# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 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_x _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H20 O5, C8 H10 N O2, B F4' _chemical_formula_sum 'C18 H30 B F4 N O7' _chemical_formula_weight 459.24 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.5060(19) _cell_length_b 15.001(3) _cell_length_c 15.777(3) _cell_angle_alpha 90.00 _cell_angle_beta 94.68(3) _cell_angle_gamma 90.00 _cell_volume 2242.3(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1641 _cell_measurement_theta_min 1.88 _cell_measurement_theta_max 25.00 _exptl_crystal_description block _exptl_crystal_colour White _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.360 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 968 _exptl_absorpt_coefficient_mu 0.122 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.971 _exptl_absorpt_correction_T_max 0.988 _exptl_absorpt_process_details 'CrystalClear (Rigaku, 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku SCXmini diffractometer' _diffrn_measurement_method CCD_Profile_fitting _diffrn_detector_area_resol_mean 13.6612 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5946 _diffrn_reflns_av_R_equivalents 0.1011 _diffrn_reflns_av_sigmaI/netI 0.0855 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3959 _reflns_number_gt 1641 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku, 2005)' _computing_cell_refinement 'CrystalClear (Rigaku, 2005)' _computing_data_reduction 'CrystalClear (Rigaku, 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'DIAMOND (Brandenburg & Putz, 2005)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.2000P)^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 3959 _refine_ls_number_parameters 270 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2047 _refine_ls_R_factor_gt 0.1093 _refine_ls_wR_factor_ref 0.3653 _refine_ls_wR_factor_gt 0.2954 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _refine_ls_shift/su_max 0.053 _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 O1 O 0.4579(6) 0.6605(4) 0.5275(3) 0.1035(18) Uani 1 1 d . . . O2 O 0.3241(5) 0.5967(3) 0.6756(3) 0.0816(14) Uani 1 1 d . . . C1 C 0.3890(11) 0.7801(6) 0.4493(6) 0.118 Uani 1 1 d . . . H1A H 0.2927 0.7605 0.4543 0.142 Uiso 1 1 calc R . . H1B H 0.3923 0.8074 0.3937 0.142 Uiso 1 1 calc R . . C2 C 0.4738(10) 0.7080(6) 0.4533(6) 0.109 Uani 1 1 d . . . H2A H 0.4504 0.6701 0.4044 0.131 Uiso 1 1 calc R . . H2B H 0.5713 0.7268 0.4521 0.131 Uiso 1 1 calc R . . O3 O 0.1744(5) 0.7520(3) 0.6904(3) 0.0832(15) Uani 1 1 d . . . C3 C 0.3568(9) 0.5929(7) 0.5247(6) 0.111(3) Uani 1 1 d . . . H3A H 0.3698 0.5530 0.4776 0.133 Uiso 1 1 calc R . . H3B H 0.2629 0.6183 0.5166 0.133 Uiso 1 1 calc R . . O4 O 0.3021(5) 0.9160(3) 0.6650(4) 0.0896(16) Uani 1 1 d . . . C4 C 0.3730(8) 0.5422(5) 0.6070(6) 0.094(3) Uani 1 1 d . . . H4A H 0.4714 0.5266 0.6202 0.113 Uiso 1 1 calc R . . H4B H 0.3186 0.4875 0.6017 0.113 Uiso 1 1 calc R . . O5 O 0.4262(7) 0.8510(5) 0.5174(3) 0.118(2) Uani 1 1 d . . . C5 C 0.1785(8) 0.5963(5) 0.6799(5) 0.093(2) Uani 1 1 d . . . H5A H 0.1494 0.5413 0.7056 0.112 Uiso 1 1 calc R . . H5B H 0.1313 0.6005 0.6232 0.112 Uiso 1 1 calc R . . O6 O 0.2730(6) 0.7832(3) 1.1142(3) 0.0831(15) Uani 1 1 d . . . C6 C 0.1390(8) 0.6752(6) 0.7329(4) 0.084(2) Uani 1 1 d . . . H6A H 0.0386 0.6744 0.7400 0.101 Uiso 1 1 calc R . . H6B H 0.1899 0.6728 0.7887 0.101 Uiso 1 1 calc R . . O7 O 0.3396(5) 0.9217(3) 1.0862(3) 0.0727(13) Uani 1 1 d . . . H7 H 0.2972 0.9326 1.1282 0.109 Uiso 1 1 calc R . . C7 C 0.1292(9) 0.8309(6) 0.7290(5) 0.101(3) Uani 1 1 d . . . H7A H 0.1808 0.8396 0.7839 0.121 Uiso 1 1 calc R . . H7B H 0.0293 0.8275 0.7371 0.121 Uiso 1 1 calc R . . C8 C 0.1572(9) 0.9060(5) 0.6706(7) 0.105(3) Uani 1 1 d . . . H8A H 0.1111 0.8943 0.6146 0.127 Uiso 1 1 calc R . . H8B H 0.1185 0.9608 0.6917 0.127 Uiso 1 1 calc R . . C9 C 0.3382(11) 0.9669(6) 0.5918(7) 0.118(3) Uani 1 1 d . . . H9A H 0.2764 1.0183 0.5855 0.141 Uiso 1 1 calc R . . H9B H 0.4341 0.9887 0.6025 0.141 Uiso 1 1 calc R . . C10 C 0.3277(11) 0.9181(7) 0.5143(6) 0.114(3) Uani 1 1 d . . . H10A H 0.2338 0.8929 0.5046 0.137 Uiso 1 1 calc R . . H10B H 0.3428 0.9579 0.4674 0.137 Uiso 1 1 calc R . . C11 C 0.4461(5) 0.8739(4) 0.9365(3) 0.0493(14) Uani 1 1 d . . . H11 H 0.4426 0.9340 0.9508 0.059 Uiso 1 1 calc R . . C12 C 0.5040(6) 0.8490(4) 0.8638(3) 0.0517(15) Uani 1 1 d . . . H12 H 0.5398 0.8923 0.8293 0.062 Uiso 1 1 calc R . . C13 C 0.5102(6) 0.7600(4) 0.8405(3) 0.0486(14) Uani 1 1 d . . . C14 C 0.4577(6) 0.6960(4) 0.8935(4) 0.0570(16) Uani 1 1 d . . . H14 H 0.4624 0.6360 0.8793 0.068 Uiso 1 1 calc R . . C15 C 0.3991(6) 0.7207(4) 0.9666(4) 0.0545(15) Uani 1 1 d . . . H15 H 0.3635 0.6773 1.0011 0.065 Uiso 1 1 calc R . . C16 C 0.3923(6) 0.8106(4) 0.9897(3) 0.0496(14) Uani 1 1 d . . . C17 C 0.3298(6) 0.8352(5) 1.0685(4) 0.0581(16) Uani 1 1 d . . . F1 F 0.6453(5) 0.5058(4) 0.8360(3) 0.1163(17) Uani 1 1 d . . . F2 F 0.8132(9) 0.5492(4) 0.7596(5) 0.188(3) Uani 1 1 d . . . F3 F 0.8303(7) 0.4272(4) 0.8186(4) 0.153(2) Uani 1 1 d . . . F4 F 0.6824(6) 0.4420(7) 0.7115(4) 0.205(4) Uani 1 1 d . . . B B 0.7388(7) 0.4795(5) 0.7813(4) 0.0564(18) Uani 1 1 d . . . N1 N 0.4984(5) 0.7650(3) 0.6837(3) 0.0476(12) Uani 1 1 d . . . H1C H 0.4141 0.7389 0.6770 0.071 Uiso 1 1 calc R . . H1D H 0.5468 0.7526 0.6392 0.071 Uiso 1 1 calc R . . H1E H 0.4873 0.8237 0.6876 0.071 Uiso 1 1 calc R . . C18 C 0.5753(7) 0.7318(4) 0.7611(4) 0.0631(17) Uani 1 1 d . . . H18A H 0.6717 0.7534 0.7635 0.076 Uiso 1 1 calc R . . H18B H 0.5782 0.6672 0.7589 0.076 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 O1 0.129(5) 0.115(4) 0.064(3) -0.021(3) -0.006(3) -0.021(4) O2 0.072(3) 0.081(3) 0.087(3) 0.001(3) -0.015(3) -0.002(3) C1 0.118 0.118 0.118 0.000 0.010 0.000 C2 0.109 0.109 0.109 0.000 0.009 0.000 O3 0.077(3) 0.091(3) 0.084(3) -0.004(3) 0.019(3) 0.001(3) C3 0.087(5) 0.148(8) 0.096(6) -0.054(6) -0.009(5) 0.001(6) O4 0.081(3) 0.076(3) 0.110(4) 0.000(3) 0.000(3) 0.009(3) C4 0.071(5) 0.065(5) 0.142(8) -0.038(5) -0.016(5) 0.001(4) O5 0.147(5) 0.127(5) 0.075(4) 0.026(4) -0.014(3) 0.014(4) C5 0.084(5) 0.091(6) 0.104(6) 0.006(5) 0.001(5) -0.023(5) O6 0.106(4) 0.086(3) 0.061(3) -0.002(3) 0.031(3) -0.013(3) C6 0.077(5) 0.113(6) 0.062(4) 0.009(5) 0.005(4) -0.009(5) O7 0.094(3) 0.062(3) 0.065(3) -0.016(2) 0.027(2) -0.002(3) C7 0.091(6) 0.115(7) 0.102(6) -0.009(6) 0.042(5) 0.026(5) C8 0.088(6) 0.077(5) 0.152(8) -0.004(6) 0.012(6) 0.040(5) C9 0.121(7) 0.095(7) 0.132(9) 0.025(7) -0.018(6) 0.013(6) C10 0.119(7) 0.122(8) 0.095(7) 0.047(6) -0.034(5) -0.003(6) C11 0.053(3) 0.054(3) 0.041(3) -0.002(3) 0.005(2) -0.006(3) C12 0.063(4) 0.050(3) 0.042(3) 0.002(3) 0.002(3) 0.001(3) C13 0.047(3) 0.062(4) 0.035(3) 0.006(3) -0.009(2) 0.009(3) C14 0.055(3) 0.051(3) 0.063(4) -0.005(3) -0.003(3) 0.009(3) C15 0.052(3) 0.067(4) 0.044(3) 0.004(3) 0.007(3) -0.004(3) C16 0.051(3) 0.052(3) 0.044(3) -0.002(3) -0.005(3) 0.002(3) C17 0.048(3) 0.070(4) 0.055(4) -0.002(3) -0.003(3) 0.000(3) F1 0.087(3) 0.167(5) 0.098(3) -0.042(3) 0.028(2) 0.010(3) F2 0.272(8) 0.138(5) 0.168(6) 0.015(4) 0.108(6) -0.049(5) F3 0.178(5) 