# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'De-Xian Wang' _publ_contact_author_email dxwang@iccas.ac.cn _publ_author_name 'De-Xian Wang' # Attachment '5a.pdf' # Attachment '5b.cif' data_a _database_code_depnum_ccdc_archive 'CCDC 897874' #TrackingRef '5b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H8 F10 N6 O6' _chemical_formula_sum 'C30 H8 F10 N6 O6' _chemical_formula_weight 738.42 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.587(3) _cell_length_b 18.349(4) _cell_length_c 13.403(3) _cell_angle_alpha 90.00 _cell_angle_beta 106.57(3) _cell_angle_gamma 90.00 _cell_volume 2967.0(10) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 8000 _cell_measurement_theta_min 1.5852 _cell_measurement_theta_max 27.5367 _exptl_crystal_description block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.653 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1472 _exptl_absorpt_coefficient_mu 0.159 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7400 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'CrystalClear (Rigaku Inc., 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Saturn724+ CCD' _diffrn_measurement_method '\w scans at fixed \c = 45\%' _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23943 _diffrn_reflns_av_R_equivalents 0.0622 _diffrn_reflns_av_sigmaI/netI 0.0595 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 27.49 _reflns_number_total 6787 _reflns_number_gt 5576 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; Mercury: visualization and analysis of crystal structures, C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor, M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006. ; _computing_publication_material 'SHELX-97 (Sheldrick, 1997)' _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^)+(0.0996P)^2^+3.5432P] 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 6787 _refine_ls_number_parameters 469 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1540 _refine_ls_R_factor_gt 0.1296 _refine_ls_wR_factor_ref 0.3110 _refine_ls_wR_factor_gt 0.2943 _refine_ls_goodness_of_fit_ref 1.386 _refine_ls_restrained_S_all 1.386 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.001 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 F1 F 0.9758(3) 0.1979(2) 0.2956(3) 0.0612(9) Uani 1 1 d . . . F2 F 1.1679(3) 0.1413(2) 0.4174(3) 0.0681(10) Uani 1 1 d . . . F3 F 1.2813(3) 0.2112(2) 0.5952(3) 0.0663(10) Uani 1 1 d . . . F4 F 1.1975(3) 0.3336(2) 0.6544(3) 0.0639(10) Uani 1 1 d . . . F5 F 1.0050(3) 0.39177(19) 0.5321(3) 0.0624(10) Uani 1 1 d . . . F6 F -0.0286(4) -0.0494(3) -0.1180(5) 0.1105(19) Uani 1 1 d . . . F7 F -0.1443(4) 0.0016(3) -0.3064(5) 0.141(3) Uani 1 1 d . . . F8 F -0.0354(6) 0.0507(3) -0.4408(4) 0.143(3) Uani 1 1 d . . . F9 F 0.1892(5) 0.0456(3) -0.3877(3) 0.1050(18) Uani 1 1 d . . . F10 F 0.3041(3) -0.0028(2) -0.1956(3) 0.0645(10) Uani 1 1 d . . . O1 O 0.8920(3) 0.3274(2) 0.3481(3) 0.0498(9) Uani 1 1 d . . . O2 O 0.6989(3) 0.1437(2) 0.4394(3) 0.0517(10) Uani 1 1 d . . . O3 O 0.3981(3) -0.01418(19) 0.2685(3) 0.0499(10) Uani 1 1 d . . . O4 O 0.5221(3) 0.33277(19) 0.2374(3) 0.0470(9) Uani 1 1 d . . . O5 O 0.2212(3) 0.17554(19) 0.0664(3) 0.0434(9) Uani 1 1 d . . . O6 O 0.1982(4) -0.0558(2) -0.0603(3) 0.0557(11) Uani 1 1 d . . . N1 N 0.7993(4) 0.2327(2) 0.3973(3) 0.0415(10) Uani 1 1 d . . . N2 N 0.6018(3) 0.2357(2) 0.3380(3) 0.0408(10) Uani 1 1 d . . . N3 N 0.7075(4) 0.3304(2) 0.2893(3) 0.0417(10) Uani 1 1 d . . . N4 N 0.3143(3) 0.0842(2) 0.1726(3) 0.0398(10) Uani 1 1 d . . . N5 N 0.2985(4) -0.0365(2) 0.1051(4) 0.0478(11) Uani 1 1 d . . . N6 N 0.2067(4) 0.0628(2) -0.0011(3) 0.0405(10) Uani 1 1 d . . . C1 C 1.0306(5) 0.2319(3) 0.3834(4) 0.0487(13) Uani 1 1 d . . . C2 C 1.1285(5) 0.2029(3) 0.4458(5) 0.0521(14) Uani 1 1 d . . . C3 C 1.1857(5) 0.2382(3) 0.5353(5) 0.0492(14) Uani 1 1 d . . . C4 C 1.1448(5) 0.3009(3) 0.5647(4) 0.0499(14) Uani 1 1 d . . . C5 C 1.0459(5) 0.3299(3) 0.5024(5) 0.0490(14) Uani 1 1 d . . . C6 C 0.9876(4) 0.2958(3) 0.4109(4) 0.0440(12) Uani 1 1 d . . . C7 C 0.7931(4) 0.2941(3) 0.3449(4) 0.0389(11) Uani 1 1 d . . . C8 C 0.6142(4) 0.2976(3) 0.2908(4) 0.0397(11) Uani 1 1 d . . . C9 C 0.6984(4) 0.2061(3) 0.3893(4) 0.0394(11) Uani 1 1 d . . . C10 C 0.5924(4) 0.1133(3) 0.4327(4) 0.0420(12) Uani 1 1 d . . . C11 C 0.5461(5) 0.0672(3) 0.3521(4) 0.0443(13) Uani 1 1 d . . . H11A H 0.5822 0.0565 0.3004 0.053 Uiso 1 1 calc R . . C12 C 0.4458(5) 0.0368(3) 0.3484(4) 0.0427(12) Uani 1 1 d . . . C13 C 0.3918(4) 0.0512(3) 0.4230(4) 0.0425(12) Uani 1 1 d . . . H13A H 0.3218 0.0299 0.4187 0.051 Uiso 1 1 calc R . . C14 C 0.4428(4) 0.0976(3) 0.5041(4) 0.0454(13) Uani 1 1 d . . . H14A H 0.4078 0.1078 0.5567 0.054 Uiso 1 1 calc R . . C15 C 0.5443(5) 0.1291(3) 0.5095(4) 0.0475(13) Uani 1 1 d . . . H15A H 0.5794 0.1608 0.5651 0.057 Uiso 1 1 calc R . . C16 C 0.3345(5) 0.0126(3) 0.1792(4) 0.0418(12) Uani 1 1 d . . . C17 C 0.2345(5) -0.0063(3) 0.0173(4) 0.0448(13) Uani 1 1 d . . . C18 C 0.2494(4) 0.1045(3) 0.0813(4) 0.0403(11) Uani 1 1 d . . . C19 C 0.4172(4) 0.3014(3) 0.2309(4) 0.0393(11) Uani 1 1 d . . . C20 C 0.3743(4) 0.2508(3) 0.1565(4) 0.0406(11) Uani 1 1 d . . . H20A H 0.4154 0.2339 0.1117 0.049 Uiso 1 1 calc R . . C21 C 0.2695(4) 0.2247(3) 0.1477(4) 0.0390(11) Uani 1 1 d . . . C22 C 0.2078(5) 0.2483(3) 0.2115(4) 0.0451(12) Uani 1 1 d . . . H22A H 0.1362 0.2289 0.2051 0.054 Uiso 1 1 calc R . . C23 C 0.2536(5) 0.3013(3) 0.2854(5) 0.0508(14) Uani 1 1 d . . . H23A H 0.2118 0.3196 0.3288 0.061 Uiso 1 1 calc R . . C24 C 0.3590(5) 0.3277(3) 0.2964(4) 0.0470(13) Uani 1 1 d . . . H24A H 0.3907 0.3631 0.3479 0.056 Uiso 1 1 calc R . . C25 C 0.1390(5) -0.0288(3) -0.1569(4) 0.0470(13) Uani 1 1 d . . . C26 C 0.0260(6) -0.0271(4) -0.1862(6) 0.0653(19) Uani 1 1 d . . . C27 C -0.0329(6) -0.0020(5) -0.2818(9) 0.089(3) Uani 1 1 d . . . C28 C 0.0207(9) 0.0215(4) -0.3499(6) 0.085(3) Uani 1 1 d . . . C29 C 0.1356(7) 0.0206(3) -0.3229(5) 0.0639(18) Uani 1 1 d . . . C30 C 0.1930(5) -0.0043(3) -0.2260(4) 0.0461(13) 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 F1 0.057(2) 0.071(2) 0.055(2) -0.0155(18) 0.0159(16) -0.0029(17) F2 0.065(2) 0.066(2) 0.078(3) -0.008(2) 0.028(2) 0.0103(19) F3 0.049(2) 0.082(3) 0.066(2) 0.014(2) 0.0135(17) 0.0081(18) F4 0.068(2) 0.064(2) 0.055(2) -0.0033(18) 0.0109(17) -0.0171(18) F5 0.066(2) 0.0497(19) 0.075(2) -0.0127(18) 0.0262(19) -0.0027(17) F6 0.088(3) 0.114(4) 0.157(5) -0.052(4) 0.080(3) -0.050(3) F7 0.051(3) 0.145(5) 0.188(6) -0.098(5) -0.028(3) 0.012(3) F8 0.195(6) 0.106(4) 0.072(3) -0.040(3) -0.054(3) 0.081(4) F9 0.197(6) 0.076(3) 0.057(2) 0.002(2) 0.060(3) 0.003(3) F10 0.055(2) 0.063(2) 0.083(3) -0.005(2) 0.0321(19) -0.0039(17) O1 0.040(2) 0.049(2) 0.062(2) 0.0084(19) 0.0158(18) -0.0030(17) O2 0.038(2) 0.048(2) 0.063(2) 0.0221(19) 0.0053(17) -0.0014(17) O3 0.063(3) 0.0351(19) 0.045(2) 0.0027(17) 0.0054(18) -0.0009(17) O4 0.046(2) 0.0367(19) 0.054(2) 0.0081(17) 0.0082(17) -0.0002(16) O5 0.050(2) 0.0370(19) 0.0387(19) -0.0013(16) 0.0046(16) 0.0021(16) O6 0.083(3) 0.040(2) 0.044(2) -0.0062(18) 0.019(2) -0.010(2) N1 