# 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_Complex2 #TrackingRef '12decb.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 9-propargylguanine+CuBr2 _chemical_melting_point ? _chemical_formula_moiety 'C16 H14 Br4 Cu3 N10 O2' _chemical_formula_sum 'C16 H14 Br4 Cu3 N10 O2' _chemical_formula_weight 888.63 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 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' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M ' P 21/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.0201(12) _cell_length_b 19.173(3) _cell_length_c 7.3148(11) _cell_angle_alpha 90.00 _cell_angle_beta 93.877(3) _cell_angle_gamma 90.00 _cell_volume 1122.2(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2177 _cell_measurement_theta_min 2.12 _cell_measurement_theta_max 26.00 _exptl_crystal_description needle _exptl_crystal_colour 'dark green' _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.630 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 846 _exptl_absorpt_coefficient_mu 9.979 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.2074 _exptl_absorpt_correction_T_max 0.2402 _exptl_absorpt_process_details '(North et al., 1968)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6061 _diffrn_reflns_av_R_equivalents 0.0364 _diffrn_reflns_av_sigmaI/netI 0.0391 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2177 _reflns_number_gt 1890 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART 5.628 (Bruker, 2003)' _computing_cell_refinement 'SMART 5.628 (Bruker, 2003)' _computing_data_reduction 'SAINT+ 6.45 (Bruker, 2003)' _computing_structure_solution Sir92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'diamond 3.1d' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.1040P)^2^+23.5270P] 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 2177 _refine_ls_number_parameters 160 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0718 _refine_ls_R_factor_gt 0.0647 _refine_ls_wR_factor_ref 0.1999 _refine_ls_wR_factor_gt 0.1929 _refine_ls_goodness_of_fit_ref 1.140 _refine_ls_restrained_S_all 1.140 _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 Cu2 Cu 0.0000 0.0000 0.0000 0.0085(4) Uani 1 2 d S . . Cu1 Cu 0.54743(14) 0.23229(6) 0.46233(15) 0.0128(3) Uani 1 1 d . . . Br1 Br 0.75229(12) 0.23603(6) 0.73002(14) 0.0224(3) Uani 1 1 d . . . Br2 Br -0.09315(15) -0.06096(6) 0.26469(16) 0.0328(4) Uani 1 1 d . . . O6 O 0.3685(9) -0.0445(3) 0.1005(9) 0.0156(14) Uani 1 1 d . . . N2 N 0.7412(10) 0.0839(4) 0.4724(11) 0.0159(16) Uani 1 1 d . . . H2A H 0.7695 0.1193 0.5398 0.019 Uiso 1 1 calc R . . H2B H 0.8125 0.0514 0.4560 0.019 Uiso 1 1 calc R . . N1 N 0.5465(10) 0.0217(4) 0.2914(10) 0.0106(15) Uani 1 1 d . . . H1 H 0.6229 -0.0096 0.2859 0.013 Uiso 1 1 calc R . . N9 N 0.1870(9) 0.1595(4) 0.3379(10) 0.0090(14) Uani 1 1 d . . . N3 N 0.4788(9) 0.1302(4) 0.4206(9) 0.0076(14) Uani 1 1 d . . . C2 C 0.5869(11) 0.0795(5) 0.3936(12) 0.0119(17) Uani 1 1 d . . . C4 C 0.3242(11) 0.1176(4) 0.3367(11) 0.0097(17) Uani 1 1 d . . . C6 C 0.3933(12) 0.0080(5) 0.1945(12) 0.0134(18) Uani 1 1 d . . . C10 C 0.3062(11) 0.2707(4) 0.4430(12) 0.0098(17) Uani 1 1 d . . . C9 C 0.1658(11) 0.2219(5) 0.4537(12) 0.0104(17) Uani 1 1 d . . . H9A H 0.0624 0.2453 0.4140 0.012 Uiso 1 1 calc R . . H9B H 0.1581 0.2074 0.5799 0.012 Uiso 1 1 calc R . . N7 N 0.1123(9) 0.0692(4) 0.1613(10) 0.0110(15) Uani 1 1 d . . . C8 C 0.0617(11) 0.1279(5) 0.2300(11) 0.0118(17) Uani 1 1 d . . . H8 H -0.0455 0.1459 0.2086 0.014 Uiso 1 1 calc R . . C5 C 0.2778(12) 0.0619(4) 0.2284(11) 0.0112(18) Uani 1 1 d . . . C11 C 0.3988(12) 0.3206(5) 0.4372(13) 0.0151(18) Uani 1 1 d . . . H11 H 0.4697 0.3589 0.4328 0.018 