# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Pradyut Ghosh' _publ_contact_author_email ICPG@IACS.RES.IN _publ_section_title ; Formation of Nitrate Zipped Dimeric Capsule and Un-Zipping by Chloride Doping ; loop_ _publ_author_name 'Pradyut Ghosh' 'M Arunachalam' # Attachment 'complex2.cif' data_complex2' _database_code_depnum_ccdc_archive 'CCDC 711819' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C66 H82 Cl2 N16 O20' _chemical_formula_weight 1490.38 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' 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/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z' _cell_length_a 22.8777(19) _cell_length_b 11.0220(9) _cell_length_c 13.5118(11) _cell_angle_alpha 90.00 _cell_angle_beta 100.711(2) _cell_angle_gamma 90.00 _cell_volume 3347.7(5) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 625 _cell_measurement_theta_min 0.912 _cell_measurement_theta_max 0.973 _exptl_crystal_description BLOCK _exptl_crystal_colour COLORLESS _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.479 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1568 _exptl_absorpt_coefficient_mu 0.187 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9123 _exptl_absorpt_correction_T_max 0.9725 _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 'BRUKER 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 19006 _diffrn_reflns_av_R_equivalents 0.0520 _diffrn_reflns_av_sigmaI/netI 0.0356 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.53 _diffrn_reflns_theta_max 24.86 _reflns_number_total 3047 _reflns_number_gt 2459 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER AXS SMART 3' _computing_cell_refinement 'BRUKER AXS SMART 3' _computing_data_reduction 'BRUKER AXS SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'BRUKER SHELXTL' _computing_publication_material 'MERCURY 1.4' _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^)+(0.1445P)^2^+14.8955P] 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 3047 _refine_ls_number_parameters 269 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0915 _refine_ls_R_factor_gt 0.0767 _refine_ls_wR_factor_ref 0.2449 _refine_ls_wR_factor_gt 0.2300 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.0319(2) 0.0000 0.7172(4) 0.0245(12) Uani 1 2 d S . . H1B H 0.061(3) 0.0000 0.685(6) 0.05(2) Uiso 1 2 d S . . H1A H 0.0057(16) 0.070(3) 0.695(3) 0.016(9) Uiso 1 1 d . . . C2 C 0.0519(2) 0.0000 0.8307(4) 0.0221(11) Uani 1 2 d S . . C3 C 0.06104(14) 0.1097(3) 0.8831(3) 0.0206(8) Uani 1 1 d . . . C4 C 0.05688(16) 0.2276(4) 0.8250(3) 0.0242(9) Uani 1 1 d . . . H4A H 0.0171 0.2363 0.7858 0.029 Uiso 1 1 calc R . . H4B H 0.0639 0.2948 0.8721 0.029 Uiso 1 1 calc R . . N5 N 0.10048(13) 0.2325(3) 0.7570(2) 0.0226(7) Uani 1 1 d . . . C6 C 0.08761(16) 0.2593(4) 0.6598(3) 0.0252(9) Uani 1 1 d . . . H6 H 0.0499 0.2788 0.6246 0.030 Uiso 1 1 calc R . . N7 N 0.13600(15) 0.2545(3) 0.6200(3) 0.0272(8) Uani 1 1 d . . . H7 H 0.130(2) 0.269(4) 0.571(4) 0.028(14) Uiso 1 1 d . . . C8 C 0.18385(16) 0.2222(3) 0.6937(3) 0.0233(8) Uani 1 1 d . . . C9 C 0.24358(17) 0.2034(4) 0.6902(3) 0.0273(9) Uani 1 1 d . . . H9 H 0.2582 0.2126 0.6309 0.033 Uiso 1 1 calc R . . C10 C 0.27997(17) 0.1703(4) 0.7792(3) 0.0292(9) Uani 1 1 d . . . H10 H 0.3201 0.1559 0.7799 0.035 Uiso 1 1 calc R . . C11 C 0.25758(16) 0.1581(4) 0.8689(3) 0.0283(9) Uani 1 1 d . . . H11 H 0.2834 0.1356 0.9276 0.034 Uiso 1 1 calc R . . C12 C 0.19876(16) 0.1782(4) 0.8723(3) 0.0249(8) Uani 1 1 d . . . H12 H 0.1845 0.1719 0.9322 0.030 Uiso 1 1 calc R . . C13 C 0.16149(15) 0.2087(3) 0.7821(3) 0.0222(8) Uani 1 1 d . . . C14 C 0.07532(14) 0.1107(4) 0.9885(3) 0.0229(8) Uani 1 1 d . . . C15 C 0.08548(17) 0.2288(4) 1.0462(3) 0.0278(9) Uani 1 1 d . . . H15C H 0.1045 0.2858 1.0088 0.042 Uiso 1 1 calc R . . H15A H 0.1105 0.2144 1.1105 0.042 Uiso 1 1 calc R . . H15B H 0.0480 0.2610 1.0560 0.042 Uiso 1 1 calc R . . C16 C 0.0804(2) 0.0000 1.0406(4) 0.0220(11) Uani 1 2 d S . . C17 C 0.0917(2) 0.0000 1.1544(4) 0.0252(12) Uani 1 2 d S . . H17 H 0.0712(18) 0.071(4) 1.175(3) 0.025(10) Uiso 1 1 d . . . N18 N 0.15627(18) 0.0000 1.1984(3) 0.0242(10) Uani 1 2 d S . . C19 C 0.2013(2) 0.0000 1.1483(4) 0.0255(12) Uani 1 2 d S . . H19 H 0.1970 0.0000 1.0785 0.031 Uiso 1 2 calc SR . . N20 N 0.2530(2) 0.0000 1.2116(4) 0.0275(11) Uani 1 2 d S . . H20 H 0.284(4) 0.0000 1.199(6) 0.06(2) Uiso 1 2 d S . . C21 C 0.2420(2) 0.0000 1.3091(4) 0.0300(13) Uani 1 2 d S . . C22 C 0.2793(3) 0.0000 1.4015(4) 0.0311(13) Uani 1 2 d S . . H22 H 0.3204 0.0000 1.4071 0.037 Uiso 1 2 calc SR . . C23 C 0.2533(3) 0.0000 1.4844(5) 0.0375(15) Uani 1 2 d S . . H23 H 0.2775 0.0000 1.5479 0.045 Uiso 1 2 calc SR . . C24 C 0.1915(3) 0.0000 1.4769(4) 0.0347(14) Uani 1 2 d S . . H24 H 0.1756 0.0000 1.5355 0.042 Uiso 1 2 calc SR . . C25 C 0.1533(3) 0.0000 1.3843(4) 0.0298(13) Uani 1 2 d S . . H25 H 0.1122 0.0000 1.3790 0.036 Uiso 1 2 calc SR . . C26 C 0.1796(2) 0.0000 1.3009(4) 0.0250(12) Uani 1 2 d S . . N27 N 0.40896(13) 0.2319(3) 0.6241(2) 0.0239(7) Uani 1 1 d . . . O28 O 0.41612(14) 0.2405(3) 0.7162(2) 0.0442(9) Uani 1 1 d . . . O29 O 0.44821(13) 0.2618(4) 0.5770(2) 0.0510(10) Uani 1 1 d . . . O30 O 0.35960(12) 0.1943(3) 0.57470(19) 0.0349(7) Uani 1 1 d . . . Cl31 Cl 0.35790(7) 0.0000 0.10501(12) 0.0372(5) Uani 1 2 d S . . O32 O 0.4338(4) 0.0000 0.8101(7) 0.118(3) Uiso 1 2 d S . . O33 O 0.0397(8) 0.5000 0.5106(17) 0.292(10) Uiso 1 2 d S . . O34 O 0.5274(10) 0.0000 0.9800(19) 0.299(11) Uiso 1 2 d S . . O35 O 1.0299(6) 0.5000 0.7031(9) 0.160(4) Uiso 1 2 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.019(3) 0.036(3) 0.019(3) 0.000 0.003(2) 0.000 C2 0.013(2) 0.037(3) 0.018(2) 0.000 0.0065(19) 0.000 C3 0.0106(16) 0.032(2) 0.0201(17) 0.0005(15) 0.0054(13) -0.0013(14) C4 0.0150(18) 0.038(2) 0.0206(18) -0.0018(16) 0.0063(14) 0.0005(15) N5 0.0159(15) 0.0326(18) 0.0199(15) 0.0021(13) 0.0049(12) -0.0006(13) C6 0.0200(19) 0.033(2) 0.0219(19) 0.0021(16) 0.0025(15) -0.0005(16) N7 0.0256(18) 0.040(2) 0.0174(17) 0.0027(15) 0.0067(14) -0.0026(14) C8 0.0221(19) 0.025(2) 0.0228(18) -0.0025(15) 0.0050(14) -0.0026(15) C9 0.025(2) 0.027(2) 0.033(2) -0.0052(16) 0.0142(16) -0.0054(16) C10 0.0184(19) 0.029(2) 0.041(2) -0.0055(17) 0.0053(16) -0.0027(15) C11 0.0200(19) 0.032(2) 0.032(2) 0.0014(17) 0.0007(15) -0.0009(16) C12 0.0209(19) 0.029(2) 0.0248(18) 0.0012(16) 0.0037(15) -0.0042(15) C13 0.0155(18) 0.0254(19) 0.0267(18) -0.0033(15) 0.0064(14) -0.0029(14) C14 0.0107(16) 0.037(2) 0.0218(18) -0.0015(16) 0.0055(13) -0.0013(15) C15 0.0254(19) 0.038(2) 0.0206(18) -0.0038(16) 0.0067(15) -0.0035(17) C16 0.010(2) 0.037(3) 0.020(2) 0.000 0.0052(19) 0.000 C17 0.013(2) 0.043(3) 0.019(3) 0.000 0.002(2) 0.000 N18 0.014(2) 0.036(3) 0.020(2) 0.000 -0.0001(17) 0.000 C19 0.018(3) 0.034(3) 0.025(3) 0.000 0.005(2) 0.000 N20 0.017(2) 0.032(3) 0.032(3) 0.000 0.002(2) 0.000 C21 0.027(3) 0.021(3) 0.037(3) 0.000 -0.007(2) 0.000 C22 0.026(3) 0.026(3) 0.036(3) 0.000 -0.006(2) 0.000 C23 0.043(4) 0.029(3) 0.032(3) 0.000 -0.015(3) 0.000 C24 0.052(4) 0.027(3) 0.024(3) 0.000 0.004(3) 0.000 C25 0.034(3) 