#------------------------------------------------------------------------------ #$Date: 2018-05-16 14:44:57 +0300 (Wed, 16 May 2018) $ #$Revision: 207805 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/54/94/1549415.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_1549415 loop_ _publ_author_name 'Shiro, Tomoya' 'Schuhmacher, Anne' 'Jackl, Moritz' 'Bode, Jeffrey W.' _publ_section_title ; Facile Synthesis of \a-Aminoboronic Acids from Amines and Potassium Acyltrifluoroborates (KATs) via Trifluoroborate-Iminiums (TIMs) ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/C8SC01486H _journal_year 2018 _chemical_formula_moiety 'C8 H8 B F4 N' _chemical_formula_sum 'C8 H8 B F4 N' _chemical_formula_weight 204.96 _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' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _audit_creation_date 2016-11-25 _audit_creation_method ; Olex2 1.2 (compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261) ; _audit_update_record ; 2018-03-29 deposited with the CCDC. 2018-05-14 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 93.529(3) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 6.1042(2) _cell_length_b 37.0556(10) _cell_length_c 7.9394(2) _cell_measurement_reflns_used 13847 _cell_measurement_temperature 100.0(1) _cell_measurement_theta_max 78.6570 _cell_measurement_theta_min 4.7500 _cell_volume 1792.45(9) _computing_cell_refinement 'CrysAlisPro 1.171.39.9f (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.39.9f (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.39.9f (Rigaku OD, 2015)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'XT (Sheldrick, 2015)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 100.0(1) _diffrn_detector 'CCD plate' _diffrn_detector_type 'Pilatus 300K' _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _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 -60.00 24.36 0.38 1.50 -- -50.21 19.00 -30.00 222 2 \w -121.00 -35.88 0.38 1.50 -- -50.21 -57.00 -30.00 224 3 \w -120.00 -39.06 0.38 1.50 -- -50.21-178.00-120.00 213 4 \w -76.00 3.80 0.38 9.00 -- -70.00 19.00 90.00 210 5 \w -140.00 -70.84 0.38 9.00 -- -70.00-125.00 60.00 182 6 \w 33.00 74.80 0.38 9.00 -- 107.75 -19.00 60.00 110 7 \w 33.00 68.72 0.38 9.00 -- 107.75 -38.00 -30.00 94 8 \w 33.00 74.80 0.38 9.00 -- 107.75 -19.00 -90.00 110 9 \w 39.00 110.06 0.38 9.00 -- 107.75 -99.00-120.00 187 10 \w 33.00 74.80 0.38 9.00 -- 107.75 -19.00 0.00 110 11 \w 33.00 68.72 0.38 9.00 -- 107.75 -38.00 60.00 94 12 \w 33.00 68.72 0.38 9.00 -- 107.75 -38.00 -60.00 94 13 \w 39.00 110.06 0.38 9.00 -- 107.75 -99.00-180.00 187 14 \w 37.00 105.02 0.38 9.00 -- 107.75 -57.00 120.00 179 15 \w 33.00 74.80 0.38 9.00 -- 107.75 -19.00 150.00 110 16 \w 33.00 68.72 0.38 9.00 -- 107.75 -38.00 150.00 94 17 \w 37.00 105.02 0.38 9.00 -- 107.75 -57.00 -90.00 179 18 \w 33.00 68.72 0.38 9.00 -- 107.75 -38.00 90.00 94 19 \w 37.00 105.02 0.38 9.00 -- 107.75 -57.00-150.00 179 20 \w 33.00 68.72 0.38 9.00 -- 107.75 -38.00-180.00 94 21 \w -121.00 -35.88 