# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H42 Cu N2 O3' _chemical_formula_sum 'C24 H42 Cu N2 O3' _chemical_formula_weight 470.15 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M P21/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 10.1575(3) _cell_length_b 24.1596(8) _cell_length_c 11.0644(3) _cell_angle_alpha 90.00 _cell_angle_beta 103.211(3) _cell_angle_gamma 90.00 _cell_volume 2643.36(14) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7982 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 0.00 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.03 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.012 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.181 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1265 _exptl_absorpt_coefficient_mu 0.850 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10305 _diffrn_reflns_av_R_equivalents 0.0292 _diffrn_reflns_av_unetI/netI 0.0483 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.98 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4650 _reflns_number_gt 3374 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4650 _refine_ls_number_parameters 282 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0677 _refine_ls_R_factor_gt 0.0460 _refine_ls_wR_factor_ref 0.1571 _refine_ls_wR_factor_gt 0.1338 _refine_ls_goodness_of_fit_ref 0.955 _refine_ls_restrained_S_all 0.955 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.14347(4) 0.247864(14) 0.87470(3) 0.03854(18) Uani 1 1 d . . . O2 O 0.3207(2) 0.27838(11) 0.8644(2) 0.0565(6) Uani 1 1 d . . . O1 O 0.1858(2) 0.17919(9) 0.8169(2) 0.0526(6) Uani 1 1 d . . . O3 O 0.3570(3) 0.24286(11) 1.0507(2) 0.0700(8) Uani 1 1 d . . . N2 N -0.0316(2) 0.22161(11) 0.9180(2) 0.0407(6) Uani 1 1 d . . . N1 N 0.0639(3) 0.32600(11) 0.8632(2) 0.0485(7) Uani 1 1 d . . . C9 C -0.0299(3) 0.13552(13) 0.7903(3) 0.0456(8) Uani 1 1 d . . . C11 C 0.1712(3) 0.08169(14) 0.7834(3) 0.0501(8) Uani 1 1 d . . . C8 C -0.0980(3) 0.18955(13) 0.8041(3) 0.0442(8) Uani 1 1 d . . . H8A H -0.0988 0.2121 0.7315 0.053 Uiso 1 1 calc R . . H8B H -0.1912 0.1823 0.8068 0.053 Uiso 1 1 calc R . . C10 C 0.1108(3) 0.13368(13) 0.7978(3) 0.0444(8) Uani 1 1 d . . . C13 C -0.0511(4) 0.03718(14) 0.7452(3) 0.0579(9) Uani 1 1 d . . . C12 C 0.0866(4) 0.03588(14) 0.7567(3) 0.0580(9) Uani 1 1 d . . . H12 H 0.1259 0.0020 0.7458 0.070 Uiso 1 1 calc R . . C1 C 0.1178(4) 0.35807(17) 0.9774(4) 0.0772(12) Uani 1 1 d . . . H1A H 0.2126 0.3647 0.9852 0.116 Uiso 1 1 calc R . . H1B H 0.1049 0.3376 1.0481 0.116 Uiso 1 1 calc R . . H1C H 0.0711 0.3928 0.9731 0.116 Uiso 1 1 calc R . . C5 C -0.0119(3) 0.18648(14) 1.0327(3) 0.0529(9) Uani 1 1 d . . . H5 H 0.0397 0.1538 1.0181 0.064 Uiso 1 1 calc R . . C14 C -0.1073(4) 0.08781(14) 0.7642(3) 0.0541(9) Uani 1 1 d . . . H14 H -0.1998 0.0899 0.7592 0.065 Uiso 1 1 calc R . . C4 C -0.1125(3) 0.27187(16) 0.9271(3) 0.0523(9) Uani 1 1 d . . . H4A H -0.0909 0.2853 1.0120 0.063 Uiso 1 1 calc R . . H4B H -0.2080 0.2627 0.9052 0.063 Uiso 1 1 calc R . . C3 C -0.0833(3) 0.31653(14) 0.8416(3) 0.0549(9) Uani 1 1 d . . . H3A H -0.1187 0.3056 0.7560 0.066 Uiso 1 1 calc R . . H3B H -0.1279 0.3506 0.8562 0.066 Uiso 1 1 calc R . . C2 C 0.0928(4) 0.35631(16) 0.7549(4) 0.0718(11) Uani 1 1 d . . . H2A H 0.0581 0.3356 0.6804 0.108 Uiso 1 1 calc R . . H2B H 0.1887 0.3609 0.7661 0.108 Uiso 1 1 calc R . . H2C H 0.0501 0.3920 0.7484 0.108 Uiso 1 1 calc R . . C6 C 0.0720(4) 0.21576(19) 1.1455(3) 0.0720(12) Uani 1 1 d . . . H6A H 0.1533 0.2298 1.1264 0.108 Uiso 1 1 calc R . . H6B H 0.0949 0.1901 1.2134 0.108 Uiso 1 1 calc R . . H6C H 0.0210 0.2459 1.1682 0.108 Uiso 1 1 calc R . . C7 C -0.1451(4) 0.1652(2) 1.0588(4) 0.0810(13) Uani 1 1 d . . . H7A H -0.2004 0.1961 1.0704 0.122 Uiso 1 1 calc R . . H7B H -0.1261 0.1429 1.1326 0.122 Uiso 1 1 calc R . . H7C H -0.1921 0.1434 0.9899 0.122 Uiso 1 1 calc R . . C15 C 0.3253(3) 0.07752(15) 0.7996(3) 0.0587(9) Uani 1 1 d . . . C19 C -0.1393(4) -0.01519(16) 0.7206(4) 0.0788(12) Uani 1 1 d . . . C18 C 0.3987(4) 0.09619(19) 0.9306(4) 0.0823(13) Uani 1 1 d . . . H18A H 0.4945 0.0923 0.9400 0.123 Uiso 1 1 calc R . . H18B H 0.3698 0.0737 0.9913 0.123 Uiso 1 1 calc R . . H18C H 0.3774 0.1342 0.9424 0.123 Uiso 1 1 calc R . . C17 C 0.3721(4) 0.11382(18) 0.7030(4) 0.0853(13) Uani 1 1 d . . . H17A H 0.3476 0.1516 0.7129 0.128 Uiso 1 1 calc R . . H17B H 0.3295 0.1014 0.6210 0.128 Uiso 1 1 calc R . . H17C H 0.4685 0.1111 0.7149 0.128 Uiso 1 1 calc R . . C22 C -0.0778(6) -0.0595(2) 0.6511(6) 0.136(2) Uani 1 1 d . . . H22A H 0.0086 -0.0705 0.7005 0.205 Uiso 1 1 calc R . . H22B H -0.0667 -0.0447 0.5735 0.205 Uiso 1 1 calc R . . H22C H -0.1369 -0.0910 0.6357 0.205 Uiso 1 1 calc R . . C20 C -0.2778(6) -0.0027(2) 0.6364(7) 0.166(3) Uani 1 1 d . . . H20A H -0.3243 -0.0368 0.6107 0.249 Uiso 1 1 calc R . . H20B H -0.2661 0.0174 0.5647 0.249 Uiso 1 1 calc R . . H20C H -0.3298 0.0192 0.6810 0.249 Uiso 1 1 calc R . . C21 C -0.1546(9) -0.0394(3) 0.8395(6) 0.183(4) Uani 1 1 d . . . H21A H -0.0671 -0.0485 0.8898 0.275 Uiso 1 1 calc R . . H21B H -0.2086 -0.0724 0.8233 0.275 Uiso 1 1 calc R . . H21C H -0.1981 -0.0131 0.8826 0.275 Uiso 1 1 calc R . . C16 C 0.3704(5) 0.01791(18) 0.7831(5) 0.0968(15) Uani 1 1 d . . . H16A H 0.3238 0.0043 0.7032 0.145 Uiso 1 1 calc R . . H16B H 0.3496 -0.0051 0.8469 0.145 Uiso 1 1 calc R . . H16C H 0.4662 0.0173 0.7887 0.145 Uiso 1 1 calc R . . C23 C 0.3974(3) 0.26700(16) 0.9684(3) 0.0520(8) Uani 1 1 d . . . C24 C 0.5414(4) 0.2861(2) 0.9915(4) 0.0991(17) Uani 1 1 d . . . H24A H 0.5762 0.2915 1.0790 0.149 Uiso 1 1 calc R . . H24B H 0.5456 0.3204 0.9488 0.149 Uiso 1 1 calc R . . H24C H 0.5946 0.2587 0.9616 0.149 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 0.0388(3) 0.0404(3) 0.0371(3) -0.00053(15) 0.00999(18) 0.00329(15) O2 0.0464(13) 0.0623(17) 0.0596(15) 0.0104(13) 0.0098(11) 0.0001(12) O1 0.0450(13) 0.0454(14) 0.0711(15) -0.0123(11) 0.0209(11) -0.0003(10) O3 0.080(2) 0.091(2) 0.0438(15) -0.0052(12) 0.0235(14) -0.0225(14) N2 0.0390(14) 0.0454(17) 0.0379(13) 0.0018(12) 0.0091(11) 0.0057(12) N1 0.0501(16) 0.0411(16) 0.0541(16) -0.0083(13) 0.0116(12) 0.0028(13) C9 0.0479(19) 0.0413(19) 0.0464(18) 0.0049(14) 0.0081(14) 0.0028(15) C11 0.057(2) 0.044(2) 0.0503(19) -0.0015(16) 0.0158(15) 0.0090(16) C8 0.0365(17) 0.048(2) 0.0456(17) 0.0033(15) 0.0036(13) 0.0029(14) C10 0.0473(19) 0.0416(19) 0.0442(18) 0.0006(15) 0.0105(14) -0.0016(15) C13 0.067(2) 0.041(2) 0.061(2) 0.0072(17) 0.0038(17) -0.0018(17) C12 0.072(3) 0.038(2) 0.067(2) 