# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1 #TrackingRef 'web_deposit_cif_file_0_PeterNHorton_1364203048.borates.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C4 H20 B6 N2 O14' _chemical_formula_weight 385.08 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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 5.7619(2) _cell_length_b 6.3796(2) _cell_length_c 11.6206(5) _cell_angle_alpha 92.684(2) _cell_angle_beta 98.060(2) _cell_angle_gamma 114.750(2) _cell_volume 381.43(2) _cell_formula_units_Z 1 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 1692 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 _exptl_crystal_description 'cut block' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.676 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 200 _exptl_absorpt_coefficient_mu 0.155 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9877 _exptl_absorpt_correction_T_max 0.9954 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; SADABS was used to perform the Absorption correction Parameter refinement on 6828 reflections reduced R(int) from 0.1092 to 0.0466 Ratio of minimum to maximum apparent transmission: 0.867421 The given Tmin and Tmax were generated using the SHELX SIZE command ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius APEX II CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7312 _diffrn_reflns_av_R_equivalents 0.0440 _diffrn_reflns_av_sigmaI/netI 0.0370 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.54 _diffrn_reflns_theta_max 27.48 _reflns_number_total 1746 _reflns_number_gt 1479 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997a)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997b)' _computing_molecular_graphics 'ORTEP3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 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^)+(0.0194P)^2^+0.3708P] 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 1746 _refine_ls_number_parameters 122 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0525 _refine_ls_R_factor_gt 0.0416 _refine_ls_wR_factor_ref 0.0941 _refine_ls_wR_factor_gt 0.0870 _refine_ls_goodness_of_fit_ref 1.094 _refine_ls_restrained_S_all 1.094 _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 0.0571(4) 0.2765(3) 0.76502(16) 0.0120(4) Uani 1 1 d . . . B2 B 0.1819(4) 0.2948(3) 0.98319(16) 0.0129(4) Uani 1 1 d . . . B3 B 0.2964(4) 0.0608(3) 0.85458(16) 0.0121(4) Uani 1 1 d . . . O1 O 0.0645(2) 0.3537(2) 0.88964(10) 0.0131(3) Uani 1 1 d . . . O2 O 0.3020(2) 0.1472(2) 0.96808(10) 0.0136(3) Uani 1 1 d . . . O3 O 0.1842(2) 0.1169(2) 0.75992(10) 0.0128(3) Uani 1 1 d . . . O4 O -0.2098(2) 0.1609(2) 0.70366(10) 0.0142(3) Uani 1 1 d . . . H4 H -0.3026 0.0718 0.7466 0.021 Uiso 1 1 calc R . . O5 O 0.1923(2) 0.4763(2) 0.70502(10) 0.0146(3) Uani 1 1 d . . . H5 H 0.2449 0.5988 0.7510 0.022 Uiso 1 1 calc R . . O6 O 0.1931(2) 0.3712(2) 1.09591(10) 0.0166(3) Uani 1 1 d . . . H6 H 0.1124 0.4543 1.0971 0.025 Uiso 1 1 calc R . . O7 O 0.4148(2) -0.0845(2) 0.84040(10) 