# Supplementary Material (ESI) for Organic and Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2010 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Scott Stewart' _publ_contact_author_email SGS@CYLLENE.UWA.EDU.AU _publ_section_title ; Formation and reactions of azepino[4,5-b]indoles: An unprecedented ozone reaction in the formation of novel benzo[c]naphthyridinones ; loop_ _publ_author_name 'Scott Stewart' 'Emilio L. Ghisalberti' 'Charles H. Heath' 'Brian W Skelton' data_ch3964 _database_code_depnum_ccdc_archive 'CCDC 767164' #TrackingRef 'ch3964.cif' _audit_creation_date 2009-09-03T16:34:41-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C16 H13 F3 N2 O3' _chemical_formula_moiety 'C16 H13 F3 N2 O3' _chemical_formula_weight 338.28 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall -P_1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.7998(5) _cell_length_b 8.4873(5) _cell_length_c 11.8596(6) _cell_angle_alpha 72.423(5) _cell_angle_beta 80.473(5) _cell_angle_gamma 72.510(6) _cell_volume 711.42(7) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4486 _cell_measurement_theta_min 3.5472 _cell_measurement_theta_max 34.7631 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_max 0.68 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.12 _exptl_crystal_density_diffrn 1.579 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 348 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.136 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.83836 _exptl_absorpt_correction_T_max 1 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 10.4738 _diffrn_orient_matrix_ub_11 -0.0253407019 _diffrn_orient_matrix_ub_12 0.0813185258 _diffrn_orient_matrix_ub_13 0.0119040646 _diffrn_orient_matrix_ub_21 -0.0069610651 _diffrn_orient_matrix_ub_22 -0.040338316 _diffrn_orient_matrix_ub_23 0.061766651 _diffrn_orient_matrix_ub_31 0.0919778341 _diffrn_orient_matrix_ub_32 -0.005635459 _diffrn_orient_matrix_ub_33 0.0024715915 _diffrn_measurement_device_type 'Oxford Diffraction Gemini, Ruby' _diffrn_measurement_method '\w scans' _diffrn_reflns_av_R_equivalents 0.0363 _diffrn_reflns_av_unetI/netI 0.0587 _diffrn_reflns_number 10493 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.55 _diffrn_reflns_theta_max 34.85 _diffrn_reflns_theta_full 33 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.92 _reflns_number_total 5697 _reflns_number_gt 3855 _reflns_threshold_expression I>2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'OrtepII (Johnson, C. K. (1976)' _computing_publication_material 'WinGX Farrugia, L. J. (1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^ > 2\s(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^)+(0.0667P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 5697 _refine_ls_number_parameters 218 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0712 _refine_ls_R_factor_gt 0.0451 _refine_ls_wR_factor_ref 0.1197 _refine_ls_wR_factor_gt 0.1117 _refine_ls_goodness_of_fit_ref 0.948 _refine_ls_restrained_S_all 0.948 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.507 _refine_diff_density_min -0.326 _refine_diff_density_rms 0.067 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.57087(14) 0.31691(15) 0.07613(9) 0.0157(2) Uani 1 1 d . . . O1 O 0.68883(10) 0.36596(12) 0.00838(7) 0.01975(18) Uani 1 1 d . . . O2 O 0.52862(10) 0.33971(11) 0.18752(7) 0.01630(16) Uani 1 1 d . . . C2A C 0.37498(14) 0.26991(15) 0.24879(9) 0.01380(19) Uani 1 1 d . . . C2A1 C 0.44203(15) 0.13138(16) 0.35907(9) 0.0174(2) Uani 1 1 d . . . H2A1 H 0.5501 0.048 0.337 0.026 Uiso 1 1 calc R . . H2A2 H 0.3479 0.0732 0.3972 0.026 Uiso 1 1 calc R . . H2A3 H 0.4714 0.1833 0.4143 0.026 Uiso 1 1 calc R . . C3 C 0.21890(14) 0.41832(15) 0.27574(9) 0.0148(2) Uani 1 1 d . . . H3A H 0.2538 0.4632 0.334 0.018 Uiso 1 1 calc R . . H3B H 0.1941 0.5124 0.2021 0.018 Uiso 1 1 calc R . . N4 N 0.05487(12) 0.36054(12) 0.32374(8) 0.01390(17) Uani 1 1 d . . . C4 C 0.02075(15) 0.32019(15) 0.44312(9) 0.0154(2) Uani 1 1 d . . . O4 O 0.12022(12) 0.31777(12) 0.51327(7) 0.02135(18) Uani 1 1 d . . . C41 C -0.15792(15) 0.27136(16) 0.49520(10) 0.0183(2) Uani 1 1 d . . . F41 F -0.16664(10) 0.22761(11) 0.61367(6) 0.02632(18) Uani 1 1 d . . . F42 F -0.30531(9) 0.39941(10) 0.46292(7) 0.02449(17) Uani 1 1 d . . . F43 F -0.17100(10) 0.13544(10) 0.46410(6) 0.02335(17) Uani 1 1 d . . . C5 C -0.06130(14) 0.35305(15) 0.23910(9) 0.0154(2) Uani 1 1 d . . . H5A H -0.0668 0.4534 0.1691 0.018 Uiso 1 1 calc R . . H5B H -0.1852 0.361 0.2776 0.018 Uiso 1 1 calc R . . C6 C 0.00551(14) 0.18892(15) 0.19724(9) 0.0151(2) Uani 1 1 d . . . H6A H 0.0216 0.0876 0.267 0.018 Uiso 1 1 calc R . . H6B H -0.0858 0.1837 0.1505 0.018 Uiso 1 1 calc R . . C6A C 0.18126(14) 0.18456(15) 0.12243(9) 0.0142(2) Uani 1 1 d . . . C6B C 0.22231(15) 0.18477(14) -0.00204(9) 0.0148(2) Uani 1 1 d . . . C7 C 0.12299(16) 0.17163(15) -0.08562(10) 0.0171(2) Uani 1 1 d . . . H7 H 0.0089 0.1476 -0.0626 0.02 Uiso 1 1 calc R . . C8 C 0.19504(17) 0.19455(16) -0.20281(10) 0.0203(2) Uani 1 1 d . . . H8 H 0.1287 0.1868 -0.2604 0.024 Uiso 1 1 calc R . . C9 C 0.36421(17) 0.22896(16) -0.23790(10) 0.0208(2) Uani 1 1 d . . . H9 H 0.4087 0.2462 -0.319 