# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_coden_Cambridge 182 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'F Gabbai' 'Todd W Hudnall' _publ_contact_author_name 'F Gabbai' _publ_contact_author_email FRANCOIS@TAMU.EDU _publ_section_title ; A BODIPY boronium cation for the sensing of fluoride ions ; # Attachment 't.cif' data_t _database_code_depnum_ccdc_archive 'CCDC 689181' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Bodipy-BFOTf _chemical_melting_point ? _chemical_formula_moiety C14H17N2-B{F}{SO3CF3} _chemical_formula_sum 'C15 H17 B F4 N2 O3 S' _chemical_formula_weight 392.18 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.715(4) _cell_length_b 11.143(4) _cell_length_c 14.078(5) _cell_angle_alpha 90.00 _cell_angle_beta 91.037(7) _cell_angle_gamma 90.00 _cell_volume 1680.7(10) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max .322 _exptl_crystal_size_mid .262 _exptl_crystal_size_min .130 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.550 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.253 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details none _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10057 _diffrn_reflns_av_R_equivalents 0.0842 _diffrn_reflns_av_sigmaI/netI 0.0675 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 28.43 _reflns_number_total 4022 _reflns_number_gt 2959 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART-97' _computing_cell_refinement SAINT-97 _computing_data_reduction SAINT-97 _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1099P)^2^+0.2441P] 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 4022 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0693 _refine_ls_R_factor_gt 0.0517 _refine_ls_wR_factor_ref 0.1710 _refine_ls_wR_factor_gt 0.1574 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.007 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.82313(5) 0.03147(5) 0.21689(4) 0.01836(18) Uani 1 1 d . . . F1 F 0.82437(13) 0.05497(12) 0.48325(9) 0.0204(3) Uani 1 1 d . . . O1 O 0.84834(15) 0.04098(14) 0.32228(11) 0.0188(4) Uani 1 1 d . . . F2 F 0.96392(17) -0.15975(15) 0.21956(13) 0.0400(4) Uani 1 1 d . . . O2 O 0.72054(16) -0.04471(16) 0.19410(12) 0.0250(4) Uani 1 1 d . . . F3 F 0.96686(17) -0.05931(17) 0.08928(11) 0.0434(5) Uani 1 1 d . . . N1 N 0.63758(17) 0.08954(16) 0.38981(13) 0.0162(4) Uani 1 1 d . . . N2 N 0.72261(17) -0.11436(17) 0.41025(13) 0.0168(4) Uani 1 1 d . . . F4 F 1.06552(14) 0.00608(18) 0.21256(14) 0.0444(5) Uani 1 1 d . . . C4 C 0.5196(2) 0.04005(19) 0.37131(15) 0.0154(4) Uani 1 1 d . . . C6 