# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) 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 'Claudio Pettinari' _publ_contact_author_email claudio.pettinari@unicam.it loop_ _publ_author_name 'C.Di Nicola' F.Garau F.Marchetti M.Monari L.Pandolfo ; C.Pettinari ; A.Venzo data_L3 _database_code_depnum_ccdc_archive 'CCDC 790411' #TrackingRef '- threecomp.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H27 N21' _chemical_formula_weight 717.76 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.8379(5) _cell_length_b 11.6404(7) _cell_length_c 18.3088(11) _cell_angle_alpha 80.857(1) _cell_angle_beta 85.384(1) _cell_angle_gamma 67.977(1) _cell_volume 1723.48(18) _cell_formula_units_Z 2 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 4109 _cell_measurement_theta_min 2.17 _cell_measurement_theta_max 24.76 _exptl_crystal_description parallelepiped _exptl_crystal_colour white _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.383 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.969 _exptl_absorpt_correction_T_max 0.985 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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 'Bruker SMART Apex II CCD' _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 19697 _diffrn_reflns_av_R_equivalents 0.0271 _diffrn_reflns_av_sigmaI/netI 0.0390 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 27.42 _reflns_number_total 7708 _reflns_number_gt 4197 _reflns_threshold_expression >2\s(I) _computing_data_collection SMART _computing_cell_refinement SMART _computing_data_reduction SAINT+ _computing_structure_solution 'SIR-97 (Giacovazzo, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL99 (Keller 1999)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1691P)^2^+0.2492P] 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 7708 _refine_ls_number_parameters 487 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1311 _refine_ls_R_factor_gt 0.0792 _refine_ls_wR_factor_ref 0.2910 _refine_ls_wR_factor_gt 0.2510 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N2 N 0.1167(3) 0.9509(2) 0.31319(12) 0.0538(6) Uani 1 1 d . . . N3 N 0.2006(3) 0.9563(2) 0.18728(13) 0.0590(6) Uani 1 1 d . . . N1 N 0.2927(3) 0.7673(2) 0.26840(13) 0.0613(6) Uani 1 1 d . . . C3 C 0.1207(3) 1.0082(3) 0.24515(15) 0.0546(7) Uani 1 1 d . . . C1 C 0.2058(3) 0.8293(3) 0.32157(15) 0.0528(7) Uani 1 1 d . . . C2 C 0.2834(4) 0.8353(3) 0.20271(15) 0.0572(7) Uani 1 1 d . . . C6 C 0.2033(3) 0.7537(3) 0.39855(15) 0.0556(7) Uani 1 1 d . . . C5 C 0.0147(4) 1.1487(3) 0.23200(17) 0.0642(8) Uani 1 1 d . . . C4 C 0.3816(4) 0.7634(3) 0.13962(16) 0.0662(8) Uani 1 1 d . . . C28 C 0.3215(4) 0.8842(4) 0.44309(18) 0.0810(11) Uani 1 1 d . . . H28 H 0.3855 0.8912 0.4010 0.097 Uiso 1 1 calc R . . C30 C 0.2098(5) 0.9021(4) 0.5550(2) 0.0854(11) Uani 1 1 d . . . H30 H 0.1851 0.9255 0.6021 0.102 Uiso 1 1 calc R . . C27 C -0.1263(5) 0.6587(4) 0.4551(2) 0.0839(11) Uani 1 1 d . . . H27 H -0.1797 0.6135 0.4858 0.101 Uiso 1 1 calc R . . C25 C -0.0769(4) 0.7834(3) 0.3626(2) 0.0771(10) Uani 1 1 d . . . H25 H -0.0852 0.8381 0.3189 0.092 Uiso 1 1 calc R . . C20 C 0.0499(9) 1.3700(5) 0.3291(3) 0.128(2) Uani 1 1 d . . . H20 H 0.0169 1.4507 0.3410 0.154 Uiso 1 1 calc R . . C19 C -0.0298(6) 1.3345(3) 0.2864(2) 0.0936(12) Uani 1 1 d . . . H19 H -0.1249 1.3846 0.2614 0.112 Uiso 1 1 calc R . . C24 C -0.3480(5) 1.0968(5) 0.2308(2) 0.0961(12) Uani 1 1 d . . . H24 H -0.4074 1.0469 0.2271 0.115 Uiso 1 1 calc R . . C26 C -0.1888(5) 0.7382(4) 0.3923(3) 0.1009(14) Uani 1 1 d . . . H26 H -0.2915 0.7573 0.3737 0.121 Uiso 1 1 calc R . . C31 C 0.4917(4) 0.6114(4) 0.4173(2) 0.0866(11) Uani 1 1 d . . . H31 H 0.5311 0.6663 0.4337 0.104 Uiso 1 1 calc R . . C22 C -0.2930(6) 1.2597(4) 0.2403(3) 0.1030(14) Uani 1 1 d . . . H22 H -0.3010 1.3408 0.2433 0.124 Uiso 1 1 calc R . . C8 C 0.2668(6) 0.4951(4) 0.1475(3) 0.0989(12) Uani 1 1 d . . . H8 H 0.2230 0.4348 0.1661 0.119 Uiso 1 1 calc R . . C33 C 0.4733(6) 0.4516(4) 0.3793(3) 0.1037(14) Uani 1 1 d . . . H33 H 0.5029 0.3725 0.3653 0.124 Uiso 1 1 calc R . . C9 C 0.3398(14) 0.5125(6) 0.0796(4) 0.209(4) Uani 1 1 d . . . H9 H 0.3565 0.4603 0.0437 0.251 Uiso 1 1 calc R . . C29 C 0.3130(5) 0.9316(4) 0.5048(2) 0.0965(12) Uani 1 1 d . . . H29 H 0.3719 0.9799 0.5125 0.116 Uiso 1 1 calc R . . C23 C -0.4171(5) 1.2211(5) 0.2360(3) 0.1114(15) Uani 1 1 d . . . H23 H -0.5280 1.2697 0.2365 0.134 Uiso 1 1 calc R . . C32 C 0.5802(5) 0.4956(5) 0.4023(3) 0.1079(15) Uani 1 1 d . . . H32 H 0.6924 0.4540 0.4067 0.129 Uiso 1 1 calc R . . C18 C 0.1745(11) 1.2663(6) 0.0709(3) 0.151(3) Uani 1 1 d . . . H18 H 0.2535 1.2914 0.0441 0.181 Uiso 1 1 calc R . . C15 C 0.2300(7) 0.9512(4) -0.0274(3) 0.1090(15) Uani 1 1 d . . . H15 H 0.1485 1.0012 -0.0603 0.131 Uiso 1 1 calc R . . C11 C 0.8093(9) 0.6210(10) 0.1638(6) 0.224(6) Uani 1 1 d . . . H11 H 0.9133 0.5596 0.1630 0.269 Uiso 1 1 calc R . . C12 C 0.7648(7) 0.7440(11) 0.1873(4) 0.194(5) Uani 1 1 d . . . H12 H 0.8384 0.7750 0.2023 0.233 Uiso 1 1 calc R . . C21 C 0.1873(8) 1.2743(6) 0.3541(3) 0.1200(19) Uani 1 1 d . . . H21 H 0.2642 1.2777 0.3846 0.144 Uiso 1 1 calc R . . C16 C -0.0450(7) 1.2286(4) 