# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Alessandro Caselli' _publ_contact_author_email ALESSANDRO.CASELLI@UNIMI.IT _publ_section_title ; Designing new ligands: asymmetric cyclopropanation by Cu(I) complexes based on functionalised pyridine-containing macrocyclic ligands ; loop_ _publ_author_name 'Alessandro Caselli' 'Francesca Cesana' 'Emma Gallo' 'Nicola Casati' 'Piero Macchi' 'Massimo Sisti' ; G.Celentano ; 'Sergio Cenini' # Attachment 'structures.cif' data_2b _database_code_depnum_ccdc_archive 'CCDC 686134' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C39 H42 Cl Cu F3 N4 O7 S3' _chemical_formula_weight 930.94 _chemical_absolute_configuration syn #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y, x, z+3/4' 'y, -x, z+1/4' _cell_length_a 19.1493(13) _cell_length_b 19.1493(13) _cell_length_c 13.4150(9) _cell_angle_alpha 90.0000 _cell_angle_beta 90.0000 _cell_angle_gamma 90.0000 _cell_volume 4919.2(6) _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M 'P 43' _cell_formula_units_Z 4 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 7497 _cell_measurement_theta_max 19.53 _cell_measurement_theta_min 2.38 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_density_diffrn 1.257 _exptl_crystal_density_method 'not measured' _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_F_000 1924 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.682 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'SADABS - Bruker/Siemens - V2.03' _exptl_absorpt_correction_T_min 0.808 _exptl_absorpt_correction_T_max 0.966 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_measurement_device_type 'Bruker APEX2 CCD detector' _diffrn_measurement_method '\w scans' _diffrn_ambient_temperature 150(1) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_av_R_equivalents 0.0769 _diffrn_reflns_av_unetI/netI 0.0484 _diffrn_reflns_number 30014 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.06 _diffrn_reflns_theta_max 25.02 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 7107 _reflns_number_gt 5727 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_data_collection 'APEX2 (Bruker, 2007)' _computing_cell_refinement 'SAINT (Bruker, 2005)' _computing_data_reduction 'SAINT (Bruker, 2005)' _computing_structure_solution ; SIR97 - A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A. Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna, J. Appl. Cryst. (1999) 32, 115-119. ; _computing_data_correction ; SQUEEZE - P. v.d. Sluis and A. L. Spek, Acta Crystallogr., Sect A 1990, 46, 194-201. ; _computing_molecular_graphics ; ORTEP3 for Windows - L. J. Farrugia, J. Appl. Crystallogr. 1997, 30, 565. ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 7107 _refine_ls_number_parameters 482 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1032 _refine_ls_R_factor_gt 0.0914 _refine_ls_wR_factor_ref 0.2615 _refine_ls_wR_factor_gt 0.247 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.078 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.04(3) _refine_diff_density_max 1.109 _refine_diff_density_min -0.451 _refine_diff_density_rms 0.117 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F91 F 0.7239(6) 0.6966(6) 0.0280(10) 0.155(4) Uiso 1 1 d . . . F92 F 0.6807(6) 0.6326(5) -0.0977(8) 0.142(3) Uiso 1 1 d . . . F93 F 0.7307(6) 0.5774(7) 0.0280(9) 0.155(4) Uiso 1 1 d . . . C91 C 0.7214(10) 0.6397(11) -0.0245(17) 0.141(6) Uiso 1 1 d . . . S9 S 0.81069(19) 0.65138(18) -0.0851(3) 0.0950(9) Uiso 1 1 d . . . O91 O 0.7902(7) 0.7174(8) -0.1474(12) 0.158(4) Uiso 1 1 d . . . O92 O 0.8638(6) 0.6510(6) -0.0025(10) 0.137(4) Uiso 1 1 d . . . O93 O 0.8241(8) 0.5892(8) -0.1670(12) 0.169(5) Uiso 1 1 d . . . Cl81 Cl 0.7948(4) 0.3787(4) -0.2864(7) 0.120(2) Uiso 0.5 1 d P . . Cl82 Cl 0.7427(5) 0.3625(5) -0.0604(8) 0.130(3) Uiso 0.5 1 d P . . C82 C 0.7642(16) 0.4379(15) -0.109(2) 0.105(8) Uiso 0.5 1 d P . . H82A H 0.724 0.4601 -0.1391 0.126 Uiso 0.5 1 calc PR . . H82B H 0.783 0.4688 -0.0581 0.126 Uiso 0.5 1 calc PR . . C81 C 0.812(2) 0.423(2) -0.177(3) 0.143(12) Uiso 0.5 1 d P . . H81A H 0.8485 0.3972 -0.143 0.171 Uiso 0.5 1 calc PR . . H81B H 0.8328 0.4675 -0.1962 0.171 Uiso 0.5 1 calc PR . . N1 N 0.6168(4) 0.9118(3) 0.8213(6) 0.0588(19) Uani 1 1 d . . . C2 C 0.5451(4) 0.9047(4) 0.8234(6) 0.0480(18) Uani 1 1 d . . . C3 C 0.5136(5) 0.8583(4) 