C 0.6030(2) -0.16140(19) 0.39166(15) 0.0161(4) Uani 1 1 d . . . C12 C 0.3773(2) -0.1366(2) 0.34541(17) 0.0214(5) Uani 1 1 d . . . H12A H 0.3812 -0.2226 0.3477 0.032 Uiso 1 1 calc R . . H12B H 0.3526 -0.1114 0.2826 0.032 Uiso 1 1 calc R . . H12C H 0.3175 -0.1085 0.3902 0.032 Uiso 1 1 calc R . . C1 C 0.6278(2) 0.2109(2) 0.38834(16) 0.0179(5) Uani 1 1 d . . . C5 C 0.5030(2) -0.08549(19) 0.36990(15) 0.0157(4) Uani 1 1 d . . . C3 C 0.4340(2) 0.1366(2) 0.35826(16) 0.0177(5) Uani 1 1 d . . . O3 O 0.83280(19) 0.14485(17) 0.17199(14) 0.0321(5) Uani 1 1 d . . . C15 C 0.9637(2) -0.0503(2) 0.18325(19) 0.0263(5) Uani 1 1 d . . . C13 C 0.5111(2) -0.3817(2) 0.39542(18) 0.0230(5) Uani 1 1 d . . . H13A H 0.5461 -0.4592 0.4092 0.035 Uiso 1 1 calc R . . H13B H 0.4774 -0.3810 0.3318 0.035 Uiso 1 1 calc R . . H13C H 0.4459 -0.3647 0.4393 0.035 Uiso 1 1 calc R . . C2 C 0.5032(2) 0.2412(2) 0.36955(16) 0.0190(5) Uani 1 1 d . . . H2B H 0.4718 0.3188 0.3653 0.023 Uiso 1 1 calc R . . C14 C 0.9357(2) -0.1880(2) 0.45775(19) 0.0256(5) Uani 1 1 d . . . H14A H 0.9562 -0.1044 0.4530 0.038 Uiso 1 1 calc R . . H14B H 0.9862 -0.2333 0.4149 0.038 Uiso 1 1 calc R . . H14C H 0.9513 -0.2150 0.5216 0.038 Uiso 1 1 calc R . . C8 C 0.7334(2) -0.3127(2) 0.43053(17) 0.0218(5) Uani 1 1 d . . . H8A H 0.7655 -0.3884 0.4443 0.026 Uiso 1 1 calc R . . B1 B 0.7561(2) 0.0175(2) 0.40552(18) 0.0172(5) Uani 1 1 d . . . C10 C 0.7366(2) 0.2921(2) 0.40455(18) 0.0233(5) Uani 1 1 d . . . H10A H 0.8104 0.2450 0.4160 0.035 Uiso 1 1 calc R . . H10B H 0.7217 0.3422 0.4587 0.035 Uiso 1 1 calc R . . H10C H 0.7479 0.3414 0.3495 0.035 Uiso 1 1 calc R . . C9 C 0.8012(2) -0.2058(2) 0.43248(16) 0.0199(5) Uani 1 1 d . . . C11 C 0.2969(2) 0.1349(2) 0.33626(18) 0.0235(5) Uani 1 1 d . . . H11A H 0.2665 0.2157 0.3316 0.035 Uiso 1 1 calc R . . H11B H 0.2543 0.0936 0.3860 0.035 Uiso 1 1 calc R . . H11C H 0.2820 0.0942 0.2770 0.035 Uiso 1 1 calc R . . C7 C 0.6106(2) -0.2884(2) 0.40480(16) 0.0180(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0176(3) 0.0169(3) 0.0208(3) 0.0008(2) 0.0039(2) 0.0008(2) F1 0.0196(7) 0.0192(7) 0.0224(7) -0.0034(5) -0.0016(5) -0.0029(5) O1 0.0159(8) 0.0201(8) 0.0205(8) -0.0011(6) 0.0025(6) -0.0024(6) F2 0.0424(10) 0.0265(8) 0.0513(11) 0.0008(7) 0.0071(8) 0.0150(7) O2 0.0204(9) 0.0296(10) 0.0251(9) -0.0033(7) 0.0002(7) -0.0028(7) F3 0.0450(11) 0.0579(11) 0.0276(9) -0.0092(8) 0.0131(8) 0.0114(9) N1 0.0169(9) 0.0128(9) 0.0190(9) -0.0005(7) 0.0037(7) -0.0018(7) N2 0.0162(9) 0.0156(9) 0.0185(9) 0.0009(7) 0.0006(7) -0.0010(7) F4 0.0173(8) 0.0578(12) 0.0584(12) -0.0187(9) 