#------------------------------------------------------------------------------ #$Date: 2021-07-05 21:04:11 +0300 (Mon, 05 Jul 2021) $ #$Revision: 267211 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/06/06/7060614.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_7060614 loop_ _publ_author_name 'Li, Huizhen' 'Li, Yunhui' 'Kang, Jiaxin' 'Fan, Lin' 'Yang, Qiuyu' 'Li, Shujun' 'Rahman, Abdul' 'Chen, Daqi' _publ_section_title ; Reactivity and mechanisms of hydridic hydrogen of B--H in ammonia borane towards acetic acids: the ammonia B-monoacyloxy boranes ; _journal_issue 22 _journal_name_full 'New Journal of Chemistry' _journal_page_first 9904 _journal_page_last 9911 _journal_paper_doi 10.1039/D1NJ01727F _journal_volume 45 _journal_year 2021 _chemical_formula_sum 'C8 H18 B Cl2 N O5' _chemical_formula_weight 289.94 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens mixed _audit_update_record ; 2019-10-08 deposited with the CCDC. 2021-04-28 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 99.807(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.6163(11) _cell_length_b 11.9140(15) _cell_length_c 13.6933(16) _cell_measurement_reflns_used 8572 _cell_measurement_temperature 153.(2) _cell_measurement_theta_max 23.6691 _cell_measurement_theta_min 2.6074 _cell_volume 1385.1(3) _computing_cell_refinement 'SAINT V8.34A (Bruker AXS Inc., 2013)' _computing_data_collection 'APEX2 (Bruker AXS Inc., 2014)' _computing_data_reduction 'SAINT V8.34A (Bruker AXS Inc., 2013)' _computing_molecular_graphics 'XP (Bruker AXS Inc., 2014)' _computing_publication_material 'APEX2 (Bruker AXS Inc., 2014)' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXT (Bruker AXS Inc., 2014)' _diffrn_ambient_temperature 153.(2) _diffrn_detector_area_resol_mean 8.3333 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0703 _diffrn_reflns_av_unetI/netI 0.0865 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 13711 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_min 2.95 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 0.476 _exptl_absorpt_correction_T_max 0.90 _exptl_absorpt_correction_T_min 0.78 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2014/5 (Bruker AXS Inc.)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.390 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 608 _exptl_crystal_size_max 0.360 _exptl_crystal_size_mid 0.240 _exptl_crystal_size_min 0.220 _refine_diff_density_max 0.454 _refine_diff_density_min -0.459 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.910 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 313 _refine_ls_number_reflns 3186 _refine_ls_number_restraints 702 _refine_ls_restrained_S_all 0.855 _refine_ls_R_factor_all 0.1077 _refine_ls_R_factor_gt 0.0560 _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^)+(0.0682P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1280 _refine_ls_wR_factor_ref 0.1476 _reflns_number_gt 1698 _reflns_number_total 3186 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1nj01727f2.cif _cod_data_source_block I _cod_depositor_comments 'Adding full bibliography for 7060613--7060614.cif.' _cod_database_code 7060614 _shelx_res_file ; xn_9_5.res created by SHELXL-2014/7 TITL xn_9_5 in P2(1)/n CELL 0.71073 8.61630 11.91400 13.69329 90.0000 99.8074 90.0000 ZERR 4.00 0.00110 0.00150 0.00164 0.0000 0.0030 0.0000 LATT 1 SYMM 0.5-X, 0.5+Y, 0.5-Z SFAC C H B N O Cl UNIT 32 72 4 4 20 8 L.S. 12 ACTA omit 0 1 1 omit -1 0 1 BOND rigu sadi b1 h1b b1a h1ba b1 h2b b1a h2ba sadi h1b h2b h1ba h2ba FMAP 2 simu 0.02 C1 > O3a simu 0.02 B1 > N1 PLAN 20 sadi n1 b1 n1 b1a SIZE 0.220 0.240 0.360 TEMP -120 WGHT 0.068200 FVAR 0.24138 0.49223 0.58082 MOLE 1 part 1 31 C1 1 0.834636 0.567195 0.687972 31.00000 0.02078 0.03079 = 0.02971 -0.00533 -0.00572 -0.00660 AFIX 23 H1A 2 0.881594 0.576557 0.758678 31.00000 -1.20000 H1C 2 0.876264 0.627128 0.649519 31.00000 -1.20000 AFIX 0 C2 1 0.616146 0.677152 0.715087 31.00000 0.04299 0.02771 = 0.02987 -0.00936 0.00670 -0.00188 AFIX 23 H2A 2 0.644102 0.741749 0.676038 31.00000 -1.20000 H2C 2 0.668980 0.686836 0.784647 31.00000 -1.20000 AFIX 0 C3 1 0.442010 0.672327 0.710250 31.00000 0.03479 0.02901 = 0.02659 -0.00963 0.01297 -0.00111 AFIX 23 H3A 2 0.413970 0.606357 0.747621 31.00000 -1.20000 H3B 2 0.405362 0.740726 0.740514 31.00000 -1.20000 AFIX 0 C4 1 0.201178 0.656276 0.598848 31.00000 0.02630 0.01996 = 0.05151 -0.00077 0.02184 0.00239 AFIX 23 H4A 2 0.159260 0.721920 0.630264 31.00000 -1.20000 H4B 2 0.171982 0.587510 0.632045 31.00000 -1.20000 AFIX 0 C5 1 0.133002 0.652588 0.491668 31.00000 0.02509 0.02169 = 0.04613 0.00154 0.00922 0.00765 AFIX 23 H5A 2 0.016665 0.656379 0.482801 31.00000 -1.20000 H5B 2 0.170851 0.717489 0.457154 31.00000 -1.20000 AFIX 0 C6 1 0.123374 0.543841 0.347466 31.00000 0.02078 0.02399 = 0.04908 0.00661 -0.00266 -0.00218 AFIX 23 H6A 2 0.171352 0.603876 0.312437 31.00000 -1.20000 H6B 2 0.007615 0.553765 0.334171 31.00000 -1.20000 AFIX 0 O1 5 0.666496 0.575477 0.676043 31.00000 0.02920 0.02039 = 0.03022 -0.00839 0.00777 -0.00598 O2 5 0.367942 0.664262 0.609286 31.00000 0.02638 0.02536 = 0.02957 -0.00356 0.01288 -0.00002 O3 5 0.180294 0.550345 0.451056 31.00000 0.02433 0.01773 = 0.04272 0.00148 0.00332 0.00566 part 2 -31 same c1 > O3 C1A 1 0.778745 0.607767 0.706149 -31.00000 0.03435 0.03506 = 0.02225 0.00016 -0.00061 -0.01777 AFIX 23 H1A1 2 0.810717 0.628867 0.776636 -31.00000 -1.20000 H1A2 