# 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_p21 _audit_creation_date 2013-05-17T15:05:26-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ? _chemical_name_common 'C23 H23 Cl2 Cu N5 O3' _chemical_formula_moiety 'C23 H23 Cl2 Cu N5 O3' _chemical_formula_sum 'C23 H23 Cl2 Cu N5 O3' _chemical_formula_weight 551.9 _chemical_absolute_configuration unk #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.7422(2) _cell_length_b 8.7459(2) _cell_length_c 32.5645(7) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2489.83(10) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 6436 _cell_measurement_theta_min 1.25 _cell_measurement_theta_max 26.47 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.15 _exptl_crystal_density_diffrn 1.472 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1132 _exptl_special_details ? #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 1.126 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7660 _exptl_absorpt_correction_T_max 0.8492 _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BrukerSMART APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_reflns_av_R_equivalents 0.0372 _diffrn_reflns_av_unetI/netI 0.0569 _diffrn_reflns_number 18904 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_theta_min 1.25 _diffrn_reflns_theta_max 26.47 _diffrn_reflns_theta_full 26.47 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _reflns_number_total 4857 _reflns_number_gt 3739 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'SAINT V7.68A (Bruker AXS, 2009)' _computing_cell_refinement 'APEX2 v2011.2-3 (Bruker AXS, 2009)' _computing_data_reduction 'SAINT/SADABS (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'Pov-Ray for windows Vesion 3.6.2., 2009' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0435P)^2^+0.2545P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 4857 _refine_ls_number_parameters 317 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.064 _refine_ls_R_factor_gt 0.0421 _refine_ls_wR_factor_ref 0.0918 _refine_ls_wR_factor_gt 0.0859 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.016(15) _refine_diff_density_max 0.397 _refine_diff_density_min -0.332 _refine_diff_density_rms 0.059 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 1.05979(5) 0.73361(5) 0.104864(13) 0.03657(13) Uani 1 1 d . . . Cl2 Cl 0.94551(13) 0.53260(11) 0.07662(3) 0.0546(3) Uani 1 1 d . . . Cl1 Cl 1.27813(12) 0.63102(13) 0.14188(3) 0.0557(3) Uani 1 1 d . . . N2 N 0.9169(3) 0.7485(4) 0.15465(9) 0.0384(7) Uani 1 1 d . . . N1 N 1.0759(3) 0.9476(3) 0.11978(9) 0.0353(7) Uani 1 1 d . . . N5 N 1.2222(4) 0.7338(4) 0.02238(9) 0.0445(8) Uani 1 1 d . . . N4 N 1.1799(3) 0.8222(4) 0.05604(9) 0.0391(8) Uani 1 1 d . . . N3 N 0.8243(4) 0.6291(4) 0.16689(11) 0.0426(9) Uani 1 1 d . . . C17 C 1.1561(4) 0.7601(6) -0.01449(12) 0.0439(10) Uani 1 1 d . . . C13 C 0.4907(5) 0.3047(6) 0.19396(16) 0.0672(15) Uani 1 1 d . . . H13 H 0.4071 0.291 0.1767 0.081 Uiso 1 1 calc R . . C6 C 0.9143(4) 0.8772(4) 0.17404(11) 0.0389(9) Uani 1 1 d . . . C2 C 1.1721(4) 1.1931(4) 0.10591(14) 0.0448(10) Uani 1 1 d . . . H2 H 1.2257 1.2597 0.0889 0.054 Uiso 1 1 calc R . . C8 C 1.2129(4) 0.9658(4) 0.05752(12) 0.0369(9) Uani 1 1 d . . . C11 C 0.7188(4) 0.4369(4) 0.21104(12) 0.0355(9) Uani 1 1 d . . . C18 C 1.1734(4) 0.6354(5) -0.04585(12) 0.0464(10) Uani 1 1 d . . . C15 C 0.6285(6) 0.2304(6) 0.25312(14) 0.0613(12) Uani 1 1 d . . . H15 H 0.6389 0.1673 0.2759 0.074 Uiso 1 1 calc R . . C5 C 1.0101(4) 0.9955(4) 0.15454(11) 0.0352(9) Uani 1 1 d . . . C4 C 1.0278(4) 1.1474(4) 0.16669(12) 0.0453(10) Uani 1 1 d . . . H4 H 0.9848 1.1816 0.1912 0.054 Uiso 1 1 calc R . . C7 C 0.8139(5) 0.9167(5) 0.20952(14) 0.0564(12) Uani 1 1 d . . . H7A H 0.7267 0.85 0.2098 0.085 Uiso 1 1 calc R . . H7B H 0.7803 1.0208 0.207 0.085 Uiso 1 1 calc R . . H7C H 0.8702 0.9048 0.2346 0.085 Uiso 1 1 calc R . . C3 C 1.1081(4) 1.2449(5) 0.14253(13) 0.0502(10) Uani 1 1 d . . . H3 H 1.1205 1.3463 0.1504 0.06 Uiso 1 1 calc R . . C10 C 0.8304(5) 0.5640(5) 0.20512(13) 0.0386(9) Uani 1 1 d . . . C12 C 0.5952(4) 0.4173(5) 0.18588(13) 0.0486(11) Uani 1 1 d . . . H12 H 0.582 0.4807 0.1632 0.058 Uiso 1 1 calc R . . C1 C 1.1546(4) 1.0409(4) 0.09528(12) 0.0373(9) Uani 1 1 d . . . C9 C 1.3053(5) 1.0533(5) 0.02740(13) 0.0525(11) Uani 1 1 d . . . H9A H 1.3504 0.984 0.008 0.079 Uiso 1 1 calc R . . H9B H 1.3846 1.1079 0.0415 0.079 Uiso 1 1 calc R . . H9C H 1.2407 1.1245 0.0132 0.079 Uiso 1 1 calc R . . C16 C 0.7355(5) 0.3438(5) 0.24529(13) 0.0513(11) Uani 1 1 d . . . H16 H 0.8181 0.3574 0.2629 0.062 Uiso 1 1 calc R . . C21 C 1.1729(6) 0.4074(7) -0.10442(19) 0.0790(16) Uani 1 1 d . . . H21 H 1.1701 0.3299 -0.124 0.095 Uiso 1 1 calc R . . C23 C 1.2567(5) 0.5056(6) -0.03923(16) 0.0657(14) Uani 1 1 d . . . H23 H 1.3122 0.4949 -0.015 0.079 Uiso 1 1 calc R . . C14 C 0.5097(6) 0.2126(6) 0.22744(16) 0.0679(15) Uani 1 1 d . . . H14 H 0.4388 0.1357 0.2326 0.081 Uiso 1 1 calc R . . C19 C 1.0920(5) 0.6522(6) -0.08217(13) 0.0596(12) Uani 1 1 d . . . H19 H 1.0367 0.7412 -0.087 0.071 Uiso 1 1 calc R . . C20 C 1.0933(6) 0.5372(7) -0.11104(16) 0.0767(15) Uani 1 1 d . . . H20 H 1.0387 0.5491 -0.1353 0.092 Uiso 1 1 calc R . . C22 C 1.2595(6) 0.3870(6) -0.06888(19) 0.0801(16) Uani 1 1 d . . . H22 H 1.3169 0.2989 -0.0648 0.096 Uiso 1 1 calc R . . O1 O 0.9146(3) 0.6113(3) 0.23190(9) 0.0597(8) Uani 1 1 d . . . O2 O 1.0875(3) 0.8785(4) -0.02152(9) 0.0553(8) Uani 1 1 d . . . O3 O 0.8678(4) 0.0394(4) 0.93741(12) 0.0909(12) Uani 1 1 d . . . H3A H 0.810(5) 0.574(5) 0.1468(13) 0.052(14) Uiso 1 1 d . . . H5A H 1.247(5) 0.629(6) 0.0316(15) 0.086(17) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0484(2) 0.0285(2) 0.0329(2) 0.0013(2) 0.0023(2) -0.0017(2) Cl2 0.0734(7) 0.0427(6) 0.0476(6) -0.0053(5) -0.0126(6) -0.0094(6) Cl1 0.0562(6) 0.0549(7) 0.0559(7) 0.0074(6) -0.0129(5) 0.0061(5) N2 0.0421(17) 0.0338(17) 0.0392(17) 0.0039(16) 0.0047(13) -0.0075(17) N1 0.0451(18) 0.0278(15) 0.0329(17) 0.0051(13) 0.0007(15) -0.0001(15) N5 0.061(2) 0.041(2) 0.0314(19) 0.0021(18) 0.0094(15) 0.0107(19) N4 0.0484(19) 0.039(2) 0.0302(19) 0.0029(15) 0.0029(15) 0.0051(15) N3 0.055(2) 0.040(2) 0.032(2) 0.0002(18) 0.0023(17) -0.0156(17) C17 0.039(2) 0.049(3) 0.044(2) 0.002(2) 0.0024(18) -0.003(2) C13 0.053(3) 0.070(4) 0.078(4) 0.009(3) -0.003(2) -0.024(2) C6 0.042(2) 0.041(2) 0.034(2) 0.0009(19) 0.0000(18) 0.0030(19) C2 0.055(2) 0.034(2) 0.046(2) 0.006(2) -0.001(2) -0.0070(17) C8 0.036(2) 0.037(2) 0.038(2) 0.0098(19) 0.0003(17) 0.0002(17) C11 0.041(2) 0.029(2) 0.037(2) 0.0008(18) 0.0091(19) 0.0060(17) C18 0.044(2) 0.058(3) 0.038(3) -0.005(2) 0.0065(19) -0.008(2) C15 0.087(3) 0.048(3) 0.049(3) 0.019(3) 0.020(3) -0.007(3) C5 0.037(2) 0.032(2) 0.036(2) -0.0016(18) -0.0015(16) 0.0023(16) C4 0.055(2) 0.035(2) 0.046(3) -0.008(2) 0.001(2) 0.0035(19) C7 0.066(3) 0.050(3) 0.053(3) -0.005(2) 0.018(2) -0.003(2) C3 0.063(2) 0.030(2) 0.058(3) -0.001(2) -0.006(2) -0.004(2) C10 0.041(2) 0.042(2) 0.032(2) 0.000(2) 0.0016(19) 0.0023(19) C12 0.046(3) 0.051(3) 0.049(3) 0.009(2) 0.000(2) -0.004(2) C1 0.041(2) 0.032(2) 0.039(2) 0.0084(19) -0.0031(18) 0.0024(17) C9 0.062(3) 0.050(3) 0.046(3) 0.009(2) 0.012(2) -0.005(2) C16 0.063(3) 0.056(3) 0.034(2) 0.001(2) 0.002(2) 0.007(2) C21 0.082(4) 0.089(4) 0.066(4) -0.037(4) 0.022(3) -0.017(3) C23 0.065(3) 0.066(3) 0.065(3) -0.017(3) -0.004(2) 0.002(3) C14 0.067(3) 0.056(3) 0.081(4) 0.008(3) 0.028(3) -0.017(2) C19 0.060(3) 0.077(3) 0.042(3) -0.005(3) 0.004(2) -0.011(3) C20 0.072(3) 0.100(4) 0.058(4) -0.016(3) 0.005(3) -0.019(3) C22 0.085(4) 0.064(4) 0.091(4) -0.021(3) 0.022(3) 0.003(3) O1 0.0640(19) 0.064(2) 0.0507(19) 0.0092(16) -0.0137(16) -0.0109(17) O2 0.0601(19) 0.0592(19) 0.0465(18) -0.0017(15) -0.0076(14) 0.0130(17) O3 0.112(3) 0.062(2) 0.099(3) 0.000(2) -0.032(2) 0.029(2) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N1 1.938(3) . ? Cu1 N2 2.051(3) . ? Cu1 N4 2.057(3) . ? Cu1 Cl2 2.2214(10) . ? Cu1 Cl1 2.4293(11) . ? N2 C6 1.291(5) . ? N2 N3 1.381(4) . ? N1 C1 1.333(4) . ? N1 C5 1.337(4) . ? N5 C17 1.353(5) . ? N5 N4 1.391(4) . ? N5 H5A 0.99(5) . ? N4 C8 1.289(5) . ? N3 C10 1.370(5) . ? N3 H3A 0.82(4) . ? C17 O2 1.218(5) . ? C17 C18 1.502(6) . ? C13 C14 1.366(7) . ? C13 C12 1.368(6) . ? C13 H13 0.93 . ? C6 C5 1.475(5) . ? C6 C7 1.492(6) . ? C2 C1 1.384(5) . ? C2 C3 1.393(6) . ? C2 H2 0.93 . ? C8 C9 1.483(5) . ? C8 C1 1.485(5) . ? C11 C12 1.367(5) . ? C11 C16 1.389(5) . ? C11 C10 1.491(5) . ? C18 C23 1.366(6) . ? C18 C19 1.388(6) . ? C15 C14 1.342(7) . ? C15 C16 1.387(6) . ? C15 H15 0.93 . ? C5 C4 1.395(5) . ? C4 C3 1.356(6) . ? C4 H4 0.93 . ? C7 H7A 0.96 . ? C7 H7B 0.96 . ? C7 H7C 0.96 . ? C3 H3 0.93 . ? C10 O1 1.214(5) . ? C12 H12 0.93 . ? C9 H9A 0.96 . ? C9 H9B 0.96 . ? C9 H9C 0.96 . ? C16 H16 0.93 . ? C21 C20 1.349(7) . ? C21 C22 1.394(8) . ? C21 H21 0.93 . ? C23 C22 1.417(7) . ? C23 H23 0.93 . ? C14 H14 0.93 . ? C19 C20 1.377(7) . ? C19 H19 0.93 . ? C20 H20 0.93 . ? C22 H22 0.93 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 N2 77.59(12) . . ? N1 Cu1 N4 78.05(13) . . ? N2 Cu1 N4 153.92(12) . . ? N1 Cu1 Cl2 154.22(10) . . ? N2 Cu1 Cl2 95.95(9) . . ? N4 Cu1 Cl2 101.99(10) . . ? N1 Cu1 Cl1 100.08(10) . . ? N2 Cu1 Cl1 96.29(9) . . ? N4 Cu1 Cl1 96.97(9) . . ? Cl2 Cu1 Cl1 105.46(4) . . ? C6 N2 N3 120.5(3) . . ? C6 N2 Cu1 116.9(2) . . ? N3 N2 Cu1 122.5(2) . . ? C1 N1 C5 122.5(3) . . ? C1 N1 Cu1 118.6(2) . . ? C5 N1 Cu1 118.9(2) . . ? C17 N5 N4 119.4(3) . . ? C17 N5 H5A 121(3) . . ? N4 N5 H5A 109(3) . . ? C8 N4 N5 120.7(3) . . ? C8 N4 Cu1 116.9(3) . . ? N5 N4 Cu1 122.4(2) . . ? C10 N3 N2 123.6(3) . . ? C10 N3 H3A 119(3) . . ? N2 N3 H3A 108(3) . . ? O2 C17 N5 121.5(4) . . ? O2 C17 C18 122.6(4) . . ? N5 C17 C18 115.9(4) . . ? C14 C13 C12 119.8(5) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? N2 C6 C5 113.0(3) . . ? N2 C6 C7 126.3(4) . . ? C5 C6 C7 120.3(4) . . ? C1 C2 C3 118.8(4) . . ? C1 C2 H2 120.6 . . ? C3 C2 H2 120.6 . . ? N4 C8 C9 126.8(4) . . ? N4 C8 C1 112.7(3) . . ? C9 C8 C1 120.4(3) . . ? C12 C11 C16 119.4(4) . . ? C12 C11 C10 122.2(4) . . ? C16 C11 C10 118.2(4) . . ? C23 C18 C19 119.7(4) . . ? C23 C18 C17 123.4(4) . . ? C19 C18 C17 116.8(4) . . ? C14 C15 C16 119.4(4) . . ? C14 C15 H15 120.3 . . ? C16 C15 H15 120.3 . . ? N1 C5 C4 119.4(3) . . ? N1 C5 C6 112.9(3) . . ? C4 C5 C6 127.5(4) . . ? C3 C4 C5 119.4(4) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? 