# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_global data_1 #TrackingRef 'Cu-Pzc.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H6 Cl2 Cu2 N4 O4 ' _chemical_formula_sum 'C10 H6 Cl2 Cu2 N4 O4' _chemical_formula_weight 444.17 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' Cu Cu 0.3201 1.2651 '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 'Pc ' _symmetry_space_group_name_Hall 'P -2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' _cell_length_a 7.044 _cell_length_b 10.511 _cell_length_c 9.693 _cell_angle_alpha 90.00 _cell_angle_beta 106.24 _cell_angle_gamma 90.00 _cell_volume 689.0 _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 940 _cell_measurement_theta_min 3.58 _cell_measurement_theta_max 27.20 _exptl_crystal_description needle _exptl_crystal_colour blue _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.141 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 436 _exptl_absorpt_coefficient_mu 3.496 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5415 _exptl_absorpt_correction_T_max 0.6047 _exptl_absorpt_process_details 'Higashi, T. (1995)' _exptl_special_details ; Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 2916 _diffrn_reflns_av_R_equivalents 0.0655 _diffrn_reflns_av_sigmaI/netI 0.1201 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1769 _reflns_number_gt 1277 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.1524P)^2^+1.2501P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.62(7) _refine_ls_number_reflns 1769 _refine_ls_number_parameters 199 _refine_ls_number_restraints 44 _refine_ls_R_factor_all 0.1202 _refine_ls_R_factor_gt 0.0942 _refine_ls_wR_factor_ref 0.2602 _refine_ls_wR_factor_gt 0.2265 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.038 _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 Cu1 Cu 1.45320(13) 0.77943(10) 0.71251(12) 0.0359(3) Uani 1 1 d . . . Cu2 Cu 0.90538(13) 0.70717(10) 1.18200(11) 0.0331(3) Uani 1 1 d . . . N4 N 0.5892(10) 0.7436(7) 0.5544(9) 0.0333(17) Uani 1 1 d U . . N1 N 1.2936(10) 0.7845(6) 0.8510(8) 0.025(2) Uani 1 1 d . . . N2 N 1.0637(11) 0.7431(7) 1.0418(9) 0.035(2) Uani 1 1 d . . . N3 N 0.7495(10) 0.7083(6) 0.3277(9) 0.025(2) Uani 1 1 d . . . O3 O 1.1595(9) 0.8686(6) 0.5568(6) 0.0383(19) Uani 1 1 d . . . O1 O 1.3219(9) 0.6112(6) 0.6646(8) 0.0393(19) Uani 1 1 d . . . C2 C 1.1948(12) 0.6767(8) 0.8508(10) 0.031(2) Uani 1 1 d . . . Cl1 Cl 1.6239(4) 0.9550(3) 0.7931(4) 0.0648(8) Uani 1 1 d . . . O4 O 1.0897(9) 0.8059(6) 0.3250(7) 0.041(2) Uani 1 1 d . . . C4 C 1.1682(13) 0.8475(9) 1.0488(11) 0.038(2) Uani 1 1 d U . . H4 H 1.1652 0.9079 1.1182 0.045 Uiso 1 1 calc R . . C10 C 0.5752(11) 0.6597(8) 0.3276(12) 0.038(3) Uani 1 1 d . . . H10 H 0.5077 0.6088 0.2512 0.046 Uiso 1 1 calc R . . O2 O 1.1243(10) 0.4767(6) 0.7374(7) 0.045(2) Uani 1 1 d . . . C5 C 1.2824(14) 0.8706(9) 0.9566(11) 0.038(3) Uani 1 1 d . . . H5 H 1.3537 0.9461 0.9657 0.045 Uiso 1 1 calc R . . C9 C 0.4940(12) 0.6824(9) 0.4356(11) 0.037(3) Uani 1 1 d . . . H9 H 0.3660 0.6540 0.4264 0.045 Uiso 1 1 calc R . . C6 C 1.0516(13) 0.8219(8) 0.4441(12) 0.038(3) Uani 1 1 d . . . C8 C 0.7726(12) 0.7917(8) 0.5616(11) 0.0277(16) Uani 1 1 d U . . H8 H 0.8428 0.8365 0.6425 0.033 Uiso 1 1 calc R . . C3 C 1.0739(11) 0.6539(8) 0.9445(10) 0.028(2) Uani 1 1 d U . . H3 H 1.0033 0.5783 0.9384 0.033 Uiso 1 1 calc R . . C1 C 1.2072(13) 0.5771(9) 0.7388(11) 0.039(3) Uani 1 1 d . . . C7 C 0.8550(12) 0.7729(7) 0.4457(10) 0.0257(18) Uani 1 1 d U . . Cl2 Cl 0.6701(4) 0.6065(3) 1.0146(3) 0.0487(8) 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 Cu1 0.0421(6) 0.0429(6) 0.0293(6) -0.0109(5) 0.0206(5) -0.0091(5) Cu2 0.0425(6) 0.0400(5) 0.0215(5) -0.0032(5) 0.0165(5) -0.0042(5) N4 0.026(3) 0.038(3) 0.039(3) -0.002(3) 0.014(2) -0.010(2) N1 0.032(3) 0.026(3) 0.024(4) 0.004(3) 