# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Chuan-De Wu' _publ_contact_author_email cdwu@zju.edu.cn _publ_author_name 'Chuan-De Wu' data_New1 _database_code_depnum_ccdc_archive 'CCDC 808136' #TrackingRef '- New1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H42 Cu2 N12 O23' _chemical_formula_weight 1233.98 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 17.7000(19) _cell_length_b 18.053(2) _cell_length_c 8.6682(9) _cell_angle_alpha 90.00 _cell_angle_beta 103.843(11) _cell_angle_gamma 90.00 _cell_volume 2689.4(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 11266 _cell_measurement_theta_min 2.67 _cell_measurement_theta_max 26.37 _exptl_crystal_description bloc _exptl_crystal_colour blue _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.524 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1264 _exptl_absorpt_coefficient_mu 0.883 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.871 _exptl_absorpt_correction_T_max 0.907 _exptl_absorpt_process_details CrysAlisPro _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 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3592 _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% ? _diffrn_reflns_number 11266 _diffrn_reflns_av_R_equivalents 0.0409 _diffrn_reflns_av_sigmaI/netI 0.0556 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.67 _diffrn_reflns_theta_max 26.37 _reflns_number_total 5151 _reflns_number_gt 3092 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro (Oxford Diffraction Ltd., 2010)' _computing_cell_refinement 'CrysAlisPro (Oxford Diffraction Ltd., 2010)' _computing_data_reduction 'CrysAlisPro (Oxford Diffraction Ltd., 2010)' _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^)+(0.0836P)^2^+1.6668P] 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 5151 _refine_ls_number_parameters 370 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1236 _refine_ls_R_factor_gt 0.0819 _refine_ls_wR_factor_ref 0.2243 _refine_ls_wR_factor_gt 0.1971 _refine_ls_goodness_of_fit_ref 1.167 _refine_ls_restrained_S_all 1.167 _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 0.48651(4) 0.95126(4) 0.60457(8) 0.0648(3) Uani 1 1 d . . . O1 O 0.4538(3) 1.1150(2) 0.4994(6) 0.0827(12) Uani 1 1 d . . . O2 O 0.4295(3) 1.0332(2) 0.6739(5) 0.0799(12) Uani 1 1 d . . . O3 O -0.3944(3) 1.4277(3) 0.0627(6) 0.0846(13) Uani 1 1 d . . . O4 O -0.4142(2) 1.5120(3) 0.2382(5) 0.0794(12) Uani 1 1 d . . . O5 O 0.4651(3) 0.8749(3) 0.7791(6) 0.0937(14) Uani 1 1 d . . . H5A H 0.4436 0.8289 0.7467 0.112 Uiso 1 1 calc R . . O6 O 0.1672(6) 0.8446(5) 0.5644(10) 0.157(3) Uani 1 1 d . . . O7 O 0.0706(6) 0.9175(10) 0.4148(13) 0.255(7) Uani 1 1 d . . . O8 O 0.1845(10) 0.9584(6) 0.5630(10) 0.234(6) Uani 1 1 d . . . O9 O 0.9454(4) 0.9328(4) 1.0204(9) 0.141(2) Uani 1 1 d . . . O10 O 0.8996(4) 0.8235(4) 0.9883(8) 0.124(2) Uani 1 1 d . . . O11 O 0.8958(4) 0.8858(5) 1.1934(8) 0.158(3) Uani 1 1 d . . . O101 O 0.3216(7) 0.8161(9) 