#------------------------------------------------------------------------------ #$Date: 2025-02-13 01:07:13 +0200 (Thu, 13 Feb 2025) $ #$Revision: 297708 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/38/1573891.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_1573891 loop_ _publ_author_name 'G\'orski, Krzysztof' 'Shelton, Steven' 'Lingagouder, Jaijanarthanan' 'Data, Przemys\/law' 'Jacquemin, Denis' 'Gryko, Daniel T.' _publ_section_title ; 1,4-Dihydropyrrolo[3,2-b]pyrrole modified with dibenzooxazepine: A Highly Efficient Core for Charge-Transfer-Based OLED Emitters ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D4SC04272G _journal_year 2025 _chemical_formula_moiety 'C38 H26 F8 N2 O2' _chemical_formula_sum 'C38 H26 F8 N2 O2' _chemical_formula_weight 694.61 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2014 _audit_update_record ; 2024-06-20 deposited with the CCDC. 2025-02-04 downloaded from the CCDC. ; _cell_angle_alpha 87.466(2) _cell_angle_beta 62.402(2) _cell_angle_gamma 89.609(2) _cell_formula_units_Z 1 _cell_length_a 9.4208(3) _cell_length_b 9.8930(3) _cell_length_c 9.9488(3) _cell_measurement_reflns_used 1680 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 68.36 _cell_measurement_theta_min 4.47 _cell_volume 820.83(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 (Sheldrick, 2014)' _computing_structure_solution 'SHELXL-2014 (Sheldrick, 2014)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.979 _diffrn_measured_fraction_theta_max 0.970 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0645 _diffrn_reflns_av_unetI/netI 0.0604 _diffrn_reflns_Laue_measured_fraction_full 0.979 _diffrn_reflns_Laue_measured_fraction_max 0.970 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 21362 _diffrn_reflns_point_group_measured_fraction_full 0.979 _diffrn_reflns_point_group_measured_fraction_max 0.970 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 68.361 _diffrn_reflns_theta_min 4.474 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 1.020 _exptl_absorpt_correction_T_max 0.8860 _exptl_absorpt_correction_T_min 0.7470 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details sadabs _exptl_crystal_colour colourless-yellow _exptl_crystal_density_diffrn 1.405 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 356 _exptl_crystal_size_max 0.304 _exptl_crystal_size_mid 0.174 _exptl_crystal_size_min 0.122 _refine_diff_density_max 0.394 _refine_diff_density_min -0.232 _refine_diff_density_rms 0.047 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 245 _refine_ls_number_reflns 2927 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.058 _refine_ls_R_factor_all 0.1118 _refine_ls_R_factor_gt 0.0549 _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^)+(0.0608P)^2^+0.3215P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1297 _refine_ls_wR_factor_ref 0.1549 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1680 _reflns_number_total 2927 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4sc04272g2.cif _cod_data_source_block KGO0172_2a_0m _cod_database_code 1573891 _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 0.747 _shelx_estimated_absorpt_t_max 0.886 _shelxl_version_number 2014-3 _shelx_res_file ; TITL KGO0172_2a_0m in P-1 CELL 1.54178 9.4208 9.8930 9.9488 87.466 62.402 89.609 ZERR 1.00 0.0003 0.0003 0.0003 0.002 0.002 0.002 LATT 1 SFAC C H N O F UNIT 38 26 2 2 8 MERG 2 L.S. 20 ACTA BOND $H FMAP 2 PLAN -4 HTAB CONF SIZE 0.122 0.174 0.304 TEMP 23.000 WGHT 0.060800 0.321500 FVAR 0.25413 F1 5 0.130706 0.675486 1.127727 11.00000 0.05635 0.05931 = 0.07944 0.00129 -0.01173 -0.01174 F2 5 0.068645 0.426424 1.080874 11.00000 0.08619 0.06511 = 0.11423 0.02304 -0.04885 -0.03416 F3 5 0.297869 0.279942 0.863452 11.00000 0.15173 0.04654 = 0.12828 -0.00789 -0.07944 -0.02181 F4 5 0.595977 0.388312 0.696367 11.00000 0.13318 0.04667 = 0.07248 -0.01830 -0.03656 0.01568 O1 4 0.674738 0.631505 0.752399 11.00000 0.06024 0.04301 = 0.04688 0.00222 -0.01876 0.00933 N1 3 0.557001 0.886811 0.857737 11.00000 0.04787 0.03656 = 0.02975 -0.00030 -0.01140 -0.00359 C1 1 0.632474 1.133215 0.895468 11.00000 0.04625 0.03973 = 0.03304 0.00255 -0.01105 -0.00604 C2 1 0.556066 1.006046 0.925421 11.00000 0.04512 0.03674 = 0.02792 -0.00106 -0.01050 -0.00232 C3 1 0.437830 0.801666 0.969937 11.00000 0.04605 0.03527 = 0.03605 0.00088 -0.01476 -0.00274 C4 1 0.401659 0.667143 0.939794 11.00000 0.05468 0.03469 = 0.03806 0.00091 -0.02145 -0.00247 C5 1 0.250054 0.607338 1.020186 11.00000 0.05668 0.04464 = 0.04898 0.00312 -0.02065 -0.00142 C6 1 0.216010 0.479177 0.996572 11.00000 0.07102 0.04558 = 0.07246 0.01475 -0.03826 -0.02014 C7 1 0.330437 0.406081 0.887941 11.00000 0.10302 0.03429 = 0.07848 0.00076 -0.05574 -0.01170 C8 1 0.482047 0.460787 0.803660 11.00000 0.09139 0.03671 = 0.04970 -0.00687 -0.03422 0.00850 C9 1 0.517477 0.588599 0.830554 11.00000 0.06153 0.03613 = 0.04216 0.00304 -0.02392 0.00003 C10 1 0.700878 0.740645 0.648618 11.00000 0.05006 0.03955 = 0.03902 -0.00095 -0.01608 0.00366 C11 1 0.643971 0.866819 0.699935 11.00000 0.03925 0.04298 = 0.02836 -0.00389 -0.01230 0.00076 C12 1 0.679449 0.974768 0.594970 11.00000 0.04190 0.04065 = 0.03246 -0.00151 -0.01147 0.00017 C13 1 0.773349 0.959068 0.440905 11.00000 0.04359 0.05178 = 0.03307 -0.00147 -0.01435 0.00019 C14 1 0.826757 0.830025 0.393615 