# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Vincent L Pecoraro' _publ_contact_author_email VLPEC@UMICH.EDU _publ_section_title ; Corroborative Cobalt and Zinc model compounds of alpha-amino-beta-carboxymuconic-epsilon-semialdehyde decarboxylase (ACMSD) ; loop_ _publ_author_name 'Vincent L Pecoraro' 'Jessica Gatjens' 'Jeff W Kampf' 'Christopher S Mullins' 'Pierre Thuery' # Attachment 'CIF_Manuscript_VLPecoraro.txt' # # Title: Corroborative Cobalt and Zinc model compounds # of alpha-amino-beta-carboxymuconic-epsilon- # semialdehyde decarboxylase (ACMSD) # # Authors: J. G\"atjens, C. S. Mullins, J.W. Kampf, P. Thu\'ery, # and V.L. Pecoraro # data_1 _database_code_depnum_ccdc_archive 'CCDC 690379' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H22 Cl Co N5 O2' _chemical_formula_sum 'C15 H22 Cl Co N5 O2' _chemical_formula_weight 398.76 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' O O 0.0106 0.0060 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 13.303(2) _cell_length_b 10.8182(16) _cell_length_c 12.6257(19) _cell_angle_alpha 90.00 _cell_angle_beta 104.526(10) _cell_angle_gamma 90.00 _cell_volume 1758.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 6303 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 24.41 _exptl_crystal_description plate _exptl_crystal_colour blue _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.506 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 828 _exptl_absorpt_coefficient_mu 1.146 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6832 _exptl_absorpt_correction_T_max 0.9039 _exptl_absorpt_process_details ; Blessing, R. Acta Cryst. (1995) A51 33-38. Sheldrick, G. SADABS (Version 2.10) Bruker/Siemens area detector absorption and other corrections, University of Gottingen, Germany 2003. ; _exptl_special_details ; 2645 frames x 30 sec. @ 4.969 cm; 0.5 deg. steps in omega & phi ; _diffrn_ambient_temperature 123(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30883 _diffrn_reflns_av_R_equivalents 0.0681 _diffrn_reflns_av_sigmaI/netI 0.0398 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.46 _diffrn_reflns_theta_max 26.71 _reflns_number_total 3633 _reflns_number_gt 2593 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0318P)^2^+1.6268P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3633 _refine_ls_number_parameters 222 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0636 _refine_ls_R_factor_gt 0.0347 _refine_ls_wR_factor_ref 0.0855 _refine_ls_wR_factor_gt 0.0767 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.009 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.31806(7) 0.55660(7) 0.83921(6) 0.0468(2) Uani 1 1 d . . . Co1 Co 0.27998(3) 0.45656(3) 0.67426(3) 0.02685(11) Uani 1 1 d . . . O1 O 0.22133(14) 0.30827(16) 0.72902(13) 0.0283(4) Uani 1 1 d . . . O2 O 0.15905(17) 0.11748(18) 0.70382(15) 0.0416(5) Uani 1 1 d . . . C1 C 0.1955(2) 0.2103(2) 0.6723(2) 0.0269(6) Uani 1 1 d . . . C2 C 0.2211(2) 0.2072(2) 0.5594(2) 0.0283(6) Uani 1 1 d . . . H2A H 0.2927 0.1722 0.5723 0.034 Uiso 1 1 calc R . . C3 C 0.1505(2) 0.1210(3) 0.4778(2) 0.0389(7) Uani 1 1 d . . . H3A H 0.0780 0.1463 0.4681 0.058 Uiso 1 1 calc R . . H3B H 0.1594 0.0361 0.5055 0.058 Uiso 1 1 calc R . . H3C H 0.1688 0.1253 0.4073 0.058 Uiso 1 1 calc R . . C4 C 0.1262(2) 0.3852(2) 0.4603(2) 0.0299(6) Uani 1 1 d . . . H4A H 0.1103 0.3591 0.3827 0.036 Uiso 1 1 calc R . . H4B H 0.0708 0.3536 0.4929 0.036 Uiso 1 1 calc R . . C5 C 0.0817(2) 0.6073(3) 0.3961(2) 0.0356(7) Uani 1 1 d . . . C6 C 0.1044(2) 0.7187(3) 0.4483(3) 0.0427(8) Uani 1 1 d . . . H6A H 0.0815 0.7976 0.4189 0.051 Uiso 1 1 calc R . . C7 C 0.1671(2) 0.6953(3) 0.5525(3) 0.0389(7) Uani 1 1 d . . . C8 C 0.30610(19) 0.3495(2) 0.45773(19) 0.0274(6) Uani 1 1 d . . . H8A H 0.2931 0.4252 0.4124 0.033 Uiso 1 1 calc R . . H8B H 0.3042 0.2774 0.4089 0.033 Uiso 1 1 calc R . . C9 C 0.5011(2) 0.3174(2) 0.5280(2) 0.0303(6) Uani 1 1 d . . . C10 C 0.5728(2) 0.3705(2) 0.6136(2) 0.0332(6) Uani 1 1 d . . . H10A H 0.6461 0.3607 0.6295 0.040 Uiso 1 1 calc R . . C11 C 0.5184(2) 0.4414(2) 0.6726(2) 0.0299(6) Uani 1 1 d . . . C12 C 0.0145(3) 0.5757(3) 0.2860(2) 0.0481(9) Uani 1 1 d . . . H12A H 0.0555 0.5310 0.2439 0.072 Uiso 1 1 calc R . . H12B H -0.0131 0.6518 0.2474 0.072 Uiso 1 1 calc R . . H12C H -0.0432 0.5234 0.2946 0.072 Uiso 1 1 calc R . . C13 C 0.2134(3) 0.7840(3) 0.6421(3) 0.0603(10) Uani 1 1 d . . . H13A H 0.1952 0.7588 0.7094 0.090 Uiso 1 1 calc R . . H13B H 0.1863 0.8672 0.6213 0.090 Uiso 1 1 calc R . . H13C H 0.2891 0.7843 0.6542 0.090 Uiso 1 1 calc R . . C14 C 0.5148(2) 0.2305(3) 0.4405(2) 0.0383(7) Uani 1 1 d . . . H14A H 0.4579 0.1704 0.4251 0.058 Uiso 1 1 calc R . . H14B H 0.5812 0.1870 0.4653 0.058 Uiso 1 1 calc R . . H14C H 0.5144 0.2773 0.3739 0.058 Uiso 1 1 calc R . . C15 C 0.5605(2) 0.5198(3) 0.7715(2) 0.0366(7) Uani 1 1 d . . . H15A H 0.5028 0.5565 0.7960 0.055 Uiso 1 1 calc R . . H15B H 0.6038 0.5857 0.7531 0.055 Uiso 1 1 calc R . . H15C H 0.6025 0.4687 0.8302 0.055 Uiso 1 1 calc R . . N1 N 0.22748(16) 0.33619(18) 0.51992(16) 0.0227(4) Uani 1 1 d . . . N2 N 0.13136(17) 0.5205(2) 0.46792(17) 0.0296(5) Uani 1 1 d . . . N3 N 0.18346(18) 0.5724(2) 0.56524(19) 0.0330(5) Uani 1 1 d . . . N4 N 0.40727(16) 0.3572(2) 0.53710(17) 0.0281(5) Uani 1 1 d . . . N5 N 0.41562(17) 0.43378(19) 0.62572(17) 0.0286(5) Uani 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 0.0615(5) 0.0425(4) 0.0341(4) -0.0169(3) 0.0074(4) -0.0095(4) Co1 0.0306(2) 0.02643(18) 0.02151(18) -0.00220(15) 0.00287(14) -0.00192(16) O1 0.0360(11) 0.0306(10) 0.0180(9) -0.0012(7) 0.0059(8) -0.0026(8) O2 0.0635(14) 0.0375(11) 0.0267(10) 0.0005(9) 0.0168(10) -0.0162(10) C1 0.0283(14) 0.0314(14) 0.0191(13) 0.0039(11) 0.0025(11) 0.0021(11) C2 0.0390(16) 0.0261(13) 0.0184(13) 0.0026(10) 0.0046(11) -0.0027(11) C3 0.062(2) 0.0338(15) 0.0206(14) -0.0039(12) 0.0097(14) -0.0132(14) C4 0.0311(15) 0.0356(15) 0.0204(13) 0.0023(11) 0.0018(11) -0.0018(12) C5 0.0313(16) 0.0470(17) 0.0321(15) 0.0147(13) 0.0148(12) 0.0134(13) C6 0.0372(17) 0.0344(16) 0.060(2) 0.0153(15) 0.0179(15) 0.0087(13) C7 0.0299(16) 0.0298(15) 0.057(2) 0.0057(13) 0.0110(14) 0.0037(12) C8 0.0302(15) 0.0319(14) 0.0189(13) 0.0017(11) 0.0035(11) -0.0035(11) C9 0.0305(15) 0.0289(13) 0.0309(15) 0.0095(12) 0.0068(12) 0.0024(12) C10 0.0271(15) 0.0349(15) 0.0345(15) 0.0115(12) 0.0019(12) -0.0009(12) C11 0.0299(15) 0.0270(13) 0.0290(14) 0.0070(11) 0.0005(11) -0.0044(11) C12 0.049(2) 0.067(2) 0.0287(16) 0.0143(15) 0.0115(14) 0.0273(17) C13 0.047(2) 0.0293(16) 0.097(3) -0.0141(18) 0.004(2) -0.0013(15) C14 0.0407(17) 0.0425(17) 0.0320(16) 0.0046(13) 0.0095(13) 0.0078(14) C15 0.0339(16) 0.0370(16) 0.0329(15) 0.0023(12) -0.0029(12) -0.0089(12) N1 0.0260(11) 0.0250(10) 0.0163(10) 0.0025(8) 0.0040(9) -0.0018(9) N2 0.0329(13) 0.0315(12) 0.0239(12) 0.0057(9) 0.0060(10) 0.0032(10) N3 0.0346(13) 0.0283(12) 0.0338(13) 0.0008(10) 0.0041(11) -0.0014(10) N4 0.0271(12) 0.0327(12) 0.0225(11) -0.0017(9) 0.0026(9) -0.0031(10) N5 0.0321(13) 0.0302(12) 0.0218(11) -0.0018(9) 0.0031(9) -0.0046(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 Co1 2.2881(8) . ? Co1 O1 1.9826(18) . ? Co1 N3 2.056(2) . ? Co1 N5 2.061(2) . ? Co1 N1 2.302(2) . ? O1 C1 1.277(3) . ? O2 C1 1.224(3) . ? C1 C2 1.547(3) . ? C2 N1 1.491(3) . ? C2 C3 1.526(4) . ? C4 N2 1.467(3) . ? C4 N1 1.468(3) . ? C5 N2 1.357(3) . ? C5 C6 1.371(4) . ? C5 C12 1.491(4) . ? C6 C7 1.393(4) . ? C7 N3 1.350(3) . ? C7 C13 1.493(4) . ? C8 N1 1.464(3) . ? C8 N4 1.465(3) . ? C9 N4 1.352(3) . ? C9 C10 1.375(4) . ? C9 C14 1.496(4) . ? C10 C11 1.391(4) . ? C11 N5 1.350(3) . ? C11 C15 1.498(4) . ? N2 N3 1.371(3) . ? N4 N5 1.374(3) . ? 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 O1 Co1 N3 119.50(8) . . ? O1 Co1 N5 117.22(8) . . ? N3 Co1 N5 108.67(9) . . ? O1 Co1 Cl1 94.70(5) . . ? N3 Co1 Cl1 106.23(7) . . ? N5 Co1 Cl1 108.46(6) . . ? O1 Co1 N1 77.00(7) . . ? N3 Co1 N1 76.83(8) . . ? N5 Co1 N1 77.47(8) . . ? Cl1 Co1 N1 171.50(6) . . ? C1 O1 Co1 123.37(16) . . ? O2 C1 O1 124.8(2) . . ? O2 C1 C2 118.6(2) . . ? O1 C1 C2 116.4(2) . . ? N1 C2 C3 115.0(2) . . ? N1 C2 C1 109.4(2) . . ? C3 C2 C1 113.3(2) . . ? N2 C4 N1 107.7(2) . . ? N2 C5 C6 106.0(3) . . ? N2 C5 C12 122.8(3) . . ? C6 C5 C12 131.2(3) . . ? C5 C6 C7 107.6(3) . . ? N3 C7 C6 109.4(3) . . ? N3 C7 C13 121.3(3) . . ? C6 C7 C13 129.3(3) . . ? N1 C8 N4 107.23(19) . . ? N4 C9 C10 105.9(2) . . ? N4 C9 C14 123.3(2) . . ? C10 C9 C14 130.8(3) . . ? C9 C10 C11 107.4(2) . . ? N5 C11 C10 109.7(2) . . ? N5 C11 C15 121.7(2) . . ? C10 C11 C15 128.5(3) . . ? C8 N1 C4 112.14(19) . . ? C8 N1 C2 112.3(2) . . ? C4 N1 C2 112.8(2) . . ? C8 N1 Co1 107.02(14) . . ? C4 N1 Co1 105.94(15) . . ? C2 N1 Co1 106.08(14) . . ? C5 N2 N3 111.6(2) . . ? C5 N2 C4 129.8(2) . . ? N3 N2 C4 118.2(2) . . ? C7 N3 N2 105.5(2) . . ? C7 N3 Co1 137.3(2) . . ? N2 N3 Co1 116.15(16) . . ? C9 N4 N5 111.9(2) . . ? C9 N4 C8 129.3(2) . . ? N5 N4 C8 117.6(2) . . ? C11 N5 N4 105.1(2) . . ? C11 N5 Co1 136.79(18) . . ? N4 N5 Co1 114.59(16) . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 26.71 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.292 _refine_diff_density_min -0.325 _refine_diff_density_rms 0.064 #===END data_2 _database_code_depnum_ccdc_archive 'CCDC 690380' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H36 Cl Co N5 O2, C H4 O' _chemical_formula_sum 'C23 H40 Cl Co N5 O3' _chemical_formula_weight 528.98 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.2282(12) _cell_length_b 13.5079(11) _cell_length_c 15.4267(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.426(6) _cell_angle_gamma 90.00 _cell_volume 2756.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 6652 _cell_measurement_theta_min 2.03 _cell_measurement_theta_max 24.65 _exptl_crystal_description needle _exptl_crystal_colour purple _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.275 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1124 _exptl_absorpt_coefficient_mu 0.751 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7533 _exptl_absorpt_correction_T_max 0.9424 _exptl_absorpt_process_details ; Blessing, R. Acta Cryst. (1995) A51 33-38. Sheldrick, G. SADABS (Version 2.10) Bruker/Siemens area detector absorption and other corrections, University of Gottingen, Germany 2003. ; _exptl_special_details ; 2750 frames x 30 sec. @ 4.969 cm; 0.5 deg. steps in omega & phi ; _diffrn_ambient_temperature 123(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 43984 _diffrn_reflns_av_R_equivalents 0.0848 _diffrn_reflns_av_sigmaI/netI 0.0470 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 24.92 _reflns_number_total 4746 _reflns_number_gt 3420 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0376P)^2^+6.0642P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4746 _refine_ls_number_parameters 308 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0766 _refine_ls_R_factor_gt 0.0451 _refine_ls_wR_factor_ref 0.1183 _refine_ls_wR_factor_gt 0.1049 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.17487(7) 0.95112(6) 0.10418(6) 0.0296(2) Uani 1 1 d . . . Co1 Co 0.19622(4) 0.81366(3) 0.19048(3) 0.02143(13) Uani 1 1 d . . . N1 N 0.2243(2) 0.6878(2) 0.28443(18) 0.0224(6) Uani 1 1 d . . . N2 N 0.0770(2) 0.6331(2) 0.21494(18) 0.0238(7) Uani 1 1 d . . . N3 N 0.0725(2) 0.7225(2) 0.17360(19) 0.0235(7) Uani 1 1 d . . . N4 N 0.3732(2) 0.6857(2) 0.20103(18) 0.0238(7) Uani 1 1 d . . . N5 N 0.3288(2) 0.7529(2) 0.14626(19) 0.0242(7) Uani 1 1 d . . . O1 O 0.20055(18) 0.88223(18) 0.30522(15) 0.0280(6) Uani 1 1 d . . . O2 O 0.1824(2) 0.8706(2) 0.44932(17) 0.0439(7) Uani 1 1 d . . . C1 C 0.1898(3) 0.8344(3) 0.3760(3) 0.0304(9) Uani 1 1 d . . . C2 C 0.1824(3) 0.7217(3) 0.3680(2) 0.0284(9) Uani 1 1 d . . . H2A H 0.2201 0.6903 0.4163 0.034 Uiso 1 1 calc R . . H2B H 0.1107 0.7013 0.3720 0.034 Uiso 1 1 calc R . . C3 C 0.1747(3) 0.5998(3) 0.2491(2) 0.0256(8) Uani 1 1 d . . . H3A H 0.1652 0.5496 0.2950 0.031 Uiso 1 1 calc R . . H3B H 0.2159 0.5705 0.2023 0.031 Uiso 1 1 calc R . . C4 C -0.0129(3) 0.5855(3) 0.2133(2) 0.0248(8) Uani 1 1 d . . . C5 C -0.0787(3) 0.6467(3) 0.1686(2) 0.0288(9) Uani 1 1 d . . . H5A H -0.1480 0.6341 0.1564 0.035 Uiso 1 1 calc R . . C6 C -0.0237(3) 0.7309(3) 0.1449(2) 0.0245(8) Uani 1 1 d . . . C7 C 0.3827(3) 0.7489(3) 0.0731(2) 0.0283(9) Uani 1 1 d . . . C8 C 0.4622(3) 0.6813(3) 0.0829(3) 0.0347(9) Uani 1 1 d . . . H8A H 0.5119 0.6654 0.0410 0.042 Uiso 1 1 calc R . . C9 C 0.4545(3) 0.6421(3) 0.1652(3) 0.0308(9) Uani 1 1 d . . . C10 C 0.3343(3) 0.6770(3) 0.2887(2) 0.0250(8) Uani 1 1 d . . . H10A H 0.3639 0.7291 0.3262 0.030 Uiso 1 1 calc R . . H10B H 0.3524 0.6116 0.3134 0.030 Uiso 1 1 calc R . . C11 C -0.0273(3) 0.4852(3) 0.2539(3) 0.0299(9) Uani 1 1 d . . . H11A H 0.0049 0.4867 0.3128 0.036 Uiso 1 1 calc R . . C12 C 0.0234(3) 0.4041(3) 0.2022(3) 0.0379(10) Uani 1 1 d . . . H12A H -0.0071 0.4007 0.1442 0.057 Uiso 1 1 calc R . . H12B H 0.0143 0.3405 0.2318 0.057 Uiso 1 1 calc R . . H12C H 0.0957 0.4185 0.1973 0.057 Uiso 1 1 calc R . . C13 C -0.1388(3) 0.4620(3) 0.2655(3) 0.0424(11) Uani 1 1 d . . . H13A H -0.1712 0.5161 0.2971 0.064 Uiso 1 1 calc R . . H13B H -0.1460 0.4003 0.2982 0.064 Uiso 1 1 calc R . . H13C H -0.1712 0.4547 0.2085 0.064 Uiso 1 1 calc R . . C14 C -0.0578(3) 0.8201(3) 0.0943(2) 0.0290(9) Uani 1 1 d . . . H14A H -0.0215 0.8793 0.1179 0.035 Uiso 1 1 calc R . . C15 C -0.1712(3) 0.8375(3) 0.1043(3) 0.0477(12) Uani 1 1 d . . . H15A H -0.2085 0.7816 0.0793 0.072 Uiso 1 1 calc R . . H15B H -0.1905 0.8985 0.0741 0.072 Uiso 1 1 calc R . . H15C H -0.1874 0.8435 0.1660 0.072 Uiso 1 1 calc R . . C16 C -0.0304(3) 0.8094(3) -0.0010(3) 0.0432(11) Uani 1 1 d . . . H16A H 0.0429 0.8012 -0.0063 0.065 Uiso 1 1 calc R . . H16B H -0.0517 0.8689 -0.0327 0.065 Uiso 1 1 calc R . . H16C H -0.0647 0.7514 -0.0254 0.065 Uiso 1 1 calc R . . C17 C 0.3550(3) 0.8108(3) -0.0046(2) 0.0329(9) Uani 1 1 d . . . H17A H 0.2829 0.8318 0.0015 0.040 Uiso 1 1 calc R . . C18 C 0.4193(4) 0.9025(3) -0.0076(3) 0.0563(13) Uani 1 1 d . . . H18A H 0.4058 0.9435 0.0434 0.084 Uiso 1 1 calc R . . H18B H 0.4032 0.9402 -0.0603 0.084 Uiso 1 1 calc R . . H18C H 0.4908 0.8837 -0.0080 0.084 Uiso 1 1 calc R . . C19 C 0.3641(4) 0.7509(4) -0.0893(3) 0.0528(13) Uani 1 1 d . . . H19A H 0.3454 0.7929 -0.1387 0.079 Uiso 1 1 calc R . . H19B H 0.3189 0.6936 -0.0871 0.079 Uiso 1 1 calc R . . H19C H 0.4340 0.7282 -0.0960 0.079 Uiso 1 1 calc R . . C20 C 0.5178(3) 0.5667(3) 0.2124(3) 0.0377(10) Uani 1 1 d . . . H20A H 0.4715 0.5247 0.2478 0.045 Uiso 1 1 calc R . . C22 C 0.5719(4) 0.4993(4) 0.1484(4) 0.0678(16) Uani 1 1 d . . . H22A H 0.5221 0.4681 0.1098 0.102 Uiso 1 1 calc R . . H22B H 0.6091 0.4480 0.1802 0.102 Uiso 1 1 calc R . . H22C H 0.6193 0.5385 0.1139 0.102 Uiso 1 1 calc R . . C23 C 0.5929(3) 0.6159(3) 0.2738(3) 0.0501(12) Uani 1 1 d . . . H23A H 0.6382 0.6588 0.2407 0.075 Uiso 1 1 calc R . . H23B H 0.6326 0.5650 0.3038 0.075 Uiso 1 1 calc R . . H23C H 0.5562 0.6556 0.3164 0.075 Uiso 1 1 calc R . . O3 O 0.2634(3) 1.0599(3) 0.4488(2) 0.0664(10) Uani 1 1 d . . . H3 H 0.2218 1.0160 0.4632 0.100 Uiso 1 1 calc R . . C24 C 0.3505(4) 1.0487(4) 0.4957(3) 0.0658(15) Uani 1 1 d . . . H24A H 0.3879 1.1114 0.4963 0.099 Uiso 1 1 calc R . . H24B H 0.3922 0.9971 0.4693 0.099 Uiso 1 1 calc R . . H24C H 0.3341 1.0297 0.5553 0.099 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0409(5) 0.0186(4) 0.0293(5) 0.0018(4) -0.0020(4) 0.0056(4) Co1 0.0241(2) 0.0182(2) 0.0219(3) 0.0005(2) -0.00029(18) 0.0014(2) N1 0.0191(14) 0.0241(15) 0.0239(16) 0.0028(13) -0.0001(12) -0.0030(13) N2 0.0199(15) 0.0244(16) 0.0268(17) 0.0040(13) -0.0034(12) 0.0000(13) N3 0.0265(16) 0.0187(15) 0.0252(16) 0.0006(13) -0.0020(13) 0.0030(12) N4 0.0250(15) 0.0201(15) 0.0264(16) 0.0055(13) 0.0001(13) 0.0023(13) N5 0.0269(16) 0.0206(15) 0.0253(17) 0.0050(13) 0.0017(13) 0.0014(13) O1 0.0343(14) 0.0261(13) 0.0235(14) 0.0000(11) 0.0038(11) -0.0022(11) O2 0.062(2) 0.0435(17) 0.0265(16) -0.0077(13) 0.0107(14) -0.0116(15) C1 0.0250(19) 0.034(2) 0.032(2) -0.0024(19) -0.0002(16) -0.0047(17) C2 0.031(2) 0.032(2) 0.022(2) 0.0028(16) -0.0010(16) -0.0048(17) C3 0.0222(18) 0.0265(19) 0.028(2) 0.0028(16) -0.0059(15) -0.0011(15) C4 0.0204(18) 0.0272(19) 0.027(2) -0.0056(16) 0.0010(15) -0.0002(15) C5 0.0205(18) 0.032(2) 0.034(2) -0.0063(17) -0.0035(16) 0.0028(16) C6 0.0253(19) 0.0254(19) 0.0227(19) -0.0070(16) -0.0025(15) 0.0050(16) C7 0.031(2) 0.0231(19) 0.031(2) 0.0006(16) 0.0048(17) -0.0020(16) C8 0.032(2) 0.032(2) 0.041(2) 0.0007(19) 0.0108(18) 0.0060(18) C9 0.0237(19) 0.028(2) 0.041(2) -0.0010(18) 0.0041(17) 0.0007(16) C10 0.0244(18) 0.0227(18) 0.028(2) 0.0069(16) -0.0041(15) -0.0041(15) C11 0.026(2) 0.031(2) 0.033(2) 0.0030(17) -0.0001(17) -0.0033(16) C12 0.032(2) 0.029(2) 0.054(3) -0.0009(19) -0.0002(19) -0.0019(17) C13 0.031(2) 0.042(2) 0.054(3) 0.001(2) 0.009(2) -0.0058(19) C14 0.031(2) 0.0259(19) 0.029(2) -0.0058(17) -0.0088(16) 0.0069(17) C15 0.036(2) 0.046(3) 0.061(3) 0.006(2) -0.005(2) 0.021(2) C16 0.058(3) 0.041(2) 0.030(2) 0.003(2) -0.007(2) 0.016(2) C17 0.042(2) 0.028(2) 0.029(2) 0.0030(18) 0.0107(17) 0.0058(18) C18 0.083(4) 0.046(3) 0.039(3) 0.004(2) 0.010(3) -0.010(3) C19 0.073(3) 0.048(3) 0.037(3) -0.001(2) 0.003(2) 0.000(3) C20 0.032(2) 0.030(2) 0.051(3) 0.0078(19) 0.0008(19) 0.0101(18) C22 0.070(4) 0.052(3) 0.081(4) -0.018(3) -0.022(3) 0.034(3) C23 0.042(3) 0.051(3) 0.058(3) 0.002(2) -0.010(2) 0.016(2) O3 0.077(3) 0.048(2) 0.074(2) 0.0075(18) -0.018(2) -0.0023(18) C24 0.069(4) 0.080(4) 0.048(3) 0.011(3) -0.017(3) -0.017(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 Co1 2.3009(10) . ? Co1 O1 1.998(2) . ? Co1 N5 2.057(3) . ? Co1 N3 2.063(3) . ? Co1 N1 2.263(3) . ? N1 C3 1.460(4) . ? N1 C10 1.464(4) . ? N1 C2 1.479(4) . ? N2 C4 1.351(4) . ? N2 N3 1.367(4) . ? N2 C3 1.463(4) . ? N3 C6 1.350(4) . ? N4 C9 1.348(5) . ? N4 N5 1.370(4) . ? N4 C10 1.456(4) . ? N5 C7 1.341(5) . ? O1 C1 1.278(4) . ? O2 C1 1.237(4) . ? C1 C2 1.530(5) . ? C4 C5 1.381(5) . ? C4 C11 1.506(5) . ? C5 C6 1.401(5) . ? C6 C14 1.502(5) . ? C7 C8 1.401(5) . ? C7 C17 1.505(5) . ? C8 C9 1.379(5) . ? C9 C20 1.504(5) . ? C11 C12 1.515(5) . ? C11 C13 1.520(5) . ? C14 C16 1.524(5) . ? C14 C15 1.528(5) . ? C17 C18 1.504(6) . ? C17 C19 1.542(6) . ? C20 C23 1.520(6) . ? C20 C22 1.525(6) . ? O3 C24 1.365(5) . ? 