Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 182 _publ_contact_author_name 'Prof Hideo Nagashima' _publ_contact_author_phone '81-92-583-7819' _publ_contact_author_fax '81-92-583-7819' _publ_contact_author_email 'nagasima@cm.kyushu-u.ac.jp' _publ_contact_author_address ; Institute of Advanced Material Study Kyushu University Kasuga-koen 6-1 Kasuga Fukuoka 816-8580 JAPAN ; _publ_requested_journal 'Chemical Communications' _publ_section_title ; Organoruthenium (II) and (III) Amidinates, (h5-C5Me5)Ru(h-amidinate) and (h5-C5Me5)RuCl(h-amidinate), as Unique Redox Catalysts for Intramolecular Kharash Reactions: Facile Access to Pyrrolitizine Alkaroid Sleletons Under Mild Conditions ; loop_ _publ_author_name 'Hideo Nagashima' 'Mitsuru Gondo' 'Satoshi Masuda' 'Hideo Kondo' 'Yoshitaka Yamaguchi' 'Kouki Matsubara' data_2 _database_code_CSD 194483 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H32 Cl N2 Ru' _chemical_formula_weight 412.98 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' '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 monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.149(2) _cell_length_b 9.255(3) _cell_length_c 16.412(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.473(14) _cell_angle_gamma 90.00 _cell_volume 1997.2(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 14.66 _cell_measurement_theta_max 14.85 _exptl_crystal_description prismatic _exptl_crystal_colour orange _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.230 _exptl_crystal_size_min 0.100 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.373 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 860 _exptl_absorpt_coefficient_mu 0.918 _exptl_absorpt_correction_type 'psi scan' _exptl_absorpt_correction_T_min 0.930 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device 'Rigaku AFC7R' _diffrn_measurement_method \w-2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 5.619 _diffrn_reflns_number 4728 _diffrn_reflns_av_R_equivalents 0.0509 _diffrn_reflns_av_sigmaI/netI 0.1137 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 2.53 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4573 _reflns_number_gt 2343 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction ; teXsan for Windows version 1.06 (MSC, 1997-1999) ; _computing_structure_solution ; SIR97 (Altomare, et. al. 1997) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97/2 (Sheldrick,1997)' _computing_molecular_graphics 'ORTEP III (Farrujia, 1998)' _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^)+(0.0420P)^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 4573 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1410 _refine_ls_R_factor_gt 0.0399 _refine_ls_wR_factor_ref 0.1159 _refine_ls_wR_factor_gt 0.0924 _refine_ls_goodness_of_fit_ref 0.970 _refine_ls_restrained_S_all 0.970 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ru1 Ru 0.73379(3) 0.24009(4) 0.45264(2) 0.03473(12) Uani 1 1 d . . . Cl1 Cl 0.73735(12) -0.00486(15) 0.40671(11) 0.0645(5) Uani 