data_1 _audit_creation_date 2020-04-28 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _shelx_SHELXL_version_number '2018/3' _audit_contact_author_address ? _audit_contact_author_email ? _audit_contact_author_name '' _audit_contact_author_phone ? _publ_contact_author_id_orcid ? _publ_section_references ; Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H. (2009), J. Appl. Cryst. 42, 339-341. Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8. ; _chemical_name_common ? _chemical_name_systematic ? _chemical_formula_moiety '0.5(C90 H62 Cu4 N10 O26), H2 O' _chemical_formula_sum 'C45 H33 Cu2 N5 O14' _chemical_formula_weight 994.84 _chemical_melting_point ? 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' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _space_group_crystal_system 'monoclinic' _space_group_IT_number 12 _space_group_name_H-M_alt 'C 1 2/m 1' _space_group_name_Hall '-C 2y' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z' _cell_length_a 12.9216(3) _cell_length_b 23.8450(6) _cell_length_c 15.8873(4) _cell_angle_alpha 90 _cell_angle_beta 111.9170(13) _cell_angle_gamma 90 _cell_volume 4541.3(2) _cell_formula_units_Z 4 _cell_measurement_reflns_used 9896 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 27.61 _cell_measurement_theta_min 2.67 _shelx_estimated_absorpt_T_max 0.745 _shelx_estimated_absorpt_T_min 0.700 _exptl_absorpt_coefficient_mu 1.009 _exptl_absorpt_correction_T_max 0.973 _exptl_absorpt_correction_T_min 0.824 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ? _exptl_absorpt_special_details ? _exptl_crystal_colour blue _exptl_crystal_colour_primary blue _exptl_crystal_density_diffrn 1.455 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_description block _exptl_crystal_F_000 2032 _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.31 _exptl_transmission_factor_max ? _exptl_transmission_factor_min ? _diffrn_reflns_av_R_equivalents 0.0528 _diffrn_reflns_av_unetI/netI 0.0507 _diffrn_reflns_Laue_measured_fraction_full 0.994 _diffrn_reflns_Laue_measured_fraction_max 0.985 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 19790 _diffrn_reflns_point_group_measured_fraction_full 0.994 _diffrn_reflns_point_group_measured_fraction_max 0.985 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.936 _diffrn_reflns_theta_min 2.197 _diffrn_ambient_temperature 296.15 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.985 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'Enhance (Mo) X-ray