# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics # This journal is © The Owner Societies 2012 data_global _journal_name_full Phys.Chem.Chem.Phys.(PCCP) _journal_coden_Cambridge 1326 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Pi-Tai Chou' _publ_contact_author_email chop@ntu.edu.tw _publ_section_title ; Structural Tuning Intra- versus Inter-Molecular Proton Transfer Reaction in the Excited State. ; loop_ _publ_author_name 'Min-Wen Chung' 'Jia-Ling Liao' 'Kuo-Chun Tang' 'Cheng-Chih Hsieh' 'Tsung-Yi Lin' 'Chun Liu' 'Gene-Hsiang Lee' 'Yun Chi' 'Pi-Tai Chou' data_2 _database_code_depnum_ccdc_archive 'CCDC 857564' #TrackingRef '- cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H10 F3 N3' _chemical_formula_weight 253.23 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' _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 11.5553(3) _cell_length_b 8.1262(2) _cell_length_c 13.2771(3) _cell_angle_alpha 90.00 _cell_angle_beta 113.9783(15) _cell_angle_gamma 90.00 _cell_volume 1139.14(5) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 7436 _cell_measurement_theta_min 1.98 _cell_measurement_theta_max 27.50 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.477 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.126 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.906 _exptl_absorpt_correction_T_max 0.984 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 'NONIUS KappaCCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7436 _diffrn_reflns_av_R_equivalents 0.0429 _diffrn_reflns_av_sigmaI/netI 0.0396 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2600 _reflns_number_gt 1814 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'NONIUS COLLECT' _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _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^)+(0.1063P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2600 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0773 _refine_ls_R_factor_gt 0.0557 _refine_ls_wR_factor_ref 0.1693 _refine_ls_wR_factor_gt 0.1556 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.091 _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 N1 N 0.55639(12) 0.13032(19) 0.17688(10) 0.0520(4) Uani 1 1 d . . . N2 N 0.58483(12) 0.33567(16) 0.03438(10) 0.0465(4) Uani 1 1 d . . . H2 H 0.5312 0.3607 0.0638 0.056 Uiso 1 1 calc R . . N3 N 0.61221(13) 0.43696(17) -0.03140(12) 0.0527(4) Uani 1 1 d . . . C1 C 0.52655(16) 0.0279(3) 0.24140(13) 0.0623(5) Uani 1 1 d . . . H1 H 0.4797 0.0699 0.2802 0.075 Uiso 1 1 calc R . . C2 C 0.56065(17) -0.1358(3) 0.25419(15) 0.0685(6) Uani 1 1 d . . . H2A H 0.5378 -0.2051 0.3008 0.082 Uiso 1 1 calc R . . C3 C 0.62826(15) -0.1966(3) 0.19818(13) 0.0637(5) Uani 1 1 d . . . H3 H 0.6525 -0.3092 0.2063 0.076 Uiso 1 1 calc R . . C4 C 0.66182(14) -0.0963(2) 0.12973(12) 0.0495(4) Uani 1 1 d . . . C5 C 0.62272(13) 0.06815(19) 0.12235(11) 0.0429(4) Uani 1 1 d . . . C6 C 0.73235(16) -0.1646(2) 0.06659(15) 0.0584(5) Uani 1 1 d . . . H6A H 0.6727 -0.1747 -0.0117 0.070 Uiso 1 1 calc R . . H6B H 0.7614 -0.2769 0.0943 0.070 Uiso 1 1 calc R . . C7 C 0.84705(16) -0.0645(2) 0.07231(15) 0.0619(5) Uani 1 1 d . . . H7A H 0.8883 -0.0152 0.1467 0.074 Uiso 1 1 calc R . . H7B H 0.9088 -0.1399 0.0623 0.074 Uiso 1 1 calc R . . C8 C 0.81523(16) 0.0716(2) -0.01282(16) 0.0601(5) Uani 1 1 d . . . H8A H 0.8946 0.1284 -0.0039 0.072 Uiso 1 1 calc R . . H8B H 0.7797 0.0213 -0.0871 0.072 Uiso 1 1 calc R . . C9 C 0.72297(13) 0.1975(2) -0.00667(12) 0.0460(4) Uani 1 1 d . . . C10 C 0.64714(12) 0.19048(18) 0.05194(11) 0.0413(4) Uani 1 1 d . . . C11 C 0.69602(15) 0.3531(2) -0.05637(13) 0.0496(4) Uani 1 1 d . A . C12 C 0.7494(2) 0.4307(3) -0.12837(18) 0.0674(5) Uani 1 1 d . . . F1 F 0.6852(3) 0.5655(3) -0.1802(2) 0.1256(9) Uani 0.856(3) 1 d P A 1 F2 F 0.86677(19) 0.4813(4) -0.07499(17) 0.1319(10) Uani 0.856(3) 1 d P A 1 F3 F 0.7491(3) 0.3341(3) -0.20791(16) 0.1135(8) Uani 0.856(3) 1 d P A 1 F1' F 0.778(2) 0.5693(18) -0.1112(16) 0.1256(9) Uani 0.144(3) 1 d P A 2 F2' F 0.8604(12) 0.362(2) -0.1148(12) 0.1319(10) Uani 0.144(3) 1 d P A 2 F3' F 0.6907(17) 0.4189(18) -0.2205(12) 0.1135(8) Uani 0.144(3) 1 d P 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 N1 0.0452(7) 0.0666(10) 0.0485(7) 0.0005(6) 0.0236(6) -0.0039(6) N2 0.0509(7) 0.0420(8) 0.0574(7) -0.0019(6) 0.0329(6) -0.0008(5) N3 0.0637(9) 0.0408(8) 0.0676(8) 0.0005(6) 0.0410(7) -0.0037(6) C1 0.0508(9) 0.0880(15) 0.0499(9) 0.0096(9) 0.0223(7) -0.0077(9) C2 0.0537(10) 0.0877(16) 0.0562(10) 0.0281(10) 0.0142(8) -0.0059(9) C3 0.0513(9) 0.0635(12) 0.0598(10) 0.0209(8) 0.0056(8) 0.0008(8) C4 0.0382(8) 0.0528(10) 0.0459(8) 0.0046(7) 0.0051(6) -0.0002(7) C5 0.0354(7) 0.0497(9) 0.0393(7) -0.0007(6) 0.0109(6) -0.0044(6) C6 0.0539(9) 0.0490(10) 0.0638(10) 0.0000(8) 0.0152(8) 0.0085(8) C7 0.0457(9) 0.0623(12) 0.0739(11) -0.0057(9) 0.0204(8) 0.0130(8) C8 0.0539(10) 0.0622(12) 0.0751(11) -0.0095(9) 0.0374(9) 0.0045(8) C9 0.0437(8) 0.0506(10) 0.0488(8) -0.0099(7) 0.0241(6) -0.0040(7) C10 0.0379(7) 0.0423(8) 0.0437(7) -0.0068(6) 0.0166(6) -0.0038(6) C11 0.0531(9) 0.0475(10) 0.0579(9) -0.0051(7) 0.0327(7) -0.0065(7) C12 0.0835(14) 0.0614(13) 0.0797(13) -0.0021(10) 0.0563(11) -0.0097(10) F1 0.166(2) 0.1035(14) 0.168(2) 0.0694(14) 0.1301(19) 0.0414(14) F2 0.1002(13) 0.198(3) 0.1166(15) -0.0126(15) 0.0638(12) -0.0817(17) F3 0.199(2) 0.0845(14) 0.1231(13) -0.0270(11) 0.1334(16) -0.0294(13) F1' 0.166(2) 0.1035(14) 0.168(2) 0.0694(14) 0.1301(19) 0.0414(14) F2' 0.1002(13) 0.198(3) 0.1166(15) -0.0126(15) 0.0638(12) -0.0817(17) F3' 0.199(2) 0.0845(14) 0.1231(13) -0.0270(11) 0.1334(16) -0.0294(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_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.336(2) . ? N1 C5 1.3484(18) . ? N2 N3 1.3285(17) . ? N2 C10 1.352(2) . ? N3 C11 1.332(2) . ? C1 C2 1.379(3) . ? C2 C3 1.371(3) . ? C3 C4 1.388(2) . ? C4 C5 1.401(2) . ? C4 C6 1.493(2) . ? C5 C10 1.468(2) . ? C6 C7 1.531(3) . ? C7 C8 1.516(3) . ? C8 C9 1.504(2) . ? C9 C10 1.3894(19) . ? C9 