# Electronic Supplementary Material (ESI) for Dalton Transactions # 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_ops _database_code_depnum_ccdc_archive 'CCDC 910909' #TrackingRef 'web_deposit_cif_file_0_BiplabMondal_1355370655.CIF of complex 1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C28 H36 Cl3 Cu2 N8 O12, Cl O4' _chemical_formula_sum 'C28 H36 Cl4 Cu2 N8 O16' _exptl_crystal_recrystallization_method methanol _chemical_melting_point ? _exptl_crystal_description cube _exptl_crystal_colour blue _diffrn_ambient_temperature 296(2) _chemical_formula_weight 1009.55 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 'P n m a' _symmetry_int_tables_number 62 _chemical_absolute_configuration syn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 14.4349(13) _cell_length_b 26.361(3) _cell_length_c 10.5333(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4008.1(7) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9285 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 24.05 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.673 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2056 _exptl_absorpt_coefficient_mu 1.406 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.609 _exptl_absorpt_correction_T_max 0.755 _exptl_absorpt_process_details SADBAS _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type Synthesised _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 48043 _diffrn_reflns_av_R_equivalents 0.0539 _diffrn_reflns_av_sigmaI/netI 0.0398 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.54 _diffrn_reflns_theta_max 27.67 _reflns_number_total 4618 _reflns_number_gt 3059 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SMART' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+12.1488P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4618 _refine_ls_number_parameters 275 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0913 _refine_ls_R_factor_gt 0.0543 _refine_ls_wR_factor_ref 0.1001 _refine_ls_wR_factor_gt 0.0920 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _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 Cl1 Cl 0.79505(11) 0.7500 0.91398(17) 0.0510(4) Uani 1 2 d S . . Cu1 Cu 0.24499(4) 0.615001(19) 0.54233(5) 0.04417(15) Uani 1 1 d . . . Cl2 Cl 0.18537(8) 0.48316(4) 0.55973(10) 0.0466(3) Uani 1 1 d . . . O3 O 0.6968(3) 0.7500 0.9168(5) 0.0708(15) Uani 1 2 d S . . O1 O 0.8316(2) 0.70538(12) 0.9684(4) 0.0849(12) Uani 1 1 d . . . O4 O 0.1529(3) 0.53073(13) 0.5159(5) 0.1061(15) Uani 1 1 d . . . O2 O 0.8252(5) 0.7500 0.7830(6) 0.111(2) Uani 1 2 d S . . O7 O 0.2170(3) 0.48857(14) 0.6857(3) 0.0925(13) Uani 1 1 d . . . O6 O 0.1131(3) 0.44773(15) 0.5554(4) 0.1047(15) Uani 1 1 d . . . O5 O 0.2571(3) 0.4696(2) 0.4806(5) 0.136(2) Uani 1 1 d . . . C10 C 0.4275(3) 0.58270(14) 0.5082(4) 0.0418(10) Uani 1 1 d . . . C14 C 0.3843(3) 0.56375(15) 0.7142(4) 0.0458(10) Uani 1 1 d . . . H14 H 0.3396 0.5638 0.7777 0.055 Uiso 1 1 calc R . . C11 C 0.5153(3) 0.56301(15) 0.5297(5) 0.0523(12) Uani 1 1 d . . . H11 H 0.5594 0.5630 0.4652 0.063 Uiso 1 1 calc R . . C5 C 0.0830(3) 0.65131(16) 0.6577(5) 0.0540(12) Uani 1 1 d . . . C6 C 0.0589(3) 0.64112(17) 0.5213(5) 0.0648(15) Uani 1 1 d . . . H6A H 0.0358 0.6068 0.5121 0.078 Uiso 1 1 calc R . . H6B H 0.0111 0.6644 0.4934 0.078 Uiso 1 1 calc R . . C12 C 0.5363(3) 0.54366(16) 0.6469(5) 0.0557(12) Uani 1 1 d . . . H12 H 0.5952 0.5309 0.6635 0.067 Uiso 1 1 calc R . . C1 C 0.1981(4) 0.64741(17) 0.8087(5) 0.0590(12) Uani 1 1 d . . . H1 H 0.2579 0.6382 0.8319 0.071 Uiso 1 1 calc R . . C4 C 0.0245(3) 0.67434(17) 0.7429(6) 0.0690(15) Uani 1 1 d . . . H4 H -0.0349 0.6839 0.7181 0.083 Uiso 1 1 calc R . . C7 C 0.1477(4) 0.62788(18) 0.3144(5) 0.0697(15) Uani 1 1 d . . . H7A H 0.1112 0.6487 0.2574 0.084 Uiso 1 1 calc R . . H7B H 0.1238 0.5935 0.3115 0.084 Uiso 1 1 calc R . . C13 C 0.4694(3) 0.54326(15) 0.7394(5) 0.0540(12) Uani 1 1 d . . . H13 H 0.4818 0.5292 0.8186 0.065 Uiso 1 1 calc R . . C9 C 0.3972(3) 0.60304(17) 0.3818(4) 0.0525(11) Uani 1 1 d . . . H9A H 0.4150 0.6384 0.3739 0.063 Uiso 1 1 calc R . . H9B H 0.4267 0.5841 0.3139 0.063 Uiso 1 1 calc R . . C8 C 0.2471(4) 0.62869(17) 0.2757(4) 0.0653(14) Uani 1 1 d . . . H8A H 0.2548 0.6139 0.1921 0.078 Uiso 1 1 calc R . . H8B H 0.2705 0.6632 0.2741 0.078 Uiso 1 1 calc R . . C2 C 0.1421(4) 0.67076(19) 0.8979(5) 0.0720(15) Uani 1 1 d . . . H2 H 0.1641 0.6778 0.9790 0.086 Uiso 1 1 calc R . . C3 C 0.0537(4) 0.68318(19) 0.8638(7) 0.0793(18) Uani 1 1 d . . . H3 H 0.0136 0.6976 0.9229 0.095 Uiso 1 1 calc R . . N4 N 0.3633(2) 0.58380(12) 0.6003(3) 0.0398(8) Uani 1 1 d . . . N2 N 0.1422(3) 0.64786(13) 0.4446(4) 0.0527(10) Uani 1 1 d . . . H2A H 0.1889 0.6638 0.4760 0.063 Uiso 1 1 calc R . . N1 N 0.1699(2) 0.63772(12) 0.6913(4) 0.0474(9) Uani 1 1 d . . . N3 N 0.2970(3) 0.59815(15) 0.3729(4) 0.0504(10) Uani 1 1 d . . . Cl3 Cl 0.0138(3) 0.7500 0.2502(3) 0.1209(12) Uani 1 2 d S . . O9 O -0.0359(6) 0.70758(18) 0.2522(10) 0.278(6) Uani 1 1 d . . . O8 O 0.0811(6) 0.7500 0.3417(8) 0.163(4) Uani 1 2 d S . . O10 O 0.0451(11) 0.7500 0.1348(11) 0.315(10) Uani 1 2 d S . . H16 H 0.286(3) 0.5704(14) 0.364(3) 0.028(11) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0394(8) 0.0346(8) 0.0790(12) 0.000 0.0018(8) 0.000 Cu1 0.0393(3) 0.0436(3) 0.0497(3) 0.0030(2) -0.0044(3) 0.0045(2) Cl2 0.0509(6) 0.0404(6) 0.0485(6) 0.0035(5) 0.0024(5) 0.0007(5) O3 0.045(3) 0.045(3) 0.123(5) 0.000 0.008(3) 0.000 O1 0.064(2) 0.0482(19) 0.143(4) 0.020(2) -0.024(2) 0.0045(17) O4 0.093(3) 0.055(2) 0.170(4) 0.041(3) -0.029(3) 0.003(2) O2 0.122(5) 0.120(5) 0.090(5) 0.000 0.044(4) 0.000 O7 0.140(4) 0.084(3) 0.053(2) 0.0107(19) -0.021(2) -0.037(3) O6 0.111(3) 