Source' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 4821 _reflns_number_total 5495 _reflns_odcompleteness_iscentric 1 _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _reflns_threshold_expression 'I > 2\s(I)' _computing_cell_refinement ? _computing_data_collection ? _computing_data_reduction ? _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution ? _refine_diff_density_max 1.500 _refine_diff_density_min -1.126 _refine_diff_density_rms 0.143 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 312 _refine_ls_number_reflns 5495 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0533 _refine_ls_R_factor_gt 0.0482 _refine_ls_restrained_S_all 1.049 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1053P)^2^+7.9472P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1542 _refine_ls_wR_factor_ref 0.1586 _refine_special_details ? _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, H8A of O8, H7 of O7 At 1.5 times of: H1 of O1 2.a Riding coordinates: O1(H1), O7(H7), O8(H8A) 2.b Aromatic/amide H refined with riding coordinates: C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12), C14(H14), C15(H15), C17(H17), C18(H18), C20(H20), C21(H21), C23(H23), C24(H24) ; _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary ? _atom_sites_solution_secondary ? 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.000000 0.43272(2) 0.000000 0.01223(14) Uani 1 2 d S T P . . Cu2 Cu 0.09210(3) 0.500000 0.19088(2) 0.01042(13) Uani 1 2 d S T P . . C1 C 0.9190(2) 0.66554(12) 0.08054(17) 0.0181(5) Uani 1 1 d . . . . . C2 C 0.8198(2) 0.63484(12) 0.17939(19) 0.0221(5) Uani 1 1 d . . . . . H2 H 0.853053 0.599815 0.183791 0.026 Uiso 1 1 calc R . . . . C3 C 0.7484(2) 0.64524(13) 0.2240(2) 0.0256(6) Uani 1 1 d . . . . . H3 H 0.733150 0.617246 0.258500 0.031 Uiso 1 1 calc R . . . . C4 C 0.6999(2) 0.69744(13) 0.21729(17) 0.0199(5) Uani 1 1 d . . . . . C5 C 0.7211(2) 0.73943(12) 0.16647(19) 0.0207(5) Uani 1 1 d . . . . . H5 H 0.688239 0.774526 0.162673 0.025 Uiso 1 1 calc R . . . . C6 C 0.7913(2) 0.72877(12) 0.12143(18) 0.0200(5) Uani 1 1 d . . . . . H6 H 0.805380 0.756689 0.086223 0.024 Uiso 1 1 calc R . . . . C7 C 0.6452(2) 0.75066(12) 0.32410(17) 0.0192(5) Uani 1 1 d . . . . . C8 C 0.5587(2) 0.77809(13) 0.34011(18) 0.0218(5) Uani 1 1 d . . . . . H8 H 0.485044 0.768850 0.305568 0.026 Uiso 1 1 calc R . . . . C9 C 0.5808(3) 0.81823(13) 0.40572(19) 0.0261(6) Uani 1 1 d . . . . . H9 H 0.522807 0.835147 0.417627 0.031 Uiso 1 1 calc R . . . . C10 C 0.6894(3) 0.83342(13) 0.45403(18) 