# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email libaolong@suda.edu.cn _publ_contact_author_name 'Baolong Li' loop_ _publ_author_name 'Xia Zhu' 'Li-Yan Wang' 'Xun-Gao Liu' 'Ju Wang' 'Baolong Li' 'Haiyan Li' data_Cu_btb_HCOO #(1) _database_code_depnum_ccdc_archive 'CCDC 810491' #TrackingRef '- Cubtb-CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H18 Cu N6 O6' _chemical_formula_sum 'C10 H18 Cu N6 O6' _chemical_formula_weight 381.84 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' 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 C2/c _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 21.091(6) _cell_length_b 8.2252(18) _cell_length_c 10.579(3) _cell_angle_alpha 90.00 _cell_angle_beta 120.686(5) _cell_angle_gamma 90.00 _cell_volume 1578.3(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3084 _cell_measurement_theta_min 3.1387 _cell_measurement_theta_max 25.3491 _exptl_crystal_description Block _exptl_crystal_colour Green _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.607 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 788 _exptl_absorpt_coefficient_mu 1.424 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.5730 _exptl_absorpt_correction_T_max 0.7447 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Rigaku Mercury CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 7373 _diffrn_reflns_av_R_equivalents 0.0258 _diffrn_reflns_av_sigmaI/netI 0.0195 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 25.34 _reflns_number_total 1448 _reflns_number_gt 1365 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2000)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2000)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0458P)^2^+1.3249P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1448 _refine_ls_number_parameters 114 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0341 _refine_ls_R_factor_gt 0.0314 _refine_ls_wR_factor_ref 0.0815 _refine_ls_wR_factor_gt 0.0791 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _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 0.29578(5) 0.7500 0.03240(17) Uani 1 2 d S . . O1 O 0.5000 0.5817(4) 0.7500 0.0611(8) Uani 1 2 d S . . O2 O 0.5000 0.0111(4) 0.7500 0.0764(11) Uani 1 2 d S . . O3 O 0.55746(10) 0.3067(2) 0.97161(19) 0.0426(4) Uani 1 1 d . . . O4 O 0.58218(12) 0.2029(3) 1.1853(2) 0.0601(6) Uani 1 1 d . . . N1 N 0.32955(11) 0.3358(3) 0.8293(2) 0.0404(5) Uani 1 1 d . . . N2 N 0.28990(12) 0.2715(4) 0.6928(3) 0.0568(7) Uani 1 1 d . . . N3 N 0.40798(10) 0.2985(2) 0.7580(2) 0.0344(4) Uani 1 1 d . . . C1 C 0.26860(14) 0.2270(3) 0.9572(3) 0.0432(6) Uani 1 1 d . . . H1A H 0.3103 0.1566 1.0168 0.052 Uiso 1 1 calc R . . H1B H 0.2341 0.1676 0.8694 0.052 Uiso 1 1 calc R . . C2 C 0.29478(15) 0.3769(3) 0.9143(3) 0.0491(6) Uani 1 1 d . . . H2A H 0.2531 0.4482 0.8565 0.059 Uiso 1 1 calc R . . H2B H 0.3298 0.4351 1.0024 0.059 Uiso 1 1 calc R . . C3 C 0.33945(14) 0.2511(4) 0.6552(3) 0.0490(6) Uani 1 1 d . . . H3A H 0.3284 0.2076 0.5651 0.059 Uiso 1 1 calc R . . C4 C 0.39870(13) 0.3520(3) 0.8657(3) 0.0394(6) Uani 1 1 d . . . H4A H 0.4358 0.3947 0.9542 0.047 Uiso 1 1 calc R . . C5 C 0.57363(17) 0.1954(3) 1.0613(3) 0.0526(7) Uani 1 1 d . . . H5A H 0.5802 0.0934 1.0316 0.063 Uiso 1 1 calc R . . H1W H 0.5286(17) 0.638(4) 0.733(4) 0.066(10) Uiso 1 1 d . . . H2W H 0.5292(19) -0.039(5) 0.740(4) 0.085(13) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0311(2) 0.0425(3) 0.0320(2) 0.000 0.02221(19) 0.000 O1 0.076(2) 0.0450(17) 0.083(2) 0.000 0.0562(19) 0.000 O2 0.120(3) 0.0476(18) 0.116(3) 0.000 0.100(3) 0.000 O3 0.0437(10) 0.0529(11) 0.0378(9) 0.0006(8) 0.0256(8) -0.0019(7) O4 0.0662(14) 0.0772(15) 0.0462(12) 0.0100(9) 0.0354(11) 0.0065(10) N1 0.0389(11) 0.0547(12) 0.0415(12) -0.0088(9) 0.0307(10) -0.0067(9) N2 0.0339(12) 0.102(2) 0.0421(13) -0.0188(12) 0.0248(10) -0.0161(12) N3 0.0324(10) 0.0425(12) 0.0353(10) -0.0070(8) 0.0224(9) -0.0063(8) C1 0.0403(13) 0.0611(16) 0.0423(14) -0.0041(12) 0.0313(12) 0.0008(11) C2 0.0538(15) 0.0599(16) 0.0574(16) -0.0102(13) 0.0456(14) -0.0040(13) C3 0.0378(14) 0.0806(18) 0.0362(14) -0.0170(13) 0.0242(12) -0.0147(13) C4 0.0377(13) 0.0503(14) 0.0402(13) -0.0128(11) 0.0271(11) -0.0110(11) C5 0.0663(19) 0.0591(18) 0.0467(16) 0.0043(13) 0.0393(15) 0.0085(13) _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 N3 1.9854(19) . ? Cu1 N3 1.9854(19) 2_656 ? Cu1 O3 2.0182(18) . ? Cu1 O3 2.0182(18) 2_656 ? Cu1 O2 2.341(3) . ? Cu1 O1 2.352(3) . ? O1 H1W 0.85(3) . ? O2 H2W 0.79(3) . ? O3 C5 1.235(3) . ? O4 C5 1.231(3) . ? N1 C4 1.312(3) . ? N1 N2 1.354(3) . ? N1 C2 1.460(3) . ? N2 C3 1.305(3) . ? N3 C4 1.326(3) . ? N3 C3 1.349(3) . ? C1 C2 1.512(4) . ? C1 C1 1.518(4) 7_557 ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 H3A 0.9300 . ? C4 H4A 0.9300 . ? C5 H5A 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 N3 Cu1 N3 178.70(11) . 2_656 ? N3 Cu1 O3 88.31(8) . . ? N3 Cu1 O3 91.63(8) 2_656 . ? N3 Cu1 O3 91.63(8) . 2_656 ? N3 Cu1 O3 88.31(8) 2_656 2_656 ? O3 Cu1 O3 174.88(10) . 2_656 ? N3 Cu1 O2 90.65(5) . . ? N3 Cu1 O2 90.65(5) 2_656 . ? O3 Cu1 O2 92.56(5) . . ? O3 Cu1 O2 92.56(5) 2_656 . ? N3 Cu1 O1 89.35(5) . . ? N3 Cu1 O1 89.35(5) 2_656 . ? O3 Cu1 O1 87.44(5) . . ? O3 Cu1 O1 87.44(5) 2_656 . ? O2 Cu1 O1 180.000(1) . . ? Cu1 O1 H1W 123(2) . . ? Cu1 O2 H2W 122(3) . . ? C5 O3 Cu1 128.77(18) . . ? C4 N1 N2 109.95(19) . . ? C4 N1 C2 129.0(2) . . ? N2 N1 C2 121.1(2) . . ? C3 N2 N1 102.8(2) . . ? C4 N3 C3 102.8(2) . . ? C4 N3 Cu1 128.07(16) . . ? C3 N3 Cu1 129.12(17) . . ? C2 C1 C1 110.8(3) . 7_557 ? C2 C1 H1A 109.5 . . ? C1 C1 H1A 109.5 7_557 . ? C2 C1 H1B 109.5 . . ? C1 C1 H1B 109.5 7_557 . ? H1A C1 H1B 108.1 . . ? N1 C2 C1 111.8(2) . . ? N1 C2 H2A 109.3 . . ? C1 C2 H2A 109.3 . . ? N1 C2 H2B 109.3 . . ? C1 C2 H2B 109.3 . . ? H2A C2 H2B 107.9 . . ? N2 C3 N3 114.4(2) . . ? N2 C3 H3A 122.8 . . ? N3 C3 H3A 122.8 . . ? N1 C4 N3 110.1(2) . . ? N1 C4 H4A 124.9 . . ? N3 C4 H4A 124.9 . . ? O4 C5 O3 127.9(3) . . ? O4 C5 H5A 116.1 . . ? O3 C5 H5A 116.1 . . ? 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 N3 Cu1 O3 C5 81.7(2) . . . . ? N3 Cu1 O3 C5 -99.7(2) 2_656 . . . ? O2 Cu1 O3 C5 -8.9(2) . . . . ? O1 Cu1 O3 C5 171.1(2) . . . . ? C4 N1 N2 C3 0.6(3) . . . . ? C2 N1 N2 C3 -179.5(3) . . . . ? O3 Cu1 N3 C4 21.8(2) . . . . ? O3 Cu1 N3 C4 -153.1(2) 2_656 . . . ? O2 Cu1 N3 C4 114.3(2) . . . . ? O1 Cu1 N3 C4 -65.7(2) . . . . ? O3 Cu1 N3 C3 -160.1(2) . . . . ? O3 Cu1 N3 C3 25.0(2) 2_656 . . . ? O2 Cu1 N3 C3 -67.6(2) . . . . ? O1 Cu1 N3 C3 112.4(2) . . . . ? C4 N1 C2 C1 -113.1(3) . . . . ? N2 N1 C2 C1 67.0(3) . . . . ? C1 C1 C2 N1 -178.9(3) 7_557 . . . ? N1 N2 C3 N3 -0.2(4) . . . . ? C4 N3 C3 N2 -0.2(3) . . . . ? Cu1 N3 C3 N2 -178.6(2) . . . . ? N2 N1 C4 N3 -0.7(3) . . . . ? C2 N1 C4 N3 179.3(2) . . . . ? C3 N3 C4 N1 0.5(3) . . . . ? Cu1 N3 C4 N1 179.01(16) . . . . ? Cu1 O3 C5 O4 -149.