Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Lutz Gade' 'Stephane Bellemin-Laponnaz' 'Carole Foltz' 'Guido Marconi' 'Bjorn Stecker' 'Hubert Wadepohl' _publ_contact_author_name 'Lutz Gade' _publ_contact_author_address ; Anorganisch-Chemisches Institut University of Heidelberg Im Neuenheimer Feld 270 Heidelberg 69120 GERMANY ; _publ_contact_author_email LUTZ.GADE@UNI-HD.DE _publ_requested_journal 'Chemical Communications' _publ_section_title ; Exploiting C3-Symmetry in the Dynamic Coordination of a Chiral Trisoxazoline to Copper(II): Improved Enantioselectivity, and Catalyst Stability in Asymmetric Lewis Acid Catalysis ; data_ga_gm4 _database_code_depnum_ccdc_archive 'CCDC 277609' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H44 B Cu F4 N3 O6' _chemical_formula_weight 657.00 _chemical_absolute_configuration ad 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' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_int_tables_number 19 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 9.5673(5) _cell_length_b 11.3995(7) _cell_length_c 28.6673(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3126.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour green _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.396 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1380 _exptl_absorpt_coefficient_mu 0.766 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8619 _exptl_absorpt_correction_T_max 0.9627 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method omega-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18621 _diffrn_reflns_av_R_equivalents 0.0633 _diffrn_reflns_av_sigmaI/netI 0.0602 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 1.42 _diffrn_reflns_theta_max 25.03 _reflns_number_total 5535 _reflns_number_gt 4634 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 1980-2005)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0320P)^2^+1.9895P] 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 ? _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 -0.002(14) _refine_ls_number_reflns 5535 _refine_ls_number_parameters 389 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0593 _refine_ls_R_factor_gt 0.0415 _refine_ls_wR_factor_ref 0.0918 _refine_ls_wR_factor_gt 0.0847 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _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 B1 B 0.4350(7) 1.0834(5) 0.86245(19) 0.0393(15) Uani 1 1 d . . . C1 C 0.1676(4) 0.9518(3) 0.71957(13) 0.0180(9) Uani 1 1 d . . . C2 C 0.0731(4) 1.0386(4) 0.73390(13) 0.0209(9) Uani 1 1 d . . . C3 C 0.0325(4) 1.0447(4) 0.78037(14) 0.0233(9) Uani 1 1 d . . . O3 O 0.1890(3) 0.9465(2) 0.67324(8) 0.0227(7) Uani 1 1 d . . . C6 C 0.0128(5) 1.1245(4) 0.69894(14) 0.0319(10) Uani 1 1 d . . . H6A H -0.0854 1.1052 0.6930 0.048 Uiso 1 1 calc R . . H6B H 0.0656 1.1197 0.6697 0.048 Uiso 1 1 calc R . . H6C H 0.0193 1.2043 0.7115 0.048 Uiso 1 1 calc R . . C7 C -0.0693(5) 1.1353(4) 0.79672(14) 0.0329(11) Uani 1 1 d . . . H7A H -0.1058 1.1129 0.8274 0.049 Uiso 1 1 calc R . . H7B H -0.1466 1.1411 0.7744 0.049 Uiso 1 1 calc R . . H7C H -0.0221 1.2114 0.7991 0.049 Uiso 1 1 calc R . . C8 C 0.4254(4) 0.6940(3) 0.84683(13) 0.0176(9) Uani 1 1 d . . . C9 C 0.5495(5) 0.6216(4) 0.78722(13) 0.0285(10) Uani 1 1 d . . . H9A H 0.5038 0.5551 0.7711 0.034 Uiso 1 1 calc R . . H9B H 0.6505 0.6212 0.7798 0.034 Uiso 1 1 calc R . . C10 C 0.4822(4) 0.7380(3) 0.77368(13) 0.0196(9) Uani 1 1 d . . . H10 H 0.4278 0.7285 0.7441 0.024 Uiso 1 1 calc R . . C11 C 0.5857(4) 0.8392(4) 0.76885(13) 0.0228(10) Uani 1 1 d . . . H11 H 0.5297 0.9128 0.7656 0.027 Uiso 1 1 calc R . . C13 C 0.6794(4) 0.8540(4) 0.81120(15) 0.0349(10) Uani 1 1 d . . . H13A H 0.6218 0.8678 0.8389 0.052 Uiso 1 1 calc R . . H13B H 0.7419 0.9211 0.8063 0.052 Uiso 1 1 calc R . . H13C H 0.7352 0.7828 0.8157 0.052 Uiso 1 1 calc R . . C12 C 0.6731(5) 0.8264(4) 0.72442(14) 0.0301(10) Uani 1 1 d . . . H12A H 0.7371 0.8932 0.7217 0.045 Uiso 1 1 calc R . . H12B H 0.6111 0.8243 0.6972 0.045 Uiso 1 1 calc R . . H12C H 0.7272 0.7535 0.7259 0.045 Uiso 1 1 calc R . . C14 C 0.2717(4) 0.7838(3) 0.90826(12) 0.0158(8) Uani 1 1 d . . . C15 C 0.1649(4) 0.9070(3) 0.95736(13) 0.0209(9) Uani 1 1 d . . . H15A H 0.2226 0.9765 0.9650 0.025 Uiso 1 1 calc R . . H15B H 0.0911 0.8981 0.9813 0.025 Uiso 1 1 calc R . . C16 C 0.1010(4) 0.9180(3) 0.90833(13) 0.0183(9) Uani 1 1 d . . . H16 H 0.1054 1.0015 0.8976 0.022 Uiso 1 