# Electronic Supplementary Material (ESI) for Organic and Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Chinmay Chowdhury' _publ_contact_author_email chinmay@iicb.res.in _publ_section_title ; A rapid and facile method for the general synthesis of 3-aryl substituted 4,5,6,7-tetrahydro [1,2,3]triazolo[1,5-a]pyrazines and their ring fused analogues ; loop_ _publ_author_name C.Chowdhury S.ukherjee B.Chakraborty B.Achari # Attachment 'product-3cj.cif.cif' data_snj_2_232 _database_code_depnum_ccdc_archive 'CCDC 804536' #TrackingRef 'product-3cj.cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Triazolo-pyrazine _chemical_melting_point 214-216 _chemical_formula_moiety C23H25F1N4O2S1 _chemical_formula_sum 'C23 H25 F N4 O2 S' _chemical_formula_weight 440.53 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 P21/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 11.4682(11) _cell_length_b 19.7219(18) _cell_length_c 9.6293(9) _cell_angle_alpha 90.00 _cell_angle_beta 103.607(5) _cell_angle_gamma 90.00 _cell_volume 2116.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3724 _cell_measurement_theta_min 1.83 _cell_measurement_theta_max 24.99 _exptl_crystal_description niddle-shaped _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.382 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 928 _exptl_absorpt_coefficient_mu 0.190 _exptl_absorpt_correction_type None _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 Kappa Apex 2' _diffrn_measurement_method FastFourierTransform _diffrn_detector_area_resol_mean 512x512 _diffrn_standards_number 19 _diffrn_standards_interval_count 9302190 _diffrn_standards_interval_time 10sec _diffrn_standards_decay_% 0 _diffrn_reflns_number 20516 _diffrn_reflns_av_R_equivalents 0.0536 _diffrn_reflns_av_sigmaI/netI 0.0349 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 24.99 _reflns_number_total 3724 _reflns_number_gt 3111 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Apex 2, Bruker Kappa' _computing_cell_refinement 'Apex 2, Bruker Kappa' _computing_data_reduction 'Apex 2, Bruker Kappa' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.3132P] 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 SHELXL _refine_ls_extinction_coef 0.0046(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3724 _refine_ls_number_parameters 282 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0511 _refine_ls_R_factor_gt 0.0423 _refine_ls_wR_factor_ref 0.1436 _refine_ls_wR_factor_gt 0.1308 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _refine_ls_shift/su_max 0.003 _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 S1 S 0.31480(5) 0.40622(2) 0.44940(5) 0.0453(2) Uani 1 1 d . . . N3 N 0.20148(13) 0.54568(7) 0.17626(15) 0.0396(4) Uani 1 1 d . . . N2 N 0.23382(15) 0.56829(9) 0.05849(17) 0.0485(4) Uani 1 1 d . . . N1 N 0.20263(15) 0.52123(8) -0.03909(17) 0.0485(4) Uani 1 1 d . . . N4 N 0.21404(14) 0.46591(8) 0.40618(15) 0.0420(4) Uani 1 1 d . . . O1 O 0.25371(15) 0.34675(7) 0.47717(16) 0.0604(4) Uani 1 1 d . . . O2 O 0.40852(14) 0.43388(8) 0.55910(15) 0.0625(4) Uani 1 1 d . . . F1 F 0.02181(15) 0.22519(7) -0.27084(15) 0.0764(4) Uani 1 1 d . . . C4 C 0.11012(16) 0.40709(9) -0.06696(18) 0.0391(4) Uani 1 1 d . . . C9 C 0.11679(17) 0.45252(10) 0.27928(19) 0.0423(4) Uani 1 1 d . . . H9A H 0.0419 0.4710 0.2929 0.051 Uiso 1 1 calc R . . H9B H 0.1068 0.4040 0.2640 0.051 Uiso 1 1 calc R . . C7 C 0.14955(15) 0.46874(9) 0.01449(18) 0.0391(4) Uani 1 1 d . . . C8 C 0.14832(15) 0.48482(9) 0.15368(18) 0.0372(4) Uani 1 1 d . . . C3 C 0.03172(17) 0.36268(10) -0.02480(19) 