# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email s.j.archibald@hull.ac.uk _publ_contact_author_name 'Archibald, Steve' loop_ _publ_author_name J.Silversides R.Smith S.Archibald # Attachment '- compound 11.cif' data_sja23_05 _database_code_depnum_ccdc_archive 'CCDC 803779' #TrackingRef '- compound 11.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21.50 H40.50 Br N4 O2.50' _chemical_formula_weight 474.99 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' Br Br -0.2901 2.4595 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.426(3) _cell_length_b 11.423(4) _cell_length_c 12.534(5) _cell_angle_alpha 63.15(2) _cell_angle_beta 87.27(3) _cell_angle_gamma 81.51(3) _cell_volume 1190.6(7) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6198 _cell_measurement_theta_min 2.75 _cell_measurement_theta_max 26.80 _exptl_crystal_description block _exptl_crystal_colour colourless _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 1.325 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 505 _exptl_absorpt_coefficient_mu 1.752 _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 150(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-II image plate' _diffrn_measurement_method '\w scans, 134 frames at 3\% intervals, exposure time 8 minutes' _diffrn_reflns_number 26864 _diffrn_reflns_av_R_equivalents 0.1153 _diffrn_reflns_av_sigmaI/netI 0.1438 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.76 _diffrn_reflns_theta_max 30.00 _reflns_number_total 6939 _reflns_number_gt 2264 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'X-AREA (Stoe & Cie, 2002)' _computing_cell_refinement X-AREA _computing_data_reduction 'X-RED (Stoe & Cie, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP III (Farrugia, 1997)' _computing_publication_material 'WinGX (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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6939 _refine_ls_number_parameters 277 _refine_ls_number_restraints 11 _refine_ls_R_factor_all 0.2412 _refine_ls_R_factor_gt 0.1073 _refine_ls_wR_factor_ref 0.3685 _refine_ls_wR_factor_gt 0.2958 _refine_ls_goodness_of_fit_ref 0.928 _refine_ls_restrained_S_all 0.937 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4267(8) 0.5915(7) 0.1514(6) 0.0405(15) Uani 1 1 d . . . H1A H 0.3687 0.6215 0.2047 0.049 Uiso 1 1 calc R . . H1B H 0.3608 0.5673 0.1078 0.049 Uiso 1 1 calc R . . C2 C 0.5037(8) 0.7048(7) 0.0614(7) 0.0477(18) Uani 1 1 d . . . H2A H 0.5568 0.6760 0.0054 0.057 Uiso 1 1 calc R . . H2B H 0.4312 0.7817 0.0142 0.057 Uiso 1 1 calc R . . C3 C 0.5373(10) 0.8284(8) 0.1714(9) 0.062(2) Uani 1 1 d . . . H3A H 0.5197 0.9213 0.1085 0.074 Uiso 1 1 calc R . . H3B H 0.4432 0.8002 0.2022 0.074 Uiso 1 1 calc R . . C4 C 0.6184(11) 0.8224(9) 0.2642(10) 0.067(2) Uani 1 1 d . . . H4A H 0.5668 0.8840 0.2935 0.081 Uiso 1 1 calc R . . H4B H 0.7106 0.8544 0.2318 0.081 Uiso 1 1 calc R . . C5 C 0.6486(14) 0.6921(9) 0.3649(7) 0.074(3) Uani 1 1 d . . . H5A H 0.5564 0.6592 0.3955 0.088 Uiso 1 1 calc R . . H5B H 0.6953 0.7012 0.4294 0.088 Uiso 1 1 calc R . . C6 C 0.8899(11) 0.6191(10) 0.3000(9) 0.064(2) Uani 1 1 d . . . H6A H 0.9526 0.5883 0.3715 0.077 Uiso 1 1 calc R . . H6B H 0.8841 0.7167 0.2557 0.077 Uiso 1 1 calc R . . C7 C 0.9569(8) 0.5572(8) 0.2200(7) 0.0475(18) Uani 1 1 d . . . H7A H 1.0371 0.6044 0.1757 0.057 Uiso 1 1 calc R . . H7B H 0.9962 0.4633 0.2704 0.057 Uiso 1 1 calc R . . C8 C 0.8645(9) 0.4443(6) 0.1204(6) 0.0424(16) Uani 1 1 d . . . H8A H 0.9641 0.3981 0.1414 0.051 Uiso 1 1 calc R . . H8B H 0.8459 0.4681 0.0355 0.051 Uiso 1 1 calc R . . C9 C 0.7637(8) 0.3534(7) 0.1963(6) 0.0408(15) Uani 1 1 d . . . H9A H 0.7765 0.3364 0.2802 0.049 Uiso 1 1 calc R . . H9B H 0.7876 0.2677 0.1931 0.049 Uiso 1 1 calc R . . C10 C 0.6083(8) 0.4078(7) 0.1580(6) 0.0389(15) Uani 1 1 d . . . H10A H 0.6045 0.4716 0.0720 0.047 Uiso 1 1 calc R . . H10B H 0.5577 0.3339 0.1670 0.047 Uiso 1 1 calc R . . C11 C 0.7266(7) 0.7972(6) 0.0440(5) 0.0347(14) Uani 1 1 d . . . H11A H 0.7825 0.8377 0.0801 0.042 Uiso 1 1 calc R . . H11B H 0.6893 0.8673 -0.0350 0.042 Uiso 1 1 calc R . . C12 C 0.8262(8) 0.6890(6) 0.0265(6) 0.0391(15) Uani 1 1 d . . . H12A H 0.7840 0.6732 -0.0359 0.047 Uiso 1 1 calc R . . H12B H 0.9195 0.7205 -0.0025 0.047 Uiso 1 1 calc R . . C13 C 0.4705(7) 0.3821(6) 0.3333(5) 0.0334(13) Uani 1 1 d . . . H13A H 0.4231 0.4325 0.3752 0.040 Uiso 1 1 calc R . . H13B H 0.5496 0.3177 0.3861 0.040 Uiso 1 1 calc R . . C14 C 0.3621(8) 0.3056(7) 0.3156(6) 0.0378(15) Uani 1 1 d . . . C15 C 0.2556(7) 0.0999(6) 0.4242(6) 0.0402(16) Uani 1 1 d . . . C16 C 0.3143(12) 0.0448(10) 0.3379(12) 0.081(3) Uani 1 1 d . . . H16A H 0.2980 0.1144 0.2554 0.121 Uiso 1 1 calc R . . H16B H 0.2652 -0.0298 0.3495 0.121 Uiso 1 1 calc R . . H16C H 0.4175 0.0145 0.3533 0.121 Uiso 1 1 calc R . . C17 C 0.2766(10) -0.0035(8) 0.5505(9) 0.075(3) Uani 1 1 d . . . H17A H 0.2404 0.0349 0.6041 0.112 Uiso 1 1 calc R . . H17B H 0.3791 -0.0368 0.5673 0.112 Uiso 1 1 calc R . . H17C H 0.2243 -0.0766 0.5633 0.112 Uiso 1 1 calc R . . C18 C 0.1029(8) 0.1616(7) 0.3956(7) 0.0502(19) Uani 1 1 d . . . H18A H 0.0934 0.2282 0.3116 0.075 Uiso 1 1 calc R . . H18B H 0.0717 0.2041 0.4470 0.075 Uiso 1 1 calc R . . H18C H 0.0430 0.0931 0.4092 0.075 Uiso 1 1 calc R . . Br1 Br 0.23277(15) 0.67631(10) 0.42007(10) 0.0872(5) Uani 1 1 d . . . N1 N 0.5314(6) 0.4736(5) 0.2242(4) 0.0288(10) Uani 1 1 d . . . N2 N 0.6060(6) 0.7469(5) 0.1204(5) 0.0361(12) Uani 1 1 d . . . N3 N 0.7469(7) 0.5847(6) 0.3380(5) 0.0418(14) Uani 1 1 d D . . H19 H 0.734(9) 0.504(4) 0.396(5) 0.050 Uiso 1 1 d D . . H20 H 0.693(8) 0.570(8) 0.289(6) 0.050 Uiso 1 1 d D . . N4 N 0.8506(6) 0.5648(5) 0.1352(4) 0.0340(12) Uani 1 1 d . . . O1 O 0.2960(7) 0.3393(5) 0.2240(4) 0.0559(15) Uani 1 1 d . . . O2 O 0.3484(5) 0.1972(4) 0.4180(4) 0.0320(9) Uani 1 1 d . . . C21 C 0.9986(13) -0.0029(12) 0.1085(8) 0.129(7) Uani 1 1 d D . . C22 C 0.9024(11) 0.0938(10) 0.0171(13) 0.154(10) Uani 1 1 d D . . H22 H 0.8370 0.1563 0.0319 0.185 Uiso 1 1 calc R . . C23 C 0.9058(12) 0.0951(10) -0.0889(13) 0.135(8) Uani 1 1 d D . . H23 H 0.8427 0.1592 -0.1515 0.162 Uiso 1 1 calc R . . C24 C 1.003(3) -0.0004(15) 0.2122(15) 0.076(6) Uani 0.50 1 d PD . . H24A H 0.9330 0.0731 0.2123 0.091 Uiso 0.50 1 calc PR . . H24B H 1.1001 0.0129 0.2278 0.091 Uiso 0.50 1 calc PR . . O3 O 0.9705(11) -0.1201(10) 0.2987(9) 0.050(2) Uani 0.50 1 d PD . . H3 H 1.0465 -0.1728 0.3267 0.075 Uiso 0.50 1 calc PRD . . 