1 calc R . . C17 C -0.0480(4) 0.8722(4) 0.90397(12) 0.0209(8) Uani 1 1 d . . . H17 H -0.0707 0.8698 0.8699 0.025 Uiso 1 1 calc R . . C19 C -0.0691(5) 0.7486(4) 0.92279(14) 0.0262(10) Uani 1 1 d . . . H19A H 0.0013 0.6962 0.9093 0.039 Uiso 1 1 calc R . . H19B H -0.1627 0.7208 0.9144 0.039 Uiso 1 1 calc R . . H19C H -0.0595 0.7492 0.9568 0.039 Uiso 1 1 calc R . . C18 C -0.1497(4) 0.9587(4) 0.92650(15) 0.0306(11) Uani 1 1 d . . . H18A H -0.2459 0.9355 0.9192 0.046 Uiso 1 1 calc R . . H18B H -0.1321 1.0376 0.9144 0.046 Uiso 1 1 calc R . . H18C H -0.1363 0.9583 0.9604 0.046 Uiso 1 1 calc R . . C20 C 0.3208(4) 0.5721(3) 0.90835(13) 0.0171(9) Uani 1 1 d . . . C21 C 0.1859(5) 0.4172(3) 0.89155(13) 0.0262(11) Uani 1 1 d . . . H21A H 0.2113 0.3554 0.8688 0.031 Uiso 1 1 calc R . . H21B H 0.0835 0.4157 0.8965 0.031 Uiso 1 1 calc R . . C22 C 0.2652(5) 0.3998(3) 0.93822(12) 0.0231(9) Uani 1 1 d . . . H22 H 0.3311 0.3322 0.9348 0.028 Uiso 1 1 calc R . . C23 C 0.1705(4) 0.3775(4) 0.98034(13) 0.0258(9) Uani 1 1 d . . . H23 H 0.2324 0.3726 1.0084 0.031 Uiso 1 1 calc R . . C25 C 0.0988(5) 0.2582(4) 0.97528(16) 0.0401(13) Uani 1 1 d . . . H25A H 0.0451 0.2411 1.0036 0.060 Uiso 1 1 calc R . . H25B H 0.1697 0.1972 0.9707 0.060 Uiso 1 1 calc R . . H25C H 0.0358 0.2599 0.9483 0.060 Uiso 1 1 calc R . . C24 C 0.0662(5) 0.4762(4) 0.98938(15) 0.0334(11) Uani 1 1 d . . . H24A H 0.1163 0.5509 0.9919 0.050 Uiso 1 1 calc R . . H24B H 0.0159 0.4607 1.0185 0.050 Uiso 1 1 calc R . . H24C H -0.0006 0.4803 0.9635 0.050 Uiso 1 1 calc R . . C26 C 0.3811(4) 0.6916(3) 0.89760(13) 0.0152(8) Uani 1 1 d . . . C27 C 0.5102(4) 0.7172(4) 0.92850(14) 0.0212(9) Uani 1 1 d . . . H27A H 0.4838 0.7116 0.9614 0.032 Uiso 1 1 calc R . . H27B H 0.5449 0.7964 0.9219 0.032 Uiso 1 1 calc R . . H27C H 0.5837 0.6599 0.9217 0.032 Uiso 1 1 calc R . . Cu1 Cu 0.22860(4) 0.87213(4) 0.812432(14) 0.01660(11) Uani 1 1 d . . . F1 F 0.3762(2) 1.0382(2) 0.82133(8) 0.0285(6) Uani 1 1 d . . . F2 F 0.4619(3) 0.9914(2) 0.89312(8) 0.0364(6) Uani 1 1 d . . . F3 F 0.3403(6) 1.1561(3) 0.88265(11) 0.1150(19) Uani 1 1 d . . . F4 F 0.5535(5) 1.1413(4) 0.85154(13) 0.1137(19) Uani 1 1 d . . . N1 N 0.3852(3) 0.7596(3) 0.81358(11) 0.0165(7) Uani 1 1 d . . . N2 N 0.1988(3) 0.8445(3) 0.88008(10) 0.0153(8) Uani 1 1 d . . . N3 N 0.3480(3) 0.5096(3) 0.94364(11) 0.0202(7) Uani 1 1 d . . . O1 O 0.2363(3) 0.8802(2) 0.74491(7) 0.0181(5) Uani 1 1 d . . . O2 O 0.0740(3) 0.9755(2) 0.81329(10) 0.0282(7) Uani 1 1 d . . . O4 O 0.5259(3) 0.6162(3) 0.83811(9) 0.0242(7) Uani 1 1 d . . . O5 O 0.2515(3) 0.8006(2) 0.95435(8) 0.0196(6) Uani 1 1 d . . . O6 O 0.2316(3) 0.5322(2) 0.87540(8) 0.0245(6) Uani 1 1 d . . . C4 C 0.2938(4) 0.8654(4) 0.65586(12) 0.0215(8) Uani 1 1 d . . . H4A H 0.2724 0.7845 0.6662 0.026 Uiso 1 1 calc R . . H4B H 0.3875 0.8872 0.6677 0.026 Uiso 1 1 calc R . . C5 C 0.2903(5) 0.8730(4) 0.60330(13) 0.0394(11) Uani 1 1 d . . . H5A H 0.1987 0.8473 0.5920 0.059 Uiso 1 1 calc R . . H5B H 0.3633 0.8224 0.5902 0.059 Uiso 1 1 calc R . . H5C H 0.3068 0.9543 0.5936 0.059 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 B1 0.064(4) 0.025(3) 0.029(3) -0.003(2) -0.006(3) -0.006(3) C1 0.018(2) 0.021(2) 0.0151(19) 0.0022(17) -0.0058(18) -0.0104(17) C2 0.019(2) 0.024(2) 0.020(2) 0.0018(17) -0.0013(17) -0.0006(18) C3 0.019(2) 0.024(2) 0.027(2) 0.0051(19) 0.003(2) 0.0000(18) O3 0.0258(17) 0.0256(16) 0.0168(14) 0.0010(11) 0.0000(12) 0.0020(12) C6 0.038(3) 0.031(2) 0.026(2) 0.006(2) -0.0040(18) 0.009(2) C7 0.034(2) 0.033(3) 0.032(2) 0.007(2) 0.0020(19) 0.020(2) C8 0.014(2) 0.017(2) 0.021(2) -0.0001(17) 0.0009(17) -0.0001(17) C9 0.034(2) 0.028(2) 0.024(2) 0.003(2) 0.0137(19) 0.005(2) C10 0.021(2) 0.020(2) 0.018(2) -0.0033(17) 0.0063(17) 0.0070(17) C11 0.024(2) 0.025(2) 0.020(2) 0.0037(16) 0.0030(17) 0.0011(17) C13 0.031(2) 0.046(3) 0.027(2) -0.002(2) 0.006(2) -0.013(2) C12 0.025(2) 0.039(3) 0.026(2) 0.002(2) 0.008(2) 0.002(2) C14 0.0184(19) 0.0116(18) 0.0174(18) 0.0017(14) 0.0011(18) -0.0039(17) C15 0.023(2) 0.019(2) 0.020(2) -0.0072(16) 0.0016(18) 0.0012(17) C16 0.021(2) 0.017(2) 0.0169(19) -0.0012(15) 0.0060(17) 0.0045(16) C17 0.0181(19) 0.030(2) 0.0141(17) -0.0033(19) 0.0026(16) -0.001(2) C19 0.028(2) 0.030(3) 0.021(2) -0.0010(18) 0.0035(19) -0.005(2) C18 0.021(2) 0.041(3) 0.029(2) -0.005(2) 0.009(2) 0.003(2) C20 0.014(2) 0.018(2) 0.019(2) -0.0011(16) 0.0034(17) -0.0015(16) C21 0.040(3) 0.021(2) 0.017(2) 0.0008(16) 0.0024(19) -0.0087(19) C22 