Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2004 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'ProfD Rudiger Mews' _publ_contact_author_address ; Department of Inorganic and Physical Chemistry University of Bremen PO Box 330440 Bremen D-28334 GERMANY ; _publ_contact_author_email MEWS@CHEMIE.UNI-BREMEN.DE loop_ _publ_author_name _publ_author_address M.Kingston ; Institut fur Anorganische und Physikalisch Chemie der Universitat Postfach 330 440 28334 Bremen Bundesrepublik Deutschland ; S.-J.Chen ; Institut fur Anorganische und Physikalisch Chemie der Universitat Postfach 330 440 28334 Bremen Bundesrepublik Deutschland ; E.Lork ; Institut fur Anorganische und Physikalisch Chemie der Universitat Postfach 330 440 28334 Bremen Bundesrepublik Deutschland ; R.Mews ; Institut fur Anorganische und Physikalisch Chemie der Universitat Postfach 330 440 28334 Bremen Bundesrepublik Deutschland ; _publ_section_title ; Anionic Triazine Systems ; #============================================================================ data_mk9 _database_code_depnum_ccdc_archive 'CCDC 231366' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H18 N3 S, C3 F4 N3' _chemical_formula_sum 'C9 H18 F4 N6 S' _chemical_formula_weight 318.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 9.473(2) _cell_length_b 11.958(2) _cell_length_c 13.066(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1480.1(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 8000 _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 26.25 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.429 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.262 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9255 _exptl_absorpt_correction_T_max 0.9743 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Stoe IPDS' _diffrn_measurement_method 'profile data from psi-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 'random variation +/-2.0' _diffrn_reflns_number 16774 _diffrn_reflns_av_R_equivalents 0.0769 _diffrn_reflns_av_sigmaI/netI 0.0371 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.66 _diffrn_reflns_theta_max 26.13 _reflns_number_total 2895 _reflns_number_gt 2598 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Stoe Expose' _computing_cell_refinement 'Stoe Cell' _computing_data_reduction 'Stoe Reduce' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Diamond _computing_publication_material Shelxl-97 _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^)+(0.0729P)^2^+0.2369P] 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 refU _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 0.00(11) _refine_ls_number_reflns 2895 _refine_ls_number_parameters 188 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0490 _refine_ls_R_factor_gt 0.0428 _refine_ls_wR_factor_ref 0.1195 _refine_ls_wR_factor_gt 0.1130 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _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 0.2103(3) 0.4395(3) 0.3637(2) 0.0536(7) Uani 1 1 d . . . F1 F 0.2001(2) 0.4561(2) 0.25792(15) 0.0795(6) Uani 1 1 d . . . F2 F 0.0783(2) 0.3960(2) 0.3853(2) 0.0890(8) Uani 1 1 d . . . N1 N 0.3111(3) 0.3558(2) 0.3818(2) 0.0573(6) Uani 1 1 d . . . C2 C 0.4065(3) 0.3848(3) 0.4456(2) 0.0491(7) Uani 1 1 d . . . F3 F 0.5046(2) 0.30695(18) 0.46689(17) 0.0733(6) Uani 1 1 d . . . N2 N 0.4293(3) 0.4799(2) 0.4956(2) 0.0519(6) Uani 1 1 d . . . C3 C 0.3284(3) 0.5511(2) 0.4717(2) 0.0485(6) Uani 1 1 d . . . F4 F 0.3412(3) 0.65065(17) 0.51912(18) 0.0750(6) Uani 1 1 d . . . N3 N 0.2219(3) 0.5437(2) 0.4118(2) 0.0540(6) Uani 1 1 d . . . S1 S 0.67440(7) 0.43240(5) 0.26914(5) 0.04162(17) Uani 1 1 d . . . N4 N 0.7697(3) 0.3240(2) 0.24434(19) 0.0498(6) Uani 1 1 d . . . N5 N 0.5990(2) 0.4500(2) 0.15342(19) 0.0491(6) Uani 1 1 d . . . N6 N 0.7578(3) 0.5495(2) 0.2786(2) 0.0543(6) Uani 1 1 d . . . C4 C 0.8725(3) 0.3189(3) 0.1601(3) 0.0542(7) Uani 1 1 d . . . H4A H 0.9629 0.3499 0.1831 0.078(3) Uiso 1 1 calc R . . H4B H 0.8374 0.3625 0.1020 0.078(3) Uiso 1 1 calc R . . H4C H 0.8858 0.2409 0.1392 0.078(3) Uiso 1 1 calc R . . C5 C 0.7994(3) 0.2495(3) 0.3312(3) 0.0591(8) Uani 1 1 d . . . H5A H 0.7981 0.1717 0.3078 0.078(3) Uiso 1 1 calc R . . H5B H 0.7274 0.2601 0.3841 0.078(3) Uiso 1 1 calc R . . H5C H 0.8926 0.2672 0.3595 0.078(3) Uiso 1 1 calc R . . C6 C 0.5145(4) 0.5539(4) 0.1489(3) 0.0675(9) Uani 1 1 d . . . H6A H 0.4706 0.5605 0.0812 0.078(3) Uiso 1 1 calc R . . H6B H 0.5761 0.6185 0.1608 0.078(3) Uiso 1 1 calc R . . H6C H 0.4409 0.5517 0.2016 0.078(3) Uiso 1 1 calc R . . C7 