#------------------------------------------------------------------------------ #$Date: 2019-11-13 06:22:57 +0200 (Wed, 13 Nov 2019) $ #$Revision: 227690 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/72/7157202.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_7157202 loop_ _publ_author_name 'Galeev, Andrew R.' 'Mokrushin, Ivan G.' 'Dmitriev, Maksim V.' 'Mashevskaya, Irina V.' 'Maslivets, Andrey N.' 'Rubin, Michael' _publ_section_title ; Synthesis of meta-Substituted Anilines via Three-Component Reaction of Acetone, Amines, and 1,3-Diketones ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/C9OB02120E _journal_year 2019 _chemical_formula_moiety 'C16 H16 F3 N O S' _chemical_formula_sum 'C16 H16 F3 N O S' _chemical_formula_weight 327.36 _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 geom _atom_sites_solution_primary iterative _audit_creation_date 2019-10-23 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2019-10-23 deposited with the CCDC. 2019-11-12 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 106.57(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 13.153(4) _cell_length_b 15.177(5) _cell_length_c 7.937(2) _cell_measurement_reflns_used 2321 _cell_measurement_temperature 295(2) _cell_measurement_theta_max 26.7880 _cell_measurement_theta_min 3.6700 _cell_volume 1518.6(8) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET) (compiled Mar 27 2014,17:12:48) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET) (compiled Mar 27 2014,17:12:48) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET) (compiled Mar 27 2014,17:12:48) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution ; Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008; Palatinus et al., 2012) ; _diffrn_ambient_temperature 295.15 _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 10.4752 _diffrn_detector_type Ruby _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.841 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -27.00 38.00 1.0000 7.0000 omega____ theta____ kappa____ phi______ frames - 14.1634 -38.0000 -120.0000 65 #__ type_ start__ end____ width___ exp.time_ 2 omega -22.00 3.00 1.0000 7.0000 omega____ theta____ kappa____ phi______ frames - 14.1634 77.0000 -180.0000 25 #__ type_ start__ end____ width___ exp.time_ 3 omega 22.00 97.00 1.0000 7.0000 omega____ theta____ kappa____ phi______ frames - 14.1634 77.0000 -180.0000 75 #__ type_ start__ end____ width___ exp.time_ 4 omega -10.00 26.00 1.0000 7.0000 omega____ theta____ kappa____ phi______ frames - -14.7103 -99.0000 60.0000 36 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'New Xcalibur, Ruby' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0070603000 _diffrn_orient_matrix_UB_12 -0.0389217000 _diffrn_orient_matrix_UB_13 0.0518727000 _diffrn_orient_matrix_UB_21 -0.0076974000 _diffrn_orient_matrix_UB_22 -0.0258331000 _diffrn_orient_matrix_UB_23 -0.0767036000 _diffrn_orient_matrix_UB_31 0.0553520000 _diffrn_orient_matrix_UB_32 0.0012360000 _diffrn_orient_matrix_UB_33 0.0096203000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0335 _diffrn_reflns_av_unetI/netI 0.0498 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.841 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_number 7255 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.841 _diffrn_reflns_theta_full 26.000 _diffrn_reflns_theta_max 29.423 _diffrn_reflns_theta_min 3.232 _diffrn_source 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.246 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.67108 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET) (compiled Mar 27 2014,17:12:48) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.432 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 680 _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.26 _refine_diff_density_max 0.191 _refine_diff_density_min -0.247 _refine_diff_density_rms 0.056 _refine_ls_extinction_coef 0.135(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2018/1 (Sheldrick 2018)' _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 266 _refine_ls_number_reflns 3526 _refine_ls_number_restraints 42 _refine_ls_restrained_S_all 1.033 _refine_ls_R_factor_all 0.0756 _refine_ls_R_factor_gt 0.0479 _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^)+(0.0543P)^2^+0.1001P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1065 _refine_ls_wR_factor_ref 0.1271 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2418 _reflns_number_total 3526 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9ob02120e2.cif _cod_data_source_block psu-1012(b-344) _cod_database_code 7157202 _shelx_shelxl_version_number 2018/1 _chemical_oxdiff_formula 'C H N O S F' _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 0.939 _shelx_estimated_absorpt_t_min 0.877 _reflns_odcompleteness_completeness 99.66 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _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. Restrained distances S1-C8 \\sim S1A-C8 with sigma of 0.02 S1-C11 \\sim S1A-C11A with sigma of 0.02 C8-C9 \\sim C8-C9A with sigma of 0.02 C9-C10 \\sim C9A-C10A with sigma of 0.02 C10-C11 \\sim C10A-C11A with sigma of 0.02 S1-C10 \\sim S1A-C10A with sigma of 0.04 C8-C10 \\sim C8-C10A with sigma of 0.04 C8-C11 \\sim C8-C11A with sigma of 0.04 C9-C11 \\sim C9A-C11A with sigma of 0.04 F1-C12 \\sim F1A-C12 with sigma of 0.02 F2-C12 \\sim F2A-C12 with sigma of 0.02 F3-C12 \\sim F3A-C12 with sigma of 0.02 3. Rigid bond restraints F1, F1A, F2, F2A, F3, F3A with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01 4. Uiso/Uaniso restraints and