#------------------------------------------------------------------------------ #$Date: 2014-03-11 06:56:53 +0000 (Tue, 11 Mar 2014) $ #$Revision: 104426 $ #$URL: svn://www.crystallography.net/cod/cif/7/11/20/7112070.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7112070 loop_ _publ_author_name 'Thomas J. Williams' 'Alan J. Reay' 'Adrian C. Whitwood' 'Ian J. S. Fairlamb' _publ_section_title ; A mild and selective Pd-mediated methodology for the synthesis of highly fluorescent 2-arylated tryptophans and tryptophan-containing peptides: a catalytic role for Pd0 nanoparticles? ; _journal_name_full Chem.Commun. _journal_page_first 3052 _journal_volume 50 _journal_year 2014 _chemical_absolute_configuration unk _chemical_formula_moiety 'C20 F N2 O3' _chemical_formula_sum 'C20 H19 F N2 O3' _chemical_formula_weight 354.37 _chemical_name_systematic ; ? ; _space_group_crystal_system trigonal _space_group_IT_number 146 _space_group_name_Hall 'R 3' _space_group_name_H-M_alt 'R 3' _symmetry_space_group_name_Hall 'R 3' _symmetry_space_group_name_H-M 'R 3 :H' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary iterative _atom_sites_solution_secondary difmap _audit_creation_date 2012-04-13 _audit_creation_method ; Olex2 1.1 (compiled 2011.11.01 svn.r2039, GUI svn.r3906) ; _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_formula_units_Z 9 _cell_length_a 21.0404(11) _cell_length_b 21.0404(11) _cell_length_c 10.4652(7) _cell_measurement_reflns_used 3569 _cell_measurement_temperature 110.00(10) _cell_measurement_theta_max 32.0836 _cell_measurement_theta_min 2.9596 _cell_volume 4012.2(4) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; Palatinus, L. & Chapuis, G. (2007). SUPERFLIP - a computer program for the solution of crystal structures by charge flipping in arbitrary dimensions. J. Appl. Cryst. 40, 786-790. ; _diffrn_ambient_temperature 110.00(10) _diffrn_detector_area_resol_mean 16.1450 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.920 _diffrn_measurement_details ; 1 omega -69.00 48.00 1.0000 12.8400 omega____ theta____ kappa____ phi______ frames - -25.1672 19.0000 -30.0000 117 2 omega -65.00 -35.00 1.0000 12.8400 omega____ theta____ kappa____ phi______ frames - -25.1672 -178.0000 -30.0000 30 3 omega 31.00 77.00 1.0000 12.8400 omega____ theta____ kappa____ phi______ frames - 26.4172 -128.0000 -7.0000 46 4 omega 39.00 100.00 1.0000 12.8400 omega____ theta____ kappa____ phi______ frames - 26.4172 -178.0000 -90.0000 61 5 omega 31.00 62.00 1.0000 12.8400 omega____ theta____ kappa____ phi______ frames - 26.4172 56.0000 117.0000 31 ; _diffrn_measurement_device_type 'SuperNova, Single source at offset), Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0179086000 _diffrn_orient_matrix_UB_12 -0.0357576000 _diffrn_orient_matrix_UB_13 