0.8841(8) 0.064(2) Uani 1 1 d . . . H3 H 0.4651 0.8555 0.8852 0.076 Uiso 1 1 calc R . . C4 C 0.5530(6) 0.8143(6) 0.9452(9) 0.079(3) Uani 1 1 d . . . H4 H 0.5319 0.7786 0.9814 0.095 Uiso 1 1 calc R . . C5 C 0.6235(5) 0.8251(5) 0.9504(7) 0.065(2) Uani 1 1 d . . . H5 H 0.6504 0.8005 0.9961 0.078 Uiso 1 1 calc R . . C6 C 0.6546(5) 0.8731(5) 0.8870(8) 0.064(2) Uani 1 1 d . . . C10 C 0.5022(4) 0.9510(4) 0.7567(7) 0.050(2) Uani 1 1 d . . . H10A H 0.4955 0.9281 0.693 0.06 Uiso 1 1 calc R . . H10B H 0.4566 0.9582 0.7865 0.06 Uiso 1 1 calc R . . N3 N 0.5360(3) 1.0191(3) 0.7408(6) 0.0520(16) Uani 1 1 d . . . C12 C 0.5390(4) 1.0628(4) 0.8319(6) 0.053(2) Uani 1 1 d . . . H12A H 0.5401 1.0324 0.8897 0.064 Uiso 1 1 calc R . . H12B H 0.4967 1.0905 0.8358 0.064 Uiso 1 1 calc R . . C13 C 0.6027(4) 1.1122(4) 0.8359(7) 0.056(2) Uani 1 1 d . . . H13A H 0.5998 1.1451 0.7811 0.067 Uiso 1 1 calc R . . H13B H 0.6014 1.1385 0.8976 0.067 Uiso 1 1 calc R . . C20 C 0.7294(6) 0.8786(6) 0.8905(11) 0.089(3) Uani 1 1 d . . . H20A H 0.7482 0.8416 0.8491 0.107 Uiso 1 1 calc R . . H20B H 0.7437 0.8688 0.9584 0.107 Uiso 1 1 calc R . . N4 N 0.7642(4) 0.9455(4) 0.8595(6) 0.0607(18) Uani 1 1 d . . . C22 C 0.7550(4) 1.0053(5) 0.9339(7) 0.057(2) Uani 1 1 d . . . H22A H 0.7603 0.9867 1.0008 0.068 Uiso 1 1 calc R . . H22B H 0.7923 1.0388 0.9234 0.068 Uiso 1 1 calc R . . C23 C 0.6855(4) 1.0437(5) 0.9279(6) 0.0529(19) Uani 1 1 d . . . H23A H 0.6484 1.0114 0.9452 0.063 Uiso 1 1 calc R . . H23B H 0.6854 1.0808 0.977 0.063 Uiso 1 1 calc R . . N2 N 0.6703(3) 1.0739(3) 0.8296(5) 0.0449(14) Uani 1 1 d . . . C31 C 0.7141(4) 1.1405(5) 0.6817(7) 0.057(2) Uani 1 1 d . . . C32 C 0.6984(5) 1.2059(6) 0.6537(8) 0.079(3) Uani 1 1 d . . . H32 H 0.7004 1.2414 0.701 0.095 Uiso 1 1 calc R . . C33 C 0.6787(5) 1.2230(7) 0.5534(9) 0.079(3) Uani 1 1 d . . . H33 H 0.674 1.2695 0.5346 0.095 Uiso 1 1 calc R . . C34 C 0.6676(5) 1.1744(8) 0.4896(9) 0.090(4) Uani 1 1 d . . . H34 H 0.6503 1.1856 0.4268 0.108 Uiso 1 1 calc R . . C35 C 0.6814(5) 1.1039(7) 0.5141(7) 0.072(3) Uani 1 1 d . . . C36 C 0.6644(6) 1.0463(9) 0.4484(8) 0.086(4) Uani 1 1 d . . . H36 H 0.6482 1.0554 0.3844 0.104 Uiso 1 1 calc R . . C37 C 0.6715(7) 0.9811(11) 0.4781(12) 0.115(6) Uani 1 1 d . . . H37 H 0.6534 0.9454 0.4388 0.139 Uiso 1 1 calc R . . C38 C 0.7073(6) 0.9629(7) 0.5720(9) 0.081(3) Uani 1 1 d . . . H38 H 0.7168 0.9168 0.5891 0.098 Uiso 1 1 calc R . . C39 C 0.7260(5) 1.0180(5) 0.6333(6) 0.059(2) Uani 1 1 d . . . H39 H 0.7513 1.0085 0.6909 0.07 Uiso 1 1 calc R . . C310 C 0.7083(5) 1.0873(5) 0.6123(6) 0.063(3) Uani 1 1 d . . . C111 C 0.4153(4) 1.0797(4) 0.6744(7) 0.055(2) Uani 1 1 d . . . C112 C 0.3976(4) 1.1443(4) 0.7073(7) 0.055(2) Uani 1 1 d . . . H112 H 0.4325 1.1773 0.7178 0.066 Uiso 1 1 calc R . . C113 C 0.3311(5) 1.1619(5) 0.7250(9) 0.069(3) Uani 1 1 d . . . H113 H 0.3201 1.2076 0.7422 0.083 Uiso 1 1 calc R . . C114 C 0.2782(5) 1.1120(6) 0.7179(7) 0.068(3) Uani 1 1 d . . . C115 C 0.2962(4) 1.0471(5) 0.6897(8) 0.063(2) Uani 1 1 d . . . H115 H 0.2618 1.0128 0.6885 0.076 Uiso 1 1 calc R . . C116 C 0.3643(5) 1.0287(5) 0.6620(6) 0.056(2) Uani 1 1 d . . . H116 H 0.3748 0.9848 0.6367 0.067 Uiso 1 1 calc R . . C117 C 0.2038(6) 1.1284(8) 0.7412(14) 0.116(5) Uani 1 1 d . . . H11A H 0.2001 1.1761 0.7627 0.175 Uiso 1 1 calc R . . H11B H 0.1876 1.0981 0.7932 0.175 Uiso 1 1 calc R . . H11C H 0.1758 1.1217 0.6826 0.175 Uiso 1 1 calc R . . C211 C 0.8913(5) 0.9114(5) 0.9328(8) 0.068(3) Uani 1 1 d . . . C212 C 0.8945(5) 0.8449(5) 0.9620(8) 0.065(3) Uani 1 1 d . . . H212 H 0.8739 0.8097 0.9244 0.078 Uiso 1 1 calc R . . C213 C 0.9295(5) 0.8297(5) 1.0499(8) 0.068(3) Uani 1 1 d . . . H213 H 0.9289 0.7842 1.0739 0.082 Uiso 1 1 calc R . . C214 C 0.9646(6) 0.8796(5) 1.1019(9) 0.078(3) Uani 1 1 d . . . C215 C 0.9617(6) 0.9459(5) 1.0700(9) 0.078(3) Uani 1 1 d . . . H215 H 0.9841 0.9807 1.1062 0.093 Uiso 1 1 calc R . . C216 C 0.9246(5) 0.9640(4) 0.9808(8) 0.064(2) Uani 1 1 d . . . H216 H 0.9235 1.0096 0.9571 0.077 Uiso 1 1 calc R . . C217 C 0.9984(7) 0.8600(7) 1.1999(12) 0.104(4) Uani 1 1 d . . . H21A H 0.9934 0.8107 1.2107 0.156 Uiso 1 1 calc R . . H21B H 0.9761 0.885 1.2532 0.156 Uiso 1 1 calc R . . H21C H 1.0471 0.8718 1.1979 0.156 Uiso 1 1 calc R . . C311 C 0.7297(5) 1.1205(5) 0.7883(6) 0.059(2) Uani 1 1 d . . . H311 H 0.7727 1.0928 0.7884 0.071 Uiso 1 1 