0.38 1.50 -- -50.21 -57.00 30.00 224 22 \w -115.00 -29.12 0.38 1.50 -- -50.21 -77.00 120.00 226 23 \w -115.00 -29.12 0.38 1.50 -- -50.21 -77.00 -90.00 226 24 \w -135.00 -47.98 0.38 9.00 -- -70.00 -77.00-150.00 229 25 \w -135.00 -47.98 0.38 9.00 -- -70.00 -77.00 -60.00 229 26 \w 97.00 177.18 0.38 9.00 -- 107.75 19.00 120.00 211 27 \w 98.00 168.68 0.38 9.00 -- 107.75 38.00 -30.00 186 28 \w 97.00 177.18 0.38 9.00 -- 107.75 19.00 60.00 211 29 \w 39.00 110.06 0.38 9.00 -- 107.75 -99.00 60.00 187 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy, Dualflex, Pilatus 300K' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0604759000 _diffrn_orient_matrix_UB_12 0.0266207000 _diffrn_orient_matrix_UB_13 0.1445977000 _diffrn_orient_matrix_UB_21 -0.0111635000 _diffrn_orient_matrix_UB_22 0.0315078000 _diffrn_orient_matrix_UB_23 -0.1265839000 _diffrn_orient_matrix_UB_31 -0.2453189000 _diffrn_orient_matrix_UB_32 0.0051166000 _diffrn_orient_matrix_UB_33 0.0291041000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_unetI/netI 0.0071 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 44 _diffrn_reflns_limit_k_min -44 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 6644 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 70.072 _diffrn_reflns_theta_min 4.774 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'PhotonJet (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 1.308 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.753 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.9f (Rigaku Oxford Diffraction, 2015) Numerical absorption correction based on gaussian integration over a multifaceted crystal model 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 1.519 _exptl_crystal_description plate _exptl_crystal_F_000 832 _exptl_crystal_size_max 0.141 _exptl_crystal_size_mid 0.121 _exptl_crystal_size_min 0.036 _refine_diff_density_max 0.428 _refine_diff_density_min -0.259 _refine_diff_density_rms 0.063 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.094 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 290 _refine_ls_number_reflns 6644 _refine_ls_number_restraints 89 _refine_ls_restrained_S_all 1.099 _refine_ls_R_factor_all 0.0692 _refine_ls_R_factor_gt 0.0653 _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^)+(0.1057P)^2^+0.9150P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1939 _refine_ls_wR_factor_ref 0.1980 _reflns_Friedel_coverage 0.000 _reflns_number_gt 6029 _reflns_number_total 6644 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c8sc01486h1.cif _cod_data_source_block jb211116_1_1 _cod_database_code 1549415 _chemical_oxdiff_formula 'C8 H8 B1 F4 N1' _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. ; _reflns_odcompleteness_completeness 99.94 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _olex2_refinement_description ; 1. Twinned data refinement Scales: 0.6815(17) 0.3185(17) 2. Fixed Uiso At 1.2 times of: All C(H) groups, All N(H) groups At 1.5 times of: All C(H,H,H) groups 3. Restrained distances