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 'Chakraborty, Soma' 'Gonnade, Rajesh G.' 'Lahiri, Goutam Kumar' 'Laye, Rebecca H.' 'Paul, Rowena L.' 'Puranik, Vedavati G.' 'Ward, Mike' _publ_contact_author_name 'Prof Goutam Kumar Lahiri' _publ_contact_author_address ; Chemistry IIT, Bombay Dept. of Chemistry Indian Institute of Technology, Bom Powai Mumbai Maharashtra 400 076 INDIA ; _publ_contact_author_email 'LAHIRI@ETHER.CHEM.IITB.AC.IN' _publ_section_title ; A dinuclear bis(bipyridine)ruthenium(II) complex [(bpy)2RuII{L2-}RuII(bpy)2]2+ incorporating an unusual non-innocent bridging ligand containing a p-benzoquinonediimine fragment: synthesis, structure, redox, UV/VIS/NIR, EPR and spectroelectrochemical properties. ; data_compound1 _database_code_CSD 164245 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C52 H44 Cl2 N10 O12 Ru2' _chemical_formula_weight 1274.01 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 '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 12.320(4) _cell_length_b 14.781(5) _cell_length_c 15.394(5) _cell_angle_alpha 83.096(5) _cell_angle_beta 77.626(5) _cell_angle_gamma 73.646(5) _cell_volume 2622.1(14) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour 'dark purple' _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.614 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1288 _exptl_absorpt_coefficient_mu 0.751 _exptl_absorpt_correction_type 'Empirical, pseudo-azimuthal scan (SADABS)' _exptl_absorpt_correction_T_min 0.91 _exptl_absorpt_correction_T_max 0.93 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 SMART Area Detector' _diffrn_measurement_method '\w rotation with narrow frames (0.3 degrees)' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22478 _diffrn_reflns_av_R_equivalents 0.0843 _diffrn_reflns_av_sigmaI/netI 0.1320 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.44 _diffrn_reflns_theta_max 25.00 _reflns_number_total 9228 _reflns_number_gt 4818 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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^)+(0.1377P)^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 9228 _refine_ls_number_parameters 703 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1560 _refine_ls_R_factor_gt 0.0772 _refine_ls_wR_factor_ref 0.2376 _refine_ls_wR_factor_gt 0.1912 _refine_ls_goodness_of_fit_ref 0.957 _refine_ls_restrained_S_all 0.957 _refine_ls_shift/su_max 0.008 _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 0.74584(6) 1.14916(6) 0.15416(5) 0.0390(3) Uani 1 1 d . . . Ru2 Ru 0.72847(7) 0.65667(6) 0.34664(5) 0.0491(3) Uani 1 1 d . . . Cl1 Cl 0.8940(3) 0.9225(3) 0.63634(19) 0.0720(9) Uani 1 1 d . . . O11 O 0.9415(10) 0.8944(17) 0.5556(9) 0.241(11) Uani 1 1 d . . . O12 O 0.884(2) 0.8362(13) 0.6866(14) 0.278(13) Uani 1 1 d . . . O13 O 0.9653(7) 0.9613(7) 0.6754(6) 0.091(3) Uani 1 1 d . . . O14 O 0.7884(9) 0.9744(13) 0.6449(12) 0.213(10) Uani 1 1 d . . . Cl2 Cl 0.3585(3) 0.2880(3) 0.0712(3) 0.1117(15) Uani 1 1 d . . . O21 O 0.3659(12) 0.1946(12) 0.096(2) 0.330(17) Uani 1 1 d . . . O22 O 0.4463(15) 0.3038(17) 0.0120(13) 0.271(11) Uani 1 1 d . . . O23 O 0.384(3) 0.333(4) 0.151(2) 0.65(3) Uani 1 1 d . . . O24 O 0.2433(9) 0.3487(9) 0.0754(10) 0.155(5) Uani 1 1 d . . . N11 N 0.8197(9) 0.5457(8) 0.4186(6) 0.065(3) Uani 1 1 d . . . N21 