# Supplementary Material (ESI) for Chemical Science # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 1475 loop_ _publ_author_name 'Scott, Lauren' 'Telpoukhovskaia, Maria' 'Rodriguez-Rodriguez, Cristina' 'Merkel, Michael' 'Bowen, Meryn' 'Page, Brent' 'Green, David' 'Storr, Tim' 'Thomas, Fancy' 'Allen, David' 'Lockman, Paul' 'Patrick, Brian' 'Adam, Michael J.' 'Orvig, Chris' _publ_contact_author_name 'Orvig, Chris' _publ_contact_author_email orvig@chem.ubc.ca _publ_section_title ; N-Aryl-substituted 3-(b-D-glucopyranosyloxy)-2-methyl-4(1H)- pyridinones as agents for Alzheimer's therapy ; # Attachment '- co318-CuL6-TWIN.CIF' data_twin _database_code_depnum_ccdc_archive 'CCDC 798377' #TrackingRef '- co318-CuL6-TWIN.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H20 Br2 Cu N4 O4 S2' _chemical_formula_weight 787.98 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 17.027(3) _cell_length_b 9.5242(19) _cell_length_c 18.442(4) _cell_angle_alpha 90.00 _cell_angle_beta 104.05(3) _cell_angle_gamma 90.00 _cell_volume 2901.4(10) _cell_formula_units_Z 4 _cell_measurement_temperature 173(1) _cell_measurement_reflns_used 3280 _cell_measurement_theta_min 2.47 _cell_measurement_theta_max 21.01 _exptl_crystal_description chip _exptl_crystal_colour yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.804 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1564 _exptl_absorpt_coefficient_mu 3.696 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.445 _exptl_absorpt_correction_T_max 0.691 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(1) _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 X8 APEX II' _diffrn_measurement_method 'area detector' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6289 _diffrn_reflns_av_R_equivalents 0.071 _diffrn_reflns_av_sigmaI/netI 0.1424 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.46 _diffrn_reflns_theta_max 24.99 _reflns_number_total 6289 _reflns_number_gt 3216 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; The material crystallizes as a two-component twin, by 180 degree rotation about the (1,0,1) axis. The refinement was carried out using an HKLF5 format data set containing all the reflections from the larger component, and only those from the sweaker component that overlap with a reflection from the major component. 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^)+(0.0515P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6289 _refine_ls_number_parameters 394 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1035 _refine_ls_R_factor_gt 0.0497 _refine_ls_wR_factor_ref 0.1182 _refine_ls_wR_factor_gt 0.1119 _refine_ls_goodness_of_fit_ref 0.927 _refine_ls_restrained_S_all 0.927 _refine_ls_shift/su_max 0.012 _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 0.0000 0.5000 0.0000 0.0343(3) Uani 1 2 d S . . O1 O -0.0151(2) 0.4384(4) 0.0963(3) 0.0332(12) Uani 1 1 d . . . O2 O 0.0950(2) 0.5938(4) 0.0562(2) 0.0303(11) Uani 1 1 d . . . Br1 Br 0.54739(5) 0.43898(9) 0.70935(5) 0.0550(3) Uani 1 1 d . . . S1 S 0.22847(12) 0.83238(19) 0.32945(10) 0.0405(5) Uani 1 1 d . . . N1 N 0.1715(3) 0.5892(5) 0.2563(3) 0.0263(13) Uani 1 1 d . . . N2 N 0.2745(3) 0.5819(5) 0.3699(3) 0.0254(14) Uani 1 1 d . . . C1 C 0.2322(4) 0.7102(6) 0.1631(3) 0.0352(19) Uani 1 1 d . . . H1A H 0.2181 0.8100 0.1627 0.053 Uiso 1 1 calc R . . H1B H 0.2381 0.6826 0.1135 0.053 Uiso 1 1 calc R . . H1C H 0.2834 0.6940 0.2002 0.053 Uiso 1 1 calc R . . C2 C 0.1663(4) 0.6243(6) 0.1831(4) 0.0223(16) Uani 1 1 d . . . C3 C 0.1030(4) 0.5707(7) 0.1272(4) 0.0278(17) Uani 1 1 d . . . C4 C 0.0434(4) 0.4831(7) 0.1481(4) 0.0266(17) Uani 1 1 d . . . C5 C 0.0575(5) 0.4474(7) 0.2245(4) 0.0373(19) Uani 1 1 d . . . H5 H 0.0217 0.3837 0.2399 0.045 Uiso 1 1 calc R . . C6 C 0.1171(4) 0.4984(7) 0.2736(4) 0.0258(17) Uani 1 1 d . . . H6 H 0.1236 0.4716 0.3243 0.031 Uiso 1 1 calc R . . C7 C 0.2277(4) 0.6537(7) 0.3158(4) 0.0269(17) Uani 1 1 d . . . C8 C 0.2972(4) 0.8096(7) 0.4114(3) 0.0305(18) Uani 1 1 d . . . H8 H 0.3200 0.8842 0.4440 0.037 Uiso 1 1 calc R . . C9 C 0.3163(4) 0.6702(7) 0.4255(4) 0.0263(17) Uani 1 1 d . . . C10 C 0.3722(4) 0.6138(7) 0.4920(4) 0.0250(17) Uani 1 1 d . . . C11 C 0.4097(4) 0.7009(7) 0.5505(4) 0.0345(19) Uani 1 1 d . . . H11 H 0.3990 0.7989 0.5466 0.041 Uiso 1 1 calc R . . C12 C 0.4627(4) 0.6492(8) 0.6145(4) 0.038(2) Uani 1 1 d . . . H12 H 0.4883 0.7107 0.6537 0.046 Uiso 1 1 calc R . . C13 C 0.4773(4) 0.5061(8) 0.6200(4) 0.0346(19) Uani 1 1 d . . . C14 C 0.4419(4) 0.4155(7) 0.5634(4) 0.0334(18) Uani 1 1 d . . . H14 H 0.4530 0.3177 0.5679 0.040 Uiso 1 1 calc R . . C15 C 0.3902(4) 0.4686(7) 0.5000(4) 0.0342(19) Uani 1 1 d . . . H15 H 0.3660 0.4063 0.4606 0.041 Uiso 1 1 calc R . . Cu2 Cu 0.0000 1.0000 0.5000 0.0365(4) Uani 1 2 d S . . O3 O 0.1070(3) 1.0559(4) 0.4913(2) 0.0370(12) Uani 1 1 d . . . O4 O 0.0543(3) 0.9016(4) 0.5880(2) 0.0308(12) Uani 1 1 d . . . Br2 Br 0.71070(4) 1.08230(9) 1.06703(4) 0.0520(3) Uani 1 1 d . . . S2 S 0.34031(11) 0.65625(18) 0.73895(11) 0.0396(5) Uani 1 1 d . . . N3 N 0.2705(3) 0.8964(5) 0.6707(3) 0.0242(14) Uani 1 1 d . . . N4 N 0.3836(3) 0.9104(5) 0.7751(3) 0.0215(13) Uani 1 1 d . . . C16 C 0.1602(4) 0.7894(6) 0.7216(3) 0.0353(19) Uani 1 1 d . . . H16A H 0.1619 0.6883 0.7121 0.053 Uiso 1 1 calc R . . H16B H 0.1045 0.8172 0.7205 0.053 Uiso 1 1 calc R . . H16C H 0.1953 0.8110 0.7708 0.053 Uiso 1 1 calc R . . C17 C 0.1889(4) 0.8685(6) 0.6623(4) 0.0272(17) Uani 1 1 d . . . C18 C 0.1343(4) 0.9220(7) 0.6006(3) 0.0242(16) Uani 1 1 d . . . C19 C 0.1599(4) 1.0078(7) 0.5460(4) 0.0334(19) Uani 1 1 d . . . C20 C 0.2445(4) 1.0344(7) 0.5613(4) 0.0377(19) Uani 1 1 d . . . H20 H 0.2651 1.0925 0.5284 0.045 Uiso 1 1 calc R . . C21 C 0.2944(4) 0.9802(7) 0.6201(4) 0.0320(18) Uani 1 1 d . . . H21 H 0.3505 1.0005 0.6278 0.038 Uiso 1 1 calc R . . C22 C 0.3300(4) 0.8372(7) 0.7296(4) 0.0261(17) Uani 1 1 d . . . C23 C 0.4234(4) 0.6833(7) 0.8100(4) 0.0347(19) Uani 1 1 d . . . H23 H 0.4554 0.6104 0.8375 0.042 Uiso 1 1 calc R . . C24 C 0.4383(4) 0.8246(7) 0.8228(4) 0.0244(17) Uani 1 1 d . . . C25 C 0.5029(4) 0.8870(7) 0.8810(3) 0.0236(17) Uani 1 1 d . . . C26 C 0.5691(4) 0.8038(7) 0.9205(4) 0.0320(18) Uani 1 1 d . . . H26 H 0.5714 0.7067 0.9093 0.038 Uiso 1 1 calc R . . C27 C 0.6292(4) 0.8634(8) 0.9743(4) 0.036(2) Uani 1 1 d . . . H27 H 0.6728 0.8076 1.0013 0.043 Uiso 1 1 calc R . . C28 C 0.6262(4) 1.0069(8) 0.9897(3) 0.0293(18) Uani 1 1 d . . . C29 C 0.5637(4) 1.0879(7) 0.9522(3) 0.0263(17) Uani 1 1 d . . . H29 H 0.5628 1.1853 0.9632 0.032 Uiso 1 1 calc R . . C30 C 0.5017(4) 1.0292(6) 0.8983(3) 0.0255(17) Uani 1 1 d . . . H30 H 0.4578 1.0862 0.8729 0.031 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0299(7) 0.0360(8) 0.0339(8) -0.0027(7) 0.0018(6) 0.0008(6) O1 0.021(3) 0.031(3) 0.050(3) -0.007(3) 0.011(2) -0.009(2) O2 0.026(3) 0.031(3) 0.029(3) 0.002(2) -0.004(2) 0.000(2) Br1 0.0407(5) 0.0654(6) 0.0523(6) 0.0059(5) -0.0015(4) 0.0074(5) S1 0.0573(14) 0.0219(11) 0.0382(12) -0.0029(10) 0.0037(10) -0.0091(10) N1 0.025(3) 0.029(3) 0.026(3) 0.003(3) 0.009(3) 0.001(3) N2 0.020(3) 0.030(4) 0.028(3) -0.004(3) 0.008(3) -0.006(3) C1 0.037(5) 0.033(5) 0.034(4) 0.004(4) 0.004(4) -0.007(4) C2 0.021(4) 0.014(4) 0.033(5) -0.003(3) 0.008(4) 0.001(3) C3 0.026(4) 0.028(4) 0.027(4) 0.008(4) 0.002(4) 0.011(4) C4 0.024(4) 0.017(4) 0.036(5) -0.004(4) 0.001(4) 0.007(3) C5 0.061(6) 0.027(4) 0.027(5) -0.007(4) 0.018(4) -0.021(4) C6 0.023(4) 0.033(4) 0.023(4) 0.017(4) 0.010(4) 0.007(4) C7 0.029(4) 0.023(4) 0.035(5) -0.010(4) 0.019(4) -0.012(4) C8 0.042(5) 0.027(4) 0.023(4) -0.004(4) 0.009(4) -0.007(4) C9 0.028(4) 0.018(4) 0.038(5) -0.003(4) 0.018(4) -0.010(4) C10 0.017(4) 0.029(5) 0.031(4) -0.003(4) 0.011(3) -0.012(3) C11 0.047(5) 0.023(4) 0.033(5) -0.002(4) 0.008(4) -0.009(4) C12 0.029(5) 0.041(5) 0.044(5) -0.008(4) 0.006(4) -0.016(4) C13 0.015(4) 0.047(5) 0.041(5) 0.004(5) 0.005(4) 0.006(4) C14 0.028(4) 0.029(5) 0.043(5) -0.003(4) 0.009(4) -0.001(4) C15 0.021(4) 0.039(5) 0.043(5) -0.012(4) 0.011(4) -0.010(4) Cu2 0.0332(8) 0.0354(8) 0.0353(8) -0.0031(7) -0.0024(6) 0.0004(6) O3 0.044(3) 0.036(3) 0.029(3) 0.005(2) 0.004(3) 0.005(3) O4 0.032(3) 0.027(3) 0.029(3) -0.002(2) 0.000(2) -0.004(2) Br2 0.0312(5) 0.0800(7) 0.0406(5) -0.0116(5) 0.0003(4) -0.0022(5) S2 0.0417(12) 0.0224(10) 0.0490(13) 0.0046(10) -0.0001(10) -0.0008(10) N3 0.016(3) 0.028(4) 0.029(3) 0.000(3) 0.006(3) 0.000(3) N4 0.016(3) 0.026(3) 0.023(3) -0.005(3) 0.006(3) -0.003(3) C16 0.025(4) 0.032(5) 0.048(5) 0.001(4) 0.006(4) -0.011(3) C17 0.037(5) 0.017(4) 0.027(4) -0.006(3) 0.005(4) -0.003(4) C18 0.023(4) 0.029(4) 0.020(4) -0.010(4) 0.002(3) -0.010(4) C19 0.018(4) 0.029(4) 0.047(5) -0.027(4) -0.004(4) 0.001(4) C20 0.040(5) 0.040(5) 0.031(5) 0.013(4) 0.006(4) 0.007(4) C21 0.026(4) 0.043(5) 0.027(4) 0.000(4) 0.006(4) -0.008(4) C22 0.024(4) 0.026(4) 0.031(4) 0.006(4) 0.013(4) 0.005(4) C23 0.046(5) 0.025(4) 0.034(5) 0.016(4) 0.011(4) 0.007(4) C24 0.021(4) 0.022(4) 0.033(4) 0.011(4) 0.013(4) 0.006(4) C25 0.018(4) 0.033(5) 0.021(4) 0.002(4) 0.008(3) -0.006(3) C26 0.032(5) 0.034(5) 0.033(5) 0.015(4) 0.015(4) 0.008(4) C27 0.026(5) 0.060(6) 0.021(4) 0.019(4) 0.003(4) 0.008(4) C28 0.031(5) 0.036(5) 0.024(4) -0.013(4) 0.013(4) -0.007(4) C29 0.024(4) 0.028(4) 0.027(4) 0.002(4) 0.007(3) 0.006(4) C30 0.033(4) 0.026(5) 0.019(4) 0.005(3) 0.009(3) 0.004(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 O2 1.917(4) 3_565 ? Cu1 O2 1.917(4) . ? Cu1 O1 1.946(4) . ? Cu1 O1 1.946(4) 3_565 ? O1 C4 1.274(7) . ? O2 C3 1.301(7) . ? Br1 C13 1.895(7) . ? S1 C8 1.687(6) . ? S1 C7 1.720(6) . ? N1 C6 1.361(7) . ? N1 C2 1.373(7) . ? N1 C7 1.410(7) . ? N2 C7 1.307(7) . ? N2 C9 1.384(7) . ? C1 C2 1.504(8) . ? C2 C3 1.395(8) . ? C3 C4 1.437(9) . ? C4 C5 1.412(8) . ? C5 C6 1.280(8) . ? C8 C9 1.377(8) . ? C9 C10 1.460(8) . ? C10 C11 1.387(8) . ? C10 C15 1.416(8) . ? C11 C12 1.391(8) . ? C12 C13 1.384(9) . ? C13 C14 1.377(9) . ? C14 C15 1.378(8) . ? Cu2 O4 1.907(4) . ? Cu2 O4 1.907(4) 3_576 ? Cu2 O3 1.942(4) 3_576 ? Cu2 O3 1.942(4) . ? O3 C19 1.265(7) . ? O4 C18 1.338(7) . ? Br2 C28 1.904(6) . ? S2 C23 1.698(7) . ? S2 C22 1.736(6) . ? N3 C21 1.364(7) . ? N3 C17 1.386(7) . ? N3 C22 1.411(7) . ? N4 C22 1.285(7) . ? N4 C24 1.382(7) . ? C16 C17 1.503(8) . ? C17 C18 1.381(8) . ? C18 C19 1.445(9) . ? C19 C20 1.420(9) . ? C20 C21 1.310(8) . ? C23 C24 1.379(8) . ? C24 C25 1.464(8) . ? C25 C30 1.393(8) . ? C25 C26 1.424(8) . ? C26 C27 1.364(8) . ? C27 C28 1.399(9) . ? C28 C29 1.359(8) . ? C29 C30 1.381(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Cu1 O2 180.0(2) 3_565 . ? O2 Cu1 O1 94.15(18) 3_565 . ? O2 Cu1 O1 85.85(18) . . ? O2 Cu1 O1 85.85(18) 3_565 3_565 ? O2 Cu1 O1 94.15(18) . 3_565 ? O1 Cu1 O1 180.0(2) . 3_565 ? C4 O1 Cu1 109.4(4) . . ? C3 O2 Cu1 109.5(4) . . ? C8 S1 C7 89.0(3) . . ? C6 N1 C2 120.0(5) . . ? C6 N1 C7 117.8(5) . . ? C2 N1 C7 121.9(5) . . ? C7 N2 C9 110.9(5) . . ? N1 C2 C3 119.4(6) . . ? N1 C2 C1 120.0(6) . . ? C3 C2 C1 120.4(6) . . ? O2 C3 C2 123.7(6) . . ? O2 C3 C4 117.3(6) . . ? C2 C3 C4 119.0(6) . . ? O1 C4 C5 125.5(6) . . ? O1 C4 C3 117.8(6) . . ? C5 C4 C3 116.6(6) . . ? C6 C5 C4 121.9(6) . . ? C5 C6 N1 122.9(6) . . ? N2 C7 N1 122.6(6) . . ? N2 C7 S1 115.1(5) . . ? N1 C7 S1 121.6(5) . . ? C9 C8 S1 112.0(5) . . ? C8 C9 N2 113.0(6) . . ? C8 C9 C10 126.1(6) . . ? N2 C9 C10 120.8(6) . . ? C11 C10 C15 117.2(6) . . ? C11 C10 C9 121.0(6) . . ? C15 C10 C9 121.8(6) . . ? C10 C11 C12 122.0(6) . . ? C13 C12 C11 118.6(7) . . ? C14 C13 C12 121.6(7) . . ? C14 C13 Br1 121.0(6) . . ? C12 C13 Br1 117.4(6) . . ? C13 C14 C15 119.1(6) . . ? C14 C15 C10 121.6(7) . . ? O4 Cu2 O4 180.000(1) . 3_576 ? O4 Cu2 O3 93.80(18) . 