# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Anne Petitjean' _publ_contact_author_email anne.petitjean@chem.queensu.ca loop_ _publ_author_name 'Weiwen Zhao' 'Ruiyao Wang' 'Anne Petitjean' # Attachment 'web_deposit_cif_file_2_AnnePetitjean_1307027851.ap21.cif' data_ap21 _database_code_depnum_ccdc_archive 'CCDC 828090' #TrackingRef 'web_deposit_cif_file_2_AnnePetitjean_1307027851.ap21.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H13 N3 O2' _chemical_formula_weight 255.27 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.7004(12) _cell_length_b 15.9776(13) _cell_length_c 7.1602(6) _cell_angle_alpha 90.00 _cell_angle_beta 107.250(5) _cell_angle_gamma 90.00 _cell_volume 1278.3(2) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 1585 _cell_measurement_theta_min 2.22 _cell_measurement_theta_max 26.40 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.326 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9730 _exptl_absorpt_correction_T_max 0.9963 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 5323 _diffrn_reflns_av_R_equivalents 0.0217 _diffrn_reflns_av_sigmaI/netI 0.0339 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2469 _reflns_number_gt 1731 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0482P)^2^+0.4026P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0067(16) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2469 _refine_ls_number_parameters 162 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0717 _refine_ls_R_factor_gt 0.0441 _refine_ls_wR_factor_ref 0.1172 _refine_ls_wR_factor_gt 0.1017 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.22365(13) 0.26662(9) -0.0395(2) 0.0310(4) Uani 1 1 d . . . N2 N 0.37404(14) 0.14838(9) 0.1424(2) 0.0324(4) Uani 1 1 d . . . H2B H 0.3071 0.1410 0.0472 0.039 Uiso 1 1 calc R . . O1 O 0.49913(11) 0.24464(8) 0.33203(19) 0.0404(4) Uani 1 1 d . . . C1 C 0.14663(17) 0.32482(12) -0.1339(3) 0.0372(5) Uani 1 1 d . . . H1A H 0.0768 0.3072 -0.2324 0.045 Uiso 1 1 calc R . . C2 C 0.16289(18) 0.40946(12) -0.0961(3) 0.0413(5) Uani 1 1 d . . . H2A H 0.1051 0.4487 -0.1666 0.050 Uiso 1 1 calc R . . C3 C 0.26340(18) 0.43605(12) 0.0443(3) 0.0405(5) Uani 1 1 d . . . H3A H 0.2764 0.4940 0.0728 0.049 Uiso 1 1 calc R . . C4 C 0.34591(17) 0.37723(11) 0.1441(3) 0.0344(4) Uani 1 1 d . . . H4A H 0.4169 0.3937 0.2416 0.041 Uiso 1 1 calc R . . C5 C 0.32163(15) 0.29370(11) 0.0973(2) 0.0281(4) Uani 1 1 d . . . C6 C 0.40773(16) 0.22807(11) 0.2021(3) 0.0299(4) Uani 1 1 d . . . C7 C 0.43953(17) 0.07905(12) 0.2236(3) 0.0387(5) Uani 1 1 d . . . H7A H 0.5117 0.0884 0.3255 0.046 Uiso 1 1 calc R . . N3 N 0.41195(16) 0.00332(10) 0.1742(3) 0.0445(4) Uani 1 1 d . . . O2 O 0.30452(14) 0.00115(8) 0.0183(2) 0.0512(4) Uani 1 1 d . . . C8 C 0.2657(2) -0.08510(13) -0.0134(3) 0.0572(7) Uani 1 1 d . . . H8A H 0.3355 -0.1211 -0.0076 0.069 Uiso 1 1 calc R . . H8B H 0.2080 -0.0907 -0.1455 0.069 Uiso 1 1 calc R . . C9 C 0.20714(12) -0.11482(8) 0.13786(18) 0.0385(5) Uani 1 1 d G . . C10 C 0.27697(11) -0.15219(8) 0.30688(18) 0.0354(5) Uani 1 1 d G . . H10A H 0.3602 -0.1598 0.3265 0.042 Uiso 1 1 calc R . . C11 C 0.22593(12) -0.17846(8) 0.44744(19) 0.0433(5) Uani 1 1 d G . . H11A H 0.2740 -0.2042 0.5639 0.052 Uiso 1 1 calc R . . C12 C 0.10505(13) -0.16737(9) 0.4190(2) 0.0563(6) Uani 1 1 d G . . H12A H 0.0699 -0.1855 0.5158 0.068 Uiso 1 1 calc R . . C13 C 0.03522(12) -0.13000(9) 0.2499(3) 0.0641(7) Uani 1 1 d G . . H13A H -0.0480 -0.1224 0.2303 0.077 Uiso 1 1 calc R . . C14 C 0.08626(13) -0.10373(9) 0.1094(2) 0.0563(6) Uani 1 1 d G . . H14A H 0.0382 -0.0780 -0.0070 0.068 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0334(8) 0.0294(8) 0.0306(8) 0.0006(7) 0.0098(7) -0.0008(7) N2 0.0371(8) 0.0266(8) 0.0319(8) 0.0029(7) 0.0076(7) 0.0022(6) O1 0.0345(7) 0.0426(8) 0.0395(8) 0.0041(6) 0.0040(7) -0.0032(6) C1 0.0377(10) 0.0362(11) 0.0350(11) 0.0015(9) 0.0068(9) 0.0030(8) C2 0.0472(12) 0.0354(11) 0.0401(11) 0.0079(9) 0.0109(10) 0.0077(9) C3 0.0567(13) 0.0245(10) 0.0435(12) 0.0010(9) 0.0197(11) -0.0013(9) C4 0.0419(11) 0.0297(10) 0.0326(10) -0.0014(8) 0.0124(9) -0.0053(8) C5 0.0333(10) 0.0279(10) 0.0254(9) 0.0019(7) 0.0123(8) -0.0024(7) C6 0.0318(10) 0.0317(10) 0.0282(9) 0.0015(8) 0.0121(9) -0.0024(8) C7 0.0420(11) 0.0318(11) 0.0437(12) 0.0062(9) 0.0149(9) 0.0066(8) N3 0.0537(11) 0.0352(10) 0.0447(10) 0.0055(8) 0.0149(9) 0.0074(8) O2 0.0827(11) 0.0291(8) 0.0362(8) 0.0049(6) 0.0089(8) -0.0047(7) C8 0.104(2) 0.0309(12) 0.0335(11) -0.0036(9) 0.0158(12) -0.0079(12) C9 0.0555(13) 0.0187(9) 0.0354(11) -0.0068(8) 0.0041(9) -0.0004(9) C10 0.0399(11) 0.0260(10) 0.0387(11) -0.0022(8) 0.0091(9) 0.0012(8) C11 0.0541(13) 0.0309(11) 0.0453(12) 0.0008(9) 0.0151(10) -0.0028(9) C12 0.0571(14) 0.0446(13) 0.0738(17) -0.0106(12) 0.0295(13) -0.0125(11) C13 0.0364(12) 0.0498(15) 0.102(2) -0.0243(15) 0.0134(14) -0.0051(10) C14 0.0572(14) 0.0323(12) 0.0588(15) -0.0107(11) -0.0147(12) 0.0054(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 N1 C1 1.331(2) . ? N1 C5 1.340(2) . ? N2 C6 1.364(2) . ? N2 C7 1.374(2) . ? N2 H2B 0.8800 . ? O1 C6 1.220(2) . ? C1 C2 1.381(3) . ? C1 H1A 0.9500 . ? C2 C3 1.368(3) . ? C2 H2A 0.9500 . ? C3 C4 1.384(3) . ? C3 H3A 0.9500 . ? C4 C5 1.385(2) . ? C4 H4A 0.9500 . ? C5 C6 1.493(2) . ? C7 N3 1.275(2) . ? C7 H7A 0.9500 . ? N3 O2 1.412(2) . ? O2 C8 1.448(2) . ? C8 C9 1.519(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C14 1.3792 . ? C9 C10 1.3793 . ? C10 C11 1.3792 . ? C10 H10A 0.9500 . ? C11 C12 1.3793 . ? C11 H11A 0.9500 . ? C12 C13 1.3793 . ? C12 H12A 0.9500 . ? C13 C14 1.3792 . ? C13 H13A 0.9500 . ? C14 H14A 0.9500 . ? 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 C1 N1 C5 116.69(16) . . ? C6 N2 C7 123.14(16) . . ? C6 N2 H2B 118.4 . . ? C7 N2 H2B 118.4 . . ? N1 C1 C2 123.46(18) . . ? N1 C1 H1A 118.3 . . ? C2 C1 H1A 118.3 . . ? C3 C2 C1 119.10(18) . . ? C3 C2 H2A 120.5 . . ? C1 C2 H2A 120.5 . . ? C2 C3 C4 118.96(18) . . ? C2 C3 H3A 120.5 . . ? C4 C3 H3A 120.5 . . ? C3 C4 C5 117.88(18) . . ? C3 C4 H4A 121.1 . . ? C5 C4 H4A 121.1 . . ? N1 C5 C4 123.91(17) . . ? N1 C5 C6 116.37(15) . . ? C4 C5 C6 119.72(16) . . ? O1 C6 N2 123.25(17) . . ? O1 C6 C5 122.61(16) . . ? N2 C6 C5 114.13(15) . . ? N3 C7 N2 125.74(19) . . ? N3 C7 H7A 117.1 . . ? N2 C7 H7A 117.1 . . ? C7 N3 O2 109.59(16) . . ? N3 O2 C8 108.16(15) . . ? O2 C8 C9 111.89(16) . . ? O2 C8 H8A 109.2 . . ? C9 C8 H8A 109.2 . . ? O2 C8 H8B 109.2 . . ? C9 C8 H8B 109.2 . . ? H8A C8 H8B 107.9 . . ? C14 C9 C10 120.0 . . ? C14 C9 C8 120.92(13) . . ? C10 C9 C8 119.07(13) . . ? C11 C10 C9 120.0 . . ? C11 C10 H10A 120.0 . . ? C9 C10 H10A 120.0 . . ? C10 C11 C12 120.0 . . ? C10 C11 H11A 120.0 . . ? C12 C11 H11A 120.0 . . ? C11 C12 C13 120.0 . . ? C11 C12 H12A 120.0 . . ? C13 C12 H12A 120.0 . . ? C14 C13 C12 120.0 . . ? C14 C13 H13A 120.0 . . ? C12 C13 H13A 120.0 . . ? C13 C14 C9 120.0 . . ? C13 C14 H14A 120.0 . . ? C9 C14 H14A 120.0 . . ? 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 C5 N1 C1 C2 -0.6(3) . . . . ? N1 C1 C2 C3 0.5(3) . . . . ? C1 C2 C3 C4 0.1(3) . . . . ? C2 C3 C4 C5 -0.5(3) . . . . ? C1 N1 C5 C4 0.1(2) . . . . ? C1 N1 C5 C6 -179.85(15) . . . . ? C3 C4 C5 N1 0.5(3) . . . . ? C3 C4 C5 C6 -179.60(15) . . . . ? C7 N2 C6 O1 0.4(3) . . . . ? C7 N2 C6 C5 -178.47(15) . . . . ? N1 C5 C6 O1 -178.68(15) . . . . ? C4 C5 C6 O1 1.4(2) . . . . ? N1 C5 C6 N2 0.2(2) . . . . ? C4 C5 C6 N2 -179.72(15) . . . . ? C6 N2 C7 N3 179.61(18) . . . . ? N2 C7 N3 O2 1.6(3) . . . . ? C7 N3 O2 C8 -171.00(17) . . . . ? N3 O2 C8 C9 77.7(2) . . . . ? O2 C8 C9 C14 87.83(19) . . . . ? O2 C8 C9 C10 -91.17(19) . . . . ? C14 C9 C10 C11 0.0 . . . . ? C8 C9 C10 C11 179.01(13) . . . . ? C9 C10 C11 C12 0.0 . . . . ? C10 C11 C12 C13 0.0 . . . . ? C11 C12 C13 C14 0.0 . . . . ? C12 C13 C14 C9 0.0 . . . . ? C10 C9 C14 C13 0.0 . . . . ? C8 C9 C14 C13 -178.99(14) . . . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.280 _refine_diff_density_min -0.292 _refine_diff_density_rms 0.043 data_ap16 _database_code_depnum_ccdc_archive 'CCDC 837812' #TrackingRef 'web_deposit_cif_file_0_AnnePetitjean_1312319103.ap16_July 2011.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H23 F3 N7 O7.50 S' _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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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 14.4432(8) _cell_length_b 14.6020(8) _cell_length_c 14.6895(8) _cell_angle_alpha 64.0350(10) _cell_angle_beta 76.9770(10) _cell_angle_gamma 61.12 _cell_volume 2438.