#------------------------------------------------------------------------------ #$Date: 2024-09-19 02:37:09 +0300 (Thu, 19 Sep 2024) $ #$Revision: 294786 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/93/7249350.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_7249350 loop_ _publ_author_name 'Zi, Jingjing' 'Tang, Huiling' 'Wang, Dongyin' 'Li, Meng' 'Zhou, Yuxiang' 'Lv, Sihui' 'Liang, Deqiang' 'Shi, Lou' _publ_section_title ; Electrochemically enabled dearomative [2+2] cycloadditions of indoles with alkynes to access cyclobutene-fused indolines ; _journal_name_full 'Green Chemistry' _journal_paper_doi 10.1039/D4GC04126G _journal_year 2024 _chemical_formula_moiety 'C21 H18 F N O3' _chemical_formula_sum 'C21 H18 F N O3' _chemical_formula_weight 351.36 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2022-11-01 _audit_creation_method ; Olex2 1.5 (compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498) ; _audit_update_record ; 2024-06-30 deposited with the CCDC. 2024-09-17 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 108.318(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 12.5984(6) _cell_length_b 10.5934(5) _cell_length_c 13.2326(6) _cell_measurement_reflns_used 9983 _cell_measurement_temperature 100.0(2) _cell_measurement_theta_max 56.98 _cell_measurement_theta_min 3.68 _cell_volume 1676.53(14) _computing_cell_refinement 'SAINT V8.40B (?, 2016)' _computing_data_collection 'Apex3 (Bruker 2018)' _computing_data_reduction 'SAINT V8.40B (?, 2016)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2019/2 (Sheldrick, 2015)' _computing_structure_solution 'ShelXT 2014' _diffrn_ambient_temperature 100.0(2) _diffrn_detector 'Bruker PHOTON III area detector' _diffrn_detector_area_resol_mean 7.9 _diffrn_detector_type 'CMOS area detector' _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker D8 VENTURE' _diffrn_measurement_method '\w and \f scans' _diffrn_radiation_monochromator 'mirror optics' _diffrn_radiation_probe x-ray _diffrn_radiation_type GaK\a _diffrn_radiation_wavelength 1.34139 _diffrn_reflns_av_R_equivalents 0.0412 _diffrn_reflns_av_unetI/netI 0.0214 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.995 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 35685 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.995 _diffrn_reflns_theta_full 53.594 _diffrn_reflns_theta_max 57.116 _diffrn_reflns_theta_min 3.677 _diffrn_source 'microfocus Metaljet' _diffrn_source_current 3.0 _diffrn_source_power 0.20955 _diffrn_source_type 'Incoatec Metaljet' _diffrn_source_voltage 69.85 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.529 _exptl_absorpt_correction_T_max 0.7512 _exptl_absorpt_correction_T_min 0.7109 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0729 before and 0.0536 after correction. The Ratio of minimum to maximum transmission is 0.9464. The \l/2 correction factor is Not present. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.392 _exptl_crystal_description block _exptl_crystal_F_000 736 _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _refine_diff_density_max 0.325 _refine_diff_density_min -0.194 _refine_diff_density_rms 0.041 _refine_ls_extinction_coef 0.0062(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2019/2 (Sheldrick 2019)' _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 238 _refine_ls_number_reflns 3434 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.030 _refine_ls_R_factor_all 0.0362 _refine_ls_R_factor_gt 0.0329 _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^)+(0.0384P)^2^+0.7591P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0815 _refine_ls_wR_factor_ref 0.0832 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3134 _reflns_number_total 3434 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4gc04126g2.cif _cod_data_source_block cxy5046_0m _cod_database_code 7249350 _shelx_shelxl_version_number 2019/2 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Ternary CH refined with riding coordinates: C7(H7) 2.b Secondary CH2 refined with riding coordinates: C9(H9A,H9B) 2.c Aromatic/amide H refined with riding coordinates: C2(H2), C3(H3), C6(H6), C12(H12), C13(H13), C17(H17), C18(H18), C19(H19), C20(H20) 2.d Idealised Me refined as rotating group: C11(H11A,H11B,H11C), C21(H21A,H21B,H21C) ; _shelx_res_file ; TITL cxy5046_0m_a.res in P2(1)/n cxy5046_0m.res created by SHELXL-2019/2 at 16:26:31 on 01-Nov-2022 CELL 1.34139 12.5984 10.5934 13.2326 90 108.318 90 ZERR 4 0.0006 0.0005 0.0006 0 0.002 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H N O F DISP C 0.0137 0.0067 57.1 DISP F 0.0583 0.04 317.7 DISP H 0 0 0.6 DISP N 0.0241 0.0134 109.9 DISP O 0.0389 0.0241 193.4 UNIT 84 72 4 12 4 L.S. 4 PLAN 5 0 0 TEMP -173.15 CONF HTAB BOND $H fmap 2 acta MORE -1 REM REM REM WGHT 0.038400 0.759100 EXTI 0.006200 FVAR 0.83625 F1 5 0.816518 0.320905 0.833861 11.00000 0.03158 0.04179 = 0.02182 0.01212 0.01417 0.00726 O1 4 0.914227 0.720112 0.117071 11.00000 0.02499 0.01640 = 0.02132 -0.00173 0.01049 -0.00328 O2 4 0.674383 0.533269 0.017375 11.00000 0.01892 0.02037 = 0.01376 0.00012 0.00367 -0.00174 O3 4 0.935404 0.643514 -0.033647 11.00000 0.03266 0.02389 = 0.02325 0.00341 0.01720 0.00164 N1 3 0.754712 0.541394 0.196934 11.00000 0.01324 0.01716 = 0.01372 -0.00004 0.00405 0.00062 C1 1 0.824584 0.362279 0.738768 11.00000 0.01689 0.03289 = 0.01626 0.00760 0.00614 0.00250 C2 1 0.836319 0.274199 0.666439 11.00000 0.01796 0.02144 = 0.02315 0.00493 0.00513 -0.00053 AFIX 43 H2 2 0.839565 0.186555 0.682331 11.00000 -1.20000 