# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 #TrackingRef 'CCDC 747625.cif' #============================================================================== # Person making the deposition # _publ_contact_author 'Myunghyun Paik Suh' _publ_contact_author_email mpsuh@snu.ac.kr _publ_contact_author_address ; Department of Chemistry, Seoul National University, Sillim-dong, Kwanak-gu, Seoul 151-747, Republic of Korea ; _publ_contact_author_fax '(+82) 2-886-8516' _publ_contact_author_phone '(+82) 2-880-7760' _publ_contact_author_name 'Myunghyun Paik Suh' loop_ _publ_author_name 'Hye Jeong Park' 'Myunghyun Paik Suh' #============================================================================== data_1 _database_code_depnum_ccdc_archive 'CCDC 747625' #TrackingRef 'CCDC 747625.cif' #============================================================================== _audit_creation_date 2011-12-10T20:59:32-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C42 H68 Cu2 N10 O12' _chemical_formula_sum 'C42 H68 Cu2 N10 O12' _chemical_formula_weight 1032.14 #----------------------------------------------------------------------------# # 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 7.8814(4) _cell_length_b 16.4329(13) _cell_length_c 18.0521(13) _cell_angle_alpha 90 _cell_angle_beta 90.406(4) _cell_angle_gamma 90 _cell_volume 2337.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.466 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.981 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_av_R_equivalents 0.0575 _diffrn_reflns_av_unetI/netI 0.0767 _diffrn_reflns_number 8869 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 27.5 _diffrn_reflns_theta_full 27.5 _diffrn_measured_fraction_theta_full 0.968 _diffrn_measured_fraction_theta_max 0.968 _reflns_number_total 5210 _reflns_number_gt 3456 _reflns_threshold_expression >2sigma(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, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # 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^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1243P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 5210 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1067 _refine_ls_R_factor_gt 0.0639 _refine_ls_wR_factor_ref 0.2061 _refine_ls_wR_factor_gt 0.1664 _refine_ls_goodness_of_fit_ref 1.06 _refine_ls_restrained_S_all 1.06 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0.001 _refine_diff_density_max 0.573 _refine_diff_density_min -1.24 _refine_diff_density_rms 0.217 #----------------------------------------------------------------------------# # 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 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' 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' O O 0.0106 0.006 '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 0.20487(5) 0.23417(3) 0.26332(2) 0.0356(2) Uani 1 1 d . . . N1 N 0.2003(4) 0.0826(2) 0.14011(17) 0.0402(8) Uani 1 1 d . . . N2 N 0.1451(4) 0.1155(2) 0.27153(17) 0.0346(7) Uani 1 1 d . . . H2 H 0.2413 0.0891 0.2861 0.042 Uiso 1 1 calc R . . N3 N 0.0817(4) 0.2459(2) 0.36006(19) 0.0370(8) Uani 1 1 d . . . H3 H -0.026 0.2619 0.3488 0.044 Uiso 1 1 calc R . . N4 N 0.2431(4) 0.3542(2) 0.25113(18) 0.0390(8) Uani 1 1 d . . . H4 H 0.1434 0.3749 0.2337 0.047 Uiso 1 1 calc R . . N5 N 0.3098(4) 0.2222(2) 0.16213(17) 0.0378(8) Uani 1 1 d . . . H5 H 0.4177 0.2038 0.1691 0.045 Uiso 1 1 calc R . . C1 C 0.5769(5) 0.0540(3) 0.0474(2) 0.0455(10) Uani 1 1 d . . . H1 H 0.6308 0.0906 0.079 0.055 Uiso 1 1 calc R . . C2 C 0.3541(5) -0.0383(3) 0.0218(2) 0.0451(10) Uani 1 1 d . . . H2A H 0.2553 -0.0648 0.0359 0.054 Uiso 1 1 calc R . . C3 C 0.4303(5) 0.0163(2) 0.0699(2) 0.0393(9) Uani 1 1 d . . . C4 C 0.3547(5) 0.0327(3) 0.1452(2) 0.0433(10) Uani 1 1 d . . . H4A H 0.3277 -0.0187 0.1688 0.052 Uiso 1 1 calc R . . H4B H 0.4379 0.0604 0.176 0.052 Uiso 1 1 calc R . . C5 C 0.0864(4) 0.0757(3) 0.2012(2) 0.0416(10) Uani 1 1 d . . . H5A H 0.0671 0.0184 0.211 0.05 Uiso 1 1 calc R . . H5B H -0.0216 0.0995 0.1868 0.05 Uiso 1 1 calc R . . C6 C 0.0214(5) 0.1052(3) 0.3314(2) 0.0420(10) Uani 1 1 d . . . H6A H 0.0234 0.0496 0.3494 0.05 Uiso 1 1 calc R . . H6B H -0.0921 0.1171 0.3134 0.05 Uiso 1 1 calc R . . C7 C 0.0691(5) 0.1631(3) 0.3931(2) 0.0416(10) Uani 1 1 d . . . H7A H -0.0166 0.1623 0.4314 0.05 Uiso 1 1 calc R . . H7B H 0.1769 0.1474 0.4151 0.05 Uiso 1 1 calc R . . C8 C 0.1509(5) 0.3066(3) 0.4128(2) 0.0466(10) Uani 1 1 d . . . H8A H 0.2646 0.2906 0.4278 0.056 Uiso 1 1 calc R . . H8B H 0.0809 0.3079 0.4568 0.056 Uiso 1 1 calc R . . C9 C 0.1563(6) 0.3906(3) 0.3785(3) 0.0561(12) Uani 1 1 d . . . H9A H 0.1803 0.4298 0.4173 0.067 Uiso 1 1 calc R . . H9B H 0.0447 0.403 0.3585 0.067 Uiso 1 1 calc R . . C10 C 0.2857(5) 0.4019(3) 0.3173(3) 0.0498(11) Uani 1 1 d . . . H10A H 0.2914 0.4591 0.3042 0.06 Uiso 1 1 calc R . . H10B H 0.3967 0.3856 0.3355 0.06 Uiso 1 1 calc R . . C11 C 0.3681(5) 0.3650(3) 0.1905(2) 0.0488(11) Uani 1 1 d . . . H11A H 0.4821 0.3545 0.2088 0.059 Uiso 1 1 calc R . . H11B H 0.3636 0.4203 0.1718 0.059 Uiso 1 1 calc R . . C12 C 0.3218(5) 0.3049(3) 0.1292(2) 0.0473(11) Uani 1 1 d . . . H12A H 0.2141 0.3199 0.1068 0.057 Uiso 1 1 calc R . . H12B H 0.408 0.3056 0.0911 0.057 Uiso 1 1 calc R . . C13 C 0.2226(5) 0.1637(3) 0.1111(2) 0.0439(10) Uani 1 1 d . . . H13A H 0.1119 0.1855 0.0983 0.053 Uiso 1 1 calc R . . H13B H 0.2874 0.1601 0.0657 0.053 Uiso 1 1 calc R . . C14 C 0.5151(5) 0.1475(3) 0.3671(2) 0.0416(10) Uani 1 1 d . . . C15 C 0.8775(5) 0.1565(3) 0.6507(2) 0.0417(10) Uani 1 1 d . . . C16 C 0.6076(4) 0.1511(3) 0.4411(2) 0.0384(9) Uani 1 1 d . . . C17 C 0.6518(5) 0.0795(3) 0.4769(2) 0.0497(11) Uani 1 1 d . . . H17 H 0.6238 0.0298 0.4554 0.06 Uiso 1 1 calc R . . C18 C 0.7371(5) 0.0812(3) 0.5443(2) 0.0493(11) Uani 1 1 d . . . H18 H 0.7633 0.0326 0.5683 0.059 Uiso 1 1 calc R . . C19 C 0.7835(4) 0.1543(3) 0.5761(2) 0.0370(9) Uani 1 1 d . . . C20 C 0.7405(5) 0.2261(2) 0.5406(2) 0.0364(9) Uani 1 1 d . . . H20 H 0.7702 0.2757 0.5618 0.044 Uiso 1 1 calc R . . C21 C 0.6529(5) 0.2246(2) 0.4734(2) 0.0381(9) Uani 1 1 d . . . H21 H 0.6245 0.2732 0.45 0.046 Uiso 1 1 calc R . . O1 O 0.4825(4) 0.2146(2) 0.33469(16) 0.0519(8) Uani 1 1 d . . . O2 O 0.4734(5) 0.0795(2) 0.3427(2) 0.0758(12) Uani 1 1 d . . . O3 O 0.9065(4) 0.2240(2) 0.67972(17) 0.0525(8) Uani 1 1 d . . . O4 O 0.9257(5) 0.0918(2) 0.6768(2) 0.0883(14) Uani 1 1 d . . . OW1 O 0.7535(4) 0.3253(2) 0.32306(17) 0.0566(8) Uani 1 1 d . . . OW2 O 0.6598(4) 0.1642(2) 0.19832(17) 0.0574(9) 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 0.0450(3) 0.0362(3) 0.0258(3) -0.0034(2) 0.0058(2) -0.0026(2) N1 0.0490(18) 0.044(2) 0.0278(17) -0.0081(15) -0.0040(14) 0.0106(16) N2 0.0357(15) 0.0391(19) 0.0290(17) -0.0056(14) -0.0017(12) 0.0004(14) N3 0.0381(16) 0.042(2) 0.0306(17) -0.0044(15) -0.0004(13) 0.0060(14) N4 0.0389(16) 0.040(2) 