Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Prof A Cowley' _publ_contact_author_address ; Department of Chemistry University of Texas at Austin AUSTIN Texas 78712 USA ; _publ_contact_author_email COWLEY@MAIL.UTEXAS.EDU _publ_section_title ; Fluoroaryl-substituted aminoalane dimers: syntheses and structures ; loop_ _publ_author_name 'A. Cowley' 'John Gordon' 'Jamie N. Jones' 'Brian L. Scott' 'Piyush Shukla' data_ccd516m _database_code_depnum_CCDC_archive 'CCDC 184628' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H20 Al2 F4 N2' _chemical_formula_weight 370.30 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' 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 _symmetry_space_group_name_H-M 'C 2/c' 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 14.241(5) _cell_length_b 7.324(2) _cell_length_c 18.512(7) _cell_angle_alpha 90.00 _cell_angle_beta 106.367(6) _cell_angle_gamma 90.00 _cell_volume 1852.7(11) _cell_formula_units_Z 4 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used 738 _cell_measurement_theta_min 4.6 _cell_measurement_theta_max 54.1 _exptl_crystal_description 'rectangular block' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.328 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.194 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9476 _exptl_absorpt_correction_T_max 0.9846 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 203(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 P4 with SMART 1k CCD' _diffrn_measurement_method '\ f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% '< 2' _diffrn_reflns_number 4813 _diffrn_reflns_av_R_equivalents 0.0414 _diffrn_reflns_av_sigmaI/netI 0.0392 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 25.35 _reflns_number_total 1698 _reflns_number_gt 1387 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens SMART (v. 4.202, Siemens 1996)' _computing_cell_refinement 'Bruker SAINT (v. 5.00, Bruker 1998)' _computing_data_reduction 'Bruker SAINT (v. 5.00, Bruker 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker AXS SHEXTL (v. 5.10)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0463P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1698 _refine_ls_number_parameters 139 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0780 _refine_ls_R_factor_gt 0.0596 _refine_ls_wR_factor_ref 0.1129 _refine_ls_wR_factor_gt 0.1086 _refine_ls_goodness_of_fit_ref 1.395 _refine_ls_restrained_S_all 1.395 _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 Al1 Al 1.09929(5) 1.07130(10) 0.29543(4) 0.0327(2) Uani 1 1 d . . . F1 F 0.94512(12) 0.44664(19) 0.39203(9) 0.0525(5) Uani 1 1 d . . . F2 F 0.83386(14) 0.9194(2) 0.51492(10) 0.0647(5) Uani 1 1 d . . . N1 N 0.96978(15) 1.0618(3) 0.31407(11) 0.0319(5) Uani 1 1 d . . . HN1 H 0.962(3) 1.157(5) 0.3300(19) 0.080 Uiso 1 1 d . . . C1 C 1.1840(2) 0.8635(4) 0.33032(17) 0.0452(7) Uani 1 1 d . . . HC1A H 1.242(3) 0.881(5) 0.3205(18) 0.080 Uiso 1 1 d . . . HC1B H 1.164(2) 0.744(5) 0.3084(18) 0.080 Uiso 1 1 d . . . HC1C H 1.196(2) 0.851(5) 0.3811(19) 0.080 Uiso 1 1 d . . . C2 C 1.1427(2) 1.3221(4) 0.31468(18) 0.0455(7) Uani 1 1 d . . . HC2A H 1.200(3) 1.347(5) 0.3024(18) 0.080 Uiso 1 1 d . . . HC2B H 1.102(3) 1.399(5) 0.289(2) 0.080 Uiso 1 1 d . . . HC2C H 1.156(3) 1.362(5) 0.3654(19) 0.080 Uiso 1 1 d . . . C3 C 0.94277(16) 0.9324(3) 0.36215(12) 0.0302(6) Uani 1 1 d . . . C4 C 0.95812(18) 0.7475(4) 0.35403(13) 0.0357(6) Uani 1 1 d . . . HC4 H 0.987(2) 0.708(5) 0.3176(19) 0.080 Uiso 1 1 d . . . C5 C 0.93022(18) 0.6272(3) 0.40064(14) 0.0362(6) Uani 1 1 d . . . C6 C 0.88872(19) 0.6776(4) 0.45552(14) 0.0398(7) Uani 1 1 d . . . HC6 H 0.872(2) 0.595(5) 0.4854(19) 0.080 Uiso 1 1 d . . . C7 C 0.87486(19) 0.8606(4) 0.46148(13) 0.0406(6) Uani 1 1 d . . . C8 C 0.90023(19) 0.9897(4) 0.41697(13) 0.0351(6) Uani 1 1 d . . . HC8 H 0.893(3) 1.107(5) 0.4252(18) 0.080 Uiso 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 Al1 0.0359(4) 0.0292(4) 0.0355(4) -0.0032(3) 0.0142(3) -0.0031(3) F1 0.0687(11) 0.0297(8) 0.0634(10) 0.0068(7) 0.0260(9) 0.0023(8) F2 0.0924(14) 0.0624(12) 0.0602(11) -0.0079(8) 0.0556(10) -0.0099(10) N1 0.0413(12) 0.0236(11) 0.0346(11) 0.0008(9) 0.0170(9) 0.0001(10) C1 0.0453(17) 0.0429(17) 0.0475(16) -0.0032(14) 0.0132(14) 0.0028(14) C2 0.0509(19) 0.0391(17) 0.0488(17) -0.0054(13) 0.0176(14) -0.0085(14) C3 0.0279(12) 0.0342(14) 0.0296(12) 0.0007(10) 0.0097(10) -0.0011(11) C4 0.0394(15) 0.0328(14) 0.0374(14) 0.0002(11) 0.0149(11) 0.0012(12) C5 0.0372(14) 0.0273(13) 0.0423(14) 0.0024(11) 0.0083(12) 0.0005(11) C6 0.0413(15) 0.0444(17) 0.0350(14) 0.0069(12) 0.0128(12) -0.0091(13) C7 0.0434(15) 0.0507(17) 0.0328(13) -0.0053(12) 0.0189(12) -0.0079(13) C8 0.0398(15) 0.0327(14) 0.0348(13) -0.0044(11) 0.0137(11) -0.0027(12) _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 Al1 C1 1.937(3) . ? Al1 C2 1.939(3) . ? Al1 N1 1.971(2) . ? Al1 N1 1.989(2) 2_755 ? Al1 Al1 2.8540(17) 2_755 ? F1 C5 1.356(3) . ? F2 C7 1.353(3) . ? N1 C3 1.425(3) . ? N1 Al1 1.989(2) 2_755 ? C3 C8 1.386(3) . ? C3 C4 1.386(3) . ? C4 C5 1.369(3) . ? C5 C6 1.363(4) . ? C6 C7 1.364(4) . ? C7 C8 1.368(4) . ? 