# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2002 data_st1112 _database_code_CSD 187538 #=============================================================================== _audit_creation_date 28-03-02 _journal_coden_Cambridge 182 loop_ _publ_author_name 'Hosseini, M.' 'Jouaiti, Abdelaziz' 'Kyritsakas, N.' _publ_contact_author_name 'Prof M Hosseini' _publ_contact_author_address ; Laboratoire de Chimie de Coordination Organique Universite Louis Pasteur 4 rue Blaise Pascal 67000 Strasbourg FRANCE ; _publ_contact_author_email 'HOSSEINI@CHIMIE.U-STRASBG.FR' _publ_requested_journal 'Chemical Communications' _publ_section_title ; Chirality and acentric packing of 1-D coordination networks ; _publ_section_references ; Burla, M.C., Camalli, M., Cascarano, G.,Giacovazzo, C., Polidori, G., Spagna, R. &Viterbo, D. (1989). SIR. J. Appl. Cryst. 22, 389-393. OpenMoleN, Interactive Intelligent Structure solution (1997) Nonius B.V., Delft, The Netherlands. KappaCCD Operation Manual (1997), Nonius B.V., Delft, The Nederlands. Otwinowski, Z. & Minor, W. (1997), Methods in Enzymology, 276, 307-326. Walker, N. & Stuart, D. (1983). Acta Cryst., A39, 158-166. ; #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C25 H29 Cl11 Co N4 O2' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C25 H29 Cl11 Co N4 O2' _chemical_formula_weight 866.45 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C ? 0.002 0.002 International_Tables_Vol_IV_Table_2.3.1 H ? 0.000 0.000 International_Tables_Vol_IV_Table_2.3.1 Cl ? 0.132 0.159 International_Tables_Vol_IV_Table_2.3.1 Co ? 0.299 0.973 International_Tables_Vol_IV_Table_2.3.1 N ? 0.004 0.003 International_Tables_Vol_IV_Table_2.3.1 O ? 0.008 0.006 International_Tables_Vol_IV_Table_2.3.1 #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2 1' _symmetry_space_group_name_Hall ' C 2y' loop_ _symmetry_equiv_pos_as_xyz 'x,y,z' -x,+y,-z 1/2+x,1/2+y,+z 1/2-x,1/2+y,-z _cell_length_a 26.1974(8) _cell_length_b 11.2679(4) _cell_length_c 16.6366(5) _cell_angle_alpha 90 _cell_angle_beta 125.960(5) _cell_angle_gamma 90 _cell_volume 3975.1(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173 _cell_measurement_reflns_used 10938 _cell_measurement_theta_min 1.4 _cell_measurement_theta_max 30.0 _cell_special_details ; Cell parameters refined using Scalepack part of DENZO Z. Otwinowski, W. Minor, 1997 ; _exptl_crystal_description prism _exptl_crystal_colour 'brown' _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.45 _exptl_crystal_density_method 'none' _exptl_crystal_F_000 1748 _exptl_absorpt_coefficient_mu 1.199 _exptl_absorpt_correction_type refdelf_(Walker_&_Stuart,_1983) _exptl_absorpt_correction_T_min 0.795 _exptl_absorpt_correction_T_max 0.869 #=============================================================================== # 7. EXPERIMENTAL DATA _diffrn_special_details ; ? ; _diffrn_ambient_temperature 173 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type Mo-K\a _diffrn_source xray_tube _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method '\p scans' _diffrn_measurement_details ; 10938 reflections were collected using program Collect ("Collect" Data collection software, Nonius B.V., 1998) The conditions were as follow : crystal to detector distance = 36. mm. Scan angle = 1.8 deg 1 scans of 80 sec per frame. Data collection was divided into 2 set(s) with the following starting angles and number of frames : Set 1 Theta = 8.80 Omega = 0.00 Kappa = 0.00 90 frames Set 2 Theta = -7.20 Kappa = -154.90 Phi = 0.00 19 frames Friedel pairs were averaged. Internal R = 0.05 ; _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 10938 _diffrn_reflns_av_R_equivalents 0.050 _diffrn_reflns_av_sigmaI/netI 0.333 _diffrn_reflns_limit_h_min -36 _diffrn_reflns_limit_h_max 36 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.5 _diffrn_reflns_theta_max 29.97 _reflns_number_total 6009 _reflns_number_gt 3591 _reflns_threshold_expression >3.0\s(I) _computing_structure_solution Direct_methods_(SIR,_Burla_et_al.,_1989) _computing_structure_refinement LSFM_OpenMoleN_(_1997) _computing_molecular_graphics ? _computing_publication_material CIFGEN_IN_OpenMoleN_(_1997) #=============================================================================== # 8. REFINEMENT DATA _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme sigma _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_expression ? _refine_ls_extinction_coef ? _refine_ls_abs_structure_Flack 0.04(2) _refine_ls_number_reflns 3591 _refine_ls_number_parameters 428 _refine_ls_number_restraints 41 _refine_ls_number_constraints 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_R_factor_all 0.135 _refine_ls_R_factor_gt 0.078 _refine_ls_wR_factor_all 0.218 _refine_ls_wR_factor_ref 0.114 _refine_ls_goodness_of_fit_all 2.771 _refine_ls_goodness_of_fit_ref 1.358 _refine_ls_shift/su_max 0.000 _refine_ls_shift/esd_mean 0.010 _refine_diff_density_max 0.673 _refine_diff_density_min -0.142 #=============================================================================== # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom _atom_site_type_symbol CO1 0.5000 0.7756 0.5000 0.0201(7) 0.500 Uani ? ? Co CL1 0.5993(1) 0.7780(3) 0.6661(2) 0.030(1) 1.000 Uani ? ? Cl N1 0.4449(5) 0.828(1) 0.5585(7) 0.026(4) 1.000 Uani ? ? N C1 0.4394(5) 0.939(1) 0.5594(7) 0.025(4) 1.000 Uani ? ? C O1 0.4035(4) 0.9853(9) 0.5854(6) 0.037(4) 1.000 Uani ? ? O C2 0.3765(6) 0.884(1) 0.6006(9) 0.042(5) 1.000 Uani ? ? C C3 0.4045(5) 0.776(1) 0.5840(7) 0.028(4) 1.000 Uani ? ? C C4 0.4409(6) 0.692(1) 0.6731(8) 0.034(5) 1.000 Uani ? ? C C5 0.3962(7) 0.635(2) 0.695(1) 0.062(7) 1.000 Uani ? ? C C6 0.4975(7) 0.756(2) 0.7652(9) 0.048(7) 1.000 Uani ? ? C C7 0.4701(5) 1.023(1) 0.5310(8) 0.030(5) 1.000 Uani ? ? C C8 0.4687(5) 1.144(1) 0.5317(8) 0.029(5) 1.000 Uani ? ? C C9 0.5000 1.207(2) 0.5000 0.026(7) 0.500 Uani ? ? C N2 0.5000 0.961(1) 0.5000 0.020(5) 0.500 Uani ? ? N N3 0.5000 1.586(1) 0.5000 0.021(5) 0.500 Uani ? ? N C10 0.4479(5) 1.526(1) 0.4704(8) 0.026(5) 1.000 Uani ? ? C C11 0.4463(6) 1.404(1) 0.4701(9) 0.033(5) 1.000 Uani ? ? C C12 0.5000 1.339(2) 0.5000 0.023(6) 0.500 Uani ? ? C CO2 0.5000 1.0533(2) 1.0000 0.0229(8) 0.500 Uani ? ? Co CL2 0.4301(1) 1.0462(4) 0.8219(2) 0.034(1) 1.000 Uani ? ? Cl N4 0.5834(4) 1.1076(9) 1.0012(7) 0.026(4) 1.000 Uani ? ? N C13 0.5890(5) 1.219(1) 1.0014(8) 0.027(5) 1.000 Uani ? ? C O2 0.6371(3) 1.2665(8) 1.0057(6) 0.031(3) 1.000 Uani ? ? O C14 0.6759(5) 1.167(1) 1.015(1) 0.036(5) 1.000 Uani ? ? C C15 0.6381(5) 1.055(1) 1.0053(8) 0.031(5) 1.000 Uani ? ? C C16 0.6158(6) 0.980(1) 0.9142(8) 0.032(5) 1.000 Uani ? ? C C17 0.6695(6) 0.919(2) 0.925(1) 0.046(6) 1.000 Uani ? ? C C18 0.5739(6) 1.049(2) 0.8136(9) 0.049(6) 1.000 Uani ? ? C C19 0.5439(5) 1.299(1) 1.0000(8) 0.024(5) 1.000 Uani ? ? C C20 0.5459(5) 1.425(1) 0.9995(8) 0.024(4) 1.000 Uani ? ? C C21 0.5000 1.487(2) 1.0000 0.025(6) 0.500 Uani ? ? C N5 0.5000 1.241(1) 1.0000 0.026(5) 0.500 Uani ? ? N N6 0.5000 1.865(1) 1.0000 0.027(6) 0.500 Uani ? ? N C22 0.4461(5) 1.805(1) 0.9496(8) 0.031(5) 1.000 Uani ? ? C C23 0.4434(5) 1.681(1) 0.9478(9) 0.028(5) 1.000 Uani ? ? C C24 0.5000 1.619(1) 1.0000 0.017(6) 0.500 Uani ? ? C C25 0.624(1) 0.525(2) 0.812(1) 0.025(9) 0.500 Uani ? ? C CL3 0.5552(3) 0.4401(8) 0.7701(5) 0.037(3) 0.500 Uani ? ? Cl CL4 0.6782(3) 0.4394(9) 0.8117(5) 0.056(3) 0.500 Uani ? ? Cl