C 0.5117(4) 0.3528(3) 0.1266(3) 0.0627(8) Uani 1 1 d . . . H7A H 0.4394 0.3417 0.1792 0.078(3) Uiso 1 1 calc R . . H7B H 0.5714 0.2860 0.1224 0.078(3) Uiso 1 1 calc R . . H7C H 0.4661 0.3658 0.0603 0.078(3) Uiso 1 1 calc R . . C8 C 0.7854(5) 0.5854(4) 0.3836(3) 0.0774(11) Uani 1 1 d . . . H8A H 0.8819 0.5647 0.4028 0.078(3) Uiso 1 1 calc R . . H8B H 0.7184 0.5489 0.4299 0.078(3) Uiso 1 1 calc R . . H8C H 0.7745 0.6667 0.3884 0.078(3) Uiso 1 1 calc R . . C9 C 0.8537(4) 0.5930(3) 0.2000(3) 0.0649(9) Uani 1 1 d . . . H9A H 0.8522 0.6749 0.2014 0.078(3) Uiso 1 1 calc R . . H9B H 0.8231 0.5667 0.1325 0.078(3) Uiso 1 1 calc R . . H9C H 0.9497 0.5665 0.2137 0.078(3) Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0475(14) 0.0631(18) 0.0503(15) -0.0038(14) -0.0005(11) -0.0092(13) F1 0.0790(14) 0.1045(17) 0.0551(11) -0.0061(10) -0.0090(9) -0.0014(12) F2 0.0584(12) 0.108(2) 0.1005(18) -0.0158(15) 0.0100(11) -0.0271(12) N1 0.0634(15) 0.0465(13) 0.0620(15) -0.0068(11) 0.0109(13) -0.0049(12) C2 0.0543(16) 0.0473(16) 0.0457(14) 0.0099(12) 0.0092(12) 0.0088(12) F3 0.0836(14) 0.0665(14) 0.0699(12) 0.0163(10) 0.0145(11) 0.0304(11) N2 0.0534(13) 0.0559(14) 0.0465(12) 0.0001(11) -0.0025(11) 0.0033(11) C3 0.0588(14) 0.0389(14) 0.0478(13) -0.0037(10) 0.0013(12) -0.0041(13) F4 0.0967(15) 0.0507(11) 0.0776(12) -0.0200(9) -0.0070(12) -0.0062(11) N3 0.0554(13) 0.0478(15) 0.0588(14) -0.0034(11) -0.0070(11) 0.0043(11) S1 0.0426(3) 0.0433(3) 0.0390(3) 0.0009(2) 0.0015(2) 0.0010(3) N4 0.0515(12) 0.0475(13) 0.0504(13) 0.0056(10) 0.0006(10) 0.0076(10) N5 0.0430(11) 0.0576(15) 0.0468(12) 0.0018(10) -0.0026(9) 0.0032(10) N6 0.0547(13) 0.0527(15) 0.0555(13) -0.0078(11) 0.0010(11) -0.0055(11) C4 0.0510(15) 0.0572(18) 0.0543(15) -0.0053(13) 0.0032(13) 0.0082(13) C5 0.0535(18) 0.0552(19) 0.0687(19) 0.0180(14) -0.0010(14) 0.0002(13) C6 0.0602(17) 0.071(2) 0.071(2) 0.0085(18) -0.0097(16) 0.0176(17) C7 0.0565(17) 0.071(2) 0.0602(18) -0.0130(17) -0.0089(15) -0.0004(15) C8 0.087(3) 0.077(3) 0.069(2) -0.0293(18) -0.0059(19) -0.0081(19) C9 0.0566(18) 0.0504(19) 0.088(2) 0.0065(15) 0.0098(16) -0.0075(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 C1 F2 1.383(4) . ? C1 N3 1.400(4) . ? C1 F1 1.400(4) . ? C1 N1 1.403(4) . ? N1 C2 1.277(4) . ? C2 N2 1.329(4) . ? C2 F3 1.345(3) . ? N2 C3 1.319(4) . ? C3 N3 1.279(4) . ? C3 F4 1.348(3) . ? S1 N6 1.612(3) . ? S1 N4 1.613(2) . ? S1 N5 1.685(2) . ? N4 C5 1.469(4) . ? N4 C4 1.471(4) . ? N5 C7 1.469(4) . ? N5 C6 1.479(4) . ? N6 C8 1.461(4) . ? N6 C9 1.466(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 F2 C1 N3 108.3(3) . . ? F2 C1 F1 101.1(2) . . ? N3 C1 F1 108.8(3) . . ? F2 C1 N1 108.3(3) . . ? N3 C1 N1 120.4(3) . . ? F1 C1 N1 108.3(3) . . ? C2 N1 C1 113.5(3) . . ? N1 C2 N2 132.0(3) . . ? N1 C2 F3 115.9(3) . . ? N2 C2 F3 112.2(3) . . ? C3 N2 C2 108.5(3) . . ? N3 C3 N2 132.2(3) . . ? N3 C3 F4 114.4(3) . . ? N2 C3 F4 113.3(3) . . ? C3 N3 C1 113.5(3) . . ? N6 S1 N4 116.04(14) . . ? N6 S1 N5 99.67(14) . . ? N4 S1 N5 99.06(13) . . ? C5 N4 C4 115.2(2) . . ? C5 N4 S1 116.1(2) . . ? C4 N4 S1 123.7(2) . . ? C7 N5 C6 110.5(3) . . ? C7 N5 S1 110.7(2) . . ? C6 N5 S1 111.7(2) . . ? C8 N6 C9 116.2(3) . . ? C8 N6 S1 114.5(3) . . ? C9 N6 S1 123.9(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 F2 C1 N1 C2 -123.8(3) . . . . ? N3 C1 N1 C2 1.5(4) . . . . ? F1 C1 N1 C2 127.4(3) . . . . ? C1 N1 C2 N2 -1.8(5) . . . . ? C1 N1 C2 F3 179.0(2) . . . . ? N1 C2 N2 C3 1.4(5) . . . . ? F3 C2 N2 C3 -179.3(2) . . . . ? C2 N2 C3 N3 -0.8(5) . . . . ? C2 N2 C3 F4 179.6(2) . . . . ? N2 C3 N3 C1 0.8(5) . . . . ? F4 C3 N3 C1 -179.7(3) . . . . ? F2 C1 N3 C3 124.2(3) . . . . ? F1 C1 N3 C3 -126.8(3) . . . . ? N1 C1 N3 C3 -1.0(4) . . . . ? N6 S1 N4 C5 102.9(2) . . . . ? N5 S1 N4 C5 -151.6(2) . . . . ? N6 S1 N4 C4 -50.6(3) . . . . ? N5 S1 N4 C4 54.9(3) . . . . ? N6 S1 N5 C7 -178.8(2) . . . . ? N4 S1 N5 C7 62.6(2) . . . . ? N6 S1 N5 C6 -55.1(2) . . . . ? N4 S1 N5 C6 -173.7(2) . . . . ? N4 S1 N6 C8 -100.0(3) . . . . ? N5 S1 N6 C8 154.8(3) . . . . ? N4 S1 N6 C9 53.1(3) . . . . ? N5 S1 N6 C9 -52.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 26.13 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.281 _refine_diff_density_min -0.232 _refine_diff_density_rms 0.048 data_mk12 _database_code_depnum_ccdc_archive 'CCDC 231367' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H18 N3 S, C3 F2 N3 O' _chemical_formula_sum 'C9 H18 F2 N6 O S' _chemical_formula_weight 296.