7 0.016(2) 0.033(2) 0.020(2) 0.000 0.0013(16) 0.000 N8 0.0132(16) 0.0226(18) 0.0192(16) 0.000 0.0024(13) 0.000 C9 0.019(2) 0.023(2) 0.0167(18) 0.000 0.0031(15) 0.000 C10 0.019(2) 0.051(3) 0.0155(19) 0.000 -0.0018(16) 0.000 C11 0.016(2) 0.057(3) 0.025(2) 0.000 0.0040(17) 0.000 C12 0.019(2) 0.032(2) 0.0198(19) 0.000 0.0037(16) 0.000 C13 0.020(2) 0.048(3) 0.018(2) 0.000 -0.0012(16) 0.000 C14 0.013(2) 0.046(3) 0.020(2) 0.000 0.0000(16) 0.000 C15 0.023(2) 0.057(3) 0.019(2) 0.000 0.0056(17) 0.000 C16 0.023(3) 0.103(5) 0.023(2) 0.000 0.010(2) 0.000 C17 0.037(2) 0.059(3) 0.0266(17) 0.0068(18) 0.0095(15) -0.0062(19) _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 2.040(3) . ? Zn1 N8 2.082(3) . ? Zn1 Br1 2.3238(4) 4_565 ? Zn1 Br1 2.3238(4) . ? N1 C6 1.329(5) . ? N1 C2 1.341(5) . ? C2 C3 1.383(6) . ? C2 C7 1.462(5) . ? C3 C4 1.377(7) . ? C4 C5 1.360(7) . ? C5 C6 1.387(6) . ? C7 N8 1.273(5) . ? N8 C9 1.424(5) . ? C9 C10 1.381(6) . ? C9 C14 1.390(6) . ? C10 C11 1.391(6) . ? C11 C12 1.384(6) . ? C12 C13 1.387(6) . ? C12 C15 1.536(5) . ? C13 C14 1.380(6) . ? C15 C16 1.523(7) . ? C15 C17 1.526(5) 4_565 ? C15 C17 1.526(5) . ? 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 N8 80.58(13) . . ? N1 Zn1 Br1 112.63(3) . 4_565 ? N8 Zn1 Br1 112.53(3) . 4_565 ? N1 Zn1 Br1 112.63(3) . . ? N8 Zn1 Br1 112.53(3) . . ? Br1 Zn1 Br1 119.55(2) 4_565 . ? C6 N1 C2 119.7(4) . . ? C6 N1 Zn1 127.7(3) . . ? C2 N1 Zn1 112.6(3) . . ? N1 C2 C3 121.3(4) . . ? N1 C2 C7 115.7(4) . . ? C3 C2 C7 123.0(4) . . ? C4 C3 C2 118.3(4) . . ? C5 C4 C3 120.6(4) . . ? C4 C5 C6 118.4(4) . . ? N1 C6 C5 121.8(4) . . ? N8 C7 C2 119.1(4) . . ? C7 N8 C9 123.4(3) . . ? C7 N8 Zn1 112.0(3) . . ? C9 N8 Zn1 124.6(2) . . ? C10 C9 C14 119.3(4) . . ? C10 C9 N8 124.8(4) . . ? C14 C9 N8 115.9(3) . . ? C9 C10 C11 119.9(4) . . ? C12 C11 C10 121.6(4) . . ? C13 C12 C11 117.4(4) . . ? C13 C12 C15 119.2(4) . . ? C11 C12 C15 123.4(4) . . ? C14 C13 C12 121.9(4) . . ? C13 C14 C9 119.8(4) . . ? C16 C15 C17 108.7(3) . 4_565 ? C16 C15 C17 108.7(3) . . ? C17 C15 C17 109.5(4) 4_565 . ? C16 C15 C12 111.8(4) . . ? C17 C15 C12 109.0(2) 4_565 . ? C17 C15 C12 109.0(2) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.549 _refine_diff_density_min -0.898 _refine_diff_density_rms 0.105 #====END data_2 _database_code_depnum_ccdc_archive 'CCDC 813732' #TrackingRef 'CCDC 753978.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H14 Br2 N2 Zn' _chemical_formula_weight 435.46 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 14.411(2) _cell_length_b 8.4524(14) _cell_length_c 13.411(2) _cell_angle_alpha 90.00 _cell_angle_beta 105.942(5) _cell_angle_gamma 90.00 _cell_volume 1570.7(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3361 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 25.01 _exptl_crystal_description 'opaque rectangle' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.841 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 