Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2002 data_pvcu _database_code_CSD 188466 _journal_coden_Cambridge 182 loop_ _publ_author_name 'Pallavicini, Piersandro' 'Amendola, Valeria' 'Massera, Chiara' 'Mundum, Etienne' 'Taglietti, Angelo' _publ_contact_author_name 'Dr Piersandro Pallavicini' _publ_contact_author_address ; Chimica Generale Universitą di Pavia via Taramelli, 12 Pavia 27100 ITALY ; _publ_contact_author_email 'PSP@UNIPV.IT' _publ_requested_journal 'Chemical Communications' _publ_section_title ; "On-off-on" fluorescent indicators of pH windows based on three separated components ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H31 Cl Cu F3 N4 O4.50 S' _chemical_formula_weight 671.61 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' 'Cu' 'Cu' 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'monoclinic' _symmetry_space_group_name_H-M 'C2' 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' _cell_length_a 29.723(5) _cell_length_b 8.506(5) _cell_length_c 11.882(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 94.335(5) _cell_angle_gamma 90.000(5) _cell_volume 2995(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'prismatic' _exptl_crystal_colour 'green' _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.489 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1384 _exptl_absorpt_coefficient_mu 0.948 _exptl_absorpt_correction_type 'semiempirical' _exptl_absorpt_correction_T_min 0.817871 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details sad.abs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'area detector' _diffrn_measurement_method 'omega/2teta scan and profile analysis' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.01 _diffrn_reflns_number 10133 _diffrn_reflns_av_R_equivalents 0.0494 _diffrn_reflns_av_sigmaI/netI 0.1536 _diffrn_reflns_limit_h_min -35 _diffrn_reflns_limit_h_max 37 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.37 _diffrn_reflns_theta_max 27.03 _reflns_number_total 6368 _reflns_number_gt 2777 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.0873P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _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 0.051(18) _refine_ls_number_reflns 6368 _refine_ls_number_parameters 378 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1326 _refine_ls_R_factor_gt 0.0461 _refine_ls_wR_factor_ref 0.1258 _refine_ls_wR_factor_gt 0.0968 _refine_ls_goodness_of_fit_ref 0.584 _refine_ls_restrained_S_all 0.584 _refine_ls_shift/su_max 