# 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 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H41 Br N2 O2' _chemical_formula_weight 445.48 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' Br Br -0.2901 2.4595 '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 22.834(7) _cell_length_b 8.194(3) _cell_length_c 13.429(4) _cell_angle_alpha 90.00 _cell_angle_beta 98.048(8) _cell_angle_gamma 90.00 _cell_volume 2488.0(13) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1780 _cell_measurement_theta_min 2.64 _cell_measurement_theta_max 25.19 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.189 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 952 _exptl_absorpt_coefficient_mu 1.669 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7001 _exptl_absorpt_correction_T_max 0.8643 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 11670 _diffrn_reflns_av_R_equivalents 0.0795 _diffrn_reflns_av_sigmaI/netI 0.1092 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 25.31 _reflns_number_total 4448 _reflns_number_gt 2014 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0695P)^2^+0.4535P] 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 4448 _refine_ls_number_parameters 246 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1492 _refine_ls_R_factor_gt 0.0476 _refine_ls_wR_factor_ref 0.1508 _refine_ls_wR_factor_gt 0.1041 _refine_ls_goodness_of_fit_ref 0.889 _refine_ls_restrained_S_all 0.889 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.54654(2) 0.49472(9) 0.81202(4) 0.0601(2) Uani 1 1 d . . . C1 C 0.5600(2) 0.2405(8) 1.5662(4) 0.0698(18) Uani 1 1 d . . . H1A H 0.5317 0.1746 1.5245 0.105 Uiso 1 1 calc R . . H1B H 0.5444 0.2695 1.6266 0.105 Uiso 1 1 calc R . . H1C H 0.5960 0.1802 1.5833 0.105 Uiso 1 1 calc R . . C2 C 0.5800(2) 0.5438(7) 1.5500(4) 0.0554(17) Uani 1 1 d . . . H2 H 0.5777 0.5750 1.6159 0.066 Uiso 1 1 calc R . . C3 C 0.5793(2) 0.3951(8) 1.4143(4) 0.0526(15) Uani 1 1 d . . . H3 H 0.5770 0.3062 1.3709 0.063 Uiso 1 1 calc R . . C4 C 0.5920(2) 0.6427(7) 1.4742(4) 0.0536(14) Uani 1 1 d . . . H4 H 0.5999 0.7541 1.4782 0.064 Uiso 1 1 calc R . . C5 C 0.6042(2) 0.5993(7) 1.2924(3) 0.0500(14) Uani 1 1 d . . . H5A H 0.5866 0.7055 1.2762 0.060 Uiso 1 1 calc R . . H5B H 0.5874 0.5229 1.2410 0.060 Uiso 1 1 calc R . . C6 C 0.6692(2) 0.6094(7) 1.2928(4) 0.0499(14) Uani 1 1 d . . . C7 C 0.7445(2) 0.6453(9) 1.1919(4) 0.0665(18) Uani 1 1 d . . . H7A H 0.7657 0.5541 1.2261 0.080 Uiso 1 1 calc R . . H7B H 0.7601 0.7454 1.2238 0.080 Uiso 1 1 calc R . . C8 C 0.7528(2) 0.6456(8) 1.0830(4) 0.0600(16) Uani 1 1 d . . . H8A H 0.7327 0.7392 1.0497 0.072 Uiso 1 1 calc R . . H8B H 0.7354 0.5477 1.0507 0.072 Uiso 1 1 calc R . . C9 C 0.8179(2) 0.6526(8) 1.0722(4) 0.0577(16) Uani 1 1 d . . . H9A H 0.8348 0.7504 1.1053 0.069 Uiso 1 1 calc R . . H9B H 0.8376 0.5596 1.1070 0.069 Uiso 1 1 calc R . . C10 C 0.8311(2) 0.6525(8) 0.9649(4) 0.0600(16) Uani 1 1 d . . . H10A H 0.8134 0.5560 0.9312 0.072 Uiso 1 1 calc R . . H10B H 0.8123 0.7470 0.9305 0.072 Uiso 1 1 calc R . . C11 C 0.8958(2) 0.6553(8) 0.9544(4) 0.0575(16) Uani 1 1 d . . . H11A H 0.9147 0.5613 0.9891 0.069 Uiso 1 1 calc R . . H11B H 0.9135 0.7524 0.9873 0.069 Uiso 1 1 calc R . . C12 C 0.9083(2) 0.6535(8) 0.8458(4) 0.0579(16) Uani 1 1 d . . . H12A H 0.8900 0.5574 0.8126 0.069 Uiso 1 1 calc R . . H12B H 0.8898 0.7484 0.8114 0.069 Uiso 1 1 calc R . . C13 C 0.9735(2) 0.6535(8) 0.8343(4) 0.0577(16) Uani 1 1 d . . . H13A H 0.9920 0.7493 0.8675 0.069 Uiso 1 1 calc R . . H13B H 0.9920 0.5582 0.8681 0.069 Uiso 1 1 calc R . . C14 C 0.9851(2) 0.6527(8) 0.7259(3) 0.0588(16) Uani 1 1 d . . . H14A