Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Holger Bettinger' 'Matthias Filthaus' 'Iris M. Oppel' _publ_contact_author_name 'Holger Bettinger' _publ_contact_author_address ; Lehrstuhl fuer Organische Chemie II Ruhr University Bochum Universitaetsstr. 150 NC4/173 Bochum 44780 GERMANY ; _publ_contact_author_email HOLGER.BETTINGER@RUB.DE _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; Supramolecular structures and spontaneous resolution: the case of ortho substituted phenylboronic acids ; data_p21212 _database_code_depnum_ccdc_archive 'CCDC 670992' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H10 B Br O2' _chemical_formula_weight 300.94 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 orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/2, y+1/2, -z' 'x+1/2, -y+1/2, -z' _cell_length_a 14.4683(9) _cell_length_b 17.0943(11) _cell_length_c 4.9200(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1216.84(12) _cell_formula_units_Z 4 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 4828 _cell_measurement_theta_min 2.8 _cell_measurement_theta_max 30.0 _exptl_crystal_description prism _exptl_crystal_colour pale-yellow _exptl_crystal_size_max 0.456 _exptl_crystal_size_mid 0.219 _exptl_crystal_size_min 0.176 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.643 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 600 _exptl_absorpt_coefficient_mu 3.366 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.43 _exptl_absorpt_correction_T_max 0.56 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.4 Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 108(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 '426 frames in \w and 10 sec ' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9359 _diffrn_reflns_av_R_equivalents 0.0284 _diffrn_reflns_av_sigmaI/netI 0.0406 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 4 _diffrn_reflns_theta_min 2.82 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2786 _reflns_number_gt 2332 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD 32.4, Oxford Diffraction Ltd.' _computing_cell_refinement 'CrysAlis RED 32.4, Oxford Diffraction Ltd.' _computing_data_reduction 'CrysAlis RED 32.4, Oxford Diffraction Ltd.' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXL-97 _computing_publication_material SHELXL-97 _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^)+(0.0255P)^2^+0.0000P] 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 mixed _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 -0.014(8) _refine_ls_number_reflns 2786 _refine_ls_number_parameters 171 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0323 _refine_ls_R_factor_gt 0.0240 _refine_ls_wR_factor_ref 0.0490 _refine_ls_wR_factor_gt 0.0480 _refine_ls_goodness_of_fit_ref 0.955 _refine_ls_restrained_S_all 0.955 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.001 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 0.598153(17) 0.842771(16) 0.94898(5) 0.02963(8) Uani 1 1 d . . . B1 B 0.88437(18) 0.57263(16) 0.7513(5) 0.0159(6) Uani 1 1 d . . . O1 O 0.91865(11) 0.54185(10) 0.5184(3) 0.0267(4) Uani 1 1 d . . . H1 H 0.9062 0.5717 0.3877 0.040 Uiso 1 1 calc R . . O2 O 0.92461(10) 0.54605(9) 0.9833(3) 0.0192(4) Uani 1 1 d D . . H21 H 0.9688(19) 0.5149(19) 0.975(7) 0.011(10) Uiso 0.50 1 d PD . . H22 H 0.919(3) 0.555(3) 1.148(3) 0.012(13) Uiso 0.50 1 d PD . . C01 C 0.80647(14) 0.63715(13) 0.7707(4) 0.0143(5) Uani 1 1 d . . . C02 C 0.73188(14) 0.62588(13) 0.9520(5) 0.0159(4) Uani 1 1 d . . . C03 C 0.71522(15) 0.55204(13) 1.0815(5) 0.0195(5) Uani 1 1 d . . . H03 H 0.7550 0.5093 1.0427 0.023 Uiso 1 1 calc R . . C04 C 0.64427(17) 0.54156(16) 1.2575(5) 0.0273(6) Uani 1 1 d . . . H04 H 0.6340 0.4915 1.3358 0.033 Uiso 1 1 calc R . . C05 C 0.58564(18) 0.60441(15) 1.3251(5) 0.0296(6) Uani 1 1 d . . . H05 H 0.5379 0.5971 1.4551 0.036 Uiso 1 1 calc R . . C06 C 0.59697(17) 0.67546(14) 1.2057(4) 0.0248(6) Uani 1 1 d . . . H06 H 0.5565 0.7171 1.2526 0.030 Uiso 1 1 calc R . . C07 C 0.66861(14) 0.68888(14) 1.0111(4) 0.0186(5) Uani 1 1 d . . . C08 C 0.68108(16) 0.75956(13) 0.8733(4) 0.0187(5) Uani 1 1 d . . . C09 C 0.75039(16) 0.77136(13) 0.6801(4) 0.0176(5) Uani 1 1 d . . . C10 C 0.76085(15) 0.84187(14) 0.5289(4) 0.0236(5) Uani 1 1 d . . . H10 H 0.7184 0.8834 0.5577 0.028 Uiso 1 1 calc R . . C11 C 0.82983(16) 0.85130(16) 0.3450(5) 0.0266(6) Uani 1 1 d . . . H11 H 0.8344 0.8985 0.2438 0.032 Uiso 1 1 calc R . . C12 C 0.89493(19) 0.79074(14) 0.3044(4) 0.0239(5) Uani 1 1 d . . . H12 H 0.9437 0.7979 0.1777 0.029 Uiso 1 1 calc R . . C13 C 0.88868(15) 0.72282(13) 0.4436(4) 0.0204(5) Uani 1 1 d . . . H13 H 0.9340 0.6834 0.4151 0.025 Uiso 1 1 calc R . . C14 C 0.81526(15) 0.70874(14) 0.6334(4) 0.0159(5) Uani 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 0.02525(12) 0.02357(13) 0.04007(14) -0.00789(11) -0.00454(12) 0.01256(11) B1 0.0154(14) 0.0177(14) 0.0147(12) -0.0010(11) 0.0000(10) -0.0011(11) O1 0.0320(10) 0.0313(10) 0.0169(9) -0.0048(7) -0.0004(7) 0.0117(7) O2 0.0211(9) 0.0208(9) 0.0156(10) 0.0024(7) -0.0034(6) 0.0019(6) C01 0.0162(11) 0.0146(13) 0.0120(11) -0.0041(9) -0.0053(9) 0.0005(9) C02 0.0142(10) 0.0185(11) 0.0151(10) -0.0025(10) -0.0059(10) 0.0007(8) C03 0.0169(11) 0.0205(13) 0.0210(12) -0.0014(10) -0.0032(11) 0.0007(9) C04 0.0246(14) 0.0274(16) 0.0301(15) 0.0047(11) 0.0022(11) -0.0008(12) C05 0.0203(14) 0.0368(17) 0.0318(14) 0.0011(11) 0.0044(11) 0.0014(12) C06 0.0154(11) 0.0319(16) 0.0271(12) -0.0086(10) 0.0012(11) 0.0082(12) C07 0.0155(11) 0.0219(12) 0.0184(14) -0.0049(10) -0.0029(9) 0.0009(9) C08 0.0173(11) 0.0161(13) 0.0228(13) -0.0083(9) -0.0067(9) 0.0076(9) C09 0.0198(12) 0.0137(13) 0.0194(12) -0.0020(10) -0.0082(9) 0.0000(10) C10 0.0291(11) 0.0146(11) 0.0273(12) 0.0000(13) -0.0100(10) 0.0040(10) C11 0.0352(14) 0.0190(14) 0.0257(12) 