#------------------------------------------------------------------------------ #$Date: 2020-02-04 22:06:36 +0200 (Tue, 04 Feb 2020) $ #$Revision: 247601 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/57/7125704.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_7125704 loop_ _publ_author_name 'Fu, Wei' 'Wang, Lianhui' 'Yang, Zi' 'Shen, Jiang-Shan' 'Tang, Fei' 'Zhang, Jiayi' 'Cui, Xiuling' _publ_section_title ; Facile access to versatile aza-macrolides through iridium-catalysed cascade allyl-amination/macrolactonization. ; _journal_issue 6 _journal_name_full 'Chemical communications (Cambridge, England)' _journal_page_first 960 _journal_page_last 963 _journal_paper_doi 10.1039/c9cc07372h _journal_volume 56 _journal_year 2020 _chemical_formula_moiety 'C24 H20 F6 N2 O4' _chemical_formula_sum 'C24 H20 F6 N2 O4' _chemical_formula_weight 514.42 _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 mixed _audit_creation_date 2019-11-04 _audit_creation_method ; Olex2 1.2 (compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337) ; _audit_update_record ; 2019-11-04 deposited with the CCDC. 2019-12-06 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 91.940(3) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 10.1630(3) _cell_length_b 10.7505(3) _cell_length_c 10.3964(3) _cell_measurement_reflns_used 1608 _cell_measurement_temperature 293.1(2) _cell_measurement_theta_max 70.7180 _cell_measurement_theta_min 4.3360 _cell_volume 1135.23(6) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _diffrn_ambient_temperature 293.1(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 16.2312 _diffrn_detector_type Eos _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -108.00 -38.00 0.5000 0.5000 omega____ theta____ kappa____ phi______ frames - -33.5000 178.0000 -30.0000 140 #__ type_ start__ end____ width___ exp.time_ 2 omega -48.00 29.00 0.5000 0.5000 omega____ theta____ kappa____ phi______ frames - -33.5000 77.0000 150.0000 154 #__ type_ start__ end____ width___ exp.time_ 3 omega 66.00 106.00 0.5000 0.5000 omega____ theta____ kappa____ phi______ frames - 36.4734 178.0000 -30.0000 80 #__ type_ start__ end____ width___ exp.time_ 4 omega 58.00 95.00 0.5000 0.5000 omega____ theta____ kappa____ phi______ frames - 36.4734 178.0000 150.0000 74 #__ type_ start__ end____ width___ exp.time_ 5 omega 44.00 75.00 0.5000 0.5000 omega____ theta____ kappa____ phi______ frames - 36.4734 -99.0000 120.0000 62 #__ type_ start__ end____ width___ exp.time_ 6 omega -32.00 31.00 0.5000 0.5000 omega____ theta____ kappa____ phi______ frames - 36.4734 -37.0000 -30.0000 126 #__ type_ start__ end____ width___ exp.time_ 7 omega 35.00 96.00 0.5000 0.5000 omega____ theta____ kappa____ phi______ frames - 36.4734 57.0000 -60.0000 122 #__ type_ start__ end____ width___ exp.time_ 8 omega 38.00 72.00 0.5000 9.