# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Raju Mondal' _publ_contact_author_email icrm@iacs.res.in _publ_author_name 'Raju Mondal' data_new1 _database_code_depnum_ccdc_archive 'CCDC 774721' #TrackingRef '- Compound 1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H26 Cl6 N4 O6 Zn' _chemical_formula_weight 912.70 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 Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 24.303(10) _cell_length_b 10.137(4) _cell_length_c 18.744(13) _cell_angle_alpha 90.00 _cell_angle_beta 125.506(4) _cell_angle_gamma 90.00 _cell_volume 3759(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2103 _cell_measurement_theta_min 2.26 _cell_measurement_theta_max 25.2 _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.613 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1848 _exptl_absorpt_coefficient_mu 1.134 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.801100 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ; SADABS v.2.03 (Bruker, 2001), R(int)=0.0919 before correction ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 APEX-2 CCD area detector' _diffrn_measurement_method '/w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_decay_% 0 _diffrn_reflns_number 11707 _diffrn_reflns_av_R_equivalents 0.0567 _diffrn_reflns_av_sigmaI/netI 0.0600 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 24.63 _reflns_number_total 3143 _reflns_number_gt 1762 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX-2' _computing_cell_refinement 'Bruker APEX-2' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0515P)^2^+8.0711P] 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 3143 _refine_ls_number_parameters 249 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1148 _refine_ls_R_factor_gt 0.0504 _refine_ls_wR_factor_ref 0.1415 _refine_ls_wR_factor_gt 0.1091 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 0.0000 0.93448(8) 0.2500 0.0525(3) Uani 1 2 d S . . Cl1 Cl 0.19384(8) 0.78795(17) 0.28088(11) 0.0878(5) Uani 1 1 d . . . Cl2 Cl 0.30712(9) 0.5774(2) 0.35536(15) 0.1154(7) Uani 1 1 d . . . Cl3 Cl 0.25140(9) 0.40617(17) 0.57519(12) 0.1060(6) Uani 1 1 d . . . N1 N 0.01013(19) 1.0627(4) 0.3400(3) 0.0523(10) Uani 1 1 d . . . C1 C 0.1667(2) 0.6886(5) 0.3929(3) 0.0534(13) Uani 1 1 d . . . O1 O 0.08497(19) 0.8453(4) 0.2905(3) 0.0788(12) Uani 1 1 d . . . C2 C 0.2068(2) 0.6834(5) 0.3611(3) 0.0572(14) Uani 1 1 d . . . O2 O 0.0738(2) 0.7711(4) 0.3902(3) 0.1004(15) Uani 1 1 d . . . N2 N 0.1243(3) 1.6609(5) 0.7867(3) 0.0781(15) Uani 1 1 d . . . H2A H 0.1334 1.7142 0.8279 0.094 Uiso 1 1 calc R . . C3 C 0.2587(3) 0.5921(6) 0.3956(4) 0.0688(16) Uani 1 1 d . . . O3 O 0.14389(18) 0.6052(4) 0.4934(2) 0.0766(12) Uani 1 1 d . . . H3A H 0.1135 0.6598 0.4664 0.115 Uiso 1 1 calc R . . C4 C 0.2719(3) 0.5083(6) 0.4603(4) 0.0728(17) Uani 1 1 d . . . H4A H 0.3066 0.4470 0.4823 0.087 Uiso 1 1 calc R . . C5 C 0.2342(3) 0.5134(5) 0.4937(3) 0.0625(15) Uani 1 1 d . . . C6 C 0.1815(2) 0.6024(5) 0.4606(3) 0.0577(14) Uani 1 1 d . . . C7 C 0.1041(3) 0.7761(6) 0.3537(4) 0.0677(16) Uani 1 1 d . . . C8 C -0.0271(3) 1.0553(6) 0.3710(4) 0.0689(15) Uani 1 1 d . . . H8A H -0.0609 0.9916 0.3476 0.083 Uiso 1 1 calc R . . C9 C -0.0187(3) 1.1358(6) 0.4350(4) 0.0772(17) Uani 1 1 d . . . H9A H -0.0460 1.1256 0.4544 0.093 Uiso 1 1 calc R . . C10 C 0.0300(3) 1.2314(6) 0.4706(4) 0.0642(15) Uani 1 1 d . . . C11 C 0.0683(3) 1.2420(5) 0.4385(4) 0.0658(15) Uani 1 1 d . . . H11A H 0.1018 1.3061 0.4605 0.079 Uiso 1 1 calc R . . C12 C 0.0571(2) 1.1572(5) 0.3735(4) 0.0604(14) Uani 1 1 d . . . H12A H 0.0832 1.1664 0.3523 0.073 Uiso 1 1 calc R . . C13 C 0.0400(3) 1.3159(6) 0.5422(4) 0.0794(18) Uani 1 1 d . . . H13A H 0.0124 1.2999 0.5606 0.095 Uiso 1 1 calc R . . C14 C 0.0831(3) 1.4077(6) 0.5802(4) 0.0780(18) Uani 1 1 d . . . H14A H 0.1105 1.4224 0.5614 0.094 Uiso 1 1 calc R . . C15 C 0.0947(3) 1.4946(5) 0.6520(3) 0.0598(14) Uani 1 1 d . . . C16 C 0.0618(3) 1.4841(6) 0.6921(4) 0.0661(15) Uani 1 1 d . . . H16A H 0.0286 1.4204 0.6737 0.079 Uiso 1 1 calc R . . C17 C 0.0785(3) 1.5684(6) 0.7590(4) 0.0707(16) Uani 1 1 d . . . H17A H 0.0565 1.5596 0.7860 0.085 Uiso 1 1 calc R . . C18 C 0.1556(3) 1.6688(6) 0.7490(4) 0.0844(19) Uani 1 1 d . . . H18A H 0.1889 1.7329 0.7690 0.101 Uiso 1 1 calc R . . C19 C 0.1427(3) 1.5894(6) 0.6827(4) 0.0777(17) Uani 1 1 d . . . H19A H 0.1666 1.6001 0.6584 0.093 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 0.0468(5) 0.0504(5) 0.0540(5) 0.000 0.0257(4) 0.000 Cl1 0.0832(11) 0.0970(13) 0.0942(12) 0.0147(10) 0.0579(10) -0.0083(9) Cl2 0.0977(12) 0.1287(17) 0.1618(19) -0.0030(14) 0.0992(14) 0.0040(12) Cl3 0.1052(13) 0.0964(14) 0.0827(12) 0.0373(10) 0.0353(10) 0.0128(10) N1 0.050(2) 0.050(3) 0.052(2) 0.004(2) 0.026(2) 0.000(2) C1 0.035(2) 0.049(3) 0.063(3) -0.004(3) 0.021(2) -0.004(2) O1 0.074(3) 0.073(3) 0.067(3) 0.017(2) 0.028(2) 0.022(2) C2 0.047(3) 0.048(3) 0.056(3) 0.000(3) 0.018(3) -0.011(2) O2 0.083(3) 0.105(4) 0.141(4) 0.034(3) 0.081(3) 0.026(3) N2 0.089(4) 0.080(4) 0.067(3) -0.022(3) 0.046(3) 0.002(3) C3 0.053(3) 0.075(4) 0.083(4) -0.007(4) 0.042(3) -0.003(3) O3 0.078(3) 0.097(3) 0.078(3) 0.004(2) 0.059(2) -0.008(2) C4 0.054(3) 0.061(4) 0.084(4) 0.006(3) 0.028(3) 0.012(3) C5 0.056(3) 0.055(3) 0.055(3) 0.008(3) 0.020(3) 0.003(3) C6 0.049(3) 0.047(3) 0.060(3) 0.004(3) 0.021(3) -0.001(2) C7 0.052(3) 0.058(4) 0.083(4) -0.004(3) 0.034(3) -0.007(3) C8 0.071(3) 0.073(4) 0.067(4) -0.016(3) 0.042(3) -0.020(3) C9 0.077(4) 0.089(5) 0.074(4) -0.018(4) 0.048(4) -0.017(4) C10 0.071(4) 0.066(4) 0.050(3) -0.002(3) 0.032(3) 0.007(3) C11 0.061(3) 0.052(3) 0.055(4) -0.005(3) 0.017(3) -0.012(3) C12 0.056(3) 0.053(3) 0.065(4) 0.002(3) 0.031(3) -0.006(3) C13 0.072(4) 0.084(5) 0.080(5) 0.004(4) 0.043(4) 0.005(4) C14 0.074(4) 0.073(4) 0.080(4) 0.005(4) 0.041(4) -0.004(3) C15 0.070(3) 0.054(3) 0.046(3) -0.007(3) 0.028(3) 0.005(3) C16 0.065(3) 0.063(4) 0.057(4) -0.006(3) 0.028(3) -0.004(3) C17 0.064(3) 0.085(5) 0.068(4) -0.008(4) 0.041(3) 0.000(3) C18 0.098(5) 0.086(5) 0.084(5) -0.025(4) 0.061(4) -0.022(4) C19 0.091(4) 0.081(5) 0.073(4) -0.015(4) 0.054(4) -0.011(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 O1 1.959(4) 2 ? Zn1 O1 1.959(4) . ? Zn1 N1 2.028(4) . ? Zn1 N1 2.028(4) 2 ? Cl1 C2 1.713(5) . ? Cl2 C3 1.734(6) . ? Cl3 C5 1.717(6) . ? N1 C8 1.332(6) . ? N1 C12 1.335(6) . ? C1 C6 1.405(7) . ? C1 C2 1.407(7) . ? C1 C7 1.530(7) . ? O1 C7 1.213(7) . ? C2 C3 1.386(7) . ? O2 C7 1.264(7) . ? N2 C18 1.305(7) . ? N2 C17 1.310(7) . ? N2 H2A 0.8600 . ? C3 C4 1.358(8) . ? O3 C6 1.366(6) . ? O3 H3A 0.8200 . ? C4 C5 1.377(8) . ? C4 H4A 0.9300 . ? C5 C6 1.385(7) . ? C8 C9 1.365(7) . ? C8 H8A 0.9300 . ? C9 C10 1.366(7) . ? C9 H9A 0.9300 . ? C10 C11 1.377(8) . ? C10 C13 1.488(8) . ? C11 C12 1.382(7) . ? C11 H11A 0.9300 . ? C12 H12A 0.9300 . ? C13 C14 1.266(7) . ? C13 H13A 0.9300 . ? C14 C15 1.491(8) . ? C14 H14A 0.9300 . ? C15 C19 1.355(7) . ? C15 C16 1.384(7) . ? C16 C17 1.370(7) . ? C16 H16A 0.9300 . ? C17 H17A 0.9300 . ? C18 C19 1.356(8) . ? C18 H18A 0.9300 . ? C19 H19A 0.9300 . ? 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 O1 Zn1 O1 125.0(2) 2 . ? O1 Zn1 N1 102.12(17) 2 . ? O1 Zn1 N1 112.44(16) . . ? O1 Zn1 N1 112.44(16) 2 2 ? O1 Zn1 N1 102.12(17) . 2 ? N1 Zn1 N1 100.3(2) . 2 ? C8 N1 C12 116.5(5) . . ? C8 N1 Zn1 122.8(4) . . ? C12 N1 Zn1 120.6(4) . . ? C6 C1 C2 118.9(4) . . ? C6 C1 C7 117.1(5) . . ? C2 C1 C7 123.9(5) . . ? C7 O1 Zn1 111.5(4) . . ? C3 C2 C1 119.6(5) . . ? C3 C2 Cl1 118.4(4) . . ? C1 C2 Cl1 122.0(4) . . ? C18 N2 C17 117.2(5) . . ? C18 N2 H2A 121.4 . . ? C17 N2 H2A 121.4 . . ? C4 C3 C2 120.9(5) . . ? C4 C3 Cl2 117.8(5) . . ? C2 C3 Cl2 121.2(5) . . ? C6 O3 H3A 109.5 . . ? C3 C4 C5 120.5(5) . . ? C3 C4 H4A 119.7 . . ? C5 C4 H4A 119.7 . . ? C4 C5 C6 120.5(5) . . ? C4 C5 Cl3 119.9(4) . . ? C6 C5 Cl3 119.6(5) . . ? O3 C6 C5 120.0(5) . . ? O3 C6 C1 120.4(4) . . ? C5 C6 C1 119.6(5) . . ? O1 C7 O2 122.5(6) . . ? O1 C7 C1 121.0(6) . . ? O2 C7 C1 116.6(6) . . ? N1 C8 C9 123.9(5) . . ? N1 C8 H8A 118.1 . . ? C9 C8 H8A 118.1 . . ? C8 C9 C10 119.9(6) . . ? C8 C9 H9A 120.0 . . ? C10 C9 H9A 120.0 . . ? C9 C10 C11 117.1(5) . . ? C9 C10 C13 119.4(6) . . ? C11 C10 C13 123.5(6) . . ? C10 C11 C12 120.0(5) . . ? C10 C11 H11A 120.0 . . ? C12 C11 H11A 120.0 . . ? N1 C12 C11 122.6(5) . . ? N1 C12 H12A 118.7 . . ? C11 C12 H12A 118.7 . . ? C14 C13 C10 125.4(6) . . ? C14 C13 H13A 117.3 . . ? C10 C13 H13A 117.3 . . ? C13 C14 C15 127.1(6) . . ? C13 C14 H14A 116.4 . . ? C15 C14 H14A 116.4 . . ? C19 C15 C16 116.7(5) . . ? C19 C15 C14 117.9(6) . . ? C16 C15 C14 125.3(6) . . ? C17 C16 C15 119.4(5) . . ? C17 C16 H16A 120.3 . . ? C15 C16 H16A 120.3 . . ? N2 C17 C16 122.8(5) . . ? N2 C17 H17A 118.6 . . ? C16 C17 H17A 118.6 . . ? N2 C18 C19 124.2(6) . . ? N2 C18 H18A 117.9 . . ? C19 C18 H18A 117.9 . . ? C15 C19 C18 119.6(6) . . ? C15 C19 H19A 120.2 . . ? C18 C19 H19A 120.2 . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 24.63 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.452 _refine_diff_density_min -0.376 _refine_diff_density_rms 0.067 # Attachment '- Compound 2.cif' data_09tba040 _database_code_depnum_ccdc_archive 'CCDC 774722' #TrackingRef '- Compound 2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C68 H36 Cl12 N8 O12 Zn4' _chemical_formula_weight 1843.93 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.9481(8) _cell_length_b 13.2205(9) _cell_length_c 13.9222(16) _cell_angle_alpha 106.761(3) _cell_angle_beta 102.853(3) _cell_angle_gamma 108.249(2) _cell_volume 1720.6(3) _cell_formula_units_Z 1 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 7100 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 26.16 _exptl_crystal_description Block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.780 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 920 _exptl_absorpt_coefficient_mu 1.914 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.802189 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS v.2.03 (Bruker, 2001), R(int)=0.0548 before correction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 APEX-2 CCD area detector' _diffrn_measurement_method '/w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_decay_% 0 _diffrn_reflns_number 23078 _diffrn_reflns_av_R_equivalents 0.0283 _diffrn_reflns_av_sigmaI/netI 0.0332 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 27.50 _reflns_number_total 7561 _reflns_number_gt 5957 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX-2' _computing_cell_refinement 'Bruker APEX-2' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0351P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7561 _refine_ls_number_parameters 469 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0436 _refine_ls_R_factor_gt 0.0299 _refine_ls_wR_factor_ref 0.0719 _refine_ls_wR_factor_gt 0.0681 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _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 0.26171(2) 0.54756(2) 0.422615(19) 0.02959(7) Uani 1 1 d . . . Zn2 Zn 0.31502(2) 0.17262(2) 0.243668(18) 0.03146(7) Uani 1 1 d . . . Cl1 Cl 0.17239(8) 0.48440(7) 0.09268(6) 0.0664(2) Uani 1 1 d . . . Cl2 Cl 0.25170(8) 0.45230(7) -0.11209(5) 0.0680(2) Uani 1 1 d . . . Cl3 Cl 0.54667(7) 0.22528(6) 0.00071(6) 0.05928(18) Uani 1 1 d . . . Cl4 Cl 0.10124(6) 0.74468(7) 0.24374(6) 0.0661(2) Uani 1 1 d . . . Cl5 Cl 0.61486(7) 1.02056(6) 0.31372(6) 0.05561(18) Uani 1 1 d . . . Cl6 Cl 0.72631(6) 0.94286(6) 0.49368(5) 0.04948(16) Uani 1 1 d . . . O1 O 0.32028(15) 0.49243(13) 0.30025(12) 0.0371(4) Uani 1 1 d . . . N1 N 0.23543(18) 0.01765(16) 0.09931(14) 0.0371(4) Uani 1 1 d . . . C1 C 0.0389(3) -0.1493(2) -0.0243(2) 0.0536(7) Uani 1 1 d . . . H1A H -0.0512 -0.1997 -0.0415 0.064 Uiso 1 1 calc R . . O2 O 0.25621(16) 0.30755(13) 0.27512(12) 0.0399(4) Uani 1 1 d . . . N2 N 0.11683(17) 0.06998(15) 0.23927(14) 0.0353(4) Uani 1 1 d . . . C2 C -0.1373(3) -0.0682(2) 0.2277(2) 0.0563(7) Uani 1 1 d . . . H2A H -0.2237 -0.1149 0.2232 0.068 Uiso 1 1 calc R . . O3 O 0.59492(15) 0.84757(12) 0.62918(11) 0.0373(4) Uani 1 1 d . . . N3 N 0.24371(17) 0.44621(15) 0.51298(13) 0.0314(4) Uani 1 1 d . . . C3 C 0.3353(3) 0.3778(2) 0.6396(2) 0.0496(6) Uani 1 1 d . . . H3A H 0.4113 0.3772 0.6850 0.059 Uiso 1 1 calc R . . O4 O 0.45182(15) 0.66607(12) 0.53196(12) 0.0376(4) Uani 1 1 d . . . N4 N 0.04531(17) 0.44726(15) 0.36648(14) 0.0323(4) Uani 1 1 d . . . O5 O 0.44690(14) 0.25381(13) 0.18441(11) 0.0360(3) Uani 1 1 d . . . C5 C 0.3004(3) -0.0015(2) 0.0295(2) 0.0485(6) Uani 1 1 d . . . H5A H 0.3906 0.0492 0.0478 0.058 Uiso 1 1 calc R . . O6 O 0.22464(14) 0.68020(12) 0.41006(12) 0.0346(3) Uani 1 1 d . . . C6 C 0.1064(3) -0.1666(2) -0.0952(2) 0.0614(8) Uani 1 1 d . . . H6A H 0.0622 -0.2279 -0.1614 0.074 Uiso 1 1 calc R . . C7 C -0.0594(3) 0.0324(2) 0.3146(2) 0.0522(7) Uani 1 1 d . . . H7A H -0.0910 0.0552 0.3705 0.063 Uiso 1 1 calc R . . C8 C -0.0870(2) -0.1005(2) 0.1462(2) 0.0500(6) Uani 1 1 d . . . H8A H -0.1389 -0.1691 0.0868 0.060 Uiso 1 1 calc R . . C9 C 0.2045(3) 0.3091(2) 0.62820(19) 0.0487(6) Uani 1 1 d . . . H9A H 0.1916 0.2633 0.6678 0.058 Uiso 1 1 calc R . . C10 C 0.4000(2) 0.3463(2) -0.03774(18) 0.0441(6) Uani 1 1 d . . . H10A H 0.4275 0.3411 -0.0969 0.053 Uiso 1 1 calc R . . C11 C 0.2755(2) 0.7992(2) 0.31519(18) 0.0379(5) Uani 1 1 d . . . C12 C -0.1876(2) 0.3897(2) 0.26282(19) 0.0430(6) Uani 1 1 d . . . H12A H -0.2509 0.3948 0.2096 0.052 Uiso 1 1 calc R . . C13 C 0.3649(2) 0.8785(2) 0.29184(19) 0.0423(6) Uani 1 1 d . . . H13A H 0.3332 0.9033 0.2390 0.051 Uiso 1 1 calc R . . C14 C -0.0486(2) 0.45402(19) 0.29212(18) 0.0388(5) Uani 1 1 d . . . H14A H -0.0198 0.5039 0.2586 0.047 Uiso 1 1 calc R . . C15 C 0.0677(2) 0.0994(2) 0.31723(19) 0.0447(6) Uani 1 1 d . . . H15A H 0.1212 0.1681 0.3762 0.054 Uiso 1 1 calc R . . C16 C 0.2398(3) -0.0927(2) -0.0677(2) 0.0572(7) Uani 1 1 d . . . H16A H 0.2883 -0.1040 -0.1140 0.069 Uiso 1 1 calc R . . C17 C 0.3156(2) 0.4027(2) -0.01859(18) 0.0439(6) Uani 1 1 d . . . C18 C 0.4432(2) 0.2979(2) 0.03059(18) 0.0389(5) Uani 1 1 d . . . C19 C -0.2298(2) 0.3180(2) 0.31420(19) 0.0431(6) Uani 1 1 d . . . H19A H -0.3226 0.2745 0.2967 0.052 Uiso 1 1 calc R . . C20 C 0.1055(2) -0.05626(19) 0.07333(17) 0.0347(5) Uani 1 1 d . . . C21 C 0.2817(2) 0.4164(2) 0.07294(18) 0.0392(5) Uani 1 1 d . . . C22 C 0.0928(2) 0.3083(2) 0.55832(18) 0.0410(5) Uani 1 1 d . . . H22A H 0.0041 0.2633 0.5509 0.049 Uiso 1 1 calc R . . C23 C -0.1337(2) 0.3112(2) 0.39183(18) 0.0380(5) Uani 1 1 d . . . H23A H -0.1608 0.2628 0.4271 0.046 Uiso 1 1 calc R . . C24 C 0.3279(2) 0.36944(18) 0.14429(16) 0.0319(5) Uani 1 1 d . . . C25 C 0.5504(2) 0.88711(18) 0.42828(17) 0.0320(5) Uani 1 1 d . . . C26 C 0.1160(2) 0.37649(18) 0.49923(16) 0.0302(5) Uani 1 1 d . . . C27 C 0.3505(2) 0.4469(2) 0.58226(18) 0.0408(5) Uani 1 1 d . . . H27A H 0.4384 0.4960 0.5920 0.049 Uiso 1 1 calc R . . C28 C 0.3168(2) 0.75757(17) 0.39404(16) 0.0291(4) Uani 1 1 d . . . C30 C 0.5039(2) 0.92169(19) 0.34816(19) 0.0368(5) Uani 1 1 d . . . C31 C 0.4074(2) 0.30381(18) 0.12338(16) 0.0318(5) Uani 1 1 d . . . C32 C 0.0043(2) 0.37727(18) 0.41700(16) 0.0303(5) Uani 1 1 d . . . C34 C 0.0411(2) -0.02969(19) 0.15453(18) 0.0354(5) Uani 1 1 d . . . C36 C 0.5046(2) 0.76969(18) 0.54346(16) 0.0288(4) Uani 1 1 d . . . C38 C 0.2989(2) 0.39072(19) 0.24731(16) 0.0305(5) Uani 1 1 d . . . C39 C 0.4587(2) 0.80592(17) 0.45348(16) 0.0280(4) 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 0.02817(13) 0.02713(14) 0.03080(14) 0.01209(11) 0.00940(10) 0.00755(11) Zn2 0.02926(13) 0.03047(15) 0.02805(14) 0.00876(11) 0.00651(10) 0.00849(11) Cl1 0.0796(5) 0.0803(5) 0.0635(4) 0.0396(4) 0.0233(4) 0.0528(5) Cl2 0.0725(5) 0.0713(5) 0.0463(4) 0.0376(4) 0.0033(3) 0.0100(4) Cl3 0.0566(4) 0.0633(5) 0.0597(4) 0.0149(4) 0.0361(3) 0.0234(4) Cl4 0.0339(3) 0.0806(5) 0.0852(5) 0.0573(4) 0.0023(3) 0.0146(3) Cl5 0.0508(4) 0.0589(4) 0.0801(5) 0.0481(4) 0.0378(3) 0.0208(3) Cl6 0.0283(3) 0.0536(4) 0.0603(4) 