# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email jc671@cam.ac.uk _publ_contact_author_name 'Jack K. Clegg' loop_ _publ_author_name 'Jack Harrowfield' 'Jack K. Clegg' 'Yang Kim' 'Young Hoon Lee' 'Jean-Marie Lehn' 'Woo Taik' ; P.Thuery ; data_1 _database_code_depnum_ccdc_archive 'CCDC 845921' #TrackingRef 'combined_final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C5 H18 Cl3 N3 O' _chemical_formula_weight 242.57 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 9.4620(19) _cell_length_b 12.156(2) _cell_length_c 18.508(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2128.8(7) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7591 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 30.4 _exptl_crystal_description irregular _exptl_crystal_colour white _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.514 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1024 _exptl_absorpt_coefficient_mu 0.825 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details 'crystal-to-detector distance 60 mm' _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.76999 _diffrn_radiation_type 'synchrotron radiation' _diffrn_radiation_source 'synchrotron radiation' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'ADSC Quantum210' _diffrn_measurement_method 'two \f and two \w scans with 2\% steps' _diffrn_detector_area_resol_mean 0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 7591 _diffrn_reflns_av_R_equivalents 0.0615 _diffrn_reflns_av_sigmaI/netI 0.0416 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.48 _diffrn_reflns_theta_max 30.38 _reflns_number_total 2156 _reflns_number_gt 1967 _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 ; 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^)+(0.0934P)^2^+1.6062P] 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 2156 _refine_ls_number_parameters 113 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0545 _refine_ls_R_factor_gt 0.0512 _refine_ls_wR_factor_ref 0.1441 _refine_ls_wR_factor_gt 0.1403 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _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 0.06450(6) 0.77225(6) 0.33788(3) 0.0355(2) Uani 1 1 d . . . Cl2 Cl 0.74297(7) 0.01522(5) 0.27312(4) 0.0341(2) Uani 1 1 d . . . Cl3 Cl 0.78188(6) 0.00739(5) 0.49531(3) 0.0285(2) Uani 1 1 d . . . C1 C 0.5091(2) 0.76006(19) 0.39027(11) 0.0204(5) Uani 1 1 d . . . C2 C 0.6711(2) 0.75705(19) 0.39048(12) 0.0226(5) Uani 1 1 d . . . H2A H 0.7058 0.8172 0.4200 0.027 Uiso 1 1 calc R . . H2B H 0.7018 0.6889 0.4128 0.027 Uiso 1 1 calc R . . C3 C 0.4424(2) 0.6677(2) 0.34451(12) 0.0229(5) Uani 1 1 d . . . H3A H 0.3408 0.6785 0.3438 0.028 Uiso 1 1 calc R . . H3B H 0.4760 0.6752 0.2952 0.028 Uiso 1 1 calc R . . C4 C 0.4507(2) 0.8657(2) 0.35559(12) 0.0240(5) Uani 1 1 d . . . H4A H 0.4837 0.8696 0.3060 0.029 Uiso 1 1 calc R . . H4B H 0.3483 0.8610 0.3544 0.029 Uiso 1 1 calc R . . C5 C 0.4576(3) 0.74799(19) 0.46889(13) 0.0272(5) Uani 1 1 d . . . H5A H 0.3551 0.7491 0.4698 0.033 Uiso 1 1 calc R . . H5B H 0.4887 0.6777 0.4880 0.033 Uiso 1 1 calc R . . N1 N 0.4717(2) 0.55325(18) 0.36925(11) 0.0283(5) Uani 1 1 d . . . H1A H 0.5646 0.5436 0.3735 0.042 Uiso 1 1 calc R . . H1B H 0.4374 0.5057 0.3372 0.042 Uiso 1 1 calc R . . H1C H 0.4306 0.5421 0.4119 0.042 Uiso 1 1 calc R . . N2 N 0.7361(2) 0.76537(16) 0.31719(12) 0.0258(5) Uani 1 1 d . . . H2C H 0.7113 0.7071 0.2910 0.039 Uiso 1 1 calc R . . H2D H 0.8297 0.7676 0.3214 0.039 Uiso 1 1 calc R . . H2E H 0.7058 0.8264 0.2955 0.039 Uiso 1 1 calc R . . N3 N 0.4913(3) 0.96772(19) 0.39312(12) 0.0338(5) Uani 1 1 d . . . H3C H 0.4378 0.9762 0.4323 0.051 Uiso 1 1 calc R . . H3D H 0.4788 1.0248 0.3637 0.051 Uiso 1 1 calc R . . H3E H 0.5817 0.9638 0.4061 0.051 Uiso 1 1 calc R . . O3 O 0.5106(2) 0.83422(18) 0.51325(10) 0.0387(5) Uani 1 1 d . . . H3 H 0.5339 0.8091 0.5526 0.058 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 0.0210(3) 0.0591(5) 0.0266(4) 0.0050(2) 0.0011(2) -0.0034(2) Cl2 0.0386(4) 0.0216(4) 0.0421(4) 0.0012(2) -0.0127(2) 0.0000(2) Cl3 0.0222(4) 0.0295(4) 0.0337(4) 0.0034(2) -0.0007(2) -0.0001(2) C1 0.0177(10) 0.0212(12) 0.0222(11) -0.0006(8) -0.0002(8) 0.0002(7) C2 0.0183(11) 0.0231(12) 0.0264(11) -0.0003(8) -0.0042(8) 0.0003(8) C3 0.0202(10) 0.0256(12) 0.0230(10) -0.0019(8) -0.0009(8) -0.0026(8) C4 0.0203(10) 0.0243(13) 0.0273(10) 0.0006(8) -0.0023(8) 0.0032(8) C5 0.0333(13) 0.0252(13) 0.0231(11) -0.0014(8) 0.0055(9) -0.0031(10) N1 0.0265(10) 0.0214(12) 0.0371(11) -0.0042(8) 0.0043(8) -0.0033(8) N2 0.0178(9) 0.0242(12) 0.0353(11) -0.0009(8) 0.0032(8) -0.0008(7) N3 0.0463(14) 0.0189(12) 0.0362(12) 0.0025(9) -0.0090(9) -0.0013(9) O3 0.0519(13) 0.0407(12) 0.0235(8) -0.0024(8) -0.0023(8) -0.0081(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 C1 C2 1.533(3) . ? C1 C4 1.538(3) . ? C1 C3 1.541(3) . ? C1 C5 1.541(3) . ? C2 N2 1.493(3) . ? C3 N1 1.491(3) . ? C4 N3 1.473(3) . ? C5 O3 1.423(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 C2 C1 C4 112.36(18) . . ? C2 C1 C3 113.17(18) . . ? C4 C1 C3 103.36(18) . . ? C2 C1 C5 108.15(18) . . ? C4 C1 C5 111.09(19) . . ? C3 C1 C5 108.65(18) . . ? N2 C2 C1 114.06(18) . . ? N1 C3 C1 115.76(18) . . ? N3 C4 C1 114.35(18) . . ? O3 C5 C1 111.28(19) . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 30.38 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.695 _refine_diff_density_min -0.731 _refine_diff_density_rms 0.108 data_yk2 _database_code_depnum_ccdc_archive 'CCDC 845922' #TrackingRef 'combined_final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H26 N6 O2' _chemical_formula_weight 418.50 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/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 9.3644(5) _cell_length_b 15.8507(6) _cell_length_c 14.2272(7) _cell_angle_alpha 90.00 _cell_angle_beta 105.960(3) _cell_angle_gamma 90.00 _cell_volume 2030.38(17) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 63060 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 25.68 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.369 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 888 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type none _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 four \w scans with 2\% steps (419 frames)' _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 63060 _diffrn_reflns_av_R_equivalents 0.0325 _diffrn_reflns_av_sigmaI/netI 0.0369 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 25.68 _reflns_number_total 3857 _reflns_number_gt 3155 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 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 O 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 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^)+(0.0510P)^2^+0.5186P] 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 3857 _refine_ls_number_parameters 280 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0511 _refine_ls_R_factor_gt 0.0399 _refine_ls_wR_factor_ref 0.1081 _refine_ls_wR_factor_gt 0.1023 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _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 0.196 _refine_diff_density_min -0.222 _refine_diff_density_rms 0.043 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 O1 O 0.60059(12) 0.43031(6) 0.81509(7) 0.0338(3) Uani 1 1 d . . . H1 H 0.6801 0.4360 0.8729 0.041 Uiso 1 1 d R . . O2 O 0.33029(11) 0.06518(6) 0.47948(7) 0.0308(3) Uani 1 1 d . . . H2A H 0.4154 0.0971 0.4781 0.037 Uiso 1 1 d R . . H2B H 0.2895 0.1037 0.5157 0.037 Uiso 1 1 d R . . N1 N 0.24375(13) 0.37545(7) 0.56975(8) 0.0256(3) Uani 1 1 d . . . N2 N 0.45520(13) 0.38536(7) 0.49751(8) 0.0252(3) Uani 1 1 d . . . N3 N 0.37184(13) 0.24669(8) 0.53960(8) 0.0246(3) Uani 1 1 d . . . N4 N 0.24454(15) 0.42584(9) 0.32023(9) 0.0351(3) Uani 1 1 d . . . N5 N 0.58334(14) 0.17075(8) 0.46593(8) 0.0283(3) Uani 1 1 d . . . N6 N 0.16171(14) 0.15018(8) 0.59288(9) 0.0309(3) Uani 1 1 d . . . C1 C 0.31117(16) 0.42159(9) 0.50147(10) 0.0262(3) Uani 1 1 d . . . H1A H 0.3329 0.4786 0.5283 0.031 Uiso 1 1 calc R . . C2 C 0.43193(16) 0.29514(9) 0.47035(10) 0.0252(3) Uani 1 1 d . . . H2 H 0.3562 0.2934 0.4072 0.030 Uiso 1 1 calc R . . C3 C 0.22871(15) 0.28617(9) 0.53862(10) 0.0256(3) Uani 1 1 d . . . H3 H 0.1687 0.2861 0.4703 0.031 Uiso 1 1 calc R . . C4 C 0.34644(15) 0.38204(9) 0.66920(10) 0.0257(3) Uani 1 1 d . . . H4A H 0.3048 0.3522 0.7150 0.031 Uiso 1 1 calc R . . H4B H 0.3578 0.4408 0.6887 0.031 Uiso 1 1 calc R . . C5 C 0.55841(15) 0.39274(9) 0.59732(10) 0.0255(3) Uani 1 1 d . . . H5A H 0.5711 0.4518 0.6156 0.031 Uiso 1 1 calc R . . H5B H 0.6548 0.3703 0.5973 0.031 Uiso 1 1 calc R . . C6 C 0.47483(16) 0.25238(9) 0.63902(10) 0.0248(3) Uani 1 1 d . . . H6A H 0.5693 0.2272 0.6392 0.030 Uiso 1 1 calc R . . H6B H 0.4343 0.2210 0.6843 0.030 Uiso 1 1 calc R . . C7 C 0.49939(15) 0.34464(9) 0.67286(10) 0.0249(3) Uani 1 1 d . . . C8 C 0.60443(16) 0.34885(9) 0.77512(10) 0.0276(3) Uani 1 1 d . . . H8A H 0.5757 0.3072 0.8164 0.033 Uiso 1 1 calc R . . H8B H 0.7047 0.3361 0.7728 0.033 Uiso 1 1 calc R . . C9 C 0.19796(17) 0.43192(9) 0.40206(10) 0.0285(3) Uani 1 1 d . . . C10 C 0.14359(19) 0.44294(10) 0.23416(11) 0.0367(4) Uani 1 1 d . . . H10 H 0.1739 0.4396 0.1772 0.044 Uiso 1 1 calc R . . C11 C -0.0005(2) 0.46487(11) 0.22621(12) 0.0421(4) Uani 1 1 d . . . H11 H -0.0662 0.4768 0.1656 0.051 Uiso 1 1 calc R . . C12 C -0.0458(2) 0.46871(14) 0.31062(13) 0.0536(5) Uani 1 1 d . . . H12 H -0.1433 0.4830 0.3074 0.064 Uiso 1 1 calc R . . C13 C 0.05347(19) 0.45136(12) 0.39950(12) 0.0432(4) Uani 1 1 d . . . H13 H 0.0237 0.4527 0.4567 0.052 Uiso 1 1 calc R . . C14 C 0.57097(16) 0.25473(9) 0.45440(10) 0.0258(3) Uani 1 1 d . . . C15 C 0.70290(16) 0.13308(10) 0.44934(10) 0.0299(3) Uani 1 1 d . . . H15 H 0.7134 0.0751 0.4588 0.036 Uiso 1 1 calc R . . C16 C 0.81106(17) 0.17594(10) 0.41900(10) 0.0319(3) Uani 1 1 d . . . H16 H 0.8920 0.1475 0.4082 0.038 Uiso 1 1 calc R . . C17 C 0.79543(17) 0.26225(11) 0.40512(11) 0.0334(4) Uani 1 1 d . . . H17 H 0.8652 0.2928 0.3837 0.040 Uiso 1 1 calc R . . C18 C 0.67459(17) 0.30260(10) 0.42353(10) 0.0298(3) Uani 1 1 d . . . H18 H 0.6628 0.3606 0.4154 0.036 Uiso 1 1 calc R . . C19 C 0.14283(15) 0.23400(10) 0.59506(10) 0.0278(3) Uani 1 1 d . . . C20 C 0.08328(17) 0.10125(11) 0.63778(12) 0.0368(4) Uani 1 1 d . . . H20 H 0.0953 0.0431 0.6361 0.044 Uiso 1 1 calc R . . C21 C -0.01408(18) 0.13276(12) 0.68622(12) 0.0411(4) Uani 1 1 d . . . H21 H -0.0644 0.0969 0.7179 0.049 Uiso 1 1 calc R . . C22 C -0.03502(18) 0.21915(12) 0.68648(12) 0.0397(4) Uani 1 1 d . . . H22 H -0.1012 0.2423 0.7176 0.048 Uiso 1 1 calc R . . C23 C 0.04360(16) 0.27097(11) 0.63987(11) 0.0331(4) Uani 1 1 d . . . H23 H 0.0303 0.3291 0.6386 0.040 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 O1 0.0385(6) 0.0291(6) 0.0285(5) -0.0048(4) 0.0006(4) 0.0033(5) O2 0.0340(6) 0.0263(6) 0.0303(5) -0.0014(4) 0.0059(4) -0.0028(4) N1 0.0273(6) 0.0253(6) 0.0241(6) -0.0005(5) 0.0071(5) 0.0008(5) N2 0.0292(6) 0.0224(6) 0.0237(6) -0.0012(5) 0.0066(5) -0.0004(5) N3 0.0253(6) 0.0245(6) 0.0247(6) 0.0009(5) 0.0078(5) -0.0005(5) N4 0.0403(8) 0.0373(8) 0.0273(7) -0.0005(6) 0.0086(6) -0.0058(6) N5 0.0320(7) 0.0260(7) 0.0269(6) -0.0031(5) 0.0083(5) -0.0006(5) N6 0.0287(7) 0.0303(7) 0.0329(7) 0.0026(6) 0.0071(5) -0.0042(5) C1 0.0308(8) 0.0226(7) 0.0245(7) 0.0001(6) 0.0066(6) 0.0017(6) C2 0.0290(7) 0.0232(7) 0.0236(7) 0.0002(6) 0.0076(6) -0.0003(6) C3 0.0252(7) 0.0257(7) 0.0251(7) -0.0004(6) 0.0056(6) 0.0000(6) C4 0.0284(8) 0.0255(8) 0.0223(7) 0.0001(6) 0.0056(6) 0.0010(6) C5 0.0267(7) 0.0239(7) 0.0252(7) -0.0012(6) 0.0060(6) -0.0003(6) C6 0.0261(7) 0.0238(7) 0.0248(7) 0.0020(6) 0.0077(6) 0.0005(6) C7 0.0265(7) 0.0238(7) 0.0242(7) -0.0004(6) 0.0064(6) 0.0005(6) C8 0.0286(8) 0.0262(8) 0.0266(7) -0.0013(6) 0.0050(6) 0.0014(6) C9 0.0344(8) 0.0223(7) 0.0273(7) 0.0003(6) 0.0062(6) 0.0007(6) C10 0.0475(10) 0.0353(9) 0.0256(7) -0.0007(7) 0.0070(7) -0.0101(7) C11 0.0545(11) 0.0319(9) 0.0297(8) 0.0020(7) -0.0054(7) 0.0050(8) C12 0.0369(10) 0.0711(14) 0.0468(10) -0.0063(10) 0.0015(8) 0.0242(9) C13 0.0374(9) 0.0606(12) 0.0302(8) -0.0007(8) 0.0072(7) 0.0194(8) C14 0.0296(8) 0.0255(8) 0.0222(7) -0.0029(6) 0.0065(6) -0.0011(6) C15 0.0347(8) 0.0266(8) 0.0283(7) -0.0042(6) 0.0084(6) 0.0032(6) C16 0.0302(8) 0.0386(9) 0.0273(7) -0.0040(6) 0.0088(6) 0.0033(7) C17 0.0324(8) 0.0380(9) 0.0327(8) -0.0019(7) 0.0140(6) -0.0043(7) C18 0.0355(8) 0.0260(8) 0.0293(7) 0.0003(6) 0.0113(6) -0.0003(6) C19 0.0242(7) 0.0317(8) 0.0262(7) 0.0001(6) 0.0047(6) -0.0026(6) C20 0.0331(8) 0.0351(9) 0.0418(9) 0.0054(7) 0.0094(7) -0.0067(7) C21 0.0331(9) 0.0481(11) 0.0441(9) 0.0072(8) 0.0140(7) -0.0092(7) C22 0.0323(8) 0.0523(11) 0.0379(9) -0.0006(8) 0.0154(7) -0.0025(8) C23 0.0302(8) 0.0376(9) 0.0317(8) -0.0003(7) 0.0088(6) -0.0006(7) _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 O1 C8 1.4152(17) . ? O1 H1 0.9497 . ? O2 H2A 0.9486 . ? O2 H2B 0.9448 . ? N1 C3 1.4780(18) . ? N1 C4 1.4797(17) . ? N1 C1 1.4880(18) . ? N2 C1 1.4812(18) . ? N2 C2 1.4818(18) . ? N2 C5 1.4864(17) . ? N3 C3 1.4758(18) . ? N3 C2 1.4771(17) . ? N3 C6 1.4795(17) . ? N4 C10 1.353(2) . ? N4 C9 1.3542(19) . ? N5 C14 1.3422(19) . ? N5 C15 1.3458(19) . ? N6 C19 1.342(2) . ? N6 C20 1.344(2) . ? C1 C9 1.5253(19) . ? C1 H1A 0.9800 . ? C2 C14 1.5230(19) . ? C2 H2 0.9800 . ? C3 C19 1.5266(19) . ? C3 H3 0.9800 . ? C4 C7 1.5377(19) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C7 1.5389(19) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.5371(19) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.5172(19) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C13 1.378(2) . ? C10 C11 1.368(2) . ? C10 H10 0.9300 . ? C11 C12 1.380(3) . ? C11 H11 0.9300 . ? C12 C13 1.376(2) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C18 1.395(2) . ? C15 C16 1.384(2) . ? C15 H15 0.9300 . ? C16 C17 1.384(2) . ? C16 H16 0.9300 . ? C17 C18 1.386(2) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 C23 1.393(2) . ? C20 C21 1.379(2) . ? C20 H20 0.9300 . ? C21 C22 1.383(3) . ? C21 H21 0.9300 . ? C22 C23 1.387(2) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? 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 C8 O1 H1 109.5 . . ? H2A O2 H2B 97.7 . . ? C3 N1 C4 109.71(11) . . ? C3 N1 C1 107.31(10) . . ? C4 N1 C1 107.98(11) . . ? C1 N2 C2 108.29(11) . . ? C1 N2 C5 107.03(10) . . ? C2 N2 C5 109.60(11) . . ? C3 N3 C2 106.55(11) . . ? C3 N3 C6 109.56(10) . . ? C2 N3 C6 109.77(11) . . ? C10 N4 C9 116.99(14) . . ? C14 N5 C15 117.81(13) . . ? C19 N6 C20 117.88(14) . . ? N2 C1 N1 112.86(11) . . ? N2 C1 C9 114.48(11) . . ? N1 C1 C9 110.28(11) . . ? N2 C1 H1A 106.2 . . ? N1 C1 H1A 106.2 . . ? C9 C1 H1A 106.2 . . ? N3 C2 N2 112.55(11) . . ? N3 C2 C14 112.26(11) . . ? N2 C2 C14 111.98(12) . . ? N3 C2 H2 106.5 . . ? N2 C2 H2 106.5 . . ? C14 C2 H2 106.5 . . ? N3 C3 N1 113.06(11) . . ? N3 C3 C19 111.95(11) . . ? N1 C3 C19 112.44(11) . . ? N3 C3 H3 106.3 . . ? N1 C3 H3 106.3 . . ? C19 C3 H3 106.3 . . ? N1 C4 C7 111.07(11) . . ? N1 C4 H4A 109.4 . . ? C7 C4 H4A 109.4 . . ? N1 C4 H4B 109.4 . . ? C7 C4 H4B 109.4 . . ? H4A C4 H4B 108.0 . . ? N2 C5 C7 111.35(11) . . ? N2 C5 H5A 109.4 . . ? C7 C5 H5A 109.4 . . ? N2 C5 H5B 109.4 . . ? C7 C5 H5B 109.4 . . ? H5A C5 H5B 108.0 . . ? N3 C6 C7 111.07(11) . . ? N3 C6 H6A 109.4 . . ? C7 C6 H6A 109.4 . . ? N3 C6 H6B 109.4 . . ? C7 C6 H6B 109.4 . . ? H6A C6 H6B 108.0 . . ? C8 C7 C6 110.12(11) . . ? C8 C7 C4 111.57(11) . . ? C6 C7 C4 107.36(11) . . ? C8 C7 C5 112.66(12) . . ? C6 C7 C5 107.71(11) . . ? C4 C7 C5 107.19(11) . . ? O1 C8 C7 110.12(11) . . ? O1 C8 H8A 109.6 . . ? C7 C8 H8A 109.6 . . ? O1 C8 H8B 109.6 . . ? C7 C8 H8B 109.6 . . ? H8A C8 H8B 108.2 . . ? N4 C9 C13 122.62(14) . . ? N4 C9 C1 118.91(13) . . ? C13 C9 C1 118.39(13) . . ? N4 C10 C11 123.63(15) . . ? N4 C10 H10 118.2 . . ? C11 C10 H10 118.2 . . ? C10 C11 C12 118.12(15) . . ? C10 C11 H11 120.9 . . ? C12 C11 H11 120.9 . . ? C13 C12 C11 119.95(16) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C12 C13 C9 118.64(15) . . ? C12 C13 H13 120.7 . . ? C9 C13 H13 120.7 . . ? N5 C14 C18 122.27(13) . . ? N5 C14 C2 116.58(12) . . ? C18 C14 C2 121.03(13) . . ? N5 C15 C16 123.55(14) . . ? N5 C15 H15 118.2 . . ? C16 C15 H15 118.2 . . ? C15 C16 C17 118.16(14) . . ? C15 C16 H16 120.9 . . ? C17 C16 H16 120.9 . . ? C16 C17 C18 119.27(14) . . ? C16 C17 H17 120.4 . . ? C18 C17 H17 120.4 . . ? C17 C18 C14 118.91(14) . . ? C17 C18 H18 120.5 . . ? C14 C18 H18 120.5 . . ? N6 C19 C23 122.42(14) . . ? N6 C19 C3 115.62(12) . . ? C23 C19 C3 121.81(14) . . ? N6 C20 C21 123.46(16) . . ? N6 C20 H20 118.3 . . ? C21 C20 H20 118.3 . . ? C20 C21 C22 118.27(15) . . ? C20 C21 H21 120.9 . . ? C22 C21 H21 120.9 . . ? C21 C22 C23 119.37(16) . . ? C21 C22 H22 120.3 . . ? C23 C22 H22 120.3 . . ? C22 C23 C19 118.57(16) . . ? C22 C23 H23 120.7 . . ? C19 C23 H23 120.7 . . ? 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 O1 H1 O2 0.95 1.76 2.7085(14) 173.9 4_666 O2 H2A N5 0.95 2.00 2.9502(16) 174.9 . O2 H2B N6 0.94 1.98 2.8828(16) 160.4 . data_3 _database_code_depnum_ccdc_archive 'CCDC 845923' #TrackingRef 'combined_final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H24 N6 O1, 3(H2 O)' _chemical_formula_sum 'C23 H30 N6 O4' _chemical_formula_weight 454.48 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 9.2160(18) _cell_length_b 13.813(3) _cell_length_c 17.342(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2207.6(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 9490 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 30.4 _exptl_crystal_description irregular _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.38 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.349 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type NONE _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details 'crystal-to-detector distance 60 mm' _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.76999 _diffrn_radiation_type 'synchrotron radiation' _diffrn_radiation_source 'synchrotron radiation' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'ADSC Quantum210' _diffrn_measurement_method 'two \f and two \w scans with 2\% steps' _diffrn_detector_area_resol_mean 0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 9490 _diffrn_reflns_av_R_equivalents 0.0682 _diffrn_reflns_av_sigmaI/netI 0.0622 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 30.36 _reflns_number_total 5181 _reflns_number_gt 5010 _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 ; 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^)+(0.1392P)^2^+0.4397P] 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(4) _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 0.9(12) _refine_ls_number_reflns 5181 _refine_ls_number_parameters 311 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0631 _refine_ls_R_factor_gt 0.0612 _refine_ls_wR_factor_ref 0.1687 _refine_ls_wR_factor_gt 0.1670 _refine_ls_goodness_of_fit_ref 0.990 _refine_ls_restrained_S_all 0.990 _refine_ls_shift/su_max 0.055 _refine_ls_shift/su_mean 0.003 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 C1 C 0.5337(2) 0.49545(13) 0.34976(10) 0.0204(3) Uani 1 1 d . . . H1 H 0.5222 0.4325 0.3752 0.024 Uiso 1 1 calc R . . C2 C 0.40134(19) 0.61312(12) 0.27564(10) 0.0186(3) Uani 1 1 d . . . H2 H 0.4518 0.6613 0.3073 0.022 Uiso 1 1 calc R . . C3 C 0.6376(2) 0.56974(12) 0.23821(10) 0.0186(3) Uani 1 1 d . . . H3 H 0.6663 0.6217 0.2736 0.022 Uiso 1 1 calc R . . C4 C 0.4231(2) 0.42370(12) 0.20773(10) 0.0203(3) Uani 1 1 d . . . C5 C 0.5762(2) 0.39976(13) 0.23747(11) 0.0218(4) Uani 1 1 d . . . H5A H 0.5726 0.3411 0.2682 0.026 Uiso 1 1 calc R . . H5B H 0.6402 0.3882 0.1940 0.026 Uiso 1 1 calc R . . C6 C 0.4347(2) 0.51725(12) 0.16013(10) 0.0193(3) Uani 1 1 d . . . H6A H 0.4975 0.5064 0.1161 0.023 Uiso 1 1 calc R . . H6B H 0.3394 0.5351 0.1410 0.023 Uiso 1 1 calc R . . C7 C 0.3258(2) 0.44555(13) 0.27768(11) 0.0215(4) Uani 1 1 d . . . H7A H 0.2295 0.4629 0.2599 0.026 Uiso 1 1 calc R . . H7B H 0.3173 0.3879 0.3093 0.026 Uiso 1 1 calc R . . C8 C 0.2551(2) 0.65809(13) 0.25478(10) 0.0226(4) Uani 1 1 d . . . C9 C 0.1404(2) 0.65681(17) 0.30663(13) 0.0298(4) Uani 1 1 d . . . H9 H 0.1465 0.6211 0.3520 0.036 Uiso 1 1 calc R . . C10 C 0.0156(2) 0.71006(18) 0.28963(15) 0.0375(5) Uani 1 1 d . . . H10 H -0.0620 0.7115 0.3239 0.045 Uiso 1 1 calc R . . C11 C 0.0099(3) 0.76055(18) 0.22104(16) 0.0389(5) Uani 1 1 d . . . H11 H -0.0716 0.7969 0.2082 0.047 Uiso 1 1 calc R . . C12 C 0.1269(3) 0.75606(16) 0.17217(14) 0.0345(5) Uani 1 1 d . . . H12 H 0.1211 0.7890 0.1255 0.041 Uiso 1 1 calc R . . C13 C 0.7534(2) 0.56609(14) 0.17607(10) 0.0225(4) Uani 1 1 d . . . C14 C 0.8773(2) 0.51109(16) 0.18575(13) 0.0297(4) Uani 1 1 d . . . H14 H 0.8877 0.4712 0.2286 0.036 Uiso 1 1 calc R . . C15 C 0.9859(2) 0.5163(2) 0.13059(15) 0.0391(5) Uani 1 1 d . . . H15 H 1.0706 0.4804 0.1360 0.047 Uiso 1 1 calc R . . C16 C 0.9663(3) 0.5757(2) 0.06751(13) 0.0399(6) Uani 1 1 d . . . H16 H 1.0382 0.5815 0.0301 0.048 Uiso 1 1 calc R . . C17 C 0.8382(3) 0.6263(2) 0.06110(13) 0.0384(5) Uani 1 1 d . . . H17 H 0.8240 0.6645 0.0176 0.046 Uiso 1 1 calc R . . C18 C 0.6019(2) 0.56263(13) 0.40914(10) 0.0209(4) Uani 1 1 d . . . C19 C 0.7506(2) 0.55687(15) 0.42316(11) 0.0261(4) Uani 1 1 d . . . H19 H 0.8088 0.5159 0.3939 0.031 Uiso 1 1 calc R . . C20 C 0.8108(2) 0.61316(16) 0.48137(13) 0.0302(4) Uani 1 1 d . . . H20 H 0.9097 0.6104 0.4918 0.036 Uiso 1 1 calc R . . C21 C 0.7208(3) 0.67343(16) 0.52350(12) 0.0295(4) Uani 1 1 d . . . H21 H 0.7579 0.7126 0.5624 0.035 Uiso 1 1 calc R . . C22 C 0.5735(2) 0.67404(15) 0.50628(11) 0.0275(4) Uani 1 1 d . . . H22 H 0.5132 0.7140 0.5352 0.033 Uiso 1 1 calc R . . C23 C 0.3692(2) 0.33761(13) 0.16089(12) 0.0252(4) Uani 1 1 d . . . H23A H 0.4400 0.3231 0.1211 0.030 Uiso 1 1 calc R . . H23B H 0.3630 0.2817 0.1945 0.030 Uiso 1 1 calc R . . N1 N 0.63439(17) 0.47977(11) 0.28468(9) 0.0196(3) Uani 1 1 d . . . N2 N 0.38577(17) 0.52580(11) 0.32488(9) 0.0194(3) Uani 1 1 d . . . N3 N 0.49392(16) 0.59698(11) 0.20800(8) 0.0183(3) Uani 1 1 d . . . N4 N 0.2494(2) 0.70682(12) 0.18772(10) 0.0268(4) Uani 1 1 d . . . N5 N 0.7324(2) 0.62350(14) 0.11451(10) 0.0292(4) Uani 1 1 d . . . N6 N 0.51350(19) 0.62012(12) 0.45013(9) 0.0239(3) Uani 1 1 d . . . O1 O 0.23238(17) 0.35211(11) 0.12553(9) 0.0294(3) Uani 1 1 d . . . H1A H 0.2433 0.3813 0.0848 0.044 Uiso 1 1 calc R . . O2 O 0.71458(19) 0.93474(14) 0.51398(9) 0.0391(4) Uani 1 1 d . . . O3 O 0.4796(3) 0.73453(13) 0.07530(10) 0.0468(5) Uani 1 1 d . . . O4 O 0.893(3) 0.8869(15) 0.0426(6) 0.058(4) Uani 0.33(4) 1 d P . . O4' O 0.822(3) 0.8665(6) 0.0401(3) 0.070(4) Uani 0.67(4) 1 d P . . 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 C1 0.0208(8) 0.0251(8) 0.0152(7) 0.0028(6) 0.0001(6) 0.0007(6) C2 0.0193(8) 0.0206(7) 0.0159(7) -0.0012(6) -0.0006(6) 0.0004(6) C3 0.0182(8) 0.0210(7) 0.0165(7) -0.0008(6) 0.0006(6) -0.0001(6) C4 0.0215(8) 0.0196(7) 0.0198(8) -0.0010(6) 0.0003(6) -0.0004(6) C5 0.0213(8) 0.0215(7) 0.0226(8) -0.0010(6) -0.0005(7) 0.0025(6) C6 0.0213(8) 0.0210(8) 0.0156(7) -0.0014(6) -0.0010(6) -0.0008(6) C7 0.0206(8) 0.0234(8) 0.0205(8) 0.0006(6) 0.0001(7) -0.0034(6) C8 0.0219(8) 0.0239(8) 0.0221(8) -0.0068(6) -0.0052(7) 0.0027(6) C9 0.0213(9) 0.0396(10) 0.0285(10) -0.0085(8) -0.0028(8) 0.0057(8) C10 0.0230(10) 0.0469(13) 0.0425(12) -0.0177(10) -0.0029(9) 0.0093(9) C11 0.0275(10) 0.0367(11) 0.0525(14) -0.0131(10) -0.0161(10) 0.0117(8) C12 0.0326(10) 0.0301(9) 0.0407(12) -0.0014(8) -0.0156(9) 0.0060(8) C13 0.0205(8) 0.0289(8) 0.0180(7) -0.0041(6) 0.0031(7) -0.0048(7) C14 0.0222(9) 0.0395(11) 0.0275(10) -0.0086(8) 0.0027(8) 0.0009(8) C15 0.0217(9) 0.0548(14) 0.0409(12) -0.0232(10) 0.0084(9) -0.0032(9) C16 0.0303(11) 0.0626(15) 0.0270(10) -0.0185(10) 0.0142(9) -0.0192(11) C17 0.0346(12) 0.0589(14) 0.0215(9) -0.0031(9) 0.0081(9) -0.0189(10) C18 0.0218(8) 0.0267(8) 0.0143(7) 0.0022(6) 0.0000(6) -0.0004(6) C19 0.0211(9) 0.0358(9) 0.0214(8) 0.0006(7) -0.0025(7) -0.0013(7) C20 0.0248(9) 0.0405(11) 0.0253(9) 0.0009(8) -0.0059(8) -0.0038(8) C21 0.0357(11) 0.0340(9) 0.0187(8) -0.0012(7) -0.0024(8) -0.0060(8) C22 0.0316(10) 0.0326(9) 0.0183(8) -0.0013(7) -0.0015(7) 0.0008(7) C23 0.0264(9) 0.0213(8) 0.0280(9) -0.0041(7) -0.0019(7) -0.0025(7) N1 0.0207(7) 0.0223(7) 0.0158(7) 0.0004(5) 0.0006(6) 0.0025(5) N2 0.0179(7) 0.0241(7) 0.0163(7) -0.0004(5) -0.0011(5) -0.0004(5) N3 0.0188(7) 0.0207(7) 0.0153(6) -0.0011(5) -0.0013(5) -0.0006(5) N4 0.0254(8) 0.0262(7) 0.0287(8) -0.0015(6) -0.0088(7) 0.0034(6) N5 0.0269(8) 0.0419(9) 0.0188(7) 0.0025(6) 0.0026(7) -0.0087(7) N6 0.0263(8) 0.0299(8) 0.0155(7) 0.0004(6) 0.0004(6) 0.0005(6) O1 0.0244(7) 0.0337(7) 0.0300(7) -0.0050(6) -0.0010(6) -0.0063(5) O2 0.0329(8) 0.0580(10) 0.0264(7) 0.0019(7) -0.0084(7) 0.0023(7) O3 0.0755(14) 0.0395(9) 0.0253(8) 0.0082(6) -0.0036(9) 0.0059(9) O4 0.055(9) 0.080(6) 0.039(4) 0.001(4) 0.006(4) 0.006(6) O4' 0.109(10) 0.052(3) 0.049(2) -0.0074(17) 0.007(3) 0.024(4) _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 C1 N1 1.477(2) . ? C1 N2 1.490(2) . ? C1 C18 1.522(2) . ? C2 N3 1.468(2) . ? C2 N2 1.485(2) . ? C2 C8 1.527(3) . ? C3 N3 1.473(2) . ? C3 N1 1.482(2) . ? C3 C13 1.517(2) . ? C4 C23 1.524(2) . ? C4 C6 1.537(2) . ? C4 C5 1.538(3) . ? C4 C7 1.538(3) . ? C5 N1 1.476(2) . ? C6 N3 1.483(2) . ? C7 N2 1.485(2) . ? C8 N4 1.345(3) . ? C8 C9 1.388(3) . ? C9 C10 1.396(3) . ? C10 C11 1.380(4) . ? C11 C12 1.373(4) . ? C12 N4 1.346(3) . ? C13 N5 1.344(3) . ? C13 C14 1.382(3) . ? C14 C15 1.387(3) . ? C15 C16 1.379(4) . ? C16 C17 1.377(4) . ? C17 N5 1.346(3) . ? C18 N6 1.342(2) . ? C18 C19 1.394(3) . ? C19 C20 1.390(3) . ? C20 C21 1.384(3) . ? C21 C22 1.389(3) . ? C22 N6 1.345(3) . ? C23 O1 1.416(2) . ? O4 O4' 0.721(10) . ? 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 C1 N2 113.25(13) . . ? N1 C1 C18 110.29(15) . . ? N2 C1 C18 113.73(15) . . ? N3 C2 N2 113.11(13) . . ? N3 C2 C8 112.67(14) . . ? N2 C2 C8 112.42(15) . . ? N3 C3 N1 112.95(14) . . ? N3 C3 C13 112.84(14) . . ? N1 C3 C13 111.86(14) . . ? C23 C4 C6 113.10(15) . . ? C23 C4 C5 108.07(15) . . ? C6 C4 C5 107.30(14) . . ? C23 C4 C7 112.54(15) . . ? C6 C4 C7 107.40(14) . . ? C5 C4 C7 108.21(15) . . ? N1 C5 C4 111.00(14) . . ? N3 C6 C4 110.43(13) . . ? N2 C7 C4 111.35(14) . . ? N4 C8 C9 122.47(18) . . ? N4 C8 C2 116.28(17) . . ? C9 C8 C2 120.90(17) . . ? C8 C9 C10 118.9(2) . . ? C11 C10 C9 118.7(2) . . ? C12 C11 C10 118.6(2) . . ? N4 C12 C11 123.9(2) . . ? N5 C13 C14 122.69(19) . . ? N5 C13 C3 116.30(17) . . ? C14 C13 C3 120.88(17) . . ? C13 C14 C15 119.0(2) . . ? C16 C15 C14 118.9(2) . . ? C17 C16 C15 118.6(2) . . ? N5 C17 C16 123.5(2) . . ? N6 C18 C19 122.59(18) . . ? N6 C18 C1 117.92(16) . . ? C19 C18 C1 119.30(17) . . ? C20 C19 C18 119.2(2) . . ? C21 C20 C19 118.7(2) . . ? C20 C21 C22 118.41(19) . . ? N6 C22 C21 123.65(19) . . ? O1 C23 C4 114.26(16) . . ? C5 N1 C1 107.77(14) . . ? C5 N1 C3 109.48(14) . . ? C1 N1 C3 107.77(13) . . ? C7 N2 C2 108.99(13) . . ? C7 N2 C1 106.87(14) . . ? C2 N2 C1 107.86(13) . . ? C2 N3 C3 106.09(13) . . ? C2 N3 C6 110.25(14) . . ? C3 N3 C6 109.90(13) . . ? C8 N4 C12 117.3(2) . . ? C13 N5 C17 117.4(2) . . ? C18 N6 C22 117.47(18) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.791 _refine_diff_density_min -0.274 _refine_diff_density_rms 0.080 data_4 _database_code_depnum_ccdc_archive 'CCDC 845924' #TrackingRef 'combined_final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H24 N6 O, H2 O' _chemical_formula_sum 'C23 H26 N6 O2' _chemical_formula_weight 418.50 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.4950(4) _cell_length_b 10.8560(5) _cell_length_c 10.8600(5) _cell_angle_alpha 86.974(3) _cell_angle_beta 66.316(3) _cell_angle_gamma 82.209(3) _cell_volume 1015.68(8) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5676 _cell_measurement_theta_min 2.43 _cell_measurement_theta_max 29.78 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.280 _exptl_crystal_size_mid 0.230 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.368 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 444 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6964 _exptl_absorpt_correction_T_max 0.7460 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2007)' _exptl_special_details ; The crystal was coated in Exxon Paratone N hydrocarbon oil and mounted on a thin mohair fibre attached to a copper pin. Upon mounting on the diffractometer, the crystal was quenched to 150(K) under a cold nitrogen gas stream supplied by an Oxford Cryosystems Cryostream and data were collected at this temperature. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type APEXII-FR591 _diffrn_measurement_method \w+\f _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 55430 _diffrn_reflns_av_R_equivalents 0.0468 _diffrn_reflns_av_sigmaI/netI 0.0383 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.84 _diffrn_reflns_theta_max 29.97 _reflns_number_total 5815 _reflns_number_gt 4215 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX (Bruker-Nonius, 2003)' _computing_cell_refinement 'SAINT (Bruker-Nonius, 2003)' _computing_data_reduction 'SAINT (Bruker-Nonius, 2003), XPREP (Bruker-Nonius, 2003)' _computing_structure_solution 'SIR97 (Altomare, et. al. 