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 O1 Co1 N5 117.38(11) . . ? O1 Co1 N3 113.96(11) . . ? N5 Co1 N3 113.39(11) . . ? O1 Co1 N1 77.15(10) . . ? N5 Co1 N1 77.08(11) . . ? N3 Co1 N1 76.02(10) . . ? O1 Co1 Cl1 98.11(8) . . ? N5 Co1 Cl1 103.39(8) . . ? N3 Co1 Cl1 108.35(8) . . ? N1 Co1 Cl1 174.70(8) . . ? C3 N1 C10 112.3(3) . . ? C3 N1 C2 114.1(3) . . ? C10 N1 C2 111.7(3) . . ? C3 N1 Co1 107.5(2) . . ? C10 N1 Co1 105.2(2) . . ? C2 N1 Co1 105.3(2) . . ? C4 N2 N3 112.1(3) . . ? C4 N2 C3 129.5(3) . . ? N3 N2 C3 118.3(3) . . ? C6 N3 N2 105.4(3) . . ? C6 N3 Co1 137.4(2) . . ? N2 N3 Co1 115.9(2) . . ? C9 N4 N5 112.1(3) . . ? C9 N4 C10 129.4(3) . . ? N5 N4 C10 118.2(3) . . ? C7 N5 N4 105.3(3) . . ? C7 N5 Co1 139.0(2) . . ? N4 N5 Co1 115.0(2) . . ? C1 O1 Co1 121.3(2) . . ? O2 C1 O1 126.3(4) . . ? O2 C1 C2 117.5(3) . . ? O1 C1 C2 116.2(3) . . ? N1 C2 C1 110.8(3) . . ? N1 C3 N2 106.1(3) . . ? N2 C4 C5 106.1(3) . . ? N2 C4 C11 122.3(3) . . ? C5 C4 C11 131.6(3) . . ? C4 C5 C6 106.8(3) . . ? N3 C6 C5 109.6(3) . . ? N3 C6 C14 121.1(3) . . ? C5 C6 C14 129.2(3) . . ? N5 C7 C8 109.8(3) . . ? N5 C7 C17 121.3(3) . . ? C8 C7 C17 128.9(3) . . ? C9 C8 C7 106.8(3) . . ? N4 C9 C8 106.0(3) . . ? N4 C9 C20 122.7(3) . . ? C8 C9 C20 131.4(4) . . ? N4 C10 N1 108.0(3) . . ? C4 C11 C12 111.9(3) . . ? C4 C11 C13 111.1(3) . . ? C12 C11 C13 110.3(3) . . ? C6 C14 C16 110.7(3) . . ? C6 C14 C15 111.2(3) . . ? C16 C14 C15 110.7(3) . . ? C18 C17 C7 110.3(3) . . ? C18 C17 C19 111.0(3) . . ? C7 C17 C19 111.3(3) . . ? C9 C20 C23 111.3(3) . . ? C9 C20 C22 110.7(4) . . ? C23 C20 C22 110.9(4) . . ? 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 O3 H3 O2 0.84 2.04 2.772(4) 144.9 . _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 24.92 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.515 _refine_diff_density_min -0.345 _refine_diff_density_rms 0.072 #===END data_3 _database_code_depnum_ccdc_archive 'CCDC 690381' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H24 Co N6 O7' _chemical_formula_weight 447.32 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' O O 0.0106 0.0060 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' 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 14.7761(10) _cell_length_b 13.8389(9) _cell_length_c 9.6306(5) _cell_angle_alpha 90.00 _cell_angle_beta 99.293(4) _cell_angle_gamma 90.00 _cell_volume 1943.5(2) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 58401 _cell_measurement_theta_min 2.94 _cell_measurement_theta_max 25.68 _exptl_crystal_description parallelepiped _exptl_crystal_colour 'translucent light pink' _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.529 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 932 _exptl_absorpt_coefficient_mu 0.933 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.835 _exptl_absorpt_correction_T_max 0.894 _exptl_absorpt_process_details 'SCALEPACK (Otwinowski & Minor, 1997)' _exptl_special_details 'crystal-to-detector distance 30 mm' _diffrn_ambient_temperature 110(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 area-detector diffractometer' _diffrn_measurement_method 'two \f and three \w scans with 2\% steps' _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 58401 _diffrn_reflns_av_R_equivalents 0.0605 _diffrn_reflns_av_sigmaI/netI 0.0606 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.94 _diffrn_reflns_theta_max 25.68 _reflns_number_total 3656 _reflns_number_gt 3050 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'HKL2000 (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL2000 (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1999)' _computing_publication_material 'SHELXTL (Sheldrick, 1999); PLATON (Spek, 2003)' _refine_special_details ; Structure solved by Patterson map interpretation and subsequent Fourier-difference synthesis. All non-hydrogen atoms were refined with anisotropic displacement parameters. The H atoms bound to O3 and O7 were found on a Fourier-difference map and all the others were introduced at calculated positions. All were treated as riding atoms with an isotropic displacement parameter equal to 1.2 (OH, CH, CH~2~) or 1.5 (CH~3~) times that of the parent atom. 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^)+(0.0528P)^2^+7.2666P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary heavy _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3656 _refine_ls_number_parameters 257 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0747 _refine_ls_R_factor_gt 0.0635 _refine_ls_wR_factor_ref 0.1837 _refine_ls_wR_factor_gt 0.1787 _refine_ls_goodness_of_fit_ref 1.183 _refine_ls_restrained_S_all 1.183 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.576 _refine_diff_density_min -0.509 _refine_diff_density_rms 0.099 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 Co1 Co 0.72970(5) 0.16313(5) 0.47115(7) 0.0270(2) Uani 1 1 d . . . O1 O 0.7109(2) 0.2246(3) 0.2728(3) 0.0313(8) Uani 1 1 d . . . O2 O 0.7248(2) 0.1989(3) 0.0472(3) 0.0315(8) Uani 1 1 d . . . O3 O 0.7552(3) 0.1038(3) 0.6736(4) 0.0418(10) Uani 1 1 d . . . H3A H 0.7618 0.0418 0.7038 0.050 Uiso 1 1 d R . . H3B H 0.7869 0.1503 0.7372 0.050 Uiso 1 1 d R . . O4 O 0.7874(3) 0.9071(3) 0.7240(4) 0.0426(10) Uani 1 1 d . . . O5 O 0.7895(3) 0.8086(3) 0.9005(4) 0.0522(11) Uani 1 1 d . . . O6 O 0.8196(3) 0.9613(3) 0.9364(5) 0.0541(12) Uani 1 1 d . . . O7 O 0.7261(3) 0.6752(3) 0.6715(4) 0.0446(10) Uani 1 1 d . . . H7A H 0.7527 0.7352 0.7276 0.054 Uiso 1 1 d R . . H7B H 0.7493 0.6705 0.5925 0.054 Uiso 1 1 d R . . N1 N 0.7273(3) 0.0310(3) 0.3382(4) 0.0272(9) Uani 1 1 d . . . N2 N 0.8856(3) 0.0608(3) 0.3913(4) 0.0313(10) Uani 1 1 d . . . N3 N 0.8707(3) 0.1464(3) 0.4551(4) 0.0319(10) Uani 1 1 d . . . N4 N 0.5723(3) 0.0426(3) 0.3689(4) 0.0303(10) Uani 1 1 d . . . N5 N 0.5883(3) 0.1234(3) 0.4516(4) 0.0320(10) Uani 1 1 d . . . N6 N 0.7987(3) 0.8919(4) 0.8555(5) 0.0383(11) Uani 1 1 d . . . C1 C 0.7179(3) 0.1694(4) 0.1702(5) 0.0295(11) Uani 1 1 d . . . C2 C 0.7164(4) 0.0614(4) 0.1886(5) 0.0272(11) Uani 1 1 d . . . H2A H 0.6588 0.0364 0.1392 0.033 Uiso 1 1 calc R . . H2B H 0.7654 0.0331 0.1461 0.033 Uiso 1 1 calc R . . C3 C 0.8172(3) -0.0156(4) 0.3876(5) 0.0294(11) Uani 1 1 d . . . H3C H 0.8185 -0.0431 0.4805 0.035 Uiso 1 1 calc R . . H3D H 0.8286 -0.0666 0.3236 0.035 Uiso 1 1 calc R . . C4 C 0.9669(4) 0.0616(4) 0.3431(5) 0.0333(12) Uani 1 1 d . . . C5 C 1.0062(4) 0.1503(4) 0.3800(5) 0.0355(13) Uani 1 1 d . . . H5 H 1.0629 0.1721 0.3627 0.043 Uiso 1 1 calc R . . C6 C 0.9445(4) 0.2009(4) 0.4483(5) 0.0329(12) Uani 1 1 d . . . C7 C 0.4849(3) 0.0387(4) 0.3022(5) 0.0332(12) Uani 1 1 d . . . C8 C 0.4413(4) 0.1183(4) 0.3466(6) 0.0364(13) Uani 1 1 d . . . H8 H 0.3800 0.1353 0.3203 0.044 Uiso 1 1 calc R . . C9 C 0.5069(4) 0.1677(4) 0.4379(6) 0.0335(12) Uani 1 1 d . . . C10 C 0.6481(3) -0.0246(4) 0.3697(5) 0.0278(11) Uani 1 1 d . . . H10A H 0.6316 -0.0744 0.2993 0.033 Uiso 1 1 calc R . . H10B H 0.6629 -0.0552 0.4611 0.033 Uiso 1 1 calc R . . C11 C 0.9972(4) -0.0213(5) 0.2624(6) 0.0398(13) Uani 1 1 d . . . H11A H 1.0028 -0.0782 0.3202 0.060 Uiso 1 1 calc R . . H11B H 1.0554 -0.0066 0.2356 0.060 Uiso 1 1 calc R . . H11C H 0.9527 -0.0325 0.1796 0.060 Uiso 1 1 calc R . . C12 C 0.9508(4) 0.3015(4) 0.5054(6) 0.0407(14) Uani 1 1 d . . . H12A H 0.9075 0.3420 0.4471 0.061 Uiso 1 1 calc R . . H12B H 1.0116 0.3260 0.5063 0.061 Uiso 1 1 calc R . . H12C H 0.9371 0.3012 0.5995 0.061 Uiso 1 1 calc R . . C13 C 0.4479(4) -0.0410(5) 0.2014(6) 0.0409(14) Uani 1 1 d . . . H13A H 0.4880 -0.0498 0.1332 0.061 Uiso 1 1 calc R . . H13B H 0.3878 -0.0238 0.1543 0.061 Uiso 1 1 calc R . . H13C H 0.4446 -0.1000 0.2528 0.061 Uiso 1 1 calc R . . C14 C 0.4958(4) 0.2598(4) 0.5187(6) 0.0419(14) Uani 1 1 d . . . H14A H 0.4958 0.2446 0.6159 0.063 Uiso 1 1 calc R . . H14B H 0.4389 0.2903 0.4804 0.063 Uiso 1 1 calc R . . H14C H 0.5457 0.3028 0.5108 0.063 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.0313(4) 0.0275(4) 0.0229(3) 0.0005(3) 0.0060(3) 0.0000(3) O1 0.038(2) 0.031(2) 0.0258(17) -0.0034(16) 0.0106(14) -0.0002(17) O2 0.039(2) 0.027(2) 0.0289(18) 0.0041(16) 0.0086(15) 0.0002(16) O3 0.062(3) 0.033(2) 0.0296(19) 0.0049(17) 0.0051(18) 0.011(2) O4 0.045(2) 0.048(3) 0.036(2) 0.0042(19) 0.0092(17) -0.003(2) O5 0.080(3) 0.035(3) 0.043(2) 0.009(2) 0.015(2) -0.001(2) O6 0.073(3) 0.045(3) 0.047(2) -0.011(2) 0.016(2) -0.004(2) O7 0.053(3) 0.037(2) 0.045(2) 0.0005(19) 0.0110(19) -0.002(2) N1 0.025(2) 0.029(2) 0.028(2) 0.0033(18) 0.0060(16) 0.0001(18) N2 0.028(2) 0.033(3) 0.032(2) -0.002(2) 0.0036(18) -0.0001(19) N3 0.034(2) 0.030(2) 0.031(2) -0.0034(19) 0.0031(18) -0.002(2) N4 0.030(2) 0.029(2) 0.032(2) -0.0020(19) 0.0070(18) -0.0008(19) N5 0.034(2) 0.030(3) 0.034(2) -0.001(2) 0.0103(18) 0.001(2) N6 0.038(3) 0.038(3) 0.040(3) 0.001(2) 0.009(2) 0.006(2) C1 0.033(3) 0.033(3) 0.023(2) -0.002(2) 0.0042(19) 0.002(2) C2 0.033(3) 0.027(3) 0.022(2) -0.001(2) 0.0065(19) -0.002(2) C3 0.028(3) 0.028(3) 0.032(3) 0.001(2) 0.004(2) 0.000(2) C4 0.031(3) 0.041(3) 0.028(2) 0.003(2) 0.005(2) 0.002(2) C5 0.032(3) 0.043(4) 0.031(3) -0.001(2) 0.005(2) -0.001(2) C6 0.034(3) 0.034(3) 0.029(3) 0.003(2) 0.001(2) -0.003(2) C7 0.029(3) 0.039(3) 0.032(3) 0.004(2) 0.008(2) -0.004(2) C8 0.034(3) 0.041(4) 0.036(3) 0.006(3) 0.010(2) 0.000(2) C9 0.037(3) 0.030(3) 0.036(3) 0.005(2) 0.013(2) 0.003(2) C10 0.030(3) 0.026(3) 0.028(2) 0.001(2) 0.008(2) -0.002(2) C11 0.035(3) 0.045(4) 0.040(3) -0.005(3) 0.007(2) 0.003(3) C12 0.038(3) 0.035(3) 0.048(3) -0.002(3) 0.002(2) -0.009(3) C13 0.041(3) 0.044(4) 0.039(3) -0.003(3) 0.011(2) -0.007(3) C14 0.048(3) 0.038(3) 0.042(3) 0.002(3) 0.014(3) 0.007(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 O2 2.051(4) 4_566 ? Co1 O1 2.068(4) . ? Co1 O3 2.093(4) . ? Co1 N3 2.127(4) . ? Co1 N5 2.139(4) . ? Co1 N1 2.229(4) . ? O1 C1 1.267(6) . ? O2 C1 1.273(6) . ? O2 Co1 2.051(4) 4_565 ? O4 N6 1.268(6) . ? O5 N6 1.246(6) . ? O6 N6 1.244(6) . ? N1 C10 1.473(6) . ? N1 C3 1.483(6) . ? N1 C2 1.484(6) . ? N2 C4 1.355(7) . ? N2 N3 1.368(6) . ? N2 C3 1.460(7) . ? N3 C6 1.336(7) . ? N4 C7 1.347(7) . ? N4 N5 1.371(6) . ? N4 C10 1.455(7) . ? N5 C9 1.338(7) . ? C1 C2 1.505(7) . ? C4 C5 1.380(8) . ? C4 C11 1.494(8) . ? C5 C6 1.396(8) . ? C6 C12 1.494(8) . ? C7 C8 1.379(8) . ? C7 C13 1.512(8) . ? C8 C9 1.381(8) . ? C9 C14 1.516(8) . ? 