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 . . ? C4 C3 C2 120.0(4) . . ? C4 C3 H3 120 . . ? C2 C3 H3 120 . . ? O1 C10 N3 122.3(4) . . ? O1 C10 C11 123.9(4) . . ? N3 C10 C11 113.7(3) . . ? C11 C12 C13 120.2(4) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? N1 C1 C2 119.8(4) . . ? N1 C1 C8 113.7(3) . . ? C2 C1 C8 126.5(4) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C15 C16 C11 119.8(4) . . ? C15 C16 H16 120.1 . . ? C11 C16 H16 120.1 . . ? C20 C21 C22 121.3(5) . . ? C20 C21 H21 119.3 . . ? C22 C21 H21 119.3 . . ? C18 C23 C22 120.6(5) . . ? C18 C23 H23 119.7 . . ? C22 C23 H23 119.7 . . ? C15 C14 C13 121.5(4) . . ? C15 C14 H14 119.2 . . ? C13 C14 H14 119.2 . . ? C20 C19 C18 120.0(5) . . ? C20 C19 H19 120 . . ? C18 C19 H19 120 . . ? C21 C20 C19 120.7(5) . . ? C21 C20 H20 119.7 . . ? C19 C20 H20 119.7 . . ? C21 C22 C23 117.6(5) . . ? C21 C22 H22 121.2 . . ? C23 C22 H22 121.2 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 Cu1 N2 C6 -6.1(3) . . . . ? N4 Cu1 N2 C6 -27.4(4) . . . . ? Cl2 Cu1 N2 C6 -160.8(3) . . . . ? Cl1 Cu1 N2 C6 92.8(3) . . . . ? N1 Cu1 N2 N3 172.4(3) . . . . ? N4 Cu1 N2 N3 151.2(3) . . . . ? Cl2 Cu1 N2 N3 17.7(3) . . . . ? Cl1 Cu1 N2 N3 -88.6(3) . . . . ? N2 Cu1 N1 C1 -173.4(3) . . . . ? N4 Cu1 N1 C1 -2.8(3) . . . . ? Cl2 Cu1 N1 C1 -95.7(3) . . . . ? Cl1 Cu1 N1 C1 92.3(3) . . . . ? N2 Cu1 N1 C5 7.7(3) . . . . ? N4 Cu1 N1 C5 178.3(3) . . . . ? Cl2 Cu1 N1 C5 85.4(3) . . . . ? Cl1 Cu1 N1 C5 -86.6(3) . . . . ? C17 N5 N4 C8 -67.4(5) . . . . ? C17 N5 N4 Cu1 111.4(3) . . . . ? N1 Cu1 N4 C8 1.7(3) . . . . ? N2 Cu1 N4 C8 22.9(5) . . . . ? Cl2 Cu1 N4 C8 155.3(3) . . . . ? Cl1 Cu1 N4 C8 -97.2(3) . . . . ? N1 Cu1 N4 N5 -177.2(3) . . . . ? N2 Cu1 N4 N5 -156.0(3) . . . . ? Cl2 Cu1 N4 N5 -23.5(3) . . . . ? Cl1 Cu1 N4 N5 84.0(3) . . . . ? C6 N2 N3 C10 -59.6(5) . . . . ? Cu1 N2 N3 C10 121.9(4) . . . . ? N4 N5 C17 O2 16.8(5) . . . . ? N4 N5 C17 C18 -163.5(3) . . . . ? N3 N2 C6 C5 -174.9(3) . . . . ? Cu1 N2 C6 C5 3.7(4) . . . . ? N3 N2 C6 C7 -2.0(6) . . . . ? Cu1 N2 C6 C7 176.6(3) . . . . ? N5 N4 C8 C9 -4.8(6) . . . . ? Cu1 N4 C8 C9 176.3(3) . . . . ? N5 N4 C8 C1 178.5(3) . . . . ? Cu1 N4 C8 C1 -0.4(4) . . . . ? O2 C17 C18 C23 176.4(4) . . . . ? N5 C17 C18 C23 -3.3(6) . . . . ? O2 C17 C18 C19 -7.4(6) . . . . ? N5 C17 C18 C19 172.9(3) . . . . ? C1 N1 C5 C4 -2.2(5) . . . . ? Cu1 N1 C5 C4 176.6(3) . . . . ? C1 N1 C5 C6 173.2(3) . . . . ? Cu1 N1 C5 C6 -8.0(4) . . . . ? N2 C6 C5 N1 2.4(5) . . . . ? C7 C6 C5 N1 -170.9(3) . . . . ? N2 C6 C5 C4 177.4(4) . . . . ? C7 C6 C5 C4 4.0(6) . . . . ? N1 C5 C4 C3 1.7(6) . . . . ? C6 C5 C4 C3 -173.0(4) . . . . ? C5 C4 C3 C2 0.0(6) . . . . ? C1 C2 C3 C4 -1.3(6) . . . . ? N2 N3 C10 O1 3.0(6) . . . . ? N2 N3 C10 C11 179.9(3) . . . . ? C12 C11 C10 O1 159.0(4) . . . . ? C16 C11 C10 O1 -15.7(6) . . . . ? C12 C11 C10 N3 -17.9(5) . . . . ? C16 C11 C10 N3 167.4(3) . . . . ? C16 C11 C12 C13 -1.4(6) . . . . ? C10 C11 C12 C13 -176.0(4) . . . . ? C14 C13 C12 C11 0.5(7) . . . . ? C5 N1 C1 C2 1.0(5) . . . . ? Cu1 N1 C1 C2 -177.9(3) . . . . ? C5 N1 C1 C8 -177.7(3) . . . . ? Cu1 N1 C1 C8 3.4(4) . . . . ? C3 C2 C1 N1 0.8(6) . . . . ? C3 C2 C1 C8 179.3(3) . . . . ? N4 C8 C1 N1 -1.8(5) . . . . ? C9 C8 C1 N1 -178.8(3) . . . . ? N4 C8 C1 C2 179.6(4) . . . . ? C9 C8 C1 C2 2.6(6) . . . . ? C14 C15 C16 C11 -0.2(7) . . . . ? C12 C11 C16 C15 1.2(6) . . . . ? C10 C11 C16 C15 176.1(4) . . . . ? C19 C18 C23 C22 -0.8(7) . . . . ? C17 C18 C23 C22 175.3(4) . . . . ? C16 C15 C14 C13 -0.8(7) . . . . ? C12 C13 C14 C15 0.6(8) . . . . ? C23 C18 C19 C20 1.2(6) . . . . ? C17 C18 C19 C20 -175.2(4) . . . . ? C22 C21 C20 C19 -1.8(8) . . . . ? C18 C19 C20 C21 0.1(7) . . . . ? C20 C21 C22 C23 2.1(8) . . . . ? C18 C23 C22 C21 -0.8(7) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3 H3A Cl2 0.82(4) 2.60(4) 3.237(4) 135(4) . N5 H5A O3 0.99(5) 2.08(5) 3.007(5) 156(4) 4_556 # END of CIF _database_code_depnum_ccdc_archive 'CCDC 907860' ####################################################################### # # 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_ccg_bf17_0m _audit_creation_date 2013-05-17T15:09:39-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ? _chemical_name_common 'C23 H23 Br2 Cu N5 O3' _chemical_formula_moiety 'C23 H23 Br2 Cu N5 O3' _chemical_formula_sum 'C23 H23 Br2 Cu N5 O3' _chemical_formula_weight 640.82 _chemical_absolute_configuration unk #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.6632(2) _cell_length_b 8.8145(2) _cell_length_c 33.2879(6) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2541.92(9) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 7237 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 29.17 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.32 _exptl_crystal_density_diffrn 1.675 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1276 _exptl_special_details ? #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 4.037 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2399 _exptl_absorpt_correction_T_max 0.3582 _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_reflns_av_R_equivalents 0.0327 _diffrn_reflns_av_unetI/netI 0.0463 _diffrn_reflns_number 26959 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -44 _diffrn_reflns_limit_l_max 45 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 29.17 _diffrn_reflns_theta_full 29.17 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 6833 _reflns_number_gt 5458 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'SAINT V7.68A (Bruker AXS, 2009)' _computing_cell_refinement 'APEX2 v2011.2-3 (Bruker AXS, 2009)' _computing_data_reduction 'SAINT/SADABS (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'Pov-Ray for windows Vesion 3.6.2., 2009' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0253P)^2^+0.2729P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 6833 _refine_ls_number_parameters 317 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0487 _refine_ls_R_factor_gt 0.0324 _refine_ls_wR_factor_ref 0.0704 _refine_ls_wR_factor_gt 0.0659 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.013(7) _refine_diff_density_max 0.471 _refine_diff_density_min -0.316 _refine_diff_density_rms 0.06 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Br2 Br 0.57699(4) 0.47889(4) 0.075742(10) 0.05394(10) Uani 1 1 d . . . Cu1 Cu 0.45369(4) 0.26954(4) 0.106264(9) 0.03801(9) Uani 1 1 d . . . Br1 Br 0.21878(4) 0.37356(4) 0.143722(11) 0.05973(10) Uani 1 1 d . . . N1 N 0.4385(3) 0.0578(2) 0.12191(6) 0.0366(5) Uani 1 1 d . . . C3 C 0.4035(4) -0.2325(3) 0.14560(10) 0.0522(8) Uani 1 1 d . . . H3 H 0.3894 -0.3324 0.1539 0.063 Uiso 1 1 calc R . . C2 C 0.3427(4) -0.1860(3) 0.10921(10) 0.0493(8) Uani 1 1 d . . . H2 H 0.2908 -0.2539 0.0927 0.059 Uiso 1 1 calc R . . C5 C 0.5015(3) 0.0144(3) 0.15635(8) 0.0390(6) Uani 1 1 d . . . C8 C 0.3037(3) 0.0365(3) 0.06045(8) 0.0389(6) Uani 1 1 d . . . C1 C 0.3610(3) -0.0365(3) 0.09809(8) 0.0372(6) Uani 1 1 d . . . C9 C 0.2140(4) -0.0545(4) 0.03088(9) 0.0530(8) Uani 1 1 d . . . H9A H 0.1699 0.0119 0.0111 0.079 Uiso 1 1 calc R . . H9B H 0.133 -0.108 0.0445 0.079 Uiso 1 1 calc R . . H9C H 0.2812 -0.1259 0.0179 0.079 Uiso 1 1 calc R . . C7 C 0.6916(4) 0.0983(4) 0.21123(11) 0.0626(10) Uani 1 1 d . . . H7A H 0.7719 0.1727 0.2138 0.094 Uiso 1 1 calc R . . H7B H 0.7368 -0.0004 0.208 0.094 Uiso 1 1 calc R . . H7C H 0.6282 0.0994 0.2349 0.094 Uiso 1 1 calc R . . C4 C 0.4840(4) -0.1345(4) 0.16973(9) 0.0480(7) Uani 1 1 d . . . H4 H 0.5255 -0.166 0.1941 0.058 Uiso 1 1 calc R . . C6 C 0.5955(3) 0.1341(4) 0.17557(9) 0.0429(6) Uani 1 1 d . . . N4 N 0.3361(3) 0.1786(3) 0.05853(7) 0.0393(6) Uani 1 1 d . . . N2 N 0.5925(3) 0.2592(3) 0.15604(7) 0.0412(5) Uani 1 1 d . . . N5 N 0.2925(3) 0.2619(3) 0.02511(7) 0.0456(6) Uani 1 1 d . . . N3 N 0.6829(3) 0.3797(3) 0.16806(8) 0.0475(7) Uani 1 1 d . . . C17 C 0.3610(3) 0.2382(4) -0.01080(9) 0.0405(6) Uani 1 1 d . . . C10 C 0.6749(4) 0.4481(4) 0.20539(9) 0.0429(7) Uani 1 1 d . . . O2 O 0.4359(2) 0.1234(3) -0.01690(6) 0.0540(5) Uani 1 1 d . . . O1 O 0.5904(3) 0.4024(3) 0.23153(6) 0.0640(7) Uani 1 1 d . . . C18 C 0.3417(3) 0.3595(4) -0.04166(9) 0.0458(7) Uani 1 1 d . . . C11 C 0.7843(4) 0.5756(3) 0.21010(8) 0.0404(6) Uani 1 1 d . . . C19 C 0.4120(4) 0.3378(4) -0.07818(10) 0.0601(9) Uani 1 1 d . . . H19 H 0.4641 0.2475 -0.0833 0.072 Uiso 1 1 calc R . . C12 C 0.9035(4) 0.6044(4) 0.18388(10) 0.0553(9) Uani 1 1 d . . . H12 H 0.9145 0.544 0.1611 0.066 Uiso 1 1 calc R . . C16 C 0.7728(5) 0.6672(4) 