1 1 d . . . N1 N 0.8310(3) 0.1901(5) 0.5505(3) 0.0429(10) Uani 1 1 d . . . N2 N 0.8905(3) 0.2625(5) 0.4372(3) 0.0465(10) Uani 1 1 d . . . C1 C 0.5695(4) 0.2697(5) 0.4260(3) 0.0443(12) Uani 1 1 d . . . C2 C 0.5944(4) 0.3292(6) 0.5035(3) 0.0471(13) Uani 1 1 d . . . C3 C 0.6658(4) 0.4433(6) 0.4911(3) 0.0471(14) Uani 1 1 d . . . C4 C 0.6832(4) 0.4539(5) 0.4048(3) 0.0427(12) Uani 1 1 d . . . C5 C 0.6252(4) 0.3452(6) 0.3662(3) 0.0441(13) Uani 1 1 d . . . C6 C 0.4956(5) 0.1503(7) 0.4094(4) 0.0683(19) Uani 1 1 d . . . H6A H 0.4681 0.1163 0.4599 0.102 Uiso 1 1 calc . . . H6B H 0.5297 0.0725 0.3823 0.102 Uiso 1 1 calc . . . H6C H 0.4414 0.1857 0.3753 0.102 Uiso 1 1 calc . . . C7 C 0.5422(5) 0.2955(8) 0.5823(4) 0.077(2) Uani 1 1 d . . . H7A H 0.5733 0.3500 0.6256 0.116 Uiso 1 1 calc . . . H7B H 0.5485 0.1941 0.5938 0.116 Uiso 1 1 calc . . . H7C H 0.4716 0.3207 0.5778 0.116 Uiso 1 1 calc . . . C8 C 0.7052(6) 0.5467(7) 0.5531(4) 0.080(2) Uani 1 1 d . . . H8A H 0.6846 0.5159 0.6064 0.121 Uiso 1 1 calc . . . H8B H 0.6783 0.6412 0.5423 0.121 Uiso 1 1 calc . . . H8C H 0.7781 0.5496 0.5508 0.121 Uiso 1 1 calc . . . C9 C 0.7464(5) 0.5678(7) 0.3644(5) 0.073(2) Uani 1 1 d . . . H9A H 0.7781 0.6273 0.4052 0.110 Uiso 1 1 calc . . . H9B H 0.7036 0.6265 0.3301 0.110 Uiso 1 1 calc . . . H9C H 0.7977 0.5225 0.3319 0.110 Uiso 1 1 calc . . . C10 C 0.6165(5) 0.3190(8) 0.2756(4) 0.0686(18) Uani 1 1 d . . . H10A H 0.6614 0.3832 0.2474 0.103 Uiso 1 1 calc . . . H10B H 0.5477 0.3365 0.2580 0.103 Uiso 1 1 calc . . . H10C H 0.6346 0.2208 0.2638 0.103 Uiso 1 1 calc . . . C11 C 0.9144(4) 0.2122(5) 0.5099(3) 0.0434(13) Uani 1 1 d . . . C12 C 0.8282(5) 0.1225(7) 0.6310(4) 0.0575(16) Uani 1 1 d . . . H12 H 0.8950 0.0786 0.6407 0.069 Uiso 1 1 calc . . . C13 C 0.8115(6) 0.2305(8) 0.6970(4) 0.083(2) Uani 1 1 d . . . H13A H 0.8640 0.3025 0.6953 0.125 Uiso 1 1 calc . . . H13B H 0.8133 0.1827 0.7489 0.125 Uiso 1 1 calc . . . H13C H 0.7465 0.2758 0.6893 0.125 Uiso 1 1 calc . . . C14 C 0.7515(6) 0.0034(8) 0.6315(5) 0.094(3) Uani 1 1 d . . . H14A H 0.7657 -0.0631 0.5881 0.141 Uiso 1 1 calc . . . H14B H 0.6847 0.0431 0.6239 0.141 Uiso 1 1 calc . . . H14C H 0.7549 -0.0465 0.6827 0.141 Uiso 1 1 calc . . . C15 C 0.9636(5) 0.2768(7) 0.3712(4) 0.0633(17) Uani 1 1 d . . . H15 H 1.0175 0.2059 0.3817 0.076 Uiso 1 1 calc . . . C16 C 1.0143(5) 0.4243(9) 0.3697(5) 0.093(3) Uani 1 1 d . . . H16A H 1.0457 0.4430 0.4217 0.139 Uiso 1 1 calc . . . H16B H 0.9642 0.4972 0.3585 0.139 Uiso 1 1 calc . . . H16C H 1.0651 0.4260 0.3280 0.139 Uiso 1 1 calc . . . C17 C 0.9165(7) 0.2374(10) 0.2929(5) 0.115(3) Uani 1 1 d . . . H17A H 0.8845 0.1445 0.2977 0.172 Uiso 1 1 calc . . . H17B H 0.9677 0.2334 0.2516 0.172 Uiso 1 1 calc . . . H17C H 0.8664 0.3084 0.2783 0.172 Uiso 1 1 calc . . . C18 C 1.0209(5) 0.1867(7) 0.5413(4) 0.0689(19) Uani 1 1 d . . . H18A H 1.0688 0.2120 0.4999 0.103 Uiso 1 1 calc . . . H18B H 1.0289 0.0866 0.5553 0.103 Uiso 1 1 calc . . . H18C H 1.0327 0.2452 0.5888 0.103 Uiso 1 1 calc . . . 