0.0267(6) Uani 1 1 d . . . . . C11 C 0.7772(2) 0.80914(14) 0.43677(18) 0.0268(6) Uani 1 1 d . . . . . H11 H 0.850077 0.820936 0.468363 0.032 Uiso 1 1 calc R . . . . C12 C 0.7555(2) 0.76776(14) 0.37292(19) 0.0251(6) Uani 1 1 d . . . . . H12 H 0.814012 0.750856 0.361766 0.030 Uiso 1 1 calc R . . . . C13 C 0.5256(2) 0.67555(12) 0.23453(17) 0.0181(5) Uani 1 1 d . . . . . C14 C 0.4723(2) 0.66017(12) 0.14524(18) 0.0200(5) Uani 1 1 d . . . . . H14 H 0.501809 0.670602 0.102402 0.024 Uiso 1 1 calc R . . . . C15 C 0.3748(2) 0.62923(12) 0.11904(17) 0.0188(5) Uani 1 1 d . . . . . H15 H 0.338791 0.619213 0.058498 0.023 Uiso 1 1 calc R . . . . C16 C 0.3309(2) 0.61319(11) 0.18192(17) 0.0160(5) Uani 1 1 d . . . . . C17 C 0.3855(2) 0.62786(12) 0.27142(17) 0.0172(5) Uani 1 1 d . . . . . H17 H 0.356475 0.616931 0.314359 0.021 Uiso 1 1 calc R . . . . C18 C 0.4825(2) 0.65852(13) 0.29794(17) 0.0210(6) Uani 1 1 d . . . . . H18 H 0.519178 0.667826 0.358722 0.025 Uiso 1 1 calc R . . . . C19 C 0.2249(2) 0.58022(12) 0.15438(17) 0.0165(5) Uani 1 1 d . . . . . C20 C 0.1347(3) 0.500000 0.3793(2) 0.0237(8) Uani 1 2 d S T P . . H20 H 0.207421 0.500000 0.381091 0.028 Uiso 1 2 calc RS T P . . C21 C 0.1178(3) 0.500000 0.4591(2) 0.0217(8) Uani 1 2 d S T P . . H21 H 0.178377 0.500000 0.514047 0.026 Uiso 1 2 calc RS T P . . C22 C 0.0108(3) 0.500000 0.4577(2) 0.0139(6) Uani 1 2 d S T P . . C23 C -0.0759(3) 0.500000 0.3742(2) 0.0173(7) Uani 1 2 d S T P . . H23 H -0.149363 0.500000 0.370651 0.021 Uiso 1 2 calc RS T P . . C24 C -0.0532(3) 0.500000 0.2970(2) 0.0170(7) Uani 1 2 d S T P . . H24 H -0.112138 0.500000 0.241022 0.020 Uiso 1 2 calc RS T P . . C25 C 0.8415(2) 0.67665(11) 0.12808(17) 0.0168(5) Uani 1 1 d . . . . . N1 N 0.62374(18) 0.70790(11) 0.26121(16) 0.0214(5) Uani 1 1 d . . . . . N2 N 0.7130(3) 0.87401(13) 0.52479(19) 0.0407(8) Uani 1 1 d . . . . . N3 N 0.0512(2) 0.500000 0.2995(2) 0.0159(6) Uani 1 2 d S T P . . O1 O 0.9299(2) 0.70581(10) 0.03231(17) 0.0337(5) Uani 1 1 d . . . . . H1 H 0.857389 0.696688 -0.022417 0.051 Uiso 1 1 d R . . A 1 O2 O 0.96736(17) 0.61981(9) 0.09056(13) 0.0234(4) Uani 1 1 d . . . . . O3 O 0.8056(3) 0.89751(14) 0.5527(2) 0.0676(10) Uani 1 1 d . . . . . O4 O 0.6401(3) 0.88491(12) 0.55376(17) 0.0516(8) Uani 1 1 d . . . . . O5 O 0.17184(15) 0.57200(10) 0.07285(13) 0.0237(5) Uani 1 1 d . . . . . O6 O 0.19784(16) 0.56192(9) 0.21714(13) 0.0233(4) Uani 1 1 d . . . . . O7 O -0.02240(18) 0.500000 0.07472(15) 0.0117(5) Uani 1 2 d S T P . . H7 H -0.086595 0.500000 0.076937 0.014 