# 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_requested_category FM _publ_contact_author_name 'Mikko M. Hanninen' _publ_contact_author_email mikko.m.hanninen@jyu.fi loop_ _publ_author_name 'Enrique Colacio' 'Jesus E. Perea-Buceta' 'Antonio J. Mota' 'Mikko M. Hanninen' 'Reijo Sillanpaa' # END of CIF data_cdr19-7 _database_code_depnum_ccdc_archive 'CCDC 840696' #TrackingRef '6845_web_deposit_cif_file_0_MikkoM.Hanninen_1314020541.Jesus_comm_CIFs.cif' _audit_creation_date 2009-08-11T10:08:16-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C25 H17 Cu2 N11 O1 S3, H2 O' _chemical_formula_sum 'C25 H19 Cu2 N11 O2 S3' _chemical_formula_weight 728.77 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.1051(2) _cell_length_b 11.3327(2) _cell_length_c 15.9497(3) _cell_angle_alpha 72.0390(10) _cell_angle_beta 87.5780(10) _cell_angle_gamma 83.1160(10) _cell_volume 1383.56(5) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 5639 _cell_measurement_theta_min 0.407 _cell_measurement_theta_max 28.283 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.749 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 1.812 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 2008)' _exptl_absorpt_correction_T_min 0.605 _exptl_absorpt_correction_T_max 0.696 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0338 _diffrn_reflns_av_unetI/netI 0.0423 _diffrn_reflns_number 16608 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.53 _diffrn_reflns_theta_max 26 _diffrn_reflns_theta_full 26 _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.991 _reflns_number_total 5378 _reflns_number_gt 4562 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^ > 2\s(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^)+(0.0198P)^2^+2.2390P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 5378 _refine_ls_number_parameters 403 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0437 _refine_ls_R_factor_gt 0.0338 _refine_ls_wR_factor_ref 0.0784 _refine_ls_wR_factor_gt 0.0742 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.04 _refine_ls_shift/su_max 0.015 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.55 _refine_diff_density_min -0.437 _refine_diff_density_rms 0.079 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.75031(4) 0.31712(3) 0.83335(2) 0.01670(9) Uani 1 1 d . . . Cu2 Cu 0.77199(4) 0.20382(3) 0.66023(2) 0.01670(9) Uani 1 1 d . . . S1 S 1.28107(9) 0.17466(7) 0.74879(6) 0.03058(19) Uani 1 1 d . . . S2 S 0.68799(11) -0.03410(8) 0.93975(5) 0.03148(19) Uani 1 1 d . . . S3 S 0.85909(11) 0.73427(7) 0.80015(6) 0.0333(2) Uani 1 1 d . . . O1 O 0.5606(3) 0.1714(2) 0.57631(13) 0.0243(5) Uani 1 1 d D . . H1AO H 0.501(4) 0.221(3) 0.5322(16) 0.029 Uiso 1 1 d D . . H1BO H 0.508(4) 0.105(2) 0.597(2) 0.029 Uiso 1 1 d D . . O2 O 0.5433(3) 0.8944(2) 0.65689(16) 0.0403(6) Uani 1 1 d D . . H2AO H 0.519(5) 0.815(2) 0.665(3) 0.048 Uiso 1 1 d D . . H2BO H 0.624(4) 0.885(4) 0.697(2) 0.048 Uiso 1 1 d D . . N1 N 0.7521(3) 0.2560(2) 0.96571(14) 0.0185(5) Uani 1 1 d . . . N2 N 0.5255(3) 0.3977(2) 0.85871(14) 0.0165(5) Uani 1 1 d . . . N3 N 0.5872(3) 0.4356(2) 0.67279(14) 0.0164(5) Uani 1 1 d . . . N4 N 0.6447(3) 0.3108(2) 0.72073(14) 0.0165(5) Uani 1 1 d D . . H4N H 0.550(3) 0.277(3) 0.7385(18) 0.02 Uiso 1 1 d D . . N5 N 0.8205(3) 0.3461(2) 0.55312(14) 0.0168(5) Uani 1 1 d . . . N6 N 0.9573(3) 0.1150(2) 0.61061(14) 0.0186(5) Uani 1 1 d . . . N7 N 0.4673(3) 0.6282(2) 0.64774(15) 0.0225(5) Uani 1 1 d . . . N8 N 0.5568(3) 0.6207(2) 0.57374(15) 0.0221(5) Uani 1 1 d . . . N9 N 0.9661(3) 0.2324(2) 0.81391(15) 0.0222(5) Uani 1 1 d . . . N10 N 0.7261(3) 0.0572(2) 0.75769(16) 0.0239(5) Uani 1 1 d . . . N11 N 0.8323(3) 0.5003(2) 0.78273(17) 0.0281(6) Uani 1 1 d . . . C1 C 0.8746(4) 0.1801(3) 1.01505(18) 0.0227(6) Uani 1 1 d . . . H1 H 0.9772 0.1632 0.9876 0.027 Uiso 1 1 calc R . . C2 C 0.8563(4) 0.1253(3) 1.10505(19) 0.0240(6) Uani 1 1 d . . . H2 H 0.945 0.0717 1.1388 0.029 Uiso 1 1 calc R . . C3 C 0.7077(4) 0.1499(3) 1.14458(19) 0.0259(7) Uani 1 1 d . . . H3 H 0.6927 0.113 1.2061 0.031 Uiso 1 1 calc R . . C4 C 0.5799(4) 0.2287(3) 1.09423(18) 0.0229(6) Uani 1 1 d . . . H4 H 0.4767 0.2472 1.1206 0.027 Uiso 1 1 calc R . . C5 C 0.6063(3) 0.2798(3) 1.00467(18) 0.0180(6) Uani 1 1 d . . . C6 C 0.4786(3) 0.3647(3) 0.94396(18) 0.0196(6) Uani 1 1 d . . . C7 C 0.3266(4) 0.4130(3) 0.97031(19) 0.0269(7) Uani 1 1 d . . . H7 H 0.2932 0.3872 1.0304 0.032 Uiso 1 1 calc R . . C8 C 0.2250(4) 0.4992(3) 0.9075(2) 0.0284(7) Uani 1 1 d . . . H8 H 0.1209 0.5336 0.9244 0.034 Uiso 1 1 calc R . . C9 C 0.2744(4) 0.5354(3) 0.81998(19) 0.0248(6) Uani 1 1 d . . . H9 H 0.2062 0.5954 0.7764 0.03 Uiso 1 1 calc R . . C10 C 0.4258(3) 0.4821(3) 0.79759(18) 0.0197(6) Uani 1 1 d . . . C11 C 0.4891(3) 0.5162(3) 0.70649(18) 0.0179(6) Uani 1 1 d . . . C12 C 0.6288(3) 0.5043(2) 0.58992(17) 0.0177(6) Uani 1 1 d . . . C13 C 0.7412(3) 0.4624(3) 0.52734(18) 0.0178(6) Uani 1 1 d . . . C14 C 0.7665(4) 0.5462(3) 0.44440(18) 0.0217(6) Uani 1 1 d . . . H14 H 0.7093 0.6281 0.4275 0.026 Uiso 1 1 calc R . . C15 C 0.8773(4) 0.5070(3) 0.38715(18) 0.0244(7) Uani 1 1 d . . . H15 H 0.8955 0.5618 0.3299 0.029 Uiso 1 1 calc R . . C16 C 0.9606(4) 0.3886(3) 0.41341(18) 0.0224(6) Uani 1 1 d . . . H16 H 1.037 0.3611 0.3747 0.027 Uiso 1 1 calc R . . C17 C 0.9317(3) 0.3097(3) 0.49746(18) 0.0185(6) Uani 1 1 d . . . C18 C 1.0180(3) 0.1830(3) 0.53285(18) 0.0193(6) Uani 1 1 d . . . C19 C 1.1522(4) 0.1351(3) 0.49165(19) 0.0232(6) Uani 1 1 d . . . H19 H 1.1946 0.1845 0.4374 0.028 Uiso 1 1 calc R . . C20 C 1.2228(4) 0.0146(3) 0.5307(2) 0.0265(7) Uani 1 1 d . . . H20 H 1.3145 -0.0199 0.5034 0.032 Uiso 1 1 calc R . . C21 C 1.1593(4) -0.0562(3) 0.60995(19) 0.0252(7) Uani 1 1 d . . . H21 H 1.2053 -0.1399 0.6374 0.03 Uiso 1 1 calc R . . C22 C 1.0273(4) -0.0016(3) 0.64798(19) 0.0221(6) Uani 1 1 d . . . H22 H 0.9847 -0.0489 0.7029 0.027 Uiso 1 1 calc R . . C23 C 1.0980(4) 0.2095(3) 0.78774(18) 0.0196(6) Uani 1 1 d . . . C24 C 0.7104(3) 0.0196(3) 0.83433(19) 0.0204(6) Uani 1 1 d . . . C25 C 0.8423(3) 0.5972(3) 0.78991(17) 0.0184(6) 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 0.01508(17) 0.01794(18) 0.01620(17) -0.00459(13) -0.00032(13) -0.00007(14) Cu2 0.01798(18) 0.01588(18) 0.01537(17) -0.00379(13) 0.00124(13) -0.00163(14) S1 0.0188(4) 0.0253(4) 0.0468(5) -0.0106(4) 0.0085(3) -0.0035(3) S2 0.0377(5) 0.0373(5) 0.0216(4) -0.0091(3) 0.0055(3) -0.0144(4) S3 0.0326(4) 0.0218(4) 0.0488(5) -0.0159(4) 0.0051(4) -0.0047(3) O1 0.0219(11) 0.0247(12) 0.0251(11) -0.0041(9) -0.0054(9) -0.0049(9) O2 0.0326(14) 0.0440(15) 0.0405(14) -0.0074(12) -0.0063(11) -0.0023(12) N1 0.0194(12) 0.0193(12) 0.0175(12) -0.0060(10) -0.0020(9) -0.0034(10) N2 0.0172(12) 0.0153(12) 0.0176(11) -0.0054(9) -0.0002(9) -0.0027(9) N3 0.0164(12) 0.0152(12) 0.0174(11) -0.0047(9) -0.0031(9) -0.0008(9) N4 0.0180(12) 0.0137(11) 0.0161(11) -0.0021(9) 0.0014(9) -0.0021(10) N5 0.0156(11) 0.0186(12) 0.0167(11) -0.0053(9) -0.0024(9) -0.0038(10) N6 0.0175(12) 0.0210(13) 0.0176(12) -0.0051(10) -0.0012(9) -0.0041(10) N7 0.0245(13) 0.0228(13) 0.0185(12) -0.0048(10) -0.0024(10) 0.0010(11) N8 0.0255(13) 0.0194(13) 0.0189(12) -0.0030(10) -0.0039(10) 0.0014(10) N9 0.0177(13) 0.0223(13) 