#------------------------------------------------------------------------------ #$Date: 2013-12-29 13:49:26 +0200 (Sun, 29 Dec 2013) $ #$Revision: 91935 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/06/81/4068122.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_4068122 loop_ _publ_author_name 'Keske, Eric C.' 'Zenkina, Olena V.' 'Wang, Ruiyao' 'Crudden, Cathleen M.' _publ_section_title ; Synthesis and Structure of Silver and Rhodium 1,2,3-Triazol-5-ylidene Mesoionic Carbene Complexes ; _journal_issue 1 _journal_name_full Organometallics _journal_page_first 456 _journal_volume 31 _journal_year 2012 _chemical_formula_sum 'C74 H94 Ag4 Br4 Cl6 N12' _chemical_formula_weight 2115.43 _space_group_IT_number 12 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2y' _symmetry_space_group_name_H-M 'C 1 2/m 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 117.3400(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 17.0605(2) _cell_length_b 23.2997(3) _cell_length_c 11.8865(3) _cell_measurement_reflns_used 8546 _cell_measurement_temperature 180(2) _cell_measurement_theta_max 26.29 _cell_measurement_theta_min 2.49 _cell_volume 4197.15(13) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _diffrn_ambient_temperature 180(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0271 _diffrn_reflns_av_sigmaI/netI 0.0190 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 24206 _diffrn_reflns_theta_full 26.00 _diffrn_reflns_theta_max 26.00 _diffrn_reflns_theta_min 1.75 _exptl_absorpt_coefficient_mu 3.062 _exptl_absorpt_correction_T_max 0.6566 _exptl_absorpt_correction_T_min 0.5149 _exptl_absorpt_correction_type multi-scan _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.674 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 2104 _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _refine_diff_density_max 2.755 _refine_diff_density_min -2.539 _refine_diff_density_rms 0.216 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.108 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 240 _refine_ls_number_reflns 4240 _refine_ls_number_restraints 6 _refine_ls_restrained_S_all 1.109 _refine_ls_R_factor_all 0.0863 _refine_ls_R_factor_gt 0.0752 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1473P)^2^+41.4858P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2311 _refine_ls_wR_factor_ref 0.2446 _reflns_number_gt 3599 _reflns_number_total 4240 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file om201104f_si_002.cif _[local]_cod_data_source_block cc104 _[local]_cod_cif_authors_sg_H-M C2/m _cod_original_cell_volume 4197.14(13) _cod_database_code 4068122 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z' 