Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2001 data_global _journal_coden_Cambridge 186 _publ_contact_author 'Prof Todd Marder' _publ_contact_author_address ; Prof Todd Marder Department of Chemistry University of Durham South Road Durham DH1 3LE UK ; loop_ _publ_author_name 'Coapes, R. Benjamin' 'Souza, Fabio E. S.' 'Fox, Mark A.' 'Batsanov, Andrei S.' 'Goeta, Andres E.' 'Yufit, Dmitrii S.' 'Leech, Michael A.' 'Howard, Judith A. K.' 'Scott, Andrew J.' 'Clegg, William' 'Marder, Todd B.' _journal_name_full 'Journal of the Chemical Society, Dalton Transaction' _journal_volume '?' _journal_page_first '?' _journal_page_last '?' _journal_year '?' _ccdc_journal_depnumber '?' _publ_section_title ; Phosphine promoted substituent redistribution reactions of B-chlorocatechol borane: molecular structures of ClBcat, BrBcat, and L.ClBcat (cat = 1,2-O~2~C~6~H~4~; L = PMe~3~, PEt~3~, PBu^t^~3~, PCy~3~, NEt~3~). ; #====================================================================== data_1 _database_code_CSD 154920 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-chloro-1,3,2-benzodioxaborole ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H4 B Cl O2' _chemical_formula_weight 154.35 _ccdc_compound_id '1' _ccdc_biological_activity '?' _ccdc_polymorph '?' _ccdc_disorder 'none' _ccdc_comments '?' 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' 'B' 'B' 0.0013 0.0007 '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' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 10.5584(8) _cell_length_b 9.8180(8) _cell_length_c 7.1370(5) _cell_angle_alpha 90.00 _cell_angle_beta 118.75(1) _cell_angle_gamma 90.00 _cell_volume 648.62(9) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2028 _cell_measurement_theta_min 6.0 _cell_measurement_theta_max 58.1 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.581 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 312 _exptl_absorpt_coefficient_mu 0.506 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.8155 _exptl_absorpt_correction_T_max 0.9325 _exptl_absorpt_process_details 'SADABS (G.M.Sheldrick, 1998)' _exptl_special_details ; Five sets of \w scans (each scan 0.3\% in \w), each set at different \f and 2\q angles, nominally covered whole sphere of reciprocal space. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'SMART 1K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% 0 _diffrn_reflns_number 2888 _diffrn_reflns_av_R_equivalents 0.0319 _diffrn_reflns_av_sigmaI/netI 0.0191 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.0 _diffrn_reflns_theta_max 27.5 _reflns_number_total 753 _reflns_number_gt 684 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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. ; _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^)+(0.0500P)^2^+0.5000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refxyz _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 753 _refine_ls_number_parameters 53 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0383 _refine_ls_R_factor_gt 0.0345 _refine_ls_wR_factor_ref 0.0950 _refine_ls_wR_factor_gt 0.0924 _refine_ls_goodness_of_fit_ref 1.108 _refine_ls_restrained_S_all 1.108 _refine_ls_shift/su_max 0.000 _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 Cl1 Cl 1.0000 0.09423(6) 0.7500 0.0346(2) Uani 1 2 d S . . O1 O 0.88279(11) 0.34848(11) 0.72328(17) 0.0246(3) Uani 1 1 d . . . B1 B 1.0000 0.2719(3) 0.7500 0.0255(5) Uani 1 2 d S . . C1 C 0.92954(14) 0.48263(16) 0.7343(2) 0.0217(3) Uani 1 1 d . . . C2 C 0.85551(16) 0.60175(17) 0.7191(2) 0.0259(4) Uani 1 1 d . . . H2 H 0.759(2) 0.6006(18) 0.700(3) 0.031 Uiso 1 1 d . . . C3 C 0.92959(16) 0.72326(17) 0.7357(2) 0.0270(4) Uani 1 1 d . . . H3 H 0.882(2) 0.810(2) 0.727(3) 0.032 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 Cl1 0.0327(3) 0.0282(3) 0.0509(4) 0.000 0.0265(3) 0.000 O1 0.0190(6) 0.0292(6) 0.0290(6) 0.0016(4) 0.0143(5) -0.0006(4) B1 0.0218(11) 0.0311(12) 0.0273(12) 0.000 0.0149(10) 0.000 C1 0.0169(7) 0.0299(8) 0.0194(7) 0.0005(5) 0.0097(5) -0.0014(5) C2 0.0186(7) 0.0365(9) 0.0235(7) 0.0031(6) 0.0109(6) 0.0036(6) C3 0.0247(8) 0.0308(8) 0.0226(8) 0.0010(6) 0.0091(6) 0.0042(6) _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 Cl1 B1 1.744(3) . ? O1 B1 1.3807(17) . ? O1 C1 1.3954(19) . ? B1 O1 1.3807(17) 2_756 ? C1 C2 1.381(2) . ? C1 C1 1.394(3) 2_756 ? C2 C3 1.400(2) . ? C3 C3 1.400(3) 2_756 ? 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 O1 C1 103.71(13) . . ? O1 B1 O1 114.0(2) 2_756 . ? O1 B1 Cl1 123.00(10) 2_756 . ? O1 B1 Cl1 123.00(10) . . ? C2 C1 C1 122.16(9) . 2_756 ? C2 C1 O1 128.55(13) . . ? C1 C1 O1 109.29(7) 2_756 . ? C1 C2 C3 116.29(14) . . ? C3 C3 C2 121.55(9) 2_756 . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.328 _refine_diff_density_min -0.233 _refine_diff_density_rms 0.056 #===============================================END data_2 _database_code_CSD 154921 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-bromo-1,3,2-benzodioxaborole ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H4 B Br O2' _chemical_formula_weight 198.81 _ccdc_compound_id '2' _ccdc_biological_activity '?' _ccdc_polymorph '?' _ccdc_disorder 'none' _ccdc_comments '?' 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' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Br' 'Br' -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' '-x, -y, -z' '-x, y, -z-1/2' '-x+1/2, -y+1/2, -z' '-x+1/2, y+1/2, -z-1/2' _cell_length_a 10.7250(4) _cell_length_b 10.0682(4) _cell_length_c 7.2078(3) _cell_angle_alpha 90.00 _cell_angle_beta 119.53(1) _cell_angle_gamma 90.00 _cell_volume 677.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2574 _cell_measurement_theta_min 5.9 _cell_measurement_theta_max 29.9 _exptl_crystal_description 'ellipsoid' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.57 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.950 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 384 _exptl_absorpt_coefficient_mu 5.992 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.1314 _exptl_absorpt_correction_T_max 0.3049 _exptl_absorpt_process_details 'SADABS (G.M.Sheldrick,1998)' _exptl_special_details ; Five sets of \w scans (each scan 0.3\% in \w), each set at different \f and 2\q angles, nominally covered whole sphere of reciprocal space. Crystal to detector distance 4.51 cm. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'SMART 1K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% 0 _diffrn_reflns_number 3032 _diffrn_reflns_av_R_equivalents 0.0250 _diffrn_reflns_av_sigmaI/netI 0.0163 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.98 _diffrn_reflns_theta_max 29.89 _reflns_number_total 914 _reflns_number_gt 880 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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. ; _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^)+(0.0500P)^2^+0.0800P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 914 _refine_ls_number_parameters 55 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0255 _refine_ls_R_factor_gt 0.0243 _refine_ls_wR_factor_ref 0.0637 _refine_ls_wR_factor_gt 0.0629 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _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 Br1 Br 0.5000 0.40782(2) 0.2500 0.02767(12) Uani 1 2 d S . . O1 O 0.38426(12) 0.14451(13) 0.22262(18) 0.0219(2) Uani 1 1 d . . . B1 B 0.5000 0.2193(3) 0.2500 0.0226(4) Uani 1 2 d S . . C1 C 0.43026(16) 0.01363(17) 0.2339(2) 0.0200(3) Uani 1 1 d . . . C2 C 0.3571(2) -0.10230(16) 0.2179(3) 0.0238(3) Uani 1 1 d . . . C3 C 0.43032(18) -0.22054(18) 0.2352(3) 0.0259(3) Uani 1 1 d . . . H2 H 0.266(3) -0.102(2) 0.195(5) 0.027(7) Uiso 1 1 d . . . H3 H 0.382(3) -0.302(3) 0.226(5) 0.049(8) 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 Br1 0.02871(17) 0.02257(15) 0.03602(17) 0.000 0.01925(12) 0.000 O1 0.0187(5) 0.0242(6) 0.0242(5) -0.0010(4) 0.0117(4) 0.0008(4) B1 0.0215(11) 0.0249(11) 0.0233(10) 0.000 0.0124(9) 0.000 C1 0.0175(7) 0.0253(8) 0.0167(6) -0.0009(5) 0.0081(5) 0.0004(6) C2 0.0204(8) 0.0286(9) 0.0208(7) -0.0021(5) 0.0089(6) -0.0035(5) C3 0.0257(9) 0.0270(8) 0.0219(7) -0.0017(6) 0.0093(6) -0.0052(7) _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 Br1 B1 1.898(3) . ? O1 B1 1.3805(18) . ? O1 C1 1.395(2) . ? C1 C2 1.379(2) . ? C1 C1 1.396(3) 6_656 ? C2 C3 1.398(3) . ? C3 C3 1.402(4) 6_656 ? 