# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Melanie Pilkington' _publ_contact_author_address ; Chemistry Brock University St. Catharines Ontario L2S3A1 CANADA ; _publ_contact_author_email MPILKINGTON@BROCKU.CA _publ_section_title ; Acid Catalyzed Rearrangment of a 2,2'-Bipyridine Schiff-Base Ligand to a Quaterpyridine-Type Complex ; loop_ _publ_author_name 'Melanie Pilkington' 'J. Halfpenny' 'Stuart T. Onions' 'Helen Stoeckli-Evans' 'J. Wallis' ; Jian Wang ; data_rearrangedligand _database_code_depnum_ccdc_archive 'CCDC 644440' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H14 N5, Cl' _chemical_formula_sum 'C16 H14 Cl N5' _chemical_formula_weight 311.77 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.9931(15) _cell_length_b 12.4406(14) _cell_length_c 9.5280(11) _cell_angle_alpha 90.00 _cell_angle_beta 109.248(7) _cell_angle_gamma 90.00 _cell_volume 1454.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.280 _exptl_crystal_size_mid 0.220 _exptl_crystal_size_min 0.065 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.424 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.266 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.920 _exptl_absorpt_correction_T_max 0.983 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_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. ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice and scans' _diffrn_reflns_number 15114 _diffrn_reflns_av_R_equivalents 0.0447 _diffrn_reflns_av_sigmaI/netI 0.0437 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 30.61 _reflns_number_total 4458 _reflns_number_gt 3731 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otinowinski & Minor 1997)' _computing_data_reduction 'HKL Scalepack (Otinowinski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0545P)^2^+0.4411P] 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 4458 _refine_ls_number_parameters 255 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0480 _refine_ls_R_factor_gt 0.0385 _refine_ls_wR_factor_ref 0.1059 _refine_ls_wR_factor_gt 0.0991 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.75474(2) 0.18639(2) 0.63162(3) 0.01589(9) Uani 1 1 d . . . N1 N 0.65866(9) 0.65150(9) 0.73978(11) 0.0164(2) Uani 1 1 d . . . N2 N 0.78941(9) 0.43684(9) 0.59633(11) 0.0149(2) Uani 1 1 d . . . N3 N 0.65342(8) 0.52438(8) 0.39351(11) 0.01253(19) Uani 1 1 d . . . N4 N 0.48139(10) 0.70870(10) 0.51247(14) 0.0230(2) Uani 1 1 d . . . N5 N 0.81769(8) 0.61795(9) 0.30968(11) 0.0168(2) Uani 1 1 d . . . C1 C 0.70477(11) 0.63529(11) 0.88551(14) 0.0195(3) Uani 1 1 d . . . C2 C 0.77522(11) 0.55031(11) 0.94527(14) 0.0201(3) Uani 1 1 d . . . C3 C 0.80422(11) 0.48198(11) 0.85052(13) 0.0183(2) Uani 1 1 d . . . C4 C 0.76119(10) 0.49970(10) 0.69744(13) 0.0141(2) Uani 1 1 d . . . C5 C 0.68467(9) 0.58330(10) 0.64617(12) 0.0130(2) Uani 1 1 d . . . C6 C 0.61975(9) 0.58718(9) 0.48773(13) 0.0125(2) Uani 1 1 d . . . C7 C 0.51919(10) 0.64290(10) 0.42858(13) 0.0147(2) Uani 1 1 d . . . C8 C 0.45857(10) 0.62654(10) 0.27721(14) 0.0159(2) Uani 1 1 d . . . C9 C 0.49560(10) 0.55900(11) 0.19040(13) 0.0172(2) Uani 1 1 d . . . C10 C 0.59535(10) 0.50795(10) 0.24978(13) 0.0159(2) Uani 1 1 d . . . C11 C 0.76707(10) 0.47935(10) 0.45116(13) 0.0131(2) Uani 1 1 d . . . C12 C 0.84442(9) 0.56979(9) 0.44239(12) 0.0125(2) Uani 1 1 d . . . C13 C 0.93714(10) 0.59601(10) 0.56063(13) 0.0153(2) Uani 1 1 d . . . C14 C 1.00458(10) 0.67722(11) 0.54031(14) 0.0176(2) Uani 1 1 d . . . C15 C 0.97777(10) 0.72781(11) 0.40377(15) 0.0190(2) Uani 1 1 d . . . C16 C 0.88401(11) 0.69534(11) 0.29194(15) 0.0197(3) Uani 1 1 d . . . H1 H 0.8538(15) 0.4198(15) 0.889(2) 0.027(5) Uiso 1 1 d . . . H2 H 0.8021(14) 0.5398(14) 1.055(2) 0.025(4) Uiso 1 1 d . . . H3 H 0.6855(16) 0.6850(15) 0.951(2) 0.031(5) Uiso 1 1 d . . . H4 H 0.5201(16) 0.7194(16) 0.605(2) 0.032(5) Uiso 1 1 d . . . H5 H 0.4156(16) 0.7337(16) 0.474(2) 0.031(5) Uiso 1 1 d . . . H6 H 0.3905(15) 0.6621(15) 0.235(2) 0.027(5) Uiso 1 1 d . . . H7 H 0.4519(14) 0.5500(14) 0.0872(19) 0.020(4) Uiso 1 1 d . . . H8 H 0.6280(14) 0.4657(14) 0.1962(19) 0.022(4) Uiso 1 1 d . . . H9 H 0.8644(14) 0.7275(15) 0.196(2) 0.026(4) Uiso 1 1 d . . . H10 H 1.0213(15) 0.7847(15) 0.386(2) 0.027(4) Uiso 1 1 d . . . H11 H 1.0689(16) 0.6953(14) 0.620(2) 0.030(5) Uiso 1 1 d . . . H12 H 0.9549(14) 0.5601(14) 0.6521(19) 0.023(4) Uiso 1 1 d . . . H13 H 0.7863(15) 0.3679(16) 0.604(2) 0.027(5) Uiso 1 1 d . . . H14 H 0.7702(13) 0.4222(14) 0.3864(18) 0.018(4) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.01627(15) 0.01362(14) 0.01662(14) 0.00247(10) 0.00385(10) 0.00085(10) N1 0.0183(5) 0.0167(5) 0.0151(5) -0.0030(4) 0.0068(4) -0.0007(4) N2 0.0200(5) 0.0112(5) 0.0134(4) 0.0006(4) 0.0056(4) 0.0013(4) N3 0.0134(4) 0.0119(4) 0.0125(4) -0.0009(3) 0.0045(3) -0.0012(3) N4 0.0183(5) 0.0288(6) 0.0201(5) -0.0048(5) 0.0038(4) 0.0092(5) N5 0.0163(5) 0.0202(5) 0.0137(4) 0.0009(4) 0.0048(4) -0.0019(4) C1 0.0239(6) 0.0209(6) 0.0148(5) -0.0041(5) 0.0080(5) -0.0030(5) C2 0.0249(6) 0.0230(6) 0.0119(5) 0.0004(5) 0.0055(5) -0.0042(5) C3 0.0214(6) 0.0180(6) 0.0142(5) 0.0030(4) 0.0041(5) 0.0001(5) C4 0.0170(5) 0.0128(5) 0.0128(5) 0.0006(4) 0.0055(4) -0.0017(4) C5 0.0144(5) 0.0134(5) 0.0114(5) -0.0006(4) 0.0046(4) -0.0012(4) C6 0.0127(5) 0.0125(5) 0.0126(5) -0.0002(4) 0.0045(4) -0.0010(4) C7 0.0143(5) 0.0142(5) 0.0160(5) 0.0008(4) 0.0055(4) -0.0006(4) C8 0.0132(5) 0.0171(6) 0.0166(5) 0.0034(4) 0.0038(4) -0.0010(4) C9 0.0164(6) 0.0207(6) 0.0129(5) 0.0007(4) 0.0028(4) -0.0024(5) C10 0.0178(6) 0.0168(6) 0.0130(5) -0.0022(4) 0.0047(4) -0.0025(4) C11 0.0137(5) 0.0128(5) 0.0130(5) -0.0008(4) 0.0046(4) 0.0013(4) C12 0.0131(5) 0.0130(5) 0.0124(5) -0.0015(4) 0.0054(4) 0.0009(4) C13 0.0143(5) 0.0173(6) 0.0139(5) -0.0022(4) 0.0040(4) 0.0020(4) C14 0.0128(5) 0.0203(6) 0.0185(5) -0.0050(5) 0.0038(4) -0.0006(4) C15 0.0165(6) 0.0193(6) 0.0229(6) -0.0028(5) 0.0090(5) -0.0036(5) C16 0.0198(6) 0.0221(6) 0.0174(6) 0.0026(5) 0.0063(5) -0.0035(5) _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 N1 C1 1.3338(16) . ? N1 C5 1.3522(15) . ? N2 C4 1.3810(15) . ? N2 C11 1.4185(15) . ? N2 H13 0.86(2) . ? N3 C10 1.3436(15) . ? N3 C6 1.3663(15) . ? N3 C11 1.5038(15) . ? N4 C7 1.3449(17) . ? N4 H4 0.87(2) . ? N4 H5 0.87(2) . ? N5 C12 1.3375(15) . ? N5 C16 1.3395(16) . ? C1 C2 1.391(2) . ? C1 H3 0.969(19) . ? C2 C3 1.3798(19) . ? C2 H2 0.995(17) . ? C3 C4 1.3967(16) . ? C3 H1 0.995(18) . ? C4 C5 1.4101(17) . ? C5 C6 1.4674(16) . ? C6 C7 1.4212(17) . ? C7 C8 1.4117(17) . ? C8 C9 1.3725(18) . ? C8 H6 0.951(19) . ? C9 C10 1.3856(18) . ? C9 H7 0.966(17) . ? C10 H8 0.928(18) . ? C11 C12 1.5292(17) . ? C11 H14 0.951(17) . ? C12 C13 1.3900(16) . ? C13 C14 1.3920(18) . ? C13 H12 0.938(17) . ? C14 C15 1.3825(19) . ? C14 H11 0.954(19) . ? C15 C16 1.3881(18) . ? C15 H10 0.957(19) . ? C16 H9 0.952(18) . ? 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 C1 N1 C5 117.88(11) . . ? C4 N2 C11 116.94(10) . . ? C4 N2 H13 118.3(12) . . ? C11 N2 H13 116.8(12) . . ? C10 N3 C6 124.25(11) . . ? C10 N3 C11 118.00(10) . . ? C6 N3 C11 117.49(9) . . ? C7 N4 H4 119.5(13) . . ? C7 N4 H5 118.0(13) . . ? H4 N4 H5 122.2(18) . . ? C12 N5 C16 117.64(11) . . ? N1 C1 C2 123.36(12) . . ? N1 C1 H3 116.8(11) . . ? C2 C1 H3 119.8(11) . . ? C3 C2 C1 119.02(11) . . ? C3 C2 H2 121.9(10) . . ? C1 C2 H2 119.0(10) . . ? C2 C3 C4 118.97(12) . . ? C2 C3 H1 121.6(11) . . ? C4 C3 H1 119.4(11) . . ? N2 C4 C3 122.15(11) . . ? N2 C4 C5 119.67(10) . . ? C3 C4 C5 118.16(11) . . ? N1 C5 C4 122.36(10) . . ? N1 C5 C6 118.29(11) . . ? C4 C5 C6 118.77(10) . . ? N3 C6 C7 118.03(10) . . ? N3 C6 C5 117.20(10) . . ? C7 C6 C5 124.44(10) . . ? N4 C7 C8 120.32(12) . . ? N4 C7 C6 121.96(11) . . ? C8 C7 C6 117.72(11) . . ? C9 C8 C7 121.04(11) . . ? C9 C8 H6 119.7(11) . . ? C7 C8 H6 119.3(11) . . ? C8 C9 C10 120.06(11) . . ? C8 C9 H7 