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 C1 Al1 C2 123.12(16) . . ? C1 Al1 N1 116.10(12) . . ? C2 Al1 N1 105.50(11) . . ? C1 Al1 N1 113.28(11) . 2_755 ? C2 Al1 N1 105.13(12) . 2_755 ? N1 Al1 N1 87.64(9) . 2_755 ? C1 Al1 Al1 128.13(10) . 2_755 ? C2 Al1 Al1 108.68(10) . 2_755 ? N1 Al1 Al1 44.15(7) . 2_755 ? N1 Al1 Al1 43.63(6) 2_755 2_755 ? C3 N1 Al1 124.28(16) . . ? C3 N1 Al1 121.10(15) . 2_755 ? Al1 N1 Al1 92.22(9) . 2_755 ? C8 C3 C4 119.4(2) . . ? C8 C3 N1 120.4(2) . . ? C4 C3 N1 120.2(2) . . ? C5 C4 C3 118.6(2) . . ? F1 C5 C6 117.9(2) . . ? F1 C5 C4 118.1(2) . . ? C6 C5 C4 124.0(3) . . ? C5 C6 C7 115.5(2) . . ? F2 C7 C6 118.3(2) . . ? F2 C7 C8 117.5(2) . . ? C6 C7 C8 124.2(2) . . ? C7 C8 C3 118.4(2) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.309 _refine_diff_density_min -0.204 _refine_diff_density_rms 0.049 data_pbca2 _database_code_depnum_ccdc_archive 'CCDC 256567' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H10 Al F N' _chemical_formula_weight 166.15 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' 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 orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 12.303(3) _cell_length_b 7.3293(15) _cell_length_c 19.242(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1735.2(6) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used all _cell_measurement_theta_min 3.40 _cell_measurement_theta_max 27.58 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.272 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 0.184 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min none _exptl_absorpt_correction_T_max none _exptl_absorpt_process_details ? _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 'Nonius KAPPA-CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10786 _diffrn_reflns_av_R_equivalents 0.3007 _diffrn_reflns_av_sigmaI/netI 0.1963 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.40 _diffrn_reflns_theta_max 27.58 _reflns_number_total 2005 _reflns_number_gt 868 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect software, Nonius B.V. 1998' _computing_cell_refinement Denzo-SMN _computing_data_reduction Scalepack _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXP-97 (Sheldrick, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1071P)^2^+10.8501P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.011(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2005 _refine_ls_number_parameters 103 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2723 _refine_ls_R_factor_gt 0.1373 _refine_ls_wR_factor_ref 0.3382 _refine_ls_wR_factor_gt 0.2669 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _refine_ls_shift/su_max 0.004 _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 C1 C -0.0204(6) 0.1732(11) 0.6199(4) 0.0294(18) Uani 1 1 d . . . C2 C -0.1286(7) 0.1429(11) 0.6349(4) 0.035(2) Uani 1 1 d . . . H2 H -0.1709 0.0755 0.6042 0.042 Uiso 1 1 calc R . . C3 C -0.1755(7) 0.2115(11) 0.6954(4) 0.038(2) Uani 1 1 d . . . H3 H -0.2481 0.1896 0.7061 0.045 Uiso 1 1 calc R . . C4 C -0.1107(7) 0.3125(11) 0.7387(4) 0.037(2) Uani 1 1 d . . . C5 C -0.0042(8) 0.3462(12) 0.7253(4) 0.043(2) Uani 1 1 d . . . H5 H 0.0371 0.4163 0.7556 0.051 Uiso 1 1 calc R . . C6 C 0.0416(7) 0.2746(10) 0.6658(4) 0.0333(19) Uani 1 1 d . . . H6 H 0.1148 0.2948 0.6565 0.040 Uiso 1 1 calc R . . C7 C -0.1822(6) 0.2482(12) 0.4641(4) 0.0364(19) Uani 1 1 d . . . H7A H -0.1911 0.3370 0.5003 0.055 Uiso 1 1 calc R . . H7B H -0.2304 0.1473 0.4722 0.055 Uiso 1 1 calc R . . H7C H -0.1989 0.3029 0.4200 0.055 Uiso 1 1 calc R . . C8 C 0.0740(7) 0.3050(11) 0.4131(5) 0.043(2) Uani 1 1 d . . . H8A H 0.0802 0.4233 0.4341 0.065 Uiso 1 1 calc R . . H8B H 0.0512 0.3182 0.3656 0.065 Uiso 1 1 calc R . . H8C H 0.1432 0.2446 0.4145 0.065 Uiso 1 1 calc R . . N1 N 0.0273(5) 0.1021(8) 0.5571(3) 0.0300(16) Uani 1 1 d . . . F4 F -0.1579(5) 0.3802(7) 0.7980(3) 0.0572(16) Uani 1 1 d . . . Al1 Al -0.03235(19) 0.1615(3) 0.46348(12) 0.0313(7) 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 C1 0.032(5) 0.029(4) 0.027(4) -0.004(3) 