# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Jerome Thibonnet' _publ_contact_author_email JEROME.THIBONNET@UNIV-TOURS.FR _publ_section_title ; Supramolecular and core-shell materials from self-assembled fibers ; _publ_requested_category FM loop_ _publ_author_name 'Jerome Thibonnet' 'A. Balland-Longeau' 'Alain Duchene' 'Louis Moreau' # END of CIF # Attachment 'TSC.revised3.cif' data_lmo247 _database_code_depnum_ccdc_archive 'CCDC 702134' #TrackingRef 'TSC.revised3.cif' _audit_creation_date 2009-11-12T14:28:09-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C22 H26 N2' _chemical_formula_sum 'C22 H26 N2' _chemical_formula_weight 318.45 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 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 12.5012(3) _cell_length_b 12.1365(3) _cell_length_c 12.7992(3) _cell_angle_alpha 90 _cell_angle_beta 102.692(1) _cell_angle_gamma 90 _cell_volume 1894.45(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 14667 _cell_measurement_theta_min 2.06 _cell_measurement_theta_max 28.21 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.06 _exptl_crystal_density_diffrn 1.117 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.065 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'Omega + Phi scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_reflns_av_R_equivalents 0.058 _diffrn_reflns_av_unetI/netI 0.0467 _diffrn_reflns_number 14667 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 28.21 _diffrn_reflns_theta_full 28.21 _diffrn_measured_fraction_theta_full 0.98 _diffrn_measured_fraction_theta_max 0.98 _reflns_number_total 4582 _reflns_number_gt 2961 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _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)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0989P)^2^+0.5677P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 4582 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1177 _refine_ls_R_factor_gt 0.0679 _refine_ls_wR_factor_ref 0.2223 _refine_ls_wR_factor_gt 0.1767 _refine_ls_goodness_of_fit_ref 1.103 _refine_ls_restrained_S_all 1.103 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.333 _refine_diff_density_min -0.303 _refine_diff_density_rms 0.096 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C5 C 0.7844(2) 0.46247(19) 0.44707(17) 0.0553(6) Uani 1 1 d . . . C6 C 0.70637(19) 0.4037(2) 0.37443(18) 0.0587(6) Uani 1 1 d . . . H6 H 0.6571 0.3588 0.3994 0.07 Uiso 1 1 calc R . . C8 C 0.7952(3) 0.4549(3) 0.5641(2) 0.0776(8) Uani 1 1 d . . . H8 H 0.8581 0.4869 0.6053 0.093 Uiso 1 1 calc R . . C9 C 0.7317(3) 0.4113(3) 0.6161(3) 0.1025(11) Uani 1 1 d . . . H9A H 0.6673 0.3778 0.5801 0.123 Uiso 1 1 calc R . . H9B H 0.7493 0.4128 0.6906 0.123 Uiso 1 1 calc R . . C1 C 0.77176(17) 0.4767(2) 0.10774(16) 0.0505(5) Uani 1 1 d . . . H1A H 0.829 0.5255 0.0951 0.061 Uiso 1 1 calc R . . H1B H 0.7887 0.403 0.087 0.061 Uiso 1 1 calc R . . C2 C 0.77243(16) 0.47705(17) 0.22532(15) 0.0449(5) Uani 1 1 d . . . C3 C 0.84824(19) 0.5368(2) 0.29790(17) 0.0560(6) Uani 1 1 d . . . H3 H 0.8962 0.5834 0.273 0.067 Uiso 1 1 calc R . . C4 C 0.8547(2) 0.5291(2) 0.40676(18) 0.0611(6) Uani 1 1 d . . . H4 H 0.9075 0.5697 0.4537 0.073 Uiso 1 1 calc R . . C7 C 0.70070(18) 0.41084(19) 0.26551(17) 0.0542(5) Uani 1 1 d . . . H7 H 0.6478 0.3705 0.2184 0.065 Uiso 1 1 calc R . . C10 C 0.34089(17) 0.52449(18) 0.07136(15) 0.0481(5) Uani 1 1 d . . . H10A H 0.3959 0.4798 0.1179 0.058 Uiso 1 1 calc R . . H10B H 0.2712 0.5102 0.0903 0.058 Uiso 1 1 calc R . . C11 C 0.36978(17) 0.64470(18) 0.09329(16) 0.0498(5) Uani 1 1 d . . . H11A H 0.3334 0.6882 