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 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Horike, Satoshi' _publ_contact_author_email horike@sbchem.kyoto-u.ac.jp _publ_section_title ; Modification of Flexible Part in Cu2+ Interdigitated Framework for CH4/CO2 Separation ; # Attachment '- 1degas-2.cif' _audit_creation_date 2008-05-20 _audit_creation_method 'by CrystalStructure 3.8' _audit_update_record ? loop_ _publ_author_name Y.Inubushi S.Horike T.Fukushima G.Akiyama R.Matsuda S.Kitagawa # #============================================================================== data__sc0271x _database_code_depnum_ccdc_archive 'CCDC 776333' #TrackingRef '- 1degas-2.cif' _audit_creation_date 2008-05-20 _audit_creation_method 'by CrystalStructure 3.8' _audit_update_record ? #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C24 H18 Cu N2 O8 ' _chemical_formula_moiety 'C24 H18 Cu N2 O8 ' _chemical_formula_weight 525.96 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,-Y,-Z #------------------------------------------------------------------------------ _cell_length_a 6.6917(17) _cell_length_b 8.125(2) _cell_length_c 11.044(3) _cell_angle_alpha 84.075(17) _cell_angle_beta 75.581(14) _cell_angle_gamma 77.251(18) _cell_volume 566.5(3) _cell_formula_units_Z 1 _cell_measurement_reflns_used 1512 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 25.3 _cell_measurement_temperature 93.1 #------------------------------------------------------------------------------ _exptl_crystal_description platelet _exptl_crystal_colour green _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.02 _exptl_crystal_density_diffrn 1.542 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 269.00 _exptl_absorpt_coefficient_mu 1.018 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.899 _exptl_absorpt_correction_T_max 0.980 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 93(1) _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_measurement_device_type 'Rigaku Saturn' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.31 _diffrn_reflns_number 8289 _diffrn_reflns_av_R_equivalents 0.038 _diffrn_reflns_theta_max 25.34 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.34 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 2058 _reflns_number_gt 1812 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0393 _refine_ls_wR_factor_ref 0.0955 _refine_ls_hydrogen_treatment geom _refine_ls_number_reflns 2058 _refine_ls_number_parameters 167 _refine_ls_goodness_of_fit_ref 1.150 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0388P)^2^+0.5016P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max 0.0000 _refine_diff_density_max 0.53 _refine_diff_density_min -0.53 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; Cu Cu 0.320 1.265 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; N N 0.006 0.003 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.011 0.006 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 Cu(1) Cu 0.5000 0.5000 0.5000 0.01953(17) Uani 1.00 2 d S . . O(1) O 0.3240(3) 0.7288(2) 0.52415(16) 0.0190(4) Uani 1.00 1 d . . . O(2) O 0.0756(3) 0.6454(2) 0.68000(17) 0.0223(4) Uani 1.00 1 d . . . O(3) O -0.0688(3) 0.8265(2) 0.87316(19) 0.0270(5) Uani 1.00 1 d . . . O(4) O 0.1755(3) 1.3607(2) 0.56125(18) 0.0208(4) Uani 1.00 1 d . . . N(1) N 0.5335(3) 0.4889(2) 0.6746(2) 0.0172(5) Uani 1.00 1 d . . . C(1) C 0.5727(4) 0.6211(3) 0.7222(2) 0.0208(6) Uani 1.00 1 d . . . C(2) C 0.5610(4) 0.6294(3) 0.8477(2) 0.0194(6) Uani 1.00 1 d . . . C(3) C 0.5063(4) 0.4975(3) 0.9318(2) 0.0154(5) Uani 1.00 1 d . . . C(4) C 0.4672(4) 0.3601(3) 0.8814(2) 0.0190(6) Uani 1.00 1 d . . . C(5) C 0.4844(4) 0.3591(3) 0.7549(2) 0.0191(6) Uani 1.00 1 d . . . C(6) C 0.1731(4) 0.7568(3) 0.6206(2) 0.0178(5) Uani 1.00 1 d . . . C(7) C 0.1117(4) 0.9299(3) 0.6693(2) 0.0179(5) Uani 1.00 1 d . . . C(8) C -0.0017(4) 0.9546(3) 0.7940(2) 0.0194(6) Uani 1.00 1 d . . . C(9) C -0.0449(4) 1.1135(3) 0.8417(2) 0.0225(6) Uani 1.00 1 d . . . C(10) C 0.0139(4) 1.2494(3) 0.7646(2) 0.0208(6) Uani 1.00 1 d . . . C(11) C 0.1190(4) 1.2271(3) 0.6401(2) 0.0180(5) Uani 1.00 1 d . . . C(12) C 0.1726(4) 1.0681(3) 0.5931(2) 0.0179(5) Uani 1.00 1 d . . . H(1) H -0.038(5) 0.746(4) 0.834(3) 0.0324 Uiso 1.00 1 c . . . H(2) H 0.122(5) 1.448(4) 0.593(2) 0.0249 Uiso 1.00 1 c . . . H(3) H 0.6101 0.7127 0.6668 0.025 Uiso 1.00 1 c R . . H(4) H 