0.025 Uiso 1 1 calc R . . C10 C 0.46754(16) 0.23831(15) -0.15684(10) 0.0188(2) Uani 1 1 d . . . H10 H 0.5834 0.2583 -0.1799 0.023 Uiso 1 1 calc R . . C10A C 0.39326(15) 0.21700(15) -0.04027(9) 0.0156(2) Uani 1 1 d . . . N10B N 0.45819(12) 0.22896(13) 0.05943(8) 0.01507(18) Uani 1 1 d . . . C10C C 0.32688(14) 0.21138(14) 0.15394(9) 0.0137(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0134(4) 0.0185(5) 0.0123(4) -0.0009(4) -0.0026(4) -0.0026(4) O1 0.0140(4) 0.0262(5) 0.0156(4) -0.0011(3) 0.0003(3) -0.0058(3) O2 0.0154(4) 0.0229(4) 0.0119(3) -0.0032(3) -0.0003(3) -0.0090(3) C2A 0.0136(4) 0.0186(5) 0.0099(4) -0.0020(4) 0.0002(3) -0.0076(4) C2A1 0.0183(5) 0.0204(6) 0.0119(4) -0.0016(4) -0.0032(4) -0.0046(4) C3 0.0157(5) 0.0169(5) 0.0126(4) -0.0034(4) -0.0002(4) -0.0066(4) N4 0.0142(4) 0.0175(5) 0.0103(4) -0.0040(3) -0.0001(3) -0.0049(3) C4 0.0183(5) 0.0163(5) 0.0114(4) -0.0039(4) 0.0006(4) -0.0048(4) O4 0.0239(4) 0.0294(5) 0.0128(3) -0.0064(3) -0.0023(3) -0.0090(4) C41 0.0203(5) 0.0211(6) 0.0129(4) -0.0040(4) 0.0006(4) -0.0062(4) F41 0.0294(4) 0.0357(5) 0.0116(3) -0.0034(3) 0.0039(3) -0.0112(3) F42 0.0180(3) 0.0281(4) 0.0229(3) -0.0061(3) 0.0020(3) -0.0022(3) F43 0.0256(4) 0.0243(4) 0.0225(3) -0.0066(3) 0.0030(3) -0.0123(3) C5 0.0150(5) 0.0194(5) 0.0118(4) -0.0035(4) -0.0032(4) -0.0041(4) C6 0.0153(5) 0.0197(5) 0.0117(4) -0.0044(4) -0.0017(4) -0.0061(4) C6A 0.0151(5) 0.0164(5) 0.0107(4) -0.0035(4) -0.0021(3) -0.0032(4) C6B 0.0183(5) 0.0142(5) 0.0115(4) -0.0038(4) -0.0021(4) -0.0027(4) C7 0.0209(5) 0.0171(5) 0.0143(4) -0.0051(4) -0.0040(4) -0.0044(4) C8 0.0290(6) 0.0192(6) 0.0130(5) -0.0057(4) -0.0054(4) -0.0035(5) C9 0.0307(6) 0.0191(6) 0.0109(4) -0.0050(4) 0.0009(4) -0.0046(5) C10 0.0222(5) 0.0190(6) 0.0129(4) -0.0050(4) 0.0028(4) -0.0036(4) C10A 0.0186(5) 0.0162(5) 0.0109(4) -0.0041(4) -0.0017(4) -0.0026(4) N10B 0.0153(4) 0.0196(5) 0.0097(4) -0.0032(3) -0.0001(3) -0.0048(3) C10C 0.0149(5) 0.0167(5) 0.0085(4) -0.0022(4) -0.0003(3) -0.0045(4) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.2037(13) . ? C1 O2 1.3649(13) . ? C1 N10B 1.3821(15) . ? O2 C2A 1.4810(13) . ? C2A C10C 1.4974(15) . ? C2A C2A1 1.5148(15) . ? C2A C3 1.5373(15) . ? C2A1 H2A1 0.98 . ? C2A1 H2A2 0.98 . ? C2A1 H2A3 0.98 . ? C3 N4 1.4727(14) . ? C3 H3A 0.99 . ? C3 H3B 0.99 . ? N4 C4 1.3527(13) . ? N4 C5 1.4857(13) . ? C4 O4 1.2199(13) . ? C4 C41 1.5502(16) . ? C41 F41 1.3361(12) . ? C41 F42 1.3389(14) . ? C41 F43 1.3481(14) . ? C5 C6 1.5343(16) . ? C5 H5A 0.99 . ? C5 H5B 0.99 . ? C6 C6A 1.5014(15) . ? C6 H6A 0.99 . ? C6 H6B 0.99 . ? C6A C10C 1.3523(15) . ? C6A C6B 1.4574(14) . ? C6B C7 1.4028(15) . ? C6B C10A 1.4151(16) . ? C7 C8 1.3890(15) . ? C7 H7 0.95 . ? C8 C9 1.4056(18) . ? C8 H8 0.95 . ? C9 C10 1.3861(16) . ? C9 H9 0.95 . ? C10 C10A 1.3879(15) . ? C10 H10 0.95 . ? C10A N10B 1.4023(14) . ? N10B C10C 1.3922(13) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 O2 123.54(10) . . ? O1 C1 N10B 128.41(10) . . ? O2 C1 N10B 108.05(9) . . ? C1 O2 C2A 111.28(8) . . ? O2 C2A C10C 101.51(8) . . ? O2 C2A C2A1 107.16(8) . . ? C10C C2A C2A1 116.28(10) . . ? O2 C2A C3 108.37(9) . . ? C10C C2A C3 109.22(8) . . ? C2A1 C2A C3 113.36(9) . . ? C2A C2A1 H2A1 109.5 . . ? C2A C2A1 H2A2 109.5 . . ? H2A1 C2A1 H2A2 109.5 . . ? C2A C2A1 H2A3 109.5 . . ? H2A1 C2A1 H2A3 109.5 . . ? H2A2 C2A1 H2A3 109.5 . . ? N4 C3 C2A 110.79(9) . . ? N4 C3 H3A 109.5 . . ? C2A C3 H3A 109.5 . . ? N4 C3 H3B 109.5 . . ? C2A C3 H3B 109.5 . . ? H3A C3 H3B 108.1 . . ? C4 N4 C3 116.60(9) . . ? C4 N4 C5 124.96(9) . . ? C3 N4 C5 118.44(8) . . ? O4 C4 N4 125.17(10) . . ? O4 C4 C41 117.30(9) . . ? N4 C4 C41 117.53(9) . . ? F41 C41 F42 106.77(9) . . ? F41 C41 F43 106.64(9) . . ? F42 C41 F43 107.44(9) . . ? F41 C41 C4 109.88(9) . . ? F42 C41 C4 113.41(10) . . ? F43 C41 C4 112.33(9) . . ? N4 C5 C6 113.36(9) . . ? N4 C5 H5A 108.9 . . ? C6 C5 H5A 108.9 . . ? N4 C5 H5B 108.9 . . ? C6 C5 H5B 108.9 . . ? H5A C5 H5B 107.7 . . ? C6A C6 C5 110.76(9) . . ? C6A C6 H6A 109.5 . . ? C5 C6 H6A 109.5 . . ? C6A C6 H6B 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 108.1 . . ? C10C C6A C6B 105.42(9) . . ? C10C C6A C6 124.53(9) . . ? C6B C6A C6 129.09(9) . . ? C7 C6B C10A 118.58(9) . . ? C7 C6B C6A 132.82(10) . . ? C10A C6B C6A 108.42(9) . . ? C8 C7 C6B 118.54(11) . . ? C8 C7 H7 120.7 . . ? C6B C7 H7 120.7 . . ? C7 C8 C9 121.29(10) . . ? C7 C8 H8 119.4 . . ? C9 C8 H8 119.4 . . ? C10 C9 C8 121.50(10) . . ? C10 C9 H9 119.3 . . ? C8 C9 H9 119.3 . . ? C9 C10 C10A 116.65(11) . . ? C9 C10 H10 121.7 . . ? C10A C10 H10 121.7 . . ? C10 C10A N10B 130.27(11) . . ? C10 C10A C6B 123.41(10) . . ? N10B C10A C6B 106.27(9) . . ? C1 N10B C10C 110.87(9) . . ? C1 N10B C10A 134.43(9) . . ? C10C N10B C10A 108.27(9) . . ? C6A C10C N10B 111.56(9) . . ? C6A C10C C2A 138.77(10) . . ? N10B C10C C2A 107.57(9) . . ? data_ch4651 _database_code_depnum_ccdc_archive 'CCDC 767165' #TrackingRef 'ch4651.cif' _audit_creation_date 2009-09-17T20:53:38-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C15 H15 F3 N2 O4' _chemical_formula_moiety 'C15 H15 F3 N2 O4' _chemical_formula_weight 344.29 _chemical_absolute_configuration unk #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 