0.005(3) 0.006(4) C2 0.032(5) 0.034(5) 0.038(5) 0.003(4) -0.004(4) 0.000(4) C3 0.024(4) 0.042(5) 0.048(6) 0.000(4) 0.007(4) 0.002(4) C4 0.041(5) 0.042(5) 0.029(5) -0.016(4) 0.004(4) 0.006(4) C5 0.048(6) 0.035(5) 0.044(5) -0.005(4) -0.004(4) 0.000(4) C6 0.043(5) 0.028(4) 0.028(4) -0.002(3) -0.006(4) -0.003(4) C7 0.029(5) 0.034(4) 0.046(5) -0.007(4) 0.000(4) 0.002(4) C8 0.045(5) 0.036(5) 0.048(6) -0.004(4) 0.000(4) -0.008(4) N1 0.026(4) 0.030(3) 0.034(4) 0.002(3) 0.003(3) 0.003(3) F4 0.068(4) 0.056(4) 0.048(3) -0.009(3) 0.012(3) 0.004(3) Al1 0.0260(13) 0.0330(13) 0.0350(14) 0.0021(11) -0.0010(11) 0.0020(10) _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 C2 1.380(11) . ? C1 C6 1.383(10) . ? C1 N1 1.441(9) . ? C2 C3 1.394(11) . ? C3 C4 1.369(11) . ? C4 C5 1.358(12) . ? C4 F4 1.373(9) . ? C5 C6 1.379(11) . ? C7 Al1 1.950(7) . ? C8 Al1 1.939(9) . ? N1 Al1 1.973(7) 5_556 ? N1 Al1 1.993(6) . ? Al1 N1 1.973(7) 5_556 ? Al1 Al1 2.866(5) 5_556 ? 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 C1 C6 119.0(7) . . ? C2 C1 N1 120.6(7) . . ? C6 C1 N1 120.4(7) . . ? C1 C2 C3 121.1(8) . . ? C4 C3 C2 117.5(7) . . ? C5 C4 C3 123.0(7) . . ? C5 C4 F4 120.0(7) . . ? C3 C4 F4 117.0(8) . . ? C4 C5 C6 118.9(8) . . ? C5 C6 C1 120.6(8) . . ? C1 N1 Al1 122.4(5) . 5_556 ? C1 N1 Al1 122.0(5) . . ? Al1 N1 Al1 92.5(3) 5_556 . ? C8 Al1 C7 117.6(4) . . ? C8 Al1 N1 114.2(3) . 5_556 ? C7 Al1 N1 110.5(3) . 5_556 ? C8 Al1 N1 108.8(3) . . ? C7 Al1 N1 114.4(3) . . ? N1 Al1 N1 87.5(3) 5_556 . ? C8 Al1 Al1 120.4(3) . 5_556 ? C7 Al1 Al1 121.9(3) . 5_556 ? N1 Al1 Al1 44.02(19) 5_556 5_556 ? N1 Al1 Al1 43.46(19) . 5_556 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.58 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.675 _refine_diff_density_min -0.752 _refine_diff_density_rms 0.142 data_ccd518s _database_code_depnum_ccdc_archive 'CCDC 256568' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H16 Al2 F8 N2' _chemical_formula_weight 442.27 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' N N 0.0061 0.0033 '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 triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.712(3) _cell_length_b 9.689(4) _cell_length_c 17.153(8) _cell_angle_alpha 91.044(7) _cell_angle_beta 92.103(8) _cell_angle_gamma 94.798(9) _cell_volume 1276.1(10) _cell_formula_units_Z 2 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used 825 _cell_measurement_theta_min 4.8 _cell_measurement_theta_max 54.5 _exptl_crystal_description irregular _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.151 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.173 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9532 _exptl_absorpt_correction_T_max 0.9795 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 203(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 P4 with SMART 1k CCD' _diffrn_measurement_method '\f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% '< 2' _diffrn_reflns_number 6287 _diffrn_reflns_av_R_equivalents 0.0489 _diffrn_reflns_av_sigmaI/netI 0.0592 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.19 _diffrn_reflns_theta_max 22.46 _reflns_number_total 3101 _reflns_number_gt 2331 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens SMART (v. 4.202, Siemens 1996)' _computing_cell_refinement 'Bruker SAINT (v. 5.00, Bruker 1998)' _computing_data_reduction 'Bruker SAINT (v. 5.00, Bruker 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker AXS SHEXTL (v. 5.10)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0849P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3101 _refine_ls_number_parameters 259 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1070 _refine_ls_R_factor_gt 0.0822 _refine_ls_wR_factor_ref 0.2091 _refine_ls_wR_factor_gt 0.2025 _refine_ls_goodness_of_fit_ref 1.537 _refine_ls_restrained_S_all 1.537 _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 Al1 Al 0.4319(2) 0.39297(17) 0.14146(10) 0.0324(5) Uani 1 1 d . . . Al2 Al 0.4638(2) 0.55509(17) 0.28576(10) 0.0313(5) Uani 1 1 d . . . F1 F 0.0874(4) 0.5375(3) 0.19850(19) 0.0419(9) Uani 1 1 d . . . F2 F -0.1574(5) 0.6954(4) 0.1412(2) 0.0552(11) Uani 1 1 d . . . F3 F 0.2732(5) 0.9756(3) 0.0174(2) 0.0531(11) Uani 1 1 d . . . F4 F 0.5206(5) 0.8211(3) 0.0771(2) 0.0464(10) Uani 1 1 d . . . F5 F 0.4874(5) 0.3631(3) 0.41376(19) 0.0510(11) Uani 1 1 d . . . F6 F 0.6169(6) 0.1451(4) 0.4841(2) 0.0632(12) Uani 1 1 d . . . F7 F 0.5643(5) -0.1062(3) 0.2462(2) 0.0561(11) Uani 1 1 d . . . F8 F 0.4297(5) 0.1082(3) 0.17626(18) 0.0450(10) Uani 1 1 d . . . N1 N 0.4400(7) 0.5950(5) 0.1710(3) 