0.7113(17) 0.154(6) Uani 0.50 1 d P . . N1 N 0.2390(3) 1.3156(3) 0.8083(6) 0.0721(13) Uani 1 1 d . . . N2 N 0.1447(3) 1.3693(3) 0.8786(6) 0.0797(15) Uani 1 1 d . . . N3 N 0.0061(3) 1.3615(4) 0.8067(6) 0.0784(15) Uani 1 1 d . . . N4 N -0.0962(3) 1.3674(3) 0.6159(6) 0.0795(15) Uani 1 1 d . . . N5 N 0.1364(9) 0.9080(8) 0.5101(14) 0.160(4) Uani 1 1 d . . . N6 N 0.9146(4) 0.8803(5) 1.0689(9) 0.0968(19) Uani 1 1 d . . . C1 C 0.4241(3) 1.0953(4) 0.6105(8) 0.0682(15) Uani 1 1 d . . . C2 C 0.3777(3) 1.1522(3) 0.6703(7) 0.0663(15) Uani 1 1 d . . . C3 C 0.3147(4) 1.1323(4) 0.7277(8) 0.0756(17) Uani 1 1 d . . . H3A H 0.3032 1.0824 0.7365 0.091 Uiso 1 1 calc R . . C4 C 0.2683(4) 1.1853(4) 0.7722(8) 0.0748(16) Uani 1 1 d . . . H4A H 0.2242 1.1715 0.8060 0.090 Uiso 1 1 calc R . . C5 C 0.2875(3) 1.2581(3) 0.7662(7) 0.0659(15) Uani 1 1 d . . . C6 C 0.3518(4) 1.2800(4) 0.7137(8) 0.0799(18) Uani 1 1 d . . . H6A H 0.3646 1.3299 0.7112 0.096 Uiso 1 1 calc R . . C7 C 0.3965(4) 1.2266(4) 0.6650(8) 0.0806(18) Uani 1 1 d . . . H7A H 0.4397 1.2405 0.6282 0.097 Uiso 1 1 calc R . . C8 C 0.1777(4) 1.3046(4) 0.8685(7) 0.0726(16) Uani 1 1 d . . . H8A H 0.1609 1.2592 0.8983 0.087 Uiso 1 1 calc R . . C9 C 0.2432(4) 1.3893(4) 0.7808(11) 0.097(2) Uani 1 1 d . . . H9A H 0.2807 1.4128 0.7391 0.116 Uiso 1 1 calc R . . C10 C 0.1842(5) 1.4222(5) 0.8241(12) 0.104(3) Uani 1 1 d . . . H10A H 0.1727 1.4725 0.8176 0.124 Uiso 1 1 calc R . . C11 C 0.0723(4) 1.3793(5) 0.9320(8) 0.095(2) Uani 1 1 d . . . H11A H 0.0732 1.3476 1.0228 0.114 Uiso 1 1 calc R . . H11B H 0.0685 1.4303 0.9648 0.114 Uiso 1 1 calc R . . C12 C -0.0437(4) 1.4073(4) 0.7161(8) 0.0780(18) Uani 1 1 d . . . H12A H -0.0421 1.4588 0.7218 0.094 Uiso 1 1 calc R . . C13 C -0.0158(4) 1.2901(5) 0.7589(9) 0.095(2) Uani 1 1 d . . . H13A H 0.0094 1.2471 0.8026 0.114 Uiso 1 1 calc R . . C14 C -0.0784(4) 1.2931(4) 0.6410(9) 0.089(2) Uani 1 1 d . . . H14A H -0.1053 1.2533 0.5857 0.107 Uiso 1 1 calc R . . C15 C -0.2526(4) 1.3888(4) 0.2557(8) 0.086(2) Uani 1 1 d . . . H15A H -0.2661 1.3699 0.1530 0.103 Uiso 1 1 calc R . . C16 C -0.1842(4) 1.3677(5) 0.3568(8) 0.093(2) Uani 1 1 d . . . H16A H -0.1511 1.3348 0.3230 0.112 Uiso 1 1 calc R . . C17 C -0.1650(4) 1.3950(4) 0.5060(8) 0.0805(18) Uani 1 1 d . . . C18 C -0.2119(4) 1.4465(4) 0.5584(8) 0.091(2) Uani 1 1 d . . . H18A H -0.1972 1.4666 0.6600 0.109 Uiso 1 1 calc R . . C19 C -0.2801(4) 1.4667(4) 0.4559(8) 0.0827(19) Uani 1 1 d . . . H19A H -0.3126 1.5006 0.4885 0.099 Uiso 1 1 calc R . . C20 C -0.3012(4) 1.4376(4) 0.3048(7) 0.0723(16) Uani 1 1 d . . . C21 C -0.3768(4) 1.4609(4) 0.1934(8) 0.0718(16) Uani 1 1 d . . . C22 C 0.4830(7) 0.8933(6) 0.9417(11) 0.141(4) Uani 1 1 d . . . H22A H 0.4694 0.8527 1.0013 0.212 Uiso 1 1 calc R . . H22B H 0.4542 0.9365 0.9575 0.212 Uiso 1 1 calc R . . H22C H 0.5378 0.9031 0.9773 0.212 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 0.0559(4) 0.0733(5) 0.0633(5) -0.0015(3) 0.0103(3) 0.0049(3) O1 0.086(3) 