# Electronic Supplementary Material (ESI) for Chemical Communications # 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_expb18 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H20 B2 N4' _chemical_formula_sum 'C16 H20 B2 N4' _chemical_formula_weight 289.98 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' _symmetry_cell_setting monoclinic _space_group_name_H-M_alt P21/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 10.1884(4) _cell_length_b 7.2885(3) _cell_length_c 9.9017(4) _cell_angle_alpha 90.00 _cell_angle_beta 96.650(2) _cell_angle_gamma 90.00 _cell_volume 730.33(5) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2266 _cell_measurement_theta_min 3.44 _cell_measurement_theta_max 27.53 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.319 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 308 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6587 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details 'SADABS V2008/1' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 kappa CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 6717 _diffrn_reflns_av_R_equivalents 0.0248 _diffrn_reflns_av_sigmaI/netI 0.0218 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.44 _diffrn_reflns_theta_max 27.57 _reflns_number_total 1689 _reflns_number_gt 1404 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex2' _computing_cell_refinement 'Bruker Apex2' _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^)+(0.0639P)^2^+0.1744P] 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 1689 _refine_ls_number_parameters 102 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0493 _refine_ls_R_factor_gt 0.0396 _refine_ls_wR_factor_ref 0.1156 _refine_ls_wR_factor_gt 0.1087 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _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 N1 N 0.49870(9) 0.03553(13) 0.80519(10) 0.0160(2) Uani 1 1 d . . . N2 N 0.31297(9) -0.05156(14) 1.00174(10) 0.0159(2) Uani 1 1 d . . . C1 C 0.57634(12) 0.02098(18) 0.68948(12) 0.0201(3) Uani 1 1 d . . . H1A H 0.5302 -0.0590 0.6199 0.030 Uiso 1 1 calc R . . H1B H 0.6634 -0.0309 0.7204 0.030 Uiso 1 1 calc R . . H1C H 0.5872 0.1431 0.6509 0.030 Uiso 1 1 calc R . . C2 C 0.21296(11) -0.13568(18) 1.07726(13) 0.0212(3) Uani 1 1 d . . . H2A H 0.1569 -0.2175 1.0169 0.032 Uiso 1 1 calc R . . H2B H 0.1584 -0.0395 1.1116 0.032 Uiso 1 1 calc R . . H2C H 0.2567 -0.2063 1.1538 0.032 Uiso 1 1 calc R . . C3 C 0.35999(11) 0.04959(15) 0.77187(12) 0.0161(3) Uani 1 1 d . . . C4 C 0.26968(11) 0.00638(16) 0.86739(12) 0.0164(3) Uani 1 1 d . . . C5 C 0.13460(12) 0.02213(17) 0.82419(13) 0.0213(3) Uani 1 1 d . . . H5 H 0.0735 -0.0074 0.8864 0.026 Uiso 1 1 calc R . . C6 C 0.08592(12) 0.07905(19) 0.69429(13) 0.0240(3) Uani 1 1 d . . . H6 H -0.0067 0.0877 0.6687 0.029 Uiso 1 1 calc R . . C7 C 0.17302(13) 0.12290(17) 0.60257(13) 0.0232(3) Uani 1 1 d . . . H7 H 0.1411 0.1627 0.5134 0.028 Uiso 1 1 calc R . . C8 C 0.30789(12) 0.10827(16) 0.64207(12) 0.0196(3) Uani 1 1 d . . . H8 H 0.3672 0.1394 0.5784 0.024 Uiso 1 1 calc R . . B1 B 0.55235(12) 0.02419(17) 0.94491(13) 0.0149(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 N1 0.0173(5) 0.0172(5) 0.0138(5) 0.0001(4) 0.0028(4) -0.0005(4) N2 0.0166(5) 0.0163(5) 0.0149(5) 0.0007(4) 0.0029(4) -0.0002(4) C1 0.0245(6) 0.0214(6) 0.0151(6) 0.0013(5) 0.0054(5) 0.0007(5) C2 0.0177(6) 0.0233(6) 0.0230(6) 0.0049(5) 0.0036(5) -0.0024(5) C3 0.0183(6) 0.0131(5) 0.0161(6) -0.0019(4) -0.0009(4) -0.0003(4) C4 0.0185(6) 0.0134(5) 0.0166(6) -0.0016(4) -0.0004(4) 0.0009(4) C5 0.0194(6) 0.0220(6) 0.0221(6) -0.0015(5) 0.0009(5) 0.0012(5) C6 0.0196(6) 0.0238(6) 0.0267(7) -0.0015(5) -0.0059(5) 0.0029(5) C7 0.0296(7) 0.0190(6) 0.0187(6) 0.0011(5) -0.0069(5) 0.0014(5) C8 0.0257(6) 0.0160(6) 0.0166(6) 0.0005(4) 0.0000(5) -0.0011(5) B1 0.0173(6) 0.0123(6) 0.0149(6) -0.0008(5) 0.0016(5) 0.0014(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C3 1.4172(15) . ? N1 B1 1.4298(16) . ? N1 C1 1.4695(14) . ? N2 C4 1.4166(15) . ? N2 B1 1.4261(16) 3_657 ? N2 C2 1.4662(14) . ? C3 C8 1.3995(17) . ? C3 C4 1.4289(16) . ? C4 C5 1.3979(16) . ? C5 C6 1.3873(18) . ? C6 C7 1.3788(19) . ? C7 C8 1.3885(17) . ? B1 N2 1.4261(16) 3_657 ? B1 B1 1.650(2) 3_657 ? 