#------------------------------------------------------------------------------ #$Date: 2024-07-05 21:00:14 +0300 (Fri, 05 Jul 2024) $ #$Revision: 293275 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/99/7159912.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_7159912 loop_ _publ_author_name 'Alexeev, Michael S.' 'Strelkova, Tatiana V.' 'Ilyin, Michael M.' 'Nelyubina, Yulia V.' 'Bespalov, Ivan A.' 'Medvedev, Michael G.' 'Khrustalev, Victor N.' 'Kuznetsov, Nikolai Yu' _publ_section_title ; Amine adducts of triallylborane as highly reactive allylborating agents for Cu(I)-catalyzed allylation of chiral sulfinylimines. ; _journal_issue 23 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 4680 _journal_page_last 4696 _journal_paper_doi 10.1039/d4ob00291a _journal_volume 22 _journal_year 2024 _chemical_absolute_configuration unk _chemical_formula_moiety 'C9 H18 B N' _chemical_formula_sum 'C9 H18 B N' _chemical_formula_weight 151.05 _space_group_crystal_system trigonal _space_group_IT_number 146 _space_group_name_Hall 'R 3' _space_group_name_H-M_alt 'R 3 :H' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary difmap _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2014/6 _audit_update_record ; 2023-08-21 deposited with the CCDC. 2024-04-17 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 120 _cell_formula_units_Z 3 _cell_length_a 10.5689(15) _cell_length_b 10.5689(15) _cell_length_c 8.3975(17) _cell_measurement_reflns_used 500 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 35.0 _cell_measurement_theta_min 5.0 _cell_volume 812.3(2) _computing_cell_refinement 'iMosflm (Battye et al., 2011)' _computing_data_collection 'Marccd (Doyle, 2011)' _computing_data_reduction iMosflm _computing_molecular_graphics 'SHELXTL (Sheldrick, 2015)' _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL (Sheldrick, 2015)' _computing_structure_solution 'SHELXT (Sheldrick, 2015)' _diffrn_ambient_temperature 100(2) _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.988 _diffrn_measurement_device_type 'Rayonix SX165 CCD' _diffrn_measurement_method '/f scan' _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.96990 _diffrn_reflns_av_R_equivalents 0.0785 _diffrn_reflns_av_unetI/netI 0.1776 _diffrn_reflns_Laue_measured_fraction_full 0.994 _diffrn_reflns_Laue_measured_fraction_max 0.988 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 2342 _diffrn_reflns_point_group_measured_fraction_full 0.994 _diffrn_reflns_point_group_measured_fraction_max 0.978 _diffrn_reflns_theta_full 35.587 _diffrn_reflns_theta_max 38.333 _diffrn_reflns_theta_min 5.265 _exptl_absorpt_coefficient_mu 0.102 _exptl_absorpt_correction_T_max 0.975 _exptl_absorpt_correction_T_min 0.966 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Scala (Evans, 2006)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 0.926 _exptl_crystal_description prism _exptl_crystal_F_000 252 _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _refine_diff_density_max 0.207 _refine_diff_density_min -0.286 _refine_diff_density_rms 0.034 _refine_ls_abs_structure_details ; Flack x determined using 133 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -2.3(10) _refine_ls_extinction_coef 0.046(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 0.871 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 36 _refine_ls_number_reflns 749 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 0.871 _refine_ls_R_factor_all 0.1009 _refine_ls_R_factor_gt 0.0721 _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^)] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1610 _refine_ls_wR_factor_ref 0.1861 _reflns_Friedel_coverage 0.980 _reflns_Friedel_fraction_full 0.994 _reflns_Friedel_fraction_max 0.967 _reflns_number_gt 427 _reflns_number_total 749 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4ob00291a3.cif _cod_data_source_block 2887 _cod_depositor_comments 'Adding full bibliography for 7159912--7159916.cif.' _cod_original_cell_volume 812.3(3) _cod_original_sg_symbol_H-M 'R 3' _cod_database_code 7159912 _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 0.973 _shelx_estimated_absorpt_t_max 0.983 _shelxl_version_number 2014/6 _shelx_res_file ; TITL 2887 in R3 CELL 0.96990 10.5689 10.5689 8.3975 90.000 90.000 120.000 ZERR 3.00 0.0015 0.0015 0.0017 0.000 0.000 0.000 LATT -3 SYMM -Y, +X-Y, +Z SYMM +Y-X, -X, +Z SFAC C H B N DISP B 0.004 0.001 12.899 DISP C 0.007 0.003 25.571 DISP H -0 0 0.636 DISP N 0.013 0.007 47.42 UNIT 27 54 3 3 TEMP -173.0 SIZE 0.15 0.20 0.25 OMIT 3 9 0 OMIT -8 6 4 OMIT -1 2 6 OMIT -8 6 1 OMIT 0 2 7 OMIT -7 6 5 OMIT -7 5 6 OMIT 1 6 4 OMIT -2 8 5 OMIT -4 5 6 OMIT 4 8 2 OMIT -3 2 7 OMIT 0 0 6 OMIT -4 9 5 OMIT -5 9 4 OMIT 0 9 3 OMIT -9 6 3 OMIT 1 1 6 L.S. 12 BOND $H ACTA CONF TWIN 0 1 0 1 0 0 0 0 -1 2 WGHT 0.000000 EXTI 0.046069 BASF 0.47612 FVAR 1.81826 N1 4 0.666667 0.333333 0.625925 10.33333 0.04957 0.04957 = 0.07857 0.00000 0.00000 0.02479 AFIX 3 H1 2 0.608750 0.368200 0.662045 11.00000 -1.50000 AFIX 0 B1 3 0.666667 0.333333 0.430644 10.33333 0.06838 0.06838 = 0.06661 0.00000 0.00000 0.03419 C1 1 0.701109 0.496380 0.377473 11.00000 0.06995 0.06765 = 0.08585 0.00544 -0.00001 0.03324 AFIX 23 H1A 2 0.707563 0.503134 0.259874 11.00000 -1.20000 H1B 2 0.618038 0.508860 0.410316 11.00000 -1.20000 AFIX 0 C2 1 0.840648 0.620802 0.447068 11.00000 0.06136 0.06386 = 0.10224 0.04164 0.02350 0.03472 AFIX 43 H2 2 0.930116 0.632504 0.407566 11.00000 -1.20000 AFIX 0 C3 1 0.849766 0.713391 0.555991 11.00000 0.06739 0.05356 = 0.10033 0.01793 0.00937 0.02977 AFIX 93 H3A 2 0.763380 0.706253 0.599275 11.00000 -1.20000 H3B 2 0.942778 0.787810 0.591856 11.00000 -1.20000 AFIX 0 HKLF 4 REM 2887 in R3 REM R1 = 0.0721 for 427 Fo > 4sig(Fo) and 0.1009 for all 749 data REM 36 parameters refined using 1 restraints END WGHT 0.0000 0.0000 REM Highest difference peak 0.207, deepest hole -0.286, 1-sigma level 0.034 Q1 1 0.6520 0.3841 0.7163 11.00000 0.05 0.11 Q2 1 0.6259 0.5333 0.6122 11.00000 0.05 0.10 Q3 1 0.8567 0.7364 0.3649 11.00000 0.05 