0.0071(7) -0.0053(8) C4 0.0170(11) 0.0156(10) 0.0137(10) -0.0007(8) 0.0023(8) -0.0023(8) C6 0.0196(11) 0.0136(10) 0.0152(10) -0.0015(8) 0.0034(8) -0.0034(9) C12 0.0197(11) 0.0189(11) 0.0257(12) -0.0032(9) 0.0013(9) -0.0030(9) C1 0.0219(11) 0.0146(10) 0.0173(10) 0.0000(8) 0.0050(9) 0.0003(9) C5 0.0186(11) 0.0173(10) 0.0114(10) -0.0017(8) 0.0027(8) -0.0030(9) C3 0.0212(11) 0.0180(11) 0.0142(10) 0.0004(8) 0.0033(9) 0.0000(9) O3 0.0385(11) 0.0230(9) 0.0349(11) 0.0099(8) 0.0054(8) 0.0023(8) C15 0.0223(12) 0.0278(13) 0.0289(13) -0.0051(10) 0.0051(10) 0.0022(10) C13 0.0270(13) 0.0157(11) 0.0265(12) -0.0024(9) 0.0048(10) -0.0039(10) C2 0.0222(12) 0.0146(10) 0.0203(11) 0.0005(9) 0.0031(9) 0.0023(9) C14 0.0209(12) 0.0243(12) 0.0316(13) 0.0020(10) 0.0014(10) 0.0042(10) C8 0.0278(13) 0.0154(11) 0.0223(11) -0.0009(9) 0.0024(10) 0.0044(9) B1 0.0171(12) 0.0147(12) 0.0198(12) -0.0013(9) 0.0027(10) -0.0008(10) C10 0.0241(12) 0.0151(11) 0.0310(13) -0.0010(9) 0.0033(10) -0.0038(9) C9 0.0218(12) 0.0195(11) 0.0184(11) -0.0001(9) 0.0027(9) 0.0024(9) C11 0.0198(12) 0.0247(12) 0.0260(12) 0.0031(10) 0.0007(10) 0.0023(10) C7 0.0242(12) 0.0138(10) 0.0163(10) -0.0019(8) 0.0049(9) -0.0005(9) _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 S1 O3 1.4173(19) . ? S1 O2 1.4211(18) . ? S1 O1 1.5069(18) . ? S1 C15 1.830(3) . ? F1 B1 1.370(3) . ? O1 B1 1.568(3) . ? F2 C15 1.322(3) . ? F3 C15 1.328(3) . ? N1 C1 1.357(3) . ? N1 C4 1.400(3) . ? N1 B1 1.515(3) . ? N2 C9 1.355(3) . ? N2 C6 1.405(3) . ? N2 B1 1.515(3) . ? F4 C15 1.319(3) . ? C4 C5 1.410(3) . ? C4 C3 1.423(3) . ? C6 C5 1.395(3) . ? C6 C7 1.429(3) . ? C12 C5 1.497(3) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C1 C2 1.397(3) . ? C1 C10 1.490(3) . ? C3 C2 1.390(3) . ? C3 C11 1.496(3) . ? C13 C7 1.493(3) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C2 H2B 0.9300 . ? C14 C9 1.492(3) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C8 C7 1.385(3) . ? C8 C9 1.395(3) . ? C8 H8A 0.9300 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 S1 O2 119.62(12) . . ? O3 S1 O1 111.30(11) . . ? O2 S1 O1 112.86(10) . . ? O3 S1 C15 105.15(12) . . ? O2 S1 C15 106.32(12) . . ? O1 S1 C15 98.98(11) . . ? S1 O1 B1 128.30(15) . . ? C1 N1 C4 108.71(18) . . ? C1 N1 B1 126.47(19) . . ? C4 N1 B1 124.80(18) . . ? C9 N2 C6 108.86(19) . . ? C9 N2 B1 126.4(2) . . ? C6 N2 B1 124.75(19) . . ? N1 C4 C5 120.4(2) . . ? N1 C4 C3 107.69(19) . . ? C5 C4 C3 131.9(2) . . ? C5 C6 N2 120.63(19) . . ? C5 C6 C7 132.1(2) . . ? N2 C6 C7 107.2(2) . . ? C5 C12 H12A 109.5 . . ? C5 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C5 