3_576 ? O4 Cu2 O3 86.20(18) 3_576 3_576 ? O4 Cu2 O3 86.20(18) . . ? O4 Cu2 O3 93.80(18) 3_576 . ? O3 Cu2 O3 180.0(2) 3_576 . ? C19 O3 Cu2 109.6(4) . . ? C18 O4 Cu2 109.9(4) . . ? C23 S2 C22 88.3(3) . . ? C21 N3 C17 119.6(6) . . ? C21 N3 C22 118.9(5) . . ? C17 N3 C22 121.5(6) . . ? C22 N4 C24 110.9(5) . . ? C18 C17 N3 118.5(6) . . ? C18 C17 C16 120.7(6) . . ? N3 C17 C16 120.7(6) . . ? O4 C18 C17 123.0(6) . . ? O4 C18 C19 115.3(6) . . ? C17 C18 C19 121.7(6) . . ? O3 C19 C20 125.8(7) . . ? O3 C19 C18 118.9(6) . . ? C20 C19 C18 115.2(7) . . ? C21 C20 C19 121.2(7) . . ? C20 C21 N3 123.7(6) . . ? N4 C22 N3 123.3(6) . . ? N4 C22 S2 115.8(5) . . ? N3 C22 S2 120.6(5) . . ? C24 C23 S2 111.3(5) . . ? C23 C24 N4 113.6(6) . . ? C23 C24 C25 126.6(6) . . ? N4 C24 C25 119.8(6) . . ? C30 C25 C26 118.6(6) . . ? C30 C25 C24 120.8(6) . . ? C26 C25 C24 120.6(6) . . ? C27 C26 C25 120.1(6) . . ? C26 C27 C28 119.7(6) . . ? C29 C28 C27 120.9(6) . . ? C29 C28 Br2 121.5(5) . . ? C27 C28 Br2 117.5(6) . . ? C28 C29 C30 120.2(6) . . ? C29 C30 C25 120.5(6) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.922 _refine_diff_density_min -0.582 _refine_diff_density_rms 0.104 # Attachment '- co335-HL1-new4pub.cif' data_co335 _database_code_depnum_ccdc_archive 'CCDC 798378' #TrackingRef '- co335-HL1-new4pub.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Hdapp _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H20 N2 O3' _chemical_formula_weight 276.33 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' _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 7.5438(8) _cell_length_b 9.0878(9) _cell_length_c 11.3719(12) _cell_angle_alpha 85.485(6) _cell_angle_beta 78.375(6) _cell_angle_gamma 69.760(5) _cell_volume 716.44(13) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3617 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 27.87 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.281 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 296 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.894 _exptl_absorpt_correction_T_max 0.996 _exptl_absorpt_process_details 'SADABS (Bruker Nonius, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker X8 APEX II' _diffrn_measurement_method 'area deteector' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14821 _diffrn_reflns_av_R_equivalents 0.0323 _diffrn_reflns_av_sigmaI/netI 0.0316 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 28.13 _reflns_number_total 3490 _reflns_number_gt 2533 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0601P)^2^+0.1306P] 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 3490 _refine_ls_number_parameters 193 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0676 _refine_ls_R_factor_gt 0.0459 _refine_ls_wR_factor_ref 0.1281 _refine_ls_wR_factor_gt 0.1173 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _refine_ls_shift/su_max 0.022 _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 C1 C -0.0354(2) 0.39438(19) 0.76236(14) 0.0343(3) Uani 1 1 d . . . H1A H 0.0315 0.4709 0.7545 0.051 Uiso 1 1 calc R . . H1B H 0.0250 0.3064 0.8130 0.051 Uiso 1 1 calc R . . H1C H -0.1706 0.4446 0.7991 0.051 Uiso 1 1 calc R . . C2 C -0.02311(19) 0.33541(16) 0.64102(12) 0.0253(3) Uani 1 1 d . . . C3 C -0.17080(19) 0.39357(15) 0.57936(12) 0.0258(3) Uani 1 1 d . . . C4 C -0.16317(19) 0.33624(16) 0.46415(12) 0.0263(3) Uani 1 1 d . . . C5 C 0.0102(2) 0.21777(18) 0.41738(13) 0.0322(3) Uani 1 1 d . . . H5 H 0.0259 0.1762 0.3404 0.039 Uiso 1 1 calc R . . C6 C 0.1551(2) 0.16217(18) 0.48062(13) 0.0326(3) Uani 1 1 d . . . H6 H 0.2697 0.0817 0.4469 0.039 Uiso 1 1 calc R . . C7 C 0.29628(19) 0.14620(16) 0.65558(12) 0.0253(3) Uani 1 1 d . . . C8 C 0.3218(2) -0.00196(17) 0.70402(13) 0.0291(3) Uani 1 1 d . . . H8 H 0.2423 -0.0580 0.6905 0.035 Uiso 1 1 calc R . . C9 C 0.4623(2) -0.06910(17) 0.77209(13) 0.0299(3) Uani 1 1 d . . . H9 H 0.4784 -0.1712 0.8052 0.036 Uiso 1 1 calc R . . C10 C 0.58166(19) 0.01082(16) 0.79318(12) 0.0252(3) Uani 1 1 d . . . C11 C 0.5549(2) 0.16000(16) 0.74017(13) 0.0278(3) Uani 1 1 d . . . H11 H 0.6355 0.2163 0.7513 0.033 Uiso 1 1 calc R . . C12 C 0.4144(2) 0.22631(16) 0.67239(13) 0.0288(3) Uani 1 1 d . . . H12 H 0.3989 0.3273 0.6372 0.035 Uiso 1 1 calc R . . C13 C 0.7306(2) -0.19952(19) 0.92735(15) 0.0404(4) Uani 1 1 d . . . H13A H 0.6112 -0.1832 0.9861 0.061 Uiso 1 1 calc R . . H13B H 0.8398 -0.2306 0.9692 0.061 Uiso 1 1 calc R . . H13C H 0.7471 -0.2824 0.8718 0.061 Uiso 1 1 calc R . . C14 C 0.8387(2) 0.0294(2) 0.88660(17) 0.0441(4) Uani 1 1 d . . . H14A H 0.8850 0.0789 0.8127 0.066 Uiso 1 1 calc R . . H14B H 0.9487 -0.0431 0.9185 0.066 Uiso 1 1 calc R . . H14C H 0.7620 0.1104 0.9461 0.066 Uiso 1 1 calc R . . C15 C -0.3171(3) 0.4383(2) 0.10181(15) 0.0500(5) Uani 1 1 d . . . H15A H -0.4546 0.4611 0.1333 0.075 Uiso 1 1 calc R . . H15B H -0.2868 0.4022 0.0188 0.075 Uiso 1 1 calc R . . H15C H -0.2848 0.5335 0.1040 0.075 Uiso 1 1 calc R . . N1 N 0.14098(16) 0.21796(14) 0.59010(10) 0.0264(3) Uani 1 1 d . . . N2 N 0.72161(19) -0.05551(15) 0.86083(12) 0.0355(3) Uani 1 1 d . . . O1 O -0.30534(14) 0.39286(12) 0.41058(9) 0.0328(3) Uani 1 1 d . . . O2 O -0.33095(15) 0.50904(12) 0.63044(10) 0.0356(3) Uani 1 1 d . . . O3 O -0.21082(18) 0.32174(14) 0.17193(11) 0.0449(3) Uani 1 1 d . . . H2O H -0.418(3) 0.526(2) 0.5830(18) 0.060(6) Uiso 1 1 d . . . H3O H -0.252(3) 0.352(2) 0.250(2) 0.071(7) 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 C1 0.0289(8) 0.0391(8) 0.0327(8) -0.0081(6) -0.0076(6) -0.0062(6) C2 0.0226(7) 0.0259(7) 0.0264(7) -0.0001(5) -0.0033(5) -0.0078(5) C3 0.0214(7) 0.0247(7) 0.0287(7) 0.0001(5) -0.0026(6) -0.0058(5) C4 0.0231(7) 0.0299(7) 0.0261(7) 0.0057(5) -0.0069(5) -0.0092(6) C5 0.0283(8) 0.0391(8) 0.0253(7) -0.0046(6) -0.0068(6) -0.0048(6) C6 0.0256(7) 0.0382(8) 0.0280(7) -0.0062(6) -0.0042(6) -0.0024(6) C7 0.0201(7) 0.0287(7) 0.0248(7) -0.0003(5) -0.0061(5) -0.0043(5) C8 0.0256(7) 0.0292(7) 0.0347(8) -0.0001(6) -0.0073(6) -0.0110(6) C9 0.0292(7) 0.0257(7) 0.0346(8) 0.0049(6) -0.0080(6) -0.0091(6) C10 0.0215(7) 0.0271(7) 0.0235(7) -0.0026(5) -0.0029(5) -0.0041(5) C11 0.0245(7) 0.0282(7) 0.0324(7) -0.0002(6) -0.0073(6) -0.0101(6) C12 0.0281(7) 0.0258(7) 0.0324(7) 0.0038(6) -0.0067(6) -0.0093(6) C13 0.0349(9) 0.0400(9) 0.0397(9) 0.0089(7) -0.0126(7) -0.0035(7) C14 0.0373(9) 0.0455(10) 0.0541(11) -0.0023(8) -0.0246(8) -0.0104(8) C15 0.0670(13) 0.0448(10) 0.0335(9) 0.0035(7) -0.0139(9) -0.0113(9) N1 0.0216(6) 0.0305(6) 0.0257(6) -0.0003(5) -0.0064(5) -0.0057(5) N2 0.0342(7) 0.0355(7) 0.0398(7) 0.0065(6) -0.0186(6) -0.0103(6) O1 0.0261(5) 0.0387(6) 0.0314(5) 0.0027(4) -0.0116(4) -0.0051(4) O2 0.0257(5) 0.0369(6) 0.0384(6) -0.0091(5) -0.0101(5) 0.0007(4) O3 0.0455(7) 0.0427(7) 0.0369(7) 0.0002(5) -0.0073(5) -0.0034(5) _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 C1 C2 1.494(2) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.3644(19) . ? C2 N1 1.3788(17) . ? C3 O2 1.3544(16) . ? C3 C4 1.431(2) . ? C4 O1 1.2721(16) . ? C4 C5 1.410(2) . ? C5 C6 1.358(2) . ? C5 H5 0.9500 . ? C6 N1 1.3518(18) . ? C6 H6 0.9500 . ? C7 C8 1.378(2) . ? C7 C12 1.379(2) . ? C7 N1 1.4487(17) . ? C8 C9 1.380(2) . ? C8 H8 0.9500 . ? C9 C10 1.401(2) . ? C9 H9 0.9500 . ? C10 N2 1.3725(18) . ? C10 C11 1.4047(19) . ? C11 C12 1.3765(19) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 N2 1.4466(19) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 N2 1.440(2) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 O3 1.392(2) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? O2 H2O 0.90(2) . ? O3 H3O 0.91(2) . ? 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 C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 C2 N1 118.92(12) . . ? C3 C2 C1 121.80(12) . . ? N1 C2 C1 119.28(12) . . ? O2 C3 C2 118.24(12) . . ? O2 C3 C4 119.19(12) . . ? C2 C3 C4 122.56(12) . . ? O1 C4 C5 124.49(13) . . ? O1 C4 C3 120.35(12) . . ? C5 C4 C3 115.15(12) . . ? C6 C5 C4 121.05(13) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? N1 C6 C5 121.94(13) . . ? N1 C6 H6 119.0 . . ? C5 C6 H6 119.0 . . ? C8 C7 C12 120.08(13) . . ? C8 C7 N1 119.26(12) . . ? C12 C7 N1 120.63(12) . . ? C7 C8 C9 120.19(13) . . ? C7 C8 H8 119.9 . . ? C9 C8 H8 119.9 . . ? C8 C9 C10 121.07(13) . . ? C8 C9 H9 119.5 . . ? C10 C9 H9 119.5 . . ? N2 C10 C9 121.27(12) . . ? N2 C10 C11 121.43(13) . . ? C9 C10 C11 117.29(12) . . ? C12 C11 C10 121.32(13) . . ? C12 C11 H11 119.3 . . ? C10 C11 H11 119.3 . . ? C11 C12 C7 120.00(13) . . ? C11 C12 H12 120.0 . . ? C7 C12 H12 120.0 . . ? N2 C13 H13A 109.5 . . ? N2 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N2 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N2 C14 H14A 109.5 . . ? N2 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N2 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O3 C15 H15A 109.5 . . ? O3 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O3 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C6 N1 C2 120.36(12) . . ? C6 N1 C7 118.86(11) . . ? C2 N1 C7 120.69(11) . . ? C10 N2 C14 121.15(13) . . ? C10 N2 C13 120.47(13) . . ? C14 N2 C13 117.31(13) . . ? C3 O2 H2O 107.1(13) . . ? C15 O3 H3O 108.4(13) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C2 C3 O2 -179.92(12) . . . . ? C1 C2 C3 O2 0.7(2) . . . . ? N1 C2 C3 C4 0.7(2) . . . . ? C1 C2 C3 C4 -178.67(13) . . . . ? O2 C3 C4 O1 -0.2(2) . . . . ? C2 C3 C4 O1 179.19(13) . . . . ? O2 C3 C4 C5 179.11(12) . . . . ? C2 C3 C4 C5 -1.5(2) . . . . ? O1 C4 C5 C6 -179.35(14) . . . . ? C3 C4 C5 C6 1.4(2) . . . . ? C4 C5 C6 N1 -0.5(2) . . . . ? C12 C7 C8 C9 1.7(2) . . . . ? N1 C7 C8 C9 -176.57(12) . . . . ? C7 C8 C9 C10 -0.1(2) . . . . ? C8 C9 C10 N2 179.99(13) . . . . ? C8 C9 C10 C11 -1.3(2) . . . . ? N2 C10 C11 C12 -179.98(13) . . . . ? C9 C10 C11 C12 1.4(2) . . . . ? C10 C11 C12 C7 0.1(2) . . . . ? C8 C7 C12 C11 -1.6(2) . . . . ? N1 C7 C12 C11 176.56(12) . . . . ? C5 C6 N1 C2 -0.4(2) . . . . ? C5 C6 N1 C7 176.12(14) . . . . ? C3 C2 N1 C6 0.3(2) . . . . ? C1 C2 N1 C6 179.69(14) . . . . ? C3 C2 N1 C7 -176.16(12) . . . . ? C1 C2 N1 C7 3.24(19) . . . . ? C8 C7 N1 C6 -71.69(18) . . . . ? C12 C7 N1 C6 110.09(16) . . . . ? C8 C7 N1 C2 104.81(15) . . . . ? C12 C7 N1 C2 -73.41(17) . . . . ? C9 C10 N2 C14 -177.35(14) . . . . ? C11 C10 N2 C14 4.0(2) . . . . ? C9 C10 N2 C13 -9.5(2) . . . . ? C11 C10 N2 C13 171.90(13) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 28.13 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.246 _refine_diff_density_min -0.213 _refine_diff_density_rms 0.044 # Attachment '- co336-HL3-new4pub.cif' data_co336-2 _database_code_depnum_ccdc_archive 'CCDC 798379' #TrackingRef '- co336-HL3-new4pub.cif' _audit_creation_method shelxl-97 _chemical_name_systematic ; ? ; _chemical_name_common Hzapp _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H30 N4 O6' _chemical_formula_weight 482.53 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.9650(17) _cell_length_b 14.3780(18) _cell_length_c 12.9795(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.445(8) _cell_angle_gamma 90.00 _cell_volume 2419.4(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3112 _cell_measurement_theta_min 2.63 _cell_measurement_theta_max 24.21 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.325 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1024 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.842 _exptl_absorpt_correction_T_max 0.993 _exptl_absorpt_process_details 'SADABS (Bruker Nonius, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 X8 APEX II' _diffrn_measurement_method 'area detector' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20040 _diffrn_reflns_av_R_equivalents 0.0438 _diffrn_reflns_av_sigmaI/netI 0.0434 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 25.47 _reflns_number_total 4455 _reflns_number_gt 2879 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0519P)^2^+0.2616P] 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 4455 _refine_ls_number_parameters 355 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0809 _refine_ls_R_factor_gt 0.0430 _refine_ls_wR_factor_ref 0.1124 _refine_ls_wR_factor_gt 0.0952 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _refine_ls_shift/su_max 0.002 _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 c1 c 1.03450(15) -0.05362(16) 0.25979(15) 