0.0963(2) 0.1072(15) Uani 1 1 d . . . H16 H -0.1441 1.2193 0.0930 0.129 Uiso 1 1 calc R . . C17 C 0.0418(11) 1.2671(6) 0.0410(3) 0.148(3) Uani 1 1 d . . . H17 H 0.0143 1.2899 -0.0087 0.177 Uiso 1 1 calc R . . C10 C 0.6757(7) 0.6142(6) 0.1445(3) 0.158(3) Uani 1 1 d . . . H10 H 0.6658 0.5485 0.1248 0.189 Uiso 1 1 calc R . . N7 N 0.3835(12) 0.6097(5) 0.0703(3) 0.234(4) Uani 1 1 d . . . C14 C 0.3853(10) 0.9222(12) -0.0392(3) 0.259(7) Uani 1 1 d . . . H14 H 0.4346 0.9451 -0.0829 0.311 Uiso 1 1 calc R . . C13 C 0.4628(7) 0.8546(10) 0.0214(3) 0.229(5) Uani 1 1 d . . . H13 H 0.5751 0.8221 0.0278 0.275 Uiso 1 1 calc R . . N20 N 0.0489(3) 0.7354(2) 0.40751(13) 0.0600(6) Uani 1 1 d . . . N16 N 0.2179(3) 0.8240(2) 0.45452(13) 0.0589(6) Uani 1 1 d . . . N18 N 0.3351(3) 0.6331(2) 0.40417(13) 0.0591(6) Uani 1 1 d . . . N10 N -0.1532(3) 1.1568(2) 0.23927(15) 0.0680(7) Uani 1 1 d . . . N8 N 0.3545(3) 0.8426(2) 0.06916(13) 0.0666(7) Uani 1 1 d . . . N12 N 0.0412(4) 1.2063(2) 0.15731(16) 0.0775(9) Uani 1 1 d . . . N14 N 0.0516(4) 1.2120(3) 0.28541(17) 0.0773(8) Uani 1 1 d . . . N11 N -0.1865(4) 1.0550(3) 0.23151(16) 0.0771(8) Uani 1 1 d . . . N17 N 0.1482(4) 0.8308(3) 0.52329(17) 0.0910(9) Uani 1 1 d . . . N6 N 0.3366(4) 0.6566(3) 0.13343(16) 0.0876(10) Uani 1 1 d . . . N21 N 0.0227(4) 0.6553(3) 0.46574(16) 0.0878(9) Uani 1 1 d . . . N19 N 0.3184(4) 0.5356(3) 0.37907(19) 0.0907(9) Uani 1 1 d . . . N13 N 0.1825(5) 1.2259(4) 0.1431(2) 0.1131(13) Uani 1 1 d . . . N4 N 0.5527(4) 0.7214(4) 0.15845(16) 0.0969(12) Uani 1 1 d . . . N15 N 0.1904(6) 1.1716(4) 0.3255(2) 0.1215(14) Uani 1 1 d . . . C7 C 0.2756(5) 0.5877(4) 0.1795(2) 0.0925(12) Uani 1 1 d . . . H7 H 0.2426 0.6009 0.2280 0.111 Uiso 1 1 calc R . . N5 N 0.6024(5) 0.8059(5) 0.1841(2) 0.1224(15) Uani 1 1 d . . . N9 N 0.2074(4) 0.8969(4) 0.04011(19) 0.0972(10) 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 N2 0.0580(13) 0.0553(14) 0.0540(13) -0.0162(10) 0.0139(10) -0.0274(11) N3 0.0665(15) 0.0549(14) 0.0558(14) -0.0144(11) 0.0140(11) -0.0232(12) N1 0.0617(14) 0.0621(14) 0.0511(13) -0.0110(11) 0.0136(11) -0.0144(12) C3 0.0608(16) 0.0573(16) 0.0540(16) -0.0186(13) 0.0151(12) -0.0302(13) C1 0.0497(15) 0.0592(17) 0.0545(15) -0.0147(12) 0.0112(12) -0.0255(13) C2 0.0583(16) 0.0593(17) 0.0520(16) -0.0141(13) 0.0095(12) -0.0191(14) C6 0.0516(15) 0.0697(18) 0.0496(15) -0.0126(13) 0.0093(12) -0.0271(14) C5 0.086(2) 0.0527(16) 0.0613(17) -0.0189(13) 0.0238(15) -0.0353(15) C4 0.070(2) 0.0604(18) 0.0543(17) -0.0128(13) 0.0156(14) -0.0094(15) C28 0.084(2) 0.137(3) 0.0615(19) -0.035(2) 0.0207(16) -0.082(2) C30 0.108(3) 0.090(2) 0.067(2) -0.0320(19) 0.007(2) -0.039(2) C27 0.084(2) 0.112(3) 0.078(2) -0.009(2) 0.0109(18) -0.065(2) C25 0.081(2) 0.090(2) 0.074(2) 0.0139(18) -0.0224(18) -0.053(2) C20 0.198(6) 0.098(3) 0.126(4) -0.070(3) 0.076(4) -0.092(4) C19 0.138(4) 0.0500(19) 0.095(3) -0.0340(18) 0.020(2) -0.031(2) C24 0.071(2) 0.118(4) 0.095(3) -0.003(2) 0.003(2) -0.035(2) C26 0.084(3) 0.113(3) 0.124(3) 0.018(3) -0.030(2) -0.064(2) C31 0.055(2) 0.089(3) 0.112(3) -0.008(2) -0.0019(19) -0.0235(19) C22 0.096(3) 0.062(2) 0.122(3) -0.009(2) 0.023(3) -0.003(2) C8 0.124(3) 0.087(3) 0.088(3) -0.019(2) 0.001(2) -0.040(3) C33 0.111(3) 0.070(2) 0.112(3) -0.025(2) 0.031(3) -0.015(2) C9 0.448(14) 0.100(4) 0.118(5) -0.049(3) 0.036(6) -0.137(7) C29 0.103(3) 0.126(3) 0.091(3) -0.033(2) -0.002(2) -0.070(3) C23 0.068(3) 0.110(4) 0.123(4) 0.000(3) 0.009(2) -0.004(3) C32 0.065(2) 0.099(3) 0.136(4) 0.000(3) 0.009(2) -0.013(2) C18 0.261(8) 0.130(4) 0.109(4) -0.048(3) 0.108(5) -0.137(5) C15 0.144(4) 0.101(3) 0.082(3) 0.006(2) -0.043(3) -0.045(3) C11 0.086(5) 0.253(11) 0.196(8) 0.086(7) 0.031(5) 0.040(6) C12 0.069(4) 0.359(14) 0.111(4) 0.047(6) -0.026(3) -0.056(6) C21 0.164(5) 0.137(5) 0.115(4) -0.068(3) 0.050(4) -0.110(4) C16 0.180(5) 0.089(3) 0.059(2) -0.007(2) 0.007(3) -0.060(3) C17 0.269(9) 0.114(4) 0.083(3) -0.015(3) 0.050(4) -0.106(5) C10 0.094(4) 0.152(5) 0.125(4) 0.025(4) 0.029(3) 0.047(4) N7 0.516(13) 0.121(4) 0.103(3) -0.064(3) 0.108(5) -0.165(6) C14 0.174(7) 0.553(19) 0.091(4) 0.099(7) -0.033(4) -0.231(10) C13 0.093(4) 0.491(15) 0.061(3) 0.065(5) 0.003(2) -0.101(6) N20 0.0585(14) 0.0778(16) 0.0517(13) -0.0097(12) 0.0082(11) -0.0358(13) N16 0.0553(14) 0.0737(16) 0.0517(13) -0.0159(11) 0.0085(10) -0.0274(12) N18 0.0572(15) 0.0618(15) 0.0578(14) -0.0078(11) 0.0058(11) -0.0229(12) N10 0.0726(17) 0.0497(14) 0.0742(17) -0.0068(12) 0.0159(13) -0.0184(13) N8 0.0675(16) 0.0724(16) 0.0517(14) -0.0107(12) 0.0092(12) -0.0178(13) N12 0.114(2) 0.0526(14) 0.0729(19) -0.0174(13) 0.0339(17) -0.0425(15) N14 0.101(2) 0.0675(17) 0.0780(18) -0.0332(14) 0.0298(17) -0.0446(16) N11 0.0761(19) 0.0696(17) 0.086(2) -0.0110(14) 0.0040(14) -0.0284(14) N17 0.111(2) 0.090(2) 0.0742(19) -0.0247(16) 0.0172(17) -0.0375(19) N6 0.126(3) 0.0593(16) 0.0630(17) -0.0216(13) 0.0248(17) -0.0182(17) N21 0.087(2) 0.118(3) 0.0706(18) 0.0061(17) 0.0041(15) -0.0601(19) N19 0.096(2) 0.077(2) 0.105(2) -0.0343(17) 0.0134(18) -0.0332(18) N13 0.156(3) 0.110(3) 0.106(3) -0.037(2) 0.061(2) -0.091(3) N4 0.070(2) 0.116(3) 0.0587(17) -0.0010(17) 0.0194(14) 0.0094(19) N15 0.153(4) 0.130(3) 