#------------------------------------------------------------------------------ #$Date: 2021-04-29 06:42:17 +0300 (Thu, 29 Apr 2021) $ #$Revision: 264677 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/06/06/7060613.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_7060613 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_name_full 'New Journal of Chemistry' _journal_paper_doi 10.1039/D1NJ01727F _journal_year 2021 _chemical_formula_sum 'C8 H19 B Cl N O5' _chemical_formula_weight 255.50 _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_block_doi 10.5517/ccdc.csd.cc23qf2c _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2021-04-21 deposited with the CCDC. 2021-04-28 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 100.686(6) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.312(2) _cell_length_b 12.187(2) _cell_length_c 10.6044(19) _cell_measurement_reflns_used 3215 _cell_measurement_temperature 103.0(2) _cell_measurement_theta_max 27.1258 _cell_measurement_theta_min 2.5717 _cell_volume 1309.6(4) _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_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _diffrn_ambient_temperature 103.0(2) _diffrn_detector_area_resol_mean 8.3333 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.1342 _diffrn_reflns_av_unetI/netI 0.1290 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 14073 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.250 _diffrn_reflns_theta_min 3.033 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 0.296 _exptl_absorpt_correction_T_max 0.90 _exptl_absorpt_correction_T_min 0.53 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2014/4 (Bruker AXS Inc.)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.296 _exptl_crystal_description block _exptl_crystal_F_000 544 _exptl_crystal_size_max 0.420 _exptl_crystal_size_mid 0.400 _exptl_crystal_size_min 0.380 _refine_diff_density_max 0.515 _refine_diff_density_min -0.530 _refine_diff_density_rms 0.119 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 145 _refine_ls_number_reflns 2370 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.016 _refine_ls_R_factor_all 0.0943 _refine_ls_R_factor_gt 0.0751 _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^)+(0.1057P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1816 _refine_ls_wR_factor_ref 0.2027 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1779 _reflns_number_total 2370 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1nj01727f2.cif _cod_data_source_block 1957962 _cod_original_cell_volume 1309.5(4) _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 7060613 _shelx_shelxl_version_number 2018/3 _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_min 