10.0807(2) _cell_length_b 19.0872(4) _cell_length_c 22.9900(5) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 4423.56(16) _cell_formula_units_Z 12 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 21572 _cell_measurement_theta_min 3.6548 _cell_measurement_theta_max 32.5828 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.14 _exptl_crystal_density_diffrn 1.551 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2136 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.137 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.97567 _exptl_absorpt_correction_T_max 1 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 10.4738 _diffrn_orient_matrix_ub_11 -0.0056560125 _diffrn_orient_matrix_ub_12 -0.0222328825 _diffrn_orient_matrix_ub_13 -0.0246585819 _diffrn_orient_matrix_ub_21 -0.0285675179 _diffrn_orient_matrix_ub_22 -0.0264659535 _diffrn_orient_matrix_ub_23 0.0177020127 _diffrn_orient_matrix_ub_31 -0.0640510718 _diffrn_orient_matrix_ub_32 0.0137338226 _diffrn_orient_matrix_ub_33 -0.0057109293 _diffrn_measurement_device_type 'Oxford Diffraction Gemini, Ruby' _diffrn_measurement_method '\w scans' _diffrn_reflns_av_R_equivalents 0.0425 _diffrn_reflns_av_unetI/netI 0.0447 _diffrn_reflns_number 59406 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 3.66 _diffrn_reflns_theta_max 32.64 _diffrn_reflns_theta_full 31.5 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.958 _reflns_number_total 8485 _reflns_number_gt 6891 _reflns_threshold_expression I>2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'OrtepII (Johnson, C. K. (1976)' _computing_publication_material 'WinGX Farrugia, L. J. (1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^ > 2\s(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^)+(0.0411P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 8485 _refine_ls_number_parameters 673 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.051 _refine_ls_R_factor_gt 0.0372 _refine_ls_wR_factor_ref 0.0789 _refine_ls_wR_factor_gt 0.0768 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_Flack ? _refine_diff_density_max 0.307 _refine_diff_density_min -0.209 _refine_diff_density_rms 0.05 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' 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 C11 C 0.33757(17) 0.38160(9) 0.35479(7) 0.0146(3) Uani 1 1 d . . . H11A H 0.3017 0.4287 0.3636 0.018 Uiso 1 1 calc R . . H11B H 0.3617 0.3805 0.3131 0.018 Uiso 1 1 calc R . . C12 C 0.23034(17) 0.32699(10) 0.36616(7) 0.0162(3) Uani 1 1 d . . . H12A H 0.149 0.3394 0.3443 0.019 Uiso 1 1 calc R . . H12B H 0.261 0.2806 0.3525 0.019 Uiso 1 1 calc R . . N13 N 0.20029(14) 0.32365(8) 0.42879(6) 0.0140(3) Uani 1 1 d . . . C13 C 0.07984(17) 0.32706(9) 0.45424(8) 0.0166(3) Uani 1 1 d . . . O13 O 0.05798(13) 0.32265(7) 0.50606(6) 0.0226(3) Uani 1 1 d . . . C131 C -0.04058(19) 0.33935(12) 0.41438(10) 0.0275(5) Uani 1 1 d . . . F131 F -0.05523(12) 0.29064(8) 0.37321(6) 0.0362(3) Uani 1 1 d . . . F132 F -0.02993(14) 0.40130(8) 0.38687(7) 0.0460(4) Uani 1 1 d . . . F133 F -0.15091(12) 0.34063(9) 0.44503(7) 0.0475(4) Uani 1 1 d . . . C14 C 0.31590(16) 0.31064(9) 0.46579(7) 0.0134(3) Uani 1 1 d . . . H14A H 0.3526 0.2637 0.4569 0.016 Uiso 1 1 calc R . . H14B H 0.2882 0.311 0.5071 0.016 Uiso 1 1 calc R . . C14A C 0.42339(15) 0.36596(8) 0.45640(7) 0.0107(3) Uani 1 1 d . . . C15 C 0.37437(17) 0.43828(9) 0.47603(7) 0.0132(3) Uani 1 1 d . . . O15 O 0.27850(12) 0.44511(6) 0.50836(6) 0.0176(3) Uani 1 1 d . . . N16 N 0.44536(15) 0.49409(7) 0.45723(7) 0.0162(3) Uani 1 1 d . . . H16 H 0.4277 0.5353 0.4726 0.019 Uiso 1 1 calc R . . C16A C 0.54576(17) 0.49055(9) 0.41458(7) 0.0140(3) Uani 1 1 d . . . C17 C 0.62993(18) 0.54775(9) 0.40572(8) 0.0178(4) Uani 1 1 d . . . H17 H 0.6192 0.5893 0.4279 0.021 Uiso 1 1 calc R . . C18 C 0.72862(18) 0.54316(10) 0.36439(9) 0.0197(4) Uani 1 1 d . . . H18 H 0.7859 0.5819 0.358 0.024 Uiso 1 1 calc R . . C19 C 0.74499(17) 0.48194(10) 0.33187(8) 0.0178(4) Uani 1 1 d . . . H19 H 0.8135 0.479 0.3036 0.021 Uiso 1 1 calc R . . C110 C 0.66103(17) 0.42538(10) 0.34094(8) 0.0160(3) Uani 1 1 d . . . H110 H 0.6726 0.3837 0.3189 0.019 Uiso 1 1 calc R . . C111 C 0.56011(16) 0.42917(9) 0.38203(7) 0.0129(3) Uani 1 1 d . . . C112 C 0.46293(16) 0.36932(9) 0.39152(7) 0.0119(3) Uani 1 1 d . . . O112 O 0.52474(13) 0.30473(7) 0.37707(6) 0.0166(3) Uani 1 1 d D . . H112 H 0.487(2) 0.2878(13) 0.3482(9) 0.039(7) Uiso 1 1 d D . . C113 C 0.54581(17) 0.34683(9) 0.49306(7) 0.0139(3) Uani 1 1 d . . . H11C H 0.5856 0.3028 0.4784 0.017 Uiso 1 1 calc R . . H11D H 0.6131 0.3844 0.4901 0.017 Uiso 1 1 calc R . . O113 O 0.50597(13) 0.33823(8) 0.55228(6) 0.0216(3) Uani 1 1 d D . . H113 H 0.577(2) 0.3398(13) 0.5723(10) 0.037(7) Uiso 1 1 d D . . C21 C 0.13401(17) 0.66233(9) 0.66369(7) 0.0130(3) Uani 1 1 d . . . H21A H 0.0609 0.6588 0.6923 0.016 Uiso 1 1 calc R . . H21B H 0.1732 0.6151 0.659 0.016 Uiso 1 1 calc R . . C22 C 0.23933(17) 0.71201(10) 0.68713(7) 0.0150(3) Uani 1 1 d . . . H22A H 0.199 0.7582 0.6957 0.018 Uiso 1 1 calc R . . H22B H 0.2769 0.693 0.7237 0.018 Uiso 1 1 calc R . . N23 N 0.34561(14) 0.72028(7) 0.64343(6) 0.0127(3) Uani 1 1 d . . . C23 C 0.47552(17) 0.70673(9) 