Supplementary Material (ESI) for Perkin Transactions This journal is © The Royal Society of Chemistry 2001 data_prm98m _database_code_CSD 159689 _journal_coden_Cambridge 188 _publ_section_title ; Optical-structural correlation in a novel quinoxaline-based anion sensor ; _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _pbl_requested_journal ' Perkin Trans II ' _publ_contact_author_name ' Paul E. Kruger ' _publ_contact_author_address ; Department of Chemistry Trinity College Dublin Dublin 2 Ireland ; _publ_contact_author_phone ' 353 1 608 1422 ' _publ_contact_author_fax ' 353 1 671 2826 ' _publ_contact_author_email ' paul.kruger@tcd.ie ' loop_ _publ_author_name _publ_author_address ' Paul E. Kruger ' ; Department of Chemistry Trinity College Dublin Dublin 2 Ireland ; ' Philip R. Mackie ' ; Department of Chemistry Trinity College Dublin Dublin 2 Ireland ; ' Mark Nieuwenhuyzen' ; Chemistry Department Queen's University Belfast, BT9 5AG UK ; _publ_section_title ; 'Optical-structural correlation in a novel quinoxaline-based anion sensor ' ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H13 F6 N4 P' _chemical_formula_weight 430.29 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' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'P' 'P' 0.1023 0.0942 '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 9.0090(12) _cell_length_b 20.526(3) _cell_length_c 9.6235(13) _cell_angle_alpha 90.00 _cell_angle_beta 92.156(3) _cell_angle_gamma 90.00 _cell_volume 1778.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas Not_measured _exptl_crystal_density_diffrn 1.607 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 872 _exptl_absorpt_coefficient_mu 0.228 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9432 _exptl_absorpt_correction_T_max 0.9516 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 18549 _diffrn_reflns_av_R_equivalents 0.1000 _diffrn_reflns_av_sigmaI/netI 0.0919 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 28.65 _reflns_number_total 4153 _reflns_number_gt 2223 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0604P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'Difference map' _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4153 _refine_ls_number_parameters 314 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1090 _refine_ls_R_factor_gt 0.0526 _refine_ls_wR_factor_ref 0.1317 _refine_ls_wR_factor_gt 0.1096 _refine_ls_goodness_of_fit_ref 0.921 _refine_ls_restrained_S_all 0.921 _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 P1 P 0.43566(8) 0.65668(4) 0.72133(7) 0.0304(2) Uani 1 1 d . . . F11 F 0.55966(19) 0.62260(9) 0.63177(17) 0.0509(5) Uani 1 1 d . . . F12 F 0.37821(19) 0.69731(9) 0.58858(17) 0.0508(5) Uani 1 1 d . . . F13 F 0.32184(19) 0.59953(9) 0.68129(17) 0.0499(5) Uani 1 1 d . . . F14 F 0.49231(17) 0.61612(8) 0.85479(16) 0.0390(4) Uani 1 1 d . . . F15 F 0.31157(17) 0.69076(8) 0.81189(17) 0.0437(5) Uani 1 1 d . . . F16 F 0.54929(17) 0.71368(8) 0.76258(17) 0.0400(4) Uani 1 1 d . . . N1 N 0.2892(3) 0.63576(11) 1.1341(2) 0.0295(5) Uani 1 1 d . . . H1 H 0.210(4) 0.6727(17) 1.104(3) 0.076(11) Uiso 1 1 d . . . C2 C 0.3894(3) 0.64798(15) 1.2382(3) 0.0328(7) Uani 