0.144(4) 0.131(5) 0.005(4) -0.023(4) 0.096(4) F4 0.095(4) 0.394(11) 0.121(4) -0.133(6) -0.026(3) 0.025(5) B 0.051(4) 0.072(5) 0.045(4) 0.002(4) -0.002(3) 0.003(4) N1 0.056(3) 0.045(3) 0.041(3) -0.008(2) -0.001(2) 0.004(2) C18 0.065(4) 0.078(4) 0.045(3) 0.000(3) 0.002(3) 0.029(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C2 1.389(10) . ? O1 C3 1.396(10) . ? O2 C5 1.391(8) . ? O2 C4 1.462(9) . ? C1 C2 1.347(12) . ? C1 O5 1.532(10) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? O3 C6 1.389(8) . ? O3 C7 1.413(9) . ? C3 C4 1.501(12) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? O4 C8 1.395(9) . ? O4 C9 1.448(11) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? O5 C10 1.374(11) . ? C5 C6 1.513(10) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? O6 C17 1.219(7) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? O7 C17 1.329(7) . ? O7 H7 0.8200 . ? C7 C8 1.493(11) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.422(13) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C16 1.392(8) . ? C11 C12 1.365(7) . ? C11 H11 0.9300 . ? C12 C13 1.387(8) . ? C12 H12 0.9300 . ? C13 C14 1.392(8) . ? C13 C18 1.503(8) . ? C14 C15 1.372(8) . ? C14 H14 0.9300 . ? C15 C16 1.399(8) . ? C15 H15 0.9300 . ? C16 C17 1.468(8) . ? F1 B 1.347(8) . ? F2 B 1.323(9) . ? F3 B 1.278(8) . ? F4 B 1.312(8) . ? N1 C18 1.459(7) . ? N1 H1C 0.8900 . ? N1 H1D 0.8900 . ? N1 H1E 0.8900 . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? 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 O1 C3 117.9(7) . . ? C5 O2 C4 114.3(5) . . ? C2 C1 O5 114.8(9) . . ? C2 C1 H1A 108.6 . . ? O5 C1 H1A 108.6 . . ? C2 C1 H1B 108.6 . . ? O5 C1 H1B 108.6 . . ? H1A C1 H1B 107.5 . . ? O1 C2 C1 110.2(8) . . ? O1 C2 H2A 109.6 . . ? C1 C2 H2A 109.6 . . ? O1 C2 H2B 109.6 . . ? C1 C2 H2B 109.6 . . ? H2A C2 H2B 108.1 . . ? C6 O3 C7 113.2(6) . . ? O1 C3 C4 108.6(7) . . ? O1 C3 H3A 110.0 . . ? C4 C3 H3A 110.0 . . ? O1 C3 H3B 110.0 . . ? C4 C3 H3B 110.0 . . ? H3A C3 H3B 108.4 . . ? C8 O4 C9 114.0(7) . . ? C3 C4 O2 109.9(6) . . ? C3 C4 H4A 109.7 . . ? O2 C4 H4A 109.7 . . ? C3 C4 H4B 109.7 . . ? O2 C4 H4B 109.7 . . ? H4A C4 H4B 108.2 . . ? C10 O5 C1 111.5(7) . . ? O2 C5 C6 108.4(6) . . ? O2 C5 H5A 110.0 . . ? C6 C5 H5A 110.0 . . ? O2 C5 H5B 110.0 . . ? C6 C5 H5B 110.0 . . ? H5A C5 H5B 108.4 . . ? O3 C6 C5 107.6(6) . . ? O3 C6 H6A 110.2 . . ? C5 C6 H6A 110.2 . . ? O3 C6 H6B 110.2 . . ? C5 C6 H6B 110.2 . . ? H6A C6 H6B 108.5 . . ? C17 O7 H7 109.5 . . ? O3 C7 C8 106.9(6) . . ? O3 C7 H7A 110.3 . . ? C8 C7 H7A 110.3 . . ? O3 C7 H7B 110.3 . . ? C8 C7 H7B 110.3 . . ? H7A C7 H7B 108.6 . . ? O4 C8 C7 110.3(7) . . ? O4 C8 H8A 109.6 . . ? C7 C8 H8A 109.6 . . ? O4 C8 H8B 109.6 . . ? C7 C8 H8B 109.6 . . ? H8A C8 H8B 108.1 . . ? C10 C9 O4 114.2(8) . . ? C10 C9 H9A 108.7 . . ? O4 C9 H9A 108.7 . . ? C10 C9 H9B 108.7 . . ? O4 C9 H9B 108.7 . . ? H9A C9 H9B 107.6 . . ? O5 C10 C9 110.3(7) . . ? O5 C10 H10A 109.6 . . ? C9 C10 H10A 109.6 . . ? O5 C10 H10B 109.6 . . ? C9 C10 H10B 109.6 . . ? H10A C10 H10B 108.1 . . ? C16 C11 C12 120.8(5) . . ? C16 C11 H11 119.6 . . ? C12 C11 H11 119.6 . . ? C13 C12 C11 121.0(5) . . ? C13 C12 H12 119.5 . . ? C11 C12 H12 119.5 . . ? C14 C13 C12 118.7(5) . . ? C14 C13 C18 119.9(5) . . ? C12 C13 C18 121.4(5) . . ? C15 C14 C13 120.6(6) . . ? C15 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? C14 C15 C16 120.6(6) . . ? C14 C15 H15 119.7 . . ? C16 C15 H15 119.7 . . ? C11 C16 C15 118.3(5) . . ? C11 C16 C17 122.1(5) . . ? C15 C16 C17 119.6(5) . . ? O6 C17 O7 121.8(6) . . ? O6 C17 C16 124.7(6) . . ? O7 C17 C16 113.4(6) . . ? F3 B F4 109.8(7) . . ? F3 B F2 104.3(7) . . ? F4 B F2 108.1(7) . . ? F3 B F1 110.2(6) . . ? F4 B F1 114.6(6) . . ? F2 B F1 109.2(7) . . ? C18 N1 H1C 109.5 . . ? C18 N1 H1D 109.5 . . ? H1C N1 H1D 109.5 . . ? C18 N1 H1E 109.5 . . ? H1C N1 H1E 109.5 . . ? H1D N1 H1E 109.5 . . ? N1 C18 C13 112.9(5) . . ? N1 C18 H18A 109.0 . . ? C13 C18 H18A 109.0 . . ? N1 C18 H18B 109.0 . . ? C13 C18 H18B 109.0 . . ? H18A C18 H18B 107.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 O1 C2 C1 90.8(10) . . . . ? O5 C1 C2 O1 66.1(11) . . . . ? C2 O1 C3 C4 171.6(7) . . . . ? O1 C3 C4 O2 71.8(8) . . . . ? C5 O2 C4 C3 81.3(8) . . . . ? C2 C1 O5 C10 -174.2(9) . . . . ? C4 O2 C5 C6 -162.3(6) . . . . ? C7 O3 C6 C5 173.7(6) . . . . ? O2 C5 C6 O3 63.5(8) . . . . ? C6 O3 C7 C8 -172.6(6) . . . . ? C9 O4 C8 C7 161.9(7) . . . . ? O3 C7 C8 O4 -65.3(9) . . . . ? C8 O4 C9 C10 -78.5(10) . . . . ? C1 O5 C10 C9 161.8(8) . . . . ? O4 C9 C10 O5 -65.7(11) . . . . ? C16 C11 C12 C13 0.3(8) . . . . ? C11 C12 C13 C14 -0.8(8) . . . . ? C11 C12 C13 C18 -179.3(5) . . . . ? C12 C13 C14 C15 1.0(8) . . . . ? C18 C13 C14 C15 179.5(5) . . . . ? C13 C14 C15 C16 -0.7(8) . . . . ? C12 C11 C16 C15 0.0(8) . . . . ? C12 C11 C16 C17 179.8(5) . . . . ? C14 C15 C16 C11 0.2(8) . . . . ? C14 C15 C16 C17 -179.7(5) . . . . ? C11 C16 C17 O6 175.0(6) . . . . ? C15 C16 C17 O6 -5.3(9) . . . . ? C11 C16 C17 O7 -4.6(8) . . . . ? C15 C16 C17 O7 175.2(5) . . . . ? C14 C13 C18 N1 117.1(6) . . . . ? C12 C13 C18 N1 -64.4(7) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.497 _refine_diff_density_min -0.436 _refine_diff_density_rms 0.074 _database_code_depnum_ccdc_archive 'CCDC 946942' ####################################################################### # # 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_x _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H20 O5, C8 H10 N O2, Cl O4' _chemical_formula_sum 'C18 H30 Cl N O11' _chemical_formula_weight 471.88 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.5970(19) _cell_length_b 15.241(3) _cell_length_c 15.677(3) _cell_angle_alpha 90.00 _cell_angle_beta 93.90(3) _cell_angle_gamma 90.00 _cell_volume 2287.7(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2129 _cell_measurement_theta_min 1.87 _cell_measurement_theta_max 25.40 _exptl_crystal_description Prism _exptl_crystal_colour White _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.370 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1000 _exptl_absorpt_coefficient_mu 0.224 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.948 _exptl_absorpt_correction_T_max 0.967 _exptl_absorpt_process_details 'CrystalClear (Rigaku, 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku SCXmini diffractometer' _diffrn_measurement_method CCD_Profile_fitting _diffrn_detector_area_resol_mean 13.6612 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6308 _diffrn_reflns_av_R_equivalents 0.1206 _diffrn_reflns_av_sigmaI/netI 0.0800 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 25.40 _reflns_number_total 4212 _reflns_number_gt 2129 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku, 2005)' _computing_cell_refinement 'CrystalClear (Rigaku, 2005)' _computing_data_reduction 'CrystalClear (Rigaku, 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'DIAMOND (Brandenburg & Putz, 2005)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.1639P)^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 4212 _refine_ls_number_parameters 281 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1668 _refine_ls_R_factor_gt 