Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name _publ_author_address _publ_author_footnote 'Catherine E Housecroft' ; ? # Address for author 1 ; ; ? # Footnote for author 1 ; 'Edwin C. Constable' ; ? # Address 2 ; ; ? # Footnote 2 ; 'Markus Neuburger' '' '' 'Sebastien Reymann' '' '' 'Silvia Schaffner' '' '' _publ_contact_author_name 'Catherine E Housecroft' _publ_contact_author_email CATHERINE.HOUSECROFT@UNIBAS.CH _publ_section_title ; A new twist to 3,6-bis(2-pyridyl)-1,2,4,5-tetrazine complexes of silver(I) ; _journal_coden_ASTM ? _journal_coeditor_code ? _journal_coeditor_name ? _journal_coeditor_notes ? _journal_date_accepted ? _journal_date_from_coeditor ? _journal_date_printers_final ? _journal_date_printers_first ? _journal_date_proofs_in ? _journal_date_proofs_out ? # PROCESSING SUMMARY (IUCr Office Use Only): _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_issue ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? _journal_techeditor_code ? _journal_techeditor_notes ? _publ_contact_author_address ; Chemical Crystallography Laboratory, Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK. ; _publ_contact_author_fax '+44 1865 285018' _publ_contact_author_phone '+44 1865 285024' # Check this file using the IUCr facility at: # http://journals.iucr.org/services/cif/checking/checkfull.html # The content below is held in the file 'script/refcif.dat'. This is a text # file which you may edit to reflect local conditions. # Items which need looking at are represented by a '?'. # Items for which there are choices are prefixed with 'choose from'. _publ_contact_letter ; Please consider this CIF submission for publication as a Short Format Paper in Acta Crystallographica C. The figures have been sent by mail. ; _publ_requested_category CO # choose from: FI FM FO CI CM CO AD _publ_requested_coeditor_name 'Prof William Clegg' # Attachment 'Tetrazine_silver.cif' data_CRYSTALS_cif _database_code_depnum_ccdc_archive 'CCDC 679521' _audit_creation_date 05-10-12 _audit_creation_method CRYSTALS_ver_12.24 _oxford_structure_analysis_title '11111155 sr225e_2_173k' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 18.2439(2) _cell_length_b 14.5934(2) _cell_length_c 8.42800(10) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2243.88(5) _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P m m n ' _symmetry_space_group_name_Hall '-P 2ab 2a' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y,z x+1/2,-y,-z x,-y+1/2,z -x,y+1/2,-z -x+1/2,-y+1/2,z x+1/2,y+1/2,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7997 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Ag -1.0850 1.1010 19.2808 0.6446 16.6885 7.4726 4.8045 24.6605 1.0463 99.8156 5.1790 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4' F 0.0140 0.0100 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 _chemical_formula_sum 'C40 H27 Ag2 F6 N19 O6 S2' _chemical_formula_moiety 