# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Ennio Zangrando' _publ_contact_author_email ezangrando@units.it loop_ _publ_author_name 'Diego Montagner' 'Ennio Zangrando' 'Giuseppe Borsato' 'Vittorio Lucchini' 'Bruno Longato' data_1b _database_code_depnum_ccdc_archive 'CCDC 811783' #TrackingRef 'cif_data.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C48 H41 N4 O P2 Pt 1+, N O3 1-, C4 H10 O)' _chemical_formula_sum 'C52 H51 N5 O5 P2 Pt' _chemical_formula_weight 1083.01 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Pt Pt -1.7033 8.3905 '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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 12.795(2) _cell_length_b 14.002(2) _cell_length_c 14.667(3) _cell_angle_alpha 114.857(9) _cell_angle_beta 94.249(10) _cell_angle_gamma 95.843(10) _cell_volume 2351.9(7) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.529 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1092 _exptl_absorpt_coefficient_mu 3.105 _exptl_absorpt_correction_type refdelf _exptl_absorpt_correction_T_min 0.3228 _exptl_absorpt_correction_T_max 0.4955 _exptl_absorpt_process_details ; Parkin S,Moezzi B & Hope H, (1995) J. Appl. Cryst. 28, 53-56 Cubic fit to sin(theta)/lambda - 24 parameters ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'image plate dip1030' _diffrn_measurement_method 'laser scanner' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 34811 _diffrn_reflns_av_R_equivalents 0.0550 _diffrn_reflns_av_sigmaI/netI 0.0640 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.54 _diffrn_reflns_theta_max 27.88 _reflns_number_total 10835 _reflns_number_gt 8219 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Nonius Xpress' _computing_cell_refinement 'Denzo (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELX97 (Sheldrick, 1998)' _computing_structure_refinement 'SHELX97 (Sheldrick, 1998)' _computing_molecular_graphics 'Ortep3/windows (Farrugia,1997)' _computing_publication_material 'Wingx 1.70.00 (Farrugia, 1999)' _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^ > 2\s(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^)+(0.0520P)^2^+0.0000P] 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 10835 _refine_ls_number_parameters 587 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0536 _refine_ls_R_factor_gt 0.0400 _refine_ls_wR_factor_ref 0.0987 _refine_ls_wR_factor_gt 0.0943 _refine_ls_goodness_of_fit_ref 0.949 _refine_ls_restrained_S_all 0.949 _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 Pt Pt 0.683876(13) 0.238253(14) 0.407241(14) 0.04308(7) Uani 1 1 d . . . P1 P 0.80489(9) 0.14002(9) 0.43511(10) 0.0456(3) Uani 1 1 d . . . P2 P 0.61694(9) 0.12502(10) 0.24328(9) 0.0463(3) Uani 1 1 d . . . N1 N 0.8857(3) 0.4836(3) 0.6584(3) 0.0508(9) Uani 1 1 d . . . N2 N 0.5595(3) 0.3214(3) 0.4126(3) 0.0468(8) Uani 1 1 d . . . H2 H 0.5357 0.3284 0.3597 0.056 Uiso 1 1 calc R . . N3 N 0.7375(3) 0.3679(3) 0.5450(3) 0.0443(8) Uani 1 1 d . . . N4 N 0.5642(3) 0.3980(3) 0.5913(3) 0.0502(9) Uani 1 1 d . . . O2 O 0.9027(2) 0.3763(3) 0.4947(3) 0.0525(8) Uani 1 1 d . . . C1 C 0.9993(4) 0.5250(4) 0.6776(4) 0.0595(13) Uani 1 1 d . . . H1A H 1.0165 0.5790 0.7460 0.089 Uiso 1 1 calc R . . H1B H 1.0158 0.5550 0.6314 0.089 Uiso 1 1 calc R . . H1C H 1.0397 0.4682 0.6680 0.089 Uiso 1 1 calc R . . C2 C 0.8452(4) 0.4073(4) 0.5619(4) 0.0489(11) Uani 1 1 d . . . C3 C 0.5163(4) 0.3639(3) 0.4963(4) 0.0470(10) Uani 1 1 d . . . C4 C 0.6710(4) 0.4150(4) 0.6119(4) 0.0489(11) Uani 1 1 d . . . C5 C 0.7164(4) 0.4879(4) 0.7118(4) 0.0575(12) Uani 1 1 d . . . H5 H 0.6737 0.5137 0.7630 0.069 Uiso 1 1 calc R . . C6 C 0.8208(4) 0.5188(4) 0.7314(4) 0.0560(12) Uani 1 1 d . . . H6 H 0.8502 0.5659 0.7970 0.067 Uiso 1 1 calc R . . C7 C 0.4008(3) 0.3769(4) 0.4906(4) 0.0478(10) Uani 1 1 d . . . C8 C 0.3333(4) 0.3249(4) 0.4002(4) 0.0584(13) Uani 1 1 d . . . H8 H 0.3602 0.2857 0.3406 0.070 Uiso 1 1 calc R . . C9 C 0.2259(4) 0.3312(5) 0.3985(5) 0.0674(15) Uani 1 1 d . . . H9 H 0.1813 0.2970 0.3374 0.081 Uiso 1 1 calc R . . C10 C 0.1847(4) 0.3875(5) 0.4861(5) 0.0662(15) Uani 1 1 d . . . H10 H 0.1121 0.3894 0.4848 0.079 Uiso 1 1 calc R . . C11 C 0.2510(4) 0.4412(5) 0.5755(5) 0.0667(15) Uani 1 1 d . . . H11 H 0.2236 0.4811 0.6347 0.080 Uiso 1 1 calc R . . C12 C 0.3591(4) 0.4359(4) 0.5780(4) 0.0575(12) Uani 1 1 d . . . H12 H 0.4036 0.4723 0.6389 0.069 Uiso 1 1 calc R . . C13 C 0.7360(4) 0.0174(4) 0.4345(4) 0.0478(10) Uani 1 1 d . . . C14 C 0.7907(4) -0.0479(4) 0.4654(5) 0.0627(14) Uani 1 1 d . . . H14 H 0.8630 -0.0301 0.4877 0.075 Uiso 1 1 calc R . . C15 C 0.7333(5) -0.1414(5) 0.4618(5) 0.0729(16) Uani 1 1 d . . . H15 H 0.7690 -0.1865 0.4801 0.088 Uiso 1 1 calc R . . C16 C 0.6263(5) -0.1670(5) 0.4318(5) 0.0683(15) Uani 1 1 d . . . H16 H 0.5902 -0.2302 0.4274 0.082 Uiso 1 1 calc R . . C17 C 0.5730(5) -0.0984(5) 0.4084(5) 0.0683(15) Uani 1 1 d . . . H17 H 0.4998 -0.1130 0.3912 0.082 Uiso 1 1 calc R . . C18 C 0.6291(4) -0.0067(4) 0.4104(4) 0.0587(13) Uani 1 1 d . . . H18 H 0.5921 0.0394 0.3948 0.070 Uiso 1 1 calc R . . C19 C 0.8765(4) 0.1997(4) 0.5626(4) 0.0510(11) Uani 1 1 d . . . C20 C 0.9867(4) 0.2222(4) 0.5803(5) 0.0647(14) Uani 1 1 d . . . H20 H 1.0257 0.2083 0.5262 0.078 Uiso 1 1 calc R . . C21 C 1.0388(5) 0.2659(5) 0.6800(5) 0.0736(17) Uani 1 1 d . . . H21 H 1.1123 0.2800 0.6925 0.088 Uiso 1 1 calc R . . C22 C 0.9763(6) 0.2885(5) 0.7620(5) 0.0788(19) Uani 1 1 d . . . H22 H 1.0095 0.3175 0.8284 0.095 Uiso 1 1 calc R . . C23 C 0.8704(6) 0.2680(5) 0.7431(5) 0.0769(18) Uani 1 1 d . . . H23 H 0.8308 0.2839 0.7970 0.092 Uiso 1 1 calc R . . C24 C 0.8191(5) 0.2238(4) 0.6454(4) 0.0605(13) Uani 1 1 d . . . H24 H 0.7455 0.2098 0.6342 0.073 Uiso 1 1 calc R . . C25 C 0.9044(4) 0.1045(4) 0.3506(4) 0.0516(11) Uani 1 1 d . . . C26 C 0.9287(4) 0.1696(4) 0.3022(4) 0.0578(12) Uani 1 1 d . . . H26 H 0.8936 0.2278 0.3136 0.069 Uiso 1 1 calc R . . C27 C 1.0061(5) 0.1469(5) 0.2365(4) 0.0676(14) Uani 1 1 d . . . H27 H 1.0205 0.1884 0.2021 0.081 Uiso 1 1 calc R . . C28 C 1.0613(4) 0.0629(6) 0.2226(5) 0.0751(17) Uani 1 1 d . . . H28 H 1.1138 0.0487 0.1801 0.090 Uiso 1 1 calc R . . C29 C 1.0382(5) 0.0005(5) 0.2722(5) 0.0735(16) Uani 1 1 d . . . H29 H 1.0764 -0.0551 0.2638 0.088 Uiso 1 1 calc R . . C30 C 0.9598(4) 0.0185(5) 0.3338(5) 0.0666(14) Uani 1 1 d . . . H30 H 0.9434 -0.0263 0.3645 0.080 Uiso 1 1 calc R . . C31 C 0.7016(4) 0.0427(4) 0.1582(4) 0.0567(12) Uani 1 1 d . . . C32 C 0.7466(5) 0.0725(5) 0.0891(5) 0.0741(16) Uani 1 1 d . . . H32 H 0.7310 0.1340 0.0847 0.089 Uiso 1 1 calc R . . C33 C 0.8137(6) 0.0128(7) 0.0269(5) 0.092(2) Uani 1 1 d . . . H33 H 0.8440 0.0343 -0.0184 0.111 Uiso 1 1 calc R . . C34 C 0.8353(6) -0.0769(7) 0.0319(6) 0.089(2) Uani 1 1 d . . . H34 H 0.8787 -0.1183 -0.0121 0.107 Uiso 1 1 calc R . . C35 C 0.7955(5) -0.1087(5) 0.0996(6) 0.0826(19) Uani 1 1 d . . . H35 H 0.8139 -0.1695 0.1039 0.099 Uiso 1 1 calc R . . C36 C 0.7255(5) -0.0481(5) 0.1639(5) 0.0725(16) Uani 1 1 d . . . H36 H 0.6962 -0.0698 0.2095 0.087 Uiso 1 1 calc R . . C37 C 0.4954(4) 0.0356(4) 0.2239(4) 0.0498(11) Uani 1 1 d . . . C38 C 0.4667(5) -0.0552(5) 0.1318(4) 0.0639(14) Uani 1 1 d . . . H38 H 0.5122 -0.0725 0.0825 0.077 Uiso 1 1 calc R . . C39 C 0.3705(5) -0.1193(5) 0.1144(5) 0.0772(17) Uani 1 1 d . . . H39 H 0.3528 -0.1813 0.0546 0.093 Uiso 1 1 calc R . . C40 C 0.3018(5) -0.0918(5) 0.1846(5) 0.0706(16) Uani 1 1 d . . . H40 H 0.2357 -0.1330 0.1706 0.085 Uiso 1 1 calc R . . C41 C 0.3287(4) -0.0036(5) 0.2761(5) 0.0645(14) Uani 1 1 d . . . H41 H 0.2825 0.0129 0.3248 0.077 Uiso 1 1 calc R . . C42 C 0.4251(4) 0.0603(4) 0.2950(4) 0.0539(11) Uani 1 1 d . . . H42 H 0.4429 0.1206 0.3563 0.065 Uiso 1 1 calc R . . C43 C 0.5764(4) 0.2126(4) 0.1873(4) 0.0531(11) Uani 1 1 d . . . C44 C 0.4735(5) 0.1989(4) 0.1403(4) 0.0624(13) Uani 1 1 d . . . H44 H 0.4236 0.1430 0.1348 0.075 Uiso 1 1 calc R . . C45 C 0.4465(6) 0.2694(6) 0.1020(5) 0.0811(19) Uani 1 1 d . . . H45 H 0.3781 0.2606 0.0705 0.097 Uiso 1 1 calc R . . C46 C 0.5194(7) 0.3516(6) 0.1100(5) 0.090(2) Uani 1 1 d . . . H46 H 0.4999 0.3981 0.0837 0.108 Uiso 1 1 calc R . . C47 C 0.6219(7) 0.3672(5) 0.1565(5) 0.084(2) Uani 1 1 d . . . H47 H 0.6711 0.4230 0.1608 0.101 Uiso 1 1 calc R . . C48 C 0.6500(5) 0.2979(5) 0.1968(5) 0.0671(14) Uani 1 1 d . . . H48 H 0.7180 0.3085 0.2300 0.080 Uiso 1 1 calc R . . N5 N 0.9498(6) 0.2726(5) 0.0358(5) 0.0919(18) Uani 1 1 d . . . O11 O 0.8720(7) 0.2916(7) 0.0882(8) 0.175(3) Uani 1 1 d . . . O12 O 0.9272(7) 0.2279(7) -0.0510(5) 0.177(4) Uani 1 1 d . . . O13 O 1.0327(6) 0.2915(5) 0.0807(6) 0.164(3) Uani 1 1 d . . . O1 O 0.3487(7) 0.4245(6) 0.9185(6) 0.148(3) Uani 1 1 d . . . C51 C 0.2436(10) 0.4204(11) 0.9434(13) 0.172(5) Uani 1 1 d . . . H51A H 0.1955 0.3921 0.8808 0.207 Uiso 1 1 calc R . . H51B H 0.2344 0.3697 0.9723 0.207 Uiso 1 1 calc R . . C52 C 0.3876(12) 0.3337(9) 0.8506(11) 0.173(5) Uani 1 1 d . . . H52A H 0.3451 0.3072 0.7850 0.207 Uiso 1 1 calc R . . H52B H 0.3781 0.2789 0.8745 0.207 Uiso 1 1 calc R . . C53 C 0.2119(14) 0.5140(12) 1.0094(12) 0.206(7) Uani 1 1 d . . . H53A H 0.1404 0.4995 1.0211 0.310 Uiso 1 1 calc R . . H53B H 0.2155 0.5640 0.9803 0.310 Uiso 1 1 calc R . . H53C H 0.2579 0.5434 1.0725 0.310 Uiso 1 1 calc R . . C54 C 0.5002(12) 0.3508(9) 0.8370(8) 0.158(5) Uani 1 1 d . . . H54A H 0.5203 0.2846 0.7920 0.237 Uiso 1 1 calc R . . H54B H 0.5434 0.3778 0.9015 0.237 Uiso 1 1 calc R . . H54C H 0.5100 0.4012 0.8088 0.237 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 Pt 0.04379(10) 0.04241(10) 0.04255(11) 0.01696(7) 0.00702(7) 0.00924(6) P1 0.0434(6) 0.0447(6) 0.0493(7) 0.0197(5) 0.0071(5) 0.0110(5) P2 0.0477(6) 0.0470(6) 0.0408(7) 0.0153(5) 0.0064(5) 0.0086(5) N1 0.041(2) 0.055(2) 0.051(2) 0.018(2) 0.0055(17) 0.0055(17) N2 0.047(2) 0.046(2) 0.045(2) 0.0162(18) 0.0066(16) 0.0096(16) N3 0.0339(17) 0.0450(19) 0.051(2) 0.0166(17) 0.0108(16) 0.0093(14) N4 0.045(2) 0.054(2) 0.047(2) 0.0170(19) 0.0074(17) 0.0085(16) O2 0.0501(18) 0.0527(19) 0.052(2) 0.0189(16) 0.0132(15) 0.0100(14) C1 0.047(3) 0.063(3) 0.058(3) 0.018(3) -0.002(2) 0.002(2) C2 0.053(3) 0.042(2) 0.051(3) 0.020(2) 0.002(2) 0.0059(19) C3 0.049(2) 0.038(2) 0.054(3) 0.020(2) 0.007(2) 0.0072(18) C4 0.045(2) 0.051(3) 0.052(3) 0.022(2) 0.009(2) 0.0103(19) C5 0.053(3) 0.063(3) 0.045(3) 0.013(2) 0.008(2) 0.007(2) C6 0.059(3) 0.055(3) 0.046(3) 0.013(2) 0.005(2) 0.013(2) C7 0.043(2) 0.044(2) 0.060(3) 0.024(2) 0.007(2) 0.0103(18) C8 0.051(3) 0.057(3) 0.062(3) 0.023(3) 0.002(2) 0.003(2) C9 0.053(3) 0.067(3) 0.075(4) 0.026(3) -0.006(3) 0.006(2) C10 0.055(3) 0.064(3) 0.087(5) 0.037(3) 0.013(3) 0.019(3) C11 0.062(3) 0.064(3) 0.076(4) 0.027(3) 0.019(3) 0.022(3) C12 0.053(3) 0.058(3) 0.061(3) 0.024(3) 0.013(2) 0.015(2) C13 0.053(3) 0.048(2) 0.050(3) 0.025(2) 0.012(2) 0.015(2) C14 0.062(3) 0.064(3) 0.070(4) 0.035(3) 0.011(3) 0.019(3) C15 0.092(4) 0.056(3) 0.086(5) 0.042(3) 0.020(3) 0.025(3) C16 0.089(4) 0.056(3) 0.069(4) 0.035(3) 0.019(3) 0.008(3) C17 0.060(3) 0.070(4) 0.078(4) 0.040(3) 0.000(3) -0.005(3) C18 0.060(3) 0.058(3) 0.066(3) 0.035(3) 0.006(2) 0.005(2) C19 0.053(3) 0.052(3) 0.051(3) 0.025(2) 0.002(2) 0.011(2) C20 0.060(3) 0.064(3) 0.070(4) 0.030(3) 0.000(3) 0.011(2) C21 0.062(3) 0.074(4) 0.077(4) 0.029(3) -0.012(3) 0.006(3) C22 0.107(5) 0.067(4) 0.053(4) 0.021(3) -0.019(4) 0.012(3) C23 0.110(5) 0.065(4) 0.054(4) 0.027(3) 0.005(3) 0.004(3) C24 0.064(3) 0.058(3) 0.058(3) 0.024(3) 0.008(3) 0.007(2) C25 0.046(2) 0.056(3) 0.055(3) 0.023(2) 0.011(2) 0.016(2) C26 0.051(3) 0.062(3) 0.053(3) 0.018(3) 0.004(2) 0.008(2) C27 0.068(3) 0.080(4) 0.054(3) 0.029(3) 0.012(3) 0.009(3) C28 0.059(3) 0.098(5) 0.063(4) 0.023(4) 0.025(3) 0.022(3) C29 0.064(3) 0.080(4) 0.077(4) 0.026(3) 0.028(3) 0.033(3) C30 0.066(3) 0.066(3) 0.077(4) 0.034(3) 0.022(3) 0.026(3) C31 0.054(3) 0.065(3) 0.045(3) 0.016(2) 0.007(2) 0.017(2) C32 0.082(4) 0.084(4) 0.053(4) 0.022(3) 0.020(3) 0.021(3) C33 0.096(5) 0.104(6) 0.064(4) 0.018(4) 0.035(4) 0.027(4) C34 0.077(4) 0.105(6) 0.066(4) 0.015(4) 0.016(3) 0.025(4) C35 0.078(4) 0.071(4) 0.085(5) 0.017(4) 0.004(4) 0.031(3) C36 0.083(4) 0.068(4) 0.058(4) 0.016(3) 0.008(3) 0.024(3) C37 0.046(2) 0.050(3) 0.050(3) 0.019(2) 0.006(2) 0.0090(19) C38 0.065(3) 0.067(3) 0.050(3) 0.017(3) 0.009(3) 0.005(3) C39 0.083(4) 0.064(4) 0.062(4) 0.011(3) -0.003(3) -0.008(3) C40 0.058(3) 0.068(4) 0.072(4) 0.024(3) -0.003(3) -0.011(3) C41 0.048(3) 0.077(4) 0.063(4) 0.026(3) 0.011(2) 0.002(2) C42 0.053(3) 0.054(3) 0.053(3) 0.020(2) 0.009(2) 0.012(2) C43 0.061(3) 0.050(3) 0.043(3) 0.015(2) 0.006(2) 0.009(2) C44 0.075(3) 0.055(3) 0.054(3) 0.019(3) 0.002(3) 0.017(2) C45 0.105(5) 0.077(4) 0.062(4) 0.029(3) -0.002(3) 0.032(4) C46 0.145(7) 0.073(4) 0.059(4) 0.032(3) 0.012(4) 0.038(4) C47 0.132(6) 0.062(4) 0.065(4) 0.033(3) 0.020(4) 0.010(4) C48 0.081(4) 0.062(3) 0.056(3) 0.024(3) 0.006(3) 0.009(3) N5 0.087(4) 0.090(4) 0.072(4) 0.016(3) -0.013(3) -0.002(3) O11 0.162(7) 0.169(7) 0.189(9) 0.067(7) 0.068(6) 0.021(6) O12 0.203(8) 0.206(8) 0.079(5) 0.044(5) -0.046(5) -0.033(6) O13 0.132(6) 0.128(5) 0.135(6) -0.028(4) -0.045(5) 0.030(4) O1 0.184(8) 0.116(5) 0.134(6) 0.047(5) 0.027(6) 0.007(5) C51 0.121(10) 0.143(11) 0.220(16) 0.060(11) 0.004(10) -0.022(8) C52 0.228(15) 0.087(7) 0.153(12) -0.003(7) 0.058(11) 0.025(8) C53 0.30(2) 0.169(13) 