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 O1 C1 103.87(14) . . ? O1 B1 O1 113.9(2) . 6_656 ? O1 B1 Br1 123.07(11) . . ? C2 C1 O1 128.60(15) . . ? C2 C1 C1 122.20(10) . 6_656 ? O1 C1 C1 109.20(8) . 6_656 ? C1 C2 C3 116.21(17) . . ? C2 C3 C3 121.59(10) . 6_656 ? _diffrn_measured_fraction_theta_max 0.928 _diffrn_reflns_theta_full 29.89 _diffrn_measured_fraction_theta_full 0.928 _refine_diff_density_max 0.953 _refine_diff_density_min -0.387 _refine_diff_density_rms 0.092 #==============================================END data_3a _database_code_CSD 154922 _audit_creation_method SHELXL _chemical_name_systematic ; 2-chloro-2-(trimethylphosphino)-1,3,2-benzodioxaborole ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H13 B Cl O2 P' _chemical_formula_weight 230.42 _chemical_melting_point ? _chemical_compound_source ? _ccdc_compound_id '3a' _ccdc_biological_activity '?' _ccdc_polymorph '?' _ccdc_disorder 'none' _ccdc_comments '?' 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' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'P' 'P' 0.1023 0.0942 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.2244(10) _cell_length_b 16.3667(14) _cell_length_c 12.7944(11) _cell_angle_alpha 90.00 _cell_angle_beta 117.195(2) _cell_angle_gamma 90.00 _cell_volume 2276.8(3) _cell_formula_units_Z 8 _cell_measurement_temperature 160(2) _cell_measurement_reflns_used 10821 _cell_measurement_theta_min 1.87 _cell_measurement_theta_max 28.40 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.44 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.344 _exptl_crystal_density_method ? _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 0.447 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.775 _exptl_absorpt_correction_T_max 0.898 _exptl_special_details ; Four sets of \w scans, each set at different \f and/or 2\q angles, nominally covered over a hemisphere of reciprocal space. ; _diffrn_ambient_temperature 160(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens SMART CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% 0 _diffrn_reflns_number 14114 _diffrn_reflns_av_R_equivalents 0.0349 _diffrn_reflns_av_sigmaI/netI 0.0258 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 28.52 _reflns_number_total 5258 _reflns_number_observed 4754 _reflns_observed_criterion I>2\s(I) _computing_data_collection 'Siemens SMART' _computing_cell_refinement 'local programs' _computing_data_reduction 'Siemens SAINT' _computing_structure_solution 'SHELXS-96 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-96 (Sheldrick, 1996)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0341P)^2^+1.1991P] 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 SHELXL _refine_ls_extinction_coef 0.0012(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 5258 _refine_ls_number_parameters 260 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0371 _refine_ls_R_factor_obs 0.0317 _refine_ls_wR_factor_all 0.0842 _refine_ls_wR_factor_obs 0.0799 _refine_ls_goodness_of_fit_all 1.110 _refine_ls_goodness_of_fit_obs 1.109 _refine_ls_restrained_S_all 1.110 _refine_ls_restrained_S_obs 1.109 _refine_ls_shift/esd_max 0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.41862(9) 0.12158(6) 0.05064(9) 0.0210(2) Uani 1 d . . B1 B 0.34434(15) 0.18522(10) 0.06666(14) 0.0193(3) Uani 1 d . . O2 O 0.34126(9) 0.16941(6) 0.17741(9) 0.0207(2) Uani 1 d . . C1 C 0.47208(12) 0.08036(8) 0.15542(12) 0.0189(3) Uani 1 d . . C2 C 0.42633(12) 0.10876(9) 0.23041(12) 0.0189(3) Uani 1 d . . C3 C 0.46623(14) 0.07780(9) 0.34181(13) 0.0240(3) Uani 1 d . . H3 H 0.4354 0.0976 0.3931 0.029 Uiso 1 calc R . C4 C 0.55491(15) 0.01545(10) 0.37601(14) 0.0299(3) Uani 1 d . . H4 H 0.5844 -0.0079 0.4521 0.036 Uiso 1 calc R . C5 C 0.60007(14) -0.01257(10) 0.30153(15) 0.0305(4) Uani 1 d . . H5 H 0.6601 -0.0547 0.3276 0.037 Uiso 1 calc R . C6 C 0.55951(14) 0.01965(9) 0.18828(14) 0.0255(3) Uani 1 d . . H6 H 0.5907 0.0006 0.1370 0.031 Uiso 1 calc R . Cl1 Cl 0.40795(4) 0.29181(2) 0.06642(3) 0.02616(10) Uani 1 d . . P1 P 0.17894(3) 0.18554(2) -0.06737(3) 0.01914(9) Uani 1 d . . C7 C 0.10143(16) 0.09128(10) -0.07133(14) 0.0304(3) Uani 1 d . . H7A H 0.1542 0.0451 -0.0676 0.046 Uiso 1 calc R . H7B H 0.0243 0.0884 -0.1444 0.046 Uiso 1 calc R . H7C H 0.0836 0.0890 -0.0041 0.046 Uiso 1 calc R . C8 C 0.08546(15) 0.26713(10) -0.05914(14) 0.0287(3) Uani 1 d . . H8A H 0.0753 0.2610 0.0121 0.043 Uiso 1 calc R . H8B H 0.0047 0.2655 -0.1283 0.043 Uiso 1 calc R . H8C H 0.1253 0.3196 -0.0567 0.043 Uiso 1 calc R . C9 C 0.18995(16) 0.19344(11) -0.20263(14) 0.0301(4) Uani 1 d . . H9A H 0.2335 0.2438 -0.2021 0.045 Uiso 1 calc R . H9B H 0.1072 0.1945 -0.2690 0.045 Uiso 1 calc R . H9C H 0.2351 0.1463 -0.2103 0.045 Uiso 1 calc R . B2 B 0.16877(15) 0.69282(10) 0.42532(14) 0.0193(3) Uani 1 d . . O3 O 0.04670(9) 0.66813(7) 0.40832(9) 0.0220(2) Uani 1 d . . O4 O 0.20499(9) 0.63581(6) 0.35939(9) 0.0208(2) Uani 1 d . . C11 C 0.00580(13) 0.61324(9) 0.31719(12) 0.0193(3) Uani 1 d . . C12 C 0.09955(13) 0.59474(8) 0.28738(12) 0.0186(3) Uani 1 d . . C13 C 0.08136(14) 0.54184(9) 0.19720(13) 0.0237(3) Uani 1 d . . H13 H 0.1451 0.5300 0.1765 0.028 Uiso 1 calc R . C14 C -0.03556(16) 0.50616(10) 0.13722(14) 0.0285(3) Uani 1 d . . H14 H -0.0517 0.4693 0.0744 0.034 Uiso 1 calc R . C15 C -0.12795(15) 0.52377(10) 0.16813(14) 0.0288(3) Uani 1 d . . H15 H -0.2058 0.4981 0.1267 0.035 Uiso 1 calc R . C16 C -0.10931(14) 0.57854(10) 0.25903(13) 0.0247(3) Uani 1 d . . H16 H -0.1729 0.5911 0.2795 0.030 Uiso 1 calc R . Cl2 Cl 0.16405(4) 0.80243(2) 0.37044(3) 0.02915(10) Uani 1 d . . P2 P 0.29380(3) 0.69546(2) 0.59120(3) 0.01798(9) Uani 1 d . . C17 C 0.28369(15) 0.60551(10) 0.66714(15) 0.0293(3) Uani 1 d . . H17A H 0.3450 0.6086 0.7499 0.044 Uiso 1 calc R . H17B H 0.2993 0.5570 0.6311 0.044 Uiso 1 calc R . H17C H 0.2013 0.6019 0.6618 0.044 Uiso 1 calc R . C18 C 0.28049(15) 0.78312(10) 0.66868(14) 0.0266(3) Uani 1 d . . H18A H 0.3390 0.7783 0.7522 0.040 Uiso 1 calc R . H18B H 0.1967 0.7863 0.6599 0.040 Uiso 1 calc R . H18C H 0.2985 0.8326 0.6363 0.040 Uiso 1 calc R . C19 C 0.44347(14) 0.69771(10) 0.59783(15) 0.0276(3) Uani 1 d . . H19A H 0.4516 0.7471 0.5586 0.041 Uiso 1 calc R . H19B H 0.4542 0.6493 0.5584 0.041 Uiso 1 calc R . H19C H 0.5064 0.6980 0.6802 0.041 Uiso 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 O1 0.0227(5) 0.0231(5) 0.0193(5) 0.0033(4) 0.0113(4) 0.0053(4) B1 0.0194(7) 0.0193(7) 0.0187(7) 0.0010(6) 0.0083(6) 0.0015(6) O2 0.0216(5) 0.0230(5) 0.0194(5) 0.0025(4) 0.0109(4) 0.0042(4) C1 0.0173(6) 0.0180(6) 0.0211(7) 0.0016(5) 0.0085(5) -0.0032(5) C2 0.0162(6) 0.0180(6) 0.0209(7) 0.0008(5) 0.0071(5) -0.0031(5) C3 0.0249(7) 0.0259(7) 0.0206(7) 0.0020(6) 0.0098(6) -0.0049(6) C4 0.0276(8) 0.0294(8) 0.0258(8) 0.0118(6) 0.0063(6) -0.0018(7) C5 0.0217(7) 0.0243(8) 0.0409(9) 0.0114(7) 0.0104(7) 0.0037(6) C6 0.0219(7) 0.0213(7) 0.0361(8) 0.0023(6) 0.0155(6) 0.0013(6) Cl1 0.02961(19) 0.02132(18) 0.02787(19) -0.00037(13) 0.01342(15) -0.00494(14) P1 0.01800(18) 0.02194(19) 0.01700(18) 0.00126(13) 0.00758(14) 0.00145(14) C7 0.0337(8) 0.0299(8) 0.0286(8) -0.0075(6) 0.0152(7) -0.0102(7) C8 0.0274(8) 0.0312(8) 0.0309(8) 0.0076(7) 0.0161(7) 0.0099(7) C9 0.0275(8) 0.0451(10) 0.0200(7) 0.0027(7) 0.0130(6) 0.0034(7) B2 0.0191(7) 0.0200(7) 0.0187(7) -0.0003(6) 0.0085(6) 0.0007(6) O3 0.0189(5) 0.0260(5) 0.0228(5) -0.0051(4) 0.0108(4) -0.0007(4) O4 0.0189(5) 0.0231(5) 0.0224(5) -0.0040(4) 0.0111(4) -0.0018(4) C11 0.0213(7) 0.0187(7) 0.0180(6) 0.0013(5) 0.0089(5) 0.0003(5) C12 0.0201(6) 0.0173(6) 0.0185(6) 0.0028(5) 0.0089(5) 0.0008(5) C13 0.0295(8) 0.0211(7) 0.0225(7) -0.0001(6) 0.0136(6) 0.0011(6) C14 0.0363(9) 0.0234(7) 0.0219(7) -0.0039(6) 0.0099(7) -0.0038(6) C15 0.0259(8) 0.0266(8) 0.0261(8) 0.0007(6) 0.0052(6) -0.0067(6) C16 0.0205(7) 0.0272(8) 0.0250(7) 0.0032(6) 0.0092(6) -0.0012(6) Cl2 0.0350(2) 0.02082(18) 0.0281(2) 0.00406(14) 0.01132(16) 0.00133(14) P2 0.01602(17) 0.02003(18) 0.01888(18) -0.00185(13) 0.00883(14) -0.00064(13) C17 0.0289(8) 0.0278(8) 0.0329(8) 0.0079(7) 0.0156(7) 0.0016(6) C18 0.0246(7) 0.0297(8) 0.0290(8) -0.0105(6) 0.0153(6) -0.0031(6) C19 0.0193(7) 0.0377(9) 0.0297(8) -0.0033(7) 0.0145(6) -0.0008(6) _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 O1 C1 1.3706(17) . ? O1 B1 1.4565(18) . ? B1 O2 1.4578(18) . ? B1 Cl1 1.9105(17) . ? B1 P1 1.9646(17) . ? O2 C2 1.3719(17) . ? C1 C6 1.3768(20) . ? C1 C2 1.3928(20) . ? C2 C3 1.3751(20) . ? C3 C4 1.4051(23) . ? C4 C5 1.3799(25) . ? C5 C6 1.4024(23) . ? P1 C8 1.7917(16) . ? P1 C7 1.7991(16) . ? P1 C9 1.8007(16) . ? B2 O4 1.4559(18) . ? B2 O3 1.4631(19) . ? B2 Cl2 1.9178(17) . ? B2 P2 1.9691(17) . ? O3 C11 1.3725(17) . ? O4 C12 1.3699(17) . ? C11 C16 1.3782(20) . ? C11 C12 1.3964(20) . ? C12 C13 1.3770(20) . ? C13 C14 1.4037(22) . ? C14 C15 1.3867(24) . ? C15 C16 1.4020(23) . ? P2 C19 1.7928(16) . ? P2 C18 1.7931(15) . ? P2 C17 1.7990(16) . ? 