0.084(3) 0.085(3) 0.000(2) 0.032(3) 0.015(2) O2 0.084(3) 0.079(3) 0.083(3) 0.001(2) 0.031(2) 0.015(2) O3 0.068(3) 0.099(3) 0.078(3) -0.005(3) 0.000(2) 0.010(2) O4 0.062(2) 0.091(3) 0.078(3) -0.001(2) 0.004(2) 0.008(2) O5 0.112(4) 0.089(3) 0.085(3) 0.008(3) 0.030(3) -0.006(3) O6 0.214(9) 0.114(5) 0.154(6) 0.010(5) 0.063(6) -0.014(5) O7 0.132(7) 0.49(2) 0.140(7) -0.020(10) 0.024(6) -0.062(10) O8 0.404(18) 0.180(9) 0.120(6) -0.009(6) 0.065(9) -0.091(10) O9 0.163(6) 0.137(5) 0.139(6) 0.000(4) 0.068(5) -0.038(5) O10 0.152(6) 0.099(4) 0.110(4) 0.011(4) 0.010(4) 0.002(4) O11 0.149(6) 0.246(9) 0.085(4) -0.002(5) 0.037(4) -0.052(6) O101 0.089(8) 0.211(14) 0.148(10) 0.048(10) 0.001(7) -0.072(9) N1 0.063(3) 0.074(3) 0.075(3) -0.005(3) 0.008(3) 0.007(2) N2 0.068(3) 0.095(4) 0.072(3) -0.016(3) 0.008(3) 0.018(3) N3 0.067(3) 0.099(4) 0.068(3) -0.004(3) 0.013(3) 0.023(3) N4 0.064(3) 0.101(4) 0.070(3) 0.004(3) 0.009(3) 0.013(3) N5 0.209(13) 0.164(11) 0.133(9) -0.023(8) 0.095(9) -0.064(10) N6 0.088(4) 0.113(6) 0.086(5) 0.021(4) 0.015(4) -0.002(4) C1 0.060(3) 0.070(4) 0.072(4) -0.008(3) 0.011(3) 0.000(3) C2 0.061(3) 0.072(4) 0.064(3) 0.001(3) 0.010(3) 0.006(3) C3 0.077(4) 0.071(4) 0.082(4) 0.002(3) 0.024(3) 0.006(3) C4 0.070(4) 0.076(4) 0.083(4) -0.003(3) 0.028(3) 0.002(3) C5 0.062(3) 0.073(4) 0.058(3) -0.008(3) 0.006(3) 0.008(3) C6 0.087(4) 0.065(4) 0.093(5) -0.007(3) 0.030(4) -0.001(3) C7 0.070(4) 0.086(5) 0.092(4) -0.012(4) 0.031(4) -0.008(3) C8 0.061(4) 0.082(4) 0.072(4) -0.004(3) 0.009(3) 0.011(3) C9 0.083(5) 0.070(5) 0.138(7) -0.004(4) 0.028(5) -0.004(4) C10 0.081(5) 0.082(5) 0.148(8) -0.020(5) 0.029(5) 0.008(4) C11 0.078(4) 0.137(6) 0.064(4) -0.019(4) 0.006(4) 0.033(4) C12 0.065(4) 0.099(5) 0.068(4) -0.001(4) 0.012(3) 0.018(4) C13 0.073(4) 0.117(7) 0.091(5) 0.026(5) 0.011(4) 0.029(4) C14 0.074(4) 0.086(5) 0.104(5) 0.006(4) 0.017(4) 0.011(4) C15 0.074(4) 0.108(5) 0.071(4) -0.009(4) 0.009(3) 0.016(4) C16 0.078(4) 0.130(6) 0.070(4) -0.008(4) 0.013(4) 0.023(4) C17 0.056(3) 0.111(5) 0.072(4) 0.011(4) 0.009(3) 0.012(4) C18 0.081(5) 0.122(6) 0.063(4) -0.004(4) 0.005(4) 0.013(4) C19 0.072(4) 0.097(5) 0.072(4) 0.003(4) 0.002(3) 0.018(4) C20 0.059(3) 0.087(4) 0.068(4) 0.010(3) 0.009(3) 0.002(3) C21 0.060(4) 0.082(4) 0.071(4) 0.007(3) 0.011(3) -0.003(3) C22 0.164(10) 0.153(9) 0.111(7) 0.014(6) 0.040(7) 0.006(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 O3 1.953(4) 2_545 ? Cu1 O1 1.953(4) 3_676 ? Cu1 O2 1.965(4) . ? Cu1 O4 1.974(4) 4_686 ? Cu1 O5 2.146(5) . ? Cu1 Cu1 2.6506(15) 3_676 ? O1 C1 1.254(7) . ? O1 Cu1 1.953(4) 3_676 ? O2 C1 1.242(7) . ? O3 C21 1.253(8) . ? O3 Cu1 1.952(4) 2 ? O4 C21 1.251(8) . ? O4 Cu1 1.974(4) 4_485 ? O5 C22 1.409(10) . ? O5 H5A 0.9300 . ? O6 N5 1.306(14) . ? O7 N5 1.268(15) . ? O8 N5 1.255(12) . ? O9 N6 1.217(8) . ? O10 N6 1.233(9) . ? O11 N6 1.207(9) . ? N1 C8 1.326(8) . ? N1 C9 1.357(9) . ? N1 C5 1.448(7) . ? N2 C8 1.317(8) . ? N2 C10 1.335(10) . ? N2 C11 1.475(9) . ? N3 C12 