0.0237(13) -0.0039(10) 0.0003(10) -0.0001(10) N10 0.0276(14) 0.0179(13) 0.0239(14) -0.0032(10) 0.0031(11) -0.0028(11) N11 0.0276(14) 0.0228(14) 0.0353(15) -0.0096(12) 0.0039(11) -0.0077(11) C1 0.0210(15) 0.0252(16) 0.0218(15) -0.0072(12) -0.0017(12) -0.0019(12) C2 0.0287(16) 0.0209(15) 0.0214(15) -0.0048(12) -0.0079(12) -0.0005(13) C3 0.0350(18) 0.0277(17) 0.0155(14) -0.0047(12) -0.0013(12) -0.0097(14) C4 0.0254(16) 0.0237(15) 0.0199(14) -0.0067(12) 0.0002(12) -0.0039(13) C5 0.0200(14) 0.0165(14) 0.0194(14) -0.0074(11) -0.0024(11) -0.0042(11) C6 0.0210(15) 0.0197(15) 0.0193(14) -0.0072(12) -0.0008(11) -0.0041(12) C7 0.0259(16) 0.0337(18) 0.0202(15) -0.0076(13) 0.0045(12) -0.0025(14) C8 0.0212(16) 0.0379(19) 0.0264(16) -0.0135(14) 0.0026(13) 0.0049(14) C9 0.0223(15) 0.0247(16) 0.0256(15) -0.0075(13) -0.0047(12) 0.0055(13) C10 0.0203(14) 0.0175(14) 0.0218(14) -0.0071(11) -0.0020(11) -0.0006(12) C11 0.0164(14) 0.0179(14) 0.0194(14) -0.0058(11) -0.0045(11) 0.0004(11) C12 0.0189(14) 0.0165(14) 0.0165(13) -0.0019(11) -0.0065(11) -0.0032(11) C13 0.0167(14) 0.0190(14) 0.0193(14) -0.0070(11) -0.0033(11) -0.0046(11) C14 0.0252(15) 0.0186(15) 0.0196(14) -0.0018(11) -0.0031(12) -0.0060(12) C15 0.0288(16) 0.0318(17) 0.0132(14) -0.0047(12) 0.0029(12) -0.0124(14) C16 0.0231(15) 0.0267(16) 0.0191(14) -0.0082(12) 0.0012(12) -0.0068(13) C17 0.0156(14) 0.0233(15) 0.0194(14) -0.0088(12) 0.0009(11) -0.0068(12) C18 0.0174(14) 0.0236(15) 0.0201(14) -0.0095(12) -0.0018(11) -0.0062(12) C19 0.0212(15) 0.0288(16) 0.0213(14) -0.0108(13) 0.0022(12) -0.0023(13) C20 0.0212(15) 0.0337(18) 0.0312(17) -0.0202(14) -0.0014(13) -0.0009(13) C21 0.0244(16) 0.0257(16) 0.0278(16) -0.0119(13) -0.0078(13) 0.0013(13) C22 0.0231(15) 0.0230(15) 0.0209(14) -0.0068(12) -0.0039(12) -0.0034(12) C23 0.0203(16) 0.0161(14) 0.0208(14) -0.0027(11) -0.0019(12) -0.0035(12) C24 0.0180(14) 0.0149(14) 0.0287(16) -0.0075(12) 0.0013(12) -0.0015(11) C25 0.0164(14) 0.0231(16) 0.0137(13) -0.0030(11) 0.0025(11) -0.0027(12) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 N9 1.952(2) . ? Cu1 N1 2.009(2) . ? Cu1 N2 2.021(2) . ? Cu1 N4 2.046(2) . ? Cu1 N11 2.158(3) . ? Cu2 N4 1.950(2) . ? Cu2 N10 1.955(2) . ? Cu2 N6 1.981(2) . ? Cu2 N5 2.017(2) . ? Cu2 O1 2.348(2) . ? S1 C23 1.636(3) . ? S2 C24 1.613(3) . ? S3 C25 1.633(3) . ? O1 H1AO 0.874(18) . ? O1 H1BO 0.871(18) . ? O2 H2AO 0.914(19) . ? O2 H2BO 0.905(19) . ? N1 C1 1.338(4) . ? N1 C5 1.349(4) . ? N2 C6 1.345(3) . ? N2 C10 1.351(4) . ? N3 C11 1.359(4) . ? N3 C12 1.363(3) . ? N3 N4 1.417(3) . ? N4 H4N 0.895(18) . ? N5 C13 1.343(4) . ? N5 C17 1.357(4) . ? N6 C22 1.336(4) . ? N6 C18 1.351(3) . ? N7 C11 1.322(4) . ? N7 N8 1.379(3) . ? N8 C12 1.329(4) . ? N9 C23 1.161(4) . ? N10 C24 1.171(4) . ? N11 C25 1.151(4) . ? C1 C2 1.387(4) . ? C1 H1 0.95 . ? C2 C3 1.375(4) . ? C2 H2 0.95 . ? C3 C4 1.387(4) . ? C3 H3 0.95 . ? C4 C5 1.384(4) . ? C4 H4 0.95 . ? C5 C6 1.485(4) . ? C6 C7 1.389(4) . ? C7 C8 1.382(4) . ? C7 H7 0.95 . ? C8 C9 1.384(4) . ? C8 H8 0.95 . ? C9 C10 1.385(4) . ? C9 H9 0.95 . ? C10 C11 1.470(4) . ? C12 C13 1.471(4) . ? C13 C14 1.394(4) . ? C14 C15 1.387(4) . ? C14 H14 0.95 . ? C15 C16 1.375(4) . ? C15 H15 0.95 . ? C16 C17 1.392(4) . ? C16 H16 0.95 . ? C17 C18 1.470(4) . ? C18 C19 1.388(4) . ? C19 C20 1.378(4) . ? C19 H19 0.95 . ? C20 C21 1.387(4) . ? C20 H20 0.95 . ? C21 C22 1.383(4) . ? C21 H21 0.95 . ? C22 H22 0.95 . ? 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 N9 Cu1 N1 97.54(10) . . ? N9 Cu1 N2 177.22(9) . . ? N1 Cu1 N2 80.15(9) . . ? N9 Cu1 N4 95.34(10) . . ? N1 Cu1 N4 146.40(9) . . ? N2 Cu1 N4 85.85(9) . . ? N9 Cu1 N11 93.39(10) . . ? N1 Cu1 N11 111.68(10) . . ? N2 Cu1 N11 88.92(9) . . ? N4 Cu1 N11 98.32(9) . . ? N4 Cu2 N10 89.63(10) . . ? N4 Cu2 N6 162.82(10) . . ? N10 Cu2 N6 94.99(10) . . ? N4 Cu2 N5 94.52(9) . . ? N10 Cu2 N5 175.28(10) . . ? N6 Cu2 N5 81.69(9) . . ? N4 Cu2 O1 99.98(9) . . ? N10 Cu2 O1 90.71(9) . . ? N6 Cu2 O1 96.50(8) . . ? N5 Cu2 O1 86.34(8) . . ? Cu2 O1 H1AO 133(2) . . ? Cu2 O1 H1BO 120(2) . . ? H1AO O1 H1BO 106(3) . . ? H2AO O2 H2BO 104(4) . . ? C1 N1 C5 119.0(2) . . ? C1 N1 Cu1 125.17(19) . . ? C5 N1 Cu1 114.99(18) . . ? C6 N2 C10 119.7(2) . . ? C6 N2 Cu1 115.42(18) . . ? C10 N2 Cu1 124.85(18) . . ? C11 N3 C12 105.6(2) . . ? C11 N3 N4 124.8(2) . . ? C12 N3 N4 129.3(2) . . ? N3 N4 Cu2 119.59(16) . . ? N3 N4 Cu1 106.58(15) . . ? Cu2 N4 Cu1 115.23(11) . . ? N3 N4 H4N 102.4(19) . . ? Cu2 N4 H4N 106.4(19) . . ? Cu1 N4 H4N 105.0(19) . . ? C13 N5 C17 119.0(2) . . ? C13 N5 Cu2 127.62(19) . . ? C17 N5 Cu2 112.72(18) . . ? C22 N6 C18 119.0(2) . . ? C22 N6 Cu2 126.12(19) . . ? C18 N6 Cu2 114.88(19) . . ? C11 N7 N8 106.7(2) . . ? C12 N8 N7 107.9(2) . . ? C23 N9 Cu1 163.7(2) . . ? C24 N10 Cu2 143.6(2) . . ? C25 N11 Cu1 149.9(2) . . ? N1 C1 C2 122.0(3) . . ? N1 C1 H1 119 . . ? C2 C1 H1 119 . . ? C3 C2 C1 118.9(3) . . ? C3 C2 H2 120.6 . . ? C1 C2 H2 120.6 . . ? C2 C3 C4 119.7(3) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C5 C4 C3 118.4(3) . . ? C5 C4 H4 120.8 . . ? C3 C4 H4 120.8 . . ? N1 C5 C4 122.0(3) . . ? N1 C5 C6 114.7(2) . . ? C4 C5 C6 123.3(3) . . ? N2 C6 C7 121.2(3) . . ? N2 C6 C5 113.9(2) . . ? C7 C6 C5 124.8(3) . . ? C8 C7 C6 118.8(3) . . ? C8 C7 H7 120.6 . . ? C6 C7 H7 120.6 . . ? C7 C8 C9 120.1(3) . . ? C7 C8 H8 119.9 . . ? C9 C8 H8 119.9 . . ? C8 C9 C10 118.3(3) . . ? C8 C9 H9 120.8 . . ? C10 C9 H9 120.8 . . ? N2 C10 C9 121.8(3) . . ? N2 C10 C11 116.2(2) . . ? C9 C10 C11 122.0(3) . . ? N7 C11 N3 110.5(2) . . ? N7 C11 C10 126.0(3) . . ? N3 C11 C10 123.4(2) . . ? N8 C12 N3 109.3(2) . . ? N8 C12 C13 123.4(2) . . ? N3 C12 C13 127.2(2) . . ? N5 C13 C14 122.2(3) . . ? N5 C13 C12 118.9(2) . . ? C14 C13 C12 118.9(3) . . ? C15 C14 C13 118.3(3) . . ? C15 C14 H14 120.8 . . ? C13 C14 H14 120.8 . . ? C16 C15 C14 119.9(3) . . ? C16 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? C15 C16 C17 119.2(3) . . ? C15 C16 H16 120.4 . . ? C17 C16 H16 120.4 . . ? N5 C17 C16 121.4(3) . . ? N5 C17 C18 115.2(2) . . ? C16 C17 C18 123.4(3) . . ? N6 C18 C19 121.5(3) . . ? N6 C18 C17 114.5(2) . . ? C19 C18 C17 123.9(3) . . ? C20 C19 C18 118.9(3) . . ? C20 C19 H19 120.5 . . ? C18 C19 H19 120.5 . . ? C19 C20 C21 119.7(3) . . ? C19 C20 H20 120.1 . . ? C21 C20 H20 120.1 . . ? C22 C21 C20 118.2(3) . . ? C22 C21 H21 120.9 . . ? C20 C21 H21 120.9 . . ? N6 C22 C21 122.6(3) . . ? N6 C22 H22 118.7 . . ? C21 C22 H22 118.7 . . ? N9 C23 S1 178.0(3) . . ? N10 C24 S2 179.2(3) . . ? N11 C25 S3 179.3(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 O1 H1AO N8 0.874(18) 2.07(2) 2.891(3) 156(3) 2_666 O1 H1BO O2 0.871(18) 2.27(2) 3.021(3) 144(3) 1_545 O2 H2AO N7 0.914(19) 2.31(2) 3.198(4) 165(3) . O2 H2BO S3 0.905(19) 2.65(3) 3.448(3) 148(3) . O2 H2BO N10 0.905(19) 2.66(3) 3.297(4) 128(3) 1_565 N4 H4N S1 0.895(18) 2.566(19) 3.438(2) 165(3) 1_455 # END of CIF data_CDR19.2 _database_code_depnum_ccdc_archive 'CCDC 844324' #TrackingRef '7188_web_deposit_cif_file_0_MikkoM.Hanninen_ _audit_creation_date 2010-12-03T09:50:05-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C26 H18 Cu2 F6 N12 O6 S2' _chemical_formula_sum 'C26 H18 Cu2 F6 N12 O6 S2' _chemical_formula_weight 899.72 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-p 2ybc' _symmetry_Int_Tables_number 14 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 15.2701(7) _cell_length_b 12.6225(7) _cell_length_c 18.4419(8) _cell_angle_alpha 90 _cell_angle_beta 114.855(3) _cell_angle_gamma 90 _cell_volume 3225.