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 C1 O1 B1 105.28(11) . . ? O1 B1 O2 107.74(11) . . ? O1 B1 Cl1 111.86(10) . . ? O2 B1 Cl1 110.79(10) . . ? O1 B1 P1 109.77(10) . . ? O2 B1 P1 112.05(10) . . ? Cl1 B1 P1 104.68(8) . . ? C2 O2 B1 104.97(11) . . ? O1 C1 C6 127.62(14) . . ? O1 C1 C2 110.33(12) . . ? C6 C1 C2 122.04(14) . . ? O2 C2 C3 127.49(13) . . ? O2 C2 C1 110.69(12) . . ? C3 C2 C1 121.82(14) . . ? C2 C3 C4 116.62(14) . . ? C5 C4 C3 121.43(14) . . ? C4 C5 C6 121.64(15) . . ? C1 C6 C5 116.45(15) . . ? C8 P1 C7 107.40(8) . . ? C8 P1 C9 109.44(8) . . ? C7 P1 C9 107.71(8) . . ? C8 P1 B1 112.35(7) . . ? C7 P1 B1 109.93(8) . . ? C9 P1 B1 109.87(7) . . ? O4 B2 O3 107.25(12) . . ? O4 B2 Cl2 110.71(10) . . ? O3 B2 Cl2 110.24(10) . . ? O4 B2 P2 110.29(10) . . ? O3 B2 P2 113.75(10) . . ? Cl2 B2 P2 104.64(8) . . ? C11 O3 B2 104.94(11) . . ? C12 O4 B2 105.21(11) . . ? O3 C11 C16 127.88(13) . . ? O3 C11 C12 110.37(12) . . ? C16 C11 C12 121.74(14) . . ? O4 C12 C13 127.88(13) . . ? O4 C12 C11 110.33(12) . . ? C13 C12 C11 121.79(14) . . ? C12 C13 C14 116.99(14) . . ? C15 C14 C13 121.08(14) . . ? C14 C15 C16 121.64(15) . . ? C11 C16 C15 116.75(14) . . ? C19 P2 C18 107.81(8) . . ? C19 P2 C17 108.17(8) . . ? C18 P2 C17 108.07(8) . . ? C19 P2 B2 108.91(7) . . ? C18 P2 B2 113.05(7) . . ? C17 P2 B2 110.68(7) . . ? _refine_diff_density_max 0.407 _refine_diff_density_min -0.360 _refine_diff_density_rms 0.051 #==========================================END data_3b _database_code_CSD 154923 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-chloro-2-(triethylphosphino)-1,3,2-benzodioxaborole ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H19 B Cl O2 P' _chemical_formula_weight 272.50 _ccdc_compound_id '3b' _ccdc_biological_activity '?' _ccdc_polymorph '?' _ccdc_disorder 'none' _ccdc_comments '?' 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' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'P' 'P' 0.1023 0.0942 '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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 13.4416(12) _cell_length_b 14.0419(12) _cell_length_c 14.6040(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2756.4(4) _cell_formula_units_Z 8 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 926 _cell_measurement_theta_min 13.61 _cell_measurement_theta_max 23.63 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.313 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1152 _exptl_absorpt_coefficient_mu 0.380 _exptl_absorpt_correction_type 'none' _exptl_absorpt_correction_T_min . _exptl_absorpt_correction_T_max . _exptl_absorpt_process_details . _exptl_special_details ; Four sets of \w scans (each scan 0.3\% in \w), each set at different \f and/or 2\q angles, nominally covered over a hemisphere of reciprocal space. The first 50 scans were repeated at the end of data collection, revealing no significant crystal decay. Crystal to detector distance 4.51 cm. ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'SMART 1K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% 0 _diffrn_reflns_number 27702 _diffrn_reflns_av_R_equivalents 0.1318 _diffrn_reflns_av_sigmaI/netI 0.0491 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.52 _diffrn_reflns_theta_max 27.52 _reflns_number_total 3169 _reflns_number_gt 2756 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _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. ; _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^)+(0.0492P)^2^+1.1681P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3169 _refine_ls_number_parameters 230 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0462 _refine_ls_R_factor_gt 0.0393 _refine_ls_wR_factor_ref 0.1059 _refine_ls_wR_factor_gt 0.0993 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _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 B1 B 0.64592(13) -0.12842(12) 0.66502(12) 0.0229(3) Uani 1 1 d . . . Cl1 Cl 0.56932(3) -0.22283(3) 0.72961(3) 0.03196(14) Uani 1 1 d . . . C1 C 0.71639(11) -0.17019(10) 0.53065(11) 0.0223(3) Uani 1 1 d . . . O1 O 0.62792(8) -0.13711(8) 0.56682(8) 0.0241(2) Uani 1 1 d . . . C2 C 0.79018(12) -0.17126(10) 0.59770(11) 0.0230(3) Uani 1 1 d . . . O2 O 0.75248(8) -0.14199(8) 0.68078(8) 0.0263(3) Uani 1 1 d . . . C3 C 0.88684(12) -0.19888(12) 0.57765(13) 0.0292(4) Uani 1 1 d . . . H3 H 0.9358(17) -0.2004(15) 0.6236(16) 0.038(6) Uiso 1 1 d . . . C4 C 0.90636(14) -0.22808(12) 0.48737(14) 0.0339(4) Uani 1 1 d . . . H4 H 0.9705(18) -0.2473(16) 0.4715(16) 0.041(6) Uiso 1 1 d . . . C5 C 0.83194(15) -0.22948(12) 0.42122(13) 0.0334(4) Uani 1 1 d . . . H5 H 0.8430(17) -0.2502(16) 0.3601(17) 0.043(6) Uiso 1 1 d . . . C6 C 0.73427(14) -0.19999(12) 0.44208(12) 0.0282(3) Uani 1 1 d . . . H6 H 0.6844(16) -0.1991(15) 0.3947(16) 0.038(6) Uiso 1 1 d . . . P1 P 0.59972(3) -0.00031(3) 0.70886(3) 0.02225(13) Uani 1 1 d . . . C10 C 0.54797(14) 0.00195(12) 0.82408(12) 0.0295(4) Uani 1 1 d . . . H10A H 0.4902(17) -0.0357(15) 0.8212(16) 0.036(5) Uiso 1 1 d . . . H10B H 0.5280(19) 0.0696(18) 0.8356(18) 0.052(7) Uiso 1 1 d . . . C11 C 0.61810(16) -0.03370(16) 0.89888(13) 0.0380(4) Uani 1 1 d . . . H11A H 0.647(2) -0.099(2) 0.886(2) 0.066(8) Uiso 1 1 d . . . H11B H 0.674(2) 0.011(2) 0.907(2) 0.066(8) Uiso 1 1 d . . . H11C H 0.583(2) -0.040(2) 0.960(2) 0.062(8) Uiso 1 1 d . . . C20 C 0.50233(13) 0.04492(12) 0.63382(12) 0.0289(3) Uani 1 1 d . . . H20A H 0.5320(17) 0.0566(17) 0.5769(18) 0.045(6) Uiso 1 1 d . . . H20B H 0.4809(18) 0.1072(17) 0.6590(18) 0.048(7) Uiso 1 1 d . . . C21 C 0.41345(14) -0.02246(15) 0.62506(15) 0.0347(4) Uani 1 1 d . . . H21A H 0.3641(19) 0.0054(16) 0.5843(18) 0.045(7) Uiso 1 1 d . . . H21B H 0.3822(19) -0.0350(19) 0.684(2) 0.054(7) Uiso 1 1 d . . . H21C H 0.4325(18) -0.0846(18) 0.5991(17) 0.046(6) Uiso 1 1 d . . . C30 C 0.70228(14) 0.08470(12) 0.70457(12) 0.0294(4) Uani 1 1 d . . . H30A H 0.7472(19) 0.0681(18) 0.7530(18) 0.049(6) Uiso 1 1 d . . . H30B H 0.6737(17) 0.1489(17) 0.7183(16) 0.043(6) Uiso 1 1 d . . . C31 C 0.75792(14) 0.08536(13) 0.61317(14) 0.0337(4) Uani 1 1 d . . . H31A H 0.715(2) 0.1061(18) 0.5619(19) 0.055(7) Uiso 1 1 d . . . H31B H 0.7853(19) 0.0242(18) 0.5990(18) 0.049(7) Uiso 1 1 d . . . H31C H 0.8120(17) 0.1290(16) 0.6153(16) 0.040(6) 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 B1 0.0241(8) 0.0222(8) 0.0226(8) -0.0007(6) 0.0000(6) 0.0016(6) Cl1 0.0407(3) 0.0247(2) 0.0305(2) 0.00229(15) 0.00680(17) -0.00293(15) C1 0.0251(7) 0.0172(7) 0.0247(7) 0.0009(5) 0.0011(6) 0.0006(5) O1 0.0223(5) 0.0278(6) 0.0222(5) -0.0012(4) -0.0012(4) 0.0036(4) C2 0.0259(7) 0.0173(7) 0.0256(7) -0.0006(6) -0.0009(6) 0.0006(5) O2 0.0258(6) 0.0296(6) 0.0237(6) -0.0035(4) -0.0035(4) 0.0038(4) C3 0.0243(8) 0.0228(8) 0.0403(10) -0.0002(7) -0.0022(7) 0.0015(6) C4 0.0306(9) 0.0272(9) 0.0440(11) 0.0016(7) 0.0099(8) 0.0069(6) C5 0.0467(10) 0.0257(8) 0.0278(8) 0.0001(7) 0.0095(7) 0.0079(7) C6 0.0377(9) 0.0233(8) 0.0236(8) 0.0007(6) -0.0009(7) 0.0035(6) P1 0.0252(2) 0.0204(2) 0.0212(2) -0.00091(14) -0.00018(15) 0.00137(14) C10 0.0337(9) 0.0299(9) 0.0247(8) -0.0021(6) 0.0045(7) 0.0013(7) C11 0.0443(11) 0.0453(11) 0.0243(9) 0.0031(8) -0.0033(8) -0.0009(9) C20 0.0337(9) 0.0243(8) 0.0288(8) 0.0003(6) -0.0061(7) 0.0044(6) C21 0.0276(9) 0.0386(10) 0.0380(10) -0.0011(8) -0.0053(8) 0.0023(7) C30 0.0337(9) 0.0249(8) 0.0295(9) -0.0025(6) -0.0011(7) -0.0042(7) C31 0.0350(9) 0.0275(9) 0.0385(10) 0.0005(7) 0.0073(8) -0.0034(7) _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 B1 O1 1.459(2) . ? B1 O2 1.463(2) . ? B1 Cl1 1.9254(18) . ? B1 P1 2.0079(18) . ? C1 C6 1.381(2) . ? C1 O1 1.3817(18) . ? C1 C2 1.394(2) . ? C2 O2 1.3776(19) . ? C2 C3 1.387(2) . ? C3 C4 1.405(3) . ? C4 C5 1.391(3) . ? C5 C6 1.410(3) . ? P1 C10 1.8210(18) . ? P1 C20 1.8215(17) . ? P1 C30 1.8247(18) . ? C10 C11 1.527(3) . ? C20 C21 1.529(3) . ? C30 C31 1.530(3) . ? 