0.182(15) 0.074(12) 0.130(14) 0.090(13) C54 0.253(16) 0.116(8) 0.097(8) 0.038(6) 0.046(9) 0.010(9) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 Pt N2 2.052(4) . ? Pt N3 2.074(4) . ? Pt P2 2.2898(13) . ? Pt P1 2.2955(12) . ? P1 C25 1.803(5) . ? P1 C19 1.819(5) . ? P1 C13 1.845(5) . ? P2 C31 1.818(5) . ? P2 C37 1.819(5) . ? P2 C43 1.833(5) . ? N1 C6 1.360(7) . ? N1 C2 1.386(6) . ? N1 C1 1.469(6) . ? N2 C3 1.312(6) . ? N3 C4 1.347(6) . ? N3 C2 1.395(6) . ? N4 C3 1.342(6) . ? N4 C4 1.351(6) . ? O2 C2 1.231(6) . ? C3 C7 1.507(6) . ? C4 C5 1.423(7) . ? C5 C6 1.332(7) . ? C7 C12 1.384(7) . ? C7 C8 1.387(7) . ? C8 C9 1.385(7) . ? C9 C10 1.373(9) . ? C10 C11 1.372(8) . ? C11 C12 1.392(7) . ? C13 C18 1.358(7) . ? C13 C14 1.400(7) . ? C14 C15 1.413(8) . ? C15 C16 1.368(8) . ? C16 C17 1.373(8) . ? C17 C18 1.393(7) . ? C19 C20 1.393(7) . ? C19 C24 1.402(8) . ? C20 C21 1.406(8) . ? C21 C22 1.436(10) . ? C22 C23 1.339(10) . ? C23 C24 1.379(8) . ? C25 C26 1.396(7) . ? C25 C30 1.401(7) . ? C26 C27 1.399(8) . ? C27 C28 1.383(9) . ? C28 C29 1.377(9) . ? C29 C30 1.371(8) . ? C31 C36 1.372(8) . ? C31 C32 1.388(8) . ? C32 C33 1.376(9) . ? C33 C34 1.343(10) . ? C34 C35 1.358(11) . ? C35 C36 1.421(9) . ? C37 C42 1.384(7) . ? C37 C38 1.401(7) . ? C38 C39 1.387(8) . ? C39 C40 1.360(9) . ? C40 C41 1.377(8) . ? C41 C42 1.383(7) . ? C43 C48 1.395(8) . ? C43 C44 1.395(7) . ? C44 C45 1.385(8) . ? C45 C46 1.364(11) . ? C46 C47 1.384(10) . ? C47 C48 1.394(8) . ? N5 O13 1.149(8) . ? N5 O12 1.156(8) . ? N5 O11 1.284(10) . ? O1 C52 1.412(12) . ? O1 C51 1.422(14) . ? C51 C53 1.385(16) . ? C52 C54 1.477(17) . ? 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 Pt N3 82.20(14) . . ? N2 Pt P2 88.48(11) . . ? N3 Pt P2 166.67(11) . . ? N2 Pt P1 165.21(12) . . ? N3 Pt P1 92.35(10) . . ? P2 Pt P1 98.92(5) . . ? C25 P1 C19 105.8(2) . . ? C25 P1 C13 108.5(2) . . ? C19 P1 C13 99.4(2) . . ? C25 P1 Pt 116.98(16) . . ? C19 P1 Pt 114.41(16) . . ? C13 P1 Pt 110.13(15) . . ? C31 P2 C37 104.8(2) . . ? C31 P2 C43 105.4(2) . . ? C37 P2 C43 103.2(2) . . ? C31 P2 Pt 120.18(17) . . ? C37 P2 Pt 116.98(17) . . ? C43 P2 Pt 104.41(16) . . ? C6 N1 C2 120.2(4) . . ? C6 N1 C1 122.0(4) . . ? C2 N1 C1 117.8(4) . . ? C3 N2 Pt 120.3(3) . . ? C4 N3 C2 121.8(4) . . ? C4 N3 Pt 121.9(3) . . ? C2 N3 Pt 116.2(3) . . ? C3 N4 C4 121.1(4) . . ? O2 C2 N1 120.8(4) . . ? O2 C2 N3 122.0(4) . . ? N1 C2 N3 117.2(4) . . ? N2 C3 N4 126.6(4) . . ? N2 C3 C7 119.7(4) . . ? N4 C3 C7 113.6(4) . . ? N3 C4 N4 124.9(5) . . ? N3 C4 C5 117.7(4) . . ? N4 C4 C5 117.4(4) . . ? C6 C5 C4 119.3(5) . . ? C5 C6 N1 122.1(5) . . ? C12 C7 C8 118.8(4) . . ? C12 C7 C3 119.7(4) . . ? C8 C7 C3 121.3(5) . . ? C9 C8 C7 120.3(5) . . ? C10 C9 C8 120.6(5) . . ? C11 C10 C9 119.7(5) . . ? C10 C11 C12 120.2(6) . . ? C7 C12 C11 120.4(5) . . ? C18 C13 C14 118.9(5) . . ? C18 C13 P1 119.7(3) . . ? C14 C13 P1 121.3(4) . . ? C13 C14 C15 118.4(5) . . ? C16 C15 C14 121.5(5) . . ? C15 C16 C17 119.2(5) . . ? C16 C17 C18 119.6(5) . . ? C13 C18 C17 122.1(5) . . ? C20 C19 C24 119.1(5) . . ? C20 C19 P1 121.9(4) . . ? C24 C19 P1 119.0(4) . . ? C19 C20 C21 119.9(6) . . ? C20 C21 C22 118.8(6) . . ? C23 C22 C21 120.1(6) . . ? C22 C23 C24 121.2(7) . . ? C23 C24 C19 120.8(6) . . ? C26 C25 C30 119.1(5) . . ? C26 C25 P1 117.0(4) . . ? C30 C25 P1 123.9(4) . . ? C25 C26 C27 119.7(5) . . ? C28 C27 C26 120.2(6) . . ? C29 C28 C27 119.6(6) . . ? C30 C29 C28 121.3(5) . . ? C29 C30 C25 120.0(6) . . ? C36 C31 C32 118.8(6) . . ? C36 C31 P2 120.4(5) . . ? C32 C31 P2 120.8(4) . . ? C33 C32 C31 121.2(7) . . ? C34 C33 C32 119.6(7) . . ? C33 C34 C35 121.8(7) . . ? C34 C35 C36 119.2(7) . . ? C31 C36 C35 119.4(7) . . ? C42 C37 C38 118.7(5) . . ? C42 C37 P2 121.1(4) . . ? C38 C37 P2 119.9(4) . . ? C39 C38 C37 119.9(6) . . ? C40 C39 C38 120.2(6) . . ? C39 C40 C41 120.9(5) . . ? C40 C41 C42 119.5(6) . . ? C41 C42 C37 120.8(5) . . ? C48 C43 C44 119.8(5) . . ? C48 C43 P2 118.3(4) . . ? C44 C43 P2 121.9(4) . . ? C45 C44 C43 119.4(6) . . ? C46 C45 C44 120.5(6) . . ? C45 C46 C47 121.3(6) . . ? C46 C47 C48 118.9(6) . . ? C47 C48 C43 120.0(6) . . ? O13 N5 O12 127.4(10) . . ? O13 N5 O11 116.2(9) . . ? O12 N5 O11 115.7(9) . . ? C52 O1 C51 122.3(10) . . ? C53 C51 O1 118.2(11) . . ? O1 C52 C54 115.3(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 N2 Pt P1 C25 176.8(4) . . . . ? N3 Pt P1 C25 -115.3(2) . . . . ? P2 Pt P1 C25 57.51(19) . . . . ? N2 Pt P1 C19 -58.6(4) . . . . ? N3 Pt P1 C19 9.2(2) . . . . ? P2 Pt P1 C19 -177.92(18) . . . . ? N2 Pt P1 C13 52.3(5) . . . . ? N3 Pt P1 C13 120.2(2) . . . . ? P2 Pt P1 C13 -66.98(18) . . . . ? N2 Pt P2 C31 160.1(2) . . . . ? N3 Pt P2 C31 114.7(5) . . . . ? P1 Pt P2 C31 -32.7(2) . . . . ? N2 Pt P2 C37 -70.9(2) . . . . ? N3 Pt P2 C37 -116.4(4) . . . . ? P1 Pt P2 C37 96.22(18) . . . . ? N2 Pt P2 C43 42.3(2) . . . . ? N3 Pt P2 C43 -3.1(5) . . . . ? P1 Pt P2 C43 -150.53(18) . . . . ? N3 Pt N2 C3 -45.4(3) . . . . ? P2 Pt N2 C3 144.1(3) . . . . ? P1 Pt N2 C3 23.6(7) . . . . ? N2 Pt N3 C4 38.3(4) . . . . ? P2 Pt N3 C4 84.3(6) . . . . ? P1 Pt N3 C4 -127.9(3) . . . . ? N2 Pt N3 C2 -138.1(3) . . . . ? P2 Pt N3 C2 -92.1(5) . . . . ? P1 Pt N3 C2 55.7(3) . . . . ? C6 N1 C2 O2 178.6(4) . . . . ? C1 N1 C2 O2 -0.5(7) . . . . ? C6 N1 C2 N3 -1.5(6) . . . . ? C1 N1 C2 N3 179.4(4) . . . . ? C4 N3 C2 O2 -167.5(4) . . . . ? Pt N3 C2 O2 8.9(6) . . . . ? C4 N3 C2 N1 12.6(6) . . . . ? Pt N3 C2 N1 -171.0(3) . . . . ? Pt N2 C3 N4 28.6(6) . . . . ? Pt N2 C3 C7 -150.6(3) . . . . ? C4 N4 C3 N2 16.0(7) . . . . ? C4 N4 C3 C7 -164.7(4) . . . . ? C2 N3 C4 N4 163.5(4) . . . . ? Pt N3 C4 N4 -12.7(6) . . . . ? C2 N3 C4 C5 -16.7(7) . . . . ? Pt N3 C4 C5 167.1(3) . . . . ? C3 N4 C4 N3 -24.5(7) . . . . ? C3 N4 C4 C5 155.7(4) . . . . ? N3 C4 C5 C6 10.0(7) . . . . ? N4 C4 C5 C6 -170.2(5) . . . . ? C4 C5 C6 N1 0.6(8) . . . . ? C2 N1 C6 C5 -4.8(8) . . . . ? C1 N1 C6 C5 174.2(5) . . . . ? N2 C3 C7 C12 -170.2(4) . . . . ? N4 C3 C7 C12 10.5(6) . . . . ? N2 C3 C7 C8 14.2(7) . . . . ? N4 C3 C7 C8 -165.1(4) . . . . ? C12 C7 C8 C9 -0.8(7) . . . . ? C3 C7 C8 C9 174.8(5) . . . . ? C7 C8 C9 C10 -0.9(8) . . . . ? C8 C9 C10 C11 2.3(9) . . . . ? C9 C10 C11 C12 -1.9(9) . . . . ? C8 C7 C12 C11 1.2(8) . . . . ? C3 C7 C12 C11 -174.4(5) . . . . ? C10 C11 C12 C7 0.1(8) . . . . ? C25 P1 C13 C18 -123.6(5) . . . . ? C19 P1 C13 C18 126.0(5) . . . . ? Pt P1 C13 C18 5.6(5) . . . . ? C25 P1 C13 C14 60.9(5) . . . . ? C19 P1 C13 C14 -49.4(5) . . . . ? Pt P1 C13 C14 -169.9(4) . . . . ? C18 C13 C14 C15 5.3(8) . . . . ? P1 C13 C14 C15 -179.2(5) . . . . ? C13 C14 C15 C16 -1.9(10) . . . . ? C14 C15 C16 C17 -2.5(10) . . . . ? C15 C16 C17 C18 