0.029(3) 0.025(3) 0.000 0.002(2) 0.000 C26 0.025(3) 0.024(3) 0.023(3) 0.000 -0.004(2) 0.000 N27 0.0176(16) 0.0368(19) 0.0170(15) -0.0009(13) 0.0025(12) -0.0044(13) O28 0.0343(17) 0.074(2) 0.0235(15) -0.0085(15) 0.0035(12) -0.0076(16) O29 0.0235(16) 0.097(3) 0.0322(16) 0.0093(17) 0.0050(13) -0.0130(16) O30 0.0255(15) 0.055(2) 0.0242(14) -0.0018(13) 0.0045(11) -0.0108(13) Cl31 0.0336(8) 0.0341(8) 0.0471(9) 0.000 0.0160(7) 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 C1 C2 1.517(7) . ? C1 H1B 0.86(8) . ? C1 H1A 0.99(4) . ? C2 C3 1.397(4) . ? C2 C3 1.397(4) 6 ? C3 C14 1.401(5) . ? C3 C4 1.512(5) . ? C4 N5 1.478(4) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? N5 C6 1.325(5) . ? N5 C13 1.399(5) . ? C6 N7 1.319(5) . ? C6 H6 0.9300 . ? N7 C8 1.383(5) . ? N7 H7 0.67(5) . ? C8 C13 1.391(5) . ? C8 C9 1.392(5) . ? C9 C10 1.377(6) . ? C9 H9 0.9300 . ? C10 C11 1.408(5) . ? C10 H10 0.9300 . ? C11 C12 1.373(5) . ? C11 H11 0.9300 . ? C12 C13 1.393(5) . ? C12 H12 0.9300 . ? C14 C16 1.402(5) . ? C14 C15 1.513(5) . ? C15 H15C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C16 C14 1.402(5) 6 ? C16 C17 1.511(7) . ? C17 N18 1.486(6) . ? C17 H17 0.98(4) . ? N18 C19 1.334(7) . ? N18 C26 1.388(7) . ? C19 N20 1.324(7) . ? C19 H19 0.9300 . ? N20 C21 1.386(8) . ? N20 H20 0.77(8) . ? C21 C22 1.375(8) . ? C21 C26 1.410(8) . ? C22 C23 1.361(9) . ? C22 H22 0.9300 . ? C23 C24 1.400(9) . ? C23 H23 0.9300 . ? C24 C25 1.387(8) . ? C24 H24 0.9300 . ? C25 C26 1.373(8) . ? C25 H25 0.9300 . ? N27 O28 1.228(4) . ? N27 O29 1.238(4) . ? N27 O30 1.270(4) 1 ? N27 O30 1.270(4) . ? O33 O33 1.78(4) 5_566 ? O34 O34 1.45(4) 5_657 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 H1B 114(5) . . ? C2 C1 H1A 111(2) . . ? H1B C1 H1A 109(3) . . ? C3 C2 C3 119.9(4) . 6 ? C3 C2 C1 120.0(2) . . ? C3 C2 C1 120.0(2) 6 . ? C2 C3 C14 120.4(3) . . ? C2 C3 C4 119.5(3) . . ? C14 C3 C4 120.1(3) . . ? N5 C4 C3 111.7(3) . . ? N5 C4 H4A 109.3 . . ? C3 C4 H4A 109.3 . . ? N5 C4 H4B 109.3 . . ? C3 C4 H4B 109.3 . . ? H4A C4 H4B 107.9 . . ? C6 N5 C13 108.1(3) . . ? C6 N5 C4 125.0(3) . . ? C13 N5 C4 126.9(3) . . ? N7 C6 N5 110.3(3) . . ? N7 C6 H6 124.9 . . ? N5 C6 H6 124.9 . . ? C6 N7 C8 109.2(3) . . ? C6 N7 H7 112(4) . . ? C8 N7 H7 139(4) . . ? N7 C8 C13 106.1(3) . . ? N7 C8 C9 131.7(3) . . ? C13 C8 C9 122.2(3) . . ? C10 C9 C8 116.6(3) . . ? C10 C9 H9 121.7 . . ? C8 C9 H9 121.7 . . ? C9 C10 C11 121.3(4) . . ? C9 C10 H10 119.4 . . ? C11 C10 H10 119.4 . . ? C12 C11 C10 122.0(4) . . ? C12 C11 H11 119.0 . . ? C10 C11 H11 119.0 . . ? C11 C12 C13 117.0(3) . . ? C11 C12 H12 121.5 . . ? C13 C12 H12 121.5 . . ? C8 C13 C12 120.9(3) . . ? C8 C13 N5 106.3(3) . . ? C12 C13 N5 132.7(3) . . ? C3 C14 C16 119.0(3) . . ? C3 C14 C15 121.0(3) . . ? C16 C14 C15 119.9(3) . . ? C14 C15 H15C 109.5 . . ? C14 C15 H15A 109.5 . . ? H15C C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15C C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C16 C14 120.9(4) 6 . ? C14 C16 C17 119.6(2) 6 . ? C14 C16 C17 119.6(2) . . ? N18 C17 C16 112.2(4) . . ? N18 C17 H17 112(2) . . ? C16 C17 H17 107(2) . . ? C19 N18 C26 108.4(4) . . ? C19 N18 C17 126.9(4) . . ? C26 N18 C17 124.7(4) . . ? N20 C19 N18 110.7(5) . . ? N20 C19 H19 124.7 . . ? N18 C19 H19 124.7 . . ? C19 N20 C21 108.4(5) . . ? C19 N20 H20 128(6) . . ? C21 N20 H20 124(6) . . ? C22 C21 N20 132.2(6) . . ? C22 C21 C26 121.2(6) . . ? N20 C21 C26 106.6(5) . . ? C23 C22 C21 117.1(6) . . ? C23 C22 H22 121.4 . . ? C21 C22 H22 121.4 . . ? C22 C23 C24 122.0(5) . . ? C22 C23 H23 119.0 . . ? C24 C23 H23 119.0 . . ? C25 C24 C23 121.6(6) . . ? C25 C24 H24 119.2 . . ? C23 C24 H24 119.2 . . ? C26 C25 C24 116.2(6) . . ? C26 C25 H25 121.9 . . ? C24 C25 H25 121.9 . . ? C25 C26 N18 132.2(5) . . ? C25 C26 C21 121.8(5) . . ? N18 C26 C21 105.9(5) . . ? O28 N27 O29 121.8(3) . . ? O28 N27 O30 119.7(3) . 1 ? O29 N27 O30 118.4(3) . 1 ? O28 N27 O30 119.7(3) . . ? O29 N27 O30 118.4(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 C17 H17 O28 0.98(4) 2.53(4) 3.375(4) 144(3) 7_557 C15 H15A O28 0.96 2.57 3.235(5) 126.1 7_557 C9 H9 O30 0.93 2.58 3.322(4) 137.1 1 C6 H6 O29 0.93 2.34 3.186(5) 151.4 8_455 C4 H4A O28 0.97 2.34 3.301(5) 170.8 8_455 N20 H20 Cl31 0.77(8) 2.29(8) 3.020(5) 160(8) 1_556 N7 H7 O30 0.67(5) 2.06(5) 2.710(4) 163(5) 7_556 N7 H7 O29 0.67(5) 2.45(5) 2.987(5) 139(5) 7_556 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 24.86 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.323 _refine_diff_density_min -0.789 _refine_diff_density_rms 0.101 # Attachment 'complex3.cif' data_complex3 _database_code_depnum_ccdc_archive 'CCDC 711820' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H39 Cl4 N6 O3' _chemical_formula_weight 709.50 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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 10.2508(5) _cell_length_b 10.3104(5) _cell_length_c 20.0734(10) _cell_angle_alpha 82.4230(10) _cell_angle_beta 80.8690(10) _cell_angle_gamma 74.6420(10) _cell_volume 2010.86(17) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 708 _cell_measurement_theta_min 0.907 _cell_measurement_theta_max 0.937 _exptl_crystal_description BLOCK _exptl_crystal_colour COLORLESS _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.172 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 742 _exptl_absorpt_coefficient_mu 0.331 _exptl_absorpt_correction_type 'MULTI SCAN' _exptl_absorpt_correction_T_min 0.9071 _exptl_absorpt_correction_T_max 0.9367 _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 'BRUKER SMART 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 31194 _diffrn_reflns_av_R_equivalents 0.0266 _diffrn_reflns_av_sigmaI/netI 0.0367 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 31.95 _reflns_number_total 11720 _reflns_number_gt 8989 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER AXS SMART 2' _computing_cell_refinement 'BRUKER AXS SMART 2' _computing_data_reduction 'BRUKER AXS SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'BRUKER SHELXTL' _computing_publication_material 'MERCURY 1.4' _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^)+(0.1024P)^2^+1.0986P] 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 11720 _refine_ls_number_parameters 418 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0817 _refine_ls_R_factor_gt 0.0647 _refine_ls_wR_factor_ref 0.1893 _refine_ls_wR_factor_gt 0.1772 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.5478(2) 1.1014(2) 0.41862(10) 0.0265(4) Uani 1 1 d . . . H1C H 0.5578 1.1922 0.4143 0.040 Uiso 1 1 calc R . . H1A H 0.6025 1.0474 0.4518 0.040 Uiso 1 1 calc R . . H1B H 0.4538 1.1016 0.4327 0.040 Uiso 1 1 calc R . . C2 C 0.59409(18) 1.0432(2) 0.35127(9) 0.0186(3) Uani 1 1 d . . . C3 C 0.66408(19) 0.90667(19) 0.34845(9) 0.0196(3) Uani 1 1 d . . . C4 C 0.6760(2) 0.8145(2) 0.41323(10) 0.0250(4) Uani 1 1 d . . . H4B H 0.5973 0.8472 0.4460 0.030 Uiso 1 1 calc R . . H4A H 0.6740 0.7249 0.4042 0.030 Uiso 1 1 calc R . . N5 N 0.80136(18) 0.80434(18) 0.44338(8) 0.0243(3) Uani 1 1 d . . . C6 C 0.8426(2) 0.7174(2) 0.49978(10) 0.0294(5) Uani 1 1 d . . . C7 C 