Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'John Lavigne' _publ_contact_author_address ; Department of Chemistry & Biochemistry University of South Carolina GSRC 430 631 Sumter Street Columbia SC 29208 UNITED STATES OF AMERICA ; _publ_contact_author_email LAVIGNE@MAIL.CHEM.SC.EDU _publ_section_title ; Substituent Effects on the Structure and Supramolecular Assembly of Bis(dioxaborole)s ; loop_ _publ_author_name 'John Lavigne' 'Weijun Niu.' 'Brett M. Rambo' 'Mark D. Smith' data_wn1173m _database_code_depnum_ccdc_archive 'CCDC 261873' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H12 B2 O4' _chemical_formula_sum 'C18 H12 B2 O4' _chemical_formula_weight 313.90 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 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' 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 11.2841(9) _cell_length_b 5.5991(4) _cell_length_c 22.8642(18) _cell_angle_alpha 90.00 _cell_angle_beta 95.6950(10) _cell_angle_gamma 90.00 _cell_volume 1437.45(19) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3575 _cell_measurement_theta_min 3.582 _cell_measurement_theta_max 26.360 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.450 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.100 _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 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX CCD diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 5636 _diffrn_reflns_av_R_equivalents 0.0532 _diffrn_reflns_av_sigmaI/netI 0.0425 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 26.37 _reflns_number_total 1464 _reflns_number_gt 1259 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART NT V5.625 (Bruker, 1998)' _computing_cell_refinement 'SAINT+ NT V6.22 (Bruker, 2001)' _computing_data_reduction 'SAINT+ NT V6.22' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL V6.1 (Sheldrick, 2000)' _computing_publication_material 'SHELXTL V6.1' _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^)+(0.0447P)^2^+0.8701P] 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 refU _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1464 _refine_ls_number_parameters 115 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0475 _refine_ls_R_factor_gt 0.0414 _refine_ls_wR_factor_ref 0.0963 _refine_ls_wR_factor_gt 0.0933 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group B1 B 0.26687(14) 0.3403(3) 0.58152(7) 0.0278(4) Uani 1 1 d . . . O1 O 0.16913(8) 0.22744(18) 0.60173(4) 0.0286(3) Uani 1 1 d . . . O2 O 0.37285(8) 0.23118(18) 0.60318(4) 0.0292(3) Uani 1 1 d . . . C1 C 0.25815(12) 0.5554(3) 0.53926(6) 0.0271(3) Uani 1 1 d . . . C2 C 0.14778(12) 0.6528(3) 0.51905(6) 0.0300(3) Uani 1 1 d . . . H2 H 0.0773 0.5873 0.5321 0.030(4) Uiso 1 1 calc R . . C3 C 0.13950(12) 0.8433(3) 0.48032(6) 0.0300(3) Uani 1 1 d . . . H3 H 0.0634 0.9061 0.4669 0.031(4) Uiso 1 1 calc R . . C4 C 0.21627(12) 0.0418(3) 0.63665(6) 0.0265(3) Uani 1 1 d . . . C5 C 0.33926(12) 0.0444(3) 0.63759(6) 0.0265(3) Uani 1 1 d . . . C6 C 0.40997(13) -0.1233(3) 0.66780(6) 0.0314(4) Uani 1 1 d . . . H6 H 0.4942 -0.1217 0.6681 0.038(4) Uiso 1 1 calc R . . C7 C 