0.0274(3) 0.0120(3) 0.0060(3) O1 0.0423(9) 0.0296(9) 0.0343(8) 0.0070(7) 0.0162(7) 0.0110(7) N1 0.0357(10) 0.0355(11) 0.0340(10) 0.0080(9) 0.0102(8) 0.0131(9) C1 0.0453(15) 0.0373(15) 0.0540(17) -0.0003(13) 0.0066(13) 0.0102(12) O2 0.0496(10) 0.0360(9) 0.0427(9) 0.0193(8) 0.0243(8) 0.0187(8) N2 0.0302(10) 0.0327(11) 0.0346(10) 0.0079(9) 0.0080(8) 0.0090(8) C2 0.0365(14) 0.0472(17) 0.077(2) 0.0203(16) 0.0236(14) 0.0078(13) O3 0.0355(8) 0.0305(8) 0.0309(8) 0.0083(7) -0.0003(7) 0.0060(7) N3 0.0300(9) 0.0314(10) 0.0315(10) 0.0119(8) 0.0111(8) 0.0107(8) C3 0.0523(16) 0.0580(17) 0.0451(15) 0.0265(13) 0.0130(12) 0.0273(14) O4 0.0368(8) 0.0285(9) 0.0360(9) 0.0138(7) 0.0019(7) 0.0050(7) N4 0.0283(9) 0.0280(10) 0.0343(10) 0.0101(8) 0.0085(8) 0.0070(8) O5 0.0313(8) 0.0414(9) 0.0366(8) 0.0156(7) 0.0126(7) 0.0151(7) C5 0.0485(15) 0.0438(15) 0.0469(15) 0.0100(13) 0.0178(12) 0.0167(13) O6 0.0270(7) 0.0342(9) 0.0468(9) 0.0220(7) 0.0141(7) 0.0107(7) C6 0.069(2) 0.0502(18) 0.0435(16) -0.0067(13) 0.0121(14) 0.0255(16) C7 0.0429(14) 0.0566(18) 0.0594(17) 0.0207(15) 0.0258(13) 0.0187(13) C8 0.0354(13) 0.0349(14) 0.0610(17) 0.0083(13) 0.0098(12) 0.0050(11) C9 0.0666(18) 0.0492(16) 0.0380(14) 0.0246(13) 0.0208(13) 0.0238(14) C10 0.0407(13) 0.0439(15) 0.0266(12) 0.0085(11) 0.0109(10) -0.0040(11) C11 0.0282(11) 0.0373(13) 0.0454(13) 0.0193(11) 0.0063(10) 0.0111(10) C12 0.0329(12) 0.0385(14) 0.0468(14) 0.0114(12) 0.0021(11) 0.0137(11) C13 0.0438(14) 0.0463(15) 0.0499(14) 0.0328(13) 0.0182(11) 0.0203(12) C14 0.0375(13) 0.0335(13) 0.0417(13) 0.0174(11) 0.0073(10) 0.0114(10) C15 0.0372(13) 0.0445(15) 0.0411(14) 0.0071(12) 0.0137(11) 0.0109(12) C16 0.0671(19) 0.0533(18) 0.0480(16) 0.0067(14) 0.0241(14) 0.0291(16) C17 0.0456(14) 0.0389(14) 0.0314(12) 0.0165(11) 0.0046(11) 0.0007(11) C18 0.0328(12) 0.0366(13) 0.0339(12) 0.0058(11) 0.0125(10) 0.0040(10) C19 0.0279(12) 0.0387(14) 0.0503(15) 0.0083(12) 0.0109(11) 0.0080(10) C20 0.0330(12) 0.0271(12) 0.0359(12) 0.0077(10) 0.0038(10) 0.0117(10) C21 0.0366(12) 0.0361(13) 0.0346(12) 0.0127(11) 0.0054(10) 0.0078(10) C22 0.0453(14) 0.0378(14) 0.0374(13) 0.0164(11) 0.0171(11) 0.0101(11) C23 0.0356(12) 0.0373(13) 0.0394(13) 0.0134(11) 0.0184(10) 0.0099(11) C24 0.0319(11) 0.0276(12) 0.0265(11) 0.0073(9) 0.0063(9) 0.0054(9) C25 0.0267(11) 0.0304(12) 0.0377(12) 0.0122(10) 0.0122(9) 0.0101(9) C26 0.0360(12) 0.0254(11) 0.0276(11) 0.0077(9) 0.0141(9) 0.0105(9) C27 0.0360(12) 0.0480(15) 0.0409(13) 0.0216(12) 0.0116(10) 0.0172(11) C28 0.0300(11) 0.0256(11) 0.0335(11) 0.0122(9) 0.0126(9) 0.0114(9) C30 0.0370(12) 0.0332(13) 0.0470(13) 0.0217(11) 0.0211(11) 0.0122(10) C31 0.0254(10) 0.0310(12) 0.0276(11) 0.0065(10) 0.0070(9) 0.0030(9) C32 0.0316(11) 0.0259(11) 0.0303(11) 0.0074(9) 0.0134(9) 0.0092(9) C34 0.0311(11) 0.0271(12) 0.0401(13) 0.0101(10) 0.0034(10) 0.0106(10) C36 0.0251(10) 0.0311(12) 0.0294(11) 0.0109(10) 0.0101(9) 0.0107(9) C38 0.0236(10) 0.0353(13) 0.0267(11) 0.0092(10) 0.0046(8) 0.0098(9) C39 0.0274(10) 0.0256(11) 0.0278(11) 0.0096(9) 0.0088(8) 0.0078(9) _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 O6 1.9651(14) . ? Zn1 O1 1.9766(15) . ? Zn1 O4 2.0680(15) . ? Zn1 N3 2.0818(17) . ? Zn1 N4 2.1431(17) . ? Zn2 O3 1.9591(14) 2_666 ? Zn2 O5 1.9969(15) . ? Zn2 O2 2.0452(15) . ? Zn2 N2 2.1452(18) . ? Zn2 N1 2.1735(18) . ? Cl1 C21 1.730(2) . ? Cl2 C17 1.729(2) . ? Cl3 C18 1.743(2) . ? Cl4 C11 1.740(2) . ? Cl5 C30 1.744(2) . ? Cl6 C25 1.739(2) . ? O1 C38 1.249(2) . ? N1 C5 1.339(3) . ? N1 C20 1.344(3) . ? C1 C6 1.369(4) . ? C1 C20 1.388(3) . ? C1 H1A 0.9300 . ? O2 C38 1.258(2) . ? N2 C15 1.329(3) . ? N2 C34 1.342(3) . ? C2 C7 1.365(4) . ? C2 C8 1.385(4) . ? C2 H2A 0.9300 . ? O3 C36 1.261(2) . ? O3 Zn2 1.9591(14) 2_666 ? N3 C27 1.336(3) . ? N3 C26 1.347(3) . ? C3 C27 1.373(3) . ? C3 C9 1.379(4) . ? C3 H3A 0.9300 . ? O4 C36 1.254(2) . ? N4 C14 1.332(3) . ? N4 C32 1.345(3) . ? O5 C31 1.298(2) . ? C5 C16 1.373(4) . ? C5 H5A 0.9300 . ? O6 C28 1.304(2) . ? C6 C16 1.370(4) . ? C6 H6A 0.9300 . ? C7 C15 1.382(3) . ? C7 H7A 0.9300 . ? C8 C34 1.379(3) . ? C8 H8A 0.9300 . ? C9 C22 1.378(3) . ? C9 H9A 0.9300 . ? C10 C18 1.371(3) . ? C10 C17 1.381(3) . ? C10 H10A 0.9300 . ? C11 C13 1.364(3) . ? C11 C28 1.413(3) . ? C12 C19 1.373(3) . ? C12 C14 1.385(3) . ? C12 H12A 0.9300 . ? C13 C30 1.387(3) . ? C13 H13A 0.9300 . ? C14 H14A 0.9300 . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? C17 C21 1.384(3) . ? C18 C31 1.420(3) . ? C19 C23 1.376(3) . ? C19 H19A 0.9300 . ? C20 C34 1.476(3) . ? C21 C24 1.399(3) . ? C22 C26 1.390(3) . ? C22 H22A 0.9300 . ? C23 C32 1.389(3) . ? C23 H23A 0.9300 . ? C24 C31 1.426(3) . ? C24 C38 1.504(3) . ? C25 C30 1.378(3) . ? C25 C39 1.408(3) . ? C26 C32 1.483(3) . ? C27 H27A 0.9300 . ? C28 C39 1.416(3) . ? C36 C39 1.506(3) . ? 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 O6 Zn1 O1 104.76(6) . . ? O6 Zn1 O4 86.89(6) . . ? O1 Zn1 O4 98.14(6) . . ? O6 Zn1 N3 140.34(7) . . ? O1 Zn1 N3 114.66(7) . . ? O4 Zn1 N3 91.60(6) . . ? O6 Zn1 N4 89.03(6) . . ? O1 Zn1 N4 105.02(7) . . ? O4 Zn1 N4 156.76(7) . . ? N3 Zn1 N4 77.15(6) . . ? O3 Zn2 O5 113.08(6) 2_666 . ? O3 Zn2 O2 114.48(6) 2_666 . ? O5 Zn2 O2 89.10(6) . . ? O3 Zn2 N2 91.25(6) 2_666 . ? O5 Zn2 N2 154.87(6) . . ? O2 Zn2 N2 86.17(6) . . ? O3 Zn2 N1 112.58(6) 2_666 . ? O5 Zn2 N1 89.47(7) . . ? O2 Zn2 N1 129.22(7) . . ? N2 Zn2 N1 74.74(7) . . ? C38 O1 Zn1 127.51(14) . . ? C5 N1 C20 118.5(2) . . ? C5 N1 Zn2 124.49(16) . . ? C20 N1 Zn2 116.49(15) . . ? C6 C1 C20 119.7(2) . . ? C6 C1 H1A 120.2 . . ? C20 C1 H1A 120.2 . . ? C38 O2 Zn2 123.25(14) . . ? C15 N2 C34 119.0(2) . . ? C15 N2 Zn2 123.10(15) . . ? C34 N2 Zn2 117.88(15) . . ? C7 C2 C8 119.7(2) . . ? C7 C2 H2A 120.2 . . ? C8 C2 H2A 120.2 . . ? C36 O3 Zn2 127.17(13) . 2_666 ? C27 N3 C26 119.30(18) . . ? C27 N3 Zn1 123.77(15) . . ? C26 N3 Zn1 116.93(13) . . ? C27 C3 C9 118.4(2) . . ? C27 C3 H3A 120.8 . . ? C9 C3 H3A 120.8 . . ? C36 O4 Zn1 124.59(13) . . ? C14 N4 C32 119.11(18) . . ? C14 N4 Zn1 125.70(15) . . ? C32 N4 Zn1 115.08(13) . . ? C31 O5 Zn2 118.74(13) . . ? N1 C5 C16 122.9(3) . . ? N1 C5 H5A 118.5 . . ? C16 C5 H5A 118.5 . . ? C28 O6 Zn1 117.47(12) . . ? C1 C6 C16 119.3(3) . . ? C1 C6 H6A 120.3 . . ? C16 C6 H6A 120.3 . . ? C2 C7 C15 118.1(2) . . ? C2 C7 H7A 121.0 . . ? C15 C7 H7A 121.0 . . ? C34 C8 C2 119.1(2) . . ? C34 C8 H8A 120.5 . . ? C2 C8 H8A 120.5 . . ? C22 C9 C3 120.2(2) . . ? C22 C9 H9A 119.9 . . ? C3 C9 H9A 119.9 . . ? C18 C10 C17 119.9(2) . . ? C18 C10 H10A 120.0 . . ? C17 C10 H10A 120.0 . . ? C13 C11 C28 123.4(2) . . ? C13 C11 Cl4 118.72(17) . . ? C28 C11 Cl4 117.88(16) . . ? C19 C12 C14 118.5(2) . . ? C19 C12 H12A 120.7 . . ? C14 C12 H12A 120.7 . . ? C11 C13 C30 118.9(2) . . ? C11 C13 H13A 120.5 . . ? C30 C13 H13A 120.5 . . ? N4 C14 C12 122.5(2) . . ? N4 C14 H14A 118.7 . . ? C12 C14 H14A 118.7 . . ? N2 C15 C7 122.9(2) . . ? N2 C15 H15A 118.5 . . ? C7 C15 H15A 118.5 . . ? C6 C16 C5 118.6(3) . . ? C6 C16 H16A 120.7 . . ? C5 C16 H16A 120.7 . . ? C10 C17 C21 119.9(2) . . ? C10 C17 Cl2 118.67(18) . . ? C21 C17 Cl2 121.4(2) . . ? C10 C18 C31 123.3(2) . . ? C10 C18 Cl3 117.81(18) . . ? C31 C18 Cl3 118.93(18) . . ? C12 C19 C23 119.4(2) . . ? C12 C19 H19A 120.3 . . ? C23 C19 H19A 120.3 . . ? N1 C20 C1 121.0(2) . . ? N1 C20 C34 115.30(19) . . ? C1 C20 C34 123.7(2) . . ? C17 C21 C24 120.4(2) . . ? C17 C21 Cl1 118.64(18) . . ? C24 C21 Cl1 120.87(18) . . ? C9 C22 C26 118.3(2) . . ? C9 C22 H22A 120.9 . . ? C26 C22 H22A 120.9 . . ? C19 C23 C32 119.3(2) . . ? C19 C23 H23A 120.4 . . ? C32 C23 H23A 120.4 . . ? C21 C24 C31 121.2(2) . . ? C21 C24 C38 120.5(2) . . ? C31 C24 C38 118.28(18) . . ? C30 C25 C39 120.96(19) . . ? C30 C25 Cl6 117.85(16) . . ? C39 C25 Cl6 121.15(15) . . ? N3 C26 C22 121.4(2) . . ? N3 C26 C32 115.48(17) . . ? C22 C26 C32 123.1(2) . . ? N3 C27 C3 122.3(2) . . ? N3 C27 H27A 118.8 . . ? C3 C27 H27A 118.8 . . ? O6 C28 C11 119.41(18) . . ? O6 C28 C39 123.73(17) . . ? C11 C28 C39 116.84(18) . . ? C25 C30 C13 120.46(19) . . ? C25 C30 Cl5 122.15(17) . . ? C13 C30 Cl5 117.39(16) . . ? O5 C31 C18 121.4(2) . . ? O5 C31 C24 123.45(18) . . ? C18 C31 C24 115.09(19) . . ? N4 C32 C23 121.11(19) . . ? N4 C32 C26 115.21(18) . . ? C23 C32 C26 123.68(19) . . ? N2 C34 C8 121.2(2) . . ? N2 C34 C20 115.08(19) . . ? C8 C34 C20 123.7(2) . . ? O4 C36 O3 122.70(18) . . ? O4 C36 C39 120.06(18) . . ? O3 C36 C39 117.23(18) . . ? O1 C38 O2 124.3(2) . . ? O1 C38 C24 116.41(19) . . ? O2 C38 C24 119.32(19) . . ? C25 C39 C28 119.35(17) . . ? C25 C39 C36 122.63(18) . . ? C28 C39 C36 118.00(17) . . ? _diffrn_measured_fraction_theta_max 0.957 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.957 _refine_diff_density_max 0.315 _refine_diff_density_min -0.342 _refine_diff_density_rms 0.057 # Attachment '- Compound 3.cif' data_et3n_0m _database_code_depnum_ccdc_archive 'CCDC 774723' #TrackingRef '- Compound 3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H12 Cl3 N2 O4 Zn' _chemical_formula_weight 455.99 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.3392(8) _cell_length_b 10.5200(10) _cell_length_c 11.0835(11) _cell_angle_alpha 71.219(2) _cell_angle_beta 79.807(2) _cell_angle_gamma 75.307(2) _cell_volume 885.63(15) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 4873 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 27.42 _exptl_crystal_description Block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.710 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 458 _exptl_absorpt_coefficient_mu 1.862 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.809460 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ; SADABS v.2.03 (Bruker, 2001), R(int)=0.0313 before correction 2359 3164 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 APEX-2 CCD area detector' _diffrn_measurement_method '/w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_decay_% 0 _diffrn_reflns_number 11686 _diffrn_reflns_av_R_equivalents 0.0221 _diffrn_reflns_av_sigmaI/netI 0.0248 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 27.00 _reflns_number_total 3731 _reflns_number_gt 3118 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX-2' _computing_cell_refinement 'Bruker APEX-2' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0781P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3731 _refine_ls_number_parameters 228 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0484 _refine_ls_R_factor_gt 0.0385 _refine_ls_wR_factor_ref 0.1156 _refine_ls_wR_factor_gt 0.1093 _refine_ls_goodness_of_fit_ref 1.092 _refine_ls_restrained_S_all 1.092 _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 0.37957(3) 0.90306(3) 0.90526(3) 0.03462(13) Uani 1 1 d . . . Cl1 Cl -0.13116(9) 1.17838(9) 0.75801(8) 0.0537(2) Uani 1 1 d . . . Cl2 Cl 0.11147(18) 1.63723(10) 0.60168(12) 0.0921(4) Uani 1 1 d . . . Cl3 Cl 0.44159(13) 1.47215(9) 0.72642(9) 0.0673(3) Uani 1 1 d . . . O1 O 0.5244(2) 1.06141(19) 0.8609(2) 0.0410(4) Uani 1 1 d . . . N1 N 0.2322(3) 0.7563(2) 0.9442(2) 0.0399(5) Uani 1 1 d . . . C1 C 0.2976(3) 1.2516(3) 0.8053(3) 0.0364(6) Uani 1 1 d . . . O2 O 0.1857(2) 1.05017(19) 0.8639(2) 0.0438(5) Uani 1 1 d . . . C2 C 0.1744(3) 1.1802(3) 0.8087(3) 0.0359(6) Uani 1 1 d . . . O3 O 0.4677(2) 1.21765(19) 0.96646(19) 0.0405(4) Uani 1 1 d . . . C3 C 0.0284(3) 1.2606(3) 0.7498(3) 0.0409(6) Uani 1 1 d . . . N3 N 0.6792(4) 0.8801(3) 0.5635(3) 0.0613(8) Uani 1 1 d . . . O4 O 0.5070(3) 0.8473(2) 0.7471(2) 0.0535(6) Uani 1 1 d . . . C4 C 0.0111(4) 1.3979(3) 0.6892(3) 0.0512(8) Uani 1 1 d . . . H4A H -0.0865 1.4472 0.6524 0.061 Uiso 1 1 calc R . . C5 C 0.1353(5) 1.4635(3) 0.6822(3) 0.0522(8) Uani 1 1 d . . . C6 C 0.2801(4) 1.3906(3) 0.7411(3) 0.0439(7) Uani 1 1 d . . . C7 C 0.4425(3) 1.1718(3) 0.8806(3) 0.0343(6) Uani 1 1 d . . . C8 C 0.2953(4) 0.6244(3) 0.9963(4) 0.0570(9) Uani 1 1 d . . . H8A H 0.4037 0.6000 1.0188 0.068 Uiso 1 1 calc R . . C9 C 0.2107(4) 0.5220(3) 1.0192(4) 0.0577(9) Uani 1 1 d . . . H9A H 0.2619 0.4311 1.0556 0.069 Uiso 1 1 calc R . . C10 C 0.0486(3) 0.5539(3) 0.9879(3) 0.0386(6) Uani 1 1 d . . . C11 C -0.0194(4) 0.6925(3) 0.9369(3) 0.0455(7) Uani 1 1 d . . . H11A H -0.1290 0.7199 0.9167 0.055 Uiso 1 1 calc R . . C12 C 0.0740(4) 0.7892(3) 0.9161(3) 0.0449(7) Uani 1 1 d . . . H12A H 0.0258 0.8812 0.8811 0.054 Uiso 1 1 calc R . . C18 C 0.6124(4) 0.9060(4) 0.6712(3) 0.0562(8) Uani 1 1 d . . . H18A H 0.6461 0.9732 0.6924 0.067 Uiso 1 1 calc R . . C19 C 0.7991(5) 0.9543(5) 0.4773(4) 0.0821(12) Uani 1 1 d . . . H19A H 0.8095 1.0270 0.5083 0.123 Uiso 1 1 calc R . . H19B H 0.7619 0.9926 0.3934 0.123 Uiso 1 1 calc R . . H19C H 0.9054 0.8926 0.4732 0.123 Uiso 1 1 calc R . . C20 C 0.6366(6) 0.7737(5) 0.5270(4) 0.0800(12) Uani 1 1 d . . . H20A H 0.5236 0.7670 0.5599 0.120 Uiso 1 1 calc R . . H20B H 0.7100 0.6875 0.5615 0.120 Uiso 1 1 calc R . . H20C H 0.6478 0.7959 0.4352 0.120 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 0.03262(19) 0.0337(2) 0.0452(2) -0.01605(14) -0.00210(13) -0.01575(13) Cl1 0.0381(4) 0.0657(5) 0.0656(5) -0.0236(4) -0.0115(3) -0.0153(3) Cl2 0.1390(11) 0.0405(5) 0.0977(8) 0.0066(5) -0.0593(8) -0.0228(5) Cl3 0.0868(7) 0.0501(5) 0.0725(6) -0.0008(4) -0.0167(5) -0.0441(5) O1 0.0350(10) 0.0378(10) 0.0566(12) -0.0200(9) 0.0006(8) -0.0144(8) N1 0.0356(12) 0.0396(12) 0.0545(14) -0.0212(11) -0.0003(10) -0.0189(10) C1 0.0404(14) 0.0359(13) 0.0382(14) -0.0135(11) -0.0029(11) -0.0143(11) O2 0.0351(10) 0.0332(10) 0.0648(13) -0.0087(9) -0.0089(9) -0.0145(8) C2 0.0362(13) 0.0374(14) 0.0377(14) -0.0137(11) -0.0032(11) -0.0112(11) O3 0.0425(10) 0.0343(10) 0.0545(12) -0.0170(9) -0.0106(9) -0.0164(8) C3 0.0393(14) 0.0456(16) 0.0447(16) -0.0188(13) -0.0062(12) -0.0122(12) N3 0.0608(18) 0.0661(19) 0.0563(17) -0.0213(14) 0.0108(14) -0.0192(15) O4 0.0603(13) 0.0589(13) 0.0508(12) -0.0273(11) 0.0149(10) -0.0289(11) C4 0.0603(19) 0.0444(17) 0.0512(18) -0.0151(14) -0.0215(15) -0.0025(15) C5 0.078(2) 0.0341(15) 0.0458(17) -0.0061(13) -0.0207(16) -0.0112(15) C6 0.0600(18) 0.0365(14) 0.0425(16) -0.0117(12) -0.0057(13) -0.0223(13) C7 0.0325(12) 0.0333(13) 0.0425(15) -0.0110(11) -0.0001(11) -0.0191(11) C8 0.0343(15) 0.0364(16) 0.109(3) -0.0267(18) -0.0172(16) -0.0084(12) C9 0.0349(15) 0.0352(15) 0.113(3) -0.0285(17) -0.0152(16) -0.0101(12) C10 0.0367(13) 0.0392(14) 0.0512(16) -0.0231(12) 0.0006(12) -0.0186(12) C11 0.0386(15) 0.0435(16) 0.0622(19) -0.0120(14) -0.0140(13) -0.0209(13) C12 0.0431(15) 0.0393(15) 0.0553(18) -0.0052(13) -0.0122(13) -0.0202(12) C18 0.0546(19) 0.059(2) 0.062(2) -0.0271(17) -0.0002(16) -0.0158(16) C19 0.069(3) 0.090(3) 0.080(3) -0.022(2) 0.017(2) -0.026(2) C20 0.101(3) 0.080(3) 0.073(3) -0.044(2) 0.015(2) -0.031(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 Zn1 O2 1.9378(19) . ? Zn1 O3 1.979(2) 2_677 ? Zn1 O4 2.057(2) . ? Zn1 N1 2.104(2) . ? Zn1 O1 2.1816(19) . ? Cl1 C3 1.737(3) . ? Cl2 C5 1.733(3) . ? Cl3 C6 1.730(3) . ? O1 C7 1.253(3) . ? N1 C8 1.326(4) . ? N1 C12 1.342(4) . ? C1 C6 1.387(4) . ? C1 C2 1.407(4) . ? C1 C7 1.501(4) . ? O2 C2 1.292(3) . ? C2 C3 1.424(4) . ? O3 C7 1.265(3) . ? O3 Zn1 1.979(2) 2_677 ? C3 C4 1.365(4) . ? N3 C18 1.306(4) . ? N3 C20 1.445(5) . ? N3 C19 1.449(5) . ? O4 C18 1.242(4) . ? C4 C5 1.362(5) . ? C4 H4A 0.9300 . ? C5 C6 1.400(5) . ? C8 C9 1.367(4) . ? C8 H8A 0.9300 . ? C9 C10 1.386(4) . ? C9 H9A 0.9300 . ? C10 C11 1.390(4) . ? C10 C10 1.485(5) 2_567 ? C11 C12 1.373(4) . ? C11 H11A 0.9300 . ? C12 H12A 0.9300 . ? C18 H18A 0.9300 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? 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 O2 Zn1 O3 148.51(9) . 2_677 ? O2 Zn1 O4 112.68(10) . . ? O3 Zn1 O4 98.54(9) 2_677 . ? O2 Zn1 N1 90.43(9) . . ? O3 Zn1 N1 92.62(9) 2_677 . ? O4 Zn1 N1 91.82(9) . . ? O2 Zn1 O1 87.38(8) . . ? O3 Zn1 O1 89.60(8) 2_677 . ? O4 Zn1 O1 88.42(8) . . ? N1 Zn1 O1 177.71(8) . . ? C7 O1 Zn1 113.90(16) . . ? C8 N1 C12 116.9(2) . . ? C8 N1 Zn1 120.26(19) . . ? C12 N1 Zn1 122.8(2) . . ? C6 C1 C2 121.2(3) . . ? C6 C1 C7 122.1(2) . . ? C2 C1 C7 116.6(2) . . ? C2 O2 Zn1 130.52(17) . . ? O2 C2 C1 124.0(2) . . ? O2 C2 C3 119.9(2) . . ? C1 C2 C3 116.1(2) . . ? C7 O3 Zn1 118.53(17) . 