0.0267633000 _diffrn_orient_matrix_UB_21 -0.0296459000 _diffrn_orient_matrix_UB_22 -0.0103234000 _diffrn_orient_matrix_UB_23 -0.0430230000 _diffrn_orient_matrix_UB_31 0.0175359000 _diffrn_orient_matrix_UB_32 -0.0111921000 _diffrn_orient_matrix_UB_33 -0.0453332000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_reflns_av_R_equivalents 0.0271 _diffrn_reflns_av_unetI/netI 0.0498 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 9531 _diffrn_reflns_theta_full 30.01 _diffrn_reflns_theta_max 32.16 _diffrn_reflns_theta_min 2.96 _diffrn_source 'SuperNova (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_T_max 0.990 _exptl_absorpt_correction_T_min 0.986 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_crystal_colour 'clear colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.320 _exptl_crystal_density_method 'not measured' _exptl_crystal_description irregular _exptl_crystal_F_000 1674 _exptl_crystal_size_max 0.2168 _exptl_crystal_size_mid 0.1531 _exptl_crystal_size_min 0.1393 _refine_diff_density_max 0.313 _refine_diff_density_min -0.229 _refine_diff_density_rms 0.045 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 245 _refine_ls_number_reflns 5613 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.036 _refine_ls_R_factor_all 0.0479 _refine_ls_R_factor_gt 0.0424 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0412P)^2^+1.5669P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0946 _refine_ls_wR_factor_ref 0.0995 _reflns_number_gt 5157 _reflns_number_total 5613 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file c3cc48481e2.cif _[local]_cod_data_source_block ijsf1202 _cod_original_cell_volume 4012.2(6) _cod_database_code 7112070 _chemical_oxdiff_formula 'C20 H19 F1 N2 O3' _chemical_oxdiff_usercomment 'Tom Williams TJW/5/173/465/1' _reflns_odcompleteness_completeness 99.89 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 30.01 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-y, x-y, z' 3 '-x+y, -x, z' 4 'x+2/3, y+1/3, z+1/3' 5 '-y+2/3, x-y+1/3, z+1/3' 6 '-x+y+2/3, -x+1/3, z+1/3' 7 'x+1/3, y+2/3, z+2/3' 8 '-y+1/3, x-y+2/3, z+2/3' 9 '-x+y+1/3, -x+2/3, z+2/3' 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 C1 C 0.54326(9) 0.29788(9) 0.51985(15) 0.0237(3) Uani 1 1 d . C2 C 0.52022(9) 0.34868(9) 0.52482(15) 0.0233(3) Uani 1 1 d . H2 H 0.5149 0.3667 0.6028 0.028 Uiso 1 1 calc R C3 C 0.50511(8) 0.37238(9) 0.41058(14) 0.0196(3) Uani 1 1 d . H3 H 0.4891 0.4063 0.4120 0.024 Uiso 1 1 calc R C4 C 0.51388(8) 0.34549(8) 0.29391(13) 0.0157(3) Uani 1 1 d . C5 C 0.53818(8) 0.29447(8) 0.29351(14) 0.0191(3) Uani 1 1 d . H5 H 0.5446 0.2767 0.2161 0.023 Uiso 1 1 calc R C6 C 0.55282(9) 0.27007(9) 0.40693(16) 0.0229(3) Uani 1 1 d . H6 H 0.5686 0.2359 0.4067 0.027 Uiso 1 1 calc R C7 C 0.49634(8) 0.36751(8) 