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 0.030(3) 0.043(3) 0.043(3) -0.015(3) -0.001(3) -0.002(3) C2 0.042(4) 0.040(3) 0.050(4) -0.011(3) -0.003(3) -0.002(3) C3 0.057(5) 0.037(4) 0.085(6) -0.027(4) 0.026(5) -0.001(3) C4 0.061(6) 0.060(5) 0.095(7) -0.049(5) 0.013(5) -0.009(4) C5 0.127(9) 0.077(6) 0.044(4) -0.043(4) 0.030(5) -0.050(6) C6 0.061(6) 0.074(5) 0.067(5) -0.036(5) -0.004(4) -0.022(4) C7 0.033(4) 0.064(4) 0.047(4) -0.030(3) -0.011(3) 0.011(3) C8 0.047(4) 0.037(3) 0.047(4) -0.024(3) -0.002(3) 0.002(3) C9 0.048(4) 0.041(3) 0.032(3) -0.018(3) 0.004(3) 0.001(3) C10 0.039(4) 0.052(4) 0.034(3) -0.028(3) 0.009(3) -0.006(3) C11 0.037(4) 0.026(3) 0.033(3) -0.007(2) 0.004(3) -0.006(2) C12 0.040(4) 0.038(3) 0.031(3) -0.010(3) 0.003(3) -0.005(3) C13 0.038(4) 0.040(3) 0.028(3) -0.017(2) 0.007(2) -0.018(3) C14 0.039(4) 0.046(3) 0.034(3) -0.021(3) 0.009(3) -0.017(3) C15 0.034(4) 0.029(3) 0.054(4) -0.014(3) -0.009(3) -0.007(3) C16 0.073(7) 0.070(6) 0.136(10) -0.076(7) 0.020(7) -0.025(5) C17 0.056(5) 0.043(4) 0.083(6) 0.017(4) -0.035(5) -0.026(4) C18 0.033(4) 0.042(4) 0.059(4) -0.008(3) 0.001(3) -0.007(3) Br1 0.0999(10) 0.0694(7) 0.0750(7) -0.0143(5) -0.0306(6) -0.0118(6) N1 0.032(3) 0.030(2) 0.027(2) -0.0154(19) 0.008(2) -0.007(2) N2 0.026(3) 0.034(2) 0.039(3) -0.010(2) 0.002(2) 0.003(2) N3 0.047(4) 0.050(3) 0.038(3) -0.024(3) 0.002(3) -0.020(3) N4 0.036(3) 0.034(2) 0.031(2) -0.014(2) -0.006(2) 0.001(2) O1 0.071(4) 0.067(3) 0.031(2) -0.014(2) -0.006(2) -0.038(3) O2 0.031(2) 0.0283(19) 0.036(2) -0.0115(16) 0.0016(18) -0.0126(17) C21 0.080(9) 0.076(8) 0.178(15) 0.008(9) -0.037(10) -0.064(7) C22 0.072(9) 0.070(7) 0.218(19) 0.040(10) -0.076(12) -0.039(6) C23 0.054(7) 0.051(6) 0.214(18) 0.027(8) -0.058(10) -0.029(5) C24 0.080(15) 0.046(9) 0.111(17) -0.042(11) 0.044(13) -0.029(9) O3 0.037(6) 0.055(6) 0.053(6) -0.020(5) 0.015(5) -0.014(5) _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 1.485(8) . ? C1 C2 1.534(10) . ? C2 N2 1.494(10) . ? C3 C4 1.392(14) . ? C3 N2 1.419(10) . ? C4 C5 1.450(13) . ? C5 N3 1.576(12) . ? C6 N3 1.458(11) . ? C6 C7 1.533(12) . ? C7 N4 1.462(8) . ? C8 N4 1.456(8) . ? C8 C9 1.483(10) . ? C9 C10 1.514(10) . ? C10 N1 1.457(8) . ? C11 N2 1.460(8) . ? C11 C12 1.530(10) . ? C12 N4 1.452(8) . ? C13 N1 1.451(7) . ? C13 C14 1.522(9) . ? C14 O1 1.205(8) . ? C14 O2 1.339(7) . ? C15 O2 1.486(7) . ? C15 C17 1.487(10) . ? C15 C18 1.490(10) . ? C15 C16 1.526(13) . ? C21 C24 1.316(16) . ? C21 C23 1.384(14) 2_755 ? C21 C22 1.419(12) . ? C22 C23 1.321(15) . ? C23 C21 1.384(14) 2_755 ? C24 O3 1.376(14) . ? 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 110.9(6) . . ? N2 C2 C1 112.7(6) . . ? C4 C3 N2 112.5(8) . . ? C3 C4 C5 115.1(8) . . ? C4 C5 N3 115.6(7) . . ? N3 C6 C7 112.2(7) . . ? N4 C7 C6 110.9(6) . . ? N4 C8 C9 112.1(6) . . ? C8 C9 C10 113.0(6) . . ? N1 C10 C9 114.9(5) . . ? N2 C11 C12 112.7(5) . . ? N4 C12 C11 113.0(5) . . ? N1 C13 C14 114.9(5) . . ? O1 C14 O2 125.1(6) . . ? O1 C14 C13 125.1(6) . . ? O2 C14 C13 109.7(5) . . ? O2 C15 C17 102.6(5) . . ? O2 C15 C18 111.4(5) . . ? C17 C15 C18 112.0(7) . . ? O2 C15 C16 107.7(6) . . ? C17 C15 C16 111.1(8) . . ? C18 C15 C16 111.6(7) . . ? C13 N1 C10 112.7(5) . . ? C13 N1 C1 112.6(5) . . ? C10 N1 C1 114.7(5) . . ? C3 N2 C11 115.3(6) . . ? C3 N2 C2 113.3(7) . . ? C11 N2 C2 111.7(5) . . ? C6 N3 C5 113.0(6) . . ? C12 N4 C8 116.2(5) . . ? C12 N4 C7 116.0(6) . . ? C8 N4 C7 112.3(5) . . ? C14 O2 C15 121.1(5) . . ? C24 C21 C23 118.9(16) . 2_755 ? C24 C21 C22 119.4(17) . . ? C23 C21 C22 121.5(8) 2_755 . ? C23 C22 C21 118.6(8) . . ? C22 C23 C21 119.9(7) . 2_755 ? C21 C24 O3 107.4(12) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 N2 -58.9(8) . . . . ? N2 C3 C4 C5 -60.6(11) . . . . ? C3 C4 C5 N3 65.4(12) . . . . ? N3 C6 C7 N4 41.0(9) . . . . ? N4 C8 C9 C10 67.6(7) . . . . ? C8 C9 C10 N1 -96.7(7) . . . . ? N2 C11 C12 N4 -40.6(8) . . . . ? N1 C13 C14 O1 -21.8(11) . . . . ? N1 C13 C14 O2 160.0(5) . . . . ? C14 C13 N1 C10 -60.3(8) . . . . ? C14 C13 N1 C1 71.4(7) . . . . ? C9 C10 N1 C13 -86.2(7) . . . . ? C9 C10 N1 C1 143.1(6) . . . . ? C2 C1 N1 C13 161.3(6) . . . . ? C2 C1 N1 C10 -68.0(7) . . . . ? C4 C3 N2 C11 -74.3(9) . . . . ? C4 C3 N2 C2 155.3(7) . . . . ? C12 C11 N2 C3 160.5(7) . . . . ? C12 C11 N2 C2 -68.2(7) . . . . ? C1 C2 N2 C3 -77.9(8) . . . . ? C1 C2 N2 C11 149.9(6) . . . . ? C7 C6 N3 C5 -152.7(7) . . . . ? C4 C5 N3 C6 62.1(10) . . . . ? C11 C12 N4 C8 144.4(6) . . . . ? C11 C12 N4 C7 -80.2(7) . . . . ? C9 C8 N4 C12 -126.2(6) . . . . ? C9 C8 N4 C7 96.9(7) . . . . ? C6 C7 N4 C12 83.5(8) . . . . ? C6 C7 N4 C8 -139.5(7) . . . . ? O1 C14 O2 C15 5.5(11) . . . . ? C13 C14 O2 C15 -176.3(6) . . . . ? C17 C15 O2 C14 178.1(7) . . . . ? C18 C15 O2 C14 -61.9(8) . . . . ? C16 C15 O2 C14 60.9(8) . . . . ? C24 C21 C22 C23 175.7(13) . . . . ? C23 C21 C22 C23 -0.3(19) 2_755 . . . ? C21 C22 C23 C21 0.3(19) . . . 2_755 ? C23 C21 C24 O3 -63(2) 2_755 . . . ? C22 C21 C24 O3 120.9(14) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.484 _refine_diff_density_min -1.312 _refine_diff_density_rms 0.151 # Attachment '- compound 4.cif' data_sja41_06 _database_code_depnum_ccdc_archive 'CCDC 803780' #TrackingRef '- compound 4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H36 I2 N4 O2' _chemical_formula_weight 618.33 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' I I -0.4742 1.8119 '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 orthorhombic _symmetry_space_group_name_H-M Pca21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y, z+1/2' 'x+1/2, -y, z' _cell_length_a 16.4087(6) _cell_length_b 10.9231(7) _cell_length_c 13.3642(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2395.3(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 36612 _cell_measurement_theta_min 2.71 _cell_measurement_theta_max 34.66 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.715 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1224 _exptl_absorpt_coefficient_mu 