#------------------------------------------------------------------------------ #$Date: 2019-11-08 03:40:58 +0200 (Fri, 08 Nov 2019) $ #$Revision: 225148 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/66/7156652.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_7156652 loop_ _publ_author_name 'Motornov, Vladimir A.' 'Tabolin, Andrey A.' 'Nelyubina, Yulia V.' 'Nenajdenko, Valentine G.' 'Ioffe, Sema L.' _publ_section_title ; Copper-mediated oxidative [3 + 2]-annulation of nitroalkenes and pyridinium ylides: general access to functionalized indolizines and efficient synthesis of 1-fluoroindolizines. ; _journal_issue 6 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 1442 _journal_page_last 1454 _journal_paper_doi 10.1039/c8ob03126f _journal_volume 17 _journal_year 2019 _chemical_formula_moiety 'C16 H11 F N2 O' _chemical_formula_sum 'C16 H11 F N2 O' _chemical_formula_weight 266.27 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2014/6 _audit_update_record ; 2018-12-07 deposited with the CCDC. 2019-01-15 downloaded from the CCDC. ; _cell_angle_alpha 92.690(3) _cell_angle_beta 99.941(3) _cell_angle_gamma 114.170(3) _cell_formula_units_Z 4 _cell_length_a 8.3168(9) _cell_length_b 9.3791(12) _cell_length_c 18.018(2) _cell_measurement_reflns_used 2624 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 30 _cell_measurement_theta_min 3 _cell_volume 1252.1(3) _computing_cell_refinement 'APEX2 (Bruker, 2005)' _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_data_reduction 'APEX2 (Bruker, 2005)' _computing_molecular_graphics 'SHELXL-2014/6 (Sheldrick, 2014)' _computing_publication_material 'SHELXL-2014/6 (Sheldrick, 2014)' _computing_structure_refinement 'SHELXL-2014/6 (Sheldrick, 2014)' _computing_structure_solution 'APEX2 (Bruker, 2005)' _diffrn_ambient_temperature 120(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.992 _diffrn_measurement_device_type 'Bruker APEX2 DUO CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0444 _diffrn_reflns_av_unetI/netI 0.0799 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.992 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_number 12347 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.992 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.999 _diffrn_reflns_theta_min 2.315 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_T_max 0.7461 _exptl_absorpt_correction_T_min 0.6814 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'APEX2 (Bruker, 2005)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.412 _exptl_crystal_description prism _exptl_crystal_F_000 552 _exptl_crystal_size_max 0.350 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_min 0.010 _refine_diff_density_max 0.327 _refine_diff_density_min -0.332 _refine_diff_density_rms 0.066 