AFIX 0 C3 1 0.843259 0.317263 0.569687 11.00000 0.01554 0.01909 = 0.01899 -0.00099 0.00380 -0.00108 AFIX 43 H3 2 0.851400 0.258126 0.518656 11.00000 -1.20000 AFIX 0 C4 1 0.838474 0.446345 0.545952 11.00000 0.01224 0.01950 = 0.01505 0.00013 0.00180 -0.00034 C5 1 0.844421 0.487740 0.442351 11.00000 0.01250 0.01567 = 0.01618 -0.00048 0.00145 -0.00058 C6 1 0.874107 0.431504 0.364236 11.00000 0.01592 0.01810 = 0.01575 -0.00063 0.00190 0.00248 AFIX 43 H6 2 0.899339 0.348745 0.356143 11.00000 -1.20000 AFIX 0 C7 1 0.852941 0.547162 0.293930 11.00000 0.01429 0.01794 = 0.01322 -0.00089 0.00342 -0.00015 AFIX 13 H7 2 0.921371 0.585183 0.283436 11.00000 -1.20000 AFIX 0 C8 1 0.757847 0.527142 0.095878 11.00000 0.01789 0.01060 = 0.01525 0.00031 0.00590 -0.00128 C9 1 0.871032 0.505776 0.080297 11.00000 0.01961 0.01538 = 0.01620 -0.00009 0.00765 0.00127 AFIX 23 H9A 2 0.925541 0.476087 0.147648 11.00000 -1.20000 H9B 2 0.864542 0.440391 0.025222 11.00000 -1.20000 AFIX 0 C10 1 0.910980 0.628635 0.046161 11.00000 0.01351 0.01821 = 0.01747 0.00097 0.00532 0.00252 C11 1 0.948493 0.843733 0.092338 11.00000 0.02348 0.01561 = 0.03200 0.00069 0.01003 -0.00249 AFIX 137 H11A 2 1.025283 0.839396 0.089709 11.00000 -1.50000 H11B 2 0.944942 0.903893 0.147446 11.00000 -1.50000 H11C 2 0.898441 0.871567 0.023123 11.00000 -1.50000 AFIX 0 C12 1 0.820886 0.490446 0.720127 11.00000 0.02376 0.02901 = 0.01754 -0.00074 0.00715 0.00525 AFIX 43 H12 2 0.814260 0.548656 0.772428 11.00000 -1.20000 AFIX 0 C13 1 0.827157 0.532129 0.622261 11.00000 0.02174 0.01945 = 0.01873 0.00035 0.00574 0.00297 AFIX 43 H13 2 0.823698 0.619988 0.607183 11.00000 -1.20000 AFIX 0 C14 1 0.812097 0.613221 0.381483 11.00000 0.01619 0.01468 = 0.01405 -0.00036 0.00438 0.00029 C15 1 0.687679 0.623744 0.327501 11.00000 0.01677 0.01240 = 0.01518 0.00077 0.00399 -0.00050 C16 1 0.657435 0.576462 0.223435 11.00000 0.01684 0.01265 = 0.01591 0.00081 0.00663 0.00089 C17 1 0.546172 0.566954 0.160818 11.00000 0.01751 0.01697 = 0.01430 0.00009 0.00382 0.00011 AFIX 43 H17 2 0.526064 0.531711 0.091336 11.00000 -1.20000 AFIX 0 C18 1 0.465010 0.611024 0.203636 11.00000 0.01495 0.01932 = 0.01913 0.00172 0.00359 0.00155 AFIX 43 H18 2 0.388334 0.605289 0.162518 11.00000 -1.20000 AFIX 0 C19 1 0.493867 0.663090 0.305052 11.00000 0.01921 0.01812 = 0.02144 -0.00007 0.00919 0.00379 AFIX 43 H19 2 0.437301 0.694761 0.331686 11.00000 -1.20000 AFIX 0 C20 1 0.605920 0.668916 0.367873 11.00000 0.02180 0.01429 = 0.01608 -0.00188 0.00637 0.00107 AFIX 43 H20 2 0.625914 0.703494 0.437585 11.00000 -1.20000 AFIX 0 C21 1 0.869416 0.735215 0.429484 11.00000 0.02071 0.01723 = 0.01841 -0.00134 0.00365 -0.00203 AFIX 137 H21A 2 0.862634 0.797102 0.372750 11.00000 -1.50000 H21B 2 0.948660 0.718701 0.466619 11.00000 -1.50000 H21C 2 0.833938 0.768559 0.480057 11.00000 -1.50000 AFIX 0 HKLF 4 REM cxy5046_0m_a.res in P2(1)/n REM wR2 = 0.0832, GooF = S = 1.030, Restrained GooF = 1.030 for all data REM R1 = 0.0329 for 3134 Fo > 4sig(Fo) and 0.0362 for all 3434 data REM 238 parameters refined using 0 restraints END WGHT 0.0384 0.7589 REM Instructions for potential hydrogen bonds HTAB C7 O1 EQIV $1 -x+2, -y+1, -z HTAB C9 O3_$1 EQIV $2 -x+2, -y+1, -z+1 HTAB C11 F1_$2 HTAB C17 O2 EQIV $3 -x+1, -y+1, -z HTAB C17 O2_$3 REM Highest difference peak 0.325, deepest hole -0.194, 1-sigma level 0.041 Q1 1 0.8247 0.5584 0.4202 11.00000 0.05 0.32 Q2 1 0.8215 0.5200 0.0929 11.00000 0.05 0.29 Q3 1 0.8346 0.5964 0.3381 11.00000 0.05 0.28 Q4 1 0.8879 0.5677 0.0611 11.00000 0.05 0.28 Q5 1 0.8642 0.4801 0.3162 11.00000 0.05 0.26 ; _shelx_res_checksum 81964 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -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 0.81652(6) 0.32090(8) 0.83386(6) 0.0304(2) Uani 1 1 d . . . . . O1 O 0.91423(7) 0.72011(8) 0.11707(6) 0.02015(19) Uani 1 1 d . . . . . O2 O 0.67438(6) 0.53327(7) 0.01738(6) 0.01802(19) Uani 1 1 d . . . . . O3 O 0.93540(8) 0.64351(8) -0.03365(7) 0.0246(2) Uani 1 1 d . . . . . N1 N 0.75471(7) 0.54139(9) 0.19693(7) 0.0148(2) Uani 1 1 d . . . . . C1 C 0.82458(10) 0.36228(12) 0.73877(9) 0.0218(3) Uani 1 1 d . . . . . C2 C 0.83632(10) 0.27420(11) 0.66644(9) 0.0212(3) Uani 1 1 d . . . . . H2 H 0.839565 0.186555 0.682331 0.025 Uiso 1 1 calc R U . . . C3 C 0.84326(9) 0.31726(11) 0.56969(9) 0.0183(2) Uani 1 1 d . . . . . H3 H 0.851400 0.258126 0.518656 0.022 Uiso 1 1 calc R U . . . C4 C 0.83847(9) 0.44634(11) 0.54595(9) 0.0162(2) Uani 1 1 d . . . . . C5 C 0.84442(9) 0.48774(10) 0.44235(9) 0.0155(2) Uani 1 1 d . . . . . C6 C 0.87411(9) 0.43150(11) 0.36424(9) 0.0173(2) Uani 1 1 d . . . . . H6 H 0.899339 0.348745 0.356143 0.021 Uiso 1 1 calc R U . . . C7 C 0.85294(9) 0.54716(10) 0.29393(8) 0.0154(2) Uani 1 1 d . . . . . H7 H 0.921371 0.585183 0.283436 0.018 Uiso 1 1 calc R U . . . C8 C 0.75785(9) 0.52714(10) 0.09588(8) 0.0144(2) Uani 1 1 d . . . . . C9 C 0.87103(9) 0.50578(10) 0.08030(9) 0.0166(2) Uani 1 1 d . . . . . H9A H 0.925541 0.476087 0.147648 0.020 Uiso 1 1 calc R U . . . H9B H 0.864542 0.440391 0.025222 0.020 Uiso 1 1 calc R U . . . C10 C 0.91098(9) 0.62864(11) 0.04616(9) 0.0163(2) Uani 1 1 d . . . . . C11 C 0.94849(10) 0.84373(11) 0.09234(10) 0.0234(3) Uani 1 1 d . . . . . H11A H 1.025283 0.839396 0.089709 0.035 Uiso 1 1 calc R U . . . H11B H 0.944942 0.903893 0.147446 0.035 Uiso 1 1 calc R U . . . H11C H 0.898441 0.871567 0.023123 0.035 Uiso 1 1 calc R U . . . C12 C 0.82089(10) 0.49045(12) 0.72013(9) 0.0233(3) Uani 1 1 d . . . . . H12 H 0.814260 0.548656 0.772428 0.028 Uiso 1 1 calc R U . . . C13 C 0.82716(10) 0.53213(11) 0.62226(9) 0.0201(2) Uani 1 1 d . . . . . H13 H 0.823698 0.619988 0.607183 0.024 Uiso 1 1 calc R U . . . C14 C 0.81210(9) 0.61322(10) 0.38148(8) 0.0151(2) Uani 1 1 d . . . . . C15 C 0.68768(9) 0.62374(10) 0.32750(9) 0.0150(2) Uani 1 1 d . . . . . C16 C 0.65743(9) 0.57646(10) 0.22344(9) 0.0148(2) Uani 1 1 d . . . . . C17 C 0.54617(9) 0.56695(11) 0.16082(9) 0.0165(2) Uani 1 1 d . . . . . H17 H 0.526064 0.531711 0.091336 0.020 Uiso 1 1 calc R U . . . C18 C 0.46501(9) 0.61102(11) 0.20364(9) 0.0182(2) Uani 1 1 d . . . . . H18 H 0.388334 0.605289 0.162518 0.022 Uiso 1 1 calc R U . . . C19 C 0.49387(10) 0.66309(11) 0.30505(9) 0.0189(2) Uani 1 1 d . . . . . H19 H 0.437301 0.694761 0.331686 0.023 Uiso 1 1 calc R U . . . C20 C 0.60592(10) 0.66892(10) 0.36787(9) 0.0173(2) Uani 1 1 d . . . . . H20 H 0.625914 0.703494 0.437585 0.021 Uiso 1 1 calc R U . . . C21 C 0.86942(10) 0.73522(11) 0.42948(9) 0.0194(2) Uani 1 1 d . . . . . H21A H 0.862634 0.797102 0.372750 0.029 Uiso 1 1 calc R U . . . H21B H 0.948660 0.718701 0.466619 0.029 Uiso 1 1 calc R U . . . H21C H 0.833938 0.768559 0.480057 0.029 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 0.0316(4) 0.0418(5) 0.0218(4) 0.0121(3) 0.0142(3) 0.0073(3) O1 0.0250(4) 0.0164(4) 0.0213(4) -0.0017(3) 0.0105(3) -0.0033(3) O2 0.0189(4) 0.0204(4) 0.0138(4) 0.0001(3) 0.0037(3) -0.0017(3) O3 0.0327(5) 0.0239(4) 0.0233(4) 0.0034(3) 0.0172(4) 0.0016(4) N1 0.0132(4) 0.0172(5) 0.0137(5) 0.0000(3) 0.0040(4) 0.0006(3) C1 0.0169(5) 0.0329(7) 0.0163(6) 0.0076(5) 0.0061(4) 0.0025(5) C2 0.0180(5) 0.0214(6) 0.0231(6) 0.0049(5) 0.0051(5) -0.0005(4) C3 0.0155(5) 0.0191(6) 0.0190(5) -0.0010(4) 0.0038(4) -0.0011(4) C4 0.0122(5) 0.0195(6) 0.0151(5) 0.0001(4) 0.0018(4) -0.0003(4) C5 0.0125(5) 0.0157(5) 0.0162(5) -0.0005(4) 0.0015(4) -0.0006(4) C6 0.0159(5) 0.0181(5) 0.0158(5) -0.0006(4) 0.0019(4) 0.0025(4) C7 0.0143(5) 0.0179(5) 0.0132(5) -0.0009(4) 0.0034(4) -0.0001(4) C8 0.0179(5) 0.0106(5) 0.0153(5) 0.0003(4) 0.0059(4) -0.0013(4) C9 0.0196(6) 0.0154(5) 0.0162(5) -0.0001(4) 0.0076(4) 0.0013(4) C10 0.0135(5) 0.0182(5) 0.0175(5) 0.0010(4) 0.0053(4) 0.0025(4) C11 0.0235(6) 0.0156(6) 0.0320(7) 0.0007(5) 0.0100(5) -0.0025(5) C12 0.0238(6) 0.0290(7) 0.0175(6) -0.0007(5) 0.0071(5) 0.0052(5) C13 0.0217(6) 0.0195(6) 0.0187(6) 0.0004(4) 0.0057(5) 0.0030(4) C14 0.0162(5) 0.0147(5) 0.0141(5) -0.0004(4) 0.0044(4) 0.0003(4) C15 0.0168(5) 0.0124(5) 0.0152(5) 0.0008(4) 0.0040(4) -0.0005(4) C16 0.0168(5) 0.0126(5) 0.0159(5) 0.0008(4) 0.0066(4) 0.0009(4) C17 0.0175(5) 0.0170(5) 0.0143(5) 0.0001(4) 0.0038(4) 0.0001(4) C18 0.0149(5) 0.0193(6) 0.0191(6) 0.0017(4) 0.0036(4) 0.0015(4) C19 0.0192(6) 0.0181(6) 0.0214(6) -0.0001(4) 0.0092(5) 0.0038(4) C20 0.0218(6) 0.0143(5) 