# 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_s222 #TrackingRef 'web_deposit_cif_file_0_FERLAY_1361195420.A(222).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H10 N2, C2 Cu N2' _chemical_formula_sum 'C9 H10 Cu N4' _chemical_formula_weight 237.75 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.3350(3) _cell_length_b 7.7340(2) _cell_length_c 11.4860(3) _cell_angle_alpha 90.00 _cell_angle_beta 117.5791(13) _cell_angle_gamma 90.00 _cell_volume 971.24(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3046 _cell_measurement_theta_min 1.018 _cell_measurement_theta_max 30.999 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.626 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 484 _exptl_absorpt_coefficient_mu 2.211 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7327 _exptl_absorpt_correction_T_max 0.7930 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_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 5222 _diffrn_reflns_av_R_equivalents 0.0201 _diffrn_reflns_av_sigmaI/netI 0.0453 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.23 _diffrn_reflns_theta_max 31.02 _reflns_number_total 3092 _reflns_number_gt 2508 _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^)+(0.0374P)^2^+0.2848P] 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 3092 _refine_ls_number_parameters 127 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0454 _refine_ls_R_factor_gt 0.0330 _refine_ls_wR_factor_ref 0.0898 _refine_ls_wR_factor_gt 0.0843 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _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 C1 C 0.33973(14) 0.7381(2) 0.03876(14) 0.0213(3) Uani 1 1 d . . . N1 N 0.22312(12) 0.7009(2) -0.00606(13) 0.0248(3) Uani 1 1 d . . . H2 H 0.1934 0.6112 -0.0585 0.030 Uiso 1 1 calc . . . C2 C 0.13984(16) 0.8013(3) 0.02677(17) 0.0299(4) Uani 1 1 d . . . H10A H 0.0856 0.7219 0.0434 0.036 Uiso 1 1 calc . . . H10B H 0.0881 0.8771 -0.0479 0.036 Uiso 1 1 calc . . . C3 C 0.21327(18) 0.9103(3) 0.14793(18) 0.0317(4) Uani 1 1 d . . . H2A H 0.1587 0.9939 0.1603 0.038 Uiso 1 1 calc . . . H2B H 0.2506 0.8351 0.2265 0.038 Uiso 1 1 calc . . . C4 C 0.31232(16) 1.0063(2) 0.13192(17) 0.0303(4) Uani 1 1 d . . . H12A H 0.2751 1.0896 0.0584 0.036 Uiso 1 1 calc . . . H12B H 0.3642 1.0714 0.2131 0.036 Uiso 1 1 calc . . . N2 N 0.38700(13) 0.88037(18) 0.10507(14) 0.0244(3) Uani 1 1 d . . . H3 H 0.4655 0.9009 0.1342 0.029 Uiso 1 1 calc . . . C5 C 0.42101(15) 0.6149(2) 0.01641(15) 0.0215(3) Uani 1 1 d . . . C6 C 0.40671(15) 0.4377(2) 0.02403(16) 0.0241(3) Uani 1 1 d . . . H13 H 0.3426 0.3951 0.0400 0.029 Uiso 1 1 calc . . . C7 C 0.51471(15) 0.6777(2) -0.00844(16) 0.0235(3) Uani 1 1 d . . . H8 H 0.5245 0.7987 -0.0146 0.028 Uiso 1 1 calc . . . Cu1 Cu 0.115928(19) 0.38823(3) 0.25758(2) 0.02963(9) Uani 1 1 d . . . C8 C 0.26965(16) 0.4545(3) 0.27034(17) 0.0301(4) Uani 1 1 d . . . N3 N 0.36522(14) 0.4873(2) 0.28275(15) 0.0346(4) Uani 1 1 d . . . N4 N -0.01993(15) 0.5622(2) 0.17239(16) 0.0331(3) Uani 1 1 d . . . C9 C -0.06062(16) 0.6892(2) 0.18745(17) 0.0296(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0228(7) 0.0221(7) 0.0195(6) 0.0005(5) 0.0104(6) 0.0000(6) N1 0.0219(6) 0.0284(7) 0.0242(6) -0.0037(5) 0.0108(5) -0.0015(6) C2 0.0225(8) 0.0368(10) 0.0327(8) -0.0030(7) 0.0148(7) 0.0016(7) C3 0.0312(9) 0.0370(10) 0.0298(8) -0.0029(7) 0.0167(7) 0.0043(7) C4 0.0289(9) 0.0257(8) 0.0356(9) -0.0062(7) 0.0143(7) 0.0030(7) N2 0.0209(7) 0.0242(7) 0.0282(7) -0.0050(5) 0.0114(6) -0.0009(5) C5 0.0235(8) 0.0220(7) 0.0196(7) -0.0022(5) 0.0105(6) -0.0007(6) C6 0.0256(8) 0.0240(8) 0.0271(7) -0.0032(6) 0.0159(7) -0.0038(6) C7 0.0279(8) 0.0193(7) 0.0262(7) -0.0017(6) 0.0150(6) -0.0023(6) Cu1 0.02713(14) 0.02838(13) 0.03606(14) -0.00225(9) 0.01691(11) -0.00240(8) C8 0.0300(9) 0.0306(9) 0.0307(8) 0.0043(7) 0.0149(7) 0.0034(7) N3 0.0267(8) 0.0420(10) 0.0347(8) 0.0067(7) 0.0138(6) 0.0034(7) N4 0.0304(8) 0.0308(8) 0.0397(8) 0.0004(7) 0.0175(7) -0.0008(6) C9 0.0256(8) 0.0310(9) 0.0325(8) -0.0001(7) 0.0137(7) -0.0021(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N2 1.311(2) . ? C1 N1 1.316(2) . ? C1 C5 1.489(2) . ? N1 C2 1.469(2) . ? N1 H2 0.8800 . ? C2 C3 1.517(3) . ? C2 H10A 0.9900 . ? C2 H10B 0.9900 . ? C3 C4 1.512(3) . ? C3 H2A 0.9900 . ? C3 H2B 0.9900 . ? C4 N2 1.468(2) . ? C4 H12A 0.9900 . ? C4 H12B 0.9900 . ? N2 H3 0.8800 . ? C5 C6 1.390(2) . ? C5 C7 1.400(2) . ? C6 C7 1.389(2) 3_665 ? C6 H13 0.9500 . ? C7 C6 1.389(2) 3_665 ? C7 H8 0.9500 . ? Cu1 C8 1.9033(18) . ? Cu1 C9 1.9056(19) 2_545 ? Cu1 N4 2.0143(17) . ? C8 N3 1.148(2) . ? N4 C9 1.152(3) . ? C9 Cu1 1.9056(19) 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 C1 N1 121.49(15) . . ? N2 C1 C5 118.89(14) . . ? N1 C1 C5 119.60(15) . . ? C1 N1 C2 123.48(15) . . ? C1 N1 H2 118.3 . . ? C2 N1 H2 118.3 . . ? N1 C2 C3 109.73(14) . . ? N1 C2 H10A 109.7 . . ? C3 C2 H10A 109.7 . . ? N1 C2 H10B 109.7 . . ? C3 C2 H10B 109.7 . . ? H10A C2 H10B 108.2 . . ? C4 C3 C2 109.53(14) . . ? C4 C3 H2A 109.8 . . ? C2 C3 H2A 109.8 . . ? C4 C3 H2B 109.8 . . ? C2 C3 H2B 109.8 . . ? H2A C3 H2B 108.2 . . ? N2 C4 C3 108.73(15) . . ? N2 C4 H12A 109.9 . . ? C3 C4 H12A 109.9 . . ? N2 C4 H12B 109.9 . . ? C3 C4 H12B 109.9 . . ? H12A C4 H12B 108.3 . . ? C1 N2 C4 121.67(14) . . ? C1 N2 H3 119.2 . . ? C4 N2 H3 119.2 . . ? C6 C5 C7 119.73(15) . . ? C6 C5 C1 120.33(14) . . ? C7 C5 C1 119.91(14) . . ? C7 C6 C5 120.61(15) 3_665 . ? C7 C6 H13 119.7 3_665 . ? C5 C6 H13 119.7 . . ? C6 C7 C5 119.65(15) 3_665 . ? C6 C7 H8 120.2 3_665 . ? C5 C7 H8 120.2 . . ? C8 Cu1 C9 133.53(8) . 2_545 ? C8 Cu1 N4 115.63(7) . . ? C9 Cu1 N4 110.82(7) 2_545 . ? N3 C8 Cu1 176.31(17) . . ? C9 N4 Cu1 144.97(15) . . ? N4 C9 Cu1 170.42(16) . 2 ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 31.02 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.347 _refine_diff_density_min -0.454 _refine_diff_density_rms 0.068 _database_code_depnum_ccdc_archive 'CCDC 924952' ####################################################################### # # 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_e522a #TrackingRef 'web_deposit_cif_file_1_FERLAY_1361195420.B(522).