0.5904 0.7253 0.8770 0.023 Uiso 1.00 1 c R . . H(5) H 0.4287 0.2671 0.9347 0.023 Uiso 1.00 1 c R . . H(6) H 0.4607 0.2630 0.7226 0.023 Uiso 1.00 1 c R . . H(7) H -0.1147 1.1293 0.9270 0.027 Uiso 1.00 1 c R . . H(8) H -0.0180 1.3583 0.7972 0.025 Uiso 1.00 1 c R . . H(9) H 0.2507 1.0523 0.5091 0.021 Uiso 1.00 1 c R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Cu(1) 0.0343(3) 0.0127(2) 0.0122(2) -0.0045(2) -0.0059(2) -0.00240(18) O(1) 0.0335(11) 0.0116(9) 0.0109(9) -0.0039(8) -0.0036(8) -0.0013(7) O(2) 0.0339(11) 0.0120(9) 0.0213(10) -0.0095(8) -0.0026(8) -0.0012(8) O(3) 0.0425(13) 0.0155(10) 0.0201(11) -0.0127(9) 0.0051(9) -0.0035(8) O(4) 0.0333(11) 0.0089(9) 0.0182(10) -0.0060(8) -0.0010(8) -0.0010(7) N(1) 0.0246(12) 0.0118(11) 0.0139(11) -0.0039(9) -0.0008(9) -0.0030(9) C(1) 0.0310(16) 0.0156(13) 0.0160(14) -0.0101(12) -0.0012(12) -0.0002(11) C(2) 0.0284(15) 0.0151(13) 0.0169(13) -0.0092(11) -0.0040(11) -0.0031(11) C(3) 0.0183(13) 0.0133(12) 0.0124(13) -0.0012(10) -0.0013(10) -0.0011(10) C(4) 0.0284(15) 0.0154(13) 0.0134(13) -0.0082(11) -0.0032(11) 0.0029(11) C(5) 0.0292(15) 0.0126(13) 0.0175(14) -0.0070(11) -0.0067(12) -0.0008(11) C(6) 0.0275(15) 0.0134(13) 0.0145(13) -0.0037(11) -0.0086(12) -0.0018(11) C(7) 0.0245(14) 0.0133(13) 0.0182(13) -0.0053(11) -0.0073(11) -0.0026(11) C(8) 0.0240(14) 0.0153(13) 0.0192(14) -0.0058(11) -0.0035(11) -0.0020(11) C(9) 0.0302(16) 0.0173(14) 0.0179(14) -0.0064(12) 0.0011(12) -0.0038(11) C(10) 0.0265(15) 0.0140(13) 0.0211(14) -0.0042(11) -0.0016(12) -0.0076(11) C(11) 0.0224(14) 0.0128(13) 0.0202(14) -0.0060(11) -0.0059(11) 0.0008(11) C(12) 0.0263(15) 0.0150(13) 0.0125(13) -0.0046(11) -0.0043(11) -0.0016(10) #============================================================================== _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalStructure _computing_structure_solution SIR97 _computing_structure_refinement SHELXL _computing_publication_material 'CrystalStructure 3.8' _computing_molecular_graphics ? #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 Cu(1) O(1) 1.9734(16) yes . . Cu(1) O(1) 1.9734(16) yes . 2_666 Cu(1) N(1) 1.987(2) yes . . Cu(1) N(1) 1.987(2) yes . 2_666 O(1) C(6) 1.272(2) yes . . O(2) C(6) 1.265(3) yes . . O(3) C(8) 1.368(3) yes . . O(4) C(11) 1.379(3) yes . . N(1) C(1) 1.344(4) yes . . N(1) C(5) 1.350(3) yes . . C(1) C(2) 1.376(4) yes . . C(2) C(3) 1.394(3) yes . . C(3) C(3) 1.492(3) yes . 2_667 C(3) C(4) 1.398(4) yes . . C(4) C(5) 1.373(3) yes . . C(6) C(7) 1.492(3) yes . . C(7) C(8) 1.409(3) yes . . C(7) C(12) 1.404(3) yes . . C(8) C(9) 1.389(3) yes . . C(9) C(10) 1.389(3) yes . . C(10) C(11) 1.390(3) yes . . C(11) C(12) 1.382(3) yes . . O(3) H(1) 0.79(3) no . . O(4) H(2) 0.79(3) no . . C(1) H(3) 0.950 no . . C(2) H(4) 0.950 no . . C(4) H(5) 0.950 no . . C(5) H(6) 0.950 no . . C(9) H(7) 0.950 no . . C(10) H(8) 0.950 no . . C(12) H(9) 0.950 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 O(1) Cu(1) O(1) 180.00(11) yes . . 2_666 O(1) Cu(1) N(1) 89.78(7) yes . . . O(1) Cu(1) N(1) 90.22(7) yes . . 2_666 O(1) Cu(1) N(1) 90.22(7) yes 2_666 . . O(1) Cu(1) N(1) 89.78(7) yes 2_666 . 2_666 N(1) Cu(1) N(1) 180.00(12) yes . . 2_666 Cu(1) O(1) C(6) 119.98(15) yes . . . Cu(1) N(1) C(1) 121.28(17) yes . . . Cu(1) N(1) C(5) 120.5(2) yes . . . C(1) N(1) C(5) 117.5(2) yes . . . N(1) C(1) C(2) 122.8(2) yes . . . C(1) C(2) C(3) 120.2(2) yes . . . C(2) C(3) C(3) 121.4(2) yes . . 2_667 C(2) C(3) C(4) 116.6(2) yes . . . C(3) C(3) C(4) 122.0(2) yes 2_667 . . C(3) C(4) C(5) 120.2(2) yes . . . N(1) C(5) C(4) 122.8(2) yes . . . O(1) C(6) O(2) 123.9(2) yes . . . O(1) C(6) C(7) 118.2(2) yes . . . O(2) C(6) C(7) 117.9(2) yes . . . C(6) C(7) C(8) 119.9(2) yes . . . C(6) C(7) C(12) 120.6(2) yes . . . C(8) C(7) C(12) 119.5(2) yes . . . O(3) C(8) C(7) 122.7(2) yes . . . O(3) C(8) C(9) 117.5(2) yes . . . C(7) C(8) C(9) 119.7(2) yes . . . C(8) C(9) C(10) 120.0(2) yes . . . C(9) C(10) C(11) 120.5(2) yes . . . O(4) C(11) C(10) 121.5(2) yes . . . O(4) C(11) C(12) 118.4(2) yes . . . C(10) C(11) C(12) 120.2(2) yes . . . C(7) C(12) C(11) 120.0(2) yes . . . C(8) O(3) H(1) 107(2) no . . . C(11) O(4) H(2) 110(2) no . . . N(1) C(1) H(3) 118.6 no . . . C(2) C(1) H(3) 118.6 no . . . C(1) C(2) H(4) 119.9 no . . . C(3) C(2) H(4) 119.9 no . . . C(3) C(4) H(5) 119.9 no . . . C(5) C(4) H(5) 119.9 no . . . N(1) C(5) H(6) 118.6 no . . . C(4) C(5) H(6) 118.6 no . . . C(8) C(9) H(7) 120.0 no . . . C(10) C(9) H(7) 120.0 no . . . C(9) C(10) H(8) 119.8 no . . . C(11) C(10) H(8) 119.8 no . . . C(7) C(12) H(9) 120.0 no . . . C(11) C(12) H(9) 120.0 no . . . 