# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_coden_Cambridge 222 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Louis Rendina' 'Jack K. Clegg' 'Margaret M. Harding' 'David Schilter ' _publ_contact_author_name 'Louis Rendina' _publ_contact_author_email RENDINA@CHEM.USYD.EDU.AU _publ_section_title ; Platinum(II) and Palladium(II) Metallacycles Derived from Cationic 4,4?-Bipyridinium, 3-Aminopyrazinium and 2-Aminopyrimidinium Ligands ; # Attachment '16.CIF' data_lj215sad _database_code_depnum_ccdc_archive 'CCDC 743958' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H18 N6, C0.95 F3.15 O2.85 P0.05 S0.95, C F3 O3 S' _chemical_formula_sum ' C17.95 H18 F6.15 N6 O5.85 P0.05 S1.95 ' _chemical_formula_weight 592.32 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' S S 0.1246 0.1234 '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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M p-1 _symmetry_space_group_name_Hall '-p 1' _symmetry_intl_tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.6224(4) _cell_length_b 11.2521(5) _cell_length_c 12.3853(5) _cell_angle_alpha 98.435(2) _cell_angle_beta 112.739(2) _cell_angle_gamma 100.330(2) _cell_volume 1181.73(9) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 7706 _cell_measurement_theta_min 2.303 _cell_measurement_theta_max 39.471 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.250 _exptl_crystal_size_min 0.200 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.665 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 604 _exptl_absorpt_coefficient_mu 0.322 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.859 _exptl_absorpt_correction_T_max 0.937 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1999)' _exptl_special_details ; The crystal was coated in Exxon Paratone N hydrocarbon oil and mounted on a thin mohair fibre attached to a copper pin. Upon mounting on the diffractometer, the crystal was quenched to 150(K) under a cold nitrogen gas stream supplied by an Oxford Cryosystems Cryostream and data were collected at this temperature. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type APEXII-FR591 _diffrn_measurement_method \w+\f _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 79449 _diffrn_reflns_av_R_equivalents 0.0305 _diffrn_reflns_av_sigmaI/netI 0.0238 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 40.05 _reflns_number_total 14574 _reflns_number_gt 12323 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX (Bruker-Nonius, 2003)' _computing_cell_refinement 'SAINT (Bruker-Nonius, 2003)' _computing_data_reduction 'SAINT (Bruker-Nonius, 2003), XPREP (Bruker-Nonius, 2003)' _computing_structure_solution 'SIR97 (Altomare, et. al. 