0.0030(12) -0.0090(10) -0.0048(12) C12 0.0253(13) 0.0258(14) 0.0206(12) -0.0016(10) 0.0001(12) -0.0050(13) C13 0.0219(12) 0.0218(12) 0.0177(10) -0.0021(10) -0.0036(11) -0.0009(10) C14 0.0156(12) 0.0183(13) 0.0138(11) -0.0025(9) -0.0056(9) 0.0020(10) _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 C08 1.898(2) . ? B1 O1 1.355(3) . ? B1 O2 1.359(3) . ? B1 C01 1.580(3) . ? C01 C14 1.404(3) . ? C01 C02 1.413(3) . ? C02 C03 1.434(3) . ? C02 C07 1.443(3) . ? C03 C04 1.355(3) . ? C04 C05 1.409(3) . ? C05 C06 1.359(3) . ? C06 C07 1.430(3) . ? C07 C08 1.397(3) . ? C08 C09 1.397(3) . ? C09 C10 1.424(3) . ? C09 C14 1.442(3) . ? C10 C11 1.357(3) . ? C11 C12 1.414(3) . ? C12 C13 1.351(3) . ? C13 C14 1.435(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 115.1(2) . . ? O1 B1 C01 125.7(2) . . ? O2 B1 C01 119.23(19) . . ? C14 C01 C02 119.5(2) . . ? C14 C01 B1 120.99(19) . . ? C02 C01 B1 119.18(19) . . ? C01 C02 C03 121.9(2) . . ? C01 C02 C07 120.6(2) . . ? C03 C02 C07 117.4(2) . . ? C04 C03 C02 121.8(2) . . ? C03 C04 C05 120.4(2) . . ? C06 C05 C04 120.5(2) . . ? C05 C06 C07 121.4(2) . . ? C08 C07 C06 123.9(2) . . ? C08 C07 C02 117.8(2) . . ? C06 C07 C02 118.4(2) . . ? C09 C08 C07 123.2(2) . . ? C09 C08 Br1 118.64(17) . . ? C07 C08 Br1 118.13(17) . . ? C08 C09 C10 123.6(2) . . ? C08 C09 C14 118.0(2) . . ? C10 C09 C14 118.4(2) . . ? C11 C10 C09 121.8(2) . . ? C10 C11 C12 119.8(2) . . ? C13 C12 C11 120.9(2) . . ? C12 C13 C14 121.6(2) . . ? C01 C14 C13 121.8(2) . . ? C01 C14 C09 120.8(2) . . ? C13 C14 C09 117.5(2) . . ? 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 O1 B1 C01 C14 -54.7(3) . . . . ? O2 B1 C01 C14 122.8(2) . . . . ? O1 B1 C01 C02 132.2(2) . . . . ? O2 B1 C01 C02 -50.3(3) . . . . ? C14 C01 C02 C03 175.0(2) . . . . ? B1 C01 C02 C03 -11.8(3) . . . . ? C14 C01 C02 C07 -4.3(3) . . . . ? B1 C01 C02 C07 168.97(19) . . . . ? C01 C02 C03 C04 179.3(2) . . . . ? C07 C02 C03 C04 -1.4(3) . . . . ? C02 C03 C04 C05 -1.8(4) . . . . ? C03 C04 C05 C06 2.9(4) . . . . ? C04 C05 C06 C07 -0.6(4) . . . . ? C05 C06 C07 C08 177.1(2) . . . . ? C05 C06 C07 C02 -2.7(3) . . . . ? C01 C02 C07 C08 3.1(3) . . . . ? C03 C02 C07 C08 -176.2(2) . . . . ? C01 C02 C07 C06 -177.1(2) . . . . ? C03 C02 C07 C06 3.6(3) . . . . ? C06 C07 C08 C09 -178.8(2) . . . . ? C02 C07 C08 C09 1.0(3) . . . . ? C06 C07 C08 Br1 0.0(3) . . . . ? C02 C07 C08 Br1 179.91(15) . . . . ? C07 C08 C09 C10 176.8(2) . . . . ? Br1 C08 C09 C10 -2.1(3) . . . . ? C07 C08 C09 C14 -3.7(3) . . . . ? Br1 C08 C09 C14 177.40(16) . . . . ? C08 C09 C10 C11 179.3(2) . . . . ? C14 C09 C10 C11 -0.2(3) . . . . ? C09 C10 C11 C12 -1.5(3) . . . . ? C10 C11 C12 C13 1.0(3) . . . . ? C11 C12 C13 C14 1.2(4) . . . . ? C02 C01 C14 C13 -178.9(2) . . . . ? B1 C01 C14 C13 8.0(3) . . . . ? C02 C01 C14 C09 1.5(3) . . . . ? B1 C01 C14 C09 -171.64(19) . . . . ? C12 C13 C14 C01 177.5(2) . . . . ? C12 C13 C14 C09 -2.8(3) . . . . ? C08 C09 C14 C01 2.5(3) . . . . ? C10 C09 C14 C01 -178.1(2) . . . . ? C08 C09 C14 C13 -177.2(2) . . . . ? C10 C09 C14 C13 2.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.446 _refine_diff_density_min -0.302 _refine_diff_density_rms 0.061 # Attachment '11a.cif' data_c2c _database_code_depnum_ccdc_archive 'CCDC 670993' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H15 B O2' _chemical_formula_weight 250.09 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/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 31.502(3) _cell_length_b 7.6126(6) _cell_length_c 12.1156(7) _cell_angle_alpha 90.00 _cell_angle_beta 110.098(12) _cell_angle_gamma 90.00 _cell_volume 2728.5(4) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7016 _cell_measurement_theta_min 2.7 _cell_measurement_theta_max 30.0 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.53 _exptl_crystal_size_min 0.47 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.218 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1056 _exptl_absorpt_coefficient_mu 0.078 _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 294(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 'Sapphire2-CCD, Oxford Diffraction' _diffrn_measurement_method '887 images at 1.0 deg in \w and 15 sec' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16883 _diffrn_reflns_av_R_equivalents 0.0795 _diffrn_reflns_av_sigmaI/netI 0.0390 _diffrn_reflns_limit_h_min -37 _diffrn_reflns_limit_h_max 37 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.76 _diffrn_reflns_theta_max 25.23 _reflns_number_total 2464 _reflns_number_gt 1702 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD 1.171.29, Oxford Diffraction' _computing_cell_refinement 'CrysAlis RED 1.171.29, Oxford Diffraction' _computing_data_reduction 'CrysAlis RED 1.171.29, Oxford Diffraction' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXL-97 _computing_publication_material SHELXL-97 _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^)+(0.0931P)^2^+0.9839P] 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_extinction_coef ? _refine_ls_number_reflns 2464 _refine_ls_number_parameters 185 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0770 _refine_ls_R_factor_gt 0.0530 _refine_ls_wR_factor_ref 0.1597 _refine_ls_wR_factor_gt 0.1391 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.001 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 C1 C 0.17083(7) 0.7303(3) 0.40279(17) 0.0601(5) Uani 1 1 d . . . H1 H 0.1960 0.7952 0.4044 0.072 Uiso 1 1 calc R . . C2 C 0.17297(8) 0.6308(3) 0.49721(19) 0.0732(6) Uani 1 1 d . . . H2 H 0.1993 0.6287 0.5625 0.088 Uiso 1 1 calc R . . C3 C 0.13516(9) 0.5302(3) 0.4967(2) 0.0754(6) Uani 1 1 d . . . H3 H 0.1368 0.4623 0.5618 0.090 Uiso 1 1 calc R . . C4A C 0.09300(6) 0.6344(2) 0.30124(16) 0.0504(5) Uani 1 1 d . . . C4 C 0.09688(8) 0.5320(3) 0.40270(19) 0.0656(6) Uani 1 1 d . . . H4 H 0.0724 0.4649 0.4039 0.079 Uiso 