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -45.0000 -150.0000 68 #__ type_ start__ end____ width___ exp.time_ 9 omega 65.00 91.00 0.5000 9.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -30.0000 -30.0000 52 #__ type_ start__ end____ width___ exp.time_ 10 omega 38.00 63.00 0.5000 9.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -30.0000 150.0000 50 #__ type_ start__ end____ width___ exp.time_ 11 omega 102.00 161.00 0.5000 9.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 111.0000 0.0000 118 #__ type_ start__ end____ width___ exp.time_ 12 omega 91.00 160.00 0.5000 9.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 45.0000 -30.0000 138 #__ type_ start__ end____ width___ exp.time_ 13 omega 70.00 107.00 0.5000 9.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -94.0000 90.0000 74 #__ type_ start__ end____ width___ exp.time_ 14 omega 56.00 126.00 0.5000 9.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -61.0000 -150.0000 140 #__ type_ start__ end____ width___ exp.time_ 15 omega 99.00 173.00 0.5000 9.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 61.0000 -180.0000 148 #__ type_ start__ end____ width___ exp.time_ 16 omega 39.00 101.00 0.5000 9.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -94.0000 30.0000 124 #__ type_ start__ end____ width___ exp.time_ 17 omega 38.00 85.00 0.5000 9.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -30.0000 30.0000 94 #__ type_ start__ end____ width___ exp.time_ 18 omega 39.00 80.00 0.5000 9.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -30.0000 -150.0000 82 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.1420934000 _diffrn_orient_matrix_UB_12 -0.0030533000 _diffrn_orient_matrix_UB_13 0.0566327000 _diffrn_orient_matrix_UB_21 -0.0352486000 _diffrn_orient_matrix_UB_22 -0.1128473000 _diffrn_orient_matrix_UB_23 0.0833889000 _diffrn_orient_matrix_UB_31 0.0399403000 _diffrn_orient_matrix_UB_32 -0.0882739000 _diffrn_orient_matrix_UB_33 -0.1086255000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0275 _diffrn_reflns_av_unetI/netI 0.0345 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 4348 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 67.068 _diffrn_reflns_theta_max 67.068 _diffrn_reflns_theta_min 4.353 _diffrn_source 'Enhance (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 1.184 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.77022 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.505 _exptl_crystal_description prism _exptl_crystal_F_000 528 _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.221 _refine_diff_density_min -0.171 _refine_diff_density_rms 0.048 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 195 _refine_ls_number_reflns 2029 _refine_ls_number_restraints 38 _refine_ls_restrained_S_all 1.088 _refine_ls_R_factor_all 0.0596 _refine_ls_R_factor_gt 0.0481 _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^)+(0.0792P)^2^+0.2074P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1290 _refine_ls_wR_factor_ref 0.1455 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1663 _reflns_number_total 2029 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9cc07372h2.cif _cod_data_source_block anti-3m _cod_depositor_comments 'Adding full bibliography for 7125703--7125707.cif.' _cod_original_cell_volume 1135.22(6) _cod_database_code 7125704 _shelx_shelxl_version_number 2018/1 _chemical_oxdiff_formula C21H22N3O3 _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 0.891 _shelx_estimated_absorpt_t_min 0.833 _reflns_odcompleteness_completeness 99.95 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups 2. Restrained distances F3A-C11 1.37 with sigma of 0.02 C11-F2A 1.37 with sigma of 0.02 3. Uiso/Uaniso restraints and constraints Uanis(F1) \\sim Ueq, Uanis(F1A) \\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(F2A) \\sim Ueq, Uanis(F3) \\sim Ueq, Uanis(F3A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02 4. Others Sof(F1A)=Sof(F2A)=Sof(F3A)=1-FVAR(1) Sof(F1)=Sof(F2)=Sof(F3)=FVAR(1) 5.a Ternary CH refined with riding coordinates: C8(H8) 5.b Secondary CH2 refined with riding coordinates: C0AA(H0AA,H0AB) 5.c Aromatic/amide H refined with riding coordinates: C6(H6), C4(H4), C3(H3), C9(H9) 5.d X=CH2 refined with riding coordinates: C10(H10A,H10B) ; _shelx_res_file ; TITL 201907181 in P21/c #14 anti-3m.res created by SHELXL-2018/1 at 09:39:00 on 04-Nov-2019 REM reset to P21/c #14 CELL 1.54184 10.162977 10.7505 10.396352 90 91.9398 90 ZERR 2 0.000319 0.000329 0.000292 0 0.0026 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H F N O UNIT 48 40 12 4 8 DFIX 1.37 F3A C11 DFIX 1.37 C11 F2A ISOR 0.01 0.02 F1 F1A F2 F2A F3 F3A L.S. 8 0 0 PLAN 4 SIZE 0.1 0.13 0.16 TEMP 20.0(2) bond $h conf fmap 2 acta REM REM REM WGHT 0.079200 0.207400 FVAR 7.71023 0.61029 C1 1 0.750847 0.445774 -0.042712 11.00000 0.04467 0.04163 = 0.04132 0.00298 0.00854 0.00440 C6 1 0.650785 0.355823 -0.037673 11.00000 0.04839 0.05037 = 0.04529 -0.00048 0.00613 -0.00261 AFIX 43 H6 2 0.632116 0.306166 -0.109233 11.00000 -1.20000 AFIX 0 C5 1 0.580100 0.340264 0.071707 11.00000 0.04435 0.04923 = 0.05523 0.00936 0.00801 0.00434 C4 1 0.605672 0.410813 0.181412 11.00000 0.05495 0.05737 = 0.04908 0.00514 0.01943 0.00370 AFIX 43 H4 2 0.555766 0.400846 0.254048 11.00000 -1.20000 AFIX 0 C3 1 0.706594 0.495802 0.180085 11.00000 0.05727 0.05097 = 0.04302 -0.00221 0.01312 0.00541 AFIX 43 H3 2 0.726108 0.542226 0.253766 11.00000 -1.20000 AFIX 0 C2 1 0.780702 0.514299 0.070855 11.00000 0.04639 0.03957 = 0.04311 0.00075 0.00832 0.00609 C7 1 0.891101 0.604137 0.075638 11.00000 0.05161 0.04005 = 0.04229 -0.00431 0.00932 0.00560 C0AA 1 1.046902 0.708251 0.214521 11.00000 0.06900 0.04648 = 0.04861 -0.01315 0.00836 -0.00780 AFIX 23 H0AA 2 1.033942 0.769888 0.281044 11.00000 -1.20000 H0AB 2 1.065394 0.751520 0.135277 11.00000 -1.20000 AFIX 0 C8 1 