# Supplementary Material (ESI) for PCCP # This journal is (c) the Owner Societies 2010 data_global _journal_name_full Phys.Chem.Chem.Phys.(PCCP) _journal_coden_cambridge 1326 _publ_section_title ;On the Nature of the B-N Interaction and the Conformational Flexibility of Arylboronic Azaesters ; _publ_contact_author_name 'Krysztof Wozniak' _publ_contact_author_email kwozniak@chem.uw.edu.pl loop_ _publ_author_name 'Krysztof Wozniak' 'Krzysztof Durka' 'Radoslaw Kaminski' 'Sergiusz Lulinski' 'Janusz Serwatowski' # Attachment '- 1_iam.cif' data_1_iam _database_code_depnum_ccdc_archive 'CCDC 771324' #TrackingRef '- 1_iam.cif' _chemical_name_systematic ; 6-tert-butyl-2-(3',5'-difluorophenyl)-(N-B)-1,3,6,2-dioxazaborocan ; _chemical_name_common '3,5-diflurophenyl tert-butyl boronic azaester' _chemical_melting_point 'not measured' _chemical_formula_moiety 'C14 H20 B1 F2 N1 O2 ' _chemical_formula_sum 'C14 H20 B1 F2 N1 O2' _chemical_formula_weight 283.12 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' _space_group_IT_number 14 loop_ _symmetry_equiv_pos_as_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' _cell_length_a 6.6681(2) _cell_length_b 21.4324(6) _cell_length_c 9.8980(3) _cell_angle_alpha 90.00 _cell_angle_beta 102.551(2) _cell_angle_gamma 90.00 _cell_volume 1380.75(7) _cell_formula_units_Z 4 _cell_measurement_temperature 90(2) _cell_measurement_reflns_used 9441 _cell_measurement_theta_min 3.5468 _cell_measurement_theta_max 52.1998 _exptl_crystal_description unspecified _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.362 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 600 _exptl_absorpt_coefficient_mu 0.107 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.932 _exptl_absorpt_correction_T_max 1.006 _exptl_absorpt_process_details ; R. H. Blessing, Acta Cryst., 1995, A51, 33-38 ; _diffrn_source 'rotating-anode X-ray source' _diffrn_radiation_source 'TXS rotating anode' _diffrn_ambient_temperature 90(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator 'multi-layer optics' _diffrn_radiation_probe X-ray _diffrn_detector 'APEXII CCD camera' _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Bruker APEXII' _diffrn_measurement_method 'omega scans' _diffrn_orient_matrix_type 'X-axis to radiation source' _diffrn_orient_matrix_UB_11 0.530864E-1 _diffrn_orient_matrix_UB_12 0.433861E-1 _diffrn_orient_matrix_UB_13 -0.499095E-2 _diffrn_orient_matrix_UB_21 -0.933281E-1 _diffrn_orient_matrix_UB_22 0.55535E-2 _diffrn_orient_matrix_UB_23 -0.930111E-1 _diffrn_orient_matrix_UB_31 -0.109894 _diffrn_orient_matrix_UB_32 0.162421E-1 _diffrn_orient_matrix_UB_33 0.451343E-1 _diffrn_reflns_av_sigmaI/netI 0.0348 _diffrn_reflns_number 123017 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 47 _diffrn_reflns_limit_k_min -47 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_theta_max 52.324 _diffrn_reflns_theta_min 2.312 _diffrn_reflns_av_r_equivalents 0.0440 _reflns_number_total 15927 _reflns_number_gt 12353 _reflns_threshold_expression >2sigma(I) _diffrn_reflns_reduction_process ; Scaled and merged with SORTAV R. H. Blessing, Cryst. Rev., 1987, 1, 3-58 R. H. Blessing, J. Appl. Cryst., 1989, 22, 396-397 ; _computing_data_collection 'Bruker APEX2 software' _computing_cell_refinement 'Bruker APEX2 software' _computing_data_reduction ; SAINT intergration software, Bruker AXS SORTAV, R. H. Blessing, Acta Cryst., 1995, A51, 33-38 ; _computing_structure_solution ; SHELXS-97, G. M. Sheldrick, Acta. Cryst., 2008, A64, 112-122 ; _computing_structure_refinement ; SHELXS-97, G. M. Sheldrick, Acta. Cryst., 2008, A64, 112-122 ; _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0731P)^2^+0.0344P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 15927 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0564 _refine_ls_R_factor_gt 0.0384 _refine_ls_wR_factor_ref 0.1304 _refine_ls_wR_factor_gt 0.1138 _refine_ls_goodness_of_fit_ref 1.110 _refine_ls_restrained_S_all 1.110 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.33089(4) 0.173859(12) -0.08769(3) 0.01041(3) Uani 1 1 d . . . O1 O 0.67913(4) 0.211786(14) 0.01665(3) 0.01561(4) Uani 1 1 d . . . O2 O 0.38733(5) 0.237947(14) 0.12309(3) 0.01622(4) Uani 1 1 d . . . C1 C 0.58181(4) 0.138599(14) 0.18699(3) 0.01083(4) Uani 1 1 d . . . C2 C 0.77755(5) 0.111861(16) 0.20273(3) 0.01320(4) Uani 1 1 d . . . H2 H 0.8594 0.1207 0.1376 0.016 Uiso 1 1 calc R . . C11 C 0.28438(5) 0.106509(16) -0.13840(3) 0.01347(4) Uani 1 1 d . . . C6 C 0.46768(5) 0.124619(15) 0.28657(3) 0.01258(4) Uani 1 1 d . . . H6 H 0.3348 0.1421 0.2793 0.015 Uiso 1 1 calc R . . F1 F 1.04040(4) 0.047059(17) 0.32505(4) 0.02412(6) Uani 1 1 d . . . F2 F 0.44091(5) 