C11 1.401(2) . ? C11 C12 1.473(2) . ? C12 F3' 1.136(15) . ? C12 F1' 1.171(17) . ? C12 F3 1.315(3) . ? C12 F2 1.316(3) . ? C12 F2' 1.341(16) . ? C12 F1 1.345(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 C1 N1 C5 117.53(16) . . ? N3 N2 C10 113.67(12) . . ? N2 N3 C11 103.78(13) . . ? N1 C1 C2 123.01(17) . . ? C3 C2 C1 118.58(17) . . ? C2 C3 C4 121.05(18) . . ? C3 C4 C5 115.97(15) . . ? C3 C4 C6 120.70(16) . . ? C5 C4 C6 123.32(15) . . ? N1 C5 C4 123.87(14) . . ? N1 C5 C10 112.74(14) . . ? C4 C5 C10 123.38(14) . . ? C4 C6 C7 115.69(15) . . ? C8 C7 C6 114.09(14) . . ? C9 C8 C7 114.73(13) . . ? C10 C9 C11 103.35(13) . . ? C10 C9 C8 128.66(15) . . ? C11 C9 C8 127.96(14) . . ? N2 C10 C9 106.28(13) . . ? N2 C10 C5 118.28(13) . . ? C9 C10 C5 135.44(14) . . ? N3 C11 C9 112.91(14) . . ? N3 C11 C12 118.75(17) . . ? C9 C11 C12 128.33(15) . . ? F3' C12 F1' 106.8(10) . . ? F3' C12 F3 43.9(8) . . ? F1' C12 F3 129.6(6) . . ? F3' C12 F2 129.8(6) . . ? F1' C12 F2 56.1(9) . . ? F3 C12 F2 106.5(2) . . ? F3' C12 F2' 103.3(9) . . ? F1' C12 F2' 100.9(10) . . ? F3 C12 F2' 63.3(7) . . ? F2 C12 F2' 48.4(7) . . ? F3' C12 F1 63.5(8) . . ? F1' C12 F1 51.1(10) . . ? F3 C12 F1 104.7(2) . . ? F2 C12 F1 104.7(2) . . ? F2' C12 F1 134.8(6) . . ? F3' C12 C11 116.0(6) . . ? F1' C12 C11 116.6(6) . . ? F3 C12 C11 113.62(17) . . ? F2 C12 C11 113.34(19) . . ? F2' C12 C11 111.4(6) . . ? F1 C12 C11 113.05(17) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.233 _refine_diff_density_min -0.282 _refine_diff_density_rms 0.047 data_3 _database_code_depnum_ccdc_archive 'CCDC 857978' #TrackingRef '- cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H8 F3 N3' _chemical_formula_weight 239.20 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' _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 7.6053(9) _cell_length_b 16.5396(19) _cell_length_c 8.8177(10) _cell_angle_alpha 90.00 _cell_angle_beta 113.508(2) _cell_angle_gamma 90.00 _cell_volume 1017.1(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3960 _cell_measurement_theta_min 2.46 _cell_measurement_theta_max 27.44 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas not_measured _exptl_crystal_density_diffrn 1.562 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.136 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9353 _exptl_absorpt_correction_T_max 0.9541 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'BRUKER SMART APEXCCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7747 _diffrn_reflns_av_R_equivalents 0.0200 _diffrn_reflns_av_sigmaI/netI 0.0200 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.46 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2340 _reflns_number_gt 2095 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0522P)^2^+0.4992P] 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 2340 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0443 _refine_ls_R_factor_gt 0.0401 _refine_ls_wR_factor_ref 0.1062 _refine_ls_wR_factor_gt 0.1029 