'C36 H24 Ag2 N18, 2(C F3 O3 S), C2 H3 N' _chemical_compound_source ? _chemical_formula_weight 1263.63 _cell_measurement_reflns_used 3051 _cell_measurement_theta_min 3 _cell_measurement_theta_max 28 _cell_measurement_temperature 173 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_min 0.08 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_max 0.16 _exptl_crystal_density_diffrn 1.870 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 1256 _exptl_absorpt_coefficient_mu 1.064 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Denzo/Scalepack (Otwinowski & Minor, 1996)' _exptl_absorpt_correction_T_min 0.88 _exptl_absorpt_correction_T_max 0.92 # Sheldrick geometric definitions 0.88 0.92 _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' _computing_data_collection 'COLLECT (Nonius BV, 1997)' _computing_data_reduction 'Denzo/Scalepack (Otwinowski & Minor, 1996)' _computing_cell_refinement 'Denzo/Scalepack (Otwinowski & Minor, 1996)' _computing_structure_solution 'SIR92 (Altomare et al, 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 173 _diffrn_reflns_number 5349 _reflns_number_total 2860 _diffrn_reflns_av_R_equivalents 0.006 # Number of reflections with Friedels Law is 2860 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 2675 _diffrn_reflns_theta_min 3.006 _diffrn_reflns_theta_max 27.871 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.871 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _reflns_limit_h_min 0 _reflns_limit_h_max 23 _reflns_limit_k_min 0 _reflns_limit_k_max 19 _reflns_limit_l_min 0 _reflns_limit_l_max 11 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -1.03 _refine_diff_density_max 1.47 _refine_ls_number_reflns 2081 _refine_ls_number_restraints 6 _refine_ls_number_parameters 200 #_refine_ls_R_factor_ref 0.0632 _refine_ls_wR_factor_ref 0.0719 _refine_ls_goodness_of_fit_ref 1.0738 #_reflns_number_all 2853 _refine_ls_R_factor_all 0.0996 _refine_ls_wR_factor_all 0.1010 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>1.20u(I) _reflns_number_gt 2081 _refine_ls_R_factor_gt 0.0632 _refine_ls_wR_factor_gt 0.0719 _refine_ls_shift/su_max 0.000131 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.576 0.606 0.210 ; _publ_section_abstract # Text of the abstract ; ? ; _publ_section_comment # Text of the paper ; ? ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions # Captions to figures ; ? ; _publ_section_exptl_refinement # see also _refine_ls_hydrogen ; H atoms placed geometrically after each cycle ; _publ_section_exptl_prep ; ? ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo G., Guagliardi A., Burla M.C., Polidori, G. & Camalli, M. (1994) SIR92 - a program for automatic solution of crystal structures by direct methods. J. Appl. Cryst. (27), 435-435 Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius BV, COLLECT Software, (1997-2001) Otwinowski, Z. & Minor, W. (1996), Processing of X-ray Diffraction Data Collected in Oscillation Mode. Methods Enzymol. 