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ;ORTEP-3 (Farrugia, 1997) WINGX-32 (Farrugia, 1999) POV-Ray 3.5 (Cason, 2002) WebLab ViewerPro 3.7 (Molecular Simulations, 2000) ; _computing_publication_material 'enCIFer 1.1 (CCDC, 2005)' _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^)+(0.0496P)^2^+0.2401P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 14574 _refine_ls_number_parameters 365 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0451 _refine_ls_R_factor_gt 0.0357 _refine_ls_wR_factor_ref 0.0982 _refine_ls_wR_factor_gt 0.0931 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.46091(7) 0.39260(6) 0.58830(6) 0.01469(9) Uani 1 1 d . . . C2 C 0.41268(8) 0.22881(6) 0.42525(6) 0.01662(10) Uani 1 1 d . . . H2 H 0.3438 0.1579 0.3633 0.020 Uiso 1 1 calc R . . C3 C 0.56046(8) 0.27172(7) 0.43584(7) 0.01883(11) Uani 1 1 d . . . H3 H 0.5961 0.2330 0.3817 0.023 Uiso 1 1 calc R . . C4 C 0.65735(8) 0.37552(7) 0.53034(7) 0.01950(11) Uani 1 1 d . . . H4 H 0.7623 0.4044 0.5419 0.023 Uiso 1 1 calc R . . C5 C 0.20431(8) 0.23986(6) 0.49649(7) 0.01862(11) Uani 1 1 d . . . H5A H 0.1374 0.2928 0.4581 0.022 Uiso 1 1 calc R . . H5B H 0.2123 0.2477 0.5795 0.022 Uiso 1 1 calc R . . C6 C 0.12713(7) 0.10632(6) 0.42704(6) 0.01515(10) Uani 1 1 d . . . C7 C -0.00109(7) 0.07807(6) 0.31493(6) 0.01477(9) Uani 1 1 d . . . H7 H -0.0353 0.1432 0.2799 0.018 Uiso 1 1 calc R . . C8 C -0.07871(7) -0.04575(6) 0.25456(6) 0.01455(9) Uani 1 1 d . . . C9 C -0.02673(8) -0.14102(6) 0.30594(6) 0.01761(10) Uani 1 1 d . . . H9 H -0.0794 -0.2253 0.2649 0.021 Uiso 1 1 calc R . . C10 C 0.10160(9) -0.11324(7) 0.41684(7) 0.01930(11) Uani 1 1 d . . . H10 H 0.1371 -0.1784 0.4510 0.023 Uiso 1 1 calc R . . C11 C 0.17811(8) 0.01055(7) 0.47775(6) 0.01808(11) Uani 1 1 d . . . H11 H 0.2651 0.0297 0.5539 0.022 Uiso 1 1 calc R . . C12 C -0.22407(8) -0.07758(7) 0.13817(6) 0.01865(11) Uani 1 1 d . . . H12A H -0.3131 -0.1229 0.1502 0.022 Uiso 1 1 calc R . . H12B H -0.2467 0.0004 0.1168 0.022 Uiso 1 1 calc R . . C13 C -0.34255(7) -0.23129(6) -0.05811(6) 0.01438(9) Uani 1 1 d . . . C14 C -0.19644(9) -0.30803(7) -0.14676(7) 0.02086(12) Uani 1 1 d . . . H14 H -0.1901 -0.3653 -0.2081 0.025 Uiso 1 1 calc R . . C15 C -0.05856(8) -0.22181(8) -0.06075(7) 0.02111(12) Uani 1 1 d . . . H15 H 0.0379 -0.2153 -0.0667 0.025 Uiso 1 1 calc R . . C16 C -0.06982(8) -0.14783(7) 0.03172(6) 0.01778(11) Uani 1 1 d . . . H16 H 0.0212 -0.0906 0.0936 0.021 Uiso 1 1 calc R . . C17 C 0.84023(13) 0.48774(9) 0.13731(9) 0.03007(17) Uani 1 1 d . . . N1 N 0.60938(7) 0.43549(6) 0.60445(6) 0.01925(10) Uani 1 1 d . . . N2 N 0.41072(7) 0.45525(6) 0.65904(6) 0.01875(10) Uani 1 1 d . . . H2A H 0.4739 0.5226 0.7144 0.023 Uiso 1 1 calc R . . H2B H 0.3143 0.4294 0.6505 0.023 Uiso 1 1 calc R . . N3 N 0.36327(6) 0.28697(5) 0.50283(5) 0.01410(8) Uani 1 1 d . . . N4 N -0.21015(6) -0.15534(5) 0.03608(5) 0.01422(8) Uani 1 1 d . . . N5 N -0.48149(7) -0.22844(6) -0.06371(6) 0.01965(11) Uani 1 1 d . . . H5C H -0.5658 -0.2787 -0.1235 0.024 Uiso 1 1 calc R . . H5D H -0.4899 -0.1763 -0.0077 0.024 Uiso 1 1 calc R . . N6 