0.0007(17) 0.0211(18) 0.0087(17) C1 0.071(3) 0.068(3) 0.089(3) -0.036(2) 0.011(2) -0.002(2) C5 0.051(2) 0.066(2) 0.0432(17) 0.0133(16) 0.0121(14) 0.0099(17) C14 0.051(2) 0.049(2) 0.060(2) 0.0037(17) 0.0088(16) -0.0046(16) C4 0.044(2) 0.058(2) 0.056(2) -0.0091(18) 0.0129(15) 0.0095(17) C3 0.051(2) 0.048(2) 0.064(2) -0.0028(17) 0.0087(16) 0.0149(16) C2 0.080(3) 0.048(2) 0.093(3) 0.017(2) 0.030(2) 0.006(2) C6 0.063(2) 0.111(4) 0.0409(19) 0.009(2) 0.0088(16) 0.005(2) C7 0.063(3) 0.110(4) 0.074(3) 0.032(2) 0.025(2) -0.002(2) C15 0.054(2) 0.052(2) 0.073(2) -0.0038(18) 0.0215(18) 0.0109(16) C19 0.085(3) 0.041(2) 0.108(3) 0.002(2) 0.015(2) -0.011(2) C18 0.054(2) 0.095(3) 0.092(3) -0.004(3) 0.005(2) 0.017(2) C17 0.081(3) 0.092(3) 0.100(3) -0.005(3) 0.055(2) 0.005(2) C22 0.138(5) 0.076(4) 0.200(6) -0.047(4) 0.048(4) -0.037(3) C20 0.098(4) 0.067(4) 0.290(9) -0.012(5) -0.044(5) -0.022(3) C21 0.306(11) 0.114(5) 0.142(6) 0.003(4) 0.077(6) -0.119(6) C16 0.079(3) 0.068(3) 0.148(4) -0.013(3) 0.036(3) 0.021(2) C23 0.049(2) 0.061(2) 0.051(2) -0.0102(18) 0.0216(17) -0.0014(17) C24 0.046(2) 0.179(6) 0.073(3) 0.017(3) 0.0149(19) -0.015(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 O1 1.864(2) . ? Cu1 O2 1.972(2) . ? Cu1 N2 2.045(3) . ? Cu1 N1 2.046(3) . ? O2 C23 1.264(4) . ? O1 C10 1.327(4) . ? O3 C23 1.228(4) . ? N2 C4 1.482(4) . ? N2 C8 1.501(4) . ? N2 C5 1.502(4) . ? N1 C2 1.490(4) . ? N1 C3 1.477(4) . ? N1 C1 1.476(4) . ? C9 C10 1.414(4) . ? C9 C14 1.388(4) . ? C9 C8 1.501(4) . ? C11 C12 1.391(5) . ? C11 C10 1.423(4) . ? C11 C15 1.537(5) . ? C13 C12 1.376(5) . ? C13 C14 1.386(5) . ? C13 C19 1.538(5) . ? C5 C6 1.516(5) . ? C5 C7 1.536(5) . ? C4 C3 1.509(5) . ? C15 C17 1.539(5) . ? C15 C18 1.539(5) . ? C15 C16 1.535(5) . ? C19 C21 1.481(7) . ? C19 C20 1.529(7) . ? C19 C22 1.532(7) . ? C23 C24 1.500(5) . ? 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 O1 Cu1 O2 91.58(10) . . ? O1 Cu1 N2 94.92(10) . . ? O2 Cu1 N2 169.49(9) . . ? O1 Cu1 N1 156.79(10) . . ? O2 Cu1 N1 90.25(11) . . ? N2 Cu1 N1 87.04(11) . . ? C23 O2 Cu1 104.3(2) . . ? C10 O1 Cu1 128.5(2) . . ? C4 N2 C8 109.3(2) . . ? C4 N2 C5 112.0(2) . . ? C8 N2 C5 111.4(3) . . ? C4 N2 Cu1 106.7(2) . . ? C8 N2 Cu1 102.21(18) . . ? C5 N2 Cu1 114.68(18) . . ? C2 N1 C3 108.9(3) . . ? C2 N1 C1 109.1(3) . . ? C3 N1 C1 112.6(3) . . ? C2 N1 Cu1 110.8(2) . . ? C3 N1 Cu1 103.77(19) . . ? C1 N1 Cu1 111.5(2) . . ? C10 C9 C14 120.2(3) . . ? C10 C9 C8 120.3(3) . . ? C14 C9 C8 119.4(3) . . ? C12 C11 C10 117.7(3) . . ? C12 C11 C15 122.4(3) . . ? C10 C11 C15 119.9(3) . . ? N2 C8 C9 113.9(2) . . ? O1 C10 C9 121.3(3) . . ? O1 C10 C11 120.2(3) . . ? C9 C10 C11 118.5(3) . . ? C12 C13 C14 116.8(3) . . ? C12 C13 C19 122.4(3) . . ? C14 C13 C19 120.6(4) . . ? C13 C12 C11 124.6(3) . . ? N2 C5 C6 111.9(3) . . ? N2 C5 C7 113.3(3) . . ? C6 C5 C7 110.8(3) . . ? C13 C14 C9 122.1(3) . . ? N2 C4 C3 110.6(3) . . ? N1 C3 C4 110.2(3) . . ? C17 C15 C18 109.1(3) . . ? C17 C15 C16 107.7(3) . . ? C18 C15 C16 107.1(3) . . ? C17 C15 C11 110.5(3) . . ? C18 C15 C11 110.6(3) . . ? C16 C15 C11 111.8(3) . . ? C21 C19 C13 110.1(4) . . ? C21 C19 C20 110.5(6) . . ? C13 C19 C20 111.3(3) . . ? C21 C19 C22 107.9(5) . . ? C13 C19 C22 112.1(4) . . ? C20 C19 C22 104.8(5) . . ? O3 C23 O2 122.5(3) . . ? O3 C23 C24 119.9(3) . . ? O2 C23 C24 117.5(3) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.273 _refine_diff_density_min -0.389 _refine_diff_density_rms 0.054 _database_code_depnum_ccdc_archive 'CCDC 930722' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H58 Cu N2 O4' _chemical_formula_weight 646.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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 9.8751(13) _cell_length_b 13.671(2) _cell_length_c 14.078(2) _cell_angle_alpha 98.778(8) _cell_angle_beta 104.531(8) _cell_angle_gamma 96.777(8) _cell_volume 1793.8(4) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3287 _cell_measurement_theta_min 2.9744 _cell_measurement_theta_max 28.7143 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.197 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 698 _exptl_absorpt_coefficient_mu 0.647 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21263 _diffrn_reflns_av_R_equivalents 0.1169 _diffrn_reflns_av_unetI/netI 0.0810 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.52 _diffrn_reflns_theta_max 25.24 _reflns_number_total 6345 _reflns_number_gt 4341 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0100P)^2^+2.0000P] 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 6345 _refine_ls_number_parameters 404 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0671 _refine_ls_R_factor_gt 0.0477 _refine_ls_wR_factor_ref 0.1107 _refine_ls_wR_factor_gt 0.1045 _refine_ls_goodness_of_fit_ref 0.986 _refine_ls_restrained_S_all 0.986 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.15184(4) 0.59656(3) 0.19169(3) 0.03555(14) Uani 1 1 d . . . O1 O 0.0701(2) 0.45964(16) 0.16748(18) 0.0443(6) Uani 1 1 d . . . O2 O 0.0616(2) 0.62481(17) 0.29667(17) 0.0484(6) Uani 1 1 d . . . O3 O -0.1567(3) 0.6237(2) 0.2048(2) 0.0670(8) Uani 1 1 d . . . O4 O 0.6449(3) 0.73603(19) 0.21507(19) 0.0531(7) Uani 1 1 d . . . H4 H 0.7043 0.6993 0.2126 0.080 Uiso 1 1 calc R . . N1 N 0.1852(3) 0.74329(19) 0.1735(2) 0.0387(7) Uani 1 1 d . . . N2 N 0.3000(3) 0.57124(18) 0.11808(19) 0.0335(6) Uani 1 1 d . . . C1 C 0.0542(4) 0.7579(3) 0.1025(3) 0.0651(12) Uani 1 1 d . . . H1A H -0.0250 0.7439 0.1290 0.098 Uiso 1 1 calc R . . H1B H 0.0392 0.7133 0.0398 0.098 Uiso 1 1 calc R . . H1C H 0.0634 0.8260 0.0925 0.098 Uiso 1 1 calc R . . C2 C 0.2158(4) 0.8183(3) 0.2659(3) 0.0581(11) Uani 1 1 d . . . H2A H 0.2320 0.8843 0.2512 0.087 Uiso 1 1 calc R . . H2B H 0.2988 0.8072 0.3130 0.087 Uiso 1 1 calc R . . H2C H 0.1367 0.8124 0.2939 0.087 Uiso 1 1 calc R . . C3 C 0.3061(4) 0.7543(2) 0.1284(3) 0.0454(9) Uani 1 1 d . . . H3A H 0.3941 0.7755 0.1811 0.054 Uiso 1 1 calc R . . H3B H 0.2953 0.8055 0.0876 0.054 Uiso 1 1 calc R . . C4 C 0.3121(4) 0.6568(2) 0.0652(3) 0.0450(9) Uani 1 1 d . . . H4A H 0.2355 0.6442 0.0039 0.054 Uiso 1 1 calc R . . H4B H 0.4010 0.6619 0.0472 0.054 Uiso 1 1 calc R . . C5 C 0.2469(3) 0.4774(2) 0.0406(2) 0.0378(8) Uani 1 1 d . . . H5A H 0.3146 0.4692 0.0018 0.045 Uiso 1 1 calc R . . H5B H 0.1580 0.4845 -0.0044 0.045 Uiso 1 1 calc R . . C6 C 0.2241(3) 0.3848(2) 0.0839(2) 0.0349(8) Uani 1 1 d . . . C7 C 0.1315(3) 0.3812(2) 0.1448(2) 0.0353(8) Uani 1 1 d . . . C8 C 0.1015(3) 0.2905(2) 0.1794(2) 0.0355(8) Uani 1 1 d . . . C9 C 