0.837962 0.375375 -0.253067 11.00000 0.05372 0.05580 = 0.04205 -0.01095 0.00935 -0.01265 AFIX 13 H8 2 0.759244 0.323023 -0.262029 11.00000 -1.20000 AFIX 0 C9 1 0.858620 0.436452 -0.381082 11.00000 0.06649 0.08060 = 0.04110 -0.00774 0.00743 -0.00577 AFIX 43 H9 2 0.896203 0.387565 -0.443857 11.00000 -1.20000 AFIX 0 C10 1 0.829600 0.549926 -0.413123 11.00000 0.07820 0.09397 = 0.05735 0.01503 0.00552 0.00354 AFIX 93 H10A 2 0.791814 0.602739 -0.353902 11.00000 -1.20000 H10B 2 0.846561 0.578545 -0.495337 11.00000 -1.20000 AFIX 0 C11 1 0.475173 0.242532 0.072158 11.00000 0.05491 0.06599 = 0.06274 0.00892 0.01191 -0.00538 PART 1 F1 3 0.437879 0.201860 -0.042849 21.00000 0.14106 0.18545 = 0.07295 -0.03901 0.04152 -0.11042 PART 0 PART 2 F1A 3 0.514439 0.133346 0.083297 -21.00000 0.09493 0.04489 = 0.22787 0.01701 -0.02611 0.00333 PART 0 PART 1 F2 3 0.515652 0.144070 0.141129 21.00000 0.07249 0.07006 = 0.15281 0.04882 -0.01208 -0.02085 PART 0 PART 2 F2A 3 0.389284 0.259147 0.160101 -21.00000 0.15463 0.16694 = 0.13214 -0.02408 0.09305 -0.08437 PART 0 PART 1 F3 3 0.367458 0.278441 0.128439 21.00000 0.04096 0.08126 = 0.14142 0.01161 0.02783 0.00324 PART 0 PART 2 F3A 3 0.406568 0.240654 -0.033865 -21.00000 0.07526 0.10507 = 0.13705 0.04182 -0.04574 -0.03976 PART 0 N1 4 0.813688 0.468456 -0.155085 11.00000 0.05477 0.04901 = 0.04123 -0.00496 0.01205 -0.00883 O2 5 0.944140 0.645665 -0.018204 11.00000 0.06877 0.05031 = 0.04290 -0.00117 0.01117 -0.01196 O1 5 0.929280 0.633981 0.196512 11.00000 0.05537 0.05908 = 0.04296 -0.00993 0.00990 -0.00360 H1 2 0.877126 0.529297 -0.148361 11.00000 0.05773 HKLF 4 REM 201907181 in P21/c #14 REM R1 = 0.0481 for 1663 Fo > 4sig(Fo) and 0.0596 for all 2029 data REM 195 parameters refined using 38 restraints END WGHT 0.0792 0.2074 REM Highest difference peak 0.221, deepest hole -0.171, 1-sigma level 0.048 Q1 1 0.5281 0.1488 -0.0158 11.00000 0.05 0.22 Q2 1 0.4751 0.1949 0.2046 11.00000 0.05 0.22 Q3 1 0.6384 0.3246 0.0386 11.00000 0.05 0.21 Q4 1 0.8181 0.4530 -0.4748 11.00000 0.05 0.20 ; _shelx_res_checksum 43900 _olex2_submission_special_instructions 'No special instructions were received' 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 C1 C 0.75085(18) 0.44577(17) -0.04271(17) 0.0424(4) Uani 1 1 d . . . . . C6 C 0.65078(19) 0.35582(19) -0.03767(19) 0.0479(4) Uani 1 1 d . . . . . H6 H 0.632116 0.306166 -0.109233 0.057 Uiso 1 1 calc R . . . . C5 C 0.58010(19) 0.34026(19) 0.0717(2) 0.0495(5) Uani 1 1 d . . . . . C4 C 0.6057(2) 0.4108(2) 0.18141(19) 0.0534(5) Uani 1 1 d . . . . . H4 H 0.555766 0.400846 0.254048 0.064 Uiso 1 1 calc R . . . . C3 C 0.7066(2) 0.49580(19) 0.18008(19) 0.0502(5) Uani 1 1 d . . . . . H3 H 0.726108 0.542226 0.253766 0.060 Uiso 1 1 calc R . . . . C2 C 0.78070(18) 0.51430(16) 0.07085(17) 0.0429(4) Uani 1 1 d . . . . . C7 C 0.89110(19) 0.60414(17) 0.07564(17) 0.0445(4) Uani 1 1 d . . . . . C0AA C 1.0469(2) 