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 11.513(14) _cell_length_b 9.144(8) _cell_length_c 13.527(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.35(6) _cell_angle_gamma 90.00 _cell_volume 1424(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 46 _cell_measurement_theta_min 2.674 _cell_measurement_theta_max 12.528 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.383 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.253 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.8631 _exptl_absorpt_correction_T_max 0.9512 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens P4' _diffrn_measurement_method '2\q/\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 197 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 'random variation +/-2.0' _diffrn_reflns_number 4227 _diffrn_reflns_av_R_equivalents 0.0452 _diffrn_reflns_av_sigmaI/netI 0.0838 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 1 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.69 _diffrn_reflns_theta_max 27.55 _reflns_number_total 3242 _reflns_number_gt 2038 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens XSCANS' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; 21 reflections with Fo^2 at least 10times Fc^2 were omitted. 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^)+(0.1072P)^2^+0.9153P] 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 refU _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.003(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3242 _refine_ls_number_parameters 180 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1186 _refine_ls_R_factor_gt 0.0706 _refine_ls_wR_factor_ref 0.2135 _refine_ls_wR_factor_gt 0.1858 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4820(4) 0.6022(4) 0.2247(3) 0.0347(9) Uani 1 1 d . . . O1 O 0.5005(3) 0.5831(4) 0.3133(2) 0.0525(9) Uani 1 1 d . . . N1 N 0.4042(3) 0.5129(4) 0.1728(2) 0.0351(8) Uani 1 1 d . . . C2 C 0.3911(4) 0.5469(5) 0.0808(3) 0.0375(9) Uani 1 1 d . . . F1 F 0.3178(2) 0.4596(4) 0.02843(19) 0.0615(8) Uani 1 1 d . . . N2 N 0.4342(3) 0.6528(4) 0.0277(2) 0.0426(9) Uani 1 1 d . . . C3 C 0.5074(4) 0.7289(5) 0.0842(3) 0.0425(10) Uani 1 1 d . . . F2 F 0.5581(3) 0.8393(3) 0.0361(2) 0.0760(10) Uani 1 1 d . . . N3 N 0.5385(3) 0.7140(4) 0.1752(2) 0.0410(8) Uani 1 1 d . . . S1 S 0.51845(9) 0.20469(10) 0.28810(6) 0.0325(3) Uani 1 1 d . . . N4 N 0.5287(3) 0.2204(4) 0.4124(2) 0.0396(8) Uani 1 1 d . . . C4 C 0.4220(4) 0.2836(5) 0.4530(3) 0.0482(11) Uani 1 1 d . . . H4A H 0.4323 0.2965 0.5246 0.059(4) Uiso 1 1 calc R . . H4B H 0.3565 0.2177 0.4394 0.059(4) Uiso 1 1 calc R . . H4C H 0.4065 0.3787 0.4219 0.059(4) Uiso 1 1 calc R . . C5 C 0.6324(5) 0.3089(5) 0.4431(3) 0.0514(12) Uani 1 1 d . . . H5A H 0.6287 0.4047 0.4107 0.059(4) Uiso 1 1 calc R . . H5B H 0.7033 0.2580 0.4238 0.059(4) Uiso 1 1 calc R . . H5C H 0.6334 0.3221 0.5150 0.059(4) Uiso 1 1 calc R . . N5 N 0.6420(3) 0.1271(4) 0.2675(2) 0.0386(8) Uani 1 1 d . . . C6 C 0.6837(4) 0.1441(5) 0.1666(3) 0.0425(10) Uani 1 1 d . . . H6A H 0.7680 0.1583 0.1687 0.059(4) Uiso 1 1 calc R . . H6B H 0.6461 0.2292 0.1355 0.059(4) Uiso 1 1 calc R . . H6C H 0.6646 0.0561 0.1282 0.059(4) Uiso 1 1 calc R . . C7 C 0.6854(4) -0.0028(5) 0.3200(3) 0.0426(10) Uani 1 1 d . . . H7A H 0.6625 -0.0908 0.2830 0.059(4) Uiso 1 1 calc R . . H7B H 0.6524 -0.0062 0.3861 0.059(4) Uiso 1 1 calc R . . H7C H 0.7703 0.0018 0.3260 0.059(4) Uiso 1 1 calc R . . N6 N 0.4053(3) 0.0974(4) 0.2817(2) 0.0385(8) Uani 1 1 d . . . C8 C 0.3454(4) 0.0994(6) 0.1836(3) 0.0504(12) Uani 1 1 d . . . H8A H 0.3817 0.0278 0.1401 0.059(4) Uiso 1 1 calc R . . H8B H 0.3515 0.1972 0.1545 0.059(4) Uiso 1 1 calc R . . H8C H 0.2633 0.0744 0.1912 0.059(4) Uiso 1 1 calc R . . C9 C 0.4039(4) -0.0442(5) 0.3321(3) 0.0427(10) Uani 1 1 d . . . H9A H 0.3246 -0.0834 0.3304 0.059(4) Uiso 1 1 calc R . . H9B H 0.4304 -0.0317 0.4010 0.059(4) Uiso 1 1 calc R . . H9C H 0.4557 -0.1123 0.2987 0.059(4) Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.039(2) 0.038(2) 0.0265(18) -0.0052(16) -0.0038(16) 0.0070(19) O1 0.074(2) 0.060(2) 0.0227(13) 0.0001(13) -0.0126(13) 0.0019(18) N1 0.0383(19) 0.0378(18) 0.0290(15) -0.0014(14) -0.0047(13) -0.0005(15) C2 0.034(2) 0.048(2) 0.0300(18) -0.0049(18) -0.0074(16) 0.0022(19) F1 0.0491(16) 0.093(2) 0.0415(14) -0.0198(14) -0.0113(12) -0.0152(16) N2 0.056(2) 0.047(2) 0.0249(15) 0.0019(15) -0.0036(15) 0.0073(18) C3 0.064(3) 0.032(2) 0.0314(19) 0.0015(16) 0.0106(19) 0.003(2) F2 0.129(3) 0.0442(16) 0.0555(17) 0.0097(13) 0.0230(18) -0.0188(18) N3 0.054(2) 0.0343(19) 0.0344(17) -0.0074(14) 0.0009(15) -0.0065(17) S1 0.0443(6) 