# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2006 data_global _journal_coden_Cambridge 440 _publ_requested_journal 'New Journal of Chemistry' loop_ _publ_author_name 'Parthasarathi Dastidar' 'Amitava Das' 'D. Krishna Kumar' _publ_contact_author_name 'Dr Parthasarathi Dastidar' _publ_contact_author_address ; Analytical Science Discipline Central Salt and Marine Chemicals Research Institute G B Marg Bhavnagar Gujarat 364002 INDIA ; _publ_contact_author_email PARTHOD123@REDIFFMAIL.COM _publ_section_title ; Role of hydrogen-bond-functionalized and conformationally flexible bidentate ligand and anions on the supramolecular structural diversity in MOFs of Cu(II) ; # Attachment '1_kb378im_FINAL.cif' data_kb378im _database_code_depnum_ccdc_archive 'CCDC 612481' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H24 Cl2 Cu N8 O12' _chemical_formula_weight 726.93 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting MONOCLINIC _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.7969(6) _cell_length_b 17.9832(13) _cell_length_c 17.5198(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.3640(10) _cell_angle_gamma 90.00 _cell_volume 2771.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description BLOCK _exptl_crystal_colour PURPLE _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.742 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1484 _exptl_absorpt_coefficient_mu 1.061 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.6525 _exptl_absorpt_correction_T_max 0.8079 _exptl_absorpt_process_details 'BRUKER SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART CCD AREA DETECTOR' _diffrn_measurement_method 'PHI-OMEGA SCAN' _diffrn_detector_area_resol_mean 0.3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16591 _diffrn_reflns_av_R_equivalents 0.0343 _diffrn_reflns_av_sigmaI/netI 0.0472 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 28.31 _reflns_number_total 6375 _reflns_number_gt 5033 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER AXS SMART 3' _computing_cell_refinement 'BRUKER AXS SMART 3' _computing_data_reduction 'BRUKER AXS SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'BRUKER SHELXLTL' _computing_publication_material 'MERCURY 1.4' _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^)+(0.0550P)^2^+1.1883P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6375 _refine_ls_number_parameters 419 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0575 _refine_ls_R_factor_gt 0.0406 _refine_ls_wR_factor_ref 0.1042 _refine_ls_wR_factor_gt 0.0970 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.45889(3) 0.686931(16) 0.768201(17) 0.01073(9) Uani 1 1 d . . . N1 N 0.3800(2) 0.71929(11) 0.87178(12) 0.0123(4) Uani 1 1 d . . . C2 C 0.3555(3) 0.67024(14) 0.92813(14) 0.0141(5) Uani 1 1 d . . . H2 H 0.3805 0.6205 0.9208 0.017 Uiso 1 1 calc R . . C3 C 0.2934(3) 0.69242(14) 0.99729(15) 0.0173(5) Uani 1 1 d . . . H3 H 0.2723 0.6575 1.0349 0.021 Uiso 1 1 calc R . . C4 C 0.2633(3) 0.76690(14) 1.00959(14) 0.0145(5) Uani 1 1 d . . . H4 H 0.2211 0.7824 1.0554 0.017 Uiso 1 1 calc R . . C5 C 0.2966(3) 0.81846(13) 0.95287(14) 0.0121(5) Uani 1 1 d . . . C6 C 0.3493(3) 0.79155(14) 0.88325(14) 0.0127(5) Uani 1 1 d . . . H6 H 0.3637 0.8248 0.8433 0.015 Uiso 1 1 calc R . . N7 N 0.2753(2) 0.89402(12) 0.96731(12) 0.0140(4) Uani 1 1 d . . . H7 H 0.2099 0.9060 1.0014 0.017 Uiso 1 1 calc R . . C8 C 0.3514(3) 0.95116(14) 0.93098(14) 0.0130(5) Uani 1 1 d . . . O9 O 0.4389(2) 0.94244(10) 0.87846(10) 0.0179(4) Uani 1 1 d . . . N10 N 0.3186(3) 1.01888(11) 0.96315(12) 0.0150(5) Uani 1 1 d . . . H10 H 0.2689 1.0181 1.0053 0.018 Uiso 1 1 calc R . . C11 C 0.3575(3) 1.08875(13) 0.93466(14) 0.0120(5) Uani 1 1 d . . . C12 C 0.3219(3) 1.15096(14) 0.97857(14) 0.0153(5) Uani 1 1 d . . . H12 H 0.2761 1.1452 1.0259 0.018 Uiso 1 1 calc R . . C13 C 0.3549(3) 1.22103(15) 0.95151(15) 0.0162(5) Uani 1 1 d . . . H13 H 0.3319 1.2629 0.9804 0.019 Uiso 1 1 calc R . . C14 C 0.4225(3) 1.22840(14) 0.88094(14) 0.0138(5) Uani 1 1 d . . . H14 H 0.4453 1.2757 0.8629 0.017 Uiso 1 1 calc R . . N15 N 0.4564(2) 1.16873(11) 0.83761(12) 0.0120(4) Uani 1 1 d . . . C16 C 0.4251(3) 1.10019(14) 0.86397(14) 0.0130(5) Uani 1 1 d . . . H16 H 0.4494 1.0592 0.8341 0.016 Uiso 1 1 calc R . . N17 N 0.2566(2) 0.71863(11) 0.72272(11) 0.0116(4) Uani 1 1 d . . . C18 C 0.1430(3) 0.66933(14) 0.71517(15) 0.0146(5) Uani 1 1 d . . . H18 H 0.1598 0.6202 0.7294 0.017 Uiso 1 1 calc R . . C19 C 0.0012(3) 0.68938(14) 0.68679(15) 0.0169(5) Uani 1 1 d . . . H19 H -0.0752 0.6540 0.6810 0.020 Uiso 1 1 calc R . . C20 C -0.0244(3) 0.76228(14) 0.66742(15) 0.0161(5) Uani 1 1 d . . . H20 H -0.1191 0.7768 0.6488 0.019 Uiso 1 1 calc R . . C21 C 0.0918(3) 0.81459(14) 0.67575(14) 0.0121(5) Uani 1 1 d . . . C22 C 0.2323(3) 0.79013(14) 0.70248(13) 0.0115(5) Uani 1 1 d . . . H22 H 0.3118 0.8240 0.7065 0.014 Uiso 1 1 calc R . . N23 N 0.0600(2) 0.88739(11) 0.65400(12) 0.0143(4) Uani 1 1 d . . . H23 H -0.0252 0.8949 0.6310 0.017 Uiso 1 1 calc R . . C24 C 0.1519(3) 0.94892(14) 0.66570(14) 0.0136(5) Uani 1 1 d . . . O25 O 0.2778(2) 0.94562(10) 0.69310(11) 0.0202(4) Uani 1 1 d . . . N26 N 0.0803(2) 1.01300(11) 0.64163(12) 0.0142(5) Uani 1 1 d . . . H26 H -0.0088 1.0083 0.6218 0.017 Uiso 1 1 calc R . . C27 C 0.1396(3) 1.08466(14) 0.64666(14) 0.0121(5) Uani 1 1 d . . . C28 C 0.0573(3) 1.14342(14) 0.61387(15) 0.0154(5) Uani 1 1 d . . . H28 H -0.0347 1.1343 0.5891 0.018 Uiso 1 1 calc R . . C29 C 0.1135(3) 1.21459(15) 0.61854(15) 0.0178(6) Uani 1 1 d . . . H29 H 0.0588 1.2541 0.5979 0.021 Uiso 1 1 calc R . . C30 C 0.2519(3) 1.22717(14) 0.65414(14) 0.0155(5) Uani 1 1 d . . . H30 H 0.2903 1.2753 0.6565 0.019 Uiso 1 1 calc R . . N31 N 0.3324(2) 1.17099(11) 0.68552(12) 0.0123(4) Uani 1 1 d . . . C32 C 0.2759(3) 1.10137(14) 0.68305(14) 0.0134(5) Uani 1 1 d . . . H32 H 0.3301 1.0632 0.7066 0.016 Uiso 1 1 calc R . . Cl33 Cl -0.31600(7) 0.94369(3) 0.55857(3) 0.01250(13) Uani 1 1 d . . . O34 O 0.4511(2) 0.48137(11) 0.91659(11) 0.0206(4) Uani 1 1 d . . . O35 O -0.1993(2) 0.99753(11) 0.54119(11) 0.0226(4) Uani 1 1 d . . . O36 O -0.3483(2) 0.89810(10) 0.49394(10) 0.0191(4) Uani 1 1 d . . . O37 O -0.2611(2) 0.89695(11) 0.62132(10) 0.0190(4) Uani 1 1 d . . . Cl38 Cl 0.07802(7) 1.02616(4) 1.14857(4) 0.01889(15) Uani 1 1 d . . . O39 O -0.0690(3) 0.99958(13) 1.16692(13) 0.0372(6) Uani 1 1 d . . . O40 O 0.0722(3) 1.09758(13) 1.11376(14) 0.0385(6) Uani 1 1 d . . . O41 O 0.1547(3) 0.97405(14) 1.10017(14) 0.0523(8) Uani 1 1 d . . . O42 O 0.1648(3) 0.46833(13) 0.71907(13) 0.0341(5) Uani 1 1 d . . . O43 O 0.3919(2) 0.56103(10) 0.78196(11) 0.0172(4) Uani 1 1 d . . . H43B H 0.3265 0.5502 0.7503 0.026 Uiso 1 1 calc R . . O44 O 0.5659(2) 0.85344(11) 0.75656(12) 0.0192(4) Uani 1 1 d . . . H44A H 0.551(4) 0.888(2) 0.784(2) 0.046(12) Uiso 1 1 d . . . H44B H 0.618(5) 0.874(2) 0.722(2) 0.055(13) Uiso 1 1 d . . . H43A H 0.425(4) 0.5379(18) 0.820(2) 0.028(9) Uiso 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 0.01258(17) 0.01003(15) 0.00958(16) -0.00103(11) 0.00081(11) 0.00201(12) N1 0.0127(11) 0.0113(10) 0.0129(10) -0.0011(8) 0.0000(8) -0.0004(8) C2 0.0166(13) 0.0109(12) 0.0149(13) -0.0007(10) -0.0010(10) 0.0018(10) C3 0.0227(14) 0.0146(13) 0.0146(13) 0.0038(10) 0.0021(11) -0.0025(11) C4 0.0192(13) 0.0142(12) 0.0101(12) 0.0005(10) 0.0042(10) -0.0016(10) C5 0.0121(12) 0.0111(12) 0.0132(12) -0.0012(10) 0.0005(9) -0.0008(9) C6 0.0152(13) 0.0128(12) 0.0102(12) -0.0004(9) 0.0019(10) -0.0012(10) N7 0.0168(11) 0.0110(10) 0.0144(11) -0.0022(8) 0.0066(8) 0.0003(8) C8 0.0146(13) 0.0119(12) 0.0124(12) -0.0001(10) -0.0012(10) 0.0010(10) O9 0.0250(11) 0.0114(9) 0.0175(9) -0.0017(7) 0.0098(8) -0.0003(7) N10 0.0229(12) 0.0126(11) 0.0096(10) 0.0003(8) 0.0085(9) 0.0001(9) C11 0.0118(12) 0.0105(12) 0.0136(12) 0.0010(10) -0.0023(9) -0.0003(9) C12 0.0191(14) 0.0144(13) 0.0124(12) -0.0009(10) 0.0037(10) 0.0001(10) C13 0.0164(13) 0.0141(13) 0.0179(13) -0.0029(10) 0.0028(10) 0.0026(10) C14 0.0168(13) 0.0104(12) 0.0141(12) 0.0016(10) -0.0002(10) -0.0019(10) N15 0.0132(11) 0.0125(10) 0.0104(10) 0.0006(8) 0.0013(8) 0.0000(8) C16 0.0144(13) 0.0127(12) 0.0120(12) -0.0026(9) 0.0004(10) -0.0008(10) N17 0.0136(11) 0.0127(11) 0.0086(10) -0.0017(8) 0.0016(8) 0.0015(8) C18 0.0182(14) 0.0091(12) 0.0163(13) 0.0010(9) 0.0010(10) -0.0003(10) C19 0.0140(13) 0.0143(13) 0.0222(14) 0.0022(11) -0.0008(11) -0.0053(10) C20 0.0132(13) 0.0147(13) 0.0204(13) 0.0008(11) -0.0004(10) -0.0003(10) C21 0.0131(12) 0.0126(12) 0.0107(12) -0.0008(9) 0.0022(9) 0.0001(10) C22 0.0124(13) 0.0119(12) 0.0103(12) -0.0020(9) 0.0014(9) -0.0004(9) N23 0.0110(11) 0.0112(10) 0.0208(11) 0.0013(9) -0.0047(9) 0.0006(8) C24 0.0154(13) 0.0126(12) 0.0127(12) -0.0022(10) 0.0028(10) 0.0009(10) O25 0.0135(10) 0.0137(9) 0.0332(11) 0.0008(8) -0.0059(8) -0.0006(7) N26 0.0134(11) 0.0104(11) 0.0187(11) 0.0009(8) -0.0029(9) -0.0023(8) C27 0.0149(13) 0.0106(12) 0.0110(12) -0.0007(9) 0.0013(9) -0.0021(9) C28 0.0132(13) 0.0152(13) 0.0177(13) 0.0016(10) -0.0009(10) 0.0000(10) C29 0.0195(14) 0.0138(13) 0.0200(14) 0.0033(11) -0.0004(11) 0.0036(10) C30 0.0205(14) 0.0115(12) 0.0145(12) 0.0024(10) 0.0019(10) -0.0007(10) N31 0.0133(11) 0.0126(11) 0.0109(10) 0.0012(8) 0.0010(8) -0.0022(8) C32 0.0152(13) 0.0113(12) 0.0136(12) 0.0004(10) 0.0020(10) 0.0010(10) Cl33 0.0136(3) 0.0114(3) 0.0125(3) 0.0002(2) 0.0000(2) 0.0006(2) O34 0.0189(10) 0.0248(11) 0.0182(10) 0.0044(8) -0.0005(8) -0.0077(8) O35 0.0204(11) 0.0229(10) 0.0243(11) 0.0061(8) -0.0021(8) -0.0087(8) O36 0.0259(11) 0.0162(9) 0.0153(9) -0.0055(7) -0.0013(8) 0.0015(8) O37 0.0176(10) 0.0233(10) 0.0161(9) 0.0070(8) -0.0027(7) 0.0016(8) Cl38 0.0212(4) 0.0172(3) 0.0183(3) 0.0015(3) 0.0034(3) -0.0007(3) O39 0.0284(13) 0.0449(14) 0.0384(13) 0.0081(11) 0.0022(10) -0.0124(11) O40 0.0418(14) 0.0265(12) 0.0472(15) 0.0204(11) 0.0005(11) 0.0006(10) O41 0.087(2) 0.0323(14) 0.0384(15) -0.0066(11) 0.0355(14) -0.0009(13) O42 0.0307(13) 0.0357(13) 0.0358(13) 0.0022(10) -0.0093(10) -0.0027(10) O43 0.0218(11) 0.0151(10) 0.0147(10) 0.0033(8) -0.0027(8) -0.0018(8) O44 0.0220(11) 0.0158(10) 0.0197(10) -0.0018(9) 0.0047(8) 0.0025(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N31 2.023(2) 2_646 ? Cu1 N17 2.027(2) . ? Cu1 N15 2.029(2) 2_646 ? Cu1 N1 2.032(2) . ? Cu1 O43 2.3523(19) . ? N1 C2 1.342(3) . ? N1 C6 1.343(3) . ? C2 C3 1.391(4) . ? C2 H2 0.9300 . ? C3 C4 1.382(4) . ? C3 H3 0.9300 . ? C4 C5 1.392(3) . ? C4 H4 0.9300 . ? C5 C6 1.394(3) . ? C5 N7 1.395(3) . ? C6 H6 0.9300 . ? N7 C8 1.384(3) . ? N7 H7 0.8600 . ? C8 O9 1.214(3) 1 ? C8 O9 1.214(3) . ? C8 N10 1.373(3) . ? N10 C11 1.395(3) . ? N10 H10 0.8600 . ? C11 C16 1.393(3) . ? C11 C12 1.394(3) . ? C12 C13 1.378(4) . ? C12 H12 0.9300 . ? C13 C14 1.382(4) . ? C13 H13 0.9300 . ? C14 N15 1.349(3) . ? C14 H14 0.9300 . ? N15 C16 1.345(3) . ? N15 Cu1 2.029(2) 2_656 ? C16 H16 0.9300 . ? N17 C18 1.342(3) . ? N17 C22 1.351(3) . ? C18 C19 1.387(4) . ? C18 H18 0.9300 . ? C19 C20 1.373(4) . ? C19 H19 0.9300 . ? C20 C21 1.396(4) . ? C20 H20 0.9300 . ? C21 C22 1.390(3) . ? C21 N23 1.391(3) . ? C22 H22 0.9300 . ? N23 C24 1.385(3) . ? N23 H23 0.8600 . ? C24 O25 1.205(3) . ? C24 N26 1.378(3) . ? N26 C27 1.393(3) . ? N26 H26 0.8600 . ? C27 C32 1.387(4) . ? C27 C28 1.402(3) . ? C28 C29 1.375(4) . ? C28 H28 0.9300 . ? C29 C30 1.383(4) . ? C29 H29 0.9300 . ? C30 N31 1.349(3) . ? C30 H30 0.9300 . ? N31 C32 1.348(3) . ? N31 Cu1 2.023(2) 2_656 ? C32 H32 0.9300 . ? Cl33 O36 1.4250(18) . ? Cl33 O34 1.4380(19) 2_556 ? Cl33 O35 1.4451(19) . ? Cl33 O35 1.4451(19) 1 ? Cl33 O37 1.4635(18) . ? Cl33 O37 1.4635(18) 1 ? O34 Cl33 1.4380(19) 2_546 ? Cl38 O39 1.418(2) . ? Cl38 O40 1.423(2) 1 ? Cl38 O40 1.423(2) . ? Cl38 O41 1.435(2) . ? Cl38 O41 1.435(2) 1 ? Cl38 O42 1.451(2) 4_576 ? O42 Cl38 1.451(2) 4_575 ? O43 H43B 0.8200 . ? O43 H43A 0.83(3) . ? O44 H44A 0.80(4) . ? O44 H44B 0.85(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N31 Cu1 N17 171.81(8) 2_646 . ? N31 Cu1 N15 90.31(8) 2_646 2_646 ? N17 Cu1 N15 90.74(8) . 