# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Pradyut Ghosh' _publ_contact_author_email ICPG@IACS.RES.IN _publ_section_title ; Nitrate directed organized assemblies of protonated arene based tripodal receptors ; loop_ _publ_author_name 'Pradyut Ghosh' 'M Arunachalam' # Attachment 'Complex-_5.cif' data_Complex-5 _database_code_depnum_ccdc_archive 'CCDC 747559' #TrackingRef 'Complex-_5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H20 N4, H N2 O6, N O3' _chemical_formula_sum 'C22 H21 N7 O9' _chemical_formula_weight 527.46 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 10.6360(18) _cell_length_b 18.174(3) _cell_length_c 12.645(2) _cell_angle_alpha 90.00 _cell_angle_beta 104.343(2) _cell_angle_gamma 90.00 _cell_volume 2368.1(7) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2402 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 20.84 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.479 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1096 _exptl_absorpt_coefficient_mu 0.118 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9769 _exptl_absorpt_correction_T_max 0.9837 _exptl_absorpt_process_details SADABS _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 'CCD area detector' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean 3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17067 _diffrn_reflns_av_R_equivalents 0.0545 _diffrn_reflns_av_sigmaI/netI 0.0358 _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 -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 21.98 _reflns_number_total 2897 _reflns_number_gt 2255 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'PLATON Spek, 2009' _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^)+(0.0475P)^2^+1.2339P] 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 0.0013(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2897 _refine_ls_number_parameters 351 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0566 _refine_ls_R_factor_gt 0.0403 _refine_ls_wR_factor_ref 0.1012 _refine_ls_wR_factor_gt 0.0925 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.033 _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 N14 N 0.6960(2) 0.04837(12) 0.54468(18) 0.0284(6) Uani 1 1 d . . . H14 H 0.6962 0.0021 0.5241 0.034 Uiso 1 1 calc R . . N21 N 0.6599(2) 0.14594(11) 0.63322(17) 0.0218(5) Uani 1 1 d . . . N30 N 0.1030(2) 0.27184(12) 0.65399(17) 0.0255(6) Uani 1 1 d . . . N32 N 0.0178(2) 0.30576(12) 0.78653(18) 0.0268(6) Uani 1 1 d . . . H32 H -0.0118 0.3342 0.8313 0.032 Uiso 1 1 calc R . . C13 C 0.6429(3) 0.07364(14) 0.6216(2) 0.0262(7) Uani 1 1 d . . . H13 H 0.5987 0.0442 0.6629 0.031 Uiso 1 1 calc R . . C15 C 0.7511(3) 0.10652(14) 0.5018(2) 0.0252(7) Uani 1 1 d . . . C16 C 0.8195(3) 0.10978(16) 0.4217(2) 0.0297(7) Uani 1 1 d . . . H16 H 0.8366 0.0669 0.3847 0.036 Uiso 1 1 calc R . . C17 C 0.8615(3) 0.17828(16) 0.3986(2) 0.0322(7) Uani 1 1 d . . . H17 H 0.9088 0.1826 0.3443 0.039 Uiso 1 1 calc R . . C18 C 0.8366(3) 0.24139(16) 0.4526(2) 0.0295(7) Uani 1 1 d . . . H18 H 0.8661 0.2876 0.4333 0.035 Uiso 1 1 calc R . . C19 C 0.7703(3) 0.23859(15) 0.5335(2) 0.0266(7) Uani 1 1 d . . . H19 H 0.7541 0.2816 0.5707 0.032 Uiso 1 1 calc R . . C20 C 0.7283(2) 0.16931(14) 0.5578(2) 0.0216(6) Uani 1 1 d . . . C22 C 0.6253(3) 0.19046(14) 0.7196(2) 0.0256(7) Uani 1 1 d . . . H22A H 0.7053 0.2127 0.7655 0.031 Uiso 1 1 calc R . . H22B H 0.5886 0.1575 0.7667 0.031 Uiso 1 1 calc R . . C23 C 0.5289(3) 0.25103(14) 0.6771(2) 0.0229(7) Uani 1 1 d . . . C24 C 0.5710(3) 0.32328(14) 0.6790(2) 0.0270(7) Uani 1 1 d . . . H24 H 0.6607 0.3341 0.7054 0.032 Uiso 1 1 calc R . . C25 C 0.4843(3) 0.37936(15) 0.6429(2) 0.0314(7) Uani 1 1 d . . . H25 H 0.5145 0.4286 0.6442 0.038 Uiso 1 1 calc R . . C26 C 0.3537(3) 0.36452(15) 0.6047(2) 0.0316(7) Uani 1 1 d . . . H26 H 0.2943 0.4036 0.5803 0.038 Uiso 1 1 calc R . . C27 C 0.3087(3) 0.29275(15) 0.6019(2) 0.0261(7) Uani 1 1 d . . . C28 C 0.3972(3) 0.23594(15) 0.6391(2) 0.0243(7) Uani 1 1 d . . . H28 H 0.3672 0.1867 0.6385 0.029 Uiso 1 1 calc R . . C29 C 0.1653(3) 0.27699(16) 0.5624(2) 0.0307(7) Uani 1 1 d . . . H29A H 0.1235 0.3167 0.5123 0.037 Uiso 1 1 calc R . . H29B H 0.1527 0.2301 0.5211 0.037 Uiso 1 1 calc R . . C31 C 0.0678(3) 0.32882(16) 0.7063(2) 0.0287(7) Uani 1 1 d . . . H31 H 0.0772 0.3790 0.6886 0.034 Uiso 1 1 calc R . . C33 C 0.0198(3) 0.22957(14) 0.7883(2) 0.0253(7) Uani 1 1 d . . . C34 C -0.0205(3) 0.17850(15) 0.8552(2) 0.0309(7) Uani 1 1 d . . . H34 H -0.0557 0.1933 0.9140 0.037 Uiso 1 1 calc R . . C35 C -0.0067(3) 0.10587(16) 0.8320(3) 0.0416(8) Uani 1 1 d . . . H35 H -0.0344 0.0694 0.8751 0.050 Uiso 1 1 calc R . . C36 C 0.0472(3) 0.08358(16) 0.7462(3) 0.0442(9) Uani 1 1 d . . . H36 H 0.0551 0.0325 0.7331 0.053 Uiso 1 1 calc R . . C37 C 0.0891(3) 0.13394(16) 0.6803(2) 0.0360(8) Uani 1 1 d . . . H37 H 0.1261 0.1190 0.6227 0.043 Uiso 1 1 calc R . . C38 C 0.0737(3) 0.20757(15) 0.7034(2) 0.0256(7) Uani 1 1 d . . . N1 N 0.8136(3) 0.46922(18) 0.6139(3) 0.0356(9) Uani 0.883(4) 1 d PD . . N1A N 0.7820(18) 0.4579(10) 0.5983(9) 0.0356(9) Uani 0.117(4) 1 d PD . . O11 O 0.8398(2) 0.42581(11) 0.53835(18) 0.0502(6) Uani 1 1 d D . . H12 H 0.8519 0.4641 0.4603 0.075 Uiso 1 1 d R . . O12 O 0.7982(2) 0.43955(12) 0.69544(18) 0.0563(7) Uani 1 1 d D . . O13 O 0.8101(3) 0.53544(14) 0.59859(19) 0.0481(8) Uani 0.883(4) 1 d PD . . O13A O 0.7036(17) 0.5060(9) 0.5556(10) 0.0481(8) Uani 0.117(4) 1 d PD . . N2 N 0.8979(2) 0.46148(15) 0.3104(2) 0.0364(6) Uani 1 1 d . . . O21 O 0.8637(2) 0.50224(11) 0.38204(17) 0.0442(6) Uani 1 1 d . . . O22 O 0.9137(2) 0.49125(12) 0.22755(19) 0.0490(6) Uani 1 1 d . . . O23 O 0.9113(2) 0.39544(12) 0.3279(2) 0.0622(7) Uani 1 1 d . . . N3 N -0.1824(2) 0.36833(13) 0.93124(18) 0.0267(6) Uani 1 1 d . . . O31 O -0.07802(19) 0.39891(10) 0.92375(15) 0.0322(5) Uani 1 1 d . . . O32 O -0.20931(19) 0.30569(10) 0.89454(15) 0.0336(5) Uani 1 1 d . . . O33 O -0.25695(19) 0.40248(10) 0.97742(16) 0.0348(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N14 0.0403(15) 0.0171(13) 0.0310(14) -0.0030(11) 0.0150(12) -0.0008(11) N21 0.0253(14) 0.0193(14) 0.0224(13) -0.0004(10) 0.0087(11) 0.0007(10) N30 0.0249(14) 0.0287(14) 0.0252(13) 0.0000(11) 0.0103(11) 0.0029(11) N32 0.0304(14) 0.0251(14) 0.0282(14) 0.0004(11) 0.0137(11) 0.0053(11) C13 0.0313(17) 0.0202(17) 0.0281(17) 0.0032(13) 0.0093(14) -0.0022(13) C15 0.0280(16) 0.0207(15) 0.0263(16) 0.0019(13) 0.0054(13) -0.0026(13) C16 0.0330(18) 0.0317(18) 0.0269(17) -0.0054(14) 0.0121(14) 0.0007(14) C17 0.0316(18) 0.0416(19) 0.0265(17) 0.0026(15) 0.0131(14) -0.0036(15) C18 0.0289(17) 0.0288(17) 0.0306(17) 0.0057(14) 0.0074(14) -0.0051(13) C19 0.0288(17) 0.0242(16) 0.0265(16) -0.0009(13) 0.0061(14) -0.0016(13) C20 0.0201(15) 0.0237(16) 0.0217(16) 0.0022(13) 0.0064(12) 0.0001(12) C22 0.0310(17) 0.0250(16) 0.0222(15) -0.0005(13) 0.0092(13) 0.0012(13) C23 0.0279(17) 0.0231(16) 0.0192(15) -0.0020(12) 0.0088(13) -0.0005(13) C24 0.0297(17) 0.0249(17) 0.0279(17) -0.0038(13) 0.0099(13) -0.0018(14) C25 0.042(2) 0.0216(16) 0.0354(18) -0.0015(14) 0.0186(15) -0.0016(15) C26 0.041(2) 0.0258(18) 0.0324(18) 0.0066(13) 0.0171(15) 0.0128(15) C27 0.0320(18) 0.0288(17) 0.0204(16) 0.0020(13) 0.0119(13) 0.0057(14) C28 0.0330(19) 0.0227(16) 0.0197(15) -0.0004(12) 0.0114(13) -0.0010(13) C29 0.0308(18) 0.0400(18) 0.0241(16) 0.0049(14) 0.0121(14) 0.0042(14) C31 0.0253(17) 0.0284(17) 0.0326(18) 0.0051(14) 