118.6(10) . . ? C10 C9 H7 121.3(10) . . ? N3 C10 C9 118.81(11) . . ? N3 C10 H8 116.3(10) . . ? C9 C10 H8 124.8(10) . . ? N2 C11 N3 110.84(10) . . ? N2 C11 C12 113.62(10) . . ? N3 C11 C12 106.85(9) . . ? N2 C11 H14 108.4(10) . . ? N3 C11 H14 106.7(10) . . ? C12 C11 H14 110.2(10) . . ? N5 C12 C13 123.14(11) . . ? N5 C12 C11 114.25(10) . . ? C13 C12 C11 122.55(11) . . ? C12 C13 C14 118.35(12) . . ? C12 C13 H12 121.5(11) . . ? C14 C13 H12 120.1(11) . . ? C15 C14 C13 119.10(11) . . ? C15 C14 H11 121.8(11) . . ? C13 C14 H11 119.0(11) . . ? C14 C15 C16 118.36(12) . . ? C14 C15 H10 121.8(11) . . ? C16 C15 H10 119.8(11) . . ? N5 C16 C15 123.41(12) . . ? N5 C16 H9 116.3(11) . . ? C15 C16 H9 120.3(11) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 30.61 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.468 _refine_diff_density_min -0.242 _refine_diff_density_rms 0.065 # Attachment 'mp2.cif' data_Coquaterpy _database_code_depnum_ccdc_archive 'CCDC 644441' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H19 Co N7 O, 2(Cl O4)' _chemical_formula_sum 'C24 H19 Cl2 Co N7 O9' _chemical_formula_weight 679.29 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' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C c' _symmetry_space_group_name_Hall 'C -2yc' loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 x,-y,1/2+z 3 1/2+x,1/2+y,z 4 1/2+x,1/2-y,1/2+z _cell_length_a 14.311(2) _cell_length_b 13.4071(16) _cell_length_c 14.598(2) _cell_angle_alpha 90.00 _cell_angle_beta 103.464(17) _cell_angle_gamma 90.00 _cell_volume 2723.9(7) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3908 _cell_measurement_theta_min 2.05 _cell_measurement_theta_max 25.70 _exptl_crystal_description rod _exptl_crystal_colour brown _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.656 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1380 _exptl_absorpt_coefficient_mu 0.893 _exptl_absorpt_correction_type refdelf _exptl_absorpt_correction_T_min 0.619 _exptl_absorpt_correction_T_max 0.887 _exptl_absorpt_process_details 'DIFrefABS in PLATON (Spek, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE IPDS' _diffrn_measurement_method 'phi rotation' _diffrn_detector_area_resol_mean 0.81\%A _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 8587 _diffrn_reflns_av_R_equivalents 0.0804 _diffrn_reflns_av_sigmaI/netI 0.1666 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 26.03 _reflns_number_total 4930 _reflns_number_gt 2656 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'EXPOSE (Stoe IPDS Software, 2000)' _computing_cell_refinement 'CELL (Stoe IPDS Software, 2000)' _computing_data_reduction 'INTEGRATE (Stoe IPDS Software, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material SHELXL-97 _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^)+(0.0610P)^2^] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.08(3) _refine_ls_number_reflns 4930 _refine_ls_number_parameters 377 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.1222 _refine_ls_R_factor_gt 0.0552 _refine_ls_wR_factor_ref 0.1351 _refine_ls_wR_factor_gt 0.1157 _refine_ls_goodness_of_fit_ref 0.851 _refine_ls_restrained_S_all 0.850 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean <0.001 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags Co1 Co Uani -0.00561(7) 0.36454(7) 0.25253(8) 1.000 0.0308(3) . . O1W O Uani -0.1399(4) 0.3541(5) 0.2933(4) 1.000 0.039(2) . . N1 N Uani -0.0687(5) 0.2803(5) 0.1278(5) 1.000 0.038(3) . . N2 N Uani -0.0586(5) 0.4756(5) 0.1511(6) 1.000 0.037(3) . . N3 N Uani 0.0270(4) 0.5020(5) 0.3227(5) 1.000 0.027(2) . . N4 N Uani 0.0599(5) 0.3230(5) 0.3961(5) 1.000 0.029(2) . . N5 N Uani 0.1278(5) 0.3586(5) 0.2181(5) 1.000 0.037(3) . . N6 N Uani 0.0137(5) 0.7680(5) 0.2755(5) 1.000 0.046(3) . . N7 N Uani 0.0974(5) 0.5802(6) 0.4680(6) 1.000 0.040(3) . . C1 C Uani -0.0715(6) 0.1837(7) 0.1199(7) 1.000 0.045(3) . . C2 C Uani -0.1132(6) 0.1353(8) 