#------------------------------------------------------------------------------ #$Date: 2017-12-21 11:29:59 +0200 (Thu, 21 Dec 2017) $ #$Revision: 204446 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/54/85/1548527.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_1548527 loop_ _publ_author_name 'Brendan T. Parr' 'Christos Economou' 'Seth B. Herzon' _publ_section_title ; A concise synthesis of (+)-batzelladine B from simple pyrrole-based starting materials ; _journal_name_full Nature _journal_page_first 507 _journal_page_last 510 _journal_paper_doi 10.1038/nature14902 _journal_volume 525 _journal_year 2015 _chemical_formula_sum 'C19 H22 F3 N3 O7' _chemical_formula_weight 461.39 _space_group_IT_number 4 _symmetry_cell_setting monoclinic _symmetry_Int_Tables_number 4 _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _cell_angle_alpha 90. _cell_angle_beta 99.289(7) _cell_angle_gamma 90. _cell_formula_units_Z 2 _cell_length_a 9.4094(3) _cell_length_b 11.7301(3) _cell_length_c 9.5007(6) _cell_volume 1034.87(8) _diffrn_ambient_temperature 93 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71075 _exptl_absorpt_coefficient_mu 0.130 _exptl_crystal_density_diffrn 1.481 _exptl_crystal_F_000 480 _refine_ls_goodness_of_fit_ref 1.162 _refine_ls_number_parameters 303 _refine_ls_number_reflns 3647 _refine_ls_R_factor_all 0.0573 _refine_ls_R_factor_gt 0.0510 _refine_ls_wR_factor_gt 0.0721 _refine_ls_wR_factor_ref 0.0736 _cod_data_source_file Nature-2015-525-507.cif _cod_data_source_block spider-15033 _cod_depositor_comments ; Crystal size 0.200 x 0.190 x 0.180 mm3 Crystal color and habit Colorless Block Diffractometer Rigaku R-AXIS RAPID imaging plate T range for data collection 3.318 to 25.010 Index ranges -11 = h = 11, -13 = k = 13, -11 = l = 11 Reflections collected 33505 Independent reflections 3647 [R(int) = 0.0830] Observed reflections (I > 2s(I)) 3299 Completeness to ? = 25.010 99.7 % Absorption correction Semi-empirical from equivalents Max. and min. transmission 0.977 and 0.873 Solution method SHELXT-2014/5 (Sheldrick, 2014) Refinement method SHELXL-2014/7 (Sheldrick, 2014) Data / restraints / parameters 3647 / 1 / 303 Goodness-of-fit on F2 1.162 Final R indices [I>2s(I)] R1 = 0.0510, wR2 = 0.0721 R indices (all data) R1 = 0.0573, wR2 = 0.0736 Absolute structure parameter -0.1(4) Largest diff. peak and hole 0.211 and -0.178 e.A-3 ; _cod_original_sg_symbol_H-M 'P 21' _cod_database_code 1548527 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 x,y,z 2 -x,1/2+y,-z 