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 Ag1 Ag 1.0000 0.65509(3) 0.5000 0.0315(3) Uani 1 2 d S Ag2 Ag 0.52839(11) 0.5000 0.64985(15) 0.0870(5) Uani 1 2 d S N1 N 0.7273(4) 0.6235(3) 0.2637(6) 0.0398(13) Uani 1 1 d . N2 N 0.7315(4) 0.6742(3) 0.2168(6) 0.0403(13) Uani 1 1 d . N3 N 0.8162(3) 0.6890(2) 0.2871(5) 0.0321(11) Uani 1 1 d . Br1 Br 0.55546(13) 0.5000 0.8771(2) 0.0863(5) Uani 1 2 d S Br2 Br 0.63524(12) 0.5000 0.5449(2) 0.0860(5) Uani 1 2 d S C1 C 0.9030(7) 0.5000 0.6218(10) 0.044(2) Uani 1 2 d S H1A H 0.9391 0.5000 0.7109 0.053 Uiso 1 2 calc SR C2 C 0.8768(5) 0.5514(3) 0.5574(7) 0.0398(15) Uani 1 1 d . H2A H 0.8951 0.5866 0.6023 0.048 Uiso 1 1 calc R C3 C 0.8239(4) 0.5518(3) 0.4266(7) 0.0355(14) Uani 1 1 d . C4 C 0.7968(6) 0.5000 0.3613(9) 0.0349(19) Uani 1 2 d S H4A H 0.7599 0.5000 0.2723 0.042 Uiso 1 2 calc SR C5 C 0.8063(4) 0.6068(3) 0.3594(6) 0.0330(13) Uani 1 1 d . C6 C 0.8662(4) 0.6503(3) 0.3756(7) 0.0339(13) Uani 1 1 d . C7 C 0.6414(5) 0.5937(4) 0.2102(10) 0.057(2) Uani 1 1 d . H7A H 0.5945 0.6214 0.1953 0.085 Uiso 1 1 calc R H7B H 0.6424 0.5643 0.2700 0.085 Uiso 1 1 calc R H7C H 0.6302 0.5754 0.1300 0.085 Uiso 1 1 calc R C8 C 0.8468(4) 0.7427(3) 0.2574(7) 0.0376(14) Uani 1 1 d . C9 C 0.8433(5) 0.7920(3) 0.3197(7) 0.0398(15) Uani 1 1 d . C10 C 0.8716(6) 0.8430(3) 0.2881(9) 0.053(2) Uani 1 1 d . H10A H 0.8697 0.8779 0.3282 0.063 Uiso 1 1 calc R C11 C 0.9024(7) 0.8429(4) 0.1987(11) 0.064(3) Uani 1 1 d . H11A H 0.9205 0.8779 0.1768 0.077 Uiso 1 1 calc R C12 C 0.9071(6) 0.7928(4) 0.1415(10) 0.062(2) Uani 1 1 d . H12A H 0.9288 0.7936 0.0809 0.074 Uiso 1 1 calc R C13 C 0.8802(5) 0.7404(4) 0.1710(8) 0.0471(17) Uani 1 1 d . C14 C 0.8108(5) 0.7920(3) 0.4206(8) 0.0459(17) Uani 1 1 d . H14A H 0.7866 0.7530 0.4218 0.055 Uiso 1 1 calc R C15 C 0.7372(7) 0.8355(5) 0.3882(11) 0.068(3) Uani 1 1 d . H15A H 0.7090 0.8293 0.4428 0.101 Uiso 1 1 calc R H15B H 0.6933 0.8309 0.2993 0.101 Uiso 1 1 calc R H15C H 0.7617 0.8744 0.4014 0.101 Uiso 1 1 calc R C16 C 0.8869(7) 0.8035(6) 0.5512(10) 0.072(3) Uani 1 1 d . H16A H 0.8654 0.8020 0.6147 0.109 Uiso 1 1 calc R H16B H 0.9116 0.8416 0.5522 0.109 Uiso 1 1 calc R H16C H 0.9328 0.7743 0.5707 0.109 Uiso 1 1 calc R C17 C 0.8915(6) 0.6843(4) 0.1150(9) 0.058(2) Uani 1 1 d . H17A H 0.8632 0.6530 0.1411 0.069 Uiso 1 1 calc R C18 C 0.8491(8) 0.6858(6) -0.0266(10) 0.084(3) Uani 1 1 d . H18A H 0.7850 0.6820 -0.0605 0.126 Uiso 1 1 calc R H18B H 0.8717 0.6541 -0.0575 0.126 Uiso 1 1 calc R H18C H 0.8627 0.7224 -0.0544 0.126 Uiso 1 1 calc R C19 C 0.9909(8) 0.6717(7) 0.1729(12) 0.099(5) Uani 1 1 d . H19A H 1.0000 0.6333 0.1473 0.149 Uiso 1 1 calc R H19B H 1.0170 0.6735 0.2655 