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 O(1) Cu(1) N(1) C(1) -43.5(2) ? . . . . O(1) Cu(1) N(1) C(5) 125.83(19) ? . . . . N(1) Cu(1) O(1) C(6) -48.7(2) ? . . . . O(1) Cu(1) N(1) C(1) -136.5(2) ? . . 2_666 2_666 O(1) Cu(1) N(1) C(5) 54.17(19) ? . . 2_666 2_666 N(1) Cu(1) O(1) C(6) 131.3(2) ? 2_666 . . . O(1) Cu(1) N(1) C(1) 136.5(2) ? 2_666 . . . O(1) Cu(1) N(1) C(5) -54.17(19) ? 2_666 . . . N(1) Cu(1) O(1) C(6) -131.3(2) ? . . 2_666 2_666 O(1) Cu(1) N(1) C(1) 43.5(2) ? 2_666 . 2_666 2_666 O(1) Cu(1) N(1) C(5) -125.83(19) ? 2_666 . 2_666 2_666 N(1) Cu(1) O(1) C(6) 48.7(2) ? 2_666 . 2_666 2_666 Cu(1) O(1) C(6) O(2) -26.8(4) ? . . . . Cu(1) O(1) C(6) C(7) 151.2(2) ? . . . . Cu(1) N(1) C(1) C(2) 168.5(2) ? . . . . Cu(1) N(1) C(5) C(4) -167.7(2) ? . . . . C(1) N(1) C(5) C(4) 2.0(3) ? . . . . C(5) N(1) C(1) C(2) -1.2(3) ? . . . . N(1) C(1) C(2) C(3) -0.1(3) ? . . . . C(1) C(2) C(3) C(4) 0.5(3) ? . . . . C(1) C(2) C(3) C(3) 179.6(2) ? . . . 2_667 C(2) C(3) C(3) C(4) 1.0(3) ? . . 2_667 2_667 C(2) C(3) C(4) C(5) 0.3(3) ? . . . . C(3) C(3) C(4) C(5) -178.8(2) ? 2_667 . . . C(4) C(3) C(3) C(2) -1.0(3) ? . . 2_667 2_667 C(3) C(4) C(5) N(1) -1.6(4) ? . . . . O(1) C(6) C(7) C(8) -159.4(2) ? . . . . O(1) C(6) C(7) C(12) 18.3(4) ? . . . . O(2) C(6) C(7) C(8) 18.7(4) ? . . . . O(2) C(6) C(7) C(12) -163.6(2) ? . . . . C(6) C(7) C(8) O(3) -3.2(4) ? . . . . C(6) C(7) C(8) C(9) 175.2(2) ? . . . . C(6) C(7) C(12) C(11) -178.5(2) ? . . . . C(8) C(7) C(12) C(11) -0.8(4) ? . . . . C(12) C(7) C(8) O(3) 179.1(2) ? . . . . C(12) C(7) C(8) C(9) -2.5(4) ? . . . . O(3) C(8) C(9) C(10) -178.1(2) ? . . . . C(7) C(8) C(9) C(10) 3.4(4) ? . . . . C(8) C(9) C(10) C(11) -1.0(4) ? . . . . C(9) C(10) C(11) O(4) 178.8(2) ? . . . . C(9) C(10) C(11) C(12) -2.3(4) ? . . . . O(4) C(11) C(12) C(7) -177.9(2) ? . . . . C(10) C(11) C(12) C(7) 3.2(4) ? . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 Cu(1) O(4) 2.579(2) ? . 1_545 Cu(1) O(4) 2.579(2) ? . 2_676 O(1) O(4) 3.310(2) ? . 1_545 O(1) O(4) 3.183(2) ? . 2_676 O(2) O(4) 2.650(2) ? . 1_545 O(2) O(4) 3.495(3) ? . 2_576 O(2) C(1) 3.327(3) ? . 1_455 O(2) C(2) 3.503(3) ? . 1_455 O(2) C(10) 3.342(3) ? . 1_545 O(2) C(11) 3.412(3) ? . 1_545 O(3) C(2) 3.312(4) ? . 1_455 O(3) C(9) 3.523(3) ? . 2_577 O(4) Cu(1) 2.579(2) ? . 1_565 O(4) O(1) 3.310(2) ? . 1_565 O(4) O(1) 3.183(2) ? . 2_676 O(4) O(2) 2.650(2) ? . 1_565 O(4) O(2) 3.495(3) ? . 2_576 O(4) O(4) 3.328(2) ? . 2_586 O(4) N(1) 3.355(3) ? . 1_565 O(4) N(1) 3.153(2) ? . 2_676 O(4) C(1) 3.170(3) ? . 2_676 O(4) C(5) 3.322(3) ? . 1_565 O(4) C(6) 3.346(3) ? . 1_565 N(1) O(4) 3.355(3) ? . 1_545 N(1) O(4) 3.153(2) ? . 2_676 C(1) O(2) 3.327(3) ? . 1_655 C(1) O(4) 3.170(3) ? . 2_676 C(2) O(2) 3.503(3) ? . 1_655 C(2) O(3) 3.312(4) ? . 1_655 C(4) C(9) 3.383(3) ? . 1_645 C(4) C(10) 3.506(3) ? . 1_645 C(5) O(4) 3.322(3) ? . 1_545 C(5) C(10) 3.431(4) ? . 1_545 C(5) C(10) 3.483(4) ? . 1_645 C(5) C(11) 3.423(4) ? . 1_545 C(6) O(4) 3.346(3) ? . 1_545 C(9) O(3) 3.523(3) ? . 2_577 C(9) C(4) 3.383(3) ? . 1_465 C(10) O(2) 3.342(3) ? . 1_565 C(10) C(4) 3.506(3) ? . 1_465 C(10) C(5) 3.483(4) ? . 1_465 C(10) C(5) 3.431(4) ? . 1_565 C(11) O(2) 3.412(3) ? . 1_565 C(11) C(5) 3.423(4) ? . 1_565 Cu(1) H(2) 2.59(3) ? . 1_545 Cu(1) H(2) 2.59(3) ? . 2_676 O(1) H(2) 2.85(3) ? . 1_545 O(2) H(2) 1.88(3) ? . 1_545 O(2) H(3) 3.079 ? . 1_455 O(2) H(4) 3.397 ? . 1_455 O(2) H(8) 2.670 ? . 1_545 O(3) H(4) 2.579 ? . 1_455 O(3) H(5) 2.968 ? . 2_567 O(3) H(7) 2.866 ? . 2_577 O(4) H(2) 3.01(3) ? . 2_586 O(4) H(3) 2.625 ? . 2_676 O(4) H(6) 2.861 ? . 1_565 N(1) H(2) 3.19(3) ? . 1_545 N(1) H(2) 3.34(2) ? . 2_676 N(1) H(8) 3.505 ? . 1_645 C(1) H(1) 3.51(4) ? . 1_655 C(1) H(8) 3.306 ? . 1_645 C(2) H(1) 3.00(3) ? . 1_655 C(2) H(8) 3.135 ? . 1_645 C(3) H(7) 3.465 ? . 1_645 C(3) H(8) 3.166 ? . 1_645 C(4) H(7) 3.129 ? . 1_645 C(4) H(8) 3.597 ? . 1_545 C(4) H(8) 3.334 ? . 1_645 C(5) H(2) 3.27(3) ? . 1_545 C(5) H(8) 3.278 ? . 1_545 C(5) H(8) 3.474 ? . 1_645 C(6) H(2) 2.66(3) ? . 1_545 C(6) H(9) 3.482 ? . 2_576 C(7) H(9) 3.457 ? . 2_576 C(8) H(4) 3.522 ? . 1_455 C(8) H(7) 3.330 ? . 2_577 C(9) H(5) 3.398 ? . 1_465 C(9) H(7) 3.309 ? . 2_577 C(10) H(6) 2.935 ? . 1_565 C(11) H(3) 3.464 ? . 2_676 C(11) H(6) 2.744 ? . 