1.322(8) . ? N3 C13 1.381(9) . ? N3 C11 1.430(8) . ? N4 C12 1.323(8) . ? N4 C14 1.383(9) . ? N4 C17 1.444(8) . ? C1 C2 1.483(8) . ? C2 C3 1.374(9) . ? C2 C7 1.387(9) . ? C3 C4 1.375(9) . ? C3 H3A 0.9300 . ? C4 C5 1.362(9) . ? C4 H4A 0.9300 . ? C5 C6 1.381(9) . ? C6 C7 1.376(9) . ? C6 H6A 0.9300 . ? C7 H7A 0.9300 . ? C8 H8A 0.9300 . ? C9 C10 1.330(10) . ? C9 H9A 0.9300 . ? C10 H10A 0.9300 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9300 . ? C13 C14 1.316(10) . ? C13 H13A 0.9300 . ? C14 H14A 0.9300 . ? C15 C16 1.368(9) . ? C15 C20 1.369(9) . ? C15 H15A 0.9300 . ? C16 C17 1.349(9) . ? C16 H16A 0.9300 . ? C17 C18 1.393(10) . ? C18 C19 1.366(9) . ? C18 H18A 0.9300 . ? C19 C20 1.377(9) . ? C19 H19A 0.9300 . ? C20 C21 1.509(9) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? 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 88.4(2) 2_545 3_676 ? O3 Cu1 O2 89.6(2) 2_545 . ? O1 Cu1 O2 167.59(19) 3_676 . ? O3 Cu1 O4 167.8(2) 2_545 4_686 ? O1 Cu1 O4 88.46(19) 3_676 4_686 ? O2 Cu1 O4 91.0(2) . 4_686 ? O3 Cu1 O5 97.3(2) 2_545 . ? O1 Cu1 O5 97.9(2) 3_676 . ? O2 Cu1 O5 94.5(2) . . ? O4 Cu1 O5 94.9(2) 4_686 . ? O3 Cu1 Cu1 83.79(15) 2_545 3_676 ? O1 Cu1 Cu1 83.42(15) 3_676 3_676 ? O2 Cu1 Cu1 84.20(14) . 3_676 ? O4 Cu1 Cu1 84.12(14) 4_686 3_676 ? O5 Cu1 Cu1 178.29(14) . 3_676 ? C1 O1 Cu1 123.6(4) . 3_676 ? C1 O2 Cu1 122.4(4) . . ? C21 O3 Cu1 123.4(4) . 2 ? C21 O4 Cu1 121.9(4) . 4_485 ? C22 O5 Cu1 121.3(5) . . ? C22 O5 H5A 119.4 . . ? Cu1 O5 H5A 119.4 . . ? C8 N1 C9 107.5(6) . . ? C8 N1 C5 125.6(6) . . ? C9 N1 C5 126.7(6) . . ? C8 N2 C10 109.4(6) . . ? C8 N2 C11 124.2(7) . . ? C10 N2 C11 126.3(7) . . ? C12 N3 C13 107.8(6) . . ? C12 N3 C11 128.2(7) . . ? C13 N3 C11 124.0(6) . . ? C12 N4 C14 109.1(6) . . ? C12 N4 C17 126.4(6) . . ? C14 N4 C17 124.3(6) . . ? O8 N5 O7 125.3(16) . . ? O8 N5 O6 108.3(14) . . ? O7 N5 O6 126.3(13) . . ? O11 N6 O9 119.2(9) . . ? O11 N6 O10 120.4(9) . . ? O9 N6 O10 120.3(8) . . ? O2 C1 O1 126.4(6) . . ? O2 C1 C2 117.4(6) . . ? O1 C1 C2 116.1(6) . . ? C3 C2 C7 119.1(6) . . ? C3 C2 C1 120.7(6) . . ? C7 C2 C1 120.1(6) . . ? C2 C3 C4 120.8(6) . . ? C2 C3 H3A 119.6 . . ? C4 C3 H3A 119.6 . . ? C5 C4 C3 119.3(6) . . ? C5 C4 H4A 120.3 . . ? C3 C4 H4A 120.3 . . ? C4 C5 C6 121.4(6) . . ? C4 C5 N1 120.9(6) . . ? C6 C5 N1 117.6(6) . . ? C7 C6 C5 118.7(6) . . ? C7 C6 H6A 120.6 . . ? C5 C6 H6A 120.6 . . ? C6 C7 C2 120.6(6) . . ? C6 C7 H7A 119.7 . . ? C2 C7 H7A 119.7 . . ? N2 C8 N1 108.1(6) . . ? N2 C8 H8A 125.9 . . ? N1 C8 H8A 125.9 . . ? C10 C9 N1 107.9(7) . . ? C10 C9 H9A 126.0 . . ? N1 C9 H9A 126.0 . . ? C9 C10 N2 107.1(7) . . ? C9 C10 H10A 126.4 . . ? N2 C10 H10A 126.4 . . ? N3 C11 N2 110.4(5) . . ? N3 C11 H11A 109.6 . . ? N2 C11 H11A 109.6 . . ? N3 C11 H11B 109.6 . . ? N2 C11 H11B 109.6 . . ? H11A C11 H11B 108.1 . . ? N3 C12 N4 108.2(7) . . ? N3 C12 H12A 125.9 . . ? N4 C12 H12A 125.9 . . ? C14 C13 N3 108.6(6) . . ? C14 C13 H13A 125.7 . . ? N3 C13 H13A 125.7 . . ? C13 C14 N4 