276, 1997, 307-326. Ed Carter, C.W. & Sweet, R.M., Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994), Acta Cryst, A50, 411-437 Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atoms attached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens Ag1 Ag 0.13240(3) 0.2500 0.46562(5) 0.0680 1.0000 Uani S T . . . . S1 S 0.2500 0.49133(16) 0.1476(2) 0.0768 1.0000 Uani S T . . . . N1 N 0.0625(2) 0.3782(3) 0.5855(4) 0.0710 1.0000 Uani . . . . . . N2 N 0.21373(19) 0.3653(3) 0.6040(4) 0.0623 1.0000 Uani . . . . . . N3 N 0.2133(2) 0.5190(4) 0.6922(5) 0.0746 1.0000 Uani . . . . . . N4 N 0.0637(5) 0.2500 0.2177(6) 0.0973 1.0000 Uani S T . . . . N5 N 0.2132(4) 0.2500 0.2250(5) 0.0750 1.0000 Uani S T . . . . N6 N 0.2139(5) 0.2500 -0.0565(7) 0.1003 1.0000 Uani S T . . . . N7 N 0.1438(9) 0.7500 0.543(2) 0.1119 0.5000 Uani S T . . . . C1 C -0.0110(3) 0.3828(5) 0.5935(6) 0.0822 1.0000 Uani . . . . . . C2 C -0.0493(3) 0.4463(5) 0.6853(7) 0.0840 1.0000 Uani . . . . . . C3 C -0.0104(3) 0.5041(5) 0.7786(7) 0.0824 1.0000 Uani . . . . . . C4 C 0.0653(3) 0.5029(4) 0.7715(6) 0.0756 1.0000 Uani . . . . . . C5 C 0.0990(2) 0.4407(4) 0.6726(5) 0.0660 1.0000 Uani . . . . . . C6 C 0.1796(2) 0.4401(4) 0.6574(5) 0.0603 1.0000 Uani . . . . . . C7 C -0.0098(6) 0.2500 0.2135(8) 0.0992 1.0000 Uani S T . . . . C8 C -0.0515(6) 0.2500 0.0759(9) 0.0831 1.0000 Uani S T . . . . C9 C -0.0139(6) 0.2500 -0.0646(8) 0.0784 1.0000 Uani S T . . . . C10 C 0.0614(5) 0.2500 -0.0643(7) 0.0725 1.0000 Uani S T . . . . C11 C 0.0984(5) 0.2500 0.0785(7) 0.0666 1.0000 Uani S T . . . . C12 C 0.1796(5) 0.2500 0.0827(7) 0.0742 1.0000 Uani S T . . . . C13 C 0.2500 0.6149(6) 0.1136(8) 0.0726 1.0000 Uani S T . . . . C14 C 0.2103(4) 0.750000(7) 0.5700 0.0779 0.5000 Uani S T . . . . C15 C 0.2897(4) 0.750000(7) 0.5700 0.0779 0.5000 Uani S T . . . . F1 F 0.2500 0.6402(4) -0.0380(7) 0.1326 1.0000 Uani S T . . . . F2 F 0.1920(2) 0.6571(4) 0.1678(9) 0.1548 1.0000 Uani . . . . . . O1 O 0.2500 0.4905(8) 0.3149(10) 0.1529 1.0000 Uani S T . . . . O2 O 0.1850(2) 0.4635(4) 0.0725(8) 0.1172 1.0000 Uani . . . . . . H11 H -0.0388 0.3396 0.5318 0.0969 1.0000 Uiso . . . . . . H21 H -0.1020 0.4490 0.6825 0.1002 1.0000 Uiso . . . . . . H31 H -0.0352 0.5463 0.8487 0.0984 1.0000 Uiso . . . . . . H41 H 0.0941 0.5448 0.8342 0.0903 1.0000 Uiso . . . . . . H71 H -0.0354 0.2500 0.3125 0.1189 1.0000 Uiso . . . . . . H81 H -0.1043 0.2500 0.0799 0.0996 1.0000 Uiso . . . . . . H91 H -0.0402 0.2500 -0.1636 0.0939 1.0000 Uiso . . . . . . H101 H 0.0881 0.2500 -0.1627 0.0869 1.0000 Uiso . . . . . . H151 H 0.3068 0.7500 0.6774 0.0929 0.5000 Uiso . . . . . . H152 H 0.3068 0.8037 0.5163 0.0929 0.5000 Uiso . . . . . . 