2_646 ? N31 Cu1 N1 89.83(8) 2_646 . ? N17 Cu1 N1 88.09(8) . . ? N15 Cu1 N1 172.58(8) 2_646 . ? N31 Cu1 O43 92.85(8) 2_646 . ? N17 Cu1 O43 95.23(8) . . ? N15 Cu1 O43 91.83(8) 2_646 . ? N1 Cu1 O43 95.57(8) . . ? C2 N1 C6 119.5(2) . . ? C2 N1 Cu1 121.73(17) . . ? C6 N1 Cu1 118.75(17) . . ? N1 C2 C3 121.2(2) . . ? N1 C2 H2 119.4 . . ? C3 C2 H2 119.4 . . ? C4 C3 C2 119.4(2) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C3 C4 C5 119.5(2) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? C4 C5 C6 117.8(2) . . ? C4 C5 N7 119.4(2) . . ? C6 C5 N7 122.8(2) . . ? N1 C6 C5 122.4(2) . . ? N1 C6 H6 118.8 . . ? C5 C6 H6 118.8 . . ? C8 N7 C5 125.0(2) . . ? C8 N7 H7 117.5 . . ? C5 N7 H7 117.5 . . ? O9 C8 N10 124.2(2) 1 . ? O9 C8 N10 124.2(2) . . ? O9 C8 N7 124.3(2) 1 . ? O9 C8 N7 124.3(2) . . ? N10 C8 N7 111.5(2) . . ? C8 N10 C11 126.8(2) . . ? C8 N10 H10 116.6 . . ? C11 N10 H10 116.6 . . ? C16 C11 C12 118.1(2) . . ? C16 C11 N10 123.9(2) . . ? C12 C11 N10 118.0(2) . . ? C13 C12 C11 119.7(2) . . ? C13 C12 H12 120.2 . . ? C11 C12 H12 120.2 . . ? C12 C13 C14 119.2(2) . . ? C12 C13 H13 120.4 . . ? C14 C13 H13 120.4 . . ? N15 C14 C13 121.7(2) . . ? N15 C14 H14 119.2 . . ? C13 C14 H14 119.2 . . ? C16 N15 C14 119.3(2) . . ? C16 N15 Cu1 122.57(17) . 2_656 ? C14 N15 Cu1 118.01(17) . 2_656 ? N15 C16 C11 122.0(2) . . ? N15 C16 H16 119.0 . . ? C11 C16 H16 119.0 . . ? C18 N17 C22 119.1(2) . . ? C18 N17 Cu1 120.29(17) . . ? C22 N17 Cu1 120.55(17) . . ? N17 C18 C19 122.1(2) . . ? N17 C18 H18 119.0 . . ? C19 C18 H18 119.0 . . ? C20 C19 C18 118.9(2) . . ? C20 C19 H19 120.6 . . ? C18 C19 H19 120.6 . . ? C19 C20 C21 119.9(2) . . ? C19 C20 H20 120.0 . . ? C21 C20 H20 120.0 . . ? C22 C21 N23 124.5(2) . . ? C22 C21 C20 118.1(2) . . ? N23 C21 C20 117.4(2) . . ? N17 C22 C21 121.9(2) . . ? N17 C22 H22 119.0 . . ? C21 C22 H22 119.0 . . ? C24 N23 C21 126.5(2) . . ? C24 N23 H23 116.7 . . ? C21 N23 H23 116.7 . . ? O25 C24 N26 125.4(2) . . ? O25 C24 N23 123.6(2) . . ? N26 C24 N23 111.0(2) . . ? C24 N26 C27 125.7(2) . . ? C24 N26 H26 117.1 . . ? C27 N26 H26 117.1 . . ? C32 C27 N26 123.5(2) . . ? C32 C27 C28 117.9(2) . . ? N26 C27 C28 118.6(2) . . ? C29 C28 C27 119.5(2) . . ? C29 C28 H28 120.2 . . ? C27 C28 H28 120.2 . . ? C28 C29 C30 119.6(2) . . ? C28 C29 H29 120.2 . . ? C30 C29 H29 120.2 . . ? N31 C30 C29 121.3(2) . . ? N31 C30 H30 119.4 . . ? C29 C30 H30 119.4 . . ? C32 N31 C30 119.4(2) . . ? C32 N31 Cu1 118.57(17) . 2_656 ? C30 N31 Cu1 122.00(17) . 2_656 ? N31 C32 C27 122.2(2) . . ? N31 C32 H32 118.9 . . ? C27 C32 H32 118.9 . . ? O36 Cl33 O34 110.53(12) . 2_556 ? O36 Cl33 O35 110.88(12) . . ? O34 Cl33 O35 109.74(12) 2_556 . ? O36 Cl33 O35 110.88(12) . 1 ? O34 Cl33 O35 109.74(12) 2_556 1 ? O36 Cl33 O37 109.25(11) . . ? O34 Cl33 O37 108.23(11) 2_556 . ? O35 Cl33 O37 108.15(11) . . ? O35 Cl33 O37 108.15(11) 1 . ? O36 Cl33 O37 109.25(11) . 1 ? O34 Cl33 O37 108.23(11) 2_556 1 ? O35 Cl33 O37 108.15(11) . 1 ? O35 Cl33 O37 108.15(11) 1 1 ? O39 Cl38 O40 111.78(14) . 1 ? O39 Cl38 O40 111.78(14) . . ? O39 Cl38 O41 110.28(16) . . ? O40 Cl38 O41 110.62(15) 1 . ? O40 Cl38 O41 110.62(15) . . ? O39 Cl38 O41 110.28(16) . 1 ? O40 Cl38 O41 110.62(15) 1 1 ? O40 Cl38 O41 110.62(15) . 1 ? O39 Cl38 O42 107.80(14) . 4_576 ? O40 Cl38 O42 108.71(14) 1 4_576 ? O40 Cl38 O42 108.71(14) . 4_576 ? O41 Cl38 O42 107.51(16) . 4_576 ? O41 Cl38 O42 107.51(16) 1 4_576 ? Cu1 O43 H43B 109.5 . . ? Cu1 O43 H43A 118(2) . . ? H43B O43 H43A 131.2 . . ? H44A O44 H44B 101(4) . . ? 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 N7 H7 O41 0.86 2.18 2.941(3) 147.9 1 N10 H10 O41 0.86 2.10 2.922(3) 158.7 1 N23 H23 O37 0.86 2.08 2.884(3) 155.1 1 N26 H26 O35 0.86 2.19 3.028(3) 163.8 1 O43 H43A O34 0.83(3) 1.99(4) 2.805(3) 167(3) 1 O43 H43B O42 0.82 2.12 2.821(3) 143.8 1 O44 H44A O9 0.80(4) 2.17(4) 2.898(3) 153(4) 1 O44 H44B O37 0.85(4) 2.11(4) 2.930(3) 165(4) 1_655 C2 H2 O34 0.93 2.58 3.505(3) 173.7 1 C6 H6 O44 0.93 2.40 3.139(3) 135.9 1 C12 H12 O40 0.93 2.52 3.380(3) 153.7 1 C13 H13 O36 0.93 2.48 3.325(3) 151.7 2_556 C14 H14 O44 0.93 2.52 3.297(3) 141.6 2_656 C20 H20 O37 0.93 2.54 3.291(3) 138.1 1 C22 H22 O44 0.93 2.45 3.282(3) 148.4 1 C30 H30 O44 0.93 2.42 3.184(3) 139.1 2_656 _diffrn_measured_fraction_theta_max 0.924 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.924 _refine_diff_density_max 0.866 _refine_diff_density_min -0.401 _refine_diff_density_rms 0.089 # Attachment '2_kb378bm_FINAL.cif' data_kb378bm _database_code_depnum_ccdc_archive 'CCDC 612482' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H24 Cu F6 N8 O10 S2' _chemical_formula_weight 826.17 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' _symmetry_cell_setting MONOCLINIC _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.0522(6) _cell_length_b 18.0988(12) _cell_length_c 19.5538(13) _cell_angle_alpha 90.00 _cell_angle_beta 95.2860(10) _cell_angle_gamma 90.00 _cell_volume 3190.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description BLOCK _exptl_crystal_colour PURPLE _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.720 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1676 _exptl_absorpt_coefficient_mu 0.919 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.6989 _exptl_absorpt_correction_T_max 0.8448 _exptl_absorpt_process_details 'BRUKER SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART CCD AREA DETECTOR' _diffrn_measurement_method 'PHI-OMEGA SCAN' _diffrn_detector_area_resol_mean 0.3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19144 _diffrn_reflns_av_R_equivalents 0.0374 _diffrn_reflns_av_sigmaI/netI 0.0527 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 28.31 _reflns_number_total 7415 _reflns_number_gt 5630 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER AXS SMART 3' _computing_cell_refinement 'BRUKER AXS SMART 3' _computing_data_reduction 'BRUKER AXS SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'BRUKER SHELXLTL' _computing_publication_material 'MERCURY 1.4' _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^)+(0.0560P)^2^+0.0579P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7415 _refine_ls_number_parameters 476 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0632 _refine_ls_R_factor_gt 0.0427 _refine_ls_wR_factor_ref 0.1053 _refine_ls_wR_factor_gt 0.0970 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _refine_ls_shift/su_max 0.018 _refine_ls_shift/su_mean 0.001 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 0.46713(3) 0.247874(16) 0.253786(15) 0.01358(9) Uani 1 1 d . . . N1 N 0.6671(2) 0.27009(11) 0.21971(10) 0.0146(4) Uani 1 1 d . . . C2 C 0.7456(3) 0.21343(14) 0.19768(13) 0.0178(5) Uani 1 1 d . . . H2 H 0.7096 0.1656 0.2012 0.021 Uiso 1 1 calc R . . C3 C 0.8789(3) 0.22459(15) 0.16984(14) 0.0204(6) Uani 1 1 d . . . H3 H 0.9324 0.1845 0.1555 0.025 Uiso 1 1 calc R . . C4 C 0.9318(3) 0.29541(14) 0.16358(13) 0.0180(5) Uani 1 1 d . . . H4 H 1.0209 0.3036 0.1446 0.022 Uiso 1 1 calc R . . C5 C 0.8504(3) 0.35470(13) 0.18596(12) 0.0134(5) Uani 1 1 d . . . C6 C 0.7184(3) 0.33951(13) 0.21454(12) 0.0145(5) Uani 1 1 d . . . H6 H 0.6641 0.3785 0.2305 0.017 Uiso 1 1 calc R . . N7 N 0.9081(2) 0.42554(11) 0.17861(10) 0.0136(4) Uani 1 1 d . . . H7 H 0.9963 0.4280 0.1657 0.016 Uiso 1 1 calc R . . C8 C 0.8399(3) 0.49166(13) 0.18965(12) 0.0118(5) Uani 1 1 d . . . O9 O 0.71493(18) 0.49748(9) 0.20729(9) 0.0154(4) Uani 1 1 d . . . N10 N 0.9317(2) 0.55078(11) 0.17867(10) 0.0138(4) Uani 1 1 d . . . H10 H 1.0213 0.5408 0.1705 0.017 Uiso 1 1 calc R . . C11 C 0.8915(3) 0.62488(13) 0.17978(12) 0.0124(5) Uani 1 1 d . . . C12 C 0.9720(3) 0.67625(14) 0.14527(13) 0.0187(6) Uani 1 1 d . . . H12 H 1.0530 0.6613 0.1227 0.022 Uiso 1 1 calc R . . C13 C 0.9302(3) 0.74937(14) 0.14494(14) 0.0223(6) Uani 1 1 d . . . H13 H 0.9850 0.7845 0.1235 0.027 Uiso 1 1 calc R . . C14 C 0.8059(3) 0.77042(14) 0.17672(13) 0.0200(6) Uani 1 1 d . . . H14 H 0.7747 0.8194 0.1740 0.024 Uiso 1 1 calc R . . N15 N 0.7300(2) 0.72160(11) 0.21130(10) 0.0137(4) Uani 1 1 d . . . C16 C 0.7741(3) 0.65069(13) 0.21478(12) 0.0124(5) Uani 1 1 d . . . H16 H 0.7249 0.6178 0.2413 0.015 Uiso 1 1 calc R . . N17 N 0.5490(2) 0.26799(11) 0.35238(11) 0.0160(5) Uani 1 1 d . . . C18 C 0.5733(3) 0.21384(15) 0.39879(15) 0.0288(7) Uani 1 1 d . . . H18 H 0.5541 0.1652 0.3856 0.035 Uiso 1 1 calc R . . C19 C 0.6264(4) 0.22890(16) 0.46588(16) 0.0380(8) Uani 1 1 d . . . H19 H 0.6430 0.1905 0.4972 0.046 Uiso 1 1 calc R . . C20 C 0.6545(3) 0.30050(15) 0.48631(14) 0.0260(6) Uani 1 1 d . . . H20 H 0.6911 0.3109 0.5313 0.031 Uiso 1 1 calc R . . C21 C 0.6275(3) 0.35721(13) 0.43876(12) 0.0144(5) Uani 1 1 d . . . C22 C 0.5759(3) 0.33821(13) 0.37175(12) 0.0141(5) Uani 1 1 d . . . H22 H 0.5595 0.3755 0.3393 0.017 Uiso 1 1 calc R . . N23 N 0.6505(2) 0.43002(11) 0.46082(10) 0.0138(4) Uani 1 1 d . . . H23 H 0.6784 0.4367 0.5036 0.017 Uiso 1 1 calc R . . C24 C 0.6327(3) 0.49219(13) 0.42026(13) 0.0137(5) Uani 1 1 d . . . O25 O 0.6015(2) 0.49180(9) 0.35869(9) 0.0181(4) Uani 1 1 d . . . N26 N 0.6539(2) 0.55600(11) 0.45891(10) 0.0137(4) Uani 1 1 d . . . H26 H 0.6644 0.5513 0.5029 0.016 Uiso 1 1 calc R . . C27 C 0.6597(3) 0.62740(13) 0.43229(12) 0.0136(5) Uani 1 1 d . . . C28 C 0.7282(3) 0.68164(14) 0.47504(13) 0.0217(6) Uani 1 1 d . . . H28 H 0.7680 0.6699 0.5193 0.026 Uiso 1 1 calc R . . C29 C 0.7357(3) 0.75278(15) 0.45060(14) 0.0260(6) Uani 1 1 d . . . H29 H 0.7795 0.7898 0.4785 0.031 Uiso 1 1 calc R . . C30 C 0.6782(3) 0.76873(14) 0.38460(13) 0.0195(6) Uani 1 1 d . . . H30 H 0.6859 