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 0.03362(18) 0.0341(2) 0.03639(19) -0.0014(2) -0.00220(13) 0.0030(2) Cl1 0.0626(10) 0.0419(8) 0.0887(12) -0.0209(8) -0.0173(8) 0.0089(7) N1 0.046(3) 0.040(2) 0.043(3) 0.000(2) -0.008(2) 0.003(2) N2 0.039(2) 0.050(3) 0.050(2) -0.011(3) 0.0025(18) 0.004(2) C1 0.033(2) 0.038(3) 0.061(3) 0.002(3) -0.005(2) 0.004(2) C2 0.041(3) 0.055(3) 0.046(3) 0.005(3) 0.008(2) 0.013(3) C3 0.047(3) 0.040(3) 0.054(3) -0.011(3) -0.012(3) 0.012(2) C4 0.039(3) 0.032(3) 0.057(3) 0.002(2) -0.008(3) 0.000(2) C5 0.043(3) 0.046(3) 0.044(3) 0.005(3) -0.004(2) 0.006(2) C6 0.052(4) 0.056(4) 0.097(5) 0.002(4) -0.017(4) -0.011(3) C7 0.069(4) 0.101(6) 0.062(4) 0.016(4) 0.019(3) 0.031(4) C8 0.090(5) 0.062(4) 0.088(5) -0.037(4) -0.026(4) 0.015(4) C9 0.058(4) 0.048(4) 0.114(6) 0.020(4) 0.002(4) -0.006(3) C10 0.070(4) 0.079(5) 0.056(4) 0.002(4) -0.012(3) 0.007(4) C11 0.041(3) 0.036(3) 0.053(3) -0.008(2) -0.012(2) 0.006(2) C12 0.059(4) 0.063(4) 0.051(4) 0.011(3) -0.012(3) -0.002(3) C13 0.107(6) 0.100(6) 0.042(3) -0.001(4) -0.010(3) -0.011(5) C14 0.113(7) 0.083(5) 0.085(6) 0.020(5) -0.002(5) -0.036(5) C15 0.052(3) 0.070(4) 0.068(4) -0.005(3) 0.020(3) -0.007(3) C16 0.070(5) 0.095(6) 0.114(7) 0.007(5) 0.022(5) -0.028(4) C17 0.121(7) 0.160(9) 0.064(4) -0.039(6) 0.036(4) -0.064(7) C18 0.043(3) 0.074(4) 0.089(5) -0.015(4) -0.022(3) 0.000(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 Ru1 N2 2.088(4) . ? Ru1 N1 2.096(4) . ? Ru1 C3 2.178(5) . ? Ru1 C2 2.182(5) . ? Ru1 C1 2.217(5) . ? Ru1 C5 2.228(5) . ? Ru1 C4 2.228(5) . ? Ru1 Cl1 2.3896(16) . ? Ru1 C11 2.560(5) . ? N1 C11 1.305(7) . ? N1 C12 1.461(7) . ? N2 C11 1.316(7) . ? N2 C15 1.462(7) . ? C1 C5 1.415(7) . ? C1 C2 1.421(7) . ? C1 C6 1.495(7) . ? C2 C3 1.429(7) . ? C2 C7 1.501(8) . ? C3 C4 1.439(7) . ? C3 C8 1.487(8) . ? C4 C5 1.410(7) . ? C4 C9 1.500(7) . ? C5 C10 1.510(8) . ? C11 C18 1.507(7) . ? C12 C13 1.492(8) . ? C12 C14 1.494(9) . ? C15 C17 1.467(10) . ? C15 C16 1.520(9) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Ru1 N1 61.23(17) . . ? N2 Ru1 C3 110.92(19) . . ? N1 Ru1 C3 102.58(18) . . ? N2 Ru1 C2 147.3(2) . . ? N1 Ru1 C2 107.39(19) . . ? C3 Ru1 C2 38.3(2) . . ? N2 Ru1 C1 157.60(18) . . ? N1 Ru1 C1 139.90(19) . . ? C3 Ru1 C1 63.18(19) . . ? C2 Ru1 C1 37.69(19) . . ? N2 Ru1 C5 120.47(19) . . ? N1 Ru1 C5 165.43(18) . . ? C3 Ru1 C5 62.9(2) . . ? C2 Ru1 C5 62.8(2) . . ? C1 Ru1 C5 37.13(18) . . ? N2 Ru1 C4 99.28(18) . . ? N1 Ru1 C4 130.11(18) . . ? C3 Ru1 C4 38.10(19) . . ? C2 Ru1 C4 63.2(2) . . ? C1 Ru1 C4 62.18(19) . . ? C5 Ru1 C4 36.88(18) . . ? N2 Ru1 Cl1 91.95(13) . . ? N1 Ru1 Cl1 91.09(12) . . ? C3 Ru1 Cl1 156.90(15) . . ? C2 Ru1 Cl1 119.87(16) . . ? C1 Ru1 Cl1 94.40(14) . . ? C5 Ru1 Cl1 103.14(15) . . ? C4 Ru1 Cl1 137.55(14) . . ? N2 Ru1 C11 30.81(17) . . ? N1 Ru1 C11 30.52(16) . . ? C3 Ru1 C11 111.25(18) . . ? C2 Ru1 C11 132.63(19) . . ? C1 Ru1 C11 169.77(19) . . ? C5 Ru1 C11 149.92(19) . . ? C4 Ru1 C11 119.49(17) . . ? Cl1 Ru1 C11 89.98(11) . . ? C11 N1 C12 123.8(5) . . ? C11 N1 