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 9979 _cell_measurement_theta_min 2.21 _cell_measurement_theta_max 27.15 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.521 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1156 _exptl_absorpt_coefficient_mu 0.213 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9349 _exptl_absorpt_correction_T_max 0.9486 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 24537 _diffrn_reflns_av_R_equivalents 0.0185 _diffrn_reflns_av_sigmaI/netI 0.0214 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.54 _diffrn_reflns_theta_max 26.00 _reflns_number_total 9507 _reflns_number_gt 8004 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0625P)^2^+3.2500P] 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 9507 _refine_ls_number_parameters 703 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0663 _refine_ls_R_factor_gt 0.0569 _refine_ls_wR_factor_ref 0.1494 _refine_ls_wR_factor_gt 0.1408 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.54643(16) 0.33983(19) 0.89152(15) 0.0329(5) Uani 1 1 d . . . N2 N 0.35846(17) 0.53230(18) 0.86793(16) 0.0325(5) Uani 1 1 d . . . H2B H 0.3618 0.4681 0.8741 0.039 Uiso 1 1 calc R . . N3 N 0.17249(18) 0.63470(17) 0.84293(17) 0.0348(5) Uani 1 1 d . . . N4 N 0.17197(15) 0.35089(17) 0.83826(15) 0.0274(4) Uani 1 1 d . . . N5 N 0.45792(17) 0.06153(18) 0.86752(18) 0.0385(5) Uani 1 1 d . . . N6 N 0.54717(16) 0.15175(18) 0.88751(17) 0.0357(5) Uani 1 1 d . . . H6A H 0.4887 0.2131 0.8856 0.043 Uiso 1 1 calc R . . N7 N 0.48950(15) 0.44695(16) 0.62772(14) 0.0261(4) Uani 1 1 d . . . N8 N 0.48059(15) 0.26842(16) 0.61751(15) 0.0280(4) Uani 1 1 d . . . H8C H 0.4247 0.3337 0.6091 0.034 Uiso 1 1 calc R . . N9 N 0.39380(17) 0.18731(16) 0.57852(17) 0.0329(5) Uani 1 1 d . . . N10 N 0.13079(15) 0.49805(17) 0.50266(15) 0.0281(4) Uani 1 1 d . . . N11 N 0.12239(18) 0.75448(17) 0.56614(17) 0.0362(5) Uani 1 1 d . . . N12 N 0.30457(16) 0.63939(16) 0.60590(15) 0.0286(4) Uani 1 1 d . . . H12B H 0.3084 0.5804 0.5996 0.034 Uiso 1 1 calc R . . O1 O 0.44852(17) 0.62431(18) 0.86697(16) 0.0472(5) Uani 1 1 d . . . O2 O 0.18359(14) 0.52872(14) 0.85417(14) 0.0356(4) Uani 1 1 d . . . O3 O 0.36814(14) 0.15967(15) 0.87285(15) 0.0375(4) Uani 1 1 d . . . O4 O 0.72461(17) 0.06013(19) 0.9075(2) 0.0640(7) Uani 1 1 d . . . O5 O 0.65720(14) 0.16577(16) 0.64340(16) 0.0436(5) Uani 1 1 d . . . O6 O 0.31898(13) 0.30162(14) 0.53695(14) 0.0343(4) Uani 1 1 d . . . O7 O 0.14054(14) 0.67170(15) 0.53026(15) 0.0376(4) Uani 1 1 d . . . O8 O 0.39325(15) 0.72111(16) 0.62736(15) 0.0402(4) Uani 1 1 d . . . O1W O 0.27992(14) 0.43607(15) 0.65316(16) 0.0298(4) Uani 1 1 d . . . H1WB H 0.259(3) 0.410(3) 0.709(3) 0.046(9) Uiso 1 1 d . . . H1WA H 0.239(3) 0.449(3) 0.617(3) 0.048(10) Uiso 1 1 d . . . C1 C 0.6390(2) 0.2469(2) 0.90377(19) 0.0385(6) Uani 1 1 d . . . C2 C 0.7346(2) 0.2418(3) 0.9160(2) 0.0509(8) Uani 1 1 d . . . H2A H 0.7982 0.1740 0.9254 0.061 Uiso 1 1 calc R . . C3 C 0.7354(3) 0.3364(3) 0.9144(2) 0.0557(9) Uani 1 1 d . . . H3A H 0.7995 0.3348 0.9229 0.067 Uiso 1 1 calc R . . C4 C 0.6419(2) 0.4331(3) 0.9002(2) 0.0475(7) Uani 1 1 d . . . H4A H 0.6403 0.5001 0.8974 0.057 Uiso 1 1 calc R . . C5 C 0.5495(2) 0.4309(2) 0.88991(18) 0.0357(6) Uani 1 1 d . . . C6 C 0.4487(2) 0.5377(2) 0.87410(18) 0.0353(6) Uani 1 1 d . . . C7 C 0.2618(2) 0.6273(2) 0.8521(2) 0.0351(6) Uani 1 1 d . . . H7A H 0.2621 0.6941 0.8476 0.042 Uiso 1 1 calc R . . C8 C 0.0882(2) 0.5452(2) 0.8215(2) 0.0330(5) Uani 1 1 d . . . H8A H 0.0867 0.5757 0.7467 0.040 Uiso 1 1 calc R . . H8B H 0.0254 0.5989 0.8460 0.040 Uiso 1 1 calc R . . C9 C 0.08951(18) 0.4304(2) 0.86639(18) 0.0273(5) Uani 1 1 d . . . C10 C 0.01268(19) 0.4074(2) 0.93490(19) 0.0316(5) Uani 1 1 d . . . H10A H -0.0455 0.4657 0.9526 0.038 Uiso 1 1 calc R . . C11 C 0.0220(2) 0.2981(2) 0.97714(19) 0.0342(6) Uani 1 1 d . . . H11A H -0.0303 0.2804 1.0234 0.041 Uiso 1 1 calc R . . C12 C 0.1087(2) 0.2149(2) 0.95100(19) 0.0321(5) Uani 1 1 d . . . H12A H 0.1180 0.1388 0.9805 0.039 Uiso 1 1 calc R . . C13 C 0.18159(19) 0.2448(2) 0.88101(18) 0.0281(5) Uani 1 1 d . . . C14 C 0.2774(2) 0.1589(2) 0.8496(2) 0.0347(6) Uani 1 1 d . . . H14A H 0.2794 0.0827 0.8868 0.042 Uiso 1 1 calc R . . H14B H 0.2760 0.1786 0.7761 0.042 Uiso 1 1 calc R . . C15 C 0.5415(2) 0.0648(2) 0.8771(2) 0.0393(6) Uani 1 1 d . . . H15A H 0.6066 0.0012 0.8772 0.047 Uiso 1 1 calc R . . C16 C 0.6414(2) 0.1442(2) 0.9007(2) 0.0419(6) Uani 1 1 d . . . C17 C 0.49479(19) 0.5340(2) 0.63181(17) 0.0278(5) Uani 1 1 d . . . C18 C 0.5884(2) 0.5315(2) 0.64545(19) 0.0342(6) Uani 1 1 d . . . H18A H 0.5887 0.5956 0.6474 0.041 Uiso 1 1 calc R . . C19 C 0.6807(2) 0.4336(3) 0.6561(2) 0.0398(6) Uani 1 1 d . . . H19A H 0.7459 0.4289 0.6660 0.048 Uiso 1 1 calc R . . C20 C 0.6772(2) 0.3426(2) 0.6523(2) 0.0357(6) Uani 1 1 d . . . H20A H 0.7398 0.2744 0.6592 0.043 Uiso 1 1 calc R . . C21 C 0.58013(19) 0.3529(2) 0.63821(17) 0.0285(5) Uani 1 1 d . . . C22 C 0.57635(19) 0.2538(2) 0.63403(18) 0.0295(5) Uani 1 1 d . . . C23 C 0.4711(2) 0.1799(2) 0.61397(19) 0.0323(5) Uani 1 1 d . . . H23A H 0.5278 0.1065 0.6406 0.039 Uiso 1 1 calc R . . C24 C 0.2295(2) 0.3065(2) 0.5063(2) 0.0352(6) Uani 1 1 d . . . H24A H 0.1931 0.2703 0.5660 0.042 Uiso 1 1 calc R . . H24B H 0.2517 0.2663 0.4600 0.042 Uiso 1 1 calc R . . C25 C 0.15674(18) 0.4300(2) 0.45308(19) 0.0282(5) Uani 1 1 d . . . C26 C 0.11946(19) 0.4695(2) 0.3576(2) 0.0327(5) Uani 1 1 d . . . H26A H 0.1398 0.4194 0.3243 0.039 Uiso 1 1 calc R . . C27 C 0.0524(2) 0.5828(2) 0.3119(2) 0.0338(5) Uani 1 1 d . . . H27A H 0.0246 0.6115 0.2471 0.041 Uiso 1 1 calc R . . C28 C 0.02584(19) 0.6542(2) 0.36127(19) 0.0309(5) Uani 1 1 d . . . H28A H -0.0194 0.7328 0.3307 0.037 Uiso 1 1 calc R . . C29 C 0.06676(18) 0.6085(2) 0.45646(18) 0.0269(5) Uani 1 1 d . . . C30 C 0.04172(19) 0.6831(2) 0.5127(2) 0.0328(5) Uani 1 1 d . . . H30A H -0.0041 0.7630 0.4718 0.039 Uiso 1 1 calc R . . H30B H 0.0048 0.6586 0.5778 0.039 Uiso 1 1 calc R . . C31 C 0.2079(2) 0.7324(2) 0.59941(19) 0.0333(5) Uani 1 1 d . . . H31A H 0.2052 0.7854 0.6222 0.040 Uiso 1 1 calc R . . C32 C 0.3934(2) 0.6398(2) 0.62201(17) 0.0290(5) Uani 1 1 d . . . S1 S 0.11729(6) 0.00016(7) 0.71670(6) 0.0474(2) Uani 1 1 d . . . C33 C 0.0643(3) 0.0034(3) 0.8398(3) 0.0560(8) Uani 1 1 d . A . O11A O 0.0174(3) 0.0483(3) 0.6681(3) 0.0522(8) Uani 0.641(6) 1 d P A 1 O12A O 0.1894(4) -0.1068(3) 0.7301(3) 0.0522(8) Uani 0.641(6) 1 d P A 1 O13A O 0.1588(5) 0.0859(5) 0.6796(4) 0.0522(8) Uani 0.641(6) 1 d P A 1 F11A F -0.0038(3) 0.1046(3) 0.8428(3) 0.0661(8) Uani 0.641(6) 1 d P A 1 F12A F 0.0223(4) -0.0645(4) 0.8973(3) 0.0661(8) Uani 0.641(6) 1 d P A 1 F13A F 0.1509(3) -0.0263(4) 0.8947(3) 0.0661(8) Uani 0.641(6) 1 d P A 1 O11B O 0.0508(5) -0.0182(7) 0.6703(5) 0.0520(14) Uani 0.359(6) 1 d P A 2 O12B O 0.2150(5) -0.1247(6) 0.7640(6) 0.0520(14) Uani 0.359(6) 1 d P A 2 O13B O 0.1493(8) 0.0799(9) 0.6637(8) 0.0520(14) Uani 0.359(6) 1 d P A 2 F11B F -0.0390(6) 0.0946(6) 0.8087(6) 0.0740(16) Uani 0.359(6) 1 d P A 2 F12B F 0.0514(7) -0.0954(7) 0.8902(7) 0.0740(16) Uani 0.359(6) 1 d P A 2 F13B F 0.1084(7) 0.0213(7) 0.8856(6) 0.0740(16) Uani 0.359(6) 1 d P A 2 S2 S 0.29508(5) 0.23127(6) 0.24489(5) 0.03535(16) Uani 1 1 d . B . C34 C 0.2924(2) 0.2942(3) 0.1081(2) 0.0507(8) Uani 1 1 d . . . O21 O 0.18461(16) 0.27254(19) 0.27277(18) 0.0509(5) Uani 1 1 d . . . O22 O 0.35143(16) 0.2771(2) 0.26819(17) 0.0513(5) Uani 1 1 d . . . O23 O 0.34961(18) 0.11228(17) 0.26810(18) 0.0563(6) Uani 1 1 d . . . F21A F 0.3941(5) 0.2440(7) 0.0690(5) 0.0546(14) Uani 0.471(18) 1 d P B 1 F22A F 0.2217(7) 0.2889(8) 0.0708(4) 0.0546(14) Uani 0.471(18) 1 d P B 1 F23A F 0.2397(5) 0.4173(6) 0.0894(6) 0.0546(14) Uani 0.471(18) 1 d P B 1 F21B F 0.3835(5) 0.2827(7) 0.0648(4) 0.0621(13) Uani 0.529(18) 1 d P B 2 F22B F 0.2527(7) 0.2458(8) 0.0739(4) 0.0621(13) Uani 0.529(18) 1 d P B 2 F23B F 0.2534(5) 0.3983(6) 0.0632(5) 0.0621(13) Uani 0.529(18) 1 d P B 2 N13A N 0.1418(3) 0.0085(3) 0.3413(3) 0.0597(10) Uani 0.724(5) 1 d P C 1 H13A H 0.0987 -0.0264 0.3555 0.072 Uiso 0.724(5) 1 calc PR C 1 H13B H 0.2100 -0.0444 0.3378 0.072 Uiso 0.724(5) 1 calc PR C 1 C35A C 0.1352(3) 0.0346(3) 0.4251(3) 0.0623(9) Uani 0.724(5) 1 d P C 1 H35A H 0.1520 -0.0343 