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.34 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.337 _refine_diff_density_min -0.351 _refine_diff_density_rms 0.052 ###======The End of CIF data_Cu_btb_Cl #(2) _database_code_depnum_ccdc_archive 'CCDC 810492' #TrackingRef '- Cubtb-CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H24 Cl2 Cu N12' _chemical_formula_sum 'C16 H24 Cl2 Cu N12' _chemical_formula_weight 518.91 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' 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' 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 7.4564(13) _cell_length_b 17.654(3) _cell_length_c 8.7158(16) _cell_angle_alpha 90.00 _cell_angle_beta 114.808(3) _cell_angle_gamma 90.00 _cell_volume 1041.4(3) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 3837 _cell_measurement_theta_min 3.0312 _cell_measurement_theta_max 25.3491 _exptl_crystal_description Block _exptl_crystal_colour Blue _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.39 _exptl_crystal_size_min 0.31 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.655 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 534 _exptl_absorpt_coefficient_mu 1.339 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.5542 _exptl_absorpt_correction_T_max 0.6817 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Mercury CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 9977 _diffrn_reflns_av_R_equivalents 0.0290 _diffrn_reflns_av_sigmaI/netI 0.0240 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.22 _diffrn_reflns_theta_max 25.35 _reflns_number_total 1894 _reflns_number_gt 1807 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2000)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2000)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0414P)^2^+0.5931P] 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 1894 _refine_ls_number_parameters 142 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0331 _refine_ls_R_factor_gt 0.0305 _refine_ls_wR_factor_ref 0.0799 _refine_ls_wR_factor_gt 0.0784 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.076 _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 0.5000 0.0000 0.02525(14) Uani 1 2 d S . . Cl1 Cl 0.89989(8) 0.53462(3) 0.18901(7) 0.03305(17) Uani 1 1 d . . . N1 N 0.3760(3) 0.40441(10) 0.3801(2) 0.0251(4) Uani 1 1 d . . . N2 N 0.5737(3) 0.41159(11) 0.4737(2) 0.0306(4) Uani 1 1 d . . . N3 N 0.4874(3) 0.45367(10) 0.2092(2) 0.0246(4) Uani 1 1 d . . . N4 N -0.3044(3) 0.18930(11) 0.3380(2) 0.0293(4) Uani 1 1 d . . . N5 N -0.4647(3) 0.22228(11) 0.3485(2) 0.0338(5) Uani 1 1 d . . . N6 N -0.4333(2) 0.10114(10) 0.4324(2) 0.0237(4) Uani 1 1 d . . . C1 C 0.2516(4) 0.37016(15) 0.4535(3) 0.0354(6) Uani 1 1 d . . . H1A H 0.1968 0.4101 0.4992 0.043 Uiso 1 1 calc R . . H1B H 0.3325 0.3369 0.5471 0.043 Uiso 1 1 calc R . . C2 C 0.0858(3) 0.32517(12) 0.3255(3) 0.0260(5) Uani 1 1 d . . . H2A H 0.1395 0.2905 0.2675 0.031 Uiso 1 1 calc R . . H2B H -0.0057 0.3597 0.2408 0.031 Uiso 1 1 calc R . . C3 C -0.0270(3) 0.27968(12) 0.4041(3) 0.0268(5) Uani 1 1 d . . . H3A H 0.0653 0.2478 0.4950 0.032 Uiso 1 1 calc R . . H3B H -0.0915 0.3143 0.4533 0.032 Uiso 1 1 calc R . . C4 C -0.1804(4) 0.23051(16) 0.2732(3) 0.0421(6) Uani 1 1 d . . . H4A H -0.2650 0.2624 0.1783 0.051 Uiso 1 1 calc R . . H4B H -0.1138 0.1939 0.2301 0.051 Uiso 1 1 calc R . . C5 C 0.6343(3) 0.44185(12) 0.3659(3) 0.0284(5) Uani 1 1 d . . . H5A H 0.7671 0.4542 0.3945 0.034 Uiso 1 1 calc R . . C6 C 0.3274(3) 0.42973(13) 0.2248(3) 0.0267(5) Uani 1 1 d . . . H6A H 0.1986 0.4306 0.1383 0.032 Uiso 1 1 calc R . . C7 C -0.5364(3) 0.16680(12) 0.4055(3) 0.0286(5) Uani 1 1 d . . . H7A H -0.6498 0.1721 0.4261 0.034 Uiso 1 1 calc R . . C8 C -0.2885(3) 0.11779(13) 0.3861(3) 0.0267(5) Uani 1 1 d . . . H8A H -0.1906 0.0839 0.3875 0.032 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 0.0354(2) 0.0196(2) 0.0331(2) 0.00321(14) 0.02646(19) 0.00248(14) Cl1 0.0215(3) 0.0460(4) 0.0340(3) 0.0043(3) 0.0140(2) 0.0000(2) N1 0.0257(9) 0.0292(10) 0.0234(9) -0.0016(7) 0.0133(8) -0.0073(7) N2 0.0261(10) 0.0314(10) 0.0318(10) 0.0006(8) 0.0099(8) -0.0068(8) N3 0.0259(9) 0.0238(9) 0.0311(10) 0.0006(8) 0.0188(8) -0.0007(7) N4 0.0301(10) 0.0358(11) 0.0241(9) -0.0038(8) 0.0133(8) -0.0130(8) N5 0.0370(11) 0.0274(10) 0.0378(11) -0.0017(8) 0.0164(9) -0.0049(8) N6 0.0227(9) 0.0247(9) 0.0275(9) -0.0021(7) 0.0143(8) -0.0033(7) C1 0.0402(13) 0.0447(14) 0.0302(12) -0.0041(11) 0.0234(11) -0.0186(11) C2 0.0275(11) 0.0278(11) 0.0243(11) 0.0029(9) 0.0125(9) -0.0046(9) C3 0.0287(11) 0.0279(11) 0.0275(11) 0.0020(9) 0.0152(10) -0.0041(9) C4 0.0471(15) 0.0550(16) 0.0292(12) -0.0034(11) 0.0209(11) -0.0281(12) C5 0.0245(11) 0.0275(11) 0.0358(12) 0.0003(10) 0.0152(10) -0.0016(9) C6 0.0244(11) 0.0340(12) 0.0246(11) 0.0012(9) 0.0130(9) -0.0047(9) C7 0.0257(11) 0.0268(11) 0.0374(12) -0.0033(10) 0.0171(10) -0.0027(9) C8 0.0235(11) 0.0330(12) 0.0259(11) -0.0018(9) 0.0126(9) -0.0039(9) _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 N6 2.0069(17) 4_665 ? Cu1 N6 2.0069(17) 2 ? Cu1 N3 2.0359(17) . ? Cu1 N3 2.0359(17) 3_665 ? Cu1 Cl1 2.8029(7) 3_665 ? Cu1 Cl1 2.8029(7) . ? N1 C6 1.324(3) . ? N1 N2 1.359(3) . ? N1 C1 1.460(3) . ? N2 C5 1.315(3) . ? N3 C6 1.325(3) . ? N3 C5 1.362(3) . ? N4 C8 1.320(3) . ? N4 N5 1.367(3) . ? N4 C4 1.463(3) . ? N5 C7 1.309(3) . ? N6 C8 1.335(3) . ? N6 C7 1.356(3) . ? N6 Cu1 2.0069(17) 2_545 ? C1 C2 1.499(3) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C2 C3 1.518(3) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C3 C4 1.506(3) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C5 H5A 0.9400 . ? C6 H6A 0.9400 . ? C7 H7A 0.9400 . ? C8 H8A 0.9400 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N6 Cu1 N6 180.0 4_665 2 ? N6 Cu1 N3 90.89(7) 4_665 . ? N6 Cu1 N3 89.11(7) 2 . ? N6 Cu1 N3 89.11(7) 4_665 3_665 ? N6 Cu1 N3 90.89(7) 2 3_665 ? N3 Cu1 N3 180.00(10) . 3_665 ? N6 Cu1 Cl1 88.11(5) 4_665 3_665 ? N6 Cu1 Cl1 91.89(5) 2 3_665 ? N3 Cu1 Cl1 90.07(5) . 3_665 ? N3 Cu1 Cl1 89.93(5) 3_665 3_665 ? N6 Cu1 Cl1 91.89(5) 4_665 . ? N6 Cu1 Cl1 88.11(5) 2 . ? N3 Cu1 Cl1 89.93(5) . . ? N3 Cu1 Cl1 90.07(5) 3_665 . ? Cl1 Cu1 Cl1 180.0 3_665 . ? C6 N1 N2 110.16(17) . . ? C6 N1 C1 129.51(19) . . ? N2 N1 C1 120.30(18) . . ? C5 N2 N1 102.73(17) . . ? C6 N3 C5 103.17(17) . . ? C6 N3 Cu1 127.00(15) . . ? C5 N3 Cu1 129.80(14) . . ? C8 N4 N5 110.50(17) . . ? C8 N4 C4 127.7(2) . . ? N5 N4 C4 121.7(2) . . ? C7 N5 N4 102.39(18) . . ? C8 N6 C7 103.35(18) . . ? C8 N6 Cu1 128.05(15) . 2_545 ? C7 N6 Cu1 128.27(14) . 2_545 ? N1 C1 C2 111.77(18) . . ? N1 C1 H1A 109.3 . . ? C2 C1 H1A 109.3 . . ? N1 C1 H1B 109.3 . . ? C2 C1 H1B 109.3 . . ? H1A C1 H1B 107.9 . . ? C1 C2 C3 112.62(17) . . ? C1 C2 H2A 109.1 . . ? C3 C2 H2A 109.1 . . ? C1 C2 H2B 109.1 . . ? C3 C2 H2B 109.1 . . ? H2A C2 H2B 107.8 . . ? C4 C3 C2 110.57(17) . . ? C4 C3 H3A 109.5 . . ? C2 C3 H3A 109.5 . . ? C4 C3 H3B 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 108.1 . . ? N4 C4 C3 113.33(19) . . ? N4 C4 H4A 108.9 . . ? C3 C4 H4A 108.9 . . ? N4 C4 H4B 108.9 . . ? C3 C4 H4B 108.9 . . ? H4A C4 H4B 107.7 . . ? N2 C5 N3 113.99(19) . . ? N2 C5 H5A 123.0 . . ? N3 C5 H5A 123.0 . . ? N1 C6 N3 109.94(19) . . ? N1 C6 H6A 125.0 . . ? N3 C6 H6A 125.0 . . ? N5 C7 N6 114.42(19) . . ? N5 C7 H7A 122.8 . . ? N6 C7 H7A 122.8 . . ? N4 C8 N6 109.33(19) . . ? N4 C8 H8A 125.3 . . ? N6 C8 H8A 125.3 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 N1 N2 C5 0.1(2) . . . . ? C1 N1 N2 C5 178.13(19) . . . . ? N6 Cu1 N3 C6 -95.86(18) 4_665 . . . ? N6 Cu1 N3 C6 84.14(18) 2 . . . ? Cl1 Cu1 N3 C6 -7.75(18) 3_665 . . . ? Cl1 Cu1 N3 C6 172.25(18) . . . . ? N6 Cu1 N3 C5 86.58(19) 4_665 . . . ? N6 Cu1 N3 C5 -93.42(19) 2 . . . ? Cl1 Cu1 N3 C5 174.69(18) 3_665 . . . ? Cl1 Cu1 N3 C5 -5.31(18) . . . . ? C8 N4 N5 C7 0.5(2) . . . . ? C4 N4 N5 C7 177.85(19) . . . . ? C6 N1 C1 C2 32.5(3) . . . . ? N2 N1 C1 C2 -145.1(2) . . . . ? N1 C1 C2 C3 171.51(19) . . . . ? C1 C2 C3 C4 -175.2(2) . . . . ? C8 N4 C4 C3 -100.3(3) . . . . ? N5 N4 C4 C3 82.9(3) . . . . ? C2 C3 C4 N4 -175.8(2) . . . . ? N1 N2 C5 N3 -0.6(2) . . . . ? C6 N3 C5 N2 0.8(2) . . . . ? Cu1 N3 C5 N2 178.83(14) . . . . ? N2 N1 C6 N3 0.4(3) . . . . ? C1 N1 C6 N3 -177.4(2) . . . . ? C5 N3 C6 N1 -0.7(2) . . . . ? Cu1 N3 C6 N1 -178.79(14) . . . . ? N4 N5 C7 N6 0.2(2) . . . . ? C8 N6 C7 N5 -0.8(3) . . . . ? Cu1 N6 C7 N5 -174.47(15) 2_545 . . . ? N5 N4 C8 N6 -1.1(2) . . . . ? C4 N4 C8 N6 -178.17(19) . . . . ? C7 N6 C8 N4 1.1(2) . . . . ? Cu1 N6 C8 N4 174.79(13) 2_545 . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.347 _refine_diff_density_min -0.324 _refine_diff_density_rms 0.053 ###======The End of CIF data_Cu_btb_NCS #(3) _database_code_depnum_ccdc_archive 'CCDC 810493' #TrackingRef '- Cubtb-CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H12 Cu N8 S2' _chemical_formula_sum 'C10 H12 Cu N8 S2' _chemical_formula_weight 371.94 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' 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 9.565(2) _cell_length_b 8.5582(19) _cell_length_c 9.4197(17) _cell_angle_alpha 90.00 _cell_angle_beta 106.288(5) _cell_angle_gamma 90.00 _cell_volume 740.2(3) _cell_formula_units_Z 2 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 3552 _cell_measurement_theta_min 3.2542 _cell_measurement_theta_max 27.4835 _exptl_crystal_description block _exptl_crystal_colour Green _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.669 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 378 _exptl_absorpt_coefficient_mu 1.763 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.763 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(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 'Rigaku Mercury CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 7955 _diffrn_reflns_av_R_equivalents 0.0415 _diffrn_reflns_av_sigmaI/netI 0.0232 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.25 _diffrn_reflns_theta_max 27.45 _reflns_number_total 1698 _reflns_number_gt 1615 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2000)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2000)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0461P)^2^+0.2222P] 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 1698 _refine_ls_number_parameters 97 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0285 _refine_ls_R_factor_gt 0.0270 _refine_ls_wR_factor_ref 0.0760 _refine_ls_wR_factor_gt 0.0748 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _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 1.0000 0.0000 1.0000 0.02085(12) Uani 1 2 d S . . S1 S 1.15068(5) 0.19835(6) 0.60557(6) 0.03818(15) Uani 1 1 d . . . N1 N 0.63042(14) 0.27354(14) 0.89588(14) 0.0198(3) Uani 1 1 d . . . N2 N 0.57633(14) 0.15288(15) 0.95923(15) 0.0233(3) Uani 1 1 d . . . N3 N 0.80991(13) 0.11067(15) 0.96881(15) 0.0207(3) Uani 1 1 d . . . N4 N 1.01688(16) 0.07672(18) 0.80875(16) 0.0289(3) Uani 1 1 d . . . C1 C 0.68871(17) 0.05862(18) 1.00187(18) 0.0217(3) Uani 1 1 d . . . H1A H 0.6855 -0.0354 1.0504 0.026 Uiso 1 1 calc R . . C2 C 0.76915(17) 0.24636(18) 0.90234(18) 0.0221(3) Uani 1 1 d . . . H2A H 0.8282 0.3123 0.8659 0.027 Uiso 1 1 calc R . . C3 C 0.53523(18) 0.40255(19) 0.82639(18) 0.0244(3) Uani 1 1 d . . . H3A H 0.4672 0.3659 0.7356 0.029 Uiso 1 1 calc R . . H3B H 0.5936 0.4849 0.8010 0.029 Uiso 1 1 calc R . . C4 C 0.45073(18) 0.4684(2) 0.92740(19) 0.0244(3) Uani 1 1 d . . . H4A H 0.3892 0.3870 0.9490 0.029 Uiso 1 1 calc R . . H4B H 0.3879 0.5518 0.8762 0.029 Uiso 1 1 calc R . . C5 C 1.07197(16) 0.12981(19) 0.72473(17) 0.0226(3) 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 0.01878(17) 0.02435(18) 0.02201(18) 0.00541(9) 0.00999(12) 0.00582(9) S1 0.0373(3) 0.0391(3) 0.0473(3) 0.0200(2) 0.0270(2) 0.01303(19) N1 0.0205(6) 0.0160(6) 0.0244(7) 0.0007(5) 0.0088(5) 0.0012(5) N2 0.0207(6) 0.0199(6) 0.0309(7) 0.0033(5) 0.0100(5) -0.0006(5) N3 0.0186(6) 0.0188(6) 0.0261(7) 0.0010(5) 0.0085(5) 0.0007(5) N4 0.0304(7) 0.0337(8) 0.0253(7) 0.0062(6) 0.0124(6) 0.0067(6) C1 0.0205(7) 0.0171(7) 0.0288(8) 0.0014(6) 0.0088(6) -0.0009(6) C2 0.0207(7) 0.0191(7) 0.0287(8) 0.0023(6) 0.0105(6) 0.0004(5) C3 0.0259(8) 0.0230(8) 0.0242(8) 0.0042(6) 0.0066(6) 0.0066(6) C4 0.0207(8) 0.0232(7) 0.0287(9) 0.0010(7) 0.0062(7) 0.0061(6) C5 0.0215(7) 0.0224(7) 0.0235(7) 0.0020(6) 0.0055(6) 0.0061(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N4 1.9661(14) . ? Cu1 N4 1.9661(14) 3_757 ? Cu1 N3 1.9975(13) . ? Cu1 N3 1.9975(13) 3_757 ? Cu1 S1 2.9878(7) 4_566 ? Cu1 S1 2.9878(7) 2_746 ? S1 C5 1.6263(17) . ? N1 C2 1.332(2) . ? N1 N2 1.3651(18) . ? N1 C3 1.4636(19) . ? N2 C1 1.314(2) . ? N3 C2 1.325(2) . ? N3 C1 1.3571(19) . ? N4 C5 1.159(2) . ? C1 H1A 0.9300 . ? C2 H2A 0.9300 . ? C3 C4 1.519(2) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C4 1.526(3) 3_667 ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N4 Cu1 N4 180.0 . 3_757 ? N4 Cu1 N3 90.70(6) . . ? N4 Cu1 N3 89.30(6) 3_757 . ? N4 Cu1 N3 89.30(6) . 3_757 ? N4 Cu1 N3 90.70(6) 3_757 3_757 ? N3 Cu1 N3 180.0 . 3_757 ? N4 Cu1 S1 81.98(5) . 4_566 ? N4 Cu1 S1 98.02(5) 3_757 4_566 ? N3 Cu1 S1 88.48(4) . 4_566 ? N3 Cu1 S1 91.52(4) 3_757 4_566 ? N4 Cu1 S1 98.02(5) . 2_746 ? N4 Cu1 S1 81.98(5) 3_757 2_746 ? N3 Cu1 S1 91.52(4) . 2_746 ? N3 Cu1 S1 88.48(4) 3_757 2_746 ? S1 Cu1 S1 180.0 4_566 2_746 ? C2 N1 N2 110.05(13) . . ? C2 N1 C3 129.73(13) . . ? N2 N1 C3 120.11(13) . . ? C1 N2 N1 102.72(12) . . ? C2 N3 C1 103.83(13) . . ? C2 N3 Cu1 128.32(11) . . ? C1 N3 Cu1 127.70(11) . . ? C5 N4 Cu1 157.84(14) . . ? N2 C1 N3 114.00(14) . . ? N2 C1 H1A 123.0 . . ? N3 C1 H1A 123.0 . . ? N3 C2 N1 109.39(14) . . ? N3 C2 H2A 125.3 . . ? N1 C2 H2A 125.3 . . ? N1 C3 C4 111.92(13) . . ? N1 C3 H3A 109.2 . . ? C4 C3 H3A 109.2 . . ? N1 C3 H3B 109.2 . . ? C4 C3 H3B 109.2 . . ? H3A C3 H3B 107.9 . . ? C3 C4 C4 112.92(17) . 3_667 ? C3 C4 H4A 109.0 . . ? C4 C4 H4A 109.0 3_667 . ? C3 C4 H4B 109.0 . . ? C4 C4 H4B 109.0 3_667 . ? H4A C4 H4B 107.8 . . ? N4 C5 S1 178.07(15) . . ? 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 C2 N1 N2 C1 0.41(17) . . . . ? C3 N1 N2 C1 176.95(13) . . . . ? N4 Cu1 N3 C2 -34.77(14) . . . . ? N4 Cu1 N3 C2 145.23(14) 3_757 . . . ? S1 Cu1 N3 C2 47.18(14) 4_566 . . . ? S1 Cu1 N3 C2 -132.82(14) 2_746 . . . ? N4 Cu1 N3 C1 140.14(14) . . . . ? N4 Cu1 N3 C1 -39.86(14) 3_757 . . . ? S1 Cu1 N3 C1 -137.90(13) 4_566 . . . ? S1 Cu1 N3 C1 42.10(13) 2_746 . . . ? N3 Cu1 N4 C5 136.1(4) . . . . ? N3 Cu1 N4 C5 -43.9(4) 3_757 . . . ? S1 Cu1 N4 C5 47.7(4) 4_566 . . . ? S1 Cu1 N4 C5 -132.3(4) 2_746 . . . ? N1 N2 C1 N3 -0.51(18) . . . . ? C2 N3 C1 N2 0.41(18) . . . . ? Cu1 N3 C1 N2 -175.48(11) . . . . ? C1 N3 C2 N1 -0.13(18) . . . . ? Cu1 N3 C2 N1 175.74(10) . . . . ? N2 N1 C2 N3 -0.18(19) . . . . ? C3 N1 C2 N3 -176.29(14) . . . . ? C2 N1 C3 C4 -134.04(17) . . . . ? N2 N1 C3 C4 50.18(19) . . . . ? N1 C3 C4 C4 59.8(2) . . . 3_667 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.382 _refine_diff_density_min -0.533 _refine_diff_density_rms 0.066 ###======The End of CIF data_Cu_btb_ClO4 #(4) _database_code_depnum_ccdc_archive 'CCDC 810494' #TrackingRef '- Cubtb-CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H28 Cu N12 O2, 2(Cl O4' _chemical_formula_sum 'C16 H28 Cl2 Cu N12 O10' _chemical_formula_weight 682.94 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' 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Fddd _symmetry_space_group_name_Hall '-F 2uv 2vw ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/4, z+1/4' 'x+1/4, -y, z+1/4' '-x+1/4, -y+3/4, z+1/2' 'x, y+1/2, z+1/2' '-x, y+3/4, z+3/4' 'x+1/4, -y+1/2, z+3/4' '-x+1/4, -y+5/4, z+1' 'x+1/2, y, z+1/2' '-x+1/2, y+1/4, z+3/4' 'x+3/4, -y, z+3/4' '-x+3/4, -y+3/4, z+1' 'x+1/2, y+1/2, z' '-x+1/2, y+3/4, z+1/4' 'x+3/4, -y+1/2, z+1/4' '-x+3/4, -y+5/4, z+1/2' '-x, -y, -z' 'x, -y-1/4, -z-1/4' '-x-1/4, y, -z-1/4' 'x-1/4, y-3/4, -z-1/2' '-x, -y+1/2, -z+1/2' 'x, -y+1/4, -z+1/4' '-x-1/4, y+1/2, -z+1/4' 'x-1/4, y-1/4, -z' '-x+1/2, -y, -z+1/2' 'x+1/2, -y-1/4, -z+1/4' '-x+1/4, y, -z+1/4' 'x+1/4, y-3/4, -z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/4, -z-1/4' '-x+1/4, y+1/2, -z-1/4' 'x+1/4, y-1/4, -z-1/2' _cell_length_a 13.143(2) _cell_length_b 17.513(3) _cell_length_c 25.348(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5834.2(16) _cell_formula_units_Z 8 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 4526 _cell_measurement_theta_min 