Ru1 94.8(3) . . ? C12 N1 Ru1 140.1(4) . . ? C11 N2 C15 123.4(5) . . ? C11 N2 Ru1 94.8(3) . . ? C15 N2 Ru1 139.0(4) . . ? C5 C1 C2 108.2(5) . . ? C5 C1 C6 125.3(5) . . ? C2 C1 C6 126.5(5) . . ? C5 C1 Ru1 71.8(3) . . ? C2 C1 Ru1 69.8(3) . . ? C6 C1 Ru1 125.2(4) . . ? C1 C2 C3 107.8(5) . . ? C1 C2 C7 125.9(6) . . ? C3 C2 C7 125.6(6) . . ? C1 C2 Ru1 72.5(3) . . ? C3 C2 Ru1 70.7(3) . . ? C7 C2 Ru1 129.9(4) . . ? C2 C3 C4 107.5(5) . . ? C2 C3 C8 127.1(6) . . ? C4 C3 C8 125.0(6) . . ? C2 C3 Ru1 71.0(3) . . ? C4 C3 Ru1 72.8(3) . . ? C8 C3 Ru1 127.7(4) . . ? C5 C4 C3 107.7(5) . . ? C5 C4 C9 127.0(5) . . ? C3 C4 C9 125.2(5) . . ? C5 C4 Ru1 71.5(3) . . ? C3 C4 Ru1 69.1(3) . . ? C9 C4 Ru1 127.9(4) . . ? C4 C5 C1 108.7(5) . . ? C4 C5 C10 126.5(5) . . ? C1 C5 C10 124.7(5) . . ? C4 C5 Ru1 71.6(3) . . ? C1 C5 Ru1 71.0(3) . . ? C10 C5 Ru1 126.9(4) . . ? N1 C11 N2 108.8(5) . . ? N1 C11 C18 125.7(5) . . ? N2 C11 C18 125.5(5) . . ? N1 C11 Ru1 54.7(3) . . ? N2 C11 Ru1 54.4(3) . . ? C18 C11 Ru1 176.5(4) . . ? N1 C12 C13 112.0(5) . . ? N1 C12 C14 110.1(5) . . ? C13 C12 C14 112.8(6) . . ? N2 C15 C17 110.5(5) . . ? N2 C15 C16 112.6(6) . . ? C17 C15 C16 113.1(7) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 Ru1 N1 C11 -3.5(3) . . . . ? C3 Ru1 N1 C11 -110.7(3) . . . . ? C2 Ru1 N1 C11 -150.0(3) . . . . ? C1 Ru1 N1 C11 -173.7(3) . . . . ? C5 Ru1 N1 C11 -104.3(8) . . . . ? C4 Ru1 N1 C11 -80.7(4) . . . . ? Cl1 Ru1 N1 C11 88.1(3) . . . . ? N2 Ru1 N1 C12 -169.5(6) . . . . ? C3 Ru1 N1 C12 83.4(6) . . . . ? C2 Ru1 N1 C12 44.0(6) . . . . ? C1 Ru1 N1 C12 20.3(7) . . . . ? C5 Ru1 N1 C12 89.7(9) . . . . ? C4 Ru1 N1 C12 113.3(6) . . . . ? Cl1 Ru1 N1 C12 -77.9(6) . . . . ? C11 Ru1 N1 C12 -166.0(8) . . . . ? N1 Ru1 N2 C11 3.5(3) . . . . ? C3 Ru1 N2 C11 96.7(3) . . . . ? C2 Ru1 N2 C11 80.5(5) . . . . ? C1 Ru1 N2 C11 166.8(4) . . . . ? C5 Ru1 N2 C11 166.8(3) . . . . ? C4 Ru1 N2 C11 134.4(3) . . . . ? Cl1 Ru1 N2 C11 -86.7(3) . . . . ? N1 Ru1 N2 C15 163.4(6) . . . . ? C3 Ru1 N2 C15 -103.3(6) . . . . ? C2 Ru1 N2 C15 -119.5(6) . . . . ? C1 Ru1 N2 C15 -33.2(9) . . . . ? C5 Ru1 N2 C15 -33.2(6) . . . . ? C4 Ru1 N2 C15 -65.6(6) . . . . ? Cl1 Ru1 N2 C15 73.3(6) . . . . ? C11 Ru1 N2 C15 160.0(8) . . . . ? N2 Ru1 C1 C5 0.0(6) . . . . ? N1 Ru1 C1 C5 157.0(3) . . . . ? C3 Ru1 C1 C5 79.8(3) . . . . ? C2 Ru1 C1 C5 118.1(5) . . . . ? C4 Ru1 C1 C5 36.7(3) . . . . ? Cl1 Ru1 C1 C5 -106.0(3) . . . . ? C11 Ru1 C1 C5 138.9(9) . . . . ? N2 Ru1 C1 C2 -118.1(5) . . . . ? N1 Ru1 C1 C2 38.9(4) . . . . ? C3 Ru1 C1 C2 -38.3(3) . . . . ? C5 Ru1 C1 C2 -118.1(5) . . . . ? C4 Ru1 C1 C2 -81.4(3) . . . . ? Cl1 Ru1 C1 C2 135.8(3) . . . . ? C11 Ru1 C1 C2 20.7(11) . . . . ? N2 Ru1 C1 C6 120.8(6) . . . . ? N1 Ru1 C1 C6 -82.1(6) . . . . ? C3 Ru1 C1 C6 -159.3(6) . . . . ? C2 Ru1 C1 C6 -121.0(6) . . . . ? C5 Ru1 C1 C6 120.8(7) . . . . ? C4 Ru1 C1 C6 157.6(6) . . . . ? Cl1 Ru1 C1 C6 14.8(5) . . . . ? C11 Ru1 C1 C6 -100.3(11) . . . . ? C5 C1 C2 C3 0.4(6) . . . . ? C6 C1 C2 C3 -178.3(5) . . . . ? Ru1 C1 C2 C3 62.3(4) . . . . ? C5 