2.648 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.0934 _exptl_absorpt_correction_T_max 0.2506 _exptl_absorpt_process_details 'X-RED (Stoe & Cie, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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-II image plate' _diffrn_measurement_method '\w scans, 165 frames at 1\% intervals, exposure time 1 minute' _diffrn_reflns_number 28802 _diffrn_reflns_av_R_equivalents 0.0644 _diffrn_reflns_av_sigmaI/netI 0.0472 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.71 _diffrn_reflns_theta_max 34.83 _reflns_number_total 10134 _reflns_number_gt 7973 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'X-AREA (Stoe & Cie, 2002)' _computing_cell_refinement X-AREA _computing_data_reduction 'X-RED (Stoe & Cie, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP III (Farrugia, 1997)' _computing_publication_material 'WinGX (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^)+(0.0867P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0120(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.03(3) _refine_ls_number_reflns 10134 _refine_ls_number_parameters 255 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0630 _refine_ls_R_factor_gt 0.0496 _refine_ls_wR_factor_ref 0.1373 _refine_ls_wR_factor_gt 0.1273 _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 N1 N 0.4511(2) 0.1168(3) 0.2315(3) 0.0261(6) Uani 1 1 d . . . N2 N 0.6136(2) 0.2089(4) 0.1858(3) 0.0276(6) Uani 1 1 d . . . N3 N 0.5732(3) 0.4151(4) 0.2286(3) 0.0310(8) Uani 1 1 d . . . N4 N 0.4523(3) 0.2836(4) 0.1111(3) 0.0309(7) Uani 1 1 d . . . C1 C 0.5107(3) 0.0423(4) 0.1710(3) 0.0299(8) Uani 1 1 d . . . H1A H 0.5023 -0.0458 0.1848 0.036 Uiso 1 1 calc R . . H1B H 0.5009 0.0564 0.0988 0.036 Uiso 1 1 calc R . . C2 C 0.5972(3) 0.0771(5) 0.1963(4) 0.0320(9) Uani 1 1 d . . . H2A H 0.6088 0.0521 0.2661 0.038 Uiso 1 1 calc R . . H2B H 0.6347 0.0312 0.1520 0.038 Uiso 1 1 calc R . . C3 C 0.6985(3) 0.2304(6) 0.2160(5) 0.0399(11) Uani 1 1 d . . . H3A H 0.7352 0.1784 0.1754 0.048 Uiso 1 1 calc R . . H3B H 0.7055 0.2076 0.2872 0.048 Uiso 1 1 calc R . . C4 C 0.7209(3) 0.3633(6) 0.2018(4) 0.0404(11) Uani 1 1 d . . . H4A H 0.7765 0.3781 0.2278 0.048 Uiso 1 1 calc R . . H4B H 0.7203 0.3837 0.1296 0.048 Uiso 1 1 calc R . . C5 C 0.6611(3) 0.4426(5) 0.2564(4) 0.0393(11) Uani 1 1 d . . . H5A H 0.6730 0.5295 0.2412 0.047 Uiso 1 1 calc R . . H5B H 0.6682 0.4306 0.3293 0.047 Uiso 1 1 calc R . . C6 C 0.5568(4) 0.4447(5) 0.1200(4) 0.0377(10) Uani 1 1 d . . . H6A H 0.5661 0.5331 0.1083 0.045 Uiso 1 1 calc R . . H6B H 0.5951 0.3983 0.0771 0.045 Uiso 1 1 calc R . . C7 C 0.4712(4) 0.4128(5) 0.0923(5) 0.0408(11) Uani 1 1 d . . . H7A H 0.4332 0.4646 0.1312 0.049 Uiso 1 1 calc R . . H7B H 0.4626 0.4308 0.0204 0.049 Uiso 1 1 calc R . . C8 C 0.3667(4) 0.2640(6) 0.0835(5) 0.0444(13) Uani 1 1 d . . . H8A H 0.3575 0.2910 0.0137 0.053 Uiso 1 1 calc R . . H8B H 0.3310 0.3132 0.1277 0.053 Uiso 1 1 calc R . . C9 C 0.3458(4) 0.1306(6) 0.0935(4) 0.0392(11) Uani 1 1 d . . . H9A H 0.3778 0.0824 0.0447 0.047 Uiso 1 1 calc R . . H9B H 0.2872 0.1182 0.0788 0.047 Uiso 1 1 calc R . . C10 C 0.3645(3) 0.0867(5) 0.1990(3) 0.0326(9) Uani 1 1 d . . . H10A H 0.3564 -0.0030 0.2023 0.039 Uiso 1 1 calc R . . H10B H 0.3257 0.1253 0.2462 0.039 Uiso 1 1 calc R . . C11 C 0.4668(3) 0.2534(4) 0.2145(3) 0.0258(7) Uani 1 1 d . . . H11 H 0.4294 0.3024 0.2578 0.031 Uiso 1 1 calc R . . C12 C 0.5566(3) 0.2792(4) 0.2452(3) 0.0247(7) Uani 1 1 d . . . H12 H 0.5642 0.2590 0.3176 0.030 Uiso 1 1 calc R . . C13 C 0.4580(3) 0.0911(4) 0.3455(3) 0.0314(9) Uani 1 1 d . . . H13A H 0.5163 0.0831 0.3632 0.038 Uiso 1 1 calc R . . H13B H 0.4360 0.1623 0.3824 0.038 Uiso 1 1 calc R . . C14 C 0.4140(3) -0.0219(4) 0.3795(3) 0.0278(7) Uani 1 1 d . . . C15 C 0.3360(3) -0.0104(4) 0.4212(4) 0.0343(9) Uani 1 1 d . . . H15 H 0.3123 0.0684 0.4290 0.041 Uiso 1 1 calc R . . C16 C 0.2932(4) -0.1138(5) 0.4513(4) 0.0390(10) Uani 1 1 d . . . H16 H 0.2407 -0.1051 0.4805 0.047 Uiso 1 1 calc R . . C17 C 0.3255(4) -0.2262(5) 0.4396(4) 0.0346(10) Uani 1 1 d . . . H17 H 0.2952 -0.2965 0.4587 0.042 Uiso 1 1 calc R . . C18 C 0.4033(4) -0.2394(5) 0.3994(5) 0.0428(13) Uani 1 1 d . . . H18 H 0.4259 -0.3188 0.3910 0.051 Uiso 1 1 calc R . . C19 C 0.4478(3) -0.1374(5) 0.3716(4) 0.0374(10) Uani 1 1 d . . . H19 H 0.5018 -0.1467 0.3470 0.045 Uiso 1 1 calc R . . C20 C 0.5219(4) 0.4909(5) 0.2973(5) 0.0445(13) Uani 1 1 d . . . H20A H 0.5266 0.4593 0.3657 0.067 Uiso 1 1 calc R . . H20B H 0.4649 0.4871 0.2759 0.067 Uiso 1 1 calc R . . H20C H 0.5407 0.5761 0.2955 0.067 Uiso 1 1 calc R . . O1 O 0.1193(3) 0.2249(5) 0.1187(4) 0.0560(12) Uani 1 1 d . . . H21A H 0.1474 0.2689 0.0684 0.084 Uiso 1 1 d R . . H21B H 0.0661 0.2129 0.0909 0.084 Uiso 1 1 d R . . O2 O 0.1524(5) 0.1938(8) 0.3197(5) 0.092(3) Uani 1 1 d . . . H22A H 0.1872 0.2585 0.3425 0.138 Uiso 1 1 d R . . H22B H 0.1440 0.2106 0.2501 0.138 Uiso 1 1 d R . . I1 I 0.413497(17) 0.74808(3) 0.04674(3) 0.03150(7) Uani 1 1 d . . . I2 I 0.310876(16) 0.39221(3) 0.41153(2) 0.03270(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0312(17) 0.0235(15) 0.0236(14) -0.0027(12) -0.0033(12) -0.0053(13) N2 0.0306(16) 0.0264(16) 0.0258(15) -0.0040(13) -0.0010(13) 0.0007(14) N3 0.038(2) 0.0217(16) 0.0331(18) -0.0060(13) 0.0092(15) -0.0065(14) N4 0.0354(19) 0.0283(16) 0.0289(17) 0.0046(14) -0.0061(14) -0.0003(15) C1 0.037(2) 0.0240(17) 0.0290(18) -0.0015(14) -0.0006(15) 0.0004(16) C2 0.036(2) 0.0270(19) 0.033(2) -0.0022(16) 0.0006(16) 0.0049(16) C3 0.030(2) 0.043(3) 0.047(3) 0.001(2) -0.0014(19) -0.0030(19) C4 0.033(2) 0.048(3) 0.039(2) -0.004(2) -0.0001(18) -0.015(2) C5 0.040(2) 0.039(3) 0.038(2) -0.0079(19) 0.0066(19) -0.015(2) C6 0.048(3) 0.026(2) 0.039(2) 0.0081(17) 0.0064(19) -0.0016(19) C7 0.046(3) 0.034(2) 0.043(3) 0.014(2) -0.003(2) 0.002(2) C8 0.039(3) 0.047(3) 0.047(3) 0.013(2) -0.013(2) 0.001(2) C9 0.037(2) 0.046(3) 0.035(2) 0.000(2) -0.0118(18) -0.008(2) C10 0.034(2) 0.035(2) 0.0295(19) -0.0028(16) -0.0047(15) -0.0088(17) C11 0.0298(18) 0.0220(16) 0.0256(16) -0.0005(13) -0.0016(13) -0.0001(14) C12 0.0308(19) 0.0212(15) 0.0220(15) -0.0027(12) 0.0011(13) -0.0041(14) C13 0.040(2) 0.032(2) 0.0224(16) 