#------------------------------------------------------------------------------ #$Date: 2024-01-06 10:22:26 +0200 (Sat, 06 Jan 2024) $ #$Revision: 288818 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/77/7247727.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_7247727 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 H16 F2 N2 O' _chemical_formula_sum 'C17 H16 F2 N2 O' _chemical_formula_weight 302.32 _space_group_crystal_system orthorhombic _space_group_IT_number 43 _space_group_name_Hall 'F 2 -2d' _space_group_name_H-M_alt 'F d d 2' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _audit_creation_date 2022-04-06 _audit_creation_method ; Olex2 1.5-beta (compiled 2021.12.09 svn.r5202d8cf 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 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 16 _cell_length_a 37.7194(4) _cell_length_b 16.9142(2) _cell_length_c 9.49011(12) _cell_measurement_reflns_used 8539 _cell_measurement_temperature 294.60(10) _cell_measurement_theta_max 75.4790 _cell_measurement_theta_min 5.4500 _cell_volume 6054.63(12) _computing_cell_refinement 'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)' _computing_data_collection 'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)' _computing_data_reduction 'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)' _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 2017/1 (Sheldrick, 2015)' _computing_structure_solution 'SHELXS (Sheldrick, 2008)' _diffrn_ambient_environment air _diffrn_ambient_temperature 294.60(10) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 10.0000 _diffrn_detector_type HyPix _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.985 _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 84.00 178.00 0.50 0.80 -- 109.26 26.00 7.00 188 2 \w 80.00 178.00 0.50 0.80 -- 109.26 77.00-120.00 196 3 \w 90.00 118.00 0.50 0.80 -- 109.26 30.00-180.00 56 4 \w 125.00 177.00 0.50 0.80 -- 109.26 30.00-180.00 104 5 \w -27.00 38.00 0.50 0.27 -- -43.18 19.00 120.00 130 6 \w -51.00 -14.00 0.50 0.80 -- -90.25 45.00 120.00 74 7 \w -51.00 -14.00 0.50 0.80 -- -90.25 45.00 0.00 74 8 \w -51.00 -14.00 0.50 0.80 -- -90.25 45.00 30.00 74 9 \w -32.00 36.00 0.50 0.27 -- -43.18 26.00 7.00 136 10 \w 58.00 94.00 0.50 0.80 -- 109.26-103.00 91.00 72 11 \w 36.00 105.00 0.50 0.80 -- 109.26 -94.00 30.00 138 12 \w -86.00 -13.00 0.50 0.27 -- -43.18 125.00-180.00 146 13 \w -81.00 -15.00 0.50 0.80 -- -90.25 103.00-166.00 132 14 \w -82.00 -15.00 0.50 0.80 -- -90.25 112.00 95.00 134 15 \w -36.00 32.00 0.50 0.27 -- 43.18 -26.00-156.00 136 16 \w 35.00 106.00 0.50 0.80 -- 109.26 -77.00-180.00 142 17 \w 35.00 71.00 0.50 0.80 -- 109.26 -61.00 -90.00 72 18 \w 35.00 71.00 0.50 0.80 -- 109.26 -61.00 -30.00 72 19 \w 35.00 106.00 