0.17097(13) 0.0151(2) Uani 1 1 d . C8 C 0.51401(8) 0.43501(8) 0.12255(13) 0.0146(2) Uani 1 1 d . C9 C 0.55844(8) 0.50912(7) 0.18290(14) 0.0161(3) Uani 1 1 d . H9A H 0.5455 0.5056 0.2726 0.019 Uiso 1 1 calc R H9B H 0.5458 0.5429 0.1428 0.019 Uiso 1 1 calc R C10 C 0.64169(7) 0.54050(8) 0.17169(13) 0.0139(2) Uani 1 1 d . H10 H 0.6561 0.5114 0.2248 0.017 Uiso 1 1 calc R C11 C 0.66116(8) 0.53645(8) 0.03302(13) 0.0153(3) Uani 1 1 d . C12 C 0.68382(11) 0.46603(11) -0.11590(16) 0.0309(4) Uani 1 1 d . H12A H 0.6398 0.4503 -0.1647 0.046 Uiso 1 1 calc R H12B H 0.6970 0.4285 -0.1176 0.046 Uiso 1 1 calc R H12C H 0.7228 0.5103 -0.1522 0.046 Uiso 1 1 calc R C13 C 0.75258(8) 0.65834(8) 0.20747(13) 0.0162(3) Uani 1 1 d . C14 C 0.78405(9) 0.73524(9) 0.25806(17) 0.0258(3) Uani 1 1 d . H14A H 0.8185 0.7433 0.3250 0.039 Uiso 1 1 calc R H14B H 0.7452 0.7418 0.2912 0.039 Uiso 1 1 calc R H14C H 0.8086 0.7697 0.1902 0.039 Uiso 1 1 calc R C15 C 0.48395(8) 0.42278(8) -0.00434(13) 0.0154(3) Uani 1 1 d . C16 C 0.48216(8) 0.46893(8) -0.09995(15) 0.0187(3) Uani 1 1 d . H16 H 0.5061 0.5195 -0.0880 0.022 Uiso 1 1 calc R C17 C 0.44428(9) 0.43801(9) -0.21186(15) 0.0219(3) Uani 1 1 d . H17 H 0.4429 0.4682 -0.2754 0.026 Uiso 1 1 calc R C18 C 0.40778(9) 0.36167(9) -0.23109(15) 0.0220(3) Uani 1 1 d . H18 H 0.3818 0.3421 -0.3064 0.026 Uiso 1 1 calc R C19 C 0.40995(8) 0.31516(9) -0.13967(15) 0.0211(3) Uani 1 1 d . H19 H 0.3867 0.2648 -0.1531 0.025 Uiso 1 1 calc R C20 C 0.44815(8) 0.34650(8) -0.02694(14) 0.0165(3) Uani 1 1 d . F1 F 0.55774(7) 0.27429(7) 0.63125(9) 0.0371(3) Uani 1 1 d . N1 N 0.67922(7) 0.61582(7) 0.21652(12) 0.0174(2) Uani 1 1 d . H1 H 0.6540(13) 0.6359(13) 0.241(2) 0.039(6) Uiso 1 1 d . N2 N 0.45744(7) 0.31386(7) 0.08007(12) 0.0179(2) Uani 1 1 d . H2A H 0.4351(13) 0.2686(14) 0.093(2) 0.036(6) Uiso 1 1 d . O1 O 0.66376(6) 0.57685(6) -0.05103(10) 0.0198(2) Uani 1 1 d . O2 O 0.67144(6) 0.47957(6) 0.01536(10) 0.0205(2) Uani 1 1 d . O3 O 0.79097(6) 0.63528(6) 0.16024(10) 0.0196(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 0.0238(8) 0.0237(8) 0.0176(6) 0.0079(6) 0.0016(6) 0.0075(6) C2 0.0235(8) 0.0262(8) 0.0161(6) 0.0013(6) 0.0049(6) 0.0095(6) C3 0.0186(7) 0.0193(7) 0.0205(6) 0.0010(5) 0.0040(5) 0.0092(6) C4 0.0140(6) 0.0127(6) 0.0171(6) 0.0018(5) 0.0007(5) 0.0042(5) C5 0.0216(7) 0.0163(6) 0.0174(6) -0.0010(5) -0.0006(5) 0.0079(6) C6 0.0261(8) 0.0184(7) 0.0249(7) 0.0035(6) -0.0013(6) 0.0117(6) C7 0.0134(6) 0.0151(6) 0.0151(6) -0.0008(5) 0.0007(5) 0.0058(5) C8 0.0129(6) 0.0143(6) 0.0159(6) -0.0011(5) 0.0006(5) 0.0063(5) C9 0.0151(6) 0.0130(6) 0.0190(6) -0.0014(5) 0.0014(5) 0.0060(5) C10 0.0138(6) 0.0130(6) 0.0157(6) -0.0014(5) 0.0003(5) 0.0073(5) C11 0.0135(6) 0.0134(6) 0.0167(6) -0.0021(5) 0.0000(5) 0.0050(5) C12 0.0442(11) 0.0346(9) 0.0200(7) -0.0044(7) 