# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2008 data_global _journal_coden_Cambridge 440 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'L Barbour' 'Liliana Dobrzanska' 'Dewald Kleinhans' _publ_contact_author_name 'L Barbour' _publ_contact_author_email LJB@SUN.AC.ZA _publ_section_title ; Influence of the metal-to-ligand ratio on the formation of metal organic complexes ; # Attachment '1.CIF' data_I _database_code_depnum_ccdc_archive 'CCDC 681408' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common CCl85d23min _chemical_melting_point ? _chemical_formula_moiety 'C28 H28 Cl4 Cu2 N8' _chemical_formula_sum 'C28 H28 Cl4 Cu2 N8' _chemical_formula_weight 745.46 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.0726(13) _cell_length_b 7.3982(11) _cell_length_c 22.319(3) _cell_angle_alpha 90.00 _cell_angle_beta 98.604(2) _cell_angle_gamma 90.00 _cell_volume 1481.2(4) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.671 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 756 _exptl_absorpt_coefficient_mu 1.832 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5632 _exptl_absorpt_correction_T_max 0.7429 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area-detector' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8203 _diffrn_reflns_av_R_equivalents 0.0408 _diffrn_reflns_av_sigmaI/netI 0.0544 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 28.30 _reflns_number_total 3413 _reflns_number_gt 2835 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour 2001)' _computing_publication_material ? _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^)+(0.0519P)^2^+1.4279P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3413 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0665 _refine_ls_R_factor_gt 0.0532 _refine_ls_wR_factor_ref 0.1151 _refine_ls_wR_factor_gt 0.1098 _refine_ls_goodness_of_fit_ref 1.114 _refine_ls_restrained_S_all 1.114 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.11548(5) 0.92761(6) 0.446910(19) 0.01102(14) Uani 1 1 d . . . Cl1 Cl 0.15174(10) 0.70057(13) 0.37779(4) 0.0158(2) Uani 1 1 d . . . Cl2 Cl -0.12365(9) 0.80975(12) 0.49437(4) 0.01332(19) Uani 1 1 d . . . N1 N 0.0089(3) 0.9433(4) 0.61960(13) 0.0130(6) Uani 1 1 d . . . N3 N 0.0814(3) 0.7477(4) 0.69231(13) 0.0101(6) Uani 1 1 d . . . N14 N 0.4082(3) 0.5954(4) 0.55401(13) 0.0116(6) Uani 1 1 d . . . N16 N 0.2670(3) 0.8095(4) 0.50747(13) 0.0121(6) Uani 1 1 d . . . C2 C -0.0150(4) 0.7809(5) 0.64178(16) 0.0133(7) Uani 1 1 d . . . H2 H -0.0901 0.6993 0.6242 0.016 Uiso 1 1 calc R . . C4 C 0.1751(4) 0.8948(5) 0.70220(16) 0.0124(7) Uani 1 1 d . . . H4 H 0.2563 0.9090 0.7340 0.015 Uiso 1 1 calc R . . C5 C 0.1280(4) 1.0163(5) 0.65722(16) 0.0142(8) Uani 1 1 d . . . H5 H 0.1705 1.1320 0.6527 0.017 Uiso 1 1 calc R . . C6 C 0.0985(4) 0.5781(5) 0.72602(16) 0.0120(7) Uani 1 1 d . . . H6A H 0.0077 0.5037 0.7152 0.014 Uiso 1 1 calc R . . H6B H 0.1101 0.6039 0.7700 0.014 Uiso 1 1 calc R . . C7 C 0.2328(4) 0.4736(5) 0.71210(16) 0.0114(7) Uani 1 1 d . . . C8 C 0.3097(4) 0.3558(5) 0.75439(16) 0.0140(7) Uani 1 1 d . . . H8 H 0.2790 0.3424 0.7930 0.017 Uiso 1 1 calc R . . C9 C 0.4312(4) 0.2578(5) 0.74061(17) 0.0152(8) Uani 1 1 d . . . H9 H 0.4831 0.1782 0.7698 0.018 Uiso 1 1 calc R . . C10 C 0.4767(4) 0.2761(5) 0.68395(17) 0.0135(7) Uani 1 1 d . . . H10 H 0.5592 0.2087 0.6744 0.016 Uiso 1 1 calc R . . C11 C 0.4003(4) 0.3940(5) 0.64149(16) 0.0118(7) Uani 1 1 d . . . C12 C 0.2787(4) 0.4884(5) 0.65534(16) 0.0108(7) Uani 1 1 d . . . H12 H 0.2251 0.5651 0.6256 0.013 Uiso 1 1 calc R . . C13 C 0.4503(4) 0.4172(5) 0.57987(16) 0.0135(7) Uani 1 1 d . . . H13A H 0.5599 0.4030 0.5842 0.016 Uiso 1 1 calc R . . H13B H 0.4042 0.3219 0.5520 0.016 Uiso 1 1 calc R . . C15 C 0.2838(4) 0.6337(5) 0.51524(15) 0.0129(7) Uani 1 1 d . . . H15 H 0.2168 0.5455 0.4960 0.015 Uiso 1 1 calc R . . C17 C 0.3866(4) 0.8886(5) 0.54392(17) 0.0165(8) Uani 1 1 d . . . H17 H 0.4044 1.0148 0.5483 0.020 Uiso 1 1 calc R . . C18 C 0.4745(4) 0.7565(5) 0.57241(18) 0.0189(8) Uani 1 1 d . . . H18 H 0.5644 0.7726 0.5998 0.023 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 0.0121(2) 0.0092(2) 0.0111(2) 0.00108(17) -0.00052(15) 0.00162(17) Cl1 0.0176(4) 0.0153(5) 0.0135(4) -0.0017(3) -0.0010(3) 0.0053(3) Cl2 0.0152(4) 0.0094(4) 0.0148(4) -0.0001(3) 0.0004(3) -0.0007(3) N1 0.0131(15) 0.0133(16) 0.0122(15) -0.0011(12) 0.0008(12) 0.0007(12) N3 0.0089(14) 0.0107(15) 0.0107(14) 0.0000(12) 0.0011(11) 0.0026(11) N14 0.0132(15) 0.0104(16) 0.0114(15) 0.0021(12) 0.0026(11) 0.0003(12) N16 0.0149(15) 0.0100(15) 0.0112(14) 0.0017(12) 0.0010(12) -0.0003(12) C2 0.0136(17) 0.0126(19) 0.0137(18) -0.0005(14) 0.0018(14) -0.0015(14) C4 0.0126(17) 0.0107(19) 0.0134(17) -0.0015(14) 0.0004(14) 0.0021(13) C5 0.0148(18) 0.0106(18) 0.0171(19) 0.0011(15) 0.0022(14) -0.0013(14) C6 0.0128(17) 0.0114(18) 0.0120(16) 0.0040(14) 0.0022(13) 0.0002(14) C7 0.0106(17) 0.0088(18) 0.0143(17) -0.0003(14) 0.0002(13) -0.0016(13) C8 0.0154(18) 0.0150(19) 0.0109(17) 0.0000(15) -0.0002(14) -0.0022(15) C9 0.0159(18) 0.0128(19) 0.0153(18) 0.0024(15) -0.0032(14) 0.0016(14) C10 0.0101(17) 0.0086(18) 0.0211(19) 0.0007(15) 0.0003(14) 0.0000(13) C11 0.0156(18) 0.0062(18) 0.0134(17) 0.0002(13) 0.0020(14) -0.0031(13) C12 0.0105(17) 0.0069(17) 0.0140(17) 0.0011(14) -0.0017(13) -0.0017(13) C13 0.0155(18) 0.0111(18) 0.0136(18) 0.0000(14) 0.0015(14) 0.0036(14) C15 0.0134(17) 0.0150(19) 0.0096(16) 0.0011(14) -0.0001(13) 0.0018(14) C17 0.0195(19) 0.0104(19) 0.0183(19) -0.0001(15) -0.0020(15) -0.0010(14) C18 0.0183(19) 0.016(2) 0.021(2) 0.0029(16) -0.0035(15) -0.0017(15) _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 1.971(3) 3_576 ? Cu1 N16 1.981(3) . ? Cu1 Cl1 2.3369(10) . ? Cu1 Cl2 2.3387(10) 3_576 ? Cu1 Cl2 2.6975(10) . ? Cl2 Cu1 2.3387(10) 3_576 ? N1 C2 1.330(5) . ? N1 C5 1.376(5) . ? N1 Cu1 1.971(3) 3_576 ? N3 C2 1.342(4) . ? N3 C4 1.378(5) . ? N3 C6 1.460(4) . ? N14 C15 1.345(4) . ? N14 C18 1.370(5) . ? N14 C13 1.467(5) . ? N16 C15 1.318(5) . ? N16 C17 1.385(5) . ? C2 H2 0.9500 . ? C4 C5 1.368(5) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C7 1.514(5) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.393(5) . ? C7 C12 1.396(5) . ? C8 C9 1.391(5) . ? C8 H8 0.9500 . ? C9 C10 1.395(5) . ? C9 H9 0.9500 . ? C10 C11 1.394(5) . ? C10 H10 0.9500 . ? C11 C12 1.379(5) . ? C11 C13 1.521(5) . ? C12 H12 0.9500 . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C15 H15 0.9500 . ? C17 C18 1.358(5) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? 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 N16 171.06(12) 3_576 . ? N1 Cu1 Cl1 88.41(9) 3_576 . ? N16 Cu1 Cl1 88.94(9) . . ? N1 Cu1 Cl2 89.21(9) 3_576 3_576 ? N16 Cu1 Cl2 91.35(9) . 3_576 ? Cl1 Cu1 Cl2 166.24(4) . 3_576 ? N1 Cu1 Cl2 92.81(9) 3_576 . ? N16 Cu1 Cl2 96.11(9) . . ? Cl1 Cu1 Cl2 103.17(3) . . ? Cl2 Cu1 Cl2 90.48(3) 3_576 . ? Cu1 Cl2 Cu1 89.52(3) 3_576 . ? C2 N1 C5 106.5(3) . . ? C2 N1 Cu1 127.7(2) . 3_576 ? C5 N1 Cu1 125.3(3) . 3_576 ? C2 N3 C4 107.4(3) . . ? C2 N3 C6 126.6(3) . . ? C4 N3 C6 125.5(3) . . ? C15 N14 C18 107.3(3) . . ? C15 N14 C13 125.9(3) . . ? C18 N14 C13 125.9(3) . . ? C15 N16 C17 105.9(3) . . ? C15 N16 Cu1 125.4(3) . . ? C17 N16 Cu1 128.1(3) . . ? N1 C2 N3 110.8(3) . . ? N1 C2 H2 124.6 . . ? N3 C2 H2 124.6 . . ? C5 C4 N3 106.5(3) . . ? C5 C4 H4 126.7 . . ? N3 C4 H4 126.7 . . ? C4 C5 N1 108.7(3) . . ? C4 C5 H5 125.7 . . ? N1 C5 H5 125.7 . . ? N3 C6 C7 111.1(3) . . ? N3 C6 H6A 109.4 . . ? C7 C6 H6A 109.4 . . ? N3 C6 H6B 109.4 . . ? C7 C6 H6B 109.4 . . ? H6A C6 H6B 108.0 . . ? C8 C7 C12 118.5(3) . . ? C8 C7 C6 121.1(3) . . ? C12 C7 C6 120.3(3) . . ? C9 C8 C7 120.6(3) . . ? C9 C8 H8 119.7 . . ? C7 C8 H8 119.7 . . ? C8 C9 C10 120.1(3) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? C11 C10 C9 119.5(3) . . ? C11 C10 H10 120.3 . . ? C9 C10 H10 120.3 . . ? C12 C11 C10 119.9(3) . . ? C12 C11 C13 120.2(3) . . ? C10 C11 C13 120.0(3) . . ? C11 C12 C7 121.4(3) . . ? C11 C12 H12 119.3 . . ? C7 C12 H12 119.3 . . ? N14 C13 C11 111.2(3) . . ? N14 C13 H13A 109.4 . . ? C11 C13 H13A 109.4 . . ? N14 C13 H13B 109.4 . . ? C11 C13 H13B 109.4 . . ? H13A C13 H13B 108.0 . . ? N16 C15 N14 111.2(3) . . ? N16 C15 H15 124.4 . . ? N14 C15 H15 124.4 . . ? C18 C17 N16 108.9(3) . . ? C18 C17 H17 125.5 . . ? N16 C17 H17 125.5 . . ? C17 C18 N14 106.6(3) . . ? C17 C18 H18 126.7 . . ? N14 C18 H18 126.7 . . ? 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 Cl2 Cu1 -89.23(9) 3_576 . . 3_576 ? N16 Cu1 Cl2 Cu1 91.41(9) . . . 3_576 ? Cl1 Cu1 Cl2 Cu1 -178.25(4) . . . 3_576 ? Cl2 Cu1 Cl2 Cu1 0.0 3_576 . . 3_576 ? Cl1 Cu1 N16 C15 -38.6(3) . . . . ? Cl2 Cu1 N16 C15 155.1(3) 3_576 . . . ? Cl2 Cu1 N16 C15 64.5(3) . . . . ? Cl1 Cu1 N16 C17 132.1(3) . . . . ? Cl2 Cu1 N16 C17 -34.1(3) 3_576 . . . ? Cl2 Cu1 N16 C17 -124.7(3) . . . . ? C5 N1 C2 N3 1.1(4) . . . . ? Cu1 N1 C2 N3 -171.3(2) 3_576 . . . ? C4 N3 C2 N1 -1.8(4) . . . . ? C6 N3 C2 N1 -173.9(3) . . . . ? C2 N3 C4 C5 1.7(4) . . . . ? C6 N3 C4 C5 174.0(3) . . . . ? N3 C4 C5 N1 -1.1(4) . . . . ? C2 N1 C5 C4 0.1(4) . . . . ? Cu1 N1 C5 C4 172.6(2) 3_576 . . . ? C2 N3 C6 C7 101.5(4) . . . . ? C4 N3 C6 C7 -69.3(4) . . . . ? N3 C6 C7 C8 152.0(3) . . . . ? N3 C6 C7 C12 -30.5(5) . . . . ? C12 C7 C8 C9 1.1(5) . . . . ? C6 C7 C8 C9 178.7(3) . . . . ? C7 C8 C9 C10 -0.3(6) . . . . ? C8 C9 C10 C11 0.4(6) . . . . ? C9 C10 C11 C12 -1.4(5) . . . . ? C9 C10 C11 C13 179.1(3) . . . . ? C10 C11 C12 C7 2.3(5) . . . . ? C13 C11 C12 C7 -178.2(3) . . . . ? C8 C7 C12 C11 -2.1(5) . . . . ? C6 C7 C12 C11 -179.7(3) . . . . ? C15 N14 C13 C11 -94.4(4) . . . . ? C18 N14 C13 C11 74.0(4) . . . . ? C12 C11 C13 N14 26.9(5) . . . . ? C10 C11 C13 N14 -153.6(3) . . . . ? C17 N16 C15 N14 -0.7(4) . . . . ? Cu1 N16 C15 N14 171.7(2) . . . . ? C18 N14 C15 N16 0.4(4) . . . . ? C13 N14 C15 N16 170.6(3) . . . . ? C15 N16 C17 C18 0.8(4) . . . . ? Cu1 N16 C17 C18 -171.3(3) . . . . ? N16 C17 C18 N14 -0.6(4) . . . . ? C15 N14 C18 C17 0.2(4) . . . . ? C13 N14 C18 C17 -170.