0.0438(4) Uani 1 1 d . . . H3 H -0.0017 0.3744 0.0510 0.053 Uiso 1 1 calc R . . C17 C 0.36965(16) 0.38865(9) 0.29778(19) 0.0408(4) Uani 1 1 d . . . C10 C 0.24611(19) 0.53799(10) 0.43898(19) 0.0452(5) Uani 1 1 d . . . H10 H 0.3335 0.5405 0.4729 0.054 Uiso 1 1 calc R . . C11 C 0.20954(18) 0.58503(9) 0.30736(19) 0.0428(4) Uani 1 1 d . . . H11 H 0.1296 0.6031 0.3054 0.051 Uiso 1 1 calc R . . C18 C 0.33676(18) 0.32970(10) 0.2228(2) 0.0492(5) Uani 1 1 d . . . H18 H 0.2884 0.2984 0.2547 0.059 Uiso 1 1 calc R . . C2 C 0.00233(19) 0.30164(10) -0.0927(2) 0.0505(5) Uani 1 1 d . . . H2 H -0.0492 0.2716 -0.0624 0.061 Uiso 1 1 calc R . . C5 C 0.15419(19) 0.38966(11) -0.1855(2) 0.0494(5) Uani 1 1 d . . . H5 H 0.2048 0.4195 -0.2177 0.059 Uiso 1 1 calc R . . C1 C 0.0503(2) 0.28603(10) -0.2054(2) 0.0514(5) Uani 1 1 d . . . C6 C 0.1239(2) 0.32899(12) -0.2554(2) 0.0562(5) Uani 1 1 d . . . H6 H 0.1530 0.3176 -0.3347 0.067 Uiso 1 1 calc R . . C12 C 0.2943(2) 0.64450(10) 0.3140(2) 0.0543(5) Uani 1 1 d . . . H12A H 0.2793 0.6655 0.2204 0.065 Uiso 1 1 calc R . . H12B H 0.3760 0.6275 0.3361 0.065 Uiso 1 1 calc R . . C21 C 0.48074(18) 0.42184(12) 0.1290(2) 0.0544(5) Uani 1 1 d . . . H21 H 0.5298 0.4530 0.0976 0.065 Uiso 1 1 calc R . . C20 C 0.44739(18) 0.36275(12) 0.0509(2) 0.0533(5) Uani 1 1 d . . . C16 C 0.1919(3) 0.55951(12) 0.5612(2) 0.0672(7) Uani 1 1 d . . . H16A H 0.1092 0.5443 0.5394 0.081 Uiso 1 1 calc R . . H16B H 0.2337 0.5352 0.6460 0.081 Uiso 1 1 calc R . . C19 C 0.37557(19) 0.31705(11) 0.1002(2) 0.0550(5) Uani 1 1 d . . . H19 H 0.3529 0.2771 0.0499 0.066 Uiso 1 1 calc R . . C23 C 0.4867(2) 0.35012(15) -0.0849(3) 0.0756(7) Uani 1 1 d . . . H23A H 0.4625 0.3054 -0.1196 0.113 Uiso 1 1 calc R . . H23B H 0.5725 0.3538 -0.0667 0.113 Uiso 1 1 calc R . . H23C H 0.4505 0.3831 -0.1553 0.113 Uiso 1 1 calc R . . C15 C 0.1929(3) 0.63389(13) 0.5987(3) 0.0803(8) Uani 1 1 d . . . H15A H 0.1182 0.6535 0.5452 0.096 Uiso 1 1 calc R . . H15B H 0.1928 0.6374 0.6992 0.096 Uiso 1 1 calc R . . C13 C 0.2839(3) 0.69879(13) 0.4240(3) 0.0768(7) Uani 1 1 d . . . H13A H 0.3458 0.7324 0.4248 0.092 Uiso 1 1 calc R . . H13B H 0.2072 0.7214 0.3910 0.092 Uiso 1 1 calc R . . C14 C 0.2933(3) 0.67683(13) 0.5732(3) 0.0795(8) Uani 1 1 d . . . H14A H 0.2990 0.7170 0.6326 0.095 Uiso 1 1 calc R . . H14B H 0.3676 0.6518 0.6049 0.095 Uiso 1 1 calc R . . C22 C 0.44288(17) 0.43532(10) 0.2516(2) 0.0481(5) Uani 1 1 d . . . H22 H 0.4660 0.4751 0.3027 0.058 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 S1 0.0650(4) 0.0358(3) 0.0335(3) 0.00393(18) 0.0085(2) 0.0045(2) N3 0.0486(9) 0.0357(8) 0.0355(8) 0.0020(6) 0.0123(6) -0.0001(6) N2 0.0630(10) 0.0420(9) 0.0437(9) 0.0044(7) 0.0188(8) -0.0052(8) N1 0.0624(10) 0.0458(10) 0.0405(9) 0.0035(7) 0.0183(7) -0.0049(8) N4 0.0556(9) 0.0366(9) 0.0334(8) -0.0011(6) 0.0096(7) 0.0004(7) O1 0.0957(11) 0.0407(8) 0.0520(8) 0.0107(6) 0.0315(8) 0.0021(7) O2 0.0793(10) 0.0552(9) 0.0420(8) -0.0031(7) -0.0074(7) 0.0123(8) F1 0.1162(11) 0.0532(8) 0.0591(8) -0.0202(6) 0.0188(8) -0.0029(7) C4 0.0441(10) 0.0415(10) 0.0306(9) 0.0027(7) 0.0067(7) 0.0062(8) C9 0.0494(10) 0.0424(10) 0.0363(9) 0.0011(8) 0.0128(8) -0.0036(8) C7 0.0411(9) 0.0417(10) 0.0348(9) 0.0040(8) 0.0093(7) 0.0020(8) C8 0.0391(9) 0.0364(10) 0.0359(9) 0.0013(7) 0.0082(7) -0.0001(7) C3 0.0529(11) 0.0463(11) 0.0328(9) -0.0009(8) 0.0109(8) -0.0005(8) C17 0.0470(10) 0.0355(9) 0.0385(9) 0.0032(8) 0.0076(8) 0.0047(8) C10 0.0604(12) 0.0363(10) 0.0380(10) -0.0028(8) 0.0098(8) 0.0039(8) C11 0.0525(11) 0.0371(10) 0.0390(10) -0.0018(8) 0.0109(8) 0.0029(8) C18 