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 Cu2 0.0056(7) 0.0084(7) 0.0110(7) -0.0043(5) -0.0031(5) -0.0018(5) Cu1 0.0099(6) 0.0091(6) 0.0188(6) -0.0016(4) -0.0023(4) -0.0006(4) Br1 0.0183(6) 0.0288(6) 0.0198(6) -0.0040(4) -0.0007(4) -0.0021(4) Br2 0.0320(7) 0.0321(7) 0.0336(7) -0.0018(5) -0.0026(5) 0.0009(5) O6 0.026(4) 0.008(3) 0.014(3) -0.004(2) 0.001(3) -0.001(3) N2 0.016(4) 0.012(4) 0.019(4) -0.001(3) -0.002(3) 0.004(3) N1 0.015(4) 0.006(3) 0.011(4) 0.003(3) 0.003(3) 0.004(3) N9 0.006(3) 0.010(4) 0.012(4) -0.005(3) 0.000(3) -0.003(3) N3 0.007(3) 0.008(3) 0.008(3) -0.001(3) 0.000(3) 0.002(3) C2 0.012(4) 0.012(4) 0.011(4) 0.007(3) 0.003(3) 0.000(3) C4 0.014(4) 0.007(4) 0.008(4) 0.000(3) 0.004(3) -0.002(3) C6 0.021(5) 0.008(4) 0.011(4) 0.003(3) 0.003(4) -0.001(3) C10 0.013(4) 0.007(4) 0.008(4) -0.003(3) -0.005(3) 0.002(3) C9 0.009(4) 0.010(4) 0.012(4) -0.007(3) 0.000(3) -0.003(3) N7 0.011(4) 0.011(4) 0.011(4) 0.001(3) -0.001(3) -0.002(3) C8 0.010(4) 0.017(5) 0.008(4) -0.006(3) 0.001(3) -0.003(3) C5 0.020(5) 0.008(4) 0.006(4) 0.003(3) 0.004(3) -0.004(3) C11 0.016(4) 0.012(4) 0.017(4) 0.000(4) -0.001(4) 0.004(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 Cu2 N7 1.955(7) 3 ? Cu2 N7 1.955(7) . ? Cu2 Br2 2.4225(13) . ? Cu2 Br2 2.4225(13) 3 ? Cu1 N3 2.050(7) . ? Cu1 C10 2.066(9) . ? Cu1 C11 2.073(9) . ? Cu1 Br1 2.4706(15) . ? Cu1 Br1 2.5166(15) 4_565 ? Br1 Cu1 2.5166(15) 4_566 ? O6 C6 1.227(11) . ? N2 C2 1.332(12) . ? N1 C2 1.364(12) . ? N1 C6 1.401(12) . ? N9 C4 1.364(12) . ? N9 C8 1.376(11) . ? N9 C9 1.481(11) . ? N3 C2 1.326(12) . ? N3 C4 1.367(11) . ? C4 C5 1.365(12) . ? C6 C5 1.421(13) . ? C10 C11 1.214(14) . ? C10 C9 1.471(12) . ? N7 C8 1.308(12) . ? N7 C5 1.391(12) . ? 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 N7 Cu2 N7 180.0(5) 3 . ? N7 Cu2 Br2 90.0(2) 3 . ? N7 Cu2 Br2 90.0(2) . . ? N7 Cu2 Br2 90.0(2) 3 3 ? N7 Cu2 Br2 90.0(2) . 3 ? Br2 Cu2 Br2 180.00(7) . 3 ? N3 Cu1 C10 95.1(3) . . ? N3 Cu1 C11 128.3(3) . . ? C10 Cu1 C11 34.1(4) . . ? N3 Cu1 Br1 107.7(2) . . ? C10 Cu1 Br1 127.8(2) . . ? C11 Cu1 Br1 113.2(3) . . ? N3 Cu1 Br1 108.1(2) . 4_565 ? C10 Cu1 Br1 121.2(3) . 4_565 ? C11 Cu1 Br1 98.1(3) . 4_565 ? Br1 Cu1 Br1 95.66(5) . 4_565 ? Cu1 Br1 Cu1 96.47(5) . 4_566 ? C2 N1 C6 126.7(8) . . ? C4 N9 C8 107.1(7) . . ? C4 N9 C9 127.1(7) . . ? C8 N9 C9 125.2(7) . . ? C2 N3 C4 112.6(7) . . ? C2 N3 Cu1 123.4(6) . . ? C4 N3 Cu1 117.6(6) . . ? N3 C2 N2 119.1(9) . . ? N3 C2 N1 123.0(8) . . ? N2 C2 N1 117.9(8) . . ? N9 C4 N3 126.8(8) . . ? N9 C4 C5 106.1(8) . . ? N3 C4 C5 127.0(8) . . ? O6 C6 N1 122.7(9) . . ? O6 C6 C5 127.7(9) . . ? N1 C6 C5 109.6(8) . . ? C11 C10 C9 167.5(9) . . ? C11 C10 Cu1 73.2(6) . . ? C9 C10 Cu1 119.1(6) . . ? C10 C9 N9 111.4(7) . . ? C8 N7 C5 105.3(7) . . ? C8 N7 Cu2 132.3(6) . . ? C5 N7 Cu2 122.3(6) . . ? N7 C8 N9 111.5(8) . . ? C4 C5 N7 110.0(8) . . ? C4 C5 C6 121.0(9) . . ? N7 C5 C6 129.0(8) . . ? C10 C11 Cu1 72.7(6) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 3.406 _refine_diff_density_min -2.938 _refine_diff_density_rms 0.366 _database_code_depnum_ccdc_archive 'CCDC 808671' ####################################################################### # # 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_Complex1 #TrackingRef '26apra.