0.0389(7) 1.000 0.046(3) . . C3 C Uani -0.1554(6) 0.1897(7) -0.0373(7) 1.000 0.042(3) . . C4 C Uani -0.1582(6) 0.2908(8) -0.0351(7) 1.000 0.046(4) . . C5 C Uani -0.1121(6) 0.3384(6) 0.0504(7) 1.000 0.037(3) . . C6 C Uani -0.1051(5) 0.4472(7) 0.0651(6) 1.000 0.033(3) . . C7 C Uani -0.1447(6) 0.5149(7) -0.0040(6) 1.000 0.039(3) . . C8 C Uani -0.1314(6) 0.6156(8) 0.0200(7) 1.000 0.042(3) . . C9 C Uani -0.0814(6) 0.6451(7) 0.1040(7) 1.000 0.035(3) . . C10 C Uani -0.0457(5) 0.5734(6) 0.1744(6) 1.000 0.034(3) . . C11 C Uani 0.0053(6) 0.5887(6) 0.2748(6) 1.000 0.033(3) . . C12 C Uani 0.0344(6) 0.6795(6) 0.3258(7) 1.000 0.039(3) . . C13 C Uani 0.0412(6) 0.8474(6) 0.3269(7) 1.000 0.047(3) . . C14 C Uani 0.0888(6) 0.8484(7) 0.4208(7) 1.000 0.047(3) . . C15 C Uani 0.1075(6) 0.7595(7) 0.4692(7) 1.000 0.050(4) . . C16 C Uani 0.0802(6) 0.6701(7) 0.4185(7) 1.000 0.035(3) . . C17 C Uani 0.0714(5) 0.5008(6) 0.4133(6) 1.000 0.028(3) . . C18 C Uani 0.0895(6) 0.3999(7) 0.4556(7) 1.000 0.037(3) . . C19 C Uani 0.1331(5) 0.3844(8) 0.5498(6) 1.000 0.042(4) . . C20 C Uani 0.1449(6) 0.2888(8) 0.5848(8) 1.000 0.047(4) . . C21 C Uani 0.1138(6) 0.2095(8) 0.5213(8) 1.000 0.049(4) . . C22 C Uani 0.0749(6) 0.2291(7) 0.4296(7) 1.000 0.043(3) . . C23 C Uani 0.2004(7) 0.3642(7) 0.1972(6) 1.000 0.045(3) . . C24 C Uani 0.2903(6) 0.3742(8) 0.1721(7) 1.000 0.060(4) . . Cl1 Cl Uani 0.32100(16) 0.59744(16) 0.36211(17) 1.000 0.0449(8) . . O11 O Uani 0.2543(4) 0.5171(5) 0.3572(6) 1.000 0.070(3) . . O12 O Uani 0.2742(7) 0.6769(7) 0.3130(8) 1.000 0.135(5) . . O13 O Uani 0.3514(6) 0.6306(7) 0.4574(5) 1.000 0.097(4) . . O14 O Uani 0.3990(5) 0.5711(7) 0.3273(7) 1.000 0.113(4) . . Cl2 Cl Uani 0.19189(15) 0.05962(17) 0.22009(16) 1.000 0.0433(8) . . O21 O Uani 0.1486(8) 0.1043(10) 0.1367(9) 1.000 0.141(3) . . O22 O Uani 0.2828(8) 0.0914(8) 0.2634(8) 1.000 0.141(3) . . O23 O Uani 0.1377(7) 0.0685(8) 0.2861(8) 1.000 0.141(3) . . O24 O Uani 0.2038(8) -0.0362(9) 0.1886(8) 1.000 0.141(3) . . H1WA H Uiso -0.179(5) 0.310(5) 0.304(7) 1.000 0.0580 . . H1A H Uiso -0.04300 0.14490 0.17360 1.000 0.0540 calc R H1WB H Uiso -0.182(5) 0.399(5) 0.273(6) 1.000 0.0580 . . H2A H Uiso -0.11270 0.06450 0.03600 1.000 0.0550 calc R H3A H Uiso -0.18390 0.15620 -0.09430 1.000 0.0510 calc R H4A H Uiso -0.18970 0.32830 -0.08870 1.000 0.0550 calc R H7A H Uiso -0.17930 0.49420 -0.06470 1.000 0.0470 calc R H8A H Uiso -0.15880 0.66460 -0.02530 1.000 0.0500 calc R H9A H Uiso -0.06980 0.71400 0.11680 1.000 0.0420 calc R H13A H Uiso 0.02710 0.91020 0.29680 1.000 0.0560 calc R H14A H Uiso 0.10850 0.90980 0.45180 1.000 0.0570 calc R H15A H Uiso 0.13780 0.75830 0.53440 1.000 0.0600 calc R H19A H Uiso 0.15480 0.43960 0.58990 1.000 0.0500 calc R H20A H Uiso 0.17290 0.27660 0.64950 1.000 0.0570 calc R H21A H Uiso 0.12030 0.14250 0.54310 1.000 0.0580 calc R H22A H Uiso 0.05750 0.17490 0.38710 1.000 0.0520 calc R H24A H Uiso 0.27980 0.37590 0.10330 1.000 0.0900 calc R H24B H Uiso 0.33150 0.31730 0.19690 1.000 0.0900 calc R H24C H Uiso 0.32160 0.43610 0.19870 1.000 0.0900 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 Co1 0.0319(5) 0.0302(6) 0.0287(7) 0.0001(6) 0.0038(4) -0.0004(6) O1W 0.033(3) 0.045(4) 0.041(4) 0.007(3) 0.015(3) -0.001(3) N1 0.041(4) 0.033(5) 0.036(5) -0.011(4) 0.002(3) -0.002(3) N2 0.035(4) 0.036(5) 0.039(5) 0.007(4) 0.006(3) 0.006(3) N3 0.023(3) 0.026(4) 0.034(5) -0.002(3) 0.011(3) 0.001(3) N4 0.035(4) 0.026(4) 0.026(4) -0.002(3) 0.008(3) -0.001(3) N5 0.045(5) 0.037(4) 0.030(5) -0.001(3) 0.014(4) 0.000(3) N6 0.053(5) 0.033(4) 0.047(6) 0.006(4) -0.001(4) -0.005(3) N7 0.037(4) 0.041(5) 0.039(5) -0.013(4) 0.004(3) 0.005(4) C1 0.048(5) 0.033(5) 0.044(7) -0.005(5) -0.007(5) -0.002(4) C2 0.061(6) 0.032(5) 0.044(7) -0.022(5) 0.010(5) -0.012(5) C3 0.062(6) 0.036(5) 0.024(6) -0.014(5) 0.000(5) -0.008(4) C4 0.038(5) 0.059(7) 0.043(7) -0.001(6) 0.015(4) 0.007(4) C5 0.035(5) 0.039(6) 0.034(6) -0.006(5) 