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N1 C1 C2 108.5(2) . . ? N1 C1 C10 122.9(2) . . ? C2 C1 C10 128.7(2) . . ? C6 C5 C4 120.1(2) . . ? C6 C5 C12 120.3(2) . . ? C4 C5 C12 119.6(2) . . ? C2 C3 C4 106.2(2) . . ? C2 C3 C11 123.7(2) . . ? C4 C3 C11 130.2(2) . . ? F4 C15 F2 108.8(2) . . ? F4 C15 F3 108.2(2) . . ? F2 C15 F3 108.4(2) . . ? F4 C15 S1 111.23(18) . . ? F2 C15 S1 110.80(18) . . ? F3 C15 S1 109.37(18) . . ? C7 C13 H13A 109.5 . . ? C7 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C7 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C3 C2 C1 109.0(2) . . ? C3 C2 H2B 125.5 . . ? C1 C2 H2B 125.5 . . ? C9 C14 H14A 109.5 . . ? C9 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C9 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C7 C8 C9 109.3(2) . . ? C7 C8 H8A 125.4 . . ? C9 C8 H8A 125.4 . . ? F1 B1 N2 112.57(19) . . ? F1 B1 N1 112.90(19) . . ? N2 B1 N1 108.75(19) . . ? F1 B1 O1 102.22(18) . . ? N2 B1 O1 110.34(18) . . ? N1 B1 O1 109.91(18) . . ? C1 C10 H10A 109.5 . . ? C1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N2 C9 C8 108.4(2) . . ? N2 C9 C14 123.3(2) . . ? C8 C9 C14 128.2(2) . . ? C3 C11 H11A 109.5 . . ? C3 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C3 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C8 C7 C6 106.2(2) . . ? C8 C7 C13 124.1(2) . . ? C6 C7 C13 129.7(2) . . ? _diffrn_measured_fraction_theta_max 0.951 _diffrn_reflns_theta_full 28.43 _diffrn_measured_fraction_theta_full 0.951 _refine_diff_density_max 0.623 _refine_diff_density_min -0.588 _refine_diff_density_rms 0.086 # Attachment 'th.cif' data_th _database_code_depnum_ccdc_archive 'CCDC 689182' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'BODIPY-DMAP-F OTf' _chemical_melting_point ? _chemical_formula_moiety 'C14H17N2-B{C7H10N2}{F} SO3CF3' _chemical_formula_sum 'C22 H27 B F4 N4 O3 S' _chemical_formula_weight 514.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.166(2) _cell_length_b 17.342(3) _cell_length_c 12.365(2) _cell_angle_alpha 90.00 _cell_angle_beta 101.252(4) _cell_angle_gamma 90.00 _cell_volume 2348.4(8) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max .130 _exptl_crystal_size_mid .100 _exptl_crystal_size_min .070 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.455 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1072 _exptl_absorpt_coefficient_mu 0.203 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details none _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10736 _diffrn_reflns_av_R_equivalents 0.0317 _diffrn_reflns_av_sigmaI/netI 