#------------------------------------------------------------------------------ #$Date: 2017-06-27 04:13:01 +0300 (Tue, 27 Jun 2017) $ #$Revision: 198148 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/54/63/1546386.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_1546386 loop_ _publ_author_name 'Landmann, Johannes' 'Hennig, Philipp T.' 'Ignat'ev, Nikolai' 'Finze, Maik' _publ_section_title ; Borylation of Fluorinated Arenes with the Boron-centred Nucleophile B(CN)32− -- a Unique Entry to Aryltricyanoborates ; _journal_name_full 'Chem. Sci.' _journal_paper_doi 10.1039/C7SC02249B _journal_year 2017 _chemical_formula_moiety 'C12 H2 B2 F2 N6, 2(C6 H16 N)' _chemical_formula_sum 'C24 H34 B2 F2 N8' _chemical_formula_weight 494.21 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary iterative _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2017-05-09 deposited with the CCDC. 2017-06-26 downloaded from the CCDC. ; _cell_angle_alpha 98.148(9) _cell_angle_beta 105.678(9) _cell_angle_gamma 106.755(8) _cell_formula_units_Z 1 _cell_length_a 7.2310(18) _cell_length_b 10.113(3) _cell_length_c 10.502(3) _cell_measurement_reflns_used 2372 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 26.74 _cell_measurement_theta_min 2.62 _cell_volume 687.6(3) _computing_cell_refinement 'Saint+ ver. V8.34A (Bruker AXS)' _computing_data_collection 'APEX2 ver. 2014.9 (Bruker AXS)' _computing_data_reduction 'Saint+ ver. V8.34A (Bruker AXS)' _computing_molecular_graphics 'ShelXLe (Huebschle et all, 2011)' _computing_publication_material 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXT (Sheldrick, 2014)' _diffrn_ambient_temperature 100(2) _diffrn_detector 'CCD area detector (Apex2)' _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.977 _diffrn_measurement_device_type 'Bruker X8-APEX II' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0646 _diffrn_reflns_av_unetI/netI 0.0725 _diffrn_reflns_Laue_measured_fraction_full 0.991 _diffrn_reflns_Laue_measured_fraction_max 0.977 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 9798 _diffrn_reflns_point_group_measured_fraction_full 0.991 _diffrn_reflns_point_group_measured_fraction_max 0.977 _diffrn_reflns_theta_full 26.000 _diffrn_reflns_theta_max 26.973 _diffrn_reflns_theta_min 2.166 _diffrn_source 'rotating-anode (Nonius FR-591)' _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_T_max 0.7454 _exptl_absorpt_correction_T_min 0.5933 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SadAbs 2014/5 (Bruker AXS)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.194 _exptl_crystal_description block _exptl_crystal_F_000 262 _exptl_crystal_size_max 0.340 _exptl_crystal_size_mid 0.180 _exptl_crystal_size_min 0.160 _refine_diff_density_max 0.325 _refine_diff_density_min -0.328 _refine_diff_density_rms 0.064 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.984 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 231 _refine_ls_number_reflns 2926 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.984 _refine_ls_R_factor_all 0.0770 _refine_ls_R_factor_gt 0.0458 _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^)+(0.0668P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1081 _refine_ls_wR_factor_ref 0.1260 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1980 _reflns_number_total 2926 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c7sc02249b2.cif _cod_data_source_block JL086_JL_Et3NH2B4D _cod_database_code 1546386 _shelx_shelxl_version_number 2014/7 _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 0.972 _shelx_estimated_absorpt_t_max 0.987 _shelx_res_file ; fertig_a.res created by SHELXL-2014/7 TITL fertig_a.res in P-1 REM Old TITL fertig in P-1 REM SHELXT solution in P-1 REM R1 0.148, Rweak 0.007, Alpha 0.033, Orientation as input REM Formula found by SHELXT: C12 B N4 F CELL 0.71073 7.2310 10.1125 10.5015 98.148 105.678 106.755 ZERR 1.000 0.0018 0.0026 0.0028 0.009 0.009 0.008 LATT 1 SFAC C H B N F UNIT 24 34 2 8 2 TEMP -173 SIZE 0.16 0.18 0.34 L.S. 10 BOND $H ACTA 52 LIST 4 FMAP 2 PLAN 20 WGHT 0.066800 FVAR 1.40706 F1 5 -0.180371 0.217324 0.893551 11.00000 0.03340 0.00791 = 0.04003 -0.00816 0.02313 -0.00432 H1 2 -0.290927 0.370694 1.042470 11.00000 0.01893 N1 4 0.277766 0.131401 0.919804 11.00000 0.03342 0.02514 = 0.02622 0.00863 0.01093 0.01300 C1 1 0.234869 0.220306 0.876885 11.00000 0.01631 0.01643 = 0.01306 -0.00047 0.00569 0.00333 B1 3 0.166097 0.341476 0.815703 11.00000 0.01620 0.01151 = 0.01273 -0.00030 0.00455 0.00311 C2 1 -0.008468 0.265806 0.671243 11.00000 0.01900 0.01367 = 0.01758 0.00255 0.00945 0.00532 N2 4 -0.133694 0.212149 0.567699 11.00000 0.02340 0.02374 = 0.01818 0.00012 0.00428 0.00671 N3 4 0.483381 0.527023 0.764462 11.00000 0.02557 0.01604 = 0.02458 0.00300 0.01333 0.00583 C3 1 0.354463 0.447653 0.787058 11.00000 0.02153 0.01312 = 0.01408 -0.00022 0.00595 0.00771 C4 1 0.083135 0.427904 0.915214 11.00000 0.01452 0.01223 = 0.01097 0.00080 0.00299 0.00358 C5 1 -0.087034 0.360874 0.946836 11.00000 0.01669 0.00640 = 0.01790 -0.00227 0.00529 -0.00170 C6 1 -0.172700 0.426155 1.027317 11.00000 0.01420 0.01491 = 0.01663 0.00075 0.00722 0.00008 C11 1 0.930080 0.771061 0.701505 11.00000 0.01589 0.01962 = 0.02124 0.00246 0.00559 0.00332 H11 2 0.779175 0.982228 0.724890 11.00000 0.01986 N11 4 0.716573 0.769639 0.687107 11.00000 0.01681 0.01105 = 0.01477 0.00112 0.00485 0.00172 C12 1 0.933116 