Electronic Supplementary Material for Organic & Biomolecular Chemistry This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'P.D. Beer' 'Rowena L. Paul' 'Matthew Vickers' 'Wallace W. H. Wong' _publ_contact_author_name 'Paul Beer' _publ_contact_author_address ; Inorganic Chemistry Department Oxford University South Parks Road Oxford OX1 3QR UNITED KINGDOM ; _publ_contact_author_email PAUL.BEER@CHEM.OX.AC.UK _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; Tetrakis(imidazolium)Macrocyclic Receptors for Anion Binding ; data_Compound_X _database_code_depnum_ccdc_archive 'CCDC 283001' #============================================================= # Diffractometer details #============================================================= _diffrn_measurement_device_type ; Nonius KappaCCD ; _diffrn_radiation_monochromator graphite _computing_data_collection ; KappaCCD software 'Collect' (Nonius, 2000) ; _computing_data_reduction ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; _computing_cell_refinement ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; #============================================================= # General computing #============================================================= _computing_structure_refinement ; CRYSTALS (Watkin et al, 2001) ; _computing_publication_material ; CRYSTALS (Watkin et al, 2001) ; _computing_structure_solution 'SIR92 (Giacovazzo et al, 1992)' _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_melting_point ? _refine_ls_matrix_type full _atom_sites_solution_primary direct _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment noref #============================================================= _cell_length_a 25.1991(4) _cell_angle_alpha 90 _cell_length_b 8.6736(2) _cell_angle_beta 90 _cell_length_c 12.6158(2) _cell_angle_gamma 90 _cell_volume 2757.40(9) _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P b c n ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,z x+1/2,-y+1/2,-z x,-y,z+1/2 -x,y,-z+1/2 -x+1/2,-y+1/2,z+1/2 x+1/2,y+1/2,-z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7997 0.0030 International_Tables_Vol_IV_Table_2.2B 'N ' 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 International_Tables_Vol_IV_Table_2.2B _cell_formula_units_Z 8 _chemical_formula_sum ' C17 H16 N4 ' _chemical_formula_moiety ' C17 H16 N4 ' _chemical_compound_source ; synthesis as described ; _chemical_formula_weight 276.34 _cell_measurement_reflns_used 3483 _cell_measurement_theta_min 5 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description ' prism ' _exptl_crystal_colour ' colourless ' _exptl_crystal_size_min 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_max 0.40 _exptl_crystal_density_diffrn 1.331 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 1168 _exptl_absorpt_coefficient_mu 0.082 _diffrn_measurement_method \w _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _exptl_absorpt_correction_T_min 0.97 _exptl_absorpt_correction_T_max 0.98 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 150 _diffrn_reflns_number 18754 _reflns_number_total 3142 #3564 unique reflections including absences _diffrn_reflns_av_R_equivalents 0.045 _diffrn_reflns_theta_min 5.143 _diffrn_reflns_theta_max 27.487 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.487 