0.126(3) -0.056(3) 0.036(3) -0.095(3) C7 0.102(3) 0.129(3) 0.072(2) -0.034(2) 0.020(2) -0.067(3) N5 0.076(2) 0.198(5) 0.094(3) -0.030(3) -0.0016(19) -0.049(3) N9 0.089(2) 0.114(3) 0.083(2) -0.025(2) -0.0101(18) -0.025(2) _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 N2 C3 1.321(4) . ? N2 C1 1.328(4) . ? N3 C2 1.316(4) . ? N3 C3 1.322(3) . ? N1 C1 1.321(3) . ? N1 C2 1.321(4) . ? C3 C5 1.541(4) . ? C1 C6 1.542(4) . ? C2 C4 1.546(4) . ? C6 N18 1.444(4) . ? C6 N20 1.450(3) . ? C6 N16 1.450(4) . ? C5 N14 1.437(4) . ? C5 N10 1.448(4) . ? C5 N12 1.466(4) . ? C4 N8 1.441(4) . ? C4 N4 1.456(5) . ? C4 N6 1.462(5) . ? C28 C29 1.318(5) . ? C28 N16 1.334(4) . ? C30 C29 1.340(5) . ? C30 N17 1.366(5) . ? C27 N21 1.332(4) . ? C27 C26 1.365(5) . ? C25 N20 1.326(4) . ? C25 C26 1.328(5) . ? C20 C19 1.299(7) . ? C20 C21 1.356(8) . ? C19 N14 1.338(4) . ? C24 N11 1.325(5) . ? C24 C23 1.359(7) . ? C31 C32 1.341(6) . ? C31 N18 1.345(4) . ? C22 C23 1.343(7) . ? C22 N10 1.362(5) . ? C8 C7 1.336(6) . ? C8 C9 1.375(8) . ? C33 N19 1.351(5) . ? C33 C32 1.352(7) . ? C9 N7 1.309(8) . ? C18 N13 1.330(7) . ? C18 C17 1.331(10) . ? C15 C14 1.293(8) . ? C15 N9 1.333(5) . ? C11 C10 1.292(13) . ? C11 C12 1.462(15) . ? C12 N5 1.345(7) . ? C21 N15 1.370(6) . ? C16 N12 1.338(6) . ? C16 C17 1.344(7) . ? C10 N4 1.358(6) . ? N7 N6 1.326(5) . ? C14 C13 1.327(9) . ? C13 N8 1.276(5) . ? N20 N21 1.366(4) . ? N16 N17 1.357(4) . ? N18 N19 1.350(4) . ? N10 N11 1.354(4) . ? N8 N9 1.327(4) . ? N12 N13 1.350(5) . ? N14 N15 1.367(5) . ? N6 C7 1.297(5) . ? N4 N5 1.373(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 C3 N2 C1 113.9(2) . . ? C2 N3 C3 113.5(2) . . ? C1 N1 C2 114.9(2) . . ? N2 C3 N3 126.7(3) . . ? N2 C3 C5 115.9(2) . . ? N3 C3 C5 117.3(2) . . ? N1 C1 N2 125.0(3) . . ? N1 C1 C6 117.4(2) . . ? N2 C1 C6 117.6(2) . . ? N3 C2 N1 126.0(3) . . ? N3 C2 C4 118.6(2) . . ? N1 C2 C4 115.4(2) . . ? N18 C6 N20 109.1(2) . . ? N18 C6 N16 110.1(2) . . ? N20 C6 N16 110.5(2) . . ? N18 C6 C1 110.6(2) . . ? N20 C6 C1 107.6(2) . . ? N16 C6 C1 108.9(2) . . ? N14 C5 N10 111.6(3) . . ? N14 C5 N12 109.3(2) . . ? N10 C5 N12 108.4(3) . . ? N14 C5 C3 109.8(3) . . ? N10 C5 C3 106.1(2) . . ? N12 C5 C3 111.6(2) . . ? N8 C4 N4 109.6(3) . . ? N8 C4 N6 107.9(3) . . ? N4 C4 N6 110.6(3) . . ? N8 C4 C2 111.6(2) . . ? N4 C4 C2 105.9(3) . . ? N6 C4 C2 111.3(3) . . ? C29 C28 N16 104.6(3) . . ? C29 C30 N17 106.3(3) . . ? N21 C27 C26 109.9(3) . . ? N20 C25 C26 106.6(3) . . ? C19 C20 C21 111.4(4) . . ? C20 C19 N14 106.6(5) . . ? N11 C24 C23 112.3(4) . . ? C25 C26 C27 107.9(3) . . ? C32 C31 N18 107.0(4) . . ? C23 C22 N10 106.5(4) . . ? C7 C8 C9 101.5(4) . . ? N19 C33 C32 112.3(4) . . ? N7 C9 C8 113.4(5) . . ? C28 C29 C30 112.3(3) . . ? C22 C23 C24 106.2(4) . . ? C31 C32 C33 106.1(4) . . ? N13 C18 C17 112.9(5) . . ? C14 C15 N9 108.0(4) . . ? C10 C11 C12 106.6(6) . . ? N5 C12 C11 110.3(8) . . ? C20 C21 N15 106.4(5) . . ? N12 C16 C17 105.6(6) . . ? C18 C17 C16 106.7(5) . . ? C11 C10 N4 106.8(8) . . ? C9 N7 N6 103.3(5) . . ? C15 C14 C13 108.8(5) . . ? N8 C13 C14 107.2(5) . . ? C25 N20 N21 111.5(2) . . ? C25 N20 C6 128.0(3) . . ? N21 N20 C6 120.5(2) . . ? C28 N16 N17 111.6(3) . . ? C28 N16 C6 119.5(2) . . ? N17 N16 C6 128.7(2) . . ? C31 N18 N19 112.1(3) . . ? C31 N18 C6 125.6(3) . . ? N19 N18 C6 120.7(3) . . ? N11 N10 C22 110.9(3) . . ? N11 N10 C5 118.7(2) . . ? C22 N10 C5 129.3(3) . . ? C13 N8 N9 110.1(3) . . ? C13 N8 C4 127.0(4) . . ? N9 N8 C4 122.0(3) . . ? C16 N12 N13 112.6(3) . . ? C16 N12 C5 129.3(3) . . ? N13 N12 C5 117.5(3) . . ? C19 N14 N15 110.2(3) . . ? C19 N14 C5 120.6(4) . . ? N15 N14 C5 127.0(3) . . ? C24 N11 N10 104.0(3) . . ? N16 N17 C30 105.2(3) . . ? C7 N6 N7 111.2(4) . . ? C7 N6 C4 133.8(3) . . ? N7 N6 C4 114.5(4) . . ? C27 N21 N20 104.1(3) . . ? N18 N19 C33 102.6(3) . . ? C18 N13 N12 102.2(5) . . ? C10 N4 N5 114.6(5) . . ? C10 N4 C4 127.7(5) . . ? N5 N4 C4 117.1(3) . . ? N14 N15 C21 105.3(5) . . ? N6 C7 C8 110.4(4) . . ? C12 N5 N4 101.6(7) . . ? N8 N9 C15 105.7(4) . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 27.42 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.559 _refine_diff_density_min -0.364 _refine_diff_density_rms 0.051 #===END # Attachment '- comp7-Zn.cif' data_comp-7 _database_code_depnum_ccdc_archive 'CCDC 790412' #TrackingRef '- comp7-Zn.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H20 F6 N12 O6 S2 Zn' _chemical_formula_weight 791.99 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 '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 7.9565(16) _cell_length_b 9.891(2) _cell_length_c 10.939(2) _cell_angle_alpha 68.19(3) _cell_angle_beta 83.31(3) _cell_angle_gamma 82.96(3) _cell_volume 790.9(3) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour white _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.663 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 400 _exptl_absorpt_coefficient_mu 1.002 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.920 _exptl_absorpt_correction_T_max 0.938 _exptl_absorpt_process_details SADABS _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 'Bruker SMART Apex II CCD' _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 