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.929 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.784 _refine_diff_density_min -0.674 _refine_diff_density_rms 0.128 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA C6 H6a Cl1 3_566 0.990 2.79 3.633(4) 143 C6 H6b Cl1 4_576 0.990 2.78 3.728(4) 160 C13 H13a Cl1 3_666 0.990 2.74 3.697(4) 164 C13 H13b Cl2 3_566 0.990 2.78 3.589(4) 140 C15 H15 Cl2 3_566 0.950 2.78 3.582(4) 143 # Attachment '2.CIF' data_II _database_code_depnum_ccdc_archive 'CCDC 681409' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common work _chemical_melting_point ? _chemical_formula_moiety 'C28 H28 Cl2 Cu N8, 2(C H4 O)' _chemical_formula_sum 'C30 H36 Cl2 Cu N8 O2' _chemical_formula_weight 675.11 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pnnm _symmetry_space_group_name_Hall '-P 2 2n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, -z+1/2' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, y, -z' '-x-1/2, y-1/2, z-1/2' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 17.992(3) _cell_length_b 7.6710(12) _cell_length_c 11.3090(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1560.8(4) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.436 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 702 _exptl_absorpt_coefficient_mu 0.913 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8106 _exptl_absorpt_correction_T_max 0.9223 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area-detector' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9262 _diffrn_reflns_av_R_equivalents 0.0514 _diffrn_reflns_av_sigmaI/netI 0.0447 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 28.24 _reflns_number_total 1949 _reflns_number_gt 1605 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour 2001)' _computing_publication_material ? _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^)+(0.0475P)^2^+0.2936P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1949 _refine_ls_number_parameters 111 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0610 _refine_ls_R_factor_gt 0.0453 _refine_ls_wR_factor_ref 0.1002 _refine_ls_wR_factor_gt 0.0944 _refine_ls_goodness_of_fit_ref 1.123 _refine_ls_restrained_S_all 1.123 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.0000 0.0000 0.0000 0.01237(16) Uani 1 4 d S . . Cl1 Cl 0.08748(4) 0.30694(9) 0.0000 0.01557(19) Uani 1 2 d S . . O12 O 0.24918(14) 0.4333(3) 0.0000 0.0224(5) Uani 1 2 d S . . N1 N 0.06284(10) -0.1135(2) 0.12720(16) 0.0142(4) Uani 1 1 d . . . N3 N 0.12371(10) -0.3036(2) 0.23650(16) 0.0158(4) Uani 1 1 d . . . C2 C 0.07542(12) -0.2805(3) 0.14724(19) 0.0142(5) Uani 1 1 d . . . H2 H 0.0531 -0.3728 0.1039 0.017 Uiso 1 1 calc R . . C7 C 0.12196(13) -0.5334(3) 0.3930(2) 0.0173(5) Uani 1 1 d . . . C4 C 0.14339(14) -0.1410(3) 0.2765(2) 0.0212(5) Uani 1 1 d . . . H4 H 0.1767 -0.1148 0.3392 0.025 Uiso 1 1 calc R . . C5 C 0.10590(13) -0.0256(3) 0.2087(2) 0.0203(5) Uani 1 1 d . . . H5 H 0.1088 0.0976 0.2160 0.024 Uiso 1 1 calc R . . C8 C 0.06308(13) -0.6511(3) 0.3941(2) 0.0226(6) Uani 1 1 d . . . H8 H 0.0424 -0.6902 0.3215 0.027 Uiso 1 1 calc R . . C10 C 0.15158(18) -0.4749(4) 0.5000 0.0162(7) Uani 1 2 d S . . H10 H 0.1920 -0.3951 0.5000 0.019 Uiso 1 2 calc SR . . C9 C 0.0344(2) -0.7118(5) 0.5000 0.0260(8) Uani 1 2 d S . . H9 H -0.0048 -0.7947 0.5000 0.031 Uiso 1 2 calc SR . . C6 C 0.15391(14) -0.4718(3) 0.2772(2) 0.0213(5) Uani 1 1 d . . . H6A H 0.2085 -0.4610 0.2856 0.026 Uiso 1 1 calc R . . H6B H 0.1440 -0.5612 0.2160 0.026 Uiso 1 1 calc R . . C11 C 0.25514(19) 0.6169(5) 0.0000 0.0248(8) Uani 1 2 d S . . H11A H 0.3017 0.6513 0.0383 0.037 Uiso 0.50 1 calc PR . . H11B H 0.2131 0.6672 0.0433 0.037 Uiso 0.50 1 calc PR . . H11C H 0.2547 0.6597 -0.0817 0.037 Uiso 0.50 1 calc PR . . H12 H 0.204(2) 0.408(5) 0.0000 0.031(11) Uiso 1 2 d S . . 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 0.0169(3) 0.0130(3) 0.0072(3) 0.000 0.000 0.0038(2) Cl1 0.0164(4) 0.0129(4) 0.0174(4) 0.000 0.000 -0.0029(3) O12 0.0165(13) 0.0278(13) 0.0230(14) 0.000 0.000 -0.0032(10) N1 0.0175(9) 0.0142(9) 0.0109(9) 0.0002(7) 0.0006(8) 0.0015(7) N3 0.0220(10) 0.0189(10) 0.0065(9) 0.0004(7) -0.0014(8) 0.0055(8) C2 0.0187(11) 0.0165(11) 0.0076(10) -0.0021(9) -0.0010(8) 0.0014(8) C7 0.0249(12) 0.0160(11) 0.0110(11) 0.0000(9) -0.0002(9) 0.0091(9) C4 0.0254(13) 0.0243(13) 0.0139(12) -0.0013(10) -0.0064(10) -0.0019(10) C5 0.0294(13) 0.0147(11) 0.0167(12) -0.0021(9) -0.0053(10) -0.0023(9) C8 0.0237(13) 0.0203(12) 0.0238(14) -0.0062(10) -0.0068(10) 0.0100(9) C10 0.0226(17) 0.0127(16) 0.0132(16) 0.000 0.000 0.0054(12) C9 0.0237(18) 0.0188(17) 0.035(2) 0.000 0.000 0.0023(14) C6 0.0294(13) 0.0237(13) 0.0107(11) 0.0019(9) -0.0001(10) 0.0134(10) C11 0.0214(18) 0.0280(19) 0.0252(19) 0.000 0.000 -0.0043(15) _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 2.0263(18) . ? Cu1 Cl1 2.8322(8) . ? O12 C11 1.413(4) . ? O12 H12 0.84(4) . ? N1 C2 1.320(3) . ? N1 C5 1.380(3) . ? N3 C2 1.344(3) . ? N3 C4 1.373(3) . ? N3 C6 1.474(3) . ? C2 H2 0.9500 . ? C7 C8 1.392(3) . ? C7 C10 1.396(3) . ? C7 C6 1.507(3) . ? C4 C5 1.351(3) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C8 C9 1.385(3) . ? C8 H8 0.9500 . ? C10 C7 1.396(3) 6_556 ? C10 H10 0.9500 . ? C9 C8 1.385(3) 6_556 ? C9 H9 0.9500 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? 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 N1 89.54(10) 5 6 ? N1 Cu1 N1 90.46(10) 5 2 ? N1 Cu1 N1 180.00(11) 6 2 ? N1 Cu1 N1 180.00(14) 5 . ? N1 Cu1 N1 90.46(10) 6 . ? N1 Cu1 N1 89.54(10) 2 . ? N1 Cu1 Cl1 92.70(5) 5 2 ? N1 Cu1 Cl1 87.30(5) 6 2 ? N1 Cu1 Cl1 92.70(5) 2 2 ? N1 Cu1 Cl1 87.30(5) . 2 ? N1 Cu1 Cl1 87.30(5) 5 . ? N1 Cu1 Cl1 92.70(5) 6 . ? N1 Cu1 Cl1 87.30(5) 2 . ? N1 Cu1 Cl1 92.70(5) . . ? Cl1 Cu1 Cl1 180.00(3) 2 . ? C11 O12 H12 108(3) . . ? C2 N1 C5 105.25(18) . . ? C2 N1 Cu1 129.37(15) . . ? C5 N1 Cu1 125.27(15) . . ? C2 N3 C4 107.10(18) . . ? C2 N3 C6 126.06(19) . . ? C4 N3 C6 126.69(19) . . ? N1 C2 N3 111.58(19) . . ? N1 C2 H2 124.2 . . ? N3 C2 H2 124.2 . . ? C8 C7 C10 119.5(2) . . ? C8 C7 C6 120.1(2) . . ? C10 C7 C6 120.5(2) . . ? C5 C4 N3 106.2(2) . . ? C5 C4 H4 126.9 . . ? N3 C4 H4 126.9 . . ? C4 C5 N1 109.8(2) . . ? C4 C5 H5 125.1 . . ? N1 C5 H5 125.1 . . ? C9 C8 C7 120.6(2) . . ? C9 C8 H8 119.7 . . ? C7 C8 H8 119.7 . . ? C7 C10 C7 120.1(3) . 6_556 ? C7 C10 H10 119.9 . . ? C7 C10 H10 119.9 6_556 . ? C8 C9 C8 119.8(3) 6_556 . ? C8 C9 H9 120.1 6_556 . ? C8 C9 H9 120.1 . . ? N3 C6 C7 113.91(18) . . ? N3 C6 H6A 108.8 . . ? C7 C6 H6A 108.8 . . ? N3 C6 H6B 108.8 . . ? C7 C6 H6B 108.8 . . ? H6A C6 H6B 107.7 . . ? O12 C11 H11A 109.5 . . ? O12 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? O12 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 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 N1 Cu1 N1 C2 -59.2(2) 6 . . . ? N1 Cu1 N1 C2 120.8(2) 2 . . . ? Cl1 Cu1 N1 C2 28.07(18) 2 . . . ? Cl1 Cu1 N1 C2 -151.93(18) . . . . ? N1 Cu1 N1 C5 116.65(17) 6 . . . ? N1 Cu1 N1 C5 -63.35(17) 2 . . . ? Cl1 Cu1 N1 C5 -156.07(18) 2 . . . ? Cl1 Cu1 N1 C5 23.93(18) . . . . ? C5 N1 C2 N3 0.1(2) . . . . ? Cu1 N1 C2 N3 176.58(14) . . . . ? C4 N3 C2 N1 0.0(3) . . . . ? C6 N3 C2 N1 -175.7(2) . . . . ? C2 N3 C4 C5 -0.2(3) . . . . ? C6 N3 C4 C5 175.6(2) . . . . ? N3 C4 C5 N1 0.2(3) . . . . ? C2 N1 C5 C4 -0.2(3) . . . . ? Cu1 N1 C5 C4 -176.87(16) . . . . ? C10 C7 C8 C9 -0.7(4) . . . . ? C6 C7 C8 C9 178.5(2) . . . . ? C8 C7 C10 C7 -0.4(4) . . . 6_556 ? C6 C7 C10 C7 -179.60(17) . . . 6_556 ? C7 C8 C9 C8 1.9(5) . . . 6_556 ? C2 N3 C6 C7 -106.5(3) . . . . ? C4 N3 C6 C7 78.6(3) . . . . ? C8 C7 C6 N3 96.3(2) . . . . ? C10 C7 C6 N3 -84.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.643 _refine_diff_density_min -0.424 _refine_diff_density_rms 0.090 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA O12 H12 Cl1 1_555 0.84(4) 2.24(4) 3.067(3) 173(4) C2 H2 Cl1 1_545 0.95 2.79 3.583(2) 141 C4 H4 O12 4_545 0.95 2.29 3.233(3) 175 # Attachment '3.CIF' data_III _database_code_depnum_ccdc_archive 'CCDC 681410' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common work _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H32 Br2 Cu N8 O2' _chemical_formula_weight 735.98 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.683(2) _cell_length_b 8.762(2) _cell_length_c 10.844(2) _cell_angle_alpha 75.252(4) _cell_angle_beta 67.904(4) _cell_angle_gamma 80.906(4) _cell_volume 737.4(3) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1113 _cell_measurement_theta_min 2.410 _cell_measurement_theta_max 21.243 _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.657 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 371 _exptl_absorpt_coefficient_mu 3.491 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5664 _exptl_absorpt_correction_T_max 0.7599 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area-detector' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8492 _diffrn_reflns_av_R_equivalents 0.0632 _diffrn_reflns_av_sigmaI/netI 0.0936 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 28.27 _reflns_number_total 3382 _reflns_number_gt 2466 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour 2001)' _computing_publication_material ? _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^)+(0.0416P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3382 _refine_ls_number_parameters 195 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0853 _refine_ls_R_factor_gt 0.0542 _refine_ls_wR_factor_ref 0.1063 _refine_ls_wR_factor_gt 0.0970 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.5000 0.5000 0.5000 0.01325(19) Uani 1 2 d S . . C14 C 0.0935(6) 0.6859(6) -0.0298(5) 0.0189(11) Uani 1 1 d . . . H14A H 0.0365 0.6111 0.0555 0.023 Uiso 1 1 calc R . . H14B H 0.0120 0.7300 -0.0758 0.023 Uiso 1 1 calc R . . N15 N 0.2323(4) 0.5997(4) -0.1185(4) 0.0134(8) Uani 1 1 d . . . N4 N 0.2154(5) 0.8953(4) 0.3787(4) 0.0141(8) Uani 1 1 d . . . N18 N 0.4118(5) 0.5289(4) -0.3047(4) 0.0152(8) Uani 1 1 d . . . N2 N 0.3898(5) 0.7118(4) 0.4432(3) 0.0135(8) Uani 1 1 d . . . C19 C 0.2718(6) 0.6136(5) -0.2517(5) 0.0162(10) Uani 1 1 d . . . H19 H 0.2076 0.6766 -0.3028 0.019 Uiso 1 1 calc R . . C7 C 0.0840(6) 0.9664(5) 0.3211(5) 0.0166(10) Uani 1 1 d . . . H7A H 0.0574 1.0783 0.3293 0.020 Uiso 1 1 calc R . . H7B H -0.0185 0.9092 0.3728 0.020 Uiso 1 1 calc R . . C10 C 0.1501(6) 0.8184(5) 0.0046(5) 0.0156(10) Uani 1 1 d . . . C6 C 0.4408(6) 0.8572(5) 0.4306(5) 0.0169(10) Uani 1 1 d . . . H6 H 0.5353 0.8749 0.4478 0.020 Uiso 1 1 calc R . . C13 C 0.2524(6) 1.0611(5) 0.0729(5) 0.0201(11) Uani 1 1 d . . . H13 H 0.2885 1.1436 0.0957 0.024 Uiso 1 1 calc R . . C16 C 0.3532(6) 0.5001(6) -0.0807(5) 0.0210(11) Uani 1 1 d . . . H16 H 0.3591 0.4680 0.0080 0.025 Uiso 1 1 calc R . . C11 C 0.2604(6) 0.9241(6) -0.0949(5) 0.0220(11) Uani 1 1 d . . . H11 H 0.3017 0.9130 -0.1869 0.026 Uiso 1 1 calc R . . C9 C 0.0911(6) 0.8366(5) 0.1384(5) 0.0170(10) Uani 1 1 d . . . H9 H 0.0149 0.7656 0.2070 0.020 Uiso 1 1 calc R . . C3 C 0.2531(6) 0.7395(5) 0.4119(4) 0.0160(10) Uani 1 1 d . . . H3 H 0.1902 0.6596 0.4128 0.019 Uiso 1 1 calc R . . C17 C 0.4617(6) 0.4571(6) -0.1952(5) 0.0197(11) Uani 1 1 d . . . H17 H 0.5585 0.3876 -0.2000 0.024 Uiso 1 1 calc R . . C5 C 0.3338(6) 0.9728(5) 0.3894(5) 0.0198(11) Uani 1 1 d . . . H5 H 0.3402 1.0840 0.3717 0.024 Uiso 1 1 calc R . . C12 C 0.3103(6) 1.0445(6) -0.0616(5) 0.0228(11) Uani 1 1 d . . . H12 H 0.3847 1.1166 -0.1307 0.027 Uiso 1 1 calc R . . C8 C 0.1420(6) 0.9573(5) 0.1739(5) 0.0172(10) Uani 1 1 d . . . Br21 Br 0.88814(6) 0.60248(6) 0.69817(5) 0.01772(15) Uani 1 1 d . . . O20 O 0.7627(4) 0.6272(4) 0.4448(3) 0.0199(7) Uani 1 1 d D . . H20A H 0.799(5) 0.628(6) 0.521(3) 0.038(16) Uiso 1 1 d D . . H20B H 0.853(5) 0.568(8) 0.384(5) 0.10(3) Uiso 1 1 d 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 0.0197(4) 0.0125(4) 0.0088(4) -0.0039(3) -0.0057(3) -0.0002(3) C14 0.018(3) 0.021(3) 0.018(3) -0.005(2) -0.006(2) -0.003(2) N15 0.016(2) 0.017(2) 0.0094(19) -0.0065(16) -0.0046(16) -0.0024(16) N4 0.021(2) 0.013(2) 0.0071(18) -0.0022(15) -0.0042(16) -0.0015(17) N18 0.021(2) 0.014(2) 0.0113(19) -0.0026(16) -0.0074(17) -0.0008(16) N2 0.019(2) 0.016(2) 0.0063(18) -0.0048(15) -0.0024(16) -0.0020(16) C19 0.021(3) 0.018(3) 0.014(2) -0.006(2) -0.008(2) -0.003(2) C7 