0.0067(7) 0.0243(9) C13 0.0149(6) 0.0161(6) 0.0171(6) -0.0005(5) -0.0003(5) 0.0074(5) C14 0.0184(7) 0.0182(7) 0.0362(9) -0.0081(6) -0.0005(6) 0.0057(6) C15 0.0137(6) 0.0156(6) 0.0163(6) -0.0003(5) 0.0012(5) 0.0067(5) C16 0.0166(6) 0.0167(6) 0.0229(7) 0.0021(5) 0.0011(5) 0.0084(6) C17 0.0194(7) 0.0268(8) 0.0200(7) 0.0056(6) 0.0005(6) 0.0119(6) C18 0.0182(7) 0.0280(8) 0.0178(7) -0.0021(6) -0.0029(5) 0.0101(6) C19 0.0192(7) 0.0194(7) 0.0218(7) -0.0029(6) -0.0033(6) 0.0074(6) C20 0.0151(6) 0.0152(6) 0.0183(6) -0.0005(5) -0.0003(5) 0.0068(5) F1 0.0498(7) 0.0456(7) 0.0197(5) 0.0118(5) 0.0005(5) 0.0268(6) N1 0.0136(5) 0.0147(6) 0.0236(6) -0.0054(5) 0.0011(5) 0.0068(5) N2 0.0187(6) 0.0121(6) 0.0193(6) -0.0016(5) -0.0032(5) 0.0050(5) O1 0.0206(5) 0.0171(5) 0.0196(5) 0.0029(4) 0.0010(4) 0.0079(4) O2 0.0281(6) 0.0215(5) 0.0168(5) -0.0020(4) 0.0027(4) 0.0160(5) O3 0.0161(5) 0.0202(5) 0.0240(5) -0.0031(4) 0.0006(4) 0.0101(4) 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' F F 0.0171 0.0103 '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' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z -2 1 0 0.0998 -2.0000 0.9990 -0.0002 0.0001 0.0490 -0.0462 2 -1 0 0.1128 2.0000 -0.9990 0.0002 -0.0001 -0.0490 0.0462 0 0 1 0.0890 -0.0001 -0.0002 0.9992 0.0267 -0.0430 -0.0453 0 0 -1 0.0736 0.0001 0.0002 -0.9992 -0.0267 0.0430 0.0453 1 -1 -1 0.0662 0.9999 -0.9990 -0.9991 -0.0089 0.0237 0.0740 -1 1 1 0.0732 -0.9999 0.9990 0.9991 0.0089 -0.0237 -0.0740 -1 0 -1 0.0746 -1.0001 -0.0000 -0.9993 -0.0088 0.0726 0.0278 1 0 1 0.0746 1.0001 0.0000 0.9993 0.0088 -0.0726 -0.0278 1 -2 0 0.0574 0.9996 -1.9986 -0.0001 0.0536 -0.0090 0.0399 -1 2 0 0.0854 -0.9996 1.9986 0.0001 -0.0536 0.0090 -0.0399 -1 -1 0 0.0706 -1.0004 -0.9996 -0.0002 0.0537 0.0400 -0.0063 1 1 0 0.0826 1.0004 0.9996 0.0002 -0.0537 -0.0400 0.0063 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C6 C1 C2 123.01(14) F1 C1 C2 118.73(15) F1 C1 C6 118.26(15) C1 C2 H2 120.7 C1 C2 C3 118.53(14) C3 C2 H2 120.7 C2 C3 H3 119.8 C2 C3 C4 120.38(15) C4 C3 H3 119.8 C3 C4 C5 119.07(13) C3 C4 C7 122.07(13) C5 C4 C7 118.84(13) C4 C5 H5 119.5 C6 C5 C4 120.97(14) C6 C5 H5 119.5 C1 C6 C5 118.04(15) C1 C6 H6 121.0 C5 C6 H6 121.0 C8 C7 C4 131.75(13) C8 C7 N2 109.46(12) N2 C7 C4 118.73(13) C7 C8 C9 128.77(13) C7 C8 C15 106.77(12) C15 C8 C9 124.41(13) C8 C9 H9A 108.9 C8 C9 H9B 108.9 C8 C9 C10 113.51(11) H9A C9 H9B 107.7 C10 C9 H9A 108.9 C10 C9 H9B 108.9 C9 C10 H10 109.3 C11 C10 C9 109.25(11) C11 C10 H10 109.3 N1 C10 C9 109.00(11) N1 C10 H10 109.3 N1 C10 C11 110.79(11) O1 C11 C10 125.11(13) O1 C11 O2 124.20(13) O2 C11 C10 110.62(12) H12A C12 H12B 109.5 H12A C12 H12C 109.5 H12B C12 H12C 109.5 O2 C12 H12A 109.5 O2 C12 H12B 109.5 O2 C12 H12C 109.5 N1 C13 C14 115.58(13) O3 C13 C14 122.74(13) O3 C13 N1 121.68(13) C13 