0.8167 0.3682 0.023 Uiso 1 1 calc R . . N31 N 0.6112(2) 0.71717(11) 0.34324(10) 0.0138(4) Uani 1 1 d . . . C32 C 0.6010(3) 0.64770(13) 0.36689(12) 0.0145(5) Uani 1 1 d . . . H32 H 0.5531 0.6122 0.3385 0.017 Uiso 1 1 calc R . . F33 F 1.06411(17) 0.44898(9) 0.66117(8) 0.0265(4) Uani 1 1 d . . . F34 F 1.01706(19) 0.50909(10) 0.56670(8) 0.0332(4) Uani 1 1 d . . . F35 F 1.05281(17) 0.56790(9) 0.66226(8) 0.0275(4) Uani 1 1 d . . . C36 C 0.9936(3) 0.50730(14) 0.63274(13) 0.0186(6) Uani 1 1 d . . . S37 S 0.79428(7) 0.50261(3) 0.64175(3) 0.01317(14) Uani 1 1 d . . . O38 O 0.7846(2) 0.50446(10) 0.71491(9) 0.0196(4) Uani 1 1 d . . . O39 O 0.7374(2) 0.56815(9) 0.60565(9) 0.0186(4) Uani 1 1 d . . . O40 O 0.7506(2) 0.43401(9) 0.60809(9) 0.0194(4) Uani 1 1 d . . . F41 F 1.13726(19) 0.51719(11) -0.02870(9) 0.0395(5) Uani 1 1 d . . . F42 F 1.36626(18) 0.54851(9) -0.01097(8) 0.0270(4) Uani 1 1 d . . . F43 F 1.30820(19) 0.43481(9) -0.03159(8) 0.0315(4) Uani 1 1 d . . . C44 C 1.2690(3) 0.49591(15) -0.00037(14) 0.0203(6) Uani 1 1 d . . . S45 S 1.26185(7) 0.47994(3) 0.09147(3) 0.01356(14) Uani 1 1 d . . . O46 O 1.2151(2) 0.55019(10) 0.11691(9) 0.0202(4) Uani 1 1 d . . . O47 O 1.15173(19) 0.42218(10) 0.09408(9) 0.0193(4) Uani 1 1 d . . . O48 O 1.41090(19) 0.45853(10) 0.11576(9) 0.0192(4) Uani 1 1 d . . . O49 O 0.3935(2) 0.37748(10) 0.23726(10) 0.0177(4) Uani 1 1 d . . . O50 O 0.4576(3) 0.59715(11) 0.22179(11) 0.0208(4) Uani 1 1 d . . . H49A H 0.411(3) 0.3990(16) 0.2046(15) 0.017(8) Uiso 1 1 d . . . H49B H 0.348(4) 0.4072(19) 0.2571(17) 0.038(10) Uiso 1 1 d . . . H50A H 0.380(4) 0.584(2) 0.2112(19) 0.050(13) Uiso 1 1 d . . . H50B H 0.509(4) 0.5672(19) 0.2165(17) 0.039(11) Uiso 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 0.01466(16) 0.01230(16) 0.01416(16) -0.00338(12) 0.00346(11) -0.00431(12) N1 0.0159(11) 0.0137(11) 0.0140(11) -0.0026(8) 0.0014(8) -0.0025(8) C2 0.0196(14) 0.0126(13) 0.0213(14) -0.0019(10) 0.0025(11) -0.0014(10) C3 0.0196(14) 0.0132(13) 0.0291(15) -0.0052(11) 0.0051(11) 0.0023(10) C4 0.0152(13) 0.0154(13) 0.0241(14) -0.0045(10) 0.0060(11) -0.0001(10) C5 0.0165(13) 0.0108(12) 0.0130(13) 0.0001(9) 0.0017(10) -0.0009(9) C6 0.0149(13) 0.0120(12) 0.0168(13) -0.0018(10) 0.0022(10) -0.0005(9) N7 0.0109(10) 0.0107(10) 0.0199(11) -0.0009(8) 0.0057(8) 0.0004(8) C8 0.0120(12) 0.0124(12) 0.0108(12) -0.0009(9) 0.0009(9) 0.0006(9) O9 0.0102(9) 0.0130(9) 0.0239(10) -0.0006(7) 0.0056(7) 0.0007(7) N10 0.0107(10) 0.0101(10) 0.0214(11) -0.0003(8) 0.0051(8) -0.0002(8) C11 0.0132(12) 0.0110(12) 0.0125(12) -0.0017(9) -0.0011(9) 0.0011(9) C12 0.0184(13) 0.0195(14) 0.0193(14) 0.0008(10) 0.0081(11) 0.0013(10) C13 0.0247(15) 0.0174(13) 0.0263(15) 0.0058(11) 0.0109(12) -0.0020(11) C14 0.0254(15) 0.0126(13) 0.0226(14) 0.0020(10) 0.0051(11) 0.0034(11) N15 0.0151(11) 0.0121(10) 0.0137(11) 0.0011(8) 0.0006(8) 0.0015(8) C16 0.0145(12) 0.0115(12) 0.0109(12) 0.0001(9) 0.0007(9) -0.0002(9) N17 0.0168(11) 0.0136(11) 0.0179(11) -0.0025(8) 0.0028(9) -0.0011(8) C18 0.0458(19) 0.0102(14) 0.0287(16) -0.0011(11) -0.0057(14) -0.0032(12) C19 0.069(2) 0.0128(14) 0.0287(17) 0.0075(12) -0.0163(16) -0.0022(15) C20 0.0421(18) 0.0167(14) 0.0173(14) 0.0026(11) -0.0072(12) -0.0005(12) C21 0.0138(12) 0.0138(13) 0.0156(13) -0.0006(10) 0.0015(10) -0.0008(9) C22 0.0151(13) 0.0125(12) 0.0151(13) 0.0004(9) 0.0032(10) -0.0002(9) N23 0.0203(11) 0.0112(10) 0.0095(10) -0.0003(8) -0.0010(8) -0.0014(8) C24 0.0136(12) 0.0130(12) 0.0145(13) -0.0009(9) 0.0019(10) -0.0024(9) O25 0.0290(11) 0.0135(9) 0.0114(9) -0.0002(7) -0.0006(8) -0.0023(7) N26 0.0236(12) 0.0097(10) 0.0078(10) 0.0003(8) 0.0010(8) 0.0001(8) C27 0.0161(13) 0.0105(12) 0.0145(13) 0.0016(9) 0.0034(10) 0.0016(9) C28 0.0314(16) 0.0164(13) 0.0161(14) 0.0015(10) -0.0039(11) -0.0043(11) C29 0.0359(17) 0.0158(14) 0.0250(16) 0.0003(11) -0.0049(12) -0.0079(12) C30 0.0236(15) 0.0140(13) 0.0203(14) 0.0052(10) 0.0001(11) -0.0021(10) N31 0.0146(11) 0.0108(10) 0.0164(11) 0.0018(8) 0.0041(8) 0.0013(8) C32 0.0130(12) 0.0128(12) 0.0181(13) -0.0006(10) 0.0033(10) 0.0012(9) F33 0.0195(8) 0.0258(9) 0.0337(10) -0.0009(7) 0.0002(7) 0.0083(7) F34 0.0276(10) 0.0547(12) 0.0186(9) 0.0005(8) 0.0096(7) -0.0021(8) F35 0.0247(9) 0.0246(9) 0.0325(10) -0.0040(7) -0.0005(7) -0.0083(7) C36 0.0207(14) 0.0191(14) 0.0162(13) -0.0011(10) 0.0028(11) -0.0006(10) S37 0.0161(3) 0.0120(3) 0.0114(3) -0.0001(2) 0.0009(2) 0.0009(2) O38 0.0205(10) 0.0262(11) 0.0124(9) 0.0002(7) 0.0032(7) 0.0023(8) O39 0.0264(10) 0.0120(9) 0.0164(9) 0.0004(7) -0.0035(8) 0.0032(7) O40 0.0248(10) 0.0142(9) 0.0181(10) -0.0009(7) -0.0034(8) -0.0010(7) F41 0.0210(9) 0.0736(14) 0.0231(10) 0.0159(9) -0.0023(7) 0.0111(9) F42 0.0284(9) 0.0237(9) 0.0313(9) 0.0113(7) 0.0152(7) 0.0023(7) F43 0.0395(10) 0.0349(10) 0.0214(9) -0.0112(7) 0.0099(7) -0.0051(8) C44 0.0172(14) 0.0261(15) 0.0181(14) 0.0034(11) 0.0041(11) 0.0016(11) S45 0.0116(3) 0.0156(3) 0.0137(3) 0.0023(2) 0.0027(2) 0.0015(2) O46 0.0177(10) 0.0195(10) 0.0243(10) -0.0013(8) 0.0073(8) 0.0029(8) O47 0.0145(9) 0.0188(10) 0.0252(10) 0.0032(7) 0.0059(8) -0.0011(7) O48 0.0133(9) 0.0249(10) 0.0194(10) 0.0051(8) 0.0018(7) 0.0039(7) O49 0.0252(11) 0.0125(9) 0.0161(10) 0.0022(8) 0.0063(8) 0.0033(8) O50 0.0165(11) 0.0185(11) 0.0267(11) -0.0039(8) -0.0013(9) 0.0017(9) _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 N15 2.025(2) 2_645 ? Cu1 N1 2.026(2) . ? Cu1 N17 2.033(2) . ? Cu1 N31 2.040(2) 2_645 ? Cu1 O49 2.4518(19) . ? N1 C2 1.341(3) . ? N1 C6 1.346(3) . ? C2 C3 1.384(4) . ? C2 H2 0.9300 . ? C3 C4 1.378(4) . ? C3 H3 0.9300 . ? C4 C5 1.395(3) . ? C4 H4 0.9300 . ? C5 C6 1.392(3) . ? C5 N7 1.397(3) . ? C6 H6 0.9300 . ? N7 C8 1.373(3) . ? N7 H7 0.8600 . ? C8 O9 1.217(3) 1 ? C8 O9 1.217(3) . ? C8 N10 1.383(3) . ? N10 C11 1.390(3) . ? N10 H10 0.8600 . ? C11 C12 1.393(3) . ? C11 C16 1.396(3) . ? C12 C13 1.376(4) . ? C12 H12 0.9300 . ? C13 C14 1.388(4) . ? C13 H13 0.9300 . ? C14 N15 1.340(3) . ? C14 H14 0.9300 . ? N15 C16 1.344(3) . ? N15 Cu1 2.025(2) 2_655 ? C16 H16 0.9300 . ? N17 C18 1.340(3) . ? N17 C22 1.342(3) . ? C18 C19 1.382(4) . ? C18 H18 0.9300 . ? C19 C20 1.373(4) . ? C19 H19 0.9300 . ? C20 C21 1.391(3) . ? C20 H20 0.9300 . ? C21 C22 1.393(3) . ? C21 N23 1.396(3) . ? C22 H22 0.9300 . ? N23 C24 1.378(3) . ? N23 H23 0.8600 . ? C24 O25 1.211(3) . ? C24 N26 1.384(3) . ? N26 C27 1.396(3) . ? N26 H26 0.8600 . ? C27 C32 1.388(3) . ? C27 C28 1.397(3) . ? C28 C29 1.377(4) . ? C28 H28 0.9300 . ? C29 C30 1.377(4) . ? C29 H29 0.9300 . ? C30 N31 1.342(3) . ? C30 H30 0.9300 . ? N31 C32 1.346(3) . ? N31 Cu1 2.040(2) 2_655 ? C32 H32 0.9300 . ? F33 C36 1.328(3) . ? F34 C36 1.328(3) . ? F35 C36 1.329(3) . ? C36 S37 1.831(3) . ? S37 O38 1.4416(18) . ? S37 O40 1.4432(18) 1 ? S37 O40 1.4432(18) . ? S37 O39 1.4504(17) 1 ? S37 O39 1.4504(17) . ? F41 C44 1.325(3) . ? F42 C44 1.326(3) . ? F43 C44 1.327(3) . ? C44 S45 1.826(3) . ? S45 O48 1.4416(18) . ? S45 O46 1.4430(18) 1 ? S45 O46 1.4430(18) . ? S45 O47 1.4486(18) . ? S45 O47 1.4486(18) 1 ? O49 H49A 0.78(3) . ? O49 H49B 0.80(3) . ? O50 H50A 0.75(4) . ? O50 H50B 0.73(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N15 Cu1 N1 177.76(8) 2_645 . ? N15 Cu1 N17 88.73(8) 2_645 . ? N1 Cu1 N17 91.01(8) . . ? N15 Cu1 N31 90.46(8) 2_645 2_645 ? N1 Cu1 N31 89.58(8) . 2_645 ? N17 Cu1 N31 174.48(8) . 2_645 ? N15 Cu1 O49 91.82(8) 2_645 . ? N1 Cu1 O49 90.41(8) . . ? N17 Cu1 O49 91.41(8) . . ? N31 Cu1 O49 94.07(8) 2_645 . ? C2 N1 C6 119.5(2) . . ? C2 N1 Cu1 118.01(17) . . ? C6 N1 Cu1 122.32(17) . . ? N1 C2 C3 121.5(2) . . ? N1 C2 H2 119.3 . . ? C3 C2 H2 119.3 . . ? C4 C3 C2 119.6(2) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C3 C4 C5 119.3(2) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? C6 C5 C4 118.2(2) . . ? C6 C5 N7 124.4(2) . . ? C4 C5 N7 117.4(2) . . ? N1 C6 C5 121.9(2) . . ? N1 C6 H6 119.0 . . ? C5 C6 H6 119.0 . . ? C8 N7 C5 127.3(2) . . ? C8 N7 H7 116.4 . . ? C5 N7 H7 116.4 . . ? O9 C8 N7 124.3(2) 1 . ? O9 C8 N7 124.3(2) . . ? O9 C8 N10 124.3(2) 1 . ? O9 C8 N10 124.3(2) . . ? N7 C8 N10 111.4(2) . . ? C8 N10 C11 125.6(2) . . ? C8 N10 H10 117.2 . . ? C11 N10 H10 117.2 . . ? N10 C11 C12 119.1(2) . . ? N10 C11 C16 122.8(2) . . ? C12 C11 C16 118.0(2) . . ? C13 C12 C11 119.2(2) . . ? C13 C12 H12 120.4 . . ? C11 C12 H12 120.4 . . ? C12 C13 C14 119.7(2) . . ? C12 C13 H13 120.1 . . ? C14 C13 H13 120.1 . . ? N15 C14 C13 121.3(2) . . ? N15 C14 H14 119.3 . . ? C13 C14 H14 119.3 . . ? C14 N15 C16 119.4(2) . . ? C14 N15 Cu1 121.61(17) . 2_655 ? C16 N15 Cu1 118.31(16) . 2_655 ? N15 C16 C11 122.0(2) . . ? N15 C16 H16 119.0 . . ? C11 C16 H16 119.0 . . ? C18 N17 C22 119.2(2) . . ? C18 N17 Cu1 122.27(18) . . ? C22 N17 Cu1 118.55(17) . . ? N17 C18 C19 121.3(3) . . ? N17 C18 H18 119.3 . . ? C19 C18 H18 119.3 . . ? C20 C19 C18 120.1(3) . . ? C20 C19 H19 120.0 . . ? C18 C19 H19 120.0 . . ? C19 C20 C21 119.0(3) . . ? C19 C20 H20 120.5 . . ? C21 C20 H20 120.5 . . ? C20 C21 C22 118.0(2) . . ? C20 C21 N23 118.5(2) . . ? C22 C21 N23 123.4(2) . . ? N17 C22 C21 122.4(2) . . ? N17 C22 H22 118.8 . . ? C21 C22 H22 118.8 . . ? C24 N23 C21 125.9(2) . . ? C24 N23 H23 117.0 . . ? C21 N23 H23 117.0 . . ? O25 C24 N23 124.9(2) . . ? O25 C24 N26 123.8(2) . . ? N23 C24 N26 111.4(2) . . ? C24 N26 C27 125.2(2) . . ? C24 N26 H26 117.4 . . ? C27 N26 H26 117.4 . . ? C32 C27 N26 124.3(2) . . ? C32 C27 C28 118.5(2) . . ? N26 C27 C28 117.2(2) . . ? C29 C28 C27 118.9(2) . . ? C29 C28 H28 120.6 . . ? C27 C28 H28 120.6 . . ? C28 C29 C30 119.6(3) . . ? C28 C29 H29 120.2 . . ? C30 C29 H29 120.2 . . ? N31 C30 C29 122.0(2) . . ? N31 C30 H30 119.0 . . ? C29 C30 H30 119.0 . . ? C30 N31 C32 118.9(2) . . ? C30 N31 Cu1 118.03(17) . 2_655 ? C32 N31 Cu1 123.02(17) . 2_655 ? N31 C32 C27 122.1(2) . . ? N31 C32 H32 119.0 . . ? C27 C32 H32 119.0 . . ? F35 C36 F34 107.9(2) . . ? F35 C36 F33 108.4(2) . . ? F34 C36 F33 108.2(2) . . ? F35 C36 S37 110.96(17) . . ? F34 C36 S37 109.98(19) . . ? F33 C36 S37 111.24(17) . . ? O38 S37 O40 115.69(11) . 1 ? O38 S37 O40 115.69(11) . . ? O38 S37 O39 114.38(10) . 1 ? O40 S37 O39 114.30(11) 1 1 ? O40 S37 O39 114.30(11) . 1 ? O38 S37 O39 114.38(10) . . ? O40 S37 O39 114.30(11) 1 . ? O40 S37 O39 114.30(11) . . ? O38 S37 C36 104.17(12) . . ? O40 S37 C36 103.11(11) 1 . ? O40 S37 C36 103.11(11) . . ? O39 S37 C36 102.95(12) 1 . ? O39 S37 C36 102.95(12) . . ? F41 C44 F42 108.1(2) . . ? F41 C44 F43 108.5(2) . . ? F42 C44 F43 108.5(2) . . ? F41 C44 S45 110.18(18) . . ? F42 C44 S45 110.60(19) . . ? F43 C44 S45 110.84(18) . . ? O48 S45 O46 114.76(11) . 1 ? O48 S45 O46 114.76(11) . . ? O48 S45 O47 114.87(11) . . ? O46 S45 O47 113.51(11) 1 . ? O46 S45 O47 113.51(11) . . ? O48 S45 O47 114.87(11) . 1 ? O46 S45 O47 113.51(11) 1 1 ? O46 S45 O47 113.51(11) . 