0.005(4) 0.004(4) C6 0.024(4) 0.052(6) 0.024(6) 0.011(4) 0.008(4) 0.005(4) C7 0.040(5) 0.055(6) 0.018(5) -0.001(4) -0.001(4) 0.007(4) C8 0.043(5) 0.052(7) 0.032(6) 0.015(5) 0.013(4) 0.009(4) C9 0.039(5) 0.029(6) 0.038(6) 0.002(4) 0.012(4) 0.005(4) C10 0.029(4) 0.031(5) 0.039(6) -0.006(4) 0.004(4) -0.004(4) C11 0.026(4) 0.030(5) 0.041(7) -0.005(4) 0.007(4) 0.000(4) C12 0.046(5) 0.027(5) 0.048(7) -0.002(4) 0.019(5) -0.002(4) C13 0.050(5) 0.029(5) 0.052(6) -0.002(4) -0.008(4) 0.003(4) C14 0.052(6) 0.048(6) 0.037(6) -0.013(5) 0.002(4) -0.010(4) C15 0.061(6) 0.043(6) 0.046(7) -0.006(5) 0.010(5) -0.002(5) C16 0.029(5) 0.036(5) 0.040(7) -0.007(5) 0.010(4) 0.005(4) C17 0.014(4) 0.039(5) 0.031(6) -0.011(4) 0.008(4) 0.001(3) C18 0.032(5) 0.039(5) 0.039(6) -0.003(5) 0.004(4) -0.001(4) C19 0.035(5) 0.063(8) 0.022(5) -0.005(4) -0.007(4) 0.001(4) C20 0.034(5) 0.058(7) 0.052(8) 0.010(6) 0.014(4) 0.007(4) C21 0.045(5) 0.055(7) 0.042(7) 0.019(5) 0.003(5) 0.009(5) C22 0.037(5) 0.050(6) 0.036(7) -0.008(5) -0.004(4) -0.004(4) C23 0.057(6) 0.047(5) 0.028(6) 0.005(5) 0.007(5) 0.007(5) C24 0.049(5) 0.081(7) 0.054(7) -0.001(6) 0.019(5) 0.015(5) Cl1 0.0488(13) 0.0319(12) 0.0534(17) -0.0004(11) 0.0108(11) -0.0079(10) O11 0.051(4) 0.045(4) 0.130(7) -0.011(4) 0.054(4) -0.019(3) O12 0.120(7) 0.083(6) 0.171(12) 0.083(7) -0.031(7) -0.040(5) O13 0.136(7) 0.114(7) 0.046(6) -0.031(5) 0.031(5) -0.020(6) O14 0.060(5) 0.160(8) 0.141(8) -0.086(7) 0.070(5) -0.060(5) Cl2 0.0479(13) 0.0461(14) 0.0343(15) 0.0041(11) 0.0066(11) 0.0130(10) O21 0.130(5) 0.171(6) 0.116(5) -0.060(4) 0.019(4) 0.003(4) O22 0.130(5) 0.171(6) 0.116(5) -0.060(4) 0.019(4) 0.003(4) O23 0.130(5) 0.171(6) 0.116(5) -0.060(4) 0.019(4) 0.003(4) O24 0.130(5) 0.171(6) 0.116(5) -0.060(4) 0.019(4) 0.003(4) #=============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; 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 O1W 2.145(6) . . yes Co1 N1 2.154(7) . . yes Co1 N2 2.112(8) . . yes Co1 N3 2.107(7) . . yes Co1 N4 2.160(7) . . yes Co1 N5 2.086(7) . . yes Cl1 O11 1.430(7) . . yes Cl1 O12 1.369(10) . . yes Cl1 O13 1.428(8) . . yes Cl1 O14 1.376(8) . . yes Cl2 O21 1.369(13) . . yes Cl2 O22 1.375(12) . . yes Cl2 O23 1.376(11) . . yes Cl2 O24 1.388(12) . . yes O1W H1WB 0.85(7) . . no O1W H1WA 0.85(7) . . no N1 C5 1.394(12) . . yes N1 C1 1.300(12) . . yes N2 C6 1.332(12) . . yes N2 C10 1.356(11) . . yes N3 C11 1.355(11) . . yes N3 C17 1.327(11) . . yes N4 C22 1.350(12) . . yes N4 C18 1.351(12) . . yes N5 C23 1.151(12) . . yes N6 C13 1.309(11) . . yes N6 C12 1.391(11) . . yes N7 C17 1.331(12) . . yes N7 C16 1.397(13) . . yes C1 C2 1.359(14) . . no C2 C3 1.350(14) . . no C3 C4 1.357(14) . . no C4 C5 1.420(14) . . no C5 C6 1.474(12) . . no C6 C7 1.377(13) . . no C7 C8 1.397(14) . . no C8 C9 1.328(14) . . no C9 C10 1.413(13) . . no C10 C11 1.492(12) . . no C11 C12 1.437(12) . . no C12 C16 1.365(14) . . no C13 C14 1.381(14) . . no C14 C15 1.380(13) . . no C15 C16 1.415(13) . . no C17 C18 1.485(12) . . no C18 C19 1.387(13) . . no C19 C20 1.376(15) . . no C20 C21 1.413(15) . . no C21 C22 1.351(15) . . no C23 C24 1.424(14) . . no C1 H1A 0.9500 . . no C2 H2A 0.9500 . . no C3 H3A 0.9500 . . no C4 H4A 0.9500 . . no C7 H7A 0.9500 . . no C8 H8A 0.9500 . . no C9 H9A 0.9500 . . no C13 H13A 0.9500 . . no C14 H14A 0.9500 . . no C15 H15A 0.9500 . . no C19 H19A 0.9500 . . no C20 H20A 0.9500 . . no C21 H21A 0.9500 . . no C22 H22A 0.9500 . . no C24 H24B 0.9800 . . no C24 H24C 0.9800 . . no C24 H24A 0.9800 . . no 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 O1W Co1 N1 88.5(3) . . . yes O1W Co1 N2 92.4(3) . . . yes O1W Co1 N3 91.9(2) . . . yes O1W Co1 N4 85.9(3) . . . yes O1W Co1 N5 173.7(3) . . . yes N1 Co1 N2 76.5(3) . . . yes N1 Co1 N3 150.6(3) . . . yes N1 Co1 N4 133.4(3) . . . yes N1 Co1 N5 90.2(3) . . . yes N2 Co1 N3 74.2(3) . . . yes N2 Co1 N4 150.0(3) . . . yes N2 Co1 N5 93.3(3) . . . yes N3 Co1 N4 