1 1 calc R . . C5 C 0.01085(6) 0.7403(3) 0.00153(18) 0.0588(5) Uani 1 1 d . . . H5 H -0.0139 0.6725 0.0000 0.071 Uiso 1 1 calc R . . C6 C 0.00847(7) 0.8393(3) -0.09280(19) 0.0640(6) Uani 1 1 d . . . H6 H -0.0177 0.8380 -0.1588 0.077 Uiso 1 1 calc R . . C7 C 0.04553(7) 0.9451(3) -0.09178(17) 0.0610(5) Uani 1 1 d . . . H7 H 0.0435 1.0141 -0.1568 0.073 Uiso 1 1 calc R . . C8A C 0.08861(6) 0.8433(2) 0.10487(15) 0.0449(4) Uani 1 1 d . . . C8 C 0.08402(6) 0.9465(2) 0.00324(16) 0.0530(5) Uani 1 1 d . . . H8 H 0.1080 1.0167 0.0021 0.064 Uiso 1 1 calc R . . C9 C 0.12857(6) 0.8420(2) 0.20303(15) 0.0451(4) Uani 1 1 d . . . C9A C 0.13112(6) 0.7382(2) 0.30122(15) 0.0476(4) Uani 1 1 d . . . B9 B 0.17117(7) 0.9520(3) 0.20327(17) 0.0483(5) Uani 1 1 d . A . C10A C 0.05072(6) 0.7378(2) 0.10371(16) 0.0480(4) Uani 1 1 d . . . C10 C 0.05413(6) 0.6364(2) 0.20207(17) 0.0540(5) Uani 1 1 d . . . H10 H 0.0296 0.5679 0.2014 0.065 Uiso 1 1 calc R . . O91 O 0.20039(5) 0.87247(18) 0.16065(14) 0.0696(5) Uani 1 1 d . . . C91 C 0.24036(7) 0.9591(3) 0.1570(2) 0.0831(7) Uani 1 1 d . . . H91A H 0.2382 1.0828 0.1698 0.125 Uiso 1 1 calc R . . H91B H 0.2432 0.9407 0.0815 0.125 Uiso 1 1 calc R . . H91C H 0.2664 0.9120 0.2172 0.125 Uiso 1 1 calc R . . O92 O 0.17982(5) 1.11714(18) 0.24456(14) 0.0729(5) Uani 1 1 d . . . C92 C 0.1507(5) 1.198(2) 0.2965(15) 0.114(5) Uani 0.59(4) 1 d P A 1 H92A H 0.1207 1.1521 0.2612 0.172 Uiso 0.59(4) 1 calc PR A 1 H92B H 0.1504 1.3226 0.2840 0.172 Uiso 0.59(4) 1 calc PR A 1 H92C H 0.1614 1.1739 0.3793 0.172 Uiso 0.59(4) 1 calc PR A 1 C92' C 0.1489(5) 1.228(3) 0.280(2) 0.098(5) Uani 0.41(4) 1 d P A 2 H92D H 0.1264 1.2760 0.2117 0.146 Uiso 0.41(4) 1 calc PR A 2 H92E H 0.1655 1.3220 0.3289 0.146 Uiso 0.41(4) 1 calc PR A 2 H92F H 0.1345 1.1589 0.3235 0.146 Uiso 0.41(4) 1 calc PR 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 C1 0.0693(12) 0.0540(11) 0.0587(11) -0.0032(9) 0.0241(10) -0.0084(9) C2 0.0878(16) 0.0697(14) 0.0583(13) 0.0035(10) 0.0202(11) -0.0026(12) C3 0.1099(18) 0.0616(13) 0.0630(13) 0.0073(10) 0.0404(14) -0.0074(13) C4A 0.0650(11) 0.0383(9) 0.0602(11) -0.0059(8) 0.0373(9) -0.0046(8) C4 0.0867(15) 0.0535(12) 0.0702(14) 0.0001(10) 0.0444(12) -0.0107(10) C5 0.0497(11) 0.0536(11) 0.0753(13) -0.0124(10) 0.0244(10) -0.0060(8) C6 0.0576(12) 0.0620(12) 0.0656(13) -0.0089(10) 0.0123(10) 0.0040(9) C7 0.0699(12) 0.0565(12) 0.0567(11) 0.0019(9) 0.0218(10) 0.0024(10) C8A 0.0494(10) 0.0386(9) 0.0532(10) -0.0072(7) 0.0259(8) -0.0009(7) C8 0.0587(11) 0.0469(10) 0.0582(11) -0.0024(8) 0.0264(9) -0.0032(8) C9 0.0509(10) 0.0375(9) 0.0532(10) -0.0059(7) 0.0262(8) -0.0014(7) C9A 0.0581(11) 0.0388(9) 0.0523(10) -0.0061(7) 0.0274(8) -0.0029(7) B9 0.0498(11) 0.0487(11) 0.0492(11) 0.0041(9) 0.0208(9) 0.0008(9) C10A 0.0497(10) 0.0405(9) 0.0615(11) -0.0109(8) 0.0288(9) -0.0031(7) C10 0.0559(11) 0.0447(10) 0.0727(13) -0.0102(9) 0.0365(10) -0.0123(8) O91 0.0623(9) 0.0605(9) 0.1010(11) 0.0038(7) 0.0474(8) 0.0025(6) C91 0.0561(12) 0.0894(17) 0.1196(19) 0.0277(14) 0.0504(13) 0.0127(11) O92 0.0739(10) 0.0585(9) 0.1038(11) -0.0219(8) 0.0529(9) -0.0227(7) C92 0.168(12) 0.054(5) 0.168(8) -0.053(6) 0.118(8) -0.041(5) C92' 0.089(7) 0.058(8) 0.191(14) -0.020(7) 0.105(9) -0.014(5) _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 C1 C2 1.354(3) . ? C1 C9A 1.423(3) . ? C2 C3 1.414(3) . ? C3 C4 1.344(3) . ? C4A C10 1.390(3) . ? C4A C4 1.425(3) . ? C4A C9A 1.438(2) . ? C5 C6 1.349(3) . ? C5 C10A 1.429(3) . ? C6 C7 1.415(3) . ? C7 C8 1.355(3) . ? C8A C9 1.404(2) . ? C8A C8 1.426(2) . ? C8A C10A 1.435(2) . ? C9 C9A 1.408(2) . ? C9 B9 1.581(3) . ? B9 O91 1.344(2) . ? B9 O92 1.346(2) . ? C10A C10 1.393(3) . ? O91 C91 1.436(2) . ? O92 C92 1.418(11) . ? O92 C92' 1.462(15) . ? 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 C2 C1 C9A 121.88(19) . . ? C1 C2 C3 120.1(2) . . ? C4 C3 C2 120.46(19) . . ? C10 C4A C4 122.75(17) . . ? C10 C4A C9A 118.78(16) . . ? C4 C4A C9A 118.47(18) . . ? C3 C4 C4A 121.51(19) . . ? C6 C5 C10A 121.17(18) . . ? C5 C6 C7 120.33(18) . . ? C8 C7 C6 120.45(18) . . ? C9 C8A C8 122.06(15) . . ? C9 C8A C10A 120.36(15) . . ? C8 C8A C10A 117.58(16) . . ? C7 C8 C8A 121.66(17) . . ? C8A C9 C9A 119.60(15) . . ? C8A C9 B9 120.77(15) . . ? C9A C9 B9 119.61(16) . . ? C9 C9A C1 122.17(16) . . ? C9 C9A C4A 120.26(16) . . ? C1 C9A C4A 117.56(16) . . ? O91 B9 O92 119.04(17) . . ? O91 B9 C9 117.00(16) . . ? O92 B9 C9 123.96(16) . . ? C10 C10A C5 122.35(16) . . ? C10 C10A C8A 118.85(16) . . ? C5 C10A C8A 118.80(16) . . ? C4A C10 C10A 122.14(16) . . ? B9 O91 C91 121.91(17) . . ? B9 O92 C92 119.4(7) . . ? B9 O92 C92' 125.4(8) . . ? C92 O92 C92' 11.6(17) . . ? 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 C9A C1 C2 C3 0.3(3) . . . . ? C1 C2 C3 C4 0.1(3) . . . . ? C2 C3 C4 C4A -0.1(3) . . . . ? C10 C4A C4 C3 178.87(19) . . . . ? C9A C4A C4 C3 -0.4(3) . . . . ? C10A C5 C6 C7 -0.8(3) . . . . ? C5 C6 C7 C8 0.8(3) . . . . ? C6 C7 C8 C8A -0.2(3) . . . . ? C9 C8A C8 C7 179.06(16) . . . . ? C10A C8A C8 C7 -0.5(2) . . . . ? C8 C8A C9 C9A 179.69(15) . . . . ? C10A C8A C9 C9A -0.8(2) . . . . ? C8 C8A C9 B9 -1.9(2) . . . . ? C10A C8A C9 B9 177.59(15) . . . . ? C8A C9 C9A C1 179.41(15) . . . . ? B9 C9 C9A C1 1.0(2) . . . . ? C8A C9 C9A C4A -0.2(2) . . . . ? B9 C9 C9A C4A -178.58(15) . . . . ? C2 C1 C9A C9 179.64(18) . . . . ? C2 C1 C9A C4A -0.8(3) . . . . ? C10 C4A C9A C9 1.1(2) . . . . ? C4 C4A C9A C9 -179.60(15) . . . . ? C10 C4A C9A C1 -178.51(15) . . . . ? C4 C4A C9A C1 0.8(2) . . . . ? C8A C9 B9 O91 -88.4(2) . . . . ? C9A C9 B9 O91 90.0(2) . . . . ? C8A C9 B9 O92 92.5(2) . . . . ? C9A C9 B9 O92 -89.1(2) . . . . ? C6 C5 C10A C10 -179.78(17) . . . . ? C6 C5 C10A C8A 0.1(3) . . . . ? C9 C8A C10A C10 0.9(2) . . . . ? C8 C8A C10A C10 -179.62(15) . . . . ? C9 C8A C10A C5 -179.01(14) . . . . ? C8 C8A C10A C5 0.5(2) . . . . ? C4 C4A