N1A-H1A = N1B-H1B 0.93 with sigma of 0.02 F1C-B1B \\sim F1B-B1B \\sim F3C-B1B \\sim F3B-B1B \\sim F2C-B1B \\sim F2B-B1B with sigma of 0.02 F1B-F2B \\sim F2B-F3B \\sim F3B-F1B \\sim F1C-F2C \\sim F2C-F3C \\sim F3C-F1C with sigma of 0.02 4. Rigid body (RIGU) restrains F1B, F2B, F3B, B1B, F2C, F1C, F3C, C2B with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004 5. Others Sof(F2C)=Sof(F1C)=Sof(F3C)=1-FVAR(1) Sof(F1B)=Sof(F2B)=Sof(F3B)=FVAR(1) 6.a Aromatic/amide H refined with riding coordinates: C4A(H4A), C5A(H5A), C7A(H7A), C8A(H8A), C4B(H4B), C5B(H5B), C7B(H7B), C8B(H8B) 6.b Idealised Me refined as rotating group: C1A(H1AA,H1AB,H1AC), C1B(H1BA,H1BB,H1BC) ; _shelx_res_file ; jb211116_1_1.res created by SHELXL-2014/7 TITL jb211116_1_1_a.res in P2(1)/c REM Old TITL jb211116_1_1_twin1_hklf4 in P2(1)/c REM SHELXT solution in P2(1)/c REM R1 0.168, Rweak 0.010, Alpha 0.027, Orientation as input REM Formula found by SHELXT: C18 N2 F8 CELL 1.54184 6.1042 37.0556 7.9394 90 93.529 90 ZERR 8 0.0002 0.001 0.0002 0 0.003 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H B F N UNIT 64 64 8 32 8 DFIX 0.93 N1A H1A N1B H1B SADI F1C B1B F1B B1B F3C B1B F3B B1B F2C B1B F2B B1B SADI F1B F2B F2B F3B F3B F1B F1C F2C F2C F3C F3C F1C RIGU F1B F2B F3B B1B F2C F1C F3C C2B L.S. 10 PLAN 20 TEMP -173.15(10) BOND $H list 4 MORE -1 CONF fmap 2 ACTA SHEL 999 0.82 OMIT 1 -2 5 REM REM REM WGHT 0.105700 0.915000 BASF 0.31847 FVAR 5.19514 0.73033 F1A 4 1.195597 0.654292 0.220385 11.00000 0.03684 0.04013 = 0.04697 -0.00154 0.01094 0.00474 F2A 4 1.217855 0.678763 0.481014 11.00000 0.04254 0.06889 = 0.04136 -0.00532 0.00484 -0.01328 F3A 4 1.078963 0.711590 0.254286 11.00000 0.04473 0.03475 = 0.07158 0.00724 0.01961 0.00138 F4A 4 0.743155 0.512737 0.467954 11.00000 0.05441 0.02709 = 0.07644 0.00602 0.00872 0.00139 N1A 5 0.673790 0.680289 0.379955 11.00000 0.03282 0.03252 = 0.04078 0.00152 0.00847 0.00159 H1A 2 0.542912 0.669530 0.400706 11.00000 -1.20000 C1A 1 0.653180 0.719522 0.371749 11.00000 0.03894 0.03097 = 0.05954 0.00164 0.01008 0.00446 AFIX 137 H1AA 2 0.633657 0.727108 0.253529 11.00000 -1.50000 H1AB 2 0.786234 0.730656 0.423987 11.00000 -1.50000 H1AC 2 0.525817 0.727132 0.432223 11.00000 -1.50000 AFIX 0 C2A 1 0.846246 0.660855 0.363120 11.00000 0.03406 0.03480 = 0.03078 -0.00120 0.00297 0.00332 C3A 1 0.819506 0.621525 0.383419 11.00000 0.03297 0.03414 = 0.03415 0.00006 0.00639 0.00318 C4A 1 0.989204 0.601300 0.461969 11.00000 0.03313 0.03715 = 0.04329 -0.00082 0.00275 0.00252 AFIX 43 H4A 2 1.123956 0.612761 0.495969 11.00000 -1.20000 AFIX 0 C5A 1 0.964000 0.564762 0.491071 11.00000 0.04085 0.03682 = 0.04855 0.00403 0.00243 0.00823 AFIX 43 H5A 2 1.078650 0.551147 0.546888 11.00000 -1.20000 AFIX 0 C6A 1 0.769350 0.548606 0.437404 11.00000 0.04613 0.02875 = 0.04828 0.00029 0.01024 0.00283 C7A 1 0.599715 0.567207 0.355924 11.00000 0.03598 0.03657 = 0.05573 -0.00205 0.00550 0.00020 AFIX 43 H7A 2 0.467974 0.555198 0.318784 11.00000 -1.20000 AFIX 0 C8A 1 0.624697 0.603838 0.329025 