#------------------------------------------------------------------------------ #$Date: 2024-01-06 10:22:26 +0200 (Sat, 06 Jan 2024) $ #$Revision: 288818 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/77/7247726.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_7247726 loop_ _publ_author_name 'Pan, Dongping' 'Liu, Fu-Xiaomin' 'Zeng, Zhongyi' 'Ye, Junwei' 'Cai, Ying' 'Wang, Shengdong' 'Zhou, Zhi' 'Yi, Wei' _publ_section_title ; Practical conversion of gem-difluorocyclopropenes for the chemodivergent assembly of fluorinated heterocyclic frameworks ; _journal_issue 24 _journal_name_full 'Green Chemistry' _journal_page_first 10630 _journal_page_last 10637 _journal_paper_doi 10.1039/D3GC03203E _journal_volume 25 _journal_year 2023 _chemical_formula_moiety 'C17 H15 F N2 O2' _chemical_formula_sum 'C17 H15 F N2 O2' _chemical_formula_weight 298.31 _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 dual _audit_creation_date 2023-03-30 _audit_creation_method ; Olex2 1.5-beta (compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439) ; _audit_update_record ; 2023-07-07 deposited with the CCDC. 2023-11-14 downloaded from the CCDC. ; _cell_angle_alpha 67.050(6) _cell_angle_beta 88.220(4) _cell_angle_gamma 71.172(5) _cell_formula_units_Z 2 _cell_length_a 8.8203(5) _cell_length_b 9.1068(6) _cell_length_c 10.6468(6) _cell_measurement_reflns_used 3642 _cell_measurement_temperature 149.99(10) _cell_measurement_theta_max 73.7350 _cell_measurement_theta_min 5.5820 _cell_volume 740.95(9) _computing_cell_refinement 'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)' _computing_molecular_graphics 'Olex2 1.5-beta (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5-beta (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 149.99(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 5.2684 _diffrn_detector_type AtlasS2 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.964 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w 3.00 77.00 1.00 1.00 -- 40.73 -99.00 -90.00 74 2 \w 80.00 122.00 1.00 1.00 -- 107.58-125.00 -30.00 42 3 \w 100.00 126.00 1.00 1.00 -- 107.58 -45.00 60.00 26 4 \w 63.00 118.00 1.00 1.00 -- 107.58 -61.00 150.00 55 5 \w 51.00 108.00 1.00 1.00 -- 107.58 -94.00 150.00 57 6 \w 50.00 81.00 1.00 1.00 -- 40.73-125.00 60.00 31 7 \w 35.00 81.00 1.00 1.00 -- 107.58 -45.00 60.00 46 8 \w 27.00 106.00 1.00 1.00 -- 107.58 -94.00 60.00 79 9 \w 31.00 95.00 1.00 1.00 -- 107.58 -30.00-120.00 64 10 \w 83.00 173.00 1.00 1.00 -- 107.58 30.00-180.00 90 11 \w 93.00 167.00 1.00 1.00 -- 107.58 45.00 -90.00 74 12 \w 150.00 176.00 1.00 1.00 -- 107.58 102.00 63.00 26 13 \w 114.00 178.00 1.00 1.00 -- 107.58 125.00 120.00 64 14 \w 79.00 177.00 1.00 1.00 -- 107.58 61.00-150.00 98 15 \w 2.00 58.00 1.00 1.00 -- 40.73 -99.00-180.00 56 16 \w -115.00 -16.00 1.00 1.00 -- -40.73 -37.00 30.00 99 17 \w -115.00 -17.00 1.00 1.00 -- -40.73 -37.00 -60.00 98 