# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_jtn101 _database_code_depnum_ccdc_archive 'CCDC 886191' #TrackingRef 'web_deposit_cif_file_0_JonT.Njardarson_1339529666.1_Cuhfacac3NEt4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H20 N +, C15 H3 Cu F18 O6 -' _chemical_formula_sum 'C23 H23 Cu F18 N O6' _chemical_formula_weight 814.96 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.2817(7) _cell_length_b 10.9413(7) _cell_length_c 15.5048(11) _cell_angle_alpha 88.673(3) _cell_angle_beta 82.244(2) _cell_angle_gamma 67.515(2) _cell_volume 1596.10(19) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 9893 _cell_measurement_theta_min 2.16 _cell_measurement_theta_max 25.30 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.98 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.696 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 814 _exptl_absorpt_coefficient_mu 0.827 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.4994 _exptl_absorpt_correction_T_max 0.8681 _exptl_absorpt_process_details 'SADABS; Sheldrick, 1996' _exptl_special_details ; In the complex, five of the six -CF3 groups exhibit significant libration, consistent with 'free' rotation of the C-C bond. This is a common problem, and is generally reduced in significance by low temperature data collection. In this structure the temperature could not be lowered below 200K and so the -CF3 groups have been refined using a two-part disorder model, with their geometry restrained to be approximately similar to the non-disordered group (defined by C5, F4, F5, F6). In the cation, two of the four ethyl groups were also refined using a two-part disorder model. ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube with Miracol optics' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Kappa APEXII DUO CCD diffractometer' _diffrn_measurement_method 'thin-slice \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 52748 _diffrn_reflns_av_R_equivalents 0.0272 _diffrn_reflns_av_sigmaI/netI 0.0130 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 25.43 _reflns_number_total 5885 _reflns_number_gt 5088 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 (Bruker, 2007)' _computing_cell_refinement 'SAINT (Bruker, 2007)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement SHELXTL _computing_molecular_graphics 'ORTEP3 for Windows (Farrugia, 1997)' _computing_publication_material 'SHELXTL and local programs' _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^)+(0.0559P)^2^+1.0159P] 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 5885 _refine_ls_number_parameters 620 _refine_ls_number_restraints 1243 _refine_ls_R_factor_all 0.0433 _refine_ls_R_factor_gt 0.0356 _refine_ls_wR_factor_ref 0.1067 _refine_ls_wR_factor_gt 0.0985 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.109 _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 Cu Cu 0.86462(3) 0.72119(3) 0.725541(18) 0.03975(11) Uani 1 1 d . . . C6 C 0.7657(3) 0.5992(3) 0.49066(18) 0.0531(6) Uani 1 1 d DU . . F7 F 0.6410(2) 0.6073(2) 0.47432(15) 0.0917(7) Uani 1 1 d DU . . F8 F 0.8254(3) 0.6383(2) 0.42061(12) 0.0963(7) Uani 1 1 d DU . . F9 F 0.8453(2) 0.47315(18) 0.49692(13) 0.0767(5) Uani 1 1 d DU . . C1 C 1.2797(3) 0.7507(3) 0.6293(2) 0.0606(7) Uani 0.60(3) 1 d PDU A 1 F1 F 1.2280(14) 0.8641(9) 0.5907(8) 0.092(3) Uani 0.60(3) 1 d PDU A 1 F2 F 1.3548(12) 0.7724(11) 0.6861(6) 0.085(2) Uani 0.60(3) 1 d PDU A 1 F3 F 1.3669(16) 0.6632(13) 0.5734(11) 0.124(4) Uani 0.60(3) 1 d PDU A 1 C1' C 1.2797(3) 0.7507(3) 0.6293(2) 0.0606(7) Uani 0.40(3) 1 d PDU A 2 F1' F 1.229(2) 0.8756(10) 0.6121(15) 0.100(4) Uani 0.40(3) 1 d PDU A 2 F2' F 1.3942(18) 0.724(3) 0.6635(15) 0.118(6) Uani 0.40(3) 1 d PDU A 2 F3' F 1.322(3) 0.689(2) 0.5518(9) 0.101(5) Uani 0.40(3) 1 d PDU A 2 C5 C 1.1996(4) 0.4200(4) 0.8267(3) 0.0777(10) Uani 0.53(3) 1 d PDU A 1 F4 F 1.1092(12) 0.4266(13) 0.8972(6) 0.100(3) Uani 0.53(3) 1 d PDU A 1 F5 F 1.3137(19) 0.416(2) 0.8542(16) 0.140(5) Uani 0.53(3) 1 d PDU A 1 F6 F 1.2185(15) 0.3066(9) 0.7868(9) 0.105(3) Uani 0.53(3) 1 d PDU A 1 C5' C 1.1996(4) 0.4200(4) 0.8267(3) 0.0777(10) Uani 0.47(3) 1 d PDU A 2 F4' F 1.151(3) 0.440(2) 0.9078(8) 0.163(7) Uani 0.47(3) 1 d PDU A 2 F5' F 1.3410(9) 0.3867(15) 0.8220(14) 0.097(4) Uani 0.47(3) 1 d PDU A 2 F6' F 1.1929(14) 0.3122(11) 0.7995(13) 0.113(4) Uani 0.47(3) 1 d PDU A 2 C10 C 0.5121(4) 1.0318(3) 0.6471(2) 0.0720(9) Uani 0.61(3) 1 d PDU B 1 F10 F 0.4468(17) 1.0579(17) 0.7307(5) 0.144(5) Uani 0.61(3) 1 d PDU B 1 F11 F 0.5407(15) 1.1302(11) 0.6194(14) 0.133(4) Uani 0.61(3) 1 d PDU B 1 F12 F 0.4075(14) 1.023(2) 0.6109(10) 0.083(4) Uani 0.61(3) 1 d PDU B 1 C10' C 0.5121(4) 1.0318(3) 0.6471(2) 0.0720(9) Uani 0.39(3) 1 d PDU B 2 F10' F 0.4876(15) 1.0944(13) 0.7197(8) 0.084(3) Uani 0.39(3) 1 d PDU B 2 F11' F 0.5677(17) 1.1081(12) 0.5899(7) 0.072(3) Uani 0.39(3) 1 d PDU B 2 F12' F 0.403(2) 1.043(3) 0.6067(13) 0.067(3) Uani 0.39(3) 1 d PDU B 2 C11 C 0.4947(4) 0.6876(4) 0.8954(3) 0.0839(10) Uani 0.56(4) 1 d PDU C 1 F13 F 0.501(2) 0.640(2) 0.9761(6) 0.130(4) Uani 0.56(4) 1 d PDU C 1 F14 F 0.3809(13) 0.7895(12) 0.8955(17) 0.153(5) Uani 0.56(4) 1 d PDU C 1 F15 F 0.4873(14) 0.5936(12) 0.8478(9) 0.093(3) Uani 0.56(4) 1 d PDU C 1 C11' C 0.4947(4) 0.6876(4) 0.8954(3) 0.0839(10) Uani 0.44(4) 1 d PDU C 2 F13' F 0.454(2) 0.701(3) 0.9791(8) 0.153(6) Uani 0.44(4) 1 d PDU C 2 F14' F 0.3882(14) 0.7875(15) 0.8638(15) 0.119(5) Uani 0.44(4) 1 d PDU C 2 F15' F 0.491(2) 0.5801(16) 0.8667(18) 0.125(5) Uani 0.44(4) 1 d PDU C 2 C15 C 0.8175(6) 0.8887(5) 0.9787(2) 0.1007(14) Uani 0.58(2) 1 d PDU C 1 F16 F 0.9461(12) 0.862(2) 0.9787(8) 0.194(6) Uani 0.58(2) 1 d PDU C 1 F17 F 0.7499(16) 0.8830(17) 1.0548(6) 0.120(4) Uani 0.58(2) 1 d PDU C 1 F18 F 0.756(2) 1.0226(8) 0.9602(5) 0.165(5) Uani 0.58(2) 1 d PDU C 1 C15' C 0.8175(6) 0.8887(5) 0.9787(2) 0.1007(14) Uani 0.42(2) 1 d PDU C 2 F16' F 0.9444(13) 0.7964(11) 1.0053(9) 0.118(4) Uani 0.42(2) 1 d PDU C 2 F17' F 0.728(2) 0.913(2) 1.0523(10) 0.116(5) Uani 0.42(2) 1 d PDU C 2 F18' F 0.8528(18) 0.9861(14) 0.9596(7) 0.111(4) Uani 0.42(2) 1 d PDU C 2 O1 O 1.04367(18) 0.76697(18) 0.65937(12) 0.0492(4) Uani 1 1 d . A . O2 O 1.00473(18) 0.55542(17) 0.76367(13) 0.0496(4) Uani 1 1 d . A . O3 O 0.85283(17) 0.63320(18) 0.61620(11) 0.0484(4) Uani 1 1 d . . . O4 O 0.7199(2) 0.89097(18) 0.69585(13) 0.0534(5) Uani 1 1 d . B . O5 O 0.6866(2) 0.6714(2) 0.79099(13) 0.0582(5) Uani 1 1 d . C . O6 O 0.8669(2) 0.80831(19) 0.83675(13) 0.0550(5) Uani 1 1 d . C . C2 C 1.1650(3) 0.7065(3) 0.67715(17) 0.0453(6) Uani 1 1 d U . . C3 C 1.2127(3) 0.6023(3) 0.7326(2) 0.0524(6) Uani 1 1 d U A . H3 H 1.3074 0.5749 0.7453 0.063 Uiso 1 1 calc R . . C4 C 1.1308(3) 0.5367(3) 0.77006(19) 0.0499(6) Uani 1 1 d U . . C7 C 0.7564(2) 0.6831(3) 0.57050(16) 0.0418(5) Uani 1 1 d U . . C8 C 0.6452(3) 0.8055(3) 0.58122(17) 0.0472(6) Uani 1 1 d U B . H8 H 0.5726 0.8262 0.5450 0.057 Uiso 1 1 calc R . . C9 C 0.6365(3) 0.8981(3) 0.64239(18) 0.0465(6) Uani 1 1 d U . . C12 C 0.6301(3) 0.7133(3) 0.86490(18) 0.0540(6) Uani 1 1 d U . . C13 C 0.6715(4) 0.7810(3) 0.92357(19) 0.0636(8) Uani 1 1 d U C . H13 H 0.6180 0.8018 0.9800 0.076 Uiso 1 1 calc R . . C14 C 0.7839(4) 0.8197(3) 0.90579(18) 0.0564(7) Uani 1 1 d U . . N_2 N 0.8632(2) 0.2235(2) 0.73108(14) 0.0473(5) Uani 1 1 d DU . . C16_2 C 0.856(3) 0.3242(18) 0.7994(10) 0.045(4) Uani 0.35(6) 1 d PDU D 1 H16A_2 H 0.8202 0.4142 0.7758 0.054 Uiso 0.35(6) 1 calc PR D 1 H16B_2 H 0.9526 0.3053 0.8142 0.054 Uiso 0.35(6) 1 calc PR D 1 C17_2 C 0.758(3) 0.318(3) 0.8811(15) 0.074(6) Uani 0.35(6) 1 d PDU D 1 H17A_2 H 0.7547 0.3833 0.9248 0.111 Uiso 0.35(6) 1 calc PR D 1 H17B_2 H 0.7944 0.2295 0.9046 0.111 Uiso 0.35(6) 1 calc PR D 1 H17C_2 H 0.6624 0.3388 0.8665 0.111 Uiso 0.35(6) 1 calc PR D 1 C16'_2 C 0.875(2) 0.3247(14) 0.7917(11) 0.086(4) Uani 0.65(6) 1 d PDU D 2 H16C_2 H 0.8345 0.4129 0.7662 0.103 Uiso 0.65(6) 1 calc PR D 2 H16D_2 H 0.9774 0.3046 0.7927 0.103 Uiso 0.65(6) 1 calc PR D 2 C17'_2 C 0.804(4) 0.335(2) 0.8855(10) 0.118(6) Uani 0.65(6) 1 d PDU D 2 H17D_2 H 0.8167 0.4050 0.9171 0.177 Uiso 0.65(6) 1 calc PR D 2 H17E_2 H 0.8478 0.2501 0.9135 0.177 Uiso 0.65(6) 1 calc PR D 2 H17F_2 H 0.7027 0.3549 0.8861 0.177 Uiso 0.65(6) 1 calc PR D 2 C18_2 C 0.7148(4) 0.2531(4) 0.7156(3) 0.0928(12) Uani 1 1 d DU D . H18A_2 H 0.6573 0.2523 0.7720 0.111 Uiso 1 1 calc R . . H18B_2 H 0.7146 0.1814 0.6779 0.111 Uiso 1 1 calc R . . C19_2 C 0.6423(4) 0.3866(4) 0.6729(3) 0.0916(12) Uani 1 1 d DU . . H19A_2 H 0.5450 0.3984 0.6659 0.137 Uiso 1 1 calc R D . H19B_2 H 0.6958 0.3874 0.6157 0.137 Uiso 1 1 calc R . . H19C_2 H 0.6402 0.4589 0.7100 0.137 Uiso 1 1 calc R . . C20_2 C 0.962(2) 0.2425(18) 0.6561(8) 0.071(3) Uani 0.51(3) 1 d PDU D 1 H20A_2 H 1.0563 0.2195 0.6759 0.085 Uiso 0.51(3) 1 calc PR D 1 H20B_2 H 0.9268 0.3379 0.6433 0.085 Uiso 0.51(3) 1 calc PR D 1 C21_2 C 0.9855(17) 0.1654(10) 0.5707(5) 0.069(3) Uani 0.51(3) 1 d PDU D 1 H21A_2 H 1.0599 0.1797 0.5302 0.103 Uiso 0.51(3) 1 calc PR D 1 H21B_2 H 0.8969 0.1963 0.5450 0.103 Uiso 0.51(3) 1 calc PR D 1 H21C_2 H 1.0146 0.0709 0.5821 0.103 Uiso 0.51(3) 1 calc PR D 1 C20'_2 C 0.945(2) 0.2198(19) 0.6436(10) 0.086(4) Uani 0.49(3) 1 d PDU D 2 H20C_2 H 1.0475 0.1918 0.6491 0.103 Uiso 0.49(3) 1 calc PR D 2 H20D_2 H 0.9126 0.3093 0.6193 0.103 Uiso 0.49(3) 1 calc PR D 2 C21'_2 C 0.925(2) 0.1252(19) 0.5837(11) 0.102(6) Uani 0.49(3) 1 d PDU D 2 H21D_2 H 0.9746 0.1277 0.5254 0.153 Uiso 0.49(3) 1 calc PR D 2 H21E_2 H 0.8238 0.1503 0.5809 0.153 Uiso 0.49(3) 1 calc PR D 2 H21F_2 H 0.9648 0.0354 0.6056 0.153 Uiso 0.49(3) 1 calc PR D 2 C22_2 C 0.9175(4) 0.0861(3) 0.7667(2) 0.0758(9) Uani 1 1 d U D . H22A_2 H 0.8508 0.0832 0.8183 0.091 Uiso 1 1 calc R . . H22B_2 H 0.9171 0.0228 0.7222 0.091 Uiso 1 1 calc R . . C23_2 C 1.0642(4) 0.0405(4) 0.7922(3) 0.0888(12) Uani 1 1 d U . . H23A_2 H 1.0904 -0.0487 0.8150 0.133 Uiso 1 1 calc R D . H23B_2 H 1.0658 0.1013 0.8372 0.133 Uiso 1 1 calc R . . H23C_2 H 1.1322 0.0394 0.7411 0.133 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 Cu 0.03653(17) 0.04012(18) 0.04285(18) -0.00317(12) -0.00871(12) -0.01359(12) C6 0.0495(14) 0.0545(16) 0.0514(15) -0.0046(12) -0.0069(12) -0.0152(12) F7 0.0614(11) 0.1047(16) 0.1043(16) -0.0502(13) -0.0225(10) -0.0200(11) F8 0.145(2) 0.1030(16) 0.0473(10) -0.0109(10) 0.0139(12) -0.0626(15) F9 0.0892(13) 0.0564(11) 0.0735(12) -0.0140(9) -0.0169(10) -0.0130(9) C1 0.0530(16) 0.0635(18) 0.0694(19) 0.0054(15) -0.0073(14) -0.0273(14) F1 0.088(5) 0.111(5) 0.097(4) 0.056(4) -0.032(4) -0.055(4) F2 0.072(4) 0.113(5) 0.102(4) 0.023(3) -0.026(3) -0.068(4) F3 0.095(6) 0.105(5) 0.163(9) -0.048(6) 0.071(6) -0.054(4) C1' 0.0530(16) 0.0635(18) 0.0694(19) 0.0054(15) -0.0073(14) -0.0273(14) F1' 0.094(8) 0.054(4) 0.156(12) -0.004(5) 0.020(6) -0.044(4) F2' 0.055(6) 0.200(15) 0.123(10) 0.073(9) -0.033(6) -0.073(8) F3' 0.118(12) 0.121(9) 0.074(5) -0.024(5) 0.036(5) -0.073(8) C5 0.063(2) 0.070(2) 0.110(3) 0.034(2) -0.033(2) -0.0314(18) F4 0.106(5) 0.115(5) 0.076(4) 0.051(3) -0.031(3) -0.035(4) F5 0.132(7) 0.157(12) 0.190(13) 0.116(8) -0.117(8) -0.096(8) F6 0.103(6) 0.044(4) 0.142(6) 0.001(4) -0.001(5) -0.004(3) C5' 0.063(2) 0.070(2) 0.110(3) 0.034(2) -0.033(2) -0.0314(18) F4' 0.148(11) 0.187(12) 0.099(5) 0.062(5) -0.037(6) 0.001(8) F5' 0.057(4) 0.079(5) 0.166(11) 0.055(6) -0.062(4) -0.026(3) F6' 0.072(5) 0.065(5) 0.229(12) 0.068(6) -0.076(6) -0.043(4) C10 0.069(2) 0.0458(17) 0.098(3) -0.0057(16) -0.0401(18) -0.0090(14) F10 0.117(7) 0.122(8) 0.106(4) -0.048(4) -0.029(3) 0.056(5) F11 0.108(6) 0.041(3) 0.272(12) 0.011(6) -0.105(7) -0.028(4) F12 0.052(3) 0.042(5) 0.159(8) 0.008(3) -0.044(4) -0.011(3) C10' 0.069(2) 0.0458(17) 0.098(3) -0.0057(16) -0.0401(18) -0.0090(14) F10' 0.075(5) 0.062(5) 0.099(5) -0.026(4) -0.023(4) -0.002(4) F11' 0.097(6) 0.038(5) 0.093(6) 0.020(3) -0.049(4) -0.030(4) F12' 0.055(5) 0.041(8) 0.101(8) 0.002(4) -0.035(4) -0.006(4) C11 0.071(2) 0.092(3) 0.086(3) -0.013(2) 0.0074(19) -0.033(2) F13 0.159(10) 0.203(10) 0.079(4) 0.010(4) 0.014(4) -0.135(9) F14 0.070(4) 0.107(5) 0.246(15) -0.036(6) 0.045(6) -0.013(4) F15 0.084(5) 0.108(5) 0.106(5) -0.016(4) -0.020(4) -0.056(4) C11' 0.071(2) 0.092(3) 0.086(3) -0.013(2) 0.0074(19) -0.033(2) F13' 0.108(9) 0.276(19) 0.094(5) -0.033(7) 0.028(5) -0.105(11) F14' 0.051(5) 0.123(7) 0.172(11) -0.025(6) -0.032(7) -0.014(4) F15' 0.115(10) 0.095(6) 0.172(13) -0.015(7) 0.036(8) -0.065(6) C15 0.182(4) 0.108(3) 0.052(2) 0.004(2) -0.019(2) -0.099(3) F16 0.231(8) 0.342(17) 0.114(7) -0.017(10) -0.055(6) -0.213(9) F17 0.246(10) 0.135(8) 0.039(3) 0.016(4) -0.036(4) -0.135(8) F18 0.366(15) 0.112(4) 0.067(3) -0.027(3) 0.026(6) -0.163(7) C15' 0.182(4) 0.108(3) 0.052(2) 0.004(2) -0.019(2) -0.099(3) F16' 0.148(7) 0.130(7) 0.107(7) 0.017(4) -0.084(6) -0.066(5) F17' 0.188(10) 0.123(10) 0.054(6) -0.033(6) 0.018(6) -0.086(7) F18' 0.206(13) 0.118(7) 0.070(4) 0.020(5) -0.042(7) -0.125(8) O1 0.0419(9) 0.0506(10) 0.0539(10) 0.0030(8) -0.0116(8) -0.0149(8) O2 0.0408(9) 0.0446(10) 0.0683(12) 0.0046(8) -0.0115(8) -0.0206(8) O3 0.0360(8) 0.0546(10) 0.0487(10) -0.0047(8) -0.0071(7) -0.0100(8) O4 0.0514(10) 0.0484(10) 0.0608(11) -0.0061(8) -0.0201(9) -0.0148(8) O5 0.0548(11) 0.0634(12) 0.0519(11) -0.0137(9) -0.0050(9) -0.0177(9) O6 0.0594(11) 0.0543(11) 0.0545(11) -0.0003(9) -0.0147(9) -0.0230(9) C2 0.0400(13) 0.0465(14) 0.0516(14) -0.0065(11) -0.0063(10) -0.0184(11) C3 0.0381(13) 0.0513(15) 0.0724(18) 0.0070(13) -0.0189(12) -0.0189(11) C4 0.0474(14) 0.0435(14) 0.0632(16) 0.0028(12) -0.0167(12) -0.0191(11) C7 0.0365(12) 0.0504(14) 0.0411(12) 0.0017(10) -0.0042(10) -0.0200(10) C8 0.0444(13) 0.0482(14) 0.0508(14) 0.0022(11) -0.0169(11) -0.0164(11) C9 0.0432(13) 0.0444(13) 0.0540(15) 0.0045(11) -0.0121(11) -0.0174(11) C12 0.0562(15) 0.0478(15) 0.0516(16) -0.0014(12) -0.0055(12) -0.0135(12) C13 0.088(2) 0.0615(18) 0.0418(15) -0.0047(13) 0.0029(14) -0.0332(16) C14 0.086(2) 0.0469(15) 0.0403(14) 0.0052(11) -0.0182(14) -0.0269(14) N_2 0.0497(12) 0.0427(12) 0.0561(13) 0.0040(10) -0.0095(10) -0.0243(10) C16_2 0.046(7) 0.040(6) 0.048(7) 0.003(5) -0.003(4) -0.017(5) C17_2 0.090(12) 0.074(8) 0.044(7) 0.005(6) 0.008(6) -0.020(8) C16'_2 0.097(9) 0.069(5) 0.102(7) -0.023(5) -0.019(6) -0.040(5) C17'_2 0.128(14) 0.109(9) 0.081(6) -0.029(6) -0.018(6) -0.003(7) C18_2 0.071(2) 0.084(3) 0.139(4) 0.000(2) -0.036(2) -0.039(2) C19_2 0.068(2) 0.085(3) 0.100(3) 0.002(2) -0.025(2) -0.0019(19) C20_2 0.087(6) 0.080(6) 0.044(4) -0.011(4) 0.011(4) -0.034(5) C21_2 0.091(7) 0.062(5) 0.040(3) -0.006(3) -0.009(3) -0.014(4) C20'_2 0.081(6) 0.087(9) 0.060(6) 0.021(5) -0.011(5) 0.001(6) C21'_2 0.099(9) 0.091(9) 0.094(7) -0.012(6) -0.027(7) -0.007(7) C22_2 0.101(3) 0.0509(17) 0.081(2) 0.0107(16) -0.021(2) -0.0329(18) C23_2 0.101(3) 0.067(2) 0.083(2) -0.0061(18) -0.045(2) -0.004(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu O1 2.2056(18) . ? Cu O2 1.9739(18) . ? Cu O3 2.0089(18) . ? Cu O4 1.9769(18) . ? Cu O5 2.216(2) . ? Cu O6 1.9965(19) . ? C6 F7 1.310(3) . ? C6 F8 1.319(3) . ? C6 F9 1.316(3) . ? C6 C7 1.529(4) . ? C1 F1 1.314(7) . ? C1 F2 1.328(7) . ? C1 F3 1.282(9) . ? C1 C2 1.536(4) . ? C5 F4 1.321(9) . ? C5 F5 1.285(10) . ? C5 F6 1.333(8) . ? C5 C4 1.525(4) . ? C10 F10 1.359(10) . ? C10 F11 1.271(9) . ? C10 F12 1.315(8) . ? C10 C9 1.527(4) . ? C11 F13 1.345(9) . ? C11 F14 1.270(10) . ? C11 F15 1.311(8) . ? C11 C12 1.535(5) . ? C15 F16 1.240(10) . ? C15 F17 1.299(9) . ? C15 F18 1.396(10) . ? C15 C14 1.521(5) . ? O1 C2 1.234(3) . ? O2 C4 1.250(3) . ? O3 C7 1.241(3) . ? O4 C9 1.251(3) . ? O5 C12 1.226(3) . ? O6 C14 1.252(4) . ? C2 C3 1.386(4) . ? C3 H3 0.950 . ? C3 C4 1.369(4) . ? C7 C8 1.384(4) . ? C8 H8 0.950 . ? C8 C9 1.373(4) . ? C12 C13 1.390(4) . ? C13 H13 0.950 . ? C13 C14 1.369(5) . ? N_2 C16_2 1.522(13) . ? N_2 C16'_2 1.520(9) . ? N_2 C18_2 1.485(4) . ? N_2 C20_2 1.506(13) . ? N_2 C20'_2 1.491(15) . ? N_2 C22_2 1.510(4) . ? C16_2 H16A_2 0.990 . ? C16_2 H16B_2 0.990 . ? C16_2 C17_2 1.525(13) . ? C17_2 H17A_2 0.980 . ? C17_2 H17B_2 0.980 . ? C17_2 H17C_2 0.980 . ? C16'_2 H16C_2 0.990 . ? C16'_2 H16D_2 0.990 . ? C16'_2 C17'_2 1.522(11) . ? C17'_2 H17D_2 0.980 . ? C17'_2 H17E_2 0.980 . ? C17'_2 H17F_2 0.980 . ? C18_2 H18A_2 0.990 . ? C18_2 H18B_2 0.990 . ? C18_2 C19_2 1.544(5) . ? C19_2 H19A_2 0.980 . ? C19_2 H19B_2 0.980 . ? C19_2 H19C_2 0.980 . ? C20_2 H20A_2 0.990 . ? C20_2 H20B_2 0.990 . ? C20_2 C21_2 1.527(10) . ? C21_2 H21A_2 0.980 . ? C21_2 H21B_2 0.980 . ? C21_2 H21C_2 0.980 . ? C20'_2 H20C_2 0.990 . ? C20'_2 H20D_2 0.990 . ? C20'_2 C21'_2 1.495(12) . ? C21'_2 H21D_2 0.980 . ? C21'_2 H21E_2 0.980 . ? C21'_2 H21F_2 0.980 . ? C22_2 H22A_2 0.990 . ? C22_2 H22B_2 0.990 . ? C22_2 C23_2 1.503(5) . ? C23_2 H23A_2 0.980 . ? C23_2 H23B_2 0.980 . ? C23_2 H23C_2 0.980 . ? 