0.0582(12) 0.0389(11) 0.0528(11) -0.0030(9) 0.0176(9) -0.0053(9) C2 0.0651(12) 0.0465(11) 0.0394(10) 0.0020(8) 0.0115(9) -0.0075(9) C5 0.0577(12) 0.0546(12) 0.0397(10) 0.0021(9) 0.0192(9) 0.0008(9) C1 0.0729(13) 0.0405(11) 0.0381(10) -0.0058(8) 0.0073(9) 0.0051(9) C6 0.0716(13) 0.0611(14) 0.0389(10) -0.0059(10) 0.0188(10) 0.0105(11) C12 0.0678(13) 0.0403(11) 0.0537(12) -0.0001(9) 0.0122(10) -0.0058(9) C21 0.0495(11) 0.0567(13) 0.0585(13) 0.0127(10) 0.0157(10) -0.0029(9) C20 0.0504(11) 0.0612(13) 0.0496(11) 0.0038(10) 0.0141(9) 0.0066(10) C16 0.1046(19) 0.0542(14) 0.0490(13) -0.0086(10) 0.0302(13) 0.0036(12) C19 0.0624(12) 0.0496(12) 0.0557(12) -0.0121(10) 0.0194(10) -0.0012(10) C23 0.0751(16) 0.097(2) 0.0627(15) -0.0021(14) 0.0318(13) 0.0056(14) C15 0.122(2) 0.0554(15) 0.0728(16) -0.0163(13) 0.0413(16) 0.0115(15) C13 0.1054(19) 0.0469(14) 0.0734(16) -0.0119(12) 0.0113(14) -0.0098(13) C14 0.114(2) 0.0548(15) 0.0662(16) -0.0205(12) 0.0144(15) 0.0058(15) C22 0.0511(11) 0.0393(11) 0.0513(11) 0.0026(9) 0.0067(9) -0.0027(9) _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 S1 O1 1.4234(15) . ? S1 O2 1.4264(15) . ? S1 N4 1.6333(16) . ? S1 C17 1.7549(19) . ? N3 C8 1.341(2) . ? N3 N2 1.349(2) . ? N3 C11 1.466(2) . ? N2 N1 1.309(2) . ? N1 C7 1.362(2) . ? N4 C9 1.472(2) . ? N4 C10 1.484(2) . ? F1 C1 1.359(2) . ? C4 C3 1.383(3) . ? C4 C5 1.395(3) . ? C4 C7 1.460(3) . ? C9 C8 1.485(2) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C7 C8 1.381(2) . ? C3 C2 1.373(3) . ? C3 H3 0.9300 . ? C17 C18 1.374(3) . ? C17 C22 1.388(3) . ? C10 C16 1.515(3) . ? C10 C11 1.547(3) . ? C10 H10 0.9800 . ? C11 C12 1.515(3) . ? C11 H11 0.9800 . ? C18 C19 1.379(3) . ? C18 H18 0.9300 . ? C2 C1 1.362(3) . ? C2 H2 0.9300 . ? C5 C6 1.377(3) . ? C5 H5 0.9300 . ? C1 C6 1.362(3) . ? C6 H6 0.9300 . ? C12 C13 1.530(3) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C21 C22 1.376(3) . ? C21 C20 1.391(3) . ? C21 H21 0.9300 . ? C20 C19 1.378(3) . ? C20 C23 1.502(3) . ? C16 C15 1.510(3) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C19 H19 0.9300 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C15 C14 1.496(4) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C13 C14 1.480(4) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C22 H22 0.9300 . ? 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 S1 O2 119.64(9) . . ? O1 S1 N4 106.96(9) . . ? O2 S1 N4 106.12(8) . . ? O1 S1 C17 106.39(9) . . ? O2 S1 C17 109.66(10) . . ? N4 S1 C17 107.51(8) . . ? C8 N3 N2 111.34(15) . . ? C8 N3 C11 123.21(15) . . ? N2 N3 C11 125.08(15) . . ? N1 N2 N3 106.64(15) . . ? N2 N1 C7 109.74(15) . . ? C9 N4 C10 116.75(14) . . ? C9 N4 S1 115.77(12) . . ? C10 N4 S1 120.74(13) . . ? C3 C4 C5 118.01(18) . . ? C3 C4 C7 120.69(16) . . ? C5 C4 C7 121.24(17) . . ? N4 C9 C8 108.49(15) . . ? N4 C9 H9A 110.0 . . ? C8 C9 H9A 110.0 . . ? N4 C9 H9B 110.0 . . ? C8 C9 H9B 110.0 . . ? H9A C9 H9B 108.4 . . ? N1 C7 C8 107.50(16) . . ? N1 C7 C4 122.61(16) . . ? C8 C7 C4 129.81(17) . . ? N3 C8 C7 104.77(15) . . ? N3 C8 C9 116.14(15) . . ? C7 C8 C9 138.79(17) . . ? C2 C3 C4 121.28(18) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? C18 C17 C22 120.34(18) . . ? C18 C17 S1 119.77(15) . . ? C22 C17 S1 119.86(15) . . ? N4 C10 C16 107.90(17) . . ? N4 C10 C11 113.23(15) . . ? C16 C10 C11 112.76(17) . . ? N4 C10 H10 107.6 . . ? C16 C10 H10 107.6 . . ? C11 C10 H10 107.6 . . ? N3 C11 C12 110.86(16) . . ? N3 C11 C10 109.76(15) . . ? C12 C11 C10 112.46(16) . . ? N3 C11 H11 107.9 . . ? C12 C11 H11 107.9 . . ? C10 C11 H11 107.9 . . ? C17 C18 C19 119.94(19) . . ? C17 