CL5 0.6565(3) 0.5796(6) 0.9317(4) 0.028(2) 0.500 Uani ? ? Cl C26 0.2722(8) 1.037(2) 0.681(1) 0.08(1) 1.000 Uani ? ? C CL6 0.2624(3) 0.8947(6) 0.7023(5) 0.097(3) 1.000 Uani ? ? Cl CL7 0.2522(3) 1.0657(9) 0.5622(4) 0.121(4) 1.000 Uani ? ? Cl CL8 0.2239(2) 1.1374(6) 0.6959(4) 0.077(3) 1.000 Uani ? ? Cl C27 0.380(1) 1.285(4) 0.657(2) 0.06(1) 0.500 Uani ? ? C CL9 0.3366(5) 1.299(1) 0.5427(7) 0.101(6) 0.500 Uani ? ? Cl CL10 0.4544(4) 1.309(1) 0.7216(7) 0.104(6) 0.500 Uani ? ? Cl CL11 0.3479(4) 1.3349(9) 0.7229(6) 0.083(4) 0.500 Uani ? ? Cl C28 0.2072(9) 1.520(2) 0.727(1) 0.07(1) 1.000 Uani ? ? C CL12 0.2735(2) 1.4471(6) 0.8286(3) 0.066(2) 1.000 Uani ? ? Cl CL13 0.1886(3) 1.6458(7) 0.7602(5) 0.157(4) 1.000 Uani ? ? Cl CL14 0.2171(3) 1.5498(9) 0.6352(4) 0.102(4) 1.000 Uani ? ? Cl H1 0.3319 0.8845 0.5542 0.0502 1.000 Uiso calc C2 H H2 0.3876 0.8840 0.6662 0.0502 1.000 Uiso calc C2 H H3 0.3723 0.7256 0.5335 0.0373 1.000 Uiso calc C3 H H4 0.4579 0.6294 0.6573 0.0458 1.000 Uiso calc C4 H H5 0.4197 0.5834 0.7503 0.0765 1.000 Uiso calc C5 H H6 0.3774 0.6957 0.7089 0.0765 1.000 Uiso calc C5 H H7 0.3643 0.5912 0.6384 0.0765 1.000 Uiso calc C5 H H8 0.5193 0.7023 0.8194 0.0641 1.000 Uiso calc C6 H H9 0.5253 0.7843 0.7504 0.0641 1.000 Uiso calc C6 H H10 0.4825 0.8212 0.7823 0.0641 1.000 Uiso calc C6 H H11 0.4470 1.1847 0.5532 0.0387 1.000 Uiso calc C8 H H12 0.4106 1.5681 0.4487 0.0356 1.000 Uiso calc C10 H H13 0.4085 1.3638 0.4494 0.0457 1.000 Uiso calc C11 H H14 0.7158 1.1681 1.0783 0.0488 1.000 Uiso calc C14 H H15 0.6819 1.1687 0.9643 0.0488 1.000 Uiso calc C14 H H16 0.6632 1.0014 1.0585 0.0416 1.000 Uiso calc C15 H H17 0.5888 0.9207 0.9111 0.0470 1.000 Uiso calc C16 H H18 0.6546 0.8725 0.8676 0.0606 1.000 Uiso calc C17 H H19 0.6986 0.9766 0.9324 0.0606 1.000 Uiso calc C17 H H20 0.6900 0.8693 0.9819 0.0606 1.000 Uiso calc C17 H H21 0.5616 0.9972 0.7600 0.0656 1.000 Uiso calc C18 H H22 0.5374 1.0787 0.8062 0.0656 1.000 Uiso calc C18 H H23 0.5973 1.1135 0.8136 0.0656 1.000 Uiso calc C18 H H24 0.5774 1.4653 0.9988 0.0322 1.000 Uiso calc C20 H H25 0.4077 1.8486 0.9130 0.0404 1.000 Uiso calc C22 H H26 0.4041 1.6406 0.9122 0.0406 1.000 Uiso calc C23 H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 _atom_site_aniso_type_symbol CO1 0.0376(8) 0.0078(8) 0.0279(7) 0.0000 0.0199(5) 0.0000 Co CL1 0.039(1) 0.024(1) 0.0295(9) -0.002(1) 0.0180(7) -0.003(1) Cl N1 0.041(4) 0.016(5) 0.027(3) 0.003(4) 0.018(3) 0.001(4) N C1 0.037(4) 