0.0134(3) Uani 1 1 d . . . H7 H 0.4940 -0.0912 0.9056 0.020 Uiso 1 1 calc R . . C11 C 0.5956(3) 0.7477(3) 0.49850(15) 0.0155(4) Uani 1 1 d . . . H11A H 0.4823 0.7846 0.5443 0.019 Uiso 1 1 calc R . . H11B H 0.7175 0.8941 0.4738 0.019 Uiso 1 1 calc R . . C12 C 0.2527(3) 0.3559(3) 0.42581(15) 0.0150(3) Uani 1 1 d . . . H12A H 0.1532 0.2474 0.3542 0.018 Uiso 1 1 calc R . . H12B H 0.1281 0.3801 0.4691 0.018 Uiso 1 1 calc R . . N11 N 0.4340(3) 0.5816(2) 0.39314(12) 0.0134(3) Uani 1 1 d . . . H11C H 0.3402 0.6456 0.3492 0.016 Uiso 1 1 calc R . . H11D H 0.5407 0.5564 0.3479 0.016 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 0.0144(9) 0.0126(9) 0.0105(8) 0.0009(7) 0.0019(7) 0.0073(7) B2 0.0124(9) 0.0140(9) 0.0135(9) 0.0030(7) 0.0027(7) 0.0064(7) B3 0.0109(9) 0.0118(9) 0.0131(8) 0.0013(7) 0.0029(7) 0.0043(7) O1 0.0161(6) 0.0159(6) 0.0109(6) 0.0014(4) 0.0022(4) 0.0102(5) O2 0.0168(6) 0.0158(6) 0.0113(6) 0.0017(4) 0.0016(5) 0.0104(5) O3 0.0157(6) 0.0153(6) 0.0105(5) 0.0011(4) 0.0022(4) 0.0098(5) O4 0.0135(6) 0.0165(6) 0.0133(6) 0.0031(5) 0.0024(5) 0.0071(5) O5 0.0189(6) 0.0127(6) 0.0131(6) 0.0011(4) 0.0045(5) 0.0072(5) O6 0.0227(7) 0.0216(7) 0.0118(6) 0.0015(5) 0.0017(5) 0.0161(6) O7 0.0161(6) 0.0155(6) 0.0110(6) 0.0011(4) 0.0005(4) 0.0099(5) C11 0.0174(8) 0.0137(8) 0.0151(8) 0.0007(6) 0.0004(7) 0.0073(7) C12 0.0143(8) 0.0143(8) 0.0158(8) 0.0007(6) 0.0011(6) 0.0061(7) N11 0.0161(7) 0.0152(7) 0.0116(7) 0.0029(5) 0.0022(5) 0.0092(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 O4 1.453(2) . ? B1 O5 1.456(2) . ? B1 O3 1.486(2) . ? B1 O1 1.497(2) . ? B2 O1 1.351(2) . ? B2 O6 1.359(2) . ? B2 O2 1.400(2) . ? B3 O3 1.337(2) . ? B3 O7 1.378(2) . ? B3 O2 1.396(2) . ? O4 H4 0.8400 . ? O5 H5 0.8400 . ? O6 H6 0.8400 . ? O7 H7 0.8400 . ? C11 N11 1.491(2) . ? C11 C12 1.515(2) 2_666 ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 N11 1.487(2) . ? C12 C11 1.515(2) 2_666 ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? N11 H11C 0.9200 . ? N11 H11D 0.9200 . ? 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 O4 B1 O5 107.42(13) . . ? O4 B1 O3 109.99(14) . . ? O5 B1 O3 108.78(13) . . ? O4 B1 O1 110.12(14) . . ? O5 B1 O1 110.32(13) . . ? O3 B1 O1 110.16(13) . . ? O1 B2 O6 123.75(15) . . ? O1 B2 O2 120.59(15) . . ? O6 B2 O2 115.67(15) . . ? O3 B3 O7 119.22(15) . . ? O3 B3 O2 122.39(15) . . ? O7 B3 O2 118.38(15) . . ? B2 O1 B1 124.38(13) . . ? B3 O2 B2 118.72(13) . . ? B3 O3 B1 123.69(13) . . ? B1 O4 H4 109.5 . . ? B1 O5 H5 109.5 . . ? B2 O6 H6 109.5 . . ? B3 O7 H7 109.5 . . ? N11 C11 C12 110.46(13) . 2_666 ? N11 C11 H11A 109.6 . . ? C12 C11 H11A 109.6 2_666 . ? N11 C11 H11B 109.6 . . ? C12 C11 H11B 109.6 2_666 . ? H11A C11 H11B 108.1 . . ? N11 C12 C11 109.82(14) . 2_666 ? N11 C12 H12A 109.7 . . ? C11 C12 H12A 109.7 2_666 . ? N11 C12 H12B 109.7 . . ? C11 C12 H12B 109.7 2_666 . ? H12A C12 H12B 108.2 . . ? C12 N11 C11 111.59(13) . . ? C12 N11 H11C 109.3 . . ? C11 N11 H11C 109.3 . . ? C12 N11 H11D 109.3 . . ? C11 N11 H11D 109.3 . . ? H11C N11 H11D 108.0 . . ? 