0.10 Q4 1 0.5089 0.5331 0.4762 11.00000 0.05 0.10 Q5 1 0.8080 0.5790 0.6220 11.00000 0.05 0.10 Q6 1 0.6974 0.4804 0.5823 11.00000 0.05 0.09 Q7 1 0.9138 0.6824 0.3077 11.00000 0.05 0.09 Q8 1 0.8571 0.6550 0.2690 11.00000 0.05 0.09 Q9 1 1.1034 0.7754 0.4835 11.00000 0.05 0.09 Q10 1 0.8034 0.6269 0.3875 11.00000 0.05 0.08 Q11 1 0.9092 0.6481 0.6401 11.00000 0.05 0.08 Q12 1 0.8521 0.5808 0.3855 11.00000 0.05 0.08 Q13 1 0.5709 0.4588 0.4578 11.00000 0.05 0.08 Q14 1 0.9394 0.5935 0.3538 11.00000 0.05 0.08 Q15 1 0.6817 0.6457 0.7367 11.00000 0.05 0.08 Q16 1 0.4691 0.4669 0.3937 11.00000 0.05 0.07 Q17 1 0.8019 0.5708 0.4905 11.00000 0.05 0.07 Q18 1 0.5290 0.4793 0.1914 11.00000 0.05 0.07 Q19 1 0.7059 0.5770 0.5012 11.00000 0.05 0.07 Q20 1 0.7314 0.3845 0.3532 11.00000 0.05 0.07 ; _shelx_res_checksum 84785 loop_ _space_group_symop_operation_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' 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 N1 N 0.6667 0.3333 0.6259(9) 0.059(2) Uani 1 3 d S T P . . H1 H 0.6088 0.3682 0.6620 0.089 Uiso 1 1 d R U . . . B1 B 0.6667 0.3333 0.4306(14) 0.068(3) Uani 1 3 d S T P . . C1 C 0.7011(8) 0.4964(7) 0.3775(11) 0.075(2) Uani 1 1 d . . . . . H1A H 0.7076 0.5031 0.2599 0.090 Uiso 1 1 calc R U . . . H1B H 0.6180 0.5089 0.4103 0.090 Uiso 1 1 calc R U . . . C2 C 0.8406(6) 0.6208(7) 0.4471(7) 0.074(2) Uani 1 1 d . . . . . H2 H 0.9301 0.6325 0.4076 0.089 Uiso 1 1 calc R U . . . C3 C 0.8498(8) 0.7134(6) 0.5560(7) 0.0740(18) Uani 1 1 d . . . . . H3A H 0.7634 0.7063 0.5993 0.089 Uiso 1 1 calc R U . . . H3B H 0.9428 0.7878 0.5919 0.089 Uiso 1 1 calc R U . . . 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 N1 0.050(3) 0.050(3) 0.079(6) 0.000 0.000 0.0248(13) B1 0.068(5) 0.068(5) 0.067(7) 0.000 0.000 0.034(2) C1 0.070(4) 0.068(4) 0.086(4) 0.005(4) 0.000(3) 0.033(4) C2 0.061(4) 0.064(4) 0.102(5) 0.042(4) 0.023(4) 0.035(3) C3 0.067(4) 0.054(4) 0.100(5) 0.018(4) 0.009(4) 0.030(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0070 0.0030 '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 0.0040 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0130 0.0070 '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 B1 N1 H1 109.5 . . ? C1 B1 C1 112.8(4) 2_655 . ? C1 B1 N1 105.8(5) . . ? C2 C1 B1 114.6(5) . . ? C2 C1 H1A 108.6 . . ? B1 C1 H1A 108.6 . . ? C2 C1 H1B 108.6 . . ? B1 C1 H1B 108.6 . . ? H1A C1 H1B 107.6 . . ? C3 C2 C1 126.4(6) . . ? C3 C2 H2 116.8 . . ? C1 C2 H2 116.8 . . ? C2 C3 H3A 120.0 . . ? C2 C3 H3B 120.0 . . ? H3A C3 H3B 120.0 . . ? 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 N1 B1 1.640(14) . ? N1 H1 0.9100 . ? B1 C1 1.635(7) . ? C1 C2 1.519(9) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.307(9) . ? C2 H2 0.9500 . ? C3 H3A 0.9500 . ? C3 H3B 0.9500 . ? 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 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 B1 C1 C2 -60.0(12) 3_665 . . . ? C1 B1 C1 C2 170.6(6) 2_655 . . . ? N1 B1 C1 C2 55.3(6) . . . . ? B1 C1 C2 C3 -109.6(8) . . . . ?