# Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full J.Mater.Chem. _journal_coden_cambridge 1145 #TrackingRef 'shrv110-final.cif' #=========================================================================== _audit_creation_date 2010-04-19 _audit_creation_method 'from SHELXTL CIF, local template and enCIFer' _audit_update_record ; ; #=========================================================================== # 1. SUBMISSION DETAILS #=========================================================================== _publ_contact_author_name 'Dr Damon A. Parrish' _publ_contact_author_address ; Laboratory for the Structure of Matter Naval Research Laboratory Washington, DC 20375 ; _publ_contact_author_email damon.parrish@nrl.navy.mil _publ_contact_author_fax 202-767-6874 _publ_contact_author_phone 202-404-2141 _publ_requested_category ? _publ_requested_coeditor_name ? _publ_contact_letter ; ; #=========================================================================== # 2. PROCESSING SUMMARY (IUCr Office Use Only) # Do NOT alter anthing in this section. #=========================================================================== _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ; ? ; _journal_techeditor_code ? _journal_techeditor_notes ; ? ; _journal_coden_ASTM ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #=========================================================================== # 3. TITLE AND AUTHOR LIST #=========================================================================== _publ_section_title ; title ; loop_ _publ_author_name _publ_author_address _publ_author_footnote D.A.Parrish ; Laboratory for the Structure of Matter, Code 6030 Naval Research Laboratory Washington, DC 20375 ; ? J.Shreeve ; Chemsitry Department University of Idaho Moscow, ID, 83843 ; ? S.Garg ; Chemsitry Department University of Idaho Moscow, ID, 83843 ; ? #=========================================================================== # 4. TEXT #=========================================================================== _publ_section_abstract ; ; _publ_section_comment ; ; _publ_section_exptl_prep ; ; _publ_section_exptl_refinement ; ; _publ_section_references ; Bruker (2009). PROTEUM v2009.7-0. Bruker AXS Inc., Madison, Wisconsin, USA. Bruker (2009). SAINT v7.66A. Bruker AXS Inc., Madison, Wisconsin, USA. Bruker (2008). SADABS v2008/1, Bruker AXS Inc., Madison, Wisconsin, USA. Bruker (2008). XPREP v2008/2. Bruker AXS Inc., Madison, Wisconsin, USA. Bruker (2008). SHELXTL v2008/4. Bruker AXS Inc., Madison, Wisconsin, USA. ; _publ_section_figure_captions ; ; _publ_section_table_legends ; ; _publ_section_acknowledgements ; Crystallographic studies were supported in part by the Office of Naval Research (ONR) and the Naval Research Laboratory (NRL). ; #========================================================================== data_shrv110 _database_code_depnum_ccdc_archive 'CCDC 796564' #TrackingRef 'shrv110-final.cif' _audit_creation_date 2010-04-19 _audit_creation_method 'from SHELXTL CIF, local template and enCIFer' _chemical_name_systematic ; ? 