#------------------------------------------------------------------------------ #$Date: 2021-10-14 02:54:25 +0300 (Thu, 14 Oct 2021) $ #$Revision: 269928 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/37/7243738.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_7243738 loop_ _publ_author_name 'Luo, Mu-Jia' 'Ouyang, Xuan-Hui' 'Zhu, Yan-Ping' 'Li, Yang' 'Li, Jin-Heng' _publ_section_title ; Metal-Free Electrochemical [3+2] Heteroannulation of Anilines with Pyridines Enabled by Dual C-H Radical Aminations ; _journal_name_full 'Green Chemistry' _journal_paper_doi 10.1039/D1GC02922C _journal_year 2021 _chemical_formula_moiety C15H13FN2O3 _chemical_formula_sum 'C15 H13 F N2 O3' _chemical_formula_weight 288.27 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2021-01-17 deposited with the CCDC. 2021-10-12 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 93.00(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 12.35(3) _cell_length_b 13.16(3) _cell_length_c 8.567(18) _cell_measurement_reflns_used 1475 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 28.56 _cell_measurement_theta_min 2.26 _cell_volume 1390(5) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.967 _diffrn_measured_fraction_theta_max 0.966 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.2033 _diffrn_reflns_av_unetI/netI 0.2062 _diffrn_reflns_Laue_measured_fraction_full 0.967 _diffrn_reflns_Laue_measured_fraction_max 0.966 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 7959 _diffrn_reflns_point_group_measured_fraction_full 0.967 _diffrn_reflns_point_group_measured_fraction_max 0.966 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.494 _diffrn_reflns_theta_min 2.263 _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details sadabs _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.377 _exptl_crystal_description block _exptl_crystal_F_000 600 _exptl_crystal_size_max 0.160 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_min 0.140 _exptl_transmission_factor_max 1.0000 _exptl_transmission_factor_min 0.7512 _refine_diff_density_max 0.286 _refine_diff_density_min -0.273 _refine_diff_density_rms 0.082 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.160 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 192 _refine_ls_number_reflns 2498 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.160 _refine_ls_R_factor_all 0.2881 _refine_ls_R_factor_gt 0.1215 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0694P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1976 _refine_ls_wR_factor_ref 0.2314 _reflns_Friedel_coverage 0.000 _reflns_number_gt 923 _reflns_number_total 2498 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1gc02922c2.cif _cod_data_source_block A _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7243738 _shelx_shelxl_version_number 2014/7 _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 0.983 _shelx_estimated_absorpt_t_max 0.985 _shelx_res_file ; A.res created by SHELXL-2014/7 TITL A in P21/c CELL 0.71073 12.3500 13.1600 8.5670 90.000 93.000 90.000 ZERR 4 0.0300 0.0300 0.0180 0.000 0.030 0.000 LATT 1 SYMM - X , 0.50000 + Y , 0.50000 - Z SFAC C H N O F UNIT 60 52 8 12 4 OMIT -3 51 L.S. 20 ACTA BOND $H FMAP 2 PLAN 5 HTAB C1 F1_$1 HTAB C1 F1_$1 HTAB C1 F1_$1 HTAB C1 F1_$1 HTAB C1 F1_$1 HTAB C1 F1_$1 EQIV $1 -x+2, y+1/2, -z-1/2 htab size 0.14 0.15 0.16 CONF WGHT 0.069400 FVAR 0.08792 RESI 0 HTAB C1 F1_$1 HTAB C1 F1_$1 HTAB C1 F1_$1 HTAB C1 F1_$1 HTAB C1 F1_$1 TEMP 23 F1 5 0.948605 0.173135 -0.272986 11.00000 0.05751 0.06511 = 0.07108 -0.00127 0.00958 0.01414 N2 3 0.603834 0.233710 0.092982 11.00000 0.03794 0.02466 = 0.03259 0.00011 -0.01188 0.00043 N1 3 0.645194 0.068611 0.038385 11.00000 0.05732 0.03581 = 0.04755 -0.00211 -0.00232 -0.00097 O1 4 0.910023 0.362941 -0.209568 11.00000 0.05619 0.05564 = 0.06010 0.00222 0.00391 -0.00316 C6 1 0.693353 0.236752 0.001003 11.00000 0.03379 0.03591 = 0.02946 -0.00435 -0.01320 -0.00065 C8 1 0.545168 0.309771 0.159713 11.00000 0.04774 0.02506 = 0.03735 0.00228 -0.01147 -0.00868 AFIX 43 H8 2 0.564477 0.377189 0.144247 11.00000 -1.20000 AFIX 0 C9 1 0.577998 0.129387 0.113812 11.00000 0.04312 0.03062 = 0.04030 0.00242 -0.00935 -0.00236 C7 1 0.753658 0.318747 -0.056114 11.00000 0.03779 0.03803 = 0.03433 -0.00276 -0.00792 -0.00260 AFIX 43 H7 2 0.735726 0.385753 -0.034587 11.00000 -1.20000 AFIX 0 O2 4 0.314584 0.066453 0.407200 11.00000 0.08854 0.05087 = 0.07048 0.00093 0.00992 -0.02710 C13 1 0.338340 0.153632 0.369980 11.00000 0.05745 0.04680 = 0.04066 -0.00744 -0.01476 -0.01482 O3 4 0.279381 0.234574 0.411456 11.00000 0.05544 0.05081 = 0.04565 0.00075 0.00550 -0.01430 C12 1 0.459298 0.288226 0.248048 11.00000 0.03383 0.04061 = 0.03496 -0.00272 -0.01266 -0.00013 AFIX 43 H12 2 0.420086 0.340391 0.291746 11.00000 -1.20000 AFIX 0 C3 1 0.861763 0.191188 -0.180364 11.00000 0.04387 0.04358 = 0.03489 0.00452 -0.00787 0.00655 C10 1 0.488990 0.106906 0.204941 11.00000 0.05812 0.03398 = 0.04668 0.00391 -0.00779 -0.00328 AFIX 43 H10 2 0.469569 0.039437 0.219638 11.00000 -1.20000 AFIX 0 C4 1 0.805207 0.111870 -0.126045 11.00000 0.06891 0.03650 = 0.04707 -0.00217 -0.01005 0.00866 AFIX 43 H4 2 0.823240 0.045258 -0.149988 11.00000 -1.20000 AFIX 0 C2 1 0.839842 0.295506 -0.144723 11.00000 0.03535 0.04760 = 0.03594 0.00830 -0.01149 -0.00583 C11 1 0.429938 0.183070 0.272951 11.00000 0.04226 0.04153 = 0.03124 -0.00094 -0.01132 -0.01200 C15 1 0.137976 0.321410 0.539566 11.00000 0.06906 0.07242 = 0.07322 0.00986 0.01151 0.01064 AFIX 137 H15A 2 0.192162 0.362179 0.594152 11.00000 -1.50000 H15B 2 0.077038 0.313061 0.603499 11.00000 -1.50000 H15C 2 0.114835 0.354383 0.443577 11.00000 -1.50000 AFIX 0 C14 1 0.185291 0.217909 0.503904 11.00000 0.06199 0.07609 = 0.04350 0.00157 0.00323 -0.01983 AFIX 23 H14A 2 0.206613 0.182840 0.600253 