0.4869 0.093 Uiso 0.724(5) 1 calc PR C 1 H35B H 0.0633 0.0911 0.4310 0.093 Uiso 0.724(5) 1 calc PR C 1 H35C H 0.1856 0.0651 0.4155 0.093 Uiso 0.724(5) 1 calc PR C 1 C36A C 0.116(2) 0.096(2) 0.243(2) 0.101(3) Uani 0.724(5) 1 d P C 1 H36A H 0.1240 0.0637 0.1938 0.152 Uiso 0.724(5) 1 calc PR C 1 H36B H 0.1634 0.1324 0.2232 0.152 Uiso 0.724(5) 1 calc PR C 1 H36C H 0.0426 0.1529 0.2429 0.152 Uiso 0.724(5) 1 calc PR C 1 N13B N 0.0980(7) 0.1091(9) 0.3234(9) 0.0597(10) Uani 0.276(5) 1 d P C 2 H13C H 0.0260 0.1329 0.3272 0.072 Uiso 0.276(5) 1 calc PR C 2 H13D H 0.1078 0.1720 0.3086 0.072 Uiso 0.276(5) 1 calc PR C 2 C35B C 0.1352(3) 0.0346(3) 0.4251(3) 0.0623(9) Uani 0.276(5) 1 d P C 2 H35D H 0.1084 0.0784 0.4680 0.093 Uiso 0.276(5) 1 calc PR C 2 H35E H 0.2127 -0.0015 0.4244 0.093 Uiso 0.276(5) 1 calc PR C 2 H35F H 0.1098 -0.0239 0.4519 0.093 Uiso 0.276(5) 1 calc PR C 2 C36B C 0.130(6) 0.085(6) 0.244(6) 0.101(3) Uani 0.276(5) 1 d P C 2 H36D H 0.0975 0.1528 0.1838 0.152 Uiso 0.276(5) 1 calc PR C 2 H36E H 0.1104 0.0266 0.2504 0.152 Uiso 0.276(5) 1 calc PR C 2 H36F H 0.2073 0.0557 0.2374 0.152 Uiso 0.276(5) 1 calc PR C 2 N14 N 0.42326(19) 0.85030(19) 0.71153(18) 0.0383(5) Uani 1 1 d . . . H14C H 0.4884 0.7885 0.7246 0.046 Uiso 1 1 calc R . . H14D H 0.3738 0.8251 0.7181 0.046 Uiso 1 1 calc R . . C37 C 0.4234(3) 0.9305(3) 0.6067(2) 0.0539(8) Uani 1 1 d . . . H37A H 0.4394 0.8928 0.5601 0.081 Uiso 1 1 calc R . . H37B H 0.4772 0.9562 0.5986 0.081 Uiso 1 1 calc R . . H37C H 0.3537 0.9958 0.5915 0.081 Uiso 1 1 calc R . . C38 C 0.3996(2) 0.9000(3) 0.7874(3) 0.0500(8) Uani 1 1 d . . . H38A H 0.4015 0.8425 0.8554 0.075 Uiso 1 1 calc R . . H38B H 0.3291 0.9642 0.7755 0.075 Uiso 1 1 calc R . . H38C H 0.4524 0.9262 0.7815 0.075 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0321(11) 0.0424(12) 0.0242(10) -0.0082(9) -0.0003(8) -0.0206(10) N2 0.0375(12) 0.0324(11) 0.0340(11) -0.0134(9) 0.0024(9) -0.0208(10) N3 0.0415(12) 0.0270(11) 0.0393(12) -0.0159(9) 0.0045(9) -0.0170(10) N4 0.0268(10) 0.0303(10) 0.0269(10) -0.0125(8) 0.0002(8) -0.0128(8) N5 0.0329(12) 0.0293(11) 0.0456(13) -0.0185(10) 0.0035(10) -0.0060(9) N6 0.0264(10) 0.0326(11) 0.0394(12) -0.0123(9) 0.0011(9) -0.0086(9) N7 0.0281(10) 0.0286(10) 0.0220(9) -0.0090(8) 0.0006(7) -0.0140(8) N8 0.0260(10) 0.0212(9) 0.0326(11) -0.0107(8) -0.0024(8) -0.0061(8) N9 0.0337(11) 0.0199(10) 0.0411(12) -0.0118(9) -0.0035(9) -0.0075(9) N10 0.0265(10) 0.0284(10) 0.0320(10) -0.0126(8) -0.0004(8) -0.0131(8) N11 0.0405(12) 0.0253(10) 0.0459(13) -0.0205(10) -0.0094(10) -0.0072(9) N12 0.0340(11) 0.0242(10) 0.0321(11) -0.0134(8) -0.0031(8) -0.0129(9) O1 0.0591(13) 0.0527(12) 0.0506(12) -0.0235(10) 0.0074(10) -0.0401(11) O2 0.0341(9) 0.0259(9) 0.0491(11) -0.0138(8) -0.0063(8) -0.0130(7) O3 0.0277(9) 0.0323(9) 0.0557(12) -0.0264(9) 0.0026(8) -0.0086(8) O4 0.0316(11) 0.0463(13) 0.0920(19) -0.0177(12) -0.0136(11) -0.0036(10) O5 0.0280(9) 0.0325(10) 0.0615(13) -0.0205(9) -0.0039(9) -0.0035(8) O6 0.0311(9) 0.0209(8) 0.0507(11) -0.0133(8) -0.0096(8) -0.0082(7) O7 0.0311(9) 0.0326(9) 0.0581(12) -0.0294(9) -0.0076(8) -0.0072(8) O8 0.0476(11) 0.0366(10) 0.0511(11) -0.0236(9) -0.0005(9) -0.0235(9) O1W 0.0310(9) 0.0309(9) 0.0282(10) -0.0116(8) 0.0016(8) -0.0148(8) C1 0.0311(13) 0.0468(16) 0.0289(13) -0.0058(11) -0.0032(10) -0.0173(12) C2 0.0322(15) 0.066(2) 0.0467(17) -0.0141(15) -0.0066(12) -0.0200(14) C3 0.0406(17) 0.089(3) 0.0514(18) -0.0258(18) -0.0033(14) -0.0382(18) C4 0.0487(17) 0.073(2) 0.0380(15) -0.0222(15) 0.0028(13) -0.0400(17) C5 0.0383(14) 0.0520(16) 0.0241(12) -0.0125(11) 0.0028(10) -0.0285(13) C6 0.0449(15) 0.0474(15) 0.0249(12) -0.0140(11) 0.0059(10) -0.0313(13) C7 0.0433(15) 0.0316(13) 0.0371(14) -0.0168(11) 0.0067(11) -0.0214(12) C8 0.0304(13) 0.0299(13) 0.0367(13) -0.0124(11) -0.0045(10) -0.0106(10) C9 0.0252(11) 0.0293(12) 0.0288(12) -0.0125(10) -0.0051(9) -0.0099(10) C10 0.0249(12) 0.0366(13) 0.0361(13) -0.0199(11) 0.0001(10) -0.0105(10) C11 0.0305(13) 0.0457(15) 0.0333(13) -0.0177(11) 0.0055(10) -0.0221(12) C12 0.0337(13) 0.0323(13) 0.0339(13) -0.0116(10) -0.0010(10) -0.0180(11) C13 0.0290(12) 0.0301(12) 0.0293(12) -0.0136(10) -0.0015(9) -0.0136(10) C14 0.0341(13) 0.0348(13) 0.0420(14) -0.0205(11) 0.0033(11) -0.0168(11) C15 0.0313(13) 0.0305(13) 0.0439(15) -0.0137(12) 0.0006(11) -0.0056(11) C16 0.0301(14) 0.0392(15) 0.0394(15) -0.0046(12) -0.0048(11) -0.0102(12) C17 0.0336(12) 0.0313(12) 0.0214(11) -0.0092(9) 0.0026(9) -0.0185(10) C18 0.0395(14) 0.0422(14) 0.0311(13) -0.0148(11) 0.0070(10) -0.0280(12) C19 0.0306(13) 0.0556(17) 0.0405(15) -0.0180(13) 0.0063(11) -0.0278(13) C20 0.0260(12) 0.0426(15) 0.0351(13) -0.0135(11) 0.0044(10) -0.0159(11) C21 0.0289(12) 0.0314(12) 0.0219(11) -0.0085(9) 0.0021(9) -0.0136(10) C22 0.0270(12) 0.0282(12) 0.0274(12) -0.0088(10) -0.0003(9) -0.0095(10) C23 0.0332(13) 0.0220(11) 0.0363(13) -0.0117(10) -0.0017(10) -0.0073(10) C24 0.0337(13) 0.0281(13) 0.0489(15) -0.0160(11) -0.0044(11) -0.0148(11) C25 0.0240(11) 0.0291(12) 0.0368(13) -0.0149(10) 0.0016(9) -0.0144(10) C26 0.0310(12) 0.0389(14) 0.0399(14) -0.0227(11) 0.0010(10) -0.0179(11) C27 0.0327(13) 0.0408(14) 0.0328(13) -0.0151(11) -0.0048(10) -0.0171(11) C28 0.0267(12) 0.0299(12) 0.0348(13) -0.0111(10) -0.0041(10) -0.0111(10) C29 0.0224(11) 0.0275(12) 0.0321(12) -0.0128(10) 0.0002(9) -0.0110(9) C30 0.0286(12) 0.0314(13) 0.0386(14) -0.0180(11) -0.0046(10) -0.0077(10) C31 0.0409(14) 0.0234(12) 0.0368(13) -0.0135(10) -0.0082(11) -0.0102(11) C32 0.0382(13) 0.0306(12) 0.0235(11) -0.0106(10) 0.0006(9) -0.0193(11) S1 0.0451(4) 0.0561(5) 0.0440(4) -0.0145(3) -0.0026(3) -0.0279(4) C33 0.063(2) 0.0484(19) 0.057(2) -0.0145(16) 0.0081(16) -0.0333(17) O11A 0.0632(16) 0.0326(13) 0.0549(14) -0.0054(10) -0.0126(11) -0.0220(11) O12A 0.0632(16) 0.0326(13) 0.0549(14) -0.0054(10) -0.0126(11) -0.0220(11) O13A 0.0632(16) 0.0326(13) 0.0549(14) -0.0054(10) -0.0126(11) -0.0220(11) F11A 0.0738(16) 0.0684(15) 0.0561(12) -0.0267(11) 0.0105(11) -0.0338(12) F12A 0.0738(16) 0.0684(15) 0.0561(12) -0.0267(11) 0.0105(11) -0.0338(12) F13A 0.0738(16) 0.0684(15) 0.0561(12) -0.0267(11) 0.0105(11) -0.0338(12) O11B 0.028(2) 0.052(3) 0.067(3) -0.021(2) 0.0012(18) -0.0142(18) O12B 0.028(2) 0.052(3) 0.067(3) -0.021(2) 0.0012(18) -0.0142(18) O13B 0.028(2) 0.052(3) 0.067(3) -0.021(2) 0.0012(18) -0.0142(18) F11B 0.084(3) 0.079(3) 0.091(3) -0.057(3) 0.038(2) -0.054(3) F12B 0.084(3) 0.079(3) 0.091(3) -0.057(3) 0.038(2) -0.054(3) F13B 0.084(3) 0.079(3) 0.091(3) -0.057(3) 0.038(2) -0.054(3) S2 0.0334(3) 0.0354(3) 0.0396(4) -0.0196(3) 0.0032(3) -0.0139(3) C34 0.0437(17) 0.062(2) 0.0452(17) -0.0101(15) -0.0059(13) -0.0294(16) O21 0.0383(11) 0.0583(13) 0.0745(15) -0.0442(12) 0.0156(10) -0.0253(10) O22 0.0428(11) 0.0651(14) 0.0627(14) -0.0372(12) 0.0013(10) -0.0257(11) O23 0.0583(14) 0.0344(11) 0.0628(14) -0.0172(10) 0.0007(11) -0.0127(10) F21A 0.055(2) 0.057(2) 0.0515(17) -0.0223(15) -0.0048(13) -0.0217(17) F22A 0.055(2) 0.057(2) 0.0515(17) -0.0223(15) -0.0048(13) -0.0217(17) F23A 0.055(2) 0.057(2) 0.0515(17) -0.0223(15) -0.0048(13) -0.0217(17) F21B 0.0676(19) 0.063(3) 0.0468(16) -0.0191(15) 0.0022(12) -0.0256(18) F22B 0.0676(19) 0.063(3) 0.0468(16) -0.0191(15) 0.0022(12) -0.0256(18) F23B 0.0676(19) 0.063(3) 0.0468(16) -0.0191(15) 0.0022(12) -0.0256(18) N13A 0.0330(17) 0.051(2) 0.090(3) -0.041(2) -0.0098(17) 0.0007(15) C35A 0.061(2) 0.059(2) 0.053(2) -0.0192(17) 0.0029(16) -0.0199(18) C36A 0.167(9) 0.143(8) 0.057(3) -0.020(5) -0.003(5) -0.131(7) N13B 0.0330(17) 0.051(2) 0.090(3) -0.041(2) -0.0098(17) 0.0007(15) C35B 0.061(2) 0.059(2) 0.053(2) -0.0192(17) 0.0029(16) -0.0199(18) C36B 0.167(9) 0.143(8) 0.057(3) -0.020(5) -0.003(5) -0.131(7) N14 0.0423(13) 0.0331(12) 0.0481(13) -0.0213(10) 0.0020(10) -0.0190(10) C37 0.075(2) 0.0420(17) 0.0513(18) -0.0170(14) 0.0056(16) -0.0340(16) C38 0.0396(16) 0.0595(19) 0.063(2) -0.0418(17) 0.0003(14) -0.0148(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C5 1.341(3) . ? N1 C1 1.343(3) . ? N2 C6 1.368(3) . ? N2 C7 1.386(3) . ? N2 H2B 0.8800 . ? N3 C7 1.274(3) . ? N3 O2 1.413(3) . ? N4 C13 1.338(3) . ? N4 C9 1.342(3) . ? N5 C15 1.272(4) . ? N5 O3 1.414(3) . ? N6 C16 1.363(4) . ? N6 C15 1.385(4) . ? N6 H6A 0.8800 . ? N7 C17 1.337(3) . ? N7 C21 1.339(3) . ? N8 C22 1.356(3) . ? N8 C23 1.388(3) . ? N8 H8C 0.8800 . ? N9 C23 1.274(3) . ? N9 O6 1.411(3) . ? N10 C29 1.342(3) . ? N10 C25 1.346(3) . ? N11 C31 1.272(3) . ? N11 O7 1.413(2) . ? N12 C32 1.359(3) . ? N12 C31 1.385(3) . ? N12 H12B 0.8800 . ? O1 C6 1.221(3) . ? O2 C8 1.436(3) . ? O3 C14 1.434(3) . ? O4 C16 1.217(3) . ? O5 C22 1.226(3) . ? O6 C24 1.422(3) . ? O7 C30 1.424(3) . ? O8 C32 1.223(3) . ? O1W H1WB 0.80(4) . ? O1W H1WA 0.79(4) . ? C1 C2 1.394(4) . ? C1 C16 1.504(4) . ? C2 C3 1.377(5) . ? C2 H2A 0.9500 . ? C3 C4 1.375(5) . ? C3 H3A 0.9500 . ? C4 C5 1.394(4) . ? C4 H4A 0.9500 . ? C5 C6 1.499(4) . ? C7 H7A 0.9500 . ? C8 C9 1.501(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.385(3) . ? C10 C11 1.384(4) . ? C10 H10A 0.9500 . ? C11 C12 1.383(4) . ? C11 H11A 0.9500 . ? C12 C13 1.386(3) . ? C12 H12A 0.9500 . ? C13 C14 1.499(3) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9500 . ? C17 C18 1.393(3) . ? C17 C32 1.506(3) . ? C18 C19 1.379(4) . ? C18 H18A 0.9500 . ? C19 C20 1.380(4) . ? C19 H19A 0.9500 . ? C20 C21 1.390(3) . ? C20 H20A 0.9500 . ? C21 C22 1.502(3) . ? C23 H23A 0.9500 . ? C24 C25 1.507(3) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 C26 1.386(4) . ? C26 C27 1.378(4) . ? C26 H26A 0.9500 . ? C27 C28 1.383(4) . ? C27 H27A 0.9500 . ? C28 C29 1.387(3) . ? C28 H28A 0.9500 . ? C29 C30 1.509(3) . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C31 H31A 0.9500 . ? S1 O13B 1.318(11) . ? S1 O12A 1.347(4) . ? S1 O11A 1.459(4) . ? S1 O11B 1.470(7) . ? S1 O13A 1.484(5) . ? S1 O12B 1.627(7) . ? S1 C33 1.810(4) . ? C33 F13B 1.199(9) . ? C33 F12A 1.296(6) . ? C33 F11A 1.337(5) . ? C33 F12B 1.386(9) . ? C33 F13A 1.424(6) . ? C33 F11B 1.436(9) . ? S2 O23 1.427(2) . ? S2 O21 1.439(2) . ? S2 O22 1.442(2) . ? S2 C34 1.808(3) . ? C34 F23B 1.235(7) . ? C34 F21B 1.291(7) . ? C34 F22A 1.309(7) . ? C34 F22B 1.383(7) . ? C34 F21A 1.405(8) . ? C34 F23A 1.491(8) . ? N13A C35A 1.410(5) . ? N13A C36A 1.43(3) . ? N13A H13A 0.9200 . ? N13A H13B 0.9200 . ? C35A H35A 0.9800 . ? C35A H35B 0.9800 . ? C35A H35C 0.9800 . ? C36A H36A 0.9800 . ? C36A H36B 0.9800 . ? C36A H36C 0.9800 . ? N13B C36B 1.29(8) . ? N13B H13C 0.9200 . ? N13B H13D 0.9200 . ? C36B H36D 0.9800 . ? C36B H36E 0.9800 . ? C36B H36F 0.9800 . ? N14 C37 1.471(4) . ? N14 C38 1.476(3) . ? N14 H14C 0.9200 . ? N14 H14D 0.9200 . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 0.9800 . ? C38 H38A 0.9800 . ? C38 H38B 0.9800 . ? C38 H38C 0.9800 . ? 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 C5 N1 C1 116.6(2) . . ? C6 N2 C7 120.5(2) . . ? C6 N2 H2B 119.8 . . ? C7 N2 H2B 119.8 . . ? C7 N3 O2 110.2(2) . . ? C13 N4 C9 118.3(2) . . ? C15 N5 O3 109.8(2) . . ? C16 N6 C15 121.3(2) . . ? C16 N6 H6A 119.3 . . ? C15 N6 H6A 119.3 . . ? C17 N7 C21 117.0(2) . . ? C22 N8 C23 119.7(2) . . ? C22 N8 H8C 120.1 . . ? C23 N8 H8C 120.1 . . ? C23 N9 O6 110.17(19) . . ? C29 N10 C25 117.9(2) . . ? C31 N11 O7 109.8(2) . . ? C32 N12 C31 119.6(2) . . ? C32 N12 H12B 120.2 . . ? C31 N12 H12B 120.2 . . ? N3 O2 C8 108.65(18) . . ? N5 O3 C14 107.75(18) . . ? N9 O6 C24 108.94(17) . . ? N11 O7 C30 109.32(17) . . ? H1WB O1W H1WA 105(3) . . ? N1 C1 C2 123.2(3) . . ? N1 C1 C16 119.0(2) . . ? C2 C1 C16 117.8(3) . . ? C3 C2 C1 119.1(3) . . ? C3 C2 H2A 120.5 . . ? C1 C2 H2A 120.5 . . ? C4 C3 C2 118.8(3) . . ? C4 C3 H3A 120.6 . . ? C2 C3 H3A 120.6 . . ? C3 C4 C5 118.6(3) . . ? C3 C4 H4A 120.7 . . ? C5 C4 H4A 120.7 . . ? N1 C5 C4 123.8(3) . . ? N1 C5 C6 118.7(2) . . ? C4 C5 C6 117.5(3) . . ? O1 C6 N2 122.5(3) . . ? O1 C6 C5 121.0(2) . . ? N2 C6 C5 116.4(2) . . ? N3 C7 N2 127.0(2) . . ? N3 C7 H7A 116.5 . . ? N2 C7 H7A 116.5 . . ? O2 C8 C9 105.78(19) . . ? O2 C8 H8A 110.6 . . ? C9 C8 H8A 110.6 . . ? O2 C8 H8B 110.6 . . ? C9 C8 H8B 110.6 . . ? H8A C8 H8B 108.7 . . ? N4 C9 C10 122.4(2) . . ? N4 C9 C8 115.5(2) . . ? C10 C9 C8 122.1(2) . . ? C11 C10 C9 118.9(2) . . ? C11 C10 H10A 120.5 . . ? C9 C10 H10A 120.5 . . ? C12 C11 C10 118.9(2) . . ? C12 C11 H11A 120.5 . . ? C10 C11 H11A 120.5 . . ? C11 C12 C13 118.8(2) . . ? C11 C12 H12A 120.6 . . ? C13 C12 H12A 120.6 . . ? N4 C13 C12 122.6(2) . . ? N4 C13 C14 115.9(2) . . ? C12 C13 C14 121.5(2) . . ? O3 C14 C13 107.15(19) . . ? O3 C14 H14A 110.3 . . ? C13 C14 H14A 110.3 . . ? O3 C14 H14B 110.3 . . ? C13 C14 H14B 110.3 . . ? H14A C14 H14B 108.5 . . ? N5 C15 N6 126.6(2) . . ? N5 C15 H15A 116.7 . . ? N6 C15 H15A 116.7 . . ? O4 C16 N6 122.6(3) . . ? O4 C16 C1 120.7(3) . . ? N6 C16 C1 116.7(2) . . ? N7 C17 C18 123.6(2) . . ? N7 C17 C32 117.8(2) . . ? C18 C17 C32 118.6(2) . . ? C19 C18 C17 118.3(2) . . ? C19 C18 H18A 120.9 . . ? C17 C18 H18A 120.9 . . ? C18 C19 C20 119.2(2) . . ? C18 C19 H19A 120.4 . . ? C20 C19 H19A 120.4 . . ? C19 C20 C21 118.6(2) . . ? C19 C20 H20A 120.7 . . ? C21 C20 H20A 120.7 . . ? N7 C21 C20 123.4(2) . . ? N7 C21 C22 118.1(2) . . ? C20 C21 C22 118.5(2) . . ? O5 C22 N8 122.8(2) . . ? O5 C22 C21 120.5(2) . . ? N8 C22 C21 116.6(2) . . ? N9 C23 N8 126.5(2) . . ? N9 C23 H23A 116.8 . . ? N8 C23 H23A 116.8 . . ? O6 C24 C25 107.18(19) . . ? O6 C24 H24A 110.3 . . ? C25 C24 H24A 110.3 . . ? O6 C24 H24B 110.3 . . ? C25 C24 H24B 110.3 . . ? H24A C24 H24B 108.5 . . ? N10 C25 C26 122.6(2) . . ? N10 C25 C24 116.8(2) . . ? C26 C25 C24 120.6(2) . . ? C27 C26 C25 118.9(2) . . ? C27 C26 H26A 120.6 . . ? C25 C26 H26A 120.6 . . ? C26 C27 C28 119.3(2) . . ? C26 C27 H27A 120.4 . . ? C28 C27 H27A 120.4 . . ? C27 C28 C29 118.5(2) . . ? C27 C28 H28A 120.7 . . ? C29 C28 H28A 120.7 . . ? N10 C29 C28 122.9(2) . . ? N10 C29 C30 116.6(2) . . ? C28 C29 C30 120.6(2) . . ? O7 C30 C29 106.28(19) . . ? O7 C30 H30A 110.5 . . ? C29 C30 H30A 110.5 . . ? O7 C30 H30B 110.5 . . ? C29 C30 H30B 110.5 . . ? H30A C30 H30B 108.7 . . ? N11 C31 N12 126.9(2) . . ? N11 C31 H31A 116.6 . . ? N12 C31 H31A 116.6 . . ? O8 C32 N12 123.0(2) . . ? O8 C32 C17 120.6(2) . . ? N12 C32 C17 116.4(2) . . ? O13B S1 O12A 116.1(5) . . ? O13B S1 O11A 101.1(4) . . ? O12A S1 O11A 119.9(2) . . ? O13B S1 O11B 120.5(5) . . ? O12A S1 O11B 86.7(3) . . ? O11A S1 O11B 33.3(3) . . ? O13B S1 O13A 12.8(5) . . ? O12A S1 O13A 116.2(3) . . ? O11A S1 O13A 110.0(3) . . ? O11B S1 O13A 132.7(3) . . ? O13B S1 O12B 112.6(5) . . ? O12A S1 O12B 19.5(3) . . ? O11A S1 O12B 136.9(3) . . ? O11B S1 O12B 104.1(4) . . ? O13A S1 O12B 108.2(4) . . ? O13B S1 C33 112.1(5) . . ? O12A S1 C33 108.1(2) . . ? O11A S1 C33 98.0(2) . . ? O11B S1 C33 110.5(3) . . ? O13A S1 C33 101.1(3) . . ? O12B S1 C33 93.4(3) . . ? F13B C33 F12A 113.8(5) . . ? F13B C33 F11A 74.8(4) . . ? F12A C33 F11A 105.4(3) . . ? F13B C33 F12B 115.9(6) . . ? F12A C33 F12B 20.2(3) . . ? F11A C33 F12B 125.6(4) . . ? F13B C33 F13A 26.9(4) . . ? F12A C33 F13A 105.8(4) . . ? F11A C33 F13A 101.7(4) . . ? F12B C33 F13A 99.3(5) . . ? F13B C33 F11B 111.8(5) . . ? F12A C33 F11B 90.3(4) . . ? F11A C33 F11B 37.0(3) . . ? F12B C33 F11B 106.7(5) . . ? F13A C33 F11B 138.7(4) . . ? F13B C33 S1 118.1(4) . . ? F12A C33 S1 119.0(3) . . ? F11A C33 S1 116.9(3) . . ? F12B C33 S1 104.1(4) . . ? F13A C33 S1 106.1(3) . . ? F11B C33 S1 98.1(4) . . ? O23 S2 O21 115.00(14) . . ? O23 S2 O22 115.03(14) . . ? O21 S2 O22 114.85(12) . . ? O23 S2 C34 104.01(16) . . ? O21 S2 C34 102.72(15) . . ? O22 S2 C34 102.81(14) . . ? F23B C34 F21B 92.0(6) . . ? F23B C34 F22A 91.1(4) . . ? F21B C34 F22A 122.3(5) . . ? F23B C34 F22B 111.7(4) . . ? F21B C34 F22B 108.0(4) . . ? F22A C34 F22B 23.7(3) . . ? F23B C34 F21A 110.3(6) . . ? F21B C34 F21A 20.2(3) . . ? F22A C34 F21A 111.5(4) . . ? F22B C34 F21A 92.5(4) . . ? F23B C34 F23A 19.2(3) . . ? F21B C34 F23A 101.3(6) . . ? F22A C34 F23A 99.8(5) . . ? F22B C34 F23A 123.0(4) . . ? F21A C34 F23A 121.3(6) . . ? F23B C34 S2 120.2(5) . . ? F21B C34 S2 114.3(3) . . ? F22A C34 S2 113.2(3) . . ? F22B C34 S2 109.2(3) . . ? F21A C34 S2 109.4(3) . . ? F23A C34 S2 101.1(4) . . ? C35A N13A C36A 120.2(12) . . ? C35A N13A H13A 107.3 . . ? C36A N13A H13A 107.3 . . ? C35A N13A H13B 107.3 . . ? C36A N13A H13B 107.3 . . ? H13A N13A H13B 106.9 . . ? N13A C35A H35A 109.5 . . ? N13A C35A H35B 109.5 . . ? H35A C35A H35B 109.5 . . ? N13A C35A H35C 109.5 . . ? H35A C35A H35C 109.5 . . ? H35B C35A H35C 109.5 . . ? N13A C36A H36A 109.5 . . ? N13A C36A H36B 109.5 . . ? H36A C36A H36B 109.5 . . ? N13A C36A H36C 109.5 . . ? H36A C36A H36C 109.5 . . ? H36B C36A H36C 109.5 . . ? C36B N13B H13C 105.7 . . ? C36B N13B H13D 105.7 . . ? H13C N13B H13D 106.2 . . ? N13B C36B H36D 109.5 . . ? N13B C36B H36E 109.5 . . ? H36D C36B H36E 109.5 . . ? N13B C36B H36F 