1_565 C(12) H(3) 3.396 ? . 2_676 C(12) H(6) 3.385 ? . 1_565 H(1) C(1) 3.51(4) ? . 1_455 H(1) C(2) 3.00(3) ? . 1_455 H(1) H(2) 3.58(4) ? . 1_545 H(1) H(3) 3.400 ? . 1_455 H(1) H(4) 2.452 ? . 1_455 H(1) H(5) 3.181 ? . 2_567 H(1) H(7) 3.379 ? . 2_577 H(1) H(8) 3.184 ? . 1_545 H(2) Cu(1) 2.59(3) ? . 1_565 H(2) O(1) 2.85(3) ? . 1_565 H(2) O(2) 1.88(3) ? . 1_565 H(2) O(4) 3.01(3) ? . 2_586 H(2) N(1) 3.19(3) ? . 1_565 H(2) N(1) 3.34(2) ? . 2_676 H(2) C(5) 3.27(3) ? . 1_565 H(2) C(6) 2.66(3) ? . 1_565 H(2) H(1) 3.58(4) ? . 1_565 H(2) H(2) 2.89(4) ? . 2_586 H(2) H(3) 3.572 ? . 1_465 H(2) H(3) 3.217 ? . 2_676 H(2) H(6) 3.014 ? . 1_565 H(3) O(2) 3.079 ? . 1_655 H(3) O(4) 2.625 ? . 2_676 H(3) C(11) 3.464 ? . 2_676 H(3) C(12) 3.396 ? . 2_676 H(3) H(1) 3.400 ? . 1_655 H(3) H(2) 3.572 ? . 1_645 H(3) H(2) 3.217 ? . 2_676 H(3) H(9) 2.722 ? . 2_676 H(4) O(2) 3.397 ? . 1_655 H(4) O(3) 2.579 ? . 1_655 H(4) C(8) 3.522 ? . 1_655 H(4) H(1) 2.452 ? . 1_655 H(4) H(7) 3.413 ? . 2_577 H(4) H(8) 3.533 ? . 1_645 H(5) O(3) 2.968 ? . 2_567 H(5) C(9) 3.398 ? . 1_645 H(5) H(1) 3.181 ? . 2_567 H(5) H(7) 2.996 ? . 1_645 H(5) H(8) 3.584 ? . 1_545 H(6) O(4) 2.861 ? . 1_545 H(6) C(10) 2.935 ? . 1_545 H(6) C(11) 2.744 ? . 1_545 H(6) C(12) 3.385 ? . 1_545 H(6) H(2) 3.014 ? . 1_545 H(6) H(8) 3.044 ? . 1_545 H(7) O(3) 2.866 ? . 2_577 H(7) C(3) 3.465 ? . 1_465 H(7) C(4) 3.129 ? . 1_465 H(7) C(8) 3.330 ? . 2_577 H(7) C(9) 3.309 ? . 2_577 H(7) H(1) 3.379 ? . 2_577 H(7) H(4) 3.413 ? . 2_577 H(7) H(5) 2.996 ? . 1_465 H(7) H(7) 2.912 ? . 2_577 H(8) O(2) 2.670 ? . 1_565 H(8) N(1) 3.505 ? . 1_465 H(8) C(1) 3.306 ? . 1_465 H(8) C(2) 3.135 ? . 1_465 H(8) C(3) 3.166 ? . 1_465 H(8) C(4) 3.334 ? . 1_465 H(8) C(4) 3.597 ? . 1_565 H(8) C(5) 3.474 ? . 1_465 H(8) C(5) 3.278 ? . 1_565 H(8) H(1) 3.184 ? . 1_565 H(8) H(4) 3.533 ? . 1_465 H(8) H(5) 3.584 ? . 1_565 H(8) H(6) 3.044 ? . 1_565 H(9) C(6) 3.482 ? . 2_576 H(9) C(7) 3.457 ? . 2_576 H(9) H(3) 2.722 ? . 2_676 H(9) H(9) 3.216 ? . 2_676 #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #============================================================================== #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #============================================================================== # Attachment '- 2assyn.cif' data_crystalclear _database_code_depnum_ccdc_archive 'CCDC 776334' #TrackingRef '- 2assyn.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C42 H34 Cu N2 O10' _chemical_formula_weight 790.25 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 23.078(9) _cell_length_b 11.080(4) _cell_length_c 15.594(6) _cell_angle_alpha 90.00 _cell_angle_beta 106.481(4) _cell_angle_gamma 90.00 _cell_volume 3824(2) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 55430 _cell_measurement_theta_min 3.10 _cell_measurement_theta_max 27.82 _exptl_crystal_description plate _exptl_crystal_colour green _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.373 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1636 _exptl_absorpt_coefficient_mu 0.633 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8839 _exptl_absorpt_correction_T_max 0.8839 _exptl_absorpt_process_details '(REQABA; Jacobson.,1998)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type CCD _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 55430 _diffrn_reflns_av_R_equivalents 0.0463 _diffrn_reflns_av_sigmaI/netI 0.0286 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.11 _diffrn_reflns_theta_max 27.50 _reflns_number_total 8750 _reflns_number_gt 7529 _reflns_threshold_expression >2sigma(I) _computing_data_collection crystalclear _computing_cell_refinement crystalclear _computing_data_reduction texsan _computing_structure_solution SIR-2004 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Non-coordinated solvent molecules were treated as isotropic models. ; _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^)+(0.1038P)^2^+3.3065P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8750 _refine_ls_number_parameters 465 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0764 _refine_ls_R_factor_gt 0.0655 _refine_ls_wR_factor_ref 0.1932 _refine_ls_wR_factor_gt 0.1832 _refine_ls_goodness_of_fit_ref 1.125 _refine_ls_restrained_S_all 1.125 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.5000 0.11547(4) 0.7500 0.02352(15) Uani 1 2 d S . . Cu2 Cu 0.0000 0.18521(4) 0.2500 0.02238(14) Uani 1 2 d S . . N1 