# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Hongwei Hou' _publ_contact_author_email houhongw@zzu.edu.cn _publ_author_name 'Hongwei Hou' data_complex_1 _database_code_depnum_ccdc_archive 'CCDC 808517' #TrackingRef '- Revised cif-data.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H25 Cd N6 O6' _chemical_formula_weight 569.87 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' O O 0.0106 0.0060 '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' 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 19.772(4) _cell_length_b 9.997(2) _cell_length_c 23.510(5) _cell_angle_alpha 90.00 _cell_angle_beta 105.50(3) _cell_angle_gamma 90.00 _cell_volume 4478.0(16) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6679 _cell_measurement_theta_min 1.7977 _cell_measurement_theta_max 27.8844 _exptl_crystal_description block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.691 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2312 _exptl_absorpt_coefficient_mu 1.027 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7761 _exptl_absorpt_correction_T_max 0.8209 _exptl_absorpt_process_details 'CrystalClear (Rigaku/MSC Inc., 2006)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Rigaku Saturn' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20554 _diffrn_reflns_av_R_equivalents 0.0238 _diffrn_reflns_av_sigmaI/netI 0.0211 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 27.92 _reflns_number_total 5337 _reflns_number_gt 4771 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku/MSC Inc., 2006)' _computing_cell_refinement 'CrystalClear (Rigaku/MSC Inc., 2006)' _computing_data_reduction 'CrystalClear (Rigaku/MSC Inc., 2006)' _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)' _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^)+(0.0520P)^2^+12.0885P] 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 5337 _refine_ls_number_parameters 311 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0458 _refine_ls_R_factor_gt 0.0402 _refine_ls_wR_factor_ref 0.1150 _refine_ls_wR_factor_gt 0.1111 _refine_ls_goodness_of_fit_ref 1.171 _refine_ls_restrained_S_all 1.171 _refine_ls_shift/su_max 0.003 _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 Cd1 Cd 0.367872(11) 0.50424(2) 0.251094(10) 0.02418(9) Uani 1 1 d . . . N1 N 0.26381(15) 0.5273(3) 0.17995(13) 0.0326(6) Uani 1 1 d . . . N2 N 0.17871(17) 0.6285(4) 0.11067(15) 0.0499(9) Uani 1 1 d . . . N3 N 0.15208(15) 0.5281(3) 0.13692(12) 0.0321(6) Uani 1 1 d . . . N4 N 0.30389(17) 0.5195(3) 0.32189(14) 0.0349(6) Uani 1 1 d . . . N5 N 0.23995(17) 0.6381(3) 0.36932(14) 0.0430(7) Uani 1 1 d . . . N6 N 0.27389(17) 0.5361(3) 0.40401(14) 0.0371(7) Uani 1 1 d . . . C1 C 0.2461(2) 0.6226(4) 0.13805(17) 0.0464(10) Uani 1 1 d . . . H1 H 0.2789 0.6798 0.1292 0.056 Uiso 1 1 calc R . . C2 C 0.20256(17) 0.4702(3) 0.17819(14) 0.0302(7) Uani 1 1 d . . . H2 H 0.1961 0.4003 0.2023 0.036 Uiso 1 1 calc R . . C3 C 0.07609(19) 0.5021(4) 0.12365(16) 0.0390(9) Uani 1 1 d . . . H3A H 0.0550 0.5692 0.1433 0.047 Uiso 1 1 calc R . . H3B H 0.0689 0.4156 0.1398 0.047 Uiso 1 1 calc R . . C4 C 0.0860(2) 0.2705(5) 0.0517(2) 0.0572(12) Uani 1 1 d . . . H4A H 0.1178 0.2967 0.0885 0.086 Uiso 1 1 calc R . . H4B H 0.1122 0.2406 0.0251 0.086 Uiso 1 1 calc R . . H4C H 0.0566 0.1992 0.0585 0.086 Uiso 1 1 calc R . . C5 C 0.04079(17) 0.3891(4) 0.02496(16) 0.0357(8) Uani 1 1 d . . . C6 C 0.03875(17) 0.5035(3) 0.05824(15) 0.0324(7) Uani 1 1 d . . . C7 C -0.00106(18) 0.6153(4) 0.03439(15) 0.0352(7) Uani 1 1 d . . . C8 C -0.0013(3) 0.7391(5) 0.0711(2) 0.0577(12) Uani 1 1 d . . . H8A H -0.0402 0.7353 0.0883 0.086 Uiso 1 1 calc R . . H8B H -0.0056 0.8169 0.0465 0.086 Uiso 1 1 calc R . . H8C H 0.0417 0.7438 0.1019 0.086 Uiso 1 1 calc R . . C9 C 0.25955(19) 0.6236(4) 0.32097(16) 0.0364(7) Uani 1 1 d . . . H9 H 0.2444 0.6798 0.2886 0.044 Uiso 1 1 calc R . . C10 C 0.3112(2) 0.4680(4) 0.37548(17) 0.0388(8) Uani 1 1 d . . . H10 H 0.3389 0.3943 0.3905 0.047 Uiso 1 1 calc R . . C11 C 0.2673(3) 0.5224(4) 0.46485(18) 0.0498(10) Uani 1 1 d . . . H11A H 0.2270 0.5736 0.4686 0.060 Uiso 1 1 calc R . . H11B H 0.3087 0.5600 0.4921 0.060 Uiso 1 1 calc R . . C12 C 0.3899(3) 0.3694(6) 0.5338(2) 0.0685(14) Uani 1 1 d . . . H12A H 0.3992 0.4067 0.5728 0.103 Uiso 1 1 calc R . . H12B H 0.3926 0.4387 0.5062 0.103 Uiso 1 1 calc R . . H12C H 0.4240 0.3016 0.5332 0.103 Uiso 1 1 calc R . . C13 C 0.3173(2) 0.3085(4) 0.51688(16) 0.0411(8) Uani 1 1 d . . . C14 C 0.2589(2) 0.3784(4) 0.48189(15) 0.0373(8) Uani 1 1 d . . . C15 C 0.1923(2) 0.3206(4) 0.46473(15) 0.0389(8) Uani 1 1 d . . . C16 C 0.1306(2) 0.3966(5) 0.4263(2) 0.0597(12) Uani 1 1 d . . . H16A H 0.1052 0.4394 0.4508 0.090 Uiso 1 1 calc R . . H16B H 0.1001 0.3355 0.3999 0.090 Uiso 1 1 calc R . . H16C H 0.1474 0.4630 0.4039 0.090 Uiso 1 1 calc R . . C17 C 0.42161(15) 0.2562(3) 0.23820(14) 0.0254(6) Uani 1 1 d . . . C18 C 0.46328(15) 0.1280(3) 0.24358(13) 0.0215(5) Uani 1 1 d . . . C19 C 0.42765(17) 0.0071(3) 0.23740(14) 0.0229(6) Uani 1 1 d . . . H19 H 0.3789 0.0072 0.2291 0.027 Uiso 1 1 calc R . . C20 C 0.46341(15) -0.1152(3) 0.24345(13) 0.0210(5) Uani 1 1 d . . . C21 C 0.42133(15) -0.2424(3) 0.23730(14) 0.0253(6) Uani 1 1 d . . . O1 O 0.43111(13) 0.3465(2) 0.20416(11) 0.0360(5) Uani 1 1 d . . . O2 O 0.37959(14) 0.2678(2) 0.26926(13) 0.0392(6) Uani 1 1 d . . . O3 O 0.43079(13) -0.3331(2) 0.20361(11) 0.0354(5) Uani 1 1 d . . . O4 O 0.37778(14) -0.2528(3) 0.26702(14) 0.0452(7) Uani 1 1 d . . . O5 O 0.47135(14) 0.5084(2) 0.32911(11) 0.0347(5) Uani 1 1 d . . . H5A H 0.4951 0.4428 0.3218 0.052 Uiso 1 1 d R . . H5B H 0.4937 0.5738 0.3199 0.052 Uiso 1 1 d R . . O6 O 0.3350(4) 0.6607(8) 0.5843(3) 0.167(3) Uani 1 1 d D . . H6A H 0.3729 0.6319 0.6075 0.250 Uiso 1 1 d RD . . H6B H 0.3173 0.7190 0.6024 0.250 Uiso 1 1 d RD . . 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 Cd1 0.02062(13) 0.01612(13) 0.03433(15) 0.00062(8) 0.00477(9) -0.00001(7) N1 0.0252(14) 0.0367(15) 0.0336(14) 0.0047(12) 0.0037(11) -0.0014(12) N2 0.0372(17) 0.066(2) 0.0426(17) 0.0243(17) 0.0041(14) -0.0027(16) N3 0.0269(14) 0.0401(16) 0.0256(13) 0.0027(11) 0.0004(11) -0.0023(12) N4 0.0345(16) 0.0321(15) 0.0401(16) 0.0069(12) 0.0136(13) 0.0032(12) N5 0.0457(18) 0.0385(17) 0.0468(18) 0.0049(14) 0.0160(15) 0.0075(14) N6 0.0445(17) 0.0311(14) 0.0379(15) 0.0047(13) 0.0147(13) -0.0004(13) C1 0.0349(19) 0.055(2) 0.047(2) 0.0222(18) 0.0068(16) -0.0066(17) C2 0.0258(15) 0.0312(16) 0.0294(15) 0.0045(13) 0.0004(12) -0.0030(13) C3 0.0237(16) 0.061(3) 0.0287(16) 0.0020(15) 0.0009(13) -0.0035(15) C4 0.047(2) 0.048(2) 0.064(3) 0.002(2) -0.007(2) 0.016(2) C5 0.0225(15) 0.0390(19) 0.0405(18) 0.0004(15) -0.0005(13) 0.0039(14) C6 0.0216(15) 0.045(2) 0.0261(15) -0.0033(13) -0.0009(12) -0.0020(13) C7 0.0269(16) 0.041(2) 0.0346(17) -0.0084(15) 0.0036(13) 0.0019(14) C8 0.063(3) 0.052(3) 0.052(2) -0.018(2) 0.005(2) 0.007(2) C9 0.0347(18) 0.0343(18) 0.0410(18) 0.0066(15) 0.0113(15) 0.0047(14) C10 0.044(2) 0.0312(17) 0.0418(19) 0.0071(15) 0.0118(16) 0.0060(15) C11 0.077(3) 0.038(2) 0.039(2) -0.0026(16) 0.024(2) -0.002(2) C12 0.052(3) 0.078(4) 0.070(3) 0.012(3) 0.008(2) -0.013(3) C13 0.042(2) 0.048(2) 0.0352(18) -0.0023(16) 0.0128(16) -0.0026(17) C14 0.049(2) 0.0364(19) 0.0300(16) 0.0015(14) 0.0170(15) -0.0002(16) C15 0.0405(19) 0.048(2) 0.0316(17) 0.0045(15) 0.0155(15) 0.0079(16) C16 0.051(3) 0.067(3) 0.062(3) 0.017(2) 0.016(2) 0.016(2) C17 0.0222(14) 0.0115(12) 0.0383(16) -0.0023(11) 0.0005(12) -0.0006(10) C18 0.0228(14) 0.0135(12) 0.0279(14) 0.0015(10) 0.0064(11) 0.0020(10) C19 0.0229(14) 0.0136(13) 0.0313(15) -0.0001(10) 0.0059(11) -0.0007(10) C20 0.0236(14) 0.0132(12) 0.0270(13) -0.0011(10) 0.0080(11) -0.0014(10) C21 0.0223(14) 0.0150(13) 0.0368(16) 0.0019(11) 0.0050(12) 0.0006(11) O1 0.0323(12) 0.0187(11) 0.0539(15) 0.0093(10) 0.0061(11) 0.0034(9) O2 0.0401(14) 0.0239(12) 0.0583(15) -0.0013(11) 0.0211(12) 0.0065(10) O3 0.0332(12) 0.0195(11) 0.0526(14) -0.0121(10) 0.0101(11) -0.0019(9) O4 0.0477(16) 0.0280(13) 0.0719(18) -0.0088(13) 0.0369(14) -0.0134(11) O5 0.0293(12) 0.0345(14) 0.0390(13) 0.0011(10) 0.0068(10) -0.0005(9) O6 0.175(6) 0.204(8) 0.113(5) -0.036(5) 0.025(4) 0.042(6) _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 Cd1 N1 2.290(3) . ? Cd1 N4 2.349(3) . ? Cd1 O5 2.355(3) . ? Cd1 O2 2.402(3) . ? Cd1 O1 2.450(3) . ? Cd1 O4 2.457(3) 1_565 ? Cd1 O3 2.486(3) 1_565 ? N1 C2 1.329(4) . ? N1 C1 1.348(5) . ? N2 C1 1.317(5) . ? N2 N3 1.356(4) . ? N3 C2 1.324(4) . ? N3 C3 1.474(4) . ? N4 C10 1.333(5) . ? N4 C9 1.357(4) . ? N5 C9 1.303(5) . ? N5 N6 1.365(4) . ? N6 C10 1.312(5) . ? N6 C11 1.477(5) . ? C1 H1 0.9300 . ? C2 H2 0.9300 . ? C3 C6 1.518(5) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.516(5) . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 C6 1.393(5) . ? C5 C7 1.407(5) 5_565 ? C6 C7 1.395(5) . ? C7 C5 1.407(5) 5_565 ? C7 C8 1.510(5) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C14 1.516(5) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.511(6) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C15 1.391(6) 7_556 ? C13 C14 1.411(5) . ? C14 C15 1.395(5) . ? C15 C13 1.391(6) 7_556 ? C15 C16 1.513(5) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 O2 1.249(4) . ? C17 O1 1.253(4) . ? C17 C18 1.511(4) . ? C18 C19 1.387(4) . ? C18 C18 1.402(6) 2_655 ? C19 C20 1.400(4) . ? C19 H19 0.9300 . ? C20 C20 1.396(6) 2_655 ? C20 C21 1.506(4) . ? C21 O3 1.250(4) . ? C21 O4 1.250(4) . ? O3 Cd1 2.486(3) 1_545 ? O4 Cd1 2.457(3) 1_545 ? O5 H5A 0.8501 . ? O5 H5B 0.8499 . ? O6 H6A 0.8500 . ? O6 H6B 0.8499 . ? 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 Cd1 N4 87.83(11) . . ? N1 Cd1 O5 172.32(10) . . ? N4 Cd1 O5 88.13(10) . . ? N1 Cd1 O2 104.71(10) . . ? N4 Cd1 O2 89.00(9) . . ? O5 Cd1 O2 81.75(9) . . ? N1 Cd1 O1 101.70(10) . . ? N4 Cd1 O1 142.85(9) . . ? O5 Cd1 O1 85.44(9) . . ? O2 Cd1 O1 53.86(8) . . ? N1 Cd1 O4 91.81(11) . 1_565 ? N4 Cd1 O4 82.18(9) . 1_565 ? O5 Cd1 O4 81.17(10) . 1_565 ? O2 Cd1 O4 161.00(12) . 1_565 ? O1 Cd1 O4 132.46(8) . 1_565 ? N1 Cd1 O3 93.79(10) . 1_565 ? N4 Cd1 O3 134.78(9) . 1_565 ? O5 Cd1 O3 84.45(9) . 1_565 ? O2 Cd1 O3 133.43(8) . 1_565 ? O1 Cd1 O3 80.90(8) . 1_565 ? O4 Cd1 O3 52.61(8) 1_565 1_565 ? C2 N1 C1 102.9(3) . . ? C2 N1 Cd1 127.8(2) . . ? C1 N1 Cd1 127.8(2) . . ? C1 N2 N3 102.1(3) . . ? C2 N3 N2 110.4(3) . . ? C2 N3 C3 127.2(3) . . ? N2 N3 C3 122.1(3) . . ? C10 N4 C9 102.6(3) . . ? C10 N4 Cd1 134.6(3) . . ? C9 N4 Cd1 120.4(2) . . ? C9 N5 N6 103.0(3) . . ? C10 N6 N5 109.6(3) . . ? C10 N6 C11 130.9(3) . . ? N5 N6 C11 119.4(3) . . ? N2 C1 N1 114.9(3) . . ? N2 C1 H1 122.6 . . ? N1 C1 H1 122.6 . . ? N3 C2 N1 109.7(3) . . ? N3 C2 H2 125.1 . . ? N1 C2 H2 125.1 . . ? N3 C3 C6 113.9(3) . . ? N3 C3 H3A 108.8 . . ? C6 C3 H3A 108.8 . . ? N3 C3 H3B 108.8 . . ? C6 C3 H3B 108.8 . . ? H3A C3 H3B 107.7 . . ? C5 C4 H4A 109.5 . . ? C5 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C5 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C6 C5 C7 119.4(3) . 5_565 ? C6 C5 C4 120.8(3) . . ? C7 C5 C4 119.9(3) 5_565 . ? C5 C6 C7 122.0(3) . . ? C5 C6 C3 118.8(3) . . ? C7 C6 C3 119.0(3) . . ? C6 C7 C5 118.6(3) . 5_565 ? C6 C7 C8 121.0(3) . . ? C5 C7 C8 120.4(3) 5_565 . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N5 C9 N4 114.4(3) . . ? N5 C9 H9 122.8 . . ? N4 C9 H9 122.8 . . ? N6 C10 N4 110.4(3) . . ? N6 C10 H10 124.8 . . ? N4 C10 H10 124.8 . . ? N6 C11 C14 112.8(3) . . ? N6 C11 H11A 109.0 . . ? C14 C11 H11A 109.0 . . ? N6 C11 H11B 109.0 . . ? C14 C11 H11B 109.0 . . ? H11A C11 H11B 107.8 . . ? C13 C12 H12A 109.5 . . ? C13 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C13 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C15 C13 C14 118.8(4) 7_556 . ? C15 C13 C12 119.4(4) 7_556 . ? C14 C13 C12 121.8(4) . . ? C15 C14 C13 121.8(3) . . ? C15 C14 C11 118.6(4) . . ? C13 C14 C11 119.5(4) . . ? C13 C15 C14 119.4(3) 7_556 . ? C13 C15 C16 119.8(4) 7_556 . ? C14 C15 C16 120.8(4) . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O2 C17 O1 122.9(3) . . ? O2 C17 C18 117.5(3) . . ? O1 C17 C18 119.5(3) . . ? C19 C18 C18 119.37(17) . 2_655 ? C19 C18 C17 118.7(3) . . ? C18 C18 C17 121.88(15) 2_655 . ? C18 C19 C20 121.4(3) . . ? C18 C19 H19 119.3 . . ? C20 C19 H19 119.3 . . ? C20 C20 C19 119.20(17) 2_655 . ? C20 C20 C21 122.32(15) 2_655 . ? C19 C20 C21 118.5(3) . . ? O3 C21 O4 122.4(3) . . ? O3 C21 C20 120.1(3) . . ? O4 C21 C20 117.5(3) . . ? C17 O1 Cd1 89.7(2) . . ? C17 O2 Cd1 91.99(19) . . ? C21 O3 Cd1 90.70(19) . 1_545 ? C21 O4 Cd1 92.1(2) . 1_545 ? Cd1 O5 H5A 103.9 . . ? Cd1 O5 H5B 102.6 . . ? H5A O5 H5B 100.9 . . ? H6A O6 H6B 108.9 . . ? 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 N4 Cd1 N1 C2 -42.1(3) . . . . ? O5 Cd1 N1 C2 -100.4(7) . . . . ? O2 Cd1 N1 C2 46.3(3) . . . . ? O1 Cd1 N1 C2 101.6(3) . . . . ? O4 Cd1 N1 C2 -124.2(3) 1_565 . . . ? O3 Cd1 N1 C2 -176.9(3) 1_565 . . . ? N4 Cd1 N1 C1 121.3(3) . . . . ? O5 Cd1 N1 C1 63.1(8) . . . . ? O2 Cd1 N1 C1 -150.3(3) . . . . ? O1 Cd1 N1 C1 -94.9(3) . . . . ? O4 Cd1 N1 C1 39.2(3) 1_565 . . . ? O3 Cd1 N1 C1 -13.4(3) 1_565 . . . ? C1 N2 N3 C2 1.2(4) . . . . ? C1 N2 N3 C3 175.2(4) . . . . ? N1 Cd1 N4 C10 148.2(4) . . . . ? O5 Cd1 N4 C10 -38.3(4) . . . . ? O2 Cd1 N4 C10 43.5(4) . . . . ? O1 Cd1 N4 C10 41.6(4) . . . . ? O4 Cd1 N4 C10 -119.6(4) 1_565 . . . ? O3 Cd1 N4 C10 -118.6(3) 1_565 . . . ? N1 Cd1 N4 C9 -52.9(3) . . . . ? O5 Cd1 N4 C9 120.6(3) . . . . ? O2 Cd1 N4 C9 -157.6(3) . . . . ? O1 Cd1 N4 C9 -159.5(2) . . . . ? O4 Cd1 N4 C9 39.2(3) 1_565 . . . ? O3 Cd1 N4 C9 40.3(3) 1_565 . . . ? C9 N5 N6 C10 0.2(4) . . . . ? C9 N5 N6 C11 177.2(4) . . . . ? N3 N2 C1 N1 -0.7(5) . . . . ? C2 N1 C1 N2 -0.1(5) . . . . ? Cd1 N1 C1 N2 -166.7(3) . . . . ? N2 N3 C2 N1 -1.3(4) . . . . ? C3 N3 C2 N1 -175.0(3) . . . . ? C1 N1 C2 N3 0.8(4) . . . . ? Cd1 N1 C2 N3 167.5(2) . . . . ? C2 N3 C3 C6 -141.3(4) . . . . ? N2 N3 C3 C6 45.7(5) . . . . ? C7 C5 C6 C7 -0.7(6) 5_565 . . . ? C4 C5 C6 C7 178.5(4) . . . . ? C7 C5 C6 C3 174.1(3) 5_565 . . . ? C4 C5 C6 C3 -6.7(5) . . . . ? N3 C3 C6 C5 81.9(4) . . . . ? N3 C3 C6 C7 -103.1(4) . . . . ? C5 C6 C7 C5 0.7(6) . . . 5_565 ? C3 C6 C7 C5 -174.1(3) . . . 5_565 ? C5 C6 C7 C8 -178.9(4) . . . . ? C3 C6 C7 C8 6.4(5) . . . . ? N6 N5 C9 N4 -0.1(4) . . . . ? C10 N4 C9 N5 0.0(4) . . . . ? Cd1 N4 C9 N5 -164.8(3) . . . . ? N5 N6 C10 N4 -0.3(5) . . . . ? C11 N6 C10 N4 -176.8(4) . . . . ? C9 N4 C10 N6 0.2(4) . . . . ? Cd1 N4 C10 N6 161.6(3) . . . . ? C10 N6 C11 C14 -44.7(6) . . . . ? N5 N6 C11 C14 139.0(4) . . . . ? C15 C13 C14 C15 -0.9(6) 7_556 . . . ? C12 C13 C14 C15 178.0(4) . . . . ? C15 C13 C14 C11 176.0(3) 7_556 . . . ? C12 C13 C14 C11 -5.2(6) . . . . ? N6 C11 C14 C15 -82.4(5) . . . . ? N6 C11 C14 C13 100.6(4) . . . . ? C13 C14 C15 C13 0.9(6) . . . 7_556 ? C11 C14 C15 C13 -176.0(3) . . . 7_556 ? C13 C14 C15 C16 -178.9(4) . . . . ? C11 C14 C15 C16 4.2(5) . . . . ? O2 C17 C18 C19 52.0(4) . . . . ? O1 C17 C18 C19 -129.2(3) . . . . ? O2 C17 C18 C18 -126.0(4) . . . 2_655 ? O1 C17 C18 C18 52.8(5) . . . 2_655 ? C18 C18 C19 C20 -0.3(5) 2_655 . . . ? C17 C18 C19 C20 -178.3(3) . . . . ? C18 C19 C20 C20 0.6(5) . . . 2_655 ? C18 C19 C20 C21 178.8(3) . . . . ? C20 C20 C21 O3 -52.1(5) 2_655 . . . ? C19 C20 C21 O3 129.8(3) . . . . ? C20 C20 C21 O4 127.6(4) 2_655 . . . ? C19 C20 C21 O4 -50.5(4) . . . . ? O2 C17 O1 Cd1 12.9(3) . . . . ? C18 C17 O1 Cd1 -165.9(2) . . . . ? N1 Cd1 O1 C17 -106.69(19) . . . . ? N4 Cd1 O1 C17 -4.6(3) . . . . ? O5 Cd1 O1 C17 76.20(18) . . . . ? O2 Cd1 O1 C17 -6.91(17) . . . . ? O4 Cd1 O1 C17 149.84(18) 1_565 . . . ? O3 Cd1 O1 C17 161.30(19) 1_565 . . . ? O1 C17 O2 Cd1 -13.1(3) . . . . ? C18 C17 O2 Cd1 165.6(2) . . . . ? N1 Cd1 O2 C17 100.8(2) . . . . ? N4 Cd1 O2 C17 -171.7(2) . . . . ? O5 Cd1 O2 C17 -83.4(2) . . . . ? O1 Cd1 O2 C17 6.94(18) . . . . ? O4 Cd1 O2 C17 -109.6(3) 1_565 . . . ? O3 Cd1 O2 C17 -9.2(3) 1_565 . . . ? O4 C21 O3 Cd1 -15.3(3) . . . 1_545 ? C20 C21 O3 Cd1 164.4(2) . . . 1_545 ? O3 C21 O4 Cd1 15.5(3) . . . 1_545 ? C20 C21 O4 Cd1 -164.2(2) . . . 