N -0.33434(7) -0.31301(6) -0.14620(5) 0.01821(10) Uani 1 1 d . . . S1 S 0.891961(19) 0.452756(15) 0.285530(16) 0.01745(4) Uani 1 1 d . . . S2 S 0.40213(2) -0.036053(16) 0.174004(15) 0.01436(3) Uani 0.95 1 d P A 1 O4 O 0.28545(12) 0.02476(8) 0.18360(10) 0.02041(14) Uani 0.95 1 d P A 1 O5 O 0.37176(9) -0.09114(7) 0.05095(6) 0.02166(12) Uani 0.95 1 d P A 1 O6 O 0.56254(12) 0.03020(13) 0.25092(10) 0.02409(17) Uani 0.95 1 d P A 1 C18 C 0.37474(10) -0.17098(8) 0.23661(8) 0.02258(13) Uani 0.95 1 d P A 1 F4 F 0.23022(8) -0.24385(7) 0.17932(7) 0.03557(16) Uani 0.95 1 d P A 1 F5 F 0.47222(10) -0.24001(7) 0.22917(8) 0.03858(16) Uani 0.95 1 d P A 1 F6 F 0.40568(9) -0.13530(8) 0.35280(6) 0.03681(15) Uani 0.95 1 d P A 1 P1 P 0.3990(6) -0.0888(5) 0.2112(5) 0.0291(7) Uiso 0.05 1 d P B 2 F7 F 0.5111(15) -0.1839(13) 0.2365(11) 0.0291(7) Uiso 0.05 1 d P B 2 F8 F 0.4336(14) -0.0590(12) 0.3563(11) 0.0291(7) Uiso 0.05 1 d P B 2 F9 F 0.2510(17) -0.2012(13) 0.1815(13) 0.0291(7) Uiso 0.05 1 d P B 2 F10 F 0.291(3) 0.004(2) 0.190(2) 0.0291(7) Uiso 0.05 1 d P B 2 F11 F 0.372(2) -0.1107(16) 0.0727(15) 0.0291(7) Uiso 0.05 1 d P B 2 F12 F 0.543(3) 0.032(3) 0.233(2) 0.0291(7) Uiso 0.05 1 d P B 2 O1 O 0.75252(7) 0.36454(6) 0.27036(6) 0.02503(11) Uani 1 1 d . . . O2 O 1.02494(8) 0.40288(7) 0.30458(7) 0.02890(13) Uani 1 1 d . . . O3 O 0.92253(8) 0.57256(6) 0.36415(6) 0.02629(12) Uani 1 1 d . . . F1 F 0.72343(11) 0.54307(8) 0.11132(7) 0.0526(2) Uani 1 1 d . . . F2 F 0.79425(10) 0.38481(7) 0.05085(6) 0.04206(16) Uani 1 1 d . . . F3 F 0.95933(12) 0.56456(8) 0.13416(8) 0.0574(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0140(2) 0.0122(2) 0.0150(2) -0.00090(17) 0.00538(17) 0.00171(16) C2 0.0172(2) 0.0159(2) 0.0147(2) -0.00121(18) 0.00734(19) 0.00197(18) C3 0.0192(3) 0.0184(3) 0.0196(3) 0.0003(2) 0.0111(2) 0.0034(2) C4 0.0157(3) 0.0186(3) 0.0228(3) 0.0001(2) 0.0094(2) 0.00216(19) C5 0.0136(2) 0.0168(2) 0.0206(3) -0.0046(2) 0.0073(2) -0.00038(18) C6 0.0119(2) 0.0149(2) 0.0146(2) -0.00123(18) 0.00436(17) 0.00082(16) C7 0.0140(2) 0.0140(2) 0.0139(2) 0.00101(17) 0.00452(17) 0.00311(17) C8 0.0126(2) 0.0149(2) 0.0124(2) -0.00069(17) 0.00331(16) 0.00244(16) C9 0.0177(3) 0.0136(2) 0.0182(3) 0.00078(19) 0.0060(2) 0.00235(18) C10 0.0194(3) 0.0179(3) 0.0191(3) 0.0054(2) 0.0059(2) 0.0061(2) C11 0.0143(2) 0.0208(3) 0.0150(2) 0.0023(2) 0.00287(18) 0.00408(19) C12 0.0137(2) 0.0238(3) 0.0133(2) -0.0038(2) 0.00275(18) 0.0062(2) C13 0.0114(2) 0.0153(2) 0.0132(2) -0.00131(17) 0.00417(16) 0.00187(16) C14 0.0182(3) 0.0260(3) 0.0175(3) -0.0018(2) 0.0082(2) 0.0077(2) C15 0.0140(3) 0.0304(3) 0.0186(3) 0.0009(2) 0.0081(2) 0.0065(2) C16 0.0113(2) 0.0233(3) 0.0160(2) 0.0006(2) 0.00496(18) 0.00316(19) C17 0.0395(5) 0.0238(3) 0.0273(4) 0.0024(3) 0.0167(3) 0.0062(3) N1 0.0143(2) 0.0174(2) 0.0219(3) -0.00246(19) 0.00750(18) 0.00039(17) N2 0.0170(2) 0.0153(2) 0.0205(2) -0.00449(18) 0.00863(19) 