# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_publication_text _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _publ_contact_author_name 'Dr. Benyong Lou' _publ_contact_author_address ; Department of chemistry and chemical engineering, Minjiang University, Fuzhou, 350108, China ; _publ_contact_author_email lby@mju.edu.cn _publ_contact_author_phone none loop_ _publ_author_name _publ_author_address 'Benyong Lou' ; Department of chemistry and chemical engineering, Minjiang University, Fuzhou, 350108, P.R. China ; 'Yongqin Wei' ; State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou, 350002, P.R. China ; 'Qi Lin' ; Department of chemistry and chemical engineering, Minjiang University, Fuzhou, 350108, P.R. China ; data_I _database_code_depnum_ccdc_archive 'CCDC 838896' #TrackingRef '- complex 1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C20 H28 Cu2 N6 O8), C10 H8 N2, 8(H2 O)' _chemical_formula_sum 'C50 H80 Cu4 N14 O24' _chemical_formula_weight 1515.44 _chemical_absolute_configuration rm 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 orthorhombic _symmetry_space_group_name_H-M I222 _symmetry_space_group_name_Hall I22 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x, -y, -z' '-x, y, -z' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, -z+1/2' '-x+1/2, y+1/2, -z+1/2' _cell_length_a 11.202(10) _cell_length_b 12.897(11) _cell_length_c 28.51(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4118(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4460 _cell_measurement_theta_min 3.1593 _cell_measurement_theta_max 27.5050 _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.222 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1572 _exptl_absorpt_coefficient_mu 1.088 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9123 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'RIGAKU/MSC(2004), CrystalClear Version 1.3.6' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 CCD _diffrn_measurement_method CCD_Profile_fitting _diffrn_detector_area_resol_mean 14.6306 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16027 _diffrn_reflns_av_R_equivalents 0.0632 _diffrn_reflns_av_sigmaI/netI 0.0684 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 3.16 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4729 _reflns_number_gt 3393 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.1026P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.04(3) _refine_ls_number_reflns 4729 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0910 _refine_ls_R_factor_gt 0.0658 _refine_ls_wR_factor_ref 0.1838 _refine_ls_wR_factor_gt 0.1647 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _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 