C18 H18 120.0 . . ? C19 C18 H18 120.0 . . ? C1 C2 C3 118.52(19) . . ? C1 C2 H2 120.7 . . ? C3 C2 H2 120.7 . . ? C6 C5 C4 121.04(19) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? F1 C1 C6 119.11(18) . . ? F1 C1 C2 118.1(2) . . ? C6 C1 C2 122.76(19) . . ? C1 C6 C5 118.29(19) . . ? C1 C6 H6 120.9 . . ? C5 C6 H6 120.9 . . ? C11 C12 C13 114.66(19) . . ? C11 C12 H12A 108.6 . . ? C13 C12 H12A 108.6 . . ? C11 C12 H12B 108.6 . . ? C13 C12 H12B 108.6 . . ? H12A C12 H12B 107.6 . . ? C22 C21 C20 121.56(19) . . ? C22 C21 H21 119.2 . . ? C20 C21 H21 119.2 . . ? C19 C20 C21 118.21(19) . . ? C19 C20 C23 121.2(2) . . ? C21 C20 C23 120.6(2) . . ? C15 C16 C10 118.4(2) . . ? C15 C16 H16A 107.7 . . ? C10 C16 H16A 107.7 . . ? C15 C16 H16B 107.7 . . ? C10 C16 H16B 107.7 . . ? H16A C16 H16B 107.1 . . ? C20 C19 C18 121.0(2) . . ? C20 C19 H19 119.5 . . ? C18 C19 H19 119.5 . . ? C20 C23 H23A 109.5 . . ? C20 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C20 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C14 C15 C16 118.3(2) . . ? C14 C15 H15A 107.7 . . ? C16 C15 H15A 107.7 . . ? C14 C15 H15B 107.7 . . ? C16 C15 H15B 107.7 . . ? H15A C15 H15B 107.1 . . ? C14 C13 C12 117.9(2) . . ? C14 C13 H13A 107.8 . . ? C12 C13 H13A 107.8 . . ? C14 C13 H13B 107.8 . . ? C12 C13 H13B 107.8 . . ? H13A C13 H13B 107.2 . . ? C13 C14 C15 116.2(2) . . ? C13 C14 H14A 108.2 . . ? C15 C14 H14A 108.2 . . ? C13 C14 H14B 108.2 . . ? C15 C14 H14B 108.2 . . ? H14A C14 H14B 107.4 . . ? C21 C22 C17 118.91(19) . . ? C21 C22 H22 120.5 . . ? C17 C22 H22 120.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.346 _refine_diff_density_min -0.304 _refine_diff_density_rms 0.044 # Attachment 'product-2--i.cif.cif' data_snj40a_0m _database_code_depnum_ccdc_archive 'CCDC 804692' #TrackingRef 'product-2--i.cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Triazolo-pyrazine _chemical_melting_point 190-191 _chemical_formula_moiety C18H15F3N4 _chemical_formula_sum 'C18 H15 F3 N4' _chemical_formula_weight 344.34 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 P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.9258(4) _cell_length_b 16.4316(8) _cell_length_c 12.9933(6) _cell_angle_alpha 90.00 _cell_angle_beta 105.595(2) _cell_angle_gamma 90.00 _cell_volume 1629.87(14) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 10061 _cell_measurement_theta_min 1.63 _cell_measurement_theta_max 31.00 _exptl_crystal_description Niddle-shaped _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.403 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 0.110 _exptl_absorpt_correction_type None _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 Kappa Apex 2' _diffrn_measurement_method 'Difference Vectors' _diffrn_detector_area_resol_mean 512x512 _diffrn_standards_number 19 _diffrn_standards_interval_count 9049502 _diffrn_standards_interval_time 10sec _diffrn_standards_decay_% 0 _diffrn_reflns_number 33684 _diffrn_reflns_av_R_equivalents 0.0310 _diffrn_reflns_av_sigmaI/netI 0.0353 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 31.00 _reflns_number_total 10061 _reflns_number_gt 7021 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Apex 2, Bruker Kappa' _computing_cell_refinement 'Apex 2, Bruker Kappa' _computing_data_reduction 'Apex 2, Bruker Kappa' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.6606P] 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 SHELXL _refine_ls_extinction_coef 0.011(2) _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 1.4(14) _refine_ls_number_reflns 10061 _refine_ls_number_parameters 