0.0383(19) -0.0003(15) -0.0097(13) -0.0033(15) N5 0.0393(17) 0.048(2) 0.0261(17) 0.0027(15) 0.0038(13) 0.0106(15) C1 0.062(2) 0.042(2) 0.033(2) -0.0111(19) -0.0016(18) 0.002(2) C2 0.055(2) 0.041(2) 0.039(2) -0.0031(19) 0.0056(18) 0.0015(19) C3 0.056(2) 0.033(2) 0.029(2) -0.0027(17) -0.0012(17) 0.0149(18) C4 0.058(2) 0.044(2) 0.028(2) -0.0059(18) -0.0019(17) 0.0126(19) C5 0.043(2) 0.041(2) 0.040(2) -0.0121(19) -0.0038(17) 0.0016(18) C6 0.046(2) 0.040(2) 0.040(2) 0.0043(19) 0.0095(17) 0.0023(18) C7 0.048(2) 0.047(3) 0.030(2) 0.0065(18) 0.0075(17) 0.0084(19) C8 0.053(2) 0.059(3) 0.027(2) -0.012(2) -0.0029(17) 0.006(2) C9 0.071(3) 0.045(3) 0.052(3) -0.024(2) -0.011(2) 0.007(2) C10 0.052(2) 0.041(2) 0.057(3) -0.008(2) -0.014(2) -0.002(2) C11 0.052(2) 0.044(3) 0.050(3) 0.012(2) 0.006(2) -0.004(2) C12 0.050(2) 0.051(3) 0.041(2) 0.016(2) 0.0126(18) 0.005(2) C13 0.050(2) 0.057(3) 0.025(2) -0.0046(19) -0.0044(17) 0.017(2) C14 0.035(2) 0.059(3) 0.030(2) -0.002(2) -0.0025(16) 0.0023(19) C15 0.045(2) 0.048(3) 0.032(2) 0.009(2) -0.0064(17) -0.0063(19) C16 0.0336(18) 0.054(3) 0.0272(19) 0.0057(19) 0.0003(15) 0.0033(18) C17 0.057(2) 0.042(2) 0.051(3) 0.001(2) -0.014(2) -0.009(2) C18 0.056(2) 0.046(3) 0.046(3) 0.012(2) -0.019(2) -0.006(2) C19 0.0344(18) 0.050(2) 0.0267(19) 0.0033(18) -0.0038(15) -0.0021(17) C20 0.043(2) 0.039(2) 0.028(2) 0.0005(17) -0.0007(16) 0.0011(17) C21 0.044(2) 0.043(2) 0.027(2) 0.0034(17) -0.0021(16) 0.0068(18) O1 0.0573(17) 0.063(2) 0.0353(17) 0.0130(15) -0.0139(13) -0.0061(15) O2 0.099(3) 0.064(2) 0.064(2) -0.0154(19) -0.046(2) 0.018(2) O3 0.0560(17) 0.066(2) 0.0353(17) -0.0046(16) -0.0128(14) 0.0120(16) O4 0.124(3) 0.052(2) 0.087(3) 0.025(2) -0.075(2) -0.019(2) OW1 0.0571(17) 0.069(2) 0.0434(18) 0.0005(17) -0.0001(14) 0.0022(16) OW2 0.0543(17) 0.075(2) 0.0429(18) -0.0033(17) -0.0030(14) -0.0069(16) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 N4 2.008(4) . ? Cu1 N2 2.013(3) . ? Cu1 N3 2.013(3) . ? Cu1 N5 2.020(3) . ? N1 C5 1.432(5) . ? N1 C13 1.443(6) . ? N1 C4 1.470(5) . ? N2 C6 1.471(5) . ? N2 C5 1.498(5) . ? N2 H2 0.91 . ? N3 C8 1.481(5) . ? N3 C7 1.489(5) . ? N3 H3 0.91 . ? N4 C10 1.466(5) . ? N4 C11 1.488(5) . ? N4 H4 0.91 . ? N5 C12 1.487(5) . ? N5 C13 1.496(5) . ? N5 H5 0.91 . ? C1 C3 1.375(6) . ? C1 C2 1.390(6) 3_655 ? C1 H1 0.93 . ? C2 C3 1.383(5) . ? C2 C1 1.390(6) 3_655 ? C2 H2A 0.93 . ? C3 C4 1.512(5) . ? C4 H4A 0.97 . ? C4 H4B 0.97 . ? C5 H5A 0.97 . ? C5 H5B 0.97 . ? C6 C7 1.510(6) . ? C6 H6A 0.97 . ? C6 H6B 0.97 . ? C7 H7A 0.97 . ? C7 H7B 0.97 . ? C8 C9 1.514(7) . ? C8 H8A 0.97 . ? C8 H8B 0.97 . ? C9 C10 1.519(7) . ? C9 H9A 0.97 . ? C9 H9B 0.97 . ? C10 H10A 0.97 . ? C10 H10B 0.97 . ? C11 C12 1.527(6) . ? C11 H11A 0.97 . ? C11 H11B 0.97 . ? C12 H12A 0.97 . ? C12 H12B 0.97 . ? C13 H13A 0.97 . ? C13 H13B 0.97 . ? C14 O2 1.245(6) . ? C14 O1 1.273(5) . ? C14 C16 1.519(5) . ? C15 O4 1.222(5) . ? C15 O3 1.248(5) . ? C15 C19 1.534(5) . ? C16 C17 1.385(6) . ? C16 C21 1.387(6) . ? C17 C18 1.387(6) . ? C17 H17 0.93 . ? C18 C19 1.380(6) . ? C18 H18 0.93 . ? C19 C20 1.382(6) . ? C20 C21 1.392(5) . ? C20 H20 0.93 . ? C21 H21 0.93 . ? 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 N4 Cu1 N2 174.73(12) . . ? N4 Cu1 N3 94.27(14) . . ? N2 Cu1 N3 85.10(13) . . ? N4 Cu1 N5 86.21(14) . . ? N2 Cu1 N5 93.99(13) . . ? N3 Cu1 N5 175.34(12) . . ? C5 N1 C13 115.5(3) . . ? C5 N1 C4 115.5(3) . . ? C13 N1 C4 115.8(3) . . ? C6 N2 C5 111.7(3) . . ? C6 N2 Cu1 108.8(2) . . ? C5 N2 Cu1 115.5(3) . . ? C6 N2 H2 106.8 . . ? C5 N2 H2 106.8 . . ? Cu1 N2 H2 106.8 . . ? C8 N3 C7 112.5(3) . . ? C8 N3 Cu1 116.4(3) . . ? C7 N3 Cu1 107.1(2) . . ? C8 N3 H3 106.8 . . ? C7 N3 H3 106.8 . . ? Cu1 N3 H3 106.8 . . ? C10 N4 C11 112.7(3) . . ? C10 N4 Cu1 118.0(3) . . ? C11 N4 Cu1 107.4(3) . . ? C10 N4 H4 106 . . ? C11 N4 H4 106 . . ? Cu1 N4 H4 106 . . ? C12 N5 C13 111.8(3) . . ? C12 N5 Cu1 107.5(3) . . ? C13 N5 Cu1 115.5(2) . . ? C12 N5 H5 107.2 . . ? C13 N5 H5 107.2 . . ? Cu1 N5 H5 107.2 . . ? C3 C1 C2 121.2(4) . 3_655 ? C3 C1 H1 119.4 . . ? C2 C1 H1 119.4 3_655 . ? C3 C2 C1 120.9(4) . 3_655 ? C3 C2 H2A 119.5 . . ? C1 C2 H2A 119.5 3_655 . ? C1 C3 C2 117.9(4) . . ? C1 C3 C4 121.6(4) . . ? C2 C3 C4 120.5(4) . . ? N1 C4 C3 111.9(3) . . ? N1 C4 H4A 109.2 . . ? C3 C4 H4A 109.2 . . ? N1 C4 H4B 109.2 . . ? C3 C4 H4B 109.2 . . ? H4A C4 H4B 107.9 . . ? N1 C5 N2 115.3(3) . . ? N1 C5 H5A 108.5 . . ? N2 C5 H5A 108.5 . . ? N1 C5 H5B 108.5 . . ? N2 C5 H5B 108.5 . . ? H5A C5 H5B 107.5 . . ? N2 C6 C7 107.9(3) . . ? N2 C6 H6A 110.1 . . ? C7 C6 H6A 110.1 . . ? N2 C6 H6B 110.1 . . ? C7 C6 H6B 110.1 . . ? H6A C6 H6B 108.4 . . ? N3 C7 C6 107.3(3) . . ? N3 C7 H7A 110.3 . . ? C6 C7 H7A 110.3 . . ? N3 C7 H7B 110.3 . . ? C6 C7 H7B 110.3 . . ? H7A C7 H7B 108.5 . . ? N3 C8 C9 111.2(3) . . ? N3 C8 H8A 109.4 . . ? C9 C8 H8A 109.4 . . ? N3 C8 H8B 109.4 . . ? C9 C8 H8B 109.4 . . ? H8A C8 H8B 108 . . ? C8 C9 C10 115.5(4) . . ? C8 C9 H9A 108.4 . . ? C10 C9 H9A 108.4 . . ? C8 C9 H9B 108.4 . . ? C10 C9 H9B 108.4 . . ? H9A C9 H9B 107.5 . . ? N4 C10 C9 112.1(3) . . ? N4 C10 H10A 109.2 . . ? C9 C10 H10A 109.2 . . ? N4 C10 H10B 109.2 . . ? C9 C10 H10B 109.2 . . ? H10A C10 H10B 107.9 . . ? N4 C11 C12 107.5(3) . . ? N4 C11 H11A 110.2 . . ? C12 C11 H11A 110.2 . . ? N4 C11 H11B 110.2 . . ? C12 C11 H11B 110.2 . . ? H11A C11 H11B 108.5 . . ? N5 C12 C11 108.5(3) . . ? N5 C12 H12A 110 . . ? C11 C12 H12A 110 . . ? N5 C12 H12B 110 . . ? C11 C12 H12B 110 . . ? H12A C12 H12B 108.4 . . ? N1 C13 N5 115.3(3) . . ? N1 C13 H13A 108.5 . . ? N5 C13 H13A 108.5 . . ? N1 C13 H13B 108.5 . . ? N5 C13 H13B 108.5 . . ? H13A C13 H13B 107.5 . . ? O2 C14 O1 124.3(4) . . ? O2 C14 C16 118.0(4) . . ? O1 C14 C16 117.7(4) . . ? O4 C15 O3 123.8(4) . . ? O4 C15 C19 117.8(4) . . ? O3 C15 C19 118.4(4) . . ? C17 C16 C21 118.7(4) . . ? C17 C16 C14 119.7(4) . . ? C21 C16 C14 121.6(4) . . ? C16 C17 C18 120.7(4) . . ? C16 C17 H17 119.6 . . ? C18 C17 H17 119.6 . . ? C19 C18 C17 120.5(4) . . ? C19 C18 H18 119.8 . . ? C17 C18 H18 119.8 . . ? C18 C19 C20 119.2(3) . . ? C18 C19 C15 120.7(4) . . ? C20 C19 C15 120.2(4) . . ? C19 C20 C21 120.5(4) . . ? C19 C20 H20 119.8 . . ? C21 C20 H20 119.8 . . ? C16 C21 C20 120.4(4) . . ? C16 C21 H21 119.8 . . ? C20 C21 H21 119.8 . . ? #============================================================================== data_2 _database_code_depnum_ccdc_archive 'CCDC 747626' #TrackingRef 'CCDC 747626.cif' #============================================================================== _audit_creation_date 2011-12-12T08:52:42-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C27 H40 Cu N5 O8' _chemical_formula_sum 'C54 H80 Cu2 N10 O16' _chemical_formula_weight 1252.36 #----------------------------------------------------------------------------# # 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 11.0014(4) _cell_length_b 16.1868(6) _cell_length_c 17.8272(7) _cell_angle_alpha 90 _cell_angle_beta 106.526(2) _cell_angle_gamma 90 _cell_volume 3043.5(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6105 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.103 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.367 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1320 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.772 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_av_R_equivalents 0.1264 _diffrn_reflns_av_unetI/netI 0.1734 _diffrn_reflns_number 11902 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 27.26 _diffrn_reflns_theta_full 27.26 _diffrn_measured_fraction_theta_full 0.951 _diffrn_measured_fraction_theta_max 0.951 _reflns_number_total 6490 _reflns_number_gt 2822 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _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, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # 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^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1434P)^2^+2.2673P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 6490 _refine_ls_number_parameters 372 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2395 _refine_ls_R_factor_gt 0.0884 _refine_ls_wR_factor_ref 0.3108 _refine_ls_wR_factor_gt 0.223 _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_restrained_S_all 1.099 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.811 _refine_diff_density_min -1.199 _refine_diff_density_rms 0.302 #----------------------------------------------------------------------------# # 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' N N 0.0061 0.0033 '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' H H 0 0 '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' 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 0.24459(7) -0.28192(6) -0.26346(5) 0.0462(4) Uani 1 1 d . . . N1 N 0.2924(6) -0.4284(4) -0.3827(3) 0.0593(18) Uani 1 1 d . . . N2 N 0.3333(5) -0.2806(4) -0.3483(3) 0.0469(15) Uani 1 1 d . . . H2 H 0.4169 -0.2906 -0.3249 0.056 Uiso 1 1 calc R . . N3 N 0.2481(5) -0.1565(4) -0.2689(3) 0.0507(16) Uani 1 1 d . . . H3 H 0.1703 -0.1408 -0.2994 0.061 Uiso 1 1 calc R . . N4 N 0.1501(5) -0.2833(4) -0.1821(3) 0.0476(16) Uani 1 1 d . . . H4 H 0.067 -0.2761 -0.2086 0.057 Uiso 1 1 calc R . . N5 N 0.2361(4) -0.4064(4) -0.2608(3) 0.0445(15) Uani 1 1 d . . . H5 H 0.3132 -0.4251 -0.2319 0.053 Uiso 1 1 calc R . . C1 C 0.6139(7) -0.4693(5) -0.5046(5) 0.058(2) Uani 1 1 d . . . H1 H 0.6909 -0.4478 -0.5074 0.069 Uiso 1 1 calc R . . C2 C 0.5749(7) -0.4550(5) -0.4394(5) 0.059(2) Uani 1 1 d . . . H2A H 0.6267 -0.4248 -0.3982 0.071 Uiso 1 1 calc R . . C3 C 0.4600(7) -0.4845(5) -0.4335(4) 0.0512(19) Uani 1 1 d . . . C4 C 0.4187(7) -0.4693(5) -0.3617(4) 0.063(2) Uani 1 1 d . . . H4A H 0.4141 -0.5214 -0.3357 0.075 Uiso 1 1 calc R . . H4B H 0.4804 -0.4345 -0.3258 0.075 Uiso 1 1 calc R . . C5 C 0.2882(7) -0.3443(5) -0.4101(4) 0.055(2) Uani 1 1 d . . . H5A H 0.2015 -0.3313 -0.4391 0.066 Uiso 1 1 calc R . . H5B H 0.3393 -0.3405 -0.4463 0.066 Uiso 1 1 calc R . . C6 C 0.3232(8) -0.1950(5) -0.3795(5) 0.064(2) Uani 1 1 d . . . H6A H 0.2412 -0.1871 -0.4175 0.077 Uiso 1 1 calc R . . H6B H 0.3885 -0.1855 -0.4053 0.077 Uiso 1 1 calc R . . C7 C 0.3385(7) -0.1353(5) -0.3129(5) 0.065(2) Uani 1 1 d . . . H7A H 0.4245 -0.138 -0.2786 0.078 Uiso 1 1 calc R . . H7B H 0.3229 -0.0794 -0.333 0.078 Uiso 1 1 calc R . . C8 C 0.2685(9) -0.1123(5) -0.1937(5) 0.073(2) Uani 1 1 d . . . H8A H 0.2657 -0.0533 -0.2034 0.087 Uiso 1 1 calc R . . H8B H 0.3522 -0.1256 -0.1601 0.087 Uiso 1 1 calc R . . C9 C 0.1716(8) -0.1338(6) -0.1520(5) 0.072(3) Uani 1 1 d . . . H9A H 0.1811 -0.0958 -0.1086 0.086 Uiso 1 1 calc R . . H9B H 0.0878 -0.1255 -0.1877 0.086 Uiso 1 1 calc R . . C10 C 0.1797(8) -0.2202(6) -0.1211(4) 0.068(3) Uani 1 1 d . . . H10A H 0.2648 -0.2297 -0.0874 0.081 Uiso 1 1 calc R . . H10B H 0.1216 -0.2259 -0.0895 0.081 Uiso 1 1 calc R . . C11 C 0.1610(6) -0.3693(5) -0.1512(4) 0.054(2) Uani 1 1 d . . . H11A H 0.2437 -0.3776 -0.1141 0.065 Uiso 1 1 calc R . . H11B H 0.0968 -0.3793 -0.1246 0.065 Uiso 1 1 calc R . . C12 C 0.1435(6) -0.4271(5) -0.2181(4) 0.052(2) Uani 1 1 d . . . H12A H 0.1562 -0.4835 -0.1992 0.062 Uiso 1 1 calc R . . H12B H 0.058 -0.4223 -0.2527 0.062 Uiso 1 1 calc R . . C13 C 0.2050(7) -0.4488(6) -0.3391(4) 0.061(2) Uani 1 1 d . . . H13A H 0.2059 -0.5081 -0.3312 0.073 Uiso 1 1 calc R . . H13B H 0.1201 -0.4332 -0.3693 0.073 Uiso 1 1 calc R . . C14 C 0.9321(7) -0.2275(5) 0.1341(4) 0.0476(19) Uani 1 1 d . . . C15 C 0.5484(6) -0.2698(4) -0.1660(4) 0.048(2) Uani 1 1 d . . . C16 C 0.8300(6) -0.2303(4) 0.0561(4) 0.0439(18) Uani 1 1 d . . . C17 C 0.8596(7) -0.2199(5) -0.0111(4) 0.057(2) Uani 1 1 d . . . H17 H 0.9422 -0.2054 -0.0094 0.069 Uiso 1 1 calc R . . C18 C 0.7691(7) -0.2303(5) -0.0842(4) 0.059(2) Uani 1 1 d . . . H18 H 0.7921 -0.2241 -0.1302 0.07 Uiso 1 1 calc R . . C19 C 0.6454(6) -0.2499(5) -0.0869(4) 0.0483(18) Uani 1 1 d . . . C20 C 0.6137(7) -0.2564(5) -0.0192(4) 0.056(2) Uani 1 1 d . . . H20 H 0.5301 -0.268 -0.0209 0.067 Uiso 1 1 calc R . . C21 C 0.7031(6) -0.2463(5) 0.0526(4) 0.053(2) Uani 1 1 d . . . H21 H 0.6791 -0.2502 0.0984 0.064 Uiso 1 1 calc R . . C22 C 0.4241(7) 0.0248(5) -0.4556(5) 0.065(2) Uani 1 1 d . . . H22 H 0.3722 0.0421 -0.4256 0.078 Uiso 1 1 calc R . . C23 C 0.5370(7) -0.0128(5) -0.4209(4) 0.058(2) Uani 1 1 d . . . C24 C 0.6126(7) -0.0372(5) -0.4651(5) 0.065(2) Uani 1 1 d . . . H24 H 0.69 -0.0624 -0.4413 0.078 Uiso 1 1 calc R . . C25 C -0.0758(8) -0.4375(6) -0.0397(6) 0.072(3) Uani 1 1 d . . . H25 H -0.1267 -0.3946 -0.0659 0.086 Uiso 1 1 calc R . . C26 C -0.0489(7) -0.5026(5) -0.0814(5) 0.062(2) Uani 1 1 d . . . C27 C 0.0275(8) -0.5653(5) -0.0419(5) 0.069(2) Uani 1 1 d . . . H27 H 0.0471 -0.6097 -0.0695 0.083 Uiso 1 1 calc R . . O1 O 1.0415(5) -0.2183(4) 0.1319(3) 0.0632(16) Uani 1 1 d . . . O2 O 0.8995(4) -0.2382(4) 0.1963(3) 0.0602(15) Uani 1 1 d . . . O3 O 0.4374(5) -0.2830(4) -0.1626(3) 0.0699(17) Uani 1 1 d . . . O4 O 0.5855(5) -0.2711(4) -0.2266(3) 0.0642(16) Uani 1 1 d . . . O5 O 0.5702(5) -0.0246(4) -0.3397(3) 0.0639(15) Uani 1 1 d . . . H5C H 0.6254 -0.0602 -0.3271 0.096 Uiso 1 1 calc R . . O6 O -0.0904(6) -0.5088(4) -0.1620(3) 0.0758(17) Uani 1 1 d . . . H6 H -0.1337 -0.4683 -0.18 0.114 Uiso 1 1 calc R . . O1W O 0.2750(5) -0.6501(4) -0.2268(3) 0.0697(16) Uani 1 1 d . . . O2W O 0.7761(5) -0.3795(4) -0.2392(3) 0.0754(17) 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 0.0391(5) 0.0626(7) 0.0363(5) 0.0012(4) 0.0098(4) -0.0009(4) N1 0.059(4) 0.070(5) 0.048(4) -0.005(3) 0.014(3) 0.007(3) N2 0.033(3) 0.059(4) 0.046(4) 0.012(3) 0.007(3) 0.008(3) N3 0.048(3) 0.048(4) 0.050(4) 0.006(3) 0.004(3) -0.003(3) N4 0.036(3) 0.067(4) 0.036(3) -0.007(3) 0.004(2) -0.005(3) N5 0.031(3) 0.065(4) 0.041(3) 0.009(3) 0.016(2) 0.005(3) C1 0.062(5) 0.049(5) 0.070(5) -0.007(4) 0.033(4) -0.016(4) C2 0.061(5) 0.063(6) 0.057(5) -0.007(4) 0.025(4) -0.003(4) C3 0.069(5) 0.045(5) 