1 ? O48 S45 C44 104.45(11) . . ? O46 S45 C44 103.75(12) 1 . ? O46 S45 C44 103.75(12) . . ? O47 S45 C44 103.64(12) . . ? O47 S45 C44 103.64(12) 1 . ? Cu1 O49 H49A 121(2) . . ? Cu1 O49 H49B 137(2) . . ? H49A O49 H49B 103(3) . . ? H50A O50 H50B 109(4) . . ? 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 N7 H7 O47 0.86 2.08 2.876(3) 154.1 1 N10 H10 O46 0.86 2.13 2.934(3) 155.3 1 N23 H23 O40 0.86 2.09 2.939(3) 170.6 1 N26 H26 O39 0.86 2.08 2.907(3) 161.3 1 O49 H49A O48 0.78(3) 2.04(3) 2.809(3) 168(3) 1_455 O49 H49B O38 0.80(3) 2.10(3) 2.884(3) 166(3) 3_666 O50 H50A O46 0.75(4) 2.35(4) 2.987(3) 144(4) 1_455 O50 H50B O9 0.73(4) 2.27(4) 2.980(3) 165(4) 1 C2 H2 O50 0.93 2.55 3.290(3) 136.6 2_645 C12 H12 O46 0.93 2.50 3.252(3) 138.4 1 C14 H14 O39 0.93 2.44 3.270(3) 148.4 4_575 C16 H16 O50 0.93 2.44 3.039(3) 121.9 1 C18 H18 O50 0.93 2.43 3.159(4) 135.4 2_645 C28 H28 O39 0.93 2.53 3.272(3) 136.8 1 C30 H30 O47 0.93 2.48 3.184(3) 132.6 2_755 C32 H32 O50 0.93 2.38 3.145(3) 139.4 1 _diffrn_measured_fraction_theta_max 0.935 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.935 _refine_diff_density_max 0.640 _refine_diff_density_min -0.341 _refine_diff_density_rms 0.089 # Attachment '3_kkb4sifm_FINAL.cif' data_kkb4sifm _database_code_depnum_ccdc_archive 'CCDC 612483' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H24 Cu F6 N8 O5 Si' _chemical_formula_weight 698.13 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' O O 0.0106 0.0060 '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' Si Si 0.0817 0.0704 '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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting MONOCLINIC _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 21.398(2) _cell_length_b 17.9035(17) _cell_length_c 17.4386(17) _cell_angle_alpha 90.00 _cell_angle_beta 105.302(2) _cell_angle_gamma 90.00 _cell_volume 6443.9(11) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description PLATE _exptl_crystal_colour PURPLE _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.439 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2840 _exptl_absorpt_coefficient_mu 0.794 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.8322 _exptl_absorpt_correction_T_max 0.9319 _exptl_absorpt_process_details 'BRUKER SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART CCD AREA DETECTOR' _diffrn_measurement_method 'PHI-OMEGA SCAN' _diffrn_detector_area_resol_mean 0.3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19036 _diffrn_reflns_av_R_equivalents 0.0931 _diffrn_reflns_av_sigmaI/netI 0.1569 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.51 _diffrn_reflns_theta_max 28.36 _reflns_number_total 7419 _reflns_number_gt 3660 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER AXS SMART 3' _computing_cell_refinement 'BRUKER AXS SMART 3' _computing_data_reduction 'BRUKER AXS SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'BRUKER SHELXLTL' _computing_publication_material 'MERCURY 1.4' _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^)+(0.0871P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7419 _refine_ls_number_parameters 395 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1446 _refine_ls_R_factor_gt 0.0726 _refine_ls_wR_factor_ref 0.1931 _refine_ls_wR_factor_gt 0.1677 _refine_ls_goodness_of_fit_ref 0.921 _refine_ls_restrained_S_all 0.921 _refine_ls_shift/su_max 0.017 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.27627(3) 0.53219(4) 0.24238(4) 0.0224(2) Uani 1 1 d . . . N1 N 0.3617(2) 0.4964(3) 0.3135(2) 0.0244(10) Uani 1 1 d . . . C2 C 0.3662(2) 0.4291(3) 0.3461(3) 0.0223(12) Uani 1 1 d . . . H2 H 0.3289 0.4001 0.3381 0.027 Uiso 1 1 calc R . . C3 C 0.4248(3) 0.4000(3) 0.3922(3) 0.0322(15) Uani 1 1 d . . . C4 C 0.4797(3) 0.4451(3) 0.4058(4) 0.0474(19) Uani 1 1 d . . . H4 H 0.5191 0.4291 0.4385 0.057 Uiso 1 1 calc R . . C5 C 0.4741(3) 0.5140(4) 0.3695(4) 0.0470(18) Uani 1 1 d . . . H5 H 0.5104 0.5443 0.3761 0.056 Uiso 1 1 calc R . . C6 C 0.4156(3) 0.5381(3) 0.3240(3) 0.0310(14) Uani 1 1 d . . . H6 H 0.4129 0.5846 0.2996 0.037 Uiso 1 1 calc R . . N7 N 0.4296(2) 0.3292(3) 0.4266(3) 0.0364(13) Uani 1 1 d . . . H7 H 0.4561 0.3232 0.4728 0.044 Uiso 1 1 calc R . . C8 C 0.3945(3) 0.2684(3) 0.3910(3) 0.0287(13) Uani 1 1 d . . . O9 O 0.3495(2) 0.2725(2) 0.3337(3) 0.0514(13) Uani 1 1 d . . . N10 N 0.4174(2) 0.2024(3) 0.4293(3) 0.0426(15) Uani 1 1 d . . . H10 H 0.4476 0.2056 0.4729 0.051 Uiso 1 1 calc R . . C11 C 0.3952(3) 0.1302(3) 0.4029(3) 0.0250(13) Uani 1 1 d . . . C12 C 0.3328(2) 0.1174(3) 0.3543(3) 0.0258(13) Uani 1 1 d . . . H12 H 0.3052 0.1578 0.3379 0.031 Uiso 1 1 calc R . . N13 N 0.3117(2) 0.0490(2) 0.3309(2) 0.0227(10) Uani 1 1 d . . . C14 C 0.3512(3) -0.0090(3) 0.3549(3) 0.0299(14) Uani 1 1 d . . . H14 H 0.3366 -0.0567 0.3382 0.036 Uiso 1 1 calc R . . C15 C 0.4133(3) -0.0002(3) 0.4040(3) 0.0332(15) Uani 1 1 d . . . H15 H 0.4396 -0.0416 0.4204 0.040 Uiso 1 1 calc R . . C16 C 0.4355(3) 0.0700(3) 0.4281(3) 0.0301(14) Uani 1 1 d . . . H16 H 0.4770 0.0770 0.4610 0.036 Uiso 1 1 calc R . . N17 N 0.3065(2) 0.4967(2) 0.1476(2) 0.0204(10) Uani 1 1 d . . . C18 C 0.3084(3) 0.4239(3) 0.1327(3) 0.0254(13) Uani 1 1 d . . . H18 H 0.2967 0.3900 0.1668 0.030 Uiso 1 1 calc R . . C19 C 0.3276(2) 0.3969(3) 0.0670(3) 0.0219(12) Uani 1 1 d . . . C20 C 0.3466(3) 0.4480(3) 0.0177(3) 0.0250(13) Uani 1 1 d . . . H20 H 0.3608 0.4319 -0.0256 0.030 Uiso 1 1 calc R . . C21 C 0.3440(3) 0.5229(3) 0.0340(3) 0.0307(14) Uani 1 1 d . . . H21 H 0.3562 0.5581 0.0015 0.037 Uiso 1 1 calc R . . C22 C 0.3233(3) 0.5457(3) 0.0990(3) 0.0299(14) Uani 1 1 d . . . H22 H 0.3210 0.5965 0.1091 0.036 Uiso 1 1 calc R . . N23 N 0.3303(2) 0.3208(2) 0.0499(3) 0.0293(11) Uani 1 1 d . . . H23 H 0.3445 0.3099 0.0095 0.035 Uiso 1 1 calc R . . C24 C 0.3132(3) 0.2620(3) 0.0891(3) 0.0211(12) Uani 1 1 d . . . O25 O 0.2915(2) 0.2687(2) 0.1447(2) 0.0376(11) Uani 1 1 d . . . N26 N 0.3221(2) 0.1937(3) 0.0569(3) 0.0303(12) Uani 1 1 d . . . H26 H 0.3367 0.1943 0.0155 0.036 Uiso 1 1 calc R . . C27 C 0.3100(3) 0.1241(3) 0.0848(3) 0.0224(12) Uani 1 1 d . . . C28 C 0.2752(3) 0.1125(3) 0.1413(3) 0.0276(13) Uani 1 1 d . . . H28 H 0.2587 0.1536 0.1620 0.033 Uiso 1 1 calc R . . N29 N 0.2650(2) 0.0439(2) 0.1668(2) 0.0221(10) Uani 1 1 d . . . C30 C 0.2891(3) -0.0157(3) 0.1368(3) 0.0290(13) Uani 1 1 d . . . H30 H 0.2824 -0.0633 0.1545 0.035 Uiso 1 1 calc R . . C31 C 0.3235(3) -0.0077(3) 0.0804(3) 0.0291(13) Uani 1 1 d . . . H31 H 0.3397 -0.0498 0.0609 0.035 Uiso 1 1 calc R . . C32 C 0.3341(3) 0.0619(3) 0.0531(3) 0.0262(13) Uani 1 1 d . . . H32 H 0.3566 0.0675 0.0145 0.031 Uiso 1 1 calc R . . O33 O 0.30754(19) 0.6521(2) 0.2419(3) 0.0314(10) Uani 1 1 d . . . O34 O 0.22514(18) 0.3411(3) 0.2547(2) 0.0364(10) Uani 1 1 d . . . Si35 Si 0.57393(7) 0.23951(8) 0.59029(9) 0.0211(3) Uani 1 1 d . . . F36 F 0.51732(14) 0.17163(17) 0.57855(19) 0.0328(8) Uani 1 1 d . . . F37 F 0.63057(15) 0.30747(17) 0.59959(18) 0.0311(8) Uani 1 1 d . . . F38 F 0.62962(16) 0.17673(18) 0.5832(2) 0.0405(9) Uani 1 1 d . . . F39 F 0.55580(16) 0.2508(2) 0.48993(19) 0.0448(10) Uani 1 1 d . . . F40 F 0.59284(16) 0.2289(2) 0.68853(18) 0.0443(10) Uani 1 1 d . . . F41 F 0.51709(15) 0.30309(18) 0.5924(2) 0.0405(9) Uani 1 1 d . . . O42 O 0.3065(4) 0.7338(4) 0.0967(4) 0.108(2) Uiso 1 1 d . . . C43 C 0.2493(7) 0.7642(8) 0.0437(7) 0.135(5) Uiso 1 1 d . . . H33A H 0.335(3) 0.667(4) 0.291(4) 0.06(2) Uiso 1 1 d . . . H33B H 0.324(2) 0.665(2) 0.198(2) 0.12(4) Uiso 1 1 d . . . H34A H 0.1851 0.3351 0.2266 0.050 Uiso 1 1 d R . . H34B H 0.2522 0.3269 0.2437 0.050 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0196(4) 0.0258(4) 0.0188(3) -0.0032(3) -0.0005(2) 0.0060(3) N1 0.022(3) 0.031(3) 0.018(2) -0.009(2) -0.0007(19) 0.003(2) C2 0.018(3) 0.030(3) 0.017(3) -0.008(2) 0.001(2) 0.001(2) C3 0.030(3) 0.027(3) 0.031(3) -0.014(3) -0.007(3) 0.007(3) C4 0.027(4) 0.027(3) 0.072(5) -0.017(3) -0.016(3) 0.001(3) C5 0.025(4) 0.034(4) 0.073(5) -0.011(4) -0.005(3) -0.001(3) C6 0.025(3) 0.030(3) 0.035(3) -0.005(3) 0.002(2) 0.007(3) N7 0.036(3) 0.024(3) 0.033(3) -0.013(2) -0.020(2) 0.008(2) C8 0.026(3) 0.031(3) 0.025(3) -0.008(3) -0.001(2) 0.004(3) O9 0.048(3) 0.039(3) 0.043(3) 0.009(2) -0.030(2) -0.016(2) N10 0.029(3) 0.027(3) 0.052(3) -0.015(3) -0.025(2) 0.006(2) C11 0.019(3) 0.022(3) 0.030(3) -0.002(3) 0.001(2) -0.004(2) C12 0.018(3) 0.033(3) 0.023(3) -0.005(3) 0.001(2) 0.002(3) N13 0.020(2) 0.023(3) 0.020(2) 0.004(2) -0.0027(18) -0.004(2) C14 0.034(3) 0.024(3) 0.027(3) 0.007(3) -0.001(3) -0.001(3) C15 0.032(4) 0.026(3) 0.034(3) 0.010(3) -0.004(3) 0.001(3) C16 0.024(3) 0.028(3) 0.031(3) 0.001(3) -0.005(2) -0.002(3) N17 0.020(2) 0.019(2) 0.018(2) -0.0011(19) -0.0021(18) 0.0047(19) C18 0.034(3) 0.024(3) 0.017(3) 0.003(2) 0.003(2) -0.001(3) C19 0.017(3) 0.022(3) 0.024(3) -0.005(2) 0.001(2) 0.003(2) C20 0.028(3) 0.025(3) 0.019(3) 0.000(2) -0.001(2) 0.003(2) C21 0.044(4) 0.024(3) 0.027(3) 0.004(3) 0.015(3) 0.007(3) C22 0.043(4) 0.018(3) 0.026(3) 0.002(2) 0.005(3) 0.007(3) N23 0.050(3) 0.018(2) 0.024(2) -0.008(2) 0.017(2) -0.003(2) C24 0.021(3) 0.024(3) 0.015(3) -0.005(2) 0.001(2) 0.000(2) O25 0.063(3) 0.022(2) 0.038(2) -0.0027(19) 0.031(2) -0.001(2) N26 0.042(3) 0.024(3) 0.031(3) -0.002(2) 0.021(2) -0.007(2) C27 0.028(3) 0.021(3) 0.016(3) 0.005(2) 0.002(2) -0.004(2) C28 0.027(3) 0.030(3) 0.024(3) -0.007(3) 0.004(2) -0.008(3) N29 0.018(2) 0.023(3) 0.021(2) 0.007(2) -0.0005(18) -0.005(2) C30 0.024(3) 0.024(3) 0.037(3) 0.007(3) 0.006(3) -0.005(2) C31 0.028(3) 0.018(3) 0.042(4) 0.003(3) 0.010(3) 0.003(2) C32 0.029(3) 0.029(3) 0.020(3) -0.002(2) 0.004(2) 0.004(3) O33 0.022(2) 0.033(2) 0.035(2) -0.019(2) 0.0015(19) -0.0029(18) O34 0.018(2) 0.049(3) 0.041(2) -0.008(2) 0.0046(17) 0.003(2) Si35 0.0181(8) 0.0148(7) 0.0251(8) 0.0004(6) -0.0035(6) 0.0005(6) F36 0.0232(18) 0.0259(18) 0.046(2) -0.0048(16) 0.0029(15) -0.0072(15) F37 0.0321(19) 0.0197(17) 0.0404(19) -0.0068(15) 0.0076(15) -0.0089(14) F38 0.0300(19) 0.0206(18) 0.072(3) -0.0040(18) 0.0154(18) 0.0062(15) F39 0.0254(19) 0.078(3) 0.0276(19) 0.0002(18) 0.0018(15) -0.0069(18) F40 0.042(2) 0.060(3) 0.0227(18) 0.0032(17) -0.0051(15) -0.016(2) F41 0.032(2) 0.0224(18) 0.070(3) -0.0015(18) 0.0202(18) 0.0053(15) _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 N13 2.000(4) 4 ? Cu1 N29 2.019(4) 4 ? Cu1 N1 2.024(4) . ? Cu1 N17 2.029(4) . ? Cu1 O33 2.249(4) . ? N1 C2 1.325(7) . ? N1 C6 1.346(7) . ? C2 C3 1.399(7) . ? C2 H2 0.9300 . ? C3 C4 1.393(8) . ? C3 N7 1.396(8) . ? C4 C5 1.377(9) . ? C4 H4 0.9300 . ? C5 C6 1.362(8) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? N7 C8 1.374(7) . ? N7 H7 0.8600 . ? C8 O9 1.193(6) 1 ? C8 O9 1.193(6) . ? C8 N10 1.382(7) . ? N10 C11 1.411(7) . ? N10 H10 0.8600 . ? C11 C16 1.378(7) . ? C11 C12 1.399(7) . ? C12 N13 1.330(7) . ? C12 H12 0.9300 . ? N13 C14 1.333(7) . ? N13 Cu1 2.000(4) 4_545 ? C14 C15 1.387(7) . ? C14 H14 0.9300 . ? C15 C16 1.371(8) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? N17 C18 1.333(7) . ? N17 C22 1.333(7) . ? C18 C19 1.401(7) . ? C18 H18 0.9300 . ? C19 C20 1.389(7) . ? C19 N23 1.399(6) . ? C20 C21 1.376(8) . ? C20 H20 0.9300 . ? C21 C22 1.383(7) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? N23 C24 1.357(7) . ? N23 H23 0.8600 . ? C24 O25 1.186(6) 1 ? C24 O25 1.186(6) . ? C24 N26 1.380(7) . ? N26 C27 1.387(6) . ? N26 H26 0.8600 . ? C27 C28 1.399(7) . ? C27 C32 1.400(7) . ? C28 N29 1.342(7) . ? C28 H28 0.9300 . ? N29 C30 1.349(7) . ? N29 Cu1 2.019(4) 4_545 ? C30 C31 1.382(8) . ? C30 H30 0.9300 . ? C31 C32 1.374(7) . ? C31 H31 0.9300 . ? C32 H32 0.9300 . ? O33 H33A 0.93(7) . ? O33 H33B 0.96(4) . ? O34 H34A 0.8743 . ? O34 H34B 0.7034 . ? Si35 F40 1.664(3) . ? Si35 F38 1.667(3) . ? Si35 F41 1.673(3) 1 ? Si35 F41 1.673(3) . ? Si35 F36 1.690(3) 1 ? Si35 F36 1.690(3) . ? Si35 F37 1.695(3) . ? Si35 F39 1.702(4) . ? Si35 F39 1.702(4) 1 ? O42 C43 1.433(14) . ? C43 O42 1.433(14) 1 ? C43 C43 1.61(2) 7_565 ? 