0.0078(14) 0.0024(13) C33 0.0239(16) 0.0249(17) 0.0269(17) -0.0001(13) 0.0056(13) 0.0028(13) C34 0.0303(18) 0.0320(18) 0.0334(18) 0.0043(14) 0.0135(14) 0.0054(14) C35 0.054(2) 0.0289(19) 0.051(2) 0.0108(16) 0.0302(18) 0.0059(16) C36 0.055(2) 0.0234(17) 0.062(2) 0.0024(16) 0.0296(19) 0.0039(15) C37 0.0389(19) 0.0332(19) 0.0402(19) -0.0033(15) 0.0182(16) 0.0041(15) C38 0.0222(16) 0.0248(17) 0.0304(17) 0.0033(13) 0.0075(13) 0.0021(13) N1 0.035(2) 0.037(2) 0.0328(18) 0.0019(16) 0.0047(14) -0.0101(15) N1A 0.035(2) 0.037(2) 0.0328(18) 0.0019(16) 0.0047(14) -0.0101(15) O11 0.0812(18) 0.0291(12) 0.0446(14) -0.0011(11) 0.0238(13) 0.0031(11) O12 0.0762(18) 0.0570(15) 0.0345(14) 0.0014(12) 0.0114(12) -0.0292(13) O13 0.072(2) 0.0336(17) 0.0380(16) 0.0048(12) 0.0121(14) 0.0152(14) O13A 0.072(2) 0.0336(17) 0.0380(16) 0.0048(12) 0.0121(14) 0.0152(14) N2 0.0382(16) 0.0310(17) 0.0445(18) -0.0069(14) 0.0189(13) -0.0005(12) O21 0.0670(16) 0.0287(12) 0.0459(13) 0.0000(11) 0.0312(12) 0.0096(11) O22 0.0554(16) 0.0531(15) 0.0473(15) 0.0071(12) 0.0290(12) 0.0085(12) O23 0.094(2) 0.0254(14) 0.0863(19) -0.0026(12) 0.0584(16) 0.0058(12) N3 0.0348(16) 0.0238(15) 0.0220(13) 0.0041(11) 0.0076(12) 0.0007(13) O31 0.0353(13) 0.0288(11) 0.0354(12) -0.0029(9) 0.0145(10) -0.0045(10) O32 0.0460(13) 0.0217(12) 0.0335(12) -0.0061(9) 0.0109(10) -0.0063(10) O33 0.0462(13) 0.0258(11) 0.0412(13) -0.0006(10) 0.0276(11) 0.0043(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 N14 C13 1.321(3) . ? N14 C15 1.383(3) . ? N14 H14 0.8800 . ? N21 C13 1.330(3) . ? N21 C20 1.401(3) . ? N21 C22 1.477(3) . ? N30 C31 1.332(3) . ? N30 C38 1.396(3) . ? N30 C29 1.473(3) . ? N32 C31 1.324(3) . ? N32 C33 1.385(3) . ? N32 H32 0.8800 . ? C13 H13 0.9500 . ? C15 C16 1.387(4) . ? C15 C20 1.396(4) . ? C16 C17 1.378(4) . ? C16 H16 0.9500 . ? C17 C18 1.394(4) . ? C17 H17 0.9500 . ? C18 C19 1.379(4) . ? C18 H18 0.9500 . ? C19 C20 1.396(4) . ? C19 H19 0.9500 . ? C22 C23 1.509(4) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C24 1.386(4) . ? C23 C28 1.391(4) . ? C24 C25 1.374(4) . ? C24 H24 0.9500 . ? C25 C26 1.380(4) . ? C25 H25 0.9500 . ? C26 C27 1.387(4) . ? C26 H26 0.9500 . ? C27 C28 1.398(4) . ? C27 C29 1.510(4) . ? C28 H28 0.9500 . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C31 H31 0.9500 . ? C33 C34 1.393(4) . ? C33 C38 1.396(4) . ? C34 C35 1.368(4) . ? C34 H34 0.9500 . ? C35 C36 1.406(4) . ? C35 H35 0.9500 . ? C36 C37 1.384(4) . ? C36 H36 0.9500 . ? C37 C38 1.388(4) . ? C37 H37 0.9500 . ? N1 O12 1.210(3) . ? N1 O13 1.218(4) . ? N1 O11 1.321(4) . ? N1A O11 1.235(9) . ? N1A O13A 1.235(9) . ? N1A O12 1.243(9) . ? O11 H12 1.2406 . ? O13 O13A 1.25(2) . ? N2 O23 1.222(3) . ? N2 O22 1.227(3) . ? N2 O21 1.290(3) . ? O21 H12 1.2395 . ? N3 O32 1.236(3) . ? N3 O33 1.258(3) . ? N3 O31 1.266(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 C13 N14 C15 108.8(2) . . ? C13 N14 H14 125.6 . . ? C15 N14 H14 125.6 . . ? C13 N21 C20 107.6(2) . . ? C13 N21 C22 124.9(2) . . ? C20 N21 C22 127.1(2) . . ? C31 N30 C38 107.9(2) . . ? C31 N30 C29 125.3(2) . . ? C38 N30 C29 126.8(2) . . ? C31 N32 C33 108.8(2) . . ? C31 N32 H32 125.6 . . ? C33 N32 H32 125.6 . . ? N14 C13 N21 110.7(2) . . ? N14 C13 H13 124.6 . . ? N21 C13 H13 124.6 . . ? N14 C15 C16 132.0(2) . . ? N14 C15 C20 106.4(2) . . ? C16 C15 C20 121.6(2) . . ? C17 C16 C15 116.7(3) . . ? C17 C16 H16 121.6 . . ? C15 C16 H16 121.6 . . ? C16 C17 C18 121.9(3) . . ? C16 C17 H17 119.1 . . ? C18 C17 H17 119.1 . . ? C19 C18 C17 121.8(3) . . ? C19 C18 H18 119.1 . . ? C17 C18 H18 119.1 . . ? C18 C19 C20 116.6(3) . . ? C18 C19 H19 121.7 . . ? C20 C19 H19 121.7 . . ? C19 C20 C15 121.3(2) . . ? C19 C20 N21 132.2(2) . . ? C15 C20 N21 106.4(2) . . ? N21 C22 C23 114.1(2) . . ? N21 C22 H22A 108.7 . . ? C23 C22 H22A 108.7 . . ? N21 C22 H22B 108.7 . . ? C23 C22 H22B 108.7 . . ? H22A C22 H22B 107.6 . . ? C24 C23 C28 119.1(2) . . ? C24 C23 C22 119.8(2) . . ? C28 C23 C22 121.1(2) . . ? C25 C24 C23 120.6(3) . . ? C25 C24 H24 119.7 . . ? C23 C24 H24 119.7 . . ? C24 C25 C26 120.4(3) . . ? C24 C25 H25 119.8 . . ? C26 C25 H25 119.8 . . ? C25 C26 C27 120.3(3) . . ? C25 C26 H26 119.9 . . ? C27 C26 H26 119.9 . . ? C26 C27 C28 119.1(3) . . ? C26 C27 C29 120.0(2) . . ? C28 C27 C29 120.8(2) . . ? C23 C28 C27 120.5(2) . . ? C23 C28 H28 119.8 . . ? C27 C28 H28 119.8 . . ? N30 C29 C27 111.5(2) . . ? N30 C29 H29A 109.3 . . ? C27 C29 H29A 109.3 . . ? N30 C29 H29B 109.3 . . ? C27 C29 H29B 109.3 . . ? H29A C29 H29B 108.0 . . ? N32 C31 N30 110.5(2) . . ? N32 C31 H31 124.8 . . ? N30 C31 H31 124.8 . . ? N32 C33 C34 132.1(3) . . ? N32 C33 C38 106.3(2) . . ? C34 C33 C38 121.5(2) . . ? C35 C34 C33 116.6(3) . . ? C35 C34 H34 121.7 . . ? C33 C34 H34 121.7 . . ? C34 C35 C36 122.0(3) . . ? C34 C35 H35 119.0 . . ? C36 C35 H35 119.0 . . ? C37 C36 C35 121.8(3) . . ? C37 C36 H36 119.1 . . ? C35 C36 H36 119.1 . . ? C36 C37 C38 116.0(3) . . ? C36 C37 H37 122.0 . . ? C38 C37 H37 122.0 . . ? C37 C38 C33 122.0(3) . . ? C37 C38 N30 131.4(3) . . ? C33 C38 N30 106.5(2) . . ? O12 N1 O13 124.8(3) . . ? O12 N1 O11 116.6(3) . . ? O13 N1 O11 118.6(3) . . ? O11 N1A O13A 116.7(9) . . ? O11 N1A O12 120.8(8) . . ? O13A N1A O12 122.4(9) . . ? N1A O11 H12 112.9 . . ? N1 O11 H12 108.8 . . ? O23 N2 O22 123.6(3) . . ? O23 N2 O21 118.5(3) . . ? O22 N2 O21 117.9(2) . . ? N2 O21 H12 109.9 . . ? O32 N3 O33 121.0(2) . . ? O32 N3 O31 120.1(2) . . ? O33 N3 O31 118.9(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 C15 N14 C13 N21 -0.3(3) . . . . ? C20 N21 C13 N14 0.4(3) . . . . ? C22 N21 C13 N14 -173.1(2) . . . . ? C13 N14 C15 C16 178.8(3) . . . . ? C13 N14 C15 C20 0.0(3) . . . . ? N14 C15 C16 C17 -179.9(3) . . . . ? C20 C15 C16 C17 -1.3(4) . . . . ? C15 C16 C17 C18 -0.1(4) . . . . ? C16 C17 C18 C19 1.1(4) . . . . ? C17 C18 C19 C20 -0.6(4) . . . . ? C18 C19 C20 C15 -0.8(4) . . . . ? C18 C19 C20 N21 179.9(3) . . . . ? N14 C15 C20 C19 -179.2(2) . . . . ? C16 C15 C20 C19 1.8(4) . . . . ? N14 C15 C20 N21 0.2(3) . . . . ? C16 C15 C20 N21 -178.8(2) . . . . ? C13 N21 C20 C19 179.0(3) . . . . ? C22 N21 C20 C19 -7.7(4) . . . . ? C13 N21 C20 C15 -0.4(3) . . . . ? C22 N21 C20 C15 173.0(2) . . . . ? C13 N21 C22 C23 -121.1(3) . . . . ? C20 N21 C22 C23 66.7(3) . . . . ? N21 C22 C23 C24 -103.9(3) . . . . ? N21 C22 C23 C28 78.2(3) . . . . ? C28 C23 C24 C25 -0.6(4) . . . . ? C22 C23 C24 C25 -178.6(2) . . . . ? C23 C24 C25 C26 0.4(4) . . . . ? C24 C25 C26 C27 -0.4(4) . . . . ? C25 C26 C27 C28 0.6(4) . . . . ? C25 C26 C27 C29 178.7(2) . . . . ? C24 C23 C28 C27 0.9(4) . . . . ? C22 C23 C28 C27 178.8(2) . . . . ? C26 C27 C28 C23 -0.9(4) . . . . ? C29 C27 C28 C23 -178.9(2) . . . . ? C31 N30 C29 C27 79.5(3) . . . . ? C38 N30 C29 C27 -98.5(3) . . . . ? C26 C27 C29 N30 -95.4(3) . . . . ? C28 C27 C29 N30 82.6(3) . . . . ? C33 N32 C31 N30 0.1(3) . . . . ? C38 N30 C31 N32 0.1(3) . . . . ? C29 N30 C31 N32 -178.2(2) . . . . ? C31 N32 C33 C34 180.0(3) . . . . ? C31 N32 C33 C38 -0.3(3) . . . . ? N32 C33 C34 C35 178.5(3) . . . . ? C38 C33 C34 C35 -1.2(4) . . . . ? C33 C34 C35 C36 1.0(5) . . . . ? C34 C35 C36 C37 -0.1(5) . . . . ? C35 C36 C37 C38 -0.5(5) . . . . ? C36 C37 C38 C33 0.3(4) . . . . ? C36 C37 C38 N30 -179.1(3) . . . . ? N32 C33 C38 C37 -179.1(3) . . . . ? C34 C33 C38 C37 0.6(4) . . . . ? N32 C33 C38 N30 0.4(3) . . . . ? C34 C33 C38 N30 -179.9(2) . . . . ? C31 N30 C38 C37 179.2(3) . . . . ? C29 N30 C38 C37 -2.6(5) . . . . ? C31 N30 C38 C33 -0.3(3) . . . . ? C29 N30 C38 C33 178.0(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 N14 H14 O33 0.88 1.92 2.760(3) 158 2_546 N32 H32 O31 0.88 1.91 2.791(3) 178 . O11 H12 O21 1.24 1.24 2.480(3) 180 . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 21.98 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.395 _refine_diff_density_min -0.296 _refine_diff_density_rms 0.043 # Attachment 'Complex_4.cif' data_tdmpyn _database_code_depnum_ccdc_archive 'CCDC 747560' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H39 N9 O9' _chemical_formula_weight 633.67 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 11.363(5) _cell_length_b 12.402(5) _cell_length_c 13.447(9) _cell_angle_alpha 111.290(14) _cell_angle_beta 106.240(14) _cell_angle_gamma 101.630(10) _cell_volume 1594.9(14) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1994 _cell_measurement_theta_min 2.22 _cell_measurement_theta_max 19.41 _exptl_crystal_description Block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.319 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9762 _exptl_absorpt_correction_T_max 0.9860 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _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 'CCD area detector' _diffrn_measurement_method 'phi scan' _diffrn_detector_area_resol_mean 3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12374 _diffrn_reflns_av_R_equivalents 0.0382 _diffrn_reflns_av_sigmaI/netI 0.0431 _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 -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 22.72 _reflns_number_total 4264 _reflns_number_gt 2825 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0825P)^2^+0.3992P] 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 4264 _refine_ls_number_parameters 415 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0853 _refine_ls_R_factor_gt 0.0542 _refine_ls_wR_factor_ref 0.1625 _refine_ls_wR_factor_gt 0.1409 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 O1 O 0.0581(4) 0.1497(3) 0.8991(3) 0.1234(12) Uani 1 1 d . . . N2 N 0.1029(4) 0.0706(4) 0.9067(3) 0.0876(11) Uani 1 1 d . . . O3 O 0.0545(3) -0.0364(3) 0.8209(2) 0.0801(8) Uani 1 1 d . . . O4 O 0.1933(4) 0.0882(4) 0.9927(3) 0.1611(18) Uani 1 1 d . . . O5 O 0.1558(2) 0.8658(2) 0.6029(2) 0.0639(6) Uani 1 1 d . . . N6 N 0.1835(3) 0.8158(3) 0.5157(3) 0.0635(8) Uani 1 1 d . . . O7 O 0.2816(3) 0.7868(3) 0.5308(3) 0.1048(10) Uani 1 1 d . . . O8 O 0.1126(3) 0.8016(2) 0.4212(2) 0.0833(8) Uani 1 1 d . . . O9 O 0.7413(4) 0.5723(4) 0.4232(3) 0.1379(14) Uani 1 1 d . . . N10 N 0.8396(4) 0.5687(3) 0.4053(4) 0.0804(10) Uani 1 1 d . . . O11 O 0.9447(3) 0.6009(3) 0.4867(3) 0.1056(10) Uani 1 1 d . . . O12 O 0.8404(3) 0.5359(3) 0.3077(3) 0.1018(10) Uani 1 1 d . . . C13 C 0.8109(4) 0.8071(4) 0.3120(3) 0.0757(11) Uani 1 1 d . . . H13A H 0.8898 0.7885 0.3176 0.113 Uiso 1 1 calc R . . H13B H 0.8070 0.8635 0.2786 0.113 Uiso 1 1 calc R . . H13C H 0.7373 0.7327 0.2640 0.113 Uiso 1 1 calc R . . C14 C 0.8088(3) 0.8634(3) 0.4286(3) 0.0509(8) Uani 1 1 d . . . N15 N 0.9110(2) 0.8892(2) 0.5229(2) 0.0548(7) Uani 1 1 d . . . H15 H 0.9819 0.8750 0.5225 0.066 Uiso 1 1 calc R . . N16 N 0.8868(3) 0.9400(2) 0.6173(2) 0.0569(7) Uani 1 1 d . . . H16 H 0.9393 0.9637 0.6871 0.068 Uiso 1 1 calc R . . C17 C 0.7677(3) 0.9481(3) 0.5859(3) 0.0534(8) Uani 1 1 d . . . C18 C 0.7144(4) 1.0023(4) 0.6743(3) 0.0854(12) Uani 1 1 d . . . H18A H 0.7724 1.0173 0.7489 0.128 Uiso 1 1 calc R . . H18B H 0.6305 0.9461 0.6546 0.128 Uiso 1 1 calc R . . H18C H 0.7058 1.0784 0.6763 0.128 Uiso 1 1 calc R . . C19 C 0.7145(3) 0.9002(3) 0.4667(3) 0.0491(8) Uani 1 1 d . . . C20 C 0.5815(3) 0.8945(3) 0.3967(3) 0.0610(9) Uani 1 1 d . . . H20A H 0.5917 0.9671 0.3835 0.073 Uiso 1 1 calc R . . H20B H 0.5286 0.8979 0.4425 0.073 Uiso 1 1 calc R . . C21 C 0.5081(3) 0.7813(3) 0.2802(3) 0.0481(8) Uani 1 1 d . . . C22 C 0.4717(3) 0.6596(3) 0.3906(3) 0.0638(10) Uani 1 1 d . . . H22A H 0.5557 0.7159 0.4478 0.096 Uiso 1 1 calc R . . H22B H 0.4667 0.5772 0.3780 0.096 Uiso 1 1 calc R . . H22C H 0.4052 0.6797 0.4172 0.096 Uiso 1 1 calc R . . C23 C 0.4517(3) 0.6691(3) 0.2783(3) 0.0467(8) Uani 1 1 d . . . C24 C 0.3766(3) 0.5642(3) 0.1713(3) 0.0459(8) Uani 1 1 d . . . C25 C 0.3095(3) 0.4442(3) 0.1703(3) 0.0632(9) Uani 1 1 d . . . H25A H 0.2657 0.3816 0.0906 0.076 Uiso 1 1 calc R . . H25B H 0.3757 0.4185 0.2095 0.076 Uiso 1 1 calc R . . C26 C 0.2116(3) 0.4500(3) 0.2264(3) 0.0535(8) Uani 1 1 d . . . C27 C 0.1935(4) 0.3887(3) 0.2915(3) 0.0663(10) Uani 1 1 d . . . C28 C 0.2559(5) 0.3024(4) 0.3173(4) 0.1023(15) Uani 1 1 d . . . H28A H 0.3488 0.3419 0.3531 0.153 Uiso 1 1 calc R . . H28B H 0.2336 0.2304 0.2467 0.153 Uiso 1 1 calc R . . H28C H 0.2256 0.2790 0.3689 0.153 Uiso 1 1 calc R . . N29 N 0.1037(3) 0.4202(3) 0.3321(3) 0.0762(9) Uani 1 1 d . . . H29 H 0.0756 0.3943 0.3752 0.091 Uiso 1 1 calc R . . N30 N 0.0653(3) 0.4982(3) 0.2946(3) 0.0684(8) Uani 1 1 d . . . H30 H 0.0088 0.5309 0.3103 0.082 Uiso 1 1 calc R . . C31 C 0.1284(3) 0.5179(3) 0.2290(3) 0.0581(9) Uani 1 1 d . . . C32 C 0.1025(4) 0.6017(4) 0.1765(3) 0.0762(11) Uani 1 1 d . . . H32A H 0.0259 0.6195 0.1832 0.114 Uiso 1 1 calc R . . H32B H 0.0893 0.5629 0.0962 0.114 Uiso 1 1 calc R . . H32C H 0.1756 0.6768 0.2161 0.114 Uiso 1 1 calc R . . C33 C 0.2874(4) 0.4591(3) -0.0469(3) 0.0707(10) Uani 1 1 d . . . H33A H 0.2587 0.4847 -0.1062 0.106 Uiso 1 1 calc R . . H33B H 0.2131 0.4121 -0.0418 0.106 Uiso 1 1 calc R . . H33C H 0.3400 0.4094 -0.0657 0.106 Uiso 1 1 calc R . . C34 C 0.3668(3) 0.5711(3) 0.0678(2) 0.0456(8) Uani 1 1 d . . . C35 C 0.4304(3) 0.6811(3) 0.0705(3) 0.0486(8) Uani 1 1 d . . . C36 C 0.4360(3) 0.6855(3) -0.0398(3) 0.0595(9) Uani 1 1 d . . . H36A H 0.5251 0.7316 -0.0222 0.071 Uiso 1 1 calc R . . H36B H 0.4174 0.6020 -0.0958 0.071 Uiso 1 1 calc R . . C37 C 0.3479(3) 0.7398(3) -0.0980(3) 0.0504(8) Uani 1 1 d . . . C38 C 0.2461(3) 0.7766(3) -0.0781(3) 0.0563(9) Uani 1 1 d . . . C39 C 0.1850(4) 0.7782(5) 0.0068(4) 0.0926(14) Uani 1 1 d . . . H39A H 0.1186 0.8149 -0.0031 0.139 Uiso 1 1 calc R . . H39B H 0.2502 0.8252 0.0839 0.139 Uiso 1 1 calc R . . H39C H 0.1470 0.6955 -0.0058 0.139 Uiso 1 1 calc R . . N40 N 0.1981(3) 0.8156(3) -0.1566(2) 0.0629(8) Uani 1 1 d . . . H40 H 0.1339 0.8429 -0.1623 0.075 Uiso 1 1 calc R . . N41 N 0.2652(3) 0.8054(3) -0.2242(2) 0.0630(8) Uani 1 1 d . . . H41 H 0.2515 0.8254 -0.2803 0.076 Uiso 1 1 calc R . . C42 C 0.3574(3) 0.7590(3) -0.1913(3) 0.0566(9) Uani 1 1 d . . . C43 C 0.4488(4) 0.7357(5) -0.2501(4) 0.0933(14) Uani 1 1 d . . . H43A H 0.4349 0.6491 -0.2849 0.140 Uiso 1 1 calc R . . H43B H 0.5369 0.7792 -0.1945 0.140 Uiso 1 1 calc R . . H43C H 0.4339 0.7636 -0.3089 0.140 Uiso 1 1 calc R . . C44 C 0.5567(4) 0.9101(3) 0.1765(3) 0.0773(11) Uani 1 1 d . . . H44A H 0.5693 0.9770 0.2475 0.116 Uiso 1 1 calc R . . H44B H 0.4993 0.9157 0.1123 0.116 Uiso 1 1 calc R . . H44C H 0.6391 0.9140 0.1696 0.116 Uiso 1 1 calc R . . C45 C 0.4969(3) 0.7887(3) 0.1765(3) 0.0523(8) 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 O1 0.139(3) 0.100(2) 0.127(3) 0.036(2) 0.047(2) 0.064(2) N2 0.085(3) 0.107(3) 0.062(2) 0.025(2) 0.021(2) 0.049(2) O3 0.0860(19) 0.090(2) 0.0476(15) 0.0166(15) 0.0084(13) 0.0481(16) O4 0.164(4) 0.163(4) 0.076(2) 0.007(2) -0.018(2) 0.076(3) O5 0.0658(16) 0.0809(17) 0.0532(15) 0.0307(13) 0.0257(12) 0.0358(13) N6 0.065(2) 0.067(2) 0.058(2) 0.0281(17) 0.0207(17) 0.0271(17) O7 0.092(2) 0.146(3) 0.095(2) 0.047(2) 