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H22 N2, C3 Cu2 N3, C H4 O' _chemical_formula_sum 'C17 H26 Cu2 N5 O' _chemical_formula_weight 443.51 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' 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' H H 0.0000 0.0000 '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_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.3378(7) _cell_length_b 8.4859(7) _cell_length_c 16.0299(15) _cell_angle_alpha 93.171(3) _cell_angle_beta 92.107(3) _cell_angle_gamma 115.690(2) _cell_volume 1018.17(15) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1617 _cell_measurement_theta_min 2.86 _cell_measurement_theta_max 26.69 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.447 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 458 _exptl_absorpt_coefficient_mu 2.102 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7297 _exptl_absorpt_correction_T_max 0.8173 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_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 11641 _diffrn_reflns_av_R_equivalents 0.0296 _diffrn_reflns_av_sigmaI/netI 0.0367 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.67 _diffrn_reflns_theta_max 27.53 _reflns_number_total 4633 _reflns_number_gt 3521 _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^)+(0.0431P)^2^+0.8169P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4633 _refine_ls_number_parameters 237 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0579 _refine_ls_R_factor_gt 0.0400 _refine_ls_wR_factor_ref 0.1045 _refine_ls_wR_factor_gt 0.0978 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.081 _refine_ls_shift/su_max 0.003 _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 C1 C 0.6603(3) 0.0820(3) 0.16840(15) 0.0232(5) Uani 1 1 d . . . N1 N 0.6118(3) -0.0406(3) 0.22077(13) 0.0288(5) Uani 1 1 d . . . H1 H 0.5252 -0.1444 0.2045 0.035 Uiso 1 1 calc R . . C2 C 0.6962(4) -0.0118(3) 0.30572(15) 0.0300(6) Uani 1 1 d . . . H2A H 0.8027 -0.0350 0.3046 0.036 Uiso 1 1 calc R . . H2B H 0.6117 -0.0938 0.3425 0.036 Uiso 1 1 calc R . . C3 C 0.7512(3) 0.1779(3) 0.34040(14) 0.0225(5) Uani 1 1 d . . . C4 C 0.8668(3) 0.2969(3) 0.27606(14) 0.0261(5) Uani 1 1 d . . . H4A H 0.8876 0.4193 0.2909 0.031 Uiso 1 1 calc R . . H4B H 0.9841 0.2935 0.2777 0.031 Uiso 1 1 calc R . . N2 N 0.7809(3) 0.2412(3) 0.19092(12) 0.0270(5) Uani 1 1 d . . . H2 H 0.8123 0.3189 0.1532 0.032 Uiso 1 1 calc R . . C5 C 0.8716(3) 0.2168(4) 0.42149(15) 0.0286(5) Uani 1 1 d . . . H5A H 0.9732 0.1905 0.4089 0.034 Uiso 1 1 calc R . . H5B H 0.9210 0.3439 0.4382 0.034 Uiso 1 1 calc R . . C6 C 0.7829(4) 0.1164(4) 0.49619(16) 0.0398(7) Uani 1 1 d . . . H6A H 0.7324 -0.0112 0.4804 0.048 Uiso 1 1 calc R . . H6B H 0.6835 0.1447 0.5109 0.048 Uiso 1 1 calc R . . C7 C 0.9149(5) 0.1623(5) 0.57254(19) 0.0525(9) Uani 1 1 d . . . H7A H 1.0182 0.1435 0.5570 0.079 Uiso 1 1 calc R . . H7B H 0.8567 0.0872 0.6171 0.079 Uiso 1 1 calc R . . H7C H 0.9543 0.2855 0.5924 0.079 Uiso 1 1 calc R . . C8 C 0.5821(3) 0.2052(4) 0.35319(16) 0.0316(6) Uani 1 1 d . . . H8A H 0.5148 0.1823 0.2982 0.038 Uiso 1 1 calc R . . H8B H 0.5061 0.1160 0.3898 0.038 Uiso 1 1 calc R . . C9 C 0.6104(4) 0.3843(5) 0.39067(19) 0.0445(8) Uani 1 1 d . . . H9A H 0.6834 0.4754 0.3541 0.053 Uiso 1 1 calc R . . H9B H 0.6761 0.4092 0.4462 0.053 Uiso 1 1 calc R . . C10 C 0.4315(6) 0.3914(7) 0.4001(2) 0.0691(13) Uani 1 1 d . . . H10A H 0.3605 0.3530 0.3465 0.104 Uiso 1 1 calc R . . H10B H 0.4527 0.5119 0.4171 0.104 Uiso 1 1 calc R . . H10C H 0.3668 0.3138 0.4427 0.104 Uiso 1 1 calc R . . C11 C 0.5762(3) 0.0395(3) 0.08135(15) 0.0246(5) Uani 1 1 d . . . C12 C 0.5374(4) -0.1228(3) 0.04015(16) 0.0300(6) Uani 1 1 d . . . H12 H 0.5630 -0.2064 0.0677 0.036 Uiso 1 1 calc R . . C13 C 0.5391(4) 0.1627(3) 0.04146(16) 0.0291(5) Uani 1 1 d . . . H13 H 0.5659 0.2734 0.0698 0.035 Uiso 1 1 calc R . . Cu1 Cu -0.03657(5) 0.19728(5) 0.80229(3) 0.04961(14) Uani 1 1 d . . . Cu2 Cu 0.61927(5) 0.55347(5) 0.80928(2) 0.04484(13) Uani 1 1 d . . . C14 C 0.3682(4) 0.4282(4) 0.81519(18) 0.0406(6) Uani 0.50 1 d P . . N3 N 0.3682(4) 0.4282(4) 0.81519(18) 0.0406(6) Uani 0.50 1 d P . . C15 C 0.2158(4) 0.3389(4) 0.81018(19) 0.0424(7) Uani 0.50 1 d P . . N4 N 0.2158(4) 0.3389(4) 0.81018(19) 0.0424(7) Uani 0.50 1 d P . . C16 C -0.1508(4) -0.0508(4) 0.8073(2) 0.0452(7) Uani 0.50 1 d P . . N5 N -0.1508(4) -0.0508(4) 0.8073(2) 0.0452(7) Uani 0.50 1 d P . . C17 C -0.1820(4) 0.3209(4) 0.7935(2) 0.0538(8) Uani 0.50 1 d P . . N6 N -0.1820(4) 0.3209(4) 0.7935(2) 0.0538(8) Uani 0.50 1 d P . . C18 C 0.7637(4) 0.7991(4) 0.81225(19) 0.0426(6) Uani 0.50 1 d P . . N7 N 0.7637(4) 0.7991(4) 0.81225(19) 0.0426(6) Uani 0.50 1 d P . . C19 C 0.7368(4) 0.4020(4) 0.7952(2) 0.0502(8) Uani 0.50 1 d P . . N8 N 0.7368(4) 0.4020(4) 0.7952(2) 0.0502(8) Uani 0.50 1 d P . . C20 C 1.0242(7) 0.3230(8) 0.0389(4) 0.0872(15) Uani 1 1 d D . . O1A O 0.9796(11) 0.1590(14) 0.0002(6) 0.161(5) Uani 0.50 1 d PD . . O1 O 0.9342(8) 0.4180(8) 0.0509(3) 0.0739(18) Uani 0.50 1 d PD . . 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 C1 0.0275(12) 0.0223(12) 0.0226(11) 0.0023(9) 0.0051(9) 0.0131(10) N1 0.0367(12) 0.0206(11) 0.0237(10) -0.0001(8) -0.0032(9) 0.0080(9) C2 0.0378(14) 0.0263(14) 0.0236(12) 0.0053(10) -0.0010(10) 0.0117(11) C3 0.0228(11) 0.0229(12) 0.0202(11) 0.0014(9) 0.0007(9) 0.0087(9) C4 0.0249(12) 0.0262(13) 0.0220(12) 0.0033(10) 0.0019(9) 0.0061(10) N2 0.0320(11) 0.0254(11) 0.0200(10) 0.0054(8) 0.0032(8) 0.0086(9) C5 0.0267(12) 0.0316(14) 0.0237(12) 0.0022(10) -0.0015(10) 0.0096(11) C6 0.0411(16) 0.0484(18) 0.0229(13) 0.0091(12) -0.0011(11) 0.0126(13) C7 0.058(2) 0.061(2) 0.0285(15) 0.0090(15) -0.0076(14) 0.0171(17) C8 0.0270(13) 0.0460(17) 0.0239(12) 0.0010(11) 0.0027(10) 0.0180(12) C9 0.0554(19) 0.060(2) 0.0334(15) -0.0029(14) 0.0048(13) 0.0397(17) C10 0.084(3) 0.116(4) 0.0421(19) -0.017(2) -0.0064(18) 0.080(3) C11 0.0264(12) 0.0256(13) 0.0217(11) 0.0016(10) 0.0044(9) 0.0111(10) C12 0.0413(15) 0.0262(14) 0.0260(13) 0.0026(10) -0.0007(11) 0.0183(12) C13 0.0381(14) 0.0242(13) 0.0265(12) -0.0022(10) 0.0011(11) 0.0155(11) Cu1 0.0453(2) 0.0422(3) 0.0617(3) 0.00016(19) 0.00996(19) 0.01940(19) Cu2 0.0436(2) 0.0425(2) 0.0490(2) 0.00509(17) 0.00695(17) 0.01894(18) C14 0.0436(16) 0.0323(15) 0.0557(17) 0.0096(12) 0.0128(13) 0.0244(13) N3 0.0436(16) 0.0323(15) 0.0557(17) 0.0096(12) 0.0128(13) 0.0244(13) C15 0.0433(16) 0.0298(14) 0.0631(19) 0.0084(13) 0.0129(13) 0.0229(13) N4 0.0433(16) 0.0298(14) 0.0631(19) 0.0084(13) 0.0129(13) 0.0229(13) C16 0.0376(15) 0.0412(18) 0.0619(19) -0.0021(14) -0.0001(13) 0.0230(14) N5 0.0376(15) 0.0412(18) 0.0619(19) -0.0021(14) -0.0001(13) 0.0230(14) C17 0.0327(15) 0.0312(16) 0.090(2) 0.0117(15) 0.0172(15) 0.0049(13) N6 0.0327(15) 0.0312(16) 0.090(2) 0.0117(15) 0.0172(15) 0.0049(13) C18 0.0337(14) 0.0403(17) 0.0561(18) -0.0035(13) 0.0024(12) 0.0193(13) N7 0.0337(14) 0.0403(17) 0.0561(18) -0.0035(13) 0.0024(12) 0.0193(13) C19 0.0337(14) 0.0263(15) 0.091(2) 0.0103(14) 0.0181(14) 0.0117(12) N8 0.0337(14) 0.0263(15) 0.091(2) 0.0103(14) 0.0181(14) 0.0117(12) C20 0.064(3) 0.088(4) 0.097(4) -0.001(3) -0.018(3) 0.024(3) O1A 0.079(6) 0.286(16) 0.098(6) 0.025(8) 0.011(5) 0.059(8) O1 0.067(3) 0.075(4) 0.043(3) 0.014(3) 0.017(2) -0.005(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 C1 N2 1.307(3) . ? C1 N1 1.307(3) . ? C1 C11 1.491(3) . ? N1 C2 1.467(3) . ? N1 H1 0.8800 . ? C2 C3 1.534(4) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C5 1.541(3) . ? C3 C4 1.535(3) . ? C3 C8 1.543(3) . ? C4 N2 1.470(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? N2 H2 0.8800 . ? C5 C6 1.529(4) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.529(4) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C9 1.518(4) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.532(4) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C13 1.392(4) . ? C11 C12 1.391(4) . ? C12 C13 1.391(4) 2_655 ? C12 H12 0.9500 . ? C13 C12 1.391(4) 2_655 ? C13 H13 0.9500 . ? Cu1 C16 1.906(3) . ? Cu1 C15 1.913(3) . ? Cu1 C17 1.923(3) . ? Cu2 C14 1.902(3) . ? Cu2 C18 1.899(3) . ? Cu2 C19 1.933(3) . ? C14 C15 1.160(4) . ? C16 N7 1.168(4) 1_445 ? C16 C18 1.168(4) 1_445 ? C17 N8 1.156(4) 1_455 ? C17 C19 1.156(4) 1_455 ? C18 N5 1.168(4) 1_665 ? C18 C16 1.168(4) 1_665 ? C19 N6 1.156(4) 1_655 ? C19 C17 1.156(4) 1_655 ? C20 O1 1.330(7) . ? C20 O1A 1.378(8) . ? 