0.002 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.60874(2) 0.51724(7) 0.32608(5) 0.0531(2) Uani 1 1 d . . . S1 S 0.60696(6) 0.6886(2) -0.12160(18) 0.0811(6) Uani 1 1 d . . . N2 N 0.57160(14) 0.6300(5) 0.2024(4) 0.0497(11) Uani 1 1 d . . . H2 H 0.5907 0.6779 0.1568 0.045(7) Uiso 1 1 calc R . . N3 N 0.59099(16) 0.6987(6) 0.4233(4) 0.0584(13) Uani 1 1 d . . . H3 H 0.5679 0.6665 0.4638 0.045(7) Uiso 1 1 calc R . . N1 N 0.61146(14) 0.3532(5) 0.2006(4) 0.0486(11) Uani 1 1 d . . . N4 N 0.67429(14) 0.6529(5) 0.3562(4) 0.0513(12) Uani 1 1 d . . . F1 F 0.69349(16) 0.6710(7) -0.1092(6) 0.150(2) Uani 1 1 d . . . F2 F 0.6625(2) 0.4588(7) -0.0795(5) 0.147(2) Uani 1 1 d . . . F3 F 0.66321(18) 0.5454(8) -0.2441(4) 0.154(2) Uani 1 1 d . . . O1 O 0.6095(2) 0.7159(7) -0.0051(5) 0.125(2) Uani 1 1 d . . . Cl1 Cl 0.61547(6) 0.3483(2) 0.47472(14) 0.0736(5) Uani 1 1 d . . . O2 O 0.61140(18) 0.8253(7) -0.1856(5) 0.128(2) Uani 1 1 d . . . O3 O 0.57266(17) 0.5826(8) -0.1578(5) 0.132(2) Uani 1 1 d . . . C1 C 0.54426(17) 0.7520(7) 0.2529(5) 0.0546(15) Uani 1 1 d . . . H1 H 0.5195 0.6991 0.2876 0.045(7) Uiso 1 1 calc R . . C2 C 0.52366(19) 0.8721(8) 0.1699(6) 0.0716(18) Uani 1 1 d . . . H2A H 0.5474 0.9185 0.1290 0.084(6) Uiso 1 1 calc R . . H2B H 0.5028 0.8194 0.1156 0.084(6) Uiso 1 1 calc R . . C3 C 0.4993(2) 0.9993(9) 0.2267(6) 0.088(2) Uani 1 1 d . . . H3A H 0.4728 0.9555 0.2580 0.084(6) Uiso 1 1 calc R . . H3B H 0.4892 1.0782 0.1714 0.084(6) Uiso 1 1 calc R . . C4 C 0.5294(2) 1.0760(7) 0.3205(7) 0.084(2) Uani 1 1 d . . . H4A H 0.5536 1.1323 0.2878 0.084(6) Uiso 1 1 calc R . . H4B H 0.5118 1.1516 0.3599 0.084(6) Uiso 1 1 calc R . . C5 C 0.5489(2) 0.9579(7) 0.4023(6) 0.077(2) Uani 1 1 d . . . H5A H 0.5249 0.9122 0.4425 0.084(6) Uiso 1 1 calc R . . H5B H 0.5696 1.0103 0.4572 0.084(6) Uiso 1 1 calc R . . C6 C 0.57404(18) 0.8267(7) 0.3460(5) 0.0558(15) Uani 1 1 d . . . H6 H 0.6000 0.8734 0.3124 0.045(7) Uiso 1 1 calc R . . C7 C 0.54663(16) 0.5089(9) 0.1372(5) 0.0628(14) Uani 1 1 d . . . H7A H 0.5354 0.5510 0.0645 0.084(6) Uiso 1 1 calc R . . H7B H 0.5210 0.4748 0.1768 0.084(6) Uiso 1 1 calc R . . C8 C 0.57754(18) 0.3713(7) 0.1205(5) 0.0506(14) Uani 1 1 d . . . C9 C 0.5720(2) 0.2709(8) 0.0296(5) 0.0641(17) Uani 1 1 d . . . H9 H 0.5482 0.2868 -0.0247 0.067(5) Uiso 1 1 calc R . . C10 C 0.6006(2) 0.1501(8) 0.0180(5) 0.0642(16) Uani 1 1 d . . . H10 H 0.5962 0.0816 -0.0428 0.067(5) Uiso 1 1 calc R . . C11 C 0.63733(18) 0.1284(7) 0.0992(5) 0.0547(14) Uani 1 1 d . . . C12 C 0.64212(18) 