0.64948(7) 0.0145(3) Uani 1 1 d . . . O23 O 0.55864(12) 0.71220(7) 0.61129(6) 0.0186(3) Uani 1 1 d . . . C231 C 0.52308(19) 0.68355(12) 0.71033(8) 0.0238(4) Uani 1 1 d . . . F231 F 0.49566(13) 0.73168(8) 0.75085(5) 0.0336(3) Uani 1 1 d . . . F232 F 0.46898(13) 0.62315(7) 0.72747(6) 0.0349(3) Uani 1 1 d . . . F233 F 0.65359(11) 0.67479(9) 0.71019(6) 0.0403(4) Uani 1 1 d . . . C24 C 0.29712(16) 0.74737(9) 0.58781(7) 0.0115(3) Uani 1 1 d . . . H24A H 0.3725 0.7524 0.5605 0.014 Uiso 1 1 calc R . . H24B H 0.2577 0.7943 0.5939 0.014 Uiso 1 1 calc R . . C24A C 0.19315(16) 0.69864(8) 0.56111(7) 0.0104(3) Uani 1 1 d . . . C25 C 0.25672(16) 0.62802(9) 0.54461(7) 0.0122(3) Uani 1 1 d . . . O25 O 0.37548(12) 0.62349(7) 0.53169(6) 0.0170(3) Uani 1 1 d . . . N26 N 0.17535(14) 0.57278(7) 0.54103(6) 0.0136(3) Uani 1 1 d . . . H26 H 0.2106 0.5321 0.5319 0.016 Uiso 1 1 calc R . . C26A C 0.03741(17) 0.57500(9) 0.55075(7) 0.0134(3) Uani 1 1 d . . . C27 C -0.04186(19) 0.52074(9) 0.53023(8) 0.0176(4) Uani 1 1 d . . . H27 H -0.0034 0.4821 0.5104 0.021 Uiso 1 1 calc R . . C28 C -0.17842(19) 0.52385(10) 0.53914(8) 0.0205(4) Uani 1 1 d . . . H28 H -0.2336 0.4871 0.5254 0.025 Uiso 1 1 calc R . . C29 C -0.23408(18) 0.58047(10) 0.56803(8) 0.0191(4) Uani 1 1 d . . . H29 H -0.3274 0.5826 0.5736 0.023 Uiso 1 1 calc R . . C210 C -0.15377(17) 0.63427(9) 0.58887(8) 0.0156(3) Uani 1 1 d . . . H210 H -0.1925 0.6728 0.6087 0.019 Uiso 1 1 calc R . . C211 C -0.01706(17) 0.63182(9) 0.58076(7) 0.0125(3) Uani 1 1 d . . . C212 C 0.07734(16) 0.68657(8) 0.60485(7) 0.0109(3) Uani 1 1 d . . . O212 O 0.01008(12) 0.75100(6) 0.61681(6) 0.0146(2) Uani 1 1 d D . . H212 H 0.007(2) 0.7746(11) 0.5878(8) 0.022(6) Uiso 1 1 d D . . C213 C 0.14582(18) 0.72998(8) 0.50304(7) 0.0140(3) Uani 1 1 d . . . H21C H 0.2225 0.7372 0.4768 0.017 Uiso 1 1 calc R . . H21D H 0.083 0.6975 0.4839 0.017 Uiso 1 1 calc R . . O213 O 0.08220(13) 0.79526(6) 0.51430(6) 0.0172(3) Uani 1 1 d D . . H213 H 0.054(2) 0.8082(11) 0.4849(7) 0.014(5) Uiso 1 1 d D . . C31 C 0.51134(17) 0.02836(9) 0.26207(8) 0.0152(3) Uani 1 1 d . . . H31A H 0.4732 0.058 0.2309 0.018 Uiso 1 1 calc R . . H31B H 0.5322 -0.018 0.2451 0.018 Uiso 1 1 calc R . . C32 C 0.40963(17) 0.01928(9) 0.30994(8) 0.0167(3) Uani 1 1 d . . . H32A H 0.3256 0.0016 0.2931 0.02 Uiso 1 1 calc R . . H32B H 0.442 -0.0157 0.3384 0.02 Uiso 1 1 calc R . . N33 N 0.38512(14) 0.08654(8) 0.33979(7) 0.0151(3) Uani 1 1 d . . . C33 C 0.26692(18) 0.11441(10) 0.35162(8) 0.0168(3) Uani 1 1 d . . . O33 O 0.24600(13) 0.16133(7) 0.38699(6) 0.0222(3) Uani 1 1 d . . . C331 C 0.14747(19) 0.08968(11) 0.31499(9) 0.0231(4) Uani 1 1 d . . . F331 F 0.10692(13) 0.02465(7) 0.32883(7) 0.0393(3) Uani 1 1 d . . . F332 F 0.17538(12) 0.09006(7) 0.25825(5) 0.0314(3) Uani 1 1 d . . . F333 F 0.04562(11) 0.13234(7) 0.32264(6) 0.0346(3) Uani 1 1 d . . . C34 C 0.50482(16) 0.11975(10) 0.36405(8) 0.0143(3) Uani 1 1 d . . . H34A H 0.5443 0.089 0.3941 0.017 Uiso 1 1 calc R . . H34B H 0.481 0.1648 0.3826 0.017 Uiso 1 1 calc R . . C34A C 0.60596(16) 0.13258(9) 0.31509(7) 0.0118(3) Uani 1 1 d . . . C35 C 0.54865(16) 0.18385(9) 0.27046(7) 0.0133(3) Uani 1 1 d . . . O35 O 0.46154(13) 0.22685(7) 0.28226(6) 0.0179(3) Uani 1 1 d . . . N36 N 0.60232(15) 0.18151(8) 0.21646(6) 0.0159(3) Uani 1 1 d . . . H36 H 0.5721 0.2114 0.1905 0.019 Uiso 1 1 calc R . . C36A C 0.70277(17) 0.13492(9) 0.19889(7) 0.0149(3) Uani 1 1 d . . . C37 C 0.7731(2) 0.14800(10) 0.14808(8) 0.0221(4) Uani 1 1 d . . . H37 H 0.7532 0.1879 0.125 0.027 Uiso 1 1 calc R . . C38 C 0.8735(2) 0.10176(11) 0.13125(9) 0.0245(4) Uani 1 1 d . . . H38 H 0.9218 0.1099 0.0964 0.029 Uiso 1 1 calc R . . C39 C 0.90252(19) 0.04430(11) 0.16523(9) 0.0233(4) Uani 1 1 d . . . H39 H 0.9713 0.0132 0.1539 0.028 Uiso 1 1 calc R . . C310 C 0.83141(17) 0.03160(9) 0.21625(8) 0.0178(4) Uani 1 1 d . . . H310 H 0.8526 -0.0079 0.2396 0.021 Uiso 1 1 calc R . . C311 C 0.72973(17) 0.07647(9) 0.23301(7) 0.0139(3) Uani 1 1 d . . . C312 C 0.64049(16) 0.06235(9) 0.28432(8) 0.0134(3) Uani 1 1 d . . . O312 O 0.69660(13) 0.01281(7) 0.32367(6) 0.0178(3) Uani 1 1 d D . . H312 H 0.7473(19) 0.0372(10) 0.3433(8) 0.012(5) Uiso 1 1 d D . . C313 C 0.72964(17) 0.16901(9) 0.34109(8) 0.0155(3) Uani 1 1 d . . . H31C H 0.7925 0.182 0.3098 0.019 Uiso 1 1 calc R . . H31D H 0.7034 0.2121 0.3621 0.019 Uiso 1 1 calc R . . O313 O 0.78986(14) 0.12057(8) 0.38004(6) 0.0246(3) Uani 1 1 d D . . H313 H 0.852(2) 0.1380(13) 0.3999(11) 0.042(8) 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 C11 0.0152(8) 0.0174(8) 0.0113(8) 0.0007(6) -0.0013(6) -0.0001(6) C12 0.0158(8) 0.0222(9) 0.0105(8) 0.0005(7) -0.0022(6) -0.0031(7) N13 0.0138(7) 0.0153(7) 0.0129(7) 0.0003(5) -0.0013(5) -0.0008(6) C13 0.0160(8) 0.0122(8) 0.0217(9) -0.0002(7) 0.0008(7) -0.0006(6) O13 0.0208(7) 0.0270(7) 0.0200(7) -0.0012(6) 0.0059(5) -0.0015(6) C131 0.0157(9) 0.0337(11) 0.0331(12) 0.0137(9) -0.0007(8) -0.0005(8) F131 0.0273(6) 0.0554(9) 0.0258(7) 0.0068(6) -0.0095(5) -0.0155(6) F132 0.0313(7) 0.0412(8) 0.0655(10) 0.0290(7) -0.0038(7) 0.0087(6) F133 0.0149(6) 0.0803(11) 0.0472(9) 0.0173(8) 0.0059(6) 0.0083(7) C14 0.0140(8) 0.0138(8) 0.0124(8) 0.0000(6) -0.0021(6) -0.0007(6) C14A 