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 9-propargylguanine+CuCl2 _chemical_melting_point ? _chemical_formula_moiety 'C16 H14 Cl4 Cu3 N10 O2' _chemical_formula_sum 'C16 H14 Cl4 Cu3 N10 O2' _chemical_formula_weight 710.79 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 monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.877(2) _cell_length_b 19.236(5) _cell_length_c 7.151(2) _cell_angle_alpha 90.00 _cell_angle_beta 93.808(4) _cell_angle_gamma 90.00 _cell_volume 1081.1(5) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2653 _cell_measurement_theta_min 2.12 _cell_measurement_theta_max 28.37 _exptl_crystal_description needle _exptl_crystal_colour 'dark green' _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.183 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 702 _exptl_absorpt_coefficient_mu 3.460 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.5033 _exptl_absorpt_correction_T_max 0.5445 _exptl_absorpt_process_details '(North et al., 1968)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6879 _diffrn_reflns_av_R_equivalents 0.0545 _diffrn_reflns_av_sigmaI/netI 0.0560 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 28.37 _reflns_number_total 2653 _reflns_number_gt 2141 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART 5.628 (Bruker, 2003)' _computing_cell_refinement 'SMART 5.628 (Bruker, 2003)' _computing_data_reduction 'SAINT+ 6.45 (Bruker, 2003)' _computing_structure_solution Sir92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'diamond 3.1d' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.1656P)^2^+2.5195P] 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 2653 _refine_ls_number_parameters 160 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0781 _refine_ls_R_factor_gt 0.0550 _refine_ls_wR_factor_ref 0.2367 _refine_ls_wR_factor_gt 0.1692 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _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 Cu2 Cu 0.0000 0.0000 0.5000 0.0158(3) Uani 1 2 d S . . Cu1 Cu 0.55104(9) 0.23466(4) 0.96227(10) 0.0210(3) Uani 1 1 d . . . Cl2 Cl 0.09519(16) 0.05573(7) 0.23854(18) 0.0194(3) Uani 1 1 d . . . O6 O 0.3691(5) -0.0429(2) 0.6054(6) 0.0213(8) Uani 1 1 d . . . N7 N 0.1096(6) 0.0710(2) 0.6613(6) 0.0173(9) Uani 1 1 d . . . N9 N 0.1843(6) 0.1620(2) 0.8395(6) 0.0147(9) Uani 1 1 d . . . N3 N 0.4796(6) 0.1327(2) 0.9257(6) 0.0157(9) Uani 1 1 d . . . N1 N 0.5515(6) 0.0240(2) 0.7957(6) 0.0170(9) Uani 1 1 d . . . H1 H 0.6301 -0.0068 0.7893 0.020 Uiso 1 1 calc R . . C2 C 0.5905(7) 0.0820(3) 0.8987(7) 0.0191(11) Uani 1 1 d . . . N2 N 0.7483(6) 0.0868(3) 0.9789(7) 0.0205(10) Uani 1 1 d . . . H2A H 0.7771 0.1223 1.0470 0.025 Uiso 1 1 calc R . . H2B H 0.8211 0.0544 0.9625 0.025 Uiso 1 1 calc R . . C4 C 0.3242(7) 0.1196(3) 0.8398(7) 0.0149(10) Uani 1 1 d . . . C9 C 0.1630(7) 0.2244(3) 0.9549(8) 0.0196(11) Uani 1 1 d . . . H9A H 0.1547 0.2107 1.0845 0.024 Uiso 1 1 calc R . . H9B H 0.0580 0.2477 0.9133 0.024 Uiso 1 1 calc R . . C5 C 0.2765(7) 0.0635(3) 0.7317(8) 0.0171(10) Uani 1 1 d . . . C10 C 0.3075(8) 0.2733(3) 0.9425(8) 0.0208(11) Uani 1 1 d . . . C11 C 0.4006(7) 0.3231(3) 0.9299(8) 0.0178(10) Uani 1 1 d . . . H11 H 0.4720 0.3612 0.9202 0.021 Uiso 1 1 calc R . . C8 C 0.0571(7) 0.1306(3) 0.7288(7) 0.0178(10) Uani 1 1 d . . . H8 H -0.0514 0.1488 0.7048 0.021 Uiso 1 1 calc R . . Cl1 Cl 0.75019(18) 0.23818(7) 1.2257(2) 0.0221(4) Uani 1 1 d . . . C6 C 0.3944(8) 0.0099(3) 0.6992(8) 0.0184(11) 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 Cu2 0.0147(5) 0.0163(5) 0.0161(5) -0.0037(3) -0.0016(4) -0.0023(3) Cu1 0.0183(5) 0.0175(5) 0.0267(5) -0.0027(3) -0.0028(3) -0.0003(2) Cl2 0.0184(6) 0.0185(7) 0.0210(7) -0.0012(5) -0.0014(5) 0.0011(5) O6 0.026(2) 0.017(2) 0.022(2) -0.0009(15) 0.0032(15) -0.0006(16) N7 0.019(2) 0.013(2) 0.020(2) -0.0013(17) -0.0010(17) -0.0052(17) N9 0.018(2) 0.014(2) 0.0116(19) -0.0027(16) -0.0024(15) -0.0007(17) N3 0.019(2) 0.012(2) 0.016(2) -0.0008(16) 0.0005(16) 0.0004(16) N1 0.018(2) 0.016(2) 0.018(2) 0.0016(17) 0.0055(16) 0.0043(17) C2 0.019(2) 0.024(3) 0.014(2) 0.007(2) 0.0005(18) 0.001(2) N2 0.016(2) 0.021(2) 