H 0.9669 0.5564 0.6929 0.071 Uiso 1 1 calc R . . H14B H 0.9662 0.7474 0.6920 0.071 Uiso 1 1 calc R . . C15 C 1.0496(2) 0.6542(8) 0.7135(4) 0.0551(15) Uani 1 1 d . . . H15A H 1.0686 0.5597 0.7476 0.066 Uiso 1 1 calc R . . H15B H 1.0678 0.7508 0.7461 0.066 Uiso 1 1 calc R . . C16 C 1.0613(2) 0.6525(8) 0.6045(4) 0.0594(17) Uani 1 1 d . . . H16A H 1.0428 0.5561 0.5720 0.071 Uiso 1 1 calc R . . H16B H 1.0422 0.7470 0.5706 0.071 Uiso 1 1 calc R . . C17 C 1.1255(2) 0.6535(8) 0.5899(3) 0.0550(16) Uani 1 1 d . . . H17A H 1.1445 0.5581 0.6229 0.066 Uiso 1 1 calc R . . H17B H 1.1442 0.7491 0.6231 0.066 Uiso 1 1 calc R . . C18 C 1.1367(2) 0.6541(8) 0.4816(4) 0.0551(15) Uani 1 1 d . . . H18A H 1.1182 0.5583 0.4483 0.066 Uiso 1 1 calc R . . H18B H 1.1178 0.7494 0.4485 0.066 Uiso 1 1 calc R . . C19 C 1.2013(2) 0.6552(8) 0.4681(4) 0.0597(17) Uani 1 1 d . . . H19A H 1.2203 0.5610 0.5024 0.072 Uiso 1 1 calc R . . H19B H 1.2196 0.7519 0.5005 0.072 Uiso 1 1 calc R . . C20 C 1.2127(2) 0.6529(8) 0.3600(4) 0.0595(16) Uani 1 1 d . . . H20A H 1.1939 0.5571 0.3273 0.071 Uiso 1 1 calc R . . H20B H 1.1943 0.7481 0.3260 0.071 Uiso 1 1 calc R . . C21 C 1.2772(2) 0.6515(9) 0.3469(4) 0.074(2) Uani 1 1 d . . . H21A H 1.2956 0.5568 0.3814 0.088 Uiso 1 1 calc R . . H21B H 1.2958 0.7477 0.3793 0.088 Uiso 1 1 calc R . . C22 C 1.2893(3) 0.6480(11) 0.2394(5) 0.099(3) Uani 1 1 d . . . H22A H 1.2708 0.5537 0.2062 0.149 Uiso 1 1 calc R . . H22B H 1.3312 0.6432 0.2383 0.149 Uiso 1 1 calc R . . H22C H 1.2736 0.7448 0.2054 0.149 Uiso 1 1 calc R . . N1 N 0.57204(17) 0.3902(6) 1.5113(3) 0.0504(12) Uani 1 1 d . . . N2 N 0.59025(18) 0.5460(5) 1.3905(3) 0.0458(12) Uani 1 1 d . . . O1 O 0.70505(16) 0.6022(7) 1.3653(3) 0.0817(15) Uani 1 1 d . . . O2 O 0.68183(14) 0.6316(5) 1.1994(2) 0.0565(11) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0726(4) 0.0535(4) 0.0570(3) -0.0035(4) 0.0190(2) 0.0038(4) C1 0.082(4) 0.067(5) 0.063(4) 0.017(4) 0.020(3) -0.015(4) C2 0.065(4) 0.061(5) 0.043(3) -0.007(3) 0.015(3) 0.003(3) C3 0.059(4) 0.055(5) 0.046(3) 0.007(3) 0.014(3) 0.000(3) C4 0.068(4) 0.048(4) 0.048(3) -0.002(3) 0.018(3) -0.004(3) C5 0.050(3) 0.064(4) 0.038(3) 0.003(3) 0.012(2) 0.003(3) C6 0.051(3) 0.056(4) 0.045(3) 0.002(3) 0.013(3) 0.002(3) C7 0.048(3) 0.101(6) 0.052(3) 0.006(4) 0.017(3) -0.006(3) C8 0.053(3) 0.081(5) 0.048(3) 0.000(3) 0.017(3) -0.003(3) C9 0.052(3) 0.078(5) 0.046(3) 0.001(3) 0.019(3) 0.001(3) C10 0.051(3) 0.085(5) 0.048(3) 0.004(3) 0.019(3) -0.004(3) C11 0.049(3) 0.075(5) 0.049(3) 0.000(3) 0.013(3) -0.003(3) C12 0.055(3) 0.078(5) 0.043(3) -0.003(3) 0.014(3) -0.003(3) C13 0.051(3) 0.075(5) 0.050(3) 0.000(3) 0.017(3) -0.004(3) C14 0.049(3) 0.085(5) 0.045(3) -0.003(3) 0.016(3) -0.005(3) C15 0.050(3) 0.068(4) 0.049(3) -0.001(3) 0.014(2) -0.002(3) C16 0.054(3) 0.082(5) 0.045(3) -0.005(3) 0.012(3) 0.000(3) C17 0.049(3) 0.076(5) 0.042(3) -0.003(3) 0.012(2) 0.002(3) C18 0.050(3) 0.072(5) 0.045(3) 0.003(3) 0.012(2) 0.001(3) C19 0.050(3) 0.082(5) 0.048(3) 0.001(3) 0.012(3) 0.006(3) C20 0.050(3) 0.080(5) 0.050(3) 0.002(3) 0.012(3) 0.004(3) C21 0.054(4) 0.105(6) 0.065(4) -0.005(4) 0.020(3) 0.001(4) C22 0.074(5) 0.153(9) 0.078(5) -0.003(5) 0.034(4) 0.006(5) N1 0.052(3) 0.052(4) 0.050(3) 0.002(3) 0.015(2) 0.001(2) N2 0.048(2) 0.052(4) 0.039(2) 0.001(2) 0.0096(19) 0.004(2) O1 0.053(2) 0.147(5) 0.046(2) 0.018(3) 0.0085(19) -0.008(3) O2 0.048(2) 0.082(3) 0.042(2) 0.007(2) 0.0169(16) 0.001(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 C1 N1 1.476(7) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C4 1.359(7) . ? C2 N1 1.365(7) . ? C2 H2 0.9300 . ? C3 N2 1.309(7) . ? C3 N1 1.338(6) . ? C3 H3 