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 Cu O2 88.24(7) . . ? O1 Cu O3 90.88(7) . . ? O1 Cu O4 93.57(8) . . ? O1 Cu O5 178.94(7) . . ? O1 Cu O6 91.97(8) . . ? O2 Cu O3 92.29(8) . . ? O2 Cu O4 176.08(8) . . ? O2 Cu O5 91.02(7) . . ? O2 Cu O6 88.39(8) . . ? O3 Cu O4 91.16(7) . . ? O3 Cu O5 88.38(7) . . ? O3 Cu O6 177.09(7) . . ? O4 Cu O5 87.20(8) . . ? O4 Cu O6 88.07(8) . . ? O5 Cu O6 88.78(8) . . ? F7 C6 F8 106.9(3) . . ? F7 C6 F9 107.9(2) . . ? F7 C6 C7 112.8(2) . . ? F8 C6 F9 105.3(2) . . ? F8 C6 C7 110.4(2) . . ? F9 C6 C7 113.1(2) . . ? F1 C1 F2 104.2(6) . . ? F1 C1 F3 109.0(9) . . ? F1 C1 C2 113.7(6) . . ? F2 C1 F3 107.4(7) . . ? F2 C1 C2 109.7(5) . . ? F3 C1 C2 112.4(8) . . ? F4 C5 F5 105.7(10) . . ? F4 C5 F6 104.0(7) . . ? F4 C5 C4 108.7(6) . . ? F5 C5 F6 111.9(10) . . ? F5 C5 C4 115.5(8) . . ? F6 C5 C4 110.3(7) . . ? F10 C10 F11 109.3(6) . . ? F10 C10 F12 98.7(11) . . ? F10 C10 C9 108.9(5) . . ? F11 C10 F12 111.3(11) . . ? F11 C10 C9 116.6(8) . . ? F12 C10 C9 110.5(9) . . ? F13 C11 F14 109.2(9) . . ? F13 C11 F15 104.5(8) . . ? F13 C11 C12 108.9(7) . . ? F14 C11 F15 108.7(10) . . ? F14 C11 C12 113.8(9) . . ? F15 C11 C12 111.3(7) . . ? F16 C15 F17 113.9(9) . . ? F16 C15 F18 107.0(7) . . ? F16 C15 C14 114.2(7) . . ? F17 C15 F18 102.7(9) . . ? F17 C15 C14 114.1(7) . . ? F18 C15 C14 103.4(6) . . ? Cu O1 C2 120.23(17) . . ? Cu O2 C4 124.61(17) . . ? Cu O3 C7 123.27(16) . . ? Cu O4 C9 122.56(17) . . ? Cu O5 C12 121.27(19) . . ? Cu O6 C14 125.96(19) . . ? C1 C2 O1 115.4(2) . . ? C1 C2 C3 115.6(2) . . ? O1 C2 C3 129.0(2) . . ? C2 C3 H3 118.2 . . ? C2 C3 C4 123.6(2) . . ? H3 C3 C4 118.2 . . ? C5 C4 O2 112.6(2) . . ? C5 C4 C3 117.7(2) . . ? O2 C4 C3 129.6(3) . . ? C6 C7 O3 115.1(2) . . ? C6 C7 C8 116.5(2) . . ? O3 C7 C8 128.4(2) . . ? C7 C8 H8 118.9 . . ? C7 C8 C9 122.2(2) . . ? H8 C8 C9 118.9 . . ? C10 C9 O4 112.7(2) . . ? C10 C9 C8 118.2(2) . . ? O4 C9 C8 129.1(2) . . ? C11 C12 O5 114.7(3) . . ? C11 C12 C13 116.5(3) . . ? O5 C12 C13 128.8(3) . . ? C12 C13 H13 117.7 . . ? C12 C13 C14 124.6(3) . . ? H13 C13 C14 117.7 . . ? C15 C14 O6 112.2(3) . . ? C15 C14 C13 117.7(3) . . ? O6 C14 C13 130.1(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 Cu O1 C2 -15.72(19) . . . . ? O3 Cu O1 C2 -107.98(19) . . . . ? O4 Cu O1 C2 160.80(19) . . . . ? O5 Cu O1 C2 -62(4) . . . . ? O6 Cu O1 C2 72.61(19) . . . . ? O1 Cu O2 C4 22.9(2) . . . . ? O3 Cu O2 C4 113.7(2) . . . . ? O4 Cu O2 C4 -94.8(11) . . . . ? O5 Cu O2 C4 -157.9(2) . . . . ? O6 Cu O2 C4 -69.1(2) . . . . ? O1 Cu O3 C7 -106.94(19) . . . . ? O2 Cu O3 C7 164.78(19) . . . . ? O4 Cu O3 C7 -13.3(2) . . . . ? O5 Cu O3 C7 73.8(2) . . . . ? O6 Cu O3 C7 61.3(15) . . . . ? O1 Cu O4 C9 110.3(2) . . . . ? O2 Cu O4 C9 -132.2(10) . . . . ? O3 Cu O4 C9 19.3(2) . . . . ? O5 Cu O4 C9 -69.0(2) . . . . ? O6 Cu O4 C9 -157.9(2) . . . . ? O1 Cu O5 C12 141(4) . . . . ? O2 Cu O5 C12 95.0(2) . . . . ? O3 Cu O5 C12 -172.8(2) . . . . ? O4 Cu O5 C12 -81.5(2) . . . . ? O6 Cu O5 C12 6.6(2) . . . . ? O1 Cu O6 C14 178.8(2) . . . . ? O2 Cu O6 C14 -93.0(2) . . . . ? O3 Cu O6 C14 10.6(16) . . . . ? O4 Cu O6 C14 85.3(2) . . . . ? O5 Cu O6 C14 -2.0(2) . . . . ? Cu O1 C2 C1 -177.85(17) . . . . ? Cu O1 C2 C3 3.9(4) . . . . ? F1 C1 C2 O1 13.8(7) . . . . ? F1 C1 C2 C3 -167.8(7) . . . . ? F2 C1 C2 O1 130.0(6) . . . . ? F2 C1 C2 C3 -51.6(7) . . . . ? F3 C1 C2 O1 -110.6(11) . . . . ? F3 C1 C2 C3 67.8(11) . . . . ? C1 C2 C3 C4 -169.6(3) . . . . ? O1 C2 C3 C4 8.6(5) . . . . ? Cu O2 C4 C5 162.0(2) . . . . ? Cu O2 C4 C3 -19.9(4) . . . . ? C2 C3 C4 C5 177.4(3) . . . . ? C2 C3 C4 O2 -0.6(5) . . . . ? F4 C5 C4 O2 -44.3(7) . . . . ? F4 C5 C4 C3 137.3(7) . . . . ? F5 C5 C4 O2 -162.8(15) . . . . ? F5 C5 C4 C3 18.8(15) . . . . ? F6 C5 C4 O2 69.1(7) . . . . ? F6 C5 C4 C3 -109.2(7) . . . . ? Cu O3 C7 C6 -179.12(16) . . . . ? Cu O3 C7 C8 3.0(4) . . . . ? F7 C6 C7 O3 142.9(3) . . . . ? F7 C6 C7 C8 -39.0(3) . . . . ? F8 C6 C7 O3 -97.6(3) . . . . ? F8 C6 C7 C8 80.5(3) . . . . ? F9 C6 C7 O3 20.1(3) . . . . ? F9 C6 C7 C8 -161.7(2) . . . . ? C6 C7 C8 C9 -170.3(2) . . . . ? O3 C7 C8 C9 7.6(4) . . . . ? Cu O4 C9 C10 165.5(2) . . . . ? Cu O4 C9 C8 -16.4(4) . . . . ? C7 C8 C9 C10 178.1(3) . . . . ? C7 C8 C9 O4 0.1(5) . . . . ? F10 C10 C9 O4 -53.6(12) . . . . ? F10 C10 C9 C8 128.1(12) . . . . ? F11 C10 C9 O4 70.6(10) . . . . ? F11 C10 C9 C8 -107.7(10) . . . . ? F12 C10 C9 O4 -161.0(9) . . . . ? F12 C10 C9 C8 20.7(9) . . . . ? Cu O5 C12 C11 171.1(2) . . . . ? Cu O5 C12 C13 -8.3(4) . . . . ? F13 C11 C12 O5 133.3(10) . . . . ? F13 C11 C12 C13 -47.2(10) . . . . ? F14 C11 C12 O5 -104.7(13) . . . . ? F14 C11 C12 C13 74.9(13) . . . . ? F15 C11 C12 O5 18.6(8) . . . . ? F15 C11 C12 C13 -161.9(8) . . . . ? C11 C12 C13 C14 -175.8(3) . . . . ? O5 C12 C13 C14 3.7(5) . . . . ? Cu O6 C14 C15 178.7(2) . . . . ? Cu O6 C14 C13 -1.8(5) . . . . ? C12 C13 C14 C15 -177.9(3) . . . . ? C12 C13 C14 O6 2.6(6) . . . . ? F16 C15 C14 O6 -35.7(12) . . . . ? F16 C15 C14 C13 144.7(12) . . . . ? F17 C15 C14 O6 -169.1(9) . . . . ? F17 C15 C14 C13 11.3(10) . . . . ? F18 C15 C14 O6 80.2(8) . . . . ? F18 C15 C14 C13 -99.4(8) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.43 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.513 _refine_diff_density_min -0.275 _refine_diff_density_rms 0.048 _geom_extra_table_head_A 'Bond angles for disordered counterion' loop_ _geom_extra_tableA_col_1 _geom_extra_tableA_col_2 _geom_extra_tableA_col_3 _geom_extra_tableA_col_4 _geom_extra_tableA_col_5 _geom_extra_tableA_col_6 _geom_extra_tableA_col_7 C18_2 N_2 C20'_2 105.9(8) . . ? C18_2 N_2 C20_2 116.8(8) . . ? C20'_2 N_2 C20_2 16.0(9) . . ? C18_2 N_2 C22_2 106.7(2) . . ? C20'_2 N_2 C22_2 108.2(8) . . ? C20_2 N_2 C22_2 113.2(8) . . ? C18_2 N_2 C16'_2 113.0(9) . . ? C20'_2 N_2 C16'_2 110.9(12) . . ? C20_2 N_2 C16'_2 95.3(10) . . ? C22_2 N_2 C16'_2 111.8(7) . . ? C18_2 N_2 C16_2 106.8(9) . . ? C20'_2 N_2 C16_2 118.6(12) . . ? C20_2 N_2 C16_2 103.1(9) . . ? C22_2 N_2 C16_2 110.0(8) . . ? C16'_2 N_2 C16_2 8.2(14) . . ? N_2 C16_2 C17_2 110.1(17) . . ? N_2 C16_2 H16A_2 109.6 . . ? C17_2 C16_2 H16A_2 109.6 . . ? N_2 C16_2 H16B_2 109.6 . . ? C17_2 C16_2 H16B_2 109.6 . . ? H16A_2 C16_2 H16B_2 108.2 . . ? C16_2 C17_2 H17A_2 109.5 . . ? C16_2 C17_2 H17B_2 109.5 . . ? H17A_2 C17_2 H17B_2 109.5 . . ? C16_2 C17_2 H17C_2 109.5 . . ? H17A_2 C17_2 H17C_2 109.5 . . ? H17B_2 C17_2 H17C_2 109.5 . . ? N_2 C16'_2 C17'_2 117.3(12) . . ? N_2 C16'_2 H16C_2 108.0 . . ? C17'_2 C16'_2 H16C_2 108.0 . . ? N_2 C16'_2 H16D_2 108.0 . . ? C17'_2 C16'_2 H16D_2 108.0 . . ? H16C_2 C16'_2 H16D_2 107.2 . . ? C16'_2 C17'_2 H17D_2 109.5 . . ? C16'_2 C17'_2 H17E_2 109.5 . . ? H17D_2 C17'_2 H17E_2 109.5 . . ? C16'_2 C17'_2 H17F_2 109.5 . . ? H17D_2 C17'_2 H17F_2 109.5 . . ? H17E_2 C17'_2 H17F_2 109.5 . . ? N_2 C18_2 C19_2 115.1(3) . . ? N_2 C18_2 H18A_2 108.5 . . ? C19_2 C18_2 H18A_2 108.5 . . ? N_2 C18_2 H18B_2 108.5 . . ? C19_2 C18_2 H18B_2 108.5 . . ? H18A_2 C18_2 H18B_2 107.5 . . ? C18_2 C19_2 H19A_2 109.5 . . ? C18_2 C19_2 H19B_2 109.5 . . ? H19A_2 C19_2 H19B_2 109.5 . . ? C18_2 C19_2 H19C_2 109.5 . . ? H19A_2 C19_2 H19C_2 109.5 . . ? H19B_2 C19_2 H19C_2 109.5 . . ? N_2 C20_2 C21_2 118.4(9) . . ? N_2 C20_2 H20A_2 107.7 . . ? C21_2 C20_2 H20A_2 107.7 . . ? N_2 C20_2 H20B_2 107.7 . . ? C21_2 C20_2 H20B_2 107.7 . . ? H20A_2 C20_2 H20B_2 107.1 . . ? C20_2 C21_2 H21A_2 109.5 . . ? C20_2 C21_2 H21B_2 109.5 . . ? H21A_2 C21_2 H21B_2 109.5 . . ? C20_2 C21_2 H21C_2 109.5 . . ? H21A_2 C21_2 H21C_2 109.5 . . ? H21B_2 C21_2 H21C_2 109.5 . . ? N_2 C20'_2 C21'_2 110.0(12) . . ? N_2 C20'_2 H20C_2 109.7 . . ? C21'_2 C20'_2 H20C_2 109.7 . . ? N_2 C20'_2 H20D_2 109.7 . . ? C21'_2 C20'_2 H20D_2 109.7 . . ? H20C_2 C20'_2 H20D_2 108.2 . . ? C20'_2 C21'_2 H21D_2 109.5 . . ? C20'_2 C21'_2 H21E_2 109.5 . . ? H21D_2 C21'_2 H21E_2 109.5 . . ? C20'_2 C21'_2 H21F_2 109.5 . . ? H21D_2 C21'_2 H21F_2 109.5 . . ? H21E_2 C21'_2 H21F_2 109.5 . . ? C23_2 C22_2 N_2 115.0(3) . . ? C23_2 C22_2 H22A_2 108.5 . . ? N_2 C22_2 H22A_2 108.5 . . ? C23_2 C22_2 H22B_2 108.5 . . ? N_2 C22_2 H22B_2 108.5 . . ? H22A_2 C22_2 H22B_2 107.5 . . ? C22_2 C23_2 H23A_2 109.5 . . ? C22_2 C23_2 H23B_2 109.5 . . ? H23A_2 C23_2 H23B_2 109.5 . . ? C22_2 C23_2 H23C_2 109.5 . . ? H23A_2 C23_2 H23C_2 109.5 . . ? H23B_2 C23_2 H23C_2 109.5 . . ? _geom_extra_table_head_B 'Torsion angles for disordered counterion' loop_ _geom_extra_tableB_col_1 _geom_extra_tableB_col_2 _geom_extra_tableB_col_3 _geom_extra_tableB_col_4 _geom_extra_tableB_col_5 _geom_extra_tableB_col_6 _geom_extra_tableB_col_7 _geom_extra_tableB_col_8 _geom_extra_tableB_col_9 _geom_extra_tableB_col_10 C18_2 N_2 C16_2 C17_2 56.3(18) . . . . ? C20'_2 N_2 C16_2 C17_2 175.7(16) . . . . ? C20_2 N_2 C16_2 C17_2 179.9(17) . . . . ? C22_2 N_2 C16_2 C17_2 -59.1(18) . . . . ? C16'_2 N_2 C16_2 C17_2 -163(11) . . . . ? C18_2 N_2 C16'_2 C17'_2 64.9(16) . . . . ? C20'_2 N_2 C16'_2 C17'_2 -176.4(14) . . . . ? C20_2 N_2 C16'_2 C17'_2 -173.1(16) . . . . ? C22_2 N_2 C16'_2 C17'_2 -55.5(15) . . . . ? C16_2 N_2 C16'_2 C17'_2 23(9) . . . . ? C20'_2 N_2 C18_2 C19_2 -60.9(9) . . . . ? C20_2 N_2 C18_2 C19_2 -48.3(8) . . . . ? C22_2 N_2 C18_2 C19_2 -176.0(3) . . . . ? C16'_2 N_2 C18_2 C19_2 60.7(9) . . . . ? C16_2 N_2 C18_2 C19_2 66.4(9) . . . . ? C18_2 N_2 C20_2 C21_2 -57.8(17) . . . . ? C20'_2 N_2 C20_2 C21_2 -8(4) . . . . ? C22_2 N_2 C20_2 C21_2 66.7(16) . . . . ? C16'_2 N_2 C20_2 C21_2 -176.9(15) . . . . ? C16_2 N_2 C20_2 C21_2 -174.6(15) . . . . ? C18_2 N_2 C20'_2 C21'_2 -53.9(12) . . . . ? C20_2 N_2 C20'_2 C21'_2 171(6) . . . . ? C22_2 N_2 C20'_2 C21'_2 60.2(13) . . . . ? C16'_2 N_2 C20'_2 C21'_2 -176.9(12) . . . . ? C16_2 N_2 C20'_2 C21'_2 -173.7(13) . . . . ? C18_2 N_2 C22_2 C23_2 -176.3(3) . . . . ? C20'_2 N_2 C22_2 C23_2 70.2(10) . . . . ? C20_2 N_2 C22_2 C23_2 53.9(7) . . . . ? C16'_2 N_2 C22_2 C23_2 -52.2(10) . . . . ? C16_2 N_2 C22_2 C23_2 -60.8(10) . . . . ? data_jtn102 _database_code_depnum_ccdc_archive 'CCDC 886192' #TrackingRef 'web_deposit_cif_file_1_JonT.Njardarson_1339529666.2_Nihfacac3NEt4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H20 N +, C15 H3 F18 Ni O6 -, 0.5 C6 H14' _chemical_formula_sum 'C26 H30 F18 N Ni O6' _chemical_formula_weight 853.22 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 '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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.9155(6) _cell_length_b 10.9991(6) _cell_length_c 15.6366(9) _cell_angle_alpha 83.547(3) _cell_angle_beta 90.332(3) _cell_angle_gamma 70.468(3) _cell_volume 1595.32(16) _cell_formula_units_Z 2 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used 9952 _cell_measurement_theta_min 2.18 _cell_measurement_theta_max 26.84 _exptl_crystal_description blade _exptl_crystal_colour colourless _exptl_crystal_size_max 0.89 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.776 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 862 _exptl_absorpt_coefficient_mu 0.756 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.5520 _exptl_absorpt_correction_T_max 0.9561 _exptl_absorpt_process_details 'SADABS; Sheldrick, 1996' _exptl_special_details ; The crystal used cracked at low temperature (below ~200K), which results in multiple, overlapped diffraction patterns. However a single component of data at 100K was obtained and refinement is quite satisfactory. A re-determination at 220K, using a different crystal, yields similar refinement residuals, but suffers from greater CF3 disorder and poorer (0.87 vs 0.75 ) data resolution. The data were treated with the SQUEEZE routine of PLATON to remove one molecule of solvent hexane per asymmetric unit, which was disordered over an inversion centre and could not be modeled satisfactorily. ; _diffrn_ambient_temperature 103(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube with Miracol optics' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Kappa APEXII DUO CCD diffractometer' _diffrn_measurement_method 'thin-slice \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 81970 _diffrn_reflns_av_R_equivalents 0.0425 _diffrn_reflns_av_sigmaI/netI 0.0223 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 28.28 _reflns_number_total 7908 _reflns_number_gt 6539 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 (Bruker, 2007)' _computing_cell_refinement 'SAINT (Bruker, 2007)' _computing_data_reduction SAINT _computing_structure_solution 'SIR2004 (Burla et al., 2005)' _computing_structure_refinement SHELXTL _computing_molecular_graphics 