0.149 Uiso 1 1 calc R H19C H 1.0192 0.7003 0.1430 0.149 Uiso 1 1 calc R Cl2 Cl 0.8224(9) 0.5298(7) 0.0792(11) 0.340(9) Uani 1 1 d D Cl1 Cl 0.8678(14) 0.5000 -0.0994(17) 0.340(9) Uani 1 2 d SD C21 C 0.798(2) 0.5000 -0.051(3) 0.146(17) Uani 0.60 2 d SPD C20 C 0.884(3) 0.5000 0.038(3) 0.146(17) Uani 0.40 2 d SPD 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 Ag1 0.0292(4) 0.0233(4) 0.0378(4) 0.000 0.0118(3) 0.000 Ag2 0.1098(11) 0.0577(7) 0.1014(10) 0.000 0.0554(9) 0.000 N1 0.028(3) 0.032(3) 0.049(3) 0.000(2) 0.009(2) 0.001(2) N2 0.038(3) 0.032(3) 0.044(3) 0.005(2) 0.012(3) 0.005(2) N3 0.031(3) 0.026(3) 0.038(3) 0.003(2) 0.014(2) 0.004(2) Br1 0.0956(12) 0.0659(10) 0.1089(14) 0.000 0.0569(11) 0.000 Br2 0.0743(10) 0.0755(11) 0.1166(14) 0.000 0.0511(10) 0.000 C1 0.048(6) 0.035(5) 0.038(5) 0.000 0.010(4) 0.000 C2 0.045(4) 0.030(3) 0.042(4) -0.004(3) 0.018(3) -0.002(3) C3 0.034(3) 0.023(3) 0.048(4) 0.000(3) 0.017(3) 0.002(2) C4 0.034(4) 0.027(4) 0.041(5) 0.000 0.015(4) 0.000 C5 0.031(3) 0.025(3) 0.040(3) -0.002(2) 0.014(3) -0.001(2) C6 0.036(3) 0.024(3) 0.043(3) -0.002(3) 0.019(3) 0.002(2) C7 0.032(4) 0.042(4) 0.081(6) -0.002(4) 0.013(4) -0.006(3) C8 0.033(3) 0.032(3) 0.047(4) 0.010(3) 0.018(3) 0.005(3) C9 0.036(3) 0.029(3) 0.054(4) 0.006(3) 0.020(3) 0.004(3) C10 0.052(5) 0.033(4) 0.075(6) 0.012(4) 0.032(4) 0.003(3) C11 0.060(5) 0.052(5) 0.083(6) 0.027(5) 0.035(5) 0.001(4) C12 0.059(5) 0.067(6) 0.076(6) 0.029(5) 0.045(5) 0.015(4) C13 0.045(4) 0.047(4) 0.052(4) 0.014(3) 0.024(3) 0.009(3) C14 0.050(4) 0.033(4) 0.059(4) 0.000(3) 0.027(4) 0.000(3) C15 0.068(6) 0.068(6) 0.078(6) 0.009(5) 0.044(5) 0.023(5) C16 0.066(6) 0.089(8) 0.060(6) 0.001(5) 0.027(5) 0.010(5) C17 0.058(5) 0.064(5) 0.061(5) 0.013(4) 0.036(4) 0.023(4) C18 0.081(7) 0.104(9) 0.054(6) 0.002(6) 0.021(5) 0.027(7) C19 0.071(7) 0.132(11) 0.077(7) 0.000(7) 0.018(6) 0.063(8) Cl2 0.342(12) 0.49(3) 0.276(9) -0.121(14) 0.217(9) -0.117(14) Cl1 0.342(12) 0.49(3) 0.276(9) -0.121(14) 0.217(9) -0.117(14) C21 0.12(2) 0.25(5) 0.11(2) 0.000 0.09(2) 0.000 C20 0.12(2) 0.25(5) 0.11(2) 0.000 0.09(2) 0.000 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' Br Br -0.2901 2.4595 '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' Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C6 Ag1 C6 173.9(3) . 2_756 Br1 Ag2 Br2 132.80(9) . . Br1 Ag2 Br2 121.96(8) . 5_666 Br2 Ag2 Br2 105.23(7) . 5_666 Br1 Ag2 Ag2 173.92(10) . 5_666 Br2 Ag2 Ag2 53.27(6) . 5_666 Br2 Ag2 Ag2 51.96(6) 5_666 5_666 N2 N1 C5 112.5(5) . . N2 N1 C7 118.4(6) . . C5 N1 C7 129.1(6) . . N1 N2 N3 102.7(5) . . N2 N3 C6 115.3(5) . . N2 N3 C8 118.2(5) . . C6 N3 C8 126.4(5) . . Ag2 Br2 Ag2 74.77(7) . 