0.0945 _refine_ls_wR_factor_ref 0.3006 _refine_ls_wR_factor_gt 0.2513 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl Cl 0.23635(13) 0.47309(10) 0.79021(8) 0.0578(5) Uani 1 1 d . . . O1 O 0.0730(7) 0.1691(5) 0.4820(4) 0.138(2) Uani 1 1 d . . . C1 C 0.1650(13) 0.0973(9) 0.4872(7) 0.148(4) Uani 1 1 d . . . H1A H 0.1398 0.0594 0.5334 0.177 Uiso 1 1 calc R . . H1B H 0.2588 0.1189 0.5016 0.177 Uiso 1 1 calc R . . O2 O 0.1977(5) 0.0952(4) 0.3359(4) 0.1052(17) Uani 1 1 d . . . C2 C 0.1663(12) 0.0454(7) 0.4095(9) 0.143(4) Uani 1 1 d . . . H2A H 0.2350 -0.0010 0.4182 0.171 Uiso 1 1 calc R . . H2B H 0.0756 0.0180 0.3986 0.171 Uiso 1 1 calc R . . O3 O 0.3270(5) 0.2556(4) 0.3060(3) 0.1018(17) Uani 1 1 d . . . C3 C 0.3388(9) 0.1044(6) 0.3262(7) 0.115(3) Uani 1 1 d . . . H3A H 0.3744 0.0504 0.3031 0.138 Uiso 1 1 calc R . . H3B H 0.3871 0.1142 0.3817 0.138 Uiso 1 1 calc R . . O4 O 0.1802(5) 0.4097(3) 0.3180(3) 0.0894(15) Uani 1 1 d . . . C4 C 0.3681(9) 0.1767(7) 0.2698(6) 0.121(3) Uani 1 1 d . . . H4A H 0.4672 0.1785 0.2613 0.145 Uiso 1 1 calc R . . H4B H 0.3179 0.1683 0.2146 0.145 Uiso 1 1 calc R . . O5 O 0.0440(7) 0.3532(5) 0.4678(4) 0.120(2) Uani 1 1 d . . . C5 C 0.3621(7) 0.3320(6) 0.2604(5) 0.092(2) Uani 1 1 d . . . H5A H 0.3105 0.3338 0.2050 0.110 Uiso 1 1 calc R . . H5B H 0.4612 0.3328 0.2517 0.110 Uiso 1 1 calc R . . O6 O 0.6596(5) 0.4273(3) 0.4090(3) 0.0787(13) Uani 1 1 d . . . H6C H 0.6630 0.4358 0.3575 0.118 Uiso 1 1 calc R . . C6 C 0.3241(8) 0.4077(5) 0.3134(6) 0.100(2) Uani 1 1 d . . . H6A H 0.3694 0.4024 0.3704 0.120 Uiso 1 1 calc R . . H6B H 0.3555 0.4618 0.2883 0.120 Uiso 1 1 calc R . . O7 O 0.7337(5) 0.2932(3) 0.3793(3) 0.0889(14) Uani 1 1 d . . . C7 C 0.1327(9) 0.4608(5) 0.3851(8) 0.119(3) Uani 1 1 d . . . H7A H 0.0365 0.4777 0.3707 0.142 Uiso 1 1 calc R . . H7B H 0.1881 0.5140 0.3905 0.142 Uiso 1 1 calc R . . N1 N 0.5077(4) 0.2534(3) 0.8119(2) 0.0482(10) Uani 1 1 d . . . H1C H 0.5989 0.2501 0.8054 0.072 Uiso 1 1 calc R . . H1D H 0.4860 0.2182 0.8543 0.072 Uiso 1 1 calc R . . H1E H 0.4853 0.3084 0.8243 0.072 Uiso 1 1 calc R . . C8 C 0.1417(10) 0.4117(9) 0.4728(7) 0.138(4) Uani 1 1 d . . . H8B H 0.2324 0.3840 0.4831 0.165 Uiso 1 1 calc R . . H8C H 0.1279 0.4523 0.5191 0.165 Uiso 1 1 calc R . . O9 O 0.3241(13) 0.4159(6) 0.8297(7) 0.240(5) Uani 1 1 d . . . C9 C 0.0236(13) 0.3028(9) 0.5425(7) 0.147(4) Uani 1 1 d . . . H9A H -0.0727 0.2832 0.5406 0.176 Uiso 1 1 calc R . . H9B H 0.0399 0.3399 0.5924 0.176 Uiso 1 1 calc R . . O10 O 0.1806(7) 0.4420(8) 0.7151(4) 0.231(6) Uani 1 1 d . . . C10 C 0.1129(12) 0.2288(10) 0.5508(6) 0.157(5) Uani 1 1 d . . . H10A H 0.2094 0.2468 0.5476 0.188 Uiso 1 1 calc R . . H10B H 0.1036 0.2005 0.6055 0.188 Uiso 1 1 calc R . . C11 C 0.6097(5) 0.2261(4) 0.5242(3) 0.0553(14) Uani 1 1 d . . . H11A H 0.6479 0.1852 0.4885 0.066 Uiso 1 1 calc R . . O11 O 0.3286(9) 0.5409(5) 0.7727(5) 0.181(3) Uani 1 1 d . . . O12 O 0.1392(6) 0.4985(5) 0.8476(4) 0.130(2) Uani 1 1 d . . . C12 C 0.5515(5) 0.1985(4) 0.5977(3) 0.0555(13) Uani 1 1 d . . . H12B H 0.5500 0.1389 0.6101 0.067 Uiso 1 1 calc R . . C13 C 0.4958(5) 0.2565(3) 0.6532(3) 0.0443(12) Uani 1 1 d . . . C14 C 0.4964(5) 0.3452(4) 0.6322(3) 0.0547(13) Uani 1 1 d . . . H14A H 0.4575 0.3856 0.6683 0.066 Uiso 1 1 calc R . . C15 C 0.5535(5) 0.3743(3) 0.5591(3) 0.0491(12) Uani 1 1 d . . . H15A H 0.5540 0.4339 0.5463 0.059 Uiso 1 1 calc R . . C16 C 0.6113(4) 0.3134(3) 0.5038(3) 0.0444(12) Uani 1 1 d . . . C17 C 0.6752(5) 0.3435(4) 0.4251(3) 0.0551(14) Uani 1 1 d . . . C18 C 0.4310(6) 0.2267(4) 0.7334(3) 0.0620(15) Uani 1 1 d . . . H18A H 0.3369 0.2500 0.7330 0.074 Uiso 1 1 calc R . . H18B H 0.4242 0.1632 0.7326 0.074 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 Cl 0.0464(7) 0.0772(10) 0.0499(7) 0.0059(7) 0.0023(5) 0.0039(7) O1 0.155(6) 0.175(7) 0.078(4) 0.034(4) -0.027(4) 0.018(5) C1 0.164(11) 0.171(11) 0.104(8) 0.064(8) -0.017(7) -0.004(9) O2 0.076(3) 0.090(3) 0.146(5) -0.010(4) -0.016(3) 0.000(3) C2 0.128(8) 0.131(9) 0.163(10) 0.055(9) -0.035(8) -0.005(6) O3 0.074(3) 0.121(4) 0.113(4) -0.016(3) 0.026(3) 0.006(3) C3 0.079(6) 0.118(7) 0.149(8) -0.014(6) 0.008(6) 0.022(5) O4 0.057(3) 0.095(3) 0.113(4) 0.006(3) -0.016(3) -0.013(2) C4 0.088(6) 0.167(9) 0.110(6) -0.021(7) 0.027(5) 0.052(6) O5 0.120(5) 0.163(6) 0.077(4) -0.044(4) -0.001(3) -0.014(4) C5 0.063(4) 0.130(7) 0.085(5) 0.008(5) 0.023(4) -0.014(4) O6 0.093(3) 0.084(3) 0.062(2) 0.016(2) 0.027(2) 0.012(2) C6 0.084(5) 0.105(6) 0.109(6) 0.010(5) -0.002(5) -0.030(4) O7 0.099(3) 0.108(3) 0.065(3) 0.001(3) 0.040(3) 0.021(3) C7 0.085(6) 0.080(5) 0.188(11) -0.050(7) -0.009(6) 0.006(4) N1 0.040(2) 0.070(3) 0.034(2) 0.0046(19) -0.0015(17) 0.0018(19) C8 0.082(6) 0.195(11) 0.133(9) -0.087(9) -0.016(6) 0.004(7) O9 0.323(13) 0.189(8) 0.198(9) -0.020(7) -0.054(9) 0.165(9) C9 0.142(9) 0.206(12) 0.094(7) -0.006(8) 0.012(6) 0.019(9) O10 0.084(4) 0.509(17) 0.100(4) -0.142(7) 0.005(3) -0.021(6) C10 0.138(9) 0.262(15) 0.069(6) 0.001(8) -0.008(6) 0.036(9) C11 0.055(3) 0.062(4) 0.050(3) -0.002(3) 0.011(3) 0.017(3) O11 0.245(9) 0.163(6) 0.146(6) 0.015(5) 0.093(6) -0.083(6) O12 0.095(4) 0.175(6) 0.125(5) -0.060(4) 0.042(4) -0.014(4) C12 0.053(3) 0.056(3) 0.057(3) 0.003(3) -0.004(2) -0.007(3) C13 0.036(3) 0.059(3) 0.037(2) 0.000(2) 0.000(2) -0.016(2) C14 0.055(3) 0.070(4) 0.039(3) -0.011(3) 0.006(2) 0.000(3) C15 0.043(3) 0.059(3) 0.045(3) -0.002(2) 0.007(2) 0.003(2) C16 0.030(2) 0.065(3) 0.037(2) -0.001(2) -0.0013(19) 0.003(2) C17 0.039(3) 0.076(4) 0.050(3) 0.006(3) 0.006(2) 0.006(3) C18 0.053(3) 0.084(4) 0.047(3) 0.006(3) -0.003(2) -0.024(3) _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 Cl O9 1.335(8) . ? Cl O10 1.346(6) . ? Cl O12 1.394(5) . ? Cl O11 1.400(6) . ? O1 C1 1.405(13) . ? O1 C10 1.443(12) . ? C1 C2 1.454(15) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? O2 C3 1.380(9) . ? O2 C2 1.429(12) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? O3 C4 1.398(9) . ? O3 C5 1.419(8) . ? C3 C4 1.452(12) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? O4 C6 1.388(8) . ? O4 C7 1.409(10) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? O5 C8 1.292(11) . ? O5 C9 1.424(12) . ? C5 C6 1.482(10) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? O6 C17 1.309(7) . ? O6 H6C 0.8200 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? O7 C17 1.213(6) . ? C7 C8 1.564(14) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? N1 C18 1.449(6) . ? N1 H1C 0.8900 . ? N1 H1D 0.8900 . ? N1 H1E 0.8900 . ? C8 H8B 0.9700 . ? C8 H8C 0.9700 . ? C9 C10 1.417(14) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C16 1.369(7) . ? C11 C12 1.379(7) . ? C11 H11A 0.9300 . ? C12 C13 1.373(7) . ? C12 H12B 0.9300 . ? C13 C14 1.390(7) . ? C13 C18 1.511(7) . ? C14 C15 1.377(7) . ? C14 H14A 0.9300 . ? C15 C16 1.410(7) . ? C15 H15A 0.9300 . ? C16 C17 1.487(7) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? 