0.0395 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 24.00 _reflns_number_total 3684 _reflns_number_gt 2630 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART-97 _computing_cell_refinement SAINT-97 _computing_data_reduction SAINT-97 _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0010P)^2^+9.2000P] 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 3684 _refine_ls_number_parameters 316 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0847 _refine_ls_R_factor_gt 0.0636 _refine_ls_wR_factor_ref 0.1319 _refine_ls_wR_factor_gt 0.1238 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.008 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.73853(9) 0.13460(6) 0.66271(8) 0.0330(3) Uani 1 1 d . . . F1 F 0.2247(2) 0.32769(13) 0.78476(18) 0.0382(6) Uani 1 1 d . . . O1 O 0.8435(2) 0.11637(17) 0.6169(2) 0.0409(7) Uani 1 1 d . . . N3 N 0.3949(3) 0.24537(19) 0.8514(3) 0.0305(8) Uani 1 1 d . . . O2 O 0.6929(3) 0.21194(16) 0.6428(2) 0.0426(8) Uani 1 1 d . . . N4 N 0.5536(3) 0.0892(2) 1.0934(3) 0.0342(8) Uani 1 1 d . . . N2 N 0.4094(3) 0.35792(19) 0.7201(3) 0.0307(8) Uani 1 1 d . . . F2 F 0.5995(3) 0.09681(17) 0.4747(2) 0.0570(8) Uani 1 1 d . . . C17 C 0.5059(4) 0.1420(2) 1.0175(3) 0.0296(9) Uani 1 1 d . . . N1 N 0.2874(3) 0.24391(19) 0.6499(3) 0.0314(8) Uani 1 1 d . . . O3 O 0.7441(3) 0.10651(18) 0.7728(2) 0.0439(8) Uani 1 1 d . . . F3 F 0.6462(3) 0.00203(15) 0.5870(3) 0.0659(9) Uani 1 1 d . . . C5 C 0.4298(3) 0.2992(2) 0.5465(3) 0.0292(9) Uani 1 1 d . . . F4 F 0.5135(2) 0.08522(17) 0.6144(2) 0.0587(8) Uani 1 1 d . . . C15 C 0.3561(4) 0.2396(2) 0.9489(3) 0.0317(9) Uani 1 1 d . . . H15A H 0.2916 0.2706 0.9600 0.038 Uiso 1 1 calc R . . C6 C 0.4659(3) 0.3553(2) 0.6282(3) 0.0297(9) Uani 1 1 d . . . C7 C 0.5438(4) 0.4203(2) 0.6344(3) 0.0326(10) Uani 1 1 d . . . C4 C 0.3383(3) 0.2466(2) 0.5542(3) 0.0296(9) Uani 1 1 d . . . C18 C 0.5501(4) 0.1526(2) 0.9185(3) 0.0309(9) Uani 1 1 d . . . H18A H 0.6182 0.1253 0.9070 0.037 Uiso 1 1 calc R . . C21 C 0.6576(4) 0.0421(3) 1.0789(3) 0.0409(11) Uani 1 1 d . . . H21A H 0.6819 0.0561 1.0112 0.061 Uiso 1 1 calc R . . H21B H 0.6349 -0.0113 1.0763 0.061 Uiso 1 1 calc R . . H21C H 0.7243 0.0506 1.1395 0.061 Uiso 1 1 calc R . . C16 C 0.4074(4) 0.1906(2) 1.0307(3) 0.0321(9) Uani 1 1 d . . . H16A H 0.3778 0.1889 1.0959 0.039 Uiso 1 1 calc R . . C3 C 0.2775(4) 0.1892(2) 0.4801(3) 0.0321(9) Uani 1 1 d . . . C8 C 0.5311(4) 0.4610(2) 0.7284(3) 0.0371(10) Uani 1 1 d . . . H8A H 0.5715 0.5065 0.7531 0.044 Uiso 1 1 calc R . . C1 C 0.2029(4) 0.1865(2) 0.6370(3) 0.0364(10) Uani 1 1 d . . . C2 