C1 C2 C7 171.0(5) . . . . ? C6 C1 C2 C7 -7.7(9) . . . . ? Ru1 C1 C2 C7 -127.1(6) . . . . ? C5 C1 C2 Ru1 -61.9(4) . . . . ? C6 C1 C2 Ru1 119.4(5) . . . . ? N2 Ru1 C2 C1 141.5(3) . . . . ? N1 Ru1 C2 C1 -154.9(3) . . . . ? C3 Ru1 C2 C1 116.7(5) . . . . ? C5 Ru1 C2 C1 36.8(3) . . . . ? C4 Ru1 C2 C1 78.3(3) . . . . ? Cl1 Ru1 C2 C1 -53.2(3) . . . . ? C11 Ru1 C2 C1 -175.1(3) . . . . ? N2 Ru1 C2 C3 24.8(5) . . . . ? N1 Ru1 C2 C3 88.4(3) . . . . ? C1 Ru1 C2 C3 -116.7(5) . . . . ? C5 Ru1 C2 C3 -80.0(3) . . . . ? C4 Ru1 C2 C3 -38.4(3) . . . . ? Cl1 Ru1 C2 C3 -169.9(3) . . . . ? C11 Ru1 C2 C3 68.2(4) . . . . ? N2 Ru1 C2 C7 -95.9(7) . . . . ? N1 Ru1 C2 C7 -32.4(6) . . . . ? C3 Ru1 C2 C7 -120.8(7) . . . . ? C1 Ru1 C2 C7 122.5(7) . . . . ? C5 Ru1 C2 C7 159.3(7) . . . . ? C4 Ru1 C2 C7 -159.2(7) . . . . ? Cl1 Ru1 C2 C7 69.3(6) . . . . ? C11 Ru1 C2 C7 -52.6(7) . . . . ? C1 C2 C3 C4 0.7(6) . . . . ? C7 C2 C3 C4 -169.9(5) . . . . ? Ru1 C2 C3 C4 64.2(4) . . . . ? C1 C2 C3 C8 173.1(5) . . . . ? C7 C2 C3 C8 2.4(9) . . . . ? Ru1 C2 C3 C8 -123.5(6) . . . . ? C1 C2 C3 Ru1 -63.5(4) . . . . ? C7 C2 C3 Ru1 125.9(6) . . . . ? N2 Ru1 C3 C2 -165.9(3) . . . . ? N1 Ru1 C3 C2 -102.2(3) . . . . ? C1 Ru1 C3 C2 37.7(3) . . . . ? C5 Ru1 C3 C2 79.6(3) . . . . ? C4 Ru1 C3 C2 116.0(4) . . . . ? Cl1 Ru1 C3 C2 22.7(6) . . . . ? C11 Ru1 C3 C2 -132.9(3) . . . . ? N2 Ru1 C3 C4 78.0(3) . . . . ? N1 Ru1 C3 C4 141.8(3) . . . . ? C2 Ru1 C3 C4 -116.0(4) . . . . ? C1 Ru1 C3 C4 -78.3(3) . . . . ? C5 Ru1 C3 C4 -36.5(3) . . . . ? Cl1 Ru1 C3 C4 -93.3(5) . . . . ? C11 Ru1 C3 C4 111.1(3) . . . . ? N2 Ru1 C3 C8 -43.3(6) . . . . ? N1 Ru1 C3 C8 20.5(6) . . . . ? C2 Ru1 C3 C8 122.7(7) . . . . ? C1 Ru1 C3 C8 160.4(7) . . . . ? C5 Ru1 C3 C8 -157.7(7) . . . . ? C4 Ru1 C3 C8 -121.3(7) . . . . ? Cl1 Ru1 C3 C8 145.4(5) . . . . ? C11 Ru1 C3 C8 -10.2(6) . . . . ? C2 C3 C4 C5 -1.6(6) . . . . ? C8 C3 C4 C5 -174.1(5) . . . . ? Ru1 C3 C4 C5 61.4(4) . . . . ? C2 C3 C4 C9 174.6(5) . . . . ? C8 C3 C4 C9 2.1(9) . . . . ? Ru1 C3 C4 C9 -122.4(5) . . . . ? C2 C3 C4 Ru1 -63.0(4) . . . . ? C8 C3 C4 Ru1 124.5(6) . . . . ? N2 Ru1 C4 C5 129.7(3) . . . . ? N1 Ru1 C4 C5 -170.3(3) . . . . ? C3 Ru1 C4 C5 -118.1(5) . . . . ? C2 Ru1 C4 C5 -79.6(3) . . . . ? C1 Ru1 C4 C5 -37.0(3) . . . . ? Cl1 Ru1 C4 C5 26.4(4) . . . . ? C11 Ru1 C4 C5 154.5(3) . . . . ? N2 Ru1 C4 C3 -112.2(3) . . . . ? N1 Ru1 C4 C3 -52.2(4) . . . . ? C2 Ru1 C4 C3 38.5(3) . . . . ? C1 Ru1 C4 C3 81.2(3) . . . . ? C5 Ru1 C4 C3 118.1(5) . . . . ? Cl1 Ru1 C4 C3 144.5(3) . . . . ? C11 Ru1 C4 C3 -87.3(3) . . . . ? N2 Ru1 C4 C9 6.7(6) . . . . ? N1 Ru1 C4 C9 66.7(6) . . . . ? C3 Ru1 C4 C9 118.9(7) . . . . ? C2 Ru1 C4 C9 157.5(6) . . . . ? C1 Ru1 C4 C9 -159.9(6) . . . . ? C5 Ru1 C4 C9 -123.0(7) . . . . ? Cl1 Ru1 C4 C9 -96.6(5) . . . . ? C11 Ru1 C4 C9 31.6(6) . . . . ? C3 C4 C5 C1 1.8(6) . . . . ? C9 C4 C5 C1 -174.3(5) . . . . ? Ru1 C4 C5 C1 61.7(4) . . . . ? C3 C4 C5 C10 177.4(5) . . . . ? C9 C4 C5 C10 1.3(9) . . . . ? Ru1 C4 C5 C10 -122.8(6) . . . . ? C3 C4 C5 Ru1 -59.8(3) . . . . ? C9 