0.0443(6) uani 1 1 d . . . h1a h 1.0441 0.0112 0.2387 0.067 uiso 1 1 calc r . . h1b h 1.0146 -0.0911 0.1997 0.067 uiso 1 1 calc r . . h1c h 1.0991 -0.0776 0.2890 0.067 uiso 1 1 calc r . . c2 c 0.95187(14) -0.05884(15) 0.33878(14) 0.0342(5) uani 1 1 d . . . c3 c 0.92556(14) 0.01652(14) 0.39663(14) 0.0329(5) uani 1 1 d . . . c4 c 0.84300(14) 0.01588(15) 0.46771(14) 0.0366(5) uani 1 1 d . . . c5 c 0.78967(16) -0.06928(15) 0.47507(16) 0.0436(6) uani 1 1 d . . . h5 h 0.7325 -0.0742 0.5200 0.052 uiso 1 1 calc r . . c6 c 0.81869(15) -0.14408(16) 0.41914(15) 0.0429(5) uani 1 1 d . . . h6 h 0.7821 -0.2008 0.4270 0.051 uiso 1 1 calc r . . c7 c 0.92340(15) -0.22328(14) 0.29401(14) 0.0360(5) uani 1 1 d . . . c8 c 0.85419(16) -0.25675(16) 0.22150(15) 0.0433(5) uani 1 1 d . . . h8 h 0.7905 -0.2256 0.2100 0.052 uiso 1 1 calc r . . c9 c 0.87767(17) -0.33546(16) 0.16585(15) 0.0465(6) uani 1 1 d . . . h9 h 0.8296 -0.3584 0.1164 0.056 uiso 1 1 calc r . . c10 c 0.97038(16) -0.38159(16) 0.18106(15) 0.0418(5) uani 1 1 d . . . c11 c 1.03934(15) -0.34722(15) 0.25492(14) 0.0380(5) uani 1 1 d . . . h11 h 1.1032 -0.3781 0.2666 0.046 uiso 1 1 calc r . . c12 c 1.01540(15) -0.26885(14) 0.31093(14) 0.0362(5) uani 1 1 d . . . h12 h 1.0625 -0.2462 0.3614 0.043 uiso 1 1 calc r . . c13 c 0.86815(15) -0.08586(16) -0.01987(17) 0.0471(6) uani 1 1 d . . . h13a h 0.8898 -0.1511 -0.0216 0.071 uiso 1 1 calc r . . h13b h 0.9143 -0.0508 0.0260 0.071 uiso 1 1 calc r . . h13c h 0.8712 -0.0596 -0.0895 0.071 uiso 1 1 calc r . . c14 c 0.76038(14) -0.07971(14) 0.01890(13) 0.0330(5) uani 1 1 d . . . c15 c 0.69648(14) -0.15509(14) 0.02047(13) 0.0328(5) uani 1 1 d . . . c16 c 0.59640(14) -0.15203(15) 0.06532(14) 0.0346(5) uani 1 1 d . . . c17 c 0.56610(15) -0.06406(15) 0.10213(16) 0.0419(5) uani 1 1 d . . . h17 h 0.4996 -0.0569 0.1314 0.050 uiso 1 1 calc r . . c18 c 0.62952(15) 0.01024(16) 0.09678(15) 0.0419(5) uani 1 1 d . . . h18 h 0.6064 0.0685 0.1222 0.050 uiso 1 1 calc r . . c19 c 0.79175(14) 0.08487(14) 0.06086(14) 0.0334(5) uani 1 1 d . . . c20 c 0.83436(15) 0.11046(15) 0.15455(15) 0.0390(5) uani 1 1 d . . . h20 h 0.8194 0.0753 0.2146 0.047 uiso 1 1 calc r . . c21 c 0.89823(14) 0.18649(15) 0.16120(14) 0.0390(5) uani 1 1 d . . . h21 h 0.9265 0.2041 0.2261 0.047 uiso 1 1 calc r . . c22 c 0.92186(14) 0.23811(15) 0.07350(15) 0.0352(5) uani 1 1 d . . . c23 c 0.87874(15) 0.21078(15) -0.02054(14) 0.0372(5) uani 1 1 d . . . h23 h 0.8944 0.2449 -0.0812 0.045 uiso 1 1 calc r . . c24 c 0.81382(15) 0.13512(15) -0.02679(14) 0.0367(5) uani 1 1 d . . . h24 h 0.7844 0.1176 -0.0912 0.044 uiso 1 1 calc r . . c26 c 0.67439(16) 0.28514(16) -0.22099(16) 0.0498(6) uani 1 1 d . . . h26a h 0.6299 0.3397 -0.2298 0.075 uiso 1 1 calc r . . h26b h 0.7185 0.2783 -0.2815 0.075 uiso 1 1 calc r . . h26c h 0.7175 0.2931 -0.1593 0.075 uiso 1 1 calc r . . n1 n 0.89829(12) -0.14065(12) 0.35216(11) 0.0363(4) uani 1 1 d . . . n2 n 0.9974(2) -0.45674(16) 0.12027(17) 0.0572(6) uani 1 1 d . . . n3 n 0.72518(11) 0.00407(12) 0.05625(11) 0.0342(4) uani 1 1 d . . . n4 n 0.98347(15) 0.31506(14) 0.08118(16) 0.0483(5) uani 1 1 d . . . o1 o 0.82082(10) 0.08917(10) 0.51917(10) 0.0434(4) uani 1 1 d . . . o2 o 0.98094(10) 0.09572(11) 0.38305(10) 0.0400(4) uani 1 1 d . . . o3 o 0.54121(10) -0.22541(10) 0.06990(10) 0.0403(4) uani 1 1 d . . . o4 o 0.73273(11) -0.23538(11) -0.02010(11) 0.0415(4) uani 1 1 d . . . o5 o 0.61277(11) 0.20490(11) -0.21007(12) 0.0496(4) uani 1 1 d . . . o6 o 0.68769(14) 0.05045(14) -0.31518(16) 0.0659(5) uani 1 1 d . . . h2a h 0.949(2) -0.4896(19) 0.098(2) 0.081(10) uiso 1 1 d . . . h2b h 1.056(2) -0.495(2) 0.141(2) 0.094(11) uiso 1 1 d . . . h2o h 0.9500(18) 0.1440(18) 0.421(2) 0.078(9) uiso 1 1 d . . . h4a h 1.0032(18) 0.3439(16) 0.0250(18) 0.058(7) uiso 1 1 d . . . h4b h 1.0232(16) 0.3211(15) 0.1396(18) 0.053(7) uiso 1 1 d . . . h4o h 0.6924(18) -0.2849(16) -0.0061(17) 0.057(7) uiso 1 1 d . . . h5o h 0.5658(19) 0.2141(17) -0.1623(19) 0.070(8) uiso 1 1 d . . . h6a h 0.668(2) 0.106(2) -0.275(3) 0.114(12) uiso 1 1 d . . . h6b h 0.728(2) 0.069(2) -0.361(2) 0.098(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 c1 0.0416(12) 0.0567(15) 0.0348(11) -0.0008(10) 0.0121(10) -0.0093(11) c2 0.0262(10) 0.0509(14) 0.0254(9) 0.0056(9) 0.0006(8) -0.0028(10) c3 0.0263(10) 0.0465(14) 0.0259(10) 0.0102(9) 0.0002(8) -0.0008(10) c4 0.0287(11) 0.0523(15) 0.0288(10) 0.0108(10) 0.0012(9) 0.0059(10) c5 0.0329(11) 0.0547(15) 0.0434(12) 0.0103(11) 0.0143(10) 0.0014(11) c6 0.0336(11) 0.0524(15) 0.0427(12) 0.0080(11) 0.0096(10) -0.0051(10) c7 0.0326(11) 0.0483(13) 0.0272(10) 0.0036(9) 0.0017(9) -0.0048(10) c8 0.0317(11) 0.0624(16) 0.0359(11) 0.0047(11) -0.0033(9) -0.0056(11) c9 0.0419(13) 0.0649(16) 0.0325(11) -0.0013(11) -0.0049(10) -0.0126(12) c10 0.0426(13) 0.0528(15) 0.0300(10) 0.0000(10) 0.0071(10) -0.0120(11) c11 0.0333(11) 0.0488(14) 0.0320(10) 0.0061(10) 0.0032(9) -0.0039(10) c12 0.0310(11) 0.0505(14) 0.0271(10) 0.0030(9) -0.0009(8) -0.0073(10) c13 0.0307(11) 0.0539(15) 0.0568(14) -0.0063(11) 0.0110(10) -0.0005(10) c14 0.0253(10) 0.0476(14) 0.0260(9) -0.0006(9) 0.0023(8) 0.0038(10) c15 0.0278(10) 0.0472(14) 0.0235(9) -0.0015(9) 0.0017(8) 0.0043(10) c16 0.0253(10) 0.0528(14) 0.0257(9) 0.0055(9) 0.0018(8) -0.0002(10) c17 0.0274(11) 0.0536(15) 0.0450(12) 0.0005(10) 0.0144(9) 0.0055(11) c18 0.0315(11) 0.0525(15) 0.0418(12) -0.0007(10) 0.0090(9) 0.0076(11) c19 0.0250(10) 0.0429(13) 0.0323(10) 0.0013(9) 0.0041(8) 0.0028(9) c20 0.0318(11) 0.0562(15) 0.0292(10) 0.0070(10) 0.0014(9) 0.0032(11) c21 0.0293(11) 0.0577(15) 0.0298(10) 0.0006(10) -0.0031(9) 0.0009(11) c22 0.0235(10) 0.0454(13) 0.0369(11) 0.0017(9) 0.0035(8) 0.0046(10) c23 0.0340(11) 0.0484(14) 0.0293(10) 0.0048(9) 0.0030(9) 0.0018(10) c24 0.0322(11) 0.0493(14) 0.0286(10) -0.0009(9) 0.0017(8) 0.0026(10) c26 0.0397(13) 0.0649(17) 0.0450(12) 0.0028(11) 0.0104(10) 0.0046(12) n1 0.0307(9) 0.0475(11) 0.0307(8) 0.0036(8) 0.0035(7) -0.0041(8) n2 0.0615(15) 0.0621(15) 0.0482(12) -0.0144(11) 0.0083(11) -0.0099(14) n3 0.0272(9) 0.0449(11) 0.0304(8) 0.0025(8) 0.0047(7) 0.0021(8) n4 0.0456(12) 0.0606(14) 0.0387(11) 0.0046(10) -0.0020(10) -0.0126(10) o1 0.0420(8) 0.0507(10) 0.0377(8) 0.0090(7) 0.0137(7) 0.0098(7) o2 0.0375(8) 0.0465(10) 0.0361(8) 0.0037(7) 0.0106(6) -0.0012(7) o3 0.0309(8) 0.0512(10) 0.0389(8) 0.0030(7) 0.0090(6) -0.0031(7) o4 0.0320(8) 0.0478(10) 0.0448(8) -0.0066(7) 0.0113(7) -0.0029(7) o5 0.0373(8) 0.0664(11) 0.0454(9) -0.0100(8) 0.0162(7) -0.0077(8) o6 0.0580(11) 0.0673(13) 0.0728(12) 0.0063(10) 0.0318(10) 0.0024(10) _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 c1 c2 1.490(3) . ? c1 h1a 0.9800 . ? c1 h1b 0.9800 . ? c1 h1c 0.9800 . ? c2 c3 1.363(3) . ? c2 n1 1.378(2) . ? c3 o2 1.358(2) . ? c3 c4 1.419(3) . ? c4 o1 1.281(2) . ? c4 c5 1.410(3) . ? c5 c6 1.353(3) . ? c5 h5 0.9500 . ? c6 n1 1.355(2) . ? c6 h6 0.9500 . ? c7 c12 1.377(3) . ? c7 c8 1.382(3) . ? c7 n1 1.446(3) . ? c8 c9 1.378(3) . ? c8 h8 0.9500 . ? c9 c10 1.386(3) . ? c9 h9 0.9500 . ? c10 n2 1.385(3) . ? c10 c11 1.396(3) . ? c11 c12 1.378(3) . ? c11 h11 0.9500 . ? c12 h12 0.9500 . ? c13 c14 1.491(3) . ? c13 h13a 0.9800 . ? c13 h13b 0.9800 . ? c13 h13c 0.9800 . ? c14 c15 1.364(3) . ? c14 n3 1.378(2) . ? c15 o4 1.354(2) . ? c15 c16 1.427(3) . ? c16 o3 1.276(2) . ? c16 c17 1.409(3) . ? c17 c18 1.350(3) . ? c17 h17 0.9500 . ? c18 n3 1.354(2) . ? c18 h18 0.9500 . ? c19 c24 1.380(3) . ? c19 c20 1.382(3) . ? c19 n3 1.448(2) . ? c20 c21 1.374(3) . ? c20 h20 0.9500 . ? c21 c22 1.395(3) . ? c21 h21 0.9500 . ? c22 n4 1.368(3) . ? c22 c23 1.395(3) . ? c23 c24 1.378(3) . ? c23 h23 0.9500 . ? c24 h24 0.9500 . ? c26 o5 1.411(3) . ? c26 h26a 0.9800 . ? c26 h26b 0.9800 . ? c26 h26c 0.9800 . ? n2 h2a 0.84(3) . ? n2 h2b 0.97(3) . ? n4 h4a 0.88(2) . ? n4 h4b 0.92(2) . ? o2 h2o 0.94(3) . ? o4 h4o 0.90(2) . ? o5 h5o 0.88(3) . ? o6 h6a 0.98(3) . ? o6 h6b 0.84(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 c2 c1 h1a 109.5 . . ? c2 c1 h1b 109.5 . . ? h1a c1 h1b 109.5 . . ? c2 c1 h1c 109.5 . . ? h1a c1 h1c 109.5 . . ? h1b c1 h1c 109.5 . . ? c3 c2 n1 118.73(17) . . ? c3 c2 c1 121.54(18) . . ? n1 c2 c1 119.70(18) . . ? o2 c3 c2 117.40(17) . . ? o2 c3 c4 119.48(18) . . ? c2 c3 c4 123.12(19) . . ? o1 c4 c5 124.52(18) . . ? o1 c4 c3 120.47(19) . . ? c5 c4 c3 115.00(19) . . ? c6 c5 c4 121.04(19) . . ? c6 c5 h5 119.5 . . ? c4 c5 h5 119.5 . . ? c5 c6 n1 122.1(2) . . ? c5 c6 h6 118.9 . . ? n1 c6 h6 118.9 . . ? c12 c7 c8 120.0(2) . . ? c12 c7 n1 120.39(17) . . ? c8 c7 n1 119.61(18) . . ? c9 c8 c7 119.9(2) . . ? c9 c8 h8 120.1 . . ? c7 c8 h8 120.1 . . ? c8 c9 c10 120.89(19) . . ? c8 c9 h9 119.6 . . ? c10 c9 h9 119.6 . . ? n2 c10 c9 121.0(2) . . ? n2 c10 c11 120.2(2) . . ? c9 c10 c11 118.6(2) . . ? c12 c11 c10 120.41(19) . . ? c12 c11 h11 119.8 . . ? c10 c11 h11 119.8 . . ? c7 c12 c11 120.22(19) . . ? c7 c12 h12 119.9 . . ? c11 c12 h12 119.9 . . ? c14 c13 h13a 109.5 . . ? c14 c13 h13b 109.5 . . ? h13a c13 h13b 109.5 . . ? c14 c13 h13c 109.5 . . ? h13a c13 h13c 109.5 . . ? h13b c13 h13c 109.5 . . ? c15 c14 n3 119.11(17) . . ? c15 c14 c13 121.90(18) . . ? n3 c14 c13 118.97(18) . . ? o4 c15 c14 117.30(17) . . ? o4 c15 c16 120.28(18) . . ? c14 c15 c16 122.39(19) . . ? o3 c16 c17 124.63(17) . . ? o3 c16 c15 120.36(19) . . ? c17 c16 c15 115.01(18) . . ? c18 c17 c16 121.42(18) . . ? c18 c17 h17 119.3 . . ? c16 c17 h17 119.3 . . ? c17 c18 n3 121.9(2) . . ? c17 c18 h18 119.1 . . ? n3 c18 h18 119.1 . . ? c24 c19 c20 120.15(19) . . ? c24 c19 n3 120.89(17) . . ? c20 c19 n3 118.95(17) . . ? c21 c20 c19 120.26(18) . . ? c21 c20 h20 119.9 . . ? c19 c20 h20 119.9 . . ? c20 c21 c22 120.55(18) . . ? c20 c21 h21 119.7 . . ? c22 c21 h21 119.7 . . ? n4 c22 c23 121.43(19) . . ? n4 c22 c21 120.18(19) . . ? c23 c22 c21 118.36(19) . . ? c24 c23 c22 120.97(18) . . ? c24 c23 h23 119.5 . . ? c22 c23 h23 119.5 . . ? c23 c24 c19 119.71(18) . . ? c23 c24 h24 120.1 . . ? c19 c24 h24 120.1 . . ? o5 c26 h26a 109.5 . . ? o5 c26 h26b 109.5 . . ? h26a c26 h26b 109.5 . . ? o5 c26 h26c 109.5 . . ? h26a c26 h26c 109.5 . . ? h26b c26 h26c 109.5 . . ? c6 n1 c2 119.94(18) . . ? c6 n1 c7 118.72(17) . . ? c2 n1 c7 121.32(15) . . ? c10 n2 h2a 116.2(19) . . ? c10 n2 h2b 118.7(17) . . ? h2a n2 h2b 111(3) . . ? c18 n3 c14 120.07(17) . . ? c18 n3 c19 118.61(17) . . ? c14 n3 c19 121.13(15) . . ? c22 n4 h4a 119.7(15) . . ? c22 n4 h4b 117.4(13) . . ? h4a n4 h4b 118(2) . . ? c3 o2 h2o 108.9(15) . . ? c15 o4 h4o 112.9(14) . . ? c26 o5 h5o 110.0(16) . . ? h6a o6 h6b 107(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag n1 c2 c3 o2 178.86(15) . . . . ? c1 c2 c3 o2 -3.1(3) . . . . ? n1 c2 c3 c4 -2.3(3) . . . . ? c1 c2 c3 c4 175.80(17) . . . . ? o2 c3 c4 o1 -0.3(3) . . . . ? c2 c3 c4 o1 -179.10(17) . . . . ? o2 c3 c4 c5 179.22(17) . . . . ? c2 c3 c4 c5 0.4(3) . . . . ? o1 c4 c5 c6 -179.07(19) . . . . ? c3 c4 c5 c6 1.5(3) . . . . ? c4 c5 c6 n1 -1.4(3) . . . . ? c12 c7 c8 c9 -0.3(3) . . . . ? n1 c7 c8 c9 180.00(18) . . . . ? c7 c8 c9 c10 -0.4(3) . . . . ? c8 c9 c10 n2 -175.4(2) . . . . ? c8 c9 c10 c11 0.7(3) . . . . ? n2 c10 c11 c12 175.81(19) . . . . ? c9 c10 c11 c12 -0.3(3) . . . . ? c8 c7 c12 c11 0.8(3) . . . . ? n1 c7 c12 c11 -179.59(17) . . . . ? c10 c11 c12 c7 -0.5(3) . . . . ? n3 c14 c15 o4 177.84(15) . . . . ? c13 c14 c15 o4 -3.6(3) . . . . ? n3 c14 c15 c16 -4.0(3) . . . . ? c13 c14 c15 c16 174.57(18) . . . . ? o4 c15 c16 o3 1.7(3) . . . . ? c14 c15 c16 o3 -176.37(17) . . . . ? o4 c15 c16 c17 -178.19(17) . . . . ? c14 c15 c16 c17 3.7(3) . . . . ? o3 c16 c17 c18 178.51(19) . . . . ? c15 c16 c17 c18 -1.6(3) . . . . ? c16 c17 c18 n3 -0.2(3) . . . . ? c24 c19 c20 c21 0.5(3) . . . . ? n3 c19 c20 c21 179.66(17) . . . . ? c19 c20 c21 c22 -0.8(3) . . . . ? c20 c21 c22 n4 178.39(19) . . . . ? c20 c21 c22 c23 0.3(3) . . . . ? n4 c22 c23 c24 -177.64(19) . . . . ? c21 c22 c23 c24 0.4(3) . . . . ? c22 c23 c24 c19 -0.7(3) . . . . ? c20 c19 c24 c23 0.2(3) . . . . ? n3 c19 c24 c23 -178.93(17) . . . . ? c5 c6 n1 c2 -0.6(3) . . . . ? c5 c6 n1 c7 -179.01(19) . . . . ? c3 c2 n1 c6 2.4(3) . . . . ? c1 c2 n1 c6 -175.75(18) . . . . ? c3 c2 n1 c7 -179.24(17) . . . . ? c1 c2 n1 c7 2.6(3) . . . . ? c12 c7 n1 c6 -113.4(2) . . . . ? c8 c7 n1 c6 66.3(2) . . . . ? c12 c7 n1 c2 68.2(2) . . . . ? c8 c7 n1 c2 -112.1(2) . . . . ? c17 c18 n3 c14 0.0(3) . . . . ? c17 c18 n3 c19 -175.01(18) . . . . ? c15 c14 n3 c18 2.0(3) . . . . ? c13 c14 n3 c18 -176.58(17) . . . . ? c15 c14 n3 c19 176.95(16) . . . . ? c13 c14 n3 c19 -1.7(3) . . . . ? c24 c19 n3 c18 -108.3(2) . . . . ? c20 c19 n3 c18 72.6(2) . . . . ? c24 c19 n3 c14 76.7(2) . . . . ? c20 c19 n3 c14 -102.