C10 C10A 179.66(17) . . . . ? C9A C4A C10 C10A -1.1(2) . . . . ? C5 C10A C10 C4A 179.96(16) . . . . ? C8A C10A C10 C4A 0.1(2) . . . . ? O92 B9 O91 C91 -0.5(3) . . . . ? C9 B9 O91 C91 -179.71(17) . . . . ? O91 B9 O92 C92 -176.0(10) . . . . ? C9 B9 O92 C92 3.1(10) . . . . ? O91 B9 O92 C92' 172.2(14) . . . . ? C9 B9 O92 C92' -8.7(14) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.23 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.208 _refine_diff_density_min -0.206 _refine_diff_density_rms 0.059 # Attachment '7.cif' data_bettinger4 _database_code_depnum_ccdc_archive 'CCDC 670994' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H6 B Br O2' _chemical_formula_weight 200.83 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 4.9570(8) _cell_length_b 7.0560(10) _cell_length_c 10.7572(17) _cell_angle_alpha 95.766(12) _cell_angle_beta 92.219(13) _cell_angle_gamma 96.613(13) _cell_volume 371.37(10) _cell_formula_units_Z 2 _cell_measurement_temperature 108(2) _cell_measurement_reflns_used 2042 _cell_measurement_theta_min 2.92 _cell_measurement_theta_max 30.00 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.304 _exptl_crystal_size_mid 0.288 _exptl_crystal_size_min 0.270 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.796 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 196 _exptl_absorpt_coefficient_mu 5.463 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.192 _exptl_absorpt_correction_T_max 0.227 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.2 (release 20-01-2006 CrysAlis171 .NET) (compiled Jan 20 2006,12:36:28) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 108(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 'Sapphire2-CCD, Oxford Diffraction' _diffrn_measurement_method '409 images at 1.0 deg in \w and 15 sec' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2727 _diffrn_reflns_av_R_equivalents 0.0202 _diffrn_reflns_av_sigmaI/netI 0.0238 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.32 _diffrn_reflns_theta_max 27.49 _reflns_number_total 1661 _reflns_number_gt 1527 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD 1.171.29, Oxford Diffraction' _computing_cell_refinement 'CrysAlis RED 1.171.29, Oxford Diffraction' _computing_data_reduction 'CrysAlis RED 1.171.29, Oxford Diffraction' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXL-97 _computing_publication_material SHELXL-97 _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^)+(0.0410P)^2^+0.0000P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1661 _refine_ls_number_parameters 99 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0270 _refine_ls_R_factor_gt 0.0241 _refine_ls_wR_factor_ref 0.0595 _refine_ls_wR_factor_gt 0.0589 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.031 _refine_ls_shift/su_mean 0.004 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 0.41537(4) 0.30765(3) 0.870301(18) 0.02316(9) Uani 1 1 d . . . C1 C 0.1605(4) 0.0918(3) 0.80355(19) 0.0161(4) Uani 1 1 d . . . C2 C -0.0183(4) 0.1070(3) 0.70046(18) 0.0144(4) Uani 1 1 d . . . B2 B -0.0146(5) 0.2808(3) 0.6180(2) 0.0144(4) Uani 1 1 d . . . C3 C -0.2160(4) -0.0528(3) 0.6669(2) 0.0195(4) Uani 1 1 d . . . H3 H -0.3441 -0.0481 0.5996 0.023 Uiso 1 1 calc R . . C4 C -0.2289(5) -0.2180(3) 0.7296(2) 0.0249(5) Uani 1 1 d . . . H4 H -0.3646 -0.3228 0.7049 0.030 Uiso 1 1 calc R . . C5 C -0.0422(5) -0.2284(3) 0.8283(2) 0.0246(5) Uani 1 1 d . . . H5 H -0.0480 -0.3416 0.8696 0.029 Uiso 1 1 calc R . . C6 C 0.1532(5) -0.0724(3) 0.8666(2) 0.0231(4) Uani 1 1 d . . . H6 H 0.2794 -0.0779 0.9345 0.028 Uiso 1 1 calc R . . O21 O -0.2573(3) 0.3195(2) 0.56739(14) 0.0197(3) Uani 1 1 d D . . H21 H -0.237(6) 0.399(3) 0.518(2) 0.041(9) Uiso 1 1 d D . . O22 O 0.2153(3) 0.3906(2) 0.58861(14) 0.0178(3) Uani 1 1 d D . . H22 H 0.356(3) 0.350(4) 0.607(3) 0.034(8) Uiso 1 1 d 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 0.02340(13) 0.02668(13) 0.01786(13) 0.00390(8) -0.00536(8) -0.00275(8) C1 0.0145(9) 0.0180(9) 0.0157(9) 0.0019(7) 0.0007(7) 0.0021(7) C2 0.0139(9) 0.0167(9) 0.0138(9) 0.0029(7) 0.0028(7) 0.0052(7) B2 0.0136(10) 0.0175(10) 0.0128(10) 0.0014(8) 0.0023(8) 0.0040(8) C3 0.0180(11) 0.0198(10) 0.0202(10) 0.0019(8) -0.0016(8) 0.0016(8) C4 0.0280(12) 0.0165(10) 0.0291(12) 0.0010(8) 0.0033(9) -0.0009(8) C5 0.0335(13) 0.0175(9) 0.0251(11) 0.0087(8) 0.0067(9) 0.0057(9) C6 0.0259(12) 0.0260(11) 0.0195(10) 0.0080(8) -0.0006(8) 0.0087(9) O21 0.0123(7) 0.0246(7) 0.0244(8) 0.0126(6) 0.0011(6) 0.0033(6) O22 0.0112(7) 0.0227(7) 0.0214(7) 0.0095(6) 0.0003(6) 0.0039(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 C1 1.923(2) . ? C1 C6 1.398(3) . ? C1 C2 1.413(3) . ? C2 C3 1.414(3) . ? C2 B2 1.583(3) . ? B2 O21 1.368(3) . ? B2 O22 1.369(3) . ? C3 C4 1.401(3) . ? C4 C5 1.394(3) . ? C5 C6 1.397(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 C6 C1 C2 123.03(19) . . ? C6 C1 Br1 116.55(16) . . ? C2 C1 Br1 120.32(15) . . ? C1 C2 C3 115.77(18) . . ? C1 C2 B2 126.83(18) . . ? C3 C2 B2 117.38(18) . . ? O21 B2 O22 117.17(18) . . ? O21 B2 C2 117.96(18) . . ? O22 B2 C2 124.81(18) . . ? C4 C3 C2 122.1(2) . . ? C5 C4 C3 119.9(2) . . ? C4 C5 C6 120.0(2) . . ? C1 C6 C5 119.1(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 2.5(3) . . . . ? Br1 C1 C2 C3 -173.72(14) . . . . ? C6 C1 C2 B2 -175.92(19) . . . . ? Br1 C1 C2 B2 7.9(3) . . . . ? C1 C2 B2 O21 -148.4(2) . . . . ? C3 C2 B2 O21 33.2(3) . . . . ? C1 C2 B2 O22 34.7(3) . . . . ? C3 C2 B2 O22 -143.7(2) . . . . ? C1 C2 C3 C4 -1.7(3) . . . . ? B2 C2 C3 C4 176.84(19) . . . . ? C2 C3 C4 C5 -0.2(3) . . . . ? C3 C4 C5 C6 1.6(3) . . . . ? C2 C1 C6 C5 -1.2(3) . . . . ? Br1 C1 C6 C5 175.07(16) . . . . ? C4 C5 C6 C1 -0.