# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2006 data_global _journal_name_full 'New J.Chem.(Nouv.J.Chim.)' #======================================================================== # SUBMISSION DETAILS _journal_coden_Cambridge 0440 _publ_contact_author_name 'Sergiusz Lulinski' _publ_contact_author_address ; Dr Sergiusz Lulinski, Department of Chemistry Warsaw University of Technology, Noakowskiego 3, PL-00-664 Warszawa Poland ; _publ_contact_author_phone 48(22)6607575 _publ_contact_author_fax 48(22)6282741 _publ_contact_author_email serek@ch.pw.edu.pl #============================================================================ # 2. TITLE AND AUTHOR LIST _publ_section_title ; A Fine Tautomeric Equilibrium between Functionalized 2-Formylphenylboronic Acids and Corresponding 1,3-Dihydro-1,3-dihydroxy[c][2,1]oxaboroles ; loop_ _publ_author_name _publ_author_address S.Lulinski ; Department of Chemistry Warsaw University of Technology, Noakowskiego 3, PL-00-664 Warszawa e-mail: serek@ch.pw.edu.pl Phone: +48 22 6607575 Poland ; I.Madura ; Department of Chemistry Warsaw University of Technology, Noakowskiego 3, PL-00-664 Warszawa Poland e-mail: izabela@chemix.ch.pw.edu.pl Phone: +48 22 6225186 ; J.Serwatowski ; Department of Chemistry Warsaw University of Technology, Noakowskiego 3, PL-00-664 Warszawa Poland e-mail: serwat@ch.pw.edu.pl Phone: +48 22 6607273 ; H.Szatylowicz ; Department of Chemistry Warsaw University of Technology, Noakowskiego 3, PL-00-664 Warszawa Poland e-mail: halina@ch.pw.edu.pl Phone: +48 22 6607755 ; J.Zachara ; Department of Chemistry Warsaw University of Technology, Noakowskiego 3, PL-00-664 Warszawa Poland e-mail: janzac@ch.pw.edu.pl Phone: +48 22 6225186 ; # Attachment 'B611195E_Cpds1&5.CIF' # Sergiusz Lulinski, Izabela Madura, Janusz Serwatowski, # Halina Szaty\/lowicz and Janusz Zachara # # A Tautomeric Equilibrium between Functionalized # 2-Formylphenylboronic Acids and Corresponding # 1,3-Dihydro-1,3-dihydroxybenzo[c][2,1]oxaboroles #========================================================================= # COMPOUND 1 data_FH_comp1 _database_code_depnum_ccdc_archive 'CCDC 614639' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3-Fluoro-2-formyl-phenylboronic acid ; _chemical_name_common '3-Fluoro-2-formyl-phenylboronic acid' _chemical_melting_point ? _chemical_formula_moiety 'C7 H6 B F O3' _chemical_formula_sum 'C7 H6 B F O3' _chemical_formula_weight 167.93 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall -P_1 _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.2136(9) _cell_length_b 7.6191(8) _cell_length_c 8.1010(11) _cell_angle_alpha 102.960(10) _cell_angle_beta 106.797(10) _cell_angle_gamma 111.387(9) _cell_volume 368.75(8) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 47 _cell_measurement_theta_min 7.40 _cell_measurement_theta_max 16.87 _exptl_crystal_description prism _exptl_crystal_colour white _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.512 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 172 _exptl_absorpt_coefficient_mu 0.130 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'four-circle diffractometer' _diffrn_measurement_device_type 'Siemens P3' _diffrn_measurement_method 'profile data from \q/2\q scans' _diffrn_detector 'scintillation counter' _diffrn_standards_number 2 _diffrn_standards_interval_count 70 _diffrn_standards_decay_% 3.3 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 1 -3 1 2 -2 -1 _diffrn_reflns_number 1415 _diffrn_reflns_av_R_equivalents 0.0116 _diffrn_reflns_av_sigmaI/netI 0.0112 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.83 _diffrn_reflns_theta_max 25.04 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.04 _diffrn_measured_fraction_theta_full 1.000 _diffrn_special_details ; 2\q scan width: 2.0\% plus K\a1-K\a2 separation; variable scan speed: 4.9 to 29.3\%(2\q)/min, background/peak time ratio 1.0 ; _reflns_number_total 1302 _reflns_number_gt 1143 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Siemens P3 software' _computing_cell_refinement 'Siemens P3 software' _computing_data_reduction 'XDISK, Siemens P3 software' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; ORTEP III (Burnett, Johnson, 1996) & DIAMOND v2.1 (Brandenburg, 1999) ; _computing_publication_material ; SHELXL-97 (Sheldrick, 1997) & PLATON99 (Spek, 1999) ; _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^)+(0.0426P)^2^+0.0738P] 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 refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.019(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1302 _refine_ls_number_parameters 134 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0370 _refine_ls_R_factor_gt 0.0327 _refine_ls_wR_factor_ref 0.0907 _refine_ls_wR_factor_gt 0.0874 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _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 F1 F 0.37773(18) 0.91867(14) 0.71984(14) 0.0764(4) Uani 1 1 d . . . O1 O 0.1232(2) 0.04322(17) 0.26353(17) 0.0694(4) Uani 1 1 d . . . O2 O 0.0751(2) 0.24299(18) 0.09422(15) 0.0678(4) Uani 1 1 d . . . O3 O 0.2080(2) 0.62933(16) 0.19775(15) 0.0665(4) Uani 1 1 d . . . C1 C 0.2148(2) 0.3923(2) 0.45552(18) 0.0417(3) Uani 1 1 d . . . C2 C 0.2675(2) 0.6003(2) 0.49613(19) 0.0428(3) Uani 1 1 d . . . C3 