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 363 _refine_ls_number_reflns 6613 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.001 _refine_ls_R_factor_all 0.0951 _refine_ls_R_factor_gt 0.0576 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0620P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1240 _refine_ls_wR_factor_ref 0.1484 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4177 _reflns_number_total 6613 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c8ob03126f2.cif _cod_data_source_block 1 _cod_depositor_comments 'Adding full bibliography for 7156652.cif.' _cod_database_code 7156652 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_min 0.966 _shelx_estimated_absorpt_t_max 0.999 _shelxl_version_number 2014/6 _shelx_res_file ; TITL a_a.res in P-1 CELL 0.71073 8.3168 9.3791 18.0178 92.690 99.941 114.170 ZERR 4.00 0.0009 0.0012 0.0021 0.003 0.003 0.003 LATT 1 SFAC C H N O F UNIT 64 44 8 4 4 TEMP -153.000 size 0.01 0.15 0.35 L.S. 10 BOND $H htab conf omit -4 58 omit 0 0 1 acta FMAP 2 PLAN 20 WGHT 0.062000 FVAR 0.12035 F1 5 0.715960 -0.213672 0.686745 11.00000 0.02568 0.02145 = 0.02145 -0.00375 -0.00353 0.00815 O1 4 0.548647 0.369517 0.562540 11.00000 0.02005 0.01929 = 0.02170 0.00453 -0.00253 0.00777 N1 3 1.003364 -0.010044 0.861225 11.00000 0.01706 0.01847 = 0.01709 0.00287 0.00138 0.00775 N2 3 1.114501 0.384988 0.908787 11.00000 0.03730 0.02586 = 0.02516 0.00030 -0.00537 0.01469 C1 1 0.850573 0.050526 0.759553 11.00000 0.01545 0.01620 = 0.01611 0.00266 0.00400 0.00482 C2 1 0.968602 0.110455 0.831038 11.00000 0.01850 0.01930 = 0.01703 0.00343 0.00282 0.00927 C3 1 1.109584 -0.006478 0.929686 11.00000 0.02283 0.02331 = 0.01872 0.00125 -0.00126 0.01186 AFIX 43 H3A 2 1.176030 0.089626 0.962854 11.00000 -1.20000 AFIX 0 C4 1 1.118445 -0.140726 0.949240 11.00000 0.02633 0.03015 = 0.01986 0.00609 0.00111 0.01621 AFIX 43 H4A 2 1.191008 -0.138532 0.996576 11.00000 -1.20000 AFIX 0 C5 1 1.020857 -0.285169 0.900068 11.00000 0.02774 0.02361 = 0.03066 0.00838 0.00889 0.01677 AFIX 43 H5A 2 1.026914 -0.379057 0.914838 11.00000 -1.20000 AFIX 0 C6 1 0.918662 -0.288619 0.831735 11.00000 0.02001 0.01867 = 0.02647 0.00237 0.00598 0.00817 AFIX 43 H6A 2 0.854672 -0.384584 0.798295 11.00000 -1.20000 AFIX 0 C7 1 0.908018 -0.148628 0.810633 11.00000 0.01785 0.01747 = 0.01911 0.00143 0.00576 0.00677 C8 1 0.818175 -0.108979 0.748957 11.00000 0.01649 0.01842 = 0.01547 0.00012 0.00243 0.00548 C9 1 1.046881 0.262572 0.872687 11.00000 0.02112 0.02290 = 0.01633 0.00358 -0.00110 0.01079 C10 1 0.771609 0.134025 0.708553 11.00000 0.01536 0.01891 = 0.01441 0.00268 0.00349 0.00723 C11 1 0.603496 0.050310 0.660190 11.00000 0.01574 0.01606 = 0.02059 0.00360 0.00299 0.00400 AFIX 43 H11A 2 0.542161 -0.060106 0.660664 11.00000 -1.20000 AFIX 0 C12 1 0.523241 0.124371 