0.0322 0.06 Uiso 1 1 calc R . . H11B H 0.3421 0.6685 0.1547 0.06 Uiso 1 1 calc R . . C12 C 0.5131(2) 0.77129(17) 0.17058(16) 0.0527(5) Uani 1 1 d . . . H12A H 0.4593 0.8256 0.1375 0.063 Uiso 1 1 calc R . . H12B H 0.5843 0.7963 0.1619 0.063 Uiso 1 1 calc R . . C13 C 0.51428(17) 0.76551(17) 0.28822(16) 0.0476(5) Uani 1 1 d . . . C14 C 0.5735(2) 0.6854(2) 0.35189(18) 0.0654(7) Uani 1 1 d . . . H14 H 0.6061 0.6293 0.3204 0.079 Uiso 1 1 calc R . . C15 C 0.5853(2) 0.6867(2) 0.46143(19) 0.0716(7) Uani 1 1 d . . . H15 H 0.6262 0.6319 0.5027 0.086 Uiso 1 1 calc R . . C16 C 0.5369(2) 0.7689(2) 0.51119(18) 0.0610(6) Uani 1 1 d . . . C17 C 0.4758(2) 0.8467(2) 0.4474(2) 0.0664(7) Uani 1 1 d . . . H17 H 0.4416 0.9017 0.4787 0.08 Uiso 1 1 calc R . . C18 C 0.46367(19) 0.84548(19) 0.33731(19) 0.0579(6) Uani 1 1 d . . . H18 H 0.421 0.8991 0.2959 0.069 Uiso 1 1 calc R . . C19 C 0.5526(3) 0.7748(3) 0.6289(2) 0.0870(9) Uani 1 1 d . . . H19 H 0.5245 0.8378 0.6544 0.104 Uiso 1 1 calc R . . C20 C 0.5980(4) 0.7081(4) 0.6999(3) 0.1247(15) Uani 1 1 d . . . H20A H 0.6281 0.6432 0.6807 0.15 Uiso 1 1 calc R . . H20B H 0.6015 0.7237 0.7717 0.15 Uiso 1 1 calc R . . C21 C 0.65314(17) 0.63116(17) 0.04423(16) 0.0473(5) Uani 1 1 d . . . H21A H 0.6902 0.6659 -0.0062 0.057 Uiso 1 1 calc R . . H21B H 0.6871 0.6574 0.1154 0.057 Uiso 1 1 calc R . . C22 C 0.53311(17) 0.66426(17) 0.01772(15) 0.0453(5) Uani 1 1 d . . . H22A H 0.5258 0.7367 -0.0151 0.054 Uiso 1 1 calc R . . H22B H 0.4919 0.6125 -0.0335 0.054 Uiso 1 1 calc R . . N1 N 0.66697(12) 0.51133(14) 0.04005(12) 0.0417(4) Uani 1 1 d . . . N2 N 0.48761(14) 0.66620(13) 0.11403(12) 0.0436(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C5 0.0649(14) 0.0558(13) 0.0424(11) 0.0010(10) 0.0060(10) 0.0091(11) C6 0.0610(13) 0.0625(14) 0.0533(13) 0.0106(11) 0.0142(10) -0.0041(11) C8 0.098(2) 0.0859(19) 0.0468(13) 0.0038(13) 0.0108(13) -0.0009(16) C9 0.127(3) 0.122(3) 0.0616(18) 0.0172(18) 0.0288(19) -0.006(2) C1 0.0444(11) 0.0644(13) 0.0420(10) -0.0035(10) 0.0081(8) 0.0031(10) C2 0.0420(10) 0.0511(11) 0.0392(10) -0.0009(8) 0.0037(8) 0.0054(9) C3 0.0566(13) 0.0612(13) 0.0487(12) -0.0026(10) 0.0082(10) -0.0095(11) C4 0.0702(15) 0.0645(15) 0.0431(11) -0.0083(10) 0.0002(10) -0.0087(12) C7 0.0507(12) 0.0617(14) 0.0463(11) 0.0000(10) 0.0025(9) -0.0059(10) C10 0.0525(11) 0.0600(13) 0.0332(9) -0.0047(9) 0.0126(8) -0.0059(10) C11 0.0532(12) 0.0550(12) 0.0414(10) -0.0086(9) 0.0108(9) 0.0064(10) C12 0.0718(14) 0.0424(11) 0.0432(11) -0.0047(9) 0.0113(10) -0.0001(10) C13 0.0524(11) 0.0454(11) 0.0434(11) -0.0100(9) 0.0071(9) -0.0019(9) C14 0.0848(17) 0.0663(15) 0.0454(12) -0.0060(11) 0.0148(11) 0.0242(13) C15 0.0844(18) 0.0816(18) 0.0453(12) 0.0010(12) 0.0065(12) 0.0201(15) C16 0.0587(13) 0.0800(17) 0.0466(12) -0.0178(12) 0.0164(10) -0.0129(12) C17 0.0693(15) 0.0719(16) 0.0644(15) -0.0229(13) 0.0283(13) 0.0029(13) C18 0.0608(13) 0.0547(13) 0.0588(13) -0.0111(11) 0.0147(11) 0.0067(11) C19 0.100(2) 0.113(3) 0.0517(15) -0.0173(16) 0.0251(15) -0.0136(19) C20 0.179(4) 0.141(3) 0.0516(18) 0.005(2) 0.019(2) -0.018(3) C21 0.0515(11) 0.0480(11) 0.0421(10) -0.0033(9) 0.0094(9) -0.0092(9) C22 0.0561(12) 0.0459(11) 0.0331(9) 0.0013(8) 0.0084(8) 0.0005(9) N1 0.0424(9) 0.0484(9) 0.0328(8) -0.0029(7) 0.0053(6) -0.0008(7) N2 0.0531(9) 0.0432(9) 0.0341(8) -0.0060(7) 0.0087(7) -0.0015(7) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C5 C4 1.375(3) . ? C5 C6 1.388(3) . ? C5 C8 1.476(3) . ? C6 C7 1.383(3) . ? C8 C9 1.259(4) . ? C1 N1 1.464(2) . ? C1 C2 1.503(3) . ? C2 C3 1.379(3) . ? C2 C7 1.385(3) . ? C3 C4 1.381(3) . ? C10 N1 1.473(2) 3_665 ? C10 C11 1.514(3) . ? C11 N2 1.462(3) . ? C12 N2 1.466(2) . ? C12 C13 1.504(3) . ? C13 C14 1.376(3) . ? C13 C18 1.383(3) . ? C14 C15 1.377(3) . ? C15 C16 1.391(4) . ? C16 C17 1.367(4) . ? C16 C19 1.477(3) . ? C17 C18 1.383(3) . ? C19 C20 1.255(5) . ? C21 N1 1.467(3) . ? C21 C22 1.518(3) . ? C22 N2 1.467(2) . ? N1 C10 1.473(2) 3_665 ? 