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 O2 107.82(13) . . ? O1 B1 Cl1 109.58(11) . . ? O2 B1 Cl1 110.90(11) . . ? O1 B1 P1 109.69(11) . . ? O2 B1 P1 111.67(11) . . ? Cl1 B1 P1 107.17(8) . . ? C6 C1 O1 127.58(15) . . ? C6 C1 C2 122.08(15) . . ? O1 C1 C2 110.34(13) . . ? C1 O1 B1 105.13(12) . . ? O2 C2 C3 127.87(15) . . ? O2 C2 C1 110.71(13) . . ? C3 C2 C1 121.41(15) . . ? C2 O2 B1 105.10(12) . . ? C2 C3 C4 117.03(16) . . ? C5 C4 C3 121.43(16) . . ? C4 C5 C6 121.03(17) . . ? C1 C6 C5 116.97(16) . . ? C10 P1 C20 105.98(9) . . ? C10 P1 C30 107.99(8) . . ? C20 P1 C30 107.11(8) . . ? C10 P1 B1 115.37(8) . . ? C20 P1 B1 110.05(8) . . ? C30 P1 B1 109.97(8) . . ? C11 C10 P1 114.80(13) . . ? C21 C20 P1 113.33(12) . . ? C31 C30 P1 113.78(12) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.559 _refine_diff_density_min -0.454 _refine_diff_density_rms 0.067 #===================================================END data_3d _database_code_CSD 154924 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-chloro-2-{tris-(tert-butyl)phosphino}-1,3,2-benzodioxaborole ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H31 B Cl O2 P' _chemical_formula_weight 356.66 _ccdc_compound_id '3d' _ccdc_biological_activity '?' _ccdc_polymorph '?' _ccdc_disorder 'none' _ccdc_comments '?' 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' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'P' 'P' 0.1023 0.0942 '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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pna2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 16.664(1) _cell_length_b 13.455(5) _cell_length_c 8.546(1) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1916.1(8) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 948 _cell_measurement_theta_min 12.0 _cell_measurement_theta_max 25.4 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.236 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.289 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8412 _exptl_absorpt_correction_T_max 0.9281 _exptl_absorpt_process_details 'SADABS (G.M.Sheldrick, 1998) program; R(int)=0.040 before correction' _exptl_special_details ; Four sets of \w scans (each scan 0.3\% in \w, exposure time 10 s), each set at different \f and/or 2\q angles, nominally covered over a hemisphere of reciprocal space. The first 50 scans were repeated at the end of data collection, revealing no significant crystal decay. Crystal to detector distance 4.51 cm. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'SMART 1K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% 0 _diffrn_reflns_number 14595 _diffrn_reflns_av_R_equivalents 0.0242 _diffrn_reflns_av_sigmaI/netI 0.0275 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 29.12 _reflns_number_total 4985 _reflns_number_gt 4570 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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. ; _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^)+(0.0391P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.04(4) _refine_ls_number_reflns 4985 _refine_ls_number_parameters 332 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0306 _refine_ls_R_factor_gt 0.0257 _refine_ls_wR_factor_ref 0.0598 _refine_ls_wR_factor_gt 0.0580 _refine_ls_goodness_of_fit_ref 0.998 _refine_ls_restrained_S_all 0.998 _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 P1 P 0.203568(17) 0.33192(2) 0.48357(4) 0.01387(7) Uani 1 1 d . . . Cl1 Cl 0.356031(17) 0.19396(2) 0.57328(4) 0.02246(7) Uani 1 1 d . . . B1 B 0.31664(8) 0.28684(11) 0.42200(19) 0.0171(3) Uani 1 1 d . . . O1 O 0.31721(6) 0.24041(7) 0.26767(12) 0.02018(19) Uani 1 1 d . . . O2 O 0.37147(5) 0.37234(7) 0.41498(11) 0.01818(18) Uani 1 1 d . . . C1 C 0.37810(8) 0.28581(10) 0.18656(16) 0.0195(3) Uani 1 1 d . . . C2 C 0.41024(8) 0.36412(10) 0.27393(15) 0.0174(2) Uani 1 1 d . . . C3 C 0.47162(8) 0.42294(10) 0.21655(17) 0.0206(3) Uani 1 1 d . . . H3 H 0.4923(9) 0.4753(12) 0.2762(18) 0.017(4) Uiso 1 1 d . . . C4 C 0.49951(8) 0.40170(11) 0.06542(19) 0.0254(3) Uani 1 1 d . . . H4 H 0.5401(11) 0.4403(14) 0.025(2) 0.038(5) Uiso 1 1 d . . . C5 C 0.46688(8) 0.32531(12) -0.0220(2) 0.0275(3) Uani 1 1 d . . . H5 H 0.4877(12) 0.3149(13) -0.117(3) 0.035(5) Uiso 1 1 d . . . C6 C 0.40492(8) 0.26527(11) 0.03730(17) 0.0238(3) Uani 1 1 d . . . H6 H 0.3833(10) 0.2179(13) -0.024(2) 0.026(4) Uiso 1 1 d . . . C10 C 0.15491(8) 0.38440(10) 0.29910(15) 0.0186(3) Uani 1 1 d . . . C11 C 0.08103(9) 0.45055(12) 0.3326(2) 0.0260(3) Uani 1 1 d . . . H111 H 0.0592(10) 0.4701(13) 0.238(2) 0.031(5) Uiso 1 1 d . . . H112 H 0.0388(11) 0.4174(14) 0.383(2) 0.030(5) Uiso 1 1 d . . . H113 H 0.0943(13) 0.5106(16) 0.391(2) 0.048(6) Uiso 1 1 d . . . C12 C 0.21694(9) 0.44577(11) 0.20708(18) 0.0224(3) Uani 1 1 d . . . H121 H 0.1895(10) 0.4780(13) 0.121(2) 0.025(4) Uiso 1 1 d . . . H122 H 0.2421(10) 0.4972(13) 0.267(2) 0.027(4) Uiso 1 1 d . . . H123 H 0.2555(10) 0.4027(15) 0.168(2) 0.029(4) Uiso 1 1 d . . . C13 C 0.12844(9) 0.29978(12) 0.18798(17) 0.0238(3) Uani 1 1 d . . . H131 H 0.1710(10) 0.2533(13) 0.162(2) 0.023(4) Uiso 1 1 d . . . H132 H 0.0823(12) 0.2632(14) 0.232(3) 0.038(5) Uiso 1 1 d . . . H133 H 0.1133(11) 0.3330(13) 0.098(3) 0.033(5) Uiso 1 1 d . . . C20 C 0.14246(7) 0.22316(9) 0.56136(17) 0.0170(2) Uani 1 1 d . . . C21 C 0.16082(8) 0.13064(10) 0.46046(17) 0.0200(3) Uani 1 1 d . . . H211 H 0.1305(9) 0.0733(13) 0.504(2) 0.026(4) Uiso 1 1 d . . . H212 H 0.1452(9) 0.1383(13) 0.354(2) 0.019(4) Uiso 1 1 d . . . H213 H 0.2177(10) 0.1109(13) 0.463(2) 0.028(4) Uiso 1 1 d . . . C22 C 0.05143(7) 0.24321(11) 0.55709(18) 0.0215(3) Uani 1 1 d . . . H221 H 0.0333(10) 0.2993(13) 0.618(2) 0.024(4) Uiso 1 1 d . . . H222 H 0.0339(10) 0.2560(13) 0.452(2) 0.029(5) Uiso 1 1 d . . . H223 H 0.0243(11) 0.1893(14) 0.594(2) 0.036(5) Uiso 1 1 d . . . C23 C 0.16463(8) 0.19646(11) 0.73142(17) 0.0208(3) Uani 1 1 d . . . H231 H 0.1388(9) 0.1347(13) 0.758(2) 0.022(4) Uiso 1 1 d . . . H232 H 0.2216(11) 0.1804(13) 0.746(2) 0.033(5) Uiso 1 1 d . . . H233 H 0.1491(8) 0.2466(12) 0.8083(19) 0.014(4) Uiso 1 1 d . . . C30 C 0.21412(8) 0.43293(10) 0.63758(16) 0.0195(3) Uani 1 1 d . . . C31 C 0.24582(9) 0.53008(10) 0.5644(2) 0.0244(3) Uani 1 1 d . . . H311 H 0.2959(10) 0.5212(13) 0.515(2) 0.024(4) Uiso 1 1 d . . . H312 H 0.2091(10) 0.5623(12) 0.490(2) 0.026(4) Uiso 1 1 d . . . H313 H 0.2552(9) 0.5765(13) 0.657(2) 0.024(4) Uiso 1 1 d . . . C32 C 0.13466(9) 0.45691(12) 0.72272(18) 0.0267(3) Uani 1 1 d . . . H321 H 0.1462(11) 0.5176(16) 0.790(3) 0.042(5) Uiso 1 1 d . . . H322 H 0.0934(10) 0.4771(12) 0.651(2) 0.020(4) Uiso 1 1 d . . . H323 H 0.1160(11) 0.4026(14) 0.785(2) 0.030(4) Uiso 1 1 d . . . C33 C 0.27751(9) 0.39972(12) 0.75893(18) 0.0246(3) Uani 1 1 d . . . H331 H 0.2642(11) 0.3432(15) 0.810(2) 0.029(4) Uiso 1 1 d . . . H332 H 0.3315(11) 0.3931(13) 0.713(2) 0.032(5) Uiso 1 1 d . . . H333 H 0.2826(10) 0.4504(14) 0.841(2) 0.030(4) 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 P1 0.01350(13) 0.01471(13) 0.01340(13) -0.00096(13) 0.00028(12) 0.00022(11) Cl1 0.01539(13) 0.02244(14) 0.02956(16) 0.00729(14) 0.00030(13) 0.00102(11) B1 0.0155(6) 0.0173(7) 0.0185(6) 0.0009(6) 0.0009(5) -0.0008(5) O1 0.0198(4) 0.0193(5) 0.0215(5) -0.0037(4) 0.0050(4) -0.0031(4) O2 0.0166(4) 0.0196(5) 0.0183(4) -0.0012(4) 0.0034(4) -0.0030(3) C1 0.0162(6) 0.0203(6) 0.0221(7) 0.0014(5) 0.0014(5) 0.0018(5) C2 0.0157(6) 0.0185(6) 0.0180(6) 0.0028(5) 0.0009(5) 0.0021(5) C3 0.0171(6) 0.0212(6) 0.0233(6) 0.0052(6) -0.0006(5) 0.0001(5) C4 0.0183(6) 0.0314(7) 0.0264(7) 0.0099(7) 0.0045(6) 0.0003(5) C5 0.0234(6) 0.0403(8) 0.0188(6) 0.0044(7) 0.0066(7) 0.0054(6) C6 0.0212(6) 0.0275(7) 0.0226(7) -0.0041(5) 0.0023(5) 0.0018(5) C10 0.0190(6) 