3.3(10) . . . . ? C14 C13 C18 C17 -4.7(9) . . . . ? P1 C13 C18 C17 179.7(5) . . . . ? C16 C17 C18 C13 0.3(10) . . . . ? C25 P1 C19 C20 7.8(5) . . . . ? C13 P1 C19 C20 120.2(4) . . . . ? Pt P1 C19 C20 -122.5(4) . . . . ? C25 P1 C19 C24 -172.3(4) . . . . ? C13 P1 C19 C24 -59.9(4) . . . . ? Pt P1 C19 C24 57.4(4) . . . . ? C24 C19 C20 C21 1.6(8) . . . . ? P1 C19 C20 C21 -178.5(4) . . . . ? C19 C20 C21 C22 -1.3(8) . . . . ? C20 C21 C22 C23 0.0(9) . . . . ? C21 C22 C23 C24 0.8(9) . . . . ? C22 C23 C24 C19 -0.5(9) . . . . ? C20 C19 C24 C23 -0.8(8) . . . . ? P1 C19 C24 C23 179.3(4) . . . . ? C19 P1 C25 C26 -104.3(4) . . . . ? C13 P1 C25 C26 149.8(4) . . . . ? Pt P1 C25 C26 24.5(5) . . . . ? C19 P1 C25 C30 73.6(5) . . . . ? C13 P1 C25 C30 -32.3(5) . . . . ? Pt P1 C25 C30 -157.6(4) . . . . ? C30 C25 C26 C27 1.3(8) . . . . ? P1 C25 C26 C27 179.3(4) . . . . ? C25 C26 C27 C28 -2.6(9) . . . . ? C26 C27 C28 C29 1.3(9) . . . . ? C27 C28 C29 C30 1.3(10) . . . . ? C28 C29 C30 C25 -2.6(10) . . . . ? C26 C25 C30 C29 1.3(9) . . . . ? P1 C25 C30 C29 -176.6(5) . . . . ? C37 P2 C31 C36 -56.0(5) . . . . ? C43 P2 C31 C36 -164.5(4) . . . . ? Pt P2 C31 C36 78.2(5) . . . . ? C37 P2 C31 C32 126.6(5) . . . . ? C43 P2 C31 C32 18.1(5) . . . . ? Pt P2 C31 C32 -99.2(5) . . . . ? C36 C31 C32 C33 0.2(9) . . . . ? P2 C31 C32 C33 177.6(5) . . . . ? C31 C32 C33 C34 0.9(11) . . . . ? C32 C33 C34 C35 -2.4(11) . . . . ? C33 C34 C35 C36 2.8(11) . . . . ? C32 C31 C36 C35 0.2(8) . . . . ? P2 C31 C36 C35 -177.3(5) . . . . ? C34 C35 C36 C31 -1.6(10) . . . . ? C31 P2 C37 C42 160.7(4) . . . . ? C43 P2 C37 C42 -89.1(4) . . . . ? Pt P2 C37 C42 24.8(5) . . . . ? C31 P2 C37 C38 -25.2(5) . . . . ? C43 P2 C37 C38 84.9(5) . . . . ? Pt P2 C37 C38 -161.2(4) . . . . ? C42 C37 C38 C39 -1.3(8) . . . . ? P2 C37 C38 C39 -175.5(5) . . . . ? C37 C38 C39 C40 2.9(10) . . . . ? C38 C39 C40 C41 -3.7(10) . . . . ? C39 C40 C41 C42 2.8(9) . . . . ? C40 C41 C42 C37 -1.2(8) . . . . ? C38 C37 C42 C41 0.4(8) . . . . ? P2 C37 C42 C41 174.5(4) . . . . ? C31 P2 C43 C48 -75.5(5) . . . . ? C37 P2 C43 C48 174.8(4) . . . . ? Pt P2 C43 C48 52.0(5) . . . . ? C31 P2 C43 C44 107.4(5) . . . . ? C37 P2 C43 C44 -2.3(5) . . . . ? Pt P2 C43 C44 -125.0(4) . . . . ? C48 C43 C44 C45 1.2(8) . . . . ? P2 C43 C44 C45 178.1(5) . . . . ? C43 C44 C45 C46 -0.1(10) . . . . ? C44 C45 C46 C47 -0.1(11) . . . . ? C45 C46 C47 C48 -0.8(11) . . . . ? C46 C47 C48 C43 1.8(10) . . . . ? C44 C43 C48 C47 -2.0(9) . . . . ? P2 C43 C48 C47 -179.1(5) . . . . ? C52 O1 C51 C53 -178.9(14) . . . . ? C51 O1 C52 C54 -177.1(12) . . . . ? _diffrn_measured_fraction_theta_max 0.964 _diffrn_reflns_theta_full 27.88 _diffrn_measured_fraction_theta_full 0.964 _refine_diff_density_max 0.996 _refine_diff_density_min -0.541 _refine_diff_density_rms 0.114 #===END data_3b _database_code_depnum_ccdc_archive 'CCDC 811784' #TrackingRef 'cif_data.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H13 N4 O 1+, N O3 1-' _chemical_formula_sum 'C12 H13 N5 O4' _chemical_formula_weight 291.27 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 monoclinic _symmetry_space_group_name_H-M 'P 21/n' 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 10.426(2) _cell_length_b 9.226(2) _cell_length_c 14.336(3) _cell_angle_alpha 90.00 _cell_angle_beta 94.01(2) _cell_angle_gamma 90.00 _cell_volume 1375.6(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.406 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.109 _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 293(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 'image plate dip1030' _diffrn_measurement_method 'laser scanner' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16205 _diffrn_reflns_av_R_equivalents 0.0391 _diffrn_reflns_av_sigmaI/netI 0.0305 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.63 _diffrn_reflns_theta_max 26.73 _reflns_number_total 2901 _reflns_number_gt 2134 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Nonius Xpress' _computing_cell_refinement 'Denzo (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELX97 (Sheldrick, 1998)' _computing_structure_refinement 'SHELX97 (Sheldrick, 1998)' _computing_molecular_graphics 'Ortep3/windows (Farrugia,1997)' _computing_publication_material 'Wingx 1.70.00 (Farrugia, 1999)' _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^ > 2\s(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^)+(0.1231P)^2^+0.1439P] 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_number_reflns 2901 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0764 _refine_ls_R_factor_gt 0.0621 _refine_ls_wR_factor_ref 0.2058 _refine_ls_wR_factor_gt 0.1920 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.085 _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 O2 O 1.19505(14) 0.23617(16) 0.46892(12) 0.0746(5) Uani 1 1 d . . . N1 N 1.09487(17) 0.04052(18) 0.40186(12) 0.0625(5) Uani 1 1 d . . . N3 N 0.98001(16) 0.25587(17) 0.43006(12) 0.0611(4) Uani 1 1 d . . . N4 N 0.76253(17) 0.27436(18) 0.38102(13) 0.0632(5) Uani 1 1 d . . . H4 H 0.706(2) 0.238(3) 0.3412(19) 0.076 Uiso 1 1 d . . . C1 C 1.2185(2) -0.0361(2) 0.40369(18) 0.0782(6) Uani 1 1 d . . . H1A H 1.2038 -0.1366 0.3893 0.117 Uiso 1 1 calc R . . H1B H 1.2619 -0.0275 0.4648 0.117 Uiso 1 1 calc R . . H1C H 1.2708 0.0058 0.3582 0.117 Uiso 1 1 calc R . . C2 C 1.09447(19) 0.1822(2) 0.43587(14) 0.0592(5) Uani 1 1 d . . . C4 C 0.87670(19) 0.1946(2) 0.39121(13) 0.0580(5) Uani 1 1 d . . . C5 C 0.8724(2) 0.0499(2) 0.35860(14) 0.0640(5) Uani 1 1 d . . . H5 H 0.7968 0.0072 0.3337 0.077 Uiso 1 1 calc R . . C6 C 0.9855(2) -0.0222(2) 0.36598(14) 0.0658(5) Uani 1 1 d . . . H6 H 0.9880 -0.1179 0.3457 0.079 Uiso 1 1 calc R . . N2 N 0.82962(19) 0.4821(2) 0.46070(15) 0.0711(5) Uani 1 1 d . . . H2A H 0.907(3) 0.444(3) 0.4696(18) 0.085 Uiso 1 1 d . . . H2B H 0.810(3) 0.571(3) 0.4831(18) 0.085 Uiso 1 1 d . . . C3 C 0.74139(19) 0.4110(2) 0.41237(14) 0.0590(5) Uani 1 1 d . . . C7 C 0.61412(19) 0.4755(2) 0.38871(13) 0.0590(5) Uani 1 1 d . . . C8 C 0.6037(2) 0.6237(2) 0.37113(15) 0.0656(5) Uani 1 1 d . . . H8 H 0.6769 0.6817 0.3760 0.079 Uiso 1 1 calc R . . C9 C 0.4854(2) 0.6850(3) 0.34655(17) 0.0754(6) Uani 1 1 d . . . H9 H 0.4789 0.7841 0.3353 0.090 Uiso 1 1 calc R . . C10 C 0.3766(2) 0.5987(3) 0.33867(17) 0.0781(6) Uani 1 1 d . . . H10 H 0.2971 0.6396 0.3208 0.094 Uiso 1 1 calc R . . C11 C 0.3857(2) 0.4528(3) 0.35713(17) 0.0762(6) Uani 1 1 d . . . H11 H 0.3120 0.3957 0.3524 0.091 Uiso 1 1 calc R . . C12 C 0.5031(2) 0.3903(2) 0.38265(14) 0.0657(5) Uani 1 1 d . . . H12 H 0.5083 0.2917 0.3958 0.079 Uiso 1 1 calc R . . N5 N 0.5237(2) 0.0984(2) 0.23481(18) 0.0834(6) Uani 