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 C4 C5 C6 117.6(2) . . ? C4 C5 C8 119.5(2) . . ? C6 C5 C8 122.8(2) . . ? C7 C6 C5 121.1(2) . . ? C9 C8 C5 129.4(3) . . ? N1 C1 C2 113.52(16) . . ? C3 C2 C7 117.42(19) . . ? C3 C2 C1 121.9(2) . . ? C7 C2 C1 120.58(19) . . ? C2 C3 C4 121.5(2) . . ? C5 C4 C3 121.2(2) . . ? C6 C7 C2 121.1(2) . . ? N1 C10 C11 115.22(17) 3_665 . ? N2 C11 C10 113.29(17) . . ? N2 C12 C13 114.00(17) . . ? C14 C13 C18 117.9(2) . . ? C14 C13 C12 120.77(19) . . ? C18 C13 C12 121.2(2) . . ? C13 C14 C15 121.2(2) . . ? C14 C15 C16 121.0(2) . . ? C17 C16 C15 117.6(2) . . ? C17 C16 C19 120.5(2) . . ? C15 C16 C19 121.9(3) . . ? C16 C17 C18 121.6(2) . . ? C17 C18 C13 120.7(2) . . ? C20 C19 C16 130.1(4) . . ? N1 C21 C22 111.89(16) . . ? N2 C22 C21 111.30(16) . . ? C1 N1 C21 111.11(16) . . ? C1 N1 C10 110.42(15) . 3_665 ? C21 N1 C10 110.15(15) . 3_665 ? C11 N2 C12 110.24(17) . . ? C11 N2 C22 113.95(15) . . ? C12 N2 C22 110.27(16) . . ? # END of CIF # Attachment 'TSC.Cu.revised3.cif' data_lmocu _database_code_depnum_ccdc_archive 'CCDC 744758' #TrackingRef 'TSC.Cu.revised3.cif' _audit_update_record ; 2009-12-08 # Formatted by publCIF ; _audit_creation_date 2009-11-12T14:36:48-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C44 H56 Cl2 Cu1 N4 O2' _chemical_formula_sum 'C44 H56 Cl2 Cu N4 O2' _chemical_formula_weight 807.37 _chemical_compound_source 'synthesis as described' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c n' _symmetry_space_group_name_Hall '-P 2n 2ab' _symmetry_Int_Tables_number 60 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y, z-1/2' _cell_length_a 24.2754(3) _cell_length_b 29.7421(5) _cell_length_c 11.8474(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 8553.8(2) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 49697 _cell_measurement_theta_min 1.08 _cell_measurement_theta_max 25.86 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.254 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3416 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.675 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.1123 _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'Omega + Phi scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_reflns_av_unetI/netI 0.0971 _diffrn_reflns_number 49697 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min -36 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.08 _diffrn_reflns_theta_max 25.86 _diffrn_reflns_theta_full 25.86 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _reflns_number_total 8272 _reflns_number_gt 3873 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _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)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1385P)^2^+14.1984P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8255 _refine_ls_number_parameters 483 _refine_ls_number_restraints 58 _refine_ls_R_factor_all 0.2114 _refine_ls_R_factor_gt 0.1018 _refine_ls_wR_factor_ref 0.3003 _refine_ls_wR_factor_gt 0.2317 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.051 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.639 _refine_diff_density_min -0.499 _refine_diff_density_rms 0.084 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 0.2906(3) 0.1801(2) 0.3680(6) 0.0668(18) Uani 