0.2333(6) 0.1904(5) 0.0498(14) Uani 1 1 d . . . C13 C 0.67858(19) 0.2157(7) 0.2717(5) 0.0597(15) Uani 1 1 d . . . H13 H 0.6818 0.2832 0.3334 0.067(5) Uiso 1 1 calc R . . C14 C 0.7091(2) 0.0989(7) 0.2593(6) 0.0693(17) Uani 1 1 d . . . H14 H 0.7331 0.0877 0.3135 0.067(5) Uiso 1 1 calc R . . C15 C 0.7054(2) -0.0031(9) 0.1693(6) 0.0708(17) Uani 1 1 d . . . H15 H 0.7272 -0.0805 0.1626 0.067(5) Uiso 1 1 calc R . . C16 C 0.67051(19) 0.0090(9) 0.0909(5) 0.0685(15) Uani 1 1 d . . . H16 H 0.6680 -0.0611 0.0307 0.067(5) Uiso 1 1 calc R . . C17 C 0.6284(2) 0.7443(9) 0.5021(5) 0.077(2) Uani 1 1 d . . . H17A H 0.6290 0.6770 0.5681 0.084(6) Uiso 1 1 calc R . . H17B H 0.6239 0.8515 0.5267 0.084(6) Uiso 1 1 calc R . . C18 C 0.67324(19) 0.7332(6) 0.4509(5) 0.0556(15) Uani 1 1 d . . . C19 C 0.7121(2) 0.8049(7) 0.5037(5) 0.0704(18) Uani 1 1 d . . . H19 H 0.7101 0.8634 0.5693 0.067(5) Uiso 1 1 calc R . . C20 C 0.7522(2) 0.7883(8) 0.4586(5) 0.0729(19) Uani 1 1 d . . . H20 H 0.7780 0.8326 0.4948 0.067(5) Uiso 1 1 calc R . . C21 C 0.7552(2) 0.7054(7) 0.3586(5) 0.0636(16) Uani 1 1 d . . . C22 C 0.71455(18) 0.6414(6) 0.3070(5) 0.0531(14) Uani 1 1 d . . . C23 C 0.71576(19) 0.5664(6) 0.2035(5) 0.0608(17) Uani 1 1 d . . . H23 H 0.6892 0.5279 0.1669 0.067(5) Uiso 1 1 calc R . . C24 C 0.7555(2) 0.5490(8) 0.1552(6) 0.082(2) Uani 1 1 d . . . H24 H 0.7559 0.4980 0.0861 0.067(5) Uiso 1 1 calc R . . C25 C 0.7953(2) 0.6061(10) 0.2076(7) 0.087(2) Uani 1 1 d . . . H25 H 0.8224 0.5893 0.1750 0.067(5) Uiso 1 1 calc R . . C26 C 0.7953(2) 0.6854(9) 0.3050(6) 0.079(2) Uani 1 1 d . . . H26 H 0.8221 0.7276 0.3374 0.067(5) Uiso 1 1 calc R . . C27 C 0.6579(3) 0.5838(11) -0.1408(8) 0.091(2) Uani 1 1 d . . . O1S O 0.5442(2) 0.4030(11) 0.6630(7) 0.183(3) Uani 1 1 d . . . O2S O 0.5000 0.5802(10) 0.5000 0.153(4) Uani 1 2 d S . . 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 0.0546(3) 0.0552(4) 0.0489(4) -0.0035(4) -0.0005(3) 0.0024(4) S1 0.0794(12) 0.0764(13) 0.0895(14) -0.0109(11) 0.0185(11) 0.0063(10) N2 0.042(2) 0.058(3) 0.049(3) -0.001(2) 0.006(2) -0.003(2) N3 0.060(3) 0.064(3) 0.052(3) -0.007(3) 0.011(3) 0.002(3) N1 0.047(2) 0.048(3) 0.051(3) 0.000(2) 0.003(2) -0.006(2) N4 0.051(3) 0.054(3) 0.048(3) -0.009(2) -0.002(2) -0.001(2) F1 0.076(3) 0.158(5) 0.218(6) -0.004(5) 0.020(4) 0.007(3) F2 0.149(5) 0.111(4) 0.183(5) 0.044(4) 0.017(4) 0.039(3) F3 0.172(4) 0.205(6) 0.089(3) -0.020(4) 0.031(3) 0.087(5) O1 0.153(5) 0.131(5) 0.099(4) -0.044(4) 0.069(4) -0.037(4) Cl1 0.0873(12) 0.0755(11) 0.0577(10) 