0.041(2) 0.041(2) 0.042(2) 0.003(2) 0.0110(19) -0.0038(19) N2 0.040(2) 0.040(2) 0.042(2) 0.0020(19) 0.0113(19) -0.0045(18) N3 0.040(2) 0.039(2) 0.045(2) 0.002(2) 0.0115(19) -0.0052(19) N4 0.040(2) 0.038(2) 0.041(2) -0.0015(19) 0.0111(19) -0.0033(18) N5 0.063(3) 0.036(2) 0.046(3) 0.003(2) 0.019(2) -0.002(2) N6 0.046(2) 0.037(2) 0.039(2) -0.0019(19) 0.0132(19) -0.0076(19) C1 0.046(3) 0.053(3) 0.051(3) -0.009(3) 0.020(3) -0.013(3) C2 0.045(3) 0.053(3) 0.067(4) 0.005(3) 0.030(3) 0.004(3) C3 0.040(3) 0.054(3) 0.056(3) 0.010(3) 0.017(3) 0.000(3) C4 0.050(3) 0.054(3) 0.045(3) -0.002(3) 0.012(3) -0.020(3) C5 0.054(3) 0.045(3) 0.056(3) 0.001(3) 0.028(3) -0.009(3) C6 0.044(3) 0.046(3) 0.046(3) 0.004(2) 0.020(2) -0.007(2) C7 0.030(2) 0.044(3) 0.044(3) -0.002(2) 0.013(2) -0.008(2) C8 0.049(3) 0.036(3) 0.032(2) -0.002(2) 0.007(2) 0.001(2) C9 0.036(3) 0.040(3) 0.042(3) 0.005(2) 0.010(2) 0.000(2) C10 0.035(3) 0.035(3) 0.052(3) 0.014(2) 0.005(2) -0.001(2) C11 0.049(3) 0.044(3) 0.046(3) 0.018(2) 0.022(2) 0.007(2) C12 0.051(3) 0.033(2) 0.038(3) 0.007(2) 0.002(2) 0.001(2) C13 0.034(3) 0.040(3) 0.052(3) 0.014(2) 0.008(2) 0.007(2) C14 0.040(3) 0.048(3) 0.050(3) 0.011(3) 0.015(2) 0.008(2) C15 0.048(3) 0.043(3) 0.047(3) 0.003(2) 0.007(3) 0.000(2) C16 0.049(3) 0.034(3) 0.042(3) 0.005(2) 0.013(2) 0.001(2) C17 0.057(3) 0.038(3) 0.046(3) -0.009(2) 0.027(3) -0.011(2) C18 0.042(3) 0.035(3) 0.045(3) -0.002(2) 0.015(2) -0.006(2) C19 0.040(3) 0.029(2) 0.048(3) 0.005(2) 0.011(2) -0.002(2) C20 0.043(3) 0.040(3) 0.041(3) 0.001(2) 0.014(2) 0.008(2) C21 0.042(3) 0.028(2) 0.043(3) -0.001(2) 0.005(2) 0.000(2) C22 0.051(3) 0.042(3) 0.046(3) 0.005(2) 0.020(3) 0.000(2) C23 0.060(4) 0.044(3) 0.056(3) -0.005(3) 0.029(3) 0.001(3) C24 0.058(3) 0.033(3) 0.051(3) -0.003(2) 0.017(3) -0.004(2) C25 0.047(3) 0.043(3) 0.047(3) -0.012(3) 0.006(2) -0.005(2) C26 0.056(4) 0.062(4) 0.082(5) -0.034(4) 0.025(4) -0.018(3) C27 0.051(4) 0.077(5) 0.115(7) -0.067(5) -0.012(4) 0.012(4) C28 0.105(7) 0.067(5) 0.057(4) -0.032(4) -0.019(5) 0.037(5) C29 0.100(6) 0.044(3) 0.044(3) -0.006(3) 0.014(4) 0.013(3) C30 0.044(3) 0.046(3) 0.052(3) -0.013(3) 0.020(3) -0.004(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 C1 1.336(6) . ? F2 C2 1.332(7) . ? F3 C3 1.337(6) . ? F4 C4 1.339(6) . ? F5 C5 1.352(7) . ? F6 C26 1.354(8) . ? F7 C27 1.348(9) . ? F8 C28 1.334(9) . ? F9 C29 1.324(9) . ? F10 C30 1.340(6) . ? O1 C7 1.376(6) . ? O1 C6 1.384(7) . ? O2 C9 1.326(6) . ? O2 C10 1.431(6) . ? O3 C16 1.330(6) . ? O3 C12 1.421(6) . ? O4 C8 1.341(6) . ? O4 C19 1.419(6) . ? O5 C18 1.352(6) . ? O5 C21 1.411(6) . ? O6 C17 1.358(6) . ? O6 C25 1.389(7) . ? N1 C7 1.318(7) . ? N1 C9 1.337(6) . ? N2 C8 1.330(6) . ? N2 C9 1.330(6) . ? N3 C7 1.304(7) . ? N3 C8 1.326(7) . ? N4 C18 1.315(7) . ? N4 C16 1.337(6) . ? N5 C16 1.322(7) . ? N5 C17 1.342(7) . ? N6 C17 1.319(7) . ? N6 C18 1.324(6) . ? C1 C2 1.383(8) . ? C1 C6 1.385(8) . ? C2 C3 1.372(9) . ? C3 C4 1.365(8) . ? C4 C5 1.391(8) . ? C5 C6 1.387(8) . ? C10 C11 1.365(8) . ? C10 C15 1.367(8) . ? C11 C12 1.367(8) . ? C11 H11A 0.9500 . ? C12 C13 1.386(8) . ? C13 C14 1.385(8) . ? C13 H13A 0.9500 . ? C14 C15 1.385(8) . ? C14 H14A 0.9500 . ? C15 H15A 0.9500 . ? C19 C20 1.356(7) . ? C19 C24 1.381(8) . ? C20 C21 1.376(7) . ? C20 H20A 0.9500 . ? C21 C22 1.378(8) . ? C22 C23 1.391(8) . ? C22 H22A 0.9500 . ? C23 C24 1.380(8) . ? C23 H23A 0.9500 . ? C24 H24A 0.9500 . ? C25 C26 1.363(9) . ? C25 C30 1.371(8) . ? C26 C27 1.366(12) . ? C27 C28 1.350(14) . ? C28 C29 1.388(12) . ? C29 C30 1.371(9) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 O1 C6 117.1(4) . . ? C9 O2 C10 115.8(4) . . ? C16 O3 C12 116.8(4) . . ? C8 O4 C19 119.0(4) . . ? C18 O5 C21 117.7(4) . . ? C17 O6 C25 116.7(4) . . ? C7 N1 C9 111.1(4) . . ? C8 N2 C9 112.4(4) . . ? C7 N3 C8 110.5(4) . . ? C18 N4 C16 113.3(4) . . ? C16 N5 C17 111.6(4) . . ? C17 N6 C18 112.1(5) . . ? F1 C1 C2 120.0(5) . . ? F1 C1 C6 119.1(5) . . ? C2 C1 C6 120.9(5) . . ? F2 C2 C3 120.3(5) . . ? F2 C2 C1 119.6(6) . . ? C3 C2 C1 120.1(6) . . ? F3 C3 C4 119.3(6) . . ? F3 C3 C2 120.5(5) . . ? C4 C3 C2 120.2(5) . . ? F4 C4 C3 120.4(6) . . ? F4 C4 C5 119.8(6) . . ? C3 C4 C5 119.7(5) . . ? F5 C5 C6 119.3(5) . . ? F5 C5 C4 119.7(5) . . ? C6 C5 C4 121.0(5) . . ? O1 C6 C1 122.1(5) . . ? O1 C6 C5 119.9(5) . . ? C1 C6 C5 118.0(5) . . ? N3 C7 N1 130.8(4) . . ? N3 C7 O1 112.6(4) . . ? N1 C7 O1 116.6(4) . . ? N3 C8 N2 128.3(5) . . ? N3 C8 O4 114.1(4) . . ? N2 C8 O4 117.6(5) . . ? O2 C9 N2 119.2(4) . . ? O2 C9 N1 114.0(4) . . ? N2 C9 N1 126.8(5) . . ? C11 C10 C15 123.1(5) . . ? C11 C10 O2 118.2(5) . . ? C15 C10 O2 118.6(5) . . ? C10 C11 C12 117.5(5) . . ? C10 C11 H11A 121.2 . . ? C12 C11 H11A 121.2 . . ? C11 C12 C13 122.3(5) . . ? C11 C12 O3 118.9(5) . . ? C13 C12 O3 118.7(5) . . ? C14 C13 C12 118.0(5) . . ? C14 C13 H13A 121.0 . . ? C12 C13 H13A 121.0 . . ? C15 C14 C13 120.8(5) . . ? C15 C14 H14A 119.6 . . ? C13 C14 H14A 119.6 . . ? C10 C15 C14 118.2(5) . . ? C10 C15 H15A 120.9 . . ? C14 C15 H15A 120.9 . . ? N5 C16 O3 114.4(4) . . ? N5 C16 N4 127.0(5) . . ? O3 C16 N4 118.6(5) . . ? N6 C17 N5 128.5(5) . . ? N6 C17 O6 119.1(5) . . ? N5 C17 O6 112.5(5) . . ? N4 C18 N6 127.5(5) . . ? N4 C18 O5 118.5(4) . . ? N6 C18 O5 114.0(4) . . ? C20 C19 C24 122.2(5) . . ? C20 C19 O4 119.4(5) . . ? C24 C19 O4 118.2(5) . . ? C19 C20 C21 118.2(5) . . ? C19 C20 H20A 120.9 . . ? C21 C20 H20A 120.9 . . ? C20 C21 C22 122.2(5) . . ? C20 C21 O5 118.7(5) . . ? C22 C21 O5 119.0(5) . . ? C21 C22 C23 118.0(5) . . ? C21 C22 H22A 121.0 . . ? C23 C22 H22A 121.0 . . ? C24 C23 C22 120.8(5) . . ? C24 C23 H23A 119.6 . . ? C22 C23 H23A 119.6 . . ? C23 C24 C19 118.6(5) . . ? C23 C24 H24A 120.7 . . ? C19 C24 H24A 120.7 . . ? C26 C25 C30 118.4(6) . . ? C26 C25 O6 120.9(6) . . ? C30 C25 O6 120.7(5) . . ? F6 C26 C25 119.2(7) . . ? F6 C26 C27 119.4(7) . . ? C25 C26 C27 121.3(7) . . ? F7 C27 C28 120.3(10) . . ? F7 C27 C26 119.7(10) . . ? C28 C27 C26 120.0(7) . . ? F8 C28 C27 120.6(10) . . ? F8 C28 C29 118.9(10) . . ? C27 C28 C29 120.3(7) . . ? F9 C29 C30 120.5(7) . . ? F9 C29 C28 120.9(7) . . ? C30 C29 C28 118.6(7) . . ? F10 C30 C25 118.4(5) . . ? F10 C30 C29 120.2(6) . . ? C25 C30 C29 121.4(6) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag F1 C1 C2 F2 0.5(8) . . . . ? C6 C1 C2 F2 -179.9(5) . . . . ? F1 C1 C2 C3 179.1(5) . . . . ? C6 C1 C2 C3 -1.3(9) . . . . ? F2 C2 C3 F3 -0.2(8) . . . . ? C1 C2 C3 F3 -178.9(5) . . . . ? F2 C2 C3 C4 -179.5(5) . . . . ? C1 C2 C3 C4 1.8(8) . . . . ? F3 C3 C4 F4 -2.5(8) . . . . ? C2 C3 C4 F4 176.8(5) . . . . ? F3 C3 C4 C5 179.3(5) . . . . ? C2 C3 C4 C5 -1.4(8) . . . . ? F4 C4 C5 F5 1.2(8) . . . . ? C3 C4 C5 F5 179.4(5) . . . . ? F4 C4 C5 C6 -177.8(5) . . . . ? C3 C4 C5 C6 0.4(8) . . . . ? C7 O1 C6 C1 74.0(6) . . . . ? C7 O1 C6 C5 -108.7(6) . . . . ? F1 C1 C6 O1 -2.7(8) . . . . ? C2 C1 C6 O1 177.7(5) . . . . ? F1 C1 C6 C5 179.9(5) . . . . ? C2 C1 C6 C5 0.3(8) . . . . ? F5 C5 C6 O1 3.7(7) . . . . ? C4 C5 C6 O1 -177.3(5) . . . . ? F5 C5 C6 C1 -178.9(5) . . . . ? C4 C5 C6 C1 0.1(8) . . . . ? C8 N3 C7 N1 1.4(8) . . . . ? C8 N3 C7 O1 -178.1(4) . . . . ? C9 