C 0.1951(4) 0.1539(2) 0.5332(3) 0.0376(10) Uani 1 1 d . . . H2B H 0.1423 0.1144 0.5041 0.045 Uiso 1 1 calc R . . C19 C 0.4934(4) 0.2025(2) 0.8405(3) 0.0321(9) Uani 1 1 d . . . H19A H 0.5237 0.2076 0.7760 0.038 Uiso 1 1 calc R . . C22 C 0.6181(4) 0.0766(3) 0.5804(4) 0.0408(11) Uani 1 1 d . . . C9 C 0.4486(4) 0.4226(2) 0.7793(3) 0.0333(10) Uani 1 1 d . . . C13 C 0.2926(4) 0.1705(3) 0.3653(3) 0.0409(11) Uani 1 1 d . . . H13A H 0.2384 0.1292 0.3365 0.061 Uiso 1 1 calc R . . H13B H 0.3754 0.1551 0.3663 0.061 Uiso 1 1 calc R . . H13C H 0.2736 0.2152 0.3193 0.061 Uiso 1 1 calc R . . C20 C 0.5024(4) 0.0764(3) 1.1923(3) 0.0427(11) Uani 1 1 d . . . H20A H 0.4345 0.1106 1.1915 0.064 Uiso 1 1 calc R . . H20B H 0.5638 0.0864 1.2567 0.064 Uiso 1 1 calc R . . H20C H 0.4752 0.0240 1.1936 0.064 Uiso 1 1 calc R . . C12 C 0.4911(4) 0.2982(3) 0.4483(3) 0.0384(10) Uani 1 1 d . . . H12A H 0.4577 0.2572 0.3995 0.058 Uiso 1 1 calc R . . H12B H 0.5772 0.2902 0.4727 0.058 Uiso 1 1 calc R . . H12C H 0.4775 0.3466 0.4101 0.058 Uiso 1 1 calc R . . C10 C 0.4041(4) 0.4465(3) 0.8800(3) 0.0424(11) Uani 1 1 d . . . H10A H 0.3477 0.4087 0.8970 0.064 Uiso 1 1 calc R . . H10B H 0.3637 0.4955 0.8674 0.064 Uiso 1 1 calc R . . H10C H 0.4720 0.4507 0.9407 0.064 Uiso 1 1 calc R . . C11 C 0.6289(4) 0.4445(3) 0.5608(4) 0.0430(11) Uani 1 1 d . . . H11A H 0.6690 0.4915 0.5880 0.065 Uiso 1 1 calc R . . H11B H 0.5833 0.4524 0.4874 0.065 Uiso 1 1 calc R . . H11C H 0.6888 0.4049 0.5599 0.065 Uiso 1 1 calc R . . B1 B 0.3252(4) 0.2959(3) 0.7510(4) 0.0311(11) Uani 1 1 d . . . C14 C 0.1334(4) 0.1655(3) 0.7235(4) 0.0470(12) Uani 1 1 d . . . H14A H 0.1582 0.1982 0.7866 0.071 Uiso 1 1 calc R . . H14B H 0.1495 0.1127 0.7446 0.071 Uiso 1 1 calc R . . H14C H 0.0477 0.1721 0.6953 0.071 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 S1 0.0317(6) 0.0368(6) 0.0308(5) -0.0014(5) 0.0064(4) 0.0004(5) F1 0.0345(13) 0.0457(15) 0.0364(13) -0.0012(11) 0.0122(10) 0.0064(11) O1 0.0338(16) 0.0522(19) 0.0398(17) 0.0013(14) 0.0149(13) 0.0045(14) N3 0.0313(19) 0.0346(19) 0.0275(18) -0.0007(15) 0.0101(14) -0.0010(15) O2 0.0460(18) 0.0325(17) 0.0473(18) -0.0040(14) 0.0043(14) 0.0003(14) N4 0.0312(19) 0.043(2) 0.0294(18) 0.0023(16) 0.0085(15) 0.0003(16) N2 0.0320(19) 0.033(2) 0.0272(18) 0.0008(15) 0.0057(14) 0.0008(15) F2 0.0591(18) 0.071(2) 0.0359(15) -0.0071(14) -0.0028(13) -0.0043(15) C17 0.031(2) 0.030(2) 0.028(2) -0.0034(18) 0.0047(17) -0.0063(18) N1 0.0301(18) 0.035(2) 0.0296(18) 0.0014(15) 0.0067(15) -0.0025(16) O3 0.0411(17) 0.059(2) 0.0318(17) 0.0015(15) 0.0065(13) 0.0048(15) F3 0.070(2) 