C14 H14A 109.5 C13 C14 H14B 109.5 C13 C14 H14C 109.5 H14A C14 H14B 109.5 H14A C14 H14C 109.5 H14B C14 H14C 109.5 C16 C15 C8 133.95(14) C16 C15 C20 118.84(13) C20 C15 C8 107.18(12) C15 C16 H16 120.5 C17 C16 C15 119.03(14) C17 C16 H16 120.5 C16 C17 H17 119.5 C16 C17 C18 121.06(15) C18 C17 H17 119.5 C17 C18 H18 119.5 C19 C18 C17 121.06(14) C19 C18 H18 119.5 C18 C19 H19 121.1 C18 C19 C20 117.72(14) C20 C19 H19 121.1 C19 C20 C15 122.26(13) N2 C20 C15 107.62(12) N2 C20 C19 130.10(13) C10 N1 H1 119.8(16) C13 N1 C10 121.37(12) C13 N1 H1 118.4(16) C7 N2 H2A 125.4(15) C20 N2 C7 108.94(12) C20 N2 H2A 124.3(15) C11 O2 C12 115.68(12) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 C2 1.378(3) C1 C6 1.377(2) C1 F1 1.3600(18) C2 H2 0.9300 C2 C3 1.392(2) C3 H3 0.9300 C3 C4 1.396(2) C4 C5 1.401(2) C4 C7 1.4755(19) C5 H5 0.9300 C5 C6 1.388(2) C6 H6 0.9300 C7 C8 1.373(2) C7 N2 1.3876(18) C8 C9 1.4989(19) C8 C15 1.4377(19) C9 H9A 0.9700 C9 H9B 0.9700 C9 C10 1.5366(19) C10 H10 0.9800 C10 C11 1.5218(19) C10 N1 1.4503(18) C11 O1 1.2052(18) C11 O2 1.3312(18) C12 H12A 0.9600 C12 H12B 0.9600 C12 H12C 0.9600 C12 O2 1.4526(19) C13 C14 1.505(2) C13 N1 1.3458(19) C13 O3 1.2345(17) C14 H14A 0.9600 C14 H14B 0.9600 C14 H14C 0.9600 C15 C16 1.408(2) C15 C20 1.411(2) C16 H16 0.9300 C16 C17 1.383(2) C17 H17 0.9300 C17 C18 1.406(2) C18 H18 0.9300 C18 C19 1.386(2) C19 H19 0.9300 C19 C20 1.394(2) C20 N2 1.3778(19) N1 H1 0.87(2) N2 H2A 0.84(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 N1 H1 O1 0.87(2) 2.06(2) 2.9155(16) 170(2) 6_565 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 C1 C2 C3 C4 -0.6(2) C2 C1 C6 C5 -0.2(2) C2 C3 C4 C5 -0.1(2) C2 C3 C4 C7 178.13(14) C3 C4 C5 C6 0.6(2) C3 C4 C7 C8 47.4(2) C3 C4 C7 N2 -135.53(15) C4 C5 C6 C1 -0.5(2) C4 C7 C8 C9 0.3(3) C4 C7 C8 C15 177.89(14) C4 C7 N2 C20 -179.18(13) C5 C4 C7 C8 -134.34(16) C5 C4 C7 N2 42.70(19) C6 C1 C2 C3 0.7(2) C7 C4 C5 C6 -177.66(14) C7 C8 C9 C10 80.64(18) C7 C8 C15 C16 178.36(15) C7 C8 C15 C20 0.43(16) C8 C7 N2 C20 -1.52(16) C8 C9 C10 C11 50.88(16) C8 C9 C10 N1 172.07(11) C8 C15 C16 C17 -176.53(15) C8 C15 C20 C19 177.08(14) C8 C15 C20 N2 -1.35(16) C9 C8 C15 C16 -4.0(2) C9 C8 C15 C20 178.12(13) C9 C10 C11 O1 75.70(17) C9 C10 C11 O2 -101.15(13) C9 C10 N1 C13 -174.53(13) C10 C11 O2 C12 174.64(13) C11 C10 N1 C13 -54.29(17) C14 C13 N1 C10 -179.88(13) C15 C8 C9 C10 -96.52(16) C15 C16 C17 C18 0.1(2) C15 C20 N2 C7 1.77(16) C16 C15 C20 C19 -1.2(2) C16 C15 C20 N2 -179.65(13) C16 C17 C18 C19 -1.4(2) C17 C18 C19 C20 1.4(2) C18 C19 C20 C15 -0.1(2) C18 C19 C20 N2 177.96(15) C19 C20 N2 C7 -176.50(15) C20 C15 C16 C17 1.2(2) F1 C1 C2 C3 -179.67(14) F1 C1 C6 C5 -179.82(14) N1 C10 C11 O1 -44.40(19) N1 C10 C11 O2 138.75(12) N2 C7 C8 C9 -176.90(13) N2 C7 C8 C15 0.65(16) O1 C11 O2 C12 -2.2(2) O3 C13 N1 C10 0.3(2)