6.639 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.730 _exptl_absorpt_correction_T_max 0.873 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12779 _diffrn_reflns_av_R_equivalents 0.1045 _diffrn_reflns_av_sigmaI/netI 0.1036 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.47 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2715 _reflns_number_gt 1773 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.2000P)^2^+0.0000P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2715 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1310 _refine_ls_R_factor_gt 0.0971 _refine_ls_wR_factor_ref 0.3119 _refine_ls_wR_factor_gt 0.2765 _refine_ls_goodness_of_fit_ref 1.103 _refine_ls_restrained_S_all 1.103 _refine_ls_shift/su_max 0.000 _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 0.19859(10) 0.87482(13) 0.03064(11) 0.0427(5) Uani 1 1 d . . . Br1 Br 0.18446(11) 0.88272(15) 0.20062(11) 0.0631(6) Uani 1 1 d . . . Br2 Br 0.21348(12) 1.11390(14) -0.04993(14) 0.0696(6) Uani 1 1 d . . . N1 N 0.0877(7) 0.7433(10) -0.0599(7) 0.042(2) Uani 1 1 d . . . N8 N 0.2752(7) 0.6699(10) 0.0177(7) 0.041(2) Uani 1 1 d . . . C2 C 0.1141(8) 0.5937(12) -0.0734(8) 0.037(2) Uani 1 1 d . . . C3 C 0.0476(10) 0.4807(15) -0.1260(9) 0.052(3) Uani 1 1 d . . . H3A H 0.0664 0.3765 -0.1314 0.062 Uiso 1 1 calc R . . C4 C -0.0439(9) 0.5261(15) -0.1686(10) 0.057(3) Uani 1 1 d . . . H4A H -0.0893 0.4536 -0.2050 0.069 Uiso 1 1 calc R . . C5 C -0.0699(9) 0.6766(16) -0.1587(10) 0.055(3) Uani 1 1 d . . . H5A H -0.1331 0.7084 -0.1896 0.066 Uiso 1 1 calc R . . C6 C -0.0031(8) 0.7861(15) -0.1022(9) 0.049(3) Uani 1 1 d . . . H6A H -0.0224 0.8892 -0.0943 0.059 Uiso 1 1 calc R . . C7 C 0.2171(8) 0.5607(13) -0.0286(9) 0.040(3) Uani 1 1 d . . . H7A H 0.2407 0.4595 -0.0339 0.048 Uiso 1 1 calc R . . C9 C 0.3739(9) 0.6367(12) 0.0656(8) 0.042(3) Uani 1 1 d . . . C10 C 0.4021(9) 0.5357(13) 0.1514(9) 0.050(3) Uani 1 1 d . . . C11 C 0.4964(10) 0.5118(14) 0.1983(10) 0.058(4) Uani 1 1 d . . . H11A H 0.5148 0.4456 0.2557 0.070 Uiso 1 1 calc R . . C12 C 0.5649(9) 0.5847(18) 0.1617(11) 0.061(4) Uani 1 1 d . . . H12A H 0.6297 0.5668 0.1949 0.074 Uiso 1 1 calc R . . C13 C 0.5407(9) 0.6845(16) 0.0763(13) 0.063(4) Uani 1 1 d . . . H13A H 0.5890 0.7317 0.0527 0.076 Uiso 1 1 calc R . . C14 C 0.4443(9) 0.7141(13) 0.0261(10) 0.049(3) Uani 1 1 d . . . C15 C 0.4138(11) 0.8173(16) -0.0680(11) 0.065(4) Uani 1 1 d . . . H15A H 0.4699 0.8597 -0.0838 0.097 Uiso 1 1 calc R . . H15B H 0.3746 0.9025 -0.0549 0.097 Uiso 1 1 calc R . . H15C H 0.3772 0.7559 -0.1257 0.097 Uiso 1 1 calc R . . C16 C 0.3239(11) 0.4532(17) 0.1923(11) 0.070(4) Uani 1 1 d . . . H16A H 0.3545 0.3884 0.2510 0.106 Uiso 1 1 calc R . . H16B H 0.2842 0.3883 0.1386 0.106 Uiso 1 1 calc R . . H16C H 0.2847 0.5317 0.2129 0.106 Uiso 1 1 calc R . . 