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _reflns_limit_h_min 0 _reflns_limit_h_max 32 _reflns_limit_k_min 0 _reflns_limit_k_max 11 _reflns_limit_l_min 0 _reflns_limit_l_max 16 _refine_diff_density_min -0.18 _refine_diff_density_max 0.16 _refine_ls_number_reflns 2021 _refine_ls_number_restraints 0 _refine_ls_number_parameters 190 #_refine_ls_R_factor_ref 0.0337 _refine_ls_wR_factor_ref 0.0381 _refine_ls_goodness_of_fit_ref 1.1219 #_reflns_number_all 3142 _refine_ls_R_factor_all 0.0612 _refine_ls_wR_factor_all 0.0596 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.00u(I) _reflns_number_gt 2021 _refine_ls_R_factor_gt 0.0337 _refine_ls_wR_factor_gt 0.0381 _refine_ls_shift/su_max 0.000347 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.528 0.262 0.252 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 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_occupancy _atom_site_adp_type N1 N 0.39260(4) 0.45428(12) 0.50743(9) 0.0242 1.0000 Uani C1 C 0.38108(5) 0.46956(17) 0.61232(11) 0.0295 1.0000 Uani N2 N 0.40646(5) 0.58189(15) 0.66008(9) 0.0315 1.0000 Uani C2 C 0.43814(5) 0.64496(16) 0.58071(11) 0.0257 1.0000 Uani C3 C 0.43013(5) 0.56620(15) 0.48478(10) 0.0227 1.0000 Uani C4 C 0.45850(5) 0.59933(16) 0.39287(11) 0.0261 1.0000 Uani C5 C 0.49582(6) 0.71602(16) 0.40039(12) 0.0300 1.0000 Uani C6 C 0.50405(6) 0.79692(16) 0.49515(13) 0.0315 1.0000 Uani C7 C 0.47556(6) 0.76314(16) 0.58591(12) 0.0304 1.0000 Uani C8 C 0.37029(5) 0.34111(16) 0.43448(11) 0.0262 1.0000 Uani N3 N 0.25854(4) 0.32058(14) 0.23427(9) 0.0282 1.0000 Uani C9 C 0.32181(5) 0.40021(15) 0.37512(11) 0.0250 1.0000 Uani N4 N 0.22057(5) 0.39813(16) 0.08179(10) 0.0380 1.0000 Uani C10 C 0.30005(6) 0.26992(16) 0.30687(11) 0.0295 1.0000 Uani C11 C 0.26351(6) 0.3449(2) 0.12792(12) 0.0361 1.0000 Uani C12 C 0.18398(6) 0.40989(16) 0.16403(11) 0.0284 1.0000 Uani C13 C 0.20699(5) 0.36106(15) 0.25967(11) 0.0247 1.0000 Uani C14 C 0.17934(6) 0.35737(16) 0.35494(11) 0.0288 1.0000 Uani C15 C 0.12681(6) 0.40336(18) 0.35157(12) 0.0325 1.0000 Uani C16 C 0.10326(6) 0.45302(16) 0.25693(13) 0.0336 1.0000 Uani C17 C 0.13103(6) 0.45800(17) 0.16291(12) 0.0330 1.0000 Uani H11 H 0.3554 0.4008 0.6499 0.0354 1.0000 Uiso H41 H 0.4523 0.5421 0.3252 0.0313 1.0000 Uiso H51 H 0.5174 0.7432 0.3366 0.0360 1.0000 Uiso H61 H 0.5312 0.8811 0.4972 0.0379 1.0000 Uiso H71 H 0.4816 0.8216 0.6531 0.0365 1.0000 Uiso H81 H 0.3981 0.3125 0.3815 0.0314 1.0000 Uiso H82 H 0.3598 0.2476 0.4759 0.0314 1.0000 Uiso H91 H 0.3321 0.4891 0.3291 0.0300 1.0000 Uiso H92 H 0.2941 0.4342 0.4269 0.0300 1.0000 Uiso H101 H 0.3299 0.2254 0.2644 0.0354 1.0000 Uiso H102 H 0.2851 0.1887 0.3545 0.0354 1.0000 Uiso H111 H 0.2971 0.3240 0.0883 0.0433 1.0000 Uiso H141 H 0.1965 0.3232 0.4224 0.0346 1.0000 Uiso H151 H 0.1052 0.4011 0.4180 0.0390 1.0000 Uiso H161 H 0.0652 0.4858 0.2576 0.0404 1.0000 Uiso H171 H 0.1139 0.4948 0.0961 0.0396 1.0000 Uiso loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0233(5) 0.0264(5) 0.0228(6) -0.0007(5) -0.0024(4) -0.0001(4) C1 0.0285(6) 0.0338(8) 0.0263(7) 0.0004(6) 0.0026(6) 0.0000(6) N2 0.0316(6) 0.0361(7) 0.0267(6) -0.0038(5) 0.0014(5) 0.0020(5) C2 0.0246(6) 0.0268(7) 0.0257(7) -0.0018(5) -0.0017(6) 0.0043(5) C3 0.0195(6) 0.0219(6) 0.0268(7) 0.0011(5) -0.0033(5) 0.0034(5) C4 0.0269(6) 0.0277(7) 0.0236(7) 0.0017(6) -0.0016(5) 0.0044(5) C5 