3.0910 _cell_measurement_theta_max 25.3491 _exptl_crystal_description Block _exptl_crystal_colour blue _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.555 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2808 _exptl_absorpt_coefficient_mu 1.001 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.5945 _exptl_absorpt_correction_T_max 0.8250 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _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 'Rigaku Mercury CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 13310 _diffrn_reflns_av_R_equivalents 0.0320 _diffrn_reflns_av_sigmaI/netI 0.0155 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 25.34 _reflns_number_total 1343 _reflns_number_gt 1300 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2000)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2000)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0892P)^2^+32.6100P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1343 _refine_ls_number_parameters 113 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0554 _refine_ls_R_factor_gt 0.0539 _refine_ls_wR_factor_ref 0.1555 _refine_ls_wR_factor_gt 0.1541 _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_restrained_S_all 1.100 _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 0.6250 0.1250 0.1250 0.0290(3) Uani 1 4 d S . . O1 O 0.6250 -0.0127(2) 0.1250 0.0459(10) Uani 1 2 d SD . . N1 N 0.8308(2) 0.16668(18) 0.24523(11) 0.0408(7) Uani 1 1 d . . . N2 N 0.8686(3) 0.0989(2) 0.2303(2) 0.0652(12) Uani 1 1 d . . . N3 N 0.7331(2) 0.12908(15) 0.18110(11) 0.0349(7) Uani 1 1 d . . . C1 C 0.9567(3) 0.2680(3) 0.26480(18) 0.0558(11) Uani 1 1 d . . . H1A H 0.9217 0.3037 0.2412 0.067 Uiso 1 1 calc R . . H1B H 0.9848 0.2978 0.2941 0.067 Uiso 1 1 calc R . . C2 C 0.8790(3) 0.2122(3) 0.28675(16) 0.0531(11) Uani 1 1 d . . . H2A H 0.9126 0.1779 0.3119 0.064 Uiso 1 1 calc R . . H2B H 0.8264 0.2407 0.3059 0.064 Uiso 1 1 calc R . . C3 C 0.8081(3) 0.0790(2) 0.1913(2) 0.0606(12) Uani 1 1 d . . . H3A H 0.8167 0.0335 0.1721 0.073 Uiso 1 1 calc R . . C4 C 0.7503(2) 0.1839(2) 0.21615(13) 0.0360(8) Uani 1 1 d . . . H4A H 0.7111 0.2284 0.2198 0.043 Uiso 1 1 calc R . . H1W H 0.567(3) -0.041(3) 0.1305(19) 0.072(15) Uiso 1 1 d D . . Cl1 Cl 0.3750 -0.1250 0.11810(5) 0.0474(4) Uani 1 2 d S . . O2 O 0.4347(6) -0.0782(4) 0.1501(2) 0.087(2) Uani 0.67 1 d P . . O3 O 0.3750 -0.1250 0.0669(3) 0.254(7) Uani 1.33 2 d SP . . O4 O 0.3197(9) -0.0477(5) 0.1248(4) 0.072(3) Uani 0.33 1 d P . . O5 O 0.2796(9) -0.1227(15) 0.1240(9) 0.141(8) Uani 0.33 1 d P . . 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 0.0184(4) 0.0340(5) 0.0347(5) 0.000 0.000 0.000 O1 0.0294(19) 0.0314(19) 0.077(3) 0.000 0.0043(17) 0.000 N1 0.0350(17) 0.0445(17) 0.0427(17) 0.0033(13) -0.0085(13) -0.0085(14) N2 0.052(2) 0.045(2) 0.098(3) -0.003(2) -0.040(2) 0.0062(16) N3 0.0255(14) 0.0364(15) 0.0427(16) -0.0023(12) -0.0059(12) 0.0002(10) C1 0.049(2) 0.062(3) 0.056(2) -0.013(2) -0.0108(19) -0.015(2) C2 0.049(2) 0.070(3) 0.040(2) -0.0023(19) -0.0080(17) -0.0188(19) C3 0.051(2) 0.040(2) 0.090(3) -0.018(2) -0.032(2) 0.0118(18) C4 0.0295(17) 0.0412(18) 0.0374(17) 0.0037(14) -0.0009(14) -0.0018(14) Cl1 0.0409(8) 0.0564(9) 0.0450(7) 0.000 0.000 -0.0189(6) O2 0.092(5) 0.101(5) 0.067(3) -0.013(3) 0.000(3) -0.065(4) O3 0.47(2) 0.208(10) 0.087(5) 0.000 0.000 0.032(10) O4 0.084(8) 0.044(5) 0.089(7) 0.011(5) 0.050(6) 0.017(5) O5 0.013(6) 0.24(2) 0.173(18) -0.079(15) 0.012(7) -0.014(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N3 2.012(3) . ? Cu1 N3 2.012(3) 8_644 ? Cu1 N3 2.012(3) 27_655 ? Cu1 N3 2.012(3) 22 ? Cu1 O1 2.412(4) . ? Cu1 O1 2.412(4) 22 ? O1 H1W 0.919(19) . ? N1 C4 1.324(4) . ? N1 N2 1.341(5) . ? N1 C2 1.464(5) . ? N2 C3 1.316(6) . ? N3 C4 1.327(4) . ? N3 C3 1.344(5) . ? C1 C1 1.501(9) 21_755 ? C1 C2 1.520(6) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C3 H3A 0.9400 . ? C4 H4A 0.9400 . ? Cl1 O5 1.264(11) 12_544 ? Cl1 O5 1.264(11) . ? Cl1 O3 1.297(7) . ? Cl1 O2 1.396(5) . ? Cl1 O2 1.396(5) 12_544 ? Cl1 O4 1.545(9) 12_544 ? Cl1 O4 1.545(9) . ? 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 N3 Cu1 N3 90.03(17) . 8_644 ? N3 Cu1 N3 175.93(15) . 27_655 ? N3 Cu1 N3 90.12(17) 8_644 27_655 ? N3 Cu1 N3 90.12(17) . 22 ? N3 Cu1 N3 175.93(15) 8_644 22 ? N3 Cu1 N3 90.03(17) 27_655 22 ? N3 Cu1 O1 92.04(7) . . ? N3 Cu1 O1 87.96(7) 8_644 . ? N3 Cu1 O1 92.04(7) 27_655 . ? N3 Cu1 O1 87.96(7) 22 . ? N3 Cu1 O1 87.96(7) . 22 ? N3 Cu1 O1 92.04(7) 8_644 22 ? N3 Cu1 O1 87.96(7) 27_655 22 ? N3 Cu1 O1 92.04(7) 22 22 ? O1 Cu1 O1 180.0 . 22 ? Cu1 O1 H1W 123(3) . . ? C4 N1 N2 109.9(3) . . ? C4 N1 C2 128.4(4) . . ? N2 N1 C2 121.6(3) . . ? C3 N2 N1 102.9(3) . . ? C4 N3 C3 102.6(3) . . ? C4 N3 Cu1 128.3(2) . . ? C3 N3 Cu1 129.1(3) . . ? C1 C1 C2 115.0(5) 21_755 . ? C1 C1 H1A 108.5 21_755 . ? C2 C1 H1A 108.5 . . ? C1 C1 H1B 108.5 21_755 . ? C2 C1 H1B 108.5 . . ? H1A C1 H1B 107.5 . . ? N1 C2 C1 112.2(3) . . ? N1 C2 H2A 109.2 . . ? C1 C2 H2A 109.2 . . ? N1 C2 H2B 109.2 . . ? C1 C2 H2B 109.2 . . ? H2A C2 H2B 107.9 . . ? N2 C3 N3 114.5(4) . . ? N2 C3 H3A 122.8 . . ? N3 C3 H3A 122.8 . . ? N1 C4 N3 110.1(3) . . ? N1 C4 H4A 124.9 . . ? N3 C4 H4A 124.9 . . ? O5 Cl1 O5 166(2) 12_544 . ? O5 Cl1 O3 96.8(10) 12_544 . ? O5 Cl1 O3 96.8(10) . . ? O5 Cl1 O2 52.5(12) 12_544 . ? O5 Cl1 O2 118.1(9) . . ? O3 Cl1 O2 125.6(3) . . ? O5 Cl1 O2 118.1(9) 12_544 12_544 ? O5 Cl1 O2 52.5(12) . 12_544 ? O3 Cl1 O2 125.6(3) . 12_544 ? O2 Cl1 O2 108.8(5) . 12_544 ? O5 Cl1 O4 59.5(11) 12_544 12_544 ? O5 Cl1 O4 118.8(12) . 12_544 ? O3 Cl1 O4 96.3(4) . 12_544 ? O2 Cl1 O4 100.7(5) . 12_544 ? O2 Cl1 O4 71.7(6) 12_544 12_544 ? O5 Cl1 O4 118.8(12) 12_544 . ? O5 Cl1 O4 59.5(11) . . ? O3 Cl1 O4 96.3(4) . . ? O2 Cl1 O4 71.7(6) . . ? O2 Cl1 O4 100.7(5) 12_544 . ? O4 Cl1 O4 167.5(8) 12_544 . ? O5 O2 Cl1 58.0(7) 12_544 . ? O5 O2 O4 111.3(9) 12_544 . ? Cl1 O2 O4 58.2(5) . . ? O5 O4 Cl1 50.3(6) . . ? O5 O4 O2 92.5(9) . . ? Cl1 O4 O2 50.1(4) . . ? O2 O5 Cl1 69.5(9) 12_544 . ? Cl1 O5 O4 70.2(9) . . ? 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 C4 N1 N2 C3 1.1(5) . . . . ? C2 N1 N2 C3 -176.9(4) . . . . ? N3 Cu1 N3 C4 -65.4(3) 8_644 . . . ? N3 Cu1 N3 C4 26.7(3) 27_655 . . . ? N3 Cu1 N3 C4 118.7(3) 22 . . . ? O1 Cu1 N3 C4 -153.3(3) . . . . ? O1 Cu1 N3 C4 26.7(3) 22 . . . ? N3 Cu1 N3 C3 117.5(4) 8_644 . . . ? N3 Cu1 N3 C3 -150.4(4) 27_655 . . . ? N3 Cu1 N3 C3 -58.4(4) 22 . . . ? O1 Cu1 N3 C3 29.6(4) . . . . ? O1 Cu1 N3 C3 -150.4(4) 22 . . . ? C4 N1 C2 C1 -86.2(5) . . . . ? N2 N1 C2 C1 91.3(5) . . . . ? C1 C1 C2 N1 -60.0(6) 21_755 . . . ? N1 N2 C3 N3 -1.2(6) . . . . ? C4 N3 C3 N2 0.8(5) . . . . ? Cu1 N3 C3 N2 178.5(3) . . . . ? N2 N1 C4 N3 -0.6(4) . . . . ? C2 N1 C4 N3 177.2(3) . . . . ? C3 N3 C4 N1 -0.1(4) . . . . ? Cu1 N3 C4 N1 -177.8(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1W O2 0.919(19) 1.92(2) 2.824(6) 166(5) . O1 H1W O5 0.919(19) 1.98(3) 2.855(19) 159(5) 12_544 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.34 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.642 _refine_diff_density_min -0.564 _refine_diff_density_rms 0.075 ###======The End of CIF data_Cu_btb_NO3 #(5) _database_code_depnum_ccdc_archive 'CCDC 810495' #TrackingRef '- Cubtb-CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H28 Cu N14 O8' _chemical_formula_weight 608.06 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Fddd loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/4, z+1/4' 'x+1/4, -y, z+1/4' '-x+1/4, -y+3/4, z+1/2' 'x, y+1/2, z+1/2' '-x, y+3/4, z+3/4' 'x+1/4, -y+1/2, z+3/4' '-x+1/4, -y+5/4, z+1' 'x+1/2, y, z+1/2' '-x+1/2, y+1/4, z+3/4' 'x+3/4, -y, z+3/4' '-x+3/4, -y+3/4, z+1' 'x+1/2, y+1/2, z' '-x+1/2, y+3/4, z+1/4' 'x+3/4, -y+1/2, z+1/4' '-x+3/4, -y+5/4, z+1/2' '-x, -y, -z' 