0.00175(17) N3 0.01304(19) 0.01307(19) 0.01325(19) -0.00153(15) 0.00514(15) 0.00121(14) N4 0.01019(18) 0.0169(2) 0.01216(19) -0.00130(15) 0.00353(14) 0.00202(15) N5 0.0106(2) 0.0233(3) 0.0187(2) -0.00574(19) 0.00474(17) 0.00141(17) N6 0.0154(2) 0.0193(2) 0.0162(2) -0.00366(18) 0.00609(17) 0.00371(17) S1 0.01220(6) 0.01531(6) 0.02144(7) -0.00285(5) 0.00724(5) 0.00110(4) S2 0.01435(7) 0.01543(7) 0.01350(6) 0.00172(5) 0.00604(5) 0.00539(5) O4 0.0190(2) 0.0213(4) 0.0213(3) 0.0011(3) 0.0082(2) 0.0102(2) O5 0.0286(3) 0.0245(3) 0.0149(3) 0.00305(19) 0.0110(2) 0.0114(2) O6 0.0148(3) 0.0258(3) 0.0251(5) 0.0005(3) 0.0050(3) 0.0023(3) C18 0.0212(3) 0.0268(3) 0.0232(3) 0.0117(3) 0.0097(2) 0.0092(3) F4 0.0282(3) 0.0290(3) 0.0435(4) 0.0142(3) 0.0110(3) -0.0018(2) F5 0.0431(4) 0.0355(3) 0.0554(4) 0.0272(3) 0.0266(3) 0.0272(3) F6 0.0390(3) 0.0552(4) 0.0219(3) 0.0190(3) 0.0144(2) 0.0142(3) O1 0.0154(2) 0.0268(3) 0.0252(3) -0.0015(2) 0.00769(18) -0.00460(18) O2 0.0186(2) 0.0305(3) 0.0380(3) 0.0016(2) 0.0130(2) 0.0102(2) O3 0.0264(3) 0.0186(2) 0.0272(3) -0.00697(19) 0.0104(2) 0.00235(19) F1 0.0687(6) 0.0549(5) 0.0371(4) 0.0156(3) 0.0141(4) 0.0384(4) F2 0.0617(5) 0.0341(3) 0.0256(3) -0.0043(2) 0.0190(3) 0.0092(3) F3 0.0723(6) 0.0473(4) 0.0545(5) 0.0135(4) 0.0392(4) -0.0094(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N2 1.3288(9) . ? C1 N1 1.3481(9) . ? C1 N3 1.3702(8) . ? C2 N3 1.3630(9) . ? C2 C3 1.3650(10) . ? C2 H2 0.9500 . ? C3 C4 1.4028(10) . ? C3 H3 0.9500 . ? C4 N1 1.3299(9) . ? C4 H4 0.9500 . ? C5 N3 1.4937(9) . ? C5 C6 1.5086(9) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C11 1.3952(10) . ? C6 C7 1.3988(9) . ? C7 C8 1.3955(9) . ? C7 H7 0.9500 . ? C8 C9 1.3966(10) . ? C8 C12 1.5075(9) . ? C9 C10 1.3905(10) . ? C9 H9 0.9500 . ? C10 C11 1.3949(10) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 N4 1.4935(8) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 N5 1.3181(9) . ? C13 N6 1.3566(8) . ? C13 N4 1.3720(8) . ? C14 N6 1.3208(9) . ? C14 C15 1.4067(11) . ? C14 H14 0.9500 . ? C15 C16 1.3656(10) . ? C15 H15 0.9500 . ? C16 N4 1.3603(9) . ? C16 H16 0.9500 . ? C17 F3 1.3233(12) . ? C17 F2 1.3304(11) . ? C17 F1 1.3358(13) . ? C17 S1 1.8300(10) . ? N2 H2A 0.8800 . ? N2 H2B 0.8800 . ? N5 H5C 0.8800 . ? N5 H5D 0.8800 . ? S1 O2 1.4391(6) . ? S1 O1 1.4469(6) . ? S1 O3 1.4502(6) . ? S2 O6 1.4450(10) . ? S2 O4 1.4484(9) . ? S2 O5 1.4512(7) . ? S2 C18 1.8263(8) . ? C18 F4 1.3294(11) . ? C18 F6 1.3330(11) . ? C18 F5 1.3412(11) . ? P1 F10 1.59(2) . ? P1 F9 1.604(15) . ? P1 F11 1.607(17) . ? P1 F7 1.631(14) . ? P1 F12 1.66(3) . ? P1 F8 1.665(13) . ? 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 N2 C1 N1 118.05(6) . . ? N2 C1 N3 120.09(6) . . ? N1 C1 N3 121.85(6) . . ? N3 C2 C3 120.50(6) . . ? N3 C2 H2 119.7 . . ? C3 C2 H2 119.7 . . ? C2 C3 C4 116.98(6) . . ? C2 C3 H3 121.5 . . ? C4 C3 H3 121.5 . . ? N1 C4 C3 123.17(6) . . ? N1 C4 H4 118.4 . . ? C3 C4 H4 118.4 . . ? N3 C5 C6 113.60(5) . . ? N3 C5 H5A 108.8 . . ? C6 C5 H5A 108.8 . . ? N3 C5 H5B 108.8 . . ? C6 C5 H5B 108.8 . . ? H5A C5 H5B 107.7 . . ? C11 C6 C7 119.89(6) . . ? C11 C6 C5 119.90(6) . . ? C7 C6 C5 120.11(6) . . ? C8 C7 C6 119.99(6) . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C7 C8 C9 119.72(6) . . ? C7 C8 C12 120.56(6) . . ? C9 C8 C12 119.61(6) . . ? C10 C9 C8 120.43(6) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C9 C10 C11 119.83(6) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? C10 C11 C6 120.14(6) . . ? C10 C11 H11 119.9 . . ? C6 C11 H11 119.9 . . ? N4 C12 C8 112.93(5) . . ? N4 C12 H12A 109.0 . . ? C8 C12 H12A 109.0 . . ? N4 C12 H12B 109.0 . . ? C8 C12 H12B 109.0 . . ? H12A C12 H12B 107.8 . . ? N5 C13 N6 118.24(6) . . ? N5 C13 N4 120.54(6) . . ? N6 C13 N4 121.20(6) . . ? N6 C14 C15 123.03(6) . . ? N6 C14 H14 118.5 . . ? C15 C14 H14 118.5 . . ? C16 C15 C14 116.89(6) . . ? C16 C15 H15 121.6 . . ? C14 C15 H15 121.6 . . ? N4 C16 C15 120.59(6) . . ? N4 C16 H16 119.7 . . ? C15 C16 H16 119.7 . . ? F3 C17 F2 108.65(9) . . ? F3 C17 F1 107.15(10) . . ? F2 C17 F1 107.70(9) . . ? F3 C17 S1 111.27(8) . . ? F2 C17 S1 111.39(7) . . ? F1 C17 S1 110.52(7) . . ? C4 N1 C1 117.90(6) . . ? C1 N2 H2A 120.0 . . ? C1 N2 H2B 120.0 . . ? H2A N2 H2B 120.0 . . ? C2 N3 C1 119.36(6) . . ? C2 N3 C5 121.88(5) . . ? C1 N3 C5 118.75(5) . . ? C16 N4 C13 119.30(5) . . ? C16 N4 C12 121.34(5) . . ? C13 N4 C12 119.28(5) . . ? C13 N5 H5C 120.0 . . ? C13 N5 H5D 120.0 . . ? H5C N5 H5D 120.0 . . ? C14 N6 C13 118.20(6) . . ? O2 S1 O1 114.92(4) . . ? O2 S1 O3 115.70(4) . . ? O1 S1 O3 113.41(4) . . ? O2 S1 C17 104.13(5) . . ? O1 S1 C17 103.46(4) . . ? O3 S1 C17 103.09(4) . . ? O6 S2 O4 115.93(7) . . ? O6 S2 O5 114.94(7) . . ? O4 S2 O5 113.86(5) . . ? O6 S2 C18 102.76(6) . . ? O4 S2 C18 103.71(5) . . ? O5 S2 C18 103.29(4) . . ? F4 C18 F6 108.10(8) . . ? F4 C18 F5 107.70(8) . . ? F6 C18 F5 107.35(7) . . ? F4 C18 S2 112.36(6) . . ? F6 C18 S2 110.69(7) . . ? F5 C18 S2 110.46(6) . . ? F10 P1 F9 89.9(11) . . ? F10 P1 F11 90.1(12) . . ? F9 P1 F11 92.8(8) . . ? F10 P1 F7 178.5(11) . . ? F9 P1 F7 90.0(8) . . ? F11 P1 F7 91.4(8) . . ? F10 P1 F12 86.5(14) . . ? F9 P1 F12 175.5(11) . . ? F11 P1 F12 84.4(12) . . ? F7 P1 F12 93.6(11) . . ? F10 P1 F8 89.3(11) . . ? F9 P1 F8 90.2(7) . . ? F11 P1 F8 176.9(8) . . ? F7 P1 F8 89.1(7) . . ? F12 P1 F8 92.5(11) . . ? 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 N3 C2 C3 C4 1.05(11) . . . . ? C2 C3 C4 N1 -3.17(12) . . . . ? N3 C5 C6 C11 73.48(8) . . . . ? N3 C5 C6 C7 -110.15(7) . . . . ? C11 C6 C7 C8 0.63(10) . . . . ? C5 C6 C7 C8 -175.74(6) . . . . ? C6 C7 C8 C9 -0.71(10) . . . . ? C6 C7 C8 C12 175.46(6) . . . . ? C7 C8 C9 C10 0.10(11) . . . . ? C12 C8 C9 C10 -176.11(7) . . . . ? C8 C9 C10 C11 0.59(11) . . . . ? C9 C10 C11 C6 -0.67(11) . . . . ? C7 C6 C11 C10 0.06(11) . . . . ? C5 C6 C11 