0.50 0.80 -- 109.26 -77.00 120.00 142 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy, Dualflex, HyPix' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0039474000 _diffrn_orient_matrix_UB_12 -0.0584249000 _diffrn_orient_matrix_UB_13 -0.1235441000 _diffrn_orient_matrix_UB_21 -0.0137158000 _diffrn_orient_matrix_UB_22 -0.0674732000 _diffrn_orient_matrix_UB_23 0.0943938000 _diffrn_orient_matrix_UB_31 -0.0382741000 _diffrn_orient_matrix_UB_32 0.0181410000 _diffrn_orient_matrix_UB_33 -0.0466123000 _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 0.0253 _diffrn_reflns_av_unetI/netI 0.0226 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.985 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_h_min -46 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 10107 _diffrn_reflns_point_group_measured_fraction_full 0.947 _diffrn_reflns_point_group_measured_fraction_max 0.915 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 75.506 _diffrn_reflns_theta_min 4.689 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'PhotonJet (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.842 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.59735 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.327 _exptl_crystal_description block _exptl_crystal_F_000 2528 _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.09 _refine_diff_density_max 0.137 _refine_diff_density_min -0.185 _refine_diff_density_rms 0.049 _refine_ls_abs_structure_details ; Flack x determined using 1133 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.02(7) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 200 _refine_ls_number_reflns 2875 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.051 _refine_ls_R_factor_all 0.0335 _refine_ls_R_factor_gt 0.0323 _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^)+(0.0554P)^2^+1.3038P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0859 _refine_ls_wR_factor_ref 0.0871 _reflns_Friedel_coverage 0.749 _reflns_Friedel_fraction_full 0.887 _reflns_Friedel_fraction_max 0.835 _reflns_number_gt 2752 _reflns_number_total 2875 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3gc03203e2.cif _cod_data_source_block pdp-31 _cod_depositor_comments 'Adding full bibliography for 7247725--7247728.cif.' _cod_original_cell_volume 6054.64(13) _cod_database_code 7247727 _shelx_shelxl_version_number 2017/1 _chemical_oxdiff_formula 'C272 H256 N32 O48 ' _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_max 0.928 _shelx_estimated_absorpt_t_min 0.898 _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: C8(H8), C10(H10) 2.b Secondary CH2 refined with riding coordinates: C16(H16A,H16B) 2.c Aromatic/amide H refined with riding coordinates: C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14) 