Uiso 1 2 d RS T P . . O8 O 0.2467(3) 0.500000 -0.0529(4) 0.0609(12) Uani 1 2 d S T P . . H8A H 0.266348 0.529590 -0.021891 0.073 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 0.0126(2) 0.0136(2) 0.0107(2) 0.000 0.00464(16) 0.000 Cu2 0.0111(2) 0.0161(2) 0.0058(2) 0.000 0.00524(15) 0.000 C1 0.0162(11) 0.0218(14) 0.0173(12) -0.0037(10) 0.0074(9) -0.0008(9) C2 0.0247(13) 0.0185(14) 0.0248(13) 0.0001(10) 0.0114(11) 0.0006(10) C3 0.0280(14) 0.0268(16) 0.0277(14) 0.0016(11) 0.0167(12) -0.0055(11) C4 0.0130(11) 0.0310(16) 0.0174(11) -0.0062(10) 0.0074(9) -0.0062(10) C5 0.0198(12) 0.0201(14) 0.0246(13) -0.0035(10) 0.0109(10) 0.0007(10) C6 0.0181(12) 0.0218(14) 0.0228(12) 0.0005(10) 0.0108(10) -0.0017(10) C7 0.0204(12) 0.0225(14) 0.0156(11) -0.0038(10) 0.0078(10) -0.0073(10) C8 0.0201(12) 0.0242(15) 0.0200(12) -0.0039(10) 0.0063(10) -0.0034(10) C9 0.0315(15) 0.0241(15) 0.0206(13) -0.0032(11) 0.0073(11) 0.0028(11) C10 0.0390(16) 0.0178(14) 0.0164(12) -0.0031(10) 0.0022(11) -0.0037(11) C11 0.0263(14) 0.0286(16) 0.0192(12) -0.0004(11) 0.0013(11) -0.0130(11) C12 0.0211(13) 0.0335(17) 0.0217(13) -0.0028(11) 0.0093(11) -0.0096(11) C13 0.0137(11) 0.0210(14) 0.0207(12) -0.0049(10) 0.0075(9) -0.0062(9) C14 0.0221(12) 0.0224(14) 0.0197(12) -0.0048(10) 0.0126(10) -0.0065(10) C15 0.0171(11) 0.0240(14) 0.0144(11) -0.0049(10) 0.0048(9) -0.0032(10) C16 0.0136(11) 0.0166(13) 0.0174(11) -0.0009(9) 0.0053(9) -0.0005(9) C17 0.0166(11) 0.0206(13) 0.0158(12) -0.0033(9) 0.0079(9) -0.0047(9) C18 0.0184(12) 0.0310(16) 0.0138(11) -0.0056(10) 0.0062(9) -0.0072(11) C19 0.0137(11) 0.0197(13) 0.0168(11) -0.0039(9) 0.0065(9) -0.0008(9) C20 0.0166(17) 0.043(3) 0.0145(17) 0.000 0.0089(14) 0.000 C21 0.0177(17) 0.036(2) 0.0116(15) 0.000 0.0062(13) 0.000 C22 0.0186(16) 0.0146(17) 0.0109(15) 0.000 0.0082(13) 0.000 C23 0.0146(15) 0.026(2) 0.0129(15) 0.000 0.0074(13) 0.000 C24 0.0171(16) 0.0221(19) 0.0121(15) 0.000 0.0057(13) 0.000 C25 0.0144(11) 0.0198(14) 0.0162(11) -0.0037(9) 0.0058(9) -0.0028(9) N1 0.0175(10) 0.0286(14) 0.0221(11) -0.0110(9) 0.0121(9) -0.0108(9) N2 0.0557(19) 0.0234(15) 0.0240(13) -0.0059(11) -0.0070(13) 0.0051(13) N3 0.0189(14) 0.0187(16) 0.0129(13) 0.000 0.0092(11) 0.000 O1 0.0408(13) 0.0279(13) 0.0481(13) 0.0106(10) 0.0346(11) 0.0106(9) O2 0.0316(10) 0.0245(11) 0.0160(9) -0.0007(7) 0.0112(8) 0.0084(8) O3 0.0500(17) 0.0515(19) 0.0634(19) -0.0342(16) -0.0225(14) 0.0038(14) O4 0.088(2) 0.0358(16) 0.0266(12) -0.0101(11) 0.0166(13) 0.0122(14) O5 0.0147(9) 0.0401(13) 0.0161(9) -0.0072(8) 