5_666 C2 C1 C2 120.3(9) 6_565 . C2 C1 H1A 119.8 6_565 . C2 C1 H1A 119.8 . . C1 C2 C3 120.3(7) . . C1 C2 H2A 119.9 . . C3 C2 H2A 119.9 . . C2 C3 C4 119.6(6) . . C2 C3 C5 118.7(6) . . C4 C3 C5 121.4(6) . . C3 C4 C3 119.9(9) . 6_565 C3 C4 H4A 120.0 . . C3 C4 H4A 120.0 6_565 . N1 C5 C6 106.8(6) . . N1 C5 C3 125.6(6) . . C6 C5 C3 127.5(6) . . N3 C6 C5 102.6(6) . . N3 C6 Ag1 127.9(5) . . C5 C6 Ag1 129.5(5) . . N1 C7 H7A 109.5 . . N1 C7 H7B 109.5 . . H7A C7 H7B 109.5 . . N1 C7 H7C 109.5 . . H7A C7 H7C 109.5 . . H7B C7 H7C 109.5 . . C9 C8 C13 124.2(7) . . C9 C8 N3 118.3(6) . . C13 C8 N3 117.5(6) . . C8 C9 C10 117.2(7) . . C8 C9 C14 122.6(6) . . C10 C9 C14 120.2(7) . . C11 C10 C9 120.3(8) . . C11 C10 H10A 119.8 . . C9 C10 H10A 119.8 . . C12 C11 C10 120.7(8) . . C12 C11 H11A 119.7 . . C10 C11 H11A 119.7 . . C11 C12 C13 121.1(8) . . C11 C12 H12A 119.4 . . C13 C12 H12A 119.4 . . C8 C13 C12 116.4(8) . . C8 C13 C17 122.4(7) . . C12 C13 C17 121.2(8) . . C15 C14 C16 111.1(8) . . C15 C14 C9 110.8(7) . . C16 C14 C9 110.6(7) . . C15 C14 H14A 108.1 . . C16 C14 H14A 108.1 . . C9 C14 H14A 108.1 . . C14 C15 H15A 109.5 . . C14 C15 H15B 109.5 . . H15A C15 H15B 109.5 . . C14 C15 H15C 109.5 . . H15A C15 H15C 109.5 . . H15B C15 H15C 109.5 . . C14 C16 H16A 109.5 . . C14 C16 H16B 109.5 . . H16A C16 H16B 109.5 . . C14 C16 H16C 109.5 . . H16A C16 H16C 109.5 . . H16B C16 H16C 109.5 . . C18 C17 C13 112.3(8) . . C18 C17 C19 111.9(9) . . C13 C17 C19 107.7(9) . . C18 C17 H17A 108.3 . . C13 C17 H17A 108.3 . . C19 C17 H17A 108.3 . . 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 . . Cl2 Cl2 C20 62.9(8) 6_565 . Cl2 Cl2 C21 63.7(8) 6_565 . C20 Cl2 C21 52(3) . . C20 Cl1 C21 53(3) . . C20 C21 Cl1 62.8(14) . . C20 C21 Cl2 62.3(14) . . Cl1 C21 Cl2 118(2) . . C20 C21 Cl2 62.3(14) . 6_565 Cl1 C21 Cl2 118(2) . 6_565 Cl2 C21 Cl2 52.6(15) . 6_565 C21 C20 Cl1 64.6(16) . . C21 C20 Cl2 65.5(16) . 6_565 Cl1 C20 Cl2 122(3) . 6_565 C21 C20 Cl2 65.5(16) . . Cl1 C20 Cl2 122(3) . . Cl2 C20 Cl2 54.3(16) 6_565 . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 Ag1 C6 2.075(7) . Ag1 C6 2.075(7) 2_756 Ag2 Br1 2.523(3) . Ag2 Br2 2.640(2) . Ag2 Br2 2.686(3) 5_666 Ag2 Ag2 3.234(3) 5_666 N1 N2 1.321(9) . N1 C5 1.362(9) . N1 C7 1.477(9) . N2 N3 1.340(8) . N3 C6 1.350(8) . N3 C8 1.459(8) . Br2 Ag2 2.686(3) 5_666 C1 C2 1.381(9) 6_565 C1 C2 1.381(9) . C1 H1A 0.9500 . C2 C3 1.393(10) . C2 H2A 0.9500 . C3 C4 1.395(8) . C3 C5 1.466(9) . C4 C3 1.395(8) 6_565 C4 H4A 0.9500 . C5 C6 1.389(9) . C7 H7A 0.9800 . C7 H7B 0.9800 . C7 H7C 0.9800 . C8 C9 1.383(10) . C8 C13 1.386(11) . C9 C10 1.398(10) . C9 C14 1.535(11) . C10 C11 1.385(14) . C10 H10A 0.9500 . C11 C12 1.372(15) . C11 H11A 0.9500 . C12 C13 