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ;ORTEP-3 (Farrugia, 1997) WINGX-32 (Farrugia, 1999) ; _computing_publication_material 'enCIFer 1.1 (CCDC, 2005)' _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^)+(0.0626P)^2^+0.2416P] 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 5815 _refine_ls_number_parameters 294 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0717 _refine_ls_R_factor_gt 0.0470 _refine_ls_wR_factor_ref 0.1282 _refine_ls_wR_factor_gt 0.1149 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _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 C1 C 0.6873(3) 0.3584(2) 0.4518(2) 0.0131(5) Uiso 0.50 1 d P A 1 H1A H 0.5954 0.3198 0.4597 0.016 Uiso 0.50 1 calc PR A 1 H1B H 0.6745 0.4458 0.4231 0.016 Uiso 0.50 1 calc PR A 1 C1A C 0.7324(4) 0.3262(3) 0.4461(3) 0.0221(6) Uiso 0.50 1 d P A 2 H1A1 H 0.8211 0.2601 0.4092 0.027 Uiso 0.50 1 calc PR A 2 H1A2 H 0.6402 0.2974 0.4413 0.027 Uiso 0.50 1 calc PR A 2 C2 C 0.70172(14) 0.35391(11) 0.59000(11) 0.0181(2) Uani 1 1 d . . . C3 C 0.70073(14) 0.22652(11) 0.65972(12) 0.0181(2) Uani 1 1 d . A . H3A H 0.6111 0.1872 0.6631 0.022 Uiso 1 1 calc R . . H3B H 0.7965 0.1717 0.6069 0.022 Uiso 1 1 calc R . . C4 C 0.83948(14) 0.41368(11) 0.59045(11) 0.0176(2) Uani 1 1 d . A . H4A H 0.9375 0.3619 0.5366 0.021 Uiso 1 1 calc R . . H4B H 0.8409 0.4969 0.5483 0.021 Uiso 1 1 calc R . . C5 C 0.55276(14) 0.43576(11) 0.67732(11) 0.0171(2) Uani 1 1 d . A . H5A H 0.5503 0.5191 0.6359 0.021 Uiso 1 1 calc R . . H5B H 0.4616 0.3984 0.6811 0.021 Uiso 1 1 calc R . . C6 C 0.82358(14) 0.30113(10) 0.79353(12) 0.0164(2) Uani 1 1 d . A . H6 H 0.8062 0.3151 0.8891 0.020 Uiso 1 1 calc R . . C7 C 0.98017(14) 0.22043(11) 0.73028(12) 0.0192(2) Uani 1 1 d . . . C8 C 1.11601(15) 0.27658(12) 0.67452(13) 0.0219(3) Uani 1 1 d . . . H8 H 1.1117 0.3646 0.6700 0.026 Uiso 1 1 calc R . . C11 C 1.12018(18) 0.02605(13) 0.69316(17) 0.0348(4) Uani 1 1 d . . . H11 H 1.1224 -0.0617 0.7000 0.042 Uiso 1 1 calc R . . C10 C 1.25973(17) 0.07387(13) 0.63536(15) 0.0305(3) Uani 1 1 d . . . H10 H 1.3551 0.0205 0.6029 0.037 Uiso 1 1 calc R . . C9 C 1.25716(16) 0.20156(13) 0.62594(14) 0.0272(3) Uani 1 1 d . . . H9 H 1.3512 0.2375 0.5866 0.033 Uiso 1 1 calc R . . C12 C 0.68088(13) 0.50206(10) 0.81029(11) 0.0139(2) Uani 1 1 d . A . H12 H 0.6743 0.5012 0.9045 0.017 Uiso 1 1 calc R . . C13 C 0.67933(14) 0.63804(10) 0.76620(11) 0.0161(2) Uani 1 1 d . . . C14 C 0.81488(15) 0.69427(11) 0.72140(12) 0.0203(3) Uani 1 1 d . . . H14 H 0.9108 0.6471 0.7112 0.024 Uiso 1 1 calc R . . C15 C 0.80726(17) 0.82053(12) 0.69190(13) 0.0276(3) Uani 1 1 d . . . H15 H 0.8980 0.8610 0.6609 0.033 Uiso 1 1 calc R . . C16 C 0.66541(18) 0.88645(12) 0.70837(14) 0.0306(3) Uani 1 1 d . . . H16 H 0.6569 0.9729 0.6891 0.037 Uiso 1 1 calc R . . C17 C 0.53662(17) 0.82390(12) 0.75338(14) 0.0269(3) Uani 1 1 d . . . H17 H 0.4396 0.8696 0.7645 0.032 Uiso 1 1 calc R . . C18 C 0.54912(13) 0.32434(10) 0.87705(11) 0.0143(2) Uani 1 1 d . A . H18 H 0.5557 0.3378 0.9649 0.017 Uiso 1 1 calc R . . C19 C 0.40082(14) 0.26580(11) 0.91139(11) 0.0168(2) Uani 1 1 d . . . C20 C 0.39921(15) 0.13887(12) 0.93718(12) 0.0222(3) Uani 1 1 d . . . H20 H 0.4928 0.0862 0.9233 0.027 Uiso 1 1 calc R . . C21 C 0.25849(17) 0.09029(13) 0.98368(14) 0.0296(3) Uani 1 1 d . . . H21 H 0.2544 0.0042 1.0032 0.035 Uiso 1 1 calc R . . C22 C 0.12509(17) 0.16914(14) 1.00091(14) 0.0301(3) Uani 1 1 d . . . H22 H 0.0276 0.1384 1.0320 0.036 Uiso 1 1 calc R . . C23 C 0.13651(15) 0.29420(13) 0.97190(13) 0.0265(3) Uani 1 1 d . . . H23 H 0.0445 0.3480 0.9834 0.032 Uiso 1 1 calc R . . N1 N 0.69104(11) 0.23964(9) 0.79810(10) 0.0155(2) Uani 1 1 d . . . N2 N 0.82877(11) 0.42592(8) 0.72953(9) 0.0147(2) Uani 1 1 d . . . N3 N 0.54363(11) 0.44873(8) 0.81577(9) 0.0144(2) Uani 1 1 d . . . N4 N 0.98077(14) 0.09634(10) 0.74059(13) 0.0303(3) Uani 1 1 d . . . N5 N 0.54107(13) 0.70141(9) 0.78248(10) 0.0209(2) Uani 1 1 d . . . N6 N 0.27105(12) 0.34371(10) 0.92833(10) 0.0206(2) Uani 1 1 d . . . O1 O 0.82455(19) 0.29246(15) 0.35464(15) 0.0176(3) Uani 0.50 1 d P A 1 H1O H 0.8167 0.2926 0.2803 0.026 Uiso 0.50 1 calc PR A 1 O1A O 0.7661(2) 0.43669(18) 0.37133(19) 0.0297(4) Uani 0.50 1 d P A 2 H2O H 0.7889 0.4223 0.2899 0.045 Uiso 0.50 1 calc PR A 2 O2 O 0.75986(12) 0.38844(10) 0.12922(9) 0.0260(2) Uani 1 1 d . . . H3O H 0.750(2) 0.4691(17) 0.1099(18) 0.039 Uiso 1 1 d . . . H4O H 0.664(2) 0.3675(16) 0.1547(17) 0.039 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C2 0.0213(6) 0.0189(6) 0.0138(5) 0.0000(4) -0.0050(4) -0.0083(5) C3 0.0175(6) 0.0151(5) 0.0192(6) -0.0035(4) -0.0035(4) -0.0044(4) C4 0.0183(6) 0.0165(5) 0.0141(5) -0.0006(4) -0.0013(4) -0.0053(4) C5 0.0200(6) 0.0159(5) 0.0185(6) 0.0040(4) -0.0102(5) -0.0052(4) C6 0.0134(6) 0.0138(5) 0.0208(6) 0.0010(4) -0.0056(4) -0.0020(4) C7 0.0149(6) 0.0171(6) 0.0247(6) -0.0007(5) -0.0073(5) -0.0002(4) C8 0.0172(6) 0.0209(6) 0.0267(6) 0.0003(5) -0.0076(5) -0.0030(5) C11 0.0274(8) 0.0192(7) 0.0551(10) -0.0033(6) -0.0154(7) 0.0047(5) C10 0.0196(7) 0.0313(7) 0.0356(8) -0.0060(6) -0.0087(6) 0.0085(5) C9 0.0156(7) 0.0347(7) 0.0294(7) -0.0008(6) -0.0070(5) -0.0034(5) C12 0.0137(6) 0.0133(5) 0.0140(5) -0.0006(4) -0.0048(4) -0.0019(4) C13 0.0210(6) 0.0137(5) 0.0132(5) -0.0012(4) -0.0062(4) -0.0019(4) C14 0.0225(7) 0.0179(6) 0.0188(6) -0.0015(4) -0.0059(5) -0.0042(5) C15 0.0344(8) 0.0200(6) 0.0258(7) 0.0005(5) -0.0068(6) -0.0122(5) C16 0.0460(9) 0.0140(6) 0.0292(7) 0.0034(5) -0.0126(6) -0.0040(6) C17 0.0326(8) 0.0166(6) 0.0304(7) 0.0009(5) -0.0138(6) 0.0039(5) C18 0.0132(6) 0.0148(5) 0.0134(5) 0.0011(4) -0.0040(4) -0.0012(4) C19 0.0142(6) 0.0214(6) 0.0129(5) 0.0004(4) -0.0030(4) -0.0042(4) C20 0.0216(7) 0.0200(6) 0.0221(6) 0.0027(5) -0.0049(5) -0.0058(5) C21 0.0319(8) 0.0282(7) 0.0279(7) 0.0041(5) -0.0077(6) -0.0164(6) C22 0.0223(7) 0.0431(8) 0.0253(7) 0.0016(6) -0.0057(5) -0.0175(6) C23 0.0148(7) 0.0390(8) 0.0246(6) -0.0017(5) -0.0060(5) -0.0050(5) N1 0.0125(5) 0.0144(5) 0.0180(5) -0.0001(4) -0.0043(4) -0.0014(4) N2 0.0143(5) 0.0128(4) 0.0151(5) -0.0008(3) -0.0038(4) -0.0014(3) N3 0.0143(5) 0.0130(4) 0.0162(5) 0.0015(4) -0.0064(4) -0.0025(4) N4 0.0210(6) 0.0169(5) 0.0496(8) -0.0004(5) -0.0113(5) 0.0002(4) N5 0.0253(6) 0.0157(5) 0.0218(5) 0.0001(4) -0.0104(4) 0.0005(4) N6 0.0138(5) 0.0264(5) 0.0198(5) -0.0005(4) -0.0048(4) -0.0027(4) O1 0.0168(9) 0.0226(8) 0.0103(7) -0.0052(6) -0.0043(6) 0.0062(6) O1A 0.0416(13) 0.0302(10) 0.0221(9) 0.0059(8) -0.0164(9) -0.0109(9) O2 0.0192(5) 0.0329(5) 0.0241(5) -0.0028(4) -0.0087(4) 0.0037(4) _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 C1 O1 1.430(3) . ? C1 C2 1.559(3) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C1A O1A 1.412(3) . ? C1A C2 1.509(3) . ? C1A H1A1 0.9900 . ? C1A H1A2 0.9900 . ? C2 C5 1.5362(17) . ? C2 C4 1.5388(17) . ? C2 C3 1.5406(16) . ? C3 N1 1.4816(15) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 N2 1.4843(15) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 N3 1.4840(14) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 N1 1.4853(15) . ? C6 N2 1.4873(14) . ? C6 C7 1.5297(16) . ? C6 H6 1.0000 . ? C7 N4 1.3453(16) . ? C7 C8 1.3958(17) . ? C8 C9 1.3854(18) . ? C8 H8 0.9500 . ? C11 N4 1.3490(18) . ? C11 C10 1.380(2) . ? C11 H11 0.9500 . ? C10 C9 1.382(2) . ? C10 H10 0.9500 . ? C9 H9 0.9500 . ? C12 N3 1.4749(15) . ? C12 N2 1.4822(14) . ? C12 C13 1.5277(15) . ? C12 H12 1.0000 . ? C13 N5 1.3451(16) . ? C13 C14 1.3944(17) . ? C14 C15 1.3900(17) . ? C14 H14 0.9500 . ? C15 C16 1.385(2) . ? C15 H15 0.9500 . ? C16 C17 1.380(2) . ? C16 H16 0.9500 . ? C17 N5 1.3494(16) . ? C17 H17 0.9500 . ? C18 N3 1.4776(14) . ? C18 N1 1.4885(14) . ? C18 C19 1.5237(16) . ? C18 H18 1.0000 . ? C19 N6 1.3488(16) . ? C19 C20 1.3925(17) . ? C20 C21 1.3925(18) . ? C20 H20 0.9500 . ? C21 C22 1.380(2) . ? C21 H21 0.9500 . ? C22 C23 1.386(2) . ? C22 H22 0.9500 . ? C23 N6 1.3485(17) . ? C23 H23 0.9500 . ? O1 H1O 0.8400 . ? O1A H2O 0.8400 . ? O2 H3O 0.891(18) . ? O2 H4O 0.89(2) . ? 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 C1 C2 108.78(19) . . ? O1 C1 H1A 109.9 . . ? C2 C1 H1A 109.9 . . ? O1 C1 H1B 109.9 . . ? C2 C1 H1B 109.9 . . ? H1A C1 H1B 108.3 . . ? O1A C1A C2 107.9(2) . . ? O1A C1A H1A1 110.1 . . ? C2 C1A H1A1 110.1 . . ? O1A C1A H1A2 110.1 . . ? C2 C1A H1A2 110.1 . . ? H1A1 C1A H1A2 108.4 . . ? C1A C2 C5 119.96(16) . . ? C1A C2 C4 108.16(14) . . ? C5 C2 C4 107.42(9) . . ? C1A C2 C3 105.67(14) . . ? C5 C2 C3 107.23(9) . . ? C4 C2 C3 107.90(10) . . ? C5 C2 C1 101.55(13) . . ? C4 C2 C1 114.60(12) . . ? C3 C2 C1 117.31(13) . . ? N1 C3 C2 111.08(9) . . ? N1 C3 H3A 109.4 . . ? C2 C3 H3A 109.4 . . ? N1 C3 H3B 109.4 . . ? C2 C3 H3B 109.4 . . ? H3A C3 H3B 108.0 . . ? N2 C4 C2 111.05(9) . . ? N2 C4 H4A 109.4 . . ? C2 C4 H4A 109.4 . . ? N2 C4 H4B 109.4 . . ? C2 C4 H4B 109.4 . . ? H4A C4 H4B 108.0 . . ? N3 C5 C2 111.25(9) . . ? N3 C5 H5A 109.4 . . ? C2 C5 H5A 109.4 . . ? N3 C5 H5B 109.4 . . ? C2 C5 H5B 109.4 . . ? H5A C5 H5B 108.0 . . ? N1 C6 N2 112.80(9) . . ? N1 C6 C7 113.52(9) . . ? N2 C6 C7 110.98(9) . . ? N1 C6 H6 106.3 . . ? N2 C6 H6 106.3 . . ? C7 C6 H6 106.3 . . ? N4 C7 C8 122.66(11) . . ? N4 C7 C6 117.45(11) . . ? C8 C7 C6 119.69(10) . . ? C9 C8 C7 118.74(12) . . ? C9 C8 H8 120.6 . . ? C7 C8 H8 120.6 . . ? N4 C11 C10 123.99(13) . . ? N4 C11 H11 118.0 . . ? C10 C11 H11 118.0 . . ? C11 C10 C9 118.22(12) . . ? C11 C10 H10 120.9 . . ? C9 C10 H10 120.9 . . ? C10 C9 C8 119.30(13) . . ? C10 C9 H9 120.3 . . ? C8 C9 H9 120.3 . . ? N3 C12 N2 112.91(9) . . ? N3 C12 C13 112.27(9) . . ? N2 C12 C13 112.06(9) . . ? N3 C12 H12 106.3 . . ? N2 C12 H12 106.3 . . ? C13 C12 H12 106.3 . . ? N5 C13 C14 122.52(11) . . ? N5 C13 C12 117.03(10) . . ? C14 C13 C12 120.26(11) . . ? C15 C14 C13 118.86(12) . . ? C15 C14 H14 120.6 . . ? C13 C14 H14 120.6 . . ? C16 C15 C14 118.99(12) . . ? C16 C15 H15 120.5 . . ? C14 C15 H15 120.5 . . ? C17 C16 C15 118.56(12) . . ? C17 C16 H16 120.7 . . ? C15 C16 H16 120.7 . . ? N5 C17 C16 123.56(13) . . ? N5 C17 H17 118.2 . . ? C16 C17 H17 118.2 . . ? N3 C18 N1 112.99(9) . . ? N3 C18 C19 112.70(9) . . ? N1 C18 C19 112.72(9) . . ? N3 C18 H18 105.9 . . ? N1 C18 H18 105.9 . . ? C19 C18 H18 105.9 . . ? N6 C19 C20 122.44(11) . . ? N6 C19 C18 116.99(10) . . ? C20 C19 C18 120.25(11) . . ? C21 C20 C19 119.04(12) . . ? C21 C20 H20 120.5 . . ? C19 C20 H20 120.5 . . ? C22 C21 C20 118.98(13) . . ? C22 C21 H21 120.5 . . ? C20 C21 H21 120.5 . . ? C21 C22 C23 118.50(12) . . ? C21 C22 H22 120.7 . . ? C23 C22 H22 120.7 . . ? N6 C23 C22 123.63(13) . . ? N6 C23 H23 118.2 . . ? C22 C23 H23 118.2 . . ? C3 N1 C6 109.51(9) . . ? C3 N1 C18 109.62(9) . . ? C6 N1 C18 105.79(9) . . ? C12 N2 C4 109.24(9) . . ? C12 N2 C6 106.62(8) . . ? C4 N2 C6 109.34(9) . . ? C12 N3 C18 106.43(8) . . ? C12 N3 C5 109.53(9) . . ? C18 N3 C5 109.42(8) . . ? C7 N4 C11 117.08(12) . . ? C13 N5 C17 117.51(11) . . ? C23 N6 C19 117.40(11) . . ? C1 O1 H1O 109.5 . . ? C1A O1A H2O 109.5 . . ? H3O O2 H4O 104.0(16) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1A C1A C2 C5 70.8(2) . . . . ? O1A C1A C2 C4 -52.8(2) . . . . ? O1A C1A C2 C3 -168.11(19) . . . . ? O1A C1A C2 C1 60.7(5) . . . . ? O1 C1 C2 C1A -12.9(4) . . . . ? O1 C1 C2 C5 176.05(15) . . . . ? O1 C1 C2 C4 60.6(2) . . . . ? O1 C1 C2 C3 -67.5(2) . . . . ? C1A C2 C3 N1 172.94(15) . . . . ? C5 C2 C3 N1 -58.01(12) . . . . ? C4 C2 C3 N1 57.43(12) . . . . ? C1 C2 C3 N1 -171.34(14) . . . . ? C1A C2 C4 N2 -171.38(15) . . . . ? C5 C2 C4 N2 57.79(12) . . . . ? C3 C2 C4 N2 -57.52(12) . . . . ? C1 C2 C4 N2 169.78(14) . . . . ? C1A C2 C5 N3 178.62(14) . . . . ? C4 C2 C5 N3 -57.47(11) . . . . ? C3 C2 C5 N3 58.28(12) . . . . ? C1 C2 C5 N3 -178.10(12) . . . . ? N1 C6 C7 N4 -28.38(15) . . . . ? N2 C6 C7 N4 -156.66(11) . . . . ? N1 C6 C7 C8 156.65(11) . . . . ? N2 C6 C7 C8 28.37(15) . . . . ? N4 C7 C8 C9 1.0(2) . . . . ? C6 C7 C8 C9 175.70(11) . . . . ? N4 C11 C10 C9 0.4(2) . . . . ? C11 C10 C9 C8 0.1(2) . . . . ? C7 C8 C9 C10 -0.7(2) . . . . ? N3 C12 C13 N5 21.74(14) . . . . ? N2 C12 C13 N5 150.05(10) . . . . ? N3 C12 C13 C14 -163.15(10) . . . . ? N2 C12 C13 C14 -34.84(14) . . . . ? N5 C13 C14 C15 -0.24(18) . . . . ? C12 C13 C14 C15 -175.07(10) . . . . ? C13 C14 C15 C16 0.23(19) . . . . ? C14 C15 C16 C17 -0.1(2) . . . . ? C15 C16 C17 N5 0.0(2) . . . . ? N3 C18 C19 N6 -22.79(14) . . . . ? N1 C18 C19 N6 -152.15(10) . . . . ? N3 C18 C19 C20 163.60(10) . . . . ? N1 C18 C19 C20 34.24(15) . . . . ? N6 C19 C20 C21 -0.75(19) . . . . ? C18 C19 C20 C21 172.49(11) . . . . ? C19 C20 C21 C22 0.9(2) . . . . ? C20 C21 C22 C23 -0.4(2) . . . . ? C21 C22 C23 N6 -0.4(2) . . . . ? C2 C3 N1 C6 -57.85(12) . . . . ? C2 C3 N1 C18 57.80(12) . . . . ? N2 C6 N1 C3 58.53(12) . . . . ? C7 C6 N1 C3 -68.81(12) . . . . ? N2 C6 N1 C18 -59.52(11) . . . . ? C7 C6 N1 C18 173.14(9) . . . . ? N3 C18 N1 C3 -57.76(12) . . . . ? C19 C18 N1 C3 71.44(11) . . . . ? N3 C18 N1 C6 60.23(11) . . . . ? C19 C18 N1 C6 -170.57(9) . . . . ? N3 C12 N2 C4 58.69(11) . . . . ? C13 C12 N2 C4 -69.29(11) . . . . ? N3 C12 N2 C6 -59.36(11) . . . . ? C13 C12 N2 C6 172.66(9) . . . . ? C2 C4 N2 C12 -58.34(12) . . . . ? C2 C4 N2 C6 57.99(12) . . . . ? N1 C6 N2 C12 59.43(11) . . . . ? C7 C6 N2 C12 -171.90(9) . . . . ? N1 C6 N2 C4 -58.55(12) . . . . ? C7 C6 N2 C4 70.12(12) . . . . ? N2 C12 N3 C18 59.77(11) . . . . ? C13 C12 N3 C18 -172.37(9) . . . . ? N2 C12 N3 C5 -58.42(11) . . . . ? C13 C12 N3 C5 69.44(11) . . . . ? N1 C18 N3 C12 -60.45(11) . . . . ? C19 C18 N3 C12 170.34(9) . . . . ? N1 C18 N3 C5 57.82(12) . . . . ? C19 C18 N3 C5 -71.40(11) . . . . ? C2 C5 N3 C12 57.91(11) . . . . ? C2 C5 N3 C18 -58.40(12) . . . . ? C8 C7 N4 C11 -0.6(2) . . . . ? C6 C7 N4 C11 -175.36(13) . . . . ? C10 C11 N4 C7 -0.1(2) . . . . ? C14 C13 N5 C17 0.14(17) . . . . ? C12 C13 N5 C17 175.13(10) . . . . ? C16 C17 N5 C13 -0.03(19) . . . . ? C22 C23 N6 C19 0.63(19) . . . . ? C20 C19 N6 C23 -0.03(18) . . . . ? C18 C19 N6 C23 -173.48(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 O1 H1O O2 0.84 2.11 2.8672(18) 150.1 . O1A H2O O2 0.84 1.93 2.733(2) 158.9 . O2 H3O N6 0.891(18) 2.052(19) 2.9421(15) 177.5(17) 2_666 O2 H4O N5 0.89(2) 2.02(2) 2.9139(16) 172.8(16) 2_666 O2 H4O N3 0.89(2) 2.544(18) 3.0221(14) 114.1(13) 2_666 _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 29.97 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.408 _refine_diff_density_min -0.245 _refine_diff_density_rms 0.049 data_5 _database_code_depnum_ccdc_archive 'CCDC 845925' #TrackingRef 'combined_final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H25 N6 O1.50' _chemical_formula_weight 409.49 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.9607(14) _cell_length_b 10.8190(13) _cell_length_c 18.360(2) _cell_angle_alpha 82.815(7) _cell_angle_beta 83.582(7) _cell_angle_gamma 83.467(6) _cell_volume 1940.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 49248 _cell_measurement_theta_min 2.07 _cell_measurement_theta_max 25.68 _exptl_crystal_description platelet _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.402 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 868 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type none _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 (346 frames)' _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 49248 _diffrn_reflns_av_R_equivalents 0.0757 _diffrn_reflns_av_sigmaI/netI 0.1149 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 25.68 _reflns_number_total 7359 _reflns_number_gt 4098 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 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 O 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 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^)+(0.0493P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7359 _refine_ls_number_parameters 550 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1171 _refine_ls_R_factor_gt 0.0516 _refine_ls_wR_factor_ref 0.1232 _refine_ls_wR_factor_gt 0.1036 _refine_ls_goodness_of_fit_ref 0.930 _refine_ls_restrained_S_all 0.930 _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 0.198 _refine_diff_density_min -0.308 _refine_diff_density_rms 0.054 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 O1A O 0.82641(18) -0.15883(15) 0.28030(9) 0.0261(4) Uani 1 1 d . . . H1A H 0.9173 -0.1589 0.2925 0.031 Uiso 1 1 d R . . N1A N 0.6260(2) 0.19323(19) 0.11529(10) 0.0208(5) Uani 1 1 d . . . N2A N 0.8080(2) 0.04649(18) 0.06075(10) 0.0200(5) Uani 1 1 d . . . N3A N 0.5798(2) -0.02125(18) 0.10041(10) 0.0198(5) Uani 1 1 d . . . N4A N 0.6198(2) 0.4217(2) -0.08765(11) 0.0264(5) Uani 1 1 d . . . N5A N 0.9274(2) -0.3008(2) -0.02581(12) 0.0290(6) Uani 1 1 d . . . N6A N 0.1874(2) 0.0508(2) 0.20295(11) 0.0246(5) Uani 1 1 d . . . C1A C 0.7506(3) 0.1788(2) 0.06294(13) 0.0212(6) Uani 1 1 d . . . H1E H 0.8191 0.2212 0.0818 0.025 Uiso 1 1 calc R . . C2A C 0.6995(3) -0.0267(2) 0.04495(13) 0.0205(6) Uani 1 1 d . . . H2A H 0.6676 0.0137 -0.0017 0.025 Uiso 1 1 calc R . . C3A C 0.5268(2) 0.1124(2) 0.09693(13) 0.0206(6) Uani 1 1 d . . . H3A H 0.5117 0.1391 0.0452 0.025 Uiso 1 1 calc R . . C4A C 0.6670(3) 0.1496(2) 0.19021(13) 0.0227(6) Uani 1 1 d . . . H4A H 0.5883 0.1574 0.2262 0.027 Uiso 1 1 calc R . . H4B H 0.7329 0.2018 0.2018 0.027 Uiso 1 1 calc R . . C5A C 0.8509(3) 0.0007(2) 0.13530(13) 0.0222(6) Uani 1 1 d . . . H5A H 0.9212 0.0492 0.1457 0.027 Uiso 1 1 calc R . . H5B H 0.8885 -0.0862 0.1364 0.027 Uiso 1 1 calc R . . C6A C 0.6235(3) -0.0664(2) 0.17522(12) 0.0206(6) Uani 1 1 d . . . H6A H 0.6614 -0.1532 0.1763 0.025 Uiso 1 1 calc R . . H6B H 0.5450 -0.0622 0.2116 0.025 Uiso 1 1 calc R . . C7A C 0.7292(3) 0.0122(2) 0.19508(13) 0.0212(6) Uani 1 1 d . . . C8A C 0.7709(3) -0.0304(2) 0.27236(13) 0.0245(6) Uani 1 1 d . . . H8A H 0.8378 0.0216 0.2829 0.029 Uiso 1 1 calc R . . H8B H 0.6922 -0.0194 0.3081 0.029 Uiso 1 1 calc R . . C9A C 0.7297(3) 0.2456(2) -0.01344(13) 0.0204(6) Uani 1 1 d . . . C10A C 0.6350(3) 0.3504(2) -0.02290(14) 0.0240(6) Uani 1 1 d . . . H10A H 0.5786 0.3725 0.0183 0.029 Uiso 1 1 calc R . . C11A C 0.7016(3) 0.3865(2) -0.14588(14) 0.0277(7) Uani 1 1 d . . . H11A H 0.6931 0.4339 -0.1913 0.033 Uiso 1 1 calc R . . C12A C 0.7979(3) 0.2842(3) -0.14289(14) 0.0290(7) Uani 1 1 d . . . H12A H 0.8522 0.2638 -0.1851 0.035 Uiso 1 1 calc R . . C13A C 0.8120(3) 0.2124(2) -0.07546(14) 0.0265(6) Uani 1 1 d . . . H13A H 0.8760 0.1428 -0.0719 0.032 Uiso 1 1 calc R . . C14A C 0.7526(3) -0.1602(2) 0.03164(13) 0.0199(6) Uani 1 1 d . . . C15A C 0.8786(3) -0.1868(2) -0.00677(14) 0.0255(6) Uani 1 1 d . . . H15A H 0.9329 -0.1216 -0.0203 0.031 Uiso 1 1 calc R . . C16A C 0.8479(3) -0.3935(3) -0.00509(14) 0.0277(7) Uani 1 1 d . . . H16A H 0.8795 -0.4732 -0.0174 0.033 Uiso 1 1 calc R . . C17A C 0.7210(3) -0.3765(2) 0.03374(14) 0.0259(6) Uani 1 1 d . . . H17A H 0.6693 -0.4435 0.0475 0.031 Uiso 1 1 calc R . . C18A C 0.6728(3) -0.2586(2) 0.05168(13) 0.0247(6) Uani 1 1 d . . . H18A H 0.5873 -0.2449 0.0771 0.030 Uiso 1 1 calc R . . C19A C 0.3902(3) 0.1342(2) 0.14086(13) 0.0201(6) Uani 1 1 d . . . C20A C 0.3118(3) 0.0359(2) 0.16600(13) 0.0228(6) Uani 1 1 d . . . H20A H 0.3473 -0.0446 0.1568 0.027 Uiso 1 1 calc R . . C21A C 0.1360(3) 0.1682(2) 0.21355(14) 0.0267(6) Uani 1 1 d . . . H21A H 0.0499 0.1805 0.2386 0.032 Uiso 1 1 calc R . . C22A C 0.2054(3) 0.2717(2) 0.18881(14) 0.0262(6) Uani 1 1 d . . . H22A H 0.1659 0.3517 0.1964 0.031 Uiso 1 1 calc R . . C23A C 0.3347(3) 0.2543(2) 0.15267(13) 0.0235(6) Uani 1 1 d . . . H23A H 0.3838 0.3225 0.1365 0.028 Uiso 1 1 calc R . . O1B O 0.09226(17) 0.85433(16) 0.29683(9) 0.0240(4) Uani 1 1 d . . . H1B H 0.1161 0.9132 0.2579 0.029 Uiso 1 1 d R . . N1B N 0.4770(2) 0.79398(18) 0.39804(10) 0.0204(5) Uani 1 1 d . . . N2B N 0.3410(2) 0.80879(19) 0.51943(11) 0.0207(5) Uani 1 1 d . . . N3B N 0.3425(2) 0.62184(19) 0.45406(10) 0.0193(5) Uani 1 1 d . . . N4B N 0.8388(2) 0.7715(2) 0.49852(12) 0.0281(5) Uani 1 1 d . . . N5B N 0.0986(2) 0.6345(2) 0.70075(11) 0.0306(6) Uani 1 1 d . . . N6B N 0.4784(2) 0.42100(19) 0.27353(11) 0.0252(5) Uani 1 1 d . . . C1B C 0.4640(3) 0.8427(2) 0.47076(13) 0.0209(6) Uani 1 1 d . . . H1F H 0.4533 0.9342 0.4604 0.025 Uiso 1 1 calc R . . C2B C 0.3406(3) 0.6700(2) 0.52621(13) 0.0208(6) Uani 1 1 d . . . H2B H 0.4263 0.6351 0.5457 0.025 Uiso 1 1 calc R . . C3B C 0.4700(3) 0.6563(2) 0.41132(13) 0.0202(6) Uani 1 1 d . . . H3B H 0.5425 0.6235 0.4426 0.024 Uiso 1 1 calc R . . C4B C 0.3586(2) 0.8536(2) 0.35941(13) 0.0204(6) Uani 1 1 d . . . H4C H 0.3625 0.8228 0.3118 0.025 Uiso 1 1 calc R . . H4D H 0.3628 0.9435 0.3511 0.025 Uiso 1 1 calc R . . C5B C 0.2224(3) 0.8691(2) 0.48167(13) 0.0229(6) Uani 1 1 d . . . H5C H 0.2234 0.9593 0.4766 0.028 Uiso 1 1 calc R . . H5D H 0.1394 0.8484 0.5113 0.028 Uiso 1 1 calc R . . C6B C 0.2235(3) 0.6829(2) 0.41644(13) 0.0212(6) Uani 1 1 d . . . H6C H 0.1406 0.6616 0.4460 0.025 Uiso 1 1 calc R . . H6D H 0.2250 0.6515 0.3691 0.025 Uiso 1 1 calc R . . C7B C 0.2242(3) 0.8255(2) 0.40466(13) 0.0203(6) Uani 1 1 d . . . C8B C 0.1006(3) 0.8914(2) 0.36873(13) 0.0235(6) Uani 1 1 d . . . H8C H 0.0190 0.8725 0.4003 0.028 Uiso 1 1 calc R . . H8D H 0.1047 0.9812 0.3642 0.028 Uiso 1 1 calc R . . C9B C 0.5931(3) 0.8101(2) 0.50916(13) 0.0216(6) Uani 1 1 d . . . C10B C 0.7199(3) 0.7948(2) 0.46885(14) 0.0240(6) Uani 1 1 d . . . H10B H 0.7223 0.8012 0.4177 0.029 Uiso 1 1 calc R . . C11B C 0.8319(3) 0.7633(2) 0.57270(15) 0.0282(7) Uani 1 1 d . . . H11B H 0.9126 0.7466 0.5948 0.034 Uiso 1 1 calc R . . C12B C 0.7122(3) 0.7782(2) 0.61768(14) 0.0276(6) Uani 1 1 d . . . H12B H 0.7129 0.7723 0.6686 0.033 Uiso 1 1 calc R . . C13B C 0.5904(3) 0.8022(2) 0.58579(14) 0.0248(6) Uani 1 1 d . . . H13B H 0.5084 0.8127 0.6150 0.030 Uiso 1 1 calc R . . C14B C 0.2292(3) 0.6224(2) 0.58195(13) 0.0219(6) Uani 1 1 d . . . C15B C 0.1876(3) 0.6790(3) 0.64596(13) 0.0254(6) Uani 1 1 d . . . H15B H 0.2238 0.7527 0.6511 0.031 Uiso 1 1 calc R . . C16B C 0.0488(3) 0.5276(3) 0.69234(14) 0.0307(7) Uani 1 1 d . . . H16B H -0.0117 0.4943 0.7300 0.037 Uiso 1 1 calc R . . C17B C 0.0822(3) 0.4642(3) 0.63113(14) 0.0283(7) Uani 1 1 d . . . H17B H 0.0444 0.3907 0.6276 0.034 Uiso 1 1 calc R . . C18B C 0.1735(3) 0.5126(2) 0.57489(14) 0.0247(6) Uani 1 1 d . . . H18B H 0.1972 0.4719 0.5329 0.030 Uiso 1 1 calc R . . C19B C 0.5034(3) 0.5941(2) 0.34146(13) 0.0195(6) Uani 1 1 d . . . C20B C 0.4435(3) 0.4890(2) 0.33085(13) 0.0227(6) Uani 1 1 d . . . H20B H 0.3742 0.4634 0.3658 0.027 Uiso 1 1 calc R . . C21B C 0.5784(3) 0.4610(2) 0.22371(14) 0.0252(6) Uani 1 1 d . . . H21B H 0.6037 0.4172 0.1831 0.030 Uiso 1 1 calc R . . C22B C 0.6457(3) 0.5644(2) 0.22971(13) 0.0237(6) Uani 1 1 d . . . H22B H 0.7153 0.5880 0.1943 0.028 Uiso 1 1 calc R . . C23B C 0.6074(3) 0.6314(2) 0.28922(13) 0.0227(6) Uani 1 1 d . . . H23B H 0.6509 0.7011 0.2943 0.027 Uiso 1 1 calc R . . O1 O 1.1204(3) -0.4000(3) -0.13901(18) 0.0468(10) Uani 1 1 d . . . H1C H 1.0601 -0.3593 -0.1049 0.056 Uiso 1 1 d R . . H1D H 1.1061 -0.3765 -0.1905 0.056 Uiso 1 1 d 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 O1A 0.0236(10) 0.0223(10) 0.0329(10) 0.0010(8) -0.0101(8) -0.0017(8) N1A 0.0200(12) 0.0244(12) 0.0183(11) -0.0006(9) -0.0037(9) -0.0039(9) N2A 0.0199(12) 0.0197(11) 0.0208(11) -0.0012(9) -0.0055(9) -0.0012(9) N3A 0.0188(12) 0.0211(12) 0.0185(11) -0.0018(9) -0.0009(9) 0.0006(9) N4A 0.0281(13) 0.0243(12) 0.0267(12) 0.0004(10) -0.0037(11) -0.0051(10) N5A 0.0288(14) 0.0271(13) 0.0298(13) -0.0039(10) -0.0018(11) 0.0019(11) N6A 0.0196(12) 0.0299(13) 0.0234(11) -0.0005(10) -0.0002(10) -0.0030(10) C1A 0.0197(14) 0.0218(14) 0.0222(13) -0.0013(11) -0.0044(11) -0.0018(11) C2A 0.0180(14) 0.0228(14) 0.0210(13) -0.0010(11) -0.0020(11) -0.0043(11) C3A 0.0185(14) 0.0197(13) 0.0229(13) -0.0006(11) -0.0024(11) -0.0009(11) C4A 0.0229(15) 0.0244(14) 0.0208(13) -0.0036(11) -0.0033(11) -0.0007(12) C5A 0.0179(14) 0.0262(15) 0.0228(13) -0.0016(11) -0.0064(11) -0.0015(12) C6A 0.0218(14) 0.0205(14) 0.0193(13) -0.0019(11) -0.0031(11) -0.0008(11) C7A 0.0218(15) 0.0218(14) 0.0202(13) -0.0023(11) -0.0042(11) -0.0009(11) C8A 0.0243(15) 0.0239(15) 0.0255(14) -0.0006(12) -0.0064(12) -0.0018(12) C9A 0.0203(14) 0.0190(14) 0.0221(13) 0.0006(11) -0.0032(11) -0.0055(11) C10A 0.0249(15) 0.0225(14) 0.0249(14) -0.0010(12) -0.0020(12) -0.0054(12) C11A 0.0314(17) 0.0284(15) 0.0223(14) 0.0018(12) -0.0036(13) -0.0027(13) C12A 0.0311(17) 0.0331(16) 0.0214(14) -0.0029(12) 0.0022(12) -0.0028(13) C13A 0.0274(16) 0.0227(15) 0.0294(15) -0.0032(12) -0.0023(13) -0.0032(12) C14A 0.0215(14) 0.0203(14) 0.0179(12) -0.0022(10) -0.0030(11) -0.0002(11) C15A 0.0215(15) 0.0266(15) 0.0286(14) -0.0030(12) -0.0043(12) -0.0024(12) C16A 0.0327(17) 0.0239(15) 0.0264(14) -0.0054(12) -0.0060(13) 0.0037(13) C17A 0.0267(16) 0.0235(15) 0.0285(14) -0.0037(12) -0.0051(13) -0.0038(12) C18A 0.0259(15) 0.0265(15) 0.0217(13) -0.0027(11) -0.0040(12) -0.0011(12) C19A 0.0168(14) 0.0239(14) 0.0195(13) -0.0003(11) -0.0036(11) -0.0021(11) C20A 0.0201(15) 0.0253(15) 0.0227(13) -0.0040(11) -0.0015(12) 0.0000(12) C21A 0.0232(15) 0.0315(16) 0.0250(14) -0.0046(12) -0.0031(12) 0.0016(13) C22A 0.0266(16) 0.0224(15) 0.0291(15) -0.0046(12) -0.0037(13) 0.0030(12) C23A 0.0229(15) 0.0225(15) 0.0247(14) -0.0008(11) -0.0032(12) -0.0023(12) O1B 0.0261(10) 0.0251(10) 0.0208(9) -0.0003(8) -0.0059(8) -0.0025(8) N1B 0.0246(12) 0.0165(11) 0.0208(11) -0.0017(9) -0.0070(10) -0.0014(9) N2B 0.0201(12) 0.0198(11) 0.0218(11) 0.0010(9) -0.0051(9) -0.0014(9) N3B 0.0163(11) 0.0225(12) 0.0188(11) -0.0016(9) -0.0018(9) -0.0013(9) N4B 0.0245(13) 0.0276(13) 0.0327(13) 0.0002(10) -0.0073(10) -0.0049(10) N5B 0.0287(14) 0.0361(14) 0.0240(12) -0.0022(11) 0.0004(10) 0.0044(11) N6B 0.0288(14) 0.0216(12) 0.0260(12) -0.0054(10) -0.0062(10) 0.0003(10) C1B 0.0223(15) 0.0185(14) 0.0218(13) -0.0032(11) -0.0028(11) -0.0007(11) C2B 0.0238(15) 0.0184(14) 0.0203(13) -0.0021(11) -0.0033(11) -0.0017(11) C3B 0.0198(14) 0.0178(13) 0.0225(13) 0.0000(11) -0.0032(11) -0.0016(11) C4B 0.0203(14) 0.0190(14) 0.0215(13) -0.0001(11) -0.0035(11) -0.0011(11) C5B 0.0230(15) 0.0217(14) 0.0232(13) 0.0001(11) -0.0048(12) 0.0010(12) C6B 0.0190(14) 0.0226(14) 0.0221(13) -0.0025(11) -0.0024(11) -0.0016(11) C7B 0.0207(14) 0.0216(14) 0.0189(13) -0.0008(11) -0.0040(11) -0.0027(11) C8B 0.0242(15) 0.0237(14) 0.0218(13) -0.0010(11) -0.0034(12) -0.0003(12) C9B 0.0239(15) 0.0178(13) 0.0237(13) -0.0019(11) -0.0047(12) -0.0034(11) C10B 0.0239(15) 0.0232(14) 0.0258(14) -0.0022(11) -0.0052(12) -0.0037(12) C11B 0.0285(17) 0.0230(15) 0.0348(16) 0.0008(13) -0.0128(13) -0.0048(13) C12B 0.0323(17) 0.0281(15) 0.0242(14) -0.0001(12) -0.0109(13) -0.0060(13) C13B 0.0304(16) 0.0199(14) 0.0248(14) -0.0020(11) -0.0028(12) -0.0060(12) C14B 0.0199(14) 0.0212(14) 0.0232(13) 0.0001(11) -0.0027(11) 0.0013(11) C15B 0.0253(15) 0.0267(15) 0.0234(14) -0.0022(12) -0.0047(12) 0.0026(12) C16B 0.0252(16) 0.0358(17) 0.0272(15) 0.0052(13) 0.0011(12) 0.0001(14) C17B 0.0231(15) 0.0302(16) 0.0299(15) 0.0043(13) -0.0024(12) -0.0046(12) C18B 0.0222(15) 0.0261(15) 0.0243(14) 0.0013(12) -0.0034(12) 0.0004(12) C19B 0.0205(14) 0.0171(13) 0.0214(13) -0.0026(11) -0.0051(11) -0.0001(11) C20B 0.0221(15) 0.0250(15) 0.0206(13) -0.0017(11) -0.0030(11) -0.0014(12) C21B 0.0297(16) 0.0235(15) 0.0214(14) -0.0022(11) -0.0033(12) 0.0023(12) C22B 0.0231(15) 0.0242(15) 0.0220(13) 0.0014(12) -0.0028(11) 0.0011(12) C23B 0.0226(15) 0.0204(14) 0.0254(14) -0.0005(11) -0.0056(12) -0.0023(12) O1 0.045(2) 0.062(3) 0.0302(18) -0.0089(17) 0.0003(17) 0.0061(19) _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 O1A C8A 1.431(3) . ? O1A H1A 0.9561 . ? N1A C3A 1.483(3) . ? N1A C4A 1.484(3) . ? N1A C1A 1.488(3) . ? N2A C1A 1.484(3) . ? N2A C2A 1.484(3) . ? N2A C5A 1.488(3) . ? N3A C3A 1.478(3) . ? N3A C2A 1.480(3) . ? N3A C6A 1.494(3) . ? N4A C11A 1.338(3) . ? N4A C10A 1.348(3) . ? N5A C16A 1.340(3) . ? N5A C15A 1.346(3) . ? N6A C21A 1.343(3) . ? N6A C20A 1.348(3) . ? C1A C9A 1.520(3) . ? C1A H1E 0.9800 . ? C2A C14A 1.520(3) . ? C2A H2A 0.9800 . ? C3A C19A 1.512(3) . ? C3A H3A 0.9800 . ? C4A C7A 1.539(3) . ? C4A H4A 0.9700 . ? C4A H4B 0.9700 . ? C5A C7A 1.547(3) . ? C5A H5A 0.9700 . ? C5A H5B 0.9700 . ? C6A C7A 1.527(3) . ? C6A H6A 0.9700 . ? C6A H6B 0.9700 . ? C7A C8A 1.524(3) . ? C8A H8A 0.9700 . ? C8A H8B 0.9700 . ? C9A C13A 1.387(4) . ? C9A C10A 1.396(3) . ? C10A H10A 0.9300 . ? C11A C12A 1.378(4) . ? C11A H11A 0.9300 . ? C12A C13A 1.389(3) . ? C12A H12A 0.9300 . ? C13A H13A 0.9300 . ? C14A C15A 1.387(4) . ? C14A C18A 1.390(4) . ? C15A H15A 0.9300 . ? C16A C17A 1.385(4) . ? C16A H16A 0.9300 . ? C17A C18A 1.378(4) . ? C17A H17A 0.9300 . ? C18A H18A 0.9300 . ? C19A C23A 1.387(3) . ? C19A C20A 1.393(3) . ? C20A H20A 0.9300 . ? C21A C22A 1.385(4) . ? C21A H21A 0.9300 . ? C22A C23A 1.385(4) . ? C22A H22A 0.9300 . ? C23A H23A 0.9300 . ? O1B C8B 1.440(3) . ? O1B H1B 0.9243 . ? N1B C1B 1.483(3) . ? N1B C4B 1.486(3) . ? N1B C3B 1.487(3) . ? N2B C5B 1.482(3) . ? N2B C1B 1.486(3) . ? N2B C2B 1.492(3) . ? N3B C3B 1.477(3) . ? N3B C2B 1.480(3) . ? N3B C6B 1.486(3) . ? N4B C10B 1.344(3) . ? N4B C11B 1.348(3) . ? N5B C16B 1.342(4) . ? N5B C15B 1.344(3) . ? N6B C21B 1.346(3) . ? N6B C20B 1.350(3) . ? C1B C9B 1.520(3) . ? C1B H1F 0.9800 . ? C2B C14B 1.513(3) . ? C2B H2B 0.9800 . ? C3B C19B 1.509(3) . ? C3B H3B 0.9800 . ? C4B C7B 1.535(3) . ? C4B H4C 0.9700 . ? C4B H4D 0.9700 . ? C5B C7B 1.543(3) . ? C5B H5C 0.9700 . ? C5B H5D 0.9700 . ? C6B C7B 1.532(3) . ? C6B H6C 0.9700 . ? C6B H6D 0.9700 . ? C7B C8B 1.525(3) . ? C8B H8C 0.9700 . ? C8B H8D 0.9700 . ? C9B C10B 1.395(4) . ? C9B C13B 1.396(3) . ? C10B H10B 0.9300 . ? C11B C12B 1.378(4) . ? C11B H11B 0.9300 . ? C12B C13B 1.390(4) . ? C12B H12B 0.9300 . ? C13B H13B 0.9300 . ? C14B C18B 1.393(4) . ? C14B C15B 1.394(4) . ? C15B H15B 0.9300 . ? C16B C17B 1.378(4) . ? C16B H16B 0.9300 . ? C17B C18B 1.389(4) . ? C17B H17B 0.9300 . ? C18B H18B 0.9300 . ? C19B C20B 1.386(4) . ? C19B C23B 1.391(3) . ? C20B H20B 0.9300 . ? C21B C22B 1.390(4) . ? C21B H21B 0.9300 . ? C22B C23B 1.381(3) . ? C22B H22B 0.9300 . ? C23B H23B 0.9300 . ? O1 H1C 0.9342 . ? O1 H1D 0.9700 . ? 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 C8A O1A H1A 106.1 . . ? C3A N1A C4A 109.63(19) . . ? C3A N1A C1A 108.50(19) . . ? C4A N1A C1A 106.84(18) . . ? C1A N2A C2A 108.34(19) . . ? C1A N2A C5A 106.84(19) . . ? C2A N2A C5A 109.61(19) . . ? C3A N3A C2A 105.42(18) . . ? C3A N3A C6A 109.98(19) . . ? C2A N3A C6A 109.43(18) . . ? C11A N4A C10A 116.1(2) . . ? C16A N5A C15A 116.7(2) . . ? C21A N6A C20A 117.3(2) . . ? N2A C1A N1A 113.1(2) . . ? N2A C1A C9A 112.3(2) . . ? N1A C1A C9A 112.11(19) . . ? N2A C1A H1E 106.2 . . ? N1A C1A H1E 106.2 . . ? C9A C1A H1E 106.2 . . ? N3A C2A N2A 113.0(2) . . ? N3A C2A C14A 112.4(2) . . ? N2A C2A C14A 112.4(2) . . ? N3A C2A H2A 106.1 . . ? N2A C2A H2A 106.1 . . ? C14A C2A H2A 106.1 . . ? N3A C3A N1A 113.07(19) . . ? N3A C3A C19A 113.1(2) . . ? N1A C3A C19A 112.0(2) . . ? N3A C3A H3A 106.0 . . ? N1A C3A H3A 106.0 . . ? C19A C3A H3A 106.0 . . ? N1A C4A C7A 110.87(19) . . ? N1A C4A H4A 109.5 . . ? C7A C4A H4A 109.5 . . ? N1A C4A H4B 109.5 . . ? C7A C4A H4B 109.5 . . ? H4A C4A H4B 108.1 . . ? N2A C5A C7A 110.79(19) . . ? N2A C5A H5A 109.5 . . ? C7A C5A H5A 109.5 . . ? N2A C5A H5B 109.5 . . ? C7A C5A H5B 109.5 . . ? H5A C5A H5B 108.1 . . ? N3A C6A C7A 111.34(19) . . ? N3A C6A H6A 109.4 . . ? C7A C6A H6A 109.4 . . ? N3A C6A H6B 109.4 . . ? C7A C6A H6B 109.4 . . ? H6A C6A H6B 108.0 . . ? C8A C7A C6A 111.7(2) . . ? C8A C7A C4A 110.0(2) . . ? C6A C7A C4A 107.8(2) . . ? C8A C7A C5A 112.0(2) . . ? C6A C7A C5A 106.5(2) . . ? C4A C7A C5A 108.7(2) . . ? O1A C8A C7A 112.1(2) . . ? O1A C8A H8A 109.2 . . ? C7A C8A H8A 109.2 . . ? O1A C8A H8B 109.2 . . ? C7A C8A H8B 109.2 . . ? H8A C8A H8B 107.9 . . ? C13A C9A C10A 117.3(2) . . ? C13A C9A C1A 121.5(2) . . ? C10A C9A C1A 121.0(2) . . ? N4A C10A C9A 124.5(2) . . ? N4A C10A H10A 117.8 . . ? C9A C10A H10A 117.8 . . ? N4A C11A C12A 124.2(2) . . ? N4A C11A H11A 117.9 . . ? C12A C11A H11A 117.9 . . ? C11A C12A C13A 118.6(3) . . ? C11A C12A H12A 120.7 . . ? C13A C12A H12A 120.7 . . ? C9A C13A C12A 119.3(2) . . ? C9A C13A H13A 120.4 . . ? C12A C13A H13A 120.4 . . ? C15A C14A C18A 117.2(2) . . ? C15A C14A C2A 121.1(2) . . ? C18A C14A C2A 121.5(2) . . ? N5A C15A C14A 124.4(3) . . ? N5A C15A H15A 117.8 . . ? C14A C15A H15A 117.8 . . ? N5A C16A C17A 123.2(3) . . ? N5A C16A H16A 118.4 . . ? C17A C16A H16A 118.4 . . ? C18A C17A C16A 118.8(3) . . ? C18A C17A H17A 120.6 . . ? C16A C17A H17A 120.6 . . ? C17A C18A C14A 119.7(3) . . ? C17A C18A H18A 120.2 . . ? C14A C18A H18A 120.2 . . ? C23A C19A C20A 117.8(2) . . ? C23A C19A C3A 120.7(2) . . ? C20A C19A C3A 121.3(2) . . ? N6A C20A C19A 123.7(2) . . ? N6A C20A H20A 118.2 . . ? C19A C20A H20A 118.2 . . ? N6A C21A C22A 122.9(3) . . ? N6A C21A H21A 118.6 . . ? C22A C21A H21A 118.6 . . ? C21A C22A C23A 119.1(2) . . ? C21A C22A H22A 120.5 . . ? C23A C22A H22A 120.5 . . ? C22A C23A C19A 119.2(3) . . ? C22A C23A H23A 120.4 . . ? C19A C23A H23A 120.4 . . ? C8B O1B H1B 114.5 . . ? C1B N1B C4B 106.86(19) . . ? C1B N1B C3B 107.96(18) . . ? C4B N1B C3B 109.37(19) . . ? C5B N2B C1B 106.56(17) . . ? C5B N2B C2B 109.4(2) . . ? C1B N2B C2B 108.02(19) . . ? C3B N3B C2B 105.77(19) . . ? C3B N3B C6B 110.36(18) . . ? C2B N3B C6B 109.38(19) . . ? C10B N4B C11B 116.2(2) . . ? C16B N5B C15B 116.6(2) . . ? C21B N6B C20B 116.1(2) . . ? N1B C1B N2B 113.9(2) . . ? N1B C1B C9B 111.9(2) . . ? N2B C1B C9B 112.35(19) . . ? N1B C1B H1F 106.0 . . ? N2B C1B H1F 106.0 . . ? C9B C1B H1F 106.0 . . ? N3B C2B N2B 112.82(18) . . ? N3B C2B C14B 112.5(2) . . ? N2B C2B C14B 112.9(2) . . ? N3B C2B H2B 105.9 . . ? N2B C2B H2B 105.9 . . ? C14B C2B H2B 105.9 . . ? N3B C3B N1B 112.9(2) . . ? N3B C3B C19B 113.5(2) . . ? N1B C3B C19B 112.35(19) . . ? N3B C3B H3B 105.8 . . ? N1B C3B H3B 105.8 . . ? C19B C3B H3B 105.8 . . ? N1B C4B C7B 111.22(18) . . ? N1B C4B H4C 109.4 . . ? C7B C4B H4C 109.4 . . ? N1B C4B H4D 109.4 . . ? C7B C4B H4D 109.4 . . ? H4C C4B H4D 108.0 . . ? N2B C5B C7B 111.2(2) . . ? N2B C5B H5C 109.4 . . ? C7B C5B H5C 109.4 . . ? N2B C5B H5D 109.4 . . ? C7B C5B H5D 109.4 . . ? H5C C5B H5D 108.0 . . ? N3B C6B C7B 111.4(2) . . ? N3B C6B H6C 109.4 . . ? C7B C6B H6C 109.4 . . ? N3B C6B H6D 109.4 . . ? C7B C6B H6D 109.4 . . ? H6C C6B H6D 108.0 . . ? C8B C7B C6B 112.7(2) . . ? C8B C7B C4B 112.66(19) . . ? C6B C7B C4B 107.1(2) . . ? C8B C7B C5B 108.5(2) . . ? C6B C7B C5B 106.73(19) . . ? C4B C7B C5B 108.9(2) . . ? O1B C8B C7B 112.5(2) . . ? O1B C8B H8C 109.1 . . ? C7B C8B H8C 109.1 . . ? O1B C8B H8D 109.1 . . ? C7B C8B H8D 109.1 . . ? H8C C8B H8D 107.8 . . ? C10B C9B C13B 117.3(2) . . ? C10B C9B C1B 121.1(2) . . ? C13B C9B C1B 121.4(2) . . ? N4B C10B C9B 124.7(2) . . ? N4B C10B H10B 117.6 . . ? C9B C10B H10B 117.6 . . ? N4B C11B C12B 123.8(2) . . ? N4B C11B H11B 118.1 . . ? C12B C11B H11B 118.1 . . ? C11B C12B C13B 119.0(2) . . ? C11B C12B H12B 120.5 . . ? C13B C12B H12B 120.5 . . ? C12B C13B C9B 119.0(3) . . ? C12B C13B H13B 120.5 . . ? C9B C13B H13B 120.5 . . ? C18B C14B C15B 117.1(3) . . ? C18B C14B C2B 121.1(2) . . ? C15B C14B C2B 121.5(2) . . ? N5B C15B C14B 124.4(3) . . ? N5B C15B H15B 117.8 . . ? C14B C15B H15B 117.8 . . ? N5B C16B C17B 123.8(3) . . ? N5B C16B H16B 118.1 . . ? C17B C16B H16B 118.1 . . ? C16B C17B C18B 118.6(3) . . ? C16B C17B H17B 120.7 . . ? C18B C17B H17B 120.7 . . ? C17B C18B C14B 119.5(3) . . ? C17B C18B H18B 120.3 . . ? C14B C18B H18B 120.3 . . ? C20B C19B C23B 117.3(2) . . ? C20B C19B C3B 121.6(2) . . ? C23B C19B C3B 120.6(2) . . ? N6B C20B C19B 124.8(3) . . ? N6B C20B H20B 117.6 . . ? C19B C20B H20B 117.6 . . ? N6B C21B C22B 123.5(2) . . ? N6B C21B H21B 118.2 . . ? C22B C21B H21B 118.2 . . ? C23B C22B C21B 118.7(3) . . ? C23B C22B H22B 120.6 . . ? C21B C22B H22B 120.6 . . ? C22B C23B C19B 119.5(3) . . ? C22B C23B H23B 120.2 . . ? C19B C23B H23B 120.2 . . ? H1C O1 H1D 116.0 . . ? 