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 O9 Cl O10 112.1(7) . . ? O9 Cl O12 108.1(6) . . ? O10 Cl O12 114.8(4) . . ? O9 Cl O11 100.7(7) . . ? O10 Cl O11 107.9(6) . . ? O12 Cl O11 112.4(4) . . ? C1 O1 C10 108.3(9) . . ? O1 C1 C2 114.6(9) . . ? O1 C1 H1A 108.6 . . ? C2 C1 H1A 108.6 . . ? O1 C1 H1B 108.6 . . ? C2 C1 H1B 108.6 . . ? H1A C1 H1B 107.6 . . ? C3 O2 C2 113.9(8) . . ? O2 C2 C1 113.7(9) . . ? O2 C2 H2A 108.8 . . ? C1 C2 H2A 108.8 . . ? O2 C2 H2B 108.8 . . ? C1 C2 H2B 108.8 . . ? H2A C2 H2B 107.7 . . ? C4 O3 C5 114.7(6) . . ? O2 C3 C4 112.1(8) . . ? O2 C3 H3A 109.2 . . ? C4 C3 H3A 109.2 . . ? O2 C3 H3B 109.2 . . ? C4 C3 H3B 109.2 . . ? H3A C3 H3B 107.9 . . ? C6 O4 C7 115.1(6) . . ? O3 C4 C3 109.5(7) . . ? O3 C4 H4A 109.8 . . ? C3 C4 H4A 109.8 . . ? O3 C4 H4B 109.8 . . ? C3 C4 H4B 109.8 . . ? H4A C4 H4B 108.2 . . ? C8 O5 C9 117.5(9) . . ? O3 C5 C6 106.2(5) . . ? O3 C5 H5A 110.5 . . ? C6 C5 H5A 110.5 . . ? O3 C5 H5B 110.5 . . ? C6 C5 H5B 110.5 . . ? H5A C5 H5B 108.7 . . ? C17 O6 H6C 109.5 . . ? O4 C6 C5 109.2(6) . . ? O4 C6 H6A 109.8 . . ? C5 C6 H6A 109.8 . . ? O4 C6 H6B 109.8 . . ? C5 C6 H6B 109.8 . . ? H6A C6 H6B 108.3 . . ? O4 C7 C8 113.0(7) . . ? O4 C7 H7A 109.0 . . ? C8 C7 H7A 109.0 . . ? O4 C7 H7B 109.0 . . ? C8 C7 H7B 109.0 . . ? H7A C7 H7B 107.8 . . ? C18 N1 H1C 109.5 . . ? C18 N1 H1D 109.5 . . ? H1C N1 H1D 109.5 . . ? C18 N1 H1E 109.5 . . ? H1C N1 H1E 109.5 . . ? H1D N1 H1E 109.5 . . ? O5 C8 C7 106.3(8) . . ? O5 C8 H8B 110.5 . . ? C7 C8 H8B 110.5 . . ? O5 C8 H8C 110.5 . . ? C7 C8 H8C 110.5 . . ? H8B C8 H8C 108.7 . . ? O5 C9 C10 112.9(9) . . ? O5 C9 H9A 109.0 . . ? C10 C9 H9A 109.0 . . ? O5 C9 H9B 109.0 . . ? C10 C9 H9B 109.0 . . ? H9A C9 H9B 107.8 . . ? O1 C10 C9 107.8(9) . . ? O1 C10 H10A 110.2 . . ? C9 C10 H10A 110.2 . . ? O1 C10 H10B 110.2 . . ? C9 C10 H10B 110.2 . . ? H10A C10 H10B 108.5 . . ? C16 C11 C12 120.2(5) . . ? C16 C11 H11A 119.9 . . ? C12 C11 H11A 119.9 . . ? C13 C12 C11 122.0(5) . . ? C13 C12 H12B 119.0 . . ? C11 C12 H12B 119.0 . . ? C12 C13 C14 117.9(4) . . ? C12 C13 C18 122.2(5) . . ? C14 C13 C18 119.8(5) . . ? C15 C14 C13 121.1(5) . . ? C15 C14 H14A 119.4 . . ? C13 C14 H14A 119.4 . . ? C14 C15 C16 119.7(5) . . ? C14 C15 H15A 120.1 . . ? C16 C15 H15A 120.1 . . ? C11 C16 C15 119.0(4) . . ? C11 C16 C17 120.4(5) . . ? C15 C16 C17 120.6(5) . . ? O7 C17 O6 123.6(5) . . ? O7 C17 C16 122.0(5) . . ? O6 C17 C16 114.4(5) . . ? N1 C18 C13 114.1(4) . . ? N1 C18 H18A 108.7 . . ? C13 C18 H18A 108.7 . . ? N1 C18 H18B 108.7 . . ? C13 C18 H18B 108.7 . . ? H18A C18 H18B 107.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C10 O1 C1 C2 -162.3(10) . . . . ? C3 O2 C2 C1 85.8(11) . . . . ? O1 C1 C2 O2 56.4(13) . . . . ? C2 O2 C3 C4 -161.1(9) . . . . ? C5 O3 C4 C3 174.5(7) . . . . ? O2 C3 C4 O3 63.4(10) . . . . ? C4 O3 C5 C6 -173.9(6) . . . . ? C7 O4 C6 C5 162.1(7) . . . . ? O3 C5 C6 O4 -65.8(8) . . . . ? C6 O4 C7 C8 -81.3(8) . . . . ? C9 O5 C8 C7 -175.8(8) . . . . ? O4 C7 C8 O5 -72.5(9) . . . . ? C8 O5 C9 C10 -85.2(13) . . . . ? C1 O1 C10 C9 177.3(10) . . . . ? O5 C9 C10 O1 -66.6(14) . . . . ? C16 C11 C12 C13 -1.0(8) . . . . ? C11 C12 C13 C14 1.4(7) . . . . ? C11 C12 C13 C18 179.5(5) . . . . ? C12 C13 C14 C15 -1.3(7) . . . . ? C18 C13 C14 C15 -179.4(5) . . . . ? C13 C14 C15 C16 0.7(7) . . . . ? C12 C11 C16 C15 0.3(7) . . . . ? C12 C11 C16 C17 179.3(5) . . . . ? C14 C15 C16 C11 -0.2(7) . . . . ? C14 C15 C16 C17 -179.2(4) . . . . ? C11 C16 C17 O7 -3.9(8) . . . . ? C15 C16 C17 O7 175.1(5) . . . . ? C11 C16 C17 O6 174.5(5) . . . . ? C15 C16 C17 O6 -6.5(7) . . . . ? C12 C13 C18 N1 113.1(5) . . . . ? C14 C13 C18 N1 -68.8(7) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.40 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.457 _refine_diff_density_min -0.311 _refine_diff_density_rms 0.078 _database_code_depnum_ccdc_archive 'CCDC 946943' ####################################################################### # # 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_x _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H24 O6, C8 H10 N O2, B F4' _chemical_formula_sum 'C20 H34 B F4 N O8' _chemical_formula_weight 503.29 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' F F 0.0171 0.0103 '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 _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 23.270(5) _cell_length_b 12.926(3) _cell_length_c 19.947(4) _cell_angle_alpha 90.00 _cell_angle_beta 117.76(3) _cell_angle_gamma 90.00 _cell_volume 5309(2) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9 _cell_measurement_theta_max 12 _exptl_crystal_description Prism _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.259 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2128 _exptl_absorpt_coefficient_mu 0.112 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.973 _exptl_absorpt_correction_T_max 0.989 _exptl_absorpt_process_details '(North, Phillips & MATHEWS,1968)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'NONIUS CAD4' _diffrn_measurement_method \w/2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time 2h _diffrn_standards_decay_% 1 _diffrn_reflns_number 4882 _diffrn_reflns_av_R_equivalents 0.2798 _diffrn_reflns_av_sigmaI/netI 0.0532 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 25.43 _reflns_number_total 4881 _reflns_number_gt 2011 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku, 2005)' _computing_cell_refinement 'CrystalClear (Rigaku, 2005)' _computing_data_reduction 'CrystalClear (Rigaku, 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND (Brandenburg & Putz, 2005)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.1004P)^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 4881 _refine_ls_number_parameters 344 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1684 _refine_ls_R_factor_gt 0.0805 _refine_ls_wR_factor_ref 0.2333 _refine_ls_wR_factor_gt 0.1885 _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 O1 O 0.05557(16) 0.3105(2) 0.19919(16) 0.1107(10) Uani 1 1 d . . . H1D H 0.0438 0.3384 0.1561 0.133 Uiso 1 1 d R . . O3 O 0.09097(15) 0.0605(2) -0.0031(2) 0.1094(10) Uani 1 1 d . . . O4 O 0.1922(2) 0.0497(2) 0.14873(18) 0.1106(10) Uani 1 1 d . . . O5 O 0.32052(18) 0.0176(2) 0.18228(18) 0.1194(11) Uani 1 1 d . . . O6 O 0.35383(18) 0.0876(3) 0.0744(3) 0.1307(12) Uani 1 1 d . . . O8 O 0.12907(19) 0.1327(2) -0.10852(17) 0.1157(11) Uani 1 1 d . . . O7 O 0.2621(2) 0.1139(2) -0.0771(2) 0.1174(11) Uani 1 1 d . . . C6 C 0.0494(2) 0.1169(5) -0.0672(4) 0.144(2) Uani 1 1 d . . . H6A H 0.0526 0.1899 -0.0548 0.172 Uiso 1 1 calc R . . H6B H 0.0049 0.0952 -0.0838 0.172 Uiso 1 1 calc R . . C8 C 0.0672(3) 0.0999(4) -0.1306(4) 0.153(3) Uani 1 1 d . . . H8A H 0.0635 0.0270 -0.1435 0.183 Uiso 1 1 calc R . . H8B H 0.0373 0.1379 -0.1753 0.183 Uiso 1 1 calc R . . C10 C 0.3248(4) 0.1538(5) -0.0469(4) 0.143(2) Uani 1 1 d . . . H10A H 0.3256 0.2240 -0.0292 0.171 Uiso 1 1 calc R . . H10B H 0.3393 0.1548 -0.0852 0.171 Uiso 1 1 calc R . . C11 C 0.2340(4) -0.0060(4) 0.2112(3) 0.130(2) Uani 1 1 d . . . H11A H 0.2337 -0.0783 0.1980 0.156 Uiso 1 1 calc R . . H11B H 0.2209 -0.0011 0.2507 0.156 Uiso 1 1 calc R . . C12 C 0.0844(3) 0.0859(4) 0.0622(4) 0.132(2) Uani 1 1 d . . . H12A H 0.0396 0.0764 0.0515 0.159 Uiso 1 1 calc R . . H12B H 0.0956 0.1581 0.0749 0.159 Uiso 1 1 calc R . . C13 C 0.1254(4) 0.0229(5) 0.1248(4) 0.141(2) Uani 1 1 d . . . H13A H 0.1182 -0.0494 0.1103 