1,1'-(2,2-bis((4-(trifluoromethyl)-1H-1,2,3-triazol-1-yl)methyl) propane-1,3-diyl)bis(4-(trifluoromethyl)-1H-1,2,3-triazole)? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H12 F12 N12' _chemical_formula_sum 'C17 H12 F12 N12' _chemical_formula_weight 612.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M I-4 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'y, -x, -z' '-y, x, -z' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1/2, z+1/2' 'y+1/2, -x+1/2, -z+1/2' '-y+1/2, x+1/2, -z+1/2' _cell_length_a 11.8876(11) _cell_length_b 11.8876(11) _cell_length_c 8.2416(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1164.7(2) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description irregular _exptl_crystal_colour colorless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.746 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 612 _exptl_absorpt_coefficient_mu 1.647 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS v2008/1 (Bruker, 2008)' _exptl_absorpt_correction_T_min 0.6154 _exptl_absorpt_correction_T_max 0.7530 _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator 'Helios optics' _diffrn_measurement_device 'Bruker PLATINUM 135 CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 3190 _diffrn_reflns_av_R_equivalents 0.1695 _diffrn_reflns_av_sigmaI/netI 0.0798 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 5.26 _diffrn_reflns_theta_max 68.25 _reflns_number_total 1000 _reflns_number_gt 992 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker PROTEUM v2009.7-0 (Bruker, 2009)' _computing_cell_refinement 'Bruker PROTEUM v2009.7-0 (Bruker, 2009)' _computing_data_reduction ; Bruker SAINT v7.66A (Bruker, 2009), Bruker XPREP v2008/2 (Bruker, 2008) ; _computing_structure_solution 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _computing_structure_refinement 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _computing_molecular_graphics 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _computing_publication_material 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _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^)+(0.1197P)^2^+0.1979P] 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 SHELXL _refine_ls_extinction_coef 0.0045(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.2(3) _refine_ls_number_reflns 1000 _refine_ls_number_parameters 95 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0608 _refine_ls_R_factor_gt 0.0607 _refine_ls_wR_factor_ref 0.1554 _refine_ls_wR_factor_gt 0.1553 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _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 C1 C -0.5000 0.0000 -0.2500 0.0284(9) Uani 1 4 d S . . C2 C -0.5660(2) -0.07842(17) -0.1347(3) 0.0349(6) Uani 1 1 d . . . H2A H -0.5145 -0.1056 -0.0505 0.042 Uiso 1 1 calc R . . H2B H -0.6248 -0.0343 -0.0809 0.042 Uiso 1 1 calc R . . N3 N -0.61826(15) -0.17530(17) -0.2127(3) 0.0327(5) Uani 1 1 d . . . N4 N -0.7020(2) -0.1631(2) -0.3228(4) 0.0482(7) Uani 1 1 d . . . N5 N -0.7374(2) -0.2638(2) -0.3617(4) 0.0500(7) Uani 1 1 d . . . C6 C -0.6761(2) -0.3393(2) -0.2762(3) 0.0347(6) Uani 1 1 d . . . C7 C -0.5990(2) -0.2851(2) -0.1824(3) 0.0355(6) Uani 1 1 d . . . H7 H -0.5451 -0.3169 -0.1128 0.043 Uiso 1 1 calc R . . C8 C -0.6961(2) -0.4620(2) -0.2902(4) 0.0431(6) Uani 1 1 d . . . F9 F -0.6281(2) -0.51924(15) -0.1917(4) 0.0695(7) Uani 1 1 d . . . F10 F -0.80154(18) -0.48986(19) -0.2496(4) 0.0788(10) Uani 1 1 d . . . F11 F -0.6834(2) -0.5000(2) -0.4391(3) 0.0744(8) 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 C1 0.0283(12) 0.0283(12) 0.029(2) 0.000 0.000 0.000 C2 0.0377(11) 0.0292(11) 0.0376(15) -0.0018(8) 0.0040(10) -0.0027(9) N3 0.0276(9) 0.0306(9) 0.0399(10) 0.0011(8) 0.0014(8) -0.0004(7) N4 0.0385(11) 0.0401(12) 0.0661(16) 0.0043(10) -0.0143(11) 0.0013(9) N5 0.0398(12) 0.0393(12) 0.0710(17) 0.0033(11) -0.0144(12) -0.0009(10) C6 0.0311(10) 0.0370(13) 0.0360(14) 0.0020(9) 0.0049(9) -0.0025(8) C7 0.0394(11) 0.0296(11) 0.0376(13) 0.0064(9) -0.0032(9) -0.0036(9) C8 0.0441(14) 0.0375(13) 0.0476(15) 0.0007(12) -0.0061(11) -0.0083(10) F9 0.0785(14) 0.0376(9) 0.0925(16) 0.0115(10) -0.0309(12) -0.0063(9) F10 0.0594(12) 0.0599(12) 0.117(3) 0.0056(12) 0.0116(13) -0.0291(9) F11 0.1024(19) 0.0557(11) 0.0652(15) -0.0204(10) 0.0009(12) -0.0069(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 C1 C2 1.545(2) 2_455 ? C1 C2 1.545(2) 7_444 ? C1 C2 1.545(2) 8_454 ? C1 C2 1.545(2) . ? C2 N3 1.458(3) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? N3 C7 1.349(3) . ? N3 N4 1.355(3) . ? N4 N5 1.309(4) . ? N5 C6 1.353(4) . ? C6 C7 1.360(4) . ? C6 C8 1.483(3) . ? C7 H7 0.9400 . ? C8 F11 1.316(4) . ? C8 F9 1.332(4) . ? C8 F10 1.339(4) . ? 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 C2 C1 C2 112.23(10) 2_455 7_444 ? C2 C1 C2 112.23(10) 2_455 8_454 ? C2 C1 C2 104.09(19) 7_444 8_454 ? C2 C1 C2 104.09(19) 2_455 . ? C2 C1 C2 112.23(10) 7_444 . ? C2 C1 C2 112.23(10) 8_454 . ? N3 C2 C1 114.94(18) . . ? N3 C2 H2A 108.5 . . ? C1 C2 H2A 108.5 . . ? N3 C2 H2B 108.5 . . ? C1 C2 H2B 108.5 . . ? H2A C2 H2B 107.5 . . ? C7 N3 N4 110.6(2) . . ? C7 N3 C2 127.6(2) . . ? N4 N3 C2 121.6(2) . . ? N5 N4 N3 107.6(2) . . ? N4 N5 C6 107.8(2) . . ? N5 C6 C7 110.2(2) . . ? N5 C6 C8 121.7(2) . . ? C7 C6 C8 128.1(2) . . ? N3 C7 C6 103.8(2) . . ? N3 C7 H7 128.1 . . ? C6 C7 H7 128.1 . . ? F11 C8 F9 108.9(3) . . ? F11 C8 F10 104.8(3) . . ? F9 C8 F10 106.8(3) . . ? F11 C8 C6 113.0(3) . . ? F9 C8 C6 111.0(2) . . ? F10 C8 C6 112.0(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 C1 C2 N3 -168.4(2) 2_455 . . . ? C2 C1 C2 N3 70.0(3) 7_444 . . . ? C2 C1 C2 N3 -46.8(2) 8_454 . . . ? C1 C2 N3 C7 119.6(2) . . . . ? C1 C2 N3 N4 -65.2(3) . . . . ? C7 N3 N4 N5 0.7(3) . . . . ? C2 N3 N4 N5 -175.3(2) . . . . ? N3 N4 N5 C6 0.1(4) . . . . ? N4 N5 C6 C7 -0.8(4) . . . . ? N4 N5 C6 C8 179.1(3) . . . . ? N4 N3 C7 C6 -1.2(3) . . . . ? C2 N3 C7 C6 174.5(2) . . . . ? N5 C6 C7 N3 1.2(3) . . . . ? C8 C6 C7 N3 -178.7(3) . . . . ? N5 C6 C8 F11 59.1(4) . . . . ? C7 C6 C8 F11 -121.0(3) . . . . ? N5 C6 C8 F9 -178.3(3) . . . . ? C7 C6 C8 F9 1.6(4) . . . . ? N5 C6 C8 F10 -59.0(4) . . . . ? C7 C6 C8 F10 120.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 68.25 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.292 _refine_diff_density_min -0.317 _refine_diff_density_rms 0.080 # Attachment 'shrv119-final.cif' data_shrv119 _database_code_depnum_ccdc_archive 'CCDC 796565' #TrackingRef 'shrv119-final.cif' _audit_creation_date 2010-06-23 _audit_creation_method 'from SHELXTL CIF, local template and enCIFer' _chemical_name_systematic ; tris(2-(4-(trifluoromethyl)-1H-1,2,3-triazol-1-yl)ethyl)amine ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H15 F9 N10' _chemical_formula_sum 'C15 H15 F9 N10' _chemical_formula_weight 506.37 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 9.7121(14) _cell_length_b 14.214(2) _cell_length_c 15.290(2) _cell_angle_alpha 90.00 _cell_angle_beta 104.906(2) _cell_angle_gamma 90.00 _cell_volume 2039.8(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'irregular prism' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.649 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1024 _exptl_absorpt_coefficient_mu 0.165 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS v2008/1 (Bruker, 2008)' _exptl_absorpt_correction_T_min 0.6495 _exptl_absorpt_correction_T_max 0.7457 _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 APEX II CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 21138 _diffrn_reflns_av_R_equivalents 0.0386 _diffrn_reflns_av_sigmaI/netI 0.0334 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 28.40 _reflns_number_total 5063 _reflns_number_gt 3785 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2 v2009.3-0 (Bruker, 2009)' _computing_cell_refinement 'Bruker APEX2 v2009.3-0 (Bruker, 2009)' _computing_data_reduction ; Bruker SAINT v7.60A (Bruker, 2009), Bruker XPREP v2008/2 (Bruker, 2008) ; _computing_structure_solution 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _computing_structure_refinement 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _computing_molecular_graphics 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _computing_publication_material 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _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^)+(0.0376P)^2^+0.9602P] 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 5063 _refine_ls_number_parameters 