# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Shu-Pao Wu' _publ_contact_author_email SPWU@MAIL.NCTU.EDU.TW loop_ _publ_author_name 'Shu-Pao Wu' 'Chih-Hao Lee' # Attachment 'L-pasp.cif' data_L-pasp _database_code_depnum_ccdc_archive 'CCDC 700823' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H20 Cu N2 O9' _chemical_formula_weight 375.82 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 P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.5157(3) _cell_length_b 10.8984(3) _cell_length_c 17.6615(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1639.12(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2770 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 25 _exptl_crystal_description Tabullar _exptl_crystal_colour Blue _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.523 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 780 _exptl_absorpt_coefficient_mu 1.376 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.76418 _exptl_absorpt_correction_T_max 0.95032 _exptl_absorpt_process_details ? _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 area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8932 _diffrn_reflns_av_R_equivalents 0.0370 _diffrn_reflns_av_sigmaI/netI 0.0562 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 28.31 _reflns_number_total 4071 _reflns_number_gt 3075 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEXII' _computing_cell_refinement 'Bruker APEXII' _computing_data_reduction 'Bruker Saint' _computing_structure_solution 'Shelxtl-97 (Sheldrick, 1990)' _computing_structure_refinement 'Shelxtl-97 (Sheldrick, 2000)' _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^)+(0.0920P)^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 SHELXL _refine_ls_extinction_coef 0.083(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.02(3) _refine_ls_number_reflns 4071 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0728 _refine_ls_R_factor_gt 0.0522 _refine_ls_wR_factor_ref 0.1657 _refine_ls_wR_factor_gt 0.1227 _refine_ls_goodness_of_fit_ref 1.103 _refine_ls_restrained_S_all 1.103 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _chemical_absolute_configuration rm 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 0.39330(6) 0.22959(5) 0.24939(3) 0.0327(2) Uani 1 1 d . . . O1 O 0.5732(4) 0.1856(3) 0.31630(19) 0.0410(8) Uani 1 1 d . . . O2 O 0.6254(5) 0.0815(4) 0.4210(2) 0.0515(10) Uani 1 1 d . . . O3 O 0.4978(4) -0.1360(3) 0.2986(2) 0.0414(8) Uani 