106.3(7) . . ? C13 C14 H14A 126.9 . . ? N4 C14 H14A 126.9 . . ? C16 C15 C20 120.4(6) . . ? C16 C15 H15A 119.8 . . ? C20 C15 H15A 119.8 . . ? C17 C16 C15 119.6(7) . . ? C17 C16 H16A 120.2 . . ? C15 C16 H16A 120.2 . . ? C16 C17 C18 121.5(6) . . ? C16 C17 N4 119.1(6) . . ? C18 C17 N4 119.4(6) . . ? C19 C18 C17 118.0(6) . . ? C19 C18 H18A 121.0 . . ? C17 C18 H18A 121.0 . . ? C18 C19 C20 120.9(7) . . ? C18 C19 H19A 119.5 . . ? C20 C19 H19A 119.5 . . ? C15 C20 C19 119.5(6) . . ? C15 C20 C21 120.5(6) . . ? C19 C20 C21 120.0(6) . . ? O4 C21 O3 126.7(6) . . ? O4 C21 C20 117.4(6) . . ? O3 C21 C20 115.8(6) . . ? O5 C22 H22A 109.5 . . ? O5 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O5 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.951 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.951 _refine_diff_density_max 0.897 _refine_diff_density_min -0.292 _refine_diff_density_rms 0.113 # Attachment '- New2.cif' data_New2 _database_code_depnum_ccdc_archive 'CCDC 808137' #TrackingRef '- New2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H18 Cl2 Cu N4 O5' _chemical_formula_weight 540.83 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' 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 P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.7438(7) _cell_length_b 14.3440(7) _cell_length_c 13.8748(6) _cell_angle_alpha 90.00 _cell_angle_beta 98.959(5) _cell_angle_gamma 90.00 _cell_volume 2112.15(19) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 10353 _cell_measurement_theta_min 3.21 _cell_measurement_theta_max 26.37 _exptl_crystal_description bloc _exptl_crystal_colour green _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.701 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1100 _exptl_absorpt_coefficient_mu 1.331 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.750 _exptl_absorpt_correction_T_max 0.911 _exptl_absorpt_process_details CrysAlisPro _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 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3592 _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% ? _diffrn_reflns_number 10353 _diffrn_reflns_av_R_equivalents 0.0497 _diffrn_reflns_av_sigmaI/netI 0.1236 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.21 _diffrn_reflns_theta_max 26.37 _reflns_number_total 4309 _reflns_number_gt 1978 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro (Oxford Diffraction Ltd., 2010)' _computing_cell_refinement 'CrysAlisPro (Oxford Diffraction Ltd., 2010)' _computing_data_reduction 'CrysAlisPro (Oxford Diffraction Ltd., 2010)' _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^)+(0.0039P)^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_number_reflns 4309 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1084 _refine_ls_R_factor_gt 0.0438 _refine_ls_wR_factor_ref 0.0532 _refine_ls_wR_factor_gt 0.0495 _refine_ls_goodness_of_fit_ref 0.902 _refine_ls_restrained_S_all 0.902 _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 -0.17654(5) 0.39638(3) 0.65911(3) 0.04487(14) Uani 1 1 d . . . Cl1 Cl 0.03123(10) 0.38437(8) 0.72535(7) 0.0648(3) Uani 1 1 d . . . Cl2 Cl -0.37341(11) 0.43879(8) 0.59741(7) 0.0686(3) Uani 1 1 d . . . O1 O -0.6267(2) 0.10572(18) 2.02911(15) 0.0536(7) Uani 1 1 d . . . O2 O -0.6846(3) 0.25239(17) 2.03548(17) 0.0538(8) Uani 1 1 d . . . O3 O -0.2300(2) 0.37508(17) 0.78388(16) 0.0506(7) Uani 1 1 d . . . O4 O -0.2200(3) 0.52819(18) 0.80544(17) 0.0579(8) Uani 1 1 d . . . O101 O -0.1871(3) 0.57190(16) 0.4473(2) 0.0677(8) Uani 1 1 d . . . H10B H -0.1657 0.5071 0.4632 0.081 Uiso 1 1 d . . . H10C H -0.1098 0.5726 0.4201 0.081 Uiso 1 1 d . . . N1 N -0.5540(3) 0.2273(2) 1.5991(2) 0.0438(9) Uani 1 1 d . . . N2 N -0.5724(3) 0.2730(2) 1.4487(2) 0.0441(9) Uani 1 1 d . . . N3 N -0.5207(3) 0.35744(19) 1.3104(2) 0.0392(8) Uani 1 1 d . . . N4 N -0.4200(3) 0.3991(2) 1.19477(18) 0.0384(7) Uani 1 1 d . . . C1 C -0.6475(4) 0.1875(3) 1.9931(3) 0.0413(10) Uani 1 1 d . . . C2 C -0.6181(4) 0.1979(2) 1.8895(3) 0.0396(10) Uani 1 1 d . . . C3 C -0.6780(4) 0.2664(2) 1.8304(3) 0.0485(11) Uani 1 1 d . . . H3A H -0.7341 0.3062 1.8547 0.058 Uiso 1 1 calc R . . C4 C -0.6561(4) 0.2770(2) 1.7353(3) 0.0503(11) Uani 1 1 d . . . H4A H -0.6982 0.3231 1.6958 0.060 Uiso 1 1 calc R . . C5 C -0.5725(4) 0.2196(2) 1.6997(3) 0.0385(9) Uani 1 1 d . . . C6 C -0.5127(4) 0.1504(3) 1.7565(3) 0.0526(12) Uani 1 1 d . . . H6A H -0.4578 0.1103 1.7314 0.063 Uiso 1 1 calc R . . C7 C -0.5345(4) 0.1402(2) 1.8522(3) 0.0505(11) Uani 1 1 d . . . H7A H -0.4923 0.0940 1.8915 0.061 Uiso 1 1 calc R . . C8 C -0.4864(4) 0.1661(3) 1.5497(3) 0.0591(12) Uani 1 1 d . . . H8A H -0.4409 0.1146 1.5764 0.071 Uiso 1 1 calc R . . C9 C -0.4986(4) 0.1942(3) 1.4571(3) 0.0537(12) Uani 1 1 d . . . H9A H -0.4635 0.1658 1.4074 0.064 Uiso 1 1 calc R . . C10 C -0.6045(4) 0.2922(3) 1.5360(3) 0.0480(11) Uani 1 1 d . . . H10A H -0.6537 0.3422 1.5502 0.058 Uiso 1 1 calc R . . C11 C -0.6235(4) 0.3227(3) 1.3585(3) 0.0504(11) Uani 1 1 d . . . H11A H -0.6764 0.2810 1.3149 0.060 Uiso 1 1 calc R . . H11B H -0.6750 0.3746 1.3738 0.060 Uiso 1 1 calc R . . C12 C -0.4226(4) 0.4119(3) 1.3519(3) 0.0471(11) Uani 1 1 d . . . H12A H -0.4034 0.4282 1.4173 0.057 Uiso 1 1 calc R . . C13 C -0.3590(4) 0.4375(2) 1.2796(3) 0.0453(10) Uani 1 1 d . . . H13A H -0.2869 0.4744 1.2862 0.054 Uiso 1 1 calc R . . C14 C -0.5176(4) 0.3505(2) 1.2152(2) 0.0432(11) Uani 1 1 d . . . H14A H -0.5742 0.3172 1.1705 0.052 Uiso 1 1 calc R . . C15 C -0.3001(4) 0.5086(3) 0.9892(3) 0.0539(12) Uani 1 1 d . . . H15A H -0.2731 0.5672 0.9725 0.065 Uiso 1 1 calc R . . C16 C -0.3413(4) 0.4958(2) 1.0772(3) 0.0547(12) Uani 1 1 d . . . H16A H -0.3412 0.5455 1.1203 0.066 Uiso 1 1 calc R . . C17 C -0.3819(3) 0.4112(2) 1.1010(2) 0.0389(10) Uani 1 1 d . . . C18 C -0.3848(3) 0.3371(3) 1.0384(3) 0.0439(11) Uani 1 1 d . . . H18A H -0.4135 0.2792 1.0556 0.053 Uiso 1 1 calc R . . C19 C -0.3442(3) 0.3494(2) 0.9488(3) 0.0427(11) Uani 