N 0.8028(7) 0.5641(6) 0.2502(6) 0.055(2) Uani 1 1 d . . . N31 N 0.8627(6) 0.7164(5) 0.3260(5) 0.0370(18) Uani 1 1 d . . . N41 N 0.6714(7) 0.7524(8) 0.4409(6) 0.067(3) Uani 1 1 d . . . N51 N 0.7428(7) 1.1913(7) 0.2762(6) 0.056(2) Uani 1 1 d . . . N61 N 0.6879(7) 1.2922(6) 0.1358(7) 0.056(2) Uani 1 1 d . . . N71 N 0.9112(6) 1.1546(5) 0.0988(5) 0.0375(18) Uani 1 1 d . . . N81 N 0.7608(7) 1.1139(5) 0.0265(5) 0.0396(19) Uani 1 1 d . . . N91 N 0.5897(6) 1.1267(6) 0.1973(5) 0.046(2) Uani 1 1 d . . . H91 H 0.5265 1.1736 0.2035 0.056 Uiso 1 1 calc R . . N101 N 0.6139(6) 0.7495(6) 0.2747(5) 0.044(2) Uani 1 1 d . . . C12 C 0.8752(13) 0.4687(10) 0.3721(9) 0.080(4) Uani 1 1 d . . . C13 C 0.9344(12) 0.3841(10) 0.4133(11) 0.095(5) Uani 1 1 d . . . H13 H 0.9731 0.3303 0.3799 0.115 Uiso 1 1 calc R . . C14 C 0.9348(19) 0.3811(14) 0.5025(14) 0.126(8) Uani 1 1 d . . . H14 H 0.9744 0.3251 0.5317 0.152 Uiso 1 1 calc R . . C15 C 0.8778(16) 0.4591(15) 0.5493(12) 0.116(7) Uani 1 1 d . . . H15 H 0.8776 0.4565 0.6113 0.139 Uiso 1 1 calc R . . C16 C 0.8186(13) 0.5447(12) 0.5068(9) 0.097(5) Uani 1 1 d . . . H16 H 0.7798 0.5990 0.5394 0.116 Uiso 1 1 calc R . . C22 C 0.8738(11) 0.4791(8) 0.2761(8) 0.063(3) Uani 1 1 d . . . C23 C 0.9362(13) 0.4142(9) 0.2165(10) 0.086(4) Uani 1 1 d . . . H23 H 0.9830 0.3558 0.2363 0.103 Uiso 1 1 calc R . . C24 C 0.9313(12) 0.4334(9) 0.1252(10) 0.084(4) Uani 1 1 d . . . H24 H 0.9752 0.3893 0.0824 0.101 Uiso 1 1 calc R . . C25 C 0.8605(11) 0.5185(9) 0.1003(9) 0.071(3) Uani 1 1 d . . . H25 H 0.8541 0.5342 0.0396 0.085 Uiso 1 1 calc R . . C26 C 0.7998(9) 0.5799(7) 0.1640(7) 0.051(3) Uani 1 1 d . . . H26 H 0.7519 0.6383 0.1452 0.061 Uiso 1 1 calc R . . C32 C 0.8498(8) 0.7891(7) 0.3766(6) 0.044(2) Uani 1 1 d . . . C33 C 0.9354(9) 0.8360(7) 0.3694(7) 0.049(3) Uani 1 1 d . . . H33 H 0.9240 0.8870 0.4054 0.058 Uiso 1 1 calc R . . C34 C 1.0336(9) 0.8079(8) 0.3109(8) 0.058(3) Uani 1 1 d . . . H34 H 1.0924 0.8395 0.3051 0.069 Uiso 1 1 calc R . . C35 C 1.0507(8) 0.7326(8) 0.2580(7) 0.052(3) Uani 1 1 d . . . H35 H 1.1204 0.7122 0.2165 0.062 Uiso 1 1 calc R . . C36 C 0.9630(8) 0.6890(7) 0.2683(7) 0.049(3) Uani 1 1 d . . . H36 H 0.9738 0.6375 0.2331 0.058 Uiso 1 1 calc R . . C42 C 0.7392(9) 0.8118(8) 0.4386(6) 0.056(3) Uani 1 1 d . . . C43 C 0.7011(12) 0.8881(11) 0.4920(8) 0.089(4) Uani 1 1 d . . . H43 H 0.7463 0.9313 0.4892 0.107 Uiso 1 1 calc R . . C44 C 0.5954(13) 0.8997(14) 0.5498(10) 0.113(6) Uani 1 1 d . . . H44 H 0.5688 0.9503 0.5884 0.136 Uiso 1 1 calc R . . C45 C 0.5289(13) 0.8384(17) 0.5515(11) 0.138(8) Uani 1 1 d . . . H45 H 0.4559 0.8467 0.5901 0.166 Uiso 1 1 calc R . . C46 C 0.5699(12) 0.7660(13) 0.4967(9) 0.101(5) Uani 1 1 d . . . H46 H 0.5244 0.7233 0.4981 0.121 Uiso 1 1 calc R . . C52 C 0.6997(10) 1.2839(11) 0.2896(9) 0.075(4) Uani 1 1 d . . . C53 C 0.6899(12) 1.3154(15) 0.3741(13) 0.117(8) Uani 1 1 d . . . H53 H 0.6573 1.3806 0.3838 0.140 Uiso 1 1 calc R . . C54 C 0.7257(15) 1.255(2) 0.4428(12) 0.137(11) Uani 1 1 d . . . H54 H 0.7179 1.2765 0.5001 0.164 Uiso 1 1 calc R . . C55 C 0.7713(13) 1.1666(14) 0.4257(8) 0.096(6) Uani 1 1 d . . . H55 H 0.7999 1.1234 0.4716 0.115 Uiso 1 1 calc R . . C56 C 0.7798(9) 1.1326(11) 0.3432(7) 0.069(4) Uani 1 1 d . . . H56 H 0.8122 1.0672 0.3345 0.082 Uiso 1 1 calc R . . C62 C 0.6671(10) 1.3415(10) 0.2087(11) 