1_545 ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.92 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.549 _refine_diff_density_min -0.824 _refine_diff_density_rms 0.144 #===end data_complex_2 _database_code_depnum_ccdc_archive 'CCDC 808518' #TrackingRef '- Revised cif-data.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H38 Cd N9 O8' _chemical_formula_weight 801.12 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' Cd Cd -0.8075 1.2024 '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 10.233(2) _cell_length_b 14.009(3) _cell_length_c 14.022(3) _cell_angle_alpha 67.35(3) _cell_angle_beta 84.67(3) _cell_angle_gamma 71.07(3) _cell_volume 1753.6(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5636 _cell_measurement_theta_min 2.1052 _cell_measurement_theta_max 27.8884 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.517 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 822 _exptl_absorpt_coefficient_mu 0.687 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8205 _exptl_absorpt_correction_T_max 0.8749 _exptl_absorpt_process_details 'CrystalClear (Rigaku/MSC Inc., 2006)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Rigaku Saturn' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21679 _diffrn_reflns_av_R_equivalents 0.0271 _diffrn_reflns_av_sigmaI/netI 0.0373 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 27.89 _reflns_number_total 8285 _reflns_number_gt 7409 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku/MSC Inc., 2006)' _computing_cell_refinement 'CrystalClear (Rigaku/MSC Inc., 2006)' _computing_data_reduction 'CrystalClear (Rigaku/MSC Inc., 2006)' _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)' _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^)+(0.0652P)^2^+1.0811P] 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 8285 _refine_ls_number_parameters 457 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0574 _refine_ls_R_factor_gt 0.0508 _refine_ls_wR_factor_ref 0.1357 _refine_ls_wR_factor_gt 0.1305 _refine_ls_goodness_of_fit_ref 1.113 _refine_ls_restrained_S_all 1.113 _refine_ls_shift/su_max 0.003 _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 Cd1 Cd 0.79878(2) 0.81564(2) 0.573728(18) 0.04001(10) Uani 1 1 d . . . N1 N 0.8322(4) 0.7129(3) 0.4674(3) 0.0547(8) Uani 1 1 d . . . N2 N 0.7910(3) 0.6067(3) 0.4026(3) 0.0545(8) Uani 1 1 d . . . N3 N 0.8598(4) 0.6662(3) 0.3290(3) 0.0648(10) Uani 1 1 d . . . N4 N 0.7697(4) 0.9201(3) 0.6757(3) 0.0591(9) Uani 1 1 d . . . N5 N 0.7732(4) 1.0548(3) 0.7238(3) 0.0585(9) Uani 1 1 d . . . N6 N 0.8396(3) 0.9557(3) 0.7964(2) 0.0541(8) Uani 1 1 d . . . N7 N 0.6769(3) 1.0729(3) 1.2672(2) 0.0495(7) Uani 1 1 d . . . N8 N 0.8112(4) 1.0705(3) 1.2680(2) 0.0559(8) Uani 1 1 d . . . N9 N 0.7568(3) 0.9659(3) 1.4233(2) 0.0458(7) Uani 1 1 d . . . C1 C 0.7324(4) 1.0276(4) 0.6528(3) 0.0534(9) Uani 1 1 d . . . H1 H 0.6824 1.0789 0.5927 0.064 Uiso 1 1 calc R . . C2 C 0.8376(5) 0.8778(4) 0.7667(3) 0.0676(12) Uani 1 1 d . . . H2 H 0.8779 0.8037 0.8040 0.081 Uiso 1 1 calc R . . C3 C 0.9076(4) 0.9449(4) 0.8886(3) 0.0641(12) Uani 1 1 d . . . H3A H 0.9835 0.9750 0.8679 0.077 Uiso 1 1 calc R . . H3B H 0.9463 0.8682 0.9310 0.077 Uiso 1 1 calc R . . C4 C 0.8111(4) 1.0019(3) 0.9531(3) 0.0495(9) Uani 1 1 d . . . C5 C 0.7289(4) 0.9469(3) 1.0246(3) 0.0494(9) Uani 1 1 d . . . C6 C 0.7237(6) 0.8377(4) 1.0317(4) 0.0760(14) Uani 1 1 d . . . H6A H 0.7393 0.8326 0.9650 0.114 Uiso 1 1 calc R . . H6B H 0.6346 0.8307 1.0541 0.114 Uiso 1 1 calc R . . H6C H 0.7939 0.7804 1.0804 0.114 Uiso 1 1 calc R . . C7 C 0.6514(4) 0.9940(3) 1.0918(3) 0.0478(8) Uani 1 1 d . . . C8 C 0.5617(5) 0.9347(4) 1.1695(3) 0.0686(12) Uani 1 1 d . . . H8A H 0.6188 0.8770 1.2269 0.103 Uiso 1 1 calc R . . H8B H 0.5162 0.9047 1.1366 0.103 Uiso 1 1 calc R . . H8C H 0.4938 0.9851 1.1938 0.103 Uiso 1 1 calc R . . C9 C 0.6582(4) 1.0922(3) 1.0882(3) 0.0469(8) Uani 1 1 d . . . C10 C 0.7343(5) 1.1510(3) 1.0130(3) 0.0536(9) Uani 1 1 d . . . C11 C 0.7375(7) 1.2608(4) 1.0076(4) 0.0857(16) Uani 1 1 d . . . H11A H 0.6461 1.3123 0.9915 0.129 Uiso 1 1 calc R . . H11B H 0.7986 1.2864 0.9549 0.129 Uiso 1 1 calc R . . H11C H 0.7698 1.2531 1.0732 0.129 Uiso 1 1 calc R . . C12 C 0.8120(4) 1.1041(3) 0.9443(3) 0.0496(9) Uani 1 1 d . . . C13 C 0.8965(5) 1.1634(5) 0.8636(3) 0.0759(14) Uani 1 1 d . . . H13A H 0.8572 1.2403 0.8471 0.114 Uiso 1 1 calc R . . H13B H 0.8962 1.1483 0.8024 0.114 Uiso 1 1 calc R . . H13C H 0.9898 1.1392 0.8899 0.114 Uiso 1 1 calc R . . C14 C 0.5907(5) 1.1349(4) 1.1719(3) 0.0579(10) Uani 1 1 d . . . H14A H 0.5812 1.2116 1.1495 0.069 Uiso 1 1 calc R . . H14B H 0.4992 1.1269 1.1842 0.069 Uiso 1 1 calc R . . C15 C 0.6476(4) 1.0096(3) 1.3597(3) 0.0500(9) Uani 1 1 d . . . H15 H 0.5626 0.9979 1.3770 0.060 Uiso 1 1 calc R . . C16 C 0.8530(4) 1.0065(3) 1.3632(3) 0.0524(9) Uani 1 1 d . . . H16 H 0.9420 0.9899 1.3881 0.063 Uiso 1 1 calc R . . C17 C 0.7772(5) 0.6350(4) 0.4840(4) 0.0640(12) Uani 1 1 d . . . H17 H 0.7346 0.6042 0.5444 0.077 Uiso 1 1 calc R . . C18 C 0.8807(4) 0.7285(4) 0.3726(4) 0.0602(11) Uani 1 1 d . . . H18 H 0.9260 0.7798 0.3397 0.072 Uiso 1 1 calc R . . C19 C 0.7449(5) 0.5252(4) 0.3852(4) 0.0685(13) Uani 1 1 d . . . H19A H 0.8184 0.4560 0.4065 0.082 Uiso 1 1 calc R . . H19B H 0.7242 0.5484 0.3121 0.082 Uiso 1 1 calc R . . C20 C 0.6181(4) 0.5113(3) 0.4456(4) 0.0537(10) Uani 1 1 d . . . C21 C 0.6301(4) 0.4292(3) 0.5429(4) 0.0569(10) Uani 1 1 d . . . C22 C 0.7727(5) 0.3538(5) 0.5911(5) 0.0903(17) Uani 1 1 d . . . H22A H 0.7828 0.3559 0.6576 0.136 Uiso 1 1 calc R . . H22B H 0.8428 0.3774 0.5469 0.136 Uiso 1 1 calc R . . H22C H 0.7820 0.2806 0.5990 0.136 Uiso 1 1 calc R . . C23 C 0.4868(5) 0.5827(3) 0.4020(3) 0.0579(10) Uani 1 1 d . . . C24 C 0.4742(7) 0.6725(5) 0.2959(5) 0.0947(18) Uani 1 1 d . . . H24A H 0.4445 0.6519 0.2457 0.142 Uiso 1 1 calc R . . H24B H 0.5624 0.6837 0.2778 0.142 Uiso 1 1 calc R . . H24C H 0.4078 0.7387 0.2969 0.142 Uiso 1 1 calc R . . C25 C 0.5462(4) 0.7573(3) 0.6170(3) 0.0478(8) Uani 1 1 d . . . C26 C 0.4466(3) 0.6962(3) 0.6753(3) 0.0410(7) Uani 1 1 d . . . C27 C 0.4830(4) 0.6102(3) 0.7703(3) 0.0455(8) Uani 1 1 d . . . C28 C 0.6268(5) 0.5637(4) 0.8150(4) 0.0646(11) Uani 1 1 d . . . C29 C 0.3851(4) 0.5643(3) 0.8265(3) 0.0516(9) Uani 1 1 d . . . H29 H 0.4099 0.5071 0.8904 0.062 Uiso 1 1 calc R . . C30 C 0.2494(4) 0.6037(3) 0.7874(3) 0.0516(9) Uani 1 1 d . . . H30 H 0.1829 0.5744 0.8259 0.062 Uiso 1 1 calc R . . C31 C 0.2143(3) 0.6865(3) 0.6911(3) 0.0443(8) Uani 1 1 d . . . C32 C 0.0690(4) 0.7293(3) 0.6455(3) 0.0510(9) Uani 1 1 d . . . C33 C 0.3125(4) 0.7324(3) 0.6363(3) 0.0435(8) Uani 1 1 d . . . H33 H 0.2879 0.7886 0.5718 0.052 Uiso 1 1 calc R . . O1 O 0.6530(3) 0.7346(3) 0.6681(2) 0.0711(9) Uani 1 1 d . . . O2 O 0.5187(3) 0.8244(3) 0.5286(3) 0.0738(9) Uani 1 1 d . . . O3 O 0.7172(4) 0.5057(3) 0.7674(3) 0.0912(11) Uani 1 1 d . . . O4 O 0.65579(16) 0.57430(17) 0.89251(15) 0.1049(14) Uani 1 1 d . . . H4 H 0.7387 0.5441 0.9070 0.126 Uiso 1 1 d R . . O5 O 0.03731(16) 0.81078(17) 0.56402(15) 0.0668(8) Uani 1 1 d R . . O6 O -0.01600(16) 0.68107(17) 0.69253(15) 0.0673(8) Uani 1 1 d R . . O7 O 0.98194(16) 0.43643(17) 0.81668(15) 0.181(3) Uani 1 1 d R . . H7A H 0.9826 0.4995 0.7973 0.218 Uiso 1 1 d R . . H7B H 0.9267 0.4486 0.7714 0.218 Uiso 1 1 d R . . O8 O 0.8993(9) 0.6086(7) 0.9476(10) 0.303(6) Uani 1 1 d . . . H8D H 0.9499 0.5694 0.9193 0.363 Uiso 1 1 d R . . H8E H 0.9296 0.5988 1.0039 0.363 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 Cd1 0.03634(14) 0.05151(17) 0.03925(16) -0.02049(12) 0.00225(10) -0.01894(11) N1 0.0546(19) 0.066(2) 0.065(2) -0.0405(18) 0.0112(16) -0.0301(17) N2 0.0521(18) 0.067(2) 0.068(2) -0.0454(19) 0.0169(16) -0.0284(17) N3 0.064(2) 0.080(3) 0.072(2) -0.046(2) 0.0223(18) -0.034(2) N4 0.077(2) 0.066(2) 0.0411(18) -0.0275(16) 0.0008(16) -0.0220(19) N5 0.070(2) 0.063(2) 0.0440(18) -0.0243(16) -0.0060(16) -0.0169(18) N6 0.0513(18) 0.071(2) 0.0379(16) -0.0285(16) -0.0044(14) -0.0043(16) N7 0.0527(18) 0.0560(19) 0.0378(16) -0.0219(14) 0.0023(13) -0.0094(15) N8 0.061(2) 0.065(2) 0.0411(17) -0.0171(16) 