0.24437(9) 0.0567(9) Uani 1 1 d . . . H16 H 0.6928 0.6516 0.2625 0.068 Uiso 1 1 calc R . . C23 C 0.2631(5) 0.4941(5) -0.03447(12) 0.0699(11) Uani 1 1 d . . . H23 H 0.2158 0.5098 -0.0097 0.084 Uiso 1 1 calc R . . C20 C 0.4060(5) 0.4493(5) -0.10752(12) 0.0768(12) Uani 1 1 d . . . H20 H 0.4548 0.4343 -0.1321 0.092 Uiso 1 1 calc R . . C15 C 0.8791(5) 0.7800(4) 0.25131(11) 0.0690(11) Uani 1 1 d . . . H15 H 0.8725 0.838 0.2746 0.083 Uiso 1 1 calc R . . C21 C 0.3284(5) 0.5811(6) -0.10025(14) 0.0807(13) Uani 1 1 d . . . H21 H 0.325 0.6556 -0.12 0.097 Uiso 1 1 calc R . . C13 C 1.0065(4) 0.7200(5) 0.19046(13) 0.0759(12) Uani 1 1 d . . . H13 H 1.0846 0.7391 0.172 0.091 Uiso 1 1 calc R . . C22 C 0.2545(5) 0.6059(5) -0.06391(15) 0.0832(14) Uani 1 1 d . . . H22 H 0.2004 0.6953 -0.0593 0.1 Uiso 1 1 calc R . . C14 C 0.9938(5) 0.8074(5) 0.22443(13) 0.0732(12) Uani 1 1 d . . . H14 H 1.0638 0.8855 0.2291 0.088 Uiso 1 1 calc R . . O3 O 0.6300(5) 0.9460(4) 0.93835(10) 0.1120(13) Uani 1 1 d . . . H5A H 0.267(4) 0.344(4) 0.0296(9) 0.043(9) Uiso 1 1 d . . . H3A H 0.698(4) 0.419(4) 0.1514(10) 0.045(11) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br2 0.0745(2) 0.04102(18) 0.04635(17) 0.00560(13) 0.01154(16) -0.00884(15) Cu1 0.0525(2) 0.02832(17) 0.03325(16) -0.00132(13) -0.00127(16) -0.00113(15) Br1 0.0634(2) 0.0577(2) 0.0581(2) -0.00868(17) 0.01473(17) 0.00779(17) N1 0.0445(13) 0.0275(12) 0.0377(11) -0.0014(9) -0.0020(10) -0.0001(10) C3 0.073(2) 0.0279(15) 0.0556(18) 0.0070(14) 0.0070(17) -0.0009(15) C2 0.0602(19) 0.0326(17) 0.0551(18) -0.0070(14) 0.0015(16) -0.0059(13) C5 0.0447(15) 0.0335(15) 0.0388(14) 0.0005(12) 0.0013(12) 0.0026(12) C8 0.0401(15) 0.0379(17) 0.0387(14) -0.0040(12) 0.0026(12) 0.0000(13) C1 0.0427(14) 0.0313(15) 0.0375(15) -0.0049(11) 0.0038(11) 0.0021(12) C9 0.064(2) 0.050(2) 0.0450(17) -0.0053(14) -0.0073(16) -0.0128(17) C7 0.070(2) 0.056(2) 0.061(2) 0.0111(17) -0.0220(19) -0.0004(18) C4 0.0607(19) 0.0381(17) 0.0451(16) 0.0057(14) 0.0000(14) 0.0049(15) C6 0.0430(16) 0.0423(17) 0.0435(15) -0.0002(13) -0.0051(13) 0.0006(13) N4 0.0505(14) 0.0351(14) 0.0323(11) -0.0034(9) -0.0034(10) 0.0043(10) N2 0.0458(13) 0.0384(14) 0.0394(12) -0.0039(10) -0.0023(10) -0.0057(11) N5 0.0612(16) 0.0378(16) 0.0378(13) -0.0018(11) -0.0052(12) 0.0155(13) N3 0.0616(18) 0.0464(16) 0.0344(14) -0.0028(13) -0.0005(12) -0.0166(14) C17 0.0342(14) 0.0422(18) 0.0453(16) 0.0003(13) -0.0053(12) -0.0015(13) C10 0.0514(18) 0.0426(18) 0.0348(15) -0.0003(12) -0.0051(13) 0.0067(14) O2 0.0565(13) 0.0578(15) 0.0477(11) 0.0046(10) 0.0084(10) 0.0171(12) O1 0.0751(16) 0.0697(17) 0.0473(13) -0.0011(11) 0.0149(12) -0.0100(13) C18 0.0415(16) 0.0476(19) 0.0484(17) 0.0087(14) -0.0070(13) -0.0055(14) C11 0.0472(16) 0.0378(16) 0.0362(14) -0.0050(11) -0.0116(13) 0.0088(13) C19 0.065(2) 0.068(2) 0.0468(17) 0.0085(16) -0.0016(17) -0.0051(17) C12 0.0474(18) 0.059(2) 0.0590(19) -0.0210(16) 0.0033(15) -0.0040(16) C16 0.083(2) 0.050(2) 0.0367(15) -0.0069(14) -0.0041(17) 0.0060(18) C23 0.071(2) 0.069(3) 0.069(2) 0.023(2) 0.0064(19) 0.012(2) C20 0.082(3) 0.093(3) 0.056(2) 0.020(2) -0.003(2) -0.017(2) C15 0.108(3) 0.050(2) 0.049(2) -0.0146(17) -0.022(2) 0.000(2) C21 0.079(3) 0.089(3) 0.074(3) 0.042(2) -0.019(2) -0.015(2) C13 0.056(2) 0.085(3) 0.087(3) -0.017(2) -0.002(2) -0.019(2) C22 0.079(3) 0.064(3) 0.106(3) 0.038(2) -0.004(2) 0.011(2) C14 0.077(3) 0.053(2) 0.090(3) -0.014(2) -0.037(2) -0.0080(19) O3 0.155(3) 0.082(2) 0.098(2) 0.0192(18) 0.048(2) 0.056(2) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 Br2 Cu1 2.3619(5) . ? Cu1 N1 1.942(2) . ? Cu1 N2 2.049(2) . ? Cu1 N4 2.051(2) . ? Cu1 Br1 2.5567(5) . ? N1 C5 1.326(3) . ? N1 C1 1.330(4) . ? C3 C4 1.371(4) . ? C3 C2 1.383(5) . ? C3 H3 0.93 . ? C2 C1 1.378(4) . ? C2 H2 0.93 . ? C5 C4 1.393(4) . ? C5 C6 1.479(4) . ? C8 N4 1.285(4) . ? C8 C9 1.489(4) . ? C8 C1 1.493(4) . ? C9 H9A 0.96 . ? C9 H9B 0.96 . ? C9 H9C 0.96 . ? C7 C6 1.484(4) . ? C7 H7A 0.96 . ? C7 H7B 0.96 . ? C7 H7C 0.96 . ? C4 H4 0.93 . ? C6 N2 1.280(4) . ? N4 N5 1.386(3) . ? N2 N3 1.379(4) . ? N5 C17 1.351(4) . ? N5 H5A 0.78(3) . ? N3 C10 1.383(4) . ? N3 H3A 0.67(3) . ? C17 O2 1.220(4) . ? C17 C18 1.492(4) . ? C10 O1 1.206(4) . ? C10 C11 1.479(4) . ? C18 C19 1.373(5) . ? C18 C23 1.389(5) . ? C11 C12 1.376(5) . ? C11 C16 1.401(4) . ? C19 C20 1.387(5) . ? C19 H19 0.93 . ? C12 C13 1.372(5) . ? C12 H12 0.93 . ? C16 C15 1.375(5) . ? C16 H16 0.93 . ? C23 C22 1.392(5) . ? C23 H23 0.93 . ? C20 C21 1.364(6) . ? C20 H20 0.93 . ? C15 C14 1.358(6) . ? C15 H15 0.93 . ? C21 C22 1.386(6) . ? C21 H21 0.93 . ? C13 C14 1.373(6) . ? C13 H13 0.93 . ? C22 H22 0.93 . ? C14 H14 0.93 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 N2 77.31(9) . . ? N1 Cu1 N4 78.36(10) . . ? N2 Cu1 N4 154.23(10) . . ? N1 Cu1 Br2 153.75(7) . . ? N2 Cu1 Br2 96.73(7) . . ? N4 Cu1 Br2 101.36(7) . . ? N1 Cu1 Br1 99.20(7) . . ? N2 Cu1 Br1 95.09(7) . . ? N4 Cu1 Br1 97.04(7) . . ? Br2 Cu1 Br1 106.833(17) . . ? C5 N1 C1 122.8(2) . . ? C5 N1 Cu1 118.78(19) . . ? C1 N1 Cu1 118.34(19) . . ? C4 C3 C2 121.3(3) . . ? C4 C3 H3 119.3 . . ? C2 C3 H3 119.3 . . ? C1 C2 C3 118.4(3) . . ? C1 C2 H2 120.8 . . ? C3 C2 H2 120.8 . . ? N1 C5 C4 120.2(3) . . ? N1 C5 C6 113.2(3) . . ? C4 C5 C6 126.4(3) . . ? N4 C8 C9 127.3(3) . . ? N4 C8 C1 112.9(2) . . ? C9 C8 C1 119.8(3) . . ? N1 C1 C2 119.7(3) . . ? N1 C1 C8 113.5(2) . . ? C2 C1 C8 126.8(3) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? 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 . . ? C3 C4 C5 117.5(3) . . ? C3 C4 H4 121.3 . . ? C5 C4 H4 121.3 . . ? N2 C6 C5 112.5(2) . . ? N2 C6 C7 127.0(3) . . ? C5 C6 C7 120.2(3) . . ? C8 N4 N5 119.8(2) . . ? C8 N4 Cu1 116.80(19) . . ? N5 N4 Cu1 123.4(2) . . ? C6 N2 N3 120.3(2) . . ? C6 N2 Cu1 117.46(19) . . ? N3 N2 Cu1 122.3(2) . . ? C17 N5 N4 120.6(3) . . ? C17 N5 H5A 116(2) . . ? N4 N5 H5A 115(2) . . ? N2 N3 C10 124.6(3) . . ? N2 N3 H3A 106(3) . . ? C10 N3 H3A 122(3) . . ? O2 C17 N5 120.6(3) . . ? O2 C17 C18 122.7(3) . . ? N5 C17 C18 116.7(3) . . ? O1 C10 N3 122.2(3) . . ? O1 C10 C11 124.5(3) . . ? N3 C10 C11 113.2(3) . . ? C19 C18 C23 119.3(3) . . ? C19 C18 C17 117.4(3) . . ? C23 C18 C17 123.3(3) . . ? C12 C11 C16 117.6(3) . . ? C12 C11 C10 123.6(3) . . ? C16 C11 C10 118.6(3) . . ? C18 C19 C20 120.5(4) . . ? C18 C19 H19 119.7 . . ? C20 C19 H19 119.7 . . ? C13 C12 C11 121.6(3) . . ? C13 C12 H12 119.2 . . ? C11 C12 H12 119.2 . . ? C15 C16 C11 120.4(4) . . ? C15 C16 H16 119.8 . . ? C11 C16 H16 119.8 . . ? C18 C23 C22 120.6(4) . . ? C18 C23 H23 119.7 . . ? C22 C23 H23 119.7 . . ? C21 C20 C19 119.8(4) . . ? C21 C20 H20 120.1 . . ? C19 C20 H20 120.1 . . ? C14 C15 C16 120.5(3) . . ? C14 C15 H15 119.7 . . ? C16 C15 H15 119.7 . . ? C20 C21 C22 121.1(4) . . ? C20 C21 H21 119.4 . . ? C22 C21 H21 119.4 . . ? C12 C13 C14 119.8(4) . . ? C12 C13 H13 120.1 . . ? C14 C13 H13 120.1 . . ? C21 C22 C23 118.6(4) . . ? C21 C22 H22 120.7 . . ? C23 C22 H22 120.7 . . ? C15 C14 C13 120.1(4) . . ? C15 C14 H14 120 . . ? C13 C14 H14 120 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 Cu1 N1 C5 7.6(2) . . . . ? N4 Cu1 N1 C5 179.1(2) . . . . ? Br2 Cu1 N1 C5 87.0(2) . . . . ? Br1 Cu1 N1 C5 -85.5(2) . . . . ? N2 Cu1 N1 C1 -174.4(2) . . . . ? N4 Cu1 N1 C1 -2.9(2) . . . . ? Br2 Cu1 N1 C1 -95.0(2) . . . . ? Br1 Cu1 N1 C1 92.5(2) . . . . ? C4 C3 C2 C1 -1.9(5) . . . . ? C1 N1 C5 C4 -2.1(4) . . . . ? Cu1 N1 C5 C4 175.8(2) . . . . ? C1 N1 C5 C6 173.9(3) . . . . ? Cu1 N1 C5 C6 -8.2(3) . . . . ? C5 N1 C1 C2 0.6(4) . . . . ? Cu1 N1 C1 C2 -177.3(2) . . . . ? C5 N1 C1 C8 -178.6(2) . . . . ? Cu1 N1 C1 C8 3.5(3) . . . . ? C3 C2 C1 N1 1.4(4) . . . . ? C3 C2 C1 C8 -179.6(3) . . . . ? N4 C8 C1 N1 -1.9(4) . . . . ? C9 C8 C1 N1 -179.6(3) . . . . ? N4 C8 C1 C2 179.0(3) . . . . ? C9 C8 C1 C2 1.3(4) . . . . ? C2 C3 C4 C5 0.5(5) . . . . ? N1 C5 C4 C3 1.5(4) . . . . ? C6 C5 C4 C3 -173.9(3) . . . . ? N1 C5 C6 N2 2.8(4) . . . . ? C4 C5 C6 N2 178.5(3) . . . . ? N1 C5 C6 C7 -171.5(3) . . . . ? C4 C5 C6 C7 4.2(5) . . . . ? C9 C8 N4 N5 -3.5(5) . . . . ? C1 C8 N4 N5 179.1(2) . . . . ? C9 C8 N4 Cu1 177.1(2) . . . . ? C1 C8 N4 Cu1 -0.4(3) . . . . ? N1 Cu1 N4 C8 1.7(2) . . . . ? N2 Cu1 N4 C8 21.2(4) . . . . ? Br2 Cu1 N4 C8 154.9(2) . . . . ? Br1 Cu1 N4 C8 -96.3(2) . . . . ? N1 Cu1 N4 N5 -177.7(2) . . . . ? N2 Cu1 N4 N5 -158.3(2) . . . . ? Br2 Cu1 N4 N5 -24.5(2) . . . . ? Br1 Cu1 N4 N5 84.3(2) . . . . ? C5 C6 N2 N3 -175.2(2) . . . . ? C7 C6 N2 N3 -1.3(5) . . . . ? C5 C6 N2 Cu1 3.4(3) . . . . ? C7 C6 N2 Cu1 177.2(3) . . . . ? N1 Cu1 N2 C6 -5.9(2) . . . . ? N4 Cu1 N2 C6 -25.5(4) . . . . ? Br2 Cu1 N2 C6 -160.0(2) . . . . ? Br1 Cu1 N2 C6 92.4(2) . . . . ? N1 Cu1 N2 N3 172.6(2) . . . . ? N4 Cu1 N2 N3 153.0(2) . . . . ? Br2 Cu1 N2 N3 18.5(2) . . . . ? Br1 Cu1 N2 N3 -89.1(2) . . . . ? C8 N4 N5 C17 -69.3(4) . . . . ? Cu1 N4 N5 C17 110.2(3) . . . . ? C6 N2 N3 C10 -59.0(4) . . . . ? Cu1 N2 N3 C10 122.6(3) . . . . ? N4 N5 C17 O2 16.3(4) . . . . ? N4 N5 C17 C18 -162.8(3) . . . . ? N2 N3 C10 O1 3.2(5) . . . . ? N2 N3 C10 C11 -179.5(3) . . . . ? O2 C17 C18 C19 0.2(4) . . . . ? N5 C17 C18 C19 179.3(3) . . . . ? O2 C17 C18 C23 -176.7(3) . . . . ? N5 C17 C18 C23 2.4(5) . . . . ? O1 C10 C11 C12 164.4(3) . . . . ? N3 C10 C11 C12 -12.8(4) . . . . ? O1 C10 C11 C16 -11.4(5) . . . . ? N3 C10 C11 C16 171.3(3) . . . . ? C23 C18 C19 C20 0.5(5) . . . . ? C17 C18 C19 C20 -176.5(3) . . . . ? C16 C11 C12 C13 -1.1(5) . . . . ? C10 C11 C12 C13 -177.0(3) . . . . ? C12 C11 C16 C15 -0.8(5) . . . . ? C10 C11 C16 C15 175.3(3) . . . . ? C19 C18 C23 C22 0.4(6) . . . . ? C17 C18 C23 C22 177.2(4) . . . . ? C18 C19 C20 C21 -0.7(6) . . . . ? C11 C16 C15 C14 2.1(6) . . . . ? C19 C20 C21 C22 -0.1(6) . . . . ? C11 C12 C13 C14 1.7(6) . . . . ? C20 C21 C22 C23 1.0(7) . . . . ? C18 C23 C22 C21 -1.2(7) . . . . ? C16 C15 C14 C13 -1.5(6) . . . . ? C12 C13 C14 C15 -0.4(7) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N5 H5A O3 0.78(3) 2.44(3) 3.176(5) 159(3) 4_466 N3 H3A Br2 0.67(3) 2.78(3) 3.324(3) 141(4) . # END of CIF _database_code_depnum_ccdc_archive 'CCDC 907861' ####################################################################### # # 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_ccg_bf9_0ma _audit_creation_date 2013-05-06T20:48:17-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ? _chemical_name_common 'C52 H52 Cu2 N12 O6' _chemical_formula_moiety 'C52 H52 Cu2 N12 O6' _chemical_formula_sum 'C52 H52 Cu2 N12 O6' _chemical_formula_weight 1068.14 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/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 17.6856(8) _cell_length_b 19.6466(12) _cell_length_c 14.5514(7) _cell_angle_alpha 90 _cell_angle_beta 90.342(3) _cell_angle_gamma 90 _cell_volume 5056.0(5) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4187 _cell_measurement_theta_min 1.55 _cell_measurement_theta_max 26.48 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.15 _exptl_crystal_density_diffrn 1.403 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2216 _exptl_special_details ? #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.904 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6363 _exptl_absorpt_correction_T_max 0.8794 _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BrukerSMART APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_reflns_av_R_equivalents 0.0432 _diffrn_reflns_av_unetI/netI 0.0683 _diffrn_reflns_number 24130 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 26.48 _diffrn_reflns_theta_full 26.48 _diffrn_measured_fraction_theta_full 0.98 _diffrn_measured_fraction_theta_max 0.98 _reflns_number_total 10241 _reflns_number_gt 6487 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'SAINT V7.68A (Bruker AXS, 2009)' _computing_cell_refinement 'APEX2 v2011.2-3 (Bruker AXS, 2009)' _computing_data_reduction 'SAINT/SADABS (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'Pov-Ray for windows Vesion 3.6.2., 2009' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0633P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 10241 _refine_ls_number_parameters 657 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0919 _refine_ls_R_factor_gt 0.0477 _refine_ls_wR_factor_ref 0.1319 _refine_ls_wR_factor_gt 0.1118 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.008 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.469 _refine_diff_density_min -0.35 _refine_diff_density_rms 0.069 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.29621(2) 0.533763(19) 0.10575(3) 0.03767(13) Uani 1 1 d . . . Cu2 Cu 0.20140(2) 0.54891(2) -0.08459(3) 0.03856(13) Uani 1 1 d . . . N6 N 0.14636(14) 0.54175(13) 0.04853(17) 0.0367(6) Uani 1 1 d . . . N10 N 0.19023(16) 0.41499(14) -0.1554(2) 0.0482(7) Uani 1 1 d . . . N9 N 0.16530(15) 0.45693(13) -0.08609(19) 0.0424(7) Uani 1 1 d . . . O4 O 0.25637(13) 0.51276(11) -0.19151(15) 0.0451(6) Uani 1 1 d . . . C40 C 0.23824(19) 0.45040(17) -0.2064(2) 0.0417(8) Uani 1 1 d . . . C27 C 0.0706(2) 0.5865(2) 0.1677(2) 0.0530(9) Uani 1 1 d . . . H27 H 0.0596 0.6223 0.2072 0.064 Uiso 1 1 calc R . . C31 C 0.12082(19) 0.43457(17) -0.0235(2) 0.0443(8) Uani 1 1 d . . . C24 C 0.10174(18) 0.48613(17) 0.0465(2) 0.0400(8) Uani 1 1 d . . . C25 C 0.04142(19) 0.4782(2) 0.1060(2) 0.0519(9) Uani 1 1 d . . . H25 H 0.0124 0.4388 0.1052 0.062 Uiso 1 1 calc R . . C28 C 0.13235(17) 0.59032(17) 0.1107(2) 0.0395(8) Uani 1 1 d . . . C26 C 0.0256(2) 0.5300(2) 0.1660(3) 0.0603(11) Uani 1 1 d . . . H26 H -0.0154 0.5267 0.2053 0.072 Uiso 1 1 calc R . . C32 C 0.0914(2) 0.36393(18) -0.0196(3) 0.0697(12) Uani 1 1 d . . . H32A H 0.0912 0.3447 -0.0803 0.105 Uiso 1 1 calc R . . H32B H 0.0408 0.3644 0.0039 0.105 Uiso 1 1 calc R . . H32C H 0.1231 0.3371 0.02 0.105 Uiso 1 1 calc R . . N1 N 0.35129(14) 0.53611(13) -0.02668(17) 0.0360(6) Uani 1 1 d . . . N2 N 0.32190(15) 0.43949(13) 0.08859(19) 0.0415(7) Uani 1 1 d . . . N3 N 0.29044(16) 0.39254(13) 0.1469(2) 0.0470(7) Uani 1 1 d . . . O1 O 0.23528(12) 0.49048(11) 0.20353(14) 0.0424(5) Uani 1 1 d . . . C10 C 0.24529(18) 0.42611(17) 0.2046(2) 0.0407(8) Uani 1 1 d . . . C5 C 0.38998(18) 0.47710(17) -0.0357(2) 0.0403(8) Uani 1 1 d . . . C1 C 0.37128(17) 0.58971(16) -0.0790(2) 0.0386(8) Uani 1 1 d . . . C6 C 0.36452(19) 0.42066(17) 0.0221(2) 0.0428(8) Uani 1 1 d . . . C3 C 0.4721(2) 0.5269(2) -0.1452(2) 0.0574(10) Uani 1 1 d . . . H3 H 0.5134 0.5241 -0.1844 0.069 Uiso 1 1 calc R . . C11 C 0.20456(19) 0.38461(17) 0.2743(2) 0.0417(8) Uani 1 1 d . . . C4 C 0.45015(19) 0.47071(19) -0.0952(2) 0.0488(9) Uani 1 1 d . . . H4 H 0.4753 0.4294 -0.1013 0.059 Uiso 1 1 calc R . . C2 C 0.43330(19) 0.5866(2) -0.1371(2) 0.0505(9) Uani 1 1 d . . . H2 H 0.4482 0.6248 -0.1702 0.061 Uiso 1 1 calc R . . C8 C 0.32209(17) 0.64987(16) -0.0819(2) 0.0367(7) Uani 1 1 d . . . C29 C 0.18825(17) 0.64512(16) 0.1230(2) 0.0374(7) Uani 1 1 d . . . N7 N 0.25832(14) 0.62707(12) 0.12111(16) 0.0352(6) Uani 1 1 d . . . N4 N 0.24968(14) 0.63869(13) -0.08353(17) 0.0370(6) Uani 1 1 d . . . N8 N 0.31158(14) 0.67714(13) 0.13805(18) 0.0385(6) Uani 1 1 d . . . N5 N 0.20320(14) 0.69481(13) -0.09099(18) 0.0408(7) Uani 1 1 d . . . C33 C 0.37822(17) 0.64912(16) 0.1569(2) 0.0351(7) Uani 1 1 d . . . O3 O 0.39299(12) 0.58604(11) 0.16006(15) 0.0425(5) Uani 1 1 d . . . O2 O 0.11054(12) 0.61502(11) -0.12339(16) 0.0492(6) Uani 1 1 d . . . C46 C 0.3324(2) 0.44506(19) -0.3312(3) 0.0564(10) Uani 1 1 d . . . H46 H 0.3548 0.4842 -0.3075 0.068 Uiso 1 1 calc R . . C41 C 0.27125(19) 0.41621(17) -0.2872(2) 0.0429(8) Uani 1 1 d . . . C42 C 0.2404(2) 0.3567(2) -0.3222(3) 0.0573(10) Uani 1 1 d . . . H42 H 0.2004 0.3359 -0.2921 0.069 Uiso 1 1 calc R . . C48 C 0.3058(3) 0.5972(2) 0.3665(3) 0.0761(13) Uani 1 1 d . . . H48A H 0.3203 0.6386 0.3363 0.114 Uiso 1 1 calc R . . H48B H 0.2742 0.6077 0.4179 0.114 Uiso 1 1 calc R . . H48C H 0.2785 0.5688 0.3241 0.114 Uiso 1 1 calc R . . C30 C 0.1640(2) 0.71586(17) 0.1456(3) 0.0569(10) Uani 1 1 d . . . H30A H 0.1763 0.7257 0.2085 0.085 Uiso 1 1 calc R . . H30B H 0.1104 0.72 0.1365 0.085 Uiso 1 1 calc R . . H30C H 0.1896 0.7474 0.1062 0.085 Uiso 1 1 calc R . . C34 C 0.43969(17) 0.69872(17) 0.1782(2) 0.0386(8) Uani 1 1 d . . . C35 C 0.50182(19) 0.67850(19) 0.2292(2) 0.0511(9) Uani 1 1 d . . . H35 H 0.5049 0.6341 0.2512 0.061 Uiso 1 1 calc R . . C43 C 0.2687(3) 0.3283(2) -0.4010(3) 0.0770(13) Uani 1 1 d . . . H43 H 0.2471 0.2887 -0.4245 0.092 Uiso 1 1 calc R . . C39 C 0.4362(2) 0.76594(18) 0.1481(2) 0.0495(9) Uani 1 1 d . . . H39 H 0.3941 0.781 0.1153 0.059 Uiso 1 1 calc R . . C38 C 0.4947(2) 0.8105(2) 0.1667(3) 0.0605(10) Uani 1 1 d . . . H38 H 0.4926 0.8548 0.1444 0.073 Uiso 1 1 calc R . . C37 C 0.5559(2) 0.7899(2) 0.2176(3) 0.0646(11) Uani 1 1 d . . . H37 H 0.5946 0.8203 0.2315 0.078 Uiso 1 1 calc R . . C23 C 0.01049(19) 0.72093(19) -0.1681(2) 0.0525(9) Uani 1 1 d . . . H23 H 0.0009 0.6784 -0.1935 0.063 Uiso 1 1 calc R . . C19 C 0.0903(2) 0.79627(19) -0.0848(2) 0.0556(10) Uani 1 1 d . . . H19 H 0.1354 0.8051 -0.0538 0.067 Uiso 1 1 calc R . . C18 C 0.07783(18) 0.73234(17) -0.1211(2) 0.0410(8) Uani 1 1 d . . . C16 C 0.2242(2) 0.31800(17) 0.2923(2) 0.0516(9) Uani 1 1 d . . . H16 H 0.2633 0.2977 0.2598 0.062 Uiso 1 1 calc R . . C12 C 0.1461(2) 0.41368(19) 0.3216(3) 0.0573(10) Uani 1 1 d . . . H12 H 0.1325 0.4586 0.3099 0.069 Uiso 1 1 calc R . . C14 C 0.1284(3) 0.3110(2) 0.4054(3) 0.0685(12) Uani 1 1 d . . . H14 H 0.1033 0.2866 0.4506 0.082 Uiso 1 1 calc R . . C15 C 0.1862(2) 0.2814(2) 0.3580(3) 0.0631(11) Uani 1 1 d . . . H15 H 0.1997 0.2365 0.3701 0.076 Uiso 1 1 calc R . . C13 C 0.1074(3) 0.3767(2) 0.3862(3) 0.0728(12) Uani 1 1 d . . . H13 H 0.067 0.3963 0.417 0.087 Uiso 1 1 calc R . . C36 C 0.5594(2) 0.7241(2) 0.2476(3) 0.0671(12) Uani 1 1 d . . . H36 H 0.6014 0.7097 0.2811 0.08 Uiso 1 1 calc R . . C20 C 0.0371(2) 0.8473(2) -0.0936(3) 0.0642(11) Uani 1 1 d . . . H20 H 0.0465 0.89 -0.0686 0.077 Uiso 1 1 calc R . . C22 C -0.0421(2) 0.7721(2) -0.1774(3) 0.0659(11) Uani 1 1 d . . . H22 H -0.0867 0.764 -0.2099 0.079 Uiso 1 1 calc R . . C21 C -0.0296(2) 0.8351(2) -0.1391(3) 0.0654(11) Uani 1 1 d . . . H21 H -0.0659 0.8691 -0.1441 0.078 Uiso 1 1 calc R . . C44 C 0.3284(3) 0.3575(3) -0.4452(3) 0.0794(14) Uani 1 1 d . . . H44 H 0.3474 0.338 -0.4985 0.095 Uiso 1 1 calc R . . C45 C 0.3602(3) 0.4159(2) -0.4105(3) 0.0758(13) Uani 1 1 d . . . H45 H 0.4008 0.4359 -0.4405 0.091 Uiso 1 1 calc R . . C7 C 0.3862(3) 0.34814(19) 0.0047(3) 0.0741(13) Uani 1 1 d . . . H7A H 0.3673 0.32 0.0532 0.111 Uiso 1 1 calc R . . H7B H 0.4403 0.3445 0.0025 0.111 Uiso 1 1 calc R . . H7C H 0.365 0.3335 -0.0529 0.111 Uiso 1 1 calc R . . C49 C 0.4200(3) 0.5942(2) 0.4675(3) 0.0972(17) Uani 1 1 d . . . H49A H 0.4534 0.5611 0.4942 0.146 Uiso 1 1 calc R . . H49B H 0.3886 0.6133 0.5144 0.146 Uiso 1 1 calc R . . H49C H 0.4492 0.6297 0.4395 0.146 Uiso 1 1 calc R . . N11 N 0.3728(2) 0.56174(17) 0.3983(2) 0.0615(9) Uani 1 1 d . . . C47 C 0.3955(3) 0.5050(2) 0.3590(3) 