N 0.0000 1.0045(3) 0.2500 0.0195(6) Uani 1 2 d S . . C1 C 0.5000 0.5473(3) 0.7500 0.0207(7) Uani 1 2 d S . . C2 C 0.0000 0.6169(3) 0.2500 0.0191(7) Uani 1 2 d S . . O1 O 0.41930(8) 0.11821(16) 0.76821(13) 0.0267(4) Uani 1 1 d . . . N2 N 0.5000 0.2953(3) 0.7500 0.0230(6) Uani 1 2 d S . . O2 O 0.08014(8) 0.18260(17) 0.23129(13) 0.0271(4) Uani 1 1 d . . . N3 N 0.5000 0.9348(3) 0.7500 0.0199(6) Uani 1 2 d S . . N4 N 0.0000 0.3664(3) 0.2500 0.0241(6) Uani 1 2 d S . . O3 O 0.44287(9) 0.1179(2) 0.58380(13) 0.0349(5) Uani 1 1 d . . . O4 O 0.05654(10) 0.1983(2) 0.41524(13) 0.0374(5) Uani 1 1 d . . . C3 C 0.5000 0.6824(3) 0.7500 0.0202(7) Uani 1 2 d S . . C4 C 0.54133(12) 0.8725(2) 0.81265(17) 0.0227(5) Uani 1 1 d . . . H1 H 0.5704 0.9153 0.8565 0.027 Uiso 1 1 calc R . . O5 O 0.44728(10) 0.1647(3) 0.91313(16) 0.0465(6) Uani 1 1 d . . . O6 O 0.05242(10) 0.1415(3) 0.08543(15) 0.0458(6) Uani 1 1 d . . . O7 O 0.13147(10) 0.1023(2) 0.00393(14) 0.0422(6) Uani 1 1 d . . . C5 C 0.04351(12) 0.8173(2) 0.31326(17) 0.0225(5) Uani 1 1 d . . . H2 H 0.0733 0.7765 0.3575 0.027 Uiso 1 1 calc R . . C6 C 0.0000 0.7528(3) 0.2500 0.0211(7) Uani 1 2 d S . . O8 O 0.36970(10) 0.2166(2) 0.99325(14) 0.0431(6) Uani 1 1 d . . . C7 C 0.04258(11) 0.9420(2) 0.31064(17) 0.0235(5) Uani 1 1 d . . . H3 H 0.0728 0.9848 0.3528 0.028 Uiso 1 1 calc R . . C8 C 0.30009(12) 0.1862(2) 0.75181(18) 0.0246(5) Uani 1 1 d . . . H4 H 0.3109 0.1662 0.6998 0.030 Uiso 1 1 calc R . . C9 C 0.54241(12) 0.7477(2) 0.81462(17) 0.0236(5) Uani 1 1 d . . . H5 H 0.5718 0.7070 0.8596 0.028 Uiso 1 1 calc R . . C10 C 0.34462(11) 0.1853(2) 0.83384(18) 0.0240(5) Uani 1 1 d . . . C11 C 0.15617(12) 0.1353(2) 0.16301(18) 0.0246(5) Uani 1 1 d . . . C12 C 0.20113(11) 0.1406(2) 0.24545(17) 0.0237(5) Uani 1 1 d . . . H6 H 0.1898 0.1572 0.2976 0.028 Uiso 1 1 calc R . . C13 C 0.10046(12) 0.2017(3) 0.49516(18) 0.0269(6) Uani 1 1 d . . . C14 C 0.39963(12) 0.1223(2) 0.50349(18) 0.0252(5) Uani 1 1 d . . . C15 C 0.17281(13) 0.1110(3) 0.08535(18) 0.0292(6) Uani 1 1 d . . . C16 C 0.15905(13) 0.2332(3) 0.49622(19) 0.0317(6) Uani 1 1 d . . . H7 H 0.1680 0.2505 0.4423 0.038 Uiso 1 1 calc R . . C17 C 0.40812(12) 0.1533(2) 0.83865(19) 0.0273(6) Uani 1 1 d . . . C18 C 0.26154(12) 0.1222(2) 0.25214(17) 0.0245(5) Uani 1 1 d . . . C19 C 0.05169(12) 0.5529(3) 0.2916(2) 0.0335(7) Uani 1 1 d . . . H8 H 0.0877 0.5936 0.3206 0.040 Uiso 1 1 calc R . . C20 C 0.09158(12) 0.1547(2) 0.15920(19) 0.0271(6) Uani 1 1 d . . . C21 C 0.34037(13) 0.0944(3) 0.49989(19) 0.0307(6) Uani 1 1 d . . . H9 H 0.3304 0.0755 0.5527 0.037 Uiso 1 1 calc R . . C22 C 0.44978(12) 0.4829(3) 0.7020(2) 0.0331(7) Uani 1 1 d . . . H10 H 0.4149 0.5236 0.6687 0.040 Uiso 1 1 calc R . . C23 C 0.41316(12) 0.1535(3) 0.4255(2) 0.0335(6) Uani 1 1 d . . . H11 H 0.4529 0.1745 0.4272 0.040 Uiso 1 1 calc R . . C24 C 0.24042(12) 0.2157(3) 0.74417(18) 0.0264(5) Uani 1 1 d . . . C25 C 0.36809(12) 0.1538(3) 0.34510(19) 0.0322(6) Uani 1 1 d . . . H12 H 0.3780 0.1746 0.2925 0.039 Uiso 1 1 calc R . . C26 C 0.32841(13) 0.2160(3) 0.91140(18) 0.0296(6) Uani 1 1 d . . . C27 C 0.20421(12) 0.2392(3) 0.57658(18) 0.0293(6) Uani 1 1 d . . . H13 H 0.2433 0.2628 0.5766 0.035 Uiso 1 1 calc R . . C28 C 0.29598(12) 0.0944(3) 0.41913(18) 0.0289(6) Uani 1 1 d . . . H14 H 0.2562 0.0737 0.4178 0.035 Uiso 1 1 calc R . . C29 C 0.13390(13) 0.1781(3) 0.6541(2) 0.0326(6) Uani 1 1 d . . . H15 H 0.1251 0.1585 0.7078 0.039 Uiso 1 1 calc R . . C30 C 0.19292(12) 0.2112(3) 0.65714(18) 0.0267(5) Uani 1 1 d . . . C31 C 0.08805(12) 0.1734(3) 0.57477(19) 0.0324(6) Uani 1 1 d . . . H16 H 0.0487 0.1511 0.5748 0.039 Uiso 1 1 calc R . . C32 C 0.22638(13) 0.2466(3) 0.82290(19) 0.0327(6) Uani 1 1 d . . . H17 H 0.1863 0.2673 0.8198 0.039 Uiso 1 1 calc R . . C33 C 0.30865(11) 0.1241(2) 0.33977(17) 0.0239(5) Uani 1 1 d . . . C34 C 0.45137(12) 0.3587(3) 0.7034(2) 0.0343(7) Uani 1 1 d . . . H18 H 0.4170 0.3162 0.6704 0.041 Uiso 1 1 calc R . . C35 C 0.26936(14) 0.2476(3) 0.90496(19) 0.0350(7) Uani 1 1 d . . . H19 H 0.2585 0.2697 0.9565 0.042 Uiso 1 1 calc R . . C36 C 0.27641(12) 0.0986(3) 0.17250(18) 0.0298(6) Uani 1 1 d . . . H20 H 0.3171 0.0859 0.1749 0.036 Uiso 1 1 calc R . . C37 C 0.23335(14) 0.0934(3) 0.09117(19) 0.0345(7) Uani 1 1 d . . . H21 H 0.2449 0.0780 0.0391 0.041 Uiso 1 1 calc R . . O9 O 0.1593(2) 0.5965(4) 0.4751(3) 0.1022(13) Uiso 1 1 d . . . C38 C 0.1627(3) 0.5669(5) 0.5506(4) 