constraints F1 \\sim F1A \\sim F2 \\sim F2A \\sim F3 \\sim F3A: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08 5. Others Sof(S1A)=Sof(C9A)=Sof(H9A)=Sof(C10A)=Sof(H10A)=Sof(C11A)=Sof(H11A)=1-FVAR(1) Sof(S1)=Sof(C9)=Sof(H9)=Sof(C10)=Sof(H10)=Sof(C11)=Sof(H11)=FVAR(1) Sof(F1A)=Sof(F2A)=Sof(F3A)=1-FVAR(2) Sof(F1)=Sof(F2)=Sof(F3)=FVAR(2) 6.a Secondary CH2 refined with riding coordinates: C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B) 6.b Aromatic/amide H refined with riding coordinates: C2(H2), C4(H4), C9(H9), C9A(H9A), C10(H10), C10A(H10A), C11(H11), C11A(H11A) 6.c Idealised Me refined as rotating group: C7(H7A,H7B,H7C) ; _shelx_res_file ; TITL CF solution in P21/c psu-1012(b-344).res created by SHELXL-2018/1 at 01:39:22 on 23-Oct-2019 CELL 0.71073 13.15283 15.17679 7.93725 90 106.5662 90 ZERR 4 0.00361 0.00477 0.00206 0 0.0289 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H F N O S UNIT 64 64 12 4 4 4 SADI S1 C8 S1A C8 SADI S1 C11 S1A C11A SADI C8 C9 C8 C9A SADI C9 C10 C9A C10A SADI C10 C11 C10A C11A SADI 0.04 S1 C10 S1A C10A SADI 0.04 C8 C10 C8 C10A SADI 0.04 C8 C11 C8 C11A SADI 0.04 C9 C11 C9A C11A SADI F1 C12 F1A C12 SADI F2 C12 F2A C12 SADI F3 C12 F3A C12 DELU F1 F1A F2 F2A F3 F3A SIMU 0.04 0.08 1.7 F1 F1A F2 F2A F3 F3A L.S. 10 PLAN 25 SIZE 0.26 0.35 0.55 TEMP 22 BOND fmap 2 acta 52 REM REM REM WGHT 0.054300 0.100100 EXTI 0.135123 FVAR 10.01249 0.74145 0.59282 C1 1 0.271158 0.521669 0.233550 11.00000 0.04074 0.02865 = 0.03840 -0.00246 0.01040 -0.00348 N1 4 0.221447 0.591391 0.120432 11.00000 0.04155 0.03434 = 0.04040 0.00403 0.01144 -0.00270 O1 5 0.123088 0.693756 -0.180880 11.00000 0.07093 0.06574 = 0.04560 0.01672 0.01140 -0.00054 PART 1 F1 3 0.578454 0.428769 0.281781 31.00000 0.05176 0.07235 = 0.16763 -0.03268 0.05613 -0.01676 S1 6 0.311768 0.367609 0.813999 21.00000 0.07178 0.06344 = 0.04762 0.01575 0.01194 -0.00443 PART 0 PART 2 F1A 3 0.580698 0.361037 0.450378 -31.00000 0.04235 0.16323 = 0.09728 -0.06489 -0.01819 0.03012 S1A 6 0.104936 0.362655 0.584167 -21.00000 0.04319 0.04892 = 0.05454 0.00383 0.02433 -0.00278 PART 0 C2 1 0.364396 0.483418 0.218728 11.00000 0.04211 0.04227 = 0.04326 -0.00121 0.01642 -0.00294 AFIX 43 H2 2 0.395177 0.503537 0.133981 11.00000 -1.20000 AFIX 0 PART 1 F2 3 0.560809 0.327716 0.448141 31.00000 0.09977 0.19017 = 0.12359 0.08652 0.06048 0.09702 PART 0 PART 2 F2A 3 0.497497 0.296282 0.239243 -31.00000 0.06724 0.07940 = 0.22895 -0.08684 0.02203 0.00690 PART 0 C3 1 0.411249 0.415529 0.329960 11.00000 0.03922 0.04014 = 0.04890 -0.00536 0.01261 0.00410 PART 1 F3 3 0.489178 0.318269 0.179485 31.00000 0.06401 0.11396 = 0.11162 -0.06826 0.01019 0.03034 PART 0 PART 2 F3A 3 0.550996 0.418630 0.203500 -31.00000 0.13242 0.18034 = 0.24436 0.11652 0.15021 0.08582 PART 0 C4 1 0.365659 0.384302 