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 0.0414(9) 0.0285(8) 0.0514(9) -0.0041(5) 0.0016(6) 0.0019(5) Br1 0.0707(11) 0.0640(10) 0.0502(9) -0.0077(6) 0.0094(7) 0.0069(6) Br2 0.0773(12) 0.0315(8) 0.0972(13) 0.0090(6) 0.0193(9) 0.0019(6) N1 0.048(6) 0.037(5) 0.042(5) 0.003(4) 0.010(4) 0.002(4) N8 0.058(6) 0.026(4) 0.040(5) 0.000(4) 0.014(5) 0.000(4) C2 0.032(6) 0.038(6) 0.035(6) 0.003(4) 0.000(5) -0.006(4) C3 0.060(8) 0.044(7) 0.048(7) -0.013(5) 0.008(6) -0.014(6) C4 0.038(7) 0.055(8) 0.064(8) -0.004(6) -0.011(6) -0.012(6) C5 0.029(7) 0.057(8) 0.071(9) 0.013(6) -0.001(6) 0.001(5) C6 0.026(6) 0.054(7) 0.060(8) 0.004(6) 0.001(5) 0.012(5) C7 0.040(7) 0.031(6) 0.049(7) 0.004(5) 0.010(5) 0.007(5) C9 0.049(8) 0.035(6) 0.032(6) -0.012(4) -0.004(5) 0.009(5) C10 0.058(8) 0.033(6) 0.054(7) -0.002(5) 0.004(6) 0.009(5) C11 0.052(8) 0.049(7) 0.057(8) -0.007(6) -0.014(7) 0.015(6) C12 0.024(7) 0.074(9) 0.072(10) -0.009(7) -0.012(6) 0.017(6) C13 0.027(7) 0.056(8) 0.109(12) -0.029(8) 0.023(7) -0.004(6) C14 0.045(7) 0.034(6) 0.065(8) -0.007(5) 0.014(6) -0.001(5) C15 0.074(10) 0.045(7) 0.075(10) 0.005(6) 0.020(8) -0.003(7) C16 0.090(11) 0.059(8) 0.057(9) 0.016(7) 0.011(8) 0.014(8) _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 2.049(9) . ? Zn1 N8 2.087(9) . ? Zn1 Br2 2.3291(18) . ? Zn1 Br1 2.345(2) . ? N1 C6 1.326(13) . ? N1 C2 1.347(13) . ? N8 C7 1.285(15) . ? N8 C9 1.419(15) . ? C2 C3 1.399(15) . ? C2 C7 1.468(15) . ? C3 C4 1.342(18) . ? C4 C5 1.343(18) . ? C5 C6 1.399(17) . ? C9 C10 1.400(16) . ? C9 C14 1.426(17) . ? C10 C11 1.347(17) . ? C10 C16 1.547(19) . ? C11 C12 1.36(2) . ? C12 C13 1.39(2) . ? C13 C14 1.390(17) . ? C14 C15 1.498(18) . ? 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 N8 81.1(4) . . ? N1 Zn1 Br2 110.6(3) . . ? N8 Zn1 Br2 124.3(3) . . ? N1 Zn1 Br1 109.3(3) . . ? N8 Zn1 Br1 107.1(3) . . ? Br2 Zn1 Br1 118.03(7) . . ? C6 N1 C2 118.7(10) . . ? C6 N1 Zn1 128.6(8) . . ? C2 N1 Zn1 112.7(7) . . ? C7 N8 C9 121.0(9) . . ? C7 N8 Zn1 110.3(8) . . ? C9 N8 Zn1 127.9(7) . . ? N1 C2 C3 122.0(11) . . ? N1 C2 C7 114.5(9) . . ? C3 C2 C7 123.5(11) . . ? C4 C3 C2 118.5(12) . . ? C3 C4 C5 119.8(11) . . ? C4 C5 C6 120.8(11) . . ? N1 C6 C5 120.2(12) . . ? N8 C7 C2 120.9(10) . . ? C10 C9 N8 121.4(11) . . ? C10 C9 C14 120.7(11) . . ? N8 C9 C14 117.9(10) . . ? C11 C10 C9 120.1(13) . . ? C11 C10 C16 120.4(12) . . ? C9 C10 C16 119.4(11) . . ? C10 C11 C12 120.1(12) . . ? C11 C12 C13 121.9(11) . . ? C12 C13 C14 120.0(13) . . ? C13 C14 C9 117.1(12) . . ? C13 C14 C15 122.4(12) . . ? C9 C14 C15 120.4(11) . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 1.306 _refine_diff_density_min -1.401 _refine_diff_density_rms 0.263 #====End data_3.H2O _database_code_depnum_ccdc_archive 'CCDC 813733' #TrackingRef 'CCDC 753978.