# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Sylvia Draper' _publ_contact_author_email SMDRAPER@TCD.IE _publ_section_title ; N-substituted Pyridazines as Building Blocks in novel Supramolecular Architectures ; loop_ _publ_author_name 'Sylvia M. Draper' 'Gareth Cooke' 'Sunil Varughese' # Attachment '3_corrected.txt' data_3 _database_code_depnum_ccdc_archive 'CCDC 690255' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '1,3,5-Benzene-tri-2,6-2-pyridyl pyridazine' _chemical_melting_point ? _chemical_formula_moiety 'C48 H30 N12, C4 H10 O' _chemical_formula_sum 'C52 H40 N12 O' _chemical_formula_weight 848.96 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' Cl Cl 0.1484 0.1585 '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 12.676(1) _cell_length_b 13.597(1) _cell_length_c 13.826(1) _cell_angle_alpha 73.300(2) _cell_angle_beta 76.270(2) _cell_angle_gamma 78.950(2) _cell_volume 2197.7(3) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 7172 _cell_measurement_theta_min 4.363 _cell_measurement_theta_max 49.789 _exptl_crystal_description Blocks _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.283 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 888 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type 'multi scan' _exptl_absorpt_correction_T_min 0.9840 _exptl_absorpt_correction_T_max 0.9919 _exptl_absorpt_process_details 'SADABS; Sheldrick, 1997' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(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 'CCD Area Detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23851 _diffrn_reflns_av_R_equivalents 0.0273 _diffrn_reflns_av_sigmaI/netI 0.0294 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 25.15 _reflns_number_total 7857 _reflns_number_gt 6143 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement SAINTPLUS _computing_data_reduction SAINTPLUS _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1277P)^2^+0.6520P] 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 7857 _refine_ls_number_parameters 586 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0782 _refine_ls_R_factor_gt 0.0640 _refine_ls_wR_factor_ref 0.2066 _refine_ls_wR_factor_gt 0.1902 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _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 0.83494(16) 0.51038(16) 0.30848(15) 0.0394(4) Uani 1 1 d . . . C2 C 0.80637(17) 0.61710(16) 0.28046(15) 0.0419(5) Uani 1 1 d . . . H2 H 0.8455 0.6564 0.2209 0.050 Uiso 1 1 calc R . . C3 C 0.72058(16) 0.66549(15) 0.34004(15) 0.0392(4) Uani 1 1 d . . . C4 C 0.66214(16) 0.60528(15) 0.42823(15) 0.0384(4) Uani 1 1 d . . . H4 H 0.6031 0.6373 0.4677 0.046 Uiso 1 1 calc R . . C5 C 0.68967(15) 0.49878(15) 0.45873(14) 0.0369(4) Uani 1 1 d . . . C6 C 0.77725(15) 0.45183(15) 0.39753(14) 0.0377(4) Uani 1 1 d . . . H6 H 0.7970 0.3805 0.4168 0.045 Uiso 1 1 calc R . . C13 C 1.03098(18) 0.48383(18) 0.20835(17) 0.0494(5) Uani 1 1 d . . . C14 C 0.92277(17) 0.45941(16) 0.23931(15) 0.0426(5) Uani 1 1 d . . . C15 C 0.89949(18) 0.38849(17) 0.19691(17) 0.0487(5) Uani 1 1 d . . . H15 H 0.8301 0.3678 0.2152 0.058 Uiso 1 1 calc R . . C16 C 0.98089(19) 0.34760(18) 0.12607(18) 0.0527(6) Uani 1 1 d . . . C17 C 1.07176(17) 0.55293(18) 0.25304(17) 0.0490(5) Uani 1 1 d . . . C19 C 1.0733(2) 0.6017(2) 0.3971(2) 0.0714(8) Uani 1 1 d . . . H19 H 1.0510 0.5938 0.4677 0.086 Uiso 1 1 calc R . . C33 C 0.65982(19) 0.84604(17) 0.37338(18) 0.0503(5) Uani 1 1 d . . . C34 C 0.68870(17) 0.77929(16) 0.30667(16) 0.0435(5) Uani 1 1 d . . . C35 C 0.68255(18) 0.82545(17) 0.20547(17) 0.0490(5) Uani 1 1 d . . . H35 H 0.7020 0.7864 0.1572 0.059 Uiso 1 1 calc R . . C36 C 0.64703(19) 0.93104(18) 0.17572(19) 0.0543(6) Uani 1 1 d . . . C37 C 0.6722(2) 0.81412(17) 0.48281(19) 0.0543(6) Uani 1 1 d . . . C39 C 0.7696(3) 0.7142(3) 0.6032(3) 0.0884(10) Uani 1 1 d . . . H39 H 0.8277 0.6638 0.6204 0.106 Uiso 1 1 calc R . . C53 C 0.60832(16) 0.33652(15) 0.58071(16) 0.0424(5) Uani 1 1 d . . . C54 C 0.62777(16) 0.44061(15) 0.55785(15) 0.0393(4) Uani 1 1 d . . . C55 C 0.58827(17) 0.48827(17) 0.63705(15) 0.0448(5) Uani 