0.042(4) -0.006(4) 0.020(4) -0.002(4) C4 0.062(5) 0.063(6) 0.059(5) 0.002(4) 0.011(4) 0.011(4) C5 0.046(4) 0.082(7) 0.037(4) 0.001(4) 0.013(3) 0.010(4) C6 0.054(5) 0.074(6) 0.065(6) 0.034(5) 0.016(4) 0.008(4) C7 0.049(5) 0.062(6) 0.087(6) 0.006(5) 0.022(4) 0.007(4) C8 0.102(7) 0.051(6) 0.060(5) -0.007(4) 0.016(5) -0.011(5) C9 0.085(6) 0.067(7) 0.057(5) -0.018(5) 0.011(5) 0.003(5) C10 0.065(5) 0.097(8) 0.039(5) -0.012(5) 0.012(4) -0.008(5) C11 0.040(4) 0.084(7) 0.041(4) 0.012(4) 0.016(3) -0.006(4) C12 0.047(4) 0.069(5) 0.042(4) 0.001(4) 0.018(3) 0.001(4) C13 0.058(5) 0.071(6) 0.059(5) -0.006(4) 0.024(4) 0.002(4) C14 0.042(4) 0.058(5) 0.041(4) 0.001(4) 0.009(3) -0.003(4) C15 0.031(4) 0.047(5) 0.054(5) 0.017(4) -0.005(3) 0.001(3) C16 0.026(4) 0.060(5) 0.039(4) -0.004(3) 0.000(3) -0.001(3) C17 0.032(4) 0.089(6) 0.049(5) -0.011(4) 0.008(3) -0.011(4) C18 0.045(4) 0.084(6) 0.044(5) 0.006(4) 0.009(4) 0.002(4) C19 0.033(4) 0.061(5) 0.045(4) -0.001(4) 0.002(3) 0.001(3) C20 0.027(4) 0.083(6) 0.055(5) -0.006(4) 0.005(3) 0.005(4) C21 0.040(4) 0.076(5) 0.040(4) 0.008(4) 0.006(3) -0.001(4) C22 0.062(5) 0.076(6) 0.061(5) 0.005(5) 0.023(4) 0.019(4) C23 0.061(5) 0.053(5) 0.055(5) 0.004(4) 0.010(4) -0.007(4) C24 0.054(5) 0.071(6) 0.063(5) 0.006(5) 0.007(4) 0.015(4) C25 0.064(5) 0.061(6) 0.084(7) 0.008(5) 0.012(5) 0.007(5) C26 0.046(4) 0.051(6) 0.089(6) 0.002(5) 0.019(4) -0.007(4) C27 0.072(6) 0.056(6) 0.077(6) -0.005(5) 0.018(5) 0.003(5) O1 0.035(3) 0.104(5) 0.044(3) -0.005(3) 0.001(2) -0.020(3) O2 0.040(3) 0.094(4) 0.045(3) 0.001(3) 0.009(2) -0.010(3) O3 0.037(3) 0.114(5) 0.052(3) 0.011(3) 0.000(2) -0.001(3) O4 0.051(3) 0.099(5) 0.041(3) 0.007(3) 0.010(3) -0.002(3) O5 0.063(3) 0.071(4) 0.054(3) 0.004(3) 0.011(3) 0.006(3) O6 0.074(4) 0.071(4) 0.074(4) 0.011(3) 0.008(3) 0.001(3) O1W 0.084(4) 0.071(4) 0.053(3) -0.007(3) 0.018(3) -0.021(3) O2W 0.076(4) 0.075(4) 0.077(4) 0.015(3) 0.025(3) 0.010(3) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 N4 2.010(6) . ? Cu1 N5 2.019(6) . ? Cu1 N2 2.019(6) . ? Cu1 N3 2.033(6) . ? Cu1 O3 2.359(5) . ? N1 C13 1.436(10) . ? N1 C5 1.444(10) . ? N1 C4 1.488(9) . ? N2 C6 1.484(10) . ? N2 C5 1.488(9) . ? N3 C7 1.472(9) . ? N3 C8 1.480(10) . ? N4 C10 1.460(9) . ? N4 C11 1.490(10) . ? N5 C12 1.472(8) . ? N5 C13 1.504(9) . ? C1 C2 1.369(10) . ? C1 C3 1.389(10) 3_644 ? C2 C3 1.382(10) . ? C3 C1 1.389(10) 3_644 ? C3 C4 1.495(10) . ? C6 C7 1.503(12) . ? C8 C9 1.504(12) . ? C9 C10 1.495(12) . ? C11 C12 1.485(10) . ? C14 O1 1.225(8) . ? C14 O2 1.270(9) . ? C14 C16 1.518(9) . ? C15 O3 1.257(9) . ? C15 O4 1.260(9) . ? C15 C19 1.541(9) . ? C16 C17 1.339(10) . ? C16 C21 1.404(10) . ? C17 C18 1.407(10) . ? C18 C19 1.385(10) . ? C19 C20 1.352(10) . ? C20 C21 1.383(10) . ? C22 C23 1.364(11) . ? C22 C24 1.370(11) 3_654 ? C23 C24 1.356(11) . ? C23 O5 1.402(9) . ? C24 C22 1.370(11) 3_654 ? C25 C26 1.370(12) . ? C25 C27 1.400(11) 3_545 ? C26 C27 1.377(11) . ? C26 O6 1.380(10) . ? C27 C25 1.400(11) 3_545 ? 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 N4 Cu1 N5 86.3(2) . . ? N4 Cu1 N2 177.9(2) . . ? N5 Cu1 N2 93.7(2) . . ? N4 Cu1 N3 93.8(2) . . ? N5 Cu1 N3 178.2(2) . . ? N2 Cu1 N3 86.2(2) . . ? N4 Cu1 O3 89.3(2) . . ? N5 Cu1 O3 90.7(2) . . ? N2 Cu1 O3 92.8(2) . . ? N3 Cu1 O3 91.1(2) . . ? C13 N1 C5 116.0(6) . . ? C13 N1 C4 118.9(6) . . ? C5 N1 C4 116.3(6) . . ? C6 N2 C5 113.3(6) . . ? C6 N2 Cu1 106.9(5) . . ? C5 N2 Cu1 114.6(5) . . ? C7 N3 C8 114.7(6) . . ? C7 N3 Cu1 106.5(5) . . ? C8 N3 Cu1 116.1(5) . . ? C10 N4 C11 113.7(6) . . ? C10 N4 Cu1 118.6(5) . . ? C11 N4 Cu1 105.9(4) . . ? C12 N5 C13 111.6(6) . . ? C12 N5 Cu1 106.4(4) . . ? C13 N5 Cu1 115.7(5) . . ? C2 C1 C3 120.8(7) . 3_644 ? C1 C2 C3 121.4(7) . . ? C2 C3 C1 117.8(7) . 3_644 ? C2 C3 C4 121.0(7) . . ? C1 C3 C4 121.2(7) 3_644 . ? N1 C4 C3 110.3(6) . . ? N1 C5 N2 115.6(6) . . ? N2 C6 C7 108.9(6) . . ? N3 C7 C6 109.2(7) . . ? N3 C8 C9 113.0(7) . . ? C10 C9 C8 114.9(8) . . ? N4 C10 C9 113.8(6) . . ? C12 C11 N4 108.2(5) . . ? N5 C12 C11 108.8(6) . . ? N1 C13 N5 112.8(6) . . ? O1 C14 O2 124.6(6) . . ? O1 C14 C16 116.9(7) . . ? O2 C14 C16 118.4(6) . . ? O3 C15 O4 126.5(6) . . ? O3 C15 C19 114.9(7) . . ? O4 C15 C19 118.7(6) . . ? C17 C16 C21 118.4(6) . . ? C17 C16 C14 120.7(6) . . ? C21 C16 C14 120.9(7) . . ? C16 C17 C18 121.7(7) . . ? C19 C18 C17 119.3(7) . . ? C20 C19 C18 119.2(6) . . ? C20 C19 C15 120.9(6) . . ? C18 C19 C15 119.8(7) . . ? C19 C20 C21 121.3(7) . . ? C20 C21 C16 120.0(7) . . ? C23 C22 C24 119.8(8) . 3_654 ? C24 C23 C22 119.7(7) . . ? C24 C23 O5 122.5(7) . . ? C22 C23 O5 117.8(8) . . ? C23 C24 C22 120.5(7) . 3_654 ? C26 C25 C27 120.8(8) . 3_545 ? C25 C26 C27 118.9(8) . . ? C25 C26 O6 124.2(8) . . ? C27 C26 O6 116.9(8) . . ? C26 C27 C25 120.3(8) . 3_545 ? C15 O3 Cu1 129.6(5) . . ? #============================================================================== data_3 _database_code_depnum_ccdc_archive 'CCDC 747627' #TrackingRef 'CCDC 747627.cif' #============================================================================== _audit_creation_date 2011-12-12T09:31:47-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C33 H46 Cu N5 O8' _chemical_formula_sum 'C66 H92 Cu2 N10 O16' _chemical_formula_weight 1408.58 #----------------------------------------------------------------------------# # 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 10.4604(5) _cell_length_b 11.9640(7) _cell_length_c 16.1087(8) _cell_angle_alpha 78.673(3) _cell_angle_beta 72.493(3) _cell_angle_gamma 64.513(3) _cell_volume 1730.24(16) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.352 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.687 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_av_R_equivalents 0.0321 _diffrn_reflns_av_unetI/netI 0.0778 _diffrn_reflns_number 11371 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.33 _diffrn_reflns_theta_max 27.52 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.989 _diffrn_measured_fraction_theta_max 0.989 _reflns_number_total 7888 _reflns_number_gt 4819 _reflns_threshold_expression >2sigma(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-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # 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^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1255P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 7888 _refine_ls_number_parameters 426 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1203 _refine_ls_R_factor_gt 0.0616 _refine_ls_wR_factor_ref 0.2233 _refine_ls_wR_factor_gt 0.1748 _refine_ls_goodness_of_fit_ref 1.101 _refine_ls_restrained_S_all 1.101 _refine_ls_shift/su_max 0.04 _refine_ls_shift/su_mean 0.001 _refine_diff_density_max 0.907 _refine_diff_density_min -1.091 _refine_diff_density_rms 0.237 #----------------------------------------------------------------------------# # 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 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' 