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 0.028(2) 0.028(2) 0.030(2) 0.0050(10) 0.0040(10) -0.0010(10) O2 0.027(2) 0.042(2) 0.042(2) -0.019(2) 0.002(2) 0.000(2) O3 0.0180(10) 0.023(2) 0.028(2) -0.0010(10) 0.0020(10) -0.0010(10) O4 0.038(2) 0.029(2) 0.044(2) 0.001(2) 0.009(2) -0.011(2) O5 0.024(2) 0.041(2) 0.043(2) -0.009(2) 0.0020(10) 0.000(2) N1 0.021(2) 0.023(2) 0.031(2) 0.004(2) -0.003(2) 0.000(2) F1 0.046(2) 0.0260(10) 0.086(2) 0.006(2) -0.020(2) -0.0120(10) F2 0.040(2) 0.072(2) 0.027(2) -0.0060(10) -0.0010(10) 0.008(2) N2 0.026(2) 0.025(2) 0.028(2) 0.004(2) -0.003(2) -0.001(2) F3 0.0270(10) 0.034(2) 0.049(2) -0.0110(10) 0.0000(10) 0.0020(10) N3 0.022(2) 0.024(2) 0.025(2) 0.000(2) 0.004(2) 0.003(2) C1 0.022(2) 0.030(3) 0.020(2) 0.006(2) 0.001(2) 0.000(2) C2 0.030(2) 0.025(2) 0.029(3) -0.003(2) 0.004(2) -0.003(2) C3 0.027(2) 0.023(2) 0.027(2) -0.003(2) 0.007(2) -0.001(2) C4 0.022(2) 0.023(3) 0.027(2) -0.003(2) 0.003(2) -0.003(2) C5 0.024(2) 0.029(2) 0.021(2) 0.003(2) 0.005(2) 0.003(2) C6 0.026(2) 0.024(2) 0.031(2) 0.007(2) 0.004(2) 0.002(2) O6 0.032(2) 0.026(2) 0.045(2) -0.001(2) -0.005(2) 0.0040(10) C7 0.028(2) 0.026(2) 0.036(3) 0.002(2) 0.001(2) -0.002(2) O7 0.030(2) 0.026(2) 0.030(2) 0.0000(10) -0.0030(10) -0.0030(10) C8 0.022(2) 0.029(3) 0.028(3) -0.003(2) 0.000(2) 0.000(2) C9 0.027(2) 0.028(2) 0.022(2) -0.003(2) 0.002(2) 0.001(2) C10 0.016(2) 0.029(2) 0.023(2) 0.000(2) 0.002(2) -0.004(2) C11 0.026(2) 0.026(2) 0.026(2) 0.000(2) 0.009(2) -0.001(2) C12 0.026(2) 0.025(2) 0.022(2) -0.001(2) 0.006(2) 0.000(2) C13 0.027(3) 0.036(3) 0.028(3) -0.005(2) 0.012(2) -0.004(2) C14 0.032(3) 0.033(3) 0.042(3) -0.008(2) 0.001(2) 0.010(2) C15 0.026(2) 0.030(2) 0.024(2) 0.000(2) 0.002(2) 0.005(2) C16 0.044(3) 0.025(2) 0.035(3) -0.001(2) 0.009(2) 0.003(2) C17 0.044(3) 0.032(3) 0.027(3) 0.008(2) 0.006(2) 0.010(2) C18 0.026(2) 0.027(3) 0.022(2) 0.002(2) 0.006(2) 0.000(2) C19 0.032(2) 0.019(2) 0.035(3) -0.001(2) 0.006(2) 0.000(2) loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O Uani 0.5001(3) 0.5444(2) 0.0573(3) 1.000 0.0287(12) . . . . O2 O Uani 0.3718(3) 0.6281(3) 0.3957(3) 1.000 0.0374(12) . . . . O3 O Uani 0.2665(3) 0.5138(2) 0.2182(3) 1.000 0.0232(10) . . . . O4 O Uani 0.0279(3) 0.3698(3) 0.2070(3) 1.000 0.0367(12) . . . . O5 O Uani -0.1060(3) 0.5193(3) 0.1203(3) 1.000 0.0364(12) . . . . N1 N Uani 0.8641(4) 0.2256(3) 0.3983(4) 1.000 0.0258(12) . . . . F1 F Uani 0.3692(3) 0.5060(2) 0.7176(3) 1.000 0.0561(10) . . . . F2 F Uani 0.2825(3) 0.3895(3) 0.8560(3) 1.000 0.0470(12) . . . . N2 N Uani 0.8207(4) 