0.0284(5) 0.0246(4) 0.0011(4) -0.0055(4) 0.0019(5) N4 0.060(2) 0.0293(17) 0.0286(16) -0.0014(13) -0.0113(15) -0.0001(17) C4 0.069(3) 0.040(2) 0.036(2) -0.0100(18) 0.006(2) -0.001(2) C5 0.075(3) 0.038(2) 0.040(2) -0.0018(19) -0.020(2) -0.004(2) N5 0.049(2) 0.0341(18) 0.0325(16) 0.0051(14) -0.0040(15) 0.0065(16) C6 0.052(3) 0.046(2) 0.0301(19) -0.0026(17) 0.0029(18) -0.006(2) C7 0.043(2) 0.034(2) 0.050(2) 0.0038(18) -0.008(2) 0.0061(19) N6 0.051(2) 0.0375(19) 0.0267(15) -0.0031(14) -0.0024(14) 0.0005(17) C8 0.047(3) 0.071(3) 0.033(2) -0.010(2) -0.0080(18) -0.006(2) C9 0.050(3) 0.035(2) 0.043(2) -0.0013(18) 0.0014(19) -0.005(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.225(4) . ? C1 N1 1.390(5) . ? C1 N3 1.391(5) . ? N1 C2 1.288(5) . ? C2 N2 1.310(6) . ? C2 F1 1.350(5) . ? N2 C3 1.322(6) . ? C3 N3 1.281(5) . ? C3 F2 1.342(5) . ? S1 N5 1.620(4) . ? S1 N6 1.631(4) . ? S1 N4 1.689(3) . ? N4 C4 1.475(6) . ? N4 C5 1.493(6) . ? N5 C6 1.465(5) . ? N5 C7 1.466(5) . ? N6 C9 1.464(5) . ? N6 C8 1.481(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 N1 120.4(4) . . ? O1 C1 N3 120.2(4) . . ? N1 C1 N3 119.4(3) . . ? C2 N1 C1 113.9(3) . . ? N1 C2 N2 132.1(4) . . ? N1 C2 F1 115.0(4) . . ? N2 C2 F1 112.9(3) . . ? C2 N2 C3 108.5(3) . . ? N3 C3 N2 131.2(4) . . ? N3 C3 F2 115.6(4) . . ? N2 C3 F2 113.2(4) . . ? C3 N3 C1 114.7(4) . . ? N5 S1 N6 115.5(2) . . ? N5 S1 N4 99.65(19) . . ? N6 S1 N4 98.11(18) . . ? C4 N4 C5 110.6(3) . . ? C4 N4 S1 111.4(3) . . ? C5 N4 S1 111.1(3) . . ? C6 N5 C7 115.0(4) . . ? C6 N5 S1 115.0(3) . . ? C7 N5 S1 124.2(3) . . ? C9 N6 C8 114.7(4) . . ? C9 N6 S1 121.7(3) . . ? C8 N6 S1 113.3(3) . . ? 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 O1 C1 N1 C2 178.6(4) . . . . ? N3 C1 N1 C2 -1.1(5) . . . . ? C1 N1 C2 N2 -2.8(7) . . . . ? C1 N1 C2 F1 178.7(3) . . . . ? N1 C2 N2 C3 3.5(7) . . . . ? F1 C2 N2 C3 -178.0(4) . . . . ? C2 N2 C3 N3 -0.1(7) . . . . ? C2 N2 C3 F2 179.0(4) . . . . ? N2 C3 N3 C1 -3.1(7) . . . . ? F2 C3 N3 C1 177.9(4) . . . . ? O1 C1 N3 C3 -176.2(4) . . . . ? N1 C1 N3 C3 3.6(6) . . . . ? N5 S1 N4 C4 -177.3(3) . . . . ? N6 S1 N4 C4 -59.6(3) . . . . ? N5 S1 N4 C5 58.9(3) . . . . ? N6 S1 N4 C5 176.7(3) . . . . ? N6 S1 N5 C6 97.8(3) . . . . ? N4 S1 N5 C6 -158.4(3) . . . . ? N6 S1 N5 C7 -53.8(4) . . . . ? N4 S1 N5 C7 50.1(4) . . . . ? N5 S1 N6 C9 48.0(3) . . . . ? N4 S1 N6 C9 -56.8(3) . . . . ? N5 S1 N6 C8 -95.1(3) . . . . ? N4 S1 N6 C8 160.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.55 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.485 _refine_diff_density_min -0.330 _refine_diff_density_rms 0.088 data_mk14 _database_code_depnum_ccdc_archive 'CCDC 231368' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H18 N3 S, C6 F10 N3' _chemical_formula_sum 'C12 H18 F10 N6 S' _chemical_formula_weight 468.38 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/m' _symmetry_space_group_name_Hall '-P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' _cell_length_a 9.1180(10) _cell_length_b 11.388(2) _cell_length_c 9.2320(10) _cell_angle_alpha 90.00 _cell_angle_beta 95.110(10) _cell_angle_gamma 90.00 _cell_volume 954.8(2) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 45 _cell_measurement_theta_min 3.579 _cell_measurement_theta_max 18.185 _exptl_crystal_description blocks _exptl_crystal_colour colorless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.629 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 476 _exptl_absorpt_coefficient_mu 0.275 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.8523 _exptl_absorpt_correction_T_max 0.9220 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens P4' _diffrn_measurement_method '2\q/\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 197 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 'random variation +/-2.0' _diffrn_reflns_number 5179 _diffrn_reflns_av_R_equivalents 0.0334 _diffrn_reflns_av_sigmaI/netI 0.0456 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.85 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2284 _reflns_number_gt 1578 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens XSCANS' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Diamond _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; 6 reflections with Fo^2 more than 10 times bigger than Fc^2 omitted. 