1.404(12) . C12 H12A 0.9500 . C13 C17 1.519(12) . C14 C15 1.520(12) . C14 C16 1.522(13) . C14 H14A 1.0000 . C15 H15A 0.9800 . C15 H15B 0.9800 . C15 H15C 0.9800 . C16 H16A 0.9800 . C16 H16B 0.9800 . C16 H16C 0.9800 . C17 C18 1.496(13) . C17 C19 1.537(14) . C17 H17A 1.0000 . C18 H18A 0.9800 . C18 H18B 0.9800 . C18 H18C 0.9800 . C19 H19A 0.9800 . C19 H19B 0.9800 . C19 H19C 0.9800 . Cl2 Cl2 1.39(3) 6_565 Cl2 C20 1.52(2) . Cl2 C21 1.56(2) . Cl1 C20 1.52(2) . Cl1 C21 1.54(2) . C21 C20 1.36(8) . C21 Cl2 1.56(2) 6_565 C20 Cl2 1.52(2) 6_565 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_4 C5 N1 N2 N3 -0.3(8) . . C7 N1 N2 N3 178.6(7) . . N1 N2 N3 C6 0.4(8) . . N1 N2 N3 C8 177.1(6) . . Br1 Ag2 Br2 Ag2 180.0 . 5_666 Br2 Ag2 Br2 Ag2 0.0 5_666 5_666 C2 C1 C2 C3 0.0(16) 6_565 . C1 C2 C3 C4 0.5(12) . . C1 C2 C3 C5 -172.7(8) . . C2 C3 C4 C3 -1.0(14) . 6_565 C5 C3 C4 C3 172.0(5) . 6_565 N2 N1 C5 C6 0.1(8) . . C7 N1 C5 C6 -178.7(8) . . N2 N1 C5 C3 -177.2(6) . . C7 N1 C5 C3 4.0(12) . . C2 C3 C5 N1 -139.3(7) . . C4 C3 C5 N1 47.6(11) . . C2 C3 C5 C6 44.0(10) . . C4 C3 C5 C6 -129.1(8) . . N2 N3 C6 C5 -0.4(8) . . C8 N3 C6 C5 -176.7(6) . . N2 N3 C6 Ag1 178.1(5) . . C8 N3 C6 Ag1 1.8(10) . . N1 C5 C6 N3 0.2(7) . . C3 C5 C6 N3 177.4(6) . . N1 C5 C6 Ag1 -178.3(5) . . C3 C5 C6 Ag1 -1.1(11) . . C6 Ag1 C6 N3 -152.7(6) 2_756 . C6 Ag1 C6 C5 25.4(6) 2_756 . N2 N3 C8 C9 91.9(8) . . C6 N3 C8 C9 -91.9(8) . . N2 N3 C8 C13 -90.2(8) . . C6 N3 C8 C13 86.0(9) . . C13 C8 C9 C10 3.2(11) . . N3 C8 C9 C10 -179.0(6) . . C13 C8 C9 C14 -176.2(7) . . N3 C8 C9 C14 1.5(10) . . C8 C9 C10 C11 -0.6(12) . . C14 C9 C10 C11 178.8(8) . . C9 C10 C11 C12 -1.1(15) . . C10 C11 C12 C13 0.5(15) . . C9 C8 C13 C12 -3.8(11) . . N3 C8 C13 C12 178.4(7) . . C9 C8 C13 C17 173.5(7) . . N3 C8 C13 C17 -4.3(11) . . C11 C12 C13 C8 1.8(13) . . C11 C12 C13 C17 -175.5(9) . . C8 C9 C14 C15 -125.8(8) . . C10 C9 C14 C15 54.7(10) . . C8 C9 C14 C16 110.6(9) . . C10 C9 C14 C16 -68.9(10) . . C8 C13 C17 C18 127.7(9) . . C12 C13 C17 C18 -55.1(12) . . C8 C13 C17 C19 -108.7(10) . . C12 C13 C17 C19 68.5(11) . . C20 Cl1 C21 Cl2 30.1(13) . . C20 Cl1 C21 Cl2 -30.1(13) . 6_565 Cl2 Cl2 C21 C20 -74.9(8) 6_565 . Cl2 Cl2 C21 Cl1 -105.2(17) 6_565 . C20 Cl2 C21 Cl1 -30.3(13) . . C20 Cl2 C21 Cl2 74.9(8) . 6_565 Cl2 C21 C20 Cl1 -149.9(8) . . Cl2 C21 C20 Cl1 149.9(8) 6_565 . Cl1 C21 C20 Cl2 -149.9(8) . 6_565 Cl2 C21 C20 Cl2 60.1(15) . 6_565 Cl1 C21 C20 Cl2 149.9(8) . . Cl2 C21 C20 Cl2 -60.1(15) 6_565 . C21 Cl1 C20 Cl2 32.6(17) . 6_565 C21 Cl1 C20 Cl2 -32.6(17) . . Cl2 Cl2 C20 C21 76.5(9) 6_565 . Cl2 Cl2 C20 Cl1 109(2) 6_565 . C21 Cl2 C20 Cl1 32.3(17) . . C21 Cl2 C20 Cl2 -76.5(9) . 6_565 _journal_paper_doi 10.1021/om201104f