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 C1 N1 121.3(2) . . ? N2 C1 C11 119.4(2) . . ? N1 C1 C11 119.3(2) . . ? C1 N1 C2 122.5(2) . . ? C1 N1 H1 118.8 . . ? C2 N1 H1 118.8 . . ? N1 C2 C3 109.9(2) . . ? N1 C2 H2A 109.7 . . ? C3 C2 H2A 109.7 . . ? N1 C2 H2B 109.7 . . ? C3 C2 H2B 109.7 . . ? H2A C2 H2B 108.2 . . ? C2 C3 C5 109.3(2) . . ? C2 C3 C4 106.75(19) . . ? C5 C3 C4 106.65(19) . . ? C2 C3 C8 109.2(2) . . ? C5 C3 C8 113.1(2) . . ? C4 C3 C8 111.7(2) . . ? N2 C4 C3 111.33(19) . . ? N2 C4 H4A 109.4 . . ? C3 C4 H4A 109.4 . . ? N2 C4 H4B 109.4 . . ? C3 C4 H4B 109.4 . . ? H4A C4 H4B 108.0 . . ? C1 N2 C4 123.3(2) . . ? C1 N2 H2 118.4 . . ? C4 N2 H2 118.4 . . ? C6 C5 C3 116.2(2) . . ? C6 C5 H5A 108.2 . . ? C3 C5 H5A 108.2 . . ? C6 C5 H5B 108.2 . . ? C3 C5 H5B 108.2 . . ? H5A C5 H5B 107.4 . . ? C5 C6 C7 111.8(2) . . ? C5 C6 H6A 109.3 . . ? C7 C6 H6A 109.3 . . ? C5 C6 H6B 109.3 . . ? C7 C6 H6B 109.3 . . ? H6A C6 H6B 107.9 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C9 C8 C3 116.7(2) . . ? C9 C8 H8A 108.1 . . ? C3 C8 H8A 108.1 . . ? C9 C8 H8B 108.1 . . ? C3 C8 H8B 108.1 . . ? H8A C8 H8B 107.3 . . ? C8 C9 C10 110.7(3) . . ? C8 C9 H9A 109.5 . . ? C10 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? C10 C9 H9B 109.5 . . ? H9A C9 H9B 108.1 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C13 C11 C12 120.4(2) . . ? C13 C11 C1 120.0(2) . . ? C12 C11 C1 119.6(2) . . ? C11 C12 C13 119.9(2) . 2_655 ? C11 C12 H12 120.0 . . ? C13 C12 H12 120.0 2_655 . ? C11 C13 C12 119.6(2) . 2_655 ? C11 C13 H13 120.2 . . ? C12 C13 H13 120.2 2_655 . ? C16 Cu1 C15 125.19(11) . . ? C16 Cu1 C17 118.71(12) . . ? C15 Cu1 C17 116.04(11) . . ? C14 Cu2 C18 129.45(11) . . ? C14 Cu2 C19 113.19(12) . . ? C18 Cu2 C19 117.33(12) . . ? C15 C14 Cu2 171.4(3) . . ? C14 C15 Cu1 178.5(3) . . ? N7 C16 Cu1 173.1(3) 1_445 . ? C18 C16 Cu1 173.1(3) 1_445 . ? N8 C17 Cu1 174.0(4) 1_455 . ? C19 C17 Cu1 174.0(4) 1_455 . ? N5 C18 Cu2 174.6(3) 1_665 . ? C16 C18 Cu2 174.6(3) 1_665 . ? N6 C19 Cu2 173.3(3) 1_655 . ? C17 C19 Cu2 173.3(3) 1_655 . ? O1 C20 O1A 133.3(6) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.779 _refine_diff_density_min -0.585 _refine_diff_density_rms 0.070 _database_code_depnum_ccdc_archive 'CCDC 924953' ####################################################################### # # 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_e900a #TrackingRef 'web_deposit_cif_file_2_FERLAY_1361195420.C(900).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C4 Cu3 N4, C7 H10 N2 O' _chemical_formula_sum 'C11 H10 Cu3 N6 O' _chemical_formula_weight 432.87 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' 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_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.5782(15) _cell_length_b 9.0487(16) _cell_length_c 9.1472(16) _cell_angle_alpha 96.855(4) _cell_angle_beta 92.638(3) _cell_angle_gamma 105.014(4) _cell_volume 678.7(2) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 965 _cell_measurement_theta_min 2.92 _cell_measurement_theta_max 27.22 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.04 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 2.118 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 426 _exptl_absorpt_coefficient_mu 4.663 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8354 _exptl_absorpt_correction_T_max 0.9125 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_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 4934 _diffrn_reflns_av_R_equivalents 0.0388 _diffrn_reflns_av_sigmaI/netI 0.0959 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 28.59 _reflns_number_total 3413 _reflns_number_gt 1923 _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^)+(0.0000P)^2^+27.9937P] 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 SHELXL _refine_ls_extinction_coef 0.0021(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3413 _refine_ls_number_parameters 168 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1613 _refine_ls_R_factor_gt 0.1009 _refine_ls_wR_factor_ref 0.2909 _refine_ls_wR_factor_gt 0.2637 _refine_ls_goodness_of_fit_ref 1.244 _refine_ls_restrained_S_all 1.244 _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 Cu3 Cu -0.1961(3) -0.3839(2) 0.5565(2) 0.0363(6) Uani 1 1 d . . . C1 C 0.6742(16) 0.1125(17) 0.2610(16) 0.0252(19) Uani 1 1 d . . . N1 N 0.6640(14) 0.0208(14) 0.1368(13) 0.0252(19) Uani 1 1 d . . . H1A H 0.6024 -0.0745 0.1293 0.030 Uiso 1 1 calc R . . C2 C 0.7517(18) 0.0710(17) 0.0095(17) 0.029(3) Uani 1 1 d . . . H2A H 0.6945 0.0085 -0.0830 0.034 Uiso 1 1 calc R . . H2B H 0.8623 0.0570 0.0186 0.034 Uiso 1 1 calc R . . C3 C 0.7603(17) 0.2387(18) 0.0060(18) 0.030(3) Uani 1 1 d . . . H3 H 0.8261 0.2768 -0.0760 0.036 Uiso 1 1 calc R . . O1 O 0.5980(12) 0.2490(13) -0.0215(13) 0.033(2) Uani 1 1 d . . . H1 H 0.5998 0.3389 -0.0375 0.049 Uiso 1 1 calc R . . C4 C 0.8397(18) 0.3313(18) 0.1525(16) 0.029(3) Uani 1 1 d . . . H4A H 0.9566 0.3367 0.1599 0.035 Uiso 1 1 calc R . . H4B H 0.8283 0.4379 0.1585 0.035 Uiso 1 1 calc R . . N2 N 0.7619(13) 0.2565(14) 0.2738(14) 0.026(3) Uani 1 1 d . . . H2 H 0.7749 0.3120 0.3615 0.031 Uiso 1 1 calc R . . C5 C 0.5861(15) 0.0546(16) 0.3844(16) 0.022(3) Uani 1 1 d . . . C6 C 0.5699(19) -0.0962(17) 0.4121(17) 0.029(3) Uani 1 1 d . . . H6 H 0.6175 -0.1622 0.3512 0.035 Uiso 1 1 calc R . . C7 C 0.5150(16) 0.1500(17) 0.4721(15) 0.025(3) Uani 1 1 d . . . H7 H 0.5247 0.2527 0.4525 0.030 Uiso 1 1 calc R . . Cu1 Cu -0.0104(3) 0.1781(2) 0.7181(2) 0.0353(5) Uani 1 1 d . . . Cu2 Cu 0.3559(3) 0.4034(3) 1.1700(3) 0.0420(6) Uani 1 1 d . . . N3 N -0.0808(19) -0.0435(18) 0.6751(17) 0.036(3) Uani 0.50 1 d P . . C8 C -0.0808(19) -0.0435(18) 0.6751(17) 0.036(3) Uani 0.50 1 d P . . N4 N -0.093(2) 0.3353(18) 0.6465(18) 0.039 Uani 0.50 1 d P . . C9 C -0.093(2) 0.3353(18) 0.6465(18) 0.039 Uani 0.50 1 d P . . N5 N 0.1424(17) 0.2581(17) 0.8914(17) 0.033(3) Uani 0.50 1 d P . . C10 C 0.1424(17) 0.2581(17) 0.8914(17) 0.033(3) Uani 0.50 1 d P . . N6 N 0.221(2) 0.3174(18) 1.0019(18) 0.039 Uani 0.50 1 d P . . C11 C 0.221(2) 0.3174(18) 1.0019(18) 0.039 Uani 0.50 1 d P . . N7 N 0.5298(18) 0.4995(17) 1.2986(17) 0.034(3) Uani 0.50 1 d P . . C12 C 0.5298(18) 0.4995(17) 1.2986(17) 0.034(3) Uani 0.50 1 d P . . N8 N -0.128(2) -0.174(2) 0.6409(19) 0.046(4) Uani 0.50 1 d P . . C13 C -0.128(2) -0.174(2) 0.6409(19) 0.046(4) Uani 0.50 1 d P . . N9 N -0.353(2) -0.4462(18) 0.3857(18) 0.039 Uani 0.50 1 d P . . C14 C -0.353(2) -0.4462(18) 0.3857(18) 0.039 Uani 0.50 1 d P . . N10 N -0.1392(16) -0.5626(16) 0.6137(16) 0.031(3) Uani 0.50 1 d P . . C15 C -0.1392(16) -0.5626(16) 0.6137(16) 0.031(3) Uani 0.50 1 d P . . 