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 N13 Cu1 N29 87.27(17) 4 4 ? N13 Cu1 N1 170.19(19) 4 . ? N29 Cu1 N1 93.65(17) 4 . ? N13 Cu1 N17 88.63(17) 4 . ? N29 Cu1 N17 166.33(18) 4 . ? N1 Cu1 N17 88.22(17) . . ? N13 Cu1 O33 94.86(17) 4 . ? N29 Cu1 O33 95.51(17) 4 . ? N1 Cu1 O33 94.78(17) . . ? N17 Cu1 O33 97.82(17) . . ? C2 N1 C6 119.0(5) . . ? C2 N1 Cu1 120.2(4) . . ? C6 N1 Cu1 120.7(4) . . ? N1 C2 C3 122.5(5) . . ? N1 C2 H2 118.8 . . ? C3 C2 H2 118.8 . . ? C4 C3 N7 119.3(5) . . ? C4 C3 C2 118.0(6) . . ? N7 C3 C2 122.6(5) . . ? C5 C4 C3 118.2(6) . . ? C5 C4 H4 120.9 . . ? C3 C4 H4 120.9 . . ? C6 C5 C4 120.5(6) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? N1 C6 C5 121.7(6) . . ? N1 C6 H6 119.2 . . ? C5 C6 H6 119.2 . . ? C8 N7 C3 123.7(5) . . ? C8 N7 H7 118.1 . . ? C3 N7 H7 118.1 . . ? O9 C8 N7 123.7(6) 1 . ? O9 C8 N7 123.7(6) . . ? O9 C8 N10 124.2(6) 1 . ? O9 C8 N10 124.2(6) . . ? N7 C8 N10 112.1(5) . . ? C8 N10 C11 125.4(5) . . ? C8 N10 H10 117.3 . . ? C11 N10 H10 117.3 . . ? C16 C11 C12 118.8(5) . . ? C16 C11 N10 118.9(5) . . ? C12 C11 N10 122.2(5) . . ? N13 C12 C11 121.9(5) . . ? N13 C12 H12 119.0 . . ? C11 C12 H12 119.0 . . ? C12 N13 C14 119.0(5) . . ? C12 N13 Cu1 121.3(4) . 4_545 ? C14 N13 Cu1 119.6(4) . 4_545 ? N13 C14 C15 122.0(5) . . ? N13 C14 H14 119.0 . . ? C15 C14 H14 119.0 . . ? C16 C15 C14 119.4(5) . . ? C16 C15 H15 120.3 . . ? C14 C15 H15 120.3 . . ? C15 C16 C11 118.8(5) . . ? C15 C16 H16 120.6 . . ? C11 C16 H16 120.6 . . ? C18 N17 C22 119.5(5) . . ? C18 N17 Cu1 119.9(4) . . ? C22 N17 Cu1 120.6(4) . . ? N17 C18 C19 121.9(5) . . ? N17 C18 H18 119.0 . . ? C19 C18 H18 119.0 . . ? C20 C19 N23 118.3(5) . . ? C20 C19 C18 118.4(5) . . ? N23 C19 C18 123.3(5) . . ? C21 C20 C19 118.7(5) . . ? C21 C20 H20 120.7 . . ? C19 C20 H20 120.7 . . ? C20 C21 C22 119.8(5) . . ? C20 C21 H21 120.1 . . ? C22 C21 H21 120.1 . . ? N17 C22 C21 121.7(5) . . ? N17 C22 H22 119.2 . . ? C21 C22 H22 119.2 . . ? C24 N23 C19 128.0(5) . . ? C24 N23 H23 116.0 . . ? C19 N23 H23 116.0 . . ? O25 C24 N23 123.4(5) 1 . ? O25 C24 N23 123.4(5) . . ? O25 C24 N26 123.2(5) 1 . ? O25 C24 N26 123.2(5) . . ? N23 C24 N26 113.4(4) . . ? C24 N26 C27 126.5(4) . . ? C24 N26 H26 116.7 . . ? C27 N26 H26 116.7 . . ? N26 C27 C28 124.3(5) . . ? N26 C27 C32 117.0(5) . . ? C28 C27 C32 118.7(5) . . ? N29 C28 C27 122.1(5) . . ? N29 C28 H28 118.9 . . ? C27 C28 H28 118.9 . . ? C28 N29 C30 118.9(5) . . ? C28 N29 Cu1 119.8(4) . 4_545 ? C30 N29 Cu1 120.8(4) . 4_545 ? N29 C30 C31 121.5(5) . . ? N29 C30 H30 119.2 . . ? C31 C30 H30 119.2 . . ? C32 C31 C30 120.5(5) . . ? C32 C31 H31 119.7 . . ? C30 C31 H31 119.7 . . ? C31 C32 C27 118.2(5) . . ? C31 C32 H32 120.9 . . ? C27 C32 H32 120.9 . . ? Cu1 O33 H33A 113(4) . . ? Cu1 O33 H33B 114(3) . . ? H33A O33 H33B 113(5) . . ? H34A O34 H34B 123.9 . . ? F40 Si35 F38 90.88(19) . . ? F40 Si35 F41 92.0(2) . 1 ? F38 Si35 F41 177.1(2) . 1 ? F40 Si35 F41 92.0(2) . . ? F38 Si35 F41 177.1(2) . . ? F40 Si35 F36 90.82(18) . 1 ? F38 Si35 F36 90.56(17) . 1 ? F41 Si35 F36 89.43(17) 1 1 ? F41 Si35 F36 89.43(17) . 1 ? F40 Si35 F36 90.82(18) . . ? F38 Si35 F36 90.56(17) . . ? F41 Si35 F36 89.43(17) 1 . ? F41 Si35 F36 89.43(17) . . ? F40 Si35 F37 90.58(18) . . ? F38 Si35 F37 89.08(17) . . ? F41 Si35 F37 90.86(17) 1 . ? F41 Si35 F37 90.86(17) . . ? F36 Si35 F37 178.56(18) 1 . ? F36 Si35 F37 178.56(18) . . ? F40 Si35 F39 179.1(2) . . ? F38 Si35 F39 88.65(19) . . ? F41 Si35 F39 88.43(19) 1 . ? F41 Si35 F39 88.43(19) . . ? F36 Si35 F39 89.94(18) 1 . ? F36 Si35 F39 89.94(18) . . ? F37 Si35 F39 88.65(17) . . ? F40 Si35 F39 179.1(2) . 1 ? F38 Si35 F39 88.65(19) . 1 ? F41 Si35 F39 88.43(19) 1 1 ? F41 Si35 F39 88.43(19) . 1 ? F36 Si35 F39 89.94(18) 1 1 ? F36 Si35 F39 89.94(18) . 1 ? F37 Si35 F39 88.65(17) . 1 ? O42 C43 C43 105.3(13) 1 7_565 ? O42 C43 C43 105.3(13) . 7_565 ? 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 N7 H7 F39 0.86 2.45 2.984(6) 121.2 1 N7 H7 F41 0.86 2.18 3.037(6) 175.4 1 N10 H10 F36 0.86 2.13 2.952(5) 159.6 1 N10 H10 F39 0.86 2.40 2.998(6) 127.5 1 N23 H23 F37 0.86 2.11 2.950(5) 166.6 2_655 N23 H23 F39 0.86 2.38 2.981(6) 127.4 2_655 N26 H26 F38 0.86 2.06 2.908(6) 170.4 2_655 N26 H26 F39 0.86 2.54 3.108(6) 124.8 2_655 O33 H33A F37 0.93(7) 1.92(7) 2.827(5) 164(6) 5_666 O33 H33A F40 0.93(7) 2.39(7) 3.032(5) 126(5) 5_666 O33 H33B O42 0.96(4) 2.10(4) 2.919(9) 143(4) 1 O34 H34A F38 0.87 2.48 3.163(5) 135.5 8_455 O34 H34A F40 0.87 2.23 3.032(5) 153.1 8_455 O34 H34B O9 0.70 2.45 2.924(6) 126.2 1 O34 H34B O25 0.70 2.35 2.969(6) 147.0 1 C2 H2 O34 0.93 2.54 3.404(6) 154.5 1 C18 H18 O34 0.93 2.59 3.450(7) 154.4 1 C14 H14 F38 0.93 2.55 3.182(7) 125.6 5_656 C14 H14 O34 0.93 2.57 3.446(8) 158.0 4_545 C15 H15 F36 0.93 2.50 3.388(7) 159.5 5_656 C22 H22 O42 0.93 2.48 3.386(9) 164.7 1 C30 H30 O34 0.93 2.37 3.247(7) 158.2 4_545 _diffrn_measured_fraction_theta_max 0.919 _diffrn_reflns_theta_full 28.36 _diffrn_measured_fraction_theta_full 0.919 _refine_diff_density_max 0.922 _refine_diff_density_min -0.660 _refine_diff_density_rms 0.113 # Attachment '4_kkb450jm_FINAL.cif' data_kkb450jm _database_code_depnum_ccdc_archive 'CCDC 612484' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H24 Cu F6 N8 O4.50 Si' _chemical_formula_weight 678.12 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting MONOCLINIC _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 21.2107(14) _cell_length_b 17.9344(12) _cell_length_c 17.5455(12) _cell_angle_alpha 90.00 _cell_angle_beta 104.877(1) _cell_angle_gamma 90.00 _cell_volume 6450.6(7) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description PLATE _exptl_crystal_colour PURPLE _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.397 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2760 _exptl_absorpt_coefficient_mu 0.790 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.7861 _exptl_absorpt_correction_T_max 0.9395 _exptl_absorpt_process_details 'BRUKER SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART CCD AREA DETECTOR' _diffrn_measurement_method 'PHI-OMEGA SCAN' _diffrn_detector_area_resol_mean 0.3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12238 _diffrn_reflns_av_R_equivalents 0.0255 _diffrn_reflns_av_sigmaI/netI 0.0303 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 22.50 _reflns_number_total 4136 _reflns_number_gt 3686 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER AXS SMART 3' _computing_cell_refinement 'BRUKER AXS SMART 3' _computing_data_reduction 'BRUKER AXS SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'BRUKER SHELXLTL' _computing_publication_material 'MERCURY 1.4' _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^)+(0.0699P)^2^+13.3482P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4136 _refine_ls_number_parameters 389 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0442 _refine_ls_R_factor_gt 0.0403 _refine_ls_wR_factor_ref 0.1162 _refine_ls_wR_factor_gt 0.1124 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.223242(18) 0.03384(2) 0.75727(2) 0.01853(17) Uani 1 1 d . . . N1 N 0.26653(13) 0.04530(15) 0.66676(15) 0.0199(6) Uani 1 1 d . . . C2 C 0.27736(16) 0.11390(19) 0.64249(18) 0.0220(8) Uani 1 1 d . . . H2 H 0.2614 0.1548 0.6643 0.026 Uiso 1 1 calc R . . C3 C 0.31160(16) 0.12601(19) 0.58589(18) 0.0220(8) Uani 1 1 d . . . C4 C 0.33457(17) 0.06385(19) 0.5534(2) 0.0257(8) Uani 1 1 d . . . H4 H 0.3570 0.0697 0.5147 0.031 Uiso 1 1 calc R . . C5 C 0.32379(17) -0.0056(2) 0.5792(2) 0.0293(9) Uani 1 1 d . . . H5 H 0.3393 -0.0475 0.5584 0.035 Uiso 1 1 calc R . . C6 C 0.28981(17) -0.0136(2) 0.6361(2) 0.0279(8) Uani 1 1 d . . . H6 H 0.2830 -0.0611 0.6536 0.033 Uiso 1 1 calc R . . N7 N 0.32261(15) 0.19634(16) 0.55773(17) 0.0295(7) Uani 1 1 d . . . H7 H 0.3353 0.1976 0.5150 0.035 Uiso 1 1 calc R . . C8 C 0.31520(16) 0.26337(18) 0.5915(2) 0.0218(8) Uani 1 1 d . . . O9 O 0.29700(12) 0.27003(13) 0.65106(14) 0.0310(6) Uani 1 1 d . . . N10 N 0.33086(15) 0.32316(15) 0.55056(17) 0.0279(7) Uani 1 1 d . . . H10 H 0.3435 0.3128 0.5090 0.034 Uiso 1 1 calc R . . C11 C 0.32853(15) 0.39818(19) 0.56883(18) 0.0211(8) Uani 1 1 d . . . C12 C 0.30963(16) 0.42560(19) 0.63364(19) 0.0235(8) Uani 1 1 d . . . H12 H 0.2982 0.3920 0.6682 0.028 Uiso 1 1 calc R . . N13 N 0.30729(13) 0.49863(15) 0.64814(15) 0.0207(6) Uani 1 1 d . . . C14 C 0.32280(18) 0.5473(2) 0.5989(2) 0.0279(9) Uani 1 1 d . . . H14 H 0.3202 0.5981 0.6086 0.033 Uiso 1 1 calc R . . C15 C 0.34274(18) 0.5244(2) 0.5337(2) 0.0277(8) Uani 1 1 d . . . H15 H 0.3542 0.5594 0.5005 0.033 Uiso 1 1 calc R . . C16 C 0.34565(16) 0.44984(18) 0.51811(19) 0.0204(7) Uani 1 1 d . . . H16 H 0.3589 0.4338 0.4742 0.024 Uiso 1 1 calc R . . N17 N 0.31190(13) 0.05127(15) 0.83095(15) 0.0197(6) Uani 1 1 d . . . C18 C 0.33210(16) 0.11988(19) 0.85413(19) 0.0233(8) Uani 1 1 d . . . H18 H 0.3041 0.1599 0.8370 0.028 Uiso 1 1 calc R . . C19 C 0.39376(17) 0.13344(19) 0.90323(19) 0.0255(8) Uani 1 1 d . . . C20 C 0.43461(17) 0.0726(2) 0.9278(2) 0.0290(9) Uani 1 1 d . . . H20 H 0.4764 0.0796 0.9602 0.035 Uiso 1 1 calc R . . C21 C 0.41294(18) 0.0021(2) 0.9039(2) 0.0293(9) Uani 1 1 d . . . H21 H 0.4397 -0.0391 0.9203 0.035 Uiso 1 1 calc R . . C22 C 0.35094(17) -0.00691(19) 0.8551(2) 0.0257(8) Uani 1 1 d . . . H22 H 0.3362 -0.0546 0.8388 0.031 Uiso 1 1 calc R . . N23 N 0.41733(15) 0.20404(16) 0.92766(18) 0.0329(8) Uani 1 1 d . . . H23 H 0.4517 0.2061 0.9664 0.040 Uiso 1 1 calc R . . C24 C 0.39150(17) 0.2707(2) 0.8964(2) 0.0277(8) Uani 1 1 d . . . O25 O 0.34051(14) 0.27583(15) 0.84690(19) 0.0574(9) Uani 1 1 d . . . N26 N 0.42979(14) 0.33035(16) 0.92649(17) 0.0306(7) Uani 1 1 d . . . H26 H 0.4593 0.3240 0.9699 0.037 Uiso 