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 O4 H4 O7 0.84 2.02 2.8312(17) 162.8 1_455 O5 H5 O7 0.84 2.00 2.8258(16) 169.5 1_565 O6 H6 O1 0.84 1.91 2.7453(16) 176.4 2_567 O7 H7 O2 0.84 1.89 2.7179(16) 167.0 2_657 N11 H11C O4 0.92 1.78 2.6786(18) 163.3 2_566 N11 H11D O5 0.92 1.82 2.7182(19) 165.0 2_666 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.296 _refine_diff_density_min -0.315 _refine_diff_density_rms 0.062 _database_code_depnum_ccdc_archive 'CCDC 930889' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_2c #TrackingRef 'web_deposit_cif_file_0_PeterNHorton_1364203048.borates.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H19 B5 N2 O10' _chemical_formula_weight 333.28 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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 8.8129(2) _cell_length_b 8.8960(2) _cell_length_c 10.3618(2) _cell_angle_alpha 74.0430(10) _cell_angle_beta 78.8540(10) _cell_angle_gamma 88.9620(10) _cell_volume 765.80(3) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3398 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 _exptl_crystal_description 'Cut Block' _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.445 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 348 _exptl_absorpt_coefficient_mu 0.125 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9659 _exptl_absorpt_correction_T_max 0.9779 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; SADABS was used to perform the Absorption correction Estimated minimum and maximum transmission: 0.6778 0.7456 The given Tmin and Tmax were generated using the SHELX SIZE command ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius Roper CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16010 _diffrn_reflns_av_R_equivalents 0.0281 _diffrn_reflns_av_sigmaI/netI 0.0232 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.41 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3493 _reflns_number_gt 3204 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997a)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997b)' _computing_molecular_graphics 'ORTEP3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 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^)+(0.0379P)^2^+0.2418P] 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 3493 _refine_ls_number_parameters 214 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0358 _refine_ls_R_factor_gt 0.0322 _refine_ls_wR_factor_ref 0.0842 _refine_ls_wR_factor_gt 0.0817 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _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 0.09288(12) 0.19162(12) 0.19128(11) 0.0134(2) Uani 1 1 d . . . B2 B -0.09180(13) 0.40610(13) 0.20037(11) 0.0172(2) Uani 1 1 d . . . B3 B -0.09675(12) 0.19512(13) 0.40321(11) 0.0152(2) Uani 1 1 d . . . B4 B 0.37574(13) 0.14403(13) 0.13785(11) 0.0154(2) Uani 1 1 d . . . B5 B 0.20020(13) -0.00021(13) 0.06597(11) 0.0153(2) Uani 1 1 d . . . O1 O 0.02331(8) 0.33840(8) 0.13034(7) 0.01556(15) Uani 1 1 d . . . O2 O -0.15004(9) 0.33765(8) 0.33798(7) 0.02142(17) Uani 1 1 d . . . O3 O 0.01534(8) 0.12295(8) 0.33455(7) 0.01478(15) Uani 1 1 d . . . O4 O 0.25695(8) 0.22491(8) 0.18879(7) 0.01562(15) Uani 1 1 d . . . O5 O 0.34688(8) 0.02105(8) 0.08803(7) 0.01893(16) Uani 1 1 d . . . O6 O 0.07928(8) 0.08214(8) 0.10982(7) 0.01492(15) Uani 1 1 d . . . O7 O -0.15238(10) 0.54300(9) 0.14167(8) 0.0283(2) Uani 1 1 d . . . H7 H -0.1090 0.5751 0.0589 0.042 Uiso 1 1 calc R . . O8 O -0.16079(9) 0.13511(9) 0.53772(7) 0.02095(17) Uani 1 1 d . . . H8 H -0.1156 0.0536 0.5704 0.031 Uiso 1 1 calc R . . O9 O 0.52167(8) 0.19152(9) 0.13694(8) 0.02002(17) Uani 1 1 d . . . H9 H 0.5858 0.1399 0.0971 0.030 Uiso 1 1 calc R . . O10 O 0.18817(8) -0.10555(9) -0.00581(8) 0.01943(16) Uani 1 1 d . . . H10 H 0.1014 -0.0991 -0.0288 0.029 Uiso 1 1 calc R . . C11 C 0.46062(12) 0.25161(12) 0.46816(11) 0.0224(2) Uani 1 1 d . . . H11A H 0.4142 0.1666 0.4419 0.027 Uiso 1 1 calc R . . H11B H 0.5568 0.2136 0.5003 0.027 Uiso 1 1 calc R . . C12 C 0.49852(12) 0.39270(13) 0.34548(11) 0.0229(2) Uani 1 1 d . . . H12A H 0.5476 0.4769 0.3708 0.027 Uiso 1 1 calc R . . H12B H 0.5724 0.3646 0.2715 0.027 Uiso 1 1 calc R . . C13 C 0.23712(14) 0.48246(14) 0.40965(12) 0.0270(2) Uani 1 1 d . . . H13A H 0.1387 0.5116 0.3783 0.032 Uiso 1 1 calc R . . H13B H 0.2755 0.5717 0.4357 0.032 Uiso 1 1 calc R . . C14 C 0.20883(13) 0.34053(14) 0.53237(12) 0.0259(2) Uani 1 1 d . . . H14A H 0.1344 0.3654 0.6077 0.031 Uiso 1 1 calc R . . H14B H 0.1629 0.2538 0.5081 0.031 Uiso 1 1 calc R . . C15 C 0.32145(18) 0.16105(15) 0.70213(13) 0.0366(3) Uani 1 1 d . . . H15A H 0.2724 0.0735 0.6833 0.055 Uiso 1 1 calc R . . H15B H 0.2521 0.1939 0.7747 0.055 Uiso 1 1 calc R . . H15C H 0.4189 0.1281 0.7317 0.055 Uiso 1 1 calc R . . C16 C 0.3869(2) 0.58755(15) 0.17355(13) 0.0408(3) Uani 1 1 d . . . H16A H 0.4284 0.6747 0.1986 0.061 Uiso 1 1 calc R . . H16B H 0.2914 0.6183 0.1396 0.061 Uiso 1 1 calc R . . H16C H 0.4632 0.5605 0.1019 0.061 Uiso 1 1 calc R . . N11 N 0.35268(11) 0.29170(11) 0.57815(9) 0.02153(19) Uani 1 1 d . . . N12 N 0.35315(11) 0.44951(10) 0.29594(9) 0.0217(2) Uani 1 1 d . . . H12 H 0.3118 0.3695 0.2700 0.026 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 0.0141(5) 0.0140(5) 0.0118(5) -0.0041(4) -0.0018(4) 0.0040(4) B2 0.0179(5) 0.0172(5) 0.0145(5) -0.0030(4) -0.0009(4) 0.0050(4) B3 0.0146(5) 0.0169(5) 0.0131(5) -0.0032(4) -0.0019(4) 0.0033(4) B4 0.0164(5) 0.0158(5) 0.0134(5) -0.0035(4) -0.0024(4) 0.0031(4) B5 0.0170(5) 0.0154(5) 0.0130(5) -0.0035(4) -0.0023(4) 0.0038(4) O1 0.0181(3) 0.0151(3) 0.0115(3) -0.0022(3) -0.0007(3) 0.0057(3) O2 0.0246(4) 0.0206(4) 0.0131(3) 0.0003(3) 0.0022(3) 0.0117(3) O3 0.0169(3) 0.0147(3) 0.0110(3) -0.0021(3) -0.0013(3) 0.0051(3) O4 0.0143(3) 0.0171(3) 0.0169(3) -0.0077(3) -0.0022(3) 0.0032(3) O5 0.0153(3) 0.0207(4) 0.0242(4) -0.0122(3) -0.0038(3) 0.0057(3) O6 0.0152(3) 0.0168(3) 0.0140(3) -0.0063(3) -0.0033(2) 0.0042(3) O7 0.0349(5) 0.0242(4) 0.0150(4) 0.0037(3) 0.0060(3) 0.0167(3) O8 0.0223(4) 