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 O1A H1A O1B 0.96 1.78 2.720(2) 168.7 1_645 O1B H1B N6A 0.92 1.86 2.751(3) 162.1 1_565 O1 H1C N5A 0.93 1.97 2.892(4) 170.8 . O1 H1D N5B 0.97 1.99 2.948(4) 167.2 1_644 data_6 _database_code_depnum_ccdc_archive 'CCDC 845926' #TrackingRef 'combined_final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H24 N6 O' _chemical_formula_sum 'C23 H24 N6 O' _chemical_formula_weight 400.48 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c ' _symmetry_space_group_name_Hall ' -P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.4820(19) _cell_length_b 26.344(5) _cell_length_c 7.7390(15) _cell_angle_alpha 90.00 _cell_angle_beta 100.12(3) _cell_angle_gamma 90.00 _cell_volume 1903.1(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7383 _cell_measurement_theta_min 2.4 _cell_measurement_theta_max 30.4 _exptl_crystal_description irregular _exptl_crystal_colour white _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.398 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type NONE _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details 'crystal-to-detector distance 60 mm' _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.76999 _diffrn_radiation_type synchrotron _diffrn_radiation_source synchrotron _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'ADSC Quantum210' _diffrn_measurement_method 'two \f and two \w scans with 2\% steps' _diffrn_detector_area_resol_mean 0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 7383 _diffrn_reflns_av_R_equivalents 0.0834 _diffrn_reflns_av_sigmaI/netI 0.0788 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -34 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 30.38 _reflns_number_total 3946 _reflns_number_gt 3082 _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 ; 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^)+(0.1167P)^2^+0.6847P] 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 0.059(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3946 _refine_ls_number_parameters 283 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0880 _refine_ls_R_factor_gt 0.0735 _refine_ls_wR_factor_ref 0.2229 _refine_ls_wR_factor_gt 0.2023 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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 N1 N 0.26689(19) 0.37090(7) 0.0062(2) 0.0410(4) Uani 1 1 d . . . N2 N 0.40648(19) 0.39782(6) 0.2893(2) 0.0403(4) Uani 1 1 d . . . N3 N 0.15648(18) 0.42717(6) 0.1970(2) 0.0379(4) Uani 1 1 d . . . N4 N -0.1115(3) 0.36269(11) -0.3522(3) 0.0731(7) Uani 1 1 d . . . N5 N 0.7613(2) 0.31421(9) 0.1650(4) 0.0690(7) Uani 1 1 d . . . N6 N 0.4307(2) 0.48039(8) 0.7590(3) 0.0544(5) Uani 1 1 d . . . C1 C 0.1683(2) 0.41375(8) 0.0144(3) 0.0404(5) Uani 1 1 d . . . H1 H 0.2103 0.4432 -0.0348 0.048 Uiso 1 1 calc R . . C2 C 0.4089(2) 0.38606(8) 0.1024(3) 0.0413(5) Uani 1 1 d . . . H2 H 0.4331 0.4179 0.0488 0.050 Uiso 1 1 calc R . . C3 C 0.3032(2) 0.44026(8) 0.2868(3) 0.0398(5) Uani 1 1 d . . . H3 H 0.3366 0.4671 0.2162 0.048 Uiso 1 1 calc R . . C4 C 0.2049(2) 0.33716(8) 0.2839(3) 0.0395(5) Uani 1 1 d . . . C5 C 0.3553(2) 0.35314(8) 0.3761(3) 0.0412(5) Uani 1 1 d . A . H5A H 0.3529 0.3612 0.4979 0.049 Uiso 1 1 calc R . . H5B H 0.4214 0.3251 0.3738 0.049 Uiso 1 1 calc R . . C6 C 0.2157(2) 0.32597(8) 0.0921(3) 0.0408(5) Uani 1 1 d . A . H6A H 0.2813 0.2979 0.0879 0.049 Uiso 1 1 calc R . . H6B H 0.1224 0.3160 0.0287 0.049 Uiso 1 1 calc R . . C7 C 0.1044(2) 0.38271(7) 0.2854(3) 0.0381(5) Uani 1 1 d . A . H7A H 0.0090 0.3737 0.2259 0.046 Uiso 1 1 calc R . . H7B H 0.0988 0.3915 0.4057 0.046 Uiso 1 1 calc R . . C8 C 0.0236(2) 0.40471(8) -0.0999(3) 0.0429(5) Uani 1 1 d . . . C9 C 0.0119(3) 0.37304(10) -0.2458(3) 0.0536(6) Uani 1 1 d . . . H9 H 0.0950 0.3582 -0.2706 0.064 Uiso 1 1 calc R . . C10 C -0.2298(3) 0.38531(12) -0.3108(4) 0.0703(9) Uani 1 1 d . . . H10 H -0.3178 0.3779 -0.3799 0.084 Uiso 1 1 calc R . . C11 C -0.2281(3) 0.41865(10) -0.1728(4) 0.0556(6) Uani 1 1 d . . . H11 H -0.3114 0.4341 -0.1513 0.067 Uiso 1 1 calc R . . C12 C -0.0996(3) 0.42785(9) -0.0702(3) 0.0469(5) Uani 1 1 d . . . H12 H -0.0947 0.4505 0.0230 0.056 Uiso 1 1 calc R . . C13 C 0.5236(2) 0.34811(9) 0.0756(3) 0.0470(5) Uani 1 1 d . . . C14 C 0.5066(3) 0.31802(11) -0.0742(4) 0.0578(6) Uani 1 1 d . . . H14 H 0.4219 0.3192 -0.1557 0.069 Uiso 1 1 calc R . . C15 C 0.6164(3) 0.28638(11) -0.1005(5) 0.0701(8) Uani 1 1 d . . . H15 H 0.6062 0.2658 -0.1995 0.084 Uiso 1 1 calc R . . C16 C 0.7404(3) 0.28551(11) 0.0197(6) 0.0756(10) Uani 1 1 d . . . H16 H 0.8137 0.2640 -0.0001 0.091 Uiso 1 1 calc R . . C17 C 0.6542(3) 0.34489(9) 0.1899(4) 0.0544(6) Uani 1 1 d . . . H17 H 0.6678 0.3653 0.2895 0.065 Uiso 1 1 calc R . . C18 C 0.3036(2) 0.46319(7) 0.4668(3) 0.0408(5) Uani 1 1 d . . . C19 C 0.4191(3) 0.45727(9) 0.6033(3) 0.0483(6) Uani 1 1 d . . . H19 H 0.4931 0.4358 0.5851 0.058 Uiso 1 1 calc R . . C20 C 0.3245(3) 0.51191(9) 0.7802(3) 0.0525(6) Uani 1 1 d . . . H20 H 0.3312 0.5289 0.8867 0.063 Uiso 1 1 calc R . . C21 C 0.2061(3) 0.52061(9) 0.6536(3) 0.0520(6) Uani 1 1 d . . . H21 H 0.1348 0.5429 0.6742 0.062 Uiso 1 1 calc R . . C22 C 0.1953(3) 0.49560(8) 0.4950(3) 0.0455(5) Uani 1 1 d . . . H22 H 0.1156 0.5005 0.4077 0.055 Uiso 1 1 calc R . . C23 C 0.1528(3) 0.29051(8) 0.3689(3) 0.0470(5) Uani 0.50 1 d P A 1 H23A H 0.2293 0.2656 0.3881 0.056 Uiso 0.50 1 calc PR A 1 H23B H 0.1313 0.2999 0.4827 0.056 Uiso 0.50 1 calc PR A 1 C23A C 0.1528(3) 0.29051(8) 0.3689(3) 0.0470(5) Uani 0.50 1 d P A 2 H23C H 0.0545 0.2836 0.3145 0.056 Uiso 0.50 1 calc PR A 2 H23D H 0.2104 0.2616 0.3470 0.056 Uiso 0.50 1 calc PR A 2 O1 O 0.0334(3) 0.26868(11) 0.2712(5) 0.0490(8) Uani 0.50 1 d P A 1 H1A H -0.0321 0.2894 0.2553 0.073 Uiso 0.50 1 calc PR A 1 O2 O 0.1596(6) 0.29575(13) 0.5514(5) 0.0760(14) Uani 0.50 1 d P A 2 H2A H 0.0901 0.2818 0.5804 0.114 Uiso 0.50 1 calc PR A 2 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 N1 0.0382(10) 0.0498(10) 0.0365(9) 0.0001(7) 0.0112(7) -0.0026(7) N2 0.0406(10) 0.0433(9) 0.0376(9) 0.0038(7) 0.0086(7) -0.0040(7) N3 0.0382(10) 0.0431(9) 0.0335(9) 0.0008(6) 0.0088(7) -0.0053(6) N4 0.0771(18) 0.0839(17) 0.0521(14) -0.0028(12) -0.0056(12) -0.0044(13) N5 0.0447(13) 0.0602(13) 0.105(2) 0.0188(13) 0.0214(12) 0.0035(9) N6 0.0635(13) 0.0546(11) 0.0418(11) 0.0013(8) 0.0004(9) -0.0163(9) C1 0.0403(12) 0.0495(11) 0.0323(10) 0.0034(8) 0.0089(8) -0.0041(8) C2 0.0387(12) 0.0486(11) 0.0381(11) 0.0033(8) 0.0109(8) -0.0049(8) C3 0.0381(11) 0.0434(10) 0.0381(11) 0.0020(8) 0.0077(8) -0.0046(8) C4 0.0434(12) 0.0410(10) 0.0365(10) -0.0010(7) 0.0136(8) -0.0043(8) C5 0.0457(12) 0.0420(10) 0.0370(10) 0.0026(8) 0.0105(8) -0.0030(8) C6 0.0401(12) 0.0466(11) 0.0379(11) -0.0046(8) 0.0127(8) -0.0032(8) C7 0.0405(11) 0.0413(10) 0.0341(10) 0.0001(7) 0.0105(8) -0.0059(8) C8 0.0464(12) 0.0512(12) 0.0315(10) 0.0044(8) 0.0081(8) -0.0020(9) C9 0.0492(14) 0.0729(16) 0.0384(12) -0.0067(10) 0.0072(9) 0.0039(11) C10 0.0598(18) 0.0781(19) 0.0627(18) 0.0173(14) -0.0175(13) -0.0160(14) C11 0.0406(14) 0.0689(16) 0.0541(15) 0.0153(11) -0.0008(10) 0.0026(10) C12 0.0503(14) 0.0532(12) 0.0364(11) 0.0022(9) 0.0055(9) 0.0010(9) C13 0.0433(13) 0.0521(12) 0.0492(13) 0.0052(9) 0.0182(9) -0.0042(9) C14 0.0538(15) 0.0702(16) 0.0549(15) -0.0012(11) 0.0242(11) 0.0036(11) C15 0.068(2) 0.0713(18) 0.080(2) -0.0045(15) 0.0391(16) 0.0034(13) C16 0.0594(19) 0.0628(17) 0.115(3) 0.0074(17) 0.0435(18) 0.0061(13) C17 0.0425(14) 0.0525(13) 0.0686(16) 0.0094(11) 0.0110(11) -0.0046(9) C18 0.0438(12) 0.0397(10) 0.0389(11) 0.0008(8) 0.0071(8) -0.0096(8) C19 0.0493(14) 0.0504(12) 0.0429(12) 0.0010(9) 0.0014(9) -0.0072(9) C20 0.0688(16) 0.0482(12) 0.0410(12) -0.0039(9) 0.0110(10) -0.0196(11) C21 0.0618(15) 0.0474(12) 0.0478(13) -0.0074(9) 0.0123(10) -0.0060(10) C22 0.0495(13) 0.0455(11) 0.0411(11) -0.0019(8) 0.0066(9) -0.0059(9) C23 0.0556(14) 0.0417(11) 0.0480(13) 0.0013(9) 0.0209(10) -0.0023(9) C23A 0.0556(14) 0.0417(11) 0.0480(13) 0.0013(9) 0.0209(10) -0.0023(9) O1 0.0485(19) 0.0353(15) 0.066(2) -0.0002(13) 0.0180(15) -0.0006(12) O2 0.146(4) 0.0377(17) 0.063(2) -0.0022(15) 0.069(3) -0.0066(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C2 1.474(3) . ? N1 C1 1.474(3) . ? N1 C6 1.481(3) . ? N2 C5 1.479(2) . ? N2 C2 1.484(3) . ? N2 C3 1.484(3) . ? N3 C1 1.480(3) . ? N3 C3 1.483(3) . ? N3 C7 1.484(2) . ? N4 C9 1.335(3) . ? N4 C10 1.357(4) . ? N5 C17 1.338(3) . ? N5 C16 1.340(5) . ? N6 C20 1.337(3) . ? N6 C19 1.338(3) . ? C1 C8 1.515(3) . ? C1 H1 0.9800 . ? C2 C13 1.518(3) . ? C2 H2 0.9800 . ? C3 C18 1.518(3) . ? C3 H3 0.9800 . ? C4 C23 1.517(3) . ? C4 C7 1.533(3) . ? C4 C6 1.534(3) . ? C4 C5 1.538(3) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C12 1.373(3) . ? C8 C9 1.392(3) . ? C9 H9 0.9300 . ? C10 C11 1.380(4) . ? C10 H10 0.9300 . ? C11 C12 1.354(3) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.390(4) . ? C13 C17 1.392(3) . ? C14 C15 1.377(4) . ? C14 H14 0.9300 . ? C15 C16 1.366(5) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 C22 1.382(3) . ? C18 C19 1.390(3) . ? C19 H19 0.9300 . ? C20 C21 1.373(4) . ? C20 H20 0.9300 . ? C21 C22 1.381(3) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C23 O1 1.372(4) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? O1 H1A 0.8200 . ? O2 H2A 0.8200 . ? 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 C2 N1 C1 107.49(16) . . ? C2 N1 C6 109.40(17) . . ? C1 N1 C6 109.42(16) . . ? C5 N2 C2 109.83(16) . . ? C5 N2 C3 109.73(16) . . ? C2 N2 C3 105.51(16) . . ? C1 N3 C3 106.29(16) . . ? C1 N3 C7 109.81(15) . . ? C3 N3 C7 109.19(16) . . ? C9 N4 C10 115.8(3) . . ? C17 N5 C16 117.2(3) . . ? C20 N6 C19 116.7(2) . . ? N1 C1 N3 112.28(16) . . ? N1 C1 C8 111.74(17) . . ? N3 C1 C8 112.49(17) . . ? N1 C1 H1 106.6 . . ? N3 C1 H1 106.6 . . ? C8 C1 H1 106.6 . . ? N1 C2 N2 112.31(16) . . ? N1 C2 C13 111.43(18) . . ? N2 C2 C13 113.87(18) . . ? N1 C2 H2 106.2 . . ? N2 C2 H2 106.2 . . ? C13 C2 H2 106.2 . . ? N3 C3 N2 113.17(16) . . ? N3 C3 C18 111.91(17) . . ? N2 C3 C18 113.11(17) . . ? N3 C3 H3 106.0 . . ? N2 C3 H3 106.0 . . ? C18 C3 H3 106.0 . . ? C23 C4 C7 112.37(17) . . ? C23 C4 C6 110.26(17) . . ? C7 C4 C6 107.79(17) . . ? C23 C4 C5 111.49(18) . . ? C7 C4 C5 108.00(16) . . ? C6 C4 C5 106.69(17) . . ? N2 C5 C4 111.02(17) . . ? N2 C5 H5A 109.4 . . ? C4 C5 H5A 109.4 . . ? N2 C5 H5B 109.4 . . ? C4 C5 H5B 109.4 . . ? H5A C5 H5B 108.0 . . ? N1 C6 C4 111.33(16) . . ? N1 C6 H6A 109.4 . . ? C4 C6 H6A 109.4 . . ? N1 C6 H6B 109.4 . . ? C4 C6 H6B 109.4 . . ? H6A C6 H6B 108.0 . . ? N3 C7 C4 110.89(16) . . ? N3 C7 H7A 109.5 . . ? C4 C7 H7A 109.5 . . ? N3 C7 H7B 109.5 . . ? C4 C7 H7B 109.5 . . ? H7A C7 H7B 108.1 . . ? C12 C8 C9 116.9(2) . . ? C12 C8 C1 122.9(2) . . ? C9 C8 C1 120.2(2) . . ? N4 C9 C8 124.0(2) . . ? N4 C9 H9 118.0 . . ? C8 C9 H9 118.0 . . ? N4 C10 C11 124.3(2) . . ? N4 C10 H10 117.8 . . ? C11 C10 H10 117.8 . . ? C12 C11 C10 117.1(3) . . ? C12 C11 H11 121.5 . . ? C10 C11 H11 121.5 . . ? C11 C12 C8 121.8(2) . . ? C11 C12 H12 119.1 . . ? C8 C12 H12 119.1 . . ? C14 C13 C17 117.0(2) . . ? C14 C13 C2 120.6(2) . . ? C17 C13 C2 122.2(2) . . ? C15 C14 C13 119.3(3) . . ? C15 C14 H14 120.4 . . ? C13 C14 H14 120.4 . . ? C16 C15 C14 119.5(3) . . ? C16 C15 H15 120.2 . . ? C14 C15 H15 120.2 . . ? N5 C16 C15 123.0(3) . . ? N5 C16 H16 118.5 . . ? C15 C16 H16 118.5 . . ? N5 C17 C13 123.9(3) . . ? N5 C17 H17 118.0 . . ? C13 C17 H17 118.0 . . ? C22 C18 C19 117.2(2) . . ? C22 C18 C3 120.59(19) . . ? C19 C18 C3 121.8(2) . . ? N6 C19 C18 124.2(2) . . ? N6 C19 H19 117.9 . . ? C18 C19 H19 117.9 . . ? N6 C20 C21 123.7(2) . . ? N6 C20 H20 118.2 . . ? C21 C20 H20 118.2 . . ? C20 C21 C22 118.6(2) . . ? C20 C21 H21 120.7 . . ? C22 C21 H21 120.7 . . ? C21 C22 C18 119.6(2) . . ? C21 C22 H22 120.2 . . ? C18 C22 H22 120.2 . . ? O1 C23 C4 113.6(2) . . ? O1 C23 H23A 108.8 . . ? C4 C23 H23A 108.8 . . ? O1 C23 H23B 108.8 . . ? C4 C23 H23B 108.8 . . ? H23A C23 H23B 107.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 N1 C1 N3 -59.7(2) . . . . ? C6 N1 C1 N3 59.0(2) . . . . ? C2 N1 C1 C8 172.81(16) . . . . ? C6 N1 C1 C8 -68.5(2) . . . . ? C3 N3 C1 N1 59.0(2) . . . . ? C7 N3 C1 N1 -59.0(2) . . . . ? C3 N3 C1 C8 -173.97(16) . . . . ? C7 N3 C1 C8 68.0(2) . . . . ? C1 N1 C2 N2 60.5(2) . . . . ? C6 N1 C2 N2 -58.2(2) . . . . ? C1 N1 C2 C13 -170.38(16) . . . . ? C6 N1 C2 C13 70.9(2) . . . . ? C5 N2 C2 N1 58.2(2) . . . . ? C3 N2 C2 N1 -60.0(2) . . . . ? C5 N2 C2 C13 -69.6(2) . . . . ? C3 N2 C2 C13 172.17(16) . . . . ? C1 N3 C3 N2 -60.2(2) . . . . ? C7 N3 C3 N2 58.2(2) . . . . ? C1 N3 C3 C18 170.54(16) . . . . ? C7 N3 C3 C18 -71.1(2) . . . . ? C5 N2 C3 N3 -57.8(2) . . . . ? C2 N2 C3 N3 60.5(2) . . . . ? C5 N2 C3 C18 70.8(2) . . . . ? C2 N2 C3 C18 -170.94(16) . . . . ? C2 N2 C5 C4 -58.4(2) . . . . ? C3 N2 C5 C4 57.1(2) . . . . ? C23 C4 C5 N2 178.53(17) . . . . ? C7 C4 C5 N2 -57.5(2) . . . . ? C6 C4 C5 N2 58.1(2) . . . . ? C2 N1 C6 C4 59.2(2) . . . . ? C1 N1 C6 C4 -58.4(2) . . . . ? C23 C4 C6 N1 -179.79(17) . . . . ? C7 C4 C6 N1 57.2(2) . . . . ? C5 C4 C6 N1 -58.6(2) . . . . ? C1 N3 C7 C4 57.9(2) . . . . ? C3 N3 C7 C4 -58.2(2) . . . . ? C23 C4 C7 N3 -178.47(17) . . . . ? C6 C4 C7 N3 -56.8(2) . . . . ? C5 C4 C7 N3 58.1(2) . . . . ? N1 C1 C8 C12 155.7(2) . . . . ? N3 C1 C8 C12 28.4(3) . . . . ? N1 C1 C8 C9 -26.4(3) . . . . ? N3 C1 C8 C9 -153.7(2) . . . . ? C10 N4 C9 C8 0.1(4) . . . . ? C12 C8 C9 N4 -2.7(4) . . . . ? C1 C8 C9 N4 179.3(2) . . . . ? C9 N4 C10 C11 2.3(4) . . . . ? N4 C10 C11 C12 -2.0(4) . . . . ? C10 C11 C12 C8 -0.8(4) . . . . ? C9 C8 C12 C11 2.9(3) . . . . ? C1 C8 C12 C11 -179.1(2) . . . . ? N1 C2 C13 C14 25.6(3) . . . . ? N2 C2 C13 C14 153.9(2) . . . . ? N1 C2 C13 C17 -160.1(2) . . . . ? N2 C2 C13 C17 -31.8(3) . . . . ? C17 C13 C14 C15 1.1(4) . . . . ? C2 C13 C14 C15 175.7(2) . . . . ? C13 C14 C15 C16 -0.7(4) . . . . ? C17 N5 C16 C15 -0.2(4) . . . . ? C14 C15 C16 N5 0.2(5) . . . . ? C16 N5 C17 C13 0.7(4) . . . . ? C14 C13 C17 N5 -1.2(4) . . . . ? C2 C13 C17 N5 -175.7(2) . . . . ? N3 C3 C18 C22 -37.4(3) . . . . ? N2 C3 C18 C22 -166.66(17) . . . . ? N3 C3 C18 C19 149.93(19) . . . . ? N2 C3 C18 C19 20.7(3) . . . . ? C20 N6 C19 C18 -1.6(3) . . . . ? C22 C18 C19 N6 0.7(3) . . . . ? C3 C18 C19 N6 173.6(2) . . . . ? C19 N6 C20 C21 1.2(3) . . . . ? N6 C20 C21 C22 -0.1(4) . . . . ? C20 C21 C22 C18 -0.8(3) . . . . ? C19 C18 C22 C21 0.5(3) . . . . ? C3 C18 C22 C21 -172.5(2) . . . . ? C7 C4 C23 O1 71.2(3) . . . . ? C6 C4 C23 O1 -49.1(3) . . . . ? C5 C4 C23 O1 -167.4(2) . . . . ? 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 O1 H1A N5 0.82 2.07 2.833(4) 155.4 1_455 _diffrn_measured_fraction_theta_max 0.932 _diffrn_reflns_theta_full 30.40 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 0.288 _refine_diff_density_min -0.309 _refine_diff_density_rms 0.057 data_7 _database_code_depnum_ccdc_archive 'CCDC 845927' #TrackingRef 'combined_final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H30 N6 O2' _chemical_formula_weight 446.55 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.0543(6) _cell_length_b 13.9730(12) _cell_length_c 15.4963(13) _cell_angle_alpha 78.685(4) _cell_angle_beta 84.184(4) _cell_angle_gamma 83.431(5) _cell_volume 2324.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 102280 _cell_measurement_theta_min 2.19 _cell_measurement_theta_max 25.68 _exptl_crystal_description platelet _exptl_crystal_colour colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.276 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 952 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type none _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 nine \w scans with 2\% steps (595 frames)' _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 102280 _diffrn_reflns_av_R_equivalents 0.0345 _diffrn_reflns_av_sigmaI/netI 0.0503 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 25.68 _reflns_number_total 8785 _reflns_number_gt 6077 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 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 atom O1 of molecule B is disordered over two positions which have been refined with occupancy parameters constrained to sum to unity. The diethylether solvent molecules are both disordered (the first one, containing O1, with the two positions sharing atom C1), and they have been affected with 0.5 occupancy parameters. All non-hydrogen atoms were refined with anisotropic displacement parameters, with some restraints on bond lengths and/or displacement parameters for the aoms of the solvent molecules. The H atom bound to O1A was found on a Fourier-difference map and all the others were introduced at calculated positions, except in the disordered parts. All were treated as riding atoms with an isotropic displacement parameter equal to 1.2 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^)+(0.1385P)^2^+0.6113P] 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 8785 _refine_ls_number_parameters 656 _refine_ls_number_restraints 39 _refine_ls_R_factor_all 0.0985 _refine_ls_R_factor_gt 0.0696 _refine_ls_wR_factor_ref 0.2196 _refine_ls_wR_factor_gt 0.2002 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.053 _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 1.457 _refine_diff_density_min -0.356 _refine_diff_density_rms 0.077 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 O1A O 0.09947(18) 0.73528(15) 0.78043(13) 0.0352(5) Uani 1 1 d . . . H1A H 0.1134 0.7665 0.8238 0.042 Uiso 1 1 d R . . N1A N 0.24112(18) 0.64874(15) 0.49421(14) 0.0229(5) Uani 1 1 d . . . N2A N 0.24070(18) 0.51756(16) 0.62743(13) 0.0230(5) Uani 1 1 d . . . N3A N 0.04611(18) 0.59649(15) 0.57076(13) 0.0210(5) Uani 1 1 d . . . N4A N 0.4190(2) 0.33872(17) 0.37942(15) 0.0302(5) Uani 1 1 d . . . N5A N -0.0874(2) 0.35080(19) 0.84279(16) 0.0381(6) Uani 1 1 d . . . N6A N -0.0894(2) 0.86186(19) 0.31553(17) 0.0396(6) Uani 1 1 d . . . C1A C 0.3055(2) 0.55754(18) 0.54196(16) 0.0225(5) Uani 1 1 d . . . H1B H 0.3827 0.5764 0.5564 0.027 Uiso 1 1 calc R . . C2A C 0.1136(2) 0.50450(18) 0.61169(16) 0.0226(5) Uani 1 1 d . . . H2A H 0.1203 0.4604 0.5691 0.027 Uiso 1 1 calc R . . C3A C 0.1142(2) 0.62866(18) 0.48488(16) 0.0219(5) Uani 1 1 d . . . H3A H 0.1216 0.5734 0.4537 0.026 Uiso 1 1 calc R . . C4A C 0.2379(2) 0.72441(18) 0.55024(16) 0.0237(5) Uani 1 1 d . . . H4A1 H 0.1952 0.7851 0.5217 0.028 Uiso 1 1 calc R . . H4A2 H 0.3207 0.7371 0.5566 0.028 Uiso 1 1 calc R . . C5A C 0.2374(2) 0.59162(19) 0.68485(16) 0.0250(6) Uani 1 1 d . . . H5A1 H 0.3202 0.6005 0.6951 0.030 Uiso 1 1 calc R . . H5A2 H 0.1945 0.5682 0.7415 0.030 Uiso 1 1 calc R . . C6A C 0.0438(2) 0.67136(19) 0.62737(17) 0.0241(5) Uani 1 1 d . . . H6A1 H 0.0001 0.6490 0.6839 0.029 Uiso 1 1 calc R . . H6A2 H 0.0004 0.7321 0.5996 0.029 Uiso 1 1 calc R . . C7A C 0.1733(2) 0.69036(19) 0.64210(16) 0.0248(6) Uani 1 1 d . . . C8A C 0.1699(2) 0.7668(2) 0.69947(18) 0.0299(6) Uani 1 1 d . . . H8A1 H 0.2523 0.7750 0.7113 0.036 Uiso 1 1 calc R . . H8A2 H 0.1335 0.8293 0.6694 0.036 Uiso 1 1 calc R . . C9A C 0.3404(2) 0.48089(19) 0.48455(16) 0.0239(5) Uani 1 1 d . . . C10A C 0.3613(2) 0.5071(2) 0.39315(17) 0.0267(6) Uani 1 1 d . . . H10A H 0.3498 0.5724 0.3655 0.032 Uiso 1 1 calc R . . C11A C 0.3992(2) 0.4347(2) 0.34389(18) 0.0295(6) Uani 1 1 d . . . H11A H 0.4118 0.4535 0.2829 0.035 Uiso 1 1 calc R . . C12A C 0.4007(2) 0.3147(2) 0.46761(19) 0.0304(6) Uani 1 1 d . . . H12A H 0.4142 0.2490 0.4938 0.037 Uiso 1 1 calc R . . C13A C 0.3627(2) 0.38209(19) 0.52207(17) 0.0256(6) Uani 1 1 d . . . H13A H 0.3522 0.3615 0.5829 0.031 Uiso 1 1 calc R . . C14A C 0.0437(2) 0.45398(19) 0.69426(17) 0.0244(5) Uani 1 1 d . . . C15A C 0.1005(3) 0.3773(2) 0.75231(19) 0.0340(7) Uani 1 1 d . . . H15A H 0.1836 0.3587 0.7428 0.041 Uiso 1 1 calc R . . C16A C 0.0330(3) 0.3291(2) 0.8240(2) 0.0410(8) Uani 1 1 d . . . H16A H 0.0733 0.2782 0.8618 0.049 Uiso 1 1 calc R . . C17A C -0.1411(2) 0.4243(2) 0.78613(18) 0.0304(6) Uani 1 1 d . . . H17A H -0.2242 0.4414 0.7971 0.037 Uiso 1 1 calc R . . C18A C -0.0809(2) 0.47674(19) 0.71227(17) 0.0255(6) Uani 1 1 d . . . H18A H -0.1235 0.5268 0.6750 0.031 Uiso 1 1 calc R . . C19A C 0.0441(2) 0.71337(18) 0.42782(17) 0.0243(5) Uani 1 1 d . . . C20A C -0.0810(2) 0.73522(19) 0.44455(17) 0.0263(6) Uani 1 1 d . . . H20A H -0.1228 0.7007 0.4939 0.032 Uiso 1 1 calc R . . C21A C -0.1425(2) 0.8084(2) 0.38742(19) 0.0318(6) Uani 1 1 d . . . H21A H -0.2263 0.8213 0.3996 0.038 Uiso 1 1 calc R . . C22A C 0.0313(3) 0.8401(2) 0.3001(2) 0.0390(7) Uani 1 1 d . . . H22A H 0.0709 0.8761 0.2506 0.047 Uiso 1 1 calc R . . C23A C 0.1005(2) 0.7675(2) 0.35311(18) 0.0314(6) Uani 1 1 d . . . H23A H 0.1838 0.7551 0.3388 0.038 Uiso 1 1 calc R . . O1B O 0.7468(4) 0.7539(3) 0.7040(3) 0.0422(14) Uani 0.479(6) 1 d P . . O1C O 0.7061(4) 0.6261(3) 0.8429(3) 0.0382(13) Uani 0.521(6) 1 d P . . N1B N 0.76847(19) 0.83810(15) 1.00117(14) 0.0246(5) Uani 1 1 d . . . N2B N 0.77115(18) 0.96557(15) 0.86462(14) 0.0234(5) Uani 1 1 d . . . N3B N 0.57829(18) 0.89668(15) 0.92768(14) 0.0239(5) Uani 1 1 d . . . N4B N 0.85815(19) 1.14392(16) 1.10659(14) 0.0259(5) Uani 1 1 d . . . N5B N 0.4496(2) 1.15026(18) 0.66019(16) 0.0345(6) Uani 1 1 d . . . N6B N 0.4413(2) 0.64344(18) 1.19221(16) 0.0364(6) Uani 1 1 d . . . C1B C 0.8253(2) 0.92562(18) 0.95016(16) 0.0236(5) Uani 1 1 d . . . H1C H 0.9105 0.9027 0.9348 0.028 Uiso 1 1 calc R . . C2B C 0.6374(2) 0.98515(18) 0.88341(17) 0.0229(5) Uani 1 1 d . . . H2B H 0.6262 1.0300 0.9255 0.028 Uiso 1 1 calc R . . C3B C 0.6346(2) 0.86443(19) 1.01247(16) 0.0240(5) Uani 1 1 d . . . H3B H 0.6231 0.9209 1.0422 0.029 Uiso 1 1 calc R . . C4B C 0.7937(2) 0.7601(2) 0.94682(18) 0.0298(6) Uani 1 1 d . . . H4B1 H 0.7573 0.7017 0.9777 0.036 Uiso 1 1 calc R . . H4B2 H 0.8813 0.7436 0.9387 0.036 Uiso 1 1 calc R . . C5B C 0.7965(2) 0.8888(2) 0.80958(18) 0.0278(6) Uani 1 1 d . . . H5B1 H 0.8841 0.8755 0.7980 0.033 Uiso 1 1 calc R . . H5B2 H 0.7616 0.9122 0.7534 0.033 Uiso 1 1 calc R . . C6B C 0.6034(2) 0.81962(19) 0.87290(18) 0.0274(6) Uani 1 1 d . . . H6B1 H 0.5680 0.8426 0.8169 0.033 Uiso 1 1 calc R . . H6B2 H 0.5657 0.7614 0.9027 0.033 Uiso 1 1 calc R . . C7B C 0.7421(2) 0.7937(2) 0.85620(18) 0.0291(6) Uani 1 1 d . . . C8B C 0.7698(3) 0.7140(2) 0.8002(2) 0.0392(7) Uani 1 1 d . . . C9B C 0.8305(2) 1.00268(19) 1.00516(16) 0.0231(5) Uani 1 1 d . . . C10B C 0.8397(2) 0.9770(2) 1.09630(17) 0.0264(6) Uani 1 1 d . . . H10B H 0.8367 0.9121 1.1248 0.032 Uiso 1 1 calc R . . C11B C 0.8534(2) 1.0485(2) 1.14357(17) 0.0266(6) Uani 1 1 d . . . H11B H 0.8596 1.0299 1.2041 0.032 Uiso 1 1 calc R . . C12B C 0.8507(2) 1.16845(19) 1.01877(17) 0.0246(5) Uani 1 1 d . . . H12B H 0.8546 1.2338 0.9918 0.030 Uiso 1 1 calc R . . C13B C 0.8374(2) 1.10128(19) 0.96688(17) 0.0252(6) Uani 1 1 d . . . H13B H 0.8331 1.1216 0.9063 0.030 Uiso 1 1 calc R . . C14B C 0.5746(2) 1.03870(19) 0.80239(17) 0.0247(6) Uani 1 1 d . . . C15B C 0.6297(2) 1.1088(2) 0.74025(18) 0.0301(6) Uani 1 1 d . . . H15B H 0.7100 1.1201 0.7446 0.036 Uiso 1 1 calc R . . C16B C 0.5655(3) 1.1625(2) 0.67111(18) 0.0330(6) Uani 1 1 d . . . H16B H 0.6048 1.2093 0.6302 0.040 Uiso 1 1 calc R . . C17B C 0.3979(3) 1.0810(2) 0.72001(19) 0.0351(7) Uani 1 1 d . . . H17B H 0.3185 1.0698 0.7131 0.042 Uiso 1 1 calc R . . C18B C 0.4543(2) 1.0247(2) 0.79147(18) 0.0297(6) Uani 1 1 d . . . H18B H 0.4129 0.9784 0.8314 0.036 Uiso 1 1 calc R . . C19B C 0.5695(2) 0.7840(2) 1.07262(17) 0.0274(6) Uani 1 1 d . . . C20B C 0.4496(2) 0.77009(19) 1.06189(17) 0.0266(6) Uani 1 1 d . . . H20B H 0.4097 0.8071 1.0145 0.032 Uiso 1 1 calc R . . C21B C 0.3901(3) 0.7003(2) 1.12269(18) 0.0318(6) Uani 1 1 d . . . H21B H 0.3098 0.6926 1.1146 0.038 Uiso 1 1 calc R . . C22B C 0.5568(3) 0.6581(2) 1.2013(2) 0.0413(8) Uani 1 1 d . . . H22B H 0.5950 0.6196 1.2488 0.050 Uiso 1 1 calc R . . C23B C 0.6226(3) 0.7261(2) 1.1453(2) 0.0390(7) Uani 1 1 d . . . H23B H 0.7020 0.7334 1.1560 0.047 Uiso 1 1 calc R . . O1 O 0.8790(5) 1.0163(4) 0.4770(3) 0.0533(12) Uani 0.50 1 d P . . C1 C 1.0000 1.0000 0.5000 0.0734(17) Uani 1 2 d S . . C2 C 1.0910(8) 1.0250(6) 0.4228(6) 0.067(2) Uani 0.50 1 d P . . C3 C 0.7941(8) 0.9830(6) 0.5479(5) 0.061(2) Uani 0.50 1 d P . . C4 C 0.6639(8) 1.0008(7) 0.5140(6) 0.072(2) Uani 0.50 1 d P . . O2 O 0.7995(5) 0.5067(4) 1.0001(3) 0.0629(14) Uani 0.50 1 d PDU . . C5 C 0.9196(10) 0.4670(7) 1.0237(6) 0.075(3) Uani 0.50 1 d PU . . C6 C 1.0111(11) 0.5130(7) 0.9601(7) 0.073(3) Uani 0.50 1 d PU . . C7 C 0.7000(9) 0.4920(9) 1.0644(6) 0.108(4) Uani 0.50 1 d PDU . . C8 C 0.6541(8) 0.3976(7) 1.0892(6) 0.101(4) Uani 0.50 1 d PDU . . O3 O 0.5093(5) 0.1575(4) 0.3292(4) 0.0655(15) Uani 1 1 d U . . 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 O1A 0.0403(11) 0.0412(12) 0.0280(10) -0.0144(9) 0.0026(8) -0.0118(9) N1A 0.0220(11) 0.0226(11) 0.0238(11) -0.0019(9) -0.0049(8) -0.0019(9) N2A 0.0199(10) 0.0277(11) 0.0213(11) -0.0028(9) -0.0026(8) -0.0043(9) N3A 0.0221(10) 0.0204(11) 0.0193(10) -0.0011(8) -0.0012(8) -0.0019(8) N4A 0.0255(11) 0.0315(13) 0.0336(13) -0.0063(10) -0.0014(9) -0.0032(9) N5A 0.0272(12) 0.0442(15) 0.0350(13) 0.0108(11) 0.0008(10) -0.0037(11) N6A 0.0282(12) 0.0424(15) 0.0390(14) 0.0127(12) -0.0036(10) 0.0002(11) C1A 0.0198(12) 0.0251(13) 0.0211(12) 0.0009(10) -0.0049(10) -0.0018(10) C2A 0.0200(12) 0.0235(13) 0.0239(13) -0.0030(10) -0.0030(10) -0.0018(10) C3A 0.0219(12) 0.0228(13) 0.0202(12) -0.0012(10) -0.0014(10) -0.0043(10) C4A 0.0232(12) 0.0237(13) 0.0250(13) -0.0043(10) -0.0020(10) -0.0055(10) C5A 0.0248(13) 0.0289(14) 0.0216(13) -0.0036(11) -0.0027(10) -0.0049(11) C6A 0.0245(13) 0.0234(13) 0.0239(13) -0.0034(10) -0.0012(10) -0.0025(10) C7A 0.0262(13) 0.0266(14) 0.0215(13) -0.0027(10) -0.0023(10) -0.0056(10) C8A 0.0303(14) 0.0329(15) 0.0282(14) -0.0068(12) -0.0014(11) -0.0085(12) C9A 0.0180(11) 0.0290(14) 0.0240(13) -0.0033(11) -0.0020(10) -0.0023(10) C10A 0.0213(12) 0.0315(14) 0.0248(13) -0.0016(11) -0.0016(10) 0.0013(11) C11A 0.0262(13) 0.0361(16) 0.0253(13) -0.0045(12) -0.0034(11) 0.0000(11) C12A 0.0275(14) 0.0267(14) 0.0354(15) -0.0032(12) 0.0029(11) -0.0049(11) C13A 0.0220(12) 0.0270(14) 0.0259(13) -0.0005(11) -0.0011(10) -0.0022(10) C14A 0.0229(12) 0.0261(13) 0.0241(13) -0.0020(10) -0.0032(10) -0.0049(10) C15A 0.0244(13) 0.0381(16) 0.0337(15) 0.0069(12) -0.0025(11) -0.0014(12) C16A 0.0274(15) 0.0485(19) 0.0369(16) 0.0156(14) -0.0034(12) -0.0007(13) C17A 0.0240(13) 0.0328(15) 0.0318(15) -0.0012(12) 0.0003(11) -0.0016(11) C18A 0.0237(13) 0.0253(13) 0.0258(13) 0.0003(10) -0.0040(10) -0.0030(10) C19A 0.0234(13) 0.0227(13) 0.0265(13) -0.0019(11) -0.0049(10) -0.0029(10) C20A 0.0237(13) 0.0284(14) 0.0257(13) -0.0010(11) -0.0022(10) -0.0047(11) C21A 0.0244(13) 0.0318(15) 0.0349(15) 0.0034(12) -0.0027(11) -0.0014(11) C22A 0.0273(15) 0.0430(18) 0.0379(16) 0.0142(14) -0.0013(12) -0.0049(13) C23A 0.0230(13) 0.0349(15) 0.0324(15) 0.0040(12) -0.0030(11) -0.0038(11) O1B 0.051(3) 0.049(3) 0.032(2) -0.014(2) -0.002(2) -0.018(2) O1C 0.045(2) 0.031(2) 0.041(2) -0.0131(17) -0.0055(18) -0.0029(17) N1B 0.0207(11) 0.0219(11) 0.0307(12) -0.0027(9) -0.0041(9) -0.0021(8) N2B 0.0208(11) 0.0261(11) 0.0234(11) -0.0044(9) -0.0029(8) -0.0020(9) N3B 0.0224(11) 0.0230(11) 0.0250(11) 0.0007(9) -0.0031(9) -0.0039(9) N4B 0.0239(11) 0.0265(12) 0.0271(12) -0.0037(9) -0.0029(9) -0.0037(9) N5B 0.0302(12) 0.0372(14) 0.0328(13) 0.0048(11) -0.0059(10) -0.0059(10) N6B 0.0330(13) 0.0344(14) 0.0383(14) 0.0081(11) -0.0084(10) -0.0091(10) C1B 0.0198(12) 0.0258(13) 0.0246(13) -0.0027(10) -0.0026(10) -0.0023(10) C2B 0.0201(12) 0.0222(13) 0.0261(13) -0.0034(10) -0.0018(10) -0.0030(10) C3B 0.0200(12) 0.0263(13) 0.0246(13) -0.0012(11) -0.0035(10) -0.0019(10) C4B 0.0263(13) 0.0250(14) 0.0376(15) -0.0048(12) -0.0064(11) 0.0014(11) C5B 0.0231(13) 0.0323(15) 0.0291(14) -0.0100(11) 0.0000(11) -0.0027(11) C6B 0.0288(14) 0.0237(13) 0.0302(14) -0.0028(11) -0.0057(11) -0.0055(11) C7B 0.0259(13) 0.0303(15) 0.0328(15) -0.0096(12) -0.0040(11) -0.0025(11) C8B 0.0381(16) 0.0358(16) 0.0474(18) -0.0178(14) -0.0072(14) 0.0012(13) C9B 0.0159(11) 0.0279(14) 0.0244(13) -0.0026(10) -0.0016(10) -0.0018(10) C10B 0.0237(13) 0.0257(13) 0.0278(14) 0.0013(11) -0.0032(10) -0.0033(10) C11B 0.0250(13) 0.0305(14) 0.0234(13) -0.0019(11) -0.0022(10) -0.0041(11) C12B 0.0217(12) 0.0246(13) 0.0261(13) -0.0002(10) -0.0025(10) -0.0037(10) C13B 0.0232(13) 0.0284(14) 0.0231(13) -0.0011(11) -0.0040(10) -0.0025(11) C14B 0.0234(13) 0.0269(14) 0.0237(13) -0.0041(11) -0.0030(10) -0.0023(10) C15B 0.0265(13) 0.0325(15) 0.0294(14) 0.0006(12) -0.0031(11) -0.0055(11) C16B 0.0320(15) 0.0360(16) 0.0289(14) 0.0025(12) -0.0038(11) -0.0083(12) C17B 0.0267(14) 0.0402(17) 0.0341(15) 0.0060(13) -0.0065(12) -0.0044(12) C18B 0.0240(13) 0.0330(15) 0.0298(14) 0.0018(12) -0.0033(11) -0.0046(11) C19B 0.0265(13) 0.0268(14) 0.0272(14) 0.0010(11) -0.0044(11) -0.0032(11) C20B 0.0247(13) 0.0258(14) 0.0278(13) 0.0005(11) -0.0050(10) -0.0032(11) C21B 0.0275(14) 0.0314(15) 0.0338(15) 0.0037(12) -0.0050(11) -0.0070(11) C22B 0.0339(16) 0.0415(18) 0.0420(17) 0.0170(14) -0.0146(13) -0.0091(13) C23B 0.0276(15) 0.0397(17) 0.0450(18) 0.0121(14) -0.0127(13) -0.0089(13) O1 0.065(3) 0.046(3) 0.046(3) -0.004(2) -0.004(2) -0.002(2) C1 0.069(4) 0.080(4) 0.064(4) 0.001(3) -0.013(3) 0.003(3) C2 0.071(6) 0.049(5) 0.074(6) -0.005(4) 0.006(4) -0.003(4) C3 0.074(5) 0.061(5) 0.043(4) -0.011(4) 0.014(4) -0.004(4) C4 0.064(5) 0.068(5) 0.083(6) -0.025(5) -0.008(4) 0.012(4) O2 0.080(4) 0.051(3) 0.054(3) -0.001(2) -0.014(3) 0.005(3) C5 0.094(7) 0.062(5) 0.068(6) 0.001(4) -0.040(5) -0.002(5) C6 0.080(6) 0.055(5) 0.095(6) -0.032(5) -0.036(6) 0.011(4) C7 0.100(7) 0.155(10) 0.055(5) 0.027(6) 0.000(5) -0.044(7) C8 0.099(7) 0.123(8) 0.105(7) -0.088(7) -0.055(6) 0.044(6) O3 0.083(4) 0.063(3) 0.055(3) -0.026(3) -0.012(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 O1A C8A 1.427(3) . ? O1A H1A 0.9034 . ? N1A C1A 1.486(3) . ? N1A C3A 1.488(3) . ? N1A C4A 1.490(3) . ? N2A C1A 1.479(3) . ? N2A C5A 1.487(3) . ? N2A C2A 1.487(3) . ? N3A C2A 1.473(3) . ? N3A C3A 1.476(3) . ? N3A C6A 1.488(3) . ? N4A C12A 1.342(4) . ? N4A C11A 1.348(4) . ? N5A C17A 1.338(3) . ? N5A C16A 1.347(4) . ? N6A C21A 1.337(4) . ? N6A C22A 1.341(4) . ? C1A C9A 1.516(4) . ? C1A H1B 0.9800 . ? C2A C14A 1.518(3) . ? C2A H2A 0.9800 . ? C3A C19A 1.517(3) . ? C3A H3A 0.9800 . ? C4A C7A 1.539(3) . ? C4A H4A1 0.9700 . ? C4A H4A2 0.9700 . ? C5A C7A 1.536(3) . ? C5A H5A1 0.9700 . ? C5A H5A2 0.9700 . ? C6A C7A 1.532(3) . ? C6A H6A1 0.9700 . ? C6A H6A2 0.9700 . ? C7A C8A 1.513(4) . ? C8A H8A1 0.9700 . ? C8A H8A2 0.9700 . ? C9A C10A 1.394(4) . ? C9A C13A 1.393(4) . ? C10A C11A 1.386(4) . ? C10A H10A 0.9300 . ? C11A H11A 0.9300 . ? C12A C13A 1.388(4) . ? C12A H12A 0.9300 . ? C13A H13A 0.9300 . ? C14A C18A 1.390(4) . ? C14A C15A 1.391(4) . ? C15A C16A 1.378(4) . ? C15A H15A 0.9300 . ? C16A H16A 0.9300 . ? C17A C18A 1.384(4) . ? C17A H17A 0.9300 . ? C18A H18A 0.9300 . ? C19A C23A 1.385(4) . ? C19A C20A 1.391(4) . ? C20A C21A 1.378(4) . ? C20A H20A 0.9300 . ? C21A H21A 0.9300 . ? C22A C23A 1.383(4) . ? C22A H22A 0.9300 . ? C23A H23A 0.9300 . ? O1B C8B 1.522(5) . ? O1C C8B 1.492(5) . ? N1B C3B 1.484(3) . ? N1B C1B 1.487(3) . ? N1B C4B 1.489(3) . ? N2B C2B 1.483(3) . ? N2B C5B 1.483(3) . ? N2B C1B 1.491(3) . ? N3B C3B 1.479(3) . ? N3B C2B 1.479(3) . ? N3B C6B 1.483(3) . ? N4B C12B 1.345(3) . ? N4B C11B 1.349(3) . ? N5B C17B 1.338(4) . ? N5B C16B 1.343(4) . ? N6B C21B 1.340(3) . ? N6B C22B 1.342(4) . ? C1B C9B 1.508(4) . ? C1B H1C 0.9800 . ? C2B C14B 1.519(3) . ? C2B H2B 0.9800 . ? C3B C19B 1.513(4) . ? C3B H3B 0.9800 . ? C4B C7B 1.536(4) . ? C4B H4B1 0.9700 . ? C4B H4B2 0.9700 . ? C5B C7B 1.539(4) . ? C5B H5B1 0.9700 . ? C5B H5B2 0.9700 . ? C6B C7B 1.542(4) . ? C6B H6B1 0.9700 . ? C6B H6B2 0.9700 . ? C7B C8B 1.528(4) . ? C9B C10B 1.399(3) . ? C9B C13B 1.396(4) . ? C10B C11B 1.379(4) . ? C10B H10B 0.9300 . ? C11B H11B 0.9300 . ? C12B C13B 1.378(4) . ? C12B H12B 0.9300 . ? C13B H13B 0.9300 . ? C14B C15B 1.380(4) . ? C14B C18B 1.398(4) . ? C15B C16B 1.390(4) . ? C15B H15B 0.9300 . ? C16B H16B 0.9300 . ? C17B C18B 1.385(4) . ? C17B H17B 0.9300 . ? C18B H18B 0.9300 . ? C19B C23B 1.391(4) . ? C19B C20B 1.393(4) . ? C20B C21B 1.389(4) . ? C20B H20B 0.9300 . ? C21B H21B 0.9300 . ? C22B C23B 1.376(4) . ? C22B H22B 0.9300 . ? C23B H23B 0.9300 . ? O1 C1 1.401(5) . ? O1 C3 1.412(9) . ? C1 C2 1.496(9) . ? C3 C4 1.559(12) . ? O2 C7 1.412(8) . ? O2 C5 1.433(11) . ? C5 C6 1.451(16) . ? C7 C8 1.434(9) . ? 