2 0.812776 0.667893 0.664574 -31.00000 -1.20000 AFIX 0 C2A 1 0.528355 0.689748 0.707721 -31.00000 0.04061 0.02782 = 0.02888 -0.01682 0.00368 -0.00263 AFIX 23 H2A1 2 0.555440 0.755445 0.669663 -31.00000 -1.20000 H2A2 2 0.558466 0.706749 0.779210 -31.00000 -1.20000 AFIX 0 C3A 1 0.356129 0.667666 0.683642 -31.00000 0.03806 0.02168 = 0.03703 -0.00400 0.01174 0.00521 AFIX 23 H3A1 2 0.329805 0.599454 0.718747 -31.00000 -1.20000 H3A2 2 0.297253 0.731666 0.705503 -31.00000 -1.20000 AFIX 0 C4A 1 0.147519 0.642471 0.548051 -31.00000 0.02147 0.03143 = 0.04515 0.00029 0.00618 0.00255 AFIX 23 H4A1 2 0.094332 0.711199 0.566093 -31.00000 -1.20000 H4A2 2 0.107278 0.577821 0.581691 -31.00000 -1.20000 AFIX 0 C5A 1 0.114017 0.626271 0.441086 -31.00000 0.02912 0.03653 = 0.04468 0.00618 -0.00084 0.00348 AFIX 23 H5A1 2 -0.001151 0.628312 0.417576 -31.00000 -1.20000 H5A2 2 0.162916 0.687279 0.407724 -31.00000 -1.20000 AFIX 0 C6A 1 0.146542 0.501785 0.314138 -31.00000 0.02550 0.03782 = 0.03412 0.00630 -0.00334 0.00395 AFIX 23 H6A1 2 0.191766 0.563595 0.279633 -31.00000 -1.20000 H6A2 2 0.031703 0.498920 0.289554 -31.00000 -1.20000 AFIX 0 O1A 5 0.611679 0.593934 0.683426 -31.00000 0.03382 0.02311 = 0.02648 -0.01120 0.00013 -0.00796 O2A 5 0.312495 0.652456 0.578890 -31.00000 0.02403 0.02575 = 0.03782 -0.00320 0.00926 -0.00011 O3A 5 0.175562 0.520768 0.417526 -31.00000 0.02867 0.02813 = 0.03318 0.01048 0.00242 0.00096 part 1 21 B1 3 0.367909 0.331281 0.646567 21.00000 0.02061 0.01433 = 0.02260 -0.00131 0.00715 0.00273 H1B 2 0.286374 0.392374 0.678205 21.00000 -1.50000 H2B 2 0.466787 0.296141 0.705520 21.00000 -1.50000 C7 1 0.224423 0.060865 0.518969 21.00000 0.03674 0.02035 = 0.03943 -0.00263 0.01086 -0.00419 AFIX 13 H7 2 0.127004 0.074704 0.547765 21.00000 -1.20000 AFIX 0 C8 1 0.344453 0.152895 0.556691 21.00000 0.03157 0.01929 = 0.02502 -0.00046 0.00730 0.00192 CL1 6 0.299727 -0.070659 0.559749 21.00000 0.05972 0.02963 = 0.18714 0.03808 0.02283 -0.00174 CL2 6 0.176074 0.070676 0.391938 21.00000 0.10669 0.09325 = 0.05228 -0.00809 -0.01492 -0.06633 O4 5 0.273715 0.234874 0.594835 21.00000 0.01954 0.01058 = 0.02392 -0.00104 0.00965 -0.00237 O5 5 0.481433 0.149172 0.548660 21.00000 0.02708 0.02656 = 0.05650 -0.01994 0.01625 0.00075 PART 2 -21.00 same b1 > O5 B1A 3 0.436950 0.311650 0.656010 -21.00000 0.04170 0.01922 = 0.02107 -0.00220 0.00778 -0.00391 H1BA 2 0.551549 0.312487 0.713430 -21.00000 -1.50000 H2BA 2 0.329602 0.341602 0.686837 -21.00000 0.03577 C7A 1 0.298708 0.045582 0.517882 -21.00000 0.03104 0.01714 = 0.02984 -0.00058 0.00947 -0.00007 AFIX 13 H7A 2 0.406318 0.023213 0.507000 -21.00000 -1.20000 AFIX 0 C8A 1 0.301906 0.170264 0.546756 -21.00000 0.02182 0.02314 = 0.02665 