Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 186 _publ_requested_journal 'Dalton Transactions' loop_ _publ_author_name 'Browne, Wesley R.' 'Hughes, Donal' 'James, P.' 'Lynch, Fiona C.' 'Maestri, M.' 'Nieuwenhuyzen, Mark' 'Passaniti, P.' 'Vos, J.' _publ_contact_author_name 'Dr J Vos' _publ_contact_author_address ; Dr J Vos School of Chemical Sciences Dublin City University Dublin 9 IRELAND ; _publ_contact_author_email 'JOHANNES.VOS@DCU.IE' _publ_section_title ; Synthesis, spectroscopic and electrochemical properties of mononuclear and dinuclear bis(bipy)ruthenium(II) complexes containing dimethoxyphenyl-(pyridin-2-yl)1,2,4-triazole ligands. ; data_donal2 _database_code_CSD 171755 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H35 F6 N8 O3 P Ru' _chemical_formula_weight 897.78 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'P' 'P' 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Ru' 'Ru' -1.2594 0.8363 '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 11.704(7) _cell_length_b 12.915(7) _cell_length_c 15.631(9) _cell_angle_alpha 69.920(10) _cell_angle_beta 88.600(10) _cell_angle_gamma 63.140(10) _cell_volume 1955.5(19) _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 needle _exptl_crystal_colour red _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.525 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 912 _exptl_absorpt_coefficient_mu 0.519 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.7599 _exptl_absorpt_correction_T_max 0.9170 _exptl_absorpt_process_details 'Psi Scans' _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 'Siemens P4' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7006 _diffrn_reflns_av_R_equivalents 0.0501 _diffrn_reflns_av_sigmaI/netI 0.0555 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.40 _diffrn_reflns_theta_max 22.18 _reflns_number_total 4917 _reflns_number_gt 4221 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.0866P)^2^+8.9749P] 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 4917 _refine_ls_number_parameters 489 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0761 _refine_ls_R_factor_gt 0.0655 _refine_ls_wR_factor_ref 0.1724 _refine_ls_wR_factor_gt 0.1639 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.090 _refine_ls_shift/su_mean 0.005 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 Ru1 Ru 0.14793(5) 0.36406(5) 0.25434(4) 0.0271(2) Uani 1 1 d . . . N1 N 0.1616(6) 0.2807(5) 0.1614(4) 0.0368(15) Uani 1 1 d . . . C2 C 0.1715(8) 0.1671(7) 0.1783(6) 0.046(2) Uani 1 1 d . . . H2 H 0.1641 0.1223 0.2372 0.055 Uiso 1 1 calc R . . C3 C 0.1918(9) 0.1146(8) 0.1132(6) 0.055(2) Uani 1 1 d . . . H3 H 0.1991 0.0354 0.1283 0.066 Uiso 1 1 calc R . . C4 C 0.2014(9) 0.1792(8) 0.0257(7) 0.056(2) Uani 1 1 d . . . H4 H 0.2159 0.1442 -0.0191 0.067 Uiso 1 1 calc R . . C5 C 0.1892(8) 0.2978(8) 0.0047(6) 0.047(2) Uani 1 1 d . . . H5 H 0.1942 0.3440 -0.0545 0.057 Uiso 1 1 calc R . . C6 C 0.1694(7) 0.3455(7) 0.0735(5) 0.0373(18) Uani 1 1 d . . . C7 C 0.1515(7) 0.4726(7) 0.0584(5) 0.0346(17) Uani 1 1 d . . . C8 C 0.1578(8) 0.5520(8) -0.0249(5) 0.046(2) Uani 1 1 d . . . H8 H 0.1743 0.5271 -0.0750 0.055 Uiso 1 1 calc R . . C9 C 0.1397(9) 0.6688(8) -0.0335(6) 0.053(2) Uani 1 1 d . . . H9 H 0.1441 0.7231 -0.0892 0.064 Uiso 1 1 calc R . . C10 C 0.1145(8) 0.7036(8) 0.0429(6) 0.051(2) Uani 1 1 d . . . H10 H 0.1023 0.7814 0.0393 0.062 Uiso 1 1 calc R . . C11 C 0.1082(7) 0.6203(7) 0.1238(6) 0.0431(19) Uani 1 1 d . . . H11 H 0.0889 0.6452 0.1739 0.052 Uiso 1 1 calc R . . N12 N 0.1285(6) 0.5040(5) 0.1349(4) 0.0354(14) Uani 1 1 d . . . N13 N 0.1510(6) 0.4567(5) 0.3375(4) 0.0389(15) Uani 1 1 d . . . C14 C 0.0464(9) 0.5309(7) 0.3666(6) 0.050(2) Uani 1 1 d . . . H14 H -0.0349 0.5423 0.3486 0.060 Uiso 1 1 calc R . . C15 C 0.0571(10) 0.5896(8) 0.4219(6) 0.056(2) Uani 1 1 d . . . H15 H -0.0164 0.6414 0.4399 0.067 Uiso 1 1 calc R . . C16 C 0.1776(11) 0.5711(8) 0.4506(6) 0.061(3) Uani 1 1 d . . . H16 H 0.1864 0.6093 0.4889 0.073 Uiso 1 1 calc R . . C17 C 0.2848(9) 0.4955(8) 