2.d Idealised Me refined as rotating group: C17(H17A,H17B,H17C) ; _shelx_res_file ; TITL 20220406-pdp-31_a.res in Fdd2 pdp-31.res created by SHELXL-2017/1 at 12:58:45 on 06-Apr-2022 REM Old TITL 20220406-pdp-31 in Fdd2 REM SHELXT solution in Fdd2: R1 0.125, Rweak 0.043, Alpha 0.006 REM 0.839 for 79 systematic absences, Orientation as input REM Flack x = -0.098 ( 0.116 ) from 993 Parsons' quotients REM Formula found by SHELXT: C17 N2 O1 CELL 1.54184 37.719399 16.91425 9.490109 90 90 90 ZERR 16 0.000441 0.000202 0.000122 0 0 0 LATT -4 SYMM -X,-Y,+Z SYMM 0.25+X,0.25-Y,0.25+Z SYMM 0.25-X,0.25+Y,0.25+Z SFAC C H F N O UNIT 272 256 32 32 16 L.S. 10 PLAN 5 SIZE 0.09 0.11 0.13 CONF BOND $H MORE -1 fmap 2 acta REM REM REM WGHT 0.055400 1.303800 FVAR 0.17256 F1 3 0.550080 0.553109 0.814585 11.00000 0.12503 0.06105 = 0.04446 0.01054 0.02203 0.00220 F2 3 0.578459 0.660852 0.758733 11.00000 0.09486 0.05261 = 0.05496 -0.01357 -0.01187 -0.00524 O1 5 0.509942 0.753902 0.647518 11.00000 0.06398 0.04769 = 0.06270 -0.00652 0.01814 0.00641 N1 4 0.569352 0.668300 0.402616 11.00000 0.04312 0.03937 = 0.04120 0.00440 0.00668 0.00753 N2 4 0.541130 0.678464 0.500708 11.00000 0.04604 0.03816 = 0.04644 0.00129 0.00981 0.00558 C1 1 0.571377 0.473368 0.552031 11.00000 0.04713 0.03607 = 0.04129 0.00090 0.00729 -0.00232 C2 1 0.591136 0.425259 0.639706 11.00000 0.07230 0.04549 = 0.05057 0.00182 -0.00793 0.00560 AFIX 43 H2 2 0.603852 0.447274 0.713931 11.00000 -1.20000 AFIX 0 C3 1 0.592064 0.344025 0.617294 11.00000 0.09187 0.04506 = 0.06333 0.00974 0.00096 0.01390 AFIX 43 H3 2 0.605423 0.311886 0.676482 11.00000 -1.20000 AFIX 0 C4 1 0.573213 0.310989 0.507446 11.00000 0.08866 0.03491 = 0.06458 -0.00299 0.01633 -0.00099 AFIX 43 H4 2 0.573895 0.256655 0.492680 11.00000 -1.20000 AFIX 0 C5 1 0.553540 0.358071 0.420339 11.00000 0.07363 0.04819 = 0.06014 -0.01200 0.00485 -0.01226 AFIX 43 H5 2 0.540734 0.335724 0.346676 11.00000 -1.20000 AFIX 0 C6 1 0.552664 0.439453 0.441837 11.00000 0.05599 0.04470 = 0.05049 -0.00179 -0.00308 -0.00366 AFIX 43 H6 2 0.539418 0.471320 0.381788 11.00000 -1.20000 AFIX 0 C7 1 0.571082 0.561136 0.571324 11.00000 0.04565 0.03588 = 0.03807 0.00176 -0.00039 -0.00124 C8 1 0.536545 0.608368 0.585380 11.00000 0.04723 0.03687 = 0.04622 -0.00030 0.01096 -0.00176 AFIX 13 H8 2 0.513752 0.580563 0.584395 11.00000 -1.20000 AFIX 0 C9 1 0.560579 0.598561 0.706069 11.00000 0.07434 0.03917 = 0.03879 -0.00049 0.00402 -0.00435 C10 1 0.594829 0.615657 0.475770 11.00000 0.03928 0.03734 = 0.04612 0.00534 -0.00070 -0.00079 AFIX 13 H10 2 0.609920 0.648059 0.536850 11.00000 -1.20000 AFIX 0 C11 1 0.618026 0.571638 0.374746 11.00000 0.04234 0.04922 = 0.06441 0.01182 0.01099 0.00955 AFIX 43 H11 2 0.638992 