0.079(4) Uani 1 1 d . . . C63 C 0.6198(13) 1.4407(12) 0.2002(16) 0.119(7) Uani 1 1 d . . . H63 H 0.6029 1.4769 0.2507 0.143 Uiso 1 1 calc R . . C64 C 0.5982(15) 1.4846(13) 0.120(2) 0.140(10) Uani 1 1 d . . . H64 H 0.5649 1.5508 0.1150 0.168 Uiso 1 1 calc R . . C65 C 0.6240(12) 1.4343(10) 0.0489(14) 0.105(6) Uani 1 1 d . . . H65 H 0.6111 1.4645 -0.0074 0.127 Uiso 1 1 calc R . . C66 C 0.6692(10) 1.3389(8) 0.0574(10) 0.072(4) Uani 1 1 d . . . H66 H 0.6883 1.3039 0.0059 0.086 Uiso 1 1 calc R . . C72 C 0.9488(9) 1.1326(6) 0.0115(6) 0.043(2) Uani 1 1 d . . . C73 C 1.0549(10) 1.1345(7) -0.0341(7) 0.057(3) Uani 1 1 d . . . H73 H 1.0788 1.1174 -0.0942 0.069 Uiso 1 1 calc R . . C74 C 1.1287(10) 1.1621(7) 0.0081(8) 0.062(3) Uani 1 1 d . . . H74 H 1.2024 1.1663 -0.0237 0.074 Uiso 1 1 calc R . . C75 C 1.0946(9) 1.1830(7) 0.0960(7) 0.050(3) Uani 1 1 d . . . H75 H 1.1452 1.1997 0.1262 0.060 Uiso 1 1 calc R . . C76 C 0.9849(8) 1.1794(6) 0.1400(7) 0.042(2) Uani 1 1 d . . . H76 H 0.9606 1.1946 0.2006 0.051 Uiso 1 1 calc R . . C82 C 0.8640(9) 1.1043(6) -0.0266(6) 0.044(2) Uani 1 1 d . . . C83 C 0.8885(11) 1.0709(6) -0.1129(7) 0.056(3) Uani 1 1 d . . . H83 H 0.9622 1.0648 -0.1499 0.068 Uiso 1 1 calc R . . C84 C 0.8022(13) 1.0475(8) -0.1413(7) 0.068(4) Uani 1 1 d . . . H84 H 0.8161 1.0247 -0.1989 0.082 Uiso 1 1 calc R . . C85 C 0.6974(13) 1.0568(8) -0.0880(8) 0.068(4) Uani 1 1 d . . . H85 H 0.6382 1.0401 -0.1080 0.082 Uiso 1 1 calc R . . C86 C 0.6766(10) 1.0909(7) -0.0035(7) 0.052(3) Uani 1 1 d . . . H86 H 0.6026 1.0980 0.0334 0.062 Uiso 1 1 calc R . . C92 C 0.5867(7) 1.0371(7) 0.2160(6) 0.038(2) Uani 1 1 d . . . C93 C 0.4849(8) 1.0043(8) 0.2416(6) 0.048(3) Uani 1 1 d . . . H93 H 0.4114 1.0486 0.2463 0.058 Uiso 1 1 calc R . . C94 C 0.4921(8) 0.9107(7) 0.2592(7) 0.047(3) Uani 1 1 d . . . H94 H 0.4239 0.8899 0.2765 0.056 Uiso 1 1 calc R . . C95 C 0.6064(8) 0.8414(7) 0.2515(6) 0.039(2) Uani 1 1 d . . . C96 C 0.7041(7) 0.8760(7) 0.2280(5) 0.038(2) Uani 1 1 d . . . H96 H 0.7775 0.8319 0.2246 0.045 Uiso 1 1 calc R . . C97 C 0.6999(7) 0.9701(6) 0.2094(5) 0.034(2) Uani 1 1 d . . . C102 C 0.5211(8) 0.7106(8) 0.2716(8) 0.055(3) Uani 1 1 d . . . C103 C 0.4523(8) 0.7386(8) 0.2066(8) 0.056(3) Uani 1 1 d . . . H103 H 0.4656 0.7866 0.1620 0.068 Uiso 1 1 calc R . . C104 C 0.3659(10) 0.6969(10) 0.2071(11) 0.080(4) Uani 1 1 d . . . H104 H 0.3212 0.7140 0.1616 0.096 Uiso 1 1 calc R . . C105 C 0.3442(11) 0.6295(10) 0.2745(12) 0.086(5) Uani 1 1 d . . . H105 H 0.2800 0.6048 0.2780 0.103 Uiso 1 1 calc R . . C106 C 0.4145(11) 0.5977(9) 0.3366(9) 0.077(4) Uani 1 1 d . . . H106 H 0.3988 0.5512 0.3822 0.093 Uiso 1 1 calc R . . C107 C 0.5099(10) 0.6345(9) 0.3326(8) 0.063(3) Uani 1 1 d . . . O98 O 0.7902(5) 1.0039(4) 0.1886(4) 0.0374(15) Uani 1 1 d . . . O108 O 0.5892(7) 0.5986(6) 0.3840(5) 0.078(3) Uani 1 1 d . . . O30 O 0.774(2) 0.6980(14) 0.6770(11) 0.241(9) Uani 1 1 d . . . O31 O 0.1776(13) 0.4863(10) 0.1957(16) 0.251(11) 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 Ru1 0.0364(5) 0.0399(5) 0.0409(5) -0.0077(3) -0.0089(3) -0.0071(4) Ru2 0.0492(5) 0.0641(6) 0.0426(5) 0.0172(4) -0.0121(4) -0.0349(5) Cl1 0.066(2) 0.104(3) 0.0489(17) -0.0150(17) -0.0156(14) -0.0181(19) O11 0.098(9) 0.53(3) 0.107(10) -0.161(16) 0.005(8) -0.064(14) O12 0.49(4) 0.183(17) 0.28(2) 0.121(16) -0.23(2) -0.22(2) O13 