307 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0614 _refine_ls_R_factor_gt 0.0418 _refine_ls_wR_factor_ref 0.1008 _refine_ls_wR_factor_gt 0.0913 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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 1.23531(13) 0.63498(9) 0.24919(9) 0.0179(3) Uani 1 1 d . . . C2 C 1.24833(16) 0.73336(11) 0.22251(11) 0.0219(3) Uani 1 1 d . . . H2A H 1.3455 0.7437 0.2151 0.026 Uiso 1 1 calc R . . H2B H 1.2357 0.7752 0.2716 0.026 Uiso 1 1 calc R . . C3 C 1.14106(17) 0.76003(12) 0.13558(11) 0.0219(3) Uani 1 1 d . . . H3A H 1.1645 0.8234 0.1167 0.026 Uiso 1 1 calc R . . H3B H 1.1481 0.7150 0.0875 0.026 Uiso 1 1 calc R . . N4 N 0.99393(14) 0.76033(9) 0.14473(9) 0.0189(3) Uani 1 1 d . . . N5 N 0.96526(14) 0.78778(10) 0.22253(9) 0.0236(3) Uani 1 1 d . . . N6 N 0.82595(14) 0.79059(10) 0.20795(9) 0.0239(3) Uani 1 1 d . . . C7 C 0.76742(17) 0.76597(11) 0.12057(11) 0.0214(3) Uani 1 1 d . . . C8 C 0.87372(17) 0.74629(11) 0.07958(11) 0.0215(3) Uani 1 1 d . . . H8 H 0.8645 0.7271 0.0188 0.026 Uiso 1 1 calc R . . C9 C 0.61127(18) 0.76749(13) 0.08162(12) 0.0278(4) Uani 1 1 d . . . F10 F 0.57704(11) 0.74031(9) -0.00488(7) 0.0402(3) Uani 1 1 d . . . F11 F 0.55617(11) 0.85408(8) 0.08304(8) 0.0426(3) Uani 1 1 d . . . F12 F 0.53991(11) 0.71223(9) 0.12516(9) 0.0459(3) Uani 1 1 d . . . C13 C 1.29687(16) 0.57197(11) 0.19266(11) 0.0188(3) Uani 1 1 d . . . H13A H 1.4021 0.5747 0.2138 0.023 Uiso 1 1 calc R . . H13B H 1.2690 0.5947 0.1293 0.023 Uiso 1 1 calc R . . C14 C 1.24919(16) 0.47065(11) 0.19506(11) 0.0207(3) Uani 1 1 d . . . H14A H 1.3088 0.4300 0.1670 0.025 Uiso 1 1 calc R . . H14B H 1.2642 0.4507 0.2589 0.025 Uiso 1 1 calc R . . N15 N 1.09890(13) 0.45717(9) 0.14748(9) 0.0178(3) Uani 1 1 d . . . N16 N 1.06282(15) 0.39153(10) 0.08229(9) 0.0228(3) Uani 1 1 d . . . N17 N 0.92302(15) 0.39212(10) 0.05237(9) 0.0237(3) Uani 1 1 d . . . C18 C 0.87165(16) 0.45839(11) 0.09958(10) 0.0189(3) Uani 1 1 d . . . C19 C 0.98256(16) 0.50036(11) 0.16064(10) 0.0184(3) Uani 1 1 d . . . H19 H 0.9784 0.5488 0.2027 0.022 Uiso 1 1 calc R . . C20 C 0.71635(17) 0.47593(12) 0.08192(11) 0.0236(3) Uani 1 1 d . . . F21 F 0.68866(11) 0.54013(9) 0.13808(8) 0.0435(3) Uani 1 1 d . . . F22 F 0.64416(12) 0.39912(8) 0.09191(10) 0.0526(4) Uani 1 1 d . . . F23 F 0.65940(12) 0.50805(10) -0.00117(8) 0.0461(3) Uani 1 1 d . . . C24 C 1.30619(16) 0.62183(12) 0.34550(10) 0.0222(3) Uani 1 1 d . . . H24A H 1.3979 0.6562 0.3601 0.027 Uiso 1 1 calc R . . H24B H 1.3273 0.5542 0.3572 0.027 Uiso 1 1 calc R . . C25 C 1.21634(16) 0.65636(13) 0.40738(11) 0.0232(3) Uani 1 1 d . . . H25A H 1.2718 0.6499 0.4712 0.028 Uiso 1 1 calc R . . H25B H 1.1945 0.7239 0.3955 0.028 Uiso 1 1 calc R . . N26 N 1.08265(13) 0.60385(9) 0.39399(9) 0.0189(3) Uani 1 1 d . . . N27 N 1.08344(14) 0.50920(10) 0.39932(10) 0.0233(3) Uani 1 1 d . . . N28 N 0.95089(14) 0.48163(10) 