0.081(3) 0.122(3) 0.027(3) -0.035(3) -0.051(3) O5 0.095(3) 0.197(5) 0.117(4) -0.054(4) 0.035(3) 0.040(4) C10 0.042(2) 0.029(2) 0.055(3) -0.0051(18) 0.001(2) -0.0032(18) C14 0.042(2) 0.047(2) 0.048(3) 0.004(2) -0.004(2) -0.002(2) C11 0.042(3) 0.042(2) 0.073(3) -0.016(2) 0.005(2) 0.000(2) C5 0.042(3) 0.035(2) 0.085(4) 0.014(2) 0.006(3) -0.002(2) C6 0.038(3) 0.046(3) 0.111(4) 0.018(3) -0.011(3) -0.001(2) C12 0.043(3) 0.044(3) 0.081(4) -0.012(2) -0.011(3) 0.008(2) C1 0.058(3) 0.053(3) 0.066(3) 0.004(3) 0.007(3) 0.001(2) C4 0.046(3) 0.045(3) 0.117(5) 0.015(3) 0.020(3) 0.005(2) C7 0.087(4) 0.049(3) 0.073(3) -0.004(3) -0.041(3) 0.012(3) C13 0.058(3) 0.040(2) 0.064(3) -0.001(2) -0.018(3) 0.004(2) C9 0.061(3) 0.046(3) 0.050(3) -0.004(2) 0.008(2) -0.005(2) C8 0.105(4) 0.048(3) 0.043(3) 0.001(2) -0.012(3) 0.023(3) C2 0.080(4) 0.061(3) 0.074(4) 0.000(3) 0.030(3) 0.000(3) C3 0.079(4) 0.048(3) 0.111(5) 0.010(3) 0.049(4) 0.006(3) N4 0.0376(19) 0.0354(18) 0.0464(19) -0.0006(15) 0.0003(16) -0.0005(15) N2 0.049(2) 0.040(2) 0.069(3) 0.0023(19) -0.020(2) -0.0011(17) N1 0.038(2) 0.0374(19) 0.067(3) 0.0097(18) 0.0067(18) -0.0010(16) N3 0.067(3) 0.033(2) 0.052(2) 0.0001(18) -0.0118(19) 0.0045(19) Cl3 0.191(3) 0.0464(11) 0.125(2) 0.000 -0.103(2) 0.000 O9 0.322(10) 0.061(3) 0.451(13) 0.025(6) -0.294(10) -0.044(5) O8 0.239(9) 0.048(3) 0.202(8) 0.000 -0.174(7) 0.000 O10 0.286(17) 0.56(3) 0.105(8) 0.000 -0.024(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 Cl1 O1 1.411(3) 7_575 ? Cl1 O1 1.411(3) . ? Cl1 O3 1.418(4) . ? Cl1 O2 1.446(6) . ? Cu1 N3 1.987(4) . ? Cu1 N4 1.992(3) . ? Cu1 N1 1.998(4) . ? Cu1 N2 2.003(3) . ? Cl2 O5 1.377(4) . ? Cl2 O6 1.401(4) . ? Cl2 O7 1.410(3) . ? Cl2 O4 1.416(3) . ? C10 N4 1.342(5) . ? C10 C11 1.389(6) . ? C10 C9 1.500(6) . ? C14 N4 1.345(5) . ? C14 C13 1.368(6) . ? C11 C12 1.370(6) . ? C5 N1 1.352(5) . ? C5 C4 1.374(7) . ? C5 C6 1.502(7) . ? C6 N2 1.460(6) . ? C12 C13 1.373(6) . ? C1 N1 1.327(6) . ? C1 C2 1.385(6) . ? C4 C3 1.362(8) . ? C7 N2 1.471(6) . ? C7 C8 1.493(7) . ? C9 N3 1.456(6) . ? C8 N3 1.488(5) . ? C2 C3 1.366(8) . ? Cl3 O10 1.297(12) . ? Cl3 O9 1.329(6) 7_575 ? Cl3 O9 1.329(6) . ? Cl3 O8 1.369(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cl1 O1 112.9(3) 7_575 . ? O1 Cl1 O3 111.4(2) 7_575 . ? O1 Cl1 O3 111.4(2) . . ? O1 Cl1 O2 105.9(2) 7_575 . ? O1 Cl1 O2 105.9(2) . . ? O3 Cl1 O2 108.8(4) . . ? N3 Cu1 N4 81.90(15) . . ? N3 Cu1 N1 167.74(16) . . ? N4 Cu1 N1 110.36(14) . . ? N3 Cu1 N2 85.11(16) . . ? N4 Cu1 N2 166.28(15) . . ? N1 Cu1 N2 82.67(16) . . ? O5 Cl2 O6 111.6(3) . . ? O5 Cl2 O7 110.7(3) . . ? O6 Cl2 O7 109.8(2) . . ? O5 Cl2 O4 106.3(3) . . ? O6 Cl2 O4 109.5(2) . . ? O7 Cl2 O4 108.9(3) . . ? N4 C10 C11 121.4(4) . . ? N4 C10 C9 115.7(4) . . ? C11 C10 C9 122.9(4) . . ? N4 C14 C13 122.1(4) . . ? C12 C11 C10 119.2(4) . . ? N1 C5 C4 121.1(5) . . ? N1 C5 C6 114.7(4) . . ? C4 C5 C6 124.2(5) . . ? N2 C6 C5 108.5(4) . . ? C11 C12 C13 119.2(4) . . ? N1 C1 C2 122.6(5) . . ? C3 C4 C5 119.8(5) . . ? N2 C7 C8 107.5(4) . . ? C14 C13 C12 119.4(4) . . ? N3 C9 C10 108.3(4) . . ? N3 C8 C7 105.7(4) . . ? C3 C2 C1 118.3(6) . . ? C4 C3 C2 119.6(5) . . ? C10 N4 C14 118.7(4) . . ? C10 N4 Cu1 112.3(3) . . ? C14 N4 Cu1 129.0(3) . . ? C6 N2 C7 121.1(4) . . ? C6 N2 Cu1 105.8(3) . . ? C7 N2 Cu1 106.6(3) . . ? C1 N1 C5 118.5(4) . . ? C1 N1 Cu1 128.5(3) . . ? C5 N1 Cu1 112.2(3) . . ? C9 N3 C8 118.5(4) . . ? C9 N3 Cu1 107.3(3) . . ? C8 N3 Cu1 108.3(3) . . ? O10 Cl3 O9 101.7(6) . 7_575 ? O10 Cl3 O9 101.7(6) . . ? O9 Cl3 O9 114.7(8) 7_575 . ? O10 Cl3 O8 114.3(9) . . ? O9 Cl3 O8 111.8(4) 7_575 . ? O9 Cl3 O8 111.8(4) . . ? _diffrn_measured_fraction_theta_max 0.965 _diffrn_reflns_theta_full 27.67 _diffrn_measured_fraction_theta_full 0.965 _refine_diff_density_max 0.620 _refine_diff_density_min -0.488 _refine_diff_density_rms 0.081 _platon_squeeze_details ; The Platon SQUEEZE procedure was applied to remove the contribution from the smeared elctron density from the crystal structure. These are presumed to be due to the disordered water molecules. During the procedure the highest Q peak was 1.14 to 0.64. PLATON Reference : Spek, A.L. (2003), J.Appl.Cryst. 36, 7-13. ; data_2 _database_code_depnum_ccdc_archive 'CCDC 910910' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C30 H36 Cl3 Cu2 N8 O12, O' _chemical_formula_sum 'C30 H36 Cl3 Cu2 N8 O13' _chemical_compound_source Synthesised _exptl_crystal_recrystallization_method Acetonitrile _chemical_melting_point ? _exptl_crystal_description cube _exptl_crystal_colour blue _diffrn_ambient_temperature 296(2) _chemical_formula_weight 950.12 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 'P n m a' _symmetry_int_tables_number 62 _chemical_absolute_configuration ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 13.6944(4) _cell_length_b 26.3827(8) _cell_length_c 11.2946(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4080.