calc R . . C312 C 0.7412(6) 1.1834(5) 0.8573(7) 0.067(3) Uani 1 1 d . . . H31A H 0.7512 1.1672 0.9235 0.1 Uiso 1 1 calc R . . H31B H 0.6999 1.2117 0.8583 0.1 Uiso 1 1 calc R . . H31C H 0.7799 1.2105 0.8333 0.1 Uiso 1 1 calc R . . O10 O 0.5402(3) 1.1238(3) 0.6297(4) 0.0608(15) Uani 1 1 d . . . O11 O 0.5013(4) 1.0085(4) 0.5641(5) 0.0742(17) Uani 1 1 d . . . O20 O 0.8464(3) 0.8795(3) 0.7557(5) 0.0711(18) Uani 1 1 d . . . O21 O 0.8682(3) 1.0015(3) 0.7918(5) 0.0651(16) Uani 1 1 d . . . S1 S 0.50158(11) 1.05959(12) 0.64092(16) 0.0565(6) Uani 1 1 d . . . S2 S 0.84459(12) 0.93619(11) 0.8234(2) 0.0617(6) Uani 1 1 d . . . Cu1 Cu 0.65382(6) 0.98584(5) 0.73279(7) 0.0597(4) 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 N1 0.062(4) 0.043(4) 0.071(5) 0.011(3) 0.023(4) 0.011(3) C2 0.053(5) 0.049(4) 0.042(4) -0.019(4) 0.009(4) -0.004(3) C3 0.055(5) 0.061(5) 0.075(6) 0.021(5) 0.007(5) -0.033(4) C4 0.080(7) 0.080(7) 0.077(7) 0.011(6) 0.027(5) -0.018(5) C5 0.080(6) 0.048(5) 0.067(6) -0.002(4) 0.028(5) -0.008(4) C6 0.063(5) 0.057(5) 0.071(6) -0.024(5) -0.003(5) -0.005(4) C10 0.031(4) 0.059(5) 0.061(5) -0.007(4) 0.006(3) -0.008(3) N3 0.051(4) 0.049(4) 0.056(4) -0.019(3) 0.000(3) -0.001(3) C12 0.061(5) 0.061(5) 0.037(4) 0.011(4) -0.005(4) 0.004(4) C13 0.040(4) 0.059(5) 0.068(5) 0.001(4) 0.002(4) -0.002(3) C20 0.063(6) 0.082(7) 0.123(10) 0.021(7) 0.008(6) -0.003(5) N4 0.063(4) 0.054(4) 0.066(5) -0.012(3) -0.001(4) 0.002(3) C22 0.048(4) 0.061(5) 0.061(5) 0.005(4) 0.002(4) 0.015(4) C23 0.058(5) 0.057(5) 0.044(4) 0.003(4) -0.008(4) 0.009(4) N2 0.048(4) 0.044(3) 0.042(3) 0.006(3) -0.010(3) -0.006(3) C31 0.048(5) 0.060(5) 0.065(6) 0.019(5) -0.011(4) -0.015(4) C32 0.065(6) 0.087(7) 0.085(7) 0.044(6) -0.034(5) -0.045(5) C33 0.061(6) 0.100(8) 0.075(7) 0.018(6) -0.004(5) -0.032(5) C34 0.056(6) 0.146(12) 0.067(7) 0.025(8) -0.014(5) -0.036(7) C35 0.046(5) 0.111(8) 0.058(6) 0.011(6) -0.007(4) -0.015(5) C36 0.069(7) 0.137(11) 0.053(6) 0.011(7) 0.012(5) -0.021(7) C37 0.075(8) 0.190(18) 0.081(9) -0.053(11) 0.033(7) -0.029(9) C38 0.081(7) 0.099(8) 0.064(6) -0.009(6) 0.027(6) -0.033(6) C39 0.068(5) 0.070(6) 0.038(4) -0.004(4) 0.017(4) 0.000(4) C310 0.060(5) 0.086(7) 0.042(5) 0.003(4) 0.007(4) -0.036(5) C111 0.052(5) 0.056(5) 0.057(5) -0.003(4) 0.000(4) -0.006(4) C112 0.049(5) 0.052(5) 0.065(6) -0.003(4) 0.002(4) -0.005(4) C113 0.066(6) 0.060(5) 0.082(7) 0.005(5) -0.010(5) 0.009(4) C114 0.058(5) 0.082(7) 0.064(6) 0.018(5) -0.005(4) 0.006(5) C115 0.044(5) 0.073(6) 0.073(6) 0.034(5) 0.006(4) -0.013(4) C116 0.055(5) 0.064(5) 0.049(5) 0.008(4) -0.013(4) -0.011(4) C117 0.065(7) 0.135(11) 0.149(13) 0.022(11) 0.017(8) 0.025(7) C211 0.051(5) 0.060(6) 0.093(7) -0.018(5) 0.007(5) 0.011(4) C212 0.076(6) 0.046(5) 0.074(7) 0.004(4) 0.032(5) 0.012(4) C213 0.066(6) 0.056(5) 0.083(7) 0.011(5) 0.011(5) 0.009(4) C214 0.079(7) 0.063(6) 0.092(8) -0.007(6) -0.005(6) 0.025(5) C215 0.096(7) 0.058(6) 0.080(7) -0.005(5) -0.002(6) 0.009(5) C216 0.078(6) 0.033(4) 0.082(6) -0.004(4) -0.008(5) 0.002(4) C217 0.108(9) 0.081(8) 0.123(11) 0.016(7) -0.031(8) 0.007(7) C311 0.053(5) 0.081(6) 0.042(5) 0.008(4) 0.003(4) -0.008(4) C312 0.081(6) 0.058(5) 0.061(5) 0.000(4) -0.018(5) -0.028(5) O10 0.067(4) 0.066(4) 0.050(3) 0.012(3) -0.006(3) -0.026(3) O11 0.077(4) 0.093(5) 0.053(4) -0.007(3) -0.002(3) -0.003(3) O20 0.067(4) 0.070(4) 0.076(5) -0.027(3) -0.003(3) -0.004(3) O21 0.046(3) 0.081(4) 0.068(4) -0.004(3) 0.006(3) 0.002(3) S1 0.0566(12) 0.0696(14) 0.0433(11) 0.0013(10) 0.0008(9) -0.0149(10) S2 0.0570(13) 0.0556(13) 0.0725(14) -0.0068(11) 0.0042(11) 0.0001(10) Cu1 0.0655(7) 0.0588(7) 0.0547(6) -0.0032(5) 0.0157(5) -0.0141(5) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F91 C91 1.30(2) . ? F92 C91 1.26(2) . ? F93 C91 1.40(2) . ? C91 S9 1.91(2) . ? S9 O92 1.504(13) . ? S9 O91 1.566(15) . ? S9 O93 1.640(16) . ? Cl81 C81 1.73(4) . ? Cl82 C82 1.64(3) . ? C82 C81 1.33(4) . ? N1 C6 1.359(13) . ? N1 C2 1.381(11) . ? N1 Cu1 1.980(7) . ? C2 C3 1.348(12) . ? C2 C10 1.504(12) . ? C3 C4 1.397(15) . ? C4 C5 1.367(15) . ? C5 C6 1.387(14) . ? C6 C20 1.436(14) . ? C10 N3 1.471(10) . ? N3 C12 1.483(11) . ? N3 S1 1.683(8) . ? N3 Cu1 2.346(7) . ? C12 C13 1.545(12) . ? C13 N2 1.490(10) . ? C20 N4 1.502(13) . ? N4 C22 1.530(11) . ? N4 S2 1.624(8) . ? C22 C23 1.522(11) . ? C23 N2 1.469(10) . ? N2 C311 1.550(11) . ? N2 Cu1 