0.019(2) 0.011(2) 0.018(2) -0.0044(19) -0.005(2) 0.0042(19) C10 0.017(2) 0.016(2) 0.016(2) -0.006(2) -0.007(2) 0.0001(19) C6 0.018(3) 0.017(3) 0.021(3) -0.007(2) -0.009(2) -0.004(2) C13 0.026(3) 0.016(3) 0.021(3) -0.006(2) -0.008(2) -0.005(2) C16 0.029(3) 0.022(3) 0.017(3) -0.010(2) -0.012(2) 0.001(2) C11 0.027(3) 0.026(3) 0.014(2) -0.007(2) -0.006(2) -0.002(2) C9 0.018(3) 0.017(3) 0.012(2) -0.0008(19) -0.003(2) 0.000(2) C3 0.026(3) 0.012(2) 0.010(2) -0.0023(18) -0.006(2) -0.003(2) C17 0.021(3) 0.021(3) 0.018(3) -0.008(2) -0.007(2) 0.001(2) C5 0.030(3) 0.014(3) 0.021(3) -0.006(2) -0.011(2) -0.008(2) C12 0.025(3) 0.022(3) 0.016(3) 0.001(2) -0.003(2) -0.009(2) C8 0.018(2) 0.017(3) 0.018(2) -0.008(2) -0.008(2) 0.006(2) Br21 0.0210(3) 0.0185(3) 0.0155(3) -0.00604(19) -0.0064(2) -0.0029(2) O20 0.0209(19) 0.0192(18) 0.0191(19) -0.0025(15) -0.0084(16) 0.0009(15) _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 2.009(4) . ? Cu1 N2 2.009(4) 2_666 ? Cu1 N18 2.031(4) 2_665 ? Cu1 N18 2.031(4) 1_556 ? C14 N15 1.469(6) . ? C14 C10 1.506(6) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? N15 C19 1.330(5) . ? N15 C16 1.372(6) . ? N4 C3 1.341(6) . ? N4 C5 1.372(6) . ? N4 C7 1.481(6) . ? N18 C19 1.329(6) . ? N18 C17 1.384(6) . ? N18 Cu1 2.031(4) 1_554 ? N2 C3 1.324(6) . ? N2 C6 1.372(6) . ? C19 H19 0.9500 . ? C7 C8 1.502(6) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C10 C9 1.388(6) . ? C10 C11 1.390(6) . ? C6 C5 1.369(6) . ? C6 H6 0.9500 . ? C13 C8 1.386(7) . ? C13 C12 1.391(6) . ? C13 H13 0.9500 . ? C16 C17 1.348(6) . ? C16 H16 0.9500 . ? C11 C12 1.373(7) . ? C11 H11 0.9500 . ? C9 C8 1.394(6) . ? C9 H9 0.9500 . ? C3 H3 0.9500 . ? C17 H17 0.9500 . ? C5 H5 0.9500 . ? C12 H12 0.9500 . ? O20 H20A 0.99(4) . ? O20 H20B 0.99(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Cu1 N2 180.000(1) . 2_666 ? N2 Cu1 N18 90.17(14) . 2_665 ? N2 Cu1 N18 89.83(14) 2_666 2_665 ? N2 Cu1 N18 89.83(14) . 1_556 ? N2 Cu1 N18 90.17(14) 2_666 1_556 ? N18 Cu1 N18 180.0 2_665 1_556 ? N15 C14 C10 112.4(4) . . ? N15 C14 H14A 109.1 . . ? C10 C14 H14A 109.1 . . ? N15 C14 H14B 109.1 . . ? C10 C14 H14B 109.1 . . ? H14A C14 H14B 107.8 . . ? C19 N15 C16 107.5(4) . . ? C19 N15 C14 126.5(4) . . ? C16 N15 C14 125.8(4) . . ? C3 N4 C5 107.7(4) . . ? C3 N4 C7 124.6(4) . . ? C5 N4 C7 127.1(4) . . ? C19 N18 C17 104.3(4) . . ? C19 N18 Cu1 123.8(3) . 1_554 ? C17 N18 Cu1 131.4(3) . 1_554 ? C3 N2 C6 106.2(4) . . ? C3 N2 Cu1 127.2(3) . . ? C6 N2 Cu1 126.6(3) . . ? N18 C19 N15 112.0(4) . . ? N18 C19 H19 124.0 . . ? N15 C19 H19 124.0 . . ? N4 C7 C8 110.1(4) . . ? N4 C7 H7A 109.6 . . ? C8 C7 H7A 109.6 . . ? N4 C7 H7B 109.6 . . ? C8 C7 H7B 109.6 . . ? H7A C7 H7B 108.2 . . ? C9 C10 C11 118.8(4) . . ? C9 C10 C14 119.6(4) . . ? C11 C10 C14 121.5(4) . . ? C5 C6 N2 109.2(4) . . ? C5 C6 H6 125.4 . . ? N2 C6 H6 125.4 . . ? C8 C13 C12 120.1(4) . . ? C8 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C17 C16 N15 106.0(4) . . ? C17 C16 H16 127.0 . . ? N15 C16 H16 127.0 . . ? C12 C11 C10 120.7(4) . . ? C12 C11 H11 119.6 . . ? C10 C11 H11 119.6 . . ? C10 C9 C8 121.1(4) . . ? C10 C9 H9 119.5 . . ? C8 C9 H9 119.5 . . ? N2 C3 N4 111.0(4) . . ? N2 C3 H3 124.5 . . ? N4 C3 H3 124.5 . . ? C16 C17 N18 110.2(4) . . ? C16 C17 H17 124.9 . . ? N18 C17 H17 124.9 . . ? C6 C5 N4 105.9(4) . . ? C6 C5 H5 127.1 . . ? N4 C5 H5 127.1 . . ? C11 C12 C13 120.2(4) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? C13 C8 C9 119.0(4) . . ? C13 C8 C7 121.5(4) . . ? C9 C8 C7 119.4(4) . . ? H20A O20 H20B 106(4) . . ? 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 C10 C14 N15 C19 -103.1(5) . . . . ? C10 C14 N15 C16 71.0(6) . . . . ? N18 Cu1 N2 C3 74.6(4) 2_665 . . . ? N18 Cu1 N2 C3 -105.4(4) 1_556 . . . ? N18 Cu1 N2 C6 -106.2(4) 2_665 . . . ? N18 Cu1 N2 C6 73.8(4) 1_556 . . . ? C17 N18 C19 N15 0.2(5) . . . . ? Cu1 N18 C19 N15 173.1(3) 1_554 . . . ? C16 N15 C19 N18 0.0(5) . . . . ? C14 N15 C19 N18 175.0(4) . . . . ? C3 N4 C7 C8 -75.2(5) . . . . ? C5 N4 C7 C8 94.7(5) . . . . ? N15 C14 C10 C9 -133.7(4) . . . . ? N15 C14 C10 C11 46.5(6) . . . . ? C3 N2 C6 C5 -0.8(5) . . . . ? Cu1 N2 C6 C5 179.8(3) . . . . ? C19 N15 C16 C17 -0.3(5) . . . . ? C14 N15 C16 C17 -175.3(4) . . . . ? C9 C10 C11 C12 0.0(7) . . . . ? C14 C10 C11 C12 179.9(4) . . . . ? C11 C10 C9 C8 -0.6(7) . . . . ? C14 C10 C9 C8 179.5(4) . . . . ? C6 N2 C3 N4 0.6(5) . . . . ? Cu1 N2 C3 N4 179.9(3) . . . . ? C5 N4 C3 N2 -0.1(5) . . . . ? C7 N4 C3 N2 171.4(4) . . . . ? N15 C16 C17 N18 0.4(5) . . . . ? C19 N18 C17 C16 -0.4(5) . . . . ? Cu1 N18 C17 C16 -172.5(3) 1_554 . . . ? N2 C6 C5 N4 0.8(5) . . . . ? C3 N4 C5 C6 -0.4(5) . . . . ? C7 N4 C5 C6 -171.7(4) . . . . ? C10 C11 C12 C13 0.7(7) . . . . ? C8 C13 C12 C11 -0.9(8) . . . . ? C12 C13 C8 C9 0.3(7) . . . . ? C12 C13 C8 C7 176.7(4) . . . . ? C10 C9 C8 C13 0.5(7) . . . . ? C10 C9 C8 C7 -176.0(4) . . . . ? N4 C7 C8 C13 -77.5(5) . . . . ? N4 C7 C8 C9 98.9(5) . . . . ? _diffrn_measured_fraction_theta_max 0.922 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.835 _refine_diff_density_min -0.661 _refine_diff_density_rms 0.135 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA O20 H20a Br21 1_555 0.99(4) 2.28(4) 3.264(3) 174(4) O20 H20b Br21 2_766 0.99(6) 2.49(6) 3.431(4) 160(4) C7 H7a Br21 2_676 0.99 2.83 3.771(5) 158 # Attachment '4.CIF' data_IV _database_code_depnum_ccdc_archive 'CCDC 681411' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H28 Br4 Cu2 N8' _chemical_formula_weight 923.30 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 9.264(5) _cell_length_b 7.469(4) _cell_length_c 22.621(11) _cell_angle_alpha 90.00 _cell_angle_beta 98.926(9) _cell_angle_gamma 90.00 _cell_volume 1546.3(14) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2514 _cell_measurement_theta_min 2.651 _cell_measurement_theta_max 27.809 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.983 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 900 _exptl_absorpt_coefficient_mu 6.578 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1626 _exptl_absorpt_correction_T_max 0.2507 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area-detector' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9476 _diffrn_reflns_av_R_equivalents 0.0428 _diffrn_reflns_av_sigmaI/netI 0.0580 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 28.46 _reflns_number_total 3639 _reflns_number_gt 3051 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour 2001)' _computing_publication_material ? _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^)+(0.0350P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3639 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0445 _refine_ls_R_factor_gt 0.0344 _refine_ls_wR_factor_ref 0.0818 _refine_ls_wR_factor_gt 0.0777 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.009 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.34077(4) 0.18552(4) 0.624859(14) 0.01497(10) Uani 1 1 d . . . Cu1 Cu 0.38216(4) 0.42904(5) 0.554137(17) 0.01153(11) Uani 1 1 d . . . N1 N 0.4927(3) 0.4523(4) 0.37887(11) 0.0123(6) Uani 1 1 d . . . Br2 Br 0.61854(4) 0.29167(4) 0.505173(14) 0.01332(10) Uani 1 1 d . . . C2 C 0.5135(4) 0.2932(4) 0.35671(15) 0.0133(7) Uani 1 1 d . . . H2 H 0.5871 0.2112 0.3735 0.016 Uiso 1 1 calc R . . N3 N 0.4167(3) 0.2623(4) 0.30720(11) 0.0108(6) Uani 1 1 d . . . C4 C 0.3267(4) 0.4099(4) 0.29865(14) 0.0132(7) Uani 1 1 d . . . H4 H 0.2457 0.4259 0.2678 0.016 Uiso 1 1 calc R . . C5 C 0.3756(4) 0.5269(5) 0.34236(14) 0.0134(7) Uani 1 1 d . . . H5 H 0.3357 0.6422 0.3472 0.016 Uiso 1 1 calc R . . C6 C 0.3965(3) 0.0939(4) 0.27406(14) 0.0120(7) Uani 1 1 d . . . H6A H 0.4853 0.0194 0.2842 0.014 Uiso 1 1 calc R . . H6B H 0.3835 0.1194 0.2306 0.014 Uiso 1 1 calc R . . C7 C 0.2662(3) -0.0088(4) 0.28813(14) 0.0114(7) Uani 1 1 d . . . C8 C 0.1921(4) -0.1261(5) 0.24686(15) 0.0162(7) Uani 1 1 d . . . H8 H 0.2217 -0.1397 0.2087 0.019 Uiso 1 1 calc R . . C9 C 0.0740(4) -0.2245(5) 0.26091(15) 0.0167(7) Uani 1 1 d . . . H9 H 0.0244 -0.3063 0.2326 0.020 Uiso 1 1 calc R . . C10 C 0.0291(4) -0.2029(4) 0.31621(15) 0.0151(7) Uani 1 1 d . . . H10 H -0.0518 -0.2692 0.3256 0.018 Uiso 1 1 calc R . . C11 C 0.1020(4) -0.0848(4) 0.35771(14) 0.0131(7) Uani 1 1 d . . . C12 C 0.2208(3) 0.0092(4) 0.34362(13) 0.0118(7) Uani 1 1 d . . . H12 H 0.2726 0.0877 0.3725 0.014 Uiso 1 1 calc R . . C13 C 0.0526(4) -0.0605(4) 0.41819(14) 0.0139(7) Uani 1 1 d . . . H13A H -0.0550 -0.0723 0.4134 0.017 Uiso 1 1 calc R . . H13B H 0.0959 -0.1562 0.4456 0.017 Uiso 1 1 calc R . . N14 N 0.0954(3) 0.1133(4) 0.44442(11) 0.0112(6) Uani 1 1 d . . . C15 C 0.2150(4) 0.1482(5) 0.48366(14) 0.0124(7) Uani 1 1 d . . . H15 H 0.2803 0.0593 0.5021 0.015 Uiso 1 1 calc R . . N16 N 0.2311(3) 0.3220(4) 0.49365(12) 0.0135(6) Uani 1 1 d . . . C17 C 0.1151(4) 0.4013(5) 0.45763(15) 0.0186(8) Uani 1 1 d . . . H17 H 0.0974 0.5265 0.4545 0.022 Uiso 1 1 calc R . . C18 C 0.0306(4) 0.2739(5) 0.42741(16) 0.0205(8) Uani 1 1 d . . . H18 H -0.0565 0.2920 0.3998 0.025 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 Br1 0.01675(19) 0.01671(18) 0.01059(17) 0.00022(12) -0.00062(13) -0.00526(13) Cu1 0.0126(2) 0.0114(2) 0.0097(2) -0.00142(15) -0.00119(15) -0.00150(16) N1 0.0139(15) 0.0125(14) 0.0102(14) 0.0016(11) 0.0008(11) -0.0005(11) Br2 0.01454(18) 0.01196(17) 0.01278(17) 0.00021(12) -0.00002(13) 0.00125(12) C2 0.0138(17) 0.0133(17) 0.0133(16) 0.0014(13) 0.0032(13) -0.0017(13) N3 0.0116(14) 0.0121(13) 0.0085(13) -0.0007(10) 0.0006(11) -0.0045(11) C4 0.0114(17) 0.0122(16) 0.0149(16) 0.0036(13) -0.0014(13) -0.0007(13) C5 0.0131(17) 0.0141(16) 0.0131(16) 0.0011(13) 0.0025(13) -0.0005(13) C6 0.0130(17) 0.0138(16) 0.0085(15) -0.0031(12) -0.0011(13) 0.0001(13) C7 0.0108(16) 0.0110(16) 0.0117(16) 0.0012(12) -0.0004(13) -0.0009(13) C8 0.0184(18) 0.0203(18) 0.0098(16) -0.0041(13) 0.0014(13) 0.0023(15) C9 0.0155(18) 0.0167(18) 0.0161(18) -0.0061(14) -0.0033(14) -0.0036(14) C10 0.0124(17) 0.0137(17) 0.0185(18) -0.0027(13) 0.0006(14) 0.0003(13) C11 0.0140(17) 0.0119(16) 0.0134(16) 0.0011(13) 0.0017(13) 0.0009(13) C12 0.0144(17) 0.0111(16) 0.0084(15) -0.0031(12) -0.0033(13) -0.0010(13) C13 0.0124(17) 0.0141(17) 0.0143(17) -0.0048(13) -0.0006(13) -0.0050(13) N14 0.0107(14) 0.0129(14) 0.0099(13) -0.0023(11) 0.0018(11) -0.0017(11) C15 0.0131(17) 0.0141(16) 0.0099(15) -0.0001(13) 0.0013(13) -0.0002(13) N16 0.0134(15) 0.0131(14) 0.0136(14) -0.0006(11) 0.0012(11) -0.0014(11) C17 0.0192(19) 0.0140(17) 0.0212(18) 0.0003(14) -0.0017(15) 0.0042(14) C18 0.0151(19) 0.0223(19) 0.0207(19) -0.0026(15) -0.0083(15) 0.0063(15) _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 Br1 Cu1 2.4909(10) . ? Cu1 N16 1.969(3) . ? Cu1 N1 1.970(3) 3_666 ? Cu1 Br2 2.4796(11) 3_666 ? Cu1 Br2 2.7978(11) . ? N1 C2 1.316(4) . ? N1 C5 1.376(4) . ? N1 Cu1 1.970(3) 3_666 ? Br2 Cu1 2.4796(11) 3_666 ? C2 N3 1.342(4) . ? C2 H2 0.9500 . ? N3 C4 1.377(4) . ? N3 C6 1.462(4) . ? C4 C5 1.345(5) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C7 1.505(4) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.383(4) . ? C7 C12 1.391(4) . ? C8 C9 1.395(5) . ? C8 H8 0.9500 . ? C9 C10 1.388(5) . ? C9 H9 0.9500 . ? C10 C11 1.385(4) . ? C10 H10 0.9500 . ? C11 C12 1.384(5) . ? C11 C13 1.519(4) . ? C12 H12 0.9500 . ? C13 N14 1.457(4) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? N14 C15 1.333(4) . ? N14 C18 1.369(4) . ? C15 N16 1.322(4) . ? C15 H15 0.9500 . ? N16 C17 1.377(4) . ? C17 C18 1.349(5) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? 