0.1650(3) 0.2104(2) 0.1489(2) 0.0398(8) Uani 1 1 d . . . H9 H 0.1441 0.1505 0.1699 0.048 Uiso 1 1 calc R . . C10 C 0.2577(3) 0.2135(2) 0.0889(2) 0.0376(8) Uani 1 1 d . . . C11 C 0.2855(3) 0.3026(2) 0.0574(2) 0.0376(8) Uani 1 1 d . . . H11 H 0.3471 0.3076 0.0174 0.045 Uiso 1 1 calc R . . C12 C 0.0019(3) 0.2821(2) 0.2472(3) 0.0411(8) Uani 1 1 d . . . C13 C -0.0127(5) 0.1785(3) 0.2766(3) 0.0675(12) Uani 1 1 d . . . H13A H -0.0531 0.1279 0.2176 0.101 Uiso 1 1 calc R . . H13B H -0.0732 0.1768 0.3203 0.101 Uiso 1 1 calc R . . H13C H 0.0792 0.1661 0.3103 0.101 Uiso 1 1 calc R . . C14 C -0.1458(4) 0.2988(3) 0.1935(3) 0.0591(11) Uani 1 1 d . . . H14A H -0.1400 0.3643 0.1767 0.089 Uiso 1 1 calc R . . H14B H -0.2070 0.2936 0.2364 0.089 Uiso 1 1 calc R . . H14C H -0.1834 0.2489 0.1336 0.089 Uiso 1 1 calc R . . C15 C 0.0611(4) 0.3597(3) 0.3441(3) 0.0564(10) Uani 1 1 d . . . H15A H 0.1515 0.3464 0.3795 0.085 Uiso 1 1 calc R . . H15B H -0.0032 0.3557 0.3849 0.085 Uiso 1 1 calc R . . H15C H 0.0721 0.4256 0.3286 0.085 Uiso 1 1 calc R . . C16 C 0.3229(4) 0.1208(2) 0.0573(3) 0.0472(9) Uani 1 1 d . . . C17 C 0.3597(10) 0.0647(5) 0.1399(5) 0.184(4) Uani 1 1 d . . . H17A H 0.3913 0.0042 0.1164 0.275 Uiso 1 1 calc R . . H17B H 0.2776 0.0482 0.1628 0.275 Uiso 1 1 calc R . . H17C H 0.4339 0.1055 0.1940 0.275 Uiso 1 1 calc R . . C18 C 0.2178(7) 0.0519(5) -0.0272(6) 0.198(5) Uani 1 1 d . . . H18A H 0.2050 0.0813 -0.0859 0.297 Uiso 1 1 calc R . . H18B H 0.1291 0.0405 -0.0112 0.297 Uiso 1 1 calc R . . H18C H 0.2513 -0.0107 -0.0393 0.297 Uiso 1 1 calc R . . C19 C 0.4526(7) 0.1473(4) 0.0269(7) 0.169(4) Uani 1 1 d . . . H19A H 0.4881 0.0873 0.0069 0.253 Uiso 1 1 calc R . . H19B H 0.5229 0.1899 0.0821 0.253 Uiso 1 1 calc R . . H19C H 0.4313 0.1819 -0.0281 0.253 Uiso 1 1 calc R . . C20 C -0.0710(4) 0.6184(3) 0.2838(3) 0.0477(9) Uani 1 1 d . . . C21 C -0.1204(5) 0.6029(3) 0.3744(3) 0.0768(14) Uani 1 1 d . . . H21A H -0.2205 0.6037 0.3601 0.115 Uiso 1 1 calc R . . H21B H -0.0711 0.6558 0.4298 0.115 Uiso 1 1 calc R . . H21C H -0.1009 0.5395 0.3908 0.115 Uiso 1 1 calc R . . C22 C 0.4400(3) 0.5615(2) 0.1864(2) 0.0398(8) Uani 1 1 d . . . H22A H 0.5118 0.5672 0.1506 0.048 Uiso 1 1 calc R . . H22B H 0.4328 0.4951 0.2028 0.048 Uiso 1 1 calc R . . C23 C 0.4888(3) 0.6382(2) 0.2824(2) 0.0339(8) Uani 1 1 d . . . C24 C 0.5895(3) 0.7232(2) 0.2937(3) 0.0365(8) Uani 1 1 d . . . C25 C 0.6264(3) 0.7978(2) 0.3805(3) 0.0403(8) Uani 1 1 d . . . C26 C 0.5666(3) 0.7790(3) 0.4561(3) 0.0434(9) Uani 1 1 d . . . H26 H 0.5922 0.8266 0.5150 0.052 Uiso 1 1 calc R . . C27 C 0.4693(3) 0.6924(2) 0.4500(2) 0.0384(8) Uani 1 1 d . . . C28 C 0.4321(3) 0.6244(2) 0.3612(2) 0.0359(8) Uani 1 1 d . . . H28 H 0.3666 0.5671 0.3537 0.043 Uiso 1 1 calc R . . C29 C 0.7234(4) 0.8981(3) 0.3902(3) 0.0536(10) Uani 1 1 d . . . C30 C 0.6528(5) 0.9526(3) 0.3086(3) 0.0718(13) Uani 1 1 d . . . H30A H 0.6413 0.9122 0.2442 0.108 Uiso 1 1 calc R . . H30B H 0.7113 1.0157 0.3144 0.108 Uiso 1 1 calc R . . H30C H 0.5617 0.9641 0.3161 0.108 Uiso 1 1 calc R . . C31 C 0.8693(4) 0.8804(3) 0.3799(4) 0.0913(17) Uani 1 1 d . . . H31A H 0.9134 0.8470 0.4319 0.137 Uiso 1 1 calc R . . H31B H 0.9273 0.9436 0.3854 0.137 Uiso 1 1 calc R . . H31C H 0.8591 0.8394 0.3160 0.137 Uiso 1 1 calc R . . C32 C 0.7444(5) 0.9673(3) 0.4914(3) 0.0765(14) Uani 1 1 d . . . H32A H 0.6540 0.9809 0.4988 0.115 Uiso 1 1 calc R . . H32B H 0.8038 1.0292 0.4942 0.115 Uiso 1 1 calc R . . H32C H 0.7886 0.9352 0.5443 0.115 Uiso 1 1 calc R . . C33 C 0.4098(4) 0.6804(3) 0.5389(3) 0.0458(9) Uani 1 1 d . . . C34 C 0.3112(5) 0.5799(3) 0.5205(3) 0.0799(14) Uani 1 1 d . . . H34A H 0.2357 0.5740 0.4607 0.120 Uiso 1 1 calc R . . H34B H 0.2722 0.5770 0.5762 0.120 Uiso 1 1 calc R . . H34C H 0.3640 0.5259 0.5132 0.120 Uiso 1 1 calc R . . C35 C 0.3241(5) 0.7633(3) 0.5563(4) 0.0879(15) Uani 1 1 d . . . H35A H 0.3850 0.8272 0.5733 0.132 Uiso 1 1 calc R . . H35B H 0.2832 0.7541 0.6100 0.132 Uiso 1 1 calc R . . H35C H 0.2499 0.7610 0.4966 0.132 Uiso 1 1 calc R . . C36 C 0.5307(5) 0.6839(4) 0.6325(3) 0.0879(15) Uani 1 1 d . . . H36A H 0.5858 0.6326 0.6197 0.132 Uiso 1 1 calc R . . H36B H 0.4920 0.6729 0.6869 0.132 Uiso 1 1 calc R . . H36C H 0.5901 0.7484 0.6498 0.132 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 0.0367(2) 0.0352(3) 0.0382(3) 0.01185(19) 0.01394(18) 0.00514(17) O1 0.0489(13) 0.0310(13) 0.0619(17) 0.0128(12) 0.0311(12) 0.0018(11) O2 0.0480(14) 0.0561(16) 0.0475(16) 0.0106(12) 0.0229(12) 0.0115(12) O3 0.0593(17) 0.103(2) 0.0497(18) 0.0222(16) 0.0232(14) 0.0275(16) O4 0.0472(15) 0.0571(17) 0.0635(18) 0.0216(14) 0.0253(13) 0.0064(12) N1 0.0399(15) 0.0332(16) 0.0440(18) 0.0139(14) 0.0092(13) 0.0063(12) N2 0.0416(15) 0.0287(15) 0.0326(16) 0.0119(12) 0.0132(12) 0.0004(12) C1 0.045(2) 0.068(3) 0.082(3) 0.041(2) 0.002(2) 0.006(2) C2 0.071(3) 0.039(2) 0.063(3) 0.006(2) 0.019(2) 0.0042(19) C3 0.047(2) 0.034(2) 0.059(2) 0.0214(18) 0.0164(18) 0.0029(16) C4 0.058(2) 0.038(2) 0.046(2) 0.0194(18) 0.0225(18) 0.0037(17) C5 0.0461(19) 0.037(2) 0.0312(19) 0.0056(16) 0.0157(15) 0.0016(15) C6 0.0394(17) 0.0329(19) 0.0317(19) 0.0084(15) 0.0109(15) -0.0023(15) C7 0.0369(17) 0.035(2) 0.0328(19) 0.0044(16) 0.0114(15) -0.0027(15) C8 0.0367(17) 0.036(2) 0.0330(19) 0.0073(16) 0.0119(15) -0.0036(15) C9 0.0464(19) 0.034(2) 0.040(2) 0.0130(16) 0.0126(16) 0.0001(16) C10 0.0414(18) 0.033(2) 0.038(2) 0.0077(16) 0.0116(15) 0.0012(15) C11 0.0404(18) 0.039(2) 0.035(2) 0.0060(16) 0.0165(15) -0.0005(15) C12 0.0468(19) 0.041(2) 0.040(2) 0.0141(17) 0.0186(16) -0.0019(16) C13 0.090(3) 0.058(3) 0.074(3) 0.030(2) 0.052(3) 0.006(2) C14 0.046(2) 0.078(3) 0.059(3) 0.024(2) 0.0228(19) -0.0008(19) C15 0.062(2) 0.065(3) 0.047(2) 0.012(2) 0.0260(19) 0.005(2) C16 0.056(2) 0.032(2) 0.059(3) 0.0114(19) 0.0239(19) 0.0080(17) C17 0.363(12) 0.155(6) 0.155(6) 0.111(5) 0.171(8) 0.199(7) C18 0.142(6) 0.137(6) 0.227(9) -0.124(6) -0.038(6) 0.078(5) C19 0.137(5) 0.073(4) 0.375(12) 0.068(5) 0.179(7) 0.054(4) C20 0.058(2) 0.045(2) 0.051(3) 0.0116(19) 0.030(2) 0.0154(18) C21 0.079(3) 0.102(4) 0.082(3) 0.048(3) 0.052(3) 0.036(3) C22 0.0394(18) 0.038(2) 0.044(2) 0.0081(17) 0.0169(16) 0.0030(15) C23 0.0321(16) 0.0293(18) 0.040(2) 0.0079(15) 0.0087(14) 0.0047(14) C24 0.0310(16) 0.037(2) 0.044(2) 0.0133(17) 0.0123(15) 0.0040(14) C25 0.0306(17) 0.040(2) 0.048(2) 0.0109(18) 0.0053(16) 0.0017(15) C26 0.0416(19) 0.040(2) 0.042(2) 0.0043(17) 0.0028(16) 0.0038(16) C27 0.0358(17) 0.044(2) 0.036(2) 0.0126(17) 0.0086(15) 0.0080(15) C28 0.0322(16) 0.0311(19) 0.044(2) 