0.38816(10) 0.0236(3) Uani 1 1 d . . . C29 C 0.86728(16) 0.55950(12) 0.37581(11) 0.0207(3) Uani 1 1 d . . . C30 C 0.94928(16) 0.63791(12) 0.37894(10) 0.0197(3) Uani 1 1 d . . . H30 H 0.9193 0.7017 0.3721 0.024 Uiso 1 1 calc R . . C31 C 0.71070(17) 0.55297(13) 0.36255(12) 0.0268(4) Uani 1 1 d . . . F32 F 0.67117(11) 0.54614(11) 0.43940(8) 0.0541(4) Uani 1 1 d . . . F33 F 0.64503(11) 0.62846(8) 0.31911(8) 0.0407(3) Uani 1 1 d . . . F34 F 0.65442(12) 0.47821(9) 0.31299(9) 0.0468(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 0.0170(6) 0.0181(7) 0.0186(6) -0.0028(5) 0.0048(5) -0.0006(5) C2 0.0209(7) 0.0184(8) 0.0275(9) -0.0051(6) 0.0081(7) -0.0033(6) C3 0.0243(8) 0.0176(8) 0.0269(8) 0.0019(6) 0.0123(7) 0.0006(6) N4 0.0247(7) 0.0155(6) 0.0182(6) -0.0005(5) 0.0084(5) 0.0021(5) N5 0.0258(7) 0.0255(7) 0.0212(7) -0.0035(6) 0.0093(6) 0.0018(6) N6 0.0261(7) 0.0242(7) 0.0227(7) -0.0014(6) 0.0088(6) 0.0028(6) C7 0.0247(8) 0.0182(8) 0.0214(8) 0.0015(6) 0.0061(6) 0.0029(6) C8 0.0270(8) 0.0194(8) 0.0178(7) 0.0004(6) 0.0054(6) 0.0012(6) C9 0.0277(9) 0.0267(9) 0.0288(9) 0.0026(7) 0.0068(7) 0.0042(7) F10 0.0309(6) 0.0521(8) 0.0324(6) -0.0080(5) -0.0015(5) 0.0003(5) F11 0.0326(6) 0.0347(6) 0.0559(8) -0.0016(5) 0.0033(5) 0.0142(5) F12 0.0275(6) 0.0551(8) 0.0587(8) 0.0197(6) 0.0174(5) 0.0023(5) C13 0.0178(7) 0.0194(8) 0.0201(8) -0.0012(6) 0.0068(6) -0.0002(6) C14 0.0179(7) 0.0196(8) 0.0234(8) 0.0001(6) 0.0031(6) 0.0005(6) N15 0.0208(6) 0.0151(6) 0.0172(6) -0.0012(5) 0.0046(5) -0.0007(5) N16 0.0261(7) 0.0207(7) 0.0205(7) -0.0049(6) 0.0040(6) 0.0000(6) N17 0.0259(7) 0.0224(7) 0.0209(7) -0.0037(6) 0.0025(6) 0.0002(6) C18 0.0224(7) 0.0159(8) 0.0179(8) 0.0000(6) 0.0041(6) -0.0010(6) C19 0.0207(7) 0.0174(8) 0.0176(7) -0.0009(6) 0.0060(6) 0.0004(6) C20 0.0232(8) 0.0227(8) 0.0234(8) -0.0005(7) 0.0029(7) -0.0013(7) F21 0.0272(5) 0.0599(8) 0.0445(7) -0.0222(6) 0.0113(5) 0.0040(5) F22 0.0248(6) 0.0316(6) 0.0954(11) 0.0129(7) 0.0044(6) -0.0089(5) F23 0.0308(6) 0.0773(9) 0.0287(6) 0.0160(6) 0.0047(5) 0.0204(6) C24 0.0146(7) 0.0317(9) 0.0196(8) -0.0037(7) 0.0033(6) -0.0013(6) C25 0.0194(7) 0.0299(9) 0.0203(8) -0.0077(7) 0.0051(6) -0.0064(7) N26 0.0188(6) 0.0204(7) 0.0182(6) -0.0028(5) 0.0059(5) 0.0002(5) N27 0.0226(7) 0.0214(7) 0.0260(7) -0.0005(6) 0.0063(6) 0.0024(6) N28 0.0234(7) 0.0210(7) 0.0274(8) -0.0009(6) 0.0085(6) 0.0005(6) C29 0.0204(7) 0.0238(8) 0.0184(8) 0.0005(6) 0.0059(6) 0.0014(6) C30 0.0195(7) 0.0217(8) 0.0187(8) 0.0013(6) 0.0063(6) 0.0036(6) C31 0.0217(8) 0.0329(10) 0.0256(9) 0.0046(7) 0.0059(7) 0.0000(7) F32 0.0248(6) 0.1090(12) 0.0318(6) 0.0144(7) 0.0135(5) 0.0011(6) F33 0.0208(5) 0.0426(7) 0.0568(8) 0.0147(6) 0.0069(5) 0.0061(5) F34 0.0281(6) 0.0441(7) 0.0643(8) -0.0090(6) 0.0047(6) -0.0126(5) _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 C24 1.468(2) . ? N1 C2 1.471(2) . ? N1 C13 1.4738(19) . ? C2 C3 