0.625118 0.647222 11.00000 0.02293 0.02239 = 0.02691 0.00564 0.00863 0.00781 H12 2 0.807685 0.919381 0.857387 11.00000 0.02959 C13 1 0.575871 0.727942 0.541061 11.00000 0.02048 0.01517 = 0.01459 -0.00206 0.00195 0.00579 H13 2 0.443428 0.817774 0.799426 11.00000 0.02306 C14 1 0.631376 0.835570 0.459531 11.00000 0.03140 0.02705 = 0.01802 0.00674 0.00980 0.01362 H14 2 0.522780 0.983668 0.832072 11.00000 0.03373 C15 1 0.719467 0.907420 0.766904 11.00000 0.02293 0.01206 = 0.01747 -0.00270 0.00724 0.00007 H15 2 0.418365 0.898155 0.682136 11.00000 0.03102 C16 1 0.509894 0.901157 0.769595 11.00000 0.02376 0.01726 = 0.01906 -0.00116 0.00742 0.00423 H17 2 0.991675 0.841111 0.652743 11.00000 0.01551 H18 2 0.863793 0.559159 0.694960 11.00000 0.02430 H19 2 1.080344 0.634478 0.670079 11.00000 0.03439 H20 2 0.866954 0.593499 0.550508 11.00000 0.02643 H21 2 0.577753 0.635397 0.499367 11.00000 0.03040 H22 2 0.434855 0.715537 0.545577 11.00000 0.01661 H24 2 0.621133 0.928098 0.498613 11.00000 0.03372 H25 2 0.535949 0.800234 0.369823 11.00000 0.03702 H26 2 0.774684 0.852607 0.454563 11.00000 0.03928 H31 2 0.658207 0.697424 0.727135 11.00000 0.02339 H16 2 1.003511 0.805039 0.799014 11.00000 0.03091 HKLF 4 REM fertig_a.res in P-1 REM R1 = 0.0458 for 1980 Fo > 4sig(Fo) and 0.0770 for all 2926 data REM 231 parameters refined using 0 restraints END WGHT 0.0668 0.0000 REM Highest difference peak 0.325, deepest hole -0.328, 1-sigma level 0.064 Q1 1 0.2681 0.3957 0.8124 11.00000 0.05 0.33 Q2 1 0.0243 0.3851 0.9652 11.00000 0.05 0.27 Q3 1 0.3271 0.0913 0.9999 11.00000 0.05 0.27 Q4 1 -0.0558 0.4083 0.8837 11.00000 0.05 0.25 Q5 1 0.2947 0.4838 0.7547 11.00000 0.05 0.24 Q6 1 0.5905 0.7871 0.4956 11.00000 0.05 0.24 Q7 1 0.1325 0.3893 0.8647 11.00000 0.05 0.23 Q8 1 0.4202 0.4803 0.8145 11.00000 0.05 0.23 Q9 1 0.4705 0.5855 0.7155 11.00000 0.05 0.22 Q10 1 0.7361 0.6965 0.7407 11.00000 0.05 0.22 Q11 1 0.1651 0.2697 0.8378 11.00000 0.05 0.22 Q12 1 0.2080 0.0754 0.9854 11.00000 0.05 0.21 Q13 1 0.2557 0.2834 0.8371 11.00000 0.05 0.21 Q14 1 1.0261 1.0447 0.7533 11.00000 0.05 0.21 Q15 1 -0.0514 0.2986 0.6045 11.00000 0.05 0.20 Q16 1 0.0468 0.3016 0.6222 11.00000 0.05 0.20 Q17 1 0.8209 0.6364 0.7864 11.00000 0.05 0.20 Q18 1 0.3592 0.1954 0.9030 11.00000 0.05 0.20 Q19 1 0.9066 0.8293 0.6292 11.00000 0.05 0.20 Q20 1 -0.1421 0.2628 0.8182 11.00000 0.05 0.19 ; _shelx_res_checksum 11008 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' 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 F1 F -0.18037(16) 0.21732(10) 0.89355(11) 0.0289(3) Uani 1 1 d H1 H -0.291(3) 0.371(2) 1.0425(18) 0.019(5) Uiso 1 1 d N1 N 0.2778(2) 0.13140(17) 0.91980(16) 0.0271(4) Uani 1 1 d C1 C 0.2349(3) 