0.073887(16) 0.49330(3) 0.02203(5) Uani 1 1 d . . . C5 C 0.54972(5) 0.085271(16) 0.39556(3) 0.01392(4) Uani 1 1 d . . . C4 C 0.74182(6) 0.057830(17) 0.41256(4) 0.01533(5) Uani 1 1 d . . . H4 H 0.7949 0.0307 0.4876 0.018 Uiso 1 1 calc R . . C10 C 0.14112(5) 0.207270(18) -0.06989(4) 0.01481(5) Uani 1 1 d . . . H10A H 0.0540 0.1797 -0.0266 0.018 Uiso 1 1 calc R . . H10B H 0.0600 0.2220 -0.1602 0.018 Uiso 1 1 calc R . . C9 C 0.22004(6) 0.261887(18) 0.02376(4) 0.01666(5) Uani 1 1 d . . . H9A H 0.2655 0.2962 -0.0295 0.020 Uiso 1 1 calc R . . H9B H 0.1117 0.2779 0.0690 0.020 Uiso 1 1 calc R . . C8 C 0.42672(5) 0.210024(18) -0.18860(3) 0.01460(5) Uani 1 1 d . . . H8A H 0.3243 0.2385 -0.2445 0.018 Uiso 1 1 calc R . . H8B H 0.4765 0.1811 -0.2520 0.018 Uiso 1 1 calc R . . C3 C 0.85111(5) 0.072578(17) 0.31313(4) 0.01487(5) Uani 1 1 d . . . C7 C 0.60602(6) 0.247430(18) -0.10399(4) 0.01653(5) Uani 1 1 d . . . H7A H 0.7152 0.2531 -0.1566 0.020 Uiso 1 1 calc R . . H7B H 0.5591 0.2890 -0.0800 0.020 Uiso 1 1 calc R . . C13 C 0.48595(7) 0.07243(2) -0.14036(4) 0.01952(6) Uani 1 1 d . . . H13A H 0.5736 0.0724 -0.0470 0.029 Uiso 1 1 calc R . . H13B H 0.5571 0.0938 -0.2039 0.029 Uiso 1 1 calc R . . H13C H 0.4560 0.0293 -0.1714 0.029 Uiso 1 1 calc R . . B1 B 0.50549(5) 0.190656(17) 0.06930(4) 0.01149(4) Uani 1 1 d . . . C12 C 0.14473(7) 0.10719(2) -0.28383(4) 0.01954(6) Uani 1 1 d . . . H12A H 0.0168 0.1292 -0.2812 0.029 Uiso 1 1 calc R . . H12B H 0.1133 0.0642 -0.3153 0.029 Uiso 1 1 calc R . . H12C H 0.2150 0.1286 -0.3479 0.029 Uiso 1 1 calc R . . C14 C 0.17383(7) 0.07072(2) -0.04185(5) 0.02048(6) Uani 1 1 d . . . H14A H 0.0444 0.0918 -0.0390 0.031 Uiso 1 1 calc R . . H14B H 0.2613 0.0694 0.0515 0.031 Uiso 1 1 calc R . . H14C H 0.1451 0.0281 -0.0763 0.031 Uiso 1 1 calc R . . 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 0.01083(7) 0.01193(8) 0.00851(7) 0.00057(6) 0.00218(5) 0.00141(6) O1 0.01280(8) 0.01816(10) 0.01464(9) 0.00619(7) 0.00027(6) -0.00286(7) O2 0.02247(10) 0.01419(9) 0.01026(8) -0.00138(6) -0.00026(7) 0.00640(7) C1 0.01165(8) 0.01127(8) 0.00902(8) 0.00124(6) 0.00103(6) 0.00031(6) C2 0.01153(8) 0.01434(10) 0.01310(10) 0.00317(8) 0.00129(7) 0.00101(7) C11 0.01503(9) 0.01361(10) 0.01066(9) -0.00144(7) 0.00037(7) 0.00041(8) C6 0.01421(9) 0.01349(10) 0.01007(9) 0.00115(7) 0.00272(7) 0.00054(7) F1 0.01291(8) 0.02565(13) 0.03190(15) 0.01123(11) 0.00071(8) 0.00534(8) F2 0.02736(12) 0.02658(13) 0.01422(9) 0.00570(8) 0.00908(8) -0.00174(10) C5 0.01764(10) 0.01416(10) 0.00972(9) 0.00184(7) 0.00246(8) -0.00209(8) C4 0.01712(11) 0.01381(10) 0.01291(10) 0.00401(8) -0.00150(8) -0.00165(8) C10 0.01196(9) 0.01863(12) 0.01369(10) -0.00032(9) 0.00248(8) 0.00432(8) C9 0.02103(12) 0.01590(11) 0.01257(10) 0.00027(8) 0.00262(9) 0.00809(10) C8 0.01626(10) 0.01793(12) 0.00993(9) 0.00370(8) 0.00352(8) 0.00075(9) C3 0.01194(9) 0.01424(10) 0.01655(11) 0.00416(8) -0.00101(8) 0.00062(7) C7 0.01600(11) 0.01721(12) 0.01609(11) 0.00661(9) 0.00287(9) -0.00172(9) C13 0.02101(13) 0.01803(13) 0.01775(13) -0.00404(10) 0.00033(10) 0.00665(10) B1 0.01294(10) 0.01128(10) 0.00968(10) 0.00121(8) 0.00119(8) 0.00050(8) C12 0.02149(13) 0.02148(14) 0.01262(11) -0.00339(10) -0.00298(9) 0.00163(11) C14 0.02412(15) 0.01887(14) 0.01742(13) 0.00045(10) 0.00230(11) -0.00771(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C10 1.4973(4) . ? N1 C8 1.5113(4) . ? N1 C11 1.5376(4) . ? N1 B1 1.7645(4) . ? O1 C7 1.4121(4) . ? O1 B1 1.4421(4) . ? O2 C9 1.4134(4) . ? O2 B1 1.4540(4) . ? C1 C6 1.4023(4) . ? C1 C2 1.4028(4) . ? C1 B1 1.6134(4) . ? C2 C3 1.3822(4) . ? C2 H2 0.9500 . ? C11 C14 1.5334(5) . ? C11 C13 1.5335(5) . ? C11 C12 1.5352(5) . ? C6 C5 1.3848(4) . ? C6 H6 0.9500 . ? F1 C3 1.3570(4) . ? F2 C5 1.3517(4) . ? C5 C4 1.3862(5) . ? C4 C3 1.3825(5) . ? C4 H4 0.9500 . ? C10 C9 1.5147(5) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C8 C7 1.5292(5) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? 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 C10 N1 C8 108.79(3) . . ? C10 N1 C11 111.82(3) . . ? C8 N1 C11 110.49(2) . . ? C10 N1 B1 102.21(2) . . ? C8 N1 B1 100.64(2) . . ? C11 N1 B1 121.78(2) . . ? C7 O1 B1 108.58(3) . . ? C9 O2 B1 114.01(3) . . ? C6 C1 C2 117.94(3) . . ? C6 C1 B1 121.40(3) . . ? C2 C1 B1 120.17(3) . . ? C3 C2 C1 119.89(3) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? C14 C11 C13 108.12(3) . . ? C14 C11 C12 108.26(3) . . ? C13 C11 C12 110.33(3) . . ? C14 C11 N1 110.87(3) . . ? C13 C11 N1 109.64(3) . . ? C12 C11 N1 109.60(3) . . ? C5 C6 C1 119.66(3) . . ? C5 C6 H6 120.2 . . ? C1 C6 H6 120.2 . . ? F2 C5 C6 119.01(3) . . ? F2 C5 C4 117.53(3) . . ? C6 C5 C4 123.44(3) . . ? C3 C4 C5 