0.0218(4) 0.0130(3) 0.0009(3) 0.0011(3) 0.0103(3) O9 0.0145(3) 0.0228(4) 0.0252(4) -0.0125(3) -0.0014(3) 0.0036(3) O10 0.0172(3) 0.0228(4) 0.0234(4) -0.0135(3) -0.0063(3) 0.0068(3) C11 0.0220(5) 0.0219(5) 0.0271(6) -0.0106(4) -0.0091(4) 0.0056(4) C12 0.0198(5) 0.0278(6) 0.0232(5) -0.0116(4) -0.0023(4) -0.0027(4) C13 0.0296(6) 0.0282(6) 0.0298(6) -0.0153(5) -0.0123(5) 0.0128(5) C14 0.0198(5) 0.0347(6) 0.0254(5) -0.0136(5) -0.0020(4) 0.0008(4) C15 0.0554(8) 0.0272(6) 0.0247(6) 0.0002(5) -0.0115(6) -0.0086(6) C16 0.0715(10) 0.0223(6) 0.0275(6) 0.0009(5) -0.0174(6) -0.0067(6) N11 0.0248(5) 0.0213(4) 0.0186(4) -0.0046(4) -0.0059(4) -0.0008(3) N12 0.0307(5) 0.0176(4) 0.0189(4) -0.0062(3) -0.0083(4) 0.0006(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag B1 O1 1.4653(12) . ? B1 O3 1.4725(12) . ? B1 O6 1.4734(12) . ? B1 O4 1.4752(12) . ? B2 O7 1.3538(13) . ? B2 O1 1.3609(12) . ? B2 O2 1.3851(13) . ? B3 O8 1.3578(13) . ? B3 O3 1.3604(12) . ? B3 O2 1.3838(13) . ? B4 O9 1.3585(13) . ? B4 O4 1.3638(12) . ? B4 O5 1.3782(13) . ? B5 O6 1.3588(12) . ? B5 O10 1.3637(13) . ? B5 O5 1.3806(13) . ? O7 H7 0.8400 . ? O8 H8 0.8400 . ? O9 H9 0.8400 . ? O10 H10 0.8400 . ? C11 N11 1.4571(14) . ? C11 C12 1.5089(16) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 N12 1.4995(14) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 N12 1.4944(14) . ? C13 C14 1.5097(17) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 N11 1.4561(14) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 N11 1.4597(15) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 N12 1.4886(15) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? N12 H12 0.9300 . ? 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 O3 111.17(7) . . ? O1 B1 O6 108.26(8) . . ? O3 B1 O6 109.99(8) . . ? O1 B1 O4 108.52(8) . . ? O3 B1 O4 108.34(8) . . ? O6 B1 O4 110.56(7) . . ? O7 B2 O1 122.58(9) . . ? O7 B2 O2 116.89(9) . . ? O1 B2 O2 120.52(9) . . ? O8 B3 O3 123.04(9) . . ? O8 B3 O2 116.22(9) . . ? O3 B3 O2 120.73(9) . . ? O9 B4 O4 117.17(9) . . ? O9 B4 O5 122.17(9) . . ? O4 B4 O5 120.65(9) . . ? O6 B5 O10 123.31(9) . . ? O6 B5 O5 121.69(9) . . ? O10 B5 O5 114.97(9) . . ? B2 O1 B1 123.94(8) . . ? B3 O2 B2 119.84(8) . . ? B3 O3 B1 123.55(8) . . ? B4 O4 B1 123.50(8) . . ? B4 O5 B5 118.78(8) . . ? B5 O6 B1 122.66(8) . . ? B2 O7 H7 109.5 . . ? B3 O8 H8 109.5 . . ? B4 O9 H9 109.5 . . ? B5 O10 H10 109.5 . . ? N11 C11 C12 110.29(9) . . ? N11 C11 H11A 109.6 . . ? C12 C11 H11A 109.6 . . ? N11 C11 H11B 109.6 . . ? C12 C11 H11B 109.6 . . ? H11A C11 H11B 108.1 . . ? N12 C12 C11 109.65(9) . . ? N12 C12 H12A 109.7 . . ? C11 C12 H12A 109.7 . . ? N12 C12 H12B 109.7 . . ? C11 C12 H12B 109.7 . . ? H12A C12 H12B 108.2 . . ? N12 C13 C14 110.51(9) . . ? N12 C13 H13A 109.5 . . ? C14 C13 H13A 109.5 . . ? N12 C13 H13B 109.5 . . ? C14 C13 H13B 109.5 . . ? H13A C13 H13B 108.1 . . ? N11 C14 C13 110.81(9) . . ? N11 C14 H14A 109.5 . . ? C13 C14 H14A 109.5 . . ? N11 C14 H14B 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 108.1 . . ? N11 C15 H15A 109.5 . . ? N11 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? N11 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N12 C16 H16A 109.5 . . ? N12 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? N12 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C14 N11 C11 109.32(8) . . ? C14 N11 C15 109.96(10) . . ? C11 N11 C15 111.93(9) . . ? C16 N12 C13 112.35(10) . . ? C16 N12 C12 110.99(10) . . ? C13 N12 C12 110.07(8) . . ? C16 N12 H12 107.7 . . ? C13 N12 H12 107.7 . . ? C12 N12 H12 107.7 . . ? 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 O7 H7 O1 0.84 1.90 2.7422(10) 175.0 2_565 O8 H8 O3 0.84 1.91 2.7466(10) 172.6 2_556 O9 H9 O10 0.84 2.09 2.8508(10) 150.6 2_655 O10 H10 O6 0.84 1.92 2.7570(10) 171.0 2 N12 H12 O4 0.93 1.84 2.7548(11) 169.2 . _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.234 _refine_diff_density_min -0.243 _refine_diff_density_rms 0.040 _database_code_depnum_ccdc_archive 'CCDC 930890' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_2d #TrackingRef 'web_deposit_cif_file_0_PeterNHorton_1364203048.borates.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H28 B10 N2 O20' _chemical_formula_weight 580.42 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.1624(6) _cell_length_b 11.3609(8) _cell_length_c 13.7429(9) _cell_angle_alpha 90.00 _cell_angle_beta 94.416(4) _cell_angle_gamma 90.00 _cell_volume 1270.63(15) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2985 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 _exptl_crystal_description 'Cut Block' _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.517 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 600 _exptl_absorpt_coefficient_mu 0.136 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9450 _exptl_absorpt_correction_T_max 0.9865 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; SADABS was used to perform the Absorption correction Estimated minimum and maximum transmission: 0.6203 0.7456 The given Tmin and Tmax were generated using the SHELX SIZE command ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius Roper CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14949 _diffrn_reflns_av_R_equivalents 0.0486 _diffrn_reflns_av_sigmaI/netI 0.0436 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 27.47 _reflns_number_total 2909 _reflns_number_gt 2153 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997a)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997b)' _computing_molecular_graphics 'ORTEP3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 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^)+(0.0667P)^2^+0.5952P] 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 2909 _refine_ls_number_parameters 187 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0716 _refine_ls_R_factor_gt 0.0481 _refine_ls_wR_factor_ref 0.1328 _refine_ls_wR_factor_gt 0.1194 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _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 0.3547(2) 0.97127(17) 