11.00000 0.06606 0.05964 = 0.03081 -0.00700 -0.01114 0.00543 C15 1 0.790195 0.721635 0.496292 11.00000 0.07200 0.04781 = 0.04522 -0.00876 -0.01569 0.01257 C16 1 0.823148 1.079091 0.324965 11.00000 0.05218 0.05579 = 0.04124 0.00551 -0.01544 -0.00226 C17 1 0.798948 1.041397 0.188113 11.00000 0.11921 0.10284 = 0.05395 0.01098 -0.04108 0.00848 AFIX 137 H17A 2 0.830871 1.116512 0.115247 11.00000 -1.50000 H17B 2 0.688039 1.019777 0.221944 11.00000 -1.50000 H17C 2 0.862871 0.964438 0.141959 11.00000 -1.50000 AFIX 0 C18 1 0.999397 1.105094 0.267560 11.00000 0.07918 0.12654 = 0.17339 0.08170 -0.05725 -0.05082 AFIX 137 H18A 2 1.038977 1.165257 0.179017 11.00000 -1.50000 H18B 2 1.055368 1.021105 0.241979 11.00000 -1.50000 H18C 2 1.016308 1.145513 0.345054 11.00000 -1.50000 AFIX 0 C19 1 0.723144 1.201429 0.387209 11.00000 0.13874 0.05893 = 0.05625 0.00877 -0.01575 0.01447 AFIX 137 H19A 2 0.747673 1.238709 0.461639 11.00000 -1.50000 H19B 2 0.611754 1.176104 0.433626 11.00000 -1.50000 H19C 2 0.745947 1.267841 0.306233 11.00000 -1.50000 AFIX 0 H1 2 0.718178 1.172979 0.799487 11.00000 0.05410 H12 2 0.633202 1.061732 0.631783 11.00000 0.03515 H14 2 0.892925 0.816050 0.281760 11.00000 0.05808 H15 2 0.825431 0.629243 0.464306 11.00000 0.07242 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM KGO0172_2a_0m in P-1 REM R1 = 0.0549 for 1680 Fo > 4sig(Fo) and 0.1118 for all 2927 data REM 245 parameters refined using 0 restraints END WGHT 0.0620 0.3133 REM No hydrogen bonds found for HTAB generation REM Highest difference peak 0.394, deepest hole -0.232, 1-sigma level 0.047 Q1 1 0.9065 1.1965 0.3925 11.00000 0.05 0.39 Q2 1 0.9329 1.0589 0.1711 11.00000 0.05 0.27 Q3 1 1.0336 1.2360 0.2341 11.00000 0.05 0.17 Q4 1 0.8130 1.2897 0.3040 11.00000 0.05 0.16 ; _shelx_res_checksum 73939 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 _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group F1 F 0.1307(2) 0.67549(18) 1.1277(2) 0.0729(6) Uani 1 1 d . . . . . F2 F 0.0686(2) 0.42642(19) 1.0809(3) 0.0883(7) Uani 1 1 d . . . . . F3 F 0.2979(3) 0.27994(19) 0.8635(3) 0.1029(8) Uani 1 1 d . . . . . F4 F 0.5960(3) 0.38831(18) 0.6964(2) 0.0880(7) Uani 1 1 d . . . . . O1 O 0.6747(2) 0.63150(19) 0.7524(2) 0.0526(6) Uani 1 1 d . . . . . N1 N 0.5570(3) 0.8868(2) 0.8577(2) 0.0407(6) Uani 1 1 d . . . . . C1 C 0.6325(4) 1.1332(3) 0.8955(3) 0.0427(7) Uani 1 1 d . . . . . C2 C 0.5561(3) 1.0060(3) 0.9254(3) 0.0391(7) Uani 1 1 d . . . . . C3 C 0.4378(3) 0.8017(3) 0.9699(3) 0.0409(7) Uani 1 1 d . . . . . C4 C 0.4017(4) 0.6671(3) 0.9398(3) 0.0426(7) Uani 1 1 d . . . . . C5 C 0.2501(4) 0.6073(3) 1.0202(4) 0.0518(8) Uani 1 1 d . . . . . C6 C 0.2160(4) 