C10 176.44(7) . . . . ? C7 C8 C12 N4 122.46(7) . . . . ? C9 C8 C12 N4 -61.37(9) . . . . ? N6 C14 C15 C16 5.26(13) . . . . ? C14 C15 C16 N4 -2.50(12) . . . . ? C3 C4 N1 C1 1.00(12) . . . . ? N2 C1 N1 C4 -177.32(7) . . . . ? N3 C1 N1 C4 3.36(11) . . . . ? C3 C2 N3 C1 3.03(10) . . . . ? C3 C2 N3 C5 -177.82(7) . . . . ? N2 C1 N3 C2 175.29(7) . . . . ? N1 C1 N3 C2 -5.41(10) . . . . ? N2 C1 N3 C5 -3.89(10) . . . . ? N1 C1 N3 C5 175.41(7) . . . . ? C6 C5 N3 C2 18.19(10) . . . . ? C6 C5 N3 C1 -162.65(6) . . . . ? C15 C16 N4 C13 -4.91(11) . . . . ? C15 C16 N4 C12 178.37(7) . . . . ? N5 C13 N4 C16 -171.25(7) . . . . ? N6 C13 N4 C16 10.26(10) . . . . ? N5 C13 N4 C12 5.53(10) . . . . ? N6 C13 N4 C12 -172.96(7) . . . . ? C8 C12 N4 C16 -29.02(9) . . . . ? C8 C12 N4 C13 154.26(6) . . . . ? C15 C14 N6 C13 -0.26(12) . . . . ? N5 C13 N6 C14 173.88(7) . . . . ? N4 C13 N6 C14 -7.59(11) . . . . ? F3 C17 S1 O2 -56.92(8) . . . . ? F2 C17 S1 O2 64.48(8) . . . . ? F1 C17 S1 O2 -175.83(7) . . . . ? F3 C17 S1 O1 -177.38(8) . . . . ? F2 C17 S1 O1 -55.98(9) . . . . ? F1 C17 S1 O1 63.70(8) . . . . ? F3 C17 S1 O3 64.26(8) . . . . ? F2 C17 S1 O3 -174.34(7) . . . . ? F1 C17 S1 O3 -54.66(8) . . . . ? O6 S2 C18 F4 178.33(9) . . . . ? O4 S2 C18 F4 57.22(8) . . . . ? O5 S2 C18 F4 -61.82(8) . . . . ? O6 S2 C18 F6 57.38(9) . . . . ? O4 S2 C18 F6 -63.73(8) . . . . ? O5 S2 C18 F6 177.23(6) . . . . ? O6 S2 C18 F5 -61.37(9) . . . . ? O4 S2 C18 F5 177.52(7) . . . . ? O5 S2 C18 F5 58.47(8) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2A N6 0.88 2.28 3.1499(8) 171.7 1_666 N2 H2B O3 0.88 2.21 3.0602(9) 162.0 2_666 N2 H2B S1 0.88 2.86 3.5276(6) 133.9 2_666 N5 H5C O1 0.88 1.95 2.8205(8) 169.4 2 N5 H5D O5 0.88 2.05 2.8436(9) 149.0 1_455 N5 H5D F11 0.88 2.11 2.905(18) 150.1 1_455 _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 40.05 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.577 _refine_diff_density_min -0.384 _refine_diff_density_rms 0.061 # Attachment '28.CIF' data_lj128sad _database_code_depnum_ccdc_archive 'CCDC 743959' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C5 H8 N3, N O3' _chemical_formula_sum 'C5 H8 N4 O3' _chemical_formula_weight 172.15 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' _symmetry_cell_setting Trigonal _symmetry_space_group_name_H-M P32 _symmetry_space_group_name_Hall 'P 32' _Intl_tables_symmetry_no 145 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+2/3' '-x+y, -x, z+1/3' _cell_length_a 6.1596(7) _cell_length_b 6.1596(7) _cell_length_c 16.966(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 557.46(16) _cell_formula_units_Z 3 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4414 _cell_measurement_theta_min 3.603 _cell_measurement_theta_max 28.281 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.600 _exptl_crystal_size_mid 0.570 _exptl_crystal_size_min 0.560 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.538 