0.611236 11.00000 0.01516 0.02036 = 0.02016 0.00344 0.00011 0.00561 AFIX 43 H12A 2 0.408383 0.065215 0.578955 11.00000 -1.20000 AFIX 0 C13 1 0.613403 0.286439 0.610122 11.00000 0.01746 0.01911 = 0.01530 0.00457 0.00428 0.00883 C14 1 0.780543 0.372290 0.658610 11.00000 0.01912 0.01576 = 0.01939 0.00164 0.00083 0.00336 AFIX 43 H14A 2 0.841480 0.482811 0.658344 11.00000 -1.20000 AFIX 0 C15 1 0.858112 0.296818 0.707234 11.00000 0.01652 0.01930 = 0.01787 0.00108 -0.00070 0.00408 AFIX 43 H15A 2 0.971859 0.356575 0.740205 11.00000 -1.20000 AFIX 0 C16 1 0.390451 0.279885 0.504990 11.00000 0.02100 0.02500 = 0.01966 0.00434 -0.00210 0.01094 AFIX 137 H16A 2 0.359128 0.351436 0.473883 11.00000 -1.50000 H16B 2 0.290223 0.220385 0.529034 11.00000 -1.50000 H16C 2 0.413838 0.206549 0.472704 11.00000 -1.50000 AFIX 0 F1A 5 0.253586 0.276974 0.669455 11.00000 0.03038 0.02178 = 0.01868 -0.00435 -0.00575 0.01104 O1A 4 0.072809 0.856568 0.549318 11.00000 0.02059 0.02417 = 0.01534 0.00452 0.00141 0.01288 N1A 3 0.499372 0.466117 0.852399 11.00000 0.01615 0.01517 = 0.01656 0.00204 0.00094 0.00740 N2A 3 0.581940 0.852438 0.906467 11.00000 0.03883 0.02335 = 0.02397 0.00098 -0.00172 0.01707 C1A 1 0.362524 0.531376 0.747242 11.00000 0.01407 0.01846 = 0.01513 0.00265 0.00235 0.00639 C2A 1 0.461730 0.585770 0.822715 11.00000 0.01704 0.01637 = 0.01741 0.00297 0.00222 0.00803 C3A 1 0.591750 0.465755 0.923495 11.00000 0.02210 0.02152 = 0.01514 0.00105 -0.00175 0.00989 AFIX 43 H3AA 2 0.641775 0.557018 0.960156 11.00000 -1.20000 AFIX 0 C4A 1 0.610285 0.333521 0.940418 11.00000 0.02787 0.02416 = 0.01866 0.00336 -0.00104 0.01259 AFIX 43 H4AA 2 0.673538 0.332392 0.989457 11.00000 -1.20000 AFIX 0 C5A 1 0.536589 0.196030 0.885970 11.00000 0.03148 0.02176 = 0.02795 0.00511 0.00095 0.01615 AFIX 43 H5AA 2 0.549103 0.103576 0.899006 11.00000 -1.20000 AFIX 0 C6A 1 0.448363 0.197406 0.815354 11.00000 0.02299 0.01813 = 0.02424 -0.00171 -0.00178 0.00925 AFIX 43 H6AA 2 0.401527 0.106749 0.778481 11.00000 -1.20000 AFIX 0 C7A 1 0.426350 0.334334 0.796818 11.00000 0.01794 0.01709 = 0.01883 0.00038 0.00316 0.00812 C8A 1 0.345418 0.377637 0.734016 11.00000 0.01713 0.01767 = 0.01392 -0.00160 -0.00040 0.00591 C9A 1 0.525903 0.733948 0.867526 11.00000 0.02132 0.02414 = 0.01535 0.00532 0.00088 0.01239 C10A 1 0.289450 0.616776 0.695222 11.00000 0.01278 0.01541 = 0.01829 0.00304 0.00198 0.00438 C11A 1 0.277194 0.590797 0.616975 11.00000 0.01711 0.01474 = 0.01817 0.00157 0.00290 0.00598 AFIX 43 H11B 2 0.319890 0.519683 0.597985 11.00000 -1.20000 AFIX 0 C12A 1 0.203964 0.666627 0.566300 11.00000 0.01678 0.01965 = 0.01359 0.00091 0.00249 0.00580 AFIX 43 H12B 2 0.195558 0.646279 0.513289 11.00000 -1.20000 AFIX 0 C13A 1 0.143099 0.772401 0.593626 11.00000 0.01161 0.01506 = 0.01860 0.00358 -0.00004 0.00404 