1 1 d . . . H19A H -0.3482 0.3000 0.9050 0.051 Uiso 1 1 calc R . . C20 C -0.2986(3) 0.4340(3) 0.9247(2) 0.0402(10) Uani 1 1 d . . . C21 C -0.2456(4) 0.4504(3) 0.8300(2) 0.0452(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 0.0548(4) 0.0505(3) 0.0317(2) 0.0001(2) 0.0140(2) 0.0027(3) Cl1 0.0531(8) 0.0938(8) 0.0487(6) 0.0121(6) 0.0121(5) 0.0051(7) Cl2 0.0627(9) 0.0886(8) 0.0528(7) -0.0116(6) 0.0032(6) 0.0119(7) O1 0.067(2) 0.0638(18) 0.0329(15) -0.0021(15) 0.0171(14) 0.0017(18) O2 0.075(2) 0.0504(17) 0.0397(16) -0.0109(13) 0.0218(15) 0.0041(15) O3 0.060(2) 0.0548(19) 0.0402(15) 0.0015(14) 0.0193(14) 0.0065(15) O4 0.078(2) 0.0564(19) 0.0448(17) 0.0008(14) 0.0260(15) -0.0201(16) O101 0.059(2) 0.0608(19) 0.087(2) 0.0091(15) 0.0224(16) 0.0078(15) N1 0.049(3) 0.051(2) 0.0334(18) 0.0023(17) 0.0119(17) 0.0010(18) N2 0.043(2) 0.057(2) 0.0349(19) 0.0014(16) 0.0129(17) -0.0048(18) N3 0.040(2) 0.048(2) 0.0302(18) 0.0003(14) 0.0079(16) 0.0008(17) N4 0.046(2) 0.0422(18) 0.0285(16) 0.0007(16) 0.0095(15) -0.0016(18) C1 0.033(3) 0.043(3) 0.046(3) 0.010(2) 0.001(2) -0.010(2) C2 0.044(3) 0.040(2) 0.035(2) -0.0025(19) 0.008(2) -0.008(2) C3 0.060(3) 0.051(3) 0.036(2) 0.002(2) 0.013(2) 0.006(2) C4 0.061(3) 0.051(3) 0.040(2) 0.005(2) 0.010(2) 0.018(2) C5 0.039(3) 0.049(2) 0.028(2) -0.001(2) 0.0057(18) 0.000(2) C6 0.061(3) 0.058(3) 0.043(2) 0.004(2) 0.020(2) 0.016(2) C7 0.061(3) 0.053(3) 0.036(2) 0.0065(19) 0.005(2) 0.011(2) C8 0.062(3) 0.073(3) 0.046(3) 0.002(2) 0.021(2) 0.022(2) C9 0.063(3) 0.063(3) 0.039(2) 0.001(2) 0.022(2) 0.016(3) C10 0.056(3) 0.052(3) 0.039(2) 0.001(2) 0.015(2) -0.005(2) C11 0.046(3) 0.065(3) 0.041(2) 0.024(2) 0.013(2) -0.002(2) C12 0.049(3) 0.060(3) 0.031(2) -0.003(2) 0.002(2) -0.005(2) C13 0.038(3) 0.055(3) 0.042(2) -0.006(2) 0.004(2) -0.009(2) C14 0.053(3) 0.045(2) 0.032(2) 0.0011(18) 0.007(2) -0.004(2) C15 0.075(3) 0.043(2) 0.049(3) 0.000(2) 0.026(2) -0.011(2) C16 0.078(4) 0.043(3) 0.048(2) -0.006(2) 0.025(2) -0.002(2) C17 0.047(3) 0.039(3) 0.033(2) 0.0016(19) 0.0170(19) -0.003(2) C18 0.045(3) 0.044(2) 0.045(2) 0.006(2) 0.014(2) -0.003(2) C19 0.044(3) 0.045(2) 0.042(2) -0.0081(19) 0.014(2) -0.009(2) C20 0.042(3) 0.044(2) 0.036(2) -0.001(2) 0.0095(19) -0.004(2) C21 0.048(3) 0.055(3) 0.034(2) -0.001(2) 0.008(2) 0.002(2) _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 1.931(2) . ? Cu1 O1 1.960(2) 4_664 ? Cu1 Cl2 2.2389(13) . ? Cu1 Cl1 2.2843(12) . ? O1 C1 1.281(4) . ? O1 Cu1 1.960(2) 4_567 ? O2 C1 1.201(4) . ? O3 C21 1.280(4) . ? O4 C21 1.211(4) . ? O101 H10B 0.9746 . ? O101 H10C 0.9637 . ? N1 C10 1.334(4) . ? N1 C8 1.386(4) . ? N1 C5 1.445(4) . ? N2 C10 1.339(4) . ? N2 C9 1.375(4) . ? N2 C11 1.471(4) . ? N3 C14 1.330(4) . ? N3 C12 1.365(4) . ? N3 C11 1.464(4) . ? N4 C14 1.326(4) . ? N4 C13 1.370(4) . ? N4 C17 1.433(4) . ? C1 C2 1.527(4) . ? C2 C3 1.374(4) . ? C2 C7 1.379(4) . ? C3 C4 1.385(4) . ? C3 H3A 0.9300 . ? C4 C5 1.366(4) . ? C4 H4A 0.9300 . ? C5 C6 1.365(4) . ? C6 