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 C8A O1A H1A 112.8 . . ? C1A N1A C3A 108.08(19) . . ? C1A N1A C4A 106.88(18) . . ? C3A N1A C4A 109.55(19) . . ? C1A N2A C5A 107.07(19) . . ? C1A N2A C2A 108.51(18) . . ? C5A N2A C2A 109.22(19) . . ? C2A N3A C3A 105.82(18) . . ? C2A N3A C6A 109.75(18) . . ? C3A N3A C6A 110.05(19) . . ? C12A N4A C11A 116.4(2) . . ? C17A N5A C16A 115.5(2) . . ? C21A N6A C22A 115.9(2) . . ? N2A C1A N1A 113.3(2) . . ? N2A C1A C9A 112.5(2) . . ? N1A C1A C9A 112.72(19) . . ? N2A C1A H1B 105.8 . . ? N1A C1A H1B 105.8 . . ? C9A C1A H1B 105.8 . . ? N3A C2A N2A 112.8(2) . . ? N3A C2A C14A 111.8(2) . . ? N2A C2A C14A 112.34(19) . . ? N3A C2A H2A 106.4 . . ? N2A C2A H2A 106.4 . . ? C14A C2A H2A 106.4 . . ? N3A C3A N1A 112.70(19) . . ? N3A C3A C19A 112.0(2) . . ? N1A C3A C19A 112.7(2) . . ? N3A C3A H3A 106.3 . . ? N1A C3A H3A 106.3 . . ? C19A C3A H3A 106.3 . . ? N1A C4A C7A 111.0(2) . . ? N1A C4A H4A1 109.4 . . ? C7A C4A H4A1 109.4 . . ? N1A C4A H4A2 109.4 . . ? C7A C4A H4A2 109.4 . . ? H4A1 C4A H4A2 108.0 . . ? N2A C5A C7A 111.03(19) . . ? N2A C5A H5A1 109.4 . . ? C7A C5A H5A1 109.4 . . ? N2A C5A H5A2 109.4 . . ? C7A C5A H5A2 109.4 . . ? H5A1 C5A H5A2 108.0 . . ? N3A C6A C7A 111.4(2) . . ? N3A C6A H6A1 109.4 . . ? C7A C6A H6A1 109.4 . . ? N3A C6A H6A2 109.4 . . ? C7A C6A H6A2 109.4 . . ? H6A1 C6A H6A2 108.0 . . ? C8A C7A C6A 111.0(2) . . ? C8A C7A C5A 111.7(2) . . ? C6A C7A C5A 106.8(2) . . ? C8A C7A C4A 111.2(2) . . ? C6A C7A C4A 106.8(2) . . ? C5A C7A C4A 109.1(2) . . ? O1A C8A C7A 108.7(2) . . ? O1A C8A H8A1 110.0 . . ? C7A C8A H8A1 110.0 . . ? O1A C8A H8A2 110.0 . . ? C7A C8A H8A2 110.0 . . ? H8A1 C8A H8A2 108.3 . . ? C10A C9A C13A 117.4(2) . . ? C10A C9A C1A 121.5(2) . . ? C13A C9A C1A 120.9(2) . . ? C11A C10A C9A 119.4(2) . . ? C11A C10A H10A 120.3 . . ? C9A C10A H10A 120.3 . . ? N4A C11A C10A 123.7(3) . . ? N4A C11A H11A 118.2 . . ? C10A C11A H11A 118.2 . . ? N4A C12A C13A 123.9(3) . . ? N4A C12A H12A 118.1 . . ? C13A C12A H12A 118.1 . . ? C12A C13A C9A 119.3(2) . . ? C12A C13A H13A 120.4 . . ? C9A C13A H13A 120.4 . . ? C18A C14A C15A 116.9(2) . . ? C18A C14A C2A 122.1(2) . . ? C15A C14A C2A 120.8(2) . . ? C16A C15A C14A 119.5(3) . . ? C16A C15A H15A 120.2 . . ? C14A C15A H15A 120.2 . . ? N5A C16A C15A 124.3(3) . . ? N5A C16A H16A 117.8 . . ? C15A C16A H16A 117.8 . . ? N5A C17A C18A 124.3(2) . . ? N5A C17A H17A 117.8 . . ? C18A C17A H17A 117.8 . . ? C17A C18A C14A 119.4(2) . . ? C17A C18A H18A 120.3 . . ? C14A C18A H18A 120.3 . . ? C23A C19A C20A 117.2(2) . . ? C23A C19A C3A 121.2(2) . . ? C20A C19A C3A 121.4(2) . . ? C21A C20A C19A 119.5(2) . . ? C21A C20A H20A 120.3 . . ? C19A C20A H20A 120.3 . . ? N6A C21A C20A 124.1(3) . . ? N6A C21A H21A 118.0 . . ? C20A C21A H21A 118.0 . . ? N6A C22A C23A 124.1(3) . . ? N6A C22A H22A 117.9 . . ? C23A C22A H22A 117.9 . . ? C22A C23A C19A 119.2(2) . . ? C22A C23A H23A 120.4 . . ? C19A C23A H23A 120.4 . . ? C3B N1B C1B 108.06(19) . . ? C3B N1B C4B 109.36(19) . . ? C1B N1B C4B 106.8(2) . . ? C2B N2B C5B 109.57(19) . . ? C2B N2B C1B 107.94(19) . . ? C5B N2B C1B 107.25(19) . . ? C3B N3B C2B 105.22(19) . . ? C3B N3B C6B 110.47(19) . . ? C2B N3B C6B 109.9(2) . . ? C12B N4B C11B 117.0(2) . . ? C17B N5B C16B 115.9(2) . . ? C21B N6B C22B 115.6(2) . . ? N1B C1B N2B 113.09(19) . . ? N1B C1B C9B 112.3(2) . . ? N2B C1B C9B 113.0(2) . . ? N1B C1B H1C 105.9 . . ? N2B C1B H1C 105.9 . . ? C9B C1B H1C 105.9 . . ? N3B C2B N2B 113.11(19) . . ? N3B C2B C14B 112.3(2) . . ? N2B C2B C14B 112.4(2) . . ? N3B C2B H2B 106.1 . . ? N2B C2B H2B 106.1 . . ? C14B C2B H2B 106.1 . . ? N3B C3B N1B 113.1(2) . . ? N3B C3B C19B 111.8(2) . . ? N1B C3B C19B 112.3(2) . . ? N3B C3B H3B 106.4 . . ? N1B C3B H3B 106.4 . . ? C19B C3B H3B 106.4 . . ? N1B C4B C7B 111.3(2) . . ? N1B C4B H4B1 109.4 . . ? C7B C4B H4B1 109.4 . . ? N1B C4B H4B2 109.4 . . ? C7B C4B H4B2 109.4 . . ? H4B1 C4B H4B2 108.0 . . ? N2B C5B C7B 111.0(2) . . ? N2B C5B H5B1 109.4 . . ? C7B C5B H5B1 109.4 . . ? N2B C5B H5B2 109.4 . . ? C7B C5B H5B2 109.4 . . ? H5B1 C5B H5B2 108.0 . . ? N3B C6B C7B 110.8(2) . . ? N3B C6B H6B1 109.5 . . ? C7B C6B H6B1 109.5 . . ? N3B C6B H6B2 109.5 . . ? C7B C6B H6B2 109.5 . . ? H6B1 C6B H6B2 108.1 . . ? C8B C7B C4B 111.1(2) . . ? C8B C7B C5B 111.0(2) . . ? C4B C7B C5B 108.9(2) . . ? C8B C7B C6B 111.5(2) . . ? C4B C7B C6B 107.2(2) . . ? C5B C7B C6B 106.9(2) . . ? O1C C8B C7B 109.8(3) . . ? O1B C8B C7B 111.5(3) . . ? C10B C9B C13B 116.9(2) . . ? C10B C9B C1B 121.1(2) . . ? C13B C9B C1B 121.8(2) . . ? C11B C10B C9B 119.5(2) . . ? C11B C10B H10B 120.2 . . ? C9B C10B H10B 120.2 . . ? N4B C11B C10B 123.4(2) . . ? N4B C11B H11B 118.3 . . ? C10B C11B H11B 118.3 . . ? N4B C12B C13B 123.0(2) . . ? N4B C12B H12B 118.5 . . ? C13B C12B H12B 118.5 . . ? C12B C13B C9B 120.1(2) . . ? C12B C13B H13B 120.0 . . ? C9B C13B H13B 120.0 . . ? C15B C14B C18B 117.1(2) . . ? C15B C14B C2B 121.7(2) . . ? C18B C14B C2B 121.0(2) . . ? C14B C15B C16B 120.1(3) . . ? C14B C15B H15B 120.0 . . ? C16B C15B H15B 120.0 . . ? N5B C16B C15B 123.5(3) . . ? N5B C16B H16B 118.3 . . ? C15B C16B H16B 118.3 . . ? N5B C17B C18B 124.7(3) . . ? N5B C17B H17B 117.6 . . ? C18B C17B H17B 117.6 . . ? C17B C18B C14B 118.8(3) . . ? C17B C18B H18B 120.6 . . ? C14B C18B H18B 120.6 . . ? C23B C19B C20B 116.9(2) . . ? C23B C19B C3B 121.7(2) . . ? C20B C19B C3B 121.2(2) . . ? C21B C20B C19B 119.3(2) . . ? C21B C20B H20B 120.4 . . ? C19B C20B H20B 120.4 . . ? N6B C21B C20B 124.1(2) . . ? N6B C21B H21B 117.9 . . ? C20B C21B H21B 117.9 . . ? N6B C22B C23B 124.5(3) . . ? N6B C22B H22B 117.7 . . ? C23B C22B H22B 117.7 . . ? C22B C23B C19B 119.5(3) . . ? C22B C23B H23B 120.2 . . ? C19B C23B H23B 120.2 . . ? C1 O1 C3 113.0(5) . . ? O1 C1 C2 113.0(4) . . ? O1 C3 C4 108.5(6) . . ? C7 O2 C5 118.7(7) . . ? O2 C5 C6 110.2(7) . . ? O2 C7 C8 120.3(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 O1A H1A N4B 0.90 1.88 2.764(3) 167.1 2_677 data_8 _database_code_depnum_ccdc_archive 'CCDC 845928' #TrackingRef 'resub.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H30 N6 O2' _chemical_formula_weight 446.55 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'I b a 2' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1/2, z+1/2' 'x+1, -y+1, z+1/2' '-x+1, y+1, z+1/2' _cell_length_a 17.5800(14) _cell_length_b 21.6924(16) _cell_length_c 12.8140(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4886.7(6) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 42880 _cell_measurement_theta_min 2.72 _cell_measurement_theta_max 25.68 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 __exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.214 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1904 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type none _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 scans with 2\% steps' _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 42880 _diffrn_reflns_av_R_equivalents 0.0718 _diffrn_reflns_av_sigmaI/netI 0.1163 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.72 _diffrn_reflns_theta_max 25.68 _reflns_number_total 2433 _reflns_number_gt 1806 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 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 atom bound to O1 was 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 times that of the parent atom. Some voids in the lattice indicate the presence of unresolved solvent molecules, which have been taken into account with the program SQUEEZE. In the absence of a suitable scatterer, the Friedel pairs have been merged. 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^)+(0.0865P)^2^+1.0884P] 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 ? _refine_ls_number_reflns 2433 _refine_ls_number_parameters 271 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1332 _refine_ls_R_factor_gt 0.0804 _refine_ls_wR_factor_ref 0.1920 _refine_ls_wR_factor_gt 0.1698 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _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 0.220 _refine_diff_density_min -0.221 _refine_diff_density_rms 0.053 # SQUEEZE RESULTS (APPEND TO CIF)# loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons 1 0.000 0.000 0.136 66.7 27.1 2 0.000 0.500 0.067 472.7 92.8 3 0.500 1.000 0.055 472.7 92.8 4 0.500 0.500 0.136 66.7 27.1 5 0.000 0.000 0.636 66.7 27.1 6 0.500 0.500 0.636 66.7 27.1 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 O1 O 0.64942(19) 0.09559(15) 0.1740(3) 0.0405(9) Uani 1 1 d . . . H1 H 0.6775 0.0616 0.1523 0.049 Uiso 1 1 d R . . N1 N 0.8446(2) 0.16192(18) 0.3535(3) 0.0316(10) Uani 1 1 d . . . N2 N 0.8117(2) 0.26582(18) 0.2935(3) 0.0320(9) Uani 1 1 d . . . N3 N 0.7294(2) 0.21289(17) 0.4198(3) 0.0307(9) Uani 1 1 d . . . N4 N 1.0507(3) 0.2217(3) 0.0862(4) 0.0524(13) Uani 1 1 d . . . N5 N 0.6032(3) 0.4217(2) 0.3676(4) 0.0491(13) Uani 1 1 d . . . N6 N 0.7259(3) 0.0038(2) 0.5995(4) 0.0492(12) Uani 1 1 d . . . C1 C 0.8734(3) 0.2230(2) 0.3216(4) 0.0301(11) Uani 1 1 d . . . H1A H 0.8987 0.2406 0.3830 0.036 Uiso 1 1 calc R . . C2 C 0.7631(3) 0.2718(2) 0.3868(3) 0.0306(11) Uani 1 1 d . . . H2 H 0.7972 0.2842 0.4435 0.037 Uiso 1 1 calc R . . C3 C 0.7949(3) 0.1716(2) 0.4444(4) 0.0311(11) Uani 1 1 d . . . H3 H 0.8256 0.1934 0.4964 0.037 Uiso 1 1 calc R . . C4 C 0.7997(3) 0.1346(2) 0.2662(3) 0.0309(11) Uani 1 1 d . . . H4A H 0.7800 0.0947 0.2872 0.037 Uiso 1 1 calc R . . H4B H 0.8325 0.1285 0.2061 0.037 Uiso 1 1 calc R . . C5 C 0.7670(3) 0.2398(2) 0.2070(3) 0.0302(11) Uani 1 1 d . . . H5A H 0.7994 0.2352 0.1462 0.036 Uiso 1 1 calc R . . H5B H 0.7262 0.2680 0.1891 0.036 Uiso 1 1 calc R . . C6 C 0.6841(3) 0.1869(2) 0.3338(3) 0.0317(11) Uani 1 1 d . . . H6A H 0.6425 0.2147 0.3174 0.038 Uiso 1 1 calc R . . H6B H 0.6626 0.1478 0.3554 0.038 Uiso 1 1 calc R . . C7 C 0.7332(3) 0.1772(2) 0.2361(4) 0.0306(11) Uani 1 1 d . . . C8 C 0.6878(3) 0.1508(2) 0.1461(4) 0.0341(11) Uani 1 1 d . . . H8A H 0.6508 0.1811 0.1231 0.041 Uiso 1 1 calc R . . H8B H 0.7218 0.1425 0.0881 0.041 Uiso 1 1 calc R . . C9 C 0.9326(3) 0.2209(2) 0.2357(4) 0.0362(12) Uani 1 1 d . . . C10 C 0.9779(3) 0.1684(3) 0.2194(4) 0.0424(13) Uani 1 1 d . . . H10 H 0.9699 0.1328 0.2583 0.051 Uiso 1 1 calc R . . C11 C 1.0355(3) 0.1707(3) 0.1438(5) 0.0519(16) Uani 1 1 d . . . H11 H 1.0646 0.1355 0.1325 0.062 Uiso 1 1 calc R . . C12 C 1.0062(3) 0.2715(3) 0.1063(4) 0.0473(14) Uani 1 1 d . . . H12 H 1.0151 0.3072 0.0682 0.057 Uiso 1 1 calc R . . C13 C 0.9497(3) 0.2725(3) 0.1780(4) 0.0458(14) Uani 1 1 d . . . H13 H 0.9221 0.3085 0.1884 0.055 Uiso 1 1 calc R . . C14 C 0.7042(3) 0.3235(2) 0.3773(4) 0.0352(12) Uani 1 1 d . . . C15 C 0.7195(4) 0.3735(2) 0.3173(4) 0.0515(16) Uani 1 1 d . . . H15 H 0.7644 0.3754 0.2791 0.062 Uiso 1 1 calc R . . C16 C 0.6678(4) 0.4218(3) 0.3132(5) 0.0535(16) Uani 1 1 d . . . H16 H 0.6786 0.4555 0.2709 0.064 Uiso 1 1 calc R . . C17 C 0.5881(3) 0.3727(2) 0.4248(4) 0.0421(13) Uani 1 1 d . . . H17 H 0.5427 0.3716 0.4621 0.051 Uiso 1 1 calc R . . C18 C 0.6366(3) 0.3229(2) 0.4316(4) 0.0394(12) Uani 1 1 d . . . H18 H 0.6238 0.2891 0.4727 0.047 Uiso 1 1 calc R . . C19 C 0.7698(3) 0.1110(2) 0.4956(4) 0.0326(11) Uani 1 1 d . . . C20 C 0.7004(3) 0.1079(3) 0.5490(4) 0.0407(13) Uani 1 1 d . . . H20 H 0.6680 0.1418 0.5520 0.049 Uiso 1 1 calc R . . C21 C 0.6816(3) 0.0529(2) 0.5972(4) 0.0440(14) Uani 1 1 d . . . H21 H 0.6346 0.0503 0.6301 0.053 Uiso 1 1 calc R . . C22 C 0.7929(3) 0.0085(2) 0.5495(4) 0.0436(14) Uani 1 1 d . . . H22 H 0.8257 -0.0251 0.5516 0.052 Uiso 1 1 calc R . . C23 C 0.8159(3) 0.0604(2) 0.4950(4) 0.0415(13) Uani 1 1 d . . . H23 H 0.8618 0.0607 0.4588 0.050 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 O1 0.037(2) 0.0295(18) 0.054(2) -0.0068(16) 0.0002(18) -0.0009(16) N1 0.032(2) 0.030(2) 0.032(2) -0.0042(18) -0.0080(19) 0.0046(19) N2 0.030(2) 0.036(2) 0.029(2) -0.0045(19) -0.0025(19) -0.0024(19) N3 0.033(3) 0.027(2) 0.032(2) 0.0018(18) -0.0024(19) -0.0020(18) N4 0.037(3) 0.079(4) 0.041(3) -0.001(3) 0.007(2) -0.008(3) N5 0.055(4) 0.034(3) 0.058(3) -0.007(2) -0.006(3) 0.015(2) N6 0.063(3) 0.036(3) 0.050(3) 0.011(2) -0.006(3) 0.001(2) C1 0.020(3) 0.031(3) 0.039(3) -0.007(2) -0.006(2) -0.001(2) C2 0.032(3) 0.033(3) 0.027(2) -0.004(2) 0.002(2) -0.002(2) C3 0.026(3) 0.034(3) 0.034(3) -0.001(2) 0.002(2) 0.003(2) C4 0.025(3) 0.035(3) 0.034(3) -0.004(2) -0.001(2) 0.005(2) C5 0.035(3) 0.033(3) 0.023(2) 0.001(2) -0.004(2) -0.001(2) C6 0.034(3) 0.039(3) 0.022(2) -0.001(2) -0.009(2) 0.001(2) C7 0.023(3) 0.036(3) 0.033(3) 0.000(2) -0.004(2) -0.004(2) C8 0.038(3) 0.025(3) 0.039(3) -0.003(2) 0.000(2) 0.000(2) C9 0.018(3) 0.047(3) 0.044(3) -0.002(3) 0.001(2) -0.005(2) C10 0.032(3) 0.049(3) 0.046(3) 0.011(3) -0.002(2) 0.003(2) C11 0.032(3) 0.065(4) 0.059(4) -0.003(3) 0.001(3) 0.006(3) C12 0.035(3) 0.061(4) 0.046(3) 0.009(3) 0.010(3) 0.003(3) C13 0.021(3) 0.062(4) 0.054(3) -0.003(3) -0.005(3) -0.006(3) C14 0.047(3) 0.027(3) 0.032(3) -0.008(2) -0.007(2) 0.003(2) C15 0.067(4) 0.029(3) 0.058(4) 0.009(3) 0.017(3) 0.003(3) C16 0.069(5) 0.031(3) 0.060(4) 0.000(3) -0.001(4) 0.009(3) C17 0.043(3) 0.049(3) 0.034(3) -0.002(3) 0.000(3) 0.012(3) C18 0.034(3) 0.048(3) 0.037(3) 0.000(2) 0.013(3) 0.006(3) C19 0.042(3) 0.027(2) 0.029(2) 0.001(2) -0.003(2) 0.003(2) C20 0.036(3) 0.046(3) 0.040(3) 0.001(2) -0.001(3) 0.006(3) C21 0.056(4) 0.036(3) 0.040(3) 0.013(3) 0.007(3) 0.002(3) C22 0.046(4) 0.032(3) 0.053(3) -0.001(2) 0.004(3) 0.010(3) C23 0.044(4) 0.030(3) 0.050(3) 0.009(2) -0.001(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 O1 C8 1.420(5) . ? O1 H1 0.9293 . ? N1 C3 1.470(6) . ? N1 C1 1.476(6) . ? N1 C4 1.492(6) . ? N2 C5 1.471(6) . ? N2 C1 1.473(6) . ? N2 C2 1.476(6) . ? N3 C6 1.472(6) . ? N3 C2 1.470(6) . ? N3 C3 1.491(6) . ? N4 C11 1.357(7) . ? N4 C12 1.358(7) . ? N5 C17 1.319(7) . ? N5 C16 1.333(8) . ? N6 C21 1.319(7) . ? N6 C22 1.343(7) . ? C1 C9 1.515(7) . ? C1 H1A 0.9800 . ? C2 C14 1.531(7) . ? C2 H2 0.9800 . ? C3 C19 1.534(6) . ? C3 H3 0.9800 . ? C4 C7 1.538(6) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C7 1.528(6) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.535(6) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.516(6) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C13 1.375(7) . ? C9 C10 1.404(7) . ? C10 C11 1.402(7) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 C13 1.354(8) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C15 1.356(7) . ? C14 C18 1.377(7) . ? C15 C16 1.388(8) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 C18 1.378(7) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 C23 1.366(7) . ? C19 C20 1.400(7) . ? C20 C21 1.385(7) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? C22 C23 1.385(7) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? 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 C8 O1 H1 110.0 . . ? C3 N1 C1 107.1(3) . . ? C3 N1 C4 109.7(4) . . ? C1 N1 C4 109.3(4) . . ? C5 N2 C1 109.7(4) . . ? C5 N2 C2 109.5(4) . . ? C1 N2 C2 106.5(4) . . ? C6 N3 C2 109.5(4) . . ? C6 N3 C3 110.2(3) . . ? C2 N3 C3 105.8(4) . . ? C11 N4 C12 115.6(5) . . ? C17 N5 C16 117.6(5) . . ? C21 N6 C22 116.5(5) . . ? N2 C1 N1 112.4(4) . . ? N2 C1 C9 110.3(4) . . ? N1 C1 C9 114.2(4) . . ? N2 C1 H1A 106.5 . . ? N1 C1 H1A 106.5 . . ? C9 C1 H1A 106.5 . . ? N3 C2 N2 112.9(4) . . ? N3 C2 C14 112.8(4) . . ? N2 C2 C14 113.1(4) . . ? N3 C2 H2 105.7 . . ? N2 C2 H2 105.7 . . ? C14 C2 H2 105.7 . . ? N1 C3 N3 112.2(4) . . ? N1 C3 C19 112.8(4) . . ? N3 C3 C19 112.5(4) . . ? N1 C3 H3 106.3 . . ? N3 C3 H3 106.3 . . ? C19 C3 H3 106.3 . . ? N1 C4 C7 110.6(4) . . ? N1 C4 H4A 109.5 . . ? C7 C4 H4A 109.5 . . ? N1 C4 H4B 109.5 . . ? C7 C4 H4B 109.5 . . ? H4A C4 H4B 108.1 . . ? N2 C5 C7 111.4(4) . . ? N2 C5 H5A 109.4 . . ? C7 C5 H5A 109.4 . . ? N2 C5 H5B 109.4 . . ? C7 C5 H5B 109.4 . . ? H5A C5 H5B 108.0 . . ? N3 C6 C7 111.0(4) . . ? N3 C6 H6A 109.4 . . ? C7 C6 H6A 109.4 . . ? N3 C6 H6B 109.4 . . ? C7 C6 H6B 109.4 . . ? H6A C6 H6B 108.0 . . ? C8 C7 C5 110.8(4) . . ? C8 C7 C6 112.1(4) . . ? C5 C7 C6 107.2(4) . . ? C8 C7 C4 111.3(4) . . ? C5 C7 C4 107.5(4) . . ? C6 C7 C4 107.8(4) . . ? O1 C8 C7 112.2(4) . . ? O1 C8 H8A 109.2 . . ? C7 C8 H8A 109.2 . . ? O1 C8 H8B 109.2 . . ? C7 C8 H8B 109.2 . . ? H8A C8 H8B 107.9 . . ? C13 C9 C10 117.1(5) . . ? C13 C9 C1 121.0(5) . . ? C10 C9 C1 121.5(5) . . ? C11 C10 C9 119.0(5) . . ? C11 C10 H10 120.5 . . ? C9 C10 H10 120.5 . . ? N4 C11 C10 123.1(6) . . ? N4 C11 H11 118.5 . . ? C10 C11 H11 118.5 . . ? C13 C12 N4 124.4(6) . . ? C13 C12 H12 117.8 . . ? N4 C12 H12 117.8 . . ? C12 C13 C9 120.8(6) . . ? C12 C13 H13 119.6 . . ? C9 C13 H13 119.6 . . ? C15 C14 C18 117.7(5) . . ? C15 C14 C2 119.8(5) . . ? C18 C14 C2 122.4(4) . . ? C14 C15 C16 119.7(6) . . ? C14 C15 H15 120.1 . . ? C16 C15 H15 120.1 . . ? N5 C16 C15 122.5(6) . . ? N5 C16 H16 118.8 . . ? C15 C16 H16 118.8 . . ? N5 C17 C18 122.9(5) . . ? N5 C17 H17 118.6 . . ? C18 C17 H17 118.6 . . ? C14 C18 C17 119.6(5) . . ? C14 C18 H18 120.2 . . ? C17 C18 H18 120.2 . . ? C23 C19 C20 118.8(5) . . ? C23 C19 C3 121.0(5) . . ? C20 C19 C3 120.0(4) . . ? C21 C20 C19 117.9(5) . . ? C21 C20 H20 121.1 . . ? C19 C20 H20 121.1 . . ? N6 C21 C20 124.3(5) . . ? N6 C21 H21 117.8 . . ? C20 C21 H21 117.8 . . ? N6 C22 C23 124.0(5) . . ? N6 C22 H22 118.0 . . ? C23 C22 H22 118.0 . . ? C19 C23 C22 118.4(5) . . ? C19 C23 H23 120.8 . . ? C22 C23 H23 120.8 . . ? 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 O1 H1 N6 0.93 1.79 2.715(6) 174.5 7_444 #===END data_9 _database_code_depnum_ccdc_archive 'CCDC 845929' #TrackingRef 'combined_final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H24 Co F18 N6 O P3' _chemical_formula_weight 894.32 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 '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/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 10.1138(4) _cell_length_b 18.5737(10) _cell_length_c 16.9353(7) _cell_angle_alpha 90.00 _cell_angle_beta 97.817(3) _cell_angle_gamma 90.00 _cell_volume 3151.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 93124 _cell_measurement_theta_min 2.19 _cell_measurement_theta_max 25.68 _exptl_crystal_description parallelepiped _exptl_crystal_colour 'translucent light yellow' _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.885 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1784 _exptl_absorpt_coefficient_mu 0.837 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.687 _exptl_absorpt_correction_T_max 0.920 _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 four \w scans with 2\% steps (400 frames)' _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 93124 _diffrn_reflns_av_R_equivalents 0.0332 _diffrn_reflns_av_sigmaI/netI 0.0384 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 25.68 _reflns_number_total 5992 _reflns_number_gt 5026 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1998)' _computing_cell_refinement 'HKL2000 (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL2000 (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008); 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. O1 was found to be disordered over two positions which were refined with occupancy parameters constrained to sum to unity. Only the H atom bound to the most populated position O1A was found on a Fourier-difference map. The C-bound H atoms were introduced at calculated positions. All were treated as riding atoms with an isotropic displacement parameter equal to 1.2 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^)+(0.0387P)^2^+1.7710P] 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 5992 _refine_ls_number_parameters 479 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0430 _refine_ls_R_factor_gt 0.0331 _refine_ls_wR_factor_ref 0.0860 _refine_ls_wR_factor_gt 0.0820 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0.001 _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 0.613 _refine_diff_density_min -0.489 _refine_diff_density_rms 0.062 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 Co Co 0.71725(3) 0.240625(16) 0.849740(16) 0.02058(9) Uani 1 1 d . . . P1 P 0.69883(6) 0.16608(3) 0.48255(3) 0.02801(15) Uani 1 1 d . . . P2 P 0.14302(6) 0.07533(4) 0.12089(4) 0.02906(15) Uani 1 1 d . . . P3 P 1.39479(6) 0.03150(3) 0.76628(4) 0.02645(14) Uani 1 1 d . . . O1A O 1.1351(2) 0.18643(13) 0.70451(14) 0.0356(7) Uani 0.767(5) 1 d P . . H1 H 1.2091 0.1556 0.7269 0.043 Uiso 0.767(5) 1 d PR . . O1B O 1.0394(7) 0.1839(4) 0.6333(4) 0.032(2) Uani 0.233(5) 1 d P . . N1 N 0.68418(18) 0.17970(10) 0.75909(11) 0.0245(4) Uani 1 1 d . . . N2 N 0.83206(18) 0.29411(10) 0.79187(11) 0.0244(4) Uani 1 1 d . . . N3 N 0.86571(17) 0.18146(10) 0.88779(10) 0.0226(4) Uani 1 1 d . . . N4 N 0.55267(18) 0.28688(10) 0.80145(10) 0.0231(4) Uani 1 1 d . . . N5 N 0.75546(17) 0.31853(10) 0.92575(11) 0.0226(4) Uani 1 1 d . . . N6 N 0.62831(17) 0.18194(10) 0.92172(10) 0.0220(4) Uani 1 1 d . . . F1 F 0.63553(14) 0.11608(8) 0.41036(8) 0.0348(3) Uani 1 1 d . . . F2 F 0.83969(14) 0.12674(9) 0.48232(9) 0.0417(4) Uani 1 1 d . . . F3 F 0.65756(15) 0.10753(8) 0.54489(8) 0.0390(4) Uani 1 1 d . . . F4 F 0.55767(14) 0.20512(8) 0.48317(8) 0.0359(3) Uani 1 1 d . . . F5 F 0.73908(13) 0.22433(8) 0.42030(8) 0.0366(3) Uani 1 1 d . . . F6 F 0.76250(15) 0.21539(9) 0.55515(9) 0.0415(4) Uani 1 1 d . . . F7 F 0.1841(2) -0.00642(9) 0.12758(10) 0.0582(5) Uani 1 1 d . . . F8 F 0.13682(16) 0.07730(10) 0.21465(9) 0.0500(4) Uani 1 1 d . . . F9 F 0.29651(15) 0.09796(10) 0.13635(9) 0.0468(4) Uani 1 1 d . . . F10 F 0.14941(16) 0.07321(11) 0.02737(9) 0.0514(4) Uani 1 1 d . . . F11 F -0.01022(16) 0.05502(13) 0.10555(11) 0.0693(6) Uani 1 1 d . . . F12 F 0.1055(2) 0.15860(11) 0.11480(15) 0.0830(7) Uani 1 1 d . . . F13 F 1.26680(15) 0.02225(8) 0.70006(9) 0.0419(4) Uani 1 1 d . . . F14 F 1.41721(13) -0.05376(7) 0.76822(8) 0.0313(3) Uani 1 1 d . . . F15 F 1.30114(15) 0.02477(8) 0.83401(9) 0.0414(4) Uani 1 1 d . . . F16 F 1.37096(14) 0.11785(8) 0.76386(9) 0.0392(4) Uani 1 1 d . . . F17 F 1.48751(15) 0.03890(9) 0.69714(9) 0.0420(4) Uani 1 1 d . . . F18 F 1.52139(14) 0.04273(8) 0.83127(9) 0.0374(3) Uani 1 1 d . . . C1 C 0.7926(2) 0.13519(13) 0.73689(14) 0.0280(5) Uani 1 1 d . . . H1A H 0.7745 0.1220 0.6811 0.034 Uiso 1 1 calc R . . H1B H 0.8012 0.0915 0.7685 0.034 Uiso 1 1 calc R . . C2 C 0.8940(2) 0.25901(13) 0.72858(14) 0.0274(5) Uani 1 1 d . . . H2A H 0.9766 0.2832 0.7217 0.033 Uiso 1 1 calc R . . H2B H 0.8346 0.2614 0.6786 0.033 Uiso 1 1 calc R . . C3 C 0.9791(2) 0.17563(13) 0.84217(14) 0.0278(5) Uani 1 1 d . . . H3A H 1.0253 0.1303 0.8538 0.033 Uiso 1 1 calc R . . H3B H 1.0417 0.2146 0.8562 0.033 Uiso 1 1 calc R . . C4 C 0.9221(2) 0.17980(13) 0.75238(14) 0.0282(5) Uani 1 1 d . . . C5 C 1.0215(3) 0.14827(16) 0.70120(17) 0.0419(7) Uani 1 1 d . . . H5A H 1.0428 0.0993 0.7183 0.050 Uiso 1 1 d R . . H5B H 0.9796 0.1464 0.6462 0.050 Uiso 1 1 d R . . C6 C 0.5813(2) 0.19576(13) 0.70975(13) 0.0274(5) Uani 1 1 d . . . H6 H 0.5607 0.1717 0.6615 0.033 Uiso 1 1 calc R . . C7 C 0.4985(2) 0.25362(13) 0.73335(13) 0.0257(5) Uani 1 1 d . . . C8 C 0.3797(2) 0.27534(14) 0.69065(14) 0.0317(5) Uani 1 1 d . . . H8 H 0.3457 0.2520 0.6436 0.038 Uiso 1 1 calc R . . C9 C 0.3114(2) 0.33255(14) 0.71880(14) 0.0327(6) Uani 1 1 d . . . H9 H 0.2302 0.3478 0.6915 0.039 Uiso 1 1 calc R . . C10 C 0.3661(2) 0.36627(14) 0.78806(14) 0.0302(5) Uani 1 1 d . . . H10 H 0.3224 0.4049 0.8081 0.036 Uiso 1 1 calc R . . C11 C 0.4869(2) 0.34222(13) 0.82759(14) 0.0268(5) Uani 1 1 d . . . H11 H 0.5234 0.3655 0.8741 0.032 Uiso 1 1 calc R . . C12 C 0.8674(2) 0.35556(12) 0.82020(13) 0.0252(5) Uani 1 1 d . . . H12 H 0.9204 0.3866 0.7949 0.030 Uiso 1 1 calc R . . C13 C 0.8197(2) 0.37432(12) 0.89499(13) 0.0241(5) Uani 1 1 d . . . C14 C 0.8444(2) 0.43875(13) 0.93465(14) 0.0287(5) Uani 1 1 d . . . H14 H 0.8868 0.4763 0.9118 0.034 Uiso 1 1 calc R . . C15 C 0.8046(2) 0.44650(14) 1.00941(14) 0.0326(5) Uani 1 1 d . . . H15 H 0.8201 0.4893 1.0376 0.039 Uiso 1 1 calc R . . C16 C 0.7416(2) 0.38961(14) 1.04118(14) 0.0316(5) Uani 1 1 d . . . H16 H 0.7155 0.3936 1.0916 0.038 Uiso 1 1 calc R . . C17 C 0.7175(2) 0.32678(13) 0.99800(13) 0.0262(5) Uani 1 1 d . . . H17 H 0.6736 0.2891 1.0197 0.031 Uiso 1 1 calc R . . C18 C 0.8472(2) 0.13683(12) 0.94252(13) 0.0249(5) Uani 1 1 d . . . H18 H 0.9144 0.1063 0.9657 0.030 Uiso 1 1 calc R . . C19 C 0.7141(2) 0.13666(12) 0.96644(13) 0.0238(5) Uani 1 1 d . . . C20 C 0.6737(2) 0.09144(13) 1.02327(13) 0.0278(5) Uani 1 1 d . . . H20 H 0.7339 0.0604 1.0524 0.033 Uiso 1 1 calc R . . C21 C 0.5403(2) 0.09349(13) 1.03595(14) 0.0290(5) Uani 1 1 d . . . H21 H 0.5102 0.0641 1.0742 0.035 Uiso 1 1 calc R . . C22 C 0.4537(2) 0.13966(13) 0.99102(13) 0.0275(5) Uani 1 1 d . . . H22 H 0.3645 0.1417 0.9988 0.033 Uiso 1 1 calc R . . C23 C 0.5004(2) 0.18306(12) 0.93423(13) 0.0248(5) Uani 1 1 d . . . H23 H 0.4412 0.2138 0.9040 0.030 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 Co 0.02205(16) 0.01993(16) 0.02006(15) 0.00020(11) 0.00396(12) 0.00066(11) P1 0.0305(3) 0.0275(3) 0.0255(3) 0.0001(2) 0.0019(2) -0.0008(3) P2 0.0292(3) 0.0290(4) 0.0297(3) -0.0007(2) 0.0069(3) 0.0017(2) P3 0.0269(3) 0.0252(3) 0.0272(3) 0.0035(2) 0.0035(3) 0.0000(2) O1A 0.0266(12) 0.0352(14) 0.0461(15) -0.0045(10) 0.0092(10) 0.0009(10) O1B 0.033(4) 0.043(5) 0.022(4) 0.003(3) 0.014(3) 0.007(3) N1 0.0287(10) 0.0223(10) 0.0230(9) 0.0010(7) 0.0058(8) 0.0011(8) N2 0.0253(9) 0.0241(10) 0.0240(9) 0.0021(8) 0.0045(8) 0.0044(8) N3 0.0226(9) 0.0234(10) 0.0217(9) -0.0017(7) 0.0028(7) 0.0002(7) N4 0.0250(9) 0.0241(10) 0.0209(9) 0.0037(7) 0.0057(8) 0.0002(8) N5 0.0215(9) 0.0226(10) 0.0235(9) 0.0015(7) 0.0020(7) 0.0022(7) N6 0.0248(9) 0.0205(10) 0.0204(9) -0.0018(7) 0.0020(7) 0.0012(7) F1 0.0381(8) 0.0390(9) 0.0272(7) -0.0064(6) 0.0039(6) -0.0052(6) F2 0.0351(8) 0.0453(9) 0.0437(8) 0.0019(7) 0.0014(7) 0.0105(7) F3 0.0579(9) 0.0307(8) 0.0293(7) 0.0035(6) 0.0094(7) -0.0016(7) F4 0.0317(7) 0.0352(8) 0.0416(8) -0.0014(6) 0.0077(6) 0.0007(6) F5 0.0322(7) 0.0381(9) 0.0398(8) 0.0090(7) 0.0056(6) -0.0037(6) F6 0.0485(9) 0.0374(9) 0.0354(8) -0.0076(7) -0.0058(7) -0.0039(7) F7 0.0944(14) 0.0246(9) 0.0553(10) -0.0006(7) 0.0091(10) 0.0057(9) F8 0.0495(9) 0.0706(12) 0.0327(8) -0.0140(8) 0.0153(7) -0.0161(8) F9 0.0373(8) 0.0628(11) 0.0418(9) -0.0125(8) 0.0111(7) -0.0154(8) F10 0.0437(9) 0.0822(14) 0.0283(8) 0.0064(8) 0.0048(7) 0.0001(9) F11 0.0328(9) 0.1260(19) 0.0484(10) 0.0058(11) 0.0029(8) -0.0200(10) F12 0.0987(16) 0.0413(12) 0.1182(18) 0.0171(12) 0.0484(14) 0.0344(11) F13 0.0389(8) 0.0382(9) 0.0440(9) 0.0147(7) -0.0112(7) -0.0082(7) F14 0.0328(7) 0.0253(8) 0.0356(7) -0.0005(6) 0.0037(6) 0.0018(6) F15 0.0479(9) 0.0363(9) 0.0447(9) 0.0058(7) 0.0234(7) 0.0037(7) F16 0.0351(8) 0.0254(8) 0.0567(9) 0.0084(7) 0.0053(7) 0.0016(6) F17 0.0491(9) 0.0435(9) 0.0374(8) -0.0014(7) 0.0198(7) -0.0096(7) F18 0.0379(8) 0.0315(8) 0.0393(8) -0.0030(6) -0.0079(7) 0.0011(6) C1 0.0332(12) 0.0256(13) 0.0258(11) -0.0012(9) 0.0062(10) 0.0054(10) C2 0.0301(12) 0.0279(13) 0.0260(11) 0.0021(9) 0.0101(10) 0.0034(10) C3 0.0242(11) 0.0261(12) 0.0337(13) -0.0006(10) 0.0067(10) 0.0036(9) C4 0.0310(12) 0.0270(13) 0.0281(12) -0.0003(9) 0.0098(10) 0.0043(10) C5 0.0456(16) 0.0404(16) 0.0441(15) 0.0052(12) 0.0221(13) 0.0132(13) C6 0.0295(12) 0.0292(13) 0.0235(11) -0.0016(9) 0.0038(10) -0.0016(10) C7 0.0273(12) 0.0284(13) 0.0222(11) 0.0031(9) 0.0066(9) -0.0011(9) C8 0.0300(12) 0.0387(15) 0.0254(11) 0.0017(10) -0.0002(10) 0.0004(11) C9 0.0262(12) 0.0407(15) 0.0313(13) 0.0103(11) 0.0036(10) 0.0063(11) C10 0.0298(12) 0.0292(13) 0.0330(12) 0.0063(10) 0.0091(10) 0.0062(10) C11 0.0276(11) 0.0278(13) 0.0256(11) 0.0015(9) 0.0053(9) 0.0020(9) C12 0.0241(11) 0.0252(12) 0.0261(11) 0.0049(9) 0.0028(9) 0.0002(9) C13 0.0240(11) 0.0239(12) 0.0240(11) 0.0021(9) 0.0016(9) 0.0012(9) C14 0.0303(12) 0.0262(13) 0.0293(12) 0.0013(10) 0.0034(10) -0.0022(10) C15 0.0414(14) 0.0254(13) 0.0300(12) -0.0046(10) 0.0019(11) -0.0014(10) C16 0.0408(14) 0.0310(14) 0.0236(11) -0.0030(10) 0.0063(10) -0.0012(11) C17 0.0304(12) 0.0256(12) 0.0231(11) 0.0013(9) 0.0055(9) 0.0000(10) C18 0.0257(11) 0.0242(12) 0.0239(11) -0.0016(9) -0.0001(9) 0.0020(9) C19 0.0278(11) 0.0220(12) 0.0211(10) -0.0011(9) 0.0018(9) 0.0004(9) C20 0.0326(12) 0.0260(12) 0.0239(11) 0.0029(9) 0.0008(10) 0.0019(10) C21 0.0355(13) 0.0262(13) 0.0262(11) 0.0037(9) 0.0073(10) -0.0023(10) C22 0.0279(11) 0.0289(13) 0.0271(11) 0.0009(10) 0.0087(10) -0.0008(10) C23 0.0248(11) 0.0241(12) 0.0254(11) -0.0005(9) 0.0028(9) 0.0008(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 Co N2 1.8987(19) . ? Co N1 1.8998(19) . ? Co N3 1.9011(18) . ? Co N5 1.9403(19) . ? Co N6 1.9445(18) . ? Co N4 1.9512(18) . ? P1 F6 1.5968(15) . ? P1 F1 1.5981(15) . ? P1 F5 1.6014(15) . ? P1 F2 1.6016(15) . ? P1 F4 1.6025(15) . ? P1 F3 1.6099(15) . ? P2 F7 1.5744(17) . ? P2 F11 1.5819(17) . ? P2 F12 1.592(2) . ? P2 F10 1.5944(16) . ? P2 F9 1.5951(15) . ? P2 F8 1.5979(16) . ? P3 F18 1.5844(15) . ? P3 F15 1.5886(15) . ? P3 F14 1.5995(15) . ? P3 F13 1.6025(15) . ? P3 F17 1.6025(15) . ? P3 F16 1.6215(15) . ? O1A C5 1.345(4) . ? O1A H1 0.9765 . ? O1B C5 1.361(7) . ? N1 C6 1.278(3) . ? N1 C1 1.463(3) . ? N2 C12 1.270(3) . ? N2 C2 1.466(3) . ? N3 C18 1.276(3) . ? N3 C3 1.471(3) . ? N4 C11 1.332(3) . ? N4 C7 1.356(3) . ? N5 C17 1.340(3) . ? N5 C13 1.363(3) . ? N6 C23 1.339(3) . ? N6 C19 1.362(3) . ? C1 C4 1.542(3) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C4 1.542(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.553(3) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.530(3) . ? C5 H5A 0.9699 . ? C5 H5B 0.9701 . ? C6 C7 1.452(3) . ? C6 H6 0.9300 . ? C7 C8 1.376(3) . ? C8 C9 1.387(4) . ? C8 H8 0.9300 . ? C9 C10 1.378(4) . ? C9 H9 0.9300 . ? C10 C11 1.384(3) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 C13 1.458(3) . ? C12 H12 0.9300 . ? C13 C14 1.378(3) . ? C14 C15 1.387(3) . ? C14 H14 0.9300 . ? C15 C16 1.380(4) . ? C15 H15 0.9300 . ? C16 C17 1.381(3) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 C19 1.457(3) . ? C18 H18 0.9300 . ? C19 C20 1.381(3) . ? C20 C21 1.395(3) . ? C20 H20 0.9300 . ? C21 C22 1.378(3) . ? C21 H21 0.9300 . ? C22 C23 1.386(3) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? 