1 1 d . . . H55 H 0.6002 0.5559 0.6284 0.054 Uiso 1 1 calc R . . C56 C 0.53047(17) 0.43512(18) 0.73017(16) 0.0475(5) Uani 1 1 d . . . C57 C 0.63809(17) 0.27137(16) 0.50583(17) 0.0460(5) Uani 1 1 d . . . C59 C 0.6420(2) 0.2583(2) 0.3444(2) 0.0683(7) Uani 1 1 d . . . H59 H 0.6260 0.2884 0.2792 0.082 Uiso 1 1 calc R . . C72 C 1.0374(13) -0.0395(5) 0.2837(8) 0.320(9) Uani 1 1 d . . . H72A H 1.0870 -0.0887 0.3237 0.384 Uiso 1 1 calc R . . H72B H 1.0743 -0.0165 0.2127 0.384 Uiso 1 1 calc R . . C73 C 0.9334(5) -0.0787(5) 0.2933(5) 0.1403(18) Uani 1 1 d . . . H73A H 0.8991 -0.0981 0.3646 0.210 Uiso 1 1 calc R . . H73B H 0.9482 -0.1381 0.2654 0.210 Uiso 1 1 calc R . . H73C H 0.8855 -0.0256 0.2562 0.210 Uiso 1 1 calc R . . C74 C 1.0734(10) 0.0740(10) 0.3399(6) 0.228(5) Uani 1 1 d . . . H74A H 1.1176 0.1053 0.2745 0.274 Uiso 1 1 calc R . . H74B H 1.1180 0.0180 0.3794 0.274 Uiso 1 1 calc R . . C75 C 1.0136(9) 0.1548(11) 0.4008(9) 0.323(9) Uani 1 1 d . . . H75A H 0.9683 0.2071 0.3600 0.485 Uiso 1 1 calc R . . H75B H 1.0667 0.1863 0.4169 0.485 Uiso 1 1 calc R . . H75C H 0.9688 0.1210 0.4635 0.485 Uiso 1 1 calc R . . C110 C 1.1389(2) 0.6761(2) 0.3425(3) 0.0738(8) Uani 1 1 d . . . H110 H 1.1595 0.7183 0.3752 0.089 Uiso 1 1 calc R . . C111 C 1.1734(2) 0.6872(2) 0.2394(3) 0.0765(8) Uani 1 1 d . . . H111 H 1.2193 0.7363 0.2007 0.092 Uiso 1 1 calc R . . C112 C 1.1395(2) 0.6248(2) 0.1930(2) 0.0669(7) Uani 1 1 d . . . H112 H 1.1619 0.6311 0.1226 0.080 Uiso 1 1 calc R . . C113 C 0.9604(2) 0.26991(19) 0.07867(19) 0.0564(6) Uani 1 1 d . . . C115 C 0.8373(3) 0.1758(2) 0.0639(3) 0.0827(9) Uani 1 1 d . . . H115 H 0.7667 0.1579 0.0818 0.099 Uiso 1 1 calc R . . C116 C 0.9134(3) 0.1289(2) -0.0034(3) 0.0875(10) Uani 1 1 d . . . H116 H 0.8945 0.0817 -0.0314 0.105 Uiso 1 1 calc R . . C117 C 1.0178(3) 0.1534(3) -0.0282(3) 0.0899(10) Uani 1 1 d . . . H117 H 1.0716 0.1219 -0.0726 0.108 Uiso 1 1 calc R . . C118 C 1.0425(3) 0.2246(2) 0.0127(2) 0.0739(8) Uani 1 1 d . . . H118 H 1.1130 0.2423 -0.0035 0.089 Uiso 1 1 calc R . . C310 C 0.6999(4) 0.7528(3) 0.6806(3) 0.0929(10) Uani 1 1 d . . . H310 H 0.7114 0.7299 0.7479 0.111 Uiso 1 1 calc R . . C311 C 0.6144(3) 0.8246(3) 0.6563(2) 0.0892(10) Uani 1 1 d . . . H311 H 0.5663 0.8524 0.7069 0.107 Uiso 1 1 calc R . . C312 C 0.5990(3) 0.8564(2) 0.5562(2) 0.0698(7) Uani 1 1 d . . . H312 H 0.5402 0.9056 0.5383 0.084 Uiso 1 1 calc R . . C313 C 0.6421(2) 0.9848(2) 0.0667(2) 0.0613(7) Uani 1 1 d . . . C315 C 0.6937(3) 0.9798(3) -0.1008(3) 0.1056(12) Uani 1 1 d . . . H315 H 0.7326 0.9452 -0.1502 0.127 Uiso 1 1 calc R . . C316 C 0.6364(3) 1.0758(4) -0.1335(3) 0.1059(13) Uani 1 1 d . . . H316 H 0.6358 1.1048 -0.2031 0.127 Uiso 1 1 calc R . . C317 C 0.5809(3) 1.1270(3) -0.0624(3) 0.0963(12) Uani 1 1 d . . . H317 H 0.5414 1.1921 -0.0824 0.116 Uiso 1 1 calc R . . C318 C 0.5833(3) 1.0822(2) 0.0388(3) 0.0778(9) Uani 1 1 d . . . H318 H 0.5460 1.1166 0.0888 0.093 Uiso 1 1 calc R . . C510 C 0.6926(3) 0.1598(2) 0.3634(3) 0.0768(8) Uani 1 1 d . . . H510 H 0.7118 0.1240 0.3123 0.092 Uiso 1 1 calc R . . C511 C 0.7147(3) 0.1139(2) 0.4592(3) 0.0826(9) Uani 1 1 d . . . H511 H 0.7476 0.0455 0.4750 0.099 Uiso 1 1 calc R . . C512 C 0.6876(2) 0.17056(19) 0.5332(2) 0.0677(7) Uani 1 1 d . . . H512 H 0.7023 0.1413 0.5990 0.081 Uiso 1 1 calc R . . C513 C 0.4788(2) 0.4871(2) 0.81394(16) 0.0552(6) Uani 1 1 d . . . C515 C 0.4787(3) 0.6168(3) 0.8885(2) 0.0809(9) Uani 1 1 d . . . H515 H 0.5108 0.6721 0.8904 0.097 Uiso 1 1 calc R . . C516 C 0.3875(3) 0.5923(3) 0.9596(2) 0.0853(10) Uani 1 1 d . . . H516 H 0.3586 0.6292 1.0092 0.102 Uiso 1 1 calc R . . C517 C 0.3393(3) 0.5124(3) 0.9568(2) 0.0904(11) Uani 1 1 d . . . H517 H 0.2757 0.4948 1.0037 0.108 Uiso 1 1 calc R . . C518 C 0.3858(2) 0.4569(3) 0.8830(2) 0.0756(8) Uani 1 1 d . . . H518 H 0.3550 0.4011 0.8805 0.091 Uiso 1 1 calc R . . N11 N 1.07988(18) 0.37771(19) 0.09544(18) 0.0704(6) Uani 1 1 d . . . N12 N 1.10488(17) 0.44515(19) 0.13795(18) 0.0680(6) Uani 1 1 d . . . N18 N 1.03970(17) 0.53978(17) 0.35429(16) 0.0602(5) Uani 1 1 d . . . N31 N 0.6142(2) 0.98875(16) 0.24327(19) 0.0697(6) Uani 