# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Catherine E. Housecroft' _publ_contact_author_email CATHERINE.HOUSECROFT@UNIBAS.CH _publ_section_title ; Structural diversity in the reactions of 4'-(pyridyl)-2,2':6',2"-terpyridine ligands and bis{4'-(4-pyridyl)-2,2':6',2"-terpyridine}iron(II) with copper(II) salts ; loop_ _publ_author_name 'Catherine E. Housecroft' 'Jonathon E. Beves' 'Edwin C. Constable' 'Silvio Decurtins' 'Emma L. Dunphy' ; T.D.Keene ; 'Markus Neuburger' 'Silvia Schaffner' 'Jennifer A. Zampese' # Attachment 'JB1232.CIF' data_3t _database_code_depnum_ccdc_archive 'CCDC 732261' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H15 Cl2 Cu N4, 4.75(H2 O), Cl' _chemical_formula_sum 'C20 H24.5 Cl3 Cu N4 O4.75' _chemical_formula_weight 566.83 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 triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.747(5) _cell_length_b 11.305(5) _cell_length_c 14.063(5) _cell_angle_alpha 102.087(5) _cell_angle_beta 96.866(5) _cell_angle_gamma 91.748(5) _cell_volume 1193.7(10) _cell_formula_units_Z 2 _cell_measurement_temperature 200(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 0.1 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.567 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 574 _exptl_absorpt_coefficient_mu 1.288 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 'Stoe IPDS' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21942 _diffrn_reflns_av_R_equivalents 0.0657 _diffrn_reflns_av_sigmaI/netI 0.0375 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_theta_max 28.50 _reflns_number_total 6000 _reflns_number_gt 5680 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Stoe IPDS' _computing_cell_refinement 'Stoe IPDS' _computing_data_reduction 'Stoe IPDS' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0568P)^2^+0.7500P] 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 6000 _refine_ls_number_parameters 337 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0419 _refine_ls_R_factor_gt 0.0394 _refine_ls_wR_factor_ref 0.1083 _refine_ls_wR_factor_gt 0.1064 _refine_ls_goodness_of_fit_ref 1.102 _refine_ls_restrained_S_all 1.101 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.1941(2) 0.15271(18) 1.13380(16) 0.0260(4) Uani 1 1 d . . . H1 H 0.1126 0.1031 1.0874 0.031 Uiso 1 1 calc R . . C2 C 0.1565(3) 0.1878(2) 1.22984(17) 0.0292(4) Uani 1 1 d . . . H2 H 0.0511 0.1630 1.2470 0.035 Uiso 1 1 calc R . . C3 C 0.2789(3) 0.2601(2) 1.29915(16) 0.0301(4) Uani 1 1 d . . . H3 H 0.2570 0.2843 1.3638 0.036 Uiso 1 1 calc R . . C4 C 0.4357(3) 0.2963(2) 1.27082(15) 0.0270(4) Uani 1 1 d . . . H4 H 0.5202 0.3441 1.3164 0.032 Uiso 1 1 calc R . . C5 C 0.4632(2) 0.25967(17) 1.17361(14) 0.0215(3) Uani 1 1 d . . . C6 C 0.6229(2) 0.29345(17) 1.13324(13) 0.0202(3) Uani 1 1 d . . . C7 C 0.7620(2) 0.36974(17) 1.18395(13) 0.0217(3) Uani 1 1 d . . . H7 H 0.7623 0.4063 1.2497 0.026 Uiso 1 1 calc R . . C8 C 0.9035(2) 0.39097(17) 1.13400(13) 0.0202(3) Uani 1 1 d . . . C9 C 0.9022(2) 0.33060(17) 1.03599(14) 0.0220(3) Uani 1 1 d . . . H9 H 0.9961 0.3409 1.0024 0.026 Uiso 1 1 calc R . . C10 C 0.7580(2) 0.25513(16) 0.98999(13) 0.0199(3) Uani 1 1 d . . . C11 C 0.7350(2) 0.18340(16) 0.88730(14) 0.0207(3) Uani 1 1 d . . . C12 C 0.8622(3) 0.17537(19) 0.82500(15) 0.0268(4) Uani 1 1 d . . . H12 H 0.9717 0.2143 0.8464 0.032 Uiso 1 1 calc R . . C13 C 0.8217(3) 0.1072(2) 0.72923(16) 0.0335(4) Uani 1 1 d . . . H13 H 0.9040 0.1001 0.6856 0.040 Uiso 1 1 calc R . . C14 C 0.6579(3) 0.0508(2) 0.70036(16) 0.0336(4) Uani 1 1 d . . . H14 H 0.6274 0.0072 0.6364 0.040 Uiso 1 1 calc R . . C15 C 0.5379(3) 0.05950(19) 0.76808(16) 0.0290(4) Uani 1 1 d . . . H15 H 0.4288 0.0192 0.7488 0.035 Uiso 1 1 calc R . . C16 C 1.0543(2) 0.47336(17) 1.18596(14) 0.0214(3) Uani 1 1 d . . . C17 C 1.2024(2) 0.48776(18) 1.13978(15) 0.0247(4) Uani 1 1 d . . . H17 H 1.2047 0.4491 1.0747 0.030 Uiso 1 1 calc R . . C18 C 1.3443(3) 0.55936(19) 1.19134(16) 0.0279(4) Uani 1 1 d . . . H18 H 1.4427 0.5686 1.1611 0.034 Uiso 1 1 calc R . . C19 C 1.0549(3) 0.5376(2) 1.28225(16) 0.0356(5) Uani 1 1 d . . . H19 H 0.9569 0.5329 1.3139 0.043 Uiso 1 1 calc R . . C20 C 1.2001(3) 0.6078(3) 1.33052(17) 0.0394(5) Uani 1 1 d . . . H20 H 1.2005 0.6497 1.3949 0.047 Uiso 1 1 calc R . . N1 N 0.3443(2) 0.18804(15) 1.10567(12) 0.0220(3) Uani 1 1 d . . . H1' H 1.430(4) 0.656(3) 1.317(2) 0.026 Uiso 1 1 d . . . N2 N 0.62169(19) 0.24179(14) 1.03824(11) 0.0201(3) Uani 1 1 d . . . N3 N 0.5760(2) 0.12414(15) 0.85965(12) 0.0225(3) Uani 1 1 d . . . N4 N 1.3408(2) 0.61576(18) 1.28490(14) 0.0301(4) Uani 1 1 d . . . Cl1 Cl 0.21521(7) 0.00134(5) 0.89962(4) 0.03321(12) Uani 1 1 d . . . Cl2 Cl 0.28758(6) 0.33644(4) 0.91014(3) 0.02420(11) Uani 1 1 d . . . Cl3 Cl -0.15157(12) 0.14813(10) 0.41595(8) 0.0703(2) Uani 1 1 d . . . Cu1 Cu 0.41426(3) 0.14851(2) 0.966810(16) 0.02087(8) Uani 1 1 d . . . O2 O 0.3136(2) 0.3007(2) 0.68757(13) 0.0444(4) Uani 1 1 d D . . H200 H 0.274(5) 0.236(2) 0.645(2) 0.053 Uiso 1 1 d D . . H201 H 0.291(5) 0.307(3) 0.7473(16) 0.053 Uiso 1 1 d D . . O3 O -0.4795(3) 0.2325(2) 0.52113(16) 0.0491(5) Uani 1 1 d D . . H300 H -0.411(4) 0.194(3) 0.484(2) 0.059 Uiso 1 1 d D . . H301 H -0.556(4) 0.171(3) 0.508(3) 0.059 Uiso 1 1 d D . . O1 O 0.2070(3) 0.1051(3) 0.5326(2) 0.0627(6) Uani 1 1 d D . . H400 H 0.200(6) 0.032(2) 0.544(3) 0.075 Uiso 1 1 d D . . H401 H 0.104(3) 0.123(4) 0.511(3) 0.075 Uiso 1 1 d D . . O4 O 1.0307(18) 0.5963(11) 0.5371(8) 0.070(3) Uani 0.25 1 d P A 4 O5 O 1.1468(8) 0.5655(5) 0.5605(4) 0.0594(12) Uani 0.50 1 d P B 1 O6 O 1.2880(8) 0.4688(5) 0.5813(5) 0.0784(16) Uani 0.50 1 d P C 2 O7 O 1.4468(7) 0.4760(4) 0.5147(4) 0.0641(12) Uani 0.50 1 d P . 3 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0165(8) 0.0273(9) 0.0355(10) 0.0109(8) 0.0026(7) -0.0042(7) C2 0.0197(9) 0.0331(10) 0.0386(11) 0.0144(8) 0.0089(8) -0.0028(7) C3 0.0260(10) 0.0388(11) 0.0289(9) 0.0115(8) 0.0102(8) -0.0004(8) C4 0.0209(9) 0.0329(10) 0.0268(9) 0.0066(7) 0.0032(7) -0.0039(7) C5 0.0148(7) 0.0241(8) 0.0268(9) 0.0085(7) 0.0025(6) -0.0025(6) C6 0.0146(7) 0.0234(8) 0.0230(8) 0.0063(6) 0.0027(6) -0.0006(6) C7 0.0166(8) 0.0258(8) 0.0214(8) 0.0029(6) 0.0029(6) -0.0035(6) C8 0.0138(7) 0.0243(8) 0.0221(8) 0.0046(6) 0.0015(6) -0.0028(6) C9 0.0140(7) 0.0271(9) 0.0247(8) 0.0053(7) 0.0034(6) -0.0019(6) C10 0.0150(7) 0.0219(8) 0.0221(8) 0.0034(6) 0.0018(6) 0.0007(6) C11 0.0163(8) 0.0207(8) 0.0238(8) 0.0029(6) 0.0005(6) 0.0013(6) C12 0.0217(9) 0.0300(9) 0.0274(9) 0.0026(7) 0.0047(7) 0.0008(7) C13 0.0334(11) 0.0374(11) 0.0278(10) -0.0007(8) 0.0105(8) 0.0017(9) C14 0.0371(11) 0.0316(10) 0.0267(9) -0.0047(8) 0.0022(8) 0.0004(8) C15 0.0245(9) 0.0262(9) 0.0313(10) -0.0024(8) -0.0015(7) 0.0013(7) C16 0.0150(8) 0.0247(8) 0.0236(8) 0.0048(7) 0.0006(6) -0.0026(6) C17 0.0192(8) 0.0254(9) 0.0289(9) 0.0032(7) 0.0056(7) -0.0029(7) C18 0.0173(8) 0.0284(9) 0.0389(11) 0.0089(8) 0.0051(7) -0.0039(7) C19 0.0264(10) 0.0505(13) 0.0254(9) -0.0015(9) 0.0066(8) -0.0162(9) C20 0.0344(11) 0.0529(14) 0.0251(10) 0.0011(9) 0.0000(8) -0.0211(10) N1 0.0150(7) 0.0235(7) 0.0278(8) 0.0073(6) 0.0026(6) -0.0030(5) N2 0.0144(6) 0.0224(7) 0.0223(7) 0.0034(6) 0.0007(5) -0.0012(5) N3 0.0166(7) 0.0220(7) 0.0267(8) 0.0014(6) 0.0003(6) 0.0004(5) N4 0.0208(8) 0.0344(9) 0.0330(9) 0.0098(7) -0.0063(7) -0.0117(7) Cl1 0.0255(2) 0.0266(2) 0.0430(3) 0.0018(2) -0.0007(2) -0.01095(18) Cl2 0.0206(2) 0.0261(2) 0.0279(2) 0.00738(16) 0.00819(16) 0.00201(16) Cl3 0.0537(5) 0.0781(6) 0.0805(6) 0.0110(5) 0.0244(4) 0.0038(4) Cu1 0.01402(12) 0.02136(12) 0.02526(13) 0.00232(8) 0.00067(8) -0.00388(8) O2 0.0307(9) 0.0688(13) 0.0295(8) 0.0032(8) 0.0043(7) -0.0121(8) O3 0.0373(10) 0.0528(11) 0.0482(11) -0.0094(9) 0.0085(8) -0.0115(8) O1 0.0471(12) 0.0670(15) 0.0639(14) -0.0029(12) 0.0026(11) -0.0230(11) O4 0.080(8) 0.070(7) 0.064(6) 0.020(5) 0.009(6) -0.009(6) O5 0.082(4) 0.055(3) 0.049(2) 0.024(2) 0.021(2) -0.002(2) O6 0.085(4) 0.058(3) 0.097(4) 0.020(3) 0.025(3) 0.012(3) O7 0.076(3) 0.048(2) 0.068(3) 0.013(2) 0.004(2) -0.005(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.349(2) . ? C1 C2 1.394(3) . ? C1 H1 0.9300 . ? C2 C3 1.384(3) . ? C2 H2 0.9300 . ? C3 C4 1.399(3) . ? C3 H3 0.9300 . ? C4 C5 1.387(3) . ? C4 H4 0.9300 . ? C5 N1 1.355(2) . ? C5 C6 1.493(2) . ? C6 N2 1.340(2) . ? C6 C7 1.384(3) . ? C7 C8 1.411(2) . ? C7 H7 0.9300 . ? C8 C9 1.403(3) . ? C8 C16 1.487(3) . ? C9 C10 1.390(3) . ? C9 H9 0.9300 . ? C10 N2 1.343(2) . ? C10 C11 1.488(3) . ? C11 N3 1.357(2) . ? C11 C12 1.388(3) . ? C12 C13 1.398(3) . ? C12 H12 0.9300 . ? C13 C14 1.379(3) . ? C13 H13 0.9300 . ? C14 C15 1.400(3) . ? C14 H14 0.9300 . ? C15 N3 1.335(3) . ? C15 H15 0.9300 . ? C16 C19 1.395(3) . ? C16 C17 1.406(3) . ? C17 C18 1.377(3) . ? C17 H17 0.9300 . ? C18 N4 1.340(3) . ? C18 H18 0.9300 . ? C19 C20 1.376(3) . ? C19 H19 0.9300 . ? C20 N4 1.339(3) . ? C20 H20 0.9300 . ? N1 Cu1 2.0516(18) . ? N2 Cu1 1.9418(18) . ? N3 Cu1 2.0534(18) . ? N4 H1' 0.84(3) . ? Cl1 Cu1 2.2080(9) . ? Cl2 Cu1 2.6003(10) . ? O2 H200 0.865(18) . ? O2 H201 0.867(18) . ? O3 H300 0.857(18) . ? O3 H301 0.869(19) . ? O1 H400 0.882(19) . ? O1 H401 0.865(19) . ? O7 O7 1.137(10) 2_866 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 122.39(19) . . ? N1 C1 H1 118.8 . . ? C2 C1 H1 118.8 . . ? C3 C2 C1 118.81(18) . . ? C3 C2 H2 120.6 . . ? C1 C2 H2 120.6 . . ? C2 C3 C4 119.19(19) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C5 C4 C3 118.91(19) . . ? C5 C4 H4 120.5 . . ? C3 C4 H4 120.5 . . ? N1 C5 C4 122.08(17) . . ? N1 C5 C6 113.47(16) . . ? C4 C5 C6 124.45(17) . . ? N2 C6 C7 120.64(16) . . ? N2 C6 C5 112.96(16) . . ? C7 C6 C5 126.39(17) . . ? C6 C7 C8 118.73(17) . . ? C6 C7 H7 120.6 . . ? C8 C7 H7 120.6 . . ? C9 C8 C7 119.17(17) . . ? C9 C8 C16 120.65(16) . . ? C7 C8 C16 120.15(16) . . ? C10 C9 C8 118.75(16) . . ? C10 C9 H9 120.6 . . ? C8 C9 H9 120.6 . . ? N2 C10 C9 120.47(17) . . ? N2 C10 C11 113.44(16) . . ? C9 C10 C11 126.09(16) . . ? N3 C11 C12 122.38(18) . . ? N3 C11 C10 113.37(16) . . ? C12 C11 C10 124.25(17) . . ? C11 C12 C13 118.36(19) . . ? C11 C12 H12 120.8 . . ? C13 C12 H12 120.8 . . ? C14 C13 C12 119.0(2) . . ? C14 C13 H13 120.5 . . ? C12 C13 H13 120.5 . . ? C13 C14 C15 119.5(2) . . ? C13 C14 H14 120.2 . . ? C15 C14 H14 120.2 . . ? N3 C15 C14 121.7(2) . . ? N3 C15 H15 119.2 . . ? C14 C15 H15 119.2 . . ? C19 C16 C17 117.79(18) . . ? C19 C16 C8 121.37(17) . . ? C17 C16 C8 120.84(17) . . ? C18 C17 C16 119.68(19) . . ? C18 C17 H17 120.2 . . ? C16 C17 H17 120.2 . . ? N4 C18 C17 120.25(18) . . ? N4 C18 H18 119.9 . . ? C17 C18 H18 119.9 . . ? C20 C19 C16 120.2(2) . . ? C20 C19 H19 119.9 . . ? C16 C19 H19 119.9 . . ? N4 C20 C19 120.1(2) . . ? N4 C20 H20 119.9 . . ? C19 C20 H20 119.9 . . ? C1 N1 C5 118.60(17) . . ? C1 N1 Cu1 126.80(14) . . ? C5 N1 Cu1 114.57(12) . . ? C6 N2 C10 122.05(16) . . ? C6 N2 Cu1 119.17(12) . . ? C10 N2 Cu1 118.76(13) . . ? C15 N3 C11 118.96(17) . . ? C15 N3 Cu1 126.55(14) . . ? C11 N3 Cu1 114.48(13) . . ? C20 N4 C18 121.91(19) . . ? C20 N4 H1' 118.4(19) . . ? C18 N4 H1' 119.6(19) . . ? N2 Cu1 N1 79.55(7) . . ? N2 Cu1 N3 79.71(7) . . ? N1 Cu1 N3 157.90(7) . . ? N2 Cu1 Cl1 164.19(5) . . ? N1 Cu1 Cl1 98.79(5) . . ? N3 Cu1 Cl1 99.08(6) . . ? N2 Cu1 Cl2 92.38(6) . . ? N1 Cu1 Cl2 96.92(5) . . ? N3 Cu1 Cl2 91.47(5) . . ? Cl1 Cu1 Cl2 103.43(4) . . ? H200 O2 H201 118(4) . . ? H300 O3 H301 92(3) . . ? H400 O1 H401 108(4) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 28.50 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.638 _refine_diff_density_min -0.584 _refine_diff_density_rms 0.077 # start Validation Reply Form _vrf_PLAT430_3t ; PROBLEM: Short Inter D...A Contact O4 .. O4 .. 2.22 Ang. RESPONSE: Relates to a disordered water of partial occupancy ; # end Validation Reply Form # Attachment 'JB1236-2_new.CIF' data_jb1236 _database_code_depnum_ccdc_archive 'CCDC 732262' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H14 Cl2 Cu N4, 2(H2 O)' _chemical_formula_sum 'C20 H18 Cl2 Cu N4 O2' _chemical_formula_weight 480.83 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 Pcca _symmetry_space_group_name_Hall -P2a2ac loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z' '-x, y, -z+1/2' 'x+1/2, -y, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z' 'x, -y, z-1/2' '-x-1/2, y, z-1/2' _cell_length_a 11.090(2) _cell_length_b 8.0686(16) _cell_length_c 21.934(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1962.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 223(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 0.16 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.627 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 980 _exptl_absorpt_coefficient_mu 1.410 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8058 _exptl_absorpt_correction_T_max 0.9201 _exptl_absorpt_process_details '(Blessing 1951)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(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 'Stoe IPDS' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20874 _diffrn_reflns_av_R_equivalents 0.0475 _diffrn_reflns_av_sigmaI/netI 0.0171 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2264 _reflns_number_gt 2117 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Stoe IPDS' _computing_cell_refinement 'Stoe IPDS' _computing_data_reduction 'Stoe IPDS' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Restraints were used on solvent water hydrogens on o1 and o2 which were located from the difference map and not constrained by afix ; _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^)+(0.0261P)^2^+1.5427P] 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 2264 _refine_ls_number_parameters 141 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0349 _refine_ls_R_factor_gt 0.0316 _refine_ls_wR_factor_ref 0.0733 _refine_ls_wR_factor_gt 0.0719 _refine_ls_goodness_of_fit_ref 1.173 _refine_ls_restrained_S_all 1.173 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.09928(4) 0.77404(6) 0.37592(2) 0.02944(12) Uani 1 1 d . . . Cu1 Cu 0.2500 0.5000 0.364606(13) 0.02684(11) Uani 1 2 d S . . N1 N 0.10783(14) 0.3437(2) 0.38053(6) 0.0230(3) Uani 1 1 d . . . N2 N 0.2500 0.5000 0.45270(9) 0.0217(4) Uani 1 2 d S . . C1 C 0.04075(18) 0.2635(3) 0.33974(8) 0.0282(4) Uani 1 1 d . . . H1 H 0.0580 0.2783 0.2981 0.034 Uiso 1 1 calc R . . C2 C -0.05301(19) 0.1595(3) 0.35576(9) 0.0321(4) Uani 1 1 d . . . H2 H -0.0991 0.1055 0.3258 0.038 Uiso 1 1 calc R . . C3 C -0.07729(18) 0.1368(3) 0.41723(9) 0.0310(4) Uani 1 1 d . . . H3 H -0.1403 0.0665 0.4296 0.037 Uiso 1 1 calc R . . N3 N 0.2500 0.5000 0.77354(9) 0.0265(5) Uani 1 2 d S . . C4 C -0.00766(17) 0.2188(3) 0.46026(8) 0.0267(4) Uani 1 1 d . . . H4 H -0.0231 0.2054 0.5021 0.032 Uiso 1 1 calc R . . C5 C 0.08462(16) 0.3204(2) 0.44069(7) 0.0211(3) Uani 1 1 d . . . C6 C 0.16698(15) 0.4107(2) 0.48222(7) 0.0202(3) Uani 1 1 d . . . C7 C 0.16449(16) 0.4078(2) 0.54556(7) 0.0221(4) Uani 1 1 d . . . H7 H 0.1062 0.3449 0.5664 0.027 Uiso 1 1 calc R . . C8 C 0.2500 0.5000 0.57781(11) 0.0217(5) Uani 1 2 d S . . C9 C 0.2500 0.5000 0.64580(11) 0.0227(5) Uani 1 2 d S . . C10 C 0.1723(2) 0.4003(3) 