1 1 d . . . O3 O 0.5297(4) 0.0364(3) 0.3126(3) 0.1773(15) Uani 1 1 d . . . O4 O 0.61351(18) 0.1811(2) 0.22490(13) 0.0907(6) Uani 1 1 d . . . O5 O 0.4374(2) 0.0894(5) 0.1765(3) 0.1905(19) 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 O2 0.0634(8) 0.0603(8) 0.0989(11) -0.0109(7) -0.0031(8) 0.0041(7) N1 0.0711(10) 0.0531(9) 0.0636(9) -0.0036(7) 0.0063(8) 0.0077(7) N3 0.0642(9) 0.0509(8) 0.0673(10) -0.0034(7) -0.0012(7) 0.0051(7) N4 0.0642(10) 0.0531(9) 0.0704(10) -0.0058(7) -0.0080(8) 0.0019(8) C1 0.0798(14) 0.0655(12) 0.0901(15) -0.0068(11) 0.0103(12) 0.0179(11) C2 0.0644(11) 0.0503(9) 0.0629(11) -0.0014(8) 0.0053(8) 0.0031(8) C4 0.0663(11) 0.0516(9) 0.0557(10) -0.0005(7) 0.0012(8) 0.0016(8) C5 0.0738(12) 0.0538(10) 0.0631(11) -0.0041(8) -0.0035(9) -0.0020(9) C6 0.0838(14) 0.0509(10) 0.0626(11) -0.0071(8) 0.0025(10) 0.0021(9) N2 0.0624(10) 0.0553(10) 0.0935(13) -0.0139(9) -0.0092(9) 0.0048(8) C3 0.0620(10) 0.0519(9) 0.0627(10) -0.0001(8) 0.0020(8) 0.0002(8) C7 0.0617(10) 0.0586(10) 0.0567(10) -0.0024(8) 0.0044(8) 0.0005(8) C8 0.0662(11) 0.0588(11) 0.0716(12) -0.0003(9) 0.0029(9) 0.0016(9) C9 0.0780(14) 0.0635(12) 0.0843(15) -0.0012(10) 0.0029(11) 0.0129(11) C10 0.0632(12) 0.0844(15) 0.0861(15) -0.0105(12) 0.0006(10) 0.0150(11) C11 0.0599(11) 0.0867(15) 0.0826(14) -0.0108(12) 0.0091(10) -0.0057(11) C12 0.0673(11) 0.0634(11) 0.0670(12) -0.0021(9) 0.0085(9) -0.0044(9) N5 0.0723(12) 0.0657(12) 0.1123(17) -0.0115(11) 0.0063(11) -0.0022(10) O3 0.233(4) 0.1034(19) 0.201(3) 0.034(2) 0.051(3) -0.028(2) O4 0.0852(11) 0.0927(13) 0.0936(12) -0.0044(9) 0.0022(9) -0.0032(10) O5 0.0788(15) 0.247(4) 0.238(4) -0.115(3) -0.0410(18) 0.0028(19) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O2 C2 1.226(2) . ? N1 C6 1.348(3) . ? N1 C2 1.395(2) . ? N1 C1 1.469(3) . ? N3 C4 1.306(3) . ? N3 C2 1.371(2) . ? N4 C3 1.361(3) . ? N4 C4 1.399(3) . ? N4 H4 0.86(3) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C4 C5 1.414(3) . ? C5 C6 1.352(3) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? N2 C3 1.291(3) . ? N2 H2A 0.88(3) . ? N2 H2B 0.91(3) . ? C3 C7 1.472(3) . ? C7 C8 1.394(3) . ? C7 C12 1.396(3) . ? C8 C9 1.380(3) . ? C8 H8 0.9300 . ? C9 C10 1.384(3) . ? C9 H9 0.9300 . ? C10 C11 1.374(4) . ? C10 H10 0.9300 . ? C11 C12 1.379(3) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? N5 O5 1.188(3) . ? N5 O4 1.224(3) . ? N5 O3 1.251(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 C6 N1 C2 120.83(17) . . ? C6 N1 C1 121.20(17) . . ? C2 N1 C1 117.94(17) . . ? C4 N3 C2 119.98(17) . . ? C3 N4 C4 127.54(17) . . ? C3 N4 H4 117.3(17) . . ? C4 N4 H4 113.9(16) . . ? N1 C1 H1A 109.5 . . ? N1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? N1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O2 C2 N3 122.68(18) . . ? O2 C2 N1 119.48(18) . . ? N3 C2 N1 117.84(17) . . ? N3 C4 N4 119.14(17) . . ? N3 C4 C5 123.76(19) . . ? N4 C4 C5 117.09(18) . . ? C6 C5 C4 115.57(19) . . ? C6 C5 H5 122.2 . . ? C4 C5 H5 122.2 . . ? N1 C6 C5 121.90(18) . . ? N1 C6 H6 119.0 . . ? C5 C6 H6 119.0 . . ? C3 N2 H2A 119.1(18) . . ? C3 N2 H2B 118.6(17) . . ? H2A N2 H2B 122(3) . . ? N2 C3 N4 121.46(19) . . ? N2 C3 C7 121.00(18) . . ? N4 C3 C7 117.54(17) . . ? C8 C7 C12 119.14(19) . . ? C8 C7 C3 119.73(18) . . ? C12 C7 C3 121.12(18) . . ? C9 C8 C7 120.3(2) . . ? C9 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? C8 C9 C10 119.9(2) . . ? C8 C9 H9 120.1 . . ? C10 C9 H9 120.1 . . ? C11 C10 C9 120.2(2) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C10 C11 C12 120.6(2) . . ? C10 C11 H11 119.7 . . ? C12 C11 H11 119.7 . . ? C11 C12 C7 119.8(2) . . ? C11 C12 H12 120.1 . . ? C7 C12 H12 120.1 . . ? O5 N5 O4 120.6(3) . . ? O5 N5 O3 125.7(4) . . ? O4 N5 O3 113.5(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 C4 N3 C2 O2 177.65(19) . . . . ? C4 N3 C2 N1 -1.9(3) . . . . ? C6 N1 C2 O2 179.33(19) . . . . ? C1 N1 C2 O2 -2.6(3) . . . . ? C6 N1 C2 N3 -1.1(3) . . . . ? C1 N1 C2 N3 177.00(18) . . . . ? C2 N3 C4 N4 -176.31(17) . . . . ? C2 N3 C4 C5 4.0(3) . . . . ? C3 N4 C4 N3 -4.3(3) . . . . ? C3 N4 C4 C5 175.36(19) . . . . ? N3 C4 C5 C6 -3.0(3) . . . . ? N4 C4 C5 C6 177.38(17) . . . . ? C2 N1 C6 C5 2.1(3) . . . . ? C1 N1 C6 C5 -175.91(19) . . . . ? C4 C5 C6 N1 -0.2(3) . . . . ? C4 N4 C3 N2 -2.8(3) . . . . ? C4 N4 C3 C7 176.86(18) . . . . ? N2 C3 C7 C8 34.5(3) . . . . ? N4 C3 C7 C8 -145.2(2) . . . . ? N2 C3 C7 C12 -146.1(2) . . . . ? N4 C3 C7 C12 34.2(3) . . . . ? C12 C7 C8 C9 -1.1(3) . . . . ? C3 C7 C8 C9 178.3(2) . . . . ? C7 C8 C9 C10 -0.4(4) . . . . ? C8 C9 C10 C11 1.3(4) . . . . ? C9 C10 C11 C12 -0.7(4) . . . . ? C10 C11 C12 C7 -0.8(3) . . . . ? C8 C7 C12 C11 1.7(3) . . . . ? C3 C7 C12 C11 -177.72(19) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 26.73 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.412 _refine_diff_density_min -0.261 _refine_diff_density_rms 0.046 #===END data_5b _database_code_depnum_ccdc_archive 'CCDC 811785' #TrackingRef 'cif_data.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H12 N4 O' _chemical_formula_weight 228.26 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 monoclinic _symmetry_space_group_name_H-M 'P 21/n' 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 7.374(2) _cell_length_b 11.022(3) _cell_length_c 13.990(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.40(2) _cell_angle_gamma 90.00 _cell_volume 1118.4(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.356 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 0.092 _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 293(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8953 _diffrn_reflns_av_R_equivalents 0.0590 _diffrn_reflns_av_sigmaI/netI 0.0767 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 25.02 _reflns_number_total 1874 _reflns_number_gt 795 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Nonius Xpress' _computing_cell_refinement 'Denzo (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELX97 (Sheldrick, 1998)' _computing_structure_refinement 'SHELX97 (Sheldrick, 1998)' _computing_molecular_graphics 'Ortep3/windows (Farrugia,1997)' _computing_publication_material 'Wingx 1.70.00 (Farrugia, 1999)' _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^ > 2\s(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^)+(0.0673P)^2^+0.0000P] 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_number_reflns 1874 _refine_ls_number_parameters 161 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1297 _refine_ls_R_factor_gt 0.0521 _refine_ls_wR_factor_ref 0.1492 _refine_ls_wR_factor_gt 0.1156 _refine_ls_goodness_of_fit_ref 0.866 _refine_ls_restrained_S_all 