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 8877 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 0.00 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.546 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1940 _exptl_absorpt_coefficient_mu 1.308 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.966 _exptl_absorpt_correction_T_max 0.977 _exptl_absorpt_process_details SADBAS _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 42599 _diffrn_reflns_av_R_equivalents 0.1019 _diffrn_reflns_av_sigmaI/netI 0.0381 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.54 _diffrn_reflns_theta_max 23.18 _reflns_number_total 2968 _reflns_number_gt 2197 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0200P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2968 _refine_ls_number_parameters 259 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.1461 _refine_ls_R_factor_gt 0.1303 _refine_ls_wR_factor_ref 0.3940 _refine_ls_wR_factor_gt 0.3822 _refine_ls_goodness_of_fit_ref 1.664 _refine_ls_restrained_S_all 1.673 _refine_ls_shift/su_max 0.035 _refine_ls_shift/su_mean 0.005 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 0.26087(9) 0.61615(5) 0.04737(11) 0.0560(7) Uani 1 1 d . . . Cl1 Cl 0.3240(2) 0.48039(12) 0.0482(3) 0.0729(11) Uani 1 1 d D . . Cl2 Cl 0.2097(4) 0.7500 0.0655(5) 0.0793(14) Uani 1 2 d SD . . N4 N 0.3194(6) 0.6389(3) 0.1986(7) 0.057(2) Uani 1 1 d . . . N1 N 0.1376(6) 0.5823(3) 0.0962(7) 0.053(2) Uani 1 1 d . . . N3 N 0.3900(8) 0.6381(6) -0.0172(9) 0.101(4) Uani 1 1 d . . . N2 N 0.1992(9) 0.6089(6) -0.1101(9) 0.118(5) Uani 1 1 d D . . C4 C -0.0231(7) 0.5619(5) 0.0372(10) 0.063(3) Uani 1 1 d . . . H4 H -0.0704 0.5628 -0.0219 0.076 Uiso 1 1 calc R . . C1 C 0.1206(8) 0.5581(4) 0.1981(9) 0.063(3) Uani 1 1 d . . . H1 H 0.1714 0.5554 0.2524 0.076 Uiso 1 1 calc R . . C6 C 0.0939(10) 0.6088(5) -0.1018(11) 0.075(3) Uani 1 1 d . . . H6A H 0.0658 0.5901 -0.1674 0.090 Uiso 1 1 calc R . . H6B H 0.0690 0.6432 -0.1037 0.090 Uiso 1 1 calc R . . C2 C 0.0327(8) 0.5371(4) 0.2268(11) 0.070(3) Uani 1 1 d . . . H2 H 0.0219 0.5212 0.2991 0.084 Uiso 1 1 calc R . . C11 C 0.4120(8) 0.6529(4) 0.1923(9) 0.057(3) Uani 1 1 d . . . C5 C 0.0677(8) 0.5832(4) 0.0165(9) 0.055(3) Uani 1 1 d . . . C3 C -0.0430(9) 0.5411(4) 0.1367(14) 0.079(4) Uani 1 1 d . . . H3 H -0.1053 0.5287 0.1514 0.094 Uiso 1 1 calc R . . C8 C 0.3467(11) 0.6288(5) -0.2265(12) 0.084(4) Uani 1 1 d . . . H8A H 0.3634 0.5974 -0.2665 0.101 Uiso 1 1 calc R . . H8B H 0.3631 0.6559 -0.2810 0.101 Uiso 1 1 calc R . . C10 C 0.4621(9) 0.6421(5) 0.0717(11) 0.075(3) Uani 1 1 d . . . H10A H 0.5070 0.6693 0.0525 0.090 Uiso 1 1 calc R . . H10B H 0.4989 0.6107 0.0764 0.090 Uiso 1 1 calc R . . C12 C 0.4618(10) 0.6758(4) 0.2843(13) 0.074(3) Uani 1 1 d . . . H12 H 0.5268 0.6852 0.2759 0.089 Uiso 1 1 calc R . . C15 C 0.2727(9) 0.6488(5) 0.3032(10) 0.067(3) Uani 1 1 d . . . H15 H 0.2072 0.6399 0.3103 0.081 Uiso 1 1 calc R . . C14 C 0.3189(12) 0.6719(5) 0.4005(10) 0.086(4) Uani 1 1 d . . . H14 H 0.2859 0.6784 0.4709 0.103 Uiso 1 1 calc R . . C9 C 0.4116(12) 0.6331(9) -0.1331(13) 0.131(7) Uani 1 1 d . . . H9A H 0.4535 0.6035 -0.1383 0.158 Uiso 1 1 calc R . . H9B H 0.4526 0.6620 -0.1523 0.158 Uiso 1 1 calc R . . C13 C 0.4139(14) 0.6841(5) 0.3861(15) 0.093(5) Uani 1 1 d . . . H13 H 0.4473 0.6988 0.4490 0.112 Uiso 1 1 calc R . . O1 O 0.265(2) 0.4761(8) 0.148(3) 0.35(2) Uani 1 1 d D . . O2 O 0.3439(10) 0.5292(5) 0.0775(14) 0.148(5) Uani 1 1 d D . . O3 O 0.4058(10) 0.4498(5) 0.0531(15) 0.172(6) Uani 1 1 d D . . O5 O 0.1624(8) 0.7045(4) 0.0532(11) 0.124(4) Uani 1 1 d D . . O8 O 0.6051(19) 0.7500 0.880(2) 0.220(14) Uani 1 2 d S . . C7 C 0.2428(11) 0.6291(9) -0.2170(14) 0.141(10) Uani 1 1 d D . . H7A H 0.2167 0.6102 -0.2836 0.170 Uiso 1 1 calc R . . H7B H 0.2209 0.6639 -0.2257 0.170 Uiso 1 1 calc R . . O6 O 0.3093(11) 0.7500 0.085(2) 0.155(8) Uani 1 2 d SD . . O4 O 0.316(3) 0.4987(15) -0.0684(17) 0.42(3) Uani 1 1 d D . . O7 O 0.202(2) 0.7500 0.1940(16) 0.205(11) Uani 1 2 d SD . . 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 0.0436(10) 0.0849(13) 0.0395(10) 0.0047(5) -0.0002(5) -0.0106(6) Cl1 0.0598(19) 0.073(2) 0.086(2) -0.0138(15) 0.0058(14) -0.0167(15) Cl2 0.080(3) 0.056(3) 0.103(4) 0.000 -0.007(3) 0.000 N4 0.051(6) 0.066(6) 0.054(5) 0.003(4) -0.004(4) 0.003(4) N1 0.043(5) 0.071(6) 0.046(5) 0.003(4) 0.003(4) 0.007(4) N3 0.057(7) 0.200(13) 0.045(6) -0.004(7) 0.002(5) -0.054(8) N2 0.068(8) 0.239(16) 0.048(6) 0.009(7) 0.001(5) -0.067(9) C4 0.033(6) 0.086(8) 0.070(8) -0.013(6) 0.003(5) -0.006(5) C1 0.058(7) 0.079(7) 0.054(6) 0.005(5) 0.009(5) 0.007(6) C6 0.076(9) 0.094(9) 0.053(7) 0.001(6) -0.013(6) -0.006(7) C2 0.061(7) 0.068(7) 0.080(8) 0.000(6) 0.038(6) 0.001(6) C11 0.059(7) 0.054(6) 0.058(6) 0.004(5) -0.005(5) 0.006(5) C5 0.050(6) 0.059(6) 0.055(6) -0.006(5) 0.006(5) -0.001(5) C3 0.048(7) 0.071(8) 0.117(11) -0.027(8) 0.019(7) -0.008(6) C8 0.093(11) 0.088(9) 0.072(9) -0.013(7) 0.022(8) -0.011(7) C10 0.052(7) 0.088(9) 0.085(8) 0.009(7) 0.003(6) -0.005(6) C12 0.076(8) 0.059(7) 0.087(9) -0.002(6) -0.033(7) -0.003(6) C15 0.066(7) 0.085(8) 0.052(7) 0.004(6) -0.005(6) 0.015(6) C14 0.108(12) 0.103(10) 0.046(7) -0.013(6) -0.006(7) 0.029(9) C9 0.070(10) 0.26(2) 0.066(9) -0.008(11) 0.022(8) -0.020(12) C13 0.127(13) 0.055(7) 0.097(12) -0.011(7) -0.055(10) 0.008(8) O1 0.50(4) 0.153(15) 0.39(3) 0.07(2) 0.34(3) 0.10(2) O2 0.115(10) 0.118(10) 0.211(14) -0.016(9) -0.019(9) 0.006(8) O3 0.123(11) 0.129(10) 0.263(18) 0.028(10) 0.049(10) 0.061(9) O5 0.091(8) 0.114(9) 0.166(12) 0.019(7) -0.015(6) -0.037(7) O8 0.28(3) 0.017(6) 0.36(3) 0.000 0.21(3) 0.000 C7 0.066(11) 0.30(3) 0.062(10) -0.016(13) 0.004(7) 0.018(12) O6 0.084(12) 0.102(12) 0.28(2) 0.000 -0.025(14) 0.000 O4 0.67(7) 0.45(6) 0.128(15) 0.09(2) -0.07(2) -0.27(6) O7 0.21(3) 0.22(3) 0.18(2) 0.000 -0.06(2) 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 Cu1 N2 1.978(10) . ? Cu1 N4 1.979(8) . ? Cu1 N1 1.988(8) . ? Cu1 N3 1.999(10) . ? Cl1 O2 1.356(12) . ? Cl1 O3 1.383(11) . ? Cl1 O1 1.393(14) . ? Cl1 O4 1.407(15) . ? Cl2 O5 1.371(10) 7_575 ? Cl2 O5 1.371(10) . ? Cl2 O6 1.381(14) . ? Cl2 O7 1.456(17) . ? N4 C11 1.323(14) . ? N4 C15 1.370(14) . ? N1 C5 1.315(13) . ? N1 C1 1.337(13) . ? N3 C9 1.349(17) . ? N3 C10 1.412(16) . ? N2 C6 1.446(18) . ? N2 C7 1.449(15) . ? C4 C3 1.279(17) . ? C4 C5 1.384(15) . ? C1 C2 1.364(14) . ? C6 C5 1.540(16) . ? C2 C3 1.457(17) . ? C11 C12 1.382(15) . ? C11 C10 