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 C3 N1 B1 119.25(9) . . ? C3 N1 C1 115.84(9) . . ? B1 N1 C1 124.76(10) . . ? C4 N2 B1 119.19(9) . 3_657 ? C4 N2 C2 116.39(9) . . ? B1 N2 C2 124.42(10) 3_657 . ? C8 C3 N1 119.86(10) . . ? C8 C3 C4 118.06(11) . . ? N1 C3 C4 122.08(10) . . ? C5 C4 N2 120.01(10) . . ? C5 C4 C3 117.78(11) . . ? N2 C4 C3 122.21(10) . . ? C6 C5 C4 122.81(12) . . ? C7 C6 C5 119.45(12) . . ? C6 C7 C8 119.22(11) . . ? C7 C8 C3 122.68(11) . . ? N2 B1 N1 126.44(10) 3_657 . ? N2 B1 B1 116.94(13) 3_657 3_657 ? N1 B1 B1 116.62(13) . 3_657 ? 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 B1 N1 C3 C8 163.32(11) . . . . ? C1 N1 C3 C8 -20.76(15) . . . . ? B1 N1 C3 C4 -16.35(16) . . . . ? C1 N1 C3 C4 159.57(11) . . . . ? B1 N2 C4 C5 -164.63(11) 3_657 . . . ? C2 N2 C4 C5 14.87(16) . . . . ? B1 N2 C4 C3 15.65(16) 3_657 . . . ? C2 N2 C4 C3 -164.85(11) . . . . ? C8 C3 C4 C5 1.20(16) . . . . ? N1 C3 C4 C5 -179.12(10) . . . . ? C8 C3 C4 N2 -179.08(10) . . . . ? N1 C3 C4 N2 0.60(17) . . . . ? N2 C4 C5 C6 179.64(11) . . . . ? C3 C4 C5 C6 -0.63(18) . . . . ? C4 C5 C6 C7 -0.1(2) . . . . ? C5 C6 C7 C8 0.31(19) . . . . ? C6 C7 C8 C3 0.32(18) . . . . ? N1 C3 C8 C7 179.23(11) . . . . ? C4 C3 C8 C7 -1.08(17) . . . . ? C3 N1 B1 N2 -164.57(11) . . . 3_657 ? C1 N1 B1 N2 19.90(18) . . . 3_657 ? C3 N1 B1 B1 15.04(18) . . . 3_657 ? C1 N1 B1 B1 -160.49(12) . . . 3_657 ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.57 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.467 _refine_diff_density_min -0.201 _refine_diff_density_rms 0.045 _database_code_depnum_ccdc_archive 'CCDC 945386' ####################################################################### # # 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_twin5 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 Al F36 O4, C16 H20 B2 N4' _chemical_formula_sum 'C32 H20 Al B2 F36 N4 O4' _chemical_formula_weight 1257.12 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' Al Al 0.0645 0.0514 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _space_group_name_H-M_alt P21/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 15.4396(11) _cell_length_b 14.1144(9) _cell_length_c 20.1020(12) _cell_angle_alpha 90.00 _cell_angle_beta 94.047(4) _cell_angle_gamma 90.00 _cell_volume 4369.7(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1376 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 22.34 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.911 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2476 _exptl_absorpt_coefficient_mu 0.246 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5733 _exptl_absorpt_correction_T_max 0.7465 _exptl_absorpt_process_details 'TWINABS V2008/1' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 kappa CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 15725 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0675 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.32 _diffrn_reflns_theta_max 32.83 _reflns_number_total 15725 _reflns_number_gt 11269 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex2' _computing_cell_refinement 'Bruker Apex2' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ShelXLE 586 (Huebschle, 2012)' _computing_publication_material 'ShelXLE 586 (Huebschle, 2012)' _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^)+(0.0539P)^2^+1.4338P] 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 15725 _refine_ls_number_parameters 718 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0881 _refine_ls_R_factor_gt 0.0516 _refine_ls_wR_factor_ref 0.1251 _refine_ls_wR_factor_gt 0.1106 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 N1 N 0.84447(12) 0.16569(13) 0.47000(9) 0.0156(4) Uani 1 1 d . . . N2 N 0.65530(12) 0.15275(13) 0.44781(9) 0.0154(4) Uani 1 1 d . . . B1 B 0.79496(16) 0.24040(18) 