0.14944(6) 0.92412(5) 0.30948(2) 0.0435(2) Uani 1 1 d . . . O1 O 0.2240(5) 0.9308(5) 0.17182(15) 0.0798(16) Uani 1 1 d . . . N1 N 0.2986(4) 1.0054(4) 0.29182(16) 0.0496(11) Uani 1 1 d . . . H1A H 0.2849 1.0753 0.2953 0.060 Uiso 1 1 calc R . . H1B H 0.3609 0.9870 0.3111 0.060 Uiso 1 1 calc R . . C1 C 0.3294(6) 0.9819(6) 0.2420(2) 0.0577(16) Uani 1 1 d . . . H1C H 0.3957 0.9313 0.2410 0.069 Uiso 1 1 calc R . . H1D H 0.3563 1.0461 0.2261 0.069 Uiso 1 1 calc R . . O2 O -0.0161(3) 0.8708(3) 0.30898(13) 0.0516(9) Uani 1 1 d . . . N2 N 0.1346(4) 0.9083(4) 0.24326(14) 0.0421(10) Uani 1 1 d . . . C2 C 0.2205(5) 0.9372(5) 0.21581(19) 0.0479(13) Uani 1 1 d . . . O3 O -0.1602(4) 0.8115(4) 0.26228(14) 0.0571(10) Uani 1 1 d . . . N3 N 0.1543(4) 0.9529(3) 0.37774(14) 0.0429(10) Uani 1 1 d . . . C3 C 0.0292(5) 0.8551(4) 0.22727(18) 0.0418(12) Uani 1 1 d . . . H3 H -0.0095 0.8981 0.2023 0.050 Uiso 1 1 calc R . . O4 O 0.2478(4) 0.7628(4) 0.32125(16) 0.0706(13) Uani 1 1 d . . . N4 N 0.5000 1.0000 0.3746(3) 0.068(2) Uani 1 2 d S . . C4 C -0.0564(5) 0.8454(4) 0.2678(2) 0.0431(12) Uani 1 1 d . . . O5 O 0.4216(11) 0.8196(11) 0.1401(4) 0.203(5) Uiso 1 1 d . . . C5 C 0.0548(5) 0.7478(5) 0.2071(2) 0.0606(17) Uani 1 1 d . . . H5A H 0.1071 0.7544 0.1797 0.091 Uiso 1 1 calc R . . H5B H -0.0204 0.7150 0.1977 0.091 Uiso 1 1 calc R . . H5C H 0.0940 0.7050 0.2310 0.091 Uiso 1 1 calc R . . O6 O 0.3181(13) 1.0933(11) 0.1255(4) 0.249(6) Uiso 1 1 d . . . H4A H 0.2013 0.7056 0.3291 0.298 Uiso 1 1 d R . . H4B H 0.2629 0.7523 0.2914 0.298 Uiso 1 1 d R . . H5E H 0.4322 0.7501 0.1527 0.298 Uiso 1 1 d R . . H6B H 0.2896 1.0403 0.1416 0.298 Uiso 1 1 d R . . H6A H 0.3968 1.0877 0.1284 0.298 Uiso 1 1 d R . . H5D H 0.3360 0.8221 0.1430 0.298 Uiso 1 1 d R . . C6 C 0.1303(6) 0.8786(5) 0.40872(19) 0.0555(16) Uani 1 1 d . . . H6 H 0.1083 0.8121 0.3972 0.067 Uiso 1 1 calc R . . C7 C 0.1355(6) 0.8929(5) 0.45655(19) 0.0553(16) Uani 1 1 d . . . H7 H 0.1197 0.8366 0.4771 0.066 Uiso 1 1 calc R . . C8 C 0.1843(6) 1.0465(5) 0.3951(2) 0.0540(16) Uani 1 1 d . . . H8 H 0.2028 1.1004 0.3736 0.065 Uiso 1 1 calc R . . C9 C 0.1896(5) 1.0677(5) 0.44172(19) 0.0518(14) Uani 1 1 d . . . H9 H 0.2108 1.1352 0.4521 0.062 Uiso 1 1 calc R . . C10 C 0.1637(5) 0.9893(5) 0.47452(17) 0.0448(13) Uani 1 1 d . . . C11 C 0.5293(6) 1.0810(7) 0.3999(2) 0.0693(19) Uani 1 1 d . . . H11 H 0.5525 1.1413 0.3831 0.083 Uiso 1 1 calc R . . C12 C 0.5304(6) 1.0883(7) 0.4482(2) 0.0611(17) Uani 1 1 d . . . H12 H 0.5511 1.1514 0.4633 0.073 Uiso 1 1 calc R . . C13 C 0.5000 1.0000 0.4745(3) 0.048(2) Uani 1 2 d S . . 