0.0124(17) 0.0088(15) 0.0021(14) C29 0.046(2) 0.038(2) 0.068(3) 0.010(2) 0.0086(19) -0.0084(17) C30 0.087(3) 0.045(2) 0.078(3) 0.019(2) 0.017(3) -0.008(2) C31 0.044(2) 0.068(3) 0.150(5) 0.008(3) 0.023(3) -0.015(2) C32 0.082(3) 0.048(3) 0.077(3) 0.001(2) 0.002(3) -0.018(2) C33 0.053(2) 0.046(2) 0.038(2) 0.0096(17) 0.0126(17) 0.0047(17) C34 0.101(3) 0.077(3) 0.066(3) 0.019(3) 0.042(3) -0.014(3) C35 0.112(4) 0.092(4) 0.095(4) 0.035(3) 0.070(3) 0.043(3) C36 0.087(3) 0.126(4) 0.048(3) 0.025(3) 0.012(2) 0.007(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 O1 1.893(2) . ? Cu1 O2 1.922(2) . ? Cu1 N2 2.026(3) . ? Cu1 N1 2.059(3) . ? O1 C7 1.328(4) . ? O2 C20 1.266(4) . ? O3 C20 1.234(4) . ? O4 C24 1.377(4) . ? O4 H4 0.8200 . ? N1 C2 1.469(4) . ? N1 C1 1.478(4) . ? N1 C3 1.489(4) . ? N2 C4 1.489(4) . ? N2 C5 1.495(4) . ? N2 C22 1.506(4) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C3 C4 1.502(5) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.505(4) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C11 1.384(4) . ? C6 C7 1.403(4) . ? C7 C8 1.426(4) . ? C8 C9 1.389(4) . ? C8 C12 1.540(4) . ? C9 C10 1.395(4) . ? C9 H9 0.9300 . ? C10 C11 1.380(4) . ? C10 C16 1.543(5) . ? C11 H11 0.9300 . ? C12 C14 1.526(5) . ? C12 C15 1.529(5) . ? C12 C13 1.535(5) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 C19 1.472(6) . ? C16 C18 1.478(6) . ? C16 C17 1.483(6) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 C21 1.510(5) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 C23 1.510(4) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C28 1.388(4) . ? C23 C24 1.400(4) . ? C24 C25 1.405(5) . ? C25 C26 1.383(5) . ? C25 C29 1.544(4) . ? C26 C27 1.411(4) . ? C26 H26 0.9300 . ? C27 C28 1.377(4) . ? C27 C33 1.532(5) . ? C28 H28 0.9300 . ? C29 C31 1.528(5) . ? C29 C30 1.531(5) . ? C29 C32 1.536(5) . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C33 C35 1.518(5) . ? C33 C36 1.531(5) . ? C33 C34 1.533(5) . ? C34 H34A 0.9600 . ? C34 H34B 0.9600 . ? C34 H34C 0.9600 . ? C35 H35A 0.9600 . ? C35 H35B 0.9600 . ? C35 H35C 0.9600 . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 O2 90.04(10) . . ? O1 Cu1 N2 94.31(9) . . ? O2 Cu1 N2 162.15(10) . . ? O1 Cu1 N1 159.98(11) . . ? O2 Cu1 N1 94.60(11) . . ? N2 Cu1 N1 87.21(10) . . ? C7 O1 Cu1 126.60(19) . . ? C20 O2 Cu1 124.8(2) . . ? C24 O4 H4 109.5 . . ? C2 N1 C1 109.5(3) . . ? C2 N1 C3 109.5(3) . . ? C1 N1 C3 109.9(3) . . ? C2 N1 Cu1 114.7(2) . . ? C1 N1 Cu1 106.1(2) . . ? C3 N1 Cu1 107.0(2) . . ? C4 N2 C5 107.7(2) . . ? C4 N2 C22 112.4(2) . . ? C5 N2 C22 109.0(2) . . ? C4 N2 Cu1 105.27(19) . . ? C5 N2 Cu1 109.46(17) . . ? C22 N2 Cu1 112.91(19) . . ? N1 C1 H1A 109.5 . . ? N1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? N1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 H2A 109.5 . . ? N1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? N1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? N1 C3 C4 110.7(3) . . ? N1 C3 H3A 109.5 . . ? C4 C3 H3A 109.5 . . ? N1 C3 H3B 109.5 . . ? C4 C3 H3B 109.5 . . ? H3A C3 H3B 108.1 . . ? N2 C4 C3 111.9(3) . . ? N2 C4 H4A 109.2 . . ? C3 C4 H4A 109.2 . . ? N2 C4 H4B 109.2 . . ? C3 C4 H4B 109.2 . . ? H4A C4 H4B 107.9 . . ? N2 C5 C6 113.4(3) . . ? N2 C5 H5A 108.9 . . ? C6 C5 H5A 108.9 . . ? N2 C5 H5B 108.9 . . ? C6 C5 H5B 108.9 . . ? H5A C5 H5B 107.7 . . ? C11 C6 C7 121.4(3) . . ? C11 C6 C5 119.9(3) . . ? C7 C6 C5 118.6(3) . . ? O1 C7 C6 120.8(3) . . ? O1 C7 C8 120.7(3) . . ? C6 C7 C8 118.5(3) . . ? C9 C8 C7 117.3(3) . . ? C9 C8 C12 121.7(3) . . ? C7 C8 C12 121.0(3) . . ? C8 C9 C10 124.5(3) . . ? C8 C9 H9 117.7 . . ? C10 C9 H9 117.7 . . ? C11 C10 C9 116.7(3) . . ? C11 C10 C16 121.8(3) . . ? C9 C10 C16 121.5(3) . . ? C10 C11 C6 121.6(3) . . ? C10 C11 H11 119.2 . . ? C6 C11 H11 119.2 . . ? C14 C12 C15 109.8(3) . . ? C14 C12 C13 107.9(3) . . ? C15 C12 C13 107.1(3) . . ? C14 C12 C8 110.1(3) . . ? C15 C12 C8 109.9(3) . . ? C13 C12 C8 111.9(3) . . ? 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 . . ? C12 C14 H14A 109.5 . . ? C12 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C12 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C12 C15 H15A 109.5 . . ? C12 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C12 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C19 C16 C18 108.7(6) . . ? C19 C16 C17 107.6(5) . . ? C18 C16 C17 107.3(5) . . ? C19 C16 C10 112.6(3) . . ? C18 C16 C10 109.3(3) . . ? C17 C16 C10 111.1(3) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O3 C20 O2 124.7(3) . . ? O3 C20 C21 120.7(3) . . ? O2 C20 C21 114.6(4) . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? N2 C22 C23 114.7(3) . . ? N2 C22 H22A 108.6 . . ? C23 C22 H22A 108.6 . . ? N2 C22 H22B 108.6 . . ? C23 C22 H22B 108.6 . . ? H22A C22 H22B 107.6 . . ? C28 C23 C24 119.2(3) . . ? C28 C23 C22 119.5(3) . . ? C24 C23 C22 121.4(3) . . ? O4 C24 C23 118.6(3) . . ? O4 C24 C25 120.3(3) . . ? C23 C24 C25 120.9(3) . . ? C26 C25 C24 116.7(3) . . ? C26 C25 C29 121.0(3) . . ? C24 C25 C29 122.2(3) . . ? C25 C26 C27 124.4(3) . . ? C25 C26 H26 117.8 . . ? C27 C26 H26 117.8 . . ? C28 C27 C26 116.2(3) . . ? C28 C27 C33 124.3(3) . . ? C26 C27 C33 119.5(3) . . ? C27 C28 C23 122.5(3) . . ? C27 C28 H28 118.7 . . ? C23 C28 H28 118.7 . . ? C31 C29 C30 110.0(4) . . ? C31 C29 C32 108.0(3) . . ? C30 C29 C32 107.4(3) . . ? C31 C29 C25 111.0(3) . . ? C30 C29 C25 108.5(3) . . ? C32 C29 C25 111.9(3) . . ? C29 C30 H30A 109.5 . . ? C29 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C29 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C29 C31 H31A 109.5 . . ? C29 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C29 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C29 C32 H32A 109.5 . . ? C29 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C29 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C35 C33 C36 110.4(4) . . ? C35 C33 C27 109.3(3) . . ? C36 C33 C27 110.2(3) . . ? C35 C33 C34 107.5(3) . . ? C36 C33 C34 107.2(3) . . ? C27 C33 C34 112.1(3) . . ? C33 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C33 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C33 C35 H35A 109.5 . . ? C33 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C33 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C33 C36 H36A 109.5 . . ? C33 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C33 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 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 O2 Cu1 O1 C7 -141.3(3) . . . . ? N2 Cu1 O1 C7 21.3(3) . . . . ? N1 Cu1 O1 