0.169 Uiso 1 1 calc R . . H13B H 0.1152 0.0335 0.1662 0.169 Uiso 1 1 calc R . . C15 C 0.2978(3) 0.0370(4) 0.2371(2) 0.134(2) Uani 1 1 d . . . H15A H 0.3275 0.0061 0.2852 0.161 Uiso 1 1 calc R . . H15B H 0.2966 0.1110 0.2445 0.161 Uiso 1 1 calc R . . C50 C 0.1500(3) 0.1267(4) -0.1677(3) 0.133(2) Uani 1 1 d . . . H50A H 0.1205 0.1654 -0.2121 0.160 Uiso 1 1 calc R . . H50B H 0.1505 0.0553 -0.1824 0.160 Uiso 1 1 calc R . . C51 C 0.2168(4) 0.1717(5) -0.1350(3) 0.150(2) Uani 1 1 d . . . H51A H 0.2295 0.1777 -0.1747 0.180 Uiso 1 1 calc R . . H51B H 0.2160 0.2408 -0.1164 0.180 Uiso 1 1 calc R . . C52 C 0.3675(3) 0.0869(5) 0.0169(5) 0.156(3) Uani 1 1 d . . . H52A H 0.3642 0.0165 -0.0014 0.187 Uiso 1 1 calc R . . H52B H 0.4121 0.1092 0.0350 0.187 Uiso 1 1 calc R . . C53 C 0.3976(3) 0.0365(5) 0.1416(5) 0.156(2) Uani 1 1 d . . . H53A H 0.4416 0.0593 0.1563 0.187 Uiso 1 1 calc R . . H53B H 0.3955 -0.0376 0.1329 0.187 Uiso 1 1 calc R . . C54 C 0.3805(3) 0.0601(5) 0.2040(4) 0.143(2) Uani 1 1 d . . . H54A H 0.4122 0.0300 0.2514 0.172 Uiso 1 1 calc R . . H54B H 0.3792 0.1343 0.2107 0.172 Uiso 1 1 calc R . . N1 N 0.22097(13) -0.01602(19) 0.52439(14) 0.0695(8) Uani 1 1 d . . . H1A H 0.1804 -0.0373 0.4954 0.104 Uiso 1 1 calc R . . H1B H 0.2349 -0.0397 0.5713 0.104 Uiso 1 1 calc R . . H1C H 0.2465 -0.0399 0.5058 0.104 Uiso 1 1 calc R . . C19 C 0.22836(18) 0.1508(3) 0.4070(2) 0.0809(11) Uani 1 1 d . . . H19 H 0.2707 0.1259 0.4293 0.097 Uiso 1 1 calc R . . C21 C 0.2228(2) 0.1013(3) 0.52562(19) 0.0935(13) Uani 1 1 d . . . H21A H 0.1998 0.1272 0.5521 0.112 Uiso 1 1 calc R . . H21B H 0.2675 0.1247 0.5526 0.112 Uiso 1 1 calc R . . C23 C 0.2032(2) 0.1942(3) 0.3370(2) 0.0784(10) Uani 1 1 d . . . H23 H 0.2287 0.1989 0.3125 0.094 Uiso 1 1 calc R . . C24 C 0.1317(2) 0.1810(3) 0.4142(2) 0.0824(11) Uani 1 1 d . . . H24 H 0.1073 0.1788 0.4402 0.099 Uiso 1 1 calc R . . C26 C 0.1159(2) 0.2811(3) 0.2256(2) 0.0836(11) Uani 1 1 d . . . C27 C 0.1049(2) 0.2246(3) 0.3413(2) 0.0872(11) Uani 1 1 d . . . H27 H 0.0625 0.2494 0.3191 0.105 Uiso 1 1 calc R . . C31 C 0.1404(2) 0.2314(3) 0.30182(19) 0.0725(10) Uani 1 1 d . . . C32 C 0.19205(19) 0.1427(3) 0.44645(18) 0.0701(9) Uani 1 1 d . . . F1 F 0.0687(7) 0.7251(15) 0.1461(6) 0.179(7) Uani 0.50 1 d P . . F1' F 0.0378(5) 0.6527(11) 0.0816(9) 0.182(5) Uani 0.50 1 d P . . F2 F 0.1484(4) 0.7240(16) 0.1251(9) 0.204(5) Uani 0.50 1 d P . . F2' F 0.1162(10) 0.7561(7) 0.1575(5) 0.164(4) Uani 0.50 1 d P . . F3 F 0.1287(7) 0.6311(10) 0.0919(8) 0.185(5) Uani 0.50 1 d P . . F3' F 0.0875(16) 0.5976(9) 0.0872(7) 0.281(13) Uani 0.50 1 d P . . F4 F 0.0798(8) 0.7690(14) 0.0407(9) 0.189(7) Uani 0.50 1 d P . . F4' F 0.0556(6) 0.7624(11) 0.0326(6) 0.120(5) Uani 0.50 1 d P . . B1 B 0.0880(3) 0.7019(5) 0.0937(3) 0.0885(14) Uani 1 1 d . . . O2 O 0.14931(16) 0.2936(2) 0.19640(14) 0.1110(10) 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 O1 0.122(2) 0.118(3) 0.0855(19) 0.0276(18) 0.0429(18) 0.004(2) O3 0.102(2) 0.088(2) 0.139(3) -0.010(2) 0.056(2) -0.0009(18) O4 0.157(3) 0.090(2) 0.108(2) 0.0101(18) 0.081(2) -0.001(2) O5 0.116(3) 0.108(2) 0.099(2) 0.0047(18) 0.021(2) 0.011(2) O6 0.144(3) 0.106(3) 0.190(4) 0.013(3) 0.118(3) 0.005(2) O8 0.138(3) 0.099(2) 0.085(2) -0.0064(17) 0.031(2) 0.014(2) O7 0.198(4) 0.077(2) 0.116(2) 0.0091(18) 0.106(3) 0.000(2) C6 0.077(3) 0.150(5) 0.174(6) 0.011(5) 0.033(4) 0.013(3) C8 0.135(5) 0.103(4) 0.129(5) 0.001(4) -0.015(4) 0.018(4) C10 0.209(7) 0.117(5) 0.168(6) -0.009(4) 0.143(5) -0.051(5) C11 0.225(7) 0.095(4) 0.096(4) 0.002(3) 0.095(4) 0.002(4) C12 0.139(4) 0.107(4) 0.215(6) -0.017(5) 0.135(5) -0.012(4) C13 0.212(7) 0.106(4) 0.178(6) 0.006(4) 0.153(6) -0.008(5) C15 0.211(6) 0.112(4) 0.065(3) 0.003(3) 0.051(4) 0.027(4) C50 0.209(6) 0.099(4) 0.091(4) 0.017(3) 0.070(4) 0.034(4) C51 0.282(9) 0.106(4) 0.104(4) 0.006(3) 0.126(5) 0.008(5) C52 0.195(6) 0.101(4) 0.249(8) -0.040(5) 0.168(7) -0.045(5) C53 0.102(4) 0.123(5) 0.197(7) 0.025(5) 0.031(5) 0.021(4) C54 0.102(4) 0.120(5) 0.156(6) 0.013(4) 0.016(4) -0.002(4) N1 0.089(2) 0.0597(17) 0.0663(17) 0.0024(13) 0.0420(15) 0.0000(15) C19 0.096(3) 0.059(2) 0.094(3) 0.004(2) 0.050(2) 0.002(2) C21 0.154(4) 0.056(2) 0.067(2) -0.0001(17) 0.049(2) -0.009(2) C23 0.106(3) 0.068(2) 0.081(2) 0.0025(19) 0.060(2) -0.001(2) C24 0.104(3) 0.088(3) 0.080(2) 0.020(2) 0.064(2) 0.007(2) C26 0.102(3) 0.074(3) 0.076(3) -0.006(2) 0.042(3) -0.006(2) C27 0.100(3) 0.074(3) 0.089(3) 0.011(2) 0.045(2) 0.011(2) C31 0.107(3) 0.062(2) 0.0603(19) -0.0002(16) 0.049(2) -0.009(2) C32 0.086(3) 0.063(2) 0.062(2) -0.0030(17) 0.036(2) -0.009(2) F1 0.172(9) 0.298(17) 0.094(6) 0.084(8) 0.084(7) 0.144(10) F1' 0.138(7) 0.160(9) 0.247(15) 0.001(9) 0.089(7) -0.039(6) F2 0.082(5) 0.307(18) 0.215(11) 0.080(11) 0.062(6) 0.016(7) F2' 0.231(13) 0.136(6) 0.092(5) -0.027(4) 0.047(8) -0.009(9) F3 0.226(11) 0.099(7) 0.285(12) -0.019(8) 0.164(10) 0.041(8) F3' 0.57(4) 0.099(8) 0.133(7) -0.021(5) 0.130(14) -0.122(14) F4 0.223(17) 0.204(12) 0.148(10) 0.066(8) 0.094(11) -0.027(10) F4' 0.109(6) 0.180(11) 0.072(4) 0.027(5) 0.041(4) 0.074(7) B1 0.066(3) 0.112(5) 0.083(3) 0.009(3) 0.031(3) 0.004(3) O2 0.153(3) 0.122(3) 0.0868(19) 0.0108(17) 0.080(2) 0.007(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C26 1.305(5) . ? O1 H1D 0.8500 . ? O3 C6 1.396(6) . ? O3 C12 1.419(6) . ? O4 C11 1.374(6) . ? O4 C13 1.441(6) . ? O5 C54 1.368(6) . ? O5 C15 1.440(6) . ? O6 C52 1.327(6) . ? O6 C53 1.413(7) . ? O8 C8 1.363(6) . ? O8 C50 1.473(5) . ? O7 C51 1.367(6) . ? O7 C10 1.392(5) . ? C6 C8 1.518(8) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C10 C52 1.475(8) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C15 1.437(7) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.422(7) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C50 C51 1.494(7) . ? C50 H50A 0.9700 . ? C50 H50B 0.9700 . ? C51 H51A 0.9700 . ? C51 H51B 0.9700 . ? C52 H52A 0.9700 . ? C52 H52B 0.9700 . ? C53 C54 1.505(8) . ? C53 H53A 0.9700 . ? C53 H53B 0.9700 . ? C54 H54A 0.9700 . ? C54 H54B 0.9700 . ? N1 C21 1.517(4) . ? N1 H1A 0.8900 . ? N1 H1B 0.8900 . ? N1 H1C 0.8900 . ? C19 C23 1.358(5) . ? C19 C32 1.401(5) . ? C19 H19 0.9300 . ? C21 C32 1.497(4) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C23 C31 1.380(5) . ? C23 H23 0.9300 . ? C24 C32 1.337(4) . ? C24 C27 1.407(5) . ? C24 H24 0.9300 . ? C26 O2 1.180(4) . ? C26 C31 1.497(5) . ? C27 C31 1.384(5) . ? C27 H27 0.9300 . ? F1 F2' 1.094(12) . ? F1 B1 1.350(10) . ? F1 F1' 1.479(15) . ? F1' B1 1.252(11) . ? F1' F3' 1.32(3) . ? F2 F2' 1.265(12) . ? F2 B1 1.276(10) . ? F2 F3 1.346(16) . ? F2' B1 1.328(10) . ? F3 F3' 1.02(2) . ? F3 B1 1.330(10) . ? F3' B1 1.353(13) . ? F4 F4' 0.52(3) . ? F4 B1 1.311(16) . ? F4' B1 1.345(14) . ? 