11.00000 0.03264 0.03541 = 0.04575 -0.00139 0.00472 0.00334 AFIX 43 H8A 2 0.508694 0.617138 0.273141 11.00000 -1.20000 AFIX 0 B1A 3 1.091365 0.677847 0.326825 11.00000 0.03380 0.03285 = 0.04468 -0.00115 0.01016 0.00041 PART 1 F1B 4 0.716242 0.648507 1.003719 21.00000 0.03451 0.03967 = 0.04448 0.00068 0.00010 0.00065 F2B 4 0.677937 0.665620 0.730177 21.00000 0.03966 0.07149 = 0.04470 0.00563 0.01247 -0.01485 F3B 4 0.582155 0.703634 0.939027 21.00000 0.03823 0.03113 = 0.09932 -0.00204 -0.00038 -0.00277 PART 0 F4B 4 0.271470 0.499950 0.910154 11.00000 0.05513 0.02761 = 0.07136 0.00213 0.00898 -0.00394 N1B 5 0.157766 0.668307 0.847423 11.00000 0.03165 0.03127 = 0.04341 0.00020 0.00675 -0.00111 H1B 2 0.021306 0.657167 0.843610 11.00000 -1.20000 C1B 1 0.134104 0.707644 0.835216 11.00000 0.03726 0.03184 = 0.04928 -0.00005 0.00614 0.00368 AFIX 137 H1BA 2 0.001169 0.713531 0.765092 11.00000 -1.50000 H1BB 2 0.262368 0.717864 0.784079 11.00000 -1.50000 H1BC 2 0.122973 0.717808 0.948324 11.00000 -1.50000 AFIX 0 C2B 1 0.336731 0.649892 0.868566 11.00000 0.03365 0.03567 = 0.03104 -0.00024 0.00514 0.00114 C3B 1 0.314495 0.610334 0.879355 11.00000 0.03062 0.03453 = 0.03567 -0.00040 0.00079 -0.00094 C4B 1 0.473314 0.588235 0.811162 11.00000 0.03434 0.03329 = 0.04231 0.00023 0.00587 -0.00019 AFIX 43 H4B 2 0.593109 0.598949 0.758814 11.00000 -1.20000 AFIX 0 C5B 1 0.457637 0.550962 0.819205 11.00000 0.03962 0.03391 = 0.04921 -0.00214 0.00489 0.00182 AFIX 43 H5B 2 0.563140 0.535944 0.770818 11.00000 -1.20000 AFIX 0 C6B 1 0.284861 0.536358 0.899291 11.00000 0.04266 0.03114 = 0.04894 -0.00006 0.00090 -0.00266 C7B 1 0.126109 0.556894 0.969000 11.00000 0.04001 0.03779 = 0.05009 0.00215 0.00810 -0.00629 AFIX 43 H7B 2 0.009042 0.545824 1.023270 11.00000 -1.20000 AFIX 0 C8B 1 0.140972 0.594100 0.958197 11.00000 0.03330 0.03785 = 0.04196 -0.00193 0.00503 -0.00066 AFIX 43 H8B 2 0.032230 0.608751 1.004797 11.00000 -1.20000 AFIX 0 B1B 3 0.583740 0.668897 0.886296 11.00000 0.03232 0.03443 = 0.04079 0.00082 0.00337 -0.00290 PART 2 F2C 4 0.644765 0.680511 0.729570 -21.00000 0.05289 0.08250 = 0.04347 0.00711 0.00704 -0.01935 F1C 4 0.729657 0.645544 0.960697 -21.00000 0.03367 0.03186 = 0.07278 -0.00331 -0.00390 -0.00012 F3C 4 0.566014 0.700121 0.986654 -21.00000 0.04869 0.03033 = 0.05490 -0.01068 -0.00435 -0.00714 HKLF 5 REM jb211116_1_1_a.res in P2(1)/c REM R1 = 0.0653 for 6029 Fo > 4sig(Fo) and 0.0692 for all 6644 data REM 290 parameters refined using 89 restraints END WGHT 0.1063 0.9070 REM Highest difference peak 0.428, deepest hole -0.259, 1-sigma level 0.063 Q1 1 0.4568 0.6613 0.8815 11.00000 0.05 0.43 Q2 1 1.2130 0.6291 0.2286 11.00000 0.05 0.33 Q3 1 1.2357 0.6545 0.3405 11.00000 0.05 0.31 Q4 1 0.9539 0.6714 0.3366 11.00000 0.05 0.28 Q5 1 0.0839 0.7100 0.7157 11.00000 0.05 0.27 Q6 1 0.6876 0.5605 0.4210 11.00000 0.05 0.27 Q7 1 1.1717 0.7011 0.4795 11.00000 0.05 0.26 Q8 1 0.7000 0.6735 0.9911 11.00000 0.05 0.25 Q9 1 0.6868 0.6400 0.7464 11.00000 0.05 0.23 Q10 1 1.1230 0.7116 0.3582 11.00000 