0.67882(8) 0.0339(5) Uani 1 1 d . . . H10 H 0.1180 0.3301 0.6584 0.041 Uiso 1 1 calc R . . C11 C 0.1746(2) 0.4038(3) 0.74202(8) 0.0350(5) Uani 1 1 d . . . H11 H 0.1207 0.3356 0.7636 0.042 Uiso 1 1 calc R . . O1 O 0.2500 1.0000 0.47106(11) 0.0411(5) Uani 1 2 d SD . . H1' H 0.211(2) 0.949(3) 0.4463(11) 0.049 Uiso 1 1 d D . . O2 O 0.2500 1.0000 0.27506(14) 0.0664(9) Uani 1 2 d SD . . H2' H 0.202(3) 0.956(4) 0.2978(14) 0.080 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 Cl1 0.0313(2) 0.0342(3) 0.0227(2) -0.00278(17) 0.00222(17) 0.00061(19) Cu1 0.02989(18) 0.0429(2) 0.00772(15) 0.000 0.000 -0.00895(14) N1 0.0245(7) 0.0317(8) 0.0127(6) -0.0013(6) -0.0010(5) 0.0000(6) N2 0.0240(10) 0.0293(11) 0.0117(9) 0.000 0.000 0.0001(9) C1 0.0326(10) 0.0355(10) 0.0165(8) -0.0040(7) -0.0037(7) -0.0012(8) C2 0.0326(10) 0.0375(11) 0.0261(9) -0.0065(8) -0.0076(8) -0.0029(8) C3 0.0278(9) 0.0343(11) 0.0310(10) -0.0015(8) -0.0003(8) -0.0057(8) N3 0.0297(11) 0.0398(13) 0.0099(9) 0.000 0.000 0.0054(10) C4 0.0285(9) 0.0315(10) 0.0200(8) 0.0006(7) 0.0014(7) -0.0015(8) C5 0.0231(8) 0.0265(9) 0.0137(7) -0.0007(6) -0.0008(6) 0.0024(7) C6 0.0222(8) 0.0257(9) 0.0128(7) -0.0006(6) 0.0008(6) 0.0016(7) C7 0.0243(9) 0.0289(9) 0.0131(7) 0.0010(6) 0.0014(6) 0.0006(7) C8 0.0256(12) 0.0284(13) 0.0110(10) 0.000 0.000 0.0040(10) C9 0.0265(12) 0.0315(13) 0.0102(10) 0.000 0.000 0.0051(10) C10 0.0404(11) 0.0478(13) 0.0135(8) 0.0008(8) -0.0014(7) -0.0139(10) C11 0.0389(11) 0.0518(13) 0.0141(8) 0.0042(8) 0.0007(7) -0.0103(10) O1 0.0417(13) 0.0480(14) 0.0334(12) 0.000 0.000 -0.0060(11) O2 0.086(2) 0.066(2) 0.0473(17) 0.000 0.000 -0.0265(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N2 1.932(2) . ? Cu1 N3 1.998(2) 7_565 ? Cu1 N1 2.0488(16) 2_565 ? Cu1 N1 2.0488(16) . ? N1 C1 1.332(2) . ? N1 C5 1.357(2) . ? N2 C6 1.336(2) 2_565 ? N2 C6 1.336(2) . ? C1 C2 1.382(3) . ? C1 H1 0.9400 . ? C2 C3 1.387(3) . ? C2 H2 0.9400 . ? C3 C4 1.387(3) . ? C3 H3 0.9400 . ? N3 C11 1.334(2) . ? N3 C11 1.334(2) 2_565 ? N3 Cu1 1.998(2) 7_566 ? C4 C5 1.380(3) . ? C4 H4 0.9400 . ? C5 C6 1.482(2) . ? C6 C7 1.390(2) . ? C7 C8 1.397(2) . ? C7 H7 0.9400 . ? C8 C7 1.397(2) 2_565 ? C8 C9 1.491(3) . ? C9 C10 1.384(2) 2_565 ? C9 C10 1.384(2) . ? C10 C11 1.387(2) . ? C10 H10 0.9400 . ? C11 H11 0.9400 . ? O1 H1' 0.809(16) . ? O2 H2' 0.810(18) . ? 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 N3 180.0 . 7_565 ? N2 Cu1 N1 80.18(4) . 2_565 ? N3 Cu1 N1 99.82(4) 7_565 2_565 ? N2 Cu1 N1 80.18(4) . . ? N3 Cu1 N1 99.82(4) 7_565 . ? N1 Cu1 N1 160.36(8) 2_565 . ? C1 N1 C5 118.68(16) . . ? C1 N1 Cu1 127.92(13) . . ? C5 N1 Cu1 113.39(12) . . ? C6 N2 C6 122.0(2) 2_565 . ? C6 N2 Cu1 118.99(10) 2_565 . ? C6 N2 Cu1 118.99(10) . . ? N1 C1 C2 123.01(17) . . ? N1 C1 H1 118.5 . . ? C2 C1 H1 118.5 . . ? C1 C2 C3 118.25(18) . . ? C1 C2 H2 120.9 . . ? C3 C2 H2 120.9 . . ? C2 C3 C4 119.37(18) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C11 N3 C11 117.6(2) . 2_565 ? C11 N3 Cu1 121.22(11) . 7_566 ? C11 N3 Cu1 121.22(11) 2_565 7_566 ? C5 C4 C3 118.99(17) . . ? C5 C4 H4 120.5 . . ? C3 C4 H4 120.5 . . ? N1 C5 C4 121.69(16) . . ? N1 C5 C6 114.36(15) . . ? C4 C5 C6 123.94(15) . . ? N2 C6 C7 120.48(16) . . ? N2 C6 C5 113.08(15) . . ? C7 C6 C5 126.44(16) . . ? C6 C7 C8 118.92(17) . . ? C6 C7 H7 120.5 . . ? C8 C7 H7 120.5 . . ? C7 C8 C7 119.2(2) . 2_565 ? C7 C8 C9 120.41(11) . . ? C7 C8 C9 120.41(11) 2_565 . ? C10 C9 C10 116.9(2) 2_565 . ? C10 C9 C8 121.57(12) 2_565 . ? C10 C9 C8 121.57(12) . . ? C9 C10 C11 119.98(19) . . ? C9 C10 H10 120.0 . . ? C11 C10 H10 120.0 . . ? N3 C11 C10 122.80(19) . . ? N3 C11 H11 118.6 . . ? C10 C11 H11 118.6 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.373 _refine_diff_density_min -0.404 _refine_diff_density_rms 0.055 # Attachment 'JB1236-3_new.CIF' data_jb1236_3 _database_code_depnum_ccdc_archive 'CCDC 732263' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H14 Cl2 Cu N4, C H4 O, H2 O' _chemical_formula_sum 'C21 H20 Cl2 Cu N4 O2' _chemical_formula_weight 494.85 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.175(3) _cell_length_b 8.646(3) _cell_length_c 16.128(6) _cell_angle_alpha 95.35(3) _cell_angle_beta 99.39(3) _cell_angle_gamma 108.48(2) _cell_volume 1053.8(7) _cell_formula_units_Z 2 _cell_measurement_temperature 223(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 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.559 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 506 _exptl_absorpt_coefficient_mu 1.316 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6559 _exptl_absorpt_correction_T_max 0.8581 _exptl_absorpt_process_details '(Blessing 1951)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(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 'Stoe IPDS' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26209 _diffrn_reflns_av_R_equivalents 0.0660 _diffrn_reflns_av_sigmaI/netI 0.0357 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.59 _diffrn_reflns_theta_max 30.00 _reflns_number_total 6089 _reflns_number_gt 5750 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Stoe IPDS' _computing_cell_refinement 'Stoe IPDS' _computing_data_reduction 'Stoe IPDS' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Restraints were used on solvent water hydrogens attached to o1 which were located from the difference map and not constrained by afix ; _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^)+(0.0565P)^2^+0.3418P] 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 6089 _refine_ls_number_parameters 279 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0389 _refine_ls_R_factor_gt 0.0369 _refine_ls_wR_factor_ref 0.1020 _refine_ls_wR_factor_gt 0.1002 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.078 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 1.00970(2) 0.53587(2) 0.382022(12) 0.02965(7) Uani 1 1 d . . . Cl1 Cl 1.20729(6) 0.70298(5) 0.49197(3) 0.04006(11) Uani 1 1 d . . . Cl2 Cl 1.10926(6) 0.66429(5) 0.25279(3) 0.03813(10) Uani 1 1 d . . . N1 N 1.11455(18) 0.35220(16) 0.37015(9) 0.0300(2) Uani 1 1 d . . . N2 N 0.81396(16) 0.36562(15) 0.30574(8) 0.0276(2) Uani 1 1 d . . . N3 N 0.82183(17) 0.64529(16) 0.37602(8) 0.0295(2) Uani 1 1 d . . . N4 N 0.1510(2) -0.1910(2) -0.01478(11) 0.0490(4) Uani 1 1 d . . . C1 C 1.2735(2) 0.3558(2) 0.40895(11) 0.0358(3) Uani 1 1 d . . . H1 H 1.3470 0.4508 0.4469 0.043 Uiso 1 1 calc R . . C2 C 1.3346(2) 0.2245(2) 0.39548(13) 0.0410(4) Uani 1 1 d . . . H2 H 1.4468 0.2303 0.4239 0.049 Uiso 1 1 calc R . . C3 C 1.2270(3) 0.0857(2) 0.33951(14) 0.0444(4) Uani 1 1 d . . . H3 H 1.2649 -0.0049 0.3291 0.053 Uiso 1 1 calc R . . C4 C 1.0625(2) 0.0813(2) 0.29883(13) 0.0388(4) Uani 1 1 d . . . H4 H 0.9874 -0.0124 0.2604 0.047 Uiso 1 1 calc R . . C5 C 1.0096(2) 0.21620(19) 0.31529(10) 0.0297(3) Uani 1 1 d . . . C6 C 0.83686(19) 0.22540(18) 0.27673(10) 0.0280(3) Uani 1 1 d . . . C7 C 0.7066(2) 0.10778(19) 0.21585(10) 0.0310(3) Uani 1 1 d . . . H7 H 0.7210 0.0082 0.1959 0.037 Uiso 1 1 calc R . . C8 C 0.5530(2) 0.14079(18) 0.18468(10) 0.0295(3) Uani 1 1 d . . . C9 C 0.5313(2) 0.28803(19) 0.21762(10) 0.0307(3) Uani 1 1 d . . . H9 H 0.4277 0.3109 0.1984 0.037 Uiso 1 1 calc R . . C10 C 0.66673(19) 0.39815(18) 0.27914(9) 0.0280(3) Uani 1 1 d . . . C11 C 0.6699(2) 0.55952(18) 0.32080(10) 0.0285(3) Uani 1 1 d . . . C12 C 0.5318(2) 0.6207(2) 0.30575(12) 0.0360(3) Uani 1 1 d . . . H12 H 0.4265 0.5589 0.2673 0.043 Uiso 1 1 calc R . . C13 C 0.5517(2) 0.7747(2) 0.34843(13) 0.0406(4) Uani 1 1 d . . . H13 H 0.4592 0.8177 0.3398 0.049 Uiso 1 1 calc R . . C14 C 0.7075(3) 0.8633(2) 0.40333(13) 0.0401(4) Uani 1 1 d . . . H14 H 0.7243 0.9686 0.4321 0.048 Uiso 1 1 calc R . . C15 C 0.8402(2) 0.7943(2) 0.41567(11) 0.0354(3) Uani 1 1 d . . . H15 H 0.9470 0.8549 0.4534 0.043 Uiso 1 1 calc R . . C16 C 0.4148(2) 0.0248(2) 0.11601(10) 0.0318(3) Uani 1 1 d . . . C17 C 0.3724(3) -0.1449(2) 0.11070(12) 0.0413(4) Uani 1 1 d . . . H17 H 0.4330 -0.1903 0.1508 0.050 Uiso 1 1 calc R . . C18 C 0.2386(3) -0.2465(2) 0.04487(13) 0.0496(5) Uani 1 1 d . . . H18 H 0.2086 -0.3613 0.0427 0.059 Uiso 1 1 calc R . . C19 C 0.1946(3) -0.0282(3) -0.01008(12) 0.0467(4) Uani 1 1 d . . . H19 H 0.1349 0.0133 -0.0526 0.056 Uiso 1 1 calc R . . C20 C 0.3227(3) 0.0836(2) 0.05382(12) 0.0412(4) Uani 1 1 d . . . H20 H 0.3470 0.1976 0.0551 0.049 Uiso 1 1 calc R . . O100 O 0.7917(3) 0.7432(2) 0.15444(13) 0.0672(5) Uani 1 1 d . . . H100 H 0.8843 0.7332 0.1791 0.101 Uiso 1 1 calc R . . C200 C 0.7065(5) 0.6117(4) 0.08954(17) 0.0720(8) Uani 1 1 d . . . H20D H 0.5870 0.6090 0.0696 0.108 Uiso 1 1 calc R . . H20E H 0.7039 0.5096 0.1105 0.108 Uiso 1 1 calc R . . H20F H 0.7690 0.6244 0.0430 0.108 Uiso 1 1 calc R . . O1 O 1.1695(2) 0.3759(2) 0.13750(12) 0.0612(5) Uani 1 1 d D . . H1' H 1.140(4) 0.441(3) 0.1644(17) 0.073 Uiso 1 1 d D . . H2' H 1.079(3) 0.331(4) 0.0949(15) 0.073 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 0.02350(11) 0.02626(10) 0.03544(11) -0.00379(7) -0.00281(7) 0.01005(7) Cl1 0.0322(2) 0.0385(2) 0.0412(2) -0.00947(16) -0.00771(15) 0.01232(16) Cl2 0.0370(2) 0.0361(2) 0.0421(2) 0.00499(15) 0.00774(16) 0.01386(16) N1 0.0255(6) 0.0268(6) 0.0366(6) 0.0017(5) 0.0013(5) 0.0104(5) N2 0.0228(5) 0.0243(5) 0.0326(6) -0.0007(4) -0.0002(4) 0.0081(4) N3 0.0247(6) 0.0263(6) 0.0354(6) -0.0018(5) 0.0011(5) 0.0101(5) N4 0.0427(9) 0.0463(9) 0.0431(8) -0.0106(7) -0.0040(7) 0.0057(7) C1 0.0274(7) 0.0355(8) 0.0422(8) 0.0028(6) -0.0003(6) 0.0121(6) C2 0.0280(8) 0.0425(9) 0.0537(10) 0.0066(7) 0.0011(7) 0.0175(7) C3 0.0359(9) 0.0367(8) 0.0639(11) 0.0034(8) 0.0037(8) 0.0214(7) C4 0.0328(8) 0.0289(7) 0.0544(9) -0.0004(7) 0.0019(7) 0.0153(6) C5 0.0260(6) 0.0265(6) 0.0363(7) 0.0020(5) 0.0025(5) 0.0111(5) C6 0.0245(6) 0.0247(6) 0.0336(7) 0.0014(5) 0.0017(5) 0.0094(5) C7 0.0297(7) 0.0248(6) 0.0359(7) -0.0012(5) 0.0014(6) 0.0099(5) C8 0.0270(7) 0.0255(6) 0.0318(6) 0.0009(5) 0.0009(5) 0.0066(5) C9 0.0245(6) 0.0288(7) 0.0357(7) 0.0003(5) -0.0009(5) 0.0095(5) C10 0.0242(6) 0.0257(6) 0.0326(6) 0.0008(5) 0.0015(5) 0.0095(5) C11 0.0248(6) 0.0258(6) 0.0339(7) 0.0012(5) 0.0027(5) 0.0098(5) C12 0.0277(7) 0.0327(7) 0.0465(8) -0.0005(6) 0.0002(6) 0.0141(6) C13 0.0356(8) 0.0345(8) 0.0543(10) 0.0014(7) 0.0035(7) 0.0201(7) C14 0.0396(9) 0.0298(7) 0.0511(9) -0.0032(7) 0.0048(7) 0.0167(7) C15 0.0323(8) 0.0283(7) 0.0418(8) -0.0041(6) 0.0013(6) 0.0107(6) C16 0.0289(7) 0.0293(7) 0.0319(7) -0.0021(5) 0.0005(5) 0.0074(5) C17 0.0454(10) 0.0292(7) 0.0404(8) 0.0008(6) -0.0017(7) 0.0066(7) C18 0.0508(11) 0.0337(9) 0.0474(10) -0.0059(7) -0.0013(8) 0.0003(8) C19 0.0425(10) 0.0517(11) 0.0387(8) -0.0038(8) -0.0067(7) 0.0165(8) C20 0.0419(9) 0.0364(8) 0.0398(8) -0.0010(7) -0.0052(7) 0.0145(7) O100 0.0725(12) 0.0582(10) 0.0694(11) -0.0072(8) -0.0101(9) 0.0370(9) C200 0.097(2) 0.0539(14) 0.0537(13) 0.0044(11) -0.0035(13) 0.0197(14) O1 0.0482(9) 0.0568(10) 0.0684(10) -0.0226(8) -0.0151(8) 0.0263(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N2 1.9410(15) . ? Cu1 N3 2.0379(14) . ? Cu1 N1 2.0379(14) . ? Cu1 Cl1 2.2246(11) . ? Cu1 Cl2 2.5792(10) . ? N1 C1 1.337(2) . ? N1 C5 1.349(2) . ? N2 C10 1.3344(19) . ? N2 C6 1.3381(19) . ? N3 C15 1.336(2) . ? N3 C11 1.348(2) . ? N4 C18 1.322(3) . ? N4 C19 1.329(3) . ? C1 C2 1.390(2) . ? C1 H1 0.9400 . ? C2 C3 1.378(3) . ? C2 H2 0.9400 . ? C3 C4 1.384(2) . ? C3 H3 0.9400 . ? C4 C5 1.385(2) . ? C4 H4 0.9400 . ? C5 C6 1.477(2) . ? C6 C7 1.385(2) . ? C7 C8 1.399(2) . ? C7 H7 0.9400 . ? C8 C9 1.408(2) . ? C8 C16 1.475(2) . ? C9 C10 1.383(2) . ? C9 H9 0.9400 . ? C10 C11 1.482(2) . ? C11 C12 1.388(2) . ? C12 C13 1.388(2) . ? C12 H12 0.9400 . ? C13 C14 1.371(3) . ? C13 H13 0.9400 . ? C14 C15 1.391(2) . ? C14 H14 0.9400 . ? C15 H15 0.9400 . ? C16 C20 1.387(2) . ? C16 C17 1.387(2) . ? C17 C18 1.391(3) . ? C17 H17 0.9400 . ? C18 H18 0.9400 . ? C19 C20 1.383(3) . ? C19 H19 0.9400 . ? C20 H20 0.9400 . ? O100 C200 1.382(3) . ? O100 H100 0.8300 . ? C200 H20D 0.9700 . ? C200 H20E 0.9700 . ? C200 H20F 0.9700 . ? O1 H1' 0.796(17) . ? O1 H2' 0.877(16) . ? 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 N3 79.68(6) . . ? N2 Cu1 N1 79.66(6) . . ? N3 Cu1 N1 158.44(6) . . ? N2 Cu1 Cl1 167.17(4) . . ? N3 Cu1 Cl1 99.39(5) . . ? N1 Cu1 Cl1 99.37(5) . . ? N2 Cu1 Cl2 89.65(5) . . ? N3 Cu1 Cl2 90.19(5) . . ? N1 Cu1 Cl2 95.79(5) . . ? Cl1 Cu1 Cl2 103.17(3) . . ? C1 N1 C5 118.67(14) . . ? C1 N1 Cu1 126.94(12) . . ? C5 N1 Cu1 114.38(10) . . ? C10 N2 C6 122.52(13) . . ? C10 N2 Cu1 118.62(10) . . ? C6 N2 Cu1 118.65(10) . . ? C15 N3 C11 118.75(14) . . ? C15 N3 Cu1 126.70(11) . . ? C11 N3 Cu1 114.35(10) . . ? C18 N4 C19 117.10(17) . . ? N1 C1 C2 122.63(16) . . ? N1 C1 H1 118.7 . . ? C2 C1 H1 118.7 . . ? C3 C2 C1 118.57(16) . . ? C3 C2 H2 120.7 . . ? C1 C2 H2 120.7 . . ? C2 C3 C4 119.15(16) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C3 C4 C5 119.35(17) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? N1 C5 C4 121.63(15) . . ? N1 C5 C6 113.99(13) . . ? C4 C5 C6 124.37(15) . . ? N2 C6 C7 120.38(14) . . ? N2 C6 C5 113.03(13) . . ? C7 C6 C5 126.59(14) . . ? C6 C7 C8 118.40(14) . . ? C6 C7 H7 120.8 . . ? C8 C7 H7 120.8 . . ? C7 C8 C9 119.88(14) . . ? C7 C8 C16 120.72(14) . . ? C9 C8 C16 119.39(14) . . ? C10 C9 C8 118.11(14) . . ? C10 C9 H9 120.9 . . ? C8 C9 H9 120.9 . . ? N2 C10 C9 120.66(14) . . ? N2 C10 C11 113.09(13) . . ? C9 C10 C11 126.24(14) . . ? N3 C11 C12 121.68(14) . . ? N3 C11 C10 113.84(13) . . ? C12 C11 C10 124.48(14) . . ? C11 C12 C13 118.94(16) . . ? C11 C12 H12 120.5 . . ? C13 C12 H12 120.5 . . ? C14 C13 C12 119.38(16) . . ? C14 C13 H13 120.3 . . ? C12 C13 H13 120.3 . . ? C13 C14 C15 118.68(16) . . ? C13 C14 H14 120.7 . . ? C15 C14 H14 120.7 . . ? N3 C15 C14 122.55(16) . . ? N3 C15 H15 118.7 . . ? C14 C15 H15 118.7 . . ? C20 C16 C17 117.69(16) . . ? C20 C16 C8 120.30(15) . . ? C17 C16 C8 122.01(15) . . ? C16 C17 C18 118.67(18) . . ? C16 C17 H17 120.7 . . ? C18 C17 H17 120.7 . . ? N4 C18 C17 123.84(19) . . ? N4 C18 H18 118.1 . . ? C17 C18 H18 118.1 . . ? N4 C19 C20 123.69(19) . . ? N4 C19 H19 118.2 . . ? C20 C19 H19 118.2 . . ? C19 C20 C16 118.99(18) . . ? C19 C20 H20 120.5 . . ? C16 C20 H20 120.5 . . ? C200 O100 H100 109.5 . . ? O100 C200 H20D 109.5 . . ? O100 C200 H20E 109.5 . . ? H20D C200 H20E 109.5 . . ? O100 C200 H20F 109.5 . . ? H20D C200 H20F 109.5 . . ? H20E C200 H20F 109.5 . . ? H1' O1 H2' 103(3) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.489 _refine_diff_density_min -0.700 _refine_diff_density_rms 0.066 # Attachment 'JB1241.CIF' data_jb1241 _database_code_depnum_ccdc_archive 'CCDC 732264' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H14 Cl2 Cu1 N4, H2 O' _chemical_formula_sum 'C20 H16 Cl2 Cu N4 O' _chemical_formula_weight 462.82 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.6108(9) _cell_length_b 14.2027(13) _cell_length_c 15.6746(14) _cell_angle_alpha 88.347(7) _cell_angle_beta 78.786(8) _cell_angle_gamma 78.373(8) _cell_volume 1841.