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 N16 Cu1 N1 170.89(11) . 3_666 ? N16 Cu1 Br2 91.36(9) . 3_666 ? N1 Cu1 Br2 89.40(8) 3_666 3_666 ? N16 Cu1 Br1 89.20(9) . . ? N1 Cu1 Br1 88.01(8) 3_666 . ? Br2 Cu1 Br1 166.91(2) 3_666 . ? N16 Cu1 Br2 95.25(9) . . ? N1 Cu1 Br2 93.79(9) 3_666 . ? Br2 Cu1 Br2 91.76(3) 3_666 . ? Br1 Cu1 Br2 101.21(3) . . ? C2 N1 C5 106.6(3) . . ? C2 N1 Cu1 126.6(2) . 3_666 ? C5 N1 Cu1 126.5(2) . 3_666 ? Cu1 Br2 Cu1 88.24(3) 3_666 . ? N1 C2 N3 110.8(3) . . ? N1 C2 H2 124.6 . . ? N3 C2 H2 124.6 . . ? C2 N3 C4 106.9(3) . . ? C2 N3 C6 126.3(3) . . ? C4 N3 C6 126.2(3) . . ? C5 C4 N3 106.9(3) . . ? C5 C4 H4 126.6 . . ? N3 C4 H4 126.6 . . ? C4 C5 N1 108.8(3) . . ? C4 C5 H5 125.6 . . ? N1 C5 H5 125.6 . . ? N3 C6 C7 111.9(3) . . ? N3 C6 H6A 109.2 . . ? C7 C6 H6A 109.2 . . ? N3 C6 H6B 109.2 . . ? C7 C6 H6B 109.2 . . ? H6A C6 H6B 107.9 . . ? C8 C7 C12 118.8(3) . . ? C8 C7 C6 120.7(3) . . ? C12 C7 C6 120.4(3) . . ? C7 C8 C9 120.3(3) . . ? C7 C8 H8 119.8 . . ? C9 C8 H8 119.8 . . ? C10 C9 C8 120.0(3) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C11 C10 C9 120.2(3) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C12 C11 C10 119.2(3) . . ? C12 C11 C13 120.6(3) . . ? C10 C11 C13 120.2(3) . . ? C11 C12 C7 121.5(3) . . ? C11 C12 H12 119.3 . . ? C7 C12 H12 119.3 . . ? N14 C13 C11 111.9(3) . . ? N14 C13 H13A 109.2 . . ? C11 C13 H13A 109.2 . . ? N14 C13 H13B 109.2 . . ? C11 C13 H13B 109.2 . . ? H13A C13 H13B 107.9 . . ? C15 N14 C18 107.4(3) . . ? C15 N14 C13 126.2(3) . . ? C18 N14 C13 125.9(3) . . ? N16 C15 N14 111.4(3) . . ? N16 C15 H15 124.3 . . ? N14 C15 H15 124.3 . . ? C15 N16 C17 105.3(3) . . ? C15 N16 Cu1 124.5(2) . . ? C17 N16 Cu1 129.9(2) . . ? C18 C17 N16 109.6(3) . . ? C18 C17 H17 125.2 . . ? N16 C17 H17 125.2 . . ? C17 C18 N14 106.3(3) . . ? C17 C18 H18 126.9 . . ? N14 C18 H18 126.9 . . ? 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 N16 Cu1 Br2 Cu1 91.53(9) . . . 3_666 ? N1 Cu1 Br2 Cu1 -89.52(8) 3_666 . . 3_666 ? Br2 Cu1 Br2 Cu1 0.0 3_666 . . 3_666 ? Br1 Cu1 Br2 Cu1 -178.24(2) . . . 3_666 ? C5 N1 C2 N3 0.8(4) . . . . ? Cu1 N1 C2 N3 -173.1(2) 3_666 . . . ? N1 C2 N3 C4 -1.7(4) . . . . ? N1 C2 N3 C6 -173.3(3) . . . . ? C2 N3 C4 C5 1.8(4) . . . . ? C6 N3 C4 C5 173.5(3) . . . . ? N3 C4 C5 N1 -1.4(4) . . . . ? C2 N1 C5 C4 0.4(4) . . . . ? Cu1 N1 C5 C4 174.4(2) 3_666 . . . ? C2 N3 C6 C7 101.2(4) . . . . ? C4 N3 C6 C7 -68.8(4) . . . . ? N3 C6 C7 C8 153.2(3) . . . . ? N3 C6 C7 C12 -28.6(4) . . . . ? C12 C7 C8 C9 -0.1(5) . . . . ? C6 C7 C8 C9 178.2(3) . . . . ? C7 C8 C9 C10 1.0(5) . . . . ? C8 C9 C10 C11 -0.5(5) . . . . ? C9 C10 C11 C12 -0.8(5) . . . . ? C9 C10 C11 C13 179.8(3) . . . . ? C10 C11 C12 C7 1.8(5) . . . . ? C13 C11 C12 C7 -178.9(3) . . . . ? C8 C7 C12 C11 -1.3(5) . . . . ? C6 C7 C12 C11 -179.6(3) . . . . ? C12 C11 C13 N14 25.2(4) . . . . ? C10 C11 C13 N14 -155.5(3) . . . . ? C11 C13 N14 C15 -95.2(4) . . . . ? C11 C13 N14 C18 75.6(4) . . . . ? C18 N14 C15 N16 0.6(4) . . . . ? C13 N14 C15 N16 172.8(3) . . . . ? N14 C15 N16 C17 -0.9(4) . . . . ? N14 C15 N16 Cu1 173.8(2) . . . . ? Br2 Cu1 N16 C15 152.3(3) 3_666 . . . ? Br1 Cu1 N16 C15 -40.8(3) . . . . ? Br2 Cu1 N16 C15 60.4(3) . . . . ? Br2 Cu1 N16 C17 -34.3(3) 3_666 . . . ? Br1 Cu1 N16 C17 132.6(3) . . . . ? Br2 Cu1 N16 C17 -126.2(3) . . . . ? C15 N16 C17 C18 0.9(4) . . . . ? Cu1 N16 C17 C18 -173.5(3) . . . . ? N16 C17 C18 N14 -0.5(4) . . . . ? C15 N14 C18 C17 0.0(4) . . . . ? C13 N14 C18 C17 -172.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.934 _diffrn_reflns_theta_full 26.50 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.777 _refine_diff_density_min -0.583 _refine_diff_density_rms 0.139 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA C6 H6a Br1 3_656 0.99 2.85 3.712(4) 146 C6 H6B Br1 4_565 0.99 2.78 3.719(4) 159 C13 H13A Br1 3_556 0.99 2.79 3.742(4) 162 C13 H13B Br2 3_656 0.99 2.89 3.692(4) 139 C15 H15 Br2 3_656 0.95 2.80 3.621(4) 146 # Attachment '5.CIF' data_V _database_code_depnum_ccdc_archive 'CCDC 681412' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common work _chemical_melting_point ? _chemical_formula_moiety 'C28 H28 Cu N10 O6' _chemical_formula_sum 'C28 H28 Cu N10 O6' _chemical_formula_weight 664.14 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.336(5) _cell_length_b 9.369(4) _cell_length_c 13.865(6) _cell_angle_alpha 90.00 _cell_angle_beta 103.089(8) _cell_angle_gamma 90.00 _cell_volume 1434.3(11) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour violet _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.538 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 686 _exptl_absorpt_coefficient_mu 0.824 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8021 _exptl_absorpt_correction_T_max 0.9148 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area-detector' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8758 _diffrn_reflns_av_R_equivalents 0.0501 _diffrn_reflns_av_sigmaI/netI 0.0679 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.65 _diffrn_reflns_theta_max 28.40 _reflns_number_total 3332 _reflns_number_gt 2671 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour 2001)' _computing_publication_material ? _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^)+(0.0451P)^2^+0.8030P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3332 _refine_ls_number_parameters 205 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0704 _refine_ls_R_factor_gt 0.0536 _refine_ls_wR_factor_ref 0.1156 _refine_ls_wR_factor_gt 0.1089 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.5000 0.0000 0.0000 0.01116(14) Uani 1 2 d S . . O21 O 0.47454(19) 0.0721(2) 0.16388(14) 0.0195(5) Uani 1 1 d . . . N19 N 0.3793(2) 0.1355(3) 0.17368(17) 0.0172(5) Uani 1 1 d . . . N1 N 0.4499(2) -0.1980(2) 0.02901(17) 0.0127(5) Uani 1 1 d . . . N14 N -0.1619(2) -0.4142(2) -0.31856(17) 0.0140(5) Uani 1 1 d . . . N16 N -0.3241(2) -0.4651(2) -0.43454(16) 0.0125(5) Uani 1 1 d . . . O22 O 0.3687(2) 0.2667(2) 0.15769(15) 0.0243(5) Uani 1 1 d . . . O20 O 0.2966(2) 0.0675(3) 0.19943(17) 0.0341(6) Uani 1 1 d . . . N3 N 0.3734(2) -0.4135(2) -0.00233(17) 0.0125(5) Uani 1 1 d . . . C7 C 0.1876(2) -0.5489(3) -0.0787(2) 0.0128(6) Uani 1 1 d . . . C12 C 0.1311(3) -0.6581(3) -0.0388(2) 0.0151(6) Uani 1 1 d . . . H12 H 0.1783 -0.7254 0.0048 0.018 Uiso 1 1 calc R . . C15 C -0.2819(2) -0.3986(3) -0.3491(2) 0.0130(6) Uani 1 1 d . . . H15 H -0.3308 -0.3466 -0.3141 0.016 Uiso 1 1 calc R . . C2 C 0.4129(2) -0.2953(3) -0.0401(2) 0.0131(6) Uani 1 1 d . . . H2 H 0.4140 -0.2833 -0.1080 0.016 Uiso 1 1 calc R . . C6 C 0.3244(2) -0.5416(3) -0.0574(2) 0.0146(6) Uani 1 1 d . . . H6A H 0.3584 -0.6270 -0.0188 0.018 Uiso 1 1 calc R . . H6B H 0.3505 -0.5437 -0.1208 0.018 Uiso 1 1 calc R . . C17 C -0.2234(3) -0.5264(3) -0.4590(2) 0.0147(6) Uani 1 1 d . . . H17 H -0.2248 -0.5819 -0.5165 0.018 Uiso 1 1 calc R . . C8 C 0.1169(3) -0.4507(3) -0.1418(2) 0.0137(6) Uani 1 1 d . . . H8 H 0.1551 -0.3761 -0.1698 0.016 Uiso 1 1 calc R . . C9 C -0.0084(3) -0.4599(3) -0.1644(2) 0.0135(6) Uani 1 1 d . . . C5 C 0.4336(3) -0.2571(3) 0.1167(2) 0.0143(6) Uani 1 1 d . . . H5 H 0.4515 -0.2116 0.1796 0.017 Uiso 1 1 calc R . . C10 C -0.0643(3) -0.5719(3) -0.1253(2) 0.0154(6) Uani 1 1 d . . . H10 H -0.1500 -0.5807 -0.1419 0.018 Uiso 1 1 calc R . . C4 C 0.3878(3) -0.3905(3) 0.0981(2) 0.0139(6) Uani 1 1 d . . . H4 H 0.3692 -0.4556 0.1451 0.017 Uiso 1 1 calc R . . C13 C -0.0848(3) -0.3494(3) -0.2296(2) 0.0159(6) Uani 1 1 d . . . H13A H -0.1365 -0.2998 -0.1914 0.019 Uiso 1 1 calc R . . H13B H -0.0311 -0.2775 -0.2498 0.019 Uiso 1 1 calc R . . C11 C 0.0052(3) -0.6695(3) -0.0626(2) 0.0172(6) Uani 1 1 d . . . H11 H -0.0330 -0.7450 -0.0355 0.021 Uiso 1 1 calc R . . C18 C -0.1225(3) -0.4952(3) -0.3884(2) 0.0165(6) Uani 1 1 d . . . H18 H -0.0417 -0.5232 -0.3872 0.020 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 0.0103(2) 0.0095(2) 0.0121(2) 0.00163(19) -0.00087(18) -0.00043(19) O21 0.0234(12) 0.0201(11) 0.0144(10) -0.0003(8) 0.0029(9) 0.0065(9) N19 0.0176(13) 0.0243(14) 0.0093(12) -0.0023(10) 0.0019(10) -0.0006(11) N1 0.0100(12) 0.0134(11) 0.0131(11) 0.0006(9) -0.0009(9) 0.0013(9) N14 0.0143(12) 0.0120(11) 0.0140(12) -0.0008(9) -0.0001(10) -0.0004(9) N16 0.0120(12) 0.0104(11) 0.0129(11) 0.0003(8) -0.0017(10) 0.0006(9) O22 0.0326(13) 0.0182(11) 0.0215(11) 0.0018(9) 0.0048(10) 0.0081(9) O20 0.0316(14) 0.0434(15) 0.0324(14) -0.0047(11) 0.0179(12) -0.0140(12) N3 0.0095(11) 0.0118(11) 0.0151(12) -0.0004(9) 0.0000(10) 0.0009(9) C7 0.0128(14) 0.0113(12) 0.0134(13) -0.0047(10) 0.0013(11) -0.0013(10) C12 0.0172(15) 0.0155(13) 0.0107(13) 0.0002(11) -0.0009(12) 0.0004(11) C15 0.0114(13) 0.0128(13) 0.0141(13) 0.0006(11) 0.0014(11) 0.0009(11) C2 0.0089(13) 0.0137(13) 0.0159(14) 0.0018(11) 0.0008(11) 0.0027(11) C6 0.0128(14) 0.0097(12) 0.0204(15) -0.0031(11) 0.0018(12) 0.0004(11) C17 0.0196(15) 0.0103(13) 0.0133(13) -0.0019(10) 0.0017(12) 0.0002(11) C8 0.0157(14) 0.0123(13) 0.0133(14) -0.0027(10) 0.0035(12) -0.0020(11) C9 0.0136(14) 0.0149(13) 0.0102(13) -0.0046(10) -0.0010(11) 0.0013(11) C5 0.0128(14) 0.0139(13) 0.0148(14) 0.0005(11) 0.0004(11) 0.0026(11) C10 0.0113(14) 0.0193(15) 0.0144(14) -0.0050(11) 0.0004(12) -0.0008(11) C4 0.0136(14) 0.0151(13) 0.0126(13) 0.0022(11) 0.0018(11) 0.0017(11) C13 0.0158(15) 0.0151(14) 0.0138(14) -0.0037(11) -0.0032(12) 0.0009(11) C11 0.0205(16) 0.0152(14) 0.0168(14) -0.0015(11) 0.0060(12) -0.0058(12) C18 0.0147(14) 0.0159(14) 0.0188(14) -0.0021(12) 0.0034(12) 0.0010(12) _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 2.007(2) 3_655 ? Cu1 N1 2.007(2) . ? Cu1 N16 2.021(2) 2_554 ? Cu1 N16 2.021(2) 4_656 ? O21 N19 1.266(3) . ? N19 O22 1.250(3) . ? N19 O20 1.251(3) . ? N1 C2 1.321(3) . ? N1 C5 1.386(3) . ? N14 C15 1.338(4) . ? N14 C18 1.381(4) . ? N14 C13 1.472(3) . ? N16 C15 1.327(3) . ? N16 C17 1.387(4) . ? N16 Cu1 2.021(2) 2_544 ? N3 C2 1.344(3) . ? N3 C4 1.382(3) . ? N3 C6 1.463(3) . ? C7 C12 1.387(4) . ? C7 C8 1.392(4) . ? C7 C6 1.513(4) . ? C12 C11 1.395(4) . ? C12 H12 0.9500 . ? C15 H15 0.9500 . ? C2 H2 0.9500 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C17 C18 1.358(4) . ? C17 H17 0.9500 . ? C8 C9 1.386(4) . ? C8 H8 0.9500 . ? C9 C10 1.397(4) . ? C9 C13 1.512(4) . ? C5 C4 1.355(4) . ? C5 H5 0.9500 . ? C10 C11 1.380(4) . ? C10 H10 0.9500 . ? C4 H4 0.9500 . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C11 H11 0.9500 . ? C18 H18 0.9500 . ? 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 N1 180.00(16) 3_655 . ? N1 Cu1 N16 93.20(9) 3_655 2_554 ? N1 Cu1 N16 86.80(9) . 2_554 ? N1 Cu1 N16 86.80(9) 3_655 4_656 ? N1 Cu1 N16 93.20(9) . 