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^)+(0.1444P)^2^+0.8904P] 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 refU _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.003(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2284 _refine_ls_number_parameters 153 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1109 _refine_ls_R_factor_gt 0.0813 _refine_ls_wR_factor_ref 0.2504 _refine_ls_wR_factor_gt 0.2249 _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 F1 F 0.1971(3) 0.1333(2) 0.1958(3) 0.0561(7) Uani 1 1 d . . . N3 N -0.1711(5) 0.2500 0.1916(5) 0.0418(11) Uani 1 2 d S . . N1 N 0.0314(5) 0.2500 0.3910(5) 0.0386(10) Uani 1 2 d S . . F2 F -0.0020(3) 0.0440(2) 0.2321(4) 0.0743(10) Uani 1 1 d . . . F3 F 0.0183(3) 0.1313(3) 0.0290(3) 0.0726(9) Uani 1 1 d . . . C4 C -0.2530(6) 0.2500 0.2951(6) 0.0358(11) Uani 1 2 d S . . C1 C -0.0143(5) 0.2500 0.2372(5) 0.0320(10) Uani 1 2 d S . . C3 C -0.0753(7) 0.2500 0.4693(6) 0.0420(12) Uani 1 2 d S . . N2 N -0.2209(5) 0.2500 0.4396(5) 0.0475(12) Uani 1 2 d S . . F4 F -0.0340(5) 0.2500 0.6153(4) 0.0696(12) Uani 1 2 d S . . C5 C -0.4113(6) 0.2500 0.2546(7) 0.0444(13) Uani 1 2 d S . . C2 C 0.0505(5) 0.1393(3) 0.1723(5) 0.0441(9) Uani 1 1 d . . . F5 F -0.4872(5) 0.1623(5) 0.3008(7) 0.137(2) Uani 1 1 d . . . F6 F -0.4527(6) 0.2500 0.1100(7) 0.193(5) Uani 1 2 d S . . S1 S 0.46098(16) 0.2500 0.65608(15) 0.0388(4) Uani 1 2 d S . . N4 N 0.5824(5) 0.2500 0.8031(5) 0.0387(10) Uani 1 2 d S . . N5 N 0.3745(4) 0.1293(3) 0.6864(4) 0.0508(9) Uani 1 1 d . . . C6 C 0.6754(5) 0.1432(4) 0.8130(5) 0.0522(11) Uani 1 1 d . . . H6A H 0.7372 0.1415 0.7315 0.074(6) Uiso 1 1 calc R . . H6B H 0.6124 0.0733 0.8094 0.074(6) Uiso 1 1 calc R . . H6C H 0.7383 0.1440 0.9049 0.074(6) Uiso 1 1 calc R . . C7 C 0.3008(6) 0.0716(4) 0.5588(6) 0.0636(14) Uani 1 1 d . . . H7A H 0.3072 -0.0137 0.5713 0.074(6) Uiso 1 1 calc R . . H7B H 0.3486 0.0945 0.4721 0.074(6) Uiso 1 1 calc R . . H7C H 0.1971 0.0954 0.5473 0.074(6) Uiso 1 1 calc R . . C8 C 0.3109(6) 0.1040(5) 0.8221(6) 0.0704(15) Uani 1 1 d . . . H8A H 0.2098 0.1339 0.8168 0.074(6) Uiso 1 1 calc R . . H8B H 0.3698 0.1421 0.9028 0.074(6) Uiso 1 1 calc R . . H8C H 0.3103 0.0189 0.8381 0.074(6) Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.0362(13) 0.0518(14) 0.0796(17) -0.0110(12) 0.0018(12) 0.0141(11) N3 0.026(2) 0.054(3) 0.045(2) 0.000 -0.0042(18) 0.000 N1 0.030(2) 0.045(2) 0.040(2) 0.000 -0.0060(18) 0.000 F2 0.077(2) 0.0321(13) 0.116(3) -0.0064(14) 0.0169(19) -0.0125(13) F3 0.0674(19) 0.090(2) 0.0583(16) -0.0362(15) -0.0041(14) 0.0118(16) C4 0.031(2) 0.024(2) 0.052(3) 0.000 0.000(2) 0.000 C1 0.023(2) 0.035(2) 0.038(2) 0.000 0.0006(19) 0.000 C3 0.043(3) 0.044(3) 0.038(3) 0.000 0.001(2) 0.000 N2 0.038(3) 0.061(3) 0.044(3) 0.000 0.007(2) 0.000 F4 0.056(2) 0.116(4) 0.0353(17) 0.000 -0.0026(16) 0.000 C5 0.031(3) 0.041(3) 0.065(4) 0.000 0.020(3) 0.000 C2 0.036(2) 0.0392(19) 0.057(2) -0.0076(17) 0.0007(17) 0.0016(16) F5 0.069(3) 0.136(4) 0.199(5) 0.041(4) -0.017(3) -0.030(3) F6 0.049(3) 0.453(17) 0.074(4) 0.000 -0.013(3) 0.000 S1 0.0417(8) 0.0292(6) 0.0444(7) 0.000 -0.0027(5) 0.000 N4 0.032(2) 0.037(2) 0.046(2) 0.000 -0.0066(18) 0.000 N5 0.052(2) 0.0386(17) 0.059(2) -0.0012(15) -0.0105(17) -0.0113(16) C6 0.044(2) 0.042(2) 0.069(3) 0.0092(19) -0.005(2) 0.0069(18) C7 0.074(3) 0.036(2) 0.074(3) -0.002(2) -0.031(3) -0.004(2) C8 0.066(3) 0.066(3) 0.080(3) 0.007(3) 0.009(3) -0.026(3) _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 F1 C2 1.337(5) . ? N3 C4 1.264(7) . ? N3 C1 1.454(6) . ? N1 C3 1.263(7) . ? N1 C1 1.444(6) . ? F2 C2 1.325(5) . ? F3 C2 1.332(5) . ? C4 N2 1.340(7) . ? C4 C5 1.458(8) . ? C1 C2 1.536(5) 4_565 ? C1 C2 1.536(5) . ? C3 N2 1.332(8) . ? C3 F4 1.366(6) . ? C5 F5 1.308(6) . ? C5 F5 1.308(6) 4_565 ? C5 F6 1.355(9) . ? S1 N5 1.621(4) . ? S1 N5 1.621(4) 4_565 ? S1 N4 1.674(4) . ? N4 C6 1.481(5) 4_565 ? N4 C6 1.481(5) . ? N5 C8 1.455(7) . ? N5 C7 1.460(5) . ? 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 C4 N3 C1 114.4(4) . . ? C3 N1 C1 113.2(4) . . ? N3 C4 N2 131.4(5) . . ? N3 C4 C5 116.4(5) . . ? N2 C4 C5 112.3(5) . . ? N1 C1 N3 118.3(4) . . ? N1 C1 C2 107.2(3) . 4_565 ? N3 C1 C2 106.8(3) . 4_565 ? N1 C1 C2 107.2(3) . . ? N3 C1 C2 106.8(3) . . ? C2 C1 C2 110.3(4) 4_565 . ? N1 C3 N2 133.4(5) . . ? N1 C3 F4 114.0(5) . . ? N2 C3 F4 112.6(5) . . ? C3 N2 C4 109.3(5) . . ? F5 C5 F5 99.5(6) . 4_565 ? F5 C5 F6 102.2(5) . . ? F5 C5 F6 102.2(5) 4_565 . ? F5 C5 C4 117.2(4) . . ? F5 C5 C4 117.2(4) 4_565 . ? F6 C5 C4 115.8(5) . . ? F2 C2 F3 107.6(3) . . ? F2 C2 F1 106.4(3) . . ? F3 C2 F1 106.6(4) . . ? F2 C2 C1 110.1(3) . . ? F3 C2 C1 112.6(3) . . ? F1 C2 C1 113.1(3) . . ? N5 S1 N5 115.9(3) . 