0.025(2) -0.0031(19) -0.0005(17) 0.0061(18) C4 0.020(2) 0.014(2) 0.011(2) 0.0022(18) 0.0035(17) -0.0001(19) C9 0.023(3) 0.015(2) 0.021(3) -0.005(2) 0.001(2) -0.001(2) C5 0.015(2) 0.019(3) 0.017(2) 0.0043(19) 0.0026(18) -0.0013(19) C10 0.024(3) 0.021(3) 0.017(3) -0.004(2) -0.004(2) 0.002(2) C11 0.018(2) 0.016(3) 0.019(3) -0.0038(19) 0.0023(19) 0.006(2) C8 0.020(3) 0.018(3) 0.015(2) -0.0017(19) 0.0008(19) -0.002(2) Cl1 0.0202(7) 0.0263(8) 0.0195(7) -0.0018(5) -0.0024(5) -0.0029(5) C6 0.025(3) 0.016(2) 0.015(3) -0.0029(19) 0.008(2) 0.004(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu2 N7 1.951(4) . ? Cu2 N7 1.951(4) 3_556 ? Cu2 Cl2 2.3224(14) . ? Cu2 Cl2 2.3224(14) 3_556 ? Cu1 N3 2.052(5) . ? Cu1 C10 2.054(6) . ? Cu1 C11 2.077(5) . ? Cu1 Cl1 2.3709(16) . ? Cu1 Cl1 2.4390(17) 4_565 ? O6 C6 1.227(7) . ? N7 C8 1.321(7) . ? N7 C5 1.384(7) . ? N9 C4 1.371(7) . ? N9 C8 1.375(7) . ? N9 C9 1.473(7) . ? N3 C2 1.332(7) . ? N3 C4 1.356(7) . ? N1 C2 1.361(8) . ? N1 C6 1.403(8) . ? C2 N2 1.337(7) . ? C4 C5 1.366(8) . ? C9 C10 1.483(8) . ? C5 C6 1.417(8) . ? C10 C11 1.213(9) . ? Cl1 Cu1 2.4390(17) 4_566 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N7 Cu2 N7 180.0(2) . 3_556 ? N7 Cu2 Cl2 89.94(14) . . ? N7 Cu2 Cl2 90.06(14) 3_556 . ? N7 Cu2 Cl2 90.06(14) . 3_556 ? N7 Cu2 Cl2 89.94(14) 3_556 3_556 ? Cl2 Cu2 Cl2 180.00(6) . 3_556 ? N3 Cu1 C10 95.2(2) . . ? N3 Cu1 C11 128.2(2) . . ? C10 Cu1 C11 34.1(2) . . ? N3 Cu1 Cl1 106.86(13) . . ? C10 Cu1 Cl1 127.59(16) . . ? C11 Cu1 Cl1 114.05(16) . . ? N3 Cu1 Cl1 107.44(13) . 4_565 ? C10 Cu1 Cl1 121.05(17) . 4_565 ? C11 Cu1 Cl1 97.80(16) . 4_565 ? Cl1 Cu1 Cl1 97.06(6) . 4_565 ? C8 N7 C5 105.7(5) . . ? C8 N7 Cu2 133.4(4) . . ? C5 N7 Cu2 121.0(4) . . ? C4 N9 C8 107.1(4) . . ? C4 N9 C9 127.3(5) . . ? C8 N9 C9 125.1(5) . . ? C2 N3 C4 112.3(5) . . ? C2 N3 Cu1 122.8(4) . . ? C4 N3 Cu1 117.8(4) . . ? C2 N1 C6 125.7(5) . . ? N3 C2 N2 119.2(5) . . ? N3 C2 N1 123.5(5) . . ? N2 C2 N1 117.3(5) . . ? N3 C4 C5 127.5(5) . . ? N3 C4 N9 126.3(5) . . ? C5 C4 N9 106.2(5) . . ? N9 C9 C10 111.5(5) . . ? C4 C5 N7 110.0(5) . . ? C4 C5 C6 120.6(5) . . ? N7 C5 C6 129.3(5) . . ? C11 C10 C9 167.1(6) . . ? C11 C10 Cu1 74.0(4) . . ? C9 C10 Cu1 118.9(4) . . ? C10 C11 Cu1 71.9(4) . . ? N7 C8 N9 111.0(5) . . ? Cu1 Cl1 Cu1 97.77(6) . 4_566 ? O6 C6 N1 122.3(5) . . ? O6 C6 C5 127.4(6) . . ? N1 C6 C5 110.2(5) . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 2.003 _refine_diff_density_min -2.096 _refine_diff_density_rms 0.378 _database_code_depnum_ccdc_archive 'CCDC 808672' ####################################################################### # # 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_Complex3 #TrackingRef '29sepam.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 9-allylguanine+CuCl2 _chemical_melting_point ? _chemical_formula_moiety 'C48 H54 Cl6 Cu3 N30 O6, 4(C H4 O)' _chemical_formula_sum 'C52 H70 Cl6 Cu3 N30 O10' _chemical_formula_weight 1678.70 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.0805(12) _cell_length_b 10.2327(12) _cell_length_c 17.619(2) _cell_angle_alpha 74.604(3) _cell_angle_beta 78.168(2) _cell_angle_gamma 87.898(2) _cell_volume 1714.6(4) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6571 _cell_measurement_theta_min 2.06 _cell_measurement_theta_max 26.00 _exptl_crystal_description needle _exptl_crystal_colour 'dark green' _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.626 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 861 _exptl_absorpt_coefficient_mu 1.234 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.7644 _exptl_absorpt_correction_T_max 0.7904 _exptl_absorpt_process_details '(North et al., 