0.49641(12) 0.0160(5) Uani 1 1 d . . . C1 C 0.93414(15) 0.14279(17) 0.49349(12) 0.0214(5) Uani 1 1 d . . . H1A H 0.9488 0.1749 0.5360 0.032 Uiso 1 1 calc R . . H1B H 0.9737 0.1640 0.4604 0.032 Uiso 1 1 calc R . . H1C H 0.9399 0.0742 0.4997 0.032 Uiso 1 1 calc R . . C2 C 0.56503(14) 0.11908(17) 0.44975(12) 0.0196(5) Uani 1 1 d . . . H2A H 0.5650 0.0504 0.4569 0.029 Uiso 1 1 calc R . . H2B H 0.5326 0.1339 0.4073 0.029 Uiso 1 1 calc R . . H2C H 0.5376 0.1506 0.4863 0.029 Uiso 1 1 calc R . . C3 C 0.80381(14) 0.10416(15) 0.42320(10) 0.0152(4) Uani 1 1 d . . . C4 C 0.71112(14) 0.09687(15) 0.41308(11) 0.0157(4) Uani 1 1 d . . . C5 C 0.67672(15) 0.02899(16) 0.36705(11) 0.0198(5) Uani 1 1 d . . . H5 H 0.6155 0.0226 0.3602 0.024 Uiso 1 1 calc R . . C6 C 0.72880(16) -0.02811(17) 0.33181(12) 0.0228(5) Uani 1 1 d . . . H6 H 0.7035 -0.0731 0.3011 0.027 Uiso 1 1 calc R . . C7 C 0.81835(16) -0.02022(16) 0.34101(12) 0.0228(5) Uani 1 1 d . . . H7 H 0.8544 -0.0593 0.3162 0.027 Uiso 1 1 calc R . . C8 C 0.85492(15) 0.04385(16) 0.38582(11) 0.0190(4) Uani 1 1 d . . . H8 H 0.9164 0.0478 0.3919 0.023 Uiso 1 1 calc R . . N1A N 0.63943(12) 0.31052(13) 0.50723(9) 0.0154(4) Uani 1 1 d . . . N2A N 0.82880(12) 0.32049(13) 0.53291(9) 0.0163(4) Uani 1 1 d . . . B1A B 0.68895(16) 0.23434(18) 0.48271(11) 0.0154(5) Uani 1 1 d . . . C1A C 0.55014(15) 0.33385(17) 0.48165(12) 0.0205(5) Uani 1 1 d . . . H1AA H 0.5094 0.3145 0.5143 0.031 Uiso 1 1 calc R . . H1AB H 0.5364 0.3003 0.4395 0.031 Uiso 1 1 calc R . . H1AC H 0.5453 0.4023 0.4741 0.031 Uiso 1 1 calc R . . C2A C 0.91921(15) 0.35413(17) 0.53221(12) 0.0211(5) Uani 1 1 d . . . H2AA H 0.9520 0.3343 0.5734 0.032 Uiso 1 1 calc R . . H2AB H 0.9197 0.4234 0.5291 0.032 Uiso 1 1 calc R . . H2AC H 0.9459 0.3270 0.4937 0.032 Uiso 1 1 calc R . . C3A C 0.67958(15) 0.37277(15) 0.55384(11) 0.0169(4) Uani 1 1 d . . . C4A C 0.77172(15) 0.37668(16) 0.56715(11) 0.0168(4) Uani 1 1 d . . . C5A C 0.80609(16) 0.44163(17) 0.61512(12) 0.0239(5) Uani 1 1 d . . . H5A H 0.8671 0.4438 0.6249 0.029 Uiso 1 1 calc R . . C6A C 0.75432(17) 0.50190(18) 0.64814(13) 0.0282(5) Uani 1 1 d . . . H6A H 0.7794 0.5452 0.6801 0.034 Uiso 1 1 calc R . . C7A C 0.66472(17) 0.49923(18) 0.63454(13) 0.0271(5) Uani 1 1 d . . . H7A H 0.6286 0.5412 0.6571 0.033 Uiso 1 1 calc R . . C8A C 0.62839(16) 0.43641(17) 0.58879(12) 0.0224(5) Uani 1 1 d . . . H8A H 0.5671 0.4355 0.5802 0.027 Uiso 1 1 calc R . . Al1A Al 0.75448(4) 0.49751(4) 0.24727(3) 0.01122(12) Uani 1 1 d . . . F1 F 1.02076(9) 0.50131(10) 0.27468(8) 0.0279(3) Uani 1 1 d . . . F2 F 1.06723(9) 0.35873(11) 0.28843(8) 0.0303(3) Uani 1 1 d . . . F3 F 0.99616(10) 0.42612(12) 0.36430(8) 0.0360(4) Uani 1 1 d . . . F4 F 0.85277(10) 0.33745(12) 0.15755(8) 0.0358(4) Uani 1 1 d . . . F5 F 0.97879(10) 0.40269(12) 0.16220(7) 0.0349(4) Uani 1 1 d . . . F6 F 0.96508(11) 0.25815(12) 0.19482(9) 0.0411(4) Uani 1 1 d . . . F7 F 0.94327(10) 0.24109(11) 0.33151(9) 0.0403(4) Uani 1 1 d . . . F8 F 0.83989(10) 0.33230(12) 0.35904(8) 0.0357(4) Uani 1 1 d . . . F9 F 0.82219(9) 0.24458(10) 0.27170(8) 0.0308(3) Uani 1 1 d . . . F10 F 0.81758(10) 0.75963(10) 0.33344(9) 0.0376(4) Uani 1 1 d . . . F11 F 0.89369(9) 0.63432(10) 0.35059(8) 0.0298(3) Uani 1 1 d . . . F12 F 0.84912(10) 0.71173(12) 0.43390(8) 0.0400(4) Uani 1 1 d . . . F13 F 0.82752(11) 0.50873(12) 0.43098(8) 0.0401(4) Uani 1 1 d . . . F14 F 0.69273(12) 0.47706(11) 0.40983(9) 0.0419(4) Uani 1 1 d . . . F15 F 0.73100(13) 0.58399(13) 0.48214(8) 0.0460(5) Uani 1 1 d . . . F16 F 0.59332(10) 0.63314(11) 0.38361(9) 0.0344(4) Uani 1 1 d . . . F17 F 0.67316(11) 0.74712(12) 0.42419(8) 0.0397(4) Uani 1 1 d . . . F18 F 0.64468(9) 0.73556(11) 0.31860(8) 0.0325(4) Uani 1 1 d . . . F19 F 0.73216(11) 0.75804(10) 0.18962(8) 0.0354(4) Uani 1 1 d . . . F20 F 0.61976(10) 0.68377(12) 0.14811(9) 0.0414(4) Uani 1 1 d . . . F21 F 0.69728(12) 0.76531(11) 0.08416(9) 0.0405(4) Uani 1 1 d . . . F22 F 0.65115(10) 0.58062(11) 0.03860(7) 0.0343(4) Uani 1 1 d . . . F23 F 0.77531(11) 0.62897(11) 0.00926(7) 