109.5 . . ? H36D C36B H36F 109.5 . . ? H36E C36B H36F 109.5 . . ? C37 N14 C38 113.3(2) . . ? C37 N14 H14C 108.9 . . ? C38 N14 H14C 108.9 . . ? C37 N14 H14D 108.9 . . ? C38 N14 H14D 108.9 . . ? H14C N14 H14D 107.7 . . ? N14 C37 H37A 109.5 . . ? N14 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? N14 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? N14 C38 H38A 109.5 . . ? N14 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? N14 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C7 N3 O2 C8 -167.3(2) . . . . ? C15 N5 O3 C14 173.2(2) . . . . ? C23 N9 O6 C24 -174.8(2) . . . . ? C31 N11 O7 C30 168.2(2) . . . . ? C5 N1 C1 C2 1.0(4) . . . . ? C5 N1 C1 C16 -176.8(2) . . . . ? N1 C1 C2 C3 -0.9(4) . . . . ? C16 C1 C2 C3 177.0(3) . . . . ? C1 C2 C3 C4 -0.3(5) . . . . ? C2 C3 C4 C5 1.2(4) . . . . ? C1 N1 C5 C4 -0.1(4) . . . . ? C1 N1 C5 C6 178.6(2) . . . . ? C3 C4 C5 N1 -1.0(4) . . . . ? C3 C4 C5 C6 -179.8(3) . . . . ? C7 N2 C6 O1 0.6(4) . . . . ? C7 N2 C6 C5 -179.2(2) . . . . ? N1 C5 C6 O1 -176.3(2) . . . . ? C4 C5 C6 O1 2.5(4) . . . . ? N1 C5 C6 N2 3.5(3) . . . . ? C4 C5 C6 N2 -177.7(2) . . . . ? O2 N3 C7 N2 1.7(4) . . . . ? C6 N2 C7 N3 178.5(2) . . . . ? N3 O2 C8 C9 -161.58(19) . . . . ? C13 N4 C9 C10 -2.4(3) . . . . ? C13 N4 C9 C8 175.5(2) . . . . ? O2 C8 C9 N4 -60.0(3) . . . . ? O2 C8 C9 C10 117.8(2) . . . . ? N4 C9 C10 C11 1.0(4) . . . . ? C8 C9 C10 C11 -176.7(2) . . . . ? C9 C10 C11 C12 1.2(4) . . . . ? C10 C11 C12 C13 -1.9(4) . . . . ? C9 N4 C13 C12 1.6(3) . . . . ? C9 N4 C13 C14 -177.7(2) . . . . ? C11 C12 C13 N4 0.6(4) . . . . ? C11 C12 C13 C14 179.8(2) . . . . ? N5 O3 C14 C13 165.7(2) . . . . ? N4 C13 C14 O3 57.7(3) . . . . ? C12 C13 C14 O3 -121.6(2) . . . . ? O3 N5 C15 N6 -2.3(4) . . . . ? C16 N6 C15 N5 177.8(3) . . . . ? C15 N6 C16 O4 -2.6(4) . . . . ? C15 N6 C16 C1 175.8(2) . . . . ? N1 C1 C16 O4 177.1(3) . . . . ? C2 C1 C16 O4 -0.9(4) . . . . ? N1 C1 C16 N6 -1.3(4) . . . . ? C2 C1 C16 N6 -179.3(3) . . . . ? C21 N7 C17 C18 0.5(3) . . . . ? C21 N7 C17 C32 -178.94(19) . . . . ? N7 C17 C18 C19 -0.5(4) . . . . ? C32 C17 C18 C19 178.9(2) . . . . ? C17 C18 C19 C20 0.4(4) . . . . ? C18 C19 C20 C21 -0.3(4) . . . . ? C17 N7 C21 C20 -0.3(3) . . . . ? C17 N7 C21 C22 179.9(2) . . . . ? C19 C20 C21 N7 0.2(4) . . . . ? C19 C20 C21 C22 180.0(2) . . . . ? C23 N8 C22 O5 2.1(4) . . . . ? C23 N8 C22 C21 -179.2(2) . . . . ? N7 C21 C22 O5 -179.9(2) . . . . ? C20 C21 C22 O5 0.4(4) . . . . ? N7 C21 C22 N8 1.4(3) . . . . ? C20 C21 C22 N8 -178.3(2) . . . . ? O6 N9 C23 N8 3.2(4) . . . . ? C22 N8 C23 N9 -164.0(2) . . . . ? N9 O6 C24 C25 -174.44(19) . . . . ? C29 N10 C25 C26 -0.4(3) . . . . ? C29 N10 C25 C24 179.5(2) . . . . ? O6 C24 C25 N10 -51.9(3) . . . . ? O6 C24 C25 C26 128.0(2) . . . . ? N10 C25 C26 C27 -0.6(4) . . . . ? C24 C25 C26 C27 179.5(2) . . . . ? C25 C26 C27 C28 1.3(4) . . . . ? C26 C27 C28 C29 -1.0(4) . . . . ? C25 N10 C29 C28 0.8(3) . . . . ? C25 N10 C29 C30 -178.3(2) . . . . ? C27 C28 C29 N10 -0.1(4) . . . . ? C27 C28 C29 C30 179.0(2) . . . . ? N11 O7 C30 C29 169.4(2) . . . . ? N10 C29 C30 O7 58.5(3) . . . . ? C28 C29 C30 O7 -120.6(2) . . . . ? O7 N11 C31 N12 -3.2(4) . . . . ? C32 N12 C31 N11 165.6(3) . . . . ? C31 N12 C32 O8 -2.9(4) . . . . ? C31 N12 C32 C17 177.9(2) . . . . ? N7 C17 C32 O8 178.4(2) . . . . ? C18 C17 C32 O8 -1.0(3) . . . . ? N7 C17 C32 N12 -2.4(3) . . . . ? C18 C17 C32 N12 178.2(2) . . . . ? O13B S1 C33 F13B -40.3(7) . . . . ? O12A S1 C33 F13B 89.0(6) . . . . ? O11A S1 C33 F13B -145.8(5) . . . . ? O11B S1 C33 F13B -177.7(6) . . . . ? O13A S1 C33 F13B -33.4(6) . . . . ? O12B S1 C33 F13B 75.8(6) . . . . ? O13B S1 C33 F12A 174.8(5) . . . . ? O12A S1 C33 F12A -56.0(4) . . . . ? O11A S1 C33 F12A 69.2(4) . . . . ? O11B S1 C33 F12A 37.3(5) . . . . ? O13A S1 C33 F12A -178.4(4) . . . . ? O12B S1 C33 F12A -69.1(4) . . . . ? O13B S1 C33 F11A 46.2(6) . . . . ? O12A S1 C33 F11A 175.5(3) . . . . ? O11A S1 C33 F11A -59.3(4) . . . . ? O11B S1 C33 F11A -91.2(4) . . . . ? O13A S1 C33 F11A 53.1(4) . . . . ? O12B S1 C33 F11A 162.3(4) . . . . ? O13B S1 C33 F12B -170.5(7) . . . . ? O12A S1 C33 F12B -41.2(5) . . . . ? O11A S1 C33 F12B 84.0(5) . . . . ? O11B S1 C33 F12B 52.1(6) . . . . ? O13A S1 C33 F12B -163.7(5) . . . . ? O12B S1 C33 F12B -54.4(6) . . . . ? O13B S1 C33 F13A -66.3(5) . . . . ? O12A S1 C33 F13A 63.0(3) . . . . ? O11A S1 C33 F13A -171.8(3) . . . . ? O11B S1 C33 F13A 156.2(4) . . . . ? O13A S1 C33 F13A -59.5(4) . . . . ? O12B S1 C33 F13A 49.8(4) . . . . ? O13B S1 C33 F11B 79.9(6) . . . . ? O12A S1 C33 F11B -150.8(3) . . . . ? O11A S1 C33 F11B -25.6(3) . . . . ? O11B S1 C33 F11B -57.5(4) . . . . ? O13A S1 C33 F11B 86.7(4) . . . . ? O12B S1 C33 F11B -164.0(4) . . . . ? O23 S2 C34 F23B -177.2(4) . . . . ? O21 S2 C34 F23B 62.6(4) . . . . ? O22 S2 C34 F23B -57.0(4) . . . . ? O23 S2 C34 F21B -69.3(5) . . . . ? O21 S2 C34 F21B 170.5(5) . . . . ? O22 S2 C34 F21B 50.9(5) . . . . ? O23 S2 C34 F22A 76.9(6) . . . . ? O21 S2 C34 F22A -43.3(6) . . . . ? O22 S2 C34 F22A -162.9(5) . . . . ? O23 S2 C34 F22B 51.8(5) . . . . ? O21 S2 C34 F22B -68.4(5) . . . . ? O22 S2 C34 F22B 172.0(5) . . . . ? O23 S2 C34 F21A -48.2(4) . . . . ? O21 S2 C34 F21A -168.4(4) . . . . ? O22 S2 C34 F21A 72.1(4) . . . . ? O23 S2 C34 F23A -177.3(3) . . . . ? O21 S2 C34 F23A 62.5(3) . . . . ? O22 S2 C34 F23A -57.0(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 N8 H8C O1W 0.88 2.06 2.873(3) 153.1 . N12 H12B O1W 0.88 2.11 2.920(3) 151.9 . O1W H1WB N4 0.80(4) 2.11(4) 2.893(3) 166(3) . O1W H1WA N10 0.79(4) 2.19(4) 2.976(3) 174(3) . N13A H13B O5 0.92 1.85 2.759(4) 169.0 2_656 N13A H13A O11A 0.92 1.98 2.844(5) 156.0 2_556 N13B H13C O11B 0.92 2.40 2.991(13) 122.1 2_556 N13B H13C N11 0.92 2.66 3.334(10) 130.3 2_566 N13B H13D O21 0.92 2.07 2.953(12) 159.7 . N14 H14C O22 0.92 2.04 2.871(3) 149.6 2_666 N14 H14D O12B 0.92 2.09 2.813(7) 134.7 1_565 N14 H14D O8 0.92 2.31 2.889(3) 120.3 . N14 H14D O12A 0.92 2.35 3.093(5) 138.3 1_565 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.692 _refine_diff_density_min -0.706 _refine_diff_density_rms 0.061 # Attachment 'web_deposit_cif_file_1_AnnePetitjean_1312319103.ap17_July 2011.cif' data_ap17 _database_code_depnum_ccdc_archive 'CCDC 837813' #TrackingRef 'web_deposit_cif_file_1_AnnePetitjean_1312319103.ap17_July 2011.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C48 H44 N18 O13' _chemical_formula_weight 1081.01 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 Cc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 11.3994(2) _cell_length_b 17.3955(4) _cell_length_c 25.7476(5) _cell_angle_alpha 90.00 _cell_angle_beta 102.6120(10) _cell_angle_gamma 90.00 _cell_volume 4982.51(17) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 5025 _cell_measurement_theta_min 2.18 _cell_measurement_theta_max 21.22 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.441 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2248 _exptl_absorpt_coefficient_mu 0.109 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9786 _exptl_absorpt_correction_T_max 0.9892 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 35628 _diffrn_reflns_av_R_equivalents 0.0581 _diffrn_reflns_av_sigmaI/netI 0.0593 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 26.00 _reflns_number_total 9760 _reflns_number_gt 7115 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0459P)^2^+0.4069P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1.6(8) _refine_ls_number_reflns 9760 _refine_ls_number_parameters 718 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0742 _refine_ls_R_factor_gt 0.0443 _refine_ls_wR_factor_ref 0.1042 _refine_ls_wR_factor_gt 0.0898 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.016 _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 1.15999(19) 0.24795(11) 0.56266(8) 0.0403(5) Uani 1 1 d . . . O2 O 1.18385(19) 0.11369(12) 0.40650(8) 0.0432(5) Uani 1 1 d . . . O3 O 0.8459(2) 0.45184(12) 0.34322(8) 0.0448(6) Uani 1 1 d . . . O4 O 0.87982(18) 0.38606(12) 0.52315(8) 0.0406(5) Uani 1 1 d . . . O5 O 1.21164(19) 0.49586(12) 0.76364(8) 0.0455(6) Uani 1 1 d . . . O6 O 1.30109(18) 0.66407(11) 0.91009(8) 0.0383(5) Uani 1 1 d . . . O7 O 0.9705(2) 0.35327(12) 0.97671(8) 0.0428(5) Uani 1 1 d . . . O8 O 0.9252(2) 0.35918(13) 0.79049(8) 0.0472(6) Uani 1 1 d . . . O9 O 0.58338(18) 0.28435(12) 0.55753(8) 0.0413(5) Uani 1 1 d . . . O10 O 0.5913(2) 