1 1 calc R . . C27 C 0.42445(16) 0.40106(19) 0.89173(19) 0.0239(8) Uani 1 1 d . . . C28 C 0.36638(16) 0.43032(18) 0.84649(18) 0.0204(8) Uani 1 1 d . . . H28 H 0.3285 0.4020 0.8388 0.025 Uiso 1 1 calc R . . N29 N 0.36286(12) 0.49791(15) 0.81344(14) 0.0180(6) Uani 1 1 d . . . C30 C 0.41688(17) 0.53879(19) 0.8236(2) 0.0278(9) Uani 1 1 d . . . H30 H 0.4146 0.5850 0.7989 0.033 Uiso 1 1 calc R . . C31 C 0.47577(18) 0.5144(2) 0.8696(3) 0.0383(10) Uani 1 1 d . . . H31 H 0.5126 0.5445 0.8773 0.046 Uiso 1 1 calc R . . C32 C 0.47990(18) 0.4451(2) 0.9041(2) 0.0353(10) Uani 1 1 d . . . H32 H 0.5195 0.4280 0.9354 0.042 Uiso 1 1 calc R . . O33 O 0.19078(11) 0.15238(12) 0.75487(13) 0.0231(5) Uani 1 1 d . . . H33 H 0.1730 0.1645 0.7094 0.035 Uiso 1 1 calc R . . Si34 Si 0.42584(4) 0.23827(5) 0.41130(5) 0.0191(2) Uani 1 1 d . . . F35 F 0.36883(9) 0.30704(10) 0.40263(11) 0.0281(5) Uani 1 1 d . . . F36 F 0.36884(9) 0.17609(11) 0.42001(12) 0.0335(5) Uani 1 1 d . . . F37 F 0.44510(10) 0.25046(13) 0.51022(11) 0.0372(5) Uani 1 1 d . . . F38 F 0.48192(9) 0.17025(11) 0.42270(12) 0.0301(5) Uani 1 1 d . . . F39 F 0.48259(10) 0.30124(11) 0.40692(14) 0.0386(6) Uani 1 1 d . . . F40 F 0.40565(10) 0.22770(13) 0.31414(11) 0.0387(6) Uani 1 1 d . . . O41 O 0.22302(11) 0.34486(14) 0.75225(14) 0.0280(6) Uani 1 1 d . . . O42 O 0.5000 0.3221(2) 0.2500 0.0700(15) Uani 1 2 d S . . H33B H 0.1737(15) 0.1819(16) 0.7891(16) 0.080(18) Uiso 1 1 d . . . H41A H 0.2508 0.3177 0.7527 0.050 Uiso 1 1 d R . . H41B H 0.1884 0.3318 0.7282 0.050 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0202(3) 0.0174(3) 0.0158(3) 0.00080(16) 0.00076(18) -0.00373(16) N1 0.0200(15) 0.0199(16) 0.0171(14) 0.0025(12) 0.0001(12) -0.0037(12) C2 0.0248(18) 0.0190(19) 0.0210(17) -0.0043(15) 0.0036(14) -0.0021(15) C3 0.0222(18) 0.0212(19) 0.0201(17) -0.0030(15) 0.0007(14) -0.0039(15) C4 0.027(2) 0.024(2) 0.0270(19) 0.0012(16) 0.0082(15) -0.0003(16) C5 0.033(2) 0.020(2) 0.037(2) 0.0008(16) 0.0133(17) 0.0069(16) C6 0.0290(19) 0.021(2) 0.033(2) 0.0080(16) 0.0062(16) 0.0020(16) N7 0.049(2) 0.0199(17) 0.0254(16) -0.0005(13) 0.0201(14) -0.0052(14) C8 0.0206(18) 0.021(2) 0.0232(19) 0.0000(15) 0.0039(15) 0.0001(14) O9 0.0451(16) 0.0234(14) 0.0309(14) -0.0002(11) 0.0213(12) 0.0004(11) N10 0.0491(19) 0.0153(16) 0.0249(15) -0.0018(13) 0.0194(14) -0.0017(14) C11 0.0189(17) 0.024(2) 0.0182(17) -0.0026(15) -0.0003(14) -0.0009(14) C12 0.0276(19) 0.022(2) 0.0204(18) 0.0050(15) 0.0051(15) 0.0007(15) N13 0.0213(15) 0.0199(16) 0.0193(14) 0.0013(12) 0.0024(12) 0.0046(12) C14 0.037(2) 0.0203(19) 0.0254(19) 0.0039(16) 0.0065(17) 0.0057(16) C15 0.039(2) 0.024(2) 0.0219(19) 0.0063(15) 0.0102(16) -0.0002(16) C16 0.0220(18) 0.0229(19) 0.0151(16) 0.0002(14) 0.0024(14) 0.0023(14) N17 0.0229(15) 0.0175(15) 0.0166(14) 0.0035(12) 0.0010(12) -0.0014(12) C18 0.0247(19) 0.0196(19) 0.0220(18) 0.0038(15) -0.0003(15) -0.0013(15) C19 0.0280(19) 0.022(2) 0.0225(18) 0.0045(15) -0.0008(15) -0.0040(16) C20 0.0244(19) 0.026(2) 0.030(2) 0.0073(16) -0.0047(15) -0.0006(16) C21 0.031(2) 0.021(2) 0.030(2) 0.0069(16) -0.0021(16) 0.0024(16) C22 0.032(2) 0.0179(19) 0.0236(18) -0.0010(15) 0.0010(16) -0.0057(16) N23 0.0275(17) 0.0189(17) 0.0380(18) 0.0048(14) -0.0179(14) -0.0043(13) C24 0.026(2) 0.025(2) 0.0257(19) 0.0050(16) -0.0063(17) -0.0034(16) O25 0.0468(18) 0.0226(15) 0.074(2) 0.0114(15) -0.0377(17) -0.0068(13) N26 0.0285(17) 0.0213(17) 0.0300(16) 0.0065(14) -0.0143(13) -0.0035(13) C27 0.0251(19) 0.0187(19) 0.0237(18) -0.0010(15) -0.0013(15) -0.0002(15) C28 0.0207(18) 0.0204(19) 0.0187(17) -0.0046(14) 0.0024(14) -0.0026(14) N29 0.0198(15) 0.0166(15) 0.0156(14) -0.0013(12) 0.0012(11) 0.0016(12) C30 0.028(2) 0.0175(19) 0.037(2) 0.0038(15) 0.0063(17) 0.0003(16) C31 0.020(2) 0.025(2) 0.063(3) 0.008(2) -0.0016(19) -0.0036(16) C32 0.021(2) 0.023(2) 0.052(2) 0.0054(18) -0.0086(17) 0.0005(16) O33 0.0271(13) 0.0177(12) 0.0213(12) 0.0038(10) 0.0001(10) -0.0003(10) Si34 0.0181(5) 0.0163(5) 0.0203(5) 0.0016(4) 0.0002(4) -0.0010(4) F35 0.0304(11) 0.0227(11) 0.0308(11) 0.0018(8) 0.0069(9) 0.0065(9) F36 0.0280(11) 0.0229(11) 0.0484(13) -0.0001(10) 0.0073(10) -0.0072(9) F37 0.0257(11) 0.0589(15) 0.0235(11) -0.0058(10) -0.0001(9) 0.0033(10) F38 0.0267(11) 0.0233(11) 0.0367(11) 0.0044(9) 0.0016(9) 0.0061(9) F39 0.0329(12) 0.0212(11) 0.0654(15) 0.0048(10) 0.0193(11) -0.0049(9) F40 0.0343(12) 0.0573(15) 0.0220(11) 0.0000(10) 0.0026(9) 0.0157(11) O41 0.0228(13) 0.0275(15) 0.0312(14) -0.0044(11) 0.0025(11) 0.0005(11) O42 0.109(4) 0.040(3) 0.086(4) 0.000 0.071(3) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N17 2.014(3) . ? Cu1 N13 2.031(3) 4_546 ? Cu1 N29 2.031(3) 4_546 ? Cu1 N1 2.039(3) . ? Cu1 O33 2.232(2) . ? N1 C6 1.336(5) . ? N1 C2 1.341(4) . ? C2 C3 1.390(5) . ? C2 H2 0.9300 . ? C3 C4 1.396(5) . ? C3 N7 1.396(4) . ? C4 C5 1.364(5) . ? C4 H4 0.9300 . ? C5 C6 1.382(5) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? N7 C8 1.367(4) . ? N7 H7 0.8600 . ? C8 O9 1.209(4) 1 ? C8 O9 1.209(4) . ? C8 N10 1.378(4) . ? N10 C11 1.387(4) . ? N10 H10 0.8600 . ? C11 C12 1.389(5) . ? C11 C16 1.396(5) . ? C12 N13 1.338(5) . ? C12 H12 0.9300 . ? N13 C14 1.328(4) . ? N13 Cu1 2.031(3) 4_556 ? C14 C15 1.381(5) . ? C14 H14 0.9300 . ? C15 C16 1.369(5) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? N17 C18 1.332(4) . ? N17 C22 1.332(4) . ? C18 C19 1.390(5) . ? C18 H18 0.9300 . ? C19 N23 1.388(4) . ? C19 C20 1.391(5) . ? C20 C21 1.374(5) . ? C20 H20 0.9300 . ? C21 C22 1.382(5) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? N23 C24 1.370(5) . ? N23 H23 0.8600 . ? C24 O25 1.204(4) 1 ? C24 O25 1.204(4) . ? C24 N26 1.364(5) . ? N26 C27 1.399(4) . ? N26 H26 0.8600 . ? C27 C28 1.386(5) . ? C27 C32 1.387(5) . ? C28 N29 1.338(4) . ? C28 H28 0.9300 . ? N29 C30 1.333(4) . ? N29 Cu1 2.031(3) 4_556 ? C30 C31 1.373(5) . ? C30 H30 0.9300 . ? C31 C32 1.375(5) . ? C31 H31 0.9300 . ? C32 H32 0.9300 . ? O33 H33 0.8200 . ? O33 H33B 0.94(3) . ? Si34 F40 1.658(2) . ? Si34 F39 1.666(2) . ? Si34 F38 1.680(2) . ? Si34 F36 1.680(2) 1 ? Si34 F36 1.680(2) . ? Si34 F37 1.692(2) 1 ? Si34 F37 1.692(2) . ? Si34 F35 1.706(2) 1 ? Si34 F35 1.706(2) . ? O41 H41A 0.7640 . ? O41 H41B 0.7829 . ? 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 N17 Cu1 N13 87.98(10) . 4_546 ? N17 Cu1 N29 170.43(11) . 4_546 ? N13 Cu1 N29 88.58(10) 4_546 4_546 ? N17 Cu1 N1 87.21(11) . . ? N13 Cu1 N1 165.89(11) 4_546 . ? N29 Cu1 N1 94.03(10) 4_546 . ? N17 Cu1 O33 95.56(10) . . ? N13 Cu1 O33 98.63(10) 4_546 . ? N29 Cu1 O33 93.78(10) 4_546 . ? N1 Cu1 O33 95.04(10) . . ? C6 N1 C2 119.1(3) . . ? C6 N1 Cu1 121.4(2) . . ? C2 N1 Cu1 119.2(2) . . ? N1 C2 C3 122.3(3) . . ? N1 C2 H2 118.9 . . ? C3 C2 H2 118.9 . . ? C2 C3 C4 117.9(3) . . ? C2 C3 N7 124.0(3) . . ? C4 C3 N7 118.0(3) . . ? C5 C4 C3 119.2(3) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? C4 C5 C6 119.8(3) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? N1 C6 C5 121.6(3) . . ? N1 C6 H6 119.2 . . ? C5 C6 H6 119.2 . . ? C8 N7 C3 126.3(3) . . ? C8 N7 H7 116.8 . . ? C3 N7 H7 116.8 . . ? O9 C8 N7 124.0(3) 1 . ? O9 C8 N7 124.0(3) . . ? O9 C8 N10 123.1(3) 1 . ? O9 C8 N10 123.1(3) . . ? N7 C8 N10 112.8(3) . . ? C8 N10 C11 127.3(3) . . ? C8 N10 H10 116.3 . . ? C11 N10 H10 116.3 . . ? N10 C11 C12 124.6(3) . . ? N10 C11 C16 117.8(3) . . ? C12 C11 C16 117.6(3) . . ? N13 C12 C11 122.3(3) . . ? N13 C12 H12 118.8 . . ? C11 C12 H12 118.8 . . ? C14 N13 C12 119.5(3) . . ? C14 N13 Cu1 120.7(2) . 4_556 ? C12 N13 Cu1 119.7(2) . 4_556 ? N13 C14 C15 121.5(3) . . ? N13 C14 H14 119.3 . . ? C15 C14 H14 119.3 . . ? C16 C15 C14 119.8(3) . . ? C16 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? C15 C16 C11 119.2(3) . . ? C15 C16 H16 120.4 . . ? C11 C16 H16 120.4 . . ? C18 N17 C22 120.1(3) . . ? C18 N17 Cu1 120.9(2) . . ? C22 N17 Cu1 119.0(2) . . ? N17 C18 C19 121.9(3) . . ? N17 C18 H18 119.1 . . ? C19 C18 H18 119.1 . . ? N23 C19 C18 123.9(3) . . ? N23 C19 C20 118.3(3) . . ? C18 C19 C20 117.8(3) . . ? C21 C20 C19 119.6(3) . . ? C21 C20 H20 120.2 . . ? C19 C20 H20 120.2 . . ? C20 C21 C22 119.1(3) . . ? C20 C21 H21 120.4 . . ? C22 C21 H21 120.4 . . ? N17 C22 C21 121.4(3) . . ? N17 C22 H22 119.3 . . ? C21 C22 H22 119.3 . . ? C24 N23 C19 126.7(3) . . ? C24 N23 H23 116.7 . . ? C19 N23 H23 116.7 . . ? O25 C24 N26 123.7(3) 1 . ? O25 C24 N26 123.7(3) . . ? O25 C24 N23 123.2(3) 1 . ? O25 C24 N23 123.2(3) . . ? N26 C24 N23 113.1(3) . . ? C24 N26 C27 124.6(3) . . ? C24 N26 H26 117.7 . . ? C27 N26 H26 117.7 . . ? C28 C27 C32 117.8(3) . . ? C28 C27 N26 123.6(3) . . ? C32 C27 N26 118.5(3) . . ? N29 C28 C27 122.3(3) . . ? N29 C28 H28 118.9 . . ? C27 C28 H28 118.9 . . ? C30 N29 C28 119.3(3) . . ? C30 N29 Cu1 121.0(2) . 4_556 ? C28 N29 Cu1 119.6(2) . 4_556 ? N29 C30 C31 121.6(3) . . ? N29 C30 H30 119.2 . . ? C31 C30 H30 119.2 . . ? C30 C31 C32 119.5(3) . . ? C30 C31 H31 120.3 . . ? C32 C31 H31 120.3 . . ? C31 C32 C27 119.4(3) . . ? C31 C32 H32 120.3 . . ? C27 C32 H32 120.3 . . ? Cu1 O33 H33 109.5 . . ? Cu1 O33 H33B 133.8(18) . . ? H33 O33 H33B 108.5 . . ? F40 Si34 F39 91.66(12) . . ? F40 Si34 F38 91.58(11) . . ? F39 Si34 F38 89.99(11) . . ? F40 Si34 F36 90.90(12) . 1 ? F39 Si34 F36 177.34(12) . 1 ? F38 Si34 F36 90.64(10) . 1 ? F40 Si34 F36 90.90(12) . . ? F39 Si34 F36 177.34(12) . . ? F38 Si34 F36 90.64(10) . . ? F40 Si34 F37 178.73(12) . 1 ? F39 Si34 F37 88.44(12) . 1 ? F38 Si34 F37 89.69(11) . 1 ? F36 Si34 F37 88.99(11) 1 1 ? F36 Si34 F37 88.99(11) . 1 ? F40 Si34 F37 178.73(12) . . ? F39 Si34 F37 88.44(12) . . ? F38 Si34 F37 89.69(11) . . ? F36 Si34 F37 88.99(11) 1 . ? F36 Si34 F37 88.99(11) . . ? F40 Si34 F35 90.05(10) . 1 ? F39 Si34 F35 90.56(11) . 1 ? F38 Si34 F35 178.26(11) . 1 ? F36 Si34 F35 88.73(10) 1 1 ? F36 Si34 F35 88.73(10) . 1 ? F37 Si34 F35 88.68(10) 1 1 ? F37 Si34 F35 88.68(10) . 1 ? F40 Si34 F35 90.05(10) . . ? F39 Si34 F35 90.56(11) . . ? F38 Si34 F35 178.26(11) . . ? F36 Si34 F35 88.73(10) 1 . ? F36 Si34 F35 88.73(10) . . ? F37 Si34 F35 88.68(10) 1 . ? F37 Si34 F35 88.68(10) . . ? H41A O41 H41B 115.3 . . ? 