0.05 0.22 Q11 1 0.8452 0.6374 0.3717 11.00000 0.05 0.22 Q12 1 0.1945 0.5489 0.9091 11.00000 0.05 0.22 Q13 1 0.2724 0.4994 1.0256 11.00000 0.05 0.22 Q14 1 0.6732 0.6785 0.2788 11.00000 0.05 0.22 Q15 1 0.5590 0.7024 0.7967 11.00000 0.05 0.22 Q16 1 0.1326 0.6677 0.7363 11.00000 0.05 0.21 Q17 1 0.8656 0.6155 0.4458 11.00000 0.05 0.21 Q18 1 0.6017 0.6700 0.7608 11.00000 0.05 0.20 Q19 1 1.1974 0.6507 0.4882 11.00000 0.05 0.20 Q20 1 0.8469 0.5566 0.4799 11.00000 0.05 0.20 ; _shelx_res_checksum 13296 _shelx_shelxl_version_number 2014/7 _olex2_date_sample_data_collection 2016-11-22 _olex2_date_sample_submission 2016-11-21 _olex2_submission_original_sample_id jb211116_1_1 _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 - Detector area scaling ; _oxdiff_exptl_absorpt_empirical_full_max 2.312 _oxdiff_exptl_absorpt_empirical_full_min 0.619 _oxdiff_twin_integration_method simultaneous _oxdiff_twin_items 2 _twin_special_details ; Component 2 rotated by -179.9876\% around [1.00 -0.00 -0.00] (reciprocal) or [1.00 0.00 0.05] (direct) ; 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 F1A F 1.1956(3) 0.65429(4) 0.2204(2) 0.0410(4) Uani 1 1 d . . . . . F2A F 1.2179(3) 0.67876(5) 0.4810(2) 0.0508(5) Uani 1 1 d . . . . . F3A F 1.0790(3) 0.71159(4) 0.2543(2) 0.0497(5) Uani 1 1 d . . . . . F4A F 0.7432(3) 0.51274(4) 0.4680(3) 0.0525(5) Uani 1 1 d . . . . . N1A N 0.6738(4) 0.68029(6) 0.3800(3) 0.0351(5) Uani 1 1 d D . . . . H1A H 0.543(4) 0.6695(8) 0.401(4) 0.042 Uiso 1 1 d DR . . . . C1A C 0.6532(5) 0.71952(7) 0.3717(4) 0.0429(7) Uani 1 1 d . . . . . H1AA H 0.6337 0.7271 0.2535 0.064 Uiso 1 1 calc GR . . . . H1AB H 0.7862 0.7307 0.4240 0.064 Uiso 1 1 calc GR . . . . H1AC H 0.5258 0.7271 0.4322 0.064 Uiso 1 1 calc GR . . . . C2A C 0.8462(4) 0.66085(7) 0.3631(3) 0.0332(6) Uani 1 1 d . . . . . C3A C 0.8195(4) 0.62153(7) 0.3834(3) 0.0336(6) Uani 1 1 d . . . . . C4A C 0.9892(4) 0.60130(7) 0.4620(4) 0.0378(6) Uani 1 1 d . . . . . H4A H 1.1240 0.6128 0.4960 0.045 Uiso 1 1 calc R . . . . C5A C 0.9640(5) 0.56476(8) 0.4911(4) 0.0421(7) Uani 1 1 d . . . . . H5A H 1.0786 0.5511 0.5469 0.051 Uiso 1 1 calc R . . . . C6A C 0.7693(5) 0.54861(7) 0.4374(4) 0.0408(6) Uani 1 1 d . . . . . C7A C 0.5997(5) 0.56721(8) 0.3559(4) 0.0426(7) Uani 1 1 d . . . . . H7A H 0.4680 0.5552 0.3188 0.051 Uiso 1 1 calc R . . . . C8A C 0.6247(4) 0.60384(7) 0.3290(4) 0.0378(6) Uani 1 1 d . . . . . H8A H 0.5087 0.6171 0.2731 0.045 Uiso 1 1 calc R . . . . B1A B 1.0914(5) 0.67785(8) 0.3268(4) 0.0368(7) Uani 1 1 d . . . . . F1B F 0.7162(17) 0.6485(3) 1.0037(11) 0.0396(13) Uani 0.73(4) 1 d D U P A 1 F2B F 0.6779(11) 0.6656(3) 0.7302(6) 0.0515(17) Uani 0.73(4) 1 d D U P A 1 F3B F 0.5822(17) 0.70363(17) 0.9390(19) 0.0564(18) Uani 0.73(4) 1 d D U P A 1 F4B F 0.2715(3) 0.49995(4) 0.9102(3) 0.0512(5) Uani 1 1 d . . . . . N1B N 0.1578(4) 0.66831(6) 0.8474(3) 0.0353(5) Uani 1 1 d D . . . . H1B H 0.021(4) 0.6572(8) 0.844(4) 0.042 Uiso 1 1 d DR . . . . C1B C 0.1341(5) 0.70764(7) 0.8352(4) 0.0393(6) Uani 1 1 d . . . . . H1BA