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.47 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.165 _refine_diff_density_min -0.237 _refine_diff_density_rms 0.041 # Attachment '- co337-CuL1-new4pub.cif' data_co337new _database_code_depnum_ccdc_archive 'CCDC 798380' #TrackingRef '- co337-CuL1-new4pub.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Cudapp2 _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H32 Cl6 Cu N4 O4' _chemical_formula_weight 788.84 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' 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 'P 21/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 12.9970(12) _cell_length_b 15.3280(17) _cell_length_c 9.0063(8) _cell_angle_alpha 90.00 _cell_angle_beta 110.181(4) _cell_angle_gamma 90.00 _cell_volume 1684.1(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4472 _cell_measurement_theta_min 2.66 _cell_measurement_theta_max 26.39 _exptl_crystal_description blade _exptl_crystal_colour green _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.556 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 806 _exptl_absorpt_coefficient_mu 1.166 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.711 _exptl_absorpt_correction_T_max 0.890 _exptl_absorpt_process_details 'SADABS (Bruker Nonius, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 X8 APEX II' _diffrn_measurement_method 'area detector' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17157 _diffrn_reflns_av_R_equivalents 0.0345 _diffrn_reflns_av_sigmaI/netI 0.0366 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 28.27 _reflns_number_total 4105 _reflns_number_gt 2920 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0396P)^2^+1.1521P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4105 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0682 _refine_ls_R_factor_gt 0.0380 _refine_ls_wR_factor_ref 0.1000 _refine_ls_wR_factor_gt 0.0854 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 C10 C 0.68014(19) 0.86076(16) -0.0368(3) 0.0324(5) Uani 1 1 d . . . C11 C 0.63195(19) 0.86325(18) 0.0806(3) 0.0380(6) Uani 1 1 d . . . H11 H 0.5546 0.8589 0.0512 0.046 Uiso 1 1 calc R . . C12 C 0.6949(2) 0.87195(18) 0.2376(3) 0.0387(6) Uani 1 1 d . . . H12 H 0.6609 0.8727 0.3155 0.046 Uiso 1 1 calc R . . C7 C 0.80739(19) 0.87969(16) 0.2827(3) 0.0315(5) Uani 1 1 d . . . C8 C 0.85666(19) 0.87796(16) 0.1706(3) 0.0327(5) Uani 1 1 d . . . H8 H 0.9340 0.8834 0.2015 0.039 Uiso 1 1 calc R . . C9 C 0.79430(19) 0.86832(16) 0.0130(3) 0.0330(5) Uani 1 1 d . . . H9 H 0.8296 0.8668 -0.0635 0.040 Uiso 1 1 calc R . . C13 C 0.6691(2) 0.8603(2) -0.3120(3) 0.0485(7) Uani 1 1 d . . . H13A H 0.6992 0.9194 -0.3059 0.073 Uiso 1 1 calc R . . H13B H 0.6142 0.8509 -0.4172 0.073 Uiso 1 1 calc R . . H13C H 0.7283 0.8176 -0.2934 0.073 Uiso 1 1 calc R . . C14 C 0.5013(2) 0.8522(3) -0.2424(3) 0.0784(13) Uani 1 1 d . . . H14A H 0.4767 0.8122 -0.1766 0.118 Uiso 1 1 calc R . . H14B H 0.4699 0.8343 -0.3534 0.118 Uiso 1 1 calc R . . H14C H 0.4771 0.9116 -0.2308 0.118 Uiso 1 1 calc R . . C6 C 0.94220(19) 0.82157(17) 0.5168(3) 0.0339(5) Uani 1 1 d . . . H6 H 0.9499 0.7743 0.4532 0.041 Uiso 1 1 calc R . . C5 C 1.00080(19) 0.82103(16) 0.6743(3) 0.0343(5) Uani 1 1 d . . . H5 H 1.0501 0.7745 0.7192 0.041 Uiso 1 1 calc R . . C4 C 0.98845(17) 0.88860(16) 0.7696(2) 0.0288(5) Uani 1 1 d . . . C3 C 0.91706(17) 0.95913(15) 0.6956(2) 0.0268(5) Uani 1 1 d . . . C2 C 0.86220(17) 0.95832(16) 0.5348(2) 0.0287(5) Uani 1 1 d . . . C1 C 0.7941(2) 1.03472(18) 0.4543(3) 0.0397(6) Uani 1 1 d . . . H1A H 0.8062 1.0466 0.3547 0.059 Uiso 1 1 calc R . . H1B H 0.8150 1.0860 0.5231 0.059 Uiso 1 1 calc R . . H1C H 0.7164 1.0216 0.4324 0.059 Uiso 1 1 calc R . . C15 C 0.7165(2) 1.12680(19) -0.1423(3) 0.0434(6) Uani 1 1 d . A 1 H15 H 0.7796 1.0927 -0.1516 0.052 Uiso 1 1 calc R A 1 N2 N 0.61826(17) 0.85017(17) -0.1932(2) 0.0435(6) Uani 1 1 d . . . N1 N 0.87329(15) 0.88767(13) 0.4485(2) 0.0310(4) Uani 1 1 d . . . O2 O 0.90753(12) 1.02341(10) 0.78774(17) 0.0304(4) Uani 1 1 d . . . O1 O 1.03649(13) 0.89223(11) 0.92161(18) 0.0337(4) Uani 1 1 d . . . Cl1 Cl 0.69048(15) 1.09168(9) 0.0233(2) 0.0563(4) Uani 0.68 1 d P A 1 Cl2 Cl 0.6039(2) 1.10957(17) -0.3097(2) 0.0770(7) Uani 0.68 1 d P A 1 Cl3 Cl 0.75249(11) 1.23819(10) -0.1216(2) 0.0766(5) Uani 0.68 1 d P A 1 Cl1B Cl 0.6981(4) 1.1506(6) 0.0270(5) 0.154(3) Uani 0.32 1 d P B 2 Cl2B Cl 0.5906(5) 1.0748(4) -0.2747(8) 0.0926(19) Uani 0.32 1 d P C 2 Cl3B Cl 0.7335(3) 1.2140(2) -0.2446(7) 0.0950(12) Uani 0.32 1 d P D 2 Cu1 Cu 1.0000 1.0000 1.0000 0.02917(12) Uani 1 2 d S . . 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 C10 0.0314(12) 0.0366(14) 0.0295(11) -0.0018(10) 0.0110(9) -0.0046(10) C11 0.0248(12) 0.0562(17) 0.0342(12) -0.0027(11) 0.0118(9) -0.0080(11) C12 0.0309(13) 0.0581(17) 0.0309(11) -0.0030(11) 0.0156(10) -0.0067(11) C7 0.0303(12) 0.0378(14) 0.0264(10) -0.0028(9) 0.0099(9) -0.0020(10) C8 0.0260(12) 0.0403(14) 0.0337(11) 0.0003(10) 0.0128(9) -0.0012(10) C9 0.0321(12) 0.0399(14) 0.0302(11) -0.0030(10) 0.0148(9) -0.0020(10) C13 0.0460(16) 0.070(2) 0.0304(12) -0.0012(12) 0.0137(11) -0.0117(14) C14 0.0348(16) 0.157(4) 0.0358(14) 0.0055(19) 0.0027(12) -0.029(2) C6 0.0314(13) 0.0356(14) 0.0373(12) -0.0043(10) 0.0149(10) 0.0009(10) C5 0.0295(12) 0.0349(14) 0.0384(12) 0.0021(10) 0.0116(10) 0.0058(10) C4 0.0193(11) 0.0375(13) 0.0296(10) 0.0031(9) 0.0083(8) 0.0000(9) C3 0.0212(11) 0.0322(12) 0.0284(10) 0.0022(9) 0.0103(8) 0.0004(9) C2 0.0246(11) 0.0354(13) 0.0275(10) 0.0014(9) 0.0107(9) 0.0017(9) C1 0.0441(15) 0.0416(14) 0.0273(11) 0.0037(10) 0.0048(10) 0.0085(12) C15 0.0342(14) 0.0539(18) 0.0437(14) 0.0100(12) 0.0155(11) 0.0123(12) N2 0.0318(11) 0.0683(16) 0.0300(10) -0.0019(10) 0.0100(8) -0.0112(11) N1 0.0271(10) 0.0388(12) 0.0271(9) -0.0010(8) 0.0093(7) -0.0011(8) O2 0.0266(8) 0.0367(10) 0.0255(7) 0.0005(6) 0.0059(6) 0.0071(6) O1 0.0289(8) 0.0406(10) 0.0280(7) 0.0036(7) 0.0054(6) 0.0082(7) Cl1 0.0570(8) 0.0685(8) 0.0516(7) 0.0160(7) 0.0290(6) 0.0046(7) Cl2 0.0593(12) 0.109(2) 0.0433(7) -0.0133(9) -0.0072(7) 0.0207(11) Cl3 0.0430(7) 0.0463(8) 0.1261(13) 0.0303(9) 0.0106(8) 0.0020(5) Cl1B 0.059(2) 0.349(10) 0.0495(19) -0.033(4) 0.0129(16) 0.058(5) Cl2B 0.0494(19) 0.080(3) 0.146(5) -0.022(3) 0.030(3) 0.001(2) Cl3B 0.061(2) 0.060(2) 0.177(4) 0.026(3) 0.057(3) 0.0072(16) Cu1 0.0231(2) 0.0383(2) 0.02392(17) 0.00204(17) 0.00530(13) 0.00464(17) _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 C10 N2 1.370(3) . ? C10 C9 1.399(3) . ? C10 C11 1.403(3) . ? C11 C12 1.374(3) . ? C11 H11 0.9500 . ? C12 C7 1.381(3) . ? C12 H12 0.9500 . ? C7 C8 1.370(3) . ? C7 N1 1.448(3) . ? C8 C9 1.378(3) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C13 N2 1.446(3) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 N2 1.430(4) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C6 N1 1.352(3) . ? C6 C5 1.359(3) . ? C6 H6 0.9500 . ? C5 C4 1.389(3) . ? C5 H5 0.9500 . ? C4 O1 1.295(3) . ? C4 C3 1.431(3) . ? C3 O2 1.321(3) . ? C3 C2 1.376(3) . ? C2 N1 1.369(3) . ? C2 C1 1.496(3) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C15 Cl2 1.721(3) . ? C15 Cl1 1.725(3) . ? C15 Cl3 1.763(3) . ? C15 H15 1.0000 . ? O2 Cu1 1.9085(14) . ? O1 Cu1 1.9191(16) . ? Cu1 O2 1.9085(14) 3_777 ? Cu1 O1 1.9191(16) 3_777 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 C10 C9 121.4(2) . . ? N2 C10 C11 121.5(2) . . ? C9 C10 C11 117.1(2) . . ? C12 C11 C10 121.0(2) . . ? C12 C11 H11 119.5 . . ? C10 C11 H11 119.5 . . ? C11 C12 C7 120.4(2) . . ? C11 C12 H12 119.8 . . ? C7 C12 H12 119.8 . . ? C8 C7 C12 119.9(2) . . ? C8 C7 N1 120.1(2) . . ? C12 C7 N1 120.04(19) . . ? C7 C8 C9 120.2(2) . . ? C7 C8 H8 119.9 . . ? C9 C8 H8 119.9 . . ? C8 C9 C10 121.4(2) . . ? C8 C9 H9 119.3 . . ? C10 C9 H9 119.3 . . ? N2 C13 H13A 109.5 . . ? N2 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N2 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N2 C14 H14A 109.5 . . ? N2 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N2 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N1 C6 C5 121.6(2) . . ? N1 C6 H6 119.2 . . ? C5 C6 H6 119.2 . . ? C6 C5 C4 119.8(2) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? O1 C4 C5 124.6(2) . . ? O1 C4 C3 117.3(2) . . ? C5 C4 C3 118.1(2) . . ? O2 C3 C2 122.7(2) . . ? O2 C3 C4 117.21(19) . . ? C2 C3 C4 120.0(2) . . ? N1 C2 C3 119.1(2) . . ? N1 C2 C1 120.31(19) . . ? C3 C2 C1 120.5(2) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? Cl2 C15 Cl1 110.39(18) . . ? Cl2 C15 Cl3 110.83(17) . . ? Cl1 C15 Cl3 109.57(18) . . ? Cl2 C15 H15 108.7 . . ? Cl1 C15 H15 108.7 . . ? Cl3 C15 H15 108.7 . . ? C10 N2 C14 120.0(2) . . ? C10 N2 C13 119.5(2) . . ? C14 N2 C13 118.5(2) . . ? C6 N1 C2 121.15(19) . . ? C6 N1 C7 118.0(2) . . ? C2 N1 C7 120.77(19) . . ? C3 O2 Cu1 109.01(13) . . ? C4 O1 Cu1 109.61(14) . . ? O2 Cu1 O2 180.000(1) 3_777 . ? O2 Cu1 O1 86.76(6) 3_777 3_777 ? O2 Cu1 O1 93.24(6) . 3_777 ? O2 Cu1 O1 93.24(6) 3_777 . ? O2 Cu1 O1 86.76(6) . . ? O1 Cu1 O1 180.000(1) 3_777 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 C10 C11 C12 178.5(3) . . . . ? C9 C10 C11 C12 -0.6(4) . . . . ? C10 C11 C12 C7 0.9(4) . . . . ? C11 C12 C7 C8 -0.5(4) . . . . ? C11 C12 C7 N1 -179.2(2) . . . . ? C12 C7 C8 C9 -0.2(4) . . . . ? N1 C7 C8 C9 178.5(2) . . . . ? C7 C8 C9 C10 0.5(4) . . . . ? N2 C10 C9 C8 -179.2(2) . . . . ? C11 C10 C9 C8 -0.1(4) . . . . ? N1 C6 C5 C4 1.6(4) . . . . ? C6 C5 C4 O1 176.7(2) . . . . ? C6 C5 C4 C3 -2.8(3) . . . . ? O1 C4 C3 O2 1.4(3) . . . . ? C5 C4 C3 O2 -179.06(19) . . . . ? O1 C4 C3 C2 -178.9(2) . . . . ? C5 C4 C3 C2 0.6(3) . . . . ? O2 C3 C2 N1 -177.55(19) . . . . ? C4 C3 C2 N1 2.8(3) . . . . ? O2 C3 C2 C1 4.3(3) . . . . ? C4 C3 C2 C1 -175.3(2) . . . . ? C9 C10 N2 C14 -173.2(3) . . . . ? C11 C10 N2 C14 7.8(4) . . . . ? C9 C10 N2 C13 -9.7(4) . . . . ? C11 C10 N2 C13 171.3(3) . . . . ? C5 C6 N1 C2 2.0(3) . . . . ? C5 C6 N1 C7 -175.0(2) . . . . ? C3 C2 N1 C6 -4.2(3) . . . . ? C1 C2 N1 C6 174.0(2) . . . . ? C3 C2 N1 C7 172.8(2) . . . . ? C1 C2 N1 C7 -9.1(3) . . . . ? C8 C7 N1 C6 -65.3(3) . . . . ? C12 C7 N1 C6 113.3(3) . . . . ? C8 C7 N1 C2 117.6(3) . . . . ? C12 C7 N1 C2 -63.7(3) . . . . ? C2 C3 O2 Cu1 -178.43(17) . . . . ? C4 C3 O2 Cu1 1.2(2) . . . . ? C5 C4 O1 Cu1 177.28(18) . . . . ? C3 C4 O1 Cu1 -3.2(2) . . . . ? C3 O2 Cu1 O2 -162(100) . . . 3_777 ? C3 O2 Cu1 O1 177.66(14) . . . 3_777 ? C3 O2 Cu1 O1 -2.34(14) . . . . ? C4 O1 Cu1 O2 -176.90(15) . . . 3_777 ? C4 O1 Cu1 O2 3.10(15) . . . . ? C4 O1 Cu1 O1 -59(100) . . . 3_777 ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 28.27 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.434 _refine_diff_density_min -0.326 _refine_diff_density_rms 0.060 # Attachment '- co338-HL4-new4pub.cif' data_co338 _database_code_depnum_ccdc_archive 'CCDC 798381' #TrackingRef '- co338-HL4-new4pub.