N1 C7 N3 -0.2(8) . . . . ? C9 N1 C7 O1 179.3(4) . . . . ? C6 O1 C7 N3 175.8(5) . . . . ? C6 O1 C7 N1 -3.8(7) . . . . ? C7 N3 C8 N2 -1.5(8) . . . . ? C7 N3 C8 O4 178.3(4) . . . . ? C9 N2 C8 N3 0.5(8) . . . . ? C9 N2 C8 O4 -179.4(4) . . . . ? C19 O4 C8 N3 178.0(4) . . . . ? C19 O4 C8 N2 -2.2(7) . . . . ? C10 O2 C9 N2 0.4(7) . . . . ? C10 O2 C9 N1 -180.0(5) . . . . ? C8 N2 C9 O2 -179.4(5) . . . . ? C8 N2 C9 N1 1.1(8) . . . . ? C7 N1 C9 O2 179.2(5) . . . . ? C7 N1 C9 N2 -1.2(8) . . . . ? C9 O2 C10 C11 89.2(6) . . . . ? C9 O2 C10 C15 -93.7(6) . . . . ? C15 C10 C11 C12 1.2(8) . . . . ? O2 C10 C11 C12 178.1(4) . . . . ? C10 C11 C12 C13 -0.3(8) . . . . ? C10 C11 C12 O3 -176.9(4) . . . . ? C16 O3 C12 C11 -88.3(6) . . . . ? C16 O3 C12 C13 95.0(6) . . . . ? C11 C12 C13 C14 -0.6(8) . . . . ? O3 C12 C13 C14 176.0(4) . . . . ? C12 C13 C14 C15 0.7(7) . . . . ? C11 C10 C15 C14 -1.0(8) . . . . ? O2 C10 C15 C14 -178.0(4) . . . . ? C13 C14 C15 C10 0.1(8) . . . . ? C17 N5 C16 O3 179.7(5) . . . . ? C17 N5 C16 N4 -0.8(8) . . . . ? C12 O3 C16 N5 175.5(5) . . . . ? C12 O3 C16 N4 -4.0(7) . . . . ? C18 N4 C16 N5 1.4(8) . . . . ? C18 N4 C16 O3 -179.2(5) . . . . ? C18 N6 C17 N5 -0.6(8) . . . . ? C18 N6 C17 O6 -179.1(5) . . . . ? C16 N5 C17 N6 0.4(8) . . . . ? C16 N5 C17 O6 179.0(4) . . . . ? C25 O6 C17 N6 3.9(7) . . . . ? C25 O6 C17 N5 -174.8(5) . . . . ? C16 N4 C18 N6 -1.7(8) . . . . ? C16 N4 C18 O5 178.5(5) . . . . ? C17 N6 C18 N4 1.3(7) . . . . ? C17 N6 C18 O5 -178.8(4) . . . . ? C21 O5 C18 N4 4.3(7) . . . . ? C21 O5 C18 N6 -175.6(4) . . . . ? C8 O4 C19 C20 -84.5(6) . . . . ? C8 O4 C19 C24 100.1(6) . . . . ? C24 C19 C20 C21 -0.8(8) . . . . ? O4 C19 C20 C21 -175.9(4) . . . . ? C19 C20 C21 C22 0.1(8) . . . . ? C19 C20 C21 O5 176.0(4) . . . . ? C18 O5 C21 C20 82.3(6) . . . . ? C18 O5 C21 C22 -101.7(5) . . . . ? C20 C21 C22 C23 1.2(8) . . . . ? O5 C21 C22 C23 -174.7(5) . . . . ? C21 C22 C23 C24 -2.0(8) . . . . ? C22 C23 C24 C19 1.3(9) . . . . ? C20 C19 C24 C23 0.1(8) . . . . ? O4 C19 C24 C23 175.3(5) . . . . ? C17 O6 C25 C26 -95.2(6) . . . . ? C17 O6 C25 C30 85.9(6) . . . . ? C30 C25 C26 F6 -178.4(5) . . . . ? O6 C25 C26 F6 2.7(9) . . . . ? C30 C25 C26 C27 0.2(9) . . . . ? O6 C25 C26 C27 -178.7(5) . . . . ? F6 C26 C27 F7 1.3(10) . . . . ? C25 C26 C27 F7 -177.3(6) . . . . ? F6 C26 C27 C28 179.0(6) . . . . ? C25 C26 C27 C28 0.4(10) . . . . ? F7 C27 C28 F8 2.3(11) . . . . ? C26 C27 C28 F8 -175.5(6) . . . . ? F7 C27 C28 C29 177.3(6) . . . . ? C26 C27 C28 C29 -0.4(11) . . . . ? F8 C28 C29 F9 -2.7(9) . . . . ? C27 C28 C29 F9 -177.9(6) . . . . ? F8 C28 C29 C30 174.9(5) . . . . ? C27 C28 C29 C30 -0.2(10) . . . . ? C26 C25 C30 F10 177.1(5) . . . . ? O6 C25 C30 F10 -4.1(8) . . . . ? C26 C25 C30 C29 -0.8(8) . . . . ? O6 C25 C30 C29 178.1(5) . . . . ? F9 C29 C30 F10 0.6(8) . . . . ? C28 C29 C30 F10 -177.0(5) . . . . ? F9 C29 C30 C25 178.5(5) . . . . ? C28 C29 C30 C25 0.8(9) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.388 _refine_diff_density_min -0.432 _refine_diff_density_rms 0.111 data_sa185 _database_code_depnum_ccdc_archive 'CCDC 897875' #TrackingRef '5a-cl complex.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H18 N6 O6, C8 H20 N, H2 O, Cl' _chemical_formula_sum 'C38 H40 Cl N7 O7' _chemical_formula_weight 742.22 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 12.102(2) _cell_length_b 12.290(3) _cell_length_c 13.841(3) _cell_angle_alpha 66.29(3) _cell_angle_beta 76.08(3) _cell_angle_gamma 86.19(3) _cell_volume 1828.6(6) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 378 _cell_measurement_theta_min 2.17 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.348 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 780 _exptl_absorpt_coefficient_mu 0.165 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9508 _exptl_absorpt_correction_T_max 0.9663 _exptl_absorpt_process_details 'CrystalClear (Rigaku Inc., 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Saturn724+ CCD' _diffrn_measurement_method '\w scans at fixed \c = 45\%' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22538 _diffrn_reflns_av_R_equivalents 0.0309 _diffrn_reflns_av_sigmaI/netI 0.0322 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.90 _diffrn_reflns_theta_max 27.48 _reflns_number_total 8339 _reflns_number_gt 7266 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP in Siemens SHELXTL (Sheldrick, 1994)' _computing_publication_material 'SHELX97 (Sheldrick, 1997)' _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^)+(0.0435P)^2^+0.5631P] 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 8339 _refine_ls_number_parameters 480 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0610 _refine_ls_R_factor_gt 0.0508 _refine_ls_wR_factor_ref 0.1183 _refine_ls_wR_factor_gt 0.1127 _refine_ls_goodness_of_fit_ref 1.110 _refine_ls_restrained_S_all 1.110 _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 Cl1 Cl 0.82945(4) 0.14588(4) 0.01264(4) 0.04541(13) Uani 1 1 d . . . O1 O 0.67759(11) -0.23654(11) 0.36728(12) 0.0471(3) Uani 1 1 d . . . O2 O 0.48130(10) 0.11472(11) 0.19932(10) 0.0424(3) Uani 1 1 d . . . O3 O 0.77669(10) 0.34642(9) 0.17849(9) 0.0320(3) Uani 1 1 d . . . O4 O 0.95419(9) -0.00904(10) 0.38047(9) 0.0325(3) Uani 1 1 d . . . O5 O 1.03465(10) -0.35704(11) 0.34427(11) 0.0428(3) Uani 1 1 d . . . O6 O 0.61273(10) 0.43237(11) -0.10391(9) 0.0373(3) Uani 1 1 d . . . N1 N 0.85713(13) -0.29530(13) 0.35133(13) 0.0401(3) Uani 1 1 d . . . N2 N 0.80850(11) -0.11472(12) 0.37429(11) 0.0310(3) Uani 1 1 d . . . N3 N 0.99849(11) -0.18161(11) 0.36745(10) 0.0299(3) Uani 1 1 d . . . N4 N 0.54668(12) 0.27378(12) 0.04774(11) 0.0345(3) Uani 1 1 d . . . N5 N 0.69633(11) 0.39569(11) 0.03892(10) 0.0290(3) Uani 1 1 d . . . N6 N 0.62971(11) 0.22248(12) 0.19945(11) 0.0298(3) Uani 1 1 d . . . N7 N 0.22923(11) 0.23558(12) -0.00442(11) 0.0308(3) Uani 1 1 d . . . C1 C 0.96230(15) -0.27257(14) 0.35419(14) 0.0342(4) Uani 1 1 d . . . C2 C 0.78601(14) -0.21326(15) 0.36401(14) 0.0352(4) Uani 1 1 d . . . C3 C 0.91719(13) -0.10484(13) 0.37236(12) 0.0280(3) Uani 1 1 d . . . C4 C 0.59568(14) -0.15228(15) 0.37577(15) 0.0360(4) Uani 1 1 d . . . C5 C 0.51939(16) -0.17688(16) 0.47398(15) 0.0421(4) Uani 1 1 d . . . H5A H 0.5264 -0.2458 0.5361 0.051 Uiso 1 1 calc R . . C6 C 0.43283(16) -0.09979(18) 0.48054(15) 0.0447(4) Uani 1 1 d . . . H6A H 0.3808 -0.1142 0.5482 0.054 Uiso 1 1 calc R . . C7 C 0.42098(14) -0.00131(16) 0.38919(15) 0.0396(4) Uani 1 1 d . . . H7A H 0.3596 0.0504 0.3929 0.047 Uiso 1 1 calc R . . C8 C 0.49960(14) 0.02026(15) 0.29305(14) 0.0340(4) Uani 1 1 d . . . C9 C 0.58876(14) -0.05337(15) 0.28381(14) 0.0351(4) Uani 1 1 d . . . H9A H 0.6431 -0.0367 0.2170 0.042 Uiso 1 1 calc R . . C10 C 0.55709(13) 0.20665(15) 0.14748(13) 0.0328(3) Uani 1 1 d . . . C11 C 0.62104(13) 0.36555(14) -0.00209(13) 0.0306(3) Uani 1 1 d . . . C12 C 0.69759(13) 0.31781(13) 0.13832(13) 0.0279(3) Uani 1 1 d . . . C13 C 0.80217(13) 0.26461(13) 0.27555(12) 0.0277(3) Uani 1 1 d . . . C14 C 0.78601(14) 0.30130(15) 0.35989(13) 0.0332(4) Uani 1 1 d . . . H14A H 0.7527 0.3753 0.3538 0.040 Uiso 