0.453637 11.00000 0.04567 0.03544 = 0.04935 0.00392 0.01300 0.00455 AFIX 43 H4 2 0.396295 0.337037 0.524620 11.00000 -1.20000 AFIX 0 C5 1 0.273625 0.423088 0.473403 11.00000 0.04141 0.03175 = 0.04060 -0.00122 0.01202 -0.00112 C6 1 0.226893 0.494029 0.367167 11.00000 0.03936 0.02839 = 0.04018 -0.00204 0.01242 0.00024 C7 1 0.137506 0.544996 0.404544 11.00000 0.05546 0.03729 = 0.05652 0.00595 0.02545 0.00951 AFIX 137 H7A 2 0.071572 0.515393 0.351997 11.00000 -1.50000 H7B 2 0.135020 0.603199 0.356172 11.00000 -1.50000 H7C 2 0.148937 0.548888 0.529291 11.00000 -1.50000 AFIX 0 C8 1 0.230254 0.388767 0.613070 11.00000 0.04951 0.03020 = 0.04442 0.00249 0.01544 0.00384 PART 1 C9 1 0.129629 0.363566 0.605966 21.00000 0.06609 0.05945 = 0.05333 0.00180 0.01889 0.00305 AFIX 43 H9 2 0.073307 0.367113 0.503990 21.00000 -1.20000 AFIX 0 PART 0 PART 2 C9A 1 0.286688 0.363136 0.777110 -21.00000 0.08033 0.17187 = 0.22094 -0.00123 0.00807 -0.04509 AFIX 43 H9A 2 0.358859 0.374626 0.821492 -21.00000 -1.20000 AFIX 0 PART 0 PART 1 C10 1 0.118190 0.331485 0.767353 21.00000 0.06732 0.03098 = 0.07466 0.00669 0.03840 0.00414 AFIX 43 H10 2 0.054312 0.313641 0.784824 21.00000 -1.20000 AFIX 0 PART 0 PART 2 C10A 1 0.228992 0.317721 0.876992 -21.00000 0.07053 0.04613 = 0.05553 0.02418 0.01492 0.02535 AFIX 43 H10A 2 0.256962 0.295586 0.990025 -21.00000 -1.20000 AFIX 0 PART 0 PART 1 C11 1 0.211189 0.330370 0.890350 21.00000 0.10042 0.03856 = 0.05020 0.00526 0.03719 0.00288 AFIX 43 H11 2 0.220214 0.311385 1.005092 21.00000 -1.20000 AFIX 0 PART 0 PART 2 C11A 1 0.128735 0.312359 0.781583 -21.00000 0.08117 0.01024 = 0.04348 -0.00131 0.02365 -0.00294 AFIX 43 H11A 2 0.076605 0.283796 0.819322 -21.00000 -1.20000 AFIX 0 PART 0 C12 1 0.509376 0.373470 0.309090 11.00000 0.04583 0.05522 = 0.06603 -0.00272 0.01937 0.00743 C13 1 0.117486 0.568730 0.004061 11.00000 0.04860 0.04646 = 0.04924 0.00551 0.00495 -0.00761 AFIX 23 H13A 2 0.075000 0.540867 0.070836 11.00000 -1.20000 H13B 2 0.125234 0.527554 -0.084931 11.00000 -1.20000 AFIX 0 C14 1 0.063523 0.650972 -0.081835 11.00000 0.05459 0.06057 = 0.05571 0.01462 0.01034 0.00156 AFIX 23 H14A 2 -0.006011 0.636058 -0.158557 11.00000 -1.20000 H14B 2 0.053799 0.690874 0.007781 11.00000 -1.20000 AFIX 0 C15 1 0.224632 0.715643 -0.067958 11.00000 0.07046 0.05495 = 0.05585 0.01586 0.01719 -0.00815 AFIX 23 H15A 2 0.216487 0.756327 0.021553 11.00000 -1.20000 H15B 2 0.265758 0.744868 -0.135393 11.00000 -1.20000 AFIX 0 C16 1 0.283272 0.635100 0.018914 11.00000 0.05334 0.05166 = 0.05247 0.00893 0.01916 -0.00581 AFIX 23 H16A 2 0.294394 0.595172 -0.069607 11.00000 -1.20000 H16B 2 0.352057 0.651893 0.095772 11.00000 -1.20000 AFIX 0 HKLF 4 REM CF solution in P21/c REM R1 = 0.0479 for 2418 Fo > 4sig(Fo) and 0.0756 for all 3526 data REM 266 parameters