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 N2 Co N1 86.98(8) . . ? N2 Co N3 88.12(8) . . ? N1 Co N3 88.49(8) . . ? N2 Co N5 82.62(8) . . ? N1 Co N5 167.83(8) . . ? N3 Co N5 97.43(8) . . ? N2 Co N6 169.84(8) . . ? N1 Co N6 97.30(8) . . ? N3 Co N6 82.81(8) . . ? N5 Co N6 93.99(7) . . ? N2 Co N4 95.74(8) . . ? N1 Co N4 82.94(8) . . ? N3 Co N4 170.40(8) . . ? N5 Co N4 91.79(8) . . ? N6 Co N4 93.93(8) . . ? F6 P1 F1 179.46(9) . . ? F6 P1 F5 90.43(8) . . ? F1 P1 F5 90.02(8) . . ? F6 P1 F2 89.88(9) . . ? F1 P1 F2 89.82(8) . . ? F5 P1 F2 90.05(8) . . ? F6 P1 F4 90.10(8) . . ? F1 P1 F4 90.19(8) . . ? F5 P1 F4 90.30(8) . . ? F2 P1 F4 179.66(10) . . ? F6 P1 F3 89.76(8) . . ? F1 P1 F3 89.80(8) . . ? F5 P1 F3 179.69(9) . . ? F2 P1 F3 90.19(8) . . ? F4 P1 F3 89.46(8) . . ? F7 P2 F11 91.43(12) . . ? F7 P2 F12 178.48(13) . . ? F11 P2 F12 90.08(13) . . ? F7 P2 F10 90.09(10) . . ? F11 P2 F10 90.12(9) . . ? F12 P2 F10 90.07(12) . . ? F7 P2 F9 90.05(11) . . ? F11 P2 F9 178.52(12) . . ? F12 P2 F9 88.44(12) . . ? F10 P2 F9 89.97(9) . . ? F7 P2 F8 89.78(10) . . ? F11 P2 F8 89.93(9) . . ? F12 P2 F8 90.05(12) . . ? F10 P2 F8 179.87(12) . . ? F9 P2 F8 89.99(8) . . ? F18 P3 F15 90.79(9) . . ? F18 P3 F14 90.98(8) . . ? F15 P3 F14 90.23(8) . . ? F18 P3 F13 178.58(9) . . ? F15 P3 F13 89.58(9) . . ? F14 P3 F13 90.40(8) . . ? F18 P3 F17 89.91(9) . . ? F15 P3 F17 179.14(10) . . ? F14 P3 F17 90.26(8) . . ? F13 P3 F17 89.72(9) . . ? F18 P3 F16 89.47(8) . . ? F15 P3 F16 89.71(8) . . ? F14 P3 F16 179.55(9) . . ? F13 P3 F16 89.15(8) . . ? F17 P3 F16 89.79(8) . . ? C5 O1A H1 108.2 . . ? C6 N1 C1 122.40(19) . . ? C6 N1 Co 115.32(16) . . ? C1 N1 Co 119.25(14) . . ? C12 N2 C2 123.31(19) . . ? C12 N2 Co 115.84(15) . . ? C2 N2 Co 119.79(15) . . ? C18 N3 C3 122.36(19) . . ? C18 N3 Co 115.76(15) . . ? C3 N3 Co 120.04(14) . . ? C11 N4 C7 118.14(19) . . ? C11 N4 Co 129.54(16) . . ? C7 N4 Co 112.24(15) . . ? C17 N5 C13 118.2(2) . . ? C17 N5 Co 129.42(16) . . ? C13 N5 Co 112.06(14) . . ? C23 N6 C19 118.54(19) . . ? C23 N6 Co 129.03(15) . . ? C19 N6 Co 112.36(14) . . ? N1 C1 C4 107.56(19) . . ? N1 C1 H1A 110.2 . . ? C4 C1 H1A 110.2 . . ? N1 C1 H1B 110.2 . . ? C4 C1 H1B 110.2 . . ? H1A C1 H1B 108.5 . . ? N2 C2 C4 108.38(18) . . ? N2 C2 H2A 110.0 . . ? C4 C2 H2A 110.0 . . ? N2 C2 H2B 110.0 . . ? C4 C2 H2B 110.0 . . ? H2A C2 H2B 108.4 . . ? N3 C3 C4 107.37(18) . . ? N3 C3 H3A 110.2 . . ? C4 C3 H3A 110.2 . . ? N3 C3 H3B 110.2 . . ? C4 C3 H3B 110.2 . . ? H3A C3 H3B 108.5 . . ? C5 C4 C2 109.2(2) . . ? C5 C4 C1 107.8(2) . . ? C2 C4 C1 110.24(19) . . ? C5 C4 C3 110.5(2) . . ? C2 C4 C3 109.53(19) . . ? C1 C4 C3 109.46(19) . . ? O1A C5 O1B 64.4(3) . . ? O1A C5 C4 113.5(2) . . ? O1B C5 C4 117.8(4) . . ? O1A C5 H5A 109.1 . . ? O1B C5 H5A 131.2 . . ? C4 C5 H5A 109.0 . . ? O1A C5 H5B 108.5 . . ? O1B C5 H5B 45.3 . . ? C4 C5 H5B 108.8 . . ? H5A C5 H5B 107.7 . . ? N1 C6 C7 116.2(2) . . ? N1 C6 H6 121.9 . . ? C7 C6 H6 121.9 . . ? N4 C7 C8 122.4(2) . . ? N4 C7 C6 113.0(2) . . ? C8 C7 C6 124.6(2) . . ? C7 C8 C9 119.0(2) . . ? C7 C8 H8 120.5 . . ? C9 C8 H8 120.5 . . ? C10 C9 C8 118.7(2) . . ? C10 C9 H9 120.7 . . ? C8 C9 H9 120.7 . . ? C9 C10 C11 119.4(2) . . ? C9 C10 H10 120.3 . . ? C11 C10 H10 120.3 . . ? N4 C11 C10 122.4(2) . . ? N4 C11 H11 118.8 . . ? C10 C11 H11 118.8 . . ? N2 C12 C13 115.7(2) . . ? N2 C12 H12 122.2 . . ? C13 C12 H12 122.2 . . ? N5 C13 C14 122.5(2) . . ? N5 C13 C12 112.4(2) . . ? C14 C13 C12 124.8(2) . . ? C13 C14 C15 118.6(2) . . ? C13 C14 H14 120.7 . . ? C15 C14 H14 120.7 . . ? C16 C15 C14 118.9(2) . . ? C16 C15 H15 120.6 . . ? C14 C15 H15 120.6 . . ? C15 C16 C17 119.9(2) . . ? C15 C16 H16 120.1 . . ? C17 C16 H16 120.1 . . ? N5 C17 C16 121.9(2) . . ? N5 C17 H17 119.1 . . ? C16 C17 H17 119.1 . . ? N3 C18 C19 115.8(2) . . ? N3 C18 H18 122.1 . . ? C19 C18 H18 122.1 . . ? N6 C19 C20 122.4(2) . . ? N6 C19 C18 112.76(19) . . ? C20 C19 C18 124.6(2) . . ? C19 C20 C21 118.4(2) . . ? C19 C20 H20 120.8 . . ? C21 C20 H20 120.8 . . ? C22 C21 C20 119.1(2) . . ? C22 C21 H21 120.4 . . ? C20 C21 H21 120.4 . . ? C21 C22 C23 119.6(2) . . ? C21 C22 H22 120.2 . . ? C23 C22 H22 120.2 . . ? N6 C23 C22 121.9(2) . . ? N6 C23 H23 119.1 . . ? C22 C23 H23 119.1 . . ? 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 O1A H1 F16 0.98 1.81 2.769(3) 165.7 . data_1_0 _database_code_depnum_ccdc_archive 'CCDC 845930' #TrackingRef 'combined_final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H24 Co N6 O1, 3(Cl O4), (C H4 O)' _chemical_formula_sum 'C24 H28 Cl3 Co N6 O14' _chemical_formula_weight 789.80 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 trigonal _symmetry_space_group_name_H-M R-3 _symmetry_space_group_name_Hall '-R 3' _symmetry_Inl_Tables_number 148 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 31.919(4) _cell_length_b 31.919 _cell_length_c 18.413(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 16246(3) _cell_formula_units_Z 18 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 8293 _cell_measurement_theta_min 2.75 _cell_measurement_theta_max 23.8 _exptl_crystal_description mulit-face _exptl_crystal_colour red _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.453 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 7272 _exptl_absorpt_coefficient_mu 0.766 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.831299 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2007)' _exptl_special_details ; The crystal was coated in Exxon Paratone N hydrocarbon oil and mounted on a thin mohair fibre attached to a copper pin. Upon mounting on the diffractometer, the crystal was quenched to 150(K) under a cold nitrogen gas stream supplied by an Oxford Cryosystems Cryostream and data were collected at this temperature. ; loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons 1 0.000 0.000 -0.005 1128.7 602.5 2 0.333 0.667 0.123 1124.9 601.9 3 0.667 0.333 0.790 1124.9 601.7 _platon_squeeze_details ; ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type APEXII-FR591 _diffrn_measurement_method \w+\f _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 196821 _diffrn_reflns_av_R_equivalents 0.0494 _diffrn_reflns_av_sigmaI/netI 0.0241 _diffrn_reflns_limit_h_min -42 _diffrn_reflns_limit_h_max 42 _diffrn_reflns_limit_k_min -42 _diffrn_reflns_limit_k_max 42 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.28 _diffrn_reflns_theta_max 28.56 _reflns_number_total 9206 _reflns_number_gt 6117 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX (Bruker-Nonius, 2003)' _computing_cell_refinement 'SAINT (Bruker-Nonius, 2003)' _computing_data_reduction 'SAINT (Bruker-Nonius, 2003), XPREP (Bruker-Nonius, 2003)' _computing_structure_solution 'SIR97 (Altomare, et. al. 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ;ORTEP-3 (Farrugia, 1997) WINGX-32 (Farrugia, 1999) ; _computing_publication_material 'enCIFer 1.1 (CCDC, 2005)' _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^)+(0.2000P)^2^+0.0000P] 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 9206 _refine_ls_number_parameters 421 _refine_ls_number_restraints 31 _refine_ls_R_factor_all 0.1240 _refine_ls_R_factor_gt 0.0958 _refine_ls_wR_factor_ref 0.3204 _refine_ls_wR_factor_gt 0.2972 _refine_ls_goodness_of_fit_ref 1.200 _refine_ls_restrained_S_all 1.200 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.5767(6) 0.1690(6) 0.3990(7) 0.074(2) Uani 0.50 1 d P A 1 H1A H 0.5611 0.1875 0.4150 0.089 Uiso 0.50 1 calc PR A 1 H1B H 0.5886 0.1595 0.4420 0.089 Uiso 0.50 1 calc PR A 1 C1A C 0.5803(6) 0.1650(6) 0.3670(7) 0.074(2) Uani 0.25 1 d P A 2 H1A1 H 0.6021 0.1772 0.3244 0.089 Uiso 0.25 1 calc PR A 2 H1A2 H 0.5979 0.1605 0.4077 0.089 Uiso 0.25 1 calc PR A 2 C1B C 0.5803(6) 0.1650(6) 0.3670(7) 0.074(2) Uani 0.25 1 d P A 3 H1B1 H 0.5954 0.1604 0.4109 0.089 Uiso 0.25 1 calc PR A 3 H1B2 H 0.5701 0.1889 0.3791 0.089 Uiso 0.25 1 calc PR A 3 C2 C 0.53892(17) 0.1209(2) 0.3500(4) 0.0935(19) Uani 1 1 d . . . C3 C 0.50940(19) 0.1333(2) 0.2951(4) 0.096(2) Uani 1 1 d . A . H3A H 0.4861 0.1397 0.3213 0.115 Uiso 1 1 calc R . . H3B H 0.5314 0.1624 0.2665 0.115 Uiso 1 1 calc R . . C4 C 0.48624(19) 0.0953(3) 0.1796(4) 0.097(2) Uani 1 1 d . A . H4 H 0.4991 0.1262 0.1574 0.116 Uiso 1 1 calc R . . C5 C 0.46900(19) 0.0503(3) 0.1385(3) 0.093(2) Uani 1 1 d . A . C6 C 0.4664(3) 0.0444(5) 0.0617(4) 0.145(4) Uani 1 1 d . . . H6 H 0.4745 0.0714 0.0313 0.174 Uiso 1 1 calc R . . C7 C 0.4520(3) -0.0013(5) 0.0302(4) 0.132(4) Uani 1 1 d . . . H7 H 0.4515 -0.0045 -0.0211 0.158 Uiso 1 1 calc R . . C8 C 0.4386(2) -0.0410(3) 0.0740(3) 0.103(2) Uani 1 1 d . . . H8 H 0.4270 -0.0724 0.0542 0.123 Uiso 1 1 calc R . . C9 C 0.44285(19) -0.0325(3) 0.1512(2) 0.0803(16) Uani 1 1 d . A . H9 H 0.4361 -0.0589 0.1823 0.096 Uiso 1 1 calc R . . C10 C 0.56096(19) 0.0940(2) 0.3084(4) 0.102(2) Uani 1 1 d . A . H10A H 0.5724 0.1088 0.2599 0.122 Uiso 1 1 calc R . . H10B H 0.5889 0.0966 0.3356 0.122 Uiso 1 1 calc R . . C11 C 0.52931(17) 0.00870(19) 0.3215(3) 0.0687(12) Uani 1 1 d . A . H11 H 0.5605 0.0133 0.3322 0.082 Uiso 1 1 calc R . . C12 C 0.48606(17) -0.03883(17) 0.3287(2) 0.0615(10) Uani 1 1 d . A . C13 C 0.4848(2) -0.0805(2) 0.3511(3) 0.0773(14) Uani 1 1 d . . . H13 H 0.5140 -0.0803 0.3620 0.093 Uiso 1 1 calc R . . C14 C 0.4415(2) -0.1222(2) 0.3577(3) 0.0851(15) Uani 1 1 d . . . H14 H 0.4403 -0.1516 0.3711 0.102 Uiso 1 1 calc R . . C15 C 0.3990(2) -0.1211(2) 0.3446(3) 0.0858(15) Uani 1 1 d . . . H15 H 0.3684 -0.1496 0.3503 0.103 Uiso 1 1 calc R . . C16 C 0.40170(18) -0.07841(17) 0.3233(2) 0.0640(10) Uani 1 1 d . A . H16 H 0.3727 -0.0779 0.3135 0.077 Uiso 1 1 calc R . . C17 C 0.50577(18) 0.08800(19) 0.4100(4) 0.0835(15) Uani 1 1 d . A . H17A H 0.5209 0.0712 0.4343 0.100 Uiso 1 1 calc R . . H17B H 0.5005 0.1075 0.4468 0.100 Uiso 1 1 calc R . . C18 C 0.41915(18) 0.04960(18) 0.3978(2) 0.0668(11) Uani 1 1 d . A . H18 H 0.4164 0.0638 0.4416 0.080 Uiso 1 1 calc R . . C19 C 0.37891(15) 0.02381(16) 0.3509(2) 0.0576(9) Uani 1 1 d . A . C20 C 0.33250(16) 0.01603(17) 0.3647(2) 0.0594(10) Uani 1 1 d . . . H20 H 0.3256 0.0267 0.4089 0.071 Uiso 1 1 calc R . . C21 C 0.29681(16) -0.00742(17) 0.3130(2) 0.0631(11) Uani 1 1 d . . . H21 H 0.2650 -0.0130 0.3211 0.076 Uiso 1 1 calc R . . C22 C 0.30794(15) -0.02260(16) 0.2495(2) 0.0604(10) Uani 1 1 d . . . H22 H 0.2837 -0.0396 0.2139 0.072 Uiso 1 1 calc R . . C23 C 0.35507(14) -0.01281(16) 0.2379(2) 0.0557(9) Uani 1 1 d . A . H23 H 0.3626 -0.0226 0.1935 0.067 Uiso 1 1 calc R . . N1 N 0.48244(14) 0.08905(18) 0.2448(3) 0.0826(14) Uani 1 1 d . . . N2 N 0.45565(14) 0.00979(19) 0.1810(2) 0.0751(12) Uani 1 1 d . . . N3 N 0.52402(13) 0.04362(15) 0.3006(2) 0.0691(10) Uani 1 1 d . . . N4 N 0.44449(13) -0.03746(13) 0.31605(18) 0.0584(8) Uani 1 1 d . . . N5 N 0.46009(14) 0.05295(14) 0.3784(2) 0.0643(9) Uani 1 1 d . . . N6 N 0.39020(12) 0.01002(12) 0.28735(17) 0.0532(7) Uani 1 1 d . . . O1 O 0.6160(4) 0.1968(4) 0.3470(8) 0.119(3) Uani 0.50 1 d P A 1 H1 H 0.6221 0.1782 0.3247 0.179 Uiso 0.50 1 d PR A 1 O1A O 0.5659(7) 0.1984(7) 0.3867(12) 0.119(3) Uani 0.25 1 d P A 2 H1A3 H 0.5364 0.1841 0.3926 0.179 Uiso 0.25 1 d PR A 2 O1B O 0.6183(9) 0.1860(8) 0.3068(17) 0.119(3) Uani 0.25 1 d P A 3 H1B3 H 0.6459 0.1975 0.3225 0.179 Uiso 0.25 1 d PR A 3 O2 O 0.3261(3) 0.0849(3) 0.2020(4) 0.0822(10) Uani 0.50 1 d P B 1 O3 O 0.38577(12) 0.08091(12) 0.12914(17) 0.0687(8) Uani 0.50 1 d P B 1 O4 O 0.3998(5) 0.1107(4) 0.2511(8) 0.0822(10) Uani 0.50 1 d P B 1 O5 O 0.3908(6) 0.1557(7) 0.1553(10) 0.0822(10) Uani 0.25 1 d P B 1 O5A O 0.3744(6) 0.1479(8) 0.1503(11) 0.0822(10) Uani 0.25 1 d P B 1 Cl1 Cl 0.37638(11) 0.1093(2) 0.1832(4) 0.0510(7) Uani 0.50 1 d P B 1 O3A O 0.38577(12) 0.08091(12) 0.12914(17) 0.0687(8) Uani 0.50 1 d P C 2 Cl1A Cl 0.39257(11) 0.1165(2) 0.1803(4) 0.0510(7) Uani 0.50 1 d P C 2 O5B O 0.4400(3) 0.1598(3) 0.1705(4) 0.0822(10) Uani 0.50 1 d P C 2 O4A O 0.3906(5) 0.0978(4) 0.2512(8) 0.0822(10) Uani 0.50 1 d P C 2 O2A O 0.3534(3) 0.1280(3) 0.1740(4) 0.0822(10) Uani 0.50 1 d P C 2 O6 O 0.4766(2) -0.1165(3) 0.1851(6) 0.1106(9) Uani 0.75 1 d PD D 1 O7 O 0.5421(2) -0.0391(2) 0.1780(3) 0.1106(9) Uani 0.75 1 d PD D 1 O8 O 0.5328(4) -0.0977(3) 0.0894(3) 0.1106(9) Uani 0.75 1 d PD D 1 O9 O 0.5591(2) -0.0964(3) 0.2072(3) 0.1106(9) Uani 0.75 1 d PD D 1 Cl2 Cl 0.52659(8) -0.08907(6) 0.16369(10) 0.0657(5) Uani 0.75 1 d PD D 1 O6A O 0.4750(5) -0.1129(8) 0.1825(15) 0.1106(9) Uani 0.25 1 d PD E 2 Cl2A Cl 0.5204(3) -0.1089(2) 0.1618(4) 0.0657(5) Uani 0.25 1 d PD E 2 O7A O 0.5565(5) -0.0714(6) 0.2074(9) 0.1106(9) Uani 0.25 1 d PD E 2 O8A O 0.5324(10) -0.0854(9) 0.0924(8) 0.1106(9) Uani 0.25 1 d PD E 2 O9A O 0.5124(6) -0.1574(4) 0.1642(10) 0.1106(9) Uani 0.25 1 d PD E 2 O13 O 0.6478(4) 0.1265(4) 0.0454(7) 0.1271(13) Uani 0.50 1 d P F 1 O12 O 0.6506(4) 0.1582(4) 0.1653(7) 0.1271(13) Uani 0.50 1 d P F 1 Cl3 Cl 0.62553(16) 0.12256(16) 0.1103(2) 0.0723(8) Uani 0.50 1 d P F 1 O10 O 0.5803(4) 0.1134(4) 0.1006(7) 0.1271(13) Uani 0.50 1 d P F 1 O11 O 0.6288(4) 0.0868(5) 0.1526(8) 0.1271(13) Uani 0.50 1 d P F 1 O13A O 0.5833(4) 0.0706(4) 0.0825(7) 0.1271(13) Uani 0.50 1 d P G 2 O11A O 0.5966(4) 0.1379(4) 0.1498(7) 0.1271(13) Uani 0.50 1 d P G 2 O12A O 0.6615(4) 0.1229(4) 0.1129(7) 0.1271(13) Uani 0.50 1 d P G 2 O10A O 0.6057(4) 0.0697(5) 0.1862(7) 0.1271(13) Uani 0.50 1 d P G 2 Cl3A Cl 0.61502(16) 0.10527(16) 0.1329(2) 0.0723(8) Uani 0.50 1 d P G 2 Co1 Co 0.45830(2) 0.02681(2) 0.28419(3) 0.0601(2) Uani 1 1 d . A . 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 C1 0.077(4) 0.070(4) 0.068(8) 0.001(7) 0.004(7) 0.031(3) C1A 0.077(4) 0.070(4) 0.068(8) 0.001(7) 0.004(7) 0.031(3) C1B 0.077(4) 0.070(4) 0.068(8) 0.001(7) 0.004(7) 0.031(3) C2 0.053(2) 0.076(3) 0.158(6) 0.027(3) -0.012(3) 0.037(2) C3 0.060(3) 0.092(4) 0.143(6) 0.038(4) -0.009(3) 0.044(3) C4 0.061(3) 0.133(5) 0.117(5) 0.064(4) 0.033(3) 0.064(3) C5 0.064(3) 0.171(6) 0.073(3) 0.066(4) 0.029(2) 0.079(4) C6 0.089(4) 0.307(12) 0.090(5) 0.118(7) 0.054(4) 0.137(7) C7 0.113(5) 0.282(12) 0.061(4) 0.055(6) 0.033(4) 0.144(8) C8 0.094(4) 0.201(7) 0.055(3) 0.007(4) 0.008(3) 0.104(5) C9 0.076(3) 0.149(5) 0.047(2) 0.008(3) 0.008(2) 0.080(4) C10 0.059(3) 0.113(4) 0.141(6) 0.051(4) 0.001(3) 0.049(3) C11 0.069(3) 0.095(3) 0.066(3) 0.003(2) 0.002(2) 0.059(3) C12 0.082(3) 0.083(3) 0.0408(19) -0.0054(18) -0.0026(18) 0.057(3) C13 0.108(4) 0.091(4) 0.068(3) -0.007(2) -0.002(3) 0.077(3) C14 0.113(4) 0.074(3) 0.090(4) 0.003(3) 0.012(3) 0.062(3) C15 0.109(4) 0.077(3) 0.086(4) 0.001(3) 0.014(3) 0.057(3) C16 0.077(3) 0.074(3) 0.049(2) -0.0006(19) 0.0060(19) 0.044(2) C17 0.073(3) 0.075(3) 0.120(5) -0.007(3) -0.027(3) 0.050(3) C18 0.082(3) 0.078(3) 0.055(2) 0.007(2) 0.000(2) 0.052(3) C19 0.070(2) 0.073(2) 0.0439(19) 0.0143(17) 0.0055(17) 0.046(2) C20 0.069(2) 0.077(3) 0.046(2) 0.0183(18) 0.0199(18) 0.048(2) C21 0.060(2) 0.077(3) 0.062(2) 0.023(2) 0.0193(19) 0.041(2) C22 0.058(2) 0.076(3) 0.054(2) 0.0111(19) 0.0033(17) 0.039(2) C23 0.058(2) 0.073(2) 0.0434(19) 0.0068(17) 0.0062(16) 0.038(2) N1 0.057(2) 0.102(3) 0.095(3) 0.054(3) 0.012(2) 0.044(2) N2 0.065(2) 0.130(4) 0.054(2) 0.030(2) 0.0201(17) 0.067(2) N3 0.0548(19) 0.084(3) 0.079(3) 0.021(2) 0.0049(17) 0.043(2) N4 0.071(2) 0.079(2) 0.0443(17) 0.0015(15) 0.0038(14) 0.051(2) N5 0.071(2) 0.070(2) 0.068(2) 0.0099(17) -0.0013(17) 0.0465(19) N6 0.0597(18) 0.068(2) 0.0432(16) 0.0137(14) 0.0090(13) 0.0408(16) O1 0.094(5) 0.085(5) 0.177(12) -0.027(6) -0.023(6) 0.044(4) O1A 0.094(5) 0.085(5) 0.177(12) -0.027(6) -0.023(6) 0.044(4) O1B 0.094(5) 0.085(5) 0.177(12) -0.027(6) -0.023(6) 0.044(4) O2 0.097(3) 0.097(3) 0.0636(16) -0.0084(18) -0.0073(17) 0.056(3) O3 0.088(2) 0.0715(18) 0.0583(17) -0.0118(14) -0.0137(15) 0.0487(17) O4 0.097(3) 0.097(3) 0.0636(16) -0.0084(18) -0.0073(17) 0.056(3) O5 0.097(3) 0.097(3) 0.0636(16) -0.0084(18) -0.0073(17) 0.056(3) O5A 0.097(3) 0.097(3) 0.0636(16) -0.0084(18) -0.0073(17) 0.056(3) Cl1 0.054(2) 0.0551(17) 0.0467(7) 0.0008(9) -0.0059(19) 0.030(2) O3A 0.088(2) 0.0715(18) 0.0583(17) -0.0118(14) -0.0137(15) 0.0487(17) Cl1A 0.054(2) 0.0551(17) 0.0467(7) 0.0008(9) -0.0059(19) 0.030(2) O5B 0.097(3) 0.097(3) 0.0636(16) -0.0084(18) -0.0073(17) 0.056(3) O4A 0.097(3) 0.097(3) 0.0636(16) -0.0084(18) -0.0073(17) 0.056(3) O2A 0.097(3) 0.097(3) 0.0636(16) -0.0084(18) -0.0073(17) 0.056(3) O6 0.1044(17) 0.128(3) 0.0864(16) 0.0047(16) 0.0102(13) 0.0486(17) O7 0.1044(17) 0.128(3) 0.0864(16) 0.0047(16) 0.0102(13) 0.0486(17) O8 0.1044(17) 0.128(3) 0.0864(16) 0.0047(16) 0.0102(13) 0.0486(17) O9 0.1044(17) 0.128(3) 0.0864(16) 0.0047(16) 0.0102(13) 0.0486(17) Cl2 0.0739(9) 0.0809(13) 0.0501(6) 0.0014(10) 0.0068(6) 0.0446(12) O6A 0.1044(17) 0.128(3) 0.0864(16) 0.0047(16) 0.0102(13) 0.0486(17) Cl2A 0.0739(9) 0.0809(13) 0.0501(6) 0.0014(10) 0.0068(6) 0.0446(12) O7A 0.1044(17) 0.128(3) 0.0864(16) 0.0047(16) 0.0102(13) 0.0486(17) O8A 0.1044(17) 0.128(3) 0.0864(16) 0.0047(16) 0.0102(13) 0.0486(17) O9A 0.1044(17) 0.128(3) 0.0864(16) 0.0047(16) 0.0102(13) 0.0486(17) O13 0.103(3) 0.137(3) 0.158(4) -0.007(3) 0.008(2) 0.072(3) O12 0.103(3) 0.137(3) 0.158(4) -0.007(3) 0.008(2) 0.072(3) Cl3 0.0759(19) 0.102(3) 0.057(2) -0.0147(13) 0.0015(12) 0.058(2) O10 0.103(3) 0.137(3) 0.158(4) -0.007(3) 0.008(2) 0.072(3) O11 0.103(3) 0.137(3) 0.158(4) -0.007(3) 0.008(2) 0.072(3) O13A 0.103(3) 0.137(3) 0.158(4) -0.007(3) 0.008(2) 0.072(3) O11A 0.103(3) 0.137(3) 0.158(4) -0.007(3) 0.008(2) 0.072(3) O12A 0.103(3) 0.137(3) 0.158(4) -0.007(3) 0.008(2) 0.072(3) O10A 0.103(3) 0.137(3) 0.158(4) -0.007(3) 0.008(2) 0.072(3) Cl3A 0.0759(19) 0.102(3) 0.057(2) -0.0147(13) 0.0015(12) 0.058(2) Co1 0.0562(4) 0.0821(4) 0.0546(4) 0.0195(3) 0.0091(2) 0.0441(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 C1 O1 1.47(2) . ? C1 C2 1.666(17) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C1A C2 1.402(18) . ? C1A O1A 1.40(2) . ? C1A H1A1 0.9900 . ? C1A H1A2 0.9900 . ? C2 C17 1.528(9) . ? C2 C10 1.556(10) . ? C2 C3 1.561(7) . ? C3 N1 1.542(9) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 N1 1.213(7) . ? C4 C5 1.466(10) . ? C4 H4 0.9500 . ? C5 N2 1.384(7) . ? C5 C6 1.422(11) . ? C6 C7 1.414(15) . ? C6 H6 0.9500 . ? C7 C8 1.377(12) . ? C7 H7 0.9500 . ? C8 C9 1.440(7) . ? C8 H8 0.9500 . ? C9 N2 1.320(8) . ? C9 H9 0.9500 . ? C10 N3 1.450(7) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 N3 1.268(6) . ? C11 C12 1.460(7) . ? C11 H11 0.9500 . ? C12 N4 1.369(5) . ? C12 C13 1.374(7) . ? C13 C14 1.363(8) . ? C13 H13 0.9500 . ? C14 C15 1.394(8) . ? C14 H14 0.9500 . ? C15 C16 1.380(7) . ? C15 H15 0.9500 . ? C16 N4 1.344(6) . ? C16 H16 0.9500 . ? C17 N5 1.444(6) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 N5 1.307(6) . ? C18 C19 1.420(6) . ? C18 H18 0.9500 . ? C19 N6 1.361(5) . ? C19 C20 1.397(6) . ? C20 C21 1.383(7) . ? C20 H20 0.9500 . ? C21 C22 1.378(6) . ? C21 H21 0.9500 . ? C22 C23 1.391(5) . ? C22 H22 0.9500 . ? C23 N6 1.341(5) . ? C23 H23 0.9500 . ? N1 Co1 1.881(4) . ? N2 Co1 1.967(5) . ? N3 Co1 1.911(3) . ? N4 Co1 1.960(4) . ? N5 Co1 1.914(4) . ? N6 Co1 1.962(3) . ? O1 H1 0.8200 . ? O1 H1B3 1.0464 . ? O1A H1A3 0.8200 . ? O1B H1 0.4646 . ? O1B H1B3 0.8200 . ? O2 Cl1 1.433(9) . ? O3 Cl1 1.475(7) . ? O4 Cl1 1.445(16) . ? O5 Cl1 1.41(2) . ? O5A Cl1 1.40(2) . ? Cl1A O4A 1.421(16) . ? Cl1A O5B 1.464(9) . ? Cl1A O2A 1.473(9) . ? O6 Cl2 1.439(6) . ? O7 Cl2 1.439(6) . ? O8 Cl2 1.429(5) . ? O9 Cl2 1.421(5) . ? O6A Cl2A 1.440(7) . ? Cl2A O9A 1.436(7) . ? Cl2A O8A 1.434(8) . ? Cl2A O7A 1.444(7) . ? O13 Cl3 1.363(13) . ? O12 Cl3 1.432(13) . ? Cl3 O10 1.334(11) . ? Cl3 O11 1.429(15) . ? O13A Cl3A 1.410(13) . ? O11A Cl3A 1.464(11) . ? O12A Cl3A 1.348(12) . ? O10A Cl3A 1.415(14) . ? 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 C1 C2 102.1(9) . . ? O1 C1 H1A 111.3 . . ? C2 C1 H1A 111.3 . . ? O1 C1 H1B 111.3 . . ? C2 C1 H1B 111.3 . . ? H1A C1 H1B 109.2 . . ? C2 C1A O1A 108.7(14) . . ? C2 C1A H1A1 110.0 . . ? O1A C1A H1A1 110.0 . . ? C2 C1A H1A2 110.0 . . ? O1A C1A H1A2 110.0 . . ? H1A1 C1A H1A2 108.3 . . ? C2 C1A H1 116.8 . . ? O1A C1A H1 122.3 . . ? H1A1 C1A H1 22.0 . . ? H1A2 C1A H1 86.5 . . ? C1A C2 C17 120.6(8) . . ? C1A C2 C10 101.9(7) . . ? C17 C2 C10 109.1(4) . . ? C1A C2 C3 105.9(8) . . ? C17 C2 C3 110.1(4) . . ? C10 C2 C3 108.5(6) . . ? C1A C2 C1 21.4(7) . . ? C17 C2 C1 100.1(7) . . ? C10 C2 C1 117.1(7) . . ? C3 C2 C1 111.6(7) . . ? N1 C3 C2 106.7(4) . . ? N1 C3 H3A 110.4 . . ? C2 C3 H3A 110.4 . . ? N1 C3 H3B 110.4 . . ? C2 C3 H3B 110.4 . . ? H3A C3 H3B 108.6 . . ? N1 C4 C5 113.1(6) . . ? N1 C4 H4 123.4 . . ? C5 C4 H4 123.4 . . ? N2 C5 C6 117.9(9) . . ? N2 C5 C4 114.4(5) . . ? C6 C5 C4 127.7(7) . . ? C7 C6 C5 120.8(8) . . ? C7 C6 H6 119.6 . . ? C5 C6 H6 119.6 . . ? C8 C7 C6 119.9(7) . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C7 C8 C9 116.6(8) . . ? C7 C8 H8 121.7 . . ? C9 C8 H8 121.7 . . ? N2 C9 C8 123.7(6) . . ? N2 C9 H9 118.2 . . ? C8 C9 H9 118.2 . . ? N3 C10 C2 108.6(4) . . ? N3 C10 H10A 110.0 . . ? C2 C10 H10A 110.0 . . ? N3 C10 H10B 110.0 . . ? C2 C10 H10B 110.0 . . ? H10A C10 H10B 108.3 . . ? N3 C11 C12 118.0(4) . . ? N3 C11 H11 121.0 . . ? C12 C11 H11 121.0 . . ? N4 C12 C13 121.5(5) . . ? N4 C12 C11 112.3(4) . . ? C13 C12 C11 126.0(4) . . ? C14 C13 C12 119.7(5) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? C13 C14 C15 119.0(5) . . ? C13 C14 H14 120.5 . . ? C15 C14 H14 120.5 . . ? C16 C15 C14 119.5(6) . . ? C16 C15 H15 120.2 . . ? C14 C15 H15 120.2 . . ? N4 C16 C15 121.3(5) . . ? N4 C16 H16 119.3 . . ? C15 C16 H16 119.3 . . ? N5 C17 C2 108.9(5) . . ? N5 C17 H17A 109.9 . . ? C2 C17 H17A 109.9 . . ? N5 C17 H17B 109.9 . . ? C2 C17 H17B 109.9 . . ? H17A C17 H17B 108.3 . . ? N5 C18 C19 117.3(4) . . ? N5 C18 H18 121.3 . . ? C19 C18 H18 121.3 . . ? N6 C19 C20 121.8(4) . . ? N6 C19 C18 113.7(4) . . ? C20 C19 C18 124.3(4) . . ? C21 C20 C19 119.0(4) . . ? C21 C20 H20 120.5 . . ? C19 C20 H20 120.5 . . ? C20 C21 C22 119.1(4) . . ? C20 C21 H21 120.4 . . ? C22 C21 H21 120.4 . . ? C21 C22 C23 119.4(4) . . ? C21 C22 H22 120.3 . . ? C23 C22 H22 120.3 . . ? N6 C23 C22 122.3(4) . . ? N6 C23 H23 118.8 . . ? C22 C23 H23 118.8 . . ? C4 N1 C3 118.7(6) . . ? C4 N1 Co1 120.6(5) . . ? C3 N1 Co1 118.8(3) . . ? C9 N2 C5 120.9(5) . . ? C9 N2 Co1 129.3(3) . . ? C5 N2 Co1 109.8(5) . . ? C11 N3 C10 123.6(4) . . ? C11 N3 Co1 114.3(3) . . ? C10 N3 Co1 119.8(3) . . ? C16 N4 C12 118.8(4) . . ? C16 N4 Co1 129.4(3) . . ? C12 N4 Co1 111.7(3) . . ? C18 N5 C17 122.3(4) . . ? C18 N5 Co1 113.7(3) . . ? C17 N5 Co1 120.1(3) . . ? C23 N6 C19 118.3(3) . . ? C23 N6 Co1 129.7(3) . . ? C19 N6 Co1 111.9(3) . . ? C1 O1 H1 109.1 . . ? C1 O1 H1B3 141.8 . . ? H1 O1 H1B3 41.9 . . ? C1A O1A H1A3 109.1 . . ? H1 O1B H1B3 58.5 . . ? O5A Cl1 O5 19.0(10) . . ? O5A Cl1 O2 92.9(9) . . ? O5 Cl1 O2 110.3(9) . . ? O5A Cl1 O4 126.7(9) . . ? O5 Cl1 O4 113.1(9) . . ? O2 Cl1 O4 103.3(7) . . ? O5A Cl1 O3 111.1(10) . . ? O5 Cl1 O3 109.9(9) . . ? O2 Cl1 O3 110.2(5) . . ? O4 Cl1 O3 110.0(7) . . ? O4A Cl1A O5B 108.5(7) . . ? O4A Cl1A O2A 108.0(8) . . ? O5B Cl1A O2A 111.1(6) . . ? O9 Cl2 O8 108.9(5) . . ? O9 Cl2 O7 101.8(4) . . ? O8 Cl2 O7 112.7(4) . . ? O9 Cl2 O6 115.2(5) . . ? O8 Cl2 O6 111.4(5) . . ? O7 Cl2 O6 106.6(5) . . ? O9A Cl2A O8A 116.6(13) . . ? O9A Cl2A O6A 105.5(7) . . ? O8A Cl2A O6A 106.0(8) . . ? O9A Cl2A O7A 120.9(12) . . ? O8A Cl2A O7A 101.0(15) . . ? O6A Cl2A O7A 105.6(8) . . ? O10 Cl3 O13 111.0(8) . . ? O10 Cl3 O11 113.7(8) . . ? O13 Cl3 O11 108.0(7) . . ? O10 Cl3 O12 112.4(7) . . ? O13 Cl3 O12 119.3(7) . . ? O11 Cl3 O12 90.9(7) . . ? O12A Cl3A O13A 110.8(7) . . ? O12A Cl3A O10A 105.7(7) . . ? O13A Cl3A O10A 92.6(7) . . ? O12A Cl3A O11A 120.8(8) . . ? O13A Cl3A O11A 108.2(7) . . ? O10A Cl3A O11A 115.2(7) . . ? N1 Co1 N3 87.24(16) . . ? N1 Co1 N5 89.0(2) . . ? N3 Co1 N5 86.86(17) . . ? N1 Co1 N4 168.53(17) . . ? N3 Co1 N4 83.54(16) . . ? N5 Co1 N4 97.30(14) . . ? N1 Co1 N6 96.47(15) . . ? N3 Co1 N6 169.21(15) . . ? N5 Co1 N6 83.09(15) . . ? N4 Co1 N6 93.81(14) . . ? N1 Co1 N2 81.8(2) . . ? N3 Co1 N2 96.87(16) . . ? N5 Co1 N2 169.84(17) . . ? N4 Co1 N2 92.52(17) . . ? N6 Co1 N2 93.70(14) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1A C1A C2 C17 -75.4(15) . . . . ? O1A C1A C2 C10 163.8(12) . . . . ? O1A C1A C2 C3 50.4(14) . . . . ? O1A C1A C2 C1 -58(3) . . . . ? O1 C1 C2 C1A 2(3) . . . . ? O1 C1 C2 C17 167.0(9) . . . . ? O1 C1 C2 C10 49.3(12) . . . . ? O1 C1 C2 C3 -76.6(11) . . . . ? C1A C2 C3 N1 149.0(7) . . . . ? C17 C2 C3 N1 -79.1(6) . . . . ? C10 C2 C3 N1 40.3(6) . . . . ? C1 C2 C3 N1 170.8(7) . . . . ? N1 C4 C5 N2 -5.4(6) . . . . ? N1 C4 C5 C6 177.2(4) . . . . ? N2 C5 C6 C7 -1.7(8) . . . . ? C4 C5 C6 C7 175.5(6) . . . . ? C5 C6 C7 C8 2.3(10) . . . . ? C6 C7 C8 C9 -3.4(9) . . . . ? C7 C8 C9 N2 4.6(7) . . . . ? C1A C2 C10 N3 167.7(8) . . . . ? C17 C2 C10 N3 39.2(6) . . . . ? C3 C2 C10 N3 -80.8(5) . . . . ? C1 C2 C10 N3 151.8(7) . . . . ? N3 C11 C12 N4 -4.4(6) . . . . ? N3 C11 C12 C13 -179.5(4) . . . . ? N4 C12 C13 C14 3.2(7) . . . . ? C11 C12 C13 C14 177.8(5) . . . . ? C12 C13 C14 C15 -2.8(8) . . . . ? C13 C14 C15 C16 1.9(8) . . . . ? C14 C15 C16 N4 -1.2(7) . . . . ? C1A C2 C17 N5 163.8(9) . . . . ? C10 C2 C17 N5 -78.9(5) . . . . ? C3 C2 C17 N5 40.1(6) . . . . ? C1 C2 C17 N5 157.6(7) . . . . ? N5 C18 C19 N6 -6.3(6) . . . . ? N5 C18 C19 C20 178.4(4) . . . . ? N6 C19 C20 C21 1.6(6) . . . . ? C18 C19 C20 C21 176.5(4) . . . . ? C19 C20 C21 C22 0.3(6) . . . . ? C20 C21 C22 C23 -1.8(6) . . . . ? C21 C22 C23 N6 1.6(6) . . . . ? C5 C4 N1 C3 166.2(4) . . . . ? C5 C4 N1 Co1 1.8(6) . . . . ? C2 C3 N1 C4 -128.3(5) . . . . ? C2 C3 N1 Co1 36.4(6) . . . . ? C8 C9 N2 C5 -4.2(7) . . . . ? C8 C9 N2 Co1 174.5(3) . . . . ? C6 C5 N2 C9 2.7(6) . . . . ? C4 C5 N2 C9 -174.9(4) . . . . ? C6 C5 N2 Co1 -176.3(3) . . . . ? C4 C5 N2 Co1 6.1(4) . . . . ? C12 C11 N3 C10 163.8(5) . . . . ? C12 C11 N3 Co1 1.3(6) . . . . ? C2 C10 N3 C11 -125.1(5) . . . . ? C2 C10 N3 Co1 36.5(6) . . . . ? C15 C16 N4 C12 1.5(6) . . . . ? C15 C16 N4 Co1 178.0(3) . . . . ? C13 C12 N4 C16 -2.4(6) . . . . ? C11 C12 N4 C16 -177.8(4) . . . . ? C13 C12 N4 Co1 -179.6(3) . . . . ? C11 C12 N4 Co1 5.1(4) . . . . ? C19 C18 N5 C17 163.3(4) . . . . ? C19 C18 N5 Co1 5.6(5) . . . . ? C2 C17 N5 C18 -120.2(5) . . . . ? C2 C17 N5 Co1 36.2(5) . . . . ? C22 C23 N6 C19 0.2(6) . . . . ? C22 C23 N6 Co1 179.0(3) . . . . ? C20 C19 N6 C23 -1.9(6) . . . . ? C18 C19 N6 C23 -177.2(4) . . . . ? C20 C19 N6 Co1 179.2(3) . . . . ? C18 C19 N6 Co1 3.8(4) . . . . ? C4 N1 Co1 N3 98.6(4) . . . . ? C3 N1 Co1 N3 -65.7(4) . . . . ? C4 N1 Co1 N5 -174.5(4) . . . . ? C3 N1 Co1 N5 21.2(4) . . . . ? C4 N1 Co1 N4 62.1(11) . . . . ? C3 N1 Co1 N4 -102.2(10) . . . . ? C4 N1 Co1 N6 -91.5(4) . . . . ? C3 N1 Co1 N6 104.1(3) . . . . ? C4 N1 Co1 N2 1.3(4) . . . . ? C3 N1 Co1 N2 -163.0(4) . . . . ? C11 N3 Co1 N1 -171.9(4) . . . . ? C10 N3 Co1 N1 24.9(4) . . . . ? C11 N3 Co1 N5 99.0(4) . . . . ? C10 N3 Co1 N5 -64.2(4) . . . . ? C11 N3 Co1 N4 1.3(4) . . . . ? C10 N3 Co1 N4 -161.9(4) . . . . ? C11 N3 Co1 N6 77.6(10) . . . . ? C10 N3 Co1 N6 -85.6(9) . . . . ? C11 N3 Co1 N2 -90.5(4) . . . . ? C10 N3 Co1 N2 106.3(4) . . . . ? C18 N5 Co1 N1 94.0(3) . . . . ? C17 N5 Co1 N1 -64.3(3) . . . . ? C18 N5 Co1 N3 -178.7(3) . . . . ? C17 N5 Co1 N3 23.0(3) . . . . ? C18 N5 Co1 N4 -95.6(3) . . . . ? C17 N5 Co1 N4 106.1(3) . . . . ? C18 N5 Co1 N6 -2.6(3) . . . . ? C17 N5 Co1 N6 -160.9(3) . . . . ? C18 N5 Co1 N2 69.4(10) . . . . ? C17 N5 Co1 N2 -88.8(10) . . . . ? C16 N4 Co1 N1 -143.7(9) . . . . ? C12 N4 Co1 N1 33.1(11) . . . . ? C16 N4 Co1 N3 179.6(4) . . . . ? C12 N4 Co1 N3 -3.6(3) . . . . ? C16 N4 Co1 N5 93.6(4) . . . . ? C12 N4 Co1 N5 -89.6(3) . . . . ? C16 N4 Co1 N6 10.1(4) . . . . ? C12 N4 Co1 N6 -173.1(3) . . . . ? C16 N4 Co1 N2 -83.8(4) . . . . ? C12 N4 Co1 N2 93.0(3) . . . . ? C23 N6 Co1 N1 92.2(4) . . . . ? C19 N6 Co1 N1 -88.9(3) . . . . ? C23 N6 Co1 N3 -158.1(8) . . . . ? C19 N6 Co1 N3 20.7(10) . . . . ? C23 N6 Co1 N5 -179.6(4) . . . . ? C19 N6 Co1 N5 -0.8(3) . . . . ? C23 N6 Co1 N4 -82.7(3) . . . . ? C19 N6 Co1 N4 96.1(3) . . . . ? C23 N6 Co1 N2 10.1(4) . . . . ? C19 N6 Co1 N2 -171.1(3) . . . . ? C9 N2 Co1 N1 177.1(4) . . . . ? C5 N2 Co1 N1 -4.1(3) . . . . ? C9 N2 Co1 N3 90.9(4) . . . . ? C5 N2 Co1 N3 -90.3(3) . . . . ? C9 N2 Co1 N5 -158.1(8) . . . . ? C5 N2 Co1 N5 20.8(11) . . . . ? C9 N2 Co1 N4 7.1(4) . . . . ? C5 N2 Co1 N4 -174.1(3) . . . . ? C9 N2 Co1 N6 -86.9(4) . . . . ? C5 N2 Co1 N6 91.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.989 _refine_diff_density_min -0.682 _refine_diff_density_rms 0.128 data_1_1 _database_code_depnum_ccdc_archive 'CCDC 845931' #TrackingRef 'combined_final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H24 Fe N6 O1, 2(Cl O4), H2 O' _chemical_formula_sum 'C23 H26 Cl2 Fe N6 O10' _chemical_formula_weight 673.25 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' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Intl_Tables_number 14 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 9.1550(18) _cell_length_b 21.020(4) _cell_length_c 13.998(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.497(3) _cell_angle_gamma 90.00 _cell_volume 2693.6(9) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 11460 _cell_measurement_theta_min 2.424 _cell_measurement_theta_max 28.262 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.410 _exptl_crystal_size_mid 0.290 _exptl_crystal_size_min 0.240 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.660 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1384 _exptl_absorpt_coefficient_mu 0.827 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.717 _exptl_absorpt_correction_T_max 0.813 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2001)' _exptl_special_details ; The crystal was coated in Exxon Paratone N hydrocarbon oil and mounted on a thin mohair fibre attached to a copper pin. Upon mounting on the diffractometer, the crystal was quenched to 150(K) under a cold nitrogen gas stream supplied by an Oxford Cryosystems Cryostream and data were collected at this temperature. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART 1000 CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 0 _diffrn_standards_number 262 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0.1 _diffrn_reflns_number 26280 _diffrn_reflns_av_R_equivalents 0.0230 _diffrn_reflns_av_sigmaI/netI 0.0206 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 28.35 _reflns_number_total 6464 _reflns_number_gt 5376 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1995)' _computing_cell_refinement 'SAINT (Bruker, 1995)' _computing_data_reduction 'SAINT and XPREP (Bruker, 1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ;ORTEP-3 (Farrugia, 1997) WINGX-32 (Farrugia, 1999) ; _computing_publication_material 'enCIFer 1.0 (CCDC, 2003)' _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^)+(0.0546P)^2^+1.9329P] 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 6464 _refine_ls_number_parameters 412 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0484 _refine_ls_R_factor_gt 0.0382 _refine_ls_wR_factor_ref 0.1056 _refine_ls_wR_factor_gt 0.0989 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.4048(3) 0.34757(12) 0.95160(17) 0.0396(5) Uani 1 1 d . . . H1A H -0.3955 0.3089 0.9916 0.048 Uiso 1 1 calc R . . H1B H -0.4078 0.3850 0.9944 0.048 Uiso 1 1 calc R . . C2 C -0.2743(2) 0.35268(10) 0.88476(15) 0.0303(4) Uani 1 1 d . . . C3 C -0.2834(2) 0.29886(10) 0.80978(15) 0.0307(4) Uani 1 1 d . . . H3A H -0.3179 0.2591 0.8401 0.037 Uiso 1 1 calc R . . H3B H -0.3534 0.3106 0.7584 0.037 Uiso 1 1 calc R . . C4 C -0.0812(2) 0.23350(9) 0.76860(14) 0.0300(4) Uani 1 1 d . . . H4 H -0.1360 0.1963 0.7826 0.036 Uiso 1 1 calc R . . C5 C 0.0717(2) 0.23104(9) 0.74444(14) 0.0288(4) Uani 1 1 d . . . C6 C 0.1490(3) 0.17538(10) 0.73182(16) 0.0360(5) Uani 1 1 d . . . H6 H 0.1014 0.1354 0.7373 0.043 Uiso 1 1 calc R . . C7 C 0.2954(3) 0.17814(10) 0.71121(15) 0.0367(5) Uani 1 1 d . . . H7 H 0.3503 0.1404 0.7013 0.044 Uiso 1 1 calc R . . C8 C 0.3605(2) 0.23721(11) 0.70531(16) 0.0359(5) Uani 1 1 d . . . H8 H 0.4613 0.2406 0.6908 0.043 Uiso 1 1 calc R . . C9 C 0.2780(2) 0.29156(10) 0.72057(15) 0.0313(4) Uani 1 1 d . . . H9 H 0.3250 0.3318 0.7177 0.038 Uiso 1 1 calc R . . C10 C -0.2757(2) 0.41760(10) 0.83355(15) 0.0311(4) Uani 1 1 d . . . H10A H -0.3762 0.4281 0.8123 0.037 Uiso 1 1 calc R . . H10B H -0.2417 0.4513 0.8779 0.037 Uiso 1 1 calc R . . C11 C -0.2190(2) 0.43707(9) 0.66978(14) 0.0289(4) Uani 1 1 d . . . H11 H -0.3019 0.4639 0.6629 0.035 Uiso 1 1 calc R . . C12 C -0.1295(2) 0.41906(9) 0.58942(14) 0.0279(4) Uani 1 1 d . . . C13 C -0.1490(2) 0.44186(11) 0.49736(15) 0.0354(5) Uani 1 1 d . . . H13 H -0.2219 0.4727 0.4836 0.042 Uiso 1 1 calc R . . C14 C -0.0602(3) 0.41886(11) 0.42580(15) 0.0394(5) Uani 1 1 d . . . H14 H -0.0699 0.4342 0.3622 0.047 Uiso 1 1 calc R . . C15 C 0.0422(3) 0.37335(11) 0.44831(16) 0.0391(5) Uani 1 1 d . . . H15 H 0.1040 0.3568 0.4001 0.047 Uiso 1 1 calc R . . C16 C 0.0554(2) 0.35162(10) 0.54171(15) 0.0328(4) Uani 1 1 d . . . H16 H 0.1253 0.3195 0.5558 0.039 Uiso 1 1 calc R . . C17 C -0.1325(2) 0.34587(10) 0.94535(14) 0.0315(4) Uani 1 1 d . . . H17A H -0.1414 0.3704 1.0054 0.038 Uiso 1 1 calc R . . H17B H -0.1160 0.3006 0.9618 0.038 Uiso 1 1 calc R . . C18 C 0.0754(2) 0.41257(10) 0.92530(15) 0.0333(4) Uani 1 1 d . . . H18 H 0.0732 0.4239 0.9910 0.040 Uiso 1 1 calc R . . C19 C 0.1751(2) 0.44191(9) 0.85869(15) 0.0305(4) Uani 1 1 d . . . C20 C 0.2877(2) 0.48269(10) 0.88543(17) 0.0365(5) Uani 1 1 d . . . H20 H 0.3042 0.4928 0.9508 0.044 Uiso 1 1 calc R . . C21 C 0.3749(2) 0.50818(10) 0.81550(18) 0.0386(5) Uani 1 1 d . . . H21 H 0.4530 0.5360 0.8318 0.046 Uiso 1 1 calc R . . C22 C 0.3467(2) 0.49267(10) 0.72106(18) 0.0377(5) Uani 1 1 d . . . H22 H 0.4050 0.5100 0.6717 0.045 Uiso 1 1 calc R . . C23 C 0.2325(2) 0.45149(10) 0.69905(16) 0.0317(4) Uani 1 1 d . . . H23 H 0.2145 0.4410 0.6340 0.038 Uiso 1 1 calc R . . N1 N -0.13804(18) 0.28929(7) 0.76994(12) 0.0264(3) Uani 1 1 d . . . N2 N 0.13515(18) 0.28977(7) 0.73915(11) 0.0253(3) Uani 1 1 d . . . N3 N -0.17884(18) 0.41431(7) 0.75079(12) 0.0267(3) Uani 1 1 d . . . N4 N -0.02720(18) 0.37436(7) 0.61286(11) 0.0255(3) Uani 1 1 d . . . N5 N -0.00986(19) 0.37008(8) 0.88945(12) 0.0273(3) Uani 1 1 d . . . N6 N 0.14642(18) 0.42594(7) 0.76616(12) 0.0266(3) Uani 1 1 d . . . O1 O -0.5327(2) 0.34456(10) 0.89694(14) 0.0523(5) Uani 1 1 d . . . H1 H -0.5979 0.3259 0.9281 0.079 Uiso 1 1 calc R . . O2 O -0.2688(2) 0.58323(9) 0.73049(12) 0.0551(5) Uani 1 1 d . . . O3 O -0.07348(19) 0.55334(8) 0.83243(14) 0.0485(4) Uani 1 1 d . . . O4 O -0.15616(19) 0.65892(8) 0.83048(15) 0.0512(5) Uani 1 1 d . . . O5 O -0.30212(18) 0.57876(9) 0.89535(12) 0.0452(4) Uani 1 1 d . . . O6 O -0.3713(2) 0.68334(9) 0.51455(14) 0.0529(5) Uani 0.75 1 d P A 1 O7 O -0.5381(4) 0.6470(2) 0.3957(3) 0.0413(9) Uani 0.50 1 d P A 1 O8 O -0.4568(6) 0.5755(2) 0.5138(4) 0.0705(15) Uani 0.50 1 d P A 1 O9 O -0.6119(4) 0.6608(2) 0.5529(3) 0.0521(10) Uani 0.50 1 d P A 1 O6A O -0.3713(2) 0.68334(9) 0.51455(14) 0.0529(5) Uani 0.25 1 d P B 2 O7A O -0.5463(12) 0.6093(5) 0.5790(8) 0.0698(12) Uiso 0.25 1 d P B 2 O8A O -0.3635(12) 0.5695(5) 0.5097(8) 0.0698(12) Uiso 0.25 1 d P B 2 O9A O -0.5103(16) 0.6243(6) 0.4028(11) 0.0698(12) Uiso 0.25 1 d P B 2 O7B O -0.5854(12) 0.6677(5) 0.4280(8) 0.0698(12) Uiso 0.25 1 d P C 3 O8B O -0.4270(11) 0.5887(5) 0.4540(8) 0.0698(12) Uiso 0.25 1 d P C 3 O9B O -0.5820(15) 0.6345(6) 0.5710(10) 0.0698(12) Uiso 0.25 1 d P C 3 O10 O -0.7943(15) 0.7693(7) 0.4928(9) 0.0479(10) Uiso 0.25 1 d P D 1 O10A O -0.7533(11) 0.7828(5) 0.5091(7) 0.0479(10) Uiso 0.25 1 d P E 2 O10B O -0.8041(11) 0.7769(5) 0.4761(7) 0.0479(10) Uiso 0.30 1 d P F 3 O10C O -0.7574(14) 0.7550(6) 0.5087(8) 0.0479(10) Uiso 0.20 1 d P G 4 Cl1 Cl -0.19978(5) 0.59325(2) 0.82153(4) 0.03274(12) Uani 1 1 d . . . Cl2 Cl -0.49221(17) 0.64169(8) 0.49348(14) 0.0337(3) Uani 0.50 1 d P A 1 Cl2B Cl -0.49221(17) 0.64169(8) 0.49348(14) 0.0337(3) Uani 0.25 1 d P C 3 Cl2A Cl -0.4557(7) 0.6239(3) 0.5050(4) 0.067(2) Uani 0.25 1 d P B 2 Fe1 Fe -0.00880(3) 0.360205(12) 0.752637(18) 0.02236(9) 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 C1 0.0389(12) 0.0445(13) 0.0356(11) -0.0008(10) 0.0075(9) -0.0016(10) C2 0.0324(10) 0.0300(10) 0.0286(10) -0.0001(8) 0.0024(8) -0.0017(8) C3 0.0291(10) 0.0293(10) 0.0338(10) -0.0005(8) 0.0021(8) -0.0057(8) C4 0.0375(11) 0.0224(9) 0.0300(10) -0.0016(7) 0.0005(8) -0.0050(8) C5 0.0378(11) 0.0221(9) 0.0265(9) 0.0001(7) -0.0012(8) -0.0010(8) C6 0.0486(13) 0.0222(9) 0.0373(11) -0.0013(8) 0.0013(9) 0.0029(9) C7 0.0471(12) 0.0289(10) 0.0340(11) -0.0016(8) -0.0018(9) 0.0131(9) C8 0.0325(10) 0.0372(11) 0.0380(11) -0.0016(9) -0.0013(9) 0.0074(9) C9 0.0302(10) 0.0270(10) 0.0365(11) 0.0005(8) -0.0017(8) 0.0011(8) C10 0.0323(10) 0.0294(10) 0.0316(10) -0.0005(8) 0.0028(8) 0.0044(8) C11 0.0297(10) 0.0241(9) 0.0329(10) 0.0016(8) -0.0046(8) 0.0023(7) C12 0.0292(9) 0.0250(9) 0.0294(10) 0.0024(7) -0.0053(7) -0.0031(7) C13 0.0389(11) 0.0351(11) 0.0319(11) 0.0066(8) -0.0077(9) -0.0007(9) C14 0.0507(13) 0.0411(12) 0.0263(10) 0.0060(9) -0.0042(9) -0.0047(10) C15 0.0485(13) 0.0413(12) 0.0277(10) -0.0004(9) 0.0041(9) -0.0014(10) C16 0.0376(11) 0.0309(10) 0.0300(10) 0.0010(8) 0.0012(8) 0.0028(8) C17 0.0393(11) 0.0304(10) 0.0246(9) 0.0015(8) 0.0012(8) -0.0027(8) C18 0.0379(11) 0.0341(11) 0.0279(10) -0.0021(8) -0.0066(8) -0.0008(9) C19 0.0314(10) 0.0235(9) 0.0364(11) 0.0000(8) -0.0075(8) 0.0010(8) C20 0.0362(11) 0.0280(10) 0.0451(12) -0.0029(9) -0.0113(9) -0.0015(8) C21 0.0312(10) 0.0234(10) 0.0609(15) 0.0043(9) -0.0132(10) -0.0024(8) C22 0.0307(10) 0.0274(10) 0.0549(14) 0.0128(9) -0.0031(9) -0.0022(8) C23 0.0319(10) 0.0263(10) 0.0369(11) 0.0085(8) -0.0034(8) -0.0013(8) N1 0.0288(8) 0.0243(8) 0.0261(8) -0.0012(6) -0.0004(6) -0.0045(6) N2 0.0296(8) 0.0210(7) 0.0253(8) 0.0012(6) -0.0020(6) 0.0011(6) N3 0.0283(8) 0.0229(8) 0.0287(8) -0.0003(6) -0.0019(6) 0.0004(6) N4 0.0274(8) 0.0237(8) 0.0255(8) 0.0015(6) -0.0021(6) -0.0027(6) N5 0.0319(9) 0.0242(8) 0.0258(8) 0.0022(6) -0.0041(7) -0.0005(6) N6 0.0268(8) 0.0203(7) 0.0325(8) 0.0029(6) -0.0041(6) 0.0004(6) O1 0.0399(9) 0.0679(12) 0.0493(10) 0.0081(9) 0.0073(8) 0.0003(9) O2 0.0763(13) 0.0521(11) 0.0367(9) 0.0006(8) -0.0153(9) 0.0043(9) O3 0.0411(9) 0.0409(9) 0.0635(11) 0.0021(8) -0.0025(8) 0.0058(7) O4 0.0453(10) 0.0332(9) 0.0753(13) 0.0035(8) 0.0009(9) -0.0131(7) O5 0.0383(9) 0.0528(10) 0.0448(9) 0.0072(8) 0.0036(7) -0.0112(7) O6 0.0450(10) 0.0535(11) 0.0601(11) -0.0111(9) 0.0015(8) -0.0134(8) O7 0.035(2) 0.063(3) 0.0253(16) -0.0039(18) 0.0006(14) -0.0150(19) O8 0.098(4) 0.0198(19) 0.094(4) 0.014(2) -0.008(3) -0.005(2) O9 0.040(2) 0.063(3) 0.053(2) -0.007(2) 0.0230(17) -0.0003(18) O6A 0.0450(10) 0.0535(11) 0.0601(11) -0.0111(9) 0.0015(8) -0.0134(8) Cl1 0.0341(3) 0.0289(2) 0.0352(3) 0.00513(19) -0.00240(19) -0.00471(19) Cl2 0.0341(7) 0.0336(5) 0.0333(6) -0.0022(3) 0.0020(4) -0.0041(4) Cl2B 0.0341(7) 0.0336(5) 0.0333(6) -0.0022(3) 0.0020(4) -0.0041(4) Cl2A 0.052(3) 0.116(7) 0.033(2) -0.014(3) 0.007(2) -0.032(3) Fe1 0.02487(15) 0.01884(14) 0.02334(14) 0.00130(9) -0.00195(10) -0.00062(10) _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 C1 O1 1.394(3) . ? C1 C2 1.528(3) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C10 1.541(3) . ? C2 C3 1.545(3) . ? C2 C17 1.551(3) . ? C3 N1 1.462(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 N1 1.283(3) . ? C4 C5 1.444(3) . ? C4 H4 0.9500 . ? C5 N2 1.367(2) . ? C5 C6 1.380(3) . ? C6 C7 1.374(3) . ? C6 H6 0.9500 . ? C7 C8 1.380(3) . ? C7 H7 0.9500 . ? C8 C9 1.387(3) . ? C8 H8 0.9500 . ? C9 N2 1.336(3) . ? C9 H9 0.9500 . ? C10 N3 1.466(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 N3 1.282(3) . ? C11 C12 1.448(3) . ? C11 H11 0.9500 . ? C12 N4 1.365(3) . ? C12 C13 1.385(3) . ? C13 C14 1.382(3) . ? C13 H13 0.9500 . ? C14 C15 1.374(3) . ? C14 H14 0.9500 . ? C15 C16 1.389(3) . ? C15 H15 0.9500 . ? C16 N4 1.343(3) . ? C16 H16 0.9500 . ? C17 N5 1.465(3) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 N5 1.286(3) . ? C18 C19 1.448(3) . ? C18 H18 0.9500 . ? C19 N6 1.361(3) . ? C19 C20 1.390(3) . ? C20 C21 1.377(3) . ? C20 H20 0.9500 . ? C21 C22 1.383(3) . ? C21 H21 0.9500 . ? C22 C23 1.390(3) . ? C22 H22 0.9500 . ? C23 N6 1.343(3) . ? C23 H23 0.9500 . ? N1 Fe1 1.9197(16) . ? N2 Fe1 1.9921(16) . ? N3 Fe1 1.9279(16) . ? N4 Fe1 1.9848(17) . ? N5 Fe1 1.9264(17) . ? N6 Fe1 1.9900(16) . ? O1 H1 0.8400 . ? O2 Cl1 1.4330(18) . ? O3 Cl1 1.4356(17) . ? O4 Cl1 1.4422(17) . ? O5 Cl1 1.4335(17) . ? O6 Cl2 1.440(3) . ? O7 Cl2 1.433(4) . ? O8 Cl2 1.456(4) . ? O9 Cl2 1.439(4) . ? O7A Cl2A 1.368(12) . ? O8A Cl2A 1.422(13) . ? O9A Cl2A 1.511(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 O1 C1 C2 108.94(19) . . ? O1 C1 H1A 109.9 . . ? C2 C1 H1A 109.9 . . ? O1 C1 H1B 109.9 . . ? C2 C1 H1B 109.9 . . ? H1A C1 H1B 108.3 . . ? C1 C2 C10 110.11(17) . . ? C1 C2 C3 109.04(17) . . ? C10 C2 C3 109.40(17) . . ? C1 C2 C17 108.29(17) . . ? C10 C2 C17 109.85(17) . . ? C3 C2 C17 110.13(17) . . ? N1 C3 C2 108.40(16) . . ? N1 C3 H3A 110.0 . . ? C2 C3 H3A 110.0 . . ? N1 C3 H3B 110.0 . . ? C2 C3 H3B 110.0 . . ? H3A C3 H3B 108.4 . . ? N1 C4 C5 115.49(17) . . ? N1 C4 H4 122.3 . . ? C5 C4 H4 122.3 . . ? N2 C5 C6 122.70(19) . . ? N2 C5 C4 113.18(17) . . ? C6 C5 C4 124.06(18) . . ? C7 C6 C5 119.6(2) . . ? C7 C6 H6 120.2 . . ? C5 C6 H6 120.2 . . ? C6 C7 C8 118.21(19) . . ? C6 C7 H7 120.9 . . ? C8 C7 H7 120.9 . . ? C7 C8 C9 119.7(2) . . ? C7 C8 H8 120.1 . . ? C9 C8 H8 120.1 . . ? N2 C9 C8 122.82(19) . . ? N2 C9 H9 118.6 . . ? C8 C9 H9 118.6 . . ? N3 C10 C2 108.85(16) . . ? N3 C10 H10A 109.9 . . ? C2 C10 H10A 109.9 . . ? N3 C10 H10B 109.9 . . ? C2 C10 H10B 109.9 . . ? H10A C10 H10B 108.3 . . ? N3 C11 C12 115.45(18) . . ? N3 C11 H11 122.3 . . ? C12 C11 H11 122.3 . . ? N4 C12 C13 122.97(19) . . ? N4 C12 C11 112.65(17) . . ? C13 C12 C11 124.30(19) . . ? C14 C13 C12 118.8(2) . . ? C14 C13 H13 120.6 . . ? C12 C13 H13 120.6 . . ? C15 C14 C13 118.8(2) . . ? C15 C14 H14 120.6 . . ? C13 C14 H14 120.6 . . ? C14 C15 C16 119.9(2) . . ? C14 C15 H15 120.1 . . ? C16 C15 H15 120.1 . . ? N4 C16 C15 122.4(2) . . ? N4 C16 H16 118.8 . . ? C15 C16 H16 118.8 . . ? N5 C17 C2 108.51(16) . . ? N5 C17 H17A 110.0 . . ? C2 C17 H17A 110.0 . . ? N5 C17 H17B 110.0 . . ? C2 C17 H17B 110.0 . . ? H17A C17 H17B 108.4 . . ? N5 C18 C19 115.36(19) . . ? N5 C18 H18 122.3 . . ? C19 C18 H18 122.3 . . ? N6 C19 C20 123.0(2) . . ? N6 C19 C18 113.00(17) . . ? C20 C19 C18 124.0(2) . . ? C21 C20 C19 118.8(2) . . ? C21 C20 H20 120.6 . . ? C19 C20 H20 120.6 . . ? C20 C21 C22 118.9(2) . . ? C20 C21 H21 120.5 . . ? C22 C21 H21 120.5 . . ? C21 C22 C23 119.5(2) . . ? C21 C22 H22 120.3 . . ? C23 C22 H22 120.3 . . ? N6 C23 C22 122.6(2) . . ? N6 C23 H23 118.7 . . ? C22 C23 H23 118.7 . . ? C4 N1 C3 120.15(17) . . ? C4 N1 Fe1 117.21(14) . . ? C3 N1 Fe1 120.37(13) . . ? C9 N2 C5 116.95(17) . . ? C9 N2 Fe1 130.31(13) . . ? C5 N2 Fe1 112.60(13) . . ? C11 N3 C10 120.70(17) . . ? C11 N3 Fe1 117.24(14) . . ? C10 N3 Fe1 120.72(13) . . ? C16 N4 C12 117.14(17) . . ? C16 N4 Fe1 129.35(14) . . ? C12 N4 Fe1 113.10(13) . . ? C18 N5 C17 119.90(18) . . ? C18 N5 Fe1 117.05(15) . . ? C17 N5 Fe1 120.26(13) . . ? C23 N6 C19 117.23(17) . . ? C23 N6 Fe1 129.33(14) . . ? C19 N6 Fe1 113.15(13) . . ? C1 O1 H1 109.5 . . ? O2 Cl1 O5 108.91(12) . . ? O2 Cl1 O3 110.91(12) . . ? O5 Cl1 O3 109.27(11) . . ? O2 Cl1 O4 109.72(11) . . ? O5 Cl1 O4 108.85(11) . . ? O3 Cl1 O4 109.15(11) . . ? O7 Cl2 O9 108.2(3) . . ? O7 Cl2 O6 111.5(2) . . ? O9 Cl2 O6 107.5(2) . . ? O7 Cl2 O8 108.9(3) . . ? O9 Cl2 O8 108.8(3) . . ? O6 Cl2 O8 111.8(3) . . ? O7A Cl2A O8A 98.5(8) . . ? O7A Cl2A O9A 121.5(8) . . ? O8A Cl2A O9A 103.9(8) . . ? N1 Fe1 N5 87.12(7) . . ? N1 Fe1 N3 87.78(7) . . ? N5 Fe1 N3 86.49(7) . . ? N1 Fe1 N4 101.17(7) . . ? N5 Fe1 N4 164.31(7) . . ? N3 Fe1 N4 80.60(7) . . ? N1 Fe1 N6 165.36(7) . . ? N5 Fe1 N6 80.82(7) . . ? N3 Fe1 N6 99.65(7) . . ? N4 Fe1 N6 92.53(7) . . ? N1 Fe1 N2 81.02(7) . . ? N5 Fe1 N2 100.56(7) . . ? N3 Fe1 N2 166.38(7) . . ? N4 Fe1 N2 93.93(7) . . ? N6 Fe1 N2 93.02(7) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C10 68.2(2) . . . . ? O1 C1 C2 C3 -51.9(2) . . . . ? O1 C1 C2 C17 -171.69(18) . . . . ? C1 C2 C3 N1 -159.60(17) . . . . ? C10 C2 C3 N1 79.9(2) . . . . ? C17 C2 C3 N1 -40.9(2) . . . . ? N1 C4 C5 N2 8.1(3) . . . . ? N1 C4 C5 C6 -174.60(19) . . . . ? N2 C5 C6 C7 -1.3(3) . . . . ? C4 C5 C6 C7 -178.4(2) . . . . ? C5 C6 C7 C8 1.0(3) . . . . ? C6 C7 C8 C9 0.3(3) . . . . ? C7 C8 C9 N2 -1.4(3) . . . . ? C1 C2 C10 N3 -163.19(17) . . . . ? C3 C2 C10 N3 -43.4(2) . . . . ? C17 C2 C10 N3 77.6(2) . . . . ? N3 C11 C12 N4 7.4(2) . . . . ? N3 C11 C12 C13 -175.63(19) . . . . ? N4 C12 C13 C14 -0.5(3) . . . . ? C11 C12 C13 C14 -177.2(2) . . . . ? C12 C13 C14 C15 1.2(3) . . . . ? C13 C14 C15 C16 -0.3(3) . . . . ? C14 C15 C16 N4 -1.3(4) . . . . ? C1 C2 C17 N5 -162.53(17) . . . . ? C10 C2 C17 N5 -42.2(2) . . . . ? C3 C2 C17 N5 78.3(2) . . . . ? N5 C18 C19 N6 9.1(3) . . . . ? N5 C18 C19 C20 -171.5(2) . . . . ? N6 C19 C20 C21 -0.1(3) . . . . ? C18 C19 C20 C21 -179.5(2) . . . . ? C19 C20 C21 C22 0.4(3) . . . . ? C20 C21 C22 C23 -0.5(3) . . . . ? C21 C22 C23 N6 0.3(3) . . . . ? C5 C4 N1 C3 -168.99(17) . . . . ? C5 C4 N1 Fe1 -6.0(2) . . . . ? C2 C3 N1 C4 127.63(19) . . . . ? C2 C3 N1 Fe1 -34.8(2) . . . . ? C8 C9 N2 C5 1.1(3) . . . . ? C8 C9 N2 Fe1 -174.24(16) . . . . ? C6 C5 N2 C9 0.2(3) . . . . ? C4 C5 N2 C9 177.61(17) . . . . ? C6 C5 N2 Fe1 176.42(16) . . . . ? C4 C5 N2 Fe1 -6.2(2) . . . . ? C12 C11 N3 C10 -167.10(17) . . . . ? C12 C11 N3 Fe1 -0.3(2) . . . . ? C2 C10 N3 C11 135.27(19) . . . . ? C2 C10 N3 Fe1 -31.1(2) . . . . ? C15 C16 N4 C12 2.0(3) . . . . ? C15 C16 N4 Fe1 -170.10(17) . . . . ? C13 C12 N4 C16 -1.0(3) . . . . ? C11 C12 N4 C16 175.98(17) . . . . ? C13 C12 N4 Fe1 172.31(16) . . . . ? C11 C12 N4 Fe1 -10.7(2) . . . . ? C19 C18 N5 C17 -168.70(17) . . . . ? C19 C18 N5 Fe1 -7.6(2) . . . . ? C2 C17 N5 C18 126.90(19) . . . . ? C2 C17 N5 Fe1 -33.6(2) . . . . ? C22 C23 N6 C19 0.0(3) . . . . ? C22 C23 N6 Fe1 -173.36(15) . . . . ? C20 C19 N6 C23 -0.1(3) . . . . ? C18 C19 N6 C23 179.32(17) . . . . ? C20 C19 N6 Fe1 174.32(16) . . . . ? C18 C19 N6 Fe1 -6.3(2) . . . . ? C4 N1 Fe1 N5 -99.17(16) . . . . ? C3 N1 Fe1 N5 63.74(15) . . . . ? C4 N1 Fe1 N3 174.24(16) . . . . ? C3 N1 Fe1 N3 -22.85(15) . . . . ? C4 N1 Fe1 N4 94.27(15) . . . . ? C3 N1 Fe1 N4 -102.82(15) . . . . ? C4 N1 Fe1 N6 -64.8(3) . . . . ? C3 N1 Fe1 N6 98.2(3) . . . . ? C4 N1 Fe1 N2 2.01(15) . . . . ? C3 N1 Fe1 N2 164.92(16) . . . . ? C18 N5 Fe1 N1 174.89(16) . . . . ? C17 N5 Fe1 N1 -24.07(15) . . . . ? C18 N5 Fe1 N3 -97.16(16) . . . . ? C17 N5 Fe1 N3 63.88(15) . . . . ? C18 N5 Fe1 N4 -62.6(3) . . . . ? C17 N5 Fe1 N4 98.5(3) . . . . ? C18 N5 Fe1 N6 3.21(15) . . . . ? C17 N5 Fe1 N6 164.25(15) . . . . ? C18 N5 Fe1 N2 94.59(16) . . . . ? C17 N5 Fe1 N2 -104.37(15) . . . . ? C11 N3 Fe1 N1 -106.12(15) . . . . ? C10 N3 Fe1 N1 60.69(15) . . . . ? C11 N3 Fe1 N5 166.63(15) . . . . ? C10 N3 Fe1 N5 -26.56(15) . . . . ? C11 N3 Fe1 N4 -4.41(14) . . . . ? C10 N3 Fe1 N4 162.39(15) . . . . ? C11 N3 Fe1 N6 86.57(15) . . . . ? C10 N3 Fe1 N6 -106.62(15) . . . . ? C11 N3 Fe1 N2 -71.6(3) . . . . ? C10 N3 Fe1 N2 95.2(3) . . . . ? C16 N4 Fe1 N1 -93.46(18) . . . . ? C12 N4 Fe1 N1 94.21(14) . . . . ? C16 N4 Fe1 N5 145.6(2) . . . . ? C12 N4 Fe1 N5 -26.7(3) . . . . ? C16 N4 Fe1 N3 -179.29(18) . . . . ? C12 N4 Fe1 N3 8.38(13) . . . . ? C16 N4 Fe1 N6 81.34(18) . . . . ? C12 N4 Fe1 N6 -90.98(14) . . . . ? C16 N4 Fe1 N2 -11.85(18) . . . . ? C12 N4 Fe1 N2 175.82(13) . . . . ? C23 N6 Fe1 N1 140.7(3) . . . . ? C19 N6 Fe1 N1 -32.8(3) . . . . ? C23 N6 Fe1 N5 175.60(18) . . . . ? C19 N6 Fe1 N5 2.04(13) . . . . ? C23 N6 Fe1 N3 -99.58(17) . . . . ? C19 N6 Fe1 N3 86.86(14) . . . . ? C23 N6 Fe1 N4 -18.69(17) . . . . ? C19 N6 Fe1 N4 167.75(14) . . . . ? C23 N6 Fe1 N2 75.38(17) . . . . ? C19 N6 Fe1 N2 -98.18(14) . . . . ? C9 N2 Fe1 N1 178.12(19) . . . . ? C5 N2 Fe1 N1 2.59(13) . . . . ? C9 N2 Fe1 N5 -96.54(18) . . . . ? C5 N2 Fe1 N5 87.93(14) . . . . ? C9 N2 Fe1 N3 143.1(3) . . . . ? C5 N2 Fe1 N3 -32.4(4) . . . . ? C9 N2 Fe1 N4 77.42(18) . . . . ? C5 N2 Fe1 N4 -98.11(14) . . . . ? C9 N2 Fe1 N6 -15.32(18) . . . . ? C5 N2 Fe1 N6 169.14(13) . . . . ? 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 O1 H1 O10A 0.84 1.86 2.702(10) 176.9 2_346 O1 H1 O10 0.84 1.91 2.727(15) 165.3 2_346 O1 H1 O10B 0.84 1.92 2.731(11) 162.2 2_346 O1 H1 O10C 0.84 2.19 3.005(11) 164.8 2_346 _diffrn_measured_fraction_theta_max 0.960 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.895 _refine_diff_density_min -0.441 _refine_diff_density_rms 0.070 data_1_2 _database_code_depnum_ccdc_archive 'CCDC 845932' #TrackingRef 'combined_final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H24 N6 Ni O, 2(Cl O4), 0.85(C H4 O)' _chemical_formula_sum 'C23.85 H27.40 Cl2 N6 Ni O9.85' _chemical_formula_weight 685.33 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' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Intl_Tables_number 14 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 9.4909(6) _cell_length_b 21.0191(12) _cell_length_c 14.1218(8) _cell_angle_alpha 90.00 _cell_angle_beta 94.268(3) _cell_angle_gamma 90.00 _cell_volume 2809.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9790 _cell_measurement_theta_min 2.360 _cell_measurement_theta_max 29.914 _exptl_crystal_description plate _exptl_crystal_colour green _exptl_crystal_size_max 0.280 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.050 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.620 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1413 _exptl_absorpt_coefficient_mu 0.948 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.871 _exptl_absorpt_correction_T_max 0.954 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; The crystal was coated in Exxon Paratone N hydrocarbon oil and mounted on a thin mohair fibre attached to a copper pin. Upon mounting on the diffractometer, the crystal was quenched to 150(K) under a cold nitrogen gas stream supplied by an Oxford Cryosystems Cryostream and data were collected at this temperature. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type APEXII-FR591 _diffrn_measurement_method \w+\f _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 61504 _diffrn_reflns_av_R_equivalents 0.0350 _diffrn_reflns_av_sigmaI/netI 0.0243 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.50 _diffrn_reflns_theta_max 30.02 _reflns_number_total 8191 _reflns_number_gt 6671 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX (Bruker-Nonius, 2003)' _computing_cell_refinement 'SAINT (Bruker-Nonius, 2003)' _computing_data_reduction 'SAINT (Bruker-Nonius, 2003), XPREP (Bruker-Nonius, 2003)' _computing_structure_solution 'SIR97 (Altomare, et. al. 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ;ORTEP-3 (Farrugia, 1997) WINGX-32 (Farrugia, 1999) ; _computing_publication_material 'enCIFer 1.1 (CCDC, 2005)' _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^)+(0.0482P)^2^+1.8010P] 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 8191 _refine_ls_number_parameters 408 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0493 _refine_ls_R_factor_gt 0.0369 _refine_ls_wR_factor_ref 0.0999 _refine_ls_wR_factor_gt 0.0932 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.1250(2) 0.15486(11) 0.92574(15) 0.0348(4) Uani 1 1 d . . . H1A H 0.1215 0.1165 0.9662 0.042 Uiso 1 1 calc R . . H1B H 0.1371 0.1925 0.9677 0.042 Uiso 1 1 calc R . . C2 C 0.25015(18) 0.14994(8) 0.86278(13) 0.0251(3) Uani 1 1 d . . . C3 C 0.24386(18) 0.20735(9) 0.79401(13) 0.0273(3) Uani 1 1 d . . . H3A H 0.1715 0.1996 0.7411 0.033 Uiso 1 1 calc R . . H3B H 0.2170 0.2462 0.8280 0.033 Uiso 1 1 calc R . . C4 C 0.4437(2) 0.27079(8) 0.76173(13) 0.0277(4) Uani 1 1 d . . . H4 H 0.3962 0.3076 0.7820 0.033 Uiso 1 1 calc R . . C5 C 0.59092(19) 0.27385(8) 0.73530(12) 0.0255(3) Uani 1 1 d . . . C6 C 0.78848(18) 0.21646(9) 0.70191(13) 0.0278(4) Uani 1 1 d . . . H6 H 0.8343 0.1767 0.6952 0.033 Uiso 1 1 calc R . . C7 C 0.8643(2) 0.27213(10) 0.68809(14) 0.0336(4) Uani 1 1 d . . . H7 H 0.9588 0.2702 0.6703 0.040 Uiso 1 1 calc R . . C8 C 0.7997(2) 0.33002(10) 0.70064(15) 0.0358(4) Uani 1 1 d . . . H8 H 0.8496 0.3686 0.6926 0.043 Uiso 1 1 calc R . . C9 C 0.6607(2) 0.33108(9) 0.72514(14) 0.0337(4) Uani 1 1 d . . . H9 H 0.6143 0.3703 0.7348 0.040 Uiso 1 1 calc R . . C10 C 0.38570(19) 0.15178(9) 0.93093(13) 0.0267(3) Uani 1 1 d . . . H10A H 0.4035 0.1959 0.9531 0.032 Uiso 1 1 calc R . . H10B H 0.3725 0.1248 0.9871 0.032 Uiso 1 1 calc R . . C11 C 0.5796(2) 0.08040(10) 0.91605(13) 0.0309(4) Uani 1 1 d . . . H11 H 0.5635 0.0624 0.9760 0.037 Uiso 1 1 calc R . . C12 C 0.68757(18) 0.05455(8) 0.85716(13) 0.0263(3) Uani 1 1 d . . . C13 C 0.76820(18) 0.05021(8) 0.70708(14) 0.0269(3) Uani 1 1 d . . . H13 H 0.7589 0.0623 0.6421 0.032 Uiso 1 1 calc R . . C14 C 0.87925(19) 0.01017(9) 0.73827(15) 0.0316(4) Uani 1 1 d . . . H14 H 0.9440 -0.0048 0.6952 0.038 Uiso 1 1 calc R . . C15 C 0.8934(2) -0.00720(9) 0.83231(16) 0.0340(4) Uani 1 1 d . . . H15 H 0.9693 -0.0338 0.8554 0.041 Uiso 1 1 calc R . . C16 C 0.7954(2) 0.01458(9) 0.89334(15) 0.0325(4) Uani 1 1 d . . . H16 H 0.8020 0.0024 0.9583 0.039 Uiso 1 1 calc R . . C17 C 0.23773(19) 0.08606(9) 0.80791(13) 0.0272(4) Uani 1 1 d . . . H17A H 0.2632 0.0505 0.8518 0.033 Uiso 1 1 calc R . . H17B H 0.1390 0.0798 0.7819 0.033 Uiso 1 1 calc R . . C18 C 0.28947(19) 0.06580(8) 0.64768(13) 0.0270(3) Uani 1 1 d . . . H18 H 0.2035 0.0429 0.6373 0.032 Uiso 1 1 calc R . . C19 C 0.37961(18) 0.07939(8) 0.56958(12) 0.0240(3) Uani 1 1 d . . . C20 C 0.5681(2) 0.13740(9) 0.52242(13) 0.0291(4) Uani 1 1 d . . . H20 H 0.6432 0.1665 0.5370 0.035 Uiso 1 1 calc R . . C21 C 0.5473(2) 0.11454(10) 0.42968(14) 0.0344(4) Uani 1 1 d . . . H21 H 0.6073 0.1275 0.3823 0.041 Uiso 1 1 calc R . . C22 C 0.4375(2) 0.07262(10) 0.40818(14) 0.0353(4) Uani 1 1 d . . . H22 H 0.4214 0.0560 0.3458 0.042 Uiso 1 1 calc R . . C23 C 0.3509(2) 0.05511(9) 0.47875(13) 0.0311(4) Uani 1 1 d . . . H23 H 0.2736 0.0271 0.4652 0.037 Uiso 1 1 calc R . . N1 N 0.38238(15) 0.21659(7) 0.75622(11) 0.0250(3) Uani 1 1 d . . . N2 N 0.65384(15) 0.21675(7) 0.72420(10) 0.0233(3) Uani 1 1 d . . . N3 N 0.50747(16) 0.12871(7) 0.88260(11) 0.0250(3) Uani 1 1 d . . . N4 N 0.67423(15) 0.07231(7) 0.76499(11) 0.0232(3) Uani 1 1 d . . . N5 N 0.33216(15) 0.08625(7) 0.73003(11) 0.0257(3) Uani 1 1 d . . . N6 N 0.48747(15) 0.12024(7) 0.59140(10) 0.0236(3) Uani 1 1 d . . . O1 O -0.00090(16) 0.16036(9) 0.86815(12) 0.0458(4) Uani 1 1 d . . . H1 H -0.0659 0.1724 0.9012 0.069 Uiso 1 1 calc R . . C1M C 0.2485(3) 0.74531(16) 0.0082(3) 0.0582(8) Uani 0.85 1 d P . . H1M1 H 0.3462 0.7566 0.0288 0.087 Uiso 0.85 1 calc PR . . H1M2 H 0.2464 0.7236 -0.0533 0.087 Uiso 0.85 1 calc PR . . H1M3 H 0.2106 0.7170 0.0552 0.087 Uiso 0.85 1 calc PR . . O1M O 0.1711(3) 0.79731(12) -0.00013(19) 0.0729(8) Uani 0.85 1 d P . . H1M H 0.2037 0.8216 -0.0404 0.109 Uiso 0.85 1 calc PR . . O2 O 0.33631(19) 0.84317(8) 0.82600(17) 0.0620(5) Uani 1 1 d . . . O3 O 0.42819(17) 0.94671(8) 0.83846(13) 0.0490(4) Uani 1 1 d . . . O4 O 0.21193(16) 0.92256(9) 0.90023(11) 0.0483(4) Uani 1 1 d . . . O5 O 0.2246(2) 0.92531(9) 0.73643(11) 0.0539(4) Uani 1 1 d . . . O6 O -0.0606(2) 0.88086(10) 0.57654(14) 0.0594(5) Uani 1 1 d . . . O7 O 0.12801(16) 0.81793(8) 0.53127(12) 0.0459(4) Uani 1 1 d . . . Cl1 Cl 0.30096(5) 0.90959(2) 0.82411(3) 0.03004(10) Uani 1 1 d . . . Cl2 Cl 0.04130(7) 0.87352(4) 0.50759(4) 0.03529(13) Uani 0.85 1 d P A 1 O8 O 0.1292(2) 0.93006(10) 0.50750(16) 0.0510(5) Uani 0.85 1 d P A 1 O9 O -0.0260(2) 0.86422(12) 0.41319(15) 0.0571(6) Uani 0.85 1 d P A 1 Cl2A Cl -0.0067(4) 0.84748(17) 0.4983(3) 0.0303(7) Uani 0.15 1 d P A 2 O8A O 0.048(2) 0.9091(11) 0.4532(17) 0.108(6) Uiso 0.15 1 d P A 2 O9A O -0.097(2) 0.8216(11) 0.4381(15) 0.108(6) Uiso 0.15 1 d P A 2 Ni1 Ni 0.51314(2) 0.140576(10) 0.736937(15) 0.01999(6) 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 C1 0.0304(9) 0.0426(11) 0.0325(10) -0.0009(8) 0.0092(8) 0.0016(8) C2 0.0248(7) 0.0255(8) 0.0254(8) -0.0011(6) 0.0040(6) 0.0007(6) C3 0.0235(7) 0.0266(8) 0.0321(9) -0.0001(7) 0.0049(7) 0.0030(6) C4 0.0321(8) 0.0220(8) 0.0293(9) 0.0011(7) 0.0039(7) 0.0027(7) C5 0.0316(8) 0.0217(8) 0.0234(8) -0.0003(6) 0.0029(7) -0.0020(7) C6 0.0261(8) 0.0266(9) 0.0309(9) 0.0004(7) 0.0024(7) -0.0025(7) C7 0.0307(9) 0.0369(10) 0.0335(10) 0.0011(8) 0.0037(8) -0.0097(8) C8 0.0451(11) 0.0275(9) 0.0352(10) 0.0003(8) 0.0060(9) -0.0146(8) C9 0.0461(11) 0.0214(8) 0.0344(10) -0.0009(7) 0.0088(8) -0.0045(8) C10 0.0283(8) 0.0294(9) 0.0227(8) -0.0026(7) 0.0033(7) 0.0021(7) C11 0.0328(9) 0.0358(10) 0.0238(9) 0.0017(7) -0.0006(7) 0.0064(8) C12 0.0259(8) 0.0227(8) 0.0296(9) -0.0018(7) -0.0019(7) 0.0007(6) C13 0.0271(8) 0.0217(8) 0.0323(9) -0.0057(7) 0.0045(7) -0.0016(6) C14 0.0256(8) 0.0227(8) 0.0466(11) -0.0097(8) 0.0042(8) -0.0006(7) C15 0.0277(8) 0.0240(9) 0.0491(12) -0.0057(8) -0.0058(8) 0.0056(7) C16 0.0334(9) 0.0278(9) 0.0349(10) 0.0014(8) -0.0059(8) 0.0046(7) C17 0.0266(8) 0.0262(8) 0.0293(9) -0.0007(7) 0.0057(7) -0.0049(7) C18 0.0273(8) 0.0240(8) 0.0293(9) -0.0006(7) 0.0001(7) -0.0045(7) C19 0.0278(8) 0.0204(8) 0.0232(8) -0.0006(6) -0.0027(6) 0.0011(6) C20 0.0306(8) 0.0309(9) 0.0260(9) -0.0005(7) 0.0029(7) -0.0027(7) C21 0.0412(10) 0.0386(10) 0.0239(9) 0.0003(8) 0.0065(8) -0.0007(9) C22 0.0460(11) 0.0373(10) 0.0220(9) -0.0040(8) -0.0021(8) 0.0006(9) C23 0.0370(9) 0.0282(9) 0.0271(9) -0.0028(7) -0.0053(7) -0.0025(7) N1 0.0243(6) 0.0231(7) 0.0277(7) 0.0011(6) 0.0021(6) 0.0014(5) N2 0.0255(6) 0.0205(6) 0.0236(7) -0.0006(5) 0.0004(5) -0.0030(5) N3 0.0253(7) 0.0261(7) 0.0235(7) -0.0014(6) 0.0013(6) 0.0022(5) N4 0.0243(6) 0.0186(6) 0.0264(7) -0.0019(5) -0.0002(5) -0.0010(5) N5 0.0253(7) 0.0266(7) 0.0251(7) -0.0025(6) 0.0020(6) -0.0035(6) N6 0.0246(6) 0.0230(7) 0.0230(7) -0.0009(5) -0.0004(5) -0.0008(5) O1 0.0305(7) 0.0637(11) 0.0437(9) -0.0009(8) 0.0068(6) 0.0038(7) C1M 0.0518(17) 0.059(2) 0.063(2) -0.0034(16) 0.0021(15) -0.0082(15) O1M 0.0846(17) 0.0663(15) 0.0755(17) 0.0225(12) 0.0571(14) 0.0235(13) O2 0.0499(10) 0.0292(8) 0.1056(17) -0.0070(9) -0.0030(10) 0.0135(7) O3 0.0392(8) 0.0406(9) 0.0673(11) 0.0030(8) 0.0056(8) -0.0041(7) O4 0.0378(8) 0.0748(12) 0.0330(8) -0.0038(8) 0.0066(6) 0.0126(8) O5 0.0671(11) 0.0643(11) 0.0288(8) 0.0019(8) -0.0070(8) 0.0040(9) O6 0.0481(10) 0.0778(13) 0.0549(11) 0.0034(10) 0.0210(8) 0.0132(9) O7 0.0407(8) 0.0441(9) 0.0541(10) 0.0134(7) 0.0121(7) 0.0099(7) Cl1 0.0324(2) 0.0274(2) 0.0306(2) -0.00207(16) 0.00383(17) 0.00667(16) Cl2 0.0316(3) 0.0423(4) 0.0328(3) 0.0059(3) 0.0084(2) 0.0058(3) O8 0.0595(12) 0.0402(10) 0.0544(12) 0.0092(9) 0.0123(10) -0.0051(9) O9 0.0509(12) 0.0825(17) 0.0373(11) 0.0011(10) -0.0019(9) 0.0130(11) Cl2A 0.0264(14) 0.0260(15) 0.0388(18) -0.0030(13) 0.0032(12) -0.0123(12) Ni1 0.02072(10) 0.01832(11) 0.02078(11) -0.00139(8) 0.00045(7) -0.00065(7) _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 C1 O1 1.399(3) . ? C1 C2 1.539(3) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.547(3) . ? C2 C10 1.549(2) . ? C2 C17 1.550(2) . ? C3 N1 1.468(2) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 N1 1.279(2) . ? C4 C5 1.475(3) . ? C4 H4 0.9500 . ? C5 N2 1.355(2) . ? C5 C9 1.386(2) . ? C6 N2 1.339(2) . ? C6 C7 1.395(3) . ? C6 H6 0.9500 . ? C7 C8 1.380(3) . ? C7 H7 0.9500 . ? C8 C9 1.389(3) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 N3 1.468(2) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 N3 1.294(2) . ? C11 C12 1.471(3) . ? C11 H11 0.9500 . ? C12 N4 1.351(2) . ? C12 C16 1.392(2) . ? C13 N4 1.337(2) . ? C13 C14 1.394(3) . ? C13 H13 0.9500 . ? C14 C15 1.374(3) . ? C14 H14 0.9500 . ? C15 C16 1.392(3) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 N5 1.470(2) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 N5 1.277(2) . ? C18 C19 1.473(3) . ? C18 H18 0.9500 . ? C19 N6 1.354(2) . ? C19 C23 1.389(2) . ? C20 N6 1.333(2) . ? C20 C21 1.395(3) . ? C20 H20 0.9500 . ? C21 C22 1.381(3) . ? C21 H21 0.9500 . ? C22 C23 1.388(3) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? N1 Ni1 2.0537(15) . ? N2 Ni1 2.1012(14) . ? N3 Ni1 2.0768(15) . ? N4 Ni1 2.1126(14) . ? N5 Ni1 2.0588(14) . ? N6 Ni1 2.0957(15) . ? O1 H1 0.8400 . ? C1M O1M 1.317(4) . ? C1M H1M1 0.9800 . ? C1M H1M2 0.9800 . ? C1M H1M3 0.9800 . ? O1M H1M 0.8400 . ? O2 Cl1 1.4356(16) . ? O3 Cl1 1.4393(16) . ? O4 Cl1 1.4419(16) . ? O5 Cl1 1.4262(17) . ? O6 Cl2 1.4311(18) . ? O6 Cl2A 1.435(4) . ? O7 Cl2 1.4536(16) . ? O7 Cl2A 1.466(4) . ? Cl2 O9 1.448(2) . ? Cl2 O8 1.452(2) . ? Cl2A O9A 1.28(2) . ? Cl2A O8A 1.55(2) . ? 