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5940 _cell_measurement_theta_min 0.407 _cell_measurement_theta_max 28.283 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 1.853 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1800 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 1.547 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 2008)' _exptl_absorpt_correction_T_min 0.480 _exptl_absorpt_correction_T_max 0.746 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(2) _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_radiation_probe x-ray _diffrn_radiation_wavelength 0.71073 _diffrn_source 'Enraf Nonius FR590' _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0671 _diffrn_reflns_av_unetI/netI 0.0937 _diffrn_reflns_number 14588 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.77 _diffrn_reflns_theta_max 26 _diffrn_reflns_theta_full 26 _diffrn_measured_fraction_theta_full 0.985 _diffrn_measured_fraction_theta_max 0.985 _reflns_number_total 6252 _reflns_number_gt 4368 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^ > 2\s(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^)+(0.0251P)^2^+12.2680P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 6252 _refine_ls_number_parameters 491 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0967 _refine_ls_R_factor_gt 0.0605 _refine_ls_wR_factor_ref 0.139 _refine_ls_wR_factor_gt 0.1228 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.607 _refine_diff_density_min -0.625 _refine_diff_density_rms 0.117 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.21858(4) 0.60755(5) 0.01400(4) 0.02251(18) Uani 1 1 d . . . Cu2 Cu 0.21909(4) 0.57075(5) -0.14388(4) 0.02301(18) Uani 1 1 d . . . S1 S 0.26305(10) 0.85821(11) -0.05440(8) 0.0234(3) Uani 1 1 d . . . S2 S 0.23628(10) 0.34848(12) 0.12567(9) 0.0306(3) Uani 1 1 d . . . F1 F 0.3806(3) 0.9948(3) 0.0450(2) 0.0631(12) Uani 1 1 d . . . F2 F 0.4497(3) 0.8569(3) 0.0284(3) 0.0755(15) Uani 1 1 d . . . F3 F 0.3988(3) 0.9761(3) -0.0620(2) 0.0511(10) Uani 1 1 d . . . F4 F 0.1578(3) 0.1788(3) 0.0432(3) 0.0740(14) Uani 1 1 d . . . F5 F 0.2290(4) 0.1548(4) 0.1704(3) 0.0974(18) Uani 1 1 d . . . F6 F 0.3116(4) 0.1750(4) 0.1025(3) 0.0987(19) Uani 1 1 d . . . O1 O 0.2568(3) 0.8025(3) 0.0121(2) 0.0366(10) Uani 1 1 d . . . O2 O 0.2741(3) 0.7881(3) -0.1118(2) 0.0296(9) Uani 1 1 d . . . O3 O 0.1970(3) 0.9439(3) -0.0879(3) 0.0472(12) Uani 1 1 d . . . O4 O 0.2417(4) 0.3916(4) 0.0559(3) 0.0527(13) Uani 1 1 d . . . O5 O 0.3220(3) 0.3624(4) 0.1983(3) 0.0464(11) Uani 1 1 d . . . O6 O 0.1473(3) 0.3697(4) 0.1309(3) 0.0495(12) Uani 1 1 d . . . N1 N 0.1379(3) 0.6242(3) 0.0732(2) 0.0234(10) Uani 1 1 d . . . N2 N 0.1196(3) 0.6070(4) -0.1007(2) 0.0234(10) Uani 1 1 d . . . N3 N 0.0679(4) 0.6853(4) -0.1289(3) 0.0342(12) Uani 1 1 d . . . N4 N 0.0175(4) 0.7561(5) -0.1570(4) 0.0520(15) Uani 1 1 d . . . N12 N 0.3256(3) 0.6193(3) 0.1229(2) 0.0199(9) Uani 1 1 d . . . N14 N 0.5398(3) 0.6477(4) 0.0845(3) 0.0247(10) Uani 1 1 d . . . N15 N 0.5394(3) 0.6434(3) 0.0097(3) 0.0237(10) Uani 1 1 d . . . N17 N 0.3956(3) 0.5969(3) -0.0018(2) 0.0204(9) Uani 1 1 d . . . N18 N 0.3034(3) 0.5515(3) -0.0316(2) 0.0192(9) Uani 1 1 d D . . H18 H 0.312(4) 0.4801(17) -0.024(3) 0.023 Uiso 1 1 d D . . N24 N 0.3270(3) 0.5961(3) -0.1765(2) 0.0194(9) Uani 1 1 d . . . N30 N 0.1398(3) 0.5826(3) -0.2599(2) 0.0240(10) Uani 1 1 d . . . N33 N 0.2002(4) 0.3876(4) -0.1540(3) 0.0330(11) Uani 1 1 d . . . C2 C 0.0413(4) 0.6239(4) 0.0422(3) 0.0260(12) Uani 1 1 d . . . H2 H 0.006 0.6216 -0.0142 0.031 Uiso 1 1 calc R . . C3 C -0.0085(4) 0.6268(4) 0.0893(3) 0.0288(13) Uani 1 1 d . . . H3 H -0.077 0.6268 0.0658 0.035 Uiso 1 1 calc R . . C4 C 0.0431(4) 0.6297(5) 0.1717(3) 0.0326(14) Uani 1 1 d . . . H4 H 0.0103 0.6321 0.2055 0.039 Uiso 1 1 calc R . . C5 C 0.1424(4) 0.6291(4) 0.2041(3) 0.0286(13) Uani 1 1 d . . . H5 H 0.1787 0.6317 0.2604 0.034 Uiso 1 1 calc R . . C6 C 0.1891(4) 0.6248(4) 0.1538(3) 0.0208(11) Uani 1 1 d . . . C7 C 0.2952(4) 0.6229(4) 0.1816(3) 0.0242(12) Uani 1 1 d . . . C8 C 0.3602(4) 0.6242(4) 0.2612(3) 0.0257(12) Uani 1 1 d . . . H8 H 0.3378 0.6244 0.3021 0.031 Uiso 1 1 calc R . . C9 C 0.4578(4) 0.6252(4) 0.2806(3) 0.0287(13) Uani 1 1 d . . . H9 H 0.5031 0.6253 0.335 0.034 Uiso 1 1 calc R . . C10 C 0.4894(4) 0.6261(4) 0.2203(3) 0.0260(12) Uani 1 1 d . . . H10 H 0.5564 0.6294 0.2326 0.031 Uiso 1 1 calc R . . C11 C 0.4211(4) 0.6222(4) 0.1416(3) 0.0193(11) Uani 1 1 d . . . C13 C 0.4528(4) 0.6216(4) 0.0763(3) 0.0205(11) Uani 1 1 d . . . C16 C 0.4521(4) 0.6141(4) -0.0413(3) 0.0187(11) Uani 1 1 d . . . C19 C 0.4211(4) 0.6079(4) -0.1289(3) 0.0180(10) Uani 1 1 d . . . C20 C 0.4896(4) 0.6209(4) -0.1592(3) 0.0222(11) Uani 1 1 d . . . H20 H 0.5559 0.6294 -0.1246 0.027 Uiso 1 1 calc R . . C21 C 0.4587(4) 0.6212(4) -0.2414(3) 0.0256(12) Uani 1 1 d . . . H21 H 0.5043 0.6273 -0.2637 0.031 Uiso 1 1 calc R . . C22 C 0.3618(4) 0.6126(4) -0.2906(3) 0.0237(12) Uani 1 1 d . . . H22 H 0.3397 0.6147 -0.3471 0.028 Uiso 1 1 calc R . . C23 C 0.2973(4) 0.6008(4) -0.2567(3) 0.0192(11) Uani 1 1 d . . . C25 C 0.1919(4) 0.5952(4) -0.3034(3) 0.0198(11) Uani 1 1 d . . . C26 C 0.1466(4) 0.6024(4) -0.3857(3) 0.0250(12) Uani 1 1 d . . . H26 H 0.1835 0.6116 -0.4158 0.03 Uiso 1 1 calc R . . C27 C 0.0469(4) 0.5961(5) -0.4240(3) 0.0309(13) Uani 1 1 d . . . H27 H 0.0147 0.6039 -0.4804 0.037 Uiso 1 1 calc R . . C28 C -0.0057(4) 0.5782(5) -0.3792(3) 0.0338(14) Uani 1 1 d . . . H28 H -0.0737 0.5691 -0.4045 0.041 Uiso 1 1 calc R . . C29 C 0.0433(4) 0.5740(5) -0.2974(3) 0.0297(13) Uani 1 1 d . . . H29 H 0.0077 0.5646 -0.2663 0.036 Uiso 1 1 calc R . . C31 C 0.3797(4) 0.9250(4) -0.0081(3) 0.0297(13) Uani 1 1 d . . . C32 C 0.2332(5) 0.2064(5) 0.1090(4) 0.0497(18) Uani 1 1 d . . . C34 C 0.2238(4) 0.3024(5) -0.1527(3) 0.0320(14) Uani 1 1 d . . . C35 C 0.2560(6) 0.1939(5) -0.1488(5) 0.059(2) Uani 1 1 d . . . H35A H 0.3266 0.1923 -0.1278 0.089 Uiso 1 1 calc R . . H35B H 0.2279 0.1628 -0.2024 0.089 Uiso 1 1 calc R . . H35C H 0.2355 0.1531 -0.1135 0.089 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 0.0214(3) 0.0324(4) 0.0155(3) -0.0019(3) 0.0094(3) -0.0022(3) Cu2 0.0210(3) 0.0339(4) 0.0159(3) 0.0020(3) 0.0095(3) -0.0019(3) S1 0.0272(7) 0.0218(7) 0.0246(7) 0.0011(6) 0.0142(6) 0.0008(6) S2 0.0287(8) 0.0293(8) 0.0329(8) 0.0015(6) 0.0120(7) -0.0061(6) F1 0.092(3) 0.055(3) 0.051(2) -0.033(2) 0.038(2) -0.034(2) F2 0.036(2) 0.038(2) 0.116(4) 0.013(2) -0.004(2) 0.0013(19) F3 0.060(3) 0.060(3) 0.042(2) -0.0034(19) 0.030(2) -0.031(2) F4 0.064(3) 0.049(3) 0.070(3) -0.022(2) -0.009(2) -0.016(2) F5 0.146(5) 0.044(3) 0.085(4) 0.025(3) 0.032(4) -0.015(3) F6 0.069(3) 0.095(4) 0.111(4) -0.041(3) 0.017(3) 0.034(3) O1 0.060(3) 0.033(2) 0.030(2) -0.0029(18) 0.032(2) -0.011(2) O2 0.046(2) 0.027(2) 0.0235(19) -0.0045(17) 0.0221(19) -0.0042(18) O3 0.040(3) 0.035(3) 0.066(3) 0.008(2) 0.022(2) 0.011(2) O4 0.074(3) 0.050(3) 0.042(3) 0.003(2) 0.032(3) -0.019(3) O5 0.031(2) 0.059(3) 0.043(3) -0.005(2) 0.009(2) -0.012(2) O6 