0.0014(14) -0.0046(15) -0.0120(18) C14 0.0323(19) 0.0244(18) 0.0266(16) 0.0020(14) 0.0008(14) -0.0044(15) C15 0.041(2) 0.0299(19) 0.032(2) -0.0009(18) 0.0089(19) 0.0011(16) C16 0.038(2) 0.042(3) 0.038(2) 0.007(2) 0.0025(19) -0.009(2) C17 0.046(3) 0.0266(19) 0.0308(19) 0.0053(15) 0.0004(17) -0.0103(18) C18 0.062(4) 0.027(2) 0.040(3) 0.0071(19) 0.013(2) 0.011(2) C19 0.038(2) 0.035(2) 0.039(2) 0.0105(19) 0.0071(18) 0.0104(19) C20 0.051(3) 0.027(2) 0.056(3) -0.016(2) 0.019(3) -0.008(2) O1 0.053(3) 0.064(3) 0.051(3) 0.023(2) -0.009(2) -0.008(2) O2 0.096(5) 0.128(6) 0.053(3) -0.006(4) -0.001(3) -0.077(5) I1 0.03295(13) 0.02945(12) 0.03210(12) 0.00137(10) 0.00104(11) 0.00102(10) I2 0.03010(12) 0.03360(13) 0.03441(12) 0.00005(14) -0.00021(13) 0.00015(10) _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 N1 C1 1.508(6) . ? N1 C10 1.522(6) . ? N1 C11 1.532(5) . ? N1 C13 1.553(6) . ? N2 C12 1.447(6) . ? N2 C3 1.469(7) . ? N2 C2 1.472(6) . ? N3 C20 1.496(6) . ? N3 C6 1.511(7) . ? N3 C5 1.520(7) . ? N3 C12 1.525(6) . ? N4 C11 1.440(6) . ? N4 C7 1.467(7) . ? N4 C8 1.469(8) . ? C1 C2 1.507(7) . ? C3 C4 1.509(9) . ? C4 C5 1.498(8) . ? C6 C7 1.495(8) . ? C8 C9 1.503(8) . ? C9 C10 1.520(7) . ? C11 C12 1.555(6) . ? C13 C14 1.501(6) . ? C14 C19 1.382(7) . ? C14 C15 1.401(6) . ? C15 C16 1.390(7) . ? C16 C17 1.346(8) . ? C17 C18 1.393(9) . ? C18 C19 1.383(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C10 109.7(3) . . ? C1 N1 C11 109.6(3) . . ? C10 N1 C11 109.0(4) . . ? C1 N1 C13 112.4(4) . . ? C10 N1 C13 108.0(4) . . ? C11 N1 C13 108.1(3) . . ? C12 N2 C3 112.1(4) . . ? C12 N2 C2 110.4(4) . . ? C3 N2 C2 107.7(4) . . ? C20 N3 C6 111.8(5) . . ? C20 N3 C5 105.9(4) . . ? C6 N3 C5 111.2(4) . . ? C20 N3 C12 110.4(4) . . ? C6 N3 C12 108.5(3) . . ? C5 N3 C12 109.0(4) . . ? C11 N4 C7 110.5(4) . . ? C11 N4 C8 111.4(4) . . ? C7 N4 C8 107.4(4) . . ? C2 C1 N1 110.8(4) . . ? N2 C2 C1 113.4(4) . . ? N2 C3 C4 110.5(5) . . ? C5 C4 C3 109.6(5) . . ? C4 C5 N3 112.8(4) . . ? C7 C6 N3 110.8(4) . . ? N4 C7 C6 112.4(4) . . ? N4 C8 C9 109.7(4) . . ? C8 C9 C10 110.0(4) . . ? C9 C10 N1 112.6(4) . . ? N4 C11 N1 109.8(3) . . ? N4 C11 C12 111.6(4) . . ? N1 C11 C12 107.3(3) . . ? N2 C12 N3 108.8(3) . . ? N2 C12 C11 111.8(3) . . ? N3 C12 C11 107.9(4) . . ? C14 C13 N1 114.2(3) . . ? C19 C14 C15 118.7(4) . . ? C19 C14 C13 122.3(4) . . ? C15 C14 C13 119.1(4) . . ? C16 C15 C14 120.3(5) . . ? C17 C16 C15 120.5(5) . . ? C16 C17 C18 120.1(5) . . ? C19 C18 C17 120.3(5) . . ? C14 C19 C18 120.1(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C10 N1 C1 C2 175.8(4) . . . . ? C11 N1 C1 C2 56.2(5) . . . . ? C13 N1 C1 C2 -64.0(5) . . . . ? C12 N2 C2 C1 55.3(5) . . . . ? C3 N2 C2 C1 178.0(4) . . . . ? N1 C1 C2 N2 -54.5(5) . . . . ? C12 N2 C3 C4 -61.4(6) . . . . ? C2 N2 C3 C4 177.0(4) . . . . ? N2 C3 C4 C5 54.6(6) . . . . ? C3 C4 C5 N3 -53.2(6) . . . . ? C20 N3 C5 C4 173.7(5) . . . . ? C6 N3 C5 C4 -64.7(6) . . . . ? C12 N3 C5 C4 54.9(6) . . . . ? C20 N3 C6 C7 -64.1(5) . . . . ? C5 N3 C6 C7 177.8(4) . . . . ? C12 N3 C6 C7 57.9(5) . . . . ? C11 N4 C7 C6 56.9(6) . . . . ? C8 N4 C7 C6 178.6(5) . . . . ? N3 C6 C7 N4 -57.2(6) . . . . ? C11 N4 C8 C9 -63.4(6) . . . . ? C7 N4 C8 C9 175.5(5) . . . . ? N4 C8 C9 C10 56.0(7) . . . . ? C8 C9 C10 N1 -52.5(6) . . . . ? C1 N1 C10 C9 -68.0(5) . . . . ? C11 N1 C10 C9 52.1(5) . . . . ? C13 N1 C10 C9 169.2(4) . . . . ? C7 N4 C11 N1 -177.1(4) . . . . ? C8 N4 C11 N1 63.7(5) . . . . ? C7 N4 C11 C12 -58.3(5) . . . . ? C8 N4 C11 C12 -177.6(4) . . . . ? C1 N1 C11 N4 63.3(5) . . . . ? C10 N1 C11 N4 -56.7(5) . . . . ? C13 N1 C11 N4 -173.8(4) . . . . ? C1 N1 C11 C12 -58.1(4) . . . . ? C10 N1 C11 C12 -178.1(3) . . . . ? C13 N1 C11 C12 64.8(4) . . . . ? C3 N2 C12 N3 62.4(5) . . . . ? C2 N2 C12 N3 -177.5(4) . . . . ? C3 N2 C12 C11 -178.6(4) . . . . ? C2 N2 C12 C11 -58.5(5) . . . . ? C20 N3 C12 N2 -173.6(4) . . . . ? C6 N3 C12 N2 63.5(5) . . . . ? C5 N3 C12 N2 -57.7(5) . . . . ? C20 N3 C12 C11 65.0(5) . . . . ? C6 N3 C12 C11 -57.9(4) . . . . ? C5 N3 C12 C11 -179.1(4) . . . . ? N4 C11 C12 N2 -59.8(5) . . . . ? N1 C11 C12 N2 60.5(4) . . . . ? N4 C11 C12 N3 59.7(4) . . . . ? N1 C11 C12 N3 180.0(3) . . . . ? C1 N1 C13 C14 -81.4(5) . . . . ? C10 N1 C13 C14 39.7(5) . . . . ? C11 N1 C13 C14 157.4(4) . . . . ? N1 C13 C14 C19 82.6(6) . . . . ? N1 C13 C14 C15 -97.8(5) . . . . ? C19 C14 C15 C16 -1.8(8) . . . . ? C13 C14 C15 C16 178.6(5) . . . . ? C14 C15 C16 C17 -0.9(9) . . . . ? C15 C16 C17 C18 1.7(9) . . . . ? C16 C17 C18 C19 0.1(10) . . . . ? C15 C14 C19 C18 3.6(8) . . . . ? C13 C14 C19 C18 -176.8(5) . . . . ? C17 C18 C19 C14 -2.8(9) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 34.83 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 2.049 _refine_diff_density_min -1.681 _refine_diff_density_rms 0.214 data_sja51_06 _database_code_depnum_ccdc_archive 'CCDC 803781' #TrackingRef '- compound 6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20.50 H38 Cl2 N4 O8.50' _chemical_formula_weight 547.45 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 17.4472(18) _cell_length_b 11.3606(12) _cell_length_c 15.194(2) _cell_angle_alpha 90.00 _cell_angle_beta 101.430(10) _cell_angle_gamma 90.00 _cell_volume 2951.9(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 13382 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 30.97 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.232 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1164 _exptl_absorpt_coefficient_mu 0.267 _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 150(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-II image plate' _diffrn_measurement_method '\w scans, 136 frames at 2\% intervals, exposure time 3 minutes' _diffrn_reflns_number 62025 _diffrn_reflns_av_R_equivalents 0.1142 _diffrn_reflns_av_sigmaI/netI 0.1488 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.38 _diffrn_reflns_theta_max 34.84 _reflns_number_total 12678 _reflns_number_gt 3475 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'X-AREA (Stoe & Cie, 2002)' _computing_cell_refinement X-AREA _computing_data_reduction 'X-RED (Stoe & Cie, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP III (Farrugia, 1997)' _computing_publication_material 