0.0053(15) -0.0228(17) N9 0.0489(17) 0.0558(18) 0.0362(15) -0.0183(13) 0.0016(12) -0.0198(14) C1 0.056(2) 0.063(2) 0.039(2) -0.0199(18) 0.0012(16) -0.0157(19) C2 0.092(3) 0.057(3) 0.043(2) -0.022(2) -0.007(2) -0.005(2) C3 0.050(2) 0.096(3) 0.045(2) -0.040(2) -0.0083(17) -0.003(2) C4 0.0447(19) 0.070(3) 0.0310(17) -0.0249(17) -0.0072(14) -0.0058(18) C5 0.056(2) 0.055(2) 0.0362(18) -0.0182(16) -0.0077(16) -0.0118(18) C6 0.101(4) 0.065(3) 0.064(3) -0.026(2) -0.004(3) -0.025(3) C7 0.0468(19) 0.059(2) 0.0325(17) -0.0150(16) -0.0022(14) -0.0126(17) C8 0.072(3) 0.085(3) 0.051(2) -0.021(2) 0.005(2) -0.035(3) C9 0.050(2) 0.052(2) 0.0312(17) -0.0140(15) -0.0028(14) -0.0073(16) C10 0.069(3) 0.051(2) 0.0380(19) -0.0131(16) -0.0066(17) -0.0174(19) C11 0.127(5) 0.059(3) 0.073(3) -0.022(3) 0.009(3) -0.037(3) C12 0.051(2) 0.069(2) 0.0265(16) -0.0138(16) -0.0041(14) -0.0197(18) C13 0.080(3) 0.115(4) 0.038(2) -0.018(2) 0.002(2) -0.049(3) C14 0.059(2) 0.064(3) 0.040(2) -0.0215(18) -0.0015(17) -0.002(2) C15 0.048(2) 0.061(2) 0.043(2) -0.0240(18) 0.0077(16) -0.0150(18) C16 0.053(2) 0.063(2) 0.046(2) -0.0218(18) 0.0049(17) -0.0243(19) C17 0.071(3) 0.078(3) 0.073(3) -0.048(2) 0.029(2) -0.044(2) C18 0.053(2) 0.074(3) 0.076(3) -0.044(2) 0.019(2) -0.033(2) C19 0.067(3) 0.079(3) 0.095(4) -0.062(3) 0.020(2) -0.036(2) C20 0.053(2) 0.051(2) 0.076(3) -0.037(2) 0.0035(19) -0.0238(18) C21 0.047(2) 0.055(2) 0.076(3) -0.032(2) -0.007(2) -0.0147(18) C22 0.064(3) 0.086(4) 0.103(4) -0.032(3) -0.026(3) 0.002(3) C23 0.069(3) 0.050(2) 0.064(3) -0.026(2) -0.004(2) -0.022(2) C24 0.114(5) 0.074(4) 0.084(4) -0.012(3) -0.004(3) -0.033(3) C25 0.0342(17) 0.055(2) 0.062(2) -0.0298(19) 0.0108(16) -0.0166(16) C26 0.0321(15) 0.0462(18) 0.051(2) -0.0246(16) 0.0073(14) -0.0140(14) C27 0.0351(16) 0.052(2) 0.053(2) -0.0229(17) 0.0019(15) -0.0145(15) C28 0.049(2) 0.074(3) 0.065(3) -0.018(2) 0.002(2) -0.022(2) C29 0.0436(19) 0.054(2) 0.054(2) -0.0131(18) -0.0006(16) -0.0192(17) C30 0.0380(18) 0.062(2) 0.062(2) -0.025(2) 0.0068(16) -0.0243(17) C31 0.0327(16) 0.052(2) 0.056(2) -0.0287(18) 0.0026(15) -0.0139(15) C32 0.0347(17) 0.064(2) 0.066(3) -0.038(2) 0.0000(17) -0.0136(17) C33 0.0384(17) 0.0483(19) 0.0467(19) -0.0201(16) 0.0026(14) -0.0148(15) O1 0.0590(18) 0.103(3) 0.0657(19) -0.0254(18) 0.0071(15) -0.0524(18) O2 0.0530(17) 0.075(2) 0.072(2) -0.0041(17) 0.0102(15) -0.0224(16) O3 0.058(2) 0.090(3) 0.124(3) -0.052(2) 0.003(2) -0.0064(18) O4 0.061(2) 0.177(4) 0.071(2) -0.042(3) -0.0068(18) -0.033(3) O5 0.0425(15) 0.084(2) 0.069(2) -0.0236(18) -0.0079(14) -0.0174(15) O6 0.0354(14) 0.077(2) 0.093(2) -0.0308(18) -0.0005(14) -0.0222(14) O7 0.072(3) 0.304(9) 0.207(7) -0.174(7) 0.017(4) -0.018(4) O8 0.210(10) 0.231(10) 0.475(19) -0.204(12) -0.069(11) 0.031(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 Cd1 O1 2.200(3) . ? Cd1 N9 2.286(3) 1_554 ? Cd1 N4 2.350(3) . ? Cd1 N1 2.377(3) . ? Cd1 O6 2.402(2) 1_655 ? Cd1 O5 2.4123(17) 1_655 ? Cd1 C32 2.744(4) 1_655 ? N1 C17 1.320(5) . ? N1 C18 1.335(5) . ? N2 C17 1.328(5) . ? N2 N3 1.356(5) . ? N2 C19 1.474(5) . ? N3 C18 1.318(5) . ? N4 C2 1.334(5) . ? N4 C1 1.339(5) . ? N5 C1 1.335(5) . ? N5 N6 1.361(5) . ? N6 C2 1.316(6) . ? N6 C3 1.458(5) . ? N7 C15 1.332(5) . ? N7 N8 1.364(5) . ? N7 C14 1.465(5) . ? N8 C16 1.306(5) . ? N9 C15 1.318(5) . ? N9 C16 1.357(5) . ? N9 Cd1 2.286(3) 1_556 ? C1 H1 0.9300 . ? C2 H2 0.9300 . ? C3 C4 1.520(5) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C12 1.392(6) . ? C4 C5 1.406(6) . ? C5 C7 1.397(5) . ? C5 C6 1.513(6) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 C9 1.382(5) . ? C7 C8 1.527(6) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 C10 1.411(6) . ? C9 C14 1.527(5) . ? C10 C12 1.413(5) . ? C10 C11 1.522(6) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 C13 1.510(6) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 C20 1.507(6) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.390(6) . ? C20 C23 1.411(6) . ? C21 C23 1.384(6) 2_666 ? C21 C22 1.528(6) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 C21 1.384(6) 2_666 ? C23 C24 1.517(7) . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 O2 1.223(5) . ? C25 O1 1.246(5) . ? C25 C26 1.520(5) . ? C26 C33 1.384(5) . ? C26 C27 1.389(5) . ? C27 C29 1.385(5) . ? C27 C28 1.489(6) . ? C28 O4 1.227(5) . ? C28 O3 1.333(6) . ? C29 C30 1.395(5) . ? C29 H29 0.9300 . ? C30 C31 1.383(5) . ? C30 H30 0.9300 . ? C31 C33 1.381(5) . ? C31 C32 1.511(5) . ? C32 O5 1.240(5) . ? C32 O6 1.257(4) . ? C32 Cd1 2.744(4) 1_455 ? C33 H33 0.9300 . ? O4 H4 0.8200 . ? O5 Cd1 2.4123(17) 1_455 ? O6 Cd1 2.402(2) 1_455 ? O7 H7A 0.8200 . ? O7 H7B 0.8199 . ? O8 H8D 0.8200 . ? O8 H8E 0.8199 . ? 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 Cd1 N9 129.00(12) . 1_554 ? O1 Cd1 N4 90.42(13) . . ? N9 Cd1 N4 92.59(12) 1_554 . ? O1 Cd1 N1 91.23(12) . . ? N9 Cd1 N1 86.25(12) 1_554 . ? N4 Cd1 N1 178.34(12) . . ? O1 Cd1 O6 89.53(10) . 1_655 ? N9 Cd1 O6 141.46(9) 1_554 1_655 ? N4 Cd1 O6 87.50(11) . 1_655 ? N1 Cd1 O6 92.68(11) . 1_655 ? O1 Cd1 O5 143.52(10) . 1_655 ? N9 Cd1 O5 87.47(10) 1_554 1_655 ? N4 Cd1 O5 86.38(11) . 1_655 ? N1 Cd1 O5 92.39(10) . 1_655 ? O6 Cd1 O5 54.0 1_655 1_655 ? O1 Cd1 C32 116.67(13) . 1_655 ? N9 Cd1 C32 114.32(13) 1_554 1_655 ? N4 Cd1 C32 85.41(13) . 1_655 ? N1 Cd1 C32 94.00(12) . 1_655 ? O6 Cd1 C32 27.24(10) 1_655 1_655 ? O5 Cd1 C32 26.85(10) 1_655 1_655 ? C17 N1 C18 102.7(3) . . ? C17 N1 Cd1 124.0(3) . . ? C18 N1 Cd1 132.1(3) . . ? C17 N2 N3 109.4(3) . . ? C17 N2 C19 130.0(4) . . ? N3 N2 C19 120.6(3) . . ? C18 N3 N2 102.1(3) . . ? C2 N4 C1 103.1(3) . . ? C2 N4 Cd1 120.5(3) . . ? C1 N4 Cd1 132.8(3) . . ? C1 N5 N6 102.2(3) . . ? C2 N6 N5 110.0(3) . . ? C2 N6 C3 128.0(4) . . ? N5 N6 C3 121.9(4) . . ? C15 N7 N8 109.8(3) . . ? C15 N7 C14 129.8(4) . . ? N8 N7 C14 120.3(3) . . ? C16 N8 N7 102.2(3) . . ? C15 N9 C16 102.9(3) . . ? C15 N9 Cd1 127.5(3) . 1_556 ? C16 N9 Cd1 126.3(3) . 1_556 ? N5 C1 N4 114.3(4) . . ? N5 C1 H1 122.9 . . ? N4 C1 H1 122.9 . . ? N6 C2 N4 110.4(4) . . ? N6 C2 H2 124.8 . . ? N4 C2 H2 124.8 . . ? N6 C3 C4 113.2(3) . . ? N6 C3 H3A 108.9 . . ? C4 C3 H3A 108.9 . . ? N6 C3 H3B 108.9 . . ? C4 C3 H3B 108.9 . . ? H3A C3 H3B 107.7 . . ? C12 C4 C5 121.7(3) . . ? C12 C4 C3 119.4(4) . . ? C5 C4 C3 118.8(4) . . ? C7 C5 C4 118.9(4) . . ? C7 C5 C6 119.3(4) . . ? C4 C5 C6 121.8(4) . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C9 C7 C5 119.9(4) . . ? C9 C7 C8 121.0(4) . . ? C5 C7 C8 119.1(4) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 C9 C10 121.6(3) . . ? C7 C9 C14 119.6(4) . . ? C10 C9 C14 118.7(4) . . ? C9 C10 C12 118.6(4) . . ? C9 C10 C11 121.1(4) . . ? C12 C10 C11 120.2(4) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C4 C12 C10 119.1(4) . . ? C4 C12 C13 120.5(4) . . ? C10 C12 C13 120.5(4) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N7 C14 C9 109.1(3) . . ? N7 C14 H14A 109.9 . . ? C9 C14 H14A 109.9 . . ? N7 C14 H14B 109.9 . . ? C9 C14 H14B 109.9 . . ? H14A C14 H14B 108.3 . . ? N9 C15 N7 110.1(3) . . ? N9 C15 H15 125.0 . . ? N7 C15 H15 125.0 . . ? N8 C16 N9 115.0(4) . . ? N8 C16 H16 122.5 . . ? N9 C16 H16 122.5 . . ? N1 C17 N2 110.6(4) . . ? N1 C17 H17 124.7 . . ? N2 C17 H17 124.7 . . ? N3 C18 N1 115.3(4) . . ? N3 C18 H18 122.3 . . ? N1 C18 H18 122.3 . . ? N2 C19 C20 110.5(3) . . ? N2 C19 H19A 109.6 . . ? C20 C19 H19A 109.6 . . ? N2 C19 H19B 109.6 . . ? C20 C19 H19B 109.6 . . ? H19A C19 H19B 108.1 . . ? C21 C20 C23 120.3(4) . . ? C21 C20 C19 120.6(4) . . ? C23 C20 C19 119.2(4) . . ? C23 C21 C20 120.2(4) 2_666 . ? C23 C21 C22 119.6(5) 2_666 . ? C20 C21 C22 120.2(4) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21 C23 C20 119.5(4) 2_666 . ? C21 C23 C24 120.4(4) 2_666 . ? C20 C23 C24 120.1(5) . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? O2 C25 O1 124.6(4) . . ? O2 C25 C26 121.2(3) . . ? O1 C25 C26 114.1(4) . . ? C33 C26 C27 118.8(3) . . ? C33 C26 C25 119.0(3) . . ? C27 C26 C25 122.0(3) . . ? C29 C27 C26 120.4(3) . . ? C29 C27 C28 117.7(4) . . ? C26 C27 C28 121.9(3) . . ? O4 C28 O3 123.7(4) . . ? O4 C28 C27 121.6(4) . . ? O3 C28 C27 114.6(4) . . ? C27 C29 C30 120.0(4) . . ? C27 C29 H29 120.0 . . ? C30 C29 H29 120.0 . . ? C31 C30 C29 119.6(3) . . ? C31 C30 H30 120.2 . . ? C29 C30 H30 120.2 . . ? C33 C31 C30 119.8(3) . . ? C33 C31 C32 119.3(4) . . ? C30 C31 C32 120.9(3) . . ? O5 C32 O6 122.3(3) . . ? O5 C32 C31 119.3(3) . . ? O6 C32 C31 118.4(4) . . ? O5 C32 Cd1 61.48(17) . 1_455 ? O6 C32 Cd1 61.03(17) . 1_455 ? C31 C32 Cd1 175.3(3) . 1_455 ? C31 C33 C26 121.3(3) . . ? C31 C33 H33 119.4 . . ? C26 C33 H33 119.4 . . ? C25 O1 Cd1 111.6(3) . . ? C28 O4 H4 109.5 . . ? C32 O5 Cd1 91.67(19) . 1_455 ? C32 O6 Cd1 91.7(2) . 1_455 ? H7A O7 H7B 95.3 . . ? H8D O8 H8E 114.2 . . ? 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 Cd1 N1 C17 -4.4(4) . . . . ? N9 Cd1 N1 C17 -133.4(4) 1_554 . . . ? N4 Cd1 N1 C17 -179(100) . . . . ? O6 Cd1 N1 C17 85.2(4) 1_655 . . . ? O5 Cd1 N1 C17 139.3(4) 1_655 . . . ? C32 Cd1 N1 C17 112.4(4) 1_655 . . . ? O1 Cd1 N1 C18 160.6(4) . . . . ? N9 Cd1 N1 C18 31.6(4) 1_554 . . . ? N4 Cd1 N1 C18 -14(4) . . . . ? O6 Cd1 N1 C18 -109.8(4) 1_655 . . . ? O5 Cd1 N1 C18 -55.7(4) 1_655 . . . ? C32 Cd1 N1 C18 -82.5(4) 1_655 . . . ? C17 N2 N3 C18 -0.9(5) . . . . ? C19 N2 N3 C18 179.3(4) . . . . ? O1 Cd1 N4 C2 80.6(4) . . . . ? N9 Cd1 N4 C2 -150.4(4) 1_554 . . . ? N1 Cd1 N4 C2 -105(4) . . . . ? O6 Cd1 N4 C2 -8.9(4) 1_655 . . . ? O5 Cd1 N4 C2 -63.1(4) 1_655 . . . ? C32 Cd1 N4 C2 -36.2(4) 1_655 . . . ? O1 Cd1 N4 C1 -124.8(4) . . . . ? N9 Cd1 N4 C1 4.3(4) 1_554 . . . ? N1 Cd1 N4 C1 49(4) . . . . ? O6 Cd1 N4 C1 145.7(4) 1_655 . . . ? O5 Cd1 N4 C1 91.6(4) 1_655 . . . ? C32 Cd1 N4 C1 118.5(4) 1_655 . . . ? C1 N5 N6 C2 0.9(5) . . . . ? C1 N5 N6 C3 177.5(4) . . . . ? C15 N7 N8 C16 -1.2(4) . . . . ? C14 N7 N8 C16 -178.4(3) . . . . ? N6 N5 C1 N4 -0.6(5) . . . . ? C2 N4 C1 N5 0.2(5) . . . . ? Cd1 N4 C1 N5 -157.6(3) . . . . ? N5 N6 C2 N4 -0.8(6) . . . . ? C3 N6 C2 N4 -177.2(4) . . . . ? C1 N4 C2 N6 0.4(5) . . . . ? Cd1 N4 C2 N6 161.6(3) . . . . ? C2 N6 C3 C4 -126.9(5) . . . . ? N5 N6 C3 C4 57.1(6) . . . . ? N6 C3 C4 C12 -99.7(5) . . . . ? N6 C3 C4 C5 84.0(5) . . . . ? C12 C4 C5 C7 -3.2(5) . . . . ? C3 C4 C5 C7 173.1(3) . . . . ? C12 C4 C5 C6 177.8(4) . . . . ? C3 C4 C5 C6 -6.0(5) . . . . ? C4 C5 C7 C9 -0.9(5) . . . . ? C6 C5 C7 C9 178.2(4) . . . . ? C4 C5 C7 C8 179.9(4) . . . . ? C6 C5 C7 C8 -1.0(6) . . . . ? C5 C7 C9 C10 4.5(6) . . . . ? C8 C7 C9 C10 -176.3(4) . . . . ? C5 C7 C9 C14 -171.0(3) . . . . ? C8 C7 C9 C14 8.2(5) . . . . ? C7 C9 C10 C12 -4.1(6) . . . . ? C14 C9 C10 C12 171.5(3) . . . . ? C7 C9 C10 C11 178.1(4) . . . . ? C14 C9 C10 C11 -6.3(6) . . . . ? C5 C4 C12 C10 3.6(5) . . . . ? C3 C4 C12 C10 -172.6(3) . . . . ? C5 C4 C12 C13 -177.3(4) . . . . ? C3 C4 C12 C13 6.5(5) . . . . ? C9 C10 C12 C4 0.0(5) . . . . ? C11 C10 C12 C4 177.8(4) . . . . ? C9 C10 C12 C13 -179.2(4) . . . . ? C11 C10 C12 C13 -1.3(6) . . . . ? C15 N7 C14 C9 -118.1(4) . . . . ? N8 N7 C14 C9 58.4(5) . . . . ? C7 C9 C14 N7 75.3(5) . . . . ? C10 C9 C14 N7 -100.4(4) . . . . ? C16 N9 C15 N7 -0.2(4) . . . . ? Cd1 N9 C15 N7 -160.7(2) 1_556 . . . ? N8 N7 C15 N9 1.0(4) . . . . ? C14 N7 C15 N9 177.7(3) . . . . ? N7 N8 C16 N9 1.1(5) . . . . ? C15 N9 C16 N8 -0.6(5) . . . . ? Cd1 N9 C16 N8 160.2(3) 1_556 . . . ? C18 N1 C17 N2 -0.7(5) . . . . ? Cd1 N1 C17 N2 168.0(3) . . . . ? N3 N2 C17 N1 1.0(6) . . . . ? C19 N2 C17 N1 -179.2(4) . . . . ? N2 N3 C18 N1 0.5(5) . . . . ? C17 N1 C18 N3 0.1(6) . . . . ? Cd1 N1 C18 N3 -167.2(3) . . . . ? C17 N2 C19 C20 28.6(7) . . . . ? N3 N2 C19 C20 -151.7(4) . . . . ? N2 C19 C20 C21 -94.6(5) . . . . ? N2 C19 C20 C23 85.4(5) . . . . ? C23 C20 C21 C23 -0.3(6) . . . 2_666 ? C19 C20 C21 C23 179.7(4) . . . 2_666 ? C23 C20 C21 C22 -178.5(4) . . . . ? C19 C20 C21 C22 1.5(6) . . . . ? C21 C20 C23 C21 0.3(6) . . . 2_666 ? C19 C20 C23 C21 -179.7(4) . . . 2_666 ? C21 C20 C23 C24 179.7(4) . . . . ? C19 C20 C23 C24 -0.3(6) . . . . ? O2 C25 C26 C33 -13.1(5) . . . . ? O1 C25 C26 C33 165.1(3) . . . . ? O2 C25 C26 C27 171.7(4) . . . . ? O1 C25 C26 C27 -10.1(5) . . . . ? C33 C26 C27 C29 -2.3(5) . . . . ? C25 C26 C27 C29 172.9(3) . . . . ? C33 C26 C27 C28 177.2(4) . . . . ? C25 C26 C27 C28 -7.6(6) . . . . ? C29 C27 C28 O4 -68.7(6) . . . . ? C26 C27 C28 O4 111.8(5) . . . . ? C29 C27 C28 O3 107.7(5) . . . . ? C26 C27 C28 O3 -71.8(5) . . . . ? C26 C27 C29 C30 0.6(6) . . . . ? C28 C27 C29 C30 -179.0(4) . . . . ? C27 C29 C30 C31 1.9(6) . . . . ? C29 C30 C31 C33 -2.5(6) . . . . ? C29 C30 C31 C32 178.7(4) . . . . ? C33 C31 C32 O5 -6.2(5) . . . . ? C30 C31 C32 O5 172.7(3) . . . . ? C33 C31 C32 O6 174.4(3) . . . . ? C30 C31 C32 O6 -6.7(5) . . . . ? C33 C31 C32 Cd1 -104(4) . . . 1_455 ? C30 C31 C32 Cd1 75(4) . . . 1_455 ? C30 C31 C33 C26 0.7(5) . . . . ? C32 C31 C33 C26 179.6(3) . . . . ? C27 C26 C33 C31 1.7(5) . . . . ? C25 C26 C33 C31 -173.6(3) . . . . ? O2 C25 O1 Cd1 -6.8(5) . . . . ? C26 C25 O1 Cd1 175.0(2) . . . . ? N9 Cd1 O1 C25 20.8(4) 1_554 . . . ? N4 Cd1 O1 C25 114.5(3) . . . . ? N1 Cd1 O1 C25 -65.3(3) . . . . ? O6 Cd1 O1 C25 -158.0(3) 1_655 . . . ? O5 Cd1 O1 C25 -161.0(2) 1_655 . . . ? C32 Cd1 O1 C25 -160.4(3) 1_655 . . . ? O6 C32 O5 Cd1 4.7(4) . . . 1_455 ? C31 C32 O5 Cd1 -174.7(3) . . . 1_455 ? O5 C32 O6 Cd1 -4.7(4) . . . 1_455 ? C31 C32 O6 Cd1 174.7(3) . . . 1_455 ? 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 O4 H4 O8 0.82 2.32 2.909(10) 129.3 . O7 H7B O3 0.82 2.03 2.624(4) 129.1 . O7 H7A O6 0.82 2.40 3.197 163.4 1_655 O8 H8D O8 0.82 2.56 2.952(17) 111.1 2_767 O8 H8E O7 0.82 2.56 3.382(12) 177.7 2_767 _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.89 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 1.156 _refine_diff_density_min -0.584 _refine_diff_density_rms 0.079 #===end data_complex_3 _database_code_depnum_ccdc_archive 'CCDC 808519' #TrackingRef '- Revised cif-data.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H28 Co N6 O8' _chemical_formula_weight 599.46 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pnma loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z+1/2' '-x, y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z-1/2' 'x, -y-1/2, z' _cell_length_a 16.654(3) _cell_length_b 14.174(3) _cell_length_c 11.524(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2720.3(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7244 _cell_measurement_theta_min 2.1490 _cell_measurement_theta_max 27.8485 _exptl_crystal_description block _exptl_crystal_colour purple _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.464 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1244 _exptl_absorpt_coefficient_mu 0.690 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8743 _exptl_absorpt_correction_T_max 0.8859 _exptl_absorpt_process_details 'CrystalClear (Rigaku/MSC Inc., 2006)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Rigaku Saturn' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16981 _diffrn_reflns_av_R_equivalents 0.0419 _diffrn_reflns_av_sigmaI/netI 0.0311 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2789 _reflns_number_gt 2680 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku/MSC Inc., 2006)' _computing_cell_refinement 'CrystalClear (Rigaku/MSC Inc., 2006)' _computing_data_reduction 'CrystalClear (Rigaku/MSC Inc., 2006)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0387P)^2^+1.9392P] 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 2789 _refine_ls_number_parameters 210 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0575 _refine_ls_R_factor_gt 0.0545 _refine_ls_wR_factor_ref 0.1136 _refine_ls_wR_factor_gt 0.1120 _refine_ls_goodness_of_fit_ref 1.218 _refine_ls_restrained_S_all 1.218 _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 Co1 Co 0.03022(3) 0.7500 0.48926(4) 0.03031(17) Uani 1 2 d S . . O1 O 0.09274(16) 0.7500 0.3463(2) 0.0484(8) Uani 1 2 d S . . O2 O 0.21976(17) 0.7500 0.4011(2) 0.0578(9) Uani 1 2 d S . . O3 O 0.01322(16) 0.7500 -0.0467(2) 0.0496(8) Uani 1 2 d S . . H3 H -0.0188 0.7304 -0.0950 0.060 Uiso 0.50 1 d PR . . O4 O 0.09891(18) 0.7500 -0.1947(2) 