1 1 d . . . N32 N 0.6220(2) 0.94608(15) 0.34150(18) 0.0679(6) Uani 1 1 d . . . N38 N 0.7584(2) 0.74505(18) 0.50476(18) 0.0709(6) Uani 1 1 d . . . N51 N 0.51884(16) 0.33605(16) 0.74865(14) 0.0555(5) Uani 1 1 d . . . N52 N 0.55912(16) 0.28662(14) 0.67398(14) 0.0521(5) Uani 1 1 d . . . N58 N 0.61359(17) 0.31543(15) 0.41273(16) 0.0554(5) Uani 1 1 d . . . N114 N 0.8584(2) 0.24537(18) 0.10523(19) 0.0709(6) Uani 1 1 d . . . N314 N 0.6967(2) 0.9332(2) -0.00174(18) 0.0815(7) Uani 1 1 d . . . N514 N 0.5256(2) 0.56633(18) 0.81534(16) 0.0682(6) Uani 1 1 d . . . O71 O 0.9862(4) 0.0445(6) 0.3285(5) 0.228(3) 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 0.0362(10) 0.0420(11) 0.0374(10) -0.0104(8) -0.0020(8) -0.0047(8) C2 0.0414(11) 0.0419(11) 0.0363(10) -0.0035(8) -0.0015(8) -0.0082(9) C3 0.0389(10) 0.0369(10) 0.0396(10) -0.0079(8) -0.0064(8) -0.0040(8) C4 0.0355(10) 0.0382(10) 0.0372(10) -0.0093(8) -0.0026(8) -0.0003(8) C5 0.0353(10) 0.0378(10) 0.0340(10) -0.0057(8) -0.0050(8) -0.0035(8) C6 0.0368(10) 0.0345(10) 0.0387(10) -0.0086(8) -0.0044(8) -0.0019(8) C13 0.0443(12) 0.0522(13) 0.0458(12) -0.0130(10) 0.0031(9) -0.0063(10) C14 0.0414(11) 0.0426(11) 0.0366(10) -0.0069(9) 0.0001(8) -0.0027(9) C15 0.0449(12) 0.0504(12) 0.0473(12) -0.0151(10) 0.0019(9) -0.0073(10) C16 0.0510(13) 0.0542(13) 0.0491(13) -0.0172(10) 0.0001(10) -0.0039(10) C17 0.0376(11) 0.0524(13) 0.0529(13) -0.0139(10) -0.0026(9) -0.0031(9) C19 0.0707(17) 0.092(2) 0.0616(16) -0.0228(15) -0.0213(14) -0.0185(15) C33 0.0514(13) 0.0381(11) 0.0594(14) -0.0104(10) -0.0085(10) -0.0074(9) C34 0.0407(11) 0.0367(10) 0.0483(12) -0.0041(9) -0.0050(9) -0.0081(8) C35 0.0493(12) 0.0411(11) 0.0508(12) -0.0039(10) -0.0059(10) -0.0089(9) C36 0.0513(13) 0.0422(12) 0.0621(14) 0.0032(11) -0.0131(11) -0.0112(10) C37 0.0639(15) 0.0412(12) 0.0588(14) -0.0108(10) -0.0122(11) -0.0119(11) C39 0.106(3) 0.088(2) 0.081(2) -0.0207(18) -0.045(2) -0.0032(19) C53 0.0354(10) 0.0396(11) 0.0429(11) -0.0005(9) -0.0046(8) -0.0020(8) C54 0.0349(10) 0.0392(10) 0.0368(10) -0.0028(8) -0.0049(8) -0.0010(8) C55 0.0463(12) 0.0425(11) 0.0374(11) -0.0059(9) -0.0020(9) -0.0006(9) C56 0.0415(11) 0.0526(13) 0.0374(11) -0.0016(9) -0.0039(9) 0.0003(9) C57 0.0406(11) 0.0379(11) 0.0538(13) -0.0064(9) -0.0015(9) -0.0089(9) C59 0.0753(18) 0.0715(18) 0.0677(17) -0.0255(14) -0.0174(14) -0.0160(14) C72 0.53(2) 0.096(5) 0.271(11) -0.074(6) 0.117(13) -0.089(8) C73 0.141(4) 0.122(4) 0.156(5) -0.057(4) -0.006(4) -0.005(3) C74 0.237(11) 0.346(15) 0.131(6) -0.070(7) -0.014(6) -0.123(10) C75 0.270(12) 0.408(18) 0.287(13) 0.132(12) -0.157(11) -0.244(14) C110 0.0709(18) 0.0752(18) 0.089(2) -0.0257(16) -0.0339(16) -0.0120(15) C111 0.0705(18) 0.0692(18) 0.092(2) -0.0136(16) -0.0138(16) -0.0281(15) C112 0.0624(16) 0.0704(17) 0.0646(16) -0.0164(13) 0.0026(13) -0.0209(13) C113 0.0623(15) 0.0524(13) 0.0521(13) -0.0182(11) -0.0046(11) -0.0019(11) C115 0.088(2) 0.0725(19) 0.098(2) -0.0357(17) -0.0183(18) -0.0148(16) C116 0.120(3) 0.0655(18) 0.090(2) -0.0387(17) -0.025(2) -0.0081(18) C117 0.106(3) 0.081(2) 0.089(2) -0.0511(18) -0.0034(19) -0.0017(19) C118 0.0797(19) 0.0707(17) 0.0713(17) -0.0360(15) 0.0031(14) -0.0042(14) C310 0.119(3) 0.103(3) 0.0620(19) -0.0155(18) -0.0261(19) -0.025(2) C311 0.104(3) 0.100(3) 0.0617(18) -0.0241(17) 0.0007(17) -0.026(2) C312 0.0743(18) 0.0609(16) 0.0668(17) -0.0155(13) -0.0008(13) -0.0085(13) C313 0.0538(14) 0.0551(14) 0.0641(16) 0.0109(12) -0.0141(12) -0.0181(11) C315 0.097(3) 0.130(3) 0.0606(19) 0.014(2) -0.0046(17) -0.018(2) C316 0.099(3) 0.118(3) 0.074(2) 0.044(2) -0.032(2) -0.038(2) C317 0.092(2) 0.073(2) 0.105(3) 0.037(2) -0.045(2) -0.0289(18) C318 0.0817(19) 0.0502(14) 0.093(2) 0.0174(14) -0.0376(16) -0.0161(14) C510 0.092(2) 0.0650(18) 0.081(2) -0.0351(16) -0.0040(16) -0.0190(16) C511 0.097(2) 0.0405(14) 0.101(2) -0.0223(15) -0.0022(18) -0.0011(14) C512 0.0798(18) 0.0426(13) 0.0672(16) -0.0046(12) -0.0064(14) 0.0002(12) C513 0.0537(13) 0.0649(15) 0.0348(11) -0.0052(10) -0.0051(10) 0.0054(11) C515 0.104(2) 0.0781(19) 0.0526(16) -0.0226(14) -0.0062(15) 0.0049(17) C516 0.079(2) 