1.552(16) . ? C8 C9 1.38(2) . ? C8 C7 1.428(19) . ? C12 C13 1.34(2) . ? C15 C14 1.407(18) . ? C14 C13 1.35(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 N2 Cu1 N4 167.9(5) . . ? N2 Cu1 N1 81.0(4) . . ? N4 Cu1 N1 103.9(3) . . ? N2 Cu1 N3 94.5(4) . . ? N4 Cu1 N3 82.4(4) . . ? N1 Cu1 N3 169.4(5) . . ? O2 Cl1 O3 112.4(10) . . ? O2 Cl1 O1 89.8(13) . . ? O3 Cl1 O1 112.8(14) . . ? O2 Cl1 O4 85.3(16) . . ? O3 Cl1 O4 108(2) . . ? O1 Cl1 O4 138(3) . . ? O5 Cl2 O5 122.1(11) 7_575 . ? O5 Cl2 O6 118.9(6) 7_575 . ? O5 Cl2 O6 118.9(6) . . ? O5 Cl2 O7 93.7(8) 7_575 . ? O5 Cl2 O7 93.7(8) . . ? O6 Cl2 O7 85.2(15) . . ? C11 N4 C15 116.1(9) . . ? C11 N4 Cu1 115.3(7) . . ? C15 N4 Cu1 127.8(8) . . ? C5 N1 C1 118.1(9) . . ? C5 N1 Cu1 114.9(7) . . ? C1 N1 Cu1 127.0(7) . . ? C9 N3 C10 123.0(12) . . ? C9 N3 Cu1 121.3(10) . . ? C10 N3 Cu1 112.4(8) . . ? C6 N2 C7 117.7(11) . . ? C6 N2 Cu1 111.6(8) . . ? C7 N2 Cu1 122.6(9) . . ? C3 C4 C5 120.8(11) . . ? N1 C1 C2 123.6(11) . . ? N2 C6 C5 106.8(10) . . ? C1 C2 C3 115.6(11) . . ? N4 C11 C12 123.7(11) . . ? N4 C11 C10 114.8(9) . . ? C12 C11 C10 121.5(11) . . ? N1 C5 C4 122.1(10) . . ? N1 C5 C6 115.6(9) . . ? C4 C5 C6 122.2(10) . . ? C4 C3 C2 119.6(11) . . ? C9 C8 C7 125.6(13) . . ? N3 C10 C11 109.2(9) . . ? C13 C12 C11 118.3(12) . . ? N4 C15 C14 123.1(12) . . ? C13 C14 C15 116.3(12) . . ? N3 C9 C8 127.4(14) . . ? C12 C13 C14 122.4(12) . . ? C8 C7 N2 118.1(14) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 23.18 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 2.224 _refine_diff_density_min -0.859 _refine_diff_density_rms 0.247 data_3 _database_code_depnum_ccdc_archive 'CCDC 910911' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H22 Cl2 Cu N5 O9' _chemical_compound_source Synthesised _exptl_crystal_recrystallization_method Acetonitrile _chemical_melting_point ? _exptl_crystal_description Cube _exptl_crystal_colour blue _diffrn_ambient_temperature 296(2) _chemical_formula_weight 610.88 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' 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' 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 'P n' _symmetry_int_tables_number 7 _chemical_absolute_configuration syn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y, z+1/2' _cell_length_a 8.7895(3) _cell_length_b 12.8229(5) _cell_length_c 11.1763(5) _cell_angle_alpha 90.00 _cell_angle_beta 94.308(2) _cell_angle_gamma 90.00 _cell_volume 1256.09(9) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 6907 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 0.00 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.615 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624.0 _exptl_absorpt_coefficient_mu 1.142 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.670 _exptl_absorpt_correction_T_max 0.787 _exptl_absorpt_process_details SADBAS _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16166 _diffrn_reflns_av_R_equivalents 0.0522 _diffrn_reflns_av_sigmaI/netI 0.0538 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.59 _diffrn_reflns_theta_max 28.58 _reflns_number_total 5401 _reflns_number_gt 3406 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0723P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.009(14) _refine_ls_number_reflns 5401 _refine_ls_number_parameters 334 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0719 _refine_ls_R_factor_gt 0.0454 _refine_ls_wR_factor_ref 0.1192 _refine_ls_wR_factor_gt 0.1098 _refine_ls_goodness_of_fit_ref 0.906 _refine_ls_restrained_S_all 0.906 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.08581(5) 0.70465(4) 0.69873(5) 0.05370(18) Uani 1 1 d . . . Cl1 Cl 0.53174(13) 0.53947(11) 0.69389(11) 0.0637(3) Uani 1 1 d . . . N1 N 0.0971(5) 0.5417(3) 0.6812(3) 0.0525(9) Uani 1 1 d . . . C5 C 0.1068(6) 0.4962(4) 0.7913(5) 0.0616(13) Uani 1 1 d . . . C2 C 0.0652(7) 0.3759(4) 0.5923(6) 0.0683(15) Uani 1 1 d . . . H2 H 0.0525 0.3364 0.5225 0.082 Uiso 1 1 calc R . . C1 C 0.0788(6) 0.4822(4) 0.5859(5) 0.0637(14) Uani 1 1 d . . . H1 H 0.0748 0.5135 0.5107 0.076 Uiso 1 1 calc R . . C3 C 0.0702(9) 0.3294(4) 0.6996(8) 0.0789(15) Uani 1 1 d . . . H3 H 0.0613 0.2573 0.7048 0.095 Uiso 1 1 calc R . . N2 N 0.0660(4) 0.6707(3) 0.8717(3) 0.0540(9) Uani 1 1 d . . . C13 C -0.0978(6) 0.6655(4) 0.8893(5) 0.0671(13) Uani 1 1 d . . . H13A H -0.1138 0.6771 0.9732 0.081 Uiso 1 1 calc R . . H13B H -0.1367 0.5968 0.8671 0.081 Uiso 1 1 calc R . . C6 C 0.1438(7) 0.5691(4) 0.8937(5) 0.0732(14) Uani 1 1 d . . . H6B H 0.1116 0.5385 0.9671 0.088 Uiso 1 1 calc R . . H6A H 0.2533 0.5799 0.9037 0.088 Uiso 1 1 calc R . . C16 C -0.0754(6) 0.7895(3) 0.4967(5) 0.0544(13) Uani 1 1 d . . . C20 C 0.1544(6) 0.7256(4) 0.4431(5) 0.0695(14) Uani 1 1 d . . . H20 H 0.2481 0.6941 0.4637 0.083 Uiso 1 1 calc R . . C15 C -0.1801(7) 0.8085(4) 0.5969(5) 0.0683(14) Uani 1 1 d . . . H15A H -0.1618 0.8771 0.6316 0.082 Uiso 1 1 calc R . . H15B H -0.2861 0.8043 0.5660 0.082 Uiso 1 1 calc R . . C14 C -0.1829(6) 0.7477(4) 0.8128(5) 0.0650(12) Uani 1 1 d . . . H14B H -0.2920 0.7424 0.8196 0.078 Uiso 1 1 calc R . . H14A H -0.1494 0.8172 0.8369 0.078 Uiso 1 1 calc R . . N4 N -0.1450(5) 0.7253(3) 0.6898(4) 0.0637(11) Uani 1 1 d . . . N5 N 0.0608(5) 0.7459(3) 0.5285(4) 0.0596(10) Uani 1 1 d . . . N3 N 0.2618(4) 0.7944(3) 0.7657(4) 0.0588(10) Uani 1 1 d . . . O1 O 0.4942(8) 0.6163(4) 0.6081(5) 0.140(2) Uani 1 1 d . . . O4 O 0.5022(6) 0.5781(5) 0.8042(4) 0.1151(16) Uani 1 1 d . . . C11 C 0.4724(7) 0.9092(5) 0.7588(8) 0.0879(18) Uani 1 1 d . . . H11 H 0.5399 0.9458 0.7142 0.105 Uiso 1 1 calc R . . C12 C 0.3622(6) 0.8474(4) 0.7036(5) 0.0691(14) Uani 1 1 d . . . H12 H 0.3562 0.8416 0.6204 0.083 Uiso 1 1 calc