2.151(6) . ? C31 C32 1.342(14) . ? C31 C310 1.383(14) . ? C31 C311 1.511(12) . ? C32 C33 1.436(16) . ? C33 C34 1.281(18) . ? C34 C35 1.415(17) . ? C35 C36 1.450(18) . ? C35 C310 1.450(13) . ? C36 C37 1.32(2) . ? C37 C38 1.47(2) . ? C38 C39 1.385(14) . ? C38 Cu1 2.428(10) . ? C39 C310 1.399(14) . ? C39 Cu1 2.017(8) . ? C111 C112 1.358(12) . ? C111 C116 1.390(12) . ? C111 S1 1.755(9) . ? C112 C113 1.337(13) . ? C113 C114 1.395(14) . ? C114 C115 1.345(15) . ? C114 C117 1.492(15) . ? C115 C116 1.400(13) . ? C211 C212 1.332(13) . ? C211 C216 1.356(13) . ? C211 S2 1.783(11) . ? C212 C213 1.387(15) . ? C213 C214 1.361(15) . ? C214 C215 1.340(15) . ? C214 C217 1.512(18) . ? C215 C216 1.433(15) . ? C311 C312 1.534(13) . ? O10 S1 1.443(6) . ? O11 S1 1.421(7) . ? O20 S2 1.415(6) . ? O21 S2 1.396(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 F92 C91 F91 122.5(18) . . ? F92 C91 F93 112.3(17) . . ? F91 C91 F93 116.0(19) . . ? F92 C91 S9 103.5(14) . . ? F91 C91 S9 95.7(12) . . ? F93 C91 S9 101.5(12) . . ? O92 S9 O91 124.6(7) . . ? O92 S9 O93 112.6(8) . . ? O91 S9 O93 105.5(8) . . ? O92 S9 C91 106.9(9) . . ? O91 S9 C91 95.6(9) . . ? O93 S9 C91 110.0(9) . . ? C81 C82 Cl82 105(3) . . ? C82 C81 Cl81 124(3) . . ? C6 N1 C2 117.5(7) . . ? C6 N1 Cu1 126.1(6) . . ? C2 N1 Cu1 116.0(6) . . ? C3 C2 N1 121.5(8) . . ? C3 C2 C10 120.2(8) . . ? N1 C2 C10 118.3(7) . . ? C2 C3 C4 120.6(9) . . ? C5 C4 C3 118.2(9) . . ? C4 C5 C6 119.6(10) . . ? N1 C6 C5 122.0(9) . . ? N1 C6 C20 120.8(9) . . ? C5 C6 C20 117.2(10) . . ? N3 C10 C2 111.6(6) . . ? C10 N3 C12 113.4(7) . . ? C10 N3 S1 110.6(5) . . ? C12 N3 S1 114.2(5) . . ? C10 N3 Cu1 101.0(5) . . ? C12 N3 Cu1 98.9(5) . . ? S1 N3 Cu1 117.8(4) . . ? N3 C12 C13 113.8(7) . . ? N2 C13 C12 112.5(7) . . ? C6 C20 N4 119.7(9) . . ? C20 N4 C22 114.0(8) . . ? C20 N4 S2 114.2(6) . . ? C22 N4 S2 112.6(5) . . ? C23 C22 N4 115.3(7) . . ? N2 C23 C22 114.3(7) . . ? C23 N2 C13 108.4(7) . . ? C23 N2 C311 113.7(6) . . ? C13 N2 C311 112.0(6) . . ? C23 N2 Cu1 105.2(5) . . ? C13 N2 Cu1 107.0(5) . . ? C311 N2 Cu1 110.1(5) . . ? C32 C31 C310 118.7(9) . . ? C32 C31 C311 123.0(9) . . ? C310 C31 C311 117.8(8) . . ? C31 C32 C33 122.2(12) . . ? C34 C33 C32 120.4(12) . . ? C33 C34 C35 120.3(11) . . ? C34 C35 C36 122.9(10) . . ? C34 C35 C310 119.2(11) . . ? C36 C35 C310 117.7(11) . . ? C37 C36 C35 121.0(12) . . ? C36 C37 C38 122.0(13) . . ? C39 C38 C37 116.6(13) . . ? C39 C38 Cu1 56.2(5) . . ? C37 C38 Cu1 121.3(8) . . ? C38 C39 C310 122.7(10) . . ? C38 C39 Cu1 89.1(6) . . ? C310 C39 Cu1 104.9(6) . . ? C31 C310 C39 122.9(8) . . ? C31 C310 C35 118.6(10) . . ? C39 C310 C35 118.5(9) . . ? C112 C111 C116 120.2(8) . . ? C112 C111 S1 121.2(6) . . ? C116 C111 S1 118.5(7) . . ? C113 C112 C111 121.6(8) . . ? C112 C113 C114 120.5(9) . . ? C115 C114 C113 117.8(9) . . ? C115 C114 C117 119.9(10) . . ? C113 C114 C117 122.4(11) . . ? C114 C115 C116 123.0(9) . . ? C111 C116 C115 116.5(9) . . ? C212 C211 C216 123.2(10) . . ? C212 C211 S2 121.3(8) . . ? C216 C211 S2 115.4(7) . . ? C211 C212 C213 118.2(10) . . ? C214 C213 C212 121.8(9) . . ? C215 C214 C213 118.7(11) . . ? C215 C214 C217 122.1(11) . . ? C213 C214 C217 118.8(10) . . ? C214 C215 C216 121.0(10) . . ? C211 C216 C215 116.8(8) . . ? C31 C311 C312 113.7(8) . . ? C31 C311 N2 109.8(7) . . ? C312 C311 N2 110.0(7) . . ? O11 S1 O10 120.8(4) . . ? O11 S1 N3 105.1(4) . . ? O10 S1 N3 106.0(3) . . ? O11 S1 C111 109.5(4) . . ? O10 S1 C111 108.8(4) . . ? N3 S1 C111 105.5(4) . . ? O21 S2 O20 119.0(4) . . ? O21 S2 N4 107.4(4) . . ? O20 S2 N4 107.3(4) . . ? O21 S2 C211 109.1(4) . . ? O20 S2 C211 108.2(4) . . ? N4 S2 C211 105.0(4) . . ? N1 Cu1 C39 149.3(3) . . ? N1 Cu1 N2 104.5(3) . . ? C39 Cu1 N2 93.4(3) . . ? N1 Cu1 N3 79.8(3) . . ? C39 Cu1 N3 127.3(3) . . ? N2 Cu1 N3 84.3(2) . . ? N1 Cu1 C38 123.7(4) . . ? C39 Cu1 C38 34.8(3) . . ? N2 Cu1 C38 128.1(3) . . ? N3 Cu1 C38 119.7(4) . . ? #END #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2008-04-03 at 15:42:28 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\wingx\files\archive.dat # CIF files read : new archive24 data_5b _database_code_depnum_ccdc_archive 'CCDC 686135' _audit_creation_date 2008-04-03T15:42:28-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C41 H47 B Cl2 Cu F4 N5 O4 S2' _chemical_formula_weight 959.21 _chemical_absolute_configuration syn #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.758(5) _cell_length_b 15.027(5) _cell_length_c 15.102(5) _cell_angle_alpha 90.000 _cell_angle_beta 93.652(5) _cell_angle_gamma 90.000 _cell_volume 2210.0(15) _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' _cell_formula_units_Z 2 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 364 _cell_measurement_theta_max 17.39 _cell_measurement_theta_min 3.02 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_density_diffrn 1.441 _exptl_crystal_density_method 'not measured' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_F_000 992 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.773 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'SADABS - Bruker/Siemens - V2.03' _exptl_absorpt_correction_T_min 0.660 _exptl_absorpt_correction_T_max 0.962 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_measurement_device_type 'Bruker APEX2 CCD detector' _diffrn_measurement_method '\w scans' _diffrn_ambient_temperature 150(1) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_av_R_equivalents 0.0986 _diffrn_reflns_av_unetI/netI 0.1323 _diffrn_reflns_number 23241 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.35 _diffrn_reflns_theta_max 26.03 _diffrn_reflns_theta_full 26.03 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 8712 _reflns_number_gt 5179 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_data_collection 'APEX2 (Bruker, 2007)' _computing_cell_refinement 'SAINT (Bruker, 2005)' _computing_data_reduction 'SAINT (Bruker, 2005)' _computing_structure_solution ; SIR97 - A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A. Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna, J. Appl. Cryst. (1999) 32, 115-119. ; _computing_molecular_graphics ; ORTEP3 for Windows - L. J. Farrugia, J. Appl. Crystallogr. 1997, 30, 565. ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0374P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 8712 _refine_ls_number_parameters 532 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.1256 _refine_ls_R_factor_gt 0.0538 _refine_ls_wR_factor_ref 0.1121 _refine_ls_wR_factor_gt 0.0897 _refine_ls_goodness_of_fit_ref 0.983 _refine_ls_restrained_S_all 0.985 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.003(16) _refine_diff_density_max 0.472 _refine_diff_density_min -0.509 _refine_diff_density_rms 0.081 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 '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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C2 C -0.7405(5) -0.4315(3) -0.2949(4) 0.0205(13) Uani 1 1 d . . . C3 C -0.7552(6) -0.5235(4) -0.2837(4) 0.0296(15) Uani 1 1 d . . . H3 H -0.82 -0.5458 -0.2469 0.036 Uiso 1 1 calc R . . C4 C -0.6721(6) -0.5805(4) -0.3280(4) 0.0329(15) Uani 1 1 d . . . H4 H -0.679 -0.6417 -0.3207 0.04 Uiso 1 1 calc R . . C5 C -0.5780(6) -0.5450(4) -0.3837(4) 0.0312(15) Uani 1 1 d . . . H5 H -0.5194 -0.5819 -0.4131 0.037 Uiso 1 1 calc R . . C6 C -0.5735(5) -0.4543(4) -0.3943(4) 0.0234(13) Uani 1 1 d . . . C10 C -0.8318(5) -0.3710(4) -0.2475(4) 0.0232(14) Uani 1 1 d . . . H10A H -0.9187 -0.3661 -0.282 0.028 Uiso 1 1 calc R . . H10B H -0.8501 -0.3979 -0.1911 0.028 Uiso 1 1 calc R . . C12 C -0.6666(5) -0.2728(4) -0.1580(3) 0.0233(12) Uani 1 1 d . . . H12A H -0.6777 -0.3205 -0.1158 0.028 Uiso 1 1 calc R . . H12B H -0.678 -0.2169 -0.127 0.028 Uiso 1 1 calc R . . C13 C -0.5206(5) -0.2767(4) -0.1891(3) 0.0229(13) Uani 1 1 d . . . H13A H -0.4575 -0.26 -0.1396 0.027 Uiso 1 1 calc R . . H13B H -0.5007 -0.338 -0.204 0.027 Uiso 1 1 calc R . . C20 C -0.4783(6) -0.4158(4) -0.4596(4) 0.0342(16) Uani 1 1 d . . . H20A H -0.4023 -0.4564 -0.4659 0.041 Uiso 1 1 calc R . . H20B H -0.5277 -0.4102 -0.5172 0.041 Uiso 1 1 calc R . . C22 C -0.3414(5) -0.3303(4) -0.3442(3) 0.0235(13) Uani 1 1 d . . . H22A H -0.2461 -0.3422 -0.3547 0.028 Uiso 1 1 calc R . . H22B H -0.3744 -0.3788 -0.3088 0.028 Uiso 1 1 calc R . . C23 C -0.3500(5) -0.2443(4) -0.2927(4) 0.0263(14) Uani 1 1 d . . . H23A H -0.2891 -0.2487 -0.2395 0.032 Uiso 1 1 calc R . . H23B H -0.3165 -0.1963 -0.3285 0.032 Uiso 1 1 calc R . . C31 C -0.3987(6) -0.0867(3) -0.1746(4) 0.0237(13) Uani 1 1 d . . . C32 C -0.2640(6) -0.0733(4) -0.1947(4) 0.0247(14) Uani 1 1 d . . . H32 H -0.2393 -0.0854 -0.252 0.03 Uiso 1 1 calc R . . C33 C -0.1623(6) -0.0418(4) -0.1313(4) 0.0331(15) Uani 