0.4792(3) 0.9966(4) 0.0615(9) Uani 1 1 d . . . . . C7 C 0.3304(5) 0.4061(3) 0.8879(4) 0.0666(10) Uani 1 1 d . . . . . C8 C 0.4820(5) 0.4608(3) 0.8037(4) 0.0585(9) Uani 1 1 d . . . . . C9 C 0.5175(4) 0.5886(3) 0.8306(3) 0.0468(8) Uani 1 1 d . . . . . C10 C 0.7009(4) 0.7406(3) 0.6486(3) 0.0447(7) Uani 1 1 d . . . . . C11 C 0.6440(3) 0.8668(3) 0.6999(3) 0.0381(7) Uani 1 1 d . . . . . C12 C 0.6794(3) 0.9748(3) 0.5950(3) 0.0406(7) Uani 1 1 d . . . . . C13 C 0.7733(3) 0.9591(3) 0.4409(3) 0.0442(7) Uani 1 1 d . . . . . C14 C 0.8268(4) 0.8300(3) 0.3936(4) 0.0565(9) Uani 1 1 d . . . . . C15 C 0.7902(4) 0.7216(3) 0.4963(4) 0.0594(9) Uani 1 1 d . . . . . C16 C 0.8231(4) 1.0791(3) 0.3250(3) 0.0524(8) Uani 1 1 d . . . . . C17 C 0.7989(5) 1.0414(4) 0.1881(4) 0.0921(13) Uani 1 1 d . . . . . H17A H 0.8309 1.1165 0.1152 0.138 Uiso 1 1 calc R U . . . H17B H 0.6880 1.0198 0.2219 0.138 Uiso 1 1 calc R U . . . H17C H 0.8629 0.9644 0.1420 0.138 Uiso 1 1 calc R U . . . C18 C 0.9994(5) 1.1051(5) 0.2676(6) 0.130(2) Uani 1 1 d . . . . . H18A H 1.0390 1.1653 0.1790 0.194 Uiso 1 1 calc R U . . . H18B H 1.0554 1.0211 0.2420 0.194 Uiso 1 1 calc R U . . . H18C H 1.0163 1.1455 0.3451 0.194 Uiso 1 1 calc R U . . . C19 C 0.7231(5) 1.2014(3) 0.3872(4) 0.0967(15) Uani 1 1 d . . . . . H19A H 0.7477 1.2387 0.4616 0.145 Uiso 1 1 calc R U . . . H19B H 0.6118 1.1761 0.4336 0.145 Uiso 1 1 calc R U . . . H19C H 0.7459 1.2678 0.3062 0.145 Uiso 1 1 calc R U . . . H1 H 0.718(3) 1.173(3) 0.799(3) 0.054(8) Uiso 1 1 d . . . . . H12 H 0.633(3) 1.062(2) 0.632(3) 0.035(7) Uiso 1 1 d . . . . . H14 H 0.893(3) 0.816(3) 0.282(4) 0.058(9) Uiso 1 1 d . . . . . H15 H 0.825(4) 0.629(3) 0.464(3) 0.072(10) Uiso 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 F1 0.0564(12) 0.0593(12) 0.0794(14) 0.0013(10) -0.0117(11) -0.0117(9) F2 0.0862(15) 0.0651(13) 0.1142(18) 0.0230(12) -0.0489(14) -0.0342(11) F3 0.152(2) 0.0465(12) 0.128(2) -0.0079(12) -0.0794(18) -0.0218(12) F4 0.1332(19) 0.0467(11) 0.0725(14) -0.0183(10) -0.0366(14) 0.0157(12) O1 0.0602(14) 0.0430(12) 0.0469(13) 0.0022(10) -0.0188(12) 0.0093(10) N1 0.0479(14) 0.0366(13) 0.0297(14) -0.0003(10) -0.0114(12) -0.0036(11) C1 0.0463(18) 0.0397(17) 0.0330(18) 0.0025(14) -0.0110(16) -0.0060(14) C2 0.0451(17) 0.0367(16) 0.0279(14) -0.0011(12) -0.0105(13) -0.0023(13) C3 0.0461(18) 0.0353(16) 0.0360(17) 0.0009(13) -0.0148(15) -0.0027(13) C4 0.0547(19) 0.0347(16) 0.0381(17) 0.0009(13) -0.0214(16) -0.0025(14) C5 0.057(2) 0.0446(19) 0.049(2) 0.0031(15) -0.0206(18) -0.0014(16) C6 0.071(2) 0.046(2) 0.072(3) 0.0148(18) -0.038(2) -0.0201(18) C7 0.103(3) 0.0343(19) 0.078(3) 0.0008(18) -0.056(3) -0.012(2) C8 0.091(3) 0.0367(18) 