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 Cu3 0.0300(10) 0.0351(11) 0.0411(12) 0.0013(9) -0.0050(9) 0.0068(8) C1 0.017(4) 0.029(5) 0.027(5) 0.002(4) 0.001(4) 0.003(4) N1 0.017(4) 0.029(5) 0.027(5) 0.002(4) 0.001(4) 0.003(4) C2 0.028(7) 0.029(7) 0.027(8) 0.006(6) 0.009(6) 0.003(6) C3 0.018(7) 0.036(8) 0.035(8) 0.005(7) -0.003(6) 0.006(6) O1 0.027(5) 0.031(6) 0.039(6) 0.012(5) -0.007(5) 0.004(5) C4 0.023(7) 0.033(8) 0.027(8) 0.007(6) 0.001(6) 0.001(6) N2 0.012(5) 0.029(6) 0.031(7) 0.002(5) -0.002(5) -0.004(5) C5 0.013(6) 0.022(6) 0.028(7) 0.001(5) -0.002(5) 0.002(5) C6 0.033(8) 0.025(7) 0.033(8) 0.009(6) 0.005(7) 0.009(6) C7 0.017(6) 0.030(7) 0.022(7) 0.000(6) -0.008(5) 0.000(6) Cu1 0.0334(11) 0.0348(11) 0.0371(12) 0.0045(9) 0.0025(9) 0.0080(9) Cu2 0.0350(12) 0.0455(13) 0.0407(13) 0.0028(10) -0.0134(9) 0.0061(10) N3 0.039(8) 0.033(8) 0.033(8) 0.004(6) -0.008(7) 0.008(7) C8 0.039(8) 0.033(8) 0.033(8) 0.004(6) -0.008(7) 0.008(7) N4 0.045 0.034 0.043 0.014 0.020 0.013 C9 0.045 0.034 0.043 0.014 0.020 0.013 N5 0.023(7) 0.039(8) 0.040(8) 0.010(7) 0.003(6) 0.009(6) C10 0.023(7) 0.039(8) 0.040(8) 0.010(7) 0.003(6) 0.009(6) N6 0.045 0.034 0.043 0.014 0.020 0.013 C11 0.045 0.034 0.043 0.014 0.020 0.013 N7 0.029(7) 0.037(8) 0.038(8) 0.007(7) 0.007(6) 0.007(6) C12 0.029(7) 0.037(8) 0.038(8) 0.007(7) 0.007(6) 0.007(6) N8 0.049(10) 0.049(10) 0.042(10) 0.000(8) -0.011(8) 0.023(8) C13 0.049(10) 0.049(10) 0.042(10) 0.000(8) -0.011(8) 0.023(8) N9 0.045 0.034 0.043 0.014 0.020 0.013 C14 0.045 0.034 0.043 0.014 0.020 0.013 N10 0.026(7) 0.031(7) 0.031(7) 0.002(6) -0.010(6) 0.003(6) C15 0.026(7) 0.031(7) 0.031(7) 0.002(6) -0.010(6) 0.003(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu3 N8 1.894(18) . ? Cu3 N10 1.927(14) . ? Cu3 N9 1.944(18) . ? Cu3 Cu2 2.909(3) 2_557 ? C1 N1 1.309(18) . ? C1 N2 1.314(18) . ? C1 C5 1.462(19) . ? N1 C2 1.469(17) . ? N1 H1A 0.8800 . ? C2 C3 1.50(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 O1 1.432(17) . ? C3 C4 1.52(2) . ? C3 H3 1.0000 . ? O1 H1 0.8400 . ? C4 N2 1.466(18) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? N2 H2 0.8800 . ? C5 C7 1.383(19) . ? C5 C6 1.390(19) . ? C6 C7 1.38(2) 2_656 ? C6 H6 0.9500 . ? C7 C6 1.38(2) 2_656 ? C7 H7 0.9500 . ? Cu1 N4 1.913(16) . ? Cu1 N3 1.925(16) . ? Cu1 N5 1.949(15) . ? Cu2 N7 1.813(16) . ? Cu2 N6 1.841(18) . ? Cu2 Cu3 2.909(3) 2_557 ? N3 N8 1.14(2) . ? N4 C15 1.158(19) 1_565 ? N4 N10 1.158(19) 1_565 ? N5 N6 1.18(2) . ? N7 C14 1.21(2) 1_666 ? N7 N9 1.21(2) 1_666 ? N9 C12 1.21(2) 1_444 ? N9 N7 1.21(2) 1_444 ? N10 C9 1.158(19) 1_545 ? N10 N4 1.158(19) 1_545 ? 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 N8 Cu3 N10 130.7(6) . . ? N8 Cu3 N9 119.6(7) . . ? N10 Cu3 N9 109.6(6) . . ? N8 Cu3 Cu2 80.3(6) . 2_557 ? N10 Cu3 Cu2 81.4(5) . 2_557 ? N9 Cu3 Cu2 111.0(4) . 2_557 ? N1 C1 N2 120.1(13) . . ? N1 C1 C5 119.8(13) . . ? N2 C1 C5 120.2(13) . . ? C1 N1 C2 122.5(12) . . ? C1 N1 H1A 118.8 . . ? C2 N1 H1A 118.8 . . ? N1 C2 C3 108.4(12) . . ? N1 C2 H2A 110.0 . . ? C3 C2 H2A 110.0 . . ? N1 C2 H2B 110.0 . . ? C3 C2 H2B 110.0 . . ? H2A C2 H2B 108.4 . . ? O1 C3 C2 107.2(12) . . ? O1 C3 C4 112.1(13) . . ? C2 C3 C4 109.2(13) . . ? O1 C3 H3 109.5 . . ? C2 C3 H3 109.5 . . ? C4 C3 H3 109.5 . . ? C3 O1 H1 109.5 . . ? N2 C4 C3 109.2(12) . . ? N2 C4 H4A 109.8 . . ? C3 C4 H4A 109.8 . . ? N2 C4 H4B 109.8 . . ? C3 C4 H4B 109.8 . . ? H4A C4 H4B 108.3 . . ? C1 N2 C4 124.6(13) . . ? C1 N2 H2 117.7 . . ? C4 N2 H2 117.7 . . ? C7 C5 C6 119.9(13) . . ? C7 C5 C1 119.4(13) . . ? C6 C5 C1 120.6(13) . . ? C7 C6 C5 120.1(14) 2_656 . ? C7 C6 H6 120.0 2_656 . ? C5 C6 H6 120.0 . . ? C6 C7 C5 120.0(14) 2_656 . ? C6 C7 H7 120.0 2_656 . ? C5 C7 H7 120.0 . . ? N4 Cu1 N3 131.3(7) . . ? N4 Cu1 N5 112.3(7) . . ? N3 Cu1 N5 115.1(6) . . ? N7 Cu2 N6 164.1(7) . . ? N7 Cu2 Cu3 81.4(5) . 2_557 ? N6 Cu2 Cu3 114.5(5) . 2_557 ? N8 N3 Cu1 175.3(15) . . ? C15 N4 Cu1 174.6(15) 1_565 . ? N10 N4 Cu1 174.6(15) 1_565 . ? N6 N5 Cu1 171.4(14) . . ? N5 N6 Cu2 175.8(14) . . ? C14 N7 Cu2 175.6(14) 1_666 . ? N9 N7 Cu2 175.6(14) 1_666 . ? N3 N8 Cu3 171.6(17) . . ? C12 N9 Cu3 167.1(13) 1_444 . ? N7 N9 Cu3 167.1(13) 1_444 . ? C9 N10 Cu3 175.0(14) 1_545 . ? N4 N10 Cu3 175.0(14) 1_545 . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 28.59 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 1.386 _refine_diff_density_min -1.937 _refine_diff_density_rms 0.247 _database_code_depnum_ccdc_archive 'CCDC 924954' ####################################################################### # # 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_e1782b #TrackingRef 'web_deposit_cif_file_3_FERLAY_1361195420.D(1782).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H12 N4, C4 Cu2 N4' _chemical_formula_sum 'C12 H12 Cu2 N8' _chemical_formula_weight 395.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 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' H H 0.0000 0.0000 '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_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.6681(3) _cell_length_b 6.7635(3) _cell_length_c 8.9552(4) _cell_angle_alpha 96.837(2) _cell_angle_beta 108.930(2) _cell_angle_gamma 99.618(2) _cell_volume 370.11(3) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2023 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 27.49 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.774 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 198 _exptl_absorpt_coefficient_mu 2.881 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7616 _exptl_absorpt_correction_T_max 0.8461 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_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 2561 _diffrn_reflns_av_R_equivalents 0.0152 _diffrn_reflns_av_sigmaI/netI 0.0217 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.45 _diffrn_reflns_theta_max 27.19 _reflns_number_total 1573 _reflns_number_gt 1502 _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^)+(0.0327P)^2^+0.2201P] 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 1573 _refine_ls_number_parameters 100 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0219 _refine_ls_R_factor_gt 0.0210 _refine_ls_wR_factor_ref 0.0605 _refine_ls_wR_factor_gt 0.0601 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _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 C1 C 0.4016(3) 0.9254(3) 0.2011(2) 0.0183(3) Uani 1 1 d . . . C2 C 0.1935(3) 0.9645(3) 0.0974(2) 0.0163(3) Uani 1 1 d . . . C3 C 0.0099(3) 0.8069(3) 0.0371(2) 0.0189(3) Uani 1 1 d . . . H3 H 0.0175 0.6756 0.0631 0.023 Uiso 1 1 calc R . . C4 C -0.1851(3) 0.8414(3) -0.0616(2) 0.0193(3) Uani 1 1 d . . . H4 H -0.3112 0.7340 -0.1041 0.023 Uiso 1 1 calc R . . N1 N 0.4609(3) 0.7585(3) 0.15848(19) 0.0246(4) Uani 1 1 d . . . H1A H 0.5835 0.7325 0.2189 0.030 Uiso 1 1 calc R . . H1B H 0.3782 0.6725 0.0695 0.030 Uiso 1 1 calc R . . N2 N 0.5186(3) 1.0582(3) 0.3321(2) 0.0269(4) Uani 1 1 d . . . H2A H 0.6421 1.0371 0.3953 0.032 Uiso 1 1 calc R . . H2B H 0.4739 1.1686 0.3570 0.032 Uiso 1 1 calc R . . Cu1 Cu 0.10427(3) 0.36604(3) 0.46210(3) 0.02004(9) Uani 1 1 d . . . C5 C 0.1251(3) 0.5570(3) 0.7083(2) 0.0191(3) Uani 1 1 d . . . N3 N 0.2506(3) 0.5492(3) 0.82841(19) 0.0247(3) Uani 1 1 d . . . N4 N 0.4099(3) 0.4656(3) 0.4893(2) 0.0208(3) Uani 0.50 1 d P . . C6 C 0.4099(3) 0.4656(3) 0.4893(2) 0.0208(3) Uani 0.50 1 d P . . N5 N 0.0284(3) 0.0835(3) 0.4945(2) 0.0227(3) Uani 0.50 1 d P . . C7 C 0.0284(3) 0.0835(3) 0.4945(2) 0.0227(3) Uani 0.50 1 d P . . 