0.9300 . ? C4 N2 1.371(6) . ? C4 H4 0.9300 . ? C5 N2 1.465(6) . ? C5 C6 1.485(6) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 O1 1.183(6) . ? C6 O2 1.339(5) . ? C7 O2 1.453(5) . ? C7 C8 1.501(6) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.515(6) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.513(6) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.504(6) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.526(6) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.518(7) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.516(6) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.504(6) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.523(6) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.508(6) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.511(6) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.511(6) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.512(6) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.505(7) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C22 1.507(7) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? 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 N1 C1 H1A 109.5 . . ? N1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? N1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C4 C2 N1 107.2(5) . . ? C4 C2 H2 126.4 . . ? N1 C2 H2 126.4 . . ? N2 C3 N1 108.7(6) . . ? N2 C3 H3 125.7 . . ? N1 C3 H3 125.7 . . ? C2 C4 N2 106.5(5) . . ? C2 C4 H4 126.8 . . ? N2 C4 H4 126.8 . . ? N2 C5 C6 110.8(4) . . ? N2 C5 H5A 109.5 . . ? C6 C5 H5A 109.5 . . ? N2 C5 H5B 109.5 . . ? C6 C5 H5B 109.5 . . ? H5A C5 H5B 108.1 . . ? O1 C6 O2 124.3(5) . . ? O1 C6 C5 125.2(5) . . ? O2 C6 C5 110.5(4) . . ? O2 C7 C8 109.1(4) . . ? O2 C7 H7A 109.9 . . ? C8 C7 H7A 109.9 . . ? O2 C7 H7B 109.9 . . ? C8 C7 H7B 109.9 . . ? H7A C7 H7B 108.3 . . ? C7 C8 C9 110.7(4) . . ? C7 C8 H8A 109.5 . . ? C9 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? C9 C8 H8B 109.5 . . ? H8A C8 H8B 108.1 . . ? C10 C9 C8 114.8(4) . . ? C10 C9 H9A 108.6 . . ? C8 C9 H9A 108.6 . . ? C10 C9 H9B 108.6 . . ? C8 C9 H9B 108.6 . . ? H9A C9 H9B 107.5 . . ? C11 C10 C9 114.7(4) . . ? C11 C10 H10A 108.6 . . ? C9 C10 H10A 108.6 . . ? C11 C10 H10B 108.6 . . ? C9 C10 H10B 108.6 . . ? H10A C10 H10B 107.6 . . ? C10 C11 C12 114.0(4) . . ? C10 C11 H11A 108.7 . . ? C12 C11 H11A 108.7 . . ? C10 C11 H11B 108.7 . . ? C12 C11 H11B 108.7 . . ? H11A C11 H11B 107.6 . . ? C13 C12 C11 114.5(4) . . ? C13 C12 H12A 108.6 . . ? C11 C12 H12A 108.6 . . ? C13 C12 H12B 108.6 . . ? C11 C12 H12B 108.6 . . ? H12A C12 H12B 107.6 . . ? C14 C13 C12 113.8(4) . . ? C14 C13 H13A 108.8 . . ? C12 C13 H13A 108.8 . . ? C14 C13 H13B 108.8 . . ? C12 C13 H13B 108.8 . . ? H13A C13 H13B 107.7 . . ? C15 C14 C13 114.3(4) . . ? C15 C14 H14A 108.7 . . ? C13 C14 H14A 108.7 . . ? C15 C14 H14B 108.7 . . ? C13 C14 H14B 108.7 . . ? H14A C14 H14B 107.6 . . ? C14 C15 C16 114.3(4) . . ? C14 C15 H15A 108.7 . . ? C16 C15 H15A 108.7 . . ? C14 C15 H15B 108.7 . . ? C16 C15 H15B 108.7 . . ? H15A C15 H15B 107.6 . . ? C17 C16 C15 115.4(4) . . ? C17 C16 H16A 108.4 . . ? C15 C16 H16A 108.4 . . ? C17 C16 H16B 108.4 . . ? C15 C16 H16B 108.4 . . ? H16A C16 H16B 107.5 . . ? C16 C17 C18 115.1(4) . . ? C16 C17 H17A 108.5 . . ? C18 C17 H17A 108.5 . . ? C16 C17 H17B 108.5 . . ? C18 C17 H17B 108.5 . . ? H17A C17 H17B 107.5 . . ? C19 C18 C17 114.4(4) . . ? C19 C18 H18A 108.6 . . ? C17 C18 H18A 108.6 . . ? C19 C18 H18B 108.6 . . ? C17 C18 H18B 108.6 . . ? H18A C18 H18B 107.6 . . ? C18 C19 C20 114.7(4) . . ? C18 C19 H19A 108.6 . . ? C20 C19 H19A 108.6 . . ? C18 C19 H19B 108.6 . . ? C20 C19 H19B 108.6 . . ? H19A C19 H19B 107.6 . . ? C21 C20 C19 114.6(4) . . ? C21 C20 H20A 108.6 . . ? C19 C20 H20A 108.6 . . ? C21 C20 H20B 108.6 . . ? C19 C20 H20B 108.6 . . ? H20A C20 H20B 107.6 . . ? C20 C21 C22 115.2(5) . . ? C20 C21 H21A 108.5 . . ? C22 C21 H21A 108.5 . . ? C20 C21 H21B 108.5 . . ? C22 C21 H21B 108.5 . . ? H21A C21 H21B 107.5 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C3 N1 C2 108.3(5) . . ? C3 N1 C1 124.7(5) . . ? C2 N1 C1 126.9(4) . . ? C3 N2 C4 109.3(5) . . ? C3 N2 C5 125.0(5) . . ? C4 N2 C5 125.4(5) . . ? C6 O2 C7 114.8(4) . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 25.31 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.517 _refine_diff_density_min -0.483 _refine_diff_density_rms 0.061 _database_code_depnum_ccdc_archive 'CCDC 942009' ####################################################################### # # 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_test _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H41 B1 F4 N2 O2' _chemical_formula_weight 452.38 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' 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' H H 0.0000 0.0000 '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 8.4947(7) _cell_length_b 9.0566(7) _cell_length_c 32.905(3) _cell_angle_alpha 82.735(4) _cell_angle_beta 88.304(4) _cell_angle_gamma 88.047(4) _cell_volume 2508.9(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.201 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 976 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9118 _exptl_absorpt_correction_T_max 0.9671 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 32488 _diffrn_reflns_av_R_equivalents 0.0601 _diffrn_reflns_av_sigmaI/netI 0.0682 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 25.00 _reflns_number_total 8818 _reflns_number_gt 4607 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0117P)^2^+3.7266P] 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 8818 _refine_ls_number_parameters 563 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1447 _refine_ls_R_factor_gt 0.0748 _refine_ls_wR_factor_ref 0.1705 _refine_ls_wR_factor_gt 0.1430 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _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 O3 O 1.0719(3) 0.2507(3) 0.16042(8) 0.0619(8) Uani 1 1 d . . . O4 O 1.0220(3) 0.4253(3) 0.20194(7) 0.0485(6) Uani 1 1 d . . . O6 O 0.1371(4) 0.8708(4) 0.14913(9) 0.0856(10) Uani 1 1 d . . . O9 O 0.3656(3) 0.8963(3) 0.17924(7) 0.0545(7) Uani 1 1 d . . . N5 N 1.0988(4) 0.4582(3) 0.09360(9) 0.0465(7) Uani 1 1 d . . . N6 N 1.2130(4) 0.3823(3) 0.04031(9) 0.0512(8) Uani 1 1 d . . . N7 N 0.4951(4) 1.0408(3) 0.11123(9) 0.0510(8) Uani 1 1 d . . . N15 N 0.7367(4) 0.9888(4) 0.09458(9) 0.0565(9) Uani 1 1 d . . . C23 C 1.3350(5) 0.3493(5) 0.01018(13) 0.0785(14) Uani 1 1 d . . . H23A H 1.3266 0.2485 0.0046 0.118 Uiso 1 1 calc R . . H23B H 1.4370 0.3619 0.0209 0.118 Uiso 1 1 calc R . . H23C H 1.3216 0.4160 -0.0147 0.118 Uiso 1 1 calc R . . C24 C 1.2354(4) 0.4435(4) 0.07380(11) 0.0472(9) Uani 1 1 d . . . H24 H 1.3321 0.4719 0.0823 0.057 Uiso 1 1 calc R . . C25 C 1.0547(5) 0.3570(5) 0.03851(12) 0.0587(11) Uani 1 1 d . . . H25 H 1.0059 0.3156 0.0179 0.070 Uiso 1 1 calc R . . C26 C 0.9840(5) 0.4024(4) 0.07152(12) 0.0562(10) Uani 1 1 d . . . H26 H 0.8771 0.3975 0.0784 0.067 Uiso 1 1 calc R . . C27 C 1.0768(5) 0.5093(4) 0.13327(11) 0.0521(10) Uani 1 1 d . . . H27A H 0.9842 0.5750 0.1331 0.063 Uiso 1 1 calc R . . H27B H 1.1672 0.5653 0.1389 0.063 Uiso 1 1 calc R . . C28 C 1.0571(4) 0.3794(4) 0.16643(11) 0.0456(9) Uani 1 1 d . . . C29 C 0.9816(5) 0.3103(4) 0.23498(11) 0.0541(10) Uani 1 1 d . . . H29A H 1.0737 0.2478 0.2426 0.065 Uiso 1 1 calc R . . H29B H 0.9012 0.2482 0.2264 0.065 Uiso 1 1 calc R . . C30 C 0.9220(5) 0.3851(4) 0.27046(11) 0.0504(10) Uani 1 1 d . . . H30B H 0.8309 0.4479 0.2622 0.060 Uiso 1 1 calc R . . H30A H 1.0028 0.4489 0.2780 0.060 Uiso 1 1 calc R . . C31 C 0.8764(5) 0.2767(4) 0.30772(10) 0.0498(10) Uani 1 1 d . . . H31B H 0.7948 0.2137 0.3002 0.060 Uiso 1 1 calc R . . H31A H 0.9673 0.2130 0.3157 0.060 Uiso 1 1 calc R . . C32 C 0.8178(4) 0.3516(4) 0.34407(10) 0.0468(9) Uani 1 1 d . . . H32A H 0.8992 0.4155 0.3512 0.056 Uiso 1 1 calc R . . H32B H 0.7266 0.4146 0.3360 0.056 Uiso 1 1 calc R . . C33 C 0.7732(4) 0.2467(4) 0.38170(10) 0.0469(9) Uani 1 1 d . . . H33A H 0.8643 0.1838 0.3900 0.056 Uiso 1 1 calc R . . H33B H 0.6917 0.1826 0.3746 0.056 Uiso 1 1 calc R . . C34 C 0.7145(4) 0.3238(4) 0.41771(10) 0.0442(9) Uani 1 1 d . . . H34A H 0.6234 0.3866 0.4094 0.053 Uiso 1 1 calc R . . H34B H 0.7960 0.3881 0.4247 0.053 Uiso 1 1 calc R . . C35 C 0.6694(4) 0.2200(4) 0.45569(10) 0.0456(9) Uani 1 1 d . . . H35A H 0.7605 0.1572 0.4641 0.055 Uiso 1 1 calc R . . H35B H 0.5879 0.1557 0.4488 0.055 Uiso 1 1 calc R . . C36 C 0.6107(4) 0.2980(4) 0.49157(10) 0.0435(9) Uani 1 1 d . . . H36A H 0.5193 0.3603 0.4832 0.052 Uiso 1 1 calc R . . H36B H 0.6920 0.3628 0.4984 0.052 Uiso 1 1 calc R . . C37 C 0.5666(4) 0.1942(4) 0.52970(10) 0.0451(9) Uani 1 1 d . . . H37A H 0.4861 0.1287 0.5228 0.054 Uiso 1 1 calc R . . H37B H 0.6584 0.1326 0.5382 0.054 Uiso 1 1 calc R . . C38 C 0.5064(4) 0.2722(4) 0.56545(10) 0.0430(9) Uani 1 1 d . . . H38A H 0.4143 0.3335 0.5570 0.052 Uiso 1 1 calc R . . H38B H 0.5867 0.3380 0.5723 0.052 Uiso 1 1 calc R . . C39 C 0.4629(4) 0.1679(4) 0.60358(10) 0.0454(9) Uani 1 1 d . . . H39A H 0.3832 0.1017 0.5967 0.054 Uiso 1 1 calc R . . H39B H 0.5552 0.1072 0.6122 0.054 Uiso 1 1 calc R . . C40 C 0.4017(4) 0.2462(4) 0.63915(10) 0.0427(9) Uani 1 1 d . . . H40B H 0.3094 0.3068 0.6305 0.051 Uiso 1 1 calc R . . H40A H 0.4814 0.3127 0.6459 0.051 Uiso 1 1 calc R . . C41 C 0.3582(4) 0.1433(4) 0.67755(10) 0.0472(9) Uani 1 1 d . . . H41A H 0.2788 0.0764 0.6708 0.057 Uiso 1 1 calc R . . H41B H 0.4505 0.0831 0.6863 0.057 Uiso 1 1 calc R . . C42 C 0.2962(4) 0.2219(4) 0.71293(10) 0.0479(9) Uani 1 1 d . . . H42A H 0.3757 0.2890 0.7195 0.057 Uiso 1 1 calc R . . H42B H 0.2039 0.2821 0.7041 0.057 Uiso 1 1 calc R . . C43 C 0.2526(5) 0.1209(4) 0.75145(11) 0.0614(11) Uani 1 1 d . . . H43A H 0.3446 0.0606 0.7605 0.074 Uiso 1 1 calc R . . H43B H 0.1726 0.0540 0.7451 0.074 Uiso 1 1 calc R . . C44 C 0.1915(6) 0.2034(5) 0.78613(13) 0.0819(15) Uani 1 1 d . . . H44A H 0.2741 0.2612 0.7948 0.123 Uiso 1 1 calc R . . H44B H 0.1570 0.1332 0.8087 0.123 Uiso 1 1 calc R . . H44C H 0.1046 0.2684 0.7769 0.123 Uiso 1 1 calc R . . C67 C 0.8732(5) 0.9241(6) 0.07417(14) 0.0846(15) Uani 1 1 d . . . H67C H 0.9437 0.8765 0.0944 0.127 Uiso 1 1 calc R . . H67B H 0.9270 1.0015 0.0571 0.127 Uiso 1 1 calc R . . H67A H 0.8385 0.8521 0.0576 0.127 Uiso 1 1 calc R . . C68 C 0.5873(5) 0.9609(4) 0.08887(11) 0.0494(9) Uani 1 1 d . . . H68 H 0.5528 0.8951 0.0717 0.059 Uiso 1 1 calc R . . C69 C 0.7390(7) 1.0900(5) 0.12168(14) 0.0803(15) Uani 1 1 d . . . H69 H 0.8285 1.1296 0.1311 0.096 Uiso 1 1 calc R . . C70 C 0.5907(7) 1.1229(5) 0.13235(14) 0.0779(15) Uani 1 1 d . . . H70 H 0.5578 1.1888 0.1506 0.093 Uiso 1 1 calc R . . C71 C 0.3251(5) 1.0326(5) 0.11437(12) 0.0631(12) Uani 1 1 d . . . H71A H 0.2872 1.0055 0.0889 0.076 Uiso 1 1 calc R . . H71B H 0.2810 1.1308 0.1176 0.076 Uiso 1 1 calc R . . C72 C 0.2646(5) 0.9232(5) 0.14921(12) 0.0556(10) Uani 1 1 d . . . C73 C 0.3176(5) 0.7936(4) 