#------------------------------------------------------------------------------ #$Date: 2015-01-07 18:25:02 +0200 (Wed, 07 Jan 2015) $ #$Revision: 129439 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/30/83/4308356.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_4308356 loop_ _publ_author_name 'Xiangting Zhou' 'Anthony I. Day' 'Alison J. Edwards' 'Anthony C. Willis' 'W. Gregory Jackson' _publ_contact_author_address ; Research School of Chemistry, Australian National University, Canberra, A. C. T. 0200, Australia ; _publ_contact_author_email ' willis@rsc.anu.edu.au ' _publ_contact_author_fax ' 61 2 6125 0750 ' _publ_contact_author_name ' Anthony C. Willis ' _publ_contact_author_phone ' 61 2 6125 4109 ' _publ_section_title ; Facile C-H Bond Activation: Synthesis of the N4C Donor Set Pentadentate Ligand 1,4-Bis(2-pyridylmethyl)-1,4-diazacyclononane (dmpdacn) and a Structural Study of Its Alkyl-Cobalt(III) Complex [Co(dmpdacn-C)(OH2)](ClO4)2.H2O and Its Hydroxylated Derivative [Co(dmpdacnOH-O)Cl](ClO4)2.C3H6O ; _journal_name_full 'Inorganic Chemistry' _journal_page_first 452 _journal_page_last 460 _journal_volume 44 _journal_year 2005 _chemical_compound_source ; ? ; _chemical_formula_moiety ' C19 H27 Co N4 O 2+, 2(Cl O4 -), H2 O' _chemical_formula_sum 'C19 H29 Cl2 Co N4 O10' _chemical_formula_weight 603.30 _chemical_melting_point ? _chemical_name_systematic ; ? ; _space_group_IT_number 9 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'C -2yc' _symmetry_space_group_name_H-M 'C 1 c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _audit_creation_date 03-30-10 _audit_creation_method CRYSTALS_ver_12-03-99 _audit_update_record ; Report for wgj2 C19 H29 Cl2 Co N4 O10 W. Greg Jackson and Xiangting Zhou, ADFA 2000-05-01 acw finishes refinement and compiles cif 2000-05-02 passes checkcif with minor alerts 2003-10-29 re-refined in CRYSTALS, relabelled, cif for publication ; _cell_angle_alpha 90 _cell_angle_beta 108.4631(13) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.1169(2) _cell_length_b 25.5635(6) _cell_length_c 11.4461(2) _cell_measurement_reflns_used 18207 _cell_measurement_temperature 295 _cell_measurement_theta_max 27 _cell_measurement_theta_min 3 _cell_volume 2530.32(9) _computing_cell_refinement ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _computing_data_collection ; COLLECT (Nonius BV, 1997) ; _computing_data_reduction ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _computing_molecular_graphics ; ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997) ; _computing_publication_material ; CRYSTALS (Watkin et al 2001) ; _computing_structure_refinement ; CRYSTALS (Watkin et al 2001) ; _computing_structure_solution ; SIR92 (Altomare et al, 1994) ; _diffrn_ambient_temperature 295 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type ; Enraf Nonius Kappa CCD ; _diffrn_measurement_method ' \f and \w