0.0586(9) Uani 1 2 d S . . O5 O 0.42801(14) 0.7500 0.0994(2) 0.0360(6) Uani 1 2 d S . . O6 O 0.40009(17) 0.7500 -0.0850(2) 0.0574(9) Uani 1 2 d S . . N1 N 0.05592(13) 0.62705(17) 0.56996(19) 0.0378(6) Uani 1 1 d . . . N2 N 0.05227(15) 0.50260(17) 0.6804(2) 0.0422(6) Uani 1 1 d . . . N3 N 0.10972(19) 0.4848(2) 0.6002(3) 0.0684(9) Uani 1 1 d . . . C1 C 0.1099(2) 0.5615(3) 0.5357(3) 0.0565(9) Uani 1 1 d . . . H1 H 0.1439 0.5697 0.4725 0.068 Uiso 1 1 calc R . . C2 C 0.02113(18) 0.5868(2) 0.6609(2) 0.0434(7) Uani 1 1 d . . . H2 H -0.0196 0.6141 0.7048 0.052 Uiso 1 1 calc R . . C3 C 0.0282(2) 0.4307(2) 0.7666(3) 0.0534(9) Uani 1 1 d . . . H3A H 0.0700 0.3831 0.7713 0.064 Uiso 1 1 calc R . . H3B H -0.0204 0.4000 0.7399 0.064 Uiso 1 1 calc R . . C4 C 0.0136(2) 0.4710(2) 0.8872(2) 0.0430(7) Uani 1 1 d . . . C5 C -0.06469(19) 0.4939(2) 0.9213(3) 0.0445(7) Uani 1 1 d . . . C6 C -0.1351(2) 0.4926(3) 0.8381(3) 0.0615(9) Uani 1 1 d . . . H6A H -0.1753 0.4497 0.8662 0.092 Uiso 1 1 calc R . . H6B H -0.1172 0.4725 0.7629 0.092 Uiso 1 1 calc R . . H6C H -0.1576 0.5548 0.8325 0.092 Uiso 1 1 calc R . . C7 C 0.07808(19) 0.4785(2) 0.9634(3) 0.0459(7) Uani 1 1 d . . . C8 C 0.1630(2) 0.4578(3) 0.9234(4) 0.0751(12) Uani 1 1 d . . . H8A H 0.1665 0.4659 0.8408 0.113 Uiso 1 1 calc R . . H8B H 0.1768 0.3940 0.9432 0.113 Uiso 1 1 calc R . . H8C H 0.1996 0.5004 0.9609 0.113 Uiso 1 1 calc R . . C9 C 0.1674(2) 0.7500 0.3268(3) 0.0315(8) Uani 1 2 d S . . C10 C 0.1895(2) 0.7500 0.2001(3) 0.0279(8) Uani 1 2 d S . . C11 C 0.1303(2) 0.7500 0.1155(3) 0.0298(8) Uani 1 2 d S . . H11 H 0.0766 0.7500 0.1375 0.036 Uiso 1 2 calc SR . . C12 C 0.1500(2) 0.7500 -0.0014(3) 0.0300(8) Uani 1 2 d S . . C13 C 0.0855(2) 0.7500 -0.0914(3) 0.0372(9) Uani 1 2 d S . . C14 C 0.2303(2) 0.7500 -0.0338(3) 0.0345(9) Uani 1 2 d S . . H14 H 0.2440 0.7500 -0.1120 0.041 Uiso 1 2 calc SR . . C15 C 0.2899(2) 0.7500 0.0497(3) 0.0309(8) Uani 1 2 d S . . C16 C 0.3774(2) 0.7500 0.0178(3) 0.0351(9) Uani 1 2 d S . . C17 C 0.2695(2) 0.7500 0.1672(3) 0.0300(8) Uani 1 2 d S . . H17 H 0.3096 0.7500 0.2233 0.036 Uiso 1 2 calc SR . . O7 O 0.10838(17) 0.2500 0.1853(2) 0.0606(10) Uani 1 2 d S . . H1A H 0.1095 0.2500 0.2590 0.073 Uiso 1 2 d SR . . H2A H 0.1578 0.2500 0.1670 0.073 Uiso 1 2 d SR . . O8 O 0.2663(2) 0.2500 0.1366(3) 0.1094(19) Uani 1 2 d S . . H3C H 0.2797 0.2500 0.0654 0.131 Uiso 1 2 d SR . . H4 H 0.2979 0.2500 0.1946 0.131 Uiso 1 2 d SR . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.0221(3) 0.0480(3) 0.0208(3) 0.000 0.0005(2) 0.000 O1 0.0273(14) 0.089(2) 0.0288(14) 0.000 0.0074(12) 0.000 O2 0.0341(16) 0.116(3) 0.0238(14) 0.000 -0.0014(13) 0.000 O3 0.0258(14) 0.089(3) 0.0336(15) 0.000 -0.0066(12) 0.000 O4 0.0372(16) 0.117(3) 0.0222(15) 0.000 -0.0056(13) 0.000 O5 0.0230(12) 0.0560(17) 0.0290(14) 0.000 0.0015(11) 0.000 O6 0.0303(15) 0.119(3) 0.0229(14) 0.000 0.0057(12) 0.000 N1 0.0357(12) 0.0491(15) 0.0287(12) 0.0003(11) 0.0008(10) 0.0019(11) N2 0.0567(15) 0.0391(14) 0.0309(12) -0.0010(11) 0.0046(12) 0.0023(12) N3 0.081(2) 0.0604(19) 0.0640(19) 0.0081(16) 0.0301(17) 0.0156(17) C1 0.057(2) 0.059(2) 0.053(2) 0.0078(17) 0.0253(17) 0.0089(17) C2 0.0463(17) 0.0514(18) 0.0327(15) 0.0010(14) 0.0074(13) 0.0039(15) C3 0.088(3) 0.0368(17) 0.0354(16) 0.0003(13) 0.0104(17) -0.0025(17) C4 0.066(2) 0.0318(15) 0.0313(15) 0.0035(12) 0.0060(15) 0.0011(14) C5 0.0619(19) 0.0344(16) 0.0373(16) 0.0066(13) -0.0017(15) -0.0015(15) C6 0.071(2) 0.057(2) 0.057(2) 0.0017(18) -0.0127(19) -0.0041(19) C7 0.0572(19) 0.0385(16) 0.0418(17) 0.0054(13) 0.0077(15) 0.0066(15) C8 0.069(2) 0.089(3) 0.068(3) 0.002(2) 0.009(2) 0.023(2) C9 0.0281(19) 0.043(2) 0.0236(18) 0.000 0.0006(16) 0.000 C10 0.0252(18) 0.034(2) 0.0247(18) 0.000 0.0020(15) 0.000 C11 0.0215(17) 0.039(2) 0.0292(19) 0.000 -0.0002(15) 0.000 C12 0.0230(18) 0.042(2) 0.0249(18) 0.000 -0.0014(15) 0.000 C13 0.031(2) 0.051(2) 0.030(2) 0.000 -0.0060(17) 0.000 C14 0.029(2) 0.053(2) 0.0216(18) 0.000 0.0011(15) 0.000 C15 0.0229(18) 0.043(2) 0.0269(18) 0.000 0.0023(15) 0.000 C16 0.0256(19) 0.054(3) 0.0261(19) 0.000 0.0016(16) 0.000 C17 0.0245(18) 0.042(2) 0.0236(18) 0.000 -0.0017(15) 0.000 O7 0.0290(15) 0.124(3) 0.0289(15) 0.000 -0.0029(13) 0.000 O8 0.0359(19) 0.260(6) 0.0319(18) 0.000 0.0049(16) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 O1 1.948(3) . ? Co1 O5 1.985(2) 6_556 ? Co1 N1 2.021(2) 8_575 ? Co1 N1 2.021(2) . ? O1 C9 1.263(4) . ? O2 C9 1.223(4) . ? O3 C13 1.310(5) . ? O3 H3 0.8200 . ? O4 C13 1.211(5) . ? O5 C16 1.263(4) . ? O5 Co1 1.985(2) 6_656 ? O6 C16 1.243(4) . ? N1 C2 1.326(4) . ? N1 C1 1.352(4) . ? N2 C2 1.320(4) . ? N2 N3 1.354(4) . ? N2 C3 1.478(4) . ? N3 C1 1.316(4) . ? C1 H1 0.9300 . ? C2 H2 0.9300 . ? C3 C4 1.522(4) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C7 1.391(4) . ? C4 C5 1.400(4) . ? C5 C7 1.403(4) 5_567 ? C5 C6 1.516(4) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 C5 1.403(4) 5_567 ? C7 C8 1.516(5) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 C10 1.506(5) . ? C10 C17 1.385(5) . ? C10 C11 1.386(5) . ? C11 C12 1.386(5) . ? C11 H11 0.9300 . ? C12 C14 1.388(5) . ? C12 C13 1.493(5) . ? C14 C15 1.382(5) . ? C14 H14 0.9300 . ? C15 C17 1.395(5) . ? C15 C16 1.503(5) . ? C17 H17 0.9300 . ? O7 H1A 0.8500 . ? O7 H2A 0.8500 . ? O8 H3C 0.8501 . ? O8 H4 0.8499 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Co1 O5 91.34(11) . 6_556 ? O1 Co1 N1 106.01(7) . 8_575 ? O5 Co1 N1 114.73(7) 6_556 8_575 ? O1 Co1 N1 106.01(7) . . ? O5 Co1 N1 114.73(7) 6_556 . ? N1 Co1 N1 119.14(13) 8_575 . ? C9 O1 Co1 132.6(3) . . ? C13 O3 H3 109.3 . . ? C16 O5 Co1 100.9(2) . 6_656 ? C2 N1 C1 103.0(3) . . ? C2 N1 Co1 129.9(2) . . ? C1 N1 Co1 126.8(2) . . ? C2 N2 N3 109.2(3) . . ? C2 N2 C3 129.2(3) . . ? N3 N2 C3 121.4(3) . . ? C1 N3 N2 103.5(3) . . ? N3 C1 N1 113.6(3) . . ? N3 C1 H1 123.2 . . ? N1 C1 H1 123.2 . . ? N2 C2 N1 110.6(3) . . ? N2 C2 H2 124.7 . . ? N1 C2 H2 124.7 . . ? N2 C3 C4 113.4(2) . . ? N2 C3 H3A 108.9 . . ? C4 C3 H3A 108.9 . . ? N2 C3 H3B 108.9 . . ? C4 C3 H3B 108.9 . . ? H3A C3 H3B 107.7 . . ? C7 C4 C5 121.6(3) . . ? C7 C4 C3 118.8(3) . . ? C5 C4 C3 119.5(3) . . ? C4 C5 C7 118.6(3) . 5_567 ? C4 C5 C6 122.7(3) . . ? C7 C5 C6 118.7(3) 5_567 . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C4 C7 C5 119.8(3) . 5_567 ? C4 C7 C8 120.9(3) . . ? C5 C7 C8 119.3(3) 5_567 . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O2 C9 O1 125.3(3) . . ? O2 C9 C10 120.3(3) . . ? O1 C9 C10 114.5(3) . . ? C17 C10 C11 119.4(3) . . ? C17 C10 C9 120.1(3) . . ? C11 C10 C9 120.5(3) . . ? C10 C11 C12 121.0(3) . . ? C10 C11 H11 119.5 . . ? C12 C11 H11 119.5 . . ? C11 C12 C14 119.3(3) . . ? C11 C12 C13 120.3(3) . . ? C14 C12 C13 120.4(3) . . ? O4 C13 O3 123.8(4) . . ? O4 C13 C12 123.4(4) . . ? O3 C13 C12 112.8(3) . . ? C15 C14 C12 120.2(3) . . ? C15 C14 H14 119.9 . . ? C12 C14 H14 119.9 . . ? C14 C15 C17 120.1(3) . . ? C14 C15 C16 121.7(3) . . ? C17 C15 C16 118.2(3) . . ? O6 C16 O5 120.4(3) . . ? O6 C16 C15 121.9(3) . . ? O5 C16 C15 117.7(3) . . ? C10 C17 C15 119.9(3) . . ? C10 C17 H17 120.0 . . ? C15 C17 H17 120.0 . . ? H1A O7 H2A 103.0 . . ? H3C O8 H4 126.6 . . ? 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 O5 Co1 O1 C9 180.0 6_556 . . . ? N1 Co1 O1 C9 63.77(7) 8_575 . . . ? N1 Co1 O1 C9 -63.77(7) . . . . ? O1 Co1 N1 C2 -169.3(3) . . . . ? O5 Co1 N1 C2 -70.1(3) 6_556 . . . ? N1 Co1 N1 C2 71.5(3) 8_575 . . . ? O1 Co1 N1 C1 4.3(3) . . . . ? O5 Co1 N1 C1 103.4(3) 6_556 . . . ? N1 Co1 N1 C1 -114.9(3) 8_575 . . . ? C2 N2 N3 C1 0.2(4) . . . . ? C3 N2 N3 C1 175.6(3) . . . . ? N2 N3 C1 N1 0.0(4) . . . . ? C2 N1 C1 N3 -0.1(4) . . . . ? Co1 N1 C1 N3 -175.1(2) . . . . ? N3 N2 C2 N1 -0.3(4) . . . . ? C3 N2 C2 N1 -175.3(3) . . . . ? C1 N1 C2 N2 0.2(3) . . . . ? Co1 N1 C2 N2 174.94(19) . . . . ? C2 N2 C3 C4 -45.7(5) . . . . ? N3 N2 C3 C4 139.9(3) . . . . ? N2 C3 C4 C7 -88.0(4) . . . . ? N2 C3 C4 C5 96.2(4) . . . . ? C7 C4 C5 C7 -2.3(5) . . . 5_567 ? C3 C4 C5 C7 173.4(3) . . . 5_567 ? C7 C4 C5 C6 175.9(3) . . . . ? C3 C4 C5 C6 -8.4(4) . . . . ? C5 C4 C7 C5 2.3(5) . . . 