115.64(3) . . ? C3 C4 H4 122.2 . . ? C5 C4 H4 122.2 . . ? N1 C10 C9 104.57(3) . . ? N1 C10 H10A 110.8 . . ? C9 C10 H10A 110.8 . . ? N1 C10 H10B 110.8 . . ? C9 C10 H10B 110.8 . . ? H10A C10 H10B 108.9 . . ? O2 C9 C10 105.18(3) . . ? O2 C9 H9A 110.7 . . ? C10 C9 H9A 110.7 . . ? O2 C9 H9B 110.7 . . ? C10 C9 H9B 110.7 . . ? H9A C9 H9B 108.8 . . ? N1 C8 C7 107.42(3) . . ? N1 C8 H8A 110.2 . . ? C7 C8 H8A 110.2 . . ? N1 C8 H8B 110.2 . . ? C7 C8 H8B 110.2 . . ? H8A C8 H8B 108.5 . . ? F1 C3 C2 118.54(3) . . ? F1 C3 C4 118.05(3) . . ? C2 C3 C4 123.41(3) . . ? O1 C7 C8 105.35(3) . . ? O1 C7 H7A 110.7 . . ? C8 C7 H7A 110.7 . . ? O1 C7 H7B 110.7 . . ? C8 C7 H7B 110.7 . . ? H7A C7 H7B 108.8 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O1 B1 O2 117.06(3) . . ? O1 B1 C1 109.03(3) . . ? O2 B1 C1 109.19(3) . . ? O1 B1 N1 100.01(2) . . ? O2 B1 N1 99.11(2) . . ? C1 B1 N1 122.62(3) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C11 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? 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 C6 C1 C2 C3 0.67(5) . . . . ? B1 C1 C2 C3 172.79(3) . . . . ? C10 N1 C11 C14 -54.83(4) . . . . ? C8 N1 C11 C14 -176.16(3) . . . . ? B1 N1 C11 C14 66.24(4) . . . . ? C10 N1 C11 C13 -174.14(3) . . . . ? C8 N1 C11 C13 64.54(3) . . . . ? B1 N1 C11 C13 -53.06(4) . . . . ? C10 N1 C11 C12 64.62(4) . . . . ? C8 N1 C11 C12 -56.70(3) . . . . ? B1 N1 C11 C12 -174.30(3) . . . . ? C2 C1 C6 C5 -0.24(5) . . . . ? B1 C1 C6 C5 -172.26(3) . . . . ? C1 C6 C5 F2 177.78(3) . . . . ? C1 C6 C5 C4 -0.39(5) . . . . ? F2 C5 C4 C3 -177.64(3) . . . . ? C6 C5 C4 C3 0.57(5) . . . . ? C8 N1 C10 C9 -76.53(3) . . . . ? C11 N1 C10 C9 161.17(3) . . . . ? B1 N1 C10 C9 29.32(3) . . . . ? B1 O2 C9 C10 34.62(4) . . . . ? N1 C10 C9 O2 -39.86(4) . . . . ? C10 N1 C8 C7 100.75(3) . . . . ? C11 N1 C8 C7 -136.14(3) . . . . ? B1 N1 C8 C7 -6.18(3) . . . . ? C1 C2 C3 F1 179.53(3) . . . . ? C1 C2 C3 C4 -0.50(6) . . . . ? C5 C4 C3 F1 179.86(3) . . . . ? C5 C4 C3 C2 -0.11(6) . . . . ? B1 O1 C7 C8 -45.15(4) . . . . ? N1 C8 C7 O1 29.89(4) . . . . ? C7 O1 B1 O2 -67.17(4) . . . . ? C7 O1 B1 C1 168.31(3) . . . . ? C7 O1 B1 N1 38.53(3) . . . . ? C9 O2 B1 O1 91.68(4) . . . . ? C9 O2 B1 C1 -143.89(3) . . . . ? C9 O2 B1 N1 -14.56(4) . . . . ? C6 C1 B1 O1 158.79(3) . . . . ? C2 C1 B1 O1 -13.06(4) . . . . ? C6 C1 B1 O2 29.77(4) . . . . ? C2 C1 B1 O2 -142.08(3) . . . . ? C6 C1 B1 N1 -85.18(4) . . . . ? C2 C1 B1 N1 102.98(3) . . . . ? C10 N1 B1 O1 -130.18(3) . . . . ? C8 N1 B1 O1 -18.11(3) . . . . ? C11 N1 B1 O1 104.26(3) . . . . ? C10 N1 B1 O2 -10.43(3) . . . . ? C8 N1 B1 O2 101.65(3) . . . . ? C11 N1 B1 O2 -135.99(3) . . . . ? C10 N1 B1 C1 109.42(3) . . . . ? C8 N1 B1 C1 -138.50(3) . . . . ? C11 N1 B1 C1 -16.14(4) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.637 _refine_diff_density_min -0.628 _refine_diff_density_rms 0.210 # Attachment '- 1_xd.cif' data_1_xd _database_code_depnum_ccdc_archive 'CCDC 771325' #TrackingRef '- 1_xd.cif' #----------------------------------------------------------------------------# # +CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; 6-tert-butyl-2-(3',5'-difluorophenyl)-(N-B)-1,3,6,2-dioxazaborocan ; _chemical_name_common '3,5-diflurophenyl tert-butyl boronic azaester' _chemical_melting_point 'not measured' _chemical_formula_moiety 'C14 H20 B1 F2 N1 O2' _chemical_formula_sum 'C14 H20 B1 F2 N1 O2' _chemical_formula_weight 283.12 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' _space_group_IT_number 14 loop_ _symmetry_equiv_pos_as_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' _cell_length_a 6.6681(2) _cell_length_b 21.4324(6) _cell_length_c 9.8980(3) _cell_angle_alpha 90.00 _cell_angle_beta 102.551(2) _cell_angle_gamma 90.00 _cell_volume 1380.75(7) _cell_formula_units_Z 4 _cell_measurement_temperature 90(2) _cell_measurement_reflns_used 9441 _cell_measurement_theta_min 3.5468 _cell_measurement_theta_max 52.1998 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description unspecified _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.362 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 600 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.107 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.932 _exptl_absorpt_correction_T_max 1.006 _exptl_absorpt_process_details ; R. H. Blessing, Acta Cryst., 1995, A51, 33-38 ; #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'rotating-anode X-ray source' _diffrn_radiation_source 'TXS rotating anode' _diffrn_ambient_temperature 90(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator 'multi-layer optics' _diffrn_radiation_probe X-ray _diffrn_detector 'APEXII CCD