0.35127(13) -0.2957(3) 0.69801(6) 0.0319(4) Uani 1 1 d . . . H7 H 0.3967 -0.4147 0.7197 0.037(4) Uiso 1 1 calc R . . C8 C 0.22783(13) -0.2980(3) 0.69720(6) 0.0315(4) Uani 1 1 d . . . H8 H 0.1909 -0.4181 0.7185 0.036(4) Uiso 1 1 calc R . . C9 C 0.15748(12) -0.1282(3) 0.66593(6) 0.0303(3) Uani 1 1 d . . . H9 H 0.0731 -0.1298 0.6649 0.033(4) 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 0.0282(8) 0.0297(9) 0.0255(8) -0.0076(7) 0.0026(6) -0.0012(7) O1 0.0261(5) 0.0284(6) 0.0311(5) 0.0005(4) 0.0015(4) 0.0003(4) O2 0.0260(5) 0.0294(6) 0.0325(5) 0.0010(4) 0.0043(4) -0.0011(4) C1 0.0296(7) 0.0270(8) 0.0244(7) -0.0057(6) 0.0023(5) -0.0008(6) C2 0.0253(7) 0.0342(9) 0.0306(7) -0.0023(6) 0.0038(5) -0.0040(6) C3 0.0250(7) 0.0342(9) 0.0305(7) -0.0014(6) 0.0015(5) 0.0027(6) C4 0.0276(7) 0.0268(8) 0.0248(7) -0.0045(6) 0.0006(5) 0.0012(6) C5 0.0268(7) 0.0266(8) 0.0264(7) -0.0035(6) 0.0040(5) -0.0021(6) C6 0.0266(7) 0.0341(9) 0.0333(8) -0.0027(6) 0.0019(6) 0.0024(6) C7 0.0358(8) 0.0296(9) 0.0299(7) -0.0001(6) 0.0004(6) 0.0043(7) C8 0.0365(8) 0.0295(8) 0.0288(7) -0.0010(6) 0.0045(6) -0.0050(6) C9 0.0263(7) 0.0335(9) 0.0313(7) -0.0037(6) 0.0037(6) -0.0033(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 B1 O1 1.3894(19) . ? B1 O2 1.3897(19) . ? B1 C1 1.541(2) . ? O1 C4 1.3843(17) . ? O2 C5 1.3842(17) . ? C1 C2 1.395(2) . ? C1 C3 1.399(2) 7_566 ? C2 C3 1.384(2) . ? C2 H2 0.9500 . ? C3 C1 1.399(2) 7_566 ? C3 H3 0.9500 . ? C4 C9 1.372(2) . ? C4 C5 1.3859(19) . ? C5 C6 1.373(2) . ? C6 C7 1.392(2) . ? C6 H6 0.9500 . ? C7 C8 1.391(2) . ? C7 H7 0.9500 . ? C8 C9 1.390(2) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? 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 111.40(14) . . ? O1 B1 C1 124.10(13) . . ? O2 B1 C1 124.48(13) . . ? C4 O1 B1 105.13(11) . . ? C5 O2 B1 105.09(11) . . ? C2 C1 C3 118.27(14) . 7_566 ? C2 C1 B1 120.80(13) . . ? C3 C1 B1 120.93(13) 7_566 . ? C3 C2 C1 120.95(13) . . ? C3 C2 H2 119.5 . . ? C1 C2 H2 119.5 . . ? C2 C3 C1 120.78(14) . 7_566 ? C2 C3 H3 119.6 . . ? C1 C3 H3 119.6 7_566 . ? C9 C4 O1 128.72(13) . . ? C9 C4 C5 122.11(14) . . ? O1 C4 C5 109.15(12) . . ? C6 C5 O2 128.63(13) . . ? C6 C5 C4 122.13(14) . . ? O2 C5 C4 109.22(12) . . ? C5 C6 C7 116.24(13) . . ? C5 C6 H6 121.9 . . ? C7 C6 H6 121.9 . . ? C8 C7 C6 121.67(14) . . ? C8 C7 H7 119.2 . . ? C6 C7 H7 119.2 . . ? C9 C8 C7 121.35(14) . . ? C9 C8 H8 119.3 . . ? C7 C8 H8 119.3 . . ? C4 C9 C8 116.51(13) . . ? C4 C9 H9 121.7 . . ? C8 C9 H9 121.7 . . ? 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 O2 B1 O1 C4 -0.40(15) . . . . ? C1 B1 O1 C4 178.23(13) . . . . ? O1 B1 O2 C5 0.30(15) . . . . ? C1 B1 O2 C5 -178.32(13) . . . . ? O1 B1 C1 C2 0.8(2) . . . . ? O2 B1 C1 C2 179.27(13) . . . . ? O1 B1 C1 C3 -178.53(13) . . . 7_566 ? O2 B1 C1 C3 -0.1(2) . . . 7_566 ? C3 C1 C2 C3 0.5(2) 7_566 . . . ? B1 C1 C2 C3 -178.88(13) . . . . ? C1 C2 C3 C1 -0.5(2) . . . 