0.0254(6) 0.0287(7) 0.0359(8) 0.0058(6) 0.0022(6) 0.0038(6) C6 0.0243(6) 0.0219(6) 0.0485(9) 0.0008(7) -0.0049(6) 0.0003(6) C7 0.0275(7) 0.0267(7) 0.0369(8) -0.0077(6) -0.0058(6) 0.0042(6) C8 0.0255(6) 0.0243(7) 0.0287(7) -0.0016(6) -0.0028(5) 0.0001(5) N3 0.0260(6) 0.0324(6) 0.0263(6) -0.0059(5) -0.0036(5) 0.0002(5) C9 0.0243(6) 0.0250(7) 0.0257(7) -0.0024(6) -0.0024(5) 0.0011(5) N4 0.0387(7) 0.0499(8) 0.0256(6) -0.0033(6) -0.0042(5) -0.0049(6) C10 0.0266(7) 0.0283(7) 0.0336(8) -0.0060(6) -0.0056(6) 0.0031(6) C11 0.0339(8) 0.0483(9) 0.0261(7) -0.0084(7) 0.0001(6) -0.0037(7) C12 0.0314(7) 0.0290(7) 0.0247(7) -0.0018(6) -0.0063(6) -0.0056(6) C13 0.0260(6) 0.0205(6) 0.0277(7) -0.0030(5) -0.0044(6) -0.0021(5) C14 0.0328(7) 0.0267(7) 0.0269(7) 0.0010(6) -0.0030(6) -0.0041(6) C15 0.0291(7) 0.0332(8) 0.0352(8) -0.0018(6) 0.0024(6) -0.0041(6) C16 0.0251(6) 0.0304(7) 0.0454(9) -0.0038(7) -0.0064(6) -0.0012(6) C17 0.0328(7) 0.0313(8) 0.0349(8) 0.0010(6) -0.0125(6) -0.0013(6) _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 . C1 . 1.3613(18) yes N1 . C3 . 1.3851(16) yes N1 . C8 . 1.4583(17) yes C1 . N2 . 1.3121(18) yes C1 . H11 . 1.000 no N2 . C2 . 1.3925(18) yes C2 . C3 . 1.4043(18) yes C2 . C7 . 1.394(2) yes C3 . C4 . 1.3921(19) yes C4 . C5 . 1.385(2) yes C4 . H41 . 1.000 no C5 . C6 . 1.402(2) yes C5 . H51 . 1.000 no C6 . C7 . 1.383(2) yes C6 . H61 . 1.000 no C7 . H71 . 1.000 no C8 . C9 . 1.5219(18) yes C8 . H81 . 1.000 no C8 . H82 . 1.000 no N3 . C10 . 1.4581(18) yes N3 . C11 . 1.3640(19) yes N3 . C13 . 1.3833(17) yes C9 . C10 . 1.5228(19) yes C9 . H91 . 1.000 no C9 . H92 . 1.000 no N4 . C11 . 1.312(2) yes N4 . C12 . 1.3917(19) yes C10 . H101 . 1.000 no C10 . H102 . 1.000 no C11 . H111 . 1.000 no C12 . C13 . 1.4040(19) yes C12 . C17 . 1.398(2) yes C13 . C14 . 1.3896(19) yes C14 . C15 . 1.383(2) yes C14 . H141 . 1.000 no C15 . C16 . 1.401(2) yes C15 . H151 . 1.000 no C16 . C17 . 1.378(2) yes C16 . H161 . 1.000 no C17 . H171 . 1.000 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 . N1 . C3 . 106.14(11) yes C1 . N1 . C8 . 126.64(12) yes C3 . N1 . C8 . 127.22(11) yes N1 . C1 . N2 . 114.50(12) yes N1 . C1 . H11 . 122.749 no N2 . C1 . H11 . 122.749 no C1 . N2 . C2 . 103.95(11) yes N2 . C2 . C3 . 110.26(12) yes N2 . C2 . C7 . 129.99(13) yes C3 . C2 . C7 . 119.69(13) yes N1 . C3 . C2 . 105.15(11) yes N1 . C3 . C4 . 131.84(12) yes C2 . C3 . C4 . 122.93(12) yes C3 . C4 . C5 . 116.26(13) yes C3 . C4 . H41 . 121.869 no C5 . C4 . H41 . 121.869 no C4 . C5 . C6 . 121.65(13) yes C4 . C5 . H51 . 119.172 no C6 . C5 . H51 . 119.173 no C5 . C6 . C7 . 121.55(13) yes C5 . C6 . H61 . 119.223 no C7 . C6 . H61 . 119.223 no C2 . C7 . C6 . 117.90(13) yes C2 . C7 . H71 . 121.048 no C6 . C7 . H71 . 121.048 no N1 . C8 . C9 . 113.15(11) yes N1 . C8 . H81 . 108.544 no C9 . C8 . H81 . 108.544 no N1 . C8 . H82 . 108.544 no C9 . C8 . H82 . 108.544 no H81 . C8 . H82 . 109.467 no C10 . N3 . C11 . 126.78(12) yes C10 . N3 . C13 . 127.21(12) yes C11 . N3 . C13 . 105.94(12) yes C8 . C9 . C10 . 108.50(11) yes C8 . C9 . H91 . 109.715 no C10 . C9 . H91 . 109.715 no C8 . C9 . H92 . 109.715 no C10 . C9 . H92 . 109.715 no H91 . C9 . H92 . 109.467 no C11 . N4 . C12 . 103.97(12) yes N3 . C10 . C9 . 112.95(11) yes N3 . C10 . H101 . 108.597 no C9 . C10 . H101 . 108.596 no N3 . C10 . H102 . 