0.0426(18) 0.081(2) O8 0.099(2) 0.092(2) 0.0514(16) 0.0338(14) 0.0157(15) 0.0320(16) O9 0.095(2) 0.200(4) 0.155(3) 0.077(3) 0.081(3) 0.081(3) N10 0.076(3) 0.094(3) 0.094(3) 0.053(2) 0.045(2) 0.037(2) O11 0.085(2) 0.161(3) 0.104(2) 0.085(2) 0.051(2) 0.037(2) O12 0.089(2) 0.143(3) 0.078(2) 0.045(2) 0.0379(18) 0.0485(19) C13 0.073(3) 0.089(3) 0.054(2) 0.017(2) 0.0232(19) 0.038(2) C14 0.0468(19) 0.048(2) 0.049(2) 0.0184(16) 0.0116(17) 0.0154(16) N15 0.0411(16) 0.0603(18) 0.0575(18) 0.0241(15) 0.0127(14) 0.0192(13) N16 0.0533(18) 0.0637(18) 0.0420(16) 0.0208(14) 0.0069(13) 0.0182(14) C17 0.049(2) 0.056(2) 0.048(2) 0.0210(17) 0.0106(16) 0.0196(17) C18 0.088(3) 0.107(3) 0.054(2) 0.024(2) 0.024(2) 0.048(3) C19 0.0469(19) 0.0458(19) 0.0406(19) 0.0132(15) 0.0058(15) 0.0155(16) C20 0.059(2) 0.062(2) 0.052(2) 0.0195(18) 0.0094(17) 0.0292(18) C21 0.0383(18) 0.058(2) 0.0435(19) 0.0216(16) 0.0070(14) 0.0222(16) C22 0.058(2) 0.090(3) 0.052(2) 0.037(2) 0.0229(17) 0.029(2) C23 0.0421(18) 0.063(2) 0.0459(19) 0.0285(18) 0.0194(15) 0.0282(17) C24 0.0435(18) 0.054(2) 0.048(2) 0.0261(17) 0.0217(15) 0.0221(16) C25 0.077(2) 0.062(2) 0.065(2) 0.0313(19) 0.039(2) 0.029(2) C26 0.055(2) 0.050(2) 0.056(2) 0.0236(17) 0.0249(17) 0.0146(17) C27 0.062(2) 0.075(3) 0.075(3) 0.041(2) 0.038(2) 0.021(2) C28 0.131(4) 0.109(4) 0.138(4) 0.092(3) 0.084(3) 0.067(3) N29 0.073(2) 0.095(2) 0.086(2) 0.057(2) 0.0428(19) 0.0290(19) N30 0.0589(18) 0.090(2) 0.068(2) 0.0392(18) 0.0325(16) 0.0306(17) C31 0.052(2) 0.069(2) 0.047(2) 0.0238(18) 0.0166(17) 0.0153(19) C32 0.079(3) 0.104(3) 0.069(3) 0.049(2) 0.035(2) 0.047(2) C33 0.077(3) 0.071(2) 0.050(2) 0.0179(19) 0.0201(19) 0.021(2) C34 0.0445(18) 0.052(2) 0.0415(19) 0.0189(16) 0.0155(15) 0.0232(16) C35 0.0459(19) 0.066(2) 0.0430(19) 0.0306(18) 0.0155(15) 0.0271(17) C36 0.062(2) 0.082(3) 0.055(2) 0.0421(19) 0.0277(18) 0.0355(19) C37 0.050(2) 0.058(2) 0.0468(19) 0.0255(16) 0.0176(16) 0.0209(17) C38 0.055(2) 0.067(2) 0.0446(19) 0.0242(18) 0.0152(17) 0.0245(18) C39 0.095(3) 0.149(4) 0.074(3) 0.063(3) 0.048(2) 0.075(3) N40 0.0613(18) 0.083(2) 0.0548(18) 0.0369(16) 0.0202(16) 0.0371(16) N41 0.072(2) 0.076(2) 0.0622(19) 0.0453(16) 0.0295(17) 0.0346(17) C42 0.061(2) 0.070(2) 0.055(2) 0.0371(19) 0.0260(18) 0.0302(19) C43 0.101(3) 0.145(4) 0.102(3) 0.090(3) 0.066(3) 0.073(3) C44 0.073(3) 0.067(3) 0.079(3) 0.041(2) 0.010(2) 0.009(2) C45 0.0403(18) 0.061(2) 0.055(2) 0.0322(19) 0.0073(16) 0.0185(17) _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 N2 1.216(4) . ? N2 O4 1.225(4) . ? N2 O3 1.278(4) . ? O5 N6 1.271(3) . ? N6 O8 1.226(3) . ? N6 O7 1.226(3) . ? O9 N10 1.213(4) . ? N10 O12 1.227(4) . ? N10 O11 1.242(4) . ? C13 C14 1.476(5) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 N15 1.339(4) . ? C14 C19 1.398(4) . ? N15 N16 1.329(3) . ? N15 H15 0.8600 . ? N16 C17 1.337(4) . ? N16 H16 0.8600 . ? C17 C19 1.382(4) . ? C17 C18 1.489(5) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 C20 1.513(4) . ? C20 C21 1.524(4) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C23 1.398(4) . ? C21 C45 1.402(4) . ? C22 C23 1.515(4) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 C24 1.412(4) . ? C24 C34 1.400(4) . ? C24 C25 1.522(4) . ? C25 C26 1.508(4) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 C27 1.381(5) . ? C26 C31 1.387(4) . ? C27 N29 1.345(4) . ? C27 C28 1.486(5) . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? N29 N30 1.335(4) . ? N29 H29 0.8600 . ? N30 C31 1.339(4) . ? N30 H30 0.8600 . ? C31 C32 1.485(5) . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C33 C34 1.511(4) . ? C33 H33A 0.9600 . ? C33 H33B 0.9600 . ? C33 H33C 0.9600 . ? C34 C35 1.392(4) . ? C35 C45 1.412(4) . ? C35 C36 1.522(4) . ? C36 C37 1.512(4) . ? C36 H36A 0.9700 . ? C36 H36B 0.9700 . ? C37 C38 1.384(4) . ? C37 C42 1.387(4) . ? C38 N40 1.342(4) . ? C38 C39 1.489(5) . ? C39 H39A 0.9600 . ? C39 H39B 0.9600 . ? C39 H39C 0.9600 . ? N40 N41 1.329(4) . ? N40 H40 0.8600 . ? N41 C42 1.339(4) . ? N41 H41 0.8600 . ? C42 C43 1.485(5) . ? C43 H43A 0.9600 . ? C43 H43B 0.9600 . ? C43 H43C 0.9600 . ? C44 C45 1.521(4) . ? C44 H44A 0.9600 . ? C44 H44B 0.9600 . ? C44 H44C 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 O1 N2 O4 123.3(4) . . ? O1 N2 O3 118.8(4) . . ? O4 N2 O3 117.9(4) . . ? O8 N6 O7 123.2(3) . . ? O8 N6 O5 118.5(3) . . ? O7 N6 O5 118.3(3) . . ? O9 N10 O12 122.0(4) . . ? O9 N10 O11 120.5(4) . . ? O12 N10 O11 117.5(4) . . ? C14 C13 H13A 109.5 . . ? C14 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C14 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N15 C14 C19 106.8(3) . . ? N15 C14 C13 121.0(3) . . ? C19 C14 C13 132.2(3) . . ? N16 N15 C14 110.1(3) . . ? N16 N15 H15 125.0 . . ? C14 N15 H15 125.0 . . ? N15 N16 C17 108.9(3) . . ? N15 N16 H16 125.5 . . ? C17 N16 H16 125.5 . . ? N16 C17 C19 108.1(3) . . ? N16 C17 C18 120.9(3) . . ? C19 C17 C18 131.1(3) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 C14 106.1(3) . . ? C17 C19 C20 124.8(3) . . ? C14 C19 C20 129.0(3) . . ? C19 C20 C21 115.5(3) . . ? C19 C20 H20A 108.4 . . ? C21 C20 H20A 108.4 . . ? C19 C20 H20B 108.4 . . ? C21 C20 H20B 108.4 . . ? H20A C20 H20B 107.5 . . ? C23 C21 C45 120.3(3) . . ? C23 C21 C20 118.7(3) . . ? C45 C21 C20 121.0(3) . . ? C23 C22 H22A 109.5 . . ? C23 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C23 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21 C23 C24 119.9(3) . . ? C21 C23 C22 120.1(3) . . ? C24 C23 C22 120.0(3) . . ? C34 C24 C23 119.8(3) . . ? C34 C24 C25 120.8(3) . . ? C23 C24 C25 119.4(3) . . ? C26 C25 C24 115.1(3) . . ? C26 C25 H25A 108.5 . . ? C24 C25 H25A 108.5 . . ? C26 C25 H25B 108.5 . . ? C24 C25 H25B 108.5 . . ? H25A C25 H25B 107.5 . . ? C27 C26 C31 106.7(3) . . ? C27 C26 C25 124.2(3) . . ? C31 C26 C25 129.1(3) . . ? N29 C27 C26 107.5(3) . . ? N29 C27 C28 122.6(3) . . ? C26 C27 C28 130.0(3) . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? N30 N29 C27 109.0(3) . . ? N30 N29 H29 125.5 . . ? C27 N29 H29 125.5 . . ? N29 N30 C31 109.5(3) . . ? N29 N30 H30 125.2 . . ? C31 N30 H30 125.2 . . ? N30 C31 C26 107.3(3) . . ? N30 C31 C32 120.0(3) . . ? C26 C31 C32 132.7(3) . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C34 C33 H33A 109.5 . . ? C34 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C34 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C35 C34 C24 120.0(3) . . ? C35 C34 C33 119.9(3) . . ? C24 C34 C33 120.1(3) . . ? C34 C35 C45 120.4(3) . . ? C34 C35 C36 120.5(3) . . ? C45 C35 C36 119.0(3) . . ? C37 C36 C35 118.9(3) . . ? C37 C36 H36A 107.6 . . ? C35 C36 H36A 107.6 . . ? C37 C36 H36B 107.6 . . ? C35 C36 H36B 107.6 . . ? H36A C36 H36B 107.0 . . ? C38 C37 C42 106.2(3) . . ? C38 C37 C36 131.7(3) . . ? C42 C37 C36 122.1(3) . . ? N40 C38 C37 107.5(3) . . ? N40 C38 C39 119.1(3) . . ? C37 C38 C39 133.4(3) . . ? C38 C39 H39A 109.5 . . ? C38 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? C38 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? N41 N40 C38 109.4(3) . . ? N41 N40 H40 125.3 . . ? C38 N40 H40 125.3 . . ? N40 N41 C42 109.2(3) . . ? N40 N41 H41 125.4 . . ? C42 N41 H41 125.4 . . ? N41 C42 C37 107.7(3) . . ? N41 C42 C43 122.6(3) . . ? C37 C42 C43 129.7(3) . . ? C42 C43 H43A 109.5 . . ? C42 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? C42 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? C45 C44 H44A 109.5 . . ? C45 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? C45 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? C21 C45 C35 119.2(3) . . ? C21 C45 C44 121.2(3) . . ? C35 C45 C44 119.5(3) . . ? 