11.00000 -1.20000 H14B 2 0.131913 0.176740 0.445881 11.00000 -1.20000 AFIX 0 C5 1 0.716987 0.133974 -0.030804 11.00000 0.04651 0.03153 = 0.03383 0.00255 -0.00930 -0.00060 C1 1 0.887562 0.468870 -0.185468 11.00000 0.07504 0.05037 = 0.09643 -0.00053 0.00876 -0.01955 AFIX 137 H1A 2 0.815983 0.484444 -0.227831 11.00000 -1.50000 H1B 2 0.939618 0.509372 -0.236950 11.00000 -1.50000 H1C 2 0.892095 0.483494 -0.075537 11.00000 -1.50000 AFIX 0 HKLF 4 1 0.0000 -1.0000 0.0000 0.0000 0.0000 1.0000 -1.0000 0.0000 0.0000 REM A in P21/c REM R1 = 0.1215 for 923 Fo > 4sig(Fo) and 0.2881 for all 2498 data REM 192 parameters refined using 0 restraints END WGHT 0.0694 0.0000 REM Instructions for potential hydrogen bonds HTAB C1 F1_$1 REM Highest difference peak 0.286, deepest hole -0.273, 1-sigma level 0.082 Q1 1 0.3631 0.2760 0.3078 11.00000 0.05 0.29 Q2 1 0.5016 0.2032 0.1829 11.00000 0.05 0.25 Q3 1 0.9979 0.3015 -0.2725 11.00000 0.05 0.25 Q4 1 0.9206 0.2920 -0.2152 11.00000 0.05 0.24 Q5 1 1.0220 0.1089 -0.3422 11.00000 0.05 0.24 ; _shelx_res_checksum 31330 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' 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 _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group F1 F 0.9486(3) 0.1731(3) -0.2730(4) 0.0643(12) Uani 1 1 d . . . . . N2 N 0.6038(4) 0.2337(4) 0.0930(5) 0.0322(13) Uani 1 1 d . . . . . N1 N 0.6452(5) 0.0686(4) 0.0384(6) 0.0471(15) Uani 1 1 d . . . . . O1 O 0.9100(4) 0.3629(4) -0.2096(5) 0.0573(14) Uani 1 1 d . . . . . C6 C 0.6934(5) 0.2368(5) 0.0010(7) 0.0336(16) Uani 1 1 d . . . . . C8 C 0.5452(5) 0.3098(5) 0.1597(7) 0.0372(17) Uani 1 1 d . . . . . H8 H 0.5645 0.3772 0.1442 0.045 Uiso 1 1 calc R U . . . C9 C 0.5780(5) 0.1294(5) 0.1138(7) 0.0384(17) Uani 1 1 d . . . . . C7 C 0.7537(5) 0.3187(5) -0.0561(6) 0.0371(17) Uani 1 1 d . . . . . H7 H 0.7357 0.3858 -0.0346 0.044 Uiso 1 1 calc R U . . . O2 O 0.3146(4) 0.0665(4) 0.4072(5) 0.0698(16) Uani 1 1 d . . . . . C13 C 0.3383(6) 0.1536(6) 0.3700(8) 0.049(2) Uani 1 1 d . . . . . O3 O 0.2794(4) 0.2346(3) 0.4115(5) 0.0505(13) Uani 1 1 d . . . . . C12 C 0.4593(5) 0.2882(5) 0.2480(7) 0.0370(17) Uani 1 1 d . . . . . H12 H 0.4201 0.3404 0.2917 0.044 Uiso 1 1 calc R U . . . C3 C 0.8618(5) 0.1912(5) -0.1804(7) 0.0411(18) Uani 1 1 d . . . . . C10 C 0.4890(5) 0.1069(5) 0.2049(7) 0.0466(19) Uani 1 1 d . . . . . H10 H 0.4696 0.0394 0.2196 0.056 Uiso 1 1 calc R U . . . C4 C 0.8052(6) 0.1119(5) -0.1260(7) 0.051(2) Uani 1 1 d . . . . . H4 H 0.8232 0.0453 -0.1500 0.062 Uiso 1 1 calc R U . . . C2 C 0.8398(5) 0.2955(5) -0.1447(7) 0.0401(18) Uani 1 1 d . . . . . C11 C 0.4299(5) 0.1831(5) 0.2730(7) 0.0388(18) Uani 1 1 d . . . . . C15 C 0.1380(6) 0.3214(6) 0.5396(8) 0.071(2) Uani 1 1 d . . . . . H15A H 0.1922 0.3622 0.5942 0.107 Uiso 1 1 calc R U . . . H15B H 0.0770 0.3131 0.6035 0.107 Uiso 1 1 calc R U . . . H15C H 0.1148 0.3544 0.4436 0.107 Uiso 1 1 calc R U . . . C14 C 