4_656 ? N16 Cu1 N16 180.00(15) 2_554 4_656 ? O22 N19 O20 120.2(3) . . ? O22 N19 O21 119.6(2) . . ? O20 N19 O21 120.2(3) . . ? C2 N1 C5 106.1(2) . . ? C2 N1 Cu1 123.39(19) . . ? C5 N1 Cu1 130.18(18) . . ? C15 N14 C18 107.7(2) . . ? C15 N14 C13 126.1(2) . . ? C18 N14 C13 126.1(2) . . ? C15 N16 C17 105.2(2) . . ? C15 N16 Cu1 126.57(19) . 2_544 ? C17 N16 Cu1 127.32(18) . 2_544 ? C2 N3 C4 106.9(2) . . ? C2 N3 C6 126.4(2) . . ? C4 N3 C6 126.7(2) . . ? C12 C7 C8 119.1(3) . . ? C12 C7 C6 120.0(3) . . ? C8 C7 C6 120.8(2) . . ? C7 C12 C11 120.1(3) . . ? C7 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? N16 C15 N14 111.5(2) . . ? N16 C15 H15 124.2 . . ? N14 C15 H15 124.2 . . ? N1 C2 N3 111.4(2) . . ? N1 C2 H2 124.3 . . ? N3 C2 H2 124.3 . . ? N3 C6 C7 113.0(2) . . ? N3 C6 H6A 109.0 . . ? C7 C6 H6A 109.0 . . ? N3 C6 H6B 109.0 . . ? C7 C6 H6B 109.0 . . ? H6A C6 H6B 107.8 . . ? C18 C17 N16 109.9(2) . . ? C18 C17 H17 125.1 . . ? N16 C17 H17 125.1 . . ? C9 C8 C7 121.1(3) . . ? C9 C8 H8 119.5 . . ? C7 C8 H8 119.5 . . ? C8 C9 C10 119.4(3) . . ? C8 C9 C13 120.8(3) . . ? C10 C9 C13 119.8(3) . . ? C4 C5 N1 108.9(2) . . ? C4 C5 H5 125.6 . . ? N1 C5 H5 125.6 . . ? C11 C10 C9 119.9(3) . . ? C11 C10 H10 120.1 . . ? C9 C10 H10 120.1 . . ? C5 C4 N3 106.7(2) . . ? C5 C4 H4 126.6 . . ? N3 C4 H4 126.6 . . ? N14 C13 C9 111.7(2) . . ? N14 C13 H13A 109.3 . . ? C9 C13 H13A 109.3 . . ? N14 C13 H13B 109.3 . . ? C9 C13 H13B 109.3 . . ? H13A C13 H13B 107.9 . . ? C10 C11 C12 120.4(3) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C17 C18 N14 105.7(3) . . ? C17 C18 H18 127.2 . . ? N14 C18 H18 127.2 . . ? 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 N16 Cu1 N1 C2 68.7(2) 2_554 . . . ? N16 Cu1 N1 C2 -111.3(2) 4_656 . . . ? N16 Cu1 N1 C5 -103.7(2) 2_554 . . . ? N16 Cu1 N1 C5 76.3(2) 4_656 . . . ? C8 C7 C12 C11 0.6(4) . . . . ? C6 C7 C12 C11 -176.6(3) . . . . ? C17 N16 C15 N14 0.0(3) . . . . ? Cu1 N16 C15 N14 169.57(17) 2_544 . . . ? C18 N14 C15 N16 0.4(3) . . . . ? C13 N14 C15 N16 177.0(2) . . . . ? C5 N1 C2 N3 0.1(3) . . . . ? Cu1 N1 C2 N3 -173.86(17) . . . . ? C4 N3 C2 N1 -0.8(3) . . . . ? C6 N3 C2 N1 179.0(2) . . . . ? C2 N3 C6 C7 -101.3(3) . . . . ? C4 N3 C6 C7 78.4(3) . . . . ? C12 C7 C6 N3 -116.6(3) . . . . ? C8 C7 C6 N3 66.3(3) . . . . ? C15 N16 C17 C18 -0.3(3) . . . . ? Cu1 N16 C17 C18 -169.83(19) 2_544 . . . ? C12 C7 C8 C9 0.6(4) . . . . ? C6 C7 C8 C9 177.7(2) . . . . ? C7 C8 C9 C10 -1.8(4) . . . . ? C7 C8 C9 C13 177.5(2) . . . . ? C2 N1 C5 C4 0.6(3) . . . . ? Cu1 N1 C5 C4 174.03(19) . . . . ? C8 C9 C10 C11 1.8(4) . . . . ? C13 C9 C10 C11 -177.4(2) . . . . ? N1 C5 C4 N3 -1.1(3) . . . . ? C2 N3 C4 C5 1.1(3) . . . . ? C6 N3 C4 C5 -178.7(2) . . . . ? C15 N14 C13 C9 126.8(3) . . . . ? C18 N14 C13 C9 -57.1(4) . . . . ? C8 C9 C13 N14 120.9(3) . . . . ? C10 C9 C13 N14 -59.9(3) . . . . ? C9 C10 C11 C12 -0.7(4) . . . . ? C7 C12 C11 C10 -0.5(4) . . . . ? N16 C17 C18 N14 0.5(3) . . . . ? C15 N14 C18 C17 -0.6(3) . . . . ? C13 N14 C18 C17 -177.2(2) . . . . ? _diffrn_measured_fraction_theta_max 0.924 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.619 _refine_diff_density_min -0.364 _refine_diff_density_rms 0.090 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA C6 H6b O20 4_544 0.99 2.44 3.323(4) 149 C15 H15 O22 1_555 0.99 2.42 3.274(4) 149 # Attachment '6.CIF' data_VI _database_code_depnum_ccdc_archive 'CCDC 681413' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common workdew _chemical_melting_point ? _chemical_formula_moiety 'C28 H28 Cu N10 O6' _chemical_formula_sum 'C28 H28 Cu N10 O6' _chemical_formula_weight 664.14 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall '-C 2yc' 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 14.821(6) _cell_length_b 8.908(4) _cell_length_c 21.365(9) _cell_angle_alpha 90.00 _cell_angle_beta 93.632(8) _cell_angle_gamma 90.00 _cell_volume 2815(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour violet _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.567 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1372 _exptl_absorpt_coefficient_mu 0.840 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8635 _exptl_absorpt_correction_T_max 0.8987 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area-detector' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8521 _diffrn_reflns_av_R_equivalents 0.0489 _diffrn_reflns_av_sigmaI/netI 0.0663 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 28.25 _reflns_number_total 3247 _reflns_number_gt 2716 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour 2001)' _computing_publication_material ? _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^)+(0.0532P)^2^+12.8329P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3247 _refine_ls_number_parameters 205 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0962 _refine_ls_R_factor_gt 0.0785 _refine_ls_wR_factor_ref 0.1562 _refine_ls_wR_factor_gt 0.1485 _refine_ls_goodness_of_fit_ref 1.177 _refine_ls_restrained_S_all 1.177 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.0000 0.0000 0.5000 0.01222(19) Uani 1 2 d S . . N1 N 0.1237(2) 0.0609(4) 0.53240(15) 0.0118(7) Uani 1 1 d . . . C2 C 0.2067(3) -0.0057(5) 0.52567(18) 0.0166(8) Uani 1 1 d . . . H2 H 0.2161 -0.0999 0.5062 0.020 Uiso 1 1 calc R . . C3 C 0.2727(3) 0.0854(5) 0.55141(18) 0.0142(8) Uani 1 1 d . . . H3 H 0.3360 0.0675 0.5529 0.017 Uiso 1 1 calc R . . N4 N 0.2305(2) 0.2076(4) 0.57467(15) 0.0119(7) Uani 1 1 d . . . C5 C 0.1415(3) 0.1892(5) 0.56212(18) 0.0140(8) Uani 1 1 d . . . H5 H 0.0968 0.2592 0.5731 0.017 Uiso 1 1 calc R . . C6 C 0.2735(3) 0.3325(5) 0.61002(18) 0.0148(8) Uani 1 1 d . . . H6A H 0.2374 0.4248 0.6020 0.018 Uiso 1 1 calc R . . H6B H 0.3344 0.3501 0.5950 0.018 Uiso 1 1 calc R . . C7 C 0.2817(3) 0.3021(4) 0.67966(18) 0.0136(8) Uani 1 1 d . . . C8 C 0.3594(3) 0.2375(5) 0.70773(19) 0.0154(8) Uani 1 1 d . . . H8 H 0.4074 0.2093 0.6827 0.018 Uiso 1 1 calc R . . C9 C 0.3675(3) 0.2135(5) 0.7723(2) 0.0181(9) Uani 1 1 d . . . H9 H 0.4210 0.1702 0.7913 0.022 Uiso 1 1 calc R . . C10 C 0.2972(3) 0.2533(5) 0.80849(19) 0.0186(9) Uani 1 1 d . . . H10 H 0.3027 0.2371 0.8525 0.022 Uiso 1 1 calc R . . C11 C 0.2186(3) 0.3168(4) 0.78121(19) 0.0143(8) Uani 1 1 d . . . C12 C 0.2116(3) 0.3396(4) 0.71670(18) 0.0144(8) Uani 1 1 d . . . H12 H 0.1578 0.3817 0.6977 0.017 Uiso 1 1 calc R . . C13 C 0.1419(3) 0.3601(5) 0.82052(19) 0.0192(9) Uani 1 1 d . . . H13A H 0.1642 0.4322 0.8532 0.023 Uiso 1 1 calc R . . H13B H 0.0942 0.4106 0.7936 0.023 Uiso 1 1 calc R . . N14 N 0.1028(2) 0.2286(4) 0.85078(15) 0.0155(7) Uani 1 1 d . . . C15 C 0.0877(2) 0.2135(5) 0.91183(18) 0.0128(8) Uani 1 1 d . . . H15 H 0.1051 0.2845 0.9435 0.015 Uiso 1 1 calc R . . N16 N 0.0453(2) 0.0855(4) 0.92157(15) 0.0121(7) Uani 1 1 d . . . C17 C 0.0308(3) 0.0199(4) 0.86355(18) 0.0154(8) Uani 1 1 d . . . H17 H -0.0003 -0.0720 0.8554 0.018 Uiso 1 1 calc R . . C18 C 0.0677(3) 0.1063(5) 0.81974(19) 0.0165(9) Uani 1 1 d . . . H18 H 0.0690 0.0858 0.7762 0.020 Uiso 1 1 calc R . . N19 N -0.0443(2) 0.3794(4) 0.43267(16) 0.0160(7) Uani 1 1 d . . . O20 O 0.0036(2) 0.2673(3) 0.44604(15) 0.0250(7) Uani 1 1 d . . . O21 O -0.1194(2) 0.3947(4) 0.45577(15) 0.0269(7) Uani 1 1 d . . . O22 O -0.0175(2) 0.4761(3) 0.39575(16) 0.0290(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0072(3) 0.0192(4) 0.0105(3) -0.0068(3) 0.0022(2) -0.0022(3) N1 0.0082(15) 0.0193(17) 0.0080(15) -0.0024(13) -0.0001(12) -0.0006(13) C2 0.0171(19) 0.019(2) 0.0137(18) -0.0031(18) 0.0035(15) 0.0055(18) C3 0.0086(18) 0.022(2) 0.0120(19) 0.0037(16) 0.0017(15) 0.0035(15) N4 0.0093(15) 0.0177(17) 0.0088(15) -0.0005(13) 0.0021(12) -0.0028(13) C5 0.0102(18) 0.022(2) 0.0101(18) -0.0009(16) 0.0027(15) 0.0032(16) C6 0.016(2) 0.017(2) 0.0110(19) -0.0017(16) 0.0025(16) -0.0055(16) C7 0.0150(19) 0.0141(19) 0.0115(19) -0.0010(15) 0.0011(16) -0.0081(15) C8 0.0132(19) 0.017(2) 0.016(2) 0.0002(16) 0.0012(16) -0.0049(15) C9 0.015(2) 0.019(2) 0.020(2) 0.0038(17) -0.0070(17) -0.0054(16) C10 0.025(2) 0.019(2) 0.011(2) 0.0052(16) -0.0019(17) -0.0074(18) C11 0.018(2) 0.0109(18) 0.015(2) 0.0004(15) 0.0039(16) -0.0047(16) C12 0.0142(19) 0.0150(19) 0.0139(19) 0.0035(16) 0.0004(16) -0.0030(15) C13 0.031(2) 0.014(2) 0.013(2) 0.0013(16) 0.0091(18) -0.0008(17) N14 0.0194(18) 0.0178(17) 0.0100(16) 0.0016(13) 0.0060(14) 0.0004(14) C15 0.0112(18) 0.019(2) 0.0082(18) 0.0004(15) 0.0032(15) 0.0031(15) N16 0.0067(15) 0.0189(17) 0.0109(16) 0.0038(13) 0.0024(12) 0.0009(13) C17 0.0183(19) 0.012(2) 0.0164(19) -0.0013(16) 0.0029(16) -0.0013(15) C18 0.020(2) 0.018(2) 0.0117(19) -0.0025(16) 0.0011(16) 0.0016(17) N19 0.0149(17) 0.0196(18) 0.0133(17) -0.0036(14) -0.0012(14) -0.0011(14) O20 0.0212(16) 0.0211(16) 0.0330(19) 0.0016(14) 0.0040(14) 0.0059(13) O21 0.0186(16) 0.040(2) 0.0231(17) 0.0020(15) 0.0075(13) 0.0117(14) O22 0.0343(18) 0.0232(17) 0.0300(18) 0.0047(14) 0.0070(15) -0.0052(14) _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 1.994(3) . ? Cu1 N1 1.994(3) 5_556 ? Cu1 N16 1.995(3) 6 ? Cu1 N16 1.995(3) 2_556 ? N1 C5 1.325(5) . ? N1 C2 1.382(5) . ? C2 C3 1.361(6) . ? C2 H2 0.9500 . ? C3 N4 1.365(5) . ? C3 H3 0.9500 . ? N4 C5 1.339(5) . ? N4 C6 1.468(5) . ? C5 H5 0.9500 . ? C6 C7 1.510(5) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C12 1.386(6) . ? C7 C8 1.389(6) . ? C8 C9 1.393(6) . ? C8 H8 0.9500 . ? C9 C10 1.382(6) . ? C9 H9 0.9500 . ? C10 C11 1.389(6) . ? C10 H10 0.9500 . ? C11 C12 1.390(5) . ? C11 C13 1.506(6) . ? C12 H12 0.9500 . ? C13 N14 1.474(5) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? N14 C15 1.344(5) . ? N14 C18 1.361(5) . ? C15 N16 1.324(5) . ? C15 H15 0.9500 . ? N16 C17 1.375(5) . ? N16 Cu1 1.995(3) 2_556 ? C17 C18 1.354(6) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? N19 O20 1.248(4) . ? N19 O22 1.251(4) . ? N19 O21 1.253(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 N1 180.0 . 5_556 ? N1 Cu1 N16 92.57(13) . 6 ? N1 Cu1 N16 87.43(13) 5_556 6 ? N1 Cu1 N16 87.43(13) . 2_556 ? N1 Cu1 N16 92.57(13) 5_556 2_556 ? N16 Cu1 N16 180.00(9) 6 2_556 ? C5 N1 C2 105.6(3) . . ? C5 N1 Cu1 123.5(3) . . ? C2 N1 Cu1 130.7(3) . . ? C3 C2 N1 108.9(4) . . ? C3 C2 H2 125.6 . . ? N1 C2 H2 125.6 . . ? C2 C3 N4 106.8(3) . . ? C2 C3 H3 126.6 . . ? N4 C3 H3 126.6 . . ? C5 N4 C3 107.3(3) . . ? C5 N4 C6 125.9(3) . . ? C3 N4 C6 126.7(3) . . ? N1 C5 N4 111.4(3) . . ? N1 C5 H5 124.3 . . ? N4 C5 H5 124.3 . . ? N4 C6 C7 112.1(3) . . ? N4 C6 H6A 109.2 . . ? C7 C6 H6A 109.2 . . ? N4 C6 H6B 109.2 . . ? C7 C6 H6B 109.2 . . ? H6A C6 H6B 107.9 . . ? C12 C7 C8 119.0(4) . . ? C12 C7 C6 120.2(4) . . ? C8 C7 C6 120.9(4) . . ? C7 C8 C9 120.5(4) . . ? C7 C8 H8 119.7 . . ? C9 C8 H8 119.7 . . ? C10 C9 C8 119.6(4) . . ? C10 C9 H9 120.2 . . ? C8 C9 H9 120.2 . . ? C9 C10 C11 120.7(4) . . ? C9 C10 H10 119.6 . . ? C11 C10 H10 119.6 . . ? C10 C11 C12 118.9(4) . . ? C10 C11 C13 120.9(4) . . ? C12 C11 C13 120.2(4) . . ? C7 C12 C11 121.3(4) . . ? C7 C12 H12 119.4 . . ? C11 C12 H12 119.4 . . ? N14 C13 C11 111.9(3) . . ? N14 C13 H13A 109.2 . . ? C11 C13 H13A 109.2 . . ? N14 C13 H13B 109.2 . . ? C11 C13 H13B 109.2 . . ? H13A C13 H13B 107.9 . . ? C15 N14 C18 108.1(3) . . ? C15 N14 C13 126.8(4) . . ? C18 N14 C13 124.8(3) . . ? N16 C15 N14 110.4(4) . . ? N16 C15 H15 124.8 . . ? N14 C15 H15 124.8 . . ? C15 N16 C17 105.8(3) . . ? C15 N16 Cu1 130.5(3) . 