0.031(2) 0.059(3) 0.056(3) 0.006(2) 0.016(2) 0.007(2) N1 0.025(2) 0.027(3) 0.019(2) 0.0006(19) 0.010(2) -0.002(2) N2 0.025(2) 0.029(3) 0.020(2) 0.001(2) 0.013(2) 0.002(2) N3 0.029(3) 0.047(3) 0.032(3) 0.006(3) 0.019(2) -0.001(3) N4 0.043(3) 0.052(4) 0.067(4) 0.020(3) 0.030(3) 0.013(3) N12 0.024(2) 0.020(2) 0.016(2) -0.0014(18) 0.0090(19) 0.0018(19) N14 0.020(2) 0.033(3) 0.022(2) -0.002(2) 0.010(2) 0.001(2) N15 0.019(2) 0.027(3) 0.026(2) -0.002(2) 0.010(2) -0.0003(19) N17 0.017(2) 0.025(2) 0.019(2) -0.0002(19) 0.0072(18) 0.0004(19) N18 0.021(2) 0.017(2) 0.020(2) -0.0010(19) 0.0100(19) -0.0016(19) N24 0.025(2) 0.017(2) 0.018(2) 0.0028(18) 0.0111(19) 0.0028(18) N30 0.028(3) 0.028(3) 0.018(2) 0.0001(19) 0.012(2) -0.001(2) N33 0.038(3) 0.030(3) 0.030(3) 0.000(2) 0.014(2) -0.002(2) C2 0.028(3) 0.024(3) 0.028(3) 0.000(2) 0.014(3) -0.005(2) C3 0.027(3) 0.027(3) 0.034(3) -0.002(3) 0.014(3) 0.000(2) C4 0.043(4) 0.038(4) 0.029(3) -0.002(3) 0.027(3) -0.006(3) C5 0.038(3) 0.031(3) 0.019(3) -0.003(2) 0.014(3) -0.002(3) C6 0.034(3) 0.013(3) 0.021(3) -0.002(2) 0.016(2) -0.001(2) C7 0.032(3) 0.018(3) 0.023(3) -0.006(2) 0.012(2) -0.003(2) C8 0.040(3) 0.021(3) 0.018(3) -0.002(2) 0.014(3) 0.001(3) C9 0.038(3) 0.028(3) 0.013(2) 0.000(2) 0.004(2) 0.008(3) C10 0.026(3) 0.029(3) 0.018(3) -0.001(2) 0.004(2) 0.003(2) C11 0.024(3) 0.014(3) 0.022(3) 0.000(2) 0.012(2) 0.002(2) C13 0.020(3) 0.022(3) 0.015(2) 0.000(2) 0.004(2) 0.001(2) C16 0.022(3) 0.018(3) 0.021(3) 0.004(2) 0.013(2) 0.004(2) C19 0.024(3) 0.014(3) 0.016(2) 0.001(2) 0.008(2) 0.004(2) C20 0.025(3) 0.022(3) 0.021(3) 0.001(2) 0.012(2) 0.001(2) C21 0.033(3) 0.022(3) 0.032(3) 0.001(2) 0.024(3) 0.001(2) C22 0.034(3) 0.021(3) 0.020(3) 0.000(2) 0.015(2) 0.001(2) C23 0.027(3) 0.014(3) 0.017(2) 0.000(2) 0.010(2) 0.001(2) C25 0.026(3) 0.014(3) 0.021(3) -0.005(2) 0.011(2) -0.005(2) C26 0.032(3) 0.025(3) 0.019(3) 0.001(2) 0.012(2) -0.004(2) C27 0.036(3) 0.035(3) 0.021(3) 0.000(3) 0.012(3) -0.003(3) C28 0.026(3) 0.047(4) 0.022(3) 0.010(3) 0.003(2) -0.002(3) C29 0.027(3) 0.036(3) 0.024(3) 0.004(3) 0.008(2) 0.000(3) C31 0.045(4) 0.017(3) 0.031(3) 0.000(2) 0.021(3) 0.000(3) C32 0.044(4) 0.036(4) 0.053(4) -0.005(3) 0.004(4) 0.000(3) C34 0.036(3) 0.034(4) 0.029(3) 0.003(3) 0.016(3) -0.004(3) C35 0.073(5) 0.036(4) 0.084(6) 0.009(4) 0.049(5) 0.003(4) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 N18 1.949(4) . ? Cu1 N1 1.971(4) . ? Cu1 N12 1.992(4) . ? Cu1 N2 2.018(4) . ? Cu1 Cu2 2.9515(8) . ? Cu2 N18 1.941(4) . ? Cu2 N30 1.972(4) . ? Cu2 N24 2.004(4) . ? Cu2 N2 2.042(4) . ? Cu2 N33 2.327(5) . ? S1 O3 1.430(4) . ? S1 O2 1.443(4) . ? S1 O1 1.452(4) . ? S1 C31 1.826(6) . ? S2 O6 1.427(4) . ? S2 O4 1.432(4) . ? S2 O5 1.437(4) . ? S2 C32 1.817(7) . ? F1 C31 1.313(6) . ? F2 C31 1.315(7) . ? F3 C31 1.317(6) . ? F4 C32 1.322(7) . ? F5 C32 1.330(8) . ? F6 C32 1.314(8) . ? N1 C2 1.339(7) . ? N1 C6 1.358(6) . ? N2 N3 1.235(7) . ? N3 N4 1.151(7) . ? N12 C7 1.346(6) . ? N12 C11 1.351(6) . ? N14 C13 1.314(6) . ? N14 N15 1.377(6) . ? N15 C16 1.320(6) . ? N17 C16 1.361(6) . ? N17 C13 1.370(6) . ? N17 N18 1.400(6) . ? N18 H18 0.911(19) . ? N24 C19 1.341(6) . ? N24 C23 1.354(6) . ? N30 C29 1.343(7) . ? N30 C25 1.356(6) . ? N33 C34 1.131(7) . ? C2 C3 1.375(7) . ? C2 H2 0.95 . ? C3 C4 1.388(8) . ? C3 H3 0.95 . ? C4 C5 1.376(8) . ? C4 H4 0.95 . ? C5 C6 1.389(7) . ? C5 H5 0.95 . ? C6 C7 1.480(7) . ? C7 C8 1.385(7) . ? C8 C9 1.379(8) . ? C8 H8 0.95 . ? C9 C10 1.387(7) . ? C9 H9 0.95 . ? C10 C11 1.387(7) . ? C10 H10 0.95 . ? C11 C13 1.473(7) . ? C16 C19 1.483(6) . ? C19 C20 1.388(7) . ? C20 C21 1.384(7) . ? C20 H20 0.95 . ? C21 C22 1.377(7) . ? C21 H21 0.95 . ? C22 C23 1.379(7) . ? C22 H22 0.95 . ? C23 C25 1.474(7) . ? C25 C26 1.382(7) . ? C26 C27 1.386(8) . ? C26 H26 0.95 . ? C27 C28 1.390(7) . ? C27 H27 0.95 . ? C28 C29 1.375(7) . ? C28 H28 0.95 . ? C29 H29 0.95 . ? C34 C35 1.447(9) . ? C35 H35A 0.98 . ? C35 H35B 0.98 . ? C35 H35C 0.98 . ? 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 N18 Cu1 N1 163.94(18) . . ? N18 Cu1 N12 92.81(17) . . ? N1 Cu1 N12 82.69(17) . . ? N18 Cu1 N2 83.55(17) . . ? N1 Cu1 N2 102.34(17) . . ? N12 Cu1 N2 173.18(17) . . ? N18 Cu1 Cu2 40.53(12) . . ? N1 Cu1 Cu2 145.55(13) . . ? N12 Cu1 Cu2 131.68(12) . . ? N2 Cu1 Cu2 43.68(12) . . ? N18 Cu2 N30 175.59(18) . . ? N18 Cu2 N24 94.59(17) . . ? N30 Cu2 N24 82.50(17) . . ? N18 Cu2 N2 83.15(17) . . ? N30 Cu2 N2 100.82(17) . . ? N24 Cu2 N2 157.26(18) . . ? N18 Cu2 N33 88.02(17) . . ? N30 Cu2 N33 89.39(17) . . ? N24 Cu2 N33 102.94(17) . . ? N2 Cu2 N33 99.59(17) . . ? N18 Cu2 Cu1 40.75(12) . . ? N30 Cu2 Cu1 143.45(13) . . ? N24 Cu2 Cu1 127.94(12) . . ? N2 Cu2 Cu1 43.05(12) . . ? N33 Cu2 Cu1 100.60(12) . . ? O3 S1 O2 115.2(3) . . ? O3 S1 O1 116.5(3) . . ? O2 S1 O1 113.1(2) . . ? O3 S1 C31 103.0(3) . . ? O2 S1 C31 103.6(2) . . ? O1 S1 C31 103.1(2) . . ? O6 S2 O4 113.9(3) . . ? O6 S2 O5 115.8(3) . . ? O4 S2 O5 114.6(3) . . ? O6 S2 C32 103.8(3) . . ? O4 S2 C32 103.3(3) . . ? O5 S2 C32 103.1(3) . . ? C2 N1 C6 119.4(4) . . ? C2 N1 Cu1 126.6(4) . . ? C6 N1 Cu1 113.6(3) . . ? N3 N2 Cu1 120.2(4) . . ? N3 N2 Cu2 117.7(3) . . ? Cu1 N2 Cu2 93.27(18) . . ? N4 N3 N2 177.7(7) . . ? C7 N12 C11 119.6(4) . . ? C7 N12 Cu1 113.5(3) . . ? C11 N12 Cu1 126.8(3) . . ? C13 N14 N15 107.3(4) . . ? C16 N15 N14 107.6(4) . . ? C16 N17 C13 105.0(4) . . ? C16 N17 N18 127.9(4) . . ? C13 N17 N18 126.7(4) . . ? N17 N18 Cu2 118.3(3) . . ? N17 N18 Cu1 115.0(3) . . ? Cu2 N18 Cu1 98.71(19) . . ? N17 N18 H18 107(3) . . ? Cu2 N18 H18 106(3) . . ? Cu1 N18 H18 112(3) . . ? C19 N24 C23 119.1(4) . . ? C19 N24 Cu2 127.7(3) . . ? C23 N24 Cu2 113.2(3) . . ? C29 N30 C25 119.6(4) . . ? C29 N30 Cu2 126.4(3) . . ? C25 N30 Cu2 113.9(3) . . ? C34 N33 Cu2 156.3(5) . . ? N1 C2 C3 122.2(5) . . ? N1 C2 H2 118.9 . . ? C3 C2 H2 118.9 . . ? C2 C3 C4 118.8(5) . . ? C2 C3 H3 120.6 . . ? C4 C3 H3 120.6 . . ? C5 C4 C3 119.3(5) . . ? C5 C4 H4 120.3 . . ? C3 C4 H4 120.3 . . ? C4 C5 C6 119.5(5) . . ? C4 C5 H5 120.3 . . ? C6 C5 H5 120.3 . . ? N1 C6 C5 120.7(5) . . ? N1 C6 C7 115.0(4) . . ? C5 C6 C7 124.3(5) . . ? N12 C7 C8 121.2(5) . . ? N12 C7 C6 114.8(4) . . ? C8 C7 C6 124.0(5) . . ? C9 C8 C7 119.3(5) . . ? C9 C8 H8 120.4 . . ? C7 C8 H8 120.4 . . ? C8 C9 C10 119.7(5) . . ? C8 C9 H9 120.1 . . ? C10 C9 H9 120.1 . . ? C9 C10 C11 118.5(5) . . ? C9 C10 H10 120.8 . . ? C11 C10 H10 120.8 . . ? N12 C11 C10 121.6(5) . . ? N12 C11 C13 118.8(4) . . ? C10 C11 C13 119.6(5) . . ? N14 C13 N17 110.1(4) . . ? N14 C13 C11 124.6(4) . . ? N17 C13 C11 125.2(4) . . ? N15 C16 N17 109.9(4) . . ? N15 C16 C19 123.7(4) . . ? N17 C16 C19 126.3(4) . . ? N24 C19 C20 122.0(4) . . ? N24 C19 C16 118.9(4) . . ? C20 C19 C16 119.0(4) . . ? C21 C20 C19 118.3(5) . . ? C21 C20 H20 120.9 . . ? C19 C20 H20 120.9 . . ? C22 C21 C20 120.0(5) . . ? C22 C21 H21 120 . . ? C20 C21 H21 120 . . ? C21 C22 C23 118.9(5) . . ? C21 C22 H22 120.6 . . ? C23 C22 H22 120.6 . . ? N24 C23 C22 121.7(5) . . ? N24 C23 C25 114.7(4) . . ? C22 C23 C25 123.6(4) . . ? N30 C25 C26 120.7(5) . . ? N30 C25 C23 115.4(4) . . ? C26 C25 C23 123.9(5) . . ? C25 C26 C27 119.4(5) . . ? C25 C26 H26 120.3 . . ? C27 C26 H26 120.3 . . ? C26 C27 C28 119.4(5) . . ? C26 C27 H27 120.3 . . ? C28 C27 H27 120.3 . . ? C29 C28 C27 118.3(5) . . ? C29 C28 H28 120.9 . . ? C27 C28 H28 120.9 . . ? N30 C29 C28 122.4(5) . . ? N30 C29 H29 118.8 . . ? C28 C29 H29 118.8 . . ? F1 C31 F2 107.8(5) . . ? F1 C31 F3 107.3(5) . . ? F2 C31 F3 108.4(5) . . ? F1 C31 S1 111.2(4) . . ? F2 C31 S1 111.2(4) . . ? F3 C31 S1 110.8(4) . . ? F6 C32 F4 108.2(6) . . ? F6 C32 F5 107.6(6) . . ? F4 C32 F5 108.5(6) . . ? F6 C32 S2 110.7(5) . . ? F4 C32 S2 111.4(5) . . ? F5 C32 S2 110.3(5) . . ? N33 C34 C35 178.4(7) . . ? C34 C35 H35A 109.5 . . ? C34 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C34 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 Cu1 Cu2 N18 -155.4(3) . . . . ? N12 Cu1 Cu2 N18 19.9(2) . . . . ? N2 Cu1 Cu2 N18 -167.0(3) . . . . ? N18 Cu1 Cu2 N30 177.8(3) . . . . ? N1 Cu1 Cu2 N30 22.4(3) . . . . ? N12 Cu1 Cu2 N30 -162.3(3) . . . . ? N2 Cu1 Cu2 N30 10.8(3) . . . . ? N18 Cu1 Cu2 N24 -41.5(2) . . . . ? N1 Cu1 Cu2 N24 163.1(3) . . . . ? N12 Cu1 Cu2 N24 -21.6(2) . . . . ? N2 Cu1 Cu2 N24 151.5(2) . . . . ? N18 Cu1 Cu2 N2 167.0(3) . . . . ? N1 Cu1 Cu2 N2 11.7(3) . . . . ? N12 Cu1 Cu2 N2 -173.0(3) . . . . ? N18 Cu1 Cu2 N33 74.3(2) . . . . ? N1 Cu1 Cu2 N33 -81.1(3) . . . . ? N12 Cu1 Cu2 N33 94.2(2) . . . . ? N2 Cu1 Cu2 N33 -92.8(2) . . . . ? N18 Cu1 N1 C2 -104.2(7) . . . . ? N12 Cu1 N1 C2 -178.7(5) . . . . ? N2 Cu1 N1 C2 6.0(5) . . . . ? Cu2 Cu1 N1 C2 -2.2(6) . . . . ? N18 Cu1 N1 C6 68.6(8) . . . . ? N12 Cu1 N1 C6 -5.9(4) . . . . ? N2 Cu1 N1 C6 178.8(4) . . . . ? Cu2 Cu1 N1 C6 170.6(2) . . . . ? N18 Cu1 N2 N3 -133.3(4) . . . . ? N1 Cu1 N2 N3 61.9(4) . . . . ? N12 Cu1 N2 N3 -75.3(16) . . . . ? Cu2 Cu1 N2 N3 -124.9(5) . . . . ? N18 Cu1 N2 Cu2 -8.44(17) . . . . ? N1 Cu1 N2 Cu2 -173.28(17) . . . . ? N12 Cu1 N2 Cu2 49.6(15) . . . . ? N18 Cu2 N2 N3 135.3(4) . . . . ? N30 Cu2 N2 N3 -46.7(4) . . . . ? N24 Cu2 N2 N3 49.7(7) . . . . ? N33 Cu2 N2 N3 -137.9(4) . . . . ? Cu1 Cu2 N2 N3 126.8(5) . . . . ? N18 Cu2 N2 Cu1 8.48(18) . . . . ? N30 Cu2 N2 Cu1 -173.48(17) . . . . ? N24 Cu2 N2 Cu1 -77.0(5) . . . . ? N33 Cu2 N2 Cu1 95.29(18) . . . . ? Cu1 N2 N3 N4 -156(15) . . . . ? Cu2 N2 N3 N4 92(15) . . . . ? N18 Cu1 N12 C7 -159.1(4) . . . . ? N1 Cu1 N12 C7 5.4(4) . . . . ? N2 Cu1 N12 C7 143.3(14) . . . . ? Cu2 Cu1 N12 C7 -171.9(3) . . . . ? N18 Cu1 N12 C11 19.9(4) . . . . ? N1 Cu1 N12 C11 -175.6(4) . . . . ? N2 Cu1 N12 C11 -37.6(17) . . . . ? Cu2 Cu1 N12 C11 7.1(5) . . . . ? C13 N14 N15 C16 -0.4(6) . . . . ? C16 N17 N18 Cu2 -30.8(6) . . . . ? C13 N17 N18 Cu2 157.9(4) . . . . ? C16 N17 N18 Cu1 -146.9(4) . . . . ? C13 N17 N18 Cu1 41.8(6) . . . . ? N30 Cu2 N18 N17 72(2) . . . . ? N24 Cu2 N18 N17 23.8(3) . . . . ? N2 Cu2 N18 N17 -133.5(4) . . . . ? N33 Cu2 N18 N17 126.6(3) . . . . ? Cu1 Cu2 N18 N17 -124.6(4) . . . . ? N30 Cu2 N18 Cu1 -163(2) . . . . ? N24 Cu2 N18 Cu1 148.39(18) . . . . ? N2 Cu2 N18 Cu1 -8.87(18) . . . . ? N33 Cu2 N18 Cu1 -108.78(19) . . . . ? N1 Cu1 N18 N17 -111.5(6) . . . . ? N12 Cu1 N18 N17 -38.3(3) . . . . ? N2 Cu1 N18 N17 135.9(3) . . . . ? Cu2 Cu1 N18 N17 126.9(4) . . . . ? N1 Cu1 N18 Cu2 121.6(6) . . . . ? N12 Cu1 N18 Cu2 -165.24(18) . . . . ? N2 Cu1 N18 Cu2 8.97(18) . . . . ? N18 Cu2 N24 C19 -7.5(4) . . . . ? N30 Cu2 N24 C19 175.8(4) . . . . ? N2 Cu2 N24 C19 75.7(6) . . . . ? N33 Cu2 N24 C19 -96.6(4) . . . . ? Cu1 Cu2 N24 C19 18.2(5) . . . . ? N18 Cu2 N24 C23 172.2(3) . . . . ? N30 Cu2 N24 C23 -4.4(3) . . . . ? N2 Cu2 N24 C23 -104.5(5) . . . . ? N33 Cu2 N24 C23 83.2(4) . . . . ? Cu1 Cu2 N24 C23 -162.0(3) . . . . ? N18 Cu2 N30 C29 131(2) . . . . ? N24 Cu2 N30 C29 179.7(5) . . . . ? N2 Cu2 N30 C29 -23.1(5) . . . . ? N33 Cu2 N30 C29 76.5(5) . . . . ? Cu1 Cu2 N30 C29 -30.6(6) . . . . ? N18 Cu2 N30 C25 -46(3) . . . . ? N24 Cu2 N30 C25 3.3(3) . . . . ? N2 Cu2 N30 C25 160.5(3) . . . . ? N33 Cu2 N30 C25 -99.9(4) . . . . ? Cu1 Cu2 N30 C25 153.0(3) . . . . ? N18 Cu2 N33 C34 -64.6(11) . . . . ? N30 Cu2 N33 C34 111.8(11) . . . . ? N24 Cu2 N33 C34 29.6(12) . . . . ? N2 Cu2 N33 C34 -147.3(11) . . . . ? Cu1 Cu2 N33 C34 -103.6(11) . . . . ? C6 N1 C2 C3 1.7(8) . . . . ? Cu1 N1 C2 C3 174.1(4) . . . . ? N1 C2 C3 C4 -0.3(8) . . . . ? C2 C3 C4 C5 -0.3(9) . . . . ? C3 C4 C5 C6 -0.5(9) . . . . ? C2 N1 C6 C5 -2.5(7) . . . . ? Cu1 N1 C6 C5 -175.9(4) . . . . ? C2 N1 C6 C7 178.7(5) . . . . ? Cu1 N1 C6 C7 5.4(6) . . . . ? C4 C5 C6 N1 1.9(8) . . . . ? C4 C5 C6 C7 -179.4(5) . . . . ? C11 N12 C7 C8 -3.3(7) . . . . ? Cu1 N12 C7 C8 175.8(4) . . . . ? C11 N12 C7 C6 176.9(5) . . . . ? Cu1 N12 C7 C6 -4.0(5) . . . . ? N1 C6 C7 N12 -0.9(7) . . . . ? C5 C6 C7 N12 -179.6(5) . . . . ? N1 C6 C7 C8 179.3(5) . . . . ? C5 C6 C7 C8 0.6(8) . . . . ? N12 C7 C8 C9 2.1(8) . . . . ? C6 C7 C8 C9 -178.1(5) . . . . ? C7 C8 C9 C10 0.7(8) . . . . ? C8 C9 C10 C11 -2.3(8) . . . . ? C7 N12 C11 C10 1.7(7) . . . . ? Cu1 N12 C11 C10 -177.3(4) . . . . ? C7 N12 C11 C13 -178.1(4) . . . . ? Cu1 N12 C11 C13 2.9(7) . . . . ? C9 C10 C11 N12 1.1(8) . . . . ? C9 C10 C11 C13 -179.2(5) . . . . ? N15 N14 C13 N17 1.9(6) . . . . ? N15 N14 C13 C11 -176.4(4) . . . . ? C16 N17 C13 N14 -2.6(6) . . . . ? N18 N17 C13 N14 170.3(4) . . . . ? C16 N17 C13 C11 175.7(5) . . . . ? N18 N17 C13 C11 -11.4(8) . . . . ? N12 C11 C13 N14 164.0(5) . . . . ? C10 C11 C13 N14 -15.7(8) . . . . ? N12 C11 C13 N17 -14.0(7) . . . . ? C10 C11 C13 N17 166.3(5) . . . . ? N14 N15 C16 N17 -1.3(6) . . . . ? N14 N15 C16 C19 175.5(4) . . . . ? C13 N17 C16 N15 2.3(6) . . . . ? N18 N17 C16 N15 -170.5(4) . . . . ? C13 N17 C16 C19 -174.3(5) . . . . ? N18 N17 C16 C19 12.9(8) . . . . ? C23 N24 C19 C20 -2.4(7) . . . . ? Cu2 N24 C19 C20 177.4(4) . . . . ? C23 N24 C19 C16 173.5(4) . . . . ? Cu2 N24 C19 C16 -6.7(7) . . . . ? N15 C16 C19 N24 -168.1(5) . . . . ? N17 C16 C19 N24 8.1(8) . . . . ? N15 C16 C19 C20 8.0(8) . . . . ? N17 C16 C19 C20 -175.8(5) . . . . ? N24 C19 C20 C21 -0.2(8) . . . . ? C16 C19 C20 C21 -176.2(5) . . . . ? C19 C20 C21 C22 2.3(8) . . . . ? C20 C21 C22 C23 -1.8(8) . . . . ? C19 N24 C23 C22 3.0(7) . . . . ? Cu2 N24 C23 C22 -176.8(4) . . . . ? C19 N24 C23 C25 -175.5(4) . . . . ? Cu2 N24 C23 C25 4.7(5) . . . . ? C21 C22 C23 N24 -0.9(8) . . . . ? C21 C22 C23 C25 177.4(5) . . . . ? C29 N30 C25 C26 1.9(8) . . . . ? Cu2 N30 C25 C26 178.6(4) . . . . ? C29 N30 C25 C23 -178.3(5) . . . . ? Cu2 N30 C25 C23 -1.7(5) . . . . ? N24 C23 C25 N30 -2.1(6) . . . . ? C22 C23 C25 N30 179.4(5) . . . . ? N24 C23 C25 C26 177.6(5) . . . . ? C22 C23 C25 C26 -0.8(8) . . . . ? N30 C25 C26 C27 -0.3(8) . . . . ? C23 C25 C26 C27 180.0(5) . . . . ? C25 C26 C27 C28 -2.7(9) . . . . ? C26 C27 C28 C29 4.0(9) . . . . ? C25 N30 C29 C28 -0.5(8) . . . . ? Cu2 N30 C29 C28 -176.7(4) . . . . ? C27 C28 C29 N30 -2.5(9) . . . . ? O3 S1 C31 F1 57.9(5) . . . . ? O2 S1 C31 F1 178.2(4) . . . . ? O1 S1 C31 F1 -63.7(4) . . . . ? O3 S1 C31 F2 178.0(4) . . . . ? O2 S1 C31 F2 -61.6(5) . . . . ? O1 S1 C31 F2 56.5(5) . . . . ? O3 S1 C31 F3 -61.3(4) . . . . ? O2 S1 C31 F3 59.0(4) . . . . ? O1 S1 C31 F3 177.1(4) . . . . ? O6 S2 C32 F6 179.6(5) . . . . ? O4 S2 C32 F6 60.4(6) . . . . ? O5 S2 C32 F6 -59.2(6) . . . . ? O6 S2 C32 F4 59.2(6) . . . . ? O4 S2 C32 F4 -60.0(6) . . . . ? O5 S2 C32 F4 -179.7(5) . . . . ? O6 S2 C32 F5 -61.4(6) . . . . ? O4 S2 C32 F5 179.4(5) . . . . ? O5 S2 C32 F5 59.7(6) . . . . ? Cu2 N33 C34 C35 