0.0808(14) Uiso 1 1 d . . . C39 C 0.2217(3) 0.5622(7) 0.6168(4) 0.107(2) Uiso 1 1 d . . . H22 H 0.2531 0.5654 0.5867 0.161 Uiso 1 1 calc R . . H23 H 0.2252 0.4876 0.6505 0.161 Uiso 1 1 calc R . . H24 H 0.2259 0.6303 0.6571 0.161 Uiso 1 1 calc R . . O10 O 0.3397(3) 0.5533(6) 0.0235(4) 0.154(2) Uiso 1 1 d . . . C40 C 0.2753(4) 0.5666(8) -0.1130(5) 0.134(3) Uiso 1 1 d . . . H25 H 0.2461 0.5576 -0.0793 0.201 Uiso 1 1 calc R . . H26 H 0.2663 0.5093 -0.1619 0.201 Uiso 1 1 calc R . . H27 H 0.2731 0.6480 -0.1366 0.201 Uiso 1 1 calc R . . C41 C 0.3369(4) 0.5437(7) -0.0534(5) 0.109(2) Uiso 1 1 d . . . C42 C 0.1073(4) 0.5385(8) 0.5715(5) 0.131(3) Uiso 1 1 d . . . H28 H 0.0732 0.5600 0.5213 0.196 Uiso 1 1 calc R . . H29 H 0.1054 0.5836 0.6239 0.196 Uiso 1 1 calc R . . H30 H 0.1061 0.4527 0.5833 0.196 Uiso 1 1 calc R . . C43 C 0.3886(5) 0.5187(10) -0.0775(7) 0.184(4) Uiso 1 1 d . . . H31 H 0.4234 0.5519 -0.0332 0.275 Uiso 1 1 calc R . . H32 H 0.3857 0.5545 -0.1354 0.275 Uiso 1 1 calc R . . H33 H 0.3933 0.4319 -0.0810 0.275 Uiso 1 1 calc R . . C44 C 0.04983(12) 0.4281(2) 0.2902(2) 0.0325(6) Uani 1 1 d . . . H34 H 0.0852 0.3852 0.3188 0.039 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0168(2) 0.0136(2) 0.0387(3) 0.000 0.00546(19) 0.000 Cu2 0.0161(2) 0.0141(2) 0.0351(3) 0.000 0.00418(18) 0.000 N1 0.0146(13) 0.0198(14) 0.0221(14) 0.000 0.0021(11) 0.000 C1 0.0192(16) 0.0161(15) 0.0238(17) 0.000 0.0010(13) 0.000 C2 0.0152(16) 0.0189(16) 0.0215(17) 0.000 0.0027(13) 0.000 O1 0.0162(9) 0.0226(9) 0.0395(11) -0.0028(8) 0.0049(8) 0.0008(7) N2 0.0133(13) 0.0171(14) 0.0340(17) 0.000 -0.0008(12) 0.000 O2 0.0180(9) 0.0249(10) 0.0370(11) -0.0017(8) 0.0053(8) 0.0005(7) N3 0.0145(13) 0.0158(13) 0.0286(15) 0.000 0.0047(11) 0.000 N4 0.0217(15) 0.0141(13) 0.0331(17) 0.000 0.0022(13) 0.000 O3 0.0283(11) 0.0432(12) 0.0251(10) 0.0057(8) -0.0055(8) -0.0044(8) O4 0.0286(11) 0.0515(14) 0.0247(10) -0.0020(9) -0.0046(8) -0.0014(9) C3 0.0215(17) 0.0150(16) 0.0221(17) 0.000 0.0029(14) 0.000 C4 0.0205(12) 0.0181(12) 0.0251(13) -0.0028(9) -0.0008(10) -0.0014(9) O5 0.0215(10) 0.0686(17) 0.0399(13) -0.0074(12) -0.0070(9) 0.0080(10) O6 0.0214(10) 0.0707(17) 0.0363(12) -0.0060(11) -0.0063(9) 0.0084(11) O7 0.0345(12) 0.0594(15) 0.0240(11) -0.0044(9) -0.0059(9) 0.0027(10) C5 0.0221(12) 0.0172(12) 0.0247(13) 0.0008(9) 0.0009(10) 0.0008(9) C6 0.0224(17) 0.0155(15) 0.0251(17) 0.000 0.0063(14) 0.000 O8 0.0377(12) 0.0599(15) 0.0237(10) -0.0035(10) -0.0044(9) 0.0049(11) C7 0.0223(12) 0.0192(12) 0.0249(12) -0.0016(9) 0.0000(10) 0.0004(9) C8 0.0211(12) 0.0265(13) 0.0254(13) -0.0028(10) 0.0053(10) 0.0009(9) C9 0.0240(12) 0.0174(11) 0.0247(12) 0.0001(9) -0.0009(10) 0.0021(9) C10 0.0181(12) 0.0243(13) 0.0266(13) -0.0007(10) 0.0014(10) 0.0012(9) C11 0.0189(12) 0.0249(12) 0.0278(13) -0.0003(10) 0.0031(10) 0.0005(10) C12 0.0196(12) 0.0288(13) 0.0216(12) -0.0018(10) 0.0040(10) 0.0026(10) C13 0.0205(12) 0.0293(13) 0.0260(13) -0.0034(10) -0.0011(10) 0.0018(10) C14 0.0196(12) 0.0261(13) 0.0258(13) -0.0001(10) -0.0001(10) -0.0007(9) C15 0.0284(14) 0.0322(15) 0.0224(13) -0.0020(10) -0.0003(11) 0.0019(11) C16 0.0276(14) 0.0407(16) 0.0264(14) 0.0017(12) 0.0070(11) 0.0009(12) C17 0.0189(12) 0.0237(13) 0.0345(15) -0.0002(11) 0.0000(11) 0.0012(10) C18 0.0207(13) 0.0285(13) 0.0226(13) -0.0004(10) 0.0033(10) 0.0029(10) C19 0.0203(13) 0.0210(13) 0.0499(18) -0.0016(12) -0.0052(12) -0.0025(10) C20 0.0190(12) 0.0230(12) 0.0351(15) 0.0017(11) 0.0010(11) 0.0018(10) C21 0.0263(14) 0.0408(16) 0.0245(14) 0.0044(11) 0.0063(11) -0.0036(11) C22 0.0225(13) 0.0206(13) 0.0456(17) 0.0020(11) -0.0075(12) 0.0020(10) C23 0.0167(12) 0.0501(18) 0.0321(15) 0.0015(13) 0.0041(11) -0.0021(12) C24 0.0202(12) 0.0326(14) 0.0245(13) 0.0002(10) 0.0035(10) 0.0019(10) C25 0.0214(13) 0.0529(18) 0.0231(13) 0.0023(12) 0.0077(11) -0.0017(12) C26 0.0277(14) 0.0331(14) 0.0232(13) -0.0011(11) -0.0002(11) -0.0006(11) C27 0.0176(12) 0.0405(16) 0.0290(14) 0.0002(12) 0.0053(10) -0.0023(11) C28 0.0182(12) 0.0390(15) 0.0275(14) 0.0032(11) 0.0033(11) -0.0014(11) C29 0.0222(13) 0.0481(18) 0.0277(14) 0.0026(12) 0.0074(11) -0.0004(12) C30 0.0185(12) 0.0335(14) 0.0257(13) -0.0010(11) 0.0025(10) 0.0042(10) C31 0.0185(13) 0.0460(17) 0.0303(14) 0.0010(12) 0.0033(11) -0.0017(11) C32 0.0232(13) 0.0439(17) 0.0308(14) -0.0026(12) 0.0075(11) 0.0066(12) C33 0.0176(12) 0.0291(13) 0.0225(13) 0.0004(10) 0.0018(10) 0.0026(9) C34 