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.29 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.669 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 940 _exptl_absorpt_coefficient_mu 1.496 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6226 _exptl_absorpt_correction_T_max 0.6709 _exptl_absorpt_process_details '(Blessing 1951)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(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 'Stoe IPDS' _diffrn_measurement_method 'w\ scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 45891 _diffrn_reflns_av_R_equivalents 0.0391 _diffrn_reflns_av_sigmaI/netI 0.0214 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.46 _diffrn_reflns_theta_max 30.00 _reflns_number_total 10578 _reflns_number_gt 10011 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Stoe IPDS' _computing_cell_refinement 'Stoe IPDS' _computing_data_reduction 'Stoe IPDS' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0379P)^2^+0.9055P] 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 10578 _refine_ls_number_parameters 517 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0324 _refine_ls_R_factor_gt 0.0303 _refine_ls_wR_factor_ref 0.0802 _refine_ls_wR_factor_gt 0.0790 _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_restrained_S_all 1.082 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.15719(19) 0.09362(11) 0.96569(10) 0.0276(3) Uani 1 1 d . . . H1 H -0.1964 0.0634 0.9241 0.033 Uiso 1 1 calc R . . C2 C -0.1867(2) 0.06471(11) 1.05121(10) 0.0309(3) Uani 1 1 d . . . H2 H -0.2453 0.0158 1.0676 0.037 Uiso 1 1 calc R . . C3 C -0.1286(2) 0.10887(12) 1.11220(10) 0.0337(3) Uani 1 1 d . . . H3 H -0.1461 0.0898 1.1706 0.040 Uiso 1 1 calc R . . C4 C -0.0442(2) 0.18177(11) 1.08650(9) 0.0304(3) Uani 1 1 d . . . H4 H -0.0039 0.2128 1.1271 0.036 Uiso 1 1 calc R . . C5 C -0.02062(17) 0.20784(10) 1.00004(9) 0.0231(2) Uani 1 1 d . . . C6 C 0.05913(17) 0.28753(10) 0.96445(8) 0.0220(2) Uani 1 1 d . . . C7 C 0.11953(18) 0.34861(10) 1.01106(9) 0.0234(2) Uani 1 1 d . . . H7 H 0.1166 0.3398 1.0710 0.028 Uiso 1 1 calc R . . C8 C 0.18509(16) 0.42377(10) 0.96776(9) 0.0217(2) Uani 1 1 d . . . C9 C 0.18586(18) 0.43419(10) 0.87835(9) 0.0244(2) Uani 1 1 d . . . H9 H 0.2289 0.4837 0.8474 0.029 Uiso 1 1 calc R . . C10 C 0.12223(17) 0.37043(10) 0.83619(8) 0.0224(2) Uani 1 1 d . . . C11 C 0.10596(17) 0.37285(10) 0.74377(8) 0.0225(2) Uani 1 1 d . . . C12 C 0.15503(19) 0.43992(10) 0.68453(9) 0.0271(3) Uani 1 1 d . . . H12 H 0.2032 0.4884 0.7014 0.032 Uiso 1 1 calc R . . C13 C 0.1320(2) 0.43455(11) 0.59968(10) 0.0302(3) Uani 1 1 d . . . H13 H 0.1642 0.4796 0.5583 0.036 Uiso 1 1 calc R . . C14 C 0.0616(2) 0.36255(12) 0.57662(9) 0.0301(3) Uani 1 1 d . . . H14 H 0.0459 0.3574 0.5194 0.036 Uiso 1 1 calc R . . C15 C 0.0143(2) 0.29801(11) 0.63946(9) 0.0293(3) Uani 1 1 d . . . H15 H -0.0342 0.2491 0.6239 0.035 Uiso 1 1 calc R . . C16 C 0.24792(16) 0.49128(10) 1.01639(9) 0.0222(2) Uani 1 1 d . . . C17 C 0.2530(2) 0.48011(12) 1.10440(9) 0.0298(3) Uani 1 1 d . . . H17 H 0.2155 0.4287 1.1351 0.036 Uiso 1 1 calc R . . C18 C 0.3132(2) 0.54483(12) 1.14655(10) 0.0333(3) Uani 1 1 d . . . H18 H 0.3176 0.5379 1.2059 0.040 Uiso 1 1 calc R . . C19 C 0.3668(2) 0.61996(12) 1.09971(10) 0.0316(3) Uani 1 1 d . . . H19 H 0.4079 0.6637 1.1286 0.038 Uiso 1 1 calc R . . C20 C 0.3046(2) 0.56999(11) 0.97584(10) 0.0290(3) Uani 1 1 d . . . H20 H 0.3016 0.5790 0.9165 0.035 Uiso 1 1 calc R . . Cl1 Cl -0.18465(6) 0.13963(3) 0.75752(2) 0.03736(9) Uani 1 1 d . . . Cl2 Cl 0.25055(5) 0.09213(3) 0.77151(2) 0.02883(7) Uani 1 1 d . . . Cu1 Cu -0.01501(2) 0.208170(12) 0.816157(10) 0.02351(5) Uani 1 1 d . . . N1 N -0.07518(15) 0.16287(9) 0.94014(7) 0.0237(2) Uani 1 1 d . . . N2 N 0.06283(15) 0.29917(8) 0.87951(7) 0.0224(2) Uani 1 1 d . . . N3 N 0.03522(16) 0.30277(9) 0.72125(8) 0.0249(2) Uani 1 1 d . . . N4 N 0.36296(19) 0.63329(10) 1.01554(9) 0.0341(3) Uani 1 1 d . . . C33 C 0.5346(2) 0.31370(12) 0.64201(11) 0.0336(3) Uani 1 1 d . . . H33 H 0.5419 0.3173 0.7008 0.040 Uiso 1 1 calc R . . C21 C 0.4735(2) 0.24575(11) 0.15766(10) 0.0291(3) Uani 1 1 d . . . H21 H 0.5160 0.3016 0.1445 0.035 Uiso 1 1 calc R . . C22 C 0.4362(2) 0.19751(12) 0.09098(10) 0.0314(3) Uani 1 1 d . . . H22 H 0.4522 0.2205 0.0337 0.038 Uiso 1 1 calc R . . C23 C 0.3752(2) 0.11526(13) 0.11048(10) 0.0342(3) Uani 1 1 d . . . H23 H 0.3503 0.0809 0.0663 0.041 Uiso 1 1 calc R . . C24 C 0.3508(2) 0.08344(12) 0.19584(10) 0.0321(3) Uani 1 1 d . . . H24 H 0.3090 0.0276 0.2103 0.038 Uiso 1 1 calc R . . C25 C 0.38940(18) 0.13580(10) 0.25906(9) 0.0250(3) Uani 1 1 d . . . C26 C 0.36567(18) 0.11199(10) 0.35235(9) 0.0242(2) Uani 1 1 d . . . C27 C 0.29906(19) 0.03643(10) 0.39125(9) 0.0263(3) Uani 1 1 d . . . H27 H 0.2701 -0.0080 0.3570 0.032 Uiso 1 1 calc R . . C28 C 0.27537(17) 0.02685(10) 0.48170(9) 0.0227(2) Uani 1 1 d . . . C30 C 0.39501(17) 0.16517(10) 0.48655(9) 0.0224(2) Uani 1 1 d . . . C31 C 0.45973(17) 0.23879(10) 0.52609(9) 0.0237(2) Uani 1 1 d . . . C32 C 0.4670(2) 0.24232(11) 0.61361(10) 0.0288(3) Uani 1 1 d . . . H32 H 0.4272 0.1975 0.6527 0.035 Uiso 1 1 calc R . . C34 C 0.5909(2) 0.37934(12) 0.58347(11) 0.0348(3) Uani 1 1 d . . . H34 H 0.6360 0.4285 0.6018 0.042 Uiso 1 1 calc R . . C35 C 0.5795(2) 0.37112(12) 0.49699(11) 0.0317(3) Uani 1 1 d . . . H35 H 0.6179 0.4156 0.4569 0.038 Uiso 1 1 calc R . . C36 C 0.19803(17) -0.05058(10) 0.52529(9) 0.0231(2) Uani 1 1 d . . . C37 C 0.1564(3) -0.05691(14) 0.61505(11) 0.0431(4) Uani 1 1 d . . . H37 H 0.1773 -0.0112 0.6512 0.052 Uiso 1 1 calc R . . C38 C 0.0838(3) -0.13125(16) 0.65073(11) 0.0494(5) Uani 1 1 d . . . H38 H 0.0558 -0.1368 0.7114 0.059 Uiso 1 1 calc R . . C39 C 0.0529(2) -0.19684(12) 0.59674(11) 0.0342(3) Uani 1 1 d . . . H39 H 0.0040 -0.2472 0.6218 0.041 Uiso 1 1 calc R . . C40 C 0.1599(2) -0.12055(11) 0.47711(9) 0.0297(3) Uani 1 1 d . . . H40 H 0.1859 -0.1171 0.4162 0.036 Uiso 1 1 calc R . . N5 N 0.45115(15) 0.21587(9) 0.23962(8) 0.0251(2) Uani 1 1 d . . . N6 N 0.41077(15) 0.17404(8) 0.40040(8) 0.0235(2) Uani 1 1 d . . . N7 N 0.51609(16) 0.30249(9) 0.46858(8) 0.0257(2) Uani 1 1 d . . . N8 N 0.08924(19) -0.19212(10) 0.51092(9) 0.0336(3) Uani 1 1 d . . . Cl3 Cl 0.66816(5) 0.36694(3) 0.27112(3) 0.03928(9) Uani 1 1 d . . . Cl4 Cl 0.23373(5) 0.40632(3) 0.35644(2) 0.03248(8) Uani 1 1 d . . . Cu2 Cu 0.48364(2) 0.285856(12) 0.344269(11) 0.02397(5) Uani 1 1 d . . . C29 C 0.32590(17) 0.09295(10) 0.52981(9) 0.0238(2) Uani 1 1 d . . . H29 H 0.3129 0.0882 0.5906 0.029 Uiso 1 1 calc R . . O1 O 0.05846(18) 0.32316(12) 0.22457(8) 0.0427(3) Uani 1 1 d D . . O2 O 0.4583(3) 0.1740(3) 0.88436(17) 0.1069(11) Uani 1 1 d . . . H102 H 0.094(5) 0.347(3) 0.262(2) 0.128 Uiso 1 1 d D . . H101 H -0.039(2) 0.339(3) 0.242(3) 0.128 Uiso 1 1 d D . . H201 H 0.403(6) 0.153(4) 0.856(3) 0.128 Uiso 1 1 d . . . H202 H 0.546(6) 0.165(4) 0.850(3) 0.128 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0335(7) 0.0273(6) 0.0263(6) 0.0008(5) -0.0074(5) -0.0144(5) C2 0.0368(8) 0.0314(7) 0.0283(7) 0.0047(5) -0.0059(6) -0.0170(6) C3 0.0473(9) 0.0367(8) 0.0217(6) 0.0050(5) -0.0066(6) -0.0199(7) C4 0.0427(8) 0.0328(7) 0.0205(6) 0.0006(5) -0.0082(6) -0.0170(6) C5 0.0280(6) 0.0230(6) 0.0204(6) -0.0010(4) -0.0051(5) -0.0095(5) C6 0.0269(6) 0.0225(6) 0.0189(5) -0.0010(4) -0.0049(5) -0.0096(5) C7 0.0300(6) 0.0250(6) 0.0186(5) -0.0008(4) -0.0067(5) -0.0111(5) C8 0.0245(6) 0.0223(6) 0.0204(5) -0.0027(4) -0.0050(4) -0.0080(5) C9 0.0312(7) 0.0246(6) 0.0210(6) -0.0007(5) -0.0061(5) -0.0126(5) C10 0.0283(6) 0.0224(6) 0.0184(5) -0.0017(4) -0.0053(5) -0.0087(5) C11 0.0271(6) 0.0231(6) 0.0192(5) -0.0023(4) -0.0055(5) -0.0082(5) C12 0.0365(7) 0.0248(6) 0.0232(6) 0.0003(5) -0.0071(5) -0.0124(5) C13 0.0398(8) 0.0301(7) 0.0230(6) 0.0049(5) -0.0071(6) -0.0122(6) C14 0.0392(8) 0.0346(7) 0.0199(6) 0.0017(5) -0.0096(5) -0.0117(6) C15 0.0388(8) 0.0320(7) 0.0221(6) -0.0014(5) -0.0099(5) -0.0148(6) C16 0.0238(6) 0.0235(6) 0.0215(6) -0.0037(4) -0.0053(5) -0.0082(5) C17 0.0396(8) 0.0335(7) 0.0216(6) -0.0013(5) -0.0073(5) -0.0183(6) C18 0.0422(9) 0.0397(8) 0.0235(6) -0.0052(6) -0.0093(6) -0.0173(7) C19 0.0355(8) 0.0330(7) 0.0311(7) -0.0081(6) -0.0086(6) -0.0150(6) C20 0.0388(8) 0.0293(7) 0.0239(6) -0.0002(5) -0.0082(6) -0.0160(6) Cl1 0.0490(2) 0.0488(2) 0.02624(16) 0.00149(15) -0.01337(15) -0.03198(18) Cl2 0.03537(17) 0.02895(16) 0.02348(15) -0.00169(12) -0.00491(12) -0.00994(13) Cu1 0.03252(9) 0.02479(8) 0.01778(8) -0.00105(6) -0.00651(6) -0.01462(7) N1 0.0296(6) 0.0248(5) 0.0196(5) -0.0004(4) -0.0056(4) -0.0115(4) N2 0.0288(6) 0.0227(5) 0.0183(5) -0.0018(4) -0.0053(4) -0.0104(4) N3 0.0338(6) 0.0256(5) 0.0189(5) -0.0008(4) -0.0069(4) -0.0125(5) N4 0.0444(8) 0.0324(6) 0.0324(7) -0.0013(5) -0.0103(6) -0.0205(6) C33 0.0415(8) 0.0350(8) 0.0292(7) -0.0062(6) -0.0135(6) -0.0118(6) C21 0.0342(7) 0.0307(7) 0.0243(6) 0.0036(5) -0.0042(5) -0.0124(6) C22 0.0382(8) 0.0372(8) 0.0203(6) 0.0025(5) -0.0051(5) -0.0120(6) C23 0.0465(9) 0.0392(8) 0.0212(6) -0.0022(6) -0.0078(6) -0.0167(7) C24 0.0474(9) 0.0312(7) 0.0225(6) -0.0001(5) -0.0080(6) -0.0180(6) C25 0.0316(7) 0.0247(6) 0.0205(6) 0.0000(5) -0.0047(5) -0.0104(5) C26 0.0314(7) 0.0234(6) 0.0205(6) -0.0002(4) -0.0068(5) -0.0101(5) C27 0.0377(7) 0.0243(6) 0.0207(6) -0.0005(5) -0.0072(5) -0.0131(5) C28 0.0273(6) 0.0213(6) 0.0212(6) -0.0001(4) -0.0056(5) -0.0076(5) C30 0.0259(6) 0.0218(6) 0.0217(6) -0.0010(4) -0.0076(5) -0.0068(5) C31 0.0260(6) 0.0227(6) 0.0247(6) -0.0023(5) -0.0080(5) -0.0068(5) C32 0.0363(7) 0.0288(7) 0.0246(6) -0.0015(5) -0.0100(6) -0.0098(6) C34 0.0402(8) 0.0328(8) 0.0377(8) -0.0072(6) -0.0140(7) -0.0144(6) C35 0.0363(8) 0.0297(7) 0.0344(8) -0.0016(6) -0.0098(6) -0.0157(6) C36 0.0291(6) 0.0220(6) 0.0203(6) 0.0002(4) -0.0064(5) -0.0086(5) C37 0.0730(13) 0.0463(10) 0.0214(7) -0.0006(6) -0.0093(7) -0.0379(9) C38 0.0841(15) 0.0579(11) 0.0198(7) 0.0056(7) -0.0098(8) -0.0465(11) C39 0.0470(9) 0.0343(8) 0.0278(7) 0.0063(6) -0.0104(6) -0.0212(7) C40 0.0437(8) 0.0291(7) 0.0204(6) 0.0000(5) -0.0066(6) -0.0164(6) N5 0.0300(6) 0.0251(5) 0.0222(5) 0.0000(4) -0.0045(4) -0.0110(4) N6 0.0296(6) 0.0225(5) 0.0214(5) 0.0003(4) -0.0070(4) -0.0101(4) N7 0.0294(6) 0.0255(5) 0.0261(5) -0.0003(4) -0.0095(4) -0.0105(4) N8 0.0487(8) 0.0316(6) 0.0265(6) 0.0006(5) -0.0090(5) -0.0199(6) Cl3 0.0421(2) 0.0486(2) 0.03596(19) 0.00708(16) -0.00797(16) -0.03020(18) Cl4 0.03235(17) 0.03483(18) 0.02963(17) -0.00264(13) -0.00900(13) -0.00190(14) Cu2 0.02903(9) 0.02434(8) 0.02236(8) 0.00133(6) -0.00662(6) -0.01278(6) C29 0.0298(7) 0.0236(6) 0.0203(6) -0.0006(4) -0.0074(5) -0.0080(5) O1 0.0446(7) 0.0602(8) 0.0271(6) -0.0033(5) -0.0030(5) -0.0230(6) O2 0.0585(12) 0.185(3) 0.0822(16) -0.0821(18) -0.0069(11) -0.0320(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 C1 N1 1.3318(18) . ? C1 C2 1.381(2) . ? C1 H1 0.9400 . ? C2 C3 1.380(2) . ? C2 H2 0.9400 . ? C3 C4 1.389(2) . ? C3 H3 0.9400 . ? C4 C5 1.3819(19) . ? C4 H4 0.9400 . ? C5 N1 1.3554(17) . ? C5 C6 1.4804(19) . ? C6 N2 1.3320(17) . ? C6 C7 1.3868(18) . ? C7 C8 1.4039(19) . ? C7 H7 0.9400 . ? C8 C9 1.4038(18) . ? C8 C16 1.4848(18) . ? C9 C10 1.3901(18) . ? C9 H9 0.9400 . ? C10 N2 1.3346(17) . ? C10 C11 1.4810(18) . ? C11 N3 1.3544(17) . ? C11 C12 1.3808(19) . ? C12 C13 1.389(2) . ? C12 H12 0.9400 . ? C13 C14 1.379(2) . ? C13 H13 0.9400 . ? C14 C15 1.385(2) . ? C14 H14 0.9400 . ? C15 N3 1.3342(18) . ? C15 H15 0.9400 . ? C16 C17 1.3922(19) . ? C16 C20 1.397(2) . ? C17 C18 1.382(2) . ? C17 H17 0.9400 . ? C18 C19 1.383(2) . ? C18 H18 0.9400 . ? C19 N4 1.333(2) . ? C19 H19 0.9400 . ? C20 N4 1.3355(19) . ? C20 H20 0.9400 . ? Cl1 Cu1 2.2524(4) . ? Cl2 Cu1 2.5219(5) . ? Cu1 N2 1.9462(11) . ? Cu1 N3 2.0184(12) . ? Cu1 N1 2.0322(12) . ? C33 C34 1.381(3) . ? C33 C32 1.389(2) . ? C33 H33 0.9400 . ? C21 N5 1.3315(18) . ? C21 C22 1.387(2) . ? C21 H21 0.9400 . ? C22 C23 1.378(2) . ? C22 H22 0.9400 . ? C23 C24 1.390(2) . ? C23 H23 0.9400 . ? C24 C25 1.384(2) . ? C24 H24 0.9400 . ? C25 N5 1.3526(18) . ? C25 C26 1.4756(19) . ? C26 N6 1.3360(17) . ? C26 C27 1.3881(19) . ? C27 C28 1.3992(19) . ? C27 H27 0.9400 . ? C28 C29 1.4043(18) . ? C28 C36 1.4815(19) . ? C30 N6 1.3356(17) . ? C30 C29 1.3839(19) . ? C30 C31 1.4814(18) . ? C31 N7 1.3515(19) . ? C31 C32 1.3881(19) . ? C32 H32 0.9400 . ? C34 C35 1.388(2) . ? C34 H34 0.9400 . ? C35 N7 1.3344(18) . ? C35 H35 0.9400 . ? C36 C37 1.388(2) . ? C36 C40 1.3917(19) . ? C37 C38 1.384(2) . ? C37 H37 0.9400 . ? C38 C39 1.374(2) . ? C38 H38 0.9400 . ? C39 N8 1.324(2) . ? C39 H39 0.9400 . ? C40 N8 1.333(2) . ? C40 H40 0.9400 . ? N5 Cu2 2.0351(12) . ? N6 Cu2 1.9484(12) . ? N7 Cu2 2.0482(12) . ? Cl3 Cu2 2.2623(5) . ? Cl4 Cu2 2.4433(5) . ? C29 H29 0.9400 . ? O1 H102 0.819(19) . ? O1 H101 0.817(19) . ? O2 H201 0.81(5) . ? O2 H202 0.82(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 122.27(13) . . ? N1 C1 H1 118.9 . . ? C2 C1 H1 118.9 . . ? C3 C2 C1 118.85(14) . . ? C3 C2 H2 120.6 . . ? C1 C2 H2 120.6 . . ? C2 C3 C4 119.42(14) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C5 C4 C3 118.69(14) . . ? C5 C4 H4 120.7 . . ? C3 C4 H4 120.7 . . ? N1 C5 C4 121.59(13) . . ? N1 C5 C6 113.88(12) . . ? C4 C5 C6 124.50(12) . . ? N2 C6 C7 120.95(12) . . ? N2 C6 C5 112.49(11) . . ? C7 C6 C5 126.51(12) . . ? C6 C7 C8 119.26(12) . . ? C6 C7 H7 120.4 . . ? C8 C7 H7 120.4 . . ? C9 C8 C7 118.17(12) . . ? C9 C8 C16 121.44(12) . . ? C7 C8 C16 120.37(12) . . ? C10 C9 C8 119.24(12) . . ? C10 C9 H9 120.4 . . ? C8 C9 H9 120.4 . . ? N2 C10 C9 120.73(12) . . ? N2 C10 C11 112.40(11) . . ? C9 C10 C11 126.84(12) . . ? N3 C11 C12 121.66(12) . . ? N3 C11 C10 113.78(12) . . ? C12 C11 C10 124.56(12) . . ? C11 C12 C13 118.88(13) . . ? C11 C12 H12 120.6 . . ? C13 C12 H12 120.6 . . ? C14 C13 C12 119.40(14) . . ? C14 C13 H13 120.3 . . ? C12 C13 H13 120.3 . . ? C13 C14 C15 118.70(13) . . ? C13 C14 H14 120.7 . . ? C15 C14 H14 120.7 . . ? N3 C15 C14 122.39(14) . . ? N3 C15 H15 118.8 . . ? C14 C15 H15 118.8 . . ? C17 C16 C20 116.44(12) . . ? C17 C16 C8 122.17(12) . . ? C20 C16 C8 121.40(12) . . ? C18 C17 C16 119.85(14) . . ? C18 C17 H17 120.1 . . ? C16 C17 H17 120.1 . . ? C17 C18 C19 118.71(14) . . ? C17 C18 H18 120.6 . . ? C19 C18 H18 120.6 . . ? N4 C19 C18 123.13(14) . . ? N4 C19 H19 118.4 . . ? C18 C19 H19 118.4 . . ? N4 C20 C16 124.52(14) . . ? N4 C20 H20 117.7 . . ? C16 C20 H20 117.7 . . ? N2 Cu1 N3 79.50(5) . . ? N2 Cu1 N1 79.27(5) . . ? N3 Cu1 N1 156.43(5) . . ? N2 Cu1 Cl1 160.26(4) . . ? N3 Cu1 Cl1 98.88(4) . . ? N1 Cu1 Cl1 97.65(4) . . ? N2 Cu1 Cl2 97.52(4) . . ? N3 Cu1 Cl2 94.35(4) . . ? N1 Cu1 Cl2 98.45(4) . . ? Cl1 Cu1 Cl2 102.223(18) . . ? C1 N1 C5 119.16(12) . . ? C1 N1 Cu1 126.28(10) . . ? C5 N1 Cu1 114.54(9) . . ? C6 N2 C10 121.64(12) . . ? C6 N2 Cu1 119.31(9) . . ? C10 N2 Cu1 119.03(9) . . ? C15 N3 C11 118.98(12) . . ? C15 N3 Cu1 125.95(10) . . ? C11 N3 Cu1 114.92(9) . . ? C19 N4 C20 117.35(14) . . ? C34 C33 C32 119.72(15) . . ? C34 C33 H33 120.1 . . ? C32 C33 H33 120.1 . . ? N5 C21 C22 122.41(14) . . ? N5 C21 H21 118.8 . . ? C22 C21 H21 118.8 . . ? C23 C22 C21 118.57(14) . . ? C23 C22 H22 120.7 . . ? C21 C22 H22 120.7 . . ? C22 C23 C24 119.61(14) . . ? C22 C23 H23 120.2 . . ? C24 C23 H23 120.2 . . ? C25 C24 C23 118.56(14) . . ? C25 C24 H24 120.7 . . ? C23 C24 H24 120.7 . . ? N5 C25 C24 121.75(13) . . ? N5 C25 C26 113.87(12) . . ? C24 C25 C26 124.38(13) . . ? N6 C26 C27 120.49(13) . . ? N6 C26 C25 113.04(12) . . ? C27 C26 C25 126.44(12) . . ? C26 C27 C28 119.58(12) . . ? C26 C27 H27 120.2 . . ? C28 C27 H27 120.2 . . ? C27 C28 C29 118.17(12) . . ? C27 C28 C36 120.73(12) . . ? C29 C28 C36 121.11(12) . . ? N6 C30 C29 121.01(12) . . ? N6 C30 C31 112.45(12) . . ? C29 C30 C31 126.54(12) . . ? N7 C31 C32 121.91(13) . . ? N7 C31 C30 113.90(12) . . ? C32 C31 C30 124.17(13) . . ? C31 C32 C33 118.44(14) . . ? C31 C32 H32 120.8 . . ? C33 C32 H32 120.8 . . ? C33 C34 C35 118.48(14) . . ? C33 C34 H34 120.8 . . ? C35 C34 H34 120.8 . . ? N7 C35 C34 122.50(15) . . ? N7 C35 H35 118.7 . . ? C34 C35 H35 118.7 . . ? C37 C36 C40 116.23(13) . . ? C37 C36 C28 122.81(13) . . ? C40 C36 C28 120.95(12) . . ? C38 C37 C36 119.28(15) . . ? C38 C37 H37 120.4 . . ? C36 C37 H37 120.4 . . ? C39 C38 C37 119.47(16) . . ? C39 C38 H38 120.3 . . ? C37 C38 H38 120.3 . . ? N8 C39 C38 122.74(15) . . ? N8 C39 H39 118.6 . . ? C38 C39 H39 118.6 . . ? N8 C40 C36 124.89(13) . . ? N8 C40 H40 117.6 . . ? C36 C40 H40 117.6 . . ? C21 N5 C25 119.09(13) . . ? C21 N5 Cu2 126.05(10) . . ? C25 N5 Cu2 114.65(9) . . ? C30 N6 C26 121.54(12) . . ? C30 N6 Cu2 119.45(9) . . ? C26 N6 Cu2 118.80(9) . . ? C35 N7 C31 118.94(13) . . ? C35 N7 Cu2 126.36(11) . . ? C31 N7 Cu2 114.63(9) . . ? C39 N8 C40 117.39(13) . . ? N6 Cu2 N5 79.42(5) . . ? N6 Cu2 N7 78.85(5) . . ? N5 Cu2 N7 157.13(5) . . ? N6 Cu2 Cl3 155.01(4) . . ? N5 Cu2 Cl3 96.96(4) . . ? N7 Cu2 Cl3 99.71(4) . . ? N6 Cu2 Cl4 103.15(4) . . ? N5 Cu2 Cl4 95.62(4) . . ? N7 Cu2 Cl4 96.18(4) . . ? Cl3 Cu2 Cl4 101.804(19) . . ? C30 C29 C28 119.16(12) . . ? C30 C29 H29 120.4 . . ? C28 C29 H29 120.4 . . ? H102 O1 H101 102(4) . . ? H201 O2 H202 101(4) . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.391 _refine_diff_density_min -0.436 _refine_diff_density_rms 0.056 # Attachment 'JB1242_new.CIF' data_jb1242 _database_code_depnum_ccdc_archive 'CCDC 732265' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H14 Cl2 Cu1 N4, C H4 O' _chemical_formula_sum 'C21 H18 Cl2 Cu N4 O' _chemical_formula_weight 476.83 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall -P2yn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.3335(15) _cell_length_b 15.501(3) _cell_length_c 15.448(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.173(15) _cell_angle_gamma 90.00 _cell_volume 1995.4(7) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description needle _exptl_crystal_colour green _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.587 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 972 _exptl_absorpt_coefficient_mu 1.383 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5447 _exptl_absorpt_correction_T_max 0.9341 _exptl_absorpt_process_details '(Blessing 1951)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(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 'Stoe IPDS' _diffrn_measurement_method 'w\ scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16422 _diffrn_reflns_av_R_equivalents 0.0667 _diffrn_reflns_av_sigmaI/netI 0.0346 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.63 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3686 _reflns_number_gt 3321 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Stoe IPDS' _computing_cell_refinement 'Stoe IPDS' _computing_data_reduction 'Stoe IPDS' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0611P)^2^+1.0399P] 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 3686 _refine_ls_number_parameters 264 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0430 _refine_ls_R_factor_gt 0.0382 _refine_ls_wR_factor_ref 0.1040 _refine_ls_wR_factor_gt 0.1006 _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 0.62902(3) 0.199926(19) 0.83813(2) 0.03048(13) Uani 1 1 d . . . Cl1 Cl 0.40791(9) 0.27860(6) 0.86250(5) 0.0490(2) Uani 1 1 d . . . Cl2 Cl 0.72491(8) 0.24691(4) 0.69267(4) 0.03546(17) Uani 1 1 d . . . N1 N 0.7876(3) 0.27121(14) 0.90979(15) 0.0324(5) Uani 1 1 d . . . N2 N 0.7988(2) 0.11523(13) 0.85869(13) 0.0272(4) Uani 1 1 d . . . N3 N 0.5242(2) 0.09106(14) 0.79035(15) 0.0317(5) Uani 1 1 d . . . N4 N 1.2971(2) -0.03918(14) 0.94526(15) 0.0327(5) Uani 1 1 d . . . C1 C 0.7635(3) 0.35078(18) 0.93959(19) 0.0390(6) Uani 1 1 d . . . H1 H 0.6682 0.3795 0.9245 0.047 Uiso 1 1 calc R . . C2 C 0.8732(4) 0.39244(19) 0.9916(2) 0.0447(7) Uani 1 1 d . . . H2 H 0.8529 0.4487 1.0116 0.054 Uiso 1 1 calc R . . C3 C 1.0131(4) 0.35055(19) 1.0140(2) 0.0427(7) Uani 1 1 d . . . H3 H 1.0887 0.3775 1.0503 0.051 Uiso 1 1 calc R . . C4 C 1.0411(3) 0.26836(18) 0.98255(19) 0.0362(6) Uani 1 1 d . . . H4 H 1.1369 0.2393 0.9961 0.043 Uiso 1 1 calc R . . C5 C 0.9258(3) 0.22966(16) 0.93083(17) 0.0292(5) Uani 1 1 d . . . C6 C 0.9339(3) 0.13966(16) 0.89957(16) 0.0280(5) Uani 1 1 d . . . C7 C 1.0582(3) 0.08175(16) 0.91187(17) 0.0292(5) Uani 1 1 d . . . H7 H 1.1538 0.0996 0.9388 0.035 Uiso 1 1 calc R . . C8 C 1.0405(3) -0.00359(16) 0.88388(16) 0.0280(5) Uani 1 1 d . . . C9 C 0.8966(3) -0.02736(16) 0.84290(17) 0.0303(5) Uani 1 1 d . . . H9 H 0.8806 -0.0842 0.8236 0.036 Uiso 1 1 calc R . . C10 C 0.7783(3) 0.03458(16) 0.83140(16) 0.0281(5) Uani 1 1 d . . . C11 C 0.6203(3) 0.02079(16) 0.78908(17) 0.0291(5) Uani 1 1 d . . . C12 C 0.5727(3) -0.05632(18) 0.75250(18) 0.0348(6) Uani 1 1 d . . . H12 H 0.6414 -0.1044 0.7526 0.042 Uiso 1 1 calc R . . C13 C 0.4203(3) -0.0612(2) 0.71536(19) 0.0397(6) Uani 1 1 d . . . H13 H 0.3846 -0.1128 0.6898 0.048 Uiso 1 1 calc R . . C14 C 0.3225(3) 0.0105(2) 0.71645(19) 0.0406(7) Uani 1 1 d . . . H14 H 0.2194 0.0082 0.6917 0.049 Uiso 1 1 calc R . . C15 C 0.3776(3) 0.08550(19) 0.75421(19) 0.0372(6) Uani 1 1 d . . . H15 H 0.3105 0.1343 0.7547 0.045 Uiso 1 1 calc R . . C16 C 1.1716(3) -0.06753(16) 0.89791(16) 0.0277(5) Uani 1 1 d . . . C17 C 1.1650(3) -0.15005(17) 0.86419(19) 0.0347(6) Uani 1 1 d . . . H17 H 1.0756 -0.1679 0.8315 0.042 Uiso 1 1 calc R . . C18 C 1.2913(3) -0.20617(17) 0.8789(2) 0.0383(6) Uani 1 1 d . . . H18 H 1.2895 -0.2624 0.8562 0.046 Uiso 1 1 calc R . . C19 C 1.4199(3) -0.17801(18) 0.92767(19) 0.0357(6) Uani 1 1 d . . . H19 H 1.5073 -0.2146 0.9392 0.043 Uiso 1 1 calc R . . C20 C 1.4170(3) -0.09479(18) 0.95901(19) 0.0360(6) Uani 1 1 d . . . H20 H 1.5050 -0.0759 0.9922 0.043 Uiso 1 1 calc R . . O1 O 0.0019(3) 0.11532(16) 0.6662(2) 0.0624(7) Uani 1 1 d . . . H1A H -0.0624 0.1536 0.6805 0.094 Uiso 1 1 calc R . . C100 C -0.0643(5) 0.0660(3) 0.6004(3) 0.0706(11) Uani 1 1 d . . . H10A H -0.1695 0.0457 0.6178 0.106 Uiso 1 1 calc R . . H10B H 0.0047 0.0169 0.5888 0.106 Uiso 1 1 calc R . . H10C H -0.0743 0.1007 0.5485 0.106 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 0.02364(18) 0.03057(19) 0.0372(2) 0.00270(12) -0.00643(13) 0.00530(11) Cl1 0.0332(4) 0.0594(5) 0.0543(5) -0.0049(4) -0.0054(3) 0.0195(3) Cl2 0.0344(3) 0.0333(3) 0.0387(4) 0.0048(3) -0.0029(3) 0.0006(2) N1 0.0302(11) 0.0307(11) 0.0363(12) 0.0006(9) -0.0044(9) 0.0058(9) N2 0.0226(9) 0.0288(10) 0.0304(11) 0.0019(8) -0.0051(8) 0.0000(8) N3 0.0220(10) 0.0345(11) 0.0385(12) 0.0079(9) -0.0057(9) -0.0001(8) N4 0.0263(10) 0.0311(11) 0.0405(13) -0.0019(9) -0.0095(9) 0.0028(8) C1 0.0386(14) 0.0315(13) 0.0468(16) -0.0022(12) -0.0065(12) 0.0082(11) C2 0.0487(17) 0.0320(14) 0.0534(18) -0.0075(13) -0.0038(14) 0.0042(12) C3 0.0436(15) 0.0367(15) 0.0477(17) -0.0061(12) -0.0117(13) -0.0031(12) C4 0.0312(13) 0.0344(14) 0.0431(16) -0.0011(12) -0.0082(11) 0.0015(11) C5 0.0282(12) 0.0279(12) 0.0314(13) 0.0010(10) -0.0034(10) 0.0021(10) C6 0.0238(11) 0.0295(12) 0.0307(13) 0.0021(10) -0.0040(9) 0.0004(9) C7 0.0240(11) 0.0306(12) 0.0331(13) -0.0011(10) -0.0074(10) 0.0019(9) C8 0.0234(11) 0.0296(12) 0.0311(12) 0.0017(10) -0.0040(10) 0.0027(9) C9 0.0256(12) 0.0279(12) 0.0375(14) 0.0000(10) -0.0084(10) 0.0015(9) C10 0.0235(11) 0.0290(12) 0.0318(13) 0.0022(10) -0.0066(10) 0.0010(9) C11 0.0227(11) 0.0325(12) 0.0322(13) 0.0061(10) -0.0064(10) -0.0016(9) C12 0.0289(13) 0.0372(14) 0.0383(14) 0.0018(11) -0.0076(11) -0.0014(10) C13 0.0320(14) 0.0479(16) 0.0391(15) -0.0016(12) -0.0099(12) -0.0086(12) C14 0.0256(13) 0.0529(17) 0.0434(16) 0.0081(13) -0.0112(12) -0.0030(11) C15 0.0225(12) 0.0435(15) 0.0456(16) 0.0094(12) -0.0083(11) 0.0012(10) C16 0.0232(11) 0.0294(12) 0.0305(13) 0.0013(10) -0.0041(10) 0.0014(9) C17 0.0270(12) 0.0317(13) 0.0452(15) -0.0020(11) -0.0073(11) 0.0005(10) C18 0.0357(14) 0.0303(13) 0.0487(17) -0.0048(11) -0.0063(13) 0.0037(10) C19 0.0280(13) 0.0344(13) 0.0448(15) 0.0036(11) -0.0032(11) 0.0084(10) C20 0.0259(12) 0.0374(14) 0.0448(15) -0.0011(11) -0.0102(11) 0.0047(10) O1 0.0444(13) 0.0507(14) 0.0920(19) -0.0057(13) -0.0116(12) 0.0100(10) C100 0.057(2) 0.064(2) 0.091(3) -0.020(2) -0.020(2) 0.0123(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N2 1.955(2) . ? Cu1 N3 2.038(2) . ? Cu1 N1 2.045(2) . ? Cu1 Cl1 2.2424(8) . ? Cu1 Cl2 2.4958(9) . ? N1 C1 1.332(4) . ? N1 C5 1.358(3) . ? N2 C10 1.330(3) . ? N2 C6 1.344(3) . ? N3 C15 1.344(3) . ? N3 C11 1.352(3) . ? N4 C20 1.336(3) . ? N4 C16 1.348(3) . ? C1 C2 1.376(4) . ? C1 H1 0.9400 . ? C2 C3 1.378(4) . ? C2 H2 0.9400 . ? C3 C4 1.384(4) . ? C3 H3 0.9400 . ? C4 C5 1.384(4) . ? C4 H4 0.9400 . ? C5 C6 1.478(3) . ? C6 C7 1.383(3) . ? C7 C8 1.399(4) . ? C7 H7 0.9400 . ? C8 C9 1.404(3) . ? C8 C16 1.491(3) . ? C9 C10 1.387(3) . ? C9 H9 0.9400 . ? C10 C11 1.484(3) . ? C11 C12 1.380(4) . ? C12 C13 1.394(4) . ? C12 H12 0.9400 . ? C13 C14 1.378(4) . ? C13 H13 0.9400 . ? C14 C15 1.379(4) . ? C14 H14 0.9400 . ? C15 H15 0.9400 . ? C16 C17 1.382(4) . ? C17 C18 1.384(4) . ? C17 H17 0.9400 . ? C18 C19 1.378(4) . ? C18 H18 0.9400 . ? C19 C20 1.378(4) . ? C19 H19 0.9400 . ? C20 H20 0.9400 . ? O1 C100 1.386(5) . ? O1 H1A 0.8300 . ? C100 H10A 0.9700 . ? C100 H10B 0.9700 . ? C100 H10C 0.9700 . ? 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 N3 79.17(8) . . ? N2 Cu1 N1 78.98(9) . . ? N3 Cu1 N1 156.79(8) . . ? N2 Cu1 Cl1 158.81(7) . . ? N3 Cu1 Cl1 99.18(7) . . ? N1 Cu1 Cl1 98.35(7) . . ? N2 Cu1 Cl2 96.24(7) . . ? N3 Cu1 Cl2 93.07(7) . . ? N1 Cu1 Cl2 96.98(7) . . ? Cl1 Cu1 Cl2 104.95(3) . . ? C1 N1 C5 119.0(2) . . ? C1 N1 Cu1 126.13(18) . . ? C5 N1 Cu1 114.80(17) . . ? C10 N2 C6 121.3(2) . . ? C10 N2 Cu1 119.18(16) . . ? C6 N2 Cu1 119.47(17) . . ? C15 N3 C11 118.7(2) . . ? C15 N3 Cu1 126.28(19) . . ? C11 N3 Cu1 114.77(16) . . ? C20 N4 C16 117.0(2) . . ? N1 C1 C2 122.4(3) . . ? N1 C1 H1 118.8 . . ? C2 C1 H1 118.8 . . ? C1 C2 C3 119.0(3) . . ? C1 C2 H2 120.5 . . ? C3 C2 H2 120.5 . . ? C2 C3 C4 119.3(3) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C3 C4 C5 119.0(3) . . ? C3 C4 H4 120.5 . . ? C5 C4 H4 120.5 . . ? N1 C5 C4 121.3(2) . . ? N1 C5 C6 114.1(2) . . ? C4 C5 C6 124.4(2) . . ? N2 C6 C7 120.5(2) . . ? N2 C6 C5 112.4(2) . . ? C7 C6 C5 127.1(2) . . ? C6 C7 C8 119.5(2) . . ? C6 C7 H7 120.2 . . ? C8 C7 H7 120.2 . . ? C7 C8 C9 118.5(2) . . ? C7 C8 C16 120.5(2) . . ? C9 C8 C16 121.1(2) . . ? C10 C9 C8 118.8(2) . . ? C10 C9 H9 120.6 . . ? C8 C9 H9 120.6 . . ? N2 C10 C9 121.3(2) . . ? N2 C10 C11 112.8(2) . . ? C9 C10 C11 125.9(2) . . ? N3 C11 C12 122.3(2) . . ? N3 C11 C10 113.7(2) . . ? C12 C11 C10 124.0(2) . . ? C11 C12 C13 118.4(3) . . ? C11 C12 H12 120.8 . . ? C13 C12 H12 120.8 . . ? C14 C13 C12 119.3(3) . . ? C14 C13 H13 120.3 . . ? C12 C13 H13 120.3 . . ? C13 C14 C15 119.3(2) . . ? C13 C14 H14 120.4 . . ? C15 C14 H14 120.4 . . ? N3 C15 C14 122.0(3) . . ? N3 C15 H15 119.0 . . ? C14 C15 H15 119.0 . . ? N4 C16 C17 122.4(2) . . ? N4 C16 C8 115.4(2) . . ? C17 C16 C8 122.2(2) . . ? C16 C17 C18 119.4(2) . . ? C16 C17 H17 120.3 . . ? C18 C17 H17 120.3 . . ? C19 C18 C17 118.7(2) . . ? C19 C18 H18 120.6 . . ? C17 C18 H18 120.6 . . ? C20 C19 C18 118.3(2) . . ? C20 C19 H19 120.9 . . ? C18 C19 H19 120.9 . . ? N4 C20 C19 124.2(2) . . ? N4 C20 H20 117.9 . . ? C19 C20 H20 117.9 . . ? C100 O1 H1A 109.5 . . ? O1 C100 H10A 109.5 . . ? O1 C100 H10B 109.5 . . ? H10A C100 H10B 109.5 . . ? O1 C100 H10C 109.5 . . ? H10A C100 H10C 109.5 . . ? H10B C100 H10C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.359 _refine_diff_density_min -0.655 _refine_diff_density_rms 0.069 # Attachment 'JB666.CIF' data_jb666 _database_code_depnum_ccdc_archive 'CCDC 732266' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C80 H60 Cl8 Cu3 Fe2 N16 O2, 4(H2 O), 2(Cl)' _chemical_formula_sum 'C80 H68 Cl10 Cu3 Fe2 N16 O6' _chemical_formula_weight 2006.35 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' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.894(2) _cell_length_b 13.086(3) _cell_length_c 14.509(3) _cell_angle_alpha 108.38(3) _cell_angle_beta 105.60(3) _cell_angle_gamma 96.33(3) _cell_volume 2016.6(10) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour 'dark blue' _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.652 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1017 _exptl_absorpt_coefficient_mu 1.526 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7301 _exptl_absorpt_correction_T_max 0.9415 _exptl_absorpt_process_details '(Blessing 1951)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Stoe IPDS' _diffrn_measurement_method 'w\ scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 35690 _diffrn_reflns_av_R_equivalents 0.1837 _diffrn_reflns_av_sigmaI/netI 0.0941 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 25.05 _reflns_number_total 7142 _reflns_number_gt 5662 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Stoe IPDS' _computing_cell_refinement 'Stoe IPDS' _computing_data_reduction 'Stoe IPDS' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0935P)^2^+4.4095P] 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 7142 _refine_ls_number_parameters 547 _refine_ls_number_restraints 15 _refine_ls_R_factor_all 0.0985 _refine_ls_R_factor_gt 0.0789 _refine_ls_wR_factor_ref 0.2082 _refine_ls_wR_factor_gt 0.1946 _refine_ls_goodness_of_fit_ref 1.119 _refine_ls_restrained_S_all 1.118 _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 Fe1 Fe -0.34424(8) 0.23214(7) -0.13354(6) 0.0300(2) Uani 1 1 d . . . Cu1 Cu 0.5000 0.5000 0.5000 0.0345(3) Uani 1 2 d S . . Cu2 Cu -1.12933(8) -0.08857(7) -0.81470(7) 0.0450(3) Uani 1 1 d . . . Cl1 Cl -1.2230(2) 0.05006(16) -0.79358(17) 0.0675(6) Uani 1 1 d . . . Cl2 Cl -1.18925(17) -0.26009(15) -0.82282(16) 0.0572(5) Uani 1 1 d . . . Cl3 Cl -1.1156(2) -0.1195(2) -0.97001(17) 0.0757(7) Uani 1 1 d . . . Cl4 Cl 0.53410(15) 0.65073(12) 0.45441(12) 0.0393(4) Uani 1 1 d . . . N1 N -0.4064(4) 0.1999(4) -0.0298(4) 0.0315(11) Uani 1 1 d . . . N2 N -0.2025(4) 0.2843(4) -0.0220(4) 0.0317(11) Uani 1 1 d . . . N3 N -0.2380(5) 0.2879(4) -0.1991(4) 0.0335(11) Uani 1 1 d . . . N4 N 0.3432(5) 0.4397(4) 0.3836(4) 0.0319(11) Uani 1 1 d . . . C1 C -0.5202(6) 0.1563(5) -0.0413(5) 0.0376(14) Uani 1 1 d . . . H1A H -0.5785 0.1339 -0.1072 0.045 Uiso 1 1 calc R . . C2 C -0.5556(6) 0.1430(6) 0.0378(6) 0.0439(16) Uani 1 1 d . . . H2A H -0.6355 0.1088 0.0256 0.053 Uiso 1 1 calc R . . C3 C -0.4728(6) 0.1804(6) 0.1356(6) 0.0445(16) Uani 1 1 d . . . H3A H -0.4962 0.1761 0.1922 0.053 Uiso 1 1 calc R . . C4 C -0.3559(6) 0.2237(5) 0.1492(5) 0.0379(14) Uani 1 1 d . . . H4A H -0.2973 0.2483 0.2151 0.045 Uiso 1 1 calc R . . C5 C -0.3246(5) 0.2311(5) 