1 1 d . . . O4 O 0.4453(5) -0.2660(4) 0.3926(2) 0.0585(11) Uani 1 1 d . . . OW1 O 0.2866(5) 0.3587(4) 0.3370(2) 0.0593(11) Uani 1 1 d . . . HW1A H 0.1808 0.3890 0.3308 0.071 Uiso 1 1 d . . . HW1B H 0.3483 0.3874 0.3792 0.071 Uiso 1 1 d . . . OW2 O -0.0563(6) 0.1073(5) 0.4525(3) 0.0736(14) Uani 1 1 d . . . HW2A H -0.1215 0.1296 0.4100 0.088 Uiso 1 1 d . . . HW2B H -0.1062 0.0841 0.4995 0.088 Uiso 1 1 d . . . OW3 O 0.5326(5) 0.1635(5) 0.5654(2) 0.0622(12) Uani 1 1 d . . . HW3A H 0.4371 0.2092 0.5718 0.075 Uiso 1 1 d . . . HW3B H 0.5936 0.1416 0.6096 0.075 Uiso 1 1 d . . . OW4 O 0.2307(5) -0.1127(4) 0.1624(3) 0.0596(12) Uani 1 1 d . . . HW4A H 0.1457 -0.0822 0.1316 0.072 Uiso 1 1 d . . . HW4B H 0.2503 -0.1998 0.1640 0.072 Uiso 1 1 d . . . OW5 O 0.5197(6) -0.5043(3) 0.4083(3) 0.0645(13) Uani 1 1 d . . . HW5A H 0.5784 -0.5437 0.3694 0.077 Uiso 1 1 d . . . HW5B H 0.4908 -0.5462 0.4535 0.077 Uiso 1 1 d . . . N1 N 0.1979(5) 0.2242(4) 0.1865(2) 0.0386(9) Uani 1 1 d . . . N2 N 0.3019(5) 0.0786(3) 0.2930(2) 0.0319(8) Uani 1 1 d . . . H2B H 0.3367 0.0137 0.2652 0.038 Uiso 1 1 calc R . . C1 C 0.1717(7) 0.2874(6) 0.1229(3) 0.0538(14) Uani 1 1 d . . . H1A H 0.2429 0.3469 0.1072 0.065 Uiso 1 1 calc R . . C2 C 0.0392(8) 0.2643(7) 0.0803(4) 0.0658(19) Uani 1 1 d . . . H2A H 0.0232 0.3052 0.0348 0.079 Uiso 1 1 calc R . . C3 C -0.0714(8) 0.1785(7) 0.1064(4) 0.0687(19) Uani 1 1 d . . . H3A H -0.1605 0.1610 0.0779 0.082 Uiso 1 1 calc R . . C4 C -0.0464(7) 0.1210(6) 0.1745(4) 0.0561(15) Uani 1 1 d . . . H4A H -0.1209 0.0675 0.1944 0.067 Uiso 1 1 calc R . . C5 C 0.0900(6) 0.1440(5) 0.2123(3) 0.0395(11) Uani 1 1 d . . . C6 C 0.1296(6) 0.0847(5) 0.2853(3) 0.0440(12) Uani 1 1 d . . . H6A H 0.0854 0.1316 0.3269 0.053 Uiso 1 1 calc R . . H6B H 0.0856 0.0026 0.2869 0.053 Uiso 1 1 calc R . . C7 C 0.3672(6) 0.0672(4) 0.3702(3) 0.0348(11) Uani 1 1 d . . . H7A H 0.3078 0.1238 0.4024 0.042 Uiso 1 1 calc R . . C8 C 0.5362(6) 0.1123(4) 0.3695(3) 0.0369(11) Uani 1 1 d . . . C9 C 0.3476(7) -0.0595(4) 0.4039(3) 0.0401(12) Uani 1 1 d . . . H9A H 0.2369 -0.0802 0.4038 0.048 Uiso 1 1 calc R . . H9B H 0.3823 -0.0574 0.4562 0.048 Uiso 1 1 calc R . . C10 C 0.4382(6) -0.1616(5) 0.3623(3) 0.0377(11) 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 0.0362(3) 0.0298(3) 0.0321(3) 0.0032(3) 0.0003(3) -0.0032(2) O1 0.0401(19) 0.0390(18) 0.0440(19) 0.0076(15) -0.0050(15) -0.0068(15) O2 0.056(2) 0.057(2) 0.042(2) 0.0037(17) -0.0125(19) -0.001(2) O3 0.052(2) 0.0353(18) 