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 0.0473(3) 0.0503(4) 0.0330(3) -0.0062(3) -0.0007(3) -0.0051(3) O1 0.087(3) 0.117(4) 0.035(2) -0.006(3) 0.008(2) -0.018(4) N1 0.047(2) 0.044(3) 0.058(3) -0.001(2) -0.008(2) -0.003(2) C1 0.056(4) 0.061(4) 0.056(4) 0.002(3) 0.005(3) -0.008(3) O2 0.050(2) 0.067(3) 0.0383(19) -0.016(2) 0.004(2) -0.0059(18) N2 0.046(2) 0.049(3) 0.032(2) -0.0004(19) 0.0036(18) 0.002(2) C2 0.053(3) 0.047(3) 0.044(3) 0.005(3) -0.001(2) -0.003(3) O3 0.048(2) 0.069(3) 0.055(2) -0.019(2) -0.0051(19) -0.013(2) N3 0.040(2) 0.051(3) 0.037(2) -0.0122(19) -0.002(2) -0.002(2) C3 0.047(3) 0.043(3) 0.035(3) -0.006(2) -0.006(2) 0.006(2) O4 0.076(3) 0.078(3) 0.058(3) -0.001(2) 0.008(2) 0.021(3) N4 0.070(5) 0.089(7) 0.046(4) 0.000 0.000 0.009(5) C4 0.042(3) 0.037(3) 0.051(3) -0.014(2) 0.002(2) -0.001(2) C5 0.053(3) 0.060(4) 0.069(4) -0.032(3) 0.000(3) 0.000(3) C6 0.072(4) 0.058(4) 0.037(3) -0.009(3) 0.007(3) -0.020(3) C7 0.062(4) 0.068(4) 0.036(3) -0.011(3) 0.009(3) -0.020(3) C8 0.064(4) 0.055(4) 0.043(3) -0.002(3) -0.003(3) 0.002(3) C9 0.063(3) 0.048(3) 0.045(3) -0.012(3) -0.007(2) 0.004(3) C10 0.045(3) 0.058(3) 0.032(3) -0.008(2) 0.001(2) 0.003(3) C11 0.068(4) 0.096(6) 0.044(3) 0.016(4) -0.004(3) 0.000(4) C12 0.063(4) 0.073(5) 0.048(3) 0.005(3) 0.000(3) 0.003(4) C13 0.037(4) 0.070(6) 0.038(4) 0.000 0.000 0.009(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 N2 1.906(4) . ? Cu1 O2 1.978(4) . ? Cu1 N3 1.982(4) . ? Cu1 N1 2.036(5) . ? Cu1 O4 2.378(5) . ? O1 C2 1.257(7) . ? N1 C1 1.494(7) . ? N1 H1A 0.9200 . ? N1 H1B 0.9200 . ? C1 C2 1.541(8) . ? C1 H1C 0.9900 . ? C1 H1D 0.9900 . ? O2 C4 1.299(6) . ? N2 C2 1.295(7) . ? N2 C3 1.440(7) . ? O3 C4 1.252(7) . ? N3 C6 1.330(8) . ? N3 C8 1.347(7) . ? C3 C4 1.507(7) . ? C3 C5 1.526(8) . ? C3 H3 1.0000 . ? O4 H4A 0.9300 . ? O4 H4B 0.8769 . ? N4 C11 1.310(9) 2_675 ? N4 C11 1.310(9) . ? O5 H5E 0.9733 . ? O5 H5D 0.9626 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? O6 H6B 0.8832 . ? O6 H6A 0.8879 . ? C6 C7 1.377(7) . ? C6 H6 0.9500 . ? C7 C10 1.381(8) . ? C7 H7 0.9500 . ? C8 C9 1.358(8) . ? C8 H8 0.9500 . ? C9 C10 1.408(8) . ? C9 H9 0.9500 . ? C10 C10 1.479(9) 3_576 ? C11 C12 1.381(9) . ? C11 H11 0.9500 . ? C12 C13 1.404(8) . ? C12 H12 0.9500 . ? C13 C12 1.404(8) 2_675 ? C13 C13 1.456(16) 3_576 ? 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 N2 Cu1 O2 82.76(18) . . ? N2 Cu1 N3 174.23(19) . . ? O2 Cu1 N3 95.60(17) . . ? N2 Cu1 N1 83.20(19) . . ? O2 Cu1 N1 161.22(19) . . ? N3 Cu1 N1 97.13(19) . . ? N2 Cu1 O4 94.97(18) . . ? O2 Cu1 O4 97.54(19) . . ? N3 Cu1 O4 90.73(17) . . ? N1 Cu1 O4 96.0(2) . . ? C1 N1 Cu1 108.7(4) . . ? C1 N1 H1A 110.0 . . ? Cu1 N1 H1A 110.0 . . ? C1 N1 H1B 110.0 . . ? Cu1 N1 H1B 110.0 . . ? H1A N1 H1B 108.3 . . ? N1 C1 C2 110.7(5) . . ? N1 C1 H1C 109.5 . . ? C2 C1 H1C 109.5 . . ? N1 C1 H1D 109.5 . . ? C2 C1 H1D 109.5 . . ? H1C C1 H1D 108.1 . . ? C4 O2 Cu1 