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 C1 0.0146(8) 0.0198(8) 0.0205(8) 0.0047(6) 0.0052(6) 0.0051(7) C2 0.0136(8) 0.0185(8) 0.0164(7) 0.0027(6) 0.0038(6) 0.0056(6) C3 0.0181(8) 0.0143(7) 0.0240(8) 0.0057(6) 0.0055(7) 0.0052(6) C4 0.0134(8) 0.0160(8) 0.0251(9) 0.0023(6) 0.0038(7) 0.0006(6) N1 0.0216(8) 0.0272(8) 0.0217(7) 0.0006(6) 0.0004(6) 0.0141(7) N2 0.0188(8) 0.0275(8) 0.0263(8) -0.0022(7) -0.0025(6) 0.0092(7) Cu1 0.01380(13) 0.01798(13) 0.02578(14) 0.00536(9) 0.00325(9) 0.00317(9) C5 0.0170(8) 0.0168(8) 0.0232(8) 0.0053(6) 0.0069(7) 0.0020(6) N3 0.0241(8) 0.0262(8) 0.0233(8) 0.0045(6) 0.0067(7) 0.0076(7) N4 0.0173(7) 0.0200(8) 0.0234(8) -0.0016(6) 0.0073(6) 0.0034(6) C6 0.0173(7) 0.0200(8) 0.0234(8) -0.0016(6) 0.0073(6) 0.0034(6) N5 0.0144(8) 0.0182(7) 0.0315(9) 0.0052(7) 0.0023(7) 0.0044(6) C7 0.0144(8) 0.0182(7) 0.0315(9) 0.0052(7) 0.0023(7) 0.0044(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N2 1.309(2) . ? C1 N1 1.312(2) . ? C1 C2 1.484(2) . ? C2 C3 1.387(2) . ? C2 C4 1.394(2) 2_575 ? C3 C4 1.390(2) . ? C3 H3 0.9500 . ? C4 C2 1.394(2) 2_575 ? C4 H4 0.9500 . ? N1 H1A 0.8800 . ? N1 H1B 0.8800 . ? N2 H2A 0.8800 . ? N2 H2B 0.8800 . ? Cu1 N4 1.9609(18) . ? Cu1 C5 1.9695(18) 2_566 ? Cu1 N5 1.9737(18) . ? Cu1 C5 2.3688(18) . ? Cu1 Cu1 2.6153(4) 2_566 ? C5 N3 1.142(2) . ? C5 Cu1 1.9694(18) 2_566 ? N4 C6 1.158(3) 2_666 ? N4 N4 1.158(3) 2_666 ? N5 C7 1.156(3) 2_556 ? N5 N5 1.156(3) 2_556 ? 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 C1 N1 122.42(17) . . ? N2 C1 C2 118.77(15) . . ? N1 C1 C2 118.81(15) . . ? C3 C2 C4 120.86(16) . 2_575 ? C3 C2 C1 119.46(16) . . ? C4 C2 C1 119.68(16) 2_575 . ? C2 C3 C4 119.89(16) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C3 C4 C2 119.25(16) . 2_575 ? C3 C4 H4 120.4 . . ? C2 C4 H4 120.4 2_575 . ? C1 N1 H1A 120.0 . . ? C1 N1 H1B 120.0 . . ? H1A N1 H1B 120.0 . . ? C1 N2 H2A 120.0 . . ? C1 N2 H2B 120.0 . . ? H2A N2 H2B 120.0 . . ? N4 Cu1 C5 119.57(8) . 2_566 ? N4 Cu1 N5 115.38(7) . . ? C5 Cu1 N5 113.98(7) 2_566 . ? N4 Cu1 C5 95.54(6) . . ? C5 Cu1 C5 106.50(6) 2_566 . ? N5 Cu1 C5 101.58(7) . . ? N4 Cu1 Cu1 117.33(5) . 2_566 ? C5 Cu1 Cu1 60.28(5) 2_566 2_566 ? N5 Cu1 Cu1 119.20(5) . 2_566 ? C5 Cu1 Cu1 46.22(4) . 2_566 ? N3 C5 Cu1 164.08(16) . 2_566 ? N3 C5 Cu1 122.20(14) . . ? Cu1 C5 Cu1 73.50(6) 2_566 . ? C6 N4 Cu1 176.1(2) 2_666 . ? N4 N4 Cu1 176.1(2) 2_666 . ? C7 N5 Cu1 175.6(2) 2_556 . ? N5 N5 Cu1 175.6(2) 2_556 . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 27.19 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.455 _refine_diff_density_min -0.324 _refine_diff_density_rms 0.063 _database_code_depnum_ccdc_archive 'CCDC 924955' ####################################################################### # # 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_e220 #TrackingRef 'web_deposit_cif_file_4_FERLAY_1361195420.E(220).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C5 H10 N2, C2 Cu N2' _chemical_formula_sum 'C7 H10 Cu N4' _chemical_formula_weight 213.73 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.4930(2) _cell_length_b 8.3120(3) _cell_length_c 11.7280(3) _cell_angle_alpha 90.00 _cell_angle_beta 94.3450(19) _cell_angle_gamma 90.00 _cell_volume 825.54(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2430 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 30.999 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.720 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 436 _exptl_absorpt_coefficient_mu 2.590 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8196 _exptl_absorpt_correction_T_max 0.8814 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_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 4342 _diffrn_reflns_av_R_equivalents 0.0190 _diffrn_reflns_av_sigmaI/netI 0.0390 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.86 _diffrn_reflns_theta_max 31.01 _reflns_number_total 2621 _reflns_number_gt 2096 _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^)+(0.0322P)^2^+0.5105P] 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 2621 _refine_ls_number_parameters 109 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0452 _refine_ls_R_factor_gt 0.0322 _refine_ls_wR_factor_ref 0.0836 _refine_ls_wR_factor_gt 0.0771 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _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 C1 C -0.0012(2) 0.4183(2) 0.46871(15) 0.0194(3) Uani 1 1 d . . . H1A H 0.0013 0.3295 0.5251 0.023 Uiso 1 1 calc R . . H1B H -0.0993 0.4084 0.4180 0.023 Uiso 1 1 calc R . . C2 C 0.13980(19) 0.4073(2) 0.39933(14) 0.0172(3) Uani 1 1 d . . . N1 N 0.27589(17) 0.36035(19) 0.44962(12) 0.0202(3) Uani 1 1 d . . . H1 H 0.2789 0.3277 0.5211 0.024 Uiso 1 1 calc . . . C3 C 0.4234(2) 0.3602(2) 0.39105(15) 0.0218(4) Uani 1 1 d . . . H3A H 0.4403 0.2529 0.3575 0.026 Uiso 1 1 calc R . . H3B H 0.5141 0.3843 0.4465 0.026 Uiso 1 1 calc R . . C4 C 0.4117(2) 0.4858(2) 0.29812(16) 0.0227(4) Uani 1 1 d . . . H4A H 0.5053 0.4796 0.2529 0.027 Uiso 1 1 calc R . . H4B H 0.4085 0.5945 0.3325 0.027 Uiso 1 1 calc R . . C5 C 0.2634(2) 0.4571(3) 0.22143(15) 0.0265(4) Uani 1 1 d . . . H5A H 0.2493 0.5446 0.1643 0.032 Uiso 1 1 calc R . . H5B H 0.2722 0.3541 0.1800 0.032 Uiso 1 1 calc R . . N2 N 0.12700(18) 0.4517(2) 0.29127(13) 0.0237(3) Uani 1 1 d . . . H2 H 0.0335 0.4791 0.2598 0.028 Uiso 1 1 calc . . . Cu1 Cu 0.76386(3) 0.49215(3) 0.122705(18) 0.02089(9) Uani 1 1 d . . . C6 C 0.7329(2) 0.1601(2) 0.26004(13) 0.0172(3) Uani 1 1 d . . . C7 C 0.56105(19) 0.49851(18) 0.02540(14) 0.0167(3) Uani 0.50 1 d P . . N7 N 0.56105(19) 0.49851(18) 0.02540(14) 0.0167(3) Uani 0.50 1 d P . . N3 N 0.75077(18) 0.2683(2) 0.20002(13) 0.0227(3) Uani 1 1 d . . . N4 N 0.9488(2) 0.49269(19) 0.02962(14) 0.0196(3) Uani 0.50 1 d P . . C10 C 0.9488(2) 0.49269(19) 0.02962(14) 0.0196(3) Uani 0.50 1 d P . . 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 C1 0.0158(8) 0.0198(9) 0.0235(8) -0.0013(7) 0.0075(6) -0.0015(6) C2 0.0145(7) 0.0183(8) 0.0192(7) -0.0010(6) 0.0041(6) -0.0008(6) N1 0.0179(7) 0.0262(8) 0.0169(6) 0.0064(6) 0.0046(5) 0.0048(6) C3 0.0149(8) 0.0276(9) 0.0232(8) 0.0045(7) 0.0036(6) 0.0049(7) C4 0.0175(8) 0.0278(10) 0.0232(8) 0.0045(7) 0.0049(7) 0.0014(7) C5 0.0197(9) 0.0446(12) 0.0156(8) 0.0044(8) 0.0047(7) 0.0031(8) N2 0.0133(7) 0.0398(9) 0.0178(7) 0.0026(7) 0.0008(5) 0.0018(7) Cu1 0.01666(13) 0.02600(14) 0.02012(13) -0.00248(9) 0.00209(8) -0.00088(9) C6 0.0182(8) 0.0187(8) 0.0148(7) 0.0008(6) 0.0011(6) 0.0040(6) C7 0.0164(7) 0.0182(7) 0.0157(7) 0.0009(5) 0.0029(5) -0.0009(6) N7 0.0164(7) 0.0182(7) 0.0157(7) 0.0009(5) 0.0029(5) -0.0009(6) N3 0.0228(8) 0.0221(8) 0.0227(7) 0.0002(6) -0.0005(6) 0.0022(6) N4 0.0146(7) 0.0239(8) 0.0203(8) -0.0068(6) 0.0008(6) -0.0019(6) C10 0.0146(7) 0.0239(8) 0.0203(8) -0.0068(6) 0.0008(6) -0.0019(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.501(2) . ? C1 C1 1.543(3) 3_566 ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 N1 1.316(2) . ? C2 N2 1.317(2) . ? N1 C3 1.474(2) . ? N1 H1 0.8800 . ? C3 C4 1.507(2) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.510(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 N2 1.470(2) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? N2 H2 0.8800 . ? Cu1 C6 1.9581(17) 2_655 ? Cu1 N4 1.9798(17) . ? Cu1 C7 1.9936(17) . ? Cu1 N3 2.0764(16) . ? C6 N3 1.159(2) . ? C6 Cu1 1.9581(17) 2_645 ? C7 N7 1.156(3) 3_665 ? C7 C7 1.156(3) 3_665 ? N4 C10 1.160(3) 3_765 ? N4 N4 1.160(3) 3_765 ? 