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, AtlasS2' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0367046000 _diffrn_orient_matrix_UB_12 0.0874228000 _diffrn_orient_matrix_UB_13 -0.1478291000 _diffrn_orient_matrix_UB_21 -0.1684671000 _diffrn_orient_matrix_UB_22 0.1361700000 _diffrn_orient_matrix_UB_23 -0.0325529000 _diffrn_orient_matrix_UB_31 0.0687932000 _diffrn_orient_matrix_UB_32 0.1090937000 _diffrn_orient_matrix_UB_33 0.0455397000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0341 _diffrn_reflns_av_unetI/netI 0.0311 _diffrn_reflns_Laue_measured_fraction_full 0.996 _diffrn_reflns_Laue_measured_fraction_max 0.964 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 4658 _diffrn_reflns_point_group_measured_fraction_full 0.996 _diffrn_reflns_point_group_measured_fraction_max 0.964 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 73.778 _diffrn_reflns_theta_min 4.537 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.807 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.36697 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'light colourless' _exptl_crystal_density_diffrn 1.337 _exptl_crystal_description block _exptl_crystal_F_000 312 _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.388 _refine_diff_density_min -0.372 _refine_diff_density_rms 0.085 _refine_ls_extinction_coef 0.064(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2018/3 (Sheldrick 2018)' _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 205 _refine_ls_number_reflns 2887 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.082 _refine_ls_R_factor_all 0.0611 _refine_ls_R_factor_gt 0.0581 _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^)+(0.0971P)^2^+0.2843P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1552 _refine_ls_wR_factor_ref 0.1585 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2684 _reflns_number_total 2887 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3gc03203e2.cif _cod_data_source_block 244 _cod_depositor_comments 'Adding full bibliography for 7247725--7247728.cif.' _cod_database_code 7247726 _shelx_shelxl_version_number 2018/3 _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 Secondary CH2 refined with riding coordinates: C11(H11A,H11B) 2.b Aromatic/amide H refined with riding coordinates: C2(H2A), C3(H3), C4(H4), C5(H5), C6(H6), C14(H14), C15(H15), C16(H16), C17(H17) 2.c Idealised Me refined as rotating group: C12(H12A,H12B,H12C) ; _shelx_res_file ; TITL 244_a.res in P-1 244.res created by SHELXL-2018/3 at 22:03:21 on 30-Mar-2023 REM Old TITL 244 in P-1 #2 REM SHELXT solution in P-1: R1 0.161, Rweak 0.011, Alpha 0.047 REM 0.000 for 0 systematic absences, Orientation as input REM Formula found by SHELXT: C17 N2 O2 F CELL 1.54184 8.8203 9.1068 10.6468 67.05 88.22 71.172 ZERR 2 0.0005 0.0006 0.0006 0.006 0.004 0.005 LATT 1 SFAC C H F N O UNIT 34 30 2 4 4 L.S. 20 PLAN 7 CONF BOND temp -120 list 4 