C 0.3293(2) 0.7204(2) 0.6793(2) 0.0516(4) Uani 1 1 d . . . C4 C 0.3408(3) 0.6508(3) 0.8216(2) 0.0604(4) Uani 1 1 d . . . C5 C 0.2890(3) 0.4499(3) 0.7813(2) 0.0598(4) Uani 1 1 d . . . C6 C 0.2284(2) 0.3241(2) 0.6024(2) 0.0499(4) Uani 1 1 d . . . C7 C 0.2634(3) 0.7037(2) 0.3629(2) 0.0539(4) Uani 1 1 d . . . B1 B 0.1353(3) 0.2225(2) 0.2599(2) 0.0470(4) Uani 1 1 d . . . H1 H 0.067(4) -0.049(3) 0.155(3) 0.097(7) Uiso 1 1 d . . . H2 H 0.106(3) 0.373(4) 0.110(3) 0.093(7) Uiso 1 1 d . . . H3 H 0.314(3) 0.848(3) 0.419(3) 0.074(5) Uiso 1 1 d . . . H4 H 0.385(3) 0.743(3) 0.944(3) 0.079(6) Uiso 1 1 d . . . H5 H 0.291(3) 0.391(3) 0.874(2) 0.069(5) Uiso 1 1 d . . . H6 H 0.192(3) 0.185(3) 0.578(2) 0.057(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 F1 0.1030(8) 0.0464(5) 0.0647(6) 0.0081(4) 0.0281(6) 0.0312(5) O1 0.1155(10) 0.0476(6) 0.0515(7) 0.0216(5) 0.0301(7) 0.0451(7) O2 0.1214(11) 0.0497(7) 0.0456(6) 0.0228(5) 0.0350(6) 0.0488(7) O3 0.1030(9) 0.0512(6) 0.0536(7) 0.0286(5) 0.0347(6) 0.0364(6) C1 0.0422(7) 0.0433(7) 0.0449(7) 0.0195(6) 0.0195(6) 0.0217(6) C2 0.0423(7) 0.0427(7) 0.0450(7) 0.0170(6) 0.0189(6) 0.0200(6) C3 0.0525(8) 0.0436(8) 0.0507(8) 0.0116(6) 0.0173(7) 0.0203(7) C4 0.0638(10) 0.0655(10) 0.0390(8) 0.0106(7) 0.0157(7) 0.0259(8) C5 0.0653(10) 0.0705(11) 0.0439(8) 0.0279(8) 0.0198(7) 0.0296(8) C6 0.0561(8) 0.0498(8) 0.0479(8) 0.0244(7) 0.0204(7) 0.0255(7) C7 0.0656(10) 0.0405(8) 0.0554(9) 0.0205(7) 0.0233(7) 0.0237(7) B1 0.0589(9) 0.0434(9) 0.0485(9) 0.0214(7) 0.0264(8) 0.0273(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 F1 C3 1.3556(17) . ? O1 B1 1.3440(19) . ? O1 H1 0.86(2) . ? O2 B1 1.3494(19) . ? O2 H2 0.90(2) . ? O3 C7 1.2066(19) . ? C1 C6 1.3940(19) . ? C1 C2 1.4210(19) . ? C1 B1 1.590(2) . ? C2 C3 1.396(2) . ? C2 C7 1.472(2) . ? C3 C4 1.367(2) . ? C4 C5 1.370(2) . ? C4 H4 0.96(2) . ? C5 C6 1.384(2) . ? C5 H5 0.958(18) . ? C6 H6 0.949(17) . ? C7 H3 0.965(19) . ? 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 H1 113.4(15) . . ? B1 O2 H2 110.7(14) . . ? C6 C1 C2 117.15(13) . . ? C6 C1 B1 114.80(12) . . ? C2 C1 B1 128.03(12) . . ? C3 C2 C1 117.73(13) . . ? C3 C2 C7 116.03(13) . . ? C1 C2 C7 126.25(13) . . ? F1 C3 C4 117.22(13) . . ? F1 C3 C2 118.42(13) . . ? C4 C3 C2 124.34(14) . . ? C3 C4 C5 117.60(14) . . ? C3 C4 H4 119.2(11) . . ? C5 C4 H4 123.2(11) . . ? C4 C5 C6 120.55(15) . . ? C4 C5 H5 121.7(11) . . ? C6 C5 H5 117.7(11) . . ? C5 C6 C1 122.62(14) . . ? C5 C6 H6 119.0(10) . . ? C1 C6 H6 118.3(10) . . ? O3 C7 C2 127.51(14) . . ? O3 C7 H3 118.6(11) . . ? C2 C7 H3 113.9(11) . . ? O1 B1 O2 118.62(14) . . ? O1 B1 C1 115.86(13) . . ? O2 B1 C1 125.50(13) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag O1 H1 O2 0.86(2) 1.92(2) 2.7740(17) 175(3) 2_555 yes O2 H2 O3 0.90(3) 1.70(3) 2.5801(18) 165(2) 1_555 yes _refine_diff_density_max 0.180 _refine_diff_density_min -0.122 _refine_diff_density_rms 0.026 #==================================================================== # COMPOUND 5 data_BrBr_comp5 _database_code_depnum_ccdc_archive 'CCDC 614640' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3,5-Dibromo-2-formyl-phenylboronic acid monohydrate ; _chemical_name_common '3,5-Dibromo-2-formyl-phenylboronic acid monohydrate' _chemical_melting_point ? _chemical_formula_moiety 'C7 H5 B Br2 O3, H2 O' _chemical_formula_sum 'C7 H7 B Br2 O4' _chemical_formula_weight 325.76 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 triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall -P_1 _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.0559(16) _cell_length_b 8.3747(18) _cell_length_c 9.656(2) _cell_angle_alpha 89.986(17) _cell_angle_beta 99.607(18) _cell_angle_gamma 108.329(17) _cell_volume 533.2(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 30 _cell_measurement_theta_min 7.60 _cell_measurement_theta_max 16.54 _exptl_crystal_description 'transparent flattened prism' _exptl_crystal_colour white _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.029 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 312 _exptl_absorpt_coefficient_mu 7.584 _exptl_absorpt_correction_type gaussian _exptl_absorpt_correction_T_min 0.14908 _exptl_absorpt_correction_T_max 0.57544 _exptl_absorpt_process_details 'analytical SHELX76 (Sheldrick, 1976)' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 -1 1 0.04 0 1 -1 0.04 0 0 1 0.10 0 0 -1 0.10 1 -1 0 0.28 -1 1 0 0.22 -1 0 -1 0.29 1 0 1 0.30 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'four-circle diffractometer' _diffrn_measurement_device_type 'Siemens P3' _diffrn_measurement_method 'profile data from \q/2\q scans' _diffrn_detector 'scintillation counter' _diffrn_standards_number 2 _diffrn_standards_interval_count 70 _diffrn_standards_decay_% 0 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 2 2 -2 1 -3 -2 _diffrn_reflns_number 4077 _diffrn_reflns_av_R_equivalents 0.0169 _diffrn_reflns_av_sigmaI/netI 0.0206 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 25.05 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 1.000 _diffrn_special_details ; 2\q scan width: 2.0\% plus K\a1-K\a2 separation; variable scan speed: 4.9 to 29.3\%(2\q)/min, background/peak time ratio 1.0 ; _reflns_number_total 1877 _reflns_number_gt 1609 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens P3 