1968)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9545 _diffrn_reflns_av_R_equivalents 0.0252 _diffrn_reflns_av_sigmaI/netI 0.0472 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 26.00 _reflns_number_total 6571 _reflns_number_gt 5685 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART 5.628 (Bruker, 2003)' _computing_cell_refinement 'SMART 5.628 (Bruker, 2003)' _computing_data_reduction 'SAINT+ 6.45 (Bruker, 2003)' _computing_structure_solution Sir92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'diamond 3.1d' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0972P)^2^+0.7134P] 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 6571 _refine_ls_number_parameters 456 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0593 _refine_ls_R_factor_gt 0.0509 _refine_ls_wR_factor_ref 0.1594 _refine_ls_wR_factor_gt 0.1418 _refine_ls_goodness_of_fit_ref 1.141 _refine_ls_restrained_S_all 1.141 _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 C2 C -0.1161(3) 0.5393(3) -0.0787(2) 0.0176(7) Uani 1 1 d . . . C2A C 0.6505(3) 0.5012(4) -0.3500(2) 0.0186(7) Uani 1 1 d . . . C2B C -0.2525(3) 0.2577(3) -0.4716(2) 0.0180(7) Uani 1 1 d . . . C4 C -0.1543(3) 0.3647(3) 0.0299(2) 0.0171(7) Uani 1 1 d . . . C4A C 0.4936(4) 0.3953(4) -0.2458(2) 0.0259(8) Uani 1 1 d . A . C4B C -0.2283(4) 0.1824(4) -0.3459(2) 0.0221(7) Uani 1 1 d . A . C5 C -0.0999(3) 0.2711(3) -0.0111(2) 0.0159(7) Uani 1 1 d . . . C5A C 0.4008(3) 0.3827(3) -0.2912(2) 0.0168(7) Uani 1 1 d . . . C5B C -0.1037(3) 0.2455(3) -0.3589(2) 0.0161(7) Uani 1 1 d . . . C6 C -0.0447(3) 0.3140(3) -0.0940(2) 0.0156(7) Uani 1 1 d . . . C6A C 0.4374(3) 0.4292(3) -0.37617(19) 0.0156(7) Uani 1 1 d . . . C6B C -0.0419(4) 0.3183(4) -0.4372(2) 0.0223(7) Uani 1 1 d . . . C8 C -0.1605(3) 0.1596(3) 0.1126(2) 0.0191(7) Uani 1 1 d . . . H8 H -0.1764 0.0895 0.1597 0.023 Uiso 1 1 calc R . . C8A C 0.3053(4) 0.2966(4) -0.1672(2) 0.0280(9) Uani 1 1 d . A . H8A H 0.2425 0.2549 -0.1212 0.034 Uiso 1 1 calc R . . C8B C -0.1541(4) 0.1430(4) -0.2331(2) 0.0356(10) Uani 1 1 d . A . H8B H -0.1503 0.1101 -0.1791 0.043 Uiso 1 1 calc R . . C9 C -0.2414(4) 0.3494(4) 0.1779(2) 0.0312(9) Uani 1 1 d . . . H9A H -0.1772 0.3272 0.2133 0.037 Uiso 1 1 calc R . . H9B H -0.2426 0.4474 0.1586 0.037 Uiso 1 1 calc R . . C10 C -0.3771(5) 0.3004(5) 0.2245(2) 0.0389(10) Uani 1 1 d . . . H10 H -0.4494 0.3205 0.1982 0.047 Uiso 1 1 calc R . . C11 C -0.4040(6) 0.2305(5) 0.3002(3) 0.0518(13) Uani 1 1 d . . . H11A H -0.3344 0.2083 0.3285 0.062 Uiso 1 1 calc R . . H11B H -0.4927 0.2031 0.3255 0.062 Uiso 1 1 calc R . . N1 N -0.0604(3) 0.4522(3) -0.12438(17) 0.0178(6) Uani 1 1 d . . . H1 H -0.0337 0.4861 -0.1753 0.021 Uiso 1 1 calc R . . N1A N 0.5653(3) 0.4920(3) -0.40032(16) 0.0154(6) Uani 1 1 d . . . H1A H 0.5933 0.5280 -0.4509 0.018 Uiso 1 1 calc R . . N1B N -0.1283(3) 0.3229(3) -0.49075(17) 0.0213(6) Uani 1 1 d . . . H1B H -0.1016 0.3703 -0.5395 0.026 Uiso 1 1 calc R . . N2 N -0.1196(3) 0.6708(3) -0.1173(2) 0.0273(7) Uani 1 1 d . . . H2A H -0.1532 0.7284 -0.0911 0.033 Uiso 1 1 calc R . . H2B H -0.0882 0.6976 -0.1682 0.033 Uiso 1 1 calc R . . N2A N 0.7709(3) 0.5635(3) -0.38312(18) 0.0215(6) Uani 1 1 d . . . H2A1 H 0.8264 0.5704 -0.3532 0.026 Uiso 1 1 calc R . . H2A2 H 0.7929 0.5966 -0.4343 0.026 Uiso 1 1 calc R . . N2B N -0.3192(3) 0.2719(3) -0.53294(18) 0.0215(6) Uani 1 1 d . . . H2B1 H -0.3965 0.2320 -0.5245 0.026 Uiso 1 1 calc R . . H2B2 H -0.2841 0.3208 -0.5802 0.026 Uiso 1 1 calc R . . N3 N -0.1649(3) 0.4995(3) -0.00009(17) 0.0188(6) Uani 1 1 d . . . N3A N 0.6197(3) 0.4513(4) -0.27114(18) 0.0270(7) Uani 1 1 d . . . N3B N -0.3056(3) 0.1837(3) -0.39998(18) 0.0275(7) Uani 1 1 d . . . N7 N -0.1031(3) 0.1441(3) 0.04119(16) 