0.866 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.2571(3) 0.2795(2) 0.6803(2) 0.0668(8) Uani 1 1 d . . . N2 N 0.6842(4) 0.1009(3) 0.4816(3) 0.0812(10) Uani 1 1 d . . . H21 H 0.578(5) 0.086(3) 0.519(3) 0.097 Uiso 1 1 d . . . H22 H 0.715(5) 0.043(3) 0.440(3) 0.097 Uiso 1 1 d . . . N3 N 0.4696(3) 0.1817(2) 0.5988(2) 0.0662(8) Uani 1 1 d . . . N4 N 0.6929(3) 0.3011(2) 0.5397(2) 0.0671(8) Uani 1 1 d . . . O2 O 0.2470(3) 0.0775(2) 0.65773(19) 0.0869(8) Uani 1 1 d . . . C1 C 0.0958(4) 0.2704(3) 0.7276(3) 0.0801(11) Uani 1 1 d . . . H1A H 0.1168 0.2087 0.7769 0.120 Uiso 1 1 calc R . . H1B H -0.0107 0.2495 0.6802 0.120 Uiso 1 1 calc R . . H1C H 0.0755 0.3468 0.7568 0.120 Uiso 1 1 calc R . . C2 C 0.3247(5) 0.1750(3) 0.6462(2) 0.0667(9) Uani 1 1 d . . . C4 C 0.5455(4) 0.2885(3) 0.5863(2) 0.0627(9) Uani 1 1 d . . . C5 C 0.4761(5) 0.3954(3) 0.6201(3) 0.0757(10) Uani 1 1 d . . . H5 H 0.5267 0.4704 0.6092 0.091 Uiso 1 1 calc R . . C6 C 0.3358(5) 0.3876(3) 0.6684(3) 0.0766(10) Uani 1 1 d . . . H6 H 0.2920 0.4574 0.6940 0.092 Uiso 1 1 calc R . . C3 C 0.7548(4) 0.2117(3) 0.4921(3) 0.0635(9) Uani 1 1 d . . . C7 C 0.9153(4) 0.2402(3) 0.4458(2) 0.0619(9) Uani 1 1 d . . . C8 C 1.0219(5) 0.1507(3) 0.4148(3) 0.0778(10) Uani 1 1 d . . . H8 H 0.9943 0.0696 0.4237 0.093 Uiso 1 1 calc R . . C9 C 1.1688(5) 0.1801(4) 0.3709(3) 0.0846(12) Uani 1 1 d . . . H9 H 1.2400 0.1193 0.3502 0.102 Uiso 1 1 calc R . . C10 C 1.2092(5) 0.2990(4) 0.3580(3) 0.0873(12) Uani 1 1 d . . . H10 H 1.3079 0.3190 0.3280 0.105 Uiso 1 1 calc R . . C11 C 1.1061(5) 0.3889(4) 0.3886(3) 0.0918(12) Uani 1 1 d . . . H11 H 1.1345 0.4699 0.3796 0.110 Uiso 1 1 calc R . . C12 C 0.9604(5) 0.3593(3) 0.4327(3) 0.0765(10) Uani 1 1 d . . . H12 H 0.8910 0.4207 0.4540 0.092 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 N1 0.0680(16) 0.0667(18) 0.070(2) -0.0058(15) 0.0241(15) -0.0043(14) N2 0.094(2) 0.0551(18) 0.106(3) -0.0117(16) 0.0491(19) -0.0157(16) N3 0.0756(16) 0.0587(18) 0.0706(19) -0.0065(13) 0.0301(15) -0.0099(13) N4 0.0726(17) 0.0578(17) 0.076(2) -0.0075(14) 0.0274(15) -0.0082(13) O2 0.1065(17) 0.0688(15) 0.0979(19) -0.0124(14) 0.0520(15) -0.0234(14) C1 0.075(2) 0.092(3) 0.079(3) -0.008(2) 0.028(2) -0.0045(19) C2 0.076(2) 0.063(2) 0.066(2) -0.0064(17) 0.0250(19) -0.0085(18) C4 0.0646(19) 0.061(2) 0.066(2) -0.0057(17) 0.0201(17) -0.0084(17) C5 0.082(2) 0.056(2) 0.097(3) -0.0099(19) 0.036(2) -0.0055(17) C6 0.086(2) 0.062(2) 0.088(3) -0.0097(19) 0.031(2) 0.0003(19) C3 0.070(2) 0.058(2) 0.065(2) 0.0010(18) 0.0174(17) -0.0011(17) C7 0.0627(19) 0.059(2) 0.066(2) -0.0046(16) 0.0162(18) -0.0080(16) C8 0.077(2) 0.069(2) 0.092(3) -0.001(2) 0.026(2) -0.0027(19) C9 0.077(2) 0.082(3) 0.100(3) -0.010(2) 0.032(2) -0.004(2) C10 0.079(2) 0.097(3) 0.094(3) -0.006(2) 0.038(2) -0.015(2) C11 0.097(3) 0.075(2) 0.113(3) -0.006(2) 0.043(3) -0.019(2) C12 0.080(2) 0.070(2) 0.088(3) -0.004(2) 0.039(2) -0.0107(19) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C6 1.349(4) . ? N1 C2 1.374(4) . ? N1 C1 1.466(4) . ? N2 C3 1.325(4) . ? N3 C4 1.329(4) . ? N3 C2 1.358(4) . ? N4 C3 1.316(4) . ? N4 C4 1.372(4) . ? O2 C2 1.242(3) . ? C4 C5 1.401(4) . ? C5 C6 1.336(4) . ? C3 C7 1.482(4) . ? C7 C12 1.374(4) . ? C7 C8 1.379(4) . ? C8 C9 1.378(5) . ? C9 C10 1.363(5) . ? C10 C11 1.364(5) . ? C11 C12 1.371(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 C6 N1 C2 120.5(3) . . ? C6 N1 C1 121.2(3) . . ? C2 N1 C1 118.3(3) . . ? C4 N3 C2 120.0(3) . . ? C3 N4 C4 122.8(3) . . ? O2 C2 N3 122.2(3) . . ? O2 C2 N1 118.4(3) . . ? N3 C2 N1 119.4(3) . . ? N3 C4 N4 122.8(3) . . ? N3 C4 C5 120.8(3) . . ? N4 C4 C5 116.4(3) . . ? C6 C5 C4 118.7(3) . . ? C5 C6 N1 120.6(3) . . ? N4 C3 N2 125.5(3) . . ? N4 C3 C7 116.1(3) . . ? N2 C3 C7 118.4(3) . . ? C12 C7 C8 118.4(3) . . ? C12 C7 C3 119.5(3) . . ? C8 C7 C3 122.1(3) . . ? C9 C8 C7 120.7(3) . . ? C10 C9 C8 119.6(4) . . ? C9 C10 C11 120.6(3) . . ? C10 C11 C12 119.6(3) . . ? C11 C12 C7 121.1(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 C4 N3 C2 O2 178.5(3) . . . . ? C4 N3 C2 N1 0.5(5) . . . . ? C6 N1 C2 O2 -179.2(3) . . . . ? C1 N1 C2 O2 -0.5(5) . . . . ? C6 N1 C2 N3 -1.2(5) . . . . ? C1 N1 C2 N3 177.5(3) . . . . ? C2 N3 C4 N4 179.5(3) . . . . ? C2 N3 C4 C5 -1.1(5) . . . . ? C3 N4 C4 N3 9.5(5) . . . . ? C3 N4 C4 C5 -169.9(3) . . . . ? N3 C4 C5 C6 2.4(5) . . . . ? N4 C4 C5 C6 -178.2(3) . . . . ? C4 C5 C6 N1 -3.1(5) . . . . ? C2 N1 C6 C5 2.5(5) . . . . ? C1 N1 C6 C5 -176.1(3) . . . . ? C4 N4 C3 N2 1.1(5) . . . . ? C4 N4 C3 C7 -179.9(3) . . . . ? N4 C3 C7 C12 -16.5(5) . . . . ? N2 C3 C7 C12 162.6(3) . . . . ? N4 C3 C7 C8 163.7(3) . . . . ? N2 C3 C7 C8 -17.2(5) . . . . ? C12 C7 C8 C9 -0.6(5) . . . . ? C3 C7 C8 C9 179.1(4) . . . . ? C7 C8 C9 C10 0.0(6) . . . . ? C8 C9 C10 C11 0.3(6) . . . . ? C9 C10 C11 C12 -0.1(6) . . . . ? C10 C11 C12 C7 -0.6(6) . . . . ? C8 C7 C12 C11 0.9(5) . . . . ? C3 C7 C12 C11 -178.8(4) . . . . ? _diffrn_measured_fraction_theta_max 0.950 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.950 _refine_diff_density_max 0.207 _refine_diff_density_min -0.164 _refine_diff_density_rms 0.046 #===END data_6b _database_code_depnum_ccdc_archive 'CCDC 811786' #TrackingRef 'cif_data.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H12 N6' _chemical_formula_sum 'C13 H12 N6' _chemical_formula_weight 252.29 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.681(2) _cell_length_b 10.645(3) _cell_length_c 12.011(3) _cell_angle_alpha 110.88(2) _cell_angle_beta 91.87(2) _cell_angle_gamma 95.54(2) _cell_volume 1266.7(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.323 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.699 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enraf Nonius FR590' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kappa-CCD plate' _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_detector_area_resol_mean 14 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9412 _diffrn_reflns_av_R_equivalents 0.0515 _diffrn_reflns_av_sigmaI/netI 0.0679 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.95 _diffrn_reflns_theta_max 60.04 _reflns_number_total 3584 _reflns_number_gt 1458 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Supergui (Nonius BV, 1997-2000)' _computing_cell_refinement 'Denzo (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELX97 (Sheldrick, 1998)' _computing_structure_refinement 'SHELX97 (Sheldrick, 1998)' _computing_molecular_graphics 'Ortep3/windows (Farrugia,1997)' _computing_publication_material 'Wingx 1.70.00 (Farrugia, 1999)' _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^ > 2\s(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^)+(0.0936P)^2^+0.0000P] 