camera' _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Bruker APEXII' _diffrn_measurement_method 'omega scans' _diffrn_orient_matrix_type 'X-axis to radiation source' _diffrn_orient_matrix_UB_11 0.530864E-1 _diffrn_orient_matrix_UB_12 0.433861E-1 _diffrn_orient_matrix_UB_13 -0.499095E-2 _diffrn_orient_matrix_UB_21 -0.933281E-1 _diffrn_orient_matrix_UB_22 0.55535E-2 _diffrn_orient_matrix_UB_23 -0.930111E-1 _diffrn_orient_matrix_UB_31 -0.109894 _diffrn_orient_matrix_UB_32 0.162421E-1 _diffrn_orient_matrix_UB_33 0.451343E-1 _diffrn_reflns_av_sigmaI/netI 0.0348 _diffrn_reflns_number 123017 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 47 _diffrn_reflns_limit_k_min -47 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_theta_max 52.324 _diffrn_reflns_theta_min 2.312 _diffrn_reflns_av_r_equivalents 0.0440 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _reflns_number_total 15927 _reflns_number_gt 12353 _reflns_threshold_expression >2sigma(I) _diffrn_reflns_reduction_process ; Scaled and merged with SORTAV R. H. Blessing, Cryst. Rev., 1987, 1, 3-58 R. H. Blessing, J. Appl. Cryst., 1989, 22, 396-397 ; #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker APEX2 software' _computing_cell_refinement 'Bruker APEX2 software' _computing_data_reduction ; SAINT intergration software, Bruker AXS SORTAV, R. H. Blessing, Acta Cryst., 1995, A51, 33-38 ; _computing_structure_solution ; SHELXS-97, G. M. Sheldrick, Acta. Cryst., 2008, A64, 112-122 ; _computing_structure_refinement ; SHELXS-97, G. M. Sheldrick, Acta. Cryst., 2008, A64, 112-122 XD2006, A. Volkov et al., 2006 ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; calc w2 = 1/[s^2^(Fo^2^)] ; _refine_ls_extinction_method none _refine_ls_number_reflns 11742 _refine_ls_number_parameters 869 _refine_ls_number_restraints 0 _refine_ls_R_factor_gt 0.02 _refine_ls_R_factor_all 0.04 _refine_ls_R_Fsqd_factor 0.022 _refine_ls_wR_factor_ref 0.048 _refine_ls_goodness_of_fit_ref 1.191 _refine_ls_shift/su_max 0.00001 _refine_diff_density_max 0.164 _refine_diff_density_min -0.145 _refine_diff_density_rms 0.031 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_U_iso_or_equiv F(1) 1.04041(5) 0.04699(2) 0.32477(5) 1 4 0.024 F(2) 0.44081(6) 0.07373(2) 0.49316(3) 1 4 0.022 O(1) 0.67914(4) 0.211818(14) 0.01660(3) 1 4 0.015 O(2) 0.38748(4) 0.238008(13) 0.12301(2) 1 4 0.016 N(1) 0.33087(3) 0.173860(10) -0.087736(19) 1 4 0.010 C(1) 0.58181(3) 0.138590(10) 0.18703(2) 1 4 0.011 C(2) 0.77756(3) 0.111876(11) 0.20271(2) 1 4 0.013 C(11) 0.28442(3) 0.106515(11) -0.13843(2) 1 4 0.013 C(6) 0.46771(3) 0.124612(11) 0.28657(2) 1 4 0.012 C(5) 0.54958(4) 0.085248(11) 0.39563(2) 1 4 0.014 C(4) 0.74184(4) 0.057818(12) 0.41262(2) 1 4 0.015 C(10) 0.14122(3) 0.207241(13) -0.06994(2) 1 4 0.014 C(9) 0.22019(4) 0.261884(13) 0.02383(3) 1 4 0.016 C(8) 0.42660(4) 0.209994(13) -0.18855(2) 1 4 0.014 C(3) 0.85130(3) 0.072565(11) 0.31307(3) 1 4 0.014 C(7) 0.60617(4) 0.247390(13) -0.10390(3) 1 4 0.016 C(13) 0.48578(5) 0.072365(15) -0.14033(3) 1 4 0.019 C(12) 0.14474(5) 0.107161(16) -0.28380(3) 1 4 0.019 C(14) 0.17393(5) 0.070695(16) -0.04181(3) 1 4 0.020 B(1) 0.50549(3) 0.190623(11) 0.06928(2) 1 4 0.011 H(2) 0.876417 0.122364 0.132149 1 4 0.031 H(6) 0.317945 0.145094 0.282146 1 4 0.030 H(4) 0.800897 0.026171 0.497212 1 4 0.033 H(10A) 0.051475 0.176938 -0.016868 1 4 0.032 H(10B) 0.047203 0.219949 -0.170837 1 4 0.031 H(9A) 0.263267 0.30112 -0.034298 1 4 0.034 H(9B) 0.103445 0.278778 0.07702 1 4 0.038 H(8A) 0.311312 0.239449 -0.253974 1 4 0.030 H(8B) 0.486835 0.176268 -0.252325 1 4 0.032 H(7A) 0.729604 0.254073 -0.159141 1 4 0.038 H(7B) 0.55841 0.293745 -0.077571 1 4 0.035 H(13A) 0.583076 0.071386 -0.040362 1 4 0.036 H(13B) 0.575433 0.091551 -0.206232 1 4 0.041 H(13C) 0.456106 0.025678 -0.173771 1 4 0.044 H(12A) 0.006348 0.131485 -0.284264 1 4 0.041 H(12B) 0.105705 0.060807 -0.316234 1 4 0.047 H(12C) 0.220444 0.126983 -0.357134 1 4 0.041 H(14A) 0.020279 0.085897 -0.051866 1 4 0.041 H(14B) 0.249483 0.0754 0.063459 1 4 0.035 H(14C) 0.171692 0.023132 -0.071089 1 4 0.043 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 F(1) 0.01291(12) 0.02549(16) 0.03094(17) 0.00487(9) 0.00032(10) 0.01105(13) F(2) 0.02647(15) 0.02653(16) 0.01378(12) -0.00152(12) 0.00832(10) 0.00563(10) O(1) 0.01228(10) 0.01815(11) 0.01441(11) -0.00292(7) 0.00027(6) 0.00584(7) O(2) 0.02226(11) 0.01395(11) 0.00989(10) 0.00613(7) -0.00006(7) -0.00152(6) N(1) 0.01047(9) 0.01174(10) 0.00794(9) 0.00139(5) 0.00193(5) 0.00052(5) C(1) 0.01115(9) 0.01122(10) 0.00869(9) 0.00055(5) 0.00107(5) 0.00158(5) C(2) 0.01091(10) 0.01437(10) 0.01284(10) 0.00120(6) 0.00138(5) 0.00346(6) C(11) 0.01451(10) 0.01355(10) 0.01030(10) 