3488 _diffrn_reflns_av_R_equivalents 0.2370 _diffrn_reflns_av_sigmaI/netI 0.3756 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.40 _diffrn_reflns_theta_max 21.86 _reflns_number_total 1764 _reflns_number_gt 631 _reflns_threshold_expression >2\s(I) _computing_data_collection SMART _computing_cell_refinement SMART _computing_data_reduction SAINT+ _computing_structure_solution 'SIR-97 (Giacovazzo, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL99 (Keller 1999)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1859P)^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 1764 _refine_ls_number_parameters 217 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.2976 _refine_ls_R_factor_gt 0.1524 _refine_ls_wR_factor_ref 0.3865 _refine_ls_wR_factor_gt 0.3195 _refine_ls_goodness_of_fit_ref 0.984 _refine_ls_restrained_S_all 0.984 _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 Zn Zn 0.5000 0.0000 1.0000 0.0566(17) Uani 1 2 d S . . S S 0.7499(9) 0.7011(8) 0.6547(7) 0.074(2) Uani 1 1 d . . . O1 O 0.841(3) 0.680(2) 0.7657(18) 0.121(7) Uani 1 1 d . . . N5 N 0.649(3) 0.072(2) 0.820(2) 0.080(7) Uani 1 1 d . . . C6 C 0.235(3) -0.068(3) 0.711(3) 0.069(8) Uani 1 1 d . . . H4 H 0.2005 -0.0278 0.6257 0.083 Uiso 1 1 calc R . . N2 N 0.309(2) 0.225(2) 0.7819(18) 0.060(4) Uani 1 1 d . . . N6 N 0.563(3) 0.125(2) 0.6999(19) 0.060(4) Uani 1 1 d D . . O2 O 0.625(3) 0.820(2) 0.622(3) 0.160(10) Uani 1 1 d . . . C8 C 0.832(3) 0.136(3) 0.647(4) 0.082(9) Uani 1 1 d . . . H22 H 0.9367 0.1538 0.5992 0.098 Uiso 1 1 calc R . . C11 C 0.388(3) 0.132(3) 0.713(3) 0.074(8) Uani 1 1 d D . . H11 H 0.3521 0.1768 0.6228 0.089 Uiso 1 1 calc R . . N1 N 0.334(2) 0.189(3) 0.9154(18) 0.078(7) Uani 1 1 d . . . N3 N 0.360(3) -0.089(2) 0.889(2) 0.071(6) Uani 1 1 d . . . N4 N 0.327(2) -0.007(2) 0.7641(19) 0.052(5) Uani 1 1 d D . . C1 C 0.256(5) 0.275(3) 0.966(3) 0.114(12) Uani 1 1 d . . . H3 H 0.2598 0.2765 1.0502 0.137 Uiso 1 1 calc R . . C3 C 0.189(3) 0.342(3) 0.748(3) 0.080(9) Uani 1 1 d . . . H1 H 0.1449 0.3859 0.6658 0.096 Uiso 1 1 calc R . . C5 C 0.202(4) -0.192(4) 0.797(3) 0.097(10) Uani 1 1 d . . . H5 H 0.1402 -0.2602 0.7848 0.116 Uiso 1 1 calc R . . C4 C 0.274(3) -0.207(3) 0.909(3) 0.086(9) Uani 1 1 d . . . H6 H 0.2657 -0.2867 0.9884 0.103 Uiso 1 1 calc R . . C7 C 0.801(5) 0.071(3) 0.781(3) 0.091(10) Uani 1 1 d . . . H8 H 0.8867 0.0303 0.8377 0.110 Uiso 1 1 calc R . . C9 C 0.673(4) 0.171(2) 0.597(3) 0.084(10) Uani 1 1 d . . . H7 H 0.6491 0.2164 0.5088 0.101 Uiso 1 1 calc R . . C10 C 0.639(4) 0.549(4) 0.704(4) 0.104(12) Uani 1 1 d . . . F1 F 0.538(3) 0.538(3) 0.805(4) 0.218(16) Uani 1 1 d . . . F2 F 0.726(3) 0.425(2) 0.740(2) 0.182(10) Uani 1 1 d . . . F3 F 0.550(3) 0.539(2) 0.614(3) 0.206(14) Uani 1 1 d . . . O3 O 0.841(3) 0.692(3) 0.545(2) 0.147(10) Uani 1 1 d . . . C2 C 0.149(3) 0.379(3) 0.848(3) 0.076(8) Uani 1 1 d . . . H10 H 0.0693 0.4556 0.8509 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 Zn 0.051(3) 0.055(3) 0.058(3) -0.015(2) -0.022(2) 0.014(2) S 0.077(5) 0.085(6) 0.066(5) -0.026(4) -0.014(5) -0.022(5) O1 0.141(18) 0.16(2) 0.097(15) -0.076(14) -0.037(14) -0.009(15) N5 0.034(13) 0.091(17) 0.12(2) -0.052(15) -0.007(14) 0.024(12) C6 0.065(17) 0.045(17) 0.12(2) -0.043(18) -0.041(17) 0.003(14) N2 0.058(10) 0.060(9) 0.050(9) -0.014(8) -0.001(8) 0.013(8) N6 0.058(10) 0.060(9) 0.050(9) -0.014(8) -0.001(8) 0.013(8) O2 0.16(2) 0.072(14) 0.21(2) -0.021(15) -0.072(19) 0.075(16) C8 0.034(18) 0.08(2) 0.15(3) -0.07(2) -0.003(19) -0.013(16) C11 0.048(17) 0.08(2) 0.10(2) -0.043(19) -0.030(16) 0.002(15) N1 0.079(15) 0.122(19) 0.047(14) -0.057(14) 0.028(11) -0.012(14) N3 0.071(14) 0.054(14) 0.082(17) -0.026(13) -0.016(13) 0.033(13) N4 0.059(13) 0.047(13) 0.053(14) -0.025(12) 0.000(11) -0.002(11) C1 0.21(4) 0.06(2) 0.08(2) -0.033(19) 0.05(3) -0.06(2) C3 0.064(19) 0.09(2) 0.07(2) -0.011(18) -0.042(16) 0.037(16) C5 0.09(2) 0.09(3) 0.13(3) -0.03(2) -0.03(2) -0.03(2) C4 0.072(18) 0.053(18) 0.14(3) -0.024(17) -0.033(19) -0.041(15) C7 0.09(3) 0.10(2) 0.06(2) -0.003(18) -0.010(19) 0.00(2) C9 0.11(3) 0.024(13) 0.067(18) 0.015(13) 0.04(2) 0.024(15) C10 0.06(2) 0.09(3) 0.16(4) -0.03(3) -0.05(2) 0.02(2) F1 0.13(2) 0.14(2) 0.31(4) 0.00(2) 0.04(2) -0.021(17) F2 0.23(2) 0.078(13) 0.24(2) -0.042(15) -0.12(2) 0.028(16) F3 0.22(2) 0.111(17) 0.28(3) -0.002(17) -0.17(3) -0.076(16) O3 0.137(19) 0.22(3) 0.087(15) -0.050(17) 0.032(14) -0.09(2) C2 0.09(2) 0.044(17) 0.09(2) -0.020(17) -0.013(18) 0.010(15) _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 Zn N5 2.10(2) . ? Zn N5 2.10(2) 2_657 ? Zn N1 2.12(2) . ? Zn N1 2.12(2) 2_657 ? Zn N3 2.20(2) . ? Zn N3 2.20(2) 2_657 ? S O3 1.36(2) . ? S O2 1.412(19) . ? S O1 1.422(18) . ? S C10 1.71(4) . ? N5 C7 1.23(3) . ? N5 N6 1.44(2) . ? C6 C5 1.28(3) . ? C6 N4 1.30(3) . ? N2 C3 1.37(3) . ? N2 N1 1.40(2) . ? N2 C11 1.44(3) . ? N6 C9 1.31(2) . ? N6 C11 1.38(2) . ? C8 C7 1.37(3) . ? C8 C9 1.39(3) . ? C11 N4 1.40(2) . ? N1 C1 1.24(3) . ? N3 N4 1.34(2) . ? N3 C4 1.36(3) . ? C1 C2 1.59(4) . ? C3 C2 1.28(3) . ? C5 C4 1.37(3) . ? C10 F1 1.27(4) . ? C10 F2 1.28(3) . ? C10 F3 1.31(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 N5 Zn N5 180.000(3) . 