4_565 ? N5 S1 N4 99.02(16) . . ? N5 S1 N4 99.02(16) 4_565 . ? C6 N4 C6 110.4(5) 4_565 . ? C6 N4 S1 112.6(3) 4_565 . ? C6 N4 S1 112.6(3) . . ? C8 N5 C7 114.5(4) . . ? C8 N5 S1 123.7(3) . . ? C7 N5 S1 116.0(3) . . ? 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 C1 N3 C4 N2 0.0 . . . . ? C1 N3 C4 C5 180.0 . . . . ? C3 N1 C1 N3 0.0 . . . . ? C3 N1 C1 C2 120.8(3) . . . 4_565 ? C3 N1 C1 C2 -120.8(3) . . . . ? C4 N3 C1 N1 0.0 . . . . ? C4 N3 C1 C2 -121.0(3) . . . 4_565 ? C4 N3 C1 C2 121.0(3) . . . . ? C1 N1 C3 N2 0.000(1) . . . . ? C1 N1 C3 F4 180.0 . . . . ? N1 C3 N2 C4 0.000(1) . . . . ? F4 C3 N2 C4 180.0 . . . . ? N3 C4 N2 C3 0.0 . . . . ? C5 C4 N2 C3 180.0 . . . . ? N3 C4 C5 F5 120.9(5) . . . . ? N2 C4 C5 F5 -59.1(5) . . . . ? N3 C4 C5 F5 -120.9(5) . . . 4_565 ? N2 C4 C5 F5 59.1(5) . . . 4_565 ? N3 C4 C5 F6 0.0 . . . . ? N2 C4 C5 F6 180.0 . . . . ? N1 C1 C2 F2 61.5(4) . . . . ? N3 C1 C2 F2 -66.3(4) . . . . ? C2 C1 C2 F2 177.9(2) 4_565 . . . ? N1 C1 C2 F3 -178.4(4) . . . . ? N3 C1 C2 F3 53.7(5) . . . . ? C2 C1 C2 F3 -62.0(5) 4_565 . . . ? N1 C1 C2 F1 -57.4(5) . . . . ? N3 C1 C2 F1 174.7(4) . . . . ? C2 C1 C2 F1 59.0(5) 4_565 . . . ? N5 S1 N4 C6 -176.3(3) . . . 4_565 ? N5 S1 N4 C6 -58.1(4) 4_565 . . 4_565 ? N5 S1 N4 C6 58.1(4) . . . . ? N5 S1 N4 C6 176.3(3) 4_565 . . . ? N5 S1 N5 C8 -52.1(5) 4_565 . . . ? N4 S1 N5 C8 52.6(4) . . . . ? N5 S1 N5 C7 99.5(4) 4_565 . . . ? N4 S1 N5 C7 -155.8(4) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.788 _refine_diff_density_min -0.946 _refine_diff_density_rms 0.104 data_mk18 _database_code_depnum_ccdc_archive 'CCDC 231369' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H18 N3 S, C6 F10 N3' _chemical_formula_sum 'C12 H18 F10 N6 S' _chemical_formula_weight 468.38 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 8.8448(14) _cell_length_b 11.6601(12) _cell_length_c 19.941(2) _cell_angle_alpha 90.00 _cell_angle_beta 102.494(10) _cell_angle_gamma 90.00 _cell_volume 2007.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 36 _cell_measurement_theta_min 2.08 _cell_measurement_theta_max 12.41 _exptl_crystal_description blocks _exptl_crystal_colour colorless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.549 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 952 _exptl_absorpt_coefficient_mu 0.262 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.8588 _exptl_absorpt_correction_T_max 0.9256 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens P4' _diffrn_measurement_method '2\q/\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 197 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 'random variation +/-2.0' _diffrn_reflns_number 3633 _diffrn_reflns_av_R_equivalents 0.0283 _diffrn_reflns_av_sigmaI/netI 0.0461 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 1 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 22.50 _reflns_number_total 2612 _reflns_number_gt 2079 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Diamond _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^)+(0.0397P)^2^+1.8226P] 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 refU _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0050(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2612 _refine_ls_number_parameters 378 _refine_ls_number_restraints 144 _refine_ls_R_factor_all 0.0606 _refine_ls_R_factor_gt 0.0429 _refine_ls_wR_factor_ref 0.1072 _refine_ls_wR_factor_gt 0.0977 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.026 _refine_ls_shift/su_mean 0.004 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 0.3946(3) 0.0514(3) 0.39926(15) 0.0300(7) Uani 1 1 d . . . F1 F 0.3552(2) -0.05416(18) 0.42597(10) 0.0560(6) Uani 1 1 d . . . C2 C 0.5367(4) 0.0310(3) 0.36897(16) 0.0360(8) Uani 1 1 d . . . F2 F 0.65944(19) -0.00158(17) 0.41622(9) 0.0435(5) Uani 1 1 d . . . F3 F 0.5130(2) -0.0485(2) 0.31991(10) 0.0596(6) Uani 1 1 d . . . F4 F 0.5781(2) 0.1272(2) 0.34048(11) 0.0612(6) Uani 1 1 d . . . N1 N 0.4379(3) 0.1356(2) 0.45390(12) 0.0298(6) Uani 1 1 d . . . C3 C 0.3324(3) 0.2126(3) 0.45569(15) 0.0284(7) Uani 1 1 d . . . C4 C 0.3730(3) 0.3001(2) 0.51345(15) 0.0388(9) Uani 1 1 d D . . F5 F 0.5054(12) 0.3511(15) 0.5138(8) 0.077(5) Uani 0.50 1 d PD . . F5A F 0.449(4) 0.380(2) 0.4882(11) 0.088(9) Uani 0.25 1 d PD . . F5B F 0.312(4) 0.3996(14) 0.4918(12) 0.084(13) Uani 0.25 1 d PD . . F6 F 0.2700(17) 0.3820(11) 0.5108(7) 0.048(4) Uani 0.50 1 d PD . . F6A F 0.2591(16) 0.352(3) 0.5339(15) 0.068(11) Uani 0.25 1 d PD . . F6B F 0.311(4) 0.270(2) 0.5651(10) 0.075(9) Uani 0.25 1 d PD . . F7 F 0.387(2) 0.2516(9) 0.5740(4) 0.078(6) Uani 0.50 1 d PD . . F7A F 0.468(4) 