0.072(6) 0.142(9) 0.079(6) -0.011(6) -0.030(5) -0.049(6) O14 0.058(7) 0.29(2) 0.30(2) -0.220(18) -0.068(9) 0.049(9) Cl2 0.076(3) 0.106(3) 0.146(4) 0.047(3) -0.020(3) -0.037(2) O21 0.109(11) 0.164(15) 0.71(5) 0.24(2) -0.172(19) -0.063(10) O22 0.165(15) 0.35(3) 0.228(19) 0.098(18) 0.068(14) -0.078(16) O23 0.38(3) 1.48(10) 0.34(3) -0.35(6) -0.06(3) -0.505 O24 0.079(7) 0.132(10) 0.250(15) 0.080(10) -0.091(9) -0.014(7) N11 0.086(7) 0.086(8) 0.048(6) 0.027(5) -0.023(5) -0.066(7) N21 0.055(5) 0.047(5) 0.068(6) 0.028(4) -0.031(5) -0.019(4) N31 0.038(5) 0.037(5) 0.037(4) 0.012(4) -0.013(4) -0.013(4) N41 0.038(5) 0.119(9) 0.049(5) 0.004(5) -0.004(4) -0.035(6) N51 0.035(5) 0.087(8) 0.053(6) -0.030(5) 0.000(4) -0.025(5) N61 0.032(5) 0.045(5) 0.089(7) -0.024(5) -0.009(5) 0.002(4) N71 0.041(4) 0.019(4) 0.048(5) 0.006(3) -0.007(4) -0.006(3) N81 0.050(5) 0.029(4) 0.035(4) 0.005(3) -0.020(4) 0.004(4) N91 0.031(4) 0.048(5) 0.061(5) -0.019(4) -0.013(4) -0.002(4) N101 0.032(4) 0.056(6) 0.045(5) 0.000(4) -0.001(4) -0.019(4) C12 0.114(11) 0.077(9) 0.082(9) 0.057(8) -0.064(9) -0.070(9) C13 0.098(11) 0.073(9) 0.141(14) 0.056(9) -0.080(10) -0.047(8) C14 0.173(19) 0.111(14) 0.149(18) 0.105(13) -0.118(16) -0.104(15) C15 0.131(15) 0.154(17) 0.101(13) 0.097(13) -0.078(12) -0.100(15) C16 0.115(11) 0.142(14) 0.068(9) 0.051(9) -0.036(8) -0.097(11) C22 0.082(9) 0.044(7) 0.083(9) 0.025(6) -0.045(7) -0.038(6) C23 0.117(12) 0.042(8) 0.114(12) 0.020(8) -0.061(10) -0.027(8) C24 0.093(10) 0.050(8) 0.109(12) -0.019(8) -0.044(9) 0.008(7) C25 0.085(9) 0.059(8) 0.078(9) 0.002(7) -0.035(7) -0.022(7) C26 0.053(7) 0.041(6) 0.063(7) 0.007(6) -0.026(6) -0.012(5) C32 0.041(6) 0.058(7) 0.034(5) 0.017(5) -0.017(4) -0.016(5) C33 0.059(7) 0.056(7) 0.044(6) 0.014(5) -0.024(5) -0.033(6) C34 0.055(7) 0.061(8) 0.068(7) 0.043(6) -0.037(6) -0.035(6) C35 0.036(6) 0.064(8) 0.051(6) 0.018(6) -0.009(5) -0.015(5) C36 0.045(6) 0.042(6) 0.056(6) 0.019(5) -0.017(5) -0.010(5) C42 0.058(7) 0.077(8) 0.034(6) -0.002(5) -0.015(5) -0.017(6) C43 0.081(10) 0.128(13) 0.069(9) -0.026(9) -0.027(8) -0.026(9) C44 0.064(10) 0.175(18) 0.088(11) -0.083(11) 0.005(8) 0.004(11) C45 0.054(9) 0.27(3) 0.106(13) -0.074(15) 0.004(9) -0.055(13) C46 0.071(9) 0.180(17) 0.069(9) -0.044(10) 0.011(7) -0.067(11) C52 0.045(7) 0.105(11) 0.090(10) -0.072(9) 0.018(7) -0.039(7) C53 0.057(9) 0.168(19) 0.146(16) -0.123(15) 0.049(10) -0.066(11) C54 0.079(12) 0.29(3) 0.079(12) -0.107(17) 0.032(10) -0.111(17) C55 0.092(11) 0.179(18) 0.038(7) -0.032(9) -0.004(7) -0.065(12) C56 0.044(7) 0.119(11) 0.048(7) -0.022(7) 0.005(5) -0.032(7) C62 0.038(7) 0.077(10) 0.131(13) -0.062(10) 0.011(7) -0.027(7) C63 0.064(10) 0.074(12) 0.23(2) -0.087(14) 0.004(12) -0.024(9) C64 0.074(12) 0.059(12) 0.30(3) -0.012(16) -0.075(17) -0.002(9) C65 0.078(10) 0.037(8) 0.21(2) -0.001(10) -0.072(12) -0.003(7) C66 0.061(8) 0.043(7) 0.121(11) 0.004(7) -0.050(8) -0.009(6) C72 0.055(6) 0.027(5) 0.035(5) 0.006(4) 0.007(5) -0.007(5) C73 0.063(7) 0.044(7) 0.046(6) 0.005(5) 0.006(6) 0.002(6) C74 0.049(7) 0.045(7) 0.073(8) 0.020(6) 0.006(6) -0.005(5) C75 0.051(6) 0.042(6) 0.058(7) 0.009(5) -0.010(5) -0.017(5) C76 0.036(5) 0.035(5) 0.055(6) -0.002(5) -0.011(5) -0.005(4) C82 0.064(7) 0.022(5) 0.031(5) 0.007(4) -0.003(5) 0.004(5) C83 0.100(9) 0.024(5) 0.038(6) 0.002(4) -0.014(6) -0.004(6) C84 