0.00552 0.00517 -0.00346 CL1A 6 0.250985 -0.032844 0.618780 -21.00000 0.06931 0.01341 = 0.04007 0.00146 0.02291 -0.00678 CL2A 6 0.164359 0.017957 0.409524 -21.00000 0.05886 0.04436 = 0.04090 -0.01750 -0.00230 -0.01410 O4A 5 0.423146 0.193833 0.611022 -21.00000 0.03959 0.02222 = 0.03782 0.00365 -0.00462 -0.00836 O5A 5 0.201337 0.235224 0.508584 -21.00000 0.03795 0.02913 = 0.07279 0.00349 -0.00780 0.00383 part 0 N1 4 0.446726 0.399653 0.568177 11.00000 0.02635 0.01629 = 0.02320 -0.00077 0.00500 -0.00302 part 1 21 AFIX 3 H3N 2 0.499509 0.356696 0.536206 21.00000 -1.50000 H2N 2 0.508385 0.450194 0.597008 21.00000 -1.50000 H1N 2 0.375710 0.432426 0.525658 21.00000 -1.50000 AFIX 3 part 2 -21 H3NA 2 0.515162 0.375971 0.533239 -21.00000 -1.50000 H2NA 2 0.478392 0.462780 0.592542 -21.00000 -1.50000 H1NA 2 0.359696 0.406467 0.530117 -21.00000 -1.50000 part 0 AFIX 0 HKLF 4 REM xn_9_5 in P2(1)/n REM R1 = 0.0560 for 1698 Fo > 4sig(Fo) and 0.1077 for all 3186 data REM 313 parameters refined using 702 restraints END WGHT 0.0683 0.0000 REM Highest difference peak 0.454, deepest hole -0.459, 1-sigma level 0.059 Q1 1 0.1102 0.0931 0.4448 11.00000 0.05 0.45 Q2 1 0.2660 0.0110 0.4000 11.00000 0.05 0.33 Q3 1 0.1638 0.0011 0.6141 11.00000 0.05 0.30 Q4 1 0.2895 -0.0345 0.6062 11.00000 0.05 0.19 Q5 1 0.5524 0.6227 0.6950 11.00000 0.05 0.19 Q6 1 0.6998 0.5144 0.7391 11.00000 0.05 0.18 Q7 1 0.4518 0.7123 0.8008 11.00000 0.05 0.17 Q8 1 0.5437 0.1789 0.5587 11.00000 0.05 0.17 Q9 1 0.1711 0.1056 0.3800 11.00000 0.05 0.17 Q10 1 0.6798 0.6195 0.8341 11.00000 0.05 0.17 Q11 1 0.8228 0.6456 0.8823 11.00000 0.05 0.16 Q12 1 0.9655 0.6715 0.7797 11.00000 0.05 0.16 Q13 1 -0.0332 0.6342 0.2442 11.00000 0.05 0.16 Q14 1 -0.0241 0.6606 0.3741 11.00000 0.05 0.15 Q15 1 0.8653 0.6027 0.7223 11.00000 0.05 0.15 Q16 1 0.3221 0.4558 0.7634 11.00000 0.05 0.15 Q17 1 0.5068 0.4679 0.7416 11.00000 0.05 0.15 Q18 1 0.1431 0.0825 0.3643 11.00000 0.05 0.15 Q19 1 0.1237 0.3742 0.6648 11.00000 0.05 0.15 Q20 1 -0.0020 0.6418 0.3580 11.00000 0.05 0.15 ; _shelx_res_checksum 81995 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_refinement_flags_posn _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C C1 0.8346(8) 0.5672(6) 0.6880(5) 0.0283(14) Uani d U P D 0.581(7) A 1 H H1A 0.8816 0.5766 0.7587 0.034 Uiso calc U P R 0.581(7) A 1 H H1C 0.8763 0.6271 0.6495 0.034 Uiso calc U P R 0.581(7) A 1 C C2 0.6161(9) 0.6772(5) 0.7151(4) 0.0335(13) Uani d U P D 0.581(7) A 1 H H2A 0.6441 0.7417 0.676 0.04 Uiso calc U P R 0.581(7) A 1 H H2C 0.669 0.6868 0.7846 0.04 Uiso calc U P R 0.581(7) A 1 C C3 0.4420(9) 0.6723(5) 0.7102(4) 0.0292(14) Uani d U P D 0.581(7) A 1 H H3A 0.414 0.6064 0.7476 0.035 Uiso calc U P R 0.581(7) A 