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.640 _refine_diff_density_min -0.360 _refine_diff_density_rms 0.092 # Attachment '8.cif' data_bettinger3 _database_code_depnum_ccdc_archive 'CCDC 670995' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H11 B O2' _chemical_formula_weight 198.02 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.2637(9) _cell_length_b 9.2893(8) _cell_length_c 14.5479(19) _cell_angle_alpha 98.514(9) _cell_angle_beta 104.995(10) _cell_angle_gamma 99.904(9) _cell_volume 1040.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 108(2) _cell_measurement_reflns_used 1613 _cell_measurement_theta_min 2.94 _cell_measurement_theta_max 30.00 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.579 _exptl_crystal_size_mid 0.172 _exptl_crystal_size_min 0.111 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.264 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 416 _exptl_absorpt_coefficient_mu 0.083 _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 108(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 'Sapphire2-CCD, Oxford Diffraction' _diffrn_measurement_method '409 images at 1.0 deg in \w and 25 sec' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5955 _diffrn_reflns_av_R_equivalents 0.0735 _diffrn_reflns_av_sigmaI/netI 0.1022 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.95 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3523 _reflns_number_gt 1895 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD 1.171.29, Oxford Diffraction' _computing_cell_refinement 'CrysAlis RED 1.171.29, Oxford Diffraction' _computing_data_reduction 'CrysAlis RED 1.171.29, Oxford Diffraction' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXL-97 _computing_publication_material SHELXL-97 _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^)+(0.0878P)^2^+0.0000P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3523 _refine_ls_number_parameters 287 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.1072 _refine_ls_R_factor_gt 0.0615 _refine_ls_wR_factor_ref 0.1590 _refine_ls_wR_factor_gt 0.1427 _refine_ls_goodness_of_fit_ref 0.863 _refine_ls_restrained_S_all 0.863 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.001 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 0.2654(5) 0.4161(4) 0.3940(2) 0.0282(8) Uani 1 1 d . . . O11 O 0.2855(3) 0.5528(2) 0.45028(16) 0.0330(6) Uani 1 1 d D . . H11 H 0.382(2) 0.581(4) 0.489(2) 0.081(16) Uiso 1 1 d D . . O12 O 0.4073(3) 0.3546(2) 0.40521(15) 0.0295(5) Uani 1 1 d D . . H12 H 0.384(5) 0.2677(17) 0.375(2) 0.056(12) Uiso 1 1 d D . . C11 C 0.0492(4) 0.2645(3) 0.2286(2) 0.0318(8) Uani 1 1 d . . . C12 C 0.0838(4) 0.3336(3) 0.3266(2) 0.0300(7) Uani 1 1 d . . . C13 C -0.0510(4) 0.3198(3) 0.3698(3) 0.0380(8) Uani 1 1 d . . . H13 H -0.0294 0.3662 0.4358 0.046 Uiso 1 1 calc R . . C14 C -0.2151(4) 0.2392(4) 0.3170(3) 0.0494(10) Uani 1 1 d . . . H14 H -0.3053 0.2307 0.3466 0.059 Uiso 1 1 calc R . . C15 C -0.2455(5) 0.1723(4) 0.2219(3) 0.0542(11) Uani 1 1 d . . . H15 H -0.3574 0.1168 0.1857 0.065 Uiso 1 1 calc R . . C16 C -0.1163(5) 0.1843(4) 0.1784(3) 0.0472(9) Uani 1 1 d . . . H16 H -0.1405 0.1366 0.1124 0.057 Uiso 1 1 calc R . . C11' C 0.1805(4) 0.2829(3) 0.1770(2) 0.0311(7) Uani 1 1 d . . . C12' C 0.2030(4) 0.1618(4) 0.1151(2) 0.0435(9) Uani 1 1 d . . . H12' H 0.1360 0.0649 0.1086 0.052 Uiso 1 1 calc R . . C13' C 0.3212(5) 0.1814(4) 0.0634(3) 0.0516(10) Uani 1 1 d . . . H13' H 0.3352 0.0981 0.0221 0.062 Uiso 1 1 calc R . . C14' C 0.4184(5) 0.3210(4) 0.0716(3) 0.0512(10) Uani 1 1 d . . . H14' H 0.4980 0.3344 0.0351 0.061 Uiso 1 1 calc R . . C15' C 0.4003(4) 0.4417(4) 0.1328(2) 0.0394(8) Uani 1 1 d . . . H15' H 0.4690 0.5379 0.1392 0.047 Uiso 1 1 calc R . . C16' C 0.2828(4) 0.4232(3) 0.1846(2) 0.0324(7) Uani 1 1 d . . . H16' H 0.2711 0.5072 0.2263 0.039 Uiso 1 1 calc R . . B2 B 0.3324(4) 0.9181(3) 0.3621(3) 0.0240(8) Uani 1 1 d . . . O21 O 0.3323(3) 0.8513(2) 0.43910(14) 0.0282(5) Uani 1 1 d D . . H21 H 0.293(5) 0.7606(13) 0.427(3) 0.062(12) Uiso 1 1 d D . . O22 O 0.4320(3) 1.0593(2) 0.38064(15) 0.0285(5) Uani 1 1 d D . . H22 H 0.498(3) 1.082(3) 0.4363(11) 0.037(10) Uiso 1 1 d D . . C21 C 0.0621(4) 0.7662(3) 0.2188(2) 0.0274(7) Uani 1 1 d . . . C22 C 0.2359(4) 0.8430(3) 0.2535(2) 0.0267(7) Uani 1 1 d . . . C23 C 0.3341(4) 0.8458(3) 0.1883(2) 0.0314(7) Uani 1 1 d . . . H23 H 0.4505 0.8991 0.2108 0.038 Uiso 1 1 calc R . . C24 C 0.2667(5) 0.7736(3) 0.0924(2) 0.0372(8) Uani 1 1 d . . . H24 H 0.3361 0.7761 0.0495 0.045 Uiso 1 1 calc R . . C25 C 0.0976(5) 0.6980(3) 0.0596(2) 0.0380(8) Uani 1 1 d . . . H25 H 0.0496 0.6482 -0.0065 0.046 Uiso 1 1 calc R . . C26 C -0.0036(4) 0.6939(3) 0.1224(2) 0.0338(8) Uani 1 1 d . . . H26 H -0.1199 0.6406 0.0987 0.041 Uiso 1 1 calc R . . C21' C -0.0516(3) 0.7657(3) 0.2826(2) 0.0253(7) Uani 1 1 d . . . C22' C -0.0579(4) 0.8991(3) 0.3390(2) 0.0309(7) Uani 1 1 d . . . H22' H 0.0130 0.9904 0.3377 0.037 Uiso 1 1 calc R . . C23' C -0.1679(4) 0.8983(4) 0.3970(2) 0.0342(8) Uani 1 1 d . . . H23' H -0.1717 0.9891 0.4354 0.041 Uiso 1 1 calc R . . C24' C -0.2713(4) 0.7664(4) 0.3989(2) 0.0420(9) Uani 1 1 d . . . H24' H -0.3463 0.7664 0.4386 0.050 Uiso 1 1 calc R . . C25' C -0.2664(4) 0.6344(4) 0.3436(2) 0.0409(9) Uani 1 1 d . . . H25' H -0.3372 0.5434 0.3456 0.049 Uiso 1 1 calc R . . C26' C -0.1579(4) 0.6346(3) 0.2851(2) 0.0354(8) Uani 1 1 d . . . H26' H -0.1565 0.5435 0.2461 0.042 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 B1 0.035(2) 0.0213(18) 0.031(2) 0.0080(15) 0.0138(17) 0.0057(16) O11 0.0283(14) 0.0204(11) 0.0445(14) 0.0005(10) 0.0027(11) 0.0074(10) O12 0.0263(12) 0.0185(11) 0.0374(13) -0.0021(9) 0.0022(10) 0.0058(10) C11 0.0262(18) 0.0174(15) 0.043(2) 0.0082(14) -0.0039(15) 0.0014(14) C12 0.0249(18) 0.0197(15) 0.045(2) 0.0083(14) 0.0071(15) 0.0064(14) C13 0.033(2) 0.0265(17) 0.060(2) 0.0154(16) 0.0173(17) 0.0092(15) C14 0.027(2) 0.042(2) 0.084(3) 0.030(2) 0.017(2) 0.0069(17) C15 0.025(2) 0.047(2) 0.078(3) 0.028(2) -0.006(2) -0.0070(17) C16 