0.1853(6) 0.2179(6) 0.5039(8) 0.061(2) Uani 1 1 d . . . . . H14A H 0.2066 0.1828 0.6003 0.073 Uiso 1 1 calc R U . . . H14B H 0.1319 0.1767 0.4459 0.073 Uiso 1 1 calc R U . . . C5 C 0.7170(5) 0.1340(5) -0.0308(7) 0.0377(17) Uani 1 1 d . . . . . C1 C 0.8876(6) 0.4689(5) -0.1855(8) 0.074(3) Uani 1 1 d . . . . . H1A H 0.8160 0.4844 -0.2278 0.111 Uiso 1 1 calc R U . . . H1B H 0.9396 0.5094 -0.2370 0.111 Uiso 1 1 calc R U . . . H1C H 0.8921 0.4835 -0.0755 0.111 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 0.058(3) 0.065(3) 0.071(3) -0.001(2) 0.010(2) 0.014(2) N2 0.038(4) 0.025(3) 0.033(3) 0.000(3) -0.012(3) 0.000(3) N1 0.057(4) 0.036(3) 0.048(3) -0.002(3) -0.002(3) -0.001(3) O1 0.056(3) 0.056(4) 0.060(3) 0.002(3) 0.004(3) -0.003(3) C6 0.034(4) 0.036(5) 0.029(4) -0.004(3) -0.013(3) -0.001(4) C8 0.048(5) 0.025(4) 0.037(4) 0.002(3) -0.011(4) -0.009(4) C9 0.043(5) 0.031(5) 0.040(4) 0.002(4) -0.009(4) -0.002(4) C7 0.038(4) 0.038(4) 0.034(4) -0.003(3) -0.008(4) -0.003(4) O2 0.089(4) 0.051(3) 0.070(4) 0.001(3) 0.010(3) -0.027(3) C13 0.057(6) 0.047(6) 0.041(4) -0.007(4) -0.015(4) -0.015(5) O3 0.055(3) 0.051(3) 0.046(3) 0.001(2) 0.005(3) -0.014(3) C12 0.034(4) 0.041(5) 0.035(4) -0.003(3) -0.013(3) 0.000(4) C3 0.044(5) 0.044(5) 0.035(4) 0.005(4) -0.008(4) 0.007(4) C10 0.058(5) 0.034(5) 0.047(4) 0.004(4) -0.008(4) -0.003(4) C4 0.069(6) 0.036(5) 0.047(5) -0.002(4) -0.010(4) 0.009(4) C2 0.035(5) 0.048(5) 0.036(4) 0.008(4) -0.011(4) -0.006(4) C11 0.042(5) 0.042(5) 0.031(4) -0.001(4) -0.011(4) -0.012(4) C15 0.069(6) 0.072(6) 0.073(5) 0.010(5) 0.012(4) 0.011(5) C14 0.062(5) 0.076(6) 0.043(4) 0.002(4) 0.003(4) -0.020(5) C5 0.047(5) 0.032(5) 0.034(4) 0.003(3) -0.009(4) -0.001(4) C1 0.075(6) 0.050(6) 0.096(6) -0.001(5) 0.009(5) -0.020(5) 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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 N2 C6 131.7(5) . . ? C8 N2 C9 121.5(5) . . ? C6 N2 C9 106.8(5) . . ? C9 N1 C5 105.1(5) . . ? C2 O1 C1 115.9(5) . . ? N2 C6 C7 131.8(6) . . ? N2 C6 C5 105.1(6) . . ? C7 C6 C5 123.1(6) . . ? C12 C8 N2 121.3(6) . . ? C12 C8 H8 119.3 . . ? N2 C8 H8 119.3 . . ? N1 C9 C10 131.3(6) . . ? N1 C9 N2 111.5(6) . . ? C10 C9 N2 117.2(6) . . ? C2 C7 C6 117.3(6) . . ? C2 C7 H7 121.3 . . ? C6 C7 H7 121.3 . . ? O2 C13 O3 121.9(7) . . ? O2 C13 C11 125.8(7) . . ? O3 C13 C11 112.2(6) . . ? C13 O3 C14 118.8(6) . . ? C8 C12 C11 119.2(6) . . ? C8 C12 H12 120.4 . . ? C11 C12 H12 120.4 . . ? C4 C3 F1 119.6(6) . . ? C4 C3 C2 124.0(7) . . ? F1 C3 C2 116.5(6) . . ? C11 C10 C9 121.5(6) . . ? C11 C10 H10 119.2 . . ? C9 C10 H10 119.2 . . ? C3 C4 C5 117.6(6) . . ? C3 C4 H4 121.2 . . ? C5 C4 H4 121.2 . . ? C7 C2 O1 127.0(6) . . ? C7 C2 C3 119.4(6) . . ? O1 C2 C3 113.6(6) . . ? C10 C11 C12 119.2(6) . . ? C10 C11 C13 118.6(6) . . ? C12 C11 C13 122.3(6) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O3 C14 C15 107.5(6) . . ? O3 C14 H14A 110.2 . . ? C15 C14 H14A 110.2 . . ? O3 C14 H14B 110.2 . . ? C15 C14 H14B 110.2 . . ? H14A C14 H14B 108.5 . . ? N1 C5 C6 111.5(6) . . ? N1 C5 C4 129.9(6) . . ? C6 C5 C4 118.5(6) . . ? O1 C1 H1A 109.5 . . ? O1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? 