Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2004 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Dr Roy P Planalp' _publ_contact_author_address ; Department of Chemistry University of New Hampshire Parsons Hall Durham NH 03824 UNITED STATES OF AMERICA ; _publ_contact_author_email ROY.PLANALP@UNH.EDU _publ_section_title ; Nickel(II), Copper(II) and Zinc(II) Binding Properties and Cytotoxicity of Tripodal, Hexadentate Tris(ethylenediamine)-Analogue Chelators ; loop_ _publ_author_name 'Roy P. Planalp' 'Cary B. Bauer' 'Martin W. Brechbiel' 'Grant A. Broker' 'Thomas Clifford' ; R.Ma ; 'Gyungse Park' 'Ann M. Przyborowska' 'Robin Rogers' 'Paula E. Sloan' 'Suzy V. Torti' 'Neng Ye' data_rp31 _database_code_depnum_ccdc_archive 'CCDC 221223' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural 'RP31 (P286-005)' _chemical_formula_analytical ? _chemical_formula_sum 'C16 H40 Cl2 N6 Ni O9' _chemical_formula_weight 590.15 _chemical_melting_point ? _chemical_compound_source ? 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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 9.4038(6) _cell_length_b 13.7359(9) _cell_length_c 20.1269(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2599.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4474 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description parallelepiped _exptl_crystal_colour 'light purple' _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.508 _exptl_crystal_density_method ? _exptl_crystal_F_000 1248 _exptl_absorpt_coefficient_mu 1.007 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min 0.71 _exptl_absorpt_correction_T_max 0.97 _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_probe x-ray _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens P4' _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16425 _diffrn_reflns_av_R_equivalents 0.0683 _diffrn_reflns_av_sigmaI/netI 0.1014 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 27.92 _reflns_number_total 6063 _reflns_number_observed 4006 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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 fullcycle _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0427P)^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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0011(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.022(17) _refine_ls_number_reflns 6063 _refine_ls_number_parameters 342 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1064 _refine_ls_R_factor_gt 0.0561 _refine_ls_wR_factor_ref 0.1048 _refine_ls_wR_factor_gt 0.0907 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _refine_ls_shift/su_max 0.440 _refine_ls_shift/su_mean 0.020 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 Ni Ni 0.36227(6) 0.02089(4) 0.35976(3) 0.02438(14) Uani 1 1 d . . . Cl1 Cl 0.70812(13) -0.26367(8) 0.34496(5) 0.0344(3) Uani 1 1 d . . . Cl2 Cl -0.30665(14) 0.24567(9) 0.42405(6) 0.0414(3) Uani 1 1 d . . . O1 O 0.8141(4) -0.3195(3) 0.31133(19) 0.0639(11) Uani 1 1 d . A . O2A O 0.6450(8) -0.2035(4) 0.2967(3) 0.107(3) Uani 0.75 1 d P A 1 O3A O 0.7622(6) -0.2067(5) 0.3976(3) 0.098(2) Uani 0.75 1 d P A 1 O4A O 0.5982(6) -0.3230(4) 0.3699(3) 0.094(2) Uani 0.75 1 d P A 1 O2B O 0.584(2) -0.2719(15) 0.3181(10) 0.114(7) Uiso 0.25 1 d P A 2 O3B O 0.749(2) -0.1705(16) 0.3440(11) 0.114(7) Uiso 0.25 1 d P A 2 O4B O 0.725(3) -0.2726(17) 0.4119(12) 0.128(8) Uiso 0.25 1 d P A 2 O5 O -0.4433(5) 0.2837(3) 0.4381(3) 0.1058(19) Uani 1 1 d . . . O6 O -0.2901(5) 0.1596(3) 0.4613(2) 0.0937(16) Uani 1 1 d . . . O7 O -0.2001(4) 0.3159(3) 0.44137(19) 0.0631(11) Uani 1 1 d . . . O8 O -0.2963(5) 0.2209(3) 0.35692(19) 0.0880(15) Uani 1 1 d . . . O9 O -0.4322(5) 0.4842(3) 0.48086(18) 0.0759(13) Uani 1 1 d . . . H9O H -0.4234 0.4434 0.4457 0.091 Uiso 1 1 d R . . N1 N 0.3243(3) -0.0119(2) 0.25855(16) 0.0307(9) Uani 1 1 d . . . H1N H 0.2802 0.0425 0.2494 0.037 Uiso 1 1 d R . . N2 N 0.3667(4) -0.1287(2) 0.38406(16) 0.0310(9) Uani 1 1 d . . . H2N H 0.4333 -0.1574 0.3642 0.037 Uiso 1 1 d R . . N3 N 0.1425(4) 0.0259(2) 0.37748(16) 0.0304(8) Uani 1 1 d . . . H3N H 0.1304 0.0221 0.4265 0.037 Uiso 1 1 d R . . N4 N 0.5770(3) 0.0236(3) 0.32629(15) 0.0290(8) Uani 1 1 d . . . H4AN H 0.6454 0.0825 0.3368 0.035 Uiso 1 1 d R . . H4BN H 0.5885 -0.0574 0.3185 0.035 Uiso 1 1 d R . . N5 N 0.4249(4) 0.0349(2) 0.46093(15) 0.0280(9) Uani 1 1 d . . . H5AN H 0.3579 0.0410 0.4919 0.034 Uiso 1 1 d R . . H5BN H 0.4993 0.1021 0.4731 0.034 Uiso 1 1 d R . . N6 N 0.3335(3) 0.1737(2) 0.34990(16) 0.0260(8) Uani 1 1 d . . . H6AN H 0.3227 0.2025 0.3059 0.031 Uiso 1 1 d R . . H6BN H 0.4105 0.2022 0.3627 0.031 Uiso 1 1 d R . . C1 C 0.2191(5) -0.0914(3) 0.2471(2) 0.0393(12) Uani 1 1 d . . . H1A H 0.2129 -0.1031 0.1981 0.047 Uiso 1 1 calc R . . C2 C 0.2588(5) -0.1868(3) 0.2801(2) 0.0393(12) Uani 1 1 d . . . H2A H 0.3577 -0.2034 0.2675 0.047 Uiso 1 1 calc R . . H2B H 0.1963 -0.2387 0.2624 0.047 Uiso 1 1 calc R . . C3 C 0.2480(5) -0.1871(3) 0.3563(3) 0.0392(11) Uani 1 1 d . . . H3A H 0.2588 -0.2558 0.3721 0.047 Uiso 1 1 calc R . . C4 C 0.1013(5) -0.1503(3) 