0.0367(18) 0.0003(14) 0.0068(16) 0.0060(17) O4 0.068(3) 0.037(2) 0.070(3) 0.0140(19) 0.018(2) 0.0117(19) OW1 0.059(3) 0.053(2) 0.066(3) -0.022(2) 0.011(2) 0.000(2) OW2 0.072(3) 0.090(4) 0.059(3) 0.014(2) -0.001(3) -0.016(3) OW3 0.061(3) 0.078(3) 0.047(2) -0.001(2) -0.003(2) 0.014(2) OW4 0.057(3) 0.041(2) 0.080(3) -0.004(2) -0.012(2) 0.0112(19) OW5 0.087(4) 0.036(2) 0.070(3) 0.0048(19) 0.018(2) -0.003(2) N1 0.038(2) 0.041(2) 0.037(2) 0.0034(18) -0.0019(17) 0.0020(19) N2 0.037(2) 0.0258(18) 0.033(2) 0.0004(15) 0.0018(17) 0.0000(16) C1 0.052(3) 0.057(4) 0.052(3) 0.012(3) -0.004(3) 0.013(3) C2 0.067(4) 0.084(5) 0.046(3) 0.006(3) -0.009(3) 0.029(4) C3 0.047(3) 0.075(5) 0.084(5) -0.022(4) -0.023(3) 0.014(3) C4 0.045(3) 0.053(4) 0.070(4) -0.005(3) -0.008(3) 0.007(3) C5 0.033(2) 0.037(3) 0.048(3) -0.008(2) 0.001(2) 0.000(2) C6 0.035(3) 0.044(3) 0.053(3) 0.005(2) 0.001(2) -0.007(2) C7 0.045(3) 0.027(2) 0.032(2) -0.0003(17) 0.008(2) 0.002(2) C8 0.045(3) 0.029(2) 0.036(2) -0.0038(19) -0.006(2) 0.002(2) C9 0.049(3) 0.035(3) 0.036(3) 0.007(2) 0.009(2) 0.004(2) C10 0.036(2) 0.033(3) 0.044(3) 0.000(2) 0.002(2) -0.0022(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O3 1.930(3) 3_655 ? Cu1 N2 1.977(4) . ? Cu1 O1 1.994(3) . ? Cu1 N1 2.001(4) . ? Cu1 OW1 2.280(4) . ? O1 C8 1.272(6) . ? O2 C8 1.232(6) . ? O3 C10 1.265(6) . ? O3 Cu1 1.930(3) 3_645 ? O4 C10 1.259(6) . ? OW1 HW1A 0.9655 . ? OW1 HW1B 0.9646 . ? OW2 HW2A 0.9652 . ? OW2 HW2B 0.9660 . ? OW3 HW3A 0.9603 . ? OW3 HW3B 0.9673 . ? OW4 HW4A 0.9648 . ? OW4 HW4B 0.9643 . ? OW5 HW5A 0.9515 . ? OW5 HW5B 0.9529 . ? N1 C1 1.337(7) . ? N1 C5 1.348(6) . ? N2 C6 1.476(6) . ? N2 C7 1.478(6) . ? N2 H2B 0.9100 . ? C1 C2 1.378(9) . ? C1 H1A 0.9300 . ? C2 C3 1.405(11) . ? C2 H2A 0.9300 . ? C3 C4 1.373(10) . ? C3 H3A 0.9300 . ? C4 C5 1.363(8) . ? C4 H4A 0.9300 . ? C5 C6 1.481(8) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C9 1.513(6) . ? C7 C8 1.521(7) . ? C7 H7A 0.9800 . ? C9 C10 1.540(7) . ? C9 H9A 0.9700 . ? C9 H9B 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 O3 Cu1 N2 172.89(16) 3_655 . ? O3 Cu1 O1 94.24(15) 3_655 . ? N2 Cu1 O1 82.60(15) . . ? O3 Cu1 N1 100.25(16) 3_655 . ? N2 Cu1 N1 82.21(16) . . ? O1 Cu1 N1 163.92(17) . . ? O3 Cu1 OW1 91.19(16) 3_655 . ? N2 Cu1 OW1 95.33(16) . . ? O1 Cu1 OW1 93.01(17) . . ? N1 Cu1 OW1 93.61(16) . . ? C8 O1 Cu1 113.5(3) . . ? C10 O3 Cu1 114.6(3) . 