1 H H3B 0.4054 0.7407 0.7405 0.035 Uiso calc U P R 0.581(7) A 1 C C4 0.2012(8) 0.6563(4) 0.5988(5) 0.0308(13) Uani d U P D 0.581(7) A 1 H H4A 0.1593 0.7219 0.6303 0.037 Uiso calc U P R 0.581(7) A 1 H H4B 0.172 0.5875 0.632 0.037 Uiso calc U P R 0.581(7) A 1 C C5 0.1330(7) 0.6526(5) 0.4917(6) 0.0306(14) Uani d U P D 0.581(7) A 1 H H5A 0.0167 0.6564 0.4828 0.037 Uiso calc U P R 0.581(7) A 1 H H5B 0.1709 0.7175 0.4572 0.037 Uiso calc U P R 0.581(7) A 1 C C6 0.1234(7) 0.5438(6) 0.3475(6) 0.0323(14) Uani d U P D 0.581(7) A 1 H H6A 0.1714 0.6039 0.3124 0.039 Uiso calc U P R 0.581(7) A 1 H H6B 0.0076 0.5538 0.3342 0.039 Uiso calc U P R 0.581(7) A 1 O O1 0.6665(7) 0.5755(5) 0.6760(5) 0.0263(12) Uani d U P D 0.581(7) A 1 O O2 0.3679(6) 0.6643(4) 0.6093(4) 0.0262(11) Uani d U P D 0.581(7) A 1 O O3 0.1803(7) 0.5503(5) 0.4511(4) 0.0285(12) Uani d U P D 0.581(7) A 1 C C1A 0.7787(12) 0.6078(8) 0.7061(6) 0.0312(19) Uani d U P D 0.419(7) A 2 H H1A1 0.8107 0.6289 0.7766 0.037 Uiso calc U P R 0.419(7) A 2 H H1A2 0.8128 0.6679 0.6646 0.037 Uiso calc U P R 0.419(7) A 2 C C2A 0.5284(13) 0.6897(7) 0.7077(6) 0.033(2) Uani d U P D 0.419(7) A 2 H H2A1 0.5554 0.7554 0.6697 0.039 Uiso calc U P R 0.419(7) A 2 H H2A2 0.5585 0.7067 0.7792 0.039 Uiso calc U P R 0.419(7) A 2 C C3A 0.3561(11) 0.6677(6) 0.6836(7) 0.0316(18) Uani d U P D 0.419(7) A 2 H H3A1 0.3298 0.5995 0.7187 0.038 Uiso calc U P R 0.419(7) A 2 H H3A2 0.2973 0.7317 0.7055 0.038 Uiso calc U P R 0.419(7) A 2 C C4A 0.1475(10) 0.6425(7) 0.5481(8) 0.033(2) Uani d U P D 0.419(7) A 2 H H4A1 0.0943 0.7112 0.5661 0.039 Uiso calc U P R 0.419(7) A 2 H H4A2 0.1073 0.5778 0.5817 0.039 Uiso calc U P R 0.419(7) A 2 C C5A 0.1140(10) 0.6263(8) 0.4411(7) 0.038(2) Uani d U P D 0.419(7) A 2 H H5A1 -0.0012 0.6283 0.4176 0.045 Uiso calc U P R 0.419(7) A 2 H H5A2 0.1629 0.6873 0.4077 0.045 Uiso calc U P R 0.419(7) A 2 C C6A 0.1465(11) 0.5018(10) 0.3141(7) 0.033(2) Uani d U P D 0.419(7) A 2 H H6A1 0.1918 0.5636 0.2796 0.04 Uiso calc U P R 0.419(7) A 2 H H6A2 0.0317 0.4989 0.2896 0.04 Uiso calc U P R 0.419(7) A 2 O O1A 0.6117(9) 0.5939(7) 0.6834(7) 0.0284(17) Uani d U P D 0.419(7) A 2 O O2A 0.3125(9) 0.6525(6) 0.5789(5) 0.0287(15) Uani d U P D 0.419(7) A 2 O O3A 0.1756(10) 0.5208(7) 0.4175(6) 0.0303(16) Uani d U P D 0.419(7) A 2 B B1 0.3679(9) 0.3313(6) 0.6466(5) 0.0188(16) Uani d U P D 0.492(3) B 1 H H1B 0.286(5) 0.392(4) 0.678(3) 0.028 Uiso d U P D 0.492(3) B 1 H H2B 0.467(5) 0.296(4) 0.706(3) 0.028 Uiso d U P D 0.492(3) B 1 C C7 0.2244(8) 0.0609(5) 0.5190(5) 0.0317(16) Uani d U P D 0.492(3) B 1 H H7 0.127 0.0747 0.5478 0.038 Uiso calc U P R 0.492(3) B 1 C C8 0.3445(10) 0.1529(6) 0.5567(7) 0.0250(18) Uani d U P D 0.492(3) B 1 Cl Cl1 