0.7838(3) 0.6221(2) 0.53982(11) 0.0384(6) Uani 1 1 d . . . H7 H 0.7024 0.6061 0.5322 0.046 Uiso 1 1 calc R . . C8 C 0.8566(4) 0.5517(3) 0.59271(13) 0.0536(9) Uani 1 1 d . . . H8 H 0.8227 0.4860 0.6212 0.064 Uiso 1 1 calc R . . C9 C 0.9780(4) 0.5770(3) 0.60391(14) 0.0594(10) Uani 1 1 d . . . H9 H 1.0219 0.5286 0.6400 0.071 Uiso 1 1 calc R . . C10 C 1.0341(3) 0.6700(3) 0.56395(13) 0.0511(8) Uani 1 1 d . . . H10 H 1.1154 0.6858 0.5717 0.061 Uiso 1 1 calc R . . C11 C 0.9649(3) 0.7406(3) 0.51085(12) 0.0360(5) Uani 1 1 d . . . N12 N 0.9930(2) 0.8387(2) 0.46160(10) 0.0354(4) Uani 1 1 d . . . H12 H 1.0632 0.8715 0.4569 0.042 Uiso 1 1 calc R . . C13 C 0.8941(2) 0.8745(2) 0.42231(11) 0.0283(4) Uani 1 1 d . . . H13 H 0.8904 0.9394 0.3853 0.034 Uiso 1 1 calc R . . C14 C 0.71466(19) 0.85397(19) 0.28595(10) 0.0207(4) Uani 1 1 d . . . C15 C 0.8000(3) 0.7115(2) 0.28281(12) 0.0341(5) Uani 1 1 d . . . H15B H 0.7438 0.6538 0.2769 0.051 Uiso 1 1 calc R . . H15A H 0.8393 0.6814 0.3242 0.051 Uiso 1 1 calc R . . H15C H 0.8715 0.7081 0.2454 0.051 Uiso 1 1 calc R . . C16 C 0.68679(18) 0.93627(19) 0.22627(9) 0.0189(3) Uani 1 1 d . . . C17 C 0.7262(2) 0.8759(2) 0.15927(10) 0.0230(4) Uani 1 1 d . . . H17A H 0.7263 0.7810 0.1666 0.028 Uiso 1 1 calc R . . H17B H 0.6583 0.9204 0.1296 0.028 Uiso 1 1 calc R . . N18 N 0.86223(17) 0.88879(17) 0.12548(8) 0.0206(3) Uani 1 1 d . . . C19 C 0.9246(2) 0.8351(2) 0.06485(9) 0.0220(4) Uani 1 1 d . . . C20 C 0.8791(2) 0.7646(2) 0.02278(11) 0.0297(4) Uani 1 1 d . . . H20 H 0.7924 0.7489 0.0311 0.036 Uiso 1 1 calc R . . C21 C 0.9720(3) 0.7192(3) -0.03270(12) 0.0393(6) Uani 1 1 d . . . H21 H 0.9468 0.6715 -0.0627 0.047 Uiso 1 1 calc R . . C22 C 1.1026(3) 0.7432(3) -0.04492(12) 0.0393(6) Uani 1 1 d . . . H22 H 1.1613 0.7101 -0.0826 0.047 Uiso 1 1 calc R . . C23 C 1.1470(2) 0.8140(2) -0.00324(11) 0.0310(5) Uani 1 1 d . . . H23 H 1.2336 0.8298 -0.0116 0.037 Uiso 1 1 calc R . . C24 C 1.0534(2) 0.8605(2) 0.05239(10) 0.0235(4) Uani 1 1 d . . . N25 N 1.06416(18) 0.92951(18) 0.10523(9) 0.0252(3) Uani 1 1 d . . . H25 H 1.1337 0.9579 0.1097 0.030 Uiso 1 1 calc R . . C26 C 0.9486(2) 0.9445(2) 0.14790(10) 0.0231(4) Uani 1 1 d . . . H26 H 0.9308 0.9875 0.1875 0.028 Uiso 1 1 calc R . . C27 C 0.61620(18) 1.07198(19) 0.22781(9) 0.0180(3) Uani 1 1 d . . . C28 C 0.5900(2) 1.1628(2) 0.16362(10) 0.0253(4) Uani 1 1 d . . . H28C H 0.6509 1.1228 0.1261 0.038 Uiso 1 1 calc R . . H28A H 0.6051 1.2492 0.1679 0.038 Uiso 1 1 calc R . . H28B H 0.4974 1.1742 0.1559 0.038 Uiso 1 1 calc R . . C29 C 0.56949(17) 1.12437(18) 0.29110(9) 0.0174(3) Uani 1 1 d . . . C30 C 0.48486(19) 1.2680(2) 0.29207(10) 0.0216(4) Uani 1 1 d . . . H30B H 0.4772 1.2979 0.3367 0.026 Uiso 1 1 calc R . . H30A H 0.5290 1.3265 0.2595 0.026 Uiso 1 1 calc R . . N31 N 0.34761(16) 1.27719(16) 0.27498(8) 0.0193(3) Uani 1 1 d . . . C32 C 0.2760(2) 1.3756(2) 0.23089(10) 0.0219(4) Uani 1 1 d . . . C33 C 0.3098(2) 1.4866(2) 0.19158(13) 0.0328(5) Uani 1 1 d . . . H33 H 0.3916 1.5089 0.1925 0.039 Uiso 1 1 calc R . . C34 C 0.2138(3) 1.5616(3) 0.15098(14) 0.0430(6) Uani 1 1 d . . . H34 H 0.2320 1.6363 0.1235 0.052 Uiso 1 1 calc R . . C35 C 0.0902(3) 1.5287(3) 0.14985(14) 0.0416(6) Uani 1 1 d . . . H35 H 0.0291 1.5822 0.1216 0.050 Uiso 1 1 calc R . . C36 C 0.0565(2) 1.4198(2) 0.18919(12) 0.0320(5) Uani 1 1 d . . . H36 H -0.0262 1.3989 0.1889 0.038 Uiso 1 1 calc R . . C37 C 0.1534(2) 1.3427(2) 0.22941(10) 0.0236(4) Uani 1 1 d . . . N38 N 0.15543(17) 1.22613(19) 0.27284(9) 0.0255(4) Uani 1 1 d . . . H38 H 0.0916 1.1842 0.2812 0.031 Uiso 1 1 calc R . . C39 C 0.2716(2) 1.1899(2) 0.29931(10) 0.0230(4) Uani 1 1 d . . . H39 H 0.2966 1.1150 0.3302 0.028 Uiso 1 1 calc R . . Cl40 Cl 0.91797(5) 0.10421(5) 0.28826(3) 0.02662(12) Uani 1 1 d . . . Cl41 Cl 0.26610(6) 0.92538(6) 0.43249(3) 0.03539(14) Uani 1 1 d . . . Cl42 Cl 0.67562(6) 0.52046(6) 0.15361(3) 0.03758(15) Uani 1 1 d . . . Cl43 Cl 0.34078(7) 0.99772(8) 0.11098(5) 0.0558(2) Uani 1 1 d . . . O44 O 0.5815(3) 0.5569(2) 0.01386(11) 0.0550(6) Uani 1 1 d . . . O45 O 0.4517(3) 0.7563(3) 0.21709(17) 0.0787(8) Uani 1 1 d . . . O46 O 0.5047(3) 0.8192(2) 0.99500(11) 0.0592(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0268(10) 0.0310(11) 0.0198(9) -0.0032(8) -0.0023(7) -0.0041(8) C2 0.0144(7) 0.0246(9) 0.0187(8) -0.0024(7) -0.0008(6) -0.0089(7) C3 0.0192(8) 0.0216(9) 0.0197(8) 0.0015(7) -0.0039(6) -0.0087(7) C4 0.0308(10) 0.0247(10) 0.0222(9) 0.0049(7) -0.0074(8) -0.0128(8) N5 0.0297(9) 0.0206(8) 0.0213(8) 0.0029(6) -0.0081(7) -0.0035(7) C6 0.0406(12) 0.0213(10) 0.0187(9) -0.0012(7) -0.0062(8) 0.0065(8) C7 0.0618(16) 0.0209(11) 0.0235(10) 0.0005(8) -0.0008(10) 0.0012(10) C8 0.092(2) 0.0251(13) 0.0241(11) 0.0012(9) 0.0006(13) 0.0127(14) C9 0.072(2) 0.0511(18) 0.0301(13) -0.0063(12) -0.0183(13) 0.0362(16) C10 0.0486(16) 0.0590(18) 0.0294(12) -0.0117(12) -0.0153(11) 0.0246(14) C11 0.0363(12) 0.0366(13) 0.0272(11) -0.0087(9) -0.0098(9) 0.0106(10) N12 0.0274(9) 0.0441(12) 0.0334(10) -0.0062(9) -0.0106(8) -0.0015(8) C13 0.0249(10) 0.0318(11) 0.0276(10) -0.0003(8) -0.0083(8) -0.0046(8) C14 0.0216(9) 0.0185(9) 0.0241(9) -0.0020(7) -0.0037(7) -0.0081(7) C15 0.0503(14) 0.0181(10) 0.0302(11) -0.0029(8) -0.0049(10) -0.0019(9) C16 0.0176(8) 0.0223(9) 0.0194(8) -0.0039(7) -0.0011(6) -0.0094(7) C17 0.0233(9) 0.0271(10) 0.0218(9) -0.0056(7) -0.0001(7) -0.0120(8) N18 0.0238(8) 0.0205(8) 0.0178(7) -0.0031(6) -0.0006(6) -0.0070(6) C19 0.0264(9) 0.0179(9) 0.0185(8) -0.0008(7) -0.0010(7) -0.0017(7) C20 0.0362(11) 0.0311(11) 0.0221(9) -0.0054(8) -0.0042(8) -0.0074(9) C21 0.0507(15) 0.0404(14) 0.0257(11) -0.0120(10) -0.0028(10) -0.0064(11) C22 0.0441(14) 0.0394(13) 0.0255(11) -0.0061(9) 0.0053(10) 0.0005(11) C23 0.0293(10) 0.0291(11) 0.0255(10) 0.0028(8) 0.0035(8) 0.0020(9) C24 0.0270(10) 0.0194(9) 0.0201(9) 0.0025(7) -0.0006(7) -0.0025(7) N25 0.0240(8) 0.0244(9) 0.0279(9) -0.0022(7) 0.0000(7) -0.0092(7) C26 0.0252(9) 0.0218(9) 0.0233(9) -0.0031(7) -0.0009(7) -0.0083(7) C27 0.0162(8) 0.0214(9) 0.0186(8) 0.0000(7) -0.0028(6) -0.0089(7) C28 0.0264(10) 0.0287(10) 0.0211(9) 0.0012(8) -0.0053(7) -0.0077(8) C29 0.0134(7) 0.0176(8) 0.0223(8) -0.0017(7) -0.0037(6) -0.0048(6) C30 0.0169(8) 0.0199(9) 0.0289(10) -0.0024(7) -0.0058(7) -0.0047(7) N31 0.0157(7) 0.0182(8) 0.0241(8) 0.0009(6) -0.0046(6) -0.0045(6) C32 0.0199(8) 0.0201(9) 0.0238(9) -0.0029(7) -0.0039(7) -0.0010(7) C33 0.0320(11) 0.0228(10) 0.0412(13) 0.0035(9) -0.0051(9) -0.0056(9) C34 0.0486(15) 0.0295(13) 0.0435(14) 0.0089(10) -0.0109(12) 0.0002(11) C35 0.0413(14) 0.0345(13) 0.0412(14) -0.0032(11) -0.0178(11) 0.0113(10) C36 0.0221(10) 0.0382(13) 0.0319(11) -0.0103(9) -0.0087(8) 0.0054(9) C37 0.0183(8) 0.0247(10) 0.0263(9) -0.0067(8) -0.0035(7) -0.0005(7) N38 0.0160(7) 0.0304(9) 0.0317(9) -0.0027(7) -0.0033(6) -0.0086(7) C39 0.0187(8) 0.0238(10) 0.0274(9) 0.0011(7) -0.0040(7) -0.0080(7) Cl40 0.0259(2) 0.0286(3) 0.0308(2) -0.00195(19) -0.00634(18) -0.01507(19) Cl41 0.0292(3) 0.0409(3) 0.0382(3) -0.0066(2) -0.0100(2) -0.0077(2) Cl42 0.0377(3) 0.0325(3) 0.0454(3) -0.0073(2) -0.0090(2) -0.0097(2) Cl43 0.0321(3) 0.0476(4) 0.0918(6) 0.0006(4) -0.0073(3) -0.0208(3) O44 0.0812(16) 0.0476(12) 0.0448(11) -0.0046(9) -0.0239(11) -0.0218(11) O45 0.0681(17) 0.0517(15) 0.116(2) -0.0274(15) -0.0271(16) 0.0047(12) O46 0.0988(19) 0.0430(12) 0.0478(12) 0.0093(9) -0.0211(12) -0.0380(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.508(3) . ? C1 H1C 0.9600 . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C2 C29 1.393(3) . ? C2 C3 1.404(3) . ? C3 C14 1.401(3) . ? C3 C4 1.507(3) . ? C4 N5 1.479(3) . ? C4 H4B 0.9700 . ? C4 H4A 0.9700 . ? N5 C13 1.327(3) . ? N5 C6 1.396(3) . ? C6 C7 1.388(4) . ? C6 C11 1.393(4) . ? C7 C8 1.405(4) . ? C7 H7 0.9300 . ? C8 C9 1.395(6) . ? C8 H8 0.9300 . ? C9 C10 1.355(5) . ? C9 H9 0.9300 . ? C10 C11 1.390(3) . ? C10 H10 0.9300 . ? C11 N12 1.372(4) . ? N12 C13 1.328(3) . ? N12 H12 0.8600 . ? C13 H13 0.9300 . ? C14 C16 1.396(3) . ? C14 C15 1.501(3) . ? C15 H15B 0.9600 . ? C15 H15A 0.9600 . ? C15 H15C 0.9600 . ? C16 C27 1.397(3) . ? C16 C17 1.508(2) . ? C17 N18 1.482(2) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? N18 C26 1.335(2) . ? N18 C19 1.393(2) . ? C19 C20 1.388(3) . ? C19 C24 1.391(3) . ? C20 C21 1.390(3) . ? C20 H20 0.9300 . ? C21 C22 1.403(4) . ? C21 H21 0.9300 . ? C22 C23 1.377(4) . ? C22 H22 0.9300 . ? C23 C24 1.398(3) . ? C23 H23 0.9300 . ? C24 N25 1.386(3) . ? N25 C26 1.333(3) . ? N25 H25 0.8600 . ? C26 H26 0.9300 . ? C27 C29 1.409(2) . ? C27 C28 1.506(3) . ? C28 H28C 0.9600 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C29 C30 1.506(3) . ? C30 N31 1.477(2) . ? C30 H30B 0.9700 . ? C30 H30A 0.9700 . ? N31 C39 1.338(2) . ? N31 C32 1.388(3) . ? C32 C37 1.391(3) . ? C32 C33 1.392(3) . ? C33 C34 1.384(4) . ? C33 H33 0.9300 . ? C34 C35 1.399(4) . ? C34 H34 0.9300 . ? C35 C36 1.374(4) . ? C35 H35 0.9300 . ? C36 C37 1.392(3) . ? C36 H36 0.9300 . ? C37 N38 1.386(3) . ? N38 C39 1.324(3) . ? N38 H38 0.8600 . ? C39 H39 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 H1C 109.5 . . ? C2 C1 H1A 109.5 . . ? H1C C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1C C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C29 C2 C3 119.22(16) . . ? C29 C2 C1 120.48(17) . . ? C3 C2 C1 120.29(17) . . ? C14 C3 C2 120.58(17) . . ? C14 C3 C4 119.92(17) . . ? C2 C3 C4 119.37(17) . . ? N5 C4 C3 113.78(16) . . ? N5 C4 H4B 108.8 . . ? C3 C4 H4B 108.8 . . ? N5 C4 H4A 108.8 . . ? C3 C4 H4A 108.8 . . ? H4B C4 H4A 107.7 . . ? C13 N5 C6 107.91(19) . . ? C13 N5 C4 126.91(17) . . ? C6 N5 C4 125.18(18) . . ? C7 C6 C11 122.6(2) . . ? C7 C6 N5 131.1(2) . . ? C11 C6 N5 106.3(2) . . ? C6 C7 C8 114.8(3) . . ? C6 C7 H7 122.6 . . ? C8 C7 H7 122.6 . . ? C9 C8 C7 122.1(3) . . ? C9 C8 H8 118.9 . . ? C7 C8 H8 118.9 . . ? C10 C9 C8 122.1(3) . . ? C10 C9 H9 118.9 . . ? C8 C9 H9 118.9 . . ? C9 C10 C11 117.1(3) . . ? C9 C10 H10 121.5 . . ? C11 C10 H10 121.5 . . ? N12 C11 C10 132.0(3) . . ? N12 C11 C6 106.7(2) . . ? C10 C11 C6 121.2(3) . . ? C13 N12 C11 108.8(2) . . ? C13 N12 H12 125.6 . . ? C11 N12 H12 125.6 . . ? N5 C13 N12 110.3(2) . . ? N5 C13 H13 124.8 . . ? N12 C13 H13 124.8 . . ? C16 C14 C3 119.24(17) . . ? C16 C14 C15 120.12(17) . . ? C3 C14 C15 120.63(18) . . ? C14 C15 H15B 109.5 . . ? C14 C15 H15A 109.5 . . ? H15B C15 H15A 109.5 . . ? C14 C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? C14 C16 C27 121.10(16) . . ? C14 C16 C17 119.52(17) . . ? C27 C16 C17 119.28(17) . . ? N18 C17 C16 112.88(15) . . ? N18 C17 H17A 109.0 . . ? C16 C17 H17A 109.0 . . ? N18 C17 H17B 109.0 . . ? C16 C17 H17B 109.0 . . ? H17A C17 H17B 107.8 . . ? C26 N18 C19 108.26(16) . . ? C26 N18 C17 127.71(16) . . ? C19 N18 C17 123.93(16) . . ? C20 C19 C24 122.77(18) . . ? C20 C19 N18 130.67(19) . . ? C24 C19 N18 106.52(16) . . ? C19 C20 C21 115.3(2) . . ? C19 C20 H20 122.3 . . ? C21 C20 H20 122.3 . . ? C20 C21 C22 122.0(2) . . ? C20 C21 H21 119.0 . . ? C22 C21 H21 119.0 . . ? C23 C22 C21 122.4(2) . . ? C23 C22 H22 118.8 . . ? C21 C22 H22 118.8 . . ? C22 C23 C24 115.7(2) . . ? C22 C23 H23 122.2 . . ? C24 C23 H23 122.2 . . ? N25 C24 C19 106.68(16) . . ? N25 C24 C23 131.5(2) . . ? C19 C24 C23 121.78(19) . . ? C26 N25 C24 108.53(17) . . ? C26 N25 H25 125.7 . . ? C24 N25 H25 125.7 . . ? N25 C26 N18 110.00(17) . . ? N25 C26 H26 125.0 . . ? N18 C26 H26 125.0 . . ? C16 C27 C29 118.83(17) . . ? C16 C27 C28 121.48(16) . . ? C29 C27 C28 119.69(17) . . ? C27 C28 H28C 109.5 . . ? C27 C28 H28A 109.5 . . ? H28C C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28C C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C2 C29 C27 120.90(17) . . ? C2 C29 C30 120.84(16) . . ? C27 C29 C30 118.15(17) . . ? N31 C30 C29 109.88(15) . . ? N31 C30 H30B 109.7 . . ? C29 C30 H30B 109.7 . . ? N31 C30 H30A 109.7 . . ? C29 C30 H30A 109.7 . . ? H30B C30 H30A 108.2 . . ? C39 N31 C32 108.36(16) . . ? C39 N31 C30 125.22(17) . . ? C32 N31 C30 126.42(16) . . ? N31 C32 C37 106.51(18) . . ? N31 C32 C33 131.46(19) . . ? C37 C32 C33 122.0(2) . . ? C34 C33 C32 115.6(2) . . ? C34 C33 H33 122.2 . . ? C32 C33 H33 122.2 . . ? C33 C34 C35 122.3(2) . . ? C33 C34 H34 118.9 . . ? C35 C34 H34 118.9 . . ? C36 C35 C34 122.0(2) . . ? C36 C35 H35 119.0 . . ? C34 C35 H35 119.0 . . ? C35 C36 C37 116.1(2) . . ? C35 C36 H36 121.9 . . ? C37 C36 H36 121.9 . . ? N38 C37 C32 106.44(17) . . ? N38 C37 C36 131.6(2) . . ? C32 C37 C36 122.0(2) . . ? C39 N38 C37 108.93(17) . . ? C39 N38 H38 125.5 . . ? C37 N38 H38 125.5 . . ? N38 C39 N31 109.76(18) . . ? N38 C39 H39 125.1 . . ? N31 C39 H39 125.1 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C39 H39 Cl41 0.93 2.68 3.563(2) 158.2 1 C26 H26 Cl40 0.93 2.46 3.379(2) 171.7 1_565 C13 H13 Cl40 0.93 2.44 3.366(2) 171.3 1_565 N38 H38 Cl40 0.86 2.13 2.9800(17) 170.0 1_465 N25 H25 Cl43 0.86 2.27 3.1193(19) 168.9 1_655 N12 H12 Cl41 0.86 2.26 3.105(2) 169.2 1_655 _diffrn_measured_fraction_theta_max 0.842 _diffrn_reflns_theta_full 31.95 _diffrn_measured_fraction_theta_full 0.842 _refine_diff_density_max 1.796 _refine_diff_density_min -0.696 _refine_diff_density_rms 0.087 # Attachment 'TBIMNCL_0m.cif' data_tbimncl_0m _database_code_depnum_ccdc_archive 'CCDC 711821' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C66 H66 Cl2 N16 O20' _chemical_formula_weight 1474.