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_number_reflns 3584 _refine_ls_number_parameters 357 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0796 _refine_ls_R_factor_gt 0.0507 _refine_ls_wR_factor_ref 0.1385 _refine_ls_wR_factor_gt 0.1238 _refine_ls_goodness_of_fit_ref 0.961 _refine_ls_restrained_S_all 0.961 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.5916(3) 0.6428(3) 0.2587(3) 0.0809(10) Uani 1 1 d . . . N2 N 0.8318(3) 0.6454(4) 0.2116(3) 0.0785(11) Uani 1 1 d . . . H2A H 0.761(4) 0.680(4) 0.225(4) 0.094 Uiso 1 1 d . . . H2B H 0.909(4) 0.688(4) 0.205(3) 0.094 Uiso 1 1 d . . . N3 N 0.3834(3) 0.6516(4) 0.3315(3) 0.0824(11) Uani 1 1 d . . . N6 N 0.7179(3) 0.4653(3) 0.2501(3) 0.0686(9) Uani 1 1 d . . . N7 N 0.4939(3) 0.3535(3) 0.3502(3) 0.0735(10) Uani 1 1 d . . . N9 N 0.3225(3) 0.4651(3) 0.3944(3) 0.0686(9) Uani 1 1 d . . . C2 C 0.4822(4) 0.6949(4) 0.2852(4) 0.0909(14) Uani 1 1 d . . . H2 H 0.4743 0.7729 0.2686 0.109 Uiso 1 1 calc R . . C3 C 0.8175(4) 0.5228(5) 0.2171(3) 0.0669(12) Uani 1 1 d . . . C4 C 0.4033(4) 0.5366(4) 0.3470(4) 0.0666(11) Uani 1 1 d . . . C5 C 0.5100(4) 0.4681(4) 0.3215(3) 0.0642(11) Uani 1 1 d . . . C6 C 0.6099(4) 0.5260(4) 0.2760(3) 0.0669(11) Uani 1 1 d . . . C8 C 0.3818(4) 0.3572(4) 0.3936(3) 0.0771(12) Uani 1 1 d . . . H8 H 0.3463 0.2916 0.4213 0.092 Uiso 1 1 calc R . . C9 C 0.1998(3) 0.5011(4) 0.4402(4) 0.0842(13) Uani 1 1 d . . . H9A H 0.1352 0.4289 0.3982 0.126 Uiso 1 1 calc R . . H9B H 0.1818 0.5823 0.4285 0.126 Uiso 1 1 calc R . . H9C H 0.2024 0.5158 0.5240 0.126 Uiso 1 1 calc R . . C10 C 0.9268(4) 0.4419(4) 0.1836(3) 0.0696(11) Uani 1 1 d . . . C11 C 0.9181(4) 0.3153(5) 0.1918(4) 0.0896(14) Uani 1 1 d . . . H11 H 0.8459 0.2839 0.2196 0.108 Uiso 1 1 calc R . . C12 C 1.0149(5) 0.2336(5) 0.1596(4) 0.1141(17) Uani 1 1 d . . . H12 H 1.0076 0.1485 0.1655 0.137 Uiso 1 1 calc R . . C13 C 1.1222(5) 0.2810(6) 0.1187(4) 0.1107(17) Uani 1 1 d . . . H13 H 1.1875 0.2272 0.0968 0.133 Uiso 1 1 calc R . . C14 C 1.1333(4) 0.4058(6) 0.1103(4) 0.1012(15) Uani 1 1 d . . . H14 H 1.2062 0.4369 0.0832 0.121 Uiso 1 1 calc R . . C15 C 1.0357(4) 0.4870(4) 0.1423(4) 0.0841(13) Uani 1 1 d . . . H15 H 1.0435 0.5719 0.1359 0.101 Uiso 1 1 calc R . . N21 N 0.9130(3) 0.1671(3) 0.4275(3) 0.0742(10) Uani 1 1 d . . . N22 N 0.6847(3) 0.1617(4) 0.3314(3) 0.0778(11) Uani 1 1 d . . . H22A H 0.756(4) 0.203(4) 0.389(3) 0.093 Uiso 1 1 d . . . H22B H 0.611(3) 0.210(4) 0.325(3) 0.093 Uiso 1 1 d . . . N23 N 1.1319(3) 0.1779(4) 0.4910(3) 0.0749(10) Uani 1 1 d . . . N26 N 0.8067(3) -0.0235(3) 0.2642(3) 0.0699(9) Uani 1 1 d . . . N27 N 1.0525(3) -0.1466(3) 0.2588(3) 0.0752(10) Uani 1 1 d . . . N29 N 1.2207(3) -0.0281(4) 0.3836(3) 0.0717(10) Uani 1 1 d . . . C22 C 1.0204(5) 0.2250(4) 0.4944(4) 0.0797(13) Uani 1 1 d . . . H22 H 1.0166 0.3104 0.5517 0.096 Uiso 1 1 calc R . . C23 C 0.7037(4) 0.0370(4) 0.2611(4) 0.0660(11) Uani 1 1 d . . . C24 C 1.1242(4) 0.0524(5) 0.4075(4) 0.0669(11) Uani 1 1 d . . . C25 C 1.0220(4) -0.0201(4) 0.3313(4) 0.0659(11) Uani 1 1 d . . . C26 C 0.9102(4) 0.0434(4) 0.3410(4) 0.0649(11) Uani 1 1 d . . . C28 C 1.1701(4) -0.1449(4) 0.2942(4) 0.0796(13) Uani 1 1 d . . . H28 H 1.2159 -0.2178 0.2610 0.096 Uiso 1 1 calc R . . C29 C 1.3441(3) 0.0035(4) 0.4505(4) 0.0865(13) Uani 1 1 d . . . H29A H 1.4066 0.0300 0.4049 0.130 Uiso 1 1 calc R . . H29B H 1.3660 -0.0750 0.4649 0.130 Uiso 1 1 calc R . . H29C H 1.3406 0.0763 0.5253 0.130 Uiso 1 1 calc R . . C30 C 0.5997(4) -0.0438(4) 0.1704(4) 0.0647(11) Uani 1 1 d . . . C31 C 0.6198(4) -0.1688(5) 0.0884(4) 0.0783(12) Uani 1 1 d . . . H31 H 0.6981 -0.1997 0.0893 0.094 Uiso 1 1 calc R . . C32 C 0.5252(5) -0.2476(5) 0.0057(4) 0.0993(15) Uani 1 1 d . . . H32 H 0.5403 -0.3311 -0.0488 0.119 Uiso 1 1 calc R . . C33 C 0.4074(5) -0.2037(5) 0.0029(4) 0.0996(15) Uani 1 1 d . . . H33 H 0.3434 -0.2580 -0.0526 0.120 Uiso 1 1 calc R . . C34 C 0.3859(4) -0.0796(5) 0.0825(4) 0.0908(14) Uani 1 1 d . . . H34 H 0.3073 -0.0493 0.0806 0.109 Uiso 1 1 calc R . . C35 C 0.4812(4) 0.0005(4) 0.1656(4) 0.0766(12) Uani 1 1 d . . . H35 H 0.4662 0.0848 0.2189 0.092 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 N1 0.063(2) 0.080(3) 0.109(3) 0.040(2) 0.0197(19) 0.024(2) N2 0.061(2) 0.075(3) 0.095(3) 0.025(2) 0.012(2) 0.013(2) N3 0.065(2) 0.078(3) 0.116(3) 0.044(2) 0.022(2) 0.023(2) N6 0.051(2) 0.072(2) 0.081(2) 0.0215(18) 0.0113(18) 0.015(2) N7 0.060(2) 0.073(3) 0.091(3) 0.030(2) 0.0157(18) 0.0189(18) N9 0.062(2) 0.067(2) 0.079(2) 0.0258(19) 0.0091(19) 0.018(2) C2 0.075(3) 0.089(3) 0.126(4) 0.054(3) 0.022(3) 0.031(3) C3 0.066(3) 0.062(3) 0.065(3) 0.011(2) 0.002(2) 0.016(3) C4 0.066(3) 0.062(3) 0.077(3) 0.029(2) 0.005(2) 0.013(3) C5 0.059(3) 0.058(3) 0.075(3) 0.020(2) 0.006(2) 0.018(2) C6 0.061(3) 0.065(3) 0.072(3) 0.021(2) 0.001(2) 0.016(3) C8 0.076(3) 0.063(3) 0.095(4) 0.031(2) 0.009(3) 0.014(3) C9 0.059(3) 0.097(3) 0.102(3) 0.036(3) 0.022(2) 0.029(2) C10 0.067(3) 0.074(3) 0.066(3) 0.020(2) 0.008(2) 0.018(3) C11 0.076(3) 0.107(4) 0.101(4) 0.047(3) 0.031(3) 0.038(3) C12 0.107(4) 0.128(4) 0.147(5) 0.081(4) 0.067(4) 0.060(4) C13 0.112(4) 0.122(5) 0.120(4) 0.054(4) 0.047(3) 0.067(4) C14 0.081(3) 0.118(4) 0.108(4) 0.036(3) 0.030(3) 0.035(3) C15 0.073(3) 0.090(3) 0.090(3) 0.032(3) 0.017(3) 0.014(3) N21 0.068(3) 0.064(2) 0.083(3) 0.017(2) 0.008(2) 0.0141(19) N22 0.064(2) 0.066(3) 0.096(3) 0.017(2) -0.001(2) 0.0218(19) N23 0.067(2) 0.079(3) 0.081(3) 0.029(2) 0.0081(19) 0.015(2) N26 0.057(2) 0.073(2) 0.080(3) 0.0248(19) 0.011(2) 0.021(2) N27 0.058(2) 0.070(2) 0.095(3) 0.023(2) 0.011(2) 0.0160(18) N29 0.055(2) 0.079(3) 0.085(3) 0.032(2) 0.007(2) 0.016(2) C22 0.073(3) 0.070(3) 0.088(3) 0.016(3) 0.011(3) 0.015(3) C23 0.064(3) 0.063(3) 0.073(3) 0.025(3) 0.015(3) 0.011(3) C24 0.060(3) 0.065(3) 0.077(3) 0.026(3) 0.012(3) 0.014(3) C25 0.062(3) 0.061(3) 0.073(3) 0.021(2) 0.012(3) 0.013(3) C26 0.061(3) 0.062(3) 0.076(3) 0.029(3) 0.010(3) 0.012(3) C28 0.063(3) 0.070(3) 0.101(4) 0.023(3) 0.009(3) 0.011(3) C29 0.065(3) 0.092(3) 0.105(3) 0.037(3) -0.004(3) 0.018(2) C30 0.067(3) 0.066(3) 0.061(3) 0.021(2) 0.010(2) 0.011(2) C31 0.076(3) 0.089(3) 0.069(3) 0.027(3) 0.002(3) 0.017(3) C32 0.100(4) 0.097(4) 0.088(4) 0.014(3) -0.004(3) 0.031(3) C33 0.099(4) 0.099(4) 0.087(4) 0.019(3) -0.018(3) 0.008(3) C34 0.070(3) 0.099(4) 0.100(4) 0.031(3) -0.002(3) 0.016(3) C35 0.063(3) 0.081(3) 0.084(3) 0.026(3) 0.005(3) 0.018(3) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C2 1.342(4) . ? N1 C6 1.361(4) . ? N2 C3 1.324(5) . ? N2 H2A 0.86(4) . ? N2 H2B 0.92(4) . ? N3 C2 1.327(5) . ? N3 C4 1.337(5) . ? N6 C3 1.319(5) . ? N6 