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 O2 Co1 O1 86.53(14) 4_566 . ? O2 Co1 O3 92.53(15) 4_566 . ? O1 Co1 O3 177.17(16) . . ? O2 Co1 N3 102.66(16) 4_566 . ? O1 Co1 N3 87.96(15) . . ? O3 Co1 N3 89.64(17) . . ? O2 Co1 N5 100.39(16) 4_566 . ? O1 Co1 N5 92.36(15) . . ? O3 Co1 N5 90.43(17) . . ? N3 Co1 N5 156.92(18) . . ? O2 Co1 N1 166.10(14) 4_566 . ? O1 Co1 N1 79.61(15) . . ? O3 Co1 N1 101.36(15) . . ? N3 Co1 N1 78.10(16) . . ? N5 Co1 N1 79.27(16) . . ? C1 O1 Co1 117.2(3) . . ? C1 O2 Co1 130.1(3) . 4_565 ? C10 N1 C3 114.0(4) . . ? C10 N1 C2 112.5(4) . . ? C3 N1 C2 112.7(4) . . ? C10 N1 Co1 104.5(3) . . ? C3 N1 Co1 104.0(3) . . ? C2 N1 Co1 108.3(3) . . ? C4 N2 N3 111.3(4) . . ? C4 N2 C3 130.3(5) . . ? N3 N2 C3 118.5(4) . . ? C6 N3 N2 106.0(4) . . ? C6 N3 Co1 139.4(4) . . ? N2 N3 Co1 110.9(3) . . ? C7 N4 N5 111.9(4) . . ? C7 N4 C10 130.9(5) . . ? N5 N4 C10 117.2(4) . . ? C9 N5 N4 104.3(4) . . ? C9 N5 Co1 137.8(4) . . ? N4 N5 Co1 109.6(3) . . ? O6 N6 O5 121.8(5) . . ? O6 N6 O4 118.4(5) . . ? O5 N6 O4 119.8(5) . . ? O1 C1 O2 124.1(5) . . ? O1 C1 C2 120.2(4) . . ? O2 C1 C2 115.7(4) . . ? N1 C2 C1 113.2(4) . . ? N2 C3 N1 105.9(4) . . ? N2 C4 C5 106.2(5) . . ? N2 C4 C11 121.9(5) . . ? C5 C4 C11 131.9(5) . . ? C4 C5 C6 106.7(5) . . ? N3 C6 C5 109.9(5) . . ? N3 C6 C12 120.7(5) . . ? C5 C6 C12 129.4(5) . . ? N4 C7 C8 106.3(5) . . ? N4 C7 C13 123.7(5) . . ? C8 C7 C13 130.1(5) . . ? C7 C8 C9 106.1(5) . . ? N5 C9 C8 111.4(5) . . ? N5 C9 C14 120.3(5) . . ? C8 C9 C14 128.3(5) . . ? N4 C10 N1 107.6(4) . . ? 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 O3 H3B O1 0.96 2.12 2.680(5) 115.8 4_566 O3 H3A O4 0.91 1.91 2.792(6) 165.5 1_545 O7 H7A O5 1.03 1.95 2.913(6) 153.5 . O7 H7B O5 0.89 2.05 2.921(6) 166.4 4_575 #===END data_5 _database_code_depnum_ccdc_archive 'CCDC 690382' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H44 N10 O6 Zn2, 2(N O3), 2(H2 O)' _chemical_formula_sum 'C28 H48 N12 O14 Zn2' _chemical_formula_weight 907.52 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 9.3989(18) _cell_length_b 14.968(3) _cell_length_c 27.518(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.105(3) _cell_angle_gamma 90.00 _cell_volume 3871.4(13) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 9787 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 23.32 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.557 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1888 _exptl_absorpt_coefficient_mu 1.319 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6152 _exptl_absorpt_correction_T_max 0.6573 _exptl_absorpt_process_details ; Blessing, R. Acta Cryst. (1995) A51 33-38. Sheldrick, G. SADABS (Version 2.10) Bruker/Siemens area detector absorption and other corrections, University of Gottingen, Germany 2003. ; _exptl_special_details ; 2565 frames x 20 sec. @ 4.969 cm; 0.5 deg. steps in omega & phi ; _diffrn_ambient_temperature 123(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 77932 _diffrn_reflns_av_R_equivalents 0.0559 _diffrn_reflns_av_sigmaI/netI 0.0316 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 28.33 _reflns_number_total 9639 _reflns_number_gt 8684 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART-1K' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; The crystal was found to be a pseudo-merohedral twin, twin law (1 0 0, 0 -1 0, 0 0 -1) and refined scale factor BASF 0.361(2). DFIX restraints were applied to three O-H distances. The relatively less well ordered nitrates show somewhat larger displacements than the hydrogen bonded water solvate. 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^)+(0.0873P)^2^+12.0925P] 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 9639 _refine_ls_number_parameters 526 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0707 _refine_ls_R_factor_gt 0.0627 _refine_ls_wR_factor_ref 0.1726 _refine_ls_wR_factor_gt 0.1663 _refine_ls_goodness_of_fit_ref 1.105 _refine_ls_restrained_S_all 1.104 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.02101(7) 0.19975(4) 0.32876(2) 0.01998(13) Uani 1 1 d . . . Zn2 Zn -0.47670(6) 0.25928(3) 0.41884(2) 0.01917(13) Uani 1 1 d . . . O1 O 0.2248(4) 0.2187(3) 0.36057(13) 0.0243(7) Uani 1 1 d . . . O2 O 0.4532(4) 0.2547(2) 0.34938(13) 0.0235(8) Uani 1 1 d . . . O3 O -0.1855(4) 0.1845(3) 0.29930(14) 0.0231(7) Uani 1 1 d . . . H3A H -0.239(7) 0.208(4) 0.326(2) 0.028 Uiso 1 1 d . . . H3B H -0.209(9) 0.187(5) 0.269(3) 0.04(2) Uiso 1 1 d . . . O4 O -0.0470(4) 0.2072(3) 0.39808(13) 0.0236(8) Uani 1 1 d . . . O5 O -0.2733(4) 0.2449(2) 0.38621(13) 0.0210(7) Uani 1 1 d . . . O6 O -0.6795(4) 0.2699(3) 0.44885(14) 0.0257(8) Uani 1 1 d . . . H6A H -0.7380 0.2419 0.4314 0.031 Uiso 1 1 calc R . . H6B H -0.6823 0.2478 0.4786 0.031 Uiso 1 1 d R . . O7 O -0.5415(11) 0.2457(10) 0.6832(2) 0.180(7) Uani 1 1 d . . . O8 O -0.6906(8) 0.2078(5) 0.63030(19) 0.073(2) Uani 1 1 d . . . O9 O -0.4872(8) 0.2593(5) 0.6102(2) 0.080(2) Uani 1 1 d . . . O10 O -0.1141(11) 0.2276(6) 0.5908(3) 0.099(3) Uani 1 1 d . . . O11 O -0.066(2) 0.3332(7) 0.6360(3) 0.232(10) Uani 1 1 d . . . O12 O -0.0122(6) 0.3400(4) 0.56272(17) 0.0523(12) Uani 1 1 d . . . O13 O -0.7875(6) 0.2307(4) 0.53610(18) 0.0445(12) Uani 1 1 d D . . O14 O -0.2737(6) 0.2008(4) 0.20732(17) 0.0447(12) Uani 1 1 d D . . C1 C 0.0407(5) 0.4155(3) 0.3316(2) 0.0262(10) Uani 1 1 d . . . C2 C 0.1271(6) 0.4753(4) 0.3063(2) 0.0273(11) Uani 1 1 d . . . H2A H 0.1497 0.5348 0.3156 0.033 Uiso 1 1 calc R . . C3 C 0.1727(6) 0.4318(4) 0.2658(2) 0.0257(11) Uani 1 1 d . . . C4 C -0.0329(7) 0.4293(4) 0.3791(2) 0.0317(11) Uani 1 1 d . . . H4A H -0.0126 0.4896 0.3911 0.048 Uiso 1 1 calc R . . H4B H 0.0014 0.3852 0.4026 0.048 Uiso 1 1 calc R . . H4C H -0.1357 0.4222 0.3746 0.048 Uiso 1 1 calc R . . C5 C 0.2711(6) 0.4630(4) 0.2269(2) 0.0333(12) Uani 1 1 d . . . H5A H 0.3021 0.5242 0.2341 0.050 Uiso 1 1 calc R . . H5B H 0.2217 0.4619 0.1955 0.050 Uiso 1 1 calc R . . H5C H 0.3542 0.4236 0.2256 0.050 Uiso 1 1 calc R . . C6 C 0.1253(6) 0.2757(4) 0.23367(18) 0.0253(10) Uani 1 1 d . . . H6D H 0.1936 0.2901 0.2075 0.030 Uiso 1 1 calc R . . H6C H 0.0319 0.2620 0.2188 0.030 Uiso 1 1 calc R . . C7 C 0.1530(6) 0.1129(3) 0.23879(17) 0.0236(10) Uani 1 1 d . . . H7A H 0.0626 0.1134 0.2203 0.028 Uiso 1 1 calc R . . H7B H 0.2317 0.0996 0.2160 0.028 Uiso 1 1 calc R . . C8 C 0.1958(6) -0.0392(4) 0.27727(19) 0.0242(10) Uani 1 1 d . . . C9 C 0.1411(6) -0.0782(4) 0.31902(19) 0.0278(11) Uani 1 1 d . . . H9A H 0.1574 -0.1372 0.3304 0.033 Uiso 1 1 calc R . . C10 C 0.0570(5) -0.0124(4) 0.34089(19) 0.0279(11) Uani 1 1 d . . . C11 C 0.2936(6) -0.0755(4) 0.2398(2) 0.0303(11) Uani 1 1 d . . . H11A H 0.3117 -0.0297 0.2151 0.046 Uiso 1 1 calc R . . H11B H 0.2499 -0.1279 0.2244 0.046 Uiso 1 1 calc R . . H11C H 0.3836 -0.0930 0.2551 0.046 Uiso 1 1 calc R . . C12 C -0.0294(7) -0.0197(5) 0.3862(2) 0.0409(14) Uani 1 1 d . . . H12A H -0.0750 0.0378 0.3930 0.061 Uiso 1 1 calc R . . H12B H 0.0326 -0.0360 0.4135 0.061 Uiso 1 1 calc R . . H12C H -0.1026 -0.0657 0.3819 0.061 Uiso 1 1 calc R . . C13 C 0.3222(5) 0.2126(3) 0.28057(18) 0.0215(9) Uani 1 1 d . . . H13A H 0.3657 0.2635 0.2631 0.026 Uiso 1 1 calc R . . H13B H 0.3787 0.1586 0.2729 0.026 Uiso 1 1 calc R . . C14 C 0.3321(5) 0.2303(4) 0.33484(18) 0.0218(9) Uani 1 1 d . . . C15 C -0.4411(5) 0.4749(4) 0.41146(19) 0.0255(10) Uani 1 1 d . . . C16 C -0.3562(6) 0.5363(4) 0.4361(2) 0.0284(11) Uani 1 1 d . . . H16A H -0.3378 0.5963 0.4268 0.034 Uiso 1 1 calc R . . C17 C -0.3042(5) 0.4932(3) 0.47663(19) 0.0225(10) Uani 1 1 d . . . C18 C -0.5256(7) 0.4867(4) 0.3659(2) 0.0363(12) Uani 1 1 d . . . H18A H -0.5721 0.4302 0.3575 0.055 Uiso 1 1 calc R . . H18B H -0.4622 0.5048 0.3395 0.055 Uiso 1 1 calc R . . H18C H -0.5980 0.5329 0.3710 0.055 Uiso 1 1 calc R . . C19 C -0.2056(6) 0.5243(4) 0.5161(2) 0.0308(11) Uani 1 1 d . . . H19A H -0.1916 0.4761 0.5397 0.046 Uiso 1 1 calc R . . H19B H -0.2472 0.5763 0.5325 0.046 Uiso 1 1 calc R . . H19C H -0.1138 0.5410 0.5020 0.046 Uiso 1 1 calc R . . C20 C -0.3517(6) 0.3382(3) 0.51099(17) 0.0217(9) Uani 1 1 d . . . H20A H -0.4435 0.3345 0.5284 0.026 Uiso 1 1 calc R . . H20B H -0.2754 0.3502 0.5350 0.026 Uiso 1 1 calc R . . C21 C -0.3680(6) 0.1755(3) 0.51197(18) 0.0237(10) Uani 1 1 d . . . H21A H -0.4609 0.1860 0.5279 0.028 Uiso 1 1 calc R . . H21B H -0.2971 0.1602 0.5373 0.028 Uiso 