0.0056(7) -0.0100(8) O6 0.0218(9) 0.0305(12) 0.0183(9) -0.0028(8) 0.0083(7) -0.0112(8) O7 0.0098(10) 0.0163(13) 0.0101(10) 0.000 0.0049(8) 0.000 O8 0.0295(19) 0.045(3) 0.101(4) 0.000 0.016(2) 0.000 _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 O2 2.0663(19) 5_665 ? Cu1 O2 2.0663(19) 6_465 ? Cu1 O5 2.0890(18) 6_565 ? Cu1 O5 2.0890(18) 5_565 ? Cu1 O7 2.0793(15) . ? Cu1 O7 2.0793(15) 5_565 ? Cu2 N3 1.984(3) . ? Cu2 O6 1.9482(19) . ? Cu2 O6 1.9482(19) 6_565 ? Cu2 O7 1.886(2) . ? C1 C25 1.485(3) . ? C1 O1 1.269(4) . ? C1 O2 1.237(3) . ? C2 H2 0.9300 . ? C2 C3 1.379(4) . ? C2 C25 1.382(4) . ? C3 H3 0.9300 . ? C3 C4 1.380(4) . ? C4 C5 1.376(4) . ? C4 N1 1.425(3) . ? C5 H5 0.9300 . ? C5 C6 1.373(4) . ? C6 H6 0.9300 . ? C6 C25 1.388(4) . ? C7 C8 1.399(4) . ? C7 C12 1.405(4) . ? C7 N1 1.381(3) . ? C8 H8 0.9300 . ? C8 C9 1.365(4) . ? C9 H9 0.9300 . ? C9 C10 1.374(4) . ? C10 C11 1.389(5) . ? C10 N2 1.428(4) . ? C11 H11 0.9300 . ? C11 C12 1.367(4) . ? C12 H12 0.9300 . ? C13 C14 1.376(4) . ? C13 C18 1.382(4) . ? C13 N1 1.408(3) . ? C14 H14 0.9300 . ? C14 C15 1.382(4) . ? C15 H15 0.9300 . ? C15 C16 1.375(4) . ? C16 C17 1.376(3) . ? C16 C19 1.496(3) . ? C17 H17 0.9300 . ? C17 C18 1.374(3) . ? C18 H18 0.9300 . ? C19 O5 1.234(3) . ? C19 O6 1.252(3) . ? C20 H20 0.9300 . ? C20 C21 1.363(5) . ? C20 N3 1.324(5) . ? C21 H21 0.9300 . ? C21 C22 1.376(5) . ? C22 C22 1.470(6) 5_566 ? C22 C23 1.380(5) . ? C23 H23 0.9300 . ? C23 C24 1.364(5) . ? C24 H24 0.9300 . ? C24 N3 1.335(5) . ? N2 O3 1.243(5) . ? N2 O4 1.221(5) . ? O1 H1 1.0360 . ? O7 H7 0.8432 . ? O8 H8A 0.8437 6_565 ? O8 H8A 0.8437 . ? 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 O2 Cu1 O2 105.37(12) 5_665 6_465 ? O2 Cu1 O5 84.39(8) 5_665 6_565 ? O2 Cu1 O5 91.87(8) 6_465 6_565 ? O2 Cu1 O5 91.87(8) 5_665 5_565 ? O2 Cu1 O5 84.39(8) 6_465 5_565 ? O2 Cu1 O7 166.73(8) 5_665 . ? O2 Cu1 O7 87.83(7) 5_665 5_565 ? O2 Cu1 O7 87.83(7) 6_465 . ? O2 Cu1 O7 166.73(8) 6_465 5_565 ? O5 Cu1 O5 173.83(13) 5_565 6_565 ? O7 Cu1 O5 94.07(9) . 6_565 ? O7 Cu1 O5 90.70(8) . 5_565 ? O7 Cu1 O5 94.07(9) 5_565 5_565 ? O7 Cu1 O5 90.70(8) 5_565 6_565 ? O7 Cu1 O7 79.00(10) . 5_565 ? O6 Cu2 N3 101.95(8) . . ? O6 Cu2 N3 101.95(8) 6_565 . ? O6 Cu2 O6 98.56(13) . 6_565 ? O7 Cu2 N3 118.98(11) . . ? O7 Cu2 O6 116.16(7) . 