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Hbt6p _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H14 N2 O3 S' _chemical_formula_weight 290.33 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' S S 0.1246 0.1234 '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 11.368(2) _cell_length_b 11.457(2) _cell_length_c 12.809(2) _cell_angle_alpha 67.679(10) _cell_angle_beta 76.787(11) _cell_angle_gamma 74.165(11) _cell_volume 1470.0(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 8087 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 27.45 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.312 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.228 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.808 _exptl_absorpt_correction_T_max 0.984 _exptl_absorpt_process_details 'SADABS (Bruker Nonius, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 X8 APEX II' _diffrn_measurement_method 'area detector' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26697 _diffrn_reflns_av_R_equivalents 0.0364 _diffrn_reflns_av_sigmaI/netI 0.0390 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 27.72 _reflns_number_total 6723 _reflns_number_gt 5076 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0397P)^2^+0.3393P] 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 6723 _refine_ls_number_parameters 381 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0581 _refine_ls_R_factor_gt 0.0386 _refine_ls_wR_factor_ref 0.0947 _refine_ls_wR_factor_gt 0.0864 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _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 C1 C 0.36662(17) 0.92760(16) 0.09270(14) 0.0342(4) Uani 1 1 d . . . H1A H 0.3888 0.9085 0.0215 0.051 Uiso 1 1 calc R . . H1B H 0.3176 0.8669 0.1488 0.051 Uiso 1 1 calc R . . H1C H 0.4419 0.9192 0.1222 0.051 Uiso 1 1 calc R . . C2 C 0.29109(14) 1.06508(15) 0.07029(12) 0.0231(3) Uani 1 1 d . . . C3 C 0.26965(14) 1.14880(15) -0.03929(12) 0.0239(3) Uani 1 1 d . . . C4 C 0.19258(13) 1.27818(15) -0.06052(12) 0.0239(3) Uani 1 1 d . . . C5 C 0.13916(14) 1.31299(16) 0.03987(13) 0.0282(4) Uani 1 1 d . . . H5 H 0.0864 1.3951 0.0322 0.034 Uiso 1 1 calc R . . C6 C 0.16344(14) 1.22889(15) 0.14734(13) 0.0266(3) Uani 1 1 d . . . H6 H 0.1281 1.2553 0.2116 0.032 Uiso 1 1 calc R . . C7 C 0.25677(14) 1.02038(14) 0.28059(12) 0.0226(3) Uani 1 1 d . . . C8 C 0.37390(14) 0.99272(15) 0.31734(13) 0.0260(3) Uani 1 1 d . . . H8 H 0.4391 1.0309 0.2667 0.031 Uiso 1 1 calc R . . C9 C 0.39319(15) 0.90905(15) 0.42835(13) 0.0274(3) Uani 1 1 d . . . H9 H 0.4706 0.8914 0.4536 0.033 Uiso 1 1 calc R . . C10 C 0.29529(14) 0.85148(15) 0.50201(12) 0.0247(3) Uani 1 1 d . . . C11 C 0.19931(17) 0.71958(17) 0.65426(14) 0.0357(4) Uani 1 1 d . . . H11 H 0.1879 0.6567 0.7278 0.043 Uiso 1 1 calc R . . C12 C 0.17917(14) 0.88054(15) 0.46237(13) 0.0246(3) Uani 1 1 d . . . C13 C 0.15786(14) 0.96628(15) 0.35098(12) 0.0249(3) Uani 1 1 d . . . H13 H 0.0802 0.9858 0.3257 0.030 Uiso 1 1 calc R . . C14 C 0.37418(17) 0.59465(16) 1.40380(14) 0.0321(4) Uani 1 1 d . . . H14A H 0.3576 0.6131 1.4751 0.048 Uiso 1 1 calc R . . H14B H 0.3202 0.6601 1.3502 0.048 Uiso 1 1 calc R . . H14C H 0.4607 0.5962 1.3705 0.048 Uiso 1 1 calc R . . C15 C 0.34952(13) 0.46189(15) 1.42797(12) 0.0221(3) Uani 1 1 d . . . C16 C 0.31556(13) 0.38224(15) 1.53836(12) 0.0225(3) Uani 1 1 d . . . C17 C 0.28315(13) 0.25909(15) 1.56130(12) 0.0227(3) Uani 1 1 d . . . C18 C 0.29028(14) 0.22458(15) 1.46203(13) 0.0257(3) Uani 1 1 d . . . H18 H 0.2686 0.1464 1.4714 0.031 Uiso 1 1 calc R . . C19 C 0.32805(14) 0.30342(15) 1.35402(13) 0.0251(3) Uani 1 1 d . . . H19 H 0.3342 0.2772 1.2906 0.030 Uiso 1 1 calc R . . C20 C 0.38930(14) 0.50361(15) 1.21815(12) 0.0225(3) Uani 1 1 d . . . C21 C 0.51305(14) 0.52068(15) 1.18033(13) 0.0255(3) Uani 1 1 d . . . H21 H 0.5741 0.4774 1.2298 0.031 Uiso 1 1 calc R . . C22 C 0.54395(14) 0.60240(15) 1.06901(13) 0.0265(3) Uani 1 1 d . . . H22 H 0.6265 0.6141 1.0423 0.032 Uiso 1 1 calc R . . C23 C 0.45153(14) 0.66765(15) 0.99630(12) 0.0246(3) Uani 1 1 d . . . C24 C 0.36338(18) 0.80214(18) 0.84174(14) 0.0373(4) Uani 1 1 d . . . H24 H 0.3579 0.8634 0.7672 0.045 Uiso 1 1 calc R . . C25 C 0.32862(15) 0.64755(15) 1.03595(12) 0.0254(3) Uani 1 1 d . . . C26 C 0.29593(14) 0.56390(15) 1.14775(12) 0.0259(3) Uani 1 1 d . . . H26 H 0.2143 0.5492 1.1740 0.031 Uiso 1 1 calc R . . C27 C -0.01601(16) 1.49107(19) -0.35603(15) 0.0381(4) Uani 1 1 d . . . H27A H -0.0874 1.5398 -0.3962 0.057 Uiso 1 1 calc R . . H27B H -0.0158 1.3987 -0.3291 0.057 Uiso 1 1 calc R . . H27C H 0.0601 1.5079 -0.4081 0.057 Uiso 1 1 calc R . . C28 C 0.0216(2) 0.0596(3) 1.8392(2) 0.0705(7) Uani 1 1 d . . . H28A H 0.0771 0.0591 1.8878 0.106 Uiso 1 1 calc R . . H28B H -0.0348 0.0014 1.8844 0.106 Uiso 1 1 calc R . . H28C H -0.0263 0.1472 1.8081 0.106 Uiso 1 1 calc R . . N1 N 0.23775(11) 1.10757(12) 0.16346(10) 0.0228(3) Uani 1 1 d . . . N2 N 0.30359(14) 0.75964(14) 0.61362(11) 0.0325(3) Uani 1 1 d . . . N3 N 0.35718(11) 0.41976(12) 1.33613(10) 0.0224(3) Uani 1 1 d . . . N4 N 0.46851(14) 0.75693(13) 0.88403(11) 0.0310(3) Uani 1 1 d . . . O1 O 0.17644(10) 1.35504(11) -0.16346(9) 0.0335(3) Uani 1 1 d . . . O2 O 0.32519(11) 1.10557(12) -0.12928(9) 0.0349(3) Uani 1 1 d . . . H2 H 0.2921 1.1537 -0.1876 0.052 Uiso 1 1 calc R . . O3 O 0.25147(11) 0.18706(11) 1.66465(9) 0.0317(3) Uani 1 1 d . . . O4 O 0.31084(11) 0.42414(11) 1.62769(9) 0.0318(3) Uani 1 1 d . . . H4 H 0.2747 0.3776 1.6875 0.048 Uiso 1 1 calc R . . O5 O -0.02341(11) 1.53068(13) -0.25961(10) 0.0355(3) Uani 1 1 d . . . O6 O 0.09273(13) 0.01721(16) 1.74758(12) 0.0529(4) Uani 1 1 d . . . S1 S 0.08054(4) 0.78687(4) 0.56705(3) 0.03531(12) Uani 1 1 d . . . S2 S 0.23340(4) 0.74382(5) 0.92970(4) 0.03978(13) Uani 1 1 d . . . H5O H 0.035(2) 1.478(2) -0.2205(19) 0.065(7) Uiso 1 1 d . . . H6O H 0.141(2) 0.076(2) 1.710(2) 0.082(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 C1 0.0469(10) 0.0270(9) 0.0262(8) -0.0115(7) -0.0068(7) 0.0010(8) C2 0.0237(7) 0.0243(8) 0.0233(7) -0.0105(6) -0.0031(6) -0.0045(6) C3 0.0241(8) 0.0273(9) 0.0212(7) -0.0099(6) -0.0031(6) -0.0046(6) C4 0.0204(7) 0.0284(9) 0.0205(7) -0.0059(6) -0.0035(6) -0.0044(6) C5 0.0270(8) 0.0256(9) 0.0247(8) -0.0076(7) -0.0020(6) 0.0032(7) C6 0.0268(8) 0.0276(9) 0.0227(8) -0.0104(7) -0.0010(6) -0.0006(7) C7 0.0281(8) 0.0202(8) 0.0185(7) -0.0069(6) -0.0042(6) -0.0022(6) C8 0.0260(8) 0.0260(9) 0.0266(8) -0.0093(7) -0.0022(6) -0.0073(7) C9 0.0269(8) 0.0278(9) 0.0304(8) -0.0115(7) -0.0109(7) -0.0022(7) C10 0.0325(8) 0.0204(8) 0.0211(7) -0.0091(6) -0.0066(6) 0.0000(7) C11 0.0480(11) 0.0333(10) 0.0192(8) -0.0045(7) -0.0036(7) -0.0050(8) C12 0.0265(8) 0.0244(8) 0.0217(7) -0.0089(6) 0.0000(6) -0.0047(6) C13 0.0246(8) 0.0263(9) 0.0225(7) -0.0079(6) -0.0040(6) -0.0034(6) C14 0.0461(10) 0.0272(9) 0.0251(8) -0.0109(7) 0.0004(7) -0.0124(8) C15 0.0227(7) 0.0226(8) 0.0211(7) -0.0093(6) -0.0020(6) -0.0030(6) C16 0.0215(7) 0.0269(9) 0.0204(7) -0.0110(6) -0.0016(6) -0.0039(6) C17 0.0207(7) 0.0254(8) 0.0195(7) -0.0057(6) -0.0023(6) -0.0039(6) C18 0.0315(8) 0.0226(8) 0.0245(8) -0.0082(6) -0.0032(6) -0.0084(7) C19 0.0313(8) 0.0248(9) 0.0216(7) -0.0109(6) -0.0024(6) -0.0062(7) C20 0.0278(8) 0.0218(8) 0.0173(7) -0.0074(6) 0.0002(6) -0.0061(6) C21 0.0243(8) 0.0272(9) 0.0257(8) -0.0105(7) -0.0038(6) -0.0037(7) C22 0.0256(8) 0.0299(9) 0.0278(8) -0.0139(7) 0.0030(6) -0.0112(7) C23 0.0327(8) 0.0238(8) 0.0201(7) -0.0108(6) 0.0031(6) -0.0110(7) C24 0.0536(11) 0.0381(11) 0.0197(8) -0.0048(7) -0.0025(8) -0.0180(9) C25 0.0306(8) 0.0280(9) 0.0188(7) -0.0080(6) -0.0039(6) -0.0073(7) C26 0.0260(8) 0.0306(9) 0.0205(7) -0.0082(6) 0.0005(6) -0.0088(7) C27 0.0303(9) 0.0471(12) 0.0352(9) -0.0154(8) -0.0052(7) -0.0026(8) C28 0.0584(14) 0.112(2) 0.0509(14) -0.0271(14) 0.0060(11) -0.0460(15) N1 0.0250(6) 0.0226(7) 0.0182(6) -0.0056(5) -0.0028(5) -0.0032(5) N2 0.0432(8) 0.0301(8) 0.0214(7) -0.0062(6) -0.0081(6) -0.0040(7) N3 0.0255(6) 0.0229(7) 0.0185(6) -0.0074(5) -0.0003(5) -0.0061(5) N4 0.0439(8) 0.0309(8) 0.0202(6) -0.0092(6) 0.0019(6) -0.0153(7) O1 0.0340(6) 0.0364(7) 0.0196(5) -0.0038(5) -0.0047(5) 0.0021(5) O2 0.0432(7) 0.0366(7) 0.0208(5) -0.0132(5) -0.0082(5) 0.0063(5) O3 0.0421(7) 0.0353(7) 0.0183(5) -0.0045(5) -0.0027(5) -0.0168(5) O4 0.0427(7) 0.0380(7) 0.0200(5) -0.0135(5) 0.0031(5) -0.0178(6) O5 0.0301(6) 0.0409(8) 0.0304(6) -0.0123(6) -0.0043(5) 0.0014(6) O6 0.0522(9) 0.0714(11) 0.0420(8) -0.0119(7) -0.0045(7) -0.0359(8) S1 0.0324(2) 0.0397(3) 0.0248(2) -0.00328(18) 0.00256(17) -0.00984(19) S2 0.0398(3) 0.0506(3) 0.0234(2) -0.00032(19) -0.01016(18) -0.0137(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.527(2) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.398(2) . ? C2 N1 1.4065(18) . ? C3 O2 1.3794(17) . ? C3 C4 1.460(2) . ? C4 O1 1.2993(18) . ? C4 C5 1.443(2) . ? C5 C6 1.386(2) . ? C5 H5 0.9500 . ? C6 N1 1.382(2) . ? C6 H6 0.9500 . ? C7 C13 1.398(2) . ? C7 C8 1.428(2) . ? C7 N1 1.4791(19) . ? C8 C9 1.408(2) . ? C8 H8 0.9500 . ? C9 C10 1.418(2) . ? C9 H9 0.9500 . ? C10 N2 1.423(2) . ? C10 C12 1.431(2) . ? C11 N2 1.312(2) . ? C11 S1 1.7699(19) . ? C11 H11 0.9500 . ? C12 C13 1.422(2) . ? C12 S1 1.7559(16) . ? C13 H13 0.9500 . ? C14 C15 1.524(2) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C16 1.394(2) . ? C15 N3 1.4092(18) . ? C16 O4 1.3848(17) . ? C16 C17 1.460(2) . ? C17 O3 1.2953(18) . ? C17 C18 1.448(2) . ? C18 C19 1.380(2) . ? C18 H18 0.9500 . ? C19 N3 1.383(2) . ? C19 H19 0.9500 . ? C20 C26 1.408(2) . ? C20 C21 1.421(2) . ? C20 N3 1.4753(18) . ? C21 C22 1.403(2) . ? C21 H21 0.9500 . ? C22 C23 1.421(2) . ? C22 H22 0.9500 . ? C23 N4 1.419(2) . ? C23 C25 1.423(2) . ? C24 N4 1.317(2) . ? C24 S2 1.7622(18) . ? C24 H24 0.9500 . ? C25 C26 1.420(2) . ? C25 S2 1.7670(16) . ? C26 H26 0.9500 . ? C27 O5 1.448(2) . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 O6 1.432(3) . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? O2 H2 0.8400 . ? O4 H4 0.8400 . ? O5 H5O 0.88(2) . ? O6 H6O 0.90(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 C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 C2 N1 118.82(14) . . ? C3 C2 C1 122.29(13) . . ? N1 C2 C1 118.86(13) . . ? O2 C3 C2 117.57(14) . . ? O2 C3 C4 119.96(13) . . ? C2 C3 C4 122.46(13) . . ? O1 C4 C5 123.67(14) . . ? O1 C4 C3 121.17(13) . . ? C5 C4 C3 115.15(13) . . ? C6 C5 C4 121.20(14) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? N1 C6 C5 121.71(14) . . ? N1 C6 H6 119.1 . . ? C5 C6 H6 119.1 . . ? C13 C7 C8 122.43(14) . . ? C13 C7 N1 117.74(13) . . ? C8 C7 N1 119.82(13) . . ? C9 C8 C7 120.23(14) . . ? C9 C8 H8 119.9 . . ? C7 C8 H8 119.9 . . ? C8 C9 C10 118.98(14) . . ? C8 C9 H9 120.5 . . ? C10 C9 H9 120.5 . . ? C9 C10 N2 125.15(14) . . ? C9 C10 C12 119.44(13) . . ? N2 C10 C12 115.34(14) . . ? N2 C11 S1 117.56(13) . . ? N2 C11 H11 121.2 . . ? S1 C11 H11 121.2 . . ? C13 C12 C10 122.18(14) . . ? C13 C12 S1 128.42(12) . . ? C10 C12 S1 109.25(11) . . ? C7 C13 C12 116.73(14) . . ? C7 C13 H13 121.6 . . ? C12 C13 H13 121.6 . . ? C15 C14 H14A 109.5 . . ? C15 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C15 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C16 C15 N3 118.81(13) . . ? C16 C15 C14 121.88(13) . . ? N3 C15 C14 119.28(13) . . ? O4 C16 C15 117.99(13) . . ? O4 C16 C17 119.92(13) . . ? C15 C16 C17 122.08(13) . . ? O3 C17 C18 123.55(14) . . ? O3 C17 C16 120.87(13) . . ? C18 C17 C16 115.57(13) . . ? C19 C18 C17 121.07(14) . . ? C19 C18 H18 119.5 . . ? C17 C18 H18 119.5 . . ? C18 C19 N3 121.40(13) . . ? C18 C19 H19 119.3 . . ? N3 C19 H19 119.3 . . ? C26 C20 C21 122.66(13) . . ? C26 C20 N3 118.64(13) . . ? C21 C20 N3 118.70(13) . . ? C22 C21 C20 119.12(14) . . ? C22 C21 H21 120.4 . . ? C20 C21 H21 120.4 . . ? C21 C22 C23 119.89(14) . . ? C21 C22 H22 120.1 . . ? C23 C22 H22 120.1 . . ? N4 C23 C22 125.85(14) . . ? N4 C23 C25 114.35(14) . . ? C22 C23 C25 119.78(13) . . ? N4 C24 S2 116.97(12) . . ? N4 C24 H24 121.5 . . ? S2 C24 H24 121.5 . . ? C26 C25 C23 121.16(14) . . ? C26 C25 S2 128.92(12) . . ? C23 C25 S2 109.89(11) . . ? C20 C26 C25 117.36(14) . . ? C20 C26 H26 121.3 . . ? C25 C26 H26 121.3 . . ? O5 C27 H27A 109.5 . . ? O5 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? O5 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? O6 C28 H28A 109.5 . . ? O6 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? O6 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C6 N1 C2 120.64(12) . . ? C6 N1 C7 119.24(12) . . ? C2 N1 C7 120.08(12) . . ? C11 