'ORTEP3 for Windows (Farrugia, 1997)' _computing_publication_material 'SHELXTL and local programs' _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^)+(0.0247P)^2^+2.8243P] 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 7908 _refine_ls_number_parameters 502 _refine_ls_number_restraints 95 _refine_ls_R_factor_all 0.0555 _refine_ls_R_factor_gt 0.0442 _refine_ls_wR_factor_ref 0.1028 _refine_ls_wR_factor_gt 0.0977 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.131 _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 Ni Ni 0.92953(3) 0.15884(3) 0.72160(2) 0.02194(8) Uani 1 1 d . . . C1 C 0.7589(2) 0.0878(2) 0.48522(16) 0.0223(5) Uani 1 1 d D . . F1 F 0.8222(2) 0.12992(17) 0.41896(10) 0.0401(4) Uani 1 1 d D . . F2 F 0.62382(18) 0.11179(19) 0.45922(14) 0.0503(5) Uani 1 1 d D . . F3 F 0.8218(2) -0.03994(14) 0.49828(11) 0.0401(4) Uani 1 1 d D . . F4 F 0.6008(2) 0.57963(16) 0.59508(19) 0.0693(8) Uani 1 1 d . . . F5 F 0.5266(2) 0.5083(2) 0.71206(18) 0.0805(9) Uani 1 1 d . . . F6 F 0.43878(16) 0.49119(16) 0.58977(14) 0.0462(5) Uani 1 1 d . . . F7 F 1.2338(2) 0.34293(18) 0.58115(12) 0.0490(5) Uani 1 1 d . . . F8 F 1.3909(3) 0.1553(2) 0.57283(14) 0.0613(7) Uani 1 1 d . . . F9 F 1.39575(19) 0.25349(17) 0.68148(11) 0.0395(4) Uani 1 1 d . . . F10 F 1.23961(17) -0.21333(15) 0.86853(10) 0.0337(4) Uani 1 1 d . . . F11 F 1.33857(19) -0.25421(15) 0.75001(10) 0.0384(4) Uani 1 1 d . . . F12 F 1.42750(19) -0.16522(18) 0.83966(13) 0.0469(5) Uani 1 1 d . . . C11 C 0.6342(4) 0.0686(4) 0.8962(2) 0.0519(9) Uani 0.70(5) 1 d PDU A 1 F13 F 0.6426(18) 0.035(2) 0.9813(4) 0.069(3) Uani 0.70(5) 1 d PDU A 1 F14 F 0.5135(9) 0.1667(13) 0.8744(9) 0.085(2) Uani 0.70(5) 1 d PDU A 1 F15 F 0.625(2) -0.0325(15) 0.8609(11) 0.068(3) Uani 0.70(5) 1 d PD A 1 C11' C 0.6342(4) 0.0686(4) 0.8962(2) 0.0519(9) Uani 0.30(5) 1 d PDU A 2 F13' F 0.607(3) 0.085(3) 0.9775(11) 0.058(4) Uani 0.30(5) 1 d PDU A 2 F14' F 0.5081(18) 0.141(2) 0.8565(18) 0.062(4) Uani 0.30(5) 1 d PDU A 2 F15' F 0.657(2) -0.0550(13) 0.8819(17) 0.042(4) Uani 0.30(5) 1 d PD A 2 C15 C 1.0051(4) 0.2558(5) 0.97172(19) 0.0585(11) Uani 0.561(11) 1 d PDU A 1 F16 F 1.0280(15) 0.1723(12) 1.0435(5) 0.0354(19) Uani 0.561(11) 1 d PD A 1 F17 F 1.1524(6) 0.2280(9) 0.9503(2) 0.072(3) Uani 0.561(11) 1 d PD A 1 F18 F 0.9466(11) 0.3648(6) 0.9812(5) 0.090(3) Uani 0.561(11) 1 d PDU A 1 C15' C 1.0051(4) 0.2558(5) 0.97172(19) 0.0585(11) Uani 0.439(11) 1 d PD A 2 F16' F 1.0545(19) 0.1785(15) 1.0401(9) 0.048(4) Uani 0.439(11) 1 d PD A 2 F17' F 1.0818(7) 0.3335(7) 0.9477(3) 0.0430(19) Uani 0.439(11) 1 d PD A 2 F18' F 0.8856(7) 0.3615(6) 1.0084(4) 0.0398(14) Uani 0.439(11) 1 d PD A 2 O1 O 0.87988(19) 0.09328(16) 0.61346(11) 0.0255(4) Uani 1 1 d . . . O2 O 0.77537(19) 0.33407(16) 0.68867(11) 0.0252(4) Uani 1 1 d . . . O3 O 1.0780(2) 0.22110(16) 0.65857(11) 0.0277(4) Uani 1 1 d . . . O4 O 1.07895(18) -0.01700(16) 0.76113(11) 0.0218(3) Uani 1 1 d . . . O5 O 0.78057(18) 0.10058(16) 0.78679(11) 0.0235(3) Uani 1 1 d . A . O6 O 0.98400(18) 0.22526(16) 0.82786(11) 0.0236(4) Uani 1 1 d . A . C2 C 0.7735(2) 0.1535(2) 0.56489(15) 0.0190(4) Uani 1 1 d . . . C3 C 0.6692(3) 0.2739(2) 0.57093(18) 0.0271(5) Uani 1 1 d . . . H3 H 0.5884 0.3032 0.5315 0.033 Uiso 1 1 calc R . . C4 C 0.6794(2) 0.3522(2) 0.63261(16) 0.0218(5) Uani 1 1 d . . . C5 C 0.5592(3) 0.4831(3) 0.6320(2) 0.0428(8) Uani 1 1 d . . . C6 C 1.3053(2) -0.1672(2) 0.80587(15) 0.0209(5) Uani 1 1 d . . . C7 C 1.2103(3) -0.0342(2) 0.76120(14) 0.0200(4) Uani 1 1 d . . . C8 C 1.2804(3) 0.0471(2) 0.72340(16) 0.0239(5) Uani 1 1 d . . . H8 H 1.3813 0.0218 0.7326 0.029 Uiso 1 1 calc R . . C9 C 1.2089(3) 0.1639(2) 0.67266(16) 0.0248(5) Uani 1 1 d . . . C10 C 1.3070(3) 0.2302(3) 0.62628(17) 0.0323(6) Uani 1 1 d . . . C12 C 0.7602(3) 0.1100(3) 0.86400(17) 0.0302(6) Uani 1 1 d . . . C13 C 0.8338(4) 0.1538(5) 0.92238(19) 0.0576(11) Uani 1 1 d . A . H13 H 0.8113 0.1466 0.9813 0.069 Uiso 1 1 calc R . . C14 C 0.9380(3) 0.2075(3) 0.89939(16) 0.0320(6) Uani 1 1 d . . . N N 0.9186(2) 0.6583(2) 0.71568(16) 0.0305(5) Uani 1 1 d . . . C16 C 0.8348(3) 0.5873(3) 0.7690(2) 0.0400(7) Uani 1 1 d . . . H16A H 0.7432 0.6013 0.7372 0.048 Uiso 1 1 calc R . . H16B H 0.8895 0.4930 0.7749 0.048 Uiso 1 1 calc R . . C17 C 0.8020(4) 0.6270(3) 0.8577(2) 0.0490(8) Uani 1 1 d . . . H17A H 0.7459 0.5775 0.8866 0.073 Uiso 1 1 calc R . . H17B H 0.7469 0.7201 0.8530 0.073 Uiso 1 1 calc R . . H17C H 0.8917 0.6092 0.8912 0.073 Uiso 1 1 calc R . . C18 C 0.9389(3) 0.6031(3) 0.6300(2) 0.0367(7) Uani 1 1 d . . . H18A H 0.9810 0.5072 0.6417 0.044 Uiso 1 1 calc R . . H18B H 0.8433 0.6238 0.6012 0.044 Uiso 1 1 calc R . . C19 C 1.0319(3) 0.6506(3) 0.5682(2) 0.0411(7) Uani 1 1 d . . . H19A H 1.0340 0.6127 0.5142 0.062 Uiso 1 1 calc R . . H19B H 1.1294 0.6244 0.5938 0.062 Uiso 1 1 calc R . . H19C H 0.9927 0.7456 0.5565 0.062 Uiso 1 1 calc R . . C20 C 1.0613(3) 0.6398(3) 0.7601(2) 0.0411(7) Uani 1 1 d . . . H20A H 1.0433 0.6754 0.8160 0.049 Uiso 1 1 calc R . . H20B H 1.1102 0.6911 0.7245 0.049 Uiso 1 1 calc R . . C21 C 1.1615(4) 0.5000(4) 0.7766(3) 0.0622(11) Uani 1 1 d . . . H21A H 1.2522 0.4975 0.8033 0.093 Uiso 1 1 calc R . . H21B H 1.1796 0.4631 0.7219 0.093 Uiso 1 1 calc R . . H21C H 1.1173 0.4492 0.8153 0.093 Uiso 1 1 calc R . . C22 C 0.8402(3) 0.8045(2) 0.7033(2) 0.0333(6) Uani 1 1 d . . . H22A H 0.8381 0.8374 0.7598 0.040 Uiso 1 1 calc R . . H22B H 0.8959 0.8459 0.6651 0.040 Uiso 1 1 calc R . . C23 C 0.6887(3) 0.8472(3) 0.6657(2) 0.0437(8) Uani 1 1 d . . . H23A H 0.6474 0.9422 0.6601 0.065 Uiso 1 1 calc R . . H23B H 0.6312 0.8094 0.7038 0.065 Uiso 1 1 calc R . . H23C H 0.6892 0.8177 0.6088 0.065 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 Ni 0.02764(16) 0.01527(15) 0.01944(15) -0.00347(11) 0.00419(11) -0.00218(12) C1 0.0202(11) 0.0176(11) 0.0287(12) -0.0051(9) 0.0021(9) -0.0053(9) F1 0.0635(12) 0.0442(10) 0.0238(8) -0.0073(7) 0.0071(8) -0.0317(9) F2 0.0245(8) 0.0557(12) 0.0760(14) -0.0448(11) 0.0002(8) -0.0089(8) F3 0.0642(12) 0.0162(7) 0.0344(9) -0.0093(6) -0.0004(8) -0.0044(7) F4 0.0366(10) 0.0129(8) 0.155(2) -0.0039(10) -0.0389(12) -0.0064(7) F5 0.0410(11) 0.0814(17) 0.111(2) -0.0767(16) 0.0041(12) 0.0112(11) F6 0.0169(7) 0.0259(8) 0.0954(15) -0.0260(9) -0.0079(8) -0.0010(6) F7 0.0595(12) 0.0419(10) 0.0497(11) 0.0209(8) -0.0099(9) -0.0312(9) F8 0.0942(17) 0.0554(12) 0.0621(13) -0.0341(10) 0.0548(12) -0.0525(12) F9 0.0444(10) 0.0387(9) 0.0399(9) 0.0023(7) 0.0004(8) -0.0223(8) F10 0.0344(8) 0.0281(8) 0.0324(8) 0.0090(6) 0.0064(7) -0.0062(7) F11 0.0496(10) 0.0211(8) 0.0319(8) -0.0074(6) 0.0008(7) 0.0059(7) F12 0.0390(10) 0.0473(11) 0.0570(12) 0.0205(9) -0.0238(8) -0.0270(9) C11 0.0396(17) 0.097(3) 0.0421(17) -0.0401(18) 0.0202(14) -0.0433(19) F13 0.082(5) 0.118(8) 0.046(2) -0.034(3) 0.032(2) -0.078(5) F14 0.027(2) 0.139(5) 0.111(5) -0.071(4) 0.025(2) -0.039(3) F15 0.066(6) 0.120(5) 0.062(6) -0.050(4) 0.030(4) -0.074(4) C11' 0.0396(17) 0.097(3) 0.0421(17) -0.0401(18) 0.0202(14) -0.0433(19) F13' 0.072(9) 0.102(11) 0.041(5) -0.048(6) 0.041(5) -0.069(8) F14' 0.022(4) 0.089(8) 0.089(9) -0.042(6) 0.003(5) -0.028(4) F15' 0.037(6) 0.060(7) 0.045(8) -0.021(5) 0.006(5) -0.031(5) C15 0.073(3) 0.109(3) 0.0210(14) 0.0098(18) -0.0123(15) -0.073(3) F16 0.036(4) 0.058(4) 0.016(2) -0.002(2) -0.0073(18) -0.022(2) F17 0.058(3) 0.157(8) 0.0310(19) -0.008(3) -0.0009(17) -0.075(5) F18 0.164(9) 0.041(3) 0.075(5) 0.015(3) -0.080(5) -0.054(4) C15' 0.073(3) 0.109(3) 0.0210(14) 0.0098(18) -0.0123(15) -0.073(3) F16' 0.043(7) 0.046(5) 0.053(6) -0.007(3) -0.025(4) -0.009(4) F17' 0.060(4) 0.066(4) 0.028(2) -0.015(2) 0.010(2) -0.051(4) F18' 0.061(3) 0.034(3) 0.034(3) -0.005(2) -0.003(2) -0.028(2) O1 0.0317(9) 0.0174(8) 0.0207(8) -0.0045(6) 0.0025(7) 0.0012(7) O2 0.0312(9) 0.0157(8) 0.0255(9) -0.0060(7) 0.0018(7) -0.0026(7) O3 0.0378(10) 0.0178(8) 0.0240(9) -0.0008(7) 0.0108(7) -0.0053(7) O4 0.0237(8) 0.0172(8) 0.0224(8) -0.0012(6) 0.0035(6) -0.0046(6) O5 0.0254(8) 0.0214(8) 0.0225(8) -0.0071(7) 0.0014(7) -0.0048(7) O6 0.0270(9) 0.0217(8) 0.0212(8) -0.0026(7) 0.0040(7) -0.0070(7) C2 0.0199(10) 0.0144(10) 0.0242(11) -0.0035(8) 0.0070(9) -0.0072(8) C3 0.0192(11) 0.0186(11) 0.0434(15) -0.0120(10) -0.0021(10) -0.0037(9) C4 0.0172(10) 0.0150(10) 0.0347(13) -0.0070(9) 0.0067(9) -0.0062(8) C5 0.0211(12) 0.0233(14) 0.084(2) -0.0277(15) -0.0044(14) -0.0013(11) C6 0.0204(11) 0.0211(11) 0.0221(11) -0.0013(9) 0.0014(9) -0.0084(9) C7 0.0279(12) 0.0147(10) 0.0167(10) -0.0052(8) 0.0029(9) -0.0051(9) C8 0.0280(12) 0.0198(11) 0.0254(12) -0.0033(9) 0.0056(9) -0.0097(10) C9 0.0379(14) 0.0159(11) 0.0223(11) -0.0070(9) 0.0073(10) -0.0098(10) C10 0.0525(17) 0.0244(13) 0.0268(13) -0.0050(10) 0.0113(12) -0.0210(12) C12 0.0228(12) 0.0467(16) 0.0253(12) -0.0120(11) 0.0056(10) -0.0146(11) C13 0.061(2) 0.123(4) 0.0204(14) -0.0226(17) 0.0131(14) -0.068(2) C14 0.0291(13) 0.0508(17) 0.0200(12) -0.0014(11) -0.0033(10) -0.0196(12) N 0.0284(11) 0.0171(10) 0.0470(14) -0.0002(9) -0.0127(10) -0.0103(9) C16 0.0461(17) 0.0286(14) 0.0509(18) 0.0093(13) -0.0190(14) -0.0249(13) C17 0.057(2) 0.0433(18) 0.052(2) 0.0125(15) -0.0154(16) -0.0293(16) C18 0.0341(14) 0.0243(13) 0.0532(18) -0.0083(12) -0.0108(13) -0.0110(11) C19 0.0346(15) 0.0258(14) 0.060(2) -0.0076(13) -0.0031(14) -0.0063(12) C20 0.0306(14) 0.0295(15) 0.064(2) -0.0088(14) -0.0181(14) -0.0105(12) C21 0.046(2) 0.0407(19) 0.086(3) -0.0046(19) -0.033(2) 0.0016(16) C22 0.0318(14) 0.0175(12) 0.0481(17) 0.0018(11) 0.0010(12) -0.0067(10) C23 0.0256(14) 0.0397(17) 0.0534(19) 0.0141(14) 0.0014(13) -0.0012(12) _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 Ni O1 2.0306(17) . ? Ni O2 2.0284(17) . ? Ni O3 2.0366(18) . ? Ni O4 2.0303(16) . ? Ni O5 2.0334(18) . ? Ni O6 2.0279(17) . ? C1 F1 1.332(3) . ? C1 F2 1.327(3) . ? C1 F3 1.324(3) . ? C1 C2 1.538(3) . ? F4 C5 1.337(4) . ? F5 C5 1.330(4) . ? F6 C5 1.333(3) . ? F7 C10 1.325(3) . ? F8 C10 1.332(3) . ? F9 C10 1.333(3) . ? F10 C6 1.326(3) . ? F11 C6 1.329(3) . ? F12 C6 1.327(3) . ? C11 F13 1.336(7) . ? C11 F14 1.327(8) . ? C11 F15 1.323(7) . ? C11 C12 1.536(4) . ? C15 F16 1.334(8) . ? C15 F17 1.439(6) . ? C15 F18 1.171(7) . ? C15 C14 1.538(4) . ? O1 C2 1.241(3) . ? O2 C4 1.240(3) . ? O3 C9 1.244(3) . ? O4 C7 1.252(3) . ? O5 C12 1.235(3) . ? O6 C14 1.230(3) . ? C2 C3 1.394(3) . ? C3 H3 0.950 . ? C3 C4 1.388(3) . ? C4 C5 1.530(3) . ? C6 C7 1.535(3) . ? C7 C8 1.390(3) . ? C8 H8 0.950 . ? C8 C9 1.393(3) . ? C9 C10 1.539(4) . ? C12 C13 1.387(4) . ? C13 H13 0.950 . ? C13 C14 1.382(4) . ? N C16 1.514(4) . ? N C18 1.519(4) . ? N C20 1.513(3) . ? N C22 1.523(3) . ? C16 H16A 0.990 . ? C16 H16B 0.990 . ? C16 C17 1.505(5) . ? C17 H17A 0.980 . ? C17 H17B 0.980 . ? C17 H17C 0.980 . ? C18 H18A 0.990 . ? C18 H18B 0.990 . ? C18 C19 1.509(4) . ? C19 H19A 0.980 . ? C19 H19B 0.980 . ? C19 H19C 0.980 . ? C20 H20A 0.990 . ? C20 H20B 0.990 . ? C20 C21 1.517(4) . ? C21 H21A 0.980 . ? C21 H21B 0.980 . ? C21 H21C 0.980 . ? C22 H22A 0.990 . ? C22 H22B 0.990 . ? C22 C23 1.509(4) . ? C23 H23A 0.980 . ? C23 H23B 0.980 . ? C23 H23C 0.980 . ? 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 Ni O2 90.78(7) . . ? O1 Ni O3 90.81(7) . . ? O1 Ni O4 91.18(7) . . ? O1 Ni O5 90.63(7) . . ? O1 Ni O6 178.33(7) . . ? O2 Ni O3 91.13(7) . . ? O2 Ni O4 176.78(7) . . ? O2 Ni O5 88.11(7) . . ? O2 Ni O6 89.50(7) . . ? O3 Ni O4 91.39(7) . . ? O3 Ni O5 178.39(7) . . ? O3 Ni O6 87.54(7) . . ? O4 Ni O5 89.32(7) . . ? O4 Ni O6 88.61(7) . . ? O5 Ni O6 91.02(7) . . ? F1 C1 F2 106.7(2) . . ? F1 C1 F3 106.19(19) . . ? F1 C1 C2 110.43(19) . . ? F2 C1 F3 107.6(2) . . ? F2 C1 C2 113.27(19) . . ? F3 C1 C2 112.3(2) . . ? F13 C11 F14 109.4(7) . . ? F13 C11 F15 106.3(6) . . ? F13 C11 C12 112.8(5) . . ? F14 C11 F15 107.3(5) . . ? F14 C11 C12 108.4(7) . . ? F15 C11 C12 112.5(6) . . ? F16 C15 F17 97.4(7) . . ? F16 C15 F18 114.9(8) . . ? F16 C15 C14 110.3(7) . . ? F17 C15 F18 113.5(5) . . ? F17 C15 C14 104.5(3) . . ? F18 C15 C14 114.5(4) . . ? Ni O1 C2 123.61(15) . . ? Ni O2 C4 122.84(15) . . ? Ni O3 C9 121.99(16) . . ? Ni O4 C7 121.88(15) . . ? Ni O5 C12 123.61(17) . . ? Ni O6 C14 123.58(17) . . ? C1 C2 O1 114.91(19) . . ? C1 C2 C3 116.0(2) . . ? O1 C2 C3 129.1(2) . . ? C2 C3 H3 118.9 . . ? C2 C3 C4 122.3(2) . . ? H3 C3 C4 118.9 . . ? O2 C4 C3 129.5(2) . . ? O2 C4 C5 113.1(2) . . ? C3 C4 C5 117.5(2) . . ? F4 C5 F5 106.7(3) . . ? F4 C5 F6 106.8(3) . . ? F4 C5 C4 110.6(2) . . ? F5 C5 F6 107.6(3) . . ? F5 C5 C4 110.7(3) . . ? F6 C5 C4 114.1(2) . . ? F10 C6 F11 106.27(19) . . ? F10 C6 F12 107.4(2) . . ? F10 C6 C7 112.16(19) . . ? F11 C6 F12 107.2(2) . . ? F11 C6 C7 110.35(19) . . ? F12 C6 C7 113.1(2) . . ? O4 C7 C6 114.2(2) . . ? O4 C7 C8 129.1(2) . . ? C6 C7 C8 116.6(2) . . ? C7 C8 H8 118.6 . . ? C7 C8 C9 122.8(2) . . ? H8 C8 C9 118.6 . . ? O3 C9 C8 129.5(2) . . ? O3 C9 C10 115.7(2) . . ? C8 C9 C10 114.8(2) . . ? F7 C10 F8 107.9(2) . . ? F7 C10 F9 107.2(2) . . ? F7 C10 C9 112.4(2) . . ? F8 C10 F9 105.5(3) . . ? F8 C10 C9 111.7(2) . . ? F9 C10 C9 111.8(2) . . ? C11 C12 O5 113.4(2) . . ? C11 C12 C13 118.0(2) . . ? O5 C12 C13 128.6(3) . . ? C12 C13 H13 118.3 . . ? C12 C13 C14 123.5(3) . . ? H13 C13 C14 118.3 . . ? C15 C14 O6 114.2(2) . . ? C15 C14 C13 116.8(2) . . ? O6 C14 C13 129.0(3) . . ? C16 N C18 106.1(2) . . ? C16 N C20 111.3(2) . . ? C16 N C22 111.5(2) . . ? C18 N C20 111.2(2) . . ? C18 N C22 111.3(2) . . ? C20 N C22 105.5(2) . . ? N C16 H16A 108.4 . . ? N C16 H16B 108.4 . . ? N C16 C17 115.4(2) . . ? H16A C16 H16B 107.5 . . ? H16A C16 C17 108.4 . . ? H16B C16 C17 108.4 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17B 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N C18 H18A 108.3 . . ? N C18 H18B 108.3 . . ? N C18 C19 116.0(2) . . ? H18A C18 H18B 107.4 . . ? H18A C18 C19 108.3 . . ? H18B C18 C19 108.3 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19B 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N C20 H20A 108.5 . . ? N C20 H20B 108.5 . . ? N C20 C21 115.0(2) . . ? H20A C20 H20B 107.5 . . ? H20A C20 C21 108.5 . . ? H20B C20 C21 108.5 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21B 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? N C22 H22A 108.4 . . ? N C22 H22B 108.4 . . ? N C22 C23 115.4(2) . . ? H22A C22 H22B 107.5 . . ? H22A C22 C23 108.4 . . ? H22B C22 C23 108.4 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23B 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 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 Ni O1 C2 -9.22(19) . . . . ? O3 Ni O1 C2 -100.37(19) . . . . ? O4 Ni O1 C2 168.22(19) . . . . ? O5 Ni O1 C2 78.89(19) . . . . ? O6 Ni O1 C2 -109(2) . . . . ? O1 Ni O2 C4 15.07(19) . . . . ? O3 