0.017(3) 0.003(3) N2 0.036(4) 0.032(4) 0.044(5) 0.008(4) 0.025(4) 0.001(3) N3 0.028(3) 0.025(4) 0.027(4) -0.002(3) 0.014(3) -0.002(3) O3 0.049(3) 0.050(4) 0.010(3) -0.008(3) -0.002(3) 0.001(3) O1 0.047(3) 0.040(3) 0.034(4) -0.001(3) 0.017(3) -0.010(3) C2 0.033(4) 0.046(5) 0.019(4) 0.018(4) 0.015(4) 0.016(4) Cl1 0.0738(14) 0.0689(15) 0.0659(16) -0.0399(14) 0.0429(12) -0.0375(13) O4 0.042(3) 0.062(4) 0.024(3) -0.014(3) 0.020(3) 0.002(3) C4 0.047(4) 0.044(4) 0.031(4) -0.006(3) 0.024(3) 0.004(3) C10 0.019(4) 0.036(5) 0.054(7) -0.020(5) 0.003(4) -0.015(4) O2 0.072(4) 0.039(3) 0.037(4) -0.021(3) 0.034(3) -0.021(3) C5 0.059(5) 0.029(4) 0.028(5) -0.007(4) 0.016(5) -0.009(4) C9 0.021(4) 0.049(5) 0.040(6) -0.027(5) 0.006(4) 0.011(4) C6 0.039(5) 0.026(4) 0.047(6) 0.019(4) 0.009(5) 0.003(4) C8 0.027(2) 0.034(3) 0.028(3) -0.001(2) 0.017(2) -0.003(2) C3 0.029(3) 0.037(4) 0.018(4) -0.003(3) 0.007(3) 0.008(3) C1 0.037(5) 0.045(5) 0.030(5) -0.010(5) 0.003(5) 0.001(4) C7 0.024(3) 0.031(3) 0.026(3) 0.004(3) 0.012(3) -0.004(3) Cl2 0.0445(12) 0.0669(15) 0.0347(13) -0.0172(13) 0.0112(11) -0.0126(13) _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 Cu1 N1 1.978(8) . ? Cu1 O1 1.989(6) . ? Cu1 N4 2.057(9) 1_655 ? Cu1 Cl1 2.222(3) . ? Cu1 O3 2.385(6) . ? Cu2 O4 1.918(6) 1_556 ? Cu2 N3 2.017(8) 1_556 ? Cu2 N2 2.020(9) . ? Cu2 Cl2 2.235(3) . ? Cu2 O2 2.436(6) 2_565 ? N4 C9 1.326(12) . ? N4 C8 1.370(11) . ? N4 Cu1 2.057(9) 1_455 ? N1 C2 1.330(11) . ? N1 C5 1.385(12) . ? N2 C4 1.313(12) . ? N2 C3 1.346(12) . ? N3 C10 1.330(11) . ? N3 C7 1.359(11) . ? N3 Cu2 2.017(8) 1_554 ? O3 C6 1.245(11) . ? O1 C1 1.274(13) . ? C2 C3 1.428(14) . ? C2 C1 1.529(14) . ? O4 C6 1.267(14) . ? O4 Cu2 1.918(6) 1_554 ? C4 C5 1.381(15) . ? C10 C9 1.347(16) . ? O2 C1 1.205(11) . ? O2 Cu2 2.436(6) 2_564 ? C6 C7 1.482(13) . ? C8 C7 1.415(14) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 O1 82.4(3) . . ? N1 Cu1 N4 169.2(3) . 1_655 ? O1 Cu1 N4 86.9(3) . 1_655 ? N1 Cu1 Cl1 95.4(2) . . ? O1 Cu1 Cl1 172.3(2) . . ? N4 Cu1 Cl1 95.4(2) 1_655 . ? N1 Cu1 O3 82.0(3) . . ? O1 Cu1 O3 86.4(2) . . ? N4 Cu1 O3 95.9(3) 1_655 . ? Cl1 Cu1 O3 100.63(17) . . ? O4 Cu2 N3 83.2(3) 1_556 1_556 ? O4 Cu2 N2 89.8(3) 1_556 . ? N3 Cu2 N2 168.8(3) 1_556 . ? O4 Cu2 Cl2 174.7(2) 1_556 . ? N3 Cu2 Cl2 94.2(2) 1_556 . ? N2 Cu2 Cl2 92.1(2) . . ? O4 Cu2 O2 90.6(2) 1_556 2_565 ? N3 Cu2 O2 106.6(3) 1_556 2_565 ? N2 Cu2 O2 82.1(3) . 2_565 ? Cl2 Cu2 O2 94.56(17) . 2_565 ? C9 N4 C8 117.6(9) . . ? C9 N4 Cu1 120.5(6) . 1_455 ? C8 N4 Cu1 121.6(6) . 1_455 ? C2 N1 C5 114.8(8) . . ? C2 N1 Cu1 111.9(6) . . ? C5 N1 Cu1 132.9(6) . . ? C4 N2 C3 118.6(9) . . ? C4 N2 Cu2 121.9(7) . . ? C3 N2 Cu2 119.3(6) . . ? C10 N3 C7 118.7(9) . . ? C10 N3 Cu2 132.9(7) . 1_554 ? C7 N3 Cu2 108.4(6) . 1_554 ? C6 O3 Cu1 127.6(6) . . ? C1 O1 Cu1 116.4(6) . . ? N1 C2 C3 123.2(9) . . ? N1 C2 C1 116.8(9) . . ? C3 C2 C1 119.9(8) . . ? C6 O4 Cu2 117.2(6) . 1_554 ? N2 C4 C5 122.3(9) . . ? N3 C10 C9 121.6(9) . . ? C1 O2 Cu2 166.5(6) . 2_564 ? C4 C5 N1 121.8(8) . . ? N4 C9 C10 122.6(8) . . ? O3 C6 O4 128.2(9) . . ? O3 C6 C7 118.1(10) . . ? O4 C6 C7 113.6(8) . . ? N4 C8 C7 119.9(8) . . ? N2 C3 C2 119.1(8) . . ? O2 C1 O1 128.5(10) . . ? O2 C1 C2 119.0(10) . . ? O1 C1 C2 112.3(8) . . ? N3 C7 C8 119.2(8) . . ? N3 C7 C6 117.2(9) . . ? C8 C7 C6 123.6(8) . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 1.302 _refine_diff_density_min -1.080 _refine_diff_density_rms 0.247 _database_code_depnum_ccdc_archive 'CCDC 908035' data_2a #TrackingRef 'Cu-Pzc.