0.014(5) 0.031(4) -0.003(4) 0.023(3) -0.002(4) C O1 0.041(3) 0.023(4) 0.054(3) 0.002(3) 0.034(2) 0.001(4) O C2 0.052(5) 0.028(7) 0.048(5) -0.008(5) 0.037(3) -0.005(5) C C3 0.035(4) 0.021(5) 0.029(4) -0.011(5) 0.018(3) -0.003(5) C C4 0.060(5) 0.021(6) 0.031(4) -0.006(5) 0.031(3) -0.003(4) C C5 0.081(7) 0.051(9) 0.056(6) -0.028(7) 0.047(4) -0.008(7) C C6 0.074(7) 0.042(9) 0.035(5) -0.010(7) 0.034(4) -0.005(6) C C7 0.032(4) 0.022(6) 0.039(4) 0.000(4) 0.024(3) 0.001(4) C C8 0.037(4) 0.016(5) 0.040(4) 0.005(4) 0.025(3) -0.005(4) C C9 0.045(7) 0.011(7) 0.036(6) 0.0000 0.025(4) 0.0000 C N2 0.047(6) 0.005(6) 0.033(5) 0.0000 0.023(4) 0.0000 N N3 0.034(5) 0.011(6) 0.026(4) 0.0000 0.019(3) 0.0000 N C10 0.033(4) 0.017(6) 0.031(4) 0.002(4) 0.018(3) -0.003(4) C C11 0.029(5) 0.026(6) 0.044(5) -0.002(5) 0.019(3) 0.005(5) C C12 0.029(6) 0.016(7) 0.024(6) 0.0000 0.012(4) 0.0000 C CO2 0.0345(8) 0.0118(9) 0.0296(7) 0.0000 0.0177(5) 0.0000 Co CL2 0.042(1) 0.030(1) 0.030(1) 0.002(1) 0.0177(7) 0.000(1) Cl N4 0.032(4) 0.016(4) 0.035(4) 0.001(4) 0.021(2) -0.006(4) N C13 0.035(4) 0.018(6) 0.032(4) 0.001(4) 0.022(3) -0.000(4) C O2 0.041(3) 0.014(4) 0.052(3) 0.003(3) 0.032(2) -0.001(4) O C14 0.034(5) 0.025(6) 0.056(5) -0.005(5) 0.028(3) -0.011(5) C C15 0.045(5) 0.019(5) 0.035(4) 0.005(5) 0.025(3) -0.001(5) C C16 0.059(6) 0.020(6) 0.027(4) -0.006(5) 0.024(3) -0.009(4) C C17 0.048(6) 0.043(8) 0.046(5) 0.006(6) 0.026(4) -0.010(6) C C18 0.041(5) 0.07(1) 0.039(5) 0.004(8) 0.024(3) 0.003(8) C C19 0.038(5) 0.014(6) 0.026(4) 0.002(4) 0.017(3) 0.000(4) C C20 0.029(4) 0.017(5) 0.029(4) -0.001(4) 0.017(3) -0.004(4) C C21 0.035(6) 0.011(7) 0.040(6) 0.0000 0.025(4) 0.0000 C N5 0.042(5) 0.010(6) 0.041(5) 0.0000 0.029(3) 0.0000 N N6 0.039(6) 0.023(7) 0.022(5) 0.0000 0.015(4) 0.0000 N C22 0.038(5) 0.026(7) 0.030(4) 0.004(5) 0.020(3) 0.003(4) C C23 0.037(5) 0.016(5) 0.038(5) -0.005(5) 0.020(3) -0.004(5) C C24 0.039(7) 0.009(6) 0.014(5) 0.0000 0.013(4) 0.0000 C C25 0.025(8) 0.02(1) 0.025(7) 0.000(8) 0.015(5) 0.000(8) C CL3 0.037(3) 0.045(4) 0.030(3) 0.017(3) 0.000(2) -0.006(3) Cl CL4 0.054(3) 0.069(5) 0.045(2) 0.021(3) 0.035(2) -0.001(3) Cl CL5 0.039(2) 0.026(3) 0.021(2) 0.001(2) 0.016(1) 0.003(2) Cl C26 0.057(7) 0.09(2) 0.081(9) 0.02(1) 0.035(6) -0.01(1) C CL6 0.095(3) 0.065(4) 0.148(4) -0.002(3) 0.074(2) -0.013(3) Cl CL7 0.125(3) 0.138(5) 0.102(3) 0.062(3) 0.068(2) 0.014(4) Cl CL8 0.075(2) 0.078(3) 0.079(2) 0.003(3) 0.040(2) -0.016(3) Cl C27 0.08(1) 