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 N7 H7 F36 0.86 2.01 2.855(3) 167.1 1 N7 H7 F37 0.86 2.54 3.082(4) 122.3 1 N10 H10 F35 0.86 2.07 2.923(3) 169.8 1 N10 H10 F37 0.86 2.42 2.992(4) 124.2 1 N23 H23 F37 0.86 2.27 2.960(4) 137.8 2_656 N23 H23 F38 0.86 2.19 2.991(3) 155.8 2_656 N26 H26 F37 0.86 2.37 2.969(4) 127.2 2_656 N26 H26 F39 0.86 2.23 3.079(4) 167.5 2_656 O33 H33 F35 0.82 2.00 2.823(3) 178.7 7_556 O41 H41A O25 0.76 2.30 2.894(3) 135.1 1 O41 H41A O9 0.76 2.40 2.974(3) 133.0 1 O41 H41B F40 0.78 2.22 2.978(3) 164.5 7_556 C6 H6 O41 0.93 2.39 3.260(4) 156.4 4_546 C12 H12 O41 0.93 2.58 3.430(4) 152.7 1 C21 H21 F38 0.93 2.51 3.399(4) 159.1 6_556 C22 H22 O41 0.93 2.52 3.400(4) 157.9 4_546 C28 H28 O41 0.93 2.57 3.427(4) 152.9 1 _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 22.50 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.838 _refine_diff_density_min -0.336 _refine_diff_density_rms 0.077 # Attachment '5_kkb510d_FINAL.cif' data_kkb510d _database_code_depnum_ccdc_archive 'CCDC 612485' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H18 Cu N4 O8 S' _chemical_formula_weight 441.90 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting MONOCLINIC _symmetry_space_group_name_H-M P2(1)/C loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.704(4) _cell_length_b 21.708(11) _cell_length_c 12.165(5) _cell_angle_alpha 90.00 _cell_angle_beta 122.77(2) _cell_angle_gamma 90.00 _cell_volume 1710.7(14) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description BLOCK _exptl_crystal_colour BLUE _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.716 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 908 _exptl_absorpt_coefficient_mu 1.450 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.7133 _exptl_absorpt_correction_T_max 0.9181 _exptl_absorpt_process_details 'BRUKER SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART CCD AREA DETECTOR' _diffrn_measurement_method 'PHI-OMEGA SCAN' _diffrn_detector_area_resol_mean 0.3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9427 _diffrn_reflns_av_R_equivalents 0.0768 _diffrn_reflns_av_sigmaI/netI 0.1022 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 28.11 _reflns_number_total 3849 _reflns_number_gt 2175 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER AXS SMART 3' _computing_cell_refinement 'BRUKER AXS SMART 3' _computing_data_reduction 'BRUKER AXS SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'BRUKER SHELXLTL' _computing_publication_material 'MERCURY 1.4' _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^)+(0.0586P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3849 _refine_ls_number_parameters 247 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0942 _refine_ls_R_factor_gt 0.0472 _refine_ls_wR_factor_ref 0.1230 _refine_ls_wR_factor_gt 0.1060 _refine_ls_goodness_of_fit_ref 0.902 _refine_ls_restrained_S_all 0.902 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.82859(8) 0.20666(2) 0.51346(4) 0.02625(16) Uani 1 1 d . . . N1 N 0.8885(5) 0.11882(14) 0.5780(3) 0.0298(8) Uani 1 1 d . . . C2 C 0.7667(7) 0.07285(17) 0.5013(4) 0.0304(9) Uani 1 1 d . . . H2 H 0.6547 0.0822 0.4181 0.037 Uiso 1 1 calc R . . C3 C 0.8026(7) 0.01136(17) 0.5420(4) 0.0298(10) Uani 1 1 d . . . C4 C 0.9734(7) -0.00140(18) 0.6658(4) 0.0382(11) Uani 1 1 d . . . H4 H 1.0041 -0.0418 0.6959 0.046 Uiso 1 1 calc R . . C5 C 1.0964(8) 0.04623(19) 0.7434(4) 0.0460(13) Uani 1 1 d . . . H5 H 1.2103 0.0382 0.8267 0.055 Uiso 1 1 calc R . . C6 C 1.0508(7) 0.10572(19) 0.6976(4) 0.0398(11) Uani 1 1 d . . . H6 H 1.1348 0.1376 0.7509 0.048 Uiso 1 1 calc R . . N7 N 0.6804(6) -0.03833(14) 0.4661(3) 0.0363(9) Uani 1 1 d . . . H7 H 0.7090 -0.0733 0.5052 0.044 Uiso 1 1 calc R . . C8 C 0.5219(7) -0.03833(18) 0.3381(4) 0.0341(10) Uani 1 1 d . . . O9 O 0.4445(5) 0.00828(12) 0.2708(3) 0.0443(8) Uani 1 1 d . . . N10 N 0.4587(6) -0.09715(14) 0.2921(3) 0.0408(10) Uani 1 1 d . . . H10 H 0.5206 -0.1263 0.3480 0.049 Uiso 1 1 calc R . . C11 C 0.3047(6) -0.11540(17) 0.1647(4) 0.0292(9) Uani 1 1 d . . . C12 C 0.1517(7) -0.07797(19) 0.0695(4) 0.0388(11) Uani 1 1 d . . . H12 H 0.1444 -0.0366 0.0861 0.047 Uiso 1 1 calc R . . C13 C 0.0097(7) -0.10343(18) -0.0509(4) 0.0389(11) Uani 1 1 d . . . H13 H -0.0939 -0.0790 -0.1164 0.047 Uiso 1 1 calc R . . C14 C 0.0214(7) -0.16479(19) -0.0740(4) 0.0355(10) Uani 1 1 d . . . H14 H -0.0752 -0.1812 -0.1556 0.043 Uiso 1 1 calc R . . N15 N 0.1695(5) -0.20213(13) 0.0186(3) 0.0271(8) Uani 1 1 d . . . C16 C 0.3062(7) -0.17712(17) 0.1336(4) 0.0288(9) Uani 1 1 d . . . H16 H 0.4093 -0.2024 0.1973 0.035 Uiso 1 1 calc R . . O17 O 0.5117(5) 0.19166(15) 0.3496(3) 0.0394(8) Uani 1 1 d . . . H17A H 0.5100 0.1879 0.2820 0.059 Uiso 1 1 calc R . . O18 O 0.7744(5) 0.22495(15) 0.6530(3) 0.0383(8) Uani 1 1 d . . . H18A H 0.8845 0.2287 0.7234 0.057 Uiso 1 1 calc R . . O19 O 0.9203(4) 0.18699(12) 0.3916(2) 0.0332(7) Uani 1 1 d . . . S20 S 1.14041(17) 0.20202(5) 0.44423(10) 0.0304(3) Uani 1 1 d . . . O21 O 1.2523(5) 0.20504(14) 0.5856(3) 0.0473(8) Uani 1 1 d . . . O22 O 1.1498(5) 0.26186(12) 0.3888(3) 0.0379(7) Uani 1 1 d . . . O23 O 1.2236(5) 0.15283(13) 0.4010(3) 0.0456(8) Uani 1 1 d . . . O24 O 0.4937(6) 0.31779(15) 0.6083(3) 0.0574(10) Uani 1 1 d . . . H24 H 0.3933 0.3044 0.5405 0.086 Uiso 1 1 calc R . . C25 C 0.5255(9) 0.3801(2) 0.5904(5) 0.0697(16) Uani 1 1 d . . . H25A H 0.5361 0.3837 0.5156 0.105 Uiso 1 1 calc R . . H25B H 0.6507 0.3946 0.6667 0.105 Uiso 1 1 calc R . . H25C H 0.4113 0.4044 0.5769 0.105 Uiso 1 1 calc R . . H17B H 0.406(6) 0.1852(17) 0.355(3) 0.023(11) Uiso 1 1 d . . . H18B H 0.697(9) 0.255(3) 0.645(5) 0.08(2) Uiso 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 0.0286(3) 0.0205(2) 0.0277(3) -0.0001(2) 0.0139(2) -0.0009(2) N1 0.034(2) 0.0220(17) 0.033(2) -0.0052(14) 0.0185(18) -0.0039(16) C2 0.032(2) 0.027(2) 0.028(2) 0.0000(17) 0.013(2) 0.002(2) C3 0.039(3) 0.022(2) 0.032(2) -0.0059(17) 0.022(2) -0.0056(19) C4 0.046(3) 0.024(2) 0.032(2) 0.0046(18) 0.013(2) 0.002(2) C5 0.053(3) 0.030(2) 0.030(2) 0.0031(19) 0.006(2) -0.001(2) C6 0.044(3) 0.028(2) 0.032(2) -0.0020(19) 0.011(2) -0.006(2) N7 0.048(3) 0.0168(16) 0.0282(19) 0.0023(14) 0.0098(19) 0.0011(16) C8 0.041(3) 0.022(2) 0.036(2) -0.0005(18) 0.018(2) -0.002(2) O9 0.051(2) 0.0233(16) 0.0376(18) 0.0034(13) 0.0104(17) 0.0015(15) N10 0.050(3) 0.0201(17) 0.0272(19) 0.0014(14) 0.0040(19) 0.0001(17) C11 0.030(3) 0.025(2) 0.026(2) -0.0003(17) 0.011(2) -0.0006(19) C12 0.046(3) 0.022(2) 0.039(3) 0.0015(19) 0.017(2) 0.004(2) C13 0.036(3) 0.032(2) 0.033(2) 0.0093(19) 0.009(2) 0.013(2) C14 0.033(3) 0.034(2) 0.027(2) 0.0011(19) 0.008(2) 0.002(2) N15 0.026(2) 0.0214(16) 0.0274(17) -0.0020(14) 0.0100(16) -0.0019(15) C16 0.031(3) 0.020(2) 0.029(2) 0.0073(17) 0.012(2) 0.0061(18) O17 0.0277(18) 0.054(2) 0.0365(17) -0.0009(15) 0.0173(16) -0.0092(16) O18 0.049(2) 0.0327(17) 0.0348(17) -0.0042(15) 0.0240(17) -0.0006(17) O19 0.0282(17) 0.0367(16) 0.0375(16) -0.0006(13) 0.0197(15) 0.0009(13) S20 0.0272(6) 0.0297(5) 0.0348(6) 0.0098(4) 0.0171(5) 0.0041(5) O21 0.035(2) 0.059(2) 0.0383(17) 0.0090(15) 0.0138(16) -0.0044(17) O22 0.0417(19) 0.0271(15) 0.0374(16) 0.0097(13) 0.0165(15) 0.0004(14) O23 0.051(2) 0.0345(17) 0.073(2) 0.0163(15) 0.048(2) 0.0133(15) O24 0.053(3) 0.044(2) 0.052(2) -0.0056(16) 0.0135(19) -0.0033(18) C25 0.073(4) 0.065(4) 0.081(4) 0.008(3) 0.048(4) 0.001(3) _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 O18 1.995(3) . ? Cu1 O19 2.003(3) . ? Cu1 N1 2.018(3) . ? Cu1 N15 2.019(3) 2_655 ? Cu1 O17 2.184(3) . ? N1 C6 1.338(5) . ? N1 C2 1.341(5) . ? C2 C3 1.398(5) . ? C2 H2 0.9300 . ? C3 C4 1.389(6) . ? C3 N7 1.401(5) . ? C4 C5 1.375(6) . ? C4 H4 0.9300 . ? C5 C6 1.375(5) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? N7 C8 1.363(5) . ? N7 H7 0.8600 . ? C8 O9 1.233(4) . ? C8 N10 1.373(5) . ? N10 C11 1.406(5) . ? N10 H10 0.8600 . ? C11 C12 1.383(6) . ? C11 C16 1.394(5) . ? C12 C13 1.383(5) . ? C12 H12 0.9300 . ? C13 C14 1.374(5) . ? C13 H13 0.9300 . ? C14 N15 1.356(5) . ? C14 H14 0.9300 . ? N15 C16 1.329(5) . ? N15 Cu1 2.019(3) 2_645 ? C16 H16 0.9300 . ? O17 H17A 0.8200 . ? O17 H17B 0.86(4) . ? O18 H18A 0.8200 . ? O18 H18B 0.85(5) . ? O19 S20 1.489(3) . ? S20 O21 1.450(3) . ? S20 O23 1.481(3) . ? S20 O22 1.483(3) . ? O24 C25 1.412(6) . ? O24 H24 0.8200 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O18 Cu1 O19 172.77(13) . . ? O18 Cu1 N1 88.03(13) . . ? O19 Cu1 N1 89.36(12) . . ? O18 Cu1 N15 89.76(13) . 2_655 ? O19 Cu1 N15 91.37(12) . 2_655 ? N1 Cu1 N15 167.79(14) . 2_655 ? O18 Cu1 O17 99.25(14) . . ? O19 Cu1 O17 87.76(12) . . ? N1 Cu1 O17 96.97(13) . . ? N15 Cu1 O17 95.24(13) 2_655 . ? C6 N1 C2 119.2(3) . . ? C6 N1 Cu1 120.4(3) . . ? C2 N1 Cu1 120.4(3) . . ? N1 C2 C3 122.3(4) . . ? N1 C2 H2 118.9 . . ? C3 C2 H2 118.9 . . ? C4 C3 C2 117.6(4) . . ? C4 C3 N7 117.7(3) . . ? C2 C3 N7 124.6(4) . . ? C5 C4 C3 119.4(4) . . ? C5 C4 H4 120.3 . . ? C3 C4 H4 120.3 . . ? C6 C5 C4 119.9(4) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? N1 C6 C5 121.6(4) . . ? N1 C6 H6 119.2 . . ? C5 C6 H6 119.2 . . ? C8 N7 C3 128.3(3) . . ? C8 N7 H7 115.8 . . ? C3 N7 H7 115.8 . . ? O9 C8 N7 124.8(4) . . ? O9 C8 N10 123.7(4) . . ? N7 C8 N10 111.5(3) . . ? C8 N10 C11 127.8(3) . . ? C8 N10 H10 116.1 . . ? C11 N10 H10 116.1 . . ? C12 C11 C16 117.8(4) . . ? C12 C11 N10 125.8(4) . . ? C16 C11 N10 116.4(3) . . ? C11 C12 C13 118.6(4) . . ? C11 C12 H12 120.7 . . ? C13 C12 H12 120.7 . . ? C14 C13 C12 120.1(4) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? N15 C14 C13 121.9(4) . . ? N15 C14 H14 119.1 . . ? C13 C14 H14 119.1 . . ? C16 N15 C14 117.5(3) . . ? C16 N15 Cu1 121.3(3) . 2_645 ? C14 N15 Cu1 121.1(3) . 2_645 ? N15 C16 C11 124.1(4) . . ? N15 C16 H16 118.0 . . ? C11 C16 H16 118.0 . . ? Cu1 O17 H17A 109.5 . . ? Cu1 O17 H17B 126(2) . . ? H17A O17 H17B 123.8 . . ? Cu1 O18 H18A 109.5 . . ? Cu1 O18 H18B 121(3) . . ? H18A O18 H18B 108.2 . . ? S20 O19 Cu1 114.29(15) . . ? O21 S20 O23 111.13(19) . . ? O21 S20 O22 110.84(17) . . ? O23 S20 O22 109.47(18) . . ? O21 S20 O19 109.10(18) . . ? O23 S20 O19 107.49(18) . . ? O22 S20 O19 108.72(17) . . ? C25 O24 H24 109.5 . . ? O24 C25 H25A 109.5 . . ? O24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? O24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? 