2_677 ? C4 C3 C2 122.1(3) . . ? C4 C3 Cl1 120.1(2) . . ? C2 C3 Cl1 117.8(2) . . ? C18 N3 C20 120.5(3) . . ? C18 N3 C19 122.0(3) . . ? C20 N3 C19 117.5(3) . . ? C18 O4 Zn1 124.9(2) . . ? C5 C4 C3 120.7(3) . . ? C5 C4 H4A 119.7 . . ? C3 C4 H4A 119.7 . . ? C4 C5 C6 119.8(3) . . ? C4 C5 Cl2 119.6(3) . . ? C6 C5 Cl2 120.6(3) . . ? C1 C6 C5 120.0(3) . . ? C1 C6 Cl3 120.1(2) . . ? C5 C6 Cl3 119.8(2) . . ? O1 C7 O3 124.0(3) . . ? O1 C7 C1 119.2(2) . . ? O3 C7 C1 116.7(2) . . ? N1 C8 C9 123.9(3) . . ? N1 C8 H8A 118.0 . . ? C9 C8 H8A 118.0 . . ? C8 C9 C10 119.9(3) . . ? C8 C9 H9A 120.1 . . ? C10 C9 H9A 120.1 . . ? C9 C10 C11 116.2(2) . . ? C9 C10 C10 121.7(3) . 2_567 ? C11 C10 C10 122.0(3) . 2_567 ? C12 C11 C10 120.4(3) . . ? C12 C11 H11A 119.8 . . ? C10 C11 H11A 119.8 . . ? N1 C12 C11 122.6(3) . . ? N1 C12 H12A 118.7 . . ? C11 C12 H12A 118.7 . . ? O4 C18 N3 124.6(3) . . ? O4 C18 H18A 117.7 . . ? N3 C18 H18A 117.7 . . ? N3 C19 H19A 109.5 . . ? N3 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N3 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N3 C20 H20A 109.5 . . ? N3 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? N3 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.964 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.964 _refine_diff_density_max 0.877 _refine_diff_density_min -0.395 _refine_diff_density_rms 0.088 # Attachment '- Compound 4.cif' data_07rmd003_0m _database_code_depnum_ccdc_archive 'CCDC 774724' #TrackingRef '- Compound 4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H12 Cl6 N2 O6 Zn' _chemical_formula_weight 702.43 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' 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' Zn Zn 0.2839 1.4301 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 20.5213(11) _cell_length_b 9.4618(5) _cell_length_c 16.9888(9) _cell_angle_alpha 90.00 _cell_angle_beta 126.518(2) _cell_angle_gamma 90.00 _cell_volume 2651.1(2) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3335 _cell_measurement_theta_min 2.46 _cell_measurement_theta_max 25.41 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.760 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1400 _exptl_absorpt_coefficient_mu 1.576 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.722106 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ; SADABS v.2.03 (Bruker, 2001), R(int)=0.0617 before correction ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 APEX-2 CCD area detector' _diffrn_measurement_method '/w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_decay_% 0 _diffrn_reflns_number 18429 _diffrn_reflns_av_R_equivalents 0.0618 _diffrn_reflns_av_sigmaI/netI 0.0367 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.47 _diffrn_reflns_theta_max 26.48 _reflns_number_total 2733 _reflns_number_gt 2042 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX-2' _computing_cell_refinement 'Bruker APEX-2' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0595P)^2^+4.6145P] 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 2733 _refine_ls_number_parameters 177 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0705 _refine_ls_R_factor_gt 0.0436 _refine_ls_wR_factor_ref 0.1178 _refine_ls_wR_factor_gt 0.1002 _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_restrained_S_all 1.090 _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 0.0000 0.37195(6) 0.2500 0.02686(18) Uani 1 2 d S . . Cl1 Cl 0.22515(7) -0.20092(14) 0.16737(10) 0.0637(4) Uani 1 1 d . . . Cl2 Cl 0.02867(6) 0.12992(11) -0.14213(7) 0.0408(3) Uani 1 1 d . . . Cl3 Cl -0.00539(6) 0.31745(10) -0.02212(7) 0.0367(2) Uani 1 1 d . . . N1 N 0.09599(17) 0.5026(3) 0.3425(2) 0.0268(6) Uani 1 1 d . . . O1 O 0.01441(16) 0.2959(3) 0.15472(19) 0.0376(6) Uani 1 1 d . . . C1 C 0.08992(19) 0.1340(4) 0.1308(2) 0.0252(7) Uani 1 1 d . . . O2 O 0.10629(16) 0.1671(3) 0.28063(19) 0.0368(6) Uani 1 1 d . . . C2 C 0.1445(2) 0.0186(4) 0.1731(3) 0.0300(8) Uani 1 1 d . . . O3 O 0.18043(15) -0.0200(3) 0.26587(19) 0.0399(7) Uani 1 1 d . . . H3A H 0.1646 0.0310 0.2904 0.060 Uiso 1 1 calc R . . C3 C 0.1601(2) -0.0581(4) 0.1156(3) 0.0366(9) Uani 1 1 d . . . C4 C 0.1247(2) -0.0236(4) 0.0203(3) 0.0345(9) Uani 1 1 d . . . H4A H 0.1350 -0.0771 -0.0170 0.041 Uiso 1 1 calc R . . C5 C 0.0731(2) 0.0920(4) -0.0205(3) 0.0288(8) Uani 1 1 d . . . C6 C 0.0565(2) 0.1716(4) 0.0339(3) 0.0264(7) Uani 1 1 d . . . C7 C 0.0695(2) 0.2038(4) 0.1930(3) 0.0284(8) Uani 1 1 d . . . C8 C 0.1270(2) 0.5879(4) 0.3100(3) 0.0301(8) Uani 1 1 d . . . H8A H 0.1069 0.5820 0.2445 0.036 Uiso 1 1 calc R . . C9 C 0.1877(2) 0.6844(4) 0.3692(3) 0.0319(8) Uani 1 1 d . . . H9A H 0.2079 0.7411 0.3436 0.038 Uiso 1 1 calc R . . C10 C 0.21852(19) 0.6966(4) 0.4672(2) 0.0256(7) Uani 1 1 d . . . C11 C 0.1874(2) 0.6041(4) 0.5010(3) 0.0309(8) Uani 1 1 d . . . H11A H 0.2072 0.6056 0.5665 0.037 Uiso 1 1 calc R . . C12 C 0.1273(2) 0.5105(4) 0.4372(3) 0.0317(8) Uani 1 1 d . . . H12A H 0.1074 0.4497 0.4614 0.038 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 0.0279(3) 0.0287(3) 0.0237(3) 0.000 0.0152(3) 0.000 Cl1 0.0498(7) 0.0533(7) 0.0771(9) 0.0105(6) 0.0317(6) 0.0286(5) Cl2 0.0506(6) 0.0470(6) 0.0307(5) -0.0065(4) 0.0273(5) -0.0150(5) Cl3 0.0456(5) 0.0317(5) 0.0339(5) 0.0116(4) 0.0243(4) 0.0102(4) N1 0.0266(14) 0.0267(15) 0.0249(15) 0.0007(12) 0.0142(13) 0.0021(12) O1 0.0384(14) 0.0421(16) 0.0330(14) -0.0002(12) 0.0216(12) 0.0092(12) C1 0.0213(16) 0.0258(17) 0.0254(18) -0.0019(14) 0.0122(14) -0.0063(13) O2 0.0428(15) 0.0394(15) 0.0273(14) -0.0004(11) 0.0203(12) -0.0067(12) C2 0.0218(16) 0.0303(19) 0.0327(19) 0.0031(15) 0.0133(15) -0.0035(14) O3 0.0334(14) 0.0408(16) 0.0311(14) 0.0117(12) 0.0114(11) 0.0044(12) C3 0.0268(18) 0.031(2) 0.047(2) 0.0031(18) 0.0194(18) 0.0057(15) C4 0.0316(19) 0.032(2) 0.047(2) -0.0064(17) 0.0272(18) -0.0023(15) C5 0.0285(17) 0.0328(19) 0.0275(18) -0.0002(15) 0.0180(15) -0.0081(15) C6 0.0235(17) 0.0240(17) 0.0309(19) 0.0025(14) 0.0158(15) -0.0024(13) C7 0.0249(17) 0.0305(19) 0.0276(19) -0.0035(15) 0.0144(15) -0.0100(14) C8 0.039(2) 0.0285(19) 0.0259(18) 0.0015(14) 0.0214(16) 0.0008(15) C9 0.041(2) 0.0285(18) 0.034(2) 0.0017(16) 0.0263(18) -0.0018(16) C10 0.0203(16) 0.0271(18) 0.0274(18) 0.0061(14) 0.0132(14) 0.0078(13) C11 0.0263(17) 0.039(2) 0.0241(18) 0.0048(15) 0.0131(15) -0.0017(15) C12 0.0272(18) 0.039(2) 0.0266(18) 0.0042(15) 0.0146(15) -0.0043(15) _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 O1 1.948(3) 2 ? Zn1 O1 1.948(3) . ? Zn1 N1 2.048(3) . ? Zn1 N1 2.048(3) 2 ? Cl1 C3 1.728(4) . ? Cl2 C5 1.729(4) . ? Cl3 C6 1.728(3) . ? N1 C12 1.334(5) . ? N1 C8 1.335(5) . ? O1 C7 1.259(4) . ? C1 C6 1.400(5) . ? C1 C2 1.417(5) . ? C1 C7 1.504(5) . ? O2 C7 1.252(4) . ? C2 O3 1.333(4) . ? C2 C3 1.397(5) . ? O3 H3A 0.8200 . ? C3 C4 1.362(6) . ? C4 C5 1.387(5) . ? C4 H4A 0.9300 . ? C5 C6 1.383(5) . ? C8 C9 1.380(5) . ? C8 H8A 0.9300 . ? C9 C10 1.391(5) . ? C9 H9A 0.9300 . ? C10 C11 1.393(5) . ? C10 C10 1.489(7) 7_566 ? C11 C12 1.374(5) . ? C11 H11A 0.9300 . ? C12 H12A 0.9300 . ? 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 O1 Zn1 O1 136.66(17) 2 . ? O1 Zn1 N1 97.91(11) 2 . ? O1 Zn1 N1 107.95(12) . . ? O1 Zn1 N1 107.95(12) 2 2 ? O1 Zn1 N1 97.91(11) . 2 ? N1 Zn1 N1 105.74(16) . 2 ? C12 N1 C8 117.4(3) . . ? C12 N1 Zn1 120.8(2) . . ? C8 N1 Zn1 121.7(2) . . ? C7 O1 Zn1 111.0(2) . . ? C6 C1 C2 118.6(3) . . ? C6 C1 C7 124.7(3) . . ? C2 C1 C7 116.7(3) . . ? O3 C2 C3 119.3(3) . . ? O3 C2 C1 121.7(3) . . ? C3 C2 C1 119.1(3) . . ? C2 O3 H3A 109.5 . . ? C4 C3 C2 121.6(3) . . ? C4 C3 Cl1 119.7(3) . . ? C2 C3 Cl1 118.6(3) . . ? C3 C4 C5 119.4(4) . . ? C3 C4 H4A 120.3 . . ? C5 C4 H4A 120.3 . . ? C6 C5 C4 120.9(3) . . ? C6 C5 Cl2 121.4(3) . . ? C4 C5 Cl2 117.6(3) . . ? C5 C6 C1 120.2(3) . . ? C5 C6 Cl3 117.3(3) . . ? C1 C6 Cl3 122.4(3) . . ? O2 C7 O1 121.9(3) . . ? O2 C7 C1 119.4(3) . . ? O1 C7 C1 118.7(3) . . ? N1 C8 C9 123.0(3) . . ? N1 C8 H8A 118.5 . . ? C9 C8 H8A 118.5 . . ? C8 C9 C10 119.9(3) . . ? C8 C9 H9A 120.1 . . ? C10 C9 H9A 120.1 . . ? C9 C10 C11 116.6(3) . . ? C9 C10 C10 121.7(4) . 7_566 ? C11 C10 C10 121.7(4) . 7_566 ? C12 C11 C10 119.8(3) . . ? C12 C11 H11A 120.1 . . ? C10 C11 H11A 120.1 . . ? N1 C12 C11 123.3(3) . . ? N1 C12 H12A 118.4 . . ? C11 C12 H12A 118.4 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.099 _refine_diff_density_min -0.340 _refine_diff_density_rms 0.109 # Attachment '- Compound 5.cif' data_10ssg013_0m _database_code_depnum_ccdc_archive 'CCDC 774725' #TrackingRef '- Compound 5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H18 Cl6 N2 O6 Zn' _chemical_formula_weight 744.50 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' Zn Zn 0.2839 1.4301 '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 14.4957(5) _cell_length_b 8.8235(3) _cell_length_c 23.1793(8) _cell_angle_alpha 90.00 _cell_angle_beta 96.8080(10) _cell_angle_gamma 90.00 _cell_volume 2943.79(18) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 5831 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 26.12 _exptl_crystal_description Prism _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.680 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1496 _exptl_absorpt_coefficient_mu 1.425 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.748341 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS v.2.03 (Bruker, 2001), R(int)=0.0305 before correction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 APEX-2 CCD area detector' _diffrn_measurement_method '/w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_decay_% 0 _diffrn_reflns_number 37166 _diffrn_reflns_av_R_equivalents 0.0578 _diffrn_reflns_av_sigmaI/netI 0.0424 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 26.83 _reflns_number_total 6204 _reflns_number_gt 4758 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX-2' _computing_cell_refinement 'Bruker APEX-2' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0383P)^2^+2.6530P] 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 6204 _refine_ls_number_parameters 379 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0578 _refine_ls_R_factor_gt 0.0395 _refine_ls_wR_factor_ref 0.0972 _refine_ls_wR_factor_gt 0.0892 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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 0.26770(2) 0.55457(4) 0.055128(14) 0.02427(10) Uani 1 1 d . . . Cl1A Cl 0.51277(5) 1.34084(8) 0.04109(3) 0.03547(19) Uani 1 1 d . . . Cl1 Cl -0.04642(6) 0.80032(11) 0.29259(4) 0.0460(2) Uani 1 1 d . . . N1 N 0.28152(16) 0.3491(3) 0.09332(10) 0.0232(5) Uani 1 1 d . . . O1A O 0.37428(14) 0.6756(2) 0.08728(9) 0.0309(5) Uani 1 1 d . . . O1 O 0.14886(15) 0.6409(3) 0.07085(9) 0.0392(5) Uani 1 1 d . A . C1A C 0.44579(19) 0.9207(3) 0.08779(12) 0.0241(6) Uani 1 1 d . . . C1 C 0.0522(2) 0.7260(3) 0.14065(13) 0.0279(7) Uani 1 1 d . A . Cl2A Cl 0.65263(6) 0.99086(10) 0.21836(4) 0.0404(2) Uani 1 1 d . . . Cl2 Cl -0.17144(6) 0.97151(10) 0.07567(4) 0.0488(2) Uani 1 1 d . . . O2A O 0.31435(15) 0.8451(2) 0.02324(9) 0.0352(5) Uani 1 1 d . . . O2 O 0.19348(15) 0.5894(3) 0.16284(10) 0.0377(5) Uani 1 1 d . A . C2A C 0.5096(2) 0.8999(3) 0.13817(13) 0.0262(6) Uani 1 1 d . . . C2 C -0.0152(2) 0.7992(4) 0.10174(14) 0.0331(7) Uani 1 1 d . . . Cl3A Cl 0.50727(6) 0.74020(9) 0.18126(4) 0.0404(2) Uani 1 1 d . . . Cl3 Cl -0.00856(7) 0.80459(14) 0.02816(4) 0.0581(3) Uani 1 1 d . . . O3A O 0.38760(14) 1.0892(2) 0.00979(8) 0.0286(5) Uani 1 1 d . . . H3AA H 0.3512 1.0183 0.0036 0.043 Uiso 1 1 calc R . . O3 O 0.10714(14) 0.6679(2) 0.24001(9) 0.0332(5) Uani 1 1 d . A 2 H3A H 0.1484 0.6298 0.2234 0.050 Uiso 1 1 calc R A 2 C3A C 0.5742(2) 1.0112(3) 0.15601(13) 0.0288(7) Uani 1 1 d . . . C3 C -0.0893(2) 0.8737(3) 0.12240(15) 0.0345(7) Uani 1 1 d . . . C4A C 0.5765(2) 1.1454(3) 0.12522(13) 0.0293(7) Uani 1 1 d . . . H4AA H 0.6206 1.2192 0.1370 0.035 Uiso 1 1 calc R . . C4 C -0.0987(2) 0.8738(4) 0.18080(15) 0.0354(8) Uani 1 1 d . . . H4A H -0.1488 0.9228 0.1942 0.043 Uiso 1 1 calc R . . C5A C 0.5133(2) 1.1682(3) 0.07736(13) 0.0261(6) Uani 1 1 d . . . C5 C -0.0342(2) 0.8018(4) 0.21903(13) 0.0308(7) Uani 1 1 d . A . C6A C 0.4482(2) 1.0589(3) 0.05771(12) 0.0253(6) Uani 1 1 d . . . C6 C 0.0426(2) 0.7303(3) 0.20038(14) 0.0293(7) Uani 1 1 d . . . C7A C 0.3734(2) 0.8055(3) 0.06453(13) 0.0266(6) Uani 1 1 d . . . C7 C 0.1368(2) 0.6460(3) 0.12286(14) 0.0301(7) Uani 1 1 d . . . C8 C 0.2215(2) 0.2383(3) 0.07638(13) 0.0304(7) Uani 1 1 d . . . H8A H 0.1812 0.2517 0.0425 0.036 Uiso 1 1 calc R . . C9 C 0.2167(2) 0.1051(3) 0.10700(13) 0.0297(7) Uani 1 1 d . . . H9A H 0.1739 0.0309 0.0935 0.036 Uiso 1 1 calc R . . C10 C 0.2753(2) 0.0817(3) 0.15771(12) 0.0246(6) Uani 1 1 d . . . C11 C 0.3380(2) 0.1966(3) 0.17492(12) 0.0263(6) Uani 1 1 d . . . H11A H 0.3794 0.1858 0.2085 0.032 Uiso 1 1 calc R . . C12 C 0.3386(2) 0.3264(3) 0.14216(12) 0.0258(6) Uani 1 1 d . . . H12A H 0.3808 0.4022 0.1546 0.031 Uiso 1 1 calc R . . C13 C 0.2713(2) -0.0655(3) 0.19026(12) 0.0293(7) Uani 1 1 d . . . H13A H 0.3160 -0.1344 0.1765 0.035 Uiso 1 1 calc R . . H13B H 0.2102 -0.1093 0.1801 0.035 Uiso 1 1 calc R . . C14 C 0.2902(2) -0.0583(3) 0.25629(12) 0.0287(7) Uani 1 1 d . . . H14A H 0.3511 -0.0145 0.2672 0.034 Uiso 1 1 calc R . . H14B H 0.2907 -0.1604 0.2718 0.034 Uiso 1 1 calc R . . C15 C 0.2177(2) 0.0354(3) 0.28302(12) 0.0301(7) Uani 1 1 d . . . H15A H 0.2244 0.1412 0.2729 0.036 Uiso 1 1 calc R . . H15B H 0.1560 0.0027 0.2670 0.036 Uiso 1 1 calc R . . C16 C 0.2274(2) 0.0196(3) 0.34827(12) 0.0261(6) Uani 1 1 d . . . C17 C 0.1884(2) -0.1021(3) 0.37435(13) 0.0304(7) Uani 1 1 d . . . H17A H 0.1541 -0.1739 0.3516 0.036 Uiso 1 1 calc R . . C20 C 0.2781(2) 0.1222(3) 0.38450(13) 0.0281(7) Uani 1 1 d . . . H20A H 0.3057 0.2053 0.3688 0.034 Uiso 1 1 calc R . . C18 C 0.2003(2) -0.1167(3) 0.43377(13) 0.0292(7) Uani 1 1 d . . . H18A H 0.1734 -0.1989 0.4505 0.035 Uiso 1 1 calc R . . C19 C 0.2877(2) 0.1010(3) 0.44386(13) 0.0268(6) Uani 1 1 d . . . H19A H 0.3219 0.1712 0.4675 0.032 Uiso 1 1 calc R . . N2 N 0.24959(16) -0.0166(3) 0.46870(10) 0.0238(5) 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 0.03255(19) 0.02529(18) 0.01458(18) 0.00052(13) 0.00117(13) -0.00175(14) Cl1A 0.0419(4) 0.0277(4) 0.0377(5) 0.0097(3) 0.0085(4) -0.0017(3) Cl1 0.0442(5) 0.0633(6) 0.0313(5) -0.0110(4) 0.0077(4) 0.0018(4) N1 0.0291(12) 0.0247(12) 0.0155(12) -0.0004(10) 0.0016(10) -0.0020(10) O1A 0.0421(12) 0.0270(11) 0.0236(11) 0.0007(9) 0.0043(9) -0.0025(9) O1 0.0437(13) 0.0478(14) 0.0272(13) 0.0025(10) 0.0088(10) 0.0043(11) C1A 0.0286(15) 0.0219(15) 0.0230(16) -0.0031(12) 0.0081(12) 0.0006(11) C1 0.0278(15) 0.0247(15) 0.0310(18) -0.0020(13) 0.0026(13) -0.0031(12) Cl2A 0.0404(4) 0.0430(5) 0.0343(5) 0.0059(4) -0.0105(4) -0.0048(4) Cl2 0.0451(5) 0.0415(5) 0.0557(6) 0.0049(4) -0.0119(4) 0.0067(4) O2A 0.0402(12) 0.0292(12) 0.0334(13) -0.0002(10) -0.0077(10) -0.0011(10) O2 0.0403(13) 0.0412(13) 0.0310(13) -0.0001(10) 0.0020(10) 0.0087(10) C2A 0.0327(16) 0.0202(14) 0.0264(17) 0.0042(12) 0.0066(13) 0.0020(12) C2 0.0385(17) 0.0334(17) 0.0278(18) -0.0009(14) 0.0054(14) -0.0076(14) Cl3A 0.0476(5) 0.0337(4) 0.0362(5) 0.0130(3) -0.0107(4) -0.0052(4) Cl3 0.0518(6) 0.0917(8) 0.0298(5) 0.0146(5) 0.0004(4) 0.0156(5) O3A 0.0331(11) 0.0314(11) 0.0206(11) 0.0048(9) -0.0004(9) 0.0061(9) O3 0.0330(11) 0.0320(12) 0.0317(13) 0.0088(9) -0.0076(9) 0.0015(9) C3A 0.0308(16) 0.0331(16) 0.0219(17) 0.0013(13) 0.0005(13) 0.0006(13) C3 0.0341(17) 0.0263(16) 0.040(2) -0.0007(14) -0.0068(14) -0.0018(13) C4A 0.0283(15) 0.0262(16) 0.0333(18) -0.0011(13) 0.0040(13) -0.0052(12) C4 0.0295(16) 0.0352(18) 0.042(2) -0.0104(15) 0.0040(14) 0.0036(13) C5A 0.0330(16) 0.0204(14) 0.0267(16) 0.0045(12) 0.0108(13) 0.0020(12) C5 0.0313(16) 0.0338(17) 0.0277(17) -0.0059(13) 0.0057(13) -0.0021(13) C6A 0.0294(15) 0.0268(15) 0.0206(15) -0.0020(12) 0.0069(12) 0.0028(12) C6 0.0314(16) 0.0233(15) 