0.3777(3) 0.0459(14) Uani 1 1 d . . . H4B' H 0.0296 -0.2000 0.3657 0.055 Uiso 1 1 calc R . . H4C H 0.1006 -0.1436 0.4267 0.055 Uiso 1 1 calc R . . C5 C 0.0571(5) -0.0539(3) 0.3474(3) 0.0424(13) Uani 1 1 d . . . H5B' H -0.0454 -0.0424 0.3580 0.051 Uiso 1 1 calc R . . C6 C 0.0739(5) -0.0585(4) 0.2711(3) 0.0484(14) Uani 1 1 d . . . H6B' H 0.0013 -0.1036 0.2531 0.058 Uiso 1 1 calc R . . H6C H 0.0543 0.0069 0.2526 0.058 Uiso 1 1 calc R . . C7 C 0.4612(5) -0.0241(3) 0.2238(2) 0.0365(11) Uani 1 1 d . . . H7A H 0.4493 -0.0092 0.1760 0.044 Uiso 1 1 calc R . . H7B H 0.4940 -0.0923 0.2279 0.044 Uiso 1 1 calc R . . C8 C 0.5703(5) 0.0438(3) 0.2539(2) 0.0288(11) Uani 1 1 d . . . H8A H 0.5359 0.1121 0.2478 0.035 Uiso 1 1 calc R . . C9 C 0.7152(5) 0.0346(4) 0.2198(2) 0.0470(13) Uani 1 1 d . . . H9A H 0.7826 0.0798 0.2405 0.070 Uiso 1 1 calc R . . H9B H 0.7053 0.0504 0.1726 0.070 Uiso 1 1 calc R . . H9C H 0.7502 -0.0322 0.2245 0.070 Uiso 1 1 calc R . . C10 C 0.3865(6) -0.1391(3) 0.4567(2) 0.0385(12) Uani 1 1 d . . . H10A H 0.4264 -0.2041 0.4668 0.046 Uiso 1 1 calc R . . H10B H 0.2936 -0.1332 0.4794 0.046 Uiso 1 1 calc R . . C11 C 0.4866(5) -0.0607(3) 0.4815(2) 0.0337(12) Uani 1 1 d . . . H11A H 0.5803 -0.0690 0.4587 0.040 Uiso 1 1 calc R . . C12 C 0.5106(6) -0.0681(4) 0.5559(2) 0.0500(15) Uani 1 1 d . . . H12A H 0.5722 -0.0147 0.5705 0.075 Uiso 1 1 calc R . . H12B H 0.5561 -0.1305 0.5662 0.075 Uiso 1 1 calc R . . H12C H 0.4191 -0.0640 0.5790 0.075 Uiso 1 1 calc R . . C13 C 0.0902(5) 0.1245(3) 0.3619(3) 0.0354(11) Uani 1 1 d . . . H13A H -0.0003 0.1366 0.3857 0.043 Uiso 1 1 calc R . . H13B H 0.0720 0.1302 0.3136 0.043 Uiso 1 1 calc R . . C14 C 0.1986(5) 0.1981(3) 0.3826(2) 0.0301(11) Uani 1 1 d . . . H14A H 0.2132 0.1907 0.4316 0.036 Uiso 1 1 calc R . . C15 C 0.1508(5) 0.3023(3) 0.3700(2) 0.0430(12) Uani 1 1 d . . . H15A H 0.2233 0.3475 0.3866 0.065 Uiso 1 1 calc R . . H15B H 0.0608 0.3143 0.3932 0.065 Uiso 1 1 calc R . . H15C H 0.1376 0.3124 0.3222 0.065 Uiso 1 1 calc R . . C16 C -0.5727(7) 0.5238(5) 0.4743(3) 0.079(2) Uani 1 1 d . . . H16A H -0.6419 0.4705 0.4720 0.119 Uiso 1 1 calc R . . H16B H -0.5783 0.5628 0.4337 0.119 Uiso 1 1 calc R . . H16C H -0.5939 0.5650 0.5128 0.119 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 Ni 0.0248(3) 0.0209(2) 0.0274(3) -0.0019(2) -0.0021(3) 0.0013(3) Cl1 0.0343(7) 0.0305(6) 0.0383(7) -0.0041(5) -0.0055(5) 0.0010(5) Cl2 0.0415(8) 0.0471(8) 0.0357(7) -0.0065(6) 0.0016(6) -0.0129(6) O1 0.055(3) 0.069(3) 0.068(3) -0.021(2) -0.005(2) 0.030(2) O2A 0.161(6) 0.101(5) 0.059(4) 0.044(3) 0.026(4) 0.104(5) O3A 0.051(4) 0.154(6) 0.088(4) -0.096(4) 0.005(3) -0.031(4) O4A 0.102(5) 0.054(3) 0.126(5) -0.013(3) 0.069(4) -0.050(3) O5 0.039(3) 0.092(4) 0.187(5) -0.077(4) -0.008(3) 0.002(2) O6 0.110(4) 0.081(3) 0.089(3) 0.039(3) -0.031(3) -0.031(3) O7 0.052(3) 0.070(3) 0.067(3) -0.021(2) 0.002(2) -0.028(2) O8 0.145(4) 0.072(3) 0.047(2) -0.018(2) 0.018(3) -0.063(3) O9 0.090(3) 0.074(3) 0.064(3) -0.007(2) -0.029(2) 0.019(3) N1 0.029(2) 0.025(2) 0.038(2) -0.0049(16) -0.0103(16) 0.0042(17) N2 0.037(2) 0.0211(18) 0.035(2) -0.0016(15) -0.003(2) 0.0019(18) N3 0.0265(19) 0.0243(17) 0.040(2) -0.0035(17) -0.0010(17) -0.005(2) N4 0.031(2) 0.0259(18) 0.0302(19) -0.0031(17) -0.0004(16) -0.0048(18) N5 0.038(2) 0.021(2) 0.0252(19) 0.0009(16) 0.0031(16) 0.0051(17) N6 0.023(2) 0.0274(18) 0.027(2) 0.0009(15) 0.0005(17) -0.0011(15) C1 0.042(3) 0.038(3) 0.038(3) -0.011(2) -0.014(2) 0.000(2) C2 0.042(3) 0.030(3) 0.046(3) -0.010(2) -0.011(2) -0.007(2) C3 0.042(3) 0.020(2) 0.056(3) -0.004(2) -0.006(3) -0.009(2) C4 0.039(4) 0.036(3) 0.063(4) -0.002(2) -0.004(3) -0.013(2) C5 0.026(3) 0.046(3) 0.055(4) -0.004(3) -0.002(3) -0.004(2) C6 0.035(3) 0.042(3) 0.068(4) -0.010(3) -0.018(3) -0.010(2) C7 0.040(3) 0.035(3) 0.035(3) -0.001(2) 0.003(2) 0.010(3) C8 0.029(3) 0.023(3) 0.034(3) -0.0012(19) -0.002(2) 0.0048(19) C9 0.049(3) 0.046(3) 0.046(3) -0.002(3) 0.018(3) 0.008(3) C10 0.051(4) 0.025(2) 0.039(3) 0.008(2) -0.002(3) 0.005(2) C11 0.038(3) 0.027(2) 0.036(3) 0.008(2) -0.003(2) 0.003(2) C12 0.073(4) 0.043(3) 0.035(3) 0.010(2) -0.014(3) -0.002(3) C13 0.031(3) 0.036(3) 0.040(3) 0.002(2) 0.003(2) 0.010(2) C14 0.039(3) 0.022(2) 0.030(2) 0.0011(18) -0.001(2) 0.006(2) C15 0.043(3) 0.030(2) 0.056(3) 0.007(2) 0.004(3) 0.015(2) C16 0.071(5) 0.104(5) 0.063(4) -0.007(4) -0.021(3) 0.006(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 Ni N3 2.098(4) . ? Ni N2 2.113(3) . ? Ni N1 2.117(3) . ? Ni N6 2.125(3) . ? Ni N4 2.129(3) . ? Ni N5 2.129(3) . ? Cl1 O2B 1.29(2) . ? Cl1 O3B 1.34(2) . ? Cl1 O4B 1.36(2) . ? Cl1 O2A 1.407(4) . ? Cl1 O4A 1.409(5) . ? Cl1 O3A 1.411(5) . ? Cl1 O1 1.428(3) . ? Cl2 O8 1.397(4) . ? Cl2 O6 1.408(4) . ? Cl2 O5 1.416(4) . ? Cl2 O7 1.434(4) . ? O9 C16 1.435(7) . ? N1 C7 1.475(5) . ? N1 C1 1.491(5) . ? N2 C10 1.480(5) . ? N2 C3 1.484(5) . ? N3 C13 1.475(5) . ? N3 C5 1.488(5) . ? N4 C8 1.484(5) . ? N5 C11 1.494(5) . ? N6 C14 1.468(5) . ? C1 C2 1.516(6) . ? C1 C6 1.518(6) . ? C2 C3 1.536(7) . ? C3 C4 1.531(6) . ? C4 C5 1.516(6) . ? C5 C6 1.545(7) . ? C7 C8 1.513(6) . ? C8 C9 1.531(6) . ? C10 