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 N1 N 0.55292(16) 0.58185(7) 0.69638(14) 0.0220(2) Uani 1 1 d . . . N2 N 0.28748(16) 0.44484(7) 0.54670(14) 0.0219(2) Uani 1 1 d . . . H2 H 0.3609 0.4523 0.4920 0.026 Uiso 1 1 calc R . . N3 N 0.15795(16) 0.38486(7) 0.51436(14) 0.0228(3) Uani 1 1 d . . . C1 C 0.6581(2) 0.64752(9) 0.76646(17) 0.0252(3) Uani 1 1 d . . . H1 H 0.7562 0.6633 0.7315 0.030 Uiso 1 1 calc R . . C2 C 0.6313(2) 0.69328(9) 0.88649(18) 0.0283(3) Uani 1 1 d . . . H2A H 0.7116 0.7383 0.9350 0.034 Uiso 1 1 calc R . . C3 C 0.4848(2) 0.67213(9) 0.93491(18) 0.0271(3) Uani 1 1 d . . . H3 H 0.4638 0.7027 1.0173 0.033 Uiso 1 1 calc R . . C4 C 0.36929(19) 0.60625(8) 0.86262(16) 0.0226(3) Uani 1 1 d . . . C5 C 0.1914(2) 0.58700(9) 0.89323(18) 0.0276(3) Uani 1 1 d . . . H5A H 0.0835 0.6194 0.8158 0.033 Uiso 1 1 calc R . . H5B H 0.2135 0.6043 1.0069 0.033 Uiso 1 1 calc R . . C6 C 0.1319(2) 0.49791(9) 0.87342(17) 0.0261(3) Uani 1 1 d . . . H6A H 0.2105 0.4678 0.9750 0.031 Uiso 1 1 calc R . . H6B H -0.0043 0.4933 0.8571 0.031 Uiso 1 1 calc R . . C7 C 0.15864(18) 0.46204(8) 0.72827(16) 0.0210(3) Uani 1 1 d . . . C8 C 0.29163(18) 0.49223(8) 0.67306(16) 0.0202(3) Uani 1 1 d . . . C9 C 0.41196(18) 0.56228(8) 0.74496(16) 0.0201(3) Uani 1 1 d . . . C10 C 0.08077(19) 0.39560(8) 0.62510(16) 0.0219(3) Uani 1 1 d . . . C11 C -0.0665(2) 0.33752(9) 0.63023(17) 0.0254(3) Uani 1 1 d . . . F1 F -0.14747(15) 0.29510(6) 0.49189(12) 0.0439(3) Uani 1 1 d . . . F2 F 0.00583(14) 0.28414(6) 0.75344(13) 0.0461(3) Uani 1 1 d . . . F3 F -0.20896(14) 0.37515(6) 0.65457(14) 0.0419(3) 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 N1 0.0232(5) 0.0227(5) 0.0219(5) -0.0005(4) 0.0110(4) 0.0001(4) N2 0.0246(6) 0.0216(5) 0.0242(6) -0.0027(4) 0.0147(5) -0.0022(4) N3 0.0246(6) 0.0211(5) 0.0256(6) -0.0006(4) 0.0129(5) -0.0021(4) C1 0.0248(6) 0.0258(7) 0.0266(7) -0.0002(5) 0.0120(5) -0.0028(5) C2 0.0308(7) 0.0242(7) 0.0298(7) -0.0050(6) 0.0119(6) -0.0045(6) C3 0.0318(7) 0.0261(7) 0.0252(7) -0.0064(5) 0.0132(6) 0.0001(6) C4 0.0242(6) 0.0239(6) 0.0215(6) -0.0006(5) 0.0109(5) 0.0027(5) C5 0.0297(7) 0.0301(7) 0.0296(7) -0.0074(6) 0.0187(6) -0.0009(6) C6 0.0296(7) 0.0301(7) 0.0242(7) -0.0016(5) 0.0168(6) -0.0016(6) C7 0.0225(6) 0.0213(6) 0.0212(6) 0.0019(5) 0.0108(5) 0.0018(5) C8 0.0220(6) 0.0213(6) 0.0197(6) 0.0009(5) 0.0107(5) 0.0027(5) C9 0.0212(6) 0.0208(6) 0.0187(6) 0.0009(5) 0.0084(5) 0.0019(5) C10 0.0230(6) 0.0213(6) 0.0232(6) 0.0020(5) 0.0112(5) 0.0015(5) C11 0.0265(7) 0.0256(7) 0.0261(7) 0.0015(5) 0.0125(6) -0.0019(5) F1 0.0497(6) 0.0474(6) 0.0400(6) -0.0148(4) 0.0234(5) -0.0256(5) F2 0.0414(5) 0.0425(6) 0.0487(6) 0.0232(5) 0.0119(5) -0.0070(4) F3 0.0344(5) 0.0394(5) 0.0643(7) -0.0027(5) 0.0327(5) -0.0041(4) _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 N1 C9 1.3431(17) . ? N1 C1 1.3444(18) . ? N2 N3 1.3460(16) . ? N2 C8 1.3524(17) . ? N3 C10 1.3367(17) . ? C1 C2 1.381(2) . ? C2 C3 1.388(2) . ? C3 C4 1.3853(19) . ? C4 C9 1.4068(18) . ? C4 C5 1.5151(19) . ? C5 C6 1.531(2) . ? C6 C7 1.4965(18) . ? C7 C8 1.3792(18) . ? C7 C10 1.3986(18) . ? C8 C9 1.4556(18) . ? C10 C11 1.4900(18) . ? C11 F1 1.3268(17) . ? C11 F2 1.3362(16) . ? C11 F3 1.3389(17) . ? 