0.128(12) 0.041(7) 0.030(6) 0.003(5) -0.028(7) -0.004(7) C85 0.113(11) 0.045(7) 0.053(7) 0.003(6) -0.048(8) -0.009(7) C86 0.068(7) 0.037(6) 0.053(6) 0.005(5) -0.030(6) -0.007(5) C92 0.033(5) 0.047(6) 0.033(5) -0.015(4) -0.010(4) -0.003(5) C93 0.026(5) 0.067(8) 0.054(6) -0.023(5) -0.014(4) -0.002(5) C94 0.031(5) 0.054(7) 0.065(7) -0.024(5) -0.005(5) -0.018(5) C95 0.035(5) 0.048(6) 0.039(5) -0.005(4) -0.011(4) -0.016(5) C96 0.022(4) 0.060(7) 0.033(5) 0.003(4) -0.011(4) -0.010(4) C97 0.034(5) 0.044(6) 0.026(5) 0.002(4) -0.011(4) -0.011(4) C102 0.030(5) 0.059(7) 0.082(8) -0.021(6) 0.001(5) -0.022(5) C103 0.031(5) 0.057(7) 0.085(8) -0.024(6) -0.018(5) -0.005(5) C104 0.041(7) 0.070(9) 0.137(13) -0.025(9) -0.036(8) -0.003(7) C105 0.043(7) 0.071(10) 0.153(14) -0.044(10) -0.015(9) -0.020(7) C106 0.057(8) 0.074(9) 0.099(10) -0.009(8) 0.018(7) -0.039(7) C107 0.049(7) 0.075(8) 0.070(8) -0.006(7) 0.002(6) -0.036(6) O98 0.024(3) 0.049(4) 0.039(3) 0.007(3) -0.008(3) -0.011(3) O108 0.083(6) 0.097(7) 0.075(6) 0.026(5) -0.018(5) -0.067(5) O30 0.38(3) 0.24(2) 0.164(14) 0.067(13) -0.120(17) -0.16(2) O31 0.167(14) 0.118(12) 0.54(4) 0.007(16) -0.228(19) -0.048(10) _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 N91 2.002(8) . ? Ru1 N51 2.038(8) . ? Ru1 N61 2.038(9) . ? Ru1 N81 2.051(7) . ? Ru1 N71 2.054(7) . ? Ru1 O98 2.093(6) . ? Ru2 N41 2.025(10) . ? Ru2 N21 2.028(10) . ? Ru2 N31 2.037(7) . ? Ru2 N11 2.059(10) . ? Ru2 O108 2.073(7) . ? Ru2 N101 2.077(8) . ? Cl1 O14 1.299(10) . ? Cl1 O11 1.317(11) . ? Cl1 O13 1.433(8) . ? Cl1 O12 1.434(15) . ? Cl2 O22 1.312(14) . ? Cl2 O21 1.370(14) . ? Cl2 O24 1.442(10) . ? Cl2 O23 1.59(2) . ? N11 C16 1.353(15) . ? N11 C12 1.351(17) . ? N21 C26 1.326(12) . ? N21 C22 1.383(14) . ? N31 C36 1.347(12) . ? N31 C32 1.355(12) . ? N41 C46 1.335(14) . ? N41 C42 1.365(13) . ? N51 C56 1.338(15) . ? N51 C52 1.346(15) . ? N61 C66 1.347(14) . ? N61 C62 1.350(15) . ? N71 C76 1.360(11) . ? N71 C72 1.371(11) . ? N81 C82 1.336(12) . ? N81 C86 1.359(12) . ? N91 C92 1.331(12) . ? N101 C95 1.345(12) . ? N101 C102 1.429(11) . ? C12 C13 1.412(17) . ? C12 C22 1.470(16) . ? C13 C14 1.37(2) . ? C14 C15 1.37(3) . ? C15 C16 1.43(2) . ? C22 C23 1.360(18) . ? C23 C24 1.411(18) . ? C24 C25 1.378(16) . ? C25 C26 1.365(15) . ? C32 C33 1.395(13) . ? C32 C42 1.464(14) . ? C33 C34 1.336(14) . ? C34 C35 1.399(15) . ? C35 C36 1.379(13) . ? C42 C43 1.388(16) . ? C43 C44 1.390(18) . ? C44 C45 1.38(2) . ? C45 C46 1.36(2) . ? C52 C53 1.403(19) . ? C52 C62 1.485(19) . ? C53 C54 1.36(3) . ? C54 C55 1.31(3) . ? C55 C56 1.395(16) . ? C62 C63 1.42(2) . ? C63 C64 1.37(3) . ? C64 C65 1.33(3) . ? C65 C66 1.363(16) . ? C72 C73 1.351(14) . ? C72 C82 1.476(14) . ? C73 C74 1.394(15) . ? C74 C75 1.374(14) . ? C75 C76 1.389(13) . ? C82 C83 1.414(13) . ? C83 C84 1.372(16) . ? C84 C85 1.353(17) . ? C85 C86 1.398(14) . ? C92 C93 1.430(13) . ? C92 C97 1.456(12) . ? C93 C94 1.359(14) . ? C94 C95 1.481(13) . ? C95 C96 1.398(12) . ? C96 C97 1.375(12) . ? C97 O98 1.309(10) . ? C102 C103 1.398(14) . ? C102 C107 1.394(16) . ? C103 C104 1.370(15) . ? C104 C105 1.39(2) . ? C105 C106 1.379(18) . ? C106 C107 1.414(15) . ? C107 O108 1.343(14) . ? 