fmap 2 53 MORE -1 BOND $H ACTA REM REM REM WGHT 0.097100 0.284300 EXTI 0.064045 FVAR 1.46763 F1 3 0.647926 0.257936 0.338363 11.00000 0.02460 0.03997 = 0.02731 -0.01564 0.01024 -0.00570 O1 5 0.291772 0.560740 0.352746 11.00000 0.02327 0.03369 = 0.03123 -0.01306 0.01190 -0.00901 O2 5 0.378187 0.693123 -0.051538 11.00000 0.10016 0.04173 = 0.02448 -0.01381 0.01189 0.00844 N1 4 0.372722 0.345791 0.686594 11.00000 0.02306 0.04035 = 0.03090 -0.02111 0.00823 -0.01615 N2 4 0.420649 0.521959 0.171369 11.00000 0.02824 0.02873 = 0.02425 -0.01485 0.00533 -0.00982 H2 2 0.490422 0.449170 0.144108 11.00000 0.03891 C1 1 0.645860 0.069939 0.622223 11.00000 0.02368 0.02934 = 0.02578 -0.01763 0.00448 -0.01088 C2 1 0.611216 -0.061450 0.726724 11.00000 0.02855 0.03254 = 0.03298 -0.01556 0.00361 -0.01458 AFIX 43 H2A 2 0.504572 -0.053785 0.739376 11.00000 -1.20000 AFIX 0 C3 1 0.735107 -0.203989 0.812235 11.00000 0.04813 0.02962 = 0.03683 -0.01158 -0.00178 -0.01329 AFIX 43 H3 2 0.710994 -0.291852 0.881011 11.00000 -1.20000 AFIX 0 C4 1 0.894288 -0.215646 0.795395 11.00000 0.03880 0.03817 = 0.04197 -0.02108 -0.00775 0.00147 AFIX 43 H4 2 0.977013 -0.311063 0.852738 11.00000 -1.20000 AFIX 0 C5 1 0.929690 -0.085019 0.693116 11.00000 0.02210 0.05483 = 0.04284 -0.03034 0.00050 -0.00398 AFIX 43 H5 2 1.036539 -0.092304 0.682225 11.00000 -1.20000 AFIX 0 C6 1 0.806838 0.057033 0.606495 11.00000 0.02399 0.04058 = 0.03035 -0.02046 0.00449 -0.01248 AFIX 43 H6 2 0.831818 0.144131 0.537585 11.00000 -1.20000 AFIX 0 C7 1 0.512288 0.224167 0.533825 11.00000 0.01794 0.02876 = 0.02745 -0.01606 0.00471 -0.01299 C8 1 0.519119 0.313397 0.402153 11.00000 0.01747 0.03115 = 0.02889 -0.01694 0.00753 -0.00997 C9 1 0.398676 0.478041 0.309032 11.00000 0.01967 0.03046 = 0.02643 -0.01402 0.00565 -0.01422 C10 1 0.350603 0.678282 0.064395 11.00000 0.03628 0.03404 = 0.02418 -0.01494 0.00364 -0.00841 C11 1 0.250270 0.826007 0.093212 11.00000 0.03136 0.03105 = 0.02604 -0.01416 0.00394 -0.00673 AFIX 23 H11A 2 0.308287 0.834379 0.164659 11.00000 -1.20000 H11B 2 0.151539 0.807804 0.126723 11.00000 -1.20000 AFIX 0 C12 1 0.208706 0.990660 -0.033128 11.00000 0.05551 0.03414 = 0.03256 -0.01371 0.00712 -0.00673 AFIX 137 H12A 2 0.157609 0.980313 -0.106086 11.00000 -1.50000 H12B 2 0.305438 1.015222 -0.060962 11.00000 -1.50000 H12C 2 0.136731 1.080783 -0.012398 11.00000 -1.50000 AFIX 0 C13 1 0.361766 0.277646 0.598110 11.00000 0.01968 0.02577 = 0.02223 -0.00965 0.00506 -0.01120 C14 1 0.222741 0.254101 0.566249 11.00000 0.02422 0.03262 = 0.02952 -0.01528 0.00525 -0.01561 AFIX 43 H14 2 0.221582 0.201907 0.506795 11.00000 -1.20000 AFIX 0 C15 1 0.085200 0.310088 0.624971 11.00000 0.01962 0.03442 = 0.03587 -0.01110 0.00498 -0.01569 AFIX 43 H15 2 -0.009962 0.295568 0.606151 11.00000 -1.20000 AFIX 0 C16 1 0.092498 0.387697 0.711805 11.00000 0.02299 0.03214 = 0.03599 -0.01388 0.01245 -0.01055 AFIX 43 H16 2 0.001361 0.430543 0.750010 