scans with CCD ' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.034 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_k_min -33 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 26780 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_min 4.08 _diffrn_standards_decay_% 0.00 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.949 _exptl_absorpt_correction_T_max .850 _exptl_absorpt_correction_T_min .751 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_crystal_colour ' orange ' _exptl_crystal_density_diffrn 1.584 _exptl_crystal_density_meas ? _exptl_crystal_description ' block ' _exptl_crystal_F_000 1248.00 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.50 _refine_diff_density_min -0.54 _refine_ls_abs_structure_details 'Flack, 2692 Friedel-pairs' _refine_ls_abs_structure_Flack 0.350(13) _refine_ls_extinction_method None _refine_ls_goodness_of_fit_ref 1.0378 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 349 _refine_ls_number_reflns 4592 _refine_ls_R_factor_gt 0.0323 _refine_ls_shift/su_max 0.002408 _refine_ls_structure_factor_coef F _refine_ls_weighting_details ; Chebychev polynomial with 3 parameters, Carruthers & Watkin , 1979, 0.597 0.340 0.254 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.0386 _reflns_limit_h_max 11 _reflns_limit_h_min -11 _reflns_limit_k_max 33 _reflns_limit_k_min 0 _reflns_limit_l_max 14 _reflns_limit_l_min -14 _reflns_number_gt 4592 _reflns_number_total 5598 _reflns_threshold_expression >3.00\s(I) _[local]_cod_data_source_file ic040081q_1.cif _[local]_cod_data_source_block wgj2new2 _[local]_cod_cif_authors_sg_H-M 'C 1 c 1 ' _[local]_cod_chemical_formula_sum_orig ' C19 H29 Cl2 Co N4 O10 ' _cod_depositor_comments ; The following automatic conversions were performed: _chemical_melting_point value 'not measured' changed to '?' - value is undefined or not given. Automatic conversion script Id: cif_fix_values 1382 2010-08-28 14:56:29Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic ' changed to 'monoclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius ; _cod_database_code 4308356 loop_ _symmetry_equiv_pos_as_xyz x,y,z x+1/2,y+1/2,z x,-y,z+1/2 x+1/2,-y+1/2,z+1/2 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_occupancy _atom_site_adp_type Co1 co 0.50239(14) 0.366690(13) 0.50015(12) 0.0394 1.0000 Uani Cl1 cl 0.96636(17) 0.52483(3) 0.50895(13) 0.0603 1.0000 Uani Cl2 cl 0.91883(18) 0.24300(4) 0.51086(15) 0.0713 1.0000 Uani O1 o 0.9465(5) 0.41179(12) 0.7098(3) 0.0861 1.0000 Uani O2 o 1.0832(5) 0.55001(17) 0.4731(5) 0.1222 1.0000 Uani O3 o 0.8196(6) 0.5412(2) 0.4290(5) 0.1342 0.896(8) Uani O4 o 0.9797(6) 0.46985(13) 0.5061(6) 0.1106 0.896(8) Uani O5 o 0.9707(7) 0.5421(3) 0.6268(5) 0.1365 0.896(8) Uani O6 o 1.0720(5) 0.2378(3) 0.5811(8) 0.1942 1.0000 Uani O7 o 0.8616(7) 0.19761(17) 0.4374(4) 0.1323 1.0000 Uani O8 o 0.8880(6) 0.28805(18) 0.4339(5) 0.1442 1.0000 Uani