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 Ag1 0.0539(3) 0.1234(5) 0.0269(3) 0.0000 -0.00057(16) 0.0000 S1 0.0436(7) 0.1326(16) 0.0542(9) 0.0268(10) 0.0000 0.0000 N1 0.063(2) 0.109(3) 0.0401(16) 0.0153(19) 0.0018(16) -0.007(2) N2 0.0581(18) 0.095(3) 0.0335(14) 0.0147(17) -0.0016(13) 0.0017(19) N3 0.064(2) 0.105(3) 0.055(2) 0.011(2) -0.0001(18) 0.006(2) N4 0.102(5) 0.161(7) 0.028(2) 0.0000 -0.005(3) 0.0000 N5 0.104(4) 0.097(4) 0.024(2) 0.0000 -0.004(2) 0.0000 N6 0.113(5) 0.160(7) 0.028(2) 0.0000 -0.002(3) 0.0000 N7 0.060(8) 0.166(17) 0.110(15) 0.0000 -0.010(7) 0.0000 C1 0.061(3) 0.129(5) 0.056(3) 0.026(3) 0.001(2) -0.009(3) C2 0.061(3) 0.127(5) 0.064(3) 0.034(3) 0.008(2) 0.008(3) C3 0.065(3) 0.116(4) 0.066(3) 0.016(3) 0.001(3) 0.019(3) C4 0.064(3) 0.104(4) 0.058(3) 0.012(3) -0.005(2) 0.018(3) C5 0.057(2) 0.102(3) 0.0390(18) 0.019(2) -0.0055(17) 0.002(2) C6 0.058(2) 0.087(3) 0.0357(17) 0.0154(19) -0.0031(16) -0.001(2) C7 0.104(6) 0.159(8) 0.034(3) 0.0000 -0.001(4) 0.0000 C8 0.112(6) 0.094(5) 0.044(3) 0.0000 -0.014(4) 0.0000 C9 0.109(6) 0.090(5) 0.037(3) 0.0000 -0.016(3) 0.0000 C10 0.113(6) 0.076(4) 0.029(2) 0.0000 -0.004(3) 0.0000 C11 0.096(5) 0.072(4) 0.032(2) 0.0000 -0.003(3) 0.0000 C12 0.101(5) 0.099(5) 0.023(2) 0.0000 -0.002(3) 0.0000 C13 0.046(3) 0.116(6) 0.055(3) -0.003(4) 0.0000 0.0000 C14 0.048(3) 0.111(6) 0.075(4) 0.000000(7) 0.0121 0.000000(7) C15 0.048(3) 0.111(6) 0.075(4) 0.000000(7) -0.0121 0.000000(7) F1 0.220(8) 0.103(4) 0.075(4) 0.012(3) 0.0000 0.0000 F2 0.095(3) 0.147(4) 0.222(6) 0.029(4) 0.065(4) 0.011(3) O1 0.156(7) 0.230(10) 0.072(4) 0.072(6) 0.0000 0.0000 O2 0.077(3) 0.123(3) 0.151(5) 0.037(3) -0.042(3) -0.019(3) _refine_ls_extinction_coef 130(20) _refine_ls_extinction_method 'Larson 1970 Crystallographic Computing eq 22' _oxford_refine_ls_scale 0.1696(7) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Ag1 . N1 5_555 2.480(5) yes Ag1 . N2 5_555 2.528(4) yes Ag1 . N1 . 2.480(5) yes Ag1 . N2 . 2.528(4) yes Ag1 . N4 . 2.437(6) yes Ag1 . N5 . 2.507(6) yes S1 . O2 3_555 1.405(5) yes S1 . C13 . 1.826(9) yes S1 . O1 . 1.410(8) yes S1 . O2 . 1.405(5) yes N1 . C1 . 1.345(6) yes N1 . C5 . 1.348(7) yes N2 . N2 3_555 1.323(7) yes N2 . C6 . 1.335(6) yes N3 . N3 3_555 1.340(8) yes N3 . C6 . 1.338(7) yes N4 . C7 . 1.341(13) yes N4 . C11 . 1.333(9) yes N5 . N5 3_555 1.344(14) yes N5 . C12 . 1.347(8) yes N6 . N6 3_555 1.317(18) yes N6 . C12 . 1.330(9) yes N7 . H152 3_555 1.216 no N7 . H152 7_565 1.216 no N7 . C15 7_565 1.235(17) yes N7 . C14 . 1.235(17) yes C1 . C2 . 1.395(9) yes C1 . H11 . 0.961 no C2 . C3 . 1.354(9) yes C2 . H21 . 0.961 no C3 . C4 . 1.383(7) yes C3 . H31 . 0.966 no C4 . C5 . 1.377(8) yes C4 . H41 . 0.965 no C5 . C6 . 1.475(6) yes C7 . C8 . 1.386(11) yes C7 . H71 . 0.956 no C8 . C9 . 1.368(12) yes C8 . H81 . 0.963 no C9 . C10 . 1.375(13) yes C9 . H91 . 0.962 no C10 . C11 . 1.379(9) yes C10 . H101 . 0.961 no C11 . C12 . 1.482(12) yes C13 . F2 3_555 1.307(6) yes C13 . F1 . 1.330(9) yes C13 . F2 . 1.307(6) yes C14 . C15 . 1.448(13) yes C15 . H152 5_565 0.958 no C15 . H151 . 