Ni O2 C4 105.89(19) . . . . ? O4 Ni O2 C4 -112.5(13) . . . . ? O5 Ni O2 C4 -75.53(19) . . . . ? O6 Ni O2 C4 -166.57(19) . . . . ? O1 Ni O3 C9 -107.20(19) . . . . ? O2 Ni O3 C9 162.01(19) . . . . ? O4 Ni O3 C9 -15.99(19) . . . . ? O5 Ni O3 C9 100(3) . . . . ? O6 Ni O3 C9 72.55(19) . . . . ? O1 Ni O4 C7 109.29(17) . . . . ? O2 Ni O4 C7 -123.1(13) . . . . ? O3 Ni O4 C7 18.45(18) . . . . ? O5 Ni O4 C7 -160.10(17) . . . . ? O6 Ni O4 C7 -69.05(17) . . . . ? O1 Ni O5 C12 177.1(2) . . . . ? O2 Ni O5 C12 -92.1(2) . . . . ? O3 Ni O5 C12 -30(3) . . . . ? O4 Ni O5 C12 86.0(2) . . . . ? O6 Ni O5 C12 -2.6(2) . . . . ? O1 Ni O6 C14 -165(2) . . . . ? O2 Ni O6 C14 95.5(2) . . . . ? O3 Ni O6 C14 -173.3(2) . . . . ? O4 Ni O6 C14 -81.9(2) . . . . ? O5 Ni O6 C14 7.4(2) . . . . ? Ni O1 C2 C1 178.27(14) . . . . ? Ni O1 C2 C3 1.0(4) . . . . ? F1 C1 C2 O1 -91.8(2) . . . . ? F1 C1 C2 C3 85.9(3) . . . . ? F2 C1 C2 O1 148.6(2) . . . . ? F2 C1 C2 C3 -33.7(3) . . . . ? F3 C1 C2 O1 26.5(3) . . . . ? F3 C1 C2 C3 -155.8(2) . . . . ? C1 C2 C3 C4 -171.0(2) . . . . ? O1 C2 C3 C4 6.3(4) . . . . ? Ni O2 C4 C3 -13.9(4) . . . . ? Ni O2 C4 C5 168.15(19) . . . . ? C2 C3 C4 O2 1.3(4) . . . . ? C2 C3 C4 C5 179.2(3) . . . . ? O2 C4 C5 F4 76.6(3) . . . . ? O2 C4 C5 F5 -41.4(3) . . . . ? O2 C4 C5 F6 -163.0(3) . . . . ? C3 C4 C5 F4 -101.6(3) . . . . ? C3 C4 C5 F5 140.4(3) . . . . ? C3 C4 C5 F6 18.8(4) . . . . ? Ni O4 C7 C6 171.16(14) . . . . ? Ni O4 C7 C8 -12.2(3) . . . . ? F10 C6 C7 O4 -29.9(3) . . . . ? F10 C6 C7 C8 153.0(2) . . . . ? F11 C6 C7 O4 88.4(2) . . . . ? F11 C6 C7 C8 -88.7(3) . . . . ? F12 C6 C7 O4 -151.5(2) . . . . ? F12 C6 C7 C8 31.4(3) . . . . ? O4 C7 C8 C9 -3.9(4) . . . . ? C6 C7 C8 C9 172.7(2) . . . . ? Ni O3 C9 C8 6.7(4) . . . . ? Ni O3 C9 C10 -174.42(15) . . . . ? C7 C8 C9 O3 7.2(4) . . . . ? C7 C8 C9 C10 -171.7(2) . . . . ? O3 C9 C10 F7 3.0(3) . . . . ? O3 C9 C10 F8 -118.4(3) . . . . ? O3 C9 C10 F9 123.6(3) . . . . ? C8 C9 C10 F7 -178.0(2) . . . . ? C8 C9 C10 F8 60.6(3) . . . . ? C8 C9 C10 F9 -57.4(3) . . . . ? Ni O5 C12 C11 175.7(2) . . . . ? Ni O5 C12 C13 -3.3(5) . . . . ? F13 C11 C12 O5 157.9(11) . . . . ? F13 C11 C12 C13 -23.0(12) . . . . ? F14 C11 C12 O5 -80.8(9) . . . . ? F14 C11 C12 C13 98.3(9) . . . . ? F15 C11 C12 O5 37.6(12) . . . . ? F15 C11 C12 C13 -143.3(12) . . . . ? C11 C12 C13 C14 -172.4(4) . . . . ? O5 C12 C13 C14 6.5(7) . . . . ? Ni O6 C14 C15 174.6(2) . . . . ? Ni O6 C14 C13 -7.1(5) . . . . ? C12 C13 C14 C15 177.8(4) . . . . ? C12 C13 C14 O6 -0.5(7) . . . . ? F16 C15 C14 O6 -140.5(7) . . . . ? F16 C15 C14 C13 40.9(8) . . . . ? F17 C15 C14 O6 -36.7(5) . . . . ? F17 C15 C14 C13 144.7(5) . . . . ? F18 C15 C14 O6 88.0(7) . . . . ? F18 C15 C14 C13 -90.5(7) . . . . ? C18 N C16 C17 -180.0(3) . . . . ? C20 N C16 C17 58.9(3) . . . . ? C22 N C16 C17 -58.6(3) . . . . ? C16 N C18 C19 -174.7(2) . . . . ? C20 N C18 C19 -53.4(3) . . . . ? C22 N C18 C19 63.8(3) . . . . ? C16 N C20 C21 61.0(4) . . . . ? C18 N C20 C21 -57.1(4) . . . . ? C22 N C20 C21 -177.9(3) . . . . ? C16 N C22 C23 -54.6(3) . . . . ? C18 N C22 C23 63.8(3) . . . . ? C20 N C22 C23 -175.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.853 _refine_diff_density_min -0.552 _refine_diff_density_rms 0.070 data_jtn103 _database_code_depnum_ccdc_archive 'CCDC 886193' #TrackingRef '11834_web_deposit_cif_file_2_JonT.Njardarson_1339529666.3_Znhfacac3NEt4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H20 N +, C15 H3 F18 O6 Zn -' _chemical_formula_sum 'C23 H23 F18 N O6 Zn' _chemical_formula_weight 816.79 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 '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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.3786(13) _cell_length_b 10.8425(14) _cell_length_c 15.1786(19) _cell_angle_alpha 86.056(2) _cell_angle_beta 80.156(2) _cell_angle_gamma 67.947(2) _cell_volume 1559.8(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9995 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 31.84 _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_max 1.12 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.739 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 0.934 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.4201 _exptl_absorpt_correction_T_max 0.8962 _exptl_absorpt_process_details 'SADABS; Sheldrick, 1996' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube with Miracol optics' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Kappa APEXII DUO CCD diffractometer' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 33132 _diffrn_reflns_av_R_equivalents 0.0319 _diffrn_reflns_av_sigmaI/netI 0.0374 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 33.14 _reflns_number_total 11353 _reflns_number_gt 8896 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 (Bruker, 2007)' _computing_cell_refinement 'SAINT (Bruker, 2007)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement SHELXTL _computing_molecular_graphics 'ORTEP3 for Windows (Farrugia, 1997)' _computing_publication_material 'SHELXTL and local programs' _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^)+(0.0513P)^2^+0.3996P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary heavy _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 11353 _refine_ls_number_parameters 483 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.0549 _refine_ls_R_factor_gt 0.0390 _refine_ls_wR_factor_ref 0.1042 _refine_ls_wR_factor_gt 0.0957 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn Zn 0.623216(16) 0.780877(16) 0.269972(11) 0.01899(5) Uani 1 1 d . . . F1 F 0.80611(13) 0.57505(11) -0.06150(6) 0.0378(2) Uani 1 1 d . . . F2 F 0.80551(13) 0.43593(10) 0.04682(7) 0.0386(2) Uani 1 1 d . . . F3 F 0.60966(12) 0.57243(13) 0.01179(8) 0.0443(3) Uani 1 1 d . . . F4 F 1.02291(12) 0.84717(13) 0.01850(7) 0.0416(3) Uani 1 1 d . . . F5 F 1.10919(10) 0.73108(11) 0.12935(8) 0.0404(3) Uani 1 1 d . . . F6 F 0.98121(11) 0.93818(11) 0.14692(8) 0.0377(3) Uani 1 1 d . . . F7 F 1.01696(14) 0.41522(13) 0.27472(9) 0.0558(4) Uani 1 1 d . . . F8 F 1.08441(10) 0.46663(10) 0.38880(8) 0.0362(2) Uani 1 1 d . . . F9 F 0.93416(13) 0.37045(11) 0.40671(10) 0.0474(3) Uani 1 1 d . . . F10 F 0.65318(11) 1.02880(10) 0.49949(7) 0.0336(2) Uani 1 1 d . . . F11 F 0.86332(11) 0.89765(12) 0.51181(9) 0.0476(3) Uani 1 1 d . . . F12 F 0.68714(16) 0.85740(12) 0.58432(7) 0.0492(3) Uani 1 1 d . . . C11 C 0.21518(16) 0.75040(17) 0.37210(11) 0.0258(3) Uani 1 1 d D . . F13 F 0.11108(12) 0.76043(14) 0.32856(8) 0.0506(3) Uani 1 1 d D . . F14 F 0.26931(11) 0.62460(11) 0.39916(8) 0.0360(2) Uani 1 1 d D . . F15 F 0.15938(13) 0.82358(12) 0.44608(8) 0.0445(3) Uani 1 1 d D . . C15 C 0.2910(5) 1.0920(6) 0.1537(4) 0.0361(11) Uani 0.728(9) 1 d PD A 1 F16 F 0.3733(2) 1.0896(4) 0.0786(2) 0.0656(13) Uani 0.728(9) 1 d PD A 1 F17 F 0.2727(3) 1.2016(3) 0.1965(3) 0.0627(9) Uani 0.728(9) 1 d PD A 1 F18 F 0.1677(4) 1.0992(4) 0.1378(3) 0.0660(13) Uani 0.728(9) 1 d PD A 1 C15' C 0.2978(17) 1.0664(16) 0.1425(11) 0.039(4) Uani 0.272(9) 1 d PD A 2 F16' F 0.334(2) 1.0245(10) 0.0600(5) 0.150(7) Uani 0.272(9) 1 d PD A 2 F17' F 0.3265(13) 1.1773(11) 0.1413(11) 0.095(6) Uani 0.272(9) 1 d PD A 2 F18' F 0.1592(11) 1.1230(15) 0.1542(11) 0.092(5) Uani 0.272(9) 1 d PD A 2 O1 O 0.64118(11) 0.67852(11) 0.15420(7) 0.0220(2) Uani 1 1 d . . . O2 O 0.79222(11) 0.83348(11) 0.20671(7) 0.0229(2) Uani 1 1 d . . . O3 O 0.76213(11) 0.60136(11) 0.31159(8) 0.0246(2) Uani 1 1 d . . . O4 O 0.63764(11) 0.86750(11) 0.38452(7) 0.0235(2) Uani 1 1 d . . . O5 O 0.44953(11) 0.73916(11) 0.33258(7) 0.0220(2) Uani 1 1 d . . . O6 O 0.48591(11) 0.95000(11) 0.21717(8) 0.0236(2) Uani 1 1 d . A . C1 C 0.73936(18) 0.56180(17) 0.01964(11) 0.0276(3) Uani 1 1 d . . . C2 C 0.73757(15) 0.65945(14) 0.08884(10) 0.0200(3) Uani 1 1 d . . . C3 C 0.84618(16) 0.70921(16) 0.07224(10) 0.0236(3) Uani 1 1 d . . . H3 H 0.9096 0.6871 0.0175 0.028 Uiso 1 1 calc R . . C4 C 0.86477(14) 0.78976(14) 0.13280(10) 0.0199(3) Uani 1 1 d . . . C5 C 0.99514(16) 0.82775(16) 0.10627(11) 0.0256(3) Uani 1 1 d . . . C6 C 0.97367(18) 0.46164(16) 0.35725(12) 0.0297(3) Uani 1 1 d . . . C7 C 0.84954(15) 0.59601(15) 0.36104(10) 0.0217(3) Uani 1 1 d . . . C8 C 0.84536(15) 0.69146(15) 0.41907(10) 0.0234(3) Uani 1 1 d . . . H8 H 0.9193 0.6712 0.4534 0.028 Uiso 1 1 calc R . . C9 C 0.73604(15) 0.81662(15) 0.42891(10) 0.0207(3) Uani 1 1 d . . . C10 C 0.73540(16) 0.90165(16) 0.50624(11) 0.0249(3) Uani 1 1 d . . . C12 C 0.32695(14) 0.79698(15) 0.31552(10) 0.0205(3) Uani 1 1 d . . . C13 C 0.27699(15) 0.90116(16) 0.25569(11) 0.0248(3) Uani 1 1 d . A . H13 H 0.1831 0.9269 0.2444 0.030 Uiso 1 1 calc R . . C14 C 0.36083(16) 0.96853(15) 0.21195(11) 0.0238(3) Uani 1 1 d . . . N N 0.62180(13) 0.28169(12) 0.26632(8) 0.0220(2) Uani 1 1 d . . . C16 C 0.60888(18) 0.17420(16) 0.21366(12) 0.0293(3) Uani 1 1 d . . . H16A H 0.6600 0.0868 0.2398 0.035 Uiso 1 1 calc R . . H16B H 0.5083 0.1858 0.2216 0.035 Uiso 1 1 calc R . . C17 C 0.6633(2) 0.1705(2) 0.11503(14) 0.0447(5) Uani 1 1 d . . . H17A H 0.6097 0.2542 0.0872 0.067 Uiso 1 1 calc R . . H17B H 0.6525 0.0962 0.0878 0.067 Uiso 1 1 calc R . . H17C H 0.7630 0.1585 0.1058 0.067 Uiso 1 1 calc R . . C18 C 0.77509(18) 0.25878(18) 0.26747(13) 0.0336(4) Uani 1 1 d . . . H18A H 0.8238 0.2527 0.2049 0.040 Uiso 1 1 calc R . . H18B H 0.7793 0.3373 0.2947 0.040 Uiso 1 1 calc R . . C19 C 0.85456(19) 0.1352(2) 0.31765(14) 0.0381(4) Uani 1 1 d . . . H19A H 0.8136 0.1441 0.3811 0.057 Uiso 1 1 calc R . . H19B H 0.9537 0.1248 0.3111 0.057 Uiso 1 1 calc R . . H19C H 0.8477 0.0570 0.2931 0.057 Uiso 1 1 calc R . . C20 C 0.54494(19) 0.27577(19) 0.35962(11) 0.0342(4) Uani 1 1 d . . . H20A H 0.5824 0.1832 0.3821 0.041 Uiso 1 1 calc R . . H20B H 0.4441 0.2985 0.3563 0.041 Uiso 1 1 calc R . . C21 C 0.5565(3) 0.3678(2) 0.42650(14) 0.0531(6) Uani 1 1 d . . . H21A H 0.6557 0.3449 0.4316 0.080 Uiso 1 1 calc R . . H21B H 0.5043 0.3578 0.4850 0.080 Uiso 1 1 calc R . . H21C H 0.5169 0.4602 0.4060 0.080 Uiso 1 1 calc R . . C22 C 0.55755(19) 0.41850(16) 0.22491(12) 0.0312(3) Uani 1 1 d . . . H22A H 0.5629 0.4855 0.2638 0.037 Uiso 1 1 calc R . . H22B H 0.6157 0.4214 0.1664 0.037 Uiso 1 1 calc R . . C23 C 0.4066(2) 0.45843(19) 0.21065(13) 0.0383(4) Uani 1 1 d . . . H23A H 0.3993 0.3928 0.1724 0.057 Uiso 1 1 calc R . . H23B H 0.3761 0.5461 0.1818 0.057 Uiso 1 1 calc R . . H23C H 0.3465 0.4623 0.2685 0.057 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 Zn 0.01420(8) 0.02112(9) 0.02339(9) -0.00023(6) -0.00505(6) -0.00760(6) F1 0.0542(7) 0.0480(6) 0.0211(5) -0.0033(4) -0.0018(4) -0.0314(6) F2 0.0540(7) 0.0255(5) 0.0368(6) -0.0054(4) 0.0012(5) -0.0180(5) F3 0.0381(6) 0.0683(8) 0.0406(6) -0.0144(6) -0.0105(5) -0.0313(6) F4 0.0461(7) 0.0602(7) 0.0323(5) 0.0010(5) 0.0022(5) -0.0390(6) F5 0.0176(4) 0.0427(6) 0.0612(7) -0.0035(5) -0.0096(5) -0.0096(4) F6 0.0305(5) 0.0377(6) 0.0522(7) -0.0162(5) 0.0054(5) -0.0231(5) F7 0.0434(7) 0.0531(8) 0.0479(7) -0.0184(6) -0.0148(6) 0.0146(6) F8 0.0211(5) 0.0288(5) 0.0603(7) 0.0019(5) -0.0181(5) -0.0064(4) F9 0.0420(6) 0.0271(5) 0.0825(9) 0.0165(6) -0.0328(6) -0.0165(5) F10 0.0365(5) 0.0269(5) 0.0354(5) -0.0053(4) -0.0108(4) -0.0063(4) F11 0.0241(5) 0.0518(7) 0.0716(8) -0.0292(6) -0.0144(5) -0.0112(5) F12 0.0857(10) 0.0495(7) 0.0227(5) 0.0007(5) -0.0031(6) -0.0391(7) C11 0.0199(7) 0.0332(8) 0.0288(7) 0.0012(6) -0.0043(6) -0.0148(6) F13 0.0366(6) 0.0859(10) 0.0514(7) 0.0270(7) -0.0222(5) -0.0458(7) F14 0.0333(5) 0.0336(5) 0.0456(6) 0.0072(5) -0.0025(5) -0.0201(4) F15 0.0426(6) 0.0462(7) 0.0427(6) -0.0130(5) 0.0174(5) -0.0222(5) C15 0.0219(15) 0.028(2) 0.061(3) 0.0226(18) -0.0188(15) -0.0107(13) F16 0.0457(12) 0.078(2) 0.0516(16) 0.0391(15) -0.0054(10) -0.0064(12) F17 0.0520(14) 0.0269(10) 0.105(2) 0.0182(12) -0.0276(15) -0.0065(9) F18 0.048(2) 0.073(2) 0.106(3) 0.062(2) -0.061(2) -0.0444(19) C15' 0.040(6) 0.024(6) 0.061(7) 0.005(4) -0.016(5) -0.020(5) F16' 0.290(15) 0.058(5) 0.038(3) 0.002(3) -0.070(6) 0.027(7) F17' 0.091(9) 0.078(7) 0.173(14) 0.093(9) -0.108(10) -0.072(7) F18' 0.033(4) 0.090(7) 0.099(7) 0.048(5) 0.004(4) 0.024(4) O1 0.0202(5) 0.0248(5) 0.0244(5) -0.0015(4) -0.0048(4) -0.0114(4) O2 0.0183(5) 0.0253(5) 0.0279(5) -0.0035(4) -0.0030(4) -0.0109(4) O3 0.0211(5) 0.0235(5) 0.0318(6) -0.0003(4) -0.0111(4) -0.0080(4) O4 0.0171(5) 0.0273(5) 0.0261(5) -0.0029(4) -0.0057(4) -0.0069(4) O5 0.0171(5) 0.0256(5) 0.0256(5) 0.0029(4) -0.0061(4) -0.0098(4) O6 0.0177(5) 0.0233(5) 0.0330(6) 0.0038(4) -0.0077(4) -0.0102(4) C1 0.0316(8) 0.0329(8) 0.0243(7) -0.0021(6) -0.0051(6) -0.0182(7) C2 0.0205(6) 0.0189(6) 0.0228(6) 0.0025(5) -0.0088(5) -0.0078(5) C3 0.0224(7) 0.0269(7) 0.0245(7) -0.0015(5) -0.0024(5) -0.0128(6) C4 0.0151(6) 0.0197(6) 0.0262(7) 0.0018(5) -0.0060(5) -0.0073(5) C5 0.0204(7) 0.0290(8) 0.0301(8) -0.0045(6) -0.0009(6) -0.0128(6) C6 0.0263(8) 0.0253(8) 0.0381(9) -0.0003(6) -0.0141(7) -0.0063(6) C7 0.0171(6) 0.0212(7) 0.0271(7) 0.0034(5) -0.0061(5) -0.0069(5) C8 0.0202(6) 0.0249(7) 0.0276(7) 0.0015(5) -0.0091(5) -0.0092(5) C9 0.0175(6) 0.0255(7) 0.0219(6) 0.0005(5) -0.0033(5) -0.0112(5) C10 0.0223(7) 0.0276(7) 0.0274(7) -0.0004(6) -0.0063(6) -0.0111(6) C12 0.0166(6) 0.0253(7) 0.0233(6) -0.0021(5) -0.0034(5) -0.0114(5) C13 0.0167(6) 0.0267(7) 0.0340(8) 0.0037(6) -0.0086(6) -0.0102(5) C14 0.0200(6) 0.0230(7) 0.0307(7) 0.0048(6) -0.0091(6) -0.0091(5) N 0.0230(6) 0.0214(6) 0.0253(6) 0.0008(5) -0.0056(5) -0.0116(5) C16 0.0327(8) 0.0243(7) 0.0367(9) -0.0026(6) -0.0112(7) -0.0142(6) C17 0.0472(12) 0.0422(11) 0.0361(10) -0.0120(8) -0.0091(9) -0.0038(9) C18 0.0252(8) 0.0357(9) 0.0467(10) -0.0015(7) -0.0082(7) -0.0177(7) C19 0.0271(8) 0.0395(10) 0.0440(10) -0.0080(8) -0.0109(7) -0.0047(7) C20 0.0311(8) 0.0398(10) 0.0256(8) 0.0071(7) -0.0031(6) -0.0082(7) C21 0.0505(13) 0.0569(14) 0.0313(10) -0.0122(9) -0.0150(9) 0.0091(10) C22 0.0391(9) 0.0219(7) 0.0357(9) 0.0054(6) -0.0118(7) -0.0133(7) C23 0.0438(10) 0.0300(9) 0.0364(9) -0.0014(7) -0.0179(8) -0.0031(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn O1 2.0869(11) . ? Zn O2 2.1033(10) . ? Zn O3 2.0739(11) . ? Zn O4 2.0848(11) . ? Zn O5 2.0796(10) . ? Zn O6 2.0644(11) . ? F1 C1 1.3327(19) . ? F2 C1 1.349(2) . ? F3 C1 1.3327(19) . ? F4 C5 1.3334(19) . ? F5 C5 1.3350(19) . ? F6 C5 1.3327(18) . ? F7 C6 1.323(2) . ? F8 C6 1.3385(18) . ? F9 C6 1.344(2) . ? F10 C10 1.3290(19) . ? F11 C10 1.3291(17) . ? F12 C10 1.3361(19) . ? C11 F13 1.3273(18) . ? C11 F14 1.3309(19) . ? C11 F15 1.335(2) . ? C11 C12 1.542(2) . ? C15 F16 1.298(6) . ? C15 F17 1.329(7) . ? C15 F18 1.315(5) . ? C15 C14 1.558(6) . ? C15' F16' 1.306(14) . ? C15' F17' 1.342(14) . ? C15' F18' 1.320(14) . ? C15' C14 1.492(19) . ? O1 C2 1.2495(18) . ? O2 C4 1.2515(18) . ? O3 C7 1.2557(17) . ? O4 C9 1.2500(17) . ? O5 C12 1.2530(17) . ? O6 C14 1.2526(17) . ? C1 C2 1.535(2) . ? C2 C3 1.4022(19) . ? C3 H3 0.950 . ? C3 C4 1.394(2) . ? C4 C5 1.540(2) . ? C6 C7 1.537(2) . ? C7 C8 1.388(2) . ? C8 H8 0.950 . ? C8 C9 1.402(2) . ? C9 C10 1.539(2) . ? C12 C13 1.396(2) . ? C13 H13 0.950 . ? C13 C14 1.394(2) . ? N C16 1.5156(19) . ? N C18 1.518(2) . ? N C20 1.512(2) . ? N C22 1.521(2) . ? C16 H16A 0.990 . ? C16 H16B 0.990 . ? C16 C17 1.505(3) . ? C17 H17A 0.980 . ? C17 H17B 0.980 . ? C17 H17C 0.980 . ? C18 H18A 0.990 . ? C18 H18B 0.990 . ? C18 C19 1.517(3) . ? C19 H19A 0.980 . ? C19 H19B 0.980 . ? C19 H19C 0.980 . ? C20 H20A 0.990 . ? C20 H20B 0.990 . ? C20 C21 1.521(3) . ? C21 H21A 0.980 . ? C21 H21B 0.980 . ? C21 H21C 0.980 . ? C22 H22A 0.990 . ? C22 H22B 0.990 . ? C22 C23 1.510(3) . ? C23 H23A 0.980 . ? C23 H23B 0.980 . ? C23 H23C 0.980 . ? 