# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _publ_contact_author_name 'D Chan-Cheng Su' _publ_contact_author_address ; Chemistry National Taiwan Normal University No. 88, Sec. 4, Ting-Chow Rd Taipei City 11677 TAIWAN ; _publ_section_title ; Proton-Controllable Fluorescent Switch Based on Interconversion of Polynuclear and Dinuclear Copper(II) Complexes ; _publ_contact_author_email CCSU@NTNU.EDU.TW loop_ _publ_author_name 'Chan-Cheng Su' 'Chang-Chuan Chou' 'Yu-Hsin Hung' 'Hsueh-Ju Liu' # Attachment 'Complex 2(5921).cif' data_5921 _database_code_depnum_ccdc_archive 'CCDC 618879' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C40 H36 Cl0 Cu2 N8 O6' _chemical_formula_sum 'C40 H36 Cl0 Cu2 N8 O6' _chemical_formula_weight 851.85 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.6029(2) _cell_length_b 23.2657(4) _cell_length_c 16.6550(3) _cell_angle_alpha 90.00 _cell_angle_beta 108.0350(10) _cell_angle_gamma 90.00 _cell_volume 4275.11(13) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 32370 _cell_measurement_theta_min 2.037 _cell_measurement_theta_max 25.35 _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.324 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1752 _exptl_absorpt_coefficient_mu 1.047 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7043 _exptl_absorpt_correction_T_max 0.7843 _exptl_absorpt_process_details ; ? ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25181 _diffrn_reflns_av_R_equivalents 0.0537 _diffrn_reflns_av_sigmaI/netI 0.0493 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 25.34 _reflns_number_total 7539 _reflns_number_gt 5870 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 19' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1703P)^2^+15.7156P] 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 fixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7539 _refine_ls_number_parameters 505 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0771 _refine_ls_R_factor_gt 0.0597 _refine_ls_wR_factor_ref 0.1953 _refine_ls_wR_factor_gt 0.1757 _refine_ls_goodness_of_fit_ref 0.736 _refine_ls_restrained_S_all 0.736 _refine_ls_shift/su_max 0.095 _refine_ls_shift/su_mean 0.016 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 0.11124(5) 0.17238(2) 0.15462(3) 0.03230(18) Uani 1 1 d . . . Cu2 Cu 0.54076(5) 0.11950(2) 0.23772(3) 0.03305(19) Uani 1 1 d . . . O1 O 0.1248(3) 0.05221(15) 0.3415(2) 0.0502(9) Uani 1 1 d . . . O2 O 0.2719(4) 0.27054(16) 0.0106(3) 0.0608(11) Uani 1 1 d . . . O3 O 0.4057(3) -0.02393(13) 0.0952(2) 0.0461(8) Uani 1 1 d . . . O4 O 0.5116(3) 0.28257(13) 0.3310(2) 0.0466(9) Uani 1 1 d . . . O5 O 0.2947(7) 0.4456(3) 0.2066(3) 0.119(2) Uani 1 1 d . . . H5A H 0.3788 0.4435 0.2102 0.143 Uiso 1 1 d R . . H5B H 0.2713 0.4435 0.2570 0.143 Uiso 1 1 d R . . O6 O 0.4892(11) 0.3794(3) 0.2271(5) 0.163(4) Uani 1 1 d . . . H6A H 0.5643 0.3748 0.2717 0.196 Uiso 1 1 d R . . H6B H 0.4136 0.3748 0.2385 0.196 Uiso 1 1 d R . . N1 N 0.0947(3) 0.10732(15) 0.2229(2) 0.0344(8) Uani 1 1 d . . . N2 N 0.0165(3) 0.12219(16) 0.0589(2) 0.0351(8) Uani 1 1 d . . . N3 N 0.0822(4) 0.23899(16) 0.2220(2) 0.0385(9) Uani 1 1 d . . . N4 N 0.1927(4) 0.22918(15) 0.1062(2) 0.0369(9) Uani 1 1 d . . . N5 N 0.4738(4) 0.04531(15) 0.1960(2) 0.0387(9) Uani 1 1 d . . . N6 N 0.5867(4) 0.07999(16) 0.3502(2) 0.0378(9) Uani 1 1 d . . . N7 N 0.6120(3) 0.14658(16) 0.1485(2) 0.0352(8) Uani 1 1 d . . . N8 N 0.5419(4) 0.20071(15) 0.2642(2) 0.0355(8) Uani 1 1 d . . . C1 C -0.0004(5) 0.0669(2) 0.1781(3) 0.0430(11) Uani 1 1 d . . . H1A H 0.0286 0.0283 0.1919 0.052 Uiso 1 1 d R . . H1B H -0.0713 0.0728 0.1952 0.052 Uiso 1 1 d R . . C2 C -0.0305(4) 0.07542(19) 0.0847(3) 0.0364(10) Uani 1 1 