114.8(3) . . ? C2 N2 C3 123.7(4) . . ? C2 N2 Cu1 120.2(4) . . ? C3 N2 Cu1 115.9(3) . . ? O1 C2 N2 127.3(6) . . ? O1 C2 C1 118.9(5) . . ? N2 C2 C1 113.8(5) . . ? C6 N3 C8 116.8(5) . . ? C6 N3 Cu1 120.8(4) . . ? C8 N3 Cu1 122.4(4) . . ? N2 C3 C4 108.6(4) . . ? N2 C3 C5 113.4(5) . . ? C4 C3 C5 109.4(5) . . ? N2 C3 H3 108.4 . . ? C4 C3 H3 108.4 . . ? C5 C3 H3 108.4 . . ? Cu1 O4 H4A 117.9 . . ? Cu1 O4 H4B 95.1 . . ? H4A O4 H4B 102.6 . . ? C11 N4 C11 113.3(9) 2_675 . ? O3 C4 O2 121.6(5) . . ? O3 C4 C3 121.5(5) . . ? O2 C4 C3 116.8(5) . . ? H5E O5 H5D 96.9 . . ? C3 C5 H5A 109.5 . . ? C3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? H6B O6 H6A 104.3 . . ? N3 C6 C7 123.5(6) . . ? N3 C6 H6 118.2 . . ? C7 C6 H6 118.2 . . ? C6 C7 C10 119.8(6) . . ? C6 C7 H7 120.1 . . ? C10 C7 H7 120.1 . . ? N3 C8 C9 123.4(6) . . ? N3 C8 H8 118.3 . . ? C9 C8 H8 118.3 . . ? C8 C9 C10 119.7(6) . . ? C8 C9 H9 120.1 . . ? C10 C9 H9 120.1 . . ? C7 C10 C9 116.6(5) . . ? C7 C10 C10 122.2(7) . 3_576 ? C9 C10 C10 121.2(7) . 3_576 ? N4 C11 C12 127.2(8) . . ? N4 C11 H11 116.4 . . ? C12 C11 H11 116.4 . . ? C11 C12 C13 118.3(8) . . ? C11 C12 H12 120.9 . . ? C13 C12 H12 120.9 . . ? C12 C13 C12 115.6(8) 2_675 . ? C12 C13 C13 122.2(4) 2_675 3_576 ? C12 C13 C13 122.2(4) . 3_576 ? 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 O6 H6B O1 0.88 1.81 2.693(15) 176.5 . O5 H5D O1 0.96 2.05 2.788(14) 131.9 . N1 H1B N4 0.92 2.39 3.266(7) 158.0 . N1 H1A O3 0.92 2.23 2.948(7) 134.4 2_575 O4 H4B O3 0.88 1.94 2.766(6) 156.4 7_565 O4 H4A O6 0.93 1.95 2.762(14) 144.0 8_545 O5 H5E O2 0.97 1.99 2.937(15) 163.8 7_565 O6 H6A O5 0.89 2.38 3.152(19) 145.0 2_675 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.509 _refine_diff_density_min -0.512 _refine_diff_density_rms 0.082 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material 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 _platon_squeeze_void_content 1 -0.014 0.000 0.000 539 60 ' ' 2 -0.029 0.500 0.500 539 60 ' ' _platon_squeeze_details ; ; # Attachment '- complex 2.cif' data_II _database_code_depnum_ccdc_archive 'CCDC 838897' #TrackingRef '- complex 2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H28 Cu2 N6 O8, 8(H2 O)' _chemical_formula_sum 'C20 H44 Cu2 N6 O16' _chemical_formula_weight 751.69 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 _symmetry_space_group_name_Hall -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.261 _cell_length_b 10.749 _cell_length_c 11.075 _cell_angle_alpha 68.967(7) _cell_angle_beta 77.087(8) _cell_angle_gamma 76.293(8) _cell_volume 774.6 _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2136 _cell_measurement_theta_min 2.3594 _cell_measurement_theta_max 27.5050 _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.611 