0.21464(11) 0.0530(10) Uani 1 1 d . . . H73A H 0.4079 0.7331 0.2248 0.064 Uiso 1 1 calc R . . H73B H 0.2396 0.7278 0.2066 0.064 Uiso 1 1 calc R . . C74 C 0.2499(5) 0.8765(4) 0.24777(10) 0.0498(9) Uani 1 1 d . . . H74B H 0.1568 0.9332 0.2378 0.060 Uiso 1 1 calc R . . H74A H 0.3261 0.9464 0.2545 0.060 Uiso 1 1 calc R . . C75 C 0.2057(4) 0.7736(4) 0.28639(10) 0.0460(9) Uani 1 1 d . . . H75B H 0.1264 0.7066 0.2797 0.055 Uiso 1 1 calc R . . H75A H 0.2980 0.7136 0.2954 0.055 Uiso 1 1 calc R . . C76 C 0.1435(4) 0.8538(4) 0.32132(10) 0.0469(9) Uani 1 1 d . . . H76B H 0.0510 0.9135 0.3124 0.056 Uiso 1 1 calc R . . H76A H 0.2226 0.9211 0.3279 0.056 Uiso 1 1 calc R . . C77 C 0.1001(4) 0.7511(4) 0.35985(10) 0.0434(9) Uani 1 1 d . . . H77A H 0.0203 0.6845 0.3532 0.052 Uiso 1 1 calc R . . H77B H 0.1924 0.6906 0.3685 0.052 Uiso 1 1 calc R . . C78 C 0.0391(4) 0.8301(4) 0.39532(10) 0.0455(9) Uani 1 1 d . . . H78A H -0.0530 0.8908 0.3867 0.055 Uiso 1 1 calc R . . H78B H 0.1190 0.8963 0.4021 0.055 Uiso 1 1 calc R . . C79 C -0.0046(4) 0.7267(4) 0.43362(10) 0.0433(9) Uani 1 1 d . . . H79A H -0.0848 0.6608 0.4269 0.052 Uiso 1 1 calc R . . H79B H 0.0875 0.6656 0.4422 0.052 Uiso 1 1 calc R . . C80 C -0.0650(4) 0.8048(4) 0.46930(10) 0.0442(9) Uani 1 1 d . . . H80B H 0.0154 0.8706 0.4761 0.053 Uiso 1 1 calc R . . H80A H -0.1568 0.8662 0.4607 0.053 Uiso 1 1 calc R . . C81 C -0.1089(4) 0.7014(4) 0.50745(10) 0.0428(9) Uani 1 1 d . . . H81B H -0.1898 0.6363 0.5007 0.051 Uiso 1 1 calc R . . H81A H -0.0172 0.6395 0.5158 0.051 Uiso 1 1 calc R . . C82 C -0.1680(4) 0.7793(4) 0.54326(10) 0.0454(9) Uani 1 1 d . . . H82B H -0.0868 0.8441 0.5501 0.055 Uiso 1 1 calc R . . H82A H -0.2593 0.8417 0.5348 0.055 Uiso 1 1 calc R . . C83 C -0.2126(4) 0.6761(4) 0.58133(10) 0.0442(9) Uani 1 1 d . . . H83B H -0.1214 0.6136 0.5897 0.053 Uiso 1 1 calc R . . H83A H -0.2940 0.6115 0.5745 0.053 Uiso 1 1 calc R . . C84 C -0.2712(4) 0.7543(4) 0.61716(10) 0.0459(9) Uani 1 1 d . . . H84B H -0.1898 0.8191 0.6239 0.055 Uiso 1 1 calc R . . H84A H -0.3625 0.8167 0.6087 0.055 Uiso 1 1 calc R . . C85 C -0.3155(4) 0.6517(4) 0.65523(10) 0.0473(9) Uani 1 1 d . . . H85B H -0.2246 0.5885 0.6635 0.057 Uiso 1 1 calc R . . H85A H -0.3978 0.5877 0.6486 0.057 Uiso 1 1 calc R . . C86 C -0.3722(5) 0.7306(4) 0.69108(11) 0.0507(10) Uani 1 1 d . . . H86B H -0.2896 0.7944 0.6977 0.061 Uiso 1 1 calc R . . H86A H -0.4627 0.7941 0.6827 0.061 Uiso 1 1 calc R . . C87 C -0.4173(5) 0.6293(4) 0.72933(11) 0.0597(11) Uani 1 1 d . . . H87A H -0.3270 0.5655 0.7378 0.072 Uiso 1 1 calc R . . H87B H -0.5005 0.5659 0.7229 0.072 Uiso 1 1 calc R . . C88 C -0.4728(6) 0.7115(5) 0.76478(13) 0.0855(15) Uani 1 1 d . . . H88A H -0.3872 0.7656 0.7734 0.128 Uiso 1 1 calc R . . H88B H -0.5084 0.6411 0.7872 0.128 Uiso 1 1 calc R . . H88C H -0.5578 0.7797 0.7562 0.128 Uiso 1 1 calc R . . B2 B 0.2693(6) 0.8144(6) 0.01960(16) 0.0600(13) Uani 1 1 d . . . B4 B 0.6101(7) 0.5307(6) 0.13025(17) 0.0644(14) Uani 1 1 d . . . F5 F 0.3818(3) 0.7524(3) 0.04534(9) 0.1015(10) Uani 1 1 d . . . F6 F 0.2678(5) 0.9655(3) 0.01850(10) 0.1346(14) Uani 1 1 d . . . F7 F 0.1256(3) 0.7636(4) 0.03448(9) 0.1028(9) Uani 1 1 d . . . F8 F 0.2893(4) 0.7721(4) -0.01856(9) 0.1067(10) Uani 1 1 d . . . F13 F 0.6028(4) 0.4868(5) 0.09219(10) 0.1431(15) Uani 1 1 d . . . F14 F 0.4696(4) 0.5394(7) 0.14417(11) 0.201(3) Uani 1 1 d . . . F15 F 0.7089(3) 0.4365(3) 0.15367(8) 0.0812(8) Uani 1 1 d . . . F16 F 0.6823(6) 0.6583(4) 0.12207(19) 0.227(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O3 0.086(2) 0.0455(16) 0.0534(17) -0.0088(13) 0.0115(15) 0.0051(15) O4 0.0621(17) 0.0453(14) 0.0385(14) -0.0071(11) 