3_645 ? Cu1 OW1 HW1A 120.4 . . ? Cu1 OW1 HW1B 120.5 . . ? HW1A OW1 HW1B 119.0 . . ? HW2A OW2 HW2B 118.8 . . ? HW3A OW3 HW3B 119.2 . . ? HW4A OW4 HW4B 119.1 . . ? HW5A OW5 HW5B 121.6 . . ? C1 N1 C5 120.3(5) . . ? C1 N1 Cu1 126.2(4) . . ? C5 N1 Cu1 113.5(3) . . ? C6 N2 C7 117.5(4) . . ? C6 N2 Cu1 108.6(3) . . ? C7 N2 Cu1 106.3(3) . . ? C6 N2 H2B 108.0 . . ? C7 N2 H2B 108.0 . . ? Cu1 N2 H2B 108.0 . . ? N1 C1 C2 120.1(6) . . ? N1 C1 H1A 120.0 . . ? C2 C1 H1A 120.0 . . ? C1 C2 C3 119.4(6) . . ? C1 C2 H2A 120.3 . . ? C3 C2 H2A 120.3 . . ? C4 C3 C2 119.2(6) . . ? C4 C3 H3A 120.4 . . ? C2 C3 H3A 120.4 . . ? C5 C4 C3 118.5(6) . . ? C5 C4 H4A 120.7 . . ? C3 C4 H4A 120.7 . . ? N1 C5 C4 122.3(5) . . ? N1 C5 C6 115.0(4) . . ? C4 C5 C6 122.7(5) . . ? N2 C6 C5 109.0(4) . . ? N2 C6 H6A 109.9 . . ? C5 C6 H6A 109.9 . . ? N2 C6 H6B 109.9 . . ? C5 C6 H6B 109.9 . . ? H6A C6 H6B 108.3 . . ? N2 C7 C9 113.4(4) . . ? N2 C7 C8 108.7(4) . . ? C9 C7 C8 113.7(4) . . ? N2 C7 H7A 106.8 . . ? C9 C7 H7A 106.8 . . ? C8 C7 H7A 106.8 . . ? O2 C8 O1 124.3(5) . . ? O2 C8 C7 119.3(5) . . ? O1 C8 C7 116.3(4) . . ? C7 C9 C10 114.6(4) . . ? C7 C9 H9A 108.6 . . ? C10 C9 H9A 108.6 . . ? C7 C9 H9B 108.6 . . ? C10 C9 H9B 108.6 . . ? H9A C9 H9B 107.6 . . ? O4 C10 O3 123.9(5) . . ? O4 C10 C9 118.3(4) . . ? O3 C10 C9 117.7(4) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.151 _refine_diff_density_min -1.182 _refine_diff_density_rms 0.425 data_D-pasp _database_code_depnum_ccdc_archive 'CCDC 700824' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H20 Cu N2 O9' _chemical_formula_sum 'C10 H20 Cu N2 O9' _chemical_formula_weight 375.82 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 P2(1)2(1)2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/2, y+1/2, -z' 'x+1/2, -y+1/2, -z' _cell_length_a 11.2411(3) _cell_length_b 16.5043(5) _cell_length_c 8.4442(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1566.62(8) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4500 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 25 _exptl_crystal_description Tabullar _exptl_crystal_colour Blue _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.593 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 780 _exptl_absorpt_coefficient_mu 1.440 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.85700 _exptl_absorpt_correction_T_max 0.94955 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8270 _diffrn_reflns_av_R_equivalents 0.0413 _diffrn_reflns_av_sigmaI/netI 0.0536 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 4 