C7 115.0(3) . . . . ? O1 Cu1 O2 C20 -66.6(3) . . . . ? N2 Cu1 O2 C20 -170.9(3) . . . . ? N1 Cu1 O2 C20 93.9(3) . . . . ? O1 Cu1 N1 C2 137.3(3) . . . . ? O2 Cu1 N1 C2 34.4(2) . . . . ? N2 Cu1 N1 C2 -127.8(2) . . . . ? O1 Cu1 N1 C1 16.3(4) . . . . ? O2 Cu1 N1 C1 -86.5(2) . . . . ? N2 Cu1 N1 C1 111.3(2) . . . . ? O1 Cu1 N1 C3 -100.9(3) . . . . ? O2 Cu1 N1 C3 156.2(2) . . . . ? N2 Cu1 N1 C3 -6.0(2) . . . . ? O1 Cu1 N2 C4 141.9(2) . . . . ? O2 Cu1 N2 C4 -114.5(3) . . . . ? N1 Cu1 N2 C4 -18.1(2) . . . . ? O1 Cu1 N2 C5 26.3(2) . . . . ? O2 Cu1 N2 C5 130.0(3) . . . . ? N1 Cu1 N2 C5 -133.7(2) . . . . ? O1 Cu1 N2 C22 -95.2(2) . . . . ? O2 Cu1 N2 C22 8.4(4) . . . . ? N1 Cu1 N2 C22 104.8(2) . . . . ? C2 N1 C3 C4 154.4(3) . . . . ? C1 N1 C3 C4 -85.3(3) . . . . ? Cu1 N1 C3 C4 29.4(3) . . . . ? C5 N2 C4 C3 156.7(3) . . . . ? C22 N2 C4 C3 -83.3(3) . . . . ? Cu1 N2 C4 C3 40.0(3) . . . . ? N1 C3 C4 N2 -48.0(4) . . . . ? C4 N2 C5 C6 -177.7(3) . . . . ? C22 N2 C5 C6 60.2(3) . . . . ? Cu1 N2 C5 C6 -63.7(3) . . . . ? N2 C5 C6 C11 -127.3(3) . . . . ? N2 C5 C6 C7 57.4(4) . . . . ? Cu1 O1 C7 C6 -36.2(4) . . . . ? Cu1 O1 C7 C8 145.6(2) . . . . ? C11 C6 C7 O1 -178.1(3) . . . . ? C5 C6 C7 O1 -3.0(5) . . . . ? C11 C6 C7 C8 0.1(5) . . . . ? C5 C6 C7 C8 175.2(3) . . . . ? O1 C7 C8 C9 177.2(3) . . . . ? C6 C7 C8 C9 -1.0(4) . . . . ? O1 C7 C8 C12 -2.4(5) . . . . ? C6 C7 C8 C12 179.4(3) . . . . ? C7 C8 C9 C10 1.4(5) . . . . ? C12 C8 C9 C10 -179.0(3) . . . . ? C8 C9 C10 C11 -0.9(5) . . . . ? C8 C9 C10 C16 -179.4(3) . . . . ? C9 C10 C11 C6 -0.2(5) . . . . ? C16 C10 C11 C6 178.4(3) . . . . ? C7 C6 C11 C10 0.5(5) . . . . ? C5 C6 C11 C10 -174.6(3) . . . . ? C9 C8 C12 C14 -118.6(4) . . . . ? C7 C8 C12 C14 61.0(4) . . . . ? C9 C8 C12 C15 120.3(3) . . . . ? C7 C8 C12 C15 -60.1(4) . . . . ? C9 C8 C12 C13 1.4(5) . . . . ? C7 C8 C12 C13 -179.0(3) . . . . ? C11 C10 C16 C19 22.3(6) . . . . ? C9 C10 C16 C19 -159.2(5) . . . . ? C11 C10 C16 C18 -98.7(5) . . . . ? C9 C10 C16 C18 79.8(6) . . . . ? C11 C10 C16 C17 143.1(5) . . . . ? C9 C10 C16 C17 -38.4(6) . . . . ? Cu1 O2 C20 O3 -23.3(5) . . . . ? Cu1 O2 C20 C21 156.5(3) . . . . ? C4 N2 C22 C23 75.3(3) . . . . ? C5 N2 C22 C23 -165.4(2) . . . . ? Cu1 N2 C22 C23 -43.6(3) . . . . ? N2 C22 C23 C28 79.9(4) . . . . ? N2 C22 C23 C24 -99.8(3) . . . . ? C28 C23 C24 O4 -180.0(3) . . . . ? C22 C23 C24 O4 -0.3(5) . . . . ? C28 C23 C24 C25 -4.5(5) . . . . ? C22 C23 C24 C25 175.2(3) . . . . ? O4 C24 C25 C26 -179.8(3) . . . . ? C23 C24 C25 C26 4.8(5) . . . . ? O4 C24 C25 C29 2.8(5) . . . . ? C23 C24 C25 C29 -172.6(3) . . . . ? C24 C25 C26 C27 -2.0(5) . . . . ? C29 C25 C26 C27 175.4(3) . . . . ? C25 C26 C27 C28 -1.0(5) . . . . ? C25 C26 C27 C33 -179.7(3) . . . . ? C26 C27 C28 C23 1.4(5) . . . . ? C33 C27 C28 C23 -179.9(3) . . . . ? C24 C23 C28 C27 1.2(5) . . . . ? C22 C23 C28 C27 -178.5(3) . . . . ? C26 C25 C29 C31 122.2(4) . . . . ? C24 C25 C29 C31 -60.6(5) . . . . ? C26 C25 C29 C30 -116.8(4) . . . . ? C24 C25 C29 C30 60.4(4) . . . . ? C26 C25 C29 C32 1.5(5) . . . . ? C24 C25 C29 C32 178.7(3) . . . . ? C28 C27 C33 C35 -115.2(4) . . . . ? C26 C27 C33 C35 63.4(4) . . . . ? C28 C27 C33 C36 123.2(4) . . . . ? C26 C27 C33 C36 -58.2(4) . . . . ? C28 C27 C33 C34 4.0(5) . . . . ? C26 C27 C33 C34 -177.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 25.24 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.480 _refine_diff_density_min -0.551 _refine_diff_density_rms 0.064 _database_code_depnum_ccdc_archive 'CCDC 930723' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H56 N2 O2' _chemical_formula_weight 524.81 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 'P2(1)/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.3347(6) _cell_length_b 10.3571(7) _cell_length_c 21.7602(10) _cell_angle_alpha 90.00 _cell_angle_beta 99.939(4) _cell_angle_gamma 90.00 _cell_volume 3404.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3833 _cell_measurement_theta_min 2.8949 _cell_measurement_theta_max 28.7195 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.024 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1160 _exptl_absorpt_coefficient_mu 0.062 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15052 _diffrn_reflns_av_R_equivalents 0.0296 _diffrn_reflns_av_unetI/netI 0.0460 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.90 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5990 _reflns_number_gt 4127 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5979 _refine_ls_number_parameters 359 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0867 _refine_ls_R_factor_gt 0.0600 _refine_ls_wR_factor_ref 0.1838 _refine_ls_wR_factor_gt 0.1579 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _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 N2 N 0.16339(9) 0.43449(16) 0.08947(7) 0.0425(4) Uani 1 1 d . . . N1 N 0.23673(11) 0.53098(19) 0.20897(8) 0.0565(5) Uani 1 1 d . . . O1 O 0.14931(8) 0.29175(15) 0.20846(6) 0.0512(4) Uani 1 1 d . . . H1 H 0.1597 0.3646 0.1969 0.077 Uiso 1 1 calc R . . O2 O 0.27355(9) 0.21353(16) 0.11595(6) 0.0556(4) Uani 1 1 d . . . H2 H 0.2353 0.2642 0.1228 0.083 Uiso 1 1 calc R . . C26 C 0.29665(12) 0.3785(2) -0.02856(8) 0.0459(5) Uani 1 1 d . . . H26 H 0.2641 0.4336 -0.0576 0.055 Uiso 1 1 calc R . . C23 C 0.39456(11) 0.2143(2) 0.06021(8) 0.0427(5) Uani 1 1 d . . . C8 C 0.05083(12) 0.1160(2) 0.18059(8) 0.0434(5) Uani 1 1 d . . . C21 C 0.26056(11) 0.3376(2) 0.02228(8) 0.0429(5) Uani 1 1 d . . . C20 C 0.16724(11) 0.3743(2) 0.02897(8) 0.0471(5) Uani 1 1 d . . . H20A H 0.1435 0.4339 -0.0041 0.056 Uiso 1 1 calc R . . H20B H 0.1304 0.2976 0.0243 0.056 Uiso 1 1 calc R . . C7 C 0.07961(11) 0.2400(2) 0.16785(8) 0.0407(5) Uani 1 1 d . . . C24 C 0.42629(12) 0.2574(2) 0.00756(8) 0.0465(5) Uani 1 1 d . . . H24 H 0.4820 0.2294 0.0020 0.056 Uiso 1 1 calc R . . C25 C 0.38042(12) 0.3392(2) -0.03713(9) 0.0461(5) Uani 1 1 d . . . C6 C 0.03825(11) 0.3077(2) 0.11530(8) 0.0424(5) Uani 1 1 d . . . C9 C -0.02282(12) 0.0676(2) 0.14006(9) 0.0499(5) Uani 1 1 d . . . H9 H -0.0435 -0.0139 0.1483 0.060 Uiso 1 1 calc R . . C22 C 0.30948(11) 0.2565(2) 0.06644(8) 0.0421(5) Uani 1 1 d . . . C10 C -0.06673(12) 0.1331(2) 0.08859(9) 0.0498(6) Uani 1 1 d . . . C11 C -0.03421(12) 0.2535(2) 0.07678(9) 0.0483(5) Uani 1 1 d . . . H11 H -0.0617 0.2995 0.0421 0.058 Uiso 1 1 calc R . . C5 C 0.07117(12) 0.4394(2) 0.10131(9) 0.0478(5) Uani 1 1 d . . . H5A H 0.0330 0.4747 0.0650 0.057 Uiso 1 1 calc R . . H5B H 0.0684 0.4964 0.1363 0.057 Uiso 1 1 calc R . . C27 C 0.44858(12) 