0.4077(3) 0.4699(4) 1.000 0.0272(12) . . . . F3 F Uani 0.4129(2) 0.3280(2) 0.7076(3) 1.000 0.0373(10) . . . . N3 N Uani 0.6340(3) 0.3013(3) 0.3451(4) 1.000 0.0236(12) . . . . C1 C Uani 0.7730(4) 0.3109(4) 0.4036(4) 1.000 0.0243(14) . . . . C2 C Uani 0.7678(5) 0.5192(4) 0.4369(4) 1.000 0.0281(14) . . . . C3 C Uani 0.6451(4) 0.5546(4) 0.3652(4) 1.000 0.0254(12) . . . . C4 C Uani 0.5152(4) 0.4846(3) 0.3004(4) 1.000 0.0241(14) . . . . C5 C Uani 0.5180(4) 0.3709(3) 0.3848(4) 1.000 0.0245(12) . . . . C6 C Uani 0.3905(4) 0.2901(4) 0.3443(5) 1.000 0.0271(12) . . . . O6 O Uani 0.1034(3) 0.4789(2) 0.5821(3) 1.000 0.0356(12) . . . . C7 C Uani 0.4204(5) 0.2310(4) 0.2069(5) 1.000 0.0305(14) . . . . O7 O Uani 0.1375(3) 0.2891(2) 0.5792(3) 1.000 0.0295(12) . . . . C8 C Uani 0.5795(4) 0.2564(4) 0.1992(4) 1.000 0.0268(16) . . . . C9 C Uani 0.5954(4) 0.3557(3) 0.0984(4) 1.000 0.0259(12) . . . . C10 C Uani 0.5303(4) 0.4665(4) 0.1403(4) 1.000 0.0228(12) . . . . C11 C Uani 0.3798(4) 0.5525(4) 0.3111(4) 1.000 0.0255(12) . . . . C12 C Uani 0.1286(4) 0.5627(3) 0.2253(4) 1.000 0.0241(12) . . . . C13 C Uani 0.0169(5) 0.4707(4) 0.1866(4) 1.000 0.0295(17) . . . . C14 C Uani -0.0834(5) 0.6417(4) 0.1074(5) 1.000 0.0362(17) . . . . C15 C Uani 0.0800(4) 0.6558(4) 0.1161(4) 1.000 0.0269(12) . . . . C16 C Uani 0.1297(5) 0.7758(4) 0.1643(5) 1.000 0.0344(16) . . . . C17 C Uani 0.1250(5) 0.6266(4) -0.0285(4) 1.000 0.0343(17) . . . . C18 C Uani 0.1703(4) 0.3886(4) 0.6151(4) 1.000 0.0248(14) . . . . C19 C Uani 0.3097(4) 0.4032(4) 0.7229(4) 1.000 0.0286(14) . . . . H1A H Uiso 0.828(5) 0.152(4) 0.381(5) 1.000 0.041(14) . . . . H1B H Uiso 0.954(5) 0.240(4) 0.436(5) 1.000 0.044(15) . . . . H2 H Uiso 0.918(5) 0.407(5) 0.516(5) 1.000 0.053(15) . . . . H2A H Uiso 0.83230 0.57850 0.47300 1.000 0.0340 . . . . H3 H Uiso 0.63630 0.63470 0.35190 1.000 0.0310 . . . . H5 H Uiso 0.53480 0.38580 0.48980 1.000 0.0300 . . . . H6A H Uiso 0.29860 0.33290 0.32640 1.000 0.0330 . . . . H6B H Uiso 0.38580 0.23360 0.42080 1.000 0.0330 . . . . H7A H Uiso 0.40400 0.14780 0.21160 1.000 0.0360 . . . . H7B H Uiso 0.35710 0.26210 0.12230 1.000 0.0360 . . . . H8 H Uiso 0.63300 0.18690 0.17620 1.000 0.0320 . . . . H9A H Uiso 0.69900 0.36810 0.09590 1.000 0.0310 . . . . H9B H Uiso 0.54880 0.33470 0.00090 1.000 0.0310 . . . . H12 H Uiso 0.12540 0.59150 0.32380 1.000 0.0290 . . . . H14A H Uiso -0.11800 0.68350 0.18590 1.000 0.0430 . . . . H14B H Uiso -0.13500 0.67060 0.01520 1.000 0.0430 . . . . H16A H Uiso 0.09830 0.79310 0.25540 1.000 0.0520 . . . . H16B H Uiso 0.08760 0.83140 0.09240 1.000 0.0520 . . . . H16C H Uiso 0.23490 0.77990 0.17590 1.000 0.0520 . . . . H17A H Uiso 0.23030 0.62270 -0.01740 1.000 0.0510 . . . . H17B H Uiso 0.08950 0.68570 -0.09830 1.000 0.0510 . . . . H17C H Uiso 0.08390 0.55270 -0.06180 1.000 0.0510 . . . . 