0.35399(12) 0.38176(8) 0.0444(5) Uani 1 1 d . . . O11 O 0.9504(2) 0.02558(12) 0.44773(9) 0.0482(6) Uani 1 1 d . . . O12 O 0.81104(18) 0.11323(12) 0.59557(8) 0.0413(5) Uani 1 1 d . . . N1 N 1.0135(2) 0.20730(14) 0.63746(9) 0.0349(6) Uani 1 1 d . . . N2 N 1.2174(2) 0.17643(15) 0.56145(10) 0.0454(7) Uani 1 1 d . . . N3 N 1.1421(2) 0.19433(14) 0.46952(9) 0.0356(6) Uani 1 1 d . . . H3B H 1.1031 0.2362 0.4749 0.043 Uiso 1 1 calc R . . N4 N 1.0146(2) 0.28576(13) 0.39312(9) 0.0291(5) Uani 1 1 d . . . N5 N 0.8826(2) 0.39709(13) 0.42565(9) 0.0314(6) Uani 1 1 d . . . H5A H 0.9194 0.3592 0.4454 0.038 Uiso 1 1 calc R . . N6 N 0.8111(2) 0.44814(14) 0.49710(10) 0.0387(6) Uani 1 1 d . . . N7 N 1.0247(2) 0.43157(14) 0.64204(9) 0.0379(6) Uani 1 1 d . . . N8 N 1.2727(3) 0.56682(16) 0.76547(11) 0.0497(7) Uani 1 1 d . . . N9 N 1.2360(2) 0.56636(13) 0.85262(9) 0.0318(5) Uani 1 1 d . . . H9A H 1.1974 0.5222 0.8480 0.038 Uiso 1 1 calc R . . N10 N 1.1262(2) 0.50043(12) 0.92478(9) 0.0274(5) Uani 1 1 d . . . N11 N 0.9735(2) 0.38214(13) 0.89078(9) 0.0304(6) Uani 1 1 d . . . H11B H 0.9970 0.4154 0.8694 0.036 Uiso 1 1 calc R . . N12 N 0.8800(2) 0.30183(14) 0.82006(10) 0.0396(6) Uani 1 1 d . . . N13 N 0.7024(2) 0.31200(15) 0.67269(10) 0.0419(7) Uani 1 1 d . . . N14 N 0.5335(2) 0.35291(15) 0.53200(10) 0.0412(6) Uani 1 1 d . . . N15 N 0.6174(2) 0.29972(14) 0.46414(9) 0.0335(6) Uani 1 1 d . . . H15B H 0.6487 0.2609 0.4844 0.040 Uiso 1 1 calc R . . N16 N 0.7622(2) 0.18985(14) 0.43437(9) 0.0322(6) Uani 1 1 d . . . N17 N 0.8751(2) 0.09078(15) 0.50975(9) 0.0375(6) Uani 1 1 d . . . H17A H 0.8372 0.1329 0.5157 0.045 Uiso 1 1 calc R . . N18 N 0.8881(2) 0.04817(15) 0.59715(10) 0.0415(6) Uani 1 1 d . . . C1 C 0.9626(3) 0.16243(17) 0.66877(11) 0.0346(7) Uani 1 1 d . . . C2 C 1.0267(3) 0.13274(18) 0.71654(12) 0.0399(8) Uani 1 1 d . . . H2A H 0.9874 0.1022 0.7382 0.048 Uiso 1 1 calc R . . C3 C 1.1463(3) 0.14766(19) 0.73226(12) 0.0427(8) Uani 1 1 d . . . H3A H 1.1922 0.1268 0.7644 0.051 Uiso 1 1 calc R . . C4 C 1.1997(3) 0.19428(18) 0.70004(12) 0.0419(8) Uani 1 1 d . . . H4A H 1.2829 0.2064 0.7102 0.050 Uiso 1 1 calc R . . C5 C 1.1306(3) 0.22280(16) 0.65305(11) 0.0331(7) Uani 1 1 d . . . C6 C 1.1833(3) 0.27409(18) 0.61717(12) 0.0432(8) Uani 1 1 d . . . H6A H 1.1497 0.3264 0.6181 0.052 Uiso 1 1 calc R . . H6B H 1.2713 0.2774 0.6310 0.052 Uiso 1 1 calc R . . C7 C 1.2036(3) 0.15422(18) 0.51316(12) 0.0408(8) Uani 1 1 d . . . H7A H 1.2385 0.1064 0.5069 0.049 Uiso 1 1 calc R . . C8 C 1.1385(3) 0.17248(17) 0.41845(12) 0.0336(7) Uani 1 1 d . . . C9 C 1.0760(3) 0.22806(16) 0.37682(11) 0.0317(7) Uani 1 1 d . . . C10 C 1.0871(3) 0.21910(18) 0.32483(12) 0.0378(7) Uani 1 1 d . . . H10A H 1.1304 0.1768 0.3151 0.045 Uiso 1 1 calc R . . C11 C 1.0342(3) 0.27255(19) 0.28714(12) 0.0410(8) Uani 1 1 d . . . H11A H 1.0404 0.2679 0.2511 0.049 Uiso 1 1 calc R . . C12 C 0.9720(3) 0.33321(18) 0.30356(11) 0.0370(7) Uani 1 1 d . . . H12A H 0.9361 0.3716 0.2789 0.044 Uiso 1 1 calc R . . C13 C 0.9630(2) 0.33716(16) 0.35613(11) 0.0305(6) Uani 1 1 d . . . C14 C 0.8913(3) 0.40097(17) 0.37350(12) 0.0343(7) Uani 1 1 d . . . C15 C 0.8195(3) 0.44935(17) 0.44858(12) 0.0341(7) Uani 1 1 d . . . H15A H 0.7791 0.4894 0.4267 0.041 Uiso 1 1 calc R . . C16 C 0.8585(3) 0.3790(2) 0.57643(12) 0.0465(9) Uani 1 1 d . . . H16A H 0.8919 0.3295 0.5920 0.056 Uiso 1 1 calc R . . H16B H 0.7708 0.3785 0.5745 0.056 Uiso 1 1 calc R . . C17 C 0.9150(3) 0.44416(18) 0.61222(12) 0.0395(8) Uani 1 1 d . . . C18 C 0.8557(3) 0.5130(2) 0.61484(13) 0.0571(10) Uani 1 1 d . . . H18A H 0.7763 0.5203 0.5945 0.068 Uiso 1 1 calc R . . C19 C 0.9135(4) 0.5713(2) 0.64745(14) 0.0636(11) Uani 1 1 d . . . H19A H 0.8761 0.6199 0.6484 0.076 Uiso 1 1 calc R . . C20 C 1.0250(4) 0.5575(2) 0.67807(13) 0.0566(10) Uani 1 1 d . . . H20A H 1.0661 0.5963 0.7011 0.068 Uiso 1 1 calc R . . C21 C 1.0769(3) 0.48727(17) 0.67523(12) 0.0383(7) Uani 1 1 d . . . C22 C 1.1953(3) 0.4644(2) 0.71042(12) 0.0490(9) Uani 1 1 d . . . H22A H 1.1998 0.4076 0.7127 0.059 Uiso 1 1 calc R . . H22B H 1.2615 0.4824 0.6942 0.059 Uiso 1 1 calc R . . C23 C 1.2811(3) 0.59647(19) 0.81120(12) 0.0405(8) Uani 1 1 d . . . H23A H 1.3226 0.6441 0.8176 0.049 Uiso 1 1 calc R . . C24 C 1.2495(2) 0.60327(16) 0.90039(11) 0.0280(6) Uani 1 1 d . . . C25 C 1.1940(2) 0.56294(15) 0.94065(10) 0.0261(6) Uani 1 1 d . . . C26 C 1.2143(3) 0.59176(17) 0.99219(11) 0.0343(7) Uani 1 1 d . . . H26A H 1.2616 0.6366 1.0017 0.041 Uiso 1 1 calc R . . C27 C 1.1645(3) 0.55412(17) 1.02929(11) 0.0343(7) Uani 1 1 d . . . H27A H 1.1775 0.5724 1.0649 0.041 Uiso 1 1 calc R . . C28 C 1.0952(3) 0.48913(16) 1.01384(11) 0.0332(7) Uani 1 1 d . . . H28A H 1.0602 0.4619 1.0387 0.040 Uiso 1 1 calc R . . C29 C 1.0779(2) 0.46469(16) 0.96160(11) 0.0301(6) Uani 1 1 d . . . C30 C 1.0026(3) 0.39469(16) 0.94458(11) 0.0310(7) Uani 1 1 d . . . C31 C 0.9085(3) 0.31865(17) 0.86940(12) 0.0334(7) Uani 1 1 d . . . H31A H 0.8827 0.2845 0.8934 0.040 Uiso 1 1 calc R . . C32 C 0.8863(3) 0.3400(3) 0.73534(12) 0.0581(10) Uani 1 1 d . . . H32A H 0.9012 0.2846 0.7306 0.070 Uiso 1 1 calc R . . H32B H 0.9349 0.3693 0.7147 0.070 Uiso 1 1 calc R . . C33 C 0.7551(3) 0.35671(19) 0.71335(12) 0.0426(8) Uani 1 1 d . . . C34 C 0.6926(4) 0.4149(2) 0.73259(14) 0.0546(9) Uani 1 1 d . . . H34A H 0.7312 0.4456 0.7619 0.066 Uiso 1 1 calc R . . C35 C 0.5743(4) 0.4275(2) 0.70860(16) 0.0646(11) Uani 1 1 d . . . H35A H 0.5295 0.4665 0.7214 0.078 Uiso 1 1 calc R . . C36 C 0.5213(4) 0.3824(2) 0.66534(14) 0.0553(9) Uani 1 1 d . . . H36A H 0.4401 0.3908 0.6475 0.066 Uiso 1 1 calc R . . C37 C 0.5873(3) 0.32597(19) 0.64887(12) 0.0407(8) Uani 1 1 d . . . C38 C 0.5339(3) 0.2723(2) 0.60341(13) 0.0474(8) Uani 1 1 d . . . H38A H 0.5488 0.2185 0.6155 0.057 Uiso 1 1 calc R . . H38B H 0.4458 0.2802 0.5935 0.057 Uiso 1 1 calc R . . C39 C 0.5559(3) 0.35526(18) 0.48561(12) 0.0381(7) Uani 1 1 d . . . H39A H 0.5279 0.3987 0.4641 0.046 Uiso 1 1 calc R . . C40 C 0.6321(3) 0.30222(17) 0.41302(12) 0.0344(7) Uani 1 1 d . . . C41 C 0.7025(3) 0.23748(16) 0.39692(11) 0.0318(7) Uani 1 1 d . . . C42 C 0.7030(3) 0.22929(18) 0.34339(12) 0.0399(8) Uani 1 1 d . . . H42A H 0.6579 0.2633 0.3177 0.048 Uiso 1 1 calc R . . C43 C 0.7698(3) 0.17095(19) 0.32809(12) 0.0433(8) Uani 1 1 d . . . H43A H 0.7710 0.1642 0.2916 0.052 Uiso 1 1 calc R . . C44 C 0.8345(3) 0.12281(17) 0.36569(12) 0.0382(8) Uani 1 1 d . . . H44A H 0.8833 0.0833 0.3562 0.046 Uiso 1 1 calc R . . C45 C 0.8263(3) 0.13374(16) 0.41852(12) 0.0327(7) Uani 1 1 d . . . C46 C 0.8914(3) 0.07835(18) 0.45955(12) 0.0376(7) Uani 1 1 d . . . C47 C 0.9143(3) 0.04127(18) 0.55181(13) 0.0406(8) Uani 1 1 d . . . H47A H 0.9641 -0.0006 0.5466 0.049 Uiso 1 1 calc R . . C48 C 0.8317(3) 0.1449(2) 0.64831(12) 0.0447(8) Uani 1 1 d . . . H48A H 0.8047 0.1078 0.6724 0.054 Uiso 1 1 calc R . . H48B H 0.7841 0.1926 0.6478 0.054 Uiso 1 1 calc R . . O1W O 0.5444(2) 0.50218(16) 0.32590(10) 0.0632(7) Uani 1 1 d D . . H1WB H 0.536(3) 0.4567(17) 0.3448(14) 0.076 Uiso 1 1 d D . . H1WA H 0.599(3) 0.539(2) 0.3468(14) 0.076 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 O1 0.0577(13) 0.0347(12) 0.0316(12) 0.0056(9) 0.0167(10) 0.0114(10) O2 0.0498(14) 0.0373(12) 0.0433(13) -0.0010(10) 0.0121(11) 0.0087(11) O3 0.0585(15) 0.0351(12) 0.0366(12) 0.0040(10) 0.0015(10) 0.0099(11) O4 0.0472(13) 0.0394(13) 0.0308(11) 0.0047(9) -0.0012(10) 0.0019(10) O5 0.0587(15) 0.0439(13) 0.0310(12) 0.0008(10) 0.0038(10) -0.0090(11) O6 0.0424(13) 0.0329(12) 0.0386(12) -0.0001(10) 0.0066(10) -0.0090(10) O7 0.0592(15) 0.0377(12) 0.0321(12) 0.0082(10) 0.0112(10) -0.0097(11) O8 0.0577(15) 0.0562(15) 0.0278(11) -0.0042(10) 0.0099(10) -0.0240(11) O9 0.0465(13) 0.0440(13) 0.0315(12) -0.0005(10) 0.0047(9) 0.0033(10) O10 0.0545(15) 0.0376(12) 0.0380(12) 0.0095(10) 0.0032(10) 0.0057(11) O11 0.0539(14) 0.0396(13) 0.0551(15) -0.0012(11) 0.0202(12) 0.0080(11) O12 0.0443(13) 0.0428(13) 0.0343(12) 0.0008(10) 0.0032(10) 0.0048(10) N1 0.0418(15) 0.0362(14) 0.0269(13) -0.0012(11) 0.0078(11) 0.0053(12) N2 0.0565(18) 0.0424(16) 0.0401(16) 0.0069(13) 0.0169(13) 0.0192(13) N3 0.0395(15) 0.0338(14) 0.0334(14) -0.0004(11) 0.0077(11) 0.0059(12) N4 0.0307(13) 0.0266(13) 0.0289(13) -0.0037(11) 0.0039(10) -0.0051(11) N5 0.0340(14) 0.0287(13) 0.0290(13) -0.0018(11) 0.0016(10) 0.0017(10) N6 0.0403(15) 0.0356(15) 0.0373(15) -0.0005(12) 0.0022(12) 0.0008(12) N7 0.0443(16) 