O9 o 0.8263(5) 0.24578(17) 0.5903(3) 0.1022 1.0000 Uani O10 o 0.7096(3) 0.3488(1) 0.6099(2) 0.0556 1.0000 Uani O13 o 1.060(3) 0.4880(12) 0.594(3) 0.097(9) 0.104(8) Uiso O14 o 0.877(3) 0.4994(12) 0.400(2) 0.097(9) 0.104(8) Uiso O15 o 0.889(3) 0.558(1) 0.565(3) 0.097(9) 0.104(8) Uiso N4 n 0.4128(4) 0.35603(12) 0.6320(3) 0.0594 1.0000 Uani N7 n 0.4731(3) 0.28662(9) 0.4789(2) 0.0452 1.0000 Uani N10 n 0.2992(3) 0.3855(1) 0.3934(3) 0.0479 1.0000 Uani N13 n 0.5621(3) 0.3793(1) 0.3550(3) 0.0433 1.0000 Uani C1 c 0.5305(5) 0.44083(13) 0.5485(3) 0.0585 1.0000 Uani C2 c 0.4876(6) 0.44751(16) 0.6682(4) 0.0770 1.0000 Uani C3 c 0.4859(6) 0.39496(17) 0.7300(3) 0.0762 1.0000 Uani C5 c 0.4482(6) 0.30116(15) 0.6792(4) 0.0701 1.0000 Uani C6 c 0.4414(4) 0.26464(13) 0.5753(4) 0.0567 1.0000 Uani C8 c 0.4295(5) 0.47196(13) 0.4398(4) 0.0637 1.0000 Uani C9 c 0.2731(4) 0.44429(14) 0.3937(4) 0.0638 1.0000 Uani C11 c 0.2899(4) 0.36734(13) 0.2679(3) 0.0511 1.0000 Uani C12 c 0.4405(4) 0.38065(11) 0.2497(3) 0.0458 1.0000 Uani C14 c 0.2408(5) 0.36443(18) 0.5809(4) 0.0752 1.0000 Uani C15 c 0.1875(4) 0.35726(16) 0.4424(4) 0.0648 1.0000 Uani C16 c 0.4147(5) 0.21177(16) 0.5805(5) 0.0778 1.0000 Uani C17 c 0.4255(6) 0.18006(15) 0.4864(5) 0.0891 1.0000 Uani C18 c 0.4630(5) 0.20193(15) 0.3898(4) 0.0781 1.0000 Uani C19 c 0.4847(4) 0.25513(13) 0.3883(3) 0.0553 1.0000 Uani C20 c 0.4603(5) 0.39327(14) 0.1376(3) 0.0613 1.0000 Uani C21 c 0.6071(5) 0.40480(16) 0.1343(4) 0.0724 1.0000 Uani C22 c 0.7293(5) 0.40399(16) 0.2417(4) 0.0684 1.0000 Uani C23 c 0.7036(4) 0.39098(13) 0.3501(3) 0.0533 1.0000 Uani H1 h 0.764(3) 0.3749(12) 0.627(3) 0.0670 1.0000 Uiso H2 h 0.754(3) 0.3283(14) 0.578(3) 0.0670 1.0000 Uiso H3 h 0.957(6) 0.4301(18) 0.654(4) 0.1030 1.0000 Uiso H4 h 0.899(7) 0.4304(19) 0.747(5) 0.1030 1.0000 Uiso H11 h 0.6391(5) 0.45370(13) 0.5674(3) 0.0690 1.0000 Uiso H21 h 0.5655(6) 0.47080(16) 0.7261(4) 0.0934 1.0000 Uiso H22 h 0.3828(6) 0.46380(16) 0.6476(4) 0.0934 1.0000 Uiso H31 h 0.4247(6) 0.39771(17) 0.7884(3) 0.0942 1.0000 Uiso H32 h 0.5940(6) 0.38395(17) 0.7760(3) 0.0942 1.0000 Uiso H51 h 0.5541(6) 0.30003(15) 0.7409(4) 0.0892 1.0000 Uiso H52 h 0.3706(6) 0.28998(15) 0.7194(4) 0.0892 1.0000 Uiso H81 h 0.4157(5) 0.50841(13) 0.4662(4) 0.0757 1.0000 Uiso H82 h 0.4783(5) 0.47314(13) 0.3729(4) 0.0757 1.0000 Uiso H91 h 0.2111(4) 0.45272(14) 0.4494(4) 0.0767 1.0000 Uiso H92 h 0.2161(4) 0.45633(14) 0.3082(4) 0.0767 1.0000 Uiso H111 h 0.2033(4) 0.38549(13) 0.2047(3) 0.0587 1.0000 Uiso H112 h 0.2726(4) 0.32868(13) 0.2611(3) 0.0587 1.0000 Uiso H141 h 0.2153(5) 0.40069(18) 0.6010(4) 0.0975 1.0000 Uiso H142 h 0.1868(5) 0.33852(18) 0.6185(4) 0.0975 1.0000 Uiso H151 h 0.0814(4) 0.37216(16) 0.4056(4) 0.0807 1.0000 Uiso H152 h 0.1862(4) 0.31922(16) 0.4218(4) 0.0807 1.0000 Uiso H161 h 0.3879(5) 0.19664(16) 0.6517(5) 0.0926 1.0000 Uiso H171 h 0.4062(6) 0.14160(15) 0.4882(5) 0.0995 1.0000 Uiso H181 h 