1 1 d . . . H1A H 0.2729 0.2059 0.3339 0.080 Uiso 1 1 calc R . . H1B H 0.2691 0.1718 0.4339 0.080 Uiso 1 1 calc R . . C2 C 0.2886(3) 0.1415(2) 0.2849(6) 0.072(2) Uani 1 1 d D . . C3 C 0.3018(3) 0.1464(3) 0.1716(6) 0.082(2) Uani 1 1 d D . . H3 H 0.3112 0.1746 0.1441 0.098 Uiso 1 1 calc R . . C4 C 0.3013(3) 0.1099(3) 0.0987(7) 0.098(3) Uani 1 1 d D . . H4 H 0.3113 0.1139 0.0236 0.118 Uiso 1 1 calc R . . C5 C 0.2864(4) 0.0684(3) 0.1350(10) 0.112(3) Uani 1 1 d DU A . C6 C 0.2708(4) 0.0622(3) 0.2432(9) 0.122(4) Uani 1 1 d D . . H6 H 0.2594 0.0339 0.2672 0.146 Uiso 1 1 calc R . . C7 C 0.2719(4) 0.0987(3) 0.3206(8) 0.100(3) Uani 1 1 d D . . H7 H 0.2614 0.0941 0.3952 0.120 Uiso 1 1 calc R . . C8 C 0.2852(6) 0.0292(4) 0.0581(11) 0.183(6) Uani 1 1 d DU . . H8A H 0.2923 0.0357 -0.0172 0.220 Uiso 0.50 1 d PR A . H8B H 0.2683 0.0008 0.0870 0.220 Uiso 0.50 1 d PR . . C9 C 0.2807(13) -0.0072(5) 0.0646(19) 0.210(10) Uani 0.50 1 d PDU A 1 H9A H 0.2920 -0.0255 0.0054 0.252 Uiso 0.50 1 calc PR A 1 H9B H 0.2656 -0.0199 0.1294 0.252 Uiso 0.50 1 calc PR A 1 C91 C 0.3029(13) 0.0255(7) -0.0251(18) 0.210(10) Uani 0.50 1 d PDU A 2 H91A H 0.3073 -0.0029 -0.0563 0.252 Uiso 0.50 1 calc PR A 2 H91B H 0.3137 0.0508 -0.0655 0.252 Uiso 0.50 1 calc PR A 2 C10 C 0.3773(3) 0.1539(3) 0.4546(7) 0.089(3) Uani 1 1 d . . . H10A H 0.3509 0.1318 0.4818 0.107 Uiso 1 1 calc R . . H10B H 0.3990 0.1399 0.3957 0.107 Uiso 1 1 calc R . . C11 C 0.4138(3) 0.1673(3) 0.5483(7) 0.091(2) Uani 1 1 d . . . H11A H 0.4298 0.1408 0.5826 0.110 Uiso 1 1 calc R . . H11B H 0.4435 0.1858 0.5192 0.110 Uiso 1 1 calc R . . C12 C 0.3447(3) 0.1635(3) 0.7024(6) 0.075(2) Uani 1 1 d . . . H12A H 0.3141 0.1543 0.6550 0.090 Uiso 1 1 calc R . . H12B H 0.3297 0.1815 0.7636 0.090 Uiso 1 1 calc R . . C13 C 0.3710(3) 0.1219(3) 0.7521(7) 0.083(2) Uani 1 1 d . . . C14 C 0.3609(5) 0.0796(3) 0.7028(9) 0.116(3) Uani 1 1 d . . . H14 H 0.3379 0.0780 0.6402 0.140 Uiso 1 1 calc R . . C15 C 0.3835(5) 0.0413(4) 0.7430(10) 0.143(4) Uani 1 1 d D . . H15 H 0.3751 0.0140 0.7087 0.172 Uiso 1 1 calc R . . C16 C 0.4179(6) 0.0421(4) 0.8322(15) 0.176(6) Uani 1 1 d DU . . C17 C 0.4281(5) 0.0839(4) 0.8860(11) 0.154(5) Uani 1 1 d D . . H17 H 0.4511 0.0850 0.9486 0.184 Uiso 1 1 calc R . . C18 C 0.4038(4) 0.1236(3) 0.8457(8) 0.112(3) Uani 1 1 d . . . H18 H 0.4099 0.1508 0.8825 0.134 Uiso 1 1 calc R . . C19 C 0.4426(8) 0.0007(4) 0.8808(16) 0.261(9) Uani 1 1 d DU . . H19 H 0.4648 0.0054 0.9437 0.314 Uiso 1 1 calc R . . C20 C 0.4384(7) -0.0378(4) 0.8519(17) 0.297(12) Uani 1 1 d DU . . H20A H 0.4169 -0.0452 0.7897 0.357 Uiso 1 1 calc R . . H20B H 0.4567 -0.0602 0.8917 0.357 Uiso 1 1 calc R . . C21 C 0.4216(3) 0.2205(3) 0.7114(7) 0.088(2) Uani 1 1 d . . . H21A H 0.4035 0.2258 0.7831 0.105 Uiso 1 1 calc R . . H21B H 0.4549 0.2034 0.7259 0.105 Uiso 1 1 calc R . . C22 C 0.4361(3) 0.2638(3) 0.6592(7) 0.086(2) Uani 1 1 d . . . H22A H 0.4581 0.2814 0.7111 0.103 Uiso 1 1 calc R . . H22B H 0.4576 0.2587 0.5914 0.103 Uiso 1 1 calc R . . C23 C 0.3558(3) 0.3061(3) 0.7317(6) 0.073(2) Uani 1 1 d . . . H23A H 0.3236 0.3223 0.7054 0.088 Uiso 1 1 calc R . . H23B H 0.3429 0.2810 0.7767 0.088 Uiso 1 1 calc R . . C24 C 0.3887(3) 0.3366(3) 0.8059(6) 0.077(2) Uani 1 1 d . . . C25 C 0.4144(3) 0.3209(3) 0.9024(6) 0.088(2) Uani 1 1 d . . . H25 H 0.4100 0.2910 0.9239 0.106 Uiso 1 1 calc R . . C26 C 0.4468(3) 0.3495(3) 0.9674(7) 0.098(3) Uani 1 1 d D . . H26 H 0.4633 0.3384 1.0326 0.118 Uiso 1 1 calc R . . C27 C 0.4552(4) 0.3939(4) 0.9382(9) 0.106(3) Uani 1 1 d DU . . C28 C 0.4278(4) 0.4097(4) 0.8444(9) 0.120(3) Uani 1 1 d D . . H28 H 0.4316 0.4397 0.8237 0.144 