452 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1039 _refine_ls_R_factor_gt 0.0783 _refine_ls_wR_factor_ref 0.2271 _refine_ls_wR_factor_gt 0.2102 _refine_ls_goodness_of_fit_ref 1.109 _refine_ls_restrained_S_all 1.109 _refine_ls_shift/su_max 0.020 _refine_ls_shift/su_mean 0.013 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 C12 C 0.7616(4) 0.20573(18) 0.7974(2) 0.0406(6) Uani 1 1 d . . . C7 C 0.4392(4) 0.26600(18) 1.0953(2) 0.0401(6) Uani 1 1 d . . . H7 H 0.3640 0.2276 1.0459 0.048 Uiso 1 1 calc R . . C15 C 0.7663(5) 0.2037(2) 0.5841(3) 0.0489(7) Uani 1 1 d . . . C11 C 0.7569(4) 0.20293(18) 0.9097(2) 0.0404(6) Uani 1 1 d . . . C8 C 0.6130(4) 0.2252(2) 1.1464(2) 0.0461(7) Uani 1 1 d . . . H8A H 0.6861 0.2605 1.2000 0.055 Uiso 1 1 calc R . . H8B H 0.5945 0.1747 1.1804 0.055 Uiso 1 1 calc R . . C17 C 0.6560(5) 0.2580(2) 0.7243(3) 0.0530(8) Uani 1 1 d . . . H17 H 0.5837 0.2945 0.7469 0.064 Uiso 1 1 calc R . . C13 C 0.8728(5) 0.1542(2) 0.7628(3) 0.0536(8) Uani 1 1 d . . . H13 H 0.9468 0.1197 0.8114 0.064 Uiso 1 1 calc R . . C9 C 0.6568(4) 0.24409(17) 0.9640(2) 0.0385(6) Uani 1 1 d . . . C1 C 0.3510(4) 0.28976(19) 1.1790(2) 0.0445(6) Uani 1 1 d . . . C10 C 0.5222(4) 0.31000(19) 0.9391(2) 0.0470(7) Uani 1 1 d . . . H10A H 0.5677 0.3562 0.9085 0.056 Uiso 1 1 calc R . . H10B H 0.4185 0.2904 0.8867 0.056 Uiso 1 1 calc R . . C16 C 0.6568(5) 0.2566(2) 0.6181(3) 0.0561(8) Uani 1 1 d . . . H16 H 0.5835 0.2913 0.5694 0.067 Uiso 1 1 calc R . . C6 C 0.3979(5) 0.3576(2) 1.2424(3) 0.0576(8) Uani 1 1 d . . . H6 H 0.4830 0.3925 1.2304 0.069 Uiso 1 1 calc R . . C4 C 0.1950(6) 0.3233(3) 1.3423(3) 0.0701(11) Uani 1 1 d . . . H4 H 0.1455 0.3338 1.3982 0.084 Uiso 1 1 calc R . . C14 C 0.8754(5) 0.1532(2) 0.6564(3) 0.0585(8) Uani 1 1 d . . . H14 H 0.9511 0.1184 0.6342 0.070 Uiso 1 1 calc R . . C2 C 0.2212(5) 0.2404(2) 1.1981(3) 0.0611(9) Uani 1 1 d . . . H2 H 0.1854 0.1948 1.1554 0.073 Uiso 1 1 calc R . . C3 C 0.1432(6) 0.2572(3) 1.2794(4) 0.0719(11) Uani 1 1 d . . . H3 H 0.0560 0.2233 1.2907 0.086 Uiso 1 1 calc R . . C18 C 0.7657(6) 0.2042(3) 0.4692(3) 0.0680(10) Uani 1 1 d . . . C5 C 0.3206(6) 0.3748(3) 1.3237(3) 0.0688(11) Uani 1 1 d . . . H5 H 0.3535 0.4211 1.3656 0.083 Uiso 1 1 calc R . . C30 C 0.2641(4) 1.01854(19) 0.8144(2) 0.0437(6) Uani 1 1 d . . . C29 C 0.2608(4) 1.01863(18) 0.9270(2) 0.0410(6) Uani 1 1 d . . . C26 C 0.1242(4) 0.9900(2) 1.1653(2) 0.0471(7) Uani 1 1 d . . . H26A H 0.0740 1.0396 1.1848 0.057 Uiso 1 1 calc R . . H26B H 0.2116 0.9702 1.2277 0.057 Uiso 1 1 calc R . . C27 C 0.1398(4) 0.98743(17) 0.9754(2) 0.0399(6) Uani 1 1 d . . . C19 C -0.1212(4) 0.91716(19) 1.2097(2) 0.0430(6) Uani 1 1 d . . . C34 C 0.1627(5) 0.9698(2) 0.6335(3) 0.0542(8) Uani 1 1 d . . . H34 H 0.0904 0.9354 0.5840 0.065 Uiso 1 1 calc R . . C33 C 0.2727(5) 1.0219(2) 0.6017(3) 0.0544(8) Uani 1 1 d . . . C25 C -0.0189(4) 0.92617(17) 1.1278(2) 0.0431(6) Uani 1 1 d . . . H25 H 0.0388 0.8740 1.1235 0.052 Uiso 1 1 calc R . . C35 C 0.1579(5) 0.9678(2) 0.7398(3) 0.0500(7) Uani 1 1 d . . . H35 H 0.0825 0.9320 0.7607 0.060 Uiso 1 1 calc R . . C28 C -0.0310(4) 0.9439(2) 0.9405(2) 0.0483(7) Uani 1 1 d . . . H28A H -0.1013 0.9688 0.8754 0.058 Uiso 1 1 calc R . . H28B H -0.0096 0.8878 0.9244 0.058 Uiso 1 1 calc R . . C31 C 0.3759(6) 1.0713(3) 0.7811(3) 0.0681(11) Uani 1 1 d . . . H31 H 0.4498 1.1054 0.8303 0.082 Uiso 1 1 calc R . . C22 C -0.2985(5) 0.9014(3) 1.3650(3) 0.0620(9) Uani 1 1 d . . . H22 H -0.3557 0.8969 1.4186 0.074 Uiso 1 1 calc R . . C21 C -0.3254(5) 0.9693(2) 1.3000(3) 0.0607(9) Uani 1 1 d . . . H21 