0.22031(18) 0.87689(16) 0.0160(4) Uani 1 1 d B1 B 0.1661(3) 0.34148(19) 0.81570(17) 0.0142(4) Uani 1 1 d C2 C -0.0085(3) 0.26581(17) 0.67124(16) 0.0162(4) Uani 1 1 d N2 N -0.1337(2) 0.21215(16) 0.56770(14) 0.0232(4) Uani 1 1 d N3 N 0.4834(2) 0.52702(15) 0.76446(15) 0.0215(4) Uani 1 1 d C3 C 0.3545(3) 0.44765(17) 0.78706(16) 0.0162(4) Uani 1 1 d C4 C 0.0831(2) 0.42790(16) 0.91521(15) 0.0133(4) Uani 1 1 d C5 C -0.0870(3) 0.36087(16) 0.94684(16) 0.0156(4) Uani 1 1 d C6 C -0.1727(3) 0.42615(18) 1.02732(16) 0.0162(4) Uani 1 1 d C11 C 0.9301(3) 0.77106(19) 0.70150(18) 0.0199(4) Uani 1 1 d H11 H 0.779(3) 0.982(2) 0.7249(19) 0.020(5) Uiso 1 1 d N11 N 0.7166(2) 0.76964(15) 0.68711(13) 0.0152(3) Uani 1 1 d C12 C 0.9331(3) 0.6251(2) 0.6472(2) 0.0240(4) Uani 1 1 d H12 H 0.808(3) 0.919(2) 0.857(2) 0.030(5) Uiso 1 1 d C13 C 0.5759(3) 0.72794(18) 0.54106(16) 0.0182(4) Uani 1 1 d H13 H 0.443(3) 0.818(2) 0.7994(19) 0.023(5) Uiso 1 1 d C14 C 0.6314(3) 0.8356(2) 0.45953(18) 0.0242(4) Uani 1 1 d H14 H 0.523(3) 0.984(2) 0.832(2) 0.034(6) Uiso 1 1 d C15 C 0.7195(3) 0.90742(18) 0.76690(18) 0.0194(4) Uani 1 1 d H15 H 0.418(3) 0.898(2) 0.682(2) 0.031(5) Uiso 1 1 d C16 C 0.5099(3) 0.9012(2) 0.76960(18) 0.0212(4) Uani 1 1 d H17 H 0.992(3) 0.8411(19) 0.6527(18) 0.016(4) Uiso 1 1 d H18 H 0.864(3) 0.559(2) 0.695(2) 0.024(5) Uiso 1 1 d H19 H 1.080(3) 0.634(2) 0.670(2) 0.034(6) Uiso 1 1 d H20 H 0.867(3) 0.593(2) 0.551(2) 0.026(5) Uiso 1 1 d H21 H 0.578(3) 0.635(2) 0.499(2) 0.030(5) Uiso 1 1 d H22 H 0.435(3) 0.7155(19) 0.5456(18) 0.017(5) Uiso 1 1 d H24 H 0.621(3) 0.928(2) 0.499(2) 0.034(6) Uiso 1 1 d H25 H 0.536(3) 0.800(2) 0.370(2) 0.037(6) Uiso 1 1 d H26 H 0.775(4) 0.853(2) 0.455(2) 0.039(6) Uiso 1 1 d H31 H 0.658(3) 0.697(2) 0.7271(19) 0.023(5) Uiso 1 1 d H16 H 1.004(3) 0.805(2) 0.799(2) 0.031(5) Uiso 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 F1 0.0334(7) 0.0079(5) 0.0400(6) -0.0082(4) 0.0231(5) -0.0043(4) N1 0.0334(10) 0.0251(9) 0.0262(8) 0.0086(7) 0.0109(7) 0.0130(7) C1 0.0163(9) 0.0164(9) 0.0131(8) -0.0005(6) 0.0057(6) 0.0033(7) B1 0.0162(10) 0.0115(9) 0.0127(8) -0.0003(7) 0.0045(7) 0.0031(7) C2 0.0190(9) 0.0137(8) 0.0176(8) 0.0025(6) 0.0095(7) 0.0053(7) N2 0.0234(9) 0.0237(8) 0.0182(8) 0.0001(6) 0.0043(6) 0.0067(7) N3 0.0256(9) 0.0160(8) 0.0246(8) 0.0030(6) 0.0133(7) 0.0058(7) C3 0.0215(10) 0.0131(8) 0.0141(8) -0.0002(6) 0.0059(7) 0.0077(7) C4 0.0145(9) 0.0122(8) 0.0110(7) 0.0008(6) 0.0030(6) 0.0036(7) C5 0.0167(9) 0.0064(7) 0.0179(8) -0.0023(6) 0.0053(7) -0.0017(6) C6 0.0142(9) 0.0149(8) 0.0166(8) 0.0008(6) 0.0072(7) 0.0001(7) C11 0.0159(10) 0.0196(9) 0.0212(9) 0.0025(7) 0.0056(7) 0.0033(7) N11 0.0168(8) 0.0110(7) 0.0148(7) 0.0011(5) 0.0048(6) 0.0017(6) C12 