0.0656(5) 0.0327(13) Uani 1 1 d . . . C6 C -0.2031(5) 0.2738(5) 0.0694(5) 0.0304(12) Uani 1 1 d . . . C7 C -0.0966(6) 0.2993(5) 0.1485(5) 0.0349(13) Uani 1 1 d . . . H7A H -0.0969 0.2909 0.2112 0.042 Uiso 1 1 calc R . . C8 C 0.0103(6) 0.3370(5) 0.1368(5) 0.0369(14) Uani 1 1 d . . . C9 C 0.0078(5) 0.3497(5) 0.0421(5) 0.0313(13) Uani 1 1 d . . . H9A H 0.0795 0.3766 0.0323 0.038 Uiso 1 1 calc R . . C10 C -0.1003(6) 0.3223(5) -0.0349(5) 0.0335(13) Uani 1 1 d . . . C11 C -0.1218(5) 0.3286(5) -0.1383(5) 0.0313(13) Uani 1 1 d . . . C12 C -0.0378(6) 0.3757(5) -0.1706(5) 0.0386(14) Uani 1 1 d . . . H12A H 0.0420 0.4057 -0.1258 0.046 Uiso 1 1 calc R . . C13 C -0.0697(7) 0.3796(6) -0.2687(6) 0.0428(15) Uani 1 1 d . . . H13A H -0.0125 0.4098 -0.2930 0.051 Uiso 1 1 calc R . . C14 C -0.1885(6) 0.3376(5) -0.3299(5) 0.0391(15) Uani 1 1 d . . . H14A H -0.2142 0.3399 -0.3970 0.047 Uiso 1 1 calc R . . C15 C -0.2680(6) 0.2930(5) -0.2932(5) 0.0367(14) Uani 1 1 d . . . H15A H -0.3486 0.2642 -0.3365 0.044 Uiso 1 1 calc R . . C16 C 0.1253(5) 0.3667(5) 0.2204(5) 0.0332(13) Uani 1 1 d . . . C17 C 0.1297(6) 0.3883(5) 0.3225(5) 0.0382(14) Uani 1 1 d . . . H17A H 0.0577 0.3794 0.3384 0.046 Uiso 1 1 calc R . . C18 C 0.2379(6) 0.4223(5) 0.3997(5) 0.0361(14) Uani 1 1 d . . . H18A H 0.2381 0.4341 0.4678 0.043 Uiso 1 1 calc R . . C19 C 0.3391(6) 0.4167(5) 0.2848(5) 0.0372(14) Uani 1 1 d . . . H19A H 0.4125 0.4278 0.2714 0.045 Uiso 1 1 calc R . . C20 C 0.2366(6) 0.3786(5) 0.2038(5) 0.0402(15) Uani 1 1 d . . . H20A H 0.2399 0.3600 0.1360 0.048 Uiso 1 1 calc R . . N5 N -0.4075(4) 0.3683(4) -0.1156(4) 0.0325(11) Uani 1 1 d . . . N6 N -0.4836(5) 0.1775(4) -0.2466(4) 0.0333(11) Uani 1 1 d . . . N7 N -0.3236(5) 0.0794(4) -0.1919(4) 0.0358(12) Uani 1 1 d . . . N8 N -1.0061(5) -0.0276(5) -0.6753(4) 0.0421(13) Uani 1 1 d . . . C21 C -0.3544(6) 0.4698(5) -0.0464(5) 0.0357(14) Uani 1 1 d . . . H21A H -0.2808 0.4791 0.0049 0.043 Uiso 1 1 calc R . . C22 C -0.4025(6) 0.5615(5) -0.0466(5) 0.0388(14) Uani 1 1 d . . . H22A H -0.3620 0.6322 0.0031 0.047 Uiso 1 1 calc R . . C23 C -0.5099(6) 0.5488(5) -0.1200(6) 0.0426(16) Uani 1 1 d . . . H23A H -0.5449 0.6104 -0.1212 0.051 Uiso 1 1 calc R . . C24 C -0.5657(6) 0.4452(5) -0.1917(5) 0.0380(14) Uani 1 1 d . . . H24A H -0.6398 0.4348 -0.2427 0.046 Uiso 1 1 calc R . . C25 C -0.5132(6) 0.3563(5) -0.1893(5) 0.0365(14) Uani 1 1 d . . . C26 C -0.5589(6) 0.2444(5) -0.2634(5) 0.0323(13) Uani 1 1 d . . . C27 C -0.6647(6) 0.2061(5) -0.3456(5) 0.0362(14) Uani 1 1 d . . . H27A H -0.7188 0.2530 -0.3548 0.043 Uiso 1 1 calc R . . C28 C -0.6903(6) 0.0978(5) -0.4141(5) 0.0366(14) Uani 1 1 d . . . C29 C -0.6091(6) 0.0309(5) -0.3962(5) 0.0354(14) Uani 1 1 d . . . H29A H -0.6246 -0.0431 -0.4422 0.043 Uiso 1 1 calc R . . C30 C -0.5070(6) 0.0718(5) -0.3124(5) 0.0345(13) Uani 1 1 d . . . C31 C -0.4123(6) 0.0155(5) -0.2797(5) 0.0372(14) Uani 1 1 d . . . C32 C -0.4102(6) -0.0930(5) -0.3330(5) 0.0392(15) Uani 1 1 d . . . H32A H -0.4724 -0.1363 -0.3948 0.047 Uiso 1 1 calc R . . C33 C -0.3155(7) -0.1363(5) -0.2940(6) 0.0466(17) Uani 1 1 d . . . H33A H -0.3117 -0.2100 -0.3290 0.056 Uiso 1 1 calc R . . C34 C -0.2274(7) -0.0725(6) -0.2048(6) 0.0471(17) Uani 1 1 d . . . H34A H -0.1625 -0.1019 -0.1772 0.057 Uiso 1 1 calc R . . C35 C -0.2329(6) 0.0357(5) -0.1544(5) 0.0382(14) Uani 1 1 d . . . H35A H -0.1713 0.0794 -0.0923 0.046 Uiso 1 1 calc R . . C36 C -0.8007(6) 0.0549(5) -0.5021(5) 0.0393(15) Uani 1 1 d . . . C37 C -0.8550(7) -0.0555(6) -0.5453(6) 0.054(2) Uani 1 1 d . . . H37A H -0.8220 -0.1056 -0.5163 0.065 Uiso 1 1 calc R . . C38 C -0.9555(7) -0.0936(6) -0.6290(6) 0.054(2) Uani 1 1 d . . . H38A H -0.9915 -0.1699 -0.6559 0.064 Uiso 1 1 calc R . . C39 C -0.9564(7) 0.0801(6) -0.6305(6) 0.0464(17) Uani 1 1 d . . . H39A H -0.9934 0.1286 -0.6595 0.056 Uiso 1 1 calc R . . C40 C -0.8557(7) 0.1261(6) -0.5456(6) 0.0476(18) Uani 1 1 d . . . H40A H -0.8243 0.2034 -0.5174 0.057 Uiso 1 1 calc R . . Cl5 Cl 0.16517(18) 0.4883(2) -0.35298(17) 0.0604(5) Uani 1 1 d . . . O2 O -0.2809(5) 0.2101(4) -0.5984(4) 0.0531(13) Uani 1 1 d D . . H2B H -0.212(5) 0.256(6) -0.575(7) 0.064 Uiso 1 1 d D . . H2C H -0.286(8) 0.150(5) -0.649(5) 0.064 Uiso 1 1 d D . . O3 O -0.0687(6) 0.3506(6) -0.5423(6) 0.0710(17) Uani 1 1 d D . . H3B H -0.004(6) 0.334(9) -0.510(8) 0.085 Uiso 1 1 d D . . H3C H -0.033(9) 0.418(4) -0.505(7) 0.085 Uiso 1 1 d D . . O1 O 0.5988(5) 0.3907(4) 0.3774(4) 0.0457(11) Uani 1 1 d D . . H1B H 0.657(6) 0.433(6) 0.373(7) 0.055 Uiso 1 1 d D . . H1C H 0.611(7) 0.329(5) 0.384(7) 0.055 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 Fe1 0.0323(5) 0.0277(4) 0.0222(4) 0.0036(3) 0.0022(3) 0.0082(3) Cu1 0.0341(6) 0.0311(5) 0.0271(6) 0.0082(4) -0.0030(4) 0.0019(4) Cu2 0.0433(5) 0.0425(5) 0.0324(5) 0.0002(4) -0.0005(4) 0.0137(4) Cl1 0.0633(12) 0.0474(10) 0.0602(13) -0.0030(9) -0.0082(10) 0.0243(9) Cl2 0.0471(10) 0.0412(9) 0.0587(12) -0.0001(8) 0.0013(8) 0.0062(8) Cl3 0.0820(15) 0.1019(18) 0.0412(11) 0.0169(11) 0.0179(11) 0.0435(14) Cl4 0.0453(8) 0.0332(7) 0.0313(8) 0.0105(6) 0.0025(6) 0.0052(6) N1 0.032(3) 0.031(2) 0.024(3) 0.004(2) 0.003(2) 0.009(2) N2 0.030(3) 0.032(3) 0.029(3) 0.009(2) 0.004(2) 0.011(2) N3 0.037(3) 0.029(2) 0.027(3) 0.005(2) 0.004(2) 0.010(2) N4 0.035(3) 0.029(2) 0.026(3) 0.007(2) 0.004(2) 0.007(2) C1 0.032(3) 0.035(3) 0.034(3) 0.005(3) 0.001(3) 0.008(3) C2 0.039(4) 0.047(4) 0.046(4) 0.016(3) 0.017(3) 0.001(3) C3 0.042(4) 0.045(4) 0.046(4) 0.019(3) 0.012(3) 0.007(3) C4 0.041(3) 0.036(3) 0.031(3) 0.010(3) 0.007(3) 0.007(3) C5 0.033(3) 0.030(3) 0.031(3) 0.008(2) 0.006(3) 0.010(2) C6 0.034(3) 0.027(3) 0.026(3) 0.006(2) 0.006(2) 0.010(2) C7 0.036(3) 0.034(3) 0.030(3) 0.007(3) 0.007(3) 0.010(3) C8 0.037(3) 0.033(3) 0.031(3) 0.003(3) 0.005(3) 0.012(3) C9 0.029(3) 0.027(3) 0.032(3) 0.007(2) 0.004(2) 0.008(2) C10 0.039(3) 0.029(3) 0.028(3) 0.005(2) 0.009(3) 0.011(3) C11 0.036(3) 0.023(3) 0.030(3) 0.006(2) 0.007(3) 0.008(2) C12 0.045(4) 0.032(3) 0.032(3) 0.004(3) 0.010(3) 0.012(3) C13 0.049(4) 0.043(4) 0.041(4) 0.017(3) 0.018(3) 0.013(3) C14 0.049(4) 0.035(3) 0.030(3) 0.007(3) 0.010(3) 0.015(3) C15 0.046(4) 0.030(3) 0.032(3) 0.008(3) 0.010(3) 0.016(3) C16 0.033(3) 0.028(3) 0.031(3) 0.006(2) 0.005(3) 0.009(2) C17 0.034(3) 0.044(4) 0.031(3) 0.011(3) 0.004(3) 0.008(3) C18 0.043(4) 0.036(3) 0.024(3) 0.007(3) 0.005(3) 0.010(3) C19 0.034(3) 0.043(3) 0.030(3) 0.011(3) 0.006(3) 0.007(3) C20 0.042(4) 0.042(3) 0.027(3) 0.006(3) 0.005(3) 0.008(3) N5 0.031(3) 0.030(2) 0.028(3) 0.003(2) 0.007(2) 0.003(2) N6 0.037(3) 0.032(3) 0.025(3) 0.008(2) 0.004(2) 0.006(2) N7 0.042(3) 0.036(3) 0.027(3) 0.009(2) 0.007(2) 0.015(2) N8 0.037(3) 0.038(3) 0.032(3) 0.000(2) -0.006(2) 0.010(2) C21 0.041(3) 0.035(3) 0.024(3) 0.002(3) 0.007(3) 0.008(3) C22 0.047(4) 0.035(3) 0.027(3) 0.004(3) 0.008(3) 0.008(3) C23 0.045(4) 0.032(3) 0.045(4) 0.007(3) 0.012(3) 0.013(3) C24 0.041(3) 0.036(3) 0.032(3) 0.008(3) 0.007(3) 0.014(3) C25 0.038(3) 0.041(3) 0.025(3) 0.007(3) 0.007(3) 0.012(3) C26 0.036(3) 0.032(3) 0.026(3) 0.006(2) 0.007(3) 0.012(3) C27 0.036(3) 0.035(3) 0.029(3) 0.007(3) 0.003(3) 0.007(3) C28 0.038(3) 0.037(3) 0.025(3) 0.005(3) 0.005(3) 0.004(3) C29 0.049(4) 0.025(3) 0.023(3) 0.004(2) 0.003(3) 0.008(3) C30 0.039(3) 0.027(3) 0.028(3) 0.003(2) 0.004(3) 0.007(3) C31 0.043(3) 0.035(3) 0.028(3) 0.004(3) 0.010(3) 0.012(3) C32 0.048(4) 0.028(3) 0.029(3) 0.003(3) 0.002(3) 0.008(3) C33 0.064(5) 0.028(3) 0.045(4) 0.007(3) 0.017(4) 0.020(3) C34 0.057(4) 0.037(3) 0.042(4) 0.011(3) 0.006(3) 0.022(3) C35 0.043(4) 0.039(3) 0.032(3) 0.010(3) 0.009(3) 0.018(3) C36 0.046(4) 0.038(3) 0.027(3) 0.004(3) 0.007(3) 0.014(3) C37 0.057(5) 0.038(4) 0.046(4) 0.006(3) -0.007(4) 0.017(3) C38 0.060(5) 0.036(4) 0.042(4) 0.004(3) -0.006(4) 0.013(3) C39 0.050(4) 0.039(4) 0.038(4) 0.012(3) -0.001(3) 0.006(3) C40 0.052(4) 0.034(3) 0.038(4) 0.008(3) -0.007(3) 0.002(3) Cl5 0.0458(10) 0.0858(14) 0.0560(12) 0.0355(11) 0.0150(9) 0.0132(10) O2 0.060(3) 0.046(3) 0.050(3) 0.016(2) 0.014(3) 0.014(3) O3 0.062(4) 0.061(4) 0.080(5) 0.024(3) 0.013(3) 0.003(3) O1 0.044(3) 0.039(3) 0.050(3) 0.013(2) 0.012(2) 0.011(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe1 N6 1.867(5) . ? Fe1 N2 1.874(5) . ? Fe1 N5 1.979(5) . ? Fe1 N3 1.979(6) . ? Fe1 N1 1.979(5) . ? Fe1 N7 1.982(5) . ? Cu1 N4 2.023(5) . ? Cu1 N4 2.023(5) 2_666 ? Cu1 Cl4 2.2985(16) 2_666 ? Cu1 Cl4 2.2985(16) . ? Cu2 N8 2.001(5) . ? Cu2 Cl3 2.215(3) . ? Cu2 Cl1 2.215(2) . ? Cu2 Cl2 2.235(2) . ? N1 C1 1.354(8) . ? N1 C5 1.364(8) . ? N2 C10 1.344(8) . ? N2 C6 1.377(8) . ? N3 C15 1.340(8) . ? N3 C11 1.363(8) . ? N4 C18 1.342(9) . ? N4 C19 1.355(8) . ? C1 C2 1.375(10) . ? C1 H1A 0.9500 . ? C2 C3 1.389(10) . ? C2 H2A 0.9500 . ? C3 C4 1.379(10) . ? C3 H3A 0.9500 . ? C4 C5 1.388(9) . ? C4 H4A 0.9500 . ? C5 C6 1.471(9) . ? C6 C7 1.384(9) . ? C7 C8 1.386(9) . ? C7 H7A 0.9500 . ? C8 C9 1.428(9) . ? C8 C16 1.478(9) . ? C9 C10 1.380(9) . ? C9 H9A 0.9500 . ? C10 C11 1.483(9) . ? C11 C12 1.376(9) . ? C12 C13 1.389(10) . ? C12 H12A 0.9500 . ? C13 C14 1.390(10) . ? C13 H13A 0.9500 . ? C14 C15 1.364(10) . ? C14 H14A 0.9500 . ? C15 H15A 0.9500 . ? C16 C17 1.404(9) . ? C16 C20 1.408(10) . ? C17 C18 1.376(9) . ? C17 H17A 0.9500 . ? C18 H18A 0.9500 . ? C19 C20 1.357(9) . ? C19 H19A 0.9500 . ? C20 H20A 0.9500 . ? N5 C21 1.344(8) . ? N5 C25 1.370(8) . ? N6 C26 1.348(8) . ? N6 C30 1.357(8) . ? N7 C35 1.343(8) . ? N7 C31 1.358(8) . ? N8 C39 1.338(9) . ? N8 C38 1.351(10) . ? C21 C22 1.386(9) . ? C21 H21A 0.9500 . ? C22 C23 1.380(10) . ? C22 H22A 0.9500 . ? C23 C24 1.379(9) . ? C23 H23A 0.9500 . ? C24 C25 1.385(9) . ? C24 H24A 0.9500 . ? C25 C26 1.453(9) . ? C26 C27 1.390(9) . ? C27 C28 1.394(9) . ? C27 H27A 0.9500 . ? C28 C29 1.401(9) . ? C28 C36 1.467(9) . ? C29 C30 1.376(9) . ? C29 H29A 0.9500 . ? C30 C31 1.467(9) . ? C31 C32 1.393(9) . ? C32 C33 1.382(10) . ? C32 H32A 0.9500 . ? C33 C34 1.366(10) . ? C33 H33A 0.9500 . ? C34 C35 1.391(9) . ? C34 H34A 0.9500 . ? C35 H35A 0.9500 . ? C36 C37 1.379(10) . ? C36 C40 1.407(10) . ? C37 C38 1.363(10) . ? C37 H37A 0.9500 . ? C38 H38A 0.9500 . ? C39 C40 1.376(10) . ? C39 H39A 0.9500 . ? C40 H40A 0.9500 . ? O2 H2B 0.87(4) . ? O2 H2C 0.87(4) . ? O3 H3B 0.87(4) . ? O3 H3C 0.87(4) . ? O1 H1B 0.87(4) . ? O1 H1C 0.87(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 N6 Fe1 N2 178.5(2) . . ? N6 Fe1 N5 81.0(2) . . ? N2 Fe1 N5 100.3(2) . . ? N6 Fe1 N3 98.2(2) . . ? N2 Fe1 N3 81.1(2) . . ? N5 Fe1 N3 88.4(2) . . ? N6 Fe1 N1 99.6(2) . . ? N2 Fe1 N1 81.2(2) . . ? N5 Fe1 N1 92.2(2) . . ? N3 Fe1 N1 162.2(2) . . ? N6 Fe1 N7 81.1(2) . . ? N2 Fe1 N7 97.6(2) . . ? N5 Fe1 N7 162.0(2) . . ? N3 Fe1 N7 92.0(2) . . ? N1 Fe1 N7 92.9(2) . . ? N4 Cu1 N4 180.000(1) . 2_666 ? N4 Cu1 Cl4 89.79(15) . 2_666 ? N4 Cu1 Cl4 90.21(15) 2_666 2_666 ? N4 Cu1 Cl4 90.21(15) . . ? N4 Cu1 Cl4 89.79(15) 2_666 . ? Cl4 Cu1 Cl4 180.00(3) 2_666 . ? N8 Cu2 Cl3 132.0(2) . . ? N8 Cu2 Cl1 96.61(17) . . ? Cl3 Cu2 Cl1 102.35(11) . . ? N8 Cu2 Cl2 99.70(19) . . ? Cl3 Cu2 Cl2 101.32(11) . . ? Cl1 Cu2 Cl2 129.36(10) . . ? C1 N1 C5 117.0(6) . . ? C1 N1 Fe1 127.8(4) . . ? C5 N1 Fe1 115.0(4) . . ? C10 N2 C6 121.1(5) . . ? C10 N2 Fe1 119.6(4) . . ? C6 N2 Fe1 119.0(4) . . ? C15 N3 C11 117.7(6) . . ? C15 N3 Fe1 127.7(5) . . ? C11 N3 Fe1 114.6(4) . . ? C18 N4 C19 116.4(5) . . ? C18 N4 Cu1 122.3(4) . . ? C19 N4 Cu1 121.3(4) . . ? N1 C1 C2 123.3(6) . . ? N1 C1 H1A 118.4 . . ? C2 C1 H1A 118.4 . . ? C1 C2 C3 119.1(6) . . ? C1 C2 H2A 120.5 . . ? C3 C2 H2A 120.5 . . ? C4 C3 C2 118.8(7) . . ? C4 C3 H3A 120.6 . . ? C2 C3 H3A 120.6 . . ? C3 C4 C5 119.4(6) . . ? C3 C4 H4A 120.3 . . ? C5 C4 H4A 120.3 . . ? N1 C5 C4 122.3(6) . . ? N1 C5 C6 112.9(5) . . ? C4 C5 C6 124.8(6) . . ? N2 C6 C7 119.8(6) . . ? N2 C6 C5 111.4(5) . . ? C7 C6 C5 128.8(6) . . ? C6 C7 C8 120.3(6) . . ? C6 C7 H7A 119.8 . . ? C8 C7 H7A 119.8 . . ? C7 C8 C9 118.6(6) . . ? C7 C8 C16 121.7(6) . . ? C9 C8 C16 119.7(6) . . ? C10 C9 C8 119.0(6) . . ? C10 C9 H9A 120.5 . . ? C8 C9 H9A 120.5 . . ? N2 C10 C9 121.1(6) . . ? N2 C10 C11 111.6(5) . . ? C9 C10 C11 127.3(6) . . ? N3 C11 C12 121.7(6) . . ? N3 C11 C10 112.8(5) . . ? C12 C11 C10 125.4(6) . . ? C11 C12 C13 120.0(6) . . ? C11 C12 H12A 120.0 . . ? C13 C12 H12A 120.0 . . ? C12 C13 C14 117.6(7) . . ? C12 C13 H13A 121.2 . . ? C14 C13 H13A 121.2 . . ? C15 C14 C13 119.7(6) . . ? C15 C14 H14A 120.2 . . ? C13 C14 H14A 120.2 . . ? N3 C15 C14 123.3(6) . . ? N3 C15 H15A 118.4 . . ? C14 C15 H15A 118.4 . . ? C17 C16 C20 115.8(6) . . ? C17 C16 C8 121.4(6) . . ? C20 C16 C8 122.8(6) . . ? C18 C17 C16 120.3(6) . . ? C18 C17 H17A 119.9 . . ? C16 C17 H17A 119.9 . . ? N4 C18 C17 123.3(6) . . ? N4 C18 H18A 118.4 . . ? C17 C18 H18A 118.4 . . ? N4 C19 C20 124.0(6) . . ? N4 C19 H19A 118.0 . . ? C20 C19 H19A 118.0 . . ? C19 C20 C16 120.0(6) . . ? C19 C20 H20A 120.0 . . ? C16 C20 H20A 120.0 . . ? C21 N5 C25 118.0(5) . . ? C21 N5 Fe1 127.6(4) . . ? C25 N5 Fe1 114.1(4) . . ? C26 N6 C30 120.5(5) . . ? C26 N6 Fe1 119.6(4) . . ? C30 N6 Fe1 119.9(4) . . ? C35 N7 C31 119.0(5) . . ? C35 N7 Fe1 127.0(5) . . ? C31 N7 Fe1 114.1(4) . . ? C39 N8 C38 116.2(6) . . ? C39 N8 Cu2 121.2(5) . . ? C38 N8 Cu2 121.9(5) . . ? N5 C21 C22 122.7(6) . . ? N5 C21 H21A 118.7 . . ? C22 C21 H21A 118.7 . . ? C23 C22 C21 119.2(6) . . ? C23 C22 H22A 120.4 . . ? C21 C22 H22A 120.4 . . ? C24 C23 C22 118.9(6) . . ? C24 C23 H23A 120.5 . . ? C22 C23 H23A 120.5 . . ? C23 C24 C25 119.8(6) . . ? C23 C24 H24A 120.1 . . ? C25 C24 H24A 120.1 . . ? N5 C25 C24 121.4(6) . . ? N5 C25 C26 113.2(5) . . ? C24 C25 C26 125.3(6) . . ? N6 C26 C27 121.2(6) . . ? N6 C26 C25 112.0(5) . . ? C27 C26 C25 126.7(6) . . ? C26 C27 C28 119.1(6) . . ? C26 C27 H27A 120.4 . . ? C28 C27 H27A 120.4 . . ? C27 C28 C29 118.5(6) . . ? C27 C28 C36 120.6(6) . . ? C29 C28 C36 120.9(6) . . ? C30 C29 C28 120.2(5) . . ? C30 C29 H29A 119.9 . . ? C28 C29 H29A 119.9 . . ? N6 C30 C29 120.4(6) . . ? N6 C30 C31 110.9(5) . . ? C29 C30 C31 128.7(6) . . ? N7 C31 C32 121.8(6) . . ? N7 C31 C30 114.0(5) . . ? C32 C31 C30 124.2(6) . . ? C33 C32 C31 118.5(6) . . ? C33 C32 H32A 120.7 . . ? C31 C32 H32A 120.7 . . ? C34 C33 C32 119.5(6) . . ? C34 C33 H33A 120.2 . . ? C32 C33 H33A 120.2 . . ? C33 C34 C35 120.0(6) . . ? C33 C34 H34A 120.0 . . ? C35 C34 H34A 120.0 . . ? N7 C35 C34 121.2(6) . . ? N7 C35 H35A 119.4 . . ? C34 C35 H35A 119.4 . . ? C37 C36 C40 117.3(6) . . ? C37 C36 C28 122.1(6) . . ? C40 C36 C28 120.6(6) . . ? C38 C37 C36 120.8(7) . . ? C38 C37 H37A 119.6 . . ? C36 C37 H37A 119.6 . . ? N8 C38 C37 122.8(7) . . ? N8 C38 H38A 118.6 . . ? C37 C38 H38A 118.6 . . ? N8 C39 C40 125.0(7) . . ? N8 C39 H39A 117.5 . . ? C40 C39 H39A 117.5 . . ? C39 C40 C36 117.8(6) . . ? C39 C40 H40A 121.1 . . ? C36 C40 H40A 121.1 . . ? H2B O2 H2C 114(9) . . ? H3B O3 H3C 85(10) . . ? H1B O1 H1C 118(8) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.704 _refine_diff_density_min -1.017 _refine_diff_density_rms 0.127 # Attachment 'JB667.CIF' data_jb667r _database_code_depnum_ccdc_archive 'CCDC 732267' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H15 Cl2 Cu N4, 4(H2 O), Cl' _chemical_formula_sum 'C20 H23 Cl3 Cu N4 O4' _chemical_formula_weight 553.32 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 Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.7958(16) _cell_length_b 11.045(2) _cell_length_c 13.785(3) _cell_angle_alpha 88.48(3) _cell_angle_beta 85.04(3) _cell_angle_gamma 88.29(3) _cell_volume 1181.7(4) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour green _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.549 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 562 _exptl_absorpt_coefficient_mu 1.297 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5356 _exptl_absorpt_correction_T_max 0.9745 _exptl_absorpt_process_details '(Blessing 1951)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(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 'Stoe IPDS' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22384 _diffrn_reflns_av_R_equivalents 0.1587 _diffrn_reflns_av_sigmaI/netI 0.0766 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 25.04 _reflns_number_total 4185 _reflns_number_gt 3804 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Stoe IPDS' _computing_cell_refinement 'Stoe IPDS' _computing_data_reduction 'Stoe IPDS' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1056P)^2^+1.4327P] 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 4185 _refine_ls_number_parameters 310 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.0693 _refine_ls_R_factor_gt 0.0647 _refine_ls_wR_factor_ref 0.1775 _refine_ls_wR_factor_gt 0.1722 _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_restrained_S_all 1.088 _refine_ls_shift/su_max 0.016 _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 0.42093(5) 0.83648(4) 0.03939(3) 0.0276(2) Uani 1 1 d . . . Cl1 Cl 0.22590(13) 0.96318(10) 0.11053(9) 0.0391(3) Uani 1 1 d . . . N1 N 0.5897(4) 0.8241(3) 0.1456(3) 0.0295(7) Uani 1 1 d . . . C1 C 0.5585(5) 0.8545(4) 0.2378(3) 0.0351(9) Uani 1 1 d . . . H1A H 0.4497 0.8880 0.2586 0.042 Uiso 1 1 calc R . . Cl2 Cl 0.29677(12) 0.62854(9) 0.08849(7) 0.0316(3) Uani 1 1 d . . . N2 N 0.6236(4) 0.7690(3) -0.0341(2) 0.0260(7) Uani 1 1 d . . . C2 C 0.6809(6) 0.8386(4) 0.3051(3) 0.0375(10) Uani 1 1 d . . . H2A H 0.6539 0.8593 0.3704 0.045 Uiso 1 1 calc R . . N3 N 0.3440(4) 0.8471(3) -0.0988(2) 0.0273(7) Uani 1 1 d . . . C3 C 0.8421(6) 0.7920(4) 0.2748(3) 0.0376(10) Uani 1 1 d . . . H3A H 0.9277 0.7828 0.3186 0.045 Uiso 1 1 calc R . . N4 N 1.3352(4) 0.4879(4) -0.2878(3) 0.0347(8) Uani 1 1 d D . . H4 H 1.433(4) 0.465(5) -0.322(3) 0.042 Uiso 1 1 d D . . C4 C 0.8758(5) 0.7590(4) 0.1785(3) 0.0327(9) Uani 1 1 d . . . H4A H 0.9847 0.7268 0.1562 0.039 Uiso 1 1 calc R . . C5 C 0.7469(5) 0.7742(4) 0.1153(3) 0.0276(8) Uani 1 1 d . . . C6 C 0.7627(5) 0.7395(4) 0.0125(3) 0.0266(8) Uani 1 1 d . . . C7 C 0.9051(5) 0.6814(4) -0.0365(3) 0.0278(8) Uani 1 1 d . . . H7A H 1.0026 0.6597 -0.0036 0.033 Uiso 1 1 calc R . . C8 C 0.9010(5) 0.6561(4) -0.1344(3) 0.0255(8) Uani 1 1 d . . . C9 C 0.7560(5) 0.6927(4) -0.1824(3) 0.0269(8) Uani 1 1 d . . . H9A H 0.7513 0.6782 -0.2490 0.032 Uiso 1 1 calc R . . C10 C 0.6190(5) 0.7511(4) -0.1292(3) 0.0263(8) Uani 1 1 d . . . C11 C 0.4583(5) 0.7997(4) -0.1681(3) 0.0267(8) Uani 1 1 d . . . C12 C 0.4264(5) 0.7988(4) -0.2649(3) 0.0336(9) Uani 1 1 d . . . H12A H 0.5098 0.7672 -0.3116 0.040 Uiso 1 1 calc R . . C13 C 0.2695(5) 0.8452(5) -0.2930(3) 0.0384(10) Uani 1 1 d . . . H13A H 0.2434 0.8435 -0.3583 0.046 Uiso 1 1 calc R . . C14 C 0.1531(5) 0.8941(4) -0.2219(3) 0.0363(10) Uani 1 1 d . . . H14A H 0.0468 0.9271 -0.2387 0.044 Uiso 1 1 calc R . . C15 C 0.1935(5) 0.8940(4) -0.1269(3) 0.0325(9) Uani 1 1 d . . . H15A H 0.1134 0.9279 -0.0796 0.039 Uiso 1 1 calc R . . C16 C 1.0495(5) 0.5923(4) -0.1886(3) 0.0275(8) Uani 1 1 d . . . C17 C 1.0504(6) 0.5672(5) -0.2860(3) 0.0388(10) Uani 1 1 d . . . H17A H 0.9521 0.5859 -0.3191 0.047 Uiso 1 1 calc R . . C18 C 1.1944(6) 0.5150(5) -0.3352(3) 0.0418(11) Uani 1 1 d . . . H18A H 1.1943 0.4983 -0.4017 0.050 Uiso 1 1 calc R . . C19 C 1.3369(5) 0.5067(4) -0.1930(3) 0.0327(9) Uani 1 1 d . . . H19A H 1.4353 0.4843 -0.1612 0.039 Uiso 1 1 calc R . . C20 C 1.1954(5) 0.5588(4) -0.1408(3) 0.0307(9) Uani 1 1 d . . . H20A H 1.1973 0.5717 -0.0738 0.037 Uiso 1 1 calc R . . O4 O 1.4712(6) 0.3789(5) -0.4907(4) 0.0717(12) Uani 1 1 d D . . H4B H 1.558(7) 0.325(5) -0.488(6) 0.086 Uiso 1 1 d D . . H4C H 1.510(10) 0.416(7) -0.546(3) 0.086 Uiso 1 1 d D . . Cl3 Cl 0.1680(3) 0.7460(2) -0.53521(15) 0.0785(7) Uani 0.67 1 d P . . Cl4 Cl 0.8194(4) 0.7489(3) -0.4427(2) 0.0842(10) Uani 0.33 1 d P . . O6 O 0.1680(3) 0.7460(2) -0.53521(15) 0.0785(7) Uani 0.33 1 d P . . O7 O 0.8194(4) 0.7489(3) -0.4427(2) 0.0842(10) Uani 0.67 1 d P . . O5 O 0.3527(9) 0.9979(6) -0.5534(5) 0.1022(19) Uani 1 1 d D . . H5B H 0.315(10) 1.076(3) -0.557(7) 0.123 Uiso 1 1 d D . . H5C H 0.267(8) 0.947(6) -0.563(7) 0.123 Uiso 1 1 d D . . O3 O 1.6747(4) 0.4252(4) -0.3103(3) 0.0535(10) Uani 1 1 d D . . H3B H 1.690(8) 0.404(6) -0.248(2) 0.064 Uiso 1 1 d D . . H3C H 1.711(8) 0.369(5) -0.353(4) 0.064 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 0.0155(3) 0.0326(3) 0.0347(3) -0.0027(2) -0.00208(19) 0.00317(19) Cl1 0.0258(5) 0.0382(6) 0.0524(7) -0.0074(5) 0.0002(4) 0.0089(4) N1 0.0166(15) 0.0358(19) 0.0360(18) -0.0025(14) -0.0017(13) -0.0005(13) C1 0.0227(19) 0.042(2) 0.040(2) -0.0094(18) 0.0014(17) 0.0009(17) Cl2 0.0228(5) 0.0347(5) 0.0380(5) 0.0023(4) -0.0085(4) -0.0008(4) N2 0.0197(15) 0.0276(17) 0.0310(17) 0.0014(13) -0.0040(12) -0.0010(13) C2 0.033(2) 0.045(3) 0.034(2) -0.0070(19) -0.0008(18) 0.0014(19) N3 0.0160(15) 0.0304(17) 0.0354(17) 0.0012(14) -0.0033(13) 0.0009(13) C3 0.032(2) 0.044(3) 0.039(2) -0.0040(19) -0.0102(18) -0.0009(18) N4 0.0222(17) 0.039(2) 0.042(2) 0.0004(16) 0.0017(14) 0.0049(15) C4 0.0234(19) 0.038(2) 0.038(2) -0.0016(18) -0.0075(16) -0.0016(16) C5 0.0194(18) 0.029(2) 0.034(2) -0.0004(16) -0.0006(15) -0.0045(15) C6 0.0183(17) 0.027(2) 0.034(2) 0.0007(16) -0.0026(15) 0.0002(14) C7 0.0142(17) 0.034(2) 0.036(2) 0.0008(17) -0.0028(15) 0.0022(15) C8 0.0165(17) 0.0278(19) 0.0317(19) 0.0034(15) -0.0005(15) 0.0000(15) C9 0.0185(18) 0.032(2) 0.0300(19) 0.0010(16) -0.0039(15) 0.0003(15) C10 0.0172(17) 0.028(2) 0.034(2) 0.0034(15) -0.0024(15) -0.0005(14) C11 0.0177(18) 0.030(2) 0.032(2) 0.0011(16) -0.0016(15) 0.0006(15) C12 0.0213(19) 0.041(2) 0.038(2) 0.0009(18) -0.0010(16) 0.0025(17) C13 0.027(2) 0.050(3) 0.040(2) 0.006(2) -0.0090(18) 0.0013(19) C14 0.0225(19) 0.040(2) 0.047(2) 0.0088(19) -0.0106(18) 0.0061(17) C15 0.0184(18) 0.034(2) 0.045(2) 0.0045(18) -0.0026(16) 0.0054(16) C16 0.0177(18) 0.029(2) 0.036(2) 0.0011(16) -0.0038(15) 0.0030(15) C17 0.025(2) 0.056(3) 0.035(2) -0.004(2) -0.0056(17) 0.0107(19) C18 0.035(2) 0.054(3) 0.035(2) -0.001(2) -0.0008(18) 0.010(2) C19 0.0172(18) 0.035(2) 0.046(2) -0.0001(18) -0.0040(16) 0.0049(16) C20 0.0197(18) 0.036(2) 0.036(2) -0.0030(17) -0.0041(15) 0.0052(16) O4 0.043(2) 0.081(3) 0.091(3) 0.013(3) -0.013(2) 0.010(2) Cl3 0.0715(13) 0.1056(18) 0.0600(11) -0.0244(11) -0.0226(10) 0.0375(12) Cl4 0.085(2) 0.090(2) 0.084(2) 0.0206(17) -0.0460(17) -0.0097(17) O6 0.0715(13) 0.1056(18) 0.0600(11) -0.0244(11) -0.0226(10) 0.0375(12) O7 0.085(2) 0.090(2) 0.084(2) 0.0206(17) -0.0460(17) -0.0097(17) O5 0.114(5) 0.072(4) 0.115(5) -0.004(3) 0.018(4) 0.006(3) O3 0.0322(18) 0.089(3) 0.0392(18) -0.0027(18) -0.0045(14) 0.0130(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N2 1.942(3) . ? Cu1 N3 2.046(3) . ? Cu1 N1 2.051(3) . ? Cu1 Cl1 2.2180(13) . ? Cu1 Cl2 2.5704(13) . ? N1 C1 1.323(6) . ? N1 C5 1.365(5) . ? C1 C2 1.391(6) . ? C1 H1A 0.9400 . ? N2 C6 1.335(5) . ? N2 C10 1.335(5) . ? C2 C3 1.379(6) . ? C2 H2A 0.9400 . ? N3 C15 1.352(5) . ? N3 C11 1.353(5) . ? C3 C4 1.387(6) . ? C3 H3A 0.9400 . ? N4 C19 1.329(6) . ? N4 C18 1.347(6) . ? N4 H4 0.90(2) . ? C4 C5 1.389(6) . ? C4 H4A 0.9400 . ? C5 C6 1.471(6) . ? C6 C7 1.397(5) . ? C7 C8 1.390(6) . ? C7 H7A 0.9400 . ? C8 C9 1.402(5) . ? C8 C16 1.492(5) . ? C9 C10 1.394(6) . ? C9 H9A 0.9400 . ? C10 C11 1.485(5) . ? C11 C12 1.379(6) . ? C12 C13 1.394(6) . ? C12 H12A 0.9400 . ? C13 C14 1.386(7) . ? C13 H13A 0.9400 . ? C14 C15 1.374(6) . ? C14 H14A 0.9400 . ? C15 H15A 0.9400 . ? C16 C17 1.377(6) . ? C16 C20 1.398(5) . ? C17 C18 1.380(6) . ? C17 H17A 0.9400 . ? C18 H18A 0.9400 . ? C19 C20 1.384(6) . ? C19 H19A 0.9400 . ? C20 H20A 0.9400 . ? O4 H4B 0.89(2) . ? O4 H4C 0.89(2) . ? O5 H5B 0.91(2) . ? O5 H5C 0.90(2) . ? O3 H3B 0.90(2) . ? O3 H3C 0.89(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Cu1 N3 79.25(13) . . ? N2 Cu1 N1 79.56(14) . . ? N3 Cu1 N1 157.26(14) . . ? N2 Cu1 Cl1 163.45(11) . . ? N3 Cu1 Cl1 98.77(10) . . ? N1 Cu1 Cl1 99.17(10) . . ? N2 Cu1 Cl2 94.18(10) . . ? N3 Cu1 Cl2 97.63(10) . . ? N1 Cu1 Cl2 92.07(11) . . ? Cl1 Cu1 Cl2 102.36(5) . . ? C1 N1 C5 119.0(4) . . ? C1 N1 Cu1 127.0(3) . . ? C5 N1 Cu1 113.9(3) . . ? N1 C1 C2 122.4(4) . . ? N1 C1 H1A 118.8 . . ? C2 C1 H1A 118.8 . . ? C6 N2 C10 121.9(3) . . ? C6 N2 Cu1 118.9(3) . . ? C10 N2 Cu1 119.2(3) . . ? C3 C2 C1 119.2(4) . . ? C3 C2 H2A 120.4 . . ? C1 C2 H2A 120.4 . . ? C15 N3 C11 117.9(4) . . ? C15 N3 Cu1 127.3(3) . . ? C11 N3 Cu1 114.8(3) . . ? C2 C3 C4 118.9(4) . . ? C2 C3 H3A 120.6 . . ? C4 C3 H3A 120.6 . . ? C19 N4 C18 121.3(4) . . ? C19 N4 H4 119(3) . . ? C18 N4 H4 119(3) . . ? C3 C4 C5 119.2(4) . . ? C3 C4 H4A 120.4 . . ? C5 C4 H4A 120.4 . . ? N1 C5 C4 121.2(4) . . ? N1 C5 C6 113.7(3) . . ? C4 C5 C6 125.1(4) . . ? N2 C6 C7 120.3(4) . . ? N2 C6 C5 113.6(3) . . ? C7 C6 C5 126.1(4) . . ? C8 C7 C6 119.2(4) . . ? C8 C7 H7A 120.4 . . ? C6 C7 H7A 120.4 . . ? C7 C8 C9 119.2(4) . . ? C7 C8 C16 120.7(3) . . ? C9 C8 C16 120.2(4) . . ? C10 C9 C8 118.6(4) . . ? C10 C9 H9A 120.7 . . ? C8 C9 H9A 120.7 . . ? N2 C10 C9 120.8(4) . . ? N2 C10 C11 113.1(3) . . ? C9 C10 C11 126.2(4) . . ? N3 C11 C12 122.4(4) . . ? N3 C11 C10 113.3(3) . . ? C12 C11 C10 124.3(4) . . ? C11 C12 C13 119.4(4) . . ? C11 C12 H12A 120.3 . . ? C13 C12 H12A 120.3 . . ? C14 C13 C12 118.1(4) . . ? C14 C13 H13A 121.0 . . ? C12 C13 H13A 121.0 . . ? C15 C14 C13 119.8(4) . . ? C15 C14 H14A 120.1 . . ? C13 C14 H14A 120.1 . . ? N3 C15 C14 122.5(4) . . ? N3 C15 H15A 118.8 . . ? C14 C15 H15A 118.8 . . ? C17 C16 C20 118.1(4) . . ? C17 C16 C8 122.1(4) . . ? C20 C16 C8 119.8(4) . . ? C16 C17 C18 120.4(4) . . ? C16 C17 H17A 119.8 . . ? C18 C17 H17A 119.8 . . ? N4 C18 C17 119.9(4) . . ? N4 C18 H18A 120.0 . . ? C17 C18 H18A 120.0 . . ? N4 C19 C20 120.7(4) . . ? N4 C19 H19A 119.6 . . ? C20 C19 H19A 119.6 . . ? C19 C20 C16 119.4(4) . . ? C19 C20 H20A 120.3 . . ? C16 C20 H20A 120.3 . . ? H4B O4 H4C 97(7) . . ? H5B O5 H5C 111(3) . . ? H3B O3 H3C 114(6) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.04 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.031 _refine_diff_density_min -1.070 _refine_diff_density_rms 0.125 # Attachment 'jb1029.cif' data_jb1029_123k _database_code_depnum_ccdc_archive 'CCDC 732268' _audit_creation_date 08-12-16 _audit_creation_method CRYSTALS_ver_12.86 _oxford_structure_analysis_title 'jb1029_123k_0ma in P2(1)/c' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 25.187(4) _cell_length_b 10.8273(17) _cell_length_c 21.822(3) _cell_angle_alpha 90 _cell_angle_beta 93.360(10) _cell_angle_gamma 90 _cell_volume 5940.8(15) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c ' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x,y+1/2,-z+1/2 x,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Cu 0.3201 1.2651 13.3380 3.5828 7.1676 0.2470 5.6158 11.3966 1.6735 64.8126 1.1910 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 12 # Given Formula = C20 H14 Cu1 N7 O3 # Dc = 1.56 Fooo = 3156.00 Mu = 11.42 M = 1391.77 # Found Formula = C20 H16 Cu1 N6 O7 # Dc = 1.73 FOOO = 3156.00 Mu = 11.65 M = 1547.79 _chemical_formula_sum 'C20 H16 Cu1 N6 O7' _chemical_formula_moiety 'C20 H14 Cu N6 O6, H2 O' _chemical_compound_source ? _chemical_formula_weight 515.93 _cell_measurement_reflns_used 2787 _cell_measurement_theta_min 4 _cell_measurement_theta_max 25 _cell_measurement_temperature 123 _exptl_crystal_description needle _exptl_crystal_colour green _exptl_crystal_size_min 0.06 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_max 0.35 _exptl_crystal_density_diffrn 1.730 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 3156 _exptl_absorpt_coefficient_mu 1.165 # Sheldrick geometric approximatio 0.75 0.93 # No experimental values of Tmin/max available _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.75 _exptl_absorpt_correction_T_max 0.93 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device 'Nonius KappaCCD' _diffrn_measurement_device_type Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 1997-2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 123 _diffrn_reflns_number 112956 _reflns_number_total 12277 _diffrn_reflns_av_R_equivalents 0.072 # Number of reflections with Friedels Law is 12277 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 12703 _diffrn_reflns_theta_min 1.870 _diffrn_reflns_theta_max 26.566 _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 26.035 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _reflns_limit_h_min -31 _reflns_limit_h_max 31 _reflns_limit_k_min 0 _reflns_limit_k_max 13 _reflns_limit_l_min 0 _reflns_limit_l_max 27 _oxford_diffrn_Wilson_B_factor 0.99 _oxford_diffrn_Wilson_scale 1111.46 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.87 _refine_diff_density_max 1.00 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>2.0\s(I) _refine_ls_number_reflns 8800 _refine_ls_number_restraints 1062 _refine_ls_number_parameters 920 _oxford_refine_ls_R_factor_ref 0.0760 _refine_ls_wR_factor_ref 0.0819 _refine_ls_goodness_of_fit_ref 1.0047 _refine_ls_shift/su_max 0.002200 # The values computed from all data _oxford_reflns_number_all 12194 _refine_ls_R_factor_all 0.0987 _refine_ls_wR_factor_all 0.1381 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 8800 _refine_ls_R_factor_gt 0.0760 _refine_ls_wR_factor_gt 0.0819 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.311 0.266 0.698E-01 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens Cu1 Cu 0.07915(3) 0.28340(7) 0.34197(3) 0.0108 1.0000 Uani . U . . . . . Cu2 Cu 0.41757(3) 0.25404(8) 0.39811(3) 0.0128 1.0000 Uani . U . . . . . Cu3 Cu 0.75311(3) 0.26987(8) 0.38055(4) 0.0129 1.0000 Uani . U . . . . . N1 N 0.0075(2) 0.3637(5) 0.3579(2) 0.0133 1.0000 Uani . U . . . . . N2 N 0.0771(2) 0.2571(5) 0.4282(2) 0.0111 1.0000 Uani . U . . . . . N3 N 0.1499(2) 0.1938(5) 0.3581(2) 0.0113 1.0000 Uani . U . . . . . N4 N 0.0773(2) 0.1980(5) 0.7522(2) 0.0108 1.0000 Uani . U . . . . . N5 N 0.1082(2) 0.5392(5) 0.4100(2) 0.0141 1.0000 Uani . U . . . . . N6 N 0.0567(2) -0.0142(5) 0.3578(3) 0.0156 1.0000 Uani . U . . . . . N7 N 0.3423(2) 0.3168(5) 0.4109(2) 0.0133 1.0000 Uani . U . . . . . N8 N 0.4168(2) 0.2380(5) 0.4860(2) 0.0124 1.0000 Uani . U . . . . . N9 N 0.4929(2) 0.1867(5) 0.4177(2) 0.0145 1.0000 Uani . U . . . . . N10 N 0.4181(2) 0.2312(6) 0.8074(2) 0.0182 1.0000 Uani . U . . . . . N11 N 0.4453(2) 0.5553(6) 0.3836(3) 0.0199 1.0000 Uani . U . . . . . N12 N 0.3891(2) -0.0277(6) 0.3474(3) 0.0194 1.0000 Uani . U . . . . . N13 N 0.6795(2) 0.3403(6) 0.3914(2) 0.0142 1.0000 Uani . U . . . . . N14 N 