H -0.4026 1.0098 1.3083 0.073 Uiso 1 1 calc R . . C20 C -0.2367(5) 0.9765(2) 1.2227(3) 0.0555(8) Uani 1 1 d . . . H20 H -0.2551 1.0220 1.1785 0.067 Uiso 1 1 calc R . . C24 C -0.1008(5) 0.8495(2) 1.2734(3) 0.0570(8) Uani 1 1 d . . . H24 H -0.0260 0.8081 1.2643 0.068 Uiso 1 1 calc R . . C32 C 0.3772(6) 1.0730(3) 0.6754(3) 0.0718(11) Uani 1 1 d . . . H32 H 0.4503 1.1095 0.6536 0.086 Uiso 1 1 calc R . . C23 C -0.1899(6) 0.8415(3) 1.3514(3) 0.0684(11) Uani 1 1 d . . . H23 H -0.1749 0.7952 1.3941 0.082 Uiso 1 1 calc R . . C36 C 0.2789(6) 1.0243(3) 0.4891(3) 0.0672(10) Uani 1 1 d . . . N2 N 0.6968(3) 0.20917(15) 1.06110(18) 0.0402(5) Uani 1 1 d . . . N4 N 0.8535(4) 0.14572(17) 0.9771(2) 0.0486(6) Uani 1 1 d . . . N3 N 0.8162(3) 0.14980(17) 1.0694(2) 0.0486(6) Uani 1 1 d . . . N1 N 0.4753(4) 0.33557(15) 1.0344(2) 0.0468(6) Uani 1 1 d . . . H1 H 0.4694 0.3855 1.0529 0.056 Uiso 1 1 calc R . . N6 N 0.2061(3) 1.00674(16) 1.07902(19) 0.0427(5) Uani 1 1 d . . . N8 N 0.3901(4) 1.05561(18) 1.0030(2) 0.0533(7) Uani 1 1 d . . . N5 N -0.1297(3) 0.94503(16) 1.02083(19) 0.0434(5) Uani 1 1 d . . . H5A H -0.2399 0.9556 1.0069 0.052 Uiso 1 1 calc R . . N7 N 0.3568(4) 1.04787(19) 1.0964(2) 0.0560(7) Uani 1 1 d . . . F1 F 0.7959(9) 0.2730(3) 0.4338(3) 0.171(2) Uani 1 1 d . . . F3 F 0.6182(6) 0.1855(4) 0.4050(3) 0.157(2) Uani 1 1 d . . . F2 F 0.8792(9) 0.1575(5) 0.4489(3) 0.239(4) Uani 1 1 d . . . F6 F 0.4233(7) 1.0356(6) 0.4746(4) 0.231(4) Uani 1 1 d . . . F4 F 0.1843(12) 1.0671(6) 0.4330(4) 0.313(6) Uani 1 1 d . . . F5 F 0.2528(13) 0.9563(4) 0.4420(4) 0.244(4) 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 C12 0.0434(15) 0.0397(13) 0.0436(14) -0.0010(11) 0.0203(11) -0.0019(12) C7 0.0423(14) 0.0442(13) 0.0359(13) -0.0005(11) 0.0140(11) 0.0038(11) C15 0.0554(17) 0.0525(16) 0.0435(15) -0.0005(13) 0.0214(13) 0.0024(14) C11 0.0428(15) 0.0401(13) 0.0404(13) 0.0001(11) 0.0147(11) 0.0038(11) C8 0.0498(16) 0.0538(17) 0.0388(13) 0.0057(12) 0.0189(12) 0.0052(13) C17 0.060(2) 0.0565(18) 0.0484(17) 0.0049(14) 0.0252(15) 0.0160(15) C13 0.065(2) 0.0514(16) 0.0508(17) 0.0083(14) 0.0265(15) 0.0188(16) C9 0.0386(14) 0.0399(13) 0.0387(13) 0.0032(10) 0.0135(11) 0.0013(11) C1 0.0417(15) 0.0567(17) 0.0397(14) 0.0027(12) 0.0191(12) 0.0096(13) C10 0.0555(17) 0.0477(15) 0.0420(14) 0.0091(12) 0.0204(13) 0.0173(13) C16 0.061(2) 0.069(2) 0.0407(15) 0.0087(14) 0.0182(14) 0.0193(17) C6 0.0541(19) 0.070(2) 0.0532(18) -0.0089(16) 0.0224(15) -0.0068(16) C4 0.063(2) 0.103(3) 0.051(2) 0.012(2) 0.0253(17) 0.028(2) C14 0.077(2) 0.0561(18) 0.0542(18) 0.0015(15) 0.0376(17) 0.0147(18) C2 0.064(2) 0.0583(19) 0.070(2) -0.0001(17) 0.0338(18) -0.0055(17) C3 0.066(2) 0.086(3) 0.077(3) 0.011(2) 0.042(2) 0.000(2) C18 0.091(3) 0.075(2) 0.0450(18) -0.0043(17) 0.0298(19) 0.002(2) C5 0.067(2) 0.091(3) 0.0484(19) -0.0180(18) 0.0144(17) 0.010(2) C30 0.0470(15) 0.0465(15) 0.0434(14) -0.0037(12) 0.0219(12) -0.0055(12) C29 0.0409(14) 0.0441(14) 0.0409(13) -0.0070(11) 0.0159(11) -0.0041(11) C26 0.0479(16) 0.0623(18) 0.0330(13) -0.0006(12) 0.0139(11) -0.0055(14) C27 0.0442(14) 0.0422(14) 0.0353(12) -0.0033(10) 0.0141(11) -0.0029(11) C19 0.0455(15) 0.0488(15) 0.0359(13) 0.0001(11) 0.0133(11) -0.0019(12) C34 0.060(2) 0.062(2) 0.0450(16) -0.0109(14) 0.0214(14) -0.0118(16) C33 0.065(2) 0.0631(19) 0.0424(15) -0.0032(14) 0.0259(14) 0.0025(16) C25 0.0510(16) 0.0420(14) 0.0395(13) 0.0057(11) 0.0175(12) 0.0056(12) C35 0.0555(18) 0.0529(17) 0.0484(16) -0.0039(13) 0.0259(14) -0.0113(14) C28 0.0548(17) 0.0548(16) 0.0382(13) -0.0047(12) 0.0172(12) -0.0146(14) C31 0.073(2) 