0.0229(11) 0.0224(10) 0.0269(10) 0.0056(8) 0.0086(8) 0.0078(8) C13 0.0205(11) 0.0152(9) 0.0146(8) -0.0021(6) 0.0019(7) 0.0058(7) C14 0.0314(12) 0.0271(11) 0.0180(9) 0.0067(8) 0.0098(8) 0.0136(9) C15 0.0229(10) 0.0121(9) 0.0175(9) -0.0027(6) 0.0072(7) 0.0001(7) C16 0.0238(10) 0.0173(9) 0.0191(9) -0.0012(7) 0.0074(7) 0.0042(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' F F 0.0171 0.0103 '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 N1 C1 B1 177.88(18) . . C2 B1 C1 107.54(13) . . C2 B1 C3 106.76(13) . . C1 B1 C3 109.36(14) . . C2 B1 C4 110.41(14) . . C1 B1 C4 112.06(13) . . C3 B1 C4 110.52(14) . . N2 C2 B1 179.69(18) . . N3 C3 B1 176.83(17) . . C5 C4 C6 115.18(15) . 2_567 C5 C4 B1 121.17(14) . . C6 C4 B1 123.63(15) 2_567 . F1 C5 C4 117.56(15) . . F1 C5 C6 117.04(15) . . C4 C5 C6 125.40(16) . . C5 C6 C4 119.42(17) . 2_567 C5 C6 H1 119.0(12) . . C4 C6 H1 121.6(11) 2_567 . N11 C11 C12 111.98(15) . . N11 C11 H17 108.7(10) . . C12 C11 H17 110.7(11) . . N11 C11 H16 104.4(12) . . C12 C11 H16 111.4(12) . . H17 C11 H16 109.4(15) . . C11 N11 C15 111.19(13) . . C11 N11 C13 113.90(14) . . C15 N11 C13 112.90(13) . . C11 N11 H31 107.0(12) . . C15 N11 H31 106.4(12) . . C13 N11 H31 104.8(11) . . C11 C12 H18 107.4(12) . . C11 C12 H19 106.1(13) . . H18 C12 H19 110.9(17) . . C11 C12 H20 111.5(12) . . H18 C12 H20 110.9(16) . . H19 C12 H20 109.8(17) . . C14 C13 N11 114.04(15) . . C14 C13 H21 111.0(12) . . N11 C13 H21 107.0(12) . . C14 C13 H22 109.9(10) . . N11 C13 H22 106.1(10) . . H21 C13 H22 108.6(15) . . C13 C14 H24 111.0(12) . . C13 C14 H25 108.0(13) . . H24 C14 H25 107.7(17) . . C13 C14 H26 112.1(11) . . H24 C14 H26 109.1(17) . . H25 C14 H26 108.8(18) . . C16 C15 N11 112.12(14) . . C16 C15 H11 112.6(11) . . N11 C15 H11 106.3(12) . . C16 C15 H12 109.9(12) . . N11 C15 H12 104.8(12) . . H11 C15 H12 110.9(16) . . C15 C16 H13 111.9(11) . . C15 C16 H14 108.8(12) . . H13 C16 H14 107.9(16) . . C15 C16 H15 113.2(12) . . H13 C16 H15 107.2(16) . . H14 C16 H15 107.6(17) . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 F1 C5 1.3699(19) . N1 C1 1.144(2) . C1 B1 1.601(3) . B1 C2 1.600(2) . B1 C3 1.603(3) . B1 C4 1.612(2) . C2 N2 1.146(2) . N3 C3 1.145(2) . C4 C5 1.374(2) . C4 C6 1.395(2) 2_567 C5 C6 1.376(2) . C6 C4 1.395(2) 2_567 C6 H1 0.95(2) . C11 N11 1.506(2) . C11 C12 1.513(3) . C11 H17 1.003(18) . C11 H16 0.97(2) . N11 C15 1.512(2) . N11 C13 1.514(2) . N11 H31 0.95(2) . C12 H18 0.993(19) . C12 H19 1.00(2) . C12 H20 0.96(2) . C13 C14 1.509(3) . C13 H21 0.98(2) . C13 H22 1.006(19) . C14 H24 1.00(2) . C14 H25 0.95(2) . C14 H26 1.02(2) . C15 C16 1.507(3) . C15 H11 0.981(19) . C15 H12 0.96(2) . C16 H13 0.98(2) . C16 H14 0.95(2) . C16 H15 0.97(2) .