11.00000 -1.20000 AFIX 0 C17 1 0.237956 0.400382 0.740753 11.00000 0.02986 0.04127 = 0.03460 -0.02355 0.01324 -0.01700 AFIX 43 H17 2 0.242698 0.449836 0.801558 11.00000 -1.20000 AFIX 0 HKLF 4 REM 244_a.res in P-1 REM wR2 = 0.1585, GooF = S = 1.082, Restrained GooF = 1.082 for all data REM R1 = 0.0581 for 2684 Fo > 4sig(Fo) and 0.0611 for all 2887 data REM 205 parameters refined using 0 restraints END WGHT 0.0963 0.2736 REM Highest difference peak 0.388, deepest hole -0.372, 1-sigma level 0.085 Q1 1 0.3168 0.6337 -0.0258 11.00000 0.05 0.39 Q2 1 0.3854 0.6080 0.1472 11.00000 0.05 0.34 Q3 1 0.4272 0.5662 -0.0168 11.00000 0.05 0.33 Q4 1 0.6257 0.0235 0.6645 11.00000 0.05 0.32 Q5 1 0.3214 0.4432 0.4668 11.00000 0.05 0.32 Q6 1 0.8173 -0.1975 0.7901 11.00000 0.05 0.29 Q7 1 0.3033 0.7489 0.0836 11.00000 0.05 0.29 ; _shelx_res_checksum 27882 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 11.768 _oxdiff_exptl_absorpt_empirical_full_min 0.530 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 0.64793(12) 0.25794(13) 0.33836(10) 0.0315(3) Uani 1 1 d . . . . . O1 O 0.29177(14) 0.56074(16) 0.35275(13) 0.0298(3) Uani 1 1 d . . . . . O2 O 0.3782(3) 0.6931(2) -0.05154(15) 0.0640(6) Uani 1 1 d . . . . . N1 N 0.37272(17) 0.3458(2) 0.68659(15) 0.0279(4) Uani 1 1 d . . . . . N2 N 0.42065(18) 0.52196(18) 0.17137(14) 0.0257(4) Uani 1 1 d . . . . . H2 H 0.490(3) 0.449(3) 0.144(2) 0.039(6) Uiso 1 1 d . . . . . C1 C 0.64586(19) 0.0699(2) 0.62222(17) 0.0236(4) Uani 1 1 d . . . . . C2 C 0.6112(2) -0.0614(2) 0.72672(19) 0.0295(4) Uani 1 1 d . . . . . H2A H 0.504572 -0.053785 0.739376 0.035 Uiso 1 1 calc R U . . . C3 C 0.7351(3) -0.2040(2) 0.8122(2) 0.0386(5) Uani 1 1 d . . . . . H3 H 0.710994 -0.291852 0.881011 0.046 Uiso 1 1 calc R U . . . C4 C 0.8943(3) -0.2156(3) 0.7954(2) 0.0415(5) Uani 1 1 d . . . . . H4 H 0.977013 -0.311063 0.852738 0.050 Uiso 1 1 calc R U . . . C5 C 0.9297(2) -0.0850(3) 0.6931(2) 0.0387(5) Uani 1 1 d . . . . . H5 H 1.036539 -0.092304 0.682225 0.046 Uiso 1 1 calc R U . . . C6 C 0.8068(2) 0.0570(2) 0.60650(18) 0.0292(4) Uani 1 1 d . . . . . H6 H 0.831818 0.144131 0.537585 0.035 Uiso 1 1 calc R U . . . C7 C 0.51229(18) 0.2242(2) 0.53383(16) 0.0219(4) Uani 1 1 d . . . . . C8 C 0.51912(19) 0.3134(2) 0.40215(17) 0.0239(4) Uani 1 1 d . . . . . C9 C 0.39868(19) 0.4780(2) 0.30903(17) 0.0232(4) Uani 1 1 d . . . . . C10 C 0.3506(2) 0.6783(2) 0.06440(18) 0.0314(4) Uani 1 1 d . . . . . C11 C 0.2503(2) 0.8260(2) 0.09321(18) 0.0296(4) Uani 1 1 d . . . . . H11A H 0.308287 0.834379 0.164659 0.036 Uiso 1 1 calc R U . . . H11B H 0.151539 0.807804 0.126723 0.036 Uiso 1 1 calc R U . . . C12 C 0.2087(3) 0.9907(3) -0.0331(2) 0.0429(5) Uani 1 1 d . . . . . H12A H 0.157609 0.980313 -0.106086 0.064 Uiso 1 1 calc R U . . . H12B H 0.305438 1.015222 -0.060962 0.064 Uiso 1 1 calc R U . . . H12C H 0.136731 1.080783 -0.012398 0.064 Uiso 1 1 calc R U . . . C13 C 0.36177(19) 