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' O O 0.0106 0.006 '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 0.23660(4) 0.32366(4) 0.23844(3) 0.03740(19) Uani 1 1 d . . . N1 N 0.2445(4) 0.4482(3) 0.4037(2) 0.0483(8) Uani 1 1 d . . . N2 N 0.1652(3) 0.3001(3) 0.36836(19) 0.0413(8) Uani 1 1 d . . . H2 H 0.2371 0.234 0.3882 0.05 Uiso 1 1 calc R . . N3 N 0.1120(4) 0.2378(3) 0.2303(2) 0.0471(8) Uani 1 1 d . . . H3 H 0.0275 0.2982 0.2194 0.057 Uiso 1 1 calc R . . N4 N 0.3047(3) 0.3519(3) 0.10842(19) 0.0407(7) Uani 1 1 d . . . H4 H 0.231 0.4196 0.0914 0.049 Uiso 1 1 calc R . . N5 N 0.3540(3) 0.4160(3) 0.24711(19) 0.0396(7) Uani 1 1 d . . . H5 H 0.4391 0.3578 0.2588 0.047 Uiso 1 1 calc R . . C1 C 0.3666(5) 0.5653(4) 0.4825(3) 0.0532(11) Uani 1 1 d . . . H1 H 0.2753 0.6109 0.4708 0.064 Uiso 1 1 calc R . . C2 C 0.5680(5) 0.3746(4) 0.4910(3) 0.0559(12) Uani 1 1 d . . . H2A H 0.6155 0.2895 0.4853 0.067 Uiso 1 1 calc R . . C3 C 0.4323(5) 0.4389(4) 0.4725(2) 0.0511(11) Uani 1 1 d . . . C4 C 0.3637(5) 0.3676(4) 0.4469(3) 0.0545(11) Uani 1 1 d . . . H4A H 0.4382 0.3062 0.4076 0.065 Uiso 1 1 calc R . . H4B H 0.3252 0.3238 0.4987 0.065 Uiso 1 1 calc R . . C5 C 0.1292(5) 0.4081(4) 0.4167(3) 0.0520(11) Uani 1 1 d . . . H5A H 0.047 0.4773 0.3997 0.062 Uiso 1 1 calc R . . H5B H 0.0982 0.3868 0.4786 0.062 Uiso 1 1 calc R . . C6 C 0.0386(5) 0.2657(4) 0.3839(3) 0.0600(12) Uani 1 1 d . . . H6A H -0.0482 0.3394 0.3781 0.072 Uiso 1 1 calc R . . H6B H 0.0202 0.2266 0.4425 0.072 Uiso 1 1 calc R . . C7 C 0.0738(5) 0.1775(4) 0.3180(3) 0.0574(12) Uani 1 1 d . . . H7A H 0.1551 0.1006 0.3272 0.069 Uiso 1 1 calc R . . H7B H -0.0099 0.1585 0.3236 0.069 Uiso 1 1 calc R . . C8 C 0.1743(5) 0.1500(4) 0.1612(3) 0.0653(13) Uani 1 1 d . . . H8A H 0.1041 0.1166 0.1622 0.078 Uiso 1 1 calc R . . H8B H 0.2615 0.0814 0.1729 0.078 Uiso 1 1 calc R . . C9 C 0.2127(6) 0.2130(5) 0.0709(3) 0.0691(13) Uani 1 1 d . . . H9A H 0.2369 0.1564 0.0276 0.083 Uiso 1 1 calc R . . H9B H 0.1267 0.2856 0.062 0.083 Uiso 1 1 calc R . . C10 C 0.3373(4) 0.2529(4) 0.0545(3) 0.0546(11) Uani 1 1 d . . . H10A H 0.4226 0.1816 0.066 0.066 Uiso 1 1 calc R . . H10B H 0.361 0.2816 -0.0066 0.066 Uiso 1 1 calc R . . C11 C 0.4272(4) 0.3889(4) 0.0927(3) 0.0530(11) Uani 1 1 d . . . H11A H 0.4432 0.4293 0.0344 0.064 Uiso 1 1 calc R . . H11B H 0.5155 0.3161 0.0974 0.064 Uiso 1 1 calc R . . C12 C 0.3923(5) 0.4765(4) 0.1591(3) 0.0521(11) Uani 1 1 d . . . H12A H 0.4761 0.4952 0.1535 0.063 Uiso 1 1 calc R . . H12B H 0.3111 0.5535 0.1501 0.063 Uiso 1 1 calc R . . C13 C 0.2861(5) 0.5043(4) 0.3167(3) 0.0513(11) Uani 1 1 d . . . H13A H 0.3545 0.539 0.3169 0.062 Uiso 1 1 calc R . . H13B H 0.2 0.5722 0.3029 0.062 Uiso 1 1 calc R . . C15 C -0.5050(5) 1.0615(4) 0.2924(3) 0.0541(11) Uani 1 1 d . . . C14 C -0.0135(4) 0.5991(4) 0.1856(3) 0.0445(9) Uani 1 1 d . . . C16 C -0.1436(4) 0.7185(3) 0.2124(2) 0.0409(9) Uani 1 1 d . . . C17 C -0.2248(5) 0.7291(4) 0.2979(3) 0.0568(12) Uani 1 1 d . . . H17 H -0.2006 0.6609 0.3383 0.068 Uiso 1 1 calc R . . C18 C -0.3408(5) 0.8383(4) 0.3255(3) 0.0562(12) Uani 1 1 d . . . H18 H -0.3919 0.844 0.3838 0.067 Uiso 1 1 calc R . . C19 C -0.3798(4) 0.9391(3) 0.2649(3) 0.0458(10) Uani 1 1 d . . . C20 C -0.3019(4) 0.9295(4) 0.1795(3) 0.0493(11) Uani 1 1 d . . . H20 H -0.3281 0.9969 0.1389 0.059 Uiso 1 1 calc R . . C21 C -0.1845(4) 0.8201(4) 0.1531(3) 0.0504(11) Uani 1 1 d . . . H21 H -0.1326 0.815 0.0949 0.06 Uiso 1 1 calc R . . C22 C 0.1593(14) 0.8538(6) 0.3211(5) 0.130(4) Uani 1 1 d . . . C23 C 0.0802(9) 0.8651(6) 0.2607(6) 0.096(2) Uani 1 1 d . . . H23 H -0.0203 0.8878 0.2788 0.116 Uiso 1 1 calc R . . C24 C 0.1476(10) 0.8440(6) 0.1802(6) 0.106(2) Uani 1 1 d . . . H24 H 0.0925 0.8497 0.1425 0.128 Uiso 1 1 calc R . . C25 C 0.2951(10) 0.8137(7) 0.1458(7) 0.127(3) Uani 1 1 d . . . H25 H 0.3395 0.8 0.0872 0.152 Uiso 1 1 calc R . . C26 C 0.3709(11) 0.8053(7) 0.2034(8) 0.139(4) Uani 1 1 d . . . H26 H 0.4703 0.7871 0.1825 0.167 Uiso 1 1 calc R . . C27 C 0.3130(10) 0.8213(7) 0.2870(8) 0.124(3) Uani 1 1 d . . . H27 H 0.3714 0.8117 0.3237 0.149 Uiso 1 1 calc R . . C28 C 0.8150(5) 0.3075(5) 0.0966(3) 0.0668(13) Uani 1 1 d . . . C29 C 0.7755(6) 0.2377(6) 0.1736(4) 0.0877(19) Uani 1 1 d . . . H29 H 0.7826 0.1582 0.1712 0.105 Uiso 1 1 calc R . . C30 C 0.7252(6) 0.2902(10) 0.2543(4) 0.104(3) Uani 1 1 d . . . H30 H 0.7016 0.2435 0.3053 0.125 Uiso 1 1 calc R . . C31 C 0.7105(7) 0.4050(11) 0.2595(5) 0.112(3) Uani 1 1 d . . . H31 H 0.6769 0.4381 0.3133 0.135 Uiso 1 1 calc R . . C32 C 0.7458(5) 0.4738(6) 0.1842(4) 0.0822(17) Uani 1 1 d . . . H32 H 0.7333 0.5548 0.1873 0.099 Uiso 1 1 calc R . . C33 C 0.7992(5) 0.4254(5) 0.1043(3) 0.0646(13) Uani 1 1 d . . . H33 H 0.825 0.4733 0.0546 0.078 Uiso 1 1 calc R . . O3 O -0.5484(3) 1.1410(3) 0.2330(2) 0.0649(9) Uani 1 1 d . . . O4 O -0.5635(4) 1.0730(3) 0.3732(2) 0.0962(15) Uani 1 1 d . . . O1 O 0.0174(3) 0.5134(2) 0.24296(19) 0.0550(8) Uani 1 1 d . . . O2 O 0.0545(3) 0.5934(3) 0.10640(18) 0.0646(10) Uani 1 1 d . . . O5 O 0.0861(12) 0.8774(7) 0.4019(4) 0.206(4) Uani 1 1 d . . . H5C H 0.1286 0.9024 0.4244 0.31 Uiso 1 1 calc R . . O6 O 0.8652(5) 0.2563(3) 0.0194(2) 0.0899(12) Uani 1 1 d . . . H6 H 0.8368 0.3102 -0.0188 0.135 Uiso 1 1 calc R . . O1W O 0.3814(12) 0.9567(8) 0.5243(5) 0.213(3) Uani 1 1 d . . . O2W O 0.1902(18) 0.9558(10) 0.5177(8) 0.351(8) 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 0.0404(3) 0.0311(3) 0.0370(3) -0.00507(18) -0.00552(19) -0.01237(19) N1 0.065(2) 0.0397(18) 0.0396(17) -0.0076(14) -0.0168(16) -0.0157(16) N2 0.0402(16) 0.0338(16) 0.0392(16) -0.0059(13) -0.0072(13) -0.0052(13) N3 0.0456(17) 0.0377(17) 0.055(2) -0.0024(15) -0.0144(15) -0.0126(14) N4 0.0391(16) 0.0365(16) 0.0381(16) -0.0044(13) -0.0124(13) -0.0048(13) N5 0.0429(16) 0.0355(16) 0.0385(16) 0.0015(13) -0.0151(13) -0.0123(13) C1 0.055(2) 0.040(2) 0.052(2) -0.0110(19) -0.023(2) 0.0020(19) C2 0.076(3) 0.035(2) 0.051(2) -0.0104(18) -0.031(2) -0.003(2) C3 0.071(3) 0.037(2) 0.0351(19) -0.0082(17) -0.0201(19) -0.0055(19) C4 0.070(3) 0.038(2) 0.051(2) -0.0034(18) -0.028(2) -0.010(2) C5 0.055(2) 0.039(2) 0.044(2) -0.0144(18) -0.0047(19) -0.0026(19) C6 0.059(3) 0.053(3) 0.057(3) 0.004(2) 0.000(2) -0.026(2) C7 0.057(2) 0.043(2) 0.073(3) 0.004(2) -0.015(2) -0.025(2) C8 0.071(3) 0.054(3) 0.088(4) -0.020(3) -0.029(3) -0.028(2) C9 0.078(3) 0.066(3) 0.069(3) -0.024(3) -0.033(3) -0.017(3) C10 0.053(2) 0.055(3) 0.046(2) -0.017(2) -0.0103(19) -0.008(2) C11 0.048(2) 0.061(3) 0.043(2) 0.002(2) -0.0073(18) -0.021(2) C12 0.058(2) 0.058(3) 0.050(2) 0.006(2) -0.015(2) -0.036(2) C13 0.072(3) 0.033(2) 0.052(2) -0.0013(18) -0.029(2) -0.0156(19) C15 0.052(2) 0.029(2) 0.061(3) -0.0092(19) -0.022(2) 0.0098(17) C14 0.0379(19) 0.035(2) 0.053(2) -0.0075(18) -0.0158(18) -0.0028(16) C16 0.0384(19) 0.0329(19) 0.047(2) -0.0072(16) -0.0158(16) -0.0048(15) C17 0.058(2) 0.033(2) 0.053(2) 0.0000(18) -0.017(2) 