2_556 ? C17 N16 Cu1 123.6(3) . 2_556 ? C18 C17 N16 109.6(3) . . ? C18 C17 H17 125.2 . . ? N16 C17 H17 125.2 . . ? C17 C18 N14 106.1(3) . . ? C17 C18 H18 127.0 . . ? N14 C18 H18 127.0 . . ? O20 N19 O22 119.8(3) . . ? O20 N19 O21 120.3(4) . . ? O22 N19 O21 120.0(3) . . ? 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 N16 Cu1 N1 C5 140.1(3) 6 . . . ? N16 Cu1 N1 C5 -39.9(3) 2_556 . . . ? N16 Cu1 N1 C2 -33.8(4) 6 . . . ? N16 Cu1 N1 C2 146.2(4) 2_556 . . . ? C5 N1 C2 C3 -0.4(4) . . . . ? Cu1 N1 C2 C3 174.4(3) . . . . ? N1 C2 C3 N4 0.7(4) . . . . ? C2 C3 N4 C5 -0.7(4) . . . . ? C2 C3 N4 C6 176.2(3) . . . . ? C2 N1 C5 N4 -0.1(4) . . . . ? Cu1 N1 C5 N4 -175.3(2) . . . . ? C3 N4 C5 N1 0.5(4) . . . . ? C6 N4 C5 N1 -176.4(3) . . . . ? C5 N4 C6 C7 87.9(5) . . . . ? C3 N4 C6 C7 -88.5(5) . . . . ? N4 C6 C7 C12 -87.9(4) . . . . ? N4 C6 C7 C8 92.6(4) . . . . ? C12 C7 C8 C9 -1.3(6) . . . . ? C6 C7 C8 C9 178.2(4) . . . . ? C7 C8 C9 C10 0.6(6) . . . . ? C8 C9 C10 C11 0.0(6) . . . . ? C9 C10 C11 C12 0.1(6) . . . . ? C9 C10 C11 C13 179.9(4) . . . . ? C8 C7 C12 C11 1.4(6) . . . . ? C6 C7 C12 C11 -178.1(4) . . . . ? C10 C11 C12 C7 -0.8(6) . . . . ? C13 C11 C12 C7 179.3(4) . . . . ? C10 C11 C13 N14 -63.5(5) . . . . ? C12 C11 C13 N14 116.4(4) . . . . ? C11 C13 N14 C15 129.2(4) . . . . ? C11 C13 N14 C18 -57.3(5) . . . . ? C18 N14 C15 N16 0.7(4) . . . . ? C13 N14 C15 N16 175.0(4) . . . . ? N14 C15 N16 C17 -1.8(4) . . . . ? N14 C15 N16 Cu1 -177.6(3) . . . 2_556 ? C15 N16 C17 C18 2.3(4) . . . . ? Cu1 N16 C17 C18 178.5(3) 2_556 . . . ? N16 C17 C18 N14 -1.9(4) . . . . ? C15 N14 C18 C17 0.7(4) . . . . ? C13 N14 C18 C17 -173.8(4) . . . . ? _diffrn_measured_fraction_theta_max 0.929 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.799 _refine_diff_density_min -0.724 _refine_diff_density_rms 0.112 # Attachment '7.CIF' data_VII _database_code_depnum_ccdc_archive 'CCDC 681414' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common work _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C58 H70 Cu2 N18 O19' _chemical_formula_weight 1450.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.7647(14) _cell_length_b 10.8794(17) _cell_length_c 16.984(3) _cell_angle_alpha 89.797(3) _cell_angle_beta 89.368(3) _cell_angle_gamma 84.603(3) _cell_volume 1612.2(4) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1276 _cell_measurement_theta_min 2.334 _cell_measurement_theta_max 19.792 _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.494 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 754 _exptl_absorpt_coefficient_mu 0.747 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8411 _exptl_absorpt_correction_T_max 0.9092 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area-detector' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18918 _diffrn_reflns_av_R_equivalents 0.0805 _diffrn_reflns_av_sigmaI/netI 0.1251 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 28.34 _reflns_number_total 7524 _reflns_number_gt 4628 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour 2001)' _computing_publication_material ? _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^)+(0.0877P)^2^+2.4592P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7524 _refine_ls_number_parameters 463 _refine_ls_number_restraints 13 _refine_ls_R_factor_all 0.1396 _refine_ls_R_factor_gt 0.0811 _refine_ls_wR_factor_ref 0.2005 _refine_ls_wR_factor_gt 0.1743 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.447 _refine_ls_shift/su_max 3.518 _refine_ls_shift/su_mean 0.044 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 0.5000 0.5000 0.5000 0.0137(3) Uani 1 2 d S . . Cu2 Cu 0.5000 0.5000 0.0000 0.0176(4) Uani 1 2 d S . . N2 N 0.4242(7) 0.6663(6) 0.4507(4) 0.0155(14) Uani 1 1 d . . . C3 C 0.3138(9) 0.6893(7) 0.3985(5) 0.0164(17) Uani 1 1 d . . . H3 H 0.2509 0.6292 0.3800 0.020 Uiso 1 1 calc R . . N4 N 0.3017(8) 0.8073(6) 0.3751(4) 0.0184(15) Uani 1 1 d . . . C5 C 0.4120(9) 0.8649(7) 0.4139(5) 0.0181(17) Uani 1 1 d . . . H5 H 0.4316 0.9491 0.4092 0.022 Uiso 1 1 calc R . . C6 C 0.4873(10) 0.7778(7) 0.4601(5) 0.0198(17) Uani 1 1 d . . . H6 H 0.5701 0.7909 0.4937 0.024 Uiso 1 1 calc R . . C7 C 0.1900(10) 0.8647(7) 0.3179(5) 0.0206(18) Uani 1 1 d . . . H7A H 0.1358 0.7992 0.2932 0.025 Uiso 1 1 calc R . . H7B H 0.2461 0.9054 0.2758 0.025 Uiso 1 1 calc R . . C8 C 0.0732(9) 0.9588(7) 0.3550(5) 0.0153(16) Uani 1 1 d . . . C9 C -0.0590(10) 0.9228(7) 0.3896(5) 0.0202(18) Uani 1 1 d . . . H9 H -0.0742 0.8376 0.3926 0.024 Uiso 1 1 calc R . . C10 C -0.1697(10) 1.0098(8) 0.4200(5) 0.0238(19) Uani 1 1 d . . . H10 H -0.2596 0.9843 0.4444 0.029 Uiso 1 1 calc R . . C11 C -0.1483(9) 1.1335(8) 0.4146(5) 0.0215(18) Uani 1 1 d . . . H11 H -0.2246 1.1932 0.4350 0.026 Uiso 1 1 calc R . . C12 C -0.0169(9) 1.1722(7) 0.3798(5) 0.0173(17) Uani 1 1 d . . . C13 C 0.0937(9) 1.0831(7) 0.3507(5) 0.0164(16) Uani 1 1 d . . . H13 H 0.1848 1.1083 0.3274 0.020 Uiso 1 1 calc R . . C14 C 0.0040(10) 1.3068(7) 0.3717(5) 0.0227(19) Uani 1 1 d . . . H14A H 0.0478 1.3218 0.3189 0.027 Uiso 1 1 calc R . . H14B H -0.0975 1.3548 0.3753 0.027 Uiso 1 1 calc R . . N15 N 0.1039(7) 1.3517(6) 0.4314(4) 0.0158(14) Uani 1 1 d . . . C16 C 0.2385(9) 1.3977(7) 0.4184(5) 0.0164(16) Uani 1 1 d . . . H16 H 0.2860 1.4026 0.3681 0.020 Uiso 1 1 calc R . . N17 N 0.2966(7) 1.4353(6) 0.4844(4) 0.0148(14) Uani 1 1 d . . . C18 C 0.1925(9) 1.4112(7) 0.5433(5) 0.0168(17) Uani 1 1 d . . . H18 H 0.2035 1.4273 0.5977 0.020 Uiso 1 1 calc R . . C19 C 0.0734(9) 1.3612(7) 0.5108(5) 0.0179(17) Uani 1 1 d . . . H19 H -0.0147 1.3372 0.5376 0.022 Uiso 1 1 calc R . . O20 O 0.5327(8) 0.6288(6) 0.0832(4) 0.0378(17) Uani 1 1 d . . . C21 C 0.6613(9) 0.6458(7) 0.1213(5) 0.0192(17) Uani 1 1 d . . . H21 H 0.7554 0.5957 0.1147 0.023 Uiso 1 1 calc R . . N22 N 0.6407(8) 0.7424(6) 0.1699(4) 0.0226(16) Uani 1 1 d . . . C23 C 0.4908(10) 0.7890(9) 0.1641(6) 0.031(2) Uani 1 1 d . . . H23 H 0.4417 0.8575 0.1920 0.037 Uiso 1 1 calc R . . C24 C 0.4265(10) 0.7184(8) 0.1111(6) 0.030(2) Uani 1 1 d . . . H24 H 0.3224 0.7295 0.0955 0.036 Uiso 1 1 calc R . . C25 C 0.7570(10) 0.7879(8) 0.2212(5) 0.0242(19) Uani 1 1 d . . . H25A H 0.8239 0.7166 0.2414 0.029 Uiso 1 1 calc R . . H25B H 0.7053 0.8306 0.2669 0.029 Uiso 1 1 calc R . . C26 C 0.8550(10) 0.8756(8) 0.1795(5) 0.0237(19) Uani 1 1 d . . . C27 C 0.8370(10) 1.0008(7) 0.1945(5) 0.0212(18) Uani 1 1 d . . . H27 H 0.7597 1.0328 0.2305 0.025 Uiso 1 1 calc R . . C28 C 0.9303(10) 1.0813(8) 0.1577(5) 0.025(2) Uani 1 1 d . . . C29 C 1.0418(11) 1.0339(8) 0.1045(6) 0.031(2) Uani 1 1 d . . . H29 H 1.1068 1.0876 0.0794 0.037 Uiso 1 1 calc R . . C30 C 1.0591(11) 0.9083(9) 0.0880(6) 0.034(2) Uani 1 1 d . . . H30 H 1.1340 0.8763 0.0507 0.041 Uiso 1 1 calc R . . C31 C 0.9666(11) 0.8304(8) 0.1261(5) 0.029(2) Uani 1 1 d . . . H31 H 0.9798 0.7443 0.1154 0.035 Uiso 1 1 calc R . . C32 C 0.9141(11) 1.2166(7) 0.1773(5) 0.0250(19) Uani 1 1 d . . . H32A H 0.8443 1.2306 0.2233 0.030 Uiso 1 1 calc R . . H32B H 1.0155 1.2417 0.1922 0.030 Uiso 1 1 calc R . . N33 N 0.8538(8) 1.2948(6) 0.1111(4) 0.0183(15) Uani 1 1 d . . . C34 C 0.7078(10) 1.3341(7) 0.0992(5) 0.0205(18) Uani 1 1 d . . . H34 H 0.6253 1.3150 0.1324 0.025 Uiso 1 1 calc R . . N35 N 0.6919(8) 1.4031(6) 0.0351(4) 0.0170(14) Uani 1 1 d . . . C36 C 0.8372(9) 1.4072(7) 0.0050(5) 0.0195(17) Uani 1 1 d . . . H36 H 0.8627 1.4498 -0.0415 0.023 Uiso 1 1 calc R . . C37 C 0.9389(9) 1.3411(7) 0.0521(5) 0.0201(17) Uani 1 1 d . . . H37 H 1.0470 1.3294 0.0454 0.024 Uiso 1 1 calc R . . N38 N 0.4908(7) 0.1538(5) 0.2924(4) 0.0127(13) Uani 1 1 d . . . O39 O 0.4666(8) 0.1583(6) 0.3641(4) 0.0411(17) Uani 1 1 d . . . O40 O 0.5574(10) 0.2323(6) 0.2587(4) 0.050(2) Uani 1 1 d . . . O41 O 0.4539(9) 0.0601(6) 0.2545(4) 0.0446(19) Uani 1 1 d D . . N42 N 0.0851(8) 0.5334(7) 0.2385(4) 0.0251(17) Uani 1 1 d . . . O43 O 0.0049(8) 0.5219(6) 0.1812(4) 0.0367(17) Uani 1 1 d . . . O44 O 0.0305(8) 0.5876(6) 0.2998(4) 0.0331(15) Uani 1 1 d . . . O45 O 0.2205(9) 0.4903(12) 0.2380(4) 0.087(4) Uani 1 1 d . . . O46 O 0.5833(7) 0.4298(5) 0.3639(3) 0.0232(13) Uani 1 1 d . . . H46 H 0.5591 0.3600 0.3505 0.028 Uiso 1 1 calc R . . C47 C 0.5963(10) 0.5049(8) 0.2954(5) 0.0259(19) Uani 1 1 d . . . H47A H 0.5852 0.5921 0.3105 0.039 Uiso 1 1 calc R . . H47B H 0.5158 0.4892 0.2581 0.039 Uiso 1 1 calc R . . H47C H 0.6970 0.4848 0.2705 0.039 Uiso 1 1 calc R . . O48 O 0.3444(9) 0.3907(8) 0.0947(5) 0.049(2) Uani 1 1 d D . . H48A H 0.345(12) 0.3000(14) 0.100(6) 0.05(3) Uiso 1 1 d D . . H48B H 0.35(2) 0.422(9) 0.149(2) 0.17(9) Uiso 1 1 d D . . O49 O 0.390(2) 0.1430(19) 0.0999(12) 0.076(5) Uani 0.50 1 d PDU . . H49B H 0.40(2) 0.082(7) 0.150(2) 0.34(18) Uiso 0.50 1 d PD . . H49A H 0.436(13) 0.078(10) 0.054(4) 0.00(3) Uiso 0.50 1 d PD . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0142(7) 0.0088(7) 0.0181(7) 0.0014(5) -0.0027(5) -0.0008(5) Cu2 0.0188(8) 0.0141(7) 0.0192(8) -0.0030(6) -0.0019(6) 0.0017(6) N2 0.013(3) 0.013(3) 0.019(3) 0.002(3) 0.002(3) 0.000(3) C3 0.019(4) 0.012(4) 0.018(4) 0.002(3) 0.002(3) -0.002(3) N4 0.024(4) 0.011(3) 0.019(4) 0.002(3) -0.002(3) 0.004(3) C5 0.018(4) 0.013(4) 0.024(4) -0.004(3) -0.002(3) -0.004(3) C6 0.025(4) 0.013(4) 0.022(4) -0.001(3) 0.000(3) -0.005(3) C7 0.030(5) 0.015(4) 0.015(4) -0.001(3) -0.006(3) 0.009(3) C8 0.018(4) 0.010(4) 0.017(4) 0.000(3) -0.004(3) 0.004(3) C9 0.029(5) 0.011(4) 0.021(4) 0.002(3) -0.008(4) -0.006(3) C10 0.021(4) 0.025(5) 0.026(5) 0.004(4) 0.001(4) -0.009(4) C11 0.016(4) 0.023(4) 0.026(5) -0.001(4) -0.003(3) -0.001(3) C12 0.021(4) 0.014(4) 0.017(4) -0.001(3) -0.008(3) -0.001(3) C13 0.015(4) 0.017(4) 0.018(4) 0.002(3) -0.003(3) -0.004(3) C14 0.025(5) 0.014(4) 0.029(5) 0.003(3) -0.010(4) -0.003(3) N15 0.016(3) 0.010(3) 0.021(4) -0.002(3) -0.004(3) 0.001(3) C16 0.018(4) 0.010(4) 0.021(4) -0.001(3) -0.001(3) 0.000(3) N17 0.012(3) 0.014(3) 0.018(3) 0.003(3) -0.002(3) 0.000(3) C18 0.020(4) 0.010(4) 0.020(4) 0.003(3) 0.002(3) 0.000(3) C19 0.016(4) 0.015(4) 0.023(4) 0.004(3) 0.001(3) -0.001(3) O20 0.035(4) 0.037(4) 0.041(4) -0.005(3) -0.008(3) 0.001(3) C21 0.017(4) 0.016(4) 0.024(4) -0.003(3) 0.000(3) 0.000(3) N22 0.025(4) 0.019(4) 0.024(4) -0.007(3) -0.003(3) -0.001(3) C23 0.026(5) 0.026(5) 0.039(6) -0.010(4) 0.007(4) 0.007(4) C24 0.018(4) 0.031(5) 0.040(6) -0.015(4) -0.006(4) 0.006(4) C25 0.031(5) 0.020(4) 0.021(4) -0.008(3) -0.003(4) 0.001(4) C26 0.024(5) 0.025(5) 0.021(4) -0.001(4) -0.009(4) 0.003(4) C27 0.025(4) 0.020(4) 0.017(4) -0.003(3) -0.007(3) 0.004(3) C28 0.034(5) 0.016(4) 0.022(5) 0.001(3) -0.011(4) 0.008(4) C29 0.037(6) 0.022(5) 0.034(5) 0.005(4) 0.001(4) 0.001(4) C30 0.038(6) 0.030(5) 0.033(5) 0.004(4) 0.005(4) 0.008(4) C31 0.034(5) 0.021(5) 0.031(5) 0.000(4) 0.000(4) 0.010(4) C32 0.036(5) 0.020(4) 0.019(4) 0.000(3) -0.011(4) -0.004(4) N33 0.021(4) 0.013(3) 0.021(4) -0.003(3) -0.005(3) 0.001(3) C34 0.023(4) 0.014(4) 0.025(5) -0.005(3) 0.000(4) -0.005(3) N35 0.022(4) 0.011(3) 0.018(3) -0.002(3) -0.002(3) -0.001(3) C36 0.025(4) 0.013(4) 0.021(4) -0.004(3) 0.002(3) -0.003(3) C37 0.018(4) 0.017(4) 0.025(4) -0.005(3) 0.002(3) -0.003(3) N38 0.010(3) 