1 1 calc R . . C15 C 0.81934(15) 0.22810(15) 0.45345(14) 0.0358(4) Uani 1 1 d . . . H15A H 0.8075 0.2512 0.5128 0.043 Uiso 1 1 calc R . . C16 C 0.86962(13) 0.12185(14) 0.46103(13) 0.0308(3) Uani 1 1 d . . . H16A H 0.8928 0.0717 0.5251 0.037 Uiso 1 1 calc R . . C17 C 0.88567(12) 0.08957(13) 0.37417(13) 0.0279(3) Uani 1 1 d . . . C18 C 0.85228(13) 0.15913(14) 0.27987(13) 0.0290(3) Uani 1 1 d . . . H18A H 0.8633 0.1355 0.2209 0.035 Uiso 1 1 calc R . . C19 C 1.14901(14) -0.34839(15) 0.34803(15) 0.0366(4) Uani 1 1 d . . . C20 C 1.22233(17) -0.26076(18) 0.26713(16) 0.0468(5) Uani 1 1 d . . . H20A H 1.1966 -0.2008 0.2089 0.056 Uiso 1 1 calc R . . C21 C 1.33521(18) -0.2626(2) 0.2732(2) 0.0591(6) Uani 1 1 d . . . H21A H 1.3876 -0.2020 0.2190 0.071 Uiso 1 1 calc R . . C22 C 1.37239(18) -0.3513(2) 0.3569(2) 0.0589(6) Uani 1 1 d . . . H22A H 1.4498 -0.3512 0.3604 0.071 Uiso 1 1 calc R . . C23 C 1.29782(18) -0.43940(18) 0.43477(19) 0.0518(5) Uani 1 1 d . . . H23A H 1.3241 -0.5016 0.4913 0.062 Uiso 1 1 calc R . . C24 C 1.18425(16) -0.43830(16) 0.43156(16) 0.0425(4) Uani 1 1 d . . . H24A H 1.1318 -0.4985 0.4860 0.051 Uiso 1 1 calc R . . C25 C 0.70021(14) 0.51435(14) -0.17818(13) 0.0326(3) Uani 1 1 d . . . C26 C 0.66429(17) 0.61682(16) -0.25071(14) 0.0420(4) Uani 1 1 d . . . H26A H 0.5854 0.6316 -0.2450 0.050 Uiso 1 1 calc R . . C27 C 0.7456(2) 0.69775(17) -0.33209(16) 0.0502(5) Uani 1 1 d . . . H27A H 0.7223 0.7681 -0.3834 0.060 Uiso 1 1 calc R . . C28 C 0.85982(19) 0.67683(18) -0.33901(16) 0.0499(5) Uani 1 1 d . . . H28A H 0.9152 0.7335 -0.3938 0.060 Uiso 1 1 calc R . . C29 C 0.89349(17) 0.57298(18) -0.26583(15) 0.0456(4) Uani 1 1 d . . . H29A H 0.9723 0.5586 -0.2707 0.055 Uiso 1 1 calc R . . C30 C 0.81365(15) 0.48955(16) -0.18551(14) 0.0370(4) Uani 1 1 d . . . H30A H 0.8367 0.4170 -0.1367 0.044 Uiso 1 1 calc R . . C31 C 0.26159(15) 0.12590(15) -0.02807(16) 0.0393(4) Uani 1 1 d . . . H31A H 0.2059 0.0606 0.0223 0.047 Uiso 1 1 calc R . . H31B H 0.2551 0.1431 -0.1027 0.047 Uiso 1 1 calc R . . C32 C 0.37971(17) 0.08346(18) -0.01791(18) 0.0482(5) Uani 1 1 d . . . H32A H 0.3933 0.0128 -0.0348 0.072 Uiso 1 1 calc R . . H32B H 0.3866 0.0635 0.0564 0.072 Uiso 1 1 calc R . . H32C H 0.4360 0.1465 -0.0688 0.072 Uiso 1 1 calc R . . C33 C 0.10727(14) 0.25891(16) -0.01645(17) 0.0399(4) Uani 1 1 d . . . H33A H 0.1046 0.2676 -0.0901 0.048 Uiso 1 1 calc R . . H33B H 0.0588 0.1884 0.0362 0.048 Uiso 1 1 calc R . . C34 C 0.05642(16) 0.36752(18) 0.00059(19) 0.0497(5) Uani 1 1 d . . . H34A H -0.0214 0.3759 -0.0099 0.075 Uiso 1 1 calc R . . H34B H 0.1027 0.4384 -0.0518 0.075 Uiso 1 1 calc R . . H34C H 0.0550 0.3586 0.0745 0.075 Uiso 1 1 calc R . . C35 C 0.30835(15) 0.34108(15) -0.08009(14) 0.0374(4) Uani 1 1 d . . . H35A H 0.2838 0.4094 -0.0604 0.045 Uiso 1 1 calc R . . H35B H 0.3859 0.3219 -0.0680 0.045 Uiso 1 1 calc R . . C36 C 0.3144(2) 0.3787(2) -0.19919(17) 0.0584(6) Uani 1 1 d . . . H36A H 0.3675 0.4473 -0.2414 0.088 Uiso 1 1 calc R . . H36B H 0.2386 0.4005 -0.2130 0.088 Uiso 1 1 calc R . . H36C H 0.3411 0.3128 -0.2206 0.088 Uiso 1 1 calc R . . C37 C 0.23835(15) 0.21462(16) 0.10911(14) 0.0371(4) Uani 1 1 d . . . H37A H 0.3199 0.2100 0.1107 0.045 Uiso 1 1 calc R . . H37B H 0.2083 0.2843 0.1246 0.045 Uiso 1 1 calc R . . C38 C 0.1766(2) 0.1046(2) 0.19805(18) 0.0620(6) Uani 1 1 d . . . H38A H 0.1873 0.0984 0.2680 0.093 Uiso 1 1 calc R . . H38B H 0.2072 0.0345 0.1851 0.093 Uiso 1 1 calc R . . H38C H 0.0953 0.1090 0.1991 0.093 Uiso 1 1 calc R . . O1W O 0.96918(14) -0.06127(15) 0.14167(11) 0.0674(5) Uani 1 1 d . . . H1W H 0.9266 -0.0128 0.1063 0.078(9) Uiso 1 1 d R . . H2W H 1.0186 -0.0870 0.1027 0.079(9) Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0451(3) 0.0415(2) 0.0567(3) -0.0261(2) -0.0152(2) 0.00935(19) O1 0.0356(7) 0.0352(6) 0.0791(10) -0.0264(7) -0.0227(6) 0.0022(5) O2 0.0332(6) 0.0413(7) 0.0431(7) 0.0001(6) -0.0186(5) -0.0091(5) O3 0.0378(6) 0.0295(6) 0.0301(6) -0.0083(5) -0.0159(5) -0.0024(5) O4 0.0314(6) 0.0308(6) 0.0427(7) -0.0186(5) -0.0162(5) 0.0055(5) O5 0.0396(7) 0.0366(6) 0.0634(9) -0.0283(6) -0.0196(6) 0.0091(5) O6 0.0374(6) 0.0417(6) 0.0296(6) -0.0061(5) -0.0150(5) -0.0032(5) N1 0.0383(8) 0.0328(7) 0.0554(10) -0.0201(7) -0.0181(7) 0.0035(6) N2 0.0301(7) 0.0306(7) 0.0321(7) -0.0112(6) -0.0090(5) 0.0001(5) N3 0.0328(7) 0.0292(7) 0.0287(7) -0.0113(6) -0.0099(5) 0.0040(5) N4 0.0305(7) 0.0383(7) 0.0334(8) -0.0094(6) -0.0131(6) -0.0016(6) N5 0.0318(7) 0.0285(6) 0.0281(7) -0.0107(6) -0.0107(5) 0.0020(5) N6 0.0267(6) 0.0319(7) 0.0293(7) -0.0092(6) -0.0090(5) 0.0000(5) N7 0.0262(6) 0.0310(7) 0.0420(8) -0.0198(6) -0.0114(6) 0.0029(5) C1 0.0380(9) 0.0296(8) 0.0368(9) -0.0137(7) -0.0124(7) 0.0053(7) C2 0.0350(9) 0.0304(8) 0.0409(10) -0.0119(7) -0.0139(7) 0.0003(7) C3 0.0326(8) 0.0276(7) 0.0225(7) -0.0074(6) -0.0085(6) 0.0001(6) C4 0.0302(8) 0.0325(8) 0.0491(10) -0.0166(8) -0.0147(7) -0.0019(7) C5 0.0395(10) 0.0398(9) 0.0399(10) -0.0035(8) -0.0154(8) -0.0092(8) C6 0.0358(9) 0.0537(11) 0.0372(10) -0.0131(9) -0.0014(8) -0.0091(8) C7 0.0272(8) 0.0424(10) 0.0450(10) -0.0139(8) -0.0068(7) -0.0011(7) C8 0.0301(8) 0.0346(8) 0.0337(9) -0.0056(7) -0.0130(7) -0.0066(7) C9 0.0297(8) 0.0425(9) 0.0351(9) -0.0169(8) -0.0070(7) -0.0046(7) C10 0.0263(8) 0.0351(8) 0.0342(9) -0.0096(7) -0.0091(6) -0.0001(6) C11 0.0314(8) 0.0327(8) 0.0283(8) -0.0109(7) -0.0109(6) 0.0040(6) C12 0.0279(7) 0.0289(7) 0.0302(8) -0.0138(7) -0.0096(6) 0.0036(6) C13 0.0285(7) 0.0287(7) 0.0255(8) -0.0079(6) -0.0101(6) -0.0018(6) C14 0.0355(8) 0.0338(8) 0.0368(9) -0.0187(7) -0.0134(7) 0.0067(7) C15 0.0392(9) 0.0434(9) 0.0336(9) -0.0225(8) -0.0130(7) 0.0066(7) C16 0.0298(8) 0.0364(8) 0.0288(8) -0.0130(7) -0.0120(6) 0.0032(6) C17 0.0237(7) 0.0281(7) 0.0353(8) -0.0146(7) -0.0098(6) 0.0018(6) C18 0.0295(8) 0.0324(8) 0.0285(8) -0.0146(7) -0.0082(6) -0.0004(6) C19 0.0353(9) 0.0358(9) 0.0467(10) -0.0247(8) -0.0103(7) 0.0057(7) C20 0.0515(11) 0.0477(11) 0.0397(10) -0.0193(9) -0.0050(8) 0.0025(9) C21 0.0438(11) 0.0653(14) 0.0656(15) -0.0336(12) 0.0071(10) -0.0058(10) C22 0.0367(11) 0.0707(15) 0.0901(17) -0.0544(14) -0.0153(11) 0.0114(10) C23 0.0523(12) 0.0454(11) 0.0727(15) -0.0335(11) -0.0284(11) 0.0177(9) C24 0.0460(10) 0.0332(9) 0.0524(11) -0.0208(8) -0.0135(9) 0.0063(8) C25 0.0403(9) 0.0326(8) 0.0265(8) -0.0120(7) -0.0099(7) -0.0014(7) C26 0.0522(11) 0.0395(9) 0.0347(9) -0.0135(8) -0.0150(8) 0.0084(8) C27 0.0776(15) 0.0332(9) 0.0347(10) -0.0087(8) -0.0124(10) 0.0025(9) C28 0.0672(14) 0.0432(10) 0.0352(10) -0.0146(9) -0.0021(9) -0.0146(10) C29 0.0451(10) 0.0555(12) 0.0399(10) -0.0242(9) -0.0054(8) -0.0060(9) C30 0.0436(10) 0.0383(9) 0.0307(9) -0.0144(7) -0.0105(7) 0.0010(7) C31 0.0405(9) 0.0364(9) 0.0547(11) -0.0283(9) -0.0205(8) 0.0114(7) C32 0.0438(10) 0.0504(11) 0.0640(13) -0.0341(10) -0.0219(9) 0.0194(9) C33 0.0274(8) 0.0406(9) 0.0615(12) -0.0266(9) -0.0184(8) 0.0058(7) C34 0.0343(9) 0.0472(11) 0.0752(14) -0.0316(11) -0.0167(9) 0.0136(8) C35 0.0333(9) 0.0348(9) 0.0445(10) -0.0159(8) -0.0088(7) -0.0011(7) C36 0.0658(14) 0.0575(13) 0.0443(12) -0.0141(10) -0.0106(10) 0.0023(11) C37 