75.9(3) . . . yes N3 Co1 N5 92.2(3) . . . yes N4 Co1 N5 90.5(3) . . . yes O12 Cl1 O13 105.6(6) . . . yes O12 Cl1 O14 110.3(6) . . . yes O13 Cl1 O14 110.5(6) . . . yes O11 Cl1 O12 108.7(5) . . . yes O11 Cl1 O13 109.4(5) . . . yes O11 Cl1 O14 112.2(5) . . . yes O21 Cl2 O22 117.2(7) . . . yes O21 Cl2 O23 111.9(7) . . . yes O21 Cl2 O24 100.1(7) . . . yes O23 Cl2 O24 116.4(7) . . . yes O22 Cl2 O23 106.2(7) . . . yes O22 Cl2 O24 105.3(7) . . . yes Co1 O1W H1WB 118(5) . . . no H1WA O1W H1WB 96(7) . . . no Co1 O1W H1WA 140(5) . . . no C1 N1 C5 119.1(8) . . . yes Co1 N1 C5 114.3(5) . . . yes Co1 N1 C1 126.6(6) . . . yes Co1 N2 C6 118.6(6) . . . yes C6 N2 C10 121.4(8) . . . yes Co1 N2 C10 120.0(6) . . . yes Co1 N3 C11 120.1(6) . . . yes C11 N3 C17 121.6(7) . . . yes Co1 N3 C17 118.3(5) . . . yes C18 N4 C22 118.6(8) . . . yes Co1 N4 C22 126.1(6) . . . yes Co1 N4 C18 115.3(6) . . . yes Co1 N5 C23 173.9(7) . . . yes C12 N6 C13 113.1(8) . . . yes C16 N7 C17 112.9(8) . . . yes N1 C1 C2 123.4(9) . . . yes C1 C2 C3 118.7(10) . . . no C2 C3 C4 122.0(9) . . . no C3 C4 C5 117.4(9) . . . no N1 C5 C4 119.3(8) . . . yes C4 C5 C6 125.1(8) . . . no N1 C5 C6 115.6(8) . . . yes N2 C6 C5 115.0(8) . . . yes N2 C6 C7 122.1(8) . . . yes C5 C6 C7 122.9(8) . . . no C6 C7 C8 116.4(8) . . . no C7 C8 C9 122.2(9) . . . no C8 C9 C10 119.7(9) . . . no N2 C10 C9 118.1(8) . . . yes N2 C10 C11 112.7(7) . . . yes C9 C10 C11 129.2(8) . . . no C10 C11 C12 129.9(8) . . . no N3 C11 C12 117.1(8) . . . yes N3 C11 C10 113.0(7) . . . yes N6 C12 C11 116.7(8) . . . yes N6 C12 C16 126.6(8) . . . yes C11 C12 C16 116.7(8) . . . no N6 C13 C14 126.1(8) . . . yes C13 C14 C15 119.5(9) . . . no C14 C15 C16 117.8(9) . . . no N7 C16 C15 117.8(9) . . . yes N7 C16 C12 125.3(9) . . . yes C12 C16 C15 116.8(8) . . . no N3 C17 C18 115.0(7) . . . yes N3 C17 N7 126.2(8) . . . yes N7 C17 C18 118.8(8) . . . yes N4 C18 C17 115.5(8) . . . yes C17 C18 C19 122.9(9) . . . no N4 C18 C19 121.6(9) . . . yes C18 C19 C20 119.7(9) . . . no C19 C20 C21 117.7(10) . . . no C20 C21 C22 119.9(10) . . . no N4 C22 C21 122.3(9) . . . yes N5 C23 C24 178.3(10) . . . yes C2 C1 H1A 118.00 . . . no N1 C1 H1A 118.00 . . . no C1 C2 H2A 121.00 . . . no C3 C2 H2A 121.00 . . . no C4 C3 H3A 119.00 . . . no C2 C3 H3A 119.00 . . . no C3 C4 H4A 121.00 . . . no C5 C4 H4A 121.00 . . . no C6 C7 H7A 122.00 . . . no C8 C7 H7A 122.00 . . . no C7 C8 H8A 119.00 . . . no C9 C8 H8A 119.00 . . . no C10 C9 H9A 120.00 . . . no C8 C9 H9A 120.00 . . . no N6 C13 H13A 117.00 . . . no C14 C13 H13A 117.00 . . . no C15 C14 H14A 120.00 . . . no C13 C14 H14A 120.00 . . . no C14 C15 H15A 121.00 . . . no C16 C15 H15A 121.00 . . . no C18 C19 H19A 120.00 . . . no C20 C19 H19A 120.00 . . . no C21 C20 H20A 121.00 . . . no C19 C20 H20A 121.00 . . . no C20 C21 H21A 120.00 . . . no C22 C21 H21A 120.00 . . . no N4 C22 H22A 119.00 . . . no C21 C22 H22A 119.00 . . . no H24B C24 H24C 109.00 . . . no H24A C24 H24B 109.00 . . . no H24A C24 H24C 109.00 . . . no C23 C24 H24A 109.00 . . . no C23 C24 H24B 109.00 . . . no C23 C24 H24C 110.00 . . . 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1W Co1 N1 C1 -87.4(8) . . . . no O1W Co1 N1 C5 90.8(6) . . . . no N2 Co1 N1 C1 179.7(8) . . . . no N2 Co1 N1 C5 -2.0(6) . . . . no N3 Co1 N1 C1 -178.7(6) . . . . no N3 Co1 N1 C5 -0.4(9) . . . . no N4 Co1 N1 C1 -4.5(9) . . . . no N4 Co1 N1 C5 173.8(5) . . . . no N5 Co1 N1 C1 86.4(8) . . . . no N5 Co1 N1 C5 -95.3(6) . . . . no O1W Co1 N2 C6 -86.1(6) . . . . no O1W Co1 N2 C10 93.4(6) . . . . no N1 Co1 N2 C6 1.8(6) . . . . no N1 Co1 N2 C10 -178.7(7) . . . . no N3 Co1 N2 C6 -177.4(7) . . . . no N3 Co1 N2 C10 2.1(6) . . . . no N4 Co1 N2 C6 -172.0(6) . . . . no N4 Co1 N2 C10 7.4(10) . . . . no N5 Co1 N2 C6 91.2(6) . . . . no N5 Co1 N2 C10 -89.3(6) . . . . no O1W Co1 N3 C11 -94.6(6) . . . . no O1W Co1 N3 C17 87.3(6) . . . . no N1 Co1 N3 C11 -4.3(9) . . . . no N1 Co1 N3 C17 177.7(6) . . . . no