software' _computing_cell_refinement 'Siemens P3 software' _computing_data_reduction 'XDISK, Siemens P3 software' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; ORTEP III (Burnett, Johnson, 1996) & DIAMOND v2.1 (Brandenburg, 1999) ; _computing_publication_material ; SHELXL-97 (Sheldrick, 1997) & PLATON99 (Spek, 1999) ; _refine_special_details ; The structure was solved by direct methods using SHELXS-97 (Sheldrick, 1990), which readly revealed the positions of all Br, C, B and O atoms. All non-hydrogen atoms were refined with anisotropic thermal parameters. The H-atoms of water were located from the Fourier-difference map and isotropically refined. The remaining H-atoms were introduced in calculated positions with fixed isotropic displacement parameter equal to 1.2 times the value of the equivalent isotropic displacement parameter of the parent atom. 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^)+(0.0358P)^2^+0.2039P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1877 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0327 _refine_ls_R_factor_gt 0.0253 _refine_ls_wR_factor_ref 0.0652 _refine_ls_wR_factor_gt 0.0622 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _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 0.33349(5) 0.81699(4) 0.41561(4) 0.05599(13) Uani 1 1 d . . . Br2 Br 0.21526(6) 0.24308(5) 0.72905(3) 0.06132(14) Uani 1 1 d . . . O1 O 0.2433(3) 0.1101(3) 0.1306(2) 0.0437(5) Uani 1 1 d . . . H1 H 0.1892 0.0388 0.0657 0.052 Uiso 1 1 calc R . . O2 O -0.0843(3) 0.1291(2) 0.0881(2) 0.0390(5) Uani 1 1 d . . . H2 H -0.1511 0.1816 0.1177 0.047 Uiso 1 1 calc R . . O3 O 0.2243(4) 0.4663(3) 0.0518(2) 0.0577(6) Uani 1 1 d . . . C1 C 0.1688(4) 0.3040(3) 0.3002(3) 0.0312(6) Uani 1 1 d . . . C2 C 0.2186(4) 0.4791(3) 0.2933(3) 0.0324(6) Uani 1 1 d . . . C3 C 0.2624(4) 0.5793(3) 0.4172(3) 0.0351(6) Uani 1 1 d . . . C4 C 0.2599(4) 0.5103(4) 0.5466(3) 0.0406(7) Uani 1 1 d . . . H4 H 0.2884 0.5781 0.6286 0.049 Uiso 1 1 calc R . . C5 C 0.2140(4) 0.3382(4) 0.5514(3) 0.0376(7) Uani 1 1 d . . . C6 C 0.1674(4) 0.2348(4) 0.4301(3) 0.0367(6) Uani 1 1 d . . . H6 H 0.1352 0.1187 0.4362 0.044 Uiso 1 1 calc R . . C7 C 0.2327(5) 0.5503(4) 0.1557(3) 0.0451(7) Uani 1 1 d . . . H7 H 0.2487 0.6643 0.1478 0.054 Uiso 1 1 calc R . . B1 B 0.1071(5) 0.1814(4) 0.1619(3) 0.0340(7) Uani 1 1 d . . . O4 O 0.6574(4) 0.2809(3) 0.1450(3) 0.0470(6) Uani 1 1 d . . . H4A H 0.671(8) 0.367(7) 0.089(5) 0.105(18) Uiso 1 1 d . . . H4B H 0.543(8) 0.235(6) 0.145(5) 0.084(17) 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 0.0579(2) 0.02876(17) 0.0769(3) -0.01434(15) 0.00445(18) 0.01126(14) Br2 0.0632(2) 0.0805(3) 0.03250(18) 0.01026(16) 0.00921(15) 0.01159(19) O1 0.0362(11) 0.0442(12) 0.0471(13) -0.0196(10) 0.0009(9) 0.0109(9) O2 0.0358(11) 0.0399(11) 0.0386(11) -0.0168(9) 0.0014(9) 0.0112(9) O3 0.0861(18) 0.0501(13) 0.0330(12) 0.0005(10) 0.0140(12) 0.0143(13) C1 0.0285(13) 0.0318(14) 0.0302(14) -0.0060(11) 0.0035(11) 0.0060(11) C2 0.0304(14) 0.0301(14) 0.0338(15) -0.0047(11) 0.0026(12) 0.0071(11) C3 0.0317(14) 0.0283(13) 0.0415(16) -0.0093(12) 0.0032(12) 0.0058(11) C4 0.0374(15) 0.0470(17) 0.0332(15) -0.0171(13) 0.0041(13) 0.0089(14) C5 0.0356(15) 0.0451(17) 0.0282(14) -0.0003(12) 0.0066(12) 0.0067(13) C6 0.0391(15) 0.0305(14) 0.0368(16) -0.0020(12) 0.0055(13) 0.0066(12) C7 0.0552(19) 0.0332(15) 0.0420(17) 0.0037(13) 0.0052(15) 0.0091(14) B1 0.0385(17) 0.0281(15) 0.0324(16) -0.0063(13) 0.0061(14) 0.0065(14) O4 0.0446(14) 0.0505(14) 0.0484(14) -0.0004(11) 0.0123(11) 0.0164(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 Br1 C3 1.895(3) . ? Br2 C5 1.891(3) . ? O1 B1 1.353(4) . ? O1 H1 0.8200 . ? O2 B1 1.353(4) . ? O2 H2 0.8200 . ? O3 C7 1.208(4) . ? C1 C6 1.382(4) . ? C1 C2 1.401(4) . ? C1 B1 1.598(4) . ? C2 C3 1.395(4) . ? C2 C7 1.463(4) . ? C3 C4 1.377(4) . ? C4 C5 1.377(4) . ? C4 H4 0.9300 . ? C5 C6 1.386(4) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? O4 H4A 0.89(6) . ? O4 H4B 0.78(5) . ? 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 H1 109.5 . . ? B1 O2 H2 109.5 . . ? C6 C1 C2 119.1(2) . . ? C6 C1 B1 119.0(2) . . ? C2 C1 B1 121.9(3) . . ? C3 C2 C1 119.4(3) . . ? C3 C2 C7 122.5(3) . . ? C1 C2 C7 118.1(2) . . ? C4 C3 C2 121.5(3) . . ? C4 C3 Br1 116.9(2) . . ? C2 C3 Br1 121.5(2) . . ? C3 C4 C5 118.2(2) . . ? C3 C4 H4 120.9 . . ? C5 C4 H4 120.9 . . ? C4 C5 C6 121.7(3) . . ? C4 C5 Br2 118.4(2) . . ? C6 C5 Br2 119.9(2) . . ? C1 C6 C5 120.1(3) . . ? C1 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? O3 C7 C2 122.3(3) . . ? O3 C7 H7 118.8 . . ? C2 C7 H7 118.8 . . ? O1 B1 O2 119.3(2) . . ? O1 B1 C1 118.1(2) . . ? O2 B1 C1 121.8(2) . . ? H4A O4 H4B 110(5) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag O1 H1 O2 0.82 1.93 2.744(3) 175 2_555 yes O2 H2 O4 0.82 1.85 2.652(4) 167 1_455 yes O4 H4A O3 0.89(5) 2.01(5) 2.865(3) 161(5) 2_665 yes O4 H4B O1 0.78(6) 2.02(6) 2.800(4) 176(5) 1_555 yes C4 H4 O4 0.93 2.40 3.324(4) 172 2_666 yes loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_2 B1 O3 2.561(4) 1_555 _refine_diff_density_max 0.367 _refine_diff_density_min -0.398 _refine_diff_density_rms 0.065 #===END #========================================================================= # COMPOUND 3 data_comp3-II _database_code_depnum_ccdc_archive 'CCDC 