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 N15 H15 O5 0.86 2.02 2.803(4) 151.4 1_655 N15 H15 O8 0.86 2.38 3.158(4) 150.7 1_655 N15 H15 N6 0.86 2.56 3.415(4) 175.8 1_655 N16 H16 O3 0.86 1.91 2.736(4) 161.7 1_665 N16 H16 N2 0.86 2.65 3.504(5) 171.4 1_665 N29 H29 O11 0.86 1.92 2.733(4) 158.0 2_666 N29 H29 N10 0.86 2.67 3.354(6) 138.0 2_666 N30 H30 O12 0.86 1.92 2.730(4) 157.0 1_455 N30 H30 O11 0.86 2.58 3.235(4) 134.2 1_455 N30 H30 N10 0.86 2.62 3.413(5) 154.5 1_455 N40 H40 O3 0.86 1.94 2.731(4) 151.4 1_564 N41 H41 O5 0.86 1.93 2.745(4) 156.8 1_554 N41 H41 O7 0.86 2.54 3.278(5) 144.1 1_554 N41 H41 N6 0.86 2.58 3.416(5) 163.1 1_554 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 22.72 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.237 _refine_diff_density_min -0.212 _refine_diff_density_rms 0.039 # Attachment 'Complex-3.cif' data_Complex-3 _database_code_depnum_ccdc_archive 'CCDC 747561' #TrackingRef 'Complex-3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H29 N9 O10' _chemical_formula_weight 567.53 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 10.5136(8) _cell_length_b 10.8271(8) _cell_length_c 11.7809(8) _cell_angle_alpha 91.090(2) _cell_angle_beta 93.523(2) _cell_angle_gamma 106.4840(10) _cell_volume 1282.56(16) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6168 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 31.27 _exptl_crystal_description Block _exptl_crystal_colour 'Pale yellow' _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.470 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 596 _exptl_absorpt_coefficient_mu 0.119 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9409 _exptl_absorpt_correction_T_max 0.9767 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _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 'CCD area detector' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean 3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12157 _diffrn_reflns_av_R_equivalents 0.0203 _diffrn_reflns_av_sigmaI/netI 0.0239 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4502 _reflns_number_gt 3906 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'MERCURY 2.2' _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^)+(0.0703P)^2^+1.1412P] 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 4502 _refine_ls_number_parameters 376 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0533 _refine_ls_R_factor_gt 0.0468 _refine_ls_wR_factor_ref 0.1338 _refine_ls_wR_factor_gt 0.1270 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _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 O1A O 0.86414(17) -0.02078(18) 0.25978(14) 0.0391(5) Uani 0.916(3) 1 d P . . O1B O 0.8593(19) 0.106(2) 0.2064(16) 0.0391(5) Uani 0.084(3) 1 d P . . O2 O 0.6027(2) 0.6801(3) 0.4158(2) 0.0875(9) Uani 1 1 d . . . N3 N 0.52442(16) 0.65478(16) 0.33217(15) 0.0269(4) Uani 1 1 d . . . O4 O 0.4410(2) 0.7139(2) 0.32127(16) 0.0663(7) Uani 1 1 d . . . O5 O 0.52940(16) 0.57107(15) 0.26081(13) 0.0365(4) Uani 1 1 d . . . O6 O 0.02733(16) 0.82992(15) 0.17146(12) 0.0362(4) Uani 1 1 d . . . N7 N 0.02254(18) 0.80637(16) 0.06611(15) 0.0290(4) Uani 1 1 d . . . O8 O 0.09407(18) 0.88678(15) 0.00433(14) 0.0423(4) Uani 1 1 d . . . O9 O -0.0507(2) 0.70500(16) 0.02257(15) 0.0557(6) Uani 1 1 d . . . O10 O 0.39697(18) 0.11055(19) 0.86773(16) 0.0495(5) Uani 1 1 d . . . N11 N 0.45981(19) 0.03096(19) 0.84816(15) 0.0352(4) Uani 1 1 d . . . O12 O 0.57851(16) 0.05389(16) 0.88905(13) 0.0373(4) Uani 1 1 d . . . O13 O 0.40788(18) -0.06833(17) 0.78838(14) 0.0458(4) Uani 1 1 d . . . N14 N 0.6401(2) -0.06281(18) 0.48801(17) 0.0382(5) Uani 1 1 d . . . H14 H 0.6062 -0.1252 0.4390 0.046 Uiso 1 1 calc R . . C15 C 0.6193(2) -0.0650(2) 0.6000(2) 0.0348(5) Uani 1 1 d . . . H15 H 0.5669 -0.1336 0.6378 0.042 Uiso 1 1 calc R . . C16 C 0.6882(2) 0.0503(2) 0.64627(19) 0.0360(5) Uani 1 1 d . . . H16 H 0.6926 0.0768 0.7223 0.043 Uiso 1 1 calc R . . N17 N 0.75134(16) 0.12185(15) 0.56028(13) 0.0213(4) Uani 1 1 d . . . C18 C 0.7209(3) 0.0505(2) 0.4657(2) 0.0383(6) Uani 1 1 d . . . H18 H 0.7512 0.0756 0.3948 0.046 Uiso 1 1 calc R . . C19 C 0.83693(19) 0.25577(18) 0.57665(16) 0.0221(4) Uani 1 1 d . . . H19A H 0.9080 0.2583 0.6340 0.027 Uiso 1 1 calc R . . H19B H 0.7848 0.3091 0.6050 0.027 Uiso 1 1 calc R . . C20 C 0.89717(18) 0.31194(18) 0.46909(15) 0.0197(4) Uani 1 1 d . . . C21 C 0.83104(18) 0.37910(17) 0.39793(15) 0.0192(4) Uani 1 1 d . . . C22 C 0.69013(19) 0.3799(2) 0.41625(17) 0.0249(4) Uani 1 1 d . . . H22C H 0.6539 0.3178 0.4714 0.037 Uiso 1 1 calc R . . H22A H 0.6369 0.3584 0.3456 0.037 Uiso 1 1 calc R . . H22B H 0.6902 0.4641 0.4434 0.037 Uiso 1 1 calc R . . C23 C 0.89560(19) 0.44370(17) 0.30576(15) 0.0200(4) Uani 1 1 d . . . C24 C 0.8250(2) 0.51900(19) 0.23137(16) 0.0242(4) Uani 1 1 d . . . H24B H 0.7632 0.5478 0.2755 0.029 Uiso 1 1 calc R . . H24A H 0.8896 0.5948 0.2061 0.029 Uiso 1 1 calc R . . N25 N 0.75158(16) 0.44059(16) 0.13060(13) 0.0239(4) Uani 1 1 d . . . C26 C 0.6753(2) 0.4849(2) 0.05053(17) 0.0285(5) Uani 1 1 d . . . H26 H 0.6632 0.5667 0.0498 0.034 Uiso 1 1 calc R . . C27 C 0.6218(2) 0.3874(2) -0.02630(18) 0.0306(5) Uani 1 1 d . . . H27 H 0.5655 0.3893 -0.0899 0.037 Uiso 1 1 calc R . . N28 N 0.66568(18) 0.28517(19) 0.00667(15) 0.0303(4) Uani 1 1 d . . . H28 H 0.637(3) 0.201(3) -0.031(2) 0.048(8) Uiso 1 1 d . . . C29 C 0.7440(2) 0.3195(2) 0.10164(17) 0.0284(5) Uani 1 1 d . . . H29 H 0.7864 0.2673 0.1413 0.034 Uiso 1 1 calc R . . C30 C 1.0930(2) 0.5079(2) 0.18422(17) 0.0283(5) Uani 1 1 d . . . H30C H 1.0294 0.5302 0.1327 0.042 Uiso 1 1 calc R . . H30A H 1.1338 0.4519 0.1453 0.042 Uiso 1 1 calc R . . H30B H 1.1601 0.5848 0.2114 0.042 Uiso 1 1 calc R . . C31 C 1.02340(19) 0.43961(18) 0.28400(16) 0.0210(4) Uani 1 1 d . . . C32 C 1.08642(18) 0.36853(18) 0.35442(16) 0.0219(4) Uani 1 1 d . . . C33 C 1.2278(2) 0.3704(2) 0.33497(18) 0.0282(5) Uani 1 1 d . . . H33B H 1.2775 0.4572 0.3176 0.034 Uiso 1 1 calc R . . H33A H 1.2686 0.3480 0.4047 0.034 Uiso 1 1 calc R . . N34 N 1.23744(16) 0.28070(16) 0.24171(14) 0.0244(4) Uani 1 1 d . . . C35 C 1.3503(2) 0.2948(2) 0.18249(18) 0.0278(5) Uani 1 1 d . . . H35 H 1.4282 0.3625 0.1910 0.033 Uiso 1 1 calc R . . C36 C 1.3253(2) 0.1912(2) 0.11007(19) 0.0302(5) Uani 1 1 d . . . H36 H 1.3827 0.1741 0.0590 0.036 Uiso 1 1 calc R . . N37 N 1.19977(18) 0.11626(18) 0.12603(15) 0.0297(4) Uani 1 1 d . . . H37 H 1.160(3) 0.036(3) 0.088(2) 0.051(8) Uiso 1 1 d . . . C38 C 1.1480(2) 0.1715(2) 0.20497(18) 0.0280(5) Uani 1 1 d . . . H38 H 1.0634 0.1395 0.2305 0.034 Uiso 1 1 calc R . . C39 C 1.0851(2) 0.2147(2) 0.51456(19) 0.0316(5) Uani 1 1 d . . . H39B H 1.1380 0.1788 0.4674 0.047 Uiso 1 1 calc R . . H39C H 1.0166 0.1463 0.5436 0.047 Uiso 1 1 calc R . . H39A H 1.1406 0.2643 0.5769 0.047 Uiso 1 1 calc R . . C40 C 1.02245(19) 0.30102(18) 0.44490(16) 0.0217(4) 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 O1A 0.0377(10) 0.0489(11) 0.0297(9) -0.0040(8) 0.0038(7) 0.0111(8) O1B 0.0377(10) 0.0489(11) 0.0297(9) -0.0040(8) 0.0038(7) 0.0111(8) O2 0.0644(14) 0.1062(19) 0.0983(18) -0.0767(16) -0.0563(13) 0.0525(14) N3 0.0216(8) 0.0225(9) 0.0365(10) 0.0008(7) 0.0041(7) 0.0058(7) O4 0.0853(15) 0.1074(17) 0.0455(11) 0.0342(11) 0.0331(10) 0.0829(14) O5 0.0457(9) 0.0333(9) 0.0313(8) -0.0063(7) -0.0061(7) 