0.2626(18) 0.5693(8) 0.110(15) Uani 0.25 1 d PD . . F7B F 0.5202(10) 0.320(3) 0.5397(16) 0.105(14) Uani 0.25 1 d PD . . N2 N 0.1958(3) 0.2302(2) 0.41307(13) 0.0349(7) Uani 1 1 d . . . C5 C 0.1776(3) 0.1597(3) 0.35794(15) 0.0280(7) Uani 1 1 d . . . C6 C 0.0288(3) 0.1802(2) 0.30529(15) 0.0368(8) Uani 1 1 d D . . F8 F -0.0042(19) 0.2892(5) 0.2931(8) 0.053(4) Uani 0.50 1 d PD . . F8A F 0.036(3) 0.2774(10) 0.2726(11) 0.063(8) Uani 0.25 1 d PD . . F8B F 0.042(4) 0.179(3) 0.2408(5) 0.084(12) Uani 0.25 1 d PD . . F9 F 0.0317(15) 0.1338(15) 0.2454(4) 0.054(4) Uani 0.50 1 d PD . . F9A F -0.011(3) 0.1016(16) 0.2574(8) 0.057(8) Uani 0.25 1 d PD . . F9B F -0.071(3) 0.099(2) 0.3107(18) 0.107(13) Uani 0.25 1 d PD . . F10 F -0.0917(12) 0.1353(15) 0.3244(6) 0.081(5) Uani 0.50 1 d PD . . F10A F -0.0892(18) 0.191(2) 0.3352(11) 0.091(13) Uani 0.25 1 d PD . . F10B F -0.040(3) 0.2775(13) 0.3141(13) 0.077(12) Uani 0.25 1 d PD . . N3 N 0.2666(3) 0.0804(2) 0.34333(12) 0.0316(6) Uani 1 1 d . . . S1 S 0.85583(9) 0.26967(7) 0.61996(4) 0.0355(3) Uani 1 1 d . . . N4 N 0.8757(4) 0.4085(2) 0.62472(15) 0.0499(8) Uani 1 1 d . . . C7 C 0.7626(4) 0.4677(3) 0.65637(18) 0.0504(10) Uani 1 1 d . . . H7A H 0.8014 0.4709 0.7062 0.073(3) Uiso 1 1 calc R . . H7B H 0.6641 0.4260 0.6460 0.073(3) Uiso 1 1 calc R . . H7C H 0.7467 0.5458 0.6380 0.073(3) Uiso 1 1 calc R . . C8 C 1.0243(5) 0.4663(3) 0.6316(2) 0.0726(14) Uani 1 1 d . . . H8A H 1.0077 0.5434 0.6116 0.073(3) Uiso 1 1 calc R . . H8B H 1.0904 0.4223 0.6073 0.073(3) Uiso 1 1 calc R . . H8C H 1.0747 0.4723 0.6803 0.073(3) Uiso 1 1 calc R . . N5 N 0.9647(3) 0.1989(3) 0.68128(14) 0.0442(7) Uani 1 1 d . . . C9 C 0.8868(5) 0.1611(3) 0.73557(18) 0.0518(10) Uani 1 1 d . . . H9A H 0.9314 0.0881 0.7547 0.073(3) Uiso 1 1 calc R . . H9B H 0.7760 0.1511 0.7162 0.073(3) Uiso 1 1 calc R . . H9C H 0.9012 0.2190 0.7720 0.073(3) Uiso 1 1 calc R . . C10 C 1.1343(4) 0.2097(4) 0.7010(2) 0.0619(12) Uani 1 1 d . . . H10A H 1.1622 0.2631 0.7397 0.073(3) Uiso 1 1 calc R . . H10B H 1.1735 0.2389 0.6619 0.073(3) Uiso 1 1 calc R . . H10C H 1.1801 0.1344 0.7145 0.073(3) Uiso 1 1 calc R . . N6 N 0.9501(3) 0.2460(2) 0.55675(14) 0.0382(7) Uani 1 1 d . . . C11 C 0.9792(4) 0.1233(3) 0.54446(19) 0.0459(9) Uani 1 1 d . . . H11A H 0.8805 0.0846 0.5260 0.073(3) Uiso 1 1 calc R . . H11B H 1.0300 0.0870 0.5878 0.073(3) Uiso 1 1 calc R . . H11C H 1.0462 0.1171 0.5114 0.073(3) Uiso 1 1 calc R . . C12 C 0.8707(5) 0.3009(3) 0.49168(18) 0.0593(11) Uani 1 1 d . . . H12A H 0.9367 0.2959 0.4581 0.073(3) Uiso 1 1 calc R . . H12B H 0.8505 0.3816 0.5002 0.073(3) Uiso 1 1 calc R . . H12C H 0.7725 0.2615 0.4737 0.073(3) Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0305(17) 0.0255(17) 0.0332(17) -0.0002(14) 0.0053(14) 0.0007(14) F1 0.0565(13) 0.0476(13) 0.0616(13) 0.0020(11) 0.0082(11) -0.0033(11) C2 0.0335(18) 0.043(2) 0.0306(18) 0.0007(17) 0.0057(15) 0.0080(17) F2 0.0293(10) 0.0583(13) 0.0416(11) -0.0003(9) 0.0044(9) 0.0124(9) F3 0.0509(13) 0.0826(16) 0.0443(12) -0.0228(12) 0.0082(10) 0.0199(12) F4 0.0513(13) 0.0732(16) 0.0652(14) 0.0285(13) 0.0263(11) 0.0055(11) N1 0.0290(14) 0.0280(14) 0.0310(14) -0.0035(12) 0.0033(11) 0.0022(12) C3 0.0299(18) 0.0281(17) 0.0290(17) 0.0016(14) 0.0105(14) -0.0033(15) C4 0.038(2) 0.033(2) 0.043(2) -0.0045(18) 0.0033(19) 0.0041(19) F5 0.037(5) 0.109(8) 0.083(10) -0.068(7) 0.010(6) -0.036(6) F5A 0.11(2) 0.072(13) 0.084(14) -0.026(9) 0.015(13) -0.067(15) F5B 0.16(3) 0.040(8) 0.035(11) -0.009(6) -0.004(13) 0.031(14) F6 0.069(5) 0.050(5) 0.023(8) -0.013(4) 0.006(4) 0.032(4) F6A 0.037(6) 0.13(3) 0.033(15) -0.038(14) 0.005(7) 0.009(11) F6B 0.14(2) 0.060(15) 0.044(12) -0.013(9) 0.052(16) -0.027(15) F7 0.146(16) 0.047(4) 0.028(5) -0.002(3) -0.006(6) 0.035(8) F7A 0.13(3) 0.077(16) 0.08(2) -0.054(13) -0.077(18) 0.051(15) F7B 0.041(9) 0.18(3) 0.08(2) -0.082(19) -0.010(10) 0.029(15) N2 0.0293(15) 0.0399(16) 0.0335(15) -0.0051(13) 0.0025(12) 0.0083(13) C5 0.0259(17) 0.0290(17) 0.0295(17) 0.0037(15) 0.0068(14) -0.0019(15) C6 0.033(2) 0.039(2) 0.038(2) -0.0018(19) 0.0061(16) 0.0047(18) F8 0.062(8) 0.036(4) 0.048(8) -0.008(3) -0.016(6) 0.017(4) F8A 0.074(12) 0.046(11) 0.062(15) 0.028(11) 0.001(8) 0.014(7) F8B 0.086(12) 0.13(3) 0.035(8) 0.018(10) 0.015(7) 0.070(16) F9 0.053(8) 0.053(9) 0.041(4) -0.016(5) -0.022(4) 0.025(6) F9A 0.034(12) 0.045(9) 0.075(13) -0.013(9) -0.026(8) -0.006(7) F9B 0.021(8) 0.061(10) 0.22(3) 0.060(14) -0.013(12) -0.010(8) F10 0.032(6) 0.129(14) 0.076(10) 0.053(8) -0.001(5) -0.015(7) F10A 0.014(7) 0.21(4) 0.043(8) -0.001(18) 