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 1.453 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8752 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'RIGAKU/MSC(2004), CrystalClear Version 1.3.6' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ccd _diffrn_measurement_method CCD_Profile_fitting _diffrn_detector_area_resol_mean 14.6306 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8399 _diffrn_reflns_av_R_equivalents 0.0179 _diffrn_reflns_av_sigmaI/netI 0.0233 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3529 _reflns_number_gt 3256 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0572P)^2^+0.5049P] 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 3529 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0406 _refine_ls_R_factor_gt 0.0372 _refine_ls_wR_factor_ref 0.1057 _refine_ls_wR_factor_gt 0.1025 _refine_ls_goodness_of_fit_ref 1.094 _refine_ls_restrained_S_all 1.094 _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 0.37213(4) 0.67172(3) 0.23553(3) 0.02898(11) Uani 1 1 d . . . O1 O 0.3841(3) 0.48968(18) 0.22463(19) 0.0391(4) Uani 1 1 d . . . O2 O 0.2548(3) 0.37627(19) 0.1436(2) 0.0483(5) Uani 1 1 d . . . O3 O -0.1269(2) 0.85578(19) 0.1041(2) 0.0420(4) Uani 1 1 d . . . O4 O 0.6107(3) 0.74851(19) 0.04667(18) 0.0396(4) Uani 1 1 d . . . H4A H 0.6614 0.6980 -0.0041 0.048 Uiso 1 1 d R . . H4B H 0.7156 0.7699 0.0546 0.048 Uiso 1 1 d R . . N1 N 0.2669(3) 0.8560(2) 0.2590(2) 0.0338(4) Uani 1 1 d . . . H1A H 0.2476 0.8474 0.3464 0.041 Uiso 1 1 calc R . . H1B H 0.3539 0.9134 0.2155 0.041 Uiso 1 1 calc R . . N2 N 0.1592(3) 0.7151(2) 0.14576(19) 0.0291(4) Uani 1 1 d . . . N3 N 0.5871(3) 0.6094(2) 0.34193(19) 0.0308(4) Uani 1 1 d . . . C1 C 0.2655(3) 0.4824(2) 0.1591(2) 0.0329(5) Uani 1 1 d . . . C2 C 0.1320(3) 0.6128(2) 0.0969(2) 0.0308(5) Uani 1 1 d . . . H2 H -0.0038 0.5976 0.1259 0.037 Uiso 1 1 calc R . . C3 C 0.1760(5) 0.6533(3) -0.0514(3) 0.0464(6) Uani 1 1 d . . . H3A H 0.0946 0.7396 -0.0898 0.070 Uiso 1 1 calc R . . H3B H 0.1506 0.5834 -0.0799 0.070 Uiso 1 1 calc R . . H3C H 0.3112 0.6630 -0.0801 0.070 Uiso 1 1 calc R . . C4 C 0.0306(3) 0.8227(2) 0.1465(2) 0.0300(5) Uani 1 1 d . . . C5 C 0.0830(4) 0.9133(3) 0.2067(3) 0.0384(6) Uani 1 1 d . . . H5A H 0.0929 1.0028 0.1396 0.046 Uiso 1 1 calc R . . H5B H -0.0204 0.9267 0.2784 0.046 Uiso 1 1 calc R . . C6 C 0.6978(4) 0.4881(3) 0.3517(3) 0.0393(6) Uani 1 1 d . . . H6 H 0.6632 0.4306 0.3154 0.047 Uiso 1 1 calc R . . C7 C 0.8589(4) 0.4428(3) 0.4117(3) 0.0402(6) Uani 1 1 d . . . H7 H 0.9335 0.3565 0.4149 0.048 Uiso 1 1 calc R . . C8 C 0.6382(4) 0.6866(3) 0.3968(3) 0.0422(6) Uani 1 1 d . . . H8 H 0.5616 0.7727 0.3919 0.051 Uiso 1 1 calc R . . C9 C 0.7971(4) 0.6470(3) 0.4601(3) 