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting MONOCLINIC _symmetry_space_group_name_H-M C2/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z' _cell_length_a 22.891(3) _cell_length_b 11.2053(12) _cell_length_c 13.5851(15) _cell_angle_alpha 90.00 _cell_angle_beta 100.816(3) _cell_angle_gamma 90.00 _cell_volume 3422.7(6) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.430 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1536 _exptl_absorpt_coefficient_mu 0.182 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9144 _exptl_absorpt_correction_T_max 0.9645 _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 'BRUKER CCD AREA DETECTOR' _diffrn_measurement_method 'PHI-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 18071 _diffrn_reflns_av_R_equivalents 0.0453 _diffrn_reflns_av_sigmaI/netI 0.0346 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.53 _diffrn_reflns_theta_max 26.45 _reflns_number_total 3698 _reflns_number_gt 2935 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER AXS SMART 3' _computing_cell_refinement 'BRUKER AXS SMART 3' _computing_data_reduction 'BRUKER AXS SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'BRUKER SHELXTL' _computing_publication_material 'MERCURY 1.4' _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^)+(0.1983P)^2^+19.5392P] 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 3698 _refine_ls_number_parameters 270 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1134 _refine_ls_R_factor_gt 0.0979 _refine_ls_wR_factor_ref 0.3115 _refine_ls_wR_factor_gt 0.2927 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.2023(2) 0.0000 0.1519(5) 0.0266(12) Uani 1 2 d S . . H1 H 0.1988 0.0000 0.0826 0.032 Uiso 1 2 calc SR . . N2 N 0.2532(2) 0.0000 0.2167(4) 0.0317(12) Uani 1 2 d S . . H2 H 0.2880 0.0000 0.2016 0.038 Uiso 1 2 calc SR . . C3 C 0.2414(3) 0.0000 0.3122(5) 0.0326(14) Uani 1 2 d S . . C4 C 0.2789(3) 0.0000 0.4059(5) 0.0399(17) Uani 1 2 d S . . H4 H 0.3201 0.0000 0.4128 0.048 Uiso 1 2 calc SR . . C5 C 0.2514(4) 0.0000 0.4870(5) 0.046(2) Uani 1 2 d S . . H5 H 0.2749 0.0000 0.5508 0.055 Uiso 1 2 calc SR . . C6 C 0.1896(4) 0.0000 0.4783(5) 0.0407(17) Uani 1 2 d S . . H6 H 0.1733 0.0000 0.5361 0.049 Uiso 1 2 calc SR . . C7 C 0.1521(3) 0.0000 0.3858(4) 0.0290(13) Uani 1 2 d S . . H7 H 0.1110 0.0000 0.3797 0.035 Uiso 1 2 calc SR . . C8 C 0.1790(3) 0.0000 0.3038(4) 0.0255(12) Uani 1 2 d S . . N9 N 0.15613(19) 0.0000 0.2011(3) 0.0210(10) Uani 1 2 d S . . C10 C 0.0919(2) 0.0000 0.1552(4) 0.0199(11) Uani 1 2 d S . . H10A H 0.0733 0.0699 0.1779 0.024 Uiso 0.50 1 calc PR . . H10B H 0.0733 -0.0699 0.1779 0.024 Uiso 0.50 1 calc PR . . C11 C 0.0810(2) 0.0000 0.0411(4) 0.0179(10) Uani 1 2 d S . . C12 C 0.07628(14) 0.1094(3) -0.0099(3) 0.0176(8) Uani 1 1 d . . . C13 C 0.08627(17) 0.2254(4) 0.0475(3) 0.0232(8) Uani 1 1 d . . . H13C H 0.0488 0.2566 0.0575 0.035 Uiso 1 1 calc R . . H13B H 0.1050 0.2819 0.0102 0.035 Uiso 1 1 calc R . . H13A H 0.1115 0.2115 0.1114 0.035 Uiso 1 1 calc R . . C14 C 0.06212(14) 0.1085(3) -0.1159(2) 0.0163(7) Uani 1 1 d . . . C15 C 0.05762(15) 0.2249(3) -0.1734(3) 0.0196(8) Uani 1 1 d . . . H15B H 0.0177 0.2333 -0.2121 0.023 Uiso 1 1 calc R . . H15A H 0.0647 0.2908 -0.1264 0.023 Uiso 1 1 calc R . . N16 N 0.10071(13) 0.2305(3) -0.2412(2) 0.0180(7) Uani 1 1 d . . . C17 C 0.16173(15) 0.2081(3) -0.2168(3) 0.0188(8) Uani 1 1 d . . . C18 C 0.19927(16) 0.1764(4) -0.1264(3) 0.0227(8) Uani 1 1 d . . . H18 H 0.1852 0.1683 -0.0669 0.027 Uiso 1 1 calc R . . C19 C 0.25858(17) 0.1580(4) -0.1312(3) 0.0278(9) Uani 1 1 d . . . H19 H 0.2849 0.1361 -0.0733 0.033 Uiso 1 1 calc R . . C20 C 0.28021(17) 0.1714(4) -0.2209(3) 0.0283(9) Uani 1 1 d . . . H20 H 0.3202 0.1570 -0.2207 0.034 Uiso 1 1 calc R . . C21 C 0.24378(18) 0.2053(4) -0.3089(3) 0.0272(9) Uani 1 1 d . . . H21 H 0.2583 0.2156 -0.3678 0.033 Uiso 1 1 calc R . . C22 C 0.18363(16) 0.2234(3) -0.3049(3) 0.0202(8) Uani 1 1 d . . . N23 N 0.13565(15) 0.2551(3) -0.3789(2) 0.0245(8) Uani 1 1 d . . . H23 H 0.1371 0.2702 -0.4404 0.029 Uiso 1 1 calc R . . C24 C 0.08721(17) 0.2580(3) -0.3383(3) 0.0219(8) Uani 1 1 d . . . H24 H 0.0493 0.2766 -0.3728 0.026 Uiso 1 1 calc R . . C25 C 0.0527(2) 0.0000 -0.1685(3) 0.0164(10) Uani 1 2 d S . . C26 C 0.0330(2) 0.0000 -0.2812(4) 0.0194(11) Uani 1 2 d S . . H26A H 0.060(3) 0.0000 -0.309(5) 0.030(19) Uiso 1 2 d S . . H26B H 0.0073(19) 0.069(4) -0.307(3) 0.019(10) Uiso 1 1 d . . . Cl27 Cl 0.35828(8) 0.0000 0.10545(16) 0.0477(5) Uani 1 2 d S . . O28 O 0.4782(4) 0.0000 0.0214(10) 0.129(4) Uani 1 2 d S . . N29 N 0.40873(14) 0.2377(3) 0.6226(2) 0.0238(7) Uani 1 1 d . . . O30 O 0.35984(12) 0.1986(3) 0.5737(2) 0.0316(7) Uani 1 1 d . . . O31 O 0.41632(14) 0.2444(4) 0.7150(2) 0.0409(9) Uani 1 1 d . . . O32 O 0.44807(13) 0.2693(3) 0.5760(2) 0.0354(8) Uani 1 1 d . . . O33 O 0.4316(3) 0.0000 0.8158(5) 0.0633(16) Uani 1 2 d S . . O34A O 0.4757(6) 0.0000 0.5146(10) 0.089(3) Uiso 0.68 2 d SP . . O34B O 0.4398(7) 0.0000 0.4730(11) 0.036(3) Uiso 0.32 2 d SP . . O35B O 0.5246(6) 0.0000 0.7041(10) 0.101(4) Uiso 0.71 2 d SP . . O35A O 0.4859(8) 0.0000 0.6202(14) 0.049(4) Uiso 0.29 2 d SP . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.016(3) 0.029(3) 0.034(3) 0.000 0.004(2) 0.000 N2 0.012(2) 0.030(3) 0.049(3) 0.000 -0.003(2) 0.000 C3 0.026(3) 0.019(3) 0.044(4) 0.000 -0.014(3) 0.000 C4 0.039(4) 0.022(3) 0.047(4) 0.000 -0.022(3) 0.000 C5 0.060(5) 0.025(3) 0.037(4) 0.000 -0.032(3) 0.000 C6 0.066(5) 0.027(3) 0.022(3) 0.000 -0.010(3) 0.000 C7 0.033(3) 0.028(3) 0.023(3) 0.000 -0.005(2) 0.000 C8 0.028(3) 0.022(3) 0.020(3) 0.000 -0.011(2) 0.000 N9 0.016(2) 0.027(2) 0.017(2) 0.000 -0.0029(17) 0.000 C10 0.015(2) 0.032(3) 0.012(2) 0.000 0.0010(18) 0.000 C11 0.011(2) 0.032(3) 0.011(2) 0.000 0.0024(17) 0.000 C12 0.0089(15) 0.0275(19) 0.0161(16) -0.0007(14) 0.0018(12) -0.0004(13) C13 0.0213(18) 0.031(2) 0.0173(17) -0.0055(15) 0.0034(14) -0.0035(15) C14 0.0102(15) 0.0247(19) 0.0144(16) 0.0007(13) 0.0033(12) -0.0007(13) C15 0.0150(16) 0.026(2) 0.0180(17) 0.0005(14) 0.0053(13) -0.0019(14) N16 0.0143(14) 0.0238(16) 0.0159(14) 0.0023(12) 0.0031(11) -0.0023(12) C17 0.0146(17) 0.0222(18) 0.0190(17) -0.0006(14) 0.0015(13) -0.0025(13) C18 0.0185(18) 0.028(2) 0.0197(18) 0.0014(15) 0.0001(14) -0.0035(15) C19 0.0175(18) 0.035(2) 0.028(2) 0.0015(17) -0.0024(15) -0.0019(16) C20 0.0138(17) 0.033(2) 0.038(2) -0.0064(18) 0.0033(15) -0.0021(15) C21 0.0247(19) 0.031(2) 0.029(2) -0.0076(17) 0.0115(16) -0.0081(16) C22 0.0201(18) 0.0237(18) 0.0162(17) -0.0024(14) 0.0020(13) -0.0048(14) N23 0.0244(17) 0.0350(19) 0.0147(15) 0.0008(13) 0.0054(12) -0.0058(14) C24 0.0190(18) 0.0264(19) 0.0192(18) 0.0045(15) 0.0007(14) -0.0029(15) C25 0.010(2) 0.027(3) 0.012(2) 0.000 0.0031(17) 0.000 C26 0.019(2) 0.025(3) 0.014(2) 0.000 0.002(2) 0.000 Cl27 0.0416(10) 0.0380(9) 0.0682(13) 0.000 0.0222(9) 0.000 O28 0.093(7) 0.135(9) 0.168(11) 0.000 0.046(7) 0.000 N29 0.0190(16) 0.0335(18) 0.0189(16) -0.0032(13) 0.0038(12) -0.0019(13) O30 0.0212(14) 0.0523(19) 0.0200(14) -0.0046(13) 0.0003(11) -0.0128(13) O31 0.0314(17) 0.073(2) 0.0178(15) -0.0126(15) 0.0030(12) -0.0101(16) O32 0.0204(14) 0.058(2) 0.0276(15) 0.0044(14) 0.0044(11) -0.0106(14) O33 0.082(4) 0.050(3) 0.054(3) 0.000 0.004(3) 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 C1 N2 1.321(7) . ? C1 N9 1.353(7) . ? C1 H1 0.9300 . ? N2 C3 1.374(9) . ? N2 H2 0.8600 . ? C3 C4 1.395(8) . ? C3 C8 1.413(8) . ? C4 C5 1.367(12) . ? C4 H4 0.9300 . ? C5 C6 1.397(11) . ? C5 H5 0.9300 . ? C6 C7 1.382(8) . ? C6 H6 0.9300 . ? C7 C8 1.370(9) . ? C7 H7 0.9300 . ? C8 N9 1.395(7) . ? N9 C10 1.486(6) . ? C10 C11 1.523(6) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.402(4) 6 ? C11 C12 1.402(4) . ? C12 C14 1.415(5) . ? C12 C13 1.511(5) . ? C13 H13C 0.9600 . ? C13 H13B 0.9600 . ? C13 H13A 0.9600 . ? C14 C25 1.407(4) . ? C14 C15 1.513(5) . ? C15 N16 1.473(4) . ? C15 H15B 0.9700 . ? C15 H15A 0.9700 . ? N16 C24 1.333(5) . ? N16 C17 1.396(5) . ? C17 C22 1.393(5) . ? C17 C18 1.406(5) . ? C18 C19 1.387(5) . ? C18 H18 