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 C26 O1 H1D 108.2 . . ? C6 O3 C12 113.3(5) . . ? C11 O4 C13 111.9(5) . . ? C54 O5 C15 111.7(5) . . ? C52 O6 C53 117.4(6) . . ? C8 O8 C50 114.7(5) . . ? C51 O7 C10 113.9(5) . . ? O3 C6 C8 110.3(5) . . ? O3 C6 H6A 109.6 . . ? C8 C6 H6A 109.6 . . ? O3 C6 H6B 109.6 . . ? C8 C6 H6B 109.6 . . ? H6A C6 H6B 108.1 . . ? O8 C8 C6 110.0(5) . . ? O8 C8 H8A 109.7 . . ? C6 C8 H8A 109.7 . . ? O8 C8 H8B 109.7 . . ? C6 C8 H8B 109.7 . . ? H8A C8 H8B 108.2 . . ? O7 C10 C52 107.9(5) . . ? O7 C10 H10A 110.1 . . ? C52 C10 H10A 110.1 . . ? O7 C10 H10B 110.1 . . ? C52 C10 H10B 110.1 . . ? H10A C10 H10B 108.4 . . ? O4 C11 C15 107.4(5) . . ? O4 C11 H11A 110.2 . . ? C15 C11 H11A 110.2 . . ? O4 C11 H11B 110.2 . . ? C15 C11 H11B 110.2 . . ? H11A C11 H11B 108.5 . . ? O3 C12 C13 111.1(4) . . ? O3 C12 H12A 109.4 . . ? C13 C12 H12A 109.4 . . ? O3 C12 H12B 109.4 . . ? C13 C12 H12B 109.4 . . ? H12A C12 H12B 108.0 . . ? C12 C13 O4 109.4(5) . . ? C12 C13 H13A 109.8 . . ? O4 C13 H13A 109.8 . . ? C12 C13 H13B 109.8 . . ? O4 C13 H13B 109.8 . . ? H13A C13 H13B 108.2 . . ? C11 C15 O5 110.1(4) . . ? C11 C15 H15A 109.6 . . ? O5 C15 H15A 109.6 . . ? C11 C15 H15B 109.6 . . ? O5 C15 H15B 109.6 . . ? H15A C15 H15B 108.2 . . ? O8 C50 C51 107.1(4) . . ? O8 C50 H50A 110.3 . . ? C51 C50 H50A 110.3 . . ? O8 C50 H50B 110.3 . . ? C51 C50 H50B 110.3 . . ? H50A C50 H50B 108.5 . . ? O7 C51 C50 113.1(5) . . ? O7 C51 H51A 109.0 . . ? C50 C51 H51A 109.0 . . ? O7 C51 H51B 109.0 . . ? C50 C51 H51B 109.0 . . ? H51A C51 H51B 107.8 . . ? O6 C52 C10 113.9(5) . . ? O6 C52 H52A 108.8 . . ? C10 C52 H52A 108.8 . . ? O6 C52 H52B 108.8 . . ? C10 C52 H52B 108.8 . . ? H52A C52 H52B 107.7 . . ? O6 C53 C54 109.7(5) . . ? O6 C53 H53A 109.7 . . ? C54 C53 H53A 109.7 . . ? O6 C53 H53B 109.7 . . ? C54 C53 H53B 109.7 . . ? H53A C53 H53B 108.2 . . ? O5 C54 C53 106.3(5) . . ? O5 C54 H54A 110.5 . . ? C53 C54 H54A 110.5 . . ? O5 C54 H54B 110.5 . . ? C53 C54 H54B 110.5 . . ? H54A C54 H54B 108.7 . . ? C21 N1 H1A 109.5 . . ? C21 N1 H1B 109.5 . . ? H1A N1 H1B 109.5 . . ? C21 N1 H1C 109.5 . . ? H1A N1 H1C 109.5 . . ? H1B N1 H1C 109.5 . . ? C23 C19 C32 121.6(4) . . ? C23 C19 H19 119.2 . . ? C32 C19 H19 119.2 . . ? C32 C21 N1 110.2(3) . . ? C32 C21 H21A 109.6 . . ? N1 C21 H21A 109.6 . . ? C32 C21 H21B 109.6 . . ? N1 C21 H21B 109.6 . . ? H21A C21 H21B 108.1 . . ? C19 C23 C31 120.9(4) . . ? C19 C23 H23 119.5 . . ? C31 C23 H23 119.5 . . ? C32 C24 C27 120.4(3) . . ? C32 C24 H24 119.8 . . ? C27 C24 H24 119.8 . . ? O2 C26 O1 126.3(4) . . ? O2 C26 C31 122.2(4) . . ? O1 C26 C31 111.4(4) . . ? C31 C27 C24 121.3(4) . . ? C31 C27 H27 119.4 . . ? C24 C27 H27 119.4 . . ? C23 C31 C27 117.4(3) . . ? C23 C31 C26 118.6(4) . . ? C27 C31 C26 123.9(4) . . ? C24 C32 C19 118.4(3) . . ? C24 C32 C21 121.2(3) . . ? C19 C32 C21 120.1(4) . . ? F2' F1 B1 64.8(7) . . ? F2' F1 F1' 116.6(11) . . ? B1 F1 F1' 52.3(6) . . ? B1 F1' F3' 63.4(8) . . ? B1 F1' F1 58.6(6) . . ? F3' F1' F1 102.4(12) . . ? F2' F2 B1 63.1(6) . . ? F2' F2 F3 113.4(11) . . ? B1 F2 F3 60.9(8) . . ? F1 F2' F2 123.7(13) . . ? F1 F2' B1 66.9(8) . . ? F2 F2' B1 58.9(7) . . ? F3' F3 B1 69.0(13) . . ? F3' F3 F2 121.0(15) . . ? B1 F3 F2 56.9(5) . . ? F3 F3' F1' 122.2(14) . . ? F3 F3' B1 66.5(8) . . ? F1' F3' B1 55.9(8) . . ? F4' F4 B1 83(3) . . ? F4 F4' B1 75(3) . . ? F1' B1 F2 157.6(9) . . ? F1' B1 F4 114.1(10) . . ? F2 B1 F4 87.8(10) . . ? F1' B1 F3 105.0(9) . . ? F2 B1 F3 62.2(8) . . ? F4 B1 F3 105.8(10) . . ? F1' B1 F2' 116.8(10) . . ? F2 B1 F2' 58.1(7) . . ? F4 B1 F2' 104.2(11) . . ? F3 B1 F2' 110.4(9) . . ? F1' B1 F4' 92.3(10) . . ? F2 B1 F4' 109.9(9) . . ? F4 B1 F4' 22.4(11) . . ? F3 B1 F4' 118.9(8) . . ? F2' B1 F4' 112.3(9) . . ? F1' B1 F1 69.1(8) . . ? F2 B1 F1 104.8(9) . . ? F4 B1 F1 120.1(11) . . ? F3 B1 F1 132.2(8) . . ? F2' B1 F1 48.2(6) . . ? F4' B1 F1 108.8(7) . . ? F1' B1 F3' 60.7(11) . . ? F2 B1 F3' 103.3(13) . . ? F4 B1 F3' 126.2(11) . . ? F3 B1 F3' 44.5(11) . . ? F2' B1 F3' 126.5(8) . . ? F4' B1 F3' 121.1(10) . . ? F1 B1 F3' 107.7(10) . . ? 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 C12 O3 C6 C8 170.0(5) . . . . ? C50 O8 C8 C6 -175.9(4) . . . . ? O3 C6 C8 O8 -60.8(6) . . . . ? C51 O7 C10 C52 177.3(5) . . . . ? C13 O4 C11 C15 -171.5(4) . . . . ? C6 O3 C12 C13 177.1(5) . . . . ? O3 C12 C13 O4 68.6(6) . . . . ? C11 O4 C13 C12 177.5(4) . . . . ? O4 C11 C15 O5 -67.3(5) . . . . ? C54 O5 C15 C11 178.2(5) . . . . ? C8 O8 C50 C51 176.4(4) . . . . ? C10 O7 C51 C50 178.9(5) . . . . ? O8 C50 C51 O7 66.6(5) . . . . ? C53 O6 C52 C10 -171.9(5) . . . . ? O7 C10 C52 O6 -64.7(6) . . . . ? C52 O6 C53 C54 170.7(5) . . . . ? C15 O5 C54 C53 -178.7(4) . . . . ? O6 C53 C54 O5 64.8(6) . . . . ? C32 C19 C23 C31 -0.5(5) . . . . ? C32 C24 C27 C31 -1.5(6) . . . . ? C19 C23 C31 C27 1.4(5) . . . . ? C19 C23 C31 C26 178.3(3) . . . . ? C24 C27 C31 C23 -0.4(5) . . . . ? C24 C27 C31 C26 -177.1(4) . . . . ? O2 C26 C31 C23 -3.5(6) . . . . ? O1 C26 C31 C23 178.9(3) . . . . ? O2 C26 C31 C27 173.2(4) . . . . ? O1 C26 C31 C27 -4.4(5) . . . . ? C27 C24 C32 C19 2.4(5) . . . . ? C27 C24 C32 C21 176.6(3) . . . . ? C23 C19 C32 C24 -1.4(5) . . . . ? C23 C19 C32 C21 -175.7(3) . . . . ? N1 C21 C32 C24 102.1(4) . . . . ? N1 C21 C32 C19 -83.8(4) . . . . ? F2' F1 F1' B1 -8.8(13) . . . . ? F2' F1 F1' F3' 39.0(18) . . . . ? B1 F1 F1' F3' 47.8(9) . . . . ? B1 F1 F2' F2 -16.5(12) . . . . ? F1' F1 F2' F2 -9(2) . . . . ? F1' F1 F2' B1 7.7(11) . . . . ? B1 F2 F2' F1 17.8(13) . . . . ? F3 F2 F2' F1 -17.6(19) . . . . ? F3 F2 F2' B1 -35.4(10) . . . . ? F2' F2 F3 F3' 9(2) . . . . ? B1 F2 F3 F3' -27.2(17) . . . . ? F2' F2 F3 B1 36.2(9) . . . . ? B1 F3 F3' F1' 5.4(16) . . . . ? F2 F3 F3' F1' 30(3) . . . . ? F2 F3 F3' B1 24.2(14) . . . . ? B1 F1' F3' F3 -6.0(18) . . . . ? F1 F1' F3' F3 -51(2) . . . . ? F1 F1' F3' B1 -45.0(8) . . . . ? F3' F1' B1 F2 -48(3) . . . . ? F1 F1' B1 F2 78(3) . . . . ? F3' F1' B1 F4 119.4(12) . . . . ? F1 F1' B1 F4 -114.6(12) . . . . ? F3' F1' B1 F3 4.0(12) . . . . ? F1 F1' B1 F3 130.0(8) . . . . ? F3' F1' B1 F2' -118.7(10) . . . . ? F1 F1' B1 F2' 7.2(10) . . . . ? F3' F1' B1 F4' 124.7(10) . . . . ? F1 F1' B1 F4' -109.3(8) . . . . ? F3' F1' B1 F1 -126.0(11) . . . . ? F1 F1' B1 F3' 126.0(11) . . . . ? F2' F2 B1 F1' -83(3) . . . . ? F3 F2 B1 F1' 59(3) . . . . ? F2' F2 B1 F4 108.3(10) . . . . ? F3 F2 B1 F4 -109.2(11) . . . . ? F2' F2 B1 F3 -142.6(10) . . . . ? F3 F2 B1 F2' 142.6(10) . . . . ? F2' F2 B1 F4' 104.5(9) . . . . ? F3 F2 B1 F4' -112.9(9) . . . . ? F2' F2 B1 F1 -12.3(10) . . . . ? F3 F2 B1 F1 130.3(9) . . . . ? F2' F2 B1 F3' -125.0(9) . . . . ? F3 F2 B1 F3' 17.6(10) . . . . ? F4' F4 B1 F1' 14(4) . . . . ? F4' F4 B1 F2 -171(3) . . . . ? F4' F4 B1 F3 129(3) . . . . ? F4' F4 B1 F2' -114(3) . . . . ? F4' F4 B1 F1 -65(4) . . . . ? F4' F4 B1 F3' 84(4) . . . . ? F3' F3 B1 F1' -5.0(15) . . . . ? F2 F3 B1 F1' -160.2(10) . . . . ? F3' F3 B1 F2 155.2(15) . . . . ? F3' F3 B1 F4 -126.0(14) . . . . ? F2 F3 B1 F4 78.8(12) . . . . ? F3' F3 B1 F2' 121.8(13) . . . . ? F2 F3 B1 F2' -33.4(9) . . . . ? F3' F3 B1 F4' -106.3(15) . . . . ? F2 F3 B1 F4' 98.5(12) . . . . ? F3' F3 B1 F1 70.3(19) . . . . ? F2 F3 B1 F1 -84.9(14) . . . . ? F2 F3 B1 F3' -155.2(15) . . . . ? F1 F2' B1 F1' -9.1(13) . . . . ? F2 F2' B1 F1' 154.9(11) . . . . ? F1 F2' B1 F2 -164.0(12) . . . . ? F1 F2' B1 F4 117.8(12) . . . . ? F2 F2' B1 F4 -78.2(10) . . . . ? F1 F2' B1 F3 -129.0(11) . . . . ? F2 F2' B1 F3 35.0(9) . . . . ? F1 F2' B1 F4' 95.8(11) . . . . ? F2 F2' B1 F4' -100.2(10) . . . . ? F2 F2' B1 F1 164.0(12) . . . . ? F1 F2' B1 F3' -81.1(17) . . . . ? F2 