0.0161(5) -0.0019(4) 0.0064(4) 0.0011(4) C21 0.0207(6) 0.0172(6) 0.0184(5) -0.0013(4) 0.0037(4) -0.0020(4) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0583 0.0400 '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 C10 O1 C11 116.18(9) . . ? C8 N1 C7 125.73(9) . . ? C8 N1 C16 124.34(9) . . ? C16 N1 C7 108.99(8) . . ? F1 C1 C2 118.55(11) . . ? F1 C1 C12 118.22(11) . . ? C2 C1 C12 123.23(11) . . ? C1 C2 H2 121.0 . . ? C1 C2 C3 118.04(11) . . ? C3 C2 H2 121.0 . . ? C2 C3 H3 119.4 . . ? C2 C3 C4 121.15(11) . . ? C4 C3 H3 119.4 . . ? C3 C4 C5 119.44(10) . . ? C13 C4 C3 118.66(10) . . ? C13 C4 C5 121.90(10) . . ? C4 C5 C14 131.69(10) . . ? C6 C5 C4 134.12(11) . . ? C6 C5 C14 94.13(9) . . ? C5 C6 H6 132.8 . . ? C5 C6 C7 94.37(9) . . ? C7 C6 H6 132.8 . . ? N1 C7 C6 116.03(9) . . ? N1 C7 H7 114.8 . . ? N1 C7 C14 106.24(8) . . ? C6 C7 H7 114.8 . . ? C6 C7 C14 86.70(8) . . ? C14 C7 H7 114.8 . . ? O2 C8 N1 123.07(10) . . ? O2 C8 C9 118.96(9) . . ? N1 C8 C9 117.95(9) . . ? C8 C9 H9A 109.9 . . ? C8 C9 H9B 109.9 . . ? H9A C9 H9B 108.3 . . ? C10 C9 C8 109.04(9) . . ? C10 C9 H9A 109.9 . . ? C10 C9 H9B 109.9 . . ? O1 C10 C9 110.63(9) . . ? O3 C10 O1 124.15(11) . . ? O3 C10 C9 125.22(10) . . ? O1 C11 H11A 109.5 . . ? O1 C11 H11B 109.5 . . ? O1 C11 H11C 109.5 . . ? H11A C11 H11B 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C1 C12 H12 121.0 . . ? C1 C12 C13 118.02(11) . . ? C13 C12 H12 121.0 . . ? C4 C13 H13 119.6 . . ? C12 C13 C4 120.89(11) . . ? C12 C13 H13 119.6 . . ? C5 C14 C7 84.68(8) . . ? C15 C14 C5 112.07(9) . . ? C15 C14 C7 102.47(8) . . ? C15 C14 C21 114.95(9) . . ? C21 C14 C5 120.17(9) . . ? C21 C14 C7 117.66(9) . . ? C16 C15 C14 111.11(9) . . ? C20 C15 C14 129.08(10) . . ? C20 C15 C16 119.79(10) . . ? C15 C16 N1 110.22(9) . . ? C17 C16 N1 128.19(10) . . ? C17 C16 C15 121.58(10) . . ? C16 C17 H17 121.2 . . ? C16 C17 C18 117.64(10) . . ? C18 C17 H17 121.2 . . ? C17 C18 H18 119.3 . . ? C19 C18 C17 121.47(10) . . ? C19 C18 H18 119.3 . . ? C18 C19 H19 120.0 . . ? C18 C19 C20 120.08(10) . . ? C20 C19 H19 120.0 . . ? C15 C20 C19 119.34(10) . . ? C15 C20 H20 120.3 . . ? C19 C20 H20 120.3 . . ? C14 C21 H21A 109.5 . . ? C14 C21 H21B 109.5 . . ? C14 C21 H21C 109.5 . . ? H21A C21 H21B 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 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 C1 1.3661(13) . ? O1 C10 1.3405(14) . ? O1 C11 1.4482(14) . ? O2 C8 1.2257(13) . ? O3 C10 1.1996(14) . ? N1 C7 1.4779(14) . ? N1 C8 1.3586(14) . ? N1 C16 1.4259(14) . ? C1 C2 1.3775(18) . ? C1 C12 1.3781(18) . ? C2 H2 0.9500 . ? C2 C3 1.3875(16) . ? C3 H3 0.9500 . ? C3 C4 1.4001(16) . ? C4 C5 1.4635(15) . ? C4 C13 1.3987(16) . ? C5 C6 1.3440(16) . ? C5 C14 1.5412(15) . ? C6 H6 0.9500 . ? C6 C7 1.5106(15) . ? C7 H7 1.0000 . ? C7 