0.108(3) 0.0553(17) -0.0301(17) -0.0036(15) 0.0205(19) C517 0.0614(18) 0.137(3) 0.0571(17) -0.0300(19) 0.0137(14) 0.000(2) C518 0.0553(15) 0.109(2) 0.0524(15) -0.0209(15) 0.0080(12) -0.0097(15) N11 0.0577(13) 0.0829(16) 0.0733(14) -0.0421(13) 0.0149(11) -0.0160(11) N12 0.0495(12) 0.0837(15) 0.0720(14) -0.0399(12) 0.0163(10) -0.0160(11) N18 0.0574(12) 0.0730(14) 0.0521(12) -0.0151(10) -0.0094(9) -0.0153(10) N31 0.0896(16) 0.0382(11) 0.0750(15) -0.0029(10) -0.0225(12) -0.0026(10) N32 0.0911(16) 0.0383(10) 0.0715(14) -0.0103(10) -0.0193(12) -0.0030(10) N38 0.0807(16) 0.0678(14) 0.0719(15) -0.0238(12) -0.0312(12) 0.0018(12) N51 0.0542(11) 0.0572(12) 0.0410(10) 0.0003(9) 0.0006(8) -0.0055(9) N52 0.0504(11) 0.0467(10) 0.0471(10) 0.0006(8) -0.0015(8) -0.0066(8) N58 0.0581(12) 0.0533(11) 0.0573(12) -0.0151(9) -0.0150(9) -0.0070(9) N114 0.0711(15) 0.0681(14) 0.0806(15) -0.0342(12) -0.0078(12) -0.0108(11) N314 0.0742(16) 0.0908(18) 0.0554(13) 0.0116(13) -0.0067(12) -0.0071(13) N514 0.0825(15) 0.0681(14) 0.0440(11) -0.0150(10) 0.0022(10) -0.0032(12) O71 0.139(4) 0.254(7) 0.299(8) -0.075(6) -0.067(4) -0.008(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 C6 1.385(3) . ? C1 C2 1.389(3) . ? C1 C14 1.488(3) . ? C2 C3 1.381(3) . ? C3 C4 1.391(3) . ? C3 C34 1.486(3) . ? C4 C5 1.386(3) . ? C5 C6 1.396(3) . ? C5 C54 1.491(3) . ? C13 N12 1.332(3) . ? C13 C14 1.410(3) . ? C13 C17 1.484(3) . ? C14 C15 1.370(3) . ? C15 C16 1.395(3) . ? C16 N11 1.329(3) . ? C16 C113 1.482(3) . ? C17 N18 1.331(3) . ? C17 C112 1.378(3) . ? C19 N18 1.336(3) . ? C19 C110 1.368(4) . ? C33 N32 1.334(3) . ? C33 C34 1.415(3) . ? C33 C37 1.487(3) . ? C34 C35 1.373(3) . ? C35 C36 1.391(3) . ? C36 N31 1.331(3) . ? C36 C313 1.484(3) . ? C37 N38 1.330(3) . ? C37 C312 1.380(4) . ? C39 N38 1.338(4) . ? C39 C310 1.377(5) . ? C53 N52 1.338(3) . ? C53 C54 1.415(3) . ? C53 C57 1.488(3) . ? C54 C55 1.376(3) . ? C55 C56 1.392(3) . ? C56 N51 1.327(3) . ? C56 C513 1.484(3) . ? C57 N58 1.337(3) . ? C57 C512 1.378(3) . ? C59 N58 1.334(3) . ? C59 C510 1.350(4) . ? C72 O71 1.428(9) . ? C72 C73 1.478(14) . ? C74 O71 1.303(10) . ? C74 C75 1.549(17) . ? C110 C111 1.361(4) . ? C111 C112 1.378(4) . ? C113 N114 1.338(4) . ? C113 C118 1.386(4) . ? C115 N114 1.331(4) . ? C115 C116 1.373(5) . ? C116 C117 1.367(5) . ? C117 C118 1.368(4) . ? C310 C311 1.348(5) . ? C311 C312 1.376(4) . ? C313 N314 1.323(4) . ? C313 C318 1.386(4) . ? C315 N314 1.340(4) . ? C315 C316 1.375(6) . ? C316 C317 1.350(6) . ? C317 C318 1.362(5) . ? C510 C511 1.362(5) . ? C511 C512 1.394(4) . ? C513 N514 1.332(4) . ? C513 C518 1.377(4) . ? C515 N514 1.344(3) . ? C515 C516 1.354(5) . ? C516 C517 1.358(5) . ? C517 C518 1.394(4) . ? N11 N12 1.340(3) . ? N31 N32 1.334(3) . ? N51 N52 1.340(3) . ? 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 C1 C2 119.67(18) . . ? C6 C1 C14 120.57(18) . . ? C2 C1 C14 119.66(17) . . ? C3 C2 C1 120.77(18) . . ? C2 C3 C4 118.81(18) . . ? C2 C3 C34 119.91(18) . . ? C4 C3 C34 121.21(17) . . ? C5 C4 C3 121.66(17) . . ? C4 C5 C6 118.39(17) . . ? C4 C5 C54 118.39(17) . . ? C6 C5 C54 123.15(17) . . ? C1 C6 C5 120.69(18) . . ? N12 C13 C14 122.5(2) . . ? N12 C13 C17 114.9(2) . . ? C14 C13 C17 122.62(19) . . ? C15 C14 C13 115.92(19) . . ? C15 C14 C1 120.28(19) . . ? C13 C14 C1 123.71(19) . . ? C14 C15 C16 119.3(2) . . ? N11 C16 C15 122.1(2) . . ? N11 C16 C113 116.3(2) . . ? C15 C16 C113 121.5(2) . . ? N18 C17 C112 122.7(2) . . ? N18 C17 C13 115.6(2) . . ? C112 C17 C13 121.7(2) . . ? N18 C19 C110 123.4(3) . . ? N32 C33 C34 122.1(2) . . ? N32 C33 C37 113.6(2) . . ? C34 C33 C37 124.26(19) . . ? C35 C34 C33 115.74(19) . . ? C35 C34 C3 119.79(19) . . ? C33 C34 C3 124.44(19) . . ? C34 C35 C36 119.6(2) . . ? N31 C36 C35 122.0(2) . . ? N31 C36 C313 116.6(2) . . ? C35 C36 C313 121.4(2) . . ? N38 C37 C312 122.5(2) . . ? N38 C37 C33 116.3(2) . . ? C312 C37 C33 121.2(2) . . ? N38 C39 C310 123.7(3) . . ? N52 C53 C54 122.4(2) . . ? N52 C53 C57 112.77(18) . . ? C54 C53 C57 124.83(18) . . ? C55 C54 C53 115.25(18) . . ? C55 C54 C5 119.14(18) . . ? C53 C54 C5 125.57(18) . . ? C54 C55 C56 