0.0207(6) 0.0162(6) 0.0012(5) -0.0020(5) 0.0018(5) C11 0.0220(7) 0.0282(8) 0.0278(8) 0.0031(6) -0.0031(6) 0.0072(6) C12 0.0258(7) 0.0210(7) 0.0203(6) 0.0041(6) 0.0002(6) 0.0003(6) C13 0.0263(7) 0.0270(7) 0.0180(7) -0.0011(6) -0.0043(5) -0.0041(6) C20 0.0147(5) 0.0177(5) 0.0187(6) 0.0002(5) 0.0027(5) -0.0013(4) C21 0.0193(6) 0.0188(6) 0.0220(8) -0.0011(5) 0.0027(5) -0.0030(5) C22 0.0141(5) 0.0267(7) 0.0238(7) 0.0001(6) 0.0024(5) -0.0014(5) C23 0.0198(6) 0.0236(7) 0.0192(7) 0.0022(6) 0.0032(5) -0.0011(5) C30 0.0217(6) 0.0176(6) 0.0191(6) -0.0054(5) -0.0004(5) 0.0019(5) C31 0.0286(7) 0.0168(6) 0.0276(7) -0.0047(6) -0.0004(7) -0.0003(5) C32 0.0291(7) 0.0270(8) 0.0240(7) -0.0074(6) 0.0051(6) 0.0041(6) C33 0.0285(7) 0.0241(7) 0.0212(7) -0.0041(6) -0.0057(6) -0.0019(6) _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 P1 C30 1.9001(14) . ? P1 C20 1.9027(13) . ? P1 C10 1.9083(13) . ? P1 B1 2.0482(15) . ? Cl1 B1 1.9141(16) . ? B1 O1 1.4594(18) . ? B1 O2 1.4704(17) . ? O1 C1 1.3723(16) . ? O2 C2 1.3721(16) . ? C1 C6 1.3796(19) . ? C1 C2 1.3980(19) . ? C2 C3 1.3831(18) . ? C3 C4 1.402(2) . ? C3 H3 0.936(16) . ? C4 C5 1.382(2) . ? C4 H4 0.920(19) . ? C5 C6 1.405(2) . ? C5 H5 0.89(2) . ? C6 H6 0.900(19) . ? C10 C12 1.5390(19) . ? C10 C11 1.5459(19) . ? C10 C13 1.5468(19) . ? C11 H111 0.93(2) . ? C11 H112 0.939(19) . ? C11 H113 0.97(2) . ? C12 H121 0.972(18) . ? C12 H122 0.956(18) . ? C12 H123 0.928(19) . ? C13 H131 0.971(18) . ? C13 H132 0.99(2) . ? C13 H133 0.92(2) . ? C20 C22 1.5412(17) . ? C20 C23 1.542(2) . ? C20 C21 1.5449(19) . ? C21 H211 0.994(18) . ? C21 H212 0.949(17) . ? C21 H213 0.985(17) . ? C22 H221 0.964(17) . ? C22 H222 0.96(2) . ? C22 H223 0.910(19) . ? C23 H231 0.962(18) . ? C23 H232 0.982(18) . ? C23 H233 0.976(16) . ? C30 C31 1.543(2) . ? C30 C32 1.5449(19) . ? C30 C33 1.546(2) . ? C31 H311 0.942(17) . ? C31 H312 0.981(18) . ? C31 H313 1.020(18) . ? C32 H321 1.02(2) . ? C32 H322 0.959(18) . ? C32 H323 0.95(2) . ? C33 H331 0.90(2) . ? C33 H332 0.986(19) . ? C33 H333 0.98(2) . ? 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 C30 P1 C20 110.95(6) . . ? C30 P1 C10 110.30(6) . . ? C20 P1 C10 110.23(6) . . ? C30 P1 B1 107.74(6) . . ? C20 P1 B1 110.75(6) . . ? C10 P1 B1 106.75(6) . . ? O1 B1 O2 107.10(11) . . ? O1 B1 Cl1 109.19(9) . . ? O2 B1 Cl1 108.98(9) . . ? O1 B1 P1 111.40(9) . . ? O2 B1 P1 110.51(9) . . ? Cl1 B1 P1 109.59(7) . . ? C1 O1 B1 105.71(10) . . ? C2 O2 B1 105.39(10) . . ? O1 C1 C6 128.13(13) . . ? O1 C1 C2 110.42(12) . . ? C6 C1 C2 121.38(12) . . ? O2 C2 C3 127.84(12) . . ? O2 C2 C1 110.46(11) . . ? C3 C2 C1 121.68(12) . . ? C2 C3 C4 117.07(13) . . ? C2 C3 H3 120.7(10) . . ? C4 C3 H3 122.2(10) . . ? C5 C4 C3 121.27(13) . . ? C5 C4 H4 120.3(12) . . ? C3 C4 H4 118.4(12) . . ? C4 C5 C6 121.45(15) . . ? C4 C5 H5 117.1(12) . . ? C6 C5 H5 121.5(12) . . ? C1 C6 C5 117.14(14) . . ? C1 C6 H6 123.3(12) . . ? C5 C6 H6 119.5(12) . . ? C12 C10 C11 108.70(12) . . ? C12 C10 C13 105.83(11) . . ? C11 C10 C13 108.08(12) . . ? C12 C10 P1 109.59(9) . . ? C11 C10 P1 113.49(10) . . ? C13 C10 P1 110.85(9) . . ? C10 C11 H111 108.3(11) . . ? C10 C11 H112 114.2(11) . . ? H111 C11 H112 104.1(15) . . ? C10 C11 H113 113.0(13) . . ? H111 C11 H113 107.5(17) . . ? H112 C11 H113 109.2(17) . . ? C10 C12 H121 108.2(10) . . ? C10 C12 H122 114.3(10) . . ? H121 C12 H122 106.7(15) . . ? C10 C12 H123 108.3(11) . . ? H121 C12 H123 109.3(16) . . ? H122 C12 H123 109.9(15) . . ? C10 C13 H131 114.1(10) . . ? C10 C13 H132 110.9(12) . . ? H131 C13 H132 109.5(15) . . ? C10 C13 H133 103.4(11) . . ? H131 C13 H133 108.7(15) . . ? H132 C13 H133 110.1(17) . . ? C22 C20 C23 107.39(11) . . ? C22 C20 C21 108.83(11) . . ? C23 C20 C21 106.91(11) . . ? C22 C20 P1 112.58(9) . . ? C23 C20 P1 112.35(9) . . ? C21 C20 P1 108.58(9) . . ? C20 C21 H211 108.5(10) . . ? C20 C21 H212 113.1(11) . . ? H211 C21 H212 107.5(14) . . ? C20 C21 H213 113.4(11) . . ? H211 C21 H213 105.8(14) . . ? H212 C21 H213 108.2(14) . . ? C20 C22 H221 115.6(10) . . ? C20 C22 H222 110.7(10) . . ? H221 C22 H222 105.5(15) . . ? C20 C22 H223 110.0(11) . . ? H221 C22 H223 106.5(16) . . ? H222 C22 H223 108.2(16) . . ? C20 C23 H231 108.4(11) . . ? C20 C23 H232 114.0(12) . . ? H231 C23 H232 102.2(14) . . ? C20 C23 H233 114.2(9) . . ? H231 C23 H233 108.7(14) . . ? H232 C23 H233 108.7(15) . . ? C31 C30 C32 107.92(11) . . ? C31 C30 C33 106.43(12) . . ? C32 C30 C33 109.27(12) . . ? C31 C30 P1 110.91(10) . . ? C32 C30 P1 113.35(9) . . ? C33 C30 P1 108.73(9) . . ? C30 C31 H311 112.2(10) . . ? C30 C31 H312 115.0(10) . . ? H311 C31 H312 108.7(15) . . ? C30 C31 H313 104.9(10) . . ? H311 C31 H313 106.8(14) . . ? H312 C31 H313 108.9(14) . . ? C30 C32 H321 105.9(11) . . ? C30 C32 H322 112.0(10) . . ? H321 C32 H322 105.6(15) . . ? C30 C32 H323 112.4(11) . . ? H321 C32 H323 111.2(15) . . ? H322 C32 H323 109.6(14) . . ? C30 C33 H331 113.5(12) . . ? C30 C33 H332 112.4(11) . . ? H331 C33 H332 109.9(16) . . ? C30 C33 H333 109.7(11) . . ? H331 C33 H333 105.0(15) . . ? H332 C33 H333 105.7(15) . . ? 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 C30 P1 B1 O1 -157.69(9) . . . . ? C20 P1 B1 O1 80.80(11) . . . . ? C10 P1 B1 O1 -39.22(11) . . . . ? C30 P1 B1 O2 -38.76(11) . . . . ? C20 P1 B1 O2 -160.27(9) . . . . ? C10 P1 B1 O2 79.71(10) . . . . ? C30 P1 B1 Cl1 81.36(8) . . . . ? C20 P1 B1 Cl1 -40.15(9) . . . . ? C10 P1 B1 Cl1 -160.17(7) . . . . ? O2 B1 O1 C1 9.32(14) . . . . ? Cl1 B1 O1 C1 -108.55(10) . . . . ? P1 B1 O1 C1 130.27(10) . . . . ? O1 B1 O2 C2 -9.26(13) . . . . ? Cl1 B1 O2 C2 108.75(10) . . . . ? P1 B1 O2 C2 -130.77(9) . . . . ? B1 O1 C1 C6 177.10(13) . . . . ? B1 O1 C1 C2 -5.96(14) . . . . ? B1 O2 C2 C3 -175.40(13) . . . . ? B1 O2 C2 C1 5.79(13) . . . . ? O1 C1 C2 O2 0.08(15) . . . . ? C6 C1 C2 O2 177.26(12) . . . . ? O1 C1 C2 C3 -178.82(12) . . . . ? C6 C1 C2 C3 -1.6(2) . . . . ? O2 C2 C3 C4 -177.67(12) . . . . ? C1 C2 C3 C4 1.02(19) . . . . ? C2 C3 C4 C5 0.0(2) . . . . ? C3 C4 C5 C6 -0.5(2) . . . . ? O1 C1 C6 C5 177.74(13) . . . . ? C2 C1 C6 C5 1.1(2) . . . . ? C4 C5 C6 C1 0.0(2) . . . . ? C30 P1 C10 C12 76.37(10) . . . . ? C20 P1 C10 C12 -160.77(9) . . . . ? B1 P1 C10 C12 -40.41(11) . . . . ? C30 P1 C10 C11 -45.34(12) . . . . ? C20 P1 C10 C11 77.52(11) . . . . ? B1 P1 C10 C11 -162.12(10) . . . . ? C30 P1 C10 C13 -167.19(9) . . . . ? C20 P1 C10 C13 -44.32(11) . . . . ? B1 P1 C10 C13 76.03(10) . . . . ? C30 P1 C20 C22 79.65(11) . . . . ? C10 P1 C20 C22 -42.84(11) . . . . ? B1 P1 C20 C22 -160.75(10) . . . . ? C30 P1 C20 C23 -41.75(11) . . . . ? C10 P1 C20 C23 -164.24(9) . . . . ? B1 P1 C20 C23 77.85(10) . . . . ? C30 P1 C20 C21 -159.79(9) . . . . ? C10 P1 C20 C21 77.73(10) . . . . ? B1 P1 C20 C21 -40.19(11) . . . . ? C20 P1 C30 C31 -166.76(9) . . . . ? C10 P1 C30 C31 -44.31(11) . . . . ? B1 P1 C30 C31 71.86(11) . . . . ? C20 P1 C30 C32 -45.18(12) . . . . ? C10 P1 C30 C32 77.27(12) . . . . ? B1 P1 C30 C32 -166.57(10) . . . . ? C20 P1 C30 C33 76.55(11) . . . . ? C10 P1 C30 C33 -161.01(9) . . . . ? B1 P1 C30 C33 -44.84(11) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 29.12 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.241 _refine_diff_density_min -0.164 _refine_diff_density_rms 0.039 #=================================================END data_3e _database_code_CSD 154925 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-chloro-2-{tri(cyclohexyl)phosphino}-1,3,2-benzodioxaborole ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H37 B Cl O2 P' _chemical_formula_weight 434.77 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' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'P' 'P' 0.1023 0.0942 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P2(1)/n' 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 11.541(2) _cell_length_b 13.426(3) _cell_length_c 15.070(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.226(3) _cell_angle_gamma 90.00 _cell_volume 2333.3(8) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 832 _cell_measurement_theta_min 12.04 _cell_measurement_theta_max 23.06 _exptl_crystal_description irregular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.238 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 936 _exptl_absorpt_coefficient_mu 0.250 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7367 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS (G.M.Sheldrick,1998)' _exptl_special_details ; Five sets of \w scans (each scan 0.3\% in \w), each set at different \f and/or 2\q angles, nominally covered whole sphere of reciprocal space. The first 50 scans were repeated at the end of data collection, revealing no significant crystal decay. Crystal to detector distance 4.51 cm. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'SMART 1K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% 0 _diffrn_reflns_number 28034 _diffrn_reflns_av_R_equivalents 0.0403 _diffrn_reflns_av_sigmaI/netI 0.0292 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 31.63 _reflns_number_total 6574 _reflns_number_gt 5374 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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. ; _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^)+(0.0535P)^2^+0.7835P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6574 _refine_ls_number_parameters 410 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0528 _refine_ls_R_factor_gt 0.0395 _refine_ls_wR_factor_ref 0.1055 _refine_ls_wR_factor_gt 0.0973 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _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 P1 P 0.71572(3) 0.77223(2) 0.15375(2) 0.01734(9) Uani 1 1 d . . . Cl1 Cl 0.60594(3) 0.57237(3) 0.22538(2) 0.02550(9) Uani 1 1 d . . . B1 B 0.69280(13) 0.62868(11) 0.12509(10) 0.0204(3) Uani 1 1 d . . . O1 O 0.62590(8) 0.61738(7) 0.04558(6) 0.0222(2) Uani 1 1 d . . . O2 O 0.80133(8) 0.57464(7) 0.11028(7) 0.0232(2) Uani 1 1 d . . . C1 C 0.67845(12) 0.53998(10) -0.00001(9) 0.0212(3) Uani 1 1 d . . . C2 C 0.78227(12) 0.51437(10) 0.03828(9) 0.0216(3) Uani 1 1 d . . . C3 C 0.85080(14) 0.43766(11) 0.00542(11) 0.0275(3) Uani 1 1 d . . . H31 H 0.9238(17) 0.4208(14) 0.0315(13) 0.036(5) Uiso 1 1 d . . . C4 C 0.81085(15) 0.38640(12) -0.06894(11) 0.0313(3) Uani 1 1 d . . . H41 H 0.8582(17) 0.3356(16) -0.0953(13) 0.041(5) Uiso 1 1 d . . . C5 C 0.70791(16) 0.41260(12) -0.10698(10) 0.0321(3) Uani 1 1 d . . . H51 H 0.6840(17) 0.3769(15) -0.1582(14) 0.040(5) Uiso 1 1 d . . . C6 C 0.63879(14) 0.49041(11) -0.07313(10) 0.0267(3) Uani 1 1 d . . . H61 H 0.5687(17) 0.5074(14) -0.0955(12) 0.033(5) Uiso 1 1 d . . . C10 C 0.75215(12) 0.84255(10) 0.05142(9) 0.0205(3) Uani 1 1 d . . . H101 H 0.6751(15) 0.8527(13) 0.0256(11) 0.027(4) Uiso 1 1 d . . . C11 C 0.80221(15) 0.94670(11) 0.06915(10) 0.0277(3) Uani 1 1 d . . . H111 H 0.8799(17) 0.9386(14) 0.0923(13) 0.035(5) Uiso 1 1 d . . . H112 H 0.7534(17) 0.9837(15) 0.1120(13) 0.039(5) Uiso 1 1 d . . . C12 C 0.81066(17) 1.00702(13) -0.01703(11) 0.0345(4) Uani 1 1 d . . . H121 H 0.7323(18) 1.0191(15) -0.0358(13) 0.041(5) Uiso 1 1 d . . . H122 H 0.8396(19) 1.0736(17) -0.0061(14) 0.048(6) Uiso 1 1 d . . . C13 C 0.88241(16) 0.95353(13) -0.08882(11) 0.0345(4) Uani 1 1 d . . . H131 H 0.9614(18) 0.9483(15) -0.0726(13) 0.036(5) Uiso 1 1 d . . . H132 H 0.8835(17) 0.9913(15) -0.1430(14) 0.041(5) Uiso 1 1 d . . . C14 C 0.83812(15) 0.84795(13) -0.10443(10) 0.0304(3) Uani 1 1 d . . . H141 H 0.8884(17) 0.8158(15) -0.1463(13) 0.035(5) Uiso 1 1 d . . . H142 H 0.7609(19) 0.8521(16) -0.1303(14) 0.046(6) Uiso 1 1 d . . . C15 C 0.82877(14) 0.78720(12) -0.01828(10) 0.0260(3) Uani 1 1 d . . . H151 H 0.8003(17) 0.7245(15) -0.0279(13) 0.033(5) Uiso 1 1 d . . . H152 H 0.9088(19) 0.7761(15) 0.0040(14) 0.044(6) Uiso 1 1 d . . . C20 C 0.57716(11) 0.82047(10) 0.19993(9) 0.0190(2) Uani 1 1 d . . . H201 H 0.5565(16) 0.7732(13) 0.2487(12) 0.028(5) Uiso 1 1 d . . . C21 C 0.47965(12) 0.81267(11) 0.13319(10) 0.0234(3) Uani 1 1 d . . . H211 H 0.4963(15) 0.8619(14) 0.0826(12) 0.030(5) Uiso 1 1 d . . . H212 H 0.4766(16) 0.7459(14) 0.1074(12) 0.029(5) Uiso 1 1 d . . . C22 C 0.36265(12) 0.83809(11) 0.17891(10) 0.0251(3) Uani 1 1 d . . . H221 H 0.3423(16) 0.7891(14) 0.2260(12) 0.030(5) Uiso 1 1 d . . . H222 H 0.3005(16) 0.8352(14) 0.1336(12) 0.032(5) Uiso 1 1 d . . . C23 C 0.36406(14) 0.94051(13) 0.22290(13) 0.0333(4) Uani 1 1 d . . . H231 H 0.3742(18) 0.9933(16) 0.1750(14) 0.043(6) Uiso 1 1 d . . . H232 H 0.2933(18) 0.9576(15) 0.2533(14) 0.041(5) Uiso 1 1 d . . . C24 C 0.46287(14) 0.94821(14) 0.28721(13) 0.0363(4) Uani 1 1 d . . . H241 H 0.4477(18) 0.8992(15) 0.3371(14) 0.040(5) Uiso 1 1 d . . . H242 H 0.4654(17) 1.0148(16) 0.3127(14) 0.043(5) Uiso 1 1 d . . . C25 C 0.57971(13) 0.92533(12) 0.24036(12) 0.0296(3) Uani 1 1 d . . . H251 H 0.6440(17) 0.9310(14) 0.2833(13) 0.036(5) Uiso 1 1 d . . . H252 H 0.5925(16) 0.9752(15) 0.1942(13) 0.035(5) Uiso 1 1 d . . . C30 C 0.82585(11) 0.79367(10) 0.23644(9) 0.0207(3) Uani 1 1 d . . . H301 H 0.8296(16) 0.8669(15) 0.2432(12) 0.034(5) Uiso 1 1 d . . . C31 C 0.94727(12) 0.75826(13) 0.20379(10) 0.0272(3) Uani 1 1 d . . . H311 H 0.9724(16) 0.7916(14) 0.1453(13) 0.034(5) Uiso 1 1 d . . . H312 H 0.9442(16) 0.6869(15) 0.1941(12) 0.033(5) Uiso 1 1 d . . . C32 C 1.03731(13) 0.78189(14) 0.27306(11) 0.0325(3) Uani 1 1 d . . . H321 H 1.0457(17) 0.8553(16) 0.2797(13) 0.038(5) Uiso 1 1 d . . . H322 H 1.1126(17) 0.7563(14) 0.2516(13) 0.035(5) Uiso 1 1 d . . . C33 C 1.00393(14) 0.73710(14) 0.36357(11) 0.0338(4) Uani 1 1 d . . . H331 H 1.059(2) 0.7571(16) 0.4057(15) 0.049(6) Uiso 1 1 d . . . H332 H 1.0068(16) 0.6654(15) 0.3603(13) 0.036(5) Uiso 1 1 d . . . C34 C 0.88313(14) 0.77018(14) 0.39511(10) 0.0313(3) Uani 1 1 d . . . H341 H 0.8859(18) 0.8430(17) 0.4060(14) 0.046(6) Uiso 1 1 d . . . H342 H 0.8563(18) 0.7400(15) 0.4529(15) 0.044(6) Uiso 1 1 d . . . C35 C 0.79251(13) 0.74555(12) 0.32671(10) 0.0260(3) Uani 1 1 d . . . H351 H 0.7178(17) 0.7697(14) 0.3503(13) 0.034(5) Uiso 1 1 d . . . H352 H 0.7872(16) 0.6744(15) 0.3212(12) 0.034(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 P1 0.01678(15) 0.01760(16) 0.01727(15) -0.00116(11) -0.00419(12) 0.00016(11) Cl1 0.03023(18) 0.02221(16) 0.02379(16) 0.00285(12) -0.00238(13) -0.00313(12) B1 0.0206(7) 0.0198(7) 0.0202(7) 0.0000(5) -0.0060(5) 0.0006(5) O1 0.0222(5) 0.0213(5) 0.0223(5) -0.0024(4) -0.0089(4) 0.0008(4) O2 0.0223(5) 0.0214(5) 0.0252(5) -0.0049(4) -0.0086(4) 0.0025(4) C1 0.0236(6) 0.0189(6) 0.0210(6) 0.0002(5) -0.0017(5) -0.0035(5) C2 0.0230(6) 0.0189(6) 0.0227(6) -0.0012(5) -0.0018(5) -0.0023(5) C3 0.0264(7) 0.0233(7) 0.0329(8) 0.0001(6) 0.0036(6) 0.0004(5) C4 0.0383(8) 0.0227(7) 0.0337(8) -0.0060(6) 0.0109(7) -0.0021(6) C5 0.0444(9) 0.0274(7) 0.0246(7) -0.0064(6) 0.0029(6) -0.0126(7) C6 0.0309(7) 0.0261(7) 0.0226(6) 0.0005(5) -0.0040(6) -0.0092(6) C10 0.0204(6) 0.0225(6) 0.0183(6) 0.0000(5) -0.0037(5) -0.0016(5) C11 0.0363(8) 0.0230(7) 0.0236(7) 0.0006(5) -0.0028(6) -0.0062(6) C12 0.0447(10) 0.0268(8) 0.0317(8) 0.0069(6) -0.0051(7) -0.0067(7) C13 0.0375(9) 0.0386(9) 0.0273(8) 0.0071(7) -0.0017(7) -0.0120(7) C14 0.0321(8) 0.0381(9) 0.0210(6) -0.0015(6) 0.0002(6) -0.0068(7) C15 0.0280(7) 0.0264(7) 0.0235(7) -0.0034(5) 0.0013(6) -0.0027(6) C20 0.0168(6) 0.0193(6) 0.0206(6) -0.0011(5) -0.0043(5) 0.0019(5) C21 0.0199(6) 0.0250(7) 0.0246(6) -0.0020(5) -0.0071(5) 0.0015(5) C22 0.0190(6) 0.0268(7) 0.0290(7) -0.0005(6) -0.0055(5) 0.0013(5) C23 0.0218(7) 0.0305(8) 0.0472(10) -0.0098(7) -0.0055(7) 0.0074(6) C24 0.0243(7) 0.0385(9) 0.0457(10) -0.0219(8) -0.0046(7) 0.0045(6) C25 0.0219(7) 0.0258(7) 0.0405(8) -0.0127(6) -0.0064(6) 0.0008(5) C30 0.0180(6) 0.0225(6) 0.0211(6) -0.0029(5) -0.0060(5) 0.0013(5) C31 0.0190(6) 0.0369(8) 0.0254(7) -0.0078(6) -0.0052(5) 0.0029(6) C32 0.0193(7) 0.0448(9) 0.0325(8) -0.0089(7) -0.0094(6) 0.0028(6) C33 0.0280(8) 0.0399(9) 0.0324(8) -0.0064(7) -0.0149(6) 0.0095(7) C34 0.0288(8) 0.0419(9) 0.0223(7) -0.0036(6) -0.0102(6) 0.0054(6) C35 0.0223(7) 0.0335(8) 0.0215(6) 0.0004(6) -0.0062(5) 0.0013(6) _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 P1 C30 1.7686(13) . ? P1 C10 1.8698(14) . ? P1 C20 1.8835(14) . ? P1 B1 1.9905(16) . ? Cl1 B1 1.9946(17) . ? B1 O1 1.4083(16) . ? B1 O2 1.4721(18) . ? O1 C1 1.3971(17) . ? O2 C2 1.3646(16) . ? C1 C6 1.3519(19) . ? C1 C2 1.3539(18) . ? C2 C3 1.401(2) . ? C3 C4 1.379(2) . ? C3 H31 0.94(2) . ? C4 C5 1.346(2) . ? C4 H41 0.97(2) . ? C5 C6 1.421(2) . ? C5 H51 0.94(2) . ? C6 H61 0.894(19) . ? C10 C11 1.532(2) . ? C10 C15 1.584(2) . ? C10 H101 0.966(18) . ? C11 C12 1.537(2) . ? C11 H111 0.96(2) . ? C11 H112 1.00(2) . ? C12 C13 1.562(3) . ? C12 H121 0.95(2) . ? C12 H122 0.97(2) . ? C13 C14 1.522(2) . ? C13 H131 0.94(2) . ? C13 H132 0.96(2) . ? C14 C15 1.541(2) . ? C14 H141 0.97(2) . ? C14 H142 0.96(2) . ? C15 H151 0.91(2) . ? C15 H152 0.98(2) . ? C20 C21 1.4835(17) . ? C20 C25 1.5338(19) . ? C20 H201 1.006(18) . ? C21 C22 1.577(2) . ? C21 H211 1.033(18) . ? C21 H212 0.977(18) . ? C22 C23 1.526(2) . ? C22 H221 1.002(19) . ? C22 H222 0.971(18) . ? C23 C24 1.471(2) . ? C23 H231 1.02(2) . ? C23 H232 0.98(2) . ? C24 C25 1.576(2) . ? C24 H241 1.02(2) . ? C24 H242 0.97(2) . ? C25 H251 0.97(2) . ? C25 H252 0.98(2) . ? C30 C35 1.567(2) . ? C30 C31 1.577(2) . ? C30 H301 0.990(19) . ? C31 C32 1.4785(19) . ? C31 H311 1.040(19) . ? C31 H312 0.97(2) . ? C32 C33 1.553(3) . ? C32 H321 0.99(2) . ? C32 H322 1.00(2) . ? C33 C34 1.555(2) . ? C33 H331 0.92(2) . ? C33 H332 0.96(2) . ? C34 C35 1.4771(19) . ? C34 H341 0.99(2) . ? C34 H342 1.02(2) . ? C35 H351 1.00(2) . ? C35 H352 0.96(2) . ? 