N2 Co1 N3 C11 -2.7(6) . . . . no N2 Co1 N3 C17 179.3(6) . . . . no N4 Co1 N3 C11 -179.9(6) . . . . no N4 Co1 N3 C17 2.0(5) . . . . no N5 Co1 N3 C11 90.1(6) . . . . no N5 Co1 N3 C17 -88.0(6) . . . . no O1W Co1 N4 C18 -94.4(6) . . . . no O1W Co1 N4 C22 87.0(7) . . . . no N1 Co1 N4 C18 -178.5(6) . . . . no N1 Co1 N4 C22 3.0(9) . . . . no N2 Co1 N4 C18 -6.7(10) . . . . no N2 Co1 N4 C22 174.7(7) . . . . no N3 Co1 N4 C18 -1.4(6) . . . . no N3 Co1 N4 C22 -180.0(8) . . . . no N5 Co1 N4 C18 90.8(6) . . . . no N5 Co1 N4 C22 -87.8(7) . . . . no Co1 N1 C1 C2 179.6(7) . . . . no C5 N1 C1 C2 1.4(13) . . . . no Co1 N1 C5 C4 -178.4(6) . . . . no Co1 N1 C5 C6 2.0(9) . . . . no C1 N1 C5 C4 0.0(13) . . . . no C1 N1 C5 C6 -179.6(8) . . . . no Co1 N2 C6 C5 -1.3(9) . . . . no Co1 N2 C6 C7 177.7(6) . . . . no C10 N2 C6 C5 179.2(7) . . . . no C10 N2 C6 C7 -1.7(12) . . . . no Co1 N2 C10 C9 179.3(6) . . . . no Co1 N2 C10 C11 -1.3(9) . . . . no C6 N2 C10 C9 -1.3(12) . . . . no C6 N2 C10 C11 178.2(7) . . . . no Co1 N3 C11 C10 2.9(9) . . . . no Co1 N3 C11 C12 -176.6(6) . . . . no C17 N3 C11 C10 -179.2(7) . . . . no C17 N3 C11 C12 1.4(12) . . . . no Co1 N3 C17 N7 179.8(6) . . . . no Co1 N3 C17 C18 -2.3(9) . . . . no C11 N3 C17 N7 1.8(12) . . . . no C11 N3 C17 C18 179.7(7) . . . . no Co1 N4 C18 C17 0.7(10) . . . . no Co1 N4 C18 C19 -179.8(6) . . . . no C22 N4 C18 C17 179.4(7) . . . . no C22 N4 C18 C19 -1.1(13) . . . . no Co1 N4 C22 C21 -177.9(7) . . . . no C18 N4 C22 C21 3.5(13) . . . . no C13 N6 C12 C11 179.2(8) . . . . no C13 N6 C12 C16 -1.4(13) . . . . no C12 N6 C13 C14 2.0(13) . . . . no C17 N7 C16 C12 5.3(13) . . . . no C17 N7 C16 C15 -178.3(8) . . . . no C16 N7 C17 N3 -4.9(12) . . . . no C16 N7 C17 C18 177.3(7) . . . . no N1 C1 C2 C3 -1.1(14) . . . . no C1 C2 C3 C4 -0.7(14) . . . . no C2 C3 C4 C5 1.9(14) . . . . no C3 C4 C5 N1 -1.5(13) . . . . no C3 C4 C5 C6 178.0(8) . . . . no N1 C5 C6 N2 -0.5(11) . . . . no N1 C5 C6 C7 -179.5(8) . . . . no C4 C5 C6 N2 180.0(8) . . . . no C4 C5 C6 C7 0.9(13) . . . . no N2 C6 C7 C8 1.6(12) . . . . no C5 C6 C7 C8 -179.4(8) . . . . no C6 C7 C8 C9 1.6(13) . . . . no C7 C8 C9 C10 -4.5(14) . . . . no C8 C9 C10 N2 4.4(12) . . . . no C8 C9 C10 C11 -175.0(9) . . . . no N2 C10 C11 N3 -1.0(10) . . . . no N2 C10 C11 C12 178.4(9) . . . . no C9 C10 C11 N3 178.4(8) . . . . no C9 C10 C11 C12 -2.3(15) . . . . no N3 C11 C12 N6 178.6(7) . . . . no N3 C11 C12 C16 -0.9(12) . . . . no C10 C11 C12 N6 -0.7(14) . . . . no C10 C11 C12 C16 179.8(8) . . . . no N6 C12 C16 N7 177.9(8) . . . . no N6 C12 C16 C15 1.5(14) . . . . no C11 C12 C16 N7 -2.7(14) . . . . no C11 C12 C16 C15 -179.0(8) . . . . no N6 C13 C14 C15 -2.8(15) . . . . no C13 C14 C15 C16 2.7(13) . . . . no C14 C15 C16 N7 -178.7(8) . . . . no C14 C15 C16 C12 -2.1(13) . . . . no N3 C17 C18 N4 1.0(11) . . . . no N3 C17 C18 C19 -178.5(8) . . . . no N7 C17 C18 N4 179.1(7) . . . . no N7 C17 C18 C19 -0.5(12) . . . . no N4 C18 C19 C20 -1.5(13) . . . . no C17 C18 C19 C20 178.0(8) . . . . no C18 C19 C20 C21 1.7(12) . . . . no C19 C20 C21 C22 0.6(13) . . . . no C20 C21 C22 N4 -3.3(14) . . . . 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 Cl1 H1WA 2.97(7) . 3_555 no Cl2 H1WB 2.80(7) . 3_545 no O1W N3 3.057(9) . . no O1W N1 3.000(9) . . no O1W N2 3.073(10) . . no O1W C8 3.308(11) . 2_565 no O1W N4 2.933(9) . . no O1W O24 2.813(13) . 3_455 no O1W O12 2.721(12) . 3_445 no O11 C18 3.417(11) . . no O11 C23 3.068(12) . . no O11 N5 3.195(10) . . no O11 N3 3.180(9) . . no O11 C17 2.927(10) . . no O11 N7 3.173(10) . . no O11 C3 3.287(12) . 4_555 no O12 O1W 2.721(12) . 3_555 no O14 C22 3.362(13) . 3_555 no O21 C1 3.280(15) . . no O21 C15 2.998(16) . 2_564 no O21 C14 3.132(16) . 2_564 no O22 C11 3.150(15) . 3_545 no O22 C10 3.042(14) . 3_545 no O22 C4 3.272(15) . 4_555 no O23 C22 3.272(14) . . no O23 C13 3.381(14) . 1_545 no O24 C21 3.400(16) . 2_554 no O24 O1W 2.813(13) . 3_545 no O1W H8A 2.7400 . 