2_657 ? N5 Zn N1 86.0(7) . . ? N5 Zn N1 94.0(7) 2_657 . ? N5 Zn N1 94.0(7) . 2_657 ? N5 Zn N1 86.0(7) 2_657 2_657 ? N1 Zn N1 180.0(11) . 2_657 ? N5 Zn N3 82.1(9) . . ? N5 Zn N3 97.9(9) 2_657 . ? N1 Zn N3 82.7(7) . . ? N1 Zn N3 97.3(7) 2_657 . ? N5 Zn N3 97.9(9) . 2_657 ? N5 Zn N3 82.1(9) 2_657 2_657 ? N1 Zn N3 97.3(7) . 2_657 ? N1 Zn N3 82.7(7) 2_657 2_657 ? N3 Zn N3 180.000(4) . 2_657 ? O3 S O2 111.1(15) . . ? O3 S O1 117.3(14) . . ? O2 S O1 116.3(15) . . ? O3 S C10 101.2(19) . . ? O2 S C10 104.8(16) . . ? O1 S C10 103.8(16) . . ? C7 N5 N6 104(2) . . ? C7 N5 Zn 138(2) . . ? N6 N5 Zn 117.8(15) . . ? C5 C6 N4 108(3) . . ? C3 N2 N1 107(2) . . ? C3 N2 C11 132(2) . . ? N1 N2 C11 120.0(19) . . ? C9 N6 C11 132(2) . . ? C9 N6 N5 110(2) . . ? C11 N6 N5 117(2) . . ? C7 C8 C9 105(2) . . ? N6 C11 N2 114.1(19) . . ? N6 C11 N4 113(2) . . ? N2 C11 N4 112.0(19) . . ? C1 N1 N2 115(3) . . ? C1 N1 Zn 130(2) . . ? N2 N1 Zn 115.6(14) . . ? N4 N3 C4 101(2) . . ? N4 N3 Zn 119.3(16) . . ? C4 N3 Zn 140(2) . . ? C6 N4 N3 114(2) . . ? C6 N4 C11 130(2) . . ? N3 N4 C11 116(2) . . ? N1 C1 C2 101(3) . . ? C2 C3 N2 108(2) . . ? C6 C5 C4 107(3) . . ? N3 C4 C5 110(3) . . ? N5 C7 C8 114(3) . . ? N6 C9 C8 106(2) . . ? F1 C10 F2 102(3) . . ? F1 C10 F3 107(3) . . ? F2 C10 F3 102(3) . . ? F1 C10 S 112(3) . . ? F2 C10 S 117(2) . . ? F3 C10 S 116(3) . . ? C3 C2 C1 109(2) . . ? _diffrn_measured_fraction_theta_max 0.942 _diffrn_reflns_theta_full 21.86 _diffrn_measured_fraction_theta_full 0.922 _refine_diff_density_max 0.655 _refine_diff_density_min -0.758 _refine_diff_density_rms 0.174 #===END data_comp-10 _database_code_depnum_ccdc_archive 'CCDC 790413' #TrackingRef '- threecomp.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '(C20 H24 N6 Ru 2+), (Cl -1), (O H -1), 2(H2 O)' _chemical_formula_sum 'C20 H29 Cl N6 O3 Ru' _chemical_formula_weight 538.01 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' Cl Cl 0.1484 0.1585 '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' 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 10.8075(10) _cell_length_b 11.1046(11) _cell_length_c 12.2293(15) _cell_angle_alpha 64.7100(10) _cell_angle_beta 87.8190(10) _cell_angle_gamma 62.4560(10) _cell_volume 1153.1(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4133 _cell_measurement_theta_min 2.31 _cell_measurement_theta_max 24.67 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.550 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.829 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.780 _exptl_absorpt_correction_T_max 0.856 _exptl_absorpt_process_details SADABS _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 'Bruker SMART Apex II CCD' _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 9892 _diffrn_reflns_av_R_equivalents 0.0189 _diffrn_reflns_av_sigmaI/netI 0.0324 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5149 _reflns_number_gt 4682 _reflns_threshold_expression >2\s(I) _computing_data_collection SMART _computing_cell_refinement SMART _computing_data_reduction SAINT+ _computing_structure_solution 'SIR-97 (Giacovazzo, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL99 (Keller 1999)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0814P)^2^+1.0040P] 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 5149 _refine_ls_number_parameters 281 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0435 _refine_ls_R_factor_gt 0.0398 _refine_ls_wR_factor_ref 0.1298 _refine_ls_wR_factor_gt 0.1273 _refine_ls_goodness_of_fit_ref 1.140 _refine_ls_restrained_S_all 1.140 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ru1 Ru 0.74523(2) 0.08788(3) 0.28400(2) 0.02438(11) Uani 1 1 d . . . N1 N 0.9334(3) 0.0243(3) 0.2136(3) 0.0313(6) Uani 1 1 d . . . N2 N 0.9604(3) 0.1334(3) 0.1284(3) 0.0319(6) Uani 1 1 d . . . N3 N 0.6521(3) 0.2520(3) 0.0970(3) 0.0285(6) Uani 1 1 d . . . N4 N 0.7233(3) 0.3214(3) 0.0270(2) 0.0287(6) Uani 1 1 d . . . N5 N 0.7852(3) 0.2580(3) 0.2818(3) 0.0288(6) Uani 1 1 d . . . N6 N 0.8334(3) 0.3304(3) 0.1843(3) 0.0304(6) Uani 1 1 d . . . C4 C 0.5358(4) 0.3029(4) 0.0187(3) 0.0322(7) Uani 1 1 d . . . H4 H 0.4655 0.2760 0.0407 0.039 Uiso 1 1 calc R . . C5 C 0.5341(4) 0.4012(4) -0.0998(3) 0.0348(7) Uani 1 1 d . . . H5 H 0.4651 0.4500 -0.1701 0.042 Uiso 1 1 calc R . . C6 C 0.6547(4) 0.4117(4) -0.0922(3) 0.0345(7) Uani 1 1 d . . . H6 H 0.6835 0.4696 -0.1565 0.041 Uiso 1 1 calc R . . C9 C 0.8542(4) 0.4357(4) 0.1961(4) 0.0371(8) Uani 1 1 d . . . H9 H 0.8870 0.4979 0.1412 0.045 Uiso 1 1 calc R . . C8 C 0.8169(5) 0.4319(5) 0.3060(4) 0.0425(9) Uani 1 1 d . . . H8 H 0.8199 0.4909 0.3406 0.051 Uiso 1 1 calc R . . C7 C 0.7738(4) 0.3223(4) 0.3549(3) 0.0363(8) Uani 1 1 d . . . H7 H 0.7415 0.2972 0.4287 0.044 Uiso 1 1 calc R . . C3 C 1.0854(4) 0.0710(5) 0.0956(4) 0.0412(9) Uani 1 1 d . . . H3 H 1.1250 0.1235 0.0390 0.049 Uiso 1 1 calc R . . C2 C 1.1435(4) -0.0839(5) 0.1606(5) 0.0485(10) Uani 1 1 d . . . H2 H 1.2300 -0.1577 0.1571 0.058 Uiso 1 1 calc R . . C1 C 1.0470(4) -0.1098(4) 0.2335(4) 0.0401(8) Uani 1 1 d . . . H1 H 1.0595 -0.2058 0.2879 0.048 Uiso 1 1 calc R . . C16 C 0.8084(6) -0.0060(6) 0.5904(4) 0.0570(12) Uani 1 1 d . . . H16A H 