0.0178(6) Uani 1 1 d . . . N7A N 0.2838(3) 0.3228(3) -0.24113(16) 0.0163(6) Uani 1 1 d . . . N7B N -0.0603(3) 0.2202(3) -0.28677(16) 0.0162(6) Uani 1 1 d . . . N9 N -0.1939(3) 0.2924(3) 0.10875(17) 0.0196(6) Uani 1 1 d . . . N9A N 0.4324(3) 0.3393(4) -0.16752(19) 0.0388(10) Uani 1 1 d . . . N9B N -0.2581(4) 0.1165(5) -0.2657(2) 0.0514(12) Uani 1 1 d . . . O6 O 0.0114(2) 0.2406(2) -0.13695(14) 0.0160(5) Uani 1 1 d . . . O6A O 0.3704(2) 0.4212(2) -0.42604(13) 0.0185(5) Uani 1 1 d . . . O6B O 0.0709(3) 0.3715(3) -0.45931(16) 0.0361(7) Uani 1 1 d . . . Cl1 Cl 0.21658(9) 0.08809(8) -0.30085(5) 0.0235(2) Uani 1 1 d . . . Cl2 Cl 0.06422(8) 0.51439(8) -0.30945(5) 0.0172(2) Uani 1 1 d . . . Cl3 Cl -0.19033(8) -0.07509(8) -0.02844(5) 0.0194(2) Uani 1 1 d . . . Cu1 Cu 0.11534(4) 0.27866(4) -0.27168(2) 0.01531(15) Uani 1 1 d . . . Cu2 Cu 0.0000 0.0000 0.0000 0.01507(16) Uani 1 2 d S . . C9A C 0.4753(7) 0.3713(7) -0.0947(4) 0.0186(15) Uiso 0.516(5) 1 d P A 2 H9A1 H 0.5151 0.4618 -0.1100 0.022 Uiso 0.516(5) 1 calc PR A 2 H9A2 H 0.3973 0.3662 -0.0513 0.022 Uiso 0.516(5) 1 calc PR A 2 C10A C 0.5757(8) 0.2689(7) -0.0690(4) 0.0254(17) Uiso 0.516(5) 1 d P A 2 H10A H 0.6603 0.2721 -0.1026 0.031 Uiso 0.516(5) 1 calc PR A 2 C11A C 0.5511(8) 0.1736(8) -0.0008(5) 0.0304(18) Uiso 0.516(5) 1 d P A 2 H11C H 0.4672 0.1684 0.0339 0.037 Uiso 0.516(5) 1 calc PR A 2 H11D H 0.6176 0.1115 0.0128 0.037 Uiso 0.516(5) 1 calc PR A 2 C9C C -0.4091(8) 0.0771(8) -0.2206(5) 0.0267(17) Uiso 0.516(5) 1 d P A 2 H9C1 H -0.4263 0.0941 -0.1678 0.032 Uiso 0.516(5) 1 calc PR A 2 H9C2 H -0.4725 0.1285 -0.2512 0.032 Uiso 0.516(5) 1 calc PR A 2 C10C C -0.4216(8) -0.0687(8) -0.2138(5) 0.0293(18) Uiso 0.516(5) 1 d P A 2 H10C H -0.5073 -0.1089 -0.1932 0.035 Uiso 0.516(5) 1 calc PR A 2 C11C C -0.3204(9) -0.1479(9) -0.2345(5) 0.040(2) Uiso 0.516(5) 1 d P A 2 H11E H -0.2332 -0.1117 -0.2553 0.048 Uiso 0.516(5) 1 calc PR A 2 H11F H -0.3371 -0.2393 -0.2283 0.048 Uiso 0.516(5) 1 calc PR A 2 C9B C 0.5004(7) 0.2917(7) -0.0979(4) 0.0165(15) Uiso 0.484(5) 1 d P A 1 H9B1 H 0.5942 0.2694 -0.1151 0.020 Uiso 0.484(5) 1 calc PR A 1 H9B2 H 0.4535 0.2132 -0.0589 0.020 Uiso 0.484(5) 1 calc PR A 1 C10B C 0.4903(9) 0.4121(9) -0.0641(6) 0.035(2) Uiso 0.484(5) 1 d P A 1 H10B H 0.4149 0.4180 -0.0248 0.042 Uiso 0.484(5) 1 calc PR A 1 C11B C 0.5808(10) 0.5086(10) -0.0869(6) 0.041(2) Uiso 0.484(5) 1 d P A 1 H11G H 0.6572 0.5052 -0.1262 0.049 Uiso 0.484(5) 1 calc PR A 1 H11H H 0.5696 0.5813 -0.0639 0.049 Uiso 0.484(5) 1 calc PR A 1 C9D C -0.3351(7) -0.0198(7) -0.2342(4) 0.0174(15) Uiso 0.484(5) 1 d P A 1 H9D1 H -0.3451 -0.0564 -0.2783 0.021 Uiso 0.484(5) 1 calc PR A 1 H9D2 H -0.2884 -0.0849 -0.1984 0.021 Uiso 0.484(5) 1 calc PR A 1 C10D C -0.4699(8) 0.0131(8) -0.1903(5) 0.0224(17) Uiso 0.484(5) 1 d P A 1 H10D H -0.5241 0.0733 -0.2195 0.027 Uiso 0.484(5) 1 calc PR A 1 C11D C -0.5169(9) -0.0379(9) -0.1127(5) 0.033(2) Uiso 0.484(5) 1 d P A 1 H11I H -0.4651 -0.0984 -0.0818 0.039 Uiso 0.484(5) 1 calc PR A 1 H11J H -0.6018 -0.0134 -0.0888 0.039 Uiso 0.484(5) 1 calc PR A 1 O2M O -0.6080(3) 0.1996(3) -0.49798(17) 0.0299(6) Uani 1 1 d . . . O1M O 0.0021(3) 0.8554(3) -0.27662(17) 0.0354(7) Uani 1 1 d . . . C2M C -0.0134(5) 0.8684(5) -0.3582(3) 0.0428(11) Uani 1 1 d . . . H2M1 H -0.0321 0.9610 -0.3827 0.064 Uiso 1 1 calc R . . H2M2 H -0.0870 0.8110 -0.3575 0.064 Uiso 1 1 calc R . . H2M3 H 0.0688 0.8420 -0.3884 0.064 Uiso 1 1 calc R . . C1M C -0.6757(6) 0.0878(5) -0.5060(3) 0.0596(16) Uani 1 1 d . . . H1M1 H -0.6654 0.0095 -0.4634 0.089 Uiso 1 1 calc R . . H1M2 H -0.6377 0.0704 -0.5569 0.089 Uiso 1 1 calc R . . H1M3 H -0.7703 0.1071 -0.5031 0.089 Uiso 1 1 calc R . . H2O2 H -0.5946 0.1878 -0.4506 