C6 1.368(4) . ? N7 C8 1.320(4) . ? N7 C5 1.379(5) . ? N9 C8 1.361(4) . ? N9 C4 1.365(5) . ? N9 C9 1.470(4) . ? C2 H2 0.9300 . ? C3 C10 1.497(5) . ? C4 C5 1.396(5) . ? C5 C6 1.403(5) . ? C8 H8 0.9300 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.381(5) . ? C10 C15 1.389(5) . ? C11 C12 1.391(5) . ? C11 H11 0.9300 . ? C12 C13 1.382(6) . ? C12 H12 0.9300 . ? C13 C14 1.362(6) . ? C13 H13 0.9300 . ? C14 C15 1.395(5) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? N21 C22 1.338(5) . ? N21 C26 1.353(4) . ? N22 C23 1.334(5) . ? N22 H22A 0.96(4) . ? N22 H22B 0.99(4) . ? N23 C22 1.333(4) . ? N23 C24 1.347(5) . ? N26 C23 1.333(4) . ? N26 C26 1.376(5) . ? N27 C28 1.309(4) . ? N27 C25 1.395(4) . ? N29 C28 1.368(4) . ? N29 C24 1.376(4) . ? N29 C29 1.466(4) . ? C22 H22 0.9300 . ? C23 C30 1.493(5) . ? C24 C25 1.376(5) . ? C25 C26 1.417(5) . ? C28 H28 0.9300 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C30 C31 1.387(5) . ? C30 C35 1.400(5) . ? C31 C32 1.373(5) . ? C31 H31 0.9300 . ? C32 C33 1.387(5) . ? C32 H32 0.9300 . ? C33 C34 1.373(5) . ? C33 H33 0.9300 . ? C34 C35 1.385(5) . ? C34 H34 0.9300 . ? C35 H35 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 C2 N1 C6 119.4(4) . . ? C3 N2 H2A 109(3) . . ? C3 N2 H2B 123(3) . . ? H2A N2 H2B 128(4) . . ? C2 N3 C4 110.0(4) . . ? C3 N6 C6 122.0(4) . . ? C8 N7 C5 103.8(3) . . ? C8 N9 C4 105.3(3) . . ? C8 N9 C9 128.0(4) . . ? C4 N9 C9 126.7(3) . . ? N3 C2 N1 129.5(4) . . ? N3 C2 H2 115.3 . . ? N1 C2 H2 115.3 . . ? N6 C3 N2 126.8(4) . . ? N6 C3 C10 116.7(4) . . ? N2 C3 C10 116.5(5) . . ? N3 C4 N9 125.9(4) . . ? N3 C4 C5 127.5(5) . . ? N9 C4 C5 106.6(4) . . ? N7 C5 C4 109.8(4) . . ? N7 C5 C6 132.9(4) . . ? C4 C5 C6 117.3(4) . . ? N1 C6 N6 123.2(4) . . ? N1 C6 C5 116.3(4) . . ? N6 C6 C5 120.5(4) . . ? N7 C8 N9 114.4(4) . . ? N7 C8 H8 122.8 . . ? N9 C8 H8 122.8 . . ? N9 C9 H9A 109.5 . . ? N9 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N9 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 C15 118.2(4) . . ? C11 C10 C3 118.6(4) . . ? C15 C10 C3 123.1(5) . . ? C10 C11 C12 121.6(4) . . ? C10 C11 H11 119.2 . . ? C12 C11 H11 119.2 . . ? C13 C12 C11 118.9(5) . . ? C13 C12 H12 120.5 . . ? C11 C12 H12 120.5 . . ? C14 C13 C12 120.6(5) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C13 C14 C15 120.1(4) . . ? C13 C14 H14 119.9 . . ? C15 C14 H14 119.9 . . ? C10 C15 C14 120.5(4) . . ? C10 C15 H15 119.8 . . ? C14 C15 H15 119.8 . . ? C22 N21 C26 119.4(3) . . ? C23 N22 H22A 111(2) . . ? C23 N22 H22B 126(2) . . ? H22A N22 H22B 123(3) . . ? C22 N23 C24 109.6(3) . . ? C23 N26 C26 121.3(3) . . ? C28 N27 C25 103.2(3) . . ? C28 N29 C24 104.5(3) . . ? C28 N29 C29 129.4(4) . . ? C24 N29 C29 125.8(4) . . ? N23 C22 N21 129.4(4) . . ? N23 C22 H22 115.3 . . ? N21 C22 H22 115.3 . . ? N26 C23 N22 126.3(4) . . ? N26 C23 C30 116.4(4) . . ? N22 C23 C30 117.2(4) . . ? N23 C24 N29 125.1(4) . . ? N23 C24 C25 128.0(4) . . ? N29 C24 C25 106.9(4) . . ? C24 C25 N27 110.2(4) . . ? C24 C25 C26 116.8(4) . . ? N27 C25 C26 132.9(4) . . ? N21 C26 N26 124.4(3) . . ? N21 C26 C25 116.7(4) . . ? N26 C26 C25 118.9(4) . . ? N27 C28 N29 115.1(3) . . ? N27 C28 H28 122.5 . . ? N29 C28 H28 122.5 . . ? N29 C29 H29A 109.5 . . ? N29 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? N29 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C31 C30 C35 118.2(4) . . ? C31 C30 C23 119.1(4) . . ? C35 C30 C23 122.7(4) . . ? C32 C31 C30 120.8(4) . . ? C32 C31 H31 119.6 . . ? C30 C31 H31 119.6 . . ? C31 C32 C33 120.6(4) . . ? C31 C32 H32 119.7 . . ? C33 C32 H32 119.7 . . ? C34 C33 C32 119.6(4) . . ? C34 C33 H33 120.2 . . ? C32 C33 H33 120.2 . . ? C33 C34 C35 120.0(4) . . ? C33 C34 H34 120.0 . . ? C35 C34 H34 120.0 . . ? C34 C35 C30 120.8(4) . . ? C34 C35 H35 119.6 . . ? C30 C35 H35 119.6 . . ? 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 C4 N3 C2 N1 -2.5(6) . . . . ? C6 N1 C2 N3 2.3(6) . . . . ? C6 N6 C3 N2 4.7(6) . . . . ? C6 N6 C3 C10 -176.1(3) . . . . ? C2 N3 C4 N9 178.9(4) . . . . ? C2 N3 C4 C5 0.7(6) . . . . ? C8 N9 C4 N3 -179.5(4) . . . . ? C9 N9 C4 N3 -1.6(6) . . . . ? C8 N9 C4 C5 -1.0(4) . . . . ? C9 N9 C4 C5 177.0(3) . . . . ? C8 N7 C5 C4 -1.2(4) . . . . ? C8 N7 C5 C6 177.4(4) . . . . ? N3 C4 C5 N7 179.9(4) . . . . ? N9 C4 C5 N7 1.4(4) . . . . ? N3 C4 C5 C6 1.1(6) . . . . ? N9 C4 C5 C6 -177.4(3) . . . . ? C2 N1 C6 N6 179.2(3) . . . . ? C2 N1 C6 C5 -0.1(5) . . . . ? C3 N6 C6 N1 6.7(5) . . . . ? C3 N6 C6 C5 -174.0(3) . . . . ? N7 C5 C6 N1 -179.8(4) . . . . ? C4 C5 C6 N1 -1.3(5) . . . . ? N7 C5 C6 N6 0.8(6) . . . . ? C4 C5 C6 N6 179.3(3) . . . . ? C5 N7 C8 N9 0.6(4) . . . . ? C4 N9 C8 N7 0.3(4) . . . . ? C9 N9 C8 N7 -177.7(3) . . . . ? N6 C3 C10 C11 -1.5(5) . . . . ? N2 C3 C10 C11 177.8(4) . . . . ? N6 C3 C10 C15 177.2(3) . . . . ? N2 C3 C10 C15 -3.5(6) . . . . ? C15 C10 C11 C12 -0.2(6) . . . . ? C3 C10 C11 C12 178.6(4) . . . . ? C10 C11 C12 C13 0.2(7) . . . . ? C11 C12 C13 C14 0.1(7) . . . . ? C12 C13 C14 C15 -0.4(7) . . . . ? C11 C10 C15 C14 0.0(6) . . . . ? C3 C10 C15 C14 -178.8(4) . . . . ? C13 C14 C15 C10 0.4(7) . . . . ? C24 N23 C22 N21 -2.0(6) . . . . ? C26 N21 C22 N23 -0.7(6) . . . . ? C26 N26 C23 N22 -3.1(6) . . . . ? C26 N26 C23 C30 177.4(3) . . . . ? C22 N23 C24 N29 -177.3(3) . . . . ? C22 N23 C24 C25 2.3(6) . . . . ? C28 N29 C24 N23 179.5(4) . . . . ? C29 N29 C24 N23 5.3(6) . . . . ? C28 N29 C24 C25 -0.1(4) . . . . ? C29 N29 C24 C25 -174.4(3) . . . . ? N23 C24 C25 N27 -179.7(3) . . . . ? N29 C24 C25 N27 0.0(4) . . . . ? N23 C24 C25 C26 -0.2(6) . . . . ? N29 C24 C25 C26 179.4(3) . . . . ? C28 N27 C25 C24 0.2(4) . . . . ? C28 N27 C25 C26 -179.2(4) . . . . ? C22 N21 C26 N26 -177.6(3) . . . . ? C22 N21 C26 C25 3.0(5) . . . . ? C23 N26 C26 N21 7.7(6) . . . . ? C23 N26 C26 C25 -173.0(3) . . . . ? C24 C25 C26 N21 -2.6(5) . . . . ? N27 C25 C26 N21 176.7(4) . . . . ? C24 C25 C26 N26 178.0(3) . . . . ? N27 C25 C26 N26 -2.7(6) . . . . ? C25 N27 C28 N29 -0.3(5) . . . . ? C24 N29 C28 N27 0.3(5) . . . . ? C29 N29 C28 N27 174.3(3) . . . . ? N26 C23 C30 C31 -6.3(5) . . . . ? N22 C23 C30 C31 174.1(4) . . . . ? N26 C23 C30 C35 172.7(3) . . . . ? N22 C23 C30 C35 -6.9(5) . . . . ? C35 C30 C31 C32 -0.8(6) . . . . ? C23 C30 C31 C32 178.2(4) . . . . ? C30 C31 C32 C33 -0.2(7) . . . . ? C31 C32 C33 C34 0.9(7) . . . . ? C32 C33 C34 C35 -0.5(7) . . . . ? C33 C34 C35 C30 -0.5(6) . . . . ? C31 C30 C35 C34 1.1(6) . . . . ? C23 C30 C35 C34 -177.9(4) . . . . ? _diffrn_measured_fraction_theta_max 0.956 _diffrn_reflns_theta_full 60.04 _diffrn_measured_fraction_theta_full 0.956 _refine_diff_density_max 0.132 _refine_diff_density_min -0.167 _refine_diff_density_rms 0.034