'WinGX (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^)+(0.1659P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.011(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 12678 _refine_ls_number_parameters 332 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.2549 _refine_ls_R_factor_gt 0.1161 _refine_ls_wR_factor_ref 0.3692 _refine_ls_wR_factor_gt 0.3265 _refine_ls_goodness_of_fit_ref 0.990 _refine_ls_restrained_S_all 0.991 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.3135(2) 0.5907(4) 0.5602(3) 0.0454(9) Uani 1 1 d . . . H1A H 0.3333 0.6141 0.6234 0.054 Uiso 1 1 calc R . . H1B H 0.3454 0.5234 0.5467 0.054 Uiso 1 1 calc R . . C2 C 0.2294(3) 0.5522(4) 0.5493(3) 0.0504(10) Uani 1 1 d . . . H2A H 0.2133 0.5150 0.4895 0.060 Uiso 1 1 calc R . . H2B H 0.2260 0.4915 0.5950 0.060 Uiso 1 1 calc R . . C3 C 0.0948(3) 0.5961(5) 0.5359(3) 0.0618(13) Uani 1 1 d . . . H3A H 0.0870 0.5441 0.5857 0.074 Uiso 1 1 calc R . . H3B H 0.0899 0.5472 0.4811 0.074 Uiso 1 1 calc R . . C4 C 0.0298(3) 0.6915(6) 0.5204(4) 0.0714(16) Uani 1 1 d . . . H4A H -0.0218 0.6522 0.5099 0.086 Uiso 1 1 calc R . . H4B H 0.0344 0.7397 0.5755 0.086 Uiso 1 1 calc R . . C5 C 0.0336(2) 0.7717(5) 0.4419(3) 0.0618(13) Uani 1 1 d . . . H5A H 0.0242 0.7250 0.3858 0.074 Uiso 1 1 calc R . . H5B H -0.0081 0.8317 0.4368 0.074 Uiso 1 1 calc R . . C6 C 0.1212(3) 0.9255(5) 0.5229(3) 0.0548(11) Uani 1 1 d . . . H6A H 0.1017 0.8958 0.5757 0.066 Uiso 1 1 calc R . . H6B H 0.0890 0.9945 0.4990 0.066 Uiso 1 1 calc R . . C7 C 0.2056(3) 0.9639(4) 0.5526(3) 0.0552(11) Uani 1 1 d . . . H7A H 0.2221 1.0051 0.5020 0.066 Uiso 1 1 calc R . . H7B H 0.2088 1.0210 0.6024 0.066 Uiso 1 1 calc R . . C8 C 0.3406(2) 0.9178(4) 0.6009(3) 0.0490(10) Uani 1 1 d . . . H8A H 0.3476 0.9651 0.6567 0.059 Uiso 1 1 calc R . . H8B H 0.3460 0.9715 0.5512 0.059 Uiso 1 1 calc R . . C9 C 0.4053(2) 0.8240(4) 0.6112(3) 0.0481(10) Uani 1 1 d . . . H9A H 0.4569 0.8635 0.6258 0.058 Uiso 1 1 calc R . . H9B H 0.4008 0.7718 0.6620 0.058 Uiso 1 1 calc R . . C10 C 0.4017(2) 0.7502(4) 0.5279(3) 0.0448(9) Uani 1 1 d . . . H10A H 0.4432 0.6894 0.5395 0.054 Uiso 1 1 calc R . . H10B H 0.4117 0.8007 0.4783 0.054 Uiso 1 1 calc R . . C11 C 0.1874(2) 0.7024(4) 0.6474(3) 0.0506(10) Uani 1 1 d . . . H11A H 0.2063 0.6410 0.6927 0.061 Uiso 1 1 calc R . . H11B H 0.1365 0.7306 0.6584 0.061 Uiso 1 1 calc R . . C12 C 0.2452(2) 0.8056(4) 0.6635(3) 0.0491(10) Uani 1 1 d . . . H12A H 0.2250 0.8644 0.7013 0.059 Uiso 1 1 calc R . . H12B H 0.2955 0.7760 0.6983 0.059 Uiso 1 1 calc R . . C13 C 0.3030(2) 0.6625(4) 0.4010(2) 0.0373(8) Uani 1 1 d . . . H13A H 0.2476 0.6378 0.3856 0.045 Uiso 1 1 calc R . . H13B H 0.3085 0.7349 0.3666 0.045 Uiso 1 1 calc R . . C14 C 0.3527(2) 0.5674(4) 0.3719(3) 0.0411(9) Uani 1 1 d . . . C15 C 0.4259(2) 0.5945(4) 0.3534(3) 0.0479(10) Uani 1 1 d . . . H15 H 0.4457 0.6724 0.3621 0.058 Uiso 1 1 calc R . . C16 C 0.4695(3) 0.5084(6) 0.3225(3) 0.0638(14) Uani 1 1 d . . . H16 H 0.5194 0.5271 0.3103 0.077 Uiso 1 1 calc R . . C17 C 0.4415(3) 0.3976(5) 0.3093(3) 0.0672(15) Uani 1 1 d . . . H17 H 0.4720 0.3387 0.2881 0.081 Uiso 1 1 calc R . . C18 C 0.3685(4) 0.3692(5) 0.3267(4) 0.0677(14) Uani 1 1 d . . . H18 H 0.3488 0.2912 0.3174 0.081 Uiso 1 1 calc R . . C19 C 0.3250(3) 0.4549(4) 0.3575(3) 0.0518(11) Uani 1 1 d . . . H19 H 0.2748 0.4359 0.3690 0.062 Uiso 1 1 calc R . . C20 C 0.1247(3) 0.8778(5) 0.3646(3) 0.0636(13) Uani 1 1 d . . . H20A H 0.1179 0.8138 0.3205 0.095 Uiso 1 1 calc R . . H20B H 0.1779 0.9091 0.3722 0.095 Uiso 1 1 calc R . . H20C H 0.0870 0.9406 0.3435 0.095 Uiso 1 1 calc R . . N1 N 0.32308(17) 0.6911(3) 0.5001(2) 0.0383(7) Uani 1 1 d D . . H21 H 0.287(2) 0.747(3) 0.507(3) 0.057 Uiso 1 1 d D . . N2 N 0.17379(19) 0.6463(4) 0.5574(2) 0.0485(9) Uani 1 1 d . . . N3 N 0.11134(19) 0.8318(4) 0.4528(2) 0.0509(9) Uani 1 1 d D . . H22 H 0.147(3) 0.771(4) 0.475(4) 0.076 Uiso 1 1 d D . . N4 N 0.26099(18) 0.8667(3) 0.5826(2) 0.0411(7) Uani 1 1 d . . . Cl1 Cl 0.37006(7) 0.98848(10) 0.32823(7) 0.0514(3) Uani 1 1 d . . . Cl2 Cl -0.06578(7) 1.02917(13) 0.23504(9) 0.0644(4) Uani 1 1 d . . . O1 O 0.3576(4) 1.0694(4) 0.2580(4) 0.1138(19) Uani 1 1 d . . . O2 O 0.4256(4) 1.0358(7) 0.3967(4) 0.150(3) Uani 1 1 d . . . O3 O 0.3944(3) 0.8818(3) 0.2941(3) 0.0897(14) Uani 1 1 d . . . O4 O 0.3042(3) 0.9641(5) 0.3653(4) 0.1044(16) Uani 1 1 d . . . O5 O -0.0091(3) 0.9931(6) 0.1914(3) 0.121(2) Uani 1 1 d . . . O6 O -0.0815(4) 0.9510(5) 0.3002(3) 0.1178(19) Uani 1 1 d . . . O7 O -0.0303(4) 1.1269(7) 0.2922(5) 0.150(3) Uani 1 1 d . . . O8 O -0.1278(3) 1.0802(6) 0.1818(4) 0.125(2) Uani 1 1 d . . . O9 O 0.3798(5) 1.2473(7) 0.5650(7) 0.094(3) Uani 0.50 1 d PD . . C21 C 0.2995(7) 1.2568(13) 0.5461(16) 0.135(8) Uani 0.50 1 d PD . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.057(2) 0.045(2) 0.036(2) 0.0048(18) 0.0128(17) 0.0046(18) C2 0.061(2) 0.045(2) 0.048(2) 0.005(2) 0.019(2) -0.0039(19) C3 0.058(3) 0.083(4) 0.050(3) -0.005(3) 0.022(2) -0.025(2) C4 0.043(2) 0.117(5) 0.059(3) -0.015(3) 0.022(2) -0.017(3) C5 0.041(2) 0.089(4) 0.055(3) -0.011(3) 0.0086(19) 0.000(2) C6 0.051(2) 0.063(3) 0.051(3) -0.009(2) 0.0109(19) 0.014(2) C7 0.057(2) 0.056(3) 0.052(3) -0.010(2) 0.008(2) 0.013(2) C8 0.052(2) 0.050(2) 0.045(2) -0.008(2) 0.0084(18) -0.0070(19) C9 0.0426(19) 0.056(3) 0.044(2) -0.006(2) 0.0056(17) -0.0023(18) C10 0.0392(18) 0.053(2) 0.042(2) 0.0012(19) 0.0073(16) 0.0034(16) C11 0.050(2) 0.069(3) 0.035(2) 0.000(2) 0.0162(17) -0.001(2) C12 0.049(2) 0.066(3) 0.033(2) -0.007(2) 0.0099(17) 0.004(2) C13 0.0394(17) 0.043(2) 0.0299(18) 0.0015(16) 0.0074(14) 0.0077(15) C14 0.0441(19) 0.050(2) 0.0292(18) 0.0007(17) 0.0076(15) 0.0096(17) C15 0.0423(19) 0.062(3) 0.039(2) 0.000(2) 0.0065(16) 0.0089(18) C16 0.046(2) 0.100(4) 0.044(2) -0.006(3) 0.0052(19) 0.028(3) C17 0.072(3) 0.081(4) 0.045(3) -0.011(3) 0.001(2) 0.040(3) C18 0.100(4) 0.052(3) 0.049(3) -0.004(2) 0.011(3) 0.020(3) C19 0.070(3) 0.045(2) 0.043(2) 0.003(2) 0.016(2) 0.007(2) C20 0.060(3) 0.089(4) 0.043(3) 0.001(3) 0.013(2) 0.004(3) N1 0.0378(14) 0.0427(18) 0.0349(17) 0.0026(14) 0.0086(12) 0.0030(13) N2 0.0458(17) 0.065(2) 0.0380(18) -0.0048(17) 0.0167(14) -0.0132(16) N3 0.0406(17) 