1 1 d . . . H2 H 0.386(3) 0.6908(14) 1.270(3) 0.032(8) Uiso 1 1 d . . . C3 C 0.4851(3) 0.60058(15) 1.2852(3) 0.0351(7) Uani 1 1 d . . . H3 H 0.555(3) 0.6104(13) 1.358(3) 0.034(8) Uiso 1 1 d . . . C4 C 0.4762(3) 0.53993(15) 1.2247(3) 0.0334(7) Uani 1 1 d . . . H4 H 0.543(3) 0.5052(12) 1.250(2) 0.026(7) Uiso 1 1 d . . . C5 C 0.3708(3) 0.52764(14) 1.1199(3) 0.0286(6) Uani 1 1 d . . . H5 H 0.366(3) 0.4846(15) 1.076(3) 0.046(9) Uiso 1 1 d . . . C6 C 0.2752(3) 0.57688(13) 1.0753(3) 0.0257(6) Uani 1 1 d . . . C7 C 0.1581(3) 0.56466(13) 0.9632(3) 0.0247(6) Uani 1 1 d . . . N8 N 0.1796(2) 0.50795(11) 0.9016(2) 0.0287(5) Uani 1 1 d . . . C9 C 0.0844(3) 0.48801(13) 0.7972(3) 0.0289(6) Uani 1 1 d . . . C10 C 0.1021(4) 0.42620(14) 0.7360(3) 0.0342(7) Uani 1 1 d . . . H10 H 0.189(3) 0.4020(13) 0.768(3) 0.036(8) Uiso 1 1 d . . . C11 C 0.0018(4) 0.40592(16) 0.6349(3) 0.0411(8) Uani 1 1 d . . . H11 H 0.013(3) 0.3638(15) 0.596(3) 0.049(9) Uiso 1 1 d . . . C12 C -0.1163(4) 0.44673(16) 0.5880(3) 0.0378(7) Uani 1 1 d . . . H12 H -0.181(3) 0.4310(15) 0.519(3) 0.053(10) Uiso 1 1 d . . . C13 C -0.1349(3) 0.50731(16) 0.6439(3) 0.0343(7) Uani 1 1 d . . . H13 H -0.216(3) 0.5378(14) 0.616(3) 0.042(9) Uiso 1 1 d . . . C14 C -0.0337(3) 0.52864(13) 0.7512(3) 0.0289(6) Uani 1 1 d . . . N15 N -0.0568(2) 0.58654(11) 0.8151(2) 0.0293(5) Uani 1 1 d . . . C16 C 0.0311(3) 0.60504(13) 0.9203(3) 0.0252(6) Uani 1 1 d . . . C17 C -0.0262(3) 0.66601(12) 0.9863(3) 0.0258(6) Uani 1 1 d . . . C18 C -0.1774(3) 0.68052(14) 0.9693(3) 0.0318(7) Uani 1 1 d . . . H18 H -0.244(3) 0.6503(13) 0.919(3) 0.036(8) Uiso 1 1 d . . . C19 C -0.2308(3) 0.73615(15) 1.0312(3) 0.0343(7) Uani 1 1 d . . . H19 H -0.334(3) 0.7458(13) 1.019(3) 0.041(8) Uiso 1 1 d . . . C20 C -0.1358(3) 0.77597(15) 1.1068(3) 0.0353(7) Uani 1 1 d . . . H20 H -0.166(3) 0.8130(13) 1.150(3) 0.033(8) Uiso 1 1 d . . . C21 C 0.0111(3) 0.75893(14) 1.1200(3) 0.0329(7) Uani 1 1 d . . . H21 H 0.082(3) 0.7829(13) 1.172(3) 0.035(8) Uiso 1 1 d . . . N22 N 0.0651(2) 0.70527(11) 1.0598(2) 0.0296(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 P1 0.0274(4) 0.0330(4) 0.0305(4) 0.0037(3) -0.0020(3) -0.0007(3) F11 0.0506(12) 0.0573(12) 0.0457(10) -0.0069(9) 0.0130(9) 0.0098(10) F12 0.0533(12) 0.0597(12) 0.0385(10) 0.0194(9) -0.0105(8) 0.0015(10) F13 0.0507(11) 0.0488(11) 0.0488(11) 0.0004(9) -0.0138(9) -0.0185(9) F14 0.0393(10) 0.0414(10) 0.0357(9) 0.0097(8) -0.0061(7) 0.0015(8) F15 0.0312(10) 0.0522(11) 0.0480(10) 0.0017(9) 0.0062(8) 0.0061(8) F16 0.0308(10) 0.0379(10) 0.0509(10) 0.0035(8) -0.0032(8) -0.0060(8) N1 0.0253(13) 0.0290(13) 0.0336(13) 0.0005(10) -0.0041(10) -0.0009(11) C2 0.0289(16) 0.0304(17) 0.0384(16) -0.0034(13) -0.0062(13) -0.0021(13) C3 0.0280(16) 0.0399(18) 0.0369(17) 0.0004(14) -0.0061(14) -0.0018(14) C4 0.0303(17) 0.0342(17) 0.0355(16) 0.0036(13) -0.0008(13) 0.0025(14) C5 0.0260(15) 0.0303(16) 0.0297(15) 0.0009(12) 0.0019(12) 0.0008(12) C6 0.0210(14) 0.0302(15) 0.0263(14) -0.0001(11) 0.0044(11) -0.0004(11) C7 0.0242(14) 0.0282(14) 0.0218(13) 0.0034(11) 0.0028(11) -0.0025(12) N8 0.0290(13) 0.0295(13) 0.0276(12) -0.0004(10) 0.0019(10) -0.0044(10) C9 0.0298(16) 0.0310(15) 0.0261(14) 0.0013(12) 