0.050(2) -0.0069(15) -0.034(2) 0.0085(18) C9 0.062(2) 0.0361(17) 0.0422(19) 0.0030(14) -0.0239(17) 0.0000(15) C10 0.0501(18) 0.0395(17) 0.0390(18) -0.0009(14) -0.0161(16) 0.0037(14) C11 0.0392(16) 0.0430(17) 0.0284(16) -0.0039(13) -0.0123(14) 0.0008(13) C12 0.0419(17) 0.0407(18) 0.0325(18) -0.0015(13) -0.0115(15) 0.0002(14) C13 0.0436(17) 0.0518(19) 0.0331(18) -0.0015(14) -0.0143(15) 0.0002(14) C14 0.066(2) 0.060(2) 0.0308(19) -0.0070(16) -0.0111(18) 0.0054(17) C15 0.072(2) 0.048(2) 0.045(2) -0.0088(17) -0.0157(19) 0.0126(18) C16 0.0522(19) 0.056(2) 0.0412(19) 0.0055(15) -0.0154(16) -0.0023(16) C17 0.119(4) 0.103(3) 0.054(2) 0.011(2) -0.041(3) 0.008(3) C18 0.079(3) 0.127(4) 0.173(5) 0.082(4) -0.057(3) -0.051(3) C19 0.139(4) 0.059(2) 0.056(2) 0.0088(19) -0.016(3) 0.014(2) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 '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 C9 O1 C10 114.0(2) . . ? C2 N1 C3 106.8(2) . . ? C2 N1 C11 124.8(2) . . ? C3 N1 C11 127.7(2) . . ? C3 C1 C2 106.1(2) 2_677 . ? C3 C1 H1 124.4(16) 2_677 . ? C2 C1 H1 129.5(16) . . ? C2 C2 N1 108.4(3) 2_677 . ? C2 C2 C1 109.4(3) 2_677 . ? N1 C2 C1 142.1(2) . . ? C1 C3 N1 109.2(2) 2_677 . ? C1 C3 C4 128.1(2) 2_677 . ? N1 C3 C4 122.7(2) . . ? C9 C4 C5 115.7(3) . . ? C9 C4 C3 122.0(3) . . ? C5 C4 C3 122.3(3) . . ? F1 C5 C6 117.3(3) . . ? F1 C5 C4 119.9(3) . . ? C6 C5 C4 122.8(3) . . ? F2 C6 C7 120.1(3) . . ? F2 C6 C5 119.7(3) . . ? C7 C6 C5 120.1(3) . . ? F3 C7 C6 120.6(4) . . ? F3 C7 C8 119.9(4) . . ? C6 C7 C8 119.5(3) . . ? F4 C8 C7 119.7(3) . . ? F4 C8 C9 120.1(3) . . ? C7 C8 C9 120.3(3) . . ? O1 C9 C8 117.0(3) . . ? O1 C9 C4 121.3(3) . . ? C8 C9 C4 121.5(3) . . ? C15 C10 C11 120.7(3) . . ? C15 C10 O1 119.1(3) . . ? C11 C10 O1 120.1(2) . . ? C10 C11 C12 118.9(3) . . ? C10 C11 N1 120.4(2) . . ? C12 C11 N1 120.7(2) . . ? C13 C12 C11 121.6(3) . . ? C13 C12 H12 120.2(14) . . ? C11 C12 H12 118.2(14) . . ? C12 C13 C14 117.8(3) . . ? C12 C13 C16 122.1(3) . . ? C14 C13 C16 120.1(3) . . ? C15 C14 C13 121.3(3) . . ? C15 C14 H14 119.8(16) . . ? C13 C14 H14 119.0(16) . . ? C10 C15 C14 119.8(3) . . ? C10 C15 H15 118.0(18) . . ? C14 C15 H15 122.2(18) . . ? C19 C16 C18 113.3(3) . . ? C19 C16 C13 112.7(3) . . ? C18 C16 C13 107.8(3) . . ? C19 C16 C17 105.9(3) . . ? C18 C16 C17 107.4(3) . . ? C13 C16 C17 109.6(3) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 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 C5 1.342(3) . ? F2 C6 1.340(4) . ? F3 C7 1.346(3) . ? F4 C8 1.342(4) . ? O1 C9 1.375(4) . ? O1 C10 1.401(3) . ? N1 C2 1.382(3) . ? N1 C3 1.409(3) . ? N1 C11 1.417(3) . ? C1 C3 1.377(4) 2_677 ? C1 C2 1.404(4) . ? C1 H1 0.99(3) . ? C2 C2 1.366(5) 