6_565 ? O7 Cu2 O6 116.16(7) . . ? O1 C1 C25 114.8(2) . . ? O2 C1 C25 119.7(2) . . ? O2 C1 O1 125.4(2) . . ? C3 C2 H2 120.1 . . ? C3 C2 C25 119.7(3) . . ? C25 C2 H2 120.1 . . ? C2 C3 H3 120.2 . . ? C2 C3 C4 119.6(3) . . ? C4 C3 H3 120.2 . . ? C3 C4 N1 119.8(3) . . ? C5 C4 C3 121.2(2) . . ? C5 C4 N1 119.0(3) . . ? C4 C5 H5 120.5 . . ? C6 C5 C4 119.1(3) . . ? C6 C5 H5 120.5 . . ? C5 C6 H6 119.8 . . ? C5 C6 C25 120.5(3) . . ? C25 C6 H6 119.8 . . ? C8 C7 C12 118.6(3) . . ? N1 C7 C8 121.2(2) . . ? N1 C7 C12 120.1(3) . . ? C7 C8 H8 119.6 . . ? C9 C8 C7 120.9(3) . . ? C9 C8 H8 119.6 . . ? C8 C9 H9 120.3 . . ? C8 C9 C10 119.4(3) . . ? C10 C9 H9 120.3 . . ? C9 C10 C11 121.3(3) . . ? C9 C10 N2 119.5(3) . . ? C11 C10 N2 119.2(3) . . ? C10 C11 H11 120.3 . . ? C12 C11 C10 119.4(3) . . ? C12 C11 H11 120.3 . . ? C7 C12 H12 119.9 . . ? C11 C12 C7 120.2(3) . . ? C11 C12 H12 119.9 . . ? C14 C13 C18 119.4(2) . . ? C14 C13 N1 120.3(2) . . ? C18 C13 N1 120.3(2) . . ? C13 C14 H14 119.9 . . ? C13 C14 C15 120.2(2) . . ? C15 C14 H14 119.9 . . ? C14 C15 H15 119.8 . . ? C16 C15 C14 120.4(2) . . ? C16 C15 H15 119.8 . . ? C15 C16 C17 119.3(2) . . ? C15 C16 C19 121.0(2) . . ? C17 C16 C19 119.7(2) . . ? C16 C17 H17 119.7 . . ? C18 C17 C16 120.6(2) . . ? C18 C17 H17 119.7 . . ? C13 C18 H18 119.9 . . ? C17 C18 C13 120.2(2) . . ? C17 C18 H18 119.9 . . ? O5 C19 C16 118.7(2) . . ? O5 C19 O6 124.7(2) . . ? O6 C19 C16 116.6(2) . . ? C21 C20 H20 118.8 . . ? N3 C20 H20 118.8 . . ? N3 C20 C21 122.4(3) . . ? C20 C21 H21 120.2 . . ? C20 C21 C22 119.6(3) . . ? C22 C21 H21 120.2 . . ? C21 C22 C22 121.2(4) . 5_566 ? C21 C22 C23 117.7(3) . . ? C23 C22 C22 121.1(4) . 5_566 ? C22 C23 H23 120.2 . . ? C24 C23 C22 119.7(3) . . ? C24 C23 H23 120.2 . . ? C23 C24 H24 119.1 . . ? N3 C24 C23 121.8(3) . . ? N3 C24 H24 119.1 . . ? C2 C25 C1 119.7(2) . . ? C2 C25 C6 119.9(2) . . ? C6 C25 C1 120.4(2) . . ? C7 N1 C4 119.6(2) . . ? C7 N1 C13 122.5(2) . . ? C13 N1 C4 117.8(2) . . ? O3 N2 C10 118.7(3) . . ? O4 N2 C10 118.2(3) . . ? O4 N2 O3 123.0(3) . . ? C20 N3 Cu2 116.6(2) . . ? C20 N3 C24 118.8(3) . . ? C24 N3 Cu2 124.7(2) . . ? C1 O1 H1 94.5 . . ? C1 O2 Cu1 132.01(17) . 5_665 ? C19 O5 Cu1 130.50(17) . 5_565 ? C19 O6 Cu2 118.41(17) . . ? Cu1 O7 Cu1 100.99(10) 5_565 . ? Cu1 O7 H7 111.9 5_565 . ? Cu1 O7 H7 111.9 . . ? Cu2 O7 Cu1 109.46(8) . . ? Cu2 O7 Cu1 109.46(8) . 5_565 ? Cu2 O7 H7 112.6 . . ? H8A O8 H8A 113.5 . 6_565 ? 