'x, -y-1/4, -z-1/4' '-x-1/4, y, -z-1/4' 'x-1/4, y-3/4, -z-1/2' '-x, -y+1/2, -z+1/2' 'x, -y+1/4, -z+1/4' '-x-1/4, y+1/2, -z+1/4' 'x-1/4, y-1/4, -z' '-x+1/2, -y, -z+1/2' 'x+1/2, -y-1/4, -z+1/4' '-x+1/4, y, -z+1/4' 'x+1/4, y-3/4, -z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/4, -z-1/4' '-x+1/4, y+1/2, -z-1/4' 'x+1/4, y-1/4, -z-1/2' _cell_length_a 12.887(2) _cell_length_b 17.043(3) _cell_length_c 24.799(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5446.6(15) _cell_formula_units_Z 8 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 4472 _cell_measurement_theta_min 3.1631 _cell_measurement_theta_max 25.3491 _exptl_crystal_description Block _exptl_crystal_colour blue _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.483 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2520 _exptl_absorpt_coefficient_mu 0.869 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.6705 _exptl_absorpt_correction_T_max 0.8735 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(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 'Rigaku Mercury CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 12507 _diffrn_reflns_av_R_equivalents 0.0496 _diffrn_reflns_av_sigmaI/netI 0.0248 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 3.16 _diffrn_reflns_theta_max 25.33 _reflns_number_total 1237 _reflns_number_gt 1185 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2000)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2000)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1101P)^2^+28.8567P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1237 _refine_ls_number_parameters 99 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0758 _refine_ls_R_factor_gt 0.0726 _refine_ls_wR_factor_ref 0.2107 _refine_ls_wR_factor_gt 0.2078 _refine_ls_goodness_of_fit_ref 1.315 _refine_ls_restrained_S_all 1.315 _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 0.6250 0.1250 0.1250 0.0257(4) Uani 1 4 d S . . O1 O 0.6250 -0.0159(3) 0.1250 0.0379(12) Uani 1 2 d SD . . O2 O 0.9304(6) 0.4214(5) 0.1465(3) 0.117(3) Uani 1 1 d . . . O3 O 0.7909(11) 0.3794(9) 0.1063(6) 0.048(4) Uiso 0.25 1 d PD . . O4 O 0.8750 0.3750 0.0771(10) 0.069(6) Uiso 0.30 2 d SP . . O5 O 0.914(2) 0.3025(15) 0.1305(10) 0.020(5) Uiso 0.10 1 d P . . N1 N 0.8318(3) 0.1618(2) 0.24903(16) 0.0357(10) Uani 1 1 d . . . N2 N 0.8708(4) 0.0914(3) 0.2324(2) 0.0496(13) Uani 1 1 d . . . N3 N 0.7354(3) 0.12568(19) 0.18247(15) 0.0297(9) Uani 1 1 d . . . N4 N 0.8750 0.3750 0.1249(2) 0.0339(13) Uani 1 2 d SD . . C1 C 0.9573(5) 0.2662(4) 0.2674(3) 0.0644(18) Uani 1 1 d . . . H1A H 0.9894 0.2960 0.2973 0.077 Uiso 1 1 calc R . . H1B H 0.9166 0.3039 0.2456 0.077 Uiso 1 1 calc R . . C2 C 0.8847(4) 0.2082(3) 0.2908(2) 0.0466(13) Uani 1 1 d . . . H2A H 0.9235 0.1725 0.3149 0.056 Uiso 1 1 calc R . . H2B H 0.8321 0.2360 0.3128 0.056 Uiso 1 1 calc R . . C3 C 0.8105(4) 0.0723(3) 0.1927(2) 0.0427(12) Uani 1 1 d . . . H3A H 0.8182 0.0251 0.1728 0.051 Uiso 1 1 calc R . . C4 C 0.7518(3) 0.1807(3) 0.21900(17) 0.0301(10) Uani 1 1 d . . . H4A H 0.7117 0.2271 0.2229 0.036 Uiso 1 1 calc R . . H1W H 0.568(3) -0.050(3) 0.126(2) 0.036 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0176(6) 0.0287(7) 0.0306(7) 0.000 0.000 0.000 O1 0.031(3) 0.024(2) 0.058(3) 0.000 0.003(2) 0.000 O2 0.117(6) 0.122(5) 0.111(5) 0.018(5) -0.010(5) -0.071(5) N1 0.036(2) 0.033(2) 0.038(2) -0.0008(16) -0.0064(17) -0.0006(17) N2 0.047(3) 0.035(2) 0.067(3) -0.001(2) -0.027(2) 0.004(2) N3 0.0238(19) 0.0282(18) 0.037(2) 0.0009(15) -0.0022(16) -0.0009(14) N4 0.022(3) 0.039(3) 0.040(3) 0.000 0.000 -0.011(2) C1 0.063(4) 0.071(4) 0.059(4) -0.017(3) -0.013(3) -0.021(3) C2 0.054(3) 0.049(3) 0.037(3) -0.002(2) -0.015(2) -0.008(2) C3 0.036(3) 0.033(2) 0.058(3) -0.006(2) -0.016(2) 0.006(2) C4 0.028(2) 0.032(2) 0.030(2) -0.0008(17) -0.0012(18) 0.0006(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N3 2.014(4) 27_655 ? Cu1 N3 2.014(4) . ? Cu1 N3 2.014(4) 22 ? Cu1 N3 2.014(4) 8_644 ? Cu1 O1 2.402(5) 22 ? Cu1 O1 2.402(5) . ? O1 H1W 0.93(2) . ? O2 N4 1.192(7) . ? O3 N4 1.180(13) . ? O4 N4 1.18(3) . ? O5 N4 1.34(3) . ? N1 C4 1.312(6) . ? N1 N2 1.363(6) . ? N1 C2 1.471(6) . ? N2 C3 1.296(7) . ? N3 C4 1.321(6) . ? N3 C3 1.352(6) . ? N4 O3 1.180(13) 12_654 ? N4 O2 1.192(7) 12_654 ? N4 O5 1.34(3) 12_654 ? C1 C2 1.480(9) . ? C1 C1 1.504(13) 21_755 ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 H3A 0.9500 . ? C4 H4A 0.9500 . ? 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 N3 Cu1 N3 179.34(19) 27_655 . ? N3 Cu1 N3 89.9(2) 27_655 22 ? N3 Cu1 N3 90.1(2) . 22 ? N3 Cu1 N3 90.1(2) 27_655 8_644 ? N3 Cu1 N3 89.9(2) . 8_644 ? N3 Cu1 N3 179.34(19) 22 8_644 ? N3 Cu1 O1 89.67(9) 27_655 22 ? N3 Cu1 O1 89.67(9) . 22 ? N3 Cu1 O1 90.33(9) 22 22 ? N3 Cu1 O1 90.33(9) 8_644 22 ? N3 Cu1 O1 90.33(9) 27_655 . ? N3 Cu1 O1 90.33(9) . . ? N3 Cu1 O1 89.67(9) 22 . ? N3 Cu1 O1 89.67(9) 8_644 . ? O1 Cu1 O1 180.0 22 . ? Cu1 O1 H1W 128(3) . . ? N4 O2 O3 54.3(7) . 12_654 ? N4 O2 O5 63.1(11) . 12_654 ? O3 O2 O5 103.7(13) 12_654 12_654 ? N4 O3 O4 56.6(12) . . ? N4 O3 O2 55.1(7) . 12_654 ? O4 O3 O2 98.2(12) . 12_654 ? N4 O3 O5 61.1(13) . 12_654 ? O4 O3 O5 86.8(15) . 12_654 ? O2 O3 O5 95.7(14) 12_654 12_654 ? N4 O4 O3 56.3(11) . 12_654 ? N4 O4 O3 56.3(11) . . ? O3 O4 O3 113(2) 12_654 . ? N4 O5 O2 52.4(11) . 12_654 ? N4 O5 O3 50.3(11) . 12_654 ? O2 O5 O3 102.7(18) 12_654 12_654 ? C4 N1 N2 109.6(4) . . ? C4 N1 C2 129.1(4) . . ? N2 N1 C2 121.0(4) . . ? C3 N2 N1 103.3(4) . . ? C4 N3 C3 103.5(4) . . ? C4 N3 Cu1 127.1(3) . . ? C3 N3 Cu1 129.4(3) . . ? O3 N4 O3 134.1(17) . 12_654 ? O3 N4 O4 67.0(9) . . ? O3 N4 O4 67.0(9) 12_654 . ? O3 N4 O2 133.1(9) . . ? O3 N4 O2 70.6(9) 12_654 . ? O4 N4 O2 116.7(4) . . ? O3 N4 O2 70.6(9) . 12_654 ? O3 N4 O2 133.1(9) 12_654 12_654 ? O4 N4 O2 116.7(4) . 12_654 ? O2 N4 O2 126.5(9) . 12_654 ? O3 N4 O5 68.5(14) . 12_654 ? O3 N4 O5 116.5(14) 12_654 12_654 ? O4 N4 O5 95.9(11) . 12_654 ? O2 N4 O5 64.5(13) . 12_654 ? O2 N4 O5 109.7(12) 12_654 12_654 ? O3 N4 O5 116.5(14) . . ? O3 N4 O5 68.5(14) 12_654 . ? O4 N4 O5 95.9(11) . . ? O2 N4 O5 109.7(12) . . ? O2 N4 O5 64.5(13) 12_654 . ? O5 N4 O5 168(2) 12_654 . ? C2 C1 C1 116.3(7) . 21_755 ? C2 C1 H1A 108.2 . . ? C1 C1 H1A 108.2 21_755 . ? C2 C1 H1B 108.2 . . ? C1 C1 H1B 108.2 21_755 . ? H1A C1 H1B 107.4 . . ? N1 C2 C1 112.1(5) . . ? N1 C2 H2A 109.2 . . ? C1 C2 H2A 109.2 . . ? N1 C2 H2B 109.2 . . ? C1 C2 H2B 109.2 . . ? H2A C2 H2B 107.9 . . ? N2 C3 N3 113.7(5) . . ? N2 C3 H3A 123.1 . . ? N3 C3 H3A 123.1 . . ? N1 C4 N3 109.9(4) . . ? N1 C4 H4A 125.1 . . ? N3 C4 H4A 125.1 . . ? 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 O2 O3 O4 N4 -38.1(5) 12_654 . . . ? N4 O3 O4 O3 0.0 . . . 12_654 ? O2 O3 O4 O3 -38.1(5) 12_654 . . 