C14A 1 0.154248 0.799816 0.671836 11.00000 0.01510 0.01846 = 0.01934 0.00092 0.00293 0.00792 AFIX 43 H14B 2 0.111897 0.871332 0.690669 11.00000 -1.20000 AFIX 0 C15A 1 0.226527 0.723408 0.721787 11.00000 0.01519 0.02023 = 0.01432 0.00154 0.00304 0.00640 AFIX 43 H15B 2 0.233727 0.743262 0.774724 11.00000 -1.20000 AFIX 0 C16A 1 0.072894 0.839988 0.469672 11.00000 0.02051 0.02560 = 0.01522 0.00419 0.00105 0.01053 AFIX 137 H16D 2 0.023268 0.907709 0.444243 11.00000 -1.50000 H16E 2 -0.001198 0.729915 0.447507 11.00000 -1.50000 H16F 2 0.196672 0.871028 0.462922 11.00000 -1.50000 AFIX 0 HKLF 4 REM a_a.res in P-1 REM R1 = 0.0576 for 4177 Fo > 4sig(Fo) and 0.0951 for all 6613 data REM 363 parameters refined using 0 restraints END WGHT 0.0591 0.0000 REM Instructions for potential hydrogen bonds EQIV $1 -x+2, -y+1, -z+2 HTAB C3 N2A_$1 EQIV $2 x, y-1, z HTAB C12 O1A_$2 EQIV $3 -x+1, -y+1, -z+1 HTAB C16 O1_$3 EQIV $4 -x, -y+2, -z+1 HTAB C16A O1A_$4 REM Highest difference peak 0.327, deepest hole -0.332, 1-sigma level 0.066 Q1 1 0.3711 0.5576 0.7935 11.00000 0.05 0.33 Q2 1 0.3455 0.4599 0.7190 11.00000 0.05 0.31 Q3 1 0.3820 0.2478 0.8024 11.00000 0.05 0.29 Q4 1 1.1797 -0.0603 0.9299 11.00000 0.05 0.28 Q5 1 0.5939 0.2001 0.5975 11.00000 0.05 0.28 Q6 1 0.8217 0.2048 0.7000 11.00000 0.05 0.26 Q7 1 0.5662 0.2177 0.6357 11.00000 0.05 0.25 Q8 1 0.6625 0.4226 0.9265 11.00000 0.05 0.25 Q9 1 0.4479 0.5244 0.8383 11.00000 0.05 0.25 Q10 1 0.8839 0.0788 0.8027 11.00000 0.05 0.25 Q11 1 0.6839 0.3380 0.6400 11.00000 0.05 0.24 Q12 1 0.2498 0.5806 0.6562 11.00000 0.05 0.24 Q13 1 0.2053 0.0603 0.5213 11.00000 0.05 0.24 Q14 1 0.0444 0.9563 0.4692 11.00000 0.05 0.24 Q15 1 0.8578 -0.0349 0.7367 11.00000 0.05 0.23 Q16 1 0.8050 0.3133 0.6793 11.00000 0.05 0.23 Q17 1 1.0082 0.2752 0.9125 11.00000 0.05 0.23 Q18 1 0.4752 0.6427 0.8461 11.00000 0.05 0.23 Q19 1 0.9623 0.1208 0.7888 11.00000 0.05 0.23 Q20 1 0.9737 -0.2043 0.8202 11.00000 0.05 0.23 ; _shelx_res_checksum 91329 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp F1 F 0.71596(17) -0.21367(13) 0.68674(6) 0.0248(3) Uani 1 1 d . . O1 O 0.54865(19) 0.36952(16) 0.56254(7) 0.0214(3) Uani 1 1 d . . N1 N 1.0034(2) -0.01004(19) 0.86122(9) 0.0177(4) Uani 1 1 d . . N2 N 1.1145(3) 0.3850(2) 0.90879(10) 0.0307(5) Uani 1 1 d . . C1 C 0.8506(3) 0.0505(2) 0.75955(10) 0.0165(4) Uani 1 1 d . . C2 C 0.9686(3) 0.1105(2) 0.83104(11) 0.0179(4) Uani 1 1 d . . C3 C 1.1096(3) -0.0065(2) 0.92969(11) 0.0217(4) Uani 1 1 d . . H3A H 1.1760 0.0896 0.9629 0.026 Uiso 1 1 calc R U C4 C 1.1184(3) -0.1407(3) 0.94924(12) 0.0244(5) Uani 1 1 d . . H4A H 1.1910 -0.1385 0.9966 0.029 Uiso 1 1 calc R U C5 C 1.0209(3) -0.2852(3) 0.90007(12) 0.0248(5) Uani 1 1 d . . H5A H 1.0269 -0.3791 0.9148 0.030 Uiso 1 1 calc R U C6 C 0.9187(3) -0.2886(2) 0.83174(11) 0.0216(4) Uani 