0.28575(14) 0.0176(4) Uani 1 1 d . . . B2 B 0.5371(3) 0.86804(18) 0.17593(14) 0.0206(4) Uani 1 1 d . . . B3 B 0.5190(3) 1.07723(19) 0.16752(14) 0.0202(4) Uani 1 1 d . . . B4 B 0.0616(3) 0.97667(18) 0.32056(15) 0.0208(4) Uani 1 1 d . . . B5 B 0.2643(3) 1.00110(19) 0.45320(15) 0.0220(4) Uani 1 1 d . . . O1 O 0.44207(15) 0.86704(11) 0.25297(8) 0.0202(3) Uani 1 1 d . . . O2 O 0.56401(16) 0.97181(11) 0.12682(9) 0.0215(3) Uani 1 1 d . . . O3 O 0.41926(16) 1.07900(11) 0.24176(9) 0.0216(3) Uani 1 1 d . . . O4 O 0.17840(15) 0.96060(11) 0.25701(9) 0.0216(3) Uani 1 1 d . . . O5 O 0.10257(16) 1.00181(13) 0.41781(9) 0.0283(3) Uani 1 1 d . . . O6 O 0.38503(15) 0.98058(11) 0.39268(9) 0.0188(3) Uani 1 1 d . . . O7 O 0.60769(18) 0.76990(12) 0.14150(10) 0.0288(3) Uani 1 1 d . . . H7 H 0.5918 0.7129 0.1785 0.043 Uiso 1 1 calc R . . O8 O 0.57977(18) 1.17642(11) 0.12815(10) 0.0273(3) Uani 1 1 d . . . H8 H 0.5592 1.2347 0.1628 0.041 Uiso 1 1 calc R . . O9 O -0.10008(16) 0.96851(14) 0.28933(9) 0.0289(3) Uani 1 1 d . . . H9 H -0.1574 0.9734 0.3374 0.043 Uiso 1 1 calc R . . O10 O 0.29610(17) 1.01932(15) 0.55089(9) 0.0326(4) Uani 1 1 d . . . H10 H 0.3981 1.0191 0.5647 0.049 Uiso 1 1 calc R . . C11 C 1.1695(2) 0.96705(17) 0.01246(14) 0.0241(4) Uani 1 1 d . . . H11A H 1.1962 0.9848 0.0824 0.029 Uiso 1 1 calc R . . H11B H 1.2706 0.9373 -0.0145 0.029 Uiso 1 1 calc R . . C12 C 0.8836(2) 0.92123(17) 0.03997(13) 0.0247(4) Uani 1 1 d . . . H12A H 0.9023 0.9376 0.1107 0.030 Uiso 1 1 calc R . . H12B H 0.7945 0.8622 0.0309 0.030 Uiso 1 1 calc R . . C13 C 1.0104(3) 0.82650(18) -0.09939(14) 0.0291(5) Uani 1 1 d . . . H13A H 0.9278 0.7638 -0.1019 0.044 Uiso 1 1 calc R . . H13B H 1.1137 0.7955 -0.1208 0.044 Uiso 1 1 calc R . . H13C H 0.9715 0.8910 -0.1425 0.044 Uiso 1 1 calc R . . C14 C 1.0980(3) 0.77025(19) 0.06739(15) 0.0329(5) Uani 1 1 d . . . H14A H 1.1139 0.7970 0.1353 0.049 Uiso 1 1 calc R . . H14B H 1.2025 0.7412 0.0462 0.049 Uiso 1 1 calc R . . H14C H 1.0165 0.7068 0.0625 0.049 Uiso 1 1 calc R . . N11 N 1.0382(2) 0.87131(13) 0.00335(10) 0.0232(4) 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 0.0188(10) 0.0191(10) 0.0158(9) -0.0007(7) 0.0074(7) -0.0004(8) B2 0.0240(11) 0.0219(10) 0.0170(9) -0.0016(8) 0.0077(8) -0.0004(8) B3 0.0231(10) 0.0212(10) 0.0171(9) -0.0004(8) 0.0068(8) 0.0001(8) B4 0.0231(10) 0.0241(11) 0.0156(9) 0.0009(8) 0.0049(8) -0.0006(8) B5 0.0201(10) 0.0287(11) 0.0179(10) -0.0014(8) 0.0059(8) -0.0004(8) O1 0.0247(7) 0.0179(6) 0.0194(6) 0.0006(5) 0.0110(5) 0.0008(5) O2 0.0285(7) 0.0182(7) 0.0194(6) 0.0013(5) 0.0121(5) 0.0000(5) O3 0.0266(7) 0.0187(7) 0.0211(6) -0.0003(5) 0.0127(5) 0.0005(5) O4 0.0197(7) 0.0311(7) 0.0147(6) -0.0015(5) 0.0056(5) -0.0002(5) O5 0.0175(7) 0.0517(9) 0.0165(7) -0.0050(6) 0.0054(5) 0.0020(6) O6 0.0174(6) 0.0244(7) 0.0152(6) -0.0018(5) 0.0047(5) -0.0002(5) O7 0.0421(9) 0.0183(7) 0.0292(7) 0.0021(6) 0.0230(6) 0.0016(6) O8 0.0389(8) 0.0178(7) 0.0281(7) -0.0005(5) 0.0209(6) 0.0000(6) O9 0.0206(7) 0.0501(9) 0.0164(6) -0.0030(6) 0.0046(5) 