7_566 ? B1 O1 C4 C9 -178.17(14) . . . . ? B1 O1 C4 C5 0.34(14) . . . . ? B1 O2 C5 C6 178.13(14) . . . . ? B1 O2 C5 C4 -0.08(15) . . . . ? C9 C4 C5 C6 0.1(2) . . . . ? O1 C4 C5 C6 -178.52(12) . . . . ? C9 C4 C5 O2 178.47(12) . . . . ? O1 C4 C5 O2 -0.17(15) . . . . ? O2 C5 C6 C7 -178.55(13) . . . . ? C4 C5 C6 C7 -0.5(2) . . . . ? C5 C6 C7 C8 0.4(2) . . . . ? C6 C7 C8 C9 0.2(2) . . . . ? O1 C4 C9 C8 178.82(13) . . . . ? C5 C4 C9 C8 0.5(2) . . . . ? C7 C8 C9 C4 -0.6(2) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.195 _refine_diff_density_min -0.291 _refine_diff_density_rms 0.076 data_wn2779t _database_code_depnum_ccdc_archive 'CCDC 261874' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H36 B2 O4' _chemical_formula_sum 'C30 H36 B2 O4' _chemical_formula_weight 482.21 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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 4.8191(5) _cell_length_b 9.7761(10) _cell_length_c 14.2815(14) _cell_angle_alpha 77.386(2) _cell_angle_beta 82.507(2) _cell_angle_gamma 84.416(2) _cell_volume 649.33(11) _cell_formula_units_Z 1 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 2175 _cell_measurement_theta_min 2.330 _cell_measurement_theta_max 25.016 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.233 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 258 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; Needle segment cut from ca. 2 cm crystal ; _diffrn_ambient_temperature 150(1) _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 'Bruker SMART APEX CCD diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 4742 _diffrn_reflns_av_R_equivalents 0.0421 _diffrn_reflns_av_sigmaI/netI 0.0606 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.47 _diffrn_reflns_theta_max 25.07 _reflns_number_total 2304 _reflns_number_gt 1661 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART NT V5.625 (Bruker, 1998)' _computing_cell_refinement 'SAINT+ NT V6.22 (Bruker, 2001)' _computing_data_reduction 'SAINT+ NT V6.22' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL V6.1 (Sheldrick, 2000)' _computing_publication_material 'SHELXTL V6.1' _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^)+(0.0373P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2304 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0669 _refine_ls_R_factor_gt 0.0451 _refine_ls_wR_factor_ref 0.0954 _refine_ls_wR_factor_gt 0.0890 _refine_ls_goodness_of_fit_ref 0.957 _refine_ls_restrained_S_all 0.957 _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 B1 B 0.4266(4) 0.1962(2) -0.10018(13) 0.0275(5) Uani 1 1 d . . . C1 C 0.2086(3) 0.08960(18) -0.05143(11) 0.0251(4) Uani 1 1 d . . . C2 C 0.0137(4) 0.12710(18) 0.02189(11) 0.0264(4) Uani 1 1 d . . . H2 H 0.0235 0.2162 0.0372 0.032 Uiso 1 1 calc R . . C3 C -0.1933(3) 0.04229(18) 0.07378(11) 0.0257(4) Uani 1 1 d . . . C4 C 0.6711(4) 0.38330(18) -0.12424(12) 0.0285(4) Uani 1 1 d . . . C5 C 0.7674(4) 0.30984(18) -0.19500(12) 0.0277(4) Uani 1 1 d . . . C6 C 0.9843(4) 0.35256(19) -0.26460(12) 0.0341(5) Uani 1 1 d . . . H6 H 1.0504 0.3014 -0.3135 0.041 Uiso 1 1 calc R . . C7 C 1.1012(4) 0.4744(2) -0.25959(13) 0.0372(5) Uani 1 1 d . . . H7 H 1.2510 0.5083 -0.3064 0.045 Uiso 1 1 calc R . . C8 C 1.0045(4) 0.54765(19) -0.18799(13) 0.0379(5) Uani 1 1 d . . . H8 H 1.0904 0.6305 -0.1866 0.045 Uiso 1 1 calc R . . C9 C 0.7854(4) 0.50356(19) -0.11792(13) 