108.597 no C9 . C10 . H102 . 108.596 no H101 . C10 . H102 . 109.467 no N3 . C11 . N4 . 114.52(13) yes N3 . C11 . H111 . 122.740 no N4 . C11 . H111 . 122.740 no N4 . C12 . C13 . 110.18(12) yes N4 . C12 . C17 . 130.29(13) yes C13 . C12 . C17 . 119.52(13) yes N3 . C13 . C12 . 105.39(12) yes N3 . C13 . C14 . 131.71(12) yes C12 . C13 . C14 . 122.90(12) yes C13 . C14 . C15 . 116.53(13) yes C13 . C14 . H141 . 121.737 no C15 . C14 . H141 . 121.737 no C14 . C15 . C16 . 121.35(14) yes C14 . C15 . H151 . 119.325 no C16 . C15 . H151 . 119.325 no C15 . C16 . C17 . 121.87(13) yes C15 . C16 . H161 . 119.065 no C17 . C16 . H161 . 119.065 no C12 . C17 . C16 . 117.82(13) yes C12 . C17 . H171 . 121.090 no C16 . C17 . H171 . 121.090 no data_Compound_Xb _database_code_depnum_ccdc_archive 'CCDC 283002' #============================================================= # Diffractometer details #============================================================= _diffrn_measurement_device_type ; Nonius KappaCCD ; _diffrn_radiation_monochromator graphite _computing_data_collection ; KappaCCD software 'Collect' (Nonius, 2000) ; _computing_data_reduction ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; _computing_cell_refinement ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; #============================================================= # General computing #============================================================= _computing_structure_refinement ; CRYSTALS (Watkin et al, 2001) ; _computing_publication_material ; CRYSTALS (Watkin et al, 2001) ; _computing_structure_solution 'SIR92 (Giacovazzo et al, 1992)' _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_melting_point ? _refine_ls_matrix_type full _atom_sites_solution_primary direct _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment noref #============================================================= _cell_length_a 9.6741(2) _cell_angle_alpha 65.7093(10) _cell_length_b 12.6292(2) _cell_angle_beta 71.7542(9) _cell_length_c 13.1081(2) _cell_angle_gamma 83.9297(7) _cell_volume 1385.83(4) _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 International_Tables_Vol_IV_Table_2.2B 'F ' 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776 International_Tables_Vol_IV_Table_2.2B 'N ' 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 International_Tables_Vol_IV_Table_2.2B 'P ' 0.1023 0.0942 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645 1.1149 International_Tables_Vol_IV_Table_2.2B _cell_formula_units_Z 1 _chemical_formula_sum ' C46 H54 F24 N10 P4 ' _chemical_formula_moiety ' C42 H48 N8,2 (C2 H3 N),4(P F6)' _chemical_compound_source ; synthesis as described ; _chemical_formula_weight 1326.85 _cell_measurement_reflns_used 5835 _cell_measurement_theta_min 5 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description ' prism ' _exptl_crystal_colour ' colourless ' _exptl_crystal_size_min 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_max 0.32 _exptl_crystal_density_diffrn 1.590 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 676 _exptl_absorpt_coefficient_mu 0.262 _diffrn_measurement_method \w _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _exptl_absorpt_correction_T_min 0.92 _exptl_absorpt_correction_T_max 0.97 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 150 _diffrn_reflns_number 