N2 C10 109.09(14) . . ? C19 N3 C15 121.00(12) . . ? C19 N3 C20 118.87(12) . . ? C15 N3 C20 120.02(12) . . ? C24 N4 C23 110.26(14) . . ? C3 O2 H2 109.5 . . ? C16 O4 H4 109.5 . . ? C27 O5 H5O 106.9(15) . . ? C28 O6 H6O 103.9(17) . . ? C12 S1 C11 88.74(8) . . ? C24 S2 C25 88.53(8) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C2 C3 O2 178.68(13) . . . . ? C1 C2 C3 O2 -3.5(2) . . . . ? N1 C2 C3 C4 -0.8(2) . . . . ? C1 C2 C3 C4 176.99(14) . . . . ? O2 C3 C4 O1 -1.1(2) . . . . ? C2 C3 C4 O1 178.44(14) . . . . ? O2 C3 C4 C5 179.94(14) . . . . ? C2 C3 C4 C5 -0.6(2) . . . . ? O1 C4 C5 C6 -177.42(15) . . . . ? C3 C4 C5 C6 1.5(2) . . . . ? C4 C5 C6 N1 -1.2(2) . . . . ? C13 C7 C8 C9 -0.5(2) . . . . ? N1 C7 C8 C9 -179.50(13) . . . . ? C7 C8 C9 C10 1.0(2) . . . . ? C8 C9 C10 N2 176.17(14) . . . . ? C8 C9 C10 C12 -0.6(2) . . . . ? C9 C10 C12 C13 -0.3(2) . . . . ? N2 C10 C12 C13 -177.36(14) . . . . ? C9 C10 C12 S1 175.59(11) . . . . ? N2 C10 C12 S1 -1.46(17) . . . . ? C8 C7 C13 C12 -0.4(2) . . . . ? N1 C7 C13 C12 178.65(13) . . . . ? C10 C12 C13 C7 0.8(2) . . . . ? S1 C12 C13 C7 -174.30(12) . . . . ? N3 C15 C16 O4 178.78(12) . . . . ? C14 C15 C16 O4 -3.3(2) . . . . ? N3 C15 C16 C17 -2.4(2) . . . . ? C14 C15 C16 C17 175.47(14) . . . . ? O4 C16 C17 O3 -1.0(2) . . . . ? C15 C16 C17 O3 -179.75(14) . . . . ? O4 C16 C17 C18 179.59(13) . . . . ? C15 C16 C17 C18 0.8(2) . . . . ? O3 C17 C18 C19 -178.11(15) . . . . ? C16 C17 C18 C19 1.3(2) . . . . ? C17 C18 C19 N3 -1.8(2) . . . . ? C26 C20 C21 C22 1.1(2) . . . . ? N3 C20 C21 C22 -178.67(13) . . . . ? C20 C21 C22 C23 0.6(2) . . . . ? C21 C22 C23 N4 177.15(14) . . . . ? C21 C22 C23 C25 -1.4(2) . . . . ? N4 C23 C25 C26 -178.16(14) . . . . ? C22 C23 C25 C26 0.5(2) . . . . ? N4 C23 C25 S2 -0.32(16) . . . . ? C22 C23 C25 S2 178.37(11) . . . . ? C21 C20 C26 C25 -1.9(2) . . . . ? N3 C20 C26 C25 177.86(13) . . . . ? C23 C25 C26 C20 1.1(2) . . . . ? S2 C25 C26 C20 -176.33(12) . . . . ? C5 C6 N1 C2 -0.3(2) . . . . ? C5 C6 N1 C7 -177.88(14) . . . . ? C3 C2 N1 C6 1.3(2) . . . . ? C1 C2 N1 C6 -176.60(14) . . . . ? C3 C2 N1 C7 178.84(13) . . . . ? C1 C2 N1 C7 0.9(2) . . . . ? C13 C7 N1 C6 71.98(18) . . . . ? C8 C7 N1 C6 -108.98(16) . . . . ? C13 C7 N1 C2 -105.59(16) . . . . ? C8 C7 N1 C2 73.44(18) . . . . ? S1 C11 N2 C10 -0.90(18) . . . . ? C9 C10 N2 C11 -175.35(15) . . . . ? C12 C10 N2 C11 1.52(19) . . . . ? C18 C19 N3 C15 0.1(2) . . . . ? C18 C19 N3 C20 -176.14(14) . . . . ? C16 C15 N3 C19 2.0(2) . . . . ? C14 C15 N3 C19 -175.98(14) . . . . ? C16 C15 N3 C20 178.20(13) . . . . ? C14 C15 N3 C20 0.3(2) . . . . ? C26 C20 N3 C19 69.36(18) . . . . ? C21 C20 N3 C19 -110.91(16) . . . . ? C26 C20 N3 C15 -106.96(16) . . . . ? C21 C20 N3 C15 72.78(18) . . . . ? S2 C24 N4 C23 -0.19(19) . . . . ? C22 C23 N4 C24 -178.27(15) . . . . ? C25 C23 N4 C24 0.33(19) . . . . ? C13 C12 S1 C11 176.33(15) . . . . ? C10 C12 S1 C11 0.76(12) . . . . ? N2 C11 S1 C12 0.08(14) . . . . ? N4 C24 S2 C25 0.00(15) . . . . ? C26 C25 S2 C24 177.80(16) . . . . ? C23 C25 S2 C24 0.18(12) . . . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 27.72 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.260 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.045 # Attachment '- co339-HL2.cif' data_co339 _database_code_depnum_ccdc_archive 'CCDC 798382' #TrackingRef '- co339-HL2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H16 N2 O3' _chemical_formula_weight 248.28 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.2835(4) _cell_length_b 13.9790(7) _cell_length_c 10.5581(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.255(2) _cell_angle_gamma 90.00 _cell_volume 1222.56(10) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4136 _cell_measurement_theta_min 2.86 _cell_measurement_theta_max 27.44 _exptl_crystal_description plate _exptl_crystal_colour pink _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.349 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.795 _exptl_absorpt_correction_T_max 0.990 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 X8 APEX II' _diffrn_measurement_method 'area detector' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12232 _diffrn_reflns_av_R_equivalents 0.0225 _diffrn_reflns_av_sigmaI/netI 0.0301 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 27.51 _reflns_number_total 5314 _reflns_number_gt 4571 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0463P)^2^+0.2043P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.5(9) _refine_ls_number_reflns 5314 _refine_ls_number_parameters 361 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0453 _refine_ls_R_factor_gt 0.0366 _refine_ls_wR_factor_ref 0.0931 _refine_ls_wR_factor_gt 0.0882 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _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 C1 C -0.2332(2) 0.43136(13) 0.49319(16) 0.0225(4) Uani 1 1 d . . . C2 C -0.2404(2) 0.38645(15) 0.37424(18) 0.0295(4) Uani 1 1 d . . . H2 H -0.3400 0.3607 0.3450 0.035 Uiso 1 1 calc R . . C3 C -0.1051(2) 0.37919(16) 0.29939(18) 0.0299(4) Uani 1 1 d . . . H3 H -0.1122 0.3489 0.2190 0.036 Uiso 1 1 calc R . . C4 C 0.0410(2) 0.41587(14) 0.34068(17) 0.0249(4) Uani 1 1 d . . . C5 C 0.0512(2) 0.46134(13) 0.45735(16) 0.0241(4) Uani 1 1 d . . . H5 H 0.1514 0.4868 0.4857 0.029 Uiso 1 1 calc R . . C6 C -0.0844(2) 0.46960(14) 0.53224(16) 0.0239(4) Uani 1 1 d . . . H6 H -0.0768 0.5016 0.6114 0.029 Uiso 1 1 calc R . . C7 C -0.5221(2) 0.40451(17) 0.5305(2) 0.0334(5) Uani 1 1 d . . . H7A H -0.5538 0.4362 0.4514 0.050 Uiso 1 1 calc R . . H7B H -0.6011 0.4194 0.5965 0.050 Uiso 1 1 calc R . . H7C H -0.5184 0.3352 0.5171 0.050 Uiso 1 1 calc R . . C8 C 0.2319(2) 0.48988(15) 0.19905(19) 0.0296(4) Uani 1 1 d . . . H8 H 0.1713 0.5471 0.2091 0.036 Uiso 1 1 calc R . . C9 C 0.3640(2) 0.49137(15) 0.12387(19) 0.0305(4) Uani 1 1 d . . . H9 H 0.3933 0.5491 0.0825 0.037 Uiso 1 1 calc R . . C10 C 0.4590(2) 0.40858(14) 0.10590(16) 0.0237(4) Uani 1 1 d . . . C11 C 0.4020(2) 0.32465(14) 0.17091(16) 0.0237(4) Uani 1 1 d . . . C12 C 0.2677(2) 0.32535(14) 0.24700(17) 0.0255(4) Uani 1 1 d . . . C13 C 0.2139(2) 0.23878(16) 0.3177(2) 0.0351(5) Uani 1 1 d . . . H13A H 0.1901 0.2563 0.4056 0.053 Uiso 1 1 calc R . . H13B H 0.2998 0.1905 0.3165 0.053 Uiso 1 1 calc R . . H13C H 0.1166 0.2126 0.2776 0.053 Uiso 1 1 calc R . . C14 C 0.3944(2) 0.68061(13) 0.36374(17) 0.0236(4) Uani 1 1 d . . . C15 C 0.3868(2) 0.73035(14) 0.24840(17) 0.0258(4) Uani 1 1 d . . . H15 H 0.2890 0.7605 0.2231 0.031 Uiso 1 1 calc R . . C16 C 0.5210(2) 0.73555(14) 0.17150(17) 0.0265(4) Uani 1 1 d . . . H16 H 0.5149 0.7697 0.0938 0.032 Uiso 1 1 calc R . . C17 C 0.6635(2) 0.69175(13) 0.20614(16) 0.0238(4) Uani 1 1 d . . . C18 C 0.6740(2) 0.64248(14) 0.32012(18) 0.0270(4) Uani 1 1 d . . . H18 H 0.7722 0.6122 0.3441 0.032 Uiso 1 1 calc R . . C19 C 0.5415(2) 0.63776(14) 0.39811(18) 0.0261(4) Uani 1 1 d . . . H19 H 0.5498 0.6049 0.4766 0.031 Uiso 1 1 calc R . . C20 C 0.1059(2) 0.70757(16) 0.4085(2) 0.0349(5) Uani 1 1 d . . . H20A H 0.1101 0.7771 0.3968 0.052 Uiso 1 1 calc R . . H20B H 0.0296 0.6921 0.4762 0.052 Uiso 1 1 calc R . . H20C H 0.0704 0.6772 0.3295 0.052 Uiso 1 1 calc R . . C21 C 0.8515(2) 0.61830(15) 0.06037(19) 0.0294(4) Uani 1 1 d . . . H21 H 0.7889 0.5616 0.0666 0.035 Uiso 1 1 calc R . . C22 C 0.9859(2) 0.61846(15) -0.0130(2) 0.0303(4) Uani 1 1 d . . . H22 H 1.0148 0.5619 -0.0573 0.036 Uiso 1 1 calc R . . C23 C 1.0838(2) 0.70100(14) -0.02487(16) 0.0246(4) Uani 1 1 d . . . C24 C 1.0297(2) 0.78275(14) 0.04487(16) 0.0234(4) Uani 1 1 d . . . C25 C 0.8934(2) 0.78092(13) 0.11803(17) 0.0235(4) Uani 1 1 d . . . C26 C 0.8409(2) 0.86622(15) 0.19302(19) 0.0322(4) Uani 1 1 d . . . H26A H 0.9270 0.9143 0.1931 0.048 Uiso 1 1 calc R . . H26B H 0.8181 0.8467 0.2803 0.048 Uiso 1 1 calc R . . H26C H 0.7432 0.8935 0.1548 0.048 Uiso 1 1 calc R . . N1 N -0.36558(18) 0.43793(13) 0.56914(16) 0.0296(4) Uani 1 1 d . . . N2 N 0.18275(18) 0.40989(12) 0.26047(14) 0.0258(3) Uani 1 1 d . . . N3 N 0.26432(19) 0.67265(14) 0.44229(16) 0.0323(4) Uani 1 1 d . . . N4 N 0.80462(18) 0.69777(11) 0.12518(14) 0.0250(3) Uani 1 1 d . . . O1 O 0.58491(15) 0.40613(10) 0.03766(12) 0.0279(3) Uani 1 1 d . . . O2 O 0.48423(17) 0.24104(10) 0.15831(13) 0.0320(3) Uani 1 1 d . . . O3 O 1.21122(16) 0.70575(10) -0.09144(13) 0.0317(3) Uani 1 1 d . . . O4 O 1.11568(16) 0.86535(10) 0.04031(14) 0.0312(3) Uani 1 1 d . . . O5 O 0.2611(2) 0.58620(13) 0.69887(15) 0.0434(4) Uani 1 1 d . . . O6 O 0.5666(2) 0.52558(14) 0.82188(15) 0.0417(4) Uani 1 1 d . . . H1N H -0.358(2) 0.4644(16) 0.642(2) 0.027(5) Uiso 1 1 d . . . H2O H 1.214(3) 0.8520(19) 0.001(2) 0.048(7) Uiso 1 1 d . . . H3N H 0.279(3) 0.6516(18) 0.523(2) 0.040(6) Uiso 1 1 d . . . H4O H 0.576(3) 0.2459(18) 0.121(2) 0.041(6) Uiso 1 1 d . . . H5A H 0.359(4) 0.555(3) 0.731(3) 0.081(10) Uiso 1 1 d . . . H5B H 0.236(3) 0.623(2) 0.764(3) 0.053(8) Uiso 1 1 d . . . H6A H 0.578(3) 0.584(3) 0.847(3) 0.067(9) Uiso 1 1 d . . . H6B H 0.576(4) 0.484(3) 0.893(3) 0.078(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 C1 0.0209(8) 0.0221(9) 0.0246(8) 0.0039(7) 0.0021(6) 0.0040(7) C2 0.0211(8) 0.0363(12) 0.0311(10) -0.0053(8) -0.0029(7) -0.0008(8) C3 0.0270(9) 0.0378(12) 0.0247(9) -0.0086(8) 0.0010(7) 0.0012(8) C4 0.0213(8) 0.0281(10) 0.0253(9) -0.0022(8) 0.0041(7) 0.0033(7) C5 0.0213(8) 0.0233(10) 0.0277(9) -0.0016(7) -0.0009(7) -0.0001(7) C6 0.0262(9) 0.0239(10) 0.0216(8) -0.0020(7) 0.0006(7) 0.0031(7) C7 0.0218(9) 0.0378(12) 0.0407(11) 0.0044(9) 0.0066(8) 0.0007(8) C8 0.0293(10) 0.0254(10) 0.0342(10) -0.0013(8) 0.0057(8) 0.0054(8) C9 0.0330(10) 0.0244(10) 0.0342(10) 0.0001(8) 0.0094(8) -0.0006(8) C10 0.0250(9) 0.0264(10) 0.0196(8) -0.0035(7) 0.0012(7) -0.0006(8) C11 0.0251(9) 0.0251(10) 0.0210(8) -0.0028(7) 0.0016(7) 0.0024(7) C12 0.0254(9) 0.0292(10) 0.0218(8) -0.0008(7) 0.0014(7) 0.0031(8) C13 0.0331(10) 0.0338(11) 0.0384(11) 0.0071(9) 0.0127(8) 0.0026(9) C14 0.0238(8) 0.0210(9) 0.0261(8) -0.0011(8) 0.0028(7) -0.0038(7) C15 0.0231(8) 0.0247(10) 0.0296(9) 0.0011(8) -0.0010(7) 0.0012(7) C16 0.0289(9) 0.0258(10) 0.0247(9) 0.0051(8) -0.0002(7) -0.0010(8) C17 0.0229(8) 0.0235(10) 0.0251(9) 0.0005(8) 0.0047(7) -0.0031(7) C18 0.0209(9) 0.0262(10) 0.0339(10) 0.0057(8) -0.0033(8) -0.0008(7) C19 0.0287(9) 0.0241(10) 0.0256(9) 0.0060(8) 0.0001(7) -0.0047(8) C20 0.0255(9) 0.0339(12) 0.0453(12) -0.0068(9) 0.0081(8) -0.0011(8) C21 0.0300(10) 0.0229(10) 0.0354(10) -0.0022(8) 0.0014(8) -0.0045(7) C22 0.0344(10) 0.0236(10) 0.0327(10) -0.0055(8) 0.0040(8) 0.0008(8) C23 0.0250(9) 0.0273(10) 0.0216(8) 0.0012(8) 0.0015(7) 0.0012(8) C24 0.0233(8) 0.0238(9) 0.0231(9) 0.0016(7) 0.0024(7) -0.0014(7) C25 0.0242(8) 0.0222(9) 0.0241(9) 0.0004(7) 0.0016(7) 0.0000(7) C26 0.0321(10) 0.0284(11) 0.0361(10) -0.0066(9) 0.0097(8) -0.0051(8) N1 0.0241(8) 0.0394(10) 0.0252(8) -0.0019(8) 0.0058(6) 0.0014(7) N2 0.0243(7) 0.0282(9) 0.0249(8) -0.0021(7) 0.0060(6) 0.0017(7) N3 0.0257(8) 0.0398(10) 0.0315(9) 0.0050(8) 0.0064(7) 0.0001(7) N4 0.0231(7) 0.0261(9) 0.0257(7) 0.0004(7) 0.0043(6) -0.0009(7) O1 0.0271(6) 0.0282(7) 0.0286(7) 0.0001(6) 0.0099(5) 0.0015(6) O2 0.0301(7) 0.0272(7) 0.0389(8) 0.0047(6) 0.0143(6) 0.0058(6) O3 0.0302(7) 0.0324(8) 0.0326(7) -0.0027(6) 0.0103(6) -0.0006(6) O4 0.0283(7) 0.0252(7) 0.0401(8) -0.0038(6) 0.0130(6) -0.0055(6) O5 0.0558(10) 0.0423(9) 0.0320(8) -0.0064(7) 0.0026(7) -0.0001(8) O6 0.0580(10) 0.0364(10) 0.0309(8) 0.0005(7) 0.0037(7) 0.0037(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 C1 N1 1.364(2) . ? C1 C6 1.404(2) . ? C1 C2 1.405(3) . ? C2 C3 1.378(3) . ? C2 H2 0.9500 . ? C3 C4 1.383(3) . ? C3 H3 0.9500 . ? C4 C5 1.388(3) . ? C4 N2 1.453(2) . ? C5 C6 1.381(2) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 N1 1.436(3) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C9 1.355(3) . ? C8 N2 1.356(3) . ? C8 H8 0.9500 . ? C9 C10 1.413(3) . ? C9 H9 0.9500 . ? C10 O1 1.270(2) . ? C10 C11 1.440(3) . ? C11 O2 1.360(2) . ? C11 C12 1.375(2) . ? C12 N2 1.383(2) . ? C12 C13 1.491(3) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 N3 1.367(2) . ? C14 C15 1.403(3) . ? C14 C19 1.404(3) . ? C15 C16 1.381(2) . ? C15 H15 0.9500 . ? C16 C17 1.378(3) . ? C16 H16 0.9500 . ? C17 C18 1.389(3) . ? C17 N4 1.454(2) . ? C18 C19 1.377(3) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C20 N3 1.444(3) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 C22 1.359(3) . ? C21 N4 1.362(3) . ? C21 H21 0.9500 . ? C22 C23 1.416(3) . ? C22 H22 0.9500 . ? C23 O3 1.272(2) . ? C23 C24 1.432(3) . ? C24 O4 1.358(2) . ? C24 C25 1.371(2) . ? C25 N4 1.378(2) . ? C25 C26 1.497(3) . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? N1 H1N 0.86(2) . ? N3 H3N 0.90(2) . ? O2 H4O 0.86(2) . ? O4 H2O 0.93(3) . ? O5 H5A 0.98(3) . ? O5 H5B 0.88(3) . ? O6 H6A 0.86(4) . ? O6 H6B 0.95(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 N1 C1 C6 120.58(17) . . ? N1 C1 C2 121.62(16) . . ? C6 C1 C2 117.80(15) . . ? C3 C2 C1 120.93(16) . . ? C3 C2 H2 119.5 . . ? C1 C2 H2 119.5 . . ? C2 C3 C4 120.32(17) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C3 C4 C5 119.91(16) . . ? C3 C4 N2 120.21(16) . . ? C5 C4 N2 119.85(16) . . ? C6 C5 C4 120.02(16) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C5 C6 C1 121.00(16) . . ? C5 C6 H6 119.5 . . ? C1 C6 H6 119.5 . . ? N1 C7 H7A 109.5 . . ? N1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C9 C8 N2 122.53(18) . . ? C9 C8 H8 118.7 . . ? N2 C8 H8 118.7 . . ? C8 C9 C10 121.20(18) . . ? C8 C9 H9 119.4 . . ? C10 C9 H9 119.4 . . ? O1 C10 C9 123.87(17) . . ? O1 C10 C11 121.36(17) . . ? C9 C10 C11 114.77(16) . . ? O2 C11 C12 118.05(17) . . ? O2 C11 C10 119.20(15) . . ? C12 C11 C10 122.74(17) . . ? C11 C12 N2 118.66(17) . . ? C11 C12 C13 122.09(17) . . ? N2 C12 C13 119.23(15) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N3 C14 C15 122.29(16) . . ? N3 C14 C19 119.60(17) . . ? C15 C14 C19 118.11(16) . . ? C16 C15 C14 120.19(16) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C17 C16 C15 120.76(17) . . ? C17 C16 H16 119.6 . . ? C15 C16 H16 119.6 . . ? C16 C17 C18 120.04(16) . . ? C16 C17 N4 120.57(16) . . ? C18 C17 N4 119.38(16) . . ? C19 C18 C17 119.66(16) . . ? C19 C18 H18 120.2 . . ? C17 C18 H18 120.2 . . ? C18 C19 C14 121.23(17) . . ? C18 C19 H19 119.4 . . ? C14 C19 H19 119.4 . . ? N3 C20 H20A 109.5 . . ? N3 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? N3 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C22 C21 N4 121.39(19) . . ? C22 C21 H21 119.3 . . ? N4 C21 H21 119.3 . . ? C21 C22 C23 121.53(19) . . ? C21 C22 H22 119.2 . . ? C23 C22 H22 119.2 . . ? O3 C23 C22 124.63(18) . . ? O3 C23 C24 120.30(17) . . ? C22 C23 C24 115.07(16) . . ? O4 C24 C25 117.99(17) . . ? O4 C24 C23 119.66(15) . . ? C25 C24 C23 122.34(17) . . ? C24 C25 N4 119.19(16) . . ? C24 C25 C26 121.66(17) . . ? N4 C25 C26 119.13(15) . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C1 N1 C7 122.55(17) . . ? C1 N1 H1N 120.1(14) . . ? C7 N1 H1N 117.3(14) . . ? C8 N2 C12 120.09(15) . . ? C8 N2 C4 118.44(16) . . ? C12 N2 C4 121.47(15) . . ? C14 N3 C20 122.71(18) . . ? C14 N3 H3N 119.4(14) . . ? C20 N3 H3N 117.4(14) . . ? C21 N4 C25 120.48(15) . . ? C21 N4 C17 118.68(16) . . ? C25 N4 C17 120.79(15) . . ? C11 O2 H4O 114.9(17) . . ? C24 O4 H2O 107.7(16) . . ? H5A O5 H5B 101(2) . . ? H6A O6 H6B 109(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 -179.07(19) . . . . ? C6 C1 C2 C3 0.8(3) . . . . ? C1 C2 C3 C4 0.3(3) . . . . ? C2 C3 C4 C5 -0.8(3) . . . . ? C2 C3 C4 N2 -178.72(18) . . . . ? C3 C4 C5 C6 0.2(3) . . . . ? N2 C4 C5 C6 178.13(17) . . . . ? C4 C5 C6 C1 0.9(3) . . . . ? N1 C1 C6 C5 178.47(17) . . . . ? C2 C1 C6 C5 -1.4(3) . . . . ? N2 C8 C9 C10 -0.3(3) . . . . ? C8 C9 C10 O1 -179.23(18) . . . . ? C8 C9 C10 C11 1.2(3) . . . . ? O1 C10 C11 O2 -0.3(3) . . . . ? C9 C10 C11 O2 179.23(16) . . . . ? O1 C10 C11 C12 178.94(16) . . . . ? C9 C10 C11 C12 -1.5(3) . . . . ? O2 C11 C12 N2 -179.89(16) . . . . ? C10 C11 C12 N2 0.8(3) . . . . ? O2 C11 C12 C13 1.8(3) . . . . ? C10 C11 C12 C13 -177.53(17) . . . . ? N3 C14 C15 C16 -179.28(18) . . . . ? C19 C14 C15 C16 0.6(3) . . . . ? C14 C15 C16 C17 0.4(3) . . . . ? C15 C16 C17 C18 -0.7(3) . . . . ? C15 C16 C17 N4 -179.73(17) . . . . ? C16 C17 C18 C19 -0.1(3) . . . . ? N4 C17 C18 C19 179.02(17) . . . . ? C17 C18 C19 C14 1.1(3) . . . . ? N3 C14 C19 C18 178.56(18) . . . . ? C15 C14 C19 C18 -1.3(3) . . . . ? N4 C21 C22 C23 0.3(3) . . . . ? C21 C22 C23 O3 179.71(19) . . . . ? C21 C22 C23 C24 -0.4(3) . . . . ? O3 C23 C24 O4 -0.4(3) . . . . ? C22 C23 C24 O4 179.65(16) . . . . ? O3 C23 C24 C25 -179.86(17) . . . . ? C22 C23 C24 C25 0.2(3) . . . . ? O4 C24 C25 N4 -179.46(16) . . . . ? C23 C24 C25 N4 0.0(3) . . . . ? O4 C24 C25 C26 -1.1(3) . . . . ? C23 C24 C25 C26 178.36(18) . . . . ? C6 C1 N1 C7 176.57(18) . . . . ? C2 C1 N1 C7 -3.5(3) . . . . ? C9 C8 N2 C12 -0.5(3) . . . . ? C9 C8 N2 C4 178.97(18) . . . . ? C11 C12 N2 C8 0.2(3) . . . . ? C13 C12 N2 C8 178.59(17) . . . . ? C11 C12 N2 C4 -179.22(16) . . . . ? C13 C12 N2 C4 -0.8(3) . . . . ? C3 C4 N2 C8 103.6(2) . . . . ? C5 C4 N2 C8 -74.2(2) . . . . ? C3 C4 N2 C12 -76.9(2) . . . . ? C5 C4 N2 C12 105.2(2) . . . . ? C15 C14 N3 C20 5.3(3) . . . . ? C19 C14 N3 C20 -174.52(19) . . . . ? C22 C21 N4 C25 -0.1(3) . . . . ? C22 C21 N4 C17 -177.46(17) . . . . ? C24 C25 N4 C21 0.0(3) . . . . ? C26 C25 N4 C21 -178.46(18) . . . . ? C24 C25 N4 C17 177.24(16) . . . . ? C26 C25 N4 C17 -1.2(2) . . . . ? C16 C17 N4 C21 -107.8(2) . . . . ? C18 C17 N4 C21 73.2(2) . . . . ? C16 C17 N4 C25 74.9(2) . . . . ? C18 C17 N4 C25 -104.2(2) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.243 _refine_diff_density_min -0.204 _refine_diff_density_rms 0.036 # Attachment '- co351-HL5-switched O2O1.cif' data_co351 _database_code_depnum_ccdc_archive 'CCDC 798383' #TrackingRef '- co351-HL5-switched O2O1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H10 N2 O2 S' _chemical_formula_weight 258.29 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/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 10.3006(12) _cell_length_b 7.8737(10) _cell_length_c 13.7999(16) _cell_angle_alpha 90.00 _cell_angle_beta 93.837(4) _cell_angle_gamma 90.00 _cell_volume 1116.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9704 _cell_measurement_theta_min 2.96 _cell_measurement_theta_max 27.98 _exptl_crystal_description needle _exptl_crystal_colour orange _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.536 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 0.284 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.867 _exptl_absorpt_correction_T_max 0.966 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 X8 APEX II' _diffrn_measurement_method 'area detector' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15521 _diffrn_reflns_av_R_equivalents 0.0220 _diffrn_reflns_av_sigmaI/netI 0.0140 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2541 _reflns_number_gt 2323 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0401P)^2^+0.7272P] 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 2541 _refine_ls_number_parameters 168 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0365 _refine_ls_R_factor_gt 0.0332 _refine_ls_wR_factor_ref 0.0882 _refine_ls_wR_factor_gt 0.0860 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _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 C1 C 0.74480(14) 0.00879(19) 0.43359(10) 0.0239(3) Uani 1 1 d . . . H1A H 0.7113 -0.0544 0.3760 0.036 Uiso 1 1 calc R . . H1B H 0.8396 -0.0034 0.4414 0.036 Uiso 1 1 calc R . . H1C H 0.7223 0.1292 0.4257 0.036 Uiso 1 1 calc R . . C2 C 0.68548(13) -0.05990(17) 0.52156(10) 0.0181(3) Uani 1 1 d . . . C3 C 0.60851(13) -0.20204(17) 0.51882(10) 0.0182(3) Uani 1 1 d . . . C4 C 0.54161(13) -0.26012(18) 0.60152(10) 0.0190(3) Uani 1 1 d . . . C5 C 0.56664(14) -0.1624(2) 0.68799(11) 0.0239(3) Uani 1 1 d . . . H5 H 0.5284 -0.1959 0.7458 0.029 Uiso 1 1 calc R . . C6 C 0.64353(14) -0.0231(2) 0.68932(10) 0.0239(3) Uani 1 1 d . . . H6 H 0.6564 0.0403 0.7477 0.029 Uiso 1 1 calc R . . C7 C 0.78466(13) 0.17547(18) 0.61730(10) 0.0196(3) Uani 1 1 d . . . C8 C 0.95547(13) 0.33947(18) 0.61329(10) 0.0195(3) Uani 1 1 d . . . C9 C 1.08245(14) 0.38932(19) 0.59760(11) 0.0240(3) Uani 1 1 d . . . H9 H 1.1428 0.3104 0.5743 0.029 Uiso 1 1 calc R . . C10 C 1.11860(14) 0.5556(2) 0.61661(11) 0.0262(3) Uani 1 1 d . . . H10 H 1.2044 0.5912 0.6053 0.031 Uiso 1 1 calc R . . C11 C 1.03156(16) 0.6723(2) 0.65203(11) 0.0279(3) Uani 1 1 d . . . H11 H 1.0594 0.7855 0.6648 0.033 Uiso 1 1 calc R . . C12 C 0.90561(16) 0.62635(19) 0.66889(11) 0.0262(3) Uani 1 1 d . . . H12 H 0.8464 0.7056 0.6934 0.031 Uiso 1 1 calc R . . C13 C 0.86883(13) 0.45855(19) 0.64846(10) 0.0205(3) Uani 1 1 d . . . N1 N 0.70337(11) 0.02896(15) 0.60883(8) 0.0200(3) Uani 1 1 d . . . N2 N 0.90504(11) 0.17619(15) 0.59666(9) 0.0215(3) Uani 1 1 d . . . O1 O 0.46596(10) -0.38571(13) 0.59501(8) 0.0247(2) Uani 1 1 d . . . O2 O 0.58990(11) -0.28691(14) 0.43373(7) 0.0259(2) Uani 1 1 d . . . S1 S 0.71808(3) 0.36428(5) 0.65775(3) 0.02483(12) Uani 1 1 d . . . H2O H 0.560(2) -0.377(3) 0.4431(18) 0.054(7) 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 C1 0.0300(7) 0.0200(7) 0.0223(7) 0.0003(5) 0.0061(6) -0.0069(6) C2 0.0179(6) 0.0169(6) 0.0197(6) -0.0007(5) 0.0024(5) -0.0001(5) C3 0.0193(6) 0.0171(6) 0.0183(6) -0.0016(5) 0.0011(5) -0.0010(5) C4 0.0162(6) 0.0181(6) 0.0231(7) -0.0004(5) 0.0036(5) 0.0003(5) C5 0.0242(7) 0.0274(8) 0.0211(7) -0.0026(6) 0.0081(5) -0.0054(6) C6 0.0236(7) 0.0273(7) 0.0214(7) -0.0068(6) 0.0055(5) -0.0045(6) C7 0.0196(6) 0.0181(6) 0.0211(7) -0.0037(5) 0.0018(5) -0.0020(5) C8 0.0195(6) 0.0192(7) 0.0194(6) 0.0003(5) -0.0008(5) -0.0021(5) C9 0.0190(6) 0.0257(7) 0.0273(7) 0.0029(6) 0.0010(5) -0.0008(5) C10 0.0228(7) 0.0306(8) 0.0246(7) 0.0037(6) -0.0022(6) -0.0098(6) C11 0.0367(8) 0.0227(7) 0.0238(7) -0.0019(6) -0.0009(6) -0.0115(6) C12 0.0317(8) 0.0219(7) 0.0252(7) -0.0046(6) 0.0023(6) -0.0020(6) C13 0.0192(6) 0.0230(7) 0.0193(7) -0.0011(5) 0.0006(5) -0.0034(5) N1 0.0193(5) 0.0192(6) 0.0218(6) -0.0041(4) 0.0046(4) -0.0047(4) N2 0.0201(6) 0.0201(6) 0.0244(6) -0.0012(5) 0.0017(5) -0.0037(5) O1 0.0259(5) 0.0195(5) 0.0295(6) -0.0031(4) 0.0080(4) -0.0072(4) O2 0.0365(6) 0.0217(5) 0.0199(5) -0.0039(4) 0.0051(4) -0.0127(5) S1 0.01861(18) 0.02168(19) 0.0347(2) -0.00754(14) 0.00548(14) -0.00211(13) _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 C1 C2 1.4963(19) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.3706(19) . ? C2 N1 1.3944(17) . ? C3 O2 1.3536(17) . ? C3 C4 1.4462(19) . ? C4 O1 1.2585(17) . ? C4 C5 1.429(2) . ? C5 C6 1.352(2) . ? C5 H5 0.9500 . ? C6 N1 1.3686(18) . ? C6 H6 0.9500 . ? C7 N2 1.2907(18) . ? C7 N1 1.4256(17) . ? C7 S1 1.7445(14) . ? C8 C9 1.3964(19) . ? C8 N2 1.3998(18) . ? C8 C13 1.403(2) . ? C9 C10 1.382(2) . ? C9 H9 0.9500 . ? C10 C11 1.395(2) . ? C10 H10 0.9500 . ? C11 C12 1.381(2) . ? C11 H11 0.9500 . ? C12 C13 1.398(2) . ? C12 H12 0.9500 . ? C13 S1 1.7335(14) . ? O2 H2O 0.79(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 C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 C2 N1 118.44(12) . . ? C3 C2 C1 122.66(12) . . ? N1 C2 C1 118.81(12) . . ? O2 C3 C2 118.36(12) . . ? O2 C3 C4 118.76(12) . . ? C2 C3 C4 122.80(12) . . ? O1 C4 C5 123.99(13) . . ? O1 C4 C3 121.17(13) . . ? C5 C4 C3 114.82(12) . . ? C6 C5 C4 121.39(13) . . ? C6 C5 H5 119.3 . . ? C4 C5 H5 119.3 . . ? C5 C6 N1 121.82(13) . . ? C5 C6 H6 119.1 . . ? N1 C6 H6 119.1 . . ? N2 C7 N1 123.58(13) . . ? N2 C7 S1 118.09(11) . . ? N1 C7 S1 118.33(10) . . ? C9 C8 N2 125.02(13) . . ? C9 C8 C13 119.33(13) . . ? N2 C8 C13 115.64(12) . . ? C10 C9 C8 118.70(14) . . ? C10 C9 H9 120.6 . . ? C8 C9 H9 120.6 . . ? C9 C10 C11 121.28(14) . . ? C9 C10 H10 119.4 . . ? C11 C10 H10 119.4 . . ? C12 C11 C10 121.32(14) . . ? C12 C11 H11 119.3 . . ? C10 C11 H11 119.3 . . ? C11 C12 C13 117.27(14) . . ? C11 C12 H12 121.4 . . ? C13 C12 H12 121.4 . . ? C12 C13 C8 122.09(13) . . ? C12 C13 S1 128.45(12) . . ? C8 