0.2776(2) 0.59811(16) 0.0217(4) Uani 1 1 d . . . . . C14 C 0.2227(2) 0.2541(2) 0.56625(18) 0.0263(4) Uani 1 1 d . . . . . H14 H 0.221582 0.201907 0.506795 0.032 Uiso 1 1 calc R U . . . C15 C 0.0852(2) 0.3101(2) 0.62497(19) 0.0293(4) Uani 1 1 d . . . . . H15 H -0.009962 0.295568 0.606151 0.035 Uiso 1 1 calc R U . . . C16 C 0.0925(2) 0.3877(2) 0.71180(19) 0.0302(4) Uani 1 1 d . . . . . H16 H 0.001361 0.430543 0.750010 0.036 Uiso 1 1 calc R U . . . C17 C 0.2380(2) 0.4004(2) 0.74075(19) 0.0314(4) Uani 1 1 d . . . . . H17 H 0.242698 0.449836 0.801558 0.038 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 0.0246(5) 0.0400(6) 0.0273(5) -0.0156(4) 0.0102(4) -0.0057(4) O1 0.0233(6) 0.0337(7) 0.0312(7) -0.0131(5) 0.0119(5) -0.0090(5) O2 0.1002(14) 0.0417(9) 0.0245(8) -0.0138(6) 0.0119(8) 0.0084(9) N1 0.0231(7) 0.0404(8) 0.0309(8) -0.0211(7) 0.0082(6) -0.0161(6) N2 0.0282(8) 0.0287(7) 0.0243(7) -0.0149(6) 0.0053(6) -0.0098(6) C1 0.0237(8) 0.0293(8) 0.0258(8) -0.0176(7) 0.0045(6) -0.0109(7) C2 0.0286(9) 0.0325(9) 0.0330(9) -0.0156(7) 0.0036(7) -0.0146(7) C3 0.0481(12) 0.0296(9) 0.0368(10) -0.0116(8) -0.0018(8) -0.0133(8) C4 0.0388(11) 0.0382(10) 0.0420(11) -0.0211(9) -0.0078(8) 0.0015(8) C5 0.0221(9) 0.0548(12) 0.0428(11) -0.0303(10) 0.0005(7) -0.0040(8) C6 0.0240(9) 0.0406(10) 0.0304(9) -0.0205(7) 0.0045(7) -0.0125(7) C7 0.0179(7) 0.0288(8) 0.0275(8) -0.0161(7) 0.0047(6) -0.0130(6) C8 0.0175(7) 0.0311(9) 0.0289(8) -0.0169(7) 0.0075(6) -0.0100(6) C9 0.0197(8) 0.0305(8) 0.0264(8) -0.0140(7) 0.0056(6) -0.0142(6) C10 0.0363(10) 0.0340(10) 0.0242(8) -0.0149(7) 0.0036(7) -0.0084(8) C11 0.0314(9) 0.0311(9) 0.0260(8) -0.0142(7) 0.0039(7) -0.0067(7) C12 0.0555(13) 0.0341(10) 0.0326(10) -0.0137(8) 0.0071(9) -0.0067(9) C13 0.0197(8) 0.0258(8) 0.0222(7) -0.0097(6) 0.0051(6) -0.0112(6) C14 0.0242(8) 0.0326(9) 0.0295(8) -0.0153(7) 0.0052(6) -0.0156(7) C15 0.0196(8) 0.0344(9) 0.0359(9) -0.0111(7) 0.0050(7) -0.0157(7) C16 0.0230(8) 0.0321(9) 0.0360(9) -0.0139(7) 0.0125(7) -0.0106(7) C17 0.0299(9) 0.0413(10) 0.0346(9) -0.0236(8) 0.0132(7) -0.0170(8) 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' F F 0.0727 0.0534 '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' 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 C13 N1 C17 116.71(14) . . ? C9 N2 H2 120.5(15) . . ? C10 N2 H2 112.2(16) . . ? C10 N2 C9 127.13(15) . . ? C2 C1 C6 118.85(16) . . ? C2 C1 C7 119.93(15) . . ? C6 C1 C7 121.16(15) . . ? C1 C2 H2A 119.8 . . ? C3 C2 C1 120.39(17) . . ? C3 C2 H2A 119.8 . . ? C2 C3 H3 119.9 . . ? C4 C3 C2 120.25(19) . . ? C4 C3 H3 119.9 . . ? C3 C4 H4 120.1 . . ? C5 C4 C3 119.73(18) . . ? C5 C4 H4 120.1 . . ? C4 C5 H5 119.8 . . ? C4 C5 C6 120.41(18) . . ? C6 C5 H5 119.8 . . ? C1 C6 H6 119.8 . . ? C5 C6 C1 120.36(18) . . ? C5 C6 H6 119.8 . . ? C1 C7 C13 117.35(13) . . ? C8 C7 C1 123.47(14) . . ? C8 C7 C13 119.17(14) . . ? F1 C8 C9 112.57(13) . . ? C7 C8 F1 120.10(15) . . ? C7 