0.4743(5) 0.17946(15) 0.3217(4) 0.0853 1.0000 Uiso H191 h 0.5100(4) 0.27096(13) 0.3171(3) 0.0624 1.0000 Uiso H201 h 0.3698(5) 0.39400(14) 0.0605(3) 0.0729 1.0000 Uiso H211 h 0.6241(5) 0.41364(16) 0.0544(4) 0.0924 1.0000 Uiso H221 h 0.8359(5) 0.41277(16) 0.2410(4) 0.0876 1.0000 Uiso H231 h 0.7932(4) 0.39023(13) 0.4279(3) 0.0659 1.0000 Uiso 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 Co1 0.04474(17) 0.03846(15) 0.03611(14) -0.00055(17) 0.01448(11) 0.00389(17) Cl1 0.0675(6) 0.0517(4) 0.0652(5) -0.0087(4) 0.0258(4) 0.0016(3) Cl2 0.0701(6) 0.0606(5) 0.0912(6) 0.0082(4) 0.0367(5) 0.0124(4) O1 0.103(2) 0.0711(18) 0.0765(19) -0.0003(15) 0.0180(16) -0.0263(17) O2 0.119(3) 0.094(3) 0.181(5) -0.003(3) 0.088(3) -0.025(2) O3 0.094(3) 0.144(5) 0.125(4) 0.016(3) -0.021(3) 0.011(3) O4 0.129(4) 0.0526(16) 0.182(5) -0.008(3) 0.095(4) -0.002(2) O5 0.127(4) 0.200(6) 0.081(3) -0.052(3) 0.031(3) 0.028(4) O6 0.058(2) 0.167(5) 0.340(9) 0.070(6) 0.037(4) 0.035(3) O7 0.238(6) 0.083(3) 0.089(2) -0.0155(18) 0.069(3) 0.002(3) O8 0.137(4) 0.085(3) 0.216(5) 0.073(3) 0.065(4) 0.012(2) O9 0.093(2) 0.143(3) 0.0754(19) -0.005(2) 0.0328(17) 0.020(2) O10 0.0575(13) 0.0519(12) 0.0479(12) -0.005(1) 0.003(1) 0.006(1) N4 0.079(2) 0.0573(16) 0.0508(15) 0.0047(13) 0.0327(14) 0.0132(14) N7 0.0476(15) 0.0388(11) 0.0468(15) 0.0012(9) 0.0117(12) 0.0000(9) N10 0.0463(14) 0.0461(13) 0.0521(14) 0.004(1) 0.0167(11) 0.0068(11) N13 0.0452(13) 0.0404(12) 0.0455(13) 0.001(1) 0.016(1) 0.0012(9) C1 0.069(2) 0.0481(17) 0.0552(16) -0.0072(13) 0.0154(15) 0.0035(15) C2 0.106(3) 0.065(2) 0.063(2) -0.0212(18) 0.030(2) 0.010(2) C3 0.111(3) 0.076(3) 0.0477(19) -0.0099(16) 0.035(2) 0.011(2) C5 0.097(3) 0.067(2) 0.059(2) 0.0191(16) 0.043(2) 0.0119(19) C6 0.0546(18) 0.0505(17) 0.0657(19) 0.0164(15) 0.0201(15) 0.0002(14) C8 0.080(2) 0.0403(16) 0.069(2) 0.0021(14) 0.0212(18) 0.0091(15) C9 0.067(2) 0.0536(18) 0.071(2) 0.0062(15) 0.0222(16) 0.0216(15) C11 0.0475(15) 0.0518(16) 0.0474(14) 0.0006(12) 0.0055(12) 0.0030(13) C12 0.0539(16) 0.0426(14) 0.0394(13) 0.003(1) 0.0124(12) 0.0047(11) C14 0.075(2) 0.083(3) 0.085(3) 0.012(2) 0.051(2) 0.012(2) C15 0.0485(18) 0.071(2) 0.082(2) 0.0147(18) 0.0311(17) 0.0071(15) C16 0.073(2) 0.054(2) 0.105(3) 0.024(2) 0.025(2) -0.0012(17) C17 0.086(3) 0.0392(18) 0.124(4) 0.012(2) 0.007(3) -0.0045(18) C18 0.077(2) 0.0481(19) 0.088(3) -0.0179(19) -0.004(2) 0.0020(17) C19 0.0567(19) 0.0469(16) 0.0524(16) -0.0097(13) 0.0034(14) 0.0048(13) C20 0.083(2) 0.0554(19) 0.0436(16) 0.0071(13) 0.0179(15) 0.0084(16) C21 0.095(3) 0.074(2) 0.062(2) 0.0186(18) 0.044(2) 0.010(2) C22 0.070(2) 0.069(2) 0.080(2) 0.0161(19) 0.0431(19) 0.0032(18) C23 0.0507(16) 0.0545(17) 0.0595(18) 0.0062(13) 0.0245(14) 0.0010(13) loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7997 0.0030 International_Tables_Vol_IV_Table_2.2B 'Cl ' 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784 -9.5574 International_Tables_Vol_IV_Table_2.2B 'Co ' 0.2990 0.9730 12.2841 4.2791 7.3409 0.2784 4.0034 13.5359 2.3488 71.1692 1.0118 International_Tables_Vol_IV_Table_2.2B 'N ' 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 International_Tables_Vol_IV_Table_2.2B 'O ' 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 International_Tables_Vol_IV_Table_2.2B loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O10 . Co1 . N4 . 