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 C9 N1 C1 116.91(11) . . ? N3 N2 C8 112.11(11) . . ? C10 N3 N2 104.17(11) . . ? N1 C1 C2 123.53(13) . . ? C1 C2 C3 118.68(13) . . ? C4 C3 C2 119.76(13) . . ? C3 C4 C9 117.09(13) . . ? C3 C4 C5 122.06(12) . . ? C9 C4 C5 120.52(12) . . ? C4 C5 C6 115.24(11) . . ? C7 C6 C5 110.14(11) . . ? C8 C7 C10 103.58(11) . . ? C8 C7 C6 121.83(12) . . ? C10 C7 C6 134.51(12) . . ? N2 C8 C7 107.55(12) . . ? N2 C8 C9 128.62(12) . . ? C7 C8 C9 123.82(12) . . ? N1 C9 C4 123.98(12) . . ? N1 C9 C8 119.74(11) . . ? C4 C9 C8 116.28(12) . . ? N3 C10 C7 112.60(12) . . ? N3 C10 C11 119.40(12) . . ? C7 C10 C11 127.97(12) . . ? F1 C11 F2 106.73(12) . . ? F1 C11 F3 106.54(12) . . ? F2 C11 F3 105.89(12) . . ? F1 C11 C10 113.07(11) . . ? F2 C11 C10 112.33(11) . . ? F3 C11 C10 111.79(12) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 N1 0.88 2.09 2.8876(16) 149.9 3_666 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.355 _refine_diff_density_min -0.234 _refine_diff_density_rms 0.046 data_4 _database_code_depnum_ccdc_archive 'CCDC 857979' #TrackingRef '- cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H6 F3 N3' _chemical_formula_weight 237.19 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' _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 14.0909(12) _cell_length_b 4.8932(4) _cell_length_c 14.1826(12) _cell_angle_alpha 90.00 _cell_angle_beta 96.014(2) _cell_angle_gamma 90.00 _cell_volume 972.50(14) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1896 _cell_measurement_theta_min 2.89 _cell_measurement_theta_max 25.83 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas not_measured _exptl_crystal_density_diffrn 1.620 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 0.141 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9200 _exptl_absorpt_correction_T_max 0.9888 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'BRUKER SMART APEXCCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6493 _diffrn_reflns_av_R_equivalents 0.0267 _diffrn_reflns_av_sigmaI/netI 0.0327 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2242 _reflns_number_gt 1786 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0661P)^2^+0.7156P] 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 2242 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0645 _refine_ls_R_factor_gt 0.0524 _refine_ls_wR_factor_ref 0.1464 _refine_ls_wR_factor_gt 0.1381 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _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 N1 N 0.61757(11) 0.2190(3) 0.46042(11) 0.0258(4) Uani 1 1 d . . . N2 N 0.49978(11) 0.2061(3) 0.62413(11) 0.0252(4) Uani 1 1 d . . . H2 H 0.4765 0.0850 0.5820 0.030 Uiso 1 1 calc R . . N3 N 0.46542(11) 0.2484(4) 0.70811(11) 0.0289(4) Uani 1 1 d . . . C1 C 0.67666(15) 