C11 1.515(6) . ? C11 C12 1.518(6) . ? C13 C14 1.494(6) . ? C14 C15 1.522(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N3 Ni N2 90.69(14) . . ? N3 Ni N1 90.25(13) . . ? N2 Ni N1 91.10(13) . . ? N3 Ni N6 81.84(13) . . ? N2 Ni N6 169.92(13) . . ? N1 Ni N6 95.67(13) . . ? N3 Ni N4 170.88(13) . . ? N2 Ni N4 94.11(15) . . ? N1 Ni N4 81.91(13) . . ? N6 Ni N4 94.24(13) . . ? N3 Ni N5 96.15(13) . . ? N2 Ni N5 82.00(13) . . ? N1 Ni N5 170.63(13) . . ? N6 Ni N5 92.03(13) . . ? N4 Ni N5 92.20(13) . . ? O2B Cl1 O3B 109.7(13) . . ? O2B Cl1 O4B 121.0(14) . . ? O3B Cl1 O4B 93.8(13) . . ? O2B Cl1 O2A 51.7(9) . . ? O3B Cl1 O2A 63.2(9) . . ? O4B Cl1 O2A 141.8(10) . . ? O2B Cl1 O4A 55.7(9) . . ? O3B Cl1 O4A 140.4(9) . . ? O4B Cl1 O4A 71.5(10) . . ? O2A Cl1 O4A 106.1(4) . . ? O2B Cl1 O3A 133.6(9) . . ? O3B Cl1 O3A 51.4(9) . . ? O4B Cl1 O3A 42.7(10) . . ? O2A Cl1 O3A 110.1(4) . . ? O4A Cl1 O3A 108.5(4) . . ? O2B Cl1 O1 112.6(9) . . ? O3B Cl1 O1 107.9(9) . . ? O4B Cl1 O1 109.7(10) . . ? O2A Cl1 O1 106.4(3) . . ? O4A Cl1 O1 111.7(3) . . ? O3A Cl1 O1 113.7(3) . . ? O8 Cl2 O6 107.6(3) . . ? O8 Cl2 O5 110.3(3) . . ? O6 Cl2 O5 107.7(3) . . ? O8 Cl2 O7 110.5(2) . . ? O6 Cl2 O7 111.0(3) . . ? O5 Cl2 O7 109.7(3) . . ? C7 N1 C1 115.0(3) . . ? C7 N1 Ni 109.5(2) . . ? C1 N1 Ni 114.7(3) . . ? C10 N2 C3 114.5(4) . . ? C10 N2 Ni 108.9(2) . . ? C3 N2 Ni 115.1(3) . . ? C13 N3 C5 114.2(4) . . ? C13 N3 Ni 108.8(2) . . ? C5 N3 Ni 116.0(3) . . ? C8 N4 Ni 105.9(2) . . ? C11 N5 Ni 107.1(3) . . ? C14 N6 Ni 107.1(2) . . ? N1 C1 C2 113.7(4) . . ? N1 C1 C6 109.2(4) . . ? C2 C1 C6 109.8(4) . . ? C1 C2 C3 115.1(4) . . ? N2 C3 C4 113.1(4) . . ? N2 C3 C2 108.9(4) . . ? C4 C3 C2 109.9(4) . . ? C5 C4 C3 115.0(4) . . ? N3 C5 C4 109.4(4) . . ? N3 C5 C6 112.3(4) . . ? C4 C5 C6 109.6(4) . . ? C1 C6 C5 114.9(4) . . ? N1 C7 C8 109.4(3) . . ? N4 C8 C7 107.9(3) . . ? N4 C8 C9 112.8(3) . . ? C7 C8 C9 111.9(4) . . ? N2 C10 C11 109.6(4) . . ? N5 C11 C10 107.0(4) . . ? N5 C11 C12 113.0(4) . . ? C10 C11 C12 111.7(4) . . ? N3 C13 C14 109.5(4) . . ? N6 C14 C13 108.1(3) . . ? N6 C14 C15 113.3(4) . . ? C13 C14 C15 112.8(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 C2 C3 C4 51.7(5) . . . . ? C2 C3 C4 C5 -51.6(5) . . . . ? C3 C4 C5 C6 51.8(5) . . . . ? C4 C5 C6 C1 -52.5(5) . . . . ? C5 C6 C1 C2 52.6(5) . . . . ? C6 C1 C2 C3 -52.3(5) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.92 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.421 _refine_diff_density_min -0.433 _refine_diff_density_rms 0.077 data_rp13s _database_code_depnum_ccdc_archive 'CCDC 221224' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety RP13 _chemical_formula_sum 'C33 H48 Cl2 Cu N6 O8' _chemical_formula_weight 791.21 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 13.3903(11) _cell_length_b 16.0536(12) _cell_length_c 17.8755(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3842.6(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2835 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour blue _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.368 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1660 _exptl_absorpt_coefficient_mu 0.762 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_probe x-ray _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens P4' _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2027 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0817 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 19.93 _reflns_number_total 2027 _reflns_number_gt 1501 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens 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^)+(0.0472P)^2^+4.6130P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.32(4) _refine_ls_number_reflns 2027 _refine_ls_number_parameters 454 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0905 _refine_ls_R_factor_gt 0.0519 _refine_ls_wR_factor_ref 0.1172 _refine_ls_wR_factor_gt 0.1009 _refine_ls_goodness_of_fit_ref 1.107 _refine_ls_restrained_S_all 1.107 _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 Cu Cu -0.10749(12) 0.84603(9) 0.65526(9) 0.0365(5) Uani 1 1 d . . . Cl1 Cl 0.5983(3) 0.3937(2) 0.3271(2) 0.0494(10) Uani 1 1 d . . . Cl2 Cl 0.1676(3) 0.6937(3) 0.5617(2) 0.0566(12) Uani 1 1 d . . . O1 O 0.5386(10) 0.4073(10) 0.2657(7) 0.121(5) Uani 1 1 d . . . O2 O 0.5413(11) 0.3456(9) 0.3771(9) 0.152(6) Uani 1 1 d . . . O3 O 0.6160(9) 0.4675(6) 0.3636(7) 0.106(4) Uani 1 1 d . . . O4 O 0.6861(9) 0.3513(7) 0.3075(6) 0.094(4) Uani 1 1 d . . . O5 O 0.2580(8) 0.7366(7) 0.5807(6) 0.091(4) Uani 1 1 d . . . O6 O 0.1888(8) 0.6281(6) 0.5109(6) 0.074(3) Uani 1 1 d . . . O7 O 0.1003(9) 0.7502(7) 0.5256(6) 0.093(4) Uani 1 1 d . . . O8 O 0.1209(8) 0.6651(6) 0.6296(5) 0.072(3) Uani 1 1 d . . . N1 N -0.1337(7) 0.9753(6) 0.6608(6) 0.036(3) Uani 1 1 d . . . H1N1 H -0.0739 0.9983 0.6773 0.044 Uiso 1 1 calc R . . N2 N -0.1014(8) 0.8397(6) 0.7806(5) 0.043(3) Uani 1 1 d . . . H1N2 H -0.1120 0.7844 0.7938 0.052 Uiso 1 1 calc R . . N3 N -0.2591(6) 0.8256(5) 0.6551(6) 0.032(3) Uani 1 1 d . . . H1N3 H -0.2829 0.8457 0.6096 0.038 Uiso 1 1 calc R . . N4 N -0.0884(8) 0.8815(5) 0.5296(5) 0.040(3) Uani 1 1 d . . . H1N4 H -0.0321 0.8568 0.5102 0.048 Uiso 1 1 calc R . . H2N4 H -0.1429 0.8640 0.5024 0.048 Uiso 1 1 calc R . . N5 N 0.0453(7) 0.8552(7) 0.6730(6) 0.044(3) Uani 1 1 d . . . H1N5 H 0.0781 0.8241 0.6375 0.053 Uiso 1 1 calc R . . H2N5 H 0.0645 0.9098 0.6672 0.053 Uiso 1 1 calc R . . N6 N -0.1005(8) 0.7198(5) 0.6301(5) 0.031(3) Uani 1 1 d . . . H1N6 H -0.0538 0.7103 0.5934 0.037 Uiso 1 1 calc R . . H2N6 H -0.0828 0.6898 0.6719 0.037 Uiso 1 1 calc R . . C1 C -0.2098(10) 1.0036(8) 0.7152(8) 0.043(4) Uani 1 1 d . . . H1A H -0.2154 1.0656 0.7119 0.051 Uiso 1 1 calc R . . C2 C -0.1787(11) 0.9812(8) 0.7921(8) 0.048(4) Uani 1 1 d . . . H2A H -0.2205 1.0135 0.8273 0.058 Uiso 1 1 calc R . . H2B H -0.1089 1.0001 0.7989 0.058 Uiso 1 1 calc R . . C3 C -0.1840(11) 0.8893(8) 0.8155(8) 0.047(4) Uani 1 1 d . . . H3A H -0.1768 0.8861 0.8711 0.056 Uiso 1 1 calc R . . C4 C -0.2830(10) 0.8519(9) 0.7942(8) 0.048(4) Uani 1 1 d . . . H4B H -0.3345 0.8729 0.8292 0.058 Uiso 1 1 calc R . . H4C H -0.2789 0.7907 0.8008 0.058 Uiso 1 1 calc R . . C5 C -0.3168(11) 0.8699(8) 0.7150(8) 0.050(4) Uani 1 1 d . . . H5B H -0.3881 0.8520 0.7108 0.060 Uiso 1 1 calc R . . C6 C -0.3130(10) 0.9653(8) 0.6995(8) 0.049(4) Uani 1 1 d . . . H6B H -0.3309 0.9756 0.6466 0.059 Uiso 1 1 calc R . . H6C H -0.3634 0.9935 0.7312 0.059 Uiso 1 1 calc R . . C7 C -0.1488(10) 1.0087(8) 0.5859(8) 0.044(5) Uani 1 1 d . . . H7A H -0.1397 1.0699 0.5877 0.052 Uiso 1 1 calc R . . H7B H -0.2187 0.9978 0.5707 0.052 Uiso 1 1 calc R . . C8 C -0.0794(10) 0.9734(8) 0.5262(7) 0.044(4) Uani 1 1 d . . . H8A H -0.0092 0.9892 0.5388 0.052 Uiso 1 1 calc R . . C9 C -0.1070(12) 1.0129(8) 0.4511(7) 0.047(4) Uani 1 1 d . . . H9A H -0.1787 1.0028 0.4411 0.056 Uiso 1 1 calc R . . H9B H -0.0969 1.0738 0.4544 0.056 Uiso 1 1 calc R . . C10 C -0.0471(11) 0.9796(12) 0.3876(9) 0.048(4) Uani 1 1 d . . . C11 C 0.0308(13) 1.0287(11) 0.3584(11) 0.066(5) Uani 1 1 d . . . H11A H 0.0440 1.0814 0.3803 0.080 Uiso 1 1 calc R . . C12 C 0.0881(13) 1.0028(14) 0.2994(12) 0.076(6) Uani 1 1 d . . . H12A H 0.1410 1.0371 0.2818 0.091 Uiso 1 1 calc R . . C13 C 0.0695(14) 0.9275(14) 0.2653(9) 0.072(6) Uani 1 1 d . . . H13A H 0.1088 0.9098 0.2240 0.087 Uiso 1 1 calc R . . C14 C -0.0072(12) 0.8778(10) 0.2921(9) 0.053(4) Uani 1 1 d . . . H14A H -0.0211 0.8256 0.2694 0.063 Uiso 1 1 calc R . . C15 C -0.0636(10) 0.9053(10) 0.3525(9) 0.045(4) Uani 1 1 d . . . H15A H -0.1162 0.8708 0.3701 0.054 Uiso 1 1 calc R . . C16 C 0.0007(10) 0.8600(9) 0.8020(8) 0.052(4) Uani 1 1 d . . . H16A H 0.0142 0.8371 0.8524 0.062 Uiso 1 1 calc R . . H16B H 0.0080 0.9213 0.8047 0.062 Uiso 1 1 calc R . . C17 C 0.0753(9) 0.8261(8) 0.7483(8) 0.039(4) Uani 1 1 d . . . H17A H 0.0699 0.7640 0.7491 0.047 Uiso 1 1 calc R . . C18 C 0.1828(10) 0.8489(10) 0.7636(8) 0.054(4) Uani 1 1 d . . . H18A H 0.2229 0.8345 0.7189 0.065 Uiso 1 1 calc R . . H18B H 0.1868 0.9100 0.7703 0.065 Uiso 1 1 calc R . . C19 C 0.2296(10) 0.8083(10) 0.8301(9) 0.050(4) Uani 1 1 d . . . C20 C 0.2240(12) 0.8397(12) 0.9020(10) 0.074(5) Uani 1 1 d . . . H20A H 0.1855 0.8884 0.9109 0.089 Uiso 1 1 calc R . . C21 C 0.2719(14) 0.8030(15) 0.9601(11) 0.091(6) Uani 1 1 d . . . H21A H 0.2669 0.8273 1.0084 0.109 Uiso 1 1 calc R . . C22 C 0.3272(14) 0.7322(14) 0.9512(13) 0.094(7) Uani 1 1 d . . . H22A H 0.3604 0.7068 0.9923 0.113 Uiso 1 1 calc R . . C23 C 0.3329(12) 0.6990(10) 0.8800(13) 0.072(5) Uani 1 1 d . . . H23 H 0.3715 0.6502 0.8717 0.087 Uiso 1 1 calc R . . C24 C 0.2841(11) 0.7351(10) 0.8215(10) 0.060(5) Uani 1 1 d . . . H24A H 0.2873 0.7096 0.7736 0.072 Uiso 1 1 calc R . . C25 C -0.2780(9) 0.7354(7) 0.6551(8) 0.039(4) Uani 1 1 d . . . H25A H -0.3468 0.7240 0.6375 0.047 Uiso 1 1 calc R . . H25B H -0.2710 0.7130 0.7065 0.047 Uiso 1 1 calc R . . C26 C -0.2028(9) 0.6938(8) 0.6034(8) 0.037(4) Uani 1 1 d . . . H26A H -0.2128 0.7162 0.5518 0.044 Uiso 1 1 calc R . . C27 C -0.2172(10) 0.6002(8) 0.6011(8) 0.043(4) Uani 1 1 d . . . H27A H -0.2007 0.5770 0.6509 0.052 Uiso 1 1 calc R . . H27B H -0.2886 0.5883 0.5914 0.052 Uiso 1 1 calc R . . C28 C -0.1569(11) 0.5571(9) 0.5446(9) 0.040(4) Uiso 1 1 d . . . C29 C -0.1966(11) 0.5388(9) 0.4740(10) 0.060(5) Uani 1 1 d . . . H29A H -0.2634 0.5546 0.4630 0.073 Uiso 1 1 calc R . . C30 C -0.1430(14) 0.4995(12) 0.4216(11) 0.092(7) Uani 1 1 d . . . H30A H -0.1723 0.4879 0.3744 0.111 Uiso 1 1 calc R . . C31 C -0.0466(14) 0.4760(11) 0.4351(12) 0.076(6) Uani 1 1 d . . . H31A H -0.0097 0.4463 0.3985 0.092 Uiso 1 1 calc R . . C32 C -0.0050(12) 0.4957(9) 0.5012(12) 0.064(5) Uani 1 1 d . . . H32A H 0.0630 0.4822 0.5103 0.077 Uiso 1 1 calc R . . C33 C -0.0596(11) 0.5350(8) 0.5555(9) 0.045(4) Uani 1 1 d . . . H33A H -0.0288 0.5472 0.6021 0.054 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 Cu 0.0380(9) 0.0306(9) 0.0408(10) -0.0044(10) -0.0017(10) 0.0027(9) Cl1 0.060(3) 0.039(2) 0.049(3) -0.008(2) -0.001(3) 0.006(2) Cl2 0.049(3) 0.062(3) 0.058(3) 0.007(3) 0.016(3) 0.008(2) O1 0.100(11) 0.190(15) 0.074(10) -0.022(10) -0.032(8) 0.056(10) O2 0.148(13) 0.111(11) 0.196(17) 0.032(13) 0.051(12) -0.030(11) O3 