91.51(12) yes O10 . Co1 . N7 . 84.7(1) yes N4 . Co1 . N7 . 83.25(12) yes O10 . Co1 . N10 . 178.95(12) yes N4 . Co1 . N10 . 88.37(12) yes N7 . Co1 . N10 . 96.3(1) yes O10 . Co1 . N13 . 96.48(11) yes N4 . Co1 . N13 . 172.01(13) yes N7 . Co1 . N13 . 97.2(1) yes N10 . Co1 . N13 . 83.65(11) yes O10 . Co1 . C1 . 91.77(13) yes N4 . Co1 . C1 . 88.06(15) yes N7 . Co1 . C1 . 170.51(13) yes N10 . Co1 . C1 . 87.19(14) yes N13 . Co1 . C1 . 91.97(13) yes O2 . Cl1 . O3 . 108.7(3) yes O2 . Cl1 . O4 . 111.6(2) yes O3 . Cl1 . O4 . 110.3(4) yes O2 . Cl1 . O5 . 109.9(4) yes O3 . Cl1 . O5 . 105.1(3) yes O4 . Cl1 . O5 . 110.9(4) yes O2 . Cl1 . O13 . 98.7(12) yes O2 . Cl1 . O14 . 103.3(12) yes O13 . Cl1 . O14 . 110.5(15) yes O2 . Cl1 . O15 . 113.8(12) yes O13 . Cl1 . O15 . 111.9(15) yes O14 . Cl1 . O15 . 116.9(14) yes O6 . Cl2 . O7 . 112.2(4) yes O6 . Cl2 . O8 . 113.8(3) yes O7 . Cl2 . O8 . 109.2(3) yes O6 . Cl2 . O9 . 109.1(4) yes O7 . Cl2 . O9 . 103.7(3) yes O8 . Cl2 . O9 . 108.3(3) yes H3 . O1 . H4 . 106.0(27) no Co1 . O10 . H1 . 110.6(17) no Co1 . O10 . H2 . 112.0(16) no H1 . O10 . H2 . 106.5(24) no Co1 . N4 . C3 . 107.0(3) yes Co1 . N4 . C5 . 108.3(2) yes C3 . N4 . C5 . 111.1(3) yes Co1 . N4 . C14 . 108.6(2) yes C3 . N4 . C14 . 111.1(3) yes C5 . N4 . C14 . 110.6(3) yes Co1 . N7 . C6 . 111.7(2) yes Co1 . N7 . C19 . 130.1(2) yes C6 . N7 . C19 . 118.2(3) yes Co1 . N10 . C9 . 111.4(2) yes Co1 . N10 . C11 . 106.43(18) yes C9 . N10 . C11 . 110.5(3) yes Co1 . N10 . C15 . 105.8(2) yes C9 . N10 . C15 . 110.6(3) yes C11 . N10 . C15 . 112.0(3) yes Co1 . N13 . C12 . 113.3(2) yes Co1 . N13 . C23 . 127.5(2) yes C12 . N13 . C23 . 118.9(3) yes Co1 . C1 . C2 . 107.9(3) yes Co1 . C1 . C8 . 106.5(2) yes C2 . C1 . C8 . 114.2(3) yes Co1 . C1 . H11 . 114.16(12) no C2 . C1 . H11 . 106.4(2) no C8 . C1 . H11 . 107.9(2) no C1 . C2 . C3 . 110.9(3) yes C1 . C2 . H21 . 109.1(2) no C3 . C2 . H21 . 109.1(2) no C1 . C2 . H22 . 109.1(2) no C3 . C2 . H22 . 109.1(3) no H21 . C2 . H22 . 109.467 no N4 . C3 . C2 . 107.9(3) yes N4 . C3 . H31 . 109.9(2) no C2 . C3 . H31 . 109.9(2) no N4 . C3 . H32 . 109.9(2) no C2 . C3 . H32 . 109.9(3) no H31 . C3 . H32 . 109.467 no N4 . C5 . C6 . 110.3(3) yes N4 . C5 . H51 . 109.3(2) no C6 . C5 . H51 . 109.3(2) no N4 . C5 . H52 . 109.28(19) no C6 . C5 . H52 . 109.3(2) no H51 . C5 . H52 . 109.467 no N7 . C6 . C5 . 115.1(3) yes N7 . C6 . C16 . 122.1(4) yes C5 . C6 . C16 . 122.7(3) yes C1 . C8 . C9 . 107.3(3) yes C1 . C8 . H81 . 110.01(18) no C9 . C8 . H81 . 