F2' B1 F3' 82.8(17) . . . . ? F4 F4' B1 F1' -167(3) . . . . ? F4 F4' B1 F2 10(3) . . . . ? F4 F4' B1 F3 -59(4) . . . . ? F4 F4' B1 F2' 73(3) . . . . ? F4 F4' B1 F1 124(3) . . . . ? F4 F4' B1 F3' -110(4) . . . . ? F2' F1 B1 F1' 171.3(12) . . . . ? F2' F1 B1 F2 14.0(11) . . . . ? F1' F1 B1 F2 -157.3(10) . . . . ? F2' F1 B1 F4 -82.2(13) . . . . ? F1' F1 B1 F4 106.5(13) . . . . ? F2' F1 B1 F3 79.7(17) . . . . ? F1' F1 B1 F3 -91.6(13) . . . . ? F1' F1 B1 F2' -171.3(12) . . . . ? F2' F1 B1 F4' -103.5(12) . . . . ? F1' F1 B1 F4' 85.2(11) . . . . ? F2' F1 B1 F3' 123.5(13) . . . . ? F1' F1 B1 F3' -47.8(12) . . . . ? F3 F3' B1 F1' 174.5(17) . . . . ? F3 F3' B1 F2 -22.4(14) . . . . ? F1' F3' B1 F2 163.1(11) . . . . ? F3 F3' B1 F4 74.7(19) . . . . ? F1' F3' B1 F4 -99.8(15) . . . . ? F1' F3' B1 F3 -174.5(17) . . . . ? F3 F3' B1 F2' -82.3(16) . . . . ? F1' F3' B1 F2' 103.2(15) . . . . ? F3 F3' B1 F4' 101.0(16) . . . . ? F1' F3' B1 F4' -73.5(13) . . . . ? F3 F3' B1 F1 -133.0(12) . . . . ? F1' F3' B1 F1 52.5(10) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.43 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.498 _refine_diff_density_min -0.158 _refine_diff_density_rms 0.043 _database_code_depnum_ccdc_archive 'CCDC 946956' ####################################################################### # # 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_lyh _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H24 O6, C7 H8 N O2, B F4' _chemical_formula_sum 'C19 H32 B F4 N O8' _chemical_formula_weight 489.27 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' F F 0.0171 0.0103 '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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.3105(19) _cell_length_b 10.982(2) _cell_length_c 11.809(2) _cell_angle_alpha 82.80(3) _cell_angle_beta 89.03(3) _cell_angle_gamma 85.61(3) _cell_volume 1194.4(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1621 _cell_measurement_theta_min 2.99 _cell_measurement_theta_max 27.49 _exptl_crystal_description Cubic _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.360 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 516 _exptl_absorpt_coefficient_mu 0.122 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.964 _exptl_absorpt_correction_T_max 0.982 _exptl_absorpt_process_details 'CrystalClear (Rigaku, 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku SCXmini diffractometer' _diffrn_measurement_method CCD_Profile_fitting _diffrn_detector_area_resol_mean 13.6612 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12097 _diffrn_reflns_av_R_equivalents 0.1364 _diffrn_reflns_av_sigmaI/netI 0.2027 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 27.49 _reflns_number_total 5434 _reflns_number_gt 1621 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku, 2005)' _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _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^)+(0.1704P)^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 5434 _refine_ls_number_parameters 300 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2934 _refine_ls_R_factor_gt 0.1125 _refine_ls_wR_factor_ref 0.3904 _refine_ls_wR_factor_gt 0.2889 _refine_ls_goodness_of_fit_ref 0.942 _refine_ls_restrained_S_all 0.942 _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 0.9708(13) 0.2657(10) 0.2616(11) 0.095(3) Uani 1 1 d . . . C1 C 0.1898(6) 0.5108(5) 0.4315(5) 0.0526(15) Uani 1 1 d . . . F1 F 1.1113(6) 0.2870(6) 0.2821(5) 0.155(2) Uani 1 1 d . . . N1 N 0.5679(5) 0.7505(4) 0.2276(4) 0.0542(13) Uani 1 1 d . . . H2A H 0.5994 0.7951 0.2787 0.081 Uiso 1 1 calc R . . H2B H 0.4946 0.7924 0.1893 0.081 Uiso 1 1 calc R . . H2C H 0.6389 0.7342 0.1790 0.081 Uiso 1 1 calc R . . O1 O 0.1594(4) 0.4247(4) 0.5026(4) 0.0658(12) Uani 1 1 d . . . C2 C 0.3353(6) 0.5182(5) 0.3827(5) 0.0469(14) Uani 1 1 d . . . F2 F 0.9742(6) 0.1827(6) 0.1884(5) 0.149(2) Uani 1 1 d . . . O2 O 0.0972(5) 0.6032(4) 0.3961(4) 0.0810(15) Uani 1 1 d . . . H2 H 0.0250 0.6005 0.4367 0.121 Uiso 1 1 calc R . . C3 C 0.3801(6) 0.6292(5) 0.3249(5) 0.0502(15) Uani 1 1 d . . . H3 H 0.3157 0.6985 0.3128 0.060 Uiso 1 1 calc R . . F3 F 0.9174(9) 0.2197(8) 0.3644(6) 0.212(4) Uani 1 1 d . . . O3 O 0.3474(5) 0.0873(4) 0.6077(4) 0.0719(14) Uani 1 1 d . . . C4 C 0.5196(6) 0.6338(5) 0.2867(5) 0.0475(15) Uani 1 1 d . . . F4 F 0.9087(9) 0.3699(7) 0.2220(9) 0.239(4) Uani 1 1 d . . . O4 O 0.1297(5) 0.2062(4) 0.7364(4) 0.0698(13) Uani 1 1 d . . . C5 C 0.6153(7) 0.5307(5) 0.2995(5) 0.0556(16) Uani 1 1 d . . . H6 H 0.7089 0.5351 0.2715 0.067 Uiso 1 1 calc R . . O5 O 0.2090(5) 0.2925(4) 0.9384(4) 0.0734(14) Uani 1 1 d . . . C6 C 0.5712(7) 0.4208(5) 0.3542(5) 0.0569(16) Uani 1 1 d . . . H16 H 0.6349 0.3508 0.3630 0.068 Uiso 1 1 calc R . . O6 O 0.4902(8) 0.3422(5) 0.9810(5) 0.1060(19) Uani 1 1 d . . . C7 C 0.4329(7) 0.4159(5) 0.3955(5) 0.0557(16) Uani 1 1 d . . . H1 H 0.4041 0.3421 0.4330 0.067 Uiso 1 1 calc R . . O7 O 0.6756(5) 0.1431(5) 0.9121(4) 0.0856(15) Uani 1 1 d . . . C8 C 0.5328(11) -0.0609(7) 0.6704(7) 0.102(3) Uani 1 1 d . . . H8A H 0.5611 -0.1484 0.6810 0.123 Uiso 1 1 calc R . . H8B H 0.5893 -0.0229 0.6078 0.123 Uiso 1 1 calc R . . O8 O 0.5608(5) -0.0096(4) 0.7711(4) 0.0763(14) Uani 1 1 d . . . C9 C 0.3800(11) -0.0415(6) 0.6422(6) 0.090(3) Uani 1 1 d . . . H9A H 0.3588 -0.0882 0.5809 0.109 Uiso 1 1 calc R . . H9B H 0.3221 -0.0688 0.7082 0.109 Uiso 1 1 calc R . . C10 C 0.1979(9) 0.1165(7) 0.5689(6) 0.085(2) Uani 1 1 d . . . H10A H 0.1727 0.0564 0.5204 0.102 Uiso 1 1 calc R . . H10B H 0.1903 0.1968 0.5238 0.102 Uiso 1 1 calc R . . C11 C 0.0953(8) 0.1166(6) 0.6654(7) 0.088(2) Uani 1 1 d . . . H11A H -0.0020 0.1355 0.6368 0.106 Uiso 1 1 calc R . . H11B H 0.0999 0.0357 0.7095 0.106 Uiso 1 1 calc R . . C12 C 0.0367(7) 0.2110(7) 0.8302(6) 0.078(2) Uani 1 1 d . . . H12A H 0.0494 0.1344 0.8809 0.094 Uiso 1 1 calc R . . H12B H -0.0623 0.2208 0.8043 0.094 Uiso 1 1 calc R . . C13 C 0.0658(7) 0.3140(7) 0.8921(6) 0.078(2) Uani 1 1 d . . . H13A H 0.0582 0.3904 0.8408 0.093 Uiso 1 1 calc R . . H13B H -0.0040 0.3208 0.9533 0.093 Uiso 1 1 calc R . . C14 C 0.2403(10) 0.3823(7) 1.0103(7) 0.096(3) Uani 1 1 d . . . H14A H 0.1666 0.3866 1.0690 0.115 Uiso 1 1 calc R . . H14B H 0.2408 0.4626 0.9655 0.115 Uiso 1 1 calc R . . C15 C 0.3858(12) 0.3474(8) 1.0649(7) 0.102(3) Uani 1 1 d . . . H15A H 0.4072 0.4078 1.1142 0.122 Uiso 1 1 calc R . . H15B H 0.3845 0.2679 1.1110 0.122 Uiso 1 1 calc R . . C16 C 0.6390(12) 0.3059(10) 1.0186(9) 0.132(4) Uani 1 1 d . . . H16A H 0.7041 0.3511 0.9673 0.158 Uiso 1 1 calc R . . H16B H 0.6505 0.3301 1.0940 0.158 Uiso 1 1 calc R . . C17 C 0.6814(11) 0.1749(11) 1.0231(8) 0.126(4) Uani 1 1 d . . . H17A H 0.7783 0.1574 1.0527 0.152 Uiso 1 1 calc R . . H17B H 0.6166 0.1276 1.0730 0.152 Uiso 1 1 calc R . . C18 C 0.7242(9) 0.0130(8) 0.9124(10) 0.114(4) Uani 1 1 d . . . H18A H 0.8243 -0.0003 0.9352 0.137 Uiso 1 1 calc R . . H18B H 0.6675 -0.0372 0.9669 0.137 Uiso 1 1 calc R . . C19 C 0.7087(9) -0.0215(7) 0.8011(10) 0.105(3) Uani 1 1 d . . . H19A H 0.7626 0.0308 0.7463 0.126 Uiso 1 1 calc R . . H19B H 0.7470 -0.1060 0.7998 0.126 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 