0.19(5) Uiso 1 1 d R . . H2O1 H 0.0486 0.9229 -0.2773 0.09(2) Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C2 0.0136(15) 0.0171(16) 0.0235(17) -0.0086(14) -0.0024(14) -0.0022(13) C2A 0.0166(16) 0.0245(17) 0.0148(16) -0.0067(13) -0.0016(13) 0.0023(14) C2B 0.0210(17) 0.0132(15) 0.0225(17) -0.0078(13) -0.0069(14) 0.0027(13) C4 0.0120(15) 0.0217(17) 0.0209(17) -0.0115(14) -0.0030(13) 0.0002(13) C4A 0.0141(17) 0.044(2) 0.0178(17) -0.0057(16) -0.0007(14) -0.0031(16) C4B 0.0228(18) 0.0252(18) 0.0171(17) -0.0034(14) -0.0027(14) -0.0093(15) C5 0.0155(16) 0.0178(16) 0.0156(16) -0.0063(13) -0.0033(13) 0.0009(13) C5A 0.0151(16) 0.0172(16) 0.0190(17) -0.0061(13) -0.0043(13) 0.0021(13) C5B 0.0161(16) 0.0165(15) 0.0171(16) -0.0065(13) -0.0033(13) -0.0029(13) C6 0.0142(15) 0.0175(16) 0.0174(16) -0.0063(13) -0.0063(13) 0.0004(13) C6A 0.0169(16) 0.0153(15) 0.0168(16) -0.0072(13) -0.0052(13) 0.0028(12) C6B 0.0220(18) 0.0282(19) 0.0179(17) -0.0079(14) -0.0025(14) -0.0080(15) C8 0.0188(16) 0.0212(17) 0.0141(16) -0.0026(13) 0.0013(14) -0.0015(14) C8A 0.0149(17) 0.052(2) 0.0130(16) -0.0032(16) 0.0000(14) -0.0047(16) C8B 0.046(2) 0.042(2) 0.0177(18) 0.0040(17) -0.0136(18) -0.026(2) C9 0.036(2) 0.041(2) 0.0189(19) -0.0183(17) -0.0001(16) 0.0119(18) C10 0.039(2) 0.047(3) 0.025(2) -0.0098(19) 0.0056(18) 0.016(2) C11 0.077(4) 0.048(3) 0.025(2) -0.013(2) 0.005(2) 0.004(3) N1 0.0216(15) 0.0157(14) 0.0147(14) -0.0046(11) 0.0000(12) 0.0021(11) N1A 0.0155(14) 0.0182(14) 0.0119(13) -0.0039(11) -0.0014(11) -0.0009(11) N1B 0.0245(15) 0.0264(15) 0.0124(13) -0.0043(12) -0.0023(12) -0.0076(13) N2 0.0354(18) 0.0188(15) 0.0249(16) -0.0072(13) 0.0018(14) 0.0013(13) N2A 0.0170(14) 0.0294(16) 0.0182(14) -0.0065(12) -0.0034(12) -0.0032(12) N2B 0.0245(15) 0.0237(15) 0.0179(14) -0.0060(12) -0.0069(12) -0.0024(12) N3 0.0173(14) 0.0201(14) 0.0211(15) -0.0104(12) -0.0021(12) 0.0017(12) N3A 0.0176(15) 0.049(2) 0.0130(14) -0.0060(14) -0.0022(12) -0.0044(14) N3B 0.0256(16) 0.0379(18) 0.0191(16) -0.0041(13) -0.0070(13) -0.0132(14) N7 0.0174(14) 0.0220(15) 0.0127(13) -0.0050(11) 0.0004(11) 0.0002(12) N7A 0.0148(13) 0.0217(14) 0.0112(13) -0.0031(11) -0.0019(11) 0.0037(11) N7B 0.0172(14) 0.0166(13) 0.0140(13) -0.0041(11) -0.0011(11) -0.0019(11) N9 0.0201(15) 0.0238(15) 0.0145(14) -0.0088(12) 0.0016(12) 0.0029(12) N9A 0.0166(16) 0.082(3) 0.0123(15) -0.0006(16) -0.0042(13) -0.0128(17) N9B 0.052(2) 0.077(3) 0.0180(17) 0.0116(18) -0.0147(17) -0.048(2) O6 0.0157(11) 0.0175(11) 0.0160(11) -0.0078(9) -0.0008(9) -0.0012(9) O6A 0.0183(12) 0.0232(12) 0.0148(11) -0.0059(10) -0.0031(10) -0.0033(10) O6B 0.0257(14) 0.064(2) 0.0177(13) -0.0099(13) 0.0000(11) -0.0226(14) Cl1 0.0263(5) 0.0189(4) 0.0236(4) -0.0078(3) 0.0016(4) 0.0013(3) Cl2 0.0184(4) 0.0182(4) 0.0151(4) -0.0042(3) -0.0034(3) 0.0002(3) Cl3 0.0194(4) 0.0189(4) 0.0203(4) -0.0068(3) -0.0028(3) -0.0003(3) Cu1 0.0154(2) 0.0170(2) 0.0141(2) -0.00552(17) -0.00237(17) -0.00071(16) Cu2 0.0163(3) 0.0141(3) 0.0145(3) -0.0050(2) -0.0008(2) 0.0003(2) O2M 0.0353(15) 0.0296(14) 0.0260(14) -0.0095(11) -0.0038(12) -0.0098(12) O1M 0.0444(17) 0.0341(16) 0.0295(15) -0.0107(12) -0.0063(13) -0.0107(14) C2M 0.059(3) 0.038(2) 0.032(2) -0.011(2) -0.011(2) 0.002(2) C1M 0.078(4) 0.042(3) 0.056(3) -0.025(2) 0.014(3) -0.030(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 C2 N3 1.327(5) . ? C2 N2 1.340(5) . ? C2 N1 1.385(4) . ? C2A N3A 1.322(4) . ? C2A N2A 1.338(4) . ? C2A N1A 1.376(4) . ? C2B N3B 1.303(5) . ? C2B N2B 1.360(4) . ? C2B N1B 1.377(4) . ? C4 N3 1.348(4) . ? C4 N9 1.373(4) . ? C4 C5 1.381(5) . ? C4A N3A 1.352(5) . ? C4A N9A 1.366(5) . ? C4A C5A 1.380(5) . ? C4B N3B 1.347(5) . ? C4B N9B 1.369(5) . ? C4B C5B 1.382(5) . ? C5 