5_567 ? C3 C4 C7 C5 -173.4(3) . . . 5_567 ? C5 C4 C7 C8 -177.2(3) . . . . ? C3 C4 C7 C8 7.1(4) . . . . ? Co1 O1 C9 O2 0.0 . . . . ? Co1 O1 C9 C10 180.0 . . . . ? O2 C9 C10 C17 0.0 . . . . ? O1 C9 C10 C17 180.0 . . . . ? O2 C9 C10 C11 180.0 . . . . ? O1 C9 C10 C11 0.0 . . . . ? C17 C10 C11 C12 0.0 . . . . ? C9 C10 C11 C12 180.0 . . . . ? C10 C11 C12 C14 0.0 . . . . ? C10 C11 C12 C13 180.0 . . . . ? C11 C12 C13 O4 180.0 . . . . ? C14 C12 C13 O4 0.0 . . . . ? C11 C12 C13 O3 0.0 . . . . ? C14 C12 C13 O3 180.0 . . . . ? C11 C12 C14 C15 0.0 . . . . ? C13 C12 C14 C15 180.0 . . . . ? C12 C14 C15 C17 0.0 . . . . ? C12 C14 C15 C16 180.0 . . . . ? Co1 O5 C16 O6 0.0 6_656 . . . ? Co1 O5 C16 C15 180.0 6_656 . . . ? C14 C15 C16 O6 0.0 . . . . ? C17 C15 C16 O6 180.0 . . . . ? C14 C15 C16 O5 180.0 . . . . ? C17 C15 C16 O5 0.0 . . . . ? C11 C10 C17 C15 0.0 . . . . ? C9 C10 C17 C15 180.0 . . . . ? C14 C15 C17 C10 0.0 . . . . ? C16 C15 C17 C10 180.0 . . . . ? 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 O7 H2A O8 0.85 1.84 2.690(4) 176.6 . O3 H3 O7 0.82 1.84 2.580(4) 149.4 5_565 O7 H1A O6 0.85 1.80 2.651(4) 173.6 2_565 O8 H4 O4 0.85 2.14 2.969(5) 164.8 2_565 O8 H3C O2 0.85 1.89 2.724(4) 165.0 2_564 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.318 _refine_diff_density_min -0.248 _refine_diff_density_rms 0.053 #===end data_complex_4 _database_code_depnum_ccdc_archive 'CCDC 808520' #TrackingRef '- Revised cif-data.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H24 Co N6 O4' _chemical_formula_weight 519.42 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' O O 0.0106 0.0060 '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' Co Co 0.3494 0.9721 '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 4.9675(10) _cell_length_b 9.4623(19) _cell_length_c 11.725(2) _cell_angle_alpha 89.81(3) _cell_angle_beta 89.29(3) _cell_angle_gamma 79.03(3) _cell_volume 541.01(18) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1814 _cell_measurement_theta_min 2.1923 _cell_measurement_theta_max 27.9364 _exptl_crystal_description block _exptl_crystal_colour pink _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.594 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 269 _exptl_absorpt_coefficient_mu 0.841 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8499 _exptl_absorpt_correction_T_max 0.8914 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Rigaku Saturn' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3596 _diffrn_reflns_av_R_equivalents 0.0313 _diffrn_reflns_av_sigmaI/netI 0.0423 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 25.08 _reflns_number_total 1858 _reflns_number_gt 1749 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'CrystalStructure 3.7.0' _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^)+(0.0908P)^2^+2.5971P] 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 1858 _refine_ls_number_parameters 162 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0757 _refine_ls_R_factor_gt 0.0721 _refine_ls_wR_factor_ref 0.2034 _refine_ls_wR_factor_gt 0.2002 _refine_ls_goodness_of_fit_ref 1.182 _refine_ls_restrained_S_all 1.182 _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 Co1 Co 0.0000 0.5000 0.0000 0.0195(4) Uani 1 2 d S . . N1 N 0.1126(10) 0.4211(6) 0.1670(5) 0.0333(12) Uani 1 1 d . . . N2 N 0.3225(15) 0.3849(9) 0.3355(6) 0.065(2) Uani 1 1 d . . . N3 N 0.1175(11) 0.3088(6) 0.3308(5) 0.0395(14) Uani 1 1 d . . . C1 C 0.5603(12) 0.2973(6) -0.0334(5) 0.0271(13) Uani 1 1 d . . . C2 C 0.5264(11) 0.1433(6) -0.0107(5) 0.0237(12) Uani 1 1 d . . . C3 C 0.7043(12) 0.0512(7) 0.0553(6) 0.0307(13) Uani 1 1 d . . . H3 H 0.8448 0.0848 0.0918 0.037 Uiso 1 1 calc R . . C4 C 0.3193(12) 0.0908(7) -0.0692(6) 0.0312(14) Uani 1 1 d . . . H4 H 0.1999 0.1512 -0.1167 0.037 Uiso 1 1 calc R . . C5 C 0.3116(16) 0.4492(9) 0.2377(6) 0.0471(19) Uani 1 1 d . . . H5 H 0.4307 0.5100 0.2171 0.057 Uiso 1 1 calc R . . C6 C -0.0036(14) 0.3332(8) 0.2299(6) 0.0400(16) Uani 1 1 d . . . H6 H -0.1513 0.2934 0.2068 0.048 Uiso 1 1 calc R . . C7 C 0.0471(15) 0.2231(9) 0.4265(6) 0.0476(19) Uani 1 1 d . . . H7A H -0.1043 0.1778 0.4050 0.057 Uiso 1 1 calc R . . H7B H -0.0133 0.2863 0.4905 0.057 Uiso 1 1 calc R . . C8 C 0.2866(14) 0.1072(8) 0.4634(6) 0.0396(16) Uani 1 1 d . . . C9 C 0.4433(15) 0.1317(8) 0.5588(6) 0.0413(17) Uani 1 1 d . . . C10 C 0.385(2) 0.2761(10) 0.6207(8) 0.060(2) Uani 1 1 d . . . H10A H 0.2574 0.2722 0.6823 0.090 Uiso 1 1 calc R . . H10B H 0.3082 0.3507 0.5683 0.090 Uiso 1 1 calc R . . H10C H 0.5528 0.2963 0.6505 0.090 Uiso 1 1 calc R . . C11 C 0.3462(14) -0.0246(8) 0.4052(6) 0.0389(16) Uani 1 1 d . . . C12 C 0.1765(17) -0.0459(10) 0.3032(7) 0.054(2) Uani 1 1 d . . . H12A H 0.2584 -0.0141 0.2356 0.080 Uiso 1 1 calc R . . H12B H -0.0058 0.0090 0.3130 0.080 Uiso 1 1 calc R . . H12C H 0.1688 -0.1461 0.2961 0.080 Uiso 1 1 calc R . . O1 O 0.3619(8) 0.3836(4) -0.0738(4) 0.0297(10) Uani 1 1 d . . . O2 O 0.7925(8) 0.3248(4) -0.0090(4) 0.0319(10) 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 Co1 0.0244(6) 0.0127(5) 0.0224(6) 0.0032(4) -0.0043(4) -0.0056(4) N1 0.028(3) 0.029(3) 0.043(3) 0.012(2) -0.008(2) -0.006(2) N2 0.062(4) 0.094(6) 0.054(4) 0.029(4) -0.024(3) -0.051(4) N3 0.034(3) 0.046(3) 0.040(3) 0.017(3) -0.001(2) -0.014(3) C1 0.026(3) 0.021(3) 0.037(3) 0.004(2) 0.004(2) -0.009(2) C2 0.022(3) 0.014(3) 0.036(3) 0.001(2) 0.002(2) -0.005(2) C3 0.024(3) 0.030(3) 0.041(3) -0.003(3) -0.006(3) -0.009(2) C4 0.025(3) 0.029(3) 0.041(4) 0.011(3) -0.008(3) -0.008(2) C5 0.047(4) 0.063(5) 0.040(4) 0.018(3) -0.014(3) -0.032(4) C6 0.034(4) 0.046(4) 0.042(4) 0.020(3) -0.006(3) -0.012(3) C7 0.037(4) 0.068(5) 0.039(4) 0.024(4) 0.001(3) -0.013(4) C8 0.037(4) 0.048(4) 0.036(4) 0.017(3) -0.003(3) -0.014(3) C9 0.047(4) 0.046(4) 0.035(4) 0.011(3) 0.007(3) -0.022(3) C10 0.071(6) 0.057(5) 0.055(5) -0.001(4) -0.007(4) -0.018(4) C11 0.037(4) 0.058(4) 0.027(3) 0.016(3) -0.004(3) -0.025(3) C12 0.053(5) 0.074(6) 0.039(4) 0.008(4) -0.013(3) -0.024(4) O1 0.023(2) 0.025(2) 0.041(2) 0.0063(18) -0.0035(18) -0.0048(17) O2 0.024(2) 0.0149(19) 0.058(3) 0.0030(18) -0.0081(19) -0.0073(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 O1 2.099(4) . ? Co1 O1 2.099(4) 2_565 ? Co1 O2 2.116(4) 1_455 ? Co1 O2 2.116(4) 2_665 ? Co1 N1 2.136(5) . ? Co1 N1 2.136(5) 2_565 ? N1 C6 1.318(8) . ? N1 C5 1.363(9) . ? N2 C5 1.294(10) . ? N2 N3 1.357(8) . ? N3 C6 1.333(9) . ? N3 C7 1.459(9) . ? C1 O1 1.251(7) . ? C1 O2 1.267(7) . ? C1 C2 1.520(7) . ? C2 C3 1.364(9) . ? C2 C4 1.411(8) . ? C3 C4 1.380(9) 2_655 ? C3 H3 0.9300 . ? C4 C3 1.380(9) 2_655 ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.523(10) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C11 1.403(11) . ? C8 C9 1.415(10) . ? C9 C11 1.379(11) 2_656 ? C9 C10 1.526(11) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C9 1.379(11) 2_656 ? C11 C12 1.508(9) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? O2 Co1 2.116(4) 1_655 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Co1 O1 180 . 2_565 ? O1 Co1 O2 93.53(16) . 1_455 ? O1 Co1 O2 86.47(16) 2_565 1_455 ? O1 Co1 O2 86.47(16) . 2_665 ? O1 Co1 O2 93.53(16) 2_565 2_665 ? O2 Co1 O2 180 1_455 2_665 ? O1 Co1 N1 92.62(19) . . ? O1 Co1 N1 87.38(19) 2_565 . ? O2 Co1 N1 85.06(19) 1_455 . ? O2 Co1 N1 94.94(19) 2_665 . ? O1 Co1 N1 87.38(19) . 2_565 ? O1 Co1 N1 92.62(19) 2_565 2_565 ? O2 Co1 N1 94.94(19) 1_455 2_565 ? O2 Co1 N1 85.06(19) 2_665 2_565 ? N1 Co1 N1 180 . 2_565 ? C6 N1 C5 101.7(6) . . ? C6 N1 Co1 127.7(5) . . ? C5 N1 Co1 130.6(4) . . ? C5 N2 N3 103.6(6) . . ? C6 N3 N2 108.3(6) . . ? C6 N3 C7 129.1(6) . . ? N2 N3 C7 122.6(6) . . ? O1 C1 O2 126.4(5) . . ? O1 C1 C2 118.3(5) . . ? O2 C1 C2 115.3(5) . . ? C3 C2 C4 119.1(5) . . ? C3 C2 C1 122.3(5) . . ? C4 C2 C1 118.3(5) . . ? C2 C3 C4 121.6(6) . 