110.01(18) no C1 . C8 . H82 . 110.0(2) no C9 . C8 . H82 . 110.0(2) no H81 . C8 . H82 . 109.467 no N10 . C9 . C8 . 109.2(3) yes N10 . C9 . H91 . 109.54(18) no C8 . C9 . H91 . 109.5(2) no N10 . C9 . H92 . 109.54(18) no C8 . C9 . H92 . 109.5(2) no H91 . C9 . H92 . 109.467 no N10 . C11 . C12 . 106.9(2) yes N10 . C11 . H111 . 110.11(15) no C12 . C11 . H111 . 110.11(16) no N10 . C11 . H112 . 110.11(17) no C12 . C11 . H112 . 110.12(17) no H111 . C11 . H112 . 109.467 no N13 . C12 . C11 . 113.6(2) yes N13 . C12 . C20 . 121.2(3) yes C11 . C12 . C20 . 125.2(3) yes N4 . C14 . C15 . 109.8(3) yes N4 . C14 . H141 . 109.4(2) no C15 . C14 . H141 . 109.4(2) no N4 . C14 . H142 . 109.39(19) no C15 . C14 . H142 . 109.4(2) no H141 . C14 . H142 . 109.467 no N10 . C15 . C14 . 107.7(3) yes N10 . C15 . H151 . 109.92(17) no C14 . C15 . H151 . 109.9(2) no N10 . C15 . H152 . 109.92(19) no C14 . C15 . H152 . 109.9(2) no H151 . C15 . H152 . 109.467 no C6 . C16 . C17 . 119.1(4) yes C6 . C16 . H161 . 120.5(3) no C17 . C16 . H161 . 120.5(2) no C16 . C17 . C18 . 119.2(4) yes C16 . C17 . H171 . 120.4(2) no C18 . C17 . H171 . 120.4(3) no C17 . C18 . C19 . 119.1(4) yes C17 . C18 . H181 . 120.5(3) no C19 . C18 . H181 . 120.5(3) no N7 . C19 . C18 . 122.4(4) yes N7 . C19 . H191 . 118.8(2) no C18 . C19 . H191 . 118.8(3) no C12 . C20 . C21 . 119.0(3) yes C12 . C20 . H201 . 120.5(2) no C21 . C20 . H201 . 120.5(2) no C20 . C21 . C22 . 119.3(3) yes C20 . C21 . H211 . 120.3(2) no C22 . C21 . H211 . 120.3(2) no C21 . C22 . C23 . 119.3(3) yes C21 . C22 . H221 . 120.3(2) no C23 . C22 . H221 . 120.3(2) no N13 . C23 . C22 . 122.2(3) yes N13 . C23 . H231 . 118.92(18) no C22 . C23 . H231 . 118.9(2) no loop_ _geom_bond_atom_site_label_D _geom_bond_atom_site_label_H _geom_contact_atom_site_label_a _geom_bond_distance_DH _geom_contact_distance_HA _geom_contact_distance_DA _geom_angle_DHA _geom_contact_site_symmetry_A O1 H3 O13 0.82(5) 1.99(6) 2.74(3) 151(4) . O10 H1 O1 0.82(3) 1.89(3) 2.646(4) 154(3) . O10 H2 O9 0.82(4) 2.20(4) 2.876(5) 140(3) . O1 H3 O4 0.82(5) 2.04(5) 2.860(7) 175(4) . loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Co1 . O10 . 1.963(2) yes Co1 . N4 . 1.949(3) yes Co1 . N7 . 2.069(2) yes Co1 . N10 . 1.930(3) yes Co1 . N13 . 1.932(3) yes Co1 . C1 . 1.968(3) yes Cl1 . O2 . 1.412(4) yes Cl1 . O3 . 1.424(4) yes Cl1 . O4 . 1.412(3) yes Cl1 . O5 . 1.408(4) yes Cl1 . O13 . 1.427(18) yes Cl1 . O14 . 1.413(18) yes Cl1 . O15 . 1.374(18) yes Cl2 . O6 . 1.379(5) yes Cl2 . O7 . 1.431(4) yes Cl2 . O8 . 1.423(4) yes Cl2 . O9 . 1.424(4) yes O1 . H3 . 0.83(4) no O1 . H4 . 0.84(4) no O10 . H1 . 0.82(3) no O10 . H2 . 0.81(3) no N4 . C3 . 1.490(5) yes N4 . C5 . 1.501(5) yes N4 . C14 . 1.506(5) yes N7 . C6 . 1.348(4) yes N7 . C19 . 1.344(4) yes N10 . C9 . 1.521(4) yes N10 . C11 . 1.486(4) yes N10 . C15 . 1.495(4) yes N13 . C12 . 1.355(4) yes N13 . C23 . 1.343(4) yes C1 . C2 . 