0.0151(7) O6 0.0472(10) 0.0373(9) 0.0225(8) -0.0010(6) -0.0008(7) 0.0103(7) N7 0.0380(10) 0.0226(9) 0.0256(9) 0.0028(7) -0.0025(8) 0.0082(8) O8 0.0539(10) 0.0326(9) 0.0338(9) 0.0005(7) 0.0112(8) 0.0001(8) O9 0.0857(14) 0.0280(9) 0.0342(9) 0.0023(7) -0.0156(9) -0.0108(9) O10 0.0426(10) 0.0627(12) 0.0467(11) -0.0098(9) 0.0106(8) 0.0199(9) N11 0.0393(11) 0.0405(11) 0.0231(9) 0.0032(8) 0.0061(8) 0.0059(9) O12 0.0427(10) 0.0405(9) 0.0280(8) -0.0018(7) -0.0006(7) 0.0118(7) O13 0.0518(11) 0.0441(10) 0.0345(9) -0.0068(8) -0.0005(8) 0.0036(8) N14 0.0462(11) 0.0221(9) 0.0429(12) -0.0060(8) 0.0098(9) 0.0034(8) C15 0.0299(11) 0.0346(12) 0.0382(13) 0.0143(10) 0.0047(9) 0.0054(9) C16 0.0360(12) 0.0416(13) 0.0239(11) 0.0102(9) 0.0048(9) -0.0006(10) N17 0.0224(8) 0.0234(8) 0.0201(8) 0.0032(6) 0.0038(6) 0.0092(7) C18 0.0557(15) 0.0266(11) 0.0285(12) -0.0029(9) 0.0157(11) 0.0029(10) C19 0.0243(10) 0.0233(10) 0.0184(9) -0.0005(8) 0.0020(8) 0.0062(8) C20 0.0216(9) 0.0198(9) 0.0163(9) -0.0015(7) 0.0011(7) 0.0041(7) C21 0.0200(9) 0.0183(9) 0.0187(9) -0.0026(7) 0.0018(7) 0.0047(7) C22 0.0234(10) 0.0302(11) 0.0236(10) 0.0036(8) 0.0038(8) 0.0110(8) C23 0.0247(10) 0.0180(9) 0.0165(9) -0.0016(7) 0.0013(7) 0.0048(8) C24 0.0308(10) 0.0229(10) 0.0197(10) 0.0016(8) 0.0032(8) 0.0088(8) N25 0.0252(9) 0.0287(9) 0.0191(8) 0.0047(7) 0.0038(7) 0.0090(7) C26 0.0279(10) 0.0374(12) 0.0244(10) 0.0101(9) 0.0047(8) 0.0150(9) C27 0.0255(11) 0.0464(13) 0.0210(10) 0.0069(9) 0.0031(8) 0.0113(9) N28 0.0305(9) 0.0360(11) 0.0232(9) -0.0014(8) 0.0007(7) 0.0078(8) C29 0.0320(11) 0.0292(11) 0.0241(10) 0.0011(8) -0.0013(9) 0.0096(9) C30 0.0307(11) 0.0280(11) 0.0246(10) -0.0006(8) 0.0100(9) 0.0042(9) C31 0.0241(10) 0.0191(9) 0.0179(9) -0.0029(7) 0.0038(7) 0.0028(8) C32 0.0192(9) 0.0247(10) 0.0202(10) -0.0059(8) 0.0014(7) 0.0043(8) C33 0.0219(10) 0.0355(12) 0.0263(11) -0.0078(9) 0.0023(8) 0.0073(9) N34 0.0213(8) 0.0275(9) 0.0257(9) -0.0002(7) 0.0053(7) 0.0082(7) C35 0.0232(10) 0.0279(11) 0.0332(11) 0.0023(9) 0.0091(9) 0.0073(8) C36 0.0314(11) 0.0287(11) 0.0331(12) 0.0008(9) 0.0119(9) 0.0110(9) N37 0.0338(10) 0.0243(9) 0.0303(10) -0.0025(8) 0.0068(8) 0.0065(8) C38 0.0250(10) 0.0298(11) 0.0275(11) -0.0013(9) 0.0043(8) 0.0049(8) C39 0.0290(11) 0.0407(13) 0.0295(11) 0.0042(9) 0.0001(9) 0.0172(10) C40 0.0213(9) 0.0242(10) 0.0195(9) -0.0031(8) -0.0019(7) 0.0073(8) _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 O1B 1.53(2) . ? O2 N3 1.218(3) . ? N3 O4 1.226(2) . ? N3 O5 1.239(2) . ? O6 N7 1.257(2) . ? N7 O9 1.229(2) . ? N7 O8 1.254(2) . ? O10 N11 1.252(3) . ? N11 O13 1.241(3) . ? N11 O12 1.264(2) . ? N14 C18 1.321(3) . ? N14 C15 1.350(3) . ? N14 H14 0.8600 . ? C15 C16 1.338(3) . ? C15 H15 0.9300 . ? C16 N17 1.374(3) . ? C16 H16 0.9300 . ? N17 C18 1.313(3) . ? N17 C19 1.475(2) . ? C18 H18 0.9300 . ? C19 C20 1.512(3) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.398(3) . ? C20 C40 1.401(3) . ? C21 C23 1.407(3) . ? C21 C22 1.513(3) . ? C22 H22C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C23 C31 1.396(3) . ? C23 C24 1.508(3) . ? C24 N25 1.484(3) . ? C24 H24B 0.9700 . ? C24 H24A 0.9700 . ? N25 C29 1.327(3) . ? N25 C26 1.381(3) . ? C26 C27 1.347(3) . ? C26 H26 0.9300 . ? C27 N28 1.369(3) . ? C27 H27 0.9300 . ? N28 C29 1.328(3) . ? N28 H28 0.97(3) . ? C29 H29 0.9300 . ? C30 C31 1.515(3) . ? C30 H30C 0.9600 . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C31 C32 1.402(3) . ? C32 C40 1.401(3) . ? C32 C33 1.512(3) . ? C33 N34 1.480(3) . ? C33 H33B 0.9700 . ? C33 H33A 0.9700 . ? N34 C38 1.330(3) . ? N34 C35 1.386(3) . ? C35 C36 1.350(3) . ? C35 H35 0.9300 . ? C36 N37 1.365(3) . ? C36 H36 0.9300 . ? N37 C38 1.321(3) . ? N37 H37 0.94(3) . ? C38 H38 0.9300 . ? C39 C40 1.514(3) . ? C39 H39B 0.9600 . ? C39 H39C 0.9600 . ? C39 H39A 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 O2 N3 O4 118.2(2) . . ? O2 N3 O5 120.47(18) . . ? O4 N3 O5 121.4(2) . . ? O9 N7 O8 119.29(18) . . ? O9 N7 O6 120.96(18) . . ? O8 N7 O6 119.75(17) . . ? O13 N11 O10 121.0(2) . . ? O13 N11 O12 120.0(2) . . ? O10 N11 O12 118.94(19) . . ? C18 N14 C15 109.07(19) . . ? C18 N14 H14 125.5 . . ? C15 N14 H14 125.5 . . ? C16 C15 N14 107.11(19) . . ? C16 C15 H15 126.4 . . ? N14 C15 H15 126.4 . . ? C15 C16 N17 107.1(2) . . ? C15 C16 H16 126.5 . . ? N17 C16 H16 126.5 . . ? C18 N17 C16 108.10(18) . . ? C18 N17 C19 128.09(17) . . ? C16 N17 C19 123.81(17) . . ? N17 C18 N14 108.6(2) . . ? N17 C18 H18 125.7 . . ? N14 C18 H18 125.7 . . ? N17 C19 C20 113.42(15) . . ? N17 C19 H19A 108.9 . . ? C20 C19 H19A 108.9 . . ? N17 C19 H19B 108.9 . . ? C20 C19 H19B 108.9 . . ? H19A C19 H19B 107.7 . . ? C21 C20 C40 120.71(17) . . ? C21 C20 C19 120.08(17) . . ? C40 C20 C19 119.14(17) . . ? C20 C21 C23 119.22(17) . . ? C20 C21 C22 121.13(17) . . ? C23 C21 C22 119.62(17) . . ? C21 C22 H22C 109.5 . . ? C21 C22 H22A 109.5 . . ? H22C C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22C C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C31 C23 C21 120.74(17) . . ? C31 C23 C24 120.38(17) . . ? C21 C23 C24 118.87(17) . . ? N25 C24 C23 111.76(15) . . ? N25 C24 H24B 109.3 . . ? C23 C24 H24B 109.3 . . ? N25 C24 H24A 109.3 . . ? C23 C24 H24A 109.3 . . ? H24B C24 H24A 107.9 . . ? C29 N25 C26 108.21(17) . . ? C29 N25 C24 128.13(17) . . ? C26 N25 C24 123.66(17) . . ? C27 C26 N25 107.08(19) . . ? C27 C26 H26 126.5 . . ? N25 C26 H26 126.5 . . ? C26 C27 N28 107.28(18) . . ? C26 C27 H27 126.4 . . ? N28 C27 H27 126.4 . . ? C29 N28 C27 108.64(19) . . ? C29 N28 H28 127.3(17) . . ? C27 N28 H28 123.9(17) . . ? N25 C29 N28 108.80(19) . . ? N25 C29 H29 125.6 . . ? N28 C29 H29 125.6 . . ? C31 C30 H30C 109.5 . . ? C31 C30 H30A 109.5 . . ? H30C C30 H30A 109.5 . . ? C31 C30 H30B 109.5 . . ? H30C C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C23 C31 C32 119.12(17) . . ? C23 C31 C30 121.05(18) . . ? C32 C31 C30 119.82(17) . . ? C40 C32 C31 120.95(17) . . ? C40 C32 C33 119.93(18) . . ? C31 C32 C33 119.06(17) . . ? N34 C33 C32 113.45(16) . . ? N34 C33 H33B 108.9 . . ? C32 C33 H33B 108.9 . . ? N34 C33 H33A 108.9 . . ? C32 C33 H33A 108.9 . . ? H33B C33 H33A 107.7 . . ? C38 N34 C35 108.29(17) . . ? C38 N34 C33 127.92(17) . . ? C35 N34 C33 123.65(17) . . ? C36 C35 N34 106.77(18) . . ? C36 C35 H35 126.6 . . ? N34 C35 H35 126.6 . . ? C35 C36 N37 107.05(18) . . ? C35 C36 H36 126.5 . . ? N37 C36 H36 126.5 . . ? C38 N37 C36 109.44(18) . . ? C38 N37 H37 126.7(18) . . ? C36 N37 H37 123.8(18) . . ? N37 C38 N34 108.46(18) . . ? N37 C38 H38 125.8 . . ? N34 C38 H38 125.8 . . ? C40 C39 H39B 109.5 . . ? C40 C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? C40 C39 H39A 109.5 . . ? H39B C39 H39A 109.5 . . ? H39C C39 H39A 109.5 . . ? C32 C40 C20 119.03(17) . . ? C32 C40 C39 121.05(17) . . ? C20 C40 C39 119.91(17) . . ? 