0.0068(18) C18 0.056(2) 0.037(2) 0.046(2) -0.0027(18) -0.0069(19) 0.0043(19) C19 0.046(2) 0.0317(19) 0.050(2) -0.0082(17) -0.0224(18) 0.0032(16) C20 0.054(2) 0.0315(19) 0.045(2) 0.0032(17) -0.0202(18) 0.0008(17) C21 0.049(2) 0.041(2) 0.041(2) -0.0074(18) -0.0128(17) 0.0036(18) C22 0.262(12) 0.054(4) 0.076(5) 0.014(3) -0.028(6) -0.082(6) C23 0.120(5) 0.064(4) 0.123(6) -0.013(4) -0.037(5) -0.046(4) C24 0.129(6) 0.076(4) 0.136(7) -0.031(4) -0.042(5) -0.045(4) C25 0.109(6) 0.081(5) 0.203(10) -0.045(5) -0.033(7) -0.038(4) C26 0.106(7) 0.069(5) 0.214(12) -0.010(6) -0.005(8) -0.031(4) C27 0.104(6) 0.063(4) 0.212(11) 0.037(6) -0.072(7) -0.037(4) C28 0.061(3) 0.079(3) 0.062(3) 0.003(3) -0.017(2) -0.032(3) C29 0.066(3) 0.091(4) 0.105(5) 0.026(4) -0.026(3) -0.040(3) C30 0.056(3) 0.182(8) 0.062(4) 0.022(5) -0.013(3) -0.051(4) C31 0.067(4) 0.199(9) 0.072(4) -0.024(6) -0.017(3) -0.048(5) C32 0.058(3) 0.114(5) 0.079(4) -0.027(4) -0.020(3) -0.028(3) C33 0.048(2) 0.074(3) 0.069(3) -0.006(3) -0.016(2) -0.021(2) O3 0.0613(18) 0.0370(15) 0.0589(18) 0.0013(14) -0.0138(15) 0.0120(14) O4 0.111(3) 0.056(2) 0.057(2) -0.0216(17) -0.0243(19) 0.035(2) O1 0.0510(15) 0.0340(14) 0.0552(16) -0.0011(13) -0.0101(13) 0.0029(12) O2 0.0611(18) 0.0471(17) 0.0485(16) -0.0065(14) -0.0082(14) 0.0101(14) O5 0.414(13) 0.130(5) 0.115(5) 0.027(4) -0.062(6) -0.162(7) O6 0.117(3) 0.071(2) 0.079(3) -0.015(2) -0.014(2) -0.038(2) O1W 0.313(10) 0.187(7) 0.175(6) 0.017(5) -0.122(7) -0.103(7) O2W 0.50(2) 0.205(10) 0.325(14) 0.044(10) -0.213(14) -0.076(13) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N2 2.007(3) . ? Cu1 N4 2.010(3) . ? Cu1 N3 2.019(4) . ? Cu1 N5 2.020(3) . ? Cu1 O3 2.360(3) 1_645 ? Cu1 O1 2.429(2) . ? N1 C5 1.426(6) . ? N1 C13 1.456(5) . ? N1 C4 1.480(5) . ? N2 C6 1.488(6) . ? N2 C5 1.489(5) . ? N2 H2 0.91 . ? N3 C7 1.478(5) . ? N3 C8 1.484(6) . ? N3 H3 0.91 . ? N4 C11 1.466(5) . ? N4 C10 1.468(5) . ? N4 H4 0.91 . ? N5 C12 1.483(5) . ? N5 C13 1.490(5) . ? N5 H5 0.91 . ? C1 C2 1.374(7) 2_666 ? C1 C3 1.385(5) . ? C1 H1 0.93 . ? C2 C1 1.374(7) 2_666 ? C2 C3 1.385(6) . ? C2 H2A 0.93 . ? C3 C4 1.502(6) . ? C4 H4A 0.97 . ? C4 H4B 0.97 . ? C5 H5A 0.97 . ? C5 H5B 0.97 . ? C6 C7 1.499(7) . ? C6 H6A 0.97 . ? C6 H6B 0.97 . ? C7 H7A 0.97 . ? C7 H7B 0.97 . ? C8 C9 1.524(7) . ? C8 H8A 0.97 . ? C8 H8B 0.97 . ? C9 C10 1.509(7) . ? C9 H9A 0.97 . ? C9 H9B 0.97 . ? C10 H10A 0.97 . ? C10 H10B 0.97 . ? C11 C12 1.500(6) . ? C11 H11A 0.97 . ? C11 H11B 0.97 . ? C12 H12A 0.97 . ? C12 H12B 0.97 . ? C13 H13A 0.97 . ? C13 H13B 0.97 . ? C15 O3 1.248(5) . ? C15 O4 1.267(5) . ? C15 C19 1.520(5) . ? C14 O1 1.237(4) . ? C14 O2 1.259(5) . ? C14 C16 1.515(5) . ? C16 C17 1.382(5) . ? C16 C21 1.384(5) . ? C17 C18 1.384(5) . ? C17 H17 0.93 . ? C18 C19 1.389(5) . ? C18 H18 0.93 . ? C19 C20 1.369(5) . ? C20 C21 1.387(5) . ? C20 H20 0.93 . ? C21 H21 0.93 . ? C22 O5 1.310(9) . ? C22 C23 1.409(12) . ? C22 C27 1.433(12) . ? C23 C24 1.292(9) . ? C23 H23 0.93 . ? C24 C25 1.379(11) . ? C24 H24 0.93 . ? C25 C26 1.356(13) . ? C25 H25 0.93 . ? C26 C27 1.313(13) . ? C26 H26 0.93 . ? C27 H27 0.93 . ? C28 O6 1.351(6) . ? C28 C33 1.375(7) . ? C28 C29 1.410(7) . ? C29 C30 1.409(9) . ? C29 H29 0.93 . ? C30 C31 1.331(11) . ? C30 H30 0.93 . ? C31 C32 1.373(9) . ? C31 H31 0.93 . ? C32 C33 1.372(7) . ? C32 H32 0.93 . ? C33 H33 0.93 . ? O3 Cu1 2.360(3) 1_465 ? O5 H5C 0.82 . ? O6 H6 0.82 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Cu1 N4 178.53(11) . . ? N2 Cu1 N3 86.16(14) . . ? N4 Cu1 N3 94.22(13) . . ? N2 Cu1 N5 93.58(13) . . ? N4 Cu1 N5 85.98(13) . . ? N3 Cu1 N5 177.69(11) . . ? N2 Cu1 O3 93.34(11) . 1_645 ? N4 Cu1 O3 88.05(11) . 1_645 ? N3 Cu1 O3 95.12(13) . 1_645 ? N5 Cu1 O3 87.19(12) . 1_645 ? N2 Cu1 O1 87.14(10) . . ? N4 Cu1 O1 91.47(10) . . ? N3 Cu1 O1 85.61(12) . . ? N5 Cu1 O1 92.09(11) . . ? O3 Cu1 O1 179.16(11) 1_645 . ? C5 N1 C13 115.2(3) . . ? C5 N1 C4 116.2(3) . . ? C13 N1 C4 117.0(3) . . ? C6 N2 C5 112.5(3) . . ? C6 N2 Cu1 106.5(3) . . ? C5 N2 Cu1 114.8(2) . . ? C6 N2 H2 107.6 . . ? C5 N2 H2 107.6 . . ? Cu1 N2 H2 107.6 . . ? C7 N3 C8 111.9(3) . . ? C7 N3 Cu1 106.6(3) . . ? C8 N3 Cu1 116.6(3) . . ? C7 N3 H3 107.1 . . ? C8 N3 H3 107.1 . . ? Cu1 N3 H3 107.1 . . ? C11 N4 C10 112.8(3) . . ? C11 N4 Cu1 106.8(2) . . ? C10 N4 Cu1 117.9(3) . . ? C11 N4 H4 106.2 . . ? C10 N4 H4 106.2 . . ? Cu1 N4 H4 106.2 . . ? C12 N5 C13 112.5(3) . . ? C12 N5 Cu1 106.9(2) . . ? C13 N5 Cu1 116.2(2) . . ? C12 N5 H5 106.9 . . ? C13 N5 H5 106.9 . . ? Cu1 N5 H5 106.9 . . ? C2 C1 C3 122.1(4) 2_666 . ? C2 C1 H1 118.9 2_666 . ? C3 C1 H1 118.9 . . ? C1 C2 C3 120.9(4) 2_666 . ? C1 C2 H2A 119.5 2_666 . ? C3 C2 H2A 119.5 . . ? C1 C3 C2 116.9(4) . . ? C1 C3 C4 124.4(4) . . ? C2 C3 C4 118.6(3) . . ? N1 C4 C3 112.9(3) . . ? N1 C4 H4A 109 . . ? C3 C4 H4A 109 . . ? N1 C4 H4B 109 . . ? C3 C4 H4B 109 . . ? H4A C4 H4B 107.8 . . ? N1 C5 N2 115.8(3) . . ? N1 C5 H5A 108.3 . . ? N2 C5 H5A 108.3 . . ? N1 C5 H5B 108.3 . . ? N2 C5 H5B 108.3 . . ? H5A C5 H5B 107.4 . . ? N2 C6 C7 108.4(3) . . ? N2 C6 H6A 110 . . ? C7 C6 H6A 110 . . ? N2 C6 H6B 110 . . ? C7 C6 H6B 110 . . ? H6A C6 H6B 108.4 . . ? N3 C7 C6 107.8(3) . . ? N3 C7 H7A 110.2 . . ? C6 C7 H7A 110.2 . . ? N3 C7 H7B 110.2 . . ? C6 C7 H7B 110.2 . . ? H7A C7 H7B 108.5 . . ? N3 C8 C9 111.7(4) . . ? N3 C8 H8A 109.3 . . ? C9 C8 H8A 109.3 . . ? N3 C8 H8B 109.3 . . ? C9 C8 H8B 109.3 . . ? H8A C8 H8B 107.9 . . ? C10 C9 C8 115.7(4) . . ? C10 C9 H9A 108.4 . . ? C8 C9 H9A 108.4 . . ? C10 C9 H9B 108.4 . . ? C8 C9 H9B 108.4 . . ? H9A C9 H9B 107.4 . . ? N4 C10 C9 113.2(3) . . ? N4 C10 H10A 108.9 . . ? C9 C10 H10A 108.9 . . ? N4 C10 H10B 108.9 . . ? C9 C10 H10B 108.9 . . ? H10A C10 H10B 107.7 . . ? N4 C11 C12 109.0(3) . . ? N4 C11 H11A 109.9 . . ? C12 C11 H11A 109.9 . . ? N4 C11 H11B 109.9 . . ? C12 C11 H11B 109.9 . . ? H11A C11 H11B 108.3 . . ? N5 C12 C11 108.1(3) . . ? N5 C12 H12A 110.1 . . ? C11 C12 H12A 110.1 . . ? N5 C12 H12B 110.1 . . ? C11 C12 H12B 110.1 . . ? H12A C12 H12B 108.4 . . ? N1 C13 N5 113.8(3) . . ? N1 C13 H13A 108.8 . . ? N5 C13 H13A 108.8 . . ? N1 C13 H13B 108.8 . . ? N5 C13 H13B 108.8 . . ? H13A C13 H13B 107.7 . . ? O3 C15 O4 124.6(3) . . ? O3 C15 C19 117.1(4) . . ? O4 C15 C19 118.1(3) . . ? O1 C14 O2 124.6(3) . . ? O1 C14 C16 117.7(3) . . ? O2 C14 C16 117.8(3) . . ? C17 C16 C21 117.9(3) . . ? C17 C16 C14 120.4(3) . . ? C21 C16 C14 121.7(3) . . ? C16 C17 C18 122.0(4) . . ? C16 C17 H17 119 . . ? C18 C17 H17 119 . . ? C17 C18 C19 119.1(4) . . ? C17 C18 H18 120.5 . . ? C19 C18 H18 120.5 . . ? C20 C19 C18 119.6(3) . . ? C20 C19 C15 119.4(3) . . ? C18 C19 C15 121.0(3) . . ? C19 C20 C21 120.6(3) . . ? C19 C20 H20 119.7 . . ? C21 C20 H20 119.7 . . ? C16 C21 C20 120.7(4) . . ? C16 C21 H21 119.6 . . ? C20 C21 H21 119.6 . . ? O5 C22 C23 117.7(11) . . ? O5 C22 C27 126.1(12) . . ? C23 C22 C27 116.1(8) . . ? C24 C23 C22 119.9(8) . . ? C24 C23 H23 120.1 . . ? C22 C23 H23 120.1 . . ? C23 C24 C25 124.9(9) . . ? C23 C24 H24 117.5 . . ? C25 C24 H24 117.5 . . ? C26 C25 C24 115.3(10) . . ? C26 C25 H25 122.4 . . ? C24 C25 H25 122.4 . . ? C27 C26 C25 124.2(10) . . ? C27 C26 H26 117.9 . . ? C25 C26 H26 117.9 . . ? C26 C27 C22 119.5(10) . . ? C26 C27 H27 120.2 . . ? C22 C27 H27 120.2 . . ? O6 C28 C33 123.3(4) . . ? O6 C28 C29 119.0(6) . . ? C33 C28 C29 117.7(6) . . ? C30 C29 C28 119.0(7) . . ? C30 C29 H29 120.5 . . ? C28 C29 H29 120.5 . . ? C31 C30 C29 121.8(7) . . ? C31 C30 H30 119.1 . . ? C29 C30 H30 119.1 . . ? C30 C31 C32 119.0(7) . . ? C30 C31 H31 120.5 . . ? C32 C31 H31 120.5 . . ? C33 C32 C31 121.3(7) . . ? C33 C32 H32 119.3 . . ? C31 C32 H32 119.3 . . ? C32 C33 C28 121.1(5) . . ? C32 C33 H33 119.5 . . ? C28 C33 H33 119.5 . . ? C15 O3 Cu1 130.4(3) . 