0.0792(14) Uani 1 1 d . . . H47 H 0.3637 0.4859 0.3149 0.095 Uiso 1 1 calc R . . C51 C 0.2222(4) 0.6046(3) 0.6251(4) 0.121(2) Uani 1 1 d . . . H51C H 0.2113 0.6297 0.6799 0.181 Uiso 1 1 calc R . . H51B H 0.2285 0.6355 0.5747 0.181 Uiso 1 1 calc R . . H51A H 0.268 0.579 0.6339 0.181 Uiso 1 1 calc R . . C50 C 0.1023(6) 0.5524(4) 0.6541(5) 0.149(3) Uani 1 1 d . . . H50 H 0.0963 0.5801 0.7053 0.178 Uiso 1 1 calc R . . C52 C 0.1700(4) 0.5130(3) 0.5282(4) 0.135(2) Uani 1 1 d . . . H52B H 0.1277 0.4825 0.5245 0.203 Uiso 1 1 calc R . . H52A H 0.2157 0.4873 0.5362 0.203 Uiso 1 1 calc R . . H52C H 0.1729 0.539 0.4725 0.203 Uiso 1 1 calc R . . O5 O 0.4548(2) 0.47503(18) 0.3753(2) 0.1063(12) Uani 1 1 d . . . C17 C 0.13311(18) 0.67556(17) -0.1114(2) 0.0397(8) Uani 1 1 d . . . N12 N 0.1604(3) 0.5583(2) 0.6051(3) 0.0955(15) Uani 1 1 d . . . O6 O 0.0507(4) 0.5074(3) 0.6332(4) 0.188(3) Uani 1 1 d . . . C9 C 0.3546(2) 0.71963(17) -0.0914(3) 0.0568(10) Uani 1 1 d . . . H9A H 0.352 0.7336 -0.1545 0.085 Uiso 1 1 calc R . . H9B H 0.4065 0.7193 -0.0714 0.085 Uiso 1 1 calc R . . H9C H 0.3264 0.7509 -0.0543 0.085 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0321(2) 0.0340(2) 0.0469(2) 0.00114(17) 0.00517(18) 0.00053(18) Cu2 0.0316(2) 0.0353(2) 0.0489(2) 0.00056(18) 0.00388(18) -0.00578(18) N6 0.0270(14) 0.0403(16) 0.0429(15) 0.0060(12) 0.0065(12) -0.0019(12) N10 0.0465(18) 0.0402(17) 0.0581(19) -0.0085(14) 0.0107(15) -0.0089(14) N9 0.0346(15) 0.0403(16) 0.0524(17) -0.0016(13) 0.0050(13) -0.0024(13) O4 0.0472(14) 0.0409(13) 0.0473(13) -0.0020(11) 0.0062(11) -0.0103(11) C40 0.0372(19) 0.042(2) 0.0453(19) -0.0001(16) -0.0022(15) -0.0038(16) C27 0.038(2) 0.064(3) 0.057(2) -0.0103(19) 0.0148(18) 0.0023(19) C31 0.038(2) 0.0392(19) 0.056(2) 0.0068(16) 0.0075(17) -0.0058(16) C24 0.0308(18) 0.0431(19) 0.0463(19) 0.0076(15) 0.0033(15) -0.0018(15) C25 0.038(2) 0.060(2) 0.059(2) 0.012(2) 0.0062(18) -0.0086(18) C28 0.0266(17) 0.046(2) 0.0458(19) -0.0016(16) 0.0036(15) 0.0025(15) C26 0.034(2) 0.084(3) 0.063(2) 0.004(2) 0.0205(18) -0.007(2) C32 0.078(3) 0.042(2) 0.089(3) -0.001(2) 0.026(2) -0.015(2) N1 0.0298(14) 0.0395(15) 0.0388(14) -0.0004(12) 0.0042(11) -0.0002(12) N2 0.0401(16) 0.0375(16) 0.0471(17) 0.0009(13) 0.0051(14) -0.0017(13) N3 0.0505(18) 0.0342(15) 0.0566(18) 0.0067(14) 0.0101(15) -0.0010(14) O1 0.0470(14) 0.0317(12) 0.0484(13) 0.0037(10) 0.0084(11) 0.0001(11) C10 0.0379(19) 0.0377(19) 0.047(2) 0.0024(15) -0.0031(16) 0.0022(16) C5 0.0357(19) 0.047(2) 0.0382(18) -0.0049(15) 0.0013(15) 0.0046(16) C1 0.0300(17) 0.046(2) 0.0399(18) 0.0025(15) 0.0026(14) -0.0066(15) C6 0.045(2) 0.0373(19) 0.047(2) -0.0055(16) 0.0087(17) 0.0018(16) C3 0.035(2) 0.083(3) 0.054(2) -0.001(2) 0.0146(18) 0.003(2) C11 0.045(2) 0.0395(19) 0.0408(19) 0.0019(15) -0.0014(16) -0.0078(16) C4 0.037(2) 0.058(2) 0.052(2) -0.0017(18) 0.0074(17) 0.0064(18) C2 0.0345(19) 0.064(2) 0.053(2) 0.0113(19) 0.0108(17) -0.0063(18) C8 0.0326(18) 0.0399(18) 0.0376(17) 0.0035(14) 0.0059(14) -0.0071(15) C29 0.0316(18) 0.0391(18) 0.0415(18) -0.0006(14) 0.0063(14) 0.0034(15) N7 0.0330(15) 0.0346(15) 0.0380(14) 0.0052(11) 0.0027(12) -0.0028(12) N4 0.0311(14) 0.0388(15) 0.0410(15) 0.0034(12) 0.0025(12) -0.0021(12) N8 0.0299(14) 0.0331(15) 0.0524(16) -0.0026(12) 0.0030(12) -0.0024(12) N5 0.0320(15) 0.0345(15) 0.0560(17) 0.0031(13) 0.0008(13) 0.0003(13) C33 0.0328(18) 0.0395(19) 0.0330(17) -0.0033(14) 0.0046(14) -0.0031(15) O3 0.0333(12) 0.0383(13) 0.0559(14) -0.0035(11) 0.0006(11) 0.0044(10) O2 0.0330(13) 0.0406(14) 0.0739(16) 0.0040(12) -0.0063(12) -0.0073(11) C46 0.053(2) 0.057(2) 0.060(2) 0.0017(19) 0.0119(19) 0.004(2) C41 0.040(2) 0.045(2) 0.0439(19) -0.0025(16) -0.0017(16) 0.0004(16) C42 0.047(2) 0.065(3) 0.060(2) -0.013(2) -0.0056(19) -0.003(2) C48 0.082(3) 0.085(3) 0.062(3) -0.012(2) -0.003(2) 0.010(3) C30 0.045(2) 0.050(2) 0.076(3) -0.0079(19) 0.0053(19) 0.0094(18) C34 0.0321(17) 0.047(2) 0.0370(17) -0.0038(15) 0.0045(14) -0.0034(15) C35 0.044(2) 0.050(2) 0.059(2) -0.0047(18) -0.0067(18) 0.0026(18) C43 0.076(3) 0.089(3) 0.065(3) -0.029(3) -0.013(2) 0.005(3) C39 0.048(2) 0.047(2) 0.052(2) -0.0004(17) -0.0084(17) -0.0092(18) C38 0.065(3) 0.050(2) 0.067(2) -0.0004(19) 0.001(2) -0.017(2) C37 0.047(2) 0.068(3) 0.079(3) -0.014(2) -0.004(2) -0.021(2) C23 0.037(2) 0.056(2) 0.064(2) 0.0051(19) -0.0017(18) 0.0003(18) C19 0.049(2) 0.055(2) 0.062(2) -0.0014(19) -0.0049(19) 0.0050(19) C18 0.0345(18) 0.046(2) 0.0423(19) 0.0088(16) 0.0069(15) -0.0020(16) C16 0.051(2) 0.043(2) 0.061(2) 0.0079(18) 0.0072(19) 0.0018(18) C12 0.068(3) 0.044(2) 0.059(2) 0.0084(18) 0.018(2) 0.004(2) C14 0.094(3) 0.056(3) 0.056(2) 0.008(2) 0.020(2) -0.015(2) C15 0.082(3) 0.045(2) 0.062(2) 0.015(2) 0.005(2) -0.004(2) C13 0.081(3) 0.064(3) 0.073(3) 0.008(2) 0.034(2) 0.000(2) C36 0.042(2) 0.076(3) 0.084(3) -0.012(2) -0.019(2) -0.003(2) C20 0.066(3) 0.051(2) 0.075(3) -0.005(2) 0.002(2) 0.009(2) C22 0.038(2) 0.079(3) 0.081(3) 0.008(2) -0.004(2) 0.012(2) C21 0.050(2) 0.070(3) 0.076(3) 0.013(2) 0.014(2) 0.022(2) C44 0.098(4) 0.090(4) 0.050(3) -0.015(2) 0.005(3) 0.023(3) C45 0.072(3) 0.084(3) 0.071(3) 0.004(3) 0.022(2) 0.014(3) C7 0.091(3) 0.049(2) 0.082(3) -0.005(2) 0.028(3) 0.012(2) C49 0.093(4) 0.094(4) 0.105(4) -0.032(3) -0.023(3) 0.001(3) N11 0.072(2) 0.061(2) 0.0512(19) -0.0085(16) -0.0028(17) 0.0052(19) C47 0.110(4) 0.071(3) 0.056(3) -0.007(2) -0.008(3) 0.017(3) C51 0.182(7) 0.063(3) 0.118(5) 0.006(3) -0.024(5) 0.004(4) C50 0.197(10) 0.159(8) 0.090(5) 0.000(5) 0.021(6) 0.014(7) C52 0.192(7) 0.111(5) 0.104(5) -0.021(4) 0.015(5) 0.020(5) O5 0.129(3) 0.099(3) 0.091(2) -0.015(2) -0.013(2) 0.046(2) C17 0.0348(18) 0.043(2) 0.0411(18) 0.0068(15) 0.0040(15) -0.0016(16) N12 0.136(4) 0.095(3) 0.056(2) 0.014(2) 0.022(3) 0.023(3) O6 0.192(7) 0.173(6) 0.198(6) 0.043(5) 0.042(5) -0.006(5) C9 0.043(2) 0.046(2) 0.082(3) 0.0104(19) 0.0059(19) -0.0162(18) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N2 1.924(3) . ? Cu1 N7 1.965(3) . ? Cu1 O1 1.982(2) . ? Cu1 O3 2.143(2) . ? Cu1 N1 2.165(3) . ? Cu2 N9 1.917(3) . ? Cu2 N4 1.960(3) . ? Cu2 O4 1.972(2) . ? Cu2 O2 2.139(2) . ? Cu2 N6 2.178(3) . ? N6 C28 1.339(4) . ? N6 C24 1.348(4) . ? N10 C40 1.327(4) . ? N10 N9 1.377(4) . ? N9 C31 1.284(4) . ? O4 C40 1.284(4) . ? C40 C41 1.478(5) . ? C27 C26 1.365(5) . ? C27 C28 1.378(4) . ? C27 H27 0.93 . ? C31 C24 1.477(5) . ? C31 C32 1.483(5) . ? C24 C25 1.386(4) . ? C25 C26 1.371(5) . ? C25 H25 0.93 . ? C28 C29 1.472(4) . ? C26 H26 0.93 . ? C32 H32A 0.96 . ? C32 H32B 0.96 . ? C32 H32C 0.96 . ? N1 C1 1.348(4) . ? N1 C5 1.353(4) . ? N2 C6 1.285(4) . ? N2 N3 1.373(4) . ? N3 C10 1.336(4) . ? O1 C10 1.277(4) . ? C10 C11 1.491(4) . ? C5 C4 1.382(4) . ? C5 C6 1.464(5) . ? C1 C2 1.390(4) . ? C1 C8 1.468(4) . ? C6 C7 1.497(5) . ? C3 C2 1.365(5) . ? C3 C4 1.380(5) . ? C3 H3 0.93 . ? C11 C12 1.370(5) . ? C11 C16 1.378(4) . ? C4 H4 0.93 . ? C2 H2 0.93 . ? C8 N4 1.299(4) . ? C8 C9 1.493(4) . ? C29 N7 1.289(4) . ? C29 C30 1.492(4) . ? N7 N8 1.383(3) . ? N4 N5 1.379(3) . ? N8 C33 1.328(4) . ? N5 C17 1.328(4) . ? C33 O3 1.267(4) . ? C33 C34 1.491(4) . ? O2 C17 1.266(4) . ? C46 C45 1.381(5) . ? C46 C41 1.382(5) . ? C46 H46 0.93 . ? C41 C42 1.385(5) . ? C42 C43 1.373(5) . ? C42 H42 0.93 . ? C48 N11 1.449(5) . ? C48 H48A 0.96 . ? C48 H48B 0.96 . ? C48 H48C 0.96 . ? C30 H30A 0.96 . ? C30 H30B 0.96 . ? C30 H30C 0.96 . ? C34 C35 1.381(4) . ? C34 C39 1.392(4) . ? C35 C36 1.380(5) . ? C35 H35 0.93 . ? C43 C44 1.366(6) . ? C43 H43 0.93 . ? C39 C38 1.381(5) . ? C39 H39 0.93 . ? C38 C37 1.368(5) . ? C38 H38 0.93 . ? C37 C36 1.366(5) . ? C37 H37 0.93 . ? C23 C22 1.377(5) . ? C23 C18 1.388(5) . ? C23 H23 0.93 . ? C19 C18 1.380(5) . ? C19 C20 1.381(5) . ? C19 H19 0.93 . ? C18 C17 1.490(4) . ? C16 C15 1.375(5) . ? C16 H16 0.93 . ? C12 C13 1.373(5) . ? C12 H12 0.93 . ? C14 C15 1.367(5) . ? C14 C13 1.371(5) . ? C14 H14 0.93 . ? C15 H15 0.93 . ? C13 H13 0.93 . ? C36 H36 0.93 . ? C20 C21 1.369(5) . ? C20 H20 0.93 . ? C22 C21 1.374(6) . ? C22 H22 0.93 . ? C21 H21 0.93 . ? C44 C45 1.372(6) . ? C44 H44 0.93 . ? C45 H45 0.93 . ? C7 H7A 0.96 . ? C7 H7B 0.96 . ? C7 H7C 0.96 . ? C49 N11 1.450(5) . ? C49 H49A 0.96 . ? C49 H49B 0.96 . ? C49 H49C 0.96 . ? N11 C47 1.317(5) . ? C47 O5 1.225(5) . ? C47 H47 0.93 . ? C51 N12 1.450(7) . ? C51 H51C 0.96 . ? C51 H51B 0.96 . ? C51 H51A 0.96 . ? C50 N12 1.258(9) . ? C50 O6 1.305(9) . ? C50 H50 0.93 . ? C52 N12 1.441(6) . ? C52 H52B 0.96 . ? C52 H52A 0.96 . ? C52 H52C 0.96 . ? C9 H9A 0.96 . ? C9 H9B 0.96 . ? C9 H9C 0.96 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Cu1 N7 173.69(11) . . ? N2 Cu1 O1 79.04(10) . . ? N7 Cu1 O1 97.55(9) . . ? N2 Cu1 O3 108.70(10) . . ? N7 Cu1 O3 77.47(9) . . ? O1 Cu1 O3 112.17(9) . . ? N2 Cu1 N1 78.29(11) . . ? N7 Cu1 N1 103.71(10) . . ? O1 Cu1 N1 153.86(9) . . ? O3 Cu1 N1 87.45(9) . . ? N9 Cu2 N4 173.62(11) . . ? N9 Cu2 O4 79.47(11) . . ? N4 Cu2 O4 96.52(10) . . ? N9 Cu2 O2 108.65(10) . . ? N4 Cu2 O2 77.42(9) . . ? O4 Cu2 O2 112.55(9) . . ? N9 Cu2 N6 78.38(11) . . ? N4 Cu2 N6 104.37(10) . . ? O4 Cu2 N6 154.65(10) . . ? O2 Cu2 N6 86.27(9) . . ? C28 N6 C24 118.8(3) . . ? C28 N6 Cu2 129.8(2) . . ? C24 N6 Cu2 107.3(2) . . ? C40 N10 N9 107.7(3) . . ? C31 N9 N10 121.0(3) . . ? C31 N9 Cu2 121.3(2) . . ? N10 N9 Cu2 117.7(2) . . ? C40 O4 Cu2 110.6(2) . . ? O4 C40 N10 124.5(3) . . ? O4 C40 C41 117.9(3) . . ? N10 C40 C41 117.6(3) . . ? C26 C27 C28 119.8(3) . . ? C26 C27 H27 120.1 . . ? C28 C27 H27 120.1 . . ? N9 C31 C24 113.4(3) . . ? N9 C31 C32 124.3(3) . . ? C24 C31 C32 122.3(3) . . ? N6 C24 C25 122.0(3) . . ? N6 C24 C31 115.8(3) . . ? C25 C24 C31 122.2(3) . . ? C26 C25 C24 118.3(3) . . ? C26 C25 H25 120.8 . . ? C24 C25 H25 120.8 . . ? N6 C28 C27 121.2(3) . . ? N6 C28 C29 118.5(3) . . ? C27 C28 C29 120.1(3) . . ? C27 C26 C25 119.6(3) . . ? C27 C26 H26 120.2 . . ? C25 C26 H26 120.2 . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C1 N1 C5 118.7(3) . . ? C1 N1 Cu1 129.8(2) . . ? C5 N1 Cu1 107.4(2) . . ? C6 N2 N3 120.9(3) . . ? C6 N2 Cu1 121.0(2) . . ? N3 N2 Cu1 118.0(2) . . ? C10 N3 N2 107.6(3) . . ? C10 O1 Cu1 111.0(2) . . ? O1 C10 N3 124.4(3) . . ? O1 C10 C11 118.8(3) . . ? N3 C10 C11 116.8(3) . . ? N1 C5 C4 122.0(3) . . ? N1 C5 C6 115.9(3) . . ? C4 C5 C6 122.1(3) . . ? N1 C1 C2 121.3(3) . . ? N1 C1 C8 119.2(3) . . ? C2 C1 C8 119.2(3) . . ? N2 C6 C5 113.5(3) . . ? N2 C6 C7 123.6(3) . . ? C5 C6 C7 122.9(3) . . ? C2 C3 C4 119.9(3) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C12 C11 C16 119.4(3) . . ? C12 C11 C10 118.9(3) . . ? C16 C11 C10 121.8(3) . . ? C3 C4 C5 118.6(3) . . ? C3 C4 H4 120.7 . . ? C5 C4 H4 120.7 . . ? C3 C2 C1 119.3(3) . . ? C3 C2 H2 120.3 . . ? C1 C2 H2 120.3 . . ? N4 C8 C1 116.6(3) . . ? N4 C8 C9 122.3(3) . . ? C1 C8 C9 120.9(3) . . ? N7 C29 C28 116.2(3) . . ? N7 C29 C30 122.6(3) . . ? C28 C29 C30 121.0(3) . . ? C29 N7 N8 117.0(3) . . ? C29 N7 Cu1 126.0(2) . . ? N8 N7 Cu1 116.83(19) . . ? C8 N4 N5 117.0(3) . . ? C8 N4 Cu2 125.6(2) . . ? N5 N4 Cu2 117.35(18) . . ? C33 N8 N7 110.2(2) . . ? C17 N5 N4 110.2(3) . . ? O3 C33 N8 126.5(3) . . ? O3 C33 C34 118.8(3) . . ? N8 C33 C34 114.7(3) . . ? C33 O3 Cu1 106.93(18) . . ? C17 O2 Cu2 107.35(19) . . ? C45 C46 C41 120.0(4) . . ? C45 C46 H46 120 . . ? C41 C46 H46 120 . . ? C46 C41 C42 118.9(3) . . ? C46 C41 C40 119.8(3) . . ? C42 C41 C40 121.3(3) . . ? C43 C42 C41 120.4(4) . . ? C43 C42 H42 119.8 . . ? C41 C42 H42 119.8 . . ? N11 C48 H48A 109.5 . . ? N11 C48 H48B 109.5 . . ? H48A C48 H48B 109.5 . . ? N11 C48 H48C 109.5 . . ? H48A C48 H48C 109.5 . . ? H48B C48 H48C 109.5 . . ? C29 C30 H30A 109.5 . . ? C29 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C29 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C35 C34 C39 118.4(3) . . ? C35 C34 C33 120.0(3) . . ? C39 C34 C33 121.6(3) . . ? C36 C35 C34 120.1(4) . . ? C36 C35 H35 120 . . ? C34 C35 H35 120 . . ? C44 C43 C42 120.5(4) . . ? C44 C43 H43 119.7 . . ? C42 C43 H43 119.7 . . ? C38 C39 C34 120.5(3) . . ? C38 C39 H39 119.7 . . ? C34 C39 H39 119.7 . . ? C37 C38 C39 120.5(4) . . ? C37 C38 H38 119.8 . . ? C39 C38 H38 119.8 . . ? C36 C37 C38 119.2(4) . . ? C36 C37 H37 120.4 . . ? C38 C37 H37 120.4 . . ? C22 C23 C18 120.6(4) . . ? C22 C23 H23 119.7 . . ? C18 C23 H23 119.7 . . ? C18 C19 C20 121.2(4) . . ? C18 C19 H19 119.4 . . ? C20 C19 H19 119.4 . . ? C19 C18 C23 118.1(3) . . ? C19 C18 C17 122.8(3) . . ? C23 C18 C17 119.1(3) . . ? C15 C16 C11 120.3(4) . . ? C15 C16 H16 119.8 . . ? C11 C16 H16 119.8 . . ? C11 C12 C13 120.3(4) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? C15 C14 C13 120.0(4) . . ? C15 C14 H14 120 . . ? C13 C14 H14 120 . . ? C14 C15 C16 119.8(4) . . ? C14 C15 H15 120.1 . . ? C16 C15 H15 120.1 . . ? C14 C13 C12 120.1(4) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C37 C36 C35 121.3(4) . . ? C37 C36 H36 119.3 . . ? C35 C36 H36 119.3 . . ? C21 C20 C19 120.1(4) . . ? C21 C20 H20 119.9 . . ? C19 C20 H20 119.9 . . ? C21 C22 C23 120.7(4) . . ? C21 C22 H22 119.7 . . ? C23 C22 H22 119.7 . . ? C20 C21 C22 119.4(4) . . ? C20 C21 H21 120.3 . . ? C22 C21 H21 120.3 . . ? C43 C44 C45 119.6(4) . . ? C43 C44 H44 120.2 . . ? C45 C44 H44 120.2 . . ? C44 C45 C46 120.5(4) . . ? C44 C45 H45 119.8 . . ? C46 C45 H45 119.8 . . ? 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 . . ? N11 C49 H49A 109.5 . . ? N11 C49 H49B 109.5 . . ? H49A C49 H49B 109.5 . . ? N11 C49 H49C 109.5 . . ? H49A C49 H49C 109.5 . . ? H49B C49 H49C 109.5 . . ? C47 N11 C48 121.3(4) . . ? C47 N11 C49 119.9(4) . . ? C48 N11 C49 118.4(3) . . ? O5 C47 N11 125.8(5) . . ? O5 C47 H47 117.1 . . ? N11 C47 H47 117.1 . . ? N12 C51 H51C 109.5 . . ? N12 C51 H51B 109.5 . . ? H51C C51 H51B 109.5 . . ? N12 C51 H51A 109.5 . . ? H51C C51 H51A 109.5 . . ? H51B C51 H51A 109.5 . . ? N12 C50 O6 120.2(8) . . ? N12 C50 H50 119.9 . . ? O6 C50 H50 119.9 . . ? N12 C52 H52B 109.5 . . ? N12 C52 H52A 109.5 . . ? H52B C52 H52A 109.5 . . ? N12 C52 H52C 109.5 . . ? H52B C52 H52C 109.5 . . ? H52A C52 H52C 109.5 . . ? O2 C17 N5 126.3(3) . . ? O2 C17 C18 119.0(3) . . ? N5 C17 C18 114.8(3) . . ? C50 N12 C52 118.9(7) . . ? C50 N12 C51 124.2(6) . . ? C52 N12 C51 116.8(5) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N9 Cu2 N6 C28 -172.4(3) . . . . ? N4 Cu2 N6 C28 13.5(3) . . . . ? O4 Cu2 N6 C28 158.1(2) . . . . ? O2 Cu2 N6 C28 -62.4(3) . . . . ? N9 Cu2 N6 C24 -15.9(2) . . . . ? N4 Cu2 N6 C24 170.03(19) . . . . ? O4 Cu2 N6 C24 -45.4(3) . . . . ? O2 Cu2 N6 C24 94.0(2) . . . . ? C40 N10 N9 C31 -176.5(3) . . . . ? C40 N10 N9 Cu2 1.9(3) . . . . ? N4 Cu2 N9 C31 125.0(10) . . . . ? O4 Cu2 N9 C31 176.4(3) . . . . ? O2 Cu2 N9 C31 -73.2(3) . . . . ? N6 Cu2 N9 C31 8.8(3) . . . . ? N4 Cu2 N9 N10 -53.4(11) . . . . ? O4 Cu2 N9 N10 -2.0(2) . . . . ? O2 Cu2 N9 N10 108.4(2) . . . . ? N6 Cu2 N9 N10 -169.6(2) . . . . ? N9 Cu2 O4 C40 1.7(2) . . . . ? N4 Cu2 O4 C40 176.7(2) . . . . ? O2 Cu2 O4 C40 -104.3(2) . . . . ? N6 Cu2 O4 C40 31.1(3) . . . . ? Cu2 O4 C40 N10 -1.3(4) . . . . ? Cu2 O4 C40 C41 176.9(2) . . . . ? N9 N10 C40 O4 -0.3(4) . . . . ? N9 N10 C40 C41 -178.5(3) . . . . ? N10 N9 C31 C24 178.4(3) . . . . ? Cu2 N9 C31 C24 0.1(4) . . . . ? N10 N9 C31 C32 -0.9(5) . . . . ? Cu2 N9 C31 C32 -179.3(3) . . . . ? C28 N6 C24 C25 0.8(4) . . . . ? Cu2 N6 C24 C25 -158.7(3) . . . . ? C28 N6 C24 C31 -179.7(3) . . . . ? Cu2 N6 C24 C31 20.8(3) . . . . ? N9 C31 C24 N6 -15.6(4) . . . . ? C32 C31 C24 N6 163.7(3) . . . . ? N9 C31 C24 C25 163.9(3) . . . . ? C32 C31 C24 C25 -16.8(5) . . . . ? N6 C24 C25 C26 2.4(5) . . . . ? C31 C24 C25 C26 -177.0(3) . . . . ? C24 N6 C28 C27 -4.5(5) . . . . ? Cu2 N6 C28 C27 149.8(3) . . . . ? C24 N6 C28 C29 169.9(3) . . . . ? Cu2 N6 C28 C29 -35.8(4) . . . . ? C26 C27 C28 N6 4.8(5) . . . . ? C26 C27 C28 C29 -169.5(3) . . . . ? C28 C27 C26 C25 -1.5(6) . . . . ? C24 C25 C26 C27 -2.0(6) . . . . ? N2 Cu1 N1 C1 -172.6(3) . . . . ? N7 Cu1 N1 C1 13.5(3) . . . . ? O1 Cu1 N1 C1 157.0(2) . . . . ? O3 Cu1 N1 C1 -62.9(3) . . . . ? N2 Cu1 N1 C5 -16.30(19) . . . . ? N7 Cu1 N1 C5 169.83(19) . . . . ? O1 Cu1 N1 C5 -46.7(3) . . . . ? O3 Cu1 N1 C5 93.4(2) . . . . ? N7 Cu1 N2 C6 118.1(10) . . . . ? O1 Cu1 N2 C6 175.8(3) . . . . ? O3 Cu1 N2 C6 -74.3(3) . . . . ? N1 Cu1 N2 C6 8.9(2) . . . . ? N7 Cu1 N2 N3 -58.8(11) . . . . ? O1 Cu1 N2 N3 -1.1(2) . . . . ? O3 Cu1 N2 N3 108.8(2) . . . . ? N1 Cu1 N2 N3 -168.0(2) . . . . ? C6 N2 N3 C10 -175.8(3) . . . . ? Cu1 N2 N3 C10 1.1(3) . . . . ? N2 Cu1 O1 C10 0.8(2) . . . . ? N7 Cu1 O1 C10 175.4(2) . . . . ? O3 Cu1 O1 C10 -105.1(2) . . . . ? N1 Cu1 O1 C10 31.1(3) . . . . ? Cu1 O1 C10 N3 -0.5(4) . . . . ? Cu1 O1 C10 C11 179.4(2) . . . . ? N2 N3 C10 O1 -0.4(4) . . . . ? N2 N3 C10 C11 179.7(3) . . . . ? C1 N1 C5 C4 1.5(4) . . . . ? Cu1 N1 C5 C4 -158.0(3) . . . . ? C1 N1 C5 C6 -179.0(3) . . . . ? Cu1 N1 C5 C6 21.6(3) . . . . ? C5 N1 C1 C2 -4.0(4) . . . . ? Cu1 N1 C1 C2 150.0(3) . . . . ? C5 N1 C1 C8 169.5(3) . . . . ? Cu1 N1 C1 C8 -36.4(4) . . . . ? N3 N2 C6 C5 177.1(3) . . . . ? Cu1 N2 C6 C5 0.3(4) . . . . ? N3 N2 C6 C7 -2.8(5) . . . . ? Cu1 N2 C6 C7 -179.6(3) . . . . ? N1 C5 C6 N2 -16.2(4) . . . . ? C4 C5 C6 N2 163.3(3) . . . . ? N1 C5 C6 C7 163.7(3) . . . . ? C4 C5 C6 C7 -16.8(5) . . . . ? O1 C10 C11 C12 13.9(5) . . . . ? N3 C10 C11 C12 -166.2(3) . . . . ? O1 C10 C11 C16 -166.2(3) . . . . ? N3 C10 C11 C16 13.7(5) . . . . ? C2 C3 C4 C5 -1.8(5) . . . . ? N1 C5 C4 C3 1.4(5) . . . . ? C6 C5 C4 C3 -178.1(3) . . . . ? C4 C3 C2 C1 -0.7(5) . . . . ? N1 C1 C2 C3 3.7(5) . . . . ? C8 C1 C2 C3 -169.8(3) . . . . ? N1 C1 C8 N4 -39.5(4) . . . . ? C2 C1 C8 N4 134.2(3) . . . . ? N1 C1 C8 C9 146.0(3) . . . . ? C2 C1 C8 C9 -40.3(4) . . . . ? N6 C28 C29 N7 -40.2(4) . . . . ? C27 C28 C29 N7 134.3(3) . . . . ? N6 C28 C29 C30 145.6(3) . . . . ? C27 C28 C29 C30 -39.9(5) . . . . ? C28 C29 N7 N8 -176.2(3) . . . . ? C30 C29 N7 N8 -2.1(4) . . . . ? C28 C29 N7 Cu1 -1.2(4) . . . . ? C30 C29 N7 Cu1 172.8(2) . . . . ? N2 Cu1 N7 C29 5.5(11) . . . . ? O1 Cu1 N7 C29 -51.3(3) . . . . ? O3 Cu1 N7 C29 -162.5(3) . . . . ? N1 Cu1 N7 C29 113.4(3) . . . . ? N2 Cu1 N7 N8 -18E1(4) . . . . ? O1 Cu1 N7 N8 123.7(2) . . . . ? O3 Cu1 N7 N8 12.55(19) . . . . ? N1 Cu1 N7 N8 -71.6(2) . . . . ? C1 C8 N4 N5 -176.8(3) . . . . ? C9 C8 N4 N5 -2.4(4) . . . . ? C1 C8 N4 Cu2 -1.1(4) . . . . ? C9 C8 N4 Cu2 173.3(2) . . . . ? N9 Cu2 N4 C8 -2.8(12) . . . . ? O4 Cu2 N4 C8 -53.5(3) . . . . ? O2 Cu2 N4 C8 -165.2(3) . . . . ? N6 Cu2 N4 C8 112.1(3) . . . . ? N9 Cu2 N4 N5 172.8(9) . . . . ? O4 Cu2 N4 N5 122.2(2) . . . . ? O2 Cu2 N4 N5 10.5(2) . . . . ? N6 Cu2 N4 N5 -72.3(2) . . . . ? C29 N7 N8 C33 164.3(3) . . . . ? Cu1 N7 N8 C33 -11.2(3) . . . . ? C8 N4 N5 C17 166.8(3) . . . . ? Cu2 N4 N5 C17 -9.3(3) . . . . ? N7 N8 C33 O3 -0.4(4) . . . . ? N7 N8 C33 C34 -178.8(2) . . . . ? N8 C33 O3 Cu1 10.1(4) . . . . ? C34 C33 O3 Cu1 -171.5(2) . . . . ? N2 Cu1 O3 C33 169.9(2) . . . . ? N7 Cu1 O3 C33 -11.44(19) . . . . ? O1 Cu1 O3 C33 -104.6(2) . . . . ? N1 Cu1 O3 C33 93.2(2) . . . . ? N9 Cu2 O2 C17 