0.105(9) 0.074(6) 0.106(9) -0.019(6) 0.027(7) -0.001(6) C1 0.041(4) 0.053(4) 0.062(4) 0.004(3) 0.005(3) -0.008(3) F1 0.095(4) 0.239(7) 0.148(5) -0.070(5) -0.004(4) -0.043(4) N1 0.054(3) 0.051(3) 0.058(3) -0.004(2) 0.006(2) -0.016(2) O1 0.055(3) 0.068(3) 0.071(3) 0.010(2) 0.007(2) -0.013(2) C2 0.042(3) 0.048(3) 0.051(4) -0.004(3) 0.005(3) -0.013(3) F2 0.144(5) 0.140(5) 0.173(6) -0.045(5) -0.032(4) -0.018(4) O2 0.049(3) 0.080(3) 0.104(4) 0.022(3) 0.015(3) 0.002(3) C3 0.041(4) 0.039(3) 0.071(4) -0.006(3) 0.000(3) -0.007(3) F3 0.230(9) 0.262(9) 0.148(6) -0.002(6) 0.034(6) -0.100(7) O3 0.091(4) 0.052(3) 0.075(3) -0.012(2) 0.007(3) -0.015(2) C4 0.048(4) 0.048(3) 0.046(4) 0.002(3) -0.003(3) -0.017(3) F4 0.204(8) 0.131(6) 0.352(11) 0.039(7) 0.025(7) 0.067(5) O4 0.056(3) 0.068(3) 0.087(3) -0.009(2) -0.002(3) -0.010(2) C5 0.047(4) 0.060(4) 0.060(4) -0.007(3) -0.002(3) -0.006(3) O5 0.073(3) 0.073(3) 0.076(3) -0.015(2) 0.012(3) -0.011(2) C6 0.055(4) 0.045(3) 0.068(4) 0.002(3) 0.008(3) -0.004(3) O6 0.123(5) 0.103(4) 0.100(5) -0.034(3) -0.018(4) -0.018(4) C7 0.061(4) 0.046(3) 0.060(4) -0.006(3) 0.003(3) -0.006(3) O7 0.071(3) 0.107(4) 0.078(4) -0.003(3) -0.018(3) -0.013(3) C8 0.157(9) 0.072(5) 0.071(6) -0.013(4) 0.007(6) 0.037(5) O8 0.059(3) 0.072(3) 0.095(4) -0.004(3) 0.002(3) 0.008(2) C9 0.151(8) 0.058(5) 0.066(5) -0.012(4) -0.023(5) -0.018(5) C10 0.097(6) 0.100(6) 0.061(5) -0.012(4) 0.001(5) -0.035(5) C11 0.086(6) 0.073(5) 0.110(7) -0.012(5) -0.016(5) -0.033(4) C12 0.054(4) 0.087(5) 0.089(6) 0.001(4) 0.008(4) -0.006(4) C13 0.057(5) 0.087(5) 0.085(5) -0.004(4) 0.010(4) 0.003(4) C14 0.130(8) 0.079(5) 0.087(6) -0.039(5) 0.031(6) -0.020(5) C15 0.144(9) 0.103(6) 0.064(6) -0.010(5) -0.007(6) -0.048(6) C16 0.155(10) 0.118(8) 0.131(9) -0.025(6) -0.091(8) -0.022(7) C17 0.108(8) 0.167(11) 0.103(8) 0.002(7) -0.047(6) -0.024(7) C18 0.070(6) 0.089(7) 0.169(11) 0.047(7) -0.020(7) -0.004(5) C19 0.067(6) 0.069(5) 0.174(10) 0.003(6) 0.018(6) 0.006(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 F4 1.279(11) . ? B1 F2 1.330(11) . ? B1 F3 1.357(12) . ? B1 F1 1.377(12) . ? C1 O1 1.230(6) . ? C1 O2 1.312(7) . ? C1 C2 1.466(8) . ? N1 C4 1.478(6) . ? N1 H2A 0.8900 . ? N1 H2B 0.8900 . ? N1 H2C 0.8900 . ? C2 C7 1.384(8) . ? C2 C3 1.410(7) . ? O2 H2 0.8200 . ? C3 C4 1.370(7) . ? C3 H3 0.9300 . ? O3 C9 1.432(8) . ? O3 C10 1.473(8) . ? C4 C5 1.380(8) . ? O4 C12 1.398(7) . ? O4 C11 1.428(8) . ? C5 C6 1.384(8) . ? C5 H6 0.9300 . ? O5 C14 1.428(8) . ? O5 C13 1.440(8) . ? C6 C7 1.371(8) . ? C6 H16 0.9300 . ? O6 C15 1.379(10) . ? O6 C16 1.473(10) . ? C7 H1 0.9300 . ? O7 C17 1.402(10) . ? O7 C18 1.464(10) . ? C8 O8 1.414(9) . ? C8 C9 1.460(11) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? O8 C19 1.421(9) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.474(10) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.467(9) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.512(11) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.456(12) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.425(11) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? 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 F4 B1 F2 113.4(11) . . ? F4 B1 F3 113.2(10) . . ? F2 B1 F3 111.0(9) . . ? F4 B1 F1 106.2(9) . . ? F2 B1 F1 107.3(8) . . ? F3 B1 F1 105.1(10) . . ? O1 C1 O2 123.1(5) . . ? O1 C1 C2 121.6(5) . . ? O2 C1 C2 115.3(5) . . ? C4 N1 H2A 109.5 . . ? C4 N1 H2B 109.5 . . ? H2A N1 H2B 109.5 . . ? C4 N1 H2C 109.5 . . ? H2A N1 H2C 109.5 . . ? H2B N1 H2C 109.5 . . ? C7 C2 C3 118.6(5) . . ? C7 C2 C1 120.2(5) . . ? C3 C2 C1 121.2(5) . . ? C1 O2 H2 109.5 . . ? C4 C3 C2 119.2(5) . . ? C4 C3 H3 120.4 . . ? C2 C3 H3 120.4 . . ? C9 O3 C10 112.9(6) . . ? C3 C4 C5 121.3(5) . . ? C3 C4 N1 119.5(5) . . ? C5 C4 N1 119.1(5) . . ? C12 O4 C11 112.8(6) . . ? C4 C5 C6 119.7(6) . . ? C4 C5 H6 120.1 . . ? C6 C5 H6 120.1 . . ? C14 O5 C13 112.3(6) . . ? C7 C6 C5 119.4(6) . . ? C7 C6 H16 120.3 . . ? C5 C6 H16 120.3 . . ? C15 O6 C16 117.0(8) . . ? C6 C7 C2 121.7(6) . . ? C6 C7 H1 119.2 . . ? C2 C7 H1 119.2 . . ? C17 O7 C18 109.6(8) . . ? O8 C8 C9 110.5(7) . . ? O8 C8 H8A 109.5 . . ? C9 C8 H8A 109.5 . . ? O8 C8 H8B 109.5 . . ? C9 C8 H8B 109.5 . . ? H8A C8 H8B 108.1 . . ? C8 O8 C19 113.4(7) . . ? O3 C9 C8 108.1(6) . . ? O3 C9 H9A 110.1 . . ? C8 C9 H9A 110.1 . . ? O3 C9 H9B 110.1 . . ? C8 C9 H9B 110.1 . . ? H9A C9 H9B 108.4 . . ? O3 C10 C11 112.0(6) . . ? O3 C10 H10A 109.2 . . ? C11 C10 H10A 109.2 . . ? O3 C10 H10B 109.2 . . ? C11 C10 H10B 109.2 . . ? H10A C10 H10B 107.9 . . ? O4 C11 C10 109.8(6) . . ? O4 C11 H11A 109.7 . . ? C10 C11 H11A 109.7 . . ? O4 C11 H11B 109.7 . . ? C10 C11 H11B 109.7 . . ? H11A C11 H11B 108.2 . . ? O4 C12 C13 110.5(6) . . ? O4 C12 H12A 109.6 . . ? C13 C12 H12A 109.6 . . ? O4 C12 H12B 109.6 . . ? C13 C12 H12B 109.6 . . ? H12A C12 H12B 108.1 . . ? O5 C13 C12 108.8(6) . . ? O5 C13 H13A 109.9 . . ? C12 C13 H13A 109.9 . . ? O5 C13 H13B 109.9 . . ? C12 C13 H13B 109.9 . . ? H13A C13 H13B 108.3 . . ? O5 C14 C15 109.5(6) . . ? O5 C14 H14A 109.8 . . ? C15 C14 H14A 109.8 . . ? O5 C14 H14B 109.8 . . ? C15 C14 H14B 109.8 . . ? H14A C14 H14B 108.2 . . ? O6 C15 C14 109.5(7) . . ? O6 C15 H15A 109.8 . . ? C14 C15 H15A 109.8 . . ? O6 C15 H15B 109.8 . . ? C14 C15 H15B 109.8 . . ? H15A C15 H15B 108.2 . . ? C17 C16 O6 114.9(8) . . ? C17 C16 H16A 108.5 . . ? O6 C16 H16A 108.5 . . ? C17 C16 H16B 108.5 . . ? O6 C16 H16B 108.5 . . ? H16A C16 H16B 107.5 . . ? O7 C17 C16 108.1(8) . . ? O7 C17 H17A 110.1 . . ? C16 C17 H17A 110.1 . . ? O7 C17 H17B 110.1 . . ? C16 C17 H17B 110.1 . . ? H17A C17 H17B 108.4 . . ? C19 C18 O7 109.6(7) . . ? C19 C18 H18A 109.8 . . ? O7 C18 H18A 109.8 . . ? C19 C18 H18B 109.8 . . ? O7 C18 H18B 109.8 . . ? H18A C18 H18B 108.2 . . ? O8 C19 C18 109.7(8) . . ? O8 C19 H19A 109.7 . . ? C18 C19 H19A 109.7 . . ? O8 C19 H19B 109.7 . . ? C18 C19 H19B 109.7 . . ? H19A C19 H19B 108.2 . . ? 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 C1 C2 C7 14.6(9) . . . . ? O2 C1 C2 C7 -166.9(6) . . . . ? O1 C1 C2 C3 -163.6(6) . . . . ? O2 C1 C2 C3 14.8(8) . . . . ? C7 C2 C3 C4 -2.2(8) . . . . ? C1 C2 C3 C4 176.1(5) . . . . ? C2 C3 C4 C5 2.8(9) . . . . ? C2 C3 C4 N1 -179.1(5) . . . . ? C3 C4 C5 C6 -1.5(9) . . . . ? N1 C4 C5 C6 -179.7(5) . . . . ? C4 C5 C6 C7 -0.2(9) . . . . ? C5 C6 C7 C2 0.7(9) . . . . ? C3 C2 C7 C6 0.5(9) . . . . ? C1 C2 C7 C6 -177.8(6) . . . . ? C9 C8 O8 C19 -177.9(6) . . . . ? C10 O3 C9 C8 175.7(6) . . . . ? O8 C8 C9 O3 69.1(8) . . . . ? C9 O3 C10 C11 77.8(7) . . . . ? C12 O4 C11 C10 -179.8(6) . . . . ? O3 C10 C11 O4 59.8(8) . . . . ? C11 O4 C12 C13 -173.2(6) . . . . ? C14 O5 C13 C12 -173.8(6) . . . . ? O4 C12 C13 O5 -64.2(7) . . . . ? C13 O5 C14 C15 174.5(6) . . . . ? C16 O6 C15 C14 -178.3(6) . . . . ? O5 C14 C15 O6 59.9(9) . . . . ? C15 O6 C16 C17 93.3(10) . . . . ? C18 O7 C17 C16 177.3(8) . . . . ? O6 C16 C17 O7 63.0(12) . . . . ? C17 O7 C18 C19 176.0(7) . . . . ? C8 O8 C19 C18 -170.2(7) . . . . ? O7 C18 C19 O8 -63.3(9) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.553 _refine_diff_density_min -0.266 _refine_diff_density_rms 0.070 _database_code_depnum_ccdc_archive 'CCDC 946959'