0.0349(4) Uani 1 1 d . . . F24 F 0.76288(12) 0.49024(10) 0.05159(7) 0.0355(4) Uani 1 1 d . . . F25 F 0.87208(10) 0.72579(11) 0.10538(8) 0.0338(4) Uani 1 1 d . . . F26 F 0.90341(10) 0.57719(12) 0.11218(9) 0.0368(4) Uani 1 1 d . . . F27 F 0.87862(9) 0.65511(11) 0.20066(7) 0.0300(3) Uani 1 1 d . . . F28 F 0.53425(10) 0.41564(12) 0.32520(7) 0.0326(4) Uani 1 1 d . . . F29 F 0.45582(9) 0.40465(11) 0.23236(8) 0.0296(3) Uani 1 1 d . . . F30 F 0.54872(9) 0.51830(10) 0.24806(8) 0.0303(3) Uani 1 1 d . . . F31 F 0.53025(10) 0.29823(11) 0.13284(7) 0.0326(4) Uani 1 1 d . . . F32 F 0.56693(10) 0.44512(10) 0.12774(7) 0.0296(3) Uani 1 1 d . . . F33 F 0.66402(10) 0.33638(11) 0.12601(7) 0.0306(3) Uani 1 1 d . . . F34 F 0.63646(9) 0.26118(10) 0.32201(7) 0.0292(3) Uani 1 1 d . . . F35 F 0.52193(10) 0.22964(11) 0.25951(9) 0.0353(4) Uani 1 1 d . . . F36 F 0.64837(10) 0.20326(10) 0.22455(8) 0.0330(4) Uani 1 1 d . . . O1 O 0.85852(10) 0.45506(11) 0.26193(9) 0.0203(3) Uani 1 1 d . . . O2 O 0.73393(10) 0.58015(11) 0.30652(8) 0.0193(3) Uani 1 1 d . . . O3 O 0.68626(10) 0.40073(10) 0.24909(8) 0.0155(3) Uani 1 1 d . . . O4 O 0.73672(10) 0.54953(11) 0.16992(7) 0.0188(3) Uani 1 1 d . . . C10 C 0.91327(14) 0.38062(15) 0.26519(11) 0.0158(4) Uani 1 1 d . . . C11 C 1.00088(15) 0.41709(17) 0.29848(12) 0.0210(5) Uani 1 1 d . . . C12 C 0.92768(16) 0.34319(18) 0.19419(13) 0.0253(5) Uani 1 1 d . . . C13 C 0.87923(16) 0.29824(17) 0.30728(13) 0.0243(5) Uani 1 1 d . . . C14 C 0.74352(15) 0.62177(15) 0.36676(10) 0.0155(4) Uani 1 1 d . . . C15 C 0.82735(16) 0.68317(16) 0.37147(13) 0.0228(5) Uani 1 1 d . . . C16 C 0.74843(19) 0.54790(19) 0.42382(13) 0.0295(6) Uani 1 1 d . . . C17 C 0.66296(16) 0.68630(17) 0.37357(12) 0.0234(5) Uani 1 1 d . . . C18 C 0.75671(14) 0.61819(15) 0.12715(10) 0.0148(4) Uani 1 1 d . . . C19 C 0.70071(17) 0.70817(18) 0.13730(13) 0.0267(5) Uani 1 1 d . . . C20 C 0.73662(17) 0.57951(17) 0.05539(11) 0.0232(5) Uani 1 1 d . . . C21 C 0.85398(16) 0.64549(17) 0.13625(12) 0.0222(5) Uani 1 1 d . . . C22 C 0.60694(14) 0.36484(15) 0.23078(10) 0.0144(4) Uani 1 1 d . . . C23 C 0.53522(15) 0.42649(17) 0.25911(12) 0.0215(5) Uani 1 1 d . . . C24 C 0.59170(16) 0.36108(17) 0.15346(11) 0.0217(5) Uani 1 1 d . . . C25 C 0.60290(15) 0.26273(16) 0.25927(12) 0.0215(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0123(9) 0.0189(9) 0.0155(8) 0.0017(7) 0.0009(7) 0.0008(7) N2 0.0121(9) 0.0186(9) 0.0156(8) 0.0017(7) 0.0018(7) 0.0005(7) B1 0.0168(12) 0.0177(12) 0.0133(10) 0.0030(9) -0.0001(9) 0.0018(9) C1 0.0147(11) 0.0259(12) 0.0233(11) -0.0014(10) 0.0002(9) 0.0056(9) C2 0.0134(11) 0.0252(12) 0.0203(11) -0.0018(9) 0.0017(9) -0.0028(9) C3 0.0161(11) 0.0166(10) 0.0132(9) 0.0027(8) 0.0027(8) -0.0004(8) C4 0.0153(11) 0.0166(10) 0.0154(10) 0.0035(8) 0.0019(8) 0.0025(8) C5 0.0159(11) 0.0220(11) 0.0211(11) -0.0001(9) -0.0005(9) -0.0005(9) C6 0.0258(13) 0.0207(11) 0.0218(11) -0.0040(9) 0.0020(10) -0.0027(10) C7 0.0256(13) 0.0181(11) 0.0254(12) -0.0013(9) 0.0082(10) 0.0010(9) C8 0.0156(11) 0.0196(11) 0.0221(11) 0.0005(9) 0.0043(9) 0.0032(9) N1A 0.0134(9) 0.0181(9) 0.0149(8) 0.0032(7) 0.0018(7) 0.0002(7) N2A 0.0137(9) 0.0192(9) 0.0161(9) 0.0016(7) 0.0008(7) -0.0001(7) B1A 0.0162(12) 0.0192(12) 0.0108(10) 0.0048(9) 0.0012(9) 0.0014(9) C1A 0.0154(11) 0.0249(12) 0.0213(11) 0.0002(9) 0.0013(9) 0.0052(9) C2A 0.0141(11) 0.0250(12) 0.0240(11) -0.0020(10) 0.0006(9) -0.0027(9) C3A 0.0188(11) 0.0169(11) 0.0155(10) 0.0016(8) 0.0042(8) -0.0003(8) C4A 0.0182(11) 0.0193(11) 0.0131(9) 0.0011(8) 0.0031(8) 0.0013(8) C5A 0.0219(12) 0.0262(12) 0.0233(12) -0.0029(10) -0.0004(9) -0.0018(10) C6A 0.0326(14) 0.0267(13) 0.0254(12) -0.0089(10) 0.0029(11) -0.0035(11) C7A 0.0315(14) 0.0244(12) 0.0267(12) -0.0042(10) 0.0119(11) 0.0020(11) C8A 0.0201(12) 0.0240(12) 0.0239(12) -0.0004(10) 0.0062(9) 0.0006(9) Al1A 0.0114(3) 0.0122(3) 0.0101(3) 0.0003(2) 0.0009(2) -0.0001(2) F1 0.0180(7) 0.0243(7) 0.0412(9) 0.0025(7) -0.0004(6) -0.0048(6) F2 0.0120(7) 0.0348(8) 0.0439(9) 0.0094(7) 0.0014(6) 0.0064(6) F3 0.0292(9) 0.0569(11) 