1_465 ? C14 O1 Cu1 129.4(2) . . ? C22 O5 H5C 109.5 . . ? C28 O6 H6 109.5 . . ? #============================================================================= data_4 _database_code_depnum_ccdc_archive 'CCDC 747628' #TrackingRef 'CCDC 747628.cif' #============================================================================= _audit_creation_date 2011-12-12T09:40:21-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C27 H46 Cu N5 O12' _chemical_formula_sum 'C54 H92 Cu2 N10 O24' _chemical_formula_weight 1392.46 #----------------------------------------------------------------------------# # 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 16.5171(3) _cell_length_b 11.3860(3) _cell_length_c 17.9517(5) _cell_angle_alpha 90 _cell_angle_beta 106.9330(10) _cell_angle_gamma 90 _cell_volume 3229.70(14) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.432 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1472 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.744 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_av_R_equivalents 0.0691 _diffrn_reflns_av_unetI/netI 0.0898 _diffrn_reflns_number 13636 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.29 _diffrn_reflns_theta_max 27.41 _diffrn_reflns_theta_full 27.41 _diffrn_measured_fraction_theta_full 0.989 _diffrn_measured_fraction_theta_max 0.989 _reflns_number_total 7276 _reflns_number_gt 4094 _reflns_threshold_expression >2sigma(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, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # 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^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1318P)^2^+0.9559P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 7276 _refine_ls_number_parameters 409 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1473 _refine_ls_R_factor_gt 0.0878 _refine_ls_wR_factor_ref 0.2434 _refine_ls_wR_factor_gt 0.2482 _refine_ls_wR_factor_all 0.3174 _refine_ls_goodness_of_fit_gt 1.177 _refine_ls_goodness_of_fit_all 1.086 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.075 _refine_ls_restrained_S_gt 1.177 _refine_ls_shift/su_max -0.035 _refine_ls_shift/su_mean 0.006 _refine_diff_density_max 0.763 _refine_diff_density_min -1.034 _refine_diff_density_rms 0.233 #----------------------------------------------------------------------------# # 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 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' 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' O O 0.0106 0.006 '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 Cu Cu 0.27306(3) 0.25058(4) 0.19334(3) 0.0363(2) Uani 1 1 d . . . N1 N 0.3074(2) 0.0774(3) 0.0585(2) 0.0353(9) Uani 1 1 d . . . N2 N 0.2499(2) 0.0803(3) 0.1692(2) 0.0329(8) Uani 1 1 d . . . H2 H 0.295 0.0388 0.1986 0.039 Uiso 1 1 calc R . . N3 N 0.2079(2) 0.2304(3) 0.2711(2) 0.0379(9) Uani 1 1 d . . . H3 H 0.1571 0.2665 0.2509 0.046 Uiso 1 1 calc R . . N4 N 0.2988(3) 0.4214(3) 0.2198(2) 0.0460(10) Uani 1 1 d . . . H4 H 0.2496 0.4609 0.1982 0.055 Uiso 1 1 calc R . . N5 N 0.3412(2) 0.2718(3) 0.1184(2) 0.0352(9) Uani 1 1 d . . . H5 H 0.3955 0.2519 0.144 0.042 Uiso 1 1 calc R . . C1 C 0.4320(3) -0.0757(4) -0.0136(3) 0.0433(12) Uani 1 1 d . . . H1 H 0.386 -0.1265 -0.0229 0.052 Uiso 1 1 calc R . . C2 C 0.5137(3) 0.0820(4) 0.0585(3) 0.0413(11) Uani 1 1 d . . . H2A H 0.523 0.138 0.0978 0.05 Uiso 1 1 calc R . . C3 C 0.4462(3) 0.0076(4) 0.0466(3) 0.0356(11) Uani 1 1 d . . . C4 C 0.3859(3) 0.0136(4) 0.0966(3) 0.0423(12) Uani 1 1 d . . . H4A H 0.3719 -0.0656 0.1085 0.051 Uiso 1 1 calc R . . H4B H 0.4143 0.0521 0.1455 0.051 Uiso 1 1 calc R . . C5 C 0.2363(3) 0.0471(4) 0.0867(3) 0.0374(11) Uani 1 1 d . . . H5A H 0.2266 -0.0369 0.0811 0.045 Uiso 1 1 calc R . . H5B H 0.186 0.0864 0.0548 0.045 Uiso 1 1 calc R . . C6 C 0.1757(3) 0.0509(4) 0.1969(3) 0.0401(11) Uani 1 1 d . . . H6A H 0.1697 -0.0336 0.1995 0.048 Uiso 1 1 calc R . . H6B H 0.1243 0.0823 0.1613 0.048 Uiso 1 1 calc R . . C7 C 0.1903(3) 0.1047(4) 0.2773(3) 0.0466(12) Uani 1 1 d . . . H7A H 0.1404 0.0946 0.2948 0.056 Uiso 1 1 calc R . . H7B H 0.2378 0.0668 0.3144 0.056 Uiso 1 1 calc R . . C8 C 0.2470(4) 0.2830(5) 0.3489(3) 0.0543(14) Uani 1 1 d . . . H8A H 0.3012 0.246 0.3728 0.065 Uiso 1 1 calc R . . H8B H 0.2109 0.2686 0.382 0.065 Uiso 1 1 calc R . . C9 C 0.2596(4) 0.4149(5) 0.3428(3) 0.0621(16) Uani 1 1 d . . . H9A H 0.2057 0.4495 0.3145 0.075 Uiso 1 1 calc R . . H9B H 0.2755 0.4477 0.3949 0.075 Uiso 1 1 calc R . . C10 C 0.3244(4) 0.4517(5) 0.3037(3) 0.0599(15) Uani 1 1 d . . . H10A H 0.3331 0.5358 0.3095 0.072 Uiso 1 1 calc R . . H10B H 0.3778 0.4135 0.3292 0.072 Uiso 1 1 calc R . . C11 C 0.3591(3) 0.4635(4) 0.1792(4) 0.0605(16) Uani 1 1 d . . . H11A H 0.4167 0.4477 0.2105 0.073 Uiso 1 1 calc R . . H11B H 0.3529 0.5475 0.1706 0.073 Uiso 1 1 calc R . . C12 C 0.3406(3) 0.3993(4) 0.1014(3) 0.0504(14) Uani 1 1 d . . . H12A H 0.2858 0.4226 0.0674 0.06 Uiso 1 1 calc R . . H12B H 0.3834 0.4178 0.076 0.06 Uiso 1 1 calc R . . C13 C 0.3157(3) 0.2013(4) 0.0459(3) 0.0376(11) Uani 1 1 d . . . H13A H 0.262 0.2308 0.0131 0.045 Uiso 1 1 calc R . . H13B H 0.3574 0.2123 0.018 0.045 Uiso 1 1 calc R . . C14 C 0.4189(3) 0.0414(4) 0.3352(3) 0.0398(11) Uani 1 1 d . . . C15 C 0.4603(3) 0.0182(4) 0.4205(3) 0.0337(10) Uani 1 1 d . . . C16 C 0.5073(3) 0.1071(4) 0.4669(3) 0.0447(12) Uani 1 1 d . . . H16 H 0.5118 0.1799 0.4449 0.054 Uiso 1 1 calc R . . C17 C 0.4527(3) -0.0884(4) 0.4546(3) 0.0416(12) Uani 1 1 d . . . H17 H 0.4205 -0.1481 0.4248 0.05 Uiso 1 1 calc R . . C18 C 0.0299(3) 0.4486(4) 0.3515(3) 0.0359(11) Uani 1 1 d . . . C19 C 0.0167(3) 0.4735(3) 0.4301(3) 0.0332(10) Uani 1 1 d . . . C20 C 0.0402(3) 0.5807(4) 0.4668(3) 0.0356(11) Uani 1 1 d . . . H20 H 0.0673 0.6359 0.4442 0.043 Uiso 1 1 calc R . . C21 C -0.0241(3) 0.3933(4) 0.4638(3) 0.0365(11) Uani 1 1 d . . . H21 H -0.041 0.3214 0.4398 0.044 Uiso 1 1 calc R . . C22 C 0.1210(3) 0.6130(4) 0.1730(3) 0.0390(11) Uani 1 1 d . . . C23 C 0.1620(3) 0.6712(4) 0.2408(3) 0.0399(11) Uani 1 1 d . . . H23 H 0.144 0.6624 0.285 0.048 Uiso 1 1 calc R . . C24 C 0.2300(3) 0.7427(3) 0.2425(3) 0.0397(11) Uani 1 1 d . . . C25 C 