H 0.0012 0.7135 0.7651 0.059 Uiso 1 1 calc GR . . . . H1BB H 0.2624 0.7179 0.7841 0.059 Uiso 1 1 calc GR . . . . H1BC H 0.1230 0.7178 0.9483 0.059 Uiso 1 1 calc GR . . . . C2B C 0.3367(4) 0.64989(7) 0.8686(3) 0.0333(6) Uani 1 1 d . U . . . C3B C 0.3145(4) 0.61033(7) 0.8794(3) 0.0337(6) Uani 1 1 d . . . . . C4B C 0.4733(4) 0.58824(7) 0.8112(4) 0.0365(6) Uani 1 1 d . . . . . H4B H 0.5931 0.5989 0.7588 0.044 Uiso 1 1 calc R . . . . C5B C 0.4576(5) 0.55096(7) 0.8192(4) 0.0408(6) Uani 1 1 d . . . . . H5B H 0.5631 0.5359 0.7708 0.049 Uiso 1 1 calc R . . . . C6B C 0.2849(5) 0.53636(7) 0.8993(4) 0.0410(6) Uani 1 1 d . . . . . C7B C 0.1261(5) 0.55689(8) 0.9690(4) 0.0424(7) Uani 1 1 d . . . . . H7B H 0.0090 0.5458 1.0233 0.051 Uiso 1 1 calc R . . . . C8B C 0.1410(4) 0.59410(7) 0.9582(4) 0.0376(6) Uani 1 1 d . . . . . H8B H 0.0322 0.6088 1.0048 0.045 Uiso 1 1 calc R . . . . B1B B 0.5837(5) 0.66890(8) 0.8863(4) 0.0358(6) Uani 1 1 d D U . . . F2C F 0.645(4) 0.6805(11) 0.7296(15) 0.059(5) Uani 0.27(4) 1 d D U P A 2 F1C F 0.730(5) 0.6455(6) 0.961(4) 0.046(5) Uani 0.27(4) 1 d D U P A 2 F3C F 0.566(5) 0.7001(5) 0.987(3) 0.045(4) Uani 0.27(4) 1 d D U P A 2 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 F1A 0.0368(8) 0.0401(9) 0.0470(9) -0.0015(7) 0.0109(7) 0.0047(6) F2A 0.0425(10) 0.0689(12) 0.0414(10) -0.0053(8) 0.0048(7) -0.0133(8) F3A 0.0447(9) 0.0347(9) 0.0716(12) 0.0072(8) 0.0196(8) 0.0014(7) F4A 0.0544(11) 0.0271(8) 0.0764(13) 0.0060(8) 0.0087(9) 0.0014(7) N1A 0.0328(12) 0.0325(12) 0.0408(12) 0.0015(9) 0.0085(9) 0.0016(9) C1A 0.0389(15) 0.0310(14) 0.0595(18) 0.0016(12) 0.0101(13) 0.0045(11) C2A 0.0341(13) 0.0348(13) 0.0308(12) -0.0012(10) 0.0030(10) 0.0033(10) C3A 0.0330(13) 0.0341(13) 0.0341(13) 0.0001(10) 0.0064(10) 0.0032(10) C4A 0.0331(13) 0.0371(14) 0.0433(15) -0.0008(11) 0.0027(11) 0.0025(11) C5A 0.0409(15) 0.0368(14) 0.0485(16) 0.0040(12) 0.0024(12) 0.0082(11) C6A 0.0461(16) 0.0288(13) 0.0483(16) 0.0003(11) 0.0102(12) 0.0028(11) C7A 0.0360(14) 0.0366(15) 0.0557(17) -0.0021(12) 0.0055(12) 0.0002(11) C8A 0.0326(13) 0.0354(14) 0.0457(15) -0.0014(11) 0.0047(11) 0.0033(10) B1A 0.0338(15) 0.0329(15) 0.0447(17) -0.0012(12) 0.0102(13) 0.0004(11) F1B 0.0345(18) 0.040(2) 0.044(3) 0.0007(19) 0.0001(19) 0.0006(14) F2B 0.040(2) 0.071(4) 0.0447(16) 0.0056(17) 0.0125(12) -0.015(2) F3B 0.038(2) 0.0311(17) 0.099(5) -0.002(2) 0.000(3) -0.0028(13) F4B 0.0551(11) 0.0276(8) 0.0714(12) 0.0021(7) 0.0090(9) -0.0039(7) N1B 0.0316(11) 0.0313(11) 0.0434(13) 0.0002(9) 0.0068(9) -0.0011(9) C1B 0.0373(14) 0.0318(13) 0.0493(16) 0.0000(11) 0.0061(12) 0.0037(11) C2B 0.0336(13) 0.0357(13) 0.0310(12) -0.0002(10) 0.0051(10) 0.0011(10) C3B 0.0306(13) 0.0345(13) 0.0357(13) -0.0004(10) 0.0008(10) -0.0009(10) C4B 0.0343(13) 0.0333(13) 0.0423(15) 0.0002(11) 0.0059(11) -0.0002(10) C5B 0.0396(15) 0.0339(14) 0.0492(16) -0.0021(11) 0.0049(12) 0.0018(11) C6B 0.0427(15) 0.0311(14) 0.0489(16) -0.0001(11) 0.0009(12) -0.0027(11) C7B 0.0400(15) 0.0378(15) 0.0501(17) 0.0022(12) 0.0081(13) -0.0063(11) C8B 