0.886 _shelx_estimated_absorpt_t_max 0.896 _shelx_res_file ; TITL xn_8_1 in P2(1)/n Cl.res created by SHELXL-2018/3 at 09:03:00 on 21-Apr-2021 CELL 0.71073 10.31170 12.18680 10.60440 90.0000 100.6861 90.0000 ZERR 4 0.00200 0.00230 0.00190 0.0000 0.0058 0.0000 LATT 1 SYMM 0.5-X, 0.5+Y, 0.5-Z SFAC C H B Cl N O UNIT 32 76 4 4 4 20 LIST 4 ! automatically inserted. Change 6 to 4 for CHECKCIF!! omit -1 0 1 omit 1 1 0 SHEL 99999 0.833 L.S. 8 ACTA BOND FMAP 2 PLAN 5 SIZE 0.38 0.40 0.42 TEMP -170 WGHT 0.105700 FVAR 0.20585 MOLE 1 B1 3 0.747022 0.131952 0.531283 11.00000 0.01636 0.01990 = 0.01673 0.00159 0.00294 0.00393 AFIX 3 H1B 2 0.718701 0.105740 0.627068 11.00000 -1.50000 H2B 2 0.768743 0.226790 0.534928 11.00000 -1.50000 AFIX 0 C1 1 0.427952 0.121656 0.286456 11.00000 0.02033 0.02577 = 0.02844 -0.00552 0.00240 0.00186 AFIX 23 H1A 2 0.398165 0.190996 0.241644 11.00000 -1.20000 H1C 2 0.350608 0.089080 0.315546 11.00000 -1.20000 AFIX 0 C2 1 0.528777 0.149744 0.403556 11.00000 0.01598 0.01596 = 0.02411 0.00047 0.00326 -0.00097 MOLE 2 C3 1 0.455625 0.602364 0.306113 11.00000 0.02645 0.02781 = 0.01462 -0.00627 0.00571 -0.00203 AFIX 23 H3A 2 0.486844 0.622481 0.397131 11.00000 -1.20000 H3B 2 0.374882 0.557289 0.300485 11.00000 -1.20000 AFIX 0 C4 1 0.597419 0.450121 0.341795 11.00000 0.03476 0.02866 = 0.01244 0.00451 0.00266 -0.00104 AFIX 23 H4A 2 0.520798 0.403439 0.349823 11.00000 -1.20000 H4B 2 0.638045 0.476536 0.428411 11.00000 -1.20000 AFIX 0 C5 1 0.695873 0.384987 0.285537 11.00000 0.02566 0.02285 = 0.01475 0.00442 -0.00275 0.00150 AFIX 23 H5A 2 0.768221 0.433266 0.269289 11.00000 -1.20000 H5B 2 0.734322 0.326601 0.345983 11.00000 -1.20000 AFIX 0 C6 1 0.718744 0.270096 0.112914 11.00000 0.02076 0.02202 = 0.03040 0.00434 0.00624 0.00843 AFIX 23 H6A 2 0.745214 0.205696 0.168662 11.00000 -1.20000 H6B 2 0.799180 0.312501 0.106600 11.00000 -1.20000 AFIX 0 C7 1 0.653324 0.232671 -0.017315 11.00000 0.03019 0.01519 = 0.02780 0.00089 0.00689 0.00435 AFIX 23 H7A 2 0.711067 0.180459 -0.052411 11.00000 -1.20000 H7B 2 0.569173 0.195204 -0.012586 11.00000 -1.20000 AFIX 0 C8 1 0.574384 0.296574 -0.227024 11.00000 0.02204 0.02302 = 0.01897 -0.01072 0.00269 0.00084 AFIX 23 H8A 2 0.492638 0.253539 -0.228788 11.00000 -1.20000 H8B 2 0.638075 0.250380 -0.262376 11.00000 -1.20000 AFIX 0 CL1 4 0.476772 0.030780 0.172652 11.00000 0.02750 0.02934 = 0.03041 -0.01185 -0.00042 0.00195 N1 5 0.871080 0.064530 0.507780 11.00000 0.01622 0.01568 = 0.01247 0.00081 0.00140 0.00254 AFIX 3 H3N 2 0.869451 -0.002225 0.523995 11.00000 -1.50000 H2N 2 0.937599 0.087495 0.560244 11.00000 -1.50000 H1N 2 0.876244 0.072093 0.428715 11.00000 -1.50000 AFIX 0 O1 6 0.644135 0.103127 