0.8062 -0.0796 0.6679 0.086 Uiso 1 1 calc R . . H16B H 0.7532 0.0948 0.5834 0.086 Uiso 1 1 calc R . . H16C H 0.9050 -0.0285 0.5861 0.086 Uiso 1 1 calc R . . C12 C 0.7470(4) -0.0132(5) 0.4868(3) 0.0388(8) Uani 1 1 d . . . C13 C 0.8298(4) -0.1296(4) 0.4552(3) 0.0389(8) Uani 1 1 d . . . H13 H 0.9237 -0.1993 0.4969 0.047 Uiso 1 1 calc R . . C14 C 0.7738(4) -0.1439(4) 0.3609(3) 0.0359(8) Uani 1 1 d . . . H14 H 0.8315 -0.2231 0.3424 0.043 Uiso 1 1 calc R . . C15 C 0.6327(4) -0.0403(4) 0.2951(3) 0.0308(7) Uani 1 1 d . . . C10 C 0.5483(4) 0.0825(4) 0.3252(3) 0.0318(7) Uani 1 1 d . . . H10 H 0.4550 0.1539 0.2824 0.038 Uiso 1 1 calc R . . C11 C 0.6045(4) 0.0957(5) 0.4176(3) 0.0363(8) Uani 1 1 d . . . H11 H 0.5486 0.1767 0.4346 0.044 Uiso 1 1 calc R . . C17 C 0.5717(4) -0.0577(4) 0.1967(4) 0.0375(8) Uani 1 1 d . . . H17 H 0.4901 0.0421 0.1420 0.045 Uiso 1 1 calc R . . C18 C 0.5169(6) -0.1698(7) 0.2593(6) 0.0643(14) Uani 1 1 d . . . H18A H 0.4897 -0.1929 0.2000 0.096 Uiso 1 1 calc R . . H18B H 0.4358 -0.1248 0.2923 0.096 Uiso 1 1 calc R . . H18C H 0.5905 -0.2624 0.3249 0.096 Uiso 1 1 calc R . . C19 C 0.6778(6) -0.1059(6) 0.1185(5) 0.0546(11) Uani 1 1 d . . . H19A H 0.7134 -0.0355 0.0843 0.082 Uiso 1 1 calc R . . H19B H 0.6316 -0.1057 0.0528 0.082 Uiso 1 1 calc R . . H19C H 0.7554 -0.2070 0.1689 0.082 Uiso 1 1 calc R . . C20 C 0.8557(4) 0.2917(4) 0.0840(3) 0.0300(7) Uani 1 1 d . . . H20 H 0.8896 0.3551 0.0225 0.036 Uiso 1 1 calc R . . Cl1 Cl 0.20783(11) 0.31020(13) 0.11711(10) 0.0500(3) Uani 1 1 d . . . O1 O 0.1001(3) 0.5235(2) 0.4391(2) 0.0319(5) Uani 1 1 d D . . H1A H 0.1246(3) 0.5822(3) 0.3844(2) 0.038 Uiso 1 1 d D . . O2W O 0.4296(3) 0.4655(3) 0.4270(2) 0.0618(9) Uani 1 1 d R . . H2W H 0.5041 0.3871 0.5016 0.074 Uiso 1 1 d R . . H21W H 0.4181 0.3987 0.4005 0.074 Uiso 1 1 d R . . O3W O 0.0491(3) 0.5924(3) 0.1681(2) 0.0619(9) Uani 1 1 d RD . . H3W H 0.0972 0.5043 0.1731 0.074 Uiso 1 1 d RD . . H31W H 0.0423 0.5805 0.2404 0.074 Uiso 1 1 d RD . . 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 0.02300(16) 0.02466(16) 0.02283(16) -0.00871(11) 0.00446(10) -0.01186(11) N1 0.0295(14) 0.0305(14) 0.0343(15) -0.0149(12) 0.0065(12) -0.0151(12) N2 0.0272(14) 0.0347(15) 0.0338(15) -0.0150(13) 0.0098(12) -0.0162(12) N3 0.0270(13) 0.0279(13) 0.0274(13) -0.0098(11) 0.0059(11) -0.0140(11) N4 0.0304(14) 0.0298(13) 0.0244(13) -0.0099(11) 0.0054(11) -0.0160(12) N5 0.0316(14) 0.0295(14) 0.0265(13) -0.0125(11) 0.0060(11) -0.0165(12) N6 0.0335(15) 0.0317(14) 0.0295(14) -0.0129(12) 0.0081(11) -0.0201(12) C4 0.0261(16) 0.0305(16) 0.0369(18) -0.0145(14) 0.0010(13) -0.0122(13) C5 0.0324(17) 0.0315(17) 0.0306(17) -0.0127(14) -0.0009(14) -0.0095(14) C6 0.0397(19) 0.0319(17) 0.0242(15) -0.0100(14) 0.0045(14) -0.0145(15) C9 0.0370(19) 0.0324(17) 0.044(2) -0.0157(16) 0.0026(16) -0.0203(15) C8 0.048(2) 0.0367(19) 0.046(2) -0.0219(17) 0.0007(17) -0.0202(17) C7 0.0397(19) 0.0348(17) 0.0320(17) -0.0166(15) 0.0035(15) -0.0154(15) C3 0.0338(18) 0.055(2) 0.052(2) -0.035(2) 0.0226(17) -0.0275(18) C2 0.0326(19) 0.053(2) 0.074(3) -0.043(2) 0.0225(19) -0.0196(18) C1 0.0300(18) 0.0341(18) 0.055(2) -0.0234(18) 0.0075(16) -0.0121(15) C16 0.074(3) 0.075(3) 0.0278(19) -0.017(2) 0.005(2) -0.048(3) C12 0.049(2) 0.047(2) 0.0214(15) -0.0081(15) 0.0073(15) -0.0322(19) C13 0.0369(19) 0.0354(18) 0.0321(18) -0.0034(15) -0.0029(15) -0.0190(16) C14 0.0355(18) 0.0247(16) 0.0384(19) -0.0061(14) 0.0063(15) -0.0156(14) C15 0.0328(17) 0.0311(16) 0.0308(16) -0.0109(14) 0.0082(13) -0.0206(14) C10 0.0262(16) 0.0342(17) 0.0341(17) -0.0133(14) 0.0123(13) -0.0169(14) C11 0.0403(19) 0.044(2) 0.0306(17) -0.0183(15) 0.0178(15) -0.0250(17) C17 0.0364(19) 0.0371(18) 0.043(2) -0.0196(16) 0.0063(15) -0.0198(16) C18 0.070(3) 0.073(3) 0.092(4) -0.050(3) 0.033(3) -0.056(3) C19 0.060(3) 0.071(3) 0.057(3) -0.044(3) 0.021(2) -0.037(2) C20 0.0301(16) 0.0324(16) 0.0300(16) -0.0132(14) 0.0093(13) -0.0186(14) Cl1 0.0416(5) 0.0525(6) 0.0476(6) -0.0165(5) 0.0067(4) -0.0230(5) O1 0.0378(13) 0.0175(10) 0.0248(11) -0.0102(9) -0.0050(9) -0.0009(9) O2W 0.0404(16) 0.065(2) 0.0554(19) -0.0097(16) 0.0170(14) -0.0243(16) O3W 0.076(2) 0.064(2) 0.0521(19) -0.0211(17) 0.0164(17) -0.0439(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 Ru1 N1 2.105(3) . ? Ru1 N5 2.114(3) . ? Ru1 N3 2.117(3) . ? Ru1 C10 2.191(3) . ? Ru1 C11 2.190(3) . ? Ru1 C14 2.196(3) . ? Ru1 C13 2.199(4) . ? Ru1 C15 2.225(3) . ? Ru1 C12 2.239(3) . ? N1 C1 1.344(5) . ? N1 N2 1.366(4) . ? N2 C3 1.340(5) . ? N2 C20 1.434(4) . ? N3 C4 1.337(4) . ? N3 N4 1.362(4) . ? N4 C6 1.351(4) . ? N4 C20 1.444(4) . ? N5 C7 1.335(4) . ? N5 N6 1.364(4) . ? N6 C9 1.352(4) . ? N6 C20 1.441(4) . ? C4 C5 1.386(5) . ? C4 H4 0.9300 . ? C5 C6 1.371(5) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C9 C8 1.378(6) . ? C9 H9 0.9300 . ? C8 C7 1.392(6) . ? C8 H8 0.9300 . ? C7 H7 0.9300 . ? C3 C2 1.362(6) . ? C3 H3 0.9300 . ? C2 C1 1.398(6) . ? C2 H2 0.9300 . ? C1 H1 0.9300 . ? C16 C12 1.501(5) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C12 C13 1.396(6) . ? C12 C11 1.433(6) . ? C13 C14 1.422(5) . ? C13 H13 0.9300 . ? C14 C15 1.406(5) . ? C14 H14 0.9300 . ? C15 C10 1.443(5) . ? C15 C17 1.515(5) . ? C10 C11 1.394(5) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C17 C19 1.517(6) . ? C17 C18 1.523(6) . ? C17 H17 0.9800 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20 0.9800 . ? O1 H1A 0.846(3) . ? O2W H2W 0.9830 . ? O2W H21W 0.9829 . ? O3W H3W 0.8441 . ? O3W H31W 0.8415 . ? 