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 28.28 _reflns_number_total 3743 _reflns_number_gt 2909 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEXII' _computing_cell_refinement 'Bruker APEXII' _computing_data_reduction 'Bruker Saint' _computing_structure_solution 'Shelxtl-97 (Sheldrick, 1990)' _computing_structure_refinement 'Shelxtl-97 (Sheldrick, 2000)' _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^)+(0.0856P)^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 0.00(3) _refine_ls_number_reflns 3743 _refine_ls_number_parameters 195 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0549 _refine_ls_R_factor_gt 0.0361 _refine_ls_wR_factor_ref 0.1494 _refine_ls_wR_factor_gt 0.0968 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.078 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _chemical_absolute_configuration rm 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 -0.09552(4) 0.74923(3) 0.60830(6) 0.03003(16) Uani 1 1 d . . . O1 O -0.0548(3) 0.6992(2) 0.4036(4) 0.0407(8) Uani 1 1 d . . . O2 O 0.0613(4) 0.6038(3) 0.3009(6) 0.0675(13) Uani 1 1 d . . . O3 O 0.2697(3) 0.69395(19) 0.4825(4) 0.0383(8) Uani 1 1 d . . . O4 O 0.3782(3) 0.5815(2) 0.5001(5) 0.0488(10) Uani 1 1 d . . . OW1 O -0.2144(3) 0.6455(2) 0.6819(5) 0.0509(9) Uani 1 1 d . . . HW1A H -0.2405 0.6397 0.7904 0.061 Uiso 1 1 d . . . HW1B H -0.2407 0.6055 0.6052 0.061 Uiso 1 1 d . . . OW2 O 0.6169(3) 0.5841(2) 0.4702(5) 0.0525(10) Uani 1 1 d . . . HW2A H 0.6674 0.6178 0.5334 0.063 Uiso 1 1 d . . . HW2B H 0.6511 0.5480 0.3930 0.063 Uiso 1 1 d . . . OW3 O 0.0000 0.5000 0.0721(6) 0.0600(15) Uani 1 2 d S . . HW3A H -0.0807 0.4815 0.0628 0.072 Uiso 0.50 1 d P . . HW3B H 0.0587 0.4812 -0.0029 0.072 Uiso 0.50 1 d P . . OW4 O 0.7824(4) 0.5725(3) 0.9711(5) 0.0707(13) Uani 1 1 d . . . HW4A H 0.8359 0.5748 0.8816 0.085 Uiso 1 1 d . . . HW4B H 0.8151 0.5646 1.0755 0.085 Uiso 1 1 d . . . OW5 O 0.7339(3) 0.6701(2) 0.2328(5) 0.0582(11) Uani 1 1 d . . . HW5A H 0.7589 0.6170 0.1961 0.070 Uiso 1 1 d . . . HW5B H 0.7869 0.7154 0.2171 0.070 Uiso 1 1 d . . . N1 N -0.0845(3) 0.7996(2) 0.8248(5) 0.0383(9) Uani 1 1 d . . . N2 N 0.0552(3) 0.6957(2) 0.6773(5) 0.0310(8) Uani 1 1 d . . . H2A H 0.1176 0.7280 0.6505 0.037 Uiso 1 1 calc R . . C1 C -0.1380(5) 0.8664(4) 0.8786(7) 0.0522(14) Uani 1 1 d . . . H1 H -0.1929 0.8925 0.8137 0.063 Uiso 1 1 calc R . . C2 C -0.1151(6) 0.8983(4) 1.0265(8) 0.0655(18) Uani 1 1 d . . . H2 H -0.1535 0.9450 1.0610 0.079 Uiso 1 1 calc R . . C3 C -0.0344(6) 0.8594(5) 1.1213(8) 0.074(2) Uani 1 1 d . . . H3 H -0.0171 0.8795 1.2216 0.089 Uiso 1 1 calc R . . C4 C 0.0206(5) 0.7906(5) 1.0670(7) 0.0611(16) Uani 1 1 d . . . H4 H 0.0752 0.7636 1.1307 0.073 Uiso 1 1 calc R . . C5 C -0.0051(4) 0.7618(3) 0.9193(5) 0.0410(11) Uani 1 1 d . . . C6 C 0.0520(4) 0.6871(3) 0.8510(6) 0.0424(12) Uani 1 1 d . . . H6A H 0.1321 0.6810 0.8920 0.051 Uiso 1 1 calc R . . H6B H 0.0065 0.6394 0.8801 0.051 Uiso 1 1 calc R . . C7 C 0.0615(4) 0.6207(3) 0.5835(6) 0.0362(11) Uani 1 1 d . . . H7 H 0.0011 0.5840 0.6264 0.043 Uiso 1 1 calc R . . C8 C 0.0220(4) 0.6424(3) 0.4132(6) 0.0423(12) Uani 1 1 d . . . C9 C 0.1801(4) 0.5754(3) 0.5907(8) 0.0461(14) Uani 1 1 d . . . H9A H 0.1989 0.5646 0.7008 0.055 Uiso 1 1 calc R . . H9B H 0.1707 0.5236 0.5379 0.055 Uiso 1 1 calc R . . C10 C 0.2833(4) 0.6191(3) 0.5172(6) 0.0344(10) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0222(2) 0.0291(3) 0.0388(3) 0.0004(3) -0.00156(18) 0.0027(2) O1 0.0337(16) 0.0455(19) 0.0429(19) -0.0071(17) -0.0002(14) 0.0068(15) O2 0.055(2) 0.071(3) 0.076(3) -0.038(3) -0.001(2) 0.011(2) O3 0.0277(15) 0.0308(17) 0.056(2) 0.0012(15) 0.0059(15) -0.0021(13) O4 0.0253(16) 0.045(2) 0.076(3) 0.0040(19) 0.0067(16) 0.0092(14) OW1 0.045(2) 0.053(2) 0.054(2) 0.0100(19) -0.0041(18) -0.0177(17) OW2 0.0292(18) 0.049(2) 0.079(3) -0.004(2) -0.0064(18) -0.0016(15) OW3 0.079(4) 0.063(4) 0.038(3) 0.000 0.000 -0.011(3) OW4 0.077(3) 0.088(3) 0.048(2) 0.009(2) -0.001(2) -0.013(2) OW5 0.045(2) 0.061(3) 0.068(3) -0.004(2) -0.014(2) 0.0049(18) N1 0.0285(19) 0.044(2) 0.043(2) -0.0034(19) 0.0040(17) 0.0014(17) N2 0.0219(16) 0.0285(18) 0.043(2) 0.0041(17) 0.0026(15) -0.0023(14) C1 0.045(3) 0.059(3) 0.052(3) -0.009(3) 0.003(2) 0.009(2) C2 0.066(4) 0.074(4) 0.057(4) -0.021(3) 0.019(3) 0.002(3) C3 0.068(4) 0.114(6) 0.041(3) -0.020(4) 0.007(3) 0.004(4) C4 0.051(3) 0.094(5) 0.038(3) 0.001(3) 0.001(3) 0.001(3) C5 0.032(2) 0.055(3) 0.036(2) 0.008(2) 0.0034(17) -0.005(2) C6 0.035(2) 0.047(3) 0.045(3) 0.012(2) -0.004(2) 0.004(2) C7 0.0200(19) 0.024(2) 0.064(3) 0.004(2) 0.005(2) -0.0003(16) C8 0.027(2) 0.043(3) 0.057(3) -0.015(3) 0.001(2) -0.0026(19) C9 0.024(2) 0.029(2) 0.086(4) 0.012(3) 0.014(3) 0.0013(17) C10 0.024(2) 0.032(2) 0.048(3) 0.002(2) 0.002(2) -0.0012(17) _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 O3 1.940(3) 4_466 ? Cu1 O1 1.969(4) . ? Cu1 N2 1.998(3) . ? Cu1 N1 2.012(4) . ? Cu1 OW1 2.259(3) . ? O1 C8 1.278(6) . ? O2 C8 1.225(6) . ? O3 C10 