refined using 42 restraints END WGHT 0.0543 0.1001 REM Highest difference peak 0.191, deepest hole -0.247, 1-sigma level 0.056 Q1 1 0.3824 0.3855 0.8415 11.00000 0.05 0.19 Q2 1 0.0795 0.5135 0.0061 11.00000 0.05 0.19 Q3 1 0.2639 0.5209 0.3381 11.00000 0.05 0.18 Q4 1 0.4566 0.4025 0.3208 11.00000 0.05 0.17 Q5 1 0.4003 0.2332 0.2857 11.00000 0.05 0.17 Q6 1 0.2153 0.4730 -0.1147 11.00000 0.05 0.17 Q7 1 0.2189 0.6352 0.3466 11.00000 0.05 0.17 Q8 1 0.3400 0.6566 0.2623 11.00000 0.05 0.17 Q9 1 0.3450 0.6862 0.1329 11.00000 0.05 0.16 Q10 1 0.6226 0.5089 0.2327 11.00000 0.05 0.15 Q11 1 0.2967 0.5389 0.5046 11.00000 0.05 0.15 Q12 1 0.2059 0.5209 0.3914 11.00000 0.05 0.15 Q13 1 0.0800 0.6444 0.5306 11.00000 0.05 0.15 Q14 1 0.3331 0.4926 0.5862 11.00000 0.05 0.15 Q15 1 0.2812 0.4943 0.6798 11.00000 0.05 0.15 Q16 1 0.2582 0.4788 0.7274 11.00000 0.05 0.15 Q17 1 0.3149 0.5957 0.3294 11.00000 0.05 0.14 Q18 1 0.0528 0.2624 0.6801 11.00000 0.05 0.14 Q19 1 0.3953 0.6569 0.2690 11.00000 0.05 0.14 Q20 1 0.3582 0.4437 0.8856 11.00000 0.05 0.13 Q21 1 0.3092 0.8193 -0.1497 11.00000 0.05 0.13 Q22 1 0.2334 0.5033 0.3090 11.00000 0.05 0.13 Q23 1 0.2588 0.6313 0.4346 11.00000 0.05 0.13 Q24 1 0.4191 0.3181 0.8853 11.00000 0.05 0.13 Q25 1 0.0211 0.7804 -0.0945 11.00000 0.05 0.13 ; _shelx_res_checksum 4311 _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 0.27116(12) 0.52167(11) 0.23355(19) 0.0361(4) Uani 1 1 d . . . . . N1 N 0.22145(10) 0.59139(9) 0.12043(16) 0.0388(4) Uani 1 1 d . . . . . O1 O 0.12309(11) 0.69376(10) -0.18088(15) 0.0618(4) Uani 1 1 d . . . . . F1 F 0.5785(4) 0.4288(4) 0.2818(10) 0.092(2) Uani 0.593(15) 1 d D U P A 1 S1 S 0.31177(13) 0.36761(9) 0.81400(15) 0.0620(4) Uani 0.741(4) 1 d D . P B 1 F1A F 0.5807(7) 0.3610(9) 0.4504(12) 0.109(4) Uani 0.407(15) 1 d D U P A 2 S1A S 0.1049(7) 0.3627(6) 0.5842(11) 0.0467(11) Uani 0.259(4) 1 d D . P B 2 C2 C 0.36440(12) 0.48342(12) 0.2187(2) 0.0417(4) Uani 1 1 d . . . . . H2 H 0.395177 0.503537 0.133981 0.050 Uiso 1 1 calc R . . . . F2 F 0.5608(7) 0.3277(8) 0.4481(9) 0.132(3) Uani 0.593(15) 1 d D U P A 1 F2A F 0.4975(12) 0.2963(10) 0.239(3) 0.129(6) Uani 0.407(15) 1 d D U P A 2 C3 C 0.41125(12) 0.41553(12) 0.3300(2) 0.0427(4) Uani 1 1 d . . . . . F3 F 0.4892(8) 0.3183(7) 0.1795(11) 0.100(3) Uani 0.593(15) 1 d D U P A 1 F3A F 0.5510(13) 0.4186(10) 0.204(3) 0.166(5) Uani 0.407(15) 1 d D U P A 2 C4 C 0.36566(13) 0.38430(12) 0.4536(2) 0.0436(4) Uani 1 1 d . . . . . H4 H 0.396295 0.337037 0.524620 0.052 Uiso 1 1 calc R . . . . C5 C 0.27363(13) 0.42309(11) 0.47340(19) 0.0379(4) Uani 1 1 d . . . . . C6 C 0.22689(12) 0.49403(11) 0.36717(19) 0.0358(4) Uani 1 1 d . . . . . C7 C 0.13751(14) 0.54500(12) 0.4045(2) 0.0478(4) Uani 1 1 d . . . . . H7A H 0.071572 0.515393 0.351997 0.072 Uiso 1 1 calc GR . . . . H7B H 0.135020 