0.2408(4) 0.39379(15) 0.0318(5) Uani 1 1 d . . . H1 H 0.6663 0.1252 0.3399 0.038 Uiso 1 1 calc R . . C2 C 0.75323(15) 0.4238(5) 0.39832(15) 0.0356(5) Uani 1 1 d . . . H2A H 0.7940 0.4294 0.3491 0.043 Uiso 1 1 calc R . . C3 C 0.76838(15) 0.5946(5) 0.47478(15) 0.0338(5) Uani 1 1 d . . . H3 H 0.8197 0.7213 0.4787 0.041 Uiso 1 1 calc R . . C4 C 0.70802(13) 0.5824(4) 0.54748(13) 0.0269(4) Uani 1 1 d . . . C5 C 0.71968(14) 0.7560(4) 0.62937(14) 0.0294(4) Uani 1 1 d . . . H5 H 0.7690 0.8892 0.6338 0.035 Uiso 1 1 calc R . . C6 C 0.66305(14) 0.7374(4) 0.70060(14) 0.0286(4) Uani 1 1 d . . . H6 H 0.6723 0.8542 0.7543 0.034 Uiso 1 1 calc R . . C7 C 0.58919(12) 0.5376(4) 0.69270(13) 0.0248(4) Uani 1 1 d . . . C8 C 0.57431(12) 0.3720(4) 0.61228(13) 0.0231(4) Uani 1 1 d . . . C9 C 0.63308(12) 0.3877(4) 0.53662(13) 0.0228(4) Uani 1 1 d . . . C10 C 0.51855(13) 0.4471(4) 0.74931(13) 0.0276(4) Uani 1 1 d . . . C11 C 0.49893(15) 0.5398(5) 0.84541(14) 0.0337(5) Uani 1 1 d . . . F1 F 0.56251(14) 0.7201(4) 0.88085(12) 0.0818(7) Uani 1 1 d . . . F2 F 0.41527(12) 0.6551(5) 0.84565(11) 0.0819(7) Uani 1 1 d . . . F3 F 0.50199(16) 0.3399(4) 0.90736(10) 0.0779(6) 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 N1 0.0270(8) 0.0263(8) 0.0242(8) 0.0006(6) 0.0028(6) -0.0008(6) N2 0.0261(8) 0.0263(8) 0.0236(8) -0.0039(6) 0.0049(6) -0.0019(6) N3 0.0284(8) 0.0328(9) 0.0263(8) -0.0031(7) 0.0064(6) 0.0007(7) C1 0.0345(10) 0.0348(11) 0.0266(9) 0.0003(8) 0.0051(8) -0.0025(9) C2 0.0349(11) 0.0421(12) 0.0313(10) 0.0035(9) 0.0104(8) -0.0059(9) C3 0.0308(10) 0.0356(11) 0.0348(11) 0.0046(9) 0.0031(8) -0.0090(9) C4 0.0265(9) 0.0249(10) 0.0284(9) 0.0047(8) -0.0012(7) -0.0003(8) C5 0.0288(9) 0.0247(10) 0.0332(10) 0.0028(8) -0.0045(8) -0.0058(8) C6 0.0317(10) 0.0236(9) 0.0287(10) -0.0028(8) -0.0050(8) 0.0009(8) C7 0.0254(9) 0.0232(9) 0.0254(9) 0.0004(7) 0.0003(7) 0.0049(7) C8 0.0227(8) 0.0208(9) 0.0250(9) 0.0011(7) -0.0012(7) 0.0013(7) C9 0.0227(8) 0.0211(9) 0.0240(9) 0.0030(7) -0.0005(7) 0.0011(7) C10 0.0269(9) 0.0283(10) 0.0276(9) -0.0027(8) 0.0021(7) 0.0036(8) C11 0.0347(11) 0.0371(11) 0.0296(10) -0.0055(9) 0.0048(8) 0.0023(9) F1 0.0870(13) 0.1042(15) 0.0595(11) -0.0531(10) 0.0322(9) -0.0456(11) F2 0.0654(11) 0.1358(18) 0.0461(9) -0.0183(10) 0.0131(8) 0.0522(11) F3 0.1532(19) 0.0546(10) 0.0281(8) 0.0005(7) 0.0199(9) 0.0132(11) _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 N1 C1 1.328(3) . ? N1 C9 1.359(2) . ? N2 N3 1.348(2) . ? N2 C8 1.352(2) . ? N3 C10 1.325(3) . ? C1 C2 1.398(3) . ? C2 C3 1.368(3) . ? C3 C4 1.405(3) . ? C4 C9 1.418(3) . ? C4 C5 1.435(3) . ? C5 C6 1.354(3) . ? C6 C7 1.423(3) . ? C7 C8 1.397(3) . ? C7 C10 1.414(3) . ? C8 C9 1.425(3) . ? C10 C11 1.489(3) . ? C11 F2 1.307(3) . ? C11 F3 1.313(3) . ? C11 F1 1.319(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 C1 N1 C9 117.17(17) . . ? N3 N2 C8 111.92(15) . . ? C10 N3 N2 105.29(16) . . ? N1 C1 C2 123.86(19) . . ? C3 C2 C1 118.88(19) . . ? C2 C3 C4 119.98(19) . . ? C3 C4 C9 116.74(18) . . ? C3 C4 