0.0213(7) -0.0041(7) -0.0030(6) -0.0085(8) F4 0.0279(8) 0.0544(10) 0.0245(8) -0.0117(7) -0.0034(6) -0.0065(7) F5 0.0287(8) 0.0549(10) 0.0221(7) 0.0035(7) 0.0086(6) -0.0065(7) F6 0.0356(9) 0.0354(9) 0.0534(10) -0.0186(8) 0.0115(8) 0.0094(7) F7 0.0231(8) 0.0369(9) 0.0602(11) 0.0291(8) -0.0014(8) 0.0038(7) F8 0.0317(9) 0.0487(10) 0.0281(8) 0.0067(7) 0.0126(7) -0.0043(7) F9 0.0215(7) 0.0188(7) 0.0518(10) 0.0026(7) 0.0003(7) -0.0028(6) F10 0.0318(8) 0.0216(8) 0.0592(11) 0.0078(8) 0.0022(8) -0.0046(6) F11 0.0152(7) 0.0320(8) 0.0421(9) -0.0079(7) 0.0009(6) -0.0005(6) F12 0.0306(9) 0.0465(10) 0.0410(9) -0.0261(8) -0.0105(7) -0.0039(7) F13 0.0436(10) 0.0370(9) 0.0382(9) 0.0104(7) -0.0076(7) 0.0126(8) F14 0.0507(11) 0.0315(9) 0.0437(10) 0.0133(8) 0.0057(8) -0.0139(8) F15 0.0664(13) 0.0554(11) 0.0166(7) 0.0034(7) 0.0072(8) 0.0022(9) F16 0.0193(8) 0.0419(9) 0.0437(9) -0.0103(8) 0.0135(7) -0.0021(7) F17 0.0362(9) 0.0398(9) 0.0429(9) -0.0261(8) 0.0016(8) 0.0097(7) F18 0.0262(8) 0.0320(8) 0.0384(9) 0.0044(7) -0.0034(7) 0.0115(6) F19 0.0498(10) 0.0243(8) 0.0322(8) -0.0110(7) 0.0034(7) 0.0018(7) F20 0.0200(8) 0.0462(10) 0.0583(11) -0.0072(9) 0.0049(8) 0.0087(7) F21 0.0554(11) 0.0237(8) 0.0411(9) 0.0093(7) -0.0070(8) 0.0105(7) F22 0.0351(9) 0.0408(9) 0.0250(7) 0.0028(7) -0.0113(6) -0.0129(7) F23 0.0512(10) 0.0387(9) 0.0152(7) 0.0056(6) 0.0060(7) -0.0107(7) F24 0.0605(11) 0.0233(8) 0.0233(7) -0.0068(6) 0.0066(7) 0.0010(7) F25 0.0338(9) 0.0331(9) 0.0342(8) 0.0137(7) -0.0002(7) -0.0171(7) F26 0.0210(8) 0.0435(9) 0.0477(10) 0.0047(8) 0.0140(7) 0.0059(7) F27 0.0252(8) 0.0367(9) 0.0268(8) 0.0067(7) -0.0083(6) -0.0133(6) F28 0.0248(8) 0.0542(10) 0.0195(7) -0.0034(7) 0.0058(6) 0.0060(7) F29 0.0129(7) 0.0419(9) 0.0334(8) 0.0015(7) -0.0026(6) 0.0008(6) F30 0.0270(8) 0.0220(7) 0.0414(9) -0.0032(6) -0.0007(7) 0.0067(6) F31 0.0325(9) 0.0411(9) 0.0237(7) -0.0061(7) -0.0032(6) -0.0196(7) F32 0.0308(8) 0.0357(8) 0.0211(7) 0.0118(6) -0.0054(6) -0.0069(6) F33 0.0291(8) 0.0428(9) 0.0211(7) -0.0096(7) 0.0096(6) -0.0067(7) F34 0.0287(8) 0.0309(8) 0.0270(7) 0.0157(6) -0.0036(6) -0.0052(6) F35 0.0226(8) 0.0338(9) 0.0487(9) 0.0145(8) -0.0022(7) -0.0155(6) F36 0.0354(9) 0.0170(7) 0.0463(9) -0.0046(7) 0.0006(7) -0.0004(6) O1 0.0115(7) 0.0146(8) 0.0348(9) -0.0006(7) 0.0014(7) 0.0020(6) O2 0.0188(8) 0.0224(8) 0.0166(7) -0.0086(6) 0.0017(6) 0.0007(6) O3 0.0131(7) 0.0151(7) 0.0181(7) 0.0017(6) -0.0009(6) -0.0024(6) O4 0.0198(8) 0.0227(8) 0.0135(7) 0.0064(6) -0.0008(6) -0.0065(6) C10 0.0130(10) 0.0162(10) 0.0182(10) -0.0001(8) 0.0017(8) 0.0017(8) C11 0.0150(11) 0.0240(12) 0.0238(11) 0.0027(10) 0.0000(9) 0.0019(9) C12 0.0192(12) 0.0301(13) 0.0268(12) -0.0048(11) 0.0030(10) 0.0005(10) C13 0.0170(12) 0.0254(12) 0.0303(13) 0.0061(10) 0.0002(10) 0.0015(9) C14 0.0179(11) 0.0150(10) 0.0134(9) -0.0015(8) 0.0004(8) 0.0009(8) C15 0.0200(12) 0.0194(12) 0.0286(12) -0.0073(10) -0.0008(10) 0.0015(9) C16 0.0374(15) 0.0289(14) 0.0219(12) 0.0050(10) 0.0002(11) 0.0006(12) C17 0.0212(12) 0.0253(12) 0.0237(12) -0.0076(10) 0.0022(10) 0.0021(10) C18 0.0176(11) 0.0140(10) 0.0129(9) 0.0012(8) 0.0006(8) -0.0019(8) C19 0.0271(14) 0.0248(12) 0.0277(13) 0.0002(10) -0.0002(10) 0.0061(10) C20 0.0325(14) 0.0221(12) 0.0151(10) 0.0023(9) 0.0025(9) -0.0034(10) C21 0.0208(12) 0.0232(12) 0.0230(11) 0.0058(9) 0.0034(10) -0.0038(9) C22 0.0137(10) 0.0154(10) 0.0139(10) 0.0013(8) 0.0008(8) -0.0034(8) C23 0.0156(11) 0.0256(12) 0.0230(11) 0.0007(10) 0.0006(9) 0.0010(9) C24 0.0200(12) 0.0289(13) 0.0163(10) -0.0035(9) 0.0011(9) -0.0081(10) C25 0.0188(12) 0.0196(11) 0.0257(12) 0.0029(9) -0.0009(9) -0.0060(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C3 1.396(3) . ? N1 B1 1.427(3) . ? N1 C1 1.467(3) . ? N2 C4 1.392(3) . ? N2 B1A 1.427(3) . ? N2 C2 1.476(3) . ? B1 N2A 1.427(3) . ? B1 B1A 1.643(3) . ? C3 C8 1.413(3) . ? C3 C4 1.435(3) . ? C4 C5 1.410(3) . ? C5 C6 1.370(3) . ? C6 C7 1.386(3) . ? C7 C8 1.370(3) . ? N1A C3A 1.397(3) . ? N1A B1A 1.427(3) . ? N1A C1A 1.474(3) . ? N2A C4A 1.402(3) . ? N2A C2A 1.475(3) . ? C3A