41262 _reflns_number_total 6294 _diffrn_reflns_av_R_equivalents 0.064 _diffrn_reflns_theta_min 5.108 _diffrn_reflns_theta_max 27.502 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.502 _diffrn_measured_fraction_theta_full 0.992 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _reflns_limit_h_min -11 _reflns_limit_h_max 12 _reflns_limit_k_min -14 _reflns_limit_k_max 16 _reflns_limit_l_min 0 _reflns_limit_l_max 16 _refine_diff_density_min -0.49 _refine_diff_density_max 0.62 _refine_ls_number_reflns 3552 _refine_ls_number_restraints 0 _refine_ls_number_parameters 379 #_refine_ls_R_factor_ref 0.0526 _refine_ls_wR_factor_ref 0.0611 _refine_ls_goodness_of_fit_ref 1.1089 #_reflns_number_all 6294 _refine_ls_R_factor_all 0.1081 _refine_ls_wR_factor_all 0.0940 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>2.00u(I) _reflns_number_gt 3552 _refine_ls_R_factor_gt 0.0526 _refine_ls_wR_factor_gt 0.0611 _refine_ls_shift/su_max 0.004330 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.963 0.698 0.660 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 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_occupancy _atom_site_adp_type N1 N 0.8890(3) 0.1436(2) 0.6177(2) 0.0327 1.0000 Uani C1 C 0.9090(3) 0.2465(3) 0.5263(3) 0.0317 1.0000 Uani N2 N 0.8757(3) 0.2381(2) 0.4383(2) 0.0310 1.0000 Uani C2 C 0.8801(3) 0.3344(3) 0.3260(3) 0.0316 1.0000 Uani C3 C 0.7277(3) 0.3684(3) 0.3172(3) 0.0298 1.0000 Uani C4 C 0.7369(3) 0.4684(3) 0.1994(3) 0.0337 1.0000 Uani N3 N 0.5933(3) 0.5049(2) 0.1867(2) 0.0301 1.0000 Uani C5 C 0.5257(4) 0.5989(3) 0.1990(3) 0.0333 1.0000 Uani N4 N 0.3958(3) 0.6080(2) 0.1834(2) 0.0346 1.0000 Uani C6 C 0.2868(4) 0.6982(3) 0.1864(3) 0.0431 1.0000 Uani C7 C 0.3436(4) 0.8017(3) 0.1921(3) 0.0398 1.0000 Uani C8 C 0.2354(4) 0.9004(3) 0.1723(3) 0.0416 1.0000 Uani C9 C 0.0906(4) 0.8794(3) 0.2682(3) 0.0372 1.0000 Uani C10 C 0.8418(3) 0.0634(3) 0.5870(3) 0.0331 1.0000 Uani C11 C 0.8324(3) 0.1230(3) 0.4737(3) 0.0319 1.0000 Uani C12 C 0.7884(4) 0.0682(3) 0.4156(3) 0.0392 1.0000 Uani C13 C 0.7548(4) -0.0485(3) 0.4767(3) 0.0464 1.0000 Uani C14 C 0.7645(4) -0.1099(3) 0.5910(3) 0.0445 1.0000 Uani C15 C 0.8077(4) -0.0555(3) 0.6486(3) 0.0389 1.0000 Uani C16 C 0.4994(3) 0.4481(3) 0.1633(2) 0.0303 1.0000 Uani C17 C 0.3743(4) 0.5139(3) 0.1606(3) 0.0326 1.0000 Uani C18 C 0.2567(4) 0.4839(3) 0.1365(3) 0.0384 1.0000 Uani C19 C 0.2709(4) 0.3855(3) 0.1150(3) 0.0443 1.0000 Uani C20 C 0.3962(5) 0.3190(3) 0.1166(3) 0.0457 1.0000 Uani C21 C 0.5130(4) 0.3478(3) 0.1413(3) 0.0378 1.0000 Uani P1 P 0.75055(10) 0.59148(7) 0.47681(7) 0.0354 1.0000 Uani F1 F 0.8002(3) 0.72421(19) 0.4155(2) 0.0646 1.0000 Uani F2 F 0.7094(4) 0.4562(2) 0.5359(3) 0.0833 1.0000 Uani F3 F 0.6054(3) 0.6158(3) 0.5571(3) 0.0835 1.0000 Uani F4 F 0.9004(3) 0.5644(3) 0.3987(3) 0.0930 1.0000 Uani F5 F 0.8259(3) 0.5731(2) 0.5749(2) 0.0626 1.0000 Uani F6 F 0.6780(3) 0.6102(2) 0.3778(2) 0.0629 1.0000 Uani P2 P 1.00815(9) 0.22736(7) 0.02190(7) 0.0316 1.0000 Uani F7 F 0.9969(2) 0.35721(17) 0.0147(2) 0.0501 1.0000 Uani F8 F 1.0195(3) 0.09761(18) 0.0312(2) 0.0591 1.0000 Uani F9 F 0.8354(2) 0.2142(2) 0.0707(2) 0.0632 1.0000 Uani F10 F 1.1817(2) 0.24286(19) -0.0278(2) 0.0477 1.0000 Uani F11 F 1.0181(3) 0.1825(2) 0.15252(18) 0.0573 1.0000 Uani F12 F 1.0011(3) 0.2732(2) -0.1085(2) 0.0660 1.0000 Uani N5 N 0.5332(5) 