0.0074(12) -0.0064(12) O6 0.068(2) 0.113(3) 0.073(2) 0.0022(19) -0.0097(18) -0.022(2) O9 0.0565(17) 0.0615(17) 0.0422(15) 0.0065(12) 0.0043(13) -0.0063(13) N5 0.0482(19) 0.0480(18) 0.0432(18) -0.0037(14) -0.0006(16) -0.0082(15) N6 0.056(2) 0.055(2) 0.0423(19) -0.0041(15) 0.0068(16) -0.0093(16) N7 0.070(2) 0.0396(17) 0.0414(18) -0.0011(14) 0.0080(17) -0.0020(17) N15 0.055(2) 0.066(2) 0.047(2) 0.0006(17) -0.0017(17) -0.0098(18) C23 0.081(3) 0.086(3) 0.070(3) -0.018(3) 0.025(3) -0.014(3) C24 0.046(2) 0.051(2) 0.043(2) 0.0015(18) 0.0004(19) -0.0082(18) C25 0.058(3) 0.074(3) 0.044(2) -0.004(2) -0.004(2) -0.019(2) C26 0.044(2) 0.071(3) 0.053(3) -0.002(2) -0.004(2) -0.012(2) C27 0.061(3) 0.048(2) 0.047(2) -0.0069(18) 0.0047(19) -0.0055(19) C28 0.044(2) 0.052(2) 0.041(2) -0.0067(18) 0.0041(17) -0.0013(18) C29 0.069(3) 0.049(2) 0.043(2) -0.0017(18) 0.008(2) -0.005(2) C30 0.060(3) 0.046(2) 0.045(2) -0.0084(17) 0.0082(19) -0.0061(19) C31 0.060(3) 0.044(2) 0.045(2) -0.0066(17) 0.0079(19) -0.0052(19) C32 0.056(2) 0.039(2) 0.045(2) -0.0073(17) 0.0088(18) -0.0057(18) C33 0.057(2) 0.039(2) 0.044(2) -0.0057(16) 0.0064(18) -0.0032(18) C34 0.053(2) 0.0346(19) 0.045(2) -0.0052(16) 0.0058(18) -0.0031(17) C35 0.054(2) 0.0360(19) 0.046(2) -0.0050(16) 0.0061(18) -0.0021(17) C36 0.049(2) 0.0350(19) 0.046(2) -0.0031(16) 0.0054(17) -0.0025(17) C37 0.053(2) 0.0360(19) 0.045(2) -0.0040(16) 0.0065(18) -0.0019(17) C38 0.050(2) 0.0362(19) 0.043(2) -0.0058(16) 0.0038(17) -0.0018(17) C39 0.055(2) 0.0363(19) 0.044(2) -0.0051(16) 0.0061(18) 0.0009(17) C40 0.048(2) 0.0359(19) 0.044(2) -0.0051(16) 0.0018(17) -0.0024(17) C41 0.054(2) 0.041(2) 0.046(2) -0.0028(17) 0.0034(18) -0.0019(18) C42 0.051(2) 0.048(2) 0.044(2) -0.0039(17) 0.0023(18) 0.0001(18) C43 0.065(3) 0.065(3) 0.051(2) 0.002(2) 0.009(2) 0.003(2) C44 0.088(4) 0.103(4) 0.051(3) -0.001(3) 0.017(2) 0.013(3) C67 0.047(3) 0.115(4) 0.087(4) 0.003(3) -0.003(2) 0.009(3) C68 0.053(3) 0.051(2) 0.045(2) -0.0093(18) -0.0005(19) 0.002(2) C69 0.105(4) 0.083(3) 0.056(3) -0.006(3) 0.001(3) -0.055(3) C70 0.125(5) 0.054(3) 0.059(3) -0.020(2) 0.017(3) -0.035(3) C71 0.065(3) 0.070(3) 0.049(2) 0.004(2) 0.011(2) 0.021(2) C72 0.059(3) 0.062(3) 0.044(2) -0.006(2) 0.005(2) 0.010(2) C73 0.060(3) 0.053(2) 0.042(2) 0.0061(18) 0.0083(19) -0.002(2) C74 0.059(2) 0.045(2) 0.043(2) 0.0004(17) 0.0031(19) -0.0047(19) C75 0.052(2) 0.041(2) 0.044(2) -0.0016(16) 0.0016(18) -0.0053(18) C76 0.058(2) 0.0371(19) 0.044(2) 0.0008(16) 0.0037(18) -0.0019(18) C77 0.050(2) 0.0364(19) 0.044(2) -0.0038(16) 0.0024(17) -0.0035(17) C78 0.054(2) 0.0369(19) 0.044(2) -0.0038(16) 0.0061(18) -0.0035(17) C79 0.050(2) 0.0339(19) 0.045(2) -0.0027(16) 0.0042(17) -0.0040(17) C80 0.053(2) 0.0334(19) 0.046(2) -0.0047(16) 0.0063(18) -0.0024(17) C81 0.050(2) 0.0347(19) 0.044(2) -0.0046(16) 0.0041(17) -0.0041(17) C82 0.054(2) 0.0353(19) 0.046(2) -0.0036(16) 0.0050(18) -0.0013(17) C83 0.052(2) 0.0357(19) 0.044(2) -0.0039(16) 0.0051(17) -0.0010(17) C84 0.054(2) 0.0369(19) 0.046(2) -0.0049(16) 0.0075(18) -0.0026(17) C85 0.053(2) 0.039(2) 0.049(2) -0.0050(17) 0.0065(18) -0.0012(18) C86 0.058(2) 0.042(2) 0.051(2) -0.0024(17) 0.0091(19) 0.0013(18) C87 0.076(3) 0.051(2) 0.051(2) -0.0037(19) 0.016(2) -0.007(2) C88 0.120(4) 0.076(3) 0.059(3) -0.009(2) 0.034(3) -0.009(3) B2 0.053(3) 0.069(3) 0.059(3) -0.009(3) -0.012(3) -0.005(3) B4 0.065(4) 0.053(3) 0.075(4) -0.003(3) -0.014(3) -0.009(3) F5 0.096(2) 0.092(2) 0.116(2) 0.0012(17) -0.0559(19) -0.0075(16) F6 0.221(4) 0.0588(18) 0.125(3) 0.0045(17) -0.069(3) -0.021(2) F7 0.0672(19) 0.135(3) 0.110(2) -0.0280(19) 0.0055(16) -0.0096(18) F8 0.103(2) 0.141(3) 