0.003(5) 0.011(14) F10B 0.072(19) 0.077(13) 0.064(18) -0.025(11) -0.026(13) 0.060(14) N3 0.0295(14) 0.0331(15) 0.0298(14) -0.0010(12) 0.0009(12) 0.0050(13) S1 0.0359(5) 0.0320(5) 0.0411(5) -0.0082(4) 0.0139(4) -0.0029(4) N4 0.067(2) 0.0321(17) 0.0595(19) -0.0093(14) 0.0340(17) -0.0006(15) C7 0.069(3) 0.039(2) 0.046(2) -0.0061(18) 0.0183(19) 0.0157(19) C8 0.100(4) 0.043(2) 0.094(3) -0.021(2) 0.063(3) -0.026(2) N5 0.0415(17) 0.0496(19) 0.0423(16) -0.0011(14) 0.0109(14) -0.0059(14) C9 0.068(3) 0.043(2) 0.050(2) -0.0019(18) 0.025(2) -0.009(2) C10 0.039(2) 0.087(3) 0.056(2) -0.012(2) 0.0028(19) 0.005(2) N6 0.0447(17) 0.0324(16) 0.0422(16) -0.0079(13) 0.0195(13) -0.0012(13) C11 0.044(2) 0.038(2) 0.059(2) -0.0168(18) 0.0206(18) -0.0002(17) C12 0.078(3) 0.061(3) 0.046(2) 0.000(2) 0.026(2) 0.019(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 F1 1.414(4) . ? C1 N3 1.447(4) . ? C1 N1 1.456(4) . ? C1 C2 1.526(4) . ? C2 F2 1.330(3) . ? C2 F3 1.331(4) . ? C2 F4 1.344(4) . ? N1 C3 1.300(4) . ? C3 N2 1.334(4) . ? C3 C4 1.522(4) . ? C4 F5 1.312(5) . ? C4 F6A 1.313(5) . ? C4 F7B 1.313(5) . ? C4 F5B 1.313(5) . ? C4 F7A 1.314(5) . ? C4 F6 1.314(5) . ? C4 F6B 1.314(5) . ? C4 F7 1.314(5) . ? C4 F5A 1.314(5) . ? N2 C5 1.354(4) . ? C5 N3 1.288(4) . ? C5 C6 1.514(4) . ? C6 F8 1.315(5) . ? C6 F9A 1.315(5) . ? C6 F9B 1.315(5) . ? C6 F10A 1.316(5) . ? C6 F8A 1.316(5) . ? C6 F8B 1.316(5) . ? C6 F10B 1.316(5) . ? C6 F9 1.316(5) . ? C6 F10 1.316(5) . ? S1 N5 1.610(3) . ? S1 N4 1.628(3) . ? S1 N6 1.678(3) . ? N4 C8 1.457(5) . ? N4 C7 1.466(4) . ? N5 C9 1.471(4) . ? N5 C10 1.472(4) . ? N6 C12 1.480(4) . ? N6 C11 1.484(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 F1 C1 N3 106.2(2) . . ? F1 C1 N1 110.6(2) . . ? N3 C1 N1 117.0(2) . . ? F1 C1 C2 107.8(2) . . ? N3 C1 C2 107.8(2) . . ? N1 C1 C2 107.2(2) . . ? F2 C2 F3 107.2(3) . . ? F2 C2 F4 106.4(3) . . ? F3 C2 F4 106.5(3) . . ? F2 C2 C1 112.3(2) . . ? F3 C2 C1 112.8(3) . . ? F4 C2 C1 111.2(3) . . ? C3 N1 C1 114.4(2) . . ? N1 C3 N2 130.1(3) . . ? N1 C3 C4 115.5(3) . . ? N2 C3 C4 114.3(3) . . ? F5 C4 F6 106.3(3) . . ? F5 C4 F7 106.3(3) . . ? F6 C4 F7 106.2(3) . . ? F5 C4 C3 111.8(7) . . ? F6 C4 C3 114.1(7) . . ? F7 C4 C3 111.5(6) . . ? F5 F5A C4 74.0(6) . . ? C3 N2 C5 110.9(2) . . ? N3 C5 N2 130.4(3) . . ? N3 C5 C6 116.0(3) . . ? N2 C5 C6 113.6(2) . . ? F8 C6 F9 106.0(3) . . ? F8 C6 F10 106.1(3) . . ? F9 C6 F10 106.0(3) . . ? F8 C6 C5 113.9(7) . . ? F9 C6 C5 112.3(6) . . ? F10 C6 C5 111.9(6) . . ? C5 N3 C1 114.1(2) . . ? N5 S1 N4 115.19(16) . . ? N5 S1 N6 100.01(14) . . ? N4 S1 N6 98.17(14) . . ? C8 N4 C7 115.3(3) . . ? C8 N4 S1 123.3(3) . . ? C7 N4 S1 114.7(2) . . ? C9 N5 C10 116.2(3) . . ? C9 N5 S1 114.5(2) . . ? C10 N5 S1 124.5(3) . . ? C12 N6 C11 109.8(3) . . ? C12 N6 S1 111.7(2) . . ? C11 N6 S1 114.5(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 F1 C1 C2 F2 -62.9(3) . . . . ? N3 C1 C2 F2 -177.1(2) . . . . ? N1 C1 C2 F2 56.2(3) . . . . ? F1 C1 C2 F3 58.4(3) . . . . ? N3 C1 C2 F3 -55.8(3) . . . . ? N1 C1 C2 F3 177.5(2) . . . . ? F1 C1 C2 F4 178.0(2) . . . . ? N3 C1 C2 F4 63.8(3) . . . . ? N1 C1 C2 F4 -62.9(3) . . . . ? F1 C1 N1 C3 -104.2(3) . . . . ? N3 C1 N1 C3 17.5(4) . . . . ? C2 C1 N1 C3 138.6(3) . . . . ? C1 N1 C3 N2 -4.5(5) . . . . ? C1 N1 C3 C4 178.5(2) . . . . ? N1 C3 C4 F5 54.1(10) . . . . ? N2 C3 C4 F5 -123.3(10) . . . . ? N1 C3 C4 F6 174.9(9) . . . . ? N2 C3 C4 F6 -2.6(10) . . . . ? N1 C3 C4 F7 -64.8(9) . . . . ? N2 C3 C4 F7 117.8(9) . . . . ? N1 C3 N2 C5 -5.7(4) . . . . ? C4 C3 N2 C5 171.2(2) . . . . ? C3 N2 C5 N3 2.5(5) . . . . ? C3 N2 C5 C6 -176.5(2) . . . . ? N3 C5 C6 F8 -136.5(10) . . . . ? N2 C5 C6 F8 42.7(10) . . . . ? N3 C5 C6 F9 -15.9(9) . . . . ? N2 C5 C6 F9 163.2(9) . . . . ? N3 C5 C6 F10 103.1(10) . . . . ? N2 C5 C6 F10 -77.7(10) . . . . ? N2 C5 N3 C1 10.2(5) . . . . ? C6 C5 N3 C1 -170.8(2) . . . . ? F1 C1 N3 C5 104.1(3) . . . . ? N1 C1 N3 C5 -19.9(4) . . . . ? C2 C1 N3 C5 -140.7(3) . . . . ? N5 S1 N4 C8 53.8(4) . . . . ? N6 S1 N4 C8 -51.4(3) . . . . ? N5 S1 N4 C7 -96.1(3) . . . . ? N6 S1 N4 C7 158.7(3) . . . . ? N4 S1 N5 C9 99.8(3) . . . . ? N6 S1 N5 C9 -156.1(2) . . . . ? N4 S1 N5 C10 -54.5(3) . . . . ? N6 S1 N5 C10 49.5(3) . . . . ? N5 S1 N6 C12 178.7(3) . . . . ? N4 S1 N6 C12 -63.8(3) . . . . ? N5 S1 N6 C11 53.2(3) . . . . ? N4 S1 N6 C11 170.7(2) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 22.50 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.418 _refine_diff_density_min -0.358 _refine_diff_density_rms 0.047 #_eof # End of Crystallographic Information File