119.9(2) . . ? N51 C56 C55 122.0(2) . . ? N51 C56 C513 116.78(19) . . ? C55 C56 C513 121.2(2) . . ? N58 C57 C512 122.7(2) . . ? N58 C57 C53 116.62(18) . . ? C512 C57 C53 120.6(2) . . ? N58 C59 C510 124.5(3) . . ? O71 C72 C73 94.3(9) . . ? O71 C74 C75 97.1(9) . . ? C111 C110 C19 118.7(3) . . ? C110 C111 C112 119.2(3) . . ? C17 C112 C111 118.6(3) . . ? N114 C113 C118 122.5(2) . . ? N114 C113 C16 115.6(2) . . ? C118 C113 C16 121.9(2) . . ? N114 C115 C116 124.0(3) . . ? C117 C116 C115 118.2(3) . . ? C116 C117 C118 119.5(3) . . ? C117 C118 C113 118.8(3) . . ? C311 C310 C39 118.3(3) . . ? C310 C311 C312 119.5(3) . . ? C311 C312 C37 118.9(3) . . ? N314 C313 C318 122.3(3) . . ? N314 C313 C36 115.6(2) . . ? C318 C313 C36 122.1(3) . . ? N314 C315 C316 123.6(4) . . ? C317 C316 C315 118.6(3) . . ? C316 C317 C318 119.2(3) . . ? C317 C318 C313 119.4(4) . . ? C59 C510 C511 118.5(3) . . ? C510 C511 C512 119.4(3) . . ? C57 C512 C511 117.9(3) . . ? N514 C513 C518 122.7(2) . . ? N514 C513 C56 115.9(2) . . ? C518 C513 C56 121.4(3) . . ? N514 C515 C516 124.0(4) . . ? C515 C516 C517 118.4(3) . . ? C516 C517 C518 119.5(3) . . ? C513 C518 C517 118.1(3) . . ? C16 N11 N12 119.2(2) . . ? C13 N12 N11 120.7(2) . . ? C17 N18 C19 117.4(2) . . ? C36 N31 N32 119.4(2) . . ? N31 N32 C33 121.0(2) . . ? C37 N38 C39 117.0(3) . . ? C56 N51 N52 119.32(18) . . ? C53 N52 N51 120.83(19) . . ? C59 N58 C57 117.0(2) . . ? C115 N114 C113 117.1(3) . . ? C313 N314 C315 116.9(3) . . ? C513 N514 C515 117.2(3) . . ? C74 O71 C72 99.0(9) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.15 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.712 _refine_diff_density_min -0.286 _refine_diff_density_rms 0.050 # Attachment '1_corrected.txt' data_1 _database_code_depnum_ccdc_archive 'CCDC 693497' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 4-Phenyl-3,6-Di(2-pyridyl)pyridazine _chemical_melting_point ? _chemical_formula_moiety 'C20 H14 N4' _chemical_formula_sum 'C20 H14 N4' _chemical_formula_weight 310.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/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 6.164(6) _cell_length_b 14.713(1) _cell_length_c 17.365(1) _cell_angle_alpha 90.00 _cell_angle_beta 95.380(1) _cell_angle_gamma 90.00 _cell_volume 1567.9(15) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 3366 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 24.81 _exptl_crystal_description Blocks _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.315 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type 'multi scan' _exptl_absorpt_correction_T_min 0.9824 _exptl_absorpt_correction_T_max 0.9904 _exptl_absorpt_process_details 'SADABS; Sheldrick, 1997' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16199 _diffrn_reflns_av_R_equivalents 0.0365 _diffrn_reflns_av_sigmaI/netI 0.0250 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 24.96 _reflns_number_total 2735 _reflns_number_gt 2184 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0507P)^2^+0.2637P] 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 2735 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0539 _refine_ls_R_factor_gt 0.0404 _refine_ls_wR_factor_ref 0.1043 _refine_ls_wR_factor_gt 0.0974 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _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 0.0741(2) 0.84274(10) 0.03501(8) 0.0394(4) Uani 1 1 d . . . C2 C -0.0940(3) 0.83871(11) -0.02400(9) 0.0494(4) Uani 1 1 d . . . H2 H -0.2281 0.8146 -0.0142 0.059 Uiso 1 1 calc R . . C3 C -0.0636(3) 0.87026(13) -0.09732(9) 0.0583(5) Uani 1 1 d . . . H3 H -0.1763 0.8662 -0.1367 0.070 Uiso 1 1 calc R . . C4 C 0.1332(3) 0.90767(11) -0.11216(10) 0.0590(5) Uani 1 1 d . . . H4 H 0.1530 0.9291 -0.1614 0.071 Uiso 1 1 calc R . . C5 C 0.3002(3) 0.91318(12) -0.05389(10) 0.0584(5) Uani 1 1 d . . . H5 H 0.4329 0.9387 -0.0637 0.070 Uiso 1 1 calc R . . C6 C 0.2712(3) 0.88080(11) 0.01925(10) 0.0513(4) Uani 1 1 d . . . H6 H 0.3849 0.8846 0.0583 0.062 Uiso 1 1 calc R . . C13 C 0.1611(2) 0.74571(10) 0.15784(8) 0.0392(4) Uani 1 1 d . . . C14 C 0.0360(2) 0.81195(10) 0.11448(8) 