0.0333(13) 0.0378(14) 0.0420(15) -0.0019(11) 0.0050(11) -0.0007(11) B1B 0.0323(14) 0.0344(15) 0.0408(16) 0.0008(12) 0.0034(12) -0.0029(11) F2C 0.053(7) 0.083(12) 0.043(4) 0.007(5) 0.007(4) -0.019(7) F1C 0.034(5) 0.032(4) 0.073(11) -0.003(7) -0.004(8) 0.000(3) F3C 0.049(7) 0.030(5) 0.055(7) -0.011(4) -0.004(5) -0.007(4) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 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' B B 0.0090 0.0039 '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' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 2 5 0.0609 -3 3 -3 0.0729 0 23 1 0.0225 2 21 -1 0.0396 3 -9 2 0.0572 0 -11 5 0.0562 2 -19 1 0.0443 3 -16 -1 0.0661 -3 13 1 0.0535 0 24 0 0.0200 0 -24 0 0.0145 -1 -24 0 0.0235 -4 2 -1 0.0694 -4 3 1 0.0622 0 -2 -5 0.0596 4 -8 1 0.0612 4 -5 -1 0.0750 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C1A N1A H1A 112(2) C2A N1A H1A 120(2) C2A N1A C1A 128.3(2) N1A C1A H1AA 109.5 N1A C1A H1AB 109.5 N1A C1A H1AC 109.5 H1AA C1A H1AB 109.5 H1AA C1A H1AC 109.5 H1AB C1A H1AC 109.5 N1A C2A C3A 116.3(2) N1A C2A B1A 123.7(2) C3A C2A B1A 119.9(2) C4A C3A C2A 119.7(2) C4A C3A C8A 118.6(2) C8A C3A C2A 121.7(2) C3A C4A H4A 119.6 C5A C4A C3A 120.9(3) C5A C4A H4A 119.6 C4A C5A H5A 120.7 C6A C5A C4A 118.5(3) C6A C5A H5A 120.7 F4A C6A C5A 118.6(3) F4A C6A C7A 118.7(3) C7A C6A C5A 122.7(3) C6A C7A H7A 120.7 C6A C7A C8A 118.6(3) C8A C7A H7A 120.7 C3A C8A H8A 119.7 C7A C8A C3A 120.7(3) C7A C8A H8A 119.7 F1A B1A F2A 107.2(2) F1A B1A C2A 108.4(2) F2A B1A C2A 108.0(2) F3A B1A F1A 109.3(2) F3A B1A F2A 110.8(2) F3A B1A C2A 112.9(2) C1B N1B H1B 111(2) C2B N1B H1B 121(2) C2B N1B C1B 127.8(2) N1B C1B H1BA 109.5 N1B C1B H1BB 109.5 N1B C1B H1BC 109.5 H1BA C1B H1BB 109.5 H1BA C1B H1BC 109.5 H1BB C1B H1BC 109.5 N1B C2B C3B 116.9(2) N1B C2B B1B 122.9(2) C3B C2B B1B 120.2(2) C4B C3B C2B 119.3(2) C8B C3B C2B 121.9(2) C8B C3B C4B 118.8(2) C3B C4B H4B 119.6 C5B C4B C3B 120.8(3) C5B C4B H4B 119.6 C4B C5B H5B 121.0 C6B C5B C4B 118.1(3) C6B C5B H5B 121.0 F4B C6B C5B 118.2(3) F4B C6B C7B 118.6(3) C7B C6B C5B 123.2(3) C6B C7B H7B 120.8 C6B C7B C8B 118.4(3) C8B C7B H7B 120.8 C3B C8B H8B 119.7 C7B C8B C3B 120.7(3) C7B C8B H8B 119.7 F1B B1B C2B 108.0(5) F2B B1B F1B 106.7(4) F2B B1B C2B 107.9(3) F3B B1B F1B 108.6(5) F3B B1B F2B 111.5(4) F3B B1B C2B 113.9(5) F2C B1B C2B 110.3(8) F2C B1B F3C 106.6(11) F1C B1B C2B 109.6(14) F1C B1B F2C 112.6(11) F1C B1B F3C 110.4(13) F3C B1B C2B 107.1(12) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance F1A B1A 1.395(3) F2A B1A 1.407(4) F3A B1A 1.377(4) F4A C6A 1.362(3) N1A H1A 0.92(2) N1A C1A 1.460(3) N1A C2A 1.289(3) C1A H1AA 0.9800 C1A H1AB 0.9800 C1A H1AC 0.9800 C2A C3A 1.476(4) C2A B1A 1.665(4) C3A C4A 1.394(4) C3A C8A 1.402(4) C4A H4A 0.9500 C4A C5A 1.384(4) C5A H5A 0.9500 C5A C6A 1.375(4) C6A C7A 1.372(4) C7A H7A 0.9500 C7A C8A 1.384(4) C8A H8A 0.9500 F1B B1B 1.415(6) F2B B1B 1.403(5) F3B B1B 1.354(7) F4B C6B 1.355(3) N1B H1B 0.93(2) N1B C1B 1.467(3) N1B C2B 1.290(3) C1B H1BA 0.9800 C1B H1BB 0.9800 C1B H1BC 0.9800 