0.039(2) 0.0317(19) 0.055(2) 0.0113(17) -0.0070(19) -0.0044(17) C11' 0.0300(18) 0.0223(16) 0.0328(18) 0.0032(13) -0.0034(14) 0.0053(14) C12' 0.046(2) 0.0318(19) 0.042(2) 0.0001(15) -0.0062(17) 0.0165(17) C13' 0.061(3) 0.052(2) 0.041(2) -0.0006(18) 0.0067(19) 0.033(2) C14' 0.051(2) 0.062(3) 0.047(2) 0.0097(19) 0.0141(19) 0.030(2) C15' 0.037(2) 0.0398(19) 0.044(2) 0.0101(16) 0.0123(17) 0.0121(16) C16' 0.0341(19) 0.0277(17) 0.0325(18) 0.0033(13) 0.0037(15) 0.0104(15) B2 0.0156(17) 0.0158(17) 0.041(2) 0.0020(15) 0.0102(15) 0.0043(14) O21 0.0260(12) 0.0184(11) 0.0346(12) 0.0015(9) 0.0033(10) 0.0018(10) O22 0.0246(12) 0.0196(11) 0.0354(13) 0.0014(9) 0.0019(11) 0.0032(9) C21 0.0286(18) 0.0171(15) 0.0333(18) 0.0033(13) 0.0033(14) 0.0067(13) C22 0.0252(17) 0.0173(15) 0.0359(18) 0.0031(13) 0.0063(14) 0.0064(13) C23 0.0300(18) 0.0236(16) 0.0411(19) 0.0046(14) 0.0111(15) 0.0078(14) C24 0.047(2) 0.0360(18) 0.0348(19) 0.0078(15) 0.0158(16) 0.0181(17) C25 0.054(2) 0.0315(18) 0.0261(17) 0.0017(14) 0.0055(16) 0.0163(17) C26 0.0310(18) 0.0252(17) 0.0373(19) 0.0022(14) -0.0008(15) 0.0048(14) C21' 0.0181(16) 0.0240(16) 0.0291(16) 0.0038(12) 0.0001(13) 0.0040(13) C22' 0.0262(17) 0.0269(17) 0.0380(19) 0.0064(14) 0.0056(15) 0.0080(14) C23' 0.0295(18) 0.0359(18) 0.0389(19) 0.0075(15) 0.0095(15) 0.0127(15) C24' 0.0300(19) 0.056(2) 0.050(2) 0.0229(18) 0.0170(16) 0.0175(18) C25' 0.032(2) 0.039(2) 0.053(2) 0.0178(17) 0.0109(17) 0.0044(16) C26' 0.0303(19) 0.0262(17) 0.0434(19) 0.0044(14) 0.0029(16) 0.0042(15) _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 O11 1.364(4) . ? B1 O12 1.374(4) . ? B1 C12 1.556(5) . ? C11 C16 1.389(4) . ? C11 C12 1.408(4) . ? C11 C11' 1.472(4) . ? C12 C13 1.410(4) . ? C13 C14 1.389(5) . ? C14 C15 1.369(5) . ? C15 C16 1.373(5) . ? C11' C16' 1.397(4) . ? C11' C12' 1.403(4) . ? C12' C13' 1.383(5) . ? C13' C14' 1.374(5) . ? C14' C15' 1.380(4) . ? C15' C16' 1.379(4) . ? B2 O21 1.359(4) . ? B2 O22 1.371(4) . ? B2 C22 1.564(4) . ? C21 C26 1.383(4) . ? C21 C22 1.412(4) . ? C21 C21' 1.483(4) . ? C22 C23 1.398(4) . ? C23 C24 1.378(4) . ? C24 C25 1.376(5) . ? C25 C26 1.389(4) . ? C21' C26' 1.385(4) . ? C21' C22' 1.398(4) . ? C22' C23' 1.391(4) . ? C23' C24' 1.377(4) . ? C24' C25' 1.376(4) . ? C25' C26' 1.388(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O11 B1 O12 117.1(3) . . ? O11 B1 C12 119.3(3) . . ? O12 B1 C12 123.5(3) . . ? C16 C11 C12 118.7(3) . . ? C16 C11 C11' 119.5(3) . . ? C12 C11 C11' 121.7(3) . . ? C11 C12 C13 118.8(3) . . ? C11 C12 B1 124.3(3) . . ? C13 C12 B1 116.8(3) . . ? C14 C13 C12 120.9(3) . . ? C15 C14 C13 119.4(3) . . ? C14 C15 C16 120.8(4) . . ? C15 C16 C11 121.5(4) . . ? C16' C11' C12' 117.4(3) . . ? C16' C11' C11 121.1(3) . . ? C12' C11' C11 121.4(3) . . ? C13' C12' C11' 121.0(3) . . ? C14' C13' C12' 120.1(3) . . ? C13' C14' C15' 120.0(3) . . ? C16' C15' C14' 120.2(3) . . ? C15' C16' C11' 121.2(3) . . ? O21 B2 O22 117.3(3) . . ? O21 B2 C22 125.0(3) . . ? O22 B2 C22 117.6(3) . . ? C26 C21 C22 118.9(3) . . ? C26 C21 C21' 119.8(3) . . ? C22 C21 C21' 121.3(3) . . ? C23 C22 C21 118.5(3) . . ? C23 C22 B2 116.6(3) . . ? C21 C22 B2 124.8(3) . . ? C24 C23 C22 121.9(3) . . ? C25 C24 C23 119.0(3) . . ? C24 C25 C26 120.4(3) . . ? C21 C26 C25 121.2(3) . . ? C26' C21' C22' 118.7(3) . . ? C26' C21' C21 120.9(3) . . ? C22' C21' C21 120.4(3) . . ? C23' C22' C21' 120.1(3) . . ? C24' C23' C22' 120.1(3) . . ? C25' C24' C23' 120.3(3) . . ? C24' C25' C26' 119.8(3) . . ? C21' C26' C25' 120.9(3) . . ? 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 C16 C11 C12 C13 -0.6(4) . . . . ? C11' C11 C12 C13 175.7(3) . . . . ? C16 C11 C12 B1 175.0(3) . . . . ? C11' C11 C12 B1 -8.8(4) . . . . ? O11 B1 C12 C11 133.5(3) . . . . ? O12 B1 C12 C11 -50.9(4) . . . . ? O11 B1 C12 C13 -50.9(4) . . . . ? O12 B1 C12 C13 124.6(3) . . . . ? C11 C12 C13 C14 0.2(4) . . . . ? B1 C12 C13 C14 -175.6(3) . . . . ? C12 C13 C14 C15 0.1(5) . . . . ? C13 C14 C15 C16 -0.2(5) . . . . ? C14 C15 C16 C11 -0.1(5) . . . . ? C12 C11 C16 C15 0.5(5) . . . . ? C11' C11 C16 C15 -175.8(3) . . . . ? C16 C11 C11' C16' 130.9(3) . . . . ? C12 C11 C11' C16' -45.3(4) . . . . ? C16 C11 C11' C12' -46.4(4) . . . . ? C12 C11 C11' C12' 137.4(3) . . . . ? C16' C11' C12' C13' -0.4(5) . . . . ? C11 C11' C12' C13' 177.0(3) . . . . ? C11' C12' C13' C14' -0.3(5) . . . . ? C12' C13' C14' C15' 1.1(5) . . . . ? C13' C14' C15' C16' -1.1(5) . . . . ? C14' C15' C16' C11' 0.3(5) . . . . ? C12' C11' C16' C15' 0.4(4) . . . . ? C11 C11' C16' C15' -177.0(3) . . . . ? C26 C21 C22 C23 1.5(4) . . . . ? C21' C21 C22 C23 -176.6(3) . . . . ? C26 C21 C22 B2 -174.5(3) . . . . ? C21' C21 C22 B2 7.4(4) . . . . ? O21 B2 C22 C23 -126.7(3) . . . . ? O22 B2 C22 C23 49.6(3) . . . . ? O21 B2 C22 C21 49.4(4) . . . . ? O22 B2 C22 C21 -134.3(3) . . . . ? C21 C22 C23 C24 -1.3(4) . . . . ? B2 C22 C23 C24 175.0(3) . . . . ? C22 C23 C24 C25 0.7(4) . . . . ? C23 C24 C25 C26 -0.3(4) . . . . ? C22 C21 C26 C25 -1.1(4) . . . . ? C21' C21 C26 C25 177.1(3) . . . . ? C24 C25 C26 C21 0.5(4) . . . . ? C26 C21 C21' C26' 48.0(4) . . . . ? C22 C21 C21' C26' -133.9(3) . . . . ? C26 C21 C21' C22' -129.6(3) . . . . ? C22 C21 C21' C22' 48.5(4) . . . . ? C26' C21' C22' C23' 0.8(4) . . . . ? C21 C21' C22' C23' 178.5(3) . . . . ? C21' C22' C23' C24' -0.2(4) . . . . ? C22' C23' C24' C25' 0.1(5) . . . . ? C23' C24' C25' C26' -0.6(5) . . . . ? C22' C21' C26' C25' -1.3(4) . . . . ? C21 C21' C26' C25' -178.9(3) . . . . ? C24' C25' C26' C21' 1.2(5) . . . . ? _diffrn_measured_fraction_theta_max 0.962 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.962 _refine_diff_density_max 0.353 _refine_diff_density_min -0.282 _refine_diff_density_rms 0.065 # Attachment '9.cif' data_aba2 _database_code_depnum_ccdc_archive 'CCDC 670996' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H17 B O2' _chemical_formula_weight 