0.4219(6) 0.055(2) Uani 1 1 d . . . H17 H 0.3669 0.4816 0.4408 0.066 Uiso 1 1 calc R . . C18 C 0.2683(7) 0.4409(7) 0.3650(5) 0.0384(18) Uani 1 1 d . . . C19 C 0.3762(7) 0.3644(7) 0.3255(5) 0.0380(18) Uani 1 1 d . . . C20 C 0.5012(8) 0.3457(8) 0.3380(6) 0.054(2) Uani 1 1 d . . . H20 H 0.5229 0.3786 0.3755 0.065 Uiso 1 1 calc R . . C21 C 0.5928(9) 0.2792(8) 0.2956(7) 0.058(2) Uani 1 1 d . . . H21 H 0.6773 0.2662 0.3041 0.070 Uiso 1 1 calc R . . C22 C 0.5592(8) 0.2316(8) 0.2404(6) 0.055(2) Uani 1 1 d . . . H22 H 0.6199 0.1875 0.2096 0.066 Uiso 1 1 calc R . . C23 C 0.4342(7) 0.2502(7) 0.2314(5) 0.046(2) Uani 1 1 d . . . H23 H 0.4135 0.2140 0.1962 0.055 Uiso 1 1 calc R . . N24 N 0.3402(6) 0.3174(5) 0.2702(4) 0.0355(14) Uani 1 1 d . . . N25 N 0.1649(6) 0.2146(5) 0.3723(4) 0.0386(15) Uani 1 1 d . . . C26 C 0.2754(8) 0.1174(7) 0.4247(6) 0.047(2) Uani 1 1 d . . . H26 H 0.3538 0.1102 0.4060 0.056 Uiso 1 1 calc R . . C27 C 0.2773(9) 0.0283(8) 0.5046(6) 0.059(2) Uani 1 1 d . . . H27 H 0.3559 -0.0376 0.5393 0.071 Uiso 1 1 calc R . . C28 C 0.1628(9) 0.0369(8) 0.5329(6) 0.054(2) Uani 1 1 d . . . H28 H 0.1632 -0.0223 0.5876 0.065 Uiso 1 1 calc R . . C29 C 0.0490(9) 0.1324(8) 0.4808(6) 0.052(2) Uani 1 1 d . . . H29 H -0.0293 0.1382 0.4987 0.063 Uiso 1 1 calc R . . C30 C 0.0505(7) 0.2211(7) 0.4005(5) 0.0386(18) Uani 1 1 d . . . C31 C -0.0620(7) 0.3306(7) 0.3379(5) 0.0360(18) Uani 1 1 d . . . N32 N -0.0432(6) 0.4060(5) 0.2624(4) 0.0317(14) Uani 1 1 d . . . N33 N -0.1623(6) 0.5042(6) 0.2197(4) 0.0386(15) Uani 1 1 d . . . C34 C -0.2447(7) 0.4793(7) 0.2739(5) 0.0371(18) Uani 1 1 d . . . N35 N -0.1880(6) 0.3714(6) 0.3492(4) 0.0405(15) Uani 1 1 d . . . C36 C -0.3856(7) 0.5682(7) 0.2605(5) 0.0410(19) Uani 1 1 d . . . C37 C -0.4363(7) 0.5914(8) 0.3364(6) 0.044(2) Uani 1 1 d . . . H37 H -0.3823 0.5488 0.3931 0.053 Uiso 1 1 calc R . . C38 C -0.5636(8) 0.6750(8) 0.3315(6) 0.048(2) Uani 1 1 d . . . C39 C -0.6459(8) 0.7349(9) 0.2493(7) 0.061(3) Uani 1 1 d . . . H39 H -0.7327 0.7905 0.2454 0.073 Uiso 1 1 calc R . . C40 C -0.5978(8) 0.7114(9) 0.1715(7) 0.065(3) Uani 1 1 d . . . H40 H -0.6531 0.7523 0.1155 0.078 Uiso 1 1 calc R . . C41 C -0.4681(8) 0.6273(9) 0.1766(6) 0.054(2) Uani 1 1 d . . . O42 O -0.6005(6) 0.6893(6) 0.4128(5) 0.0686(18) Uani 1 1 d . . . C43 C -0.7124(10) 0.8002(10) 0.4075(9) 0.086(4) Uani 1 1 d . . . H43A H -0.7270 0.7984 0.4686 0.129 Uiso 1 1 calc R . . H43B H -0.7860 0.8064 0.3761 0.129 Uiso 1 1 calc R . . H43C H -0.7000 0.8712 0.3741 0.129 Uiso 1 1 calc R . . O44 O -0.4149(6) 0.6000(7) 0.1034(4) 0.077(2) Uani 1 1 d . . . C45 C -0.4997(12) 0.6575(16) 0.0180(8) 0.130(6) Uani 1 1 d . . . H45A H -0.4512 0.6318 -0.0280 0.195 Uiso 1 1 calc R . . H45B H -0.5385 0.7468 -0.0013 0.195 Uiso 1 1 calc R . . H45C H -0.5663 0.6326 0.0257 0.195 Uiso 1 1 calc R . . P1 P -0.0837(2) 0.9613(2) 0.19211(19) 0.0598(11) Uani 0.158(9) 1 d P A 2 F11 F -0.168(5) 1.026(5) 0.089(4) 0.109(16) Uiso 0.158(9) 1 d P A 2 F12 F -0.129(3) 1.095(2) 0.2113(17) 0.035(7) Uiso 0.158(9) 1 d P A 2 F13 F 0.060(4) 0.900(4) 0.161(3) 0.075(11) Uiso 0.158(9) 1 d P A 2 F14 F 0.003(3) 0.876(3) 0.299(2) 0.046(8) Uiso 0.158(9) 1 d P A 2 F15 F -0.067(3) 0.831(3) 0.197(2) 0.054(9) Uiso 0.158(9) 1 d P A 2 F16 F -0.236(4) 0.999(4) 0.213(3) 0.085(12) Uiso 0.158(9) 1 d P A 2 P1' P -0.0837(2) 0.9613(2) 0.19211(19) 0.0598(11) Uani 0.84 1 d P A 1 F11' F -0.1909(12) 1.0837(12) 0.1194(8) 0.147(4) Uiso 0.842(9) 1 d P A 1 F12' F -0.0456(15) 1.0419(13) 0.2280(9) 0.165(5) Uiso 0.842(9) 1 d P A 1 F13' F 0.0127(12) 0.9724(13) 0.1227(9) 0.144(4) Uiso 0.842(9) 1 d P A 1 F14' F 0.0243(14) 0.8391(14) 0.2614(10) 0.175(5) Uiso 0.842(9) 1 d P A 1 F15' F -0.1186(12) 0.8797(11) 0.1523(9) 0.130(4) Uiso 0.842(9) 1 d P A 1 F16' F -0.1834(9) 0.9596(9) 0.2627(7) 0.100(3) Uiso 0.842(9) 1 d P A 1 C1S C -0.4252(14) 0.8894(14) 0.2909(10) 0.102(4) Uiso 1 1 d . . . O1S O -0.5124(15) 0.9596(14) 0.3204(10) 0.180(5) Uiso 1 1 d . . . C2S C -0.3114(14) 0.7843(14) 0.3617(10) 0.119(5) Uiso 1 1 d . . . H2SA H -0.3266 0.7878 0.4215 0.179 Uiso 1 1 calc R . . H2SB H -0.2347 0.7920 0.3472 0.179 Uiso 1 1 calc R . . H2SC H -0.2999 0.7059 0.3616 0.179 Uiso 1 1 calc R . . C3S C -0.4287(15) 0.9069(15) 0.1974(10) 0.124(5) Uiso 1 1 d . . . H3SA H -0.5091 0.9780 0.1632 0.185 Uiso 1 1 calc R . . H3SB H -0.4217 0.8338 0.1897 0.185 Uiso 1 1 calc R . . H3SC H -0.3577 0.9209 0.1753 0.185 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 Ru1 0.0240(3) 0.0247(3) 0.0314(4) -0.0113(2) 0.0061(2) -0.0100(3) N1 0.029(3) 0.035(4) 0.046(4) -0.016(3) 0.005(3) -0.015(3) C2 0.054(5) 0.030(4) 0.053(5) -0.014(4) 0.003(4) -0.020(4) C3 0.066(6) 0.041(5) 0.065(6) -0.025(5) 0.009(5) -0.028(5) C4 0.061(6) 0.052(5) 0.070(6) -0.042(5) 0.014(5) -0.025(5) C5 0.047(5) 0.052(5) 0.045(5) -0.024(4) 0.011(4) -0.022(4) C6 0.030(4) 0.039(4) 0.043(5) -0.014(4) 0.008(3) -0.017(3) C7 0.028(4) 0.033(4) 0.039(4) -0.011(3) 0.004(3) -0.013(3) C8 0.048(5) 0.052(5) 0.038(5) -0.017(4) 0.013(4) -0.024(4) C9 0.060(6) 0.041(5) 0.051(5) -0.007(4) 0.015(4) -0.026(4) C10 0.057(6) 0.037(5) 0.058(6) -0.010(4) 0.009(4) -0.026(4) C11 0.043(5) 0.035(4) 0.051(5) -0.022(4) 0.004(4) -0.013(4) N12 0.032(3) 0.031(3) 0.044(4) -0.016(3) 0.008(3) -0.014(3) N13 0.044(4) 0.031(3) 0.035(3) -0.010(3) 0.006(3) -0.014(3) C14 0.054(5) 0.040(5) 0.052(5) -0.021(4) 0.014(4) -0.016(4) C15 0.072(7) 0.048(5) 0.057(5) -0.032(5) 0.020(5) -0.028(5) C16 0.095(8) 0.051(5) 0.048(5) -0.024(4) 0.008(5) -0.039(6) C17 0.062(6) 0.058(6) 0.055(5) -0.022(5) 0.008(5) -0.036(5) C18 0.042(5) 0.035(4) 0.033(4) -0.009(3) -0.002(3) -0.017(4) C19 0.037(5) 0.030(4) 0.043(4) -0.006(3) 0.001(4) -0.018(4) C20 0.041(5) 0.045(5) 0.073(6) -0.017(5) -0.002(4) -0.021(4) C21 0.043(5) 0.048(5) 0.079(7) -0.010(5) 0.000(5) -0.028(5) C22 0.029(5) 0.044(5) 0.076(6) -0.014(5) 0.013(4) -0.009(4) C23 0.038(5) 0.040(5) 0.047(5) -0.015(4) 0.002(4) -0.010(4) N24 0.037(4) 0.026(3) 0.035(3) -0.007(3) 0.007(3) -0.012(3) N25 0.035(4) 0.030(3) 0.046(4) -0.015(3) 0.005(3) -0.011(3) C26 0.037(5) 0.038(5) 0.054(5) -0.017(4) 0.003(4) -0.008(4) C27 0.057(6) 0.036(5) 0.060(6) -0.007(4) -0.005(5) -0.009(4) C28 0.068(7) 0.034(5) 0.048(5) -0.006(4) 0.012(5) -0.021(5) C29 0.055(6) 0.046(5) 0.054(5) -0.016(4) 0.024(5) -0.026(5) C30 0.035(4) 0.034(4) 0.051(5) -0.020(4) 0.013(4) -0.017(4) C31 0.029(4) 0.033(4) 0.045(5) -0.017(4) 0.009(3) -0.012(3) N32 0.036(4) 0.023(3) 0.030(3) -0.009(3) 0.001(3) -0.009(3) N33 0.036(4) 0.039(4) 0.046(4) -0.021(3) 0.012(3) -0.017(3) C34 0.033(4) 0.038(4) 0.042(4) -0.021(4) 0.008(4) -0.015(4) N35 0.038(4) 0.037(4) 0.044(4) -0.015(3) 0.012(3) -0.016(3) C36 0.030(4) 0.044(5) 0.049(5) -0.017(4) 0.013(4) -0.018(4) C37 0.035(5) 0.053(5) 0.048(5) -0.022(4) 0.011(4) -0.020(4) C38 0.041(5) 0.051(5) 0.064(6) -0.032(5) 0.021(4) -0.024(4) C39 0.025(5) 0.063(6) 0.087(7) -0.031(5) 0.012(5) -0.012(4) C40 0.035(5) 0.079(7) 0.063(6) -0.018(5) -0.006(4) -0.017(5) C41 0.033(5) 0.066(6) 0.057(6) -0.023(5) 0.009(4) -0.018(4) O42 0.050(4) 0.082(5) 0.082(5) -0.051(4) 0.026(3) -0.023(4) C43 0.069(7) 0.075(7) 0.121(10) -0.064(7) 0.040(7) -0.020(6) O44 0.045(4) 0.118(6) 0.056(4) -0.041(4) 0.009(3) -0.023(4) C45 0.069(8) 0.213(17) 0.066(8) -0.061(10) -0.004(6) -0.026(10) P1 0.0534(17) 0.0439(16) 0.079(2) -0.0193(13) 0.0194(13) -0.0233(13) P1' 0.0534(17) 0.0439(16) 0.079(2) -0.0193(13) 0.0194(13) -0.0233(13) _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 Ru1 N12 2.034(6) . ? Ru1 N24 2.047(6) . ? Ru1 N1 2.050(6) . ? Ru1 N13 2.057(6) . ? Ru1 N32 2.062(6) . ? Ru1 N25 2.096(6) . ? N1 C2 1.348(9) . ? N1 C6 1.368(9) . ? C2 C3 1.366(11) . ? C3 C4 1.368(12) . ? C4 C5 1.391(12) . ? C5 C6 1.380(11) . ? C6 C7 1.490(10) . ? C7 N12 1.372(9) . ? C7 C8 1.378(10) . ? C8 C9 1.381(11) . ? C9 C10 1.396(12) . ? C10 C11 1.376(11) . ? C11 N12 1.358(9) . ? N13 C18 1.352(10) . ? N13 C14 1.356(10) . ? C14 C15 1.370(12) . ? C15 C16 1.379(13) . ? C16 C17 1.376(13) . ? C17 C18 1.374(11) . ? C18 C19 1.486(11) . ? C19 N24 1.378(9) . ? C19 C20 1.378(11) . ? C20 C21 1.360(13) . ? C21 C22 1.371(13) . ? C22 C23 1.374(11) . ? C23 N24 1.341(10) . ? N25 C26 