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 Zn O2 88.21(4) . . ? O1 Zn O3 85.29(4) . . ? O1 Zn O4 171.41(4) . . ? O1 Zn O5 93.05(4) . . ? O1 Zn O6 89.04(4) . . ? O2 Zn O3 90.72(4) . . ? O2 Zn O4 86.31(4) . . ? O2 Zn O5 177.06(4) . . ? O2 Zn O6 89.22(4) . . ? O3 Zn O4 88.17(4) . . ? O3 Zn O5 92.03(4) . . ? O3 Zn O6 174.33(4) . . ? O4 Zn O5 92.74(4) . . ? O4 Zn O6 97.49(4) . . ? O5 Zn O6 88.15(4) . . ? F13 C11 F14 107.29(13) . . ? F13 C11 F15 107.93(14) . . ? F13 C11 C12 112.70(13) . . ? F14 C11 F15 106.29(13) . . ? F14 C11 C12 112.45(13) . . ? F15 C11 C12 109.88(12) . . ? F16 C15 F17 107.3(4) . . ? F16 C15 F18 109.7(5) . . ? F16 C15 C14 110.2(4) . . ? F17 C15 F18 108.3(5) . . ? F17 C15 C14 108.9(4) . . ? F18 C15 C14 112.3(4) . . ? F16' C15' F17' 105.3(14) . . ? F16' C15' F18' 105.0(15) . . ? F16' C15' C14 116.5(11) . . ? F17' C15' F18' 98.0(13) . . ? F17' C15' C14 113.0(11) . . ? F18' C15' C14 116.9(13) . . ? Zn O1 C2 125.03(9) . . ? Zn O2 C4 124.84(9) . . ? Zn O3 C7 122.02(10) . . ? Zn O4 C9 123.38(10) . . ? Zn O5 C12 124.54(9) . . ? Zn O6 C14 124.28(9) . . ? F1 C1 F2 106.90(14) . . ? F1 C1 F3 108.15(13) . . ? F1 C1 C2 113.96(12) . . ? F2 C1 F3 106.34(13) . . ? F2 C1 C2 109.42(13) . . ? F3 C1 C2 111.68(14) . . ? O1 C2 C1 114.16(12) . . ? O1 C2 C3 129.47(14) . . ? C1 C2 C3 116.31(13) . . ? C2 C3 H3 118.7 . . ? C2 C3 C4 122.62(14) . . ? H3 C3 C4 118.7 . . ? O2 C4 C3 129.24(13) . . ? O2 C4 C5 115.21(12) . . ? C3 C4 C5 115.53(13) . . ? F4 C5 F5 106.89(13) . . ? F4 C5 F6 107.38(13) . . ? F4 C5 C4 112.72(12) . . ? F5 C5 F6 107.01(13) . . ? F5 C5 C4 110.43(13) . . ? F6 C5 C4 112.09(13) . . ? F7 C6 F8 108.08(15) . . ? F7 C6 F9 106.73(15) . . ? F7 C6 C7 111.41(14) . . ? F8 C6 F9 106.67(13) . . ? F8 C6 C7 113.42(13) . . ? F9 C6 C7 110.20(14) . . ? O3 C7 C6 113.43(13) . . ? O3 C7 C8 128.95(14) . . ? C6 C7 C8 117.58(13) . . ? C7 C8 H8 118.8 . . ? C7 C8 C9 122.41(13) . . ? H8 C8 C9 118.8 . . ? O4 C9 C8 128.83(14) . . ? O4 C9 C10 115.65(13) . . ? C8 C9 C10 115.50(13) . . ? F10 C10 F11 107.37(13) . . ? F10 C10 F12 106.67(13) . . ? F10 C10 C9 112.76(13) . . ? F11 C10 F12 107.01(14) . . ? F11 C10 C9 112.36(13) . . ? F12 C10 C9 110.33(12) . . ? C11 C12 O5 114.96(13) . . ? C11 C12 C13 115.90(13) . . ? O5 C12 C13 129.07(13) . . ? C12 C13 H13 119.0 . . ? C12 C13 C14 121.94(13) . . ? H13 C13 C14 119.0 . . ? C15 C14 O6 112.9(2) . . ? C15 C14 C13 117.9(2) . . ? C15' C14 O6 115.4(6) . . ? C15' C14 C13 115.3(6) . . ? O6 C14 C13 128.96(14) . . ? C16 N C18 111.06(13) . . ? C16 N C20 105.99(12) . . ? C16 N C22 111.53(12) . . ? C18 N C20 111.30(13) . . ? C18 N C22 106.41(12) . . ? C20 N C22 110.63(13) . . ? N C16 H16A 108.3 . . ? N C16 H16B 108.3 . . ? N C16 C17 116.08(14) . . ? H16A C16 H16B 107.4 . . ? H16A C16 C17 108.3 . . ? H16B C16 C17 108.3 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17B 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N C18 H18A 108.5 . . ? N C18 H18B 108.5 . . ? N C18 C19 115.08(14) . . ? H18A C18 H18B 107.5 . . ? H18A C18 C19 108.5 . . ? H18B C18 C19 108.5 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19B 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N C20 H20A 108.6 . . ? N C20 H20B 108.6 . . ? N C20 C21 114.66(16) . . ? H20A C20 H20B 107.6 . . ? H20A C20 C21 108.6 . . ? H20B C20 C21 108.6 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21B 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? N C22 H22A 108.4 . . ? N C22 H22B 108.4 . . ? N C22 C23 115.64(14) . . ? H22A C22 H22B 107.4 . . ? H22A C22 C23 108.4 . . ? H22B C22 C23 108.4 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23B 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 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 Zn O1 C2 7.39(12) . . . . ? O3 Zn O1 C2 -83.48(12) . . . . ? O4 Zn O1 C2 -43.0(3) . . . . ? O5 Zn O1 C2 -175.27(12) . . . . ? O6 Zn O1 C2 96.64(12) . . . . ? O1 Zn O2 C4 -7.34(12) . . . . ? O3 Zn O2 C4 77.92(12) . . . . ? O4 Zn O2 C4 166.04(12) . . . . ? O5 Zn O2 C4 -122.6(8) . . . . ? O6 Zn O2 C4 -96.41(12) . . . . ? O1 Zn O3 C7 148.11(12) . . . . ? O2 Zn O3 C7 59.97(12) . . . . ? O4 Zn O3 C7 -26.31(12) . . . . ? O5 Zn O3 C7 -118.99(12) . . . . ? O6 Zn O3 C7 149.3(4) . . . . ? O1 Zn O4 C9 -21.2(3) . . . . ? O2 Zn O4 C9 -71.66(11) . . . . ? O3 Zn O4 C9 19.18(11) . . . . ? O5 Zn O4 C9 111.13(11) . . . . ? O6 Zn O4 C9 -160.38(11) . . . . ? O1 Zn O5 C12 -76.75(12) . . . . ? O2 Zn O5 C12 38.4(8) . . . . ? O3 Zn O5 C12 -162.14(12) . . . . ? O4 Zn O5 C12 109.60(12) . . . . ? O6 Zn O5 C12 12.19(12) . . . . ? O1 Zn O6 C14 74.60(13) . . . . ? O2 Zn O6 C14 162.81(13) . . . . ? O3 Zn O6 C14 73.4(4) . . . . ? O4 Zn O6 C14 -111.01(13) . . . . ? O5 Zn O6 C14 -18.48(13) . . . . ? Zn O1 C2 C1 170.27(10) . . . . ? Zn O1 C2 C3 -6.5(2) . . . . ? F1 C1 C2 O1 158.09(14) . . . . ? F1 C1 C2 C3 -24.7(2) . . . . ? F2 C1 C2 O1 -82.31(16) . . . . ? F2 C1 C2 C3 94.92(16) . . . . ? F3 C1 C2 O1 35.16(19) . . . . ? F3 C1 C2 C3 -147.61(14) . . . . ? O1 C2 C3 C4 2.2(3) . . . . ? C1 C2 C3 C4 -174.51(14) . . . . ? Zn O2 C4 C3 6.4(2) . . . . ? Zn O2 C4 C5 -171.96(10) . . . . ? C2 C3 C4 O2 -2.2(3) . . . . ? C2 C3 C4 C5 176.17(14) . . . . ? O2 C4 C5 F4 -145.36(14) . . . . ? O2 C4 C5 F5 95.16(16) . . . . ? O2 C4 C5 F6 -24.05(19) . . . . ? C3 C4 C5 F4 36.07(19) . . . . ? C3 C4 C5 F5 -83.41(17) . . . . ? C3 C4 C5 F6 157.37(14) . . . . ? Zn O3 C7 C6 -159.58(10) . . . . ? Zn O3 C7 C8 22.9(2) . . . . ? F7 C6 C7 O3 40.22(19) . . . . ? F7 C6 C7 C8 -141.97(15) . . . . ? F8 C6 C7 O3 162.44(14) . . . . ? F8 C6 C7 C8 -19.8(2) . . . . ? F9 C6 C7 O3 -78.05(17) . . . . ? F9 C6 C7 C8 99.76(16) . . . . ? O3 C7 C8 C9 -1.6(3) . . . . ? C6 C7 C8 C9 -179.02(14) . . . . ? Zn O4 C9 C8 -6.9(2) . . . . ? Zn O4 C9 C10 174.61(9) . . . . ? C7 C8 C9 O4 -7.8(2) . . . . ? C7 C8 C9 C10 170.77(13) . . . . ? O4 C9 C10 F10 -16.79(18) . . . . ? O4 C9 C10 F11 -138.30(14) . . . . ? O4 C9 C10 F12 102.37(16) . . . . ? C8 C9 C10 F10 164.48(13) . . . . ? C8 C9 C10 F11 42.96(18) . . . . ? C8 C9 C10 F12 -76.36(17) . . . . ? Zn O5 C12 C11 -178.90(9) . . . . ? Zn O5 C12 C13 -2.2(2) . . . . ? F13 C11 C12 O5 -149.45(15) . . . . ? F13 C11 C12 C13 33.4(2) . . . . ? F14 C11 C12 O5 -28.02(19) . . . . ? F14 C11 C12 C13 154.79(14) . . . . ? F15 C11 C12 O5 90.15(16) . . . . ? F15 C11 C12 C13 -87.03(17) . . . . ? C11 C12 C13 C14 168.60(15) . . . . ? O5 C12 C13 C14 -8.1(3) . . . . ? Zn O6 C14 C15 -169.3(3) . . . . ? Zn O6 C14 C15' -157.0(6) . . . . ? Zn O6 C14 C13 16.0(2) . . . . ? C12 C13 C14 C15 -174.2(3) . . . . ? C12 C13 C14 C15' 173.2(6) . . . . ? C12 C13 C14 O6 0.3(3) . . . . ? F16' C15' C14 O6 77.7(14) . . . . ? F16' C15' C14 C13 -96.2(14) . . . . ? F17' C15' C14 O6 -44.4(14) . . . . ? F17' C15' C14 C13 141.6(12) . . . . ? F18' C15' C14 O6 -157.1(12) . . . . ? F18' C15' C14 C13 28.9(15) . . . . ? F16 C15 C14 O6 48.0(5) . . . . ? F16 C15 C14 C13 -136.7(3) . . . . ? F17 C15 C14 O6 -69.5(4) . . . . ? F17 C15 C14 C13 105.9(3) . . . . ? F18 C15 C14 O6 170.6(4) . . . . ? F18 C15 C14 C13 -14.0(6) . . . . ? C18 N C16 C17 -65.76(19) . . . . ? C20 N C16 C17 173.23(15) . . . . ? C22 N C16 C17 52.76(19) . . . . ? C16 N C18 C19 -66.29(19) . . . . ? C20 N C18 C19 51.54(19) . . . . ? C22 N C18 C19 172.15(15) . . . . ? C16 N C20 C21 174.61(15) . . . . ? C18 N C20 C21 53.75(19) . . . . ? C22 N C20 C21 -64.34(18) . . . . ? C16 N C22 C23 54.38(19) . . . . ? C18 N C22 C23 175.64(15) . . . . ? C20 N C22 C23 -63.32(18) . . . . ? _diffrn_measured_fraction_theta_max 0.955 _diffrn_reflns_theta_full 29.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.628 _refine_diff_density_min -0.739 _refine_diff_density_rms 0.072 data_mo_jn201b_0m _database_code_depnum_ccdc_archive 'CCDC 886194' #TrackingRef '11835_web_deposit_cif_file_3_JonT.Njardarson_1339529666.4_Cuhfacac2-2_complex.cif' _audit_creation_date 2011-09-25 _audit_creation_method ; Olex2 1.1 (compiled 2011.09.07 svn.r1971, GUI svn.r3853) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C21 H15 Cu F12 N O6 S' _chemical_formula_sum 'C21 H15 Cu F12 N O6 S' _chemical_formula_weight 700.94 _chemical_melting_point ? 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' 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' S S 0.1246 0.1234 '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' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 11.5841(3) _cell_length_b 12.0774(4) _cell_length_c 12.1591(3) _cell_angle_alpha 63.8590(10) _cell_angle_beta 71.4250(10) _cell_angle_gamma 64.5010(10) _cell_volume 1360.83(7) _cell_formula_units_Z 2 _cell_measurement_reflns_used 8292 _cell_measurement_temperature 200(2) _cell_measurement_theta_max 25.22 _cell_measurement_theta_min 2.51 _exptl_absorpt_coefficient_mu 0.999 _exptl_absorpt_correction_T_max 0.7452 _exptl_absorpt_correction_T_min 0.6583 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2008/1 (Bruker,2008) was used for absorption correction. R(int) was 0.0532 before and 0.0416 after correction. The Ratio of minimum to maximum transmission is 0.8834. The \l/2 correction factor is 0.0015. ; _exptl_crystal_colour green _exptl_crystal_colour_primary green _exptl_crystal_density_diffrn 1.711 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description ? _exptl_crystal_F_000 698 _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.05 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0282 _diffrn_reflns_av_unetI/netI 0.0211 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 25131 _diffrn_reflns_theta_full 25.29 _diffrn_reflns_theta_max 25.29 _diffrn_reflns_theta_min 1.89 _diffrn_ambient_temperature 199.98 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_current 30.0 _diffrn_source_power 1.5 _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _reflns_number_gt 4179 _reflns_number_total 4948 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ? _computing_data_collection ? _computing_data_reduction 'SAINT v7.68A (Bruker, 2009)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _refine_diff_density_max 0.653 _refine_diff_density_min -0.384 _refine_diff_density_rms 0.058 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.129 _refine_ls_hydrogen_treatment noref _refine_ls_matrix_type full _refine_ls_number_parameters 411 _refine_ls_number_reflns 4948 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.0462 _refine_ls_R_factor_gt 0.0376 _refine_ls_restrained_S_all 1.128 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1310 _refine_ls_wR_factor_ref 0.1406 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.5000 0.0000 0.5000 0.03176(16) Uani 1 2 d S . . Cu2 Cu 0.5000 0.5000 0.0000 0.03720(17) Uani 1 2 d S . . S1 S 0.43125(6) 0.35272(6) 0.35543(6) 0.03432(19) Uani 1 1 d . . . O5 O 0.62841(17) -0.02242(18) 0.58484(17) 0.0364(4) Uani 1 1 d . . . O4 O 0.48367(19) 0.3853(2) -0.06065(18) 0.0420(5) Uani 1 1 d . . . C18 C 0.6058(3) -0.0266(3) 0.6947(3) 0.0370(6) Uani 1 1 d . . . F1 F 0.8034(2) 0.0104(3) 0.6484(2) 0.0754(7) Uani 1 1 d . . . O1 O 0.4474(2) 0.3622(2) 0.23034(19) 0.0458(5) Uani 1 1 d . . . O2 O 0.4231(2) 0.23117(18) 0.4525(2) 0.0483(5) Uani 1 1 d . . . N1 N 0.5513(2) 0.3887(2) 0.3616(2) 0.0401(5) Uani 1 1 d . . . C2 C 0.6717(3) 0.2708(3) 0.3979(3) 0.0444(7) Uani 1 1 d . . . H2 H 0.6660 0.1840 0.4159 0.053 Uiso 1 1 calc R . . C5 C 0.2949(3) 0.4787(3) 0.3895(3) 0.0337(6) Uani 1 1 d . . . C10 C 0.2147(3) 0.4511(3) 0.5021(3) 0.0488(7) Uani 1 1 d . . . H10 H 0.2335 0.3642 0.5610 0.059 Uiso 1 1 calc R . . C6 C 0.2675(3) 0.6058(3) 0.3028(3) 0.0423(7) Uani 1 1 d . . . H6 H 0.3224 0.6253 0.2251 0.051 Uiso 1 1 calc R . . C8 C 0.0769(3) 0.6775(3) 0.4447(3) 0.0510(8) Uani 1 1 d . . . C9 C 0.1074(3) 0.5505(4) 0.5283(3) 0.0582(9) Uani 1 1 d . . . H9 H 0.0527 0.5311 0.6062 0.070 Uiso 1 1 calc R . . C7 C 0.1589(3) 0.7027(3) 0.3325(3) 0.0498(8) Uani 1 1 d . . . H7 H 0.1397 0.7898 0.2739 0.060 Uiso 1 1 calc R . . C1 C 0.5881(3) 0.3370(4) 0.4853(3) 0.0563(8) Uani 1 1 d . . . H1A H 0.6212 0.3898 0.5028 0.068 Uiso 1 1 calc R . . H1B H 0.5349 0.2908 0.5572 0.068 Uiso 1 1 calc R . . C3 C 0.7944(3) 0.2903(4) 0.3256(4) 0.0606(9) Uani 1 1 d . . . H3 H 0.8034 0.3724 0.3036 0.073 Uiso 1 1 calc R . . C11 C -0.0437(4) 0.7856(5) 0.4731(4) 0.0786(13) Uani 1 1 d . . . H11A H -0.1124 0.7491 0.5243 0.118 Uiso 1 1 calc R . . H11B H -0.0725 0.8536 0.3953 0.118 Uiso 1 1 calc R . . H11C H -0.0241 0.8241 0.5181 0.118 Uiso 1 1 calc R . . C4 C 0.8901(4) 0.2002(5) 0.2911(4) 0.0920(15) Uani 1 1 d . . . H4A H 0.8828 0.1175 0.3123 0.110 Uiso 1 1 calc R . . H4B H 0.9680 0.2163 0.2444 0.110 Uiso 1 1 calc R . . O3 O 0.31478(19) 0.5887(2) 0.02559(18) 0.0432(5) Uani 1 1 d . . . C14 C 0.2333(3) 0.5543(3) 0.0142(3) 0.0450(7) Uani 1 1 d . A . C12 C 0.3783(3) 0.3860(3) -0.0688(3) 0.0430(7) Uani 1 1 d . A . C16 C 0.3939(4) 0.2912(3) -0.1290(3) 0.0538(8) Uani 1 1 d . . . C15 C 0.0926(3) 0.6278(4) 0.0614(4) 0.0634(10) Uani 1 1 d . . . C13 C 0.2545(3) 0.4595(3) -0.0316(3) 0.0519(8) Uani 1 1 d . . . H13 H 0.1827 0.4448 -0.0373 0.062 Uiso 1 1 calc R A . C19 C 0.4910(3) -0.0191(3) 0.7771(3) 0.0449(7) Uani 1 1 d . . . H19 H 0.4872 -0.0196 0.8565 0.054 Uiso 1 1 calc R . . C22 C 0.7250(3) -0.0461(3) 0.7382(3) 0.0510(8) Uani 1 1 d . . . F3 F 0.7934(2) -0.1728(2) 0.7803(3) 0.0853(8) Uani 1 1 d . . . F2 F 0.6965(2) -0.0030(3) 0.8291(2) 0.0966(9) Uani 1 1 d . . . F9 F 0.0078(2) 0.6306(4) 0.0087(3) 0.1143(11) Uani 1 1 d . . . F8 F 0.0729(2) 0.7463(3) 0.0447(3) 0.1040(10) Uani 1 1 d . . . C20 C 0.3814(3) -0.0107(3) 0.7465(3) 0.0391(6) Uani 1 1 d . . . C21 C 0.2591(4) -0.0023(5) 0.8423(3) 0.0631(10) Uani 1 1 d . . . O6 O 0.36791(18) -0.00722(18) 0.64632(17) 0.0375(4) Uani 1 1 d . . . F4 F 0.1792(3) 0.1195(5) 0.8102(4) 