172.4(2) . . . . ? N4 Cu2 O2 C17 -9.6(2) . . . . ? O4 Cu2 O2 C17 -101.5(2) . . . . ? N6 Cu2 O2 C17 96.0(2) . . . . ? C45 C46 C41 C42 2.1(5) . . . . ? C45 C46 C41 C40 -175.6(3) . . . . ? O4 C40 C41 C46 15.0(5) . . . . ? N10 C40 C41 C46 -166.8(3) . . . . ? O4 C40 C41 C42 -162.7(3) . . . . ? N10 C40 C41 C42 15.6(5) . . . . ? C46 C41 C42 C43 -2.1(5) . . . . ? C40 C41 C42 C43 175.5(3) . . . . ? O3 C33 C34 C35 -21.6(4) . . . . ? N8 C33 C34 C35 156.9(3) . . . . ? O3 C33 C34 C39 158.7(3) . . . . ? N8 C33 C34 C39 -22.8(4) . . . . ? C39 C34 C35 C36 -1.4(5) . . . . ? C33 C34 C35 C36 178.9(3) . . . . ? C41 C42 C43 C44 1.1(6) . . . . ? C35 C34 C39 C38 2.0(5) . . . . ? C33 C34 C39 C38 -178.3(3) . . . . ? C34 C39 C38 C37 -2.2(6) . . . . ? C39 C38 C37 C36 1.9(6) . . . . ? C20 C19 C18 C23 0.9(5) . . . . ? C20 C19 C18 C17 -178.7(3) . . . . ? C22 C23 C18 C19 -0.3(5) . . . . ? C22 C23 C18 C17 179.3(3) . . . . ? C12 C11 C16 C15 -0.9(5) . . . . ? C10 C11 C16 C15 179.1(3) . . . . ? C16 C11 C12 C13 0.0(6) . . . . ? C10 C11 C12 C13 179.9(3) . . . . ? C13 C14 C15 C16 1.3(7) . . . . ? C11 C16 C15 C14 0.3(6) . . . . ? C15 C14 C13 C12 -2.2(7) . . . . ? C11 C12 C13 C14 1.6(6) . . . . ? C38 C37 C36 C35 -1.3(6) . . . . ? C34 C35 C36 C37 1.1(6) . . . . ? C18 C19 C20 C21 -0.1(6) . . . . ? C18 C23 C22 C21 -1.1(6) . . . . ? C19 C20 C21 C22 -1.3(6) . . . . ? C23 C22 C21 C20 1.9(6) . . . . ? C42 C43 C44 C45 -0.1(7) . . . . ? C43 C44 C45 C46 0.1(7) . . . . ? C41 C46 C45 C44 -1.1(6) . . . . ? C48 N11 C47 O5 172.8(5) . . . . ? C49 N11 C47 O5 0.2(8) . . . . ? Cu2 O2 C17 N5 8.6(4) . . . . ? Cu2 O2 C17 C18 -171.9(2) . . . . ? N4 N5 C17 O2 -0.5(5) . . . . ? N4 N5 C17 C18 180.0(2) . . . . ? C19 C18 C17 O2 160.9(3) . . . . ? C23 C18 C17 O2 -18.7(5) . . . . ? C19 C18 C17 N5 -19.6(5) . . . . ? C23 C18 C17 N5 160.8(3) . . . . ? O6 C50 N12 C52 -2.5(11) . . . . ? O6 C50 N12 C51 -177.1(7) . . . . ? # END of CIF _database_code_depnum_ccdc_archive 'CCDC 907862' ####################################################################### # # 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_ccg_bf24_0m _audit_creation_date 2013-05-19T18:56:28-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ? _chemical_name_common 'C26 H28 Cu N8 O3' _chemical_formula_moiety 'C26 H28 Cu N8 O3' _chemical_formula_sum 'C26 H28 Cu N8 O3' _chemical_formula_weight 564.1 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C12/c1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 20.9870(4) _cell_length_b 18.8090(3) _cell_length_c 15.3539(3) _cell_angle_alpha 90 _cell_angle_beta 113.5360(10) _cell_angle_gamma 90 _cell_volume 5556.66(18) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 139 _cell_measurement_theta_min 3.0306 _cell_measurement_theta_max 24.6395 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.49 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.16 _exptl_crystal_density_diffrn 1.349 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2344 _exptl_special_details ? #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.828 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.79 _exptl_absorpt_correction_T_max 0.88 _exptl_absorpt_process_details 'SADABS V2008/1 (BRUKER AXS)' #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker CCD Smart APEX II' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_av_R_equivalents 0.0352 _diffrn_reflns_av_unetI/netI 0.0257 _diffrn_reflns_number 40220 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.51 _diffrn_reflns_theta_max 25 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.989 _diffrn_measured_fraction_theta_max 0.989 _reflns_number_total 4851 _reflns_number_gt 3827 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'SAINT V7.68A (Bruker AXS, 2009)' _computing_cell_refinement 'APEX2 v2011.2-3 (Bruker AXS, 2009)' _computing_data_reduction 'SAINT/SADABS (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'Pov-Ray for windows Vesion 3.6.2., 2009' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0833P)^2^+17.0239P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 4851 _refine_ls_number_parameters 343 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0788 _refine_ls_R_factor_gt 0.0609 _refine_ls_wR_factor_ref 0.1714 _refine_ls_wR_factor_gt 0.1587 _refine_ls_goodness_of_fit_ref 1.06 _refine_ls_restrained_S_all 1.063 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.718 _refine_diff_density_min -0.561 _refine_diff_density_rms 0.072 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' 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 O1 O 0.57581(15) 0.13138(15) 0.4588(2) 0.0496(7) Uani 1 1 d . . . N5 N 0.48728(19) 0.32480(17) 0.3773(3) 0.0490(8) Uani 1 1 d . . . O2 O 0.42689(16) 0.22883(15) 0.3995(2) 0.0542(8) Uani 1 1 d . . . N4 N 0.52819(17) 0.27332(17) 0.3612(2) 0.0431(8) Uani 1 1 d . . . C8 C 0.4157(2) 0.2926(2) 0.1469(3) 0.0485(10) Uani 1 1 d . . . C17 C 0.4363(2) 0.2954(2) 0.3964(3) 0.0456(9) Uani 1 1 d . . . C9 C 0.3920(3) 0.3684(3) 0.1377(4) 0.0730(15) Uani 1 1 d . . . H9B H 0.4263 0.3983 0.1294 0.11 Uiso 1 1 calc R . . H9C H 0.386 0.3824 0.194 0.11 Uiso 1 1 calc R . . H9A H 0.3487 0.3731 0.0836 0.11 Uiso 1 1 calc R . . C18 C 0.3883(2) 0.3445(2) 0.4165(3) 0.0532(11) Uani 1 1 d . . . C23 C 0.3364(3) 0.3139(3) 0.4390(5) 0.0799(16) Uani 1 1 d . . . H23 H 0.3327 0.2646 0.4386 0.096 Uiso 1 1 calc R . . C19 C 0.3910(3) 0.4194(3) 0.4140(4) 0.0669(13) Uani 1 1 d . . . N7 N 0.4379(3) 0.4549(2) 0.3902(5) 0.111(2) Uani 1 1 d . . . H7D H 0.4375 0.5006 0.3886 0.133 Uiso 1 1 calc R . . H7E H 0.4681 0.4317 0.3767 0.133 Uiso 1 1 calc R . . C20 C 0.3421(3) 0.4580(3) 0.4358(4) 0.0822(17) Uani 1 1 d . . . H20 H 0.3432 0.5074 0.4334 0.099 Uiso 1 1 calc R . . C22 C 0.2900(4) 0.3544(4) 0.4620(5) 0.095(2) Uani 1 1 d . . . H22 H 0.2568 0.3324 0.4786 0.114 Uiso 1 1 calc R . . C21 C 0.2938(4) 0.4273(4) 0.4600(4) 0.0876(18) Uani 1 1 d . . . H21 H 0.263 0.4551 0.4752 0.105 Uiso 1 1 calc R . . Cu1 Cu 0.49609(2) 0.17523(2) 0.35407(3) 0.0438(2) Uani 1 1 d . . . N2 N 0.46977(17) 0.07744(18) 0.3343(2) 0.0416(7) Uani 1 1 d . . . N1 N 0.40742(17) 0.17728(17) 0.2104(2) 0.0436(8) Uani 1 1 d D . . C1 C 0.3735(2) 0.2348(2) 0.1617(3) 0.0492(10) Uani 1 1 d D . . C2 C 0.3010(3) 0.2354(3) 0.1186(3) 0.0670(14) Uani 1 1 d D . . H2 H 0.2774 0.2767 0.0904 0.08 Uiso 1 1 calc R . . C3 C 0.2652(3) 0.1751(3) 0.1181(4) 0.0748(16) Uani 1 1 d D . . H3 H 0.2169 0.1751 0.0886 0.09 Uiso 1 1 calc R . . C4 C 0.2998(2) 0.1143(3) 0.1608(3) 0.0644(13) Uani 1 1 d D . . H4 H 0.2759 0.072 0.157 0.077 Uiso 1 1 calc R . . C5 C 0.3717(2) 0.1175(2) 0.2100(3) 0.0477(10) Uani 1 1 d D . . C10 C 0.5705(2) 0.0631(2) 0.4545(3) 0.0433(9) Uani 1 1 d . . . N3 N 0.51628(18) 0.02867(17) 0.3917(2) 0.0453(8) Uani 1 1 d . . . C6 C 0.4127(2) 0.0573(2) 0.2664(3) 0.0465(10) Uani 1 1 d . . . C11 C 0.6287(2) 0.0220(2) 0.5232(3) 0.0512(11) Uani 1 1 d . . . C12 C 0.6289(2) -0.0522(3) 0.5344(3) 0.0562(11) Uani 1 1 d . . . N6 N 0.5763(2) -0.0948(2) 0.4793(3) 0.0692(11) Uani 1 1 d . . . H6A H 0.5405 -0.0767 0.4347 0.083 Uiso 1 1 calc R . . H6B H 0.5787 -0.14 0.4889 0.083 Uiso 1 1 calc R . . C16 C 0.6874(2) 0.0603(3) 0.5824(4) 0.0660(14) Uani 1 1 d . . . H16 H 0.6884 0.1092 0.5741 0.079 Uiso 1 1 calc R . . C7 C 0.3904(3) -0.0174(2) 0.2446(3) 0.0614(12) Uani 1 1 d . . . H7A H 0.4236 -0.048 0.2905 0.092 Uiso 1 1 calc R . . H7B H 0.3875 -0.0291 0.1823 0.092 Uiso 1 1 calc R . . H7C H 0.3457 -0.0236 0.2468 0.092 Uiso 1 1 calc R . . C13 C 0.6872(3) -0.0834(3) 0.6073(4) 0.0711(15) Uani 1 1 d . . . H13 H 0.6875 -0.1323 0.6165 0.085 Uiso 1 1 calc R . . C14 C 0.7424(3) -0.0447(4) 0.6640(4) 0.0851(19) Uani 1 1 d . . . H14 H 0.7798 -0.0672 0.7112 0.102 Uiso 1 1 calc R . . C15 C 0.7436(3) 0.0280(4) 0.6522(4) 0.0851(19) Uani 1 1 d . . . H15 H 0.7816 0.0548 0.6908 0.102 Uiso 1 1 calc R . . C31 C 0.4428(11) 0.7935(5) 0.3403(9) 0.254(9) Uani 1 1 d . . . H31A H 0.4815 0.7869 0.4 0.381 Uiso 1 1 calc R . . H31B H 0.4187 0.8365 0.3422 0.381 Uiso 1 1 calc R . . H31C H 0.4592 0.7967 0.2904 0.381 Uiso 1 1 calc R . . O3 O 0.3836(3) 0.6180(3) 0.3549(4) 0.1248(19) Uani 1 1 d . . . N8 N 0.3938(6) 0.7312(6) 0.3217(7) 0.172(4) Uani 1 1 d . . . C30 C 0.4223(7) 0.6550(10) 0.3695(8) 0.274(12) Uani 1 1 d . . . H30 H 0.4689 0.6456 0.4063 0.329 Uiso 1 1 calc R . . C32 C 0.3405(14) 0.7487(15) 0.2398(16) 0.418(19) Uani 1 1 d . . . H32A H 0.3397 0.7994 0.2314 0.626 Uiso 1 1 calc R . . H32B H 0.2976 0.7335 0.2422 0.626 Uiso 1 1 calc R . . H32C H 0.3464 0.7259 0.1877 0.626 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 O1 0.0548(17) 0.0451(17) 0.0453(16) 0.0014(12) 0.0163(14) -0.0039(13) N5 0.054(2) 0.0404(19) 0.052(2) -0.0054(15) 0.0212(18) -0.0009(15) O2 0.0649(19) 0.0423(16) 0.070(2) -0.0028(14) 0.0429(17) 0.0009(14) N4 0.0467(19) 0.0422(18) 0.0419(19) -0.0006(14) 0.0192(15) -0.0023(15) C8 0.051(2) 0.050(2) 0.043(2) 0.0021(19) 0.018(2) 0.009(2) C17 0.053(2) 0.041(2) 0.043(2) -0.0035(17) 0.0187(19) 0.0018(18) C9 0.072(3) 0.059(3) 0.087(4) 0.010(3) 0.031(3) 0.024(3) C18 0.058(3) 0.055(3) 0.045(2) -0.003(2) 0.019(2) 0.010(2) C23 0.085(4) 0.064(3) 0.110(5) -0.003(3) 0.059(4) 0.010(3) C19 0.086(4) 0.054(3) 0.066(3) -0.004(2) 0.035(3) 0.010(3) N7 0.143(5) 0.046(3) 0.185(6) -0.009(3) 0.108(5) 0.003(3) C20 0.109(5) 0.059(3) 0.085(4) -0.002(3) 0.045(4) 0.030(3) C22 0.096(5) 0.094(5) 0.122(6) -0.007(4) 0.074(4) 0.012(4) C21 0.101(5) 0.087(4) 0.090(4) 0.003(3) 0.055(4) 0.033(4) Cu1 0.0444(3) 0.0401(3) 