626865' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,3-Dihydro-1,3-dihydroxy-4-bromo-2,1-benzoxaborole monohydrate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7H6B1Br1O3 , H2O' _chemical_formula_sum 'C7 H8 B Br O4' _chemical_formula_weight 246.85 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' Br Br -0.2901 2.4595 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M Cc _symmetry_space_group_name_Hall 'C -2yc' _symmetry_Int_Tables_number 9 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 11.159(3) _cell_length_b 11.116(2) _cell_length_c 29.383(7) _cell_angle_alpha 90.00 _cell_angle_beta 94.473(18) _cell_angle_gamma 90.00 _cell_volume 3633.6(14) _cell_formula_units_Z 16 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 47 _cell_measurement_theta_min 6.26 _cell_measurement_theta_max 16.46 _exptl_crystal_description 'square plates' _exptl_crystal_colour white _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.805 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1952 _exptl_absorpt_coefficient_mu 4.501 _exptl_absorpt_correction_type gaussian _exptl_absorpt_correction_T_min 0.24031 _exptl_absorpt_correction_T_max 0.43515 _exptl_absorpt_process_details 'analytical SHELX76 (Sheldrick, 1976)' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 0 1 0.115 0 0 -1 0.115 1 1 0 0.19 -1 -1 0 0.19 1 1 -2 0.18 -1 -1 2 0.18 1 -1 -2 0.19 -1 1 2 0.19 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'four-circle diffractometer' _diffrn_measurement_device_type 'Siemens P3' _diffrn_measurement_method 'profile data from \q/2\q scans' _diffrn_detector 'scintillation counter' _diffrn_standards_number 2 _diffrn_standards_interval_count 70 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 2 2 7 1 -5 -1 _diffrn_reflns_number 3296 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0399 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 2.59 _diffrn_reflns_theta_max 25.04 _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 25.04 _diffrn_measured_fraction_theta_full 0.970 _diffrn_special_details ; 2\q scan width: 1.8\% plus K\a1-K\a2 separation; variable scan speed: 4.9 to 29.3\%(2\q)/min, background/peak time ratio 0.7 ; _reflns_number_total 3296 _reflns_number_gt 2557 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Siemens P3 software' _computing_cell_refinement 'Siemens P3 software' _computing_data_reduction 'XDISK, Siemens P3 software' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; ORTEP III (Burnett, Johnson, 1996) & DIAMOND v2.1 (Brandenburg, 1999) ; _computing_publication_material ; SHELXL-97 (Sheldrick, 1997) & PLATON99 (Spek, 1999) ; _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. Only the heaviest atoms (Br, O) were anisotropically refined. It was determined that the molecules are arranged into layers in the (0 0 1) plane. After the analysis of the residual maxima on the Fourier maps the disorder (layer-stacking faults) was modeled as a superposition of two identical layers shifted by 1/2a (or 1/2b) vector. The positional and thermal parameters of the major layer component were refined while the minor one was introduced entirely as a rigid group (including water oxygens) with a common isotropic thermal parameter. The geometry of the rigid group was subsequently corrected according to changes of the major group on successive stages of the refinement. The final INS file contained the following instruction lines: TITL boh1h in Cc CELL 0.71073 11.1589 11.1160 29.3829 90.00 94.473 90.00 ZERR 16.00 0.0026 0.0024 0.0065 0.00 0.018 0.00 LATT -7 SYMM X, -Y, .5+Z SFAC C H B Br O UNIT 112 128 16 16 64 L.S. 10 BOND HTAB FMAP 2 ACTA FLAT_mol 0.02 Br1 > O2 PLAN 20 SAME_mol 0.02 0.02 Br1 > O4 SADI_mol 0.005 C3 C4 C4 C5 ISOR_mol 0.02 O2 TWIN WGHT 0.074800 39.000000 BASF 0.20911 FVAR 0.40680 0.88642 0.05354 0.04397 RESI mol 1 PART 1 BR1 4 0.062932 -0.123275 0.295851 21.00000 0.04620 0.06892 = 0.03737 -0.00405 -0.01020 0.01839 B1 3 0.382962 -0.146777 0.432389 21.00000 0.02811 C1 1 0.352477 -0.219406 0.387621 21.00000 0.02741 C2 1 0.252228 -0.160274 0.367002 21.00000 0.03011 C3 1 0.197938 -0.199667 0.325234 21.00000 0.03524 C4 1 0.245518 -0.298487 0.305051 21.00000 0.02980 AFIX 43 H4 2 0.209802 -0.325619 0.277280 21.00000 -1.20000 AFIX 0 C5 1 0.344172 -0.358445 0.324606 21.00000 0.04151 AFIX 43 H5 2 0.374504 -0.424873 0.310066 21.00000 -1.20000 AFIX 0 C6 1 0.398701 -0.319382 0.366336 21.00000 0.03266 AFIX 43 H6 2 0.465322 -0.359699 0.379837 21.00000 -1.20000 AFIX 0 C7 1 0.216922 -0.055522 0.394742 21.00000 0.03078 AFIX 13 H7 2 0.231305 0.017247 0.377143 21.00000 -1.20000 AFIX 0 O1 5 0.469716 -0.159519 0.466849 21.00000 0.04504 0.05702 = 0.02675 -0.01567 -0.01579 0.01904 AFIX 83 H1 2 0.505303 -0.223207 0.463811 21.00000 -1.50000 AFIX 0 O2 5 0.302149 -0.054722 0.434268 21.00000 0.03765 0.04292 = 0.04326 -0.01498 -0.01261 0.00784 O3 5 0.102027 -0.048462 0.407672 21.00000 0.02908 0.04860 = 0.04759 -0.00065 0.00073 0.00669 AFIX 83 H3 2 0.089682 -0.104519 0.424834 21.00000 -1.50000 AFIX 0 O4 5 0.477855 -0.004478 0.540057 21.00000 0.03212 0.04303 = 0.03522 -0.00701 -0.00527 0.02362 RESI mol 2 PART 1 BR1 4 0.294777 0.521179 0.705933 21.00000 0.06339 0.04698 = 0.03747 -0.00619 -0.00205 0.02245 ............. ............. RESI mol 3 PART 1 BR1 4 0.930942 0.370804 0.704763 