1.549(5) yes C1 . C8 . 1.518(5) yes C1 . H11 . 1.000 no C2 . C3 . 1.521(6) yes C2 . H21 . 1.000 no C2 . H22 . 1.000 no C3 . H31 . 1.000 no C3 . H32 . 1.000 no C5 . C6 . 1.498(5) yes C5 . H51 . 1.000 no C5 . H52 . 1.000 no C6 . C16 . 1.378(5) yes C8 . C9 . 1.528(6) yes C8 . H81 . 1.000 no C8 . H82 . 1.000 no C9 . H91 . 1.000 no C9 . H92 . 1.000 no C11 . C12 . 1.492(5) yes C11 . H111 . 1.000 no C11 . H112 . 1.000 no C12 . C20 . 1.390(4) yes C14 . C15 . 1.515(6) yes C14 . H141 . 1.000 no C14 . H142 . 1.000 no C15 . H151 . 1.000 no C15 . H152 . 1.000 no C16 . C17 . 1.377(7) yes C16 . H161 . 1.000 no C17 . C18 . 1.375(7) yes C17 . H171 . 1.000 no C18 . C19 . 1.375(5) yes C18 . H181 . 1.000 no C19 . H191 . 1.000 no C20 . C21 . 1.382(6) yes C20 . H201 . 1.000 no C21 . C22 . 1.373(6) yes C21 . H211 . 1.000 no C22 . C23 . 1.375(5) yes C22 . H221 . 1.000 no C23 . H231 . 1.000 no 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 O1 O10 2.646(4) . . no O1 O13 2.74(3) . . no O1 O4 2.860(7) . . no O1 O2 3.035(6) . 3_565 no O1 O3 3.304(7) . 3_565 no O1 O14 3.34(3) . 3_565 no O1 O5 3.490(8) . . no O1 C18 3.539(5) . 4 no O2 C9 3.482(6) . 1_655 no O3 C2 3.526(6) . 3_564 no O3 C3 3.566(6) . 3_564 no O4 C23 3.278(5) . . no O4 C9 3.379(8) . 1_655 no O4 C14 3.517(6) . 1_655 no O4 C22 3.582(6) . . no O5 C22 3.210(9) . 3_565 no O5 C9 3.423(6) . 3_665 no O6 C16 3.197(7) . 1_655 no O6 C6 3.458(7) . 1_655 no O6 C14 3.585(9) . 1_655 no O7 C20 3.186(5) . 4 no O7 C5 3.292(8) . 4_554 no O7 C18 3.502(8) . . no O8 C23 3.106(6) . . no O8 C15 3.229(7) . 1_655 no O8 O10 3.345(7) . . no O9 O10 2.876(5) . . no O9 N7 3.238(5) . . no O9 C19 3.247(5) . . no O9 C19 3.256(4) . 4 no O9 C6 3.492(6) . . no O9 C18 3.519(5) . 4 no O9 C18 3.561(5) . . no O10 C18 3.549(4) . 4 no O13 C14 3.59(3) . 1_655 no O14 C22 3.08(3) . . no O14 C23 3.15(3) . . no O15 C22 3.00(4) . 3_565 no O15 C21 3.07(3) . 3_565 no O15 C17 3.29(3) . 2 no 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag Co1 N4 C3 C2 . . . . 45.1(4) no Co1 N4 C5 C6 . . . . -36.7(4) no Co1 N4 C14 C15 . . . . 21.9(4) no Co1 N7 C6 C5 . . . . -5.2(4) no Co1 N7 C6 C16 . . . . 178.9(3) no Co1 N7 C19 C18 . . . . 179.2(3) no Co1 N10 C9 C8 . . . . 20.0(4) no Co1 N10 C11 C12 . . . . -42.3(3) no Co1 N10 C15 C14 . . . . 45.6(3) no Co1 N13 C12 C11 . . . . -5.2(3) no Co1 N13 C12 C20 . . . . 175.0(2) no Co1 N13 C23 C22 . . . . -173.7(3) no Co1 C1 C2 C3 . . . . 17.1(4) no Co1 C1 C8 C9 . . . . 44.7(4) no O10 Co1 N4 C3 . . . . 62.3(2) no O10 Co1 N4 C5 . . . . -57.5(2) no O10 Co1 N4 C14 . . . . -177.7(2) no O10 Co1 N7 C6 . . . . 79.2(2) no O10 Co1 N7 C19 . . . . -99.0(3) no O10 Co1 N13 C12 . . . . 164.8(2) no O10 Co1 N13 C23 . . . . -21.5(3) no O10 Co1 C1 C2 . . . . -84.7(3) no O10 Co1 C1 C8 . . . . 152.3(3) no O13 Cl1 O3 O14 . . . . -65(3) no O13 Cl1 O3 O15 . . . . 93(3) no O13 Cl1 O4 O14 . . . . -177(2) no O13 Cl1 O5 O15 . . . . -163(2) no O13 O4 Cl1 O14 . . . . 