C8A 1.415(3) . ? C3A C4A 1.430(3) . ? C4A C5A 1.407(3) . ? C5A C6A 1.370(4) . ? C6A C7A 1.392(4) . ? C7A C8A 1.369(3) . ? Al1A O2 1.7125(16) . ? Al1A O1 1.7203(16) . ? Al1A O4 1.7239(15) . ? Al1A O3 1.7268(15) . ? F1 C11 1.325(3) . ? F2 C11 1.341(3) . ? F3 C11 1.336(3) . ? F4 C12 1.329(3) . ? F5 C12 1.347(3) . ? F6 C12 1.332(3) . ? F7 C13 1.341(3) . ? F8 C13 1.331(3) . ? F9 C13 1.331(3) . ? F10 C15 1.325(3) . ? F11 C15 1.327(3) . ? F12 C15 1.338(3) . ? F13 C16 1.339(3) . ? F14 C16 1.336(3) . ? F15 C16 1.323(3) . ? F16 C17 1.338(3) . ? F17 C17 1.332(3) . ? F18 C17 1.319(3) . ? F19 C19 1.329(3) . ? F20 C19 1.329(3) . ? F21 C19 1.337(3) . ? F22 C20 1.339(3) . ? F23 C20 1.335(3) . ? F24 C20 1.327(3) . ? F25 C21 1.331(3) . ? F26 C21 1.341(3) . ? F27 C21 1.330(3) . ? F28 C23 1.338(3) . ? F29 C23 1.339(3) . ? F30 C23 1.334(3) . ? F31 C24 1.343(3) . ? F32 C24 1.339(3) . ? F33 C24 1.326(3) . ? F34 C25 1.329(3) . ? F35 C25 1.335(3) . ? F36 C25 1.324(3) . ? O1 C10 1.347(3) . ? O2 C14 1.345(3) . ? O3 C22 1.352(2) . ? O4 C18 1.346(2) . ? C10 C13 1.551(3) . ? C10 C12 1.553(3) . ? C10 C11 1.554(3) . ? C14 C16 1.548(3) . ? C14 C15 1.555(3) . ? C14 C17 1.555(3) . ? C18 C21 1.549(3) . ? C18 C20 1.553(3) . ? C18 C19 1.558(3) . ? C22 C23 1.548(3) . ? C22 C25 1.554(3) . ? C22 C24 1.557(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 N1 B1 118.89(18) . . ? C3 N1 C1 116.69(18) . . ? B1 N1 C1 124.15(18) . . ? C4 N2 B1A 119.14(19) . . ? C4 N2 C2 116.76(18) . . ? B1A N2 C2 123.96(19) . . ? N2A B1 N1 126.2(2) . . ? N2A B1 B1A 116.9(2) . . ? N1 B1 B1A 116.9(2) . . ? N1 C3 C8 119.4(2) . . ? N1 C3 C4 122.5(2) . . ? C8 C3 C4 118.1(2) . . ? N2 C4 C5 119.8(2) . . ? N2 C4 C3 122.35(19) . . ? C5 C4 C3 117.9(2) . . ? C6 C5 C4 122.1(2) . . ? C5 C6 C7 120.0(2) . . ? C8 C7 C6 120.1(2) . . ? C7 C8 C3 121.9(2) . . ? C3A N1A B1A 118.83(19) . . ? C3A N1A C1A 116.95(18) . . ? B1A N1A C1A 123.95(18) . . ? C4A N2A B1 118.74(19) . . ? C4A N2A C2A 116.78(18) . . ? B1 N2A C2A 124.2(2) . . ? N1A B1A N2 126.3(2) . . ? N1A B1A B1 117.0(2) . . ? N2 B1A B1 116.6(2) . . ? N1A C3A C8A 119.7(2) . . ? N1A C3A C4A 122.6(2) . . ? C8A C3A C4A 117.8(2) . . ? N2A C4A C5A 119.0(2) . . ? N2A C4A C3A 122.5(2) . . ? C5A C4A C3A 118.4(2) . . ? C6A C5A C4A 122.1(2) . . ? C5A C6A C7A 119.6(2) . . ? C8A C7A C6A 120.3(2) . . ? C7A C8A C3A 121.9(2) . . ? O2 Al1A O1 109.55(8) . . ? O2 Al1A O4 108.16(8) . . ? O1 Al1A O4 112.95(9) . . ? O2 Al1A O3 112.38(8) . . ? O1 Al1A O3 106.53(8) . . ? O4 Al1A O3 107.31(8) . . ? C10 O1 Al1A 148.77(15) . . ? C14 O2 Al1A 155.48(15) . . ? C22 O3 Al1A 146.38(14) . . ? C18 O4 Al1A 148.64(14) . . ? O1 C10 C13 112.05(19) . . ? O1 C10 C12 110.53(18) . . ? C13 C10 C12 108.81(19) . . ? O1 C10 C11 106.66(18) . . ? C13 C10 C11 109.37(18) . . ? C12 C10 C11 109.37(19) . . ? F1 C11 F3 107.6(2) . . ? F1 C11 F2 107.32(19) . . ? F3 C11 F2 107.66(19) . . ? F1 C11 C10 111.00(18) . . ? F3 C11 C10 110.57(19) . . ? F2 C11 C10 112.50(19) . . ? F4 C12 F6 108.1(2) . . ? F4 C12 F5 106.8(2) . . ? F6 C12 F5 107.4(2) . . ? F4 C12 C10 110.8(2) . . ? F6 C12 C10 112.8(2) . . ? F5 C12 C10 110.7(2) . . ? F8 C13 F9 107.7(2) . . ? F8 C13 F7 107.4(2) . . ? F9 C13 F7 107.2(2) . . ? F8 C13 C10 110.3(2) . . ? F9 C13 C10 111.7(2) . . ? F7 C13 C10 112.3(2) . . ? O2 C14 C16 111.69(18) . . ? O2 C14 C15 109.67(19) . . ? C16 C14 C15 109.46(19) . . ? O2 C14 C17 107.30(18) . . ? C16 C14 C17 109.1(2) . . ? C15 C14 C17 109.61(18) . . ? F10 C15 F11 107.4(2) . . ? F10 C15 F12 107.86(19) . . ? F11 C15 F12 107.74(19) . . ? F10 C15 C14 111.00(19) . . ? F11 C15 C14 110.42(18) . . ? F12 C15 C14 112.2(2) . . ? F15 C16 F14 107.8(2) . . ? F15 C16 F13 107.7(2) . . ? F14 C16 F13 106.4(2) . . ? F15 C16 C14 113.3(2) . . ? F14 C16 C14 110.5(2) . . ? F13 C16 C14 110.8(2) . . ? F18 C17 F17 107.88(19) . . ? F18 C17 F16 107.2(2) . . ? F17 C17 F16 107.4(2) . . ? F18 C17 C14 111.1(2) . . ? F17 C17 C14 113.12(19) . . ? F16 C17 C14 109.93(19) . . ? O4 C18 C21 111.58(17) . . ? O4 C18 C20 107.49(17) . . ? C21 C18 C20 109.01(19) . . ? O4 