1.340(10) . ? N25 C30 1.375(9) . ? C26 C27 1.369(12) . ? C27 C28 1.369(12) . ? C28 C29 1.356(12) . ? C29 C30 1.385(11) . ? C30 C31 1.456(10) . ? C31 N32 1.335(9) . ? C31 N35 1.353(9) . ? N32 N33 1.365(8) . ? N33 C34 1.343(9) . ? C34 N35 1.358(9) . ? C34 C36 1.491(10) . ? C36 C37 1.378(11) . ? C36 C41 1.394(11) . ? C37 C38 1.374(11) . ? C38 C39 1.371(12) . ? C38 O42 1.379(10) . ? C39 C40 1.399(13) . ? C40 C41 1.395(12) . ? C41 O44 1.366(10) . ? O42 C43 1.414(11) . ? O44 C45 1.428(12) . ? P1 F15 1.58(3) . ? P1 F11 1.63(5) . ? P1 F13 1.65(4) . ? P1 F14 1.68(3) . ? P1 F16 1.68(4) . ? P1 F12 1.70(3) . ? C1S O1S 1.227(17) . ? C1S C3S 1.398(18) . ? C1S C2S 1.499(18) . ? 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 N12 Ru1 N24 86.2(2) . . ? N12 Ru1 N1 79.5(2) . . ? N24 Ru1 N1 94.9(2) . . ? N12 Ru1 N13 94.6(2) . . ? N24 Ru1 N13 79.1(2) . . ? N1 Ru1 N13 171.9(2) . . ? N12 Ru1 N32 101.0(2) . . ? N24 Ru1 N32 170.1(2) . . ? N1 Ru1 N32 93.2(2) . . ? N13 Ru1 N32 93.4(2) . . ? N12 Ru1 N25 176.3(2) . . ? N24 Ru1 N25 95.3(2) . . ? N1 Ru1 N25 97.0(2) . . ? N13 Ru1 N25 89.0(2) . . ? N32 Ru1 N25 78.0(2) . . ? C2 N1 C6 116.8(7) . . ? C2 N1 Ru1 127.5(5) . . ? C6 N1 Ru1 115.5(5) . . ? N1 C2 C3 123.2(8) . . ? C2 C3 C4 119.6(8) . . ? C3 C4 C5 119.1(8) . . ? C6 C5 C4 118.6(8) . . ? N1 C6 C5 122.6(7) . . ? N1 C6 C7 114.0(6) . . ? C5 C6 C7 123.3(7) . . ? N12 C7 C8 122.7(7) . . ? N12 C7 C6 114.2(6) . . ? C8 C7 C6 123.1(7) . . ? C7 C8 C9 119.7(7) . . ? C8 C9 C10 118.8(7) . . ? C11 C10 C9 118.5(8) . . ? N12 C11 C10 124.0(7) . . ? C11 N12 C7 116.3(6) . . ? C11 N12 Ru1 127.6(5) . . ? C7 N12 Ru1 115.7(5) . . ? C18 N13 C14 118.0(7) . . ? C18 N13 Ru1 116.3(5) . . ? C14 N13 Ru1 125.6(6) . . ? N13 C14 C15 121.9(9) . . ? C14 C15 C16 119.4(9) . . ? C17 C16 C15 119.3(8) . . ? C18 C17 C16 118.8(9) . . ? N13 C18 C17 122.5(8) . . ? N13 C18 C19 114.4(6) . . ? C17 C18 C19 123.1(7) . . ? N24 C19 C20 121.7(7) . . ? N24 C19 C18 114.4(6) . . ? C20 C19 C18 123.9(7) . . ? C21 C20 C19 120.1(9) . . ? C20 C21 C22 119.3(8) . . ? C21 C22 C23 118.7(8) . . ? N24 C23 C22 124.0(8) . . ? C23 N24 C19 116.3(7) . . ? C23 N24 Ru1 128.0(5) . . ? C19 N24 Ru1 115.7(5) . . ? C26 N25 C30 117.3(7) . . ? C26 N25 Ru1 126.6(5) . . ? C30 N25 Ru1 116.0(5) . . ? N25 C26 C27 122.7(8) . . ? C26 C27 C28 119.5(8) . . ? C29 C28 C27 119.6(8) . . ? C28 C29 C30 119.4(8) . . ? N25 C30 C29 121.5(7) . . ? N25 C30 C31 112.0(6) . . ? C29 C30 C31 126.5(7) . . ? N32 C31 N35 113.7(6) . . ? N32 C31 C30 118.8(6) . . ? N35 C31 C30 127.4(7) . . ? C31 N32 N33 106.9(6) . . ? C31 N32 Ru1 114.8(5) . . ? N33 N32 Ru1 137.1(5) . . ? C34 N33 N32 104.2(6) . . ? N33 C34 N35 114.9(6) . . ? N33 C34 C36 123.7(7) . . ? N35 C34 C36 121.1(7) . . ? C31 N35 C34 100.3(6) . . ? C37 C36 C41 118.7(7) . . ? C37 C36 C34 117.4(7) . . ? C41 C36 C34 124.0(7) . . ? C38 C37 C36 122.4(8) . . ? C39 C38 C37 119.6(8) . . ? C39 C38 O42 124.3(8) . . ? C37 C38 O42 116.1(8) . . ? C38 C39 C40 119.2(8) . . ? C41 C40 C39 120.9(8) . . ? O44 C41 C40 123.9(8) . . ? O44 C41 C36 117.0(7) . . ? C40 C41 C36 119.1(8) . . ? C38 O42 C43 118.0(8) . . ? C41 O44 C45 117.3(8) . . ? F15 P1 F11 89(2) . . ? F15 P1 F13 78.2(18) . . ? F11 P1 F13 97(2) . . ? F15 P1 F14 83.1(16) . . ? F11 P1 F14 172(2) . . ? F13 P1 F14 82.5(18) . . ? F15 P1 F16 88.4(18) . . ? F11 P1 F16 77(2) . . ? F13 P1 F16 165(2) . . ? F14 P1 F16 102.6(19) . . ? F15 P1 F12 163.0(14) . . ? F11 P1 F12 97(2) . . ? F13 P1 F12 116.6(17) . . ? F14 P1 F12 90.3(14) . . ? F16 P1 F12 77.7(17) . . ? O1S C1S C3S 122.9(15) . . ? O1S C1S C2S 115.5(15) . . ? C3S C1S C2S 121.6(14) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 22.18 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.861 _refine_diff_density_min -0.966 _refine_diff_density_rms 0.117 data_donal3 _database_code_CSD 171756 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H14 N4 O2' _chemical_formula_weight 282.30 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 P21/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 10.664(2) _cell_length_b 17.689(7) _cell_length_c 