1 1 d . . H6A H 0.8547 -0.3846 0.7983 0.026 Uiso 1 1 calc R U C7 C 0.9080(3) -0.1486(2) 0.81063(11) 0.0182(4) Uani 1 1 d . . C8 C 0.8182(3) -0.1090(2) 0.74896(10) 0.0176(4) Uani 1 1 d . . C9 C 1.0469(3) 0.2626(2) 0.87269(11) 0.0203(4) Uani 1 1 d . . C10 C 0.7716(3) 0.1340(2) 0.70855(10) 0.0162(4) Uani 1 1 d . . C11 C 0.6035(3) 0.0503(2) 0.66019(11) 0.0185(4) Uani 1 1 d . . H11A H 0.5422 -0.0601 0.6607 0.022 Uiso 1 1 calc R U C12 C 0.5232(3) 0.1244(2) 0.61124(11) 0.0197(4) Uani 1 1 d . . H12A H 0.4084 0.0652 0.5790 0.024 Uiso 1 1 calc R U C13 C 0.6134(3) 0.2864(2) 0.61012(10) 0.0167(4) Uani 1 1 d . . C14 C 0.7805(3) 0.3723(2) 0.65861(11) 0.0199(4) Uani 1 1 d . . H14A H 0.8415 0.4828 0.6583 0.024 Uiso 1 1 calc R U C15 C 0.8581(3) 0.2968(2) 0.70723(11) 0.0197(4) Uani 1 1 d . . H15A H 0.9719 0.3566 0.7402 0.024 Uiso 1 1 calc R U C16 C 0.3905(3) 0.2799(2) 0.50499(11) 0.0223(4) Uani 1 1 d . . H16A H 0.3591 0.3514 0.4739 0.033 Uiso 1 1 calc R U H16B H 0.2902 0.2204 0.5290 0.033 Uiso 1 1 calc R U H16C H 0.4138 0.2065 0.4727 0.033 Uiso 1 1 calc R U F1A F 0.25359(17) 0.27697(14) 0.66945(6) 0.0253(3) Uani 1 1 d . . O1A O 0.07281(19) 0.85657(16) 0.54932(7) 0.0191(3) Uani 1 1 d . . N1A N 0.4994(2) 0.46612(18) 0.85240(9) 0.0160(3) Uani 1 1 d . . N2A N 0.5819(3) 0.8524(2) 0.90647(10) 0.0286(4) Uani 1 1 d . . C1A C 0.3625(3) 0.5314(2) 0.74724(10) 0.0161(4) Uani 1 1 d . . C2A C 0.4617(3) 0.5858(2) 0.82272(10) 0.0168(4) Uani 1 1 d . . C3A C 0.5918(3) 0.4658(2) 0.92350(11) 0.0202(4) Uani 1 1 d . . H3AA H 0.6418 0.5570 0.9602 0.024 Uiso 1 1 calc R U C4A C 0.6103(3) 0.3335(2) 0.94042(11) 0.0238(5) Uani 1 1 d . . H4AA H 0.6735 0.3324 0.9895 0.029 Uiso 1 1 calc R U C5A C 0.5366(3) 0.1960(3) 0.88597(12) 0.0261(5) Uani 1 1 d . . H5AA H 0.5491 0.1036 0.8990 0.031 Uiso 1 1 calc R U C6A C 0.4484(3) 0.1974(2) 0.81535(11) 0.0227(5) Uani 1 1 d . . H6AA H 0.4015 0.1067 0.7785 0.027 Uiso 1 1 calc R U C7A C 0.4263(3) 0.3343(2) 0.79682(11) 0.0179(4) Uani 1 1 d . . C8A C 0.3454(3) 0.3776(2) 0.73402(10) 0.0174(4) Uani 1 1 d . . C9A C 0.5259(3) 0.7339(2) 0.86753(11) 0.0196(4) Uani 1 1 d . . C10A C 0.2894(3) 0.6168(2) 0.69522(10) 0.0162(4) Uani 1 1 d . . C11A C 0.2772(3) 0.5908(2) 0.61697(10) 0.0171(4) Uani 1 1 d . . H11B H 0.3199 0.5197 0.5980 0.020 Uiso 1 1 calc R U C12A C 0.2040(3) 0.6666(2) 0.56630(10) 0.0175(4) Uani 1 1 d . . H12B H 0.1956 0.6463 0.5133 0.021 Uiso 1 1 calc R U C13A C 0.1431(3) 0.7724(2) 0.59363(10) 0.0160(4) Uani 1 1 d . . C14A C 0.1542(3) 0.7998(2) 0.67184(10) 0.0175(4) Uani 1 1 d . . H14B H 0.1119 0.8713 0.6907 0.021 Uiso 1 1 calc R U C15A C 0.2265(3) 0.7234(2) 0.72179(10) 0.0170(4) Uani 1 1 d . . H15B H 0.2337 0.7433 0.7747 0.020 Uiso 1 1 calc R U C16A C 0.0729(3) 0.8400(2) 0.46967(10) 0.0205(4) Uani 1 1 d . . H16D H 0.0233 0.9077 0.4442 0.031 Uiso 