0.007(3) 0.022(4) -0.008(3) 0.012(3) -0.004(2) O39 0.045(4) 0.035(4) 0.043(4) -0.003(3) -0.001(3) -0.006(3) O40 0.077(6) 0.031(4) 0.044(4) -0.004(3) 0.016(4) -0.021(4) O41 0.058(5) 0.031(4) 0.047(4) -0.011(3) 0.013(4) -0.014(4) N42 0.024(4) 0.027(4) 0.025(4) 0.013(3) -0.007(3) -0.006(3) O43 0.037(4) 0.033(4) 0.039(4) -0.012(3) -0.016(3) 0.004(3) O44 0.042(4) 0.033(4) 0.025(4) 0.005(3) -0.008(3) -0.007(3) O45 0.028(5) 0.207(12) 0.022(4) 0.009(6) 0.002(3) 0.016(6) O46 0.030(3) 0.017(3) 0.022(3) -0.004(2) 0.001(3) -0.004(3) C47 0.029(5) 0.029(5) 0.019(4) 0.004(4) -0.002(4) -0.002(4) O48 0.039(4) 0.057(5) 0.049(5) 0.022(4) 0.007(4) 0.002(4) O49 0.078(6) 0.074(6) 0.076(6) 0.004(3) -0.006(3) -0.015(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N17 1.998(6) 1_545 ? Cu1 N17 1.998(6) 2_676 ? Cu1 N2 2.048(6) 2_666 ? Cu1 N2 2.048(6) . ? Cu2 N35 1.995(6) 1_545 ? Cu2 N35 1.995(6) 2_675 ? Cu2 O20 2.034(7) 2_665 ? Cu2 O20 2.034(7) . ? N2 C3 1.324(10) . ? N2 C6 1.390(10) . ? C3 N4 1.338(10) . ? C3 H3 0.9500 . ? N4 C5 1.376(10) . ? N4 C7 1.481(10) . ? C5 C6 1.356(11) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.511(10) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.382(11) . ? C8 C13 1.382(10) . ? C9 C10 1.387(12) . ? C9 H9 0.9500 . ? C10 C11 1.379(12) . ? C10 H10 0.9500 . ? C11 C12 1.389(11) . ? C11 H11 0.9500 . ? C12 C13 1.392(11) . ? C12 C14 1.499(11) . ? C13 H13 0.9500 . ? C14 N15 1.461(10) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? N15 C16 1.340(10) . ? N15 C19 1.375(10) . ? C16 N17 1.318(10) . ? C16 H16 0.9500 . ? N17 C18 1.387(10) . ? N17 Cu1 1.998(6) 1_565 ? C18 C19 1.345(11) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? O20 C21 1.334(10) . ? O20 C24 1.366(11) . ? C21 N22 1.338(10) . ? C21 H21 0.9500 . ? N22 C23 1.368(11) . ? N22 C25 1.469(11) . ? C23 C24 1.347(13) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? C25 C26 1.511(13) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 C27 1.381(11) . ? C26 C31 1.384(12) . ? C27 C28 1.394(12) . ? C27 H27 0.9500 . ? C28 C29 1.388(13) . ? C28 C32 1.504(11) . ? C29 C30 1.390(13) . ? C29 H29 0.9500 . ? C30 C31 1.381(13) . ? C30 H30 0.9500 . ? C31 H31 0.9500 . ? C32 N33 1.479(10) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? N33 C34 1.328(10) . ? N33 C37 1.365(10) . ? C34 N35 1.321(10) . ? C34 H34 0.9500 . ? N35 C36 1.372(10) . ? N35 Cu2 1.995(6) 1_565 ? C36 C37 1.357(11) . ? C36 H36 0.9500 . ? C37 H37 0.9500 . ? N38 O40 1.217(9) . ? N38 O39 1.234(9) . ? N38 O41 1.277(9) . ? N42 O43 1.221(9) . ? N42 O45 1.234(10) . ? N42 O44 1.264(9) . ? O46 C47 1.429(10) . ? O46 H46 0.8400 . ? C47 H47A 0.9800 . ? C47 H47B 0.9800 . ? C47 H47C 0.9800 . ? O48 H48A 0.99(2) . ? O48 H48B 0.99(6) . ? O49 H49B 1.08(4) . ? O49 H49A 1.11(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N17 Cu1 N17 180.0(4) 1_545 2_676 ? N17 Cu1 N2 88.5(2) 1_545 2_666 ? N17 Cu1 N2 91.5(2) 2_676 2_666 ? N17 Cu1 N2 91.5(2) 1_545 . ? N17 Cu1 N2 88.5(2) 2_676 . ? N2 Cu1 N2 180.0(3) 2_666 . ? N35 Cu2 N35 180.0(4) 1_545 2_675 ? N35 Cu2 O20 90.9(3) 1_545 2_665 ? N35 Cu2 O20 89.1(3) 2_675 2_665 ? N35 Cu2 O20 89.1(3) 1_545 . ? N35 Cu2 O20 90.9(3) 2_675 . ? O20 Cu2 O20 180.0(4) 2_665 . ? C3 N2 C6 105.2(6) . . ? C3 N2 Cu1 127.9(5) . . ? C6 N2 Cu1 126.7(5) . . ? N2 C3 N4 111.8(7) . . ? N2 C3 H3 124.1 . . ? N4 C3 H3 124.1 . . ? C3 N4 C5 107.3(6) . . ? C3 N4 C7 126.2(7) . . ? C5 N4 C7 126.6(7) . . ? C6 C5 N4 106.4(7) . . ? C6 C5 H5 126.8 . . ? N4 C5 H5 126.8 . . ? C5 C6 N2 109.3(7) . . ? C5 C6 H6 125.3 . . ? N2 C6 H6 125.3 . . ? N4 C7 C8 113.1(6) . . ? N4 C7 H7A 109.0 . . ? C8 C7 H7A 109.0 . . ? N4 C7 H7B 109.0 . . ? C8 C7 H7B 109.0 . . ? H7A C7 H7B 107.8 . . ? C9 C8 C13 119.1(7) . . ? C9 C8 C7 120.7(7) . . ? C13 C8 C7 120.1(7) . . ? C8 C9 C10 120.7(7) . . ? C8 C9 H9 119.7 . . ? C10 C9 H9 119.7 . . ? C11 C10 C9 119.5(8) . . ? C11 C10 H10 120.2 . . ? C9 C10 H10 120.2 . . ? C10 C11 C12 120.9(8) . . ? C10 C11 H11 119.5 . . ? C12 C11 H11 119.5 . . ? C11 C12 C13 118.6(7) . . ? C11 C12 C14 120.9(7) . . ? C13 C12 C14 120.6(8) . . ? C8 C13 C12 121.2(7) . . ? C8 C13 H13 119.4 . . ? C12 C13 H13 119.4 . . ? N15 C14 C12 113.4(6) . . ? N15 C14 H14A 108.9 . . ? C12 C14 H14A 108.9 . . ? N15 C14 H14B 108.9 . . ? C12 C14 H14B 108.9 . . ? H14A C14 H14B 107.7 . . ? C16 N15 C19 107.0(6) . . ? C16 N15 C14 126.4(7) . . ? C19 N15 C14 126.5(7) . . ? N17 C16 N15 111.4(7) . . ? N17 C16 H16 124.3 . . ? N15 C16 H16 124.3 . . ? C16 N17 C18 105.7(7) . . ? C16 N17 Cu1 128.0(5) . 1_565 ? C18 N17 Cu1 126.1(5) . 1_565 ? C19 C18 N17 109.1(7) . . ? C19 C18 H18 125.5 . . ? N17 C18 H18 125.5 . . ? C18 C19 N15 106.8(7) . . ? C18 C19 H19 126.6 . . ? N15 C19 H19 126.6 . . ? C21 O20 C24 105.0(7) . . ? C21 O20 Cu2 128.1(6) . . ? C24 O20 Cu2 126.9(6) . . ? O20 C21 N22 111.2(7) . . ? O20 C21 H21 124.4 . . ? N22 C21 H21 124.4 . . ? C21 N22 C23 107.1(7) . . ? C21 N22 C25 126.2(7) . . ? C23 N22 C25 126.7(7) . . ? C24 C23 N22 106.4(8) . . ? C24 C23 H23 126.8 . . ? N22 C23 H23 126.8 . . ? C23 C24 O20 110.2(8) . . ? C23 C24 H24 124.9 . . ? O20 C24 H24 124.9 . . ? N22 C25 C26 112.9(7) . . ? N22 C25 H25A 109.0 . . ? C26 C25 H25A 109.0 . . ? N22 C25 H25B 109.0 . . ? C26 C25 H25B 109.0 . . ? H25A C25 H25B 107.8 . . ? C27 C26 C31 118.9(8) . . ? C27 C26 C25 121.2(8) . . ? C31 C26 C25 119.9(8) . . ? C26 C27 C28 121.2(8) . . ? C26 C27 H27 119.4 . . ? C28 C27 H27 119.4 . . ? C29 C28 C27 119.0(8) . . ? C29 C28 C32 120.4(8) . . ? C27 C28 C32 120.6(8) . . ? C28 C29 C30 120.3(9) . . ? C28 C29 H29 119.9 . . ? C30 C29 H29 119.9 . . ? C31 C30 C29 119.6(9) . . ? C31 C30 H30 120.2 . . ? C29 C30 H30 120.2 . . ? C30 C31 C26 121.1(9) . . ? C30 C31 H31 119.5 . . ? C26 C31 H31 119.5 . . ? N33 C32 C28 112.9(7) . . ? N33 C32 H32A 109.0 . . ? C28 C32 H32A 109.0 . . ? N33 C32 H32B 109.0 . . ? C28 C32 H32B 109.0 . . ? H32A C32 H32B 107.8 . . ? C34 N33 C37 107.9(7) . . ? C34 N33 C32 126.1(7) . . ? C37 N33 C32 126.0(7) . . ? N35 C34 N33 111.3(7) . . ? N35 C34 H34 124.3 . . ? N33 C34 H34 124.4 . . ? C34 N35 C36 105.5(7) . . ? C34 N35 Cu2 126.2(6) . 1_565 ? C36 N35 Cu2 127.7(5) . 1_565 ? C37 C36 N35 109.4(7) . . ? C37 C36 H36 125.3 . . ? N35 C36 H36 125.3 . . ? C36 C37 N33 105.9(7) . . ? C36 C37 H37 127.1 . . ? N33 C37 H37 127.1 . . ? O40 N38 O39 121.4(7) . . ? O40 N38 O41 119.9(7) . . ? O39 N38 O41 118.6(7) . . ? O43 N42 O45 120.3(8) . . ? O43 N42 O44 120.7(7) . . ? O45 N42 O44 119.0(8) . . ? C47 O46 H46 109.5 . . ? O46 C47 H47A 109.5 . . ? O46 C47 H47B 109.5 . . ? H47A C47 H47B 109.5 . . ? O46 C47 H47C 109.5 . . ? H47A C47 H47C 109.5 . . ? H47B C47 H47C 109.5 . . ? H48A O48 H48B 105(8) . . ? H49B O49 H49A 99(3) . . ? 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 N17 Cu1 N2 C3 -26.4(7) 1_545 . . . ? N17 Cu1 N2 C3 153.6(7) 2_676 . . . ? N17 Cu1 N2 C6 159.5(6) 1_545 . . . ? N17 Cu1 N2 C6 -20.5(6) 2_676 . . . ? C6 N2 C3 N4 -0.7(9) . . . . ? Cu1 N2 C3 N4 -175.7(5) . . . . ? N2 C3 N4 C5 0.6(9) . . . . ? N2 C3 N4 C7 -179.5(7) . . . . ? C3 N4 C5 C6 -0.2(9) . . . . ? C7 N4 C5 C6 179.9(7) . . . . ? N4 C5 C6 N2 -0.2(9) . . . . ? C3 N2 C6 C5 0.6(9) . . . . ? Cu1 N2 C6 C5 175.7(5) . . . . ? C3 N4 C7 C8 112.5(9) . . . . ? C5 N4 C7 C8 -67.5(10) . . . . ? N4 C7 C8 C9 -85.9(9) . . . . ? N4 C7 C8 C13 97.7(9) . . . . ? C13 C8 C9 C10 -0.3(12) . . . . ? C7 C8 C9 C10 -176.7(7) . . . . ? C8 C9 C10 C11 0.9(12) . . . . ? C9 C10 C11 C12 -0.6(13) . . . . ? C10 C11 C12 C13 -0.3(12) . . . . ? C10 C11 C12 C14 178.1(8) . . . . ? C9 C8 C13 C12 -0.7(12) . . . . ? C7 C8 C13 C12 175.8(7) . . . . ? C11 C12 C13 C8 1.0(11) . . . . ? C14 C12 C13 C8 -177.4(7) . . . . ? C11 C12 C14 N15 100.6(9) . . . . ? C13 C12 C14 N15 -81.0(10) . . . . ? C12 C14 N15 C16 117.0(8) . . . . ? C12 C14 N15 C19 -67.0(10) . . . . ? C19 N15 C16 N17 0.4(8) . . . . ? C14 N15 C16 N17 177.0(7) . . . . ? N15 C16 N17 C18 0.3(8) . . . . ? N15 C16 N17 Cu1 175.3(5) . . . 1_565 ? C16 N17 C18 C19 -0.9(8) . . . . ? Cu1 N17 C18 C19 -176.0(5) 1_565 . . . ? N17 C18 C19 N15 1.1(8) . . . . ? C16 N15 C19 C18 -0.9(8) . . . . ? C14 N15 C19 C18 -177.5(7) . . . . ? N35 Cu2 O20 C21 17.8(7) 1_545 . . . ? N35 Cu2 O20 C21 -162.2(7) 2_675 . . . ? N35 Cu2 O20 C24 -163.3(8) 1_545 . . . ? N35 Cu2 O20 C24 16.7(8) 2_675 . . . ? C24 O20 C21 N22 -1.2(10) . . . . ? Cu2 O20 C21 N22 177.8(5) . . . . ? O20 C21 N22 C23 1.1(10) . . . . ? O20 C21 N22 C25 179.9(7) . . . . ? C21 N22 C23 C24 -0.5(10) . . . . ? C25 N22 C23 C24 -179.3(8) . . . . ? N22 C23 C24 O20 -0.2(11) . . . . ? C21 O20 C24 C23 0.9(11) . . . . ? Cu2 O20 C24 C23 -178.2(6) . . . . ? C21 N22 C25 C26 85.3(10) . . . . ? C23 N22 C25 C26 -96.2(10) . . . . ? N22 C25 C26 C27 106.5(9) . . . . ? N22 C25 C26 C31 -74.4(10) . . . . ? C31 C26 C27 C28 -0.9(12) . . . . ? C25 C26 C27 C28 178.2(8) . . . . ? C26 C27 C28 C29 0.7(12) . . . . ? C26 C27 C28 C32 -177.2(7) . . . . ? C27 C28 C29 C30 0.5(13) . . . . ? C32 C28 C29 C30 178.4(8) . . . . ? C28 C29 C30 C31 -1.4(14) . . . . ? C29 C30 C31 C26 1.1(14) . . . . ? C27 C26 C31 C30 0.0(13) . . . . ? C25 C26 C31 C30 -179.1(8) . . . . ? C29 C28 C32 N33 70.0(11) . . . . ? C27 C28 C32 N33 -112.2(9) . . . . ? C28 C32 N33 C34 93.8(10) . . . . ? C28 C32 N33 C37 -87.4(10) . . . . ? C37 N33 C34 N35 0.5(9) . . . . ? C32 N33 C34 N35 179.5(7) . . . . ? N33 C34 N35 C36 0.0(9) . . . . ? N33 C34 N35 Cu2 -171.8(5) . . . 1_565 ? C34 N35 C36 C37 -0.5(9) . . . . ? Cu2 N35 C36 C37 171.2(5) 1_565 . . . ? N35 C36 C37 N33 0.7(9) . . . . ? C34 N33 C37 C36 -0.7(8) . . . . ? C32 N33 C37 C36 -179.8(7) . . . . ? _diffrn_measured_fraction_theta_max 0.933 _diffrn_reflns_theta_full 26.50 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 1.751 _refine_diff_density_min -0.600 _refine_diff_density_rms 0.117 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA O46 H46 O39 1_555 0.84 2.42 3.215(9) 158 O46 H46 O40 1_555 0.84 2.09 2.826(9) 146 O48 H48a O49 1_555 0.99(2) 1.72(3) 2.69(2) 166(9) O48 H48B O45 1_555 0.99(6) 1.98(11) 2.831(12) 142(14) O49 H49B O41 1_555 1.08(6) 1.85(5) 2.82(2) 148(6) C3 H3 O44 1_555 0.95 2.45 3.290(11) 147 C5 H5 O39 1_565 0.95 2.44 3.375(10) 166 C6 H6 O39 2_666 0.95 2.49 3.107(11) 123 C7 H7A O44 1_555 0.99 2.56 3.456(10) 150 C16 H16 O45 1_565 0.95 2.46 3.223(11) 138 C21 H21 O43 1_655 0.95 2.53 3.349(11) 144 C23 H23 O41 1_565 0.95 2.46 3.317(12) 150 C25 H25A O44 1_655 0.99 2.41 3.368(11) 164 C32 H32A O40 1_565 0.99 2.58 3.394(13) 140 C34 H34 O40 1_565 0.95 2.41 3.237(11) 145 # Attachment '8.CIF' data_VIII _database_code_depnum_ccdc_archive 'CCDC 681415' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common cNO3 _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H16 Cu N6 O7' _chemical_formula_weight 443.87 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.841(4) _cell_length_b 8.311(3) _cell_length_c 21.919(8) _cell_angle_alpha 90.00 _cell_angle_beta 101.047(7) _cell_angle_gamma 90.00 _cell_volume 1759.4(11) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1111 _cell_measurement_theta_min 2.474 _cell_measurement_theta_max 21.369 _exptl_crystal_description plate _exptl_crystal_colour blue _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.676 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 