21.00000 0.05238 0.06780 = 0.03992 -0.00450 -0.01296 0.02228 ............. ............. RESI mol 4 PART 1 BR1 4 0.720222 -0.258195 0.293686 21.00000 0.05665 0.05470 = 0.03592 -0.01622 -0.00551 0.01529 ............. ............. RESI rot 5 PART 2 AFIX 6 rem Rigid group containing 4 molecules + 4 water rem mol1 BR11 4 -0.432279 -0.126950 0.293547 -21.00000 31.00000 B11 3 -0.112374 -0.148790 0.430187 -21.00000 41.00000 C11 1 -0.142438 -0.221757 0.385460 -21.00000 41.00000 C21 1 -0.242807 -0.162909 0.364738 -21.00000 41.00000 C31 1 -0.296978 -0.202955 0.322956 -21.00000 41.00000 C41 1 -0.248833 -0.301607 0.302980 -21.00000 41.00000 H41 2 -0.284267 -0.328992 0.275200 -21.00000 -1.20000 C51 1 -0.150232 -0.361179 0.322594 -21.00000 41.00000 H51 2 -0.119787 -0.427704 0.308150 -21.00000 -1.20000 C61 1 -0.095863 -0.321684 0.364229 -21.00000 41.00000 H61 2 -0.029045 -0.361660 0.377746 -21.00000 -1.20000 C71 1 -0.278891 -0.058556 0.392493 -21.00000 41.00000 H71 2 -0.264855 0.014294 0.374891 -21.00000 -1.20000 O11 5 -0.025550 -0.160982 0.464650 -21.00000 41.00000 H11 2 0.010316 -0.224534 0.461665 -21.00000 -1.50000 O21 5 -0.193689 -0.057092 0.432015 -21.00000 41.00000 O31 5 -0.393754 -0.051836 0.405386 -21.00000 41.00000 H31 2 -0.405940 -0.107890 0.422567 -21.00000 -1.50000 O41 5 -0.018301 -0.005952 0.537760 -21.00000 41.00000 rem mol2 BR12 4 -0.203666 0.519500 0.703341 -21.00000 31.00000 ............. ............. rem mol3 BR13 4 0.433162 0.371694 0.702372 -21.00000 31.00000 ............. ............. rem mol4 BR14 4 0.225532 -0.259340 0.291604 -21.00000 31.00000 ............. ............. HKLF 4 END ; _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^)+(0.0748P)^2^+39.0000P] 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_abs_structure_Flack 0.21(5) _refine_ls_number_reflns 3296 _refine_ls_number_parameters 319 _refine_ls_number_restraints 278 _refine_ls_R_factor_all 0.0809 _refine_ls_R_factor_gt 0.0593 _refine_ls_wR_factor_ref 0.1617 _refine_ls_wR_factor_gt 0.1481 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.002 _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 Br1_1 Br 0.0629(3) -0.12328(18) 0.29585(9) 0.0515(5) Uani 0.886(3) 1 d PD A 1 B1_1 B 0.3830(7) -0.1468(8) 0.4324(3) 0.028(4) Uiso 0.886(3) 1 d PD A 1 C1_1 C 0.3525(6) -0.2194(7) 0.3876(2) 0.027(3) Uiso 0.886(3) 1 d PD A 1 C2_1 C 0.2522(6) -0.1603(7) 0.3670(2) 0.030(3) Uiso 0.886(3) 1 d PD A 1 C3_1 C 0.1979(7) -0.1997(7) 0.3252(3) 0.035(3) Uiso 0.886(3) 1 d PD A 1 C4_1 C 0.2455(7) -0.2985(7) 0.3051(3) 0.030(4) Uiso 0.886(3) 1 d PD A 1 H4_1 H 0.2098 -0.3256 0.2773 0.036 Uiso 0.886(3) 1 calc PR A 1 C5_1 C 0.3442(8) -0.3584(9) 0.3246(3) 0.042(4) Uiso 0.886(3) 1 d PD A 1 H5_1 H 0.3745 -0.4249 0.3101 0.050 Uiso 0.886(3) 1 calc PR A 1 C6_1 C 0.3987(8) -0.3194(8) 0.3663(3) 0.033(3) Uiso 0.886(3) 1 d PD A 1 H6_1 H 0.4653 -0.3597 0.3798 0.039 Uiso 0.886(3) 1 calc PR A 1 C7_1 C 0.2169(7) -0.0555(8) 0.3947(3) 0.031(3) Uiso 0.886(3) 1 d PD A 1 H7_1 H 0.2313 0.0172 0.3771 0.037 Uiso 0.886(3) 1 calc PR A 1 O1_1 O 0.4697(7) -0.1595(9) 0.4668(3) 0.044(3) Uani 0.886(3) 1 d PD A 1 H1_1 H 0.5053 -0.2232 0.4638 0.066 Uiso 0.886(3) 1 calc PR A 1 O2_1 O 0.3021(7) -0.0547(7) 0.4343(3) 0.042(3) Uani 0.886(3) 1 d PDU A 1 O3_1 O 0.1020(7) -0.0485(10) 0.4077(4) 0.042(3) Uani 0.886(3) 1 d PD A 1 H3_1 H 0.0897 -0.1045 0.4248 0.063 Uiso 0.886(3) 1 calc PR A 1 O4_1 O 0.4779(9) -0.0045(9) 0.5401(4) 0.037(2) Uani 0.886(3) 1 d P A 1 Br1_2 Br 0.2948(3) 0.52118(15) 0.70593(9) 0.0496(5) Uani 0.886(3) 1 d PD A 1 B1_2 B 0.2914(8) 0.2335(8) 0.5683(3) 0.032(4) Uiso 0.886(3) 1 d PD A 1 C1_2 C 0.3730(7) 0.2534(7) 0.6128(3) 0.031(3) Uiso 0.886(3) 1 d PD A 1 C2_2 C 0.3173(7) 0.3490(6) 0.6340(2) 0.031(3) Uiso 0.886(3) 1 d PD A 1 C3_2 C 0.3666(7) 0.3926(6) 0.6760(3) 0.028(3) Uiso 0.886(3) 1 d PD A 1 C4_2 C 0.4698(7) 0.3409(7) 0.6959(3) 0.039(4) Uiso 0.886(3) 1 d PD A 1 H4_2 H 0.5029 0.3701 0.7238 0.047 Uiso 0.886(3) 1 calc PR A 1 C5_2 C 0.5251(9) 0.2468(8) 0.6754(3) 0.037(4) Uiso 0.886(3) 1 d PD A 1 H5_2 H 0.5944 0.2128 0.6896 0.044 Uiso 0.886(3) 1 calc PR A 1 C6_2 C 0.4772(8) 0.2026(9) 0.6336(3) 0.034(3) Uiso 0.886(3) 1 d PD A 1 H6_2 H 0.5148 0.1394 0.6196 0.041 Uiso 0.886(3) 1 calc PR A 1 C7_2 C 0.2067(8) 0.3904(7) 0.6064(3) 0.038(4) Uiso 0.886(3) 1 d PD A 1 H7_2 H 0.1378 0.3716 0.6239 0.045 Uiso 0.886(3) 1 calc PR A 1 O1_2 O 0.2980(9) 0.1540(7) 0.5335(3) 0.049(3) Uani 0.886(3) 1 d PD A 1 H1_2 H 0.3613 0.1164 0.5370 0.073 Uiso 0.886(3) 1 calc PR A 1 O2_2 O 0.1983(7) 0.3140(7) 0.5666(3) 0.040(3) Uani 0.886(3) 1 d PDU A 1 O3_2 O 0.1956(10) 0.5080(7) 0.5931(3) 0.039(3) Uani 0.886(3) 1 d PD A 1 H3_2 H 0.2582 0.5303 0.5828 0.058 Uiso 0.886(3) 1 calc PR A 1 O4_2 O 0.1270(10) 0.1642(9) 0.4601(4) 0.035(2) Uani 0.886(3) 1 d P A 1 Br1_3 Br 0.9309(3) 0.37080(18) 0.70476(10) 0.0542(5) Uani 0.886(3) 1 d PD A 1 B1_3 B 0.6210(8) 0.4045(9) 0.5662(3) 0.039(4) Uiso 0.886(3) 1 d PD A 1 C1_3 C 0.6495(6) 0.4757(7) 0.6111(2) 0.028(3) Uiso 0.886(3) 1 d PD A 1 C2_3 C 0.7471(6) 0.4144(7) 0.6325(2) 0.030(3) Uiso 0.886(3) 1 d PD A 1 C3_3 C 0.7987(7) 0.4527(7) 0.6747(3) 0.029(3) Uiso 0.886(3) 1 d PD A 1 C4_3 C 0.7516(8) 0.5519(7) 0.6948(3) 0.046(4) Uiso 0.886(3) 1 d PD A 1 H4_3 H 0.7858 0.5777 0.7230 0.056 Uiso 0.886(3) 1 calc PR A 1 C5_3 C 0.6556(8) 0.6142(9) 0.6744(3) 