0.0374(3) Uani 1 1 d . . . C15 C -0.1289(2) 0.85121(10) 0.15152(8) 0.0402(4) Uani 1 1 d . . . H15 H -0.2207 0.8937 0.1257 0.048 Uiso 1 1 calc R . . C16 C -0.1584(2) 0.82750(10) 0.22745(8) 0.0391(4) Uani 1 1 d . . . C17 C 0.3387(2) 0.69045(10) 0.12781(8) 0.0397(4) Uani 1 1 d . . . C19 C 0.4816(3) 0.62204(13) 0.02597(11) 0.0653(5) Uani 1 1 d . . . H19 H 0.4716 0.6081 -0.0265 0.078 Uiso 1 1 calc R . . C110 C 0.6612(3) 0.59141(12) 0.07136(11) 0.0603(5) Uani 1 1 d . . . H110 H 0.7701 0.5588 0.0500 0.072 Uiso 1 1 calc R . . C111 C 0.6758(3) 0.61020(11) 0.14918(11) 0.0522(4) Uani 1 1 d . . . H111 H 0.7935 0.5894 0.1818 0.063 Uiso 1 1 calc R . . C112 C 0.5127(2) 0.66047(10) 0.17807(9) 0.0439(4) Uani 1 1 d . . . H112 H 0.5191 0.6741 0.2305 0.053 Uiso 1 1 calc R . . C113 C -0.3367(2) 0.86760(10) 0.26950(8) 0.0402(4) Uani 1 1 d . . . C115 C -0.6316(3) 0.96243(12) 0.26463(11) 0.0579(5) Uani 1 1 d . . . H115 H -0.7247 1.0031 0.2371 0.069 Uiso 1 1 calc R . . C116 C -0.6703(3) 0.94288(12) 0.33973(11) 0.0582(5) Uani 1 1 d . . . H116 H -0.7849 0.9701 0.3623 0.070 Uiso 1 1 calc R . . C117 C -0.5349(3) 0.88211(12) 0.38038(11) 0.0599(5) Uani 1 1 d . . . H117 H -0.5568 0.8670 0.4311 0.072 Uiso 1 1 calc R . . C118 C -0.3656(3) 0.84379(11) 0.34489(9) 0.0503(4) Uani 1 1 d . . . H118 H -0.2720 0.8024 0.3714 0.060 Uiso 1 1 calc R . . N11 N -0.0290(2) 0.76707(9) 0.26711(7) 0.0470(3) Uani 1 1 d . . . N12 N 0.1283(2) 0.72576(9) 0.23152(7) 0.0458(3) Uani 1 1 d . . . N18 N 0.3198(2) 0.67059(9) 0.05209(7) 0.0541(4) Uani 1 1 d . . . N114 N -0.4685(2) 0.92650(10) 0.22874(8) 0.0517(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0430(9) 0.0364(8) 0.0385(8) 0.0002(6) 0.0023(7) 0.0047(7) C2 0.0477(10) 0.0553(10) 0.0443(9) 0.0014(7) -0.0007(7) 0.0014(8) C3 0.0706(13) 0.0635(11) 0.0386(9) 0.0016(8) -0.0063(8) 0.0023(10) C4 0.0892(15) 0.0493(10) 0.0395(9) 0.0038(7) 0.0121(10) -0.0016(9) C5 0.0643(12) 0.0545(10) 0.0581(11) 0.0052(8) 0.0158(9) -0.0104(9) C6 0.0476(10) 0.0559(10) 0.0494(10) 0.0042(8) -0.0011(7) -0.0051(8) C13 0.0381(8) 0.0387(8) 0.0395(8) 0.0002(6) -0.0027(6) -0.0027(7) C14 0.0362(8) 0.0370(8) 0.0381(8) -0.0012(6) -0.0015(6) -0.0028(6) C15 0.0393(8) 0.0381(8) 0.0419(8) 0.0028(6) -0.0032(7) 0.0012(7) C16 0.0391(8) 0.0373(8) 0.0402(8) -0.0012(6) -0.0002(7) -0.0039(7) C17 0.0414(9) 0.0338(8) 0.0435(8) 0.0019(6) 0.0019(7) -0.0021(6) C19 0.0828(14) 0.0653(12) 0.0487(10) -0.0061(9) 0.0105(10) 0.0215(11) C110 0.0578(11) 0.0536(10) 0.0721(13) 0.0044(9) 0.0196(9) 0.0152(9) C111 0.0409(9) 0.0473(9) 0.0679(12) 0.0086(8) 0.0021(8) 0.0045(7) C112 0.0417(9) 0.0426(9) 0.0466(9) 0.0032(7) -0.0002(7) -0.0007(7) C113 0.0402(8) 0.0384(8) 0.0416(8) -0.0038(7) 0.0019(7) -0.0045(7) C115 0.0468(10) 0.0581(11) 0.0692(12) 0.0043(9) 0.0076(9) 0.0109(8) C116 0.0543(11) 0.0540(10) 0.0689(12) -0.0065(9) 0.0201(9) 0.0037(9) C117 0.0724(12) 0.0583(11) 0.0521(10) -0.0007(8) 0.0213(9) 0.0030(10) C118 0.0566(10) 0.0481(9) 0.0465(10) 0.0002(7) 0.0068(8) 0.0041(8) N11 0.0464(8) 0.0530(8) 0.0415(7) 0.0024(6) 0.0041(6) 0.0055(7) N12 0.0447(8) 0.0508(8) 0.0414(7) 0.0044(6) 0.0019(6) 0.0064(6) N18 0.0629(9) 0.0544(9) 0.0442(8) -0.0046(6) 0.0013(7) 0.0143(7) N114 0.0473(8) 0.0556(8) 0.0521(8) 0.0039(7) 0.0047(6) 0.0078(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.388(2) . ? C1 C2 1.389(2) . ? C1 C14 1.492(2) . ? C2 C3 1.384(2) . ? C3 C4 1.378(3) . ? C4 C5 1.377(3) . ? C5 C6 1.384(2) . ? C13 N12 1.3461(18) . ? C13 C14 1.415(2) . ? C13 C17 1.497(2) . ? C14 C15 1.380(2) . ? C15 C16 1.392(2) . ? C16 N11 1.3410(19) . ? C16 C113 1.496(2) . ? C17 N18 1.3412(19) . ? C17 C112 1.389(2) . ? C19 N18 1.340(2) . ? C19 C110 1.373(3) . ? C110 C111 1.374(3) . ? C111 C112 1.380(2) . ? C113 N114 1.343(2) . ? C113 C118 1.383(2) . ? C115 N114 1.340(2) . ? C115 C116 1.378(2) . ? C116 C117 1.373(3) . ? C117 C118 1.381(2) . ? N11 N12 1.3433(19) . ? 