1 1 calc R U H16E H -0.0012 0.7299 0.4475 0.031 Uiso 1 1 calc R U H16F H 0.1967 0.8710 0.4629 0.031 Uiso 1 1 calc R U loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.0257(7) 0.0214(6) 0.0215(6) -0.0038(5) -0.0035(5) 0.0081(5) O1 0.0201(8) 0.0193(7) 0.0217(7) 0.0045(6) -0.0025(6) 0.0078(6) N1 0.0171(9) 0.0185(8) 0.0171(8) 0.0029(6) 0.0014(7) 0.0077(7) N2 0.0373(12) 0.0259(10) 0.0252(10) 0.0003(8) -0.0054(8) 0.0147(9) C1 0.0154(10) 0.0162(9) 0.0161(9) 0.0027(7) 0.0040(8) 0.0048(8) C2 0.0185(11) 0.0193(10) 0.0170(9) 0.0034(7) 0.0028(8) 0.0093(9) C3 0.0228(12) 0.0233(11) 0.0187(10) 0.0013(8) -0.0013(8) 0.0119(9) C4 0.0263(12) 0.0301(12) 0.0199(10) 0.0061(9) 0.0011(9) 0.0162(10) C5 0.0277(13) 0.0236(11) 0.0307(12) 0.0084(9) 0.0089(10) 0.0168(10) C6 0.0200(11) 0.0187(10) 0.0265(11) 0.0024(8) 0.0060(9) 0.0082(9) C7 0.0178(11) 0.0175(10) 0.0191(10) 0.0014(7) 0.0058(8) 0.0068(8) C8 0.0165(10) 0.0184(10) 0.0155(9) 0.0001(7) 0.0024(8) 0.0055(8) C9 0.0211(11) 0.0229(11) 0.0163(10) 0.0036(8) -0.0011(8) 0.0108(9) C10 0.0154(10) 0.0189(10) 0.0144(9) 0.0027(7) 0.0035(8) 0.0072(8) C11 0.0157(11) 0.0161(9) 0.0206(10) 0.0036(7) 0.0030(8) 0.0040(8) C12 0.0152(11) 0.0204(10) 0.0202(10) 0.0034(8) 0.0001(8) 0.0056(8) C13 0.0175(11) 0.0191(10) 0.0153(9) 0.0046(7) 0.0043(8) 0.0088(8) C14 0.0191(11) 0.0158(9) 0.0194(10) 0.0016(8) 0.0008(8) 0.0034(8) C15 0.0165(11) 0.0193(10) 0.0179(10) 0.0011(8) -0.0007(8) 0.0041(8) C16 0.0210(12) 0.0250(11) 0.0197(10) 0.0043(8) -0.0021(8) 0.0109(9) F1A 0.0304(7) 0.0218(6) 0.0187(6) -0.0043(5) -0.0057(5) 0.0110(6) O1A 0.0206(8) 0.0242(7) 0.0153(7) 0.0045(5) 0.0014(6) 0.0129(6) N1A 0.0162(9) 0.0152(8) 0.0166(8) 0.0020(6) 0.0009(7) 0.0074(7) N2A 0.0388(12) 0.0233(10) 0.0240(9) 0.0010(8) -0.0017(8) 0.0171(9) C1A 0.0141(10) 0.0185(9) 0.0151(9) 0.0027(7) 0.0023(7) 0.0064(8) C2A 0.0170(10) 0.0164(9) 0.0174(9) 0.0030(7) 0.0022(8) 0.0080(8) C3A 0.0221(11) 0.0215(10) 0.0151(9) 0.0010(8) -0.0017(8) 0.0099(9) C4A 0.0279(13) 0.0242(11) 0.0187(10) 0.0034(8) -0.0010(9) 0.0126(10) C5A 0.0315(13) 0.0218(11) 0.0280(11) 0.0051(9) 0.0009(10) 0.0161(10) C6A 0.0230(12) 0.0181(10) 0.0242(11) -0.0017(8) -0.0018(9) 0.0092(9) C7A 0.0179(11) 0.0171(10) 0.0188(10) 0.0004(7) 0.0032(8) 0.0081(8) C8A 0.0171(11) 0.0177(10) 0.0139(9) -0.0016(7) -0.0004(8) 0.0059(8) C9A 0.0213(11) 0.0241(11) 0.0153(9) 0.0053(8) 0.0009(8) 0.0124(9) C10A 0.0128(10) 0.0154(9) 0.0183(9) 0.0030(7) 0.0020(8) 0.0044(8) C11A 0.0171(10) 0.0147(9) 0.0182(9) 0.0016(7) 0.0029(8) 0.0060(8) C12A 0.0168(11) 0.0197(10) 0.0136(9) 0.0009(7) 0.0025(8) 0.0058(8) C13A 0.0116(10) 0.0151(9) 0.0186(9) 0.0036(7) 0.0000(8) 0.0040(8) C14A 0.0151(10) 0.0185(10) 0.0193(10) 0.0009(7) 0.0029(8) 0.0079(8) C15A 0.0152(10) 0.0202(10) 0.0143(9) 0.0015(7) 0.0030(8) 0.0064(8) C16A 0.0205(11) 0.0256(11) 0.0152(9) 