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 C2 C1 C1 109.24(17) . 3_566 ? C2 C1 H1A 109.8 . . ? C1 C1 H1A 109.8 3_566 . ? C2 C1 H1B 109.8 . . ? C1 C1 H1B 109.8 3_566 . ? H1A C1 H1B 108.3 . . ? N1 C2 N2 121.34(15) . . ? N1 C2 C1 118.99(15) . . ? N2 C2 C1 119.59(15) . . ? C2 N1 C3 122.68(14) . . ? C2 N1 H1 118.7 . . ? C3 N1 H1 118.7 . . ? N1 C3 C4 108.95(14) . . ? N1 C3 H3A 109.9 . . ? C4 C3 H3A 109.9 . . ? N1 C3 H3B 109.9 . . ? C4 C3 H3B 109.9 . . ? H3A C3 H3B 108.3 . . ? C3 C4 C5 109.10(16) . . ? C3 C4 H4A 109.9 . . ? C5 C4 H4A 109.9 . . ? C3 C4 H4B 109.9 . . ? C5 C4 H4B 109.9 . . ? H4A C4 H4B 108.3 . . ? N2 C5 C4 109.27(15) . . ? N2 C5 H5A 109.8 . . ? C4 C5 H5A 109.8 . . ? N2 C5 H5B 109.8 . . ? C4 C5 H5B 109.8 . . ? H5A C5 H5B 108.3 . . ? C2 N2 C5 122.27(15) . . ? C2 N2 H2 118.9 . . ? C5 N2 H2 118.9 . . ? C6 Cu1 N4 114.60(7) 2_655 . ? C6 Cu1 C7 110.40(7) 2_655 . ? N4 Cu1 C7 111.81(7) . . ? C6 Cu1 N3 109.29(6) 2_655 . ? N4 Cu1 N3 108.29(6) . . ? C7 Cu1 N3 101.61(6) . . ? N3 C6 Cu1 169.76(16) . 2_645 ? N7 C7 Cu1 176.1(2) 3_665 . ? C7 C7 Cu1 176.1(2) 3_665 . ? C6 N3 Cu1 166.98(14) . . ? C10 N4 Cu1 173.1(2) 3_765 . ? N4 N4 Cu1 173.1(2) 3_765 . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 31.01 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.432 _refine_diff_density_min -0.993 _refine_diff_density_rms 0.085 _database_code_depnum_ccdc_archive 'CCDC 924956' ####################################################################### # # 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_e1613a #TrackingRef 'web_deposit_cif_file_5_FERLAY_1361195420.F(1613).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H20 N4, C6 Cu4 N6, 2(H2 O)' _chemical_formula_sum 'C16 H24 Cu4 N10 O2' _chemical_formula_weight 642.61 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbcn _symmetry_space_group_name_Hall '-P 2n 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 12.1846(4) _cell_length_b 14.9832(4) _cell_length_c 13.1581(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2402.20(13) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7164 _cell_measurement_theta_min 2.72 _cell_measurement_theta_max 27.27 _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.777 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1288 _exptl_absorpt_coefficient_mu 3.527 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6769 _exptl_absorpt_correction_T_max 0.8163 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_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 27778 _diffrn_reflns_av_R_equivalents 0.0418 _diffrn_reflns_av_sigmaI/netI 0.0236 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 27.53 _reflns_number_total 2769 _reflns_number_gt 2364 _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^)+(0.0648P)^2^+8.0945P] 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 2769 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0522 _refine_ls_R_factor_gt 0.0423 _refine_ls_wR_factor_ref 0.1257 _refine_ls_wR_factor_gt 0.1163 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _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 C1 C 0.3431(3) 0.3110(3) 0.7428(3) 0.0268(8) Uani 1 1 d . . . N1 N 0.2782(3) 0.2423(2) 0.7415(2) 0.0285(7) Uani 1 1 d . . . H1 H 0.3017 0.1920 0.7684 0.034 Uiso 1 1 calc R . . C2 C 0.1675(3) 0.2440(3) 0.6974(4) 0.0347(9) Uani 1 1 d . . . H2A H 0.1166 0.2090 0.7403 0.042 Uiso 1 1 calc R . . H2B H 0.1686 0.2171 0.6286 0.042 Uiso 1 1 calc R . . C3 C 0.1297(5) 0.3390(4) 0.6912(6) 0.0678(18) Uani 1 1 d . . . H3A H 0.0630 0.3412 0.6484 0.081 Uiso 1 1 calc R . . H3B H 0.1088 0.3589 0.7603 0.081 Uiso 1 1 calc R . . C4 C 0.2078(4) 0.4006(3) 0.6513(5) 0.0504(13) Uani 1 1 d . . . H4A H 0.1817 0.4625 0.6623 0.061 Uiso 1 1 calc R . . H4B H 0.2161 0.3911 0.5772 0.061 Uiso 1 1 calc R . . N2 N 0.3139(3) 0.3878(2) 0.7020(3) 0.0405(9) Uani 1 1 d . . . H2 H 0.3597 0.4331 0.7053 0.049 Uiso 1 1 calc R . . C5 C 0.4546(3) 0.3038(3) 0.7908(3) 0.0293(8) Uani 1 1 d . . . H5A H 0.4589 0.2480 0.8309 0.035 Uiso 1 1 calc R . . H5B H 0.4660 0.3546 0.8377 0.035 Uiso 1 1 calc R . . Cu1 Cu 0.52933(4) 0.44223(3) 0.06035(4) 0.02766(16) Uani 1 1 d . . . Cu2 Cu 0.63773(4) 0.12447(3) 0.00972(4) 0.02974(16) Uani 1 1 d . . . C6 C 0.5072(3) 0.4579(2) 0.2066(3) 0.0272(7) Uani 0.50 1 d P . . N3 N 0.5072(3) 0.4579(2) 0.2066(3) 0.0272(7) Uani 0.50 1 d P . . C7 C 0.3710(3) 0.4566(3) -0.0068(3) 0.0300(8) Uani 0.50 1 d P . . N4 N 0.3710(3) 0.4566(3) -0.0068(3) 0.0300(8) Uani 0.50 1 d P . . C8 C 0.5822(3) 0.3221(2) 0.0307(3) 0.0244(7) Uani 0.50 1 d P . . N5 N 0.5822(3) 0.3221(2) 0.0307(3) 0.0244(7) Uani 0.50 1 d P . . C9 C 0.6058(3) 0.2481(2) 0.0205(3) 0.0299(8) Uani 0.50 1 d P . . N6 N 0.6058(3) 0.2481(2) 0.0205(3) 0.0299(8) Uani 0.50 1 d P . . C10 C 0.5317(4) 0.0282(3) 0.0030(4) 0.0451(11) Uani 0.50 1 d P . . N7 N 0.5317(4) 0.0282(3) 0.0030(4) 0.0451(11) Uani 0.50 1 d P . . C11 C 0.7858(3) 0.0764(2) 0.0095(3) 0.0262(7) Uani 0.50 1 d P . . N8 N 0.7858(3) 0.0764(2) 0.0095(3) 0.0262(7) Uani 0.50 1 d P . . O1 O 0.3137(5) 0.0765(3) 0.8361(4) 0.0838(15) 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 C1 0.0230(18) 0.0252(18) 0.0322(18) 0.0019(15) -0.0077(15) -0.0009(14) N1 0.0252(17) 0.0230(15) 0.0372(17) 0.0053(13) -0.0062(14) -0.0007(12) C2 0.0234(19) 0.035(2) 0.046(2) 0.0008(18) -0.0065(17) -0.0092(16) C3 0.043(3) 0.064(4) 0.096(5) 0.027(4) -0.026(3) -0.012(3) C4 0.035(3) 0.038(2) 0.079(4) 0.020(2) -0.024(2) -0.001(2) N2 0.0280(19) 0.0249(16) 0.069(3) 0.0105(17) -0.0194(18) -0.0053(14) C5 0.0233(19) 0.0316(19) 0.0329(19) 0.0032(15) -0.0098(15) -0.0004(15) Cu1 0.0256(3) 0.0202(3) 0.0372(3) -0.00299(17) 0.00212(19) -0.00198(17) Cu2 0.0248(3) 0.0217(3) 0.0427(3) 0.00203(19) 0.0065(2) 0.00665(18) C6 0.0251(17) 0.0210(15) 0.0354(16) -0.0034(13) -0.0015(15) 0.0005(14) N3 0.0251(17) 0.0210(15) 0.0354(16) -0.0034(13) -0.0015(15) 0.0005(14) C7 0.030(2) 0.0262(18) 0.0342(18) -0.0021(14) 0.0021(15) -0.0003(15) N4 0.030(2) 0.0262(18) 0.0342(18) -0.0021(14) 0.0021(15) -0.0003(15) C8 0.0223(17) 0.0186(15) 0.0323(16) -0.0003(13) -0.0011(14) 0.0016(13) N5 0.0223(17) 0.0186(15) 0.0323(16) -0.0003(13) -0.0011(14) 0.0016(13) C9 0.0250(19) 0.0284(19) 0.0365(18) 0.0032(15) -0.0003(15) -0.0018(15) N6 0.0250(19) 0.0284(19) 0.0365(18) 0.0032(15) -0.0003(15) -0.0018(15) C10 0.031(2) 0.0242(19) 0.080(3) -0.006(2) 0.019(2) 0.0038(14) N7 0.031(2) 0.0242(19) 0.080(3) -0.006(2) 0.019(2) 0.0038(14) C11 0.0178(17) 0.0165(15) 0.044(2) 0.0000(13) -0.0019(14) 0.0028(13) N8 0.0178(17) 0.0165(15) 0.044(2) 0.0000(13) -0.0019(14) 0.0028(13) O1 0.111(4) 0.052(2) 0.088(3) 0.035(2) -0.010(3) 0.002(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 C1 N1 1.299(5) . ? C1 N2 1.319(5) . ? C1 C5 1.501(5) . ? N1 C2 1.468(5) . ? N1 H1 0.8800 . ? C2 C3 1.498(8) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.426(8) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 N2 1.467(6) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? N2 H2 0.8800 . ? C5 C5 1.542(8) 3_656 ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? Cu1 C8 1.952(3) . ? Cu1 C6 1.958(4) . ? Cu1 N4 2.066(4) 5_665 ? Cu1 C7 2.066(4) 5_665 ? Cu1 C7 2.133(4) . ? Cu1 Cu1 2.4557(10) 5_665 ? Cu2 C9 1.898(4) . ? Cu2 C10 1.939(4) . ? Cu2 C11 1.943(3) . ? C6 N3 1.155(7) 3_655 ? C6 C6 1.155(7) 3_655 ? C7 N8 1.150(5) 4_455 ? C7 C11 1.150(5) 4_455 ? C7 Cu1 2.066(4) 5_665 ? C8 C9 1.153(5) . ? C10 N7 1.146(9) 5_655 ? C10 C10 1.146(9) 5_655 ? C11 N4 1.150(5) 4 ? C11 C7 1.150(5) 4 ? 