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 270 _exptl_absorpt_coefficient_mu 0.128 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.834 _exptl_absorpt_correction_T_max 0.931 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; The crystal was coated in Exxon Paratone N hydrocarbon oil and mounted on a thin mohair fibre attached to a copper pin. Upon mounting on the diffractometer, the crystal was quenched to 150(K) under a cold nitrogen gas stream supplied by an Oxford Cryosystems Cryostream. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1000 CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 88 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 16 _diffrn_reflns_number 5431 _diffrn_reflns_av_R_equivalents 0.0190 _diffrn_reflns_av_sigmaI/netI 0.0162 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.60 _diffrn_reflns_theta_max 28.29 _reflns_number_total 1771 _reflns_number_gt 1740 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker,1995)' _computing_cell_refinement 'SAINT (Bruker,1995)' _computing_data_reduction 'SAINT and XPREP (Bruker, 1995)' _computing_structure_solution 'SIR97 (Altomare, et. al. 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997), WINGX-32 (Farrugia, 1999)' _computing_publication_material 'enCIFer 1.1 (CCDC, 2005)' _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^)+(0.0509P)^2^+0.0552P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881 863 Friedel pairs' _refine_ls_abs_structure_Flack 0.074(1) _refine_ls_number_reflns 1771 _refine_ls_number_parameters 116 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0270 _refine_ls_R_factor_gt 0.0266 _refine_ls_wR_factor_ref 0.0690 _refine_ls_wR_factor_gt 0.0685 _refine_ls_goodness_of_fit_ref 0.983 _refine_ls_restrained_S_all 0.982 _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 0.87653(19) 1.0515(2) 0.45601(6) 0.0198(2) Uani 1 1 d . . . C2 C 0.84052(19) 0.9819(2) 0.53659(6) 0.0200(2) Uani 1 1 d . . . H2 H 0.9079 1.1063 0.5766 0.024 Uiso 1 1 calc R . . C3 C 0.6176(2) 0.5598(2) 0.49946(7) 0.0232(2) Uani 1 1 d . . . H3 H 0.5264 0.3871 0.5130 0.028 Uiso 1 1 calc R . . C4 C 0.6599(2) 0.6369(2) 0.42181(7) 0.0249(2) Uani 1 1 d . . . H4 H 0.5953 0.5115 0.3821 0.030 Uiso 1 1 calc R . . C5 C 0.6645(2) 0.6667(2) 0.63976(7) 0.0264(2) Uani 1 1 d . . . H5A H 0.8245 0.7415 0.6681 0.040 Uiso 1 1 calc R . . H5B H 0.5804 0.4837 0.6441 0.040 Uiso 1 1 calc R . . H5C H 0.5578 0.7263 0.6628 0.040 Uiso 1 1 calc R . . N1 N 0.78529(18) 0.87523(18) 0.39895(5) 0.0224(2) Uani 1 1 d . . . N2 N 0.71126(16) 0.74043(17) 0.55540(5) 0.01972(19) Uani 1 1 d . . . N3 N 1.0033(2) 1.29276(19) 0.43481(7) 0.0272(2) Uani 1 1 d . . . N4 N 0.27151(17) 0.84219(18) 0.55295(5) 0.0212(2) Uani 1 1 d . . . O1 O 0.28518(18) 0.87747(19) 0.48034(5) 0.0317(2) Uani 1 1 d . . . O2 O 0.38799(19) 1.02401(16) 0.59906(5) 0.0330(2) Uani 1 1 d . . . O3 O 