0.028(2) 0.018(2) 0.0231(19) 0.0002(15) 0.0002(19) -0.0049(19) C23 0.034(2) 0.025(2) 0.0189(19) 0.0025(19) 0.0015(17) -0.009(2) C25 0.049(3) 0.036(3) 0.035(3) 0.012(2) 0.002(2) -0.026(3) C24 0.032(3) 0.045(3) 0.023(2) -0.007(2) 0.008(2) -0.006(2) C26 0.016(2) 0.015(2) 0.0150(19) 0.0042(15) 0.0020(17) 0.0003(16) C27 0.018(2) 0.025(2) 0.021(2) 0.0061(17) -0.0044(17) -0.0028(17) Cu1 0.0165(2) 0.0197(2) 0.0137(2) 0.0034(2) 0.0020(2) 0.0031(2) F1 0.0376(14) 0.0248(13) 0.0230(13) -0.0015(10) 0.0014(11) -0.0050(11) F2 0.0457(16) 0.0331(16) 0.0305(14) 0.0051(11) -0.0058(13) -0.0121(13) F3 0.240(6) 0.060(2) 0.0453(19) -0.0193(17) 0.008(3) 0.073(3) F4 0.135(4) 0.121(4) 0.085(3) 0.055(3) -0.049(3) -0.109(3) N1 0.0183(16) 0.0183(17) 0.0128(15) -0.0007(15) 0.0025(16) -0.0004(13) N2 0.0144(18) 0.0157(18) 0.0157(15) 0.0006(12) 0.0025(13) 0.0008(13) N3 0.0229(19) 0.0163(18) 0.0213(18) 0.0058(14) -0.0008(15) -0.0005(14) O1 0.0169(14) 0.0229(14) 0.0144(11) 0.0022(11) -0.0022(11) -0.0017(14) O2 0.0292(15) 0.0326(17) 0.0228(14) 0.0131(14) 0.0055(15) 0.0114(13) O4 0.0275(16) 0.0225(16) 0.0226(14) 0.0039(13) 0.0046(12) 0.0127(15) O5 0.0231(16) 0.0226(14) 0.0133(12) -0.0013(10) -0.0010(12) 0.0018(13) O6 0.0347(17) 0.0208(14) 0.0181(13) 0.0038(10) -0.0083(14) -0.0062(14) C4 0.021(2) 0.019(2) 0.0246(19) 0.0018(17) -0.0027(17) -0.0014(19) C5 0.048(3) 0.047(3) 0.023(2) -0.002(2) 0.003(2) 0.009(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 B1 F4 1.349(7) . ? B1 F3 1.358(7) . ? B1 F2 1.393(6) . ? B1 F1 1.404(6) . ? C1 O1 1.276(4) . ? C1 O3 1.345(5) . ? C1 C2 1.401(6) . ? C2 C3 1.389(5) . ? C2 C6 1.515(6) . ? C3 O2 1.292(5) . ? C3 C7 1.496(6) . ? O3 C4 1.452(5) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 N1 1.271(5) . ? C8 O4 1.333(5) . ? C8 C26 1.516(5) . ? C9 O4 1.477(4) . ? C9 C10 1.524(6) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 N1 1.494(5) . ? C10 C11 1.526(6) . ? C10 H10 1.0000 . ? C11 C13 1.519(6) . ? C11 C12 1.531(5) . ? C11 H11 1.0000 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C14 N2 1.272(5) . ? C14 O5 1.349(4) . ? C14 C26 1.514(5) . ? C15 O5 1.471(4) . ? C15 C16 1.538(5) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 N2 1.495(5) . ? C16 C17 1.524(5) . ? C16 H16 1.0000 . ? C17 C19 1.522(6) . ? C17 C18 1.528(5) . ? C17 H17 1.0000 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C20 N3 1.265(5) . ? C20 O6 1.352(4) . ? C20 C26 1.511(5) . ? C21 O6 1.458(4) . ? C21 C22 1.551(5) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 N3 1.489(5) . ? C22 C23 1.531(5) . ? C22 H22 1.0000 . ? C23 C24 1.526(6) . ? C23 C25 1.530(6) . ? C23 H23 1.0000 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C26 C27 1.548(5) . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? Cu1 O2 1.891(3) . ? Cu1 O1 1.939(2) . ? Cu1 N1 1.973(3) . ? Cu1 N2 1.985(3) . ? Cu1 F1 2.376(2) . ? C4 C5 1.510(5) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 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 F4 B1 F3 111.2(5) . . ? F4 B1 F2 111.1(5) . . ? F3 B1 F2 108.3(4) . . ? F4 B1 F1 108.8(4) . . ? F3 B1 F1 108.3(5) . . ? F2 B1 F1 109.2(4) . . ? O1 C1 O3 117.1(3) . . ? O1 C1 C2 128.1(4) . . ? O3 C1 C2 114.8(3) . . ? C3 C2 C1 119.8(4) . . ? C3 C2 C6 119.7(4) . . ? C1 C2 C6 120.5(3) . . ? O2 C3 C2 125.8(4) . . ? O2 C3 C7 113.1(4) . . ? C2 C3 C7 121.1(4) . . ? C1 O3 C4 118.2(3) . . ? C2 C6 H6A 109.5 . . ? C2 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C2 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C3 C7 H7A 109.5 . . ? C3 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C3 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N1 C8 O4 118.0(3) . . ? N1 C8 C26 130.3(4) . . ? O4 C8 C26 111.7(3) . . ? O4 C9 C10 102.9(3) . . ? O4 C9 H9A 111.2 . . ? C10 C9 H9A 111.2 . . ? O4 C9 H9B 111.2 . . ? C10 C9 H9B 111.2 . . ? H9A C9 H9B 109.1 . . ? N1 C10 C9 102.2(3) . . ? N1 C10 C11 110.3(3) . . ? C9 C10 C11 114.0(3) . . ? N1 C10 H10 110.0 . . ? C9 C10 H10 110.0 . . ? C11 C10 H10 110.0 . . ? C13 C11 C10 113.2(3) . . ? C13 C11 C12 110.7(3) . . ? C10 C11 C12 111.0(3) . . ? C13 C11 H11 107.2 . . ? C10 C11 H11 107.2 . . ? C12 C11 H11 107.2 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N2 C14 O5 117.8(3) . . ? N2 C14 C26 128.9(3) . . ? O5 C14 C26 113.3(3) . . ? O5 C15 C16 103.8(3) . . ? O5 C15 H15A 111.0 . . ? C16 C15 H15A 111.0 . . ? O5 C15 H15B 111.0 . . ? C16 C15 H15B 111.0 . . ? H15A C15 H15B 109.0 . . ? N2 