0.603199 0.356172 0.072 Uiso 1 1 calc GR . . . . H7C H 0.148937 0.548888 0.529291 0.072 Uiso 1 1 calc GR . . . . C8 C 0.23025(15) 0.38877(12) 0.6131(2) 0.0410(4) Uani 1 1 d D . . . . C9 C 0.1296(7) 0.3636(8) 0.6060(15) 0.059(3) Uani 0.741(4) 1 d D . P B 1 H9 H 0.073307 0.367113 0.503990 0.071 Uiso 0.741(4) 1 calc R . P B 1 C9A C 0.2867(16) 0.3631(17) 0.777(3) 0.165(17) Uani 0.259(4) 1 d D . P B 2 H9A H 0.358859 0.374626 0.821492 0.198 Uiso 0.259(4) 1 calc R . P B 2 C10 C 0.1182(7) 0.3315(6) 0.7674(12) 0.054(2) Uani 0.741(4) 1 d D . P B 1 H10 H 0.054312 0.313641 0.784824 0.065 Uiso 0.741(4) 1 calc R . P B 1 C10A C 0.2290(19) 0.318(2) 0.877(3) 0.058(7) Uani 0.259(4) 1 d D . P B 2 H10A H 0.256962 0.295586 0.990025 0.070 Uiso 0.259(4) 1 calc R . P B 2 C11 C 0.2112(7) 0.3304(8) 0.8903(13) 0.060(2) Uani 0.741(4) 1 d D . P B 1 H11 H 0.220214 0.311385 1.005092 0.072 Uiso 0.741(4) 1 calc R . P B 1 C11A C 0.1287(18) 0.3124(16) 0.782(3) 0.044(4) Uani 0.259(4) 1 d D . P B 2 H11A H 0.076605 0.283796 0.819322 0.052 Uiso 0.259(4) 1 calc R . P B 2 C12 C 0.50938(15) 0.37347(15) 0.3091(3) 0.0550(5) Uani 1 1 d D . . . . C13 C 0.11749(14) 0.56873(13) 0.0041(2) 0.0500(5) Uani 1 1 d . . . . . H13A H 0.075000 0.540867 0.070836 0.060 Uiso 1 1 calc R . . . . H13B H 0.125234 0.527554 -0.084931 0.060 Uiso 1 1 calc R . . . . C14 C 0.06352(15) 0.65097(15) -0.0818(2) 0.0581(5) Uani 1 1 d . . . . . H14A H -0.006011 0.636058 -0.158557 0.070 Uiso 1 1 calc R . . . . H14B H 0.053799 0.690874 0.007781 0.070 Uiso 1 1 calc R . . . . C15 C 0.22463(16) 0.71564(14) -0.0680(2) 0.0606(6) Uani 1 1 d . . . . . H15A H 0.216487 0.756327 0.021553 0.073 Uiso 1 1 calc R . . . . H15B H 0.265758 0.744868 -0.135393 0.073 Uiso 1 1 calc R . . . . C16 C 0.28327(14) 0.63510(14) 0.0189(2) 0.0516(5) Uani 1 1 d . . . . . H16A H 0.294394 0.595172 -0.069607 0.062 Uiso 1 1 calc R . . . . H16B H 0.352057 0.651893 0.095772 0.062 Uiso 1 1 calc R . . . . 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 0.0407(8) 0.0286(9) 0.0384(8) -0.0025(7) 0.0104(7) -0.0035(7) N1 0.0416(7) 0.0343(8) 0.0404(7) 0.0040(6) 0.0114(6) -0.0027(6) O1 0.0709(8) 0.0657(10) 0.0456(7) 0.0167(6) 0.0114(7) -0.0005(7) F1 0.0518(17) 0.072(3) 0.168(5) -0.033(4) 0.056(2) -0.017(2) S1 0.0718(7) 0.0634(6) 0.0476(5) 0.0158(4) 0.0119(4) -0.0044(5) F1A 0.042(2) 0.163(8) 0.097(6) -0.065(7) -0.018(3) 0.030(4) S1A 0.043(2) 0.0489(19) 0.055(2) 0.0038(15) 0.024(2) -0.0028(13) C2 0.0421(8) 0.0423(11) 0.0433(8) -0.0012(7) 0.0164(7) -0.0029(8) F2 0.100(4) 0.190(6) 0.124(5) 0.087(5) 0.060(4) 0.097(4) F2A 0.067(4) 0.079(5) 0.229(15) -0.087(8) 0.022(8) 0.007(4) C3 0.0392(8) 0.0401(11) 0.0489(9) -0.0054(8) 0.0126(7) 0.0041(8) F3 0.064(2) 0.114(6) 0.112(3) -0.068(3) 0.010(2) 0.030(3) F3A 0.132(8) 0.180(12) 0.244(12) 0.117(8) 0.150(8) 0.086(7) C4 