0.09(2) 0.03(1) 0.06(1) 0.013(9) -0.01(1) C CL9 0.131(6) 0.101(9) 0.077(4) 0.041(6) 0.071(3) 0.041(5) Cl CL10 0.090(4) 0.11(1) 0.110(4) 0.015(5) 0.078(2) 0.020(6) Cl CL11 0.134(4) 0.038(5) 0.110(4) -0.000(4) 0.098(2) -0.004(4) Cl C28 0.084(9) 0.05(1) 0.10(1) -0.007(9) 0.055(7) 0.009(9) C CL12 0.064(2) 0.082(4) 0.055(2) 0.008(3) 0.025(1) 0.008(2) Cl CL13 0.205(3) 0.071(4) 0.266(4) 0.047(3) 0.198(2) 0.048(4) Cl CL14 0.158(4) 0.111(5) 0.060(2) 0.013(5) 0.052(2) 0.009(4) Cl # 10. MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag CO1 CL1 2.442(3) . . ? CO1 CL1 2.442(3) . 2_656 ? CO1 N1 2.24(1) . . ? CO1 N1 2.24(1) . 2_656 ? CO1 N2 2.08(2) . . ? CO1 N2 2.08(2) . 2_656 ? CO1 N3 2.13(2) . ._545 ? CO1 N3 2.13(2) . 2_646 ? CO2 CL2 2.401(3) . . ? CO2 CL2 2.401(3) . 2_657 ? CO2 N4 2.26(1) . . ? CO2 N4 2.26(1) . 2_657 ? CO2 N5 2.11(2) . . ? CO2 N5 2.11(2) . 2_657 ? CO2 N6 2.12(2) . ._545 ? CO2 N6 2.12(2) . 2_647 ? N1 C1 1.26(2) . . ? N1 C3 1.47(2) . . ? C1 O1 1.35(2) . . ? C1 C7 1.48(2) . . ? O1 C2 1.44(2) . . ? C2 C3 1.53(2) . . ? C3 C4 1.53(2) . . ? C4 C5 1.55(2) . . ? C4 C6 1.55(2) . . ? C7 C8 1.37(2) . . ? C7 N2 1.36(2) . . ? C7 N2 1.36(2) . 2_656 ? C8 C9 1.40(2) . . ? C8 C9 1.40(2) . 2_656 ? C9 C12 1.48(3) . . ? C9 C12 1.48(3) . 2_656 ? N3 C10 1.34(2) . . ? N3 C10 1.34(2) . 2_656 ? C10 C11 1.37(2) . . ? C11 C12 1.39(2) . . ? C11 C12 1.39(2) . 2_656 ? N4 C13 1.26(2) . . ? N4 C15 1.51(2) . . ? C13 O2 1.33(2) . . ? C13 C19 1.48(2) . . ? O2 C14 1.46(2) . . ? C14 C15 1.54(2) . . ? C15 C16 1.53(2) . . ? C16 C17 1.48(2) . . ? C16 C18 1.57(2) . . ? C19 C20 1.42(2) . . ? C19 N5 1.32(2) . . ? C19 N5 1.32(2) . 2_657 ? C20 C21 1.40(2) . . ? C20 C21 1.40(2) . 2_657 ? C21 C24 1.49(2) . . ? C21 C24 1.49(2) . 2_657 ? N6 C22 1.33(2) . . ? N6 C22 1.33(2) . 2_657 ? C22 C23 1.40(2) . . ? C23 C24 1.39(2) . . ? C23 C24 1.39(2) . 2_657 ? C25 CL3 1.78(3) . . ? C25 CL4 1.73(3) . . ? C25 CL5 1.76(3) . . ? C26 CL6 1.70(3) . . ? C26 CL7 1.76(3) . . ? C26 CL8 1.81(2) . . ? C27 CL9 1.54(4) . . ? C27 CL10 1.59(5) . . ? C27 CL11 1.83(4) . . ? C28 CL12 1.76(2) . . ? C28 CL13 1.70(3) . . ? C28 CL14 1.73(3) . . ? loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag ? ? ? ? ? ? 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag CL1 CO1 CL1 178.7(2) . . 2_656 ? CL1 CO1 N1 92.0(3) . . . ? CL1 CO1 N1 87.6(3) . . 2_656 ? CL1 CO1 N2 89.4(1) . . . ? CL1 CO1 N3 90.6(1) . . ._545 ? CL1 CO1 N1 87.6(3) 2_656 . . ? CL1 CO1 N1 92.0(3) 2_656 . 