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H8 Cl Cu2 N4 O5' _chemical_formula_sum 'C10 H8 Cl Cu2 N4 O5' _chemical_formula_weight 426.73 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' Cu Cu 0.3201 1.2651 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/c ' _symmetry_space_group_name_Hall '-P 2ybc ' 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 11.545(7) _cell_length_b 7.765(5) _cell_length_c 14.669(9) _cell_angle_alpha 90.00 _cell_angle_beta 95.146(8) _cell_angle_gamma 90.00 _cell_volume 1309.7(14) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2662 _cell_measurement_theta_min 2.79 _cell_measurement_theta_max 27.66 _exptl_crystal_description Block _exptl_crystal_colour Dark-blue _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.164 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 844 _exptl_absorpt_coefficient_mu 3.481 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5015 _exptl_absorpt_correction_T_max 0.5891 _exptl_absorpt_process_details 'Higashi, T. (1995)' _exptl_special_details ; Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 6029 _diffrn_reflns_av_R_equivalents 0.1013 _diffrn_reflns_av_sigmaI/netI 0.0828 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2282 _reflns_number_gt 1724 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0100P)^2^+150.0000P] 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 2282 _refine_ls_number_parameters 199 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.1617 _refine_ls_R_factor_gt 0.1278 _refine_ls_wR_factor_ref 0.2857 _refine_ls_wR_factor_gt 0.2654 _refine_ls_goodness_of_fit_ref 0.984 _refine_ls_restrained_S_all 0.983 _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 Cu1 Cu 0.07410(9) 0.75464(15) 0.39796(8) 0.0192(3) Uani 1 1 d . . . Cu2 Cu 0.53977(11) 0.58769(18) 0.68967(9) 0.0304(3) Uani 1 1 d . . . O1W O -0.0192(7) 0.7482(9) 0.5292(5) 0.036(2) Uani 1 1 d . . . H1WA H -0.0554 0.8312 0.5516 0.054 Uiso 1 1 d R . . H1WB H -0.0019 0.6763 0.5720 0.054 Uiso 1 1 d R . . Cl1 Cl 0.4602(2) 0.7513(4) 0.80614(19) 0.0350(7) Uani 1 1 d . . . O1 O 0.1430(6) 0.9792(9) 0.4215(5) 0.0291(18) Uani 1 1 d U . . O2 O 0.3022(8) 1.1127(10) 0.4904(7) 0.054(3) Uani 1 1 d . . . O3 O -0.1403(7) 0.3919(9) 0.2908(6) 0.043(2) Uani 1 1 d . . . O4 O 0.0161(5) 0.5293(9) 0.3614(5) 0.032(2) Uani 1 1 d . . . N1 N 0.2242(7) 0.6744(11) 0.4623(5) 0.021(2) Uani 1 1 d . . . N2 N 0.4240(7) 0.6282(11) 0.5805(5) 0.024(2) Uani 1 1 d . . . N3 N -0.2926(7) 0.8776(11) 0.2337(5) 0.023(2) Uani 1 1 d . . . N4 N -0.0745(7) 0.8317(11) 0.3294(5) 0.021(2) Uani 1 1 d . . . C1 C 0.2457(9) 0.9840(14) 0.4670(8) 0.031(3) Uani 1 1 d . . . C2 C 0.2910(8) 0.8073(12) 0.4961(6) 0.020(2) Uani 1 1 d U . . C3 C 0.3884(8) 0.7806(13) 0.5539(6) 0.022(2) Uani 1 1 d . . . H3A H 0.4315 0.8758 0.5753 0.027 Uiso 1 1 calc R . . C5 C 0.2609(7) 0.5139(11) 0.4859(6) 0.015(2) Uani 1 1 d . . . H5A H 0.2190 0.4183 0.4633 0.018 Uiso 1 1 calc R . . C4 C 0.3621(7) 0.4926(12) 0.5442(6) 0.016(2) Uani 1 1 d . . . H4A H 0.3879 0.3816 0.5587 0.019 Uiso 1 1 calc R . . C6 C -0.0864(9) 0.5232(14) 0.3149(7) 0.029(3) Uani 1 1 d . . . C7 C -0.1400(8) 0.6970(13) 0.2960(7) 0.023(2) Uani 1 1 d . . . C8 C -0.2471(8) 0.7240(13) 0.2491(7) 0.024(3) Uani 1 1 d . . . H8A H -0.2896 0.6285 0.2272 0.029 Uiso 1 1 calc R . . C9 C -0.2272(8) 1.0141(14) 0.2655(7) 0.025(3) Uani 1 1 d . . . H9A H -0.2550 1.1253 0.2545 0.030 Uiso 1 1 calc R . . C10 C -0.1189(9) 0.9906(12) 0.3145(7) 0.023(3) Uani 1 1 d . . . H10A H -0.0769 1.0860 0.3371 0.028 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 Cu1 0.0178(5) 0.0151(5) 0.0229(5) 0.0009(5) -0.0073(4) 0.0018(5) Cu2 0.0239(6) 0.0347(7) 0.0300(7) -0.0031(6) -0.0119(5) 0.0018(6) O1W 0.051(4) 0.009(3) 0.050(4) 0.003(3) 0.017(4) 0.003(3) Cl1 0.0324(12) 0.0346(14) 0.0367(14) -0.0138(13) -0.0043(11) 0.0077(12) O1 0.027(3) 0.024(3) 0.032(3) -0.002(3) -0.016(3) 0.012(3) O2 0.054(5) 0.013(4) 0.089(6) -0.007(4) -0.033(5) -0.006(4) O3 0.040(4) 0.010(3) 0.073(6) 0.003(4) -0.020(4) -0.009(3) O4 0.014(3) 0.015(3) 0.065(5) 0.018(3) -0.012(3) -0.001(3) N1 0.025(4) 0.021(4) 0.016(4) 