908 _exptl_absorpt_coefficient_mu 1.295 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8196 _exptl_absorpt_correction_T_max 0.9622 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area-detector' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10495 _diffrn_reflns_av_R_equivalents 0.0655 _diffrn_reflns_av_sigmaI/netI 0.0918 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 28.31 _reflns_number_total 4040 _reflns_number_gt 2712 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour 2001)' _computing_publication_material ? _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^)+(0.0659P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4040 _refine_ls_number_parameters 261 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.1086 _refine_ls_R_factor_gt 0.0673 _refine_ls_wR_factor_ref 0.1480 _refine_ls_wR_factor_gt 0.1313 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.32405(5) 0.25469(7) 0.44455(2) 0.01635(17) Uani 1 1 d . . . N1 N 0.2288(4) 0.3568(4) 0.50511(16) 0.0164(8) Uani 1 1 d . . . C2 C 0.2572(4) 0.4987(5) 0.5313(2) 0.0187(10) Uani 1 1 d . . . H2 H 0.3291 0.5673 0.5234 0.022 Uiso 1 1 calc R . . N3 N 0.1729(4) 0.5343(4) 0.57024(16) 0.0168(8) Uani 1 1 d . . . C4 C 0.0839(5) 0.4074(5) 0.5702(2) 0.0196(10) Uani 1 1 d . . . H4 H 0.0124 0.3976 0.5936 0.023 Uiso 1 1 calc R . . C5 C 0.1192(4) 0.2992(5) 0.5299(2) 0.0164(9) Uani 1 1 d . . . H5 H 0.0751 0.1982 0.5200 0.020 Uiso 1 1 calc R . . C6 C 0.1743(5) 0.6817(5) 0.6073(2) 0.0195(10) Uani 1 1 d . . . H6A H 0.0787 0.7236 0.6028 0.023 Uiso 1 1 calc R . . H6B H 0.2309 0.7645 0.5913 0.023 Uiso 1 1 calc R . . C7 C 0.2324(5) 0.6518(5) 0.6751(2) 0.0169(9) Uani 1 1 d . . . C8 C 0.1457(4) 0.6730(5) 0.7181(2) 0.0181(10) Uani 1 1 d . . . H8 H 0.0523 0.7058 0.7044 0.022 Uiso 1 1 calc R . . C9 C 0.1970(5) 0.6455(5) 0.7817(2) 0.0180(10) Uani 1 1 d . . . C10 C 0.3338(5) 0.5993(5) 0.8010(2) 0.0231(11) Uani 1 1 d . . . H10 H 0.3686 0.5788 0.8438 0.028 Uiso 1 1 calc R . . C11 C 0.4200(5) 0.5829(5) 0.7583(2) 0.0243(11) Uani 1 1 d . . . H11 H 0.5144 0.5540 0.7720 0.029 Uiso 1 1 calc R . . C12 C 0.3686(5) 0.6085(5) 0.6958(2) 0.0215(10) Uani 1 1 d . . . H12 H 0.4280 0.5962 0.6667 0.026 Uiso 1 1 calc R . . C13 C 0.1021(5) 0.6693(5) 0.8275(2) 0.0210(10) Uani 1 1 d . . . H13A H 0.1591 0.6926 0.8689 0.025 Uiso 1 1 calc R . . H13B H 0.0431 0.7645 0.8146 0.025 Uiso 1 1 calc R . . N14 N 0.0121(4) 0.5309(4) 0.83323(17) 0.0189(8) Uani 1 1 d . . . C15 C -0.0029(5) 0.4620(5) 0.8867(2) 0.0190(10) Uani 1 1 d . . . H15 H 0.0518 0.4876 0.9261 0.023 Uiso 1 1 calc R . . N16 N -0.1031(4) 0.3542(4) 0.87793(16) 0.0195(8) Uani 1 1 d . . . C17 C -0.1544(5) 0.3548(6) 0.8141(2) 0.0221(10) Uani 1 1 d . . . H17 H -0.2279 0.2892 0.7933 0.027 Uiso 1 1 calc R . . C18 C -0.0838(5) 0.4627(6) 0.7866(2) 0.0232(11) Uani 1 1 d . . . H18 H -0.0975 0.4869 0.7435 0.028 Uiso 1 1 calc R . . N19 N 0.1780(4) -0.0321(5) 0.44319(19) 0.0212(9) Uani 1 1 d . . . O20 O 0.0974(3) 0.0551(4) 0.40718(17) 0.0334(9) Uani 1 1 d . . . O21 O 0.1620(4) -0.1771(4) 0.44846(19) 0.0383(10) Uani 1 1 d . . . O22 O 0.2868(3) 0.0327(4) 0.47660(14) 0.0200(7) Uani 1 1 d . . . N23 N 0.2846(4) 0.5253(5) 0.37183(17) 0.0197(8) Uani 1 1 d . . . O24 O 0.3025(4) 0.6498(4) 0.34488(16) 0.0330(9) Uani 1 1 d . . . O25 O 0.1767(3) 0.4429(4) 0.35939(14) 0.0230(7) Uani 1 1 d . . . O26 O 0.3834(3) 0.4728(4) 0.41584(14) 0.0191(7) Uani 1 1 d . . . O27 O 0.5251(3) 0.2440(4) 0.51521(14) 0.0216(7) Uani 1 1 d D . . H27A H 0.600(4) 0.162(5) 0.521(3) 0.09(2) Uiso 1 1 d D . . H27B H 0.552(5) 0.320(5) 0.5501(18) 0.08(2) Uiso 1 1 d 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 0.0165(3) 0.0216(3) 0.0114(3) -0.0012(3) 0.00388(19) -0.0024(2) N1 0.018(2) 0.0187(19) 0.0114(18) -0.0005(16) 0.0009(15) 0.0010(16) C2 0.016(2) 0.026(2) 0.016(2) 0.003(2) 0.0069(19) -0.0011(19) N3 0.019(2) 0.022(2) 0.0095(19) -0.0010(16) 0.0036(15) 0.0003(16) C4 0.018(2) 0.028(3) 0.014(2) -0.001(2) 0.0050(18) -0.008(2) C5 0.013(2) 0.021(2) 0.015(2) 0.0049(18) 0.0020(18) -0.0035(17) C6 0.023(2) 0.020(2) 0.017(2) 0.003(2) 0.0045(19) 0.000(2) C7 0.021(2) 0.013(2) 0.017(2) -0.0008(19) 0.0025(18) -0.0038(18) C8 0.013(2) 0.023(2) 0.019(2) -0.004(2) 0.0048(18) -0.0002(19) C9 0.025(2) 0.016(2) 0.014(2) -0.0015(19) 0.0067(19) -0.0042(19) C10 0.029(3) 0.023(2) 0.015(2) 0.002(2) -0.001(2) -0.005(2) C11 0.017(2) 0.026(3) 0.028(3) -0.002(2) 0.001(2) 0.000(2) C12 0.023(2) 0.025(3) 0.020(2) -0.007(2) 0.010(2) -0.003(2) C13 0.030(3) 0.023(2) 0.011(2) -0.002(2) 0.0070(19) -0.006(2) N14 0.021(2) 0.024(2) 0.0120(19) 0.0002(17) 0.0033(15) 0.0007(17) C15 0.021(2) 0.025(2) 0.012(2) 0.001(2) 0.0036(18) 0.002(2) N16 0.020(2) 0.026(2) 0.013(2) 0.0022(17) 0.0034(16) 0.0007(17) C17 0.025(3) 0.025(3) 0.016(2) 0.000(2) 0.003(2) 0.001(2) C18 0.026(3) 0.033(3) 0.011(2) 0.002(2) 0.0023(19) 0.004(2) N19 0.016(2) 0.024(2) 0.026(2) -0.0038(19) 0.0104(17) 0.0010(17) O20 0.0224(19) 0.034(2) 0.039(2) -0.0074(18) -0.0061(16) 0.0038(16) O21 0.035(2) 0.0225(19) 0.061(3) -0.005(2) 0.016(2) -0.0099(16) O22 0.0174(16) 0.0272(17) 0.0147(16) -0.0029(14) 0.0013(13) -0.0062(14) N23 0.025(2) 0.026(2) 0.0092(19) -0.0043(17) 0.0071(16) -0.0006(18) O24 0.036(2) 0.034(2) 0.029(2) 0.0114(18) 0.0067(17) -0.0063(17) O25 0.0206(17) 0.0316(18) 0.0168(17) 0.0003(15) 0.0036(13) -0.0035(15) O26 0.0167(16) 0.0276(17) 0.0124(16) 0.0021(14) 0.0010(13) 0.0001(14) O27 0.0184(16) 0.0264(17) 0.0181(16) 0.0005(16) -0.0014(13) -0.0030(16) _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 1.959(3) . ? Cu1 N16 1.966(4) 4_665 ? Cu1 O22 2.033(3) . ? Cu1 O26 2.041(3) . ? Cu1 O27 2.269(3) . ? N1 C2 1.318(5) . ? N1 C5 1.383(5) . ? C2 N3 1.332(5) . ? C2 H2 0.9500 . ? N3 C4 1.371(5) . ? N3 C6 1.469(5) . ? C4 C5 1.353(6) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C7 1.508(6) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C12 1.378(6) . ? C7 C8 1.398(6) . ? C8 C9 1.408(6) . ? C8 H8 0.9500 . ? C9 C10 1.385(6) . ? C9 C13 1.509(6) . ? C10 C11 1.385(6) . ? C10 H10 0.9500 . ? C11 C12 1.384(7) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 N14 1.471(6) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? N14 C15 1.338(5) . ? N14 C18 1.374(6) . ? C15 N16 1.319(6) . ? C15 H15 0.9500 . ? N16 C17 1.393(6) . ? N16 Cu1 1.966(4) 4_566 ? C17 C18 1.347(6) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? N19 O21 1.224(5) . ? N19 O20 1.240(5) . ? N19 O22 1.293(5) . ? N23 O24 1.221(5) . ? N23 O25 1.249(5) . ? N23 O26 1.306(5) . ? O27 H27A 0.99(4) . ? O27 H27B 0.99(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 N16 172.96(15) . 4_665 ? N1 Cu1 O22 91.02(13) . . ? N16 Cu1 O22 87.38(14) 4_665 . ? N1 Cu1 O26 91.51(13) . . ? N16 Cu1 O26 90.77(14) 4_665 . ? O22 Cu1 O26 173.87(12) . . ? N1 Cu1 O27 91.27(14) . . ? N16 Cu1 O27 95.44(14) 4_665 . ? O22 Cu1 O27 85.40(12) . . ? O26 Cu1 O27 88.95(12) . . ? C2 N1 C5 104.8(4) . . ? C2 N1 Cu1 126.5(3) . . ? C5 N1 Cu1 128.8(3) . . ? N1 C2 N3 111.8(4) . . ? N1 C2 H2 124.1 . . ? N3 C2 H2 124.1 . . ? C2 N3 C4 107.8(4) . . ? C2 N3 C6 126.8(4) . . ? C4 N3 C6 125.4(4) . . ? C5 C4 N3 105.5(4) . . ? C5 C4 H4 127.2 . . ? N3 C4 H4 127.2 . . ? C4 C5 N1 110.1(4) . . ? C4 C5 H5 125.0 . . ? N1 C5 H5 125.0 . . ? N3 C6 C7 111.7(4) . . ? N3 C6 H6A 109.3 . . ? C7 C6 H6A 109.3 . . ? N3 C6 H6B 109.3 . . ? C7 C6 H6B 109.3 . . ? H6A C6 H6B 107.9 . . ? C12 C7 C8 119.5(4) . . ? C12 C7 C6 121.9(4) . . ? C8 C7 C6 118.6(4) . . ? C7 C8 C9 119.8(4) . . ? C7 C8 H8 120.1 . . ? C9 C8 H8 120.1 . . ? C10 C9 C8 119.4(4) . . ? C10 C9 C13 121.5(4) . . ? C8 C9 C13 119.1(4) . . ? C9 C10 C11 120.4(4) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C12 C11 C10 119.9(4) . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C7 C12 C11 120.9(4) . . ? C7 C12 H12 119.5 . . ? C11 C12 H12 119.5 . . ? N14 C13 C9 114.5(4) . . ? N14 C13 H13A 108.6 . . ? C9 C13 H13A 108.6 . . ? N14 C13 H13B 108.6 . . ? C9 C13 H13B 108.6 . . ? H13A C13 H13B 107.6 . . ? C15 N14 C18 107.5(4) . . ? C15 N14 C13 125.4(4) . . ? C18 N14 C13 126.7(4) . . ? N16 C15 N14 111.6(4) . . ? N16 C15 H15 124.2 . . ? N14 C15 H15 124.2 . . ? C15 N16 C17 105.1(4) . . ? C15 N16 Cu1 125.0(3) . 4_566 ? C17 N16 Cu1 129.3(3) . 4_566 ? C18 C17 N16 109.5(4) . . ? C18 C17 H17 125.2 . . ? N16 C17 H17 125.2 . . ? C17 C18 N14 106.3(4) . . ? C17 C18 H18 126.9 . . ? N14 C18 H18 126.9 . . ? O21 N19 O20 123.9(4) . . ? O21 N19 O22 117.7(4) . . ? O20 N19 O22 118.5(4) . . ? N19 O22 Cu1 111.5(3) . . ? O24 N23 O25 123.7(4) . . ? O24 N23 O26 119.0(4) . . ? O25 N23 O26 117.3(4) . . ? N23 O26 Cu1 107.9(3) . . ? Cu1 O27 H27A 130(3) . . ? Cu1 O27 H27B 125(3) . . ? H27A O27 H27B 105(4) . . ? 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 O22 Cu1 N1 C2 148.8(4) . . . . ? O26 Cu1 N1 C2 -25.6(4) . . . . ? O27 Cu1 N1 C2 63.4(4) . . . . ? O22 Cu1 N1 C5 -31.1(4) . . . . ? O26 Cu1 N1 C5 154.5(4) . . . . ? O27 Cu1 N1 C5 -116.5(4) . . . . ? C5 N1 C2 N3 -0.4(5) . . . . ? Cu1 N1 C2 N3 179.6(3) . . . . ? N1 C2 N3 C4 0.5(5) . . . . ? N1 C2 N3 C6 -179.9(4) . . . . ? C2 N3 C4 C5 -0.4(5) . . . . ? C6 N3 C4 C5 -180.0(4) . . . . ? N3 C4 C5 N1 0.2(5) . . . . ? C2 N1 C5 C4 0.2(5) . . . . ? Cu1 N1 C5 C4 -179.9(3) . . . . ? C2 N3 C6 C7 -106.3(5) . . . . ? C4 N3 C6 C7 73.2(5) . . . . ? N3 C6 C7 C12 65.6(5) . . . . ? N3 C6 C7 C8 -116.1(4) . . . . ? C12 C7 C8 C9 -1.8(6) . . . . ? C6 C7 C8 C9 179.8(4) . . . . ? C7 C8 C9 C10 0.7(7) . . . . ? C7 C8 C9 C13 179.9(4) . . . . ? C8 C9 C10 C11 1.1(7) . . . . ? C13 C9 C10 C11 -178.1(4) . . . . ? C9 C10 C11 C12 -1.7(7) . . . . ? C8 C7 C12 C11 1.2(7) . . . . ? C6 C7 C12 C11 179.5(4) . . . . ? C10 C11 C12 C7 0.6(7) . . . . ? C10 C9 C13 N14 -97.9(5) . . . . ? C8 C9 C13 N14 83.0(5) . . . . ? C9 C13 N14 C15 129.6(4) . . . . ? C9 C13 N14 C18 -59.4(6) . . . . ? C18 N14 C15 N16 -0.5(5) . . . . ? C13 N14 C15 N16 172.0(4) . . . . ? N14 C15 N16 C17 0.3(5) . . . . ? N14 C15 N16 Cu1 -171.7(3) . . . 4_566 ? C15 N16 C17 C18 0.0(5) . . . . ? Cu1 N16 C17 C18 171.5(3) 4_566 . . . ? N16 C17 C18 N14 -0.2(5) . . . . ? C15 N14 C18 C17 0.4(5) . . . . ? C13 N14 C18 C17 -171.9(4) . . . . ? O21 N19 O22 Cu1 163.8(3) . . . . ? O20 N19 O22 Cu1 -15.1(4) . . . . ? N1 Cu1 O22 N19 96.5(3) . . . . ? N16 Cu1 O22 N19 -76.6(3) 4_665 . . . ? O27 Cu1 O22 N19 -172.3(3) . . . . ? O24 N23 O26 Cu1 -175.1(3) . . . . ? O25 N23 O26 Cu1 4.2(4) . . . . ? N1 Cu1 O26 N23 -87.8(3) . . . . ? N16 Cu1 O26 N23 85.6(3) 4_665 . . . ? O27 Cu1 O26 N23 -179.0(2) . . . . ? _diffrn_measured_fraction_theta_max 0.923 _diffrn_reflns_theta_full 26.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.629 _refine_diff_density_min -0.617 _refine_diff_density_rms 0.115 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA O27 H27a O22 3_656 0.99(4) 1.96(4) 2.936(5) 167(5) O27 H27a O21 3_656 0.99(4) 2.31(4) 3.080(5) 133(3) O27 H27b O26 3_666 0.99(4) 1.94(4) 2.848(5) 153(3) O27 H27b O24 3_666 0.99(4) 2.48(4) 3.327(5) 144(3) C2 H2 O27 3_666 0.95 2.39 3.323(5) 168 C4 H4 O21 3_556 0.95 2.56 3.051(6) 112 C5 H5 O21 3_556 0.95 2.56 3.069(6) 113 C6 H6A O20 3_566 0.99 2.51 3.422(6) 153 C15 H15 O22 2_556 0.95 2.43 3.377(6) 173 C18 H18 O25 3_566 0.95 2.32 3.251(5) 168