2_656 ? CL1 CO1 N2 89.4(1) 2_656 . . ? CL1 CO1 N3 90.6(1) 2_656 . ._545 ? N1 CO1 N1 149.5(6) . . 2_656 ? N1 CO1 N2 74.8(3) . . . ? N1 CO1 N3 105.2(3) . . ._545 ? N1 CO1 N2 74.8(3) 2_656 . . ? N1 CO1 N3 105.2(3) 2_656 . ._545 ? N2 CO1 N3 180.00 . . ._545 ? CL2 CO2 CL2 176.2(2) . . 2_657 ? CL2 CO2 N4 93.0(3) . . . ? CL2 CO2 N4 88.0(3) . . 2_657 ? CL2 CO2 N5 91.9(1) . . . ? CL2 CO2 N6 88.1(1) . . ._545 ? CL2 CO2 N4 88.0(3) 2_657 . . ? CL2 CO2 N4 93.0(3) 2_657 . 2_657 ? CL2 CO2 N5 91.9(1) 2_657 . . ? CL2 CO2 N6 88.1(1) 2_657 . ._545 ? N4 CO2 N4 148.5(6) . . 2_657 ? N4 CO2 N5 74.3(3) . . . ? N4 CO2 N6 105.7(3) . . ._545 ? N4 CO2 N5 74.3(3) 2_657 . . ? N4 CO2 N6 105.7(3) 2_657 . ._545 ? N5 CO2 N6 180.00 . . ._545 ? C1 N1 C3 106(1) . . . ? N1 C1 O1 119(1) . . . ? N1 C1 C7 122(1) . . . ? O1 C1 C7 118(1) . . . ? C1 O1 C2 104(1) . . . ? O1 C2 C3 105(1) . . . ? N1 C3 C2 103(1) . . . ? N1 C3 C4 112(1) . . . ? C2 C3 C4 114(1) . . . ? C3 C4 C5 110(1) . . . ? C3 C4 C6 111(1) . . . ? C5 C4 C6 112(1) . . . ? C1 C7 C8 127(1) . . . ? C1 C7 N2 109(1) . . . ? C8 C7 N2 122(1) . . . ? C7 C8 C9 118(1) . . . ? C8 C9 C8 118(1) . . 2_656 ? C8 C9 C12 120.5(9) . . . ? C8 C9 C12 120.5(9) 2_656 . . ? C7 N2 C7 118(1) . . 2_656 ? C10 N3 C10 118(1) . . 2_656 ? N3 C10 C11 122(1) . . . ? C10 C11 C12 120(1) . . . ? C9 C12 C11 121(1) . . . ? C9 C12 C11 121(1) . . 2_656 ? C11 C12 C11 116(1) . . 2_656 ? C13 N4 C15 106(1) . . . ? N4 C13 O2 120(1) . . . ? N4 C13 C19 121(1) . . . ? O2 C13 C19 118(1) . . . ? C13 O2 C14 105(1) . . . ? O2 C14 C15 104(1) . . . ? N4 C15 C14 102(1) . . . ? N4 C15 C16 111(1) . . . ? C14 C15 C16 114(1) . . . ? C15 C16 C17 110(1) . . . ? C15 C16 C18 113(1) . . . ? C17 C16 C18 112(1) . . . ? C13 C19 C20 125(1) . . . ? C13 C19 N5 112(1) . . . ? C20 C19 N5 122(1) . . . ? C19 C20 C21 117(1) . . . ? C20 C21 C20 119(1) . . 2_657 ? C20 C21 C24 120.2(9) . . . ? C20 C21 C24 120.2(9) 2_657 . . ? C19 N5 C19 120(1) . . 2_657 ? C22 N6 C22 118(1) . . 2_657 ? N6 C22 C23 123(1) . . . ? C22 C23 C24 117(1) . . . ? C21 C24 C23 120.2(9) . . . ? C21 C24 C23 120.2(9) . . 2_657 ? C23 C24 C23 119(1) . . 2_657 ? CL3 C25 CL4 110(1) . . . ? CL3 C25 CL5 109(1) . . . ? CL4 C25 CL5 110(1) . . . ? CL6 C26 CL7 114(1) . . . ? CL6 C26 CL8 111(1) . . . ? CL7 C26 CL8 105(1) . . . ? CL9 C27 CL10 123(3) . . . ? CL9 C27 CL11 115(2) . . . ? CL10 C27 CL11 110(2) . . . ? CL12 C28 CL13 112(1) . . . ? CL12 C28 CL14 111(1) . . . ? CL13 C28 CL14 110(1) . . . ?