d . . . C3 C -0.1052(5) 0.0381(2) 0.0270(3) 0.0462(12) Uani 1 1 d . . . H3 H -0.1395 0.0053 0.0460 0.055 Uiso 1 1 d R . . C4 C -0.1326(5) 0.0493(3) -0.0569(4) 0.0527(14) Uani 1 1 d . . . H4 H -0.1847 0.0230 -0.0962 0.063 Uiso 1 1 d R . . C5 C -0.0845(5) 0.0971(3) -0.0831(3) 0.0512(13) Uani 1 1 d . . . H5 H -0.1003 0.1047 -0.1422 0.061 Uiso 1 1 d R . . C6 C -0.0118(4) 0.1332(2) -0.0246(3) 0.0419(11) Uani 1 1 d . . . H6 H 0.0187 0.1673 -0.0434 0.050 Uiso 1 1 d R . . C7 C 0.0213(6) 0.2380(2) 0.2793(4) 0.0557(14) Uani 1 1 d . . . H7 H -0.0103 0.2019 0.2911 0.067 Uiso 1 1 d R . . C8 C 0.0055(7) 0.2869(3) 0.3212(4) 0.0663(17) Uani 1 1 d . . . H8 H -0.0408 0.2852 0.3599 0.080 Uiso 1 1 d R . . C9 C 0.0545(6) 0.3392(2) 0.3037(4) 0.0641(17) Uani 1 1 d . . . H9 H 0.0474 0.3730 0.3348 0.077 Uiso 1 1 d R . . C10 C 0.1132(6) 0.3395(2) 0.2448(4) 0.0542(14) Uani 1 1 d . . . H10 H 0.1462 0.3746 0.2309 0.065 Uiso 1 1 d R . . C11 C 0.1259(5) 0.28896(19) 0.2036(3) 0.0406(11) Uani 1 1 d . . . C12 C 0.1891(5) 0.28791(19) 0.1381(3) 0.0439(12) Uani 1 1 d . . . H12A H 0.2701 0.3022 0.1623 0.053 Uiso 1 1 d R . . H12B H 0.1458 0.3121 0.0920 0.053 Uiso 1 1 d R . . C13 C 0.2451(5) 0.2266(2) 0.0452(3) 0.0396(11) Uani 1 1 d . . . C14 C 0.2769(4) 0.16883(19) 0.0180(3) 0.0358(10) Uani 1 1 d . . . C15 C 0.2740(5) 0.1598(2) -0.0645(3) 0.0491(13) Uani 1 1 d . . . H15 H 0.2451 0.1899 -0.1052 0.059 Uiso 1 1 d R . . C16 C 0.3115(5) 0.1084(3) -0.0891(3) 0.0539(14) Uani 1 1 d . . . H16 H 0.3048 0.1028 -0.1474 0.065 Uiso 1 1 d R . . C17 C 0.3555(5) 0.0651(2) -0.0305(3) 0.0444(12) Uani 1 1 d . . . H17 H 0.3840 0.0296 -0.0468 0.053 Uiso 1 1 d R . . C18 C 0.3622(4) 0.07328(19) 0.0538(3) 0.0335(9) Uani 1 1 d . . . C19 C 0.3207(4) 0.12494(18) 0.0766(3) 0.0340(10) Uani 1 1 d . . . H19 H 0.3207 0.1295 0.1339 0.041 Uiso 1 1 d R . . C20 C 0.4166(4) 0.02718(19) 0.1176(3) 0.0339(10) Uani 1 1 d . . . C21 C 0.5113(6) -0.0010(2) 0.2575(3) 0.0519(14) Uani 1 1 d . . . H21A H 0.4417 -0.0239 0.2559 0.062 Uiso 1 1 d R . . H21B H 0.5698 -0.0245 0.2429 0.062 Uiso 1 1 d R . . C22 C 0.5646(5) 0.0229(2) 0.3437(3) 0.0444(12) Uani 1 1 d . . . C23 C 0.5967(7) -0.0114(2) 0.4155(4) 0.0628(17) Uani 1 1 d . . . H23 H 0.5791 -0.0518 0.4111 0.075 Uiso 1 1 d R . . C24 C 0.6508(7) 0.0127(3) 0.4932(4) 0.0687(18) Uani 1 1 d . . . H24 H 0.6699 -0.0103 0.5434 0.082 Uiso 1 1 d R . . C25 C 0.6747(6) 0.0710(3) 0.4989(4) 0.0595(15) Uani 1 1 d . . . H25 H 0.7171 0.0880 0.5524 0.071 Uiso 1 1 d R . . C26 C 0.6398(5) 0.1034(2) 0.4259(3) 0.0463(12) Uani 1 1 d . . . H26 H 0.6544 0.1441 0.4300 0.056 Uiso 1 1 d R . . C27 C 0.6355(5) 0.1156(2) 0.0868(3) 0.0434(12) Uani 1 1 d . . . H27 H 0.6183 0.0751 0.0822 0.052 Uiso 1 1 d R . . C28 C 0.6809(5) 0.1389(2) 0.0282(4) 0.0502(13) Uani 1 1 d . . . H28 H 0.6949 0.1152 -0.0150 0.060 Uiso 1 1 d R . . C29 C 0.7089(6) 0.1971(3) 0.0332(4) 0.0623(16) Uani 1 1 d . . . H29 H 0.7409 0.2142 -0.0079 0.075 Uiso 1 1 d R . . C30 C 0.6873(6) 0.2287(2) 0.0968(4) 0.0602(16) Uani 1 1 d . . . H30 H 0.7085 0.2687 0.1026 0.072 Uiso 1 1 d R . . C31 C 0.6375(5) 0.2031(2) 0.1533(3) 0.0431(12) Uani 1 1 d . . . C32 C 0.6088(6) 0.2362(2) 0.2211(4) 0.0533(14) Uani 1 1 d . . . H32A H 0.5610 0.2692 0.1970 0.064 Uiso 1 1 d R . . H32B H 0.6832 0.2484 0.2616 0.064 Uiso 1 1 d R . . C33 C 0.4962(4) 0.22982(19) 0.3160(3) 0.0351(10) Uani 1 1 d . . . C34 C 0.4191(4) 0.19773(18) 0.3588(3) 0.0327(9) Uani 1 1 d . . . C35 C 0.4358(5) 0.2063(2) 0.4447(3) 0.0412(11) Uani 1 1 d . . . H35 H 0.4968 0.2330 0.4753 0.049 Uiso 1 1 d R . . C36 C 0.3636(5) 0.1770(2) 0.4835(3) 0.0435(12) Uani 1 1 d . . . H36 H 0.3756 0.1817 0.5428 0.052 Uiso 1 1 d R . . C37 C 0.2730(4) 0.1404(2) 0.4382(3) 0.0396(11) Uani 1 1 d . . . H37 