0.0385(15) 0.0288(13) 0.0046(11) 0.0031(12) 0.0003(12) N8 0.0587(19) 0.0475(18) 0.0428(17) 0.0014(13) 0.0107(14) -0.0177(14) N9 0.0359(14) 0.0309(13) 0.0281(13) 0.0000(11) 0.0059(10) -0.0048(11) N10 0.0294(13) 0.0264(13) 0.0250(12) -0.0013(10) 0.0030(10) 0.0018(10) N11 0.0351(14) 0.0292(13) 0.0264(13) 0.0018(10) 0.0057(10) -0.0066(11) N12 0.0435(16) 0.0394(16) 0.0374(16) -0.0035(12) 0.0118(12) -0.0101(12) N13 0.0453(17) 0.0507(17) 0.0313(14) -0.0057(13) 0.0123(12) -0.0066(13) N14 0.0373(15) 0.0453(16) 0.0378(15) -0.0030(13) 0.0011(12) 0.0060(13) N15 0.0349(14) 0.0318(14) 0.0325(14) 0.0022(11) 0.0045(11) 0.0030(11) N16 0.0359(14) 0.0303(14) 0.0307(13) 0.0006(11) 0.0078(11) -0.0036(11) N17 0.0413(15) 0.0360(15) 0.0343(15) 0.0016(11) 0.0065(12) 0.0049(12) N18 0.0471(16) 0.0382(15) 0.0352(16) -0.0010(12) 0.0002(12) 0.0031(13) C1 0.0424(18) 0.0350(17) 0.0278(15) -0.0009(13) 0.0109(13) 0.0022(14) C2 0.053(2) 0.0377(18) 0.0304(17) 0.0013(14) 0.0111(15) 0.0029(15) C3 0.054(2) 0.047(2) 0.0257(16) 0.0004(14) 0.0061(15) 0.0092(16) C4 0.0449(19) 0.0448(19) 0.0333(17) -0.0110(15) 0.0027(14) 0.0068(15) C5 0.0394(18) 0.0291(17) 0.0312(17) -0.0017(13) 0.0087(14) 0.0050(14) C6 0.050(2) 0.0390(19) 0.0423(19) -0.0064(15) 0.0136(16) -0.0020(16) C7 0.049(2) 0.0403(18) 0.0345(18) 0.0053(15) 0.0124(15) 0.0171(15) C8 0.0312(16) 0.0346(17) 0.0364(17) -0.0013(14) 0.0101(13) -0.0038(14) C9 0.0338(16) 0.0268(15) 0.0336(16) -0.0017(13) 0.0055(13) -0.0032(13) C10 0.0364(18) 0.0404(18) 0.0361(17) -0.0095(14) 0.0072(14) -0.0014(15) C11 0.0434(19) 0.053(2) 0.0263(16) -0.0056(15) 0.0074(14) -0.0066(16) C12 0.0414(18) 0.0421(19) 0.0251(15) 0.0002(14) 0.0020(13) -0.0032(15) C13 0.0299(16) 0.0309(16) 0.0290(15) -0.0020(13) 0.0031(12) -0.0060(13) C14 0.0376(18) 0.0284(16) 0.0339(17) -0.0027(14) 0.0014(14) -0.0037(14) C15 0.0378(18) 0.0292(17) 0.0327(17) -0.0041(13) 0.0018(13) 0.0001(13) C16 0.046(2) 0.055(2) 0.0340(18) 0.0126(16) -0.0020(15) -0.0094(16) C17 0.046(2) 0.048(2) 0.0264(16) 0.0069(14) 0.0108(14) 0.0054(16) C18 0.053(2) 0.079(3) 0.0354(19) -0.0039(19) 0.0024(16) 0.024(2) C19 0.079(3) 0.065(3) 0.042(2) -0.0086(19) 0.002(2) 0.040(2) C20 0.074(3) 0.052(2) 0.040(2) -0.0101(17) 0.0018(18) 0.020(2) C21 0.051(2) 0.0338(18) 0.0296(16) -0.0003(14) 0.0069(14) 0.0041(15) C22 0.059(2) 0.043(2) 0.0378(19) -0.0102(15) -0.0049(16) 0.0055(17) C23 0.049(2) 0.044(2) 0.0299(17) -0.0011(15) 0.0105(14) -0.0095(15) C24 0.0260(15) 0.0295(16) 0.0264(15) -0.0001(13) 0.0012(12) 0.0036(13) C25 0.0277(15) 0.0264(15) 0.0227(14) -0.0004(12) 0.0023(11) 0.0045(12) C26 0.0344(16) 0.0317(16) 0.0348(17) -0.0043(14) 0.0029(13) 0.0017(13) C27 0.0429(18) 0.0381(18) 0.0225(15) -0.0050(13) 0.0083(13) 0.0038(15) C28 0.0379(17) 0.0343(17) 0.0283(16) 0.0024(13) 0.0095(13) 0.0029(14) C29 0.0317(16) 0.0287(15) 0.0288(16) 0.0012(12) 0.0044(12) 0.0047(12) C30 0.0339(16) 0.0285(16) 0.0308(16) 0.0002(13) 0.0076(13) 0.0044(13) C31 0.0328(16) 0.0330(17) 0.0347(18) 0.0047(13) 0.0080(13) -0.0051(14) C32 0.060(2) 0.088(3) 0.0264(18) -0.0081(18) 0.0095(16) -0.018(2) C33 0.053(2) 0.047(2) 0.0281(17) 0.0028(15) 0.0092(15) -0.0057(16) C34 0.080(3) 0.043(2) 0.0388(19) -0.0067(16) 0.0073(19) -0.001(2) C35 0.080(3) 0.047(2) 0.064(3) -0.0049(19) 0.008(2) 0.019(2) C36 0.064(2) 0.050(2) 0.047(2) 0.0007(18) 0.0028(18) 0.0134(19) C37 0.047(2) 0.045(2) 0.0324(16) 0.0063(15) 0.0146(15) -0.0024(16) C38 0.044(2) 0.055(2) 0.044(2) -0.0007(16) 0.0100(16) -0.0101(16) C39 0.0354(18) 0.0392(18) 0.0357(18) -0.0022(14) -0.0007(14) 0.0035(14) C40 0.0316(17) 0.0360(18) 0.0322(17) -0.0022(14) -0.0003(13) -0.0072(14) C41 0.0360(17) 0.0284(16) 0.0306(16) -0.0016(13) 0.0062(13) -0.0087(13) C42 0.051(2) 0.0381(18) 0.0295(17) 0.0024(14) 0.0069(15) -0.0100(15) C43 0.055(2) 0.046(2) 0.0300(17) -0.0039(15) 0.0118(15) -0.0128(17) C44 0.048(2) 0.0321(17) 0.0386(19) -0.0088(14) 0.0172(15) -0.0121(15) C45 0.0341(17) 0.0294(16) 0.0358(17) -0.0027(13) 0.0105(13) -0.0070(13) C46 0.0370(18) 0.0350(18) 0.0424(19) -0.0002(14) 0.0124(14) -0.0039(15) C47 0.0378(18) 0.0350(18) 0.044(2) -0.0013(15) -0.0030(15) 0.0008(15) C48 0.050(2) 0.054(2) 0.0329(18) -0.0027(15) 0.0137(15) -0.0045(16) O1W 0.0735(18) 0.0575(18) 0.0534(16) 0.0036(13) 0.0024(13) -0.0038(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 N2 1.409(3) . ? O1 C6 1.444(4) . ? O2 C8 1.216(3) . ? O3 C14 1.217(3) . ? O4 N6 1.414(3) . ? O4 C16 1.450(4) . ? O5 N8 1.413(3) . ? O5 C22 1.449(4) . ? O6 C24 1.209(3) . ? O7 C30 1.212(3) . ? O8 N12 1.418(3) . ? O8 C32 1.432(3) . ? O9 N14 1.419(3) . ? O9 C38 1.431(4) . ? O10 C40 1.229(3) . ? O11 C46 1.216(3) . ? O12 N18 1.428(3) . ? O12 C48 1.436(3) . ? N1 C5 1.335(4) . ? N1 C1 1.342(4) . ? N2 C7 1.279(4) . ? N3 C8 1.361(4) . ? N3 C7 1.378(4) . ? N3 H3B 0.8800 . ? N4 C9 1.342(4) . ? N4 C13 1.345(4) . ? N5 C14 1.369(4) . ? N5 C15 1.371(4) . ? N5 H5A 0.8800 . ? N6 C15 1.274(4) . ? N7 C17 1.335(4) . ? N7 C21 1.342(4) . ? N8 C23 1.270(4) . ? N9 C24 1.366(3) . ? N9 C23 1.384(4) . ? N9 H9A 0.8800 . ? N10 C25 1.345(3) . ? N10 C29 1.348(4) . ? N11 C30 1.370(3) . ? N11 C31 1.376(4) . ? N11 H11B 0.8800 . ? N12 C31 1.275(3) . ? N13 C33 1.337(4) . ? N13 C37 1.344(4) . ? N14 C39 1.276(4) . ? N15 C40 1.363(4) . ? N15 C39 1.378(4) . ? N15 H15B 0.8800 . ? N16 C45 1.335(4) . ? N16 C41 1.339(4) . ? N17 C46 1.363(4) . ? N17 C47 1.380(4) . ? N17 H17A 0.8800 . ? N18 C47 1.272(4) . ? C1 C2 1.386(4) . ? C1 C48 1.502(4) . ? C2 C3 1.359(4) . ? C2 H2A 0.9500 . ? C3 C4 1.392(5) . ? C3 H3A 0.9500 . ? C4 C5 1.384(4) . ? C4 H4A 0.9500 . ? C5 C6 1.500(4) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9500 . ? C8 C9 1.503(4) . ? C9 C10 1.381(4) . ? C10 C11 1.383(4) . ? C10 H10A 0.9500 . ? C11 C12 1.388(4) . ? C11 H11A 0.9500 . ? C12 C13 1.382(4) . ? C12 H12A 0.9500 . ? C13 C14 1.503(4) . ? C15 H15A 0.9500 . ? C16 C17 1.513(4) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.384(5) . ? C18 C19 1.388(5) . ? C18 H18A 0.9500 . ? C19 C20 1.362(5) . ? C19 H19A 0.9500 . ? C20 C21 1.367(4) . ? C20 H20A 0.9500 . ? C21 C22 1.506(4) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 H23A 0.9500 . ? C24 C25 1.501(4) . ? C25 C26 1.390(4) . ? C26 C27 1.378(4) . ? C26 H26A 0.9500 . ? C27 C28 1.387(4) . ? C27 H27A 0.9500 . ? C28 C29 1.383(4) . ? C28 H28A 0.9500 . ? C29 C30 1.499(4) . ? C31 H31A 0.9500 . ? C32 C33 1.508(5) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 C34 1.390(5) . ? C34 C35 1.373(5) . ? C34 H34A 0.9500 . ? C35 C36 1.389(5) . ? C35 H35A 0.9500 . ? C36 C37 1.360(5) . ? C36 H36A 0.9500 . ? C37 C38 1.517(4) . ? C38 H38A 0.9900 . ? C38 H38B 0.9900 . ? C39 H39A 0.9500 . ? C40 C41 1.494(4) . ? C41 C42 1.387(4) . ? C42 C43 1.377(5) . ? C42 H42A 0.9500 . ? C43 C44 1.367(4) . ? C43 H43A 0.9500 . ? C44 C45 1.397(4) . ? C44 H44A 0.9500 . ? C45 C46 1.501(4) . ? C47 H47A 0.9500 . ? C48 H48A 0.9900 . ? C48 H48B 0.9900 . ? O1W H1WB 0.95(2) . ? O1W H1WA 0.97(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 O1 C6 108.2(2) . . ? N6 O4 C16 108.9(2) . . ? N8 O5 C22 108.8(2) . . ? N12 O8 C32 107.3(2) . . ? N14 O9 C38 108.4(2) . . ? N18 O12 C48 107.7(2) . . ? C5 N1 C1 118.2(2) . . ? C7 N2 O1 109.2(2) . . ? C8 N3 C7 123.3(3) . . ? C8 N3 H3B 118.3 . . ? C7 N3 H3B 118.3 . . ? C9 N4 C13 117.0(2) . . ? C14 N5 C15 123.1(3) . . ? C14 N5 H5A 118.4 . . ? C15 N5 H5A 118.4 . . ? C15 N6 O4 109.0(2) . . ? C17 N7 C21 118.5(3) . . ? C23 N8 O5 108.8(3) . . ? C24 N9 C23 121.9(2) . . ? C24 N9 H9A 119.1 . . ? C23 N9 H9A 119.1 . . ? C25 N10 C29 117.1(2) . . ? C30 N11 C31 121.5(2) . . ? C30 N11 H11B 119.2 . . ? C31 N11 H11B 119.2 . . ? C31 N12 O8 109.3(2) . . ? C33 N13 C37 118.6(3) . . ? C39 N14 O9 108.6(2) . . ? C40 N15 C39 123.0(3) . . ? C40 N15 H15B 118.5 . . ? C39 N15 H15B 118.5 . . ? C45 N16 C41 117.3(2) . . ? C46 N17 C47 123.9(3) . . ? C46 N17 H17A 118.1 . . ? C47 N17 H17A 118.1 . . ? C47 N18 O12 108.4(2) . . ? N1 C1 C2 122.4(3) . . ? N1 C1 C48 115.8(3) . . ? C2 C1 C48 121.8(3) . . ? C3 C2 C1 119.6(3) . . ? C3 C2 H2A 120.2 . . ? C1 C2 H2A 120.2 . . ? C2 C3 C4 118.4(3) . . ? C2 C3 H3A 120.8 . . ? C4 C3 H3A 120.8 . . ? C5 C4 C3 119.3(3) . . ? C5 C4 H4A 120.3 . . ? C3 C4 H4A 120.3 . . ? N1 C5 C4 122.1(3) . . ? N1 C5 C6 116.3(3) . . ? C4 C5 C6 121.6(3) . . ? O1 C6 C5 113.4(2) . . ? O1 C6 H6A 108.9 . . ? C5 C6 H6A 108.9 . . ? O1 C6 H6B 108.9 . . ? C5 C6 H6B 108.9 . . ? H6A C6 H6B 107.7 . . ? N2 C7 N3 124.9(3) . . ? N2 C7 H7A 117.5 . . ? N3 C7 H7A 117.5 . . ? O2 C8 N3 123.7(3) . . ? O2 C8 C9 121.5(3) . . ? N3 C8 C9 114.8(3) . . ? N4 C9 C10 123.5(3) . . ? N4 C9 C8 117.2(2) . . ? C10 C9 C8 119.3(3) . . ? C9 C10 C11 119.1(3) . . ? C9 C10 H10A 120.5 . . ? C11 C10 H10A 120.5 . . ? C10 C11 C12 118.1(3) . . ? C10 C11 H11A 121.0 . . ? C12 C11 H11A 121.0 . . ? C13 C12 C11 119.3(3) . . ? C13 C12 H12A 120.4 . . ? C11 C12 H12A 120.4 . . ? N4 C13 C12 123.1(3) . . ? N4 C13 C14 117.6(2) . . ? C12 C13 C14 119.3(3) . . ? O3 C14 N5 123.5(3) . . ? O3 C14 C13 121.9(3) . . ? N5 C14 C13 114.6(3) . . ? N6 C15 N5 124.8(3) . . ? N6 C15 H15A 117.6 . . ? N5 C15 H15A 117.6 . . ? O4 C16 C17 112.1(2) . . ? O4 C16 H16A 109.2 . . ? C17 C16 H16A 109.2 . . ? O4 C16 H16B 109.2 . . ? C17 C16 H16B 109.2 . . ? H16A C16 H16B 107.9 . . ? N7 C17 C18 121.3(3) . . ? N7 C17 C16 116.6(3) . . ? C18 C17 C16 122.0(3) . . ? C17 C18 C19 119.3(3) . . ? C17 C18 H18A 120.4 . . ? C19 C18 H18A 120.4 . . ? C20 C19 C18 118.8(3) . . ? C20 C19 H19A 120.6 . . ? C18 C19 H19A 120.6 . . ? C19 C20 C21 119.1(3) . . ? C19 C20 H20A 120.5 . . ? C21 C20 H20A 120.5 . . ? N7 C21 C20 122.9(3) . . ? N7 C21 C22 114.0(3) . . ? C20 C21 C22 123.1(3) . . ? O5 C22 C21 112.5(3) . . ? O5 C22 H22A 109.1 . . ? C21 C22 H22A 109.1 . . ? O5 C22 H22B 109.1 . . ? C21 C22 H22B 109.1 . . ? H22A C22 H22B 107.8 . . ? N8 C23 N9 126.5(3) . . ? N8 C23 H23A 116.7 . . ? N9 C23 H23A 116.7 . . ? O6 C24 N9 123.4(3) . . ? O6 C24 C25 121.7(2) . . ? N9 C24 C25 114.9(2) . . ? N10 C25 C26 123.1(3) . . ? N10 C25 C24 118.0(2) . . ? C26 C25 C24 118.9(2) . . ? C27 C26 C25 118.9(3) . . ? C27 C26 H26A 120.6 . . ? C25 C26 H26A 120.6 . . ? C26 C27 C28 118.9(3) . . ? C26 C27 H27A 120.5 . . ? C28 C27 H27A 120.5 . . ? C29 C28 C27 118.7(3) . . ? C29 C28 H28A 120.6 . . ? C27 C28 H28A 120.6 . . ? N10 C29 C28 123.3(3) . . ? N10 C29 C30 117.7(2) . . ? C28 C29 C30 119.0(3) . . ? O7 C30 N11 123.6(3) . . ? O7 C30 C29 121.5(3) . . ? N11 C30 C29 115.0(2) . . ? N12 C31 N11 125.5(3) . . ? N12 C31 H31A 117.3 . . ? N11 C31 H31A 117.3 . . ? O8 C32 C33 113.2(3) . . ? O8 C32 H32A 108.9 . . ? C33 C32 H32A 108.9 . . ? O8 C32 H32B 108.9 . . ? C33 C32 H32B 108.9 . . ? H32A C32 H32B 107.7 . . ? N13 C33 C34 121.7(3) . . ? N13 C33 C32 114.9(3) . . ? C34 C33 C32 123.4(3) . . ? C35 C34 C33 119.1(3) . . ? C35 C34 H34A 120.5 . . ? C33 C34 H34A 120.5 . . ? C34 C35 C36 118.9(3) . . ? C34 C35 H35A 120.5 . . ? C36 C35 H35A 120.5 . . ? C37 C36 C35 119.0(4) . . ? C37 C36 H36A 120.5 . . ? C35 C36 H36A 120.5 . . ? N13 C37 C36 122.7(3) . . ? N13 C37 C38 115.4(3) . . ? C36 C37 C38 121.9(3) . . ? O9 C38 C37 112.5(3) . . ? O9 C38 H38A 109.1 . . ? C37 C38 H38A 109.1 . . ? O9 C38 H38B 109.1 . . ? C37 C38 H38B 109.1 . . ? H38A C38 H38B 107.8 . . ? N14 C39 N15 125.2(3) . . ? N14 C39 H39A 117.4 . . ? N15 C39 H39A 117.4 . . ? O10 C40 N15 123.2(3) . . ? O10 C40 C41 121.3(3) . . ? N15 C40 C41 115.5(3) . . ? N16 C41 C42 122.7(3) . . ? N16 C41 C40 119.1(2) . . ? C42 C41 C40 118.2(3) . . ? C43 C42 C41 118.8(3) . . ? C43 C42 H42A 120.6 . . ? C41 C42 H42A 120.6 . . ? C44 C43 C42 119.7(3) . . ? C44 C43 H43A 120.2 . . ? C42 C43 H43A 120.2 . . ? C43 C44 C45 117.8(3) . . ? C43 C44 H44A 121.1 . . ? C45 C44 H44A 121.1 . . ? N16 C45 C44 123.7(3) . . ? N16 C45 C46 118.3(3) . . ? C44 C45 C46 118.0(3) . . ? O11 C46 N17 123.7(3) . . ? O11 C46 C45 121.6(3) . . ? N17 C46 C45 114.6(3) . . ? N18 C47 N17 124.1(3) . . ? N18 C47 H47A 118.0 . . ? N17 C47 H47A 118.0 . . ? O12 C48 C1 110.8(2) . . ? O12 C48 H48A 109.5 . . ? C1 C48 H48A 109.5 . . ? O12 C48 H48B 109.5 . . ? C1 C48 H48B 109.5 . . ? H48A C48 H48B 108.1 . . ? H1WB O1W H1WA 113(3) . . ? 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 C6 O1 N2 C7 -176.4(3) . . . . ? C16 O4 N6 C15 -173.1(2) . . . . ? C22 O5 N8 C23 176.4(3) . . . . ? C32 O8 N12 C31 -177.3(3) . . . . ? C38 O9 N14 C39 -166.0(2) . . . . ? C48 O12 N18 C47 -150.3(3) . . . . ? C5 N1 C1 C2 0.8(4) . . . . ? C5 N1 C1 C48 -178.1(3) . . . . ? N1 C1 C2 C3 -1.5(5) . . . . ? C48 C1 C2 C3 177.2(3) . . . . ? C1 C2 C3 C4 1.6(5) . . . . ? C2 C3 C4 C5 -0.9(4) . . . . ? C1 N1 C5 C4 -0.1(4) . . . . ? C1 N1 C5 C6 -179.2(2) . . . . ? C3 C4 C5 N1 0.2(4) . . . . ? C3 C4 C5 C6 179.2(3) . . . . ? N2 O1 C6 C5 -63.7(3) . . . . ? N1 C5 C6 O1 -53.3(4) . . . . ? C4 C5 C6 O1 127.6(3) . . . . ? O1 N2 C7 N3 -0.1(4) . . . . ? C8 N3 C7 N2 173.8(3) . . . . ? C7 N3 C8 O2 3.9(5) . . . . ? C7 N3 C8 C9 -174.6(3) . . . . ? C13 N4 C9 C10 -0.7(4) . . . . ? C13 N4 C9 C8 177.3(2) . . . . ? O2 C8 C9 N4 171.1(3) . . . . ? N3 C8 C9 N4 -10.4(4) . . . . ? O2 C8 C9 C10 -10.8(4) . . . . ? N3 C8 C9 C10 167.7(3) . . . . ? N4 C9 C10 C11 1.1(4) . . . . ? C8 C9 C10 C11 -176.9(3) . . . . ? C9 C10 C11 C12 0.0(4) . . . . ? C10 C11 C12 C13 -1.3(4) . . . . ? C9 N4 C13 C12 -0.8(4) . . . . ? C9 N4 C13 C14 178.5(2) . . . . ? C11 C12 C13 N4 1.8(4) . . . . ? C11 C12 C13 C14 -177.5(3) . . . . ? C15 N5 C14 O3 1.5(4) . . . . ? C15 N5 C14 C13 -179.0(2) . . . . ? N4 C13 C14 O3 176.8(3) . . . . ? C12 C13 C14 O3 -3.9(4) . . . . ? N4 C13 C14 N5 -2.7(4) . . . . ? C12 C13 C14 N5 176.6(2) . . . . ? O4 N6 C15 N5 1.7(4) . . . . ? C14 N5 C15 N6 -178.9(3) . . . . ? N6 O4 C16 C17 -70.9(3) . . . . ? C21 N7 C17 C18 0.4(4) . . . . ? C21 N7 C17 C16 -178.5(3) . . . . ? O4 C16 C17 N7 -94.2(3) . . . . ? O4 C16 C17 C18 86.9(4) . . . . ? N7 C17 C18 C19 2.8(5) . . . . ? C16 C17 C18 C19 -178.4(3) . . . . ? C17 C18 C19 C20 -3.3(6) . . . . ? C18 C19 C20 C21 0.8(6) . . . . ? C17 N7 C21 C20 -3.0(5) . . . . ? C17 N7 C21 C22 174.8(3) . . . . ? C19 C20 C21 N7 2.4(5) . . . . ? C19 C20 C21 C22 -175.2(3) . . . . ? N8 O5 C22 C21 -92.4(3) . . . . ? N7 C21 C22 O5 -142.2(3) . . . . ? C20 C21 C22 O5 35.6(5) . . . . ? O5 N8 C23 N9 -1.6(5) . . . . ? C24 N9 C23 N8 -179.7(3) . . . . ? C23 N9 C24 O6 0.0(4) . . . . ? C23 N9 C24 C25 179.4(2) . . . . ? C29 N10 C25 C26 -0.7(4) . . . . ? C29 N10 C25 C24 179.5(2) . . . . ? O6 C24 C25 N10 172.3(3) . . . . ? N9 C24 C25 N10 -7.2(3) . . . . ? O6 C24 C25 C26 -7.5(4) . . . . ? N9 C24 C25 C26 173.1(2) . . . . ? N10 C25 C26 C27 1.1(4) . . . . ? C24 C25 C26 C27 -179.2(3) . . . . ? C25 C26 C27 C28 -0.5(4) . . . . ? C26 C27 C28 C29 -0.4(4) . . . . ? C25 N10 C29 C28 -0.2(4) . . . . ? C25 N10 C29 C30 -179.7(2) . . . . ? C27 C28 C29 N10 0.7(4) . . . . ? C27 C28 C29 C30 -179.7(3) . . . . ? C31 N11 C30 O7 -2.6(4) . . . . ? C31 N11 C30 C29 177.7(2) . . . . ? N10 C29 C30 O7 169.3(3) . . . . ? C28 C29 C30 O7 -10.3(4) . . . . ? N10 C29 C30 N11 -11.0(4) . . . . ? C28 C29 C30 N11 169.5(3) . . . . ? O8 N12 C31 N11 -0.4(4) . . . . ? C30 N11 C31 N12 -178.4(3) . . . . ? N12 O8 C32 C33 75.0(4) . . . . ? C37 N13 C33 C34 2.4(5) . . . . ? C37 N13 C33 C32 -176.4(3) . . . . ? O8 C32 C33 N13 -151.9(3) . . . . ? O8 C32 C33 C34 29.3(5) . . . . ? N13 C33 C34 C35 -1.1(5) . . . . ? C32 C33 C34 C35 177.6(3) . . . . ? C33 C34 C35 C36 -0.9(5) . . . . ? C34 C35 C36 C37 1.5(6) . . . . ? C33 N13 C37 C36 -1.8(5) . . . . ? C33 N13 C37 C38 -179.5(3) . . . . ? C35 C36 C37 N13 -0.1(5) . . . . ? C35 C36 C37 C38 177.4(3) . . . . ? N14 O9 C38 C37 -74.9(3) . . . . ? N13 C37 C38 O9 -70.2(4) . . . . ? C36 C37 C38 O9 112.0(4) . . . . ? O9 N14 C39 N15 0.6(4) . . . . ? C40 N15 C39 N14 175.4(3) . . . . ? C39 N15 C40 O10 -0.3(4) . . . . ? C39 N15 C40 C41 179.3(2) . . . . ? C45 N16 C41 C42 1.6(4) . . . . ? C45 N16 C41 C40 -178.5(2) . . . . ? O10 C40 C41 N16 168.7(3) . . . . ? N15 C40 C41 N16 -10.9(4) . . . . ? O10 C40 C41 C42 -11.4(4) . . . . ? N15 C40 C41 C42 169.0(3) . . . . ? N16 C41 C42 C43 -1.6(4) . . . . ? C40 C41 C42 C43 178.5(3) . . . . ? C41 C42 C43 C44 -0.3(5) . . . . ? C42 C43 C44 C45 2.1(5) . . . . ? C41 N16 C45 C44 0.4(4) . . . . ? C41 N16 C45 C46 -178.4(2) . . . . ? C43 C44 C45 N16 -2.2(4) . . . . ? C43 C44 C45 C46 176.6(3) . . . . ? C47 N17 C46 O11 -6.1(5) . . . . ? C47 N17 C46 C45 171.7(3) . . . . ? N16 C45 C46 O11 179.4(3) . . . . ? C44 C45 C46 O11 0.5(4) . . . . ? N16 C45 C46 N17 1.5(4) . . . . ? C44 C45 C46 N17 -177.4(3) . . . . ? O12 N18 C47 N17 1.4(4) . . . . ? C46 N17 C47 N18 -172.0(3) . . . . ? N18 O12 C48 C1 54.7(3) . . . . ? N1 C1 C48 O12 53.9(3) . . . . ? C2 C1 C48 O12 -124.9(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 O1W H1WB O10 0.95(2) 2.06(3) 2.943(3) 155(3) . O1W H1WA O2 0.97(3) 2.09(3) 3.026(4) 163(3) 3_455 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.234 _refine_diff_density_min -0.165 _refine_diff_density_rms 0.040