C18 C19 110.42(19) . . ? C21 C18 C19 108.92(18) . . ? C20 C18 C19 109.39(18) . . ? F19 C19 F20 107.7(2) . . ? F19 C19 F21 107.7(2) . . ? F20 C19 F21 107.6(2) . . ? F19 C19 C18 111.12(19) . . ? F20 C19 C18 110.3(2) . . ? F21 C19 C18 112.2(2) . . ? F24 C20 F23 107.6(2) . . ? F24 C20 F22 107.2(2) . . ? F23 C20 F22 107.47(19) . . ? F24 C20 C18 110.20(19) . . ? F23 C20 C18 113.05(19) . . ? F22 C20 C18 111.0(2) . . ? F27 C21 F25 108.2(2) . . ? F27 C21 F26 107.1(2) . . ? F25 C21 F26 107.5(2) . . ? F27 C21 C18 110.40(19) . . ? F25 C21 C18 112.98(19) . . ? F26 C21 C18 110.51(19) . . ? O3 C22 C23 110.30(18) . . ? O3 C22 C25 107.84(17) . . ? C23 C22 C25 109.72(19) . . ? O3 C22 C24 110.78(19) . . ? C23 C22 C24 108.96(18) . . ? C25 C22 C24 109.22(18) . . ? F30 C23 F28 106.8(2) . . ? F30 C23 F29 107.82(18) . . ? F28 C23 F29 107.3(2) . . ? F30 C23 C22 111.14(19) . . ? F28 C23 C22 111.05(19) . . ? F29 C23 C22 112.40(19) . . ? F33 C24 F32 107.34(19) . . ? F33 C24 F31 107.17(19) . . ? F32 C24 F31 106.84(19) . . ? F33 C24 C22 110.61(19) . . ? F32 C24 C22 112.0(2) . . ? F31 C24 C22 112.61(19) . . ? F36 C25 F34 107.69(19) . . ? F36 C25 F35 108.16(19) . . ? F34 C25 F35 107.0(2) . . ? F36 C25 C22 110.93(19) . . ? F34 C25 C22 109.98(18) . . ? F35 C25 C22 112.82(19) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 N1 B1 N2A -165.8(2) . . . . ? C1 N1 B1 N2A 20.4(4) . . . . ? C3 N1 B1 B1A 13.4(3) . . . . ? C1 N1 B1 B1A -160.3(2) . . . . ? B1 N1 C3 C8 166.0(2) . . . . ? C1 N1 C3 C8 -19.8(3) . . . . ? B1 N1 C3 C4 -16.4(3) . . . . ? C1 N1 C3 C4 157.8(2) . . . . ? B1A N2 C4 C5 -166.3(2) . . . . ? C2 N2 C4 C5 17.8(3) . . . . ? B1A N2 C4 C3 15.0(3) . . . . ? C2 N2 C4 C3 -160.9(2) . . . . ? N1 C3 C4 N2 2.0(3) . . . . ? C8 C3 C4 N2 179.59(19) . . . . ? N1 C3 C4 C5 -176.8(2) . . . . ? C8 C3 C4 C5 0.8(3) . . . . ? N2 C4 C5 C6 -179.7(2) . . . . ? C3 C4 C5 C6 -0.9(3) . . . . ? C4 C5 C6 C7 0.1(4) . . . . ? C5 C6 C7 C8 0.7(4) . . . . ? C6 C7 C8 C3 -0.8(4) . . . . ? N1 C3 C8 C7 177.6(2) . . . . ? C4 C3 C8 C7 0.0(3) . . . . ? N1 B1 N2A C4A -166.8(2) . . . . ? B1A B1 N2A C4A 14.0(3) . . . . ? N1 B1 N2A C2A 19.2(3) . . . . ? B1A B1 N2A C2A -160.0(2) . . . . ? C3A N1A B1A N2 164.5(2) . . . . ? C1A N1A B1A N2 -21.7(3) . . . . ? C3A N1A B1A B1 -14.9(3) . . . . ? C1A N1A B1A B1 158.9(2) . . . . ? C4 N2 B1A N1A 164.3(2) . . . . ? C2 N2 B1A N1A -20.1(3) . . . . ? C4 N2 B1A B1 -16.2(3) . . . . ? C2 N2 B1A B1 159.3(2) . . . . ? N2A B1 B1A N1A 1.2(3) . . . . ? N1 B1 B1A N1A -178.07(19) . . . . ? N2A B1 B1A N2 -178.28(19) . . . . ? N1 B1 B1A N2 2.4(3) . . . . ? B1A N1A C3A C8A -167.2(2) . . . . ? C1A N1A C3A C8A 18.6(3) . . . . ? B1A N1A C3A C4A 14.1(3) . . . . ? C1A N1A C3A C4A -160.1(2) . . . . ? B1 N2A C4A C5A 165.5(2) . . . . ? C2A N2A C4A C5A -20.1(3) . . . . ? B1 N2A C4A C3A -16.5(3) . . . . ? C2A N2A C4A C3A 158.0(2) . . . . ? N1A C3A C4A N2A 2.1(3) . . . . ? C8A C3A C4A N2A -176.6(2) . . . . ? N1A C3A C4A C5A -179.9(2) . . . . ? C8A C3A C4A C5A 1.5(3) . . . . ? N2A C4A C5A C6A 176.8(2) . . . . ? C3A C4A C5A C6A -1.3(4) . . . . ? C4A C5A C6A C7A 0.3(4) . . . . ? C5A C6A C7A C8A 0.4(4) . . . . ? C6A C7A C8A C3A -0.2(4) . . . . ? N1A C3A C8A C7A -179.5(2) . . . . ? C4A C3A C8A C7A -0.8(3) . . . . ? O2 Al1A O1 C10 137.0(3) . . . . ? O4 Al1A O1 C10 -102.3(3) . . . . ? O3 Al1A O1 C10 15.2(3) . . . . ? O1 Al1A O2 C14 -26.9(4) . . . . ? O4 Al1A O2 C14 -150.4(4) . . . . ? O3 Al1A O2 C14 91.3(4) . . . . ? O2 Al1A O3 C22 80.9(3) . . . . ? O1 Al1A O3 C22 -159.2(3) . . . . ? O4 Al1A O3 C22 -37.9(3) . . . . ? O2 Al1A O4 C18 59.6(3) . . . . ? O1 Al1A O4 C18 -61.8(3) . . . . ? O3 Al1A O4 C18 -178.9(3) . . . . ? Al1A O1 C10 C13 -49.1(4) . . . . ? Al1A O1 C10 C12 72.5(4) . . . . ? Al1A O1 C10 C11 -168.7(2) . . . . ? O1 C10 C11 F1 -42.5(3) . . . . ? C13 C10 C11 F1 -163.89(19) . . . . ? C12 C10 C11 F1 77.0(2) . . . . ? O1 C10 C11 F3 76.8(2) . . . . ? C13 C10 C11 F3 -44.6(3) . . . . ? C12 C10 C11 F3 -163.64(19) . . . . ? O1 C10 C11 F2 -162.79(19) . . . . ? C13 C10 C11 F2 75.8(2) . . . . ? C12 C10 