0.7536(2) 0.2684(5) 0.4688(2) 0.0119 1.0000 Uani . U . . . . . N15 N 0.8286(2) 0.2026(6) 0.4008(2) 0.0156 1.0000 Uani . U . . . . . N16 N 0.7519(2) 0.2361(6) 0.7907(2) 0.0156 1.0000 Uani . U . . . . . N17 N 0.7745(2) 0.5708(5) 0.3539(3) 0.0181 1.0000 Uani . U . . . . . N18 N 0.7313(2) -0.0168(6) 0.4157(3) 0.0172 1.0000 Uani . U . . . . . C1 C -0.0267(3) 0.4189(6) 0.3177(3) 0.0148 1.0000 Uani . U . . . . . C2 C -0.0746(3) 0.4672(6) 0.3345(3) 0.0158 1.0000 Uani . U . . . . . C3 C -0.0872(3) 0.4635(6) 0.3958(3) 0.0166 1.0000 Uani . U . . . . . C4 C -0.0512(3) 0.4086(6) 0.4380(3) 0.0145 1.0000 Uani . U . . . . . C5 C -0.0043(3) 0.3581(6) 0.4181(3) 0.0125 1.0000 Uani . U . . . . . C6 C 0.0353(2) 0.2958(6) 0.4591(3) 0.0113 1.0000 Uani . U . . . . . C7 C 0.0334(3) 0.2777(6) 0.5216(3) 0.0117 1.0000 Uani . U . . . . . C8 C 0.0768(3) 0.2222(6) 0.5545(3) 0.0090 1.0000 Uani . U . . . . . C9 C 0.1206(3) 0.1845(6) 0.5219(3) 0.0137 1.0000 Uani . U . . . . . C10 C 0.1190(3) 0.2040(6) 0.4599(3) 0.0117 1.0000 Uani . U . . . . . C11 C 0.1611(3) 0.1659(6) 0.4182(3) 0.0110 1.0000 Uani . U . . . . . C12 C 0.2077(3) 0.1065(6) 0.4377(3) 0.0127 1.0000 Uani . U . . . . . C13 C 0.2450(3) 0.0760(6) 0.3962(3) 0.0152 1.0000 Uani . U . . . . . C14 C 0.2327(3) 0.1045(6) 0.3345(3) 0.0148 1.0000 Uani . U . . . . . C15 C 0.1859(3) 0.1610(6) 0.3176(3) 0.0137 1.0000 Uani . U . . . . . C16 C 0.0761(3) 0.2087(6) 0.6229(3) 0.0085 1.0000 Uani . U . . . . . C17 C 0.0337(3) 0.2509(6) 0.6553(3) 0.0127 1.0000 Uani . U . . . . . C18 C 0.0352(2) 0.2463(6) 0.7190(3) 0.0118 1.0000 Uani . U . . . . . C19 C 0.1175(3) 0.1524(6) 0.7216(3) 0.0119 1.0000 Uani . U . . . . . C20 C 0.1188(3) 0.1577(6) 0.6577(3) 0.0114 1.0000 Uani . U . . . . . C21 C 0.3061(3) 0.3645(6) 0.3694(3) 0.0165 1.0000 Uani . U . . . . . C22 C 0.2564(3) 0.4077(7) 0.3853(3) 0.0179 1.0000 Uani . U . . . . . C23 C 0.2442(3) 0.4034(7) 0.4457(3) 0.0197 1.0000 Uani . U . . . . . C24 C 0.2808(3) 0.3575(6) 0.4896(3) 0.0160 1.0000 Uani . U . . . . . C25 C 0.3292(3) 0.3140(6) 0.4702(3) 0.0129 1.0000 Uani . U . . . . . C26 C 0.3723(3) 0.2665(6) 0.5145(3) 0.0117 1.0000 Uani . U . . . . . C27 C 0.3698(3) 0.2564(6) 0.5773(3) 0.0142 1.0000 Uani . U . . . . . C28 C 0.4165(3) 0.2230(6) 0.6127(3) 0.0140 1.0000 Uani . U . . . . . C29 C 0.4619(3) 0.1940(6) 0.5821(3) 0.0150 1.0000 Uani . U . . . . . C30 C 0.4606(3) 0.2004(6) 0.5185(3) 0.0124 1.0000 Uani . U . . . . . C31 C 0.5051(3) 0.1705(6) 0.4788(3) 0.0137 1.0000 Uani . U . . . . . C32 C 0.5524(3) 0.1218(7) 0.5012(3) 0.0177 1.0000 Uani . U . . . . . C33 C 0.5909(3) 0.0934(7) 0.4601(3) 0.0203 1.0000 Uani . U . . . . . C34 C 0.5792(3) 0.1115(7) 0.3980(3) 0.0192 1.0000 Uani . U . . . . . C35 C 0.5296(3) 0.1576(6) 0.3787(3) 0.0171 1.0000 Uani . U . . . . . C36 C 0.4172(3) 0.2203(6) 0.6781(3) 0.0132 1.0000 Uani . U . . . . . C37 C 0.3781(3) 0.2867(7) 0.7097(3) 0.0161 1.0000 Uani . U . . . . . C38 C 0.3790(3) 0.2902(7) 0.7741(3) 0.0156 1.0000 Uani . U . . . . . C39 C 0.4539(3) 0.1644(7) 0.7795(3) 0.0169 1.0000 Uani . U . . . . . C40 C 0.4546(3) 0.1587(7) 0.7162(3) 0.0160 1.0000 Uani . U . . . . . C41 C 0.6440(3) 0.3847(6) 0.3483(3) 0.0158 1.0000 Uani . U . . . . . C42 C 0.5960(3) 0.4369(6) 0.3623(3) 0.0163 1.0000 Uani . U . . . . . C43 C 0.5840(3) 0.4449(6) 0.4238(3) 0.0174 1.0000 Uani . U . . . . . C44 C 0.6202(3) 0.4017(6) 0.4695(3) 0.0133 1.0000 Uani . U . . . . . C45 C 0.6672(3) 0.3505(6) 0.4518(3) 0.0110 1.0000 Uani . U . . . . . C46 C 0.7095(3) 0.3032(6) 0.4955(3) 0.0110 1.0000 Uani . U . . . . . C47 C 0.7076(3) 0.2977(6) 0.5588(3) 0.0132 1.0000 Uani . U . . . . . C48 C 0.7533(2) 0.2595(6) 0.5947(3) 0.0091 1.0000 Uani . U . . . . . C49 C 0.7986(3) 0.2244(6) 0.5655(3) 0.0119 1.0000 Uani . U . . . . . C50 C 0.7972(3) 0.2307(6) 0.5018(3) 0.0131 1.0000 Uani . U . . . . . C51 C 0.8399(3) 0.1897(6) 0.4626(3) 0.0128 1.0000 Uani . U . . . . . C52 C 0.8879(3) 0.1414(6) 0.4862(3) 0.0125 1.0000 Uani . U . . . . . C53 C 0.9259(3) 0.1044(6) 0.4450(3) 0.0156 1.0000 Uani . U . . . . . C54 C 0.9144(3) 0.1189(6) 0.3826(3) 0.0165 1.0000 Uani . U . . . . . C55 C 0.8652(3) 0.1666(6) 0.3626(3) 0.0162 1.0000 Uani . U . . . . . C56 C 0.7520(2) 0.2515(5) 0.6630(3) 0.0083 1.0000 Uani . U . . . . . C57 C 0.7137(3) 0.3115(6) 0.6948(3) 0.0134 1.0000 Uani . U . . . . . C58 C 0.7142(3) 0.3020(7) 0.7577(3) 0.0146 1.0000 Uani . U . . . . . C59 C 0.7884(3) 0.1759(6) 0.7598(3) 0.0142 1.0000 Uani . U . . . . . C60 C 0.7902(3) 0.1828(6) 0.6970(3) 0.0128 1.0000 Uani . U . . . . . O1 O 0.1214(2) 0.4862(5) 0.3604(2) 0.0202 1.0000 Uani . U . . . . . O2 O 0.1276(2) 0.5023(5) 0.4607(2) 0.0241 1.0000 Uani . U . . . . . O3 O 0.0766(2) 0.6274(5) 0.4072(2) 0.0293 1.0000 Uani . U . . . . . O4 O 0.0402(2) 0.0679(5) 0.3199(2) 0.0208 1.0000 Uani . U . . . . . O5 O 0.0925(2) -0.0878(5) 0.3450(3) 0.0352 1.0000 Uani . U . . . . . O6 O 0.0374(2) -0.0196(5) 0.4093(2) 0.0266 1.0000 Uani . U . . . . . O7 O 0.4515(2) 0.4652(5) 0.4185(2) 0.0244 1.0000 Uani . U . . . . . O8 O 0.4039(3) 0.6189(9) 0.3844(3) 0.0711 1.0000 Uani . U . . . . . O9 O 0.4800(2) 0.5849(5) 0.3474(2) 0.0252 1.0000 Uani . U . . . . . O10 O 0.3773(2) 0.0451(5) 0.3896(2) 0.0198 1.0000 Uani . U . . . . . O11 O 0.3535(2) -0.0701(6) 0.3125(3) 0.0372 1.0000 Uani . U . . . . . O12 O 0.4364(2) -0.0527(6) 0.3411(3) 0.0393 1.0000 Uani . U . . . . . O13 O 0.7831(2) 0.4849(5) 0.3918(2) 0.0250 1.0000 Uani . U . . . . . O14 O 0.7307(3) 0.6216(8) 0.3512(4) 0.0647 1.0000 Uani . U . . . . . O15 O 0.8100(3) 0.6057(6) 0.3217(3) 0.0432 1.0000 Uani . U . . . . . O16 O 0.7194(2) 0.0518(5) 0.3705(2) 0.0293 1.0000 Uani . U . . . . . O17 O 0.7640(3) -0.1015(7) 0.4111(3) 0.0531 1.0000 Uani . U . . . . . O18 O 0.7101(2) -0.0005(6) 0.4643(2) 0.0335 1.0000 Uani . U . . . . . O91 O 0.0902(2) 0.6834(6) 0.2703(2) 0.0276 1.0000 Uani . . . . . . . O92 O 0.4199(2) 0.7183(5) 0.2506(2) 0.0288 1.0000 Uani . . . . . . . O93 O 0.7471(2) 0.8657(6) 0.2705(2) 0.0330 1.0000 Uani . . . . . . . H1 H 0.0986 0.6267 0.2937 0.0341 1.0000 Uiso R . . . . . . H2 H 0.0904 0.7486 0.2894 0.0341 1.0000 Uiso R . . . . . . H3 H 0.4359 0.6676 0.2726 0.0348 1.0000 Uiso R . . . . . . H4 H 0.4204 0.7856 0.2678 0.0348 1.0000 Uiso R . . . . . . H5 H 0.7438 0.7980 0.2878 0.0393 1.0000 Uiso R . . . . . . H6 H 0.7402 0.9222 0.2945 0.0393 1.0000 Uiso R . . . . . . H11 H -0.0173 0.4268 0.2763 0.0143 1.0000 Uiso R . . . . . . H21 H -0.0990 0.5023 0.3045 0.0153 1.0000 Uiso R . . . . . . H31 H -0.1199 0.4958 0.4082 0.0155 1.0000 Uiso R . . . . . . H41 H -0.0579 0.4071 0.4804 0.0148 1.0000 Uiso R . . . . . . H71 H 0.0027 0.3022 0.5418 0.0118 1.0000 Uiso R . . . . . . H91 H 0.1507 0.1465 0.5423 0.0122 1.0000 Uiso R . . . . . . H121 H 0.2137 0.0858 0.4798 0.0130 1.0000 Uiso R . . . . . . H131 H 0.2778 0.0382 0.4089 0.0132 1.0000 Uiso R . . . . . . H141 H 0.2566 0.0837 0.3041 0.0142 1.0000 Uiso R . . . . . . H151 H 0.1779 0.1805 0.2757 0.0126 1.0000 Uiso R . . . . . . H171 H 0.0034 0.2849 0.6332 0.0125 1.0000 Uiso R . . . . . . H181 H 0.0061 0.2784 0.7398 0.0124 1.0000 Uiso R . . . . . . H191 H 0.1463 0.1146 0.7444 0.0122 1.0000 Uiso R . . . . . . H201 H 0.1487 0.1267 0.6380 0.0115 1.0000 Uiso R . . . . . . H211 H 0.3147 0.3664 0.3276 0.0160 1.0000 Uiso R . . . . . . H221 H 0.2322 0.4408 0.3545 0.0162 1.0000 Uiso R . . . . . . H231 H 0.2102 0.4309 0.4565 0.0166 1.0000 Uiso R . . . . . . H241 H 0.2734 0.3563 0.5318 0.0161 1.0000 Uiso R . . . . . . H271 H 0.3373 0.2706 0.5963 0.0141 1.0000 Uiso R . . . . . . H291 H 0.4935 0.1690 0.6047 0.0151 1.0000 Uiso R . . . . . . H321 H 0.5587 0.1076 0.5440 0.0174 1.0000 Uiso R . . . . . . H331 H 0.6245 0.0612 0.4741 0.0181 1.0000 Uiso R . . . . . . H341 H 0.6047 0.0919 0.3691 0.0179 1.0000 Uiso R . . . . . . H351 H 0.5219 0.1707 0.3361 0.0169 1.0000 Uiso R . . . . . . H371 H 0.3504 0.3289 0.6870 0.0157 1.0000 Uiso R . . . . . . H381 H 0.3524 0.3335 0.7945 0.0157 1.0000 Uiso R . . . . . . H391 H 0.4798 0.1190 0.8036 0.0163 1.0000 Uiso R . . . . . . H401 H 0.4816 0.1113 0.6986 0.0162 1.0000 Uiso R . . . . . . H411 H 0.6526 0.3810 0.3065 0.0146 1.0000 Uiso R . . . . . . H421 H 0.5714 0.4652 0.3308 0.0150 1.0000 Uiso R . . . . . . H431 H 0.5512 0.4804 0.4343 0.0157 1.0000 Uiso R . . . . . . H441 H 0.6131 0.4082 0.5117 0.0145 1.0000 Uiso R . . . . . . H471 H 0.6759 0.3185 0.5779 0.0127 1.0000 Uiso R . . . . . . H491 H 0.8294 0.1952 0.5882 0.0120 1.0000 Uiso R . . . . . . H521 H 0.8947 0.1330 0.5293 0.0141 1.0000 Uiso R . . . . . . H531 H 0.9592 0.0713 0.4595 0.0152 1.0000 Uiso R . . . . . . H541 H 0.9396 0.0966 0.3538 0.0155 1.0000 Uiso R . . . . . . H551 H 0.8570 0.1730 0.3197 0.0152 1.0000 Uiso R . . . . . . H571 H 0.6876 0.3608 0.6732 0.0133 1.0000 Uiso R . . . . . . H581 H 0.6874 0.3433 0.7787 0.0139 1.0000 Uiso R . . . . . . H591 H 0.8143 0.1264 0.7817 0.0138 1.0000 Uiso R . . . . . . H601 H 0.8180 0.1426 0.6772 0.0130 1.0000 Uiso 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 0.0122(4) 0.0171(4) 0.0031(3) 0.0004(3) 0.0009(3) 0.0018(3) Cu2 0.0134(4) 0.0210(4) 0.0041(3) -0.0003(3) 0.0020(3) 0.0006(3) Cu3 0.0129(4) 0.0205(4) 0.0054(4) 0.0015(3) 0.0015(3) 0.0022(3) N1 0.0136(15) 0.022(2) 0.0043(15) -0.0014(17) 0.0001(13) 0.0039(14) N2 0.0100(19) 0.019(2) 0.0045(10) 0.0005(14) -0.0008(12) 0.0001(17) N3 0.0123(14) 0.0166(18) 0.0051(14) 0.0016(16) 0.0018(12) 0.0014(13) N4 0.0113(19) 0.018(2) 0.0032(9) 0.0007(14) 0.0017(12) -0.0040(17) N5 0.012(3) 0.018(2) 0.0124(16) -0.0027(16) 0.0023(18) -0.0007(16) N6 0.012(2) 0.0180(19) 0.017(2) 0.0010(17) 0.0007(18) 0.0010(16) N7 0.0137(13) 0.018(2) 0.0081(15) 0.0000(19) 0.0005(13) 0.0007(15) N8 0.0161(17) 0.017(2) 0.0039(9) -0.0010(15) 0.0032(12) -0.0002(19) N9 0.0133(13) 0.025(2) 0.0056(15) -0.0006(19) 0.0008(12) 0.0001(15) N10 0.017(2) 0.033(3) 0.0039(9) -0.0039(15) 0.0011(13) 0.0011(18) N11 0.023(2) 0.023(2) 0.014(2) -0.0045(17) 0.0029(19) 0.0023(18) N12 0.0213(18) 0.020(2) 0.016(2) -0.0012(17) -0.0021(19) 0.002(2) N13 0.0109(14) 0.026(2) 0.0060(15) 0.0034(18) 0.0014(13) -0.0003(15) N14 0.0147(18) 0.015(2) 0.0058(9) 0.0032(15) 0.0023(12) 0.0029(18) N15 0.0145(14) 0.029(2) 0.0030(15) 0.0007(19) 0.0014(13) 0.0043(16) N16 0.015(2) 0.026(2) 0.0059(9) -0.0034(14) 0.0009(13) -0.0004(18) N17 0.016(2) 0.023(2) 0.015(3) 0.0014(17) -0.0051(18) 0.0037(19) N18 0.015(3) 0.025(2) 0.0112(18) 0.0003(18) -0.0033(18) -0.0004(17) C1 0.017(2) 0.020(3) 0.006(2) 0.001(2) -0.0012(17) 0.003(2) C2 0.015(2) 0.017(3) 0.015(2) -0.002(2) -0.004(2) 0.003(2) C3 0.010(2) 0.021(3) 0.020(2) 0.001(2) 0.0029(19) 0.001(2) C4 0.013(2) 0.018(3) 0.012(2) 0.000(2) 0.0049(17) 0.001(2) C5 0.013(2) 0.020(3) 0.0046(16) -0.001(2) -0.0001(15) 0.004(2) C6 0.007(2) 0.022(3) 0.0047(15) -0.001(2) -0.0022(14) -0.0024(19) C7 0.016(2) 0.014(3) 0.0054(15) -0.001(2) 0.0000(17) 0.003(2) C8 0.011(2) 0.013(3) 0.0031(15) -0.0017(19) -0.0006(14) -0.003(2) C9 0.012(2) 0.023(3) 0.0055(15) -0.001(2) 0.0005(17) 0.002(2) C10 0.011(2) 0.018(3) 0.0061(15) 0.001(2) 0.0004(14) 0.003(2) C11 0.0122(18) 0.016(2) 0.0053(14) 0.0026(17) 0.0026(13) -0.0001(17) C12 0.013(2) 0.019(2) 0.0073(19) 0.0001(19) 0.0026(15) 0.0018(18) C13 0.015(2) 0.019(2) 0.0113(19) -0.0027(19) 0.0052(17) 0.002(2) C14 0.0128(19) 0.022(2) 0.0110(18) 0.000(2) 0.0087(18) -0.0032(18) C15 0.0154(19) 0.019(2) 0.0070(18) -0.0011(19) 0.0052(15) -0.0026(18) C16 0.012(2) 0.010(2) 0.0035(15) -0.0018(19) 0.0008(14) -0.002(2) C17 0.013(2) 0.019(3) 0.0055(16) -0.001(2) 0.0009(17) 0.002(2) C18 0.008(2) 0.022(3) 0.0055(15) -0.003(2) 0.0032(16) 0.000(2) C19 0.013(2) 0.019(3) 0.0041(15) -0.003(2) -0.0018(17) 0.001(2) C20 0.015(2) 0.015(3) 0.0044(16) -0.002(2) 0.0009(17) 0.002(2) C21 0.019(2) 0.017(3) 0.013(2) 0.004(2) -0.0008(17) 0.003(2) C22 0.017(2) 0.019(3) 0.018(2) 0.006(3) -0.003(2) 0.002(2) C23 0.018(3) 0.022(3) 0.019(2) 0.001(3) -0.0002(19) 0.004(2) C24 0.015(2) 0.021(3) 0.013(2) 0.000(2) 0.0025(17) 0.001(2) C25 0.015(2) 0.015(3) 0.0090(16) 0.001(2) 0.0020(14) 0.000(2) C26 0.0130(19) 0.015(3) 0.0070(15) 0.000(2) 0.0024(13) -0.001(2) C27 0.016(2) 0.020(3) 0.0071(15) 0.000(2) 0.0023(16) 0.001(2) C28 0.014(2) 0.018(3) 0.0104(15) 0.006(2) 0.0031(14) -0.001(2) C29 0.018(2) 0.020(3) 0.0077(15) -0.002(2) 0.0009(17) 0.004(2) C30 0.0175(19) 0.012(3) 0.0075(14) -0.003(2) 0.0010(13) 0.000(2) C31 0.015(2) 0.020(3) 0.0054(15) -0.005(2) -0.0014(14) -0.001(2) C32 0.018(2) 0.025(3) 0.009(2) 0.000(2) 0.0000(17) 0.003(2) C33 0.020(3) 0.025(3) 0.017(2) -0.002(3) 0.0036(19) 0.005(3) C34 0.019(2) 0.025(3) 0.015(2) -0.003(2) 0.007(2) 0.001(3) C35 0.020(2) 0.019(3) 0.012(2) -0.001(2) 0.0068(16) 0.001(2) C36 0.017(2) 0.013(3) 0.0096(15) -0.004(2) 0.0007(16) 0.000(2) C37 0.022(3) 0.017(3) 0.0093(16) -0.001(2) 0.002(2) 0.005(2) C38 0.014(3) 0.023(3) 0.0099(16) -0.003(2) 0.0048(19) 0.001(2) C39 0.014(3) 0.029(3) 0.0074(16) -0.001(2) -0.001(2) 0.003(2) C40 0.018(3) 0.023(3) 0.0076(16) -0.003(2) 0.0011(19) 0.003(2) C41 0.016(2) 0.022(3) 0.009(2) -0.001(2) -0.0043(17) -0.001(2) C42 0.016(2) 0.019(3) 0.013(2) 0.003(2) -0.005(2) 0.000(2) C43 0.017(3) 0.018(3) 0.017(2) 0.001(2) -0.0007(19) 0.004(2) C44 0.013(2) 0.018(3) 0.009(2) -0.002(2) 0.0012(17) -0.001(2) C45 0.011(2) 0.016(3) 0.0064(15) -0.001(2) 0.0006(14) -0.0033(19) C46 0.0130(19) 0.014(3) 0.0061(14) 0.000(2) 0.0018(14) -0.001(2) C47 0.014(2) 0.020(3) 0.0055(15) -0.004(2) 0.0001(16) -0.002(2) C48 0.015(2) 0.006(2) 0.0060(15) -0.0023(19) 0.0012(14) -0.003(2) C49 0.017(2) 0.014(3) 0.0056(15) 0.003(2) 0.0027(16) 0.001(2) C50 0.017(2) 0.017(3) 0.0052(14) 0.000(2) 0.0008(14) 0.005(2) C51 0.015(2) 0.020(3) 0.0038(15) 0.003(2) 0.0018(14) 0.002(2) C52 0.014(2) 0.015(3) 0.008(2) 0.001(2) -0.0001(16) 0.001(2) C53 0.014(2) 0.018(3) 0.015(2) 0.000(2) 0.0034(19) -0.001(2) C54 0.014(2) 0.023(3) 0.013(2) -0.003(2) 0.005(2) -0.004(2) C55 0.018(2) 0.022(3) 0.009(2) -0.004(2) 0.0048(16) 0.000(2) C56 0.015(2) 0.004(2) 0.0063(15) -0.0005(18) 0.0017(16) 0.0002(19) C57 0.016(3) 0.016(3) 0.0080(16) -0.004(2) 0.0021(19) 0.003(2) C58 0.013(3) 0.023(3) 0.0081(16) -0.002(2) 0.0033(19) 0.000(2) C59 0.015(3) 0.021(3) 0.0063(16) -0.002(2) -0.0029(19) 0.004(2) C60 0.017(3) 0.015(3) 0.0060(16) -0.004(2) -0.0032(19) 0.004(2) O1 0.025(2) 0.0185(14) 0.0186(18) -0.0055(15) 0.0104(18) -0.0031(14) O2 0.020(3) 0.034(3) 0.0188(18) 0.005(2) -0.0013(19) 0.004(2) O3 0.029(3) 0.037(3) 0.022(3) 0.002(2) 0.004(2) 0.018(2) O4 0.027(2) 0.0192(13) 0.0156(19) 0.0015(13) -0.0061(18) -0.0032(13) O5 0.025(3) 0.032(3) 0.049(4) -0.013(3) 0.003(2) 0.011(2) O6 0.030(3) 0.036(3) 0.014(2) 0.001(2) 0.0022(19) -0.001(2) O7 0.024(2) 0.0237(13) 0.025(2) 0.0011(14) -0.001(2) -0.0064(15) O8 0.060(4) 0.120(7) 0.037(4) 0.048(4) 0.033(3) 0.063(4) O9 0.020(2) 0.032(3) 0.024(3) 0.002(2) 0.0041(18) 0.001(2) O10 0.021(2) 0.0217(14) 0.017(2) -0.0021(14) 0.0022(17) -0.0021(14) O11 0.040(3) 0.036(3) 0.034(3) -0.011(2) -0.009(2) -0.012(3) O12 0.028(2) 0.051(4) 0.039(3) -0.002(3) 0.009(2) 0.015(3) O13 0.029(2) 0.0258(12) 0.019(2) 0.0075(14) -0.009(2) -0.0100(16) O14 0.032(3) 0.085(6) 0.076(5) 0.001(4) -0.008(3) 0.035(3) O15 0.048(3) 0.055(4) 0.027(3) 0.018(3) 0.015(3) 0.000(3) O16 0.043(3) 0.0241(13) 0.0188(19) 0.0053(15) -0.011(2) -0.0083(16) O17 0.060(4) 0.085(5) 0.013(3) 0.000(3) 0.004(3) 0.053(4) O18 0.023(3) 0.059(4) 0.019(2) 0.003(2) 0.005(2) 0.017(3) O91 0.026(3) 0.041(3) 0.016(3) 0.003(2) 0.004(2) 0.002(2) O92 0.035(3) 0.034(3) 0.016(2) 0.001(2) -0.006(2) 0.006(3) O93 0.041(3) 0.038(3) 0.020(3) -0.001(2) -0.003(3) 0.001(3) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.02944(6) loop_ _oxford_twin_element_scale_factors 0.7627(12) 0.2373(12) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Cu1 . N4 4_554 1.968(5) yes Cu1 . N1 . 