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 N1 Ru1 N5 83.55(11) . . ? N1 Ru1 N3 82.88(11) . . ? N5 Ru1 N3 81.61(11) . . ? N1 Ru1 C10 152.80(13) . . ? N5 Ru1 C10 122.69(12) . . ? N3 Ru1 C10 93.31(12) . . ? N1 Ru1 C11 159.86(14) . . ? N5 Ru1 C11 96.23(13) . . ? N3 Ru1 C11 117.08(13) . . ? C10 Ru1 C11 37.12(14) . . ? N1 Ru1 C14 91.97(13) . . ? N5 Ru1 C14 154.68(13) . . ? N3 Ru1 C14 122.67(13) . . ? C10 Ru1 C14 67.43(13) . . ? C11 Ru1 C14 79.61(15) . . ? N1 Ru1 C13 95.20(13) . . ? N5 Ru1 C13 117.65(13) . . ? N3 Ru1 C13 160.41(13) . . ? C10 Ru1 C13 79.47(14) . . ? C11 Ru1 C13 66.98(15) . . ? C14 Ru1 C13 37.75(14) . . ? N1 Ru1 C15 115.18(12) . . ? N5 Ru1 C15 160.67(13) . . ? N3 Ru1 C15 95.43(12) . . ? C10 Ru1 C15 38.13(13) . . ? C11 Ru1 C15 67.98(14) . . ? C14 Ru1 C15 37.08(13) . . ? C13 Ru1 C15 67.64(13) . . ? N1 Ru1 C12 122.14(14) . . ? N5 Ru1 C12 94.03(13) . . ? N3 Ru1 C12 154.15(14) . . ? C10 Ru1 C12 67.54(14) . . ? C11 Ru1 C12 37.72(15) . . ? C14 Ru1 C12 67.33(15) . . ? C13 Ru1 C12 36.65(15) . . ? C15 Ru1 C12 80.27(13) . . ? C1 N1 N2 104.8(3) . . ? C1 N1 Ru1 134.7(3) . . ? N2 N1 Ru1 120.5(2) . . ? C3 N2 N1 111.8(3) . . ? C3 N2 C20 129.4(3) . . ? N1 N2 C20 118.8(3) . . ? C4 N3 N4 104.8(3) . . ? C4 N3 Ru1 135.3(2) . . ? N4 N3 Ru1 119.6(2) . . ? C6 N4 N3 111.6(3) . . ? C6 N4 C20 129.0(3) . . ? N3 N4 C20 119.4(3) . . ? C7 N5 N6 104.8(3) . . ? C7 N5 Ru1 136.2(3) . . ? N6 N5 Ru1 119.0(2) . . ? C9 N6 N5 112.2(3) . . ? C9 N6 C20 127.5(3) . . ? N5 N6 C20 120.3(3) . . ? N3 C4 C5 111.0(3) . . ? N3 C4 H4 124.5 . . ? C5 C4 H4 124.5 . . ? C6 C5 C4 106.0(3) . . ? C6 C5 H5 127.0 . . ? C4 C5 H5 127.0 . . ? N4 C6 C5 106.6(3) . . ? N4 C6 H6 126.7 . . ? C5 C6 H6 126.7 . . ? N6 C9 C8 105.9(3) . . ? N6 C9 H9 127.0 . . ? C8 C9 H9 127.0 . . ? C9 C8 C7 106.2(3) . . ? C9 C8 H8 126.9 . . ? C7 C8 H8 126.9 . . ? N5 C7 C8 110.9(3) . . ? N5 C7 H7 124.6 . . ? C8 C7 H7 124.6 . . ? N2 C3 C2 107.1(3) . . ? N2 C3 H3 126.4 . . ? C2 C3 H3 126.4 . . ? C3 C2 C1 106.2(3) . . ? C3 C2 H2 126.9 . . ? C1 C2 H2 126.9 . . ? N1 C1 C2 110.2(4) . . ? N1 C1 H1 124.9 . . ? C2 C1 H1 124.9 . . ? C12 C16 H16A 109.5 . . ? C12 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C12 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C13 C12 C11 117.8(3) . . ? C13 C12 C16 119.8(4) . . ? C11 C12 C16 122.4(4) . . ? C13 C12 Ru1 70.1(2) . . ? C11 C12 Ru1 69.28(19) . . ? C16 C12 Ru1 132.3(3) . . ? C12 C13 C14 121.5(3) . . ? C12 C13 Ru1 73.2(2) . . ? C14 C13 Ru1 71.0(2) . . ? C12 C13 H13 119.2 . . ? C14 C13 H13 119.2 . . ? Ru1 C13 H13 128.9 . . ? C15 C14 C13 121.1(4) . . ? C15 C14 Ru1 72.56(19) . . ? C13 C14 Ru1 71.2(2) . . ? C15 C14 H14 119.5 . . ? C13 C14 H14 119.5 . . ? Ru1 C14 H14 129.2 . . ? C14 C15 C10 117.5(3) . . ? C14 C15 C17 121.1(3) . . ? C10 C15 C17 121.4(3) . . ? C14 C15 Ru1 70.36(19) . . ? C10 C15 Ru1 69.65(19) . . ? C17 C15 Ru1 131.4(2) . . ? C11 C10 C15 120.9(3) . . ? C11 C10 Ru1 71.4(2) . . ? C15 C10 Ru1 72.23(18) . . ? C11 C10 H10 119.5 . . ? C15 C10 H10 119.5 . . ? Ru1 C10 H10 129.3 . . ? C10 C11 C12 121.2(4) . . ? C10 C11 Ru1 71.46(19) . . ? C12 C11 Ru1 73.0(2) . . ? C10 C11 H11 119.4 . . ? C12 C11 H11 119.4 . . ? Ru1 C11 H11 128.4 . . ? C15 C17 C19 112.7(3) . . ? C15 C17 C18 108.4(4) . . ? C19 C17 C18 112.1(4) . . ? C15 C17 H17 107.8 . . ? C19 C17 H17 107.8 . . ? C18 C17 H17 107.8 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N2 C20 N6 110.2(3) . . ? N2 C20 N4 109.8(3) . . ? N6 C20 N4 109.8(3) . . ? N2 C20 H20 109.0 . . ? N6 C20 H20 109.0 . . ? N4 C20 H20 109.0 . . ? H2W O2W H21W 99.5 . . ? H3W O3W H31W 107.1 . . ? _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 1.704 _refine_diff_density_min -0.494 _refine_diff_density_rms 0.140 #===END #===END data_tpetoh _database_code_depnum_ccdc_archive 'CCDC 790414' #TrackingRef '- threecomp.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H12 N6 O' _chemical_formula_weight 244.27 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 19.6841(11) _cell_length_b 11.6982(6) _cell_length_c 12.5672(7) _cell_angle_alpha 90.00 _cell_angle_beta 125.6120(10) _cell_angle_gamma 90.00 _cell_volume 2352.6(2) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2024 _cell_measurement_theta_min 2.57 _cell_measurement_theta_max 23.55 _exptl_crystal_description block _exptl_crystal_colour white _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.379 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1024 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.965 _exptl_absorpt_correction_T_max 0.981 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'Bruker SMART Apex II CCD' _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 13081 _diffrn_reflns_av_R_equivalents 0.0158 _diffrn_reflns_av_sigmaI/netI 0.0115 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 27.98 _reflns_number_total 2794 _reflns_number_gt 2481 _reflns_threshold_expression >2\s(I) _computing_data_collection SMART _computing_cell_refinement SMART _computing_data_reduction SAINT+ _computing_structure_solution 'SIR-97 (Giacovazzo, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL99 (Keller 1999)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0737P)^2^+0.6254P] 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 2794 _refine_ls_number_parameters 167 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0480 _refine_ls_R_factor_gt 0.0441 _refine_ls_wR_factor_ref 0.1229 _refine_ls_wR_factor_gt 0.1186 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.061 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.18424(6) 0.88383(8) 0.30544(9) 0.0400(2) Uani 1 1 d . . . N2 N 0.16973(8) 0.88720(9) 0.39904(11) 0.0540(3) Uani 1 1 d . . . N3 N 0.14781(6) 1.07194(8) 0.22619(9) 0.0400(2) Uani 1 1 d . . . N4 N 0.16301(7) 1.17860(9) 0.20196(12) 0.0516(3) Uani 1 1 d . . . N5 N 0.28831(6) 1.03009(8) 0.39885(9) 0.0421(2) Uani 1 1 d . . . N6 N 0.36355(7) 0.98767(11) 0.43804(12) 0.0607(3) Uani 1 1 d . . . O1 O 0.16224(5) 0.94019(8) 0.05464(8) 0.0482(2) Uani 1 1 d D . . C1 C 0.23495(7) 0.96216(10) 0.18004(10) 0.0411(2) Uani 1 1 d . . . H1A H 0.2638 1.0276 0.1764 0.049 Uiso 1 1 calc R . . H1B H 0.2720 0.8967 0.2096 0.049 Uiso 1 1 calc R . . C2 C 0.21345(6) 0.98631(9) 0.27811(10) 0.0371(2) Uani 1 1 d . . . C3 C 0.15959(8) 0.78322(9) 0.24020(12) 0.0459(3) Uani 1 1 d . . . H3 H 0.1628 0.7623 0.1718 0.055 Uiso 1 1 calc R . . C6 C 0.06605(8) 1.05602(11) 0.17298(13) 0.0515(3) Uani 1 1 d . . . H6 H 0.0412 0.9892 0.1751 0.062 Uiso 1 1 calc R . . C8 C 0.08891(8) 1.22866(11) 0.13566(13) 0.0510(3) Uani 1 1 d . . . H8 H 0.0797 1.3038 0.1060 0.061 Uiso 1 1 calc R . . C7 C 0.02687(8) 1.15657(12) 0.11554(14) 0.0577(3) Uani 1 1 d . . . H7 H -0.0296 1.1732 0.0720 0.069 Uiso 1 1 calc R . . C4 C 0.12926(10) 0.71840(11) 0.29368(15) 0.0585(3) Uani 1 1 d . . . H4 H 0.1078 0.6446 0.2700 0.070 Uiso 1 1 calc R . . C5 C 0.13712(11) 0.78590(12) 0.39121(15) 0.0623(4) Uani 1 1 d . . . H5 H 0.1213 0.7627 0.4447 0.075 Uiso 1 1 calc R . . C9 C 0.29556(8) 1.10792(11) 0.48408(12) 0.0510(3) Uani 1 1 d . . . H9 H 0.2522 1.1477 0.4770 0.061 Uiso 1 1 calc R . . C10 C 0.37825(9) 1.11709(13) 0.58230(13) 0.0614(4) Uani 1 1 d . . . H10 H 0.4031 1.1640 0.6556 0.074 Uiso 1 1 calc R . . C11 C 0.41747(10) 1.04140(14) 0.54965(15) 0.0667(4) Uani 1 1 d . . . H11 H 0.4749 1.0297 0.6002 0.080 Uiso 1 1 calc R . . H1 H 0.1603(11) 0.9915(15) 0.0021(17) 0.078(5) Uiso 1 1 d 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 N1 0.0504(5) 0.0362(5) 0.0394(4) -0.0021(3) 0.0297(4) -0.0026(4) N2 0.0803(7) 0.0492(6) 0.0503(6) -0.0038(4) 0.0482(6) -0.0076(5) N3 0.0432(5) 0.0360(5) 0.0459(5) -0.0010(3) 0.0288(4) -0.0013(3) N4 0.0558(6) 0.0391(5) 0.0697(7) 0.0060(5) 0.0421(6) 0.0010(4) N5 0.0447(5) 0.0409(5) 0.0403(5) -0.0067(4) 0.0245(4) -0.0030(4) N6 0.0440(6) 0.0648(7) 0.0558(6) -0.0148(5) 0.0190(5) 0.0040(5) O1 0.0532(5) 0.0536(5) 0.0378(4) -0.0029(3) 0.0264(4) -0.0077(4) C1 0.0431(6) 0.0460(6) 0.0395(5) -0.0034(4) 0.0270(5) -0.0031(4) C2 0.0404(5) 0.0358(5) 0.0374(5) -0.0031(4) 0.0240(4) -0.0024(4) C3 0.0550(6) 0.0373(5) 0.0510(6) -0.0059(4) 0.0340(5) -0.0029(4) C6 0.0430(6) 0.0472(6) 0.0612(7) -0.0052(5) 0.0285(6) -0.0064(5) C8 0.0603(7) 0.0431(6) 0.0534(7) 0.0040(5) 0.0353(6) 0.0086(5) C7 0.0443(6) 0.0566(7) 0.0614(8) -0.0040(6) 0.0247(6) 0.0041(5) C4 0.0733(8) 0.0409(6) 0.0728(8) -0.0037(6) 0.0490(7) -0.0102(6) C5 0.0869(10) 0.0550(8) 0.0676(8) 0.0027(6) 0.0578(8) -0.0096(7) C9 0.0631(7) 0.0506(7) 0.0508(6) -0.0148(5) 0.0397(6) -0.0121(5) C10 0.0693(8) 0.0656(8) 0.0479(7) -0.0189(6) 0.0333(7) -0.0226(7) C11 0.0503(7) 0.0747(9) 0.0536(8) -0.0135(7) 0.0181(6) -0.0068(6) _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 C3 1.3525(14) . ? N1 N2 1.3631(13) . ? N1 C2 1.4546(13) . ? N2 C5 1.3238(18) . ? N3 C6 1.3486(15) . ? N3 N4 1.3584(13) . ? N3 C2 1.4549(13) . ? N4 C8 1.3226(16) . ? N5 C9 1.3486(14) . ? N5 N6 1.3538(15) . ? N5 C2 1.4602(13) . ? N6 C11 1.3249(18) . ? O1 C1 1.4040(14) . ? C1 C2 1.5446(14) . ? C3 C4 1.3604(18) . ? C6 C7 1.3606(19) . ? C8 C7 1.3810(19) . ? C4 C5 1.389(2) . ? C9 C10 1.358(2) . ? C10 C11 1.385(2) . ? 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 C3 N1 N2 111.52(9) . . ? C3 N1 C2 128.73(9) . . ? N2 N1 C2 119.35(9) . . ? C5 N2 N1 104.25(10) . . ? C6 N3 N4 111.76(10) . . ? C6 N3 C2 128.24(9) . . ? N4 N3 C2 118.62(9) . . ? C8 N4 N3 103.99(10) . . ? C9 N5 N6 111.79(10) . . ? C9 N5 C2 129.65(10) . . ? N6 N5 C2 118.54(9) . . ? C11 N6 N5 104.09(11) . . ? O1 C1 C2 110.81(9) . . ? N3 C2 N1 107.67(8) . . ? N3 C2 N5 108.66(8) . . ? N1 C2 N5 110.01(9) . . ? N3 C2 C1 110.64(9) . . ? N1 C2 C1 111.55(8) . . ? N5 C2 C1 108.28(8) . . ? N1 C3 C4 106.93(10) . . ? N3 C6 C7 106.73(11) . . ? N4 C8 C7 112.23(11) . . ? C6 C7 C8 105.26(11) . . ? C3 C4 C5 105.29(11) . . ? N2 C5 C4 112.00(11) . . ? N5 C9 C10 106.95(12) . . ? C9 C10 C11 105.08(12) . . ? N6 C11 C10 112.09(13) . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 27.98 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.259 _refine_diff_density_min -0.335 _refine_diff_density_rms 0.075