C8 C9 127.32(15) . . ? O1 C9 N2 124.57(15) . . ? O1 C9 C8 121.69(15) . . ? N2 C9 C8 113.73(14) . . ? O2 C10 N2 118.52(17) . . ? O2 C10 C11 121.29(17) . . ? N2 C10 C11 120.12(15) . . ? C10 C11 H11A 109.2 . . ? C10 C11 H11B 109.2 . . ? C10 C11 C12 112.07(15) . . ? H11A C11 H11B 107.9 . . ? C12 C11 H11A 109.2 . . ? C12 C11 H11B 109.2 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12B 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N1 C13 C7 115.91(14) . . ? N1 C13 C14 123.54(15) . . ? C14 C13 C7 120.55(14) . . ? C13 C14 H14 120.7 . . ? C13 C14 C15 118.54(15) . . ? C15 C14 H14 120.7 . . ? C14 C15 H15 120.7 . . ? C16 C15 C14 118.63(15) . . ? C16 C15 H15 120.7 . . ? C15 C16 H16 120.7 . . ? C15 C16 C17 118.53(16) . . ? C17 C16 H16 120.7 . . ? N1 C17 C16 123.95(16) . . ? N1 C17 H17 118.0 . . ? C16 C17 H17 118.0 . . ? 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 C8 1.3625(18) . ? O1 C9 1.209(2) . ? O2 C10 1.214(2) . ? N1 C13 1.335(2) . ? N1 C17 1.339(2) . ? N2 H2 0.88(3) . ? N2 C9 1.386(2) . ? N2 C10 1.385(2) . ? C1 C2 1.393(2) . ? C1 C6 1.397(2) . ? C1 C7 1.489(2) . ? C2 H2A 0.9300 . ? C2 C3 1.390(3) . ? C3 H3 0.9300 . ? C3 C4 1.385(3) . ? C4 H4 0.9300 . ? C4 C5 1.381(3) . ? C5 H5 0.9300 . ? C5 C6 1.387(3) . ? C6 H6 0.9300 . ? C7 C8 1.329(2) . ? C7 C13 1.501(2) . ? C8 C9 1.496(2) . ? C10 C11 1.491(2) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C11 C12 1.515(3) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C14 1.385(2) . ? C14 H14 0.9300 . ? C14 C15 1.387(2) . ? C15 H15 0.9300 . ? C15 C16 1.379(3) . ? C16 H16 0.9300 . ? C16 C17 1.379(3) . ? C17 H17 0.9300 . ? 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 C8 C9 O1 -167.00(14) . . . . ? F1 C8 C9 N2 14.22(19) . . . . ? O2 C10 C11 C12 -6.9(3) . . . . ? N1 C13 C14 C15 2.6(3) . . . . ? N2 C10 C11 C12 170.11(18) . . . . ? C1 C2 C3 C4 0.8(3) . . . . ? C1 C7 C8 F1 5.2(2) . . . . ? C1 C7 C8 C9 -173.69(14) . . . . ? C1 C7 C13 N1 72.82(19) . . . . ? C1 C7 C13 C14 -106.52(17) . . . . ? C2 C1 C6 C5 0.5(3) . . . . ? C2 C1 C7 C8 -146.99(17) . . . . ? C2 C1 C7 C13 31.8(2) . . . . ? C2 C3 C4 C5 0.0(3) . . . . ? C3 C4 C5 C6 -0.5(3) . . . . ? C4 C5 C6 C1 0.3(3) . . . . ? C6 C1 C2 C3 -1.0(3) . . . . ? C6 C1 C7 C8 35.9(2) . . . . ? C6 C1 C7 C13 -145.33(15) . . . . ? C7 C1 C2 C3 -178.24(15) . . . . ? C7 C1 C6 C5 177.62(15) . . . . ? C7 C8 C9 O1 11.9(3) . . . . ? C7 C8 C9 N2 -166.85(16) . . . . ? C7 C13 C14 C15 -178.09(15) . . . . ? C8 C7 C13 N1 -108.33(18) . . . . ? C8 C7 C13 C14 72.3(2) . . . . ? C9 N2 C10 O2 -177.1(2) . . . . ? C9 N2 C10 C11 5.9(3) . . . . ? C10 N2 C9 O1 14.7(3) . . . . ? C10 N2 C9 C8 -166.55(16) . . . . ? C13 N1 C17 C16 1.0(3) . . . . ? C13 C7 C8 F1 -173.60(13) . . . . ? C13 C7 C8 C9 7.5(3) . . . . ? C13 C14 C15 C16 0.4(3) . . . . ? C14 C15 C16 C17 -2.5(3) . . . . ? C15 C16 C17 N1 1.9(3) . . . . ? C17 N1 C13 C7 177.42(15) . . . . ? C17 N1 C13 C14 -3.3(3) . . . . ?