0.00052(6) 0.00029(5) -0.00135(6) C(6) 0.01368(10) 0.01347(10) 0.00970(10) 0.00066(6) 0.00280(6) 0.00135(6) C(5) 0.01701(10) 0.01402(10) 0.00938(10) -0.00177(6) 0.00217(6) 0.00216(6) C(4) 0.01667(10) 0.01370(11) 0.01249(10) -0.00140(6) -0.00145(6) 0.00428(6) C(10) 0.01169(10) 0.01836(11) 0.01319(10) 0.00414(6) 0.00227(6) -0.00026(7) C(9) 0.02074(11) 0.01550(11) 0.01227(11) 0.00807(7) 0.00272(7) 0.00027(7) C(8) 0.01580(10) 0.01769(11) 0.00963(10) 0.00083(7) 0.00328(6) 0.00354(6) C(3) 0.01167(10) 0.01415(10) 0.01585(11) 0.00060(6) -0.00094(6) 0.00455(7) C(7) 0.01569(10) 0.01688(11) 0.01587(11) -0.00166(7) 0.00297(7) 0.00651(7) C(13) 0.02063(12) 0.01788(12) 0.01734(12) 0.00653(8) 0.00022(8) -0.00395(8) C(12) 0.02101(12) 0.02127(13) 0.01224(11) 0.00157(9) -0.00277(7) -0.00327(8) C(14) 0.02375(13) 0.01873(13) 0.01699(12) -0.00771(9) 0.00223(8) 0.00034(8) B(1) 0.01251(10) 0.01093(10) 0.00954(10) 0.00065(5) 0.00123(5) 0.00135(5) H(2) 0.021857 0.041352 0.032521 0.003378 0.011506 0.012476 H(6) 0.025052 0.038222 0.028257 0.010026 0.010875 0.005573 H(4) 0.036927 0.030769 0.028897 0.002602 0.0003 0.01526 H(10A) 0.027937 0.036956 0.033283 0.000971 0.014324 0.004973 H(10B) 0.030121 0.039547 0.021379 0.010329 -0.00188 0.003074 H(9A) 0.046369 0.026561 0.027423 0.002899 0.002558 0.00621 H(9B) 0.040704 0.046074 0.030217 0.019974 0.01218 -0.004216 H(8A) 0.027625 0.032846 0.027925 0.005704 0.00009 0.009332 H(8B) 0.034673 0.035764 0.028706 0.005052 0.015275 -0.003892 H(7A) 0.027257 0.054638 0.033547 -0.005417 0.00982 0.015122 H(7B) 0.041938 0.024788 0.032722 0.001088 -0.001219 0.003431 H(13A) 0.034893 0.047044 0.021987 0.012638 0.000244 -0.00422 H(13B) 0.044203 0.047022 0.03757 0.013222 0.022796 0.009607 H(13C) 0.054564 0.02604 0.049362 0.005366 0.006763 -0.014759 H(12A) 0.031546 0.053242 0.03374 0.009364 -0.0023 -0.003489 H(12B) 0.065739 0.02934 0.035949 -0.006818 -0.009598 -0.00835 H(12C) 0.045582 0.054379 0.023256 -0.004831 0.006728 0.002822 H(14A) 0.021822 0.051811 0.047176 0.001063 0.004908 0.013181 H(14B) 0.033385 0.045863 0.021052 -0.012398 -0.001614 0.000985 H(14C) 0.058196 0.024055 0.044562 -0.010277 0.009241 -0.005843 #----------------------------------------------------------------------------# # MULTIPOLE PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_rho_multipole_atom_label _atom_rho_multipole_coeff_Pv _atom_rho_multipole_coeff_P00 _atom_rho_multipole_coeff_P11 _atom_rho_multipole_coeff_P1-1 _atom_rho_multipole_coeff_P10 _atom_rho_multipole_coeff_P20 _atom_rho_multipole_coeff_P21 _atom_rho_multipole_coeff_P2-1 _atom_rho_multipole_coeff_P22 _atom_rho_multipole_coeff_P2-2 _atom_rho_multipole_coeff_P30 _atom_rho_multipole_coeff_P31 _atom_rho_multipole_coeff_P3-1 _atom_rho_multipole_coeff_P32 _atom_rho_multipole_coeff_P3-2 _atom_rho_multipole_coeff_P33 _atom_rho_multipole_coeff_P3-3 _atom_rho_multipole_coeff_P40 _atom_rho_multipole_coeff_P41 _atom_rho_multipole_coeff_P4-1 _atom_rho_multipole_coeff_P42 _atom_rho_multipole_coeff_P4-2 _atom_rho_multipole_coeff_P43 _atom_rho_multipole_coeff_P4-3 _atom_rho_multipole_coeff_P44 _atom_rho_multipole_coeff_P4-4 _atom_rho_multipole_kappa _atom_rho_multipole_kappa_prime0 _atom_rho_multipole_kappa_prime1 _atom_rho_multipole_kappa_prime2 _atom_rho_multipole_kappa_prime3 _atom_rho_multipole_kappa_prime4 _atom_rho_multipole_radial_slater_n0 _atom_rho_multipole_radial_slater_zeta0 _atom_rho_multipole_radial_slater_n1 _atom_rho_multipole_radial_slater_zeta1 _atom_rho_multipole_radial_slater_n2 _atom_rho_multipole_radial_slater_zeta2 _atom_rho_multipole_radial_slater_n3 _atom_rho_multipole_radial_slater_zeta3 _atom_rho_multipole_radial_slater_n4 _atom_rho_multipole_radial_slater_zeta4 F(1) 7.095(15) 0 -0.079(11) 0.047(10) 0.005(9) -0.100(10) 0.053(11) 0.005(10) 0.006(12) -0.050(12) -0.035(7) 0.033(7) 0.021(6) 0.005(7) -0.020(7) -0.012(8) 0.040(8) -0.018(10) -0.019(9) 0.019(8) -0.020(9) -0.008(9) 0.029(10) 0.001(10) -0.013(10) 0.011(10) 1 1 1 1 1 1 2 5.1078857142857 2 5.1078857142857 2 5.1078857142857 3 5.1078857142857 4 5.1078857142857 F(2) 7.074(15) 0 0.084(10) -0.015(10) -0.018(8) -0.070(10) -0.027(10) 0.006(10) -0.044(12) 0.061(12) -0.006(7) -0.034(6) 0.007(6) 0.060(7) 0.043(7) -0.039(8) 0.053(8) 0.020(9) -0.013(8) 0.014(8) -0.017(8) 0.015(8) 0.005(9) -0.006(9) 0.010(10) 0.015(9) 1 1 1 1 1 1 2 5.1078857142857 2 5.1078857142857 2 5.1078857142857 3 5.1078857142857 4 5.1078857142857 O(1) 6.114(18) 0 -0.007(9) -0.000(8) -0.050(8) -0.067(9) 0.054(9) 0.034(8) 0.008(8) -0.011(8) 0.066(7) 0.004(7) -0.034(6) -0.004(7) -0.015(7) 0.038(7) -0.015(7) 0.028(9) 0.009(9) 0.010(8) 0.024(8) -0.008(8) -0.006(8) 0.000(8) -0.001(8) 0.018(8) 1 1 1 1 1 1 