0.0305(12) Uani 1 1 d . . . H1 H 0.538(11) 0.631(8) 0.157(4) 0.080 Uiso 1 1 d . . . H2 H 0.259(10) 0.316(7) 0.259(4) 0.080 Uiso 1 1 d . . . N2 N 0.3907(7) 0.3592(4) 0.2541(3) 0.0302(12) Uani 1 1 d . . . C1 C 0.6657(9) 0.3591(7) 0.1145(4) 0.0493(18) Uani 1 1 d . . . H1A H 0.7459 0.3932 0.1559 0.074 Uiso 1 1 calc R . . H1B H 0.6943 0.4059 0.0673 0.074 Uiso 1 1 calc R . . H1C H 0.6730 0.2614 0.1070 0.074 Uiso 1 1 calc R . . C2 C 0.2328(9) 0.3361(7) 0.0715(4) 0.0511(19) Uani 1 1 d . . . H2A H 0.1280 0.3609 0.0946 0.077 Uiso 1 1 calc R . . H2B H 0.2263 0.2376 0.0629 0.077 Uiso 1 1 calc R . . H2C H 0.2463 0.3817 0.0226 0.077 Uiso 1 1 calc R . . C3 C 0.7121(8) 0.5814(6) 0.3136(4) 0.0423(16) Uani 1 1 d . . . H3A H 0.7757 0.5319 0.2767 0.063 Uiso 1 1 calc R . . H3B H 0.7328 0.5468 0.3649 0.063 Uiso 1 1 calc R . . H3C H 0.7501 0.6782 0.3129 0.063 Uiso 1 1 calc R . . C4 C 0.2946(10) 0.6451(6) 0.3488(4) 0.0516(19) Uani 1 1 d . . . H4A H 0.1792 0.6221 0.3269 0.077 Uiso 1 1 calc R . . H4B H 0.3207 0.7437 0.3487 0.077 Uiso 1 1 calc R . . H4C H 0.3016 0.6132 0.4014 0.077 Uiso 1 1 calc R . . C5 C 0.3116(8) 0.6767(5) 0.1411(3) 0.0278(14) Uani 1 1 d . . . C6 C 0.1366(8) 0.6489(6) 0.1547(3) 0.0325(15) Uani 1 1 d . . . C7 C 0.0102(8) 0.7280(6) 0.1247(3) 0.0351(15) Uani 1 1 d . . . C8 C 0.0519(8) 0.8401(6) 0.0792(3) 0.0373(16) Uani 1 1 d . . . H8 H -0.0329 0.8943 0.0596 0.045 Uiso 1 1 calc R . . C9 C 0.2241(9) 0.8685(6) 0.0642(3) 0.0389(17) Uani 1 1 d . . . C10 C 0.3543(7) 0.7902(5) 0.0943(3) 0.0269(14) Uani 1 1 d . . . C11 C 0.4622(8) 0.2442(5) 0.2918(3) 0.0298(14) Uani 1 1 d . . . C12 C 0.5085(8) 0.2485(6) 0.3713(3) 0.0345(15) Uani 1 1 d . . . C13 C 0.5728(8) 0.1354(6) 0.4070(3) 0.0375(16) Uani 1 1 d . . . C14 C 0.5943(8) 0.0147(6) 0.3665(3) 0.0386(16) Uani 1 1 d . . . H14 H 0.6386 -0.0607 0.3907 0.046 Uiso 1 1 calc R . . C15 C 0.5474(8) 0.0112(6) 0.2893(4) 0.0390(16) Uani 1 1 d . . . C16 C 0.4821(8) 0.1206(6) 0.2522(3) 0.0284(14) 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 Al1 0.0375(12) 0.0314(10) 0.0278(10) 0.0021(7) -0.0019(8) 0.0020(8) Al2 0.0350(12) 0.0310(10) 0.0276(10) 0.0010(7) -0.0019(8) 0.0024(8) F1 0.031(2) 0.043(2) 0.052(2) 0.0191(17) 0.0026(16) -0.0022(16) F2 0.027(3) 0.072(3) 0.068(3) 0.020(2) 0.0014(18) 0.0024(18) F3 0.051(3) 0.046(2) 0.064(3) 0.0318(19) 0.005(2) 0.0051(18) F4 0.038(3) 0.046(2) 0.055(2) 0.0170(17) 0.0062(18) -0.0051(17) F5 0.080(3) 0.041(2) 0.033(2) -0.0046(16) 0.0045(19) 0.0065(19) F6 0.096(4) 0.058(2) 0.035(2) 0.0093(18) -0.019(2) 0.008(2) F7 0.083(3) 0.030(2) 0.056(2) -0.0015(18) -0.004(2) 0.0086(19) F8 0.066(3) 0.038(2) 0.030(2) -0.0007(15) -0.0086(18) -0.0006(17) N1 0.028(3) 0.029(3) 0.034(3) 0.007(2) -0.004(2) -0.003(2) N2 0.035(3) 0.027(3) 0.028(3) 0.007(2) -0.002(2) -0.001(2) C1 0.062(5) 0.045(4) 0.040(4) -0.002(3) 0.010(3) -0.003(3) C2 0.061(5) 0.053(4) 0.037(4) -0.003(3) -0.017(3) -0.001(4) C3 0.039(4) 0.048(4) 0.039(4) 0.003(3) -0.009(3) 0.003(3) C4 0.065(5) 0.044(4) 0.046(4) -0.007(3) 0.017(4) 0.003(4) C5 0.028(4) 0.029(3) 0.025(3) -0.004(3) -0.009(3) 0.001(3) C6 0.029(4) 0.030(3) 0.038(4) 0.005(3) 0.000(3) 0.000(3) C7 0.024(4) 0.047(4) 0.034(4) 0.001(3) -0.002(3) -0.003(3) C8 0.036(5) 0.039(4) 0.038(4) 0.005(3) -0.009(3) 0.013(3) C9 0.050(5) 0.037(4) 0.028(3) 0.005(3) -0.001(3) -0.005(3) C10 0.017(4) 0.031(3) 0.033(3) 0.008(3) 0.005(3) 0.002(3) C11 0.029(4) 0.030(3) 0.029(3) 0.007(3) 0.000(3) -0.005(3) C12 0.036(4) 0.031(3) 0.036(4) 0.006(3) 0.002(3) -0.005(3) C13 0.041(4) 0.042(4) 0.028(4) 0.014(3) -0.006(3) -0.006(3) C14 0.038(4) 0.035(4) 0.043(4) 0.014(3) -0.007(3) 0.003(3) C15 0.035(4) 0.032(4) 0.049(4) 0.003(3) -0.001(3) -0.006(3) C16 0.025(4) 0.032(3) 0.028(3) 0.004(3) -0.001(3) -0.003(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 Al1 C1 1.931(7) . ? Al1 C2 1.949(6) . ? Al1 N2 1.998(5) . ? Al1 N1 2.008(5) . ? Al1 Al2 2.899(2) . ? Al2 C3 1.952(6) . ? Al2 C4 1.972(6) . ? Al2 N2 1.994(5) . ? Al2 N1 2.019(5) . ? F1 C6 1.362(6) . ? F1 N2 3.152(6) . ? F2 C7 1.346(7) . ? F3 C9 1.359(6) . ? F4 C10 1.338(6) . ? F4 N1 2.784(6) . ? F5 C12 1.342(6) . ? F6 C13 1.354(7) . ? F7 C15 1.363(7) . ? F8 C16 1.350(6) . ? N1 C5 1.406(7) . ? N2 C11 1.438(7) . ? C5 C6 1.383(8) . ? C5 C10 1.397(7) . ? C6 C7 1.380(8) . ? C7 C8 1.373(8) . ? C8 C9 1.369(9) . ? C9 C10 1.398(8) . ? C11 C16 1.388(8) . ? C11 C12 1.396(8) . ? C12 C13 1.383(8) . ? C13 C14 1.374(8) . ? C14 C15 1.360(8) . ? C15 C16 1.368(8) . ? 