1.278(5) . ? O3 Cu1 1.940(3) 4_566 ? O4 C10 1.243(5) . ? OW1 HW1A 0.9670 . ? OW1 HW1B 0.9703 . ? OW2 HW2A 0.9571 . ? OW2 HW2B 0.9638 . ? OW3 HW3A 0.9606 . ? OW3 HW3B 0.9653 . ? OW4 HW4A 0.9665 . ? OW4 HW4B 0.9645 . ? OW5 HW5A 0.9711 . ? OW5 HW5B 0.9644 . ? N1 C1 1.337(7) . ? N1 C5 1.350(6) . ? N2 C7 1.470(6) . ? N2 C6 1.474(6) . ? N2 H2A 0.9100 . ? C1 C2 1.379(9) . ? C1 H1 0.9300 . ? C2 C3 1.370(10) . ? C2 H2 0.9300 . ? C3 C4 1.372(10) . ? C3 H3 0.9300 . ? C4 C5 1.365(7) . ? C4 H4 0.9300 . ? C5 C6 1.505(7) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C9 1.530(6) . ? C7 C8 1.547(7) . ? C7 H7 0.9800 . ? C9 C10 1.500(6) . ? C9 H9A 0.9700 . ? C9 H9B 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 O3 Cu1 O1 92.13(14) 4_466 . ? O3 Cu1 N2 172.54(15) 4_466 . ? O1 Cu1 N2 82.72(15) . . ? O3 Cu1 N1 101.99(15) 4_466 . ? O1 Cu1 N1 163.01(15) . . ? N2 Cu1 N1 82.29(16) . . ? O3 Cu1 OW1 90.75(13) 4_466 . ? O1 Cu1 OW1 93.50(15) . . ? N2 Cu1 OW1 94.93(14) . . ? N1 Cu1 OW1 95.71(15) . . ? C8 O1 Cu1 114.2(3) . . ? C10 O3 Cu1 117.6(3) . 4_566 ? Cu1 OW1 HW1A 121.0 . . ? Cu1 OW1 HW1B 120.8 . . ? HW1A OW1 HW1B 118.3 . . ? HW2A OW2 HW2B 119.9 . . ? HW3A OW3 HW3B 119.4 . . ? HW4A OW4 HW4B 118.9 . . ? HW5A OW5 HW5B 118.4 . . ? C1 N1 C5 118.6(5) . . ? C1 N1 Cu1 128.5(4) . . ? C5 N1 Cu1 112.8(3) . . ? C7 N2 C6 117.1(4) . . ? C7 N2 Cu1 104.9(3) . . ? C6 N2 Cu1 108.2(3) . . ? C7 N2 H2A 108.8 . . ? C6 N2 H2A 108.8 . . ? Cu1 N2 H2A 108.8 . . ? N1 C1 C2 122.6(6) . . ? N1 C1 H1 118.7 . . ? C2 C1 H1 118.7 . . ? C3 C2 C1 118.3(6) . . ? C3 C2 H2 120.8 . . ? C1 C2 H2 120.8 . . ? C2 C3 C4 119.4(6) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C5 C4 C3 119.8(6) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? N1 C5 C4 121.3(5) . . ? N1 C5 C6 115.7(4) . . ? C4 C5 C6 123.0(5) . . ? N2 C6 C5 108.2(4) . . ? N2 C6 H6A 110.0 . . ? C5 C6 H6A 110.0 . . ? N2 C6 H6B 110.0 . . ? C5 C6 H6B 110.0 . . ? H6A C6 H6B 108.4 . . ? N2 C7 C9 115.6(4) . . ? N2 C7 C8 107.0(4) . . ? C9 C7 C8 113.6(4) . . ? N2 C7 H7 106.7 . . ? C9 C7 H7 106.7 . . ? C8 C7 H7 106.7 . . ? O2 C8 O1 125.2(5) . . ? O2 C8 C7 119.8(5) . . ? O1 C8 C7 115.0(4) . . ? C10 C9 C7 115.0(4) . . ? C10 C9 H9A 108.5 . . ? C7 C9 H9A 108.5 . . ? C10 C9 H9B 108.5 . . ? C7 C9 H9B 108.5 . . ? H9A C9 H9B 107.5 . . ? O4 C10 O3 124.0(4) . . ? O4 C10 C9 118.1(4) . . ? O3 C10 C9 117.8(4) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.951 _refine_diff_density_min -1.047 _refine_diff_density_rms 0.407