0.0480(3) 0.0015(2) 0.0195(2) 0.0000(2) N2 0.0431(18) 0.0466(19) 0.0396(18) 0.0022(15) 0.0211(15) -0.0025(15) N1 0.0382(17) 0.0477(19) 0.0451(19) -0.0026(15) 0.0168(15) 0.0012(15) C1 0.043(2) 0.064(3) 0.042(2) -0.001(2) 0.0178(19) 0.008(2) C2 0.051(3) 0.091(4) 0.056(3) 0.014(3) 0.018(2) 0.016(3) C3 0.040(3) 0.112(5) 0.063(3) 0.017(3) 0.011(2) -0.003(3) C4 0.050(3) 0.085(4) 0.053(3) 0.006(3) 0.015(2) -0.021(3) C5 0.044(2) 0.061(3) 0.042(2) -0.0057(19) 0.0205(19) -0.0096(19) C10 0.048(2) 0.047(2) 0.045(2) 0.0068(18) 0.028(2) 0.0027(18) N3 0.050(2) 0.0408(18) 0.051(2) 0.0028(16) 0.0264(17) 0.0000(16) C6 0.048(2) 0.053(2) 0.045(2) -0.0026(19) 0.025(2) -0.0083(19) C11 0.050(2) 0.063(3) 0.049(2) 0.017(2) 0.028(2) 0.006(2) C12 0.062(3) 0.056(3) 0.063(3) 0.015(2) 0.038(2) 0.011(2) N6 0.088(3) 0.048(2) 0.074(3) 0.011(2) 0.035(2) 0.008(2) C16 0.048(3) 0.079(3) 0.070(3) 0.026(3) 0.022(2) -0.005(2) C7 0.067(3) 0.059(3) 0.059(3) -0.006(2) 0.027(2) -0.017(2) C13 0.072(4) 0.079(3) 0.076(4) 0.034(3) 0.045(3) 0.027(3) C14 0.057(3) 0.121(5) 0.087(4) 0.050(4) 0.039(3) 0.024(3) C15 0.045(3) 0.126(5) 0.080(4) 0.037(4) 0.020(3) -0.008(3) C31 0.50(3) 0.063(5) 0.205(13) -0.026(7) 0.150(16) -0.086(11) O3 0.102(4) 0.092(3) 0.165(5) 0.018(3) 0.037(4) -0.024(3) N8 0.196(10) 0.176(9) 0.142(8) -0.046(7) 0.066(7) -0.049(7) C30 0.188(12) 0.42(2) 0.118(8) 0.114(11) -0.045(8) -0.208(16) C32 0.39(3) 0.46(4) 0.24(2) 0.16(2) -0.04(2) 0.18(3) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 O1 C10 1.288(5) . ? O1 Cu1 1.979(3) . ? N5 C17 1.337(6) . ? N5 N4 1.380(5) . ? O2 C17 1.271(5) . ? O2 Cu1 2.102(3) . ? N4 C8 1.284(5) 2_655 ? N4 Cu1 1.952(3) . ? C8 N4 1.284(5) 2_655 ? C8 C1 1.477(6) . ? C8 C9 1.498(6) . ? C17 C18 1.488(6) . ? C9 H9B 0.96 . ? C9 H9C 0.96 . ? C9 H9A 0.96 . ? C18 C23 1.391(7) . ? C18 C19 1.411(7) . ? C23 C22 1.387(8) . ? C23 H23 0.93 . ? C19 N7 1.353(7) . ? C19 C20 1.404(7) . ? N7 H7D 0.86 . ? N7 H7E 0.86 . ? C20 C21 1.341(9) . ? C20 H20 0.93 . ? C22 C21 1.375(9) . ? C22 H22 0.93 . ? C21 H21 0.93 . ? Cu1 N2 1.910(3) . ? Cu1 N1 2.247(3) . ? N2 C6 1.292(5) . ? N2 N3 1.372(5) . ? N1 C1 1.346(5) . ? N1 C5 1.349(5) . ? C1 C2 1.397(6) . ? C2 C3 1.358(8) . ? C2 H2 0.93 . ? C3 C4 1.374(7) . ? C3 H3 0.93 . ? C4 C5 1.392(6) . ? C4 H4 0.93 . ? C5 C6 1.477(6) . ? C10 N3 1.330(5) . ? C10 C11 1.475(6) . ? C6 C7 1.475(6) . ? C11 C16 1.402(7) . ? C11 C12 1.407(6) . ? C12 N6 1.353(6) . ? C12 C13 1.414(7) . ? N6 H6A 0.86 . ? N6 H6B 0.86 . ? C16 C15 1.377(7) . ? C16 H16 0.93 . ? C7 H7A 0.96 . ? C7 H7B 0.96 . ? C7 H7C 0.96 . ? C13 C14 1.351(9) . ? C13 H13 0.93 . ? C14 C15 1.383(9) . ? C14 H14 0.93 . ? C15 H15 0.93 . ? C31 N8 1.510(14) . ? C31 H31A 0.96 . ? C31 H31B 0.96 . ? C31 H31C 0.96 . ? O3 C30 1.024(10) . ? N8 C32 1.347(17) . ? N8 C30 1.614(19) . ? C30 H30 0.93 . ? C32 H32A 0.96 . ? C32 H32B 0.96 . ? C32 H32C 0.96 . ? 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 C10 O1 Cu1 110.3(3) . . ? C17 N5 N4 111.0(3) . . ? C17 O2 Cu1 108.8(2) . . ? C8 N4 N5 118.6(3) 2_655 . ? C8 N4 Cu1 124.8(3) 2_655 . ? N5 N4 Cu1 116.6(3) . . ? N4 C8 C1 115.9(4) 2_655 . ? N4 C8 C9 122.8(4) 2_655 . ? C1 C8 C9 121.2(4) . . ? O2 C17 N5 124.5(4) . . ? O2 C17 C18 118.4(4) . . ? N5 C17 C18 117.1(4) . . ? C8 C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C9 H9A 109.5 . . ? H9B C9 H9A 109.5 . . ? H9C C9 H9A 109.5 . . ? C23 C18 C19 117.6(4) . . ? C23 C18 C17 117.2(4) . . ? C19 C18 C17 125.2(4) . . ? C22 C23 C18 122.3(5) . . ? C22 C23 H23 118.9 . . ? C18 C23 H23 118.9 . . ? N7 C19 C20 119.3(5) . . ? N7 C19 C18 122.8(5) . . ? C20 C19 C18 117.9(5) . . ? C19 N7 H7D 120 . . ? C19 N7 H7E 120 . . ? H7D N7 H7E 120 . . ? C21 C20 C19 123.3(5) . . ? C21 C20 H20 118.3 . . ? C19 C20 H20 118.3 . . ? C21 C22 C23 119.3(6) . . ? C21 C22 H22 120.3 . . ? C23 C22 H22 120.3 . . ? C20 C21 C22 119.5(5) . . ? C20 C21 H21 120.3 . . ? C22 C21 H21 120.3 . . ? N2 Cu1 N4 172.15(13) . . ? N2 Cu1 O1 79.91(13) . . ? N4 Cu1 O1 100.81(13) . . ? N2 Cu1 O2 108.69(12) . . ? N4 Cu1 O2 78.29(12) . . ? O1 Cu1 O2 113.72(12) . . ? N2 Cu1 N1 77.69(13) . . ? N4 Cu1 N1 99.83(13) . . ? O1 Cu1 N1 154.77(12) . . ? O2 Cu1 N1 84.62(12) . . ? C6 N2 N3 121.0(4) . . ? C6 N2 Cu1 121.8(3) . . ? N3 N2 Cu1 117.1(3) . . ? C1 N1 C5 119.8(4) . . ? C1 N1 Cu1 127.3(3) . . ? C5 N1 Cu1 103.4(3) . . ? N1 C1 C2 120.3(4) . . ? N1 C1 C8 117.4(4) . . ? C2 C1 C8 121.9(4) . . ? C3 C2 C1 119.4(5) . . ? C3 C2 H2 120.3 . . ? C1 C2 H2 120.3 . . ? C2 C3 C4 120.5(5) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C3 C4 C5 118.3(5) . . ? C3 C4 H4 120.9 . . ? C5 C4 H4 120.9 . . ? N1 C5 C4 121.3(4) . . ? N1 C5 C6 116.4(4) . . ? C4 C5 C6 122.4(4) . . ? O1 C10 N3 123.6(4) . . ? O1 C10 C11 117.2(4) . . ? N3 C10 C11 119.2(4) . . ? C10 N3 N2 108.9(3) . . ? N2 C6 C7 124.8(4) . . ? N2 C6 C5 112.5(4) . . ? C7 C6 C5 122.7(4) . . ? C16 C11 C12 118.2(4) . . ? C16 C11 C10 117.2(4) . . ? C12 C11 C10 124.7(4) . . ? N6 C12 C11 123.4(4) . . ? N6 C12 C13 118.8(5) . . ? C11 C12 C13 117.9(5) . . ? C12 N6 H6A 120 . . ? C12 N6 H6B 120 . . ? H6A N6 H6B 120 . . ? C15 C16 C11 122.4(5) . . ? C15 C16 H16 118.8 . . ? C11 C16 H16 118.8 . . ? 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 . . ? C14 C13 C12 122.4(5) . . ? C14 C13 H13 118.8 . . ? C12 C13 H13 118.8 . . ? C13 C14 C15 120.2(5) . . ? C13 C14 H14 119.9 . . ? C15 C14 H14 119.9 . . ? C16 C15 C14 118.9(6) . . ? C16 C15 H15 120.5 . . ? C14 C15 H15 120.5 . . ? N8 C31 H31A 109.5 . . ? N8 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? N8 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C32 N8 C31 103.6(16) . . ? C32 N8 C30 131.4(15) . . ? C31 N8 C30 120.2(11) . . ? O3 C30 N8 112.7(13) . . ? O3 C30 H30 123.7 . . ? N8 C30 H30 123.7 . . ? N8 C32 H32A 109.5 . . ? N8 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? N8 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C17 N5 N4 C8 -171.7(4) . . . 2_655 ? C17 N5 N4 Cu1 7.5(4) . . . . ? Cu1 O2 C17 N5 -6.6(5) . . . . ? Cu1 O2 C17 C18 174.1(3) . . . . ? N4 N5 C17 O2 0.0(6) . . . . ? N4 N5 C17 C18 179.3(3) . . . . ? O2 C17 C18 C23 1.0(6) . . . . ? N5 C17 C18 C23 -178.3(4) . . . . ? O2 C17 C18 C19 -178.6(4) . . . . ? N5 C17 C18 C19 2.0(7) . . . . ? C19 C18 C23 C22 -2.4(9) . . . . ? C17 C18 C23 C22 177.9(6) . . . . ? C23 C18 C19 N7 -178.0(6) . . . . ? C17 C18 C19 N7 1.7(8) . . . . ? C23 C18 C19 C20 1.0(8) . . . . ? C17 C18 C19 C20 -179.3(5) . . . . ? N7 C19 C20 C21 179.9(6) . . . . ? C18 C19 C20 C21 0.9(9) . . . . ? C18 C23 C22 C21 1.9(11) . . . . ? C19 C20 C21 C22 -1.4(10) . . . . ? C23 C22 C21 C20 0.0(11) . . . . ? C8 N4 Cu1 N2 -36.0(12) 2_655 . . . ? N5 N4 Cu1 N2 144.9(9) . . . . ? C8 N4 Cu1 O1 58.5(3) 2_655 . . . ? N5 N4 Cu1 O1 -120.6(3) . . . . ? C8 N4 Cu1 O2 170.8(4) 2_655 . . . ? N5 N4 Cu1 O2 -8.4(3) . . . . ? C8 N4 Cu1 N1 -106.9(3) 2_655 . . . ? N5 N4 Cu1 N1 74.0(3) . . . . ? C10 O1 Cu1 N2 4.3(2) . . . . ? C10 O1 Cu1 N4 -167.8(2) . . . . ? C10 O1 Cu1 O2 110.4(2) . . . . ? C10 O1 Cu1 N1 -23.4(4) . . . . ? C17 O2 Cu1 N2 -168.5(3) . . . . ? C17 O2 Cu1 N4 7.7(3) . . . . ? C17 O2 Cu1 O1 104.5(3) . . . . ? C17 O2 Cu1 N1 -93.5(3) . . . . ? N4 Cu1 N2 C6 -84.3(11) . . . . ? O1 Cu1 N2 C6 179.8(3) . . . . ? O2 Cu1 N2 C6 68.0(3) . . . . ? N1 Cu1 N2 C6 -11.9(3) . . . . ? N4 Cu1 N2 N3 91.7(10) . . . . ? O1 Cu1 N2 N3 -4.2(2) . . . . ? O2 Cu1 N2 N3 -116.0(2) . . . . ? N1 Cu1 N2 N3 164.1(3) . . . . ? N2 Cu1 N1 C1 167.9(3) . . . . ? N4 Cu1 N1 C1 -19.7(3) . . . . ? O1 Cu1 N1 C1 -164.2(3) . . . . ? O2 Cu1 N1 C1 57.4(3) . . . . ? N2 Cu1 N1 C5 22.5(2) . . . . ? N4 Cu1 N1 C5 -165.1(3) . . . . ? O1 Cu1 N1 C5 50.4(4) . . . . ? O2 Cu1 N1 C5 -88.0(3) . . . . ? C5 N1 C1 C2 6.4(6) . . . . ? Cu1 N1 C1 C2 -134.2(4) . . . . ? C5 N1 C1 C8 -166.8(4) . . . . ? Cu1 N1 C1 C8 52.7(5) . . . . ? N4 C8 C1 N1 32.1(5) 2_655 . . . ? C9 C8 C1 N1 -150.5(4) . . . . ? N4 C8 C1 C2 -140.9(4) 2_655 . . . ? C9 C8 C1 C2 36.4(6) . . . . ? N1 C1 C2 C3 -6.5(7) . . . . ? C8 C1 C2 C3 166.4(5) . . . . ? C1 C2 C3 C4 0.9(8) . . . . ? C2 C3 C4 C5 4.4(8) . . . . ? C1 N1 C5 C4 -0.8(6) . . . . ? Cu1 N1 C5 C4 147.9(4) . . . . ? C1 N1 C5 C6 -179.1(4) . . . . ? Cu1 N1 C5 C6 -30.4(4) . . . . ? C3 C4 C5 N1 -4.6(7) . . . . ? C3 C4 C5 C6 173.6(4) . . . . ? Cu1 O1 C10 N3 -4.2(4) . . . . ? Cu1 O1 C10 C11 175.4(3) . . . . ? O1 C10 N3 N2 0.9(5) . . . . ? C11 C10 N3 N2 -178.7(3) . . . . ? C6 N2 N3 C10 179.2(3) . . . . ? Cu1 N2 N3 C10 3.2(4) . . . . ? N3 N2 C6 C7 1.6(6) . . . . ? Cu1 N2 C6 C7 177.4(3) . . . . ? N3 N2 C6 C5 -177.0(3) . . . . ? Cu1 N2 C6 C5 -1.1(5) . . . . ? N1 C5 C6 N2 24.5(5) . . . . ? C4 C5 C6 N2 -153.8(4) . . . . ? N1 C5 C6 C7 -154.2(4) . . . . ? C4 C5 C6 C7 27.6(6) . . . . ? O1 C10 C11 C16 -5.1(5) . . . . ? N3 C10 C11 C16 174.5(4) . . . . ? O1 C10 C11 C12 173.8(4) . . . . ? N3 C10 C11 C12 -6.7(6) . . . . ? C16 C11 C12 N6 -177.6(4) . . . . ? C10 C11 C12 N6 3.5(7) . . . . ? C16 C11 C12 C13 2.4(6) . . . . ? C10 C11 C12 C13 -176.4(4) . . . . ? C12 C11 C16 C15 -2.0(7) . . . . ? C10 C11 C16 C15 176.9(5) . . . . ? N6 C12 C13 C14 178.5(5) . . . . ? C11 C12 C13 C14 -1.5(7) . . . . ? C12 C13 C14 C15 0.0(8) . . . . ? C11 C16 C15 C14 0.6(8) . . . . ? C13 C14 C15 C16 0.4(9) . . . . ? C32 N8 C30 O3 -33(3) . . . . ? C31 N8 C30 O3 176.3(13) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N7 H7D O3 0.86 2.44 3.243(7) 155.4 . N7 H7E N5 0.86 2.05 2.695(6) 131.2 . N6 H6B O2 0.86 2.43 3.150(5) 141.6 5_656 N6 H6A N3 0.86 2.09 2.727(5) 130.7 . # END of CIF _database_code_depnum_ccdc_archive 'CCDC 907863'