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 N91 Ru1 N51 90.4(3) . . ? N91 Ru1 N61 95.6(3) . . ? N51 Ru1 N61 78.4(4) . . ? N91 Ru1 N81 94.9(3) . . ? N51 Ru1 N81 174.4(3) . . ? N61 Ru1 N81 99.0(3) . . ? N91 Ru1 N71 171.3(3) . . ? N51 Ru1 N71 96.7(3) . . ? N61 Ru1 N71 90.8(3) . . ? N81 Ru1 N71 78.3(3) . . ? N91 Ru1 O98 79.1(3) . . ? N51 Ru1 O98 96.4(3) . . ? N61 Ru1 O98 172.6(3) . . ? N81 Ru1 O98 86.6(3) . . ? N71 Ru1 O98 95.0(2) . . ? N41 Ru2 N21 173.6(3) . . ? N41 Ru2 N31 79.2(3) . . ? N21 Ru2 N31 94.5(3) . . ? N41 Ru2 N11 98.9(4) . . ? N21 Ru2 N11 79.8(4) . . ? N31 Ru2 N11 89.0(3) . . ? N41 Ru2 O108 94.9(4) . . ? N21 Ru2 O108 91.3(3) . . ? N31 Ru2 O108 172.9(3) . . ? N11 Ru2 O108 88.1(3) . . ? N41 Ru2 N101 86.3(3) . . ? N21 Ru2 N101 96.2(3) . . ? N31 Ru2 N101 103.0(3) . . ? N11 Ru2 N101 167.7(3) . . ? O108 Ru2 N101 80.3(3) . . ? O14 Cl1 O11 115.0(10) . . ? O14 Cl1 O13 112.8(7) . . ? O11 Cl1 O13 113.5(8) . . ? O14 Cl1 O12 103.6(14) . . ? O11 Cl1 O12 102.8(14) . . ? O13 Cl1 O12 107.7(8) . . ? O22 Cl2 O21 114.9(14) . . ? O22 Cl2 O24 122.2(11) . . ? O21 Cl2 O24 115.6(8) . . ? O22 Cl2 O23 96.2(17) . . ? O21 Cl2 O23 107(2) . . ? O24 Cl2 O23 94.6(18) . . ? C16 N11 C12 121.2(12) . . ? C16 N11 Ru2 124.3(11) . . ? C12 N11 Ru2 114.3(7) . . ? C26 N21 C22 116.7(10) . . ? C26 N21 Ru2 127.0(7) . . ? C22 N21 Ru2 115.9(8) . . ? C36 N31 C32 117.7(8) . . ? C36 N31 Ru2 125.9(7) . . ? C32 N31 Ru2 116.4(6) . . ? C46 N41 C42 119.9(11) . . ? C46 N41 Ru2 124.6(9) . . ? C42 N41 Ru2 115.1(7) . . ? C56 N51 C52 118.5(11) . . ? C56 N51 Ru1 124.0(8) . . ? C52 N51 Ru1 117.4(9) . . ? C66 N61 C62 119.4(12) . . ? C66 N61 Ru1 124.5(8) . . ? C62 N61 Ru1 116.1(10) . . ? C76 N71 C72 117.8(8) . . ? C76 N71 Ru1 126.2(6) . . ? C72 N71 Ru1 116.0(6) . . ? C82 N81 C86 118.9(9) . . ? C82 N81 Ru1 116.8(6) . . ? C86 N81 Ru1 124.0(7) . . ? C92 N91 Ru1 116.3(6) . . ? C95 N101 C102 120.5(8) . . ? C95 N101 Ru2 127.6(6) . . ? C102 N101 Ru2 110.1(7) . . ? N11 C12 C13 121.4(13) . . ? N11 C12 C22 116.3(11) . . ? C13 C12 C22 122.2(15) . . ? C14 C13 C12 118.6(17) . . ? C15 C14 C13 119.6(16) . . ? C14 C15 C16 121.4(16) . . ? N11 C16 C15 117.8(17) . . ? C23 C22 N21 121.8(11) . . ? C23 C22 C12 125.0(12) . . ? N21 C22 C12 113.2(12) . . ? C22 C23 C24 120.0(12) . . ? C25 C24 C23 117.5(12) . . ? C26 C25 C24 119.1(12) . . ? N21 C26 C25 124.8(10) . . ? N31 C32 C33 122.3(9) . . ? N31 C32 C42 113.4(9) . . ? C33 C32 C42 124.3(10) . . ? C34 C33 C32 118.8(10) . . ? C33 C34 C35 120.7(10) . . ? C36 C35 C34 117.8(10) . . ? N31 C36 C35 122.7(10) . . ? N41 C42 C43 120.1(11) . . ? N41 C42 C32 115.3(10) . . ? C43 C42 C32 124.6(11) . . ? C44 C43 C42 118.5(14) . . ? C45 C44 C43 120.3(14) . . ? C46 C45 C44 118.5(13) . . ? N41 C46 C45 122.7(14) . . ? N51 C52 C53 119.4(17) . . ? N51 C52 C62 112.9(10) . . ? C53 C52 C62 127.7(16) . . ? C54 C53 C52 121.9(19) . . ? C55 C54 C53 116.6(15) . . ? C54 C55 C56 122.9(18) . . ? N51 C56 C55 120.5(14) . . ? N61 C62 C63 118.0(17) . . ? N61 C62 C52 114.9(11) . . ? C63 C62 C52 127.2(15) . . ? C64 C63 C62 120.6(18) . . ? C65 C64 C63 119.7(18) . . ? C64 C65 C66 119.5(18) . . ? N61 C66 C65 122.8(14) . . ? C73 C72 N71 122.7(10) . . ? C73 C72 C82 123.5(9) . . ? N71 C72 C82 113.7(8) . . ? C72 C73 C74 119.0(10) . . ? C75 C74 C73 119.8(10) . . ? C74 C75 C76 118.8(10) . . ? N71 C76 C75 121.8(9) . . ? N81 C82 C83 122.2(10) . . ? N81 C82 C72 114.7(8) . . ? C83 C82 C72 123.1(10) . . ? C84 C83 C82 117.8(11) . . ? C85 C84 