0.1247(2) 0.10907(9) 0.0530(6) Uani 1 1 d . . . C12 C 0.09867(13) 0.0354(2) 0.23560(9) 0.0527(6) Uani 1 1 d . . . C4 C 0.20541(14) 0.5612(2) 0.09419(9) 0.0539(6) Uani 1 1 d . . . H4A H 0.1720 0.6179 0.0633 0.065 Uiso 1 1 calc R . . H4B H 0.2645 0.5528 0.0843 0.065 Uiso 1 1 calc R . . C31 C 0.41705(14) 0.3795(2) -0.09591(9) 0.0575(6) Uani 1 1 d . . . C3 C 0.21223(16) 0.6237(2) 0.15820(10) 0.0635(6) Uani 1 1 d . . . H3A H 0.2561 0.6920 0.1622 0.076 Uiso 1 1 calc R . . H3B H 0.1557 0.6625 0.1618 0.076 Uiso 1 1 calc R . . C16 C -0.14883(13) 0.0786(3) 0.04569(10) 0.0630(7) Uani 1 1 d . . . C13 C 0.19519(14) 0.0113(3) 0.22704(11) 0.0677(7) Uani 1 1 d . . . H13A H 0.1955 -0.0348 0.1888 0.102 Uiso 1 1 calc R . . H13B H 0.2252 -0.0388 0.2614 0.102 Uiso 1 1 calc R . . H13C H 0.2249 0.0925 0.2256 0.102 Uiso 1 1 calc R . . C30 C 0.54091(13) 0.0969(3) 0.09406(11) 0.0704(7) Uani 1 1 d . . . H30A H 0.5352 0.0520 0.0550 0.106 Uiso 1 1 calc R . . H30B H 0.5736 0.0445 0.1265 0.106 Uiso 1 1 calc R . . H30C H 0.5717 0.1768 0.0913 0.106 Uiso 1 1 calc R . . C14 C 0.09790(16) 0.1053(3) 0.29813(10) 0.0708(7) Uani 1 1 d . . . H14A H 0.1301 0.1849 0.2988 0.106 Uiso 1 1 calc R . . H14B H 0.1252 0.0513 0.3319 0.106 Uiso 1 1 calc R . . H14C H 0.0379 0.1231 0.3026 0.106 Uiso 1 1 calc R . . C28 C 0.40032(16) -0.0042(3) 0.11093(13) 0.0772(8) Uani 1 1 d . . . H28A H 0.3418 0.0112 0.1194 0.116 Uiso 1 1 calc R . . H28B H 0.4324 -0.0576 0.1432 0.116 Uiso 1 1 calc R . . H28C H 0.3965 -0.0469 0.0714 0.116 Uiso 1 1 calc R . . C33 C 0.3820(2) 0.2840(3) -0.14797(11) 0.0894(9) Uani 1 1 d . . . H33A H 0.3185 0.2866 -0.1561 0.134 Uiso 1 1 calc R . . H33B H 0.4014 0.1984 -0.1354 0.134 Uiso 1 1 calc R . . H33C H 0.4041 0.3071 -0.1852 0.134 Uiso 1 1 calc R . . C15 C 0.05461(17) -0.0967(3) 0.23988(12) 0.0777(8) Uani 1 1 d . . . H15A H -0.0057 -0.0845 0.2452 0.117 Uiso 1 1 calc R . . H15B H 0.0860 -0.1436 0.2749 0.117 Uiso 1 1 calc R . . H15C H 0.0560 -0.1445 0.2023 0.117 Uiso 1 1 calc R . . C29 C 0.46231(15) 0.1893(3) 0.17366(10) 0.0725(8) Uani 1 1 d . . . H29A H 0.4908 0.2713 0.1716 0.109 Uiso 1 1 calc R . . H29B H 0.4988 0.1351 0.2034 0.109 Uiso 1 1 calc R . . H29C H 0.4060 0.2018 0.1863 0.109 Uiso 1 1 calc R . . C19 C -0.13051(16) 0.0691(4) -0.02163(11) 0.0885(9) Uani 1 1 d . . . H19A H -0.1835 0.0426 -0.0490 0.133 Uiso 1 1 calc R . . H19B H -0.0845 0.0070 -0.0233 0.133 Uiso 1 1 calc R . . H19C H -0.1121 0.1519 -0.0346 0.133 Uiso 1 1 calc R . . C1 C 0.32842(15) 0.4874(3) 0.21232(12) 0.0765(8) Uani 1 1 d . . . H1A H 0.3350 0.4478 0.1735 0.115 Uiso 1 1 calc R . . H1B H 0.3426 0.4258 0.2455 0.115 Uiso 1 1 calc R . . H1C H 0.3676 0.5601 0.2202 0.115 Uiso 1 1 calc R . . C18 C -0.22701(14) 0.1705(3) 0.04668(12) 0.0840(9) Uani 1 1 d . . . H18A H -0.2785 0.1375 0.0199 0.126 Uiso 1 1 calc R . . H18B H -0.2128 0.2542 0.0322 0.126 Uiso 1 1 calc R . . H18C H -0.2387 0.1774 0.0885 0.126 Uiso 1 1 calc R . . C2 C 0.2260(2) 0.5892(3) 0.26843(12) 0.0994(10) Uani 1 1 d . . . H2A H 0.2636 0.6637 0.2763 0.149 Uiso 1 1 calc R . . H2B H 0.2420 0.5276 0.3014 0.149 Uiso 1 1 calc R . . H2C H 0.1654 0.6147 0.2666 0.149 Uiso 1 1 calc R . . C32 C 0.51840(16) 0.3794(4) -0.08438(12) 0.0900(10) Uani 1 1 d . . . H32A H 0.5390 0.4112 -0.1208 0.135 Uiso 1 1 calc R . . H32B H 0.5397 0.2930 -0.0757 0.135 Uiso 1 1 calc R . . H32C H 0.5401 0.4340 -0.0494 0.135 Uiso 1 1 calc R . . C34 C 0.38704(19) 0.5154(3) -0.11639(13) 0.0885(9) Uani 1 1 d . . . H34A H 0.4126 0.5397 -0.1520 0.133 Uiso 1 1 calc R . . H34B H 0.4060 0.5748 -0.0829 0.133 Uiso 1 1 calc R . . H34C H 0.3237 0.5174 -0.1272 0.133 Uiso 1 1 calc R . . C17 C -0.17452(19) -0.0553(3) 0.06627(13) 0.0978(10) Uani 1 1 d . . . H17A H -0.1854 -0.0510 0.1084 0.147 Uiso 1 1 calc R . . H17B H -0.1272 -0.1148 0.0641 0.147 Uiso 1 1 calc R . . H17C H -0.2271 -0.0840 0.0392 0.147 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 N2 0.0403(8) 0.0444(11) 0.0433(9) 0.0023(8) 0.0090(7) 0.0012(8) N1 0.0648(11) 0.0545(12) 0.0509(11) -0.0066(9) 0.0122(8) -0.0073(10) O1 0.0492(8) 0.0519(10) 0.0492(8) 0.0070(7) -0.0013(6) -0.0079(7) O2 0.0510(8) 0.0706(12) 0.0483(8) 0.0146(7) 0.0169(6) 0.0104(7) C26 0.0498(11) 0.0489(14) 0.0372(10) 0.0026(9) 0.0027(8) -0.0024(10) C23 0.0408(10) 0.0468(13) 0.0394(11) -0.0028(9) 0.0037(8) -0.0009(9) C8 0.0412(10) 0.0461(13) 0.0447(11) 0.0014(9) 0.0130(8) -0.0012(9) C21 0.0386(9) 0.0486(13) 0.0403(11) -0.0015(9) 0.0031(8) 0.0003(9) C20 0.0403(10) 0.0584(14) 0.0405(11) 0.0029(10) 0.0016(8) 0.0032(10) C7 0.0345(9) 0.0480(13) 0.0403(10) -0.0014(9) 0.0087(8) -0.0011(9) C24 0.0417(10) 0.0530(14) 0.0458(12) -0.0070(10) 0.0100(8) 0.0002(10) C25 0.0468(10) 0.0510(13) 0.0417(11) -0.0058(10) 0.0109(8) -0.0063(10) C6 0.0360(9) 0.0486(13) 0.0440(11) 0.0007(9) 0.0106(8) 0.0017(9) C9 0.0490(11) 0.0486(14) 0.0548(12) -0.0064(10) 0.0169(9) -0.0076(10) C22 0.0430(10) 0.0457(13) 0.0377(10) 0.0002(9) 0.0068(8) -0.0019(9) C10 0.0409(10) 0.0636(16) 0.0459(12) -0.0077(11) 0.0101(8) -0.0054(10) C11 0.0384(10) 0.0617(15) 0.0441(11) 0.0006(10) 0.0057(8) 0.0032(10) C5 0.0420(10) 0.0509(14) 0.0504(11) 0.0072(10) 0.0078(8) 0.0073(10) C27 0.0477(11) 0.0574(15) 0.0522(12) 0.0034(11) 0.0036(9) 0.0086(11) C12 0.0531(11) 0.0515(14) 0.0547(12) 0.0101(11) 0.0126(9) 0.0002(11) C4 0.0604(12) 0.0453(14) 0.0570(13) 0.0083(11) 0.0125(10) -0.0051(11) C31 0.0655(13) 0.0645(17) 0.0457(12) 0.0003(11) 0.0186(10) -0.0070(12) C3 0.0725(14) 0.0454(14) 0.0734(16) -0.0033(12) 0.0146(12) -0.0071(12) C16 0.0482(12) 0.0806(19) 0.0590(14) -0.0154(13) 0.0060(10) -0.0137(12) C13 0.0539(12) 0.0718(18) 0.0770(16) 0.0166(13) 0.0106(11) 0.0105(13) C30 0.0523(13) 0.079(2) 0.0788(16) 0.0074(14) 0.0077(11) 0.0208(13) C14 0.0809(16) 0.083(2) 0.0493(13) 0.0152(13) 0.0143(11) 0.0045(15) C28 0.0693(15) 0.0626(18) 0.0974(19) 0.0184(15) 0.0080(13) 0.0132(14) C33 0.126(2) 0.097(2) 0.0497(15) -0.0147(15) 0.0287(14) -0.020(2) C15 0.0801(16) 0.0579(18) 0.0951(19) 0.0252(15) 0.0152(14) -0.0050(14) C29 0.0671(14) 0.095(2) 0.0505(14) 0.0086(14) -0.0043(11) 0.0173(14) C19 0.0693(15) 0.129(3) 0.0625(16) -0.0313(17) -0.0003(12) -0.0087(17) C1 0.0676(15) 0.076(2) 0.0814(18) -0.0011(14) -0.0006(12) -0.0086(14) C18 0.0432(12) 0.120(3) 0.0863(18) -0.0178(17) 0.0038(11) -0.0058(15) C2 0.133(2) 0.103(3) 0.0670(17) -0.0249(18) 0.0308(16) -0.015(2) C32 0.0704(16) 0.130(3) 0.0773(17) 0.0122(18) 0.0355(13) -0.0132(18) C34 0.113(2) 0.080(2) 0.0810(18) 0.0234(16) 0.0408(16) -0.0050(18) C17 0.0905(19) 0.105(3) 