0.075(3) 0.0385(19) -0.0035(18) 0.0106(14) 0.0064(16) N4 0.0414(15) 0.0465(19) 0.0354(17) -0.0058(15) 0.0078(13) 0.0016(14) Cl1 0.0627(6) 0.0511(6) 0.0441(6) -0.0052(5) 0.0195(5) -0.0146(5) Cl2 0.0511(6) 0.0895(10) 0.0544(7) 0.0129(7) 0.0148(5) 0.0246(6) O1 0.198(6) 0.068(3) 0.094(4) 0.033(3) 0.074(4) 0.045(3) O2 0.134(5) 0.218(7) 0.091(4) -0.041(4) 0.009(3) -0.108(5) O3 0.139(4) 0.056(2) 0.090(3) 0.004(2) 0.060(3) 0.006(2) O4 0.085(3) 0.118(4) 0.125(4) 0.018(3) 0.057(3) 0.000(3) O5 0.089(3) 0.219(6) 0.059(2) 0.010(3) 0.027(2) 0.090(4) O6 0.185(5) 0.113(4) 0.071(3) 0.017(3) 0.064(3) 0.040(4) O7 0.123(4) 0.194(7) 0.144(5) -0.094(5) 0.053(4) -0.057(4) O8 0.074(3) 0.207(6) 0.100(4) 0.057(4) 0.029(3) 0.075(3) O9 0.106(6) 0.051(4) 0.123(8) 0.009(5) 0.021(6) 0.000(4) C21 0.059(7) 0.085(9) 0.25(2) 0.075(12) 0.020(9) -0.027(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.491(5) . ? C1 C2 1.508(6) . ? C2 N2 1.465(6) . ? C3 N2 1.468(5) . ? C3 C4 1.551(8) . ? C4 C5 1.513(8) . ? C5 N3 1.498(6) . ? C6 N3 1.492(6) . ? C6 C7 1.518(6) . ? C7 N4 1.479(6) . ? C8 N4 1.481(5) . ? C8 C9 1.538(6) . ? C9 C10 1.508(6) . ? C10 N1 1.510(5) . ? C11 N2 1.484(5) . ? C11 C12 1.533(6) . ? C12 N4 1.485(5) . ? C13 C14 1.505(5) . ? C13 N1 1.512(5) . ? C14 C19 1.368(6) . ? C14 C15 1.397(6) . ? C15 C16 1.377(6) . ? C16 C17 1.350(8) . ? C17 C18 1.391(8) . ? C18 C19 1.373(7) . ? C20 N3 1.498(6) . ? Cl1 O2 1.383(5) . ? Cl1 O1 1.393(5) . ? Cl1 O4 1.404(4) . ? Cl1 O3 1.416(4) . ? Cl2 O8 1.347(4) . ? Cl2 O5 1.359(4) . ? Cl2 O6 1.398(5) . ? Cl2 O7 1.469(6) . ? O9 C21 1.378(12) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 112.3(3) . . ? N2 C2 C1 115.2(4) . . ? N2 C3 C4 112.8(4) . . ? C5 C4 C3 113.3(4) . . ? N3 C5 C4 111.6(4) . . ? N3 C6 C7 112.6(3) . . ? N4 C7 C6 114.4(4) . . ? N4 C8 C9 112.9(4) . . ? C10 C9 C8 113.1(4) . . ? C9 C10 N1 111.5(3) . . ? N2 C11 C12 117.1(3) . . ? N4 C12 C11 116.7(3) . . ? C14 C13 N1 114.4(3) . . ? C19 C14 C15 118.8(4) . . ? C19 C14 C13 120.8(4) . . ? C15 C14 C13 120.2(4) . . ? C16 C15 C14 120.1(5) . . ? C17 C16 C15 120.3(5) . . ? C16 C17 C18 120.4(5) . . ? C19 C18 C17 119.3(5) . . ? C14 C19 C18 121.1(5) . . ? C1 N1 C10 112.0(3) . . ? C1 N1 C13 114.4(3) . . ? C10 N1 C13 113.1(3) . . ? C2 N2 C3 107.8(4) . . ? C2 N2 C11 113.8(4) . . ? C3 N2 C11 110.1(3) . . ? C6 N3 C5 112.1(3) . . ? C6 N3 C20 111.9(4) . . ? C5 N3 C20 111.0(4) . . ? C7 N4 C8 107.2(3) . . ? C7 N4 C12 112.8(3) . . ? C8 N4 C12 110.4(3) . . ? O2 Cl1 O1 107.4(4) . . ? O2 Cl1 O4 106.4(4) . . ? O1 Cl1 O4 114.9(3) . . ? O2 Cl1 O3 113.1(4) . . ? O1 Cl1 O3 107.3(3) . . ? O4 Cl1 O3 107.9(3) . . ? O8 Cl2 O5 114.4(3) . . ? O8 Cl2 O6 116.9(4) . . ? O5 Cl2 O6 114.7(3) . . ? O8 Cl2 O7 102.9(5) . . ? O5 Cl2 O7 104.7(4) . . ? O6 Cl2 O7 100.4(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 N2 -52.3(5) . . . . ? N2 C3 C4 C5 62.0(6) . . . . ? C3 C4 C5 N3 -57.3(6) . . . . ? N3 C6 C7 N4 -53.8(6) . . . . ? N4 C8 C9 C10 61.0(5) . . . . ? C8 C9 C10 N1 -56.5(5) . . . . ? N2 C11 C12 N4 20.6(6) . . . . ? N1 C13 C14 C19 101.3(4) . . . . ? N1 C13 C14 C15 -83.0(5) . . . . ? C19 C14 C15 C16 -1.0(6) . . . . ? C13 C14 C15 C16 -176.7(4) . . . . ? C14 C15 C16 C17 0.4(7) . . . . ? C15 C16 C17 C18 0.1(8) . . . . ? C16 C17 C18 C19 -0.1(8) . . . . ? C15 C14 C19 C18 1.0(7) . . . . ? C13 C14 C19 C18 176.8(4) . . . . ? C17 C18 C19 C14 -0.5(7) . . . . ? C2 C1 N1 C10 164.6(3) . . . . ? C2 C1 N1 C13 -65.0(4) . . . . ? C9 C10 N1 C1 -74.3(4) . . . . ? C9 C10 N1 C13 154.7(3) . . . . ? C14 C13 N1 C1 -61.2(4) . . . . ? C14 C13 N1 C10 68.6(4) . . . . ? C1 C2 N2 C3 174.2(4) . . . . ? C1 C2 N2 C11 -63.3(5) . . . . ? C4 C3 N2 C2 -166.7(4) . . . . ? C4 C3 N2 C11 68.6(5) . . . . ? C12 C11 N2 C2 87.4(5) . . . . ? C12 C11 N2 C3 -151.5(4) . . . . ? C7 C6 N3 C5 164.5(4) . . . . ? C7 C6 N3 C20 -70.0(5) . . . . ? C4 C5 N3 C6 -72.8(5) . . . . ? C4 C5 N3 C20 161.2(4) . . . . ? C6 C7 N4 C8 174.9(4) . . . . ? C6 C7 N4 C12 -63.3(5) . . . . ? C9 C8 N4 C7 -166.5(4) . . . . ? C9 C8 N4 C12 70.3(4) . . . . ? C11 C12 N4 C7 88.6(5) . . . . ? C11 C12 N4 C8 -151.5(4) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.612 _refine_diff_density_min -0.536 _refine_diff_density_rms 0.159 # Attachment '- compound [Cu6][(ClO4)2.cif' data_sja70_06 _database_code_depnum_ccdc_archive 'CCDC 803782' #TrackingRef '- compound [Cu6][(ClO4)2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H36 Cl2 Cu N4 O9' _chemical_formula_weight 610.97 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' 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pca21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y, z+1/2' 'x+1/2, -y, z' _cell_length_a 15.571(2) _cell_length_b 9.7171(9) _cell_length_c 16.678(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2523.5(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 11505 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 29.04 _exptl_crystal_description block _exptl_crystal_colour 'blue green' _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.608 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1276 _exptl_absorpt_coefficient_mu 1.135 _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 150(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-II image plate' _diffrn_measurement_method '\w scans, 149 frames at 2\% intervals, exposure time 3 minutes' _diffrn_reflns_number 57231 _diffrn_reflns_av_R_equivalents 0.1636 _diffrn_reflns_av_sigmaI/netI 0.2086 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.44 _diffrn_reflns_theta_max 34.83 _reflns_number_total 10817 _reflns_number_gt 3493 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'X-AREA (Stoe & Cie, 2002)' _computing_cell_refinement X-AREA _computing_data_reduction 'X-RED (Stoe & Cie, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP III (Farrugia, 1997)' _computing_publication_material 'WinGX (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^)+(0.0433P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.003(13) _refine_ls_number_reflns 10817 _refine_ls_number_parameters 325 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1941 _refine_ls_R_factor_gt 0.0453 _refine_ls_wR_factor_ref 0.1152 _refine_ls_wR_factor_gt 0.0873 _refine_ls_goodness_of_fit_ref 