1 1 d . . . H33 H -0.0738 -0.0308 -0.1479 0.04 Uiso 1 1 calc R . . C34 C -0.1945(6) -0.0277(4) -0.0458(4) 0.0385(17) Uani 1 1 d . . . H34 H -0.1259 -0.0123 -0.0029 0.046 Uiso 1 1 calc R . . C35 C -0.3298(6) -0.0363(4) -0.0225(4) 0.0312(15) Uani 1 1 d . . . C36 C -0.3683(7) -0.0193(4) 0.0651(4) 0.0423(18) Uani 1 1 d . . . H36 H -0.2995 -0.0061 0.1085 0.051 Uiso 1 1 calc R . . C37 C -0.4995(7) -0.0213(5) 0.0885(4) 0.0454(18) Uani 1 1 d . . . H37 H -0.5199 -0.0103 0.1469 0.054 Uiso 1 1 calc R . . C38 C -0.6048(7) -0.0401(4) 0.0234(4) 0.0413(17) Uani 1 1 d . . . H38 H -0.6958 -0.0384 0.0382 0.05 Uiso 1 1 calc R . . C39 C -0.5748(6) -0.0608(4) -0.0614(4) 0.0321(15) Uani 1 1 d . . . H39 H -0.6461 -0.073 -0.1035 0.038 Uiso 1 1 calc R . . C92 C -0.8279(6) -0.1735(4) -0.5069(4) 0.0325(15) Uani 1 1 d . . . C93 C -0.9298(7) -0.1381(4) -0.5735(4) 0.0498(19) Uani 1 1 d . . . H93A H -1.0204 -0.1486 -0.5546 0.075 Uiso 1 1 calc R . . H93B H -0.9197 -0.1672 -0.6293 0.075 Uiso 1 1 calc R . . H93C H -0.9157 -0.0753 -0.5801 0.075 Uiso 1 1 calc R . . C111 C -0.9715(6) -0.2331(3) -0.1165(4) 0.0257(14) Uani 1 1 d . . . C112 C -0.9245(6) -0.1883(4) -0.0403(4) 0.0340(16) Uani 1 1 d . . . H112 H -0.8616 -0.1422 -0.0438 0.041 Uiso 1 1 calc R . . C113 C -0.9720(7) -0.2128(5) 0.0420(4) 0.0467(18) Uani 1 1 d . . . H113 H -0.9383 -0.1842 0.0935 0.056 Uiso 1 1 calc R . . C114 C -1.0693(7) -0.2796(6) 0.0464(4) 0.055(2) Uani 1 1 d . . . C115 C -1.1155(6) -0.3231(5) -0.0297(4) 0.0426(17) Uani 1 1 d . . . H115 H -1.1802 -0.3682 -0.0263 0.051 Uiso 1 1 calc R . . C116 C -1.0674(6) -0.3010(4) -0.1119(4) 0.0327(16) Uani 1 1 d . . . H116 H -1.0991 -0.3313 -0.1629 0.039 Uiso 1 1 calc R . . C117 C -1.1201(8) -0.3061(6) 0.1362(4) 0.085(3) Uani 1 1 d . . . H11A H -1.1583 -0.365 0.1323 0.127 Uiso 1 1 calc R . . H11B H -1.1893 -0.2649 0.1525 0.127 Uiso 1 1 calc R . . H11C H -1.0447 -0.3052 0.1802 0.127 Uiso 1 1 calc R . . C211 C -0.2064(5) -0.3402(3) -0.5375(3) 0.0227(13) Uani 1 1 d . . . C212 C -0.2202(6) -0.4045(4) -0.6038(4) 0.0291(14) Uani 1 1 d . . . H212 H -0.3027 -0.4104 -0.6377 0.035 Uiso 1 1 calc R . . C213 C -0.1110(6) -0.4595(4) -0.6191(4) 0.0342(16) Uani 1 1 d . . . H213 H -0.1202 -0.502 -0.6639 0.041 Uiso 1 1 calc R . . C214 C 0.0128(6) -0.4523(4) -0.5685(4) 0.0315(15) Uani 1 1 d . . . C215 C 0.0253(6) -0.3880(4) -0.5033(4) 0.0330(16) Uani 1 1 d . . . H215 H 0.1084 -0.3825 -0.47 0.04 Uiso 1 1 calc R . . C216 C -0.0814(6) -0.3315(4) -0.4857(4) 0.0275(14) Uani 1 1 d . . . H216 H -0.0711 -0.289 -0.441 0.033 Uiso 1 1 calc R . . C217 C 0.1309(6) -0.5145(5) -0.5844(5) 0.053(2) Uani 1 1 d . . . H21A H 0.1995 -0.483 -0.6149 0.079 Uiso 1 1 calc R . . H21B H 0.0978 -0.5639 -0.6199 0.079 Uiso 1 1 calc R . . H21C H 0.1704 -0.5359 -0.5286 0.079 Uiso 1 1 calc R . . C310 C -0.4358(6) -0.0642(4) -0.0868(4) 0.0262(14) Uani 1 1 d . . . C311 C -0.5033(5) -0.1207(3) -0.2461(4) 0.0208(13) Uani 1 1 d . . . H311 H -0.5939 -0.112 -0.223 0.025 Uiso 1 1 calc R . . C312 C -0.5026(6) -0.0668(3) -0.3305(4) 0.0276(14) Uani 1 1 d . . . H31A H -0.4201 -0.0791 -0.3597 0.041 Uiso 1 1 calc R . . H31B H -0.5063 -0.0046 -0.3165 0.041 Uiso 1 1 calc R . . H31C H -0.581 -0.0825 -0.369 0.041 Uiso 1 1 calc R . . N1 N -0.6523(5) -0.3972(3) -0.3508(3) 0.0235(11) Uani 1 1 d . . . N2 N -0.4914(4) -0.2202(3) -0.2659(3) 0.0220(11) Uani 1 1 d . . . N3 N -0.7774(4) -0.2803(3) -0.2305(3) 0.0208(11) Uani 1 1 d . . . N4 N -0.4236(4) -0.3275(3) -0.4315(3) 0.0232(10) Uani 1 1 d . . . N5 N -0.7503(5) -0.2019(3) -0.4548(3) 0.0321(12) Uani 1 1 d . . . O10 O -1.0072(4) -0.2229(2) -0.2893(2) 0.0277(10) Uani 1 1 d . . . O11 O -0.8416(4) -0.1207(2) -0.2108(3) 0.0262(10) Uani 1 1 d . . . O20 O -0.4451(3) -0.2764(3) -0.5887(2) 0.0341(10) Uani 1 1 d . . . O21 O -0.2969(4) -0.1917(2) -0.4775(3) 0.0293(10) Uani 1 1 d . . . S1 S -0.90455(15) -0.20687(9) -0.21823(10) 0.0253(3) Uani 1 1 d . . . S2 S -0.34830(14) -0.27552(10) -0.51291(9) 0.0255(3) Uani 1 1 d . . . Cu1 Cu -0.63653(7) -0.26169(4) -0.36713(5) 0.02679(18) Uani 1 1 d . . . Cl71 Cl -0.4913(2) -0.78242(16) -0.07442(14) 0.0830(7) Uani 1 1 d . . . Cl72 Cl -0.2315(2) -0.82152(16) -0.28967(16) 0.0826(7) Uani 1 1 d . . . C72 C -0.3578(9) -0.7768(8) -0.2224(6) 0.093(3) Uani 1 1 d . . . H72A H -0.337 -0.7147 -0.2101 0.111 Uiso 1 1 calc R . . H72B H -0.4469 -0.7795 -0.2547 0.111 Uiso 