0.2997(3) -0.07066(17) 0.5597(3) 0.0920(11) Uani d U P D 0.492(3) B 1 Cl Cl2 0.1761(4) 0.0707(3) 0.3919(2) 0.0874(11) Uani d U P D 0.492(3) B 1 O O4 0.2737(4) 0.2349(3) 0.5948(2) 0.0173(8) Uani d U P D 0.492(3) B 1 O O5 0.4814(4) 0.1492(3) 0.5487(3) 0.0356(10) Uani d U P D 0.492(3) B 1 B B1A 0.4369(11) 0.3116(6) 0.6560(5) 0.0270(18) Uani d U P D 0.508(3) B 2 H H1BA 0.552(4) 0.312(4) 0.713(3) 0.041 Uiso d U P D 0.508(3) B 2 H H2BA 0.330(4) 0.342(4) 0.687(3) 0.036(18) Uiso d . P D 0.508(3) B 2 C C7A 0.2987(7) 0.0456(5) 0.5179(4) 0.0255(14) Uani d U P D 0.508(3) B 2 H H7A 0.4063 0.0232 0.507 0.031 Uiso calc U P R 0.508(3) B 2 C C8A 0.3019(9) 0.1703(6) 0.5468(7) 0.0237(17) Uani d U P D 0.508(3) B 2 Cl Cl1A 0.2510(2) -0.03284(12) 0.61878(10) 0.0393(5) Uani d U P D 0.508(3) B 2 Cl Cl2A 0.1644(3) 0.01796(19) 0.40952(17) 0.0493(6) Uani d U P D 0.508(3) B 2 O O4A 0.4231(4) 0.1938(3) 0.6110(3) 0.0345(10) Uani d U P D 0.508(3) B 2 O O5A 0.2013(4) 0.2352(3) 0.5086(3) 0.0486(12) Uani d U P D 0.508(3) B 2 N N1 0.4467(2) 0.39965(15) 0.56818(13) 0.0219(5) Uani d U . D 1.0 . . H H3N 0.4995 0.3567 0.5362 0.033 Uiso d U P R 0.492(3) B 1 H H2N 0.5084 0.4502 0.597 0.033 Uiso d U P R 0.492(3) B 1 H H1N 0.3757 0.4324 0.5257 0.033 Uiso d U P R 0.492(3) B 1 H H3NA 0.5152 0.376 0.5332 0.033 Uiso d U P R 0.508(3) B 2 H H2NA 0.4784 0.4628 0.5925 0.033 Uiso d U P R 0.508(3) B 2 H H1NA 0.3597 0.4065 0.5301 0.033 Uiso d U P R 0.508(3) B 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 C1 0.021(3) 0.031(4) 0.030(3) -0.007(3) -0.006(2) -0.005(3) C2 0.043(3) 0.028(3) 0.030(3) -0.002(3) 0.007(2) -0.009(2) C3 0.035(4) 0.029(3) 0.027(3) -0.001(3) 0.013(3) -0.010(2) C4 0.026(3) 0.020(2) 0.052(3) 0.002(2) 0.022(2) -0.001(2) C5 0.025(3) 0.022(3) 0.046(4) 0.008(2) 0.009(3) 0.002(3) C6 0.021(3) 0.024(3) 0.049(4) -0.002(2) -0.003(3) 0.007(3) O1 0.029(3) 0.020(2) 0.030(2) -0.006(2) 0.008(2) -0.0084(16) O2 0.026(3) 0.025(2) 0.030(3) 0.0000(19) 0.0129(18) -0.0036(18) O3 0.024(2) 0.018(2) 0.043(3) 0.0057(19) 0.003(2) 0.0015(18) C1A 0.034(4) 0.035(5) 0.022(3) -0.018(4) -0.001(3) 0.000(3) C2A 0.041(5) 0.028(4) 0.029(3) -0.003(4) 0.004(4) -0.017(3) C3A 0.038(4) 0.022(3) 0.037(4) 0.005(3) 0.012(3) -0.004(3) C4A 0.021(3) 0.031(4) 0.045(5) 0.003(3) 0.006(3) 0.000(4) C5A 0.029(4) 0.037(4) 0.045(4) 0.003(3) -0.001(3) 0.006(3) C6A 0.026(4) 0.038(6) 0.034(4) 0.004(4) -0.003(3) 0.006(4) O1A 0.034(4) 0.023(3) 0.026(3) -0.008(3) 0.000(3) -0.011(2) O2A 0.024(3) 0.026(3) 0.038(3) 0.000(3) 0.009(2) -0.003(2) O3A 0.029(3) 0.028(4) 0.033(4) 0.001(3) 0.002(3) 0.010(3) B1 0.021(4) 0.014(3) 0.023(3) 0.003(3) 0.007(3) -0.001(2) C7 0.037(4) 0.020(3) 0.039(3) -0.004(3) 0.011(3) -0.003(2) C8 0.032(4) 0.019(3) 0.025(3) 0.002(3) 