0.716 _refine_ls_restrained_S_all 0.716 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.0074(3) 0.5448(5) 0.1871(2) 0.0343(10) Uani 1 1 d . . . H1A H -0.0159 0.5672 0.1297 0.041 Uiso 1 1 calc R . . H1B H -0.0602 0.4992 0.2067 0.041 Uiso 1 1 calc R . . C2 C 0.0669(3) 0.4473(4) 0.1952(2) 0.0309(10) Uani 1 1 d . . . H2A H 0.0708 0.4153 0.2514 0.037 Uiso 1 1 calc R . . H2B H 0.0569 0.3660 0.1607 0.037 Uiso 1 1 calc R . . C3 C 0.2236(3) 0.4401(4) 0.2070(3) 0.0354(9) Uani 1 1 d . . . H3A H 0.2769 0.4829 0.1863 0.043 Uiso 1 1 calc R . . H3B H 0.2224 0.3441 0.1872 0.043 Uiso 1 1 calc R . . C4 C 0.2294(3) 0.4361(5) 0.2982(2) 0.0418(11) Uani 1 1 d . . . H4A H 0.1774 0.3900 0.3192 0.050 Uiso 1 1 calc R . . H4B H 0.2795 0.3789 0.3134 0.050 Uiso 1 1 calc R . . C5 C 0.2378(3) 0.5733(5) 0.3384(2) 0.0405(11) Uani 1 1 d . . . H5A H 0.2452 0.5582 0.3967 0.049 Uiso 1 1 calc R . . H5B H 0.2905 0.6187 0.3183 0.049 Uiso 1 1 calc R . . C6 C 0.1891(3) 0.8027(5) 0.3646(3) 0.0474(13) Uani 1 1 d . . . H6A H 0.1890 0.7924 0.4236 0.057 Uiso 1 1 calc R . . H6B H 0.2478 0.8286 0.3476 0.057 Uiso 1 1 calc R . . C7 C 0.1275(4) 0.9129(5) 0.3409(3) 0.0470(12) Uani 1 1 d . . . H7A H 0.0694 0.8910 0.3613 0.056 Uiso 1 1 calc R . . H7B H 0.1457 1.0021 0.3640 0.056 Uiso 1 1 calc R . . C8 C 0.0472(3) 0.9897(5) 0.2221(3) 0.0419(12) Uani 1 1 d . . . H8A H 0.0519 0.9971 0.1630 0.050 Uiso 1 1 calc R . . H8B H 0.0461 1.0846 0.2437 0.050 Uiso 1 1 calc R . . C9 C -0.0382(3) 0.9226(5) 0.2415(3) 0.0477(12) Uani 1 1 d . . . H9A H -0.0846 0.9843 0.2225 0.057 Uiso 1 1 calc R . . H9B H -0.0434 0.9163 0.3006 0.057 Uiso 1 1 calc R . . C10 C -0.0540(2) 0.7797(5) 0.2065(4) 0.0442(9) Uani 1 1 d . . . H10A H -0.1128 0.7504 0.2212 0.053 Uiso 1 1 calc R . . H10B H -0.0515 0.7863 0.1473 0.053 Uiso 1 1 calc R . . C11 C -0.0006(3) 0.6492(5) 0.3214(2) 0.0391(11) Uani 1 1 d . . . H11A H -0.0424 0.5742 0.3309 0.047 Uiso 1 1 calc R . . H11B H -0.0235 0.7334 0.3470 0.047 Uiso 1 1 calc R . . C12 C 0.0845(3) 0.6112(5) 0.3622(2) 0.0383(11) Uani 1 1 d . . . H12A H 0.0816 0.6422 0.4187 0.046 Uiso 1 1 calc R . . H12B H 0.0893 0.5096 0.3628 0.046 Uiso 1 1 calc R . . C13 C 0.1585(3) 0.5112(4) 0.0804(2) 0.0300(9) Uani 1 1 d . . . H13A H 0.1064 0.5529 0.0566 0.036 Uiso 1 1 calc R . . H13B H 0.2079 0.5698 0.0653 0.036 Uiso 1 1 calc R . . C14 C 0.1711(3) 0.3715(4) 0.0439(2) 0.0305(9) Uani 1 1 d . . . C15 C 0.1020(3) 0.2903(5) 0.0208(2) 0.0348(10) Uani 1 1 d . . . H15 H 0.0454 0.3251 0.0272 0.042 Uiso 1 1 calc R . . C16 C 0.1131(3) 0.1598(5) -0.0114(2) 0.0405(11) Uani 1 1 d . . . H16 H 0.0648 0.1051 -0.0252 0.049 Uiso 1 1 calc R . . C17 C 0.1950(4) 0.1106(5) -0.0232(3) 0.0452(12) Uani 1 1 d . . . H17 H 0.2033 0.0209 -0.0445 0.054 Uiso 1 1 calc R . . C18 C 0.2649(3) 0.1908(5) -0.0043(3) 0.0426(12) Uani 1 1 d . . . H18 H 0.3213 0.1574 -0.0144 0.051 Uiso 1 1 calc R . . C19 C 0.2539(3) 0.3184(5) 0.0289(2) 0.0386(11) Uani 1 1 d . . . H19 H 0.3029 0.3722 0.0421 0.046 Uiso 1 1 calc R . . C20 C 0.2004(3) 1.0080(5) 0.2259(3) 0.0463(13) Uani 1 1 d . . . H20A H 0.2541 0.9656 0.2442 0.069 Uiso 1 1 calc R . . H20B H 0.1952 1.1003 0.2491 0.069 Uiso 1 1 calc R . . H20C H 0.2009 1.0148 0.1673 0.069 Uiso 1 1 calc R . . Cl1 Cl 0.02264(7) 0.75346(14) -0.08268(7) 0.0401(3) Uani 1 1 d . . . Cl2 Cl 0.35754(8) 0.76437(12) 0.10639(6) 0.0390(3) Uani 1 1 d . . . Cu1 Cu 0.13948(3) 0.72084(5) 0.20997(2) 0.02943(11) Uani 1 1 d . . . N1 N 0.0061(2) 0.6735(4) 0.23250(18) 0.0340(8) Uani 1 1 d . . . N2 N 0.1493(2) 0.5143(4) 0.17178(17) 0.0306(8) Uani 1 1 d . . . N3 N 0.1643(2) 0.6680(4) 0.32609(19) 0.0369(9) Uani 1 1 d . . . N4 N 0.1261(3) 0.9218(4) 0.2520(2) 0.0373(9) Uani 1 1 d . . . O1 O 0.1379(2) 0.8070(3) 0.09940(15) 0.0402(7) Uani 1 1 d . . . H21A H 0.0864 0.7881 0.0778 0.060 Uiso 1 1 d . . . H21B H 0.1850 0.7694 0.0754 0.060 Uiso 1 1 d . . . O2 O 0.0643(3) 0.6266(4) -0.0891(3) 0.0820(13) Uani 1 1 d . . . O3 O -0.0533(2) 0.7534(4) -0.12880(18) 0.0592(10) Uani 1 1 d . . . O4 O 0.0016(3) 0.7821(7) -0.0018(2) 0.104(2) Uani 1 1 d . . . O5 O 0.0795(3) 0.8570(5) -0.1115(3) 0.0905(15) Uani 1 1 d . . . O6 O 0.3127(2) 0.7367(4) 0.18086(16) 0.0563(9) Uani 1 1 d . . . O7 O 0.4362(2) 0.8241(5) 0.1221(3) 0.0780(13) Uani 1 1 d . . . O8 O 0.3057(3) 0.8550(4) 0.0612(2) 0.0615(11) Uani 1 1 d . . . O9 O 0.3703(2) 0.6391(3) 0.06561(17) 0.0470(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.034(2) 0.037(3) 0.032(2) -0.0014(16) -0.0025(17) -0.002(2) C2 0.037(2) 0.031(2) 0.025(2) -0.0040(16) 0.0043(16) -0.0044(19) C3 0.037(2) 0.036(2) 0.0333(19) 0.005(3) 0.007(2) 0.0051(18) C4 0.036(3) 0.057(3) 0.032(2) 0.007(2) 0.0002(18) 0.011(2) C5 0.042(3) 0.055(3) 0.025(2) 0.0027(19) -0.0064(18) 0.004(2) C6 0.055(3) 0.054(4) 0.033(2) -0.010(2) -0.006(2) -0.011(3) C7 0.056(3) 0.047(3) 0.038(2) -0.018(2) 0.005(2) -0.007(3) C8 0.050(3) 0.031(2) 0.045(3) -0.004(2) 0.008(2) 0.005(2) C9 0.043(3) 0.050(3) 0.050(3) 0.002(2) 0.011(2) 0.007(3) C10 0.036(2) 0.050(2) 0.046(2) 0.006(3) 0.003(3) -0.002(2) C11 0.043(3) 0.045(3) 0.029(2) -0.0044(19) 0.0088(18) -0.004(2) C12 0.047(3) 0.048(3) 0.0203(18) -0.0018(18) 0.0065(18) -0.009(2) C13 0.035(3) 0.032(2) 0.0231(17) 0.0005(15) 0.0045(15) -0.0023(19) C14 0.036(2) 0.030(2) 0.0259(18) 0.0038(16) 0.0056(16) -0.0005(19) C15 0.036(2) 0.039(3) 0.0290(18) -0.0029(19) -0.0031(16) 0.000(2) C16 0.055(3) 0.036(3) 0.031(2) -0.0029(19) -0.003(2) -0.002(2) C17 0.061(3) 0.042(3) 0.032(2) -0.0077(19) 0.005(2) 0.007(3) C18 0.047(3) 0.040(3) 0.041(2) -0.007(2) 0.008(2) 0.006(2) C19 0.043(3) 0.040(3) 0.032(2) -0.0036(18) 0.0073(19) -0.005(2) C20 0.053(3) 0.041(3) 0.045(3) -0.009(2) 0.004(2) -0.009(2) Cl1 0.0438(5) 0.0406(6) 0.0360(5) -0.0033(4) -0.0091(5) 0.0025(6) Cl2 0.0367(6) 0.0411(6) 0.0392(5) -0.0015(5) 0.0006(5) 0.0028(6) Cu1 0.0324(2) 0.0322(2) 0.02373(18) -0.0020(3) -0.0012(3) -0.0011(3) N1 0.0308(19) 0.040(2) 0.0310(17) 0.0000(13) 0.0007(14) 0.0010(17) N2 0.0356(19) 0.0318(19) 0.0246(14) 0.0001(13) -0.0011(15) -0.0025(18) N3 0.043(2) 0.044(2) 0.0237(15) -0.0053(15) -0.0048(14) 0.0016(17) N4 0.044(2) 0.029(2) 0.0385(19) -0.0106(16) 0.0136(17) -0.0038(18) O1 0.0447(17) 0.045(2) 0.0305(13) -0.0023(12) -0.0040(14) 0.0042(17) O2 0.090(3) 