0.003(3) -0.004(3) 0.008(4) N2 0.026(4) 0.023(4) 0.023(4) -0.014(3) 0.001(3) -0.003(4) N3 0.026(4) 0.032(5) 0.010(4) -0.001(3) -0.002(3) -0.011(4) N4 0.025(4) 0.020(4) 0.018(4) 0.003(3) 0.001(3) 0.001(4) C1 0.023(5) 0.027(5) 0.038(6) -0.002(5) -0.014(4) 0.000(5) C2 0.026(4) 0.022(4) 0.010(4) -0.003(3) 0.000(3) -0.007(3) C3 0.016(4) 0.026(5) 0.023(5) -0.005(4) -0.007(4) -0.009(4) C5 0.013(4) 0.008(4) 0.023(5) -0.002(4) -0.005(4) 0.001(3) C4 0.013(4) 0.012(4) 0.022(5) -0.002(4) -0.002(3) 0.003(4) C6 0.028(5) 0.032(6) 0.026(5) 0.002(5) -0.008(4) -0.005(5) C7 0.017(4) 0.030(5) 0.024(5) -0.010(4) 0.008(4) -0.011(4) C8 0.022(4) 0.019(5) 0.030(5) -0.008(4) -0.009(4) 0.002(4) C9 0.024(5) 0.026(5) 0.023(5) -0.003(4) -0.010(4) -0.006(4) C10 0.028(5) 0.009(4) 0.031(5) 0.000(4) -0.006(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 Cu1 O4 1.932(7) . ? Cu1 O1 1.935(7) . ? Cu1 N1 1.997(8) . ? Cu1 N4 2.000(8) . ? Cu1 O1W 2.289(8) . ? Cu2 N3 2.002(8) 4_676 ? Cu2 N2 2.017(8) . ? Cu2 Cl1 2.378(3) . ? Cu2 Cl1 2.613(4) 2_646 ? O1W H1WA 0.8501 . ? O1W H1WB 0.8503 . ? Cl1 Cu2 2.613(4) 2_656 ? O1 C1 1.308(12) . ? O2 C1 1.226(13) . ? O3 C6 1.230(13) . ? O4 C6 1.313(12) . ? N1 C5 1.351(12) . ? N1 C2 1.356(12) . ? N2 C3 1.302(13) . ? N2 C4 1.354(12) . ? N3 C8 1.315(13) . ? N3 C9 1.360(13) . ? N3 Cu2 2.002(8) 4_475 ? N4 C10 1.346(12) . ? N4 C7 1.357(12) . ? C1 C2 1.516(14) . ? C2 C3 1.362(12) . ? C3 H3A 0.9300 . ? C5 C4 1.395(12) . ? C5 H5A 0.9300 . ? C4 H4A 0.9300 . ? C6 C7 1.500(15) . ? C7 C8 1.376(13) . ? C8 H8A 0.9300 . ? C9 C10 1.397(13) . ? C9 H9A 0.9300 . ? C10 H10A 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 O4 Cu1 O1 173.0(3) . . ? O4 Cu1 N1 96.5(3) . . ? O1 Cu1 N1 82.6(3) . . ? O4 Cu1 N4 82.6(3) . . ? O1 Cu1 N4 98.1(3) . . ? N1 Cu1 N4 178.0(3) . . ? O4 Cu1 O1W 92.0(3) . . ? O1 Cu1 O1W 95.0(3) . . ? N1 Cu1 O1W 92.8(3) . . ? N4 Cu1 O1W 89.0(3) . . ? N3 Cu2 N2 142.0(3) 4_676 . ? N3 Cu2 Cl1 96.9(2) 4_676 . ? N2 Cu2 Cl1 102.5(2) . . ? N3 Cu2 Cl1 97.4(3) 4_676 2_646 ? N2 Cu2 Cl1 100.0(2) . 2_646 ? Cl1 Cu2 Cl1 121.08(9) . 2_646 ? Cu1 O1W H1WA 126.3 . . ? Cu1 O1W H1WB 122.6 . . ? H1WA O1W H1WB 107.7 . . ? Cu2 Cl1 Cu2 123.49(12) . 2_656 ? C1 O1 Cu1 117.1(7) . . ? C6 O4 Cu1 116.8(6) . . ? C5 N1 C2 117.0(8) . . ? C5 N1 Cu1 130.4(6) . . ? C2 N1 Cu1 112.1(6) . . ? C3 N2 C4 116.6(8) . . ? C3 N2 Cu2 123.3(6) . . ? C4 N2 Cu2 118.6(6) . . ? C8 N3 C9 116.5(8) . . ? C8 N3 Cu2 122.5(7) . 4_475 ? C9 N3 Cu2 119.8(7) . 4_475 ? C10 N4 C7 117.1(8) . . ? C10 N4 Cu1 130.8(7) . . ? C7 N4 Cu1 112.1(6) . . ? O2 C1 O1 127.0(10) . . ? O2 C1 C2 119.8(9) . . ? O1 C1 C2 113.1(9) . . ? N1 C2 C3 121.5(9) . . ? N1 C2 C1 114.5(8) . . ? C3 C2 C1 123.9(9) . . ? N2 C3 C2 123.1(9) . . ? N2 C3 H3A 118.5 . . ? C2 C3 H3A 118.5 . . ? N1 C5 C4 119.5(8) . . ? N1 C5 H5A 120.2 . . ? C4 C5 H5A 120.2 . . ? N2 C4 C5 122.1(8) . . ? N2 C4 H4A 118.9 . . ? C5 C4 H4A 118.9 . . ? O3 C6 O4 126.1(10) . . ? O3 C6 C7 120.2(9) . . ? O4 C6 C7 113.7(9) . . ? N4 C7 C8 120.7(9) . . ? N4 C7 C6 114.8(8) . . ? C8 C7 C6 124.5(9) . . ? N3 C8 C7 123.5(9) . . ? N3 C8 H8A 118.3 . . ? C7 C8 H8A 118.3 . . ? N3 C9 C10 121.2(9) . . ? N3 C9 H9A 119.4 . . ? C10 C9 H9A 119.4 . . ? N4 C10 C9 120.9(9) . . ? N4 C10 H10A 119.5 . . ? C9 C10 H10A 119.5 . . ? 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 N3 Cu2 Cl1 Cu2 75.5(3) 4_676 . . 2_656 ? N2 Cu2 Cl1 Cu2 -71.5(3) . . . 2_656 ? Cl1 Cu2 Cl1 Cu2 178.55(15) 2_646 . . 