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 O3 C12 117.5(3) . . . yes C13 O5 C14 109.2(3) . . . yes C1 N2 C2 126.8(4) . . . yes C1 N3 C5 124.5(4) . . . yes C1 N3 C8 125.5(3) . . . yes C5 N3 C8 106.1(3) . . . yes N1 C1 N2 119.2(4) . . . yes N1 C1 N3 121.0(4) . . . yes N2 C1 N3 119.8(4) . . . yes H1A N1 H1B 123(4) . . . no C1 N1 H1A 119(3) . . . no C1 N1 H1B 115(3) . . . no C1 N2 H2 116(3) . . . no N2 C2 C3 131.0(4) . . . yes C2 N2 H2 113(4) . . . no C2 C3 C4 128.6(4) . . . no C3 C4 C10 105.9(3) . . . no C3 C4 C11 108.6(3) . . . no C3 C4 C5 108.0(3) . . . no C10 C4 C11 110.2(3) . . . no C5 C4 C10 112.9(3) . . . no C5 C4 C11 111.1(3) . . . no C4 C5 C6 117.1(3) . . . no N3 C5 C6 100.2(3) . . . yes N3 C5 C4 107.3(3) . . . yes C5 C6 C7 104.4(3) . . . no C6 C7 C8 105.4(3) . . . no N3 C8 C7 102.4(3) . . . yes C7 C8 C9 111.8(3) . . . no N3 C8 C9 105.0(3) . . . yes C8 C9 C10 113.8(3) . . . no C4 C10 C9 118.4(3) . . . no O1 C10 C4 118.8(4) . . . yes O1 C10 C9 122.6(3) . . . yes O2 C11 O3 123.7(4) . . . yes O2 C11 C4 124.9(3) . . . yes O3 C11 C4 111.3(3) . . . yes O3 C12 C13 107.6(3) . . . yes C13 C12 C15 103.0(3) . . . no O3 C12 C15 115.5(3) . . . yes O4 C13 C12 128.8(4) . . . yes O5 C13 C12 108.8(4) . . . yes O4 C13 O5 122.4(4) . . . yes O5 C14 C15 105.1(4) . . . yes C14 C15 C17 110.2(3) . . . no C16 C15 C17 110.9(4) . . . no C12 C15 C14 98.5(3) . . . no C12 C15 C16 114.3(3) . . . no C12 C15 C17 110.6(3) . . . no C14 C15 C16 111.7(4) . . . no N2 C2 H2A 115.00 . . . no C3 C2 H2A 114.00 . . . no C2 C3 H3 116.00 . . . no C4 C3 H3 116.00 . . . no N3 C5 H5 111.00 . . . no C4 C5 H5 111.00 . . . no C6 C5 H5 111.00 . . . no C5 C6 H6A 111.00 . . . no C5 C6 H6B 111.00 . . . no C7 C6 H6A 111.00 . . . no C7 C6 H6B 111.00 . . . no H6A C6 H6B 109.00 . . . no C6 C7 H7A 111.00 . . . no C6 C7 H7B 111.00 . . . no C8 C7 H7A 111.00 . . . no C8 C7 H7B 111.00 . . . no H7A C7 H7B 109.00 . . . no N3 C8 H8 112.00 . . . no C7 C8 H8 112.00 . . . no C9 C8 H8 112.00 . . . no C8 C9 H9A 109.00 . . . no C8 C9 H9B 109.00 . . . no C10 C9 H9A 109.00 . . . no C10 C9 H9B 109.00 . . . no H9A C9 H9B 108.00 . . . no O3 C12 H12 110.00 . . . no C13 C12 H12 110.00 . . . no C15 C12 H12 110.00 . . . no O5 C14 H14A 111.00 . . . no O5 C14 H14B 111.00 . . . no C15 C14 H14A 