0.958 no C15 . H152 . 0.958 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag N1 5_555 Ag1 . N2 5_555 67.18(14) yes N1 5_555 Ag1 . N1 . 97.97(18) yes N2 5_555 Ag1 . N1 . 128.04(12) yes N1 5_555 Ag1 . N2 . 128.04(12) yes N2 5_555 Ag1 . N2 . 83.42(17) yes N1 . Ag1 . N2 . 67.18(14) yes N1 5_555 Ag1 . N4 . 94.85(15) yes N2 5_555 Ag1 . N4 . 134.23(10) yes N1 . Ag1 . N4 . 94.85(15) yes N2 . Ag1 . N4 . 134.23(10) yes N1 5_555 Ag1 . N5 . 129.20(9) yes N2 5_555 Ag1 . N5 . 91.61(13) yes N1 . Ag1 . N5 . 129.20(9) yes N2 . Ag1 . N5 . 91.61(13) yes N4 . Ag1 . N5 . 67.0(2) yes O2 3_555 S1 . C13 . 102.4(2) yes O2 3_555 S1 . O1 . 116.6(3) yes C13 . S1 . O1 . 99.5(5) yes O2 3_555 S1 . O2 . 115.3(6) yes C13 . S1 . O2 . 102.4(2) yes O1 . S1 . O2 . 116.6(3) yes Ag1 . N1 . C1 . 124.9(4) yes Ag1 . N1 . C5 . 118.5(3) yes C1 . N1 . C5 . 115.6(5) yes Ag1 . N2 . N2 3_555 125.94(9) yes Ag1 . N2 . C6 . 115.2(3) yes N2 3_555 N2 . C6 . 117.8(3) yes N3 3_555 N3 . C6 . 117.3(3) yes Ag1 . N4 . C7 . 122.5(5) yes Ag1 . N4 . C11 . 120.7(6) yes C7 . N4 . C11 . 116.8(7) yes Ag1 . N5 . N5 3_555 126.01(14) yes Ag1 . N5 . C12 . 116.9(5) yes N5 3_555 N5 . C12 . 117.1(5) yes N6 3_555 N6 . C12 . 118.1(5) yes H152 3_555 N7 . H152 7_565 80.244 no H152 3_555 N7 . C15 7_565 45.985 no H152 7_565 N7 . C15 7_565 45.985 no H152 3_555 N7 . C14 . 45.984 no H152 7_565 N7 . C14 . 45.984 no N1 . C1 . C2 . 124.1(6) yes N1 . C1 . H11 . 117.758 no C2 . C1 . H11 . 118.136 no C1 . C2 . C3 . 118.2(5) yes C1 . C2 . H21 . 120.919 no C3 . C2 . H21 . 120.831 no C2 . C3 . C4 . 119.4(6) yes C2 . C3 . H31 . 120.428 no C4 . C3 . H31 . 120.195 no C3 . C4 . C5 . 118.8(6) yes C3 . C4 . H41 . 120.834 no C5 . C4 . H41 . 120.399 no C4 . C5 . N1 . 123.7(4) yes C4 . C5 . C6 . 120.1(5) yes N1 . C5 . C6 . 116.2(4) yes C5 . C6 . N3 . 115.7(4) yes C5 . C6 . N2 . 119.9(4) yes N3 . C6 . N2 . 124.3(4) yes N4 . C7 . C8 . 124.7(8) yes N4 . C7 . H71 . 117.720 no C8 . C7 . H71 . 117.531 no C7 . C8 . C9 . 116.7(9) yes C7 . C8 . H81 . 121.256 no C9 . C8 . H81 . 122.052 no C8 . C9 . C10 . 120.0(7) yes C8 . C9 . H91 . 120.096 no C10 . C9 . H91 . 119.949 no C9 . C10 . C11 . 119.4(7) yes C9 . C10 . H101 . 120.313 no C11 . C10 . H101 . 120.336 no C10 . C11 . N4 . 122.4(8) yes C10 . C11 . C12 . 120.6(6) yes N4 . C11 . C12 . 117.0(6) yes C11 . C12 . N5 . 118.4(6) yes C11 . C12 . N6 . 116.7(6) yes N5 . C12 . N6 . 124.8(8) yes S1 . C13 . F2 3_555 114.2(4) yes S1 . C13 . F1 . 115.1(6) yes F2 3_555 C13 . F1 . 101.8(5) yes S1 . C13 . F2 . 114.2(4) yes F2 3_555 C13 . F2 . 108.2(8) yes F1 . C13 . F2 . 101.8(5) yes N7 . C14 . C15 . 169.5(9) yes C14 . C15 . H151 . 109.047 no H152 5_565 C15 . H151 . 109.891 no C14 . C15 . H152 . 109.047 no H151 . C15 . H152 . 109.892 no _refine_special_details ; The restraints have been used to control the refinement of positions and U-values of the disordered CH3CN situated on a mirror plane. ;