2_656 ? N1 Cu1 O1 C1 -1.9(8) . . . . ? N4 Cu1 O1 C1 -179.9(8) . . . . ? O1W Cu1 O1 C1 90.4(8) . . . . ? N1 Cu1 O4 C6 179.9(8) . . . . ? N4 Cu1 O4 C6 -1.9(8) . . . . ? O1W Cu1 O4 C6 86.8(8) . . . . ? O4 Cu1 N1 C5 -10.5(9) . . . . ? O1 Cu1 N1 C5 176.6(9) . . . . ? O1W Cu1 N1 C5 81.9(8) . . . . ? O4 Cu1 N1 C2 178.5(6) . . . . ? O1 Cu1 N1 C2 5.6(6) . . . . ? O1W Cu1 N1 C2 -89.1(6) . . . . ? N3 Cu2 N2 C3 -68.6(10) 4_676 . . . ? Cl1 Cu2 N2 C3 50.3(8) . . . . ? Cl1 Cu2 N2 C3 175.5(7) 2_646 . . . ? N3 Cu2 N2 C4 125.5(7) 4_676 . . . ? Cl1 Cu2 N2 C4 -115.5(7) . . . . ? Cl1 Cu2 N2 C4 9.6(7) 2_646 . . . ? O4 Cu1 N4 C10 179.7(9) . . . . ? O1 Cu1 N4 C10 -7.3(9) . . . . ? O1W Cu1 N4 C10 87.5(9) . . . . ? O4 Cu1 N4 C7 1.9(7) . . . . ? O1 Cu1 N4 C7 174.8(6) . . . . ? O1W Cu1 N4 C7 -90.3(7) . . . . ? Cu1 O1 C1 O2 -178.2(10) . . . . ? Cu1 O1 C1 C2 -1.9(12) . . . . ? C5 N1 C2 C3 -2.3(13) . . . . ? Cu1 N1 C2 C3 170.0(7) . . . . ? C5 N1 C2 C1 179.7(8) . . . . ? Cu1 N1 C2 C1 -8.0(10) . . . . ? O2 C1 C2 N1 -176.7(10) . . . . ? O1 C1 C2 N1 6.7(13) . . . . ? O2 C1 C2 C3 5.3(16) . . . . ? O1 C1 C2 C3 -171.2(9) . . . . ? C4 N2 C3 C2 3.1(14) . . . . ? Cu2 N2 C3 C2 -163.0(7) . . . . ? N1 C2 C3 N2 0.0(15) . . . . ? C1 C2 C3 N2 177.8(9) . . . . ? C2 N1 C5 C4 1.4(13) . . . . ? Cu1 N1 C5 C4 -169.2(7) . . . . ? C3 N2 C4 C5 -4.0(13) . . . . ? Cu2 N2 C4 C5 162.8(7) . . . . ? N1 C5 C4 N2 1.8(14) . . . . ? Cu1 O4 C6 O3 -175.3(9) . . . . ? Cu1 O4 C6 C7 1.5(12) . . . . ? C10 N4 C7 C8 -0.1(14) . . . . ? Cu1 N4 C7 C8 178.0(8) . . . . ? C10 N4 C7 C6 -179.8(9) . . . . ? Cu1 N4 C7 C6 -1.6(10) . . . . ? O3 C6 C7 N4 177.2(10) . . . . ? O4 C6 C7 N4 0.2(13) . . . . ? O3 C6 C7 C8 -2.5(16) . . . . ? O4 C6 C7 C8 -179.5(10) . . . . ? C9 N3 C8 C7 1.0(14) . . . . ? Cu2 N3 C8 C7 -166.6(8) 4_475 . . . ? N4 C7 C8 N3 0.1(16) . . . . ? C6 C7 C8 N3 179.7(10) . . . . ? C8 N3 C9 C10 -1.9(14) . . . . ? Cu2 N3 C9 C10 166.0(8) 4_475 . . . ? C7 N4 C10 C9 -0.8(14) . . . . ? Cu1 N4 C10 C9 -178.6(7) . . . . ? N3 C9 C10 N4 1.9(15) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 6.260 _refine_diff_density_min -1.179 _refine_diff_density_rms 0.382 _database_code_depnum_ccdc_archive 'CCDC 908036' data_3 #TrackingRef 'Cu-Pzc.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H8 Cu3 I2 N4 O5, H2 O' _chemical_formula_sum 'C10 H10 Cu3 I2 N4 O6' _chemical_formula_weight 726.64 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'Pbcn ' _symmetry_space_group_name_HALL '-P 2n 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 7.6664(16) _cell_length_b 31.951(7) _cell_length_c 15.481(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3792.0(14) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3244 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 28.19 _exptl_crystal_description block _exptl_crystal_colour bROWN _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.546 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2712 _exptl_absorpt_coefficient_mu 6.623 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2412 _exptl_absorpt_correction_T_max 0.3509 _exptl_absorpt_process_details 'Higashi, T. (1995)' _exptl_special_details ; Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 16467 _diffrn_reflns_av_R_equivalents 0.0966 _diffrn_reflns_av_sigmaI/netI 0.0845 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -37 _diffrn_reflns_limit_k_max 33 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 24.99 _reflns_number_total 3320 _reflns_number_gt 2208 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0414P)^2^+128.7179P] 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 3320 _refine_ls_number_parameters 227 _refine_ls_number_restraints 60 _refine_ls_R_factor_all 0.1308 _refine_ls_R_factor_gt 0.0867 _refine_ls_wR_factor_ref 0.1696 _refine_ls_wR_factor_gt 0.1536 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.081 _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 I1 I 0.26219(14) 0.47671(3) 0.44965(7) 0.0306(3) Uani 1 1 d . . . I2 I 0.25562(15) 0.45223(4) 0.17904(7) 0.0328(3) Uani 1 1 d . . . Cu1 Cu 0.0856(3) 0.43826(6) 0.32572(14) 0.0300(5) Uani 1 1 d . . . Cu2 Cu -0.0781(3) 0.46589(6) 0.46948(15) 0.0305(6) Uani 1 1 d . . . Cu3 Cu 0.2509(3) 0.22911(6) 