C16 C17 110.4(3) . . ? N2 C16 C15 101.5(3) . . ? C17 C16 C15 114.7(3) . . ? N2 C16 H16 109.9 . . ? C17 C16 H16 109.9 . . ? C15 C16 H16 109.9 . . ? C19 C17 C16 114.4(3) . . ? C19 C17 C18 111.3(3) . . ? C16 C17 C18 109.8(3) . . ? C19 C17 H17 107.0 . . ? C16 C17 H17 107.0 . . ? C18 C17 H17 107.0 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N3 C20 O6 119.9(3) . . ? N3 C20 C26 126.4(4) . . ? O6 C20 C26 113.7(3) . . ? O6 C21 C22 104.0(3) . . ? O6 C21 H21A 111.0 . . ? C22 C21 H21A 111.0 . . ? O6 C21 H21B 111.0 . . ? C22 C21 H21B 111.0 . . ? H21A C21 H21B 109.0 . . ? N3 C22 C23 111.8(3) . . ? N3 C22 C21 104.1(3) . . ? C23 C22 C21 114.3(3) . . ? N3 C22 H22 108.8 . . ? C23 C22 H22 108.8 . . ? C21 C22 H22 108.8 . . ? C24 C23 C22 113.5(3) . . ? C24 C23 C25 112.2(4) . . ? C22 C23 C25 109.8(3) . . ? C24 C23 H23 107.0 . . ? C22 C23 H23 107.0 . . ? C25 C23 H23 107.0 . . ? C23 C25 H25A 109.5 . . ? C23 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C23 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C20 C26 C14 108.7(3) . . ? C20 C26 C8 108.6(3) . . ? C14 C26 C8 112.0(3) . . ? C20 C26 C27 111.0(3) . . ? C14 C26 C27 107.8(3) . . ? C8 C26 C27 108.9(3) . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? O2 Cu1 O1 90.77(12) . . ? O2 Cu1 N1 177.36(13) . . ? O1 Cu1 N1 91.05(12) . . ? O2 Cu1 N2 88.51(12) . . ? O1 Cu1 N2 171.12(12) . . ? N1 Cu1 N2 89.40(12) . . ? O2 Cu1 F1 88.08(11) . . ? O1 Cu1 F1 92.69(9) . . ? N1 Cu1 F1 93.74(10) . . ? N2 Cu1 F1 96.13(10) . . ? B1 F1 Cu1 128.4(3) . . ? C8 N1 C10 106.8(3) . . ? C8 N1 Cu1 128.7(3) . . ? C10 N1 Cu1 124.5(2) . . ? C14 N2 C16 107.7(3) . . ? C14 N2 Cu1 128.9(3) . . ? C16 N2 Cu1 122.0(2) . . ? C20 N3 C22 106.3(3) . . ? C1 O1 Cu1 125.4(2) . . ? C3 O2 Cu1 127.7(3) . . ? C8 O4 C9 105.5(3) . . ? C14 O5 C15 104.8(3) . . ? C20 O6 C21 105.7(3) . . ? O3 C4 C5 106.9(3) . . ? O3 C4 H4A 110.3 . . ? C5 C4 H4A 110.3 . . ? O3 C4 H4B 110.3 . . ? C5 C4 H4B 110.3 . . ? H4A C4 H4B 108.6 . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 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 O1 C1 C2 C3 -7.7(6) . . . . ? O3 C1 C2 C3 173.7(4) . . . . ? O1 C1 C2 C6 173.4(4) . . . . ? O3 C1 C2 C6 -5.2(6) . . . . ? C1 C2 C3 O2 -0.2(7) . . . . ? C6 C2 C3 O2 178.7(4) . . . . ? C1 C2 C3 C7 -179.3(4) . . . . ? C6 C2 C3 C7 -0.4(6) . . . . ? O1 C1 O3 C4 -3.6(5) . . . . ? C2 C1 O3 C4 175.1(3) . . . . ? O4 C9 C10 N1 -20.7(4) . . . . ? O4 C9 C10 C11 98.3(4) . . . . ? N1 C10 C11 C13 62.3(4) . . . . ? C9 C10 C11 C13 -52.0(5) . . . . ? N1 C10 C11 C12 -172.5(3) . . . . ? C9 C10 C11 C12 73.1(4) . . . . ? O5 C15 C16 N2 -20.0(4) . . . . ? O5 C15 C16 C17 99.1(4) . . . . ? N2 C16 C17 C19 62.9(4) . . . . ? C15 C16 C17 C19 -51.1(4) . . . . ? N2 C16 C17 C18 -171.1(3) . . . . ? C15 C16 C17 C18 74.9(4) . . . . ? O6 C21 C22 N3 0.4(4) . . . . ? O6 C21 C22 C23 122.7(3) . . . . ? N3 C22 C23 C24 59.1(4) . . . . ? C21 C22 C23 C24 -58.9(4) . . . . ? N3 C22 C23 C25 -174.5(3) . . . . ? C21 C22 C23 C25 67.6(5) . . . . ? N3 C20 C26 C14 -103.8(4) . . . . ? O6 C20 C26 C14 77.3(4) . . . . ? N3 C20 C26 C8 134.2(4) . . . . ? O6 C20 C26 C8 -44.8(4) . . . . ? N3 C20 C26 C27 14.6(5) . . . . ? O6 C20 C26 C27 -164.4(3) . . . . ? N2 C14 C26 C20 -106.5(4) . . . . ? O5 C14 C26 C20 73.1(4) . . . . ? N2 C14 C26 C8 13.4(6) . . . . ? O5 C14 C26 C8 -167.0(3) . . . . ? N2 C14 C26 C27 133.1(4) . . . . ? O5 C14 C26 C27 -47.3(4) . . . . ? N1 C8 C26 C20 120.0(4) . . . . ? O4 C8 C26 C20 -62.7(4) . . . . ? N1 C8 C26 C14 0.0(6) . . . . ? O4 C8 C26 C14 177.3(3) . . . . ? N1 C8 C26 C27 -119.1(5) . . . . ? O4 C8 C26 C27 58.2(4) . . . . ? F4 B1 F1 Cu1 153.6(3) . . . . ? F3 B1 F1 Cu1 -85.4(5) . . . . ? F2 B1 F1 Cu1 32.3(6) . . . . ? O2 Cu1 F1 B1 97.0(4) . . . . ? O1 Cu1 F1 B1 -172.4(4) . . . . ? N1 Cu1 F1 B1 -81.1(4) . . . . ? N2 Cu1 F1 B1 8.7(4) . . . . ? O4 C8 N1 C10 -7.4(5) . . . . ? C26 C8 N1 C10 169.7(4) . . . . ? O4 C8 N1 Cu1 173.5(2) . . . . ? C26 C8 N1 Cu1 -9.3(6) . . . . ? C9 C10 N1 C8 17.7(4) . . . . ? C11 C10 N1 C8 -103.9(4) . . . . ? C9 C10 N1 Cu1 -163.2(3) . . . . ? C11 C10 N1 Cu1 75.2(4) . . . . ? O2 Cu1 N1 C8 -31(3) . . . . ? O1 Cu1 N1 C8 -164.8(3) . . . . ? N2 Cu1 N1 C8 6.3(4) . . . . ? F1 Cu1 N1 C8 102.4(3) . . . . ? O2 Cu1 N1 C10 150(3) . . . . ? O1 Cu1 N1 C10 16.3(3) . . . . ? N2 Cu1 N1 C10 -172.6(3) . . . . ? F1 Cu1 N1 C10 -76.5(3) . . . . ? O5 C14 N2 C16 -2.6(5) . . . . ? C26 C14 N2 C16 177.0(4) . . . . ? O5 C14 N2 Cu1 164.1(2) . . . . ? C26 C14 N2 