0.0669(4) 0.1115(5) 0.0898 1.0000 Uani C22 C 0.6130(5) 0.0020(4) 0.1516(4) 0.0557 1.0000 Uani C23 C 0.7146(6) -0.0789(4) 0.1954(4) 0.0690 1.0000 Uani H11 H 0.9440 0.3194 0.5240 0.0374 1.0000 Uiso H21 H 0.9315 0.4029 0.3189 0.0366 1.0000 Uiso H22 H 0.9343 0.3101 0.2608 0.0366 1.0000 Uiso H31 H 0.6730 0.3932 0.3819 0.0359 1.0000 Uiso H32 H 0.6758 0.3002 0.3241 0.0359 1.0000 Uiso H41 H 0.7900 0.5358 0.1929 0.0393 1.0000 Uiso H42 H 0.7917 0.4428 0.1353 0.0393 1.0000 Uiso H51 H 0.5681 0.6552 0.2175 0.0417 1.0000 Uiso H61 H 0.2011 0.6633 0.2571 0.0545 1.0000 Uiso H62 H 0.2555 0.7254 0.1140 0.0545 1.0000 Uiso H71 H 0.3572 0.7787 0.2709 0.0492 1.0000 Uiso H72 H 0.4391 0.8288 0.1300 0.0492 1.0000 Uiso H81 H 0.2832 0.9711 0.1640 0.0497 1.0000 Uiso H82 H 0.2143 0.9152 0.0977 0.0497 1.0000 Uiso H91 H 0.0301 0.9498 0.2463 0.0463 1.0000 Uiso H92 H 0.0391 0.8109 0.2755 0.0463 1.0000 Uiso H121 H 0.7817 0.1114 0.3341 0.0481 1.0000 Uiso H131 H 0.7223 -0.0913 0.4385 0.0578 1.0000 Uiso H141 H 0.7395 -0.1949 0.6315 0.0513 1.0000 Uiso H151 H 0.8142 -0.0988 0.7302 0.0454 1.0000 Uiso H181 H 0.1674 0.5316 0.1351 0.0458 1.0000 Uiso H191 H 0.1894 0.3603 0.0976 0.0542 1.0000 Uiso H201 H 0.4017 0.2483 0.0994 0.0549 1.0000 Uiso H211 H 0.6017 0.2994 0.1433 0.0449 1.0000 Uiso H231 H 0.6626 -0.1535 0.2548 0.0829 1.0000 Uiso H232 H 0.7654 -0.0470 0.2329 0.0829 1.0000 Uiso H233 H 0.7878 -0.0932 0.1294 0.0829 1.0000 Uiso loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0334(14) 0.0302(13) 0.0372(14) -0.0136(11) -0.0151(11) 0.0041(11) C1 0.0306(16) 0.0268(15) 0.0361(17) -0.0093(13) -0.0129(13) 0.0026(12) N2 0.0332(14) 0.0263(12) 0.0349(14) -0.0120(11) -0.0131(11) 0.0033(10) C2 0.0316(17) 0.0313(16) 0.0287(15) -0.0100(13) -0.0073(13) 0.0003(12) C3 0.0295(16) 0.0307(15) 0.0296(15) -0.0114(12) -0.0102(12) 0.0005(12) C4 0.0314(17) 0.0335(16) 0.0334(16) -0.0098(13) -0.0104(13) -0.0004(13) N3 0.0330(14) 0.0309(13) 0.0276(13) -0.0103(10) -0.0126(11) 0.0014(10) C5 0.0370(18) 0.0289(15) 0.0385(17) -0.0129(13) -0.0182(14) 0.0018(13) N4 0.0392(16) 0.0327(14) 0.0399(15) -0.0168(12) -0.0211(12) 0.0065(11) C6 0.0393(19) 0.0441(19) 0.053(2) -0.0203(16) -0.0245(17) 0.0099(15) C7 0.0398(19) 0.0398(18) 0.0435(19) -0.0190(15) -0.0155(15) 0.0054(14) C8 0.047(2) 0.0376(18) 0.0393(18) -0.0157(15) -0.0146(16) 0.0096(15) C9 0.043(2) 0.0346(17) 0.0381(18) -0.0127(14) -0.0223(15) 0.0066(14) C10 0.0347(17) 0.0293(15) 0.0360(17) -0.0131(13) -0.0120(13) 0.0032(13) C11 0.0339(17) 0.0265(15) 0.0340(16) -0.0109(12) -0.0109(13) 0.0043(12) C12 0.049(2) 0.0354(17) 0.0356(18) -0.0161(14) -0.0135(15) 0.0003(15) C13 0.061(2) 0.0387(19) 0.045(2) -0.0217(16) -0.0139(17) -0.0040(17) C14 0.056(2) 0.0272(16) 0.045(2) -0.0123(15) -0.0097(17) -0.0033(15) C15 0.044(2) 0.0312(17) 0.0379(18) -0.0111(14) -0.0129(15) 0.0042(14) C16 0.0372(17) 0.0315(15) 0.0215(14) -0.0097(12) -0.0075(12) -0.0035(12) C17 0.0399(18) 0.0326(15) 0.0309(16) -0.0151(13) -0.0143(13) -0.0003(13) C18 0.0382(19) 0.0444(19) 0.0320(16) -0.0122(14) -0.0115(14) -0.0058(14) C19 0.049(2) 0.052(2) 0.0346(18) -0.0163(16) -0.0113(16) -0.0173(17) C20 0.066(3) 0.0377(18) 0.0334(18) -0.0137(15) -0.0107(17) -0.0142(17) C21 0.049(2) 0.0323(17) 0.0315(16) -0.0130(14) -0.0095(14) -0.0008(14) P1 0.0399(5) 0.0332(4) 0.0355(5) -0.0140(4) -0.0131(4) -0.0020(3) F1 0.0883(19) 0.0396(12) 