C2B C3B 1.475(4) C2B B1B 1.662(4) C3B C4B 1.403(4) C3B C8B 1.399(4) C4B H4B 0.9500 C4B C5B 1.386(4) C5B H5B 0.9500 C5B C6B 1.376(4) C6B C7B 1.375(4) C7B H7B 0.9500 C7B C8B 1.385(4) C8B H8B 0.9500 B1B F2C 1.389(12) B1B F1C 1.351(15) B1B F3C 1.413(13) 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 F4A C6A C7A C8A 178.3(3) N1A C2A C3A C4A -143.2(3) N1A C2A C3A C8A 35.3(4) N1A C2A B1A F1A -144.5(3) N1A C2A B1A F2A 99.6(3) N1A C2A B1A F3A -23.2(4) C1A N1A C2A C3A 178.0(3) C1A N1A C2A B1A 0.0(4) C2A C3A C4A C5A 176.4(3) C2A C3A C8A C7A -177.2(3) C3A C2A B1A F1A 37.6(3) C3A C2A B1A F2A -78.3(3) C3A C2A B1A F3A 158.8(2) C3A C4A C5A C6A 1.4(4) C4A C3A C8A C7A 1.3(4) C4A C5A C6A F4A -179.1(3) C4A C5A C6A C7A 0.2(5) C5A C6A C7A C8A -1.0(5) C6A C7A C8A C3A 0.2(4) C8A C3A C4A C5A -2.2(4) B1A C2A C3A C4A 34.9(4) B1A C2A C3A C8A -146.6(3) F4B C6B C7B C8B 179.7(3) N1B C2B C3B C4B 145.0(3) N1B C2B C3B C8B -36.1(4) N1B C2B B1B F1B 144.0(5) N1B C2B B1B F2B -101.1(6) N1B C2B B1B F3B 23.3(8) N1B C2B B1B F2C -75.5(19) N1B C2B B1B F1C 160.0(16) N1B C2B B1B F3C 40.2(12) C1B N1B C2B C3B 179.1(2) C1B N1B C2B B1B 0.0(4) C2B C3B C4B C5B 179.9(2) C2B C3B C8B C7B -178.9(3) C3B C2B B1B F1B -35.1(5) C3B C2B B1B F2B 79.9(6) C3B C2B B1B F3B -155.8(7) C3B C2B B1B F2C 105.5(19) C3B C2B B1B F1C -19.1(16) C3B C2B B1B F3C -138.9(12) C3B C4B C5B C6B -1.5(4) C4B C3B C8B C7B 0.1(4) C4B C5B C6B F4B -178.8(2) C4B C5B C6B C7B 1.0(5) C5B C6B C7B C8B -0.1(5) C6B C7B C8B C3B -0.5(4) C8B C3B C4B C5B 0.9(4) B1B C2B C3B C4B -35.9(4) B1B C2B C3B C8B 143.0(3) loop_ _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z -0.3903 2.0111 5.0038 0.7535 -0.5657 0.2517 -2.8098 2.9957 -3.0037 -0.5245 0.5060 0.6172 0.3978 22.9856 0.9967 0.7801 0.5936 0.0490 1.7955 20.9798 -1.0043 0.5219 0.7681 -0.3623 3.4096 -8.9949 2.0041 0.2565 -0.5752 -0.8241 -0.1875 -10.9802 5.0062 0.4203 -0.9776 0.1355 2.2083 -18.9882 1.0048 -0.2266 -0.7501 -0.6096 3.0043 -15.9964 -0.9972 -0.3883 -0.4113 -0.8479 -3.2039 12.9988 0.9978 0.2965 0.3190 0.8815 -0.2051 23.9835 -0.0045 0.6254 0.7585 0.1729 0.0049 -23.9832 0.0044 -0.6375 -0.7563 -0.1238 -0.7959 -23.9818 0.0042 -0.6859 -0.7473 0.0727 -3.8065 2.0028 -1.0021 -0.3218 0.2324 0.9149 -4.0027 3.0072 0.9994 -0.0175 0.0129 1.0264 0.3903 -2.0111 -5.0038 -0.7535 0.5657 -0.2517 3.6075 -7.9983 1.0031 0.1503 -0.4193 -0.8967 3.8029 -5.0054 -0.9991 -0.0477 -0.0737 -0.9876 loop_ _twin_individual_id _twin_individual_mass_fraction_refined _oxdiff_twin_reflns_isolated _oxdiff_twin_reflns_overlapped _twin_individual_twin_lattice_type _twin_individual_twin_matrix_11 _twin_individual_twin_matrix_12 _twin_individual_twin_matrix_13 _twin_individual_twin_matrix_21 _twin_individual_twin_matrix_22 _twin_individual_twin_matrix_23 _twin_individual_twin_matrix_31 _twin_individual_twin_matrix_32 _twin_individual_twin_matrix_33 1 0.6815(17) 23983 1777 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000 0.0000 1.0000 2 0.3185(17) 24018 1777 nmt 0.9995 0.0000 0.0949 -0.0014 -0.9998 0.0114 -0.0006 -0.0000 -1.0002