15.057(3) _cell_angle_alpha 90.00 _cell_angle_beta 96.96(1) _cell_angle_gamma 90.00 _cell_volume 2819.4(14) _cell_formula_units_Z 8 _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 0.85 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.330 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1184 _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 'Siemens P4' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3763 _diffrn_reflns_av_R_equivalents 0.0549 _diffrn_reflns_av_sigmaI/netI 0.0793 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 22.19 _reflns_number_total 3540 _reflns_number_gt 2259 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.0844P)^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 3540 _refine_ls_number_parameters 383 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1165 _refine_ls_R_factor_gt 0.0705 _refine_ls_wR_factor_ref 0.1868 _refine_ls_wR_factor_gt 0.1592 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _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 N1A N -0.0844(4) 0.1012(2) 0.5776(3) 0.0428(10) Uani 1 1 d . . . C2A C -0.1465(5) 0.1172(3) 0.4967(3) 0.0562(15) Uani 1 1 d . . . H2A H -0.1477 0.1671 0.4773 0.067 Uiso 1 1 calc R . . C3A C -0.2086(5) 0.0639(3) 0.4408(4) 0.0589(16) Uani 1 1 d . . . H3A H -0.2519 0.0780 0.3860 0.071 Uiso 1 1 calc R . . C4A C -0.2050(4) -0.0101(3) 0.4677(3) 0.0475(13) Uani 1 1 d . . . H4A H -0.2444 -0.0474 0.4307 0.057 Uiso 1 1 calc R . . C5A C -0.1424(4) -0.0286(3) 0.5503(3) 0.0410(12) Uani 1 1 d . . . H5A H -0.1400 -0.0784 0.5702 0.049 Uiso 1 1 calc R . . C6A C -0.0826(4) 0.0283(3) 0.6034(3) 0.0354(11) Uani 1 1 d . . . C7A C -0.0105(4) 0.0120(3) 0.6908(3) 0.0347(11) Uani 1 1 d . . . N8A N -0.0193(4) -0.0527(2) 0.7330(3) 0.0436(10) Uani 1 1 d . . . N9A N 0.0666(4) -0.0439(2) 0.8068(3) 0.0430(10) Uani 1 1 d . . . H9A H 0.0984 -0.0889 0.8607 0.052 Uiso 1 1 d R . . N10A N 0.0751(3) 0.0617(2) 0.7316(2) 0.0363(9) Uani 1 1 d . . . C11A C 0.1234(4) 0.0240(3) 0.8048(3) 0.0367(11) Uani 1 1 d . . . C12A C 0.2269(4) 0.0525(3) 0.8693(3) 0.0402(12) Uani 1 1 d . . . C13A C 0.3030(5) 0.1094(3) 0.8393(3) 0.0490(14) Uani 1 1 d . . . H13A H 0.2848 0.1283 0.7815 0.059 Uiso 1 1 calc R . . C14A C 0.4053(5) 0.1378(3) 0.8951(4) 0.0568(15) Uani 1 1 d . . . C15A C 0.4330(6) 0.1078(3) 0.9796(4) 0.0659(17) Uani 1 1 d . . . H15A H 0.5037 0.1251 1.0162 0.079 Uiso 1 1 calc R . . C16A C 0.3586(5) 0.0528(3) 1.0112(3) 0.0602(16) Uani 1 1 d . . . H16A H 0.3777 0.0345 1.0691 0.072 Uiso 1 1 calc R . . C17A C 0.2548(5) 0.0246(3) 0.9564(3) 0.0456(13) Uani 1 1 d . . . O18A O 0.4836(4) 0.1938(3) 0.8721(3) 0.0957(16) Uani 1 1 d . . . C19A C 0.4408(7) 0.2395(4) 0.8020(5) 0.103(2) Uani 1 1 d . . . H19A H 0.4950 0.2828 0.8016 0.154 Uiso 1 1 calc R . . H19B H 0.3564 0.2559 0.8083 0.154 Uiso 1 1 calc R . . H19C H 0.4407 0.2122 0.7470 0.154 Uiso 1 1 calc R . . O20A O 0.1727(4) -0.0279(2) 0.9826(2) 0.0622(11) Uani 1 1 d . . . C21A C 0.1944(7) -0.0569(4) 1.0722(4) 0.086(2) Uani 1 1 d . . . H21A H 0.2734 -0.0836 1.0802 0.129 Uiso 1 1 calc R . . H21B H 0.1272 -0.0908 1.0822 0.129 Uiso 1 1 calc R . . H21C H 0.1971 -0.0158 1.1140 0.129 Uiso 1 1 calc R . . N1B N 0.0313(4) -0.1768(2) 0.9166(3) 0.0476(11) Uani 1 1 d . . . C2B C -0.0781(5) -0.1718(3) 0.9501(4) 0.0619(16) Uani 1 1 d . . . H2B H -0.1340 -0.1338 0.9285 0.074 Uiso 1 1 calc R . . C3B C -0.1135(5) -0.2191(3) 1.0145(4) 0.0651(17) Uani 1 1 d . . . H3B H -0.1911 -0.2131 1.0360 0.078 Uiso 1 1 calc R . . C4B C -0.0326(5) -0.2755(3) 1.0465(4) 0.0622(16) Uani 1 1 d . . . H4B H -0.0540 -0.3087 1.0901 0.075 Uiso 1 1 calc R . . C5B C 0.0812(5) -0.2819(3) 1.0130(3) 0.0490(13) Uani 1 1 d . . . H5B H 0.1381 -0.3196 1.0339 0.059 Uiso 1 1 calc R . . C6B C 0.1101(4) -0.2320(2) 0.9482(3) 0.0362(11) Uani 1 1 d . . . C7B C 0.2305(4) -0.2365(3) 0.9099(3) 0.0345(11) Uani 1 1 d . . . N8B N 0.3011(4) -0.2981(2) 0.9172(3) 0.0491(11) Uani 1 1 d . . . N9B N 0.3999(4) -0.2781(2) 0.8737(3) 0.0441(10) Uani 1 1 d . . . H9B H 0.4705 -0.3206 0.8608 0.053 Uiso 1 1 d R . . N10B N 