177(2) no O13 O4 Cl1 O15 . . . . -80(2) no O13 O5 Cl1 O14 . . . . 103(2) no O13 O5 Cl1 O15 . . . . 163(2) no O14 Cl1 O3 O15 . . . . 159(2) no O14 Cl1 O5 O15 . . . . -60(3) no O14 O3 Cl1 O15 . . . . -159(2) no O14 O4 Cl1 O15 . . . . 103(2) no N4 Co1 N7 C6 . . . . -13.0(2) no N4 Co1 N7 C19 . . . . 168.8(3) no N4 Co1 N10 C9 . . . . 92.6(3) no N4 Co1 N10 C11 . . . . -146.9(2) no N4 Co1 N10 C15 . . . . -27.5(2) no N4 Co1 C1 C2 . . . . 6.8(3) no N4 Co1 C1 C8 . . . . -116.2(3) no N4 C3 C2 C1 . . . . -40.9(5) no N4 C5 C6 N7 . . . . 27.5(5) no N4 C5 C6 C16 . . . . -156.6(4) no N4 C14 C15 N10 . . . . -44.7(4) no N7 Co1 N4 C3 . . . . 146.7(3) no N7 Co1 N4 C5 . . . . 26.9(2) no N7 Co1 N4 C14 . . . . -93.2(2) no N7 Co1 N10 C9 . . . . 175.6(3) no N7 Co1 N10 C11 . . . . -63.9(2) no N7 Co1 N10 C15 . . . . 55.5(2) no N7 Co1 N13 C12 . . . . 79.4(2) no N7 Co1 N13 C23 . . . . -106.9(3) no N7 C6 C16 C17 . . . . 2.1(6) no N7 C19 C18 C17 . . . . 1.1(6) no N10 Co1 N4 C3 . . . . -116.7(3) no N10 Co1 N4 C5 . . . . 123.5(2) no N10 Co1 N4 C14 . . . . 3.3(3) no N10 Co1 N7 C6 . . . . -100.6(2) no N10 Co1 N7 C19 . . . . 81.2(3) no N10 Co1 N13 C12 . . . . -16.2(2) no N10 Co1 N13 C23 . . . . 157.5(3) no N10 Co1 C1 C2 . . . . 95.2(3) no N10 Co1 C1 C8 . . . . -27.8(3) no N10 C9 C8 C1 . . . . -42.1(5) no N10 C11 C12 N13 . . . . 31.5(3) no N10 C11 C12 C20 . . . . -148.7(3) no N13 Co1 N7 C6 . . . . 175.0(2) no N13 Co1 N7 C19 . . . . -3.1(3) no N13 Co1 N10 C9 . . . . -87.8(3) no N13 Co1 N10 C11 . . . . 32.7(2) no N13 Co1 N10 C15 . . . . 152.0(2) no N13 Co1 C1 C2 . . . . 178.8(3) no N13 Co1 C1 C8 . . . . 55.8(3) no N13 C12 C20 C21 . . . . -0.2(5) no N13 C23 C22 C21 . . . . -0.5(6) no C1 Co1 N4 C3 . . . . -29.4(3) no C1 Co1 N4 C5 . . . . -149.2(3) no C1 Co1 N4 C14 . . . . 90.6(3) no C1 Co1 N10 C9 . . . . 4.5(3) no C1 Co1 N10 C11 . . . . 125.0(2) no C1 Co1 N10 C15 . . . . -115.7(3) no C1 Co1 N13 C12 . . . . -103.2(2) no C1 Co1 N13 C23 . . . . 70.5(3) no C2 C1 C8 C9 . . . . -74.3(4) no C2 C3 N4 C5 . . . . 163.1(4) no C2 C3 N4 C14 . . . . -73.3(5) no C3 N4 C5 C6 . . . . -153.9(4) no C3 N4 C14 C15 . . . . 139.3(4) no C3 C2 C1 C8 . . . . 135.3(4) no C5 N4 C14 C15 . . . . -96.9(4) no C5 C6 N7 C19 . . . . 173.3(3) no C5 C6 C16 C17 . . . . -173.6(4) no C6 N7 C19 C18 . . . . 1.1(5) no C6 C5 N4 C14 . . . . 82.3(5) no C6 C16 C17 C18 . . . . 0.2(6) no C8 C9 N10 C11 . . . . -98.1(4) no C8 C9 N10 C15 . . . . 137.4(3) no C9 N10 C11 C12 . . . . 78.7(3) no C9 N10 C15 C14 . . . . -75.1(4) no C11 N10 C15 C14 . . . . 161.3(3) no C11 C12 N13 C23 . . . . -179.5(3) no C11 C12 C20 C21 . . . . -180.0(3) no C12 N13 C23 C22 . . . . -0.4(5) no C12 C11 N10 C15 . . . . -157.6(3) no C12 C20 C21 C22 . . . . -0.6(6) no C16 C6 N7 C19 . . . . -2.7(5) no C16 C17 C18 C19 . . . . -1.7(6) no C20 C12 N13 C23 . . . . 0.7(5) no C20 C21 C22 C23 . . . . 0.9(6) no _journal_paper_doi 10.1021/ic040081q