C5 122.84(18) . . ? C9 C4 C5 120.43(18) . . ? C6 C5 C4 122.51(18) . . ? C5 C6 C7 118.07(18) . . ? C8 C7 C10 103.15(16) . . ? C8 C7 C6 120.57(18) . . ? C10 C7 C6 136.29(18) . . ? N2 C8 C7 107.40(16) . . ? N2 C8 C9 130.27(17) . . ? C7 C8 C9 122.31(17) . . ? N1 C9 C4 123.36(17) . . ? N1 C9 C8 120.57(16) . . ? C4 C9 C8 116.05(17) . . ? N3 C10 C7 112.24(17) . . ? N3 C10 C11 118.45(18) . . ? C7 C10 C11 129.30(18) . . ? F2 C11 F3 106.6(2) . . ? F2 C11 F1 106.7(2) . . ? F3 C11 F1 105.67(19) . . ? F2 C11 C10 112.82(17) . . ? F3 C11 C10 112.92(18) . . ? F1 C11 C10 111.63(18) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 N1 0.88 2.04 2.843(2) 151.1 3_656 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.492 _refine_diff_density_min -0.358 _refine_diff_density_rms 0.055 # Attachment '- cif.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 870226' #TrackingRef '- cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H6 F3 N3' _chemical_formula_weight 213.17 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 22.7575(15) _cell_length_b 4.3553(3) _cell_length_c 17.9810(10) _cell_angle_alpha 90.00 _cell_angle_beta 94.239(3) _cell_angle_gamma 90.00 _cell_volume 1777.3(2) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5141 _cell_measurement_theta_min 1.79 _cell_measurement_theta_max 27.50 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.593 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 0.144 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.924 _exptl_absorpt_correction_T_max 0.998 _exptl_absorpt_process_details 'SORTAV, Blessing 1995' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'NONIUS KappaCCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5141 _diffrn_reflns_av_R_equivalents 0.0323 _diffrn_reflns_av_sigmaI/netI 0.0351 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2023 _reflns_number_gt 1493 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'NONIUS COLLECT' _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _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^)+(0.0639P)^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_number_reflns 2023 _refine_ls_number_parameters 140 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0598 _refine_ls_R_factor_gt 0.0399 _refine_ls_wR_factor_ref 0.1125 _refine_ls_wR_factor_gt 0.1045 _refine_ls_goodness_of_fit_ref 1.100 _refine_ls_restrained_S_all 1.100 _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 N1 N 0.03780(5) 0.9904(3) 0.66264(6) 0.0345(3) Uani 1 1 d . . . N2 N 0.07294(5) 0.7303(3) 0.80377(6) 0.0330(3) Uani 1 1 d . . . H2 H 0.0364(7) 0.811(4) 0.8064(9) 0.045(5) Uiso 1 1 d . . . N3 N 0.09636(5) 0.5690(3) 0.86241(6) 0.0337(3) Uani 1 1 d . . . C1 C 0.02342(6) 1.1484(4) 0.59998(8) 0.0415(4) Uani 1 1 d . . . H1 H -0.0172 1.1813 0.5860 0.050 Uiso 1 1 calc R . . C2 C 0.06432(7) 1.2659(4) 0.55464(8) 0.0425(4) Uani 1 1 d . . . H2A H 0.0521 1.3745 0.5104 0.051 Uiso 1 1 calc R . . C3 C 0.12340(7) 1.2224(3) 0.57498(8) 0.0392(4) Uani 1 1 d . . . H3 