0.549257 0.407426 11.00000 -1.20000 AFIX 0 C12 1 0.609568 0.563703 0.240698 11.00000 0.06510 0.05297 = 0.05655 0.00573 0.02314 0.01717 AFIX 43 H12 2 0.624536 0.535852 0.180695 11.00000 -1.20000 AFIX 0 C13 1 0.577281 0.597860 0.186217 11.00000 0.07789 0.05968 = 0.04075 0.00074 0.00529 0.01536 AFIX 43 H13 2 0.570141 0.587244 0.094347 11.00000 -1.20000 AFIX 0 C14 1 0.557763 0.644688 0.268305 11.00000 0.05608 0.05086 = 0.04133 0.00574 -0.00001 0.01224 AFIX 43 H14 2 0.535872 0.662225 0.235814 11.00000 -1.20000 AFIX 0 C15 1 0.528824 0.750626 0.543165 11.00000 0.04247 0.04030 = 0.04823 -0.00422 0.00107 0.00434 C16 1 0.537692 0.820137 0.451435 11.00000 0.06394 0.04599 = 0.05818 0.00594 0.00418 0.00815 AFIX 23 H16A 2 0.562957 0.819999 0.432377 11.00000 -1.20000 H16B 2 0.525430 0.814626 0.362129 11.00000 -1.20000 AFIX 0 C17 1 0.527767 0.897474 0.516399 11.00000 0.16359 0.04264 = 0.09755 0.01170 0.03497 0.01840 AFIX 137 H17A 2 0.530306 0.938826 0.447847 11.00000 -1.50000 H17B 2 0.543017 0.907974 0.595196 11.00000 -1.50000 H17C 2 0.503601 0.895325 0.547903 11.00000 -1.50000 AFIX 0 HKLF 4 REM 20220406-pdp-31_a.res in Fdd2 REM R1 = 0.0323 for 2752 Fo > 4sig(Fo) and 0.0335 for all 2875 data REM 200 parameters refined using 1 restraints END WGHT 0.0554 1.3039 REM Highest difference peak 0.137, deepest hole -0.185, 1-sigma level 0.049 Q1 1 0.5084 0.8704 0.4425 11.00000 0.05 0.14 Q2 1 0.4950 0.8586 0.3871 11.00000 0.05 0.13 Q3 1 0.6261 0.3660 0.7870 11.00000 0.05 0.12 Q4 1 0.6245 0.3162 0.6890 11.00000 0.05 0.12 Q5 1 0.6260 0.5739 0.0696 11.00000 0.05 0.12 ; _shelx_res_checksum 16719 _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 1.515 _oxdiff_exptl_absorpt_empirical_full_min 0.579 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, z' 'x+1/4, -y+1/4, z+1/4' '-x+1/4, y+1/4, z+1/4' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/4, -y+3/4, z+3/4' '-x+1/4, y+3/4, z+3/4' 'x+1/2, y, z+1/2' '-x+1/2, -y, z+1/2' 'x+3/4, -y+1/4, z+3/4' '-x+3/4, y+1/4, z+3/4' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' 'x+3/4, -y+3/4, z+1/4' '-x+3/4, y+3/4, z+1/4' 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 0.55008(5) 0.55311(9) 0.81458(16) 0.0768(5) Uani 1 1 d . . . . . F2 F 0.57846(4) 0.66085(8) 0.75873(17) 0.0675(4) Uani 1 1 d . . . . . O1 O 0.50994(4) 0.75390(9) 0.6475(2) 0.0581(4) Uani 1 1 d . . . . . N1 N 0.56935(4) 0.66830(9) 0.40262(18) 0.0412(3) Uani 1 1 d . . . . . N2 N 0.54113(4) 0.67846(9) 0.50071(19) 0.0435(4) Uani 1 1 d . . . . . C1 C 0.57138(5) 0.47337(11) 0.5520(2) 0.0415(4) Uani 1 1 d . . . . . C2 C 0.59114(6) 0.42526(13) 0.6397(3) 0.0561(5) Uani 1 1 d . . . . . H2 H 0.603852 0.447274 0.713931 0.067 Uiso 1 1 calc R U . . . C3 C 0.59206(8) 0.34402(14) 0.6173(3) 0.0668(7) Uani 1 1 d . . . . . H3 