C7 1.392(4) . ? C6 H6A 0.9300 . ? C7 H7A 0.9300 . ? C8 C9 1.334(5) . ? C8 H8A 0.9300 . ? C9 H9A 0.9300 . ? C10 H10A 0.9300 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.349(4) . ? C12 H12A 0.9300 . ? C13 H13A 0.9300 . ? C14 H14A 0.9300 . ? C15 C16 1.374(4) . ? C15 C20 1.397(4) . ? C15 H15A 0.9300 . ? C16 C17 1.349(4) . ? C16 H16A 0.9300 . ? C17 C18 1.370(4) . ? C18 C19 1.391(4) . ? C18 H18A 0.9300 . ? C19 C20 1.369(4) . ? C19 H19A 0.9300 . ? C20 C21 1.529(4) . ? 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 169.88(11) . 4_664 ? O3 Cu1 Cl2 89.45(8) . . ? O1 Cu1 Cl2 91.69(8) 4_664 . ? O3 Cu1 Cl1 92.06(9) . . ? O1 Cu1 Cl1 88.80(8) 4_664 . ? Cl2 Cu1 Cl1 168.56(5) . . ? C1 O1 Cu1 108.5(2) . 4_567 ? C21 O3 Cu1 113.3(2) . . ? H10B O101 H10C 84.9 . . ? C10 N1 C8 108.0(3) . . ? C10 N1 C5 125.8(3) . . ? C8 N1 C5 126.2(3) . . ? C10 N2 C9 108.6(3) . . ? C10 N2 C11 123.7(3) . . ? C9 N2 C11 127.3(3) . . ? C14 N3 C12 108.9(3) . . ? C14 N3 C11 124.4(3) . . ? C12 N3 C11 126.2(3) . . ? C14 N4 C13 108.4(3) . . ? C14 N4 C17 127.2(3) . . ? C13 N4 C17 124.4(3) . . ? O2 C1 O1 124.7(3) . . ? O2 C1 C2 121.2(3) . . ? O1 C1 C2 114.0(4) . . ? C3 C2 C7 118.5(3) . . ? C3 C2 C1 119.0(3) . . ? C7 C2 C1 122.5(4) . . ? C2 C3 C4 120.9(3) . . ? C2 C3 H3A 119.6 . . ? C4 C3 H3A 119.6 . . ? C5 C4 C3 119.8(4) . . ? C5 C4 H4A 120.1 . . ? C3 C4 H4A 120.1 . . ? C6 C5 C4 120.5(3) . . ? C6 C5 N1 119.3(3) . . ? C4 C5 N1 120.0(3) . . ? C5 C6 C7 119.5(3) . . ? C5 C6 H6A 120.2 . . ? C7 C6 H6A 120.2 . . ? C2 C7 C6 120.7(4) . . ? C2 C7 H7A 119.6 . . ? C6 C7 H7A 119.6 . . ? C9 C8 N1 107.7(4) . . ? C9 C8 H8A 126.2 . . ? N1 C8 H8A 126.2 . . ? C8 C9 N2 107.4(3) . . ? C8 C9 H9A 126.3 . . ? N2 C9 H9A 126.3 . . ? N1 C10 N2 108.4(3) . . ? N1 C10 H10A 125.8 . . ? N2 C10 H10A 125.8 . . ? N3 C11 N2 110.1(3) . . ? N3 C11 H11A 109.6 . . ? N2 C11 H11A 109.6 . . ? N3 C11 H11B 109.6 . . ? N2 C11 H11B 109.6 . . ? H11A C11 H11B 108.1 . . ? C13 C12 N3 106.9(3) . . ? C13 C12 H12A 126.6 . . ? N3 C12 H12A 126.6 . . ? C12 C13 N4 107.4(3) . . ? C12 C13 H13A 126.3 . . ? N4 C13 H13A 126.3 . . ? N4 C14 N3 108.4(3) . . ? N4 C14 H14A 125.8 . . ? N3 C14 H14A 125.8 . . ? C16 C15 C20 120.3(3) . . ? C16 C15 H15A 119.9 . . ? C20 C15 H15A 119.9 . . ? C17 C16 C15 120.0(3) . . ? C17 C16 H16A 120.0 . . ? C15 C16 H16A 120.0 . . ? C16 C17 C18 121.3(3) . . ? C16 C17 N4 118.7(3) . . ? C18 C17 N4 120.0(3) . . ? C17 C18 C19 119.3(3) . . ? C17 C18 H18A 120.4 . . ? C19 C18 H18A 120.4 . . ? C20 C19 C18 120.3(3) . . ? C20 C19 H19A 119.8 . . ? C18 C19 H19A 119.8 . . ? C19 C20 C15 118.9(3) . . ? C19 C20 C21 122.8(3) . . ? C15 C20 C21 118.4(3) . . ? O4 C21 O3 125.7(3) . . ? O4 C21 C20 121.0(3) . . ? O3 C21 C20 113.3(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 O101 H10B O1 0.97 1.87 2.824(4) 164.0 4_664 O101 H10C Cl1 0.96 2.39 3.191(3) 140.6 3_566 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.594 _refine_diff_density_min -0.374 _refine_diff_density_rms 0.058