0.0354(9) 0.0419(9) 0.0393(10) -0.0209(8) -0.0103(7) 0.0032(7) C38 0.0609(14) 0.0667(14) 0.0450(12) -0.0119(11) -0.0024(10) -0.0135(11) O1W 0.0746(11) 0.0875(12) 0.0322(7) -0.0182(8) -0.0152(7) 0.0293(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 O1 C2 1.348(2) . ? O1 C4 1.405(2) . ? O2 C10 1.342(2) . ? O2 C8 1.405(2) . ? O3 C12 1.3443(18) . ? O3 C13 1.4081(18) . ? O4 C3 1.3416(19) . ? O4 C17 1.4072(18) . ? O5 C1 1.341(2) . ? O5 C19 1.410(2) . ? O6 C11 1.3406(19) . ? O6 C25 1.407(2) . ? N1 C2 1.320(2) . ? N1 C1 1.334(2) . ? N2 C3 1.322(2) . ? N2 C2 1.328(2) . ? N3 C1 1.321(2) . ? N3 C3 1.326(2) . ? N4 C10 1.325(2) . ? N4 C11 1.330(2) . ? N5 C11 1.324(2) . ? N5 C12 1.326(2) . ? N6 C12 1.327(2) . ? N6 C10 1.329(2) . ? N7 C35 1.512(2) . ? N7 C31 1.517(2) . ? N7 C37 1.517(2) . ? N7 C33 1.521(2) . ? C4 C5 1.376(3) . ? C4 C9 1.378(2) . ? C5 C6 1.377(3) . ? C5 H5A 0.9500 . ? C6 C7 1.385(3) . ? C6 H6A 0.9500 . ? C7 C8 1.374(3) . ? C7 H7A 0.9500 . ? C8 C9 1.377(2) . ? C9 H9A 0.9500 . ? C13 C18 1.379(2) . ? C13 C14 1.380(2) . ? C14 C15 1.384(2) . ? C14 H14A 0.9500 . ? C15 C16 1.379(2) . ? C15 H15A 0.9500 . ? C16 C17 1.379(2) . ? C16 H16A 0.9500 . ? C17 C18 1.381(2) . ? C18 H18A 0.9500 . ? C19 C20 1.371(3) . ? C19 C24 1.374(3) . ? C20 C21 1.387(3) . ? C20 H20A 0.9500 . ? C21 C22 1.380(3) . ? C21 H21A 0.9500 . ? C22 C23 1.368(3) . ? C22 H22A 0.9500 . ? C23 C24 1.385(3) . ? C23 H23A 0.9500 . ? C24 H24A 0.9500 . ? C25 C30 1.375(2) . ? C25 C26 1.380(2) . ? C26 C27 1.386(3) . ? C26 H26A 0.9500 . ? C27 C28 1.377(3) . ? C27 H27A 0.9500 . ? C28 C29 1.382(3) . ? C28 H28A 0.9500 . ? C29 C30 1.385(3) . ? C29 H29A 0.9500 . ? C30 H30A 0.9500 . ? C31 C32 1.508(2) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C33 C34 1.513(2) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? C35 C36 1.507(3) . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? C37 C38 1.502(3) . ? C37 H37A 0.9900 . ? C37 H37B 0.9900 . ? C38 H38A 0.9800 . ? C38 H38B 0.9800 . ? C38 H38C 0.9800 . ? O1W H1W 0.8400 . ? O1W H2W 0.8400 . ? 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 O1 C4 118.23(13) . . ? C10 O2 C8 119.25(13) . . ? C12 O3 C13 120.03(12) . . ? C3 O4 C17 121.93(12) . . ? C1 O5 C19 119.90(13) . . ? C11 O6 C25 121.18(13) . . ? C2 N1 C1 111.87(14) . . ? C3 N2 C2 111.62(14) . . ? C1 N3 C3 111.94(14) . . ? C10 N4 C11 112.57(14) . . ? C11 N5 C12 112.53(13) . . ? C12 N6 C10 111.85(14) . . ? C35 N7 C31 112.01(13) . . ? C35 N7 C37 105.66(13) . . ? C31 N7 C37 110.84(13) . . ? C35 N7 C33 111.71(13) . . ? C31 N7 C33 105.53(12) . . ? C37 N7 C33 111.22(13) . . ? N3 C1 N1 127.75(15) . . ? N3 C1 O5 119.85(15) . . ? N1 C1 O5 112.39(14) . . ? N1 C2 N2 128.30(16) . . ? N1 C2 O1 113.54(15) . . ? N2 C2 O1 118.16(15) . . ? N2 C3 N3 128.28(15) . . ? N2 C3 O4 119.05(14) . . ? N3 C3 O4 112.62(13) . . ? C5 C4 C9 122.50(17) . . ? C5 C4 O1 118.39(16) . . ? C9 C4 O1 118.88(16) . . ? C4 C5 C6 118.74(17) . . ? C4 C5 H5A 120.6 . . ? C6 C5 H5A 120.6 . . ? C5 C6 C7 120.48(17) . . ? C5 C6 H6A 119.8 . . ? C7 C6 H6A 119.8 . . ? C8 C7 C6 118.76(17) . . ? C8 C7 H7A 120.6 . . ? C6 C7 H7A 120.6 . . ? C7 C8 C9 122.44(16) . . ? C7 C8 O2 118.06(16) . . ? C9 C8 O2 119.22(16) . . ? C8 C9 C4 117.04(16) . . ? C8 C9 H9A 121.5 . . ? C4 C9 H9A 121.5 . . ? N4 C10 N6 127.79(15) . . ? N4 C10 O2 113.17(14) . . ? N6 C10 O2 119.01(14) . . ? N5 C11 N4 127.15(15) . . ? N5 C11 O6 119.92(14) . . ? N4 C11 O6 112.91(14) . . ? N5 C12 N6 127.94(14) . . ? N5 C12 O3 112.48(13) . . ? N6 C12 O3 119.53(14) . . ? C18 C13 C14 122.69(15) . . ? C18 C13 O3 120.29(14) . . ? C14 C13 O3 116.65(14) . . ? C13 C14 C15 118.65(15) . . ? C13 C14 H14A 120.7 . . ? C15 C14 H14A 120.7 . . ? C16 C15 C14 120.42(15) . . ? C16 C15 H15A 119.8 . . ? C14 C15 H15A 119.8 . . ? C17 C16 C15 118.96(15) . . ? C17 C16 H16A 120.5 . . ? C15 C16 H16A 120.5 . . ? C16 C17 C18 122.52(14) . . ? C16 C17 O4 115.51(14) . . ? C18 C17 O4 121.24(14) . . ? C13 C18 C17 116.74(14) . . ? C13 C18 H18A 121.6 . . ? C17 C18 H18A 121.6 . . ? C20 C19 C24 122.46(18) . . ? C20 C19 O5 121.24(17) . . ? C24 C19 O5 116.06(16) . . ? C19 C20 C21 117.8(2) . . ? C19 C20 H20A 121.1 . . ? C21 C20 H20A 121.1 . . ? C22 C21 C20 120.8(2) . . ? C22 C21 H21A 119.6 . . ? C20 C21 H21A 119.6 . . ? C23 C22 C21 120.0(2) . . ? C23 C22 H22A 120.0 . . ? C21 C22 H22A 120.0 . . ? C22 C23 C24 120.2(2) . . ? C22 C23 H23A 119.9 . . ? C24 C23 H23A 119.9 . . ? C19 C24 C23 118.64(19) . . ? C19 C24 H24A 120.7 . . ? C23 C24 H24A 120.7 . . ? C30 C25 C26 121.97(17) . . ? C30 C25 O6 122.57(15) . . ? C26 C25 O6 115.15(16) . . ? C25 C26 C27 118.68(19) . . ? C25 C26 H26A 120.7 . . ? C27 C26 H26A 120.7 . . ? C28 C27 C26 120.47(18) . . ? C28 C27 H27A 119.8 . . ? C26 C27 H27A 119.8 . . ? C27 C28 C29 119.67(19) . . ? C27 C28 H28A 120.2 . . ? C29 C28 H28A 120.2 . . ? C28 C29 C30 120.80(19) . . ? C28 C29 H29A 119.6 . . ? C30 C29 H29A 119.6 . . ? C25 C30 C29 118.36(17) . . ? C25 C30 H30A 120.8 . . ? C29 C30 H30A 120.8 . . ? C32 C31 N7 115.05(14) . . ? C32 C31 H31A 108.5 . . ? N7 C31 H31A 108.5 . . ? C32 C31 H31B 108.5 . . ? N7 C31 H31B 108.5 . . ? H31A C31 H31B 107.5 . . ? 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 N7 115.42(14) . . ? C34 C33 H33A 108.4 . . ? N7 C33 H33A 108.4 . . ? C34 C33 H33B 108.4 . . ? N7 C33 H33B 108.4 . . ? H33A C33 H33B 107.5 . . ? C33 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C33 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C36 C35 N7 115.48(15) . . ? C36 C35 H35A 108.4 . . ? N7 C35 H35A 108.4 . . ? C36 C35 H35B 108.4 . . ? N7 C35 H35B 108.4 . . ? H35A C35 H35B 107.5 . . ? C35 C36 H36A 109.5 . . ? C35 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C35 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C38 C37 N7 115.24(16) . . ? C38 C37 H37A 108.5 . . ? N7 C37 H37A 108.5 . . ? C38 C37 H37B 108.5 . . ? N7 C37 H37B 108.5 . . ? H37A C37 H37B 107.5 . . ? C37 C38 H38A 109.5 . . ? C37 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C37 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? H1W O1W H2W 112.4 . . ? 