0.0336(18) -0.0016(13) 0.0058(13) -0.0048(12) C7A 0.0328(16) 0.0265(16) 0.0217(16) -0.0034(12) 0.0076(13) 0.0048(12) C7 0.0326(16) 0.0258(16) 0.0314(18) -0.0019(13) 0.0013(14) -0.0039(13) C8 0.0362(17) 0.0322(17) 0.0218(16) 0.0009(13) -0.0014(13) -0.0035(13) C9 0.0368(17) 0.0290(16) 0.0230(17) -0.0026(12) 0.0025(13) -0.0104(13) C10 0.0347(15) 0.0250(15) 0.0155(15) -0.0026(11) 0.0084(12) -0.0005(12) C11 0.0345(16) 0.0291(15) 0.0142(15) -0.0003(12) -0.0012(12) 0.0004(13) C12 0.0316(15) 0.0237(15) 0.0220(16) -0.0047(12) 0.0029(12) -0.0040(12) C13 0.0438(18) 0.0265(15) 0.0185(15) -0.0018(12) 0.0076(13) -0.0030(13) C14 0.0412(17) 0.0242(15) 0.0213(16) 0.0037(12) 0.0058(13) 0.0033(13) C15 0.0412(17) 0.0336(17) 0.0157(15) 0.0042(12) 0.0036(13) 0.0057(13) C16 0.0337(16) 0.0268(15) 0.0177(15) 0.0015(12) 0.0020(12) 0.0062(12) C17 0.0435(18) 0.0299(16) 0.0169(16) -0.0031(12) -0.0007(13) -0.0076(13) C20 0.0383(17) 0.0248(15) 0.0218(16) 0.0036(12) 0.0060(13) -0.0020(13) C18 0.0396(17) 0.0271(16) 0.0202(16) 0.0001(12) 0.0013(13) -0.0068(13) C19 0.0325(16) 0.0242(15) 0.0233(16) -0.0026(12) 0.0017(13) -0.0016(12) N2 0.0304(13) 0.0248(12) 0.0161(12) -0.0015(10) 0.0021(10) 0.0005(10) _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 O1A 1.952(2) . ? Zn1 O1 1.957(2) . ? Zn1 N1 2.017(2) . ? Zn1 N2 2.017(2) 4_565 ? Cl1A C5A 1.740(3) . ? Cl1 C5 1.735(3) . ? N1 C12 1.335(4) . ? N1 C8 1.336(4) . ? O1A C7A 1.261(3) . ? O1 C7 1.239(4) . ? C1A C6A 1.407(4) . ? C1A C2A 1.413(4) . ? C1A C7A 1.514(4) . ? C1 C2 1.405(4) . ? C1 C6 1.408(4) . ? C1 C7 1.514(4) . ? Cl2A C3A 1.739(3) . ? Cl2 C3 1.740(3) . ? O2A C7A 1.255(4) . ? O2 C7 1.266(4) . ? C2A C3A 1.386(4) . ? C2A Cl3A 1.730(3) . ? C2 C3 1.393(4) . ? C2 Cl3 1.720(3) . ? O3A C6A 1.359(3) . ? O3A H3AA 0.8200 . ? O3 C6 1.348(4) . ? O3 H3A 0.8200 . ? C3A C4A 1.385(4) . ? C3 C4 1.376(5) . ? C4A C5A 1.367(4) . ? C4A H4AA 0.9300 . ? C4 C5 1.366(4) . ? C4 H4A 0.9300 . ? C5A C6A 1.387(4) . ? C5 C6 1.393(4) . ? C8 C9 1.380(4) . ? C8 H8A 0.9300 . ? C9 C10 1.382(4) . ? C9 H9A 0.9300 . ? C10 C11 1.389(4) . ? C10 C13 1.506(4) . ? C11 C12 1.375(4) . ? C11 H11A 0.9300 . ? C12 H12A 0.9300 . ? C13 C14 1.524(4) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.526(4) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.509(4) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C20 1.385(4) . ? C16 C17 1.385(4) . ? C17 C18 1.374(4) . ? C17 H17A 0.9300 . ? C20 C19 1.379(4) . ? C20 H20A 0.9300 . ? C18 N2 1.344(4) . ? C18 H18A 0.9300 . ? C19 N2 1.338(4) . ? C19 H19A 0.9300 . ? N2 Zn1 2.017(2) 4_566 ? 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 O1A Zn1 O1 112.97(9) . . ? O1A Zn1 N1 106.94(9) . . ? O1 Zn1 N1 108.17(9) . . ? O1A Zn1 N2 118.28(9) . 4_565 ? O1 Zn1 N2 103.64(9) . 4_565 ? N1 Zn1 N2 106.33(9) . 4_565 ? C12 N1 C8 117.1(2) . . ? C12 N1 Zn1 121.74(19) . . ? C8 N1 Zn1 120.1(2) . . ? C7A O1A Zn1 111.7(2) . . ? C7 O1 Zn1 115.1(2) . . ? C6A C1A C2A 118.0(3) . . ? C6A C1A C7A 117.5(3) . . ? C2A C1A C7A 124.4(3) . . ? C2 C1 C6 118.5(3) . . ? C2 C1 C7 124.3(3) . . ? C6 C1 C7 117.2(3) . . ? C3A C2A C1A 120.5(3) . . ? C3A C2A Cl3A 117.6(2) . . ? C1A C2A Cl3A 121.8(2) . . ? C3 C2 C1 120.2(3) . . ? C3 C2 Cl3 117.6(3) . . ? C1 C2 Cl3 122.2(2) . . ? C6A O3A H3AA 109.5 . . ? C6 O3 H3A 109.5 . . ? C4A C3A C2A 120.6(3) . . ? C4A C3A Cl2A 117.6(2) . . ? C2A C3A Cl2A 121.8(2) . . ? C4 C3 C2 120.5(3) . . ? C4 C3 Cl2 118.2(2) . . ? C2 C3 Cl2 121.3(3) . . ? C5A C4A C3A 119.3(3) . . ? C5A C4A H4AA 120.4 . . ? C3A C4A H4AA 120.4 . . ? C5 C4 C3 119.9(3) . . ? C5 C4 H4A 120.0 . . ? C3 C4 H4A 120.0 . . ? C4A C5A C6A 121.9(3) . . ? C4A C5A Cl1A 119.0(2) . . ? C6A C5A Cl1A 119.1(2) . . ? C4 C5 C6 121.3(3) . . ? C4 C5 Cl1 120.0(2) . . ? C6 C5 Cl1 118.7(2) . . ? O3A C6A C5A 118.7(3) . . ? O3A C6A C1A 121.6(3) . . ? C5A C6A C1A 119.7(3) . . ? O3 C6 C5 119.3(3) . . ? O3 C6 C1 121.2(3) . . ? C5 C6 C1 119.5(3) . . ? O2A C7A O1A 122.9(3) . . ? O2A C7A C1A 117.8(3) . . ? O1A C7A C1A 119.3(3) . . ? O1 C7 O2 122.9(3) . . ? O1 C7 C1 119.6(3) . . ? O2 C7 C1 117.4(3) . . ? N1 C8 C9 122.9(3) . . ? N1 C8 H8A 118.6 . . ? C9 C8 H8A 118.6 . . ? C8 C9 C10 120.1(3) . . ? C8 C9 H9A 119.9 . . ? C10 C9 H9A 119.9 . . ? C9 C10 C11 116.8(3) . . ? C9 C10 C13 120.0(3) . . ? C11 C10 C13 123.2(3) . . ? C12 C11 C10 119.8(3) . . ? C12 C11 H11A 120.1 . . ? C10 C11 H11A 120.1 . . ? N1 C12 C11 123.3(3) . . ? N1 C12 H12A 118.3 . . ? C11 C12 H12A 118.3 . . ? C10 C13 C14 117.0(2) . . ? C10 C13 H13A 108.0 . . ? C14 C13 H13A 108.0 . . ? C10 C13 H13B 108.0 . . ? C14 C13 H13B 108.0 . . ? H13A C13 H13B 107.3 . . ? C13 C14 C15 112.4(2) . . ? C13 C14 H14A 109.1 . . ? C15 C14 H14A 109.1 . . ? C13 C14 H14B 109.1 . . ? C15 C14 H14B 109.1 . . ? H14A C14 H14B 107.9 . . ? C16 C15 C14 111.7(2) . . ? C16 C15 H15A 109.3 . . ? C14 C15 H15A 109.3 . . ? C16 C15 H15B 109.3 . . ? C14 C15 H15B 109.3 . . ? H15A C15 H15B 107.9 . . ? C20 C16 C17 117.2(3) . . ? C20 C16 C15 121.8(3) . . ? C17 C16 C15 121.0(3) . . ? C18 C17 C16 120.1(3) . . ? C18 C17 H17A 120.0 . . ? C16 C17 H17A 120.0 . . ? C19 C20 C16 120.0(3) . . ? C19 C20 H20A 120.0 . . ? C16 C20 H20A 120.0 . . ? N2 C18 C17 122.5(3) . . ? N2 C18 H18A 118.8 . . ? C17 C18 H18A 118.8 . . ? N2 C19 C20 122.4(3) . . ? N2 C19 H19A 118.8 . . ? C20 C19 H19A 118.8 . . ? C19 N2 C18 117.9(2) . . ? C19 N2 Zn1 123.0(2) . 4_566 ? C18 N2 Zn1 119.10(19) . 4_566 ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 26.83 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.888 _refine_diff_density_min -0.519 _refine_diff_density_rms 0.078 # Attachment '- Compound 6.cif' data_10ssg014_0m _database_code_depnum_ccdc_archive 'CCDC 774726' #TrackingRef '- Compound 6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C54 H35 Cl12 N4 O12 Zn2' _chemical_formula_weight 1488.00 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' Cl Cl 0.1484 0.1585 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.8373(8) _cell_length_b 13.5119(9) _cell_length_c 18.5484(13) _cell_angle_alpha 90.00 _cell_angle_beta 106.514(2) _cell_angle_gamma 90.00 _cell_volume 2844.3(3) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2102 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 26.1 _exptl_crystal_description Cube _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.737 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1494 _exptl_absorpt_coefficient_mu 1.474 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.870010 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ; SADABS v.2.03 (Bruker, 2001), R(int)=0.0520 before correction ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 APEX-2 CCD area detector' _diffrn_measurement_method '/w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_decay_% 0 _diffrn_reflns_number 30375 _diffrn_reflns_av_R_equivalents 0.1185 _diffrn_reflns_av_sigmaI/netI 0.0794 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 24.11 _reflns_number_total 4527 _reflns_number_gt 2878 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX-2' _computing_cell_refinement 'Bruker APEX-2' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0770P)^2^+5.3771P] 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 4527 _refine_ls_number_parameters 377 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.1062 _refine_ls_R_factor_gt 0.0635 _refine_ls_wR_factor_ref 0.1817 _refine_ls_wR_factor_gt 0.1559 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.034 _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 0.40085(7) 0.11894(5) 0.18116(4) 0.0421(3) Uani 1 1 d . . . Cl1 Cl 0.1031(2) 0.12983(17) -0.10880(15) 0.0855(7) Uani 1 1 d . . . N1 N 0.4749(4) -0.0100(4) 0.1631(3) 0.0393(13) Uani 1 1 d . . . C1A C 0.4550(6) 0.1185(4) 0.4154(4) 0.0366(15) Uani 1 1 d . A 1 O1A O 0.3876(5) 0.1142(3) 0.2823(3) 0.0574(13) Uani 1 1 d . A 1 Cl1A Cl 0.2208(4) 0.1142(3) 0.3481(2) 0.0481(13) Uiso 0.50 1 d PD A 1 Cl1" Cl 0.6844(4) 0.1203(4) 0.4769(3) 0.0412(14) Uiso 0.50 1 d PD B 2 O1 O 0.2320(4) 0.1229(3) 0.1353(3) 0.0509(12) Uani 1 1 d . A . C1 C 0.0660(6) 0.1222(4) 0.0268(4) 0.0423(16) Uani 1 1 d . A . Cl2 Cl -0.1615(2) 0.12806(15) -0.18069(13) 0.0785(7) Uani 1 1 d . . . C2A C 0.3390(5) 0.1234(4) 0.4235(3) 0.0428(16) Uani 1 1 d D A 1 O2A O 0.5795(5) 0.1007(4) 0.3355(3) 0.0699(16) Uani 1 1 d . A 1 Cl2A Cl 0.18110(17) 0.14001(14) 0.50371(12) 0.0598(5) Uani 1 1 d . A 1 C2 C 0.0198(6) 0.1255(4) -0.0510(4) 0.0463(17) Uani 1 1 d . . . O2 O 0.2692(4) 0.1209(4) 0.0265(3) 0.0603(14) Uani 1 1 d . A . N2 N 0.4823(5) -0.7551(4) 0.1664(3) 0.0437(14) Uani 1 1 d . . . Cl3 Cl -0.2301(2) 0.11882(17) 0.09182(16) 0.0859(8) Uani 1 1 d . . . O3 O 0.0230(3) 0.1182(3) 0.1574(2) 0.0285(9) Uani 1 1 d . . . H3 H 0.0951 0.1189 0.1737 0.043 Uiso 1 1 calc R . . C3A C 0.3232(6) 0.1308(4) 0.4943(4) 0.0435(17) Uani 1 1 d . A 1 Cl3A Cl 0.64612(18) 0.13154(14) 0.63275(10) 0.0586(5) Uani 1 1 d . A 1 O3A O 0.6690(8) 0.1240(12) 0.4871(9) 0.065(6) Uiso 0.50 1 d PD A 1 H6A H 0.6777 0.1179 0.4451 0.097 Uiso 0.50 1 calc PR A 1 O3A' O 0.2335(6) 0.1398(6) 0.3624(4) 0.019(2) Uiso 0.50 1 d PD C 2 C3 C -0.1035(7) 0.1239(5) -0.0839(4) 0.0523(19) Uani 1 1 d . . . C4A C 0.4148(7) 0.1321(4) 0.5582(4) 0.0454(17) Uani 1 1 d . A 1 H4A H 0.4011 0.1361 0.6051 0.054 Uiso 1 1 calc R A 1 C4 C -0.1793(7) 0.1216(5) -0.0406(5) 0.057(2) Uani 1 1 d . . . H4 H -0.2603 0.1218 -0.0629 0.068 Uiso 1 1 calc R . . C5A C 0.5295(6) 0.1273(4) 0.5524(4) 0.0400(16) Uani 1 1 d . A 1 C5 C -0.1346(7) 0.1190(5) 0.0362(5) 0.055(2) Uani 1 1 d . . . C6A C 0.5466(5) 0.1218(4) 0.4819(4) 0.0399(15) Uani 1 1 d D A 1 C6 C -0.0118(6) 0.1206(5) 0.0732(5) 0.0524(19) Uani 1 1 d . . . C7A C 0.4765(7) 0.1099(4) 0.3404(4) 0.0423(17) Uani 1 1 d . A 1 C7 C 0.1977(6) 0.1225(4) 0.0629(4) 0.0398(15) Uani 1 1 d . . . C8 C 0.5253(6) -0.0249(5) 0.1078(4) 0.0458(17) Uani 1 1 d . . . H8 H 0.5270 0.0271 0.0753 0.055 Uiso 1 1 calc R A . C9 C 0.5746(6) -0.1137(5) 0.0972(4) 0.0487(18) Uani 1 1 d . A . H9 H 0.6100 -0.1208 0.0587 0.058 Uiso 1 1 calc R . . C10 C 0.5712(6) -0.1922(5) 0.1440(4) 0.0444(17) Uani 1 1 d . . . C11 C 0.5180(6) -0.1772(5) 0.2000(4) 0.0523(19) Uani 1 1 d . A . H11 H 0.5136 -0.2285 0.2325 0.063 Uiso 1 1 calc R . . C12 C 0.4711(6) -0.0856(5) 0.2076(4) 0.0490(18) Uani 1 1 d . . . H12 H 0.4353 -0.0767 0.2457 0.059 Uiso 1 1 calc R A . C13 C 0.6253(7) -0.2895(5) 0.1308(5) 0.060(2) Uani 1 1 d . A . H13B H 0.7100 -0.2842 0.1517 0.072 Uiso 1 1 calc R . . H13A H 0.6094 -0.2985 0.0770 0.072 Uiso 1 1 calc R . . C14 C 0.5852(6) -0.3823(5) 0.1628(4) 0.0442(16) Uani 1 1 d . . . H14A H 0.5003 -0.3883 0.1432 0.053 Uiso 1 1 calc R A . H14B H 0.6043 -0.3761 0.2170 0.053 Uiso 1 1 calc R . . C15 C 0.6426(7) -0.4754(5) 0.1435(5) 0.067(2) Uani 1 1 d . A . H15B H 0.6432 -0.4711 0.0914 0.080 Uiso 1 1 calc R . . H15A H 0.7240 -0.4770 0.1742 0.080 Uiso 1 1 calc R . . C16 C 0.5852(6) -0.5713(5) 0.1542(4) 0.0489(19) Uani 1 1 d . . . C17 C 0.4784(7) -0.5991(5) 0.1075(5) 0.071(3) Uani 1 1 d . A . H17 H 0.4377 -0.5556 0.0702 0.085 Uiso 1 1 calc R . . C18 C 0.4295(6) -0.6902(5) 0.1143(5) 0.060(2) Uani 1 1 d . . . H18 H 0.3570 -0.7065 0.0810 0.072 Uiso 1 1 calc R A . C19 C 0.5848(9) -0.7300(7) 0.2100(5) 0.102(4) Uani 1 1 d . . . H19 H 0.6242 -0.7753 0.2461 0.123 Uiso 1 1 calc R A . C20 C 0.6394(9) -0.6409(7) 0.2064(5) 0.094(4) Uani 1 1 d . A . H20 H 0.7131 -0.6278 0.2395 0.113 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 0.0425(5) 0.0393(5) 0.0490(5) 0.0011(4) 0.0201(4) -0.0038(4) Cl1 0.0916(17) 0.0760(15) 0.0859(17) 0.0095(13) 0.0206(14) -0.0134(13) N1 0.037(3) 0.041(3) 0.044(3) -0.001(3) 0.016(3) -0.007(2) C1A 0.042(4) 0.030(3) 0.045(4) 0.003(3) 0.024(3) 0.000(3) O1A 0.078(4) 0.057(3) 0.040(3) -0.005(2) 0.021(3) -0.002(3) O1 0.042(3) 0.050(3) 0.059(3) 0.000(3) 0.011(2) 0.004(2) C1 0.047(4) 0.023(3) 0.059(5) 0.004(3) 0.018(4) -0.001(3) Cl2 0.0753(15) 0.0621(13) 0.0791(15) 0.0135(11) -0.0086(12) -0.0034(11) C2A 0.054(4) 0.025(3) 0.051(4) 0.005(3) 0.017(3) 0.006(3) O2A 0.077(4) 0.070(4) 0.081(4) 0.014(3) 0.052(3) 0.017(3) Cl2A 0.0640(12) 0.0562(12) 0.0748(13) -0.0028(10) 0.0451(11) -0.0017(9) C2 0.051(4) 0.026(3) 0.060(5) 0.006(3) 0.013(4) 0.001(3) O2 0.054(3) 0.069(3) 0.067(3) -0.017(3) 0.033(3) -0.019(3) N2 0.038(3) 0.051(3) 0.045(4) 0.000(3) 0.015(3) -0.007(3) Cl3 0.0630(14) 0.0751(15) 0.138(2) 0.0148(14) 0.0583(15) 0.0105(11) O3 0.0192(19) 0.028(2) 0.041(2) -0.0154(19) 0.0122(17) -0.0031(17) C3A 0.054(4) 0.032(4) 0.054(5) -0.002(3) 0.029(4) 0.001(3) Cl3A 0.0734(13) 0.0534(11) 0.0449(11) 0.0008(9) 0.0102(9) -0.0169(10) C3 0.061(5) 0.026(4) 0.060(5) 0.008(3) 0.002(4) -0.006(3) C4A 0.072(5) 0.029(3) 0.043(4) 0.001(3) 0.029(4) -0.007(3) C4 0.053(5) 0.027(4) 0.090(6) 0.007(4) 0.019(5) 0.003(3) C5A 0.050(4) 0.029(3) 0.040(4) 0.005(3) 0.010(3) -0.008(3) C5 0.053(5) 0.035(4) 0.087(6) 0.013(4) 0.035(4) 0.002(4) C6A 0.048(4) 0.023(3) 0.051(4) 0.001(3) 0.018(3) -0.008(3) C6 0.048(4) 0.026(3) 0.090(6) 0.003(4) 0.031(4) 0.002(3) C7A 0.061(5) 0.024(3) 0.049(4) -0.001(3) 0.026(4) -0.003(3) C7 0.052(4) 0.025(3) 0.045(4) -0.004(3) 0.018(3) -0.004(3) C8 0.050(4) 0.051(4) 0.044(4) 0.000(3) 0.026(4) 0.001(3) C9 0.050(4) 0.051(4) 0.056(5) -0.005(4) 0.031(4) -0.008(4) C10 0.035(4) 0.048(4) 0.056(5) -0.010(3) 0.022(4) -0.008(3) C11 0.062(5) 0.040(4) 0.063(5) 0.003(4) 0.031(4) -0.006(4) C12 0.055(5) 0.045(4) 0.056(5) -0.001(4) 0.031(4) -0.002(3) C13 0.056(5) 0.049(4) 0.089(6) -0.012(4) 0.043(5) -0.006(4) C14 0.037(4) 0.042(4) 0.059(4) -0.012(3) 0.023(3) -0.007(3) C15 0.053(5) 0.043(4) 0.119(8) -0.016(4) 0.047(5) -0.010(4) C16 0.046(4) 0.040(4) 0.073(5) -0.020(4) 0.035(4) -0.013(3) C17 0.048(5) 0.045(5) 0.113(8) 0.025(4) 0.010(5) 0.002(4) C18 0.038(4) 0.043(4) 0.093(6) 0.000(4) 0.007(4) -0.008(3) C19 0.093(7) 0.105(8) 0.080(7) 0.046(6) -0.023(6) -0.053(6) C20 0.094(7) 0.091(7) 0.076(6) 0.021(6) -0.010(6) -0.058(6) _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 O1A 1.928(5) . ? Zn1 O1 1.938(5) . ? Zn1 N2 2.013(5) 1_565 ? Zn1 N1 2.021(5) . ? Cl1 C2 1.650(8) . ? N1 C12 1.322(8) . ? N1 C8 1.340(8) . ? C1A C6A 1.392(9) . ? C1A C2A 1.424(9) . ? C1A C7A 1.488(9) . ? O1A C7A 1.276(8) . ? Cl1A C2A 1.678(6) . ? O1 C7 1.287(8) . ? C1 C2 1.392(10) . ? C1 C6 1.429(10) . ? C1 C7 1.511(9) . ? Cl2 C3 1.730(8) . ? C2A C3A 1.382(9) . ? O2A C7A 1.254(8) . ? Cl2A C3A 1.744(7) . ? C2 C3 1.413(10) . ? O2 C7 1.224(8) . ? N2 C19 1.297(9) . ? N2 C18 1.323(9) . ? N2 Zn1 2.013(5) 1_545 ? Cl3 C5 1.733(8) . ? O3 C6 1.498(9) . ? O3 H3 0.8200 . ? C3A C4A 1.360(10) . ? Cl3A C5A 1.721(7) . ? O3A C6A 1.424(8) . ? O3A H6A 0.8200 . ? C3 C4 1.365(11) . ? C4A C5A 1.393(10) . ? C4A H4A 0.9300 . ? C4 C5 1.372(11) . ? C4 H4 0.9300 . ? C5A C6A 1.381(9) . ? C5 C6 1.420(11) . ? C8 C9 1.372(9) . ? C8 H8 0.9300 . ? C9 C10 1.378(9) . ? C9 H9 0.9300 . ? C10 C11 1.374(9) . ? C10 C13 1.512(9) . ? C11 C12 1.380(9) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.519(9) . ? C13 H13B 0.9700 . ? C13 H13A 0.9700 . ? C14 C15 1.520(9) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.502(9) . ? C15 H15B 0.9700 . ? C15 H15A 0.9700 . ? C16 C17 1.366(10) . ? C16 C20 1.371(11) . ? C17 C18 1.381(10) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 C20 1.377(11) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? 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 O1A Zn1 O1 94.0(2) . . ? O1A Zn1 N2 109.6(2) . 1_565 ? O1 Zn1 N2 113.0(2) . 1_565 ? O1A Zn1 N1 107.0(2) . . ? O1 Zn1 N1 113.2(2) . . ? N2 Zn1 N1 117.3(2) 1_565 . ? C12 N1 C8 117.6(6) . . ? C12 N1 Zn1 118.0(4) . . ? C8 N1 Zn1 124.4(4) . . ? C6A C1A C2A 115.9(5) . . ? C6A C1A C7A 122.2(6) . . ? C2A C1A C7A 121.9(6) . . ? C7A O1A Zn1 123.2(5) . . ? C7 O1 Zn1 116.0(4) . . ? C2 C1 C6 119.7(7) . . ? C2 C1 C7 120.7(6) . . ? C6 C1 C7 119.6(6) . . ? C3A C2A C1A 119.9(5) . . ? C3A C2A Cl1A 119.4(5) . . ? C1A C2A Cl1A 120.6(5) . . ? C1 C2 C3 120.0(7) . . ? C1 C2 Cl1 123.0(6) . . ? C3 C2 Cl1 117.0(6) . . ? C19 N2 C18 116.5(7) . . ? C19 N2 Zn1 122.4(5) . 1_545 ? C18 N2 Zn1 121.0(5) . 