111.00 . . . no C15 C14 H14B 111.00 . . . no H14A C14 H14B 109.00 . . . no C15 C16 H16A 109.00 . . . no C15 C16 H16B 110.00 . . . no C15 C16 H16C 109.00 . . . no H16A C16 H16B 109.00 . . . no H16A C16 H16C 110.00 . . . no H16B C16 H16C 109.00 . . . no C15 C17 H17A 109.00 . . . no C15 C17 H17B 109.00 . . . no C15 C17 H17C 109.00 . . . no H17A C17 H17B 110.00 . . . no H17A C17 H17C 109.00 . . . no H17B C17 H17C 109.00 . . . no O6 C18 O7 129.6(4) . . . yes O6 C18 C19 114.5(4) . . . yes O7 C18 C19 115.8(4) . . . yes F1 C19 F2 106.8(3) . . . yes F1 C19 F3 106.0(3) . . . yes F1 C19 C18 113.2(4) . . . yes F2 C19 F3 106.0(3) . . . yes F2 C19 C18 110.1(3) . . . yes F3 C19 C18 114.2(3) . . . yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C10 1.211(5) . . yes O2 C11 1.207(5) . . yes O3 C11 1.348(5) . . yes O3 C12 1.430(5) . . yes O4 C13 1.201(6) . . yes O5 C13 1.351(5) . . yes O5 C14 1.460(6) . . yes N1 C1 1.324(6) . . yes F1 C19 1.334(5) . . yes N2 C1 1.340(6) . . yes F2 C19 1.340(5) . . yes N2 C2 1.416(6) . . yes N3 C5 1.461(5) . . yes N3 C1 1.341(5) . . yes F3 C19 1.337(5) . . yes N3 C8 1.494(5) . . yes N1 H1B 0.88(5) . . no N1 H1A 0.93(5) . . no N2 H2 0.95(5) . . no C2 C3 1.310(6) . . no C3 C4 1.518(6) . . no C4 C11 1.520(6) . . no C4 C5 1.554(5) . . no C4 C10 1.565(5) . . no C5 C6 1.529(6) . . no O6 C18 1.246(5) . . yes C6 C7 1.544(7) . . no O7 C18 1.241(5) . . yes C7 C8 1.540(6) . . no C8 C9 1.531(6) . . no C9 C10 1.517(6) . . no C12 C13 1.510(6) . . no C12 C15 1.525(6) . . no C14 C15 1.535(6) . . no C15 C17 1.540(6) . . no C15 C16 1.530(7) . . no C2 H2A 0.9500 . . no C3 H3 0.9500 . . no C5 H5 1.0000 . . no C6 H6A 0.9900 . . no C6 H6B 0.9900 . . no C7 H7A 0.9900 . . no C7 H7B 0.9900 . . no C8 H8 1.0000 . . no C9 H9A 0.9900 . . no C9 H9B 0.9900 . . no C12 H12 1.0000 . . no C14 H14A 0.9900 . . no C14 H14B 0.9900 . . no C16 H16A 0.9800 . . no C16 H16B 0.9800 . . no C16 H16C 0.9800 . . no C17 H17B 0.9800 . . no C17 H17C 0.9800 . . no C17 H17A 0.9800 . . no C18 C19 1.538(5) . . no 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 _geom_hbond_publ_flag N1 H1A O6 0.93(5) 2.14(5) 2.913(4) 139(4) 2_646 yes N1 H1B O7 0.88(5) 2.10(5) 2.949(5) 162(4) 1_655 yes N2 H2 O6 0.95(5) 1.95(5) 2.827(5) 153(5) 1_655 yes N2 H2 O7 0.95(5) 2.48(5) 3.302(5) 145(5) 1_655 yes C2 H2A O7 0.9500 2.5400 3.299(5) 136.00 2_656 yes C3 H3 F3 0.9500 2.3600 3.308(5) 172.00 2_656 yes C6 H6A O3 0.9900 2.3600 3.038(5) 125.00 . yes C8 H8 F1 1.0000 2.3500 3.060(5) 127.00 2_646 yes C9 H9A O5 0.9900 2.5400 3.381(5) 143.00 1_655 yes