1 1 calc R . . C71 C -0.3633(10) -0.8218(7) -0.1442(7) 0.102(3) Uani 1 1 d . . . H71A H -0.2743 -0.8177 -0.1119 0.122 Uiso 1 1 calc R . . H71B H -0.3806 -0.8842 -0.1572 0.122 Uiso 1 1 calc R . . B1 B -0.1443(10) -0.5135(6) -0.2220(6) 0.047(5) Uiso 0.5 1 d PD . . B2 B -0.1765(11) -0.5211(6) -0.2422(7) 0.056(6) Uiso 0.5 1 d PD . . F1 F -0.2416(5) -0.4609(3) -0.1887(3) 0.0665(13) Uiso 1 1 d D . . F2 F -0.0977(4) -0.4739(2) -0.2981(2) 0.0458(10) Uiso 1 1 d D . . F31 F -0.2064(9) -0.5958(5) -0.2321(6) 0.069(3) Uiso 0.5 1 d PD . . F32 F -0.2769(9) -0.5594(6) -0.2989(6) 0.068(3) Uiso 0.5 1 d PD . . F41 F -0.0481(8) -0.5173(5) -0.1531(5) 0.058(2) Uiso 0.5 1 d PD . . F42 F -0.0889(11) -0.5901(6) -0.2163(7) 0.090(3) Uiso 0.5 1 d PD . . 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 C2 0.017(3) 0.019(3) 0.025(4) -0.004(2) -0.003(3) -0.004(3) C3 0.038(4) 0.025(3) 0.026(4) 0.002(3) 0.003(3) -0.001(3) C4 0.038(4) 0.018(3) 0.042(4) -0.010(3) -0.001(3) -0.004(3) C5 0.028(3) 0.032(4) 0.034(4) -0.005(3) 0.008(3) 0.006(3) C6 0.021(3) 0.022(3) 0.028(4) -0.006(3) 0.003(3) -0.003(3) C10 0.017(3) 0.026(3) 0.028(4) -0.002(3) 0.005(3) -0.002(3) C12 0.022(3) 0.028(3) 0.020(3) -0.003(3) 0.000(2) 0.004(3) C13 0.021(3) 0.025(3) 0.022(3) 0.002(3) -0.002(2) 0.003(3) C20 0.034(4) 0.034(4) 0.035(4) -0.014(3) 0.010(3) -0.007(3) C22 0.018(3) 0.021(3) 0.031(4) -0.003(3) 0.005(3) 0.000(3) C23 0.021(3) 0.031(4) 0.026(3) -0.006(3) -0.004(2) 0.006(3) C31 0.026(3) 0.015(3) 0.029(4) -0.005(2) 0.000(3) 0.002(3) C32 0.016(3) 0.030(3) 0.028(4) -0.005(3) 0.004(3) -0.004(3) C33 0.016(3) 0.040(4) 0.042(4) -0.006(3) -0.005(3) -0.005(3) C34 0.032(4) 0.040(4) 0.041(4) -0.022(3) -0.012(3) -0.001(3) C35 0.027(3) 0.026(3) 0.039(4) -0.014(3) -0.008(3) 0.000(3) C36 0.052(5) 0.040(4) 0.033(4) -0.019(3) -0.012(4) -0.005(4) C37 0.049(5) 0.053(5) 0.035(5) -0.021(4) 0.007(4) -0.002(4) C38 0.038(4) 0.046(4) 0.041(4) -0.018(3) 0.017(3) -0.013(3) C39 0.027(4) 0.030(4) 0.040(4) -0.006(3) 0.007(3) 0.000(3) C92 0.035(4) 0.021(3) 0.040(4) -0.003(3) -0.002(3) 0.005(3) C93 0.060(5) 0.047(5) 0.041(5) 0.009(3) -0.011(4) 0.018(4) C111 0.018(3) 0.029(3) 0.030(4) -0.003(2) 0.001(3) 0.002(2) C112 0.022(3) 0.052(4) 0.028(4) -0.006(3) 0.004(3) -0.002(3) C113 0.036(4) 0.074(5) 0.030(4) -0.014(4) 0.005(3) 0.007(4) C114 0.042(4) 0.096(7) 0.029(4) -0.002(4) 0.013(3) 0.001(5) C115 0.029(4) 0.059(4) 0.042(5) 0.001(4) 0.011(3) -0.011(4) C116 0.026(3) 0.042(4) 0.030(4) 0.001(3) -0.001(3) -0.001(3) C117 0.073(6) 0.152(9) 0.030(5) 0.017(5) 0.016(4) -0.019(6) C211 0.026(3) 0.019(3) 0.024(3) -0.004(3) 0.005(3) 0.003(3) C212 0.030(4) 0.032(3) 0.025(4) 0.001(3) 0.000(3) -0.007(3) C213 0.032(4) 0.033(4) 0.039(4) -0.015(3) 0.012(3) -0.003(3) C214 0.031(4) 0.028(4) 0.037(4) 0.000(3) 0.012(3) 0.004(3) C215 0.032(4) 0.040(4) 0.027(4) 0.007(3) 0.003(3) 0.003(3) C216 0.030(3) 0.024(3) 0.028(4) -0.005(3) 0.001(3) 0.000(3) C217 0.039(4) 0.053(4) 0.068(5) 0.001(4) 0.022(4) 0.016(4) C310 0.024(3) 0.028(3) 0.027(4) -0.002(3) 0.005(3) 0.002(3) C311 0.019(3) 0.014(3) 0.029(3) 0.001(2) -0.002(3) 0.005(2) C312 0.027(3) 0.022(3) 0.034(4) 0.001(3) 0.000(3) -0.001(3) N1 0.024(3) 0.026(3) 0.021(3) 0.004(2) 0.002(2) 0.000(2) N2 0.022(3) 0.014(2) 0.030(3) 0.002(2) 0.002(2) 0.002(2) N3 0.015(2) 0.020(3) 0.028(3) 0.000(2) 0.0050(19) 0.002(2) N4 0.023(3) 0.022(2) 0.024(3) -0.001(2) -0.001(2) -0.006(2) N5 0.032(3) 0.029(3) 0.035(3) 0.000(3) 0.001(3) 0.001(3) O10 0.021(2) 0.035(2) 0.027(2) 0.0015(17) -0.0048(18) 0.0011(18) O11 0.024(2) 0.019(2) 0.035(3) 0.0013(18) -0.0031(19) 0.0000(18) O20 0.029(2) 0.041(3) 0.031(2) 0.006(2) -0.0026(18) 0.004(2) O21 0.034(2) 0.022(2) 0.031(2) -0.0041(18) -0.0028(19) -0.0065(19) S1 0.0222(8) 0.0249(8) 0.0287(9) -0.0018(7) 0.0013(7) 0.0027(7) S2 0.0226(7) 0.0274(9) 0.0263(8) -0.0005(7) 0.0002(6) 0.0000(7) Cu1 0.0273(4) 0.0246(4) 0.0276(4) 0.0003(4) -0.0048(3) -0.0010(4) Cl71 0.0984(17) 0.0868(19) 0.0635(15) -0.0059(13) 0.0030(12) 0.0021(14) Cl72 0.0902(17) 0.0639(13) 0.0958(19) 0.0025(13) 0.0222(14) 0.0090(13) C72 0.090(6) 0.116(8) 0.071(6) 0.017(7) -0.008(5) 0.018(7) C71 0.098(8) 0.110(8) 0.098(8) 0.028(7) 0.005(6) 0.005(7) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C2 N1 1.346(6) . ? C2 C3 1.401(7) . ? C2 C10 1.489(7) . ? C3 C4 1.382(8) . ? C4 C5 1.390(8) . ? C5 C6 1.373(8) . ? C6 N1 1.350(6) . ? C6 C20 