2.051(5) yes Cu1 . N2 . 1.907(5) yes Cu1 . N3 . 2.042(5) yes Cu1 . O1 . 2.462(5) yes Cu1 . O4 . 2.566(5) yes Cu2 . N10 4_554 1.987(5) yes Cu2 . N7 . 2.048(5) yes Cu2 . N8 . 1.928(5) yes Cu2 . N9 . 2.054(6) yes Cu2 . O7 . 2.472(5) yes Cu2 . O10 . 2.482(5) yes Cu3 . N16 4_554 1.961(5) yes Cu3 . N13 . 2.032(6) yes Cu3 . N14 . 1.926(5) yes Cu3 . N15 . 2.061(6) yes Cu3 . O13 . 2.456(5) yes Cu3 . O16 . 2.515(5) yes N1 . C1 . 1.333(8) yes N1 . C5 . 1.366(8) yes N2 . C6 . 1.349(8) yes N2 . C10 . 1.357(8) yes N3 . C11 . 1.358(8) yes N3 . C15 . 1.350(8) yes N4 . C18 . 1.352(8) yes N4 . C19 . 1.340(8) yes N5 . O1 . 1.286(7) yes N5 . O2 . 1.247(7) yes N5 . O3 . 1.243(8) yes N6 . O4 . 1.268(7) yes N6 . O5 . 1.247(8) yes N6 . O6 . 1.251(8) yes N7 . C21 . 1.350(8) yes N7 . C25 . 1.356(8) yes N8 . C26 . 1.348(9) yes N8 . C30 . 1.340(9) yes N9 . C31 . 1.362(8) yes N9 . C35 . 1.331(9) yes N10 . C38 . 1.350(9) yes N10 . C39 . 1.330(9) yes N11 . O7 . 1.241(8) yes N11 . O8 . 1.251(9) yes N11 . O9 . 1.256(8) yes N12 . O10 . 1.262(8) yes N12 . O11 . 1.229(8) yes N12 . O12 . 1.238(8) yes N13 . C41 . 1.347(8) yes N13 . C45 . 1.375(8) yes N14 . C46 . 1.339(8) yes N14 . C50 . 1.339(8) yes N15 . C51 . 1.368(8) yes N15 . C55 . 1.336(9) yes N16 . C58 . 1.360(9) yes N16 . C59 . 1.342(9) yes N17 . O13 . 1.255(7) yes N17 . O14 . 1.232(8) yes N17 . O15 . 1.229(8) yes N18 . O16 . 1.257(8) yes N18 . O17 . 1.240(9) yes N18 . O18 . 1.228(8) yes C1 . C2 . 1.385(10) yes C1 . H11 . 0.950 no C2 . C3 . 1.392(10) yes C2 . H21 . 0.950 no C3 . C4 . 1.389(10) yes C3 . H31 . 0.950 no C4 . C5 . 1.394(9) yes C4 . H41 . 0.950 no C5 . C6 . 1.464(9) yes C6 . C7 . 1.382(9) yes C7 . C8 . 1.407(9) yes C7 . H71 . 0.950 no C8 . C9 . 1.409(9) yes C8 . C16 . 1.500(8) yes C9 . C10 . 1.366(9) yes C9 . H91 . 0.950 no C10 . C11 . 1.496(9) yes C11 . C12 . 1.383(9) yes C12 . C13 . 1.381(9) yes C12 . H121 . 0.950 no C13 . C14 . 1.397(9) yes C13 . H131 . 0.950 no C14 . C15 . 1.360(10) yes C14 . H141 . 0.950 no C15 . H151 . 0.950 no C16 . C17 . 1.392(9) yes C16 . C20 . 1.394(9) yes C17 . C18 . 1.391(8) yes C17 . H171 . 0.950 no C18 . H181 . 0.950 no C19 . C20 . 1.398(8) yes C19 . H191 . 0.950 no C20 . H201 . 0.950 no C21 . C22 . 1.399(10) yes C21 . H211 . 0.950 no C22 . C23 . 1.371(11) yes C22 . H221 . 0.950 no C23 . C24 . 1.382(10) yes C23 . H231 . 0.950 no C24 . C25 . 1.395(9) yes C24 . H241 . 0.950 no C25 . C26 . 1.501(9) yes C26 . C27 . 1.380(8) yes C27 . C28 . 1.416(9) yes C27 . H271 . 0.950 no C28 . C29 . 1.395(10) yes C28 . C36 . 1.426(8) yes C29 . C30 . 1.388(9) yes C29 . H291 . 0.950 no C30 . C31 . 1.490(9) yes C31 . C32 . 1.366(10) yes C32 . C33 . 1.394(10) yes C32 . H321 . 0.950 no C33 . C34 . 1.383(10) yes C33 . H331 . 0.950 no C34 . C35 . 1.386(10) yes C34 . H341 . 0.950 no C35 . H351 . 0.950 no C36 . C37 . 1.428(10) yes C36 . C40 . 1.390(9) yes C37 . C38 . 1.405(9) yes C37 . H371 . 0.950 no C38 . H381 . 0.950 no C39 . C40 . 1.385(9) yes C39 . H391 . 0.950 no C40 . H401 . 0.950 no C41 . C42 . 1.385(10) yes C41 . H411 . 0.950 no C42 . C43 . 1.396(10) yes C42 . H421 . 0.950 no C43 . C44 . 1.393(9) yes C43 . H431 . 0.950 no C44 . C45 . 1.383(9) yes C44 . H441 . 0.950 no C45 . C46 . 1.479(9) yes C46 . C47 . 1.385(9) yes C47 . C48 . 1.416(9) yes C47 . H471 . 0.950 no C48 . C49 . 1.391(9) yes C48 . C56 . 1.494(8) yes C49 . C50 . 1.390(8) yes C49 . H491 . 0.950 no C50 . C51 . 1.481(9) yes C51 . C52 . 1.389(9) yes C52 . C53 . 1.410(9) yes C52 . H521 . 0.950 no C53 . C54 . 1.384(10) yes C53 . H531 . 0.950 no C54 . C55 . 1.388(10) yes C54 . H541 . 0.950 no C55 . H551 . 0.950 no C56 . C57 . 1.383(9) yes C56 . C60 . 1.395(9) yes C57 . C58 . 1.376(9) yes C57 . H571 . 0.950 no C58 . H581 . 0.950 no C59 . C60 . 1.376(9) yes C59 . H591 . 0.950 no C60 . H601 . 0.950 no O91 . H1 . 0.820 no O91 . H2 . 0.820 no O92 . H3 . 0.820 no O92 . H4 . 0.820 no O93 . H5 . 0.830 no O93 . H6 . 0.830 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag N4 4_554 Cu1 . N1 . 98.9(2) yes N4 4_554 Cu1 . N2 . 176.0(2) yes N1 . Cu1 . N2 . 79.7(2) yes N4 4_554 Cu1 . N3 . 101.0(2) yes N1 . Cu1 . N3 . 160.1(2) yes N2 . Cu1 . N3 . 80.4(2) yes N4 4_554 Cu1 . O1 . 93.2(2) yes N1 . Cu1 . O1 . 88.3(2) yes N2 . Cu1 . O1 . 90.5(2) yes N3 . Cu1 . O1 . 91.8(2) yes N4 4_554 Cu1 . O4 . 85.4(2) yes N1 . Cu1 . O4 . 95.0(2) yes N2 . Cu1 . O4 . 91.0(2) yes N3 . Cu1 . O4 . 85.45(19) yes O1 . Cu1 . O4 . 176.63(16) yes N10 4_554 Cu2 . N7 . 99.7(2) yes N10 4_554 Cu2 . N8 . 179.4(3) yes N7 . Cu2 . N8 . 80.3(2) yes N10 4_554 Cu2 . N9 . 100.1(2) yes N7 . Cu2 . N9 . 160.1(2) yes N8 . Cu2 . N9 . 79.9(2) yes N10 4_554 Cu2 . O7 . 94.7(2) yes N7 . Cu2 . O7 . 89.0(2) yes N8 . Cu2 . O7 . 85.9(2) yes N9 . Cu2 . O7 . 89.2(2) yes N10 4_554 Cu2 . O10 . 91.5(2) yes N7 . Cu2 . O10 . 86.3(2) yes N8 . Cu2 . O10 . 87.9(2) yes N9 . Cu2 . O10 . 93.5(2) yes O7 . Cu2 . O10 . 172.76(17) yes N16 4_554 Cu3 . N13 . 99.7(2) yes N16 4_554 Cu3 . N14 . 177.6(3) yes N13 . Cu3 . N14 . 80.7(2) yes N16 4_554 Cu3 . N15 . 99.4(2) yes N13 . Cu3 . N15 . 160.9(2) yes N14 . Cu3 . N15 . 80.2(2) yes N16 4_554 Cu3 . O13 . 96.8(2) yes N13 . Cu3 . O13 . 84.9(2) yes N14 . Cu3 . O13 . 85.6(2) yes N15 . Cu3 . O13 . 92.2(2) yes N16 4_554 Cu3 . O16 . 84.0(2) yes N13 . Cu3 . O16 . 93.2(2) yes N14 . Cu3 . O16 . 93.6(2) yes N15 . Cu3 . O16 . 89.4(2) yes O13 . Cu3 . O16 . 178.0(2) yes Cu1 . N1 . C1 . 128.3(4) yes Cu1 . N1 . C5 . 112.7(4) yes C1 . N1 . C5 . 119.0(6) yes Cu1 . N2 . C6 . 120.9(4) yes Cu1 . N2 . C10 . 120.1(4) yes C6 . N2 . C10 . 118.9(5) yes Cu1 . N3 . C11 . 113.7(4) yes Cu1 . N3 . C15 . 128.6(4) yes C11 . N3 . C15 . 117.6(5) yes Cu1 4_555 N4 . C18 . 117.7(4) yes Cu1 4_555 N4 . C19 . 124.0(4) yes C18 . N4 . C19 . 117.9(5) yes O1 . N5 . O2 . 119.8(5) yes O1 . N5 . O3 . 119.7(5) yes O2 . N5 . O3 . 120.5(6) yes O4 . N6 . O5 . 120.9(6) yes O4 . N6 . O6 . 119.3(6) yes O5 . N6 . O6 . 119.8(6) yes Cu2 . N7 . C21 . 129.0(5) yes Cu2 . N7 . C25 . 113.7(4) yes C21 . N7 . C25 . 117.2(6) yes Cu2 . N8 . C26 . 119.7(4) yes Cu2 . N8 . C30 . 119.8(4) yes C26 . N8 . C30 . 120.5(5) yes Cu2 . N9 . C31 . 113.7(4) yes Cu2 . N9 . C35 . 128.3(4) yes C31 . N9 . C35 . 118.0(6) yes Cu2 4_555 N10 . C38 . 116.8(5) yes Cu2 4_555 N10 . C39 . 122.9(5) yes C38 . N10 . C39 . 120.3(5) yes O7 . N11 . O8 . 120.0(6) yes O7 . N11 . O9 . 121.3(6) yes O8 . N11 . O9 . 118.7(6) yes O10 . N12 . O11 . 119.4(6) yes O10 . N12 . O12 . 119.1(6) yes O11 . N12 . O12 . 121.4(6) yes Cu3 . N13 . C41 . 128.6(4) yes Cu3 . N13 . C45 . 113.6(4) yes C41 . N13 . C45 . 117.6(6) yes Cu3 . N14 . C46 . 118.4(4) yes Cu3 . N14 . C50 . 119.8(4) yes C46 . N14 . C50 . 121.8(6) yes Cu3 . N15 . C51 . 112.5(4) yes Cu3 . N15 . C55 . 129.1(4) yes C51 . N15 . C55 . 118.3(6) yes Cu3 4_555 N16 . C58 . 121.1(4) yes Cu3 4_555 N16 . C59 . 121.0(4) yes C58 . N16 . C59 . 117.9(6) yes O13 . N17 . O14 . 118.9(7) yes O13 . N17 . O15 . 120.1(6) yes O14 . N17 . O15 . 121.0(7) yes O16 . N18 . O17 . 120.2(6) yes O16 . N18 . O18 . 119.9(6) yes O17 . N18 . O18 . 120.0(6) yes N1 . C1 . C2 . 122.3(6) yes N1 . C1 . H11 . 118.6 no C2 . C1 . H11 . 119.1 no C1 . C2 . C3 . 119.7(6) yes C1 . C2 . H21 . 120.4 no C3 . C2 . H21 . 119.9 no C2 . C3 . C4 . 118.2(6) yes C2 . C3 . H31 . 121.0 no C4 . C3 . H31 . 120.8 no C3 . C4 . C5 . 119.6(6) yes C3 . C4 . H41 . 120.4 no C5 . C4 . H41 . 120.0 no C4 . C5 . N1 . 121.2(6) yes C4 . C5 . C6 . 123.3(6) yes N1 . C5 . C6 . 115.5(6) yes C5 . C6 . N2 . 111.1(5) yes C5 . C6 . C7 . 127.3(6) yes N2 . C6 . C7 . 121.5(6) yes C6 . C7 . C8 . 119.6(6) yes C6 . C7 . H71 . 119.6 no C8 . C7 . H71 . 120.8 no C7 . C8 . C9 . 118.3(6) yes C7 . C8 . C16 . 119.7(6) yes C9 . C8 . C16 . 122.0(6) yes C8 . C9 . C10 . 118.5(6) yes C8 . C9 . H91 . 121.0 no C10 . C9 . H91 . 120.5 no C9 . C10 . N2 . 123.1(6) yes C9 . C10 . C11 . 125.4(6) yes N2 . C10 . C11 . 111.4(5) yes C10 . C11 . N3 . 114.3(5) yes C10 . C11 . C12 . 124.0(5) yes N3 . C11 . C12 . 121.6(6) yes C11 . C12 . C13 . 120.4(6) yes C11 . C12 . H121 . 119.4 no C13 . C12 . H121 . 120.2 no C12 . C13 . C14 . 117.3(6) yes C12 . C13 . H131 . 121.7 no C14 . C13 . H131 . 121.0 no C13 . C14 . C15 . 120.0(6) yes C13 . C14 . H141 . 120.5 no C15 . C14 . H141 . 119.5 no C14 . C15 . N3 . 123.0(6) yes C14 . C15 . H151 . 119.5 no N3 . C15 . H151 . 117.5 no C8 . C16 . C17 . 121.8(6) yes C8 . C16 . C20 . 121.7(6) yes C17 . C16 . C20 . 116.4(5) yes C16 . C17 . C18 . 121.2(6) yes C16 . C17 . H171 . 119.1 no C18 . C17 . H171 . 119.7 no C17 . C18 . N4 . 121.6(6) yes C17 . C18 . H181 . 119.1 no N4 . C18 . H181 . 119.3 no N4 . C19 . C20 . 123.0(6) yes N4 . C19 . H191 . 118.3 no C20 . C19 . H191 . 118.7 no C19 . C20 . C16 . 119.8(6) yes C19 . C20 . H201 . 120.0 no C16 . C20 . H201 . 120.2 no N7 . C21 . C22 . 122.6(6) yes N7 . C21 . H211 . 118.0 no C22 . C21 . H211 . 119.3 no C21 . C22 . C23 . 118.8(7) yes C21 . C22 . H221 . 119.7 no C23 . C22 . H221 . 121.4 no C22 . C23 . C24 . 120.0(7) yes C22 . C23 . H231 . 118.9 no C24 . C23 . H231 . 121.1 no C23 . C24 . C25 . 118.1(6) yes C23 . C24 . H241 . 121.0 no C25 . C24 . H241 . 120.9 no C24 . C25 . N7 . 123.2(6) yes C24 . C25 . C26 . 122.2(6) yes N7 . C25 . C26 . 114.5(6) yes C25 . C26 . N8 . 111.8(5) yes C25 . C26 . C27 . 126.3(6) yes N8 . C26 . C27 . 121.9(6) yes C26 . C27 . C28 . 118.4(6) yes C26 . C27 . H271 . 120.8 no C28 . C27 . H271 . 120.8 no C27 . C28 . C29 . 118.4(6) yes C27 . C28 . C36 . 120.9(6) yes C29 . C28 . C36 . 120.7(6) yes C28 . C29 . C30 . 119.7(6) yes C28 . C29 . H291 . 120.0 no C30 . C29 . H291 . 120.2 no C29 . C30 . N8 . 120.9(6) yes C29 . C30 . C31 . 126.5(6) yes N8 . C30 . C31 . 112.6(5) yes C30 . C31 . N9 . 114.0(6) yes C30 . C31 . C32 . 123.0(6) yes N9 . C31 . C32 . 122.8(6) yes C31 . C32 . C33 . 118.6(6) yes C31 . C32 . H321 . 120.4 no C33 . C32 . H321 . 121.0 no C32 . C33 . C34 . 118.9(7) yes C32 . C33 . H331 . 121.0 no C34 . C33 . H331 . 120.1 no C33 . C34 . C35 . 119.0(6) yes C33 . C34 . H341 . 120.4 no C35 . C34 . H341 . 120.7 no C34 . C35 . N9 . 122.6(6) yes C34 . C35 . H351 . 118.6 no N9 . C35 . H351 . 118.8 no C28 . C36 . C37 . 120.2(6) yes C28 . C36 . C40 . 125.3(6) yes C37 . C36 . C40 . 114.5(6) yes C36 . C37 . C38 . 121.8(6) yes C36 . C37 . H371 . 119.9 no C38 . C37 . H371 . 118.3 no C37 . C38 . N10 . 119.5(6) yes C37 . C38 . H381 . 120.8 no N10 . C38 . H381 . 119.6 no N10 . C39 . C40 . 121.9(6) yes N10 . C39 . H391 . 119.4 no C40 . C39 . H391 . 118.7 no C36 . C40 . C39 . 121.9(6) yes C36 . C40 . H401 . 119.5 no C39 . C40 . H401 . 118.6 no N13 . C41 . C42 . 122.9(6) yes N13 . C41 . H411 . 118.5 no C42 . C41 . H411 . 118.7 no C41 . C42 . C43 . 118.6(6) yes C41 . C42 . H421 . 120.8 no C43 . C42 . H421 . 120.5 no C42 . C43 . C44 . 119.8(7) yes C42 . C43 . H431 . 119.7 no C44 . C43 . H431 . 120.4 no C43 . C44 . C45 . 118.1(6) yes C43 . C44 . H441 . 121.0 no C45 . C44 . H441 . 120.9 no C44 . C45 . N13 . 123.0(6) yes C44 . C45 . C46 . 123.7(6) yes N13 . C45 . C46 . 113.4(6) yes C45 . C46 . N14 . 113.6(5) yes C45 . C46 . C47 . 126.3(6) yes N14 . C46 . C47 . 120.0(6) yes C46 . C47 . C48 . 119.4(6) yes C46 . C47 . H471 . 120.4 no C48 . C47 . H471 . 120.2 no C47 . C48 . C49 . 119.1(6) yes C47 . C48 . C56 . 120.2(5) yes C49 . C48 . C56 . 120.6(5) yes C48 . C49 . C50 . 118.1(6) yes C48 . C49 . H491 . 121.1 no C50 . C49 . H491 . 120.8 no C49 . C50 . N14 . 121.6(6) yes C49 . C50 . C51 . 125.9(6) yes N14 . C50 . C51 . 112.4(5) yes C50 . C51 . N15 . 115.0(5) yes C50 . C51 . C52 . 123.0(5) yes N15 . C51 . C52 . 122.0(6) yes C51 . C52 . C53 . 118.6(6) yes C51 . C52 . H521 . 120.4 no C53 . C52 . H521 . 121.0 no C52 . C53 . C54 . 119.0(6) yes C52 . C53 . H531 . 120.8 no C54 . C53 . H531 . 120.2 no C53 . C54 . C55 . 118.8(6) yes C53 . C54 . H541 . 120.8 no C55 . C54 . H541 . 120.4 no C54 . C55 . N15 . 123.2(6) yes C54 . C55 . H551 . 118.4 no N15 . C55 . H551 . 118.4 no C48 . C56 . C57 . 122.0(6) yes C48 . C56 . C60 . 120.4(5) yes C57 . C56 . C60 . 117.6(6) yes C56 . C57 . C58 . 120.0(6) yes C56 . C57 . H571 . 119.8 no C58 . C57 . H571 . 120.2 no C57 . C58 . N16 . 122.2(6) yes C57 . C58 . H581 . 118.8 no N16 . C58 . H581 . 119.0 no N16 . C59 . C60 . 122.5(6) yes N16 . C59 . H591 . 119.4 no C60 . C59 . H591 . 118.1 no C56 . C60 . C59 . 119.8(6) yes C56 . C60 . H601 . 120.4 no C59 . C60 . H601 . 119.7 no Cu1 . O1 . N5 . 113.9(4) yes Cu1 . O4 . N6 . 114.1(4) yes Cu2 . O7 . N11 . 126.0(4) yes Cu2 . O10 . N12 . 120.7(4) yes Cu3 . O13 . N17 . 126.6(4) yes Cu3 . O16 . N18 . 114.9(4) yes H1 . O91 . H2 . 109.5 no H3 . O92 . H4 . 109.5 no H5 . O93 . H6 . 109.5 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag O91 . H1 . O1 . 176 0.82 2.16 2.978(9) yes O91 . H1 . O3 . 122 0.82 2.57 3.087(9) yes O91 . H2 . O5 1_565 176 0.82 2.15 2.964(9) yes O92 . H3 . O9 . 162 0.82 2.12 2.910(9) yes O92 . H4 . O11 1_565 137 0.82 2.53 3.184(9) yes O92 . H4 . O12 1_565 163 0.82 2.39 3.182(9) yes O93 . H5 . O14 . 171 0.83 2.39 3.215(9) yes O93 . H6 . O16 1_565 171 0.83 2.26 3.080(9) yes O93 . H6 . O17 1_565 120 0.83 2.59 3.094(9) yes C2 . H21 . O15 1_455 128 0.95 2.60 3.269(9) yes C3 . H31 . O13 1_455 145 0.95 2.45 3.270(9) yes C4 . H41 . O2 2_566 133 0.95 2.44 3.166(9) yes C4 . H41 . O3 2_566 173 0.95 2.55 3.497(9) yes C7 . H71 . O3 2_566 178 0.95 2.46 3.413(9) yes C9 . H91 . O17 2_656 165 0.95 2.37 3.302(9) yes C12 . H121 . O17 2_656 162 0.95 2.42 3.336(9) yes C12 . H121 . O18 2_656 131 0.95 2.40 3.107(9) yes C13 . H131 . O10 . 141 0.95 2.57 3.361(9) yes C15 . H151 . O15 3_645 141 0.95 2.31 3.106(9) yes C17 . H171 . O3 2_566 172 0.95 2.35 3.295(9) yes C18 . H181 . O91 2_566 144 0.95 2.46 3.270(9) yes C20 . H201 . O17 2_656 165 0.95 2.52 3.444(9) yes C21 . H211 . O93 3_645 130 0.95 2.57 3.260(9) yes C23 . H231 . O2 . 168 0.95 2.23 3.162(9) yes C24 . H241 . O14 2_666 169 0.95 2.57 3.511(9) yes C27 . H271 . O14 2_666 160 0.95 2.42 3.323(9) yes C29 . H291 . O12 2_656 165 0.95 2.42 3.347(9) yes C32 . H321 . O12 2_656 172 0.95 2.57 3.516(9) yes C33 . H331 . O18 . 155 0.95 2.28 3.167(9) yes C35 . H351 . O92 3_645 132 0.95 2.51 3.229(9) yes C37 . H371 . O14 2_666 160 0.95 2.22 3.136(9) yes C38 . H381 . O11 4_555 124 0.95 2.59 3.219(9) yes C39 . H391 . O9 4_555 133 0.95 2.41 3.130(9) yes C40 . H401 . O12 2_656 162 0.95 2.37 3.290(9) yes C43 . H431 . O7 . 144 0.95 2.52 3.339(9) yes C44 . H441 . O8 2_666 169 0.95 2.35 3.287(9) yes C47 . H471 . O8 2_666 174 0.95 2.32 3.264(9) yes C52 . H521 . O6 2_656 132 0.95 2.44 3.157(9) yes C53 . H531 . O6 1_655 135 0.95 2.51 3.248(9) yes C55 . H551 . O91 3_645 134 0.95 2.44 3.177(9) yes C57 . H571 . O8 2_666 150 0.95 2.57 3.424(9) yes C60 . H601 . O5 2_656 158 0.95 2.41 3.308(9) yes