H 0.605423 0.311886 0.676482 0.080 Uiso 1 1 calc R U . . . C4 C 0.57321(7) 0.31099(13) 0.5074(3) 0.0627(6) Uani 1 1 d . . . . . H4 H 0.573895 0.256655 0.492680 0.075 Uiso 1 1 calc R U . . . C5 C 0.55354(7) 0.35807(14) 0.4203(3) 0.0607(6) Uani 1 1 d . . . . . H5 H 0.540734 0.335724 0.346676 0.073 Uiso 1 1 calc R U . . . C6 C 0.55266(6) 0.43945(12) 0.4418(2) 0.0504(5) Uani 1 1 d . . . . . H6 H 0.539418 0.471320 0.381788 0.060 Uiso 1 1 calc R U . . . C7 C 0.57108(5) 0.56114(10) 0.5713(2) 0.0399(4) Uani 1 1 d . . . . . C8 C 0.53655(5) 0.60837(10) 0.5854(2) 0.0434(4) Uani 1 1 d . . . . . H8 H 0.513752 0.580563 0.584395 0.052 Uiso 1 1 calc R U . . . C9 C 0.56058(6) 0.59856(11) 0.7061(2) 0.0508(5) Uani 1 1 d . . . . . C10 C 0.59483(5) 0.61566(11) 0.4758(2) 0.0409(4) Uani 1 1 d . . . . . H10 H 0.609920 0.648059 0.536850 0.049 Uiso 1 1 calc R U . . . C11 C 0.61803(5) 0.57164(12) 0.3747(3) 0.0520(5) Uani 1 1 d . . . . . H11 H 0.638992 0.549257 0.407426 0.062 Uiso 1 1 calc R U . . . C12 C 0.60957(6) 0.56370(13) 0.2407(3) 0.0582(6) Uani 1 1 d . . . . . H12 H 0.624536 0.535852 0.180695 0.070 Uiso 1 1 calc R U . . . C13 C 0.57728(7) 0.59786(14) 0.1862(3) 0.0594(6) Uani 1 1 d . . . . . H13 H 0.570141 0.587244 0.094347 0.071 Uiso 1 1 calc R U . . . C14 C 0.55776(5) 0.64469(12) 0.2683(2) 0.0494(5) Uani 1 1 d . . . . . H14 H 0.535872 0.662225 0.235814 0.059 Uiso 1 1 calc R U . . . C15 C 0.52882(5) 0.75063(11) 0.5432(2) 0.0437(4) Uani 1 1 d . . . . . C16 C 0.53769(6) 0.82014(12) 0.4514(3) 0.0560(5) Uani 1 1 d . . . . . H16A H 0.562957 0.819999 0.432377 0.067 Uiso 1 1 calc R U . . . H16B H 0.525430 0.814626 0.362129 0.067 Uiso 1 1 calc R U . . . C17 C 0.52777(12) 0.89747(16) 0.5164(5) 0.1013(13) Uani 1 1 d . . . . . H17A H 0.530306 0.938826 0.447847 0.152 Uiso 1 1 calc R U . . . H17B H 0.543017 0.907974 0.595196 0.152 Uiso 1 1 calc R U . . . H17C H 0.503601 0.895325 0.547903 0.152 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 0.1250(13) 0.0610(8) 0.0445(8) 0.0105(6) 0.0220(8) 0.0022(8) F2 0.0949(10) 0.0526(7) 0.0550(8) -0.0136(6) -0.0119(7) -0.0052(7) O1 0.0640(9) 0.0477(7) 0.0627(10) -0.0065(7) 0.0181(8) 0.0064(6) N1 0.0431(7) 0.0394(8) 0.0412(8) 0.0044(6) 0.0067(6) 0.0075(6) N2 0.0460(8) 0.0382(7) 0.0464(9) 0.0013(6) 0.0098(7) 0.0056(6) C1 0.0471(8) 0.0361(8) 0.0413(10) 0.0009(7) 0.0073(8) -0.0023(7) C2 0.0723(13) 0.0455(11) 0.0506(12) 0.0018(9) -0.0079(10) 0.0056(9) C3 0.0919(17) 0.0451(11) 0.0633(16) 0.0097(10) 0.0010(13) 0.0139(10) C4 0.0887(15) 0.0349(9) 0.0646(15) -0.0030(9) 0.0163(13) -0.0010(9) C5 0.0736(14) 0.0482(11) 0.0601(14) -0.0120(10) 0.0048(11) -0.0123(10) C6 0.0560(11) 0.0447(10) 0.0505(12) -0.0018(9) -0.0031(9) -0.0037(8) C7 0.0457(8) 0.0359(8) 0.0381(9) 0.0018(7) -0.0004(7) -0.0012(7) C8 