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 C1 Al1 C2 121.2(3) . . ? C1 Al1 N2 111.9(3) . . ? C2 Al1 N2 114.3(3) . . ? C1 Al1 N1 106.0(3) . . ? C2 Al1 N1 111.7(3) . . ? N2 Al1 N1 85.61(19) . . ? C1 Al1 Al2 106.4(2) . . ? C2 Al1 Al2 132.1(2) . . ? N2 Al1 Al2 43.37(13) . . ? N1 Al1 Al2 44.10(14) . . ? C3 Al2 C4 120.2(3) . . ? C3 Al2 N2 111.7(3) . . ? C4 Al2 N2 114.5(3) . . ? C3 Al2 N1 106.3(2) . . ? C4 Al2 N1 113.1(3) . . ? N2 Al2 N1 85.45(19) . . ? C3 Al2 Al1 106.4(2) . . ? C4 Al2 Al1 133.2(2) . . ? N2 Al2 Al1 43.48(13) . . ? N1 Al2 Al1 43.82(14) . . ? C6 F1 N2 115.4(3) . . ? C10 F4 N1 61.4(3) . . ? C5 N1 Al1 120.1(3) . . ? C5 N1 Al2 121.8(4) . . ? Al1 N1 Al2 92.1(2) . . ? C5 N1 F4 57.9(3) . . ? Al1 N1 F4 127.8(2) . . ? Al2 N1 F4 136.0(2) . . ? C11 N2 Al2 122.1(4) . . ? C11 N2 Al1 120.0(4) . . ? Al2 N2 Al1 93.16(19) . . ? C11 N2 F1 154.6(4) . . ? Al2 N2 F1 73.24(16) . . ? Al1 N2 F1 75.34(16) . . ? C6 C5 C10 116.0(5) . . ? C6 C5 N1 122.6(5) . . ? C10 C5 N1 121.4(5) . . ? F1 C6 C7 118.9(5) . . ? F1 C6 C5 118.4(5) . . ? C7 C6 C5 122.7(5) . . ? F2 C7 C8 119.3(6) . . ? F2 C7 C6 119.3(5) . . ? C8 C7 C6 121.4(6) . . ? C9 C8 C7 116.9(6) . . ? F3 C9 C8 119.7(6) . . ? F3 C9 C10 117.7(5) . . ? C8 C9 C10 122.6(5) . . ? F4 C10 C5 119.3(5) . . ? F4 C10 C9 120.3(5) . . ? C5 C10 C9 120.4(5) . . ? C16 C11 C12 116.1(5) . . ? C16 C11 N2 122.1(5) . . ? C12 C11 N2 121.7(5) . . ? F5 C12 C13 119.7(5) . . ? F5 C12 C11 119.4(5) . . ? C13 C12 C11 120.9(5) . . ? F6 C13 C14 119.3(5) . . ? F6 C13 C12 118.6(5) . . ? C14 C13 C12 122.1(5) . . ? C15 C14 C13 116.5(6) . . ? F7 C15 C14 119.2(6) . . ? F7 C15 C16 117.9(5) . . ? C14 C15 C16 122.9(6) . . ? F8 C16 C15 120.0(5) . . ? F8 C16 C11 118.5(5) . . ? C15 C16 C11 121.4(5) . . ? _diffrn_measured_fraction_theta_max 0.934 _diffrn_reflns_theta_full 22.46 _diffrn_measured_fraction_theta_full 0.934 _refine_diff_density_max 0.344 _refine_diff_density_min -0.372 _refine_diff_density_rms 0.083 data_ccd522 _database_code_depnum_ccdc_archive 'CCDC 256569' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H22 Al2 F2 N2' _chemical_formula_weight 334.32 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' 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 _symmetry_space_group_name_H-M 'P 21/n' 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 10.262(2) _cell_length_b 14.141(3) _cell_length_c 13.064(3) _cell_angle_alpha 90.00 _cell_angle_beta 110.505(4) _cell_angle_gamma 90.00 _cell_volume 1775.5(7) _cell_formula_units_Z 4 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used 969 _cell_measurement_theta_min 5.1 _cell_measurement_theta_max 54.9 _exptl_crystal_description irregular _exptl_crystal_colour colorless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.251 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.180 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 203(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 P4 with SMART 1k CCD' _diffrn_measurement_method '\f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% '< 2' _diffrn_reflns_number 10885 _diffrn_reflns_av_R_equivalents 0.0474 _diffrn_reflns_av_sigmaI/netI 0.0455 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 25.35 _reflns_number_total 3149 _reflns_number_gt 2476 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens SMART (v. 4.202, Siemens 1996)' _computing_cell_refinement 'Bruker SAINT (v. 5.00, Bruker 1998)' _computing_data_reduction 'Bruker SAINT (v. 5.00, Bruker 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker AXS SHEXTL (v. 5.10)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0579P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3149 _refine_ls_number_parameters 205 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0970 _refine_ls_R_factor_gt 0.0700 _refine_ls_wR_factor_ref 0.1392 _refine_ls_wR_factor_gt 0.1325 _refine_ls_goodness_of_fit_ref 1.382 _refine_ls_restrained_S_all 1.382 _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 Al1 Al 0.89148(9) 0.03484(7) 0.16583(7) 0.0302(3) Uani 1 1 d . . . Al2 Al 0.86260(9) 0.21241(7) 0.26316(7) 0.0291(3) Uani 1 1 d . . . F1 F 0.87051(18) 0.24894(14) -0.06681(13) 0.0454(5) Uani 1 1 d . . . F2 F 0.86286(17) -0.01156(13) 0.48619(13) 0.0457(5) Uani 1 1 d . . . N1 N 0.9050(2) 0.17103(18) 0.13322(19) 0.0292(6) Uani 1 1 d . . . H1 H 0.828(4) 0.183(3) 0.076(3) 0.080 Uiso 1 1 d . . . N2 N 0.8429(2) 0.07596(18) 0.29296(19) 0.0275(6) Uani 1 1 d . . . H2 H 0.909(4) 0.063(3) 0.349(3) 0.080 Uiso 1 1 d . . . C1 C 1.0728(3) -0.0263(2) 0.2178(3) 0.0496(9) Uani 1 1 d . . . H1A H 1.1361 0.0107 0.2756 0.074 Uiso 1 1 calc R . . H1B H 1.1077 -0.0313 0.1587 0.074 Uiso 1 1 calc R . . H1C H 1.0641 -0.0883 0.2446 0.074 Uiso 1 1 calc R . . C2 C 0.7366(4) -0.0201(2) 0.0482(2) 0.0449(9) Uani 1 1 d . . . H2A H 