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H12 Cl2 N2 O2 Pd' _chemical_formula_weight 393.54 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 10.068(4) _cell_length_b 15.311(6) _cell_length_c 18.234(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2811(2) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 120 _cell_measurement_theta_min 1.5 _cell_measurement_theta_max 25.0 _exptl_crystal_description rectangle _exptl_crystal_colour redish_yellow _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.860 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1552 _exptl_absorpt_coefficient_mu 1.698 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.70 _exptl_absorpt_correction_T_max 0.82 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'BRUKER SMART APEX II CCD AREA DETECTOR' _diffrn_measurement_method Omega_scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17497 _diffrn_reflns_av_R_equivalents 0.0812 _diffrn_reflns_av_sigmaI/netI 0.0511 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2467 _reflns_number_gt 1859 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART APEX II' _computing_cell_refinement 'BRUKER SMART APEX II' _computing_data_reduction 'BRUKER AXS SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0361P)^2^+3.2791P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2467 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0540 _refine_ls_R_factor_gt 0.0344 _refine_ls_wR_factor_ref 0.0963 _refine_ls_wR_factor_gt 0.0821 _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_restrained_S_all 1.089 _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 Pd1 Pd 0.97310(4) 0.03586(2) 0.717147(18) 0.03549(15) Uani 1 1 d . . . Cl1 Cl 0.99984(16) 0.05084(9) 0.59282(7) 0.0577(4) Uani 1 1 d . . . Cl2 Cl 1.12030(13) -0.07813(9) 0.71705(7) 0.0488(3) Uani 1 1 d . . . N1 N 0.8376(4) 0.1333(2) 0.7252(2) 0.0380(9) Uani 1 1 d . . . C2 C 0.7875(5) 0.1413(3) 0.7943(3) 0.0389(11) Uani 1 1 d . . . C7 C 0.8438(5) 0.0809(3) 0.8471(3) 0.0414(11) Uani 1 1 d . . . H7 H 0.8126 0.0794 0.8951 0.050 Uiso 1 1 calc R . . C9 C 0.9944(5) -0.0307(3) 0.8774(2) 0.0375(11) Uani 1 1 d . . . C13 C 0.9776(5) -0.1541(3) 0.9575(3) 0.0465(12) Uani 1 1 d . . . H13A H 0.9266 -0.1968 0.9803 0.056 Uiso 1 1 calc R . . C12 C 1.1137(5) -0.1504(3) 0.9698(3) 0.0411(11) Uani 1 1 d . . . C10 C 1.1297(5) -0.0273(3) 0.8907(3) 0.0462(12) Uani 1 1 d . . . H10 H 1.1814 0.0150 0.8677 0.055 Uiso 1 1 calc R . . C11 C 1.1877(5) -0.0856(3) 0.9374(3) 0.0471(12) Uani 1 1 d . . . H11A H 1.2781 -0.0814 0.9473 0.057 Uiso 1 1 calc R . . C14 C 0.9187(5) -0.0941(3) 0.9116(3) 0.0428(11) Uani 1 1 d . . . H14 H 0.8276 -0.0964 0.9035 0.051 Uiso 1 1 calc R . . C3 C 0.6926(5) 0.2039(3) 0.8111(3) 0.0477(13) Uani 1 1 d . . . H3 H 0.6614 0.2097 0.8589 0.057 Uiso 1 1 calc R . . C6 C 0.7907(5) 0.1861(3) 0.6729(3) 0.0524(14) Uani 1 1 d . . . H6 H 0.8247 0.1812 0.6256 0.063 Uiso 1 1 calc R . . C5 C 0.6931(6) 0.2477(4) 0.6866(3) 0.0593(15) Uani 1 1 d . . . H5 H 0.6604 0.2824 0.6488 0.071 Uiso 1 1 calc R . . C4 C 0.6454(5) 0.2570(3) 0.7568(3) 0.0546(14) Uani 1 1 d . . . H4 H 0.5816 0.2991 0.7673 0.065 Uiso 1 1 calc R . . O1 O 1.1804(4) -0.2090(2) 1.0129(2) 0.0583(10) Uani 1 1 d . . . H1 H 1.1287 -0.2466 1.0273 0.087 Uiso 1 1 calc R . . N8 N 0.9375(4) 0.0294(2) 0.8265(2) 0.0344(8) Uani 1 1 d . . . O1W O 1.0345(4) -0.3404(3) 1.0619(2) 0.0696(12) Uani 1 1 d . . . H2W H 1.0495 -0.3703 1.1042 0.104 Uiso 1 1 d R . . H1W H 1.1067 -0.3582 1.0413 0.104 Uiso 1 1 d R . . 