0.081(2) -0.0361(19) -0.0021(17) 0.0049(19) F13 0.113(3) 0.227(4) 0.091(2) -0.038(3) -0.027(2) 0.061(3) F14 0.066(2) 0.421(8) 0.093(3) 0.026(3) 0.0110(19) 0.072(3) F15 0.0617(15) 0.0853(18) 0.0920(19) 0.0126(15) -0.0224(14) -0.0062(14) F16 0.218(5) 0.081(3) 0.369(7) 0.058(3) -0.149(5) -0.042(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 O3 C28 1.208(4) . ? O4 C28 1.312(4) . ? O4 C29 1.449(4) . ? O6 C72 1.197(5) . ? O9 C72 1.322(5) . ? O9 C73 1.453(4) . ? N5 C24 1.325(4) . ? N5 C26 1.379(4) . ? N5 C27 1.444(4) . ? N6 C24 1.316(4) . ? N6 C25 1.376(5) . ? N6 C23 1.463(5) . ? N7 C68 1.319(4) . ? N7 C70 1.378(5) . ? N7 C71 1.449(5) . ? N15 C68 1.325(5) . ? N15 C69 1.358(5) . ? N15 C67 1.465(5) . ? C25 C26 1.329(5) . ? C27 C28 1.510(5) . ? C29 C30 1.490(5) . ? C30 C31 1.520(5) . ? C31 C32 1.512(4) . ? C32 C33 1.510(5) . ? C33 C34 1.514(4) . ? C34 C35 1.514(4) . ? C35 C36 1.515(4) . ? C36 C37 1.515(4) . ? C37 C38 1.515(4) . ? C38 C39 1.516(4) . ? C39 C40 1.514(4) . ? C40 C41 1.516(5) . ? C41 C42 1.512(4) . ? C42 C43 1.511(5) . ? C43 C44 1.512(5) . ? C69 C70 1.331(6) . ? C71 C72 1.507(5) . ? C73 C74 1.491(5) . ? C74 C75 1.523(5) . ? C75 C76 1.509(4) . ? C76 C77 1.519(4) . ? C77 C78 1.514(4) . ? C78 C79 1.516(4) . ? C79 C80 1.514(4) . ? C80 C81 1.513(4) . ? C81 C82 1.513(4) . ? C82 C83 1.512(4) . ? C83 C84 1.514(4) . ? C84 C85 1.509(5) . ? C85 C86 1.513(5) . ? C86 C87 1.509(5) . ? C87 C88 1.516(5) . ? B2 F5 1.356(5) . ? B2 F8 1.363(5) . ? B2 F6 1.364(6) . ? B2 F7 1.374(6) . ? B4 F14 1.269(6) . ? B4 F16 1.321(6) . ? B4 F15 1.360(5) . ? B4 F13 1.365(6) . ? 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 C28 O4 C29 115.8(3) . . ? C72 O9 C73 116.9(3) . . ? C24 N5 C26 107.8(3) . . ? C24 N5 C27 125.9(3) . . ? C26 N5 C27 126.0(3) . . ? C24 N6 C25 107.9(3) . . ? C24 N6 C23 125.8(4) . . ? C25 N6 C23 126.3(3) . . ? C68 N7 C70 107.5(4) . . ? C68 N7 C71 124.7(3) . . ? C70 N7 C71 127.6(4) . . ? C68 N15 C69 107.7(4) . . ? C68 N15 C67 125.5(4) . . ? C69 N15 C67 126.8(4) . . ? N6 C24 N5 109.4(3) . . ? C26 C25 N6 107.8(3) . . ? C25 C26 N5 107.1(3) . . ? N5 C27 C28 110.8(3) . . ? O3 C28 O4 125.3(3) . . ? O3 C28 C27 123.6(3) . . ? O4 C28 C27 111.1(3) . . ? O4 C29 C30 107.7(3) . . ? C29 C30 C31 113.4(3) . . ? C32 C31 C30 113.7(3) . . ? C33 C32 C31 115.0(3) . . ? C32 C33 C34 114.2(3) . . ? C33 C34 C35 114.7(3) . . ? C34 C35 C36 114.4(3) . . ? C35 C36 C37 114.5(3) . . ? C38 C37 C36 114.4(3) . . ? C37 C38 C39 114.3(3) . . ? C40 C39 C38 114.2(3) . . ? C39 C40 C41 114.8(3) . . ? C42 C41 C40 114.6(3) . . ? C43 C42 C41 115.2(3) . . ? C42 C43 C44 113.7(3) . . ? N7 C68 N15 109.5(3) . . ? C70 C69 N15 108.1(4) . . ? C69 C70 N7 107.1(4) . . ? N7 C71 C72 114.6(3) . . ? O6 C72 O9 125.2(4) . . ? O6 C72 C71 122.3(4) . . ? O9 C72 C71 112.5(4) . . ? O9 C73 C74 110.7(3) . . ? C73 C74 C75 112.5(3) . . ? C76 C75 C74 114.1(3) . . ? C75 C76 C77 114.0(3) . . ? C78 C77 C76 114.6(3) . . ? C77 C78 C79 114.3(3) . . ? C80 C79 C78 114.6(3) . . ? C81 C80 C79 114.5(3) . . ? C82 C81 C80 114.6(3) . . ? C83 C82 C81 114.7(3) . . ? C82 C83 C84 114.6(3) . . ? C85 C84 C83 114.7(3) . . ? C84 C85 C86 114.4(3) . . ? C87 C86 C85 115.0(3) . . ? C86 C87 C88 113.8(3) . . ? F5 B2 F8 111.8(4) . . ? F5 B2 F6 109.6(4) . . ? F8 B2 F6 111.7(4) . . ? F5 B2 F7 108.3(4) . . ? F8 B2 F7 106.6(4) . . ? F6 B2 F7 108.7(4) . . ? F14 B4 F16 115.7(6) . . ? F14 B4 F15 115.3(5) . . ? F16 B4 F15 106.7(4) . . ? F14 B4 F13 107.0(5) . . ? F16 B4 F13 101.6(5) . . ? F15 B4 F13 109.6(4) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.610 _refine_diff_density_min -0.520 _refine_diff_density_rms 0.047 _database_code_depnum_ccdc_archive 'CCDC 942010'