0.0112(7) 0.0087(7) 0.0121(7) -0.0014(6) -0.0003(6) 0.0020(6) C15 0.0160(8) 0.0128(8) 0.0110(8) -0.0007(6) -0.0010(6) 0.0009(6) O15 0.0197(6) 0.0136(6) 0.0194(6) -0.0020(5) 0.0069(5) 0.0033(5) N16 0.0211(7) 0.0089(6) 0.0187(7) -0.0027(5) 0.0074(6) 0.0002(6) C16A 0.0148(8) 0.0141(8) 0.0133(8) 0.0007(6) 0.0006(6) 0.0012(6) C17 0.0204(9) 0.0141(8) 0.0189(9) -0.0001(7) -0.0004(7) 0.0002(7) C18 0.0151(8) 0.0201(9) 0.0240(9) 0.0078(7) -0.0015(7) -0.0050(7) C19 0.0118(8) 0.0253(9) 0.0164(9) 0.0037(7) 0.0010(6) 0.0009(7) C110 0.0139(8) 0.0205(9) 0.0136(8) -0.0013(7) -0.0006(6) 0.0034(7) C111 0.0119(7) 0.0145(8) 0.0123(8) 0.0026(6) -0.0014(6) 0.0007(6) C112 0.0130(7) 0.0101(7) 0.0125(8) -0.0016(6) 0.0008(6) 0.0022(6) O112 0.0188(6) 0.0139(6) 0.0170(6) -0.0064(5) 0.0002(5) 0.0038(5) C113 0.0132(8) 0.0159(8) 0.0126(8) -0.0002(6) -0.0001(6) 0.0009(6) O113 0.0162(6) 0.0367(8) 0.0118(6) 0.0009(6) -0.0014(5) 0.0018(6) C21 0.0143(8) 0.0143(8) 0.0102(8) 0.0011(6) 0.0017(6) 0.0009(6) C22 0.0134(8) 0.0220(9) 0.0096(7) -0.0017(6) 0.0029(6) -0.0007(7) N23 0.0132(7) 0.0161(7) 0.0086(6) -0.0006(5) 0.0013(5) 0.0001(5) C23 0.0169(8) 0.0138(8) 0.0128(8) 0.0011(6) -0.0011(6) -0.0007(6) O23 0.0148(6) 0.0254(7) 0.0156(6) 0.0020(5) 0.0027(5) 0.0000(5) C231 0.0176(9) 0.0360(11) 0.0178(9) 0.0073(8) -0.0011(7) -0.0001(8) F231 0.0304(6) 0.0549(8) 0.0154(6) -0.0061(5) -0.0040(5) -0.0061(6) F232 0.0356(7) 0.0362(7) 0.0329(7) 0.0202(6) 0.0004(6) 0.0012(6) F233 0.0163(6) 0.0778(10) 0.0266(7) 0.0185(7) -0.0029(5) 0.0078(6) C24 0.0130(7) 0.0111(7) 0.0105(7) 0.0007(6) 0.0008(6) 0.0006(6) C24A 0.0141(7) 0.0091(7) 0.0081(7) -0.0003(5) 0.0013(6) 0.0022(6) C25 0.0175(8) 0.0102(7) 0.0088(7) 0.0000(6) 0.0023(6) 0.0016(6) O25 0.0153(6) 0.0147(6) 0.0209(7) -0.0018(5) 0.0081(5) 0.0003(5) N26 0.0151(7) 0.0094(6) 0.0162(7) -0.0029(5) 0.0042(6) 0.0025(5) C26A 0.0148(7) 0.0134(8) 0.0119(8) 0.0015(6) 0.0005(6) 0.0016(6) C27 0.0226(9) 0.0134(8) 0.0169(9) -0.0016(6) -0.0013(7) -0.0003(7) C28 0.0213(9) 0.0186(9) 0.0216(9) 0.0009(7) -0.0058(8) -0.0051(7) C29 0.0139(8) 0.0197(9) 0.0237(9) 0.0040(7) -0.0031(7) -0.0009(7) C210 0.0147(8) 0.0148(8) 0.0174(8) 0.0015(7) -0.0004(6) 0.0032(6) C211 0.0154(8) 0.0118(8) 0.0103(7) 0.0012(6) -0.0004(6) 0.0008(6) C212 0.0112(7) 0.0103(7) 0.0112(7) 0.0000(6) 0.0027(6) 0.0026(6) O212 0.0178(6) 0.0113(6) 0.0146(6) -0.0018(5) 0.0018(5) 0.0053(5) C213 0.0198(8) 0.0119(8) 0.0104(8) 0.0011(6) -0.0006(6) 0.0010(6) O213 0.0245(7) 0.0129(6) 0.0142(6) 0.0023(5) -0.0041(5) 0.0045(5) C31 0.0156(8) 0.0139(8) 0.0160(8) -0.0035(6) 0.0004(7) -0.0004(6) C32 0.0156(8) 0.0137(8) 0.0208(9) -0.0020(7) 0.0023(7) -0.0032(7) N33 0.0126(7) 0.0172(7) 0.0154(7) -0.0015(6) 0.0015(6) -0.0020(5) C33 0.0154(8) 0.0196(9) 0.0154(8) 0.0012(7) 0.0022(7) -0.0026(7) O33 0.0189(6) 0.0270(7) 0.0207(7) -0.0061(6) 0.0059(5) -0.0010(6) C331 0.0159(9) 0.0307(11) 0.0228(10) -0.0077(8) 0.0014(7) 0.0003(8) F331 0.0254(6) 0.0370(8) 0.0556(9) -0.0016(7) -0.0046(6) -0.0143(6) F332 0.0239(6) 0.0500(8) 0.0204(6) -0.0115(5) -0.0036(5) 0.0071(6) F333 0.0180(6) 0.0520(8) 0.0338(7) -0.0144(6) -0.0033(5) 0.0118(6) C34 0.0129(8) 0.0181(8) 0.0120(8) 0.0002(6) 0.0006(6) -0.0026(6) C34A 0.0122(7) 0.0125(8) 0.0106(7) -0.0003(6) -0.0023(6) -0.0003(6) C35 0.0132(7) 0.0137(8) 0.0129(8) -0.0019(6) -0.0019(6) -0.0013(6) O35 0.0181(6) 0.0191(6) 0.0166(6) -0.0038(5) -0.0023(5) 0.0054(5) N36 0.0194(7) 0.0157(7) 0.0126(7) 0.0030(6) -0.0002(6) 0.0065(6) C36A 0.0147(8) 0.0149(8) 0.0150(8) -0.0019(6) 0.0001(6) 0.0022(6) C37 0.0255(9) 0.0232(10) 0.0177(9) 0.0049(7) 0.0050(8) 0.0055(8) C38 0.0246(10) 0.0297(11) 0.0192(10) 0.0040(8) 0.0078(8) 0.0038(8) C39 0.0170(9) 0.0254(10) 0.0274(10) -0.0036(8) 0.0049(8) 0.0042(8) C310 0.0169(8) 0.0165(9) 0.0202(9) 0.0012(7) -0.0003(7) 0.0042(7) C311 0.0135(7) 0.0140(8) 0.0141(8) -0.0007(6) -0.0007(6) -0.0014(6) C312 0.0132(7) 0.0126(8) 0.0142(8) 0.0030(6) -0.0014(6) 0.0016(6) O312 0.0167(6) 0.0170(6) 0.0197(7) 0.0063(5) -0.0031(5) 0.0020(5) C313 0.0115(7) 0.0189(9) 0.0161(8) -0.0009(7) -0.0021(6) -0.0013(6) O313 0.0213(7) 0.0292(8) 0.0233(7) 0.0074(6) -0.0120(6) -0.0051(6) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C11 C12 1.524(2) . ? C11 C112 1.538(2) . ? C11 H11A 0.99 . ? C11 H11B 0.99 . ? C12 N13 1.473(2) . ? C12 H12A 0.99 . ? C12 H12B 0.99 . ? N13 C13 1.349(2) . ? N13 C14 1.464(2) . ? C13 O13 1.214(2) . ? C13 C131 1.539(3) . ? C131 F133 1.317(2) . ? C131 F131 1.335(3) . ? C131 F132 1.345(2) . ? C14 C14A 1.528(2) . ? C14 H14A 0.99 . ? C14 H14B 0.99 . ? C14A C15 1.534(2) . ? C14A C113 1.538(2) . ? C14A C112 1.545(2) . ? C15 O15 1.226(2) . ? C15 N16 1.354(2) . ? N16 C16A 1.411(2) . ? N16 H16 0.88 . ? C16A C111 1.398(2) . ? C16A C17 1.398(2) . ? C17 C18 1.378(3) . ? C17 H17 0.95 . ? C18 C19 1.397(3) . ? C18 H18 0.95 . ? C19 C110 1.388(3) . ? C19 H19 0.95 . ? C110 C111 1.390(2) . ? C110 H110 0.95 . ? C111 C112 1.521(2) . ? C112 O112 1.421(2) . ? O112 H112 0.831(17) . ? C113 O113 1.429(2) . ? C113 H11C 0.99 . ? C113 H11D 0.99 . ? O113 H113 0.852(17) . ? C21 C22 1.522(2) . ? C21 C212 1.540(2) . ? C21 H21A 0.99 . ? C21 H21B 0.99 . ? C22 N23 1.477(2) . ? C22 H22A 0.99 . ? C22 H22B 0.99 . ? N23 C23 1.342(2) . ? N23 