1 1 calc R . . C22 C -0.3261(6) 0.0191(4) 0.47740(19) 0.0245(10) Uani 1 1 d . . . C23 C -0.3763(5) -0.0226(3) 0.4361(2) 0.0243(10) Uani 1 1 d . . . H23A H -0.3585 -0.0824 0.4262 0.029 Uiso 1 1 calc R . . C24 C -0.4584(5) 0.0409(3) 0.41179(18) 0.0231(10) Uani 1 1 d . . . C25 C -0.2262(6) -0.0116(4) 0.5157(2) 0.0336(12) Uani 1 1 d . . . H25A H -0.1991 -0.0738 0.5095 0.050 Uiso 1 1 calc R . . H25B H -0.2725 -0.0074 0.5475 0.050 Uiso 1 1 calc R . . H25C H -0.1409 0.0261 0.5155 0.050 Uiso 1 1 calc R . . C26 C -0.5329(7) 0.0306(3) 0.3642(2) 0.0310(11) Uani 1 1 d . . . H26A H -0.5842 0.0858 0.3564 0.046 Uiso 1 1 calc R . . H26B H -0.6005 -0.0191 0.3661 0.046 Uiso 1 1 calc R . . H26C H -0.4629 0.0183 0.3387 0.046 Uiso 1 1 calc R . . C27 C -0.1766(5) 0.2478(3) 0.46779(17) 0.0193(9) Uani 1 1 d . . . H27A H -0.1281 0.1986 0.4853 0.023 Uiso 1 1 calc R . . H27B H -0.1256 0.3039 0.4755 0.023 Uiso 1 1 calc R . . C28 C -0.1665(5) 0.2305(3) 0.41278(17) 0.0195(9) Uani 1 1 d . . . N1 N 0.0311(5) 0.3372(3) 0.30789(15) 0.0248(8) Uani 1 1 d . . . N2 N 0.1129(5) 0.3497(3) 0.26699(15) 0.0246(9) Uani 1 1 d . . . N3 N 0.1761(5) 0.1997(3) 0.26221(15) 0.0205(8) Uani 1 1 d . . . N4 N 0.1475(5) 0.0462(3) 0.27674(15) 0.0221(8) Uani 1 1 d . . . N5 N 0.0615(5) 0.0634(3) 0.31572(15) 0.0268(10) Uani 1 1 d . . . N6 N -0.4415(4) 0.3961(3) 0.43505(15) 0.0208(8) Uani 1 1 d . . . N7 N -0.3566(5) 0.4088(3) 0.47492(15) 0.0206(8) Uani 1 1 d . . . N8 N -0.3236(5) 0.2547(3) 0.48545(15) 0.0189(8) Uani 1 1 d . . . N9 N -0.3795(5) 0.1035(3) 0.47661(15) 0.0215(8) Uani 1 1 d . . . N10 N -0.4629(5) 0.1167(3) 0.43655(16) 0.0226(8) Uani 1 1 d . . . N11 N -0.5727(8) 0.2396(5) 0.6414(2) 0.0558(19) Uani 1 1 d . . . N12 N -0.0609(6) 0.3089(4) 0.60074(19) 0.0403(13) Uani 1 1 d . . . H14A H -0.224(9) 0.195(5) 0.178(3) 0.048 Uiso 1 1 d . . . H13C H -0.726(7) 0.241(5) 0.560(2) 0.048 Uiso 1 1 d D . . H13D H -0.881(3) 0.219(5) 0.535(3) 0.048 Uiso 1 1 d D . . H14B H -0.350(6) 0.219(5) 0.190(3) 0.048 Uiso 1 1 d 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 Zn1 0.0126(2) 0.0285(3) 0.0188(2) -0.00329(19) -0.0003(2) 0.0006(2) Zn2 0.0121(2) 0.0262(3) 0.0192(2) -0.0040(2) 0.0002(2) 0.0002(2) O1 0.0131(16) 0.039(2) 0.0204(16) -0.0024(15) -0.0004(13) -0.0002(15) O2 0.0176(19) 0.0301(18) 0.0229(16) -0.0020(13) -0.0004(14) -0.0007(14) O3 0.0139(16) 0.0323(19) 0.0231(17) -0.0030(15) -0.0045(13) -0.0007(14) O4 0.0118(17) 0.0362(19) 0.0228(16) -0.0031(14) -0.0004(13) 0.0032(13) O5 0.0103(15) 0.0312(18) 0.0216(16) -0.0013(13) -0.0001(13) 0.0021(13) O6 0.0144(16) 0.037(2) 0.0256(17) -0.0048(16) 0.0019(14) -0.0020(15) O7 0.114(7) 0.396(18) 0.028(3) -0.040(6) 0.018(4) -0.169(10) O8 0.069(4) 0.116(5) 0.032(3) -0.006(3) 0.004(3) -0.037(4) O9 0.079(5) 0.125(6) 0.037(3) 0.007(3) 0.033(3) -0.020(4) O10 0.125(8) 0.086(5) 0.088(5) 0.005(4) -0.007(6) -0.042(5) O11 0.49(3) 0.120(8) 0.083(5) -0.054(5) 0.136(11) -0.178(13) O12 0.052(3) 0.060(3) 0.045(2) 0.022(2) 0.006(2) 0.014(3) O13 0.043(3) 0.053(3) 0.038(2) 0.011(2) 0.014(2) 0.014(2) O14 0.049(3) 0.059(3) 0.026(2) -0.002(2) -0.005(2) 0.010(2) C1 0.021(2) 0.025(2) 0.033(2) -0.003(2) -0.004(2) 0.001(2) C2 0.024(2) 0.020(2) 0.038(3) 0.000(2) -0.004(2) 0.002(2) C3 0.020(2) 0.023(2) 0.034(3) 0.004(2) -0.002(2) 0.0061(19) C4 0.032(3) 0.025(2) 0.037(3) -0.009(2) 0.004(2) -0.005(2) C5 0.028(3) 0.027(3) 0.045(3) 0.009(2) 0.002(2) 0.002(2) C6 0.023(2) 0.031(3) 0.022(2) 0.003(2) -0.0041(19) 0.004(2) C7 0.024(2) 0.027(2) 0.019(2) -0.0025(19) -0.0001(18) 0.001(2) C8 0.020(2) 0.025(2) 0.027(2) -0.008(2) -0.0040(19) -0.0011(19) C9 0.022(2) 0.030(3) 0.032(3) 0.001(2) -0.0032(19) -0.004(2) C10 0.020(2) 0.037(3) 0.026(2) 0.000(2) -0.0012(18) -0.006(2) C11 0.028(3) 0.029(3) 0.034(3) -0.005(2) 0.005(2) 0.002(2) C12 0.029(3) 0.065(4) 0.029(3) 0.001(3) 0.008(2) -0.005(3) C13 0.015(2) 0.025(2) 0.024(2) -0.0018(18) -0.0006(18) 0.0018(18) C14 0.017(2) 0.028(2) 0.021(2) -0.003(2) -0.0019(18) 0.0034(19) C15 0.022(3) 0.027(2) 0.028(2) -0.001(2) 0.0006(19) 0.0060(18) C16 0.024(3) 0.027(3) 0.034(3) 0.001(2) 0.001(2) 0.010(2) C17 0.020(2) 0.018(2) 0.030(2) -0.0035(19) 0.0020(19) 0.0040(18) C18 0.035(3) 0.040(3) 0.033(3) 0.003(2) -0.004(3) 0.012(3) C19 0.026(3) 0.032(3) 0.035(3) -0.006(2) -0.003(2) 0.001(2) C20 0.025(2) 0.022(2) 0.018(2) -0.0054(18) 0.0002(17) 0.0023(19) C21 0.027(2) 0.024(2) 0.020(2) -0.0021(19) 0.0022(19) -0.010(2) C22 0.020(2) 0.025(2) 0.028(2) 0.008(2) 0.0010(19) -0.0026(19) C23 0.019(2) 0.017(2) 0.037(3) -0.0012(19) 0.001(2) -0.0017(18) C24 0.012(2) 0.028(2) 0.030(2) -0.0031(19) -0.0007(18) -0.0054(18) C25 0.023(3) 0.031(3) 0.047(3) 0.007(2) -0.003(2) -0.002(2) C26 0.030(3) 0.023(2) 0.040(3) -0.011(2) -0.011(2) -0.001(2) C27 0.016(2) 0.026(2) 0.016(2) -0.0037(17) 0.0009(17) -0.0007(17) C28 0.016(2) 0.023(2) 0.019(2) -0.0032(18) 0.0022(17) -0.0026(18) N1 0.0167(18) 0.032(2) 0.0256(19) -0.0102(17) 0.0001(17) 0.0032(18) N2 0.023(2) 0.027(2) 0.025(2) 0.0027(17) -0.0019(17) -0.0012(17) N3 0.0167(19) 0.028(2) 0.0170(18) -0.0029(16) -0.0060(16) 0.0029(15) N4 0.021(2) 0.026(2) 0.0191(18) -0.0019(16) 0.0015(16) 0.0008(17) N5 0.018(2) 0.043(3) 0.0196(19) -0.0040(18) 0.0040(15) -0.0030(18) N6 0.021(2) 0.0177(18) 0.0235(19) -0.0058(15) -0.0042(15) 0.0044(15) N7 0.023(2) 0.0160(18) 0.0226(19) -0.0030(15) -0.0039(16) 0.0019(16) N8 0.019(2) 0.0169(19) 0.0207(19) -0.0017(15) 0.0036(16) -0.0001(14) N9 0.023(2) 0.0173(19) 0.0240(19) -0.0003(15) 0.0003(17) -0.0038(16) N10 0.022(2) 0.0149(17) 0.031(2) 0.0022(15) 0.0007(18) -0.0022(17) N11 0.061(4) 0.078(5) 0.028(3) -0.012(3) 0.017(3) -0.027(3) N12 0.033(3) 0.059(4) 0.029(2) 0.005(2) -0.001(2) 0.007(2) _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 Zn1 O4 2.016(4) . ? Zn1 N5 2.107(5) . ? Zn1 O3 2.115(4) . ? Zn1 O1 2.124(4) . ? Zn1 N1 2.138(5) . ? Zn1 N3 2.343(4) . ? Zn2 O2 2.022(4) 1_455 ? Zn2 O6 2.085(4) . ? Zn2 N6 2.122(4) . ? Zn2 O5 2.125(4) . ? Zn2 N10 2.194(4) . ? Zn2 N8 2.330(4) . ? O1 C14 1.245(6) . ? O2 C14 1.260(6) . ? O2 Zn2 2.022(4) 1_655 ? O4 C28 1.244(6) . ? O5 C28 1.259(6) . ? O7 N11 1.189(9) . ? O8 N11 1.244(9) . ? O9 N11 1.213(8) . ? O10 N12 1.343(10) . ? O11 N12 1.038(9) . ? O12 N12 1.234(7) . ? C1 N1 1.344(6) . ? C1 C2 1.396(8) . ? C1 C4 1.493(7) . ? C2 C3 1.362(8) . ? C3 N2 1.351(7) . ? C3 C5 1.491(8) . ? C6 N2 1.443(7) . ? C6 N3 1.462(7) . ? C7 N4 1.446(6) . ? C7 N3 1.466(6) . ? C8 N4 1.356(7) . ? C8 C9 1.388(8) . ? C8 C11 1.485(7) . ? C9 C10 1.399(8) . ? C10 N5 1.330(7) . ? C10 C12 1.493(7) . ? C13 N3 1.474(6) . ? C13 C14 1.520(7) . ? C15 N6 1.346(7) . ? C15 C16 1.393(8) . ? C15 C18 1.493(8) . ? C16 C17 1.377(7) . ? C17 N7 1.357(6) . ? C17 C19 1.501(7) . ? C20 N7 1.451(6) . ? C20 N8 1.457(6) . ? C21 N8 1.454(6) . ? C21 N9 1.457(6) . ? C22 N9 1.359(7) . ? C22 C23 1.379(8) . ? C22 C25 1.484(7) . ? C23 C24 1.395(7) . ? C24 N10 1.324(6) . ? C24 C26 1.493(7) . ? C27 N8 1.469(6) . ? C27 C28 1.539(6) . ? N1 N2 1.377(6) . ? N4 N5 1.369(6) . ? N6 N7 1.369(5) . ? N9 N10 1.366(6) . ? 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 O4 Zn1 N5 105.82(16) . . ? O4 Zn1 O3 94.37(15) . . ? N5 Zn1 O3 89.78(16) . . ? O4 Zn1 O1 83.69(14) . . ? N5 Zn1 O1 92.10(16) . . ? O3 Zn1 O1 177.61(15) . . ? O4 Zn1 N1 102.42(15) . . ? N5 Zn1 N1 151.42(16) . . ? O3 Zn1 N1 92.42(16) . . ? O1 Zn1 N1 86.64(16) . . ? O4 Zn1 N3 159.80(14) . . ? N5 Zn1 N3 75.72(16) . . ? O3 Zn1 N3 105.81(14) . . ? O1 Zn1 N3 76.11(14) . . ? N1 Zn1 N3 76.26(15) . . ? O2 Zn2 O6 94.62(15) 1_455 . ? O2 Zn2 N6 106.40(15) 1_455 . ? O6 Zn2 N6 89.17(16) . . ? O2 Zn2 O5 83.63(15) 1_455 . ? O6 Zn2 O5 177.76(15) . . ? N6 Zn2 O5 92.65(15) . . ? O2 Zn2 N10 101.29(15) 1_455 . ? O6 Zn2 N10 92.28(17) . . ? N6 Zn2 N10 152.07(16) . . ? O5 Zn2 N10 86.71(15) . . ? O2 Zn2 N8 160.51(15) 1_455 . ? O6 Zn2 N8 104.75(15) . . ? N6 Zn2 N8 76.51(15) . . ? O5 Zn2 N8 76.95(14) . . ? N10 Zn2 N8 76.15(15) . . ? C14 O1 Zn1 121.0(3) . . ? C14 O2 Zn2 127.1(3) . 1_655 ? C28 O4 Zn1 127.7(3) . . ? C28 O5 Zn2 119.3(3) . . ? N1 C1 C2 110.9(5) . . ? N1 C1 C4 121.0(5) . . ? C2 C1 C4 128.2(5) . . ? C3 C2 C1 106.6(5) . . ? N2 C3 C2 106.5(5) . . ? N2 C3 C5 124.1(5) . . ? C2 C3 C5 129.4(5) . . ? N2 C6 N3 106.4(4) . . ? N4 C7 N3 107.5(4) . . ? N4 C8 C9 106.3(5) . . ? N4 C8 C11 123.0(5) . . ? C9 C8 C11 130.6(5) . . ? C8 C9 C10 105.7(5) . . ? N5 C10 C9 110.9(5) . . ? N5 C10 C12 121.0(5) . . ? C9 C10 C12 128.1(5) . . ? N3 C13 C14 114.5(4) . . ? O1 C14 O2 126.3(5) . . ? O1 C14 C13 119.1(4) . . ? O2 C14 C13 114.6(4) . . ? N6 C15 C16 110.2(5) . . ? N6 C15 C18 120.5(5) . . ? C16 C15 C18 129.3(5) . . ? C17 C16 C15 106.7(5) . . ? N7 C17 C16 106.2(5) . . ? N7 C17 C19 122.5(5) . . ? C16 C17 C19 131.2(5) . . ? N7 C20 N8 107.5(4) . . ? N8 C21 N9 106.8(4) . . ? N9 C22 C23 106.4(5) . . ? N9 C22 C25 122.2(5) . . ? C23 C22 C25 131.3(5) . . ? C22 C23 C24 105.9(5) . . ? N10 C24 C23 110.8(4) . . ? N10 C24 C26 121.7(5) . . ? C23 C24 C26 127.5(5) . . ? N8 C27 C28 113.4(4) . . ? O4 C28 O5 125.3(4) . . ? O4 C28 C27 115.1(4) . . ? O5 C28 C27 119.5(4) . . ? C1 N1 N2 104.0(4) . . ? C1 N1 Zn1 135.3(4) . . ? N2 N1 Zn1 112.1(3) . . ? C3 N2 N1 112.1(4) . . ? C3 N2 C6 130.4(5) . . ? N1 N2 C6 117.4(4) . . ? C6 N3 C7 113.9(4) . . ? C6 N3 C13 112.6(4) . . ? C7 N3 C13 113.8(4) . . ? C6 N3 Zn1 102.5(3) . . ? C7 N3 Zn1 104.6(3) . . ? C13 N3 Zn1 108.2(3) . . ? C8 N4 N5 111.6(4) . . ? C8 N4 C7 130.3(4) . . ? N5 N4 C7 117.2(4) . . ? C10 N5 N4 105.5(4) . . ? C10 N5 Zn1 137.0(4) . . ? N4 N5 Zn1 115.0(3) . . ? C15 N6 N7 105.3(4) . . ? C15 N6 Zn2 138.1(3) . . ? N7 N6 Zn2 113.1(3) . . ? C17 N7 N6 111.6(4) . . ? C17 N7 C20 130.1(4) . . ? N6 N7 C20 117.7(4) . . ? C21 N8 C20 113.8(4) . . ? C21 N8 C27 112.3(4) . . ? C20 N8 C27 113.1(4) . . ? C21 N8 Zn2 103.9(3) . . ? C20 N8 Zn2 104.0(3) . . ? C27 N8 Zn2 108.8(3) . . ? C22 N9 N10 111.0(4) . . ? C22 N9 C21 130.6(5) . . ? N10 N9 C21 118.3(4) . . ? C24 N10 N9 105.8(4) . . ? C24 N10 Zn2 136.2(4) . . ? N9 N10 Zn2 110.7(3) . . ? O7 N11 O9 120.2(8) . . ? O7 N11 O8 119.0(7) . . ? O9 N11 O8 120.7(7) . . ? O11 N12 O12 132.6(8) . . ? O11 N12 O10 119.4(8) . . ? O12 N12 O10 108.0(6) . . ? 