0.37368(15) 0.0334(5) Uani 1 1 d . . . O3 O 0.0223(15) 0.2070(4) 0.3988(9) 0.043(4) Uani 1 1 d . . . O1 O 0.4840(15) 0.2541(3) 0.3663(9) 0.039(3) Uani 1 1 d . . . O4 O -0.1110(16) 0.1511(4) 0.4538(10) 0.055(4) Uani 1 1 d . . . O2 O 0.6185(16) 0.3156(4) 0.3536(12) 0.068(5) Uani 1 1 d . . . N3 N 0.3295(17) 0.1724(4) 0.4118(10) 0.031(4) Uani 1 1 d . . . N1 N 0.1718(17) 0.2890(4) 0.3675(10) 0.027(3) Uani 1 1 d . . . C8 C 0.488(2) 0.1553(5) 0.4132(13) 0.036(5) Uani 1 1 d . . . H8A H 0.5829 0.1708 0.3938 0.043 Uiso 1 1 calc R . . C1 C 0.485(2) 0.2943(5) 0.3598(13) 0.035(5) Uani 1 1 d . . . C6 C 0.021(2) 0.1703(6) 0.4311(12) 0.032(4) Uani 1 1 d . . . N4 N 0.3785(16) 0.0914(4) 0.4681(9) 0.025(3) Uani 1 1 d . . . N2 N 0.1267(16) 0.3744(4) 0.3466(9) 0.025(3) Uani 1 1 d . . . C9 C 0.514(2) 0.1152(5) 0.4428(10) 0.025(4) Uani 1 1 d . . . H9A H 0.6263 0.1043 0.4452 0.030 Uiso 1 1 calc R . . O5 O 0.2457(18) 0.2188(4) 0.2314(9) 0.057(4) Uani 1 1 d . . . H5WB H 0.2711 0.2187 0.1780 0.085 Uiso 1 1 d R . . H5WA H 0.1490 0.2059 0.2372 0.085 Uiso 1 1 d R . . C2 C 0.3107(18) 0.3147(5) 0.3595(10) 0.018(3) Uani 1 1 d U . . C3 C 0.287(2) 0.3574(5) 0.3495(11) 0.027(4) Uani 1 1 d U . . H3A H 0.3843 0.3747 0.3446 0.033 Uiso 1 1 calc R . . C4 C -0.007(2) 0.3479(5) 0.3576(11) 0.031(4) Uani 1 1 d U . . H4A H -0.1199 0.3588 0.3588 0.037 Uiso 1 1 calc R . . C5 C 0.013(2) 0.3061(5) 0.3670(12) 0.030(4) Uani 1 1 d U . . H5A H -0.0847 0.2890 0.3731 0.036 Uiso 1 1 calc R . . C10 C 0.2199(19) 0.1089(5) 0.4670(10) 0.024(4) Uani 1 1 d U . . H10A H 0.1250 0.0942 0.4887 0.028 Uiso 1 1 calc R . . C7 C 0.1957(19) 0.1481(5) 0.4346(10) 0.021(4) Uani 1 1 d . . . O1W O 0.5000 0.071(2) 0.2500 0.36(4) Uani 1 2 d SDU . . H1WA H 0.3920 0.0710 0.2375 0.427 Uiso 0.50 1 d PRD . . H1WB H 0.5198 0.0449 0.2559 0.427 Uiso 0.50 1 d PRD . . O2W O 0.0000 0.088(2) 0.2500 0.40(4) Uani 1 2 d SDU . . H2WA H 0.0732 0.1081 0.2437 0.483 Uiso 0.50 1 d PRD . . H2WB H 0.0624 0.0663 0.2402 0.483 Uiso 0.50 1 d PRD . . 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 I1 0.0201(6) 0.0287(6) 0.0430(7) -0.0106(5) 0.0009(5) -0.0027(5) I2 0.0236(6) 0.0414(7) 0.0333(6) 0.0046(5) -0.0006(6) -0.0091(6) Cu1 0.0298(12) 0.0206(12) 0.0395(13) -0.0004(10) 0.0010(10) 0.0008(9) Cu2 0.0281(12) 0.0196(12) 0.0438(14) 0.0010(10) 0.0025(10) -0.0013(9) Cu3 0.0191(11) 0.0175(11) 0.0637(15) 0.0077(10) -0.0032(12) 0.0010(9) O3 0.025(7) 0.025(7) 0.080(11) 0.020(7) -0.001(7) -0.003(6) O1 0.019(6) 0.021(7) 0.077(10) 0.004(7) -0.003(7) -0.002(5) O4 0.024(7) 0.043(9) 0.099(12) 0.036(8) -0.004(8) 0.004(6) O2 0.018(7) 0.035(9) 0.150(16) 0.002(9) 0.008(9) -0.004(6) N3 0.020(7) 0.019(8) 0.053(10) 0.010(7) -0.006(7) 0.007(6) N1 0.023(7) 0.009(7) 0.050(10) 0.001(6) 0.003(7) -0.005(6) C8 0.017(9) 0.018(10) 0.073(15) 0.005(9) 0.007(9) -0.003(7) C1 0.021(10) 0.016(10) 0.067(14) 0.001(9) 0.008(9) 0.011(8) C6 0.019(9) 0.041(12) 0.036(11) 0.012(9) 0.010(8) -0.001(8) N4 0.014(7) 0.021(8) 0.040(9) -0.004(7) -0.008(6) -0.006(6) N2 0.019(7) 0.024(8) 0.032(8) -0.002(6) 0.002(6) 0.000(6) C9 0.011(8) 0.027(10) 0.037(10) 0.014(8) 0.004(7) -0.004(7) O5 0.052(9) 0.062(9) 0.056(9) 0.008(7) 0.009(8) -0.012(8) C2 0.006(6) 0.018(7) 0.029(7) 0.001(6) -0.006(6) 0.005(5) C3 0.016(7) 0.028(7) 0.038(7) -0.002(6) 0.004(6) 0.002(6) C4 0.025(8) 0.023(8) 0.044(9) -0.003(7) 0.009(7) 0.014(7) C5 0.009(7) 0.034(9) 0.046(9) -0.010(8) 0.012(7) 0.000(7) C10 0.010(6) 0.028(7) 0.032(7) 0.004(6) 0.001(6) -0.010(6) C7 0.014(8) 0.019(9) 0.031(10) -0.001(7) -0.004(7) 0.005(7) O1W 0.36(4) 0.36(4) 0.35(4) 0.000 0.001(10) 0.000 O2W 0.40(4) 0.41(4) 0.40(4) 0.000 -0.003(10) 0.000 _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 I1 Cu2 2.631(2) 5_566 ? I1 Cu2 2.649(2) . ? I1 Cu1 2.650(2) . ? I2 Cu1 2.655(2) 3 ? I2 Cu1 2.656(2) . ? I2 Cu2 2.707(3) 3 ? Cu1 N2 2.091(13) . ? Cu1 