2_677 ? C3 C1 1.377(4) 2_677 ? C3 C4 1.454(4) . ? C4 C9 1.393(4) . ? C4 C5 1.393(4) . ? C5 C6 1.367(4) . ? C6 C7 1.354(5) . ? C7 C8 1.377(5) . ? C8 C9 1.378(4) . ? C10 C15 1.372(4) . ? C10 C11 1.378(4) . ? C11 C12 1.388(4) . ? C12 C13 1.385(4) . ? C12 H12 0.97(2) . ? C13 C14 1.389(4) . ? C13 C16 1.532(4) . ? C14 C15 1.376(4) . ? C14 H14 1.01(3) . ? C15 H15 0.99(3) . ? C16 C19 1.499(4) . ? C16 C18 1.505(5) . ? C16 C17 1.542(5) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? 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 C3 N1 C2 C2 1.6(4) . . . 2_677 ? C11 N1 C2 C2 172.2(3) . . . 2_677 ? C3 N1 C2 C1 179.4(4) . . . . ? C11 N1 C2 C1 -10.0(6) . . . . ? C3 C1 C2 C2 -0.7(4) 2_677 . . 2_677 ? C3 C1 C2 N1 -178.5(4) 2_677 . . . ? C2 N1 C3 C1 -1.1(3) . . . 2_677 ? C11 N1 C3 C1 -171.4(3) . . . 2_677 ? C2 N1 C3 C4 178.9(3) . . . . ? C11 N1 C3 C4 8.7(4) . . . . ? C1 C3 C4 C9 -150.1(3) 2_677 . . . ? N1 C3 C4 C9 29.8(4) . . . . ? C1 C3 C4 C5 28.5(5) 2_677 . . . ? N1 C3 C4 C5 -151.5(3) . . . . ? C9 C4 C5 F1 -180.0(3) . . . . ? C3 C4 C5 F1 1.3(4) . . . . ? C9 C4 C5 C6 1.1(4) . . . . ? C3 C4 C5 C6 -177.6(3) . . . . ? F1 C5 C6 F2 -0.8(5) . . . . ? C4 C5 C6 F2 178.2(3) . . . . ? F1 C5 C6 C7 178.8(3) . . . . ? C4 C5 C6 C7 -2.2(5) . . . . ? F2 C6 C7 F3 -0.1(5) . . . . ? C5 C6 C7 F3 -179.7(3) . . . . ? F2 C6 C7 C8 -179.0(3) . . . . ? C5 C6 C7 C8 1.3(5) . . . . ? F3 C7 C8 F4 0.7(5) . . . . ? C6 C7 C8 F4 179.7(3) . . . . ? F3 C7 C8 C9 -178.4(3) . . . . ? C6 C7 C8 C9 0.6(5) . . . . ? C10 O1 C9 C8 114.2(3) . . . . ? C10 O1 C9 C4 -70.2(3) . . . . ? F4 C8 C9 O1 -5.2(4) . . . . ? C7 C8 C9 O1 173.9(3) . . . . ? F4 C8 C9 C4 179.2(3) . . . . ? C7 C8 C9 C4 -1.6(5) . . . . ? C5 C4 C9 O1 -174.6(3) . . . . ? C3 C4 C9 O1 4.2(4) . . . . ? C5 C4 C9 C8 0.8(4) . . . . ? C3 C4 C9 C8 179.6(3) . . . . ? C9 O1 C10 C15 -113.8(3) . . . . ? C9 O1 C10 C11 69.4(3) . . . . ? C15 C10 C11 C12 -0.5(4) . . . . ? O1 C10 C11 C12 176.3(3) . . . . ? C15 C10 C11 N1 -177.6(3) . . . . ? O1 C10 C11 N1 -0.8(4) . . . . ? C2 N1 C11 C10 149.4(3) . . . . ? C3 N1 C11 C10 -42.0(4) . . . . ? C2 N1 C11 C12 -27.7(4) . . . . ? C3 N1 C11 C12 141.0(3) . . . . ? C10 C11 C12 C13 -1.5(4) . . . . ? N1 C11 C12 C13 175.6(3) . . . . ? C11 C12 C13 C14 2.2(4) . . . . ? C11 C12 C13 C16 -175.6(3) . . . . ? C12 C13 C14 C15 -1.1(5) . . . . ? C16 C13 C14 C15 176.8(3) . . . . ? C11 C10 C15 C14 1.5(5) . . . . ? O1 C10 C15 C14 -175.3(3) . . . . ? C13 C14 C15 C10 -0.7(5) . . . . ? C12 C13 C16 C19 -17.1(4) . . . . ? C14 C13 C16 C19 165.1(3) . . . . ? C12 C13 C16 C18 108.7(4) . . . . ? C14 C13 C16 C18 -69.1(4) . . . . ? C12 C13 C16 C17 -134.7(3) . . . . ? C14 C13 C16 C17 47.5(4) . . . . ?