0.092(2) -0.0256(19) -0.0015(15) -0.0421(19) _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 N2 C20 1.467(2) . ? N2 C4 1.458(3) . ? N2 C5 1.481(2) . ? N1 C3 1.463(3) . ? N1 C1 1.466(3) . ? N1 C2 1.462(3) . ? O1 C7 1.373(2) . ? O2 C22 1.367(2) . ? C26 C21 1.386(3) . ? C26 C25 1.391(3) . ? C23 C24 1.393(3) . ? C23 C22 1.405(2) . ? C23 C27 1.541(3) . ? C8 C7 1.401(3) . ? C8 C9 1.401(3) . ? C8 C12 1.538(3) . ? C21 C22 1.394(3) . ? C21 C20 1.512(2) . ? C7 C6 1.397(3) . ? C24 C25 1.386(3) . ? C25 C31 1.541(3) . ? C6 C11 1.390(3) . ? C6 C5 1.503(3) . ? C9 C10 1.381(3) . ? C10 C11 1.384(3) . ? C10 C16 1.539(3) . ? C27 C28 1.530(3) . ? C27 C30 1.534(3) . ? C27 C29 1.538(3) . ? C12 C15 1.536(3) . ? C12 C13 1.544(3) . ? C12 C14 1.543(3) . ? C4 C3 1.523(3) . ? C31 C34 1.524(4) . ? C31 C33 1.529(3) . ? C31 C32 1.531(3) . ? C16 C18 1.534(3) . ? C16 C17 1.529(4) . ? C16 C19 1.542(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 C20 N2 C4 111.09(15) . . ? C20 N2 C5 110.99(14) . . ? C4 N2 C5 112.35(16) . . ? C3 N1 C1 111.02(18) . . ? C3 N1 C2 110.1(2) . . ? C1 N1 C2 109.6(2) . . ? C21 C26 C25 121.52(18) . . ? C24 C23 C22 116.20(17) . . ? C24 C23 C27 122.55(16) . . ? C22 C23 C27 121.24(16) . . ? C7 C8 C9 116.82(18) . . ? C7 C8 C12 121.84(17) . . ? C9 C8 C12 121.33(19) . . ? C22 C21 C26 119.54(17) . . ? C22 C21 C20 119.39(16) . . ? C26 C21 C20 121.00(17) . . ? N2 C20 C21 112.25(14) . . ? O1 C7 C6 121.59(18) . . ? O1 C7 C8 117.86(17) . . ? C6 C7 C8 120.56(17) . . ? C25 C24 C23 124.46(17) . . ? C24 C25 C26 116.97(16) . . ? C24 C25 C31 122.30(17) . . ? C26 C25 C31 120.64(18) . . ? C7 C6 C11 119.57(19) . . ? C7 C6 C5 120.03(17) . . ? C11 C6 C5 120.39(18) . . ? C10 C9 C8 124.2(2) . . ? O2 C22 C21 119.85(16) . . ? O2 C22 C23 118.82(17) . . ? C21 C22 C23 121.29(16) . . ? C9 C10 C11 116.91(18) . . ? C9 C10 C16 123.0(2) . . ? C11 C10 C16 120.1(2) . . ? C6 C11 C10 121.90(19) . . ? N2 C5 C6 111.59(16) . . ? C23 C27 C28 109.80(17) . . ? C23 C27 C30 111.85(17) . . ? C28 C27 C30 108.1(2) . . ? C23 C27 C29 109.96(18) . . ? C28 C27 C29 110.2(2) . . ? C30 C27 C29 106.88(17) . . ? C8 C12 C15 112.03(18) . . ? C8 C12 C13 109.42(16) . . ? C15 C12 C13 107.7(2) . . ? C8 C12 C14 110.89(19) . . ? C15 C12 C14 107.09(18) . . ? C13 C12 C14 109.61(18) . . ? N2 C4 C3 114.00(17) . . ? C34 C31 C33 109.3(2) . . ? C34 C31 C25 110.97(18) . . ? C33 C31 C25 107.94(19) . . ? C34 C31 C32 107.2(2) . . ? C33 C31 C32 109.8(2) . . ? C25 C31 C32 111.66(18) . . ? N1 C3 C4 112.32(19) . . ? C18 C16 C17 108.5(2) . . ? C18 C16 C10 108.9(2) . . ? C17 C16 C10 112.3(2) . . ? C18 C16 C19 108.9(2) . . ? C17 C16 C19 108.6(2) . . ? C10 C16 C19 109.60(17) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.208 _refine_diff_density_min -0.267 _refine_diff_density_rms 0.072 _database_code_depnum_ccdc_archive 'CCDC 930724' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H38 N4 O6' _chemical_formula_weight 502.60 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 'P2(1)/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.5224(11) _cell_length_b 9.7342(9) _cell_length_c 19.2871(12) _cell_angle_alpha 90.00 _cell_angle_beta 105.076(7) _cell_angle_gamma 90.00 _cell_volume 2813.9(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2282 _cell_measurement_theta_min 3.0074 _cell_measurement_theta_max 28.5907 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.186 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1080 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9188 _diffrn_reflns_av_R_equivalents 0.0817 _diffrn_reflns_av_unetI/netI 0.0995 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4824 _reflns_number_gt 2465 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4824 _refine_ls_number_parameters 335 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1532 _refine_ls_R_factor_gt 0.0895 _refine_ls_wR_factor_ref 0.1624 _refine_ls_wR_factor_gt 0.1386 _refine_ls_goodness_of_fit_ref 1.434 _refine_ls_restrained_S_all 1.434 _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 N2 N 0.1543(2) 0.8236(4) 0.94543(14) 0.0525(9) Uani 1 1 d . . . N4 N 0.0969(3) 0.5277(4) 0.67579(17) 0.0642(10) Uani 1 1 d . . . N3 N -0.0838(3) 0.6578(4) 1.1289(2) 0.0722(11) Uani 1 1 d . . . N1 N 0.3243(2) 0.9433(4) 1.0111(2) 0.0763(11) Uani 1 1 d . . . O1 O 0.21558(17) 0.5989(3) 1.02510(13) 0.0652(9) Uani 1 1 d . . . H1 H 0.2167 0.6635 0.9981 0.098 Uiso 1 1 calc R . . O2 O 0.33637(17) 0.7465(4) 0.91556(14) 0.0761(10) Uani 1 1 d . . . H2 H 0.3121 0.8058 0.9340 0.114 Uiso 1 1 calc R . . O6 O 0.1239(2) 0.4377(4) 0.64240(15) 0.0893(11) Uani 1 1 d . . . O5 O 0.0197(2) 0.5699(4) 0.65958(15) 0.0845(10) Uani 1 1 d . . . O3 O -0.0751(2) 0.6271(4) 1.19257(18) 0.1056(13) Uani 1 1 d . . . O4 O -0.1503(2) 0.7117(4) 1.09074(18) 0.1029(13) Uani 1 1 d . . . C6 C 0.0672(2) 0.6805(4) 1.00911(17) 0.0496(10) Uani 1 1 d . . . C8 C 0.1414(3) 0.5423(4) 1.11512(18) 0.0517(10) Uani 1 1 d . . . C7 C 0.1417(2) 0.6082(4) 1.04990(19) 0.0519(11) Uani 1 1 d . . . C11 C -0.0069(2) 0.6943(4) 1.03451(18) 0.0543(11) Uani 1 1 d . . . H11 H -0.0562 0.7432 1.0086 0.065 Uiso 1 1 calc R . . C21 C 0.1598(3) 0.5890(5) 0.73798(18) 0.0551(11) Uani 1 1 d . . . C9 C 0.0649(3) 0.5605(4) 1.13899(19) 0.0553(11) Uani 1 1 d . . . H9 H 0.0621 0.5221 1.1825 0.066 Uiso 1 1 calc R . . C10 C -0.0069(2) 0.6346(4) 1.0992(2) 0.0525(10) Uani 1 1 d . . . C18 C 0.2761(3) 0.6932(5) 0.85675(19) 0.0583(12) Uani 1 1 d . . . C22 C 0.1314(2) 0.6929(4) 0.77406(19) 0.0543(11) Uani 1 1 d . . . H22 H 0.0734 0.7260 0.7583 0.065 Uiso 1 1 calc R . . C17 C 0.1893(3) 0.7481(5) 0.83404(19) 0.0533(11) Uani 1 1 d . . . C12 C 0.2214(3) 0.4659(5) 1.15979(19) 0.0629(12) Uani 1 1 d . . . C19 C 0.3063(3) 0.5866(5) 0.8193(2) 0.0604(12) Uani 1 1 d . . . C16 C 0.1613(3) 0.8643(5) 0.87325(18) 0.0600(12) Uani 1 1 d . . . H16A H 0.2043 0.9383 0.8780 0.072 Uiso 1 1 calc R . . H16B H 0.1040 0.8985 0.8455 0.072 Uiso 1 1 calc R . . C5 C 0.0707(2) 0.7430(5) 0.93865(17) 0.0604(12) Uani 1 1 d . . . H5A H 0.0673 0.6706 0.9035 0.072 Uiso 1 1 calc R . . H5B H 0.0195 0.8028 0.9216 0.072 Uiso 1 1 calc R . . C20 C 0.2443(3) 0.5359(5) 0.75915(18) 0.0588(12) Uani 1 1 d . . . H20 H 0.2604 0.4647 0.7329 0.071 Uiso 1 1 calc R . . C4 C 0.1609(3) 0.9423(5) 0.99363(19) 0.0639(12) Uani 1 1 d . . . H4A H 0.1175 0.9330 1.0216 0.077 Uiso 1 1 calc R . . H4B H 0.1474 1.0258 0.9654 0.077 Uiso 1 1 calc R . . C13 C 0.2492(3) 0.3477(5) 1.1149(2) 0.0759(14) Uani 1 1 d . . . H13A H 0.2002 0.2852 1.0989 0.114 Uiso 1 1 calc R . . H13B H 0.2995 0.2993 1.1442 0.114 Uiso 1 1 calc R . . H13C H 