I2 2.655(2) 3 ? Cu1 Cu1 2.687(4) 3 ? Cu1 Cu2 2.703(3) . ? Cu2 N4 2.096(13) 4_456 ? Cu2 I1 2.631(2) 5_566 ? Cu2 Cu2 2.660(4) 5_566 ? Cu2 I2 2.707(3) 3 ? Cu3 O3 1.929(12) . ? Cu3 O1 1.961(11) . ? Cu3 N3 1.999(13) . ? Cu3 N1 2.010(13) . ? Cu3 O5 2.227(14) . ? O3 C6 1.274(19) . ? O1 C1 1.290(19) . ? O4 C6 1.233(19) . ? O2 C1 1.23(2) . ? N3 C8 1.33(2) . ? N3 C7 1.33(2) . ? N1 C5 1.33(2) . ? N1 C2 1.350(18) . ? C8 C9 1.38(2) . ? C8 H8A 0.9300 . ? C1 C2 1.49(2) . ? C6 C7 1.52(2) . ? N4 C10 1.339(19) . ? N4 C9 1.344(19) . ? N4 Cu2 2.096(13) 4_556 ? N2 C4 1.34(2) . ? N2 C3 1.345(19) . ? C9 H9A 0.9300 . ? O5 H5WB 0.8507 . ? O5 H5WA 0.8514 . ? C2 C3 1.38(2) . ? C3 H3A 0.9300 . ? C4 C5 1.35(2) . ? C4 H4A 0.9300 . ? C5 H5A 0.9300 . ? C10 C7 1.36(2) . ? C10 H10A 0.9300 . ? O1W H1WA 0.8505 . ? O1W H1WB 0.8501 . ? O2W H2WA 0.8522 . ? O2W H2WB 0.8630 . ? 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 Cu2 I1 Cu2 60.50(8) 5_566 . ? Cu2 I1 Cu1 113.18(8) 5_566 . ? Cu2 I1 Cu1 61.34(7) . . ? Cu1 I2 Cu1 60.79(9) 3 . ? Cu1 I2 Cu2 60.54(7) 3 3 ? Cu1 I2 Cu2 120.43(8) . 3 ? N2 Cu1 I1 105.3(4) . . ? N2 Cu1 I2 108.5(4) . 3 ? I1 Cu1 I2 116.45(8) . 3 ? N2 Cu1 I2 102.9(4) . . ? I1 Cu1 I2 106.88(8) . . ? I2 Cu1 I2 115.56(9) 3 . ? N2 Cu1 Cu1 102.1(4) . 3 ? I1 Cu1 Cu1 151.79(6) . 3 ? I2 Cu1 Cu1 59.62(8) 3 3 ? I2 Cu1 Cu1 59.59(8) . 3 ? N2 Cu1 Cu2 105.1(4) . . ? I1 Cu1 Cu2 59.32(7) . . ? I2 Cu1 Cu2 60.69(7) 3 . ? I2 Cu1 Cu2 151.26(10) . . ? Cu1 Cu1 Cu2 119.44(12) 3 . ? N4 Cu2 I1 107.7(3) 4_456 5_566 ? N4 Cu2 I1 108.9(3) 4_456 . ? I1 Cu2 I1 119.50(8) 5_566 . ? N4 Cu2 Cu2 128.5(4) 4_456 5_566 ? I1 Cu2 Cu2 60.09(8) 5_566 5_566 ? I1 Cu2 Cu2 59.41(8) . 5_566 ? N4 Cu2 Cu1 99.7(4) 4_456 . ? I1 Cu2 Cu1 150.28(10) 5_566 . ? I1 Cu2 Cu1 59.34(7) . . ? Cu2 Cu2 Cu1 110.55(12) 5_566 . ? N4 Cu2 I2 99.8(4) 4_456 3 ? I1 Cu2 I2 104.29(8) 5_566 3 ? I1 Cu2 I2 114.68(9) . 3 ? Cu2 Cu2 I2 131.30(13) 5_566 3 ? Cu1 Cu2 I2 58.77(7) . 3 ? O3 Cu3 O1 171.5(6) . . ? O3 Cu3 N3 83.2(5) . . ? O1 Cu3 N3 96.4(5) . . ? O3 Cu3 N1 94.9(5) . . ? O1 Cu3 N1 83.4(5) . . ? N3 Cu3 N1 165.5(6) . . ? O3 Cu3 O5 97.4(5) . . ? O1 Cu3 O5 91.1(5) . . ? N3 Cu3 O5 99.4(6) . . ? N1 Cu3 O5 95.1(6) . . ? C6 O3 Cu3 115.2(10) . . ? C1 O1 Cu3 114.4(10) . . ? C8 N3 C7 117.3(13) . . ? C8 N3 Cu3 130.6(12) . . ? C7 N3 Cu3 112.0(10) . . ? C5 N1 C2 118.1(13) . . ? C5 N1 Cu3 131.6(11) . . ? C2 N1 Cu3 110.3(10) . . ? N3 C8 C9 121.2(15) . . ? N3 C8 H8A 119.4 . . ? C9 C8 H8A 119.4 . . ? O2 C1 O1 123.9(15) . . ? O2 C1 C2 120.3(15) . . ? O1 C1 C2 115.8(14) . . ? O4 C6 O3 125.3(16) . . ? O4 C6 C7 118.7(15) . . ? O3 C6 C7 115.8(14) . . ? C10 N4 C9 117.4(13) . . ? C10 N4 Cu2 121.0(10) . 4_556 ? C9 N4 Cu2 120.4(10) . 4_556 ? C4 N2 C3 116.3(14) . . ? C4 N2 Cu1 121.3(10) . . ? C3 N2 Cu1 122.4(11) . . ? N4 C9 C8 120.8(15) . . ? N4 C9 H9A 119.6 . . ? C8 C9 H9A 119.6 . . ? Cu3 O5 H5WB 163.4 . . ? Cu3 O5 H5WA 89.1 . . ? H5WB O5 H5WA 107.5 . . ? N1 C2 C3 120.5(13) . . ? N1 C2 C1 116.1(13) . . ? C3 C2 C1 123.3(14) . . ? N2 C3 C2 121.2(14) . . ? N2 C3 H3A 119.4 . . ? C2 C3 H3A 119.4 . . ? N2 C4 C5 123.2(15) . . ? N2 C4 H4A 118.4 . . ? C5 C4 H4A 118.4 . . ? N1 C5 C4 120.6(15) . . ? N1 C5 H5A 119.7 . . ? C4 C5 H5A 119.7 . . ? N4 C10 C7 120.9(14) . . ? N4 C10 H10A 119.6 . . ? C7 C10 H10A 119.6 . . ? N3 C7 C10 121.9(13) . . ? N3 C7 C6 113.4(13) . . ? C10 C7 C6 124.3(14) . . ? H1WA O1W H1WB 101.7 . . ? H2WA O2W H2WB 102.6 . . ? 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 Cu2 I1 Cu1 N2 -131.2(4) 5_566 . . . ? Cu2 I1 Cu1 N2 -98.8(4) . . . . ? Cu2 I1 Cu1 I2 -10.99(12) 5_566 . . 3 ? Cu2 I1 Cu1 I2 21.40(8) . . . 3 ? Cu2 I1 Cu1 I2 119.91(9) 5_566 . . . ? Cu2 I1 Cu1 I2 152.30(10) . . . . ? Cu2 I1 Cu1 Cu1 63.5(3) 5_566 . . 3 ? Cu2 I1 Cu1 Cu1 95.9(3) . . . 