0.038(4) Uiso 0.886(3) 1 d PD A 1 H5_3 H 0.6255 0.6812 0.6886 0.046 Uiso 0.886(3) 1 calc PR A 1 C6_3 C 0.6038(9) 0.5766(8) 0.6323(3) 0.035(3) Uiso 0.886(3) 1 d PD A 1 H6_3 H 0.5389 0.6183 0.6182 0.042 Uiso 0.886(3) 1 calc PR A 1 C7_3 C 0.7835(7) 0.3090(7) 0.6052(3) 0.028(3) Uiso 0.886(3) 1 d PD A 1 H7_3 H 0.7681 0.2359 0.6225 0.034 Uiso 0.886(3) 1 calc PR A 1 O1_3 O 0.5367(7) 0.4196(9) 0.5311(3) 0.051(3) Uani 0.886(3) 1 d PD A 1 H1_3 H 0.5024 0.4841 0.5339 0.076 Uiso 0.886(3) 1 calc PR A 1 O2_3 O 0.7002(6) 0.3104(7) 0.5647(2) 0.037(3) Uani 0.886(3) 1 d PDU A 1 O3_3 O 0.8987(7) 0.3024(9) 0.5920(3) 0.037(3) Uani 0.886(3) 1 d PD A 1 H3_3 H 0.9126 0.3616 0.5767 0.055 Uiso 0.886(3) 1 calc PR A 1 O4_3 O 0.5288(10) 0.2620(12) 0.4602(4) 0.047(3) Uani 0.886(3) 1 d P A 1 Br1_4 Br 0.7202(3) -0.25819(16) 0.29369(9) 0.0496(5) Uani 0.886(3) 1 d PD A 1 B1_4 B 0.7108(8) 0.0196(8) 0.4334(3) 0.035(4) Uiso 0.886(3) 1 d PD A 1 C1_4 C 0.6307(7) 0.0008(7) 0.3885(3) 0.033(3) Uiso 0.886(3) 1 d PD A 1 C2_4 C 0.6889(7) -0.0916(6) 0.3665(2) 0.030(3) Uiso 0.886(3) 1 d PD A 1 C3_4 C 0.6422(7) -0.1340(6) 0.3240(3) 0.032(3) Uiso 0.886(3) 1 d PD A 1 C4_4 C 0.5383(7) -0.0839(7) 0.3040(3) 0.033(4) Uiso 0.886(3) 1 d PD A 1 H4_4 H 0.5070 -0.1117 0.2756 0.040 Uiso 0.886(3) 1 calc PR A 1 C5_4 C 0.4799(9) 0.0066(9) 0.3253(3) 0.045(4) Uiso 0.886(3) 1 d PD A 1 H5_4 H 0.4096 0.0392 0.3113 0.054 Uiso 0.886(3) 1 calc PR A 1 C6_4 C 0.5252(8) 0.0500(8) 0.3677(3) 0.035(3) Uiso 0.886(3) 1 d PD A 1 H6_4 H 0.4855 0.1112 0.3821 0.042 Uiso 0.886(3) 1 calc PR A 1 C7_4 C 0.8008(7) -0.1322(7) 0.3942(3) 0.028(3) Uiso 0.886(3) 1 d PD A 1 H7_4 H 0.8705 -0.1132 0.3772 0.033 Uiso 0.886(3) 1 calc PR A 1 O1_4 O 0.7026(8) 0.0957(7) 0.4689(3) 0.044(3) Uani 0.886(3) 1 d PD A 1 H1_4 H 0.6470 0.1428 0.4631 0.066 Uiso 0.886(3) 1 calc PR A 1 O2_4 O 0.8062(7) -0.0587(7) 0.4347(3) 0.040(3) Uani 0.886(3) 1 d PDU A 1 O3_4 O 0.8072(9) -0.2525(7) 0.4067(3) 0.033(2) Uani 0.886(3) 1 d PD A 1 H3_4 H 0.7438 -0.2728 0.4168 0.049 Uiso 0.886(3) 1 calc PR A 1 O4_4 O 0.8725(10) 0.0918(10) 0.5395(4) 0.044(3) Uani 0.886(3) 1 d P A 1 Br11_5 Br -0.432(2) -0.1269(11) 0.2935(7) 0.054(2) Uiso 0.114(3) 1 d PG A 2 B11_5 B -0.112(2) -0.1488(8) 0.4302(7) 0.044(4) Uiso 0.114(3) 1 d PG A 2 C11_5 C -0.142(2) -0.2218(9) 0.3855(7) 0.044(4) Uiso 0.114(3) 1 d PG A 2 C21_5 C -0.243(2) -0.1629(9) 0.3647(7) 0.044(4) Uiso 0.114(3) 1 d PG A 2 C31_5 C -0.297(2) -0.2030(10) 0.3230(7) 0.044(4) Uiso 0.114(3) 1 d PG A 2 C41_5 C -0.249(2) -0.3016(10) 0.3030(7) 0.044(4) Uiso 0.114(3) 1 d PG A 2 H41_5 H -0.2843 -0.3290 0.2752 0.053 Uiso 0.114(3) 1 d PG A 2 C51_5 C -0.150(2) -0.3612(9) 0.3226(7) 0.044(4) Uiso 0.114(3) 1 d PG A 2 H51_5 H -0.1198 -0.4277 0.3082 0.053 Uiso 0.114(3) 1 d PG A 2 C61_5 C -0.096(2) -0.3217(9) 0.3642(7) 0.044(4) Uiso 0.114(3) 1 d PG A 2 H61_5 H -0.0290 -0.3617 0.3777 0.053 Uiso 0.114(3) 1 d PG A 2 C71_5 C -0.279(2) -0.0586(9) 0.3925(7) 0.044(4) Uiso 0.114(3) 1 d PG A 2 H71_5 H -0.2649 0.0143 0.3749 0.053 Uiso 0.114(3) 1 d PG A 2 O11_5 O -0.026(2) -0.1610(8) 0.4647(7) 0.044(4) Uiso 0.114(3) 1 d PG A 2 H11_5 H 0.0103 -0.2245 0.4617 0.066 Uiso 0.114(3) 1 d PG A 2 O21_5 O -0.194(2) -0.0571(8) 0.4320(7) 0.044(4) Uiso 0.114(3) 1 d PG A 2 O31_5 O -0.394(2) -0.0518(10) 0.4054(7) 0.044(4) Uiso 0.114(3) 1 d PG A 2 H31_5 H -0.4059 -0.1079 0.4226 0.066 Uiso 0.114(3) 1 d PG A 2 O41_5 O -0.018(2) -0.0060(8) 0.5378(7) 0.044(4) Uiso 0.114(3) 1 d PG A 2 Br12_5 Br -0.204(2) 0.5195(11) 0.7033(7) 0.054(2) Uiso 0.114(3) 1 d PG A 2 B12_5 B -0.206(2) 0.2312(9) 0.5659(7) 0.044(4) Uiso 0.114(3) 1 d PG A 2 C12_5 C -0.124(2) 0.2515(9) 0.6104(7) 0.044(4) Uiso 0.114(3) 1 d PG A 2 C22_5 C -0.181(2) 0.3469(10) 0.6315(7) 0.044(4) Uiso 0.114(3) 1 d PG A 2 C32_5 C -0.131(2) 0.3910(10) 0.6736(7) 0.044(4) Uiso 0.114(3) 1 d PG A 2 C42_5 C -0.028(2) 0.3394(10) 0.6934(7) 0.044(4) Uiso 0.114(3) 1 d PG A 2 H42_5 H 0.0049 0.3687 0.7213 0.053 Uiso 0.114(3) 1 d PG A 2 C52_5 C 0.028(2) 0.2458(10) 0.6730(7) 0.044(4) Uiso 0.114(3) 1 d PG A 2 H52_5 H 0.0974 0.2123 0.6871 0.053 Uiso 0.114(3) 1 d PG A 2 C62_5 C -0.020(2) 0.2011(9) 0.6313(7) 0.044(4) Uiso 0.114(3) 1 d PG A 2 H62_5 H 0.0176 0.1378 0.6174 0.053 Uiso 0.114(3) 1 d PG A 2 C72_5 C -0.291(2) 0.3882(10) 0.6039(7) 0.044(4) Uiso 0.114(3) 1 d PG A 2 H72_5 H -0.3598 0.3694 0.6214 0.053 Uiso 0.114(3) 1 d PG A 2 O12_5 O -0.199(2) 0.1516(9) 0.5312(7) 0.044(4) Uiso 0.114(3) 1 d PG A 2 H12_5 H -0.1356 0.1142 0.5347 0.066 Uiso 0.114(3) 1 d PG A 2 O22_5 O -0.299(2) 0.3116(10) 0.5641(7) 0.044(4) Uiso 0.114(3) 1 d PG A 2 O32_5 O -0.303(2) 0.5056(10) 0.5904(7) 0.044(4) Uiso 0.114(3) 1 d PG A 2 H32_5 H -0.2400 0.5281 0.5802 0.066 Uiso 0.114(3) 1 d PG A 2 O42_5 O -0.370(2) 0.1612(10) 0.4577(7) 0.044(4) Uiso 0.114(3) 1 d PG A 2 Br13_5 Br 0.433(2) 0.3717(11) 0.7024(7) 0.054(2) Uiso 0.114(3) 1 d PG A 2 B13_5 B 0.123(2) 0.4038(8) 0.5637(7) 0.044(4) Uiso 0.114(3) 1 d PG A 2 C13_5 C 0.152(2) 0.4752(9) 0.6086(7) 0.044(4) Uiso 0.114(3) 1 d PG A 2 C23_5 C 0.249(2) 0.4141(9) 0.6300(7) 0.044(4) Uiso 0.114(3) 1 d PG A 2 C33_5 C 0.301(2) 0.4530(10) 0.6723(7) 0.044(4) Uiso 0.114(3) 1 d PG A 2 C43_5 C 0.253(2) 0.5522(10) 0.6922(7) 0.044(4) Uiso 0.114(3) 1 d PG A 2 H43_5 H 0.2872 0.5783 0.7203 0.053 Uiso 0.114(3) 1 d PG A 2 C53_5 C 0.157(2) 0.6141(10) 0.6717(7) 0.044(4) Uiso 0.114(3) 1 d