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 C1 C2 109.40(16) . . ? O1 C1 H1A 109.8 . . ? C2 C1 H1A 109.8 . . ? O1 C1 H1B 109.8 . . ? C2 C1 H1B 109.8 . . ? H1A C1 H1B 108.2 . . ? C1 C2 C3 108.35(15) . . ? C1 C2 C10 106.30(15) . . ? C3 C2 C10 111.23(14) . . ? C1 C2 C17 108.27(15) . . ? C3 C2 C17 111.33(15) . . ? C10 C2 C17 111.15(14) . . ? N1 C3 C2 109.73(14) . . ? N1 C3 H3A 109.7 . . ? C2 C3 H3A 109.7 . . ? N1 C3 H3B 109.7 . . ? C2 C3 H3B 109.7 . . ? H3A C3 H3B 108.2 . . ? N1 C4 C5 117.31(16) . . ? N1 C4 H4 121.3 . . ? C5 C4 H4 121.3 . . ? N2 C5 C9 122.61(17) . . ? N2 C5 C4 115.14(15) . . ? C9 C5 C4 122.23(17) . . ? N2 C6 C7 122.70(18) . . ? N2 C6 H6 118.6 . . ? C7 C6 H6 118.6 . . ? C8 C7 C6 118.88(18) . . ? C8 C7 H7 120.6 . . ? C6 C7 H7 120.6 . . ? C7 C8 C9 119.05(17) . . ? C7 C8 H8 120.5 . . ? C9 C8 H8 120.5 . . ? C5 C9 C8 118.82(18) . . ? C5 C9 H9 120.6 . . ? C8 C9 H9 120.6 . . ? N3 C10 C2 110.44(14) . . ? N3 C10 H10A 109.6 . . ? C2 C10 H10A 109.6 . . ? N3 C10 H10B 109.6 . . ? C2 C10 H10B 109.6 . . ? H10A C10 H10B 108.1 . . ? N3 C11 C12 117.09(17) . . ? N3 C11 H11 121.5 . . ? C12 C11 H11 121.5 . . ? N4 C12 C16 122.28(17) . . ? N4 C12 C11 115.05(15) . . ? C16 C12 C11 122.67(17) . . ? N4 C13 C14 122.64(18) . . ? N4 C13 H13 118.7 . . ? C14 C13 H13 118.7 . . ? C15 C14 C13 118.87(18) . . ? C15 C14 H14 120.6 . . ? C13 C14 H14 120.6 . . ? C14 C15 C16 119.30(17) . . ? C14 C15 H15 120.4 . . ? C16 C15 H15 120.4 . . ? C15 C16 C12 118.58(19) . . ? C15 C16 H16 120.7 . . ? C12 C16 H16 120.7 . . ? N5 C17 C2 110.11(14) . . ? N5 C17 H17A 109.6 . . ? C2 C17 H17A 109.6 . . ? N5 C17 H17B 109.6 . . ? C2 C17 H17B 109.6 . . ? H17A C17 H17B 108.2 . . ? N5 C18 C19 116.99(15) . . ? N5 C18 H18 121.5 . . ? C19 C18 H18 121.5 . . ? N6 C19 C23 122.42(17) . . ? N6 C19 C18 115.09(15) . . ? C23 C19 C18 122.38(16) . . ? N6 C20 C21 122.93(18) . . ? N6 C20 H20 118.5 . . ? C21 C20 H20 118.5 . . ? C22 C21 C20 118.57(18) . . ? C22 C21 H21 120.7 . . ? C20 C21 H21 120.7 . . ? C21 C22 C23 119.26(18) . . ? C21 C22 H22 120.4 . . ? C23 C22 H22 120.4 . . ? C22 C23 C19 118.69(18) . . ? C22 C23 H23 120.7 . . ? C19 C23 H23 120.7 . . ? C4 N1 C3 120.75(15) . . ? C4 N1 Ni1 115.12(12) . . ? C3 N1 Ni1 120.77(11) . . ? C6 N2 C5 117.91(15) . . ? C6 N2 Ni1 129.82(12) . . ? C5 N2 Ni1 112.13(11) . . ? C11 N3 C10 120.19(16) . . ? C11 N3 Ni1 113.81(12) . . ? C10 N3 Ni1 120.02(11) . . ? C13 N4 C12 118.31(15) . . ? C13 N4 Ni1 128.87(13) . . ? C12 N4 Ni1 112.52(11) . . ? C18 N5 C17 120.71(15) . . ? C18 N5 Ni1 115.90(12) . . ? C17 N5 Ni1 121.27(11) . . ? C20 N6 C19 118.11(15) . . ? C20 N6 Ni1 129.08(12) . . ? C19 N6 Ni1 112.54(11) . . ? C1 O1 H1 109.5 . . ? O1M C1M H1M1 109.5 . . ? O1M C1M H1M2 109.5 . . ? H1M1 C1M H1M2 109.5 . . ? O1M C1M H1M3 109.5 . . ? H1M1 C1M H1M3 109.5 . . ? H1M2 C1M H1M3 109.5 . . ? C1M O1M H1M 109.5 . . ? O5 Cl1 O2 110.15(12) . . ? O5 Cl1 O3 111.30(11) . . ? O2 Cl1 O3 109.39(10) . . ? O5 Cl1 O4 108.39(11) . . ? O2 Cl1 O4 108.62(12) . . ? O3 Cl1 O4 108.94(11) . . ? O6 Cl2 O9 111.52(13) . . ? O6 Cl2 O8 109.27(13) . . ? O9 Cl2 O8 108.88(14) . . ? O6 Cl2 O7 109.27(11) . . ? O9 Cl2 O7 107.85(13) . . ? O8 Cl2 O7 110.03(12) . . ? O9A Cl2A O6 117.2(10) . . ? O9A Cl2A O7 123.8(10) . . ? O6 Cl2A O7 108.4(3) . . ? O9A Cl2A O8A 108.0(14) . . ? O6 Cl2A O8A 93.2(9) . . ? O7 Cl2A O8A 100.1(9) . . ? N1 Ni1 N5 85.84(6) . . ? N1 Ni1 N3 84.35(6) . . ? N5 Ni1 N3 84.10(6) . . ? N1 Ni1 N6 105.16(6) . . ? N5 Ni1 N6 78.74(6) . . ? N3 Ni1 N6 159.59(6) . . ? N1 Ni1 N2 79.20(6) . . ? N5 Ni1 N2 162.15(6) . . ? N3 Ni1 N2 103.87(6) . . ? N6 Ni1 N2 95.72(6) . . ? N1 Ni1 N4 159.98(6) . . ? N5 Ni1 N4 102.81(6) . . ? N3 Ni1 N4 78.72(6) . . ? N6 Ni1 N4 94.30(6) . . ? N2 Ni1 N4 94.47(6) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 54.1(2) . . . . ? O1 C1 C2 C10 173.71(16) . . . . ? O1 C1 C2 C17 -66.8(2) . . . . ? C1 C2 C3 N1 161.10(15) . . . . ? C10 C2 C3 N1 44.61(19) . . . . ? C17 C2 C3 N1 -79.95(18) . . . . ? N1 C4 C5 N2 -11.3(2) . . . . ? N1 C4 C5 C9 170.35(18) . . . . ? N2 C6 C7 C8 2.0(3) . . . . ? C6 C7 C8 C9 -1.0(3) . . . . ? N2 C5 C9 C8 1.4(3) . . . . ? C4 C5 C9 C8 179.61(18) . . . . ? C7 C8 C9 C5 -0.6(3) . . . . ? C1 C2 C10 N3 163.22(15) . . . . ? C3 C2 C10 N3 -79.05(18) . . . . ? C17 C2 C10 N3 45.61(19) . . . . ? N3 C11 C12 N4 -17.2(2) . . . . ? N3 C11 C12 C16 162.96(18) . . . . ? N4 C13 C14 C15 -0.2(3) . . . . ? C13 C14 C15 C16 1.2(3) . . . . ? C14 C15 C16 C12 -1.4(3) . . . . ? N4 C12 C16 C15 0.6(3) . . . . ? C11 C12 C16 C15 -179.56(18) . . . . ? C1 C2 C17 N5 165.71(15) . . . . ? C3 C2 C17 N5 46.71(19) . . . . ? C10 C2 C17 N5 -77.89(18) . . . . ? N5 C18 C19 N6 -9.4(2) . . . . ? N5 C18 C19 C23 174.38(17) . . . . ? N6 C20 C21 C22 0.5(3) . . . . ? C20 C21 C22 C23 0.6(3) . . . . ? C21 C22 C23 C19 -1.4(3) . . . . ? N6 C19 C23 C22 1.1(3) . . . . ? C18 C19 C23 C22 177.05(18) . . . . ? C5 C4 N1 C3 171.12(15) . . . . ? C5 C4 N1 Ni1 11.7(2) . . . . ? C2 C3 N1 C4 -127.08(18) . . . . ? C2 C3 N1 Ni1 31.23(19) . . . . ? C7 C6 N2 C5 -1.3(3) . . . . ? C7 C6 N2 Ni1 174.12(14) . . . . ? C9 C5 N2 C6 -0.5(3) . . . . ? C4 C5 N2 C6 -178.79(16) . . . . ? C9 C5 N2 Ni1 -176.65(15) . . . . ? C4 C5 N2 Ni1 5.02(19) . . . . ? C12 C11 N3 C10 171.85(15) . . . . ? C12 C11 N3 Ni1 19.0(2) . . . . ? C2 C10 N3 C11 -121.58(18) . . . . ? C2 C10 N3 Ni1 29.56(19) . . . . ? C14 C13 N4 C12 -0.5(2) . . . . ? C14 C13 N4 Ni1 172.63(13) . . . . ? C16 C12 N4 C13 0.3(3) . . . . ? C11 C12 N4 C13 -179.53(16) . . . . ? C16 C12 N4 Ni1 -173.92(14) . . . . ? C11 C12 N4 Ni1 6.27(19) . . . . ? C19 C18 N5 C17 168.06(15) . . . . ? C19 C18 N5 Ni1 4.4(2) . . . . ? C2 C17 N5 C18 -135.74(17) . . . . ? C2 C17 N5 Ni1 27.07(19) . . . . ? C21 C20 N6 C19 -0.8(3) . . . . ? C21 C20 N6 Ni1 172.61(14) . . . . ? C23 C19 N6 C20 0.1(3) . . . . ? C18 C19 N6 C20 -176.21(16) . . . . ? C23 C19 N6 Ni1 -174.45(14) . . . . ? C18 C19 N6 Ni1 9.29(18) . . . . ? Cl2A O6 Cl2 O9 49.0(3) . . . . ? Cl2A O6 Cl2 O8 169.4(3) . . . . ? Cl2A O6 Cl2 O7 -70.1(3) . . . . ? Cl2A O7 Cl2 O6 69.5(3) . . . . ? Cl2A O7 Cl2 O9 -51.9(3) . . . . ? Cl2A O7 Cl2 O8 -170.5(3) . . . . ? Cl2 O6 Cl2A O9A -145.8(12) . . . . ? Cl2 O6 Cl2A O7 68.1(3) . . . . ? Cl2 O6 Cl2A O8A -33.7(9) . . . . ? Cl2 O7 Cl2A O9A 148.3(13) . . . . ? Cl2 O7 Cl2A O6 -68.3(3) . . . . ? Cl2 O7 Cl2A O8A 28.5(9) . . . . ? C4 N1 Ni1 N5 -176.99(14) . . . . ? C3 N1 Ni1 N5 23.55(13) . . . . ? C4 N1 Ni1 N3 98.53(14) . . . . ? C3 N1 Ni1 N3 -60.93(13) . . . . ? C4 N1 Ni1 N6 -99.85(14) . . . . ? C3 N1 Ni1 N6 100.69(13) . . . . ? C4 N1 Ni1 N2 -6.79(13) . . . . ? C3 N1 Ni1 N2 -166.24(14) . . . . ? C4 N1 Ni1 N4 66.3(2) . . . . ? C3 N1 Ni1 N4 -93.2(2) . . . . ? C18 N5 Ni1 N1 106.87(14) . . . . ? C17 N5 Ni1 N1 -56.72(14) . . . . ? C18 N5 Ni1 N3 -168.39(14) . . . . ? C17 N5 Ni1 N3 28.02(13) . . . . ? C18 N5 Ni1 N6 0.50(13) . . . . ? C17 N5 Ni1 N6 -163.09(14) . . . . ? C18 N5 Ni1 N2 73.8(2) . . . . ? C17 N5 Ni1 N2 -89.7(2) . . . . ? C18 N5 Ni1 N4 -91.40(14) . . . . ? C17 N5 Ni1 N4 105.01(13) . . . . ? C11 N3 Ni1 N1 178.93(14) . . . . ? C10 N3 Ni1 N1 26.07(13) . . . . ? C11 N3 Ni1 N5 92.55(14) . . . . ? C10 N3 Ni1 N5 -60.32(13) . . . . ? C11 N3 Ni1 N6 59.7(2) . . . . ? C10 N3 Ni1 N6 -93.1(2) . . . . ? C11 N3 Ni1 N2 -103.68(14) . . . . ? C10 N3 Ni1 N2 103.46(13) . . . . ? C11 N3 Ni1 N4 -11.81(13) . . . . ? C10 N3 Ni1 N4 -164.67(14) . . . . ? C20 N6 Ni1 N1 98.22(16) . . . . ? C19 N6 Ni1 N1 -88.02(12) . . . . ? C20 N6 Ni1 N5 -179.28(17) . . . . ? C19 N6 Ni1 N5 -5.52(12) . . . . ? C20 N6 Ni1 N3 -145.95(17) . . . . ? C19 N6 Ni1 N3 27.8(2) . . . . ? C20 N6 Ni1 N2 17.89(16) . . . . ? C19 N6 Ni1 N2 -168.36(12) . . . . ? C20 N6 Ni1 N4 -77.05(16) . . . . ? C19 N6 Ni1 N4 96.70(12) . . . . ? C6 N2 Ni1 N1 -175.12(17) . . . . ? C5 N2 Ni1 N1 0.49(12) . . . . ? C6 N2 Ni1 N5 -141.53(19) . . . . ? C5 N2 Ni1 N5 34.1(3) . . . . ? C6 N2 Ni1 N3 103.52(16) . . . . ? C5 N2 Ni1 N3 -80.87(12) . . . . ? C6 N2 Ni1 N6 -70.74(16) . . . . ? C5 N2 Ni1 N6 104.87(12) . . . . ? C6 N2 Ni1 N4 24.05(16) . . . . ? C5 N2 Ni1 N4 -160.34(12) . . . . ? C13 N4 Ni1 N1 -138.25(17) . . . . ? C12 N4 Ni1 N1 35.2(2) . . . . ? C13 N4 Ni1 N5 107.73(15) . . . . ? C12 N4 Ni1 N5 -78.83(12) . . . . ? C13 N4 Ni1 N3 -171.06(15) . . . . ? C12 N4 Ni1 N3 2.38(11) . . . . ? C13 N4 Ni1 N6 28.31(15) . . . . ? C12 N4 Ni1 N6 -158.24(12) . . . . ? C13 N4 Ni1 N2 -67.78(15) . . . . ? C12 N4 Ni1 N2 105.66(12) . . . . ? 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 O1 H1 O1M 0.84 1.89 2.706(3) 164.5 3_566 O1M H1M O4 0.84 2.29 3.024(3) 146.8 1_554 O1M H1M O2 0.84 2.39 3.160(3) 153.2 1_554 O1M H1M Cl1 0.84 2.86 3.702(2) 176.5 1_554 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.02 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.851 _refine_diff_density_min -0.477 _refine_diff_density_rms 0.066 data_1_3 _database_code_depnum_ccdc_archive 'CCDC 845933' #TrackingRef 'combined_final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H24 Cl2 N6 O9 Zn' _chemical_formula_weight 664.75 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' 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 'P 21/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 9.6565(4) _cell_length_b 15.6786(9) _cell_length_c 17.5345(9) _cell_angle_alpha 90.00 _cell_angle_beta 93.361(3) _cell_angle_gamma 90.00 _cell_volume 2650.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 121538 _cell_measurement_theta_min 2.60 _cell_measurement_theta_max 25.68 _exptl_crystal_description parallelepiped _exptl_crystal_colour colourless _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.666 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1360 _exptl_absorpt_coefficient_mu 1.193 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.762 _exptl_absorpt_correction_T_max 0.920 _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 (617 frames)' _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 121538 _diffrn_reflns_av_R_equivalents 0.0178 _diffrn_reflns_av_sigmaI/netI 0.0258 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.60 _diffrn_reflns_theta_max 25.68 _reflns_number_total 5033 _reflns_number_gt 4284 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 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. One perchlorate ion is disordered over two positions sharing three O atoms, which have been refined with occupancy parameters of 0.5. The H atom bound to O1 was 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 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^)+(0.0588P)^2^+1.3949P] 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 5033 _refine_ls_number_parameters 388 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0435 _refine_ls_R_factor_gt 0.0357 _refine_ls_wR_factor_ref 0.0973 _refine_ls_wR_factor_gt 0.0930 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _refine_ls_shift/su_max 0.001 _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 1.161 _refine_diff_density_min -0.540 _refine_diff_density_rms 0.067 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 Zn Zn 0.12213(3) 0.165538(17) 0.215376(15) 0.02429(10) Uani 1 1 d . . . Cl1A Cl 0.2339(2) 0.63903(16) 0.53354(14) 0.0333(5) Uani 0.50 1 d P . . Cl1B Cl 0.2761(3) 0.65993(16) 0.55115(15) 0.0416(6) Uani 0.50 1 d P . . Cl2 Cl 0.35010(6) 0.95890(4) 0.63159(3) 0.03222(15) Uani 1 1 d . . . O1 O -0.3578(2) 0.17356(14) 0.02998(11) 0.0449(5) Uani 1 1 d . . . H1 H -0.4445 0.1638 0.0247 0.054 Uiso 1 1 d R . . O2A O 0.1233(4) 0.5856(3) 0.4994(2) 0.0549(11) Uani 0.50 1 d P . . O2B O 0.3946(7) 0.7124(4) 0.5703(3) 0.0788(17) Uani 0.50 1 d P . . O3 O 0.1880(3) 0.71813(18) 0.51077(14) 0.0826(10) Uani 1 1 d . . . O4 O 0.3449(3) 0.60413(18) 0.50442(13) 0.0758(9) Uani 1 1 d . . . O5 O 0.2319(2) 0.62983(14) 0.61843(11) 0.0469(5) Uani 1 1 d . . . O6 O 0.2385(2) 1.00103(17) 0.66606(13) 0.0634(7) Uani 1 1 d . . . O7 O 0.3019(3) 0.92546(14) 0.55848(12) 0.0554(6) Uani 1 1 d . . . O8 O 0.39829(18) 0.88950(13) 0.68049(11) 0.0410(5) Uani 1 1 d . . . O9 O 0.4609(2) 1.01762(13) 0.62123(13) 0.0492(5) Uani 1 1 d . . . N1 N -0.0284(2) 0.07490(13) 0.16628(11) 0.0277(4) Uani 1 1 d . . . N2 N 0.2472(2) 0.06128(13) 0.17886(11) 0.0267(4) Uani 1 1 d . . . N3 N -0.0635(2) 0.21464(13) 0.26314(11) 0.0264(4) Uani 1 1 d . . . N4 N 0.1538(2) 0.14059(13) 0.33612(11) 0.0258(4) Uani 1 1 d . . . N5 N 0.0454(2) 0.24013(14) 0.11959(11) 0.0282(4) Uani 1 1 d . . . N6 N 0.2777(2) 0.26545(13) 0.20774(11) 0.0271(4) Uani 1 1 d . . . C1 C -0.1949(2) 0.19254(17) 0.13899(14) 0.0295(5) Uani 1 1 d . . . C2 C -0.1759(2) 0.09606(17) 0.15300(14) 0.0301(5) Uani 1 1 d . . . H2A H -0.2257 0.0792 0.1970 0.036 Uiso 1 1 calc R . . H2B H -0.2143 0.0647 0.1090 0.036 Uiso 1 1 calc R . . C3 C 0.0247(3) 0.01368(16) 0.13021(14) 0.0289(5) Uani 1 1 d . . . H3 H -0.0301 -0.0205 0.0972 0.035 Uiso 1 1 calc R . . C4 C 0.1742(3) -0.00156(16) 0.14200(13) 0.0281(5) Uani 1 1 d . . . C5 C 0.2365(3) -0.07525(17) 0.11720(14) 0.0331(6) Uani 1 1 d . . . H5 H 0.1844 -0.1167 0.0906 0.040 Uiso 1 1 calc R . . C6 C 0.3783(3) -0.08639(18) 0.13269(15) 0.0379(6) Uani 1 1 d . . . H6 H 0.4220 -0.1360 0.1178 0.046 Uiso 1 1 calc R . . C7 C 0.4528(3) -0.02296(18) 0.17037(16) 0.0370(6) Uani 1 1 d . . . H7 H 0.5477 -0.0291 0.1814 0.044 Uiso 1 1 calc R . . C8 C 0.3845(3) 0.05029(17) 0.19163(14) 0.0312(5) Uani 1 1 d . . . H8 H 0.4360 0.0937 0.2158 0.037 Uiso 1 1 calc R . . C9 C -0.1827(2) 0.24374(17) 0.21455(14) 0.0291(5) Uani 1 1 d . . . H9A H -0.1723 0.3039 0.2033 0.035 Uiso 1 1 calc R . . H9B H -0.2669 0.2367 0.2415 0.035 Uiso 1 1 calc R . . C10 C -0.0792(2) 0.19328(15) 0.33219(13) 0.0266(5) Uani 1 1 d . . . H10 H -0.1637 0.2010 0.3542 0.032 Uiso 1 1 calc R . . C11 C 0.0410(2) 0.15591(15) 0.37614(14) 0.0261(5) Uani 1 1 d . . . C12 C 0.0366(3) 0.13611(17) 0.45265(14) 0.0326(6) Uani 1 1 d . . . H12 H -0.0429 0.1467 0.4786 0.039 Uiso 1 1 calc R . . C13 C 0.1529(3) 0.10011(17) 0.49024(14) 0.0335(6) Uani 1 1 d . . . H13 H 0.1519 0.0853 0.5416 0.040 Uiso 1 1 calc R . . C14 C 0.2703(3) 0.08654(16) 0.45042(14) 0.0305(5) Uani 1 1 d . . . H14 H 0.3505 0.0643 0.4748 0.037 Uiso 1 1 calc R . . C15 C 0.2659(2) 0.10684(15) 0.37350(14) 0.0284(5) Uani 1 1 d . . . H15 H 0.3443 0.0966 0.3465 0.034 Uiso 1 1 calc R . . C16 C -0.0920(3) 0.22609(18) 0.08130(14) 0.0322(6) Uani 1 1 d . . . H16A H -0.0846 0.1850 0.0404 0.039 Uiso 1 1 calc R . . H16B H -0.1265 0.2792 0.0591 0.039 Uiso 1 1 calc R . . C17 C 0.1180(3) 0.30369(16) 0.10308(14) 0.0290(5) Uani 1 1 d . . . H17 H 0.0898 0.3399 0.0631 0.035 Uiso 1 1 calc R . . C18 C 0.2491(3) 0.31916(15) 0.14875(15) 0.0290(5) Uani 1 1 d . . . C19 C 0.3337(3) 0.38768(16) 0.13329(16) 0.0348(6) Uani 1 1 d . . . H19 H 0.3122 0.4230 0.0917 0.042 Uiso 1 1 calc R . . C20 C 0.4510(3) 0.40266(17) 0.18084(16) 0.0375(6) Uani 1 1 d . . . H20 H 0.5087 0.4487 0.1720 0.045 Uiso 1 1 calc R . . C21 C 0.4809(3) 0.34822(17) 0.24158(16) 0.0346(6) Uani 1 1 d . . . H21 H 0.5591 0.3569 0.2742 0.041 Uiso 1 1 calc R . . C22 C 0.3922(3) 0.28027(16) 0.25303(15) 0.0304(5) Uani 1 1 d . . . H22 H 0.4129 0.2435 0.2937 0.036 Uiso 1 1 calc R . . C23 C -0.3431(3) 0.2074(2) 0.10519(15) 0.0359(6) Uani 1 1 d . . . H23A H -0.4087 0.1801 0.1371 0.043 Uiso 1 1 calc R . . H23B H -0.3629 0.2681 0.1039 0.043 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 Zn 0.02294(16) 0.02648(16) 0.02354(16) 0.00047(11) 0.00219(11) -0.00052(10) Cl1A 0.0370(11) 0.0307(12) 0.0329(11) 0.0014(8) 0.0089(8) 0.0061(8) Cl1B 0.0563(16) 0.0315(12) 0.0388(13) 0.0041(9) 0.0189(10) 0.0134(10) Cl2 0.0252(3) 0.0398(4) 0.0317(3) 0.0078(3) 0.0021(2) 0.0026(2) O1 0.0320(10) 0.0704(15) 0.0315(10) -0.0057(9) -0.0064(8) 0.0035(9) O2A 0.048(2) 0.067(3) 0.050(3) -0.017(2) 0.007(2) -0.005(2) O2B 0.108(5) 0.083(4) 0.047(3) 0.004(3) 0.013(3) -0.045(4) O3 0.115(2) 0.0800(19) 0.0551(15) 0.0212(14) 0.0252(15) 0.0694(18) O4 0.108(2) 0.0839(19) 0.0364(12) 0.0036(12) 0.0098(13) 0.0659(17) O5 0.0486(12) 0.0539(13) 0.0391(11) 0.0076(10) 0.0106(9) 0.0050(10) O6 0.0515(13) 0.0877(18) 0.0533(14) 0.0187(13) 0.0216(11) 0.0357(13) O7 0.0808(16) 0.0467(13) 0.0368(11) 0.0066(10) -0.0115(11) -0.0087(11) O8 0.0304(10) 0.0460(12) 0.0455(11) 0.0184(9) -0.0060(8) -0.0006(8) O9 0.0373(11) 0.0423(12) 0.0676(14) 0.0169(10) -0.0009(10) -0.0069(9) N1 0.0262(10) 0.0308(11) 0.0261(10) 0.0009(9) 0.0029(8) -0.0019(8) N2 0.0286(10) 0.0291(11) 0.0227(10) -0.0001(8) 0.0035(8) -0.0008(8) N3 0.0253(10) 0.0280(11) 0.0258(10) -0.0008(8) 0.0013(8) 0.0013(8) N4 0.0262(10) 0.0255(10) 0.0258(10) 0.0001(8) 0.0016(8) -0.0005(8) N5 0.0260(10) 0.0338(12) 0.0253(10) 0.0014(9) 0.0051(8) 0.0018(9) N6 0.0268(10) 0.0265(10) 0.0283(11) -0.0034(8) 0.0044(8) 0.0005(8) C1 0.0254(12) 0.0383(14) 0.0245(12) 0.0006(10) 0.0002(10) 0.0008(10) C2 0.0222(11) 0.0387(14) 0.0291(13) -0.0009(11) 0.0003(10) -0.0016(10) C3 0.0304(13) 0.0313(13) 0.0250(12) -0.0004(10) 0.0024(10) -0.0052(10) C4 0.0323(13) 0.0299(13) 0.0223(11) 0.0007(10) 0.0053(10) -0.0017(10) C5 0.0378(14) 0.0314(14) 0.0303(13) -0.0035(11) 0.0046(11) -0.0011(11) C6 0.0421(15) 0.0348(15) 0.0373(15) -0.0027(11) 0.0067(12) 0.0093(12) C7 0.0294(13) 0.0423(16) 0.0396(15) -0.0013(12) 0.0039(11) 0.0062(11) C8 0.0276(12) 0.0352(14) 0.0309(13) -0.0011(11) 0.0025(10) 0.0000(10) C9 0.0245(12) 0.0355(14) 0.0274(12) 0.0018(10) 0.0011(9) 0.0038(10) C10 0.0246(12) 0.0276(12) 0.0277(12) -0.0032(10) 0.0025(9) -0.0003(10) C11 0.0262(12) 0.0263(12) 0.0258(12) -0.0036(9) 0.0016(10) -0.0009(9) C12 0.0339(14) 0.0366(14) 0.0278(13) -0.0007(11) 0.0062(11) 0.0038(11) C13 0.0422(15) 0.0359(14) 0.0222(12) -0.0007(10) -0.0001(11) 0.0071(11) C14 0.0339(13) 0.0283(13) 0.0286(13) -0.0024(10) -0.0040(10) 0.0018(10) C15 0.0266(12) 0.0284(13) 0.0301(13) 0.0004(10) 0.0016(10) 0.0002(10) C16 0.0274(12) 0.0420(15) 0.0269(12) 0.0055(11) 0.0002(10) 0.0016(11) C17 0.0315(13) 0.0281(13) 0.0281(13) 0.0028(10) 0.0067(10) 0.0037(10) C18 0.0312(13) 0.0249(12) 0.0316(13) -0.0021(10) 0.0096(10) 0.0035(10) C19 0.0367(14) 0.0266(13) 0.0424(15) 0.0002(11) 0.0135(12) -0.0004(11) C20 0.0354(14) 0.0287(13) 0.0499(17) -0.0069(12) 0.0154(12) -0.0060(11) C21 0.0275(13) 0.0339(14) 0.0429(15) -0.0120(12) 0.0071(11) -0.0009(10) C22 0.0305(13) 0.0286(13) 0.0323(13) -0.0054(10) 0.0045(10) 0.0002(10) C23 0.0275(13) 0.0516(17) 0.0283(13) -0.0001(12) -0.0005(10) 0.0016(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 Zn N5 2.143(2) . ? Zn N2 2.152(2) . ? Zn N4 2.157(2) . ? Zn N3 2.164(2) . ? Zn N1 2.174(2) . ? Zn N6 2.180(2) . ? Cl1A O4 1.332(3) . ? Cl1A O3 1.369(4) . ? Cl1A O2A 1.458(5) . ? Cl1A O5 1.497(3) . ? Cl1B O5 1.362(3) . ? Cl1B O4 1.394(3) . ? Cl1B O3 1.410(4) . ? Cl1B O2B 1.433(6) . ? Cl2 O6 1.428(2) . ? Cl2 O9 1.431(2) . ? Cl2 O7 1.437(2) . ? Cl2 O8 1.4453(19) . ? O1 C23 1.421(3) . ? O1 H1 0.8509 . ? N1 C3 1.273(3) . ? N1 C2 1.468(3) . ? N2 C8 1.343(3) . ? N2 C4 1.354(3) . ? N3 C10 1.274(3) . ? N3 C9 1.464(3) . ? N4 C15 1.341(3) . ? N4 C11 1.352(3) . ? N5 C17 1.262(3) . ? N5 C16 1.468(3) . ? N6 C22 1.344(3) . ? N6 C18 1.350(3) . ? C1 C23 1.534(3) . ? C1 C2 1.542(4) . ? C1 C9 1.548(3) . ? C1 C16 1.551(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.466(3) . ? C3 H3 0.9300 . ? C4 C5 1.385(4) . ? C5 C6 1.391(4) . ? C5 H5 0.9300 . ? C6 C7 1.374(4) . ? C6 H6 0.9300 . ? C7 C8 1.386(4) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.477(3) . ? C10 H10 0.9300 . ? C11 C12 1.380(3) . ? C12 C13 1.388(4) . ? C12 H12 0.9300 . ? C13 C14 1.382(4) . ? C13 H13 0.9300 . ? C14 C15 1.384(3) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.478(4) . ? C17 H17 0.9300 . ? C18 C19 1.386(4) . ? C19 C20 1.386(4) . ? C19 H19 0.9300 . ? C20 C21 1.382(4) . ? C20 H20 0.9300 . ? C21 C22 1.389(4) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? 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 N5 Zn N2 110.83(7) . . ? N5 Zn N4 152.99(8) . . ? N2 Zn N4 96.00(7) . . ? N5 Zn N3 81.55(7) . . ? N2 Zn N3 151.33(8) . . ? N4 Zn N3 75.98(7) . . ? N5 Zn N1 81.60(8) . . ? N2 Zn N1 76.09(8) . . ? N4 Zn N1 108.86(7) . . ? N3 Zn N1 80.57(7) . . ? N5 Zn N6 76.55(8) . . ? N2 Zn N6 97.29(7) . . ? N4 Zn N6 97.59(7) . . ? N3 Zn N6 110.94(7) . . ? N1 Zn N6 153.19(8) . . ? O4 Cl1A O3 121.0(3) . . ? O4 Cl1A O2A 101.1(3) . . ? O3 Cl1A O2A 100.6(3) . . ? O4 Cl1A O5 113.5(2) . . ? O3 Cl1A O5 110.8(2) . . ? O2A Cl1A O5 107.5(3) . . ? O5 Cl1B O4 118.4(2) . . ? O5 Cl1B O3 116.7(2) . . ? O4 Cl1B O3 113.9(2) . . ? O5 Cl1B O2B 106.4(3) . . ? O4 Cl1B O2B 95.5(3) . . ? O3 Cl1B O2B 101.3(3) . . ? O6 Cl2 O9 110.13(15) . . ? O6 Cl2 O7 109.47(15) . . ? O9 Cl2 O7 109.09(14) . . ? O6 Cl2 O8 108.78(13) . . ? O9 Cl2 O8 110.04(12) . . ? O7 Cl2 O8 109.32(13) . . ? C23 O1 H1 102.3 . . ? C3 N1 C2 120.4(2) . . ? C3 N1 Zn 114.23(16) . . ? C2 N1 Zn 122.35(16) . . ? C8 N2 C4 117.9(2) . . ? C8 N2 Zn 127.87(17) . . ? C4 N2 Zn 114.16(16) . . ? C10 N3 C9 120.1(2) . . ? C10 N3 Zn 114.97(16) . . ? C9 N3 Zn 121.76(15) . . ? C15 N4 C11 117.9(2) . . ? C15 N4 Zn 127.98(16) . . ? C11 N4 Zn 113.89(15) . . ? C17 N5 C16 120.9(2) . . ? C17 N5 Zn 116.07(17) . . ? C16 N5 Zn 122.58(16) . . ? C22 N6 C18 118.0(2) . . ? C22 N6 Zn 129.36(17) . . ? C18 N6 Zn 112.65(16) . . ? C23 C1 C2 108.1(2) . . ? C23 C1 C9 105.9(2) . . ? C2 C1 C9 111.7(2) . . ? C23 C1 C16 108.4(2) . . ? C2 C1 C16 111.2(2) . . ? C9 C1 C16 111.3(2) . . ? N1 C2 C1 110.6(2) . . ? N1 C2 H2A 109.5 . . ? C1 C2 H2A 109.5 . . ? N1 C2 H2B 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 108.1 . . ? N1 C3 C4 118.3(2) . . ? N1 C3 H3 120.8 . . ? C4 C3 H3 120.8 . . ? N2 C4 C5 122.2(2) . . ? N2 C4 C3 115.5(2) . . ? C5 C4 C3 122.3(2) . . ? C4 C5 C6 119.0(2) . . ? C4 C5 H5 120.5 . . ? C6 C5 H5 120.5 . . ? C7 C6 C5 119.0(2) . . ? C7 C6 H6 120.5 . . ? C5 C6 H6 120.5 . . ? C6 C7 C8 119.0(2) . . ? C6 C7 H7 120.5 . . ? C8 C7 H7 120.5 . . ? N2 C8 C7 122.9(2) . . ? N2 C8 H8 118.6 . . ? C7 C8 H8 118.6 . . ? N3 C9 C1 110.7(2) . . ? N3 C9 H9A 109.5 . . ? C1 C9 H9A 109.5 . . ? N3 C9 H9B 109.5 . . ? C1 C9 H9B 109.5 . . ? H9A C9 H9B 108.1 . . ? N3 C10 C11 117.8(2) . . ? N3 C10 H10 121.1 . . ? C11 C10 H10 121.1 . . ? N4 C11 C12 122.4(2) . . ? N4 C11 C10 115.6(2) . . ? C12 C11 C10 121.9(2) . . ? C11 C12 C13 118.9(2) . . ? C11 C12 H12 120.6 . . ? C13 C12 H12 120.6 . . ? C14 C13 C12 119.2(2) . . ? C14 C13 H13 120.4 . . ? C12 C13 H13 120.4 . . ? C13 C14 C15 118.5(2) . . ? C13 C14 H14 120.7 . . ? C15 C14 H14 120.7 . . ? N4 C15 C14 123.0(2) . . ? N4 C15 H15 118.5 . . ? C14 C15 H15 118.5 . . ? N5 C16 C1 110.41(19) . . ? N5 C16 H16A 109.6 . . ? C1 C16 H16A 109.6 . . ? N5 C16 H16B 109.6 . . ? C1 C16 H16B 109.6 . . ? H16A C16 H16B 108.1 . . ? N5 C17 C18 118.4(2) . . ? N5 C17 H17 120.8 . . ? C18 C17 H17 120.8 . . ? N6 C18 C19 122.5(2) . . ? N6 C18 C17 116.3(2) . . ? C19 C18 C17 121.1(2) . . ? C18 C19 C20 118.9(3) . . ? C18 C19 H19 120.5 . . ? C20 C19 H19 120.5 . . ? C21 C20 C19 119.0(2) . . ? C21 C20 H20 120.5 . . ? C19 C20 H20 120.5 . . ? C20 C21 C22 118.8(3) . . ? C20 C21 H21 120.6 . . ? C22 C21 H21 120.6 . . ? N6 C22 C21 122.7(2) . . ? N6 C22 H22 118.6 . . ? C21 C22 H22 118.6 . . ? O1 C23 C1 110.0(2) . . ? O1 C23 H23A 109.7 . . ? C1 C23 H23A 109.7 . . ? O1 C23 H23B 109.7 . . ? C1 C23 H23B 109.7 . . ? H23A C23 H23B 108.2 . . ? 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 O1 H1 O2A 0.85 2.14 2.931(5) 154.5 2_445 data_1_4 _database_code_depnum_ccdc_archive 'CCDC 845934' #TrackingRef 'combined_final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H24 N6 O1 Zn, 2(Cl O4)' _chemical_formula_sum 'C23 H24 Cl2 N6 O9 Zn' _chemical_formula_weight 664.75 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' 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 P21/n _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 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 9.6750(3) _cell_length_b 15.5878(5) _cell_length_c 17.8081(6) _cell_angle_alpha 90.00 _cell_angle_beta 93.557(2) _cell_angle_gamma 90.00 _cell_volume 2680.50(15) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 7106 _cell_measurement_theta_min 2.638 _cell_measurement_theta_max 27.672 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.060 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.647 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1360 _exptl_absorpt_coefficient_mu 1.180 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.820 _exptl_absorpt_correction_T_max 0.932 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2001)' _exptl_special_details ; The crystal was coated in Exxon Paratone N hydrocarbon oil and mounted on a thin mohair fibre attached to a copper pin. Upon mounting on the diffractometer, the crystal was quenched to 150(K) under a cold nitrogen gas stream supplied by an Oxford Cryosystems Cryostream and data were collected at this temperature. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type APEXII-FR591 _diffrn_measurement_method \w+\f _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 79074 _diffrn_reflns_av_R_equivalents 0.0416 _diffrn_reflns_av_sigmaI/netI 0.0233 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.29 _diffrn_reflns_theta_max 28.27 _reflns_number_total 6624 _reflns_number_gt 5170 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX (Bruker-Nonius, 2003)' _computing_cell_refinement 'SAINT (Bruker-Nonius, 2003)' _computing_data_reduction 'SAINT (Bruker-Nonius, 2003), XPREP (Bruker-Nonius, 2003)' _computing_structure_solution 'SIR97 (Altomare, et. al. 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ;ORTEP-3 (Farrugia, 1997) WINGX-32 (Farrugia, 1999) ; _computing_publication_material 'enCIFer 1.1 (CCDC, 2005)' _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^)+(0.0583P)^2^+2.1430P] 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 6624 _refine_ls_number_parameters 421 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0585 _refine_ls_R_factor_gt 0.0403 _refine_ls_wR_factor_ref 0.1144 _refine_ls_wR_factor_gt 0.1027 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.1578(3) 0.2100(2) 0.60595(16) 0.0459(7) Uani 1 1 d D . . H1A H 0.0903 0.1828 0.6381 0.055 Uiso 1 1 calc R . . H1B H 0.1390 0.2724 0.6043 0.055 Uiso 1 1 calc R . . C2 C 0.3063(2) 0.19389(18) 0.63968(14) 0.0359(5) Uani 1 1 d . . . C3 C 0.3191(2) 0.24472(18) 0.71435(14) 0.0374(5) Uani 1 1 d . . . H3A H 0.3308 0.3065 0.7035 0.045 Uiso 1 1 calc R . . H3B H 0.2332 0.2378 0.7412 0.045 Uiso 1 1 calc R . . C4 C 0.4219(2) 0.19324(16) 0.83008(14) 0.0343(5) Uani 1 1 d . . . H4 H 0.3358 0.2013 0.8520 0.041 Uiso 1 1 calc R . . C5 C 0.5422(2) 0.15572(15) 0.87391(14) 0.0330(5) Uani 1 1 d . . . C6 C 0.7660(3) 0.10530(17) 0.87230(15) 0.0388(6) Uani 1 1 d . . . H6 H 0.8459 0.0941 0.8455 0.047 Uiso 1 1 calc R . . C7 C 0.7699(3) 0.08596(18) 0.94809(15) 0.0423(6) Uani 1 1 d . . . H7 H 0.8516 0.0633 0.9730 0.051 Uiso 1 1 calc R . . C8 C 0.6534(3) 0.1001(2) 0.98697(15) 0.0461(7) Uani 1 1 d . . . H8 H 0.6523 0.0851 1.0386 0.055 Uiso 1 1 calc R . . C9 C 0.5372(3) 0.13658(19) 0.94963(15) 0.0440(6) Uani 1 1 d . . . H9 H 0.4563 0.1481 0.9755 0.053 Uiso 1 1 calc R . . C10 C 0.4097(3) 0.22735(19) 0.58308(15) 0.0406(6) Uani 1 1 d . . . H10A H 0.4157 0.1855 0.5416 0.049 Uiso 1 1 calc R . . H10B H 0.3755 0.2823 0.5612 0.049 Uiso 1 1 calc R . . C11 C 0.6208(3) 0.30426(18) 0.60510(16) 0.0427(6) Uani 1 1 d . . . H11 H 0.5921 0.3423 0.5655 0.051 Uiso 1 1 calc R . . C12 C 0.7519(3) 0.31860(16) 0.65032(17) 0.0397(6) Uani 1 1 d . . . C13 C 0.8916(3) 0.27971(18) 0.75389(17) 0.0433(6) Uani 1 1 d . . . H13 H 0.9113 0.2424 0.7953 0.052 Uiso 1 1 calc R . . C14 C 0.9823(3) 0.3476(2) 0.7425(2) 0.0542(8) Uani 1 1 d . . . H14 H 1.0617 0.3564 0.7757 0.065 Uiso 1 1 calc R . . C15 C 0.9548(3) 0.4011(2) 0.6825(2) 0.0594(9) Uani 1 1 d . . . H15 H 1.0148 0.4477 0.6735 0.071 Uiso 1 1 calc R . . C16 C 0.8390(3) 0.38657(19) 0.6356(2) 0.0534(8) Uani 1 1 d . . . H16 H 0.8187 0.4227 0.5934 0.064 Uiso 1 1 calc R . . C17 C 0.3237(2) 0.09668(18) 0.65276(15) 0.0388(6) Uani 1 1 d . . . H17A H 0.2731 0.0793 0.6969 0.047 Uiso 1 1 calc R . . H17B H 0.2839 0.0651 0.6083 0.047 Uiso 1 1 calc R . . C18 C 0.5241(3) 0.01399(17) 0.62954(15) 0.0370(5) Uani 1 1 d . . . H18 H 0.4681 -0.0206 0.5959 0.044 Uiso 1 1 calc R . . C19 C 0.6737(3) -0.00176(17) 0.64085(14) 0.0353(5) Uani 1 1 d . . . C20 C 0.8837(3) 0.04878(19) 0.69074(16) 0.0410(6) Uani 1 1 d . . . H20 H 0.9365 0.0927 0.7160 0.049 Uiso 1 1 calc R . . C21 C 0.9520(3) -0.0241(2) 0.66795(18) 0.0503(7) Uani 1 1 d . . . H21 H 1.0488 -0.0305 0.6787 0.060 Uiso 1 1 calc R . . C22 C 0.8768(3) -0.0867(2) 0.62957(17) 0.0509(7) Uani 1 1 d . . . H22 H 0.9212 -0.1372 0.6133 0.061 Uiso 1 1 calc R . . C23 C 0.7360(3) -0.07558(18) 0.61486(16) 0.0448(6) Uani 1 1 d . . . H23 H 0.6827 -0.1176 0.5875 0.054 Uiso 1 1 calc R . . N1 N 0.4377(2) 0.21424(13) 0.76229(11) 0.0332(4) Uani 1 1 d . . . N2 N 0.6543(2) 0.13917(13) 0.83488(11) 0.0327(4) Uani 1 1 d . . . N3 N 0.5477(2) 0.24015(15) 0.62039(12) 0.0388(5) Uani 1 1 d . . . N4 N 0.7780(2) 0.26511(13) 0.70887(12) 0.0350(4) Uani 1 1 d . . . N5 N 0.4711(2) 0.07471(14) 0.66567(12) 0.0345(4) Uani 1 1 d . . . N6 N 0.7467(2) 0.06013(13) 0.67885(11) 0.0325(4) Uani 1 1 d . . . O1 O 0.1421(2) 0.17571(17) 0.53264(12) 0.0614(6) Uani 1 1 d D . . H1O H 0.0639(18) 0.162(3) 0.5100(12) 0.092 Uiso 1 1 d D . . O2 O 0.1038(2) 0.10672(15) 0.81748(13) 0.0567(6) Uani 1 1 d . A . O3 O 0.0386(6) -0.0155(4) 0.8849(5) 0.0597(15) Uani 0.60 1 d P A 1 O4 O 0.1785(6) 0.0761(3) 0.9418(2) 0.0625(12) Uani 0.60 1 d P A 1 O5 O 0.2724(5) 0.0053(4) 0.8402(3) 0.0677(15) Uani 0.60 1 d P A 1 O3A O 0.2308(10) 0.0618(7) 0.9289(6) 0.087(3) Uiso 0.40 1 d P A 2 O4A O 0.0503(14) -0.0277(9) 0.8636(7) 0.070(4) Uiso 0.40 1 d P A 2 O5A O 0.2346(14) -0.0223(9) 0.8271(8) 0.111(5) Uiso 0.40 1 d P A 2 O8 O 0.7682(3) 0.13109(18) 0.38422(14) 0.0695(7) Uani 1 1 d . . . O7 O 0.6377(8) 0.1133(8) 0.4926(6) 0.059(3) Uani 0.50 1 d P B 2 O9A O 0.8750(6) 0.0874(5) 0.5011(4) 0.101(2) Uani 0.50 1 d P B 2 O6A O 0.7893(9) 0.2277(6) 0.4846(5) 0.083(3) Uani 0.50 1 d P B 2 O9 O 0.8377(9) 0.2028(8) 0.4969(7) 0.101(4) Uani 0.50 1 d P C 1 O6 O 0.6095(9) 0.2130(5) 0.4309(4) 0.117(3) Uani 0.50 1 d P C 1 O7A O 0.6818(13) 0.0935(9) 0.4963(7) 0.112(5) Uani 0.50 1 d P C 1 Cl1 Cl 0.15033(6) 0.03790(5) 0.86657(4) 0.04551(17) Uani 1 1 d . . . Cl2 Cl 0.7274(5) 0.1619(3) 0.4520(3) 0.0701(13) Uani 0.50 1 d P C 1 Cl2A Cl 0.7612(4) 0.1403(3) 0.4646(3) 0.0489(7) Uani 0.50 1 d P B 2 Zn1 Zn 0.62262(3) 0.165023(18) 0.715767(15) 0.02985(9) 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 C1 0.0275(12) 0.0677(19) 0.0421(14) 0.0031(13) -0.0021(10) 0.0072(12) C2 0.0235(11) 0.0470(14) 0.0370(13) 0.0046(11) 0.0010(9) 0.0038(10) C3 0.0252(11) 0.0455(15) 0.0415(13) 0.0007(11) 0.0036(9) 0.0068(10) C4 0.0280(11) 0.0384(13) 0.0367(13) -0.0053(10) 0.0035(9) 0.0012(10) C5 0.0301(11) 0.0329(12) 0.0359(12) -0.0064(10) 0.0016(9) -0.0010(9) C6 0.0289(12) 0.0439(15) 0.0434(14) 0.0004(11) 0.0005(10) 0.0023(10) C7 0.0391(14) 0.0437(15) 0.0429(14) -0.0028(12) -0.0079(11) 0.0048(11) C8 0.0523(16) 0.0554(17) 0.0298(13) -0.0043(12) -0.0020(11) 0.0107(13) C9 0.0432(15) 0.0540(17) 0.0352(13) -0.0030(12) 0.0047(11) 0.0086(13) C10 0.0291(12) 0.0552(16) 0.0378(13) 0.0105(12) 0.0034(10) 0.0029(11) C11 0.0396(14) 0.0382(14) 0.0517(16) 0.0099(12) 0.0128(12) 0.0065(11) C12 0.0338(12) 0.0298(12) 0.0570(16) -0.0012(11) 0.0162(11) 0.0028(10) C13 0.0323(13) 0.0397(14) 0.0586(17) -0.0137(13) 0.0078(11) 0.0001(11) C14 0.0318(13) 0.0489(17) 0.083(2) -0.0299(17) 0.0134(14) -0.0053(12) C15 0.0463(17) 0.0389(16) 0.096(3) -0.0137(17) 0.0312(17) -0.0109(13) C16 0.0507(17) 0.0335(14) 0.079(2) 0.0031(14) 0.0256(15) -0.0023(12) C17 0.0270(11) 0.0471(15) 0.0426(14) -0.0006(11) 0.0031(10) -0.0021(10) C18 0.0345(12) 0.0384(14) 0.0381(13) -0.0013(11) 0.0033(10) -0.0055(10) C19 0.0354(12) 0.0366(13) 0.0346(12) 0.0016(10) 0.0074(10) -0.0035(10) C20 0.0301(12) 0.0453(15) 0.0482(15) -0.0013(12) 0.0061(11) 0.0013(11) C21 0.0338(14) 0.0558(18) 0.0618(18) -0.0029(14) 0.0072(13) 0.0094(12) C22 0.0521(17) 0.0461(16) 0.0556(17) -0.0031(13) 0.0123(14) 0.0133(13) C23 0.0501(16) 0.0394(15) 0.0454(15) -0.0065(12) 0.0082(12) -0.0031(12) N1 0.0259(9) 0.0374(11) 0.0362(11) -0.0025(9) 0.0027(8) 0.0026(8) N2 0.0259(9) 0.0358(11) 0.0364(11) -0.0009(8) 0.0019(8) 0.0009(8) N3 0.0301(10) 0.0441(12) 0.0428(12) 0.0071(10) 0.0070(9) 0.0022(9) N4 0.0261(9) 0.0315(10) 0.0480(12) -0.0059(9) 0.0080(8) -0.0018(8) N5 0.0283(10) 0.0389(11) 0.0366(11) 0.0032(9) 0.0038(8) -0.0012(8) N6 0.0291(10) 0.0346(11) 0.0341(10) 0.0006(8) 0.0051(8) 0.0001(8) O1 0.0389(11) 0.0967(19) 0.0471(12) -0.0053(12) -0.0095(9) 0.0055(12) O2 0.0375(10) 0.0641(14) 0.0672(14) 0.0240(11) -0.0074(9) -0.0011(10) O3 0.042(2) 0.055(3) 0.083(5) 0.021(3) 0.012(3) -0.007(2) O4 0.090(4) 0.062(3) 0.037(2) -0.0020(17) 0.008(2) 0.018(2) O5 0.039(2) 0.087(4) 0.080(3) 0.023(3) 0.029(2) 0.035(3) O8 0.0669(15) 0.0754(17) 0.0680(15) -0.0068(13) 0.0193(12) -0.0058(13) O7 0.041(3) 0.090(6) 0.047(4) -0.020(4) 0.014(3) -0.024(3) O9A 0.070(4) 0.140(6) 0.093(4) 0.053(4) 0.011(3) 0.020(4) O6A 0.113(7) 0.069(5) 0.071(4) -0.021(3) 0.048(5) -0.062(5) O9 0.049(4) 0.105(8) 0.146(8) -0.033(6) -0.025(4) -0.024(4) O6 0.144(7) 0.125(6) 0.086(4) 0.004(4) 0.033(4) 0.067(5) O7A 0.167(12) 0.101(8) 0.064(5) 0.035(5) -0.024(7) -0.090(9) Cl1 0.0280(3) 0.0570(4) 0.0514(4) 0.0129(3) 0.0010(3) 0.0032(3) Cl2 0.086(3) 0.046(2) 0.084(3) -0.0081(16) 0.045(2) -0.0200(17) Cl2A 0.0474(14) 0.046(2) 0.0546(13) -0.0051(13) 0.0169(10) -0.0182(12) Zn1 0.02212(14) 0.03178(16) 0.03594(16) 0.00035(11) 0.00414(10) -0.00117(10) _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 C1 O1 1.410(4) . ? C1 C2 1.543(3) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C17 1.541(4) . ? C2 C3 1.546(4) . ? C2 C10 1.553(3) . ? C3 N1 1.466(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 N1 1.269(3) . ? C4 C5 1.481(3) . ? C4 H4 0.9500 . ? C5 N2 1.348(3) . ? C5 C9 1.385(4) . ? C6 N2 1.342(3) . ? C6 C7 1.381(4) . ? C6 H6 0.9500 . ? C7 C8 1.377(4) . ? C7 H7 0.9500 . ? C8 C9 1.391(4) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 N3 1.468(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 N3 1.264(3) . ? C11 C12 1.477(4) . ? C11 H11 0.9500 . ? C12 N4 1.347(4) . ? C12 C16 1.389(4) . ? C13 N4 1.339(3) . ? C13 C14 1.398(4) . ? C13 H13 0.9500 . ? C14 C15 1.367(5) . ? C14 H14 0.9500 . ? C15 C16 1.374(5) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 N5 1.470(3) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 N5 1.270(3) . ? C18 C19 1.469(4) . ? C18 H18 0.9500 . ? C19 N6 1.352(3) . ? C19 C23 1.392(4) . ? C20 N6 1.341(3) . ? C20 C21 1.387(4) . ? C20 H20 0.9500 . ? C21 C22 1.374(4) . ? C21 H21 0.9500 . ? C22 C23 1.382(4) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? N1 Zn1 2.1587(19) . ? N2 Zn1 2.162(2) . ? N3 Zn1 2.152(2) . ? N4 Zn1 2.175(2) . ? N5 Zn1 2.183(2) . ? N6 Zn1 2.155(2) . ? O1 H1O 0.861(10) . ? O2 Cl1 1.438(2) . ? O3 Cl1 1.418(6) . ? O4 Cl1 1.476(4) . ? O5 Cl1 1.394(4) . ? O3A Cl1 1.368(11) . ? O4A Cl1 1.406(14) . ? O5A Cl1 1.452(14) . ? O8 Cl2 1.380(7) . ? O8 Cl2A 1.444(6) . ? O7 Cl2A 1.388(10) . ? O9A Cl2A 1.492(7) . ? O6A Cl2A 1.430(10) . ? O9 Cl2 1.442(11) . ? O6 Cl2 1.423(8) . ? O7A Cl2 1.413(13) . ? 