Uiso 1 1 calc R . . C29 C 0.3952(4) 0.3821(3) 0.7815(7) 0.101(3) Uani 1 1 d . . . H29 H 0.3766 0.3940 0.7198 0.121 Uiso 1 1 calc R . . C30 C 0.4910(4) 0.4242(4) 1.0056(11) 0.157(5) Uani 1 1 d DU . . H30 H 0.4989 0.4518 0.9724 0.188 Uiso 1 1 calc R . . C31 C 0.5118(5) 0.4181(5) 1.0989(12) 0.187(7) Uani 1 1 d DU . . H31A H 0.5057 0.3913 1.1371 0.224 Uiso 1 1 calc R . . H31B H 0.5336 0.4403 1.1313 0.224 Uiso 1 1 calc R . . C32 C 0.3986(3) 0.3265(3) 0.5492(6) 0.083(2) Uani 1 1 d . . . H32A H 0.3703 0.3494 0.5558 0.099 Uiso 1 1 calc R . . H32B H 0.4335 0.3401 0.5698 0.099 Uiso 1 1 calc R . . C33 C 0.4013(3) 0.3114(3) 0.4348(7) 0.085(2) Uani 1 1 d . . . H33A H 0.4331 0.2919 0.4254 0.102 Uiso 1 1 calc R . . H33B H 0.4058 0.3370 0.3851 0.102 Uiso 1 1 calc R . . C34 C 0.3026(3) 0.3181(2) 0.3906(6) 0.0700(19) Uani 1 1 d . . . H34A H 0.2727 0.3014 0.3557 0.084 Uiso 1 1 calc R . . H34B H 0.2903 0.3269 0.4654 0.084 Uiso 1 1 calc R . . C35 C 0.3123(3) 0.3600(3) 0.3227(7) 0.075(2) Uani 1 1 d D . . C36 C 0.3169(3) 0.4026(3) 0.3726(8) 0.099(3) Uani 1 1 d D . . H36 H 0.3110 0.4061 0.4496 0.119 Uiso 1 1 calc R . . C37 C 0.3302(4) 0.4393(3) 0.3065(10) 0.123(4) Uani 1 1 d D . . H37 H 0.3341 0.4672 0.3412 0.148 Uiso 1 1 calc R . . C38 C 0.3377(4) 0.4367(4) 0.1952(11) 0.122(4) Uani 1 1 d DU . . C39 C 0.3320(4) 0.3955(3) 0.1456(9) 0.111(3) Uani 1 1 d D . . H39 H 0.3366 0.3928 0.0680 0.134 Uiso 1 1 calc R . . C40 C 0.3199(4) 0.3586(3) 0.2074(7) 0.091(2) Uani 1 1 d D . . H40 H 0.3165 0.3312 0.1706 0.109 Uiso 1 1 calc R . . C41 C 0.3529(5) 0.4741(4) 0.1187(12) 0.199(8) Uani 1 1 d DU . . H41 H 0.3496 0.4682 0.0419 0.239 Uiso 1 1 calc R . . C42 C 0.3694(7) 0.5119(5) 0.1434(16) 0.311(15) Uani 1 1 d DU . . H42A H 0.3736 0.5200 0.2187 0.373 Uiso 1 1 calc R . . H42B H 0.3776 0.5325 0.0867 0.373 Uiso 1 1 calc R . . C43 C 0.3603(3) 0.2609(3) 0.2961(6) 0.078(2) Uani 1 1 d . . . H43A H 0.3259 0.2589 0.2546 0.093 Uiso 1 1 calc R . . H43B H 0.3869 0.2766 0.2493 0.093 Uiso 1 1 calc R . . C44 C 0.3807(3) 0.2153(3) 0.3218(6) 0.081(2) Uani 1 1 d . . . H44A H 0.3807 0.1974 0.2534 0.098 Uiso 1 1 calc R . . H44B H 0.4183 0.2171 0.3492 0.098 Uiso 1 1 calc R . . N1 N 0.3466(2) 0.1937(2) 0.4061(5) 0.0668(15) Uani 1 1 d . . . N2 N 0.3829(2) 0.1927(2) 0.6336(5) 0.0760(17) Uani 1 1 d . . . N3 N 0.3858(2) 0.2879(2) 0.6312(5) 0.0753(17) Uani 1 1 d . . . N4 N 0.3513(2) 0.2868(2) 0.4037(5) 0.0672(15) Uani 1 1 d . . . O1 O 0.6590(3) 0.2202(3) 0.5508(5) 0.123(2) Uani 1 1 d . . . H1W H 0.6266 0.2211 0.5216 0.148 Uiso 1 1 d R . . H2W H 0.6846 0.2301 0.5096 0.148 Uiso 1 1 d R . . O2 O 0.5000 0.2909(5) 0.2500 0.080(4) Uani 0.50 2 d SP . . H3W H 0.5100 0.2710 0.3020 0.097 Uiso 0.50 1 d PR . . O3 O 0.5000 0.1445(5) 0.2500 0.121(6) Uani 0.50 2 d SP . . H4W H 0.5090 0.1644 0.2980 0.145 Uiso 0.50 1 d PR . . Cl1 Cl 0.25444(7) 0.24256(6) 0.60281(15) 0.0736(6) Uani 1 1 d . . . Cl2 Cl 0.53870(10) 0.22310(11) 0.4420(2) 0.1224(10) Uani 1 1 d . . . Cu1 Cu 0.34490(3) 0.24075(3) 0.53362(6) 0.0592(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.060(4) 0.075(5) 0.066(4) 0.001(4) 0.001(3) -0.006(4) C2 0.068(5) 0.070(5) 0.077(5) -0.004(4) -0.015(4) -0.004(4) C3 0.099(6) 0.079(5) 0.067(5) 0.001(4) -0.005(4) -0.015(4) C4 0.108(7) 0.114(8) 0.072(5) -0.037(5) -0.011(5) 0.004(6) C5 0.126(8) 0.084(7) 0.125(8) -0.020(6) -0.047(7) 0.015(6) C6 0.161(10) 0.069(6) 0.136(9) 0.004(6) -0.054(8) -0.025(6) C7 0.115(7) 0.095(7) 0.090(6) 0.003(5) -0.010(5) -0.029(5) C8 0.165(13) 0.142(9) 0.243(15) -0.092(10) -0.068(11) 0.047(10) C9 0.20(3) 0.147(11) 0.28(2) -0.129(16) -0.02(2) 0.029(19) C91 0.20(3) 0.147(11) 