0.9300 . ? C19 C20 1.406(6) . ? C19 H19 0.9300 . ? C20 C21 1.376(6) . ? C20 H20 0.9300 . ? C21 C22 1.403(5) . ? C21 H21 0.9300 . ? C22 N23 1.388(5) . ? N23 C24 1.328(5) . ? N23 H23 0.8600 . ? C24 H24 0.9300 . ? C25 C14 1.407(4) 6 ? C25 C26 1.512(7) . ? C26 H26A 0.78(8) . ? C26 H26B 0.99(4) . ? O28 O28 1.245(19) 5_655 ? N29 O31 1.237(4) . ? N29 O32 1.245(4) . ? N29 O30 1.267(4) . ? O34A O34B 0.906(16) . ? O34A O34A 1.25(2) 5_656 ? O35B O35A 1.31(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 C1 N9 110.1(5) . . ? N2 C1 H1 125.0 . . ? N9 C1 H1 125.0 . . ? C1 N2 C3 109.0(5) . . ? C1 N2 H2 125.5 . . ? C3 N2 H2 125.5 . . ? N2 C3 C4 131.8(6) . . ? N2 C3 C8 107.4(5) . . ? C4 C3 C8 120.9(7) . . ? C5 C4 C3 116.0(7) . . ? C5 C4 H4 122.0 . . ? C3 C4 H4 122.0 . . ? C4 C5 C6 122.9(6) . . ? C4 C5 H5 118.5 . . ? C6 C5 H5 118.5 . . ? C7 C6 C5 121.5(7) . . ? C7 C6 H6 119.2 . . ? C5 C6 H6 119.2 . . ? C8 C7 C6 116.3(6) . . ? C8 C7 H7 121.9 . . ? C6 C7 H7 121.9 . . ? C7 C8 N9 132.3(5) . . ? C7 C8 C3 122.4(5) . . ? N9 C8 C3 105.3(5) . . ? C1 N9 C8 108.3(5) . . ? C1 N9 C10 126.6(4) . . ? C8 N9 C10 125.2(5) . . ? N9 C10 C11 112.8(4) . . ? N9 C10 H10A 109.0 . . ? C11 C10 H10A 109.0 . . ? N9 C10 H10B 109.0 . . ? C11 C10 H10B 109.0 . . ? H10A C10 H10B 107.8 . . ? C12 C11 C12 121.9(4) 6 . ? C12 C11 C10 119.0(2) 6 . ? C12 C11 C10 119.0(2) . . ? C11 C12 C14 118.6(3) . . ? C11 C12 C13 120.5(3) . . ? C14 C12 C13 121.0(3) . . ? C12 C13 H13C 109.5 . . ? C12 C13 H13B 109.5 . . ? H13C C13 H13B 109.5 . . ? C12 C13 H13A 109.5 . . ? H13C C13 H13A 109.5 . . ? H13B C13 H13A 109.5 . . ? C25 C14 C12 120.5(3) . . ? C25 C14 C15 119.5(3) . . ? C12 C14 C15 120.0(3) . . ? N16 C15 C14 111.8(3) . . ? N16 C15 H15B 109.3 . . ? C14 C15 H15B 109.3 . . ? N16 C15 H15A 109.3 . . ? C14 C15 H15A 109.3 . . ? H15B C15 H15A 107.9 . . ? C24 N16 C17 108.2(3) . . ? C24 N16 C15 124.8(3) . . ? C17 N16 C15 127.0(3) . . ? C22 C17 N16 106.2(3) . . ? C22 C17 C18 121.5(3) . . ? N16 C17 C18 132.3(3) . . ? C19 C18 C17 116.1(3) . . ? C19 C18 H18 122.0 . . ? C17 C18 H18 122.0 . . ? C18 C19 C20 122.1(4) . . ? C18 C19 H19 118.9 . . ? C20 C19 H19 118.9 . . ? C21 C20 C19 121.8(4) . . ? C21 C20 H20 119.1 . . ? C19 C20 H20 119.1 . . ? C20 C21 C22 116.5(4) . . ? C20 C21 H21 121.8 . . ? C22 C21 H21 121.8 . . ? N23 C22 C17 106.9(3) . . ? N23 C22 C21 131.2(4) . . ? C17 C22 C21 122.0(3) . . ? C24 N23 C22 108.4(3) . . ? C24 N23 H23 125.8 . . ? C22 N23 H23 125.8 . . ? N23 C24 N16 110.4(3) . . ? N23 C24 H24 124.8 . . ? N16 C24 H24 124.8 . . ? C14 C25 C14 119.6(4) . 6 ? C14 C25 C26 120.2(2) . . ? C14 C25 C26 120.2(2) 6 . ? C25 C26 H26A 112(5) . . ? C25 C26 H26B 113(2) . . ? H26A C26 H26B 108(4) . . ? O31 N29 O32 121.4(3) . . ? O31 N29 O30 119.6(3) . . ? O32 N29 O30 119.0(3) . . ? O34B O34A O34A 124(2) . 5_656 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 Cl27 0.86 2.25 3.072(6) 158.9 1 N23 H23 O30 0.86 1.86 2.719(4) 179.5 7 N23 H23 O32 0.86 2.46 2.999(4) 121.6 7 C10 H10A O31 0.97 2.52 3.388(4) 148.2 7_556 C10 H10B O31 0.97 2.52 3.388(4) 148.2 4_546 C15 H15B O31 0.97 2.36 3.323(5) 172.1 8_454 C24 H24 O32 0.93 2.35 3.194(5) 151.3 8_454 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.45 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 2.744 _refine_diff_density_min -1.060 _refine_diff_density_rms 0.134 # Attachment 'complex1_FINAL_R1.cif' data_complex1 _database_code_depnum_ccdc_archive 'CCDC 711822' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H35 N9 O10' _chemical_formula_weight 717.70 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting MONOCLINIC _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.0912(15) _cell_length_b 15.0534(19) _cell_length_c 19.735(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.931(2) _cell_angle_gamma 90.00 _cell_volume 3591.6(8) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2294 _cell_measurement_theta_min 0.961 _cell_measurement_theta_max 0.988 _exptl_crystal_description BLOCK _exptl_crystal_colour COLORLESS _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.327 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1504 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9609 _exptl_absorpt_correction_T_max 0.9880 _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 'BRUKER 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 27000 _diffrn_reflns_av_R_equivalents 0.0323 _diffrn_reflns_av_sigmaI/netI 0.0229 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 22.54 _reflns_number_total 4692 _reflns_number_gt 3777 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER AXS SMART 2' _computing_cell_refinement 'BRUKER AXS SMART 2' _computing_data_reduction 'BRUKER AXS SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'BRUKER SHELXTL' _computing_publication_material 'MERCURY 1.4' _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^)+(0.1591P)^2^+5.6718P] 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 4692 _refine_ls_number_parameters 474 _refine_ls_number_restraints 14 _refine_ls_R_factor_all 0.1016 _refine_ls_R_factor_gt 0.0880 _refine_ls_wR_factor_ref 0.2688 _refine_ls_wR_factor_gt 0.2537 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.072 _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 C1 C 0.7303(4) 0.6681(3) 0.0568(3) 0.0572(13) Uani 1 1 d . . . H1A H 0.7603 0.6921 0.0159 0.086 Uiso 1 1 calc R . . H1B H 0.6612 0.6393 0.0466 0.086 Uiso 1 1 calc R . . H1C H 0.7813 0.6258 0.0760 0.086 Uiso 1 1 calc R . . C2 C 0.7119(4) 0.7420(3) 0.1066(2) 0.0410(10) Uani 1 1 d . . . C3 C 0.6275(3) 0.8039(3) 0.0948(2) 0.0416(10) Uani 1 1 d . . . C4 C 0.5548(4) 0.7934(3) 0.0320(2) 0.0540(12) Uani 1 1 d . . . H4A H 0.5419 0.7307 0.0237 0.065 Uiso 1 1 calc R . . H4B H 0.4839 0.8214 0.0396 0.065 Uiso 1 1 calc R . . N5 N 0.6057(3) 0.8332(3) -0.02770(18) 0.0475(10) Uani 1 1 d . . . C6 C 0.5766(3) 0.8148(3) -0.0949(2) 0.0452(11) Uani 1 1 d . . . C7 C 0.4979(4) 0.7559(4) -0.1214(3) 0.0600(14) Uani 1 1 d . . . H7 H 0.4535 0.7207 -0.0943 0.072 Uiso 1 1 calc R . . C8 C 0.4916(5) 0.7543(4) -0.1916(3) 0.0735(17) Uani 1 1 d . . . H8 H 0.4411 0.7162 -0.2126 0.088 Uiso 1 1 calc R . . C9 C 0.5565(5) 0.8063(5) -0.2311(3) 0.0764(18) Uani 1 1 d . . . H9 H 0.5487 0.8016 -0.2779 0.092 Uiso 1 1 calc R . . C10 C 0.6332(4) 0.8658(4) -0.2050(3) 0.0634(14) Uani 1 1 d . . . H10 H 0.6762 0.9017 -0.2324 0.076 Uiso 1 1 calc R . . C11 C 0.6410(4) 0.8677(3) -0.1347(2) 0.0494(12) Uani 1 1 d . . . N12 N 0.7065(3) 0.9173(3) -0.09149(19) 0.0544(11) Uani 1 1 d . . . H12 H 0.7545 0.9563 -0.1034 0.065 Uiso 1 1 calc R . . C13 C 0.6833(4) 0.8950(3) -0.0287(2) 0.0536(12) Uani 1 1 d . . . H13 H 0.7170 0.9194 0.0097 0.064 Uiso 1 1 calc R . . C14 C 0.6104(4) 0.8730(3) 0.1400(2) 0.0460(11) Uani 1 1 d . . . C15 C 0.5199(4) 0.9414(3) 0.1272(3) 0.0706(16) Uani 1 1 d . . . H15A H 0.4562 0.9264 0.1532 0.106 Uiso 1 1 calc R . . H15B H 0.5002 0.9418 0.0799 0.106 Uiso 1 1 calc R . . H15C H 0.5462 0.9991 0.1404 0.106 Uiso 1 1 calc R . . C16 C 0.6782(4) 0.8795(3) 0.1977(2) 0.0503(12) Uani 1 1 d . . . C17 C 0.6584(5) 0.9531(4) 0.2482(3) 0.0719(17) Uani 1 1 d . . . H17A H 0.5803 