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 N7 H7 O23 0.86 1.98 2.836(4) 178.7 3_756 N10 H10 O21 0.86 2.26 3.012(5) 146.2 3_756 O17 H17A O24 0.82 2.05 2.871(5) 176.8 4_565 O17 H17B O23 0.86(4) 1.91(4) 2.744(4) 163(4) 1_455 O18 H18A O22 0.82 1.95 2.774(4) 178.7 4_566 O18 H18B O24 0.80(5) 1.99(5) 2.787(5) 171(6) 1 O24 H24 O22 0.82 2.01 2.822(4) 172.4 1_455 C16 H16 O21 0.93 2.51 3.321(5) 145.2 3_756 _diffrn_measured_fraction_theta_max 0.924 _diffrn_reflns_theta_full 28.11 _diffrn_measured_fraction_theta_full 0.924 _refine_diff_density_max 0.923 _refine_diff_density_min -0.618 _refine_diff_density_rms 0.115 # Attachment '6_kkb446dm_FINAL.cif' data_kkb446dm _database_code_depnum_ccdc_archive 'CCDC 612486' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H16 Cu N6 O10' _chemical_formula_weight 455.84 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting TRICLINIC _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.3292(7) _cell_length_b 9.7989(8) _cell_length_c 13.155(1) _cell_angle_alpha 80.124(1) _cell_angle_beta 74.892(1) _cell_angle_gamma 88.202(1) _cell_volume 1021.11(4) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description PLATE _exptl_crystal_colour 'BLUISH GREEN' _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.483 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 466 _exptl_absorpt_coefficient_mu 1.128 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.6869 _exptl_absorpt_correction_T_max 0.9354 _exptl_absorpt_process_details 'BRUKER SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART CCD AREA DETECTOR' _diffrn_measurement_method 'PHI-OMEGA SCAN' _diffrn_detector_area_resol_mean 0.3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6085 _diffrn_reflns_av_R_equivalents 0.0158 _diffrn_reflns_av_sigmaI/netI 0.0353 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 28.20 _reflns_number_total 4444 _reflns_number_gt 3765 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER AXS SMART 3' _computing_cell_refinement 'BRUKER AXS SMART 3' _computing_data_reduction 'BRUKER AXS SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'BRUKER SHELXLTL' _computing_publication_material 'MERCURY 1.4' _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^)+(0.0896P)^2^+0.2829P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4444 _refine_ls_number_parameters 263 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0495 _refine_ls_R_factor_gt 0.0428 _refine_ls_wR_factor_ref 0.1394 _refine_ls_wR_factor_gt 0.1307 _refine_ls_goodness_of_fit_ref 1.108 _refine_ls_restrained_S_all 1.108 _refine_ls_shift/su_max 0.042 _refine_ls_shift/su_mean 0.001 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 0.5000 0.5000 0.5000 0.01972(14) Uani 1 2 d S . . Cu2 Cu 1.0000 0.0000 0.0000 0.02043(14) Uani 1 2 d S . . N1 N 0.3505(3) 0.5273(2) 0.39918(17) 0.0215(5) Uani 1 1 d . . . C2 C 0.2143(3) 0.6067(3) 0.4195(2) 0.0289(6) Uani 1 1 d . . . H2 H 0.1905 0.6499 0.4810 0.035 Uiso 1 1 calc R . . C3 C 0.1092(4) 0.6266(4) 0.3533(2) 0.0314(6) Uani 1 1 d . . . H3 H 0.0136 0.6824 0.3695 0.038 Uiso 1 1 calc R . . C4 C 0.1433(3) 0.5650(3) 0.2631(2) 0.0249(6) Uani 1 1 d . . . H4 H 0.0716 0.5778 0.2167 0.030 Uiso 1 1 calc R . . C5 C 0.2843(3) 0.4841(3) 0.2414(2) 0.0202(5) Uani 1 1 d . . . C6 C 0.3852(3) 0.4686(3) 0.3115(2) 0.0209(5) Uani 1 1 d . . . H6 H 0.4824 0.4143 0.2966 0.025 Uiso 1 1 calc R . . N7 N 0.3191(3) 0.4270(2) 0.14708(17) 0.0218(5) Uani 1 1 d . . . H7 H 0.2629 0.4596 0.1002 0.026 Uiso 1 1 calc R . . C8 C 0.4316(3) 0.3260(3) 0.1209(2) 0.0187(5) Uani 1 1 d . . . O9 O 0.5134(2) 0.2660(2) 0.17991(14) 0.0237(4) Uani 1 1 d . . . N10 N 0.4457(3) 0.2997(2) 0.01973(17) 0.0206(4) Uani 1 1 d . . . H10 H 0.3797 0.3456 -0.0162 0.025 Uiso 1 1 calc R . . C11 C 0.5554(3) 0.2065(3) -0.0316(2) 0.0196(5) Uani 1 1 d . . . C12 C 0.5312(3) 0.1720(3) -0.1249(2) 0.0249(6) Uani 1 1 d . . . H12 H 0.4406 0.2093 -0.1516 0.030 Uiso 1 1 calc R . . C13 C 0.6407(3) 0.0826(3) -0.1784(2) 0.0286(6) Uani 1 1 d . . . H13 H 0.6249 0.0570 -0.2416 0.034 Uiso 1 1 calc R . . C14 C 0.7724(3) 0.0313(3) -0.1393(2) 0.0266(6) Uani 1 1 d . . . H14 H 0.8468 -0.0303 -0.1761 0.032 Uiso 1 1 calc R . . N15 N 0.7986(3) 0.0662(2) -0.04980(18) 0.0212(4) Uani 1 1 d . . . C16 C 0.6920(3) 0.1506(3) 0.0036(2) 0.0203(5) Uani 1 1 d . . . H16 H 0.7097 0.1732 0.0672 0.024 Uiso 1 1 calc R . . O17 O 1.1590(2) 0.0044(2) -0.18181(16) 0.0289(4) Uani 1 1 d . . . N18 N 1.1991(3) 0.1124(3) -0.24669(19) 0.0291(5) Uani 1 1 d . . . O19 O 1.2572(6) 0.1060(3) -0.3424(2) 0.0992(16) Uani 1 1 d . . . O20 O 1.1786(3) 0.2283(2) -0.22066(17) 0.0348(5) Uani 1 1 d . . . O21 O 1.0686(2) 0.1925(2) 0.00325(18) 0.0282(4) Uani 1 1 d . . . H21 H 1.0837 0.2403 -0.0580 0.042 Uiso 1 1 calc R . . O22 O 0.4808(3) 0.2924(2) 0.51719(17) 0.0301(5) Uani 1 1 d . . . H22B H 0.4132 0.2619 0.5758 0.045 Uiso 1 1 calc R . . O23 O 0.2668(2) 0.5008(3) 0.64358(15) 0.0311(5) Uani 1 1 d . . . H23A H 0.2328 0.5822 0.6450 0.047 Uiso 1 1 calc R . . O24 O 0.1160(3) 0.6349(2) 0.84189(19) 0.0347(5) Uani 1 1 d . . . N25 N 0.1757(3) 0.5544(2) 0.90583(17) 0.0209(4) Uani 1 1 d . . . O26 O 0.2589(2) 0.4525(2) 0.87753(15) 0.0258(4) Uani 1 1 d . . . O27 O 0.1531(2) 0.5759(2) 0.99978(15) 0.0269(4) Uani 1 1 d . . . H21B H 0.992(2) 0.239(2) 0.0431(17) 0.040(10) Uiso 1 1 d . . . H22 H 0.4929 0.2622 0.4726 0.050 Uiso 1 1 d R . . H23B H 0.2860 0.4282 0.6995 0.050 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0195(2) 0.0223(3) 0.0190(2) -0.00698(17) -0.00555(16) 0.00062(17) Cu2 0.0198(2) 0.0139(2) 0.0252(2) -0.00468(17) -0.00102(17) 0.00328(16) N1 0.0186(10) 0.0252(12) 0.0219(10) -0.0092(9) -0.0045(8) 0.0035(9) C2 0.0275(14) 0.0371(16) 0.0256(13) -0.0163(12) -0.0073(11) 0.0104(12) C3 0.0252(13) 0.0413(18) 0.0302(15) -0.0164(13) -0.0064(11) 0.0143(12) C4 0.0224(12) 0.0303(15) 0.0239(13) -0.0093(11) -0.0070(10) 0.0066(11) C5 0.0175(11) 0.0215(13) 0.0216(12) -0.0091(10) -0.0018(9) 0.0020(10) C6 0.0187(11) 0.0235(13) 0.0219(12) -0.0096(10) -0.0040(9) 0.0011(10) N7 0.0214(10) 0.0266(12) 0.0208(10) -0.0104(9) -0.0082(8) 0.0062(9) C8 0.0141(10) 0.0195(12) 0.0223(12) -0.0058(9) -0.0030(9) 0.0003(9) O9 0.0244(9) 0.0262(10) 0.0222(9) -0.0081(7) -0.0071(7) 0.0071(8) N10 0.0211(10) 0.0216(11) 0.0220(10) -0.0092(9) -0.0075(8) 0.0046(8) C11 0.0207(11) 0.0157(12) 0.0210(12) -0.0058(9) -0.0009(9) -0.0011(9) C12 0.0241(13) 0.0265(14) 0.0267(13) -0.0110(11) -0.0065(10) -0.0019(11) C13 0.0271(13) 0.0300(15) 0.0312(14) -0.0154(12) -0.0054(11) 0.0002(11) C14 0.0277(13) 0.0227(13) 0.0284(13) -0.0136(11) 0.0002(11) 0.0015(11) N15 0.0218(10) 0.0157(10) 0.0236(11) -0.0051(8) -0.0003(8) 0.0008(8) C16 0.0211(11) 0.0157(12) 0.0221(12) -0.0036(10) -0.0020(9) -0.0010(9) O17 0.0302(10) 0.0194(10) 0.0282(10) 0.0009(8) 0.0048(8) 0.0028(8) N18 0.0404(13) 0.0212(12) 0.0241(11) -0.0020(9) -0.0061(10) -0.0028(10) O19 0.201(4) 0.0282(15) 0.0327(14) -0.0064(12) 0.036(2) -0.018(2) O20 0.0547(14) 0.0198(10) 0.0328(11) -0.0035(8) -0.0167(10) 0.0003(9) O21 0.0239(9) 0.0157(9) 0.0405(11) -0.0038(8) -0.0008(8) 0.0003(7) O22 0.0371(11) 0.0273(11) 0.0260(10) -0.0101(8) -0.0047(8) -0.0021(9) O23 0.0232(10) 0.0481(13) 0.0219(9) -0.0070(9) -0.0051(8) 0.0034(9) O24 0.0394(11) 0.0227(10) 0.0466(12) 0.0025(9) -0.0253(10) 0.0038(9) N25 0.0200(10) 0.0180(11) 0.0265(11) -0.0073(9) -0.0069(8) -0.0013(8) O26 0.0327(10) 0.0212(10) 0.0237(9) -0.0089(8) -0.0048(8) 0.0043(8) O27 0.0229(9) 0.0325(11) 0.0302(10) -0.0199(9) -0.0060(7) 0.0013(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O22 2.014(2) 2_666 ? Cu1 O22 2.014(2) . ? Cu1 N1 2.024(2) 2_666 ? Cu1 N1 2.024(2) . ? Cu1 O23 2.3308(19) 2_666 ? Cu1 O23 2.3308(19) . ? Cu2 O21 1.999(2) 2_755 ? Cu2 O21 1.999(2) . ? Cu2 N15 2.006(2) 2_755 ? Cu2 N15 2.006(2) . ? Cu2 O17 2.4068(19) 2_755 ? Cu2 O17 2.4068(19) . ? N1 C6 1.338(3) . ? N1 C2 1.349(4) . ? C2 C3 1.375(4) . ? C2 H2 0.9500 . ? C3 C4 1.383(4) . ? C3 H3 0.9500 . ? C4 C5 1.391(4) . ? C4 H4 0.9500 . ? C5 C6 1.388(4) . ? C5 N7 1.406(3) . ? C6 H6 0.9500 . ? N7 C8 1.366(3) . ? N7 H7 0.8800 . ? C8 O9 1.227(3) 1 ? C8 O9 1.227(3) . ? C8 N10 1.374(3) . ? N10 C11 1.401(3) . ? N10 H10 0.8800 . ? C11 C12 1.391(4) . ? C11 C16 1.400(4) . ? C12 C13 1.386(4) . ? C12 H12 0.9500 . ? C13 C14 1.376(4) . ? C13 H13 0.9500 . ? C14 N15 1.352(4) . ? C14 H14 0.9500 . ? N15 C16 1.339(3) . ? C16 H16 0.9500 . ? O17 N18 1.234(3) . ? N18 O20 1.236(3) 1 ? N18 O20 1.236(3) . ? N18 O19 1.237(3) . ? O21 H21 0.8400 . ? O21 H21B 0.88(2) . ? O22 H22B 0.8400 . ? O22 H22 0.6854 . ? O23 H23A 0.8400 . ? O23 H23B 0.9735 . ? O24 N25 1.243(3) . ? N25 O26 1.251(3) 1 ? N25 O26 1.251(3) . ? N25 O27 1.254(3) . ? 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 O22 Cu1 O22 179.999(1) 2_666 . ? O22 Cu1 N1 91.58(9) 2_666 2_666 ? O22 Cu1 N1 88.42(9) . 2_666 ? O22 Cu1 N1 88.42(9) 2_666 . ? O22 Cu1 N1 91.58(9) . . ? N1 Cu1 N1 180.00(8) 2_666 . ? O22 Cu1 O23 90.07(9) 2_666 2_666 ? O22 Cu1 O23 89.93(9) . 2_666 ? N1 Cu1 O23 89.49(8) 2_666 2_666 ? N1 Cu1 O23 90.51(8) . 2_666 ? O22 Cu1 O23 89.93(9) 2_666 . ? O22 Cu1 O23 90.07(9) . . ? N1 Cu1 O23 90.51(8) 2_666 . ? N1 Cu1 O23 89.49(8) . . ? O23 Cu1 O23 180.000(1) 2_666 . ? O21 Cu2 O21 180.0 2_755 . ? O21 Cu2 N15 92.49(9) 2_755 2_755 ? O21 Cu2 N15 87.51(9) . 2_755 ? O21 Cu2 N15 87.52(9) 2_755 . ? O21 Cu2 N15 92.49(9) . . ? N15 Cu2 N15 180.0 2_755 . ? O21 Cu2 O17 93.57(8) 2_755 2_755 ? O21 Cu2 O17 86.43(8) . 2_755 ? N15 Cu2 O17 90.63(8) 2_755 2_755 ? N15 Cu2 O17 89.37(8) . 2_755 ? O21 Cu2 O17 86.43(8) 2_755 . ? O21 Cu2 O17 93.57(8) . . ? N15 Cu2 O17 89.37(8) 2_755 . ? N15 Cu2 O17 90.63(8) . . ? O17 Cu2 O17 180.00(11) 2_755 . ? C6 N1 C2 119.0(2) . . ? C6 N1 Cu1 120.99(18) . . ? C2 N1 Cu1 120.04(18) . . ? N1 C2 C3 121.7(3) . . ? N1 C2 H2 119.2 . . ? C3 C2 H2 119.2 . . ? C2 C3 C4 119.7(3) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C3 C4 C5 118.8(3) . . ? C3 C4 H4 120.6 . . ? C5 C4 H4 120.6 . . ? C6 C5 C4 118.5(2) . . ? C6 C5 N7 123.9(2) . . ? C4 C5 N7 117.6(2) . . ? N1 C6 C5 122.4(2) . . ? N1 C6 H6 118.8 . . ? C5 C6 H6 118.8 . . ? C8 N7 C5 126.5(2) . . ? C8 N7 H7 116.8 . . ? C5 N7 H7 116.8 . . ? O9 C8 N7 124.4(2) 1 . ? O9 C8 N7 124.4(2) . . ? O9 C8 N10 123.1(2) 1 . ? O9 C8 N10 123.1(2) . . ? N7 C8 N10 112.5(2) . . ? C8 N10 C11 126.0(2) . . ? C8 N10 H10 117.0 . . ? C11 N10 H10 117.0 . . ? C12 C11 C16 118.2(2) . . ? C12 C11 N10 118.3(2) . . ? C16 C11 N10 123.4(2) . . ? C13 C12 C11 119.3(3) . . ? C13 C12 H12 120.4 . . ? C11 C12 H12 120.4 . . ? C14 C13 C12 119.5(3) . . ? C14 C13 H13 120.3 . . ? C12 C13 H13 120.3 . . ? N15 C14 C13 121.6(3) . . ? N15 C14 H14 119.2 . . ? C13 C14 H14 119.2 . . ? C16 N15 C14 119.4(2) . . ? C16 N15 Cu2 119.77(18) . . ? C14 N15 Cu2 120.79(18) . . ? N15 C16 C11 122.0(2) . . ? N15 C16 H16 119.0 . . ? C11 C16 H16 119.0 . . ? N18 O17 Cu2 123.32(17) . . ? O17 N18 O20 122.6(2) . 1 ? O17 N18 O20 122.6(2) . . ? O17 N18 O19 119.4(3) . . ? O20 N18 O19 117.9(2) 1 . ? O20 N18 O19 117.9(2) . . ? Cu2 O21 H21 109.5 . . ? Cu2 O21 H21B 114.3(14) . . ? H21 O21 H21B 103.1 . . ? Cu1 O22 H22B 109.5 . . ? Cu1 O22 H22 119.2 . . ? H22B O22 H22 123.6 . . ? Cu1 O23 H23A 109.5 . . ? Cu1 O23 H23B 105.1 . . ? H23A O23 H23B 131.7 . . ? O24 N25 O26 120.8(2) . 1 ? O24 N25 O26 120.8(2) . . ? O24 N25 O27 119.6(2) . . ? O26 N25 O27 119.6(2) 1 . ? O26 N25 O27 119.6(2) . . ? 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 N7 H7 O27 0.88 1.98 2.845(3) 166.4 1_554 N10 H10 O26 0.88 2.06 2.928(3) 170.2 1_554 O21 H21B O24 0.88(2) 2.12(2) 2.960(3) 158.8(19) 2_666 O21 H21B O27 0.88(2) 2.22(2) 2.882(3) 131.3(18) 2_666 O21 H21 O26 0.84 2.47 3.030(3) 124.6 1_654 O22 H22B O19 0.84 2.00 2.735(4) 145.2 1_456 O23 H23B O20 0.97 2.16 2.943(3) 136.8 1_456 O23 H23B O26 0.97 2.35 3.016(3) 125.3 1 C12 H12 O20 0.95 2.56 3.479(4) 161.8 1_455 _diffrn_measured_fraction_theta_max 0.887 _diffrn_reflns_theta_full 28.20 _diffrn_measured_fraction_theta_full 0.887 _refine_diff_density_max 0.985 _refine_diff_density_min -0.787 _refine_diff_density_rms 0.122