3 ? Cu2 I1 Cu1 Cu2 -32.39(11) 5_566 . . . ? Cu1 I2 Cu1 N2 96.6(4) 3 . . . ? Cu2 I2 Cu1 N2 107.4(4) 3 . . . ? Cu1 I2 Cu1 I1 -152.84(6) 3 . . . ? Cu2 I2 Cu1 I1 -141.96(8) 3 . . . ? Cu1 I2 Cu1 I2 -21.44(11) 3 . . 3 ? Cu2 I2 Cu1 I2 -10.56(14) 3 . . 3 ? Cu2 I2 Cu1 Cu1 10.88(6) 3 . . 3 ? Cu1 I2 Cu1 Cu2 -96.6(2) 3 . . . ? Cu2 I2 Cu1 Cu2 -85.7(2) 3 . . . ? Cu2 I1 Cu2 N4 -124.2(4) 5_566 . . 4_456 ? Cu1 I1 Cu2 N4 90.2(4) . . . 4_456 ? Cu2 I1 Cu2 I1 0.0 5_566 . . 5_566 ? Cu1 I1 Cu2 I1 -145.55(12) . . . 5_566 ? Cu1 I1 Cu2 Cu2 -145.54(12) . . . 5_566 ? Cu2 I1 Cu2 Cu1 145.54(12) 5_566 . . . ? Cu2 I1 Cu2 I2 124.90(13) 5_566 . . 3 ? Cu1 I1 Cu2 I2 -20.65(8) . . . 3 ? N2 Cu1 Cu2 N4 -7.3(5) . . . 4_456 ? I1 Cu1 Cu2 N4 -106.3(4) . . . 4_456 ? I2 Cu1 Cu2 N4 95.7(4) 3 . . 4_456 ? I2 Cu1 Cu2 N4 -174.0(4) . . . 4_456 ? Cu1 Cu1 Cu2 N4 106.4(4) 3 . . 4_456 ? N2 Cu1 Cu2 I1 -164.3(4) . . . 5_566 ? I1 Cu1 Cu2 I1 96.67(19) . . . 5_566 ? I2 Cu1 Cu2 I1 -61.33(19) 3 . . 5_566 ? I2 Cu1 Cu2 I1 29.0(3) . . . 5_566 ? Cu1 Cu1 Cu2 I1 -50.7(2) 3 . . 5_566 ? N2 Cu1 Cu2 I1 99.0(4) . . . . ? I2 Cu1 Cu2 I1 -158.00(8) 3 . . . ? I2 Cu1 Cu2 I1 -67.7(2) . . . . ? Cu1 Cu1 Cu2 I1 -147.32(8) 3 . . . ? N2 Cu1 Cu2 Cu2 130.4(4) . . . 5_566 ? I1 Cu1 Cu2 Cu2 31.34(11) . . . 5_566 ? I2 Cu1 Cu2 Cu2 -126.66(13) 3 . . 5_566 ? I2 Cu1 Cu2 Cu2 -36.3(3) . . . 5_566 ? Cu1 Cu1 Cu2 Cu2 -115.98(12) 3 . . 5_566 ? N2 Cu1 Cu2 I2 -103.0(4) . . . 3 ? I1 Cu1 Cu2 I2 158.00(8) . . . 3 ? I2 Cu1 Cu2 I2 90.3(2) . . . 3 ? Cu1 Cu1 Cu2 I2 10.67(7) 3 . . 3 ? N3 Cu3 O3 C6 4.1(13) . . . . ? N1 Cu3 O3 C6 -161.5(13) . . . . ? O5 Cu3 O3 C6 102.7(13) . . . . ? N3 Cu3 O1 C1 -166.5(14) . . . . ? N1 Cu3 O1 C1 -1.1(13) . . . . ? O5 Cu3 O1 C1 94.0(14) . . . . ? O3 Cu3 N3 C8 176.0(18) . . . . ? O1 Cu3 N3 C8 -12.6(18) . . . . ? N1 Cu3 N3 C8 -101(3) . . . . ? O5 Cu3 N3 C8 79.6(18) . . . . ? O3 Cu3 N3 C7 0.1(12) . . . . ? O1 Cu3 N3 C7 171.6(12) . . . . ? N1 Cu3 N3 C7 83(3) . . . . ? O5 Cu3 N3 C7 -96.3(12) . . . . ? O3 Cu3 N1 C5 -9.5(18) . . . . ? O1 Cu3 N1 C5 178.9(17) . . . . ? N3 Cu3 N1 C5 -91(3) . . . . ? O5 Cu3 N1 C5 88.4(17) . . . . ? O3 Cu3 N1 C2 173.1(12) . . . . ? O1 Cu3 N1 C2 1.5(12) . . . . ? N3 Cu3 N1 C2 91(2) . . . . ? O5 Cu3 N1 C2 -89.0(12) . . . . ? C7 N3 C8 C9 -5(3) . . . . ? Cu3 N3 C8 C9 179.8(13) . . . . ? Cu3 O1 C1 O2 -179.3(18) . . . . ? Cu3 O1 C1 C2 0(2) . . . . ? Cu3 O3 C6 O4 178.0(16) . . . . ? Cu3 O3 C6 C7 -7(2) . . . . ? I1 Cu1 N2 C4 123.5(12) . . . . ? I2 Cu1 N2 C4 -1.8(14) 3 . . . ? I2 Cu1 N2 C4 -124.7(12) . . . . ? Cu1 Cu1 N2 C4 -63.5(13) 3 . . . ? Cu2 Cu1 N2 C4 61.8(13) . . . . ? I1 Cu1 N2 C3 -56.8(13) . . . . ? I2 Cu1 N2 C3 177.9(12) 3 . . . ? I2 Cu1 N2 C3 55.0(13) . . . . ? Cu1 Cu1 N2 C3 116.1(12) 3 . . . ? Cu2 Cu1 N2 C3 -118.5(12) . . . . ? C10 N4 C9 C8 -3(2) . . . . ? Cu2 N4 C9 C8 -170.6(13) 4_556 . . . ? N3 C8 C9 N4 3(3) . . . . ? C5 N1 C2 C3 -1(2) . . . . ? Cu3 N1 C2 C3 176.6(13) . . . . ? C5 N1 C2 C1 -179.5(15) . . . . ? Cu3 N1 C2 C1 -1.8(19) . . . . ? O2 C1 C2 N1 -179.3(18) . . . . ? O1 C1 C2 N1 1(3) . . . . ? O2 C1 C2 C3 2(3) . . . . ? O1 C1 C2 C3 -177.3(16) . . . . ? C4 N2 C3 C2 3(2) . . . . ? Cu1 N2 C3 C2 -177.0(12) . . . . ? N1 C2 C3 N2 -1(3) . . . . ? C1 C2 C3 N2 177.6(16) . . . . ? C3 N2 C4 C5 -3(3) . . . . ? Cu1 N2 C4 C5 176.6(14) . . . . ? C2 N1 C5 C4 1(3) . . . . ? Cu3 N1 C5 C4 -176.4(13) . . . . ? N2 C4 C5 N1 1(3) . . . . ? C9 N4 C10 C7 5(2) . . . . ? Cu2 N4 C10 C7 173.0(12) 4_556 . . . ? C8 N3 C7 C10 7(3) . . . . ? Cu3 N3 C7 C10 -176.4(13) . . . . ? C8 N3 C7 C6 179.9(16) . . . . ? Cu3 N3 C7 C6 -3.6(18) . . . . ? N4 C10 C7 N3 -8(3) . . . . ? N4 C10 C7 C6 -179.8(16) . . . . ? O4 C6 C7 N3 -177.5(17) . . . . ? O3 C6 C7 N3 7(2) . . . . ? O4 C6 C7 C10 -5(3) . . . . ? O3 C6 C7 C10 179.8(16) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.587 _refine_diff_density_min -1.153 _refine_diff_density_rms 0.247 _database_code_depnum_ccdc_archive 'CCDC 908037'