H 0.2243 0.1198 0.4659 0.048 Uiso 1 1 d R . . C38 C 0.2524(4) 0.13315(18) 0.3519(3) 0.0322(9) Uani 1 1 d . . . C39 C 0.3278(4) 0.16066(17) 0.3139(3) 0.0311(9) Uani 1 1 d . . . H39 H 0.3142 0.1543 0.2547 0.037 Uiso 1 1 d R . . C40 C 0.1510(4) 0.09416(19) 0.3036(3) 0.0356(10) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0405(3) 0.0263(3) 0.0289(3) 0.0007(2) 0.0090(2) 0.0004(2) Cu2 0.0433(3) 0.0220(3) 0.0332(3) -0.0019(2) 0.0109(3) -0.0028(2) O1 0.063(2) 0.046(2) 0.038(2) 0.0100(15) 0.0096(17) -0.0142(17) O2 0.084(3) 0.041(2) 0.069(3) 0.0158(18) 0.041(2) 0.0060(19) O3 0.054(2) 0.0272(16) 0.051(2) -0.0090(14) 0.0084(17) -0.0021(15) O4 0.072(2) 0.0260(16) 0.044(2) -0.0085(14) 0.0219(18) -0.0099(15) O5 0.168(6) 0.110(5) 0.061(3) 0.009(3) 0.010(4) -0.061(4) O6 0.279(11) 0.089(5) 0.133(6) 0.022(4) 0.082(7) 0.050(6) N1 0.037(2) 0.0307(18) 0.034(2) 0.0028(15) 0.0101(17) -0.0032(16) N2 0.037(2) 0.036(2) 0.029(2) -0.0018(15) 0.0047(17) 0.0034(16) N3 0.050(2) 0.032(2) 0.034(2) -0.0023(16) 0.0133(19) 0.0057(17) N4 0.050(2) 0.0261(18) 0.034(2) 0.0007(15) 0.0108(18) 0.0024(16) N5 0.053(2) 0.0245(18) 0.034(2) 0.0005(15) 0.0065(19) -0.0029(17) N6 0.042(2) 0.0303(19) 0.037(2) 0.0005(16) 0.0068(18) 0.0042(16) N7 0.039(2) 0.0292(19) 0.038(2) -0.0040(16) 0.0126(18) -0.0027(16) N8 0.049(2) 0.0269(18) 0.032(2) -0.0043(15) 0.0161(18) -0.0103(16) C1 0.045(3) 0.037(3) 0.044(3) 0.002(2) 0.008(2) -0.009(2) C2 0.033(2) 0.035(2) 0.039(3) -0.0020(19) 0.008(2) 0.0008(19) C3 0.039(3) 0.046(3) 0.050(3) -0.008(2) 0.010(2) -0.008(2) C4 0.042(3) 0.062(3) 0.048(3) -0.017(3) 0.005(2) 0.000(3) C5 0.048(3) 0.065(3) 0.035(3) -0.009(2) 0.005(2) -0.002(3) C6 0.043(3) 0.047(3) 0.031(3) 0.000(2) 0.005(2) 0.005(2) C7 0.072(4) 0.048(3) 0.056(3) -0.003(3) 0.033(3) 0.005(3) C8 0.096(5) 0.057(4) 0.056(4) -0.007(3) 0.038(4) 0.015(3) C9 0.094(5) 0.044(3) 0.056(4) -0.010(3) 0.026(4) 0.014(3) C10 0.077(4) 0.030(2) 0.053(3) -0.005(2) 0.016(3) 0.006(3) C11 0.051(3) 0.028(2) 0.037(3) 0.0014(19) 0.004(2) 0.009(2) C12 0.058(3) 0.025(2) 0.048(3) 0.002(2) 0.016(3) 0.002(2) C13 0.046(3) 0.036(2) 0.037(3) 0.009(2) 0.015(2) 0.003(2) C14 0.033(2) 0.039(2) 0.037(3) 0.0031(19) 0.012(2) 0.0025(19) C15 0.051(3) 0.060(3) 0.040(3) 0.015(2) 0.020(2) 0.013(3) C16 0.058(3) 0.074(4) 0.030(3) -0.004(2) 0.014(3) 0.006(3) C17 0.050(3) 0.054(3) 0.030(3) -0.008(2) 0.014(2) 0.003(2) C18 0.033(2) 0.033(2) 0.034(2) -0.0059(18) 0.0087(19) -0.0055(18) C19 0.042(3) 0.034(2) 0.028(2) 0.0024(18) 0.013(2) -0.0004(19) C20 0.034(2) 0.032(2) 0.036(2) -0.0044(18) 0.011(2) -0.0011(18) C21 0.081(4) 0.024(2) 0.044(3) 0.003(2) 0.009(3) -0.002(2) C22 0.060(3) 0.030(2) 0.042(3) 0.005(2) 0.014(2) 0.003(2) C23 0.102(5) 0.032(3) 0.046(3) 0.009(2) 0.012(3) 0.010(3) C24 0.102(5) 0.056(4) 0.035(3) 0.012(3) 0.002(3) 0.019(3) C25 0.074(4) 0.054(3) 0.038(3) 0.000(2) -0.002(3) 0.015(3) C26 0.051(3) 0.038(3) 0.040(3) -0.003(2) 0.001(2) 0.010(2) C27 0.047(3) 0.036(3) 0.051(3) -0.013(2) 0.020(2) 0.000(2) C28 0.052(3) 0.052(3) 0.055(3) -0.013(3) 0.028(3) 0.000(2) C29 0.076(4) 0.057(3) 0.068(4) -0.010(3) 0.043(3) -0.014(3) C30 0.089(4) 0.041(3) 0.067(4) -0.009(3) 0.048(4) -0.019(3) C31 0.052(3) 0.032(2) 0.050(3) -0.009(2) 0.024(3) -0.010(2) C32 0.081(4) 0.035(3) 0.055(3) -0.008(2) 0.037(3) -0.015(3) C33 0.042(3) 0.030(2) 0.030(2) -0.0031(18) 0.007(2) -0.0015(19) C34 0.040(2) 0.027(2) 0.028(2) 0.0015(17) 0.0068(19) 0.0029(18) C35 0.054(3) 0.035(2) 0.035(3) -0.008(2) 0.014(2) -0.003(2) C36 0.059(3) 0.043(3) 0.026(2) 0.0004(19) 0.010(2) -0.001(2) C37 0.046(3) 0.041(3) 0.031(2) 0.004(2) 0.011(2) 0.000(2) C38 0.039(2) 0.030(2) 0.027(2) 0.0054(17) 0.0102(19) 0.0055(18) C39 0.039(2) 0.028(2) 0.023(2) -0.0033(16) 0.0056(19) 