0.095(9) 0.062(7) 0.160(13) -0.054(9) -0.026(10) 0.013(8) O4 0.085(9) 0.091(8) 0.105(10) -0.043(8) 0.006(7) 0.048(8) O5 0.071(8) 0.111(10) 0.090(10) -0.010(8) 0.008(7) -0.020(8) O6 0.068(8) 0.071(8) 0.083(8) -0.016(7) 0.022(7) 0.009(6) O7 0.087(8) 0.110(8) 0.081(9) 0.032(8) 0.012(8) 0.056(9) O8 0.088(8) 0.071(7) 0.058(7) -0.002(7) 0.024(7) 0.003(7) N1 0.056(8) 0.031(6) 0.021(7) 0.004(6) -0.011(7) -0.002(5) N2 0.043(7) 0.037(6) 0.049(7) -0.006(6) -0.012(7) -0.013(7) N3 0.031(6) 0.026(7) 0.039(7) -0.013(6) -0.011(6) 0.002(5) N4 0.047(8) 0.034(7) 0.039(7) 0.006(6) -0.002(6) -0.002(6) N5 0.057(7) 0.041(7) 0.034(8) 0.002(7) -0.008(6) -0.010(6) N6 0.033(6) 0.022(5) 0.038(7) 0.007(5) -0.004(6) 0.006(6) C1 0.055(11) 0.031(9) 0.042(11) -0.008(9) 0.007(9) 0.017(8) C2 0.066(11) 0.043(10) 0.035(10) -0.011(9) -0.005(9) 0.013(8) C3 0.055(11) 0.050(10) 0.035(10) 0.003(8) 0.014(8) 0.016(9) C4 0.056(11) 0.045(9) 0.044(11) 0.006(10) 0.012(8) -0.007(9) C5 0.052(10) 0.049(11) 0.048(11) -0.009(9) 0.021(9) 0.013(8) C6 0.033(10) 0.059(11) 0.054(11) -0.005(9) 0.010(8) 0.018(8) C7 0.044(11) 0.023(8) 0.064(13) -0.005(9) -0.021(9) -0.004(7) C8 0.052(11) 0.042(10) 0.037(10) 0.005(9) -0.001(8) -0.007(8) C9 0.058(10) 0.047(9) 0.035(9) 0.023(8) -0.009(10) -0.019(9) C10 0.029(10) 0.068(12) 0.045(12) 0.030(11) -0.005(9) 0.013(10) C11 0.048(12) 0.080(12) 0.072(15) 0.022(13) -0.012(11) 0.007(11) C12 0.040(12) 0.104(17) 0.084(16) 0.040(14) 0.004(12) 0.015(12) C13 0.082(17) 0.107(16) 0.027(11) 0.032(13) 0.008(10) 0.044(13) C14 0.064(12) 0.064(12) 0.030(11) 0.019(10) -0.005(9) 0.021(10) C15 0.054(11) 0.059(11) 0.021(9) 0.019(10) 0.004(9) 0.000(8) C16 0.052(12) 0.051(10) 0.052(11) 0.008(10) -0.015(9) 0.005(9) C17 0.040(11) 0.030(9) 0.047(10) 0.002(8) -0.019(8) -0.013(7) C18 0.056(11) 0.051(9) 0.056(11) 0.011(10) -0.006(9) -0.010(9) C19 0.039(9) 0.067(11) 0.044(12) -0.002(11) -0.017(9) -0.003(9) C20 0.076(13) 0.081(13) 0.065(14) -0.025(14) -0.034(11) 0.015(11) C21 0.082(15) 0.133(19) 0.058(15) -0.011(14) -0.031(12) 0.015(14) C22 0.079(15) 0.106(18) 0.097(19) 0.037(16) -0.033(14) 0.017(14) C23 0.066(12) 0.053(11) 0.098(16) -0.004(13) -0.035(13) 0.010(10) C24 0.040(10) 0.072(12) 0.069(14) -0.029(11) -0.012(10) 0.014(9) C25 0.050(9) 0.035(8) 0.033(9) -0.015(9) 0.020(8) -0.004(7) C26 0.040(10) 0.036(9) 0.034(9) -0.012(8) -0.008(8) -0.010(7) C27 0.053(10) 0.031(10) 0.045(11) -0.006(9) -0.004(8) 0.000(8) C29 0.039(10) 0.063(11) 0.079(14) -0.021(11) -0.007(10) 0.023(9) C30 0.060(16) 0.130(18) 0.087(16) -0.057(14) 0.005(12) 0.030(12) C31 0.053(14) 0.077(13) 0.099(17) -0.049(13) 0.011(13) 0.014(11) C32 0.056(13) 0.036(11) 0.102(17) -0.004(11) -0.013(13) -0.013(9) C33 0.064(12) 0.026(8) 0.046(11) -0.012(9) -0.007(9) 0.011(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 Cu N3 2.057(9) . ? Cu N5 2.075(10) . ? Cu N6 2.078(8) . ? Cu N1 2.107(9) . ? Cu N2 2.245(9) . ? Cu N4 2.331(9) . ? Cl1 O3 1.373(10) . ? Cl1 O1 1.376(11) . ? Cl1 O4 1.403(10) . ? Cl1 O2 1.405(14) . ? Cl2 O6 1.419(10) . ? Cl2 O7 1.433(10) . ? Cl2 O5 1.434(11) . ? Cl2 O8 1.440(9) . ? N1 C7 1.457(15) . ? N1 C1 1.480(15) . ? N2 C16 1.456(15) . ? N2 C3 1.498(15) . ? N3 C25 1.470(13) . ? N3 C5 1.500(15) . ? N4 C8 1.481(15) . ? N5 C17 1.480(15) . ? N6 C26 1.508(15) . ? C1 C2 1.479(18) . ? C1 C6 1.538(17) . ? C2 C3 1.535(17) . ? C3 C4 1.505(17) . ? C4 C5 1.514(18) . ? C5 C6 1.557(18) . ? C7 C8 1.524(17) . ? C8 C9 1.529(16) . ? C9 C10 1.489(18) . ? C10 C15 1.365(19) . ? C10 C11 1.41(2) . ? C11 C12 1.37(2) . ? C12 C13 1.38(2) . ? C13 C14 1.39(2) . ? C14 C15 1.390(18) . ? C16 C17 1.489(17) . ? C17 C18 1.511(17) . ? C18 C19 1.493(18) . ? C19 C20 1.38(2) . ? C19 C24 1.392(19) . ? C20 C21 1.36(2) . ? C21 C22 1.37(2) . ? C22 C23 1.38(2) . ? C23 C24 1.36(2) . ? C25 C26 1.522(16) . ? C26 C27 1.516(16) . ? C27 C28 1.466(18) . ? C28 C33 1.365(17) . ? C28 C29 1.401(19) . ? C29 C30 1.338(19) . ? C30 C31 1.37(2) . ? C31 C32 1.34(2) . ? C32 C33 1.37(2) . ? 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 N3 Cu N5 169.9(4) . . ? N3 Cu N6 83.6(4) . . ? N5 Cu N6 93.3(4) . . ? N3 Cu N1 89.6(4) . . ? N5 Cu N1 95.0(4) . . ? N6 Cu N1 168.0(4) . . ? N3 Cu N2 91.7(4) . . ? N5 Cu N2 79.3(4) . . ? N6 Cu N2 99.8(4) . . ? N1 Cu N2 90.2(4) . . ? N3 Cu N4 98.4(4) . . ? N5 Cu N4 91.3(4) . . ? N6 Cu N4 91.4(3) . . ? N1 Cu N4 79.8(4) . . ? N2 Cu N4 165.7(4) . . ? O3 Cl1 O1 110.0(9) . . ? O3 Cl1 O4 113.2(8) . . ? O1 Cl1 O4 111.4(8) . . ? O3 Cl1 O2 105.4(9) . . ? O1 Cl1 O2 106.2(10) . . ? O4 Cl1 O2 110.3(8) . . ? O6 Cl2 O7 107.9(7) . . ? O6 Cl2 O5 109.8(7) . . ? O7 Cl2 O5 109.5(8) . . ? O6 Cl2 O8 113.0(6) . . ? O7 Cl2 O8 108.0(7) . . ? O5 Cl2 O8 108.7(7) . . ? C7 N1 C1 113.3(10) . . ? C7 N1 Cu 110.0(8) . . ? C1 N1 Cu 116.6(8) . . ? C16 N2 C3 117.7(11) . . ? C16 N2 Cu 106.6(8) . . ? C3 N2 Cu 111.4(8) . . ? C25 N3 C5 112.2(10) . . ? C25 N3 Cu 109.1(7) . . ? C5 N3 Cu 115.6(8) . . ? C8 N4 Cu 107.0(7) . . ? C17 N5 Cu 112.6(7) . . ? C26 N6 Cu 107.3(7) . . ? C2 C1 N1 110.0(11) . . ? C2 C1 C6 109.0(12) . . ? N1 C1 C6 112.1(11) . . ? C1 C2 C3 118.3(12) . . ? N2 C3 C4 109.4(11) . . ? N2 C3 C2 