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 C1 N2 121.4(3) . . ? N1 C1 C5 120.0(3) . . ? N2 C1 C5 118.6(3) . . ? C1 N1 C2 123.4(3) . . ? C1 N1 H1 118.3 . . ? C2 N1 H1 118.3 . . ? N1 C2 C3 108.7(4) . . ? N1 C2 H2A 110.0 . . ? C3 C2 H2A 110.0 . . ? N1 C2 H2B 110.0 . . ? C3 C2 H2B 110.0 . . ? H2A C2 H2B 108.3 . . ? C4 C3 C2 115.5(5) . . ? C4 C3 H3A 108.4 . . ? C2 C3 H3A 108.4 . . ? C4 C3 H3B 108.4 . . ? C2 C3 H3B 108.4 . . ? H3A C3 H3B 107.5 . . ? C3 C4 N2 109.6(4) . . ? C3 C4 H4A 109.8 . . ? N2 C4 H4A 109.8 . . ? C3 C4 H4B 109.8 . . ? N2 C4 H4B 109.8 . . ? H4A C4 H4B 108.2 . . ? C1 N2 C4 122.5(4) . . ? C1 N2 H2 118.7 . . ? C4 N2 H2 118.7 . . ? C1 C5 C5 110.9(4) . 3_656 ? C1 C5 H5A 109.5 . . ? C5 C5 H5A 109.5 3_656 . ? C1 C5 H5B 109.5 . . ? C5 C5 H5B 109.5 3_656 . ? H5A C5 H5B 108.0 . . ? C8 Cu1 C6 110.65(14) . . ? C8 Cu1 N4 114.51(15) . 5_665 ? C6 Cu1 N4 109.14(14) . 5_665 ? C8 Cu1 C7 114.51(15) . 5_665 ? C6 Cu1 C7 109.14(14) . 5_665 ? N4 Cu1 C7 0.0(2) 5_665 5_665 ? C8 Cu1 C7 107.99(14) . . ? C6 Cu1 C7 105.71(15) . . ? N4 Cu1 C7 108.44(13) 5_665 . ? C7 Cu1 C7 108.44(13) 5_665 . ? C8 Cu1 Cu1 128.12(11) . 5_665 ? C6 Cu1 Cu1 120.73(10) . 5_665 ? N4 Cu1 Cu1 55.48(11) 5_665 5_665 ? C7 Cu1 Cu1 55.48(11) 5_665 5_665 ? C7 Cu1 Cu1 52.96(10) . 5_665 ? C9 Cu2 C10 126.37(17) . . ? C9 Cu2 C11 123.51(15) . . ? C10 Cu2 C11 110.08(16) . . ? N3 C6 Cu1 173.04(12) 3_655 . ? C6 C6 Cu1 173.04(12) 3_655 . ? N8 C7 Cu1 146.6(3) 4_455 5_665 ? C11 C7 Cu1 146.6(3) 4_455 5_665 ? N8 C7 Cu1 141.8(3) 4_455 . ? C11 C7 Cu1 141.8(3) 4_455 . ? Cu1 C7 Cu1 71.56(13) 5_665 . ? C9 C8 Cu1 173.0(3) . . ? C8 C9 Cu2 176.4(4) . . ? N7 C10 Cu2 178.6(7) 5_655 . ? C10 C10 Cu2 178.6(7) 5_655 . ? N4 C11 Cu2 175.9(3) 4 . ? C7 C11 Cu2 175.9(3) 4 . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.252 _refine_diff_density_min -0.936 _refine_diff_density_rms 0.136 _database_code_depnum_ccdc_archive 'CCDC 924957' ####################################################################### # # 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_e_a208 #TrackingRef 'web_deposit_cif_file_6_FERLAY_1361195420.G(208).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C5 Cu3 N5, C12 H16 N4' _chemical_formula_sum 'C17 H16 Cu3 N9' _chemical_formula_weight 537.01 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.7515(3) _cell_length_b 12.6791(3) _cell_length_c 13.7566(4) _cell_angle_alpha 90.00 _cell_angle_beta 93.894(2) _cell_angle_gamma 90.00 _cell_volume 1870.96(9) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5467 _cell_measurement_theta_min 2.83 _cell_measurement_theta_max 27.80 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.906 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1072 _exptl_absorpt_coefficient_mu 3.404 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6855 _exptl_absorpt_correction_T_max 0.8218 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_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 19934 _diffrn_reflns_av_R_equivalents 0.0356 _diffrn_reflns_av_sigmaI/netI 0.0329 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 28.03 _reflns_number_total 4513 _reflns_number_gt 3619 _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^)+(0.0379P)^2^+1.0014P] 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 4513 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0430 _refine_ls_R_factor_gt 0.0298 _refine_ls_wR_factor_ref 0.0767 _refine_ls_wR_factor_gt 0.0721 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.002 _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 C1 C 0.3456(2) 0.01190(18) 0.12849(17) 0.0193(5) Uani 1 1 d . . . N22 N 0.3303(2) -0.05984(18) 0.05996(19) 0.0352(6) Uani 1 1 d . . . H1 H 0.2684 -0.0597 0.0147 0.042 Uiso 1 1 calc . . . C2 C 0.4287(3) -0.1403(2) 0.0677(2) 0.0355(7) Uani 1 1 d . . . H2A H 0.4727 -0.1450 0.0070 0.043 Uiso 1 1 calc R . . H2B H 0.3945 -0.2105 0.0828 0.043 Uiso 1 1 calc R . . C3 C 0.5146(2) -0.0985(2) 0.1524(2) 0.0308(6) Uani 1 1 d . . . H3A H 0.5247 -0.1508 0.2058 0.037 Uiso 1 1 calc R . . H3B H 0.5976 -0.0798 0.1307 0.037 Uiso 1 1 calc R . . N2 N 0.4476(2) -0.00496(19) 0.18267(18) 0.0377(6) Uani 1 1 d . . . H2 H 0.4734 0.0354 0.2320 0.045 Uiso 1 1 calc . . . C4 C 0.2597(2) 0.10149(18) 0.13777(17) 0.0196(5) Uani 1 1 d . . . C5 C 0.1342(2) 0.09038(18) 0.10457(18) 0.0218(5) Uani 1 1 d . . . H5 H 0.1031 0.0240 0.0819 0.026 Uiso 1 1 calc R . . C6 C 0.0561(2) 0.17717(18) 0.10512(18) 0.0221(5) Uani 1 1 d . . . H6 H -0.0290 0.1704 0.0826 0.027 Uiso 1 1 calc R . . C7 C 0.1017(2) 0.27473(18) 0.13865(17) 0.0196(5) Uani 1 1 d . . . C8 C 0.2253(2) 0.28409(19) 0.17525(18) 0.0228(5) Uani 1 1 d . . . H8 H 0.2554 0.3497 0.2004 0.027 Uiso 1 1 calc R . . C9 C 0.3042(2) 0.19781(19) 0.17496(18) 0.0229(5) Uani 1 1 d . . . H9 H 0.3884 0.2041 0.2000 0.027 Uiso 1 1 calc R . . C10 C 0.0189(2) 0.36718(19) 0.13286(17) 0.0202(5) Uani 1 1 d . . . N3 N -0.10292(19) 0.36126(17) 0.12529(17) 0.0285(5) Uani 1 1 d . . . H3 H -0.1449 0.3017 0.1220 0.034 Uiso 1 1 calc . . . C11 C -0.1608(3) 0.4658(2) 0.1230(2) 0.0367(7) Uani 1 1 d . . . H11A H -0.2150 0.4750 0.1778 0.044 Uiso 1 1 calc R . . H11B H -0.2106 0.4777 0.0608 0.044 Uiso 1 1 calc R . . C12 C -0.0491(3) 0.5397(2) 0.1329(2) 0.0320(6) Uani 1 1 d . . . H12A H -0.0493 0.5896 0.0775 0.038 Uiso 1 1 calc R . . H12B H -0.0474 0.5800 0.1946 0.038 Uiso 1 1 calc R . . N4 N 0.0569(2) 0.46550(17) 0.13231(18) 0.0320(5) Uani 1 1 d . . . H4 H 0.1355 0.4848 0.1317 0.038 Uiso 1 1 calc . . . Cu1 Cu 0.87644(3) 0.83369(2) 1.10294(2) 0.02541(9) Uani 1 1 d . . . Cu2 Cu 0.53248(3) 0.59112(2) 0.97545(2) 0.02188(9) Uani 1 1 d . . . Cu3 Cu 0.26678(3) 0.83049(3) 0.74760(2) 0.02760(9) Uani 1 1 d . . . C13 C 0.5899(2) 0.46121(19) 0.90711(18) 0.0225(5) Uani 1 1 d . . . N5 N 0.6380(2) 0.41589(16) 0.84758(15) 0.0240(4) Uani 1 1 d . . . C14 C 0.36877(19) 0.73563(17) 0.83345(17) 0.0222(5) Uani 0.50 1 d P . . N6 N 0.36877(19) 0.73563(17) 0.83345(17) 0.0222(5) Uani 0.50 1 d P . . C14A C 0.4245(2) 0.67905(16) 0.88669(17) 0.0213(4) Uani 0.50 1 d P . . N6A N 0.4245(2) 0.67905(16) 0.88669(17) 0.0213(4) Uani 0.50 1 d P . . C15 C 0.1358(2) 0.75230(18) 0.66829(17) 0.0250(5) Uani 0.50 1 d P . . N7 N 0.1358(2) 0.75230(18) 0.66829(17) 0.0250(5) Uani 0.50 1 d P . . C15A C 1.0468(2) 0.78800(19) 1.13336(18) 0.0274(5) Uani 0.50 1 d P . . N7A N 1.0468(2) 0.78800(19) 1.13336(18) 0.0274(5) Uani 0.50 1 d P . . C16 C 0.8343(2) 0.97888(18) 1.13369(18) 0.0254(5) Uani 0.50 1 d P . . N8 N 0.8343(2) 0.97888(18) 1.13369(18) 0.0254(5) Uani 0.50 1 d P . . C16A C 0.1966(2) 0.94414(17) 0.83042(16) 0.0222(5) Uani 0.50 1 d P . . N8A N 0.1966(2) 0.94414(17) 0.83042(16) 0.0222(5) Uani 0.50 1 d P . . C17 C 0.7438(2) 0.73389(17) 1.07062(17) 0.0240(5) Uani 0.50 1 d P . . N9 N 0.7438(2) 0.73389(17) 1.07062(17) 0.0240(5) Uani 0.50 1 d P . . C17A C 0.6643(2) 0.67653(16) 1.04417(16) 0.0215(4) Uani 0.50 1 d P . . N9A N 0.6643(2) 0.67653(16) 1.04417(16) 0.0215(4) Uani 0.50 1 d P . . 