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 O6 H6B O13 0.88 1.88 2.674(6) 147.7 . O13 H13C O8 0.89(2) 2.02(6) 2.767(8) 141(7) . O13 H13C O9 0.89(2) 2.65(3) 3.504(10) 163(7) . O13 H13D O12 0.90(2) 2.32(8) 2.771(7) 111(6) 1_455 O14 H14B O7 0.90(2) 1.89(4) 2.722(9) 154(8) 4_565 O14 H14B O7 0.90(2) 1.89(4) 2.722(9) 154(8) 4_565 O14 H14A O11 0.93(8) 1.94(8) 2.819(12) 157(7) 4_565 O3 H3A O5 0.96(7) 1.78(7) 2.688(5) 157(6) . O3 H3B O14 0.86(8) 1.82(8) 2.673(6) 174(8) . O6 H6A O1 0.84 2.01 2.700(5) 138.7 1_455 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.33 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.958 _refine_diff_density_min -1.081 _refine_diff_density_rms 0.142 #===END data_6 _database_code_depnum_ccdc_archive 'CCDC 690383' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H32 Co N8 O2' _chemical_formula_weight 463.46 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' O O 0.0106 0.0060 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 10.4185(6) _cell_length_b 14.8957(6) _cell_length_c 14.6449(9) _cell_angle_alpha 90.00 _cell_angle_beta 93.668(3) _cell_angle_gamma 90.00 _cell_volume 2268.1(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 29311 _cell_measurement_theta_min 3.07 _cell_measurement_theta_max 25.68 _exptl_crystal_description platelet _exptl_crystal_colour 'translucent light purple' _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.357 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 980 _exptl_absorpt_coefficient_mu 0.788 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.768 _exptl_absorpt_correction_T_max 0.882 _exptl_absorpt_process_details 'SCALEPACK (Otwinowski & Minor, 1997)' _exptl_special_details 'crystal-to-detector distance 30 mm' _diffrn_ambient_temperature 100(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 area-detector diffractometer' _diffrn_measurement_method 'two \f and two \w scans with 2\% steps' _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 29311 _diffrn_reflns_av_R_equivalents 0.0221 _diffrn_reflns_av_sigmaI/netI 0.0275 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 25.68 _reflns_number_total 4182 _reflns_number_gt 4028 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'HKL2000 (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL2000 (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1999)' _computing_publication_material 'SHELXTL (Sheldrick, 1999); PLATON (Spek, 2003)' _refine_special_details ; Structure solved by direct methods and subsequent Fourier-difference synthesis. All non-hydrogen atoms were refined with anisotropic displacement parameters. The H atoms bound to N atoms were found on a Fourier-difference map and all the others were introduced at calculated positions. All were treated as riding atoms with an isotropic displacement parameter equal to 1.2 (NH, CH, CH~2~) or 1.5 (CH~3~) times that of the parent atom. 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^)+(0.0424P)^2^+0.7685P] 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 constr _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 0.489(10) _refine_ls_number_reflns 4182 _refine_ls_number_parameters 278 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0289 _refine_ls_R_factor_gt 0.0273 _refine_ls_wR_factor_ref 0.0721 _refine_ls_wR_factor_gt 0.0713 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.226 _refine_diff_density_min -0.363 _refine_diff_density_rms 0.042 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 Co1 Co 0.790820(19) 0.234548(18) 0.158430(17) 0.02590(9) Uani 1 1 d . . . O1 O 0.80340(17) 0.36789(12) 0.12527(11) 0.0342(4) Uani 1 1 d . . . O2 O 0.89052(19) 0.29464(14) 0.01526(13) 0.0418(4) Uani 1 1 d . . . N1 N 0.89784(19) 0.12170(13) 0.15287(13) 0.0273(4) Uani 1 1 d . . . N2 N 1.00238(19) -0.00346(13) 0.12934(14) 0.0288(4) Uani 1 1 d . . . H2 H 1.0210 -0.0623 0.1024 0.035 Uiso 1 1 d R . . N3 N 0.9560(2) 0.25919(14) 0.27181(14) 0.0254(4) Uani 1 1 d . . . N4 N 0.6958(2) 0.24071(13) 0.27769(16) 0.0277(4) Uani 1 1 d . . . N5 N 0.5769(2) 0.23712(13) 0.39632(15) 0.0314(5) Uani 1 1 d . . . H5 H 0.5059 0.2220 0.4280 0.038 Uiso 1 1 d R . . N6 N 0.6360(2) 0.20483(16) 0.06578(14) 0.0336(5) Uani 1 1 d . . . N7 N 0.5668(2) 0.26735(13) 0.04923(14) 0.0282(5) Uani 1 1 d . . . N8 N 0.4959(2) 0.32704(15) 0.03286(16) 0.0415(5) Uani 1 1 d . . . C1 C 1.2859(2) 0.37696(18) 0.25866(17) 0.0358(6) Uani 1 1 d . . . H1A H 1.3149 0.3394 0.2109 0.054 Uiso 1 1 calc R . . H1B H 1.3563 0.3891 0.3024 0.054 Uiso 1 1 calc R . . H1C H 1.2537 0.4324 0.2329 0.054 Uiso 1 1 calc R . . C2 C 1.1795(2) 0.32952(17) 0.30583(16) 0.0317(5) Uani 1 1 d . . . H2A H 1.1468 0.3688 0.3518 0.038 Uiso 1 1 calc R . . H2B H 1.2138 0.2761 0.3364 0.038 Uiso 1 1 calc R . . C3 C 1.0695(2) 0.30317(16) 0.23629(16) 0.0266(5) Uani 1 1 d . . . H3A H 1.0405 0.3571 0.2040 0.032 Uiso 1 1 calc R . . H3B H 1.1043 0.2633 0.1917 0.032 Uiso 1 1 calc R . . C4 C 0.9849(2) 0.16769(14) 0.30754(15) 0.0269(5) Uani 1 1 d . . . H4A H 0.9213 0.1500 0.3497 0.032 Uiso 1 1 calc R . . H4B H 1.0689 0.1668 0.3401 0.032 Uiso 1 1 calc R . . C5 C 0.9824(2) 0.10411(15) 0.22850(15) 0.0262(5) Uani 1 1 d . . . C6 C 1.0473(2) 0.02642(15) 0.21495(15) 0.0276(5) Uani 1 1 d . . . C7 C 1.1430(2) -0.02314(17) 0.27489(18) 0.0366(6) Uani 1 1 d . . . H7A H 1.1743 0.0151 0.3242 0.055 Uiso 1 1 calc R . . H7B H 1.2135 -0.0413 0.2400 0.055 Uiso 1 1 calc R . . H7C H 1.1033 -0.0753 0.2993 0.055 Uiso 1 1 calc R . . C8 C 0.9132(2) 0.05513(15) 0.09388(16) 0.0278(5) Uani 1 1 d . . . C9 C 0.8455(3) 0.04547(17) 0.00135(17) 0.0335(5) Uani 1 1 d . . . H9A H 0.9071 0.0268 -0.0418 0.040 Uiso 1 1 calc R . . H9B H 0.8117 0.1035 -0.0183 0.040 Uiso 1 1 calc R . . C10 C 0.7359(3) -0.0218(2) -0.0010(2) 0.0469(7) Uani 1 1 d . . . H10A H 0.7677 -0.0788 0.0212 0.070 Uiso 1 1 calc R . . H10B H 0.7003 -0.0284 -0.0628 0.070 Uiso 1 1 calc R . . H10C H 0.6704 -0.0009 0.0370 0.070 Uiso 1 1 calc R . . C11 C 0.8961(2) 0.31515(14) 0.34110(15) 0.0267(5) Uani 1 1 d . . . H11A H 0.8912 0.3772 0.3210 0.032 Uiso 1 1 calc R . . H11B H 0.9471 0.3127 0.3988 0.032 Uiso 1 1 calc R . . C12 C 0.7643(2) 0.27932(15) 0.35272(16) 0.0269(5) Uani 1 1 d . . . C13 C 0.6923(2) 0.27712(15) 0.42731(17) 0.0289(5) Uani 1 1 d . . . C14 C 0.7193(3) 0.30694(18) 0.52389(17) 0.0379(6) Uani 1 1 d . . . H14A H 0.7988 0.3397 0.5289 0.057 Uiso 1 1 calc R . . H14B H 0.7258 0.2554 0.5633 0.057 Uiso 1 1 calc R . . H14C H 0.6508 0.3449 0.5417 0.057 Uiso 1 1 calc R . . C15 C 0.5834(2) 0.21577(15) 0.30751(17) 0.0303(5) Uani 1 1 d . . . C16 C 0.4786(2) 0.16621(17) 0.25393(18) 0.0343(5) Uani 1 1 d . . . H16A H 0.4602 0.1965 0.1959 0.041 Uiso 1 1 calc R . . H16B H 0.4011 0.1679 0.2873 0.041 Uiso 1 1 calc R . . C17 C 0.5132(3) 0.06876(17) 0.23576(19) 0.0385(6) Uani 1 1 d . . . H17A H 0.5886 0.0667 0.2015 0.058 Uiso 1 1 calc R . . H17B H 0.4430 0.0402 0.2015 0.058 Uiso 1 1 calc R . . H17C H 0.5297 0.0380 0.2929 0.058 Uiso 1 1 calc R . . C18 C 0.8504(2) 0.36663(16) 0.04741(16) 0.0301(5) Uani 1 1 d . . . C19 C 0.8607(3) 0.45384(19) -0.00276(19) 0.0428(6) Uani 1 1 d . . . H19A H 0.9218 0.4920 0.0302 0.064 Uiso 1 1 calc R . . H19B H 0.7782 0.4827 -0.0077 0.064 Uiso 1 1 calc R . . H19C H 0.8888 0.4426 -0.0629 0.064 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.02848(15) 0.02343(14) 0.02564(15) -0.00084(15) 0.00055(10) 0.00434(16) O1 0.0367(9) 0.0368(10) 0.0290(9) 0.0043(7) 0.0018(7) -0.0017(7) O2 0.0442(11) 0.0373(10) 0.0456(11) 0.0015(9) 0.0146(9) 0.0055(9) N1 0.0303(9) 0.0262(10) 0.0250(9) 0.0004(7) -0.0008(7) 0.0003(8) N2 0.0332(10) 0.0226(9) 0.0304(10) -0.0013(7) 0.0022(8) 0.0041(8) N3 0.0272(11) 0.0244(10) 0.0246(10) -0.0006(8) 0.0013(9) 0.0041(8) N4 0.0291(10) 0.0226(9) 0.0316(10) 0.0008(8) 0.0028(8) 0.0036(8) N5 0.0364(12) 0.0273(11) 0.0318(11) 0.0031(8) 0.0112(9) 0.0009(9) N6 0.0351(11) 0.0298(11) 0.0352(12) -0.0049(9) -0.0038(9) 0.0088(10) N7 0.0300(12) 0.0301(12) 0.0241(11) -0.0048(8) -0.0019(9) -0.0012(10) N8 0.0474(13) 0.0335(12) 0.0414(13) -0.0095(10) -0.0149(10) 0.0138(12) C1 0.0304(12) 0.0392(14) 0.0378(14) -0.0023(10) 0.0014(11) -0.0011(10) C2 0.0315(13) 0.0331(13) 0.0304(12) -0.0024(9) 0.0007(10) -0.0013(10) C3 0.0272(12) 0.0255(12) 0.0271(12) -0.0038(9) 0.0014(9) -0.0010(9) C4 0.0328(12) 0.0221(11) 0.0255(11) 0.0010(9) 0.0006(9) 0.0037(9) C5 0.0278(11) 0.0262(11) 0.0245(11) 0.0002(9) 0.0001(9) 0.0006(9) C6 0.0301(11) 0.0227(11) 0.0299(12) 0.0004(9) 0.0012(9) 