0.0042(8) 0.0011(8) 0.0105(9) 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C13 O1 C16 116.93(15) C3 N1 C2 129.36(17) C3 N1 C7 121.46(17) C2 N1 C7 109.17(16) C8 C1 C2 104.66(17) C8 C1 C10 127.42(18) C2 C1 C10 127.87(18) N1 C2 C1 108.94(17) N1 C2 C9 119.96(17) C1 C2 C9 131.09(18) C4 C3 N1 119.45(19) C4 C3 H3A 120.3 N1 C3 H3A 120.3 C3 C4 C5 121.0(2) C3 C4 H4A 119.5 C5 C4 H4A 119.5 C6 C5 C4 119.78(19) C6 C5 H5A 120.1 C4 C5 H5A 120.1 C5 C6 C7 119.78(19) C5 C6 H6A 120.1 C7 C6 H6A 120.1 C8 C7 N1 105.76(16) C8 C7 C6 135.68(19) N1 C7 C6 118.54(18) F1 C8 C7 122.55(17) F1 C8 C1 125.98(18) C7 C8 C1 111.47(17) N2 C9 C2 177.4(2) C11 C10 C15 117.92(18) C11 C10 C1 119.72(17) C15 C10 C1 122.35(18) C12 C11 C10 121.73(18) C12 C11 H11A 119.1 C10 C11 H11A 119.1 C11 C12 C13 119.28(19) C11 C12 H12A 120.4 C13 C12 H12A 120.4 O1 C13 C14 116.38(17) O1 C13 C12 123.82(18) C14 C13 C12 119.80(18) C15 C14 C13 120.17(18) C15 C14 H14A 119.9 C13 C14 H14A 119.9 C14 C15 C10 121.09(19) C14 C15 H15A 119.5 C10 C15 H15A 119.5 O1 C16 H16A 109.5 O1 C16 H16B 109.5 H16A C16 H16B 109.5 O1 C16 H16C 109.5 H16A C16 H16C 109.5 H16B C16 H16C 109.5 C13A O1A C16A 116.80(15) C3A N1A C2A 129.28(16) C3A N1A C7A 121.84(16) C2A N1A C7A 108.88(15) C8A C1A C2A 104.57(16) C8A C1A C10A 127.91(17) C2A C1A C10A 127.50(18) N1A C2A C1A 108.92(16) N1A C2A C9A 119.83(17) C1A C2A C9A 131.23(18) C4A C3A N1A 119.03(18) C4A C3A H3AA 120.5 N1A C3A H3AA 120.5 C3A C4A C5A 121.12(19) C3A C4A H4AA 119.4 C5A C4A H4AA 119.4 C6A C5A C4A 119.83(19) C6A C5A H5AA 120.1 C4A C5A H5AA 120.1 C5A C6A C7A 119.84(19) C5A C6A H6AA 120.1 C7A C6A H6AA 120.1 C8A C7A N1A 105.59(16) C8A C7A C6A 136.08(18) N1A C7A C6A 118.33(17) F1A C8A C7A 122.48(17) F1A C8A C1A 125.40(17) C7A C8A C1A 112.03(17) N2A C9A C2A 177.1(2) C11A C10A C15A 118.03(17) C11A C10A C1A 120.35(17) C15A C10A C1A 121.61(17) C12A C11A C10A 121.54(18) C12A C11A H11B 119.2 C10A C11A H11B 119.2 C11A C12A C13A 119.66(17) C11A C12A H12B 120.2 C13A C12A H12B 120.2 O1A C13A C12A 124.73(17) O1A C13A C14A 115.69(17) C12A C13A C14A 119.57(17) C15A C14A C13A 120.39(18) C15A C14A H14B 119.8 C13A C14A H14B 119.8 C14A C15A C10A 120.81(17) C14A C15A H15B 119.6 C10A C15A H15B 119.6 O1A C16A H16D 109.5 O1A C16A H16E 109.5 H16D C16A H16E 109.5 O1A C16A H16F 109.5 H16D C16A H16F 109.5 H16E C16A H16F 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance F1 C8 1.352(2) O1 C13 1.371(2) O1 C16 1.433(2) N1 C3 1.378(3) N1 C2 1.388(2) N1 C7 1.394(2) N2 C9 1.154(3) C1 C8 1.404(3) C1 C2 1.408(3) C1 C10 1.473(3) C2 C9 1.412(3) C3 C4 1.350(3) C3 H3A 0.9500 C4 C5 1.420(3) C4 H4A 0.9500 C5 C6 1.361(3) C5 H5A 0.9500 C6 C7 1.417(3) C6 H6A 0.9500 C7 C8 1.382(3) C10 C11 1.395(3) C10 C15 1.400(3) C11 C12 1.393(3) C11 H11A 0.9500 C12 C13 1.396(3) C12 H12A 0.9500 C13 C14 1.394(3) C14 C15 1.386(3) C14 