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 Pd1 0.0430(2) 0.0322(2) 0.0313(2) 0.00130(15) 0.00120(15) -0.00206(15) Cl1 0.0843(10) 0.0569(9) 0.0320(6) 0.0017(6) 0.0031(6) -0.0038(7) Cl2 0.0527(7) 0.0460(8) 0.0477(7) -0.0009(6) 0.0080(6) 0.0087(6) N1 0.045(2) 0.028(2) 0.040(2) 0.0019(17) -0.0059(18) -0.0031(17) C2 0.042(3) 0.033(3) 0.041(3) -0.001(2) -0.006(2) -0.002(2) C7 0.051(3) 0.042(3) 0.031(2) 0.001(2) 0.000(2) 0.000(2) C9 0.051(3) 0.033(3) 0.029(2) -0.0020(19) 0.001(2) 0.005(2) C13 0.047(3) 0.049(3) 0.043(3) 0.010(2) -0.001(2) -0.005(2) C12 0.051(3) 0.036(3) 0.036(2) 0.001(2) -0.008(2) 0.002(2) C10 0.042(3) 0.047(3) 0.050(3) 0.009(2) -0.003(2) -0.009(2) C11 0.042(3) 0.049(3) 0.050(3) 0.004(3) -0.005(2) -0.004(2) C14 0.039(3) 0.047(3) 0.043(3) 0.009(2) -0.003(2) -0.003(2) C3 0.052(3) 0.034(3) 0.057(3) -0.003(2) 0.002(3) 0.003(2) C6 0.064(4) 0.046(3) 0.047(3) 0.013(3) -0.009(3) -0.005(3) C5 0.068(4) 0.039(3) 0.070(4) 0.015(3) -0.014(3) 0.008(3) C4 0.048(3) 0.038(3) 0.078(4) 0.004(3) -0.008(3) 0.007(2) O1 0.062(2) 0.052(2) 0.061(2) 0.0173(19) -0.018(2) -0.0011(19) N8 0.038(2) 0.032(2) 0.0328(19) -0.0001(16) 0.0038(16) 0.0029(16) O1W 0.087(3) 0.060(3) 0.062(3) 0.016(2) 0.002(2) -0.004(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 Pd1 N1 2.026(4) . ? Pd1 N8 2.028(4) . ? Pd1 Cl2 2.2898(15) . ? Pd1 Cl1 2.2943(16) . ? N1 C6 1.337(6) . ? N1 C2 1.364(6) . ? C2 C3 1.387(7) . ? C2 C7 1.450(6) . ? C7 N8 1.286(6) . ? C9 C14 1.382(7) . ? C9 C10 1.385(6) . ? C9 N8 1.427(6) . ? C13 C14 1.377(7) . ? C13 C12 1.389(7) . ? C12 O1 1.369(6) . ? C12 C11 1.375(7) . ? C10 C11 1.364(7) . ? C3 C4 1.366(7) . ? C6 C5 1.386(8) . ? C5 C4 1.375(8) . ? 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 Pd1 N8 81.14(15) . . ? N1 Pd1 Cl2 175.38(11) . . ? N8 Pd1 Cl2 94.46(11) . . ? N1 Pd1 Cl1 94.42(11) . . ? N8 Pd1 Cl1 175.51(11) . . ? Cl2 Pd1 Cl1 89.97(5) . . ? C6 N1 C2 118.3(4) . . ? C6 N1 Pd1 129.1(4) . . ? C2 N1 Pd1 112.5(3) . . ? N1 C2 C3 121.4(4) . . ? N1 C2 C7 114.2(4) . . ? C3 C2 C7 124.3(5) . . ? N8 C7 C2 119.0(4) . . ? C14 C9 C10 119.3(4) . . ? C14 C9 N8 121.7(4) . . ? C10 C9 N8 118.9(4) . . ? C14 C13 C12 119.7(5) . . ? O1 C12 C11 117.0(4) . . ? O1 C12 C13 123.3(5) . . ? C11 C12 C13 119.6(4) . . ? C11 C10 C9 120.3(5) . . ? C10 C11 C12 120.6(5) . . ? C13 C14 C9 120.3(5) . . ? C4 C3 C2 119.4(5) . . ? N1 C6 C5 122.3(5) . . ? C4 C5 C6 119.1(5) . . ? C3 C4 C5 119.5(5) . . ? C7 N8 C9 120.0(4) . . ? C7 N8 Pd1 112.8(3) . . ? C9 N8 Pd1 126.9(3) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.835 _refine_diff_density_min -0.373 _refine_diff_density_rms 0.131