0.0107(9) 0.0036(9) 0.0079(10) O2 0.125(4) 0.110(5) 0.152(5) 0.038(4) 0.041(4) 0.047(4) O3 0.085(3) 0.158(7) 0.151(5) -0.055(4) -0.016(3) -0.003(4) C1 0.041(3) 0.059(4) 0.066(4) 0.005(3) 0.014(3) -0.004(3) C2 0.056(4) 0.070(4) 0.087(5) 0.014(4) -0.007(3) 0.004(3) C3 0.069(4) 0.065(4) 0.130(6) 0.009(5) 0.010(4) 0.016(4) C4 0.075(4) 0.053(4) 0.124(7) -0.012(4) 0.009(5) 0.006(3) C5 0.073(4) 0.068(5) 0.092(5) -0.003(4) 0.028(4) 0.006(3) C6 0.044(3) 0.058(4) 0.067(4) 0.003(3) 0.016(3) 0.003(3) C7 0.046(3) 0.073(4) 0.067(3) -0.013(4) -0.005(3) 0.008(4) C8 0.047(3) 0.057(4) 0.047(3) 0.000(3) -0.001(3) -0.009(3) C9 0.057(4) 0.074(4) 0.059(4) -0.012(3) -0.007(3) -0.010(3) C10 0.069(4) 0.067(4) 0.056(4) -0.007(3) 0.004(3) -0.009(4) C11 0.060(4) 0.053(4) 0.052(4) 0.000(3) 0.007(3) -0.014(3) C12 0.057(3) 0.044(3) 0.050(3) 0.004(3) 0.009(3) -0.005(3) C13 0.062(4) 0.055(4) 0.060(4) -0.004(3) -0.009(3) 0.000(3) C14 0.074(4) 0.053(4) 0.079(5) 0.008(4) -0.005(4) 0.004(4) C15 0.073(4) 0.058(4) 0.082(4) 0.004(4) 0.010(4) 0.005(4) C16 0.073(4) 0.047(3) 0.087(4) -0.014(5) 0.021(3) -0.005(4) C17 0.087(5) 0.089(5) 0.054(4) -0.016(4) -0.004(4) 0.008(4) C18 0.068(4) 0.048(3) 0.049(4) -0.002(3) -0.008(3) -0.002(3) C19 0.105(5) 0.056(4) 0.047(4) -0.005(3) -0.023(4) -0.005(4) C20 0.069(4) 0.082(5) 0.063(5) 0.000(4) -0.024(4) -0.012(4) C21 0.061(4) 0.056(4) 0.071(4) 0.015(3) -0.010(4) -0.005(3) C22 0.052(3) 0.052(3) 0.055(4) 0.001(3) -0.001(3) -0.005(3) C23 0.050(3) 0.067(5) 0.065(4) -0.005(3) 0.004(3) -0.011(3) C24 0.078(4) 0.077(6) 0.093(5) -0.007(4) 0.020(4) -0.016(4) C25 0.060(4) 0.112(6) 0.092(6) 0.005(5) 0.015(4) -0.009(4) C26 0.049(4) 0.094(5) 0.091(5) 0.011(5) -0.012(4) -0.016(4) C27 0.090(6) 0.096(6) 0.091(6) 0.009(5) 0.026(5) 0.005(5) O1S 0.119(5) 0.242(9) 0.191(7) -0.099(7) 0.030(5) -0.034(5) O2S 0.171(8) 0.106(7) 0.198(9) 0.000 0.122(7) 0.000 _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 N2 2.013(4) . ? Cu1 N3 2.022(5) . ? Cu1 N1 2.048(5) . ? Cu1 N4 2.269(4) . ? Cu1 Cl1 2.2743(19) . ? S1 O2 1.401(6) . ? S1 O3 1.404(5) . ? S1 O1 1.401(5) . ? S1 C27 1.787(8) . ? N2 C7 1.458(7) . ? N2 C1 1.473(7) . ? N3 C17 1.452(7) . ? N3 C6 1.488(7) . ? N1 C8 1.342(6) . ? N1 C12 1.379(7) . ? N4 C18 1.319(6) . ? N4 C22 1.374(6) . ? F1 C27 1.323(9) . ? F2 C27 1.290(8) . ? F3 C27 1.291(9) . ? C1 C6 1.505(8) . ? C1 C2 1.516(8) . ? C2 C3 1.492(9) . ? C3 C4 1.523(9) . ? C4 C5 1.486(8) . ? C5 C6 1.524(8) . ? C7 C8 1.511(8) . ? C8 C9 1.377(8) . ? C9 C10 1.347(8) . ? C10 C11 1.413(7) . ? C11 C12 1.402(7) . ? C11 C16 1.424(8) . ? C12 C13 1.404(7) . ? C13 C14 1.360(8) . ? C14 C15 1.375(9) . ? C15 C16 1.346(8) . ? C17 C18 1.508(8) . ? C18 C19 1.410(8) . ? C19 C20 1.352(9) . ? C20 C21 1.390(8) . ? C21 C26 1.402(9) . ? C21 C22 1.421(8) . ? C22 C23 1.389(7) . ? C23 C24 1.360(8) . ? C24 C25 1.383(9) . ? C25 C26 1.339(9) . ? 