0.6561 0.0195 0.0334 0.067 Uiso 1 1 calc R . . H2B H 0.7165 -0.0819 0.0695 0.067 Uiso 1 1 calc R . . H2C H 0.7605 -0.0252 -0.0163 0.067 Uiso 1 1 calc R . . C3 C 1.0210(3) 0.2620(2) 0.3827(3) 0.0431(9) Uani 1 1 d . . . H3A H 1.0992 0.2205 0.3958 0.065 Uiso 1 1 calc R . . H3B H 0.9975 0.2663 0.4475 0.065 Uiso 1 1 calc R . . H3C H 1.0444 0.3237 0.3637 0.065 Uiso 1 1 calc R . . C4 C 0.6858(3) 0.2799(2) 0.2142(3) 0.0424(8) Uani 1 1 d . . . H4A H 0.6197 0.2459 0.1551 0.064 Uiso 1 1 calc R . . H4B H 0.6991 0.3420 0.1898 0.064 Uiso 1 1 calc R . . H4C H 0.6517 0.2851 0.2737 0.064 Uiso 1 1 calc R . . C5 C 1.0218(3) 0.2062(2) 0.1083(2) 0.0258(6) Uani 1 1 d . . . C6 C 1.0037(3) 0.2458(2) 0.0075(2) 0.0309(7) Uani 1 1 d . . . C7 C 1.1090(3) 0.2830(2) -0.0213(2) 0.0366(8) Uani 1 1 d . . . H7 H 1.0911 0.3101 -0.0898 0.044 Uiso 1 1 calc R . . C8 C 1.2422(3) 0.2791(2) 0.0538(3) 0.0399(8) Uani 1 1 d . . . H8 H 1.3161 0.3036 0.0365 0.048 Uiso 1 1 calc R . . C9 C 1.2659(3) 0.2389(2) 0.1550(3) 0.0379(8) Uani 1 1 d . . . H9 H 1.3561 0.2357 0.2053 0.045 Uiso 1 1 calc R . . C10 C 1.1572(3) 0.2036(2) 0.1823(2) 0.0333(7) Uani 1 1 d . . . H10 H 1.1748 0.1776 0.2513 0.040 Uiso 1 1 calc R . . C11 C 0.7222(3) 0.0403(2) 0.3119(2) 0.0257(6) Uani 1 1 d . . . C12 C 0.7334(3) -0.0042(2) 0.4085(2) 0.0306(7) Uani 1 1 d . . . C13 C 0.6227(3) -0.0422(2) 0.4301(2) 0.0374(8) Uani 1 1 d . . . H13 H 0.6358 -0.0721 0.4963 0.045 Uiso 1 1 calc R . . C14 C 0.4919(3) -0.0351(2) 0.3517(3) 0.0387(8) Uani 1 1 d . . . H14 H 0.4154 -0.0609 0.3642 0.046 Uiso 1 1 calc R . . C15 C 0.4752(3) 0.0106(2) 0.2546(2) 0.0364(8) Uani 1 1 d . . . H15 H 0.3868 0.0168 0.2022 0.044 Uiso 1 1 calc R . . C16 C 0.5891(3) 0.0473(2) 0.2346(2) 0.0325(7) Uani 1 1 d . . . H16 H 0.5763 0.0771 0.1683 0.039 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 Al1 0.0319(5) 0.0279(5) 0.0344(5) 0.0000(4) 0.0159(4) -0.0007(4) Al2 0.0297(5) 0.0270(5) 0.0333(5) -0.0007(4) 0.0145(4) -0.0018(4) F1 0.0396(11) 0.0623(14) 0.0302(9) 0.0086(9) 0.0069(8) 0.0020(9) F2 0.0341(10) 0.0624(14) 0.0366(10) 0.0144(9) 0.0074(8) -0.0004(9) N1 0.0268(13) 0.0344(16) 0.0280(12) 0.0033(11) 0.0116(10) 0.0000(11) N2 0.0230(13) 0.0322(15) 0.0286(12) 0.0058(11) 0.0105(10) -0.0002(11) C1 0.043(2) 0.040(2) 0.070(2) 0.0084(18) 0.0261(18) 0.0086(16) C2 0.055(2) 0.039(2) 0.0406(18) -0.0055(16) 0.0164(16) -0.0042(16) C3 0.045(2) 0.043(2) 0.0427(18) -0.0068(16) 0.0168(16) -0.0101(16) C4 0.044(2) 0.041(2) 0.0490(19) 0.0080(16) 0.0244(16) 0.0067(16) C5 0.0304(16) 0.0214(16) 0.0285(15) -0.0015(12) 0.0141(12) 0.0005(12) C6 0.0316(17) 0.0315(19) 0.0294(15) -0.0030(13) 0.0105(13) 0.0027(14) C7 0.050(2) 0.0321(19) 0.0368(17) 0.0038(14) 0.0263(16) -0.0016(15) C8 0.0388(19) 0.038(2) 0.052(2) -0.0003(16) 0.0280(16) -0.0072(15) C9 0.0255(17) 0.036(2) 0.0497(19) -0.0062(15) 0.0106(15) -0.0045(14) C10 0.0321(17) 0.0336(19) 0.0344(16) 0.0030(14) 0.0118(14) -0.0020(14) C11 0.0281(15) 0.0204(16) 0.0320(15) -0.0018(12) 0.0147(12) -0.0022(12) C12 0.0277(16) 0.034(2) 0.0296(15) 0.0021(13) 0.0088(13) 0.0036(13) C13 0.0427(19) 0.037(2) 0.0384(17) 0.0044(15) 0.0222(15) -0.0017(15) C14 0.0342(19) 0.038(2) 0.051(2) -0.0013(16) 0.0245(16) -0.0082(15) C15 0.0244(16) 0.042(2) 0.0407(18) -0.0072(15) 0.0088(13) -0.0031(14) C16 0.0320(17) 0.0374(19) 0.0293(15) -0.0009(14) 0.0121(13) -0.0010(14) _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 Al1 C2 1.945(3) . ? Al1 C1 1.946(3) . ? Al1 N2 1.981(3) . ? Al1 N1 1.988(3) . ? Al1 Al2 2.8764(14) . ? Al2 C3 1.948(3) . ? Al2 C4 1.949(3) . ? Al2 N1 1.982(3) . ? Al2 N2 1.993(3) . ? F1 C6 1.372(3) . ? F1 N1 2.742(3) . ? F2 C12 1.364(3) . ? F2 N2 2.754(3) . ? N1 C5 1.437(3) . ? N2 C11 1.436(3) . ? C5 C6 1.382(4) . ? C5 C10 1.388(4) . ? C6 C7 1.368(4) . ? C7 C8 1.377(4) . ? C8 C9 1.380(4) . ? C9 C10 1.379(4) . ? C11 C12 1.379(4) . ? C11 C16 1.388(4) . ? C12 C13 1.372(4) . ? C13 C14 1.378(4) . ? C14 C15 1.380(4) . ? C15 C16 1.385(4) . ? 