0.0020(18) C40 0.042(3) 0.034(2) 0.033(3) 0.0034(19) 0.015(2) -0.0009(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 Cu1 N4 1.939(4) . ? Cu1 N1 1.938(4) . ? Cu1 N2 2.007(4) . ? Cu1 N3 2.002(4) . ? Cu2 N5 1.932(4) . ? Cu2 N8 1.940(4) . ? Cu2 N6 2.005(4) . ? Cu2 N7 2.012(4) . ? O1 C40 1.250(5) . ? O2 C13 1.259(6) . ? O3 C20 1.241(5) . ? O4 C33 1.254(5) . ? O5 H5A 0.9601 . ? O5 H5B 0.9600 . ? O6 H6A 0.9599 . ? O6 H6B 0.9600 . ? N1 C40 1.336(6) . ? N1 C1 1.467(6) . ? N2 C2 1.346(6) . ? N2 C6 1.350(6) . ? N3 C7 1.353(7) . ? N3 C11 1.341(6) . ? N4 C13 1.337(6) . ? N4 C12 1.471(6) . ? N5 C20 1.337(6) . ? N5 C21 1.458(6) . ? N6 C26 1.337(6) . ? N6 C22 1.351(6) . ? N7 C31 1.344(6) . ? N7 C27 1.350(6) . ? N8 C33 1.328(6) . ? N8 C32 1.465(6) . ? C1 C2 1.499(7) . ? C1 H1A 0.9598 . ? C1 H1B 0.9600 . ? C2 C3 1.382(7) . ? C3 C4 1.360(8) . ? C3 H3 0.9600 . ? C4 C5 1.375(8) . ? C4 H4 0.9600 . ? C5 C6 1.362(7) . ? C5 H5 0.9600 . ? C6 H6 0.9602 . ? C7 C8 1.376(8) . ? C7 H7 0.9601 . ? C8 C9 1.410(9) . ? C8 H8 0.9600 . ? C9 C10 1.357(9) . ? C9 H9 0.9600 . ? C10 C11 1.391(7) . ? C10 H10 0.9600 . ? C11 C12 1.492(7) . ? C12 H12A 0.9599 . ? C12 H12B 0.9600 . ? C13 C14 1.501(6) . ? C14 C15 1.380(7) . ? C14 C19 1.396(6) . ? C15 C16 1.376(8) . ? C15 H15 0.9601 . ? C16 C17 1.387(8) . ? C16 H16 0.9600 . ? C17 C18 1.395(6) . ? C17 H17 0.9601 . ? C18 C19 1.390(6) . ? C18 C20 1.504(6) . ? C19 H19 0.9598 . ? C21 C22 1.485(7) . ? C21 H21A 0.9602 . ? C21 H21B 0.9598 . ? C22 C23 1.388(7) . ? C23 C24 1.371(8) . ? C23 H23 0.9599 . ? C24 C25 1.382(9) . ? C24 H24 0.9601 . ? C25 C26 1.381(8) . ? C25 H25 0.9600 . ? C26 H26 0.9600 . ? C27 C28 1.357(7) . ? C27 H27 0.9600 . ? C28 C29 1.389(8) . ? C28 H28 0.9599 . ? C29 C30 1.374(8) . ? C29 H29 0.9599 . ? C30 C31 1.383(7) . ? C30 H30 0.9598 . ? C31 C32 1.487(7) . ? C32 H32A 0.9600 . ? C32 H32B 0.9599 . ? C33 C34 1.505(6) . ? C34 C39 1.391(6) . ? C34 C35 1.397(6) . ? C35 C36 1.385(7) . ? C35 H35 0.9601 . ? C36 C37 1.381(7) . ? C36 H36 0.9600 . ? C37 C38 1.393(6) . ? C37 H37 0.9602 . ? C38 C39 1.386(6) . ? C38 C40 1.506(6) . ? C39 H39 0.9598 . ? 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 N4 Cu1 N1 157.75(16) . . ? N4 Cu1 N2 106.47(16) . . ? N1 Cu1 N2 83.24(16) . . ? N4 Cu1 N3 83.90(16) . . ? N1 Cu1 N3 102.23(16) . . ? N2 Cu1 N3 138.56(16) . . ? N5 Cu2 N8 157.83(17) . . ? N5 Cu2 N6 83.54(16) . . ? N8 Cu2 N6 104.65(16) . . ? N5 Cu2 N7 103.02(16) . . ? N8 Cu2 N7 83.55(15) . . ? N6 Cu2 N7 141.48(16) . . ? H5A O5 H5B 120.0 . . ? H6A O6 H6B 120.0 . . ? C40 N1 C1 114.9(4) . . ? C40 N1 Cu1 131.6(3) . . ? C1 N1 Cu1 113.5(3) . . ? C2 N2 C6 119.2(4) . . ? C2 N2 Cu1 113.1(3) . . ? C6 N2 Cu1 127.4(3) . . ? C7 N3 C11 119.5(4) . . ? C7 N3 Cu1 126.7(3) . . ? C11 N3 Cu1 113.7(3) . . ? C13 N4 C12 112.7(4) . . ? C13 N4 Cu1 132.8(3) . . ? C12 N4 Cu1 114.3(3) . . ? C20 N5 C21 113.8(4) . . ? C20 N5 Cu2 131.0(3) . . ? C21 N5 Cu2 114.1(3) . . ? C26 N6 C22 119.8(4) . . ? C26 N6 Cu2 127.3(3) . . ? C22 N6 Cu2 112.8(3) . . ? C31 N7 C27 118.4(4) . . ? C31 N7 Cu2 113.3(3) . . ? C27 N7 Cu2 128.3(3) . . ? C33 N8 C32 114.2(4) . . ? C33 N8 Cu2 132.0(3) . . ? C32 N8 Cu2 113.9(3) . . ? N1 C1 C2 109.8(4) . . ? N1 C1 H1A 109.0 . . ? C2 C1 H1A 108.9 . . ? N1 C1 H1B 109.6 . . ? C2 C1 H1B 110.0 . . ? H1A C1 H1B 109.5 . . ? N2 C2 C3 120.9(4) . . ? N2 C2 C1 116.9(4) . . ? C3 C2 C1 122.2(4) . . ? C4 C3 C2 119.5(5) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.4 . . ? C3 C4 C5 119.5(5) . . ? C3 C4 H4 118.4 . . ? C5 C4 H4 122.1 . . ? C6 C5 C4 119.6(5) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.4 . . ? N2 C6 C5 121.3(5) . . ? N2 C6 H6 119.7 . . ? C5 C6 H6 119.0 . . ? N3 C7 C8 121.6(5) . . ? N3 C7 H7 118.4 . . ? C8 C7 H7 120.0 . . ? C7 C8 C9 118.9(6) . . ? C7 C8 H8 119.8 . . ? C9 C8 H8 121.3 . . ? C10 C9 C8 118.6(5) . . ? C10 C9 H9 122.1 . . ? C8 C9 H9 119.2 . . ? C9 C10 C11 120.3(5) . . ? C9 C10 H10 120.4 . . ? C11 C10 H10 119.3 . . ? N3 C11 C10 121.0(5) . . ? N3 C11 C12 117.3(4) . . ? C10 C11 C12 121.7(5) . . ? N4 C12 C11 110.8(4) . . ? N4 C12 H12A 109.9 . . ? C11 C12 H12A 109.1 . . ? N4 C12 H12B 108.8 . . ? C11 C12 H12B 108.8 . . ? H12A C12 H12B 109.5 . . ? O2 C13 N4 123.1(4) . . ? O2 C13 C14 118.0(4) . . ? N4 C13 C14 118.8(4) . . ? C15 C14 C19 118.4(4) . . ? C15 C14 C13 120.4(4) . . ? C19 C14 C13 120.9(4) . . ? C14 C15 C16 121.0(5) . . ? C14 C15 H15 119.2 . . ? C16 C15 H15 119.8 . . ? C17 C16 C15 120.3(5) . . ? C17 C16 H16 120.7 . . ? C15 C16 H16 119.0 . . ? C16 C17 C18 120.1(5) . . ? C16 C17 H17 120.7 . . ? C18 C17 H17 119.1 . . ? C19 C18 C17 118.5(4) . . ? C19 C18 C20 121.9(4) . . ? C17 C18 C20 119.5(4) . . ? C18 C19 C14 121.6(4) . . ? C18 C19 H19 118.2 . . ? C14 C19 H19 120.2 . . ? O3 C20 N5 124.7(4) . . ? O3 C20 C18 119.3(4) . . ? N5 C20 C18 116.0(4) . . ? N5 C21 C22 110.3(4) . . ? N5 C21 H21A 109.0 . . ? C22 C21 H21A 109.2 . . ? N5 C21 H21B 108.8 . . ? C22 C21 H21B 110.0 . . ? H21A C21 H21B 109.5 . . ? N6 C22 C23 120.2(5) . . ? N6 C22 C21 117.2(4) . . ? C23 C22 C21 122.5(5) . . ? C24 C23 C22 120.0(5) . . ? C24 C23 H23 119.8 . . ? C22 C23 H23 120.2 . . ? C23 C24 C25 119.4(5) . . ? C23 C24 H24 120.7 . . ? C25 C24 H24 120.0 . . ? C24 C25 C26 118.5(5) . . ? C24 C25 H25 120.2 . . ? C26 C25 H25 121.2 . . ? N6 C26 C25 122.1(5) . . ? N6 C26 H26 119.3 . . ? C25 C26 H26 118.6 . . ? C28 C27 N7 123.3(5) . . ? C28 C27 H27 116.8 . . ? N7 C27 H27 119.9 . . ? C27 C28 C29 118.8(5) . . ? C27 C28 H28 120.3 . . ? C29 C28 H28 120.8 . . ? C30 C29 C28 118.2(5) . . ? C30 C29 H29 122.0 . . ? C28 C29 H29 119.8 . . ? C29 C30 C31 120.6(5) . . ? C29 C30 H30 119.7 . . ? C31 C30 H30 119.7 . . ? N7 C31 C30 120.7(4) . . ? N7 C31 C32 117.0(4) . . ? C30 C31 C32 122.2(4) . . ? N8 C32 C31 111.0(4) . . ? N8 C32 H32A 109.4 . . ? C31 C32 H32A 109.5 . . ? N8 C32 H32B 108.6 . . ? C31 C32 H32B 108.9 . . ? H32A C32 H32B 109.5 . . ? O4 C33 N8 124.6(4) . . ? O4 C33 C34 117.4(4) . . ? N8 C33 C34 118.0(4) . . ? C39 C34 C35 118.7(4) . . ? C39 C34 C33 121.2(4) . . ? C35 C34 C33 120.0(4) . . ? C36 C35 C34 119.6(5) . . ? C36 C35 H35 121.5 . . ? C34 C35 H35 118.8 . . ? C35 C36 C37 121.2(4) . . ? C35 C36 H36 120.5 . . ? C37 C36 H36 118.3 . . ? C36 C37 C38 119.7(4) . . ? C36 C37 H37 120.5 . . ? C38 C37 H37 119.8 . . ? C39 C38 C37 119.0(4) . . ? C39 C38 C40 122.2(4) . . ? C37 C38 C40 118.7(4) . . ? C34 C39 C38 121.6(4) . . ? C34 C39 H39 120.3 . . ? C38 C39 H39 118.1 . . ? O1 C40 N1 124.6(4) . . ? O1 C40 C38 118.1(4) . . ? N1 C40 C38 117.2(4) . . ? _diffrn_measured_fraction_theta_max 0.965 _diffrn_reflns_theta_full 25.34 _diffrn_measured_fraction_theta_full 0.965 _refine_diff_density_max 2.227 _refine_diff_density_min -0.669 _refine_diff_density_rms 0.179 # SQUEEZE RESULTS (APPEND TO CIF) #loop_ #_platon_squeeze_void_nr #_platon_squeeze_void_average_x #_platon_squeeze_void_average_y #_platon_squeeze_void_average_z #_platon_squeeze_void_volume #_platon_squeeze_void_count_electrons #1 0.000 1.000 0.500 344.0 55.9 #2 0.500 0.500 1.000 344.0 56.5 #_platon_squeeze_details #; ? #; data_6117 _database_code_depnum_ccdc_archive 'CCDC 620454' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C40 H36 Cl4 Cu2 N8 O20' _chemical_formula_sum 'C40 H36 Cl4 Cu2 N8 O20' _chemical_formula_weight 1217.65 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' Cu Cu 0.3201 1.2651 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/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 10.9020(7) _cell_length_b 