H 0.1526 1.3018 0.5452 0.047 Uiso 1 1 calc R . . C4 C 0.13923(6) 1.0611(3) 0.63951(8) 0.0350(3) Uani 1 1 d . . . H4 H 0.1796 1.0289 0.6548 0.042 Uiso 1 1 calc R . . C5 C 0.09555(6) 0.9465(3) 0.68179(7) 0.0303(3) Uani 1 1 d . . . C6 C 0.11112(6) 0.7738(3) 0.75039(7) 0.0298(3) Uani 1 1 d . . . C7 C 0.16262(6) 0.6289(3) 0.77539(7) 0.0307(3) Uani 1 1 d . . . H7 H 0.1982 0.6154 0.7511 0.037 Uiso 1 1 calc R . . C8 C 0.15077(6) 0.5063(3) 0.84438(7) 0.0299(3) Uani 1 1 d . . . C9 C 0.19176(6) 0.3397(3) 0.89827(7) 0.0329(4) Uani 1 1 d . . . F1 F 0.23036(3) 0.16770(19) 0.86311(5) 0.0415(3) Uani 1 1 d . . . F2 F 0.22514(4) 0.52982(19) 0.94266(5) 0.0438(3) Uani 1 1 d . . . F3 F 0.16413(4) 0.1545(2) 0.94287(5) 0.0487(3) 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 N1 0.0317(6) 0.0444(8) 0.0276(6) -0.0010(5) 0.0036(5) 0.0017(5) N2 0.0267(6) 0.0447(8) 0.0279(6) 0.0024(5) 0.0035(5) 0.0008(6) N3 0.0303(6) 0.0433(7) 0.0273(6) 0.0023(5) 0.0013(5) -0.0024(5) C1 0.0355(8) 0.0555(10) 0.0334(8) 0.0017(7) 0.0028(6) 0.0093(7) C2 0.0498(9) 0.0482(10) 0.0300(8) 0.0063(7) 0.0072(7) 0.0117(8) C3 0.0439(8) 0.0432(9) 0.0319(8) 0.0019(7) 0.0122(6) 0.0011(7) C4 0.0303(7) 0.0424(9) 0.0331(7) -0.0011(7) 0.0073(6) 0.0002(6) C5 0.0317(7) 0.0333(8) 0.0262(7) -0.0034(6) 0.0043(6) 0.0004(6) C6 0.0290(7) 0.0348(8) 0.0260(7) -0.0036(6) 0.0049(5) -0.0032(6) C7 0.0293(7) 0.0347(8) 0.0285(7) -0.0030(6) 0.0043(5) -0.0012(6) C8 0.0294(7) 0.0329(8) 0.0275(7) -0.0024(6) 0.0020(5) -0.0028(6) C9 0.0338(8) 0.0331(8) 0.0320(8) 0.0000(6) 0.0036(6) -0.0031(6) F1 0.0400(5) 0.0411(5) 0.0437(5) -0.0042(4) 0.0043(4) 0.0081(4) F2 0.0470(5) 0.0423(5) 0.0398(5) -0.0056(4) -0.0126(4) 0.0020(4) F3 0.0457(5) 0.0526(6) 0.0488(6) 0.0199(5) 0.0090(4) 0.0011(4) _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 N1 C1 1.3400(18) . ? N1 C5 1.3473(17) . ? N2 N3 1.3440(16) . ? N2 C6 1.3547(17) . ? N3 C8 1.3312(17) . ? C1 C2 1.380(2) . ? C2 C3 1.380(2) . ? C3 C4 1.381(2) . ? C4 C5 1.3881(19) . ? C5 C6 1.4656(18) . ? C6 C7 1.3770(19) . ? C7 C8 1.3950(18) . ? C8 C9 1.4839(19) . ? C9 F3 1.3283(15) . ? C9 F2 1.3454(16) . ? C9 F1 1.3472(16) . ? 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 C1 N1 C5 117.43(12) . . ? N3 N2 C6 113.03(11) . . ? C8 N3 N2 103.77(11) . . ? N1 C1 C2 123.62(14) . . ? C3 C2 C1 118.61(14) . . ? C2 C3 C4 118.75(13) . . ? C3 C4 C5 119.34(13) . . ? N1 C5 C4 122.25(13) . . ? N1 C5 C6 117.28(12) . . ? C4 C5 C6 120.47(12) . . ? N2 C6 C7 106.23(12) . . ? N2 C6 C5 122.71(12) . . ? C7 C6 C5 131.06(12) . . ? C6 C7 C8 104.47(12) . . ? N3 C8 C7 112.50(12) . . ? N3 C8 C9 119.49(12) . . ? C7 C8 C9 127.90(12) . . ? F3 C9 F2 106.70(10) . . ? F3 C9 F1 107.44(11) . . ? F2 C9 F1 105.15(11) . . ? F3 C9 C8 112.86(11) . . ? F2 C9 C8 112.75(12) . . ? F1 C9 C8 111.46(10) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 N1 0.907(16) 1.978(17) 2.8678(17) 166.5(14) 2_556 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.193 _refine_diff_density_min -0.217 _refine_diff_density_rms 0.044