111.3(11) . . ? C4 C3 C2 110.8(12) . . ? C3 C4 C5 115.1(12) . . ? N3 C5 C4 115.0(11) . . ? N3 C5 C6 108.8(11) . . ? C4 C5 C6 110.1(12) . . ? C1 C6 C5 112.9(11) . . ? N1 C7 C8 115.0(11) . . ? N4 C8 C7 107.0(11) . . ? N4 C8 C9 115.4(11) . . ? C7 C8 C9 108.2(12) . . ? C10 C9 C8 113.0(12) . . ? C15 C10 C11 116.0(15) . . ? C15 C10 C9 125.2(15) . . ? C11 C10 C9 118.8(17) . . ? C12 C11 C10 122.1(17) . . ? C11 C12 C13 120.4(18) . . ? C12 C13 C14 119.1(16) . . ? C13 C14 C15 119.3(16) . . ? C10 C15 C14 123.2(15) . . ? N2 C16 C17 112.2(12) . . ? N5 C17 C16 106.8(11) . . ? N5 C17 C18 110.3(11) . . ? C16 C17 C18 115.7(12) . . ? C19 C18 C17 116.0(12) . . ? C20 C19 C24 116.1(15) . . ? C20 C19 C18 123.9(16) . . ? C24 C19 C18 120.0(16) . . ? C21 C20 C19 121.9(17) . . ? C20 C21 C22 122(2) . . ? C21 C22 C23 117.2(18) . . ? C24 C23 C22 121.1(16) . . ? C23 C24 C19 121.7(15) . . ? N3 C25 C26 108.6(10) . . ? N6 C26 C27 113.5(11) . . ? N6 C26 C25 106.7(10) . . ? C27 C26 C25 111.5(11) . . ? C28 C27 C26 114.6(12) . . ? C33 C28 C29 115.8(15) . . ? C33 C28 C27 123.4(16) . . ? C29 C28 C27 120.7(14) . . ? C30 C29 C28 121.8(15) . . ? C29 C30 C31 120.9(19) . . ? C32 C31 C30 118.9(18) . . ? C31 C32 C33 120.6(16) . . ? C28 C33 C32 121.9(16) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 C2 C3 C4 -47.7(17) . . . . ? C2 C3 C4 C5 47.2(16) . . . . ? C3 C4 C5 C6 -52.1(16) . . . . ? C4 C5 C6 C1 54.9(15) . . . . ? C5 C6 C1 C2 -53.2(15) . . . . ? C6 C1 C2 C3 50.5(16) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 19.93 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.284 _refine_diff_density_min -0.270 _refine_diff_density_rms 0.066 data_rp27 _database_code_depnum_ccdc_archive 'CCDC 221225' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural RP27 _chemical_formula_analytical ? _chemical_formula_sum 'C33 H49 Cl2 N6 O4.50 Zn' _chemical_formula_weight 738.05 _chemical_melting_point ? _chemical_compound_source ? 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 14.260(2) _cell_length_b 14.790(2) _cell_length_c 17.453(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3681.1(8) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1200 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description parallelepiped _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.332 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1556 _exptl_absorpt_coefficient_mu 0.857 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min 0.73 _exptl_absorpt_correction_T_max 0.97 _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16847 _diffrn_reflns_av_R_equivalents 0.2302 _diffrn_reflns_av_sigmaI/netI 0.2530 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 23.25 _reflns_number_total 5293 _reflns_number_observed 2500 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 834 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0638P)^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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0036(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.04(3) _refine_ls_number_reflns 5293 _refine_ls_number_parameters 443 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2101 _refine_ls_R_factor_gt 0.0840 _refine_ls_wR_factor_ref 0.1648 _refine_ls_wR_factor_gt 0.1328 _refine_ls_goodness_of_fit_ref 0.912 _refine_ls_restrained_S_all 0.912 _refine_ls_shift/su_max 0.027 _refine_ls_shift/su_mean 0.006 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Zn Zn 0.55323(9) 0.15804(9) 0.08602(7) 0.0335(4) Uani 1 1 d . Cl1 Cl 0.5956(3) -0.1168(4) 0.2540(3) 0.0923(15) Uani 1 1 d . Cl2 Cl 0.78786(19) 0.3327(2) 0.02859(16) 0.0446(9) Uani 1 1 d . O1 O 0.5818(13) -0.0342(12) 0.2968(10) 0.214(9) Uani 1 1 d . O2 O 0.6386(9) -0.0875(9) 0.1893(7) 0.149(6) Uani 1 1 d . O3 O 0.6427(7) -0.1743(8) 0.3011(6) 0.115(4) Uani 1 1 d . O4 O 0.5024(8) -0.1529(11) 0.2397(7) 0.162(6) Uani 1 1 d . O5 O 0.4535(15) 0.1596(17) 0.3325(11) 0.125(8) Uani 0.50 1 d P N1 N 0.6983(6) 0.1332(5) 0.0500(5) 0.029(2) Uani 1 1 d . H1 H 0.7225 0.1900 0.0386 0.034 Uiso 1 1 calc R N2 N 0.5180(6) 0.1903(6) -0.0326(5) 0.034(3) Uani 1 1 d . H2 H 0.4535 0.1828 -0.0372 0.041 Uiso 1 1 calc R N3 N 0.5298(6) 0.0135(6) 0.0614(5) 0.040(3) Uani 1 1 d . H3 H 0.5644 -0.0181 0.0978 0.048 Uiso 1 1 calc R N4 N 0.6218(6) 0.1478(7) 0.1978(4) 0.040(3) Uani 1 1 d . H4A H 0.6008 0.1932 0.2295 0.048 Uiso 1 1 calc R H4B H 0.6076 0.0932 0.2202 0.048 Uiso 1 1 calc R N5 N 0.5615(6) 0.3033(5) 0.0905(5) 0.032(2) Uani 1 1 d . H5A H 0.5344 0.3237 0.1351 0.038 Uiso 1 1 calc R H5B H 0.6233 0.3210 0.0902 0.038 Uiso 1 1 calc R N6 N 0.4138(6) 0.1413(6) 0.1313(4) 0.041(3) Uani 1 1 d . H6A H 0.4080 0.1732 0.1764 0.049 Uiso 1 1 calc R H6B H 0.3706 0.1636 0.0970 0.049 Uiso 1 1 calc R C1 C 0.7115(9) 0.0793(9) -0.0202(6) 0.045(4) Uani 1 1 d . H1A H 0.7805 0.0739 -0.0292 0.053 Uiso 1 1 calc R C2 C 0.6696(7) 0.1293(7) -0.0888(6) 0.034(3) Uani 1 1 d . H2A H 0.6923 0.1926 -0.0878 0.040 Uiso 1 1 calc R H2B H 0.6936 0.1010 -0.1363 0.040 Uiso 1 1 calc R C3 C 0.5622(8) 0.1305(6) -0.0923(6) 0.029(3) Uani 1 1 d . H3A H 0.5433 0.1535 -0.1439 0.035 Uiso 1 1 calc R C4 C 0.5241(8) 