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 Al1 C1 121.02(16) . . ? C2 Al1 N2 113.79(13) . . ? C1 Al1 N2 109.20(13) . . ? C2 Al1 N1 108.48(13) . . ? C1 Al1 N1 112.04(13) . . ? N2 Al1 N1 87.26(11) . . ? C2 Al1 Al2 121.06(11) . . ? C1 Al1 Al2 117.88(12) . . ? N2 Al1 Al2 43.79(8) . . ? N1 Al1 Al2 43.50(7) . . ? C3 Al2 C4 120.41(16) . . ? C3 Al2 N1 114.90(13) . . ? C4 Al2 N1 108.77(12) . . ? C3 Al2 N2 107.78(13) . . ? C4 Al2 N2 113.06(13) . . ? N1 Al2 N2 87.09(11) . . ? C3 Al2 Al1 118.84(11) . . ? C4 Al2 Al1 120.71(11) . . ? N1 Al2 Al1 43.64(8) . . ? N2 Al2 Al1 43.48(7) . . ? C6 F1 N1 63.21(15) . . ? C12 F2 N2 62.81(15) . . ? C5 N1 Al2 122.87(19) . . ? C5 N1 Al1 120.68(19) . . ? Al2 N1 Al1 92.86(11) . . ? C5 N1 F1 58.94(14) . . ? Al2 N1 F1 134.72(13) . . ? Al1 N1 F1 126.74(12) . . ? C11 N2 Al1 121.79(19) . . ? C11 N2 Al2 121.73(19) . . ? Al1 N2 Al2 92.74(11) . . ? C11 N2 F2 58.44(14) . . ? Al1 N2 F2 132.58(12) . . ? Al2 N2 F2 129.37(12) . . ? C6 C5 C10 116.2(3) . . ? C6 C5 N1 120.8(2) . . ? C10 C5 N1 123.0(2) . . ? C7 C6 F1 118.7(3) . . ? C7 C6 C5 124.3(3) . . ? F1 C6 C5 117.0(3) . . ? C6 C7 C8 118.1(3) . . ? C7 C8 C9 119.8(3) . . ? C10 C9 C8 120.7(3) . . ? C9 C10 C5 120.9(3) . . ? C12 C11 C16 116.3(3) . . ? C12 C11 N2 121.1(2) . . ? C16 C11 N2 122.5(3) . . ? F2 C12 C13 118.5(3) . . ? F2 C12 C11 117.6(3) . . ? C13 C12 C11 123.8(3) . . ? C12 C13 C14 118.7(3) . . ? C13 C14 C15 119.5(3) . . ? C14 C15 C16 120.5(3) . . ? C15 C16 C11 121.1(3) . . ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.297 _refine_diff_density_min -0.275 _refine_diff_density_rms 0.056 data_ccd525 _database_code_depnum_ccdc_archive 'CCDC 256570' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H16 Al2 F8 N2' _chemical_formula_weight 442.27 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' N N 0.0061 0.0033 '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' F F 0.0171 0.0103 '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 6.8832(18) _cell_length_b 7.288(2) _cell_length_c 10.168(3) _cell_angle_alpha 102.623(4) _cell_angle_beta 90.873(5) _cell_angle_gamma 105.897(5) _cell_volume 477.2(2) _cell_formula_units_Z 1 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used 729 _cell_measurement_theta_min 6.4 _cell_measurement_theta_max 54.6 _exptl_crystal_description irregular _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.082 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.539 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 224 _exptl_absorpt_coefficient_mu 0.231 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 203(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 P4 with SMART 1k CCD' _diffrn_measurement_method '\f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% '< 2' _diffrn_reflns_number 3066 _diffrn_reflns_av_R_equivalents 0.0126 _diffrn_reflns_av_sigmaI/netI 0.0167 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 25.34 _reflns_number_total 1605 _reflns_number_gt 1426 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens SMART (v. 4.202, Siemens 1996)' _computing_cell_refinement 'Bruker SAINT (v. 5.00, Bruker 1998)' _computing_data_reduction 'Bruker SAINT (v. 5.00, Bruker 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker AXS SHEXTL (v. 5.10)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0628P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1605 _refine_ls_number_parameters 130 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0505 _refine_ls_R_factor_gt 0.0442 _refine_ls_wR_factor_ref 0.1388 _refine_ls_wR_factor_gt 0.1368 _refine_ls_goodness_of_fit_ref 1.697 _refine_ls_restrained_S_all 1.697 _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 Al1 Al 0.47676(12) 0.18556(10) 0.57405(7) 0.0337(3) Uani 1 1 d . . . N1 N 0.4259(3) 0.0298(3) 0.38309(19) 0.0333(5) Uani 1 1 d . . . HN1 H 0.307(6) -0.008(6) 0.372(4) 0.080 Uiso 1 1 d . . . F1 F 0.1417(3) 0.0376(3) 0.19170(17) 0.0571(5) Uani 1 1 d . . . F2 F 0.2383(3) 0.1935(3) -0.02365(16) 0.0585(5) Uani 1 1 d . . . F3 F 0.6323(3) 0.3558(2) -0.06196(16) 0.0581(5) Uani 1 1 d . . . F4 F 0.9278(3) 0.3643(3) 0.12075(19) 0.0660(6) Uani 1 1 d . . . C1 C 0.7094(5) 0.4178(4) 0.6009(3) 0.0479(7) Uani 1 1 d . . . H1A H 0.8233 0.3818 0.5613 0.072 Uiso 1 1 calc R . . H1B H 0.7424 0.4734 0.6960 0.072 Uiso 1 1 calc R . . H1C H 0.6771 0.5126 0.5587 0.072 Uiso 1 1 calc R . . C2 C 0.2135(5) 0.1947(5) 0.6391(3) 0.0489(7) Uani 1 1 d . . . H2A H 0.1203 0.0655 0.6155 0.073 Uiso 1 1 calc R . . H2B H 0.1629 0.2812 0.5981 0.073 Uiso 1 1 calc R . . H2C H 0.2278 0.2421 0.7355 0.073 Uiso 1 1 calc R . . C3 C 0.4851(4) 0.1161(3) 0.2704(2) 0.0298(5) Uani 1 1 d . . . C4 C 0.3382(4) 0.1177(4) 0.1761(2) 0.0352(6) Uani 1 1 d . . . C5 C 0.3862(4) 0.1983(4) 0.0654(2) 0.0387(6) Uani 1 1 d . . . C6 C 0.5847(4) 0.2810(4) 0.0472(2) 0.0403(7) Uani 1 1 d . . . C7 C 0.7325(4) 0.2828(4) 0.1404(3) 0.0423(7) Uani 1 1 d . . . C8 C 0.6860(4) 0.2027(4) 0.2506(3) 0.0392(6) Uani 1 1 d . . . H8 H 0.7892 0.2065 0.3122 0.047 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 Al1 0.0425(5) 0.0349(4) 0.0285(4) 0.0125(3) 0.0060(3) 0.0145(3) N1 0.0372(13) 0.0372(11) 0.0294(10) 0.0154(8) 0.0033(9) 0.0110(9) F1 0.0432(11) 0.0772(12) 0.0527(10) 0.0289(9) -0.0008(8) 0.0096(9) F2 0.0639(12) 0.0784(12) 0.0407(9) 