C4 C5 Ru1 124.1(6) . . . . ? C2 C1 C5 C4 -1.4(6) . . . . ? C6 C1 C5 C4 177.3(5) . . . . ? Ru1 C1 C5 C4 -62.0(4) . . . . ? C2 C1 C5 C10 -177.1(5) . . . . ? C6 C1 C5 C10 1.6(9) . . . . ? Ru1 C1 C5 C10 122.3(5) . . . . ? C2 C1 C5 Ru1 60.6(4) . . . . ? C6 C1 C5 Ru1 -120.7(5) . . . . ? N2 Ru1 C5 C4 -61.8(4) . . . . ? N1 Ru1 C5 C4 30.7(9) . . . . ? C3 Ru1 C5 C4 37.7(3) . . . . ? C2 Ru1 C5 C4 80.9(4) . . . . ? C1 Ru1 C5 C4 118.2(5) . . . . ? Cl1 Ru1 C5 C4 -162.1(3) . . . . ? C11 Ru1 C5 C4 -48.3(5) . . . . ? N2 Ru1 C5 C1 180.0(3) . . . . ? N1 Ru1 C5 C1 -87.5(8) . . . . ? C3 Ru1 C5 C1 -80.5(3) . . . . ? C2 Ru1 C5 C1 -37.3(3) . . . . ? C4 Ru1 C5 C1 -118.2(5) . . . . ? Cl1 Ru1 C5 C1 79.8(3) . . . . ? C11 Ru1 C5 C1 -166.5(3) . . . . ? N2 Ru1 C5 C10 60.4(6) . . . . ? N1 Ru1 C5 C10 152.9(6) . . . . ? C3 Ru1 C5 C10 159.9(6) . . . . ? C2 Ru1 C5 C10 -156.9(6) . . . . ? C1 Ru1 C5 C10 -119.6(6) . . . . ? C4 Ru1 C5 C10 122.2(7) . . . . ? Cl1 Ru1 C5 C10 -39.8(5) . . . . ? C11 Ru1 C5 C10 73.9(6) . . . . ? C12 N1 C11 N2 174.4(5) . . . . ? Ru1 N1 C11 N2 5.2(4) . . . . ? C12 N1 C11 C18 -6.5(8) . . . . ? Ru1 N1 C11 C18 -175.7(5) . . . . ? C12 N1 C11 Ru1 169.2(6) . . . . ? C15 N2 C11 N1 -169.6(5) . . . . ? Ru1 N2 C11 N1 -5.2(4) . . . . ? C15 N2 C11 C18 11.3(9) . . . . ? Ru1 N2 C11 C18 175.7(5) . . . . ? C15 N2 C11 Ru1 -164.4(6) . . . . ? N2 Ru1 C11 N1 174.0(5) . . . . ? C3 Ru1 C11 N1 78.5(4) . . . . ? C2 Ru1 C11 N1 40.4(4) . . . . ? C1 Ru1 C11 N1 23.3(11) . . . . ? C5 Ru1 C11 N1 150.9(4) . . . . ? C4 Ru1 C11 N1 119.9(3) . . . . ? Cl1 Ru1 C11 N1 -92.2(3) . . . . ? N1 Ru1 C11 N2 -174.0(5) . . . . ? C3 Ru1 C11 N2 -95.5(4) . . . . ? C2 Ru1 C11 N2 -133.6(3) . . . . ? C1 Ru1 C11 N2 -150.7(9) . . . . ? C5 Ru1 C11 N2 -23.1(5) . . . . ? C4 Ru1 C11 N2 -54.1(4) . . . . ? Cl1 Ru1 C11 N2 93.8(3) . . . . ? N2 Ru1 C11 C18 -89(8) . . . . ? N1 Ru1 C11 C18 97(8) . . . . ? C3 Ru1 C11 C18 176(8) . . . . ? C2 Ru1 C11 C18 138(8) . . . . ? C1 Ru1 C11 C18 121(7) . . . . ? C5 Ru1 C11 C18 -112(8) . . . . ? C4 Ru1 C11 C18 -143(8) . . . . ? Cl1 Ru1 C11 C18 5(8) . . . . ? C11 N1 C12 C13 104.0(6) . . . . ? Ru1 N1 C12 C13 -92.8(7) . . . . ? C11 N1 C12 C14 -129.7(6) . . . . ? Ru1 N1 C12 C14 33.5(9) . . . . ? C11 N2 C15 C17 141.1(7) . . . . ? Ru1 N2 C15 C17 -14.8(10) . . . . ? C11 N2 C15 C16 -91.4(7) . . . . ? Ru1 N2 C15 C16 112.8(6) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 0.50 _diffrn_measured_fraction_theta_full 0.000 _refine_diff_density_max 0.630 _refine_diff_density_min -0.626 _refine_diff_density_rms 0.101 #======END data_8 _database_code_CSD 194484 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H10 Cl3 N O' _chemical_formula_weight 242.52 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 9.3085(6) _cell_length_b 15.0641(10) _cell_length_c 7.4597(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1046.03(11) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 10740 _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 27.5 _exptl_crystal_description 