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 C1 C2 110.1(2) . . ? O1 C1 H1A 109.6 . . ? C2 C1 H1A 109.7 . . ? O1 C1 H1B 109.6 . . ? C2 C1 H1B 109.6 . . ? H1A C1 H1B 108.2 . . ? C17 C2 C1 108.0(2) . . ? C17 C2 C3 111.8(2) . . ? C1 C2 C3 105.9(2) . . ? C17 C2 C10 111.1(2) . . ? C1 C2 C10 108.3(2) . . ? C3 C2 C10 111.4(2) . . ? N1 C3 C2 110.6(2) . . ? N1 C3 H3A 109.5 . . ? C2 C3 H3A 109.5 . . ? N1 C3 H3B 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 108.1 . . ? N1 C4 C5 117.8(2) . . ? N1 C4 H4 121.1 . . ? C5 C4 H4 121.1 . . ? N2 C5 C9 122.6(2) . . ? N2 C5 C4 115.8(2) . . ? C9 C5 C4 121.6(2) . . ? N2 C6 C7 122.9(2) . . ? N2 C6 H6 118.5 . . ? C7 C6 H6 118.5 . . ? C8 C7 C6 118.9(2) . . ? C8 C7 H7 120.6 . . ? C6 C7 H7 120.6 . . ? C7 C8 C9 119.2(3) . . ? C7 C8 H8 120.4 . . ? C9 C8 H8 120.4 . . ? C5 C9 C8 118.5(2) . . ? C5 C9 H9 120.7 . . ? C8 C9 H9 120.7 . . ? N3 C10 C2 110.9(2) . . ? N3 C10 H10A 109.5 . . ? C2 C10 H10A 109.5 . . ? N3 C10 H10B 109.5 . . ? C2 C10 H10B 109.5 . . ? H10A C10 H10B 108.1 . . ? N3 C11 C12 118.4(2) . . ? N3 C11 H11 120.8 . . ? C12 C11 H11 120.8 . . ? N4 C12 C16 122.1(3) . . ? N4 C12 C11 116.2(2) . . ? C16 C12 C11 121.5(3) . . ? N4 C13 C14 122.8(3) . . ? N4 C13 H13 118.6 . . ? C14 C13 H13 118.6 . . ? C15 C14 C13 118.8(3) . . ? C15 C14 H14 120.6 . . ? C13 C14 H14 120.6 . . ? C14 C15 C16 119.1(3) . . ? C14 C15 H15 120.4 . . ? C16 C15 H15 120.4 . . ? C15 C16 C12 119.5(3) . . ? C15 C16 H16 120.3 . . ? C12 C16 H16 120.3 . . ? N5 C17 C2 110.4(2) . . ? N5 C17 H17A 109.6 . . ? C2 C17 H17A 109.6 . . ? N5 C17 H17B 109.6 . . ? C2 C17 H17B 109.6 . . ? H17A C17 H17B 108.1 . . ? N5 C18 C19 118.7(2) . . ? N5 C18 H18 120.7 . . ? C19 C18 H18 120.7 . . ? N6 C19 C23 122.2(2) . . ? N6 C19 C18 115.4(2) . . ? C23 C19 C18 122.4(2) . . ? N6 C20 C21 123.1(3) . . ? N6 C20 H20 118.5 . . ? C21 C20 H20 118.5 . . ? C22 C21 C20 118.7(3) . . ? C22 C21 H21 120.6 . . ? C20 C21 H21 120.6 . . ? C21 C22 C23 119.4(3) . . ? C21 C22 H22 120.3 . . ? C23 C22 H22 120.3 . . ? C22 C23 C19 118.9(3) . . ? C22 C23 H23 120.6 . . ? C19 C23 H23 120.6 . . ? C4 N1 C3 120.1(2) . . ? C4 N1 Zn1 115.13(16) . . ? C3 N1 Zn1 121.95(15) . . ? C6 N2 C5 117.9(2) . . ? C6 N2 Zn1 128.39(17) . . ? C5 N2 Zn1 113.62(16) . . ? C11 N3 C10 121.0(2) . . ? C11 N3 Zn1 115.76(19) . . ? C10 N3 Zn1 122.41(16) . . ? C13 N4 C12 117.8(2) . . ? C13 N4 Zn1 129.23(19) . . ? C12 N4 Zn1 113.01(17) . . ? C18 N5 C17 120.8(2) . . ? C18 N5 Zn1 113.93(17) . . ? C17 N5 Zn1 122.26(16) . . ? C20 N6 C19 117.7(2) . . ? C20 N6 Zn1 128.00(18) . . ? C19 N6 Zn1 114.24(16) . . ? C1 O1 H1O 124.6(14) . . ? O3A Cl1 O4A 125.8(7) . . ? O5 Cl1 O4A 108.5(6) . . ? O3A Cl1 O3 112.1(5) . . ? O5 Cl1 O3 122.5(4) . . ? O3A Cl1 O2 115.5(5) . . ? O5 Cl1 O2 107.8(2) . . ? O4A Cl1 O2 109.3(6) . . ? O3 Cl1 O2 111.3(3) . . ? O3A Cl1 O5A 105.1(7) . . ? O4A Cl1 O5A 85.3(7) . . ? O3 Cl1 O5A 101.0(6) . . ? O2 Cl1 O5A 110.6(6) . . ? O5 Cl1 O4 109.9(4) . . ? O4A Cl1 O4 114.6(5) . . ? O3 Cl1 O4 97.3(4) . . ? O2 Cl1 O4 106.5(2) . . ? O5A Cl1 O4 128.5(6) . . ? O8 Cl2 O7A 110.0(7) . . ? O8 Cl2 O6 103.4(5) . . ? O7A Cl2 O6 107.3(7) . . ? O8 Cl2 O9 113.4(6) . . ? O7A Cl2 O9 105.7(8) . . ? O6 Cl2 O9 116.9(7) . . ? O7 Cl2A O6A 110.7(6) . . ? O7 Cl2A O8 114.8(5) . . ? O6A Cl2A O8 108.8(4) . . ? O7 Cl2A O9A 107.7(6) . . ? O6A Cl2A O9A 107.1(6) . . ? O8 Cl2A O9A 107.4(4) . . ? N3 Zn1 N6 109.81(8) . . ? N3 Zn1 N1 82.11(8) . . ? N6 Zn1 N1 151.32(8) . . ? N3 Zn1 N2 153.66(8) . . ? N6 Zn1 N2 96.33(8) . . ? N1 Zn1 N2 76.11(7) . . ? N3 Zn1 N4 76.42(8) . . ? N6 Zn1 N4 97.30(8) . . ? N1 Zn1 N4 111.03(8) . . ? N2 Zn1 N4 97.64(8) . . ? N3 Zn1 N5 81.00(8) . . ? N6 Zn1 N5 76.03(8) . . ? N1 Zn1 N5 80.47(8) . . ? N2 Zn1 N5 109.35(8) . . ? N4 Zn1 N5 152.68(8) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C17 -68.0(3) . . . . ? O1 C1 C2 C3 172.0(2) . . . . ? O1 C1 C2 C10 52.4(3) . . . . ? C17 C2 C3 N1 45.2(3) . . . . ? C1 C2 C3 N1 162.6(2) . . . . ? C10 C2 C3 N1 -79.8(3) . . . . ? N1 C4 C5 N2 -6.6(3) . . . . ? N1 C4 C5 C9 175.4(3) . . . . ? N2 C6 C7 C8 1.5(4) . . . . ? C6 C7 C8 C9 -2.6(4) . . . . ? N2 C5 C9 C8 1.0(4) . . . . ? C4 C5 C9 C8 178.9(3) . . . . ? C7 C8 C9 C5 1.4(4) . . . . ? C17 C2 C10 N3 -80.0(3) . . . . ? C1 C2 C10 N3 161.5(2) . . . . ? C3 C2 C10 N3 45.4(3) . . . . ? N3 C11 C12 N4 -5.1(4) . . . . ? N3 C11 C12 C16 178.5(3) . . . . ? N4 C13 C14 C15 -0.5(4) . . . . ? C13 C14 C15 C16 0.1(4) . . . . ? C14 C15 C16 C12 0.6(4) . . . . ? N4 C12 C16 C15 -1.0(4) . . . . ? C11 C12 C16 C15 175.3(3) . . . . ? C1 C2 C17 N5 165.1(2) . . . . ? C3 C2 C17 N5 -78.8(2) . . . . ? C10 C2 C17 N5 46.4(3) . . . . ? N5 C18 C19 N6 -11.6(3) . . . . ? N5 C18 C19 C23 167.9(2) . . . . ? N6 C20 C21 C22 1.8(5) . . . . ? C20 C21 C22 C23 -0.1(5) . . . . ? C21 C22 C23 C19 -1.3(4) . . . . ? N6 C19 C23 C22 1.2(4) . . . . ? C18 C19 C23 C22 -178.3(3) . . . . ? C5 C4 N1 C3 174.7(2) . . . . ? C5 C4 N1 Zn1 13.4(3) . . . . ? C2 C3 N1 C4 -128.2(2) . . . . ? C2 C3 N1 Zn1 31.8(3) . . . . ? C7 C6 N2 C5 0.9(4) . . . . ? C7 C6 N2 Zn1 -175.1(2) . . . . ? C9 C5 N2 C6 -2.1(4) . . . . ? C4 C5 N2 C6 179.9(2) . . . . ? C9 C5 N2 Zn1 174.4(2) . . . . ? C4 C5 N2 Zn1 -3.6(3) . . . . ? C12 C11 N3 C10 173.4(2) . . . . ? C12 C11 N3 Zn1 3.3(3) . . . . ? C2 C10 N3 C11 -140.0(3) . . . . ? C2 C10 N3 Zn1 29.5(3) . . . . ? C14 C13 N4 C12 0.2(4) . . . . ? C14 C13 N4 Zn1 -179.65(19) . . . . ? C16 C12 N4 C13 0.6(4) . . . . ? C11 C12 N4 C13 -175.8(2) . . . . ? C16 C12 N4 Zn1 -179.6(2) . . . . ? C11 C12 N4 Zn1 4.0(3) . . . . ? C19 C18 N5 C17 176.0(2) . . . . ? C19 C18 N5 Zn1 15.2(3) . . . . ? C2 C17 N5 C18 -130.4(2) . . . . ? C2 C17 N5 Zn1 28.9(3) . . . . ? C21 C20 N6 C19 -2.0(4) . . . . ? C21 C20 N6 Zn1 176.1(2) . . . . ? C23 C19 N6 C20 0.5(4) . . . . ? C18 C19 N6 C20 179.9(2) . . . . ? C23 C19 N6 Zn1 -177.9(2) . . . . ? C18 C19 N6 Zn1 1.5(3) . . . . ? Cl2A O8 Cl2 O7A -54.3(11) . . . . ? Cl2A O8 Cl2 O6 -168.7(14) . . . . ? Cl2A O8 Cl2 O9 63.7(12) . . . . ? Cl2 O8 Cl2A O7 68.9(12) . . . . ? Cl2 O8 Cl2A O6A -55.8(11) . . . . ? Cl2 O8 Cl2A O9A -171.3(14) . . . . ? C11 N3 Zn1 N6 -93.9(2) . . . . ? C10 N3 Zn1 N6 96.2(2) . . . . ? C11 N3 Zn1 N1 113.1(2) . . . . ? C10 N3 Zn1 N1 -56.9(2) . . . . ? C11 N3 Zn1 N2 78.8(3) . . . . ? C10 N3 Zn1 N2 -91.2(3) . . . . ? C11 N3 Zn1 N4 -0.88(19) . . . . ? C10 N3 Zn1 N4 -170.9(2) . . . . ? C11 N3 Zn1 N5 -165.4(2) . . . . ? C10 N3 Zn1 N5 24.6(2) . . . . ? C20 N6 Zn1 N3 111.3(2) . . . . ? C19 N6 Zn1 N3 -70.53(18) . . . . ? C20 N6 Zn1 N1 -137.9(2) . . . . ? C19 N6 Zn1 N1 40.2(3) . . . . ? C20 N6 Zn1 N2 -65.4(2) . . . . ? C19 N6 Zn1 N2 112.76(17) . . . . ? C20 N6 Zn1 N4 33.1(2) . . . . ? C19 N6 Zn1 N4 -148.68(17) . . . . ? C20 N6 Zn1 N5 -173.8(2) . . . . ? C19 N6 Zn1 N5 4.34(16) . . . . ? C4 N1 Zn1 N3 -176.54(19) . . . . ? C3 N1 Zn1 N3 22.48(19) . . . . ? C4 N1 Zn1 N6 66.1(3) . . . . ? C3 N1 Zn1 N6 -94.9(2) . . . . ? C4 N1 Zn1 N2 -11.47(18) . . . . ? C3 N1 Zn1 N2 -172.4(2) . . . . ? C4 N1 Zn1 N4 -104.43(19) . . . . ? C3 N1 Zn1 N4 94.59(19) . . . . ? C4 N1 Zn1 N5 101.33(19) . . . . ? C3 N1 Zn1 N5 -59.64(19) . . . . ? C6 N2 Zn1 N3 -141.2(2) . . . . ? C5 N2 Zn1 N3 42.7(3) . . . . ? C6 N2 Zn1 N6 31.8(2) . . . . ? C5 N2 Zn1 N6 -144.25(17) . . . . ? C6 N2 Zn1 N1 -176.3(2) . . . . ? C5 N2 Zn1 N1 7.62(17) . . . . ? C6 N2 Zn1 N4 -66.5(2) . . . . ? C5 N2 Zn1 N4 117.48(17) . . . . ? C6 N2 Zn1 N5 109.2(2) . . . . ? C5 N2 Zn1 N5 -66.87(18) . . . . ? C13 N4 Zn1 N3 178.0(2) . . . . ? C12 N4 Zn1 N3 -1.82(17) . . . . ? C13 N4 Zn1 N6 -73.3(2) . . . . ? C12 N4 Zn1 N6 106.88(17) . . . . ? C13 N4 Zn1 N1 102.1(2) . . . . ? C12 N4 Zn1 N1 -77.68(18) . . . . ? C13 N4 Zn1 N2 24.1(2) . . . . ? C12 N4 Zn1 N2 -155.69(17) . . . . ? C13 N4 Zn1 N5 -146.9(2) . . . . ? C12 N4 Zn1 N5 33.3(3) . . . . ? C18 N5 Zn1 N3 102.54(19) . . . . ? C17 N5 Zn1 N3 -58.00(18) . . . . ? C18 N5 Zn1 N6 -10.60(18) . . . . ? C17 N5 Zn1 N6 -171.14(19) . . . . ? C18 N5 Zn1 N1 -174.02(19) . . . . ? C17 N5 Zn1 N1 25.44(18) . . . . ? C18 N5 Zn1 N2 -102.49(19) . . . . ? C17 N5 Zn1 N2 96.96(19) . . . . ? C18 N5 Zn1 N4 68.1(3) . . . . ? C17 N5 Zn1 N4 -92.5(2) . . . . ? 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 O1 H1O O9A 0.861(10) 2.16(2) 2.951(7) 152(4) 1_455 O1 H1O O9 0.861(10) 2.28(2) 3.003(8) 142(3) 1_455 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 28.27 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.951 _refine_diff_density_min -0.474 _refine_diff_density_rms 0.067 data_1_5 _database_code_depnum_ccdc_archive 'CCDC 845935' #TrackingRef 'combined_final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H25 Cd Cl2 N6 O9.50' _chemical_formula_weight 720.79 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' Cd Cd -0.8075 1.2024 '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/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 9.6739(6) _cell_length_b 15.4973(6) _cell_length_c 18.3160(12) _cell_angle_alpha 90.00 _cell_angle_beta 92.495(3) _cell_angle_gamma 90.00 _cell_volume 2743.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 78435 _cell_measurement_theta_min 2.59 _cell_measurement_theta_max 25.68 _exptl_crystal_description parallelepiped _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.745 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1452 _exptl_absorpt_coefficient_mu 1.056 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.552 _exptl_absorpt_correction_T_max 0.872 _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 four \w scans with 2\% steps (392 frames)' _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 78435 _diffrn_reflns_av_R_equivalents 0.0386 _diffrn_reflns_av_sigmaI/netI 0.0431 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.59 _diffrn_reflns_theta_max 25.68 _reflns_number_total 5197 _reflns_number_gt 4286 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 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. One perchlorate ion is disordered over two positions sharing three O atoms, with occupancy parameters which have been refined, then fixed to 0.5. The water solvent molecule O10 has been given a 0.5 occupancy parameter since it is close to one of the disordered perchlorate O atoms. All non-hydrogen atoms were refined with anisotropic displacement parameters, with restraints for some badly behaving perchlorate O atoms. The H atom bound to O1 was found on a Fourier-difference map and the C-bound H atoms were introduced at calculated positions. All were treated as riding atoms with an isotropic displacement parameter equal to 1.2 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^)+(0.0667P)^2^+3.6213P] 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 0.0032(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5197 _refine_ls_number_parameters 398 _refine_ls_number_restraints 36 _refine_ls_R_factor_all 0.0564 _refine_ls_R_factor_gt 0.0445 _refine_ls_wR_factor_ref 0.1231 _refine_ls_wR_factor_gt 0.1169 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.086 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.140 _refine_diff_density_min -0.927 _refine_diff_density_rms 0.105 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 Cd Cd 0.14707(3) 0.841859(19) 0.221492(17) 0.03712(15) Uani 1 1 d . . . Cl1 Cl 0.35123(12) 0.02731(9) 0.64059(8) 0.0600(4) Uani 1 1 d . . . Cl2A Cl 0.3120(3) 0.32314(18) 0.55394(16) 0.0580(6) Uani 0.50 1 d P . . Cl2B Cl 0.2335(3) 0.3579(2) 0.52488(14) 0.0567(6) Uani 0.50 1 d P . . O1 O -0.3435(4) 0.8229(3) 0.0410(2) 0.0758(12) Uani 1 1 d . . . H1 H -0.4330 0.8260 0.0354 0.091 Uiso 1 1 d R . . O2 O 0.3967(3) 0.1025(2) 0.6819(2) 0.0590(9) Uani 1 1 d . . . O3 O 0.4634(4) -0.0157(3) 0.6125(3) 0.0880(15) Uani 1 1 d U . . O4 O 0.2519(7) 0.0474(4) 0.5869(4) 0.149(3) Uani 1 1 d U . . O5 O 0.2871(8) -0.0305(5) 0.6879(4) 0.176(3) Uani 1 1 d U . . O6A O 0.4532(8) 0.2907(6) 0.5695(5) 0.077(2) Uani 0.50 1 d P . . O6B O 0.1177(11) 0.4085(8) 0.4943(6) 0.100(3) Uani 0.50 1 d PU . . O7 O 0.2258(6) 0.2632(3) 0.5154(3) 0.1104(19) Uani 1 1 d U . . O8 O 0.2439(5) 0.3592(3) 0.6115(3) 0.0902(15) Uani 1 1 d . . . O9 O 0.3423(5) 0.3920(3) 0.5002(2) 0.0767(12) Uani 1 1 d . . . O10 O -0.5280(11) 0.9296(6) 0.0345(5) 0.084(3) Uani 0.50 1 d PU . . N1 N 0.0546(4) 0.7539(3) 0.1292(2) 0.0460(9) Uani 1 1 d . . . N2 N -0.0617(3) 0.7967(2) 0.26919(19) 0.0382(8) Uani 1 1 d . . . N3 N -0.0180(4) 0.9334(2) 0.16343(19) 0.0389(8) Uani 1 1 d . . . N4 N 0.3009(4) 0.7281(2) 0.2051(2) 0.0451(9) Uani 1 1 d . . . N5 N 0.1643(4) 0.8555(2) 0.34746(19) 0.0377(8) Uani 1 1 d . . . N6 N 0.2587(4) 0.9642(2) 0.18242(19) 0.0406(8) Uani 1 1 d . . . C1 C -0.0827(5) 0.7684(3) 0.0944(3) 0.0509(12) Uani 1 1 d . . . H1A H -0.1203 0.7137 0.0772 0.061 Uiso 1 1 calc R . . H1B H -0.0737 0.8056 0.0522 0.061 Uiso 1 1 calc R . . C2 C -0.1801(4) 0.7665(3) 0.2228(2) 0.0445(10) Uani 1 1 d . . . H2A H -0.2653 0.7790 0.2468 0.053 Uiso 1 1 calc R . . H2B H -0.1738 0.7045 0.2168 0.053 Uiso 1 1 calc R . . C3 C -0.1630(4) 0.9092(3) 0.1511(3) 0.0465(11) Uani 1 1 d . . . H3A H -0.1984 0.9352 0.1059 0.056 Uiso 1 1 calc R . . H3B H -0.2159 0.9320 0.1906 0.056 Uiso 1 1 calc R . . C4 C -0.1845(4) 0.8102(3) 0.1467(2) 0.0426(10) Uani 1 1 d . . . C5 C -0.3327(5) 0.7959(4) 0.1154(3) 0.0563(13) Uani 1 1 d . . . H5A H -0.3564 0.7352 0.1186 0.068 Uiso 1 1 calc R . . H5B H -0.3972 0.8285 0.1437 0.068 Uiso 1 1 calc R . . C6 C 0.1272(5) 0.6898(3) 0.1123(3) 0.0516(12) Uani 1 1 d . . . H6 H 0.0958 0.6529 0.0751 0.062 Uiso 1 1 calc R . . C7 C 0.2608(5) 0.6729(3) 0.1508(3) 0.0504(12) Uani 1 1 d . . . C8 C 0.3408(7) 0.6007(3) 0.1352(3) 0.0667(17) Uani 1 1 d . . . H8 H 0.3137 0.5640 0.0970 0.080 Uiso 1 1 calc R . . C9 C 0.4607(6) 0.5838(3) 0.1770(4) 0.0678(17) Uani 1 1 d . . . H9 H 0.5139 0.5355 0.1674 0.081 Uiso 1 1 calc R . . C10 C 0.5001(6) 0.6388(3) 0.2323(3) 0.0593(14) Uani 1 1 d . . . H10 H 0.5799 0.6284 0.2610 0.071 Uiso 1 1 calc R . . C11 C 0.4190(5) 0.7102(3) 0.2445(3) 0.0509(12) Uani 1 1 d . . . H11 H 0.4471 0.7480 0.2817 0.061 Uiso 1 1 calc R . . C12 C -0.0763(4) 0.8138(3) 0.3364(2) 0.0374(9) Uani 1 1 d . . . H12 H -0.1618 0.8068 0.3569 0.045 Uiso 1 1 calc R . . C13 C 0.0446(4) 0.8450(3) 0.3816(2) 0.0382(9) Uani 1 1 d . . . C14 C 0.0329(5) 0.8631(3) 0.4548(3) 0.0480(11) Uani 1 1 d . . . H14 H -0.0508 0.8555 0.4770 0.058 Uiso 1 1 calc R . . C15 C 0.1478(5) 0.8926(3) 0.4942(3) 0.0524(12) Uani 1 1 d . . . H15 H 0.1419 0.9058 0.5434 0.063 Uiso 1 1 calc R . . C16 C 0.2709(5) 0.9025(3) 0.4608(3) 0.0488(11) Uani 1 1 d . . . H16 H 0.3497 0.9215 0.4869 0.059 Uiso 1 1 calc R . . C17 C 0.2746(4) 0.8832(3) 0.3870(3) 0.0436(10) Uani 1 1 d . . . H17 H 0.3578 0.8899 0.3640 0.052 Uiso 1 1 calc R . . C18 C 0.0331(5) 0.9928(3) 0.1262(2) 0.0407(9) Uani 1 1 d . . . H18 H -0.0213 1.0215 0.0908 0.049 Uiso 1 1 calc R . . C19 C 0.1806(5) 1.0168(3) 0.1390(2) 0.0415(10) Uani 1 1 d . . . C20 C 0.2343(5) 1.0901(3) 0.1078(3) 0.0506(11) Uani 1 1 d . . . H20 H 0.1790 1.1246 0.0771 0.061 Uiso 1 1 calc R . . C21 C 0.3723(6) 1.1114(4) 0.1231(3) 0.0594(14) Uani 1 1 d . . . H21 H 0.4104 1.1604 0.1026 0.071 Uiso 1 1 calc R . . C22 C 0.4510(6) 1.0595(4) 0.1685(3) 0.0599(14) Uani 1 1 d . . . H22 H 0.5430 1.0729 0.1801 0.072 Uiso 1 1 calc R . . C23 C 0.3908(5) 0.9862(3) 0.1969(3) 0.0491(11) Uani 1 1 d . . . H23 H 0.4449 0.9507 0.2275 0.059 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 Cd 0.0302(2) 0.0394(2) 0.0421(2) -0.00455(13) 0.00632(12) -0.00145(12) Cl1 0.0322(6) 0.0652(8) 0.0822(9) -0.0223(7) -0.0019(5) -0.0013(5) Cl2A 0.0577(16) 0.0576(14) 0.0602(15) -0.0031(12) 0.0198(13) -0.0149(13) Cl2B 0.0439(13) 0.0743(17) 0.0519(14) 0.0128(13) 0.0014(11) -0.0184(13) O1 0.055(2) 0.119(4) 0.052(2) 0.011(2) -0.0101(18) -0.029(2) O2 0.0401(18) 0.058(2) 0.078(2) -0.0195(18) -0.0020(16) 0.0041(15) O3 0.048(2) 0.071(3) 0.144(4) -0.049(3) -0.002(2) 0.0089(19) O4 0.152(5) 0.121(4) 0.166(5) -0.079(4) -0.095(4) 0.079(4) O5 0.182(6) 0.174(6) 0.179(6) -0.050(5) 0.080(5) -0.124(5) O6A 0.056(5) 0.093(6) 0.084(6) 0.002(5) 0.014(4) -0.001(4) O6B 0.077(5) 0.129(7) 0.093(6) 0.016(6) -0.008(5) 0.011(5) O7 0.131(4) 0.107(4) 0.096(3) -0.042(3) 0.051(3) -0.065(3) O8 0.080(3) 0.089(3) 0.105(4) -0.035(3) 0.051(3) -0.025(2) O9 0.098(3) 0.072(3) 0.059(2) 0.012(2) -0.012(2) -0.036(2) O10 0.088(6) 0.089(6) 0.075(5) -0.011(5) -0.007(5) 0.012(5) N1 0.044(2) 0.048(2) 0.047(2) -0.0091(17) 0.0115(17) -0.0130(18) N2 0.0323(17) 0.043(2) 0.0391(19) 0.0012(16) 0.0021(14) -0.0020(15) N3 0.0360(18) 0.0412(19) 0.0397(19) -0.0044(16) 0.0040(15) -0.0001(15) N4 0.038(2) 0.039(2) 0.059(2) 0.0006(18) 0.0163(17) -0.0013(16) N5 0.0338(18) 0.0391(19) 0.0402(19) -0.0018(15) 0.0008(14) 0.0032(14) N6 0.0392(19) 0.042(2) 0.0410(19) -0.0076(16) 0.0089(15) -0.0059(16) C1 0.045(3) 0.064(3) 0.044(3) -0.012(2) 0.004(2) -0.022(2) C2 0.034(2) 0.056(3) 0.043(2) 0.000(2) 0.0018(18) -0.012(2) C3 0.033(2) 0.061(3) 0.046(2) 0.003(2) -0.0001(18) -0.003(2) C4 0.032(2) 0.056(3) 0.040(2) -0.001(2) 0.0012(17) -0.0097(19) C5 0.045(3) 0.079(4) 0.044(3) 0.008(3) -0.006(2) -0.022(3) C6 0.057(3) 0.041(2) 0.057(3) -0.012(2) 0.019(2) -0.017(2) C7 0.050(3) 0.037(2) 0.065(3) -0.001(2) 0.022(2) -0.007(2) C8 0.087(4) 0.031(2) 0.085(4) -0.007(2) 0.041(3) -0.006(3) C9 0.062(3) 0.040(3) 0.105(5) 0.013(3) 0.038(3) 0.013(3) C10 0.052(3) 0.044(3) 0.085(4) 0.018(3) 0.028(3) 0.007(2) C11 0.041(2) 0.046(3) 0.067(3) 0.008(2) 0.019(2) 0.004(2) C12 0.031(2) 0.040(2) 0.042(2) 0.0056(18) 0.0057(17) -0.0002(17) C13 0.036(2) 0.038(2) 0.041(2) 0.0061(18) 0.0017(17) 0.0044(17) C14 0.045(3) 0.057(3) 0.043(3) 0.006(2) 0.005(2) -0.001(2) C15 0.060(3) 0.061(3) 0.036(2) 0.007(2) -0.004(2) -0.003(2) C16 0.048(3) 0.049(3) 0.048(3) 0.010(2) -0.013(2) -0.001(2) C17 0.036(2) 0.042(2) 0.052(3) 0.001(2) -0.0035(19) 0.0024(19) C18 0.044(2) 0.039(2) 0.039(2) -0.0045(19) 0.0026(18) 0.0033(19) C19 0.044(2) 0.041(2) 0.040(2) -0.0086(19) 0.0081(18) -0.0046(19) C20 0.062(3) 0.043(2) 0.047(3) -0.001(2) 0.010(2) -0.007(2) C21 0.063(3) 0.054(3) 0.062(3) -0.010(3) 0.015(3) -0.025(3) C22 0.052(3) 0.063(3) 0.064(3) -0.012(3) 0.006(2) -0.023(3) C23 0.041(2) 0.053(3) 0.054(3) -0.009(2) 0.006(2) -0.012(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 Cd N6 2.311(4) . ? Cd N5 2.316(4) . ? Cd N1 2.321(4) . ? Cd N4 2.334(4) . ? Cd N2 2.342(3) . ? Cd N3 2.355(4) . ? Cl1 O4 1.380(5) . ? Cl1 O3 1.391(4) . ? Cl1 O5 1.409(7) . ? Cl1 O2 1.448(4) . ? Cl2A O8 1.384(5) . ? Cl2A O7 1.415(5) . ? Cl2A O6A 1.471(9) . ? Cl2A O9 1.489(5) . ? Cl2B O9 1.277(5) . ? Cl2B O6B 1.459(11) . ? Cl2B O7 1.479(6) . ? Cl2B O8 1.585(6) . ? O1 C5 1.425(6) . ? O1 H1 0.8683 . ? N1 C6 1.263(6) . ? N1 C1 1.466(6) . ? N2 C12 1.272(5) . ? N2 C2 1.472(5) . ? N3 C18 1.260(6) . ? N3 C3 1.460(5) . ? N4 C11 1.353(6) . ? N4 C7 1.356(6) . ? N5 C17 1.335(6) . ? N5 C13 1.349(6) . ? N6 C23 1.338(6) . ? N6 C19 1.347(6) . ? C1 C4 1.546(6) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C4 1.549(6) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.550(7) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.537(6) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.468(8) . ? C6 H6 0.9300 . ? C7 C8 1.398(7) . ? C8 C9 1.387(9) . ? C8 H8 0.9300 . ? C9 C10 1.364(9) . ? C9 H9 0.9300 . ? C10 C11 1.381(7) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 C13 1.484(6) . ? C12 H12 0.9300 . ? C13 C14 1.379(6) . ? C14 C15 1.377(7) . ? C14 H14 0.9300 . ? C15 C16 1.371(7) . ? C15 H15 0.9300 . ? C16 C17 1.386(7) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 C19 1.483(6) . ? C18 H18 0.9300 . ? C19 C20 1.383(6) . ? C20 C21 1.392(7) . ? C20 H20 0.9300 . ? C21 C22 1.365(8) . ? C21 H21 0.9300 . ? C22 C23 1.387(7) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? 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 N6 Cd N5 102.68(12) . . ? N6 Cd N1 115.26(13) . . ? N5 Cd N1 142.01(13) . . ? N6 Cd N4 105.68(13) . . ? N5 Cd N4 100.26(13) . . ? N1 Cd N4 71.98(14) . . ? N6 Cd N2 141.52(13) . . ? N5 Cd N2 71.41(12) . . ? N1 Cd N2 77.59(12) . . ? N4 Cd N2 112.80(12) . . ? N6 Cd N3 71.51(13) . . ? N5 Cd N3 114.39(12) . . ? N1 Cd N3 78.03(14) . . ? N4 Cd N3 145.13(13) . . ? N2 Cd N3 76.67(12) . . ? O4 Cl1 O3 112.0(4) . . ? O4 Cl1 O5 105.7(5) . . ? O3 Cl1 O5 107.1(4) . . ? O4 Cl1 O2 112.2(3) . . ? O3 Cl1 O2 110.8(2) . . ? O5 Cl1 O2 108.8(3) . . ? O8 Cl2A O7 110.8(3) . . ? O8 Cl2A O6A 117.3(5) . . ? O7 Cl2A O6A 113.2(5) . . ? O8 Cl2A O9 109.1(3) . . ? O7 Cl2A O9 105.6(3) . . ? O6A Cl2A O9 99.5(4) . . ? O9 Cl2B O6B 105.9(5) . . ? O9 Cl2B O7 114.0(4) . . ? O6B Cl2B O7 117.1(6) . . ? O9 Cl2B O8 109.3(3) . . ? O6B Cl2B O8 113.1(5) . . ? O7 Cl2B O8 97.4(3) . . ? C5 O1 H1 99.2 . . ? C6 N1 C1 121.2(4) . . ? C6 N1 Cd 116.1(3) . . ? C1 N1 Cd 122.7(3) . . ? C12 N2 C2 120.5(4) . . ? C12 N2 Cd 115.6(3) . . ? C2 N2 Cd 122.8(3) . . ? C18 N3 C3 120.1(4) . . ? C18 N3 Cd 114.2(3) . . ? C3 N3 Cd 122.9(3) . . ? C11 N4 C7 118.0(4) . . ? C11 N4 Cd 128.0(3) . . ? C7 N4 Cd 114.0(3) . . ? C17 N5 C13 118.0(4) . . ? C17 N5 Cd 126.2(3) . . ? C13 N5 Cd 115.1(3) . . ? C23 N6 C19 118.0(4) . . ? C23 N6 Cd 127.1(3) . . ? C19 N6 Cd 114.9(3) . . ? N1 C1 C4 112.6(4) . . ? N1 C1 H1A 109.1 . . ? C4 C1 H1A 109.1 . . ? N1 C1 H1B 109.1 . . ? C4 C1 H1B 109.1 . . ? H1A C1 H1B 107.8 . . ? N2 C2 C4 111.7(3) . . ? N2 C2 H2A 109.3 . . ? C4 C2 H2A 109.3 . . ? N2 C2 H2B 109.3 . . ? C4 C2 H2B 109.3 . . ? H2A C2 H2B 107.9 . . ? N3 C3 C4 112.9(4) . . ? N3 C3 H3A 109.0 . . ? C4 C3 H3A 109.0 . . ? N3 C3 H3B 109.0 . . ? C4 C3 H3B 109.0 . . ? H3A C3 H3B 107.8 . . ? C5 C4 C2 105.2(3) . . ? C5 C4 C1 108.5(4) . . ? C2 C4 C1 112.5(4) . . ? C5 C4 C3 106.5(4) . . ? C2 C4 C3 112.8(4) . . ? C1 C4 C3 111.1(4) . . ? O1 C5 C4 110.1(4) . . ? O1 C5 H5A 109.6 . . ? C4 C5 H5A 109.6 . . ? O1 C5 H5B 109.6 . . ? C4 C5 H5B 109.6 . . ? H5A C5 H5B 108.2 . . ? N1 C6 C7 120.6(4) . . ? N1 C6 H6 119.7 . . ? C7 C6 H6 119.7 . . ? N4 C7 C8 120.8(5) . . ? N4 C7 C6 117.3(4) . . ? C8 C7 C6 121.8(5) . . ? C9 C8 C7 119.7(6) . . ? C9 C8 H8 120.2 . . ? C7 C8 H8 120.2 . . ? C10 C9 C8 119.5(5) . . ? C10 C9 H9 120.3 . . ? C8 C9 H9 120.3 . . ? C9 C10 C11 118.6(6) . . ? C9 C10 H10 120.7 . . ? C11 C10 H10 120.7 . . ? N4 C11 C10 123.4(5) . . ? N4 C11 H11 118.3 . . ? C10 C11 H11 118.3 . . ? N2 C12 C13 119.3(4) . . ? N2 C12 H12 120.3 . . ? C13 C12 H12 120.3 . . ? N5 C13 C14 122.2(4) . . ? N5 C13 C12 116.9(4) . . ? C14 C13 C12 120.9(4) . . ? C15 C14 C13 118.6(4) . . ? C15 C14 H14 120.7 . . ? C13 C14 H14 120.7 . . ? C16 C15 C14 120.0(5) . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? C15 C16 C17 118.1(4) . . ? C15 C16 H16 121.0 . . ? C17 C16 H16 121.0 . . ? N5 C17 C16 123.0(4) . . ? N5 C17 H17 118.5 . . ? C16 C17 H17 118.5 . . ? N3 C18 C19 119.6(4) . . ? N3 C18 H18 120.2 . . ? C19 C18 H18 120.2 . . ? N6 C19 C20 121.9(4) . . ? N6 C19 C18 117.0(4) . . ? C20 C19 C18 121.1(4) . . ? C19 C20 C21 119.1(5) . . ? C19 C20 H20 120.4 . . ? C21 C20 H20 120.4 . . ? C22 C21 C20 119.1(5) . . ? C22 C21 H21 120.4 . . ? C20 C21 H21 120.4 . . ? C21 C22 C23 118.6(5) . . ? C21 C22 H22 120.7 . . ? C23 C22 H22 120.7 . . ? N6 C23 C22 123.2(5) . . ? N6 C23 H23 118.4 . . ? C22 C23 H23 118.4 . . ? 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 O1 H1 O10 0.87 1.85 2.432(11) 122.7 . data_1_6 _database_code_depnum_ccdc_archive 'CCDC 845936' #TrackingRef 'combined_final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H21 Cl2 Cu N5 O1' _chemical_formula_weight 445.84 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.6820(17) _cell_length_b 13.293(3) _cell_length_c 16.419(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1894.9(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7800 _cell_measurement_theta_min 2.14 _cell_measurement_theta_max 30.35 _exptl_crystal_description irregular _exptl_crystal_colour Green _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.549 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 908 _exptl_absorpt_coefficient_mu 1.447 _exptl_absorpt_correction_type NONE _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details 'crystal-to-detector distance 60 mm' _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.76999 _diffrn_radiation_type 'synchrotron radiation' _diffrn_radiation_source 'synchrotron radiation' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'ADSC Quantum210' _diffrn_measurement_method 'two \f and two \w scans with 2\% steps' _diffrn_detector_area_resol_mean 0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 7800 _diffrn_reflns_av_R_equivalents 0.0596 _diffrn_reflns_av_sigmaI/netI 0.0606 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 30.35 _reflns_number_total 4063 _reflns_number_gt 3699 _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 ; 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^)+(0.1649P)^2^+3.7076P] 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 0.069(8) _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 0.00(1) _refine_ls_number_reflns 4063 _refine_ls_number_parameters 237 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0924 _refine_ls_R_factor_gt 0.0863 _refine_ls_wR_factor_ref 0.2660 _refine_ls_wR_factor_gt 0.2525 _refine_ls_goodness_of_fit_ref 1.148 _refine_ls_restrained_S_all 1.148 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _chemical_absolute_configuration unk 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 Cu1 Cu 0.57304(12) 0.66556(6) 0.18630(5) 0.0379(4) Uani 1 1 d . . . Cl1 Cl 0.4517(3) 0.64304(13) 0.32250(10) 0.0420(5) Uani 1 1 d . . . Cl2 Cl 0.6122(3) 0.83213(12) 0.17649(12) 0.0467(5) Uani 1 1 d . . . N1 N 0.7890(8) 0.6295(5) 0.2232(4) 0.0375(14) Uani 1 1 d . . . N2 N 0.5779(8) 0.5197(4) 0.1514(3) 0.0332(13) Uani 1 1 d . . . N3 N 0.3701(9) 0.6590(5) 0.1246(4) 0.0424(15) Uani 1 1 d . . . N4 N 0.7179(9) 0.3633(4) 0.1858(4) 0.0397(14) Uani 1 1 d . . . H4B H 0.7975 0.3424 0.2165 0.048 Uiso 1 1 d R . . N5 N 0.4008(10) 0.3851(5) 0.1101(4) 0.0418(16) Uani 1 1 d . . . H5A H 0.3009 0.3748 0.0980 0.050 Uiso 1 1 d R . . O1 O 0.8598(11) 0.4663(6) -0.0474(5) 0.072(2) Uani 1 1 d . . . H1 H 0.9254 0.4397 -0.0761 0.109 Uiso 1 1 calc R . . C1 C 0.9034(12) 0.6920(6) 0.2432(5) 0.047(2) Uani 1 1 d . . . H1A H 0.8861 0.7608 0.2386 0.057 Uiso 1 1 calc R . . C2 C 1.0457(12) 0.6601(6) 0.2703(5) 0.050(2) Uani 1 1 d . . . H2 H 1.1235 0.7054 0.2835 0.060 Uiso 1 1 calc R . . C3 C 1.0668(12) 0.5568(7) 0.2768(5) 0.0485(19) Uani 1 1 d . . . H3 H 1.1603 0.5323 0.2960 0.058 Uiso 1 1 calc R . . C4 C 0.9545(13) 0.4907(6) 0.2559(5) 0.047(2) Uani 1 1 d . . . H4 H 0.9700 0.4216 0.2596 0.056 Uiso 1 1 calc R . . C5 C 0.8168(11) 0.5298(5) 0.2293(4) 0.0383(16) Uani 1 1 d . . . C6 C 0.6782(10) 0.4620(5) 0.2106(4) 0.0355(16) Uani 1 1 d . . . H6 H 0.6194 0.4555 0.2613 0.043 Uiso 1 1 calc R . . C7 C 0.7609(11) 0.3515(6) 0.0997(5) 0.0444(18) Uani 1 1 d . . . H7A H 0.7591 0.2805 0.0861 0.053 Uiso 1 1 calc R . . H7B H 0.8658 0.3751 0.0926 0.053 Uiso 1 1 calc R . . C8 C 0.6565(12) 0.4079(6) 0.0399(5) 0.0434(19) Uani 1 1 d . . . C9 C 0.7268(12) 0.4044(7) -0.0447(5) 0.049(2) Uani 1 1 d . . . H9A H 0.7545 0.3357 -0.0581 0.059 Uiso 1 1 calc R . . H9B H 0.6522 0.4276 -0.0844 0.059 Uiso 1 1 calc R . . C10 C 0.4905(11) 0.3678(6) 0.0360(4) 0.0436(19) Uani 1 1 d . . . H10A H 0.4381 0.3995 -0.0094 0.052 Uiso 1 1 calc R . . H10B H 0.4939 0.2960 0.0253 0.052 Uiso 1 1 calc R . . C11 C 0.4131(11) 0.4811(5) 0.1476(4) 0.0375(16) Uani 1 1 d . . . H11 H 0.3775 0.4735 0.2039 0.045 Uiso 1 1 calc R . . C12 C 0.6488(11) 0.5163(5) 0.0683(4) 0.0382(17) Uani 1 1 d . . . H12A H 0.7516 0.5448 0.0699 0.046 Uiso 1 1 calc R . . H12B H 0.5873 0.5555 0.0305 0.046 Uiso 1 1 calc R . . C13 C 0.3174(10) 0.5647(5) 0.1093(4) 0.0342(15) Uani 1 1 d . . . C14 C 0.1894(13) 0.5457(7) 0.0666(5) 0.052(2) Uani 1 1 d . . . H14 H 0.1581 0.4799 0.0568 0.062 Uiso 1 1 calc R . . C15 C 0.1045(11) 0.6266(7) 0.0372(5) 0.050(2) Uani 1 1 d . . . H15 H 0.0173 0.6156 0.0055 0.061 Uiso 1 1 calc R . . C16 C 0.1504(14) 0.7225(7) 0.0553(6) 0.058(2) Uani 1 1 d . . . H16 H 0.0913 0.7772 0.0386 0.070 Uiso 1 1 calc R . . C17 C 0.2850(13) 0.7375(7) 0.0983(5) 0.052(2) Uani 1 1 d . . . H17 H 0.3175 0.8027 0.1095 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 Cu1 0.0538(7) 0.0245(5) 0.0353(5) -0.0016(3) -0.0001(4) 0.0007(4) Cl1 0.0589(12) 0.0321(8) 0.0350(8) 0.0028(6) -0.0009(8) 0.0038(7) Cl2 0.0720(14) 0.0247(8) 0.0435(9) 0.0005(6) 0.0016(8) -0.0009(8) N1 0.041(4) 0.029(3) 0.043(3) -0.002(2) 0.004(3) -0.003(3) N2 0.043(4) 0.023(2) 0.033(3) -0.0034(19) 0.000(3) -0.003(2) N3 0.059(5) 0.029(3) 0.039(3) 0.000(2) 0.003(3) 0.002(3) N4 0.057(4) 0.025(3) 0.037(3) 0.003(2) -0.007(3) 0.002(3) N5 0.053(5) 0.032(3) 0.040(3) -0.001(2) 0.000(3) -0.011(3) O1 0.093(6) 0.064(4) 0.060(4) -0.029(3) 0.035(4) -0.026(4) C1 0.056(6) 0.036(4) 0.050(4) -0.006(3) 0.010(4) -0.017(4) C2 0.063(6) 0.038(4) 0.049(4) -0.014(3) -0.002(4) -0.007(4) C3 0.044(5) 0.054(5) 0.047(4) -0.005(3) -0.002(4) 0.011(4) C4 0.072(6) 0.029(3) 0.039(3) -0.005(3) 0.000(4) 0.004(4) C5 0.052(5) 0.027(3) 0.036(3) -0.004(3) 0.002(3) 0.004(3) C6 0.049(5) 0.023(3) 0.035(3) -0.001(2) -0.002(3) -0.001(3) C7 0.057(5) 0.031(4) 0.044(4) -0.004(3) 0.003(3) 0.007(3) C8 0.065(6) 0.029(3) 0.036(3) -0.005(3) 0.005(4) -0.004(3) C9 0.061(6) 0.044(4) 0.042(4) -0.013(3) 0.011(4) -0.006(4) C10 0.065(6) 0.031(3) 0.036(3) -0.008(3) -0.001(3) -0.002(3) C11 0.050(5) 0.031(3) 0.031(3) -0.001(2) -0.002(3) -0.008(3) C12 0.057(5) 0.021(3) 0.036(3) 0.000(2) 0.001(3) 0.003(3) C13 0.038(4) 0.030(3) 0.035(3) 0.003(2) 0.004(3) 0.000(3) C14 0.076(7) 0.046(4) 0.034(3) 0.006(3) -0.006(4) -0.005(4) C15 0.042(5) 0.063(5) 0.047(4) 0.010(4) -0.017(4) -0.007(4) C16 0.073(7) 0.051(5) 0.051(5) 0.013(4) -0.004(5) 0.007(5) C17 0.076(7) 0.039(4) 0.042(4) 0.008(3) -0.003(4) -0.001(4) _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 Cu1 N2 2.022(5) . ? Cu1 N1 2.028(7) . ? Cu1 N3 2.035(8) . ? Cu1 Cl2 2.2460(19) . ? Cu1 Cl1 2.490(2) . ? N1 C1 1.335(10) . ? N1 C5 1.351(10) . ? N2 C12 1.499(9) . ? N2 C6 1.513(10) . ? N2 C11 1.521(11) . ? N3 C17 1.349(11) . ? N3 C13 1.358(9) . ? N4 C6 1.417(9) . ? N4 C7 1.470(10) . ? N5 C11 1.421(9) . ? N5 C10 1.463(10) . ? O1 C9 1.419(12) . ? C1 C2 1.380(15) . ? C2 C3 1.390(13) . ? C3 C4 1.356(13) . ? C4 C5 1.375(13) . ? C5 C6 1.534(11) . ? C7 C8 1.532(12) . ? C8 C12 1.515(10) . ? C8 C9 1.517(11) . ? C8 C10 1.538(13) . ? C11 C13 1.523(11) . ? C13 C14 1.338(13) . ? C14 C15 1.391(13) . ? C15 C16 1.369(14) . ? C16 C17 1.381(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 N2 Cu1 N1 80.7(3) . . ? N2 Cu1 N3 80.6(3) . . ? N1 Cu1 N3 160.0(2) . . ? N2 Cu1 Cl2 157.20(18) . . ? N1 Cu1 Cl2 96.56(19) . . ? N3 Cu1 Cl2 97.89(19) . . ? N2 Cu1 Cl1 98.50(18) . . ? N1 Cu1 Cl1 95.41(19) . . ? N3 Cu1 Cl1 94.4(2) . . ? Cl2 Cu1 Cl1 104.30(7) . . ? C1 N1 C5 117.4(8) . . ? C1 N1 Cu1 127.9(6) . . ? C5 N1 Cu1 114.7(6) . . ? C12 N2 C6 109.5(6) . . ? C12 N2 C11 109.8(6) . . ? C6 N2 C11 113.4(5) . . ? C12 N2 Cu1 107.2(4) . . ? C6 N2 Cu1 108.4(4) . . ? C11 N2 Cu1 108.4(5) . . ? C17 N3 C13 118.1(8) . . ? C17 N3 Cu1 126.9(6) . . ? C13 N3 Cu1 115.0(5) . . ? C6 N4 C7 115.9(6) . . ? C11 N5 C10 117.5(6) . . ? N1 C1 C2 123.6(8) . . ? C1 C2 C3 116.5(9) . . ? C4 C3 C2 121.8(9) . . ? C3 C4 C5 117.4(7) . . ? N1 C5 C4 123.3(8) . . ? N1 C5 C6 115.0(7) . . ? C4 C5 C6 121.6(7) . . ? N4 C6 N2 115.2(6) . . ? N4 C6 C5 114.2(7) . . ? N2 C6 C5 106.4(6) . . ? N4 C7 C8 114.4(7) . . ? C12 C8 C9 109.2(6) . . ? C12 C8 C7 107.1(7) . . ? C9 C8 C7 109.5(8) . . ? C12 C8 C10 107.5(7) . . ? C9 C8 C10 109.1(7) . . ? C7 C8 C10 114.3(7) . . ? O1 C9 C8 109.7(7) . . ? N5 C10 C8 114.2(6) . . ? N5 C11 N2 113.0(7) . . ? N5 C11 C13 115.8(6) . . ? N2 C11 C13 106.5(6) . . ? N2 C12 C8 109.1(6) . . ? C14 C13 N3 123.5(8) . . ? C14 C13 C11 122.1(7) . . ? N3 C13 C11 114.4(7) . . ? C13 C14 C15 118.4(8) . . ? C16 C15 C14 119.4(9) . . ? C15 C16 C17 119.5(9) . . ? N3 C17 C16 121.1(9) . . ? _diffrn_measured_fraction_theta_max 0.950 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 1.459 _refine_diff_density_min -2.133 _refine_diff_density_rms 0.176