192.06 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Aba2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/2, -y+1, z+1/2' '-x+1/2, y+1, z+1/2' _cell_length_a 31.624(4) _cell_length_b 15.1613(14) _cell_length_c 9.1559(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4389.9(10) _cell_formula_units_Z 16 _cell_measurement_temperature 108(2) _cell_measurement_reflns_used 7928 _cell_measurement_theta_min 2.5860 _cell_measurement_theta_max 29.9991 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.359 _exptl_crystal_size_mid 0.313 _exptl_crystal_size_min 0.204 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.162 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1664 _exptl_absorpt_coefficient_mu 0.076 _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 108(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 'Sapphire2-CCD, Oxford Diffraction' _diffrn_measurement_method '835 images at 1.0 deg in \w and 30 sec' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18618 _diffrn_reflns_av_R_equivalents 0.0360 _diffrn_reflns_av_sigmaI/netI 0.0317 _diffrn_reflns_limit_h_min -38 _diffrn_reflns_limit_h_max 41 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.68 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2681 _reflns_number_gt 2232 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD 1.171.29, Oxford Diffraction' _computing_cell_refinement 'CrysAlis RED 1.171.29, Oxford Diffraction' _computing_data_reduction 'CrysAlis RED 1.171.29, Oxford Diffraction' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXL-97 _computing_publication_material SHELXL-97 _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^)+(0.0635P)^2^+0.0000P] 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 mixed _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 -10(10) _refine_ls_number_reflns 2681 _refine_ls_number_parameters 279 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0502 _refine_ls_R_factor_gt 0.0406 _refine_ls_wR_factor_ref 0.1014 _refine_ls_wR_factor_gt 0.0989 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.076 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.001 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 0.10800(8) 0.11049(17) 0.9642(3) 0.0232(6) Uani 1 1 d . . . O1 O 0.09356(5) 0.10872(11) 1.10298(19) 0.0277(4) Uani 1 1 d . . . H1 H 0.0762(9) 0.1549(18) 1.115(3) 0.030(7) Uiso 1 1 d . . . O2 O 0.09432(5) 0.17927(12) 0.8780(2) 0.0294(4) Uani 1 1 d . . . H2 H 0.1053(10) 0.177(2) 0.785(4) 0.053(10) Uiso 1 1 d . . . C1 C 0.13844(7) 0.03706(14) 0.9034(3) 0.0219(5) Uani 1 1 d . . . C2 C 0.12188(7) -0.03483(15) 0.8278(3) 0.0227(5) Uani 1 1 d . . . C3 C 0.14885(7) -0.10073(15) 0.7735(3) 0.0256(5) Uani 1 1 d . . . C4 C 0.19245(7) -0.09290(15) 0.7931(3) 0.0266(5) Uani 1 1 d . . . C5 C 0.20956(7) -0.01961(15) 0.8659(3) 0.0264(5) Uani 1 1 d . . . C6 C 0.18248(7) 0.04475(14) 0.9216(3) 0.0234(5) Uani 1 1 d . . . C7 C 0.07449(8) -0.04140(16) 0.8033(3) 0.0289(6) Uani 1 1 d . . . H7A H 0.0604 0.0089 0.8496 0.043 Uiso 1 1 calc R . . H7B H 0.0639 -0.0963 0.8462 0.043 Uiso 1 1 calc R . . H7C H 0.0686 -0.0410 0.6982 0.043 Uiso 1 1 calc R . . C8 C 0.13045(9) -0.17947(17) 0.6947(3) 0.0377(7) Uani 1 1 d . . . H8A H 0.0996 -0.1744 0.6920 0.057 Uiso 1 1 calc R . . H8B H 0.1384 -0.2336 0.7462 0.057 Uiso 1 1 calc R . . H8C H 0.1415 -0.1814 0.5947 0.057 Uiso 1 1 calc R . . C9 C 0.22153(9) -0.16436(17) 0.7344(4) 0.0421(7) Uani 1 1 d . . . H9A H 0.2078 -0.2220 0.7445 0.063 Uiso 1 1 calc R . . H9B H 0.2480 -0.1642 0.7898 0.063 Uiso 1 1 calc R . . H9C H 0.2275 -0.1530 0.6311 0.063 Uiso 1 1 calc R . . C10 C 0.25688(8) -0.00936(17) 0.8843(4) 0.0399(7) Uani 1 1 d . . . H10A H 0.2657 0.0483 0.8466 0.060 Uiso 1 1 calc R . . H10B H 0.2714 -0.0561 0.8301 0.060 Uiso 1 1 calc R . . H10C H 0.2641 -0.0136 0.9881 0.060 Uiso 1 1 calc R . . C11 C 0.20002(8) 0.12388(16) 1.0023(3) 0.0332(6) Uani 1 1 d . . . H11A H 0.1766 0.1593 1.0409 0.050 Uiso 1 1 calc R . . H11B H 0.2169 0.1598 0.9351 0.050 Uiso 1 1 calc R . . H11C H 0.2179 0.1038 1.0832 0.050 Uiso 1 1 calc R . . B2 B -0.00293(8) 0.23721(15) 1.0277(3) 0.0200(5) Uani 1 1 d . . . O3 O 0.01090(5) 0.21846(11) 0.88975(18) 0.0253(4) Uani 1 1 d . . . H3 H 0.0361(11) 0.215(2) 0.878(4) 0.049(10) Uiso 1 1 d . . . O4 O 0.02627(5) 0.23648(11) 1.13689(19) 0.0241(4) Uani 1 1 d . . . H4 H 0.0141(10) 0.252(2) 1.217(4) 0.045(9) Uiso 1 1 d . . . C12 C -0.05153(7) 0.25780(14) 1.0472(2) 0.0183(5) Uani 1 1 d . . . C13 C -0.06789(7) 0.33925(14) 0.9991(2) 0.0184(5) Uani 1 1 d . . . C14 C -0.11128(7) 0.35563(15) 1.0072(3) 0.0204(5) Uani 1 1 d . . . C15 C -0.13835(7) 0.29028(14) 1.0638(3) 0.0219(5) Uani 1 1 d . . . C16 C -0.12194(7) 0.21011(14) 1.1162(3) 0.0204(5) Uani 1 1 d . . . C17 C -0.07843(7) 0.19453(13) 1.1082(2) 0.0185(5) Uani 1 1 d . . . C18 C -0.03805(7) 0.40887(14) 0.9407(3) 0.0237(5) Uani 1 1 d . . . H18A H -0.0455 0.4226 0.8393 0.036 Uiso 1 1 calc R . . H18B H -0.0090 0.3868 0.9448 0.036 Uiso 1 1 calc R . . H18C H -0.0404 0.4624 1.0003 0.036 Uiso 1 1 calc R . . C19 C -0.12938(8) 0.44244(15) 0.9542(3) 0.0279(5) Uani 1 1 d . . . H19A H -0.1063 0.4842 0.9364 0.042 Uiso 1 1 calc R . . H19B H -0.1485 0.4665 1.0285 0.042 Uiso 1 1 calc R . . H19C H -0.1451 0.4327 0.8633 0.042 Uiso 1 1 calc R . . C20 C -0.18566(7) 0.30732(17) 1.0686(3) 0.0339(6) Uani 1 1 d . . . H20A H -0.2007 0.2512 1.0794 0.051 Uiso 1 1 calc R . . H20B H -0.1945 0.3361 0.9777 0.051 Uiso 1 1 calc R . . H20C H -0.1923 0.3457 1.1516 0.051 Uiso 1 1 calc R . . C21 C -0.15099(8) 0.14268(17) 1.1845(3) 0.0298(6) Uani 1 1 d . . . H21A H -0.1679 0.1708 1.2611 0.045 Uiso 1 1 calc R . . H21B H -0.1341 0.0950 1.2272 0.045 Uiso 1 1 calc R . . H21C H -0.1698 0.1184 1.1095 0.045 Uiso 1 1 calc R . . C22 C -0.06032(7) 0.10926(14) 1.1688(3) 0.0246(5) Uani 1 1 d . . . H22A H -0.0303 0.1049 1.1427 0.037 