'platelet' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.540 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.835 _exptl_absorpt_correction_type 'empirical' _exptl_absorpt_correction_T_max 0.747 _exptl_absorpt_correction_T_min 0.552 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'Imaging Plate' _diffrn_measurement_device 'Rigaku RAXIS-RAPID' _diffrn_measurement_method 'oscillation' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 2371 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0504 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.57 _diffrn_reflns_theta_max 27.47 _reflns_number_total 2371 _reflns_number_gt 1827 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction ; teXsan for Windows version 1.06 (MSC, 1997-1999) ; _computing_structure_solution ; SIR97 (Altomare, et. al. 1997) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97/2 (Sheldrick,1997)' _computing_molecular_graphics 'ORTEP III (Farrujia, 1998)' _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^)+(0.0331P)^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 SHELXL _refine_ls_extinction_coef 0.061(3) _refine_ls_extinction_expression 'Fc^*^==kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.07(8) _refine_ls_number_reflns 2371 _refine_ls_number_parameters 119 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0463 _refine_ls_R_factor_gt 0.0333 _refine_ls_wR_factor_ref 0.0741 _refine_ls_wR_factor_gt 0.0685 _refine_ls_goodness_of_fit_ref 0.966 _refine_ls_restrained_S_all 0.966 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.03446(6) 0.15867(5) 0.40372(8) 0.05551(18) Uani 1 1 d . . . Cl2 Cl 0.27543(7) 0.15393(5) 0.64941(7) 0.0618(2) Uani 1 1 d . . . Cl3 Cl 0.43227(10) 0.07644(6) 0.03446(9) 0.0758(3) Uani 1 1 d . . . O1 O 0.1721(2) 0.34575(14) 0.5841(3) 0.0659(5) Uani 1 1 d . . . N1 N 0.2323(2) 0.32933(12) 0.2873(2) 0.0448(5) Uani 1 1 d . . . C1 C 0.2689(3) 0.41933(16) 0.2278(4) 0.0608(7) Uani 1 1 d . . . H1A H 0.3277 0.4497 0.3158 0.073 Uiso 1 1 calc R . . H1B H 0.1832 0.4542 0.2049 0.073 Uiso 1 1 calc R . . C2 C 0.3530(4) 0.4020(2) 0.0540(4) 0.0772(9) Uani 1 1 d . . . H2A H 0.2916 0.4098 -0.0498 0.093 Uiso 1 1 calc R . . H2B H 0.4339 0.4424 0.0442 0.093 Uiso 1 1 calc R . . C3 C 0.4045(3) 0.30679(18) 0.0674(4) 0.0566(7) Uani 1 1 d . . . H3A H 0.4200 0.2814 -0.0505 0.068 Uiso 1 1 calc R . . H3B H 0.4929 0.3029 0.1358 0.068 Uiso 1 1 calc R . . C4 C 0.2823(2) 0.26048(14) 0.1637(3) 0.0402(5) Uani 1 1 d . . . H4 H 0.2062 0.2447 0.0788 0.048 Uiso 1 1 calc R . . C5 C 0.3154(2) 0.18195(15) 0.2879(3) 0.0393(5) Uani 1 1 d . . . H5 H 0.4139 0.1890 0.3318 0.047 Uiso 1 1 calc R . . C6 C 0.2133(3) 0.19911(16) 0.4456(3) 0.0440(5) Uani 1 1 d . . . C7 C 0.2021(2) 0.30157(17) 0.4525(3) 0.0458(6) Uani 1 1 d . . . C8 C 0.3024(3) 0.08984(17) 0.2073(4) 0.0595(7) Uani 1 1 d . . . H8A H 0.2067 0.0817 0.1585 0.071 Uiso 1 1 calc R . . H8B H 0.3176 0.0455 0.2996 0.071 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 Cl1 0.0426(3) 0.0648(4) 0.0592(3) 0.0039(3) 0.0008(3) -0.0090(3) Cl2 