2_565 no O11 H24C 2.9200 . . no O11 H3A 2.5300 . 4_555 no O12 H1WA 1.92(7) . 3_555 no O12 H20A 2.5600 . 2_564 no O13 H8A 2.7600 . 4_565 no O13 H24A 2.5700 . 2_565 no O13 H2A 2.8500 . 4_555 no O14 H24C 2.6600 . . no O14 H22A 2.6300 . 3_555 no O14 H1A 2.7500 . 3_555 no O21 H15A 2.3500 . 2_564 no O21 H14A 2.6300 . 2_564 no O22 H7A 2.7000 . 4_555 no O22 H1WB 2.63(7) . 3_545 no O22 H4A 2.3600 . 4_555 no O23 H13A 2.6700 . 1_545 no O23 H22A 2.5100 . . no O23 H1A 2.9100 . . no O24 H1WB 2.00(8) . 3_545 no O24 H21A 2.6100 . 2_554 no N1 O1W 3.000(9) . . no N1 N5 3.004(10) . . no N1 C6 2.428(11) . . no N1 N2 2.640(10) . . no N2 O1W 3.073(10) . . no N2 N1 2.640(10) . . no N2 N5 3.053(10) . . no N2 C5 2.368(12) . . no N2 N3 2.544(11) . . no N2 C11 2.372(11) . . no N3 C18 2.373(12) . . no N3 O1W 3.057(9) . . no N3 O11 3.180(9) . . no N3 N2 2.544(11) . . no N3 N4 2.626(10) . . no N3 N5 3.022(10) . . no N3 C10 2.374(11) . . no N4 C17 2.399(10) . . no N4 N3 2.626(10) . . no N4 O1W 2.933(9) . . no N4 N5 3.017(10) . . no N5 N2 3.053(10) . . no N5 N1 3.004(10) . . no N5 O11 3.195(10) . . no N5 N3 3.022(10) . . no N5 N4 3.017(10) . . no N6 C9 3.041(12) . . no N7 O11 3.173(10) . . no N7 C23 3.410(12) . 2_565 no N6 H24B 2.6800 . 3_455 no N6 H9A 2.4600 . . no N7 H19A 2.5900 . . no N7 H24A 2.9400 . 2_565 no C1 O21 3.280(15) . . no C3 O11 3.287(12) . 4_454 no C4 C21 3.546(13) . 4_454 no C4 O22 3.272(15) . 4_454 no C7 C17 3.578(12) . 2_564 no C8 O1W 3.308(11) . 2_564 no C8 C18 3.508(13) . 2_564 no C9 C19 3.367(12) . 2_564 no C9 N6 3.041(12) . . no C9 C20 3.432(13) . 2_564 no C10 O22 3.042(14) . 3_455 no C10 C19 3.513(11) . 2_564 no C11 O22 3.150(15) . 3_455 no C13 O23 3.381(14) . 1_565 no C14 O21 3.132(16) . 2_565 no C15 O21 2.998(16) . 2_565 no C17 C7 3.578(12) . 2_565 no C17 O11 2.927(10) . . no C18 O11 3.417(11) . . no C18 C8 3.508(13) . 2_565 no C19 C10 3.513(11) . 2_565 no C19 C9 3.367(12) . 2_565 no C20 C9 3.432(13) . 2_565 no C21 C4 3.546(13) . 4_555 no C21 O24 3.400(16) . 2_555 no C22 O14 3.362(13) . 3_445 no C22 O23 3.272(14) . . no C23 N7 3.410(12) . 2_564 no C23 O11 3.068(12) . . no C4 H7A 2.7700 . . no C7 H4A 2.8000 . . no C9 H24B 3.0800 . 3_455 no C23 H19A 3.0500 . 2_564 no C23 H15A 2.8600 . 2_564 no H1WA Cl1 2.97(7) . 3_445 no H1WA O12 1.92(7) . 3_445 no H1WA H8A 2.4600 . 2_565 no H1A O23 2.9100 . . no H1A O14 2.7500 . 3_445 no H1WB Cl2 2.80(7) . 3_455 no H1WB O22 2.63(7) . 3_455 no H1WB O24 2.00(8) . 3_455 no H2A O13 2.8500 . 4_454 no H3A O11 2.5300 . 4_454 no H4A C7 2.8000 . . no H4A H7A 2.2500 . . no H4A O22 2.3600 . 4_454 no H7A O22 2.7000 . 4_454 no H7A H4A 2.2500 . . no H7A C4 2.7700 . . no H8A O13 2.7600 . 4_464 no H8A O1W 2.7400 . 2_564 no H8A H1WA 2.4600 . 2_564 no H9A N6 2.4600 . . no H9A H24B 2.4600 . 3_455 no H13A O23 2.6700 . 1_565 no H14A O21 2.6300 . 2_565 no H15A C23 2.8600 . 2_565 no H15A O21 2.3500 . 2_565 no H19A C23 3.0500 . 2_565 no H19A N7 2.5900 . . no H20A O12 2.5600 . 2_565 no H21A O24 2.6100 . 2_555 no H22A O23 2.5100 . . no H22A O14 2.6300 . 3_445 no H24A N7 2.9400 . 2_564 no H24A O13 2.5700 . 2_564 no H24B C9 3.0800 . 3_545 no H24B N6 2.6800 . 3_545 no H24B H9A 2.4600 . 3_545 no H24C O11 2.9200 . . no H24C O14 2.6600 . . no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # O1W H1WA O12 0.85(7) 1.92(7) 2.721(12) 156(8) 3_445 yes O1W H1WB O24 0.85(7) 2.00(8) 2.813(13) 158(8) 3_455 yes C3 H3A O11 0.9500 2.5300 3.287(12) 137.00 4_454 yes C4 H4A O22 0.9500 2.3600 3.272(15) 160.00 4_454 yes C9 H9A N6 0.9500 2.4600 3.041(12) 120.00 . yes C15 H15A O21 0.9500 2.3500 2.998(16) 125.00 2_565 yes C20 H20A O12 0.9500 2.5600 3.444(16) 154.00 2_565 yes C22 H22A O23 0.9500 2.5100 3.272(14) 137.00 . yes C24 H24A O13 0.9800 2.5700 3.445(12) 148.00 2_564 yes _diffrn_measured_fraction_theta_max 0.966 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.681 _refine_diff_density_min -0.571 _refine_diff_density_rms 0.089