0.0028(12) -0.0052(13) C10 0.0389(18) 0.0346(17) 0.0294(16) -0.0024(13) 0.0041(14) -0.0029(14) C11 0.054(2) 0.0375(18) 0.0319(16) -0.0088(14) 0.0085(15) -0.0132(17) C12 0.0399(19) 0.048(2) 0.0259(15) -0.0046(14) 0.0020(14) -0.0128(16) C13 0.0341(17) 0.0444(19) 0.0244(14) -0.0002(13) 0.0021(13) -0.0081(15) C14 0.0279(16) 0.0343(16) 0.0247(14) 0.0010(12) 0.0027(12) -0.0066(13) N15 0.0271(13) 0.0355(13) 0.0254(12) 0.0015(10) 0.0009(10) -0.0051(11) C16 0.0236(14) 0.0281(14) 0.0240(13) 0.0023(11) 0.0019(11) -0.0042(12) C17 0.0268(15) 0.0292(15) 0.0211(13) 0.0017(11) -0.0021(11) 0.0017(12) C18 0.0264(16) 0.0390(17) 0.0299(15) -0.0018(13) -0.0027(12) 0.0012(14) C19 0.0255(17) 0.0444(18) 0.0326(16) -0.0037(13) -0.0007(13) 0.0049(14) C20 0.0355(18) 0.0336(17) 0.0366(17) -0.0027(14) -0.0011(14) 0.0046(14) C21 0.0340(18) 0.0308(16) 0.0335(16) -0.0014(13) -0.0039(13) -0.0003(14) N22 0.0279(13) 0.0268(12) 0.0338(13) -0.0010(10) -0.0031(10) 0.0013(10) _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 P1 F16 1.5949(17) . ? P1 F12 1.5956(17) . ? P1 F13 1.5958(18) . ? P1 F11 1.5976(17) . ? P1 F14 1.5981(16) . ? P1 F15 1.6037(17) . ? N1 C6 1.339(3) . ? N1 C2 1.346(3) . ? C2 C3 1.366(4) . ? C3 C4 1.375(4) . ? C4 C5 1.383(4) . ? C5 C6 1.386(4) . ? C6 C7 1.501(4) . ? C7 N8 1.324(3) . ? C7 C16 1.460(4) . ? N8 C9 1.359(3) . ? C9 C14 1.410(4) . ? C9 C10 1.410(4) . ? C10 C11 1.368(4) . ? C11 C12 1.414(5) . ? C12 C13 1.368(4) . ? C13 C14 1.420(4) . ? C14 N15 1.358(3) . ? N15 C16 1.317(3) . ? C16 C17 1.503(4) . ? C17 N22 1.335(3) . ? C17 C18 1.398(4) . ? C18 C19 1.383(4) . ? C19 C20 1.372(4) . ? C20 C21 1.370(4) . ? C21 N22 1.344(3) . ? 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 F16 P1 F12 90.10(9) . . ? F16 P1 F13 179.56(10) . . ? F12 P1 F13 90.27(10) . . ? F16 P1 F11 90.01(10) . . ? F12 P1 F11 90.53(10) . . ? F13 P1 F11 90.22(10) . . ? F16 P1 F14 89.98(9) . . ? F12 P1 F14 179.65(11) . . ? F13 P1 F14 89.65(9) . . ? F11 P1 F14 89.82(9) . . ? F16 P1 F15 89.93(9) . . ? F12 P1 F15 89.73(10) . . ? F13 P1 F15 89.84(10) . . ? F11 P1 F15 179.73(11) . . ? F14 P1 F15 89.92(9) . . ? C6 N1 C2 122.2(2) . . ? N1 C2 C3 120.7(3) . . ? C2 C3 C4 118.6(3) . . ? C3 C4 C5 120.1(3) . . ? C4 C5 C6 119.7(3) . . ? N1 C6 C5 118.7(2) . . ? N1 C6 C7 120.5(2) . . ? C5 C6 C7 120.9(2) . . ? N8 C7 C16 119.9(2) . . ? N8 C7 C6 111.0(2) . . ? C16 C7 C6 129.1(2) . . ? C7 N8 C9 119.8(2) . . ? N8 C9 C14 120.1(2) . . ? N8 C9 C10 120.1(3) . . ? C14 C9 C10 119.8(3) . . ? C11 C10 C9 119.3(3) . . ? C10 C11 C12 121.0(3) . . ? C13 C12 C11 121.0(3) . . ? C12 C13 C14 118.8(3) . . ? N15 C14 C9 120.1(2) . . ? N15 C14 C13 119.6(3) . . ? C9 C14 C13 120.1(3) . . ? C16 N15 C14 120.2(2) . . ? N15 C16 C7 119.7(2) . . ? N15 C16 C17 111.0(2) . . ? C7 C16 C17 129.1(2) . . ? N22 C17 C18 120.8(2) . . ? N22 C17 C16 120.8(2) . . ? C18 C17 C16 118.5(2) . . ? C19 C18 C17 118.6(3) . . ? C20 C19 C18 120.0(3) . . ? C21 C20 C19 118.6(3) . . ? N22 C21 C20 122.2(3) . . ? C17 N22 C21 119.8(2) . . ? _diffrn_measured_fraction_theta_max 0.910 _diffrn_reflns_theta_full 28.65 _diffrn_measured_fraction_theta_full 0.910 _refine_diff_density_max 0.294 _refine_diff_density_min -0.500 _refine_diff_density_rms 0.078