1.513(8) . ? C10 N3 1.478(6) . ? C12 N3 1.494(6) . ? C12 C13 1.530(6) . ? C13 N2 1.480(6) . ? C20 N4 1.482(7) . ? C22 N4 1.500(6) . ? C22 C23 1.513(7) . ? C23 N2 1.507(6) . ? C31 C32 1.383(7) . ? C31 C310 1.437(8) . ? C31 C311 1.526(7) . ? C32 C33 1.415(8) . ? C33 C34 1.365(8) . ? C34 C35 1.393(8) . ? C35 C36 1.421(8) . ? C35 C310 1.436(8) . ? C36 C37 1.350(8) . ? C37 C38 1.404(8) . ? C38 C39 1.368(8) . ? C39 C310 1.434(8) . ? C92 N5 1.140(7) . ? C92 C93 1.469(9) . ? C111 C112 1.384(8) . ? C111 C116 1.390(7) . ? C111 S1 1.753(6) . ? C112 C113 1.403(8) . ? C113 C114 1.386(10) . ? C114 C115 1.372(9) . ? C114 C117 1.526(9) . ? C115 C116 1.395(8) . ? C211 C212 1.392(7) . ? C211 C216 1.413(7) . ? C211 S2 1.750(5) . ? C212 C213 1.380(8) . ? C213 C214 1.391(8) . ? C214 C215 1.379(8) . ? C214 C217 1.515(8) . ? C215 C216 1.382(8) . ? C311 C312 1.510(7) . ? C311 N2 1.530(6) . ? N1 Cu1 2.058(4) . ? N2 Cu1 2.111(5) . ? N3 S1 1.680(4) . ? N4 S2 1.667(4) . ? N5 Cu1 1.898(5) . ? O10 S1 1.441(4) . ? O11 S1 1.434(4) . ? O20 S2 1.436(4) . ? O21 S2 1.445(4) . ? Cl71 C71 1.786(9) . ? Cl72 C72 1.778(9) . ? C72 C71 1.366(10) . ? B1 F1 1.357(9) . ? B1 F41 1.358(9) . ? B1 F31 1.382(9) . ? B1 F2 1.396(8) . ? B2 F2 1.374(9) . ? B2 F42 1.384(9) . ? B2 F32 1.384(9) . ? B2 F1 1.393(8) . ? F31 F42 1.159(11) . ? F31 F32 1.305(11) . ? F41 F42 1.489(12) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C2 C3 121.9(5) . . ? N1 C2 C10 119.6(5) . . ? C3 C2 C10 118.4(5) . . ? C4 C3 C2 119.0(6) . . ? C3 C4 C5 119.1(5) . . ? C6 C5 C4 118.6(5) . . ? N1 C6 C5 123.4(5) . . ? N1 C6 C20 117.9(5) . . ? C5 C6 C20 118.7(5) . . ? N3 C10 C2 115.3(4) . . ? N3 C12 C13 114.7(4) . . ? N2 C13 C12 116.6(4) . . ? N4 C20 C6 112.3(5) . . ? N4 C22 C23 112.6(5) . . ? N2 C23 C22 115.2(4) . . ? C32 C31 C310 117.9(5) . . ? C32 C31 C311 119.7(5) . . ? C310 C31 C311 122.4(5) . . ? C31 C32 C33 122.4(5) . . ? C34 C33 C32 119.9(6) . . ? C33 C34 C35 120.2(5) . . ? C34 C35 C36 122.0(5) . . ? C34 C35 C310 120.7(6) . . ? C36 C35 C310 117.3(5) . . ? C37 C36 C35 123.5(6) . . ? C36 C37 C38 118.9(6) . . ? C39 C38 C37 120.7(6) . . ? C38 C39 C310 121.4(6) . . ? N5 C92 C93 179.0(7) . . ? C112 C111 C116 120.3(6) . . ? C112 C111 S1 119.8(5) . . ? C116 C111 S1 119.9(5) . . ? C111 C112 C113 119.9(6) . . ? C114 C113 C112 119.9(6) . . ? C115 C114 C113 119.6(6) . . ? C115 C114 C117 120.8(7) . . ? C113 C114 C117 119.6(7) . . ? C114 C115 C116 121.4(6) . . ? C111 C116 C115 119.0(6) . . ? C212 C211 C216 120.2(5) . . ? C212 C211 S2 119.8(4) . . ? C216 C211 S2 119.9(4) . . ? C213 C212 C211 119.8(5) . . ? C212 C213 C214 120.9(6) . . ? C215 C214 C213 118.8(6) . . ? C215 C214 C217 120.8(6) . . ? C213 C214 C217 120.5(6) . . ? C214 C215 C216 122.3(6) . . ? C215 C216 C211 118.1(5) . . ? C39 C310 C35 117.5(5) . . ? C39 C310 C31 123.6(5) . . ? C35 C310 C31 118.6(5) . . ? C312 C311 C31 112.3(4) . . ? C312 C311 N2 110.8(4) . . ? C31 C311 N2 114.1(4) . . ? C2 N1 C6 117.9(5) . . ? C2 N1 Cu1 120.7(4) . . ? C6 N1 Cu1 121.4(4) . . ? C13 N2 C23 107.3(4) . . ? C13 N2 C311 112.7(4) . . ? C23 N2 C311 111.7(4) . . ? C13 N2 Cu1 104.1(3) . . ? C23 N2 Cu1 108.5(3) . . ? C311 N2 Cu1 112.0(3) . . ? C10 N3 C12 115.6(4) . . ? C10 N3 S1 111.4(3) . . ? C12 N3 S1 112.0(3) . . ? C20 N4 C22 113.0(4) . . ? C20 N4 S2 112.1(4) . . ? C22 N4 S2 115.2(3) . . ? C92 N5 Cu1 172.7(5) . . ? O11 S1 O10 118.9(2) . . ? O11 S1 N3 106.6(2) . . ? O10 S1 N3 106.9(2) . . ? O11 S1 C111 108.4(3) . . ? O10 S1 C111 109.6(3) . . ? N3 S1 C111 105.5(2) . . ? O20 S2 O21 119.9(3) . . ? O20 S2 N4 106.5(2) . . ? O21 S2 N4 107.1(2) . . ? O20 S2 C211 108.3(2) . . ? O21 S2 C211 107.5(2) . . ? N4 S2 C211 106.7(2) . . ? N5 Cu1 N1 120.47(19) . . ? N5 Cu1 N2 134.47(19) . . ? N1 Cu1 N2 104.91(17) . . ? C71 C72 Cl72 111.9(8) . . ? C72 C71 Cl71 114.4(7) . . ? F1 B1 F41 101.9(8) . . ? F1 B1 F31 104.5(8) . . ? F41 B1 F31 108.9(8) . . ? F1 B1 F2 109.2(7) . . ? F41 B1 F2 113.8(8) . . ? F31 B1 F2 117.1(8) . . ? F2 B2 F42 101.6(8) . . ? F2 B2 F32 103.7(8) . . ? F42 B2 F32 105.3(9) . . ? F2 B2 F1 108.3(7) . . ? F42 B2 F1 128.1(10) . . ? F32 B2 F1 107.3(8) . . ? B1 F1 B2 18.3(7) . . ? B2 F2 B1 18.2(7) . . ? F42 F31 F32 126.4(10) . . ? F42 F31 B1 59.3(7) . . ? F32 F31 B1 85.2(8) . . ? F31 F32 B2 51.6(6) . . ? B1 F41 F42 52.8(6) . . ? F31 F42 B2 54.1(7) . . ? F31 F42 F41 114.1(9) . . ? B2 F42 F41 76.5(8) . . ?