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 C30 P1 C10 108.69(6) . . ? C30 P1 C20 106.31(6) . . ? C10 P1 C20 110.64(6) . . ? C30 P1 B1 113.34(6) . . ? C10 P1 B1 110.01(6) . . ? C20 P1 B1 107.79(6) . . ? O1 B1 O2 105.04(11) . . ? O1 B1 P1 110.66(9) . . ? O2 B1 P1 113.79(9) . . ? O1 B1 Cl1 109.19(10) . . ? O2 B1 Cl1 112.56(9) . . ? P1 B1 Cl1 105.61(7) . . ? C1 O1 B1 105.33(10) . . ? C2 O2 B1 107.52(10) . . ? C6 C1 C2 119.23(14) . . ? C6 C1 O1 128.84(13) . . ? C2 C1 O1 111.92(11) . . ? C1 C2 O2 107.51(12) . . ? C1 C2 C3 122.59(13) . . ? O2 C2 C3 129.89(12) . . ? C4 C3 C2 118.60(14) . . ? C4 C3 H31 118.9(12) . . ? C2 C3 H31 122.5(12) . . ? C5 C4 C3 118.52(15) . . ? C5 C4 H41 120.8(12) . . ? C3 C4 H41 120.5(12) . . ? C4 C5 C6 122.53(14) . . ? C4 C5 H51 116.2(12) . . ? C6 C5 H51 121.3(12) . . ? C1 C6 C5 118.52(14) . . ? C1 C6 H61 117.0(12) . . ? C5 C6 H61 124.4(12) . . ? C11 C10 C15 109.11(12) . . ? C11 C10 P1 114.35(9) . . ? C15 C10 P1 117.33(10) . . ? C11 C10 H101 106.0(11) . . ? C15 C10 H101 109.2(10) . . ? P1 C10 H101 99.8(10) . . ? C10 C11 C12 111.67(12) . . ? C10 C11 H111 107.5(12) . . ? C12 C11 H111 106.2(12) . . ? C10 C11 H112 110.3(11) . . ? C12 C11 H112 109.7(11) . . ? H111 C11 H112 111.3(16) . . ? C11 C12 C13 113.31(14) . . ? C11 C12 H121 104.5(12) . . ? C13 C12 H121 113.3(12) . . ? C11 C12 H122 112.1(13) . . ? C13 C12 H122 110.8(13) . . ? H121 C12 H122 102.2(18) . . ? C14 C13 C12 110.57(14) . . ? C14 C13 H131 106.7(12) . . ? C12 C13 H131 112.9(12) . . ? C14 C13 H132 112.0(12) . . ? C12 C13 H132 111.7(12) . . ? H131 C13 H132 102.5(17) . . ? C13 C14 C15 113.38(13) . . ? C13 C14 H141 108.0(11) . . ? C15 C14 H141 112.0(11) . . ? C13 C14 H142 108.0(13) . . ? C15 C14 H142 106.2(13) . . ? H141 C14 H142 109.2(17) . . ? C14 C15 C10 111.69(13) . . ? C14 C15 H151 113.0(12) . . ? C10 C15 H151 109.4(12) . . ? C14 C15 H152 105.9(12) . . ? C10 C15 H152 112.7(12) . . ? H151 C15 H152 104.0(17) . . ? C21 C20 C25 109.66(11) . . ? C21 C20 P1 110.96(10) . . ? C25 C20 P1 117.32(10) . . ? C21 C20 H201 104.8(10) . . ? C25 C20 H201 106.9(10) . . ? P1 C20 H201 106.4(10) . . ? C20 C21 C22 109.17(12) . . ? C20 C21 H211 107.3(10) . . ? C22 C21 H211 111.8(10) . . ? C20 C21 H212 110.4(11) . . ? C22 C21 H212 110.7(11) . . ? H211 C21 H212 107.4(15) . . ? C23 C22 C21 112.94(12) . . ? C23 C22 H221 106.4(11) . . ? C21 C22 H221 113.3(11) . . ? C23 C22 H222 109.6(11) . . ? C21 C22 H222 107.8(11) . . ? H221 C22 H222 106.6(15) . . ? C24 C23 C22 110.14(13) . . ? C24 C23 H231 108.1(12) . . ? C22 C23 H231 108.5(12) . . ? C24 C23 H232 108.3(12) . . ? C22 C23 H232 114.8(12) . . ? H231 C23 H232 106.8(17) . . ? C23 C24 C25 110.23(14) . . ? C23 C24 H241 106.8(12) . . ? C25 C24 H241 112.3(12) . . ? C23 C24 H242 109.6(12) . . ? C25 C24 H242 110.0(12) . . ? H241 C24 H242 107.8(16) . . ? C20 C25 C24 110.69(13) . . ? C20 C25 H251 109.9(11) . . ? C24 C25 H251 109.4(12) . . ? C20 C25 H252 110.2(11) . . ? C24 C25 H252 109.9(11) . . ? H251 C25 H252 106.7(16) . . ? C35 C30 C31 113.43(11) . . ? C35 C30 P1 110.52(9) . . ? C31 C30 P1 110.74(9) . . ? C35 C30 H301 109.4(11) . . ? C31 C30 H301 107.2(11) . . ? P1 C30 H301 105.2(11) . . ? C32 C31 C30 108.90(12) . . ? C32 C31 H311 107.1(10) . . ? C30 C31 H311 114.6(10) . . ? C32 C31 H312 109.8(11) . . ? C30 C31 H312 108.5(11) . . ? H311 C31 H312 107.9(15) . . ? C31 C32 C33 110.21(14) . . ? C31 C32 H321 110.2(11) . . ? C33 C32 H321 108.8(11) . . ? C31 C32 H322 107.1(11) . . ? C33 C32 H322 113.5(11) . . ? H321 C32 H322 106.9(16) . . ? C32 C33 C34 114.44(13) . . ? C32 C33 H331 107.6(14) . . ? C34 C33 H331 108.2(14) . . ? C32 C33 H332 109.4(12) . . ? C34 C33 H332 109.5(12) . . ? H331 C33 H332 107.5(17) . . ? C35 C34 C33 109.97(13) . . ? C35 C34 H341 110.7(12) . . ? C33 C34 H341 108.0(12) . . ? C35 C34 H342 106.1(12) . . ? C33 C34 H342 117.0(12) . . ? H341 C34 H342 105.0(17) . . ? C34 C35 C30 108.81(13) . . ? C34 C35 H351 106.0(11) . . ? C30 C35 H351 114.8(11) . . ? C34 C35 H352 108.9(11) . . ? C30 C35 H352 110.6(11) . . ? H351 C35 H352 107.5(15) . . ? 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 C30 P1 B1 O1 -165.71(10) . . . . ? C10 P1 B1 O1 -43.80(12) . . . . ? C20 P1 B1 O1 76.92(11) . . . . ? C30 P1 B1 O2 -47.72(12) . . . . ? C10 P1 B1 O2 74.19(11) . . . . ? C20 P1 B1 O2 -165.09(9) . . . . ? C30 P1 B1 Cl1 76.24(8) . . . . ? C10 P1 B1 Cl1 -161.85(6) . . . . ? C20 P1 B1 Cl1 -41.13(8) . . . . ? O2 B1 O1 C1 15.39(14) . . . . ? P1 B1 O1 C1 138.60(10) . . . . ? Cl1 B1 O1 C1 -105.56(10) . . . . ? O1 B1 O2 C2 -16.12(14) . . . . ? P1 B1 O2 C2 -137.30(10) . . . . ? Cl1 B1 O2 C2 102.59(11) . . . . ? B1 O1 C1 C6 169.24(15) . . . . ? B1 O1 C1 C2 -10.11(15) . . . . ? C6 C1 C2 O2 -179.63(13) . . . . ? O1 C1 C2 O2 -0.22(16) . . . . ? C6 C1 C2 C3 -0.4(2) . . . . ? O1 C1 C2 C3 179.06(13) . . . . ? B1 O2 C2 C1 10.11(15) . . . . ? B1 O2 C2 C3 -169.10(15) . . . . ? C1 C2 C3 C4 0.1(2) . . . . ? O2 C2 C3 C4 179.20(14) . . . . ? C2 C3 C4 C5 0.3(2) . . . . ? C3 C4 C5 C6 -0.4(2) . . . . ? C2 C1 C6 C5 0.2(2) . . . . ? O1 C1 C6 C5 -179.08(13) . . . . ? C4 C5 C6 C1 0.2(2) . . . . ? C30 P1 C10 C11 -40.20(12) . . . . ? C20 P1 C10 C11 76.17(12) . . . . ? B1 P1 C10 C11 -164.84(10) . . . . ? C30 P1 C10 C15 89.46(11) . . . . ? C20 P1 C10 C15 -154.17(9) . . . . ? B1 P1 C10 C15 -35.18(12) . . . . ? C15 C10 C11 C12 56.13(17) . . . . ? P1 C10 C11 C12 -170.24(12) . . . . ? C10 C11 C12 C13 -55.78(19) . . . . ? C11 C12 C13 C14 51.86(19) . . . . ? C12 C13 C14 C15 -51.42(19) . . . . ? C13 C14 C15 C10 54.66(18) . . . . ? C11 C10 C15 C14 -55.65(15) . . . . ? P1 C10 C15 C14 172.27(10) . . . . ? C30 P1 C20 C21 176.03(10) . . . . ? C10 P1 C20 C21 58.20(11) . . . . ? B1 P1 C20 C21 -62.13(11) . . . . ? C30 P1 C20 C25 48.92(12) . . . . ? C10 P1 C20 C25 -68.92(12) . . . . ? B1 P1 C20 C25 170.75(10) . . . . ? C25 C20 C21 C22 -57.41(16) . . . . ? P1 C20 C21 C22 171.38(9) . . . . ? C20 C21 C22 C23 56.43(16) . . . . ? C21 C22 C23 C24 -55.79(19) . . . . ? C22 C23 C24 C25 55.9(2) . . . . ? C21 C20 C25 C24 59.96(17) . . . . ? P1 C20 C25 C24 -172.29(11) . . . . ? C23 C24 C25 C20 -59.10(19) . . . . ? C10 P1 C30 C35 173.93(10) . . . . ? C20 P1 C30 C35 54.81(11) . . . . ? B1 P1 C30 C35 -63.42(12) . . . . ? C10 P1 C30 C31 -59.50(12) . . . . ? C20 P1 C30 C31 -178.62(10) . . . . ? B1 P1 C30 C31 63.15(12) . . . . ? C35 C30 C31 C32 -57.72(17) . . . . ? P1 C30 C31 C32 177.34(12) . . . . ? C30 C31 C32 C33 53.91(18) . . . . ? C31 C32 C33 C34 -55.84(19) . . . . ? C32 C33 C34 C35 56.3(2) . . . . ? C33 C34 C35 C30 -54.96(18) . . . . ? C31 C30 C35 C34 58.28(16) . . . . ? P1 C30 C35 C34 -176.67(11) . . . . ? _diffrn_measured_fraction_theta_max 0.837 _diffrn_reflns_theta_full 31.63 _diffrn_measured_fraction_theta_full 0.837 _refine_diff_density_max 0.470 _refine_diff_density_min -0.330 _refine_diff_density_rms 0.055 #=================================================END data_3h _database_code_CSD 154926 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-chloro-2-(triethylamino)-1,3,2-benzodioxaborole ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H19 B Cl N O2' _chemical_formula_weight 255.54 _ccdc_compound_id '3h' _ccdc_biological_activity '?' _ccdc_polymorph '?' _ccdc_disorder 'none' _ccdc_comments '?' 