0.0414(6) Uani 1 1 d . . . H9 H 0.8266 0.7049 0.4982 0.050 Uiso 1 1 calc R . . C10 C 0.9129(3) 0.5227(2) 0.4675(2) 0.0295(5) Uani 1 1 d . . . O5 O 0.4405(3) 0.9652(2) 0.8475(2) 0.0540(5) Uani 1 1 d . . . O7 O 0.2325(8) 0.8936(5) 0.5169(4) 0.1376(17) Uani 1 1 d . . . O6 O 0.4999(8) 0.8308(4) 0.6655(3) 0.152(2) Uani 1 1 d . . . O8 O -0.1070(8) 0.8474(5) 0.6490(6) 0.168(2) Uani 1 1 d . . . H5C H 0.4754 0.9026 0.9224 0.201 Uiso 1 1 d R . . H5D H 0.3360 1.0232 0.8694 0.201 Uiso 1 1 d R . . H7B H 0.2222 0.9782 0.4601 0.201 Uiso 1 1 d R . . H7A H 0.3153 0.8910 0.5698 0.201 Uiso 1 1 d R . . H6A H 0.4810 0.8740 0.7252 0.201 Uiso 1 1 d R . . H6B H 0.5265 0.7400 0.7169 0.201 Uiso 1 1 d R . . H8A H -0.0011 0.8535 0.5884 0.201 Uiso 1 1 d R . . H8B H -0.1792 0.7755 0.6752 0.201 Uiso 1 1 d 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 0.02615(17) 0.03099(17) 0.03525(17) -0.01475(12) -0.01451(11) 0.00054(11) O1 0.0391(9) 0.0327(9) 0.0519(10) -0.0171(8) -0.0231(8) 0.0027(7) O2 0.0540(12) 0.0359(10) 0.0665(13) -0.0268(9) -0.0213(10) -0.0022(8) O3 0.0296(9) 0.0418(10) 0.0630(12) -0.0249(9) -0.0228(8) 0.0058(7) O4 0.0321(9) 0.0498(11) 0.0449(10) -0.0229(8) -0.0086(7) -0.0074(8) N1 0.0322(10) 0.0349(10) 0.0410(11) -0.0173(9) -0.0145(8) -0.0020(8) N2 0.0239(9) 0.0313(10) 0.0385(10) -0.0182(8) -0.0117(8) 0.0004(7) N3 0.0278(9) 0.0353(10) 0.0316(9) -0.0117(8) -0.0121(8) -0.0015(8) C1 0.0291(11) 0.0332(12) 0.0391(12) -0.0158(10) -0.0077(9) -0.0018(9) C2 0.0256(10) 0.0355(12) 0.0386(12) -0.0183(10) -0.0116(9) -0.0029(9) C3 0.0555(17) 0.0504(16) 0.0410(14) -0.0211(12) -0.0173(12) -0.0040(13) C4 0.0251(10) 0.0313(11) 0.0356(11) -0.0126(9) -0.0094(9) -0.0013(9) C5 0.0358(13) 0.0335(12) 0.0547(15) -0.0235(11) -0.0202(11) 0.0050(10) C6 0.0367(13) 0.0420(14) 0.0493(14) -0.0225(12) -0.0213(11) 0.0002(11) C7 0.0359(13) 0.0381(13) 0.0545(15) -0.0225(12) -0.0216(12) 0.0048(10) C8 0.0414(14) 0.0410(14) 0.0541(16) -0.0234(12) -0.0284(12) 0.0073(11) C9 0.0412(14) 0.0426(14) 0.0516(15) -0.0249(12) -0.0262(12) 0.0051(11) C10 0.0271(11) 0.0368(12) 0.0261(10) -0.0102(9) -0.0095(9) -0.0030(9) O5 0.0433(11) 0.0449(11) 0.0679(14) -0.0166(10) -0.0109(10) 0.0028(9) O7 0.207(5) 0.128(3) 0.080(2) -0.059(2) -0.015(3) -0.001(3) O6 0.257(6) 0.089(3) 0.069(2) -0.0212(19) -0.039(3) 0.053(3) O8 0.179(5) 0.103(3) 0.206(6) -0.052(4) 0.012(4) -0.032(3) _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 N2 1.8999(18) . ? Cu1 O1 1.9838(18) . ? Cu1 N3 2.0086(19) . ? Cu1 N1 2.035(2) . ? Cu1 O4 2.4239(19) . ? O1 C1 1.275(3) . ? O2 C1 1.235(3) . ? O3 C4 1.259(3) . ? O4 H4A 0.8819 . ? O4 H4B 0.8771 . ? N1 C5 1.482(3) . ? N1 H1A 0.9200 . ? N1 H1B 0.9200 . ? N2 C4 1.304(3) . ? N2 C2 1.455(3) . ? N3 C6 1.341(3) . ? N3 C8 1.343(3) . ? C1 C2 