17.764(2) _cell_length_c 15.5030(16) _cell_angle_alpha 90.00 _cell_angle_beta 110.58 _cell_angle_gamma 90.00 _cell_volume 2810.7(5) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 7425 _cell_measurement_theta_min 2.037 _cell_measurement_theta_max 25.35 _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.439 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1236 _exptl_absorpt_coefficient_mu 1.022 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11329 _diffrn_reflns_av_R_equivalents 0.1255 _diffrn_reflns_av_sigmaI/netI 0.1718 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 25.27 _reflns_number_total 4794 _reflns_number_gt 2309 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 19' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^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 fixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0011(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4794 _refine_ls_number_parameters 335 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1580 _refine_ls_R_factor_gt 0.0814 _refine_ls_wR_factor_ref 0.2676 _refine_ls_wR_factor_gt 0.2138 _refine_ls_goodness_of_fit_ref 0.759 _refine_ls_restrained_S_all 0.759 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.60224(8) 0.23811(6) 0.54966(6) 0.0332(4) Uani 1 1 d . . . Cl1 Cl 0.3797(2) 0.29561(15) 0.64238(19) 0.0575(7) Uani 1 1 d . . . Cl2 Cl 0.1932(2) 0.47139(14) 0.16055(16) 0.0474(6) Uani 1 1 d . . . O1 O 0.4348(5) 0.2156(3) 0.4517(4) 0.0385(14) Uani 1 1 d . . . O2 O -0.2221(5) 0.2459(3) 0.1428(4) 0.0412(15) Uani 1 1 d . . . O3 O 0.5119(6) 0.2653(4) 0.6594(5) 0.0566(18) Uani 1 1 d . . . O4 O 0.3357(7) 0.3341(4) 0.5544(5) 0.074(2) Uani 1 1 d . . . O5 O 0.2945(7) 0.2347(4) 0.6390(5) 0.071(2) Uani 1 1 d . . . O6 O 0.3870(9) 0.3454(5) 0.7169(7) 0.098(3) Uani 1 1 d . . . O7 O 0.0954(8) 0.4604(6) 0.2012(6) 0.102(3) Uani 1 1 d . . . O8 O 0.3075(8) 0.4322(5) 0.2145(6) 0.090(3) Uani 1 1 d . . . O9 O 0.2261(8) 0.5476(4) 0.1641(6) 0.089(3) Uani 1 1 d . . . O10 O 0.1492(11) 0.4442(7) 0.0690(6) 0.120(4) Uani 1 1 d . . . N1 N 0.6128(6) 0.3470(4) 0.5201(5) 0.0379(17) Uani 1 1 d . . . N2 N 0.3955(6) 0.3039(4) 0.3424(5) 0.0370(17) Uani 1 1 d . . . H2' H 0.3370 0.3312 0.3031 0.044 Uiso 1 1 calc R . . N3 N -0.0848(6) 0.3361(4) 0.1275(5) 0.0416(18) Uani 1 1 d . . . H3' H -0.0075 0.3553 0.1491 0.050 Uiso 1 1 calc R . . N4 N -0.3830(6) 0.3734(4) 0.0772(4) 0.0336(16) Uani 1 1 d . . . C1 C 0.6572(8) 0.3946(5) 0.5904(7) 0.046(2) Uani 1 1 d . . . H1 H 0.6686 0.3776 0.6495 0.055 Uiso 1 1 calc R . . C2 C 0.6876(10) 0.4701(6) 0.5784(8) 0.068(3) Uani 1 1 d . . . H2 H 0.7203 0.5023 0.6286 0.081 Uiso 1 1 calc R . . C3 C 0.6675(11) 0.4950(6) 0.4901(8) 0.070(3) Uani 1 1 d . . . H3 H 0.6871 0.5444 0.4797 0.084 Uiso 1 1 calc R . . C4 C 0.6182(8) 0.4456(6) 0.4176(7) 0.052(3) Uani 1 1 d . . . H4 H 0.6028 0.4618 0.3577 0.063 Uiso 1 1 calc R . . C5 C 0.5917(7) 0.3728(5) 0.4337(5) 0.038(2) Uani 1 1 d . . . C6 C 0.5344(7) 0.3179(5) 0.3563(6) 0.042(2) Uani 1 1 d . . . H6A H 0.5418 0.3380 0.3001 0.050 Uiso 1 1 calc R . . H6B H 0.5828 0.2710 0.3706 0.050 Uiso 1 1 calc R . . C7 C 0.3572(7) 0.2525(4) 0.3864(5) 0.0270(17) Uani 1 1 d . . . C8 C 0.2132(7) 0.2359(5) 0.3586(5) 0.0323(19) Uani 1 1 d . . . C9 C 0.1701(8) 0.1896(5) 0.4139(6) 0.045(2) Uani 1 1 d . . . H9 H 0.2307 0.1717 0.4687 0.054 Uiso 1 1 calc R . . C10 C 0.0438(8) 0.1697(6) 0.3910(6) 0.050(3) Uani 1 1 d . . . H10 H 0.0184 0.1367 0.4283 0.061 Uiso 1 1 calc R . . C11 C -0.0491(7) 0.1989(5) 0.3111(6) 0.043(2) Uani 1 1 d . . . H11 H -0.1369 0.1862 0.2961 0.052 Uiso 1 1 calc R . . C12 C -0.0116(8) 0.2463(5) 0.2542(6) 0.037(2) Uani 1 1 d . . . C13 C 0.1230(7) 0.2637(5) 0.2774(6) 