0.2650 0.3861 1.0740 0.114 Uiso 1 1 calc R . . C3 C 0.2523(3) 0.9523(7) 1.0430(3) 0.135(3) Uani 1 1 d . . . H3A H 0.2569 1.0391 1.0684 0.163 Uiso 1 1 calc R . . H3B H 0.2590 0.8798 1.0785 0.163 Uiso 1 1 calc R . . C14 C 0.3004(3) 0.5661(5) 1.1862(2) 0.0917(16) Uani 1 1 d . . . H14A H 0.3167 0.6049 1.1456 0.138 Uiso 1 1 calc R . . H14B H 0.3505 0.5173 1.2156 0.138 Uiso 1 1 calc R . . H14C H 0.2833 0.6383 1.2138 0.138 Uiso 1 1 calc R . . C15 C 0.2015(3) 0.3951(5) 1.2261(2) 0.0921(18) Uani 1 1 d . . . H15A H 0.1868 0.4635 1.2570 0.138 Uiso 1 1 calc R . . H15B H 0.2532 0.3449 1.2519 0.138 Uiso 1 1 calc R . . H15C H 0.1522 0.3331 1.2104 0.138 Uiso 1 1 calc R . . C1 C 0.3451(4) 1.0757(7) 0.9853(3) 0.140(3) Uani 1 1 d . . . H1A H 0.2910 1.1196 0.9592 0.211 Uiso 1 1 calc R . . H1B H 0.3838 1.0633 0.9543 0.211 Uiso 1 1 calc R . . H1C H 0.3743 1.1321 1.0254 0.211 Uiso 1 1 calc R . . C23 C 0.3996(3) 0.5237(6) 0.8450(3) 0.0971(18) Uani 1 1 d . . . C26 C 0.4160(3) 0.4133(7) 0.7940(3) 0.139(3) Uani 1 1 d . . . H26A H 0.3770 0.3368 0.7943 0.208 Uiso 1 1 calc R . . H26B H 0.4769 0.3832 0.8094 0.208 Uiso 1 1 calc R . . H26C H 0.4044 0.4501 0.7463 0.208 Uiso 1 1 calc R . . C25 C 0.4070(4) 0.4582(7) 0.9193(3) 0.151(3) Uani 1 1 d . . . H25A H 0.3663 0.3823 0.9142 0.227 Uiso 1 1 calc R . . H25B H 0.3925 0.5254 0.9509 0.227 Uiso 1 1 calc R . . H25C H 0.4669 0.4260 0.9391 0.227 Uiso 1 1 calc R . . C24 C 0.4711(3) 0.6357(7) 0.8512(4) 0.156(3) Uani 1 1 d . . . H24A H 0.5292 0.5960 0.8696 0.234 Uiso 1 1 calc R . . H24B H 0.4619 0.7064 0.8832 0.234 Uiso 1 1 calc R . . H24C H 0.4668 0.6745 0.8047 0.234 Uiso 1 1 calc R . . C2 C 0.4046(4) 0.8949(8) 1.0621(3) 0.162(3) Uani 1 1 d . . . H2A H 0.4242 0.9623 1.0992 0.244 Uiso 1 1 calc R . . H2B H 0.4505 0.8800 1.0379 0.244 Uiso 1 1 calc R . . H2C H 0.3920 0.8102 1.0831 0.244 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 N2 0.055(2) 0.057(2) 0.0487(18) 0.0022(17) 0.0193(15) 0.0023(18) N4 0.067(3) 0.069(3) 0.054(2) 0.006(2) 0.013(2) -0.013(2) N3 0.063(3) 0.076(3) 0.088(3) 0.002(2) 0.038(2) -0.008(2) N1 0.064(3) 0.071(3) 0.096(3) -0.010(2) 0.024(2) -0.003(2) O1 0.0580(18) 0.075(3) 0.0672(19) 0.0073(15) 0.0250(15) 0.0112(17) O2 0.0583(19) 0.091(3) 0.0742(18) -0.0250(17) 0.0094(15) 0.0055(19) O6 0.087(2) 0.110(3) 0.069(2) -0.023(2) 0.0171(17) -0.018(2) O5 0.064(2) 0.081(3) 0.089(2) 0.0046(19) -0.0141(17) -0.011(2) O3 0.097(3) 0.136(4) 0.106(2) 0.037(2) 0.066(2) 0.013(2) O4 0.050(2) 0.148(4) 0.114(3) 0.012(3) 0.0291(19) 0.018(2) C6 0.052(2) 0.051(3) 0.047(2) -0.0049(19) 0.0140(19) 0.003(2) C8 0.059(3) 0.046(3) 0.047(2) -0.004(2) 0.0082(19) 0.006(2) C7 0.051(3) 0.051(3) 0.057(2) -0.005(2) 0.020(2) 0.002(2) C11 0.047(2) 0.057(3) 0.058(2) 0.001(2) 0.0123(19) -0.001(2) C21 0.053(3) 0.069(3) 0.042(2) 0.003(2) 0.0083(19) -0.011(2) C9 0.065(3) 0.051(3) 0.053(2) -0.008(2) 0.020(2) -0.007(2) C10 0.046(2) 0.049(3) 0.067(3) -0.003(2) 0.022(2) -0.001(2) C18 0.053(3) 0.073(4) 0.049(2) -0.002(2) 0.0134(19) -0.004(2) C22 0.046(2) 0.065(3) 0.053(2) 0.007(2) 0.0150(19) 0.002(2) C17 0.054(3) 0.059(3) 0.050(2) 0.004(2) 0.021(2) 0.003(2) C12 0.072(3) 0.059(3) 0.055(2) -0.001(2) 0.014(2) 0.013(3) C19 0.051(3) 0.069(3) 0.061(2) -0.012(2) 0.013(2) 0.004(2) C16 0.064(3) 0.064(3) 0.057(2) 0.010(2) 0.025(2) 0.010(2) C5 0.058(3) 0.071(3) 0.050(2) 0.000(2) 0.0106(19) 0.002(3) C20 0.057(3) 0.070(3) 0.051(2) -0.005(2) 0.017(2) 0.000(2) C4 0.063(3) 0.068(3) 0.063(2) -0.004(2) 0.021(2) 0.009(3) C13 0.089(4) 0.060(3) 0.074(3) -0.007(2) 0.015(2) 0.029(3) C3 0.088(4) 0.165(7) 0.172(5) -0.112(5) 0.066(4) -0.047(4) C14 0.072(3) 0.099(5) 0.091(3) -0.011(3) -0.003(3) 0.015(3) C15 0.109(4) 0.102(5) 0.064(3) 0.018(3) 0.020(3) 0.041(4) C1 0.166(7) 0.104(6) 0.166(6) -0.030(5) 0.070(5) -0.055(5) C23 0.059(3) 0.108(5) 0.109(4) -0.038(4) -0.005(3) 0.024(3) C26 0.074(4) 0.160(7) 0.164(5) -0.086(5) -0.003(3) 0.045(4) C25 0.144(6) 0.143(7) 0.124(5) -0.003(5) -0.041(4) 0.059(5) C24 0.046(3) 0.166(7) 0.252(7) -0.099(6) 0.033(4) -0.013(4) C2 0.141(6) 0.167(8) 0.138(5) -0.051(5) -0.039(5) 0.038(6) _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 N2 C4 1.470(5) . ? N2 C16 1.479(4) . ? N2 C5 1.493(4) . ? N4 O5 1.227(4) . ? N4 O6 1.224(4) . ? N4 C21 1.463(5) . ? N3 O4 1.220(4) . ? N3 O3 1.237(4) . ? N3 C10 1.469(4) . ? N1 C3 1.411(5) . ? N1 C1 1.448(7) . ? N1 C2 1.451(6) . ? O1 C7 1.355(4) . ? O2 C18 1.371(4) . ? C6 C11 1.368(4) . ? C6 C7 1.406(5) . ? C6 C5 1.503(5) . ? C8 C9 1.391(5) . ? C8 C7 1.414(5) . ? C8 C12 1.511(5) . ? C11 C10 1.377(5) . ? C21 C20 1.369(5) . ? C21 C22 1.364(5) . ? C9 C10 1.380(5) . ? C18 C19 1.411(5) . ? C18 C17 1.409(5) . ? C22 C17 1.377(5) . ? C17 C16 1.487(5) . ? C12 C14 1.546(6) . ? C12 C15 1.554(5) . ? C12 C13 1.567(5) . ? C19 C20 1.392(5) . ? C19 C23 1.531(6) . ? C4 C3 1.493(6) . ? C23 C24 1.537(7) . ? C23 C26 1.522(6) . ? C23 C25 1.547(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 N2 C16 112.0(3) . . ? C4 N2 C5 112.6(3) . . ? C16 N2 C5 109.5(3) . . ? O5 N4 O6 123.4(4) . . ? O5 N4 C21 118.1(4) . . ? O6 N4 C21 118.4(4) . . ? O4 N3 O3 124.0(4) . . ? O4 N3 C10 118.5(4) . . ? O3 N3 C10 117.4(4) . . ? C3 N1 C1 111.5(5) . . ? C3 N1 C2 111.2(5) . . ? C1 N1 C2 107.1(5) . . ? C11 C6 C7 119.6(3) . . ? C11 C6 C5 121.0(4) . . ? C7 C6 C5 119.4(3) . . ? C9 C8 C7 115.9(4) . . ? C9 C8 C12 121.3(4) . . ? C7 C8 C12 122.5(3) . . ? O1 C7 C8 118.9(4) . . ? O1 C7 C6 118.9(3) . . ? C8 C7 C6 122.1(3) . . ? C6 C11 C10 118.8(4) . . ? C20 C21 C22 122.7(4) . . ? C20 C21 N4 118.3(4) . . ? C22 C21 N4 119.0(4) . . ? C10 C9 C8 121.2(4) . . ? C9 C10 C11 122.3(3) . . ? C9 C10 N3 119.0(4) . . ? C11 C10 N3 118.7(4) . . ? O2 C18 C19 117.1(4) . . ? O2 C18 C17 120.3(4) . . ? C19 C18 C17 122.5(4) . . ? C21 C22 C17 119.4(4) . . ? C22 C17 C18 118.4(4) . . ? C22 C17 C16 120.7(4) . . ? C18 C17 C16 120.8(4) . . ? C8 C12 C14 110.0(4) . . ? C8 C12 C15 112.2(3) . . ? C14 C12 C15 108.6(3) . . ? C8 C12 C13 110.5(3) . . ? C14 C12 C13 109.7(4) . . ? C15 C12 C13 105.8(4) . . ? C20 C19 C18 115.9(4) . . ? C20 C19 C23 121.2(4) . . ? C18 C19 C23 122.7(4) . . ? N2 C16 C17 112.2(3) . . ? N2 C5 C6 111.6(3) . . ? C21 C20 C19 121.0(4) . . ? N2 C4 C3 110.7(3) . . ? N1 C3 C4 116.6(4) . . ? C24 C23 C19 110.2(5) . . ? C24 C23 C26 108.2(5) . . ? C19 C23 C26 112.1(4) . . ? C24 C23 C25 110.0(5) . . ? C19 C23 C25 107.5(4) . . ? C26 C23 C25 108.8(5) . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.405 _refine_diff_density_min -0.368 _refine_diff_density_rms 0.052 _database_code_depnum_ccdc_archive 'CCDC 930725'