R . . C9 C 0.3829(6) 0.8636(4) 0.9466(6) 0.0757(15) Uani 1 1 d . . . H9 H 0.3891 0.8669 1.0300 0.091 Uiso 1 1 calc R . . O3 O 0.6882(5) 0.5157(4) 0.6910(5) 0.1077(16) Uani 1 1 d . . . O2 O 0.4479(5) 0.4492(4) 0.6630(5) 0.1152(16) Uani 1 1 d . . . C8 C 0.2721(6) 0.8042(4) 0.8848(6) 0.0590(14) Uani 1 1 d . . . O9 O 0.700(3) 0.9117(18) 0.1141(16) 0.52(2) Uani 1 1 d . . . C4 C 0.0890(7) 0.3897(5) 0.8042(6) 0.0747(17) Uani 1 1 d . . . H4 H 0.0895 0.3592 0.8797 0.090 Uiso 1 1 calc R . . C10 C 0.4817(7) 0.9164(5) 0.8832(8) 0.093(2) Uani 1 1 d . . . H10 H 0.5564 0.9579 0.9227 0.112 Uiso 1 1 calc R . . Cl2 Cl 0.94807(16) 0.04973(11) 0.86173(16) 0.0799(4) Uani 1 1 d . . . O5 O 0.8289(10) 0.0484(6) 0.7835(11) 0.249(6) Uani 1 1 d . . . O8 O 1.0637(9) -0.0005(6) 0.8171(10) 0.208(4) Uani 1 1 d . . . O6 O 0.904(2) -0.0068(7) 0.9474(10) 0.316(9) Uani 1 1 d . . . O7 O 0.9821(5) 0.1514(3) 0.9009(4) 0.0965(13) Uani 1 1 d . . . C17 C -0.1208(7) 0.8178(4) 0.3793(5) 0.0733(15) Uani 1 1 d . . . H17 H -0.2143 0.8495 0.3588 0.088 Uiso 1 1 calc R . . C7 C 0.1447(7) 0.7555(5) 0.9468(5) 0.0775(15) Uani 1 1 d . . . H7A H 0.0710 0.8088 0.9635 0.093 Uiso 1 1 calc R . . H7B H 0.1850 0.7263 1.0227 0.093 Uiso 1 1 calc R . . C18 C -0.0165(9) 0.7955(5) 0.2939(6) 0.0863(18) Uani 1 1 d . . . H18 H -0.0410 0.8130 0.2141 0.104 Uiso 1 1 calc R . . C19 C 0.1148(8) 0.7504(5) 0.3241(5) 0.0777(15) Uani 1 1 d . . . H19 H 0.1813 0.7350 0.2656 0.093 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0524(3) 0.0611(3) 0.0485(3) 0.0096(3) 0.0096(2) 0.0007(3) Cl1 0.0630(7) 0.0755(8) 0.0535(7) -0.0068(6) 0.0100(7) -0.0048(6) N1 0.066(2) 0.0505(19) 0.042(2) 0.0060(19) 0.0120(17) -0.002(2) C5 0.062(3) 0.061(3) 0.063(3) 0.003(3) 0.012(3) 0.009(2) C2 0.078(4) 0.056(3) 0.071(4) 0.001(3) 0.007(3) -0.003(3) C1 0.060(3) 0.066(3) 0.066(4) 0.006(3) 0.008(3) 0.004(2) C3 0.095(4) 0.058(3) 0.084(4) 0.000(4) 0.013(3) 0.007(4) N2 0.064(2) 0.053(2) 0.047(2) 0.0011(18) 0.0175(18) -0.0021(19) C13 0.063(3) 0.076(3) 0.063(3) 0.007(3) 0.014(2) 0.000(3) C6 0.082(4) 0.079(4) 0.060(3) 0.005(3) 0.012(3) 0.014(3) C16 0.053(3) 0.050(3) 0.060(3) 0.003(2) 0.004(2) 0.000(2) C20 0.067(3) 0.078(3) 0.064(4) 0.009(3) 0.014(3) -0.008(3) C15 0.071(3) 0.063(3) 0.070(4) 0.004(3) -0.002(3) 0.004(2) C14 0.050(3) 0.078(3) 0.069(3) 0.003(3) 0.020(2) 0.006(2) N4 0.053(2) 0.076(3) 0.064(3) 0.002(2) 0.013(2) 0.0072(19) N5 0.063(3) 0.067(3) 0.049(3) 0.010(2) 0.006(2) -0.002(2) N3 0.048(2) 0.055(2) 0.074(3) -0.002(2) 0.011(2) -0.0009(17) O1 0.206(6) 0.122(4) 0.097(4) 0.040(3) 0.036(4) 0.053(4) O4 0.110(4) 0.171(5) 0.067(3) -0.039(3) 0.025(2) -0.003(3) C11 0.077(4) 0.062(4) 0.127(6) 0.003(4) 0.020(4) -0.010(3) C12 0.069(3) 0.058(3) 0.081(4) -0.003(3) 0.014(3) -0.005(3) C9 0.061(3) 0.078(4) 0.087(4) -0.007(3) -0.007(3) 0.008(3) O3 0.061(3) 0.122(4) 0.142(4) -0.033(3) 0.016(2) -0.017(2) O2 0.089(3) 0.102(3) 0.155(5) -0.033(3) 0.018(3) -0.034(3) C8 0.049(3) 0.056(3) 0.072(4) 0.001(2) 0.010(3) 0.005(2) O9 0.60(4) 0.65(4) 0.300(18) 0.18(2) -0.12(2) -0.36(3) C4 0.099(4) 0.059(4) 0.068(4) 0.023(3) 0.016(3) 0.002(3) C10 0.060(3) 0.067(4) 0.149(7) -0.016(4) -0.014(4) -0.004(3) Cl2 0.0712(9) 0.0665(9) 0.1046(12) -0.0117(8) 0.0237(8) -0.0049(7) O5 0.169(7) 0.167(7) 0.392(15) -0.133(8) -0.111(9) 0.034(6) O8 0.142(6) 0.168(6) 0.324(13) -0.063(7) 0.095(7) 0.033(5) O6 0.69(3) 0.120(5) 0.155(7) -0.043(5) 0.134(11) -0.121(11) O7 0.092(3) 0.065(2) 0.132(4) -0.014(2) 0.009(3) -0.016(2) C17 0.081(4) 0.071(3) 0.066(4) 0.005(3) -0.010(3) -0.002(3) C7 0.077(4) 0.088(4) 0.066(4) -0.002(3) 0.000(3) -0.007(3) C18 0.104(5) 0.100(5) 0.055(4) 0.006(3) 0.007(4) -0.007(4) C19 0.081(4) 0.098(4) 0.056(3) 0.003(3) 0.014(3) -0.009(3) _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 N5 1.971(4) . ? Cu1 N2 2.002(4) . ? Cu1 N3 2.026(4) . ? Cu1 N4 2.041(4) . ? Cu1 N1 2.102(3) . ? Cl1 O4 1.371(4) . ? Cl1 O2 1.401(4) . ? Cl1 O1 1.397(5) . ? Cl1 O3 1.411(5) . ? N1 C1 1.310(7) . ? N1 C5 1.359(6) . ? C5 C4 1.383(8) . ? C5 C6 1.494(7) . ? C2 C3 1.337(10) . ? C2 C1 1.372(8) . ? C3 C4 1.402(10) . ? N2 C13 1.469(6) . ? N2 C6 1.483(6) . ? N2 C7 1.509(7) . ? C13 C14 1.518(8) . ? C16 N5 1.345(6) . ? C16 C17 1.390(8) . ? C16 C15 1.522(8) . ? C20 N5 1.331(7) . ? C20 C19 1.387(8) . ? C15 N4 1.504(7) . ? C14 N4 1.466(6) . ? N3 C8 1.333(7) . ? N3 C12 1.347(7) . ? C11 C12 1.363(8) . ? C11 C10 1.389(10) . ? C9 C10 1.345(9) . ? C9 C8 1.380(8) . ? C8 C7 1.496(8) . ? Cl2 O6 1.284(10) . ? Cl2 O5 1.313(7) . ? Cl2 O8 1.331(6) . ? Cl2 O7 1.400(4) . ? C17 C18 1.401(9) . ? C18 C19 1.312(9) . ? 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 Cu1 N2 168.26(18) . . ? N5 Cu1 N3 103.36(18) . . ? N2 Cu1 N3 83.46(17) . . ? N5 Cu1 N4 83.10(17) . . ? N2 Cu1 N4 85.26(16) . . ? N3 Cu1 N4 132.29(17) . . ? N5 Cu1 N1 100.32(17) . . ? N2 Cu1 N1 83.21(15) . . ? N3 Cu1 N1 124.00(16) . . ? N4 Cu1 N1 100.27(17) . . ? O4 Cl1 O2 112.9(3) . . ? O4 Cl1 O1 108.1(4) . . ? O2 Cl1 O1 108.7(4) . . ? O4 Cl1 O3 110.5(3) . . ? O2 Cl1 O3 108.1(3) . . ? O1 Cl1 O3 108.5(4) . . ? C1 N1 C5 118.8(4) . . ? C1 N1 Cu1 130.6(3) . . ? C5 N1 Cu1 110.0(3) . . ? N1 C5 C4 121.2(5) . . ? N1 C5 C6 114.9(5) . . ? C4 C5 C6 123.9(5) . . ? C3 C2 C1 119.5(6) . . ? N1 C1 C2 122.9(5) . . ? C2 C3 C4 119.7(5) . . ? C13 N2 C6 112.5(4) . . ? C13 N2 C7 111.8(4) . . ? C6 N2 C7 110.8(4) . . ? C13 N2 Cu1 107.2(3) . . ? C6 N2 Cu1 106.2(3) . . ? C7 N2 Cu1 108.1(3) . . ? N2 C13 C14 109.8(4) . . ? N2 C6 C5 110.6(4) . . ? N5 C16 C17 123.0(5) . . ? N5 C16 C15 116.6(5) . . ? C17 C16 C15 120.4(5) . . ? N5 C20 C19 121.2(6) . . ? N4 C15 C16 106.9(4) . . ? N4 C14 C13 104.8(4) . . ? C14 N4 C15 117.3(4) . . ? C14 N4 Cu1 105.9(3) . . ? C15 N4 Cu1 106.1(3) . . ? C20 N5 C16 118.5(5) . . ? C20 N5 Cu1 127.5(4) . . ? C16 N5 Cu1 113.5(4) . . ? C8 N3 C12 118.0(5) . . ? C8 N3 Cu1 114.5(3) . . ? C12 N3 Cu1 127.4(4) . . ? C12 C11 C10 118.6(6) . . ? N3 C12 C11 122.0(6) . . ? C10 C9 C8 118.3(6) . . ? N3 C8 C9 122.9(5) . . ? N3 C8 C7 115.2(5) . . ? C9 C8 C7 121.5(6) . . ? C5 C4 C3 117.7(5) . . ? C9 C10 C11 120.1(6) . . ? O6 Cl2 O5 102.7(9) . . ? O6 Cl2 O8 106.7(8) . . ? O5 Cl2 O8 109.7(7) . . ? O6 Cl2 O7 111.2(5) . . ? O5 Cl2 O7 111.2(4) . . ? O8 Cl2 O7 114.6(4) . . ? C16 C17 C18 115.7(6) . . ? C8 C7 N2 111.8(5) . . ? C19 C18 C17 121.5(6) . . ? C18 C19 C20 120.0(6) . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 28.58 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.442 _refine_diff_density_min -0.351 _refine_diff_density_rms 0.065 data_4 _database_code_depnum_ccdc_archive 'CCDC 910912' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H27 Cl2 Cu N7 O8' _chemical_compound_source Synthesised _exptl_crystal_recrystallization_method Acetonitrile _chemical_melting_point ? _exptl_crystal_description cube _exptl_crystal_colour blue _diffrn_ambient_temperature 293(2) _chemical_formula_weight 639.95 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 triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 _chemical_absolute_configuration syn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.9766(2) _cell_length_b 9.9809(2) _cell_length_c 16.3225(4) _cell_angle_alpha 91.1700(10) _cell_angle_beta 94.8440(10) _cell_angle_gamma 110.2890(10) _cell_volume 1364.84(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5210 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 0.00 _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.557 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 658.0 _exptl_absorpt_coefficient_mu 1.054 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.971 _exptl_absorpt_correction_T_max 0.982 _exptl_absorpt_process_details SADBAS _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12734 _diffrn_reflns_av_R_equivalents 0.0672 _diffrn_reflns_av_sigmaI/netI 0.0584 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.25 _diffrn_reflns_theta_max 28.43 _reflns_number_total 6639 _reflns_number_gt 3939 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1033P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6639 _refine_ls_number_parameters 354 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0747 _refine_ls_R_factor_gt 0.0549 _refine_ls_wR_factor_ref 0.1674 _refine_ls_wR_factor_gt 0.1550 _refine_ls_goodness_of_fit_ref 0.992 _refine_ls_restrained_S_all 0.992 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.83027(5) 0.37079(4) 0.25963(2) 0.04085(17) Uani 1 1 d . . . N1 N 0.9796(3) 0.5000(3) 0.34642(16) 0.0460(7) Uani 1 1 d . . . N2 N 0.7444(4) 0.5325(3) 0.24966(16) 0.0465(7) Uani 1 1 d . . . H22 H 0.8083 0.5927 0.2185 0.056 Uiso 1 1 d R . . N3 N 0.6385(3) 0.2567(3) 0.17832(16) 0.0411(6) Uani 1 1 d . . . N4 N 0.9533(3) 0.3769(3) 0.15250(17) 0.0470(7) Uani 1 1 d . . . N5 N 0.7913(3) 0.1789(3) 0.30398(17) 0.0455(7) Uani 1 1 d . . . N6 N 0.6090(4) -0.0275(3) 0.3240(2) 0.0590(9) Uani 1 1 d . . . C1 C 1.1150(5) 0.4874(4) 0.3819(2) 0.0577(10) Uani 1 1 d . . . H1 H 1.1417 0.4093 0.3660 0.069 Uiso 1 1 calc R . . C2 C 1.2139(5) 0.5840(4) 0.4400(3) 0.0639(11) Uani 1 1 d . . . H2 H 1.3058 0.5718 0.4639 0.077 Uiso 1 1 calc R . . C3 C 1.1756(5) 0.6994(5) 0.4625(3) 0.0674(12) Uani 1 1 d . . . H3 H 1.2422 0.7674 0.5018 0.081 Uiso 1 1 calc R . . C4 C 1.0381(6) 0.7155(4) 0.4272(2) 0.0679(12) Uani 1 1 d . . . H4 H 1.0111 0.7941 0.4420 0.081 Uiso 1 1 calc R . . C5 C 0.9412(4) 0.6122(4) 0.3692(2) 0.0493(9) Uani 1 1 d . . . C6 C 0.7854(5) 0.6174(4) 0.3291(2) 0.0574(10) Uani 1 1 d . . . H6A H 0.7015 0.5786 0.3649 0.069 Uiso 1 1 calc R . . H6B H 0.7955 0.7157 0.3198 0.069 Uiso 1 1 calc R . . C7 C 0.5728(4) 0.4656(4) 0.2209(2) 0.0506(9) Uani 1 1 d . . . H7A H 0.5300 0.5377 0.2019 0.061 Uiso 1 1 calc R . . H7B H 0.5135 0.4176 0.2653 0.061 Uiso 1 1 calc R . . C8 C 0.5598(4) 0.3592(4) 0.1510(2) 0.0502(9) Uani 1 1 d . . . H8B H 0.4483 0.3074 0.1331 0.060 Uiso 1 1 calc R . . H8A H 0.6102 0.4094 0.1048 0.060 Uiso 1 1 calc R . . C9 C 0.6971(4) 0.1964(4) 0.1101(2) 0.0469(8) Uani 1 1 d . . . H9A H 0.6238 0.1841 0.0610 0.056 Uiso 1 1 calc R . . H9B H 0.6987 0.1028 0.1238 0.056 Uiso 1 1 calc R . . C10 C 0.8594(4) 0.2882(3) 0.0922(2) 0.0434(8) Uani 1 1 d . . . C11 C 0.9143(5) 0.2715(4) 0.0157(3) 0.0625(11) Uani 1 1 d . . . H11 H 0.8457 0.2115 -0.0263 0.075 Uiso 1 1 calc R . . C12 C 1.0702(6) 0.3451(5) 0.0043(3) 0.0722(12) Uani 1 1 d . . . H12 H 1.1102 0.3337 -0.0451 0.087 Uiso 1 1 calc R . . C13 C 1.1662(5) 0.4353(5) 0.0662(3) 0.0646(11) Uani 1 1 d . . . H13 H 1.2726 0.4854 0.0593 0.078 Uiso 1 1 calc R . . C14 C 1.1071(4) 0.4526(4) 0.1384(2) 0.0548(10) Uani 1 1 d . . . H14 H 1.1732 0.5178 0.1792 0.066 Uiso 1 1 calc R . . C15 C 0.5336(4) 0.1379(4) 0.2238(2) 0.0502(9) Uani 1 1 d . . . H15A H 0.4710 0.0583 0.1860 0.060 Uiso 1 1 calc R . . H15B H 0.4615 0.1702 0.2530 0.060 Uiso 1 1 calc R . . C16 C 0.6418(5) 0.0938(4) 0.2831(2) 0.0466(8) Uani 1 1 d . . . C18 C 0.8569(5) 0.1097(4) 0.3606(2) 0.0544(9) Uani 1 1 d . . . H18 H 0.9611 0.1461 0.3853 0.065 Uiso 1 1 calc R . . C17 C 0.7501(5) -0.0167(4) 0.3749(2) 0.0607(11) Uani 1 1 d . . . H17 H 0.7646 -0.0837 0.4105 0.073 Uiso 1 1 calc R . . C19 C 0.4592(6) -0.1429(5) 0.3192(3) 0.0870(15) Uani 1 1 d . . . H19B H 0.4726 -0.2226 0.3469 0.130 Uiso 1 1 calc R . . H19A H 0.4213 -0.1711 0.2625 0.130 Uiso 1 1 calc R . . H19C H 0.3832 -0.1126 0.3451 0.130 Uiso 1 1 calc R . . N7 N 0.0734(6) 0.7976(6) 0.2065(3) 0.1062(16) Uani 1 1 d . . . C20 C 0.0754(6) 0.9061(6) 