Cu1 -16.3(6) . . . . ? C17 C16 N2 C14 -107.7(4) . . . . ? C15 C16 N2 C14 14.4(4) . . . . ? C17 C16 N2 Cu1 84.5(3) . . . . ? C15 C16 N2 Cu1 -153.4(2) . . . . ? O2 Cu1 N2 C14 -175.9(3) . . . . ? O1 Cu1 N2 C14 98.7(8) . . . . ? N1 Cu1 N2 C14 5.7(3) . . . . ? F1 Cu1 N2 C14 -88.0(3) . . . . ? O2 Cu1 N2 C16 -10.9(3) . . . . ? O1 Cu1 N2 C16 -96.3(8) . . . . ? N1 Cu1 N2 C16 170.7(3) . . . . ? F1 Cu1 N2 C16 77.0(3) . . . . ? O6 C20 N3 C22 -0.3(5) . . . . ? C26 C20 N3 C22 -179.2(3) . . . . ? C23 C22 N3 C20 -124.0(4) . . . . ? C21 C22 N3 C20 -0.1(4) . . . . ? O3 C1 O1 Cu1 178.3(2) . . . . ? C2 C1 O1 Cu1 -0.2(5) . . . . ? O2 Cu1 O1 C1 10.2(3) . . . . ? N1 Cu1 O1 C1 -171.7(3) . . . . ? N2 Cu1 O1 C1 95.4(8) . . . . ? F1 Cu1 O1 C1 -77.9(3) . . . . ? C2 C3 O2 Cu1 15.6(6) . . . . ? C7 C3 O2 Cu1 -165.3(3) . . . . ? O1 Cu1 O2 C3 -17.6(4) . . . . ? N1 Cu1 O2 C3 -151(3) . . . . ? N2 Cu1 O2 C3 171.2(4) . . . . ? F1 Cu1 O2 C3 75.0(3) . . . . ? N1 C8 O4 C9 -6.9(5) . . . . ? C26 C8 O4 C9 175.4(3) . . . . ? C10 C9 O4 C8 17.4(4) . . . . ? N2 C14 O5 C15 -11.2(4) . . . . ? C26 C14 O5 C15 169.1(3) . . . . ? C16 C15 O5 C14 19.1(4) . . . . ? N3 C20 O6 C21 0.6(5) . . . . ? C26 C20 O6 C21 179.6(3) . . . . ? C22 C21 O6 C20 -0.5(4) . . . . ? C1 O3 C4 C5 177.1(4) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.396 _refine_diff_density_min -0.396 _refine_diff_density_rms 0.065 #===END data_ga_gm7 _database_code_depnum_ccdc_archive 'CCDC 277610' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H44 Cl Cu N3 O10' _chemical_formula_weight 669.64 _chemical_absolute_configuration ad 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 orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_int_tables_number 19 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 9.5398(8) _cell_length_b 11.5517(9) _cell_length_c 28.674(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3159.9(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour green _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.408 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1412 _exptl_absorpt_coefficient_mu 0.833 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8188 _exptl_absorpt_correction_T_max 0.9595 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method omega-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18461 _diffrn_reflns_av_R_equivalents 0.0703 _diffrn_reflns_av_sigmaI/netI 0.0715 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 25.03 _reflns_number_total 5589 _reflns_number_gt 4503 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'DIRDIF (Beurskens, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 1980-2005)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0571P)^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 ? _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 -0.007(16) _refine_ls_number_reflns 5589 _refine_ls_number_parameters 389 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0678 _refine_ls_R_factor_gt 0.0497 _refine_ls_wR_factor_ref 0.1125 _refine_ls_wR_factor_gt 0.1059 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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 0.1637(6) 0.9535(4) 0.71938(15) 0.0258(12) Uani 1 1 d . . . C2 C 0.0709(6) 1.0391(4) 0.73496(16) 0.0259(12) Uani 1 1 d . . . C3 C 0.0279(5) 1.0420(4) 0.78042(17) 0.0259(12) Uani 1 1 d . . . C4 C 0.2896(6) 0.8715(4) 0.65633(14) 0.0265(11) Uani 1 1 d . . . H4A H 0.2656 0.7916 0.6659 0.032 Uiso 1 1 calc R . . H4B H 0.3834 0.8907 0.6689 0.032 Uiso 1 1 calc R . . C5 C 0.2902(7) 0.8808(5) 0.60362(16) 0.0458(15) Uani 1 1 d . . . H5A H 0.1979 0.8592 0.5915 0.069 Uiso 1 1 calc R . . H5B H 0.3614 0.8286 0.5908 0.069 Uiso 1 1 calc R . . H5C H 0.3118 0.9606 0.5945 0.069 Uiso 1 1 calc R . . C6 C 0.0127(6) 1.1260(5) 0.70036(17) 0.0387(14) Uani 1 1 d . . . H6A H -0.0833 1.1041 0.6919 0.058 Uiso 1 1 calc R . . H6B H 0.0714 1.1269 0.6723 0.058 Uiso 1 1 calc R . . H6C H 0.0122 1.2033 0.7145 0.058 Uiso 1 1 calc R . . C7 C -0.0753(6) 1.1306(5) 0.79805(19) 0.0423(15) Uani 1 1 d . . . H7A H -0.1052 1.1098 0.8296 0.063 Uiso 1 1 calc R . . H7B H -0.1570 1.1327 0.7774 0.063 Uiso 1 1 calc R . . H7C H -0.0306 1.2070 0.7986 0.063 Uiso 1 1 calc R . . C8 C 0.4224(5) 0.6924(4) 0.84590(16) 0.0192(11) Uani 1 1 d . . . C9 C 0.5430(6) 0.6197(4) 0.78618(15) 0.0266(12) Uani 1 1 d . . . H9A H 0.4944 0.5553 0.7701 0.032 Uiso 1 1 calc R . . H9B H 0.6441 0.6168 0.7785 0.032 Uiso 1 1 calc R . . C10 C 0.4796(5) 0.7364(4) 0.77279(16) 0.0206(11) Uani 1 1 d . . . H10 H 0.4245 0.7285 0.7433 0.025 Uiso 1 1 calc R . . C11 C 0.5839(6) 0.8359(4) 0.76822(15) 0.0241(12) Uani 1 1 d . . . H11 H 0.5286 0.9092 0.7656 0.029 Uiso 1 1 calc R . . C12 C 0.6707(6) 0.8236(4) 0.72306(17) 0.0309(13) Uani 1 1 d . . . H12A H 0.7244 0.7513 0.7241 0.046 Uiso 1 1 calc R . . H12B H 0.7353 0.8892 0.7203 0.046 Uiso 1 1 calc R . . H12C H 0.6076 0.8224 0.6961 0.046 Uiso 1 1 calc R . . C13 C 0.6789(6) 0.8477(4) 0.81015(17) 0.0332(12) Uani 1 1 d . . . H13A H 0.6221 0.8609 0.8381 0.050 Uiso 1 1 calc R . . H13B H 0.7426 0.9132 0.8055 0.050 Uiso 1 1 calc R . . H13C H 0.7336 0.7765 0.8140 0.050 Uiso 1 1 calc R . . C14 C 0.2689(5) 0.7806(3) 0.90759(14) 0.0155(9) Uani 1 1 d . . . C15 C 0.1648(6) 0.9029(4) 0.95699(15) 0.0237(12) Uani 1 1 d . . . H15A H 0.2233 0.9714 0.9642 0.028 Uiso 1 1 calc R . . H15B H 0.0921 0.8944 0.9814 0.028 Uiso 1 1 calc R . . C16 C 0.0979(5) 0.9132(4) 0.90806(15) 0.0186(10) Uani 1 1 d . . . H16 H 0.1017 0.9955 0.8973 0.022 Uiso 1 1 calc R . . C17 C -0.0508(5) 0.8682(4) 0.90413(15) 0.0240(10) Uani 1 1 d . . . H17 H -0.0750 0.8658 0.8702 0.029 Uiso 1 1 calc R . . C18 C -0.0714(6) 0.7463(4) 0.92344(16) 0.0268(12) Uani 1 1 d . . . H18A H -0.0003 0.6946 0.9103 0.040 Uiso 1 1 calc R . . H18B H -0.1650 0.7182 0.9150 0.040 Uiso 1 1 calc R . . H18C H -0.0622 0.7479 0.9575 0.040 Uiso 1 1 calc R . . C19 C -0.1512(6) 0.9538(5) 0.92740(17) 0.0305(13) Uani 1 1 d . . . H19A H -0.1373 0.9520 0.9613 0.046 Uiso 1 1 calc R . . H19B H -0.2481 0.9323 0.9201 0.046 Uiso 1 1 calc R . . H19C H -0.1324 1.0321 0.9158 0.046 Uiso 1 1 calc R . . C20 C 0.3184(5) 0.5717(4) 0.90781(14) 0.0155(10) Uani 1 1 d . . . C21 C 0.1854(6) 0.4179(4) 0.89162(15) 0.0254(13) Uani 1 1 d . . . H21A H 0.2125 0.3570 0.8691 0.030 Uiso 1 1 calc R . . H21B H 0.0827 0.4149 0.8964 0.030 Uiso 1 1 calc R . . C22 C 0.2635(6) 0.4023(3) 0.93803(14) 0.0215(11) Uani 1 1 d . . . H22 H 0.3296 0.3356 0.9349 0.026 Uiso 1 1 calc R . . C23 C 0.1689(6) 0.3809(4) 0.98042(15) 0.0258(11) Uani 1 1 d . . . H23 H 0.2308 0.3777 1.0085 0.031 Uiso 1 1 calc R . . C24 C 0.0632(6) 0.4785(5) 0.98827(17) 0.0377(14) Uani 1 1 d . . . H24A H 0.1130 0.5526 0.9902 0.057 Uiso 1 1 calc R . . H24B H 0.0122 0.4647 1.0174 0.057 Uiso 1 1 calc R . . H24C H -0.0032 0.4808 0.9622 0.057 Uiso 1 1 calc R . . C25 C 0.0986(7) 0.2637(5) 0.9759(2) 0.0479(18) Uani 1 1 d . . . H25A H 0.0436 0.2477 1.0040 0.072 Uiso 1 1 calc R . . H25B H 0.1702 0.2036 0.9720 0.072 Uiso 1 1 calc R . . H25C H 0.0365 0.2639 0.9486 0.072 Uiso 1 1 calc R . . C26 C 0.3786(5) 0.6909(4) 0.89647(14) 0.0156(10) Uani 1 1 d . . . C27 C 0.5105(5) 0.7141(4) 0.92690(17) 0.0234(12) Uani 1 1 d . . . H27A H 0.5802 0.6534 0.9213 0.035 Uiso 1 1 calc R . . H27B H 0.4840 0.7140 0.9599 0.035 Uiso 1 1 calc R . . H27C H 0.5504 0.7896 0.9187 0.035 Uiso 1 1 calc R . . Cl1 Cl 0.43444(16) 1.08111(10) 0.86309(4) 0.0317(3) Uani 1 1 d . . . Cu1 Cu 0.22621(6) 0.87025(5) 0.812094(17) 0.01725(14) Uani 1 1 d . . . N1 N 0.3823(4) 0.7591(3) 0.81284(13) 0.0178(8) Uani 1 1 d . . . N2 N 0.1959(4) 0.8413(3) 0.87962(12) 0.0162(9) Uani 1 1 d . . . N3 N 0.3475(5) 0.5112(3) 0.94308(12) 0.0228(10) Uani 1 1 d . . . O1 O 0.2346(3) 0.8799(3) 0.74465(9) 0.0212(7) Uani 1 1 d . . . O2 O 0.0690(3) 0.9708(3) 0.81289(11) 0.0272(8) Uani 1 1 d . . . O3 O 0.1876(4) 0.9509(3) 0.67373(10) 0.0313(9) Uani 1 1 d . . . O4 O 0.5205(4) 0.6143(3) 0.83655(11) 0.0261(8) Uani 1 1 d . . . O5 O 0.2507(4) 0.7982(2) 0.95348(9) 0.0202(8) Uani 1 1 d . . . O6 O 0.2283(4) 0.5317(2) 0.87502(9) 0.0253(8) Uani 1 1 d . . . O7 O 0.3752(4) 1.0367(3) 0.82052(10) 0.0276(8) Uani 1 1 d . . . O8 O 0.5588(6) 1.1421(5) 0.85190(16) 0.092(2) Uani 1 1 d . . . O9 O 0.3336(7) 1.1542(4) 0.88407(14) 0.086(2) Uani 1 1 d . . . O10 O 0.4645(4) 0.9864(3) 0.89443(11) 0.0327(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.033(3) 0.034(3) 0.011(2) 0.008(2) -0.010(2) -0.019(3) C2 0.020(3) 0.031(3) 0.027(3) 0.005(2) -0.003(2) -0.003(2) C3 0.017(3) 0.027(3) 0.034(3) 0.008(2) 0.000(2) -0.006(2) C4 0.030(3) 0.025(2) 0.025(2) 0.000(2) -0.004(2) -0.003(3) C5 0.061(4) 0.050(3) 0.027(3) 0.000(3) 0.007(3) 0.010(4) C6 0.039(4) 0.047(3) 0.030(3) 0.014(3) -0.005(2) 0.008(3) C7 0.040(4) 0.037(3) 0.051(3) 0.015(3) -0.001(3) 0.019(3) C8 0.013(3) 0.018(3) 0.026(3) -0.001(2) 0.005(2) -0.002(2) C9 0.037(3) 0.020(3) 0.023(2) 0.005(2) 0.015(2) 0.006(3) C10 0.024(3) 0.017(2) 