0.0045(9) C7 0.0396(14) 0.0343(13) 0.0352(13) -0.0032(10) -0.0032(11) 0.0108(11) C8 0.0312(11) 0.0234(11) 0.0288(12) -0.0006(9) 0.0018(9) 0.0012(9) C9 0.0449(14) 0.0287(12) 0.0263(12) -0.0027(9) -0.0025(10) 0.0059(10) C10 0.0454(15) 0.0484(16) 0.0447(16) -0.0058(12) -0.0144(12) -0.0004(13) C11 0.0329(12) 0.0227(10) 0.0246(11) -0.0021(8) 0.0031(9) 0.0024(9) C12 0.0293(12) 0.0240(11) 0.0276(12) 0.0022(8) 0.0032(9) 0.0042(9) C13 0.0318(12) 0.0239(12) 0.0314(13) 0.0025(9) 0.0054(10) 0.0043(9) C14 0.0441(15) 0.0399(14) 0.0306(13) 0.0002(10) 0.0098(11) 0.0000(12) C15 0.0315(12) 0.0232(11) 0.0368(14) 0.0060(10) 0.0054(10) 0.0046(10) C16 0.0282(12) 0.0356(13) 0.0394(14) 0.0021(10) 0.0048(10) 0.0004(10) C17 0.0379(13) 0.0322(13) 0.0450(15) -0.0024(11) 0.0007(11) -0.0033(11) C18 0.0268(11) 0.0295(12) 0.0343(13) 0.0030(10) 0.0041(10) 0.0039(9) C19 0.0510(16) 0.0414(15) 0.0357(14) 0.0098(11) 0.0006(12) -0.0021(12) _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 Co1 N1 2.022(2) . ? Co1 O1 2.0510(18) . ? Co1 N4 2.064(2) . ? Co1 N6 2.088(2) . ? Co1 N3 2.343(2) . ? O1 C18 1.269(3) . ? O2 C18 1.254(3) . ? N1 C8 1.331(3) . ? N1 C5 1.395(3) . ? N2 C8 1.354(3) . ? N2 C6 1.383(3) . ? N2 H2 0.9846 . ? N3 C3 1.475(3) . ? N3 C11 1.482(3) . ? N3 C4 1.484(3) . ? N4 C15 1.328(3) . ? N4 C12 1.395(3) . ? N5 C15 1.345(3) . ? N5 C13 1.391(3) . ? N5 H5 0.9268 . ? N6 N7 1.193(3) . ? N7 N8 1.171(3) . ? C1 C2 1.517(3) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.535(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.495(3) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.361(3) . ? C6 C7 1.483(3) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 C9 1.494(3) . ? C9 C10 1.518(4) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C12 1.493(3) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.365(3) . ? C13 C14 1.492(4) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 C16 1.498(4) . ? C16 C17 1.523(4) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 C19 1.500(4) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? 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 N1 Co1 O1 138.76(8) . . ? N1 Co1 N4 111.52(8) . . ? O1 Co1 N4 101.46(7) . . ? N1 Co1 N6 101.70(8) . . ? O1 Co1 N6 96.31(8) . . ? N4 Co1 N6 99.60(9) . . ? N1 Co1 N3 77.10(7) . . ? O1 Co1 N3 87.76(7) . . ? N4 Co1 N3 76.35(8) . . ? N6 Co1 N3 174.80(9) . . ? C18 O1 Co1 103.45(14) . . ? C8 N1 C5 106.22(19) . . ? C8 N1 Co1 137.28(16) . . ? C5 N1 Co1 116.50(15) . . ? C8 N2 C6 108.91(18) . . ? C8 N2 H2 124.6 . . ? C6 N2 H2 125.8 . . ? C3 N3 C11 111.97(19) . . ? C3 N3 C4 112.55(19) . . ? C11 N3 C4 111.10(18) . . ? C3 N3 Co1 112.87(14) . . ? C11 N3 Co1 104.51(14) . . ? C4 N3 Co1 103.24(15) . . ? C15 N4 C12 105.9(2) . . ? C15 N4 Co1 138.28(19) . . ? C12 N4 Co1 115.82(17) . . ? C15 N5 C13 108.7(2) . . ? C15 N5 H5 121.2 . . ? C13 N5 H5 129.9 . . ? N7 N6 Co1 113.48(18) . . ? N8 N7 N6 178.1(3) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C1 C2 C3 110.69(19) . . ? C1 C2 H2A 109.5 . . ? C3 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? C3 C2 H2B 109.5 . . ? H2A C2 H2B 108.1 . . ? N3 C3 C2 117.45(19) . . ? N3 C3 H3A 107.9 . . ? C2 C3 H3A 107.9 . . ? N3 C3 H3B 107.9 . . ? C2 C3 H3B 107.9 . . ? H3A C3 H3B 107.2 . . ? N3 C4 C5 108.42(19) . . ? N3 C4 H4A 110.0 . . ? C5 C4 H4A 110.0 . . ? N3 C4 H4B 110.0 . . ? C5 C4 H4B 110.0 . . ? H4A C4 H4B 108.4 . . ? C6 C5 N1 109.8(2) . . ? C6 C5 C4 131.9(2) . . ? N1 C5 C4 118.3(2) . . ? C5 C6 N2 105.28(19) . . ? C5 C6 C7 131.2(2) . . ? N2 C6 C7 123.50(19) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N1 C8 N2 109.8(2) . . ? N1 C8 C9 126.2(2) . . ? N2 C8 C9 123.9(2) . . ? C8 C9 C10 113.3(2) . . ? C8 C9 H9A 108.9 . . ? C10 C9 H9A 108.9 . . ? C8 C9 H9B 108.9 . . ? C10 C9 H9B 108.9 . . ? H9A C9 H9B 107.7 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N3 C11 C12 107.95(19) . . ? N3 C11 H11A 110.1 . . ? C12 C11 H11A 110.1 . . ? N3 C11 H11B 110.1 . . ? C12 C11 H11B 110.1 . . ? H11A C11 H11B 108.4 . . ? C13 C12 N4 109.9(2) . . ? C13 C12 C11 131.0(2) . . ? N4 C12 C11 119.0(2) . . ? C12 C13 N5 104.9(2) . . ? C12 C13 C14 132.2(2) . . ? N5 C13 C14 122.9(2) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N4 C15 N5 110.6(2) . . ? N4 C15 C16 126.4(2) . . ? N5 C15 C16 122.9(2) . . ? C15 C16 C17 112.9(2) . . ? C15 C16 H16A 109.0 . . ? C17 C16 H16A 109.0 . . ? C15 C16 H16B 109.0 . . ? C17 C16 H16B 109.0 . . ? H16A C16 H16B 107.8 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O2 C18 O1 120.5(2) . . ? O2 C18 C19 121.4(2) . . ? O1 C18 C19 118.1(2) . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? 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 N2 H2 N8 0.98 1.95 2.892(3) 159.9 3_545 N5 H5 O2 0.93 1.83 2.732(3) 165.1 4_455 #===END data_7 _database_code_depnum_ccdc_archive 'CCDC 690384' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H39 Co N5 O6' _chemical_formula_weight 528.51 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' O O 0.0106 0.0060 '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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P n a 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 21.3853(8) _cell_length_b 13.2816(5) _cell_length_c 9.9306(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2820.60(17) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 128731 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 25.68 _exptl_crystal_description parallelepiped _exptl_crystal_colour 'translucent light purple' _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.245 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1124 _exptl_absorpt_coefficient_mu 0.650 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.840 _exptl_absorpt_correction_T_max 0.943 _exptl_absorpt_process_details 'SCALEPACK (Otwinowski & Minor, 1997)' _exptl_special_details 'crystal-to-detector distance 30 mm' _diffrn_ambient_temperature 100(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 area-detector diffractometer' _diffrn_measurement_method 'two \f and eight \w scans with 2\% steps' _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 128731 _diffrn_reflns_av_R_equivalents 0.0433 _diffrn_reflns_av_sigmaI/netI 0.0237 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.56 _diffrn_reflns_theta_max 25.68 _reflns_number_total 5152 _reflns_number_gt 4734 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'HKL2000 (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL2000 (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1999)' _computing_publication_material 'SHELXTL (Sheldrick, 1999); PLATON (Spek, 2003)' _refine_special_details ; Structure solved by direct methods and subsequent Fourier-difference synthesis. The atoms C1 and C2 in the propyl chain are disordered over two positions which were refined with occupancy parameters constrained to sum to unity. The two water solvent molecules were affected with 0.5 occupancy parameters in order to retain acceptable displacement factors and to take into account the close contact between O6 and one of the atoms of the disordered chain. All non-hydrogen atoms were refined with anisotropic displacement parameters, with restraints on bond lengths and/or displacement parameters for the disordered atoms and those of the solvent molecules. The H atoms bound to N and O atoms were found on a Fourier-difference map, except the hydroxylic proton of the ethanol molecule, and all the others were introduced at calculated positions. All were treated as riding atoms with an isotropic displacement parameter equal to 1.2 (NH, OH, CH, CH~2~) or 1.5 (CH~3~) times that of the parent atom. 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^)+(0.1202P)^2^+1.8139P] 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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.017(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.45(3) _refine_ls_number_reflns 5152 _refine_ls_number_parameters 342 _refine_ls_number_restraints 42 _refine_ls_R_factor_all 0.0628 _refine_ls_R_factor_gt 0.0580 _refine_ls_wR_factor_ref 0.1683 _refine_ls_wR_factor_gt 0.1642 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.088 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.104 _refine_diff_density_min -0.517 _refine_diff_density_rms 0.097 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 Co1 Co 0.33854(2) 0.89652(4) 0.1459(3) 0.0303(2) Uani 1 1 d . . . O1 O 0.40807(14) 0.8635(2) 0.0146(4) 0.0370(7) Uani 1 1 d . . . O2 O 0.45950(19) 0.7582(3) -0.1168(5) 0.0554(11) Uani 1 1 d . . . O3 O 0.32254(15) 0.7516(2) 0.1825(4) 0.0343(7) Uani 1 1 d . . . O4 O 0.33068(15) 0.5892(2) 0.1363(6) 0.0411(8) Uani 1 1 d . . . N1 N 0.26933(17) 0.9544(3) 0.0290(5) 0.0333(8) Uani 1 1 d . A . N2 N 0.20608(19) 1.0298(3) -0.1092(5) 0.0428(9) Uani 1 1 d . A . H2 H 0.2011 1.0595 -0.1932 0.051 Uiso 1 1 d R . . N3 N 0.26324(17) 0.9300(3) 0.3034(5) 0.0323(8) Uani 1 1 d . A . N4 N 0.38103(17) 1.0032(3) 0.2574(5) 0.0348(8) Uani 1 1 d . A . N5 N 0.43614(19) 1.1255(3) 0.3474(5) 0.0412(9) Uani 1 1 d . A . H5 H 0.4717 1.1642 0.3658 0.049 Uiso 1 1 d R . . C1A C 0.3128(4) 0.7798(6) 0.6135(6) 0.054(2) Uani 0.690(11) 1 d PD A 1 H1A H 0.2733 0.7920 0.6566 0.081 Uiso 0.690(11) 1 d PR A 1 H1B H 0.3460 0.7882 