0.0661(4) 0.0784(5) 0.0408(3) 0.0135(3) -0.0046(3) -0.0053(4) Cl3 0.0879(6) 0.0790(5) 0.0605(4) -0.0195(4) 0.0053(4) 0.0307(5) O1 0.0650(10) 0.0728(12) 0.0600(10) -0.0228(11) 0.0155(9) 0.0057(11) N1 0.0478(10) 0.0387(11) 0.0479(9) -0.0019(8) 0.0016(8) 0.0034(10) C1 0.0708(18) 0.0435(15) 0.0681(15) 0.0007(13) -0.0097(14) 0.0041(15) C2 0.091(2) 0.0614(19) 0.0792(19) 0.0199(17) 0.013(2) -0.0109(17) C3 0.0583(14) 0.0634(17) 0.0483(13) 0.0029(13) 0.0127(12) -0.0087(14) C4 0.0409(10) 0.0433(13) 0.0363(9) -0.0013(10) -0.0015(9) 0.0013(11) C5 0.0373(10) 0.0427(13) 0.0378(9) -0.0018(9) -0.0014(8) 0.0040(10) C6 0.0425(10) 0.0511(14) 0.0384(10) 0.0041(10) 0.0007(9) -0.0022(11) C7 0.0359(10) 0.0534(15) 0.0481(11) -0.0080(11) 0.0031(10) 0.0034(11) C8 0.0711(19) 0.0464(15) 0.0610(15) -0.0066(13) 0.0064(14) 0.0081(14) _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 Cl1 C6 1.800(2) . ? Cl2 C6 1.763(2) . ? Cl3 C8 1.779(3) . ? O1 C7 1.218(3) . ? N1 C7 1.332(3) . ? N1 C4 1.464(3) . ? N1 C1 1.467(3) . ? C1 C2 1.537(4) . ? C2 C3 1.516(4) . ? C3 C4 1.515(3) . ? C4 C5 1.534(3) . ? C5 C8 1.517(3) . ? C5 C6 1.534(3) . ? C6 C7 1.548(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 C7 N1 C4 115.32(19) . . ? C7 N1 C1 128.3(2) . . ? C4 N1 C1 112.99(19) . . ? N1 C1 C2 102.5(2) . . ? C3 C2 C1 105.4(2) . . ? C4 C3 C2 103.3(2) . . ? N1 C4 C3 102.19(19) . . ? N1 C4 C5 103.29(16) . . ? C3 C4 C5 119.4(2) . . ? C8 C5 C6 114.1(2) . . ? C8 C5 C4 116.75(18) . . ? C6 C5 C4 102.08(17) . . ? C5 C6 C7 103.63(18) . . ? C5 C6 Cl2 113.16(16) . . ? C7 C6 Cl2 112.21(16) . . ? C5 C6 Cl1 112.50(15) . . ? C7 C6 Cl1 106.30(16) . . ? Cl2 C6 Cl1 108.79(12) . . ? O1 C7 N1 128.5(3) . . ? O1 C7 C6 126.0(2) . . ? N1 C7 C6 105.53(19) . . ? C5 C8 Cl3 109.70(19) . . ? 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 C7 N1 C1 C2 156.1(3) . . . . ? C4 N1 C1 C2 -1.8(3) . . . . ? N1 C1 C2 C3 -20.9(3) . . . . ? C1 C2 C3 C4 35.3(3) . . . . ? C7 N1 C4 C3 -137.5(2) . . . . ? C1 N1 C4 C3 23.4(3) . . . . ? C7 N1 C4 C5 -12.9(3) . . . . ? C1 N1 C4 C5 148.0(2) . . . . ? C2 C3 C4 N1 -35.1(3) . . . . ? C2 C3 C4 C5 -148.2(2) . . . . ? N1 C4 C5 C8 152.2(2) . . . . ? C3 C4 C5 C8 -95.3(3) . . . . ? N1 C4 C5 C6 27.1(2) . . . . ? C3 C4 C5 C6 139.5(2) . . . . ? C8 C5 C6 C7 -158.2(2) . . . . ? C4 C5 C6 C7 -31.3(2) . . . . ? C8 C5 C6 Cl2 80.0(2) . . . . ? C4 C5 C6 Cl2 -153.13(15) . . . . ? C8 C5 C6 Cl1 -43.8(2) . . . . ? C4 C5 C6 Cl1 83.06(19) . . . . ? C4 N1 C7 O1 172.4(2) . . . . ? C1 N1 C7 O1 14.9(4) . . . . ? C4 N1 C7 C6 -7.4(3) . . . . ? C1 N1 C7 C6 -164.8(2) . . . . ? C5 C6 C7 O1 -155.1(2) . . . . ? Cl2 C6 C7 O1 -32.7(3) . . . . ? Cl1 C6 C7 O1 86.2(3) . . . . ? C5 C6 C7 N1 24.7(2) . . . . ? Cl2 C6 C7 N1 147.11(17) . . . . ? Cl1 C6 C7 N1 -94.08(18) . . . . ? C6 C5 C8 Cl3 -176.95(17) . . . . ? C4 C5 C8 Cl3 64.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 0.50 _diffrn_measured_fraction_theta_full 0.000 _refine_diff_density_max 0.188 _refine_diff_density_min -0.248 _refine_diff_density_rms 0.051 #======END