0.0693(16) -0.0111(11) -0.0377(14) -0.0138(12) F2 0.140(3) 0.0435(14) 0.0718(17) -0.0073(12) -0.0534(18) -0.0202(15) F3 0.0463(15) 0.124(3) 0.0738(18) -0.0452(18) -0.0068(13) 0.0176(15) F4 0.080(2) 0.115(3) 0.0703(18) -0.0424(17) -0.0110(15) 0.0450(18) F5 0.0670(16) 0.0710(16) 0.0500(13) -0.0101(12) -0.0312(12) -0.0155(12) F6 0.0872(18) 0.0563(14) 0.0570(14) -0.0140(11) -0.0451(13) -0.0095(12) P2 0.0339(5) 0.0304(4) 0.0346(4) -0.0131(3) -0.0151(3) -0.0004(3) F7 0.0509(13) 0.0314(10) 0.0660(14) -0.0196(10) -0.0160(11) 0.0053(9) F8 0.0684(15) 0.0393(12) 0.0781(16) -0.0332(12) -0.0180(12) -0.0041(10) F9 0.0327(12) 0.0677(15) 0.0854(18) -0.0328(13) -0.0077(11) -0.0047(10) F10 0.0330(11) 0.0535(12) 0.0638(13) -0.0299(11) -0.0156(9) 0.0033(9) F11 0.0804(17) 0.0564(14) 0.0361(11) -0.0157(10) -0.0248(11) 0.0086(12) F12 0.0714(17) 0.0916(19) 0.0447(13) -0.0264(12) -0.0337(12) 0.0100(13) N5 0.067(3) 0.072(3) 0.122(4) -0.030(3) -0.030(3) 0.005(2) C22 0.048(2) 0.049(2) 0.071(3) -0.026(2) -0.014(2) -0.0045(19) C23 0.076(3) 0.065(3) 0.066(3) -0.022(2) -0.030(2) 0.009(2) _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 . C1 . 1.337(4) yes N1 . C9 2_666 1.475(4) yes N1 . C10 . 1.394(4) yes C1 . N2 . 1.335(4) yes C1 . H11 . 1.000 no N2 . C2 . 1.465(4) yes N2 . C11 . 1.398(4) yes C2 . C3 . 1.518(4) yes C2 . H21 . 1.000 no C2 . H22 . 1.000 no C3 . C4 . 1.523(4) yes C3 . H31 . 1.000 no C3 . H32 . 1.000 no C4 . N3 . 1.455(4) yes C4 . H41 . 1.000 no C4 . H42 . 1.000 no N3 . C5 . 1.338(4) yes N3 . C16 . 1.388(4) yes C5 . N4 . 1.321(4) yes C5 . H51 . 1.000 no N4 . C6 . 1.473(4) yes N4 . C17 . 1.389(4) yes C6 . C7 . 1.507(5) yes C6 . H61 . 1.000 no C6 . H62 . 1.000 no C7 . C8 . 1.532(5) yes C7 . H71 . 1.000 no C7 . H72 . 1.000 no C8 . C9 . 1.521(5) yes C8 . H81 . 1.000 no C8 . H82 . 1.000 no C9 . H91 . 1.000 no C9 . H92 . 1.000 no C10 . C11 . 1.390(4) yes C10 . C15 . 1.399(5) yes C11 . C12 . 1.392(5) yes C12 . C13 . 1.374(5) yes C12 . H121 . 1.000 no C13 . C14 . 1.403(5) yes C13 . H131 . 1.000 no C14 . C15 . 1.379(5) yes C14 . H141 . 1.000 no C15 . H151 . 1.000 no C16 . C17 . 1.394(4) yes C16 . C21 . 1.396(4) yes C17 . C18 . 1.397(4) yes C18 . C19 . 1.368(5) yes C18 . H181 . 1.000 no C19 . C20 . 1.401(6) yes C19 . H191 . 1.000 no C20 . C21 . 1.387(5) yes C20 . H201 . 1.000 no C21 . H211 . 1.000 no P1 . F1 . 1.583(2) yes P1 . F2 . 1.593(3) yes P1 . F3 . 1.557(3) yes P1 . F4 . 1.588(3) yes P1 . F5 . 1.595(2) yes P1 . F6 . 1.586(2) yes P2 . F7 . 1.597(2) yes P2 . F8 . 1.587(2) yes P2 . F9 . 1.591(2) yes P2 . F10 . 1.601(2) yes P2 . F11 . 1.599(2) yes P2 . F12 . 1.585(2) yes N5 . C22 . 1.145(6) yes C22 . C23 . 1.413(7) yes C23 . H231 . 1.000 no C23 . H232 . 1.000 no C23 . H233 . 1.000 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 . N1 . C9 2_666 125.7(3) yes C1 . N1 . C10 . 108.0(3) yes C9 2_666 N1 . C10 . 126.3(3) yes N1 . C1 . N2 . 110.4(3) yes N1 . C1 . H11 . 124.815 no N2 . C1 . H11 . 124.815 no C1 . N2 . C2 . 125.4(3) yes C1 . N2 . C11 . 108.2(2) yes C2 . N2 . C11 . 126.4(2) yes N2 . C2 . C3 . 111.2(2) yes N2 . C2 . H21 . 109.050 no C3 . C2 . H21 . 109.050 no N2 . C2 . H22 . 109.050 no C3 . C2 . H22 . 109.050 no H21 . C2 . H22 . 109.467 no C2 . C3 . C4 . 109.5(2) yes C2 . C3 . H31 . 109.457 no C4 . C3 . H31 . 109.457 no C2 . C3 . H32 . 109.457 no C4 . C3 . H32 . 