0.6778 0.081 Uiso 0.690(11) 1 d PR A 1 H1C H 0.3136 0.7123 0.5789 0.081 Uiso 0.690(11) 1 d PR A 1 C2A C 0.3233(2) 0.8522(5) 0.4973(6) 0.0421(18) Uani 0.690(11) 1 d PD A 1 H2A H 0.3363 0.9171 0.5325 0.050 Uiso 0.690(11) 1 d PR A 1 H2B H 0.3556 0.8281 0.4367 0.050 Uiso 0.690(11) 1 d PR A 1 C1B C 0.2349(8) 0.7807(11) 0.6357(14) 0.051(5) Uani 0.310(11) 1 d PD A 2 H1D H 0.2045 0.7789 0.7069 0.076 Uiso 0.310(11) 1 d PR A 2 H1E H 0.2365 0.7162 0.5924 0.076 Uiso 0.310(11) 1 d PR A 2 H1F H 0.2752 0.7966 0.6724 0.076 Uiso 0.310(11) 1 d PR A 2 C2B C 0.2157(5) 0.8600(10) 0.5334(9) 0.041(4) Uani 0.310(11) 1 d PD A 2 H2C H 0.2137 0.9249 0.5758 0.049 Uiso 0.310(11) 1 d PR A 2 H2D H 0.1753 0.8450 0.4962 0.049 Uiso 0.310(11) 1 d PR A 2 C3 C 0.2627(2) 0.8623(4) 0.4188(4) 0.0450(12) Uani 1 1 d D . . H3A H 0.2314 0.8868 0.4815 0.054 Uiso 0.690(11) 1 d PR A . H3B H 0.2495 0.7959 0.3895 0.054 Uiso 0.690(11) 1 d PR . . H3C H 0.3028 0.8776 0.4570 0.054 Uiso 0.310(11) 1 d PR . . H3D H 0.2641 0.7972 0.3770 0.054 Uiso 0.310(11) 1 d PR . . C4 C 0.2034(2) 0.9195(4) 0.2288(6) 0.0378(10) Uani 1 1 d . . . H4A H 0.1702 0.9544 0.2764 0.045 Uiso 1 1 calc R A . H4B H 0.1920 0.8489 0.2219 0.045 Uiso 1 1 calc R . . C5 C 0.2112(2) 0.9635(4) 0.0907(6) 0.0373(10) Uani 1 1 d . A . C6 C 0.1712(2) 1.0102(4) 0.0077(6) 0.0425(11) Uani 1 1 d . . . C7 C 0.1043(3) 1.0395(6) 0.0192(8) 0.0692(18) Uani 1 1 d . A . H7A H 0.0816 1.0134 -0.0564 0.104 Uiso 1 1 calc R . . H7B H 0.1010 1.1116 0.0205 0.104 Uiso 1 1 calc R . . H7C H 0.0873 1.0125 0.1010 0.104 Uiso 1 1 calc R . . C8 C 0.2641(2) 0.9961(3) -0.0913(5) 0.0375(10) Uani 1 1 d . . . C9 C 0.3154(3) 1.0116(4) -0.1901(6) 0.0452(11) Uani 1 1 d . A . H9A H 0.2981 1.0145 -0.2804 0.054 Uiso 1 1 calc R . . H9B H 0.3442 0.9552 -0.1861 0.054 Uiso 1 1 calc R . . C10 C 0.3505(4) 1.1084(5) -0.1607(12) 0.080(2) Uani 1 1 d U . . H10A H 0.3303 1.1634 -0.2059 0.119 Uiso 1 1 calc R A . H10B H 0.3928 1.1025 -0.1922 0.119 Uiso 1 1 calc R . . H10C H 0.3505 1.1206 -0.0654 0.119 Uiso 1 1 calc R . . C11 C 0.2733(2) 1.0368(3) 0.3404(6) 0.0347(9) Uani 1 1 d . . . H11A H 0.2569 1.0489 0.4301 0.042 Uiso 1 1 calc R A . H11B H 0.2509 1.0799 0.2780 0.042 Uiso 1 1 calc R . . C12 C 0.3417(2) 1.0624(4) 0.3372(6) 0.0344(9) Uani 1 1 d . A . C13 C 0.3750(2) 1.1383(4) 0.3941(6) 0.0428(11) Uani 1 1 d . . . C14 C 0.3566(3) 1.2254(5) 0.4787(9) 0.0680(17) Uani 1 1 d . A . H14A H 0.3606 1.2863 0.4275 0.102 Uiso 1 1 calc R . . H14B H 0.3832 1.2287 0.5564 0.102 Uiso 1 1 calc R . . H14C H 0.3139 1.2175 0.5071 0.102 Uiso 1 1 calc R . . C15 C 0.4381(2) 1.0453(3) 0.2665(6) 0.0384(10) Uani 1 1 d . . . C16 C 0.4961(2) 1.0098(5) 0.1988(7) 0.0526(13) Uani 1 1 d . A . H16A H 0.4889 0.9429 0.1628 0.063 Uiso 1 1 calc R . . H16B H 0.5293 1.0049 0.2651 0.063 Uiso 1 1 calc R . . C17 C 0.5170(3) 1.0776(6) 0.0871(8) 0.0738(19) Uani 1 1 d . . . H17A H 0.4860 1.0780 0.0172 0.111 Uiso 1 1 calc R A . H17B H 0.5559 1.0536 0.0513 0.111 Uiso 1 1 calc R . . H17C H 0.5224 1.1447 0.1212 0.111 Uiso 1 1 calc R . . C18 C 0.4135(2) 0.7806(4) -0.0463(5) 0.0373(10) Uani 1 1 d . . . C19 C 0.3600(2) 0.7037(4) -0.0378(5) 0.0388(10) Uani 1 1 d . . . H19A H 0.3249 0.7291 -0.0896 0.047 Uiso 1 1 calc R . . H19B H 0.3737 0.6417 -0.0800 0.047 Uiso 1 1 calc R . . C20 C 0.33720(18) 0.6794(3) 0.1035(5) 0.0317(10) Uani 1 1 d . . . O5 O 0.5145(4) 0.5904(6) -0.2266(10) 0.060(2) Uani 0.50 1 d PU . . H5A H 0.5089 0.6567 -0.1979 0.072 Uiso 0.50 1 d PR . . H5B H 0.4806 0.5547 -0.1888 0.072 Uiso 0.50 1 d PR . . O6 O 0.6021(5) 0.5838(7) -0.4100(12) 0.078(3) Uani 0.50 1 d PU . . H6A H 0.5756 0.5698 -0.3533 0.094 Uiso 0.50 1 d PR . . H6B H 0.5878 0.5600 -0.4982 0.094 Uiso 0.50 1 d PR . . O7 O 0.4495(3) 0.4246(5) -0.1465(7) 0.0856(15) Uani 1 1 d U . . C21 C 0.4644(5) 0.3229(9) -0.1650(12) 0.124(4) Uani 1 1 d DU . . H21A H 0.4268 0.2849 -0.1845 0.149 Uiso 1 1 calc R . . H21B H 0.4829 0.2961 -0.0834 0.149 Uiso 1 1 calc R . . C22 C 0.5103(5) 0.3127(10) -0.2811(11) 0.127(4) Uani 1 1 d DU . . H22A H 0.5023 0.2510 -0.3284 0.191 Uiso 1 1 calc R . . H22B H 0.5522 0.3121 -0.2466 0.191 Uiso 1 1 calc R . . H22C H 0.5053 0.3686 -0.3415 0.191 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.0315(3) 0.0266(3) 0.0328(3) -0.0012(3) 0.0022(3) -0.00073(18) O1 0.0378(16) 0.0270(15) 0.0464(17) -0.0007(14) 0.0077(14) -0.0049(12) O2 0.056(2) 0.0353(18) 0.075(3) -0.0130(17) 0.038(2) -0.0082(15) O3 0.0432(16) 0.0290(15) 0.0308(17) -0.0014(11) 0.0068(12) -0.0007(12) O4 0.0496(17) 0.0295(15) 0.0442(19) 0.0016(18) 0.0093(18) -0.0024(11) N1 0.038(2) 0.0334(19) 0.0287(18) -0.0002(15) 0.0048(15) 0.0004(15) N2 0.046(2) 0.046(2) 0.037(2) 0.0050(17) -0.0080(18) 0.0003(18) N3 0.0315(18) 0.036(2) 0.0291(18) 0.0003(16) 0.0035(14) -0.0020(15) N4 0.0341(18) 0.0327(19) 0.0375(19) -0.0015(15) 0.0029(16) -0.0018(15) N5 0.040(2) 0.0327(19) 0.051(2) -0.0045(18) -0.0144(18) -0.0019(16) C1A 0.071(5) 0.052(5) 0.038(4) 0.006(3) -0.006(3) -0.004(4) C2A 0.053(4) 0.037(4) 0.036(4) -0.002(3) 0.000(3) -0.001(3) C1B 0.074(10) 0.049(9) 0.029(7) 0.014(8) 0.014(8) -0.017(7) C2B 0.053(9) 0.030(8) 0.040(8) -0.006(6) 0.000(7) 0.016(6) C3 0.069(3) 0.035(2) 0.030(2) 0.001(2) 0.010(2) -0.002(2) C4 0.031(2) 0.049(3) 0.034(2) -0.003(2) 0.0045(17) -0.0044(19) C5 0.034(2) 0.041(2) 0.037(2) -0.0019(19) 0.0001(18) -0.0045(19) C6 0.033(2) 0.053(3) 0.041(3) 0.004(2) -0.0047(19) -0.004(2) C7 0.038(3) 0.098(5) 0.072(4) 0.012(4) -0.002(3) 0.007(3) C8 0.044(2) 0.031(2) 0.037(2) -0.0038(19) 0.0026(19) -0.0002(18) C9 0.055(3) 0.044(3) 0.037(3) 0.011(2) 0.004(2) 0.003(2) C10 0.071(4) 0.060(4) 0.108(6) 0.000(4) 0.040(4) -0.004(3) C11 0.036(2) 0.033(2) 0.035(2) -0.0022(19) -0.0008(18) 0.0026(17) C12 0.039(2) 0.030(2) 0.035(2) -0.0005(18) 0.0003(17) 0.0027(17) C13 0.044(3) 0.043(3) 0.042(3) -0.005(2) -0.006(2) 0.002(2) C14 0.071(4) 0.054(4) 0.079(5) -0.019(3) -0.004(4) 0.000(3) C15 0.027(2) 0.036(2) 0.052(3) -0.003(2) -0.0057(18) -0.0027(17) C16 0.033(2) 0.053(3) 0.071(3) -0.008(3) -0.001(2) 0.002(2) C17 0.069(4) 0.082(4) 0.070(4) -0.013(4) 0.027(3) -0.010(4) C18 0.038(2) 0.037(2) 0.036(2) 0.005(2) 0.0070(19) -0.0009(18) C19 0.045(2) 0.036(2) 0.035(2) -0.0041(19) 0.009(2) -0.0098(19) C20 0.0273(19) 0.031(2) 0.037(2) 0.0032(17) 0.0007(15) -0.0010(15) O5 0.066(3) 0.048(3) 0.065(3) -0.012(2) 0.006(3) 0.021(2) O6 0.083(4) 0.063(3) 0.088(4) 0.003(3) 0.001(3) 0.022(3) O7 0.081(3) 0.079(2) 0.096(3) -0.015(2) -0.010(2) 0.010(2) C21 0.123(4) 0.120(4) 0.131(4) -0.008(3) 0.008(3) -0.006(3) C22 0.126(4) 0.126(5) 0.130(5) -0.012(3) 0.003(3) -0.004(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 O3 1.989(3) . ? Co1 N4 2.014(4) . ? Co1 O1 2.026(3) . ? Co1 N1 2.032(4) . ? Co1 N3 2.288(4) . ? O1 C18 1.261(6) . ? O2 C18 1.244(6) . ? O3 C20 1.277(6) . ? O4 C20 1.250(6) . ? N1 C8 1.322(6) . ? N1 C5 1.392(6) . ? N2 C8 1.331(6) . ? N2 C6 1.405(7) . ? N3 C3 1.457(6) . ? N3 C11 1.482(6) . ? N3 C4 1.486(6) . ? N4 C15 1.345(5) . ? N4 C12 1.398(6) . ? N5 C15 1.335(6) . ? N5 C13 1.398(7) . ? C1A C2A 1.5197(11) . ? C2A C3 1.5183(11) . ? C1B C2B 1.5197(11) . ? C2B C3 1.5193(11) . ? C4 C5 1.500(6) . ? C5 C6 1.339(7) . ? C6 C7 1.486(7) . ? C8 C9 1.487(7) . ? C9 C10 1.516(9) . ? C11 C12 1.502(6) . ? C12 C13 1.357(7) . ? C13 C14 1.483(8) . ? C15 C16 1.488(7) . ? C16 C17 1.497(10) . ? C18 C19 1.536(6) . ? C19 C20 1.520(6) . ? O7 C21 1.400(12) . ? C21 C22 1.520(16) . ? 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 O3 Co1 N4 131.17(15) . . ? O3 Co1 O1 91.95(12) . . ? N4 Co1 O1 100.07(14) . . ? O3 Co1 N1 110.18(14) . . ? N4 Co1 N1 112.11(15) . . ? O1 Co1 N1 104.40(15) . . ? O3 Co1 N3 86.69(14) . . ? N4 Co1 N3 78.78(14) . . ? O1 Co1 N3 176.87(14) . . ? N1 Co1 N3 78.72(14) . . ? C18 O1 Co1 124.4(3) . . ? C20 O3 Co1 124.9(3) . . ? C8 N1 C5 106.6(4) . . ? C8 N1 Co1 137.5(3) . . ? C5 N1 Co1 115.6(3) . . ? C8 N2 C6 108.8(4) . . ? C3 N3 C11 113.4(4) . . ? C3 N3 C4 109.1(4) . . ? C11 N3 C4 109.8(4) . . ? C3 N3 Co1 115.0(3) . . ? C11 N3 Co1 104.7(3) . . ? C4 N3 Co1 104.3(3) . . ? C15 N4 C12 105.9(4) . . ? C15 N4 Co1 137.6(3) . . ? C12 N4 Co1 115.9(3) . . ? C15 N5 C13 109.0(4) . . ? C3 C2A C1A 108.6(5) . . ? C3 C2B C1B 109.6(8) . . ? N3 C3 C2A 116.8(4) . . ? N3 C3 C2B 127.4(6) . . ? N3 C4 C5 108.9(4) . . ? C6 C5 N1 109.9(4) . . ? C6 C5 C4 132.2(5) . . ? N1 C5 C4 117.9(4) . . ? C5 C6 N2 104.8(4) . . ? C5 C6 C7 133.5(5) . . ? N2 C6 C7 121.7(5) . . ? N1 C8 N2 109.9(4) . . ? N1 C8 C9 126.3(4) . . ? N2 C8 C9 123.6(4) . . ? C8 C9 C10 110.8(5) . . ? N3 C11 C12 110.7(4) . . ? C13 C12 N4 109.8(4) . . ? C13 C12 C11 132.0(4) . . ? N4 C12 C11 118.1(4) . . ? C12 C13 N5 105.2(4) . . ? C12 C13 C14 132.5(5) . . ? N5 C13 C14 122.1(5) . . ? N5 C15 N4 110.1(4) . . ? N5 C15 C16 123.4(4) . . ? N4 C15 C16 126.5(4) . . ? C15 C16 C17 113.1(5) . . ? O2 C18 O1 123.5(4) . . ? O2 C18 C19 117.5(4) . . ? O1 C18 C19 119.0(4) . . ? C20 C19 C18 115.5(4) . . ? O4 C20 O3 122.1(5) . . ? O4 C20 C19 118.7(4) . . ? O3 C20 C19 119.1(4) . . ? O7 C21 C22 109.5(10) . . ? 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 N2 H2 O4 0.93 1.87 2.762(7) 161.1 4_554 N5 H5 O2 0.94 1.80 2.738(5) 174.2 2_675 O5 H5A O2 0.93 1.89 2.746(8) 150.8 . O5 H5B O7 0.94 1.90 2.723(12) 144.5 . O6 H6A O5 0.82 1.84 2.615(14) 158.3 . O6 H6B O7 0.98 1.69 2.596(13) 152.7 2_664