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 C3 C4 C5 0.2(4) . . . . ? C2 C3 C4 N1 178.2(2) . . . . ? C3 C2 C25 C1 179.6(2) . . . . ? C3 C2 C25 C6 -0.2(4) . . . . ? C3 C4 C5 C6 0.4(4) . . . . ? C3 C4 N1 C7 122.1(3) . . . . ? C3 C4 N1 C13 -61.2(4) . . . . ? C4 C5 C6 C25 -0.9(4) . . . . ? C5 C4 N1 C7 -59.8(4) . . . . ? C5 C4 N1 C13 116.9(3) . . . . ? C5 C6 C25 C1 -179.0(2) . . . . ? C5 C6 C25 C2 0.8(4) . . . . ? C7 C8 C9 C10 2.7(5) . . . . ? C8 C7 C12 C11 2.1(4) . . . . ? C8 C7 N1 C4 152.6(3) . . . . ? C8 C7 N1 C13 -23.9(4) . . . . ? C8 C9 C10 C11 0.7(5) . . . . ? C8 C9 C10 N2 -177.9(3) . . . . ? C9 C10 C11 C12 -2.6(5) . . . . ? C9 C10 N2 O3 -162.5(3) . . . . ? C9 C10 N2 O4 15.9(5) . . . . ? C10 C11 C12 C7 1.1(5) . . . . ? C11 C10 N2 O3 18.9(5) . . . . ? C11 C10 N2 O4 -162.7(3) . . . . ? C12 C7 C8 C9 -4.1(4) . . . . ? C12 C7 N1 C4 -26.8(4) . . . . ? C12 C7 N1 C13 156.6(3) . . . . ? C13 C14 C15 C16 -0.5(4) . . . . ? C14 C13 C18 C17 -1.8(4) . . . . ? C14 C13 N1 C4 -36.4(4) . . . . ? C14 C13 N1 C7 140.2(3) . . . . ? C14 C15 C16 C17 -0.5(4) . . . . ? C14 C15 C16 C19 179.4(3) . . . . ? C15 C16 C17 C18 0.4(4) . . . . ? C15 C16 C19 O5 -6.6(4) . . . . ? C15 C16 C19 O6 172.0(3) . . . . ? C16 C17 C18 C13 0.8(4) . . . . ? C16 C19 O5 Cu1 -145.0(2) . . . 5_565 ? C16 C19 O6 Cu2 -160.26(18) . . . . ? C17 C16 C19 O5 173.3(3) . . . . ? C17 C16 C19 O6 -8.1(4) . . . . ? C18 C13 C14 C15 1.7(4) . . . . ? C18 C13 N1 C4 143.1(3) . . . . ? C18 C13 N1 C7 -40.3(4) . . . . ? C19 C16 C17 C18 -179.5(3) . . . . ? C20 C21 C22 C22 180.000(1) . . . 5_566 ? C20 C21 C22 C23 0.000(1) . . . . ? C21 C20 N3 Cu2 180.000(1) . . . . ? C21 C20 N3 C24 0.000(1) . . . . ? C21 C22 C23 C24 0.000(1) . . . . ? C22 C22 C23 C24 180.000(1) 5_566 . . . ? C22 C23 C24 N3 0.000(1) . . . . ? C23 C24 N3 Cu2 180.000(1) . . . . ? C23 C24 N3 C20 0.000(1) . . . . ? C25 C1 O2 Cu1 138.3(2) . . . 5_665 ? C25 C2 C3 C4 -0.3(4) . . . . ? N1 C4 C5 C6 -177.7(2) . . . . ? N1 C7 C8 C9 176.5(3) . . . . ? N1 C7 C12 C11 -178.4(3) . . . . ? N1 C13 C14 C15 -178.9(3) . . . . ? N1 C13 C18 C17 178.7(3) . . . . ? N2 C10 C11 C12 176.0(3) . . . . ? N3 Cu2 O7 Cu1 -125.08(7) . . . . ? N3 Cu2 O7 Cu1 125.08(7) . . . 5_565 ? N3 C20 C21 C22 0.000(1) . . . . ? O1 C1 C25 C2 177.3(3) . . . . ? O1 C1 C25 C6 -2.9(4) . . . . ? O1 C1 O2 Cu1 -42.3(4) . . . 5_665 ? O2 C1 C25 C2 -3.3(4) . . . . ? O2 C1 C25 C6 176.5(2) . . . . ? O5 C19 O6 Cu2 18.3(4) . . . . ? O6 Cu2 O7 Cu1 -112.52(8) 6_565 . . 5_565 ? O6 Cu2 O7 Cu1 -2.69(12) 6_565 . . . ? O6 Cu2 O7 Cu1 2.68(12) . . . 5_565 ? O6 Cu2 O7 Cu1 112.52(8) . . . . ? O6 C19 O5 Cu1 36.5(4) . . . 5_565 ? _olex2_submission_special_instructions 'No special instructions were received' 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 -0.015 -0.011 -0.003 3335 1269 ' ' _platon_squeeze_void_probe_radius 1.20 _platon_squeeze_details ?