0.0223(14) 0.0194(13) 0.0510(18) -0.0006(12) -0.0061(13) -0.0012(10) C35 0.0322(15) 0.0467(18) 0.0264(14) -0.0045(13) 0.0086(12) 0.0024(13) C36 0.0219(13) 0.0397(16) 0.0277(14) -0.0027(11) 0.0067(11) 0.0031(11) C37 0.0348(16) 0.0431(17) 0.0256(14) -0.0019(12) 0.0085(12) 0.0055(13) C44 0.0221(13) 0.0172(12) 0.0488(18) 0.0009(11) -0.0052(12) 0.0015(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 Cu1 O1 1.962(2) 2_656 ? Cu1 O1 1.962(2) . ? Cu1 N2 1.992(3) . ? Cu1 N3 2.002(3) 1_545 ? Cu2 O2 1.953(2) 2 ? Cu2 O2 1.953(2) . ? Cu2 N1 2.002(3) 1_545 ? Cu2 N4 2.007(3) . ? N1 C7 1.346(3) 2 ? N1 C7 1.346(3) . ? N1 Cu2 2.002(3) 1_565 ? C1 C22 1.386(3) 2_656 ? C1 C22 1.386(3) . ? C1 C3 1.497(5) . ? C2 C19 1.381(3) . ? C2 C19 1.381(3) 2 ? C2 C6 1.507(5) . ? O1 C17 1.259(3) . ? N2 C34 1.349(3) 2_656 ? N2 C34 1.349(3) . ? O2 C20 1.264(3) . ? N3 C4 1.346(3) . ? N3 C4 1.346(3) 2_656 ? N3 Cu1 2.002(3) 1_565 ? N4 C44 1.332(3) 2 ? N4 C44 1.332(3) . ? O3 C14 1.363(3) . ? O4 C13 1.366(3) . ? C3 C9 1.392(3) 2_656 ? C3 C9 1.392(3) . ? C4 C9 1.384(4) . ? O5 C17 1.259(3) . ? O6 C20 1.254(3) . ? O7 C15 1.358(3) . ? C5 C7 1.382(4) . ? C5 C6 1.389(3) . ? C6 C5 1.389(3) 2 ? O8 C26 1.359(3) . ? C8 C24 1.387(4) . ? C8 C10 1.395(4) . ? C10 C26 1.405(4) . ? C10 C17 1.489(4) . ? C11 C15 1.397(4) . ? C11 C12 1.406(4) . ? C11 C20 1.490(4) . ? C12 C18 1.383(4) . ? C13 C31 1.387(4) . ? C13 C16 1.392(4) . ? C14 C23 1.382(4) . ? C14 C21 1.388(4) . ? C15 C37 1.388(4) . ? C16 C27 1.386(4) . ? C18 C36 1.404(4) . ? C18 C33 1.485(4) . ? C19 C44 1.383(4) . ? C21 C28 1.380(4) . ? C22 C34 1.376(4) . ? C23 C25 1.384(4) . ? C24 C32 1.398(4) . ? C24 C30 1.484(4) . ? C25 C33 1.390(4) . ? C26 C35 1.383(4) . ? C27 C30 1.389(4) . ? C28 C33 1.389(4) . ? C29 C31 1.382(4) . ? C29 C30 1.398(4) . ? C32 C35 1.379(4) . ? C36 C37 1.373(4) . ? O9 C38 1.203(6) . ? C38 C42 1.442(9) . ? C38 C39 1.457(8) . ? O10 C41 1.186(8) . ? C40 C41 1.484(9) . ? C41 C43 1.378(11) . ? 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 O1 Cu1 O1 178.23(11) 2_656 . ? O1 Cu1 N2 89.11(5) 2_656 . ? O1 Cu1 N2 89.11(5) . . ? O1 Cu1 N3 90.89(5) 2_656 1_545 ? O1 Cu1 N3 90.89(5) . 1_545 ? N2 Cu1 N3 180.000(1) . 1_545 ? O2 Cu2 O2 178.30(11) 2 . ? O2 Cu2 N1 89.15(5) 2 1_545 ? O2 Cu2 N1 89.15(5) . 1_545 ? O2 Cu2 N4 90.85(5) 2 . ? O2 Cu2 N4 90.85(5) . . ? N1 Cu2 N4 180.0 1_545 . ? C7 N1 C7 118.1(3) 2 . ? C7 N1 Cu2 120.94(15) 2 1_565 ? C7 N1 Cu2 120.94(15) . 1_565 ? C22 C1 C22 118.0(3) 2_656 . ? C22 C1 C3 121.01(17) 2_656 . ? C22 C1 C3 121.01(17) . . ? C19 C2 C19 118.3(3) . 2 ? C19 C2 C6 120.87(17) . . ? C19 C2 C6 120.87(17) 2 . ? C17 O1 Cu1 124.67(17) . . ? C34 N2 C34 117.2(3) 2_656 . ? C34 N2 Cu1 121.41(16) 2_656 . ? C34 N2 Cu1 121.41(16) . . ? C20 O2 Cu2 125.61(17) . . ? C4 N3 C4 118.4(3) . 2_656 ? C4 N3 Cu1 120.82(15) . 1_565 ? C4 N3 Cu1 120.82(15) 2_656 1_565 ? C44 N4 C44 118.2(3) 2 . ? C44 N4 Cu2 120.91(16) 2 . ? C44 N4 Cu2 120.91(16) . . ? C9 C3 C9 117.4(3) 2_656 . ? C9 C3 C1 121.31(16) 2_656 . ? C9 C3 C1 121.31(16) . . ? N3 C4 C9 122.2(2) . . ? C7 C5 C6 119.4(2) . . ? C5 C6 C5 118.1(3) 2 . ? C5 C6 C2 120.95(16) 2 . ? C5 C6 C2 120.95(16) . . ? N1 C7 C5 122.5(2) . . ? C24 C8 C10 122.4(2) . . ? C4 C9 C3 119.9(2) . . ? C8 C10 C26 118.7(2) . . ? C8 C10 C17 120.4(2) . . ? C26 C10 C17 120.9(2) . . ? C15 C11 C12 119.2(2) . . ? C15 C11 C20 120.7(2) . . ? C12 C11 C20 120.0(2) . . ? C18 C12 C11 122.0(2) . . ? O4 C13 C31 121.5(3) . . ? O4 C13 C16 119.0(3) . . ? C31 C13 C16 119.5(2) . . ? O3 C14 C23 121.9(2) . . ? O3 C14 C21 119.0(3) . . ? C23 C14 C21 119.1(2) . . ? O7 C15 C37 118.6(3) . . ? O7 C15 C11 122.1(3) . . ? C37 C15 C11 119.3(2) . . ? C27 C16 C13 120.1(3) . . ? O1 C17 O5 124.4(3) . . ? O1 C17 C10 118.2(2) . . ? O5 C17 C10 117.5(3) . . ? C12 C18 C36 117.1(2) . . ? C12 C18 C33 121.8(2) . . ? C36 C18 C33 121.2(2) . . ? C2 C19 C44 119.1(2) . . ? O6 C20 O2 124.5(3) . . ? O6 C20 C11 118.2(3) . . ? O2 C20 C11 117.3(2) . . ? C28 C21 C14 120.3(3) . . ? C34 C22 C1 119.5(3) . . ? C14 C23 C25 119.9(3) . . ? C8 C24 C32 117.0(2) . . ? C8 C24 C30 121.9(2) . . ? C32 C24 C30 121.1(2) . . ? C23 C25 C33 121.9(3) . . ? O8 C26 C35 118.7(3) . . ? O8 C26 C10 121.5(3) . . ? C35 C26 C10 119.7(2) . . ? C16 C27 C30 121.4(2) . . ? C21 C28 C33 121.6(3) . . ? C31 C29 C30 122.1(3) . . ? C27 C30 C29 117.3(2) . . ? C27 C30 C24 122.7(2) . . ? C29 C30 C24 120.0(2) . . ? C29 C31 C13 119.5(3) . . ? C35 C32 C24 122.1(3) . . ? C28 C33 C25 117.1(2) . . ? C28 C33 C18 122.1(2) . . ? C25 C33 C18 120.7(2) . . ? N2 C34 C22 123.0(3) . . ? C32 C35 C26 120.0(3) . . ? C37 C36 C18 122.0(3) . . ? C36 C37 C15 120.4(3) . . ? O9 C38 C42 117.7(6) . . ? O9 C38 C39 119.5(6) . . ? C42 C38 C39 122.8(6) . . ? O10 C41 C43 119.4(8) . . ? O10 C41 C40 112.7(8) . . ? C43 C41 C40 127.9(8) . . ? N4 C44 C19 122.7(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Cu1 O1 C17 -68.5(2) 2_656 . . . ? N2 Cu1 O1 C17 -68.6(2) . . . . ? N3 Cu1 O1 C17 111.4(2) 1_545 . . . ? O1 Cu1 N2 C34 -45.25(18) 2_656 . . 