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 N14 H14 O2 0.86 2.11 2.806(3) 137.7 1_545 N28 H28 O12 0.97(3) 1.76(3) 2.728(2) 175(3) 1_554 N37 H37 O8 0.94(3) 1.82(3) 2.751(2) 175(3) 1_645 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.622 _refine_diff_density_min -0.425 _refine_diff_density_rms 0.054 # Attachment 'Complex-6.cif' data_Complex-6 _database_code_depnum_ccdc_archive 'CCDC 747562' #TrackingRef 'Complex-6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H44 Cl3 N6 O2.50' _chemical_formula_weight 599.03 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 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 26.309(4) _cell_length_b 9.8633(14) _cell_length_c 25.970(3) _cell_angle_alpha 90.00 _cell_angle_beta 112.137(2) _cell_angle_gamma 90.00 _cell_volume 6242.4(15) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3002 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 21.13 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.275 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2552 _exptl_absorpt_coefficient_mu 0.329 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9134 _exptl_absorpt_correction_T_max 0.9553 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _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 'CCD area detector' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean 3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20603 _diffrn_reflns_av_R_equivalents 0.0623 _diffrn_reflns_av_sigmaI/netI 0.0406 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 21.42 _reflns_number_total 3549 _reflns_number_gt 2844 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'MERCURY 2.2' _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. The hydrogen atoms of water molecules labeled O1 and O2 were located from the difference Fourier map and refined isotropically, the OH distances involving the water molecules were refined with a DFIX restraint of 0.88 ang. ; _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^)+(0.0440P)^2^+7.3625P] 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 3549 _refine_ls_number_parameters 373 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0493 _refine_ls_R_factor_gt 0.0362 _refine_ls_wR_factor_ref 0.0939 _refine_ls_wR_factor_gt 0.0875 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.043 _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 O1 O 0.60560(9) 0.6460(2) 0.30260(9) 0.0282(6) Uani 1 1 d D . . H1A H 0.6257(15) 0.600(4) 0.3324(12) 0.069(14) Uiso 1 1 d D . . H1B H 0.5876(18) 0.705(4) 0.3149(19) 0.104(19) Uiso 1 1 d D . . O2 O 0.27451(10) 0.4488(3) 0.70108(10) 0.0327(6) Uani 1 1 d D . . H2A H 0.2466(12) 0.394(3) 0.6873(15) 0.061(14) Uiso 1 1 d D . . H2B H 0.282(2) 0.479(5) 0.6730(15) 0.11(2) Uiso 1 1 d D . . O3 O 0.5000 0.0401(3) 0.2500 0.0366(8) Uani 1 2 d S . . Cl4 Cl 0.31184(3) 0.47937(8) 0.10046(3) 0.0251(2) Uani 1 1 d . . . Cl5 Cl 0.18381(3) 0.77612(8) 0.15164(3) 0.0294(2) Uani 1 1 d . . . Cl6 Cl 0.46539(3) 0.82332(8) 0.15226(3) 0.0263(2) Uani 1 1 d . . . C7 C 0.40631(12) 0.1618(3) 0.12400(12) 0.0214(8) Uani 1 1 d . . . H7A H 0.4402 0.1833 0.1539 0.032 Uiso 1 1 calc R . . H7B H 0.3927 0.0767 0.1314 0.032 Uiso 1 1 calc R . . H7C H 0.3799 0.2318 0.1208 0.032 Uiso 1 1 calc R . . C8 C 0.41584(12) 0.1520(3) 0.07004(12) 0.0167(7) Uani 1 1 d . . . C9 C 0.46821(12) 0.1710(3) 0.06914(12) 0.0175(7) Uani 1 1 d . . . C10 C 0.51660(12) 0.1888(3) 0.12441(12) 0.0206(8) Uani 1 1 d . . . H10A H 0.5140 0.1198 0.1499 0.025 Uiso 1 1 calc R . . H10B H 0.5502 0.1721 0.1182 0.025 Uiso 1 1 calc R . . C11 C 0.52156(12) 0.3253(3) 0.15236(12) 0.0183(7) Uani 1 1 d . . . C12 C 0.49270(12) 0.4458(3) 0.13344(12) 0.0193(8) Uani 1 1 d . . . C13 C 0.44746(12) 0.4846(3) 0.08067(12) 0.0244(8) Uani 1 1 d . . . H13A H 0.4135 0.4475 0.0801 0.037 Uiso 1 1 calc R . . H13B H 0.4549 0.4497 0.0497 0.037 Uiso 1 1 calc R . . H13C H 0.4447 0.5816 0.0781 0.037 Uiso 1 1 calc R . . N14 N 0.51230(10) 0.5383(3) 0.17389(10) 0.0213(6) Uani 1 1 d . . . H14 H 0.5011 0.6207 0.1720 0.026 Uiso 1 1 calc R . . N15 N 0.55194(10) 0.4828(3) 0.21758(10) 0.0210(6) Uani 1 1 d . . . H15 H 0.5701 0.5236 0.2483 0.025 Uiso 1 1 calc R . . C16 C 0.55904(12) 0.3533(3) 0.20601(12) 0.0191(7) Uani 1 1 d . . . C17 C 0.60103(12) 0.2648(3) 0.24643(12) 0.0247(8) Uani 1 1 d . . . H17A H 0.6193 0.3138 0.2803 0.037 Uiso 1 1 calc R . . H17B H 0.6274 0.2372 0.2311 0.037 Uiso 1 1 calc R . . H17C H 0.5835 0.1861 0.2540 0.037 Uiso 1 1 calc R . . C18 C 0.53041(12) 0.2027(3) 0.01505(13) 0.0238(8) Uani 1 1 d . . . H18A H 0.5437 0.1236 0.0026 0.036 Uiso 1 1 calc R . . H18B H 0.5560 0.2283 0.0512 0.036 Uiso 1 1 calc R . . H18C H 0.5264 0.2757 -0.0106 0.036 Uiso 1 1 calc R . . C19 C 0.47508(12) 0.1717(3) 0.01828(12) 0.0164(7) Uani 1 1 d . . . C20 C 0.43015(12) 0.1437(3) -0.03116(12) 0.0165(7) Uani 1 1 d . . . C21 C 0.43640(12) 0.1418(3) -0.08705(12) 0.0217(8) Uani 1 1 d . . . H21A H 0.4747 0.1562 -0.0809 0.026 Uiso 1 1 calc R . . H21B H 0.4262 0.0527 -0.1035 0.026 Uiso 1 1 calc R . . C22 C 0.40237(12) 0.2467(3) -0.12779(12) 0.0189(7) Uani 1 1 d . . . C23 C 0.39226(12) 0.3799(3) -0.11652(13) 0.0204(8) Uani 1 1 d . . . C24 C 0.41014(13) 0.4590(3) -0.06413(13) 0.0279(8) Uani 1 1 d . . . H24A H 0.3964 0.5500 -0.0720 0.042 Uiso 1 1 calc R . . H24B H 0.4495 0.4608 -0.0477 0.042 Uiso 1 1 calc R . . H24C H 0.3961 0.4174 -0.0388 0.042 Uiso 1 1 calc R . . N25 N 0.35881(10) 0.4368(3) -0.16439(10) 0.0226(6) Uani 1 1 d . . . H25 H 0.3465 0.5184 -0.1681 0.027 Uiso 1 1 calc R . . N26 N 0.34779(10) 0.3454(3) -0.20551(10) 0.0236(7) Uani 1 1 d . . . H26 H 0.3274 0.3594 -0.2398 0.028 Uiso 1 1 calc R . . C27 C 0.37375(12) 0.2284(3) -0.18465(13) 0.0222(8) Uani 1 1 d . . . C28 C 0.36917(15) 0.1079(3) -0.22039(13) 0.0325(9) Uani 1 1 d . . . H28A H 0.3443 0.1272 -0.2576 0.049 Uiso 1 1 calc R . . H28B H 0.3556 0.0323 -0.2060 0.049 Uiso 1 1 calc R . . H28C H 0.4046 0.0861 -0.2207 0.049 Uiso 1 1 calc R . . C29 C 0.33245(12) 0.0707(3) -0.08224(12) 0.0221(8) Uani 1 1 d . . . H29A H 0.3038 0.0304 -0.0729 0.033 Uiso 1 1 calc R . . H29B H 0.3461 0.0055 -0.1013 0.033 Uiso 1 1 calc R . . H29C H 0.3181 0.1477 -0.1059 0.033 Uiso 1 1 calc R . . C30 C 0.37858(12) 0.1158(3) -0.02968(12) 0.0171(7) Uani 1 1 d . . . C31 C 0.37068(12) 0.1264(3) 0.02053(12) 0.0165(7) Uani 1 1 d . . . C32 C 0.31358(12) 0.1179(3) 0.02239(13) 0.0199(7) Uani 1 1 d . . . H32A H 0.3085 0.1966 0.0424 0.024 Uiso 1 1 calc R . . H32B H 0.2870 0.1245 -0.0154 0.024 Uiso 1 1 calc R . . C33 C 0.30027(11) -0.0064(3) 0.04850(12) 0.0176(7) Uani 1 1 d . . . C34 C 0.26900(12) -0.0056(3) 0.08112(13) 0.0236(8) Uani 1 1 d . . . C35 C 0.24285(15) 0.1089(3) 0.09916(15) 0.0376(9) Uani 1 1 d . . . H35A H 0.2099 0.1354 0.0690 0.056 Uiso 1 1 calc R . . H35B H 0.2677 0.1843 0.1098 0.056 Uiso 1 1 calc R . . H35C H 0.2341 0.0810 0.1302 0.056 Uiso 1 1 calc R . . N36 N 0.26419(10) -0.1347(3) 0.09574(11) 0.0258(7) Uani 1 1 d . . . H36 H 0.2469 -0.1604 0.1163 0.031 Uiso 1 1 calc R . . N37 N 0.29067(10) -0.2167(3) 0.07296(10) 0.0228(6) Uani 1 1 d . . . H37 H 0.2926 -0.3035 0.0762 0.027 Uiso 1 1 calc R . . C38 C 0.31358(12) -0.1416(3) 0.04432(12) 0.0198(8) Uani 1 1 d . . . C39 C 0.34756(12) -0.2089(3) 0.01711(13) 0.0252(8) Uani 1 1 d . . . H39A H 0.3855 -0.1879 0.0373 0.038 Uiso 1 1 calc R . . H39B H 0.3367 -0.1770 -0.0204 0.038 Uiso 1 1 calc R . . H39C H 0.3424 -0.3053 0.0170 0.038 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 0.0278(14) 0.0296(15) 0.0243(14) -0.0047(12) 0.0063(12) 0.0033(12) O2 0.0271(15) 0.0365(16) 0.0293(15) 0.0035(12) 0.0049(12) -0.0012(12) O3 0.043(2) 0.029(2) 0.033(2) 0.000 0.0095(17) 0.000 Cl4 0.0217(5) 0.0204(5) 0.0314(5) -0.0014(4) 0.0079(4) -0.0004(4) Cl5 0.0357(5) 0.0214(5) 0.0399(5) 0.0032(4) 0.0243(4) 0.0035(4) Cl6 0.0331(5) 0.0181(5) 0.0312(5) -0.0006(4) 0.0159(4) 0.0009(4) C7 0.0231(18) 0.0192(18) 0.0232(19) 0.0040(15) 0.0102(15) 0.0031(15) C8 0.0217(19) 0.0068(16) 0.0227(19) 0.0017(14) 0.0099(16) 0.0016(14) C9 0.0187(19) 0.0102(17) 0.0227(19) -0.0027(14) 0.0067(15) 0.0014(14) C10 0.0183(18) 0.0175(18) 0.0241(19) 