C13 S1 109.45(10) . . ? C6 N1 C2 120.66(12) . . ? C6 N1 C7 118.02(12) . . ? C2 N1 C7 121.31(11) . . ? C7 N2 C8 108.62(12) . . ? C3 O2 H2O 109.7(18) . . ? C13 S1 C7 88.17(7) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C2 C3 O2 179.17(12) . . . . ? C1 C2 C3 O2 2.6(2) . . . . ? N1 C2 C3 C4 2.2(2) . . . . ? C1 C2 C3 C4 -174.31(13) . . . . ? O2 C3 C4 O1 -0.9(2) . . . . ? C2 C3 C4 O1 176.01(13) . . . . ? O2 C3 C4 C5 -179.71(12) . . . . ? C2 C3 C4 C5 -2.8(2) . . . . ? O1 C4 C5 C6 -176.41(14) . . . . ? C3 C4 C5 C6 2.3(2) . . . . ? C4 C5 C6 N1 -1.5(2) . . . . ? N2 C8 C9 C10 179.54(13) . . . . ? C13 C8 C9 C10 -0.5(2) . . . . ? C8 C9 C10 C11 0.9(2) . . . . ? C9 C10 C11 C12 -0.4(2) . . . . ? C10 C11 C12 C13 -0.4(2) . . . . ? C11 C12 C13 C8 0.7(2) . . . . ? C11 C12 C13 S1 -177.63(12) . . . . ? C9 C8 C13 C12 -0.3(2) . . . . ? N2 C8 C13 C12 179.67(13) . . . . ? C9 C8 C13 S1 178.34(11) . . . . ? N2 C8 C13 S1 -1.70(16) . . . . ? C5 C6 N1 C2 0.8(2) . . . . ? C5 C6 N1 C7 -178.87(14) . . . . ? C3 C2 N1 C6 -1.1(2) . . . . ? C1 C2 N1 C6 175.55(13) . . . . ? C3 C2 N1 C7 178.50(12) . . . . ? C1 C2 N1 C7 -4.83(19) . . . . ? N2 C7 N1 C6 124.06(15) . . . . ? S1 C7 N1 C6 -55.93(16) . . . . ? N2 C7 N1 C2 -55.57(19) . . . . ? S1 C7 N1 C2 124.44(12) . . . . ? N1 C7 N2 C8 -179.85(12) . . . . ? S1 C7 N2 C8 0.14(16) . . . . ? C9 C8 N2 C7 -179.01(14) . . . . ? C13 C8 N2 C7 1.03(17) . . . . ? C12 C13 S1 C7 179.90(14) . . . . ? C8 C13 S1 C7 1.39(11) . . . . ? N2 C7 S1 C13 -0.94(12) . . . . ? N1 C7 S1 C13 179.05(11) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.398 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.051 # Attachment '- co355-CuL3.cif' data_co355 _database_code_depnum_ccdc_archive 'CCDC 798384' #TrackingRef '- co355-CuL3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H34 Cu N4 O6 S2' _chemical_formula_weight 650.25 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 7.7458(9) _cell_length_b 16.433(2) _cell_length_c 12.0999(14) _cell_angle_alpha 90.00 _cell_angle_beta 103.182(4) _cell_angle_gamma 90.00 _cell_volume 1499.6(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7279 _cell_measurement_theta_min 3.02 _cell_measurement_theta_max 27.99 _exptl_crystal_description plate _exptl_crystal_colour green _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.440 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 678 _exptl_absorpt_coefficient_mu 0.915 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.651 _exptl_absorpt_correction_T_max 0.896 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 X8 APEX II' _diffrn_measurement_method 'area detector' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16222 _diffrn_reflns_av_R_equivalents 0.0452 _diffrn_reflns_av_sigmaI/netI 0.0389 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 28.13 _reflns_number_total 3618 _reflns_number_gt 3007 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0488P)^2^+0.4416P] 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 3618 _refine_ls_number_parameters 201 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0434 _refine_ls_R_factor_gt 0.0346 _refine_ls_wR_factor_ref 0.0979 _refine_ls_wR_factor_gt 0.0934 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _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 C1 C 0.5702(3) 0.20991(12) 0.4860(2) 0.0359(5) Uani 1 1 d . . . H1A H 0.5316 0.2533 0.4303 0.054 Uiso 1 1 calc R . . H1B H 0.6951 0.2181 0.5236 0.054 Uiso 1 1 calc R . . H1C H 0.4980 0.2112 0.5428 0.054 Uiso 1 1 calc R . . C2 C 0.5486(2) 0.12944(11) 0.42725(16) 0.0228(4) Uani 1 1 d . . . C3 C 0.6841(2) 0.07299(11) 0.44526(15) 0.0202(4) Uani 1 1 d . . . C4 C 0.6638(2) -0.00098(10) 0.38182(15) 0.0196(3) Uani 1 1 d . . . C5 C 0.5001(2) -0.01685(11) 0.30727(17) 0.0241(4) Uani 1 1 d . . . H5 H 0.4806 -0.0669 0.2672 0.029 Uiso 1 1 calc R . . C6 C 0.3691(2) 0.04023(11) 0.29284(16) 0.0248(4) Uani 1 1 d . . . H6 H 0.2590 0.0296 0.2414 0.030 Uiso 1 1 calc R . . C7 C 0.2510(2) 0.17211(11) 0.32401(16) 0.0216(4) Uani 1 1 d . . . C8 C 0.1506(2) 0.18908(12) 0.40222(16) 0.0259(4) Uani 1 1 d . . . H8 H 0.1709 0.1601 0.4720 0.031 Uiso 1 1 calc R . . C9 C 0.0209(2) 0.24819(12) 0.37860(16) 0.0272(4) Uani 1 1 d . . . H9 H -0.0481 0.2594 0.4324 0.033 Uiso 1 1 calc R . . C10 C -0.0104(2) 0.29176(11) 0.27682(16) 0.0240(4) Uani 1 1 d . . . C11 C 0.0910(3) 0.27315(11) 0.19868(16) 0.0266(4) Uani 1 1 d . . . H11 H 0.0705 0.3015 0.1285 0.032 Uiso 1 1 calc R . . C12 C 0.2212(2) 0.21384(12) 0.22213(16) 0.0255(4) Uani 1 1 d . . . H12 H 0.2899 0.2018 0.1684 0.031 Uiso 1 1 calc R . . N1 N 0.39174(19) 0.11184(9) 0.35005(13) 0.0219(3) Uani 1 1 d . . . N2 N -0.1397(3) 0.35011(12) 0.25309(18) 0.0369(4) Uani 1 1 d . . . O1 O 0.80107(16) -0.04839(7) 0.39495(11) 0.0248(3) Uani 1 1 d . . . O2 O 0.83968(16) 0.08509(8) 0.51671(11) 0.0247(3) Uani 1 1 d . . . O3 O 0.7297(3) 0.07684(12) -0.05551(14) 0.0571(5) Uani 1 1 d . . . Cu1 Cu 1.0000 0.0000 0.5000 0.01993(10) Uani 1 2 d S . . S1 S 0.83808(8) 0.05143(4) 0.05788(5) 0.0422(2) Uani 0.961(2) 1 d P A 1 C13 C 0.7590(4) 0.10778(16) 0.1602(2) 0.0525(7) Uani 0.961(2) 1 d P A 1 H13A H 0.7933 0.1650 0.1568 0.079 Uiso 0.961(2) 1 calc PR A 1 H13B H 0.8104 0.0860 0.2360 0.079 Uiso 0.961(2) 1 calc PR A 1 H13C H 0.6295 0.1037 0.1447 0.079 Uiso 0.961(2) 1 calc PR A 1 C14 C 0.7560(4) -0.04562(15) 0.0867(3) 0.0518(6) Uani 0.961(2) 1 d P A 1 H14A H 0.7890 -0.0864 0.0361 0.078 Uiso 0.961(2) 1 calc PR A 1 H14B H 0.6265 -0.0433 0.0741 0.078 Uiso 0.961(2) 1 calc PR A 1 H14C H 0.8071 -0.0606 0.1658 0.078 Uiso 0.961(2) 1 calc PR A 1 S1B S 0.696(2) 0.0478(11) 0.0523(16) 0.051(6) Uiso 0.039(2) 1 d P A 2 C13B C 0.7590(4) 0.10778(16) 0.1602(2) 0.0525(7) Uani 0.039(2) 1 d P A 2 H13D H 0.7234 0.1637 0.1379 0.079 Uiso 0.039(2) 1 calc PR A 2 H13E H 0.8883 0.1052 0.1864 0.079 Uiso 0.039(2) 1 calc PR A 2 H13F H 0.7037 0.0907 0.2217 0.079 Uiso 0.039(2) 1 calc PR A 2 C14B C 0.7560(4) -0.04562(15) 0.0867(3) 0.0518(6) Uani 0.039(2) 1 d P A 2 H14D H 0.7185 -0.0809 0.0202 0.078 Uiso 0.039(2) 1 calc PR A 2 H14E H 0.7004 -0.0641 0.1474 0.078 Uiso 0.039(2) 1 calc PR A 2 H14F H 0.8852 -0.0480 0.1131 0.078 Uiso 0.039(2) 1 calc PR A 2 H2A H -0.142(3) 0.3783(16) 0.193(2) 0.047(7) Uiso 1 1 d . . . H2B H -0.179(3) 0.3718(15) 0.307(2) 0.038(7) 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 C1 0.0292(10) 0.0278(10) 0.0460(14) -0.0155(9) -0.0015(9) 0.0055(8) C2 0.0229(8) 0.0206(8) 0.0239(10) -0.0025(7) 0.0036(7) 0.0006(7) C3 0.0211(8) 0.0208(8) 0.0182(9) -0.0006(7) 0.0035(6) -0.0004(6) C4 0.0211(8) 0.0170(8) 0.0203(9) 0.0023(6) 0.0044(6) 0.0016(6) C5 0.0232(8) 0.0196(8) 0.0277(10) -0.0039(7) 0.0017(7) -0.0018(6) C6 0.0209(8) 0.0238(9) 0.0281(10) -0.0017(7) 0.0020(7) -0.0026(7) C7 0.0203(8) 0.0204(8) 0.0236(10) 0.0015(7) 0.0039(7) 0.0023(6) C8 0.0293(9) 0.0288(10) 0.0205(9) 0.0076(7) 0.0073(7) 0.0059(7) C9 0.0277(9) 0.0345(10) 0.0214(10) 0.0044(8) 0.0093(7) 0.0092(8) C10 0.0246(8) 0.0239(9) 0.0222(10) 0.0016(7) 0.0029(7) 0.0031(7) C11 0.0328(10) 0.0271(9) 0.0201(10) 0.0058(7) 0.0064(7) 0.0031(8) C12 0.0274(9) 0.0278(10) 0.0237(10) 0.0009(7) 0.0108(7) 0.0030(7) N1 0.0204(7) 0.0209(7) 0.0234(8) -0.0002(6) 0.0029(6) 0.0028(6) N2 0.0444(10) 0.0412(11) 0.0262(10) 0.0099(8) 0.0101(8) 0.0237(8) O1 0.0217(6) 0.0196(6) 0.0299(7) -0.0048(5) -0.0007(5) 0.0033(5) O2 0.0213(6) 0.0242(6) 0.0259(7) -0.0070(5) 0.0000(5) 0.0032(5) O3 0.0711(12) 0.0726(13) 0.0265(9) 0.0084(8) 0.0092(8) -0.0217(10) Cu1 0.01897(16) 0.01953(16) 0.01977(18) -0.00165(11) 0.00128(11) 0.00257(11) S1 0.0325(3) 0.0567(4) 0.0384(4) 0.0006(3) 0.0101(2) -0.0093(3) C13 0.0733(17) 0.0461(15) 0.0400(14) -0.0005(11) 0.0170(12) -0.0169(13) C14 0.0594(16) 0.0378(13) 0.0587(18) 0.0046(11) 0.0146(13) 0.0061(11) C13B 0.0733(17) 0.0461(15) 0.0400(14) -0.0005(11) 0.0170(12) -0.0169(13) C14B 0.0594(16) 0.0378(13) 0.0587(18) 0.0046(11) 0.0146(13) 0.0061(11) _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 C1 C2 1.493(3) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.380(2) . ? C2 N1 1.384(2) . ? C3 O2 1.328(2) . ? C3 C4 1.427(2) . ? C4 O1 1.298(2) . ? C4 C5 1.403(2) . ? C5 C6 1.364(3) . ? C5 H5 0.9500 . ? C6 N1 1.356(2) . ? C6 H6 0.9500 . ? C7 C8 1.383(3) . ? C7 C12 1.383(3) . ? C7 N1 1.453(2) . ? C8 C9 1.380(2) . ? C8 H8 0.9500 . ? C9 C10 1.397(3) . ? C9 H9 0.9500 . ? C10 N2 1.369(2) . ? C10 C11 1.394(3) . ? C11 C12 1.385(3) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? N2 H2A 0.85(3) . ? N2 H2B 0.86(3) . ? O1 Cu1 1.9311(12) . ? O2 Cu1 1.9113(12) . ? O3 S1B 1.468(19) . ? O3 S1 1.4954(18) . ? Cu1 O2 1.9113(12) 3_756 ? Cu1 O1 1.9311(12) 3_756 ? S1 C13 1.764(3) . ? S1 C14 1.781(3) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? 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 C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 C2 N1 119.02(16) . . ? C3 C2 C1 121.44(16) . . ? N1 C2 C1 119.51(15) . . ? O2 C3 C2 123.13(16) . . ? O2 C3 C4 116.73(15) . . ? C2 C3 C4 120.07(15) . . ? O1 C4 C5 124.21(16) . . ? O1 C4 C3 117.30(15) . . ? C5 C4 C3 118.47(15) . . ? C6 C5 C4 119.45(16) . . ? C6 C5 H5 120.3 . . ? C4 C5 H5 120.3 . . ? N1 C6 C5 121.70(16) . . ? N1 C6 H6 119.2 . . ? C5 C6 H6 119.2 . . ? C8 C7 C12 120.29(16) . . ? C8 C7 N1 120.00(16) . . ? C12 C7 N1 119.69(16) . . ? C9 C8 C7 119.77(17) . . ? C9 C8 H8 120.1 . . ? C7 C8 H8 120.1 . . ? C8 C9 C10 121.03(18) . . ? C8 C9 H9 119.5 . . ? C10 C9 H9 119.5 . . ? N2 C10 C11 120.66(18) . . ? N2 C10 C9 121.05(18) . . ? C11 C10 C9 118.27(17) . . ? C12 C11 C10 120.82(17) . . ? C12 C11 H11 119.6 . . ? C10 C11 H11 119.6 . . ? C7 C12 C11 119.81(17) . . ? C7 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? C6 N1 C2 121.17(15) . . ? C6 N1 C7 118.50(14) . . ? C2 N1 C7 120.24(14) . . ? C10 N2 H2A 115.5(18) . . ? C10 N2 H2B 120.1(16) . . ? H2A N2 H2B 118(2) . . ? C4 O1 Cu1 109.99(10) . . ? C3 O2 Cu1 109.67(11) . . ? S1B O3 S1 43.2(7) . . ? O2 Cu1 O2 180.00(8) . 3_756 ? O2 Cu1 O1 93.97(5) . 3_756 ? O2 Cu1 O1 86.03(5) 3_756 3_756 ? O2 Cu1 O1 86.03(5) . . ? O2 Cu1 O1 93.97(5) 3_756 . ? O1 Cu1 O1 180.0 3_756 . ? O3 S1 C13 106.58(13) . . ? O3 S1 C14 106.19(12) . . ? C13 S1 C14 97.82(13) . . ? S1 C13 H13A 109.5 . . ? S1 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? S1 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? S1 C14 H14A 109.5 . . ? S1 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? S1 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C2 C3 O2 179.22(17) . . . . ? C1 C2 C3 O2 1.4(3) . . . . ? N1 C2 C3 C4 2.2(3) . . . . ? C1 C2 C3 C4 -175.57(19) . . . . ? O2 C3 C4 O1 -3.2(2) . . . . ? C2 C3 C4 O1 173.97(17) . . . . ? O2 C3 C4 C5 178.63(16) . . . . ? C2 C3 C4 C5 -4.2(3) . . . . ? O1 C4 C5 C6 -174.49(18) . . . . ? C3 C4 C5 C6 3.5(3) . . . . ? C4 C5 C6 N1 -1.0(3) . . . . ? C12 C7 C8 C9 -0.3(3) . . . . ? N1 C7 C8 C9 177.94(16) . . . . ? C7 C8 C9 C10 -0.3(3) . . . . ? C8 C9 C10 N2 179.65(19) . . . . ? C8 C9 C10 C11 1.0(3) . . . . ? N2 C10 C11 C12 -179.64(18) . . . . ? C9 C10 C11 C12 -0.9(3) . . . . ? C8 C7 C12 C11 0.4(3) . . . . ? N1 C7 C12 C11 -177.93(16) . . . . ? C10 C11 C12 C7 0.3(3) . . . . ? C5 C6 N1 C2 -1.1(3) . . . . ? C5 C6 N1 C7 175.51(18) . . . . ? C3 C2 N1 C6 0.4(3) . . . . ? C1 C2 N1 C6 178.27(19) . . . . ? C3 C2 N1 C7 -176.11(16) . . . . ? C1 C2 N1 C7 1.7(3) . . . . ? C8 C7 N1 C6 109.8(2) . . . . ? C12 C7 N1 C6 -71.9(2) . . . . ? C8 C7 N1 C2 -73.6(2) . . . . ? C12 C7 N1 C2 104.7(2) . . . . ? C5 C4 O1 Cu1 177.12(15) . . . . ? C3 C4 O1 Cu1 -0.9(2) . . . . ? C2 C3 O2 Cu1 -171.56(15) . . . . ? C4 C3 O2 Cu1 5.53(19) . . . . ? C3 O2 Cu1 O2 -57(83) . . . 3_756 ? C3 O2 Cu1 O1 175.24(12) . . . 3_756 ? C3 O2 Cu1 O1 -4.76(12) . . . . ? C4 O1 Cu1 O2 3.14(12) . . . . ? C4 O1 Cu1 O2 -176.86(12) . . . 3_756 ? C4 O1 Cu1 O1 150(5) . . . 3_756 ? S1B O3 S1 C13 -51.7(10) . . . . ? S1B O3 S1 C14 51.8(11) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 28.13 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.427 _refine_diff_density_min -0.356 _refine_diff_density_rms 0.067