0.1488(16) Uani 1 1 d . . . F6 F 0.2750(3) -0.0296(5) 0.9518(2) 0.1399(17) Uani 1 1 d . . . F7 F 0.0655(3) 0.5678(4) 0.1806(3) 0.1241(12) Uani 1 1 d . . . F5 F 0.1945(4) -0.0647(5) 0.8440(3) 0.162(2) Uani 1 1 d . . . F10A F 0.3917(17) 0.1814(10) -0.0531(7) 0.103(5) Uani 0.563(19) 1 d PU A 1 F11A F 0.5080(10) 0.2688(13) -0.2061(13) 0.101(4) Uani 0.563(19) 1 d PU A 1 F12A F 0.3103(14) 0.3391(8) -0.2035(12) 0.109(4) Uani 0.563(19) 1 d PU A 1 F10B F 0.4685(15) 0.1731(12) -0.0718(15) 0.096(5) Uani 0.437(19) 1 d PU A 2 F11B F 0.434(3) 0.3261(15) -0.2376(8) 0.116(7) Uani 0.437(19) 1 d PU A 2 F12B F 0.2807(7) 0.2736(16) -0.112(2) 0.107(6) Uani 0.437(19) 1 d PU A 2 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 0.0326(3) 0.0346(3) 0.0304(3) -0.01300(19) -0.00591(18) -0.0113(2) Cu2 0.0304(3) 0.0498(3) 0.0412(3) -0.0251(2) -0.0024(2) -0.0153(2) S1 0.0348(4) 0.0310(3) 0.0389(4) -0.0156(3) -0.0050(3) -0.0100(3) O5 0.0350(10) 0.0414(10) 0.0347(10) -0.0164(8) -0.0072(8) -0.0105(8) O4 0.0415(11) 0.0529(12) 0.0416(11) -0.0247(9) -0.0030(8) -0.0191(9) C18 0.0374(15) 0.0328(13) 0.0421(15) -0.0142(11) -0.0124(12) -0.0078(11) F1 0.0658(14) 0.1076(17) 0.0683(14) -0.0151(12) -0.0215(11) -0.0521(13) O1 0.0450(12) 0.0518(12) 0.0464(12) -0.0291(10) -0.0059(9) -0.0105(10) O2 0.0502(12) 0.0303(10) 0.0580(13) -0.0141(9) -0.0037(10) -0.0134(9) N1 0.0345(13) 0.0363(12) 0.0508(14) -0.0169(11) -0.0128(10) -0.0075(10) C2 0.0389(16) 0.0402(15) 0.0517(18) -0.0139(13) -0.0166(13) -0.0072(13) C5 0.0333(14) 0.0345(13) 0.0379(14) -0.0187(12) -0.0053(11) -0.0099(11) C10 0.0466(18) 0.0454(17) 0.0487(18) -0.0173(14) 0.0025(14) -0.0172(14) C6 0.0474(17) 0.0384(15) 0.0360(15) -0.0158(12) -0.0038(12) -0.0094(13) C8 0.0375(16) 0.0577(19) 0.062(2) -0.0355(17) -0.0087(14) -0.0048(14) C9 0.0417(18) 0.071(2) 0.055(2) -0.0322(18) 0.0086(15) -0.0147(16) C7 0.056(2) 0.0383(15) 0.0505(18) -0.0205(14) -0.0149(15) -0.0023(14) C1 0.052(2) 0.069(2) 0.060(2) -0.0331(18) -0.0164(16) -0.0148(17) C3 0.0396(19) 0.066(2) 0.072(2) -0.0145(19) -0.0200(17) -0.0175(17) C11 0.055(2) 0.086(3) 0.088(3) -0.059(2) -0.013(2) 0.012(2) C4 0.040(2) 0.124(4) 0.093(3) -0.042(3) -0.013(2) -0.007(2) O3 0.0343(10) 0.0575(12) 0.0465(12) -0.0271(10) -0.0011(8) -0.0180(9) C14 0.0366(16) 0.0639(19) 0.0361(15) -0.0163(14) -0.0001(12) -0.0240(14) C12 0.0518(18) 0.0530(17) 0.0362(15) -0.0159(13) -0.0079(13) -0.0277(15) C16 0.068(2) 0.058(2) 0.052(2) -0.0238(17) -0.0118(17) -0.0314(18) C15 0.0368(18) 0.091(3) 0.066(2) -0.036(2) 0.0078(16) -0.0287(19) C13 0.0423(17) 0.072(2) 0.058(2) -0.0297(17) -0.0020(14) -0.0317(16) C19 0.0430(16) 0.0598(18) 0.0386(16) -0.0256(14) -0.0078(12) -0.0140(14) C22 0.0422(17) 0.065(2) 0.0489(18) -0.0227(16) -0.0139(14) -0.0133(16) F3 0.0570(14) 0.0742(15) 0.1060(19) -0.0076(13) -0.0433(13) -0.0096(12) F2 0.0635(14) 0.175(3) 0.0962(18) -0.094(2) -0.0147(13) -0.0315(16) F9 0.0364(12) 0.189(3) 0.157(3) -0.114(3) -0.0087(14) -0.0241(16) F8 0.0451(13) 0.0955(19) 0.169(3) -0.0755(19) 0.0144(15) -0.0150(13) C20 0.0396(15) 0.0430(15) 0.0368(15) -0.0185(12) -0.0018(12) -0.0146(13) C21 0.047(2) 0.113(3) 0.052(2) -0.050(2) 0.0076(16) -0.037(2) O6 0.0383(10) 0.0426(10) 0.0361(10) -0.0167(8) -0.0045(8) -0.0158(9) F4 0.0691(19) 0.189(4) 0.142(3) -0.093(3) 0.0279(19) 0.001(2) F6 0.086(2) 0.310(5) 0.0542(15) -0.089(2) 0.0242(13) -0.094(3) F7 0.0700(18) 0.169(3) 0.0776(18) -0.0363(19) 0.0337(14) -0.0318(18) F5 0.165(3) 0.321(6) 0.117(2) -0.140(3) 0.090(2) -0.201(4) F10A 0.207(14) 0.078(6) 0.053(3) -0.013(3) -0.015(6) -0.090(8) F11A 0.111(6) 0.140(9) 0.110(8) -0.098(7) 0.030(4) -0.071(5) F12A 0.152(9) 0.098(5) 0.122(8) -0.052(6) -0.085(7) -0.024(5) F10B 0.129(9) 0.060(5) 0.121(10) -0.051(6) -0.075(8) 0.008(6) F11B 0.25(2) 0.112(10) 0.033(4) -0.033(5) 0.014(8) -0.124(13) F12B 0.066(4) 0.133(11) 0.194(16) -0.120(12) 0.002(6) -0.049(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O5 1.9325(18) 2_656 ? Cu1 O5 1.9325(18) . ? Cu1 O2 2.3849(19) . ? Cu1 O2 2.3849(19) 2_656 ? Cu1 O6 1.9385(18) 2_656 ? Cu1 O6 1.9386(18) . ? Cu2 O4 1.9267(19) 2_665 ? Cu2 O4 1.9267(19) . ? Cu2 O1 2.581(2) . ? Cu2 O3 1.933(2) . ? Cu2 O3 1.933(2) 2_665 ? S1 O1 1.430(2) . ? S1 O2 1.442(2) . ? S1 N1 1.656(2) . ? S1 C5 1.746(3) . ? O5 C18 1.259(3) . ? O4 C12 1.252(3) . ? C18 C19 1.381(4) . ? C18 C22 1.523(4) . ? F1 C22 1.315(4) . ? N1 C2 1.515(4) . ? N1 C1 1.478(4) . ? C2 C1 1.461(5) . ? C2 C3 1.469(5) . ? C5 C10 1.379(4) . ? C5 C6 1.391(4) . ? C10 C9 1.374(4) . ? C6 C7 1.377(4) . ? C8 C9 1.378(5) . ? C8 C7 1.384(5) . ? C8 C11 1.515(5) . ? C3 C4 1.288(6) . ? O3 C14 1.246(3) . ? C14 C15 1.544(5) . ? C14 C13 1.384(5) . ? C12 C16 1.535(4) . ? C12 C13 1.376(4) . ? C16 F10A 1.244(8) . ? C16 F11A 1.351(9) . ? C16 F12A 1.307(7) . ? C16 F10B 1.309(11) . ? C16 F11B 1.193(10) . ? C16 F12B 1.354(7) . ? C15 F9 1.315(4) . ? C15 F8 1.279(5) . ? C15 F7 1.305(5) . ? C19 C20 1.385(4) . ? C22 F3 1.325(4) . ? C22 F2 1.313(4) . ? C20 C21 1.518(4) . ? C20 O6 1.257(3) . ? C21 F4 1.313(6) . ? C21 F6 1.277(4) . ? C21 F5 1.261(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O5 Cu1 O5 180.0 . 2_656 ? O5 Cu1 O2 90.17(8) . . ? O5 Cu1 O2 90.17(8) 2_656 2_656 ? O5 Cu1 O2 89.83(8) 2_656 . ? O5 Cu1 O2 89.83(8) . 2_656 ? O5 Cu1 O6 86.84(8) . 2_656 ? O5 Cu1 O6 93.16(8) 2_656 2_656 ? O5 Cu1 O6 93.16(8) . . ? O5 Cu1 O6 86.84(8) 2_656 . ? O2 Cu1 O2 180.0 . 2_656 ? O6 Cu1 O2 93.39(7) . 2_656 ? O6 Cu1 O2 86.61(7) 2_656 2_656 ? O6 Cu1 O2 93.39(7) 2_656 . ? O6 Cu1 O2 86.61(7) . . ? O6 Cu1 O6 180.0 2_656 . ? O4 Cu2 O4 179.999(1) . 2_665 ? O4 Cu2 O1 93.92(7) . . ? O4 Cu2 O1 86.08(7) 2_665 . ? O4 Cu2 O3 87.42(8) 2_665 . ? O4 Cu2 O3 87.42(8) . 2_665 ? O4 Cu2 O3 92.58(8) 2_665 2_665 ? O4 Cu2 O3 92.58(8) . . ? O3 Cu2 O1 81.11(8) . . ? O3 Cu2 O1 98.89(8) 2_665 . ? O3 Cu2 O3 180.000(1) 2_665 . ? O1 S1 O2 117.26(13) . . ? O1 S1 N1 106.13(13) . . ? O1 S1 C5 111.47(13) . . ? O2 S1 N1 111.59(13) . . ? O2 S1 C5 107.14(13) . . ? N1 S1 C5 102.27(12) . . ? C18 O5 Cu1 124.12(18) . . ? C12 O4 Cu2 124.61(19) . . ? O5 C18 C19 128.5(3) . . ? O5 C18 C22 112.9(2) . . ? C19 C18 C22 118.5(3) . . ? S1 O1 Cu2 144.60(13) . . ? S1 O2 Cu1 142.80(13) . . ? C2 N1 S1 114.20(19) . . ? C1 N1 S1 116.3(2) . . ? C1 N1 C2 58.4(2) . . ? C1 C2 N1 59.5(2) . . ? C1 C2 C3 123.3(3) . . ? C3 C2 N1 114.9(3) . . ? C10 C5 S1 119.6(2) . . ? C10 C5 C6 120.5(3) . . ? C6 C5 S1 119.9(2) . . ? C9 C10 C5 119.4(3) . . ? C7 C6 C5 118.4(3) . . ? C9 C8 C7 117.7(3) . . ? C9 C8 C11 121.3(3) . . ? C7 C8 C11 120.9(3) . . ? C10 C9 C8 121.8(3) . . ? C6 C7 C8 122.2(3) . . ? C2 C1 N1 62.1(2) . . ? C4 C3 C2 122.3(4) . . ? C14 O3 Cu2 124.5(2) . . ? O3 C14 C15 113.3(3) . . ? O3 C14 C13 128.4(3) . . ? C13 C14 C15 118.3(3) . . ? O4 C12 C16 113.7(3) . . ? O4 C12 C13 128.6(3) . . ? C13 C12 C16 117.8(3) . . ? F10A C16 C12 113.8(4) . . ? F10A C16 F11A 105.8(7) . . ? F10A C16 F12A 109.5(6) . . ? F10A C16 F10B 37.2(5) . . ? F10A C16 F12B 66.7(6) . . ? F11A C16 C12 111.5(5) . . ? F11A C16 F12B 135.2(5) . . ? F12A C16 C12 113.3(4) . . ? F12A C16 F11A 102.0(6) . . ? F12A C16 F10B 134.5(6) . . ? F12A C16 F12B 48.6(5) . . ? F10B C16 C12 110.1(5) . . ? F10B C16 F11A 73.4(7) . . ? F10B C16 F12B 102.6(7) . . ? F11B C16 C12 113.1(5) . . ? F11B C16 F10A 130.7(7) . . ? F11B C16 F11A 41.3(8) . . ? F11B C16 F12A 63.3(8) . . ? F11B C16 F10B 110.6(10) . . ? F11B C16 F12B 108.4(8) . . ? F12B C16 C12 111.5(4) . . ? F9 C15 C14 112.4(3) . . ? F8 C15 C14 113.2(3) . . ? F8 C15 F9 107.4(4) . . ? F8 C15 F7 107.0(4) . . ? F7 C15 C14 109.2(3) . . ? F7 C15 F9 107.2(3) . . ? C12 C13 C14 120.8(3) . . ? C18 C19 C20 121.5(3) . . ? F1 C22 C18 112.8(3) . . ? F1 C22 F3 106.2(3) . . ? F3 C22 C18 109.8(3) . . ? F2 C22 C18 113.1(3) . . ? F2 C22 F1 107.8(3) . . ? F2 C22 F3 106.7(3) . . ? C19 C20 C21 118.1(3) . . ? O6 C20 C19 128.2(3) . . ? O6 C20 C21 113.7(3) . . ? F4 C21 C20 108.7(3) . . ? F6 C21 C20 115.2(3) . . ? F6 C21 F4 104.7(4) . . ? F5 C21 C20 113.5(3) . . ? F5 C21 F4 102.8(4) . . ? F5 C21 F6 111.0(4) . . ? C20 O6 Cu1 124.15(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 Cu1 O5 C18 C19 1.2(4) . . . . ? Cu1 O5 C18 C22 179.59(18) . . . . ? Cu2 O4 C12 C16 175.81(19) . . . . ? Cu2 O4 C12 C13 -4.1(4) . . . . ? Cu2 O3 C14 C15 170.2(2) . . . . ? Cu2 O3 C14 C13 -8.2(5) . . . . ? S1 N1 C2 C1 -107.1(3) . . . . ? S1 N1 C2 C3 137.5(3) . . . . ? S1 N1 C1 C2 103.5(2) . . . . ? S1 C5 C10 C9 -179.9(3) . . . . ? S1 C5 C6 C7 179.8(2) . . . . ? O5 Cu1 O5 C18 100(18) 2_656 . . . ? O5 Cu1 O2 S1 -81.1(2) 2_656 . . . ? O5 Cu1 O2 S1 98.9(2) . . . . ? O5 Cu1 O6 C20 6.5(2) . . . . ? O5 Cu1 O6 C20 -173.5(2) 2_656 . . . ? O5 C18 C19 C20 2.8(5) . . . . ? O5 C18 C22 F1 33.3(4) . . . . ? O5 C18 C22 F3 -84.9(3) . . . . ? O5 C18 C22 F2 156.1(3) . . . . ? O4 Cu2 O4 C12 49(17) 2_665 . . . ? O4 Cu2 O1 S1 -179.6(2) . . . . ? O4 Cu2 O1 S1 0.4(2) 2_665 . . . ? O4 Cu2 O3 C14 -173.0(2) 2_665 . . . ? O4 Cu2 O3 C14 7.0(2) . . . . ? O4 C12 C16 F10A 93.4(9) . . . . ? O4 C12 C16 F11A -26.2(8) . . . . ? O4 C12 C16 F12A -140.7(9) . . . . ? O4 C12 C16 F10B 53.3(10) . . . . ? O4 C12 C16 F11B -71.0(15) . . . . ? O4 C12 C16 F12B 166.5(11) . . . . ? O4 C12 C13 C14 5.1(5) . . . . ? C18 C19 C20 C21 -179.8(3) . . . . ? C18 C19 C20 O6 -0.8(5) . . . . ? O1 Cu2 O4 C12 80.0(2) . . . . ? O1 Cu2 O3 C14 -86.6(2) . . . . ? O1 S1 O2 Cu1 33.1(3) . . . . ? O1 S1 N1 C2 -91.4(2) . . . . ? O1 S1 N1 C1 -156.6(2) . . . . ? O1 S1 C5 C10 138.0(2) . . . . ? O1 S1 C5 C6 -41.7(3) . . . . ? O2 Cu1 O5 C18 81.8(2) . . . . ? O2 Cu1 O5 C18 -98.2(2) 2_656 . . . ? O2 Cu1 O2 S1 86(39) 2_656 . . . ? O2 Cu1 O6 C20 96.5(2) 2_656 . . . ? O2 Cu1 O6 C20 -83.5(2) . . . . ? O2 S1 O1 Cu2 -168.74(18) . . . . ? O2 S1 N1 C2 37.5(2) . . . . ? O2 S1 N1 C1 -27.8(2) . . . . ? O2 S1 C5 C10 8.5(3) . . . . ? O2 S1 C5 C6 -171.3(2) . . . . ? N1 S1 O1 Cu2 -43.3(2) . . . . ? N1 S1 O2 Cu1 -89.6(2) . . . . ? N1 S1 C5 C10 -109.0(3) . . . . ? N1 S1 C5 C6 71.3(3) . . . . ? N1 C2 C3 C4 -140.9(4) . . . . ? C5 S1 O1 Cu2 67.3(2) . . . . ? C5 S1 O2 Cu1 159.3(2) . . . . ? C5 S1 N1 C2 151.7(2) . . . . ? C5 S1 N1 C1 86.5(2) . . . . ? C5 C10 C9 C8 0.3(5) . . . . ? C5 C6 C7 C8 -0.1(5) . . . . ? C10 C5 C6 C7 0.0(5) . . . . ? C6 C5 C10 C9 -0.1(5) . . . . ? C9 C8 C7 C6 0.3(5) . . . . ? C7 C8 C9 C10 -0.4(5) . . . . ? C1 N1 C2 C3 -115.4(4) . . . . ? C1 C2 C3 C4 150.5(4) . . . . ? C3 C2 C1 N1 101.4(3) . . . . ? C11 C8 C9 C10 178.3(3) . . . . ? C11 C8 C7 C6 -178.4(3) . . . . ? O3 Cu2 O4 C12 -1.3(2) . . . . ? O3 Cu2 O4 C12 178.7(2) 2_665 . . . ? O3 Cu2 O1 S1 92.4(2) 2_665 . . . ? O3 Cu2 O1 S1 -87.6(2) . . . . ? O3 Cu2 O3 C14 -133(89) 2_665 . . . ? O3 C14 C15 F9 155.6(3) . . . . ? O3 C14 C15 F8 33.6(5) . . . . ? O3 C14 C15 F7 -85.6(4) . . . . ? O3 C14 C13 C12 1.8(5) . . . . ? C16 C12 C13 C14 -174.8(3) . . . . ? C15 C14 C13 C12 -176.5(3) . . . . ? C13 C14 C15 F9 -25.9(5) . . . . ? C13 C14 C15 F8 -147.8(4) . . . . ? C13 C14 C15 F7 93.0(4) . . . . ? C13 C12 C16 F10A -86.7(9) . . . . ? C13 C12 C16 F11A 153.7(8) . . . . ? C13 C12 C16 F12A 39.3(10) . . . . ? C13 C12 C16 F10B -126.8(10) . . . . ? C13 C12 C16 F11B 108.9(14) . . . . ? C13 C12 C16 F12B -13.6(11) . . . . ? C19 C18 C22 F1 -148.1(3) . . . . ? C19 C18 C22 F3 93.6(3) . . . . ? C19 C18 C22 F2 -25.4(4) . . . . ? C19 C20 C21 F4 103.8(4) . . . . ? C19 C20 C21 F6 -13.2(6) . . . . ? C19 C20 C21 F5 -142.6(4) . . . . ? C19 C20 O6 Cu1 -4.8(4) . . . . ? C22 C18 C19 C20 -175.4(3) . . . . ? C21 C20 O6 Cu1 174.2(2) . . . . ? O6 Cu1 O5 C18 -4.8(2) . . . . ? O6 Cu1 O5 C18 175.2(2) 2_656 . . . ? O6 Cu1 O2 S1 12.0(2) 2_656 . . . ? O6 Cu1 O2 S1 -168.0(2) . . . . ? O6 Cu1 O6 C20 110(36) 2_656 . . . ? O6 C20 C21 F4 -75.4(4) . . . . ? O6 C20 C21 F6 167.6(4) . . . . ? O6 C20 C21 F5 38.3(5) . . . . ? _vrf ; PROBLEM: Hirshfeld Test Diff for F4 -- C21 .. 8.5 su Check Low Ueq as Compared to Neighbors for C21 Atom F5 has ADP max/min Ratio ..... 3.3 prola Atom F6 has ADP max/min Ratio ..... 3.2 prola Atom F11B has ADP max/min Ratio ..... 3.4 prola Check Low Ueq as Compared to Neighbors for C15 Check Low Ueq as Compared to Neighbors for C16 Check Low Ueq as Compared to Neighbors for C22 RESPONSE: The fluorine atoms of the CF3 substituents are disordered and have large displacement ellispoids compared to the carbon atoms they are bonded to. This gives rise to all of these checkcif errors. ; data_I _database_code_depnum_ccdc_archive 'CCDC 886195' #TrackingRef '11836_web_deposit_cif_file_4_JonT.Njardarson_1339529666.5_Aziridine15.cif' _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H20 Cl N O2 S' _chemical_formula_iupac ? _chemical_formula_weight 409.91 _chemical_absolute_configuration ad _chemical_melting_point ? _space_group_crystal_system monoclinic _space_group_name_H-M_alt 'P 1 21 1' _space_group_name_Hall 'P 2yb' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.3431(4) _cell_length_b 9.0814(4) _cell_length_c 10.9394(4) _cell_angle_alpha 90 _cell_angle_beta 102.940(2) _cell_angle_gamma 90 _cell_volume 1001.44(7) _cell_formula_units_Z 2 _cell_measurement_reflns_used 9950 _cell_measurement_theta_min 2.4501 _cell_measurement_theta_max 29.8471 _cell_measurement_temperature 100.(2) _exptl_crystal_description 'rod that was cut down to a box' _exptl_crystal_colour 'clear colourless' _exptl_crystal_size_max 0.400 _exptl_crystal_size_mid 0.300 _exptl_crystal_size_min 0.200 _exptl_crystal_density_diffrn 1.359 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 428 _exptl_absorpt_coefficient_mu 0.314 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_absorpt_correction_T_min 0.89 _exptl_absorpt_correction_T_max 0.94 _exptl_special_details ; ; _diffrn_ambient_temperature 100.(2) _diffrn_source ? _diffrn_source_type ? _diffrn_radiation_type ? _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator ? _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 24912 _diffrn_reflns_av_R_equivalents 0.0242 _diffrn_reflns_av_sigmaI/netI 0.0241 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 29.94 _diffrn_reflns_theta_full 29.94 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _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. ; _reflns_number_total 5721 _reflns_number_gt 5561 _reflns_threshold_expression >2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0279 _refine_ls_R_factor_gt 0.0268 _refine_ls_wR_factor_gt 0.0625 _refine_ls_wR_factor_ref 0.0631 _refine_ls_goodness_of_fit_ref 0.975 _refine_ls_restrained_S_all 0.975 _refine_ls_number_reflns 5721 _refine_ls_number_parameters 254 _refine_ls_number_restraints 1 _refine_ls_hydrogen_treatment noref _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0273P)^2^+0.3328P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.340 _refine_diff_density_min -0.253 _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 0.00(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection 'Bruker Instrument Service v2011.2.0.0' _computing_cell_refinement 'SAINT V7.68A (Bruker AXS, 2009)' _computing_data_reduction 'SAINT V7.68A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group S S1 0.52734(3) 0.51568(3) 0.29450(2) 0.01539(6) Uani d . 