1_545 ? C6 O3 H3 109.5 . . ? C4A C3A C2A 122.6(6) . . ? C4A C3A Cl2A 117.7(5) . . ? C2A C3A Cl2A 119.7(5) . . ? C6A O3A H6A 109.5 . . ? C4 C3 C2 121.1(7) . . ? C4 C3 Cl2 118.5(6) . . ? C2 C3 Cl2 120.3(6) . . ? C3A C4A C5A 119.0(6) . . ? C3A C4A H4A 120.5 . . ? C5A C4A H4A 120.5 . . ? C3 C4 C5 119.2(7) . . ? C3 C4 H4 120.4 . . ? C5 C4 H4 120.4 . . ? C6A C5A C4A 119.0(6) . . ? C6A C5A Cl3A 121.6(5) . . ? C4A C5A Cl3A 119.4(5) . . ? C4 C5 C6 122.7(7) . . ? C4 C5 Cl3 119.6(6) . . ? C6 C5 Cl3 117.6(7) . . ? C5A C6A C1A 123.6(5) . . ? C5A C6A O3A 110.7(9) . . ? C1A C6A O3A 125.6(9) . . ? C5 C6 C1 117.1(7) . . ? C5 C6 O3 116.4(6) . . ? C1 C6 O3 126.5(6) . . ? O2A C7A O1A 122.0(6) . . ? O2A C7A C1A 120.3(7) . . ? O1A C7A C1A 117.8(6) . . ? O2 C7 O1 120.8(7) . . ? O2 C7 C1 122.9(6) . . ? O1 C7 C1 116.2(6) . . ? N1 C8 C9 122.7(6) . . ? N1 C8 H8 118.6 . . ? C9 C8 H8 118.6 . . ? C8 C9 C10 119.6(6) . . ? C8 C9 H9 120.2 . . ? C10 C9 H9 120.2 . . ? C11 C10 C9 117.6(6) . . ? C11 C10 C13 123.8(6) . . ? C9 C10 C13 118.6(6) . . ? C10 C11 C12 119.6(7) . . ? C10 C11 H11 120.2 . . ? C12 C11 H11 120.2 . . ? N1 C12 C11 122.9(6) . . ? N1 C12 H12 118.6 . . ? C11 C12 H12 118.6 . . ? C10 C13 C14 117.5(6) . . ? C10 C13 H13B 107.9 . . ? C14 C13 H13B 107.9 . . ? C10 C13 H13A 107.9 . . ? C14 C13 H13A 107.9 . . ? H13B C13 H13A 107.2 . . ? C13 C14 C15 112.4(6) . . ? C13 C14 H14A 109.1 . . ? C15 C14 H14A 109.1 . . ? C13 C14 H14B 109.1 . . ? C15 C14 H14B 109.1 . . ? H14A C14 H14B 107.9 . . ? C16 C15 C14 115.7(6) . . ? C16 C15 H15B 108.4 . . ? C14 C15 H15B 108.4 . . ? C16 C15 H15A 108.4 . . ? C14 C15 H15A 108.4 . . ? H15B C15 H15A 107.4 . . ? C17 C16 C20 115.0(7) . . ? C17 C16 C15 121.7(8) . . ? C20 C16 C15 123.1(7) . . ? C16 C17 C18 121.5(7) . . ? C16 C17 H17 119.2 . . ? C18 C17 H17 119.2 . . ? N2 C18 C17 122.3(7) . . ? N2 C18 H18 118.8 . . ? C17 C18 H18 118.8 . . ? N2 C19 C20 124.6(9) . . ? N2 C19 H19 117.7 . . ? C20 C19 H19 117.7 . . ? C16 C20 C19 120.1(8) . . ? C16 C20 H20 119.9 . . ? C19 C20 H20 119.9 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.11 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.746 _refine_diff_density_min -0.727 _refine_diff_density_rms 0.092 # Attachment '- Compound 7.cif' data_10ssg022_0m _database_code_depnum_ccdc_archive 'CCDC 774727' #TrackingRef '- Compound 7.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C52 H30 Cl12 N4 O14 Zn2' _chemical_formula_weight 1490.94 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' Zn Zn 0.2839 1.4301 '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 13.6683(5) _cell_length_b 13.6285(5) _cell_length_c 15.1486(6) _cell_angle_alpha 90.00 _cell_angle_beta 101.2170(10) _cell_angle_gamma 90.00 _cell_volume 2767.95(18) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 6889 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 26.2 _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.789 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1492 _exptl_absorpt_coefficient_mu 1.518 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.762074 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ; SADABS v.2.03 (Bruker, 2001), R(int)=0.0652 before correction ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 APEX-2 CCD area detector' _diffrn_measurement_method '/w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_decay_% 0 _diffrn_reflns_number 35396 _diffrn_reflns_av_R_equivalents 0.0522 _diffrn_reflns_av_sigmaI/netI 0.0418 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.52 _diffrn_reflns_theta_max 27.29 _reflns_number_total 6174 _reflns_number_gt 4713 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX-2' _computing_cell_refinement 'Bruker APEX-2' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0339P)^2^+4.1469P] 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 6174 _refine_ls_number_parameters 446 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0648 _refine_ls_R_factor_gt 0.0428 _refine_ls_wR_factor_ref 0.0997 _refine_ls_wR_factor_gt 0.0918 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _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 0.13028(3) 0.03911(3) 0.13466(2) 0.02612(11) Uani 1 1 d . . . Cl1A Cl 0.37814(7) 0.17413(6) 0.01058(5) 0.0396(2) Uani 1 1 d . . . Cl1 Cl -0.07639(8) 0.17680(7) 0.31177(6) 0.0492(2) Uani 1 1 d . . . O1A O 0.24236(16) 0.03184(16) 0.05368(13) 0.0315(5) Uani 1 1 d . A . O1 O 0.01371(16) 0.03227(17) 0.21366(14) 0.0338(5) Uani 1 1 d . A . N1 N 0.23827(18) 0.01860(18) 0.24718(16) 0.0252(5) Uani 1 1 d . A . C1A C 0.3321(2) -0.0089(2) -0.06228(19) 0.0272(7) Uani 1 1 d . A . C1 C -0.1393(2) -0.0110(2) 0.2606(2) 0.0316(7) Uani 1 1 d . A . O1WB O 0.0926(3) -0.0973(3) 0.0968(3) 0.0252(10) Uani 0.50 1 d P A 1 H1WA H 0.0393 -0.1112 0.1109 0.038 Uiso 0.50 1 calc PR A 1 O1WA O 0.0557(4) -0.0625(4) 0.0524(4) 0.0442(13) Uani 0.50 1 d P A 2 H1WB H 0.0908 -0.0823 0.0179 0.066 Uiso 0.50 1 calc PR A 2 Cl2A Cl 0.54983(7) 0.18221(6) -0.09280(5) 0.0400(2) Uani 1 1 d . . . Cl2 Cl -0.23508(7) 0.18128(8) 0.42879(7) 0.0574(3) Uani 1 1 d . . . C2A C 0.3942(2) 0.0750(2) -0.05495(19) 0.0288(7) Uani 1 1 d . . . C2 C -0.1498(2) 0.0739(3) 0.3118(2) 0.0349(8) Uani 1 1 d . . . O2A O 0.1906(2) -0.0951(2) -0.03497(17) 0.0516(7) Uani 1 1 d . A . O2 O -0.0698(2) -0.0988(2) 0.1538(2) 0.0745(11) Uani 1 1 d . A . N2 N 0.0958(19) 0.176(2) 0.0970(16) 0.045(6) Uani 0.50 1 d P A 1 N2' N 0.0894(15) 0.180(2) 0.0912(13) 0.023(4) Uiso 0.50 1 d P A 2 Cl3 Cl -0.36092(7) -0.17787(7) 0.31867(6) 0.0450(2) Uani 1 1 d . . . Cl3A Cl 0.45079(7) -0.16982(7) -0.23754(6) 0.0419(2) Uani 1 1 d . . . O3 O -0.20507(17) -0.17297(17) 0.21489(15) 0.0382(6) Uani 1 1 d . . . H3A H -0.1614 -0.1686 0.1848 0.057 Uiso 1 1 calc R . . O3A O 0.29516(16) -0.17118(15) -0.13326(13) 0.0300(5) Uani 1 1 d . . . H3AA H 0.2493 -0.1675 -0.1056 0.045 Uiso 1 1 calc R . . C3A C 0.4715(2) 0.0809(2) -0.1020(2) 0.0321(7) Uani 1 1 d . . . C3 C -0.2222(3) 0.0789(3) 0.3641(2) 0.0402(9) Uani 1 1 d . . . C4A C 0.4293(2) -0.0762(2) -0.1668(2) 0.0324(7) Uani 1 1 d . . . C4 C -0.2864(3) 0.0007(3) 0.3668(2) 0.0411(9) Uani 1 1 d . . . H4A H -0.3345 0.0041 0.4025 0.049 Uiso 1 1 calc R . . C5A C 0.4894(3) 0.0053(3) -0.1578(2) 0.0335(7) Uani 1 1 d . . . H5AA H 0.5417 0.0097 -0.1888 0.040 Uiso 1 1 calc R . . C5 C -0.2789(2) -0.0815(3) 0.3166(2) 0.0344(8) Uani 1 1 d . . . C6A C 0.3515(2) -0.0852(2) -0.12038(19) 0.0292(7) Uani 1 1 d . . . C6 C -0.2073(2) -0.0887(2) 0.2634(2) 0.0316(7) Uani 1 1 d . . . C7A C 0.2499(2) -0.0236(2) -0.0106(2) 0.0314(7) Uani 1 1 d . . . C7 C -0.0588(3) -0.0250(3) 0.2058(2) 0.0373(8) Uani 1 1 d . . . C8 C 0.2825(2) 0.0940(2) 0.2961(2) 0.0321(7) Uani 1 1 d . . . H8A H 0.2608 0.1573 0.2798 0.039 Uiso 1 1 calc R A . C9 C 0.3593(2) 0.0815(3) 0.3701(2) 0.0362(8) Uani 1 1 d . A . H9A H 0.3886 0.1358 0.4019 0.043 Uiso 1 1 calc R . . C10 C 0.3923(2) -0.0124(2) 0.3967(2) 0.0301(7) Uani 1 1 d . . . C11 C 0.3449(3) -0.0901(2) 0.3457(2) 0.0372(8) Uani 1 1 d . A . H11A H 0.3642 -0.1544 0.3609 0.045 Uiso 1 1 calc R . . C12 C 0.2695(3) -0.0720(2) 0.2729(2) 0.0364(8) Uani 1 1 d . . . H12A H 0.2389 -0.1251 0.2401 0.044 Uiso 1 1 calc R A . C13 C 0.4736(2) -0.0332(2) 0.4734(2) 0.0320(7) Uani 1 1 d . . . H13A H 0.4895 -0.0988 0.4858 0.048 Uiso 1 1 calc R . . C14 C 0.1490(12) 0.2202(14) 0.0288(14) 0.024(3) Uani 0.50 1 d P A 1 H14A H 0.1992 0.1845 0.0100 0.029 Uiso 0.50 1 calc PR A 1 C14' C 0.1232(11) 0.2295(17) 0.0428(14) 0.032(4) Uani 0.50 1 d P A 2 H14B H 0.1739 0.2018 0.0181 0.038 Uiso 0.50 1 calc PR A 2 C15 C 0.1254(9) 0.3128(9) -0.0070(7) 0.028(2) Uani 0.50 1 d P A 1 H15A H 0.1572 0.3380 -0.0510 0.033 Uiso 0.50 1 calc PR A 1 C15' C 0.0969(9) 0.3265(9) 0.0169(8) 0.030(3) Uani 0.50 1 d P A 2 H15B H 0.1293 0.3602 -0.0225 0.036 Uiso 0.50 1 calc PR A 2 C16 C 0.0530(8) 0.3675(9) 0.0242(7) 0.023(2) Uani 0.50 1 d P A 1 C16' C 0.0207(8) 0.3709(10) 0.0522(8) 0.031(2) Uani 0.50 1 d P A 2 C17 C 0.0018(10) 0.3222(12) 0.0841(8) 0.029(3) Uani 0.50 1 d P A 1 H17A H -0.0500 0.3541 0.1040 0.035 Uiso 0.50 1 calc PR A 1 C17' C -0.0189(12) 0.3189(14) 0.1138(9) 0.045(4) Uani 0.50 1 d P A 2 H17C H -0.0669 0.3474 0.1416 0.054 Uiso 0.50 1 calc PR A 2 C18 C 0.0293(13) 0.2315(14) 0.1123(8) 0.033(3) Uani 0.50 1 d P A 1 H18A H -0.0090 0.2049 0.1508 0.040 Uiso 0.50 1 calc PR A 1 C18' C 0.0129(13) 0.2228(12) 0.1351(9) 0.031(3) Uani 0.50 1 d P A 2 H18B H -0.0142 0.1865 0.1765 0.037 Uiso 0.50 1 calc PR A 2 C19 C 0.0321(6) 0.4679(6) -0.0118(6) 0.0281(14) Uani 0.50 1 d P . 1 H19A H 0.0672 0.4883 -0.0553 0.042 Uiso 0.50 1 calc PR . 1 C19' C -0.0146(7) 0.4727(8) 0.0292(6) 0.0383(17) Uani 0.50 1 d P . 2 H19D H -0.0615 0.4985 0.0597 0.057 Uiso 0.50 1 calc PR . 2 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 0.02727(19) 0.02285(18) 0.02554(18) -0.00033(14) -0.00151(13) 0.00005(15) Cl1A 0.0506(5) 0.0337(4) 0.0340(4) -0.0058(3) 0.0072(4) -0.0092(4) Cl1 0.0581(6) 0.0427(5) 0.0444(5) -0.0159(4) 0.0040(4) -0.0068(4) O1A 0.0404(13) 0.0292(12) 0.0251(11) -0.0031(9) 0.0066(9) -0.0077(10) O1 0.0283(12) 0.0358(13) 0.0350(12) -0.0066(10) 0.0004(9) -0.0018(10) N1 0.0257(13) 0.0250(14) 0.0234(12) 0.0024(10) 0.0016(10) 0.0014(10) C1A 0.0349(18) 0.0255(16) 0.0192(13) 0.0024(12) 0.0002(12) -0.0036(13) C1 0.0337(18) 0.0342(18) 0.0252(15) -0.0030(13) 0.0015(13) -0.0006(14) O1WB 0.028(2) 0.022(2) 0.023(2) 0.0041(18) -0.0017(18) -0.0009(18) O1WA 0.043(3) 0.047(3) 0.044(3) -0.015(3) 0.010(3) -0.016(3) Cl2A 0.0435(5) 0.0386(5) 0.0353(4) 0.0096(4) 0.0010(4) -0.0121(4) Cl2 0.0430(5) 0.0720(7) 0.0520(6) -0.0299(5) -0.0034(4) 0.0158(5) C2A 0.0360(18) 0.0270(16) 0.0204(14) 0.0016(12) -0.0022(12) -0.0014(13) C2 0.0361(19) 0.0371(19) 0.0278(16) -0.0006(14) -0.0029(14) 0.0016(15) O2A 0.0612(17) 0.0531(17) 0.0455(14) -0.0230(13) 0.0228(13) -0.0299(14) O2 0.089(2) 0.067(2) 0.085(2) -0.0497(18) 0.0580(19) -0.0487(18) N2 0.048(8) 0.026(6) 0.047(8) 0.002(4) -0.028(5) 0.007(4) Cl3 0.0358(5) 0.0550(6) 0.0433(5) 0.0154(4) 0.0052(4) -0.0038(4) Cl3A 0.0443(5) 0.0461(5) 0.0344(4) -0.0097(4) 0.0053(4) 0.0085(4) O3 0.0389(14) 0.0384(14) 0.0387(13) 0.0003(11) 0.0114(11) -0.0048(11) O3A 0.0355(12) 0.0314(12) 0.0225(10) -0.0039(9) 0.0040(9) 0.0002(10) C3A 0.0355(18) 0.0325(17) 0.0247(15) 0.0069(13) -0.0030(13) -0.0058(14) C3 0.0310(18) 0.053(2) 0.0324(17) -0.0101(16) -0.0050(14) 0.0117(17) C4A 0.0382(19) 0.0340(18) 0.0226(15) -0.0001(13) -0.0004(13) 0.0061(15) C4 0.0285(18) 0.063(2) 0.0301(17) 0.0001(17) 0.0022(14) 0.0097(17) C5A 0.0351(19) 0.044(2) 0.0209(15) 0.0032(13) 0.0029(13) 0.0006(15) C5 0.0285(17) 0.045(2) 0.0273(16) 0.0076(15) -0.0009(13) 0.0011(15) C6A 0.0348(18) 0.0286(17) 0.0214(14) 0.0018(12) -0.0019(13) -0.0013(13) C6 0.0326(18) 0.0323(18) 0.0276(15) 0.0015(13) 0.0001(13) 0.0025(14) C7A 0.0392(19) 0.0299(18) 0.0233(15) -0.0020(13) 0.0016(13) -0.0031(14) C7 0.044(2) 0.037(2) 0.0304(17) -0.0054(14) 0.0050(14) -0.0065(16) C8 0.0335(18) 0.0260(17) 0.0339(17) 0.0000(13) -0.0008(14) 0.0025(14) C9 0.0348(19) 0.0334(18) 0.0354(17) -0.0069(15) -0.0052(14) -0.0022(15) C10 0.0255(16) 0.0384(19) 0.0258(15) 0.0014(13) 0.0036(12) 0.0016(13) C11 0.042(2) 0.0272(18) 0.0360(18) -0.0001(14) -0.0077(15) 0.0073(15) C12 0.0403(19) 0.0272(17) 0.0360(17) -0.0013(14) -0.0068(15) -0.0010(14) C13 0.0323(17) 0.0363(19) 0.0261(15) 0.0030(13) 0.0028(13) 0.0033(14) C14 0.011(7) 0.022(6) 0.040(6) 0.008(4) 0.009(4) 0.003(4) C14' 0.010(8) 0.037(6) 0.046(8) -0.003(5) 0.000(6) 0.010(6) C15 0.030(6) 0.027(5) 0.027(5) 0.001(4) 0.008(3) 0.006(4) C15' 0.032(8) 0.031(6) 0.028(6) -0.002(5) 0.006(4) 0.004(5) C16 0.021(6) 0.023(5) 0.025(5) -0.004(4) 0.005(4) 0.003(5) C16' 0.024(6) 0.026(5) 0.041(7) -0.007(5) 0.000(4) 0.011(5) C17 0.036(6) 0.027(5) 0.024(6) -0.002(6) 0.003(4) 0.016(5) C17' 0.055(8) 0.040(6) 0.040(8) 0.000(6) 0.012(5) 0.026(5) C18 0.043(7) 0.048(6) 0.011(5) 0.008(5) 0.010(4) -0.013(5) C18' 0.038(6) 0.027(5) 0.034(7) 0.011(4) 0.021(5) 0.018(4) C19 0.028(4) 0.024(4) 0.032(4) 0.004(3) 0.005(3) 0.007(3) C19' 0.026(4) 0.039(6) 0.048(5) -0.001(4) 0.003(4) 0.003(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 N2 1.98(3) . ? Zn1 O1WB 1.985(4) . ? Zn1 O1WA 2.005(5) . ? Zn1 N1 2.045(2) . ? Zn1 N2' 2.07(3) . ? Zn1 O1A 2.143(2) . ? Zn1 O1 2.173(2) . ? Cl1A C2A 1.715(3) . ? Cl1 C2 1.725(4) . ? O1A C7A 1.252(4) . ? O1 C7 1.249(4) . ? N1 C12 1.339(4) . ? N1 C8 1.340(4) . ? C1A C2A 1.416(4) . ? C1A C6A 1.420(4) . ? C1A C7A 1.503(5) . ? C1 C2 1.416(5) . ? C1 C6 1.416(5) . ? C1 C7 1.514(5) . ? O1WB H1WA 0.8200 . ? O1WA H1WB 0.8200 . ? Cl2A C3A 1.736(3) . ? Cl2 C3 1.733(4) . ? C2A C3A 1.388(5) . ? C2 C3 1.384(5) . ? O2A C7A 1.275(4) . ? O2 C7 1.269(4) . ? N2 C18 1.24(3) . ? N2 C14 1.50(4) . ? N2' C14' 1.16(4) . ? N2' C18' 1.46(2) . ? Cl3 C5 1.732(4) . ? Cl3A C4A 1.728(3) . ? O3 C6 1.367(4) . ? O3 H3A 0.8200 . ? O3A C6A 1.395(4) . ? O3A H3AA 0.8200 . ? C3A C5A 1.384(5) . ? C3 C4 1.386(5) . ? C4A C5A 1.373(5) . ? C4A C6A 1.390(5) . ? C4 C5 1.369(5) . ? C4 H4A 0.9300 . ? C5A H5AA 0.9300 . ? C5 C6 1.386(5) . ? C8 C9 1.390(4) . ? C8 H8A 0.9300 . ? C9 C10 1.390(5) . ? C9 H9A 0.9300 . ? C10 C11 1.394(5) . ? C10 C13 1.471(4) . ? C11 C12 1.378(4) . ? C11 H11A 0.9300 . ? C12 H12A 0.9300 . ? C13 C13 1.329(6) 3_656 ? C13 H13A 0.9300 . ? C14 C15 1.39(2) . ? C14 H14A 0.9300 . ? C14' C15' 1.41(3) . ? C14' H14B 0.9300 . ? C15 C16 1.392(12) . ? C15 H15A 0.9300 . ? C15' C16' 1.397(13) . ? C15' H15B 0.9300 . ? C16 C17 1.393(14) . ? C16 C19 1.480(16) . ? C16' C17' 1.366(16) . ? C16' C19' 1.487(18) . ? C17 C18 1.34(3) . ? C17 H17A 0.9300 . ? C17' C18' 1.40(3) . ? C17' H17C 0.9300 . ? C18 H18A 0.9300 . ? C18' H18B 0.9300 . ? C19 C19 1.337(15) 3_565 ? C19 H19A 0.9300 . ? C19' C19' 1.278(17) 3_565 ? C19' H19D 0.9300 . ? 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 N2 Zn1 O1WB 140.0(7) . . ? N2 Zn1 O1WA 114.1(7) . . ? O1WB Zn1 O1WA 25.91(17) . . ? N2 Zn1 N1 117.5(7) . . ? O1WB Zn1 N1 102.57(14) . . ? O1WA Zn1 N1 128.41(19) . . ? N2 Zn1 N2' 2.4(13) . . ? O1WB Zn1 N2' 137.6(6) . . ? O1WA Zn1 N2' 111.7(6) . . ? N1 Zn1 N2' 119.9(6) . . ? N2 Zn1 O1A 92.0(8) . . ? O1WB Zn1 O1A 88.01(14) . . ? O1WA Zn1 O1A 86.90(16) . . ? N1 Zn1 O1A 89.44(9) . . ? N2' Zn1 O1A 92.3(5) . . ? N2 Zn1 O1 92.3(8) . . ? O1WB Zn1 O1 86.69(14) . . ? O1WA Zn1 O1 88.51(16) . . ? N1 Zn1 O1 91.31(9) . . ? N2' Zn1 O1 91.9(5) . . ? O1A Zn1 O1 174.68(8) . . ? C7A O1A Zn1 130.4(2) . . ? C7 O1 Zn1 128.9(2) . . ? C12 N1 C8 117.5(3) . . ? C12 N1 Zn1 120.4(2) . . ? C8 N1 Zn1 122.0(2) . . ? C2A C1A C6A 117.3(3) . . ? C2A C1A C7A 124.4(3) . . ? C6A C1A C7A 118.3(3) . . ? C2 C1 C6 117.2(3) . . ? C2 C1 C7 124.4(3) . . ? C6 C1 C7 118.3(3) . . ? Zn1 O1WB H1WA 109.5 . . ? Zn1 O1WA H1WB 109.5 . . ? C3A C2A C1A 120.8(3) . . ? C3A C2A Cl1A 116.6(2) . . ? C1A C2A Cl1A 122.6(3) . . ? C3 C2 C1 120.9(3) . . ? C3 C2 Cl1 116.2(3) . . ? C1 C2 Cl1 122.9(3) . . ? C18 N2 C14 111(2) . . ? C18 N2 Zn1 132(2) . . ? C14 N2 Zn1 117.1(17) . . ? C14' N2' C18' 118(2) . . ? C14' N2' Zn1 128.8(17) . . ? C18' N2' Zn1 113.4(13) . . ? C6 O3 H3A 109.5 . . ? C6A O3A H3AA 109.5 . . ? C5A C3A C2A 120.9(3) . . ? C5A C3A Cl2A 117.5(3) . . ? C2A C3A Cl2A 121.6(3) . . ? C2 C3 C4 120.4(3) . . ? C2 C3 Cl2 121.7(3) . . ? C4 C3 Cl2 117.9(3) . . ? C5A C4A C6A 121.6(3) . . ? C5A C4A Cl3A 119.2(3) . . ? C6A C4A Cl3A 119.2(3) . . ? C5 C4 C3 119.7(3) . . ? C5 C4 H4A 120.1 . . ? C3 C4 H4A 120.1 . . ? C4A C5A C3A 119.3(3) . . ? C4A C5A H5AA 120.4 . . ? C3A C5A H5AA 120.4 . . ? C4 C5 C6 121.3(3) . . ? C4 C5 Cl3 119.5(3) . . ? C6 C5 Cl3 119.3(3) . . ? C4A C6A O3A 117.3(3) . . ? C4A C6A C1A 120.2(3) . . ? O3A C6A C1A 122.5(3) . . ? O3 C6 C5 117.7(3) . . ? O3 C6 C1 121.9(3) . . ? C5 C6 C1 120.4(3) . . ? O1A C7A O2A 122.9(3) . . ? O1A C7A C1A 120.5(3) . . ? O2A C7A C1A 116.6(3) . . ? O1 C7 O2 123.4(3) . . ? O1 C7 C1 121.2(3) . . ? O2 C7 C1 115.4(3) . . ? N1 C8 C9 122.7(3) . . ? N1 C8 H8A 118.6 . . ? C9 C8 H8A 118.6 . . ? C10 C9 C8 119.9(3) . . ? C10 C9 H9A 120.1 . . ? C8 C9 H9A 120.1 . . ? C9 C10 C11 116.7(3) . . ? C9 C10 C13 124.0(3) . . ? C11 C10 C13 119.3(3) . . ? C12 C11 C10 120.1(3) . . ? C12 C11 H11A 119.9 . . ? C10 C11 H11A 119.9 . . ? N1 C12 C11 123.0(3) . . ? N1 C12 H12A 118.5 . . ? C11 C12 H12A 118.5 . . ? C13 C13 C10 125.8(4) 3_656 . ? C13 C13 H13A 117.1 3_656 . ? C10 C13 H13A 117.1 . . ? C15 C14 N2 121.8(14) . . ? C15 C14 H14A 119.1 . . ? N2 C14 H14A 119.1 . . ? N2' C14' C15' 127.9(15) . . ? N2' C14' H14B 116.0 . . ? C15' C14' H14B 116.0 . . ? C14 C15 C16 118.7(11) . . ? C14 C15 H15A 120.6 . . ? C16 C15 H15A 120.6 . . ? C16' C15' C14' 118.0(11) . . ? C16' C15' H15B 121.0 . . ? C14' C15' H15B 121.0 . . ? C15 C16 C17 117.7(10) . . ? C15 C16 C19 117.9(10) . . ? C17 C16 C19 124.4(11) . . ? C17' C16' C15' 117.5(10) . . ? C17' C16' C19' 119.4(11) . . ? C15' C16' C19' 123.1(12) . . ? C18 C17 C16 118.2(12) . . ? C18 C17 H17A 120.9 . . ? C16 C17 H17A 120.9 . . ? C16' C17' C18' 119.8(11) . . ? C16' C17' H17C 120.1 . . ? C18' C17' H17C 120.1 . . ? N2 C18 C17 132.5(17) . . ? N2 C18 H18A 113.7 . . ? C17 C18 H18A 113.7 . . ? C17' C18' N2' 119.1(15) . . ? C17' C18' H18B 120.5 . . ? N2' C18' H18B 120.5 . . ? C19 C19 C16 126.6(14) 3_565 . ? C19 C19 H19A 116.7 3_565 . ? C16 C19 H19A 116.7 . . ? C19' C19' C16' 125.1(17) 3_565 . ? C19' C19' H19D 117.4 3_565 . ? C16' C19' H19D 117.4 . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.29 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.483 _refine_diff_density_min -0.447 _refine_diff_density_rms 0.077 # Attachment '- compound 8.cif' data_ssg _database_code_depnum_ccdc_archive 'CCDC 774728' #TrackingRef '- compound 8.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H9 Cl3 N2 O3 Zn' _chemical_formula_weight 460.98 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.2531(7) _cell_length_b 10.6582(10) _cell_length_c 12.4388(11) _cell_angle_alpha 73.757(2) _cell_angle_beta 73.122(2) _cell_angle_gamma 76.445(2) _cell_volume 991.16(15) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 4502 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 29.48 _exptl_crystal_description Block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.545 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 460 _exptl_absorpt_coefficient_mu 1.661 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.773746 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS v.2.03 (Bruker, 2001), R(int)=0.0865 before correction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 APEX-2 CCD area detector' _diffrn_measurement_method '/w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_decay_% 0 _diffrn_reflns_number 11055 _diffrn_reflns_av_R_equivalents 0.0384 _diffrn_reflns_av_sigmaI/netI 0.0501 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 28.00 _reflns_number_total 4527 _reflns_number_gt 3834 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX-2' _computing_cell_refinement 'Bruker APEX-2' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0326P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4527 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0370 _refine_ls_R_factor_gt 0.0312 _refine_ls_wR_factor_ref 0.0789 _refine_ls_wR_factor_gt 0.0765 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 0.66942(3) 0.64856(2) 0.401694(19) 0.01742(8) Uani 1 1 d . . . Cl1 Cl 0.67064(7) 0.17596(5) 0.26784(5) 0.03085(14) Uani 1 1 d . . . Cl2 Cl 1.05759(9) 0.07155(6) 0.16081(6) 0.04583(18) Uani 1 1 d . . . Cl3 Cl 1.24893(7) 0.44519(6) 0.28942(5) 0.03309(14) Uani 1 1 d . . . O1 O 0.53858(17) 0.50758(13) 0.37830(12) 0.0191(3) Uani 1 1 d . . . N1 N 0.6123(2) 0.77869(16) 0.25031(14) 0.0203(4) Uani 1 1 d . . . C1 C 0.7895(3) 0.35020(19) 0.33471(16) 0.0184(4) Uani 1 1 d . . . N2 N 0.7977(2) 0.77483(16) 0.44139(14) 0.0193(4) Uani 1 1 d . . . C2 C 0.8327(3) 0.2461(2) 0.27983(17) 0.0221(4) Uani 1 1 d . . . O2 O 0.54568(17) 0.29970(13) 0.48275(12) 0.0200(3) Uani 1 1 d . . . O3 O 0.88151(18) 0.52235(14) 0.37966(13) 0.0239(3) Uani 1 1 d . . . C3 C 1.0024(3) 0.2020(2) 0.22973(18) 0.0262(5) Uani 1 1 d . . . C4 C 1.1297(3) 0.2631(2) 0.23450(18) 0.0274(5) Uani 1 1 d . . . H4A H 1.2442 0.2321 0.2034 0.033 Uiso 1 1 calc R . . C5 C 1.0880(3) 0.3693(2) 0.28492(18) 0.0222(4) Uani 1 1 d . . . C6 C 0.9162(3) 0.4206(2) 0.33414(17) 0.0198(4) Uani 1 1 d . . . C7 C 0.6106(2) 0.38963(19) 0.40211(16) 0.0167(4) Uani 1 1 d . . . C8 C 0.4889(3) 0.7630(2) 0.2093(2) 0.0369(6) Uani 1 1 d . . . H8A H 0.4311 0.6919 0.2477 0.044 Uiso 1 1 calc R . . C9 C 0.4415(3) 0.8464(3) 0.1126(2) 0.0430(7) Uani 1 1 d . . . H9A H 0.3537 0.8305 0.0879 0.052 Uiso 1 1 calc R . . C10 C 0.5236(3) 0.9539(2) 0.05189(17) 0.0226(4) Uani 1 1 d . . . C11 C 0.6519(3) 0.9708(2) 0.09565(18) 0.0284(5) Uani 1 1 d . . . H11A H 0.7110 1.0415 0.0595 0.034 Uiso 1 1 calc R . . C12 C 0.6915(3) 0.8822(2) 0.19297(18) 0.0276(5) Uani 1 1 d . . . H12A H 0.7785 0.8956 0.2201 0.033 Uiso 1 1 calc R . . C13 C 0.9688(3) 0.7600(2) 0.42034(18) 0.0231(4) Uani 1 1 d . . . H13A H 1.0349 0.6890 0.3895 0.028 Uiso 1 1 calc R . . C14 C 1.0518(3) 0.8453(2) 0.44237(18) 0.0231(4) Uani 1 1 d . . . H14A H 1.1711 0.8308 0.4263 0.028 Uiso 1 1 calc R . . C15 C 0.9581(2) 0.95215(19) 0.48829(16) 0.0180(4) Uani 1 1 d . . . C16 C 0.7800(3) 0.9652(2) 0.5125(2) 0.0270(5) Uani 1 1 d . . . H16A H 0.7108 1.0342 0.5449 0.032 Uiso 1 1 calc R . . C17 C 0.7069(3) 0.8768(2) 0.48888(19) 0.0254(5) Uani 1 1 d . . . H17A H 0.5877 0.8876 0.5066 0.030 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 0.01811(13) 0.01420(13) 0.02147(13) -0.00287(9) -0.00690(9) -0.00432(9) Cl1 0.0359(3) 0.0289(3) 0.0353(3) -0.0153(2) -0.0069(2) -0.0123(2) Cl2 0.0474(4) 0.0376(4) 0.0511(4) -0.0291(3) 0.0069(3) -0.0052(3) Cl3 0.0199(3) 0.0336(3) 0.0456(3) -0.0049(3) -0.0082(2) -0.0087(2) O1 0.0200(7) 0.0149(7) 0.0251(7) -0.0041(6) -0.0103(6) -0.0023(6) N1 0.0218(9) 0.0164(8) 0.0217(9) -0.0015(7) -0.0064(7) -0.0031(7) C1 0.0216(10) 0.0150(10) 0.0180(10) 0.0001(8) -0.0072(8) -0.0033(8) N2 0.0217(9) 0.0155(8) 0.0228(9) -0.0027(7) -0.0088(7) -0.0047(7) C2 0.0274(11) 0.0190(10) 0.0215(11) -0.0024(8) -0.0066(9) -0.0088(9) O2 0.0211(7) 0.0151(7) 0.0245(7) -0.0022(6) -0.0052(6) -0.0072(6) O3 0.0188(7) 0.0197(7) 0.0377(9) -0.0110(7) -0.0101(6) -0.0023(6) C3 0.0337(12) 0.0193(11) 0.0235(11) -0.0081(9) -0.0017(9) -0.0031(9) C4 0.0213(11) 0.0250(11) 0.0265(12) -0.0018(9) 0.0012(9) 0.0002(9) C5 0.0183(10) 0.0218(11) 0.0243(11) 0.0007(9) -0.0056(8) -0.0056(8) C6 0.0217(10) 0.0176(10) 0.0200(10) 0.0001(8) -0.0073(8) -0.0057(8) C7 0.0185(10) 0.0176(10) 0.0198(10) -0.0057(8) -0.0102(8) -0.0055(8) C8 0.0359(13) 0.0286(13) 0.0465(15) 0.0160(11) -0.0239(12) -0.0183(11) C9 0.0398(14) 0.0391(15) 0.0534(16) 0.0157(12) -0.0301(13) -0.0210(12) C10 0.0219(10) 0.0207(11) 0.0217(10) -0.0013(9) -0.0043(8) -0.0022(8) C11 0.0420(13) 0.0270(12) 0.0200(11) 0.0007(9) -0.0085(10) -0.0190(10) C12 0.0363(13) 0.0290(12) 0.0225(11) -0.0012(9) -0.0114(9) -0.0149(10) C13 0.0212(10) 0.0221(11) 0.0287(11) -0.0105(9) -0.0053(9) -0.0034(8) C14 0.0191(10) 0.0242(11) 0.0290(11) -0.0080(9) -0.0063(9) -0.0064(8) C15 0.0212(10) 0.0151(9) 0.0192(10) 0.0001(8) -0.0090(8) -0.0055(8) C16 0.0228(11) 0.0213(11) 0.0421(13) -0.0129(10) -0.0115(10) -0.0023(9) C17 0.0171(10) 0.0225(11) 0.0396(13) -0.0095(10) -0.0100(9) -0.0023(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 O3 1.9423(14) . ? Zn1 O2 2.0061(14) 2_666 ? Zn1 N1 2.1072(16) . ? Zn1 N2 2.1257(16) . ? Zn1 O1 2.1670(13) . ? Cl1 C2 1.737(2) . ? Cl2 C3 1.737(2) . ? Cl3 C5 1.730(2) . ? O1 C7 1.251(2) . ? N1 C8 1.324(3) . ? N1 C12 1.335(3) . ? C1 C2 1.386(3) . ? C1 C6 1.421(3) . ? C1 C7 1.499(3) . ? N2 C13 1.338(3) . ? N2 C17 1.346(3) . ? C2 C3 1.385(3) . ? O2 C7 1.266(2) . ? O2 Zn1 2.0061(14) 2_666 ? O3 C6 1.297(2) . ? C3 C4 1.382(3) . ? C4 C5 1.372(3) . ? C4 H4A 0.9300 . ? C5 C6 1.416(3) . ? C8 C9 1.379(3) . ? C8 H8A 0.9300 . ? C9 C10 1.387(3) . ? C9 H9A 0.9300 . ? C10 C11 1.389(3) . ? C10 C10 1.479(4) 2_675 ? C11 C12 1.382(3) . ? C11 H11A 0.9300 . ? C12 H12A 0.9300 . ? C13 C14 1.382(3) . ? C13 H13A 0.9300 . ? C14 C15 1.384(3) . ? C14 H14A 0.9300 . ? C15 C16 1.394(3) . ? C15 C15 1.489(4) 2_776 ? C16 C17 1.365(3) . ? C16 H16A 0.9300 . ? C17 H17A 0.9300 . ? 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 O3 Zn1 O2 144.41(6) . 2_666 ? O3 Zn1 N1 115.70(6) . . ? O2 Zn1 N1 99.55(6) 2_666 . ? O3 Zn1 N2 89.95(6) . . ? O2 Zn1 N2 90.62(6) 2_666 . ? N1 Zn1 N2 96.80(6) . . ? O3 Zn1 O1 88.67(5) . . ? O2 Zn1 O1 87.28(5) 2_666 . ? N1 Zn1 O1 88.78(6) . . ? N2 Zn1 O1 174.29(6) . . ? C7 O1 Zn1 114.05(12) . . ? C8 N1 C12 116.38(18) . . ? C8 N1 Zn1 120.44(14) . . ? C12 N1 Zn1 123.14(14) . . ? C2 C1 C6 120.96(18) . . ? C2 C1 C7 122.22(17) . . ? C6 C1 C7 116.75(17) . . ? C13 N2 C17 116.51(17) . . ? C13 N2 Zn1 123.25(14) . . ? C17 N2 Zn1 120.23(13) . . ? C3 C2 C1 120.86(18) . . ? C3 C2 Cl1 119.77(16) . . ? C1 C2 Cl1 119.29(16) . . ? C7 O2 Zn1 118.78(13) . 2_666 ? C6 O3 Zn1 128.42(13) . . ? C4 C3 C2 119.35(19) . . ? C4 C3 Cl2 119.53(17) . . ? C2 C3 Cl2 121.12(17) . . ? C5 C4 C3 120.32(19) . . ? C5 C4 H4A 119.8 . . ? C3 C4 H4A 119.8 . . ? C4 C5 C6 122.41(19) . . ? C4 C5 Cl3 119.71(16) . . ? C6 C5 Cl3 117.88(16) . . ? O3 C6 C5 120.68(18) . . ? O3 C6 C1 123.43(18) . . ? C5 C6 C1 115.83(18) . . ? O1 C7 O2 124.76(18) . . ? O1 C7 C1 118.90(17) . . ? O2 C7 C1 116.30(17) . . ? N1 C8 C9 123.5(2) . . ? N1 C8 H8A 118.2 . . ? C9 C8 H8A 118.2 . . ? C8 C9 C10 120.6(2) . . ? C8 C9 H9A 119.7 . . ? C10 C9 H9A 119.7 . . ? C9 C10 C11 115.73(19) . . ? C9 C10 C10 122.4(2) . 2_675 ? C11 C10 C10 121.9(2) . 2_675 ? C12 C11 C10 119.9(2) . . ? C12 C11 H11A 120.1 . . ? C10 C11 H11A 120.1 . . ? N1 C12 C11 123.8(2) . . ? N1 C12 H12A 118.1 . . ? C11 C12 H12A 118.1 . . ? N2 C13 C14 123.03(19) . . ? N2 C13 H13A 118.5 . . ? C14 C13 H13A 118.5 . . ? C13 C14 C15 120.31(19) . . ? C13 C14 H14A 119.8 . . ? C15 C14 H14A 119.8 . . ? C14 C15 C16 116.33(18) . . ? C14 C15 C15 122.2(2) . 2_776 ? C16 C15 C15 121.4(2) . 2_776 ? C17 C16 C15 120.1(2) . . ? C17 C16 H16A 119.9 . . ? C15 C16 H16A 119.9 . . ? N2 C17 C16 123.66(19) . . ? N2 C17 H17A 118.2 . . ? C16 C17 H17A 118.2 . . ? _diffrn_measured_fraction_theta_max 0.947 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.947 _refine_diff_density_max 0.439 _refine_diff_density_min -0.506 _refine_diff_density_rms 0.072 # Attachment '- Compound 9.cif' data_10ssg015_0m _database_code_depnum_ccdc_archive 'CCDC 774729' #TrackingRef '- Compound 9.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H16 Cl3 N3 O3 Zn' _chemical_formula_weight 578.13 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.1994(6) _cell_length_b 10.5683(7) _cell_length_c 13.8477(9) _cell_angle_alpha 80.486(2) _cell_angle_beta 78.545(2) _cell_angle_gamma 65.856(2) _cell_volume 1198.73(14) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 6119 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 30.39 _exptl_crystal_description Block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.602 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 1.393 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.790107 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS v.2.03 (Bruker, 2001), R(int)=0.0618 before correction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 APEX-2 CCD area detector' _diffrn_measurement_method '/w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_decay_% 0 _diffrn_reflns_number 15678 _diffrn_reflns_av_R_equivalents 0.0352 _diffrn_reflns_av_sigmaI/netI 0.0420 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.51 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5241 _reflns_number_gt 4471 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX-2' _computing_cell_refinement 'Bruker APEX-2' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0465P)^2^+1.0060P] 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 5241 _refine_ls_number_parameters 316 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0480 _refine_ls_R_factor_gt 0.0396 _refine_ls_wR_factor_ref 0.1004 _refine_ls_wR_factor_gt 0.0971 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _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 0.30518(3) 0.11286(3) 0.40453(2) 0.01553(10) Uani 1 1 d . . . Cl1 Cl 0.17113(9) -0.21066(8) 0.27711(6) 0.03310(18) Uani 1 1 d . . . Cl2 Cl 0.79827(10) -0.52350(9) 0.17401(7) 0.0433(2) Uani 1 1 d . . . Cl3 Cl 0.89180(8) -0.34795(7) 0.29757(5) 0.02451(16) Uani 1 1 d . . . O1 O 0.5720(2) -0.00287(18) 0.39947(13) 0.0190(4) Uani 1 1 d . . . N1 N 0.3435(3) 0.2336(2) 0.27451(16) 0.0198(5) Uani 1 1 d . . . C1 C 0.5714(3) -0.2042(3) 0.34478(19) 0.0176(5) Uani 1 1 d . . . N1A N 0.9269(4) -0.8055(3) 0.0450(2) 0.0460(7) Uani 1 1 d . . . C1A C 1.0216(5) -0.8229(4) -0.0401(3) 0.0544(10) Uani 1 1 d . . . H1AA H 0.9716 -0.7946 -0.0982 0.065 Uiso 1 1 calc R . . O2 O 0.6754(2) -0.20778(18) 0.48791(13) 0.0184(4) Uani 1 1 d . . . N2 N 0.0488(3) 0.2115(2) 0.43407(16) 0.0186(5) Uani 1 1 d . . . C2 C 0.6905(3) -0.3131(3) 0.2940(2) 0.0204(6) Uani 1 1 d . . . C2A C 1.1881(5) -0.8787(4) -0.0529(4) 0.0618(12) Uani 1 1 d . . . H2AA H 1.2480 -0.8835 -0.1175 0.074 Uiso 1 1 calc R . . O3 O 0.2916(2) -0.05601(18) 0.37692(14) 0.0201(4) Uani 1 1 d . . . C3 C 0.6514(3) -0.3884(3) 0.2383(2) 0.0268(6) Uani 1 1 d . . . C3A C 1.2660(6) -0.9273(5) 0.0292(4) 0.0667(13) Uani 1 1 d . . . C4 C 0.4901(4) -0.3566(3) 0.2344(2) 0.0295(7) Uani 1 1 d . . . H4A H 0.4614 -0.4106 0.1991 0.035 Uiso 1 1 calc R . . C4A C 1.1734(6) -0.9164(4) 0.1181(4) 0.0613(12) Uani 1 1 d . . . H4AA H 1.2209 -0.9482 0.1771 0.074 Uiso 1 1 calc R . . C5 C 0.3721(3) -0.2463(3) 0.2818(2) 0.0235(6) Uani 1 1 d . . . C5A C 1.0095(5) -0.8589(4) 0.1223(3) 0.0556(10) Uani 1 1 d . . . H5AA H 0.9478 -0.8564 0.1862 0.067 Uiso 1 1 calc R . . C6 C 0.4063(3) -0.1618(3) 0.33573(19) 0.0185(5) Uani 1 1 d . . . C6A C 1.4430(6) -0.9908(7) 0.0235(9) 0.155(4) Uani 1 1 d . . . H6AA H 1.4662 -1.0326 0.0879 0.186 Uiso 1 1 calc R . . C7 C 0.6101(3) -0.1317(3) 0.41449(18) 0.0154(5) Uani 1 1 d . . . C8 C 0.4950(3) 0.2122(3) 0.2289(2) 0.0279(7) Uani 1 1 d . . . H8A H 0.5823 0.1376 0.2552 0.033 Uiso 1 1 calc R . . C9 C 0.5284(3) 0.2934(3) 0.1462(2) 0.0287(7) Uani 1 1 d . . . H9A H 0.6368 0.2744 0.1167 0.034 Uiso 1 1 calc R . . C10 C 0.4027(3) 0.4039(3) 0.10559(19) 0.0198(5) Uani 1 1 d . . . C11 C 0.2462(3) 0.4228(3) 0.1509(2) 0.0244(6) Uani 1 1 d . . . H11A H 0.1564 0.4945 0.1249 0.029 Uiso 1 1 calc R . . C12 C 0.2225(3) 0.3363(3) 0.2341(2) 0.0238(6) Uani 1 1 d . . . H12A H 0.1152 0.3508 0.2638 0.029 Uiso 1 1 calc R . . C13 C 0.4284(3) 0.5010(3) 0.02156(19) 0.0206(5) Uani 1 1 d . . . H13A H 0.3361 0.5701 -0.0037 0.031 Uiso 1 1 calc R . . C14 C -0.4616(3) 0.4379(3) 0.4817(2) 0.0210(6) Uani 1 1 d . . . H14A H -0.5258 0.3961 0.4646 0.032 Uiso 1 1 calc R . . C15 C -0.2868(3) 0.3616(3) 0.46580(19) 0.0184(5) Uani 1 1 d . . . C16 C -0.1800(3) 0.4131(3) 0.4868(2) 0.0232(6) Uani 1 1 d . . . H16A H -0.2200 0.5013 0.5120 0.028 Uiso 1 1 calc R . . C17 C -0.0169(3) 0.3362(3) 0.4711(2) 0.0221(6) Uani 1 1 d . . . H17A H 0.0530 0.3730 0.4870 0.027 Uiso 1 1 calc R . . C18 C -0.0528(3) 0.1606(3) 0.4138(2) 0.0205(5) Uani 1 1 d . . . H18A H -0.0091 0.0724 0.3881 0.025 Uiso 1 1 calc R . . C19 C -0.2186(3) 0.2312(3) 0.4288(2) 0.0217(6) Uani 1 1 d . . . H19A H -0.2860 0.1910 0.4139 0.026 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 0.01144(17) 0.01548(15) 0.01763(16) 0.00030(11) -0.00173(11) -0.00407(11) Cl1 0.0189(4) 0.0406(4) 0.0439(4) -0.0114(3) -0.0092(3) -0.0109(3) Cl2 0.0265(4) 0.0477(5) 0.0517(5) -0.0345(4) -0.0045(4) 0.0000(4) Cl3 0.0126(3) 0.0286(3) 0.0284(4) -0.0082(3) -0.0006(3) -0.0030(3) O1 0.0176(10) 0.0153(9) 0.0225(9) -0.0010(7) -0.0016(8) -0.0056(7) N1 0.0161(12) 0.0212(11) 0.0205(11) 0.0026(9) -0.0025(9) -0.0074(9) C1 0.0159(13) 0.0159(12) 0.0190(12) 0.0000(10) -0.0036(10) -0.0043(10) N1A 0.0344(17) 0.059(2) 0.0413(17) -0.0085(15) 0.0030(14) -0.0172(15) C1A 0.052(3) 0.054(2) 0.049(2) -0.0012(18) -0.015(2) -0.010(2) O2 0.0137(9) 0.0173(9) 0.0211(9) -0.0016(7) -0.0053(7) -0.0020(7) N2 0.0125(11) 0.0184(10) 