PG A 2 H53_5 H 0.1268 0.6811 0.6860 0.053 Uiso 0.114(3) 1 d PG A 2 C63_5 C 0.105(2) 0.5761(9) 0.6297(7) 0.044(4) Uiso 0.114(3) 1 d PG A 2 H63_5 H 0.0403 0.6175 0.6156 0.053 Uiso 0.114(3) 1 d PG A 2 C73_5 C 0.286(2) 0.3091(9) 0.6028(7) 0.044(4) Uiso 0.114(3) 1 d PG A 2 H73_5 H 0.2712 0.2359 0.6200 0.053 Uiso 0.114(3) 1 d PG A 2 O13_5 O 0.039(2) 0.4186(8) 0.5286(7) 0.044(4) Uiso 0.114(3) 1 d PG A 2 H13_5 H 0.0045 0.4830 0.5314 0.066 Uiso 0.114(3) 1 d PG A 2 O23_5 O 0.203(2) 0.3101(9) 0.5622(7) 0.044(4) Uiso 0.114(3) 1 d PG A 2 O33_5 O 0.401(2) 0.3029(10) 0.5896(7) 0.044(4) Uiso 0.114(3) 1 d PG A 2 H33_5 H 0.4150 0.3622 0.5742 0.066 Uiso 0.114(3) 1 d PG A 2 O43_5 O 0.032(2) 0.2607(8) 0.4577(7) 0.044(4) Uiso 0.114(3) 1 d PG A 2 Br14_5 Br 0.226(2) -0.2593(11) 0.2916(8) 0.054(2) Uiso 0.114(3) 1 d PG A 2 B14_5 B 0.215(2) 0.0188(9) 0.4311(7) 0.044(4) Uiso 0.114(3) 1 d PG A 2 C14_5 C 0.135(2) -0.0004(9) 0.3862(7) 0.044(4) Uiso 0.114(3) 1 d PG A 2 C24_5 C 0.194(2) -0.0925(10) 0.3642(7) 0.044(4) Uiso 0.114(3) 1 d PG A 2 C34_5 C 0.147(2) -0.1352(10) 0.3217(7) 0.044(4) Uiso 0.114(3) 1 d PG A 2 C44_5 C 0.043(2) -0.0855(10) 0.3018(7) 0.044(4) Uiso 0.114(3) 1 d PG A 2 H44_5 H 0.0115 -0.1136 0.2736 0.053 Uiso 0.114(3) 1 d PG A 2 C54_5 C -0.016(2) 0.0048(9) 0.3230(7) 0.044(4) Uiso 0.114(3) 1 d PG A 2 H54_5 H -0.0863 0.0370 0.3090 0.053 Uiso 0.114(3) 1 d PG A 2 C64_5 C 0.029(2) 0.0484(9) 0.3654(7) 0.044(4) Uiso 0.114(3) 1 d PG A 2 H64_5 H -0.0106 0.1095 0.3797 0.053 Uiso 0.114(3) 1 d PG A 2 C74_5 C 0.305(2) -0.1329(11) 0.3921(8) 0.044(4) Uiso 0.114(3) 1 d PG A 2 H74_5 H 0.3751 -0.1137 0.3751 0.053 Uiso 0.114(3) 1 d PG A 2 O14_5 O 0.206(2) 0.0948(9) 0.4667(7) 0.044(4) Uiso 0.114(3) 1 d PG A 2 H14_5 H 0.1504 0.1417 0.4608 0.066 Uiso 0.114(3) 1 d PG A 2 O24_5 O 0.311(2) -0.0592(10) 0.4325(7) 0.044(4) Uiso 0.114(3) 1 d PG A 2 O34_5 O 0.312(2) -0.2530(11) 0.4047(8) 0.044(4) Uiso 0.114(3) 1 d PG A 2 H34_5 H 0.2490 -0.2736 0.4148 0.066 Uiso 0.114(3) 1 d PG A 2 O44_5 O 0.376(2) 0.0920(10) 0.5372(7) 0.044(4) Uiso 0.114(3) 1 d PG A 2 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_1 0.0462(10) 0.0689(12) 0.0374(10) -0.0041(8) -0.0102(8) 0.0184(9) O1_1 0.045(7) 0.057(7) 0.027(6) -0.016(5) -0.016(5) 0.019(6) O2_1 0.038(6) 0.043(6) 0.043(7) -0.015(5) -0.013(5) 0.008(5) O3_1 0.029(6) 0.049(7) 0.048(7) -0.001(5) 0.001(5) 0.007(5) O4_1 0.032(5) 0.043(6) 0.035(6) -0.007(5) -0.005(4) 0.024(5) Br1_2 0.0634(11) 0.0470(9) 0.0375(9) -0.0062(8) -0.0021(8) 0.0225(9) O1_2 0.051(7) 0.055(7) 0.037(6) -0.002(6) -0.012(5) 0.021(6) O2_2 0.033(6) 0.040(6) 0.046(7) -0.011(5) -0.008(5) 0.011(5) O3_2 0.043(6) 0.035(6) 0.038(6) -0.001(5) 0.000(5) 0.006(5) O4_2 0.039(6) 0.030(5) 0.034(6) -0.010(4) -0.001(5) 0.003(5) Br1_3 0.0524(11) 0.0678(12) 0.0399(10) -0.0045(9) -0.0130(8) 0.0223(10) O1_3 0.045(7) 0.052(7) 0.053(8) -0.013(6) -0.008(6) 0.021(6) O2_3 0.040(6) 0.047(6) 0.024(6) -0.015(5) -0.002(5) 0.020(5) O3_3 0.030(5) 0.037(6) 0.045(7) -0.004(5) 0.013(5) 0.008(5) O4_3 0.040(7) 0.052(7) 0.047(7) -0.008(6) 0.000(5) 0.009(6) Br1_4 0.0566(10) 0.0547(11) 0.0359(9) -0.0162(8) -0.0055(7) 0.0153(9) O1_4 0.043(6) 0.042(7) 0.044(7) -0.019(5) -0.016(5) 0.017(5) O2_4 0.031(5) 0.042(6) 0.044(7) -0.012(5) -0.020(5) 0.014(5) O3_4 0.028(5) 0.030(5) 0.038(6) 0.009(4) -0.012(4) 0.011(4) O4_4 0.050(7) 0.043(7) 0.039(7) -0.001(5) -0.003(5) 0.014(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 Br1_1 C3_1 1.880(9) . ? B1_1 O1_1 1.353(11) . ? B1_1 O2_1 1.368(11) . ? B1_1 C1_1 1.558(11) . ? C1_1 C6_1 1.394(11) . ? C1_1 C2_1 1.395(11) . ? C2_1 C3_1 1.396(10) . ? C2_1 C7_1 1.492(11) . ? C3_1 C4_1 1.375(6) . ? C4_1 C5_1 1.374(6) . ? C5_1 C6_1 1.395(12) . ? C7_1 O3_1 1.368(10) . ? C7_1 O2_1 1.443(10) . ? Br1_2 C3_2 1.889(9) . ? B1_2 O1_2 1.358(11) . ? B1_2 O2_2 1.370(12) . ? B1_2 C1_2 1.550(11) . ? C1_2 C6_2 1.391(11) . ? C1_2 C2_2 1.401(11) . ? C2_2 C3_2 1.399(10) . ? C2_2 C7_2 1.495(11) . ? C3_2 C4_2 1.376(6) . ? C4_2 C5_2 1.375(6) . ? C5_2 C6_2 1.391(12) . ? C7_2 O3_2 1.368(10) . ? C7_2 O2_2 1.443(11) . ? Br1_3 C3_3 1.893(9) . ? B1_3 O1_3 1.351(11) . ? B1_3 O2_3 1.372(12) . ? B1_3 C1_3 1.551(12) . ? C1_3 C2_3 1.393(11) . ? C1_3 C6_3 1.398(11) . ? C2_3 C3_3 1.394(10) . ? C2_3 C7_3 1.493(11) . ? C3_3 C4_3 1.374(6) . ? C4_3 C5_3 1.374(6) . ? C5_3 C6_3 1.388(12) . ? C7_3 O3_3 1.374(9) . ? C7_3 O2_3 1.452(10) . ? Br1_4 C3_4 1.891(9) . ? B1_4 O1_4 1.353(11) . ? B1_4 O2_4 1.374(12) . ? B1_4 C1_4 1.548(11) . ? C1_4 C6_4 1.394(11) . ? C1_4 C2_4 1.401(11) . ? C2_4 C3_4 1.397(10) . ? C2_4 C7_4 1.506(11) . ? C3_4 C4_4 1.376(6) . ? C4_4 C5_4 1.376(6) . ? C5_4 C6_4 1.395(12) . ? C7_4 O3_4 1.388(9) . ? C7_4 O2_4 1.440(10) . ? Br11_5 C31_5 1.8806 . ? B11_5 O11_5 1.3526 . ? B11_5 O21_5 1.3685 . ? B11_5 C11_5 1.5585 . ? C11_5 C61_5 1.3942 . ? C11_5 C21_5 1.3952 . ? C21_5 C31_5 1.3982 . ? C21_5 C71_5 1.4913 . ? C31_5 C41_5 1.3729 . ? C41_5 C51_5 1.3720 . ? C51_5 C61_5 1.3934 . ? C71_5 O31_5 1.3666 . ? C71_5 O21_5 1.4424 . ? Br12_5 C32_5 1.8893 . ? B12_5 O12_5 1.3573 . ? B12_5 O22_5 1.3703 . ? B12_5 C12_5 1.5511 . ? C12_5 C62_5 1.3907 . ? C12_5 C22_5 1.4013 . ? C22_5 C32_5 1.4009 . ? C22_5 C72_5 1.4945 . ? C32_5 C42_5 1.3745 . ? C42_5 C52_5 1.3734 . ? C52_5 C62_5 1.3903 . ? C72_5 O32_5 1.3666 . ? C72_5 O22_5 1.4440 . ? Br13_5 C33_5 1.8921 . ? B13_5 O13_5 1.3511 . ? B13_5 O23_5 1.3727 . ? B13_5 C13_5 1.5514 . ? C13_5 C23_5 1.3924 . ? C13_5 C63_5 1.3983 . ? C23_5 C33_5 1.3963 . ? C23_5 C73_5 1.4923 . ? C33_5 C43_5 1.3725 . ? C43_5 C53_5 1.3722 . ? C53_5 C63_5 1.3871 . ? C73_5 O33_5 1.3726 . ? C73_5 O23_5 1.4526 . ? Br14_5 C34_5 1.8913 . ? B14_5 O14_5 1.3527 . ? B14_5 O24_5 1.3746 . ? B14_5 C14_5 1.5486 . ? C14_5 C64_5 1.3944 . ? C14_5 C24_5 1.4007 . ? C24_5 C34_5 1.3992 . ? C24_5 C74_5 1.5055 . ? C34_5 C44_5 1.3746 . ? C44_5 C54_5 1.3737 . ? C54_5 C64_5 1.3942 . ? C74_5 O34_5 1.3867 . ? C74_5 O24_5 1.4408 . ? 