C11 F2 -43.2(3) . . . . ? O1 C10 C12 F4 -44.7(3) . . . . ? C13 C10 C12 F4 78.7(2) . . . . ? C11 C10 C12 F4 -161.8(2) . . . . ? O1 C10 C12 F6 -166.01(19) . . . . ? C13 C10 C12 F6 -42.6(3) . . . . ? C11 C10 C12 F6 76.8(2) . . . . ? O1 C10 C12 F5 73.6(2) . . . . ? C13 C10 C12 F5 -162.92(19) . . . . ? C11 C10 C12 F5 -43.5(2) . . . . ? O1 C10 C13 F8 -37.1(3) . . . . ? C12 C10 C13 F8 -159.67(18) . . . . ? C11 C10 C13 F8 80.9(2) . . . . ? O1 C10 C13 F9 82.6(2) . . . . ? C12 C10 C13 F9 -39.9(3) . . . . ? C11 C10 C13 F9 -159.32(19) . . . . ? O1 C10 C13 F7 -156.9(2) . . . . ? C12 C10 C13 F7 80.6(2) . . . . ? C11 C10 C13 F7 -38.8(3) . . . . ? Al1A O2 C14 C16 -43.1(5) . . . . ? Al1A O2 C14 C15 78.4(4) . . . . ? Al1A O2 C14 C17 -162.6(3) . . . . ? O2 C14 C15 F10 71.1(2) . . . . ? C16 C14 C15 F10 -166.1(2) . . . . ? C17 C14 C15 F10 -46.5(3) . . . . ? O2 C14 C15 F11 -48.0(3) . . . . ? C16 C14 C15 F11 74.9(2) . . . . ? C17 C14 C15 F11 -165.52(19) . . . . ? O2 C14 C15 F12 -168.17(18) . . . . ? C16 C14 C15 F12 -45.3(3) . . . . ? C17 C14 C15 F12 74.3(2) . . . . ? O2 C14 C16 F15 -160.3(2) . . . . ? C15 C14 C16 F15 78.0(3) . . . . ? C17 C14 C16 F15 -41.9(3) . . . . ? O2 C14 C16 F14 -39.2(3) . . . . ? C15 C14 C16 F14 -160.8(2) . . . . ? C17 C14 C16 F14 79.3(2) . . . . ? O2 C14 C16 F13 78.5(3) . . . . ? C15 C14 C16 F13 -43.1(3) . . . . ? C17 C14 C16 F13 -163.0(2) . . . . ? O2 C14 C17 F18 -44.6(2) . . . . ? C16 C14 C17 F18 -165.71(19) . . . . ? C15 C14 C17 F18 74.5(2) . . . . ? O2 C14 C17 F17 -166.1(2) . . . . ? C16 C14 C17 F17 72.8(3) . . . . ? C15 C14 C17 F17 -47.0(3) . . . . ? O2 C14 C17 F16 73.9(2) . . . . ? C16 C14 C17 F16 -47.3(2) . . . . ? C15 C14 C17 F16 -167.09(19) . . . . ? Al1A O4 C18 C21 33.0(4) . . . . ? Al1A O4 C18 C20 152.5(2) . . . . ? Al1A O4 C18 C19 -88.3(3) . . . . ? O4 C18 C19 F19 79.3(2) . . . . ? C21 C18 C19 F19 -43.6(3) . . . . ? C20 C18 C19 F19 -162.6(2) . . . . ? O4 C18 C19 F20 -40.0(3) . . . . ? C21 C18 C19 F20 -162.89(19) . . . . ? C20 C18 C19 F20 78.1(2) . . . . ? O4 C18 C19 F21 -160.00(19) . . . . ? C21 C18 C19 F21 77.1(2) . . . . ? C20 C18 C19 F21 -41.9(3) . . . . ? O4 C18 C20 F24 -41.9(3) . . . . ? C21 C18 C20 F24 79.1(2) . . . . ? C19 C18 C20 F24 -161.9(2) . . . . ? O4 C18 C20 F23 -162.43(19) . . . . ? C21 C18 C20 F23 -41.3(3) . . . . ? C19 C18 C20 F23 77.7(3) . . . . ? O4 C18 C20 F22 76.7(2) . . . . ? C21 C18 C20 F22 -162.20(18) . . . . ? C19 C18 C20 F22 -43.2(3) . . . . ? O4 C18 C21 F27 -45.2(3) . . . . ? C20 C18 C21 F27 -163.79(19) . . . . ? C19 C18 C21 F27 76.9(2) . . . . ? O4 C18 C21 F25 -166.49(19) . . . . ? C20 C18 C21 F25 75.0(2) . . . . ? C19 C18 C21 F25 -44.3(3) . . . . ? O4 C18 C21 F26 73.0(2) . . . . ? C20 C18 C21 F26 -45.5(2) . . . . ? C19 C18 C21 F26 -164.80(19) . . . . ? Al1A O3 C22 C23 -58.4(3) . . . . ? Al1A O3 C22 C25 -178.2(2) . . . . ? Al1A O3 C22 C24 62.4(3) . . . . ? O3 C22 C23 F30 47.3(2) . . . . ? C25 C22 C23 F30 165.98(18) . . . . ? C24 C22 C23 F30 -74.5(2) . . . . ? O3 C22 C23 F28 -71.4(2) . . . . ? C25 C22 C23 F28 47.2(2) . . . . ? C24 C22 C23 F28 166.75(19) . . . . ? O3 C22 C23 F29 168.27(18) . . . . ? C25 C22 C23 F29 -73.1(2) . . . . ? C24 C22 C23 F29 46.5(3) . . . . ? O3 C22 C24 F33 38.4(3) . . . . ? C23 C22 C24 F33 159.89(18) . . . . ? C25 C22 C24 F33 -80.3(2) . . . . ? O3 C22 C24 F32 -81.3(2) . . . . ? C23 C22 C24 F32 40.2(3) . . . . ? C25 C22 C24 F32 160.05(18) . . . . ? O3 C22 C24 F31 158.27(18) . . . . ? C23 C22 C24 F31 -80.2(2) . . . . ? C25 C22 C24 F31 39.6(3) . . . . ? O3 C22 C25 F36 -74.9(2) . . . . ? C23 C22 C25 F36 164.97(17) . . . . ? C24 C22 C25 F36 45.6(2) . . . . ? O3 C22 C25 F34 44.2(3) . . . . ? C23 C22 C25 F34 -76.0(2) . . . . ? C24 C22 C25 F34 164.63(19) . . . . ? O3 C22 C25 F35 163.61(19) . . . . ? C23 C22 C25 F35 43.4(3) . . . . ? C24 C22 C25 F35 -75.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.785 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.517 _refine_diff_density_min -0.371 _refine_diff_density_rms 0.075 _database_code_depnum_ccdc_archive 'CCDC 945387'