0.0000(6) O10 0.0157(7) 0.0650(11) 0.0175(7) -0.0080(6) 0.0043(5) -0.0013(7) C11 0.0217(9) 0.0298(10) 0.0215(9) -0.0010(8) 0.0067(7) -0.0024(8) C12 0.0265(10) 0.0265(10) 0.0225(9) -0.0014(8) 0.0099(8) -0.0041(8) C13 0.0363(12) 0.0293(11) 0.0223(9) -0.0057(8) 0.0057(8) 0.0023(9) C14 0.0435(13) 0.0269(11) 0.0282(10) 0.0043(8) 0.0026(9) 0.0008(9) N11 0.0310(9) 0.0203(8) 0.0194(8) -0.0007(6) 0.0099(6) -0.0008(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag B1 O4 1.467(2) . ? B1 O1 1.471(2) . ? B1 O6 1.475(2) . ? B1 O3 1.480(2) . ? B2 O7 1.357(2) . ? B2 O1 1.360(2) . ? B2 O2 1.384(2) . ? B3 O3 1.353(2) . ? B3 O8 1.360(3) . ? B3 O2 1.383(2) . ? B4 O4 1.354(2) . ? B4 O9 1.359(3) . ? B4 O5 1.382(2) . ? B5 O6 1.358(2) . ? B5 O10 1.363(2) . ? B5 O5 1.371(2) . ? O7 H7 0.8400 . ? O8 H8 0.8400 . ? O9 H9 0.8400 . ? O10 H10 0.8400 . ? C11 C12 1.507(3) 3_775 ? C11 N11 1.525(2) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 N11 1.505(2) . ? C12 C11 1.507(3) 3_775 ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 N11 1.502(2) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 N11 1.505(2) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 B1 O1 109.86(14) . . ? O4 B1 O6 111.11(14) . . ? O1 B1 O6 108.33(14) . . ? O4 B1 O3 109.34(14) . . ? O1 B1 O3 110.12(14) . . ? O6 B1 O3 108.05(14) . . ? O7 B2 O1 123.20(17) . . ? O7 B2 O2 116.26(16) . . ? O1 B2 O2 120.53(17) . . ? O3 B3 O8 123.12(17) . . ? O3 B3 O2 120.77(17) . . ? O8 B3 O2 116.10(16) . . ? O4 B4 O9 120.13(17) . . ? O4 B4 O5 121.42(17) . . ? O9 B4 O5 118.45(17) . . ? O6 B5 O10 122.47(17) . . ? O6 B5 O5 120.54(17) . . ? O10 B5 O5 116.98(17) . . ? B2 O1 B1 123.44(14) . . ? B3 O2 B2 118.89(15) . . ? B3 O3 B1 123.33(14) . . ? B4 O4 B1 122.67(14) . . ? B5 O5 B4 119.77(15) . . ? B5 O6 B1 123.24(14) . . ? B2 O7 H7 109.5 . . ? B3 O8 H8 109.5 . . ? B4 O9 H9 109.5 . . ? B5 O10 H10 109.5 . . ? C12 C11 N11 112.77(16) 3_775 . ? C12 C11 H11A 109.0 3_775 . ? N11 C11 H11A 109.0 . . ? C12 C11 H11B 109.0 3_775 . ? N11 C11 H11B 109.0 . . ? H11A C11 H11B 107.8 . . ? N11 C12 C11 112.04(15) . 3_775 ? N11 C12 H12A 109.2 . . ? C11 C12 H12A 109.2 3_775 . ? N11 C12 H12B 109.2 . . ? C11 C12 H12B 109.2 3_775 . ? H12A C12 H12B 107.9 . . ? N11 C13 H13A 109.5 . . ? N11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N11 C14 H14A 109.5 . . ? N11 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N11 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 N11 C14 108.06(15) . . ? C13 N11 C12 111.84(15) . . ? C14 N11 C12 109.52(15) . . ? C13 N11 C11 111.93(14) . . ? C14 N11 C11 107.59(15) . . ? C12 N11 C11 107.80(14) . . ? 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 O7 H7 O3 0.84 1.88 2.7166(18) 173.3 2_645 O8 H8 O1 0.84 1.90 2.7268(17) 168.8 2_655 O9 H9 O10 0.84 1.98 2.8182(19) 178.2 3_576 O10 H10 O6 0.84 1.82 2.6580(18) 174.4 3_676 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.442 _refine_diff_density_min -0.298 _refine_diff_density_rms 0.062 #===END _database_code_depnum_ccdc_archive 'CCDC 930891'