0.007(3) 0.000(3) Cl1 0.0597(13) 0.0296(11) 0.187(3) -0.0017(9) 0.0228(15) 0.0381(15) Cl2 0.107(2) 0.093(2) 0.0523(13) -0.066(2) -0.0149(12) -0.0081(14) O4 0.0195(18) 0.0106(16) 0.0239(17) -0.0024(13) 0.0097(14) -0.0010(13) O5 0.027(2) 0.027(2) 0.057(2) 0.0007(16) 0.0162(17) -0.0199(18) B1A 0.042(5) 0.019(3) 0.021(3) -0.004(3) 0.008(3) -0.002(2) C7A 0.031(3) 0.017(3) 0.030(3) 0.000(3) 0.009(3) -0.0006(19) C8A 0.022(3) 0.023(3) 0.027(3) -0.003(2) 0.005(3) 0.006(2) Cl1A 0.0693(12) 0.0134(7) 0.0401(8) -0.0068(7) 0.0229(7) 0.0015(5) Cl2A 0.0589(13) 0.0444(13) 0.0409(10) -0.0141(11) -0.0023(8) -0.0175(9) O4A 0.040(2) 0.0222(19) 0.038(2) -0.0084(17) -0.0046(18) 0.0036(15) O5A 0.038(2) 0.029(2) 0.073(3) 0.0038(18) -0.008(2) 0.0035(19) N1 0.0263(11) 0.0163(10) 0.0232(10) -0.0030(9) 0.0050(8) -0.0008(8) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' B B 0.0013 0.0007 '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' Cl Cl 0.1484 0.1585 '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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O1 C1 C6 . 3_666 108.9(5) ? O1 C2 C3 . . 108.6(5) ? O2 C3 C2 . . 109.1(4) ? O2 C4 C5 . . 108.9(4) ? O3 C5 C4 . . 108.6(4) ? O3 C6 C1 . 3_666 108.3(5) ? C2 O1 C1 . . 112.5(5) ? C4 O2 C3 . . 112.3(5) ? C6 O3 C5 . . 111.2(5) ? O1A C1A C6A . 3_666 107.9(7) ? O1A C2A C3A . . 109.4(7) ? O2A C3A C2A . . 109.0(6) ? O2A C4A C5A . . 109.1(7) ? O3A C5A C4A . . 109.1(7) ? O3A C6A C1A . 3_666 108.4(7) ? C2A O1A C1A . . 112.8(7) ? C4A O2A C3A . . 112.8(7) ? C6A O3A C5A . . 111.1(7) ? O4 B1 N1 . . 109.3(5) ? C8 C7 Cl2 . . 108.9(6) ? C8 C7 Cl1 . . 109.9(5) ? Cl2 C7 Cl1 . . 113.3(4) ? O5 C8 O4 . . 126.5(6) ? O5 C8 C7 . . 123.9(7) ? O4 C8 C7 . . 109.6(7) ? C8 O4 B1 . . 120.4(5) ? O4A B1A N1 . . 107.9(4) ? C8A C7A Cl2A . . 112.3(5) ? C8A C7A Cl1A . . 107.8(5) ? Cl2A C7A Cl1A . . 110.7(3) ? O5A C8A O4A . . 126.7(6) ? O5A C8A C7A . . 121.8(6) ? O4A C8A C7A . . 111.5(6) ? C8A O4A B1A . . 118.5(5) ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 O1 . 1.433(7) ? C1 C6 3_666 1.475(8) ? C2 O1 . 1.421(6) ? C2 C3 . 1.492(7) ? C3 O2 . 1.424(6) ? C4 O2 . 1.423(6) ? C4 C5 . 1.486(8) ? C5 O3 . 1.427(6) ? C6 O3 . 1.422(7) ? C6 C1 3_666 1.475(8) ? C1A O1A . 1.430(9) ? C1A C6A 3_666 1.502(11) ? C2A O1A . 1.418(9) ? C2A C3A . 1.488(10) ? C3A O2A . 1.431(9) ? C4A O2A . 1.417(9) ? C4A C5A . 1.457(10) ? C5A O3A . 1.422(9) ? C6A O3A . 1.413(9) ? C6A C1A 3_666 1.502(11) ? B1 O4 . 1.511(7) ? B1 N1 . 1.589(7) ? C7 C8 . 1.535(9) ? C7 Cl2 . 1.722(7) ? C7 Cl1 . 1.751(7) ? C8 O5 . 1.205(9) ? C8 O4 . 1.306(8) ? B1A O4A . 1.529(7) ? B1A N1 . 1.609(7) ? C7A C8A . 1.536(8) ? C7A Cl2A . 1.751(6) ? C7A Cl1A . 1.773(6) ? C8A O5A . 1.212(8) ? C8A O4A . 1.277(8) ?