0.14361(16) 0.62536(17) 0.58022(5) 0.02875(19) Uani 1 1 d . . . H1N H 1.024(3) 1.329(3) 0.3878(14) 0.035 Uiso 1 1 d . . . H2N H 1.050(3) 1.410(4) 0.4699(11) 0.035 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0173(4) 0.0223(5) 0.0210(5) -0.0010(4) -0.0004(3) 0.0107(4) C2 0.0189(5) 0.0221(5) 0.0194(5) -0.0030(4) -0.0017(4) 0.0106(4) C3 0.0227(5) 0.0200(5) 0.0255(6) -0.0006(4) -0.0016(4) 0.0095(4) C4 0.0255(5) 0.0230(5) 0.0249(6) -0.0050(4) -0.0038(4) 0.0112(4) C5 0.0282(6) 0.0355(6) 0.0173(6) 0.0055(4) 0.0014(4) 0.0173(5) N1 0.0236(4) 0.0233(4) 0.0192(4) -0.0015(3) -0.0013(3) 0.0108(4) N2 0.0173(4) 0.0246(4) 0.0187(4) 0.0014(3) -0.0004(3) 0.0116(4) N3 0.0317(5) 0.0206(5) 0.0234(5) 0.0000(4) 0.0002(4) 0.0085(4) N4 0.0222(4) 0.0268(4) 0.0204(4) 0.0002(3) 0.0010(3) 0.0165(4) O1 0.0365(5) 0.0448(5) 0.0184(4) 0.0035(4) 0.0007(3) 0.0236(4) O2 0.0448(5) 0.0259(4) 0.0270(4) -0.0058(3) 0.0012(4) 0.0168(4) O3 0.0279(4) 0.0255(4) 0.0309(4) 0.0036(3) 0.0019(3) 0.0118(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 C1 N3 1.3370(15) . ? C1 N1 1.3496(13) . ? C1 C2 1.4167(15) . ? C2 N2 1.3281(14) . ? C2 H2 0.9500 . ? C3 N2 1.3525(15) . ? C3 C4 1.3804(17) . ? C3 H3 0.9500 . ? C4 N1 1.3295(14) . ? C4 H4 0.9500 . ? C5 N2 1.4857(15) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? N3 H1N 0.82(2) . ? N3 H2N 0.867(19) . ? N4 O1 1.2464(12) . ? N4 O3 1.2515(14) . ? N4 O2 1.2560(13) . ? 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 N3 C1 N1 118.56(10) . . ? N3 C1 C2 120.79(10) . . ? N1 C1 C2 120.65(10) . . ? N2 C2 C1 119.08(9) . . ? N2 C2 H2 120.5 . . ? C1 C2 H2 120.5 . . ? N2 C3 C4 117.20(10) . . ? N2 C3 H3 121.4 . . ? C4 C3 H3 121.4 . . ? N1 C4 C3 124.32(10) . . ? N1 C4 H4 117.8 . . ? C3 C4 H4 117.8 . . ? N2 C5 H5A 109.5 . . ? N2 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N2 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 N1 C1 117.20(10) . . ? C2 N2 C3 121.53(10) . . ? C2 N2 C5 119.33(9) . . ? C3 N2 C5 119.13(9) . . ? C1 N3 H1N 119.2(13) . . ? C1 N3 H2N 120.5(12) . . ? H1N N3 H2N 120.0(17) . . ? O1 N4 O3 120.21(10) . . ? O1 N4 O2 120.10(10) . . ? O3 N4 O2 119.69(9) . . ? 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 N3 C1 C2 N2 179.29(9) . . . . ? N1 C1 C2 N2 -1.30(14) . . . . ? N2 C3 C4 N1 -0.16(17) . . . . ? C3 C4 N1 C1 0.12(16) . . . . ? N3 C1 N1 C4 -179.97(10) . . . . ? C2 C1 N1 C4 0.60(15) . . . . ? C1 C2 N2 C3 1.27(14) . . . . ? C1 C2 N2 C5 -177.67(9) . . . . ? C4 C3 N2 C2 -0.57(15) . . . . ? C4 C3 N2 C5 178.37(10) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3 H1N O2 0.82(2) 2.12(2) 2.9195(16) 165.4(18) 2_774 N3 H2N O3 0.867(19) 2.198(19) 3.0431(15) 165.0(17) 1_665 N3 H2N O1 0.867(19) 2.500(19) 3.2139(15) 140.1(15) 1_665 N3 H2N N4 0.867(19) 2.702(19) 3.5509(15) 166.5(16) 1_665 _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.164 _refine_diff_density_min -0.270 _refine_diff_density_rms 0.057