0.0006(15) 0.0058(15) 0.0009(14) C11 0.0170(17) 0.0189(19) 0.0195(19) -0.0006(15) 0.0076(15) -0.0012(15) C12 0.0200(18) 0.0182(19) 0.0217(19) -0.0020(16) 0.0104(15) -0.0019(15) C13 0.0254(19) 0.0191(19) 0.027(2) 0.0022(15) 0.0084(16) 0.0027(15) N14 0.0212(15) 0.0152(15) 0.0251(16) -0.0008(13) 0.0061(14) 0.0024(12) N15 0.0204(15) 0.0224(17) 0.0164(15) -0.0023(13) 0.0027(13) -0.0024(13) C16 0.0188(18) 0.018(2) 0.0234(19) 0.0000(15) 0.0106(16) -0.0012(15) C17 0.0241(19) 0.0259(19) 0.0245(19) -0.0010(16) 0.0096(16) -0.0001(16) C18 0.0248(19) 0.0199(18) 0.0298(19) 0.0001(15) 0.0138(16) -0.0021(15) C19 0.0172(18) 0.0078(17) 0.0255(19) 0.0006(14) 0.0096(16) 0.0018(13) C20 0.0208(19) 0.0097(17) 0.0216(18) -0.0007(14) 0.0107(16) 0.0013(14) C21 0.0229(18) 0.0183(19) 0.0260(19) 0.0004(15) 0.0114(15) 0.0015(15) C22 0.0190(18) 0.0202(19) 0.0201(19) 0.0008(15) 0.0104(16) -0.0022(15) C23 0.0196(18) 0.022(2) 0.0209(19) 0.0027(16) 0.0097(16) -0.0009(15) C24 0.034(2) 0.0222(19) 0.0246(19) -0.0001(16) 0.0079(16) 0.0017(16) N25 0.0278(16) 0.0176(15) 0.0247(17) -0.0014(14) 0.0124(14) 0.0018(13) N26 0.0296(16) 0.0245(17) 0.0170(15) -0.0034(14) 0.0092(13) -0.0019(14) C27 0.0245(19) 0.0167(19) 0.028(2) 0.0013(16) 0.0133(16) 0.0011(16) C28 0.048(2) 0.022(2) 0.027(2) 0.0000(16) 0.0130(18) 0.0026(17) C29 0.0216(18) 0.0202(18) 0.0258(19) -0.0015(15) 0.0103(16) 0.0021(15) C30 0.0196(18) 0.0112(17) 0.0191(18) 0.0019(14) 0.0057(15) 0.0039(14) C31 0.0193(18) 0.0084(17) 0.0229(19) 0.0029(14) 0.0094(16) -0.0004(14) C32 0.0224(18) 0.0140(17) 0.0236(18) 0.0011(14) 0.0090(15) 0.0009(14) C33 0.0109(16) 0.021(2) 0.0199(18) 0.0023(14) 0.0041(14) 0.0001(14) C34 0.0232(19) 0.019(2) 0.030(2) 0.0023(15) 0.0112(16) 0.0006(15) C35 0.047(2) 0.025(2) 0.055(3) 0.0017(18) 0.036(2) 0.0006(18) N36 0.0276(16) 0.0241(17) 0.0349(17) 0.0019(14) 0.0220(14) 0.0003(13) N37 0.0218(15) 0.0178(15) 0.0312(16) -0.0001(13) 0.0129(14) 0.0006(13) C38 0.0143(17) 0.022(2) 0.0209(18) 0.0008(15) 0.0042(15) -0.0032(15) C39 0.0230(19) 0.0235(19) 0.029(2) -0.0007(15) 0.0094(16) 0.0010(15) _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 H1A 0.883(19) . ? O1 H1B 0.884(19) . ? O2 H2A 0.873(19) . ? O2 H2B 0.88(2) . ? C7 C8 1.517(4) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 C9 1.400(4) . ? C8 C31 1.406(4) . ? C9 C19 1.399(4) . ? C9 C10 1.528(4) . ? C10 C11 1.512(4) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.396(4) . ? C11 C16 1.398(4) . ? C12 N14 1.339(4) . ? C12 C13 1.487(4) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? N14 N15 1.335(3) . ? N14 H14 0.8600 . ? N15 C16 1.341(4) . ? N15 H15 0.8600 . ? C16 C17 1.487(4) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 C19 1.520(4) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 C20 1.407(4) . ? C20 C30 1.399(4) . ? C20 C21 1.521(4) . ? C21 C22 1.510(4) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C23 1.393(4) . ? C22 C27 1.394(4) . ? C23 N25 1.345(4) . ? C23 C24 1.483(4) . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? N25 N26 1.343(3) . ? N25 H25 0.8600 . ? N26 C27 1.346(4) . ? N26 H26 0.8600 . ? C27 C28 1.485(4) . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 C30 1.512(4) . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C30 C31 1.400(4) . ? C31 C32 1.523(4) . ? C32 C33 1.505(4) . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C33 C34 1.386(4) . ? C33 C38 1.393(4) . ? C34 N36 1.348(4) . ? C34 C35 1.487(4) . ? C35 H35A 0.9600 . ? C35 H35B 0.9600 . ? C35 H35C 0.9600 . ? N36 N37 1.342(3) . ? N36 H36 0.8600 . ? N37 C38 1.343(4) . ? N37 H37 0.8600 . ? C38 C39 1.488(4) . ? C39 H39A 0.9600 . ? C39 H39B 0.9600 . ? C39 H39C 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 H1A O1 H1B 105(4) . . ? H2A O2 H2B 107(4) . . ? C8 C7 H7A 109.5 . . ? C8 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C8 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C9 C8 C31 120.5(3) . . ? C9 C8 C7 120.9(3) . . ? C31 C8 C7 118.6(3) . . ? C19 C9 C8 119.6(3) . . ? C19 C9 C10 121.9(3) . . ? C8 C9 C10 118.5(3) . . ? C11 C10 C9 116.3(2) . . ? C11 C10 H10A 108.2 . . ? C9 C10 H10A 108.2 . . ? C11 C10 H10B 108.2 . . ? C9 C10 H10B 108.2 . . ? H10A C10 H10B 107.4 . . ? C12 C11 C16 105.6(3) . . ? C12 C11 C10 130.7(3) . . ? C16 C11 C10 123.7(3) . . ? N14 C12 C11 107.8(3) . . ? N14 C12 C13 119.0(3) . . ? C11 C12 C13 133.1(3) . . ? 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 . . ? N15 N14 C12 109.5(2) . . ? N15 N14 H14 125.3 . . ? C12 N14 H14 125.3 . . ? N14 N15 C16 109.3(2) . . ? N14 N15 H15 125.4 . . ? C16 N15 H15 125.4 . . ? N15 C16 C11 107.8(3) . . ? N15 C16 C17 122.0(3) . . ? C11 C16 C17 130.1(3) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C19 C18 H18A 109.5 . . ? C19 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C19 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C9 C19 C20 119.9(3) . . ? C9 C19 C18 121.3(3) . . ? C20 C19 C18 118.8(3) . . ? C30 C20 C19 120.2(3) . . ? C30 C20 C21 118.6(3) . . ? C19 C20 C21 121.2(3) . . ? C22 C21 C20 114.3(2) . . ? C22 C21 H21A 108.7 . . ? C20 C21 H21A 108.7 . . ? C22 C21 H21B 108.7 . . ? C20 C21 H21B 108.7 . . ? H21A C21 H21B 107.6 . . ? C23 C22 C27 106.0(3) . . ? C23 C22 C21 127.5(3) . . ? C27 C22 C21 126.5(3) . . ? N25 C23 C22 108.0(3) . . ? N25 C23 C24 120.0(3) . . ? C22 C23 C24 132.0(3) . . ? 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 . . ? N26 N25 C23 109.0(2) . . ? N26 N25 H25 125.5 . . ? C23 N25 H25 125.5 . . ? N25 N26 C27 109.3(2) . . ? N25 N26 H26 125.4 . . ? C27 N26 H26 125.4 . . ? N26 C27 C22 107.7(3) . . ? N26 C27 C28 121.7(3) . . ? C22 C27 C28 130.6(3) . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C30 C29 H29A 109.5 . . ? C30 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C30 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C20 C30 C31 119.8(3) . . ? C20 C30 C29 119.3(3) . . ? C31 C30 C29 120.8(3) . . ? C30 C31 C8 119.6(3) . . ? C30 C31 C32 121.3(3) . . ? C8 C31 C32 119.0(3) . . ? C33 C32 C31 117.3(2) . . ? C33 C32 H32A 108.0 . . ? C31 C32 H32A 108.0 . . ? C33 C32 H32B 108.0 . . ? C31 C32 H32B 108.0 . . ? H32A C32 H32B 107.2 . . ? C34 C33 C38 106.1(3) . . ? C34 C33 C32 124.3(3) . . ? C38 C33 C32 129.6(3) . . ? N36 C34 C33 107.9(3) . . ? N36 C34 C35 121.7(3) . . ? C33 C34 C35 130.4(3) . . ? C34 C35 H35A 109.5 . . ? C34 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C34 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? N37 N36 C34 109.0(2) . . ? N37 N36 H36 125.5 . . ? C34 N36 H36 125.5 . . ? N36 N37 C38 109.1(2) . . ? N36 N37 H37 125.4 . . ? C38 N37 H37 125.4 . . ? N37 C38 C33 107.8(3) . . ? N37 C38 C39 119.5(3) . . ? C33 C38 C39 132.6(3) . . ? C38 C39 H39A 109.5 . . ? C38 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? C38 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N37 H37 Cl4 0.86 2.24 3.083(3) 168.5 1_545 N36 H36 Cl5 0.86 2.27 3.109(3) 166.4 1_545 N26 H26 O2 0.86 1.86 2.668(3) 155.8 1_554 N25 H25 Cl5 0.86 2.28 3.109(3) 163.2 7_565 N15 H15 O1 0.86 1.82 2.667(3) 166.1 1 N14 H14 Cl6 0.86 2.19 3.037(3) 170.3 1 O2 H2B Cl4 0.88(2) 2.33(2) 3.199(3) 169(5) 6_566 O2 H2A Cl5 0.873(19) 2.29(2) 3.155(3) 171(4) 6_566 O1 H1B Cl6 0.884(19) 2.22(2) 3.094(2) 170(4) 2_655 O1 H1A Cl4 0.883(19) 2.23(2) 3.104(3) 169(4) 2_655 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 21.42 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.497 _refine_diff_density_min -0.279 _refine_diff_density_rms 0.050