C14 1.5721(14) . ? C8 C9 1.5205(15) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C9 C10 1.5146(15) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12 0.9500 . ? C12 C13 1.3938(16) . ? C13 H13 0.9500 . ? C14 C15 1.5086(15) . ? C14 C21 1.5188(15) . ? C15 C16 1.4009(15) . ? C15 C20 1.3861(16) . ? C16 C17 1.3898(15) . ? C17 H17 0.9500 . ? C17 C18 1.3959(16) . ? C18 H18 0.9500 . ? C18 C19 1.3895(16) . ? C19 H19 0.9500 . ? C19 C20 1.3964(16) . ? C20 H20 0.9500 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag F1 C1 C2 C3 179.34(10) . . . . ? F1 C1 C12 C13 -178.89(10) . . . . ? O2 C8 C9 C10 77.48(12) . . . . ? N1 C7 C14 C5 118.47(9) . . . . ? N1 C7 C14 C15 7.01(11) . . . . ? N1 C7 C14 C21 -120.13(10) . . . . ? N1 C8 C9 C10 -101.07(11) . . . . ? N1 C16 C17 C18 -178.31(10) . . . . ? C1 C2 C3 C4 -0.02(17) . . . . ? C1 C12 C13 C4 -0.90(18) . . . . ? C2 C1 C12 C13 1.31(19) . . . . ? C2 C3 C4 C5 -179.09(10) . . . . ? C2 C3 C4 C13 0.38(17) . . . . ? C3 C4 C5 C6 -14.47(19) . . . . ? C3 C4 C5 C14 161.96(11) . . . . ? C3 C4 C13 C12 0.09(17) . . . . ? C4 C5 C6 C7 -179.99(12) . . . . ? C4 C5 C14 C7 179.98(12) . . . . ? C4 C5 C14 C15 -78.69(14) . . . . ? C4 C5 C14 C21 60.96(16) . . . . ? C5 C4 C13 C12 179.55(11) . . . . ? C5 C6 C7 N1 -109.11(10) . . . . ? C5 C6 C7 C14 -2.63(9) . . . . ? C5 C14 C15 C16 -91.03(11) . . . . ? C5 C14 C15 C20 87.27(14) . . . . ? C6 C5 C14 C7 -2.59(8) . . . . ? C6 C5 C14 C15 98.74(10) . . . . ? C6 C5 C14 C21 -121.61(11) . . . . ? C6 C7 C14 C5 2.30(8) . . . . ? C6 C7 C14 C15 -109.16(9) . . . . ? C6 C7 C14 C21 123.70(10) . . . . ? C7 N1 C8 O2 -173.83(10) . . . . ? C7 N1 C8 C9 4.66(15) . . . . ? C7 N1 C16 C15 9.23(12) . . . . ? C7 N1 C16 C17 -170.02(11) . . . . ? C7 C14 C15 C16 -1.76(11) . . . . ? C7 C14 C15 C20 176.54(11) . . . . ? C8 N1 C7 C6 -106.38(12) . . . . ? C8 N1 C7 C14 159.29(10) . . . . ? C8 N1 C16 C15 -160.25(10) . . . . ? C8 N1 C16 C17 20.50(17) . . . . ? C8 C9 C10 O1 56.07(12) . . . . ? C8 C9 C10 O3 -123.18(12) . . . . ? C11 O1 C10 O3 0.77(16) . . . . ? C11 O1 C10 C9 -178.49(9) . . . . ? C12 C1 C2 C3 -0.86(18) . . . . ? C13 C4 C5 C6 166.07(12) . . . . ? C13 C4 C5 C14 -17.50(18) . . . . ? C14 C5 C6 C7 2.69(9) . . . . ? C14 C15 C16 N1 -4.46(12) . . . . ? C14 C15 C16 C17 174.84(10) . . . . ? C14 C15 C20 C19 -176.26(11) . . . . ? C15 C16 C17 C18 2.52(16) . . . . ? C16 N1 C7 C6 84.33(11) . . . . ? C16 N1 C7 C14 -10.01(11) . . . . ? C16 N1 C8 O2 -6.11(17) . . . . ? C16 N1 C8 C9 172.38(9) . . . . ? C16 C15 C20 C19 1.91(16) . . . . ? C16 C17 C18 C19 0.24(17) . . . . ? C17 C18 C19 C20 -1.88(17) . . . . ? C18 C19 C20 C15 0.78(17) . . . . ? C20 C15 C16 N1 177.06(10) . . . . ? C20 C15 C16 C17 -3.64(17) . . . . ? C21 C14 C15 C16 127.09(10) . . . . ? C21 C14 C15 C20 -54.61(15) . . . . ?