0.040(2) Uani 1 1 d . . . H13 H 0.1508 0.2936 0.2385 0.048 Uiso 1 1 calc R . . C14 C -0.1104(7) 0.2767(5) 0.1704(6) 0.035(2) Uani 1 1 d . . . C15 C -0.1788(8) 0.3703(5) 0.0472(5) 0.041(2) Uani 1 1 d . . . H15A H -0.2206 0.3318 0.0021 0.049 Uiso 1 1 calc R . . H15B H -0.1346 0.4050 0.0196 0.049 Uiso 1 1 calc R . . C16 C -0.2834(7) 0.4129(5) 0.0739(5) 0.0332(19) Uani 1 1 d . . . C17 C -0.2670(9) 0.4881(5) 0.0958(6) 0.051(2) Uani 1 1 d . . . H17 H -0.1954 0.5146 0.0924 0.061 Uiso 1 1 calc R . . C18 C -0.3610(10) 0.5230(6) 0.1232(7) 0.055(3) Uani 1 1 d . . . H18 H -0.3537 0.5738 0.1385 0.066 Uiso 1 1 calc R . . C19 C -0.4648(9) 0.4817(6) 0.1272(6) 0.050(2) Uani 1 1 d . . . H19 H -0.5290 0.5043 0.1451 0.060 Uiso 1 1 calc R . . C20 C -0.4734(8) 0.4078(5) 0.1051(5) 0.037(2) Uani 1 1 d . . . H20 H -0.5433 0.3798 0.1091 0.044 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 0.0234(6) 0.0379(7) 0.0315(6) 0.0034(5) 0.0012(4) 0.0012(4) Cl1 0.0700(16) 0.0495(16) 0.0684(17) 0.0067(13) 0.0434(14) 0.0088(12) Cl2 0.0458(13) 0.0453(15) 0.0476(13) -0.0001(11) 0.0120(10) -0.0033(10) O1 0.025(3) 0.040(4) 0.041(3) 0.007(3) 0.001(3) -0.003(2) O2 0.030(3) 0.041(4) 0.040(3) 0.006(3) -0.002(3) -0.004(2) O3 0.062(4) 0.060(5) 0.053(4) -0.003(3) 0.027(3) 0.015(3) O4 0.075(5) 0.054(5) 0.097(6) 0.044(4) 0.034(4) 0.033(4) O5 0.082(5) 0.071(5) 0.070(5) 0.004(4) 0.039(4) -0.031(4) O6 0.119(7) 0.081(6) 0.122(8) -0.041(6) 0.075(7) -0.013(5) O7 0.070(5) 0.144(9) 0.108(7) -0.031(6) 0.050(5) -0.038(5) O8 0.082(6) 0.088(7) 0.095(6) 0.031(5) 0.028(5) 0.031(5) O9 0.091(6) 0.039(5) 0.127(7) 0.015(5) 0.027(5) 0.004(4) O10 0.156(9) 0.130(10) 0.054(5) -0.021(5) 0.013(6) -0.020(7) N1 0.029(4) 0.035(4) 0.044(4) -0.005(3) 0.006(3) -0.002(3) N2 0.026(3) 0.045(5) 0.036(4) 0.006(3) 0.005(3) 0.000(3) N3 0.029(4) 0.051(5) 0.041(4) 0.017(4) 0.008(3) -0.002(3) N4 0.019(3) 0.039(4) 0.032(4) 0.003(3) -0.004(3) 0.004(3) C1 0.036(5) 0.036(6) 0.055(6) 0.003(5) 0.001(4) 0.001(4) C2 0.055(6) 0.054(7) 0.076(8) -0.010(6) 0.001(6) -0.010(5) C3 0.073(7) 0.049(7) 0.076(8) 0.014(6) 0.014(6) -0.017(6) C4 0.036(5) 0.049(6) 0.066(7) 0.012(5) 0.010(5) -0.008(4) C5 0.018(4) 0.061(6) 0.027(4) 0.007(4) -0.003(3) -0.003(4) C6 0.032(4) 0.057(6) 0.036(5) 0.009(4) 0.012(4) -0.008(4) C7 0.029(4) 0.022(4) 0.024(4) 0.007(3) 0.002(3) 0.001(3) C8 0.027(4) 0.033(5) 0.036(5) -0.006(4) 0.010(4) -0.011(3) C9 0.034(5) 0.057(6) 0.042(5) 0.014(5) 0.011(4) 0.002(4) C10 0.042(5) 0.059(7) 0.049(6) 0.026(5) 0.015(4) -0.010(4) C11 0.019(4) 0.046(6) 0.058(6) 0.014(5) 0.004(4) -0.008(4) C12 0.031(4) 0.041(6) 0.032(4) 0.000(4) 0.004(4) 0.002(4) C13 0.024(4) 0.056(6) 0.032(4) 0.006(4) 0.001(4) 0.007(4) C14 0.029(5) 0.043(6) 0.033(4) 0.002(4) 0.010(4) 0.001(4) C15 0.039(5) 0.057(6) 0.018(4) 0.008(4) -0.001(3) -0.003(4) C16 0.025(4) 0.044(5) 0.029(4) 0.010(4) 0.008(3) 0.007(4) C17 0.052(6) 0.036(6) 0.056(6) 0.014(5) 0.007(5) 0.000(4) C18 0.068(7) 0.030(5) 0.062(6) 0.005(5) 0.019(5) 0.006(5) C19 0.046(5) 0.052(7) 0.053(6) -0.003(5) 0.021(5) 0.008(5) C20 0.034(4) 0.034(5) 0.039(5) -0.006(4) 0.009(4) 0.003(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 Cu1 O1 1.962(5) . ? Cu1 O2 1.973(5) 4_666 ? Cu1 N1 2.000(7) . ? Cu1 N4 2.021(7) 4_666 ? Cu1 O3 2.297(6) . ? Cl1 O5 1.415(7) . ? Cl1 O6 1.435(8) . ? Cl1 O4 1.448(7) . ? Cl1 O3 1.472(7) . ? Cl2 O9 1.398(8) . ? Cl2 O10 1.415(9) . ? Cl2 O8 1.416(8) . ? Cl2 O7 1.429(8) . ? O1 C7 1.252(9) . ? O2 C14 1.264(10) . ? O2 Cu1 1.973(5) 4_465 ? N1 C1 1.329(11) . ? N1 C5 1.357(10) . ? N2 C7 1.293(9) . ? N2 C6 1.474(10) . ? N2 H2' 0.8600 . ? N3 C14 1.329(11) . ? N3 C15 1.440(10) . ? N3 H3' 0.8600 . ? N4 C16 1.309(10) . ? N4 C20 1.354(10) . ? N4 Cu1 2.021(7) 4_465 ? C1 C2 1.409(14) . ? C1 