0.28(2) -0.129(16) -0.02(2) 0.029(19) C10 0.070(5) 0.087(6) 0.110(6) -0.040(5) -0.015(5) 0.022(4) C11 0.073(5) 0.108(6) 0.094(6) 0.009(5) 0.009(5) 0.019(5) C12 0.068(5) 0.089(5) 0.069(4) 0.009(4) -0.003(4) 0.002(4) C13 0.083(5) 0.085(6) 0.083(5) 0.020(5) -0.002(5) -0.001(5) C14 0.137(9) 0.093(7) 0.118(8) 0.021(6) -0.021(6) 0.003(6) C15 0.170(12) 0.097(8) 0.163(11) 0.020(8) -0.030(9) 0.001(8) C16 0.135(10) 0.116(10) 0.277(18) 0.038(12) -0.057(11) 0.026(8) C17 0.143(10) 0.150(11) 0.169(11) 0.053(10) -0.058(9) 0.015(9) C18 0.119(8) 0.109(7) 0.106(7) 0.017(6) -0.040(6) 0.012(6) C19 0.244(17) 0.119(10) 0.42(2) 0.073(15) -0.113(17) 0.040(13) C20 0.201(17) 0.136(13) 0.55(3) 0.12(2) -0.05(2) 0.040(13) C21 0.052(4) 0.119(7) 0.092(6) 0.009(5) -0.026(4) -0.005(4) C22 0.061(5) 0.102(6) 0.095(6) -0.027(5) -0.005(4) 0.003(4) C23 0.058(4) 0.090(5) 0.072(5) -0.005(4) -0.001(4) 0.007(4) C24 0.076(5) 0.087(6) 0.066(5) -0.023(4) -0.006(4) 0.003(4) C25 0.095(6) 0.100(6) 0.069(5) -0.013(5) -0.011(5) 0.006(5) C26 0.080(6) 0.130(8) 0.085(6) -0.018(6) -0.016(5) 0.023(6) C27 0.083(6) 0.114(8) 0.121(8) -0.040(6) -0.007(5) 0.005(6) C28 0.134(9) 0.102(7) 0.125(8) -0.023(7) -0.016(7) 0.011(7) C29 0.121(7) 0.092(7) 0.089(6) -0.022(5) -0.022(5) -0.002(6) C30 0.112(9) 0.166(12) 0.192(12) -0.090(10) -0.036(8) 0.013(8) C31 0.141(11) 0.193(13) 0.226(14) -0.110(12) -0.068(10) 0.024(10) C32 0.071(5) 0.089(6) 0.088(6) -0.003(5) 0.020(4) -0.021(4) C33 0.068(5) 0.094(6) 0.093(6) 0.013(5) 0.008(4) -0.004(4) C34 0.062(4) 0.075(5) 0.073(4) 0.004(4) 0.004(3) -0.006(4) C35 0.062(5) 0.081(6) 0.081(5) 0.017(4) 0.004(4) -0.002(4) C36 0.116(7) 0.074(6) 0.107(7) -0.013(5) -0.002(6) 0.012(5) C37 0.140(9) 0.046(5) 0.183(11) 0.012(7) -0.035(9) -0.008(5) C38 0.099(7) 0.123(9) 0.143(10) 0.052(8) 0.005(7) 0.009(6) C39 0.126(8) 0.099(7) 0.109(7) 0.029(6) 0.019(6) 0.010(6) C40 0.106(6) 0.076(5) 0.090(6) 0.019(5) 0.003(5) 0.004(5) C41 0.131(11) 0.141(11) 0.33(2) 0.110(12) 0.011(11) 0.022(9) C42 0.210(18) 0.173(14) 0.55(4) 0.159(19) -0.11(2) -0.041(14) C43 0.074(5) 0.092(6) 0.067(5) 0.010(4) 0.020(4) 0.013(4) C44 0.080(5) 0.092(6) 0.073(5) -0.024(4) 0.016(4) -0.022(5) N1 0.055(3) 0.076(4) 0.069(4) -0.001(3) 0.005(3) -0.006(3) N2 0.057(3) 0.102(5) 0.069(4) 0.008(3) 0.010(3) 0.009(3) N3 0.053(3) 0.103(5) 0.069(4) -0.017(3) 0.008(3) -0.004(3) N4 0.044(3) 0.075(4) 0.082(4) -0.003(3) 0.009(3) -0.005(3) O1 0.099(5) 0.181(7) 0.090(4) 0.010(4) 0.021(3) 0.000(4) O2 0.047(7) 0.109(11) 0.085(9) 0.000 0.046(7) 0.000 O3 0.095(12) 0.062(9) 0.207(19) 0.000 0.039(12) 0.000 Cl1 0.0493(10) 0.0906(13) 0.0808(12) 0.0059(10) 0.0108(8) 0.0027(9) Cl2 0.0800(15) 0.189(3) 0.0986(17) -0.0306(17) 0.0158(13) -0.0258(16) Cu1 0.0459(5) 0.0732(6) 0.0586(6) -0.0011(4) 0.0007(3) -0.0007(4) _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 1.489(8) . ? C1 C2 1.512(9) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.387(9) . ? C2 C7 1.404(10) . ? C3 C4 1.388(10) . ? C3 H3 0.9300 . ? C4 C5 1.355(12) . ? C4 H4 0.9300 . ? C5 C6 1.349(13) . ? C5 C8 1.479(8) . ? C6 C7 1.421(11) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C91 1.082(10) . ? C8 C9 1.091(10) . ? C8 H8A 0.9300 . ? C8 H8B 0.9997 . ? C9 H8B 0.4677 . ? C9 H9A 0.9300 . ? C9 H9B 0.9300 . ? C91 H8A 0.4082 . ? C91 H91A 0.9300 . ? C91 H91B 0.9300 . ? C10 C11 1.476(10) . ? C10 N1 1.511(9) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 N2 1.467(9) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 N2 1.509(9) . ? C12 C13 1.512(10) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C18 1.365(11) . ? C13 C14 1.410(12) . ? C14 C15 1.350(12) . ? C14 H14 0.9300 . ? C15 C16 1.348(16) . ? C15 H15 0.9300 . ? C16 C17 1.419(16) . ? C16 C19 1.485(8) . ? C17 C18 1.404(13) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 C20 1.199(9) . ? C19 H19 0.9300 . ? C20 H20A 0.9300 . ? C20 H20B 0.9300 . ? C21 C22 1.471(10) . ? C21 N2 1.555(9) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 N3 1.456(9) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C24 1.495(9) . ? C23 N3 1.497(8) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 C25 1.384(10) . ? C24 C29 1.391(11) . ? C25 C26 1.393(11) . ? C25 H25 0.9300 . ? C26 C27 1.379(13) . ? C26 H26 0.9300 . ? C27 C28 1.378(12) . ? C27 C30 1.487(8) . ? C28 C29 1.364(12) . ? C28 H28 0.9300 . ? C29 H29 0.9300 . ? C30 C31 1.228(15) . ? C30 H30 0.9300 . ? C31 H31A 0.9300 . ? C31 H31B 0.9300 . ? C32 C33 1.430(10) . ? C32 N3 1.536(9) . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C33 N4 1.465(9) . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C34 C35 1.503(9) . ? C34 N4 1.513(8) . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? C35 C40 1.379(10) . ? C35 C36 1.402(10) . ? C36 C37 1.382(12) . ? C36 H36 0.9300 . ? C37 C38 1.333(14) . ? C37 H37 0.9300 . ? C38 C39 1.365(14) . ? C38 C41 1.482(8) . ? C39 C40 1.351(11) . ? C39 H39 0.9300 . ? C40 H40 0.9300 . ? C41 C42 1.229(5) . ? C41 H41 0.9300 . ? C42 H42A 0.9300 . ? C42 H42B 0.9300 . ? C43 C44 1.477(10) . ? C43 N4 1.504(9) . ? C43 H43A 0.9700 . ? C43 H43B 0.9700 . ? C44 N1 1.448(8) . ? C44 H44A 0.9700 . ? C44 H44B 0.9700 . ? N1 Cu1 2.060(6) . ? N2 Cu1 2.073(6) . ? N3 Cu1 2.071(6) . ? N4 Cu1 2.065(6) . ? O1 H1W 0.8588 . ? O1 H2W 0.8427 . ? O2 H3W 0.8875 . ? O3 H4W 0.8495 . ? Cl1 Cu1 2.3444(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 N1 C1 C2 115.6(5) . . ? N1 C1 H1A 108.4 . . ? C2 C1 H1A 108.4 . . ? N1 C1 H1B 108.4 . . ? C2 C1 H1B 108.4 . . ? H1A C1 H1B 107.4 . . ? C3 C2 C7 116.9(7) . . ? C3 C2 C1 123.0(7) . . ? C7 C2 C1 120.1(7) . . ? C2 C3 C4 121.3(8) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? C5 C4 C3 121.1(8) . . ? C5 C4 H4 119.4 . . ? C3 C4 H4 119.4 . . ? C6 C5 C4 120.1(8) . . ? C6 C5 C8 118.1(10) . . ? C4 C5 C8 121.8(11) . . ? C5 C6 C7 120.3(9) . . ? C5 C6 H6 119.9 . . ? C7 C6 H6 119.9 . . ? C2 C7 C6 120.3(8) . . ? C2 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C91 C8 C9 90.2(18) . . ? C91 C8 C5 129.3(16) . . ? C9 C8 C5 137.8(15) . . ? C91 C8 H8A 21.8 . . ? C9 C8 H8A 107.0 . . ? C5 C8 H8A 115.1 . . ? C91 C8 H8B 112.9 . . ? C9 C8 H8B 25.4 . . ? C5 C8 H8B 117.6 . . ? H8A C8 H8B 125.5 . . ? C8 C9 H8B 66.3 . . ? C8 C9 H9A 120.0 . . ? H8B C9 H9A 156.6 . . ? C8 C9 H9B 120.0 . . ? H8B C9 H9B 59.0 . . ? H9A C9 H9B 120.0 . . ? C8 C91 H8A 57.7 . . ? C8 C91 H91A 120.0 . . ? H8A C91 H91A 147.0 . . ? C8 C91 H91B 120.0 . . ? H8A C91 H91B 72.3 . . ? H91A C91 H91B 120.0 . . ? C11 C10 N1 111.6(6) . . ? C11 C10 H10A 109.3 . . ? N1 C10 H10A 109.3 . . ? C11 C10 H10B 109.3 . . ? N1 C10 H10B 109.3 . . ? H10A C10 H10B 108.0 . . ? N2 C11 C10 110.5(6) . . ? N2 C11 H11A 109.6 . . ? C10 C11 H11A 109.6 . . ? N2 C11 H11B 109.6 . . ? C10 C11 H11B 109.6 . . ? H11A C11 H11B 108.1 . . ? N2 C12 C13 114.8(6) . . ? N2 C12 H12A 108.6 . . ? C13 C12 H12A 108.6 . . ? N2 C12 H12B 108.6 . . ? C13 C12 H12B 108.6 . . ? H12A C12 H12B 107.5 . . ? C18 C13 C14 118.0(8) . . ? C18 C13 C12 122.2(8) . . ? C14 C13 C12 119.8(8) . . ? C15 C14 C13 122.5(10) . . ? C15 C14 H14 118.8 . . ? C13 C14 H14 118.8 . . ? C16 C15 C14 120.9(11) . . ? C16 C15 H15 119.5 . . ? C14 C15 H15 119.5 . . ? C15 C16 C17 118.4(10) . . ? C15 C16 C19 122.7(12) . . ? C17 C16 C19 118.8(12) . . ? C18 C17 C16 120.8(11) . . ? C18 C17 H17 119.6 . . ? C16 C17 H17 119.6 . . ? C13 C18 C17 119.4(10) . . ? C13 C18 H18 120.3 . . ? C17 C18 H18 120.3 . . ? C20 C19 C16 130.3(13) . . ? C20 C19 H19 114.9 . . ? C16 C19 H19 114.9 . . ? C19 C20 H20A 120.0 . . ? C19 C20 H20B 120.0 . . ? H20A C20 H20B 120.0 . . ? C22 C21 N2 111.1(6) . . ? C22 C21 H21A 109.4 . . ? N2 C21 H21A 109.4 . . ? C22 C21 H21B 109.4 . . ? N2 C21 H21B 109.4 . . ? H21A C21 H21B 108.0 . . ? N3 C22 C21 109.1(6) . . ? N3 C22 H22A 109.9 . . ? C21 C22 H22A 109.9 . . ? N3 C22 H22B 109.9 . . ? C21 C22 H22B 109.9 . . ? H22A C22 H22B 108.3 . . ? C24 C23 N3 115.4(6) . . ? C24 C23 H23A 108.4 . . ? N3 C23 H23A 108.4 . . ? C24 C23 H23B 108.4 . . ? N3 C23 H23B 108.4 . . ? H23A C23 H23B 107.5 . . ? C25 C24 C29 116.8(7) . . ? C25 C24 C23 121.3(8) . . ? C29 C24 C23 121.9(7) . . ? C24 C25 C26 120.2(8) . . ? C24 C25 H25 119.9 . . ? C26 C25 H25 119.9 . . ? C27 C26 C25 122.1(8) . . ? C27 C26 H26 119.0 . . ? C25 C26 H26 119.0 . . ? C28 C27 C26 117.3(8) . . ? C28 C27 C30 120.5(10) . . ? C26 C27 C30 122.2(10) . . ? C29 C28 C27 120.9(10) . . ? C29 C28 H28 119.5 . . ? C27 C28 H28 119.5 . . ? C28 C29 C24 122.6(9) . . ? C28 C29 H29 118.7 . . ? C24 C29 H29 118.7 . . ? C31 C30 C27 129.3(13) . . ? C31 C30 H30 115.3 . . ? C27 C30 H30 115.3 . . ? C30 C31 H31A 120.0 . . ? C30 C31 H31B 120.0 . . ? H31A C31 H31B 120.0 . . ? C33 C32 N3 111.9(6) . . ? C33 C32 H32A 109.2 . . ? N3 C32 H32A 109.2 . . ? C33 C32 H32B 109.2 . . ? N3 C32 H32B 109.2 . . ? H32A C32 H32B 107.9 . . ? C32 C33 N4 111.0(6) . . ? C32 C33 H33A 109.4 . . ? N4 C33 H33A 109.4 . . ? C32 C33 H33B 109.4 . . ? N4 C33 H33B 109.4 . . ? H33A C33 H33B 108.0 . . ? C35 C34 N4 116.3(5) . . ? C35 C34 H34A 108.2 . . ? N4 C34 H34A 108.2 . . ? C35 C34 H34B 108.2 . . ? N4 C34 H34B 108.2 . . ? H34A C34 H34B 107.4 . . ? C40 C35 C36 115.7(7) . . ? C40 C35 C34 121.8(7) . . ? C36 C35 C34 122.5(7) . . ? C37 C36 C35 119.6(9) . . ? C37 C36 H36 120.2 . . ? C35 C36 H36 120.2 . . ? C38 C37 C36 123.1(10) . . ? C38 C37 H37 118.5 . . ? C36 C37 H37 118.5 . . ? C37 C38 C39 117.6(9) . . ? C37 C38 C41 126.5(12) . . ? C39 C38 C41 115.9(11) . . ? C40 C39 C38 121.1(10) . . ? C40 C39 H39 119.4 . . ? C38 C39 H39 119.4 . . ? C39 C40 C35 122.9(9) . . ? C39 C40 H40 118.6 . . ? C35 C40 H40 118.6 . . ? C42 C41 C38 128.5(14) . . ? C42 C41 H41 115.7 . . ? C38 C41 H41 115.7 . . ? C41 C42 H42A 120.0 . . ? C41 C42 H42B 120.0 . . ? H42A C42 H42B 120.0 . . ? C44 C43 N4 110.1(6) . . ? C44 C43 H43A 109.6 . . ? N4 C43 H43A 109.6 . . ? C44 C43 H43B 109.6 . . ? N4 C43 H43B 109.6 . . ? H43A C43 H43B 108.2 . . ? N1 C44 C43 111.0(6) . . ? N1 C44 H44A 109.4 . . ? C43 C44 H44A 109.4 . . ? N1 C44 H44B 109.4 . . ? C43 C44 H44B 109.4 . . ? H44A C44 H44B 108.0 . . ? C44 N1 C1 115.7(5) . . ? C44 N1 C10 109.2(6) . . ? C1 N1 C10 110.6(5) . . ? C44 N1 Cu1 102.4(4) . . ? C1 N1 Cu1 112.9(4) . . ? C10 N1 Cu1 105.3(4) . . ? C11 N2 C12 113.1(6) . . ? C11 N2 C21 111.8(6) . . ? C12 N2 C21 110.9(5) . . ? C11 N2 Cu1 100.8(4) . . ? C12 N2 Cu1 115.6(4) . . ? C21 N2 Cu1 104.0(4) . . ? C22 N3 C23 113.9(6) . . ? C22 N3 C32 110.1(6) . . ? C23 N3 C32 109.4(6) . . ? C22 N3 Cu1 101.2(4) . . ? C23 N3 Cu1 117.1(4) . . ? C32 N3 Cu1 104.5(4) . . ? C33 N4 C43 110.3(6) . . ? C33 N4 C34 111.5(6) . . ? C43 N4 C34 110.0(5) . . ? C33 N4 Cu1 101.9(4) . . ? C43 N4 Cu1 107.7(4) . . ? C34 N4 Cu1 115.2(4) . . ? H1W O1 H2W 115.7 . . ? N1 Cu1 N4 84.4(2) . . ? N1 Cu1 N3 149.3(2) . . ? N4 Cu1 N3 86.1(2) . . ? N1 Cu1 N2 86.6(2) . . ? N4 Cu1 N2 148.2(2) . . ? N3 Cu1 N2 86.3(3) . . ? N1 Cu1 Cl1 106.91(15) . . ? N4 Cu1 Cl1 108.39(15) . . ? N3 Cu1 Cl1 103.77(16) . . ? N2 Cu1 Cl1 103.44(16) . . ?