109.457 no H31 . C3 . H32 . 109.467 no C3 . C4 . N3 . 111.7(2) yes C3 . C4 . H41 . 108.902 no N3 . C4 . H41 . 108.902 no C3 . C4 . H42 . 108.902 no N3 . C4 . H42 . 108.902 no H41 . C4 . H42 . 109.467 no C4 . N3 . C5 . 125.7(3) yes C4 . N3 . C16 . 127.0(3) yes C5 . N3 . C16 . 107.2(3) yes N3 . C5 . N4 . 111.4(3) yes N3 . C5 . H51 . 124.285 no N4 . C5 . H51 . 124.285 no C5 . N4 . C6 . 129.6(3) yes C5 . N4 . C17 . 107.7(3) yes C6 . N4 . C17 . 122.7(3) yes N4 . C6 . C7 . 113.1(3) yes N4 . C6 . H61 . 108.551 no C7 . C6 . H61 . 108.551 no N4 . C6 . H62 . 108.551 no C7 . C6 . H62 . 108.551 no H61 . C6 . H62 . 109.467 no C6 . C7 . C8 . 110.1(3) yes C6 . C7 . H71 . 109.318 no C8 . C7 . H71 . 109.318 no C6 . C7 . H72 . 109.318 no C8 . C7 . H72 . 109.318 no H71 . C7 . H72 . 109.467 no C7 . C8 . C9 . 116.2(3) yes C7 . C8 . H81 . 107.761 no C9 . C8 . H81 . 107.761 no C7 . C8 . H82 . 107.761 no C9 . C8 . H82 . 107.761 no H81 . C8 . H82 . 109.467 no N1 2_666 C9 . C8 . 111.6(3) yes N1 2_666 C9 . H91 . 108.933 no C8 . C9 . H91 . 108.933 no N1 2_666 C9 . H92 . 108.933 no C8 . C9 . H92 . 108.933 no H91 . C9 . H92 . 109.467 no N1 . C10 . C11 . 107.0(3) yes N1 . C10 . C15 . 131.5(3) yes C11 . C10 . C15 . 121.4(3) yes N2 . C11 . C10 . 106.4(3) yes N2 . C11 . C12 . 131.4(3) yes C10 . C11 . C12 . 122.1(3) yes C11 . C12 . C13 . 116.1(3) yes C11 . C12 . H121 . 121.929 no C13 . C12 . H121 . 121.929 no C12 . C13 . C14 . 122.3(3) yes C12 . C13 . H131 . 118.832 no C14 . C13 . H131 . 118.832 no C13 . C14 . C15 . 121.5(3) yes C13 . C14 . H141 . 119.244 no C15 . C14 . H141 . 119.244 no C10 . C15 . C14 . 116.5(3) yes C10 . C15 . H151 . 121.764 no C14 . C15 . H151 . 121.764 no N3 . C16 . C17 . 106.8(3) yes N3 . C16 . C21 . 132.3(3) yes C17 . C16 . C21 . 120.9(3) yes N4 . C17 . C16 . 106.8(3) yes N4 . C17 . C18 . 130.5(3) yes C16 . C17 . C18 . 122.7(3) yes C17 . C18 . C19 . 116.0(3) yes C17 . C18 . H181 . 121.992 no C19 . C18 . H181 . 121.992 no C18 . C19 . C20 . 121.9(3) yes C18 . C19 . H191 . 119.027 no C20 . C19 . H191 . 119.027 no C19 . C20 . C21 . 122.3(3) yes C19 . C20 . H201 . 118.833 no C21 . C20 . H201 . 118.833 no C16 . C21 . C20 . 116.1(3) yes C16 . C21 . H211 . 121.964 no C20 . C21 . H211 . 121.964 no F1 . P1 . F2 . 176.94(18) yes F1 . P1 . F3 . 92.38(17) yes F2 . P1 . F3 . 90.55(19) yes F1 . P1 . F4 . 88.32(18) yes F2 . P1 . F4 . 88.73(19) yes F3 . P1 . F4 . 178.08(17) yes F1 . P1 . F5 . 89.61(13) yes F2 . P1 . F5 . 89.57(14) yes F3 . P1 . F5 . 88.77(16) yes F4 . P1 . F5 . 89.44(16) yes F1 . P1 . F6 . 90.02(13) yes F2 . P1 . F6 . 90.76(14) yes F3 . P1 . F6 . 92.02(16) yes F4 . P1 . F6 . 89.77(17) yes F5 . P1 . F6 . 179.14(15) yes F7 . P2 . F8 . 179.04(14) yes F7 . P2 . F9 . 89.41(13) yes F8 . P2 . F9 . 90.59(13) yes F7 . P2 . F10 . 89.67(11) yes F8 . P2 . F10 . 90.33(13) yes F9 . P2 . F10 . 179.05(13) yes F7 . P2 . F11 . 89.16(12) yes F8 . P2 . F11 . 89.87(13) yes F9 . P2 . F11 . 90.37(14) yes F10 . P2 . F11 . 89.86(13) yes F7 . P2 . F12 . 90.36(14) yes F8 . P2 . F12 . 90.60(14) yes F9 . P2 . F12 . 90.59(14) yes F10 . P2 . F12 . 89.17(13) yes F11 . P2 . F12 . 178.93(14) yes N5 . C22 . C23 . 176.9(6) yes C22 . C23 . H231 . 109.467 no C22 . C23 . H232 . 109.467 no H231 . C23 . H232 . 109.476 no C22 . C23 . H233 . 109.466 no H231 . C23 . H233 . 109.476 no H232 . C23 . H233 . 109.476 no