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466 O(2) 6.106(19) 0 -0.045(9) -0.011(8) -0.045(9) -0.063(9) -0.001(9) 0.045(8) 0.001(8) 0.018(8) 0.052(7) 0.020(7) -0.012(7) 0.050(7) -0.004(7) -0.053(7) -0.016(7) 0.018(9) 0.016(9) 0.022(8) -0.004(9) -0.000(9) -0.014(9) -0.011(8) -0.011(8) -0.008(8) 1 1 1 1 1 1 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466 N(1) 5.07(2) 0 0.053(9) -0.021(8) -0.019(8) -0.043(8) -0.020(8) 0.017(8) 0.047(8) -0.056(8) 0.135(8) -0.013(7) -0.006(7) 0.011(7) -0.022(8) 0.024(7) -0.112(7) 0.026(10) -0.018(9) -0.002(9) -0.028(9) 0.028(9) -0.005(9) 0.029(9) -0.006(9) 0.010(9) 1 1 1 1 1 1 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936 C(1) 4.10(4) 0 -0.008(12) -0.015(13) -0.012(12) 0.097(11) -0.002(10) 0.015(11) -0.173(11) -0.043(10) 0.189(12) -0.010(11) -0.013(12) 0.147(12) -0.002(11) 0.018(11) -0.003(11) 0.028(16) -0.031(13) 0.010(15) -0.036(15) -0.018(14) 0.001(14) 0.035(14) 0.017(13) 0.002(13) 1 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(2) 4.02(4) 0 -0.016(13) -0.024(14) -0.000(15) 0.081(12) -0.027(11) 0.021(11) -0.152(11) 0.056(11) 0.194(13) -0.022(12) -0.041(12) 0.105(12) -0.013(12) -0.005(12) -0.016(12) 0.041(16) -0.044(14) 0.032(16) -0.002(16) 0.012(15) -0.002(14) 0.005(15) 0.010(14) -0.019(14) 1 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(11) 4.02(3) 0 0.037(12) -0.011(12) -0.017(12) 0.007(11) -0.065(11) -0.050(11) -0.013(11) -0.075(10) 0.190(12) -0.026(12) 0.010(12) 0.002(12) -0.003(12) 0.013(12) -0.164(12) -0.005(16) -0.006(15) -0.081(16) 0.007(16) 0.005(15) -0.006(15) 0.076(15) 0.004(15) 0.025(15) 1 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(6) 4.07(4) 0 0.001(12) -0.018(13) -0.015(15) 0.074(12) 0.031(11) 0.005(12) -0.137(11) -0.042(10) 0.218(13) 0.015(12) -0.018(13) 0.104(12) 0.015(11) 0.019(11) -0.014(11) 0.012(16) -0.019(15) 0.022(17) -0.037(16) -0.031(15) 0.012(14) -0.019(14) 0.014(14) 0.024(14) 1 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(5) 4.03(4) 0 0.008(12) 0.023(14) -0.134(12) -0.018(11) 0.003(10) -0.013(11) -0.184(12) -0.076(11) 0.293(13) 0.026(11) -0.022(12) 0.110(13) 0.034(12) 0.008(12) -0.014(12) 0.088(17) 0.039(14) 0.033(17) -0.046(15) -0.031(15) -0.004(15) -0.027(15) 0.023(15) 0.019(15) 1 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(4) 4.16(4) 0 0.023(13) 0.001(15) 0.002(15) 0.084(13) -0.062(11) 0.008(13) -0.136(12) -0.006(12) 0.233(14) 0.005(12) 0.025(14) 0.132(13) 0.030(12) 0.010(12) 0.021(12) -0.006(17) -0.004(15) -0.003(18) 0.002(17) -0.001(17) 0.022(15) 0.011(16) 0.065(15) 0.020(15) 1 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(10) 4.22(4) 0 0.039(13) 0.039(15) 0.029(16) 0.018(13) -0.013(12) -0.028(12) -0.094(11) -0.075(12) 0.245(13) -0.007(13) -0.009(14) -0.011(12) 0.010(13) -0.007(12) -0.198(12) 0.052(16) -0.013(16) 0.009(16) -0.001(16) -0.014(17) 0.035(15) 0.109(15) -0.030(15) 0.026(15) 1 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(9) 4.07(5) 0 -0.076(14) 0.012(15) 0.069(15) 0.032(13) 0.009(12) -0.022(12) -0.029(12) 0.001(13) 0.239(13) -0.038(13) -0.003(14) -0.028(13) 0.054(13) 0.019(14) -0.208(13) 0.046(17) -0.031(16) -0.028(16) -0.008(17) 0.040(17) 0.025(16) 0.078(16) -0.011(16) -0.027(17) 1 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(8) 4.21(4) 0 -0.072(13) 0.047(15) 0.032(15) 0.028(13) 0.020(12) 0.003(12) -0.077(11) 0.080(11) 0.246(13) -0.001(13) 0.011(14) 0.005(12) -0.014(12) 0.023(12) -0.188(12) 0.032(16) -0.020(16) -0.034(16) 0.014(17) 0.015(16) -0.018(15) 0.055(15) -0.010(15) -0.029(15) 1 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(3) 4.05(3) 0 0.001(12) 0.010(14) -0.122(13) -0.026(12) -0.047(11) 0.000(12) -0.203(12) 0.020(11) 0.319(14) -0.009(12) 0.007(12) 0.150(13) -0.016(12) -0.001(12) 0.000(12) 0.072(17) -0.014(15) 0.008(17) -0.062(16) -0.010(15) -0.012(15) -0.003(15) 0.013(14) -0.020(14) 1 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(7) 3.97(5) 0 0.046(13) 0.068(16) -0.018(15) 0.046(13) -0.003(12) -0.027(12) -0.006(12) -0.017(13) 0.244(13) 0.026(13) 0.011(14) -0.039(13) -0.029(13) -0.006(14) -0.208(13) 0.071(17) -0.021(16) -0.041(16) 0.003(16) 0.010(17) 0.018(16) 0.089(16) 0.005(17) -0.005(16) 1 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(13) 4.34(6) 0 -0.056(18) -0.046(18) 0.014(18) 0.072(15) 0.002(14) 0.017(15) 0.025(15) 0.053(14) 0.207(15) 0.033(15) 0.028(16) -0.025(15) 0.029(15) 0.023(15) -0.219(14) 0.057(18) 0.034(18) 0.035(18) -0.007(19) 0.019(19) 0.045(18) 0.066(17) 0.011(17) -0.011(17) 1 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(12) 4.20(6) 0 -0.031(17) 0.026(19) -0.061(18) -0.058(16) 0.003(14) -0.017(15) 0.008(14) 0.020(14) 0.212(15) 0.002(16) -0.012(17) 