0.0350(5) Uani 1 1 d . . . H9 H 0.7187 0.5537 -0.0685 0.042 Uiso 1 1 calc R . . C10 C -0.3877(4) 0.09671(18) 0.15155(11) 0.0280(4) Uani 1 1 d . . . H10A H -0.5641 0.0486 0.1625 0.034 Uiso 1 1 calc R . . H10B H -0.4350 0.1983 0.1283 0.034 Uiso 1 1 calc R . . C11 C -0.2658(4) 0.07571(19) 0.24761(12) 0.0306(5) Uani 1 1 d . . . H11A H -0.2396 -0.0262 0.2752 0.037 Uiso 1 1 calc R . . H11B H -0.0795 0.1147 0.2361 0.037 Uiso 1 1 calc R . . C12 C -0.4551(4) 0.1466(2) 0.31988(12) 0.0341(5) Uani 1 1 d . . . H12A H -0.5229 0.2410 0.2860 0.041 Uiso 1 1 calc R . . H12B H -0.6209 0.0913 0.3438 0.041 Uiso 1 1 calc R . . C13 C -0.3164(4) 0.1623(2) 0.40558(12) 0.0372(5) Uani 1 1 d . . . H13A H -0.1438 0.2125 0.3819 0.045 Uiso 1 1 calc R . . H13B H -0.2603 0.0678 0.4423 0.045 Uiso 1 1 calc R . . C14 C -0.5042(4) 0.2418(2) 0.47322(13) 0.0456(6) Uani 1 1 d . . . H14A H -0.5795 0.3317 0.4351 0.055 Uiso 1 1 calc R . . H14B H -0.6651 0.1857 0.5034 0.055 Uiso 1 1 calc R . . C15 C -0.3525(5) 0.2724(3) 0.55178(15) 0.0645(7) Uani 1 1 d . . . H15A H -0.2813 0.1838 0.5909 0.097 Uiso 1 1 calc R . . H15B H -0.4825 0.3236 0.5930 0.097 Uiso 1 1 calc R . . H15C H -0.1952 0.3297 0.5224 0.097 Uiso 1 1 calc R . . O1 O 0.4560(2) 0.31473(12) -0.06392(7) 0.0293(3) Uani 1 1 d . . . O2 O 0.6168(2) 0.19192(12) -0.18174(8) 0.0299(3) 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 B1 0.0253(12) 0.0326(12) 0.0260(10) -0.0082(9) -0.0074(9) 0.0022(10) C1 0.0224(10) 0.0299(10) 0.0241(9) -0.0066(8) -0.0076(8) 0.0011(8) C2 0.0254(10) 0.0277(10) 0.0285(9) -0.0093(8) -0.0071(8) -0.0007(8) C3 0.0210(10) 0.0311(11) 0.0267(9) -0.0077(8) -0.0082(8) 0.0005(8) C4 0.0237(11) 0.0294(11) 0.0313(10) -0.0055(8) -0.0006(8) -0.0025(8) C5 0.0247(11) 0.0287(10) 0.0304(9) -0.0061(8) -0.0046(8) -0.0035(8) C6 0.0312(12) 0.0386(12) 0.0320(10) -0.0096(9) 0.0002(9) -0.0002(9) C7 0.0312(12) 0.0384(12) 0.0389(11) -0.0017(9) 0.0013(9) -0.0087(9) C8 0.0355(12) 0.0304(11) 0.0476(11) -0.0076(9) -0.0010(10) -0.0084(9) C9 0.0361(12) 0.0298(11) 0.0399(10) -0.0107(9) -0.0030(9) -0.0001(9) C10 0.0242(11) 0.0288(11) 0.0328(9) -0.0112(8) -0.0021(8) -0.0016(8) C11 0.0309(11) 0.0318(11) 0.0302(9) -0.0102(8) -0.0011(8) -0.0021(9) C12 0.0293(11) 0.0418(12) 0.0330(10) -0.0133(9) -0.0001(9) -0.0027(9) C13 0.0358(12) 0.0443(12) 0.0331(10) -0.0135(9) 0.0007(9) -0.0043(10) C14 0.0386(13) 0.0642(15) 0.0392(11) -0.0247(10) 0.0054(10) -0.0111(11) C15 0.0569(16) 0.096(2) 0.0510(13) -0.0406(13) 0.0064(12) -0.0162(14) O1 0.0277(7) 0.0306(7) 0.0307(6) -0.0098(5) 0.0010(6) -0.0050(6) O2 0.0291(7) 0.0325(7) 0.0303(6) -0.0119(5) 0.0003(6) -0.0060(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 B1 O2 1.390(2) . ? B1 O1 1.395(2) . ? B1 C1 1.543(3) . ? C1 C2 1.399(2) . ? C1 C3 1.405(2) 2 ? C2 C3 1.390(2) . ? C2 H2 0.9500 . ? C3 C1 1.405(2) 2 ? C3 C10 1.511(2) . ? C4 C9 1.371(2) . ? C4 C5 1.372(2) . ? C4 O1 1.3843(19) . ? C5 C6 1.374(2) . ? C5 O2 1.3871(18) . ? C6 C7 1.385(2) . ? C6 H6 0.9500 . ? C7 C8 1.381(2) . ? C7 H7 0.9500 . ? C8 C9 1.388(2) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 C11 1.527(2) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.524(2) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.511(2) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.523(2) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.512(3) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 B1 O1 110.46(15) . . ? O2 B1 C1 127.91(15) . . ? O1 B1 C1 121.64(15) . . ? C2 C1 C3 117.72(15) . 