2_656 ? O1 Cu1 N2 C34 134.75(18) . . . 2_656 ? N3 Cu1 N2 C34 -111(100) 1_545 . . 2_656 ? O1 Cu1 N2 C34 134.75(18) 2_656 . . . ? O1 Cu1 N2 C34 -45.25(18) . . . . ? N3 Cu1 N2 C34 69(100) 1_545 . . . ? O2 Cu2 O2 C20 73.1(2) 2 . . . ? N1 Cu2 O2 C20 73.2(2) 1_545 . . . ? N4 Cu2 O2 C20 -106.8(2) . . . . ? O2 Cu2 N4 C44 -39.98(18) 2 . . 2 ? O2 Cu2 N4 C44 140.02(18) . . . 2 ? N1 Cu2 N4 C44 75(45) 1_545 . . 2 ? O2 Cu2 N4 C44 140.02(18) 2 . . . ? O2 Cu2 N4 C44 -39.98(18) . . . . ? N1 Cu2 N4 C44 -105(45) 1_545 . . . ? C22 C1 C3 C9 162.8(2) 2_656 . . 2_656 ? C22 C1 C3 C9 -17.2(2) . . . 2_656 ? C22 C1 C3 C9 -17.2(2) 2_656 . . . ? C22 C1 C3 C9 162.8(2) . . . . ? C4 N3 C4 C9 -0.20(19) 2_656 . . . ? Cu1 N3 C4 C9 179.80(19) 1_565 . . . ? C7 C5 C6 C5 -0.76(18) . . . 2 ? C7 C5 C6 C2 179.24(18) . . . . ? C19 C2 C6 C5 159.1(2) . . . 2 ? C19 C2 C6 C5 -20.9(2) 2 . . 2 ? C19 C2 C6 C5 -20.9(2) . . . . ? C19 C2 C6 C5 159.1(2) 2 . . . ? C7 N1 C7 C5 -0.81(19) 2 . . . ? Cu2 N1 C7 C5 179.19(19) 1_565 . . . ? C6 C5 C7 N1 1.6(4) . . . . ? N3 C4 C9 C3 0.4(4) . . . . ? C9 C3 C9 C4 -0.19(18) 2_656 . . . ? C1 C3 C9 C4 179.81(18) . . . . ? C24 C8 C10 C26 -0.4(4) . . . . ? C24 C8 C10 C17 -179.9(3) . . . . ? C15 C11 C12 C18 -0.1(4) . . . . ? C20 C11 C12 C18 179.5(2) . . . . ? C12 C11 C15 O7 178.7(3) . . . . ? C20 C11 C15 O7 -0.9(4) . . . . ? C12 C11 C15 C37 -0.5(4) . . . . ? C20 C11 C15 C37 179.9(3) . . . . ? O4 C13 C16 C27 178.9(3) . . . . ? C31 C13 C16 C27 -1.6(4) . . . . ? Cu1 O1 C17 O5 -17.3(4) . . . . ? Cu1 O1 C17 C10 161.87(18) . . . . ? C8 C10 C17 O1 -5.5(4) . . . . ? C26 C10 C17 O1 175.0(3) . . . . ? C8 C10 C17 O5 173.7(3) . . . . ? C26 C10 C17 O5 -5.8(4) . . . . ? C11 C12 C18 C36 0.4(4) . . . . ? C11 C12 C18 C33 -178.0(2) . . . . ? C19 C2 C19 C44 -0.1(2) 2 . . . ? C6 C2 C19 C44 179.9(2) . . . . ? Cu2 O2 C20 O6 10.8(4) . . . . ? Cu2 O2 C20 C11 -168.54(17) . . . . ? C15 C11 C20 O6 4.2(4) . . . . ? C12 C11 C20 O6 -175.4(3) . . . . ? C15 C11 C20 O2 -176.4(3) . . . . ? C12 C11 C20 O2 4.0(4) . . . . ? O3 C14 C21 C28 -177.9(3) . . . . ? C23 C14 C21 C28 2.0(5) . . . . ? C22 C1 C22 C34 -0.1(2) 2_656 . . . ? C3 C1 C22 C34 179.9(2) . . . . ? O3 C14 C23 C25 178.3(3) . . . . ? C21 C14 C23 C25 -1.5(5) . . . . ? C10 C8 C24 C32 0.9(4) . . . . ? C10 C8 C24 C30 -177.3(3) . . . . ? C14 C23 C25 C33 0.4(5) . . . . ? C8 C10 C26 O8 179.9(3) . . . . ? C17 C10 C26 O8 -0.6(4) . . . . ? C8 C10 C26 C35 -0.7(4) . . . . ? C17 C10 C26 C35 178.8(3) . . . . ? C13 C16 C27 C30 1.7(5) . . . . ? C14 C21 C28 C33 -1.2(5) . . . . ? C16 C27 C30 C29 -0.8(4) . . . . ? C16 C27 C30 C24 179.4(3) . . . . ? C31 C29 C30 C27 -0.2(5) . . . . ? C31 C29 C30 C24 179.6(3) . . . . ? C8 C24 C30 C27 -34.0(4) . . . . ? C32 C24 C30 C27 147.9(3) . . . . ? C8 C24 C30 C29 146.2(3) . . . . ? C32 C24 C30 C29 -31.9(4) . . . . ? C30 C29 C31 C13 0.2(5) . . . . ? O4 C13 C31 C29 -179.9(3) . . . . ? C16 C13 C31 C29 0.7(5) . . . . ? C8 C24 C32 C35 -0.3(5) . . . . ? C30 C24 C32 C35 177.9(3) . . . . ? C21 C28 C33 C25 0.1(4) . . . . ? C21 C28 C33 C18 178.9(3) . . . . ? C23 C25 C33 C28 0.3(5) . . . . ? C23 C25 C33 C18 -178.5(3) . . . . ? C12 C18 C33 C28 27.3(4) . . . . ? C36 C18 C33 C28 -151.1(3) . . . . ? C12 C18 C33 C25 -154.0(3) . . . . ? C36 C18 C33 C25 27.6(4) . . . . ? C34 N2 C34 C22 -0.1(2) 2_656 . . . ? Cu1 N2 C34 C22 179.9(2) . . . . ? C1 C22 C34 N2 0.2(5) . . . . ? C24 C32 C35 C26 -0.8(5) . . . . ? O8 C26 C35 C32 -179.4(3) . . . . ? C10 C26 C35 C32 1.3(5) . . . . ? C12 C18 C36 C37 -0.2(4) . . . . ? C33 C18 C36 C37 178.3(3) . . . . ? C18 C36 C37 C15 -0.4(5) . . . . ? O7 C15 C37 C36 -178.5(3) . . . . ? C11 C15 C37 C36 0.7(5) . . . . ? C44 N4 C44 C19 -0.1(2) 2 . . . ? Cu2 N4 C44 C19 179.9(2) . . . . ? C2 C19 C44 N4 0.1(5) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.848 _refine_diff_density_min -0.726 _refine_diff_density_rms 0.089