0.2772(3) -0.1791(2) 0.8641(2) 0.0341(9) Uani 1 1 d . . . C11B C 0.3853(4) -0.2072(2) 0.8418(3) 0.0344(11) Uani 1 1 d . . . C12B C 0.4734(4) -0.1633(2) 0.7949(3) 0.0344(11) Uani 1 1 d . . . C13B C 0.4367(4) -0.0915(3) 0.7659(3) 0.0393(12) Uani 1 1 d . . . H13B H 0.3575 -0.0736 0.7757 0.047 Uiso 1 1 calc R . . C14B C 0.5154(5) -0.0459(3) 0.7225(3) 0.0411(12) Uani 1 1 d . . . C15B C 0.6342(5) -0.0714(3) 0.7103(3) 0.0534(14) Uani 1 1 d . . . H15B H 0.6886 -0.0407 0.6826 0.064 Uiso 1 1 calc R . . C16B C 0.6719(5) -0.1426(3) 0.7393(4) 0.0557(15) Uani 1 1 d . . . H16B H 0.7528 -0.1593 0.7322 0.067 Uiso 1 1 calc R . . C17B C 0.5915(5) -0.1897(3) 0.7788(3) 0.0470(13) Uani 1 1 d . . . O18B O 0.4652(4) 0.0226(2) 0.6935(3) 0.0657(11) Uani 1 1 d . . . C19B C 0.5334(6) 0.0671(4) 0.6411(5) 0.103(3) Uani 1 1 d . . . H19D H 0.4862 0.1120 0.6236 0.155 Uiso 1 1 calc R . . H19E H 0.5488 0.0394 0.5887 0.155 Uiso 1 1 calc R . . H19F H 0.6125 0.0808 0.6746 0.155 Uiso 1 1 calc R . . O20B O 0.6216(4) -0.2613(2) 0.8068(3) 0.0786(13) Uani 1 1 d . . . C21B C 0.7210(6) -0.2988(4) 0.7715(5) 0.101(3) Uani 1 1 d . . . H21D H 0.8004 -0.2785 0.7979 0.152 Uiso 1 1 calc R . . H21E H 0.7128 -0.2916 0.7078 0.152 Uiso 1 1 calc R . . H21F H 0.7176 -0.3518 0.7846 0.152 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 N1A 0.041(2) 0.039(2) 0.044(3) 0.000(2) -0.013(2) 0.000(2) C2A 0.061(4) 0.052(3) 0.052(4) 0.002(3) -0.010(3) 0.008(3) C3A 0.049(3) 0.070(4) 0.051(3) -0.006(3) -0.020(3) 0.007(3) C4A 0.033(3) 0.058(4) 0.049(3) -0.015(3) -0.005(3) -0.009(3) C5A 0.035(3) 0.042(3) 0.046(3) -0.008(2) 0.003(2) -0.010(2) C6A 0.027(2) 0.038(3) 0.041(3) -0.004(2) 0.003(2) -0.002(2) C7A 0.031(3) 0.038(3) 0.036(3) -0.001(2) 0.006(2) -0.006(2) N8A 0.038(2) 0.042(2) 0.048(3) 0.002(2) -0.006(2) -0.008(2) N9A 0.041(2) 0.041(3) 0.045(3) 0.008(2) -0.002(2) -0.002(2) N10A 0.036(2) 0.034(2) 0.037(2) 0.0005(19) -0.0033(18) -0.0055(19) C11A 0.034(3) 0.036(3) 0.038(3) -0.001(2) 0.001(2) 0.006(2) C12A 0.037(3) 0.045(3) 0.036(3) -0.002(2) -0.005(2) 0.011(2) C13A 0.047(3) 0.049(3) 0.048(3) -0.001(3) -0.007(3) -0.001(3) C14A 0.044(3) 0.066(4) 0.057(4) -0.004(3) -0.010(3) -0.005(3) C15A 0.056(4) 0.084(5) 0.052(4) -0.008(3) -0.013(3) -0.001(3) C16A 0.068(4) 0.073(4) 0.035(3) -0.001(3) -0.012(3) 0.017(3) C17A 0.051(3) 0.048(3) 0.037(3) 0.000(3) -0.001(3) 0.011(3) O18A 0.067(3) 0.113(4) 0.097(3) 0.029(3) -0.030(3) -0.037(3) C19A 0.105(6) 0.106(6) 0.097(6) 0.014(5) 0.007(5) -0.029(5) O20A 0.080(3) 0.064(2) 0.042(2) 0.0083(19) 0.0012(19) -0.004(2) C21A 0.127(6) 0.085(5) 0.045(4) 0.014(3) 0.004(4) -0.002(5) N1B 0.038(2) 0.046(3) 0.062(3) 0.010(2) 0.019(2) 0.006(2) C2B 0.044(3) 0.062(4) 0.084(4) 0.014(3) 0.023(3) 0.012(3) C3B 0.043(3) 0.075(4) 0.084(4) 0.004(4) 0.031(3) 0.001(3) C4B 0.059(4) 0.071(4) 0.062(4) 0.013(3) 0.029(3) -0.012(3) C5B 0.055(3) 0.047(3) 0.046(3) 0.013(3) 0.010(3) -0.004(3) C6B 0.039(3) 0.032(3) 0.037(3) -0.001(2) 0.003(2) -0.007(2) C7B 0.028(3) 0.037(3) 0.038(3) 0.003(2) 0.001(2) 0.000(2) N8B 0.041(3) 0.040(2) 0.068(3) 0.008(2) 0.016(2) 0.006(2) N9B 0.034(2) 0.042(3) 0.059(3) 0.007(2) 0.013(2) 0.008(2) N10B 0.028(2) 0.038(2) 0.036(2) 0.0059(19) 0.0030(17) 0.0005(19) C11B 0.036(3) 0.035(3) 0.032(3) 0.002(2) 0.001(2) 0.002(2) C12B 0.027(3) 0.042(3) 0.033(3) 0.000(2) 0.002(2) 0.006(2) C13B 0.033(3) 0.046(3) 0.039(3) -0.001(2) 0.006(2) 0.002(2) C14B 0.041(3) 0.042(3) 0.040(3) 0.002(2) 0.002(2) -0.003(2) C15B 0.043(3) 0.065(4) 0.053(3) 0.009(3) 0.008(3) -0.011(3) C16B 0.031(3) 0.072(4) 0.066(4) 0.010(3) 0.012(3) 0.006(3) C17B 0.035(3) 0.049(3) 0.056(3) 0.009(3) 0.004(2) 0.008(3) O18B 0.073(3) 0.052(2) 0.076(3) 0.022(2) 0.024(2) 0.008(2) C19B 0.084(5) 0.078(5) 0.150(7) 0.059(5) 0.021(5) -0.013(4) O20B 0.054(2) 0.073(3) 0.118(4) 0.037(3) 0.044(2) 0.034(2) C21B 0.090(5) 0.082(5) 0.143(7) 0.033(5) 0.061(5) 0.053(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 N1A C2A 1.344(6) . ? N1A C6A 1.345(5) . ? C2A C3A 1.378(7) . ? C3A C4A 1.370(7) . ? C4A C5A 1.378(6) . ? C5A C6A 1.391(6) . ? C6A C7A 1.470(6) . ? C7A