C83 120.5(11) . . ? C84 C85 C86 119.8(12) . . ? N81 C86 C85 120.8(11) . . ? N91 C92 C93 125.8(9) . . ? N91 C92 C97 114.1(8) . . ? C93 C92 C97 120.1(9) . . ? C94 C93 C92 120.8(9) . . ? C93 C94 C95 119.9(8) . . ? N101 C95 C96 121.9(8) . . ? N101 C95 C94 120.0(8) . . ? C96 C95 C94 117.8(9) . . ? C97 C96 C95 123.8(8) . . ? O98 C97 C96 124.7(8) . . ? O98 C97 C92 117.7(8) . . ? C96 C97 C92 117.6(8) . . ? C103 C102 C107 120.7(10) . . ? C103 C102 N101 123.5(10) . . ? C107 C102 N101 115.5(10) . . ? C104 C103 C102 120.2(12) . . ? C103 C104 C105 119.6(13) . . ? C106 C105 C104 121.0(12) . . ? C105 C106 C107 120.0(12) . . ? O108 C107 C102 119.5(9) . . ? O108 C107 C106 122.8(11) . . ? C102 C107 C106 117.7(12) . . ? C97 O98 Ru1 112.0(5) . . ? C107 O108 Ru2 111.8(6) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.502 _refine_diff_density_min -1.430 _refine_diff_density_rms 0.143 #CIF file for H2L1 #Title : H2L1 data_'C10 H8 N O' _database_code_CSD 164246 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'diimine' _chemical_formula_moiety '(OH)C6H4-N=CH-C6H4-CH=N-H4C6(OH)' _chemical_formula_sum 'C10 H8 N O' _chemical_formula_weight 158.17 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 8.5030(15) _cell_length_b 6.008(4) _cell_length_c 15.527(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.090(10) _cell_angle_gamma 90.00 _cell_volume 792.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 6 _cell_measurement_theta_max 12 _exptl_crystal_description 'needle' _exptl_crystal_colour 'yellow' _exptl_crystal_size_max '0.4' _exptl_crystal_size_mid '0.085' _exptl_crystal_size_min '0.057' _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.325 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 332 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.70930 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Enraf-Nonius CAD-4' _diffrn_measurement_method '\w/2\q-scan' _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 3600 _diffrn_standards_decay_% '<4%' _diffrn_reflns_number 1399 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1334 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 24.98 _reflns_number_total 1399 _reflns_number_gt 580 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1989)' _computing_cell_refinement 'CAD-4 Software' _computing_data_reduction 'NRCVAX (PC Version) Gabe, E. J. et al., 1989)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ZORTEP (Zsolnai, L and Pritzkow, H, 1994)' _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^ > 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 w=1/[\s^2^(Fo^2^)+(0.2000P)^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 1399 _refine_ls_number_parameters 141 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1707 _refine_ls_R_factor_gt 0.0574 _refine_ls_wR_factor_ref 0.2283 _refine_ls_wR_factor_gt 0.1708 _refine_ls_goodness_of_fit_ref 0.641 _refine_ls_restrained_S_all 0.641 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.001 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C6 C 0.5489(4) 0.0763(7) 0.1363(2) 0.0442(11) Uani 1 d . . . C5 C 0.5994(6) -0.0900(9) 0.1918(3) 0.0637(14) Uani 1 d . . . C4 C 0.7436(6) -0.0727(9) 0.2344(3) 0.0691(15) Uani 1 d . . . C2 C 0.7926(5) 0.2748(9) 0.1654(3) 0.0661(14) Uani 1 d . . . C1 C 0.6476(5) 0.2574(7) 0.1236(3) 