2_655 ? C2 C3 H3 119.2 . . ? C4 C3 H3 119.2 2_655 . ? C3 C4 C2 119.3(6) 2_655 . ? C3 C4 H4 120.4 2_655 . ? C2 C4 H4 120.4 . . ? N2 C5 N1 115.0(6) . . ? N2 C5 H5 122.5 . . ? N1 C5 H5 122.5 . . ? N1 C6 N3 111.4(6) . . ? N1 C6 H6 124.3 . . ? N3 C6 H6 124.3 . . ? N3 C7 C8 112.7(6) . . ? N3 C7 H7A 109.0 . . ? C8 C7 H7A 109.0 . . ? N3 C7 H7B 109.0 . . ? C8 C7 H7B 109.0 . . ? H7A C7 H7B 107.8 . . ? C11 C8 C9 120.3(6) . . ? C11 C8 C7 120.1(6) . . ? C9 C8 C7 119.6(7) . . ? C11 C9 C8 119.5(7) 2_656 . ? C11 C9 C10 119.8(7) 2_656 . ? C8 C9 C10 120.7(7) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C11 C8 120.2(6) 2_656 . ? C9 C11 C12 121.1(7) 2_656 . ? C8 C11 C12 118.7(7) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C1 O1 Co1 132.6(4) . . ? C1 O2 Co1 140.7(4) . 1_655 ? 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 Co1 N1 C6 -112.1(6) . . . . ? O1 Co1 N1 C6 67.9(6) 2_565 . . . ? O2 Co1 N1 C6 -18.8(6) 1_455 . . . ? O2 Co1 N1 C6 161.2(6) 2_665 . . . ? N1 Co1 N1 C6 151(100) 2_565 . . . ? O1 Co1 N1 C5 70.0(7) . . . . ? O1 Co1 N1 C5 -110.0(7) 2_565 . . . ? O2 Co1 N1 C5 163.4(7) 1_455 . . . ? O2 Co1 N1 C5 -16.6(7) 2_665 . . . ? N1 Co1 N1 C5 -27(100) 2_565 . . . ? C5 N2 N3 C6 -0.2(10) . . . . ? C5 N2 N3 C7 -177.5(8) . . . . ? O1 C1 C2 C3 -165.2(6) . . . . ? O2 C1 C2 C3 14.9(9) . . . . ? O1 C1 C2 C4 21.1(8) . . . . ? O2 C1 C2 C4 -158.8(6) . . . . ? C4 C2 C3 C4 -2.2(10) . . . 2_655 ? C1 C2 C3 C4 -175.9(6) . . . 2_655 ? C3 C2 C4 C3 2.2(10) . . . 2_655 ? C1 C2 C4 C3 176.1(5) . . . 2_655 ? N3 N2 C5 N1 -0.2(11) . . . . ? C6 N1 C5 N2 0.4(10) . . . . ? Co1 N1 C5 N2 178.7(6) . . . . ? C5 N1 C6 N3 -0.5(8) . . . . ? Co1 N1 C6 N3 -178.9(4) . . . . ? N2 N3 C6 N1 0.5(9) . . . . ? C7 N3 C6 N1 177.5(7) . . . . ? C6 N3 C7 C8 124.6(8) . . . . ? N2 N3 C7 C8 -58.7(10) . . . . ? N3 C7 C8 C11 -82.5(8) . . . . ? N3 C7 C8 C9 99.3(8) . . . . ? C11 C8 C9 C11 -0.5(10) . . . 2_656 ? C7 C8 C9 C11 177.6(6) . . . 2_656 ? C11 C8 C9 C10 178.3(7) . . . . ? C7 C8 C9 C10 -3.5(9) . . . . ? C9 C8 C11 C9 0.5(10) . . . 2_656 ? C7 C8 C11 C9 -177.6(6) . . . 2_656 ? C9 C8 C11 C12 -179.3(6) . . . . ? C7 C8 C11 C12 2.5(9) . . . . ? O2 C1 O1 Co1 -101.4(7) . . . . ? C2 C1 O1 Co1 78.7(7) . . . . ? O1 Co1 O1 C1 97(100) 2_565 . . . ? O2 Co1 O1 C1 -82.9(5) 1_455 . . . ? O2 Co1 O1 C1 97.1(5) 2_665 . . . ? N1 Co1 O1 C1 2.3(5) . . . . ? N1 Co1 O1 C1 -177.7(5) 2_565 . . . ? O1 C1 O2 Co1 6.4(11) . . . 1_655 ? C2 C1 O2 Co1 -173.7(4) . . . 1_655 ? _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 25.08 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 0.936 _refine_diff_density_min -0.430 _refine_diff_density_rms 0.117 #===end data_ligand_btmx _database_code_depnum_ccdc_archive 'CCDC 808579' #TrackingRef '- Revised cif-data.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H20 N6' _chemical_formula_weight 296.38 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 4.4497(9) _cell_length_b 8.1310(16) _cell_length_c 21.526(5) _cell_angle_alpha 90.00 _cell_angle_beta 101.42(3) _cell_angle_gamma 90.00 _cell_volume 763.4(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2021 _cell_measurement_theta_min 1.9303 _cell_measurement_theta_max 27.8892 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.289 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 316 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9805 _exptl_absorpt_correction_T_max 0.9853 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Rigaku Saturn' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4941 _diffrn_reflns_av_R_equivalents 0.0382 _diffrn_reflns_av_sigmaI/netI 0.0317 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1341 _reflns_number_gt 1132 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'CrystalStructure 3.7.0' _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^)+(0.1296P)^2^+0.1443P] 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 1341 _refine_ls_number_parameters 102 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0896 _refine_ls_R_factor_gt 0.0738 _refine_ls_wR_factor_ref 0.2396 _refine_ls_wR_factor_gt 0.2176 _refine_ls_goodness_of_fit_ref 1.190 _refine_ls_restrained_S_all 1.190 _refine_ls_shift/su_max 0.006 _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 0.5114(6) 0.2812(3) 0.84704(11) 0.0541(8) Uani 1 1 d . . . N2 N 0.3663(7) 0.1478(3) 0.86425(13) 0.0688(9) Uani 1 1 d . . . N3 N 0.2197(9) 0.1921(5) 0.76061(15) 0.0938(12) Uani 1 1 d . . . C1 C 0.1940(9) 0.1019(5) 0.80997(17) 0.0710(10) Uani 1 1 d . . . H1 H 0.0632 0.0118 0.8068 0.085 Uiso 1 1 calc R . . C2 C 0.4223(11) 0.3031(6) 0.78612(18) 0.0907(13) Uani 1 1 d . . . H2 H 0.4934 0.3871 0.7635 0.109 Uiso 1 1 calc R . . C3 C 0.7393(7) 0.3730(4) 0.89310(15) 0.0616(9) Uani 1 1 d . . . H3A H 0.8146 0.4646 0.8717 0.074 Uiso 1 1 calc R . . H3B H 0.9117 0.3015 0.9091 0.074 Uiso 1 1 calc R . . C4 C 0.6102(6) 0.4383(3) 0.94868(13) 0.0469(8) Uani 1 1 d . . . C5 C 0.6564(6) 0.3484(3) 1.00530(13) 0.0469(8) Uani 1 1 d . . . C6 C 0.4537(6) 0.5885(3) 0.94294(13) 0.0478(8) Uani 1 1 d . . . C7 C 0.4019(10) 0.6858(4) 0.88120(17) 0.0764(11) Uani 1 1 d . . . H7A H 0.5124 0.6349 0.8523 0.115 Uiso 1 1 calc R . . H7B H 0.4738 0.7964 0.8897 0.115 Uiso 1 1 calc R . . H7C H 0.1870 0.6873 0.8628 0.115 Uiso 1 1 calc R . . C8 C 0.8215(8) 0.1836(4) 1.01035(18) 0.0693(10) Uani 1 1 d . . . H8A H 0.7666 0.1257 0.9708 0.104 Uiso 1 1 calc R . . H8B H 0.7632 0.1195 1.0435 0.104 Uiso 1 1 calc R . . H8C H 1.0391 0.2015 1.0199 0.104 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 N1 0.0570(15) 0.0523(15) 0.0564(16) -0.0074(11) 0.0194(12) -0.0019(12) N2 0.085(2) 0.0568(16) 0.0647(18) -0.0070(13) 0.0144(15) -0.0139(15) N3 0.107(3) 0.108(3) 0.0593(19) -0.0094(19) 0.0001(18) -0.018(2) C1 0.078(2) 0.064(2) 0.069(2) -0.0219(18) 0.0079(17) -0.0082(18) C2 0.114(3) 0.099(3) 0.058(2) 0.015(2) 0.013(2) -0.024(3) C3 0.0522(18) 0.0654(19) 0.071(2) -0.0157(16) 0.0214(15) -0.0111(15) C4 0.0431(14) 0.0427(15) 0.0542(17) -0.0104(12) 0.0080(12) -0.0054(12) C5 0.0418(14) 0.0362(14) 0.0594(18) -0.0028(12) 0.0020(12) 0.0010(11) C6 0.0475(16) 0.0412(15) 0.0522(17) -0.0006(12) 0.0033(12) -0.0059(12) C7 0.099(3) 0.062(2) 0.063(2) 0.0105(17) 0.0031(18) -0.0035(19) C8 0.065(2) 0.0493(18) 0.088(2) -0.0071(17) -0.0008(18) 0.0109(16) _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 1.305(4) . ? N1 N2 1.351(4) . ? N1 C3 1.473(4) . ? N2 C1 1.318(4) . ? N3 C2 1.317(5) . ? N3 C1 1.315(5) . ? C1 H1 0.9300 . ? C2 H2 0.9300 . ? C3 C4 1.521(4) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C6 1.399(4) . ? C4 C5 1.401(4) . ? C5 C6 1.401(4) 3_667 ? C5 C8 1.522(4) . ? C6 C5 1.401(4) 3_667 ? C6 C7 1.524(4) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 N2 108.6(3) . . ? C2 N1 C3 129.7(3) . . ? N2 N1 C3 121.7(3) . . ? C1 N2 N1 102.1(3) . . ? C2 N3 C1 102.0(3) . . ? N2 C1 N3 115.5(3) . . ? N2 C1 H1 122.3 . . ? N3 C1 H1 122.3 . . ? N1 C2 N3 111.8(4) . . ? N1 C2 H2 124.1 . . ? N3 C2 H2 124.1 . . ? N1 C3 C4 112.9(2) . . ? N1 C3 H3A 109.0 . . ? C4 C3 H3A 109.0 . . ? N1 C3 H3B 109.0 . . ? C4 C3 H3B 109.0 . . ? H3A C3 H3B 107.8 . . ? C6 C4 C5 121.1(2) . . ? C6 C4 C3 119.6(3) . . ? C5 C4 C3 119.2(3) . . ? C6 C5 C4 119.1(2) 3_667 . ? C6 C5 C8 120.4(3) 3_667 . ? C4 C5 C8 120.5(3) . . ? C4 C6 C5 119.7(2) . 3_667 ? C4 C6 C7 121.1(3) . . ? C5 C6 C7 119.2(3) 3_667 . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C5 C8 H8A 109.5 . . ? C5 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C5 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? 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 N2 C1 -0.8(4) . . . . ? C3 N1 N2 C1 -178.3(3) . . . . ? N1 N2 C1 N3 0.7(4) . . . . ? C2 N3 C1 N2 -0.3(5) . . . . ? N2 N1 C2 N3 0.7(5) . . . . ? C3 N1 C2 N3 178.0(3) . . . . ? C1 N3 C2 N1 -0.3(5) . . . . ? C2 N1 C3 C4 125.0(4) . . . . ? N2 N1 C3 C4 -58.0(4) . . . . ? N1 C3 C4 C6 -84.7(3) . . . . ? N1 C3 C4 C5 96.7(3) . . . . ? C6 C4 C5 C6 -0.7(4) . . . 3_667 ? C3 C4 C5 C6 177.9(2) . . . 3_667 ? C6 C4 C5 C8 178.8(3) . . . . ? C3 C4 C5 C8 -2.7(4) . . . . ? C5 C4 C6 C5 0.7(4) . . . 3_667 ? C3 C4 C6 C5 -177.9(2) . . . 3_667 ? C5 C4 C6 C7 -179.6(3) . . . . ? C3 C4 C6 C7 1.8(4) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.208 _refine_diff_density_min -0.177 _refine_diff_density_rms 0.046 #===end