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 C3 N3 C1 N1 -3.6(2) . . . . ? C3 N3 C1 O5 178.00(14) . . . . ? C2 N1 C1 N3 -0.1(3) . . . . ? C2 N1 C1 O5 178.34(15) . . . . ? C19 O5 C1 N3 0.0(2) . . . . ? C19 O5 C1 N1 -178.60(15) . . . . ? C1 N1 C2 N2 2.8(3) . . . . ? C1 N1 C2 O1 -176.71(15) . . . . ? C3 N2 C2 N1 -1.1(3) . . . . ? C3 N2 C2 O1 178.40(15) . . . . ? C4 O1 C2 N1 -177.26(16) . . . . ? C4 O1 C2 N2 3.2(2) . . . . ? C2 N2 C3 N3 -3.8(2) . . . . ? C2 N2 C3 O4 179.16(14) . . . . ? C1 N3 C3 N2 5.9(2) . . . . ? C1 N3 C3 O4 -176.92(13) . . . . ? C17 O4 C3 N2 -10.0(2) . . . . ? C17 O4 C3 N3 172.53(13) . . . . ? C2 O1 C4 C5 -105.54(19) . . . . ? C2 O1 C4 C9 79.8(2) . . . . ? C9 C4 C5 C6 0.1(3) . . . . ? O1 C4 C5 C6 -174.44(15) . . . . ? C4 C5 C6 C7 1.9(3) . . . . ? C5 C6 C7 C8 -2.4(3) . . . . ? C6 C7 C8 C9 1.0(3) . . . . ? C6 C7 C8 O2 174.88(15) . . . . ? C10 O2 C8 C7 117.34(18) . . . . ? C10 O2 C8 C9 -68.6(2) . . . . ? C7 C8 C9 C4 0.9(3) . . . . ? O2 C8 C9 C4 -172.95(14) . . . . ? C5 C4 C9 C8 -1.4(2) . . . . ? O1 C4 C9 C8 173.07(14) . . . . ? C11 N4 C10 N6 0.8(3) . . . . ? C11 N4 C10 O2 179.01(14) . . . . ? C12 N6 C10 N4 -0.8(2) . . . . ? C12 N6 C10 O2 -178.94(14) . . . . ? C8 O2 C10 N4 163.98(15) . . . . ? C8 O2 C10 N6 -17.6(2) . . . . ? C12 N5 C11 N4 4.4(2) . . . . ? C12 N5 C11 O6 -177.07(14) . . . . ? C10 N4 C11 N5 -2.8(2) . . . . ? C10 N4 C11 O6 178.60(14) . . . . ? C25 O6 C11 N5 17.2(2) . . . . ? C25 O6 C11 N4 -164.03(14) . . . . ? C11 N5 C12 N6 -4.5(2) . . . . ? C11 N5 C12 O3 177.92(13) . . . . ? C10 N6 C12 N5 2.9(2) . . . . ? C10 N6 C12 O3 -179.70(14) . . . . ? C13 O3 C12 N5 -170.04(13) . . . . ? C13 O3 C12 N6 12.1(2) . . . . ? C12 O3 C13 C18 65.94(19) . . . . ? C12 O3 C13 C14 -120.85(16) . . . . ? C18 C13 C14 C15 -1.4(2) . . . . ? O3 C13 C14 C15 -174.39(14) . . . . ? C13 C14 C15 C16 1.2(3) . . . . ? C14 C15 C16 C17 -0.3(2) . . . . ? C15 C16 C17 C18 -0.6(2) . . . . ? C15 C16 C17 O4 169.68(14) . . . . ? C3 O4 C17 C16 124.44(16) . . . . ? C3 O4 C17 C18 -65.1(2) . . . . ? C14 C13 C18 C17 0.5(2) . . . . ? O3 C13 C18 C17 173.27(13) . . . . ? C16 C17 C18 C13 0.5(2) . . . . ? O4 C17 C18 C13 -169.24(13) . . . . ? C1 O5 C19 C20 -67.6(2) . . . . ? C1 O5 C19 C24 117.95(18) . . . . ? C24 C19 C20 C21 -2.0(3) . . . . ? O5 C19 C20 C21 -176.04(16) . . . . ? C19 C20 C21 C22 1.3(3) . . . . ? C20 C21 C22 C23 0.5(3) . . . . ? C21 C22 C23 C24 -1.7(3) . . . . ? C20 C19 C24 C23 0.9(3) . . . . ? O5 C19 C24 C23 175.20(15) . . . . ? C22 C23 C24 C19 1.0(3) . . . . ? C11 O6 C25 C30 40.8(2) . . . . ? C11 O6 C25 C26 -145.49(16) . . . . ? C30 C25 C26 C27 -1.1(3) . . . . ? O6 C25 C26 C27 -174.87(15) . . . . ? C25 C26 C27 C28 -1.0(3) . . . . ? C26 C27 C28 C29 1.6(3) . . . . ? C27 C28 C29 C30 0.0(3) . . . . ? C26 C25 C30 C29 2.7(3) . . . . ? O6 C25 C30 C29 175.94(15) . . . . ? C28 C29 C30 C25 -2.1(3) . . . . ? C35 N7 C31 C32 59.8(2) . . . . ? C37 N7 C31 C32 -57.9(2) . . . . ? C33 N7 C31 C32 -178.41(17) . . . . ? C35 N7 C33 C34 -56.5(2) . . . . ? C31 N7 C33 C34 -178.44(17) . . . . ? C37 N7 C33 C34 61.3(2) . . . . ? C31 N7 C35 C36 58.82(19) . . . . ? C37 N7 C35 C36 179.60(15) . . . . ? C33 N7 C35 C36 -59.3(2) . . . . ? C35 N7 C37 C38 -173.34(16) . . . . ? C31 N7 C37 C38 -51.8(2) . . . . ? C33 N7 C37 C38 65.3(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 O1W H1W Cl1 0.84 2.29 3.123(2) 169.2 . O1W H2W Cl1 0.84 2.41 3.2445(19) 175.0 2_755 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.217 _refine_diff_density_min -0.208 _refine_diff_density_rms 0.040 # Attachment '5a-cl complex.pdf' # Attachment '5a.cif' data_sa191 _database_code_depnum_ccdc_archive 'CCDC 897876' #TrackingRef '5a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H18 N6 O6' _chemical_formula_sum 'C30 H18 N6 O6' _chemical_formula_weight 558.50 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M R-3 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 35.328(5) _cell_length_b 35.328(5) _cell_length_c 12.311(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 13307(4) _cell_formula_units_Z 18 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 11484 _cell_measurement_theta_min 1.9970 _cell_measurement_theta_max 27.4739 _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 1.255 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 5184 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8126 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'CrystalClear (Rigaku Inc., 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Saturn724+ CCD' _diffrn_measurement_method '\w scans at fixed \c = 45\%' _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19583 _diffrn_reflns_av_R_equivalents 0.0360 _diffrn_reflns_av_sigmaI/netI 0.0398 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 45 _diffrn_reflns_limit_k_min -45 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 27.47 _reflns_number_total 6750 _reflns_number_gt 5448 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_solution 'SHELX-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELX-97 (Sheldrick, 2008)' _computing_molecular_graphics ; Mercury: visualization and analysis of crystal structures, C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor, M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006. ; _computing_publication_material 'SHELX-97 (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0550P)^2^+13.7362P] 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 6750 _refine_ls_number_parameters 443 _refine_ls_number_restraints 184 _refine_ls_R_factor_all 0.0900 _refine_ls_R_factor_gt 0.0704 _refine_ls_wR_factor_ref 0.1669 _refine_ls_wR_factor_gt 0.1557 _refine_ls_goodness_of_fit_ref 1.178 _refine_ls_restrained_S_all 1.180 _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 O1 O 0.05021(5) 0.43178(5) 0.11872(12) 0.0435(4) Uani 1 1 d . . . O2 O 0.12503(5) 0.56842(5) -0.07786(12) 0.0460(4) Uani 1 1 d . . . O3 O 0.12052(5) 0.64274(5) 0.22433(11) 0.0421(4) Uani 1 1 d . A . O4 O 0.05646(6) 0.50869(5) 0.42608(12) 0.0474(4) Uani 1 1 d . A . O5 O 0.08162(8) 0.39549(7) 0.43991(14) 0.0709(6) Uani 1 1 d . . . N1 N 0.06604(7) 0.41354(7) 0.27876(15) 0.0481(5) Uani 1 1 d . . . N2 N 0.05236(6) 0.47311(6) 0.26613(14) 0.0401(4) Uani 1 1 d . . . N3 N 0.06895(7) 0.45325(7) 0.43760(15) 0.0464(5) Uani 1 1 d . . . N4 N 0.17209(6) 0.63989(6) -0.06164(14) 0.0419(4) Uani 1 1 d . A . N5 N 0.16987(6) 0.67775(6) 0.09577(15) 0.0433(4) Uani 1 1 d . A . N6 N 0.11856(6) 0.60160(6) 0.07631(14) 0.0385(4) Uani 1 1 d . A . C1 C 0.07169(9) 0.42222(8) 0.38434(19) 0.0490(6) Uani 1 1 d . . . C2 C 0.05643(7) 0.44061(7) 0.22499(17) 0.0414(5) Uani 1 1 d . . . C3 C 0.05939(7) 0.47742(7) 0.37210(17) 0.0409(5) Uani 1 1 d . . . C4 C 0.05009(7) 0.46263(7) 0.04573(17) 0.0384(5) Uani 1 1 d . . . C5 C 0.01303(8) 0.44946(8) -0.01526(18) 0.0435(5) Uani 1 1 d . . . H5 H -0.0116 0.4222 -0.0039 0.052 Uiso 1 1 calc R . . C6 C 0.01305(8) 0.47750(8) -0.09410(19) 0.0476(6) Uani 1 1 d . . . H6 H -0.0120 0.4694 -0.1349 0.057 Uiso 1 1 calc R . . C7 C 0.05009(8) 0.51747(8) -0.11232(18) 0.0456(5) Uani 1 1 d . . . H7 H 0.0504 0.5362 -0.1660 0.055 Uiso 1 1 calc R . . C8 C 0.08653(7) 0.52905(7) -0.04932(17) 0.0390(5) Uani 1 1 d . . . C9 C 0.08774(7) 0.50255(7) 0.03072(16) 0.0388(5) Uani 1 1 d . . . H9 H 0.1126 0.5110 0.0727 0.047 Uiso 1 1 calc R . . C10 C 0.13867(7) 0.60437(7) -0.01688(16) 0.0380(5) Uani 1 1 d . . . C11 C 0.18518(7) 0.67504(7) -0.00046(18) 0.0426(5) Uani 1 1 d D . . C12 C 0.13658(7) 0.63974(7) 0.12826(17) 0.0377(5) Uani 1 1 d . . . C13 C 0.08353(7) 0.60626(7) 0.26864(16) 0.0380(5) Uani 1 1 d . . . C14 C 0.04502(7) 0.60735(7) 0.27344(17) 0.0411(5) Uani 1 1 d . A . H14 H 0.0429 0.6301 0.2415 0.049 Uiso 1 1 calc R . . C15 C 0.00971(8) 0.57394(8) 0.32666(18) 0.0445(5) Uani 1 1 d . . . H15 H -0.0164 0.5742 0.3308 0.053 Uiso 1 1 calc R A . C16 C 0.01278(8) 0.53984(8) 0.37420(17) 0.0430(5) Uani 1 1 d . A . H16 H -0.0110 0.5172 0.4099 0.052 Uiso 1 1 calc R . . C17 C 0.05194(8) 0.54059(7) 0.36689(16) 0.0402(5) Uani 1 1 d . . . C18 C 0.08801(7) 0.57319(7) 0.31496(17) 0.0405(5) Uani 1 1 d . A . H18 H 0.1142 0.5729 0.3113 0.049 Uiso 1 1 