0.1893(3) 0.0755(13) Uani 1 1 d . . . C21 C 0.0732(6) 1.0437(6) 0.1654(4) 0.1040(19) Uani 1 1 d . . . H21A H 0.1760 1.1154 0.1808 0.156 Uiso 1 1 calc R . . H21B H -0.0064 1.0665 0.1926 0.156 Uiso 1 1 calc R . . H21C H 0.0486 1.0409 0.1069 0.156 Uiso 1 1 calc R . . Cl2 Cl 0.34926(15) 0.21966(13) 0.41860(7) 0.0703(3) Uani 1 1 d . . . O5 O 0.2777(5) 0.2347(6) 0.3422(2) 0.1415(19) Uani 1 1 d . . . O6 O 0.2891(7) 0.2660(5) 0.4837(2) 0.149(2) Uani 1 1 d . . . O7 O 0.5006(8) 0.2972(12) 0.4111(3) 0.288(6) Uani 1 1 d . . . O8 O 0.3685(17) 0.1026(8) 0.4315(5) 0.336(7) Uani 1 1 d . . . Cl1 Cl 0.61075(11) 0.79081(9) 0.08442(5) 0.0513(3) Uani 1 1 d . . . O1 O 0.5747(5) 0.6481(3) 0.0551(2) 0.0952(12) Uani 1 1 d . . . O2 O 0.7051(4) 0.8174(4) 0.1603(2) 0.1096(13) Uani 1 1 d . . . O3 O 0.4676(4) 0.8144(4) 0.0962(2) 0.1027(12) Uani 1 1 d . . . O4 O 0.6914(4) 0.8832(3) 0.0249(2) 0.0885(10) 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 0.0467(3) 0.0396(2) 0.0365(2) -0.00086(17) -0.00041(18) 0.01659(18) N1 0.0520(17) 0.0472(15) 0.0388(16) 0.0000(12) 0.0018(13) 0.0181(13) N2 0.0540(17) 0.0454(15) 0.0435(16) 0.0027(12) 0.0071(13) 0.0213(13) N3 0.0438(15) 0.0443(14) 0.0349(14) 0.0017(11) 0.0009(12) 0.0157(12) N4 0.0443(16) 0.0495(16) 0.0460(16) -0.0002(13) 0.0108(13) 0.0137(13) N5 0.0557(17) 0.0439(15) 0.0403(15) 0.0031(12) 0.0033(13) 0.0219(14) N6 0.079(2) 0.0461(16) 0.058(2) 0.0094(14) 0.0311(18) 0.0233(16) C1 0.061(2) 0.055(2) 0.056(2) -0.0049(18) -0.0084(19) 0.0234(18) C2 0.058(2) 0.070(3) 0.055(2) -0.003(2) -0.0046(18) 0.013(2) C3 0.064(3) 0.072(3) 0.052(2) -0.018(2) -0.002(2) 0.008(2) C4 0.078(3) 0.068(3) 0.055(2) -0.023(2) 0.006(2) 0.023(2) C5 0.061(2) 0.0480(19) 0.0387(19) -0.0002(15) 0.0071(17) 0.0186(17) C6 0.066(2) 0.056(2) 0.054(2) -0.0119(17) 0.0067(19) 0.0274(19) C7 0.054(2) 0.054(2) 0.052(2) 0.0051(16) 0.0075(17) 0.0287(17) C8 0.053(2) 0.056(2) 0.046(2) 0.0070(16) -0.0010(16) 0.0264(17) C9 0.051(2) 0.0488(18) 0.0379(18) -0.0078(15) -0.0002(15) 0.0156(16) C10 0.0480(18) 0.0446(17) 0.0401(18) 0.0040(14) 0.0076(15) 0.0184(15) C11 0.069(3) 0.067(2) 0.054(2) 0.0051(19) 0.009(2) 0.027(2) C12 0.069(3) 0.095(3) 0.059(3) 0.004(2) 0.020(2) 0.033(3) C13 0.052(2) 0.074(3) 0.073(3) 0.012(2) 0.018(2) 0.025(2) C14 0.050(2) 0.053(2) 0.057(2) 0.0012(17) 0.0089(18) 0.0116(17) C15 0.0455(19) 0.0494(19) 0.053(2) 0.0034(16) 0.0095(16) 0.0125(16) C16 0.064(2) 0.0437(17) 0.0399(18) 0.0029(14) 0.0151(16) 0.0259(17) C18 0.072(2) 0.055(2) 0.043(2) 0.0031(16) 0.0011(18) 0.0305(19) C17 0.093(3) 0.062(2) 0.044(2) 0.0075(17) 0.016(2) 0.045(2) C19 0.090(4) 0.069(3) 0.101(4) 0.022(3) 0.036(3) 0.019(3) N7 0.117(4) 0.116(4) 0.094(3) 0.020(3) 0.010(3) 0.049(3) C20 0.066(3) 0.085(3) 0.073(3) 0.007(3) 0.005(2) 0.024(3) C21 0.076(3) 0.088(4) 0.135(5) 0.015(3) -0.010(3) 0.017(3) Cl2 0.0771(7) 0.0861(8) 0.0586(7) 0.0047(6) 0.0108(6) 0.0412(6) O5 0.095(3) 0.266(6) 0.079(3) -0.015(3) 0.006(2) 0.084(4) O6 0.276(6) 0.184(4) 0.079(2) 0.043(3) 0.087(3) 0.178(4) O7 0.114(5) 0.543(16) 0.096(4) -0.038(6) -0.014(3) -0.016(7) O8 0.73(2) 0.207(6) 0.233(8) 0.094(6) 0.250(11) 0.315(10) Cl1 0.0543(5) 0.0459(5) 0.0501(5) -0.0031(4) 0.0013(4) 0.0142(4) O1 0.131(3) 0.0528(17) 0.094(2) -0.0063(16) 0.037(2) 0.0163(18) O2 0.083(2) 0.138(3) 0.077(2) 0.006(2) -0.0299(18) 0.008(2) O3 0.076(2) 0.140(3) 0.106(3) -0.003(2) 0.011(2) 0.056(2) O4 0.113(3) 0.0647(18) 0.085(2) 0.0185(16) 0.030(2) 0.0216(18) _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 1.968(3) . ? Cu1 N5 1.987(3) . ? Cu1 N2 2.020(3) . ? Cu1 N3 2.053(2) . ? Cu1 N4 2.137(3) . ? N1 C5 1.336(5) . ? N1 C1 1.348(5) . ? N2 C7 1.480(4) . ? N2 C6 1.480(4) . ? N2 H22 0.8774 . ? N3 C9 1.474(4) . ? N3 C8 1.486(4) . ? N3 C15 1.492(4) . ? N4 C10 1.330(4) . ? N4 C14 1.366(4) . ? N5 C16 1.326(4) . ? N5 C18 1.376(4) . ? N6 C16 1.348(4) . ? N6 C17 1.425(5) . ? N6 C19 1.431(5) . ? C1 C2 1.358(5) . ? C1 H1 0.9300 . ? C2 C3 1.363(6) . ? C2 H2 0.9300 . ? C3 C4 1.380(6) . ? C3 H3 0.9300 . ? C4 C5 1.383(5) . ? C4 H4 0.9300 . ? C5 C6 1.511(5) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.511(5) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8B 0.9700 . ? C8 H8A 0.9700 . ? C9 C10 1.484(5) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.408(5) . ? C11 C12 1.368(6) . ? C11 H11 0.9300 . ? C12 C13 1.361(6) . ? C12 H12 0.9300 . ? C13 C14 1.364(6) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 C16 1.492(5) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C18 C17 1.333(5) . ? C18 H18 0.9300 . ? C17 H17 0.9300 . ? C19 H19B 0.9600 . ? C19 H19A 0.9600 . ? C19 H19C 0.9600 . ? N7 C20 1.119(6) . ? C20 C21 1.442(7) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? Cl2 O8 1.258(6) . ? Cl2 O7 1.328(6) . ? Cl2 O6 1.373(4) . ? Cl2 O5 1.389(4) . ? Cl1 O2 1.405(3) . ? Cl1 O1 1.410(3) . ? Cl1 O3 1.411(4) . ? Cl1 O4 1.418(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 N5 102.86(11) . . ? N1 Cu1 N2 83.06(11) . . ? N5 Cu1 N2 143.92(13) . . ? N1 Cu1 N3 166.80(12) . . ? N5 Cu1 N3 81.95(10) . . ? N2 Cu1 N3 85.93(11) . . ? N1 Cu1 N4 108.44(11) . . ? N5 Cu1 N4 106.65(12) . . ? N2 Cu1 N4 104.92(11) . . ? N3 Cu1 N4 81.44(11) . . ? C5 N1 C1 118.7(3) . . ? C5 N1 Cu1 114.7(2) . . ? C1 N1 Cu1 126.6(3) . . ? C7 N2 C6 117.0(3) . . ? C7 N2 Cu1 106.1(2) . . ? C6 N2 Cu1 108.4(2) . . ? C7 N2 H22 119.4 . . ? C6 N2 H22 100.6 . . ? Cu1 N2 H22 104.4 . . ? C9 N3 C8 112.9(3) . . ? C9 N3 C15 109.4(3) . . ? C8 N3 C15 112.6(3) . . ? C9 N3 Cu1 108.5(2) . . ? C8 N3 Cu1 106.1(2) . . ? C15 N3 Cu1 106.95(19) . . ? C10 N4 C14 118.0(3) . . ? C10 N4 Cu1 111.2(2) . . ? C14 N4 Cu1 130.8(2) . . ? C16 N5 C18 107.0(3) . . ? C16 N5 Cu1 110.6(2) . . ? C18 N5 Cu1 141.2(2) . . ? C16 N6 