C24 1.463(2) . ? C23 O23 1.218(2) . ? C23 C231 1.544(3) . ? C231 F233 1.326(2) . ? C231 F232 1.335(2) . ? C231 F231 1.337(2) . ? C24 C24A 1.530(2) . ? C24 H24A 0.99 . ? C24 H24B 0.99 . ? C24A C213 1.539(2) . ? C24A C25 1.540(2) . ? C24A C212 1.558(2) . ? C25 O25 1.236(2) . ? C25 N26 1.338(2) . ? N26 C26A 1.409(2) . ? N26 H26 0.88 . ? C26A C27 1.391(2) . ? C26A C211 1.398(2) . ? C27 C28 1.393(3) . ? C27 H27 0.95 . ? C28 C29 1.387(3) . ? C28 H28 0.95 . ? C29 C210 1.393(3) . ? C29 H29 0.95 . ? C210 C211 1.391(2) . ? C210 H210 0.95 . ? C211 C212 1.518(2) . ? C212 O212 1.4309(19) . ? O212 H212 0.806(16) . ? C213 O213 1.425(2) . ? C213 H21C 0.99 . ? C213 H21D 0.99 . ? O213 H213 0.774(15) . ? C31 C32 1.514(2) . ? C31 C312 1.542(2) . ? C31 H31A 0.99 . ? C31 H31B 0.99 . ? C32 N33 1.477(2) . ? C32 H32A 0.99 . ? C32 H32B 0.99 . ? N33 C33 1.333(2) . ? N33 C34 1.473(2) . ? C33 O33 1.228(2) . ? C33 C331 1.543(3) . ? C331 F333 1.322(2) . ? C331 F332 1.334(2) . ? C331 F331 1.345(3) . ? C34 C34A 1.538(2) . ? C34 H34A 0.99 . ? C34 H34B 0.99 . ? C34A C35 1.531(2) . ? C34A C313 1.548(2) . ? C34A C312 1.555(2) . ? C35 O35 1.232(2) . ? C35 N36 1.355(2) . ? N36 C36A 1.407(2) . ? N36 H36 0.88 . ? C36A C37 1.389(3) . ? C36A C311 1.391(2) . ? C37 C38 1.397(3) . ? C37 H37 0.95 . ? C38 C39 1.378(3) . ? C38 H38 0.95 . ? C39 C310 1.396(3) . ? C39 H39 0.95 . ? C310 C311 1.390(2) . ? C310 H310 0.95 . ? C311 C312 1.508(2) . ? C312 O312 1.426(2) . ? O312 H312 0.826(15) . ? C313 O313 1.423(2) . ? C313 H31C 0.99 . ? C313 H31D 0.99 . ? O313 H313 0.843(17) . ? 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 C12 C11 C112 112.61(14) . . ? C12 C11 H11A 109.1 . . ? C112 C11 H11A 109.1 . . ? C12 C11 H11B 109.1 . . ? C112 C11 H11B 109.1 . . ? H11A C11 H11B 107.8 . . ? N13 C12 C11 110.07(14) . . ? N13 C12 H12A 109.6 . . ? C11 C12 H12A 109.6 . . ? N13 C12 H12B 109.6 . . ? C11 C12 H12B 109.6 . . ? H12A C12 H12B 108.2 . . ? C13 N13 C14 118.20(14) . . ? C13 N13 C12 127.36(15) . . ? C14 N13 C12 114.31(13) . . ? O13 C13 N13 125.82(17) . . ? O13 C13 C131 116.85(16) . . ? N13 C13 C131 117.32(16) . . ? F133 C131 F131 107.39(17) . . ? F133 C131 F132 107.61(18) . . ? F131 C131 F132 106.73(18) . . ? F133 C131 C13 110.51(17) . . ? F131 C131 C13 113.78(17) . . ? F132 C131 C13 110.55(17) . . ? N13 C14 C14A 111.42(13) . . ? N13 C14 H14A 109.3 . . ? C14A C14 H14A 109.3 . . ? N13 C14 H14B 109.3 . . ? C14A C14 H14B 109.3 . . ? H14A C14 H14B 108 . . ? C14 C14A C15 110.59(13) . . ? C14 C14A C113 109.10(13) . . ? C15 C14A C113 108.12(13) . . ? C14 C14A C112 110.36(13) . . ? C15 C14A C112 109.25(13) . . ? C113 C14A C112 109.38(13) . . ? O15 C15 N16 121.76(15) . . ? O15 C15 C14A 121.86(15) . . ? N16 C15 C14A 116.34(14) . . ? C15 N16 C16A 124.28(14) . . ? C15 N16 H16 117.9 . . ? C16A N16 H16 117.9 . . ? C111 C16A C17 120.92(16) . . ? C111 C16A N16 119.12(15) . . ? C17 C16A N16 119.96(15) . . ? C18 C17 C16A 119.27(17) . . ? C18 C17 H17 120.4 . . ? C16A C17 H17 120.4 . . ? C17 C18 C19 120.49(17) . . ? C17 C18 H18 119.8 . . ? C19 C18 H18 119.8 . . ? C110 C19 C18 119.88(17) . . ? C110 C19 H19 120.1 . . ? C18 C19 H19 120.1 . . ? C19 C110 C111 120.54(16) . . ? C19 C110 H110 119.7 . . ? C111 C110 H110 119.7 . . ? C110 C111 C16A 118.89(16) . . ? C110 C111 C112 122.00(15) . . ? C16A C111 C112 119.09(15) . . ? O112 C112 C111 109.62(13) . . ? O112 C112 C11 111.36(14) . . ? C111 C112 C11 109.63(13) . . ? O112 C112 C14A 107.63(13) . . ? C111 C112 C14A 109.63(13) . . ? C11 C112 C14A 108.93(13) . . ? C112 O112 H112 108.9(18) . . ? O113 C113 C14A 108.89(13) . . ? O113 C113 H11C 109.9 . . ? C14A C113 H11C 109.9 . . ? O113 C113 H11D 109.9 . . ? C14A C113 H11D 109.9 . . ? H11C C113 H11D 108.3 . . ? C113 O113 H113 105.9(17) . . ? C22 C21 C212 112.50(14) . . ? C22 C21 H21A 109.1 . . ? C212 C21 H21A 109.1 . . ? C22 C21 H21B 109.1 . . ? C212 C21 H21B 109.1 . . ? H21A C21 H21B 107.8 . . ? N23 C22 C21 109.37(14) . . ? N23 C22 H22A 109.8 . . ? C21 C22 H22A 109.8 . . ? N23 C22 H22B 109.8 . . ? C21 C22 H22B 109.8 . . ? H22A C22 H22B 108.2 . . ? C23 N23 C24 118.99(14) . . ? C23 N23 C22 128.07(15) . . ? C24 N23 C22 112.94(13) . . ? O23 C23 N23 125.44(16) . . ? O23 C23 C231 117.66(16) . . ? N23 C23 C231 116.89(15) . . ? F233 C231 F232 107.29(17) . . ? F233 C231 F231 107.06(17) . . ? F232 C231 F231 107.65(16) . . ? F233 C231 C23 110.00(16) . . ? F232 C231 C23 112.85(16) . . ? F231 C231 C23 111.72(16) . . ? N23 C24 C24A 111.38(13) . . ? N23 C24 H24A 109.4 . . ? C24A C24 H24A 109.4 . . ? N23 C24 H24B 109.4 . . ? C24A C24 H24B 109.4 . . ? H24A C24 H24B 108 . . ? C24 C24A C213 108.91(13) . . ? C24 C24A C25 110.24(13) . . ? C213 C24A C25 104.80(13) . . ? C24 C24A C212 110.14(13) . . ? C213 C24A C212 112.65(13) . . ? C25 C24A C212 109.97(13) . . ? O25 C25 N26 121.57(15) . . ? O25 C25 C24A 121.56(15) . . ? N26 C25 C24A 116.72(14) . . ? C25 N26 C26A 124.85(14) . . ? C25 N26 H26 117.6 . . ? C26A N26 H26 117.6 . . ? C27 C26A C211 121.30(16) . . ? C27 C26A N26 119.40(15) . . ? C211 C26A N26 119.30(15) . . ? C26A C27 C28 119.09(17) . . ? C26A C27 H27 120.5 . . ? C28 C27 H27 120.5 . . ? C29 C28 C27 120.23(17) . . ? C29 C28 H28 119.9 . . ? C27 C28 H28 119.9 . . ? C28 C29 C210 120.27(17) . . ? C28 C29 H29 119.9 . . ? C210 C29 H29 119.9 . . ? C211 C210 C29 120.32(17) . . ? C211 C210 H210 119.8 . . ? C29 C210 H210 119.8 . . ? C210 C211 C26A 118.77(16) . . ? C210 C211 C212 123.29(16) . . ? C26A C211 C212 117.90(15) . . ? O212 C212 C211 111.39(13) . . ? O212 C212 C21 105.38(13) . . ? C211 C212 C21 110.26(13) . . ? O212 C212 C24A 110.62(13) . . ? C211 C212 C24A 109.64(13) . . ? C21 C212 C24A 109.47(13) . . ? C212 O212 H212 109.7(16) . . ? O213 C213 C24A 108.78(13) . . ? O213 C213 H21C 109.9 . . ? C24A C213 H21C 109.9 . . ? O213 C213 H21D 109.9 . . ? C24A C213 H21D 109.9 . . ? H21C C213 H21D 108.3 . . ? C213 O213 H213 106.7(16) . . ? C32 C31 C312 112.26(14) . . ? C32 C31 H31A 109.2 . . ? C312 C31 H31A 109.2 . . ? C32 C31 H31B 109.2 . . ? C312 C31 H31B 109.2 . . ? H31A C31 H31B 107.9 . . ? N33 C32 C31 110.59(14) . . ? N33 C32 H32A 109.5 . . ? C31 C32 H32A 109.5 . . ? N33 C32 H32B 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 108.1 . . ? C33 N33 C34 118.90(14) . . ? C33 N33 C32 126.26(15) . . ? C34 N33 C32 114.41(14) . . ? O33 C33 N33 125.43(17) . . ? O33 C33 C331 116.77(16) . . ? N33 C33 C331 117.65(16) . . ? F333 C331 F332 106.87(17) . . ? F333 C331 F331 107.51(16) . . ? F332 C331 F331 107.48(16) . . ? F333 C331 C33 110.18(15) . . ? F332 C331 C33 111.55(16) . . ? F331 C331 C33 112.98(17) . . ? N33 C34 C34A 109.54(13) . . ? N33 C34 H34A 109.8 . . ? C34A C34 H34A 109.8 . . ? N33 C34 H34B 109.8 . . ? C34A C34 H34B 109.8 . . ? H34A C34 H34B 108.2 . . ? C35 C34A C34 110.00(13) . . ? C35 C34A C313 106.00(13) . . ? C34 C34A C313 108.84(13) . . ? C35 C34A C312 109.30(13) . . ? C34 C34A C312 110.12(14) . . ? C313 C34A C312 112.50(14) . . ? O35 C35 N36 120.54(16) . . ? O35 C35 C34A 123.17(15) . . ? N36 C35 C34A 116.25(14) . . ? C35 N36 C36A 124.85(15) . . ? C35 N36 H36 117.6 . . ? C36A N36 H36 117.6 . . ? C37 C36A C311 121.24(16) . . ? C37 C36A N36 119.70(16) . . ? C311 C36A N36 119.06(15) . . ? C36A C37 C38 119.28(18) . . ? C36A C37 H37 120.4 . . ? C38 C37 H37 120.4 . . ? C39 C38 C37 119.96(18) . . ? C39 C38 H38 120 . . ? C37 C38 H38 120 . . ? C38 C39 C310 120.38(18) . . ? C38 C39 H39 119.8 . . ? C310 C39 H39 119.8 . . ? C311 C310 C39 120.30(17) . . ? C311 C310 H310 119.8 . . ? C39 C310 H310 119.8 . . ? C310 C311 C36A 118.81(16) . . ? C310 C311 C312 123.14(16) . . ? C36A C311 C312 117.91(15) . . ? O312 C312 C311 112.23(14) . . ? O312 C312 C31 105.46(14) . . ? C311 C312 C31 108.63(14) . . ? O312 C312 C34A 111.83(14) . . ? C311 C312 C34A 109.59(14) . . ? C31 C312 C34A 108.94(13) . . ? C312 O312 H312 102.6(14) . . ? O313 C313 C34A 107.14(14) . . ? O313 C313 H31C 110.3 . . ? C34A C313 H31C 110.3 . . ? O313 C313 H31D 110.3 . . ? C34A C313 H31D 110.3 . . ? H31C C313 H31D 108.5 . . ? C313 O313 H313 113.6(18) . . ? 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 C112 C11 C12 N13 54.27(19) . . . . ? C11 C12 N13 C13 129.15(18) . . . . ? C11 C12 N13 C14 -55.06(19) . . . . ? C14 N13 C13 O13 2.7(3) . . . . ? C12 N13 C13 O13 178.33(17) . . . . ? C14 N13 C13 C131 -178.85(16) . . . . ? C12 N13 C13 C131 -3.2(3) . . . . ? O13 C13 C131 F133 -2.1(3) . . . . ? N13 C13 C131 F133 179.26(18) . . . . ? O13 C13 C131 F131 -123.03(18) . . . . ? N13 C13 C131 F131 58.4(2) . . . . ? O13 C13 C131 F132 116.9(2) . . . . ? N13 C13 C131 F132 -61.7(2) . . . . ? C13 N13 C14 C14A -126.97(16) . . . . ? C12 N13 C14 C14A 56.83(19) . . . . ? N13 C14 C14A C15 65.12(18) . . . . ? N13 C14 C14A C113 -176.08(13) . . . . ? N13 C14 C14A C112 -55.88(17) . . . . ? C14 C14A C15 O15 17.9(2) . . . . ? C113 C14A C15 O15 -101.52(18) . . . . ? C112 C14A C15 O15 139.53(16) . . . . ? C14 C14A C15 N16 -164.21(15) . . . . ? C113 C14A C15 N16 76.40(18) . . . . ? C112 C14A C15 N16 -42.55(19) . . . . ? O15 C15 N16 C16A -171.80(16) . . . . ? C14A C15 N16 C16A 10.3(2) . . . . ? C15 N16 C16A C111 11.3(3) . . . . ? C15 N16 C16A C17 -168.14(17) . . . . ? C111 C16A C17 C18 -0.3(3) . . . . ? N16 C16A C17 C18 179.18(16) . . . . ? C16A C17 C18 C19 -0.3(3) . . . . ? C17 C18 C19 C110 0.3(3) . . . . ? C18 C19 C110 C111 0.3(3) . . . . ? C19 C110 C111 C16A -0.8(2) . . . . ? C19 C110 C111 C112 177.60(16) . . . . ? C17 C16A C111 C110 0.8(3) . . . . ? N16 C16A C111 C110 -178.61(16) . . . . ? C17 C16A C111 C112 -177.66(16) . . . . ? N16 C16A C111 C112 2.9(2) . . . . ? C110 C111 C112 O112 28.4(2) . . . . ? C16A C111 C112 O112 -153.19(15) . . . . ? C110 C111 C112 C11 -94.18(18) . . . . ? C16A C111 C112 C11 84.28(18) . . . . ? C110 C111 C112 C14A 146.29(16) . . . . ? C16A C111 C112 C14A -35.3(2) . . . . ? C12 C11 C112 O112 63.60(18) . . . . ? C12 C11 C112 C111 -174.91(14) . . . . ? C12 C11 C112 C14A -54.95(18) . . . . ? C14 C14A C112 O112 -66.17(16) . . . . ? C15 C14A C112 O112 172.02(13) . . . . ? C113 C14A C112 O112 53.86(16) . . . . ? C14 C14A C112 C111 174.65(13) . . . . ? C15 C14A C112 C111 52.85(17) . . . . ? C113 C14A C112 C111 -65.31(16) . . . . ? C14 C14A C112 C11 54.69(17) . . . . ? C15 C14A C112 C11 -67.11(17) . . . . ? C113 C14A C112 C11 174.73(13) . . . . ? C14 C14A C113 O113 -54.50(17) . . . . ? C15 C14A C113 O113 65.83(17) . . . . ? C112 C14A C113 O113 -175.30(13) . . . . ? C212 C21 C22 N23 -56.00(18) . . . . ? C21 C22 N23 C23 -121.92(19) . . . . ? C21 C22 N23 C24 58.68(18) . . . . ? C24 N23 C23 O23 -3.3(3) . . . . ? C22 N23 C23 O23 177.32(17) . . . . ? C24 N23 C23 C231 175.55(15) . . . . ? C22 N23 C23 C231 -3.8(3) . . . . ? O23 C23 C231 F233 1.4(3) . . . . ? N23 C23 C231 F233 -177.55(17) . . . . ? O23 C23 C231 F232 -118.36(19) . . . . ? N23 C23 C231 F232 62.7(2) . . . . ? O23 C23 C231 F231 120.18(18) . . . . ? N23 C23 C231 F231 -58.8(2) . . . . ? C23 N23 C24 C24A 120.73(16) . . . . ? C22 N23 C24 C24A -59.82(18) . . . . ? N23 C24 C24A C213 179.80(13) . . . . ? N23 C24 C24A C25 -65.74(17) . . . . ? N23 C24 C24A C212 55.80(17) . . . . ? C24 C24A C25 O25 -28.1(2) . . . . ? C213 C24A C25 O25 88.98(19) . . . . ? C212 C24A C25 O25 -149.70(16) . . . . ? C24 C24A C25 N26 156.40(14) . . . . ? C213 C24A C25 N26 -86.55(18) . . . . ? C212 C24A C25 N26 34.8(2) . . . . ? O25 C25 N26 C26A -175.01(16) . . . . ? C24A C25 N26 C26A 0.5(2) . . . . ? C25 N26 C26A C27 161.81(17) . . . . ? C25 N26 C26A C211 -18.1(3) . . . . ? C211 C26A C27 C28 0.9(3) . . . . ? N26 C26A C27 C28 -178.93(17) . . . . ? C26A C27 C28 C29 0.1(3) . . . . ? C27 C28 C29 C210 -0.7(3) . . . . ? C28 C29 C210 C211 0.2(3) . . . . ? C29 C210 C211 C26A 0.8(3) . . . . ? C29 C210 C211 C212 -176.82(15) . . . . ? C27 C26A C211 C210 -1.4(3) . . . . ? N26 C26A C211 C210 178.46(16) . . . . ? C27 C26A C211 C212 176.37(15) . . . . ? N26 C26A C211 C212 -3.7(2) . . . . ? C210 C211 C212 O212 -21.5(2) . . . . ? C26A C211 C212 O212 160.81(14) . . . . ? C210 C211 C212 C21 95.12(19) . . . . ? C26A C211 C212 C21 -82.56(18) . . . . ? C210 C211 C212 C24A -144.28(17) . . . . ? C26A C211 C212 C24A 38.0(2) . . . . ? C22 C21 C212 O212 -65.14(16) . . . . ? C22 C21 C212 C211 174.55(14) . . . . ? C22 C21 C212 C24A 53.85(17) . . . . ? C24 C24A C212 O212 63.20(16) . . . . ? C213 C24A C212 O212 -58.61(17) . . . . ? C25 C24A C212 O212 -175.11(13) . . . . ? C24 C24A C212 C211 -173.57(13) . . . . ? C213 C24A C212 C211 64.62(17) . . . . ? C25 C24A C212 C211 -51.88(17) . . . . ? C24 C24A C212 C21 -52.50(17) . . . . ? C213 C24A C212 C21 -174.31(13) . . . . ? C25 C24A C212 C21 69.19(16) . . . . ? C24 C24A C213 O213 -63.44(17) . . . . ? C25 C24A C213 O213 178.61(13) . . . . ? C212 C24A C213 O213 59.06(18) . . . . ? C312 C31 C32 N33 53.78(19) . . . . ? C31 C32 N33 C33 131.49(18) . . . . ? C31 C32 N33 C34 -56.21(19) . . . . ? C34 N33 C33 O33 -9.1(3) . . . . ? C32 N33 C33 O33 162.85(17) . . . . ? C34 N33 C33 C331 166.25(16) . . . . ? C32 N33 C33 C331 -21.7(3) . . . . ? O33 C33 C331 F333 9.7(2) . . . . ? N33 C33 C331 F333 -166.08(17) . . . . ? O33 C33 C331 F332 128.26(18) . . . . ? N33 C33 C331 F332 -47.5(2) . . . . ? O33 C33 C331 F331 -110.54(19) . . . . ? N33 C33 C331 F331 73.7(2) . . . . ? C33 N33 C34 C34A -128.77(17) . . . . ? C32 N33 C34 C34A 58.32(19) . . . . ? N33 C34 C34A C35 62.98(18) . . . . ? N33 C34 C34A C313 178.71(14) . . . . ? N33 C34 C34A C312 -57.54(18) . . . . ? C34 C34A C35 O35 24.7(2) . . . . ? C313 C34A C35 O35 -92.78(19) . . . . ? C312 C34A C35 O35 145.74(16) . . . . ? C34 C34A C35 N36 -157.49(15) . . . . ? C313 C34A C35 N36 85.01(17) . . . . ? C312 C34A C35 N36 -36.5(2) . . . . ? O35 C35 N36 C36A 179.42(16) . . . . ? C34A C35 N36 C36A 1.6(2) . . . . ? C35 N36 C36A C37 -164.00(17) . . . . ? C35 N36 C36A C311 15.9(3) . . . . ? C311 C36A C37 C38 -0.5(3) . . . . ? N36 C36A C37 C38 179.43(18) . . . . ? C36A C37 C38 C39 -0.6(3) . . . . ? C37 C38 C39 C310 0.5(3) . . . . ? C38 C39 C310 C311 0.6(3) . . . . ? C39 C310 C311 C36A -1.6(3) . . . . ? C39 C310 C311 C312 174.03(17) . . . . ? C37 C36A C311 C310 1.6(3) . . . . ? N36 C36A C311 C310 -178.33(16) . . . . ? C37 C36A C311 C312 -174.31(16) . . . . ? N36 C36A C311 C312 5.8(2) . . . . ? C310 C311 C312 O312 19.2(2) . . . . ? C36A C311 C312 O312 -165.11(15) . . . . ? C310 C311 C312 C31 -97.00(19) . . . . ? C36A C311 C312 C31 78.69(19) . . . . ? C310 C311 C312 C34A 144.08(16) . . . . ? C36A C311 C312 C34A -40.2(2) . . . . ? C32 C31 C312 O312 65.54(17) . . . . ? C32 C31 C312 C311 -173.97(14) . . . . ? C32 C31 C312 C34A -54.65(19) . . . . ? C35 C34A C312 O312 178.98(13) . . . . ? C34 C34A C312 O312 -60.08(17) . . . . ? C313 C34A C312 O312 61.51(18) . . . . ? C35 C34A C312 C311 53.87(17) . . . . ? C34 C34A C312 C311 174.82(13) . . . . ? C313 C34A C312 C311 -63.59(18) . . . . ? C35 C34A C312 C31 -64.85(17) . . . . ? C34 C34A C312 C31 56.09(17) . . . . ? C313 C34A C312 C31 177.68(14) . . . . ? C35 C34A C313 O313 -176.31(13) . . . . ? C34 C34A C313 O313 65.42(17) . . . . ? C312 C34A C313 O313 -56.90(18) . . . . ? 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 N16 H16 O25 0.88 2.23 3.0866(19) 165.6 . O112 H112 O35 0.831(17) 1.928(19) 2.7143(18) 158(3) . O113 H113 O33 0.852(17) 1.944(17) 2.7936(18) 175(3) 4_556 N26 H26 O15 0.88 1.88 2.7539(18) 176.3 . O212 H212 O213 0.806(16) 1.891(19) 2.6071(18) 147(2) . O213 H213 O23 0.774(15) 2.247(18) 2.9006(18) 143(2) 4_466 O213 H213 O25 0.774(15) 2.252(19) 2.8046(18) 129.0(19) 4_466 N36 H36 O212 0.88 2.02 2.8621(19) 160.5 2_564 O312 H312 O313 0.826(15) 1.852(16) 2.606(2) 151(2) . O313 H313 O113 0.843(17) 1.956(18) 2.7902(19) 170(3) 4_556 #===END