0.0457(9) 0.0354(10) 0.0494(9) 0.0039(8) 0.0130(8) 0.0046(8) C5 0.0414(8) 0.0318(9) 0.0406(8) -0.0012(7) 0.0120(7) -0.0011(7) C6 0.0394(8) 0.0284(9) 0.0402(8) -0.0020(7) 0.0124(7) 0.0002(7) C7 0.0555(10) 0.0373(10) 0.0565(10) 0.0059(8) 0.0255(8) 0.0095(9) C8 0.0495(10) 0.0302(9) 0.0444(9) 0.0025(7) 0.0154(8) 0.0038(8) C9 0.066(7) 0.059(4) 0.053(3) 0.002(2) 0.019(4) 0.003(4) C9A 0.080(12) 0.17(2) 0.22(3) -0.001(19) 0.008(13) -0.045(12) C10 0.067(3) 0.031(5) 0.075(3) 0.007(2) 0.038(2) 0.004(2) C10A 0.071(8) 0.046(11) 0.056(11) 0.024(10) 0.015(7) 0.025(7) C11 0.100(5) 0.039(3) 0.050(3) 0.005(2) 0.037(3) 0.003(4) C11A 0.081(10) 0.010(7) 0.043(7) -0.001(4) 0.024(7) -0.003(6) C12 0.0458(10) 0.0552(14) 0.0660(13) -0.0027(11) 0.0194(10) 0.0074(10) C13 0.0486(9) 0.0465(11) 0.0492(9) 0.0055(9) 0.0050(8) -0.0076(9) C14 0.0546(11) 0.0606(14) 0.0557(11) 0.0146(10) 0.0103(9) 0.0016(10) C15 0.0705(12) 0.0550(13) 0.0558(11) 0.0159(10) 0.0172(10) -0.0082(11) C16 0.0533(10) 0.0517(12) 0.0525(10) 0.0089(9) 0.0192(9) -0.0058(9) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 '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 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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 C2 C1 N1 121.00(14) C2 C1 C6 120.12(14) C6 C1 N1 118.83(14) C1 N1 C13 113.87(13) C1 N1 C16 117.36(13) C13 N1 C16 109.14(13) C14 O1 C15 109.07(13) C8 S1 C11 92.9(3) C8 S1A C11A 93.8(9) C3 C2 C1 120.00(15) C2 C3 C12 119.38(16) C4 C3 C2 120.54(15) C4 C3 C12 120.02(16) C3 C4 C5 120.33(16) C4 C5 C6 120.26(15) C4 C5 C8 117.94(15) C6 C5 C8 121.77(15) C1 C6 C7 120.53(14) C5 C6 C1 118.54(14) C5 C6 C7 120.71(14) C5 C8 S1 120.06(14) C5 C8 S1A 124.4(3) C9 C8 S1 109.6(5) C9 C8 C5 130.2(5) C9A C8 S1A 108.4(9) C9A C8 C5 126.7(9) C8 C9 C10 114.3(8) C8 C9A C10A 116.1(16) C11 C10 C9 110.8(8) C11A C10A C9A 108(2) C10 C11 S1 112.3(7) C10A C11A S1A 113.2(19) F1 C12 F2 105.3(5) F1 C12 C3 114.2(3) F1A C12 F2A 102.5(8) F1A C12 C3 114.6(5) F1A C12 F3A 107.9(8) F2 C12 C3 112.8(3) F2A C12 C3 115.8(7) F2A C12 F3A 102.8(9) F3 C12 F1 106.3(6) F3 C12 F2 105.4(5) F3 C12 C3 112.2(5) F3A C12 C3 112.2(5) N1 C13 C14 109.19(15) O1 C14 C13 111.65(16) O1 C15 C16 111.50(17) N1 C16 C15 109.23(15) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 N1 1.421(2) C1 C2 1.392(2) C1 C6 1.411(2) N1 C13 1.456(2) N1 C16 1.457(2) O1 C14 1.416(2) O1 C15 1.419(2) F1 C12 1.300(5) S1 C8 1.680(2) S1 C11 1.701(9) F1A C12 1.254(8) S1A C8 1.646(8) S1A C11A 1.690(18) C2 C3 1.382(2) F2 C12 1.316(6) F2A C12 1.286(12) C3 C4 1.372(2) C3 C12 1.491(2) F3 C12 1.294(8) F3A C12 1.317(10) C4 C5 1.395(2) C5 C6 1.397(2) C5 C8 1.479(2) C6 C7 1.506(2) C8 C9 1.363(9) C8 C9A 1.359(17) C9 C10 1.418(12) C9A C10A 1.42(2) C10 C11 1.330(7) C10A C11A 1.323(15) C13 C14 1.500(3) C15 C16 1.504(3)