1.511(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 N4 1.4711(19) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? N4 C8 1.341(2) . ? N4 N5 1.3473(18) . ? N5 N6 1.3140(19) . ? N6 C7 1.356(2) . ? C7 C8 1.367(2) . ? C7 C9 1.480(2) . ? C8 H8 0.9500 . ? C9 F12 1.333(2) . ? C9 F10 1.335(2) . ? C9 F11 1.344(2) . ? C13 C14 1.516(2) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 N15 1.4664(19) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? N15 N16 1.3443(18) . ? N15 C19 1.3457(19) . ? N16 N17 1.3166(19) . ? N17 C18 1.357(2) . ? C18 C19 1.368(2) . ? C18 C20 1.483(2) . ? C19 H19 0.9500 . ? C20 F21 1.327(2) . ? C20 F22 1.327(2) . ? C20 F23 1.329(2) . ? C24 C25 1.524(2) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 N26 1.466(2) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? N26 C30 1.3460(19) . ? N26 N27 1.3477(19) . ? N27 N28 1.3141(19) . ? N28 C29 1.357(2) . ? C29 C30 1.363(2) . ? C29 C31 1.484(2) . ? C30 H30 0.9500 . ? C31 F32 1.330(2) . ? C31 F33 1.335(2) . ? C31 F34 1.338(2) . ? 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 C24 N1 C2 110.33(12) . . ? C24 N1 C13 110.77(12) . . ? C2 N1 C13 109.77(12) . . ? N1 C2 C3 113.17(13) . . ? N1 C2 H2A 108.9 . . ? C3 C2 H2A 108.9 . . ? N1 C2 H2B 108.9 . . ? C3 C2 H2B 108.9 . . ? H2A C2 H2B 107.8 . . ? N4 C3 C2 112.57(13) . . ? N4 C3 H3A 109.1 . . ? C2 C3 H3A 109.1 . . ? N4 C3 H3B 109.1 . . ? C2 C3 H3B 109.1 . . ? H3A C3 H3B 107.8 . . ? C8 N4 N5 111.16(13) . . ? C8 N4 C3 127.62(13) . . ? N5 N4 C3 120.74(13) . . ? N6 N5 N4 107.26(12) . . ? N5 N6 C7 108.15(13) . . ? N6 C7 C8 109.25(14) . . ? N6 C7 C9 121.27(14) . . ? C8 C7 C9 129.41(16) . . ? N4 C8 C7 104.17(14) . . ? N4 C8 H8 127.9 . . ? C7 C8 H8 127.9 . . ? F12 C9 F10 107.17(15) . . ? F12 C9 F11 105.72(14) . . ? F10 C9 F11 106.39(14) . . ? F12 C9 C7 113.63(14) . . ? F10 C9 C7 111.27(14) . . ? F11 C9 C7 112.20(15) . . ? N1 C13 C14 112.99(12) . . ? N1 C13 H13A 109.0 . . ? C14 C13 H13A 109.0 . . ? N1 C13 H13B 109.0 . . ? C14 C13 H13B 109.0 . . ? H13A C13 H13B 107.8 . . ? N15 C14 C13 112.54(13) . . ? N15 C14 H14A 109.1 . . ? C13 C14 H14A 109.1 . . ? N15 C14 H14B 109.1 . . ? C13 C14 H14B 109.1 . . ? H14A C14 H14B 107.8 . . ? N16 N15 C19 111.02(13) . . ? N16 N15 C14 119.66(12) . . ? C19 N15 C14 129.28(13) . . ? N17 N16 N15 107.58(12) . . ? N16 N17 C18 107.87(13) . . ? N17 C18 C19 109.45(14) . . ? N17 C18 C20 121.03(14) . . ? C19 C18 C20 129.52(15) . . ? N15 C19 C18 104.07(14) . . ? N15 C19 H19 128.0 . . ? C18 C19 H19 128.0 . . ? F21 C20 F22 106.87(14) . . ? F21 C20 F23 106.17(14) . . ? F22 C20 F23 106.87(14) . . ? F21 C20 C18 111.32(13) . . ? F22 C20 C18 112.54(14) . . ? F23 C20 C18 112.66(14) . . ? N1 C24 C25 112.72(13) . . ? N1 C24 H24A 109.0 . . ? C25 C24 H24A 109.0 . . ? N1 C24 H24B 109.0 . . ? C25 C24 H24B 109.0 . . ? H24A C24 H24B 107.8 . . ? N26 C25 C24 112.17(13) . . ? N26 C25 H25A 109.2 . . ? C24 C25 H25A 109.2 . . ? N26 C25 H25B 109.2 . . ? C24 C25 H25B 109.2 . . ? H25A C25 H25B 107.9 . . ? C30 N26 N27 111.08(13) . . ? C30 N26 C25 128.29(14) . . ? N27 N26 C25 120.59(13) . . ? N28 N27 N26 107.44(12) . . ? N27 N28 C29 107.82(13) . . ? N28 C29 C30 109.79(14) . . ? N28 C29 C31 121.56(15) . . ? C30 C29 C31 128.65(15) . . ? N26 C30 C29 103.87(14) . . ? N26 C30 H30 128.1 . . ? C29 C30 H30 128.1 . . ? F32 C31 F33 106.79(15) . . ? F32 C31 F34 105.89(15) . . ? F33 C31 F34 106.46(14) . . ? F32 C31 C29 113.71(14) . . ? F33 C31 C29 111.06(14) . . ? F34 C31 C29 112.46(14) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C24 N1 C2 C3 -161.33(12) . . . . ? C13 N1 C2 C3 76.32(16) . . . . ? N1 C2 C3 N4 67.17(17) . . . . ? C2 C3 N4 C8 -153.34(15) . . . . ? C2 C3 N4 N5 35.3(2) . . . . ? C8 N4 N5 N6 0.63(18) . . . . ? C3 N4 N5 N6 173.32(13) . . . . ? N4 N5 N6 C7 -0.74(17) . . . . ? N5 N6 C7 C8 0.60(19) . . . . ? N5 N6 C7 C9 -176.57(15) . . . . ? N5 N4 C8 C7 -0.25(18) . . . . ? C3 N4 C8 C7 -172.32(15) . . . . ? N6 C7 C8 N4 -0.20(18) . . . . ? C9 C7 C8 N4 176.66(16) . . . . ? N6 C7 C9 F12 -58.6(2) . . . . ? C8 C7 C9 F12 124.86(19) . . . . ? N6 C7 C9 F10 -179.67(15) . . . . ? C8 C7 C9 F10 3.8(3) . . . . ? N6 C7 C9 F11 61.3(2) . . . . ? C8 C7 C9 F11 -115.3(2) . . . . ? C24 N1 C13 C14 75.45(16) . . . . ? C2 N1 C13 C14 -162.47(13) . . . . ? N1 C13 C14 N15 70.66(17) . . . . ? C13 C14 N15 N16 126.26(14) . . . . ? C13 C14 N15 C19 -56.1(2) . . . . ? C19 N15 N16 N17 0.40(17) . . . . ? C14 N15 N16 N17 178.46(13) . . . . ? N15 N16 N17 C18 -0.26(17) . . . . ? N16 N17 C18 C19 0.04(18) . . . . ? N16 N17 C18 C20 -179.65(14) . . . . ? N16 N15 C19 C18 -0.36(17) . . . . ? C14 N15 C19 C18 -178.19(14) . . . . ? N17 C18 C19 N15 0.19(17) . . . . ? C20 C18 C19 N15 179.84(16) . . . . ? N17 C18 C20 F21 177.06(15) . . . . ? C19 C18 C20 F21 -2.6(2) . . . . ? N17 C18 C20 F22 57.1(2) . . . . ? C19 C18 C20 F22 -122.51(19) . . . . ? N17 C18 C20 F23 -63.8(2) . . . . ? C19 C18 C20 F23 116.58(19) . . . . ? C2 N1 C24 C25 79.04(16) . . . . ? C13 N1 C24 C25 -159.20(13) . . . . ? N1 C24 C25 N26 62.76(19) . . . . ? C24 C25 N26 C30 -128.80(17) . . . . ? C24 C25 N26 N27 53.76(19) . . . . ? C30 N26 N27 N28 -0.27(17) . . . . ? C25 N26 N27 N28 177.58(13) . . . . ? N26 N27 N28 C29 0.02(17) . . . . ? N27 N28 C29 C30 0.24(18) . . . . ? N27 N28 C29 C31 -179.06(14) . . . . ? N27 N26 C30 C29 0.40(17) . . . . ? C25 N26 C30 C29 -177.24(14) . . . . ? N28 C29 C30 N26 -0.38(18) . . . . ? C31 C29 C30 N26 178.85(15) . . . . ? N28 C29 C31 F32 83.0(2) . . . . ? C30 C29 C31 F32 -96.1(2) . . . . ? N28 C29 C31 F33 -156.49(15) . . . . ? C30 C29 C31 F33 24.4(2) . . . . ? N28 C29 C31 F34 -37.3(2) . . . . ? C30 C29 C31 F34 143.55(17) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 28.40 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.421 _refine_diff_density_min -0.481 _refine_diff_density_rms 0.053