0.0472(9) 0.0369(8) 0.0462(10) -0.0003(7) 0.0110(8) -0.0018(7) C9 0.0743(12) 0.0392(9) 0.0388(10) -0.0005(8) 0.0040(9) -0.0044(9) C10 0.0393(8) 0.0373(8) 0.0461(10) 0.0053(7) -0.0007(7) -0.0008(7) C11 0.0423(9) 0.0492(11) 0.0644(14) 0.0118(10) 0.0110(9) 0.0095(7) C12 0.0651(12) 0.0530(11) 0.0566(13) 0.0057(10) 0.0231(11) 0.0172(9) C13 0.0779(14) 0.0597(13) 0.0407(11) 0.0007(9) 0.0053(10) 0.0154(11) C14 0.0561(10) 0.0509(10) 0.0413(10) 0.0057(8) 0.0000(8) 0.0122(8) C15 0.0425(8) 0.0403(9) 0.0482(10) -0.0042(7) 0.0011(8) 0.0043(7) C16 0.0639(12) 0.0460(11) 0.0582(13) 0.0059(9) 0.0042(10) 0.0082(9) C17 0.164(4) 0.0426(13) 0.098(3) 0.0117(14) 0.035(3) 0.0184(16) 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 N2 N1 C10 104.53(14) . . ? C14 N1 N2 113.24(15) . . ? C14 N1 C10 117.10(15) . . ? N1 N2 C8 110.76(14) . . ? C15 N2 N1 123.66(15) . . ? C15 N2 C8 121.94(17) . . ? C2 C1 C6 119.03(18) . . ? C2 C1 C7 120.98(18) . . ? C6 C1 C7 119.96(17) . . ? C1 C2 H2 119.9 . . ? C1 C2 C3 120.2(2) . . ? C3 C2 H2 119.9 . . ? C2 C3 H3 119.9 . . ? C4 C3 C2 120.2(2) . . ? C4 C3 H3 119.9 . . ? C3 C4 H4 120.0 . . ? C5 C4 C3 120.0(2) . . ? C5 C4 H4 120.0 . . ? C4 C5 H5 120.0 . . ? C4 C5 C6 120.0(2) . . ? C6 C5 H5 120.0 . . ? C1 C6 C5 120.5(2) . . ? C1 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? C1 C7 C8 122.27(15) . . ? C1 C7 C10 120.46(16) . . ? C8 C7 C10 103.20(14) . . ? C9 C7 C1 122.14(17) . . ? C9 C7 C8 58.34(14) . . ? C9 C7 C10 113.55(15) . . ? N2 C8 C7 106.13(14) . . ? N2 C8 H8 119.6 . . ? N2 C8 C9 116.92(16) . . ? C7 C8 H8 119.6 . . ? C9 C8 C7 59.02(13) . . ? C9 C8 H8 119.6 . . ? F1 C9 F2 108.09(18) . . ? F1 C9 C7 119.72(17) . . ? F1 C9 C8 118.66(19) . . ? F2 C9 C7 121.38(19) . . ? F2 C9 C8 120.63(17) . . ? C8 C9 C7 62.64(13) . . ? N1 C10 C7 104.65(14) . . ? N1 C10 H10 108.5 . . ? N1 C10 C11 112.20(17) . . ? C7 C10 H10 108.5 . . ? C11 C10 C7 114.24(15) . . ? C11 C10 H10 108.5 . . ? C10 C11 H11 119.1 . . ? C12 C11 C10 121.83(19) . . ? C12 C11 H11 119.1 . . ? C11 C12 H12 119.7 . . ? C11 C12 C13 120.6(2) . . ? C13 C12 H12 119.7 . . ? C12 C13 H13 120.2 . . ? C14 C13 C12 119.6(2) . . ? C14 C13 H13 120.2 . . ? N1 C14 H14 119.1 . . ? C13 C14 N1 121.82(19) . . ? C13 C14 H14 119.1 . . ? O1 C15 N2 118.54(18) . . ? O1 C15 C16 124.40(18) . . ? N2 C15 C16 116.94(18) . . ? C15 C16 H16A 109.0 . . ? C15 C16 H16B 109.0 . . ? H16A C16 H16B 107.8 . . ? C17 C16 C15 113.0(2) . . ? C17 C16 H16A 109.0 . . ? C17 C16 H16B 109.0 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17B 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 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 C9 1.345(3) . ? F2 C9 1.347(2) . ? O1 C15 1.221(3) . ? N1 N2 1.425(2) . ? N1 C10 1.483(2) . ? N1 C14 1.405(3) . ? N2 C8 1.443(2) . ? N2 