H14A 0.9500 C15 H15A 0.9500 C16 H16A 0.9800 C16 H16B 0.9800 C16 H16C 0.9800 F1A C8A 1.352(2) O1A C13A 1.370(2) O1A C16A 1.436(2) N1A C3A 1.376(2) N1A C2A 1.389(2) N1A C7A 1.399(2) N2A C9A 1.155(3) C1A C8A 1.394(3) C1A C2A 1.412(3) C1A C10A 1.470(3) C2A C9A 1.417(3) C3A C4A 1.353(3) C3A H3AA 0.9500 C4A C5A 1.424(3) C4A H4AA 0.9500 C5A C6A 1.358(3) C5A H5AA 0.9500 C6A C7A 1.416(3) C6A H6AA 0.9500 C7A C8A 1.379(3) C10A C11A 1.398(3) C10A C15A 1.405(3) C11A C12A 1.391(3) C11A H11B 0.9500 C12A C13A 1.391(3) C12A H12B 0.9500 C13A C14A 1.401(3) C14A C15A 1.383(3) C14A H14B 0.9500 C15A H15B 0.9500 C16A H16D 0.9800 C16A H16E 0.9800 C16A H16F 0.9800 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 C3 N1 C2 C1 -179.53(19) C7 N1 C2 C1 -0.6(2) C3 N1 C2 C9 -0.4(3) C7 N1 C2 C9 178.56(17) C8 C1 C2 N1 -0.2(2) C10 C1 C2 N1 177.28(18) C8 C1 C2 C9 -179.2(2) C10 C1 C2 C9 -1.7(4) C2 N1 C3 C4 177.2(2) C7 N1 C3 C4 -1.6(3) N1 C3 C4 C5 0.4(3) C3 C4 C5 C6 0.9(3) C4 C5 C6 C7 -1.0(3) C3 N1 C7 C8 -179.84(18) C2 N1 C7 C8 1.1(2) C3 N1 C7 C6 1.5(3) C2 N1 C7 C6 -177.54(17) C5 C6 C7 C8 -178.3(2) C5 C6 C7 N1 -0.2(3) N1 C7 C8 F1 177.59(17) C6 C7 C8 F1 -4.1(4) N1 C7 C8 C1 -1.3(2) C6 C7 C8 C1 177.0(2) C2 C1 C8 F1 -177.90(18) C10 C1 C8 F1 4.6(3) C2 C1 C8 C7 0.9(2) C10 C1 C8 C7 -176.57(18) C8 C1 C10 C11 26.4(3) C2 C1 C10 C11 -150.5(2) C8 C1 C10 C15 -154.5(2) C2 C1 C10 C15 28.6(3) C15 C10 C11 C12 0.6(3) C1 C10 C11 C12 179.73(17) C10 C11 C12 C13 0.3(3) C16 O1 C13 C14 171.21(17) C16 O1 C13 C12 -7.8(3) C11 C12 C13 O1 177.99(17) C11 C12 C13 C14 -1.0(3) O1 C13 C14 C15 -178.35(17) C12 C13 C14 C15 0.7(3) C13 C14 C15 C10 0.3(3) C11 C10 C15 C14 -0.9(3) C1 C10 C15 C14 180.00(18) C3A N1A C2A C1A -179.78(19) C7A N1A C2A C1A 0.3(2) C3A N1A C2A C9A 1.6(3) C7A N1A C2A C9A -178.32(18) C8A C1A C2A N1A -0.5(2) C10A C1A C2A N1A 177.92(18) C8A C1A C2A C9A 177.9(2) C10A C1A C2A C9A -3.7(4) C2A N1A C3A C4A 179.2(2) C7A N1A C3A C4A -0.9(3) N1A C3A C4A C5A 0.2(3) C3A C4A C5A C6A 1.0(3) C4A C5A C6A C7A -1.5(3) C3A N1A C7A C8A -179.87(17) C2A N1A C7A C8A 0.1(2) C3A N1A C7A C6A 0.4(3) C2A N1A C7A C6A -179.65(18) C5A C6A C7A C8A -178.8(2) C5A C6A C7A N1A 0.8(3) N1A C7A C8A F1A -177.31(17) C6A C7A C8A F1A 2.3(4) N1A C7A C8A C1A -0.4(2) C6A C7A C8A C1A 179.2(2) C2A C1A C8A F1A 177.37(18) C10A C1A C8A F1A -1.1(3) C2A C1A C8A C7A 0.6(2) C10A C1A C8A C7A -177.85(19) C8A C1A C10A C11A -34.4(3) C2A C1A C10A C11A 147.6(2) C8A C1A C10A C15A 144.2(2) C2A C1A C10A C15A -33.8(3) C15A C10A C11A C12A -0.5(3) C1A C10A C11A C12A 178.16(18) C10A C11A C12A C13A 0.8(3) C16A O1A C13A C12A -3.9(3) C16A O1A C13A C14A 175.27(17) C11A C12A C13A O1A 178.32(18) C11A C12A C13A C14A -0.8(3) O1A C13A C14A C15A -178.67(17) C12A C13A C14A C15A 0.5(3) C13A C14A C15A C10A -0.2(3) C11A C10A C15A C14A 0.2(3) C1A C10A C15A C14A -178.43(18)