N7 1.376(4) . ? C5 C6 1.407(5) . ? C5A N7A 1.372(4) . ? C5A C6A 1.418(5) . ? C5B N7B 1.385(4) . ? C5B C6B 1.408(5) . ? C6 O6 1.245(4) . ? C6 N1 1.389(4) . ? C6A O6A 1.233(4) . ? C6A N1A 1.396(4) . ? C6B O6B 1.222(4) . ? C6B N1B 1.400(4) . ? C8 N7 1.321(4) . ? C8 N9 1.375(4) . ? C8A N7A 1.320(4) . ? C8A N9A 1.367(5) . ? C8B N7B 1.305(5) . ? C8B N9B 1.361(5) . ? C9 C10 1.472(6) . ? C9 N9 1.474(4) . ? C10 C11 1.313(6) . ? N7 Cu2 1.982(3) . ? N7A Cu1 1.984(3) . ? N7B Cu1 1.979(3) . ? N9A C9B 1.489(7) . ? N9A C9A 1.549(8) . ? N9B C9D 1.532(8) . ? N9B C9C 1.579(8) . ? O6 Cu1 2.324(2) . ? Cl1 Cu1 2.2976(9) . ? Cl2 Cu1 2.3925(9) . ? Cl3 Cu2 2.2868(8) . ? Cu2 N7 1.982(3) 2 ? Cu2 Cl3 2.2868(8) 2 ? C9A C10A 1.478(10) . ? C10A C11A 1.315(11) . ? C9C C10C 1.473(11) . ? C10C C11C 1.332(11) . ? C9B C10B 1.496(12) . ? C10B C11B 1.294(13) . ? C9D C10D 1.494(10) . ? C10D C11D 1.320(12) . ? O2M C1M 1.406(5) . ? O1M C2M 1.447(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N3 C2 N2 119.3(3) . . ? N3 C2 N1 123.7(3) . . ? N2 C2 N1 117.0(3) . . ? N3A C2A N2A 118.6(3) . . ? N3A C2A N1A 123.4(3) . . ? N2A C2A N1A 118.0(3) . . ? N3B C2B N2B 120.0(3) . . ? N3B C2B N1B 123.8(3) . . ? N2B C2B N1B 116.1(3) . . ? N3 C4 N9 126.6(3) . . ? N3 C4 C5 127.7(3) . . ? N9 C4 C5 105.6(3) . . ? N3A C4A N9A 125.6(3) . . ? N3A C4A C5A 128.5(3) . . ? N9A C4A C5A 106.0(3) . . ? N3B C4B N9B 126.4(3) . . ? N3B C4B C5B 127.9(3) . . ? N9B C4B C5B 105.8(3) . . ? N7 C5 C4 110.3(3) . . ? N7 C5 C6 129.6(3) . . ? C4 C5 C6 120.0(3) . . ? N7A C5A C4A 109.3(3) . . ? N7A C5A C6A 131.6(3) . . ? C4A C5A C6A 119.1(3) . . ? C4B C5B N7B 109.2(3) . . ? C4B C5B C6B 119.6(3) . . ? N7B C5B C6B 131.1(3) . . ? O6 C6 N1 122.4(3) . . ? O6 C6 C5 126.1(3) . . ? N1 C6 C5 111.5(3) . . ? O6A C6A N1A 120.9(3) . . ? O6A C6A C5A 128.0(3) . . ? N1A C6A C5A 111.1(3) . . ? O6B C6B N1B 121.9(3) . . ? O6B C6B C5B 127.5(3) . . ? N1B C6B C5B 110.6(3) . . ? N7 C8 N9 111.5(3) . . ? N7A C8A N9A 110.7(3) . . ? N7B C8B N9B 111.9(3) . . ? C10 C9 N9 114.0(3) . . ? C11 C10 C9 125.1(5) . . ? C2 N1 C6 124.8(3) . . ? C2A N1A C6A 125.5(3) . . ? C2B N1B C6B 125.2(3) . . ? C2 N3 C4 112.3(3) . . ? C2A N3A C4A 112.3(3) . . ? C2B N3B C4B 112.6(3) . . ? C8 N7 C5 105.5(3) . . ? C8 N7 Cu2 135.9(2) . . ? C5 N7 Cu2 117.4(2) . . ? C8A N7A C5A 106.5(3) . . ? C8A N7A Cu1 125.8(2) . . ? C5A N7A Cu1 127.7(2) . . ? C8B N7B C5B 105.9(3) . . ? C8B N7B Cu1 127.7(2) . . ? C5B N7B Cu1 126.2(2) . . ? C4 N9 C8 107.0(3) . . ? C4 N9 C9 126.3(3) . . ? C8 N9 C9 126.0(3) . . ? C4A N9A C8A 107.5(3) . . ? C4A N9A C9B 126.8(4) . . ? C8A N9A C9B 123.1(4) . . ? C4A N9A C9A 123.9(4) . . ? C8A N9A C9A 124.4(4) . . ? C9B N9A C9A 32.7(3) . . ? C8B N9B C4B 107.2(3) . . ? C8B N9B C9D 121.2(4) . . ? C4B N9B C9D 121.9(4) . . ? C8B N9B C9C 127.0(4) . . ? C4B N9B C9C 120.9(4) . . ? C9D N9B C9C 47.9(4) . . ? C6 O6 Cu1 134.6(2) . . ? N7B Cu1 N7A 172.21(11) . . ? N7B Cu1 Cl1 90.62(8) . . ? N7A Cu1 Cl1 89.18(8) . . ? N7B Cu1 O6 85.63(10) . . ? N7A Cu1 O6 87.25(10) . . ? Cl1 Cu1 O6 112.44(6) . . ? N7B Cu1 Cl2 93.56(8) . . ? N7A Cu1 Cl2 90.31(8) . . ? Cl1 Cu1 Cl2 151.48(3) . . ? O6 Cu1 Cl2 96.01(6) . . ? N7 Cu2 N7 180.0(2) . 2 ? N7 Cu2 Cl3 88.74(8) . 2 ? N7 Cu2 Cl3 91.26(8) 2 2 ? N7 Cu2 Cl3 91.26(8) . . ? N7 Cu2 Cl3 88.74(8) 2 . ? Cl3 Cu2 Cl3 180.00(5) 2 . ? C10A C9A N9A 106.8(6) . . ? C11A C10A C9A 123.2(7) . . ? C10C C9C N9B 104.6(6) . . ? C11C C10C C9C 125.5(8) . . ? N9A C9B C10B 102.3(6) . . ? C11B C10B C9B 123.5(9) . . ? C10D C9D N9B 104.2(5) . . ? C11D C10D C9D 124.1(7) . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 1.281 _refine_diff_density_min -0.906 _refine_diff_density_rms 0.225 _database_code_depnum_ccdc_archive 'CCDC 808673'