calc R . . C19 C 0.08828(11) 0.40148(10) 0.5530(2) 0.0615(8) Uani 1 1 d . . . C20 C 0.12804(13) 0.43250(13) 0.5938(3) 0.0846(10) Uani 1 1 d . . . H20 H 0.1503 0.4509 0.5469 0.102 Uiso 1 1 calc R . . C21 C 0.13482(14) 0.43625(14) 0.7045(3) 0.0967(12) Uani 1 1 d . . . H21 H 0.1616 0.4573 0.7326 0.116 Uiso 1 1 calc R . . C22 C 0.10203(14) 0.40901(13) 0.7726(3) 0.0854(10) Uani 1 1 d . . . H22 H 0.1065 0.4116 0.8473 0.103 Uiso 1 1 calc R . . C23 C 0.06262(12) 0.37792(12) 0.7316(2) 0.0750(9) Uani 1 1 d . . . H23 H 0.0405 0.3595 0.7790 0.090 Uiso 1 1 calc R . . C24 C 0.05512(11) 0.37344(10) 0.6198(2) 0.0649(8) Uani 1 1 d . . . H24 H 0.0285 0.3521 0.5917 0.078 Uiso 1 1 calc R . . O6 O 0.2209(4) 0.7131(3) -0.0286(11) 0.047(2) Uani 0.540(19) 1 d PDU A 1 C25 C 0.2380(4) 0.7184(6) -0.1340(10) 0.054(2) Uani 0.540(19) 1 d PDU A 1 C30 C 0.2761(3) 0.7170(4) -0.1430(8) 0.074(2) Uani 0.540(19) 1 d PDU A 1 H30 H 0.2868 0.7090 -0.0837 0.088 Uiso 0.540(19) 1 calc PR A 1 C26 C 0.2216(4) 0.7293(3) -0.2221(7) 0.062(2) Uani 0.540(19) 1 d PDU A 1 H26 H 0.1957 0.7299 -0.2159 0.074 Uiso 0.540(19) 1 calc PR A 1 C27 C 0.2439(4) 0.7396(3) -0.3211(7) 0.067(2) Uani 0.540(19) 1 d PDU A 1 H27 H 0.2323 0.7459 -0.3818 0.081 Uiso 0.540(19) 1 calc PR A 1 C28 C 0.2831(4) 0.7403(3) -0.3281(8) 0.070(3) Uani 0.540(19) 1 d PDU A 1 H28 H 0.2993 0.7494 -0.3920 0.084 Uiso 0.540(19) 1 calc PR A 1 C29 C 0.2985(3) 0.7277(4) -0.2411(8) 0.083(3) Uani 0.540(19) 1 d PDU A 1 H29 H 0.3239 0.7262 -0.2478 0.100 Uiso 0.540(19) 1 calc PR A 1 O6' O 0.2142(5) 0.7145(4) -0.0428(13) 0.047(3) Uani 0.460(19) 1 d PDU A 2 C25' C 0.2315(4) 0.7196(7) -0.1475(11) 0.047(2) Uani 0.460(19) 1 d PDU A 2 C26' C 0.2056(4) 0.7207(4) -0.2290(8) 0.058(2) Uani 0.460(19) 1 d PDU A 2 H26A H 0.1771 0.7140 -0.2154 0.069 Uiso 0.460(19) 1 calc PR A 2 C27' C 0.2234(5) 0.7319(4) -0.3324(8) 0.064(2) Uani 0.460(19) 1 d PDU A 2 H27A H 0.2066 0.7326 -0.3898 0.077 Uiso 0.460(19) 1 calc PR A 2 C28' C 0.2661(4) 0.7420(3) -0.3501(9) 0.063(3) Uani 0.460(19) 1 d PDU A 2 H28A H 0.2778 0.7498 -0.4196 0.076 Uiso 0.460(19) 1 calc PR A 2 C29' C 0.2914(3) 0.7409(4) -0.2678(9) 0.074(3) Uani 0.460(19) 1 d PDU A 2 H29A H 0.3199 0.7474 -0.2815 0.089 Uiso 0.460(19) 1 calc PR A 2 C30' C 0.2742(4) 0.7298(4) -0.1628(9) 0.069(3) Uani 0.460(19) 1 d PDU A 2 H30A H 0.2911 0.7294 -0.1053 0.083 Uiso 0.460(19) 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0563(10) 0.0431(8) 0.0358(8) 0.0046(7) 0.0045(7) 0.0284(8) O2 0.0546(10) 0.0376(8) 0.0351(8) 0.0000(6) 0.0104(7) 0.0151(7) O3 0.0506(9) 0.0386(8) 0.0340(8) 0.0016(6) 0.0101(7) 0.0198(7) O4 0.0724(11) 0.0512(9) 0.0318(8) 0.0097(7) 0.0117(7) 0.0409(9) O5 0.1277(18) 0.0873(14) 0.0406(10) 0.0158(9) 0.0130(10) 0.0860(14) N1 0.0659(13) 0.0527(12) 0.0386(10) 0.0094(9) 0.0115(9) 0.0393(11) N2 0.0481(11) 0.0435(10) 0.0345(9) 0.0060(8) 0.0078(8) 0.0272(9) N3 0.0628(13) 0.0549(12) 0.0359(10) 0.0113(9) 0.0109(9) 0.0401(11) N4 0.0478(11) 0.0395(10) 0.0343(9) 0.0031(8) 0.0073(8) 0.0188(9) N5 0.0480(11) 0.0394(10) 0.0374(10) 0.0002(8) 0.0059(8) 0.0181(9) N6 0.0449(10) 0.0379(10) 0.0326(9) 0.0016(7) 0.0032(8) 0.0206(8) C1 0.0668(16) 0.0560(14) 0.0392(12) 0.0151(11) 0.0121(11) 0.0419(13) C2 0.0464(12) 0.0438(12) 0.0360(11) 0.0090(9) 0.0099(10) 0.0241(10) C3 0.0484(13) 0.0446(12) 0.0366(11) 0.0095(9) 0.0123(10) 0.0285(11) C4 0.0482(13) 0.0397(11) 0.0316(10) 0.0042(9) 0.0044(9) 0.0252(10) C5 0.0464(13) 0.0414(12) 0.0385(12) -0.0027(9) 0.0014(10) 0.0188(10) C6 0.0532(14) 0.0511(14) 0.0378(12) -0.0039(10) -0.0070(10) 0.0258(12) C7 0.0598(15) 0.0466(13) 0.0308(11) 0.0018(10) 0.0007(10) 0.0269(12) C8 0.0433(12) 0.0359(11) 0.0321(10) -0.0017(9) 0.0053(9) 0.0157(10) C9 0.0422(12) 0.0426(12) 0.0317(10) -0.0001(9) 0.0001(9) 0.0213(10) C10 0.0450(12) 0.0391(11) 0.0298(10) 0.0022(9) 0.0031(9) 0.0210(10) C11 0.0446(12) 0.0392(12) 0.0375(11) 0.0040(9) 0.0052(10) 0.0161(10) C12 0.0420(12) 0.0401(11) 0.0332(10) 0.0025(9) 0.0045(9) 0.0220(10) C13 0.0485(13) 0.0387(11) 0.0266(10) 0.0015(8) 0.0058(9) 0.0217(10) C14 0.0526(13) 0.0434(12) 0.0334(11) 0.0024(9) 0.0016(10) 0.0287(11) C15 0.0466(13) 0.0529(14) 0.0395(12) 0.0012(10) 0.0044(10) 0.0290(11) C16 0.0493(13) 0.0466(13) 0.0336(11) 0.0062(9) 0.0093(10) 0.0245(11) C17 0.0583(14) 0.0430(12) 0.0281(10) 0.0048(9) 0.0063(10) 0.0319(11) C18 0.0475(12) 0.0483(13) 0.0328(11) 0.0023(9) 0.0061(9) 0.0293(11) C19 0.096(2) 0.0789(19) 0.0415(13) 0.0196(13) 0.0135(14) 0.0678(19) C20 0.085(2) 0.113(3) 0.0625(19) 0.0323(19) 0.0172(18) 0.055(2) C21 0.094(3) 0.121(3) 0.065(2) 0.029(2) -0.0032(19) 0.047(2) C22 0.108(3) 0.108(3) 0.0497(17) 0.0226(18) -0.0033(18) 0.062(2) C23 0.094(2) 0.093(2) 0.0522(17) 0.0323(16) 0.0207(17) 0.057(2) C24 0.086(2) 0.0729(19) 0.0539(16) 0.0173(14) 0.0085(15) 0.0535(17) O6 0.049(4) 0.039(3) 0.038(3) 0.003(2) 0.010(3) 0.011(2) C25 0.055(4) 0.042(3) 0.049(4) 0.004(3) 0.012(3) 0.012(3) C30 0.068(4) 0.075(5) 0.064(4) 0.009(3) 0.016(3) 0.024(3) C26 0.067(4) 0.056(4) 0.056(4) 0.003(3) 0.009(3) 0.026(3) C27 0.073(5) 0.062(4) 0.057(3) 0.002(3) 0.010(4) 0.026(4) C28 0.071(5) 0.062(3) 0.053(4) 0.003(3) 0.019(4) 0.016(3) C29 0.071(4) 0.086(5) 0.071(4) 0.011(3) 0.030(3) 0.024(3) O6' 0.053(5) 0.040(3) 0.038(4) 0.004(2) 0.006(3) 0.014(3) C25' 0.060(4) 0.037(3) 0.038(4) 0.004(3) 0.015(3) 0.019(3) C26' 0.063(5) 0.055(4) 0.050(4) 0.006(3) 0.014(3) 0.026(4) C27' 0.074(5) 0.059(4) 0.055(4) 0.010(3) 0.014(4) 0.030(4) C28' 0.066(5) 0.057(4) 0.058(4) 0.015(3) 0.024(4) 0.024(4) C29' 0.068(4) 0.073(5) 0.068(5) 0.013(4) 0.022(4) 0.025(3) C30' 0.065(4) 0.062(5) 0.063(4) 0.011(3) 0.013(3) 0.019(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C2 1.337(3) . ? O1 C4 1.414(2) . ? O2 C10 1.340(3) . ? O2 C8 1.420(3) . ? O3 C12 1.339(2) . ? O3 C13 1.408(3) . ? O4 C3 1.337(3) . ? O4 C17 1.416(3) . ? O5 C1 1.347(3) . ? O5 C19 1.410(3) . ? N1 C1 1.328(3) . ? N1 C2 1.339(3) . ? N2 C3 1.323(3) . ? N2 C2 1.327(3) . ? N3 C1 1.322(3) . ? N3 C3 1.335(3) . ? N4 C11 1.322(3) . ? N4 C10 1.338(3) . ? N5 C11 1.326(3) . ? N5 C12 1.329(3) . ? N6 C10 1.327(3) . ? N6 C12 1.331(3) . ? C4 C5 1.373(3) . ? C4 C9 1.384(3) . ? C5 C6 1.387(3) . ? C5 H5 0.9300 . ? C6 C7 1.381(3) . ? C6 H6 0.9300 . ? C7 C8 1.378(3) . ? C7 H7 0.9300 . ? C8 C9 1.375(3) . ? C9 H9 0.9300 . ? C11 O6 1.351(7) . ? C11 O6' 1.356(8) . ? C13 C18 1.378(3) . ? C13 C14 1.381(3) . ? C14 C15 1.381(3) . ? C14 H14 0.9300 . ? C15 C16 1.392(3) . ? C15 H15 0.9300 . ? C16 C17 1.373(3) . ? C16 H16 0.9300 . ? C17 C18 1.375(3) . ? C18 H18 0.9300 . ? C19 C24 1.367(4) . ? C19 C20 1.374(5) . ? C20 C21 1.379(5) . ? C20 H20 0.9300 . ? C21 C22 1.362(5) . ? C21 H21 0.9300 . ? C22 C23 1.367(5) . ? C22 H22 0.9300 . ? C23 C24 1.397(4) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? O6 C25 1.405(7) . ? C25 C26 1.373(8) . ? C25 C30 1.373(8) . ? C30 C29 1.388(8) . ? C30 H30 0.9300 . ? C26 C27 1.397(8) . ? C26 H26 0.9300 . ? C27 C28 1.375(8) . ? C27 H27 0.9300 . ? C28 C29 1.373(8) . ? C28 H28 0.9300 . ? C29 H29 0.9300 . ? O6' C25' 1.400(8) . ? C25' C26' 1.371(8) . ? C25' C30' 1.378(8) . ? C26' C27' 1.387(8) . ? C26' H26A 0.9300 . ? C27' C28' 