0.415889 11.00000 0.01237 0.02040 = 0.02259 -0.00464 0.00098 0.00209 O2 6 0.495554 0.214889 0.478545 11.00000 0.02085 0.02978 = 0.03097 -0.00927 0.00578 0.00787 O3 6 0.555069 0.541303 0.259847 11.00000 0.02469 0.01960 = 0.01407 0.00114 0.00668 0.00263 O4 6 0.629523 0.337353 0.167737 11.00000 0.01652 0.01985 = 0.01873 -0.00003 -0.00062 0.00189 O5 6 0.629029 0.327324 -0.097995 11.00000 0.01894 0.01626 = 0.01848 -0.00193 0.00011 0.00020 HKLF 4 REM xn_8_1 in P2(1)/n REM wR2 = 0.2027, GooF = S = 1.016, Restrained GooF = 1.016 for all data REM R1 = 0.0751 for 1779 Fo > 4sig(Fo) and 0.0943 for all 2370 data REM 145 parameters refined using 0 restraints END WGHT 0.1058 0.0000 REM Highest difference peak 0.515, deepest hole -0.530, 1-sigma level 0.119 Q1 1 0.4853 0.5314 0.1785 11.00000 0.05 0.52 Q2 1 0.4077 0.0569 0.0810 11.00000 0.05 0.44 Q3 1 0.7051 0.3569 -0.0286 11.00000 0.05 0.42 Q4 1 0.7926 0.4541 0.5558 11.00000 0.05 0.40 Q5 1 0.7751 0.2464 0.1799 11.00000 0.05 0.39 ; _shelx_res_checksum 80687 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_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 B1 B 0.7470(4) 0.1320(3) 0.5313(3) 0.0177(8) Uani 1 1 d . . . . . H1B H 0.718701 0.105740 0.627068 0.027 Uiso 1 1 d R U . . . H2B H 0.768743 0.226790 0.534928 0.027 Uiso 1 1 d R U . . . C1 C 0.4280(3) 0.1217(3) 0.2865(3) 0.0251(8) Uani 1 1 d . . . . . H1A H 0.398165 0.190996 0.241644 0.030 Uiso 1 1 calc R U . . . H1C H 0.350608 0.089080 0.315546 0.030 Uiso 1 1 calc R U . . . C2 C 0.5288(3) 0.1497(2) 0.4036(3) 0.0187(7) Uani 1 1 d . . . . . C3 C 0.4556(4) 0.6024(3) 0.3061(3) 0.0227(8) Uani 1 1 d . . . . . H3A H 0.486844 0.622481 0.397131 0.027 Uiso 1 1 calc R U . . . H3B H 0.374882 0.557289 0.300485 0.027 Uiso 1 1 calc R U . . . C4 C 0.5974(4) 0.4501(3) 0.3418(3) 0.0255(8) Uani 1 1 d . . . . . H4A H 0.520798 0.403439 0.349823 0.031 Uiso 1 1 calc R U . . . H4B H 0.638045 0.476536 0.428411 0.031 Uiso 1 1 calc R U . . . C5 C 0.6959(3) 0.3850(3) 0.2855(3) 0.0219(8) Uani 1 1 d . . . . . H5A H 0.768221 0.433266 0.269289 0.026 Uiso 1 1 calc R U . . . H5B H 0.734322 0.326601 0.345983 0.026 Uiso 1 1 calc R U . . . C6 C 0.7187(4) 0.2701(3) 0.1129(3) 0.0242(8) Uani 1 1 d . . . . . H6A H 0.745214 0.205696 0.168662 0.029 Uiso 1 1 calc R U . . . H6B H 0.799180 0.312501 0.106600 0.029 Uiso 1 1 calc R U . . . C7 C 0.6533(4) 0.2327(2) -0.0173(3) 0.0242(8) Uani 1 1 d . . . . . H7A H 0.711067 0.180459 -0.052411 0.029 Uiso 1 1 calc R U . . . H7B H 0.569173 0.195204 -0.012586 0.029 Uiso 1 1 calc R U . . . C8 C 0.5744(3) 0.2966(3) -0.2270(3) 0.0215(8) Uani 1 1 d . . . . . H8A H 0.492638 0.253539 -0.228788 0.026 Uiso 1 1 calc R U . . . H8B H 0.638075 0.250380 -0.262376 0.026 Uiso 