5E1(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 N18 H18 O4 0.911(19) 2.43(5) 2.972(6) 118(4) . # END of CIF data_cdr18-03 _database_code_depnum_ccdc_archive 'CCDC 844325' _audit_creation_date 2011-09-08T13:18:24-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C22 H16 Cu2 N10 O7, 5(H2 O)' _chemical_formula_sum 'C22 H26 Cu2 N10 O12' _chemical_formula_weight 749.61 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.2424(2) _cell_length_b 12.4631(4) _cell_length_c 15.7040(4) _cell_angle_alpha 82.150(2) _cell_angle_beta 85.467(2) _cell_angle_gamma 78.319(2) _cell_volume 1373.19(7) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 6093 _cell_measurement_theta_min 0.407 _cell_measurement_theta_max 28.283 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour blue _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn 1.813 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 764 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 1.633 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 2008)' _exptl_absorpt_correction_T_min 0.638 _exptl_absorpt_correction_T_max 0.746 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0476 _diffrn_reflns_av_unetI/netI 0.0524 _diffrn_reflns_number 17808 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.62 _diffrn_reflns_theta_max 25.49 _diffrn_reflns_theta_full 25.49 _diffrn_measured_fraction_theta_full 0.99 _diffrn_measured_fraction_theta_max 0.99 _reflns_number_total 5055 _reflns_number_gt 4137 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SIR92 (Giacovazzo et al, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^ > 2\s(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^)+(0.0000P)^2^+2.8602P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 5055 _refine_ls_number_parameters 460 _refine_ls_number_restraints 16 _refine_ls_R_factor_all 0.0514 _refine_ls_R_factor_gt 0.0378 _refine_ls_wR_factor_ref 0.0823 _refine_ls_wR_factor_gt 0.0772 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.399 _refine_diff_density_min -0.362 _refine_diff_density_rms 0.085 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' 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 0.87911(5) 0.30282(3) 0.18440(2) 0.01547(11) Uani 1 1 d . . . Cu2 Cu 0.98602(5) 0.22287(3) 0.35403(2) 0.01333(11) Uani 1 1 d . . . O1 O 1.0153(3) 0.16305(18) 0.24416(13) 0.0149(5) Uani 1 1 d D . . H1 H 1.134(3) 0.150(3) 0.225(2) 0.022 Uiso 1 1 d D . . O2 O 1.1568(3) 0.3841(2) 0.19505(14) 0.0240(5) Uani 1 1 d . . . O3 O 1.1616(3) 0.36231(18) 0.33448(14) 0.0189(5) Uani 1 1 d . . . O4 O 1.3454(3) 0.45957(19) 0.25687(15) 0.0236(5) Uani 1 1 d . . . O5 O 0.4870(3) 0.18728(19) 0.27391(14) 0.0240(5) Uani 1 1 d . . . O6 O 0.3889(3) 0.1251(2) 0.16696(16) 0.0279(6) Uani 1 1 d . . . O7 O 0.6162(3) 0.2161(2) 0.14517(15) 0.0310(6) Uani 1 1 d . . . O8 O 0.5815(4) 0.8575(2) 0.26356(19) 0.0357(7) Uani 1 1 d D . . H8B H 0.680(4) 0.889(3) 0.244(2) 0.036 Uiso 1 1 d D . . H8A H 0.632(6) 0.7866(19) 0.280(3) 0.054 Uiso 1 1 d D . . O9 O 0.8933(4) 0.9766(2) 0.2085(2) 0.0427(8) Uani 1 1 d D . . H9A H 1.014(3) 0.944(4) 0.205(3) 0.064 Uiso 1 1 d D . . H9B H 0.905(7) 1.046(2) 0.211(3) 0.064 Uiso 1 1 d D . . O10 O 1.4390(3) 0.3065(2) 0.45890(16) 0.0260(6) Uani 1 1 d D . . H10A H 1.349(4) 0.321(3) 0.421(2) 0.039 Uiso 1 1 d D . . H10B H 1.381(5) 0.334(3) 0.5050(18) 0.039 Uiso 1 1 d D . . O11 O 0.2679(5) 0.8755(3) 0.1619(3) 0.0587(10) Uani 1 1 d D . . H11A H 0.355(6) 0.889(5) 0.194(3) 0.088 Uiso 1 1 d D . . H11B H 0.298(9) 0.906(5) 0.110(2) 0.088 Uiso 1 1 d D . . O12A O 0.6383(19) 0.0750(9) -0.0042(5) 0.044(2) Uani 0.5 1 d PD . . O12B O 0.6554(18) 0.0413(8) 0.0294(7) 0.045(2) Uani 0.5 1 d PD . . H12A H 0.542(2) 0.060(2) 0.018(3) 0.068 Uiso 1 1 d D . . H12B H 0.686(5) 0.096(3) 0.037(2) 0.068 Uiso 1 1 d D . . N1 N 0.9509(4) 0.2858(2) 0.06184(16) 0.0171(6) Uani 1 1 d . . . N2 N 1.2231(4) 0.4028(2) 0.26154(16) 0.0156(6) Uani 1 1 d . . . N3 N 0.4977(4) 0.1763(2) 0.19614(18) 0.0197(6) Uani 1 1 d . . . N12 N 0.7618(4) 0.4553(2) 0.13404(16) 0.0161(6) Uani 1 1 d . . . N14 N 0.6792(4) 0.6113(2) 0.31622(17) 0.0178(6) Uani 1 1 d . . . N15 N 0.7164(4) 0.5674(2) 0.40053(16) 0.0168(6) Uani 1 1 d . . . N17 N 0.7423(3) 0.4308(2) 0.32319(16) 0.0130(5) Uani 1 1 d . . . N18 N 0.7707(4) 0.3235(2) 0.30025(16) 0.0133(5) Uani 1 1 d D . . H18 H 0.664(3) 0.297(3) 0.311(2) 0.02 Uiso 1 1 d D . . N24 N 0.9263(3) 0.2829(2) 0.46675(16) 0.0128(5) Uani 1 1 d . . . N30 N 1.1494(4) 0.1033(2) 0.42515(16) 0.0138(6) Uani 1 1 d . . . C2 C 1.0528(5) 0.1954(3) 0.0314(2) 0.0228(8) Uani 1 1 d . . . H2 H 1.1065 0.1343 0.0707 0.027 Uiso 1 1 calc R . . C3 C 1.0814(5) 0.1891(3) -0.0565(2) 0.0289(9) Uani 1 1 d . . . H3 H 1.1564 0.1252 -0.0773 0.035 Uiso 1 1 calc R . . C4 C 0.9992(5) 0.2770(3) -0.1129(2) 0.0272(8) Uani 1 1 d . . . H4 H 1.0158 0.2736 -0.1732 0.033 Uiso 1 1 calc R . . C5 C 0.8921(5) 0.3708(3) -0.0820(2) 0.0226(8) Uani 1 1 d . . . H5 H 0.8347 0.432 -0.1203 0.027 Uiso 1 1 calc R . . C6 C 0.8713(4) 0.3725(3) 0.0068(2) 0.0178(7) Uani 1 1 d . . . C7 C 0.7644(4) 0.4690(3) 0.0470(2) 0.0175(7) Uani 1 1 d . . . C8 C 0.6756(5) 0.5666(3) 0.0013(2) 0.0212(8) Uani 1 1 d . . . H8 H 0.6794 0.5755 -0.0598 0.025 Uiso 1 1 calc R . . C9 C 0.5812(5) 0.6507(3) 0.0469(2) 0.0225(8) Uani 1 1 d . . . H9 H 0.5158 0.7173 0.0171 0.027 Uiso 1 1 calc R . . C10 C 0.5819(5) 0.6379(3) 0.1358(2) 0.0201(7) Uani 1 1 d . . . H10 H 0.5187 0.6956 0.1675 0.024 Uiso 1 1 calc R . . C11 C 0.6764(4) 0.5396(3) 0.1777(2) 0.0163(7) Uani 1 1 d . . . C13 C 0.6961(4) 0.5273(3) 0.2712(2) 0.0147(7) Uani 1 1 d . . . C16 C 0.7555(4) 0.4584(3) 0.4032(2) 0.0148(7) Uani 1 1 d . . . C19 C 0.8171(4) 0.3812(2) 0.4799(2) 0.0137(7) Uani 1 1 d . . . C20 C 0.7709(5) 0.4104(3) 0.5621(2) 0.0171(7) Uani 1 1 d . . . H20 H 0.694 0.4799 0.5707 0.021 Uiso 1 1 calc R . . C21 C 0.8395(5) 0.3361(3) 0.6312(2) 0.0202(7) Uani 1 1 d . . . H21 H 0.8066 0.3535 0.6882 0.024 Uiso 1 1 calc R . . C22 C 0.9557(5) 0.2365(3) 0.6180(2) 0.0174(7) Uani 1 1 d . . . H22 H 1.0049 0.1857 0.6654 0.021 Uiso 1 1 calc R . . C23 C 0.9987(4) 0.2123(2) 0.53463(19) 0.0129(6) Uani 1 1 d . . . C25 C 1.1231(4) 0.1100(3) 0.5108(2) 0.0144(7) Uani 1 1 d . . . C26 C 1.2097(4) 0.0249(3) 0.5702(2) 0.0156(7) Uani 1 1 d . . . H26 H 1.1923 0.0307 0.6301 0.019 Uiso 1 1 calc R . . C27 C 1.3216(4) -0.0682(3) 0.5409(2) 0.0169(7) Uani 1 1 d . . . H27 H 1.3795 -0.1276 0.5806 0.02 Uiso 1 1 calc R . . C28 C 1.3481(4) -0.0737(3) 0.4530(2) 0.0174(7) Uani 1 1 d . . . H28 H 1.4253 -0.1364 0.4315 0.021 Uiso 1 1 calc R . . C29 C 1.2603(4) 0.0138(3) 0.3973(2) 0.0169(7) Uani 1 1 d . . . H29 H 1.279 0.0104 0.3371 0.02 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 0.0188(2) 0.0174(2) 0.0099(2) -0.00086(16) -0.00122(16) -0.00302(17) Cu2 0.0159(2) 0.0139(2) 0.0102(2) -0.00182(15) -0.00156(15) -0.00233(16) O1 0.0160(11) 0.0183(12) 0.0111(11) -0.0046(9) -0.0008(9) -0.0032(10) O2 0.0297(13) 0.0313(14) 0.0143(12) 0.0025(10) -0.0066(11) -0.0150(11) O3 0.0200(12) 0.0233(12) 0.0147(12) 0.0003(10) -0.0004(10) -0.0088(10) O4 0.0215(12) 0.0259(13) 0.0287(14) -0.0041(11) 0.0007(10) -0.0171(11) O5 0.0322(14) 0.0287(13) 0.0135(12) -0.0018(10) -0.0014(10) -0.0119(11) O6 0.0222(13) 0.0355(15) 0.0323(14) -0.0178(12) -0.0023(11) -0.0108(11) O7 