1.530(3) . ? C2 C3 1.519(4) . ? C2 H2 1.0000 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 C5 1.513(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.376(3) . ? C6 H6 0.9500 . ? C7 C10 1.386(3) . ? C7 H7 0.9500 . ? C8 C9 1.385(3) . ? C8 H8 0.9500 . ? C9 C10 1.385(3) . ? C9 H9 0.9500 . ? C10 C10 1.490(4) 2_766 ? O5 H5C 0.9041 . ? O5 H5D 0.9082 . ? O7 H7B 0.8980 . ? O7 H7A 0.9185 . ? O6 H6A 0.9059 . ? O6 H6B 0.9357 . ? O8 H8A 0.8988 . ? O8 H8B 0.9588 . ? 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 N2 Cu1 O1 82.36(7) . . ? N2 Cu1 N3 174.37(8) . . ? O1 Cu1 N3 93.61(8) . . ? N2 Cu1 N1 83.27(8) . . ? O1 Cu1 N1 161.23(8) . . ? N3 Cu1 N1 99.80(8) . . ? N2 Cu1 O4 97.89(7) . . ? O1 Cu1 O4 97.81(7) . . ? N3 Cu1 O4 86.53(7) . . ? N1 Cu1 O4 96.07(8) . . ? C1 O1 Cu1 115.43(15) . . ? Cu1 O4 H4A 119.9 . . ? Cu1 O4 H4B 121.2 . . ? H4A O4 H4B 99.2 . . ? C5 N1 Cu1 109.70(14) . . ? C5 N1 H1A 109.7 . . ? Cu1 N1 H1A 109.7 . . ? C5 N1 H1B 109.7 . . ? Cu1 N1 H1B 109.7 . . ? H1A N1 H1B 108.2 . . ? C4 N2 C2 122.48(19) . . ? C4 N2 Cu1 120.01(16) . . ? C2 N2 Cu1 116.74(14) . . ? C6 N3 C8 116.7(2) . . ? C6 N3 Cu1 119.26(16) . . ? C8 N3 Cu1 123.81(17) . . ? O2 C1 O1 123.2(2) . . ? O2 C1 C2 119.3(2) . . ? O1 C1 C2 117.5(2) . . ? N2 C2 C3 112.4(2) . . ? N2 C2 C1 106.80(18) . . ? C3 C2 C1 110.4(2) . . ? N2 C2 H2 109.1 . . ? C3 C2 H2 109.1 . . ? C1 C2 H2 109.1 . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? O3 C4 N2 126.8(2) . . ? O3 C4 C5 119.0(2) . . ? N2 C4 C5 114.14(19) . . ? N1 C5 C4 112.30(19) . . ? N1 C5 H5A 109.1 . . ? C4 C5 H5A 109.1 . . ? N1 C5 H5B 109.1 . . ? C4 C5 H5B 109.1 . . ? H5A C5 H5B 107.9 . . ? N3 C6 C7 123.2(2) . . ? N3 C6 H6 118.4 . . ? C7 C6 H6 118.4 . . ? C6 C7 C10 120.3(2) . . ? C6 C7 H7 119.9 . . ? C10 C7 H7 119.9 . . ? N3 C8 C9 123.3(2) . . ? N3 C8 H8 118.4 . . ? C9 C8 H8 118.4 . . ? C8 C9 C10 119.7(2) . . ? C8 C9 H9 120.2 . . ? C10 C9 H9 120.2 . . ? C9 C10 C7 116.9(2) . . ? C9 C10 C10 121.4(3) . 2_766 ? C7 C10 C10 121.7(3) . 2_766 ? H5C O5 H5D 107.9 . . ? H7B O7 H7A 104.5 . . ? H6A O6 H6B 102.0 . . ? H8A O8 H8B 123.5 . . ? 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 N1 H1A O7 0.92 2.09 2.974(4) 160.1 . O8 H8A O7 0.90 1.79 2.629(8) 155.1 . O7 H7A O6 0.92 1.75 2.635(7) 160.3 . O6 H6A O5 0.91 1.88 2.782(5) 179.4 . O4 H4B O3 0.88 1.90 2.734(2) 158.8 1_655 O4 H4A O2 0.88 1.91 2.772(3) 166.9 2_665 O5 H5C O4 0.90 1.95 2.826(3) 162.8 1_556 O5 H5D O3 0.91 1.80 2.700(3) 174.4 2_576 O6 H6B O1 0.94 2.28 3.183(4) 161.0 2_666 O7 H7B O8 0.90 1.94 2.799(7) 159.9 2_576 O8 H8B O2 0.96 2.14 2.892(6) 134.5 2_566 O8 H8B O6 0.96 2.28 2.863(9) 118.3 1_455 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.588 _refine_diff_density_min -0.556 _refine_diff_density_rms 0.072