0.021(2) -0.0034(19) 0.010(2) -0.001(2) C11 0.029(3) 0.024(3) 0.019(2) 0.0041(19) 0.011(2) 0.001(2) C12 0.029(3) 0.036(3) 0.028(3) 0.003(2) 0.013(2) 0.002(3) C13 0.030(3) 0.041(3) 0.029(3) 0.004(3) 0.003(2) -0.010(2) C14 0.014(3) 0.017(2) 0.016(2) 0.0009(17) -0.004(2) -0.011(2) C15 0.027(3) 0.025(3) 0.019(2) -0.0092(19) 0.004(2) -0.001(2) C16 0.017(3) 0.017(2) 0.022(2) 0.0042(18) 0.0043(19) 0.005(2) C17 0.020(3) 0.036(3) 0.016(2) 0.000(2) 0.0028(19) 0.002(3) C18 0.022(3) 0.036(3) 0.022(3) -0.006(2) 0.005(2) -0.010(3) C19 0.017(3) 0.044(3) 0.030(3) -0.005(2) 0.007(2) 0.003(3) C20 0.012(3) 0.016(2) 0.019(2) 0.0017(19) 0.0048(18) 0.000(2) C21 0.040(4) 0.018(2) 0.018(2) -0.0046(19) 0.008(2) -0.010(2) C22 0.030(3) 0.012(2) 0.022(2) 0.0001(16) 0.002(2) 0.000(2) C23 0.036(3) 0.027(3) 0.015(2) 0.006(2) 0.0019(19) -0.010(3) C24 0.030(4) 0.058(4) 0.025(3) -0.012(3) 0.010(2) -0.003(3) C25 0.064(5) 0.041(4) 0.038(3) 0.015(3) 0.002(3) -0.028(3) C26 0.018(3) 0.017(2) 0.013(2) 0.0003(17) -0.0004(19) 0.000(2) C27 0.018(3) 0.028(3) 0.024(3) 0.007(2) -0.002(2) -0.004(2) Cl1 0.0504(10) 0.0199(6) 0.0249(6) -0.0018(5) -0.0032(6) -0.0103(6) Cu1 0.0157(3) 0.0227(3) 0.0133(2) 0.0038(2) 0.0016(2) 0.0006(3) N1 0.018(2) 0.0200(19) 0.0149(18) -0.0027(17) 0.0039(18) -0.0056(16) N2 0.015(2) 0.018(2) 0.0155(19) -0.0022(15) 0.0031(15) -0.0054(16) N3 0.024(3) 0.027(2) 0.018(2) 0.0089(18) 0.0002(17) -0.0022(19) O1 0.0181(19) 0.0261(17) 0.0195(15) 0.0012(14) -0.0021(13) -0.0011(17) O2 0.025(2) 0.0312(18) 0.0258(17) 0.0107(16) 0.0024(17) 0.0089(16) O3 0.039(3) 0.036(2) 0.0183(17) -0.0008(14) -0.0036(15) 0.0071(18) O4 0.028(2) 0.0223(19) 0.0275(18) 0.0071(14) 0.0066(14) 0.0083(18) O5 0.022(2) 0.0229(17) 0.0157(15) 0.0008(12) 0.0004(14) 0.0018(15) O6 0.038(2) 0.0208(16) 0.0175(16) 0.0044(12) -0.0081(16) -0.0092(17) O7 0.041(2) 0.0234(17) 0.0189(18) 0.0016(14) -0.0038(15) -0.0066(16) O8 0.091(5) 0.113(5) 0.072(3) 0.048(3) -0.034(3) -0.079(4) O9 0.173(6) 0.046(3) 0.040(2) -0.014(2) 0.019(3) 0.055(3) O10 0.040(3) 0.033(2) 0.0251(19) 0.0079(15) -0.0053(17) -0.0088(18) _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 O1 1.306(6) . ? C1 O3 1.329(5) . ? C1 C2 1.400(7) . ? C2 C3 1.367(7) . ? C2 C6 1.517(7) . ? C3 O2 1.302(6) . ? C3 C7 1.508(7) . ? C4 O3 1.427(6) . ? C4 C5 1.515(6) . ? C8 N1 1.280(6) . ? C8 O4 1.328(6) . ? C8 C26 1.509(6) . ? C9 O4 1.462(5) . ? C9 C10 1.527(7) . ? C10 N1 1.499(6) . ? C10 C11 1.526(7) . ? C11 C13 1.512(7) . ? C11 C12 1.544(6) . ? C14 N2 1.273(6) . ? C14 O5 1.343(5) . ? C14 C26 1.506(6) . ? C15 O5 1.464(5) . ? C15 C16 1.546(6) . ? C16 N2 1.493(6) . ? C16 C17 1.515(7) . ? C17 C18 1.526(7) . ? C17 C19 1.530(7) . ? C20 N3 1.260(5) . ? C20 O6 1.355(5) . ? C20 C26 1.527(6) . ? C21 O6 1.456(5) . ? C21 C22 1.536(6) . ? C22 N3 1.499(6) . ? C22 C23 1.534(6) . ? C23 C25 1.517(7) . ? C23 C24 1.529(8) . ? C26 C27 1.555(7) . ? Cl1 O9 1.414(5) . ? Cl1 O8 1.417(5) . ? Cl1 O7 1.440(3) . ? Cl1 O10 1.445(4) . ? Cu1 O2 1.897(3) . ? Cu1 O1 1.939(3) . ? Cu1 N1 1.966(4) . ? Cu1 N2 1.986(3) . ? Cu1 O7 2.403(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 O1 C1 O3 116.3(5) . . ? O1 C1 C2 127.6(4) . . ? O3 C1 C2 116.0(4) . . ? C3 C2 C1 120.7(4) . . ? C3 C2 C6 119.9(5) . . ? C1 C2 C6 119.4(4) . . ? O2 C3 C2 125.2(5) . . ? O2 C3 C7 112.7(4) . . ? C2 C3 C7 122.1(4) . . ? O3 C4 C5 107.8(4) . . ? N1 C8 O4 118.0(4) . . ? N1 C8 C26 129.5(4) . . ? O4 C8 C26 112.4(4) . . ? O4 C9 C10 103.2(4) . . ? N1 C10 C11 109.8(3) . . ? N1 C10 C9 101.9(3) . . ? C11 C10 C9 115.4(4) . . ? C13 C11 C10 113.0(4) . . ? C13 C11 C12 110.7(5) . . ? C10 C11 C12 110.6(4) . . ? N2 C14 O5 117.6(4) . . ? N2 C14 C26 128.7(4) . . ? O5 C14 C26 113.7(4) . . ? O5 C15 C16 103.5(3) . . ? N2 C16 C17 110.8(4) . . ? N2 C16 C15 101.2(4) . . ? C17 C16 C15 115.3(4) . . ? C16 C17 C18 114.2(4) . . ? C16 C17 C19 109.4(4) . . ? C18 C17 C19 111.0(4) . . ? N3 C20 O6 120.5(4) . . ? N3 C20 C26 126.0(4) . . ? O6 C20 C26 113.5(3) . . ? O6 C21 C22 104.7(4) . . ? N3 C22 C23 111.9(3) . . ? N3 C22 C21 104.1(3) . . ? C23 C22 C21 114.9(4) . . ? C25 C23 C24 112.3(5) . . ? C25 C23 C22 109.6(4) . . ? C24 C23 C22 112.7(4) . . ? C14 C26 C8 112.8(4) . . ? C14 C26 C20 108.3(4) . . ? C8 C26 C20 108.6(4) . . ? C14 C26 C27 108.9(4) . . ? C8 C26 C27 108.3(4) . . ? C20 C26 C27 109.9(4) . . ? O9 Cl1 O8 111.6(4) . . ? O9 Cl1 O7 107.9(3) . . ? O8 Cl1 O7 108.3(2) . . ? O9 Cl1 O10 108.8(2) . . ? O8 Cl1 O10 110.6(3) . . ? O7 Cl1 O10 109.6(2) . . ? O2 Cu1 O1 90.54(14) . . ? O2 Cu1 N1 176.71(15) . . ? O1 Cu1 N1 90.98(14) . . ? O2 Cu1 N2 88.64(15) . . ? O1 Cu1 N2 171.17(15) . . ? N1 Cu1 N2 89.41(15) . . ? O2 Cu1 O7 88.66(14) . . ? O1 Cu1 O7 91.71(12) . . ? N1 Cu1 O7 94.21(14) . . ? N2 Cu1 O7 97.05(13) . . ? C8 N1 C10 106.1(4) . . ? C8 N1 Cu1 128.9(3) . . ? C10 N1 Cu1 125.0(3) . . ? C14 N2 C16 107.8(4) . . ? C14 N2 Cu1 128.8(3) . . ? C16 N2 Cu1 122.0(3) . . ? C20 N3 C22 105.6(4) . . ? C1 O1 Cu1 124.7(3) . . ? C3 O2 Cu1 128.0(3) . . ? C1 O3 C4 118.4(4) . . ? C8 O4 C9 105.9(4) . . ? C14 O5 C15 105.4(3) . . ? C20 O6 C21 105.0(3) . . ? Cl1 O7 Cu1 127.07(18) . . ? 