0.0519(12) Uani 1 d . . . C3 C 0.8392(6) 0.1068(10) 0.2203(3) 0.0694(15) Uani 1 d . . . C7 C 0.2992(5) -0.0555(8) 0.0876(3) 0.0499(12) Uani 1 d . . . C8 C 0.1479(5) -0.0246(7) 0.0423(3) 0.0475(11) Uani 1 d . . . C9 C 0.1094(5) 0.1669(8) -0.0031(3) 0.0549(13) Uani 1 d . . . O1 O 0.5994(4) 0.4235(5) 0.0680(2) 0.0820(13) Uani 1 d . . . N N 0.4036(4) 0.0968(6) 0.0894(2) 0.0501(10) Uani 1 d . . . C10 C 0.0337(5) -0.1935(7) 0.0432(3) 0.0535(12) Uani 1 d . . . H9 H 0.189(4) 0.270(6) -0.005(2) 0.042(10) Uiso 1 d . . . H3 H 0.945(6) 0.122(9) 0.250(3) 0.101(17) Uiso 1 d . . . H7 H 0.298(4) -0.193(7) 0.125(3) 0.067(13) Uiso 1 d . . . H10 H 0.058(5) -0.320(8) 0.077(3) 0.079(15) Uiso 1 d . . . H4 H 0.785(5) -0.162(8) 0.275(3) 0.082(16) Uiso 1 d . . . H5 H 0.539(6) -0.221(10) 0.206(3) 0.097(18) Uiso 1 d . . . H2 H 0.861(5) 0.394(8) 0.151(3) 0.081(15) Uiso 1 d . . . H H 0.503(6) 0.373(8) 0.045(3) 0.086(16) Uiso 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 C6 0.040(2) 0.048(3) 0.045(2) -0.001(2) 0.0014(18) -0.0027(19) C5 0.068(3) 0.056(3) 0.068(3) 0.014(3) 0.004(3) -0.001(3) C4 0.068(3) 0.074(4) 0.064(3) 0.016(3) -0.013(3) 0.010(3) C2 0.063(3) 0.072(3) 0.063(3) 0.010(3) -0.010(2) -0.024(3) C1 0.053(2) 0.051(3) 0.051(3) 0.002(2) -0.006(2) -0.009(2) C3 0.059(3) 0.083(4) 0.065(3) 0.002(3) -0.013(2) -0.009(3) C7 0.049(3) 0.043(3) 0.058(3) -0.001(2) 0.003(2) -0.009(2) C8 0.045(2) 0.044(2) 0.055(3) -0.005(2) 0.0079(19) -0.005(2) C9 0.043(3) 0.054(3) 0.067(3) -0.003(2) 0.003(2) -0.021(2) O1 0.076(2) 0.067(2) 0.100(3) 0.031(2) -0.034(2) -0.030(2) N 0.046(2) 0.048(2) 0.056(2) -0.0025(18) 0.0017(17) -0.0059(17) C10 0.051(3) 0.041(3) 0.068(3) 0.007(2) 0.005(2) -0.008(2) _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 C6 C5 1.378(6) . ? C6 C1 1.392(6) . ? C6 N 1.418(5) . ? C5 C4 1.375(6) . ? C4 C3 1.373(7) . ? C2 C3 1.371(7) . ? C2 C1 1.377(6) . ? C1 O1 1.372(5) . ? C7 N 1.274(5) . ? C7 C8 1.457(6) . ? C8 C9 1.382(6) . ? C8 C10 1.405(6) . ? C9 C10 1.356(6) 3 ? C10 C9 1.356(6) 3 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 C6 C1 118.7(4) . . ? C5 C6 N 129.1(4) . . ? C1 C6 N 112.2(4) . . ? C4 C5 C6 119.9(5) . . ? C3 C4 C5 120.4(5) . . ? C3 C2 C1 118.1(5) . . ? O1 C1 C2 118.9(4) . . ? O1 C1 C6 119.3(3) . . ? C2 C1 C6 121.8(4) . . ? C2 C3 C4 121.2(5) . . ? N C7 C8 121.4(4) . . ? C9 C8 C10 117.1(4) . . ? C9 C8 C7 122.8(4) . . ? C10 C8 C7 120.1(4) . . ? C10 C9 C8 121.6(4) 3 . ? C7 N C6 122.8(4) . . ? C9 C10 C8 121.3(4) 3 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 C6 C5 C4 1.1(7) . . . . ? N C6 C5 C4 -176.9(4) . . . . ? C6 C5 C4 C3 -1.6(8) . . . . ? C3 C2 C1 O1 -179.7(4) . . . . ? C3 C2 C1 C6 0.4(7) . . . . ? C5 C6 C1 O1 179.5(4) . . . . ? N C6 C1 O1 -2.1(6) . . . . ? C5 C6 C1 C2 -0.6(6) . . . . ? N C6 C1 C2 177.8(4) . . . . ? C1 C2 C3 C4 -0.9(8) . . . . ? C5 C4 C3 C2 1.5(8) . . . . ? N C7 C8 C9 1.7(6) . . . . ? N C7 C8 C10 -178.5(4) . . . . ? C10 C8 C9 C10 1.7(7) . . . 3 ? C7 C8 C9 C10 -178.5(4) . . . 3 ? C8 C7 N C6 176.9(4) . . . . ? C5 C6 N C7 -5.9(7) . . . . ? C1 C6 N C7 175.9(4) . . . . ? C9 C8 C10 C9 -1.7(7) . . . 3 ? C7 C8 C10 C9 178.5(4) . . . 3 ? _diffrn_measured_fraction_theta_max 0.902 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.902 _refine_diff_density_max 0.134 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.042