0.059(3) 0.096(3) -0.010(2) -0.025(3) 0.027(2) O3 0.059(2) 0.073(3) 0.0455(17) -0.0053(19) -0.0220(15) 0.004(2) O4 0.058(3) 0.214(6) 0.0409(18) -0.030(3) -0.0090(18) 0.037(3) O5 0.091(3) 0.076(4) 0.104(4) 0.018(3) -0.017(3) -0.039(3) O6 0.061(2) 0.074(3) 0.0336(14) 0.0051(16) 0.0109(14) 0.006(2) O7 0.042(2) 0.093(3) 0.099(3) -0.028(3) 0.005(2) -0.015(2) O8 0.070(3) 0.063(3) 0.051(2) 0.0256(18) 0.0155(19) 0.025(2) O9 0.060(2) 0.043(2) 0.0375(15) -0.0077(14) 0.0125(16) 0.0013(19) _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 1.477(5) . ? C1 C2 1.500(6) . ? C2 N2 1.491(5) . ? C3 N2 1.485(5) . ? C3 C4 1.524(6) . ? C4 C5 1.498(7) . ? C5 N3 1.482(6) . ? C6 C7 1.491(7) . ? C6 N3 1.508(6) . ? C7 N4 1.485(6) . ? C8 N4 1.481(6) . ? C8 C9 1.517(6) . ? C9 C10 1.526(7) . ? C10 N1 1.459(6) . ? C11 N1 1.505(5) . ? C11 C12 1.534(6) . ? C12 N3 1.488(5) . ? C13 C14 1.501(6) . ? C13 N2 1.530(4) . ? C14 C15 1.389(6) . ? C14 C19 1.410(6) . ? C15 C16 1.388(6) . ? C16 C17 1.376(7) . ? C17 C18 1.376(7) . ? C18 C19 1.370(7) . ? C20 N4 1.494(6) . ? Cl1 O2 1.397(4) . ? Cl1 O3 1.410(3) . ? Cl1 O4 1.415(4) . ? Cl1 O5 1.424(5) . ? Cl2 O7 1.381(4) . ? Cl2 O9 1.409(3) . ? Cl2 O8 1.412(4) . ? Cl2 O6 1.450(3) . ? Cu1 O1 2.025(3) . ? Cu1 N3 2.041(3) . ? Cu1 N4 2.085(4) . ? Cu1 N2 2.111(3) . ? Cu1 N1 2.159(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 112.3(3) . . ? N2 C2 C1 111.4(3) . . ? N2 C3 C4 116.9(4) . . ? C5 C4 C3 115.4(4) . . ? N3 C5 C4 115.0(4) . . ? C7 C6 N3 110.2(4) . . ? N4 C7 C6 108.4(4) . . ? N4 C8 C9 117.6(4) . . ? C8 C9 C10 116.8(4) . . ? N1 C10 C9 115.3(4) . . ? N1 C11 C12 114.5(3) . . ? N3 C12 C11 116.9(3) . . ? C14 C13 N2 115.8(3) . . ? C15 C14 C19 116.8(4) . . ? C15 C14 C13 121.6(4) . . ? C19 C14 C13 121.5(4) . . ? C16 C15 C14 122.0(4) . . ? C17 C16 C15 119.3(4) . . ? C16 C17 C18 120.3(4) . . ? C19 C18 C17 120.4(5) . . ? C18 C19 C14 121.2(4) . . ? O2 Cl1 O3 110.3(3) . . ? O2 Cl1 O4 110.7(3) . . ? O3 Cl1 O4 109.0(2) . . ? O2 Cl1 O5 108.0(3) . . ? O3 Cl1 O5 109.7(3) . . ? O4 Cl1 O5 109.0(3) . . ? O7 Cl2 O9 109.2(2) . . ? O7 Cl2 O8 110.3(3) . . ? O9 Cl2 O8 111.2(2) . . ? O7 Cl2 O6 110.1(2) . . ? O9 Cl2 O6 108.7(2) . . ? O8 Cl2 O6 107.3(2) . . ? O1 Cu1 N3 166.04(14) . . ? O1 Cu1 N4 85.28(13) . . ? N3 Cu1 N4 86.30(15) . . ? O1 Cu1 N2 96.85(12) . . ? N3 Cu1 N2 91.91(14) . . ? N4 Cu1 N2 177.34(14) . . ? O1 Cu1 N1 103.57(13) . . ? N3 Cu1 N1 87.90(13) . . ? N4 Cu1 N1 92.56(15) . . ? N2 Cu1 N1 85.39(14) . . ? C10 N1 C1 110.8(3) . . ? C10 N1 C11 111.0(4) . . ? C1 N1 C11 111.2(3) . . ? C10 N1 Cu1 114.5(3) . . ? C1 N1 Cu1 103.2(2) . . ? C11 N1 Cu1 105.8(2) . . ? C3 N2 C2 110.8(3) . . ? C3 N2 C13 108.1(3) . . ? C2 N2 C13 109.4(3) . . ? C3 N2 Cu1 113.5(2) . . ? C2 N2 Cu1 105.9(2) . . ? C13 N2 Cu1 109.0(2) . . ? C5 N3 C12 111.1(4) . . ? C5 N3 C6 106.4(3) . . ? C12 N3 C6 111.3(3) . . ? C5 N3 Cu1 115.7(2) . . ? C12 N3 Cu1 108.6(2) . . ? C6 N3 Cu1 103.5(3) . . ? C8 N4 C7 112.0(4) . . ? C8 N4 C20 107.1(4) . . ? C7 N4 C20 108.2(4) . . ? C8 N4 Cu1 112.8(3) . . ? C7 N4 Cu1 106.3(3) . . ? C20 N4 Cu1 110.5(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 N2 -54.8(4) . . . . ? N2 C3 C4 C5 -61.7(5) . . . . ? C3 C4 C5 N3 62.3(5) . . . . ? N3 C6 C7 N4 -56.8(5) . . . . ? N4 C8 C9 C10 -63.5(6) . . . . ? C8 C9 C10 N1 61.3(6) . . . . ? N1 C11 C12 N3 29.9(6) . . . . ? N2 C13 C14 C15 89.0(5) . . . . ? N2 C13 C14 C19 -93.1(4) . . . . ? C19 C14 C15 C16 3.5(6) . . . . ? C13 C14 C15 C16 -178.6(4) . . . . ? C14 C15 C16 C17 -2.0(6) . . . . ? C15 C16 C17 C18 -0.9(6) . . . . ? C16 C17 C18 C19 2.2(7) . . . . ? C17 C18 C19 C14 -0.6(7) . . . . ? C15 C14 C19 C18 -2.2(6) . . . . ? C13 C14 C19 C18 179.9(4) . . . . ? C9 C10 N1 C1 -172.3(4) . . . . ? C9 C10 N1 C11 63.6(5) . . . . ? C9 C10 N1 Cu1 -56.1(5) . . . . ? C2 C1 N1 C10 164.3(3) . . . . ? C2 C1 N1 C11 -71.7(4) . . . . ? C2 C1 N1 Cu1 41.3(4) . . . . ? C12 C11 N1 C10 -146.3(4) . . . . ? C12 C11 N1 C1 89.8(4) . . . . ? C12 C11 N1 Cu1 -21.6(4) . . . . ? O1 Cu1 N1 C10 -41.0(3) . . . . ? N3 Cu1 N1 C10 131.0(3) . . . . ? N4 Cu1 N1 C10 44.8(3) . . . . ? N2 Cu1 N1 C10 -136.9(3) . . . . ? O1 Cu1 N1 C1 79.5(2) . . . . ? N3 Cu1 N1 C1 -108.5(3) . . . . ? N4 Cu1 N1 C1 165.3(2) . . . . ? N2 Cu1 N1 C1 -16.4(2) . . . . ? O1 Cu1 N1 C11 -163.6(3) . . . . ? N3 Cu1 N1 C11 8.4(3) . . . . ? N4 Cu1 N1 C11 -77.8(3) . . . . ? N2 Cu1 N1 C11 100.5(3) . . . . ? C4 C3 N2 C2 -62.7(5) . . . . ? C4 C3 N2 C13 177.4(4) . . . . ? C4 C3 N2 Cu1 56.3(4) . . . . ? C1 C2 N2 C3 159.1(3) . . . . ? C1 C2 N2 C13 -81.8(4) . . . . ? C1 C2 N2 Cu1 35.6(3) . . . . ? C14 C13 N2 C3 52.9(4) . . . . ? C14 C13 N2 C2 -67.9(4) . . . . ? C14 C13 N2 Cu1 176.7(3) . . . . ? O1 Cu1 N2 C3 125.1(3) . . . . ? N3 Cu1 N2 C3 -44.1(3) . . . . ? N1 Cu1 N2 C3 -131.8(3) . . . . ? O1 Cu1 N2 C2 -113.1(2) . . . . ? N3 Cu1 N2 C2 77.7(2) . . . . ? N1 Cu1 N2 C2 -10.0(2) . . . . ? O1 Cu1 N2 C13 4.5(3) . . . . ? N3 Cu1 N2 C13 -164.6(3) . . . . ? N1 Cu1 N2 C13 107.6(3) . . . . ? C4 C5 N3 C12 63.7(5) . . . . ? C4 C5 N3 C6 -175.0(4) . . . . ? C4 C5 N3 Cu1 -60.6(5) . . . . ? C11 C12 N3 C5 -149.1(4) . . . . ? C11 C12 N3 C6 92.5(4) . . . . ? C11 C12 N3 Cu1 -20.8(4) . . . . ? C7 C6 N3 C5 168.2(4) . . . . ? C7 C6 N3 C12 -70.6(5) . . . . ? C7 C6 N3 Cu1 45.9(4) . . . . ? O1 Cu1 N3 C5 -82.3(7) . . . . ? N4 Cu1 N3 C5 -135.3(3) . . . . ? N2 Cu1 N3 C5 46.6(3) . . . . ? N1 Cu1 N3 C5 131.9(3) . . . . ? O1 Cu1 N3 C12 152.0(5) . . . . ? N4 Cu1 N3 C12 99.0(3) . . . . ? N2 Cu1 N3 C12 -79.0(3) . . . . ? N1 Cu1 N3 C12 6.3(3) . . . . ? O1 Cu1 N3 C6 33.6(7) . . . . ? N4 Cu1 N3 C6 -19.4(3) . . . . ? N2 Cu1 N3 C6 162.6(3) . . . . ? N1 Cu1 N3 C6 -112.1(3) . . . . ? C9 C8 N4 C7 -61.0(5) . . . . ? C9 C8 N4 C20 -179.4(4) . . . . ? C9 C8 N4 Cu1 58.9(4) . . . . ? C6 C7 N4 C8 159.6(4) . . . . ? C6 C7 N4 C20 -82.6(5) . . . . ? C6 C7 N4 Cu1 36.1(4) . . . . ? O1 Cu1 N4 C8 59.3(3) . . . . ? N3 Cu1 N4 C8 -131.9(3) . . . . ? N1 Cu1 N4 C8 -44.2(3) . . . . ? O1 Cu1 N4 C7 -177.7(3) . . . . ? N3 Cu1 N4 C7 -8.8(3) . . . . ? N1 Cu1 N4 C7 78.9(3) . . . . ? O1 Cu1 N4 C20 -60.6(3) . . . . ? N3 Cu1 N4 C20 108.3(3) . . . . ? N1 Cu1 N4 C20 -164.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.728 _refine_diff_density_min -2.462 _refine_diff_density_rms 0.103