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 O1 C1 C2 C3 -10.4(8) . . . . ? O3 C1 C2 C3 173.3(5) . . . . ? O1 C1 C2 C6 172.4(5) . . . . ? O3 C1 C2 C6 -3.9(7) . . . . ? C1 C2 C3 O2 1.7(8) . . . . ? C6 C2 C3 O2 178.9(5) . . . . ? C1 C2 C3 C7 -178.1(5) . . . . ? C6 C2 C3 C7 -0.9(8) . . . . ? O4 C9 C10 N1 -21.3(5) . . . . ? O4 C9 C10 C11 97.5(4) . . . . ? N1 C10 C11 C13 63.6(5) . . . . ? C9 C10 C11 C13 -50.9(5) . . . . ? N1 C10 C11 C12 -171.7(4) . . . . ? C9 C10 C11 C12 73.9(5) . . . . ? O5 C15 C16 N2 -20.7(4) . . . . ? O5 C15 C16 C17 98.9(4) . . . . ? N2 C16 C17 C18 63.5(5) . . . . ? C15 C16 C17 C18 -50.6(5) . . . . ? N2 C16 C17 C19 -171.5(4) . . . . ? C15 C16 C17 C19 74.4(5) . . . . ? O6 C21 C22 N3 -0.9(5) . . . . ? O6 C21 C22 C23 121.9(4) . . . . ? N3 C22 C23 C25 -173.9(4) . . . . ? C21 C22 C23 C25 67.6(5) . . . . ? N3 C22 C23 C24 60.3(5) . . . . ? C21 C22 C23 C24 -58.2(5) . . . . ? N2 C14 C26 C8 12.3(7) . . . . ? O5 C14 C26 C8 -166.2(4) . . . . ? N2 C14 C26 C20 -108.0(5) . . . . ? O5 C14 C26 C20 73.5(5) . . . . ? N2 C14 C26 C27 132.5(5) . . . . ? O5 C14 C26 C27 -46.0(5) . . . . ? N1 C8 C26 C14 1.7(7) . . . . ? O4 C8 C26 C14 179.0(4) . . . . ? N1 C8 C26 C20 121.8(5) . . . . ? O4 C8 C26 C20 -60.9(5) . . . . ? N1 C8 C26 C27 -118.9(5) . . . . ? O4 C8 C26 C27 58.4(5) . . . . ? N3 C20 C26 C14 -103.6(5) . . . . ? O6 C20 C26 C14 77.8(4) . . . . ? N3 C20 C26 C8 133.6(5) . . . . ? O6 C20 C26 C8 -45.0(5) . . . . ? N3 C20 C26 C27 15.3(6) . . . . ? O6 C20 C26 C27 -163.3(4) . . . . ? O4 C8 N1 C10 -7.8(6) . . . . ? C26 C8 N1 C10 169.4(5) . . . . ? O4 C8 N1 Cu1 172.0(3) . . . . ? C26 C8 N1 Cu1 -10.8(7) . . . . ? C11 C10 N1 C8 -104.6(4) . . . . ? C9 C10 N1 C8 18.1(5) . . . . ? C11 C10 N1 Cu1 75.5(5) . . . . ? C9 C10 N1 Cu1 -161.7(3) . . . . ? O2 Cu1 N1 C8 -47(3) . . . . ? O1 Cu1 N1 C8 -164.5(4) . . . . ? N2 Cu1 N1 C8 6.7(4) . . . . ? O7 Cu1 N1 C8 103.7(4) . . . . ? O2 Cu1 N1 C10 133(3) . . . . ? O1 Cu1 N1 C10 15.4(3) . . . . ? N2 Cu1 N1 C10 -173.5(3) . . . . ? O7 Cu1 N1 C10 -76.4(3) . . . . ? O5 C14 N2 C16 -4.1(5) . . . . ? C26 C14 N2 C16 177.5(4) . . . . ? O5 C14 N2 Cu1 162.5(3) . . . . ? C26 C14 N2 Cu1 -16.0(7) . . . . ? C17 C16 N2 C14 -107.1(4) . . . . ? C15 C16 N2 C14 15.6(5) . . . . ? C17 C16 N2 Cu1 85.2(4) . . . . ? C15 C16 N2 Cu1 -152.0(3) . . . . ? O2 Cu1 N2 C14 -176.8(4) . . . . ? O1 Cu1 N2 C14 98.5(10) . . . . ? N1 Cu1 N2 C14 5.9(4) . . . . ? O7 Cu1 N2 C14 -88.3(4) . . . . ? O2 Cu1 N2 C16 -11.9(3) . . . . ? O1 Cu1 N2 C16 -96.6(10) . . . . ? N1 Cu1 N2 C16 170.8(3) . . . . ? O7 Cu1 N2 C16 76.6(3) . . . . ? O6 C20 N3 C22 -0.9(6) . . . . ? C26 C20 N3 C22 -179.4(4) . . . . ? C23 C22 N3 C20 -123.6(4) . . . . ? C21 C22 N3 C20 1.0(5) . . . . ? O3 C1 O1 Cu1 177.0(3) . . . . ? C2 C1 O1 Cu1 0.7(7) . . . . ? O2 Cu1 O1 C1 11.0(4) . . . . ? N1 Cu1 O1 C1 -171.9(4) . . . . ? N2 Cu1 O1 C1 95.6(10) . . . . ? O7 Cu1 O1 C1 -77.6(4) . . . . ? C2 C3 O2 Cu1 16.3(7) . . . . ? C7 C3 O2 Cu1 -163.9(3) . . . . ? O1 Cu1 O2 C3 -19.5(4) . . . . ? N1 Cu1 O2 C3 -137(3) . . . . ? N2 Cu1 O2 C3 169.3(4) . . . . ? O7 Cu1 O2 C3 72.2(4) . . . . ? O1 C1 O3 C4 -1.5(6) . . . . ? C2 C1 O3 C4 175.2(4) . . . . ? C5 C4 O3 C1 176.6(5) . . . . ? N1 C8 O4 C9 -6.9(6) . . . . ? C26 C8 O4 C9 175.4(4) . . . . ? C10 C9 O4 C8 17.9(5) . . . . ? N2 C14 O5 C15 -10.4(5) . . . . ? C26 C14 O5 C15 168.3(4) . . . . ? C16 C15 O5 C14 19.2(5) . . . . ? N3 C20 O6 C21 0.3(6) . . . . ? C26 C20 O6 C21 178.9(4) . . . . ? C22 C21 O6 C20 0.5(5) . . . . ? O9 Cl1 O7 Cu1 -85.0(3) . . . . ? O8 Cl1 O7 Cu1 154.1(3) . . . . ? O10 Cl1 O7 Cu1 33.4(3) . . . . ? O2 Cu1 O7 Cl1 96.9(3) . . . . ? O1 Cu1 O7 Cl1 -172.6(3) . . . . ? N1 Cu1 O7 Cl1 -81.5(3) . . . . ? N2 Cu1 O7 Cl1 8.4(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.500 _refine_diff_density_min -0.432 _refine_diff_density_rms 0.074