0.0220(11) 0.0002(8) -0.0019(9) -0.0042(9) C2 0.0123(13) 0.0235(13) 0.0226(13) -0.0030(10) -0.0032(11) -0.0035(10) C2A 0.045(3) 0.050(2) 0.076(3) -0.006(2) 0.005(2) -0.011(2) O3 0.0118(9) 0.0176(9) 0.0286(10) -0.0048(7) -0.0016(8) -0.0032(7) C3 0.0204(15) 0.0266(14) 0.0291(15) -0.0140(12) -0.0001(12) -0.0024(12) C3A 0.049(3) 0.046(2) 0.107(4) -0.016(2) -0.004(3) -0.021(2) C4 0.0246(16) 0.0316(15) 0.0340(16) -0.0127(13) -0.0072(13) -0.0079(13) C4A 0.058(3) 0.049(2) 0.077(3) -0.008(2) -0.029(3) -0.011(2) C5 0.0170(14) 0.0277(14) 0.0275(14) -0.0020(11) -0.0072(11) -0.0086(11) C5A 0.051(3) 0.051(2) 0.059(3) -0.0052(19) -0.009(2) -0.013(2) C6 0.0162(13) 0.0181(12) 0.0199(13) 0.0004(10) -0.0029(10) -0.0061(10) C6A 0.040(3) 0.073(4) 0.360(14) -0.092(6) 0.006(6) -0.018(3) C7 0.0080(12) 0.0191(12) 0.0164(12) -0.0023(9) 0.0013(9) -0.0036(9) C8 0.0159(14) 0.0312(15) 0.0287(15) 0.0101(12) -0.0030(12) -0.0063(12) C9 0.0129(14) 0.0361(16) 0.0285(15) 0.0097(12) 0.0001(12) -0.0071(12) C10 0.0204(14) 0.0213(13) 0.0173(12) -0.0002(10) -0.0008(11) -0.0090(11) C11 0.0177(14) 0.0253(14) 0.0241(14) 0.0046(11) -0.0035(11) -0.0045(11) C12 0.0163(14) 0.0260(14) 0.0248(14) 0.0044(11) -0.0021(11) -0.0068(11) C13 0.0206(14) 0.0230(13) 0.0168(13) 0.0027(10) -0.0042(10) -0.0082(11) C14 0.0125(13) 0.0233(13) 0.0266(14) 0.0002(11) -0.0019(11) -0.0077(11) C15 0.0119(13) 0.0199(12) 0.0203(13) 0.0019(10) -0.0010(10) -0.0050(10) C16 0.0158(14) 0.0189(13) 0.0331(15) -0.0057(11) -0.0004(12) -0.0050(11) C17 0.0146(14) 0.0207(13) 0.0314(15) -0.0037(11) -0.0025(11) -0.0072(11) C18 0.0167(14) 0.0205(13) 0.0227(13) -0.0043(10) -0.0010(11) -0.0056(11) C19 0.0156(14) 0.0230(13) 0.0266(14) -0.0030(11) -0.0029(11) -0.0074(11) _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 O3 1.9425(18) . ? Zn1 O2 2.0007(18) 2_656 ? Zn1 N1 2.086(2) . ? Zn1 N2 2.136(2) . ? Zn1 O1 2.2427(18) . ? Cl1 C5 1.742(3) . ? Cl2 C3 1.738(3) . ? Cl3 C2 1.744(3) . ? O1 C7 1.251(3) . ? N1 C12 1.337(3) . ? N1 C8 1.353(4) . ? C1 C2 1.396(4) . ? C1 C6 1.422(4) . ? C1 C7 1.500(4) . ? N1A C1A 1.310(5) . ? N1A C5A 1.346(5) . ? C1A C2A 1.383(6) . ? C1A H1AA 0.9500 . ? O2 C7 1.272(3) . ? O2 Zn1 2.0007(18) 2_656 ? N2 C18 1.345(3) . ? N2 C17 1.347(3) . ? C2 C3 1.380(4) . ? C2A C3A 1.378(7) . ? C2A H2AA 0.9500 . ? O3 C6 1.302(3) . ? C3 C4 1.391(4) . ? C3A C4A 1.343(7) . ? C3A C6A 1.477(7) . ? C4 C5 1.380(4) . ? C4 H4A 0.9500 . ? C4A C5A 1.368(6) . ? C4A H4AA 0.9500 . ? C5 C6 1.413(4) . ? C5A H5AA 0.9500 . ? C6A C6A 1.079(14) 2_835 ? C6A H6AA 0.9500 . ? C8 C9 1.376(4) . ? C8 H8A 0.9500 . ? C9 C10 1.398(4) . ? C9 H9A 0.9500 . ? C10 C11 1.398(4) . ? C10 C13 1.469(4) . ? C11 C12 1.387(4) . ? C11 H11A 0.9500 . ? C12 H12A 0.9500 . ? C13 C13 1.328(5) 2_665 ? C13 H13A 0.9500 . ? C14 C14 1.342(5) 2_466 ? C14 C15 1.464(4) . ? C14 H14A 0.9500 . ? C15 C16 1.396(4) . ? C15 C19 1.398(4) . ? C16 C17 1.375(4) . ? C16 H16A 0.9500 . ? C17 H17A 0.9500 . ? C18 C19 1.386(4) . ? C18 H18A 0.9500 . ? C19 H19A 0.9500 . ? 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 O3 Zn1 O2 143.32(8) . 2_656 ? O3 Zn1 N1 111.54(8) . . ? O2 Zn1 N1 104.49(8) 2_656 . ? O3 Zn1 N2 90.99(8) . . ? O2 Zn1 N2 90.23(8) 2_656 . ? N1 Zn1 N2 98.65(8) . . ? O3 Zn1 O1 88.85(7) . . ? O2 Zn1 O1 84.43(7) 2_656 . ? N1 Zn1 O1 89.97(8) . . ? N2 Zn1 O1 170.78(7) . . ? C7 O1 Zn1 111.73(16) . . ? C12 N1 C8 117.3(2) . . ? C12 N1 Zn1 122.37(18) . . ? C8 N1 Zn1 120.33(17) . . ? C2 C1 C6 120.9(2) . . ? C2 C1 C7 121.9(2) . . ? C6 C1 C7 117.1(2) . . ? C1A N1A C5A 112.3(3) . . ? N1A C1A C2A 125.7(4) . . ? N1A C1A H1AA 117.1 . . ? C2A C1A H1AA 117.1 . . ? C7 O2 Zn1 117.82(16) . 2_656 ? C18 N2 C17 117.2(2) . . ? C18 N2 Zn1 124.35(18) . . ? C17 N2 Zn1 118.37(18) . . ? C3 C2 C1 121.2(2) . . ? C3 C2 Cl3 120.1(2) . . ? C1 C2 Cl3 118.7(2) . . ? C3A C2A C1A 119.2(4) . . ? C3A C2A H2AA 120.4 . . ? C1A C2A H2AA 120.4 . . ? C6 O3 Zn1 127.55(17) . . ? C2 C3 C4 119.2(3) . . ? C2 C3 Cl2 121.8(2) . . ? C4 C3 Cl2 119.0(2) . . ? C4A C3A C2A 117.0(4) . . ? C4A C3A C6A 119.5(6) . . ? C2A C3A C6A 123.4(6) . . ? C5 C4 C3 119.8(3) . . ? C5 C4 H4A 120.1 . . ? C3 C4 H4A 120.1 . . ? C3A C4A C5A 119.0(4) . . ? C3A C4A H4AA 120.5 . . ? C5A C4A H4AA 120.5 . . ? C4 C5 C6 123.0(3) . . ? C4 C5 Cl1 118.7(2) . . ? C6 C5 Cl1 118.2(2) . . ? N1A C5A C4A 126.6(4) . . ? N1A C5A H5AA 116.7 . . ? C4A C5A H5AA 116.7 . . ? O3 C6 C5 121.1(2) . . ? O3 C6 C1 123.3(2) . . ? C5 C6 C1 115.5(2) . . ? C6A C6A C3A 145.8(17) 2_835 . ? C6A C6A H6AA 107.1 2_835 . ? C3A C6A H6AA 107.1 . . ? O1 C7 O2 124.7(2) . . ? O1 C7 C1 119.2(2) . . ? O2 C7 C1 116.1(2) . . ? N1 C8 C9 123.1(2) . . ? N1 C8 H8A 118.5 . . ? C9 C8 H8A 118.5 . . ? C8 C9 C10 119.9(3) . . ? C8 C9 H9A 120.1 . . ? C10 C9 H9A 120.1 . . ? C11 C10 C9 116.9(2) . . ? C11 C10 C13 119.8(2) . . ? C9 C10 C13 123.3(2) . . ? C12 C11 C10 119.7(2) . . ? C12 C11 H11A 120.1 . . ? C10 C11 H11A 120.1 . . ? N1 C12 C11 123.1(3) . . ? N1 C12 H12A 118.4 . . ? C11 C12 H12A 118.4 . . ? C13 C13 C10 124.5(3) 2_665 . ? C13 C13 H13A 117.7 2_665 . ? C10 C13 H13A 117.7 . . ? C14 C14 C15 125.2(3) 2_466 . ? C14 C14 H14A 117.4 2_466 . ? C15 C14 H14A 117.4 . . ? C16 C15 C19 116.6(2) . . ? C16 C15 C14 122.7(2) . . ? C19 C15 C14 120.7(2) . . ? C17 C16 C15 120.1(3) . . ? C17 C16 H16A 119.9 . . ? C15 C16 H16A 119.9 . . ? N2 C17 C16 123.3(3) . . ? N2 C17 H17A 118.4 . . ? C16 C17 H17A 118.4 . . ? N2 C18 C19 122.8(2) . . ? N2 C18 H18A 118.6 . . ? C19 C18 H18A 118.6 . . ? C18 C19 C15 120.0(3) . . ? C18 C19 H19A 120.0 . . ? C15 C19 H19A 120.0 . . ? _diffrn_measured_fraction_theta_max 0.954 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.954 _refine_diff_density_max 1.062 _refine_diff_density_min -1.233 _refine_diff_density_rms 0.086 # Attachment '- Compound 10.cif' data_10ssg023_0m _database_code_depnum_ccdc_archive 'CCDC 817005' #TrackingRef '- Compound 10.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H16 Cl3 Co N3 O3' _chemical_formula_weight 571.69 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' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.1940(4) _cell_length_b 10.5320(5) _cell_length_c 13.8552(6) _cell_angle_alpha 80.603(2) _cell_angle_beta 78.290(2) _cell_angle_gamma 65.9750(10) _cell_volume 1195.00(9) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 7033 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 31.27 _exptl_crystal_description Cube _exptl_crystal_colour Purple _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.589 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 578 _exptl_absorpt_coefficient_mu 1.087 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.872641 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS v.2.03 (Bruker, 2001), R(int)=0.0448 before correction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 APEX-2 CCD area detector' _diffrn_measurement_method '/w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_decay_% 0 _diffrn_reflns_number 20799 _diffrn_reflns_av_R_equivalents 0.0344 _diffrn_reflns_av_sigmaI/netI 0.0423 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.51 _diffrn_reflns_theta_max 30.00 _reflns_number_total 6677 _reflns_number_gt 5442 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX-2' _computing_cell_refinement 'Bruker APEX-2' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0396P)^2^+2.3996P] 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 6677 _refine_ls_number_parameters 379 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0578 _refine_ls_R_factor_gt 0.0459 _refine_ls_wR_factor_ref 0.1157 _refine_ls_wR_factor_gt 0.1113 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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 Co1 Co 0.19657(4) 0.38783(3) 0.09552(2) 0.01528(9) Uani 1 1 d . . . N1 N 0.1563(3) 0.2683(2) 0.22567(16) 0.0199(4) Uani 1 1 d . . . N1A N -0.5708(9) 0.6849(15) 0.5460(11) 0.033(3) Uani 0.67 1 d P A 1 C1' C -0.303(3) 0.592(3) 0.5922(15) 0.042(5) Uani 0.33 1 d P B 2 H1'A H -0.2424 0.5676 0.6435 0.050 Uiso 0.33 1 calc PR B 2 N1A' N -0.569(3) 0.702(4) 0.546(2) 0.054(8) Uani 0.33 1 d P B 2 O1 O -0.1771(2) 0.70385(19) 0.01443(13) 0.0202(4) Uani 1 1 d . . . Cl2 Cl -0.39135(7) 0.84881(7) 0.20223(5) 0.02385(14) Uani 1 1 d . . . O2 O 0.2094(2) 0.55647(19) 0.12441(14) 0.0199(4) Uani 1 1 d . . . N2 N 0.4510(2) 0.2896(2) 0.06627(16) 0.0182(4) Uani 1 1 d . . . C2A C -0.0579(6) 0.5046(6) 0.5394(4) 0.0390(11) Uani 0.67 1 d P . 1 H2AA H -0.0255 0.4665 0.6007 0.059 Uiso 0.67 1 calc PR . 1 C2' C -0.0553(11) 0.5298(10) 0.4694(7) 0.0284(19) Uani 0.33 1 d P . 2 H2'A H -0.0157 0.5401 0.4025 0.043 Uiso 0.33 1 calc PR . 2 Cl3 Cl 0.32804(8) 0.71396(8) 0.22295(6) 0.03092(17) Uani 1 1 d . . . O3 O -0.0655(2) 0.49987(18) 0.10169(13) 0.0189(4) Uani 1 1 d . . . C3A C -0.3028(17) 0.6212(18) 0.4515(9) 0.041(3) Uani 0.67 1 d P A 1 H3AA H -0.2377 0.6184 0.3904 0.049 Uiso 0.67 1 calc PR A 1 C3' C -0.233(2) 0.5811(18) 0.4959(13) 0.033(4) Uani 0.33 1 d P B 2 Cl4 Cl -0.29973(9) 1.02658(9) 0.32466(7) 0.0411(2) Uani 1 1 d . . . C4 C -0.1524(3) 0.8915(3) 0.2612(2) 0.0264(6) Uani 1 1 d . . . C4A C -0.2305(9) 0.5701(8) 0.5354(7) 0.0292(14) Uani 0.67 1 d P A 1 C4' C -0.327(4) 0.622(3) 0.4269(16) 0.032(4) Uani 0.33 1 d P B 2 H4'A H -0.2928 0.6173 0.3592 0.038 Uiso 0.33 1 calc PR B 2 C5 C 0.0093(3) 0.8598(3) 0.2650(2) 0.0273(6) Uani 1 1 d . . . H5A H 0.0371 0.9136 0.2993 0.033 Uiso 1 1 calc R . . C5A C -0.3331(12) 0.5790(10) 0.6246(7) 0.0300(16) Uani 0.67 1 d P A 1 H5AA H -0.2902 0.5444 0.6833 0.036 Uiso 0.67 1 calc PR A 1 C5' C -0.470(5) 0.667(4) 0.468(3) 0.076(12) Uani 0.33 1 d P B 2 H5'A H -0.5320 0.6829 0.4185 0.092 Uiso 0.33 1 calc PR B 2 C6 C -0.0291(3) 0.2082(3) 0.3554(2) 0.0277(6) Uani 1 1 d . . . H6A H -0.1352 0.2272 0.3848 0.033 Uiso 1 1 calc R . . C6A C -0.4942(15) 0.6372(17) 0.6275(11) 0.033(2) Uani 0.67 1 d P A 1 H6AA H -0.5580 0.6455 0.6894 0.039 Uiso 0.67 1 calc PR A 1 C6' C -0.481(5) 0.645(4) 0.610(3) 0.067(11) Uani 0.33 1 d P B 2 H6'A H -0.5301 0.6356 0.6753 0.080 Uiso 0.33 1 calc PR B 2 C7 C 0.0055(3) 0.2883(3) 0.2723(2) 0.0267(6) Uani 1 1 d . . . H7A H -0.0802 0.3607 0.2466 0.032 Uiso 1 1 calc R . . C7A C -0.4801(12) 0.6805(16) 0.4549(11) 0.035(2) Uani 0.67 1 d P A 1 H7AA H -0.5270 0.7130 0.3975 0.042 Uiso 0.67 1 calc PR A 1 C8 C 0.2539(3) 0.0788(3) 0.3488(2) 0.0249(6) Uani 1 1 d . . . H8A H 0.3420 0.0079 0.3734 0.030 Uiso 1 1 calc R . . C9 C 0.2772(3) 0.1655(3) 0.2664(2) 0.0230(5) Uani 1 1 d . . . H9A H 0.3824 0.1521 0.2375 0.028 Uiso 1 1 calc R . . C10 C 0.5523(3) 0.3404(3) 0.0869(2) 0.0200(5) Uani 1 1 d . . . H10A H 0.5096 0.4266 0.1126 0.024 Uiso 1 1 calc R . . C11 C -0.0706(3) 0.7050(3) 0.15495(18) 0.0169(5) Uani 1 1 d . . . C12 C 0.6803(3) 0.0869(3) 0.0130(2) 0.0232(5) Uani 1 1 d . . . H12A H 0.7196 0.0004 -0.0121 0.028 Uiso 1 1 calc R . . C13 C 0.0724(3) -0.0004(3) 0.47889(19) 0.0211(5) Uani 1 1 d . . . H13A H 0.1625 -0.0671 0.5040 0.032 Uiso 1 1 calc R . . C14 C 0.9619(3) 0.0620(3) 0.0187(2) 0.0201(5) Uani 1 1 d . . . H14A H 1.0248 0.1025 0.0360 0.030 Uiso 1 1 calc R . . C15 C -0.1911(3) 0.8145(3) 0.20569(19) 0.0191(5) Uani 1 1 d . . . C16 C 0.0944(3) 0.6634(3) 0.16458(18) 0.0172(5) Uani 1 1 d . . . C17 C 0.5165(3) 0.1644(3) 0.0290(2) 0.0228(5) Uani 1 1 d . . . H17A H 0.4480 0.1284 0.0134 0.027 Uiso 1 1 calc R . . C18 C 0.7190(3) 0.2692(3) 0.0713(2) 0.0208(5) Uani 1 1 d . . . H18A H 0.7850 0.3090 0.0854 0.025 Uiso 1 1 calc R . . C19 C 0.0974(3) 0.0977(3) 0.39531(19) 0.0195(5) Uani 1 1 d . . . C20 C -0.1085(3) 0.6296(3) 0.08666(18) 0.0155(4) Uani 1 1 d . . . C21 C 0.7873(3) 0.1384(3) 0.03458(19) 0.0184(5) Uani 1 1 d . . . C22 C 0.1277(3) 0.7490(3) 0.2182(2) 0.0224(5) 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 Co1 0.01227(15) 0.01511(16) 0.01721(16) -0.00012(12) -0.00232(12) -0.00449(12) N1 0.0172(10) 0.0221(11) 0.0192(10) 0.0030(8) -0.0030(8) -0.0080(9) N1A 0.012(3) 0.034(4) 0.047(6) -0.007(3) -0.006(3) -0.001(2) C1' 0.043(11) 0.056(10) 0.030(12) 0.009(9) -0.012(9) -0.024(8) N1A' 0.088(16) 0.052(12) 0.028(11) -0.002(8) 0.008(9) -0.041(10) O1 0.0169(8) 0.0192(9) 0.0215(9) -0.0028(7) -0.0074(7) -0.0016(7) Cl2 0.0127(3) 0.0277(3) 0.0279(3) -0.0073(3) -0.0013(2) -0.0037(2) O2 0.0126(8) 0.0180(9) 0.0285(10) -0.0037(7) -0.0037(7) -0.0045(7) N2 0.0118(9) 0.0188(10) 0.0207(10) 0.0002(8) -0.0005(8) -0.0042(8) C2A 0.029(3) 0.042(3) 0.042(4) -0.003(2) -0.005(2) -0.010(2) C2' 0.023(5) 0.034(5) 0.020(5) -0.007(4) 0.003(4) -0.004(4) Cl3 0.0193(3) 0.0364(4) 0.0418(4) -0.0076(3) -0.0106(3) -0.0112(3) O3 0.0157(8) 0.0165(8) 0.0227(9) -0.0020(7) -0.0019(7) -0.0049(7) C3A 0.035(5) 0.056(4) 0.033(7) -0.007(5) -0.006(5) -0.017(4) C3' 0.032(6) 0.044(7) 0.019(7) -0.012(6) -0.015(7) -0.001(5) Cl4 0.0264(4) 0.0434(5) 0.0501(5) -0.0312(4) -0.0051(3) -0.0004(3) C4 0.0215(13) 0.0301(15) 0.0271(14) -0.0108(11) -0.0027(11) -0.0068(11) C4A 0.025(3) 0.031(3) 0.033(4) -0.002(4) -0.006(4) -0.011(2) C4' 0.035(11) 0.042(7) 0.019(9) -0.008(7) -0.001(7) -0.015(7) C5 0.0254(14) 0.0301(15) 0.0300(15) -0.0106(12) -0.0083(11) -0.0096(12) C5A 0.032(4) 0.029(3) 0.031(5) 0.002(3) -0.011(3) -0.013(3) C5' 0.13(3) 0.048(13) 0.062(18) 0.019(11) -0.059(17) -0.032(15) C6 0.0162(12) 0.0314(15) 0.0290(14) 0.0067(12) -0.0010(10) -0.0073(11) C6A 0.033(4) 0.038(4) 0.027(5) 0.004(3) -0.007(4) -0.015(3) C6' 0.09(2) 0.040(12) 0.037(13) -0.006(9) 0.024(10) -0.005(11) C7 0.0150(12) 0.0270(14) 0.0298(14) 0.0089(11) -0.0036(10) -0.0040(11) C7A 0.026(3) 0.039(5) 0.024(4) 0.005(3) -0.004(3) 0.000(3) C8 0.0174(12) 0.0232(13) 0.0280(14) 0.0079(11) -0.0061(10) -0.0044(10) C9 0.0170(12) 0.0261(13) 0.0224(13) 0.0032(11) -0.0019(10) -0.0072(11) C10 0.0156(11) 0.0186(12) 0.0244(13) -0.0027(10) -0.0013(9) -0.0058(10) C11 0.0146(11) 0.0163(11) 0.0190(11) -0.0005(9) -0.0032(9) -0.0052(9) C12 0.0146(11) 0.0212(13) 0.0316(14) -0.0075(11) -0.0011(10) -0.0042(10) C13 0.0199(12) 0.0228(13) 0.0192(12) 0.0008(10) -0.0041(10) -0.0072(11) C14 0.0128(11) 0.0190(12) 0.0283(13) -0.0009(10) -0.0030(9) -0.0063(9) C15 0.0122(10) 0.0210(12) 0.0225(12) -0.0037(10) -0.0035(9) -0.0039(9) C16 0.0145(11) 0.0164(11) 0.0186(11) 0.0013(9) -0.0019(9) -0.0053(9) C17 0.0151(11) 0.0222(13) 0.0311(14) -0.0027(11) -0.0034(10) -0.0073(10) C18 0.0151(11) 0.0214(12) 0.0264(13) -0.0029(10) -0.0039(10) -0.0069(10) C19 0.0183(11) 0.0224(12) 0.0181(12) -0.0002(10) -0.0029(9) -0.0087(10) C20 0.0097(10) 0.0183(11) 0.0169(11) -0.0020(9) 0.0008(8) -0.0049(9) C21 0.0132(11) 0.0205(12) 0.0199(12) 0.0009(9) -0.0011(9) -0.0067(9) C22 0.0160(11) 0.0269(13) 0.0263(13) -0.0009(11) -0.0072(10) -0.0091(10) _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 Co1 O2 1.9369(19) . ? Co1 O1 2.0040(18) 2_565 ? Co1 N1 2.084(2) . ? Co1 N2 2.118(2) . ? Co1 O3 2.2000(17) . ? N1 C9 1.342(3) . ? N1 C7 1.352(3) . ? N1A C7A 1.36(2) . ? N1A C6A 1.368(16) . ? C1' C3' 1.36(2) . ? C1' C6' 1.48(4) . ? C1' H1'A 0.9300 . ? N1A' C6' 1.23(4) . ? N1A' C5' 1.26(6) . ? O1 C20 1.269(3) . ? O1 Co1 2.0040(18) 2_565 ? Cl2 C15 1.735(2) . ? O2 C16 1.301(3) . ? N2 C10 1.341(3) . ? N2 C17 1.348(4) . ? C2A C2A 1.347(11) 2_566 ? C2A C4A 1.459(10) . ? C2A H2AA 0.9300 . ? C2' C2' 1.343(18) 2_566 ? C2' C3' 1.48(2) . ? C2' H2'A 0.9300 . ? Cl3 C22 1.738(3) . ? O3 C20 1.252(3) . ? C3A C4A 1.379(11) . ? C3A C7A 1.483(17) . ? C3A H3AA 0.9300 . ? C3' C4' 1.322(19) . ? Cl4 C4 1.729(3) . ? C4 C15 1.387(4) . ? C4 C5 1.396(4) . ? C4A C5A 1.385(9) . ? C4' C5' 1.24(5) . ? C4' H4'A 0.9300 . ? C5 C22 1.376(4) . ? C5 H5A 0.9300 . ? C5A C6A 1.348(16) . ? C5A H5AA 0.9300 . ? C5' C6' 1.94(6) . ? C5' H5'A 0.9300 . ? C6 C7 1.375(4) . ? C6 C19 1.400(4) . ? C6 H6A 0.9300 . ? C6A H6AA 0.9300 . ? C6' H6'A 0.9300 . ? C7 H7A 0.9300 . ? C7A H7AA 0.9300 . ? C8 C9 1.380(4) . ? C8 C19 1.399(4) . ? C8 H8A 0.9300 . ? C9 H9A 0.9300 . ? C10 C18 1.392(3) . ? C10 H10A 0.9300 . ? C11 C15 1.400(4) . ? C11 C16 1.426(3) . ? C11 C20 1.500(3) . ? C12 C17 1.381(4) . ? C12 C21 1.400(4) . ? C12 H12A 0.9300 . ? C13 C13 1.338(5) 2_556 ? C13 C19 1.468(4) . ? C13 H13A 0.9300 . ? C14 C14 1.339(5) 2_755 ? C14 C21 1.461(3) . ? C14 H14A 0.9300 . ? C16 C22 1.412(4) . ? C17 H17A 0.9300 . ? C18 C21 1.395(4) . ? C18 H18A 0.9300 . ? 