0.081(2) 0.057(2) -0.0143(18) 0.0307(18) -0.036(2) C22 0.060(2) 0.088(3) 0.0451(17) 0.0026(17) 0.0267(15) -0.0099(19) C21 0.063(2) 0.067(2) 0.060(2) -0.0013(16) 0.0306(17) 0.0081(17) C20 0.066(2) 0.0546(18) 0.0526(17) 0.0077(14) 0.0281(16) 0.0075(16) C24 0.062(2) 0.0589(19) 0.0561(19) 0.0151(15) 0.0259(16) 0.0091(16) C32 0.084(3) 0.082(3) 0.062(2) -0.0095(19) 0.041(2) -0.035(2) C23 0.075(3) 0.078(3) 0.055(2) 0.0235(19) 0.0222(19) 0.002(2) C36 0.076(2) 0.086(3) 0.0459(18) 0.0029(19) 0.0285(18) -0.003(2) N2 0.0417(12) 0.0436(12) 0.0369(11) 0.0066(9) 0.0135(9) 0.0053(10) N4 0.0498(14) 0.0497(13) 0.0488(14) 0.0072(11) 0.0176(11) 0.0111(12) N3 0.0457(13) 0.0565(14) 0.0455(13) 0.0097(12) 0.0158(11) 0.0176(12) N1 0.0588(16) 0.0435(13) 0.0456(13) 0.0035(10) 0.0272(12) 0.0104(11) N6 0.0409(13) 0.0532(14) 0.0355(11) -0.0019(10) 0.0128(9) -0.0027(10) N8 0.0481(14) 0.0708(18) 0.0435(13) -0.0083(12) 0.0163(11) -0.0150(13) N5 0.0454(13) 0.0498(13) 0.0385(12) -0.0025(10) 0.0174(10) -0.0046(11) N7 0.0479(14) 0.0753(19) 0.0462(14) -0.0105(13) 0.0149(11) -0.0146(14) F1 0.323(7) 0.142(3) 0.076(2) -0.010(2) 0.099(3) -0.102(4) F3 0.138(3) 0.280(6) 0.0535(16) -0.024(2) 0.0247(18) -0.074(4) F2 0.331(8) 0.340(8) 0.082(2) 0.060(4) 0.117(4) 0.241(7) F6 0.172(5) 0.462(13) 0.091(3) -0.011(5) 0.090(3) -0.071(6) F4 0.442(11) 0.446(12) 0.100(3) 0.140(5) 0.157(5) 0.355(11) F5 0.499(13) 0.187(5) 0.090(3) -0.052(3) 0.155(5) -0.124(7) _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 C12 C13 1.382(4) . ? C12 C17 1.383(5) . ? C12 C11 1.470(4) . ? C7 N1 1.461(4) . ? C7 C1 1.494(4) . ? C7 C8 1.515(4) . ? C7 H7 0.9800 . ? C15 C14 1.372(5) . ? C15 C16 1.382(5) . ? C15 C18 1.492(5) . ? C11 N4 1.370(4) . ? C11 C9 1.374(4) . ? C8 N2 1.461(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C17 C16 1.382(4) . ? C17 H17 0.9300 . ? C13 C14 1.388(5) . ? C13 H13 0.9300 . ? C9 N2 1.344(4) . ? C9 C10 1.493(4) . ? C1 C6 1.376(5) . ? C1 C2 1.384(5) . ? C10 N1 1.448(4) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C16 H16 0.9300 . ? C6 C5 1.385(5) . ? C6 H6 0.9300 . ? C4 C3 1.354(7) . ? C4 C5 1.378(7) . ? C4 H4 0.9300 . ? C14 H14 0.9300 . ? C2 C3 1.388(5) . ? C2 H2 0.9300 . ? C3 H3 0.9300 . ? C18 F2 1.263(6) . ? C18 F1 1.267(6) . ? C18 F3 1.278(6) . ? C5 H5 0.9300 . ? C30 C35 1.380(4) . ? C30 C31 1.388(5) . ? C30 C29 1.471(4) . ? C29 N8 1.360(4) . ? C29 C27 1.379(4) . ? C26 N6 1.464(4) . ? C26 C25 1.525(4) . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C27 N6 1.345(4) . ? C27 C28 1.490(4) . ? C19 C24 1.370(4) . ? C19 C20 1.378(5) . ? C19 C25 1.509(4) . ? C34 C33 1.363(5) . ? C34 C35 1.391(4) . ? C34 H34 0.9300 . ? C33 C32 1.371(6) . ? C33 C36 1.478(5) . ? C25 N5 1.464(4) . ? C25 H25 0.9800 . ? C35 H35 0.9300 . ? C28 N5 1.463(4) . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C31 C32 1.376(5) . ? C31 H31 0.9300 . ? C22 C23 1.349(6) . ? C22 C21 1.381(6) . ? C22 H22 0.9300 . ? C21 C20 1.377(5) . ? C21 H21 0.9300 . ? C20 H20 0.9300 . ? C24 C23 1.388(5) . ? C24 H24 0.9300 . ? C32 H32 0.9300 . ? C23 H23 0.9300 . ? C36 F4 1.138(6) . ? C36 F6 1.223(6) . ? C36 F5 1.264(7) . ? N2 N3 1.343(3) . ? N4 N3 1.311(4) . ? N1 H1 0.8600 . ? N6 N7 1.338(4) . ? N8 N7 1.315(4) . ? N5 H5A 0.8600 . ? 