0.0337(16) 0.087(2) -0.0082(14) -0.0036(17) -0.0028(14) C5 0.030(2) 0.030(2) 0.027(2) 0.0044(17) 0.0039(17) 0.0058(18) F4 0.0361(15) 0.071(2) 0.0690(19) 0.0020(15) 0.0096(13) -0.0108(14) C15 0.034(2) 0.034(2) 0.029(2) -0.0054(18) 0.0120(18) -0.0006(19) C6 0.026(2) 0.035(2) 0.029(2) 0.0044(18) 0.0055(17) 0.0059(18) C7 0.030(2) 0.030(2) 0.037(2) 0.0062(19) 0.0026(18) 0.0020(18) C4 0.027(2) 0.036(2) 0.027(2) 0.0021(18) 0.0067(17) 0.0024(18) C18 0.027(2) 0.036(2) 0.031(2) -0.0021(18) 0.0093(17) 0.0007(18) C21 0.042(3) 0.042(3) 0.038(2) 0.002(2) 0.004(2) 0.004(2) C16 0.032(2) 0.037(2) 0.029(2) -0.0005(19) 0.0104(18) -0.0039(19) C3 0.034(2) 0.031(2) 0.030(2) -0.0007(18) 0.0031(18) 0.0024(19) C8 0.038(2) 0.030(2) 0.040(3) -0.0026(19) -0.001(2) -0.001(2) C1 0.033(2) 0.040(3) 0.036(2) 0.003(2) 0.0061(19) -0.004(2) C2 0.037(3) 0.036(2) 0.038(2) -0.003(2) 0.004(2) -0.006(2) C19 0.030(2) 0.035(2) 0.033(2) -0.0050(19) 0.0115(18) -0.0032(19) C22 0.040(3) 0.039(3) 0.042(3) 0.001(2) 0.002(2) 0.003(2) C9 0.034(2) 0.032(2) 0.032(2) 0.0018(19) 0.0003(18) 0.0012(19) C13 0.049(3) 0.043(3) 0.031(2) -0.003(2) 0.007(2) -0.002(2) C20 0.042(3) 0.052(3) 0.034(2) 0.004(2) 0.007(2) -0.002(2) C12 0.039(3) 0.042(3) 0.036(2) 0.002(2) 0.012(2) -0.003(2) C10 0.051(3) 0.042(3) 0.032(2) -0.009(2) 0.005(2) 0.000(2) C11 0.033(2) 0.044(3) 0.053(3) 0.007(2) 0.011(2) 0.001(2) B1 0.027(2) 0.035(3) 0.031(3) 0.001(2) 0.005(2) 0.001(2) C14 0.041(3) 0.058(3) 0.045(3) -0.002(2) 0.014(2) -0.013(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 S1 O1 1.433(3) . ? S1 O3 1.436(3) . ? S1 O2 1.439(3) . ? S1 C22 1.822(5) . ? F1 B1 1.385(5) . ? N3 C19 1.355(5) . ? N3 C15 1.362(5) . ? N3 B1 1.593(5) . ? N4 C17 1.344(5) . ? N4 C21 1.460(5) . ? N4 C20 1.465(5) . ? N2 C9 1.363(5) . ? N2 C6 1.405(5) . ? N2 B1 1.525(6) . ? F2 C22 1.331(5) . ? C17 C18 1.418(5) . ? C17 C16 1.420(6) . ? N1 C1 1.359(5) . ? N1 C4 1.411(5) . ? N1 B1 1.533(6) . ? F3 C22 1.329(5) . ? C5 C4 1.387(5) . ? C5 C6 1.403(5) . ? C5 C12 1.507(5) . ? F4 C22 1.325(5) . ? C15 C16 1.359(5) . ? C15 H15A 0.9300 . ? C6 C7 1.418(6) . ? C7 C8 1.391(6) . ? C7 C11 1.497(6) . ? C4 C3 1.430(5) . ? C18 C19 1.357(5) . ? C18 H18A 0.9300 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C16 H16A 0.9300 . ? C3 C2 1.374(6) . ? C3 C13 1.498(5) . ? C8 C9 1.384(6) . ? C8 H8A 0.9300 . ? C1 C2 1.390(6) . ? C1 C14 1.484(6) . ? C2 H2B 0.9300 . ? C19 H19A 0.9300 . ? C9 C10 1.487(6) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 S1 O3 114.40(18) . . ? O1 S1 O2 115.31(19) . . ? O3 S1 O2 115.24(18) . . ? O1 S1 C22 103.2(2) . . ? O3 