Uiso 1 1 calc R . . H22B H -0.0757 0.0590 1.1273 0.037 Uiso 1 1 calc R . . H22C H -0.0633 0.1088 1.2753 0.037 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 B1 0.0197(13) 0.0248(13) 0.0250(14) 0.0021(11) -0.0018(11) -0.0031(10) O1 0.0334(9) 0.0266(8) 0.0232(9) 0.0016(8) 0.0037(8) 0.0072(7) O2 0.0264(9) 0.0350(9) 0.0268(10) 0.0093(8) 0.0096(8) 0.0122(7) C1 0.0226(11) 0.0210(11) 0.0220(12) 0.0025(10) 0.0006(10) 0.0003(9) C2 0.0206(11) 0.0235(11) 0.0241(13) 0.0023(9) 0.0000(9) -0.0006(9) C3 0.0275(13) 0.0222(11) 0.0272(14) -0.0015(10) 0.0022(11) -0.0010(9) C4 0.0262(12) 0.0232(11) 0.0304(13) 0.0016(10) 0.0045(11) 0.0027(9) C5 0.0202(11) 0.0256(11) 0.0334(15) 0.0019(11) -0.0001(11) 0.0015(9) C6 0.0210(12) 0.0208(10) 0.0284(14) -0.0016(10) 0.0000(10) -0.0006(9) C7 0.0259(13) 0.0328(12) 0.0281(14) 0.0000(11) -0.0031(11) -0.0037(10) C8 0.0378(15) 0.0328(14) 0.0426(17) -0.0091(13) 0.0015(13) -0.0052(12) C9 0.0370(15) 0.0319(14) 0.0573(19) -0.0082(14) 0.0092(14) 0.0071(12) C10 0.0235(14) 0.0371(13) 0.0592(19) -0.0074(14) 0.0034(14) 0.0016(11) C11 0.0254(13) 0.0280(12) 0.0463(16) -0.0090(12) -0.0035(12) -0.0011(10) B2 0.0180(13) 0.0187(11) 0.0233(14) 0.0022(10) 0.0009(10) 0.0000(10) O3 0.0192(9) 0.0389(10) 0.0178(8) 0.0004(7) 0.0013(8) 0.0072(7) O4 0.0170(8) 0.0364(9) 0.0188(9) -0.0029(8) -0.0002(7) 0.0040(7) C12 0.0176(11) 0.0228(10) 0.0146(11) -0.0023(9) 0.0001(9) 0.0005(8) C13 0.0205(11) 0.0219(10) 0.0130(10) -0.0017(9) -0.0005(10) -0.0010(9) C14 0.0199(11) 0.0248(10) 0.0166(11) -0.0017(9) -0.0025(9) 0.0025(9) C15 0.0182(11) 0.0274(11) 0.0201(12) -0.0016(9) -0.0016(10) -0.0011(9) C16 0.0190(11) 0.0236(10) 0.0188(11) -0.0002(10) -0.0012(10) -0.0036(8) C17 0.0221(11) 0.0190(10) 0.0143(11) -0.0019(9) -0.0025(9) 0.0005(8) C18 0.0252(12) 0.0208(11) 0.0250(12) 0.0005(10) 0.0031(10) 0.0003(9) C19 0.0238(13) 0.0272(12) 0.0327(14) 0.0036(11) 0.0013(11) 0.0044(10) C20 0.0188(12) 0.0399(14) 0.0431(16) 0.0047(12) -0.0016(12) 0.0028(10) C21 0.0232(13) 0.0320(13) 0.0343(15) 0.0037(11) 0.0001(11) -0.0068(10) C22 0.0257(12) 0.0200(11) 0.0281(13) 0.0035(10) -0.0015(10) -0.0004(9) _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 1.350(3) . ? B1 O2 1.377(3) . ? B1 C1 1.574(4) . ? C1 C2 1.393(3) . ? C1 C6 1.407(3) . ? C2 C3 1.405(3) . ? C2 C7 1.518(3) . ? C3 C4 1.395(3) . ? C3 C8 1.511(3) . ? C4 C5 1.404(3) . ? C4 C9 1.519(3) . ? C5 C6 1.395(3) . ? C5 C10 1.514(3) . ? C6 C11 1.514(3) . ? B2 O4 1.361(3) . ? B2 O3 1.367(3) . ? B2 C12 1.578(3) . ? C12 C17 1.398(3) . ? C12 C13 1.409(3) . ? C13 C14 1.397(3) . ? C13 C18 1.513(3) . ? C14 C15 1.408(3) . ? C14 C19 1.515(3) . ? C15 C16 1.406(3) . ? C15 C20 1.519(3) . ? C16 C17 1.398(3) . ? C16 C21 1.510(3) . ? C17 C22 1.519(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 116.6(2) . . ? O1 B1 C1 121.7(2) . . ? O2 B1 C1 121.7(2) . . ? C2 C1 C6 119.7(2) . . ? C2 C1 B1 120.0(2) . . ? C6 C1 B1 120.3(2) . . ? C1 C2 C3 120.3(2) . . ? C1 C2 C7 119.7(2) . . ? C3 C2 C7 120.0(2) . . ? C4 C3 C2 119.6(2) . . ? C4 C3 C8 120.6(2) . . ? C2 C3 C8 119.8(2) . . ? C3 C4 C5 120.6(2) . . ? C3 C4 C9 119.5(2) . . ? C5 C4 C9 119.9(2) . . ? C6 C5 C4 119.4(2) . . ? C6 C5 C10 119.6(2) . . ? C4 C5 C10 121.0(2) . . ? C5 C6 C1 120.4(2) . . ? C5 C6 C11 120.5(2) . . ? C1 C6 C11 119.1(2) . . ? O4 B2 O3 117.4(2) . . ? O4 B2 C12 125.4(2) . . ? O3 B2 C12 117.2(2) . . ? C17 C12 C13 120.17(19) . . ? C17 C12 B2 120.12(18) . . ? C13 C12 B2 119.69(19) . . ? C14 C13 C12 120.0(2) . . ? C14 C13 C18 120.48(19) . . ? C12 C13 C18 119.52(19) . . ? C13 C14 C15 119.5(2) . . ? C13 C14 C19 120.6(2) . . ? C15 C14 C19 120.0(2) . . ? C16 C15 C14 120.6(2) . . ? C16 C15 C20 120.1(2) . . ? C14 C15 C20 119.3(2) . . ? C17 C16 C15 119.44(19) . . ? C17 C16 C21 120.40(19) . . ? C15 C16 C21 120.1(2) . . ? C16 C17 C12 120.25(18) . . ? C16 C17 C22 119.73(19) . . ? C12 C17 C22 120.01(19) . . ? 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 O1 B1 C1 C2 94.8(3) . . . . ? O2 B1 C1 C2 -84.4(3) . . . . ? O1 B1 C1 C6 -86.8(3) . . . . ? O2 B1 C1 C6 94.0(3) . . . . ? C6 C1 C2 C3 1.8(4) . . . . ? B1 C1 C2 C3 -179.9(2) . . . . ? C6 C1 C2 C7 -177.8(2) . . . . ? B1 C1 C2 C7 0.6(3) . . . . ? C1 C2 C3 C4 -1.3(4) . . . . ? C7 C2 C3 C4 178.3(2) . . . . ? C1 C2 C3 C8 178.6(2) . . . . ? C7 C2 C3 C8 -1.9(3) . . . . ? C2 C3 C4 C5 -0.3(4) . . . . ? C8 C3 C4 C5 179.8(2) . . . . ? C2 C3 C4 C9 179.9(2) . . . . ? C8 C3 C4 C9 0.0(4) . . . . ? C3 C4 C5 C6 1.4(4) . . . . ? C9 C4 C5 C6 -178.8(3) . . . . ? C3 C4 C5 C10 -178.4(3) . . . . ? C9 C4 C5 C10 1.3(4) . . . . ? C4 C5 C6 C1 -0.9(4) . . . . ? C10 C5 C6 C1 178.9(3) . . . . ? C4 C5 C6 C11 179.2(2) . . . . ? C10 C5 C6 C11 -1.0(4) . . . . ? C2 C1 C6 C5 -0.7(4) . . . . ? B1 C1 C6 C5 -179.0(2) . . . . ? C2 C1 C6 C11 179.2(2) . . . . ? B1 C1 C6 C11 0.9(4) . . . . ? O4 B2 C12 C17 -75.5(3) . . . . ? O3 B2 C12 C17 104.4(3) . . . . ? O4 B2 C12 C13 106.3(3) . . . . ? O3 B2 C12 C13 -73.8(3) . . . . ? C17 C12 C13 C14 -2.4(3) . . . . ? B2 C12 C13 C14 175.8(2) . . . . ? C17 C12 C13 C18 176.8(2) . . . . ? B2 C12 C13 C18 -5.0(3) . . . . ? C12 C13 C14 C15 0.1(3) . . . . ? C18 C13 C14 C15 -179.1(2) . . . . ? C12 C13 C14 C19 -179.2(2) . . . . ? C18 C13 C14 C19 1.6(3) . . . . ? C13 C14 C15 C16 2.0(3) . . . . ? C19 C14 C15 C16 -178.7(2) . . . . ? C13 C14 C15 C20 -178.3(2) . . . . ? C19 C14 C15 C20 1.0(3) . . . . ? C14 C15 C16 C17 -1.7(3) . . . . ? C20 C15 C16 C17 178.6(2) . . . . ? C14 C15 C16 C21 176.5(2) . . . . ? C20 C15 C16 C21 -3.2(3) . . . . ? C15 C16 C17 C12 -0.6(3) . . . . ? C21 C16 C17 C12 -178.9(2) . . . . ? C15 C16 C17 C22 178.1(2) . . . . ? C21 C16 C17 C22 -0.1(3) . . . . ? C13 C12 C17 C16 2.7(3) . . . . ? B2 C12 C17 C16 -175.5(2) . . . . ? C13 C12 C17 C22 -176.1(2) . . . . ? B2 C12 C17 C22 5.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.290 _refine_diff_density_min -0.145 _refine_diff_density_rms 0.046