0.9679 0.2479 0.086 Uiso 1 1 calc R . . H17B H 0.6783 0.9322 0.2933 0.086 Uiso 1 1 calc R . . N18 N 0.7222(4) 1.0328(3) 0.2333(2) 0.0590(11) Uani 1 1 d . . . C19 C 0.7902(6) 1.0472(4) 0.1815(3) 0.0802(18) Uani 1 1 d . . . H19 H 0.8078 1.0056 0.1485 0.096 Uiso 1 1 calc R . . N20 N 0.8281(5) 1.1289(4) 0.1842(3) 0.0884(17) Uani 1 1 d . . . H20 H 0.8724 1.1523 0.1556 0.106 Uiso 1 1 calc R . . C21 C 0.7858(5) 1.1713(4) 0.2400(3) 0.0745(17) Uani 1 1 d . . . C22 C 0.7998(7) 1.2567(4) 0.2638(5) 0.100(3) Uani 1 1 d . . . H22 H 0.8454 1.2973 0.2424 0.120 Uiso 1 1 calc R . . C23 C 0.7437(9) 1.2775(6) 0.3193(8) 0.140(5) Uani 1 1 d . . . H23 H 0.7501 1.3347 0.3367 0.168 Uiso 1 1 calc R . . C24 C 0.6752(7) 1.2162(7) 0.3529(5) 0.119(3) Uani 1 1 d . . . H24 H 0.6387 1.2343 0.3917 0.143 Uiso 1 1 calc R . . C25 C 0.6607(5) 1.1300(4) 0.3298(3) 0.0740(17) Uani 1 1 d . . . H25 H 0.6162 1.0888 0.3515 0.089 Uiso 1 1 calc R . . C26 C 0.7185(5) 1.1108(3) 0.2713(3) 0.0612(14) Uani 1 1 d . . . C27 C 0.7638(4) 0.8195(3) 0.2100(2) 0.0495(12) Uani 1 1 d . . . C28 C 0.8363(5) 0.8278(5) 0.2729(3) 0.0794(18) Uani 1 1 d . . . H28A H 0.8560 0.8890 0.2797 0.119 Uiso 1 1 calc R . . H28B H 0.9021 0.7931 0.2675 0.119 Uiso 1 1 calc R . . H28C H 0.7967 0.8067 0.3115 0.119 Uiso 1 1 calc R . . C29 C 0.7801(4) 0.7497(3) 0.1646(2) 0.0430(11) Uani 1 1 d . . . C30 C 0.8676(4) 0.6805(4) 0.1779(3) 0.0647(14) Uani 1 1 d . . . H30A H 0.8948 0.6858 0.2242 0.078 Uiso 1 1 calc R . . H30B H 0.8356 0.6218 0.1723 0.078 Uiso 1 1 calc R . . N31 N 0.9609(3) 0.6910(3) 0.1308(2) 0.0539(10) Uani 1 1 d . . . C32 C 0.9937(4) 0.7667(4) 0.1028(3) 0.0611(14) Uani 1 1 d . . . H32 H 0.9641 0.8223 0.1120 0.073 Uiso 1 1 calc R . . N33 N 1.0746(3) 0.7513(3) 0.0601(2) 0.0624(12) Uani 1 1 d . . . H33 H 1.1080 0.7907 0.0365 0.075 Uiso 1 1 calc R . . C34 C 1.0964(4) 0.6603(4) 0.0597(3) 0.0584(13) Uani 1 1 d . . . C35 C 1.1714(5) 0.6114(4) 0.0238(3) 0.0713(15) Uani 1 1 d . . . H35 H 1.2194 0.6372 -0.0069 0.086 Uiso 1 1 calc R . . C36 C 1.1706(5) 0.5209(4) 0.0366(3) 0.0771(17) Uani 1 1 d . . . H36 H 1.2208 0.4852 0.0140 0.093 Uiso 1 1 calc R . . C37 C 1.0992(5) 0.4810(4) 0.0811(3) 0.0728(17) Uani 1 1 d . . . H37 H 1.1016 0.4198 0.0872 0.087 Uiso 1 1 calc R . . C38 C 1.0237(4) 0.5313(4) 0.1170(3) 0.0617(14) Uani 1 1 d . . . H38 H 0.9754 0.5055 0.1474 0.074 Uiso 1 1 calc R . . C39 C 1.0242(4) 0.6218(3) 0.1051(2) 0.0538(13) Uani 1 1 d . . . N40 N 0.7308(3) 0.1293(3) 0.0209(2) 0.0557(11) Uani 1 1 d . . . O41 O 0.6675(3) 0.0735(3) 0.0426(2) 0.0821(12) Uani 1 1 d . . . O42 O 0.7027(3) 0.2050(3) 0.0093(2) 0.0862(13) Uani 1 1 d . . . O43A O 0.8410(5) 0.1182(4) 0.0226(3) 0.0564(14) Uiso 0.64 1 d P . . O43B O 0.8052(9) 0.0933(7) -0.0081(5) 0.059(2) Uiso 0.36 1 d P . . N44 N 0.0329(6) 0.2233(4) 0.0959(4) 0.286(10) Uani 1 1 d D . . O45A O -0.0547(6) 0.2695(5) 0.1205(4) 0.069(2) Uiso 0.50 1 d PD . . O45B O -0.027(5) 0.290(3) 0.100(2) 0.59(5) Uiso 0.50 1 d PD . . O46A O 0.1173(8) 0.2515(7) 0.0647(5) 0.112(4) Uiso 0.57 1 d PD . . O46B O 0.1062(9) 0.2155(9) 0.0507(5) 0.078(3) Uiso 0.43 1 d PD . . O47B O 0.043(2) 0.1695(18) 0.1445(11) 0.260(13) Uiso 0.39 1 d PD . . O47A O 0.0124(8) 0.1387(5) 0.0798(5) 0.127(3) Uiso 0.61 1 d PD . . N48A N 0.0704(9) 0.0073(8) 0.1738(5) 0.072(3) Uiso 0.48 1 d P . . N48B N 0.1065(9) -0.0362(7) 0.1832(5) 0.073(3) Uiso 0.52 1 d P . . O49A O 0.0768(8) 0.0936(6) 0.1739(5) 0.094(2) Uiso 0.52 1 d P . . O49B O 0.1800(9) -0.0061(7) 0.2211(5) 0.097(3) Uiso 0.48 1 d P . . O50 O 0.1261(4) -0.0346(3) 0.1253(2) 0.0810(12) Uani 1 1 d . . . O51 O 0.0125(5) -0.0519(4) 0.2064(3) 0.129(2) Uani 1 1 d . . . O52 O 0.9088(3) 0.9442(2) 0.0472(2) 0.0665(10) Uani 1 1 d D . . H52A H 0.895(6) 0.997(3) 0.029(3) 0.11(2) Uiso 1 1 d D . . H52B H 0.965(4) 0.951(5) 0.076(3) 0.12(3) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.056(3) 0.049(3) 0.067(3) -0.011(2) 0.012(2) -0.007(2) C2 0.045(3) 0.034(2) 0.044(2) 0.0016(18) 0.008(2) -0.0054(19) C3 0.034(2) 0.044(3) 0.047(3) 0.004(2) 0.0021(19) -0.006(2) C4 0.046(3) 0.061(3) 0.055(3) 0.007(2) -0.001(2) -0.008(2) N5 0.044(2) 0.051(2) 0.047(2) 0.0025(17) -0.0065(17) -0.0031(18) C6 0.035(2) 0.050(3) 0.050(3) -0.006(2) -0.001(2) 0.010(2) C7 0.046(3) 0.071(3) 0.063(3) -0.020(3) 0.002(2) 0.010(2) C8 0.049(3) 0.105(5) 0.066(4) -0.035(3) 0.000(3) 0.009(3) C9 0.066(4) 0.112(5) 0.052(3) -0.021(3) -0.001(3) 0.027(4) C10 0.058(3) 0.083(4) 0.050(3) -0.006(3) 0.005(2) 0.021(3) C11 0.047(3) 0.052(3) 0.049(3) -0.001(2) -0.004(2) 0.017(2) N12 0.063(3) 0.051(2) 0.049(2) 0.0101(19) 0.004(2) 0.000(2) C13 0.059(3) 0.055(3) 0.046(3) 0.006(2) -0.004(2) -0.003(3) C14 0.037(2) 0.037(2) 0.065(3) 0.006(2) 0.014(2) 0.0015(19) C15 0.048(3) 0.049(3) 0.115(5) 0.006(3) 0.019(3) 0.007(2) C16 0.054(3) 0.046(3) 0.052(3) -0.009(2) 0.018(2) -0.008(2) C17 0.089(4) 0.056(3) 0.071(4) -0.021(3) 0.037(3) -0.016(3) N18 0.077(3) 0.049(2) 0.051(2) -0.0115(19) 0.011(2) -0.013(2) C19 0.095(4) 0.078(4) 0.068(4) -0.017(3) 0.026(3) -0.033(4) N20 0.104(4) 0.088(4) 0.073(3) 0.004(3) -0.005(3) -0.051(3) C21 0.083(4) 0.054(3) 0.086(4) -0.004(3) -0.033(3) -0.005(3) C22 0.092(5) 0.052(4) 0.154(7) -0.014(4) -0.063(5) 0.003(4) C23 0.098(7) 0.081(6) 0.238(13) -0.082(7) -0.097(8) 0.034(5) C24 0.094(6) 0.126(7) 0.135(7) -0.090(6) -0.050(5) 0.042(5) C25 0.072(4) 0.079(4) 0.070(4) -0.033(3) -0.021(3) 0.023(3) C26 0.069(3) 0.050(3) 0.065(3) -0.015(3) -0.017(3) 0.007(3) C27 0.048(3) 0.057(3) 0.044(3) 0.004(2) 0.005(2) -0.015(2) C28 0.088(4) 0.097(5) 0.053(3) -0.001(3) -0.013(3) -0.028(4) C29 0.043(3) 0.043(2) 0.043(2) 0.007(2) 0.005(2) -0.0008(19) C30 0.059(3) 0.072(3) 0.063(3) 0.025(3) 0.008(3) 0.013(3) N31 0.045(2) 0.058(3) 0.059(2) 0.015(2) -0.0020(19) 0.010(2) C32 0.041(3) 0.065(3) 0.078(4) 0.014(3) 0.009(3) 0.018(2) N33 0.045(2) 0.064(3) 0.079(3) 0.009(2) 0.010(2) 0.009(2) C34 0.046(3) 0.062(3) 0.067(3) -0.008(3) -0.002(3) 0.011(2) C35 0.061(3) 0.071(4) 0.082(4) -0.014(3) 0.003(3) 0.007(3) C36 0.071(4) 0.066(4) 0.094(4) -0.026(3) -0.010(3) 0.013(3) C37 0.077(4) 0.054(3) 0.086(4) -0.010(3) -0.028(3) 0.007(3) C38 0.054(3) 0.059(3) 0.071(3) 0.005(3) -0.018(3) 0.003(3) C39 0.042(3) 0.059(3) 0.059(3) 0.003(2) -0.013(2) 0.010(2) N40 0.048(2) 0.061(3) 0.058(2) 0.001(2) 0.0024(19) 0.014(2) O41 0.064(2) 0.052(2) 0.130(4) 0.005(2) 0.000(2) -0.005(2) O42 0.063(2) 0.066(3) 0.130(4) 0.026(2) 0.008(2) 0.016(2) N44 0.260(13) 0.226(11) 0.364(17) 0.243(12) -0.230(13) -0.225(11) O50 0.099(3) 0.063(2) 0.082(3) 0.008(2) 0.028(2) 0.008(2) O51 0.123(4) 0.168(6) 0.096(4) 0.020(4) 0.040(3) -0.031(4) O52 0.065(2) 0.049(2) 0.086(3) 0.0170(19) 0.000(2) -0.0052(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.503(6) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.399(6) . ? C2 C29 1.406(6) . ? C3 C14 1.388(6) . ? C3 C4 1.516(6) . ? C4 N5 1.466(6) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? N5 C13 1.321(6) . ? N5 C6 1.394(6) . ? C6 C11 1.370(7) . ? C6 C7 1.396(7) . ? C7 C8 1.386(8) . ? C7 H7 0.9300 . ? C8 C9 1.362(9) . ? C8 H8 0.9300 . ? C9 C10 1.382(8) . ? C9 H9 0.9300 . ? C10 C11 1.390(7) . ? C10 H10 0.9300 . ? C11 N12 1.375(6) . ? N12 C13 1.318(6) . ? N12 H12 0.8600 . ? C13 H13 0.9300 . ? C14 C16 1.395(7) . ? C14 C15 1.521(7) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 C27 1.393(7) . ? C16 C17 1.512(7) . ? C17 N18 1.460(6) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? N18 C19 1.340(7) . ? N18 C26 1.394(6) . ? C19 N20 1.314(7) . ? C19 H19 0.9300 . ? N20 C21 1.379(8) . ? N20 H20 0.8600 . ? C21 C26 1.374(8) . ? C21 C22 1.377(9) . ? C22 C23 1.336(14) . ? C22 H22 0.9300 . ? C23 C24 1.412(15) . ? C23 H23 0.9300 . ? C24 C25 1.385(10) . ? C24 H24 0.9300 . ? C25 C26 1.390(8) . ? C25 H25 0.9300 . ? C27 C29 1.395(6) . ? C27 C28 1.514(7) . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 C30 1.505(7) . ? C30 N31 1.482(6) . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? N31 C32 1.329(7) . ? N31 C39 1.393(6) . ? C32 N33 1.322(6) . ? C32 H32 0.9300 . ? N33 C34 1.394(7) . ? N33 H33 0.8600 . ? C34 C35 1.374(7) . ? C34 C39 1.390(7) . ? C35 C36 1.385(9) . ? C35 H35 0.9300 . ? C36 C37 1.379(9) . ? C36 H36 0.9300 . ? C37 C38 1.388(8) . ? C37 H37 0.9300 . ? C38 C39 1.381(7) . ? C38 H38 0.9300 . ? N40 O43B 1.203(10) . ? N40 O42 1.211(5) . ? N40 O41 1.218(5) . ? N40 O43A 1.343(7) . ? O43A O43B 0.828(9) . ? N44 O45B 1.240(11) . ? N44 O47B 1.258(11) . ? N44 O46A 1.273(8) . ? N44 O46B 1.273(9) . ? N44 O47A 1.335(8) . ? N44 O45A 1.363(8) . ? O45A O45B 0.61(4) . ? O46A O46B 0.623(14) . ? O47B O47A 1.40(3) . ? N48A N48B 0.808(12) . ? N48A O49A 1.301(14) . ? N48A O51 1.309(12) . ? N48A O50 1.338(12) . ? N48A O49B 1.621(15) . ? N48B O50 1.171(10) . ? N48B O49B 1.238(13) . ? N48B O51 1.255(11) . ? O52 H52A 0.89(2) . ? O52 H52B 0.88(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 C2 C29 119.8(4) . . ? C3 C2 C1 120.0(4) . . ? C29 C2 C1 120.2(4) . . ? C14 C3 C2 120.5(4) . . ? C14 C3 C4 120.9(4) . . ? C2 C3 C4 118.5(4) . . ? N5 C4 C3 111.7(4) . . ? N5 C4 H4A 109.3 . . ? C3 C4 H4A 109.3 . . ? N5 C4 H4B 109.3 . . ? C3 C4 H4B 109.3 . . ? H4A C4 H4B 107.9 . . ? C13 N5 C6 107.1(4) . . ? C13 N5 C4 127.4(4) . . ? C6 N5 C4 125.4(4) . . ? C11 C6 N5 107.0(4) . . ? C11 C6 C7 123.0(4) . . ? N5 C6 C7 130.1(4) . . ? C8 C7 C6 114.4(5) . . ? C8 C7 H7 122.8 . . ? C6 C7 H7 122.8 . . ? C9 C8 C7 122.6(5) . . ? C9 C8 H8 118.7 . . ? C7 C8 H8 118.7 . . ? C8 C9 C10 123.3(5) . . ? C8 C9 H9 118.4 . . ? C10 C9 H9 118.4 . . ? C9 C10 C11 114.8(5) . . ? C9 C10 H10 122.6 . . ? C11 C10 H10 122.6 . . ? C6 C11 N12 106.7(4) . . ? C6 C11 C10 122.0(5) . . ? N12 C11 C10 131.2(5) . . ? C13 N12 C11 108.3(4) . . ? C13 N12 H12 125.8 . . ? C11 N12 H12 125.8 . . ? N12 C13 N5 110.8(4) . . ? N12 C13 H13 124.6 . . ? N5 C13 H13 124.6 . . ? C3 C14 C16 119.1(4) . . ? C3 C14 C15 120.9(5) . . ? C16 C14 C15 120.0(4) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C27 C16 C14 121.4(4) . . ? C27 C16 C17 119.1(5) . . ? C14 C16 C17 119.5(5) . . ? N18 C17 C16 112.3(4) . . ? N18 C17 H17A 109.1 . . ? C16 C17 H17A 109.1 . . ? N18 C17 H17B 109.1 . . ? C16 C17 H17B 109.1 . . ? H17A C17 H17B 107.9 . . ? C19 N18 C26 107.5(4) . . ? C19 N18 C17 128.2(4) . . ? C26 N18 C17 124.2(4) . . ? N20 C19 N18 109.7(5) . . ? N20 C19 H19 125.2 . . ? N18 C19 H19 125.2 . . ? C19 N20 C21 109.4(5) . . ? C19 N20 H20 125.3 . . ? C21 N20 H20 125.3 . . ? C26 C21 C22 122.4(8) . . ? C26 C21 N20 106.4(5) . . ? C22 C21 N20 131.2(7) . . ? C23 C22 C21 115.9(9) . . ? C23 C22 H22 122.0 . . ? C21 C22 H22 122.0 . . ? C22 C23 C24 122.8(7) . . ? C22 C23 H23 118.6 . . ? C24 C23 H23 118.6 . . ? C25 C24 C23 122.0(8) . . ? C25 C24 H24 119.0 . . ? C23 C24 H24 119.0 . . ? C24 C25 C26 113.9(8) . . ? C24 C25 H25 123.0 . . ? C26 C25 H25 123.0 . . ? C21 C26 C25 123.0(5) . . ? C21 C26 N18 107.0(5) . . ? C25 C26 N18 130.0(5) . . ? C16 C27 C29 119.3(4) . . ? C16 C27 C28 120.5(5) . . ? C29 C27 C28 120.2(5) . . ? 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 . . ? C27 C29 C2 119.9(4) . . ? C27 C29 C30 121.1(4) . . ? C2 C29 C30 119.0(4) . . ? N31 C30 C29 110.9(4) . . ? N31 C30 H30A 109.5 . . ? C29 C30 H30A 109.5 . . ? N31 C30 H30B 109.5 . . ? C29 C30 H30B 109.5 . . ? H30A C30 H30B 108.0 . . ? C32 N31 C39 108.8(4) . . ? C32 N31 C30 125.9(4) . . ? C39 N31 C30 125.2(4) . . ? N33 C32 N31 110.1(5) . . ? N33 C32 H32 125.0 . . ? N31 C32 H32 125.0 . . ? C32 N33 C34 108.6(4) . . ? C32 N33 H33 125.7 . . ? C34 N33 H33 125.7 . . ? C35 C34 C39 122.4(5) . . ? C35 C34 N33 131.1(5) . . ? C39 C34 N33 106.6(4) . . ? C34 C35 C36 115.3(6) . . ? C34 C35 H35 122.4 . . ? C36 C35 H35 122.4 . . ? C37 C36 C35 123.4(6) . . ? C37 C36 H36 118.3 . . ? C35 C36 H36 118.3 . . ? C36 C37 C38 120.7(5) . . ? C36 C37 H37 119.6 . . ? C38 C37 H37 119.6 . . ? C39 C38 C37 116.5(5) . . ? C39 C38 H38 121.7 . . ? C37 C38 H38 121.7 . . ? C38 C39 C34 121.7(5) . . ? C38 C39 N31 132.2(5) . . ? C34 C39 N31 106.1(4) . . ? O43B N40 O42 122.9(6) . . ? O43B N40 O41 109.6(6) . . ? O42 N40 O41 122.7(4) . . ? O43B N40 O43A 37.5(5) . . ? O42 N40 O43A 113.4(5) . . ? O41 N40 O43A 122.3(4) . . ? O43B O43A N40 62.0(8) . . ? O43A O43B N40 80.5(10) . . ? O45B N44 O47B 120.9(13) . . ? O45B N44 O46A 104(2) . . ? O47B N44 O46A 121.2(15) . . ? O45B N44 O46B 122.5(13) . . ? O47B N44 O46B 114.6(11) . . ? O46A N44 O46B 28.3(6) . . ? O45B N44 O47A 133(4) . . ? O47B N44 O47A 65.4(15) . . ? O46A N44 O47A 110.5(9) . . ? O46B N44 O47A 82.7(9) . . ? O45B N44 O45A 26.6(19) . . ? O47B N44 O45A 96.9(12) . . ? O46A N44 O45A 129.4(8) . . ? O46B N44 O45A 148.3(9) . . ? O47A N44 O45A 115.4(6) . . ? O45B O45A N44 65.4(12) . . ? O45A O45B N44 88(2) . . ? O46B O46A N44 75.8(11) . . ? O46A O46B N44 75.9(11) . . ? N44 O47B O47A 60.0(10) . . ? N44 O47A O47B 54.7(8) . . ? N48B N48A O49A 141.0(16) . . ? N48B N48A O51 68.1(12) . . ? O49A N48A O51 135.3(11) . . ? N48B N48A O50 60.3(11) . . ? O49A N48A O50 116.2(9) . . ? O51 N48A O50 108.1(9) . . ? N48B N48A O49B 48.1(10) . . ? O49A N48A O49B 94.3(8) . . ? O51 N48A O49B 94.1(8) . . ? O50 N48A O49B 86.4(8) . . ? N48A N48B O50 82.9(13) . . ? N48A N48B O49B 102.8(14) . . ? O50 N48B O49B 115.3(10) . . ? N48A N48B O51 75.3(12) . . ? O50 N48B O51 124.0(9) . . ? O49B N48B O51 119.6(10) . . ? N48B O49B N48A 29.1(6) . . ? N48B O50 N48A 36.8(6) . . ? N48B O51 N48A 36.6(6) . . ? H52A O52 H52B 108(7) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N12 H12 O50 0.86 1.92 2.775(6) 173.5 3_665 N12 H12 O49A 0.86 2.60 3.110(10) 119.2 3_665 N12 H12 O49B 0.86 2.58 3.213(11) 131.5 3_665 N20 H20 O45A 0.86 2.09 2.850(10) 146.3 1_665 N20 H20 O45B 0.86 2.65 3.43(5) 152.5 1_665 N20 H20 O49A 0.86 2.64 3.064(11) 111.4 1_665 N20 H20 O47A 0.86 2.29 3.063(11) 150.2 1_665 N20 H20 O47B 0.86 2.09 2.79(3) 138.2 1_665 N33 H33 O43A 0.86 1.91 2.761(7) 170.5 3_765 N33 H33 O43B 0.86 2.12 2.948(11) 162.3 3_765 N33 H33 O42 0.86 2.47 3.111(6) 131.4 3_765 O52 H52A O43A 0.89(2) 1.94(3) 2.785(6) 158(7) 1_565 O52 H52A O43B 0.89(2) 1.95(4) 2.785(10) 157(7) 1_565 O52 H52B O50 0.88(2) 2.18(3) 3.042(6) 166(7) 1_665 O52 H52B O51 0.88(2) 2.63(5) 3.364(7) 142(7) 1_665 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 22.54 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.191 _refine_diff_density_min -0.542 _refine_diff_density_rms 0.062