N8A 1.319(5) . ? C7A N10A 1.359(5) . ? N8A N9A 1.360(5) . ? N9A C11A 1.347(5) . ? N10A C11A 1.337(5) . ? C11A C12A 1.468(6) . ? C12A C17A 1.398(6) . ? C12A C13A 1.402(6) . ? C13A C14A 1.387(7) . ? C14A O18A 1.367(6) . ? C14A C15A 1.377(7) . ? C15A C16A 1.375(7) . ? C16A C17A 1.390(7) . ? C17A O20A 1.367(6) . ? O18A C19A 1.364(7) . ? O20A C21A 1.435(6) . ? N1B C2B 1.329(6) . ? N1B C6B 1.337(6) . ? C2B C3B 1.368(7) . ? C3B C4B 1.368(7) . ? C4B C5B 1.373(7) . ? C5B C6B 1.379(6) . ? C6B C7B 1.472(6) . ? C7B N8B 1.321(5) . ? C7B N10B 1.356(5) . ? N8B N9B 1.353(5) . ? N9B C11B 1.345(5) . ? N10B C11B 1.335(5) . ? C11B C12B 1.464(6) . ? C12B C13B 1.383(6) . ? C12B C17B 1.392(6) . ? C13B C14B 1.383(6) . ? C14B O18B 1.375(6) . ? C14B C15B 1.378(7) . ? C15B C16B 1.378(7) . ? C16B C17B 1.380(7) . ? C17B O20B 1.362(6) . ? O18B C19B 1.382(6) . ? O20B C21B 1.408(6) . ? 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 C2A N1A C6A 116.8(4) . . ? N1A C2A C3A 123.8(5) . . ? C4A C3A C2A 118.7(5) . . ? C3A C4A C5A 119.1(5) . . ? C4A C5A C6A 119.0(5) . . ? N1A C6A C5A 122.6(4) . . ? N1A C6A C7A 115.7(4) . . ? C5A C6A C7A 121.7(4) . . ? N8A C7A N10A 115.2(4) . . ? N8A C7A C6A 122.9(4) . . ? N10A C7A C6A 121.9(4) . . ? C7A N8A N9A 102.4(4) . . ? C11A N9A N8A 110.1(4) . . ? C11A N10A C7A 102.8(4) . . ? N10A C11A N9A 109.5(4) . . ? N10A C11A C12A 123.9(4) . . ? N9A C11A C12A 126.6(4) . . ? C17A C12A C13A 119.3(5) . . ? C17A C12A C11A 123.8(5) . . ? C13A C12A C11A 116.8(4) . . ? C14A C13A C12A 120.5(5) . . ? O18A C14A C15A 116.3(5) . . ? O18A C14A C13A 124.6(5) . . ? C15A C14A C13A 119.0(6) . . ? C16A C15A C14A 121.6(5) . . ? C15A C16A C17A 120.0(5) . . ? O20A C17A C16A 124.3(5) . . ? O20A C17A C12A 116.1(4) . . ? C16A C17A C12A 119.6(5) . . ? C19A O18A C14A 117.9(5) . . ? C17A O20A C21A 118.6(4) . . ? C2B N1B C6B 117.1(4) . . ? N1B C2B C3B 124.0(5) . . ? C4B C3B C2B 118.6(5) . . ? C3B C4B C5B 118.6(5) . . ? C4B C5B C6B 119.3(5) . . ? N1B C6B C5B 122.3(4) . . ? N1B C6B C7B 116.1(4) . . ? C5B C6B C7B 121.5(4) . . ? N8B C7B N10B 114.7(4) . . ? N8B C7B C6B 121.9(4) . . ? N10B C7B C6B 123.4(4) . . ? C7B N8B N9B 102.4(4) . . ? C11B N9B N8B 110.7(4) . . ? C11B N10B C7B 103.4(4) . . ? N10B C11B N9B 108.9(4) . . ? N10B C11B C12B 123.2(4) . . ? N9B C11B C12B 127.8(4) . . ? C13B C12B C17B 118.7(4) . . ? C13B C12B C11B 117.8(4) . . ? C17B C12B C11B 123.6(4) . . ? C12B C13B C14B 121.3(4) . . ? O18B C14B C15B 125.1(4) . . ? O18B C14B C13B 115.4(4) . . ? C15B C14B C13B 119.5(5) . . ? C16B C15B C14B 119.6(5) . . ? C15B C16B C17B 121.0(5) . . ? O20B C17B C16B 124.0(5) . . ? O20B C17B C12B 116.3(4) . . ? C16B C17B C12B 119.7(5) . . ? C14B O18B C19B 118.2(4) . . ? C17B O20B C21B 118.8(4) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 22.19 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.250 _refine_diff_density_min -0.368 _refine_diff_density_rms 0.085 data_tia1 _database_code_CSD 171757 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H18 N8 O2' _chemical_formula_weight 426.44 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 P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.235(3) _cell_length_b 11.636(3) _cell_length_c 10.096(3) _cell_angle_alpha 90.00 _cell_angle_beta 106.44(2) _cell_angle_gamma 90.00 _cell_volume 1040.5(5) _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 Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.76 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.361 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 444 _exptl_absorpt_coefficient_mu 0.093 _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 'Siemens P4' _diffrn_measurement_method XSCANS _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1853 _diffrn_reflns_av_R_equivalents 0.0528 _diffrn_reflns_av_sigmaI/netI 0.1285 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 22.50 _reflns_number_total 1359 _reflns_number_gt 769 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.0401P)^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 1359 