1.382(8) . ? C27' H27A 0.9300 . ? C28' C29' 1.366(8) . ? C28' H28A 0.9300 . ? C29' C30' 1.398(8) . ? C29' H29A 0.9300 . ? C30' H30A 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 O1 C4 120.35(17) . . ? C10 O2 C8 120.26(16) . . ? C12 O3 C13 120.40(16) . . ? C3 O4 C17 119.19(16) . . ? C1 O5 C19 118.6(2) . . ? C1 N1 C2 112.43(19) . . ? C3 N2 C2 112.38(18) . . ? C1 N3 C3 112.20(19) . . ? C11 N4 C10 112.11(18) . . ? C11 N5 C12 112.51(19) . . ? C10 N6 C12 111.92(18) . . ? N3 C1 N1 127.8(2) . . ? N3 C1 O5 118.8(2) . . ? N1 C1 O5 113.4(2) . . ? N2 C2 O1 119.94(19) . . ? N2 C2 N1 127.2(2) . . ? O1 C2 N1 112.81(19) . . ? N2 C3 N3 128.0(2) . . ? N2 C3 O4 119.86(19) . . ? N3 C3 O4 112.16(19) . . ? C5 C4 C9 122.7(2) . . ? C5 C4 O1 117.14(19) . . ? C9 C4 O1 119.89(19) . . ? C4 C5 C6 118.7(2) . . ? C4 C5 H5 120.6 . . ? C6 C5 H5 120.6 . . ? C7 C6 C5 120.4(2) . . ? C7 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? C8 C7 C6 118.6(2) . . ? C8 C7 H7 120.7 . . ? C6 C7 H7 120.7 . . ? C9 C8 C7 122.9(2) . . ? C9 C8 O2 120.2(2) . . ? C7 C8 O2 116.53(19) . . ? C8 C9 C4 116.6(2) . . ? C8 C9 H9 121.7 . . ? C4 C9 H9 121.7 . . ? N6 C10 N4 127.9(2) . . ? N6 C10 O2 119.26(19) . . ? N4 C10 O2 112.86(18) . . ? N4 C11 N5 127.8(2) . . ? N4 C11 O6 120.2(7) . . ? N5 C11 O6 111.6(6) . . ? N4 C11 O6' 118.5(8) . . ? N5 C11 O6' 113.3(8) . . ? O6 C11 O6' 13.4(15) . . ? N5 C12 N6 127.71(19) . . ? N5 C12 O3 112.45(18) . . ? N6 C12 O3 119.83(19) . . ? C18 C13 C14 122.6(2) . . ? C18 C13 O3 119.3(2) . . ? C14 C13 O3 117.85(19) . . ? C15 C14 C13 118.5(2) . . ? C15 C14 H14 120.7 . . ? C13 C14 H14 120.7 . . ? C14 C15 C16 120.8(2) . . ? C14 C15 H15 119.6 . . ? C16 C15 H15 119.6 . . ? C17 C16 C15 118.0(2) . . ? C17 C16 H16 121.0 . . ? C15 C16 H16 121.0 . . ? C16 C17 C18 123.3(2) . . ? C16 C17 O4 117.65(19) . . ? C18 C17 O4 118.7(2) . . ? C17 C18 C13 116.8(2) . . ? C17 C18 H18 121.6 . . ? C13 C18 H18 121.6 . . ? C24 C19 C20 121.5(3) . . ? C24 C19 O5 117.8(3) . . ? C20 C19 O5 120.6(3) . . ? C19 C20 C21 119.8(3) . . ? C19 C20 H20 120.1 . . ? C21 C20 H20 120.1 . . ? C22 C21 C20 119.7(4) . . ? C22 C21 H21 120.2 . . ? C20 C21 H21 120.2 . . ? C21 C22 C23 120.4(3) . . ? C21 C22 H22 119.8 . . ? C23 C22 H22 119.8 . . ? C22 C23 C24 120.9(3) . . ? C22 C23 H23 119.5 . . ? C24 C23 H23 119.5 . . ? C19 C24 C23 117.8(3) . . ? C19 C24 H24 121.1 . . ? C23 C24 H24 121.1 . . ? C11 O6 C25 119.7(11) . . ? C26 C25 C30 120.3(10) . . ? C26 C25 O6 123.5(11) . . ? C30 C25 O6 115.8(10) . . ? C25 C30 C29 119.7(9) . . ? C25 C30 H30 120.1 . . ? C29 C30 H30 120.1 . . ? C25 C26 C27 120.0(9) . . ? C25 C26 H26 120.0 . . ? C27 C26 H26 120.0 . . ? C28 C27 C26 119.4(7) . . ? C28 C27 H27 120.3 . . ? C26 C27 H27 120.3 . . ? C29 C28 C27 120.2(7) . . ? C29 C28 H28 119.9 . . ? C27 C28 H28 119.9 . . ? C28 C29 C30 120.2(8) . . ? C28 C29 H29 119.9 . . ? C30 C29 H29 119.9 . . ? C11 O6' C25' 122.9(13) . . ? C26' C25' C30' 123.4(11) . . ? C26' C25' O6' 115.0(11) . . ? C30' C25' O6' 120.7(11) . . ? C25' C26' C27' 117.9(9) . . ? C25' C26' H26A 121.1 . . ? C27' C26' H26A 121.1 . . ? C28' C27' C26' 119.8(8) . . ? C28' C27' H27A 120.1 . . ? C26' C27' H27A 120.1 . . ? C29' C28' C27' 121.4(8) . . ? C29' C28' H28A 119.3 . . ? C27' C28' H28A 119.3 . . ? C28' C29' C30' 119.7(9) . . ? C28' C29' H29A 120.2 . . ? C30' C29' H29A 120.2 . . ? C25' C30' C29' 117.7(10) . . ? C25' C30' H30A 121.1 . . ? C29' C30' H30A 121.1 . . ? 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 C3 N3 C1 N1 -0.2(4) . . . . ? C3 N3 C1 O5 179.3(2) . . . . ? C2 N1 C1 N3 -0.1(4) . . . . ? C2 N1 C1 O5 -179.7(2) . . . . ? C19 O5 C1 N3 0.6(4) . . . . ? C19 O5 C1 N1 -179.9(2) . . . . ? C3 N2 C2 O1 179.8(2) . . . . ? C3 N2 C2 N1 0.6(3) . . . . ? C4 O1 C2 N2 15.8(3) . . . . ? C4 O1 C2 N1 -164.97(19) . . . . ? C1 N1 C2 N2 -0.1(4) . . . . ? C1 N1 C2 O1 -179.3(2) . . . . ? C2 N2 C3 N3 -1.0(3) . . . . ? C2 N2 C3 O4 -179.9(2) . . . . ? C1 N3 C3 N2 0.8(4) . . . . ? C1 N3 C3 O4 179.8(2) . . . . ? C17 O4 C3 N2 -8.8(3) . . . . ? C17 O4 C3 N3 172.2(2) . . . . ? C2 O1 C4 C5 -121.5(2) . . . . ? C2 O1 C4 C9 64.6(3) . . . . ? C9 C4 C5 C6 -0.9(3) . . . . ? O1 C4 C5 C6 -174.67(19) . . . . ? C4 C5 C6 C7 1.5(3) . . . . ? C5 C6 C7 C8 -1.1(3) . . . . ? C6 C7 C8 C9 0.2(3) . . . . ? C6 C7 C8 O2 174.1(2) . . . . ? C10 O2 C8 C9 -80.1(3) . . . . ? C10 O2 C8 C7 105.9(2) . . . . ? C7 C8 C9 C4 0.4(3) . . . . ? O2 C8 C9 C4 -173.33(18) . . . . ? C5 C4 C9 C8 0.0(3) . . . . ? O1 C4 C9 C8 173.59(18) . . . . ? C12 N6 C10 N4 -2.3(3) . . . . ? C12 N6 C10 O2 178.50(19) . . . . ? C11 N4 C10 N6 0.9(3) . . . . ? C11 N4 C10 O2 -179.92(19) . . . . ? C8 O2 C10 N6 7.1(3) . . . . ? C8 O2 C10 N4 -172.22(19) . . . . ? C10 N4 C11 N5 1.7(3) . . . . ? C10 N4 C11 O6 174.6(9) . . . . ? C10 N4 C11 O6' -170.1(10) . . . . ? C12 N5 C11 N4 -2.2(4) . . . . ? C12 N5 C11 O6 -175.7(8) . . . . ? C12 N5 C11 O6' 169.9(10) . . . . ? C11 N5 C12 N6 0.4(3) . . . . ? C11 N5 C12 O3 -178.60(19) . . . . ? C10 N6 C12 N5 1.6(3) . . . . ? C10 N6 C12 O3 -179.46(19) . . . . ? C13 O3 C12 N5 176.35(18) . . . . ? C13 O3 C12 N6 -2.7(3) . . . . ? C12 O3 C13 C18 76.0(3) . . . . ? C12 O3 C13 C14 -110.4(2) . . . . ? C18 C13 C14 C15 -0.1(3) . . . . ? O3 C13 C14 C15 -173.43(19) . . . . ? C13 C14 C15 C16 -0.2(3) . . . . ? C14 C15 C16 C17 0.3(3) . . . . ? C15 C16 C17 C18 -0.1(3) . . . . ? C15 C16 C17 O4 172.8(2) . . . . ? C3 O4 C17 C16 111.5(2) . . . . ? C3 O4 C17 C18 -75.3(3) . . . . ? C16 C17 C18 C13 -0.1(3) . . . . ? O4 C17 C18 C13 -172.92(19) . . . . ? C14 C13 C18 C17 0.2(3) . . . . ? O3 C13 C18 C17 173.47(18) . . . . ? C1 O5 C19 C24 102.0(3) . . . . ? C1 O5 C19 C20 -82.7(4) . . . . ? C24 C19 C20 C21 -1.1(5) . . . . ? O5 C19 C20 C21 -176.2(3) . . . . ? C19 C20 C21 C22 0.2(6) . . . . ? C20 C21 C22 C23 0.4(6) . . . . ? C21 C22 C23 C24 -0.1(5) . . . . ? C20 C19 C24 C23 1.3(4) . . . . ? O5 C19 C24 C23 176.6(2) . . . . ? C22 C23 C24 C19 -0.8(5) . . . . ? N4 C11 O6 C25 14.7(17) . . . . ? N5 C11 O6 C25 -171.3(11) . . . . ? O6' C11 O6 C25 -72(6) . . . . ? C11 O6 C25 C26 82(2) . . . . ? C11 O6 C25 C30 -105.7(16) . . . . ? C26 C25 C30 C29 1(2) . . . . ? O6 C25 C30 C29 -171.4(11) . . . . ? C30 C25 C26 C27 -1(2) . . . . ? O6 C25 C26 C27 171.5(12) . . . . ? C25 C26 C27 C28 -2.5(15) . . . . ? C26 C27 C28 C29 5.2(12) . . . . ? C27 C28 C29 C30 -4.5(12) . . . . ? C25 C30 C29 C28 1.2(15) . . . . ? N4 C11 O6' C25' -1(2) . . . . ? N5 C11 O6' C25' -174.3(13) . . . . ? O6 C11 O6' C25' 100(7) . . . . ? C11 O6' C25' C26' 83(2) . . . . ? C11 O6' C25' C30' -107.0(19) . . . . ? C30' C25' C26' C27' 1(2) . . . . ? O6' C25' C26' C27' 170.8(13) . . . . ? C25' C26' C27' C28' -0.7(16) . . . . ? C26' C27' C28' C29' 0.6(15) . . . . ? C27' C28' C29' C30' -0.9(15) . . . . ? C26' C25' C30' C29' -1(2) . . . . ? O6' C25' C30' C29' -170.5(13) . . . . ? C28' C29' C30' C25' 1.3(17) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.184 _refine_diff_density_min -0.213 _refine_diff_density_rms 0.040 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.000 -0.015 672 75 ' ' 2 0.333 0.667 1.147 671 76 ' ' 3 0.667 0.333 0.814 671 76 ' ' _platon_squeeze_details ; ;