C17 107.0(3) . . ? C16 N6 C19 126.4(4) . . ? C17 N6 C19 126.5(3) . . ? N1 C1 C2 122.8(4) . . ? N1 C1 H1 118.6 . . ? C2 C1 H1 118.6 . . ? C1 C2 C3 118.5(4) . . ? C1 C2 H2 120.7 . . ? C3 C2 H2 120.7 . . ? C2 C3 C4 120.1(4) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C3 C4 C5 118.5(4) . . ? C3 C4 H4 120.8 . . ? C5 C4 H4 120.8 . . ? N1 C5 C4 121.4(4) . . ? N1 C5 C6 116.0(3) . . ? C4 C5 C6 122.6(4) . . ? N2 C6 C5 109.1(3) . . ? N2 C6 H6A 109.9 . . ? C5 C6 H6A 109.9 . . ? N2 C6 H6B 109.9 . . ? C5 C6 H6B 109.9 . . ? H6A C6 H6B 108.3 . . ? N2 C7 C8 107.0(3) . . ? N2 C7 H7A 110.3 . . ? C8 C7 H7A 110.3 . . ? N2 C7 H7B 110.3 . . ? C8 C7 H7B 110.3 . . ? H7A C7 H7B 108.6 . . ? N3 C8 C7 110.2(3) . . ? N3 C8 H8B 109.6 . . ? C7 C8 H8B 109.6 . . ? N3 C8 H8A 109.6 . . ? C7 C8 H8A 109.6 . . ? H8B C8 H8A 108.1 . . ? N3 C9 C10 112.7(3) . . ? N3 C9 H9A 109.1 . . ? C10 C9 H9A 109.1 . . ? N3 C9 H9B 109.1 . . ? C10 C9 H9B 109.1 . . ? H9A C9 H9B 107.8 . . ? N4 C10 C11 121.9(3) . . ? N4 C10 C9 117.9(3) . . ? C11 C10 C9 120.0(3) . . ? C12 C11 C10 118.8(4) . . ? C12 C11 H11 120.6 . . ? C10 C11 H11 120.6 . . ? C13 C12 C11 119.1(4) . . ? C13 C12 H12 120.5 . . ? C11 C12 H12 120.5 . . ? C12 C13 C14 120.4(4) . . ? C12 C13 H13 119.8 . . ? C14 C13 H13 119.8 . . ? C13 C14 N4 121.7(3) . . ? C13 C14 H14 119.1 . . ? N4 C14 H14 119.1 . . ? N3 C15 C16 106.4(3) . . ? N3 C15 H15A 110.5 . . ? C16 C15 H15A 110.5 . . ? N3 C15 H15B 110.5 . . ? C16 C15 H15B 110.5 . . ? H15A C15 H15B 108.6 . . ? N5 C16 N6 110.2(3) . . ? N5 C16 C15 121.2(3) . . ? N6 C16 C15 128.6(3) . . ? C17 C18 N5 110.5(4) . . ? C17 C18 H18 124.8 . . ? N5 C18 H18 124.8 . . ? C18 C17 N6 105.3(3) . . ? C18 C17 H17 127.3 . . ? N6 C17 H17 127.3 . . ? N6 C19 H19B 109.5 . . ? N6 C19 H19A 109.5 . . ? H19B C19 H19A 109.5 . . ? N6 C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? N7 C20 C21 178.1(6) . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? O8 Cl2 O7 97.5(8) . . ? O8 Cl2 O6 111.7(4) . . ? O7 Cl2 O6 113.4(5) . . ? O8 Cl2 O5 117.9(5) . . ? O7 Cl2 O5 100.8(4) . . ? O6 Cl2 O5 113.7(3) . . ? O2 Cl1 O1 110.4(3) . . ? O2 Cl1 O3 108.4(2) . . ? O1 Cl1 O3 109.3(2) . . ? O2 Cl1 O4 110.8(2) . . ? O1 Cl1 O4 108.6(2) . . ? O3 Cl1 O4 109.4(2) . . ? 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 N5 Cu1 N1 C5 -131.9(2) . . . . ? N2 Cu1 N1 C5 11.9(2) . . . . ? N3 Cu1 N1 C5 -21.8(6) . . . . ? N4 Cu1 N1 C5 115.4(2) . . . . ? N5 Cu1 N1 C1 50.0(3) . . . . ? N2 Cu1 N1 C1 -166.2(3) . . . . ? N3 Cu1 N1 C1 160.1(4) . . . . ? N4 Cu1 N1 C1 -62.7(3) . . . . ? N1 Cu1 N2 C7 -150.7(2) . . . . ? N5 Cu1 N2 C7 -48.3(3) . . . . ? N3 Cu1 N2 C7 22.0(2) . . . . ? N4 Cu1 N2 C7 102.0(2) . . . . ? N1 Cu1 N2 C6 -24.2(2) . . . . ? N5 Cu1 N2 C6 78.1(3) . . . . ? N3 Cu1 N2 C6 148.5(2) . . . . ? N4 Cu1 N2 C6 -131.5(2) . . . . ? N1 Cu1 N3 C9 162.0(4) . . . . ? N5 Cu1 N3 C9 -85.7(2) . . . . ? N2 Cu1 N3 C9 128.4(2) . . . . ? N4 Cu1 N3 C9 22.6(2) . . . . ? N1 Cu1 N3 C8 40.3(5) . . . . ? N5 Cu1 N3 C8 152.7(2) . . . . ? N2 Cu1 N3 C8 6.7(2) . . . . ? N4 Cu1 N3 C8 -99.0(2) . . . . ? N1 Cu1 N3 C15 -80.1(5) . . . . ? N5 Cu1 N3 C15 32.2(2) . . . . ? N2 Cu1 N3 C15 -113.7(2) . . . . ? N4 Cu1 N3 C15 140.5(2) . . . . ? N1 Cu1 N4 C10 178.2(2) . . . . ? N5 Cu1 N4 C10 68.1(2) . . . . ? N2 Cu1 N4 C10 -94.2(2) . . . . ? N3 Cu1 N4 C10 -10.8(2) . . . . ? N1 Cu1 N4 C14 -0.4(4) . . . . ? N5 Cu1 N4 C14 -110.6(3) . . . . ? N2 Cu1 N4 C14 87.1(3) . . . . ? N3 Cu1 N4 C14 170.5(3) . . . . ? N1 Cu1 N5 C16 144.7(2) . . . . ? N2 Cu1 N5 C16 48.8(3) . . . . ? N3 Cu1 N5 C16 -22.8(2) . . . . ? N4 Cu1 N5 C16 -101.3(3) . . . . ? N1 Cu1 N5 C18 -20.0(4) . . . . ? N2 Cu1 N5 C18 -115.9(4) . . . . ? N3 Cu1 N5 C18 172.5(4) . . . . ? N4 Cu1 N5 C18 94.0(4) . . . . ? C5 N1 C1 C2 0.1(6) . . . . ? Cu1 N1 C1 C2 178.1(3) . . . . ? N1 C1 C2 C3 -0.8(6) . . . . ? C1 C2 C3 C4 0.6(7) . . . . ? C2 C3 C4 C5 0.3(7) . . . . ? C1 N1 C5 C4 0.9(5) . . . . ? Cu1 N1 C5 C4 -177.4(3) . . . . ? C1 N1 C5 C6 -178.1(3) . . . . ? Cu1 N1 C5 C6 3.7(4) . . . . ? C3 C4 C5 N1 -1.0(6) . . . . ? C3 C4 C5 C6 177.9(4) . . . . ? C7 N2 C6 C5 151.1(3) . . . . ? Cu1 N2 C6 C5 31.3(4) . . . . ? N1 C5 C6 N2 -23.8(5) . . . . ? C4 C5 C6 N2 157.2(3) . . . . ? C6 N2 C7 C8 -167.1(3) . . . . ? Cu1 N2 C7 C8 -46.0(3) . . . . ? C9 N3 C8 C7 -153.3(3) . . . . ? C15 N3 C8 C7 82.2(3) . . . . ? Cu1 N3 C8 C7 -34.5(3) . . . . ? N2 C7 C8 N3 54.9(3) . . . . ? C8 N3 C9 C10 86.1(3) . . . . ? C15 N3 C9 C10 -147.7(3) . . . . ? Cu1 N3 C9 C10 -31.3(3) . . . . ? C14 N4 C10 C11 -0.1(5) . . . . ? Cu1 N4 C10 C11 -179.0(3) . . . . ? C14 N4 C10 C9 174.6(3) . . . . ? Cu1 N4 C10 C9 -4.2(4) . . . . ? N3 C9 C10 N4 24.3(4) . . . . ? N3 C9 C10 C11 -160.9(3) . . . . ? N4 C10 C11 C12 2.3(6) . . . . ? C9 C10 C11 C12 -172.3(4) . . . . ? C10 C11 C12 C13 -1.9(6) . . . . ? C11 C12 C13 C14 -0.5(7) . . . . ? C12 C13 C14 N4 2.7(6) . . . . ? C10 N4 C14 C13 -2.4(5) . . . . ? Cu1 N4 C14 C13 176.2(3) . . . . ? C9 N3 C15 C16 83.2(3) . . . . ? C8 N3 C15 C16 -150.4(3) . . . . ? Cu1 N3 C15 C16 -34.2(3) . . . . ? C18 N5 C16 N6 -0.1(4) . . . . ? Cu1 N5 C16 N6 -170.2(2) . . . . ? C18 N5 C16 C15 178.4(3) . . . . ? Cu1 N5 C16 C15 8.3(4) . . . . ? C17 N6 C16 N5 0.2(4) . . . . ? C19 N6 C16 N5 178.3(4) . . . . ? C17 N6 C16 C15 -178.2(4) . . . . ? C19 N6 C16 C15 -0.1(7) . . . . ? N3 C15 C16 N5 18.4(5) . . . . ? N3 C15 C16 N6 -163.4(4) . . . . ? C16 N5 C18 C17 0.0(4) . . . . ? Cu1 N5 C18 C17 165.1(3) . . . . ? N5 C18 C17 N6 0.1(4) . . . . ? C16 N6 C17 C18 -0.2(4) . . . . ? C19 N6 C17 C18 -178.3(4) . . . . ? _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 28.43 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 0.804 _refine_diff_density_min -0.725 _refine_diff_density_rms 0.081