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 C1 0.0188(11) 0.0218(11) 0.0171(11) 0.0059(10) 0.0000(9) -0.0049(8) N22 0.0286(12) 0.0317(12) 0.0430(15) -0.0101(11) -0.0147(10) 0.0054(9) C2 0.0300(14) 0.0274(13) 0.0482(19) -0.0044(13) -0.0044(13) 0.0050(11) C3 0.0252(13) 0.0371(14) 0.0297(15) -0.0009(12) -0.0020(11) 0.0085(11) N2 0.0288(12) 0.0442(14) 0.0377(14) -0.0128(12) -0.0146(10) 0.0087(10) C4 0.0196(11) 0.0233(11) 0.0157(11) 0.0035(9) 0.0005(9) -0.0026(9) C5 0.0201(12) 0.0202(11) 0.0248(13) 0.0013(10) -0.0001(9) -0.0056(9) C6 0.0171(11) 0.0257(12) 0.0234(13) 0.0047(10) 0.0004(9) -0.0050(9) C7 0.0201(11) 0.0231(12) 0.0161(11) 0.0016(10) 0.0044(9) -0.0022(9) C8 0.0224(12) 0.0256(12) 0.0203(12) -0.0047(10) 0.0017(9) -0.0055(9) C9 0.0186(11) 0.0296(12) 0.0203(12) -0.0017(11) 0.0002(9) -0.0057(9) C10 0.0232(12) 0.0252(11) 0.0125(11) 0.0011(10) 0.0032(9) -0.0024(9) N3 0.0219(11) 0.0240(10) 0.0398(14) 0.0038(10) 0.0040(9) -0.0008(8) C11 0.0301(15) 0.0277(14) 0.0519(19) -0.0028(13) -0.0013(13) 0.0046(11) C12 0.0365(15) 0.0269(13) 0.0317(15) -0.0020(12) -0.0033(12) 0.0027(11) N4 0.0263(12) 0.0270(11) 0.0414(14) -0.0033(10) -0.0065(10) -0.0025(9) Cu1 0.02338(16) 0.02433(16) 0.02794(18) -0.00138(13) -0.00244(12) 0.00065(11) Cu2 0.02505(16) 0.01785(14) 0.02273(16) -0.00182(12) 0.00141(12) 0.00160(11) Cu3 0.02678(17) 0.02999(17) 0.02620(18) 0.00850(13) 0.00294(13) -0.00329(12) C13 0.0230(12) 0.0227(12) 0.0213(13) -0.0015(10) -0.0025(10) 0.0060(9) N5 0.0307(11) 0.0215(10) 0.0197(11) -0.0001(9) 0.0015(8) 0.0055(8) C14 0.0179(10) 0.0229(10) 0.0257(12) 0.0015(10) 0.0008(9) -0.0031(8) N6 0.0179(10) 0.0229(10) 0.0257(12) 0.0015(10) 0.0008(9) -0.0031(8) C14A 0.0205(11) 0.0204(10) 0.0228(12) 0.0013(9) 0.0005(9) -0.0014(8) N6A 0.0205(11) 0.0204(10) 0.0228(12) 0.0013(9) 0.0005(9) -0.0014(8) C15 0.0221(12) 0.0306(12) 0.0222(12) 0.0031(10) -0.0002(9) 0.0021(9) N7 0.0221(12) 0.0306(12) 0.0222(12) 0.0031(10) -0.0002(9) 0.0021(9) C15A 0.0241(12) 0.0287(12) 0.0291(13) -0.0041(10) -0.0001(10) -0.0016(9) N7A 0.0241(12) 0.0287(12) 0.0291(13) -0.0041(10) -0.0001(10) -0.0016(9) C16 0.0193(11) 0.0250(11) 0.0313(13) 0.0007(10) -0.0024(9) -0.0029(9) N8 0.0193(11) 0.0250(11) 0.0313(13) 0.0007(10) -0.0024(9) -0.0029(9) C16A 0.0197(11) 0.0261(11) 0.0207(12) 0.0010(10) 0.0000(9) -0.0003(8) N8A 0.0197(11) 0.0261(11) 0.0207(12) 0.0010(10) 0.0000(9) -0.0003(8) C17 0.0245(11) 0.0241(11) 0.0231(12) -0.0008(10) 0.0003(9) 0.0032(9) N9 0.0245(11) 0.0241(11) 0.0231(12) -0.0008(10) 0.0003(9) 0.0032(9) C17A 0.0237(11) 0.0203(10) 0.0200(11) 0.0010(9) -0.0016(9) 0.0027(8) N9A 0.0237(11) 0.0203(10) 0.0200(11) 0.0010(9) -0.0016(9) 0.0027(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N2 1.301(3) . ? C1 N22 1.312(3) . ? C1 C4 1.475(3) . ? N22 C2 1.468(3) . ? N22 H1 0.8800 . ? C2 C3 1.531(4) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 N2 1.462(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? N2 H2 0.8800 . ? C4 C9 1.396(3) . ? C4 C5 1.402(3) . ? C5 C6 1.385(3) . ? C5 H5 0.9500 . ? C6 C7 1.398(3) . ? C6 H6 0.9500 . ? C7 C8 1.393(3) . ? C7 C10 1.471(3) . ? C8 C9 1.385(3) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 N3 1.309(3) . ? C10 N4 1.312(3) . ? N3 C11 1.464(3) . ? N3 H3 0.8800 . ? C11 C12 1.522(4) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 N4 1.478(3) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? N4 H4 0.8800 . ? Cu1 C17 1.935(2) . ? Cu1 C15A 1.939(2) . ? Cu1 C16 1.949(2) . ? Cu2 C14A 1.972(2) . ? Cu2 C17A 1.973(2) . ? Cu2 C13 2.014(2) . ? Cu2 C13 2.252(3) 3_667 ? Cu2 Cu2 2.5195(6) 3_667 ? Cu3 C14 1.967(2) . ? Cu3 C15 1.987(2) . ? Cu3 C16A 2.015(2) . ? Cu3 N5 2.029(2) 2_656 ? C13 N5 1.151(3) . ? C13 Cu2 2.252(3) 3_667 ? N5 Cu3 2.029(2) 2_646 ? C14 C14A 1.162(3) . ? C15 N7A 1.160(3) 4_475 ? C15 C15A 1.160(3) 4_475 ? C15A N7 1.160(3) 4_676 ? C15A C15 1.160(3) 4_676 ? C16 N8A 1.153(3) 3_677 ? C16 C16A 1.153(3) 3_677 ? C16A N8 1.153(3) 3_677 ? C16A C16 1.153(3) 3_677 ? C17 C17A 1.162(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 N2 C1 N22 110.9(2) . . ? N2 C1 C4 125.8(2) . . ? N22 C1 C4 123.2(2) . . ? C1 N22 C2 112.0(2) . . ? C1 N22 H1 124.0 . . ? C2 N22 H1 124.0 . . ? N22 C2 C3 102.1(2) . . ? N22 C2 H2A 111.4 . . ? C3 C2 H2A 111.4 . . ? N22 C2 H2B 111.4 . . ? C3 C2 H2B 111.4 . . ? H2A C2 H2B 109.2 . . ? N2 C3 C2 102.4(2) . . ? N2 C3 H3A 111.3 . . ? C2 C3 H3A 111.3 . . ? N2 C3 H3B 111.3 . . ? C2 C3 H3B 111.3 . . ? H3A C3 H3B 109.2 . . ? C1 N2 C3 112.5(2) . . ? C1 N2 H2 123.8 . . ? C3 N2 H2 123.8 . . ? C9 C4 C5 120.4(2) . . ? C9 C4 C1 120.3(2) . . ? C5 C4 C1 119.3(2) . . ? C6 C5 C4 119.3(2) . . ? C6 C5 H5 120.4 . . ? C4 C5 H5 120.4 . . ? C5 C6 C7 120.4(2) . . ? C5 C6 H6 119.8 . . ? C7 C6 H6 119.8 . . ? C8 C7 C6 120.0(2) . . ? C8 C7 C10 120.7(2) . . ? C6 C7 C10 119.3(2) . . ? C9 C8 C7 120.1(2) . . ? C9 C8 H8 120.0 . . ? C7 C8 H8 120.0 . . ? C8 C9 C4 119.8(2) . . ? C8 C9 H9 120.1 . . ? C4 C9 H9 120.1 . . ? N3 C10 N4 111.4(2) . . ? N3 C10 C7 123.9(2) . . ? N4 C10 C7 124.7(2) . . ? C10 N3 C11 111.8(2) . . ? C10 N3 H3 124.1 . . ? C11 N3 H3 124.1 . . ? N3 C11 C12 103.0(2) . . ? N3 C11 H11A 111.2 . . ? C12 C11 H11A 111.2 . . ? N3 C11 H11B 111.2 . . ? C12 C11 H11B 111.2 . . ? H11A C11 H11B 109.1 . . ? N4 C12 C11 102.2(2) . . ? N4 C12 H12A 111.3 . . ? C11 C12 H12A 111.3 . . ? N4 C12 H12B 111.3 . . ? C11 C12 H12B 111.3 . . ? H12A C12 H12B 109.2 . . ? C10 N4 C12 111.3(2) . . ? C10 N4 H4 124.3 . . ? C12 N4 H4 124.3 . . ? C17 Cu1 C15A 121.63(10) . . ? C17 Cu1 C16 119.28(9) . . ? C15A Cu1 C16 117.72(10) . . ? C14A Cu2 C17A 111.09(9) . . ? C14A Cu2 C13 111.07(9) . . ? C17A Cu2 C13 116.07(9) . . ? C14A Cu2 C13 105.23(9) . 3_667 ? C17A Cu2 C13 104.70(9) . 3_667 ? C13 Cu2 C13 107.85(8) . 3_667 ? C14A Cu2 Cu2 121.48(6) . 3_667 ? C17A Cu2 Cu2 125.32(6) . 3_667 ? C14 Cu3 C15 111.72(9) . . ? C14 Cu3 C16A 108.22(9) . . ? C15 Cu3 C16A 112.87(9) . . ? C14 Cu3 N5 115.39(9) . 2_656 ? C15 Cu3 N5 106.37(9) . 2_656 ? C16A Cu3 N5 101.99(9) . 2_656 ? N5 C13 Cu2 155.1(2) . . ? N5 C13 Cu2 132.5(2) . 3_667 ? Cu2 C13 Cu2 72.15(8) . 3_667 ? C13 N5 Cu3 174.8(2) . 2_646 ? C14A C14 Cu3 176.9(2) . . ? C14 C14A Cu2 174.8(2) . . ? N7A C15 Cu3 168.9(2) 4_475 . ? C15A C15 Cu3 168.9(2) 4_475 . ? N7 C15A Cu1 164.0(2) 4_676 . ? C15 C15A Cu1 164.0(2) 4_676 . ? N8A C16 Cu1 166.1(2) 3_677 . ? C16A C16 Cu1 166.1(2) 3_677 . ? N8 C16A Cu3 167.8(2) 3_677 . ? C16 C16A Cu3 167.8(2) 3_677 . ? C17A C17 Cu1 175.0(2) . . ? C17 C17A Cu2 169.4(2) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.03 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.907 _refine_diff_density_min -0.857 _refine_diff_density_rms 0.087 _database_code_depnum_ccdc_archive 'CCDC 924958'