0.2579(3) 0.7558(4) 0.1776(3) 0.0435(13) Uani 1 1 d . . . H25 H 0.3045 0.8029 0.1796 0.052 Uiso 1 1 calc R . . C26 C 0.2161(3) 0.6983(4) 0.1099(3) 0.0436(12) Uani 1 1 d . . . C27 C 0.1477(3) 0.6258(4) 0.1066(3) 0.0382(11) Uani 1 1 d . . . H27 H 0.1201 0.5865 0.0608 0.046 Uiso 1 1 calc R . . O1 O 0.1378(2) 0.3111(3) 0.1009(2) 0.0484(8) Uani 1 1 d . . . O2 O 0.4201(2) 0.1431(3) 0.3092(2) 0.0574(10) Uani 1 1 d . . . O3 O 0.3840(2) -0.0457(3) 0.29325(19) 0.0458(8) Uani 1 1 d . . . O4 O 0.0412(3) 0.3437(3) 0.3356(2) 0.0553(10) Uani 1 1 d . . . O5 O 0.0299(2) 0.5340(3) 0.30771(19) 0.0452(8) Uani 1 1 d . . . O6 O 0.0543(2) 0.5391(3) 0.1686(2) 0.0548(10) Uani 1 1 d . . . H6 H 0.0423 0.541 0.2098 0.082 Uiso 1 1 calc R . . O7 O 0.2682(3) 0.7991(3) 0.3119(2) 0.0592(10) Uani 1 1 d . . . H7 H 0.3076 0.8393 0.3071 0.089 Uiso 1 1 calc R . . O8 O 0.2464(3) 0.7160(4) 0.0472(2) 0.0627(11) Uani 1 1 d . . . H8 H 0.2115 0.6926 0.0074 0.094 Uiso 1 1 calc R . . O1W O 0.0093(2) 0.2725(3) 0.1854(2) 0.0487(9) Uani 1 1 d . . . O2W O 0.5175(3) 0.2460(3) 0.2210(3) 0.0669(12) Uani 1 1 d . . . O3W O 0.1499(3) 0.8709(4) 0.4041(2) 0.0811(13) Uani 1 1 d . . . O4W O 0.1016(3) 0.1545(4) 0.4421(2) 0.0800(13) 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 Cu 0.0353(4) 0.0468(4) 0.0285(4) -0.0075(2) 0.0118(3) -0.0066(2) N1 0.034(2) 0.047(2) 0.028(2) 0.0020(17) 0.0129(18) 0.0087(16) N2 0.0248(19) 0.048(2) 0.024(2) 0.0044(16) 0.0043(16) 0.0013(15) N3 0.035(2) 0.056(2) 0.022(2) -0.0001(17) 0.0073(17) 0.0058(17) N4 0.038(2) 0.050(2) 0.048(3) -0.010(2) 0.010(2) 0.0033(18) N5 0.028(2) 0.044(2) 0.036(2) -0.0005(17) 0.0134(18) -0.0020(15) C1 0.043(3) 0.039(3) 0.048(3) 0.004(2) 0.012(3) 0.004(2) C2 0.044(3) 0.043(3) 0.042(3) -0.005(2) 0.021(2) 0.008(2) C3 0.044(3) 0.038(2) 0.029(3) 0.009(2) 0.017(2) 0.016(2) C4 0.046(3) 0.050(3) 0.034(3) 0.011(2) 0.018(2) 0.010(2) C5 0.035(3) 0.047(3) 0.031(3) -0.008(2) 0.011(2) 0.0000(19) C6 0.036(3) 0.044(3) 0.044(3) 0.003(2) 0.016(2) -0.0035(19) C7 0.047(3) 0.062(3) 0.034(3) 0.010(2) 0.018(3) 0.002(2) C8 0.062(4) 0.077(4) 0.023(3) -0.006(3) 0.009(3) 0.019(3) C9 0.078(4) 0.073(4) 0.030(3) -0.018(3) 0.006(3) 0.021(3) C10 0.065(4) 0.056(3) 0.046(4) -0.020(3) -0.004(3) 0.002(3) C11 0.047(3) 0.047(3) 0.092(5) -0.008(3) 0.029(3) -0.006(2) C12 0.049(3) 0.043(3) 0.068(4) 0.010(3) 0.031(3) 0.003(2) C13 0.036(3) 0.052(3) 0.026(3) 0.008(2) 0.010(2) 0.009(2) C14 0.032(3) 0.051(3) 0.035(3) 0.000(2) 0.007(2) -0.001(2) C15 0.026(2) 0.045(3) 0.029(3) -0.003(2) 0.005(2) 0.0031(18) C16 0.054(3) 0.037(3) 0.038(3) 0.000(2) 0.006(3) -0.006(2) C17 0.044(3) 0.043(3) 0.031(3) -0.007(2) 0.001(2) -0.005(2) C18 0.032(3) 0.040(3) 0.035(3) -0.002(2) 0.010(2) -0.0019(18) C19 0.035(3) 0.035(2) 0.024(2) 0.0002(19) 0.001(2) 0.0058(17) C20 0.039(3) 0.032(2) 0.032(3) 0.0096(19) 0.005(2) -0.0044(18) C21 0.046(3) 0.034(2) 0.030(3) -0.0005(19) 0.011(2) -0.0072(19) C22 0.048(3) 0.033(2) 0.041(3) 0.000(2) 0.020(2) 0.001(2) C23 0.049(3) 0.040(2) 0.037(3) 0.000(2) 0.022(2) -0.001(2) C24 0.048(3) 0.037(2) 0.034(3) 0.001(2) 0.012(2) 0.001(2) C25 0.044(3) 0.043(3) 0.048(3) 0.006(2) 0.019(3) -0.002(2) C26 0.049(3) 0.046(3) 0.039(3) 0.005(2) 0.019(3) 0.009(2) C27 0.050(3) 0.035(2) 0.034(3) -0.001(2) 0.020(2) 0.001(2) O1 0.042(2) 0.060(2) 0.039(2) 0.0018(16) 0.0052(16) 0.0058(15) O2 0.070(3) 0.054(2) 0.043(2) 0.0066(17) 0.0090(19) -0.0101(17) O3 0.045(2) 0.054(2) 0.0324(19) -0.0030(16) 0.0016(16) -0.0065(15) O4 0.089(3) 0.044(2) 0.036(2) -0.0030(15) 0.022(2) 0.0036(17) O5 0.060(2) 0.0470(18) 0.034(2) 0.0063(15) 0.0227(17) 0.0012(15) O6 0.066(3) 0.059(2) 0.047(2) -0.0059(18) 0.029(2) -0.0223(18) O7 0.062(3) 0.070(2) 0.047(3) -0.0051(19) 0.017(2) -0.023(2) O8 0.068(3) 0.083(3) 0.048(3) 0.002(2) 0.034(2) -0.013(2) O1W 0.057(2) 0.0464(19) 0.047(2) -0.0046(15) 0.0211(19) -0.0070(15) O2W 0.054(3) 0.081(3) 0.060(3) -0.0013(19) 0.006(2) -0.0056(17) O3W 0.096(3) 0.099(3) 0.049(3) -0.002(2) 0.022(2) -0.015(3) O4W 0.099(4) 0.099(3) 0.046(3) -0.010(2) 0.028(3) -0.015(2) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 Cu N2 1.999(4) . ? Cu N5 2.005(4) . ? Cu N3 2.008(4) . ? Cu N4 2.018(4) . ? N1 C13 1.442(6) . ? N1 C5 1.449(5) . ? N1 C4 1.470(6) . ? N2 C5 1.482(5) . ? N2 C6 1.488(5) . ? N3 C7 1.471(6) . ? N3 C8 1.484(7) . ? N4 C11 1.476(6) . ? N4 C10 1.481(6) . ? N5 C12 1.482(6) . ? N5 C13 1.482(6) . ? C1 C2 1.372(6) 3_655 ? C1 C3 1.405(6) . ? C2 C3 1.366(6) . ? C2 C1 1.372(6) 3_655 ? C3 C4 1.524(6) . ? C6 C7 1.521(6) . ? C8 C9 1.524(8) . ? C9 C10 1.501(8) . ? C11 C12 1.526(7) . ? C14 O2 1.251(5) . ? C14 O3 1.277(5) . ? C14 C15 1.507(6) . ? C15 C17 1.382(6) . ? C15 C16 1.394(6) . ? C16 C17 1.388(6) 3_656 ? C17 C16 1.388(6) 3_656 ? C18 O5 1.251(5) . ? C18 O4 1.255(5) . ? C18 C19 1.515(6) . ? C19 C21 1.376(6) . ? C19 C20 1.387(6) . ? C20 C21 1.379(6) 3_566 ? C21 C20 1.379(6) 3_566 ? C22 O6 1.369(5) . ? C22 C23 1.378(6) . ? C22 C27 1.395(6) . ? C23 C24 1.382(6) . ? C24 C25 1.379(6) . ? C24 O7 1.380(6) . ? C25 C26 1.376(7) . ? C26 O8 1.375(6) . ? C26 C27 1.386(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Cu N5 94.68(13) . . ? N2 Cu N3 86.08(14) . . ? N5 Cu N3 178.28(15) . . ? N2 Cu N4 178.66(16) . . ? N5 Cu N4 85.48(15) . . ? N3 Cu N4 93.73(15) . . ? C13 N1 C5 114.3(3) . . ? C13 N1 C4 116.4(4) . . ? C5 N1 C4 114.5(3) . . ? C5 N2 C6 112.2(3) . . ? C5 N2 Cu 115.3(3) . . ? C6 N2 Cu 105.7(3) . . ? C7 N3 C8 111.3(4) . . ? C7 N3 Cu 108.8(3) . . ? C8 N3 Cu 115.7(3) . . ? C11 N4 C10 113.1(4) . . ? C11 N4 Cu 108.8(3) . . ? C10 N4 Cu 116.3(3) . . ? C12 N5 C13 111.5(4) . . ? C12 N5 Cu 106.5(3) . . ? C13 N5 Cu 116.9(3) . . ? C2 C1 C3 119.7(4) 3_655 . ? C3 C2 C1 121.2(4) . 3_655 ? C2 C3 C1 119.0(4) . . ? C2 C3 C4 121.5(4) . . ? C1 C3 C4 119.5(4) . . ? N1 C4 C3 112.7(4) . . ? N1 C5 N2 112.8(4) . . ? N2 C6 C7 107.9(4) . . ? N3 C7 C6 107.4(4) . . ? N3 C8 C9 111.2(4) . . ? C10 C9 C8 116.1(4) . . ? N4 C10 C9 112.2(4) . . ? N4 C11 C12 108.2(4) . . ? N5 C12 C11 107.1(4) . . ? N1 C13 N5 114.1(4) . . ? O2 C14 O3 123.5(4) . . ? O2 C14 C15 119.3(4) . . ? O3 C14 C15 117.2(4) . . ? C17 C15 C16 118.7(4) . . ? C17 C15 C14 122.1(4) . . ? C16 C15 C14 119.3(4) . . ? C17 C16 C15 120.9(4) 3_656 . ? C15 C17 C16 120.4(4) . 3_656 ? O5 C18 O4 124.7(4) . . ? O5 C18 C19 117.8(4) . . ? O4 C18 C19 117.5(4) . . ? C21 C19 C20 118.6(4) . . ? C21 C19 C18 120.5(4) . . ? C20 C19 C18 120.7(4) . . ? C21 C20 C19 121.2(4) 3_566 . ? C19 C21 C20 120.2(4) . 3_566 ? O6 C22 C23 121.8(4) . . ? O6 C22 C27 117.6(4) . . ? C23 C22 C27 120.5(4) . . ? C22 C23 C24 119.4(4) . . ? C25 C24 O7 122.4(4) . . ? C25 C24 C23 121.0(5) . . ? O7 C24 C23 116.6(4) . . ? C26 C25 C24 119.2(4) . . ? O8 C26 C25 116.4(4) . . ? O8 C26 C27 122.6(5) . . ? C25 C26 C27 121.0(4) . . ? C26 C27 C22 118.8(4) . . ? #=============================================================================# # End of CIF #=============================================================================#