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 O2 Co1 O1 142.46(8) . 2_565 ? O2 Co1 N1 110.79(9) . . ? O1 Co1 N1 105.99(9) 2_565 . ? O2 Co1 N2 91.19(8) . . ? O1 Co1 N2 90.46(8) 2_565 . ? N1 Co1 N2 98.76(8) . . ? O2 Co1 O3 89.09(7) . . ? O1 Co1 O3 84.05(7) 2_565 . ? N1 Co1 O3 89.26(8) . . ? N2 Co1 O3 171.29(8) . . ? C9 N1 C7 116.4(2) . . ? C9 N1 Co1 122.24(18) . . ? C7 N1 Co1 121.35(17) . . ? C7A N1A C6A 118.7(10) . . ? C3' C1' C6' 116(2) . . ? C3' C1' H1'A 122.0 . . ? C6' C1' H1'A 122.0 . . ? C6' N1A' C5' 102(3) . . ? C20 O1 Co1 119.92(16) . 2_565 ? C16 O2 Co1 127.94(16) . . ? C10 N2 C17 117.3(2) . . ? C10 N2 Co1 124.35(18) . . ? C17 N2 Co1 118.27(17) . . ? C2A C2A C4A 124.6(8) 2_566 . ? C2A C2A H2AA 117.7 2_566 . ? C4A C2A H2AA 117.7 . . ? C2' C2' C3' 127.6(13) 2_566 . ? C2' C2' H2'A 116.2 2_566 . ? C3' C2' H2'A 116.2 . . ? C20 O3 Co1 113.31(15) . . ? C4A C3A C7A 122.7(13) . . ? C4A C3A H3AA 118.7 . . ? C7A C3A H3AA 118.7 . . ? C4' C3' C1' 119(2) . . ? C4' C3' C2' 121(2) . . ? C1' C3' C2' 120.3(15) . . ? C15 C4 C5 119.2(3) . . ? C15 C4 Cl4 121.5(2) . . ? C5 C4 Cl4 119.3(2) . . ? C3A C4A C5A 116.2(10) . . ? C3A C4A C2A 126.7(9) . . ? C5A C4A C2A 117.1(9) . . ? C5' C4' C3' 108(3) . . ? C5' C4' H4'A 125.8 . . ? C3' C4' H4'A 125.8 . . ? C22 C5 C4 119.9(3) . . ? C22 C5 H5A 120.0 . . ? C4 C5 H5A 120.0 . . ? C6A C5A C4A 120.9(10) . . ? C6A C5A H5AA 119.6 . . ? C4A C5A H5AA 119.6 . . ? C4' C5' N1A' 148(4) . . ? C4' C5' C6' 110(3) . . ? N1A' C5' C6' 39(2) . . ? C4' C5' H5'A 105.9 . . ? N1A' C5' H5'A 105.9 . . ? C6' C5' H5'A 142.1 . . ? C7 C6 C19 119.2(2) . . ? C7 C6 H6A 120.4 . . ? C19 C6 H6A 120.4 . . ? C5A C6A N1A 124.7(13) . . ? C5A C6A H6AA 117.6 . . ? N1A C6A H6AA 117.6 . . ? N1A' C6' C1' 125(3) . . ? N1A' C6' C5' 40(2) . . ? C1' C6' C5' 87(2) . . ? N1A' C6' H6'A 117.5 . . ? C1' C6' H6'A 117.5 . . ? C5' C6' H6'A 154.1 . . ? N1 C7 C6 124.1(2) . . ? N1 C7 H7A 118.0 . . ? C6 C7 H7A 118.0 . . ? N1A C7A C3A 116.7(12) . . ? N1A C7A H7AA 121.6 . . ? C3A C7A H7AA 121.6 . . ? C9 C8 C19 119.8(2) . . ? C9 C8 H8A 120.1 . . ? C19 C8 H8A 120.1 . . ? N1 C9 C8 123.5(2) . . ? N1 C9 H9A 118.2 . . ? C8 C9 H9A 118.2 . . ? N2 C10 C18 122.7(2) . . ? N2 C10 H10A 118.7 . . ? C18 C10 H10A 118.7 . . ? C15 C11 C16 120.8(2) . . ? C15 C11 C20 121.8(2) . . ? C16 C11 C20 117.4(2) . . ? C17 C12 C21 120.0(3) . . ? C17 C12 H12A 120.0 . . ? C21 C12 H12A 120.0 . . ? C13 C13 C19 124.0(3) 2_556 . ? C13 C13 H13A 118.0 2_556 . ? C19 C13 H13A 118.0 . . ? C14 C14 C21 125.0(3) 2_755 . ? C14 C14 H14A 117.5 2_755 . ? C21 C14 H14A 117.5 . . ? C4 C15 C11 120.9(2) . . ? C4 C15 Cl2 120.1(2) . . ? C11 C15 Cl2 118.97(19) . . ? O2 C16 C22 121.1(2) . . ? O2 C16 C11 123.1(2) . . ? C22 C16 C11 115.7(2) . . ? N2 C17 C12 123.3(2) . . ? N2 C17 H17A 118.4 . . ? C12 C17 H17A 118.4 . . ? C10 C18 C21 120.3(2) . . ? C10 C18 H18A 119.9 . . ? C21 C18 H18A 119.9 . . ? C8 C19 C6 116.9(2) . . ? C8 C19 C13 119.7(2) . . ? C6 C19 C13 123.3(2) . . ? O3 C20 O1 124.8(2) . . ? O3 C20 C11 119.0(2) . . ? O1 C20 C11 116.2(2) . . ? C18 C21 C12 116.5(2) . . ? C18 C21 C14 120.9(2) . . ? C12 C21 C14 122.6(2) . . ? C5 C22 C16 123.1(2) . . ? C5 C22 Cl3 118.8(2) . . ? C16 C22 Cl3 118.1(2) . . ? _diffrn_measured_fraction_theta_max 0.961 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.961 _refine_diff_density_max 0.753 _refine_diff_density_min -0.503 _refine_diff_density_rms 0.090 # Attachment '- Compound 11.cif' data_10sd003_0m _database_code_depnum_ccdc_archive 'CCDC 817006' #TrackingRef '- Compound 11.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H17 Cl3 N4 Ni O6' _chemical_formula_weight 634.49 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' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.8694(3) _cell_length_b 10.1833(3) _cell_length_c 13.5295(4) _cell_angle_alpha 92.1540(10) _cell_angle_beta 103.1460(10) _cell_angle_gamma 104.0380(10) _cell_volume 1278.37(7) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3503 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 26.12 _exptl_crystal_description Cube _exptl_crystal_colour green _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.648 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 644 _exptl_absorpt_coefficient_mu 1.123 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.876687 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ; SADABS v.2.03 (Bruker, 2001), R(int)=0.0478 before correction ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 APEX-2 CCD area detector' _diffrn_measurement_method '/w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_decay_% 0 _diffrn_reflns_number 18784 _diffrn_reflns_av_R_equivalents 0.0488 _diffrn_reflns_av_sigmaI/netI 0.0463 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 25.78 _reflns_number_total 4868 _reflns_number_gt 3836 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX-2' _computing_cell_refinement 'Bruker APEX-2' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0345P)^2^+0.5104P] 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 4868 _refine_ls_number_parameters 352 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0526 _refine_ls_R_factor_gt 0.0363 _refine_ls_wR_factor_ref 0.0826 _refine_ls_wR_factor_gt 0.0764 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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 Ni1 Ni 0.30678(3) 0.15180(3) 0.32435(2) 0.01680(10) Uani 1 1 d . . . Cl1 Cl -0.35096(9) 0.48824(9) 0.10625(7) 0.0489(2) Uani 1 1 d . . . O1S O 0.35648(18) -0.03669(18) 0.35100(14) 0.0240(4) Uani 1 1 d . . . O1 O 0.21853(18) 0.30855(18) 0.28783(14) 0.0227(4) Uani 1 1 d . . . N1 N 0.5141(2) 0.2714(2) 0.36946(16) 0.0204(5) Uani 1 1 d . . . N1S N 0.2238(2) -0.1028(2) 0.32617(16) 0.0230(5) Uani 1 1 d . . . C1 C 0.0341(3) 0.4048(3) 0.1968(2) 0.0226(6) Uani 1 1 d . . . Cl2 Cl 0.17291(9) 0.75535(8) 0.07559(6) 0.0412(2) Uani 1 1 d . . . N2 N 0.2850(2) 0.1615(2) 0.47472(16) 0.0193(5) Uani 1 1 d . . . O2S O 0.13476(18) -0.03295(18) 0.29422(14) 0.0228(4) Uani 1 1 d . . . O2 O -0.0089(2) 0.1902(2) 0.26188(16) 0.0359(5) Uani 1 1 d . . . C2 C 0.1237(3) 0.5159(3) 0.1643(2) 0.0255(6) Uani 1 1 d . . . Cl3 Cl 0.30541(8) 0.53196(8) 0.17631(6) 0.0401(2) Uani 1 1 d . . . O3S O 0.1861(2) -0.22424(19) 0.33404(15) 0.0364(5) Uani 1 1 d . . . O3 O -0.20923(19) 0.2883(2) 0.19677(15) 0.0324(5) Uani 1 1 d . . . H3A H -0.1662 0.2335 0.2222 0.049 Uiso 1 1 calc R . . C3 C 0.0664(3) 0.6158(3) 0.1160(2) 0.0285(7) Uani 1 1 d . . . N3 N 0.3186(2) 0.1274(2) 1.17314(16) 0.0192(5) Uani 1 1 d . . . C4 C -0.0787(3) 0.6066(3) 0.0996(2) 0.0326(7) Uani 1 1 d . . . H4A H -0.1162 0.6741 0.0681 0.039 Uiso 1 1 calc R . . C5 C -0.1678(3) 0.4988(3) 0.1293(2) 0.0311(7) Uani 1 1 d . . . C6 C -0.1154(3) 0.3952(3) 0.1754(2) 0.0266(6) Uani 1 1 d . . . C7 C 0.0863(3) 0.2947(3) 0.2525(2) 0.0233(6) Uani 1 1 d . . . C8 C 0.5431(3) 0.4062(3) 0.3754(2) 0.0356(8) Uani 1 1 d . . . H8A H 0.4676 0.4469 0.3563 0.043 Uiso 1 1 calc R . . C9 C 0.6815(3) 0.4879(3) 0.4089(3) 0.0473(10) Uani 1 1 d . . . H9A H 0.6978 0.5819 0.4109 0.057 Uiso 1 1 calc R . . C10 C 0.7970(3) 0.4306(3) 0.4397(2) 0.0310(7) Uani 1 1 d . . . C11 C 0.7660(3) 0.2903(3) 0.4325(2) 0.0226(6) Uani 1 1 d . . . H11A H 0.8394 0.2470 0.4514 0.027 Uiso 1 1 calc R . . C12 C 0.6259(3) 0.2154(3) 0.3971(2) 0.0226(6) Uani 1 1 d . . . H12A H 0.6071 0.1211 0.3920 0.027 Uiso 1 1 calc R . . C13 C 0.9440(3) 0.5179(3) 0.4770(3) 0.0398(8) Uani 1 1 d . . . H13A H 0.9573 0.6092 0.4659 0.060 Uiso 1 1 calc R . . C14 C 0.2333(3) 0.1271(3) 0.7794(2) 0.0226(6) Uani 1 1 d . . . H14A H 0.1402 0.1115 0.7883 0.027 Uiso 1 1 calc R . . C15 C 0.2534(3) 0.1423(3) 0.6757(2) 0.0201(6) Uani 1 1 d . . . C16 C 0.3880(3) 0.1626(3) 0.6533(2) 0.0249(6) Uani 1 1 d . . . H16A H 0.4701 0.1704 0.7054 0.030 Uiso 1 1 calc R . . C17 C 0.3986(3) 0.1710(3) 0.5543(2) 0.0253(6) Uani 1 1 d . . . H17A H 0.4893 0.1840 0.5413 0.030 Uiso 1 1 calc R . . C18 C 0.1557(3) 0.1454(3) 0.4958(2) 0.0213(6) Uani 1 1 d . . . H18A H 0.0759 0.1410 0.4426 0.026 Uiso 1 1 calc R . . C19 C 0.1367(3) 0.1351(3) 0.5933(2) 0.0229(6) Uani 1 1 d . . . H19A H 0.0450 0.1233 0.6043 0.027 Uiso 1 1 calc R . . C20 C 0.4436(3) 0.1470(3) 1.1450(2) 0.0282(7) Uani 1 1 d . . . H20A H 0.5285 0.1616 1.1956 0.034 Uiso 1 1 calc R . . C21 C 0.4522(3) 0.1466(3) 1.0446(2) 0.0305(7) Uani 1 1 d . . . H21A H 0.5415 0.1607 1.0292 0.037 Uiso 1 1 calc R . . C22 C 0.3278(3) 0.1253(3) 0.9664(2) 0.0221(6) Uani 1 1 d . . . C23 C 0.1979(3) 0.1007(3) 0.9960(2) 0.0223(6) Uani 1 1 d . . . H23A H 0.1111 0.0819 0.9469 0.027 Uiso 1 1 calc R . . C24 C 0.1987(3) 0.1045(3) 1.0973(2) 0.0206(6) Uani 1 1 d . . . H24A H 0.1107 0.0903 1.1147 0.025 Uiso 1 1 calc R . . C25 C 0.3397(3) 0.1345(3) 0.8610(2) 0.0265(6) Uani 1 1 d . . . H25A H 0.4315 0.1467 0.8501 0.032 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 Ni1 0.01501(16) 0.02021(19) 0.01375(18) 0.00271(13) 0.00207(13) 0.00307(13) Cl1 0.0330(4) 0.0535(5) 0.0635(6) 0.0126(5) 0.0039(4) 0.0238(4) O1S 0.0215(9) 0.0264(10) 0.0232(11) 0.0026(8) 0.0039(8) 0.0060(8) O1 0.0175(9) 0.0240(10) 0.0238(10) 0.0032(8) -0.0001(8) 0.0048(8) N1 0.0190(11) 0.0233(12) 0.0161(12) 0.0022(9) 0.0014(9) 0.0031(9) N1S 0.0290(13) 0.0245(14) 0.0143(12) 0.0035(10) 0.0046(10) 0.0048(10) C1 0.0282(14) 0.0232(15) 0.0164(14) 0.0007(12) 0.0040(12) 0.0080(12) Cl2 0.0566(5) 0.0263(4) 0.0378(5) 0.0093(3) 0.0111(4) 0.0047(4) N2 0.0200(11) 0.0213(12) 0.0174(12) 0.0044(9) 0.0049(9) 0.0060(9) O2S 0.0176(9) 0.0277(11) 0.0222(10) 0.0042(8) 0.0049(8) 0.0039(8) O2 0.0236(10) 0.0341(12) 0.0476(14) 0.0195(10) 0.0043(9) 0.0050(9) C2 0.0266(14) 0.0277(16) 0.0197(15) -0.0032(12) 0.0009(12) 0.0075(12) Cl3 0.0269(4) 0.0416(5) 0.0511(5) 0.0203(4) 0.0096(3) 0.0048(3) O3S 0.0536(13) 0.0190(11) 0.0320(12) 0.0062(9) 0.0086(10) 0.0022(10) O3 0.0233(10) 0.0381(12) 0.0361(12) 0.0149(10) 0.0055(9) 0.0084(9) C3 0.0381(16) 0.0226(16) 0.0214(16) 0.0006(12) 0.0029(13) 0.0055(13) N3 0.0182(11) 0.0195(12) 0.0180(12) 0.0036(9) 0.0023(9) 0.0027(9) C4 0.0437(18) 0.0270(16) 0.0277(17) 0.0033(13) 0.0005(14) 0.0177(14) C5 0.0309(16) 0.0333(17) 0.0284(17) 0.0007(14) -0.0004(13) 0.0142(13) C6 0.0284(15) 0.0305(16) 0.0203(15) 0.0006(12) 0.0038(12) 0.0087(12) C7 0.0235(14) 0.0255(15) 0.0198(15) 0.0019(12) 0.0038(12) 0.0055(12) C8 0.0241(15) 0.0246(17) 0.052(2) 0.0032(15) -0.0056(14) 0.0084(12) C9 0.0262(16) 0.0212(17) 0.083(3) -0.0007(17) -0.0075(17) 0.0050(13) C10 0.0193(14) 0.0266(16) 0.0400(19) 0.0021(14) -0.0018(13) 0.0012(12) C11 0.0192(13) 0.0223(15) 0.0248(15) 0.0031(12) 0.0007(11) 0.0066(11) C12 0.0214(13) 0.0215(15) 0.0233(15) 0.0027(12) 0.0035(11) 0.0041(11) C13 0.0214(14) 0.0182(15) 0.068(2) 0.0036(15) -0.0080(15) 0.0003(12) C14 0.0245(14) 0.0250(15) 0.0189(15) 0.0040(12) 0.0074(12) 0.0053(11) C15 0.0250(13) 0.0165(14) 0.0192(15) 0.0023(11) 0.0065(11) 0.0049(11) C16 0.0231(14) 0.0348(17) 0.0182(15) 0.0049(12) 0.0021(11) 0.0128(12) C17 0.0210(14) 0.0343(17) 0.0212(16) 0.0047(13) 0.0038(12) 0.0095(12) C18 0.0186(13) 0.0247(15) 0.0177(14) 0.0002(12) 0.0015(11) 0.0033(11) C19 0.0195(13) 0.0280(15) 0.0184(15) 0.0015(12) 0.0036(11) 0.0020(11) C20 0.0206(14) 0.0437(18) 0.0187(15) 0.0039(13) 0.0018(12) 0.0082(13) C21 0.0209(14) 0.0466(19) 0.0253(16) 0.0041(14) 0.0072(12) 0.0094(13) C22 0.0250(13) 0.0248(15) 0.0162(14) 0.0027(12) 0.0046(11) 0.0064(11) C23 0.0212(13) 0.0223(14) 0.0199(15) 0.0015(12) 0.0012(11) 0.0027(11) C24 0.0181(13) 0.0216(14) 0.0200(15) 0.0015(11) 0.0039(11) 0.0018(11) C25 0.0239(14) 0.0362(17) 0.0211(15) 0.0046(13) 0.0088(12) 0.0073(12) _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 Ni1 O1 2.0221(18) . ? Ni1 N1 2.052(2) . ? Ni1 N3 2.085(2) 1_554 ? Ni1 N2 2.095(2) . ? Ni1 O1S 2.1174(18) . ? Ni1 O2S 2.1601(17) . ? Cl1 C5 1.738(3) . ? O1S N1S 1.279(3) . ? O1 C7 1.255(3) . ? N1 C8 1.327(4) . ? N1 C12 1.348(3) . ? N1S O3S 1.218(3) . ? N1S O2S 1.273(3) . ? C1 C2 1.409(4) . ? C1 C6 1.416(4) . ? C1 C7 1.503(4) . ? Cl2 C3 1.737(3) . ? N2 C18 1.343(3) . ? N2 C17 1.348(3) . ? O2 C7 1.268(3) . ? C2 C3 1.394(4) . ? C2 Cl3 1.730(3) . ? O3 C6 1.335(3) . ? O3 H3A 0.8200 . ? C3 C4 1.378(4) . ? N3 C24 1.343(3) . ? N3 C20 1.344(3) . ? N3 Ni1 2.085(2) 1_556 ? C4 C5 1.366(4) . ? C4 H4A 0.9300 . ? C5 C6 1.392(4) . ? C8 C9 1.379(4) . ? C8 H8A 0.9300 . ? C9 C10 1.392(4) . ? C9 H9A 0.9300 . ? C10 C11 1.382(4) . ? C10 C13 1.469(4) . ? C11 C12 1.372(3) . ? C11 H11A 0.9300 . ? C12 H12A 0.9300 . ? C13 C13 1.282(6) 2_766 ? C13 H13A 0.9300 . ? C14 C25 1.325(4) . ? C14 C15 1.470(4) . ? C14 H14A 0.9300 . ? C15 C19 1.394(4) . ? C15 C16 1.398(4) . ? C16 C17 1.371(4) . ? C16 H16A 0.9300 . ? C17 H17A 0.9300 . ? C18 C19 1.378(4) . ? C18 H18A 0.9300 . ? C19 H19A 0.9300 . ? C20 C21 1.379(4) . ? C20 H20A 0.9300 . ? C21 C22 1.392(4) . ? C21 H21A 0.9300 . ? C22 C23 1.397(4) . ? C22 C25 1.461(4) . ? C23 C24 1.367(4) . ? C23 H23A 0.9300 . ? C24 H24A 0.9300 . ? C25 H25A 0.9300 . ? 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 O1 Ni1 N1 94.66(8) . . ? O1 Ni1 N3 88.09(8) . 1_554 ? N1 Ni1 N3 92.52(8) . 1_554 ? O1 Ni1 N2 94.03(8) . . ? N1 Ni1 N2 91.01(8) . . ? N3 Ni1 N2 175.72(8) 1_554 . ? O1 Ni1 O1S 168.50(7) . . ? N1 Ni1 O1S 96.82(8) . . ? N3 Ni1 O1S 90.58(8) 1_554 . ? N2 Ni1 O1S 86.60(8) . . ? O1 Ni1 O2S 107.94(7) . . ? N1 Ni1 O2S 157.41(8) . . ? N3 Ni1 O2S 88.39(7) 1_554 . ? N2 Ni1 O2S 87.42(7) . . ? O1S Ni1 O2S 60.60(7) . . ? N1S O1S Ni1 92.75(14) . . ? C7 O1 Ni1 123.70(17) . . ? C8 N1 C12 117.5(2) . . ? C8 N1 Ni1 121.66(19) . . ? C12 N1 Ni1 120.82(17) . . ? O3S N1S O2S 122.6(2) . . ? O3S N1S O1S 121.8(2) . . ? O2S N1S O1S 115.5(2) . . ? C2 C1 C6 118.2(2) . . ? C2 C1 C7 124.4(2) . . ? C6 C1 C7 117.4(2) . . ? C18 N2 C17 116.9(2) . . ? C18 N2 Ni1 121.68(17) . . ? C17 N2 Ni1 121.11(17) . . ? N1S O2S Ni1 90.96(13) . . ? C3 C2 C1 120.4(3) . . ? C3 C2 Cl3 116.9(2) . . ? C1 C2 Cl3 122.7(2) . . ? C6 O3 H3A 109.5 . . ? C4 C3 C2 120.2(3) . . ? C4 C3 Cl2 117.7(2) . . ? C2 C3 Cl2 122.1(2) . . ? C24 N3 C20 116.3(2) . . ? C24 N3 Ni1 120.07(17) . 1_556 ? C20 N3 Ni1 123.32(18) . 1_556 ? C5 C4 C3 120.3(3) . . ? C5 C4 H4A 119.9 . . ? C3 C4 H4A 119.9 . . ? C4 C5 C6 121.2(3) . . ? C4 C5 Cl1 119.5(2) . . ? C6 C5 Cl1 119.3(2) . . ? O3 C6 C5 118.4(2) . . ? O3 C6 C1 122.0(3) . . ? C5 C6 C1 119.6(3) . . ? O1 C7 O2 122.9(3) . . ? O1 C7 C1 120.2(2) . . ? O2 C7 C1 117.0(2) . . ? N1 C8 C9 122.3(3) . . ? N1 C8 H8A 118.9 . . ? C9 C8 H8A 118.9 . . ? C8 C9 C10 120.5(3) . . ? C8 C9 H9A 119.8 . . ? C10 C9 H9A 119.8 . . ? C11 C10 C9 116.9(2) . . ? C11 C10 C13 122.7(3) . . ? C9 C10 C13 120.4(3) . . ? C12 C11 C10 119.4(3) . . ? C12 C11 H11A 120.3 . . ? C10 C11 H11A 120.3 . . ? N1 C12 C11 123.4(2) . . ? N1 C12 H12A 118.3 . . ? C11 C12 H12A 118.3 . . ? C13 C13 C10 127.2(4) 2_766 . ? C13 C13 H13A 116.4 2_766 . ? C10 C13 H13A 116.4 . . ? C25 C14 C15 124.0(2) . . ? C25 C14 H14A 118.0 . . ? C15 C14 H14A 118.0 . . ? C19 C15 C16 116.2(2) . . ? C19 C15 C14 121.0(2) . . ? C16 C15 C14 122.7(2) . . ? C17 C16 C15 119.8(2) . . ? C17 C16 H16A 120.1 . . ? C15 C16 H16A 120.1 . . ? N2 C17 C16 123.7(2) . . ? N2 C17 H17A 118.2 . . ? C16 C17 H17A 118.2 . . ? N2 C18 C19 122.6(2) . . ? N2 C18 H18A 118.7 . . ? C19 C18 H18A 118.7 . . ? C18 C19 C15 120.7(2) . . ? C18 C19 H19A 119.6 . . ? C15 C19 H19A 119.6 . . ? N3 C20 C21 123.3(2) . . ? N3 C20 H20A 118.4 . . ? C21 C20 H20A 118.4 . . ? C20 C21 C22 120.2(2) . . ? C20 C21 H21A 119.9 . . ? C22 C21 H21A 119.9 . . ? C21 C22 C23 116.2(2) . . ? C21 C22 C25 119.4(2) . . ? C23 C22 C25 124.3(2) . . ? C24 C23 C22 120.0(2) . . ? C24 C23 H23A 120.0 . . ? C22 C23 H23A 120.0 . . ? N3 C24 C23 124.0(2) . . ? N3 C24 H24A 118.0 . . ? C23 C24 H24A 118.0 . . ? C14 C25 C22 126.7(3) . . ? C14 C25 H25A 116.6 . . ? C22 C25 H25A 116.6 . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.78 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.530 _refine_diff_density_min -0.401 _refine_diff_density_rms 0.069