0.041(15) 0.001(14) 0.011(15) -0.173(13) 0.012(18) -0.005(18) 0.013(18) -0.009(19) -0.044(19) -0.004(18) 0.032(16) -0.011(17) -0.023(17) 1 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(14) 4.26(6) 0 0.051(18) 0.016(18) -0.038(19) -0.052(16) 0.015(14) -0.030(15) -0.028(15) 0.017(14) 0.204(15) -0.094(16) -0.032(17) -0.000(15) 0.004(15) 0.027(15) -0.200(14) 0.024(19) -0.029(18) -0.004(19) -0.00(2) 0.053(19) 0.002(18) 0.065(17) -0.002(17) -0.066(18) 1 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 B(1) 3.05(5) 0 -0.034(15) 0.025(16) 0.016(15) 0.066(14) 0.055(13) -0.064(13) -0.005(13) 0.096(14) 0.341(19) -0.025(16) 0.033(16) 0.072(16) -0.120(17) 0.022(16) -0.224(17) 0.12(2) -0.01(2) -0.01(2) -0.08(2) -0.02(2) 0.03(2) 0.13(2) 0.04(2) 0.00(2) 1 1 1 1 1 1 2 2.5246 2 2.5246 2 2.5246 3 2.5246 4 2.5246 H(2) 0.87(2) 0 -0.024(15) -0.013(14) 0.168(14) 0.07(2) -0.019(18) -0.001(18) -0.018(19) -0.024(18) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(6) 0.91(2) 0 -0.009(15) -0.024(13) 0.161(15) 0.07(2) 0.006(19) 0.016(18) -0.014(18) -0.012(17) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(4) 0.86(2) 0 0.022(14) -0.025(15) 0.136(15) 0.06(2) 0.000(18) 0.003(18) -0.020(18) 0.006(19) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(10A) 0.89(2) 0 0.025(14) -0.014(15) 0.147(15) 0.05(2) 0.006(19) 0.021(19) 0.010(18) -0.014(19) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(10B) 0.87(2) 0 0.046(14) -0.015(15) 0.103(15) 0.02(2) 0.049(19) 0.00(2) -0.020(18) 0.015(18) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(9A) 0.94(2) 0 0.032(16) -0.032(15) 0.145(17) 0.05(2) 0.05(2) -0.01(2) 0.028(19) -0.004(19) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(9B) 0.90(2) 0 -0.009(16) -0.001(16) 0.121(15) 0.00(2) -0.001(19) 0.01(2) -0.00(2) 0.02(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(8A) 0.86(2) 0 0.007(14) 0.029(15) 0.151(15) 0.03(2) 0.010(19) 0.004(19) -0.037(18) -0.016(18) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(8B) 0.85(2) 0 -0.032(14) 0.000(15) 0.125(15) 0.05(2) -0.053(19) 0.005(19) -0.009(18) 0.002(19) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(7A) 0.91(2) 0 -0.051(15) -0.046(16) 0.138(15) 0.09(2) -0.011(19) -0.03(2) -0.011(19) 0.07(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(7B) 0.96(2) 0 0.001(15) -0.031(16) 0.125(17) 0.03(2) -0.00(2) -0.02(2) 0.066(19) 0.032(19) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(13A) 0.78(2) 0 0.016(16) 0.033(18) 0.079(17) -0.01(2) 0.03(2) 0.07(2) -0.04(2) 0.01(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(13B) 0.81(3) 0 0.056(18) 0.025(18) 0.072(18) -0.03(2) -0.03(2) 0.04(2) -0.01(2) 0.03(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(13C) 0.93(3) 0 -0.010(18) -0.029(18) 0.120(18) 0.05(2) 0.03(2) -0.02(2) -0.04(2) -0.06(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(12A) 0.90(3) 0 -0.001(17) 0.034(18) 0.053(19) -0.00(2) -0.02(2) 0.04(2) -0.04(2) 0.01(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(12B) 0.98(3) 0 -0.033(17) -0.040(19) 0.138(19) 0.08(3) -0.00(2) -0.01(2) -0.01(2) -0.03(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(12C) 0.90(3) 0 0.056(18) -0.056(18) 0.072(19) 0.01(2) 0.05(2) -0.03(2) -0.00(2) 0.01(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(14A) 0.93(3) 0 0.013(17) 0.071(19) 0.084(19) 0.07(3) 0.07(2) 0.03(2) 0.02(2) 0.02(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(14B) 0.76(2) 0 -0.014(16) 0.010(18) 0.077(16) -0.07(2) -0.06(2) -0.01(2) 0.02(2) 0.03(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(14C) 0.96(3) 0 -0.027(18) 0.034(18) 0.101(18) 0.07(2) -0.03(2) 0.05(2) -0.04(2) 0.05(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 loop_ _atom_local_axes_atom_label _atom_local_axes_atom0 _atom_local_axes_ax1 _atom_local_axes_atom1 _atom_local_axes_atom2 _atom_local_axes_ax2 F(1) C(3) Z F(1) C(4) Y F(2) C(5) Z F(2) C(4) Y O(1) C(7) Z O(1) B(1) Y O(2) C(9) Z O(2) B(1) Y N(1) C(10) Z N(1) C(8) Y C(1) C(6) Z C(1) C(2) Y C(2) H(2) Z C(2) C(3) Y C(11) C(14) Z C(11) C(13) Y C(6) H(6) Z C(6) C(5) Y C(5) F(2) Z C(5) C(6) Y C(4) H(4) Z C(4) C(3) Y C(10) H(10A) Z C(10) H(10B) Y C(9) H(9B) Z C(9) H(9A) Y C(8) H(8B) Z C(8) H(8A) Y C(3) F(1) Z C(3) C(2) Y C(7) H(7A) Z C(7) H(7B) Y C(13) H(13A) Z C(13) H(13C) Y C(12) H(12B) Z C(12) H(12A) Y C(14) H(14C) Z C(14) H(14B) Y B(1) O(1) Z B(1) O(2) Y H(2) C(2) Z H(2) C(3) Y H(6) C(6) Z H(6) C(5) Y H(4) C(4) Z H(4) C(3) Y H(10A) C(10) Z H(10A) H(10B) Y H(10B) C(10) Z H(10B) H(10A) Y H(9A) C(9) Z H(9A) H(9B) Y H(9B) C(9) Z H(9B) H(9A) Y H(8A) C(8) Z H(8A) H(8B) Y H(8B) C(8) Z H(8B) H(8A) Y H(7A) C(7) Z H(7A) H(7B) Y H(7B) C(7) Z H(7B) H(7A) Y H(13A) C(13) Z