1 1 calc R U . . . Cl1 Cl 0.47677(9) 0.03078(7) 0.17265(8) 0.0298(3) Uani 1 1 d . . . . . N1 N 0.8711(3) 0.06453(19) 0.5078(2) 0.0150(6) Uani 1 1 d . . . . . H3N H 0.869451 -0.002225 0.523995 0.022 Uiso 1 1 d R U . . . H2N H 0.937599 0.087495 0.560244 0.022 Uiso 1 1 d R U . . . H1N H 0.876244 0.072093 0.428715 0.022 Uiso 1 1 d R U . . . O1 O 0.6441(2) 0.10313(16) 0.4159(2) 0.0187(5) Uani 1 1 d . . . . . O2 O 0.4956(2) 0.21489(18) 0.4785(2) 0.0271(6) Uani 1 1 d . . . . . O3 O 0.5551(2) 0.54130(16) 0.25985(19) 0.0191(6) Uani 1 1 d . . . . . O4 O 0.6295(2) 0.33735(17) 0.16774(19) 0.0189(5) Uani 1 1 d . . . . . O5 O 0.6290(2) 0.32732(16) -0.0980(2) 0.0183(5) Uani 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 B1 0.016(2) 0.0199(17) 0.0167(18) 0.0016(14) 0.0029(15) 0.0039(15) C1 0.020(2) 0.0258(18) 0.0284(18) -0.0055(14) 0.0024(16) 0.0019(14) C2 0.0160(17) 0.0160(15) 0.0241(17) 0.0005(13) 0.0033(15) -0.0010(13) C3 0.026(2) 0.0278(17) 0.0146(16) -0.0063(13) 0.0057(15) -0.0020(15) C4 0.035(2) 0.0287(18) 0.0124(16) 0.0045(13) 0.0027(15) -0.0010(15) C5 0.026(2) 0.0229(16) 0.0148(16) 0.0044(12) -0.0027(15) 0.0015(14) C6 0.0208(19) 0.0220(17) 0.0304(19) 0.0043(14) 0.0062(16) 0.0084(14) C7 0.030(2) 0.0152(16) 0.0278(18) 0.0009(13) 0.0069(16) 0.0043(14) C8 0.0220(19) 0.0230(16) 0.0190(17) -0.0107(13) 0.0027(15) 0.0008(14) Cl1 0.0275(6) 0.0293(5) 0.0304(6) -0.0118(3) -0.0004(4) 0.0020(4) N1 0.0162(15) 0.0157(13) 0.0125(13) 0.0008(10) 0.0014(11) 0.0025(11) O1 0.0124(13) 0.0204(11) 0.0226(12) -0.0046(9) 0.0010(10) 0.0021(9) O2 0.0208(14) 0.0298(13) 0.0310(13) -0.0093(10) 0.0058(11) 0.0079(11) O3 0.0247(14) 0.0196(11) 0.0141(11) 0.0011(8) 0.0067(10) 0.0026(9) O4 0.0165(13) 0.0199(11) 0.0187(11) 0.0000(8) -0.0006(10) 0.0019(9) O5 0.0189(13) 0.0163(11) 0.0185(11) -0.0019(8) 0.0001(10) 0.0002(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' B B 0.0013 0.0007 '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' 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 B1 N1 102.7(2) . . ? C2 C1 Cl1 117.6(2) . . ? O2 C2 O1 125.5(3) . . ? O2 C2 C1 116.9(3) . . ? O1 C2 C1 117.5(3) . . ? O3 C3 C8 109.0(3) . 3_665 ? O3 C4 C5 108.9(2) . . ? O4 C5 C4 108.2(3) . . ? O4 C6 C7 109.6(3) . . ? O5 C7 C6 107.8(2) . . ? O5 C8 C3 109.0(2) . 3_665 ? C2 O1 B1 118.2(2) . . ? C3 O3 C4 110.8(2) . . ? C5 O4 C6 110.3(2) . . ? C8 O5 C7 110.8(2) . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag B1 O1 1.505(4) . ? B1 N1 1.579(4) . ? C1 C2 1.504(5) . ? C1 Cl1 1.778(3) . ? C2 O2 1.217(4) . ? C2 O1 1.303(4) . ? C3 O3 1.426(4) . ? C3 C8 1.490(4) 3_665 ? C4 O3 1.428(4) . ? C4 C5 1.497(5) . ? C5 O4 1.431(4) . ? C6 O4 1.433(4) . ? C6 C7 1.492(5) . ? C7 O5 1.430(4) . ? C8 O5 1.430(4) . ?