0.0268(13) 0.0541(17) 0.0165(13) -0.0013(12) 0.0028(11) -0.0214(13) O8 0.0391(16) 0.0276(15) 0.0422(17) -0.0091(13) -0.0001(14) -0.0080(13) O9 0.0335(15) 0.0405(17) 0.063(2) -0.0330(16) 0.0073(15) -0.0135(14) O10 0.0271(14) 0.0279(14) 0.0215(14) -0.0087(11) -0.0067(11) 0.0044(11) O11 0.0341(17) 0.044(2) 0.104(3) -0.038(2) -0.017(2) 0.0009(15) O12A 0.049(5) 0.044(6) 0.033(6) -0.005(4) 0.001(5) 0.000(4) O12B 0.046(5) 0.043(6) 0.043(6) -0.015(4) 0.004(5) 0.006(4) N1 0.0167(14) 0.0255(15) 0.0096(13) -0.0018(11) -0.0021(11) -0.0050(12) N2 0.0151(13) 0.0167(14) 0.0141(14) -0.0019(11) 0.0007(12) -0.0013(12) N3 0.0176(14) 0.0229(15) 0.0187(15) -0.0036(12) -0.0023(12) -0.0030(12) N12 0.0172(14) 0.0194(14) 0.0124(14) 0.0005(11) -0.0028(11) -0.0063(12) N14 0.0212(14) 0.0165(14) 0.0153(14) 0.0019(11) -0.0041(12) -0.0044(12) N15 0.0210(14) 0.0149(14) 0.0138(14) -0.0003(11) -0.0039(12) -0.0017(12) N17 0.0131(13) 0.0130(13) 0.0132(13) -0.0012(11) -0.0004(11) -0.0032(11) N18 0.0164(14) 0.0123(13) 0.0123(13) -0.0030(11) -0.0002(11) -0.0041(11) N24 0.0137(13) 0.0139(13) 0.0112(13) -0.0005(11) -0.0008(11) -0.0044(11) N30 0.0133(13) 0.0172(14) 0.0110(13) -0.0010(11) 0.0008(11) -0.0041(11) C2 0.0194(17) 0.031(2) 0.0187(18) -0.0038(15) -0.0034(15) -0.0045(15) C3 0.0227(18) 0.046(2) 0.0207(19) -0.0134(17) -0.0017(16) -0.0061(17) C4 0.0271(19) 0.043(2) 0.0143(17) -0.0072(16) 0.0025(15) -0.0135(18) C5 0.0254(18) 0.0280(19) 0.0160(17) -0.0004(15) -0.0025(15) -0.0102(16) C6 0.0179(16) 0.0262(18) 0.0126(16) -0.0015(14) -0.0022(14) -0.0123(15) C7 0.0149(16) 0.0239(18) 0.0156(17) 0.0005(14) -0.0023(13) -0.0094(14) C8 0.0219(18) 0.0273(19) 0.0160(17) 0.0033(15) -0.0082(14) -0.0096(15) C9 0.0212(18) 0.0229(18) 0.0231(19) 0.0070(15) -0.0102(15) -0.0072(15) C10 0.0210(17) 0.0194(17) 0.0196(18) 0.0014(14) -0.0032(14) -0.0049(14) C11 0.0147(15) 0.0190(17) 0.0155(16) 0.0019(13) -0.0012(13) -0.0069(14) C13 0.0136(15) 0.0153(16) 0.0145(16) 0.0014(13) -0.0004(13) -0.0029(13) C16 0.0127(15) 0.0179(17) 0.0133(16) -0.0031(13) 0.0007(13) -0.0017(13) C19 0.0145(15) 0.0116(15) 0.0158(16) -0.0013(13) -0.0028(13) -0.0038(13) C20 0.0206(17) 0.0135(16) 0.0174(17) -0.0043(13) 0.0006(14) -0.0025(14) C21 0.0264(18) 0.0230(18) 0.0131(16) -0.0067(14) -0.0001(14) -0.0065(15) C22 0.0209(17) 0.0181(17) 0.0130(16) 0.0008(13) -0.0040(14) -0.0042(14) C23 0.0133(15) 0.0147(16) 0.0124(16) 0.0000(13) -0.0004(13) -0.0074(13) C25 0.0135(15) 0.0157(16) 0.0151(16) -0.0001(13) -0.0010(13) -0.0065(13) C26 0.0149(16) 0.0182(17) 0.0145(16) -0.0005(13) 0.0006(13) -0.0069(14) C27 0.0151(16) 0.0144(16) 0.0207(18) 0.0023(13) -0.0025(14) -0.0042(13) C28 0.0124(15) 0.0155(16) 0.0237(18) -0.0029(14) -0.0003(14) -0.0015(13) C29 0.0148(16) 0.0205(17) 0.0157(17) -0.0041(14) 0.0013(14) -0.0040(14) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 N18 1.953(3) . ? Cu1 O1 1.973(2) . ? Cu1 N1 1.982(3) . ? Cu1 N12 2.000(3) . ? Cu1 Cu2 2.8244(5) . ? Cu2 O1 1.951(2) . ? Cu2 N18 1.961(3) . ? Cu2 N30 1.977(3) . ? Cu2 N24 1.997(2) . ? Cu2 O3 2.328(2) . ? O1 H1 0.879(18) . ? O2 N2 1.252(3) . ? O3 N2 1.272(3) . ? O4 N2 1.233(3) . ? O5 N3 1.242(3) . ? O6 N3 1.257(3) . ? O7 N3 1.256(4) . ? O8 H8B 0.895(19) . ? O8 H8A 0.896(19) . ? O9 H9A 0.89(2) . ? O9 H9B 0.896(19) . ? O10 H10A 0.887(19) . ? O10 H10B 0.885(19) . ? O11 H11A 0.89(2) . ? O11 H11B 0.88(2) . ? O12A O12B 0.631(9) . ? O12A H12A 0.800(19) . ? O12A H12B 0.848(19) . ? O12B H12A 0.829(19) . ? O12B H12B 0.786(19) . ? N1 C2 1.341(4) . ? N1 C6 1.349(4) . ? N12 C11 1.350(4) . ? N12 C7 1.354(4) . ? N14 C13 1.322(4) . ? N14 N15 1.387(4) . ? N15 C16 1.326(4) . ? N17 C13 1.356(4) . ? N17 C16 1.364(4) . ? N17 N18 1.403(3) . ? N18 H18 0.893(18) . ? N24 C19 1.349(4) . ? N24 C23 1.353(4) . ? N30 C29 1.340(4) . ? N30 C25 1.356(4) . ? C2 C3 1.390(5) . ? C2 H2 0.95 . ? C3 C4 1.376(5) . ? C3 H3 0.95 . ? C4 C5 1.390(5) . ? C4 H4 0.95 . ? C5 C6 1.393(4) . ? C5 H5 0.95 . ? C6 C7 1.482(5) . ? C7 C8 1.388(5) . ? C8 C9 1.384(5) . ? C8 H8 0.95 . ? C9 C10 1.384(5) . ? C9 H9 0.95 . ? C10 C11 1.383(4) . ? C10 H10 0.95 . ? C11 C13 1.471(4) . ? C16 C19 1.472(4) . ? C19 C20 1.387(4) . ? C20 C21 1.381(5) . ? C20 H20 0.95 . ? C21 C22 1.382(5) . ? C21 H21 0.95 . ? C22 C23 1.382(4) . ? C22 H22 0.95 . ? C23 C25 1.479(4) . ? C25 C26 1.392(4) . ? C26 C27 1.386(4) . ? C26 H26 0.95 . ? C27 C28 1.388(4) . ? C27 H27 0.95 . ? C28 C29 1.380(4) . ? C28 H28 0.95 . ? C29 H29 0.95 . ? 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 N18 Cu1 O1 82.60(10) . . ? N18 Cu1 N1 171.72(11) . . ? O1 Cu1 N1 102.25(10) . . ? N18 Cu1 N12 93.78(11) . . ? O1 Cu1 N12 171.68(10) . . ? N1 Cu1 N12 82.27(11) . . ? N18 Cu1 Cu2 43.91(7) . . ? O1 Cu1 Cu2 43.66(6) . . ? N1 Cu1 Cu2 143.07(8) . . ? N12 Cu1 Cu2 129.82(7) . . ? O1 Cu2 N18 82.96(10) . . ? O1 Cu2 N30 100.65(10) . . ? N18 Cu2 N30 164.75(11) . . ? O1 Cu2 N24 173.74(10) . . ? N18 Cu2 N24 92.94(10) . . ? N30 Cu2 N24 82.12(10) . . ? O1 Cu2 O3 104.93(9) . . ? N18 Cu2 O3 90.88(9) . . ? N30 Cu2 O3 102.34(9) . . ? N24 Cu2 O3 79.79(9) . . ? O1 Cu2 Cu1 44.28(6) . . ? N18 Cu2 Cu1 43.69(7) . . ? N30 Cu2 Cu1 144.18(7) . . ? N24 Cu2 Cu1 133.57(7) . . ? O3 Cu2 Cu1 84.54(5) . . ? Cu2 O1 Cu1 92.07(9) . . ? Cu2 O1 H1 112(2) . . ? Cu1 O1 H1 110(2) . . ? N2 O3 Cu2 124.16(18) . . ? H8B O8 H8A 105(4) . . ? H9A O9 H9B 100(4) . . ? H10A O10 H10B 104(4) . . ? H11A O11 H11B 103(6) . . ? O12B O12A H12A 70(2) . . ? O12B O12A H12B 62(2) . . ? H12A O12A H12B 102(3) . . ? O12A O12B H12A 65(2) . . ? O12A O12B H12B 73(2) . . ? H12A O12B H12B 105(3) . . ? C2 N1 C6 119.9(3) . . ? C2 N1 Cu1 126.2(2) . . ? C6 N1 Cu1 113.5(2) . . ? O4 N2 O2 120.9(3) . . ? O4 N2 O3 120.3(2) . . ? O2 N2 O3 118.8(3) . . ? O5 N3 O7 121.1(3) . . ? O5 N3 O6 120.2(3) . . ? O7 N3 O6 118.7(3) . . ? C11 N12 C7 119.5(3) . . ? C11 N12 Cu1 126.8(2) . . ? C7 N12 Cu1 113.6(2) . . ? C13 N14 N15 107.1(2) . . ? C16 N15 N14 107.5(2) . . ? C13 N17 C16 106.2(2) . . ? C13 N17 N18 127.5(2) . . ? C16 N17 N18 126.3(3) . . ? N17 N18 Cu1 116.71(19) . . ? N17 N18 Cu2 113.50(18) . . ? Cu1 N18 Cu2 92.40(11) . . ? N17 N18 H18 110(2) . . ? Cu1 N18 H18 111(2) . . ? Cu2 N18 H18 112(2) . . ? C19 N24 C23 119.8(3) . . ? C19 N24 Cu2 126.3(2) . . ? C23 N24 Cu2 113.8(2) . . ? C29 N30 C25 119.6(3) . . ? C29 N30 Cu2 126.2(2) . . ? C25 N30 Cu2 113.7(2) . . ? N1 C2 C3 121.4(3) . . ? N1 C2 H2 119.3 . . ? C3 C2 H2 119.3 . . ? C4 C3 C2 118.9(3) . . ? C4 C3 H3 120.6 . . ? C2 C3 H3 120.6 . . ? C3 C4 C5 120.2(3) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C4 C5 C6 118.1(3) . . ? C4 C5 H5 120.9 . . ? C6 C5 H5 120.9 . . ? N1 C6 C5 121.5(3) . . ? N1 C6 C7 115.6(3) . . ? C5 C6 C7 122.9(3) . . ? N12 C7 C8 121.5(3) . . ? N12 C7 C6 114.1(3) . . ? C8 C7 C6 124.3(3) . . ? C9 C8 C7 118.4(3) . . ? C9 C8 H8 120.8 . . ? C7 C8 H8 120.8 . . ? C10 C9 C8 120.2(3) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C11 C10 C9 118.8(3) . . ? C11 C10 H10 120.6 . . ? C9 C10 H10 120.6 . . ? N12 C11 C10 121.5(3) . . ? N12 C11 C13 118.2(3) . . ? C10 C11 C13 120.1(3) . . ? N14 C13 N17 110.0(3) . . ? N14 C13 C11 123.9(3) . . ? N17 C13 C11 126.1(3) . . ? N15 C16 N17 109.2(3) . . ? N15 C16 C19 124.6(3) . . ? N17 C16 C19 126.1(3) . . ? N24 C19 C20 121.5(3) . . ? N24 C19 C16 117.4(3) . . ? C20 C19 C16 121.1(3) . . ? C21 C20 C19 118.3(3) . . ? C21 C20 H20 120.8 . . ? C19 C20 H20 120.8 . . ? C20 C21 C22 120.5(3) . . ? C20 C21 H21 119.8 . . ? C22 C21 H21 119.8 . . ? C23 C22 C21 118.6(3) . . ? C23 C22 H22 120.7 . . ? C21 C22 H22 120.7 . . ? N24 C23 C22 121.2(3) . . ? N24 C23 C25 114.2(3) . . ? C22 C23 C25 124.6(3) . . ? N30 C25 C26 120.8(3) . . ? N30 C25 C23 115.2(3) . . ? C26 C25 C23 124.0(3) . . ? C27 C26 C25 119.3(3) . . ? C27 C26 H26 120.3 . . ? C25 C26 H26 120.3 . . ? C26 C27 C28 119.3(3) . . ? C26 C27 H27 120.4 . . ? C28 C27 H27 120.4 . . ? C29 C28 C27 118.7(3) . . ? C29 C28 H28 120.6 . . ? C27 C28 H28 120.6 . . ? N30 C29 C28 122.3(3) . . ? N30 C29 H29 118.8 . . ? C28 C29 H29 118.8 . . ? 