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 C1 C2 118.57(15) . . ? C6 C1 C14 121.43(13) . . ? C2 C1 C14 119.89(14) . . ? C3 C2 C1 120.54(16) . . ? C4 C3 C2 120.23(17) . . ? C5 C4 C3 119.79(16) . . ? C4 C5 C6 120.14(17) . . ? C5 C6 C1 120.71(16) . . ? N12 C13 C14 122.24(14) . . ? N12 C13 C17 113.11(13) . . ? C14 C13 C17 124.65(13) . . ? C15 C14 C13 115.38(13) . . ? C15 C14 C1 119.40(13) . . ? C13 C14 C1 125.20(13) . . ? C14 C15 C16 120.28(14) . . ? N11 C16 C15 121.87(14) . . ? N11 C16 C113 116.08(13) . . ? C15 C16 C113 122.05(14) . . ? N18 C17 C112 122.53(14) . . ? N18 C17 C13 117.44(13) . . ? C112 C17 C13 120.03(14) . . ? N18 C19 C110 124.49(17) . . ? C19 C110 C111 118.24(17) . . ? C110 C111 C112 118.87(16) . . ? C111 C112 C17 119.17(16) . . ? N114 C113 C118 122.48(15) . . ? N114 C113 C16 115.65(13) . . ? C118 C113 C16 121.85(14) . . ? N114 C115 C116 124.16(17) . . ? C117 C116 C115 118.17(16) . . ? C116 C117 C118 119.01(17) . . ? C117 C118 C113 119.26(16) . . ? C16 N11 N12 118.96(13) . . ? N11 N12 C13 121.17(13) . . ? C19 N18 C17 116.67(15) . . ? C115 N114 C113 116.91(15) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 24.96 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.151 _refine_diff_density_min -0.155 _refine_diff_density_rms 0.029 # Attachment '2_corrected.txt' data_2 _database_code_depnum_ccdc_archive 'CCDC 719943' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C34 H22 N8' _chemical_formula_sum 'C34 H22 N8' _chemical_formula_weight 542.60 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' _symmetry_cell_setting Trigonal _symmetry_space_group_name_H-M 'R -3' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 36.000(1) _cell_length_b 36.000(1) _cell_length_c 6.213(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 6973(6) _cell_formula_units_Z 9 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 6751 _cell_measurement_theta_min 2.26 _cell_measurement_theta_max 24.99 _exptl_crystal_description Blocks _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.163 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2538 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_type 'multi scan' _exptl_absorpt_correction_T_min 0.9842 _exptl_absorpt_correction_T_max 0.9914 _exptl_absorpt_process_details 'SADABS; Sheldrick, 1997' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23138 _diffrn_reflns_av_R_equivalents 0.0436 _diffrn_reflns_av_sigmaI/netI 0.0247 _diffrn_reflns_limit_h_min -42 _diffrn_reflns_limit_h_max 42 _diffrn_reflns_limit_k_min -42 _diffrn_reflns_limit_k_max 42 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2723 _reflns_number_gt 2320 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0695P)^2^+3.1129P] 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 2723 _refine_ls_number_parameters 194 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0498 _refine_ls_R_factor_gt 0.0408 _refine_ls_wR_factor_ref 0.1125 _refine_ls_wR_factor_gt 0.1077 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _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 0.36814(4) 0.16156(4) 0.6086(2) 0.0220(3) Uani 1 1 d . . . C2 C 0.34906(4) 0.14851(4) 0.8101(2) 0.0247(3) Uani 1 1 d . . . H2A H 0.3596 0.1359 0.9090 0.030 Uiso 1 1 calc R . . C3 C 0.31493(4) 0.15376(4) 0.8676(2) 0.0241(3) Uani 1 1 d . . . H3A H 0.3025 0.1450 1.0064 0.029 Uiso 1 1 calc R . . C13 C 0.44165(4) 0.16556(4) 0.6442(2) 0.0231(3) Uani 1 1 d . . . C14 C 0.40223(4) 0.15246(4) 0.5374(2) 0.0219(3) Uani 1 1 d . . . C15 C 0.39486(4) 0.12750(4) 0.3576(2) 0.0221(3) Uani 1 1 d . . . H15A H 0.3696 0.1187 0.2746 0.027 Uiso 1 1 calc R . . C16 C 0.42428(4) 0.11511(4) 0.2969(2) 0.0223(3) Uani 1 1 d . . . C17 C 0.45753(4) 0.19500(4) 0.8327(2) 0.0259(3) Uani 1 1 d . . . C19 C 0.45734(6) 0.24915(5) 1.0235(3) 0.0459(5) Uani 1 1 d . . . H19A H 0.4475 0.2691 1.0403 0.055 Uiso 1 1 calc R . . C110 C 0.48518(6) 0.24918(5) 1.1754(3) 0.0442(4) Uani 1 1 d . . . H11B H 0.4938 0.2682 1.2947 0.053 Uiso 1 1 calc R . . C111 C 0.50015(5) 0.22109(5) 1.1507(3) 0.0385(4) Uani 1 1 d . . . C112 C 0.48634(5) 0.19352(5) 0.9762(2) 0.0308(4) Uani 1 1 d . . . H11C H 0.4964 0.1739 0.9549 0.037 Uiso 1 1 calc R . . C113 C 0.41753(4) 0.08816(4) 0.1030(2) 0.0231(3) Uani 1 1 d . . . C115 C 0.37488(5) 0.05398(5) -0.1869(2) 0.0298(3) Uani 1 1 d . . . H11D H 0.3494 0.0458 -0.2663 0.036 Uiso 1 1 calc R . . C116 C 0.40305(5) 0.04172(5) -0.2644(2) 0.0309(4) Uani 1 1 d . . . H11E H 0.3972 0.0258 -0.3942 0.037 Uiso 1 1 calc R . . C117 C 0.44000(5) 0.05324(5) -0.1482(2) 0.0304(4) Uani 1 1 d . . . H11F H 0.4599 0.0451 -0.1961 0.037 Uiso 1 1 calc R . . C118 C 0.44754(5) 0.07681(4) 0.0384(2) 0.0284(3) Uani 1 1 d . . . H11G H 0.4727 0.0851 0.1211 0.034 Uiso 1 1 calc R . . N11 N 0.45996(4) 0.12673(4) 0.40986(18) 0.0271(3) Uani 1 1 d . . . N12 N 0.46859(4) 0.15237(4) 0.57995(18) 0.0271(3) Uani 1 1 d . . . N18 N 0.44321(4) 0.22279(4) 0.8535(2) 0.0369(3) Uani 1 1 d . . . N114 N 0.38131(4) 0.07669(4) -0.00690(18) 0.0264(3) Uani 1 1 d . . . H111 H 0.5196(6) 0.2201(5) 1.252(3) 0.045(5) 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 0.0254(7) 0.0204(7) 0.0220(7) -0.0033(5) -0.0043(5) 0.0128(6) C2 0.0333(8) 0.0270(7) 0.0210(7) -0.0015(5) -0.0049(6) 0.0205(6) C3 0.0313(8) 0.0266(7) 0.0179(7) -0.0001(5) 0.0000(6) 0.0172(6) C13 0.0271(7) 0.0214(7) 0.0233(7) 0.0030(5) -0.0006(6) 0.0141(6) C14 0.0265(7) 0.0205(7) 0.0207(7) 0.0033(5) 0.0003(5) 0.0132(6) C15 0.0237(7) 0.0248(7) 0.0202(7) 0.0016(5) -0.0019(5) 0.0139(6) C16 0.0247(7) 0.0226(7) 0.0213(7) 0.0037(5) 0.0011(5) 0.0131(6) C17 0.0271(7) 0.0219(7) 0.0274(7) -0.0006(6) -0.0016(6) 0.0113(6) C19 0.0523(11) 0.0347(9) 0.0580(11) -0.0207(8) -0.0183(9) 0.0273(8) C110 0.0513(10) 0.0345(9) 0.0440(10) -0.0176(7) -0.0138(8) 0.0192(8) C111 0.0427(9) 0.0356(9) 0.0344(9) -0.0056(7) -0.0147(7) 0.0173(8) C112 0.0341(8) 0.0281(8) 0.0313(8) -0.0023(6) -0.0064(6) 0.0166(7) C113 0.0267(7) 0.0234(7) 0.0217(7) 0.0039(5) 0.0016(5) 0.0143(6) C115 0.0395(8) 0.0293(8) 0.0241(7) -0.0012(6) -0.0056(6) 0.0199(7) C116 0.0465(9) 0.0263(8) 0.0212(7) 0.0004(6) 0.0022(6) 0.0192(7) C117 0.0378(8) 0.0282(8) 0.0308(8) 0.0021(6) 0.0094(6) 0.0207(7) C118 0.0294(8) 0.0287(8) 0.0301(8) 0.0003(6) 0.0011(6) 0.0168(6) N11 0.0302(6) 0.0327(7) 0.0244(6) -0.0031(5) -0.0035(5) 0.0204(5) N12 0.0295(7) 0.0305(7) 0.0255(6) -0.0024(5) -0.0040(5) 0.0181(6) N18 0.0419(8) 0.0287(7) 0.0457(8) -0.0123(6) -0.0133(6) 0.0219(6) N114 0.0328(7) 0.0282(6) 0.0232(6) -0.0014(5) -0.0036(5) 0.0191(5) _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 C2 1.392(2) . ? C1 C3 1.3930(19) 13_556 ? C1 C14 1.4869(18) . ? C2 C3 1.3803(19) . ? C3 C1 1.3930(19) 13_556 ? C13 N12 1.3361(18) . ? C13 C14 1.4168(19) . ? C13 C17 1.489(2) . ? C14 C15 1.374(2) . ? C15 C16 1.3911(19) . ? C16 N11 1.3343(18) . ? C16 C113 1.489(2) . ? C17 N18 1.3413(18) . ? C17 C112 1.389(2) . ? C19 N18 1.339(2) . ? C19 C110 1.377(2) . ? C110 C111 1.372(2) . ? C111 C112 1.383(2) . ? C113 N114 1.3413(18) . ? C113 C118 1.3915(19) . ? C115 N114 1.335(2) . ? C115 C116 1.379(2) . ? C116 C117 1.382(2) . ? C117 C118 1.382(2) . ? N11 N12 1.3338(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 C2 C1 C3 118.54(13) . 13_556 ? C2 C1 C14 121.02(11) . . ? C3 C1 C14 120.13(12) 13_556 . ? C3 C2 C1 120.62(12) . . ? C2 C3 C1 120.84(13) . 13_556 ? N12 C13 C14 121.73(12) . . ? N12 C13 C17 113.53(11) . . ? C14 C13 C17 124.73(12) . . ? C15 C14 C13 115.62(12) . . ? C15 C14 C1 118.37(12) . . ? C13 C14 C1 125.94(12) . . ? C14 C15 C16 120.05(12) . . ? N11 C16 C15 121.69(12) . . ? N11 C16 C113 116.58(12) . . ? C15 C16 C113 121.73(12) . . ? N18 C17 C112 122.68(13) . . ? N18 C17 C13 116.90(12) . . ? C112 C17 C13 120.41(12) . . ? N18 C19 C110 124.05(15) . . ? C111 C110 C19 118.49(15) . . ? C110 C111 C112 118.94(15) . . ? C111 C112 C17 118.88(14) . . ? N114 C113 C118 122.74(13) . . ? N114 C113 C16 115.43(12) . . ? C118 C113 C16 121.81(12) . . ? N114 C115 C116 123.94(13) . . ? C115 C116 C117 118.22(14) . . ? C118 C117 C116 119.12(13) . . ? C117 C118 C113 118.66(13) . . ? N12 N11 C16 119.20(11) . . ? N11 N12 C13 121.57(11) . . ? C19 N18 C17 116.94(13) . . ? C115 N114 C113 117.32(12) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.240 _refine_diff_density_min -0.160 _refine_diff_density_rms 0.042 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.000 -0.013 418 14 ' ' 2 0.333 0.667 0.031 422 14 ' ' 3 0.667 0.333 0.698 422 14 ' ' _platon_squeeze_details ; ;