12_654 ? C4 N1 N2 C3 -0.1(6) . . . . ? C2 N1 N2 C3 -174.1(5) . . . . ? N3 Cu1 N3 C4 118.0(4) 22 . . . ? N3 Cu1 N3 C4 -62.6(4) 8_644 . . . ? O1 Cu1 N3 C4 27.7(4) 22 . . . ? O1 Cu1 N3 C4 -152.3(4) . . . . ? N3 Cu1 N3 C3 -60.8(4) 22 . . . ? N3 Cu1 N3 C3 118.5(5) 8_644 . . . ? O1 Cu1 N3 C3 -151.2(4) 22 . . . ? O1 Cu1 N3 C3 28.8(4) . . . . ? C4 N1 C2 C1 -79.8(7) . . . . ? N2 N1 C2 C1 93.0(7) . . . . ? C1 C1 C2 N1 -58.9(9) 21_755 . . . ? N1 N2 C3 N3 0.3(7) . . . . ? C4 N3 C3 N2 -0.4(6) . . . . ? Cu1 N3 C3 N2 178.7(4) . . . . ? N2 N1 C4 N3 -0.1(6) . . . . ? C2 N1 C4 N3 173.3(5) . . . . ? C3 N3 C4 N1 0.3(5) . . . . ? Cu1 N3 C4 N1 -178.8(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1W O2 0.93(2) 1.91(3) 2.778(7) 154(5) 13_445 O1 H1W O3 0.93(2) 2.02(3) 2.920(15) 164(5) 8_644 _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 25.33 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.852 _refine_diff_density_min -0.583 _refine_diff_density_rms 0.097 ###======The End of CIF data_Cu_btb_bdc #(6) _database_code_depnum_ccdc_archive 'CCDC 810496' #TrackingRef '- Cubtb-CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H16 Cu N6 O4' _chemical_formula_sum 'C16 H16 Cu N6 O4' _chemical_formula_weight 419.89 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' 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 C2/c _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 16.103(4) _cell_length_b 8.6062(19) _cell_length_c 13.525(3) _cell_angle_alpha 90.00 _cell_angle_beta 112.305(5) _cell_angle_gamma 90.00 _cell_volume 1734.1(7) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 2960 _cell_measurement_theta_min 3.2542 _cell_measurement_theta_max 25.3491 _exptl_crystal_description Block _exptl_crystal_colour blue _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.608 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 860 _exptl_absorpt_coefficient_mu 1.297 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.5633 _exptl_absorpt_correction_T_max 0.8599 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _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 'Rigaku Mercury CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 8090 _diffrn_reflns_av_R_equivalents 0.0280 _diffrn_reflns_av_sigmaI/netI 0.0217 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.26 _diffrn_reflns_theta_max 25.33 _reflns_number_total 1584 _reflns_number_gt 1469 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2000)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2000)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0549P)^2^+2.5325P] 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 1584 _refine_ls_number_parameters 124 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0378 _refine_ls_R_factor_gt 0.0335 _refine_ls_wR_factor_ref 0.0924 _refine_ls_wR_factor_gt 0.0892 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _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 0.0000 0.0000 0.02267(17) Uani 1 2 d S . . O1 O 0.47416(11) 0.2065(2) -0.06744(12) 0.0279(4) Uani 1 1 d . . . O2 O 0.56303(13) 0.1013(2) -0.13901(13) 0.0368(5) Uani 1 1 d . . . N1 N 0.71450(14) 0.1353(3) 0.26800(16) 0.0329(5) Uani 1 1 d . . . N2 N 0.73211(19) 0.2317(3) 0.1993(2) 0.0590(8) Uani 1 1 d . . . N3 N 0.61320(13) 0.0805(2) 0.11254(15) 0.0289(5) Uani 1 1 d . . . C1 C 0.72307(19) 0.2450(4) 0.4402(2) 0.0407(7) Uani 1 1 d . . . H1A H 0.6630 0.2049 0.4280 0.049 Uiso 1 1 calc R . . H1B H 0.7161 0.3496 0.4094 0.049 Uiso 1 1 calc R . . C2 C 0.76663(18) 0.1420(3) 0.38381(19) 0.0379(6) Uani 1 1 d . . . H2A H 0.8270 0.1812 0.3966 0.046 Uiso 1 1 calc R . . H2B H 0.7727 0.0369 0.4136 0.046 Uiso 1 1 calc R . . C3 C 0.6697(2) 0.1935(4) 0.1072(2) 0.0515(9) Uani 1 1 d . . . H3A H 0.6646 0.2409 0.0425 0.062 Uiso 1 1 calc R . . C4 C 0.64461(16) 0.0466(3) 0.21592(19) 0.0286(5) Uani 1 1 d . . . H4A H 0.6207 -0.0294 0.2475 0.034 Uiso 1 1 calc R . . C5 C 0.50399(15) 0.3549(3) -0.19663(18) 0.0248(5) Uani 1 1 d . . . C6 C 0.50705(19) 0.4968(3) -0.1454(2) 0.0317(6) Uani 1 1 d . . . H6A H 0.5117 0.4975 -0.0740 0.038 Uiso 1 1 calc R . . C7 C 0.50338(18) 0.6365(3) -0.1976(2) 0.0351(6) Uani 1 1 d . . . H7A H 0.5055 0.7309 -0.1619 0.042 Uiso 1 1 calc R . . C8 C 0.51511(16) 0.2092(3) -0.13202(18) 0.0270(5) 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 0.0278(3) 0.0247(3) 0.0134(2) -0.00103(14) 0.00545(18) -0.00073(15) O1 0.0337(9) 0.0309(9) 0.0185(8) 0.0020(7) 0.0091(7) 0.0013(7) O2 0.0549(11) 0.0341(10) 0.0254(9) 0.0045(7) 0.0198(8) 0.0124(9) N1 0.0334(12) 0.0394(12) 0.0197(10) -0.0001(9) 0.0032(9) -0.0067(10) N2 0.0638(17) 0.0701(19) 0.0304(13) 0.0073(12) 0.0036(13) -0.0373(15) N3 0.0345(11) 0.0302(11) 0.0192(10) -0.0015(8) 0.0069(8) -0.0051(9) C1 0.0376(15) 0.0498(17) 0.0240(14) -0.0034(12) -0.0002(12) -0.0009(13) C2 0.0386(15) 0.0445(16) 0.0189(13) -0.0012(11) -0.0024(11) -0.0021(12) C3 0.0562(19) 0.064(2) 0.0249(14) 0.0085(13) 0.0050(13) -0.0279(16) C4 0.0287(13) 0.0339(13) 0.0192(12) -0.0005(10) 0.0048(10) -0.0038(11) C5 0.0264(12) 0.0268(12) 0.0196(11) -0.0006(9) 0.0070(9) -0.0006(9) C6 0.0382(15) 0.0336(15) 0.0247(13) -0.0068(10) 0.0136(12) -0.0003(10) C7 0.0385(14) 0.0256(13) 0.0417(14) -0.0064(11) 0.0158(12) -0.0014(11) C8 0.0332(13) 0.0303(13) 0.0140(11) -0.0032(9) 0.0049(10) -0.0029(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 1.9685(17) . ? Cu1 O1 1.9685(17) 5_655 ? Cu1 N3 2.0034(19) 5_655 ? Cu1 N3 2.0034(19) . ? O1 C8 1.279(3) . ? O2 C8 1.234(3) . ? N1 C4 1.320(3) . ? N1 N2 1.353(3) . ? N1 C2 1.471(3) . ? N2 C3 1.312(4) . ? N3 C4 1.326(3) . ? N3 C3 1.352(4) . ? C1 C2 1.505(4) . ? C1 C1 1.521(5) 7_656 ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C3 H3A 0.9400 . ? C4 H4A 0.9400 . ? C5 C6 1.395(3) . ? C5 C5 1.400(5) 2_654 ? C5 C8 1.499(3) . ? C6 C7 1.384(4) . ? C6 H6A 0.9400 . ? C7 C7 1.378(5) 2_654 ? C7 H7A 0.9400 . ? 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 180.00(10) . 5_655 ? O1 Cu1 N3 89.36(8) . 5_655 ? O1 Cu1 N3 90.64(8) 5_655 5_655 ? O1 Cu1 N3 90.64(8) . . ? O1 Cu1 N3 89.36(8) 5_655 . ? N3 Cu1 N3 180.00(17) 5_655 . ? C8 O1 Cu1 105.08(15) . . ? C4 N1 N2 110.3(2) . . ? C4 N1 C2 128.1(2) . . ? N2 N1 C2 121.6(2) . . ? C3 N2 N1 102.3(2) . . ? C4 N3 C3 102.7(2) . . ? C4 N3 Cu1 126.71(17) . . ? C3 N3 Cu1 130.14(18) . . ? C2 C1 C1 112.6(3) . 7_656 ? C2 C1 H1A 109.1 . . ? C1 C1 H1A 109.1 7_656 . ? C2 C1 H1B 109.1 . . ? C1 C1 H1B 109.1 7_656 . ? H1A C1 H1B 107.8 . . ? N1 C2 C1 112.0(2) . . ? N1 C2 H2A 109.2 . . ? C1 C2 H2A 109.2 . . ? N1 C2 H2B 109.2 . . ? C1 C2 H2B 109.2 . . ? H2A C2 H2B 107.9 . . ? N2 C3 N3 114.7(3) . . ? N2 C3 H3A 122.6 . . ? N3 C3 H3A 122.6 . . ? N1 C4 N3 110.0(2) . . ? N1 C4 H4A 125.0 . . ? N3 C4 H4A 125.0 . . ? C6 C5 C5 118.93(15) . 2_654 ? C6 C5 C8 117.9(2) . . ? C5 C5 C8 123.02(13) 2_654 . ? C7 C6 C5 121.4(3) . . ? C7 C6 H6A 119.3 . . ? C5 C6 H6A 119.3 . . ? C7 C7 C6 119.70(16) 2_654 . ? C7 C7 H7A 120.1 2_654 . ? C6 C7 H7A 120.1 . . ? O2 C8 O1 122.5(2) . . ? O2 C8 C5 121.6(2) . . ? O1 C8 C5 115.8(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 N3 Cu1 O1 C8 -92.78(15) 5_655 . . . ? N3 Cu1 O1 C8 87.22(15) . . . . ? C4 N1 N2 C3 0.0(4) . . . . ? C2 N1 N2 C3 -177.3(3) . . . . ? O1 Cu1 N3 C4 139.5(2) . . . . ? O1 Cu1 N3 C4 -40.5(2) 5_655 . . . ? O1 Cu1 N3 C3 -31.3(3) . . . . ? O1 Cu1 N3 C3 148.7(3) 5_655 . . . ? C4 N1 C2 C1 -83.1(3) . . . . ? N2 N1 C2 C1 93.6(3) . . . . ? C1 C1 C2 N1 -179.2(3) 7_656 . . . ? N1 N2 C3 N3 0.5(4) . . . . ? C4 N3 C3 N2 -0.7(4) . . . . ? Cu1 N3 C3 N2 171.7(2) . . . . ? N2 N1 C4 N3 -0.4(3) . . . . ? C2 N1 C4 N3 176.6(2) . . . . ? C3 N3 C4 N1 0.6(3) . . . . ? Cu1 N3 C4 N1 -172.16(17) . . . . ? C5 C5 C6 C7 -0.7(5) 2_654 . . . ? C8 C5 C6 C7 175.6(2) . . . . ? C5 C6 C7 C7 0.0(5) . . . 2_654 ? Cu1 O1 C8 O2 -3.6(3) . . . . ? Cu1 O1 C8 C5 178.44(15) . . . . ? C6 C5 C8 O2 -136.5(3) . . . . ? C5 C5 C8 O2 39.7(4) 2_654 . . . ? C6 C5 C8 O1 41.4(3) . . . . ? C5 C5 C8 O1 -142.4(3) 2_654 . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.33 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.265 _refine_diff_density_min -0.336 _refine_diff_density_rms 0.055 ###======The End of CIF data_Cu_btb_btec #(7) _database_code_depnum_ccdc_archive 'CCDC 810497' #TrackingRef '- Cubtb-CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H24.50 Cu2 N6 O12.50' _chemical_formula_weight 664.03 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.5798(9) _cell_length_b 8.78490(10) _cell_length_c 19.056(3) _cell_angle_alpha 94.154(11) _cell_angle_beta 96.89 _cell_angle_gamma 112.580(8) _cell_volume 1153.4(2) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 4026 _cell_measurement_theta_min 3.0312 _cell_measurement_theta_max 25.3491 _exptl_crystal_description Block _exptl_crystal_colour Blue _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.912 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 677 _exptl_absorpt_coefficient_mu 1.928 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.5127 _exptl_absorpt_correction_T_max 0.7608 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _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 'Rigaku Mercury CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 11368 _diffrn_reflns_av_R_equivalents 0.0371 _diffrn_reflns_av_sigmaI/netI 0.0515 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 25.35 _reflns_number_total 4190 _reflns_number_gt 3405 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2000)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2000)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0594P)^2^+2.9420P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4190 _refine_ls_number_parameters 378 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.0649 _refine_ls_R_factor_gt 0.0483 _refine_ls_wR_factor_ref 0.1315 _refine_ls_wR_factor_gt 0.1200 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.075 _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 0.68000(8) 0.85471(7) 0.83359(3) 0.01719(18) Uani 1 1 d . . . Cu2 Cu -0.00510(8) 0.70464(7) 0.65110(3) 0.01993(18) Uani 1 1 d . . . O1 O 0.6958(6) 0.6989(4) 0.7411(2) 0.0406(11) Uani 1 1 d . . . O2 O 0.7333(4) 0.5430(4) 0.65326(18) 0.0219(7) Uani 1 1 d . . . O3 O 0.0833(5) 0.5378(4) 0.68822(19) 0.0253(8) Uani 1 1 d . . . O4 O 0.3364(5) 0.5922(5) 0.6301(2) 0.0330(9) Uani 1 1 d . . . O5 O -0.1000(4) 0.0342(4) 0.80869(17) 0.0191(7) Uani 1 1 d . . . O6 O 0.0984(6) -0.0988(6) 0.8193(3) 0.0708(18) Uani 1 1 d . . . O7 O 0.5060(4) -0.0515(4) 0.78044(17) 0.0200(7) Uani 1 1 d . . . O8 O 0.5280(6) 0.0884(5) 0.88566(19) 0.0358(9) Uani 1 1 d . . . O9 O 0.8483(5) 0.8266(6) 0.9167(2) 0.0456(12) Uani 1 1 d D . . O10 O 0.2721(5) 0.8540(4) 0.65205(19) 0.0247(8) Uani 1 1 d D . . O11 O -0.0610(7) 0.6196(5) 0.5269(2) 0.0437(11) Uani 1 1 d D . . O12 O 0.5000 0.5000 0.5000 0.073(2) Uani 1 2 d S . . O13 O 1.2286(12) 1.1271(9) 0.9546(4) 0.109(2) Uani 1 1 d . . . H13 H 1.3018 1.2224 0.9733 0.164 Uiso 1 1 calc R . . N1 N 0.1836(6) 0.5197(5) 0.8901(2) 0.0203(9) Uani 1 1 d . . . N2 N 0.3072(6) 0.4492(5) 0.9149(2) 0.0255(9) Uani 1 1 d . . . N3 N 0.4623(5) 0.6789(5) 0.8661(2) 0.0199(9) Uani 1 1 d . . . N4 N -0.2079(6) 1.0658(5) 0.6023(2) 0.0201(9) Uani 1 1 d . . . N5 N -0.0397(6) 1.1236(5) 0.5741(2) 0.0238(9) Uani 1 1 d . . . N6 N -0.0679(6) 0.8982(5) 0.6271(2) 0.0205(9) Uani 1 1 d . . . C1 C -0.0467(7) 0.4204(6) 0.9741(3) 0.0263(11) Uani 1 1 d . . . H1A H 0.0084 0.3415 0.9892 0.032 Uiso 1 1 calc R . . H1B H -0.1855 0.3710 0.9764 0.032 Uiso 1 1 calc R . . C2 C -0.0211(7) 0.4440(6) 0.8975(3) 0.0261(11) Uani 1 1 d . . . H2A H -0.0826 0.3359 0.8676 0.031 Uiso 1 1 calc R . . H2B H -0.0858 0.5151 0.8805 0.031 Uiso 1 1 calc R . . C3 C 0.4712(7) 0.5486(6) 0.8996(3) 0.0273(12) Uani 1 1 d . . . H3A H 0.5866 0.5326 0.9107 0.033 Uiso 1 1 calc R . . C4 C 0.2786(7) 0.6564(6) 0.8617(3) 0.0234(11) Uani 1 1 d . . . H4A H 0.2235 0.7258 0.8418 0.028 Uiso 1 1 calc R . . C5 C -0.4487(7) 1.0938(6) 0.5116(3) 0.0258(11) Uani 1 1 d . . . H5A H -0.3516 1.1413 0.4809 0.031 Uiso 1 1 calc R . . H5B H -0.5437 1.1440 0.5044 0.031 Uiso 1 1 calc R . . C6 C -0.3498(7) 1.1402(6) 0.5889(3) 0.0237(11) Uani 1 1 d . . . H6A H -0.2846 1.2614 0.5996 0.028 Uiso 1 1 calc R . . H6B H -0.4471 1.1012 0.6202 0.028 Uiso 1 1 calc R . . C7 C 0.0395(7) 1.0193(6) 0.5916(3) 0.0211(10) Uani 1 1 d . . . H7A H 0.1602 1.0282 0.5803 0.025 Uiso 1 1 calc R . . C8 C -0.2228(7) 0.9324(6) 0.6331(2) 0.0218(10) Uani 1 1 d . . . H8A H -0.3265 0.8711 0.6558 0.026 Uiso 1 1 calc R . . C9 C 0.4847(6) 0.4154(5) 0.7209(2) 0.0154(9) Uani 1 1 d . . . C10 C 0.2927(6) 0.4009(5) 0.7134(2) 0.0165(9) Uani 1 1 d . . . C11 C 0.1596(6) 0.2733(5) 0.7408(2) 0.0153(9) Uani 1 1 d . . . H11A H 0.0309 0.2641 0.7362 0.018 Uiso 1 1 calc R . . C12 C 0.2092(6) 0.1573(5) 0.7751(2) 0.0173(10) Uani 1 1 d . . . C13 C 0.4021(6) 0.1713(5) 0.7816(2) 0.0154(9) Uani 1 1 d . . . C14 C 0.5363(6) 0.3000(5) 0.7534(2) 0.0166(9) Uani 1 1 d . . . H14A H 0.6645 0.3084 0.7565 0.020 Uiso 1 1 calc R . . C15 C 0.6469(6) 0.5663(5) 0.7025(3) 0.0167(10) Uani 1 1 d . . . C16 C 0.2338(7) 0.5182(6) 0.6742(3) 0.0201(10) Uani 1 1 d . . . C17 C 0.0580(7) 0.0182(6) 0.8033(3) 0.0259(11) Uani 1 1 d . . . C18 C 0.4786(6) 0.0602(6) 0.8204(3) 0.0203(10) Uani 1 1 d . . . C19 C 1.2909(18) 0.9989(14) 0.9903(5) 0.116(4) Uani 1 1 d . . . H19A H 1.3800 1.0529 1.0341 0.175 Uiso 1 1 calc R . . H19B H 1.3543 0.9539 0.9582 0.175 Uiso 1 1 calc R . . H19C H 1.1777 0.9095 1.0008 0.175 Uiso 1 1 calc R . . H1W H 0.833(14) 0.872(13) 0.951(4) 0.140 Uiso 1 1 d D . . H2W H 0.958(9) 0.873(12) 0.907(5) 0.140 Uiso 1 1 d D . . H3W H 0.317(15) 0.783(11) 0.643(6) 0.140 Uiso 1 1 d D . . H4W H 0.348(13) 0.904(12) 0.694(4) 0.140 Uiso 1 1 d D . . H5W H -0.052(16) 0.673(12) 0.492(4) 0.140 Uiso 1 1 d D . . H6W H 0.006(12) 0.571(10) 0.523(5) 0.140 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0145(3) 0.0173(3) 0.0211(3) 0.0074(2) 0.0044(2) 0.0064(2) Cu2 0.0163(3) 0.0177(3) 0.0303(4) 0.0105(3) 0.0068(2) 0.0094(2) O1 0.062(3) 0.0173(19) 0.032(2) -0.0019(16) 0.028(2) -0.0012(18) O2 0.0179(17) 0.0172(16) 0.036(2) 0.0063(15) 0.0174(15) 0.0087(14) O3 0.0196(18) 0.0250(18) 0.042(2) 0.0186(16) 0.0137(15) 0.0152(15) O4 0.038(2) 0.045(2) 0.039(2) 0.0275(19) 0.0232(18) 0.0321(19) O5 0.0119(16) 0.0145(16) 0.0331(19) 0.0082(14) 0.0085(13) 0.0056(13) O6 0.039(3) 0.051(3) 0.162(5) 0.079(3) 0.058(3) 0.038(2) O7 0.0205(17) 0.0188(16) 0.0250(18) 0.0073(14) 0.0041(14) 0.0115(14) O8 0.053(2) 0.039(2) 0.026(2) 0.0058(17) -0.0012(18) 0.031(2) O9 0.021(2) 0.077(3) 0.043(2) 0.035(2) 0.0072(18) 0.018(2) O10 0.0184(18) 0.0216(18) 0.034(2) 0.0081(16) 0.0056(15) 0.0060(15) O11 0.079(3) 0.031(2) 0.032(2) 0.0079(18) 0.021(2) 0.030(2) O12 0.057(5) 0.123(7) 0.050(4) -0.008(4) 0.004(3) 0.052(5) O13 0.138(7) 0.086(5) 0.098(5) 0.022(4) 0.004(5) 0.041(5) N1 0.019(2) 0.023(2) 0.021(2) 0.0061(17) 0.0071(16) 0.0092(17) N2 0.021(2) 0.026(2) 0.032(2) 0.0116(19) 0.0070(18) 0.0099(19) N3 0.021(2) 0.018(2) 0.024(2) 0.0057(17) 0.0080(17) 0.0098(17) N4 0.024(2) 0.019(2) 0.020(2) 0.0040(17) 0.0024(16) 0.0107(17) N5 0.026(2) 0.025(2) 0.026(2) 0.0103(18) 0.0082(18) 0.0142(19) N6 0.026(2) 0.018(2) 0.020(2) 0.0071(17) 0.0041(17) 0.0098(18) C1 0.018(3) 0.025(3) 0.034(3) 0.007(2) 0.010(2) 0.003(2) C2 0.020(3) 0.030(3) 0.027(3) 0.006(2) 0.009(2) 0.005(2) C3 0.026(3) 0.026(3) 0.036(3) 0.012(2) 0.007(2) 0.015(2) C4 0.024(3) 0.025(3) 0.026(3) 0.007(2) 0.005(2) 0.014(2) C5 0.027(3) 0.026(3) 0.030(3) 0.008(2) 0.004(2) 0.016(2) C6 0.027(3) 0.021(2) 0.031(3) 0.006(2) 0.009(2) 0.017(2) C7 0.020(3) 0.023(2) 0.026(3) 0.009(2) 0.006(2) 0.013(2) C8 0.021(3) 0.023(2) 0.022(3) 0.008(2) 0.003(2) 0.009(2) C9 0.014(2) 0.013(2) 0.019(2) 0.0015(18) 0.0045(18) 0.0051(18) C10 0.019(2) 0.013(2) 0.018(2) 0.0004(18) 0.0015(18) 0.0086(19) C11 0.012(2) 0.016(2) 0.019(2) 0.0001(18) 0.0036(17) 0.0072(18) C12 0.017(2) 0.014(2) 0.022(2) 0.0024(19) 0.0045(19) 0.0065(19) C13 0.017(2) 0.016(2) 0.017(2) 0.0023(18) 0.0039(18) 0.0107(19) C14 0.011(2) 0.015(2) 0.026(2) 0.0029(19) 0.0009(18) 0.0069(18) C15 0.012(2) 0.013(2) 0.028(3) 0.005(2) 0.0042(19) 0.0081(19) C16 0.020(3) 0.016(2) 0.026(3) 0.002(2) 0.002(2) 0.009(2) C17 0.015(3) 0.023(3) 0.041(3) 0.013(2) 0.009(2) 0.007(2) C18 0.012(2) 0.016(2) 0.036(3) 0.008(2) 0.006(2) 0.0072(19) C19 0.152(11) 0.108(8) 0.070(6) 0.026(6) 0.010(7) 0.030(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O5 1.942(3) 1_665 ? Cu1 N3 1.980(4) . ? Cu1 O9 2.002(4) . ? Cu1 O7 2.019(3) 1_565 ? Cu1 O1 2.196(4) . ? Cu2 O2 1.954(3) 1_455 ? Cu2 O3 1.972(3) . ? Cu2 O10 2.002(3) . ? Cu2 N6 2.002(4) . ? Cu2 O11 2.366(4) . ? O1 C15 1.230(6) . ? O2 C15 1.255(6) . ? O2 Cu2 1.954(3) 1_655 ? O3 C16 1.273(6) . ? O4 C16 1.257(6) . ? O5 C17 1.273(6) . ? O5 Cu1 1.942(3) 1_445 ? O6 C17 1.228(6) . ? O7 C18 1.293(6) . ? O7 Cu1 2.019(3) 1_545 ? O8 C18 1.233(6) . ? O9 H1W 0.79(4) . ? O9 H2W 0.82(5) . ? O10 H3W 0.83(5) . ? O10 H4W 0.90(5) . ? O11 H5W 0.83(5) . ? O11 H6W 0.78(5) . ? O13 C19 1.548(12) . ? O13 H13 0.8300 . ? N1 C4 1.332(6) . ? N1 N2 1.365(6) . ? N1 C2 1.464(6) . ? N2 C3 1.297(6) . ? N3 C4 1.320(6) . ? N3 C3 1.370(6) . ? N4 C8 1.321(6) . ? N4 N5 1.370(5) . ? N4 C6 1.465(6) . ? N5 C7 1.315(6) . ? N6 C8 1.335(6) . ? N6 C7 1.351(6) . ? C1 C2 1.514(7) . ? C1 C1 1.519(10) 2_567 ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C3 H3A 0.9400 . ? C4 H4A 0.9400 . ? C5 C6 1.520(7) . ? C5 C5 1.532(10) 2_476 ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C7 H7A 0.9400 . ? C8 H8A 0.9400 . ? C9 C14 1.379(6) . ? C9 C10 1.399(6) . ? C9 C15 1.520(6) . ? C10 C11 1.375(6) . ? C10 C16 1.485(6) . ? C11 C12 1.392(6) . ? C11 H11A 0.9400 . ? C12 C13 1.409(6) . ? C12 C17 1.504(6) . ? C13 C14 1.392(6) . ? C13 C18 1.508(6) . ? C14 H14A 0.9400 . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C19 H19C 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O5 Cu1 N3 175.92(15) 1_665 . ? O5 Cu1 O9 90.89(15) 1_665 . ? N3 Cu1 O9 86.17(16) . . ? O5 Cu1 O7 88.21(13) 1_665 1_565 ? N3 Cu1 O7 93.40(15) . 1_565 ? O9 Cu1 O7 157.12(18) . 1_565 ? O5 Cu1 O1 87.37(13) 1_665 . ? N3 Cu1 O1 96.16(15) . . ? O9 Cu1 O1 106.45(19) . . ? O7 Cu1 O1 96.35(15) 1_565 . ? O2 Cu2 O3 85.95(13) 1_455 . ? O2 Cu2 O10 174.52(14) 1_455 . ? O3 Cu2 O10 88.57(14) . . ? O2 Cu2 N6 99.01(15) 1_455 . ? O3 Cu2 N6 170.88(16) . . ? O10 Cu2 N6 86.45(15) . . ? O2 Cu2 O11 87.49(15) 1_455 . ? O3 Cu2 O11 101.06(15) . . ? O10 Cu2 O11 93.32(16) . . ? N6 Cu2 O11 86.86(15) . . ? C15 O1 Cu1 153.4(3) . . ? C15 O2 Cu2 118.4(3) . 1_655 ? C16 O3 Cu2 124.4(3) . . ? C17 O5 Cu1 121.3(3) . 1_445 ? C18 O7 Cu1 112.4(3) . 1_545 ? Cu1 O9 H1W 107(9) . . ? Cu1 O9 H2W 103(8) . . ? H1W O9 H2W 112(6) . . ? Cu2 O10 H3W 100(8) . . ? Cu2 O10 H4W 119(7) . . ? H3W O10 H4W 99(9) . . ? Cu2 O11 H5W 132(8) . . ? Cu2 O11 H6W 103(6) . . ? H5W O11 H6W 106(10) . . ? C19 O13 H13 109.5 . . ? C4 N1 N2 110.2(4) . . ? C4 N1 C2 129.6(4) . . ? N2 N1 C2 120.2(4) . . ? C3 N2 N1 102.7(4) . . ? C4 N3 C3 103.3(4) . . ? C4 N3 Cu1 130.2(3) . . ? C3 N3 Cu1 126.5(3) . . ? C8 N4 N5 110.2(4) . . ? C8 N4 C6 129.3(4) . . ? N5 N4 C6 120.1(4) . . ? C7 N5 N4 102.6(4) . . ? C8 N6 C7 103.8(4) . . ? C8 N6 Cu2 131.7(3) . . ? C7 N6 Cu2 124.2(3) . . ? C2 C1 C1 114.2(5) . 2_567 ? C2 C1 H1A 108.7 . . ? C1 C1 H1A 108.7 2_567 . ? C2 C1 H1B 108.7 . . ? C1 C1 H1B 108.7 2_567 . ? H1A C1 H1B 107.6 . . ? N1 C2 C1 111.7(4) . . ? N1 C2 H2A 109.3 . . ? C1 C2 H2A 109.3 . . ? N1 C2 H2B 109.3 . . ? C1 C2 H2B 109.3 . . ? H2A C2 H2B 107.9 . . ? N2 C3 N3 114.4(4) . . ? N2 C3 H3A 122.8 . . ? N3 C3 H3A 122.8 . . ? N3 C4 N1 109.3(4) . . ? N3 C4 H4A 125.3 . . ? N1 C4 H4A 125.3 . . ? C6 C5 C5 113.9(5) . 2_476 ? C6 C5 H5A 108.8 . . ? C5 C5 H5A 108.8 2_476 . ? C6 C5 H5B 108.8 . . ? C5 C5 H5B 108.8 2_476 . ? H5A C5 H5B 107.7 . . ? N4 C6 C5 110.7(4) . . ? N4 C6 H6A 109.5 . . ? C5 C6 H6A 109.5 . . ? N4 C6 H6B 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 108.1 . . ? N5 C7 N6 114.1(4) . . ? N5 C7 H7A 123.0 . . ? N6 C7 H7A 123.0 . . ? N4 C8 N6 109.4(4) . . ? N4 C8 H8A 125.3 . . ? N6 C8 H8A 125.3 . . ? C14 C9 C10 120.0(4) . . ? C14 C9 C15 117.2(4) . . ? C10 C9 C15 122.3(4) . . ? C11 C10 C9 118.8(4) . . ? C11 C10 C16 120.9(4) . . ? C9 C10 C16 120.2(4) . . ? C10 C11 C12 122.2(4) . . ? C10 C11 H11A 118.9 . . ? C12 C11 H11A 118.9 . . ? C11 C12 C13 118.7(4) . . ? C11 C12 C17 120.3(4) . . ? C13 C12 C17 120.9(4) . . ? C14 C13 C12 119.0(4) . . ? C14 C13 C18 116.4(4) . . ? C12 C13 C18 124.6(4) . . ? C9 C14 C13 121.2(4) . . ? C9 C14 H14A 119.4 . . ? C13 C14 H14A 119.4 . . ? O1 C15 O2 124.5(4) . . ? O1 C15 C9 117.7(4) . . ? O2 C15 C9 117.4(4) . . ? O4 C16 O3 124.6(4) . . ? O4 C16 C10 118.0(4) . . ? O3 C16 C10 117.4(4) . . ? O6 C17 O5 126.2(4) . . ? O6 C17 C12 117.4(4) . . ? O5 C17 C12 116.4(4) . . ? O8 C18 O7 123.8(4) . . ? O8 C18 C13 120.2(4) . . ? O7 C18 C13 115.7(4) . . ? O13 C19 H19A 109.5 . . ? O13 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? O13 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O5 Cu1 O1 C15 173.9(9) 1_665 . . . ? N3 Cu1 O1 C15 -4.0(9) . . . . ? O9 Cu1 O1 C15 83.8(9) . . . . ? O7 Cu1 O1 C15 -98.1(9) 1_565 . . . ? O2 Cu2 O3 C16 147.9(4) 1_455 . . . ? O10 Cu2 O3 C16 -31.8(4) . . . . ? O11 Cu2 O3 C16 61.3(4) . . . . ? C4 N1 N2 C3 -0.2(5) . . . . ? C2 N1 N2 C3 -179.7(4) . . . . ? O9 Cu1 N3 C4 148.1(5) . . . . ? O7 Cu1 N3 C4 -8.9(4) 1_565 . . . ? O1 Cu1 N3 C4 -105.7(4) . . . . ? O9 Cu1 N3 C3 -31.9(4) . . . . ? O7 Cu1 N3 C3 171.0(4) 1_565 . . . ? O1 Cu1 N3 C3 74.3(4) . . . . ? C8 N4 N5 C7 -1.1(5) . . . . ? C6 N4 N5 C7 -174.5(4) . . . . ? O2 Cu2 N6 C8 19.6(5) 1_455 . . . ? O10 Cu2 N6 C8 -159.9(4) . . . . ? O11 Cu2 N6 C8 106.5(4) . . . . ? O2 Cu2 N6 C7 -152.0(4) 1_455 . . . ? O10 Cu2 N6 C7 28.5(4) . . . . ? O11 Cu2 N6 C7 -65.1(4) . . . . ? C4 N1 C2 C1 -125.0(5) . . . . ? N2 N1 C2 C1 54.4(6) . . . . ? C1 C1 C2 N1 57.7(7) 2_567 . . . ? N1 N2 C3 N3 -0.3(6) . . . . ? C4 N3 C3 N2 0.7(6) . . . . ? Cu1 N3 C3 N2 -179.3(3) . . . . ? C3 N3 C4 N1 -0.8(5) . . . . ? Cu1 N3 C4 N1 179.2(3) . . . . ? N2 N1 C4 N3 0.6(6) . . . . ? C2 N1 C4 N3 -180.0(4) . . . . ? C8 N4 C6 C5 -101.2(6) . . . . ? N5 N4 C6 C5 70.7(5) . . . . ? C5 C5 C6 N4 57.7(7) 2_476 . . . ? N4 N5 C7 N6 1.4(5) . . . . ? C8 N6 C7 N5 -1.2(6) . . . . ? Cu2 N6 C7 N5 172.4(3) . . . . ? N5 N4 C8 N6 0.4(5) . . . . ? C6 N4 C8 N6 173.0(4) . . . . ? C7 N6 C8 N4 0.4(5) . . . . ? Cu2 N6 C8 N4 -172.4(3) . . . . ? C14 C9 C10 C11 2.0(7) . . . . ? C15 C9 C10 C11 -170.5(4) . . . . ? C14 C9 C10 C16 -175.9(4) . . . . ? C15 C9 C10 C16 11.6(7) . . . . ? C9 C10 C11 C12 -0.7(7) . . . . ? C16 C10 C11 C12 177.2(4) . . . . ? C10 C11 C12 C13 -0.3(7) . . . . ? C10 C11 C12 C17 -179.0(4) . . . . ? C11 C12 C13 C14 -0.2(7) . . . . ? C17 C12 C13 C14 178.6(4) . . . . ? C11 C12 C13 C18 176.9(4) . . . . ? C17 C12 C13 C18 -4.4(7) . . . . ? C10 C9 C14 C13 -2.5(7) . . . . ? C15 C9 C14 C13 170.4(4) . . . . ? C12 C13 C14 C9 1.5(7) . . . . ? C18 C13 C14 C9 -175.7(4) . . . . ? Cu1 O1 C15 O2 -170.4(6) . . . . ? Cu2 O2 C15 O1 16.0(6) 1_655 . . . ? Cu2 O2 C15 C9 -157.0(3) 1_655 . . . ? C14 C9 C15 O1 -103.5(5) . . . . ? C10 C9 C15 O1 69.2(6) . . . . ? C14 C9 C15 O2 70.0(6) . . . . ? C10 C9 C15 O2 -117.3(5) . . . . ? Cu2 O3 C16 O4 -6.5(7) . . . . ? Cu2 O3 C16 C10 172.8(3) . . . . ? C11 C10 C16 O4 -155.5(5) . . . . ? C9 C10 C16 O4 22.3(7) . . . . ? C11 C10 C16 O3 25.1(6) . . . . ? C9 C10 C16 O3 -157.1(4) . . . . ? Cu1 O5 C17 O6 -7.8(8) 1_445 . . . ? Cu1 O5 C17 C12 172.8(3) 1_445 . . . ? C11 C12 C17 O6 165.1(5) . . . . ? C13 C12 C17 O6 -13.7(8) . . . . ? C11 C12 C17 O5 -15.4(7) . . . . ? C13 C12 C17 O5 165.8(4) . . . . ? Cu1 O7 C18 O8 -10.4(6) 1_545 . . . ? Cu1 O7 C18 C13 162.7(3) 1_545 . . . ? C14 C13 C18 O8 94.5(5) . . . . ? C12 C13 C18 O8 -82.6(6) . . . . ? C14 C13 C18 O7 -78.8(5) . . . . ? C12 C13 C18 O7 104.1(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O9 H1W O13 0.79(4) 1.91(6) 2.628(10) 151(12) 2_777 O9 H2W O6 0.82(5) 2.07(7) 2.744(6) 139(10) 1_665 O9 H2W O13 0.82(5) 2.40(8) 3.030(9) 134(9) . O10 H3W O4 0.83(5) 1.74(6) 2.544(5) 161(11) . O10 H4W O7 0.90(5) 1.84(6) 2.712(5) 164(10) 1_565 O11 H5W N5 0.83(5) 2.20(6) 3.006(6) 162(10) 2_576 O11 H6W O11 0.78(5) 2.07(2) 2.780(8) 150(5) 2_566 O13 H13 N2 0.83 2.34 2.840(8) 119.1 1_665 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.590 _refine_diff_density_min -0.786 _refine_diff_density_rms 0.112 ###======The End of CIF