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 N2 Cu1 N3 84.32(19) . . ? N2 Cu1 N1 80.97(18) . . ? N3 Cu1 N1 164.26(18) . . ? N2 Cu1 N4 106.86(17) . . ? N3 Cu1 N4 77.28(17) . . ? N1 Cu1 N4 112.38(16) . . ? N2 Cu1 Cl1 151.54(13) . . ? N3 Cu1 Cl1 92.87(15) . . ? N1 Cu1 Cl1 97.39(14) . . ? N4 Cu1 Cl1 100.06(12) . . ? O2 S1 O3 117.6(4) . . ? O2 S1 O1 113.5(4) . . ? O3 S1 O1 113.1(4) . . ? O2 S1 C27 103.2(4) . . ? O3 S1 C27 104.1(4) . . ? O1 S1 C27 103.1(4) . . ? C7 N2 C1 116.1(4) . . ? C7 N2 Cu1 106.3(4) . . ? C1 N2 Cu1 109.1(3) . . ? C17 N3 C6 114.2(5) . . ? C17 N3 Cu1 110.6(4) . . ? C6 N3 Cu1 107.3(3) . . ? C8 N1 C12 119.2(5) . . ? C8 N1 Cu1 111.7(4) . . ? C12 N1 Cu1 129.1(4) . . ? C18 N4 C22 118.5(5) . . ? C18 N4 Cu1 108.8(3) . . ? C22 N4 Cu1 131.4(3) . . ? N2 C1 C6 106.6(4) . . ? N2 C1 C2 114.7(5) . . ? C6 C1 C2 112.3(5) . . ? C3 C2 C1 112.4(6) . . ? C2 C3 C4 111.3(5) . . ? C5 C4 C3 111.6(6) . . ? C4 C5 C6 112.9(5) . . ? N3 C6 C1 107.3(5) . . ? N3 C6 C5 114.8(5) . . ? C1 C6 C5 110.6(5) . . ? N2 C7 C8 109.1(4) . . ? N1 C8 C9 121.6(6) . . ? N1 C8 C7 115.3(5) . . ? C9 C8 C7 123.1(5) . . ? C10 C9 C8 120.9(6) . . ? C9 C10 C11 119.4(6) . . ? C12 C11 C10 118.2(5) . . ? C12 C11 C16 118.5(5) . . ? C10 C11 C16 123.3(5) . . ? N1 C12 C11 120.6(5) . . ? N1 C12 C13 120.0(5) . . ? C11 C12 C13 119.4(5) . . ? C14 C13 C12 119.3(6) . . ? C13 C14 C15 122.1(6) . . ? C16 C15 C14 120.1(7) . . ? C15 C16 C11 120.5(6) . . ? N3 C17 C18 112.4(5) . . ? N4 C18 C19 122.1(6) . . ? N4 C18 C17 117.1(5) . . ? C19 C18 C17 120.8(5) . . ? C20 C19 C18 119.8(6) . . ? C19 C20 C21 120.5(6) . . ? C20 C21 C26 124.1(6) . . ? C20 C21 C22 117.1(6) . . ? C26 C21 C22 118.8(6) . . ? N4 C22 C23 119.4(5) . . ? N4 C22 C21 121.9(5) . . ? C23 C22 C21 118.7(5) . . ? C24 C23 C22 120.3(5) . . ? C23 C24 C25 120.9(7) . . ? C26 C25 C24 120.6(7) . . ? C25 C26 C21 120.7(6) . . ? F3 C27 F2 108.2(8) . . ? F3 C27 F1 105.0(7) . . ? F2 C27 F1 104.7(8) . . ? F3 C27 S1 114.4(7) . . ? F2 C27 S1 113.2(6) . . ? F1 C27 S1 110.5(6) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.03 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.302 _refine_diff_density_min -0.186 _refine_diff_density_rms 0.048