1 . . Cl Cl1 1.06847(3) 0.34121(4) 1.08968(3) 0.02894(8) Uani d . 1 . . O O1 0.61442(10) 0.64120(11) 0.31262(9) 0.0236(2) Uani d . 1 . . O O2 0.58640(9) 0.37286(11) 0.32726(8) 0.01953(19) Uani d . 1 . . N N1 0.40804(10) 0.55462(12) 0.36803(9) 0.01593(19) Uani d . 1 . . C C17 0.43614(10) 0.50763(16) 0.13783(10) 0.0154(2) Uani d . 1 . . C C22 0.34485(13) 0.61700(15) 0.08925(13) 0.0207(2) Uani d . 1 . . H H22 0.3262 0.6942 0.1413 0.025 Uiso calc R 1 . . C C11 0.19940(12) 0.43470(15) 0.40560(11) 0.0174(2) Uani d . 1 . . C C18 0.46432(13) 0.39466(15) 0.06269(12) 0.0206(2) Uani d . 1 . . H H18 0.5263 0.3201 0.0969 0.025 Uiso calc R 1 . . C C5 0.72157(11) 0.51111(16) 0.79554(10) 0.0174(2) Uani d . 1 . . C C8 0.93701(12) 0.41018(15) 0.97699(12) 0.0208(2) Uani d . 1 . . C C1 0.34675(11) 0.43457(14) 0.42661(11) 0.0157(2) Uani d . 1 . . H H1 0.3881 0.3354 0.4242 0.019 Uiso calc R 1 . . C C10 0.82769(13) 0.44013(16) 0.76105(12) 0.0206(2) Uani d . 1 . . H H10 0.8266 0.4269 0.6747 0.025 Uiso calc R 1 . . C C3 0.56038(11) 0.50144(15) 0.58919(10) 0.0181(2) Uani d . 1 . . H H3 0.6138 0.4309 0.5594 0.022 Uiso calc R 1 . . C C6 0.72831(12) 0.53470(15) 0.92311(11) 0.0202(2) Uani d . 1 . . H H6 0.6583 0.5859 0.948 0.024 Uiso calc R 1 . . C C21 0.28142(13) 0.61123(16) -0.03686(13) 0.0222(3) Uani d . 1 . . H H21 0.2178 0.6845 -0.0706 0.027 Uiso calc R 1 . . C C9 0.93502(13) 0.38852(16) 0.85120(12) 0.0230(3) Uani d . 1 . . H H9 1.0062 0.339 0.8268 0.028 Uiso calc R 1 . . C C4 0.60213(12) 0.55795(14) 0.70365(11) 0.0183(2) Uani d . 1 . . H H4 0.5506 0.6347 0.7278 0.022 Uiso calc R 1 . . C C7 0.83546(13) 0.48461(15) 1.01436(12) 0.0222(3) Uani d . 1 . . H H7 0.8389 0.5012 1.1008 0.027 Uiso calc R 1 . . C C20 0.30951(12) 0.49973(16) -0.11476(11) 0.0196(2) Uani d . 1 . . C C14 -0.07548(14) 0.4280(2) 0.37413(13) 0.0337(4) Uani d . 1 . . H H14 -0.1691 0.4258 0.3637 0.04 Uiso calc R 1 . . C C2 0.43252(11) 0.54657(14) 0.50786(11) 0.0166(2) Uani d . 1 . . H H2 0.3824 0.6209 0.5463 0.02 Uiso calc R 1 . . C C19 0.40042(14) 0.39187(16) -0.06383(12) 0.0230(3) Uani d . 1 . . H H19 0.4195 0.3149 -0.1159 0.028 Uiso calc R 1 . . C C16 0.12511(13) 0.56013(17) 0.36745(13) 0.0237(3) Uani d . 1 . . H H16 0.1679 0.6484 0.3517 0.028 Uiso calc R 1 . . C C12 0.13635(13) 0.30531(17) 0.42754(12) 0.0238(3) Uani d . 1 . . H H12 0.1869 0.219 0.4535 0.029 Uiso calc R 1 . . C C23 0.24286(14) 0.49886(19) -0.25266(11) 0.0275(3) Uani d . 1 . . H H23A 0.2672 0.4089 -0.2915 0.041 Uiso calc R 1 . . H H23B 0.2717 0.585 -0.2935 0.041 Uiso calc R 1 . . H H23C 0.1464 0.5022 -0.2623 0.041 Uiso calc R 1 . . C C13 -0.00142(14) 0.3026(2) 0.41132(13) 0.0333(4) Uani d . 1 . . H H13 -0.0445 0.2141 0.4259 0.04 Uiso calc R 1 . . C C15 -0.01258(13) 0.55698(19) 0.35210(13) 0.0303(3) Uani d . 1 . . H H15 -0.0633 0.6433 0.3265 0.036 Uiso calc R 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 S1 0.01256(11) 0.01852(13) 0.01501(11) -0.00162(11) 0.00291(9) 0.00138(11) Cl1 0.02600(15) 0.03296(19) 0.02249(14) 0.00565(14) -0.00596(11) 0.00287(13) O1 0.0206(4) 0.0260(5) 0.0232(5) -0.0089(4) 0.0027(4) 0.0016(4) O2 0.0158(4) 0.0223(5) 0.0204(4) 0.0032(3) 0.0036(3) 0.0033(3) N1 0.0151(4) 0.0188(5) 0.0136(4) -0.0011(4) 0.0026(3) -0.0002(4) C17 0.0148(4) 0.0182(5) 0.0137(4) -0.0022(5) 0.0041(4) 0.0019(5) C22 0.0239(6) 0.0186(6) 0.0193(6) 0.0038(5) 0.0044(5) -0.0014(4) C11 0.0142(5) 0.0260(6) 0.0116(5) -0.0018(5) 0.0022(4) -0.0022(4) C18 0.0220(6) 0.0214(6) 0.0192(6) 0.0049(5) 0.0064(5) 0.0014(5) C5 0.0184(5) 0.0159(5) 0.0162(5) -0.0042(5) 0.0002(4) 0.0011(5) C8 0.0195(6) 0.0198(6) 0.0194(6) -0.0019(5) -0.0034(4) 0.0035(5) C1 0.0143(5) 0.0183(6) 0.0143(5) -0.0006(4) 0.0029(4) 0.0010(4) C10 0.0203(6) 0.0246(7) 0.0156(5) -0.0017(5) 0.0013(4) 0.0011(5) C3 0.0164(5) 0.0192(6) 0.0179(5) -0.0019(5) 0.0020(4) 0.0007(5) C6 0.0227(5) 0.0195(7) 0.0172(5) 0.0003(5) 0.0019(4) -0.0015(5) C21 0.0242(6) 0.0219(6) 0.0197(6) 0.0050(5) 0.0029(5) 0.0019(5) C9 0.0189(6) 0.0271(7) 0.0222(6) 0.0017(5) 0.0027(5) 0.0027(5) C4 0.0177(5) 0.0180(6) 0.0180(5) -0.0006(4) 0.0016(4) 0.0021(4) C7 0.0271(6) 0.0220(7) 0.0155(5) -0.0001(5) 0.0004(4) -0.0004(5) C20 0.0197(5) 0.0239(6) 0.0159(5) -0.0030(5) 0.0050(4) -0.0005(5) C14 0.0141(6) 0.0653(12) 0.0212(6) -0.0015(6) 0.0029(5) -0.0004(7) C2 0.0174(5) 0.0182(6) 0.0138(5) -0.0007(4) 0.0025(4) -0.0008(4) C19 0.0282(6) 0.0242(7) 0.0181(6) 0.0039(5) 0.0080(5) -0.0030(5) C16 0.0196(6) 0.0275(7) 0.0230(6) 0.0026(5) 0.0027(5) -0.0039(5) C12 0.0192(6) 0.0306(8) 0.0196(6) -0.0057(5) 0.0004(4) 0.0049(5) C23 0.0302(6) 0.0367(8) 0.0148(5) 0.0002(6) 0.0039(4) -0.0001(6) C13 0.0197(6) 0.0543(11) 0.0239(7) -0.0142(6) 0.0006(5) 0.0089(6) C15 0.0193(6) 0.0457(10) 0.0239(6) 0.0096(6) 0.0006(5) -0.0071(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_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag S1 O1 . 1.4387(10) ? S1 O2 . 1.4443(10) ? S1 N1 . 1.6550(10) ? S1 C17 . 1.7631(11) ? Cl1 C8 . 1.7350(13) ? N1 C1 . 1.4775(16) ? N1 C2 . 1.4952(15) ? C17 C18 . 1.3857(18) ? C17 C22 . 1.3913(18) ? C22 C21 . 1.3896(18) ? C11 C16 . 1.3851(19) ? C11 C12 . 1.3906(19) ? C11 C1 . 1.4895(16) ? C18 C19 . 1.3941(18) ? C5 C10 . 1.3958(18) ? C5 C6 . 1.3981(16) ? C5 C4 . 1.4702(16) ? C8 C9 . 1.3857(19) ? C8 C7 . 1.3854(19) ? C1 C2 . 1.5028(17) ? C10 C9 . 1.3908(17) ? C3 C4 . 1.3325(17) ? C3 C2 . 1.4770(16) ? C6 C7 . 1.3914(17) ? C21 C20 . 1.3953(19) ? C20 C19 . 1.3854(19) ? C20 C23 . 1.5116(16) ? C14 C13 . 1.382(3) ? C14 C15 . 1.387(3) ? C16 C15 . 1.3965(18) ? C12 C13 . 1.3961(18) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O1 S1 O2 . . 117.41(6) ? O1 S1 N1 . . 106.00(6) ? O2 S1 N1 . . 113.03(5) ? O1 S1 C17 . . 110.42(6) ? O2 S1 C17 . . 107.96(6) ? N1 S1 C17 . . 100.75(5) ? C1 N1 C2 . . 60.73(8) ? C1 N1 S1 . . 119.48(8) ? C2 N1 S1 . . 120.86(8) ? C18 C17 C22 . . 121.12(11) ? C18 C17 S1 . . 118.00(10) ? C22 C17 S1 . . 120.75(10) ? C17 C22 C21 . . 118.78(12) ? C16 C11 C12 . . 119.80(11) ? C16 C11 C1 . . 121.77(12) ? C12 C11 C1 . . 118.42(12) ? C17 C18 C19 . . 119.11(12) ? C10 C5 C6 . . 118.31(11) ? C10 C5 C4 . . 122.69(11) ? C6 C5 C4 . . 118.99(11) ? C9 C8 C7 . . 121.24(12) ? C9 C8 Cl1 . . 119.29(11) ? C7 C8 Cl1 . . 119.46(10) ? N1 C1 C11 . . 117.13(10) ? N1 C1 C2 . . 60.22(7) ? C11 C1 C2 . . 122.61(11) ? C9 C10 C5 . . 121.00(12) ? C4 C3 C2 . . 121.15(12) ? C7 C6 C5 . . 121.31(12) ? C20 C21 C22 . . 121.14(12) ? C8 C9 C10 . . 119.23(13) ? C3 C4 C5 . . 125.24(12) ? C8 C7 C6 . . 118.85(12) ? C19 C20 C21 . . 118.87(11) ? C19 C20 C23 . . 120.96(12) ? C21 C20 C23 . . 120.16(12) ? C13 C14 C15 . . 119.76(13) ? C3 C2 N1 . . 123.61(10) ? C3 C2 C1 . . 119.92(11) ? N1 C2 C1 . . 59.05(7) ? C20 C19 C18 . . 120.97(12) ? C11 C16 C15 . . 120.10(14) ? C11 C12 C13 . . 119.85(14) ? C14 C13 C12 . . 120.38(15) ? C14 C15 C16 . . 120.11(14) ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag O1 S1 N1 C1 . . . . -147.45(9) ? O2 S1 N1 C1 . . . . -17.49(10) ? C17 S1 N1 C1 . . . . 97.46(9) ? O1 S1 N1 C2 . . . . -75.90(10) ? O2 S1 N1 C2 . . . . 54.06(10) ? C17 S1 N1 C2 . . . . 169.01(9) ? O1 S1 C17 C18 . . . . 110.97(11) ? O2 S1 C17 C18 . . . . -18.61(11) ? N1 S1 C17 C18 . . . . -137.31(10) ? O1 S1 C17 C22 . . . . -64.95(11) ? O2 S1 C17 C22 . . . . 165.47(10) ? N1 S1 C17 C22 . . . . 46.77(11) ? C18 C17 C22 C21 . . . . 0.15(19) ? S1 C17 C22 C21 . . . . 175.93(10) ? C22 C17 C18 C19 . . . . 0.46(19) ? S1 C17 C18 C19 . . . . -175.44(10) ? C2 N1 C1 C11 . . . . 113.85(12) ? S1 N1 C1 C11 . . . . -135.14(10) ? S1 N1 C1 C2 . . . . 111.01(9) ? C16 C11 C1 N1 . . . . -19.17(17) ? C12 C11 C1 N1 . . . . 162.06(11) ? C16 C11 C1 C2 . . . . 51.28(16) ? C12 C11 C1 C2 . . . . -127.49(13) ? C6 C5 C10 C9 . . . . 2.7(2) ? C4 C5 C10 C9 . . . . -175.58(13) ? C10 C5 C6 C7 . . . . -2.2(2) ? C4 C5 C6 C7 . . . . 176.09(12) ? C17 C22 C21 C20 . . . . -1.0(2) ? C7 C8 C9 C10 . . . . -1.3(2) ? Cl1 C8 C9 C10 . . . . 178.14(11) ? C5 C10 C9 C8 . . . . -1.0(2) ? C2 C3 C4 C5 . . . . 174.39(11) ? C10 C5 C4 C3 . . . . 22.6(2) ? C6 C5 C4 C3 . . . . -155.59(13) ? C9 C8 C7 C6 . . . . 1.7(2) ? Cl1 C8 C7 C6 . . . . -177.71(10) ? C5 C6 C7 C8 . . . . 0.1(2) ? C22 C21 C20 C19 . . . . 1.3(2) ? C22 C21 C20 C23 . . . . -177.80(13) ? C4 C3 C2 N1 . . . . 147.50(12) ? C4 C3 C2 C1 . . . . -141.76(13) ? C1 N1 C2 C3 . . . . 107.45(13) ? S1 N1 C2 C3 . . . . -1.36(16) ? S1 N1 C2 C1 . . . . -108.81(10) ? N1 C1 C2 C3 . . . . -113.55(12) ? C11 C1 C2 C3 . . . . 141.52(12) ? C11 C1 C2 N1 . . . . -104.93(12) ? C21 C20 C19 C18 . . . . -0.7(2) ? C23 C20 C19 C18 . . . . 178.42(13) ? C17 C18 C19 C20 . . . . -0.2(2) ? C12 C11 C16 C15 . . . . 0.53(19) ? C1 C11 C16 C15 . . . . -178.22(12) ? C16 C11 C12 C13 . . . . -0.2(2) ? C1 C11 C12 C13 . . . . 178.64(12) ? C15 C14 C13 C12 . . . . 0.4(2) ? C11 C12 C13 C14 . . . . -0.3(2) ? C13 C14 C15 C16 . . . . 0.0(2) ? C11 C16 C15 C14 . . . . -0.5(2) ? data_Ia _database_code_depnum_ccdc_archive 'CCDC 886196' #TrackingRef '11837_web_deposit_cif_file_5_JonT.Njardarson_1339529666.6_pyrroleSI2.cif' _chemical_name_systematic ? _chemical_name_common jn203b _chemical_formula_moiety ? _chemical_formula_sum 'C23 H20 Cl N O2 S' _chemical_formula_iupac ? _chemical_formula_weight 409.91 _chemical_absolute_configuration ad _chemical_melting_point ? _space_group_crystal_system monoclinic _space_group_name_H-M_alt 'P 1 21 1' _space_group_name_Hall 'P 2yb' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.9219(4) _cell_length_b 12.6553(4) _cell_length_c 13.5310(4) _cell_angle_alpha 90 _cell_angle_beta 106.461(2) _cell_angle_gamma 90 _cell_volume 1957.82(11) _cell_formula_units_Z 4 _cell_measurement_reflns_used 7510 _cell_measurement_theta_min 2.2479 _cell_measurement_theta_max 24.2807 _cell_measurement_temperature 100.(2) _exptl_crystal_description plate _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.391 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856 _exptl_absorpt_coefficient_mu 0.321 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_absorpt_correction_T_min 0.88 _exptl_absorpt_correction_T_max 1.00 _exptl_special_details ; ; _diffrn_ambient_temperature 100.(2) _diffrn_source ? _diffrn_source_type ? _diffrn_radiation_type ? _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator ? _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 33148 _diffrn_reflns_av_R_equivalents 0.0501 _diffrn_reflns_av_sigmaI/netI 0.0403 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 24.36 _diffrn_reflns_theta_full 24.36 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _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. ; _reflns_number_total 6414 _reflns_number_gt 5697 _reflns_threshold_expression >2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0426 _refine_ls_R_factor_gt 0.0343 _refine_ls_wR_factor_gt 0.0778 _refine_ls_wR_factor_ref 0.0819 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _refine_ls_number_reflns 6414 _refine_ls_number_parameters 507 _refine_ls_number_restraints 1 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0378P)^2^+0.8444P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.431 _refine_diff_density_min -0.316 _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 0.01(5) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection ? _computing_cell_refinement 'SAINT V7.68A (Bruker AXS, 2009)' _computing_data_reduction 'SAINT V7.68A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group S S2 -0.00031(6) 0.53607(5) 0.96651(5) 0.01687(16) Uani d . 1 . . S S1 0.49008(6) 0.05413(5) 0.02576(5) 0.01746(17) Uani d . 1 . . Cl Cl1 0.33366(7) -0.00705(6) 0.53419(5) 0.02946(19) Uani d . 1 . . Cl Cl2 -0.44033(7) 0.21803(7) 0.55948(6) 0.0389(2) Uani d . 1 . . O O1 0.60832(16) 0.05716(16) 0.02046(14) 0.0216(5) Uani d . 1 . . O O4 -0.11751(16) 0.52302(16) 0.97375(14) 0.0202(5) Uani d . 1 . . O O3 0.03498(17) 0.63518(15) 0.93383(15) 0.0225(5) Uani d . 1 . . O O2 0.44408(17) -0.04068(15) 0.05698(15) 0.0212(5) Uani d . 1 . . N N2 0.0184(2) 0.44673(18) 0.88584(17) 0.0160(5) Uani d . 1 . . N N1 0.4805(2) 0.14558(19) 0.10722(17) 0.0168(5) Uani d . 1 . . C C40 0.0948(2) 0.5065(2) 1.0892(2) 0.0160(6) Uani d . 1 . . C C1 0.3647(2) 0.1609(2) 0.1262(2) 0.0169(6) Uani d . 1 . . H H1 0.3014 0.1304 0.0681 0.02 Uiso calc R 1 . . C C18 0.2868(2) 0.0471(3) -0.1314(2) 0.0204(6) Uani d . 1 . . H H18 0.261 -0.0039 -0.0912 0.024 Uiso calc R 1 . . C C22 0.4371(3) 0.1630(2) -0.1565(2) 0.0219(7) Uani d . 1 . . H H22 0.5143 0.1905 -0.1334 0.026 Uiso calc R 1 . . C C41 0.0552(3) 0.4425(2) 1.1564(2) 0.0192(7) Uani d . 1 . . H H41 -0.0234 0.4181 1.1377 0.023 Uiso calc R 1 . . C C10 0.4499(2) 0.0594(2) 0.2925(2) 0.0186(6) Uani d . 1 . . H H10 0.5191 0.0476 0.2727 0.022 Uiso calc R 1 . . C C11 0.6579(3) 0.2564(2) 0.1886(2) 0.0191(7) Uani d . 1 . . C C19 0.2136(3) 0.0796(2) -0.2259(2) 0.0230(7) Uani d . 1 . . H H19 0.1376 0.0498 -0.2503 0.028 Uiso calc R 1 . . C C39 0.2217(2) 0.4894(2) 0.7184(2) 0.0209(7) Uani d . 1 . . H H39 0.2946 0.4955 0.7697 0.025 Uiso calc R 1 . . C C38 0.2166(3) 0.5021(2) 0.6156(2) 0.0232(7) Uani d . 1 . . H H38 0.2861 0.5164 0.5969 0.028 Uiso calc R 1 . . C C42 0.1318(3) 0.4150(2) 1.2505(2) 0.0225(7) Uani d . 1 . . H H42 0.1053 0.3714 1.2965 0.027 Uiso calc R 1 . . C C34 0.1206(2) 0.4679(2) 0.7473(2) 0.0165(6) Uani d . 1 . . C C44 0.2839(2) 0.5160(2) 1.2109(2) 0.0209(7) Uani d . 1 . . H H44 0.3621 0.5414 1.2298 0.025 Uiso calc R 1 . . C C20 0.2494(3) 0.1551(2) -0.2854(2) 0.0215(7) Uani d . 1 . . C C17 0.3980(2) 0.0902(2) -0.0967(2) 0.0186(7) Uani d . 1 . . C C43 0.2479(3) 0.4507(2) 1.2789(2) 0.0217(7) Uani d . 1 . . C C16 0.7618(3) 0.2442(2) 0.1628(2) 0.0213(7) Uani d . 1 . . H H16 0.7599 0.2329 0.0929 0.026 Uiso calc R 1 . . C C37 0.1102(2) 0.4941(2) 0.5397(2) 0.0230(7) Uani d . 1 . . H H37 0.1066 0.5024 0.4691 0.028 Uiso calc R 1 . . C C24 0.1326(2) 0.4470(2) 0.8601(2) 0.0182(6) Uani d . 1 . . H H24 0.1876 0.4991 0.9043 0.022 Uiso calc R 1 . . C C21 0.3631(3) 0.1948(3) -0.2494(2) 0.0241(7) Uani d . 1 . . H H21 0.3898 0.2448 -0.29 0.029 Uiso calc R 1 . . C C25 0.1753(3) 0.3356(2) 0.8882(2) 0.0206(7) Uani d . 1 . . H H25 0.251 0.3112 0.8894 0.025 Uiso calc R 1 . . C C46 0.3309(3) 0.4160(3) 1.3785(2) 0.0346(9) Uani d . 