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 C13 C12 C17 118.6(3) . . ? C13 C12 C11 119.5(3) . . ? C17 C12 C11 121.9(3) . . ? N1 C7 C1 112.8(2) . . ? N1 C7 C8 107.2(2) . . ? C1 C7 C8 110.2(2) . . ? N1 C7 H7 108.9 . . ? C1 C7 H7 108.9 . . ? C8 C7 H7 108.9 . . ? C14 C15 C16 119.7(3) . . ? C14 C15 C18 121.4(3) . . ? C16 C15 C18 118.9(3) . . ? N4 C11 C9 108.1(3) . . ? N4 C11 C12 119.8(3) . . ? C9 C11 C12 131.8(3) . . ? N2 C8 C7 107.0(2) . . ? N2 C8 H8A 110.3 . . ? C7 C8 H8A 110.3 . . ? N2 C8 H8B 110.3 . . ? C7 C8 H8B 110.3 . . ? H8A C8 H8B 108.6 . . ? C16 C17 C12 120.7(3) . . ? C16 C17 H17 119.6 . . ? C12 C17 H17 119.6 . . ? C12 C13 C14 120.8(3) . . ? C12 C13 H13 119.6 . . ? C14 C13 H13 119.6 . . ? N2 C9 C11 104.4(2) . . ? N2 C9 C10 119.2(2) . . ? C11 C9 C10 136.3(3) . . ? C6 C1 C2 117.5(3) . . ? C6 C1 C7 122.9(3) . . ? C2 C1 C7 119.6(3) . . ? N1 C10 C9 110.9(2) . . ? N1 C10 H10A 109.4 . . ? C9 C10 H10A 109.4 . . ? N1 C10 H10B 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 108.0 . . ? C15 C16 C17 120.1(3) . . ? C15 C16 H16 119.9 . . ? C17 C16 H16 119.9 . . ? C1 C6 C5 121.3(4) . . ? C1 C6 H6 119.4 . . ? C5 C6 H6 119.4 . . ? C3 C4 C5 120.2(4) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C15 C14 C13 120.0(3) . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C1 C2 C3 121.6(4) . . ? C1 C2 H2 119.2 . . ? C3 C2 H2 119.2 . . ? C4 C3 C2 119.6(4) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? F2 C18 F1 104.6(5) . . ? F2 C18 F3 107.2(5) . . ? F1 C18 F3 102.0(5) . . ? F2 C18 C15 113.3(4) . . ? F1 C18 C15 114.7(4) . . ? F3 C18 C15 114.0(4) . . ? C4 C5 C6 119.8(4) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C35 C30 C31 118.6(3) . . ? C35 C30 C29 121.9(3) . . ? C31 C30 C29 119.5(3) . . ? N8 C29 C27 108.4(3) . . ? N8 C29 C30 120.8(3) . . ? C27 C29 C30 130.8(3) . . ? N6 C26 C25 109.2(2) . . ? N6 C26 H26A 109.8 . . ? C25 C26 H26A 109.8 . . ? N6 C26 H26B 109.8 . . ? C25 C26 H26B 109.8 . . ? H26A C26 H26B 108.3 . . ? N6 C27 C29 103.7(3) . . ? N6 C27 C28 119.7(3) . . ? C29 C27 C28 136.6(3) . . ? C24 C19 C20 118.3(3) . . ? C24 C19 C25 120.5(3) . . ? C20 C19 C25 121.2(3) . . ? C33 C34 C35 120.4(3) . . ? C33 C34 H34 119.8 . . ? C35 C34 H34 119.8 . . ? C34 C33 C32 119.2(3) . . ? C34 C33 C36 120.7(4) . . ? C32 C33 C36 120.0(4) . . ? N5 C25 C19 113.0(3) . . ? N5 C25 C26 111.3(2) . . ? C19 C25 C26 109.7(2) . . ? N5 C25 H25 107.6 . . ? C19 C25 H25 107.6 . . ? C26 C25 H25 107.6 . . ? C30 C35 C34 120.6(3) . . ? C30 C35 H35 119.7 . . ? C34 C35 H35 119.7 . . ? N5 C28 C27 113.2(2) . . ? N5 C28 H28A 108.9 . . ? C27 C28 H28A 108.9 . . ? N5 C28 H28B 108.9 . . ? C27 C28 H28B 108.9 . . ? H28A C28 H28B 107.8 . . ? C32 C31 C30 120.0(4) . . ? C32 C31 H31 120.0 . . ? C30 C31 H31 120.0 . . ? C23 C22 C21 120.5(3) . . ? C23 C22 H22 119.8 . . ? C21 C22 H22 119.8 . . ? C20 C21 C22 119.4(4) . . ? C20 C21 H21 120.3 . . ? C22 C21 H21 120.3 . . ? C21 C20 C19 121.0(3) . . ? C21 C20 H20 119.5 . . ? C19 C20 H20 119.5 . . ? C19 C24 C23 121.1(3) . . ? C19 C24 H24 119.4 . . ? C23 C24 H24 119.4 . . ? C33 C32 C31 121.3(3) . . ? C33 C32 H32 119.4 . . ? C31 C32 H32 119.4 . . ? C22 C23 C24 119.6(3) . . ? C22 C23 H23 120.2 . . ? C24 C23 H23 120.2 . . ? F4 C36 F6 106.9(7) . . ? F4 C36 F5 104.1(7) . . ? F6 C36 F5 95.6(6) . . ? F4 C36 C33 117.3(4) . . ? F6 C36 C33 116.0(4) . . ? F5 C36 C33 114.2(4) . . ? N3 N2 C9 111.7(2) . . ? N3 N2 C8 121.6(2) . . ? C9 N2 C8 126.4(2) . . ? N3 N4 C11 109.0(2) . . ? N4 N3 N2 106.9(2) . . ? C10 N1 C7 111.6(2) . . ? C10 N1 H1 124.2 . . ? C7 N1 H1 124.2 . . ? N7 N6 C27 112.3(2) . . ? N7 N6 C26 121.7(2) . . ? C27 N6 C26 126.0(3) . . ? N7 N8 C29 109.2(2) . . ? C28 N5 C25 112.0(3) . . ? C28 N5 H5A 124.0 . . ? C25 N5 H5A 124.0 . . ? N8 N7 N6 106.5(2) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 31.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.804 _refine_diff_density_min -0.499 _refine_diff_density_rms 0.061