0.0345(7) -0.0836(6) 0.038(3) Uani 1 1 d . H4B' H 0.5376 0.0005 -0.1312 0.045 Uiso 1 1 calc R H4C H 0.4552 0.0377 -0.0777 0.045 Uiso 1 1 calc R C5 C 0.5648(8) -0.0180(8) -0.0155(6) 0.039(3) Uani 1 1 d . H5B' H 0.5457 -0.0827 -0.0215 0.047 Uiso 1 1 calc R C6 C 0.6724(7) -0.0151(9) -0.0154(6) 0.041(4) Uani 1 1 d . H6B' H 0.6957 -0.0441 0.0320 0.049 Uiso 1 1 calc R H6C H 0.6959 -0.0506 -0.0595 0.049 Uiso 1 1 calc R C7 C 0.7520(8) 0.1018(8) 0.1175(6) 0.037(3) Uani 1 1 d . H7A H 0.8200 0.1076 0.1072 0.045 Uiso 1 1 calc R H7B H 0.7382 0.0372 0.1271 0.045 Uiso 1 1 calc R C8 C 0.7271(7) 0.1559(9) 0.1866(6) 0.036(3) Uani 1 1 d . H8A H 0.7426 0.2207 0.1763 0.044 Uiso 1 1 calc R C9 C 0.7830(8) 0.1247(8) 0.2560(6) 0.045(4) Uani 1 1 d . H9A H 0.7580 0.0652 0.2723 0.054 Uiso 1 1 calc R H9B H 0.8487 0.1152 0.2397 0.054 Uiso 1 1 calc R C10 C 0.7835(10) 0.1866(8) 0.3252(6) 0.040(4) Uani 1 1 d . C11 C 0.8629(11) 0.2360(12) 0.3413(8) 0.075(5) Uani 1 1 d . H11A H 0.9165 0.2324 0.3092 0.090 Uiso 1 1 calc R C12 C 0.8626(13) 0.2914(10) 0.4059(10) 0.082(5) Uani 1 1 d . H12A H 0.9175 0.3244 0.4189 0.099 Uiso 1 1 calc R C13 C 0.7860(14) 0.2987(10) 0.4501(9) 0.080(5) Uani 1 1 d . H13A H 0.7864 0.3382 0.4929 0.096 Uiso 1 1 calc R C14 C 0.7064(12) 0.2490(12) 0.4336(8) 0.079(5) Uani 1 1 d . H14A H 0.6521 0.2539 0.4649 0.094 Uiso 1 1 calc R C15 C 0.7071(11) 0.1924(10) 0.3712(8) 0.061(4) Uani 1 1 d . H15A H 0.6533 0.1569 0.3601 0.073 Uiso 1 1 calc R C16 C 0.5373(8) 0.2886(8) -0.0458(6) 0.043(3) Uani 1 1 d . H16A H 0.6047 0.2971 -0.0574 0.051 Uiso 1 1 calc R H16B H 0.5007 0.3098 -0.0905 0.051 Uiso 1 1 calc R C17 C 0.5118(7) 0.3435(8) 0.0229(6) 0.033(3) Uani 1 1 d . H17A H 0.4426 0.3391 0.0314 0.040 Uiso 1 1 calc R C18 C 0.5392(8) 0.4452(7) 0.0140(6) 0.037(3) Uani 1 1 d . H18A H 0.5229 0.4770 0.0621 0.045 Uiso 1 1 calc R H18B H 0.6081 0.4489 0.0079 0.045 Uiso 1 1 calc R C19 C 0.4952(8) 0.4943(8) -0.0503(7) 0.030(3) Uani 1 1 d . C20 C 0.4198(9) 0.5531(8) -0.0398(7) 0.039(3) Uani 1 1 d . H20A H 0.3947 0.5621 0.0100 0.047 Uiso 1 1 calc R C21 C 0.3810(8) 0.5988(7) -0.1027(7) 0.041(3) Uani 1 1 d . H21A H 0.3312 0.6405 -0.0950 0.049 Uiso 1 1 calc R C22 C 0.4144(10) 0.5839(10) -0.1747(7) 0.054(4) Uani 1 1 d . H22A H 0.3847 0.6122 -0.2171 0.065 Uiso 1 1 calc R C23 C 0.4899(11) 0.5287(9) -0.1872(8) 0.057(4) Uani 1 1 d . H23A H 0.5147 0.5208 -0.2373 0.068 Uiso 1 1 calc R C24 C 0.5289(8) 0.4854(8) -0.1257(7) 0.044(3) Uani 1 1 d . H24A H 0.5815 0.4474 -0.1344 0.052 Uiso 1 1 calc R C25 C 0.4320(8) -0.0078(7) 0.0766(6) 0.038(3) Uani 1 1 d . H25A H 0.4256 -0.0736 0.0855 0.045 Uiso 1 1 calc R H25B H 0.3938 0.0081 0.0311 0.045 Uiso 1 1 calc R C26 C 0.3951(9) 0.0431(8) 0.1458(6) 0.038(3) Uani 1 1 d . H26A H 0.4318 0.0239 0.1918 0.046 Uiso 1 1 calc R C27 C 0.2917(8) 0.0204(8) 0.1594(6) 0.037(3) Uani 1 1 d . H27A H 0.2547 0.0436 0.1156 0.045 Uiso 1 1 calc R H27B H 0.2846 -0.0461 0.1603 0.045 Uiso 1 1 calc R C28 C 0.2514(8) 0.0581(9) 0.2316(7) 0.031(3) Uani 1 1 d . C29 C 0.2078(9) 0.1392(10) 0.2296(7) 0.054(4) Uani 1 1 d . H29A H 0.2044 0.1727 0.1832 0.065 Uiso 1 1 calc R C30 C 0.1681(10) 0.1726(9) 0.2959(9) 0.067(4) Uani 1 1 d . H30A H 0.1378 0.2298 0.2948 0.081 Uiso 1 1 calc R C31 C 0.1717(10) 0.1251(11) 0.3633(8) 0.059(4) Uani 1 1 d . H31A H 0.1420 0.1479 0.4080 0.071 Uiso 1 1 calc R C32 C 0.2178(11) 0.0455(12) 0.3652(8) 0.069(5) Uani 1 1 d . H32A H 0.2230 0.0131 0.4120 0.083 Uiso 1 1 calc R C33 C 0.2576(8) 0.0111(9) 0.2988(8) 0.046(4) Uani 1 1 d . H33A H 0.2893 -0.0454 0.3001 0.055 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 Zn 0.0284(8) 0.0414(8) 0.0306(7) -0.0007(8) 0.0009(7) -0.0017(8) Cl1 0.064(3) 0.109(4) 0.105(4) 0.055(3) 0.006(3) 0.003(3) Cl2 0.0268(18) 0.049(2) 0.058(2) -0.001(2) 0.0043(15) -0.0099(19) O1 0.24(2) 0.179(17) 0.222(17) 0.031(15) 0.096(16) 0.031(16) O2 0.121(12) 0.212(15) 0.114(9) 0.106(10) 0.041(9) -0.016(10) O3 0.096(9) 0.104(10) 0.144(10) 0.069(8) -0.065(8) -0.005(8) O4 0.076(8) 0.298(19) 0.112(10) 0.083(13) -0.008(7) -0.087(12) O5 0.094(17) 0.129(18) 0.152(19) 0.049(18) -0.065(15) -0.037(19) N1 0.026(6) 0.019(6) 0.040(6) 0.003(5) -0.001(5) -0.010(4) N2 0.028(6) 0.045(7) 0.028(6) -0.003(5) 0.006(5) -0.006(5) N3 0.018(6) 0.056(7) 0.045(7) -0.009(5) -0.001(5) -0.009(5) N4 0.045(7) 0.045(7) 0.030(5) -0.002(6) 0.005(5) 0.002(6) N5 0.029(5) 0.032(5) 0.035(5) 0.002(5) -0.004(6) 0.002(5) N6 0.041(7) 0.053(8) 0.029(5) 0.000(6) 0.001(4) 0.008(6) C1 0.039(8) 0.064(10) 0.030(8) -0.023(7) 0.004(6) -0.011(8) C2 0.035(7) 0.042(8) 0.024(6) 0.008(7) 0.012(6) -0.002(6) C3 0.045(7) 0.033(7) 0.010(5) 0.002(5) -0.005(6) -0.001(6) C4 0.043(8) 0.034(7) 0.036(7) 0.001(7) 0.010(7) -0.004(6) C5 0.038(8) 0.036(8) 0.043(8) -0.030(6) -0.011(7) 0.007(7) C6 0.021(7) 0.051(10) 0.050(9) -0.008(7) 0.013(6) 0.018(7) C7 0.030(8) 0.046(8) 0.036(8) -0.010(7) 0.007(6) 0.003(7) C8 0.029(8) 0.041(8) 0.039(8) -0.004(8) -0.006(6) -0.005(8) C9 0.045(9) 0.058(10) 0.032(8) -0.001(7) 0.001(7) 0.003(7) C10 0.045(9) 0.049(10) 0.027(8) 0.017(7) 0.006(7) 0.022(8) C11 0.054(11) 0.118(15) 0.052(10) -0.001(10) -0.015(8) -0.039(11) C12 0.096(14) 