C15 1.367(2) . ? C1 C2 1.382(3) . ? C1 C6 1.386(3) . ? C1 C7 1.496(2) . ? C2 H2 0.9300 . ? C2 C3 1.391(3) . ? C3 H3 0.9300 . ? C3 C4 1.380(4) . ? C4 H4 0.9300 . ? C4 C5 1.367(4) . ? C5 H5 0.9300 . ? C5 C6 1.392(3) . ? C6 H6 0.9300 . ? C7 C8 1.534(3) . ? C7 C9 1.481(3) . ? C7 C10 1.573(3) . ? C8 H8 0.9800 . ? C8 C9 1.470(3) . ? C10 H10 0.9800 . ? C10 C11 1.496(3) . ? C11 H11 0.9300 . ? C11 C12 1.318(4) . ? C12 H12 0.9300 . ? C12 C13 1.444(3) . ? C13 H13 0.9300 . ? C13 C14 1.333(3) . ? C14 H14 0.9300 . ? C15 C16 1.501(3) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C16 C17 1.494(4) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 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 O1 C15 C16 C17 12.5(4) . . . . ? N1 N2 C8 C7 18.3(2) . . . . ? N1 N2 C8 C9 81.3(2) . . . . ? N1 N2 C15 O1 -165.07(18) . . . . ? N1 N2 C15 C16 18.9(3) . . . . ? N1 C10 C11 C12 -18.3(3) . . . . ? N2 N1 C10 C7 31.94(18) . . . . ? N2 N1 C10 C11 156.34(15) . . . . ? N2 N1 C14 C13 -147.5(2) . . . . ? N2 C8 C9 F1 155.96(17) . . . . ? N2 C8 C9 F2 18.7(3) . . . . ? N2 C8 C9 C7 -93.35(17) . . . . ? N2 C15 C16 C17 -171.6(3) . . . . ? C1 C2 C3 C4 -0.1(4) . . . . ? C1 C7 C8 N2 -137.43(18) . . . . ? C1 C7 C8 C9 110.5(2) . . . . ? C1 C7 C9 F1 -1.6(3) . . . . ? C1 C7 C9 F2 138.44(19) . . . . ? C1 C7 C9 C8 -110.69(19) . . . . ? C1 C7 C10 N1 119.87(18) . . . . ? C1 C7 C10 C11 -3.2(3) . . . . ? C2 C1 C6 C5 0.5(3) . . . . ? C2 C1 C7 C8 -127.1(2) . . . . ? C2 C1 C7 C9 -56.8(3) . . . . ? C2 C1 C7 C10 99.7(2) . . . . ? C2 C3 C4 C5 0.0(4) . . . . ? C3 C4 C5 C6 0.4(4) . . . . ? C4 C5 C6 C1 -0.6(4) . . . . ? C6 C1 C2 C3 -0.1(3) . . . . ? C6 C1 C7 C8 55.2(3) . . . . ? C6 C1 C7 C9 125.6(2) . . . . ? C6 C1 C7 C10 -78.0(2) . . . . ? C7 C1 C2 C3 -177.8(2) . . . . ? C7 C1 C6 C5 178.2(2) . . . . ? C7 C8 C9 F1 -110.7(2) . . . . ? C7 C8 C9 F2 112.0(2) . . . . ? C7 C10 C11 C12 100.6(2) . . . . ? C8 N2 C15 O1 -8.6(3) . . . . ? C8 N2 C15 C16 175.35(19) . . . . ? C8 C7 C9 F1 109.0(2) . . . . ? C8 C7 C9 F2 -110.9(2) . . . . ? C8 C7 C10 N1 -20.85(19) . . . . ? C8 C7 C10 C11 -143.94(18) . . . . ? C9 C7 C8 N2 112.09(18) . . . . ? C9 C7 C10 N1 -81.8(2) . . . . ? C9 C7 C10 C11 155.13(19) . . . . ? C10 N1 N2 C8 -32.3(2) . . . . ? C10 N1 N2 C15 126.5(2) . . . . ? C10 N1 C14 C13 -25.7(3) . . . . ? C10 C7 C8 N2 2.4(2) . . . . ? C10 C7 C8 C9 -109.72(17) . . . . ? C10 C7 C9 F1 -159.58(19) . . . . ? C10 C7 C9 F2 -19.5(3) . . . . ? C10 C7 C9 C8 91.37(17) . . . . ? C10 C11 C12 C13 0.2(4) . . . . ? C11 C12 C13 C14 7.1(4) . . . . ? C12 C13 C14 N1 6.3(4) . . . . ? C14 N1 N2 C8 96.31(19) . . . . ? C14 N1 N2 C15 -104.9(2) . . . . ? C14 N1 C10 C7 -94.25(19) . . . . ? C14 N1 C10 C11 30.1(2) . . . . ? C15 N2 C8 C7 -140.86(18) . . . . ? C15 N2 C8 C9 -77.9(2) . . . . ?