H1 0.9300 . ? C2 C3 1.381(15) . ? C2 H2 0.9300 . ? C3 C4 1.377(15) . ? C3 H3 0.9300 . ? C4 C5 1.367(12) . ? C4 H4 0.9300 . ? C5 C6 1.501(12) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.504(10) . ? C8 C13 1.387(11) . ? C8 C9 1.384(11) . ? C9 C10 1.343(11) . ? C9 H9 0.9300 . ? C10 C11 1.395(12) . ? C10 H10 0.9300 . ? C11 C12 1.382(12) . ? C11 H11 0.9300 . ? C12 C13 1.418(11) . ? C12 C14 1.468(11) . ? C13 H13 0.9300 . ? C15 C16 1.542(11) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.373(12) . ? C17 C18 1.386(14) . ? C17 H17 0.9300 . ? C18 C19 1.369(13) . ? C18 H18 0.9300 . ? C19 C20 1.352(12) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? 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 O2 174.8(2) . 4_666 ? O1 Cu1 N1 97.6(3) . . ? O2 Cu1 N1 84.8(3) 4_666 . ? O1 Cu1 N4 86.9(2) . 4_666 ? O2 Cu1 N4 90.1(2) 4_666 4_666 ? N1 Cu1 N4 171.7(3) . 4_666 ? O1 Cu1 O3 95.3(2) . . ? O2 Cu1 O3 89.2(2) 4_666 . ? N1 Cu1 O3 92.3(3) . . ? N4 Cu1 O3 94.2(3) 4_666 . ? O5 Cl1 O6 110.5(5) . . ? O5 Cl1 O4 109.2(5) . . ? O6 Cl1 O4 112.0(6) . . ? O5 Cl1 O3 108.4(5) . . ? O6 Cl1 O3 107.9(5) . . ? O4 Cl1 O3 108.7(4) . . ? O9 Cl2 O10 111.2(6) . . ? O9 Cl2 O8 107.0(5) . . ? O10 Cl2 O8 110.0(6) . . ? O9 Cl2 O7 109.7(6) . . ? O10 Cl2 O7 110.7(6) . . ? O8 Cl2 O7 108.1(6) . . ? C7 O1 Cu1 134.3(5) . . ? C14 O2 Cu1 139.2(6) . 4_465 ? Cl1 O3 Cu1 126.3(4) . . ? C1 N1 C5 118.7(8) . . ? C1 N1 Cu1 117.5(6) . . ? C5 N1 Cu1 123.3(6) . . ? C7 N2 C6 123.2(7) . . ? C7 N2 H2' 118.4 . . ? C6 N2 H2' 118.4 . . ? C14 N3 C15 123.8(7) . . ? C14 N3 H3' 118.1 . . ? C15 N3 H3' 118.1 . . ? C16 N4 C20 118.5(7) . . ? C16 N4 Cu1 121.6(5) . 4_465 ? C20 N4 Cu1 119.8(5) . 4_465 ? N1 C1 C2 122.1(9) . . ? N1 C1 H1 118.9 . . ? C2 C1 H1 118.9 . . ? C3 C2 C1 118.3(10) . . ? C3 C2 H2 120.8 . . ? C1 C2 H2 120.8 . . ? C2 C3 C4 118.9(10) . . ? C2 C3 H3 120.5 . . ? C4 C3 H3 120.5 . . ? C5 C4 C3 120.1(9) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C4 C5 N1 121.8(8) . . ? C4 C5 C6 121.6(8) . . ? N1 C5 C6 116.6(8) . . ? N2 C6 C5 110.1(7) . . ? N2 C6 H6A 109.6 . . ? C5 C6 H6A 109.6 . . ? N2 C6 H6B 109.6 . . ? C5 C6 H6B 109.6 . . ? H6A C6 H6B 108.2 . . ? O1 C7 N2 123.0(7) . . ? O1 C7 C8 118.0(7) . . ? N2 C7 C8 119.0(7) . . ? C13 C8 C9 119.2(7) . . ? C13 C8 C7 121.7(7) . . ? C9 C8 C7 119.1(7) . . ? C10 C9 C8 122.2(8) . . ? C10 C9 H9 118.9 . . ? C8 C9 H9 118.9 . . ? C9 C10 C11 119.5(8) . . ? C9 C10 H10 120.2 . . ? C11 C10 H10 120.2 . . ? C12 C11 C10 120.6(7) . . ? C12 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? C11 C12 C13 118.9(7) . . ? C11 C12 C14 120.0(7) . . ? C13 C12 C14 121.1(8) . . ? C8 C13 C12 119.5(8) . . ? C8 C13 H13 120.2 . . ? C12 C13 H13 120.2 . . ? O2 C14 N3 121.5(8) . . ? O2 C14 C12 117.4(8) . . ? N3 C14 C12 121.1(7) . . ? N3 C15 C16 110.0(6) . . ? N3 C15 H15A 109.7 . . ? C16 C15 H15A 109.7 . . ? N3 C15 H15B 109.7 . . ? C16 C15 H15B 109.7 . . ? H15A C15 H15B 108.2 . . ? N4 C16 C17 123.3(8) . . ? N4 C16 C15 116.7(8) . . ? C17 C16 C15 120.0(8) . . ? C18 C17 C16 117.7(9) . . ? C18 C17 H17 121.1 . . ? C16 C17 H17 121.1 . . ? C19 C18 C17 119.1(9) . . ? C19 C18 H18 120.5 . . ? C17 C18 H18 120.5 . . ? C18 C19 C20 119.6(9) . . ? C18 C19 H19 120.2 . . ? C20 C19 H19 120.2 . . ? N4 C20 C19 121.8(8) . . ? N4 C20 H20 119.1 . . ? C19 C20 H20 119.1 . . ? _diffrn_measured_fraction_theta_max 0.941 _diffrn_reflns_theta_full 25.27 _diffrn_measured_fraction_theta_full 0.941 _refine_diff_density_max 0.980 _refine_diff_density_min -0.550 _refine_diff_density_rms 0.122 # SQUEEZE RESULTS (APPEND TO CIF) loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons 1 0.000 0.000 0.000 291.4 40.7 2 0.000 0.500 0.500 291.4 40.8 _platon_squeeze_details ; ? ;