0.70825(19) 0.2145(2) 0.0546(5) Uani 1 1 d . . . . . H0AA H 1.033942 0.769888 0.281044 0.065 Uiso 1 1 calc R . . . . H0AB H 1.065394 0.751520 0.135277 0.065 Uiso 1 1 calc R . . . . C8 C 0.8380(2) 0.37537(19) -0.25307(18) 0.0503(5) Uani 1 1 d . . . . . H8 H 0.759244 0.323023 -0.262029 0.060 Uiso 1 1 calc R . . . . C9 C 0.8586(2) 0.4365(2) -0.3811(2) 0.0626(6) Uani 1 1 d . . . . . H9 H 0.896203 0.387565 -0.443857 0.075 Uiso 1 1 calc R . . . . C10 C 0.8296(3) 0.5499(3) -0.4131(3) 0.0764(7) Uani 1 1 d . . . . . H10A H 0.791814 0.602739 -0.353902 0.092 Uiso 1 1 calc R . . . . H10B H 0.846561 0.578545 -0.495337 0.092 Uiso 1 1 calc R . . . . C11 C 0.4752(2) 0.2425(2) 0.0722(2) 0.0610(6) Uani 1 1 d D . . . . F1 F 0.4379(10) 0.2019(12) -0.0428(5) 0.132(3) Uani 0.610(19) 1 d . U P A 1 F1A F 0.5144(14) 0.1333(11) 0.083(2) 0.123(5) Uani 0.390(19) 1 d . U P A 2 F2 F 0.5157(8) 0.1441(8) 0.1411(10) 0.099(2) Uani 0.610(19) 1 d . U P A 1 F2A F 0.3893(17) 0.2591(17) 0.1601(19) 0.149(5) Uani 0.390(19) 1 d D U P A 2 F3 F 0.3675(4) 0.2784(6) 0.1284(7) 0.0873(17) Uani 0.610(19) 1 d . U P A 1 F3A F 0.4066(10) 0.2407(11) -0.0339(11) 0.107(4) Uani 0.390(19) 1 d D U P A 2 N1 N 0.81369(17) 0.46846(16) -0.15508(15) 0.0481(4) Uani 1 1 d . . . . . O2 O 0.94414(15) 0.64567(13) -0.01820(13) 0.0538(4) Uani 1 1 d . . . . . O1 O 0.92928(14) 0.63398(14) 0.19651(13) 0.0523(4) Uani 1 1 d . . . . . H1 H 0.877(3) 0.529(3) -0.148(2) 0.058(6) 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 C1 0.0447(9) 0.0416(9) 0.0413(9) 0.0030(7) 0.0085(7) 0.0044(7) C6 0.0484(10) 0.0504(10) 0.0453(9) -0.0005(7) 0.0061(7) -0.0026(8) C5 0.0443(9) 0.0492(10) 0.0552(11) 0.0094(8) 0.0080(8) 0.0043(8) C4 0.0549(11) 0.0574(11) 0.0491(10) 0.0051(9) 0.0194(8) 0.0037(9) C3 0.0573(11) 0.0510(10) 0.0430(9) -0.0022(8) 0.0131(8) 0.0054(9) C2 0.0464(9) 0.0396(8) 0.0431(9) 0.0007(7) 0.0083(7) 0.0061(7) C7 0.0516(10) 0.0401(9) 0.0423(9) -0.0043(7) 0.0093(7) 0.0056(7) C0AA 0.0690(13) 0.0465(10) 0.0486(10) -0.0132(8) 0.0084(9) -0.0078(9) C8 0.0537(10) 0.0558(11) 0.0421(9) -0.0109(8) 0.0094(8) -0.0126(9) C9 0.0665(13) 0.0806(15) 0.0411(10) -0.0077(10) 0.0074(9) -0.0058(11) C10 0.0782(16) 0.0940(19) 0.0573(13) 0.0150(13) 0.0055(11) 0.0035(14) C11 0.0549(12) 0.0660(14) 0.0627(13) 0.0089(10) 0.0119(10) -0.0054(10) F1 0.141(5) 0.185(7) 0.073(3) -0.039(3) 0.042(3) -0.110(5) F1A 0.095(5) 0.045(3) 0.228(14) 0.017(6) -0.026(7) 0.003(3) F2 0.072(2) 0.070(3) 0.153(5) 0.049(3) -0.012(3) -0.021(2) F2A 0.155(10) 0.167(10) 0.132(7) -0.024(6) 0.093(7) -0.084(7) F3 0.0410(18) 0.081(2) 0.141(5) 0.012(2) 0.028(2) 0.0032(16) F3A 0.075(4) 0.105(5) 0.137(8) 0.042(5) -0.046(5) -0.040(3) N1 0.0548(9) 0.0490(9) 0.0412(8) -0.0050(7) 0.0120(6) -0.0088(7) O2 0.0688(9) 0.0503(8) 0.0429(7) -0.0012(6) 0.0112(6) -0.0120(6) O1 0.0554(8) 0.0591(8) 0.0430(7) -0.0099(6) 0.0099(6) -0.0036(6) 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 