2 ? C2 C1 B1 117.02(15) . . ? C3 C1 B1 125.26(15) 2 . ? C3 C2 C1 124.16(15) . . ? C3 C2 H2 117.9 . . ? C1 C2 H2 117.9 . . ? C2 C3 C1 118.12(15) . 2 ? C2 C3 C10 118.14(15) . . ? C1 C3 C10 123.74(15) 2 . ? C9 C4 C5 122.35(16) . . ? C9 C4 O1 128.38(15) . . ? C5 C4 O1 109.26(14) . . ? C4 C5 C6 122.09(16) . . ? C4 C5 O2 109.34(14) . . ? C6 C5 O2 128.56(15) . . ? C5 C6 C7 116.30(16) . . ? C5 C6 H6 121.8 . . ? C7 C6 H6 121.8 . . ? C8 C7 C6 121.42(17) . . ? C8 C7 H7 119.3 . . ? C6 C7 H7 119.3 . . ? C7 C8 C9 121.84(17) . . ? C7 C8 H8 119.1 . . ? C9 C8 H8 119.1 . . ? C4 C9 C8 115.99(16) . . ? C4 C9 H9 122.0 . . ? C8 C9 H9 122.0 . . ? C3 C10 C11 114.04(14) . . ? C3 C10 H10A 108.7 . . ? C11 C10 H10A 108.7 . . ? C3 C10 H10B 108.7 . . ? C11 C10 H10B 108.7 . . ? H10A C10 H10B 107.6 . . ? C12 C11 C10 112.03(15) . . ? C12 C11 H11A 109.2 . . ? C10 C11 H11A 109.2 . . ? C12 C11 H11B 109.2 . . ? C10 C11 H11B 109.2 . . ? H11A C11 H11B 107.9 . . ? C13 C12 C11 114.53(15) . . ? C13 C12 H12A 108.6 . . ? C11 C12 H12A 108.6 . . ? C13 C12 H12B 108.6 . . ? C11 C12 H12B 108.6 . . ? H12A C12 H12B 107.6 . . ? C12 C13 C14 113.39(16) . . ? C12 C13 H13A 108.9 . . ? C14 C13 H13A 108.9 . . ? C12 C13 H13B 108.9 . . ? C14 C13 H13B 108.9 . . ? H13A C13 H13B 107.7 . . ? C15 C14 C13 112.91(17) . . ? C15 C14 H14A 109.0 . . ? C13 C14 H14A 109.0 . . ? C15 C14 H14B 109.0 . . ? C13 C14 H14B 109.0 . . ? H14A C14 H14B 107.8 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C4 O1 B1 105.50(13) . . ? C5 O2 B1 105.44(12) . . ? 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 O2 B1 C1 C2 -171.15(17) . . . . ? O1 B1 C1 C2 9.2(3) . . . . ? O2 B1 C1 C3 9.9(3) . . . 2 ? O1 B1 C1 C3 -169.73(17) . . . 2 ? C3 C1 C2 C3 0.0(3) 2 . . . ? B1 C1 C2 C3 -179.05(16) . . . . ? C1 C2 C3 C1 0.0(3) . . . 2 ? C1 C2 C3 C10 179.55(15) . . . . ? C9 C4 C5 C6 -0.4(3) . . . . ? O1 C4 C5 C6 -179.08(16) . . . . ? C9 C4 C5 O2 178.60(17) . . . . ? O1 C4 C5 O2 -0.1(2) . . . . ? C4 C5 C6 C7 0.0(3) . . . . ? O2 C5 C6 C7 -178.76(18) . . . . ? C5 C6 C7 C8 0.3(3) . . . . ? C6 C7 C8 C9 -0.3(3) . . . . ? C5 C4 C9 C8 0.4(3) . . . . ? O1 C4 C9 C8 178.86(17) . . . . ? C7 C8 C9 C4 -0.1(3) . . . . ? C2 C3 C10 C11 -82.0(2) . . . . ? C1 C3 C10 C11 97.5(2) 2 . . . ? C3 C10 C11 C12 173.58(14) . . . . ? C10 C11 C12 C13 -165.02(15) . . . . ? C11 C12 C13 C14 176.28(15) . . . . ? C12 C13 C14 C15 -172.99(16) . . . . ? C9 C4 O1 B1 -178.16(19) . . . . ? C5 C4 O1 B1 0.47(19) . . . . ? O2 B1 O1 C4 -0.65(19) . . . . ? C1 B1 O1 C4 179.03(16) . . . . ? C4 C5 O2 B1 -0.27(19) . . . . ? C6 C5 O2 B1 178.60(19) . . . . ? O1 B1 O2 C5 0.57(19) . . . . ? C1 B1 O2 C5 -179.08(18) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.07 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.170 _refine_diff_density_min -0.181 _refine_diff_density_rms 0.037