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 F1 C3 1.388(7) . ? N2 C8 1.377(7) . ? N2 C6 1.391(7) . ? N2 C9 1.423(8) . ? N1 C9 1.342(7) . ? N1 C5 1.390(7) . ? O1 C2 1.378(7) . ? O1 C1 1.438(8) . ? C6 C7 1.413(8) . ? C6 C5 1.413(8) . ? C8 C12 1.364(8) . ? C8 H8 0.9300 . ? C9 C10 1.413(8) . ? C7 C2 1.374(8) . ? C7 H7 0.9300 . ? O2 C13 1.230(8) . ? C13 O3 1.348(8) . ? C13 C11 1.490(9) . ? O3 C14 1.457(7) . ? C12 C11 1.449(8) . ? C12 H12 0.9300 . ? C3 C4 1.352(8) . ? C3 C2 1.435(9) . ? C10 C11 1.386(8) . ? C10 H10 0.9300 . ? C4 C5 1.425(8) . ? C4 H4 0.9300 . ? C15 C14 1.519(9) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? 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 C1 H1B F1 0.96 2.56 3.394(9) 145.6 2_754 C1 H1B F1 0.96 2.56 3.394(9) 145.6 2_754 C1 H1B F1 0.96 2.56 3.394(9) 145.6 2_754 C1 H1B F1 0.96 2.56 3.394(9) 145.6 2_754 C1 H1B F1 0.96 2.56 3.394(9) 145.6 2_754 C1 H1B F1 0.96 2.56 3.394(9) 145.6 2_754 C1 H1B F1 0.96 2.56 3.394(9) 145.6 2_754 C1 H1B F1 0.96 2.56 3.394(9) 145.6 2_754 C1 H1B F1 0.96 2.56 3.394(9) 145.6 2_754 C1 H1B F1 0.96 2.56 3.394(9) 145.6 2_754 C1 H1B F1 0.96 2.56 3.394(9) 145.6 2_754 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 C8 N2 C6 C7 -0.7(10) . . . . ? C9 N2 C6 C7 -179.8(6) . . . . ? C8 N2 C6 C5 179.7(6) . . . . ? C9 N2 C6 C5 0.5(6) . . . . ? C6 N2 C8 C12 -179.5(6) . . . . ? C9 N2 C8 C12 -0.4(8) . . . . ? C5 N1 C9 C10 -179.9(6) . . . . ? C5 N1 C9 N2 0.9(7) . . . . ? C8 N2 C9 N1 179.8(5) . . . . ? C6 N2 C9 N1 -0.9(6) . . . . ? C8 N2 C9 C10 0.5(8) . . . . ? C6 N2 C9 C10 179.8(5) . . . . ? N2 C6 C7 C2 179.5(6) . . . . ? C5 C6 C7 C2 -0.9(8) . . . . ? O2 C13 O3 C14 0.4(9) . . . . ? C11 C13 O3 C14 178.7(5) . . . . ? N2 C8 C12 C11 0.5(8) . . . . ? N1 C9 C10 C11 -179.9(6) . . . . ? N2 C9 C10 C11 -0.8(9) . . . . ? F1 C3 C4 C5 179.7(5) . . . . ? C2 C3 C4 C5 1.6(10) . . . . ? C6 C7 C2 O1 -178.9(5) . . . . ? C6 C7 C2 C3 2.6(8) . . . . ? C1 O1 C2 C7 -2.3(9) . . . . ? C1 O1 C2 C3 176.3(5) . . . . ? C4 C3 C2 C7 -3.1(10) . . . . ? F1 C3 C2 C7 178.7(5) . . . . ? C4 C3 C2 O1 178.2(6) . . . . ? F1 C3 C2 O1 0.0(8) . . . . ? C9 C10 C11 C12 0.9(9) . . . . ? C9 C10 C11 C13 -178.9(6) . . . . ? C8 C12 C11 C10 -0.7(9) . . . . ? C8 C12 C11 C13 179.0(6) . . . . ? O2 C13 C11 C10 6.4(10) . . . . ? O3 C13 C11 C10 -171.8(5) . . . . ? O2 C13 C11 C12 -173.4(6) . . . . ? O3 C13 C11 C12 8.4(8) . . . . ? C13 O3 C14 C15 177.4(6) . . . . ? C9 N1 C5 C6 -0.5(7) . . . . ? C9 N1 C5 C4 -179.6(6) . . . . ? N2 C6 C5 N1 0.0(6) . . . . ? C7 C6 C5 N1 -179.7(5) . . . . ? N2 C6 C5 C4 179.1(5) . . . . ? C7 C6 C5 C4 -0.5(9) . . . . ? C3 C4 C5 N1 179.2(6) . . . . ? C3 C4 C5 C6 0.2(9) . . . . ?