C6 C1 C2 117.50(16) . . N1 C1 C6 120.81(17) . . N1 C1 C2 121.65(17) . . C1 C6 H6 119.6 . . C5 C6 C1 120.88(19) . . C5 C6 H6 119.6 . . C6 C5 C4 121.65(19) . . C6 C5 C11 118.7(2) . . C4 C5 C11 119.66(19) . . C5 C4 H4 120.8 . . C3 C4 C5 118.33(17) . . C3 C4 H4 120.8 . . C4 C3 H3 119.1 . . C4 C3 C2 121.71(19) . . C2 C3 H3 119.1 . . C1 C2 C7 120.56(16) . . C3 C2 C1 119.82(18) . . C3 C2 C7 119.62(17) . . O2 C7 C2 124.68(17) . . O2 C7 O1 122.82(18) . . O1 C7 C2 112.49(16) . . H0AA C0AA H0AB 108.2 . . C8 C0AA H0AA 109.8 3_765 . C8 C0AA H0AB 109.8 3_765 . O1 C0AA H0AA 109.8 . . O1 C0AA H0AB 109.8 . . O1 C0AA C8 109.50(16) . 3_765 C0AA C8 H8 107.7 3_765 . C9 C8 C0AA 111.24(18) . 3_765 C9 C8 H8 107.7 . . N1 C8 C0AA 111.70(16) . 3_765 N1 C8 H8 107.7 . . N1 C8 C9 110.55(18) . . C8 C9 H9 116.5 . . C10 C9 C8 126.9(2) . . C10 C9 H9 116.5 . . C9 C10 H10A 120.0 . . C9 C10 H10B 120.0 . . H10A C10 H10B 120.0 . . F1 C11 C5 114.4(3) . . F1 C11 F2 107.4(5) . . F1A C11 C5 115.9(7) . . F1A C11 F2A 106.6(9) . . F1A C11 F3A 103.2(9) . . F2 C11 C5 110.6(4) . . F2A C11 C5 113.7(7) . . F3 C11 C5 113.5(4) . . F3 C11 F1 106.4(5) . . F3 C11 F2 103.9(5) . . F3A C11 C5 112.0(5) . . F3A C11 F2A 104.4(9) . . C1 N1 C8 124.66(16) . . C1 N1 H1 114.0(16) . . C8 N1 H1 114.0(16) . . C7 O1 C0AA 117.74(15) . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 C1 C6 1.406(3) . C1 C2 1.416(3) . C1 N1 1.372(2) . C6 H6 0.9300 . C6 C5 1.376(3) . C5 C4 1.387(3) . C5 C11 1.497(3) . C4 H4 0.9300 . C4 C3 1.374(3) . C3 H3 0.9300 . C3 C2 1.398(3) . C2 C7 1.480(3) . C7 O2 1.215(2) . C7 O1 1.342(2) . C0AA H0AA 0.9700 . C0AA H0AB 0.9700 . C0AA C8 1.519(3) 3_765 C0AA O1 1.444(3) . C8 H8 0.9800 . C8 C9 1.505(3) . C8 N1 1.455(2) . C9 H9 0.9300 . C9 C10 1.296(4) . C10 H10A 0.9300 . C10 H10B 0.9300 . C11 F1 1.317(6) . C11 F1A 1.244(12) . C11 F2 1.336(8) . C11 F2A 1.298(11) . C11 F3 1.316(5) . C11 F3A 1.284(9) . N1 H1 0.92(3) . 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 C1 C6 C5 C4 -1.0(3) . C1 C6 C5 C11 -179.62(18) . C1 C2 C7 O2 16.4(3) . C1 C2 C7 O1 -162.35(16) . C6 C1 C2 C3 -3.5(3) . C6 C1 C2 C7 175.62(16) . C6 C1 N1 C8 -32.1(3) . C6 C5 C4 C3 -1.6(3) . C6 C5 C11 F1 -16.4(8) . C6 C5 C11 F1A 75.9(13) . C6 C5 C11 F2 104.9(5) . C6 C5 C11 F2A -160.1(13) . C6 C5 C11 F3 -138.8(4) . C6 C5 C11 F3A -42.1(7) . C5 C4 C3 C2 1.6(3) . C4 C5 C11 F1 164.9(7) . C4 C5 C11 F1A -102.8(13) . C4 C5 C11 F2 -73.7(6) . C4 C5 C11 F2A 21.2(13) . C4 C5 C11 F3 42.5(4) . C4 C5 C11 F3A 139.2(7) . C4 C3 C2 C1 1.0(3) . C4 C3 C2 C7 -178.09(18) . C3 C2 C7 O2 -164.49(19) . C3 C2 C7 O1 16.7(2) . C2 C1 C6 C5 3.5(3) . C2 C1 N1 C8 150.04(19) . C2 C7 O1 C0AA 172.20(16) . C0AA C8 C9 C10 -140.4(3) 3_765 C0AA C8 N1 C1 -77.6(2) 3_765 C8 C0AA O1 C7 -100.08(19) 3_765 C9 C8 N1 C1 157.91(18) . C11 C5 C4 C3 177.03(19) . N1 C1 C6 C5 -174.46(18) . N1 C1 C2 C3 174.44(18) . N1 C1 C2 C7 -6.5(3) . N1 C8 C9 C10 -15.7(3) . O2 C7 O1 C0AA -6.6(3) .