H(13A) H(13B) Y H(13B) C(13) Z H(13B) H(13C) Y H(13C) C(13) Z H(13C) H(13B) Y H(12A) C(12) Z H(12A) H(12B) Y H(12B) C(12) Z H(12B) H(12A) Y H(12C) C(12) Z H(12C) H(12B) Y H(14A) C(14) Z H(14A) H(14C) Y H(14B) C(14) Z H(14B) H(14C) Y H(14C) C(14) Z H(14C) H(14B) Y #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag F(1) C(3) 1.3567(4) 1_555 1_555 yes F(2) C(5) 1.3502(4) 1_555 1_555 yes O(1) C(7) 1.4101(3) 1_555 1_555 yes O(1) B(1) 1.4428(3) 1_555 1_555 yes O(2) C(9) 1.4121(3) 1_555 1_555 yes O(2) B(1) 1.4544(3) 1_555 1_555 yes C(1) C(2) 1.4027(3) 1_555 1_555 yes C(1) C(6) 1.4018(3) 1_555 1_555 yes C(1) B(1) 1.6134(3) 1_555 1_555 yes C(2) C(3) 1.3826(3) 1_555 1_555 yes C(2) H(2) 1.0830 1_555 1_555 yes C(11) C(13) 1.5329(3) 1_555 1_555 yes C(11) C(12) 1.5348(3) 1_555 1_555 yes C(11) C(14) 1.5339(4) 1_555 1_555 yes C(6) C(5) 1.3853(3) 1_555 1_555 yes C(6) H(6) 1.0830 1_555 1_555 yes C(5) C(4) 1.3870(3) 1_555 1_555 yes C(4) C(3) 1.3842(3) 1_555 1_555 yes C(4) H(4) 1.0830 1_555 1_555 yes C(10) C(9) 1.5159(4) 1_555 1_555 yes C(10) H(10A) 1.0920 1_555 1_555 yes C(10) H(10B) 1.0920 1_555 1_555 yes C(9) H(9A) 1.0920 1_555 1_555 yes C(9) H(9B) 1.0920 1_555 1_555 yes C(8) C(7) 1.5304(4) 1_555 1_555 yes C(8) H(8A) 1.0920 1_555 1_555 yes C(8) H(8B) 1.0920 1_555 1_555 yes C(7) H(7A) 1.0920 1_555 1_555 yes C(7) H(7B) 1.0920 1_555 1_555 yes C(13) H(13A) 1.0590 1_555 1_555 yes C(13) H(13B) 1.0590 1_555 1_555 yes C(13) H(13C) 1.0590 1_555 1_555 yes C(12) H(12A) 1.0590 1_555 1_555 yes C(12) H(12B) 1.0590 1_555 1_555 yes C(12) H(12C) 1.0590 1_555 1_555 yes C(14) H(14A) 1.0590 1_555 1_555 yes C(14) H(14B) 1.0590 1_555 1_555 yes C(14) H(14C) 1.0590 1_555 1_555 yes 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C(7) O(1) B(1) 108.63(2) 1_555 1_555 1_555 yes C(9) O(2) B(1) 114.03(2) 1_555 1_555 1_555 yes C(2) C(1) C(6) 117.980(18) 1_555 1_555 1_555 yes C(2) C(1) B(1) 120.126(17) 1_555 1_555 1_555 yes C(6) C(1) B(1) 121.413(18) 1_555 1_555 1_555 yes C(1) C(2) C(3) 119.92(2) 1_555 1_555 1_555 yes C(1) C(2) H(2) 121.742 1_555 1_555 1_555 yes C(3) C(2) H(2) 118.306 1_555 1_555 1_555 yes C(13) C(11) C(12) 110.34(2) 1_555 1_555 1_555 yes C(13) C(11) C(14) 108.02(2) 1_555 1_555 1_555 yes C(12) C(11) C(14) 108.25(2) 1_555 1_555 1_555 yes C(1) C(6) C(5) 119.71(2) 1_555 1_555 1_555 yes C(1) C(6) H(6) 121.435 1_555 1_555 1_555 yes C(5) C(6) H(6) 118.824 1_555 1_555 1_555 yes F(2) C(5) C(6) 119.12(3) 1_555 1_555 1_555 yes F(2) C(5) C(4) 117.50(3) 1_555 1_555 1_555 yes C(6) C(5) C(4) 123.36(2) 1_555 1_555 1_555 yes C(5) C(4) C(3) 115.68(2) 1_555 1_555 1_555 yes C(5) C(4) H(4) 122.03 1_555 1_555 1_555 yes C(3) C(4) H(4) 122.27 1_555 1_555 1_555 yes C(9) C(10) H(10A) 108.59 1_555 1_555 1_555 yes C(9) C(10) H(10B) 114.91 1_555 1_555 1_555 yes H(10A) C(10) H(10B) 108.82 1_555 1_555 1_555 yes O(2) C(9) C(10) 105.22(2) 1_555 1_555 1_555 yes O(2) C(9) H(9A) 112.76 1_555 1_555 1_555 yes O(2) C(9) H(9B) 108.86 1_555 1_555 1_555 yes C(10) C(9) H(9A) 111.62 1_555 1_555 1_555 yes C(10) C(9) H(9B) 111.23 1_555 1_555 1_555 yes H(9A) C(9) H(9B) 107.18 1_555 1_555 1_555 yes C(7) C(8) H(8A) 112.84 1_555 1_555 1_555 yes C(7) C(8) H(8B) 108.71 1_555 1_555 1_555 yes H(8A) C(8) H(8B) 109.87 1_555 1_555 1_555 yes F(1) C(3) C(2) 118.56(3) 1_555 1_555 1_555 yes F(1) C(3) C(4) 118.10(3) 1_555 1_555 1_555 yes C(2) C(3) C(4) 123.34(2) 1_555 1_555 1_555 yes O(1) C(7) C(8) 105.37(2) 1_555 1_555 1_555 yes O(1) C(7) H(7A) 109.59 1_555 1_555 1_555 yes O(1) C(7) H(7B) 110.79 1_555 1_555 1_555 yes C(8) C(7) H(7A) 112.32 1_555 1_555 1_555 yes C(8) C(7) H(7B) 111.90 1_555 1_555 1_555 yes H(7A) C(7) H(7B) 106.91 1_555 1_555 1_555 yes C(11) C(13) H(13A) 111.00 1_555 1_555 1_555 yes C(11) C(13) H(13B) 115.81 1_555 1_555 1_555 yes C(11) C(13) H(13C) 110.51 1_555 1_555 1_555 yes H(13A) C(13) H(13B) 105.66 1_555 1_555 1_555 yes H(13A) C(13) H(13C) 107.95 1_555 1_555 1_555 yes H(13B) C(13) H(13C) 105.46 1_555 1_555 1_555 yes C(11) C(12) H(12A) 111.05 1_555 1_555 1_555 yes C(11) C(12) H(12B) 109.56 1_555 1_555 1_555 yes C(11) C(12) H(12C) 111.32 1_555 1_555 1_555 yes H(12A) C(12) H(12B) 107.70 1_555 1_555 1_555 yes H(12A) C(12) H(12C) 110.14 1_555 1_555 1_555 yes H(12B) C(12) H(12C) 106.91 1_555 1_555 1_555 yes C(11) C(14) H(14A) 111.92 1_555 1_555 1_555 yes C(11) C(14) H(14B) 112.06 1_555 1_555 1_555 yes C(11) C(14) H(14C) 106.93 1_555 1_555 1_555 yes H(14A) C(14) H(14B) 107.87 1_555 1_555 1_555 yes H(14A) C(14) H(14C) 108.34 1_555 1_555 1_555 yes H(14B) C(14) H(14C) 109.65 1_555 1_555 1_555 yes O(1) B(1) O(2) 116.92(2) 1_555 1_555 1_555 yes O(1) B(1) C(1) 109.072(18) 1_555 1_555 1_555 yes O(2) B(1) C(1) 109.227(18) 1_555 1_555 1_555 yes