S1 C22 103.5(2) . . ? O2 S1 C22 102.79(19) . . ? C19 N3 C15 116.8(3) . . ? C19 N3 B1 120.5(3) . . ? C15 N3 B1 122.6(3) . . ? C17 N4 C21 120.7(3) . . ? C17 N4 C20 121.4(3) . . ? C21 N4 C20 117.9(3) . . ? C9 N2 C6 108.3(3) . . ? C9 N2 B1 126.5(3) . . ? C6 N2 B1 125.2(3) . . ? N4 C17 C18 122.3(4) . . ? N4 C17 C16 122.3(4) . . ? C18 C17 C16 115.5(4) . . ? C1 N1 C4 108.0(3) . . ? C1 N1 B1 127.0(3) . . ? C4 N1 B1 125.0(3) . . ? C4 C5 C6 121.3(4) . . ? C4 C5 C12 120.3(4) . . ? C6 C5 C12 118.5(4) . . ? C16 C15 N3 123.0(4) . . ? C16 C15 H15A 118.5 . . ? N3 C15 H15A 118.5 . . ? C5 C6 N2 119.6(4) . . ? C5 C6 C7 132.6(4) . . ? N2 C6 C7 107.3(3) . . ? C8 C7 C6 106.7(4) . . ? C8 C7 C11 123.1(4) . . ? C6 C7 C11 130.2(4) . . ? C5 C4 N1 120.1(3) . . ? C5 C4 C3 132.7(4) . . ? N1 C4 C3 107.2(3) . . ? C19 C18 C17 120.2(4) . . ? C19 C18 H18A 119.9 . . ? C17 C18 H18A 119.9 . . ? N4 C21 H21A 109.5 . . ? N4 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? N4 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C15 C16 C17 120.6(4) . . ? C15 C16 H16A 119.7 . . ? C17 C16 H16A 119.7 . . ? C2 C3 C4 106.4(3) . . ? C2 C3 C13 124.5(4) . . ? C4 C3 C13 129.1(4) . . ? C9 C8 C7 108.7(4) . . ? C9 C8 H8A 125.6 . . ? C7 C8 H8A 125.6 . . ? N1 C1 C2 108.8(4) . . ? N1 C1 C14 122.9(4) . . ? C2 C1 C14 128.3(4) . . ? C3 C2 C1 109.5(4) . . ? C3 C2 H2B 125.3 . . ? C1 C2 H2B 125.3 . . ? N3 C19 C18 123.7(4) . . ? N3 C19 H19A 118.2 . . ? C18 C19 H19A 118.2 . . ? F4 C22 F3 107.6(4) . . ? F4 C22 F2 107.7(4) . . ? F3 C22 F2 107.8(4) . . ? F4 C22 S1 111.1(3) . . ? F3 C22 S1 111.3(3) . . ? F2 C22 S1 111.1(3) . . ? N2 C9 C8 109.0(4) . . ? N2 C9 C10 123.6(4) . . ? C8 C9 C10 127.4(4) . . ? C3 C13 H13A 109.5 . . ? C3 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C3 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N4 C20 H20A 109.5 . . ? N4 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? N4 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C5 C12 H12A 109.5 . . ? C5 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C5 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C7 C11 H11A 109.5 . . ? C7 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C7 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? F1 B1 N2 111.7(4) . . ? F1 B1 N1 111.7(3) . . ? N2 B1 N1 107.2(3) . . ? F1 B1 N3 106.6(3) . . ? N2 B1 N3 110.6(3) . . ? N1 B1 N3 109.1(3) . . ? C1 C14 H14A 109.5 . . ? C1 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C1 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.521 _refine_diff_density_min -0.478 _refine_diff_density_rms 0.078