1 . . H H46A 0.3755 0.3548 1.3664 0.052 Uiso calc R 1 . . H H46B 0.2868 0.3965 1.4269 0.052 Uiso calc R 1 . . H H46C 0.3847 0.4739 1.4076 0.052 Uiso calc R 1 . . C C6 0.2574(2) 0.1324(2) 0.2591(2) 0.0204(7) Uani d . 1 . . H H6 0.1934 0.1696 0.215 0.024 Uiso calc R 1 . . C C29 -0.2331(2) 0.3288(2) 0.8246(2) 0.0202(7) Uani d . 1 . . H H29 -0.2418 0.3666 0.8827 0.024 Uiso calc R 1 . . C C7 0.2496(2) 0.0962(2) 0.3529(2) 0.0208(7) Uani d . 1 . . H H7 0.1813 0.1091 0.3739 0.025 Uiso calc R 1 . . C C28 -0.1218(2) 0.2995(2) 0.8204(2) 0.0170(6) Uani d . 1 . . C C12 0.6622(3) 0.2733(2) 0.2906(2) 0.0234(7) Uani d . 1 . . H H12 0.5916 0.281 0.3093 0.028 Uiso calc R 1 . . C C32 -0.2086(3) 0.2171(3) 0.6556(2) 0.0259(7) Uani d . 1 . . H H32 -0.2008 0.1785 0.5977 0.031 Uiso calc R 1 . . C C2 0.3550(3) 0.2791(2) 0.1262(2) 0.0202(7) Uani d . 1 . . H H2 0.2875 0.3159 0.1315 0.024 Uiso calc R 1 . . C C26 0.0955(2) 0.2764(2) 0.9108(2) 0.0206(7) Uani d . 1 . . H H26 0.1069 0.2039 0.9288 0.025 Uiso calc R 1 . . C C31 -0.3173(3) 0.2491(2) 0.6613(2) 0.0254(7) Uani d . 1 . . C C9 0.4417(2) 0.0210(2) 0.3857(2) 0.0202(7) Uani d . 1 . . H H9 0.5041 -0.0188 0.4289 0.024 Uiso calc R 1 . . C C3 0.4503(3) 0.3260(2) 0.1179(2) 0.0210(7) Uani d . 1 . . H H3 0.4602 0.4006 0.1195 0.025 Uiso calc R 1 . . C C30 -0.3308(3) 0.3034(2) 0.7453(2) 0.0222(7) Uani d . 1 . . H H30 -0.4065 0.3232 0.7486 0.027 Uiso calc R 1 . . C C14 0.8723(3) 0.2665(2) 0.3399(2) 0.0256(7) Uani d . 1 . . H H14 0.9453 0.27 0.3915 0.031 Uiso calc R 1 . . C C15 0.8686(3) 0.2484(2) 0.2382(2) 0.0250(7) Uani d . 1 . . H H15 0.9392 0.2389 0.2199 0.03 Uiso calc R 1 . . C C33 -0.1111(3) 0.2422(2) 0.7362(2) 0.0213(6) Uani d . 1 . . H H33 -0.0359 0.2199 0.7337 0.026 Uiso calc R 1 . . C C35 0.0150(2) 0.4611(2) 0.6712(2) 0.0197(6) Uani d . 1 . . H H35 -0.0548 0.4476 0.6898 0.024 Uiso calc R 1 . . C C23 0.1680(3) 0.1958(3) -0.3846(2) 0.0285(8) Uani d . 1 . . H H23A 0.1012 0.1478 -0.4078 0.043 Uiso calc R 1 . . H H23B 0.2098 0.1998 -0.4373 0.043 Uiso calc R 1 . . H H23C 0.1401 0.2664 -0.3733 0.043 Uiso calc R 1 . . C C8 0.3423(2) 0.0407(2) 0.4159(2) 0.0212(6) Uani d . 1 . . C C36 0.0096(3) 0.4737(2) 0.5684(2) 0.0228(7) Uani d . 1 . . H H36 -0.0635 0.4684 0.5171 0.027 Uiso calc R 1 . . C C13 0.7690(3) 0.2793(2) 0.3660(2) 0.0254(7) Uani d . 1 . . H H13 0.7711 0.2922 0.4357 0.03 Uiso calc R 1 . . C C4 0.5416(2) 0.2497(2) 0.1059(2) 0.0177(6) Uani d . 1 . . H H4 0.5548 0.26 0.0368 0.021 Uiso calc R 1 . . C C5 0.3580(2) 0.1152(2) 0.2276(2) 0.0163(6) Uani d . 1 . . C C27 -0.0151(2) 0.3348(2) 0.9053(2) 0.0176(6) Uani d . 1 . . H H27 -0.0322 0.3311 0.9735 0.021 Uiso calc R 1 . . C C45 0.2094(2) 0.5447(2) 1.1172(2) 0.0190(6) Uani d . 1 . . H H45 0.2354 0.5899 1.0721 0.023 Uiso calc R 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 S2 0.0154(3) 0.0163(4) 0.0204(4) 0.0001(3) 0.0074(3) -0.0006(3) S1 0.0163(4) 0.0184(4) 0.0191(4) 0.0018(3) 0.0073(3) -0.0017(3) Cl1 0.0317(4) 0.0351(5) 0.0254(4) -0.0001(4) 0.0143(3) 0.0057(3) Cl2 0.0340(5) 0.0421(5) 0.0321(4) -0.0158(4) -0.0041(4) -0.0007(4) O1 0.0164(10) 0.0272(12) 0.0229(10) 0.0036(9) 0.0080(8) -0.0035(10) O4 0.0160(10) 0.0208(12) 0.0259(11) -0.0009(9) 0.0096(9) -0.0006(9) O3 0.0261(12) 0.0152(11) 0.0284(12) -0.0031(9) 0.0113(10) 0.0016(9) O2 0.0230(11) 0.0172(11) 0.0250(11) 0.0007(9) 0.0095(9) -0.0011(9) N2 0.0159(12) 0.0144(13) 0.0204(13) -0.0017(10) 0.0096(10) -0.0031(10) N1 0.0154(13) 0.0167(13) 0.0193(13) 0.0011(10) 0.0067(10) -0.0001(10) C40 0.0139(14) 0.0146(15) 0.0212(15) -0.0009(12) 0.0077(12) -0.0060(13) C1 0.0169(15) 0.0182(16) 0.0162(14) 0.0022(12) 0.0055(12) -0.0007(12) C18 0.0192(15) 0.0185(15) 0.0253(15) -0.0005(14) 0.0092(12) -0.0039(14) C22 0.0206(16) 0.0248(18) 0.0223(16) -0.0022(14) 0.0094(13) -0.0020(14) C41 0.0165(15) 0.0213(17) 0.0210(16) -0.0021(13) 0.0075(13) -0.0044(13) C10 0.0141(14) 0.0225(17) 0.0208(14) 0.0009(12) 0.0077(11) -0.0001(13) C11 0.0232(16) 0.0106(15) 0.0243(16) -0.0043(12) 0.0081(13) -0.0007(12) C19 0.0151(15) 0.0258(18) 0.0278(17) -0.0003(13) 0.0055(13) -0.0064(14) C39 0.0147(15) 0.0234(17) 0.0259(16) -0.0035(13) 0.0077(12) -0.0029(14) C38 0.0206(15) 0.0262(17) 0.0266(16) -0.0007(14) 0.0126(13) -0.0005(14) C42 0.0241(17) 0.0234(18) 0.0211(16) -0.0028(14) 0.0082(13) -0.0023(13) C34 0.0205(15) 0.0100(15) 0.0194(14) 0.0025(12) 0.0062(12) -0.0018(12) C44 0.0149(14) 0.0225(18) 0.0261(16) -0.0009(13) 0.0068(12) -0.0107(13) C20 0.0242(17) 0.0191(17) 0.0227(16) 0.0045(13) 0.0090(13) -0.0064(13) C17 0.0157(15) 0.0227(17) 0.0176(15) 0.0037(13) 0.0050(12) -0.0025(13) C43 0.0193(16) 0.0234(17) 0.0219(16) 0.0014(14) 0.0049(13) -0.0082(13) C16 0.0252(17) 0.0172(16) 0.0247(15) -0.0047(13) 0.0122(13) -0.0048(13) C37 0.0242(16) 0.0255(17) 0.0212(15) 0.0021(14) 0.0094(13) -0.0003(14) C24 0.0105(14) 0.0223(16) 0.0218(15) -0.0023(12) 0.0044(12) -0.0027(13) C21 0.0250(17) 0.0264(18) 0.0237(16) -0.0024(14) 0.0117(14) -0.0036(13) C25 0.0164(15) 0.0286(18) 0.0174(15) 0.0065(14) 0.0060(13) 0.0014(13) C46 0.0239(18) 0.051(2) 0.0256(18) -0.0047(16) 0.0015(15) 0.0007(17) C6 0.0172(16) 0.0188(16) 0.0254(16) 0.0025(13) 0.0065(13) -0.0011(13) C29 0.0195(16) 0.0151(16) 0.0266(17) -0.0020(13) 0.0076(13) 0.0005(13) C7 0.0136(15) 0.0235(17) 0.0272(17) -0.0029(13) 0.0087(13) -0.0034(13) C28 0.0188(15) 0.0119(15) 0.0210(15) -0.0026(12) 0.0068(12) 0.0034(12) C12 0.0253(17) 0.0195(17) 0.0292(17) -0.0018(13) 0.0136(14) 0.0001(13) C32 0.0347(18) 0.0226(17) 0.0213(16) -0.0052(15) 0.0092(14) -0.0011(14) C2 0.0224(16) 0.0198(17) 0.0187(15) 0.0073(13) 0.0064(13) 0.0028(13) C26 0.0209(16) 0.0219(17) 0.0198(15) 0.0073(13) 0.0069(13) 0.0039(13) C31 0.0243(17) 0.0210(17) 0.0254(17) -0.0100(13) -0.0017(13) 0.0048(14) C9 0.0175(14) 0.0214(17) 0.0212(15) 0.0007(12) 0.0046(12) 0.0023(12) C3 0.0263(17) 0.0151(15) 0.0234(16) 0.0032(13) 0.0099(14) 0.0018(13) C30 0.0210(16) 0.0170(16) 0.0291(18) -0.0028(13) 0.0078(14) 0.0048(14) C14 0.0214(16) 0.0204(17) 0.0337(18) -0.0036(13) 0.0058(14) -0.0039(14) C15 0.0196(16) 0.0214(17) 0.0365(18) -0.0032(13) 0.0122(14) -0.0046(14) C33 0.0220(16) 0.0178(16) 0.0259(16) -0.0042(12) 0.0094(13) 0.0008(13) C35 0.0161(15) 0.0165(16) 0.0274(16) -0.0020(12) 0.0075(13) -0.0004(13) C23 0.0274(18) 0.0275(19) 0.0278(17) 0.0062(15) 0.0031(14) -0.0018(14) C8 0.0232(15) 0.0215(16) 0.0193(14) -0.0067(14) 0.0068(12) -0.0025(13) C36 0.0207(16) 0.0213(17) 0.0245(16) -0.0004(13) 0.0033(13) 0.0021(13) C13 0.0296(18) 0.0218(17) 0.0253(16) -0.0014(14) 0.0087(14) -0.0038(13) C4 0.0203(15) 0.0145(16) 0.0210(15) -0.0017(12) 0.0104(12) 0.0004(12) C5 0.0132(14) 0.0163(16) 0.0204(15) -0.0037(12) 0.0065(12) -0.0042(12) C27 0.0178(15) 0.0170(16) 0.0184(15) -0.0005(12) 0.0060(12) 0.0024(13) C45 0.0222(15) 0.0150(15) 0.0226(15) -0.0009(14) 0.0108(12) -0.0049(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag S2 O3 . 1.432(2) ? S2 O4 . 1.4376(19) ? S2 N2 . 1.630(2) ? S2 C40 . 1.765(3) ? S1 O2 . 1.432(2) ? S1 O1 . 1.4321(19) ? S1 N1 . 1.624(2) ? S1 C17 . 1.769(3) ? Cl1 C8 . 1.741(3) ? Cl2 C31 . 1.749(3) ? N2 C24 . 1.497(3) ? N2 C27 . 1.515(4) ? N1 C1 . 1.487(3) ? N1 C4 . 1.508(4) ? C40 C41 . 1.396(4) ? C40 C45 . 1.396(4) ? C1 C2 . 1.500(4) ? C1 C5 . 1.512(4) ? C18 C17 . 1.387(4) ? C18 C19 . 1.390(4) ? C22 C21 . 1.376(4) ? C22 C17 . 1.391(4) ? C41 C42 . 1.385(4) ? C10 C9 . 1.381(4) ? C10 C5 . 1.387(4) ? C11 C12 . 1.383(4) ? C11 C16 . 1.388(4) ? C11 C4 . 1.517(4) ? C19 C20 . 1.392(4) ? C39 C38 . 1.384(4) ? C39 C34 . 1.396(4) ? C38 C37 . 1.392(4) ? C42 C43 . 1.402(4) ? C34 C35 . 1.385(4) ? C34 C24 . 1.514(4) ? C44 C45 . 1.376(4) ? C44 C43 . 1.391(4) ? C20 C21 . 1.397(4) ? C20 C23 . 1.507(4) ? C43 C46 . 1.494(4) ? C16 C15 . 1.389(4) ? C37 C36 . 1.386(4) ? C24 C25 . 1.511(4) ? C25 C26 . 1.312(4) ? C6 C7 . 1.377(4) ? C6 C5 . 1.398(4) ? C29 C30 . 1.380(4) ? C29 C28 . 1.395(4) ? C7 C8 . 1.380(4) ? C28 C33 . 1.386(4) ? C28 C27 . 1.519(4) ? C12 C13 . 1.390(4) ? C32 C31 . 1.380(4) ? C32 C33 . 1.387(4) ? C2 C3 . 1.315(4) ? C26 C27 . 1.495(4) ? C31 C30 . 1.376(4) ? C9 C8 . 1.381(4) ? C3 C4 . 1.499(4) ? C14 C13 . 1.383(4) ? C14 C15 . 1.384(4) ? C35 C36 . 1.384(4) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O3 S2 O4 . . 119.85(12) ? O3 S2 N2 . . 107.02(12) ? O4 S2 N2 . . 106.63(12) ? O3 S2 C40 . . 108.02(13) ? O4 S2 C40 . . 106.83(12) ? N2 S2 C40 . . 108.01(13) ? O2 S1 O1 . . 120.13(12) ? O2 S1 N1 . . 106.88(12) ? O1 S1 N1 . . 105.93(12) ? O2 S1 C17 . . 107.75(13) ? O1 S1 C17 . . 107.73(12) ? N1 S1 C17 . . 107.89(13) ? C24 N2 C27 . . 110.2(2) ? C24 N2 S2 . . 117.40(19) ? C27 N2 S2 . . 116.01(18) ? C1 N1 C4 . . 111.3(2) ? C1 N1 S1 . . 117.23(19) ? C4 N1 S1 . . 119.17(18) ? C41 C40 C45 . . 120.7(3) ? C41 C40 S2 . . 119.3(2) ? C45 C40 S2 . . 120.0(2) ? N1 C1 C2 . . 101.9(2) ? N1 C1 C5 . . 113.4(2) ? C2 C1 C5 . . 111.0(2) ? C17 C18 C19 . . 119.1(3) ? C21 C22 C17 . . 119.4(3) ? C42 C41 C40 . . 119.2(3) ? C9 C10 C5 . . 120.7(3) ? C12 C11 C16 . . 119.0(3) ? C12 C11 C4 . . 120.8(3) ? C16 C11 C4 . . 120.1(3) ? C18 C19 C20 . . 121.3(3) ? C38 C39 C34 . . 120.6(3) ? C39 C38 C37 . . 120.3(3) ? C41 C42 C43 . . 120.9(3) ? C35 C34 C39 . . 118.6(3) ? C35 C34 C24 . . 123.0(3) ? C39 C34 C24 . . 118.3(2) ? C45 C44 C43 . . 121.8(3) ? C19 C20 C21 . . 118.2(3) ? C19 C20 C23 . . 121.6(3) ? C21 C20 C23 . . 120.2(3) ? C18 C17 C22 . . 120.6(3) ? C18 C17 S1 . . 119.7(2) ? C22 C17 S1 . . 119.6(2) ? C44 C43 C42 . . 118.4(3) ? C44 C43 C46 . . 121.4(3) ? C42 C43 C46 . . 120.1(3) ? C11 C16 C15 . . 120.5(3) ? C36 C37 C38 . . 119.1(3) ? N2 C24 C25 . . 101.7(2) ? N2 C24 C34 . . 113.7(2) ? C25 C24 C34 . . 110.2(2) ? C22 C21 C20 . . 121.4(3) ? C26 C25 C24 . . 112.1(3) ? C7 C6 C5 . . 121.1(3) ? C30 C29 C28 . . 120.7(3) ? C6 C7 C8 . . 119.2(3) ? C33 C28 C29 . . 118.8(3) ? C33 C28 C27 . . 121.6(3) ? C29 C28 C27 . . 119.5(3) ? C11 C12 C13 . . 120.5(3) ? C31 C32 C33 . . 118.7(3) ? C3 C2 C1 . . 112.5(3) ? C25 C26 C27 . . 113.2(3) ? C30 C31 C32 . . 121.6(3) ? C30 C31 Cl2 . . 119.6(2) ? C32 C31 Cl2 . . 118.8(2) ? C10 C9 C8 . . 119.7(3) ? C2 C3 C4 . . 113.0(3) ? C31 C30 C29 . . 119.2(3) ? C13 C14 C15 . . 119.5(3) ? C14 C15 C16 . . 120.1(3) ? C28 C33 C32 . . 121.0(3) ? C36 C35 C34 . . 120.9(3) ? C7 C8 C9 . . 120.9(3) ? C7 C8 Cl1 . . 119.9(2) ? C9 C8 Cl1 . . 119.2(2) ? C35 C36 C37 . . 120.4(3) ? C14 C13 C12 . . 120.2(3) ? C3 C4 N1 . . 101.2(2) ? C3 C4 C11 . . 115.1(2) ? N1 C4 C11 . . 112.5(2) ? C10 C5 C6 . . 118.5(3) ? C10 C5 C1 . . 122.3(2) ? C6 C5 C1 . . 119.2(2) ? C26 C27 N2 . . 101.4(2) ? C26 C27 C28 . . 115.4(2) ? N2 C27 C28 . . 110.5(2) ? C44 C45 C40 . . 119.0(3) ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag O3 S2 N2 C24 . . . . 47.4(2) ? O4 S2 N2 C24 . . . . 176.81(19) ? C40 S2 N2 C24 . . . . -68.7(2) ? O3 S2 N2 C27 . . . . -179.30(19) ? O4 S2 N2 C27 . . . . -49.9(2) ? C40 S2 N2 C27 . . . . 64.6(2) ? O2 S1 N1 C1 . . . . -51.8(2) ? O1 S1 N1 C1 . . . . 179.01(19) ? C17 S1 N1 C1 . . . . 63.9(2) ? O2 S1 N1 C4 . . . . 169.19(19) ? O1 S1 N1 C4 . . . . 40.0(2) ? C17 S1 N1 C4 . . . . -75.2(2) ? O3 S2 C40 C41 . . . . 153.3(2) ? O4 S2 C40 C41 . . . . 23.1(3) ? N2 S2 C40 C41 . . . . -91.3(2) ? O3 S2 C40 C45 . . . . -28.3(3) ? O4 S2 C40 C45 . . . . -158.5(2) ? N2 S2 C40 C45 . . . . 87.1(3) ? C4 N1 C1 C2 . . . . 5.1(3) ? S1 N1 C1 C2 . . . . -137.0(2) ? C4 N1 C1 C5 . . . . -114.2(3) ? S1 N1 C1 C5 . . . . 103.7(2) ? C45 C40 C41 C42 . . . . -1.6(4) ? S2 C40 C41 C42 . . . . 176.8(2) ? C17 C18 C19 C20 . . . . -0.6(4) ? C34 C39 C38 C37 . . . . 0.3(5) ? C40 C41 C42 C43 . . . . 0.1(4) ? C38 C39 C34 C35 . . . . -1.0(4) ? C38 C39 C34 C24 . . . . 175.7(3) ? C18 C19 C20 C21 . . . . 2.3(4) ? C18 C19 C20 C23 . . . . -176.1(3) ? C19 C18 C17 C22 . . . . -1.6(4) ? C19 C18 C17 S1 . . . . 177.3(2) ? C21 C22 C17 C18 . . . . 2.1(4) ? C21 C22 C17 S1 . . . . -176.8(2) ? O2 S1 C17 C18 . . . . 17.2(3) ? O1 S1 C17 C18 . . . . 148.2(2) ? N1 S1 C17 C18 . . . . -97.9(3) ? O2 S1 C17 C22 . . . . -163.9(2) ? O1 S1 C17 C22 . . . . -32.9(3) ? N1 S1 C17 C22 . . . . 81.0(3) ? C45 C44 C43 C42 . . . . -0.8(4) ? C45 C44 C43 C46 . . . . 177.2(3) ? C41 C42 C43 C44 . . . . 1.1(4) ? C41 C42 C43 C46 . . . . -177.0(3) ? C12 C11 C16 C15 . . . . 0.4(4) ? C4 C11 C16 C15 . . . . -178.9(3) ? C39 C38 C37 C36 . . . . 0.3(5) ? C27 N2 C24 C25 . . . . -11.9(3) ? S2 N2 C24 C25 . . . . 124.0(2) ? C27 N2 C24 C34 . . . . 106.6(3) ? S2 N2 C24 C34 . . . . -117.6(2) ? C35 C34 C24 N2 . . . . -15.3(4) ? C39 C34 C24 N2 . . . . 168.2(3) ? C35 C34 C24 C25 . . . . 98.1(3) ? C39 C34 C24 C25 . . . . -78.4(3) ? C17 C22 C21 C20 . . . . -0.4(4) ? C19 C20 C21 C22 . . . . -1.8(4) ? C23 C20 C21 C22 . . . . 176.6(3) ? N2 C24 C25 C26 . . . . 8.2(3) ? C34 C24 C25 C26 . . . . -112.7(3) ? C5 C6 C7 C8 . . . . -0.9(4) ? C30 C29 C28 C33 . . . . -1.5(4) ? C30 C29 C28 C27 . . . . 175.8(3) ? C16 C11 C12 C13 . . . . 0.7(4) ? C4 C11 C12 C13 . . . . 180.0(3) ? N1 C1 C2 C3 . . . . -4.7(3) ? C5 C1 C2 C3 . . . . 116.3(3) ? C24 C25 C26 C27 . . . . -1.4(3) ? C33 C32 C31 C30 . . . . -1.1(4) ? C33 C32 C31 Cl2 . . . . 179.7(2) ? C5 C10 C9 C8 . . . . -1.8(4) ? C1 C2 C3 C4 . . . . 2.6(4) ? C32 C31 C30 C29 . . . . 1.7(4) ? Cl2 C31 C30 C29 . . . . -179.2(2) ? C28 C29 C30 C31 . . . . -0.3(4) ? C13 C14 C15 C16 . . . . 0.6(5) ? C11 C16 C15 C14 . . . . -1.0(5) ? C29 C28 C33 C32 . . . . 2.0(4) ? C27 C28 C33 C32 . . . . -175.2(3) ? C31 C32 C33 C28 . . . . -0.8(4) ? C39 C34 C35 C36 . . . . 1.0(4) ? C24 C34 C35 C36 . . . . -175.5(3) ? C6 C7 C8 C9 . . . . -0.3(4) ? C6 C7 C8 Cl1 . . . . -179.3(2) ? C10 C9 C8 C7 . . . . 1.6(4) ? C10 C9 C8 Cl1 . . . . -179.4(2) ? C34 C35 C36 C37 . . . . -0.4(4) ? C38 C37 C36 C35 . . . . -0.3(5) ? C15 C14 C13 C12 . . . . 0.4(5) ? C11 C12 C13 C14 . . . . -1.1(5) ? C2 C3 C4 N1 . . . . 0.7(3) ? C2 C3 C4 C11 . . . . -120.9(3) ? C1 N1 C4 C3 . . . . -3.8(3) ? S1 N1 C4 C3 . . . . 137.5(2) ? C1 N1 C4 C11 . . . . 119.6(2) ? S1 N1 C4 C11 . . . . -99.1(2) ? C12 C11 C4 C3 . . . . 39.1(4) ? C16 C11 C4 C3 . . . . -141.6(3) ? C12 C11 C4 N1 . . . . -76.1(3) ? C16 C11 C4 N1 . . . . 103.2(3) ? C9 C10 C5 C6 . . . . 0.5(4) ? C9 C10 C5 C1 . . . . 178.4(3) ? C7 C6 C5 C10 . . . . 0.8(4) ? C7 C6 C5 C1 . . . . -177.1(3) ? N1 C1 C5 C10 . . . . -3.5(4) ? C2 C1 C5 C10 . . . . -117.4(3) ? N1 C1 C5 C6 . . . . 174.4(2) ? C2 C1 C5 C6 . . . . 60.5(3) ? C25 C26 C27 N2 . . . . -6.0(3) ? C25 C26 C27 C28 . . . . 113.4(3) ? C24 N2 C27 C26 . . . . 11.2(3) ? S2 N2 C27 C26 . . . . -125.3(2) ? C24 N2 C27 C28 . . . . -111.7(3) ? S2 N2 C27 C28 . . . . 111.8(2) ? C33 C28 C27 C26 . . . . -19.1(4) ? C29 C28 C27 C26 . . . . 163.7(3) ? C33 C28 C27 N2 . . . . 95.2(3) ? C29 C28 C27 N2 . . . . -82.1(3) ? C43 C44 C45 C40 . . . . -0.6(4) ? C41 C40 C45 C44 . . . . 1.8(4) ? S2 C40 C45 C44 . . . . -176.5(2) ?