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 N18 Cu1 Cu2 O1 145.03(14) . . . . ? N1 Cu1 Cu2 O1 -28.07(16) . . . . ? N12 Cu1 Cu2 O1 -172.90(14) . . . . ? O1 Cu1 Cu2 N18 -145.03(14) . . . . ? N1 Cu1 Cu2 N18 -173.10(17) . . . . ? N12 Cu1 Cu2 N18 42.07(15) . . . . ? N18 Cu1 Cu2 N30 159.41(17) . . . . ? O1 Cu1 Cu2 N30 14.39(16) . . . . ? N1 Cu1 Cu2 N30 -13.69(19) . . . . ? N12 Cu1 Cu2 N30 -158.51(16) . . . . ? N18 Cu1 Cu2 N24 -26.70(15) . . . . ? O1 Cu1 Cu2 N24 -171.73(14) . . . . ? N1 Cu1 Cu2 N24 160.20(16) . . . . ? N12 Cu1 Cu2 N24 15.37(14) . . . . ? N18 Cu1 Cu2 O3 -97.03(12) . . . . ? O1 Cu1 Cu2 O3 117.95(11) . . . . ? N1 Cu1 Cu2 O3 89.87(14) . . . . ? N12 Cu1 Cu2 O3 -54.95(11) . . . . ? N18 Cu2 O1 Cu1 23.51(10) . . . . ? N30 Cu2 O1 Cu1 -171.49(9) . . . . ? N24 Cu2 O1 Cu1 72.8(9) . . . . ? O3 Cu2 O1 Cu1 -65.51(9) . . . . ? N18 Cu1 O1 Cu2 -23.63(10) . . . . ? N1 Cu1 O1 Cu2 163.18(9) . . . . ? N12 Cu1 O1 Cu2 41.0(7) . . . . ? O1 Cu2 O3 N2 13.9(2) . . . . ? N18 Cu2 O3 N2 -69.0(2) . . . . ? N30 Cu2 O3 N2 118.6(2) . . . . ? N24 Cu2 O3 N2 -161.9(2) . . . . ? Cu1 Cu2 O3 N2 -25.7(2) . . . . ? N18 Cu1 N1 C2 -119.8(7) . . . . ? O1 Cu1 N1 C2 5.4(3) . . . . ? N12 Cu1 N1 C2 178.3(3) . . . . ? Cu2 Cu1 N1 C2 24.8(3) . . . . ? N18 Cu1 N1 C6 53.9(9) . . . . ? O1 Cu1 N1 C6 179.2(2) . . . . ? N12 Cu1 N1 C6 -7.9(2) . . . . ? Cu2 Cu1 N1 C6 -161.40(16) . . . . ? Cu2 O3 N2 O4 -165.3(2) . . . . ? Cu2 O3 N2 O2 14.9(4) . . . . ? N18 Cu1 N12 C11 11.8(3) . . . . ? O1 Cu1 N12 C11 -52.1(8) . . . . ? N1 Cu1 N12 C11 -175.6(3) . . . . ? Cu2 Cu1 N12 C11 -16.0(3) . . . . ? N18 Cu1 N12 C7 -164.9(2) . . . . ? O1 Cu1 N12 C7 131.2(6) . . . . ? N1 Cu1 N12 C7 7.8(2) . . . . ? Cu2 Cu1 N12 C7 167.33(17) . . . . ? C13 N14 N15 C16 0.4(3) . . . . ? C13 N17 N18 Cu1 33.1(4) . . . . ? C16 N17 N18 Cu1 -147.0(2) . . . . ? C13 N17 N18 Cu2 138.8(3) . . . . ? C16 N17 N18 Cu2 -41.4(3) . . . . ? O1 Cu1 N18 N17 141.4(2) . . . . ? N1 Cu1 N18 N17 -92.2(8) . . . . ? N12 Cu1 N18 N17 -31.0(2) . . . . ? Cu2 Cu1 N18 N17 117.9(2) . . . . ? O1 Cu1 N18 Cu2 23.52(9) . . . . ? N1 Cu1 N18 Cu2 149.9(7) . . . . ? N12 Cu1 N18 Cu2 -148.95(11) . . . . ? O1 Cu2 N18 N17 -144.4(2) . . . . ? N30 Cu2 N18 N17 110.9(4) . . . . ? N24 Cu2 N18 N17 40.4(2) . . . . ? O3 Cu2 N18 N17 -39.4(2) . . . . ? Cu1 Cu2 N18 N17 -120.6(2) . . . . ? O1 Cu2 N18 Cu1 -23.78(10) . . . . ? N30 Cu2 N18 Cu1 -128.5(4) . . . . ? N24 Cu2 N18 Cu1 160.97(10) . . . . ? O3 Cu2 N18 Cu1 81.15(10) . . . . ? O1 Cu2 N24 C19 -68.1(10) . . . . ? N18 Cu2 N24 C19 -19.2(3) . . . . ? N30 Cu2 N24 C19 175.3(3) . . . . ? O3 Cu2 N24 C19 71.1(2) . . . . ? Cu1 Cu2 N24 C19 -1.1(3) . . . . ? O1 Cu2 N24 C23 108.5(9) . . . . ? N18 Cu2 N24 C23 157.4(2) . . . . ? N30 Cu2 N24 C23 -8.1(2) . . . . ? O3 Cu2 N24 C23 -112.2(2) . . . . ? Cu1 Cu2 N24 C23 175.50(16) . . . . ? O1 Cu2 N30 C29 5.9(3) . . . . ? N18 Cu2 N30 C29 108.4(4) . . . . ? N24 Cu2 N30 C29 -179.8(3) . . . . ? O3 Cu2 N30 C29 -102.1(3) . . . . ? Cu1 Cu2 N30 C29 -4.2(3) . . . . ? O1 Cu2 N30 C25 -165.5(2) . . . . ? N18 Cu2 N30 C25 -63.0(5) . . . . ? N24 Cu2 N30 C25 8.8(2) . . . . ? O3 Cu2 N30 C25 86.5(2) . . . . ? Cu1 Cu2 N30 C25 -175.64(15) . . . . ? C6 N1 C2 C3 1.0(5) . . . . ? Cu1 N1 C2 C3 174.4(3) . . . . ? N1 C2 C3 C4 -1.5(5) . . . . ? C2 C3 C4 C5 1.0(5) . . . . ? C3 C4 C5 C6 0.0(5) . . . . ? C2 N1 C6 C5 0.0(5) . . . . ? Cu1 N1 C6 C5 -174.2(2) . . . . ? C2 N1 C6 C7 -179.0(3) . . . . ? Cu1 N1 C6 C7 6.8(3) . . . . ? C4 C5 C6 N1 -0.5(5) . . . . ? C4 C5 C6 C7 178.4(3) . . . . ? C11 N12 C7 C8 -2.3(4) . . . . ? Cu1 N12 C7 C8 174.6(2) . . . . ? C11 N12 C7 C6 176.8(3) . . . . ? Cu1 N12 C7 C6 -6.2(3) . . . . ? N1 C6 C7 N12 -0.3(4) . . . . ? C5 C6 C7 N12 -179.4(3) . . . . ? N1 C6 C7 C8 178.8(3) . . . . ? C5 C6 C7 C8 -0.3(5) . . . . ? N12 C7 C8 C9 -0.6(5) . . . . ? C6 C7 C8 C9 -179.6(3) . . . . ? C7 C8 C9 C10 2.1(5) . . . . ? C8 C9 C10 C11 -0.7(5) . . . . ? C7 N12 C11 C10 3.7(5) . . . . ? Cu1 N12 C11 C10 -172.7(2) . . . . ? C7 N12 C11 C13 -172.5(3) . . . . ? Cu1 N12 C11 C13 11.0(4) . . . . ? C9 C10 C11 N12 -2.2(5) . . . . ? C9 C10 C11 C13 173.9(3) . . . . ? N15 N14 C13 N17 0.1(3) . . . . ? N15 N14 C13 C11 -177.0(3) . . . . ? C16 N17 C13 N14 -0.6(3) . . . . ? N18 N17 C13 N14 179.3(3) . . . . ? C16 N17 C13 C11 176.4(3) . . . . ? N18 N17 C13 C11 -3.7(5) . . . . ? N12 C11 C13 N14 155.8(3) . . . . ? C10 C11 C13 N14 -20.5(5) . . . . ? N12 C11 C13 N17 -20.8(5) . . . . ? C10 C11 C13 N17 162.9(3) . . . . ? N14 N15 C16 N17 -0.8(3) . . . . ? N14 N15 C16 C19 175.1(3) . . . . ? C13 N17 C16 N15 0.9(3) . . . . ? N18 N17 C16 N15 -179.0(3) . . . . ? C13 N17 C16 C19 -174.9(3) . . . . ? N18 N17 C16 C19 5.2(5) . . . . ? C23 N24 C19 C20 -2.4(4) . . . . ? Cu2 N24 C19 C20 174.0(2) . . . . ? C23 N24 C19 C16 175.0(3) . . . . ? Cu2 N24 C19 C16 -8.6(4) . . . . ? N15 C16 C19 N24 -152.0(3) . . . . ? N17 C16 C19 N24 23.2(5) . . . . ? N15 C16 C19 C20 25.4(5) . . . . ? N17 C16 C19 C20 -159.4(3) . . . . ? N24 C19 C20 C21 0.0(5) . . . . ? C16 C19 C20 C21 -177.4(3) . . . . ? C19 C20 C21 C22 1.8(5) . . . . ? C20 C21 C22 C23 -1.1(5) . . . . ? C19 N24 C23 C22 3.1(4) . . . . ? Cu2 N24 C23 C22 -173.7(2) . . . . ? C19 N24 C23 C25 -177.2(3) . . . . ? Cu2 N24 C23 C25 6.0(3) . . . . ? C21 C22 C23 N24 -1.4(5) . . . . ? C21 C22 C23 C25 179.0(3) . . . . ? C29 N30 C25 C26 -0.1(4) . . . . ? Cu2 N30 C25 C26 171.9(2) . . . . ? C29 N30 C25 C23 179.9(3) . . . . ? Cu2 N30 C25 C23 -8.1(3) . . . . ? N24 C23 C25 N30 1.4(4) . . . . ? C22 C23 C25 N30 -179.0(3) . . . . ? N24 C23 C25 C26 -178.6(3) . . . . ? C22 C23 C25 C26 1.0(5) . . . . ? N30 C25 C26 C27 -1.0(4) . . . . ? C23 C25 C26 C27 179.0(3) . . . . ? C25 C26 C27 C28 1.3(5) . . . . ? C26 C27 C28 C29 -0.6(5) . . . . ? C25 N30 C29 C28 0.8(5) . . . . ? Cu2 N30 C29 C28 -170.1(2) . . . . ? C27 C28 C29 N30 -0.5(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 O1 H1 O6 0.879(18) 1.977(19) 2.852(3) 173(3) 1_655 O8 H8B O9 0.895(19) 2.07(2) 2.958(4) 173(4) . O8 H8A N14 0.896(19) 2.14(2) 3.019(4) 165(4) . O9 H9A O11 0.89(2) 1.97(2) 2.835(4) 163(5) 1_655 O9 H9B O1 0.896(19) 1.94(3) 2.785(3) 156(5) 1_565 O10 H10A O3 0.887(19) 1.95(2) 2.832(3) 175(4) . O10 H10B N15 0.885(19) 2.04(2) 2.907(4) 165(4) 2_766 O11 H11A O8 0.89(2) 1.98(3) 2.834(4) 159(5) . O11 H11B O12A 0.88(2) 1.68(3) 2.541(9) 163(6) 2_665 O12B H12B O7 0.786(19) 2.38(3) 2.980(12) 135(4) . O12A H12A O12B 0.800(19) 2.313(19) 2.885(9) 129(3) 2_655 O12A H12A O12A 0.800(19) 2.37(2) 2.99(3) 135(2) 2_655 N18 H18 O5 0.893(18) 2.21(2) 3.002(3) 147(3) . # END of CIF