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1399 _refine_ls_R_factor_gt 0.0609 _refine_ls_wR_factor_ref 0.1235 _refine_ls_wR_factor_gt 0.0992 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 1.005 _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 -0.2947(5) 0.9709(4) -0.3154(4) 0.0395(13) Uani 1 1 d . . . C2 C -0.3419(7) 1.0630(5) -0.3973(5) 0.0511(18) Uani 1 1 d . . . H2 H -0.3186 1.0612 -0.4972 0.061 Uiso 1 1 d R . . C3 C -0.4262(6) 1.1516(4) -0.3665(5) 0.0399(14) Uani 1 1 d . . . H3 H -0.4476 1.2183 -0.4381 0.048 Uiso 1 1 d R . . C4 C -0.4620(6) 1.1470(5) -0.2437(5) 0.0377(14) Uani 1 1 d . . . H4 H -0.5113 1.2170 -0.2169 0.045 Uiso 1 1 d R . . C5 C -0.4169(5) 1.0535(4) -0.1579(5) 0.0281(13) Uani 1 1 d . . . H5 H -0.4254 1.0396 -0.0564 0.034 Uiso 1 1 d R . . C6 C -0.3318(5) 0.9678(4) -0.1971(4) 0.0228(12) Uani 1 1 d . . . C7 C -0.2719(5) 0.8688(4) -0.1058(4) 0.0233(12) Uani 1 1 d . . . N8 N -0.2796(4) 0.8651(3) 0.0244(4) 0.0231(10) Uani 1 1 d . . . N9 N -0.2032(4) 0.7658(3) 0.0724(3) 0.0230(10) Uani 1 1 d . . . H9 H -0.1888 0.7422 0.1830 0.028 Uiso 1 1 d R . . C10 C -0.1564(5) 0.7149(4) -0.0278(4) 0.0211(12) Uani 1 1 d . . . N11 N -0.2004(4) 0.7785(3) -0.1443(3) 0.0202(10) Uani 1 1 d . . . C12 C -0.0747(5) 0.6055(4) -0.0131(4) 0.0215(12) Uani 1 1 d . . . C13 C -0.0998(5) 0.5318(4) -0.1266(5) 0.0204(12) Uani 1 1 d . . . H13 H -0.1862 0.5590 -0.2264 0.025 Uiso 1 1 d R . . C14 C 0.0263(5) 0.5740(4) 0.1142(4) 0.0229(12) Uani 1 1 d . . . O15 O 0.0482(4) 0.6536(3) 0.2173(3) 0.0319(9) Uani 1 1 d . . . C16 C 0.1358(6) 0.6192(5) 0.3532(4) 0.0434(16) Uani 1 1 d . . . H16A H 0.2498 0.6020 0.3457 0.052 Uiso 1 1 d R . . H16B H 0.0681 0.5418 0.3802 0.052 Uiso 1 1 d R . . H16C H 0.1396 0.7016 0.4086 0.052 Uiso 1 1 d 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 0.054(3) 0.037(3) 0.036(3) 0.010(2) 0.026(2) 0.013(3) C2 0.071(5) 0.049(4) 0.041(3) 0.025(3) 0.028(3) 0.026(4) C3 0.049(4) 0.032(3) 0.038(3) 0.014(3) 0.011(3) 0.016(3) C4 0.044(4) 0.029(3) 0.040(3) 0.002(3) 0.011(3) 0.006(3) C5 0.035(3) 0.025(3) 0.026(3) 0.000(2) 0.010(3) 0.008(3) C6 0.022(3) 0.024(3) 0.020(3) 0.001(2) 0.003(2) 0.005(3) C7 0.027(3) 0.026(3) 0.018(3) 0.000(2) 0.007(2) -0.002(3) N8 0.027(3) 0.020(2) 0.023(2) 0.000(2) 0.0074(19) 0.003(2) N9 0.031(3) 0.021(2) 0.018(2) 0.0015(19) 0.0091(19) 0.007(2) C10 0.024(3) 0.020(3) 0.021(3) -0.001(2) 0.008(2) -0.001(3) N11 0.031(3) 0.016(2) 0.017(2) -0.002(2) 0.0116(19) 0.000(2) C12 0.025(3) 0.021(3) 0.022(3) -0.001(2) 0.012(2) 0.000(3) C13 0.025(3) 0.018(3) 0.017(3) 0.006(2) 0.003(2) 0.004(3) C14 0.030(3) 0.022(3) 0.018(3) -0.003(2) 0.008(2) -0.005(3) O15 0.042(2) 0.025(2) 0.0233(18) -0.0053(17) 0.0007(17) 0.0124(18) C16 0.053(4) 0.042(4) 0.026(3) -0.010(3) -0.005(3) 0.015(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C6 1.333(5) . ? N1 C2 1.348(6) . ? C2 C3 1.380(7) . ? C3 C4 1.372(7) . ? C4 C5 1.380(6) . ? C5 C6 1.395(6) . ? C6 C7 1.480(6) . ? C7 N8 1.338(5) . ? C7 N11 1.356(5) . ? N8 N9 1.369(5) . ? N9 C10 1.344(5) . ? C10 N11 1.350(5) . ? C10 C12 1.466(6) . ? C12 C13 1.397(6) . ? C12 C14 1.406(6) . ? C13 C14 1.394(6) 3_565 ? C14 O15 1.365(5) . ? C14 C13 1.394(6) 3_565 ? O15 C16 1.439(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 116.8(5) . . ? N1 C2 C3 124.1(5) . . ? C4 C3 C2 118.0(5) . . ? C3 C4 C5 119.4(5) . . ? C4 C5 C6 118.7(4) . . ? N1 C6 C5 122.9(4) . . ? N1 C6 C7 115.7(4) . . ? C5 C6 C7 121.4(4) . . ? N8 C7 N11 115.0(4) . . ? N8 C7 C6 121.5(4) . . ? N11 C7 C6 123.5(4) . . ? C7 N8 N9 102.1(3) . . ? C10 N9 N8 110.4(3) . . ? N9 C10 N11 109.4(4) . . ? N9 C10 C12 124.9(4) . . ? N11 C10 C12 125.7(4) . . ? C10 N11 C7 103.1(3) . . ? C13 C12 C14 120.2(4) . . ? C13 C12 C10 119.2(4) . . ? C14 C12 C10 120.6(4) . . ? C14 C13 C12 120.3(4) 3_565 . ? O15 C14 C13 124.6(4) . 3_565 ? O15 C14 C12 115.9(4) . . ? C13 C14 C12 119.5(4) 3_565 . ? C14 O15 C16 117.4(4) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 22.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.244 _refine_diff_density_min -0.256 _refine_diff_density_rms 0.059