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 6.6037(3) _cell_length_b 13.3458(7) _cell_length_c 15.0557(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1326.88(11) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 856 _cell_measurement_theta_min 18.85 _cell_measurement_theta_max 30.51 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.71 _exptl_crystal_size_mid 0.53 _exptl_crystal_size_min 0.45 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.279 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.277 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.927 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; Four sets of \w scans (each scan 0.3\% in \w), each set at different \f and angles, nominally covered whole sphere of reciprocal space. The first 50 scans were repeated at the end of data collection, revealing no significant crystal decay. Crystal to detector distance 4.51 cm. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'SMART 1K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% 0 _diffrn_reflns_number 15865 _diffrn_reflns_av_R_equivalents 0.0152 _diffrn_reflns_av_sigmaI/netI 0.0092 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 30.44 _reflns_number_total 3762 _reflns_number_gt 3697 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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. ; _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^)+(0.0396P)^2^+0.2019P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(3) _refine_ls_number_reflns 3762 _refine_ls_number_parameters 230 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0239 _refine_ls_R_factor_gt 0.0234 _refine_ls_wR_factor_ref 0.0640 _refine_ls_wR_factor_gt 0.0632 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _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 0.83294(13) 0.50656(6) 0.50442(5) 0.01743(14) Uani 1 1 d . . . Cl1 Cl 0.98479(4) 0.395168(17) 0.359024(14) 0.02505(6) Uani 1 1 d . . . B1 B 0.81644(16) 0.50057(7) 0.39564(6) 0.01659(17) Uani 1 1 d . . . O1 O 0.60714(11) 0.48385(5) 0.36868(5) 0.01913(13) Uani 1 1 d . . . O2 O 0.88053(10) 0.59513(5) 0.35699(4) 0.01836(12) Uani 1 1 d . . . C1 C 0.55425(14) 0.56536(7) 0.31790(6) 0.01737(16) Uani 1 1 d . . . C2 C 0.71681(14) 0.63111(7) 0.31087(6) 0.01644(16) Uani 1 1 d . . . C3 C 0.70256(16) 0.72014(7) 0.26439(6) 0.02042(17) Uani 1 1 d . . . H31 H 0.817(2) 0.7620(12) 0.2605(10) 0.029(4) Uiso 1 1 d . . . C4 C 0.51448(18) 0.74230(7) 0.22520(6) 0.0251(2) Uani 1 1 d . . . H41 H 0.497(2) 0.8025(11) 0.1943(10) 0.031(4) Uiso 1 1 d . . . C5 C 0.35272(17) 0.67704(9) 0.23270(7) 0.0272(2) Uani 1 1 d . . . H51 H 0.223(2) 0.6927(12) 0.2073(11) 0.034(4) Uiso 1 1 d . . . C6 C 0.36934(15) 0.58574(8) 0.27945(7) 0.02367(19) Uani 1 1 d . . . H61 H 0.260(3) 0.5448(12) 0.2844(12) 0.035(4) Uiso 1 1 d . . . C10 C 0.67442(15) 0.58076(8) 0.53482(6) 0.02123(18) Uani 1 1 d . . . H101 H 0.709(2) 0.6440(12) 0.5060(10) 0.025(3) Uiso 1 1 d . . . H102 H 0.551(2) 0.5575(10) 0.5107(9) 0.020(3) Uiso 1 1 d . . . C11 C 0.65925(19) 0.59506(10) 0.63508(7) 0.0328(2) Uani 1 1 d . . . H111 H 0.573(3) 0.6505(13) 0.6475(12) 0.042(4) Uiso 1 1 d . . . H112 H 0.594(3) 0.5376(13) 0.6645(11) 0.039(4) Uiso 1 1 d . . . H113 H 0.785(3) 0.6135(13) 0.6641(11) 0.041(4) Uiso 1 1 d . . . C20 C 0.7996(2) 0.40569(8) 0.54895(7) 0.0274(2) Uani 1 1 d . . . H201 H 0.915(2) 0.3670(13) 0.5307(11) 0.035(4) Uiso 1 1 d . . . H202 H 0.811(2) 0.4166(11) 0.6139(9) 0.022(3) Uiso 1 1 d . . . C21 C 0.5999(3) 0.35500(11) 0.52991(9) 0.0441(4) Uani 1 1 d . . . H211 H 0.583(3) 0.3424(16) 0.4665(14) 0.061(6) Uiso 1 1 d . . . H212 H 0.483(3) 0.3946(15) 0.5480(13) 0.050(5) Uiso 1 1 d . . . H213 H 0.601(3) 0.2942(15) 0.5635(13) 0.053(5) Uiso 1 1 d . . . C30 C 1.04411(16) 0.53931(8) 0.53361(7) 0.02393(19) Uani 1 1 d . . . H301 H 1.138(2) 0.5020(12) 0.5026(12) 0.032(4) Uiso 1 1 d . . . H302 H 1.047(2) 0.5245(12) 0.5969(11) 0.033(4) Uiso 1 1 d . . . C31 C 1.09934(19) 0.64899(9) 0.52084(8) 0.0303(2) Uani 1 1 d . . . H311 H 1.095(3) 0.6666(13) 0.4582(12) 0.040(4) Uiso 1 1 d . . . H312 H 1.232(3) 0.6588(15) 0.5468(12) 0.047(5) Uiso 1 1 d . . . H313 H 1.011(3) 0.6903(13) 0.5534(11) 0.043(4) 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 N1 0.0226(3) 0.0149(3) 0.0147(3) 0.0002(3) -0.0014(3) 0.0015(3) Cl1 0.03594(12) 0.02059(10) 0.01862(10) -0.00121(7) 0.00207(9) 0.00949(9) B1 0.0223(4) 0.0141(4) 0.0134(4) 0.0009(3) -0.0011(3) 0.0008(3) O1 0.0231(3) 0.0172(3) 0.0171(3) 0.0028(2) -0.0026(3) -0.0044(2) O2 0.0189(3) 0.0178(3) 0.0183(3) 0.0047(2) -0.0026(2) -0.0018(2) C1 0.0214(4) 0.0181(4) 0.0126(3) 0.0001(3) 0.0008(3) 0.0007(3) C2 0.0196(4) 0.0167(4) 0.0130(3) -0.0001(3) 0.0000(3) 0.0015(3) C3 0.0306(5) 0.0162(4) 0.0145(4) 0.0009(3) 0.0007(3) 0.0010(3) C4 0.0380(5) 0.0212(4) 0.0163(4) 0.0011(3) -0.0025(4) 0.0112(4) C5 0.0271(5) 0.0337(5) 0.0209(4) -0.0007(4) -0.0039(4) 0.0126(4) C6 0.0197(4) 0.0311(5) 0.0202(4) -0.0002(4) -0.0010(3) 0.0007(4) C10 0.0225(4) 0.0231(4) 0.0181(4) -0.0031(3) 0.0010(3) 0.0043(3) C11 0.0379(5) 0.0410(6) 0.0195(4) -0.0089(4) 0.0030(4) 0.0065(5) C20 0.0470(6) 0.0185(4) 0.0166(4) 0.0054(3) -0.0008(4) -0.0005(4) C21 0.0703(10) 0.0337(6) 0.0283(6) 0.0129(5) -0.0079(6) -0.0264(7) C30 0.0224(4) 0.0267(5) 0.0227(4) -0.0032(3) -0.0069(4) 0.0041(4) C31 0.0276(5) 0.0337(5) 0.0295(5) -0.0032(4) -0.0075(4) -0.0079(4) _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 1.5120(12) . ? N1 C20 1.5198(13) . ? N1 C30 1.5261(13) . ? N1 B1 1.6433(13) . ? Cl1 B1 1.8758(10) . ? B1 O2 1.4527(11) . ? B1 O1 1.4576(13) . ? O1 C1 1.3748(11) . ? O2 C2 1.3717(10) . ? C1 C6 1.3785(13) . ? C1 C2 1.3905(13) . ? C2 C3 1.3821(12) . ? C3 C4 1.4065(15) . ? C4 C5 1.3829(17) . ? C5 C6 1.4114(15) . ? C10 C11 1.5247(14) . ? C20 C21 1.5097(19) . ? C30 C31 1.5207(16) . ? 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 C20 110.26(8) . . ? C10 N1 C30 110.97(7) . . ? C20 N1 C30 105.01(8) . . ? C10 N1 B1 106.72(7) . . ? C20 N1 B1 112.76(7) . . ? C30 N1 B1 111.20(8) . . ? O2 B1 O1 107.32(7) . . ? O2 B1 N1 109.73(7) . . ? O1 B1 N1 110.35(7) . . ? O2 B1 Cl1 111.16(7) . . ? O1 B1 Cl1 111.43(6) . . ? N1 B1 Cl1 106.86(6) . . ? C1 O1 B1 105.94(7) . . ? C2 O2 B1 106.10(7) . . ? O1 C1 C6 127.93(9) . . ? O1 C1 C2 110.21(8) . . ? C6 C1 C2 121.83(9) . . ? O2 C2 C3 127.66(8) . . ? O2 C2 C1 110.43(8) . . ? C3 C2 C1 121.90(9) . . ? C2 C3 C4 116.96(9) . . ? C5 C4 C3 121.03(9) . . ? C4 C5 C6 121.62(9) . . ? C1 C6 C5 116.66(9) . . ? N1 C10 C11 115.29(8) . . ? C21 C20 N1 116.08(10) . . ? C31 C30 N1 117.28(8) . . ? 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 C10 N1 B1 O2 67.63(9) . . . . ? C20 N1 B1 O2 -171.16(8) . . . . ? C30 N1 B1 O2 -53.52(10) . . . . ? C10 N1 B1 O1 -50.43(9) . . . . ? C20 N1 B1 O1 70.78(10) . . . . ? C30 N1 B1 O1 -171.58(7) . . . . ? C10 N1 B1 Cl1 -171.74(6) . . . . ? C20 N1 B1 Cl1 -50.53(10) . . . . ? C30 N1 B1 Cl1 67.11(8) . . . . ? O2 B1 O1 C1 -0.53(9) . . . . ? N1 B1 O1 C1 119.01(8) . . . . ? Cl1 B1 O1 C1 -122.44(7) . . . . ? O1 B1 O2 C2 0.37(9) . . . . ? N1 B1 O2 C2 -119.56(8) . . . . ? Cl1 B1 O2 C2 122.45(7) . . . . ? B1 O1 C1 C6 -177.79(9) . . . . ? B1 O1 C1 C2 0.49(9) . . . . ? B1 O2 C2 C3 178.47(9) . . . . ? B1 O2 C2 C1 -0.08(10) . . . . ? O1 C1 C2 O2 -0.27(10) . . . . ? C6 C1 C2 O2 178.13(8) . . . . ? O1 C1 C2 C3 -178.92(8) . . . . ? C6 C1 C2 C3 -0.51(14) . . . . ? O2 C2 C3 C4 -177.55(9) . . . . ? C1 C2 C3 C4 0.85(13) . . . . ? C2 C3 C4 C5 -0.49(14) . . . . ? C3 C4 C5 C6 -0.21(16) . . . . ? O1 C1 C6 C5 177.89(9) . . . . ? C2 C1 C6 C5 -0.21(14) . . . . ? C4 C5 C6 C1 0.57(15) . . . . ? C20 N1 C10 C11 55.27(11) . . . . ? C30 N1 C10 C11 -60.65(11) . . . . ? B1 N1 C10 C11 178.06(9) . . . . ? C10 N1 C20 C21 61.19(12) . . . . ? C30 N1 C20 C21 -179.21(10) . . . . ? B1 N1 C20 C21 -57.99(13) . . . . ? C10 N1 C30 C31 -44.67(11) . . . . ? C20 N1 C30 C31 -163.79(9) . . . . ? B1 N1 C30 C31 73.95(11) . . . . ? _diffrn_measured_fraction_theta_max 0.955 _diffrn_reflns_theta_full 30.44 _diffrn_measured_fraction_theta_full 0.955 _refine_diff_density_max 0.282 _refine_diff_density_min -0.173 _refine_diff_density_rms 0.038 #==============================================END