0.081(12) 0.069(12) -0.001(11) -0.008(11) -0.041(11) C13 0.099(15) 0.071(13) 0.070(12) -0.013(9) -0.023(12) -0.015(12) C14 0.085(14) 0.100(14) 0.051(11) 0.012(10) 0.001(9) 0.021(12) C15 0.075(12) 0.071(12) 0.036(9) 0.011(8) -0.012(9) 0.000(9) C16 0.029(8) 0.072(10) 0.026(7) 0.015(7) -0.002(6) -0.012(7) C17 0.030(7) 0.033(8) 0.036(7) 0.014(7) 0.009(5) 0.022(7) C18 0.027(8) 0.048(9) 0.038(7) -0.003(6) -0.009(7) 0.004(7) C19 0.024(7) 0.041(9) 0.024(7) -0.003(7) 0.003(6) -0.017(7) C20 0.045(9) 0.033(8) 0.039(8) -0.003(7) 0.013(7) -0.004(7) C21 0.043(8) 0.019(7) 0.061(10) 0.001(7) -0.015(8) 0.009(6) C22 0.073(12) 0.062(11) 0.027(8) 0.024(8) -0.020(8) -0.014(9) C23 0.064(11) 0.055(10) 0.052(10) 0.002(9) 0.000(8) 0.017(9) C24 0.033(9) 0.045(9) 0.053(9) -0.002(8) -0.010(7) 0.004(7) C25 0.045(9) 0.031(7) 0.037(7) -0.002(6) -0.002(7) -0.015(7) C26 0.053(9) 0.036(9) 0.026(7) 0.001(6) 0.005(6) -0.012(7) C27 0.017(7) 0.047(9) 0.048(8) 0.000(7) 0.014(6) -0.008(7) C28 0.023(7) 0.036(9) 0.033(8) -0.003(7) 0.002(6) -0.007(6) C29 0.055(10) 0.058(12) 0.049(10) -0.017(9) -0.012(8) -0.027(9) C30 0.093(13) 0.029(10) 0.080(11) -0.004(9) -0.030(10) 0.004(9) C31 0.071(11) 0.063(12) 0.043(9) -0.013(9) 0.021(8) -0.014(9) C32 0.068(12) 0.082(13) 0.057(11) 0.025(10) 0.016(9) 0.006(11) C33 0.027(8) 0.057(10) 0.054(9) 0.011(9) 0.008(7) 0.012(7) _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 Zn N5 2.152(7) . ? Zn N6 2.154(8) . ? Zn N4 2.187(8) . ? Zn N2 2.183(8) . ? Zn N1 2.192(8) . ? Zn N3 2.205(9) . ? Cl1 O2 1.357(10) . ? Cl1 O3 1.360(9) . ? Cl1 O1 1.445(17) . ? Cl1 O4 1.454(11) . ? N1 C1 1.475(12) . ? N1 C7 1.481(12) . ? N2 C16 1.497(12) . ? N2 C3 1.506(11) . ? N3 C25 1.454(12) . ? N3 C5 1.507(12) . ? N4 C8 1.520(12) . ? N5 C17 1.498(11) . ? N6 C26 1.498(13) . ? C1 C6 1.505(15) . ? C1 C2 1.529(14) . ? C2 C3 1.532(13) . ? C3 C4 1.527(13) . ? C4 C5 1.534(13) . ? C5 C6 1.534(14) . ? C7 C8 1.490(13) . ? C8 C9 1.523(13) . ? C9 C10 1.515(14) . ? C10 C15 1.357(16) . ? C10 C11 1.376(16) . ? C11 C12 1.394(18) . ? C12 C13 1.342(19) . ? C13 C14 1.383(18) . ? C14 C15 1.373(17) . ? C16 C17 1.494(13) . ? C17 C18 1.562(14) . ? C18 C19 1.476(14) . ? C19 C20 1.394(14) . ? C19 C24 1.407(14) . ? C20 C21 1.403(14) . ? C21 C22 1.362(15) . ? C22 C23 1.368(16) . ? C23 C24 1.368(15) . ? C25 C26 1.517(13) . ? C26 C27 1.531(14) . ? C27 C28 1.492(14) . ? C28 C29 1.352(15) . ? C28 C33 1.367(15) . ? C29 C30 1.379(16) . ? C30 C31 1.371(16) . ? C31 C32 1.348(17) . ? C32 C33 1.387(16) . ? 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 N5 Zn N6 98.7(3) . . ? N5 Zn N4 90.7(3) . . ? N6 Zn N4 94.4(3) . . ? N5 Zn N2 80.1(3) . . ? N6 Zn N2 99.3(3) . . ? N4 Zn N2 164.5(3) . . ? N5 Zn N1 97.2(3) . . ? N6 Zn N1 163.1(3) . . ? N4 Zn N1 79.8(3) . . ? N2 Zn N1 89.0(3) . . ? N5 Zn N3 169.2(3) . . ? N6 Zn N3 79.6(3) . . ? N4 Zn N3 100.0(4) . . ? N2 Zn N3 89.6(3) . . ? N1 Zn N3 85.7(3) . . ? O2 Cl1 O3 118.7(9) . . ? O2 Cl1 O1 102.9(9) . . ? O3 Cl1 O1 106.5(10) . . ? O2 Cl1 O4 112.8(8) . . ? O3 Cl1 O4 109.0(8) . . ? O1 Cl1 O4 105.9(10) . . ? C1 N1 C7 115.2(8) . . ? C1 N1 Zn 116.7(7) . . ? C7 N1 Zn 108.3(6) . . ? C16 N2 C3 112.8(8) . . ? C16 N2 Zn 108.4(6) . . ? C3 N2 Zn 115.6(6) . . ? C25 N3 C5 114.3(9) . . ? C25 N3 Zn 108.7(6) . . ? C5 N3 Zn 115.1(7) . . ? C8 N4 Zn 108.7(6) . . ? C17 N5 Zn 110.0(6) . . ? C26 N6 Zn 109.7(6) . . ? N1 C1 C6 114.1(10) . . ? N1 C1 C2 109.8(10) . . ? C6 C1 C2 110.3(9) . . ? C3 C2 C1 115.3(9) . . ? N2 C3 C4 109.2(9) . . ? N2 C3 C2 113.4(8) . . ? C4 C3 C2 109.9(8) . . ? C3 C4 C5 114.4(9) . . ? N3 C5 C6 108.8(9) . . ? N3 C5 C4 114.1(9) . . ? C6 C5 C4 111.3(10) . . ? C1 C6 C5 113.4(10) . . ? N1 C7 C8 110.6(9) . . ? C7 C8 C9 110.9(10) . . ? C7 C8 N4 107.3(9) . . ? C9 C8 N4 113.0(9) . . ? C10 C9 C8 117.0(10) . . ? C15 C10 C11 120.4(13) . . ? C15 C10 C9 120.4(13) . . ? C11 C10 C9 119.2(13) . . ? C10 C11 C12 118.4(14) . . ? C13 C12 C11 120.9(15) . . ? C12 C13 C14 120.4(16) . . ? C15 C14 C13 118.9(15) . . ? C10 C15 C14 120.9(15) . . ? C17 C16 N2 111.1(9) . . ? C16 C17 N5 107.5(8) . . ? C16 C17 C18 112.5(9) . . ? N5 C17 C18 110.1(9) . . ? C19 C18 C17 116.3(9) . . ? C20 C19 C24 116.4(11) . . ? C20 C19 C18 122.3(11) . . ? C24 C19 C18 121.3(12) . . ? C19 C20 C21 120.1(11) . . ? C22 C21 C20 120.4(12) . . ? C21 C22 C23 121.2(12) . . ? C24 C23 C22 118.3(13) . . ? C23 C24 C19 123.4(12) . . ? N3 C25 C26 111.6(9) . . ? N6 C26 C25 106.6(8) . . ? N6 C26 C27 114.2(10) . . ? C25 C26 C27 110.4(9) . . ? C28 C27 C26 114.9(9) . . ? C29 C28 C33 120.2(12) . . ? C29 C28 C27 119.1(12) . . ? C33 C28 C27 120.7(12) . . ? C28 C29 C30 119.0(13) . . ? C31 C30 C29 121.4(14) . . ? C32 C31 C30 119.1(13) . . ? C31 C32 C33 120.0(14) . . ? C28 C33 C32 120.2(13) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 C2 C3 C4 -51.0(12) . . . . ? C2 C3 C4 C5 49.5(12) . . . . ? C3 C4 C5 C6 -51.1(12) . . . . ? C4 C5 C6 C1 52.8(12) . . . . ? C5 C6 C1 C2 -53.3(13) . . . . ? C6 C1 C2 C3 53.4(12) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 23.25 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.417 _refine_diff_density_min -0.370 _refine_diff_density_rms 0.087