C14 H14A O7 0.9900 2.5800 3.550(5) 165.00 2_556 yes C17 H17B O4 0.9800 2.5700 3.507(6) 161.00 2_555 yes 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 C12 O3 C11 O2 -2.6(6) . . . . no C12 O3 C11 C4 174.4(3) . . . . no C11 O3 C12 C13 -146.6(3) . . . . no C11 O3 C12 C15 98.9(4) . . . . no C14 O5 C13 O4 -178.0(4) . . . . no C14 O5 C13 C12 1.6(4) . . . . no C13 O5 C14 C15 23.0(4) . . . . no C2 N2 C1 N1 149.7(4) . . . . no C2 N2 C1 N3 -31.0(6) . . . . no C1 N2 C2 C3 19.4(7) . . . . no C5 N3 C1 N1 158.2(4) . . . . no C5 N3 C1 N2 -21.0(6) . . . . no C8 N3 C1 N2 133.4(4) . . . . no C8 N3 C1 N1 -47.4(6) . . . . no C1 N3 C8 C7 163.5(4) . . . . no C5 N3 C8 C7 -38.3(4) . . . . no C1 N3 C8 C9 -79.6(5) . . . . no C5 N3 C8 C9 78.6(3) . . . . no C1 N3 C5 C4 83.3(5) . . . . no C8 N3 C5 C4 -75.3(4) . . . . no C1 N3 C5 C6 -154.0(4) . . . . no C8 N3 C5 C6 47.5(4) . . . . no N2 C2 C3 C4 3.7(7) . . . . no C2 C3 C4 C10 -96.2(5) . . . . no C2 C3 C4 C5 25.0(5) . . . . no C2 C3 C4 C11 145.6(4) . . . . no C10 C4 C5 N3 44.1(4) . . . . no C5 C4 C10 O1 164.9(3) . . . . no C3 C4 C5 C6 175.8(3) . . . . no C11 C4 C10 C9 -145.5(3) . . . . no C5 C4 C10 C9 -20.7(5) . . . . no C11 C4 C10 O1 40.1(5) . . . . no C3 C4 C10 C9 97.3(4) . . . . no C3 C4 C5 N3 -72.6(4) . . . . no C10 C4 C11 O2 -138.3(4) . . . . no C10 C4 C11 O3 44.8(4) . . . . no C10 C4 C5 C6 -67.4(4) . . . . no C11 C4 C5 N3 168.4(3) . . . . no C11 C4 C5 C6 56.9(4) . . . . no C3 C4 C10 O1 -77.2(4) . . . . no C5 C4 C11 O2 95.9(5) . . . . no C5 C4 C11 O3 -81.0(4) . . . . no C3 C4 C11 O2 -22.8(5) . . . . no C3 C4 C11 O3 160.4(3) . . . . no N3 C5 C6 C7 -37.2(4) . . . . no C4 C5 C6 C7 78.4(4) . . . . no C5 C6 C7 C8 14.7(4) . . . . no C6 C7 C8 N3 13.0(4) . . . . no C6 C7 C8 C9 -98.9(4) . . . . no N3 C8 C9 C10 -50.9(4) . . . . no C7 C8 C9 C10 59.4(4) . . . . no C8 C9 C10 O1 -160.9(4) . . . . no C8 C9 C10 C4 25.0(5) . . . . no O3 C12 C13 O4 31.6(5) . . . . no O3 C12 C13 O5 -148.0(3) . . . . no C15 C12 C13 O4 154.1(4) . . . . no C15 C12 C13 O5 -25.5(4) . . . . no O3 C12 C15 C14 153.5(3) . . . . no O3 C12 C15 C16 -87.9(4) . . . . no O3 C12 C15 C17 38.1(4) . . . . no C13 C12 C15 C14 36.5(4) . . . . no C13 C12 C15 C16 155.0(3) . . . . no C13 C12 C15 C17 -78.9(4) . . . . no O5 C14 C15 C12 -36.5(4) . . . . no O5 C14 C15 C16 -157.0(3) . . . . no O5 C14 C15 C17 79.3(4) . . . . no O6 C18 C19 F1 -27.3(5) . . . . no O6 C18 C19 F2 92.1(4) . . . . no O6 C18 C19 F3 -148.8(3) . . . . no O7 C18 C19 F1 156.0(3) . . . . no O7 C18 C19 F2 -84.6(5) . . . . no O7 C18 C19 F3 34.5(5) . . . . no