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_1 B1_1 O2_1 118.9(9) . . ? O1_1 B1_1 C1_1 132.4(9) . . ? O2_1 B1_1 C1_1 108.7(7) . . ? C6_1 C1_1 C2_1 119.6(7) . . ? C6_1 C1_1 B1_1 136.7(8) . . ? C2_1 C1_1 B1_1 103.7(7) . . ? C1_1 C2_1 C3_1 120.8(7) . . ? C1_1 C2_1 C7_1 111.6(7) . . ? C3_1 C2_1 C7_1 127.6(8) . . ? C4_1 C3_1 C2_1 118.3(8) . . ? C4_1 C3_1 Br1_1 119.1(7) . . ? C2_1 C3_1 Br1_1 122.6(6) . . ? C5_1 C4_1 C3_1 122.1(9) . . ? C4_1 C5_1 C6_1 119.8(9) . . ? C1_1 C6_1 C5_1 119.4(9) . . ? O3_1 C7_1 O2_1 110.5(7) . . ? O3_1 C7_1 C2_1 119.3(7) . . ? O2_1 C7_1 C2_1 105.0(7) . . ? B1_1 O2_1 C7_1 111.0(7) . . ? O1_2 B1_2 O2_2 118.9(9) . . ? O1_2 B1_2 C1_2 131.7(9) . . ? O2_2 B1_2 C1_2 109.4(7) . . ? C6_2 C1_2 C2_2 119.9(8) . . ? C6_2 C1_2 B1_2 136.8(8) . . ? C2_2 C1_2 B1_2 103.3(7) . . ? C3_2 C2_2 C1_2 119.8(7) . . ? C3_2 C2_2 C7_2 128.5(8) . . ? C1_2 C2_2 C7_2 111.7(7) . . ? C4_2 C3_2 C2_2 119.2(8) . . ? C4_2 C3_2 Br1_2 119.3(7) . . ? C2_2 C3_2 Br1_2 121.4(6) . . ? C5_2 C4_2 C3_2 121.4(9) . . ? C4_2 C5_2 C6_2 120.0(9) . . ? C1_2 C6_2 C5_2 119.6(9) . . ? O3_2 C7_2 O2_2 109.3(7) . . ? O3_2 C7_2 C2_2 120.1(7) . . ? O2_2 C7_2 C2_2 104.9(7) . . ? B1_2 O2_2 C7_2 110.7(7) . . ? O1_3 B1_3 O2_3 118.8(9) . . ? O1_3 B1_3 C1_3 132.1(9) . . ? O2_3 B1_3 C1_3 109.1(7) . . ? C2_3 C1_3 C6_3 119.4(8) . . ? C2_3 C1_3 B1_3 103.6(7) . . ? C6_3 C1_3 B1_3 137.0(8) . . ? C1_3 C2_3 C3_3 120.4(7) . . ? C1_3 C2_3 C7_3 112.2(7) . . ? C3_3 C2_3 C7_3 127.4(8) . . ? C4_3 C3_3 C2_3 118.9(8) . . ? C4_3 C3_3 Br1_3 119.7(7) . . ? C2_3 C3_3 Br1_3 121.4(6) . . ? C5_3 C4_3 C3_3 121.9(9) . . ? C4_3 C5_3 C6_3 119.6(9) . . ? C5_3 C6_3 C1_3 119.9(9) . . ? O3_3 C7_3 O2_3 108.8(7) . . ? O3_3 C7_3 C2_3 119.5(7) . . ? O2_3 C7_3 C2_3 104.4(7) . . ? B1_3 O2_3 C7_3 110.8(7) . . ? O1_4 B1_4 O2_4 118.2(9) . . ? O1_4 B1_4 C1_4 132.3(9) . . ? O2_4 B1_4 C1_4 109.5(7) . . ? C6_4 C1_4 C2_4 119.4(8) . . ? C6_4 C1_4 B1_4 137.0(8) . . ? C2_4 C1_4 B1_4 103.6(7) . . ? C3_4 C2_4 C1_4 120.4(7) . . ? C3_4 C2_4 C7_4 128.2(7) . . ? C1_4 C2_4 C7_4 111.3(7) . . ? C4_4 C3_4 C2_4 119.2(8) . . ? C4_4 C3_4 Br1_4 119.9(7) . . ? C2_4 C3_4 Br1_4 120.9(6) . . ? C5_4 C4_4 C3_4 121.0(9) . . ? C4_4 C5_4 C6_4 120.6(9) . . ? C1_4 C6_4 C5_4 119.4(9) . . ? O3_4 C7_4 O2_4 109.3(6) . . ? O3_4 C7_4 C2_4 117.1(6) . . ? O2_4 C7_4 C2_4 104.9(7) . . ? B1_4 O2_4 C7_4 110.7(7) . . ? O11_5 B11_5 O21_5 118.9 . . ? O11_5 B11_5 C11_5 132.4 . . ? O21_5 B11_5 C11_5 108.7 . . ? C61_5 C11_5 C21_5 119.5 . . ? C61_5 C11_5 B11_5 136.8 . . ? C21_5 C11_5 B11_5 103.7 . . ? C11_5 C21_5 C31_5 120.7 . . ? C11_5 C21_5 C71_5 111.6 . . ? C31_5 C21_5 C71_5 127.7 . . ? C41_5 C31_5 C21_5 118.2 . . ? C41_5 C31_5 Br11_5 119.3 . . ? C21_5 C31_5 Br11_5 122.5 . . ? C51_5 C41_5 C31_5 122.3 . . ? C41_5 C51_5 C61_5 119.8 . . ? C51_5 C61_5 C11_5 119.5 . . ? O31_5 C71_5 O21_5 110.5 . . ? O31_5 C71_5 C21_5 119.5 . . ? O21_5 C71_5 C21_5 105.1 . . ? B11_5 O21_5 C71_5 110.9 . . ? O12_5 B12_5 O22_5 118.9 . . ? O12_5 B12_5 C12_5 131.7 . . ? O22_5 B12_5 C12_5 109.4 . . ? C62_5 C12_5 C22_5 119.9 . . ? C62_5 C12_5 B12_5 136.8 . . ? C22_5 C12_5 B12_5 103.3 . . ? C32_5 C22_5 C12_5 119.7 . . ? C32_5 C22_5 C72_5 128.5 . . ? C12_5 C22_5 C72_5 111.7 . . ? C42_5 C32_5 C22_5 119.1 . . ? C42_5 C32_5 Br12_5 119.6 . . ? C22_5 C32_5 Br12_5 121.3 . . ? C52_5 C42_5 C32_5 121.6 . . ? C42_5 C52_5 C62_5 120.0 . . ? C52_5 C62_5 C12_5 119.7 . . ? O32_5 C72_5 O22_5 109.3 . . ? O32_5 C72_5 C22_5 120.4 . . ? O22_5 C72_5 C22_5 104.9 . . ? B12_5 O22_5 C72_5 110.6 . . ? O13_5 B13_5 O23_5 118.9 . . ? O13_5 B13_5 C13_5 132.1 . . ? O23_5 B13_5 C13_5 109.0 . . ? C23_5 C13_5 C63_5 119.5 . . ? C23_5 C13_5 B13_5 103.6 . . ? C63_5 C13_5 B13_5 136.9 . . ? C13_5 C23_5 C33_5 120.3 . . ? C13_5 C23_5 C73_5 112.2 . . ? C33_5 C23_5 C73_5 127.4 . . ? C43_5 C33_5 C23_5 118.8 . . ? C43_5 C33_5 Br13_5 120.0 . . ? C23_5 C33_5 Br13_5 121.3 . . ? C53_5 C43_5 C33_5 122.1 . . ? C43_5 C53_5 C63_5 119.5 . . ? C53_5 C63_5 C13_5 119.9 . . ? O33_5 C73_5 O23_5 108.7 . . ? O33_5 C73_5 C23_5 119.7 . . ? O23_5 C73_5 C23_5 104.4 . . ? B13_5 O23_5 C73_5 110.7 . . ? O14_5 B14_5 O24_5 118.2 . . ? O14_5 B14_5 C14_5 132.3 . . ? O24_5 B14_5 C14_5 109.5 . . ? C64_5 C14_5 C24_5 119.5 . . ? C64_5 C14_5 B14_5 137.0 . . ? C24_5 C14_5 B14_5 103.6 . . ? C34_5 C24_5 C14_5 120.3 . . ? C34_5 C24_5 C74_5 128.3 . . ? C14_5 C24_5 C74_5 111.4 . . ? C44_5 C34_5 C24_5 119.1 . . ? C44_5 C34_5 Br14_5 120.2 . . ? C24_5 C34_5 Br14_5 120.7 . . ? C54_5 C44_5 C34_5 121.2 . . ? C44_5 C54_5 C64_5 120.4 . . ? C54_5 C64_5 C14_5 119.4 . . ? O34_5 C74_5 O24_5 109.2 . . ? O34_5 C74_5 C24_5 117.3 . . ? O24_5 C74_5 C24_5 104.9 . . ? B14_5 O24_5 C74_5 110.7 . . ? _refine_diff_density_max 0.764 _refine_diff_density_min -0.782 _refine_diff_density_rms 0.118