0.0261(8) -0.0079(8) 0.0234(9) F3 0.0854(14) 0.0591(10) 0.0403(9) 0.0300(8) 0.0202(9) 0.0223(9) F4 0.0508(12) 0.0817(13) 0.0703(12) 0.0406(10) 0.0192(9) 0.0078(9) C1 0.0593(19) 0.0400(14) 0.0455(15) 0.0148(12) 0.0034(14) 0.0122(13) C2 0.0569(19) 0.0621(18) 0.0405(14) 0.0233(13) 0.0138(13) 0.0285(15) C3 0.0372(15) 0.0298(11) 0.0258(11) 0.0097(9) 0.0055(10) 0.0125(10) C4 0.0372(16) 0.0359(12) 0.0332(12) 0.0108(10) 0.0029(11) 0.0092(11) C5 0.0522(18) 0.0395(13) 0.0279(12) 0.0083(10) -0.0035(11) 0.0185(12) C6 0.0598(19) 0.0371(13) 0.0316(12) 0.0165(10) 0.0129(12) 0.0189(12) C7 0.0411(17) 0.0416(14) 0.0450(14) 0.0151(12) 0.0131(12) 0.0089(12) C8 0.0418(17) 0.0437(14) 0.0355(13) 0.0136(11) 0.0024(11) 0.0142(12) _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 Al1 C2 1.952(3) . ? Al1 C1 1.950(3) . ? Al1 N1 1.992(2) 2_656 ? Al1 N1 1.995(2) . ? Al1 Al1 2.8972(15) 2_656 ? N1 C3 1.437(3) . ? N1 Al1 1.992(2) 2_656 ? F1 C4 1.345(3) . ? F2 C5 1.340(3) . ? F3 C6 1.347(3) . ? F4 C7 1.350(3) . ? C3 C8 1.391(4) . ? C3 C4 1.387(3) . ? C4 C5 1.384(3) . ? C5 C6 1.368(4) . ? C6 C7 1.375(4) . ? C7 C8 1.376(4) . ? 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 Al1 C1 122.67(13) . . ? C2 Al1 N1 114.25(10) . 2_656 ? C1 Al1 N1 107.48(11) . 2_656 ? C2 Al1 N1 107.02(12) . . ? C1 Al1 N1 112.96(11) . . ? N1 Al1 N1 86.79(9) 2_656 . ? C2 Al1 Al1 118.95(10) . 2_656 ? C1 Al1 Al1 118.37(10) . 2_656 ? N1 Al1 Al1 43.43(6) 2_656 2_656 ? N1 Al1 Al1 43.36(6) . 2_656 ? C3 N1 Al1 123.91(15) . 2_656 ? C3 N1 Al1 122.62(15) . . ? Al1 N1 Al1 93.21(8) 2_656 . ? C8 C3 C4 117.1(2) . . ? C8 C3 N1 123.2(2) . . ? C4 C3 N1 119.7(2) . . ? F1 C4 C5 118.4(2) . . ? F1 C4 C3 119.3(2) . . ? C5 C4 C3 122.3(2) . . ? F2 C5 C6 120.4(2) . . ? F2 C5 C4 119.9(2) . . ? C6 C5 C4 119.7(2) . . ? F3 C6 C5 119.8(2) . . ? F3 C6 C7 121.3(2) . . ? C5 C6 C7 118.9(2) . . ? F4 C7 C6 118.2(2) . . ? F4 C7 C8 120.0(2) . . ? C6 C7 C8 121.8(2) . . ? C7 C8 C3 120.2(2) . . ? _diffrn_measured_fraction_theta_max 0.914 _diffrn_reflns_theta_full 25.34 _diffrn_measured_fraction_theta_full 0.914 _refine_diff_density_max 0.527 _refine_diff_density_min -0.165 _refine_diff_density_rms 0.050 data_ccd515 _database_code_depnum_ccdc_archive 'CCDC 256571' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H22 Al2 F10 N2' _chemical_formula_weight 570.39 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' 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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.7217(18) _cell_length_b 9.699(2) _cell_length_c 17.933(4) _cell_angle_alpha 75.731(4) _cell_angle_beta 88.946(4) _cell_angle_gamma 82.922(4) _cell_volume 1291.6(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.467 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 580 _exptl_absorpt_coefficient_mu 0.200 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9388 _exptl_absorpt_correction_T_max 0.9462 _exptl_absorpt_process_details ? _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8310 _diffrn_reflns_av_R_equivalents 0.0190 _diffrn_reflns_av_sigmaI/netI 0.0250 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.17 _diffrn_reflns_theta_max 25.35 _reflns_number_total 4340 _reflns_number_gt 3577 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0616P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4340 _refine_ls_number_parameters 340 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0613 _refine_ls_R_factor_gt 0.0490 _refine_ls_wR_factor_ref 0.1322 _refine_ls_wR_factor_gt 0.1282 _refine_ls_goodness_of_fit_ref 1.433 _refine_ls_restrained_S_all 1.433 _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 Al1 Al 0.49851(10) 0.45011(8) 0.35007(4) 0.0333(2) Uani 1 1 d . . . Al2 Al 0.51359(10) 0.35460(8) 0.20912(4) 0.0324(2) Uani 1 1 d . . . N1 N 0.5116(3) 0.2613(2) 0.32167(12) 0.0310(5) Uani 1 1 d . . . N2 N 0.4387(3) 0.5363(2) 0.23903(11) 0.0322(5) Uani 1 1 d . . . F1 F 0.62300(18) -0.01320(16) 0.41184(8) 0.0426(4) Uani 1 1 d . . . F2 F 0.3994(2) -0.19896(16) 0.47694(9) 0.0537(4) Uani 1 1 d . . . F3 F 0.0478(2) -0.12532(19) 0.45310(10) 0.0626(5) Uani 1 1 d . . . F4 F -0.07312(19) 0.1376(2) 0.36466(11) 0.0602(5) Uani 1 1 d . . . F5 F 0.15029(18) 0.32638(16) 0.30153(9) 0.0457(4) Uani 1 1 d . . . F6 F 0.4800(2) 0.75269(16) 0.31399(8) 0.0467(4) Uani 1 1 d . . . F7 F 0.6082(2) 0.99752(17) 0.24405(9) 0.0497(4) Uani 1 1 d . . . F8 F 0.6830(2) 1.05235(16) 0.09144(9) 0.0492(4) Uani 1 1 d . . . F9 F 0.6368(2) 0.85689(17) 0.01076(8) 0.0501(4) Uani 1 1 d . . . F10 F 0.5141(2) 0.60852(17) 0.08117(8) 0.0477(4) Uani 1 1 d . . . C1 C 0.7399(3) 0.4729(3) 0.36966(15) 0.0425(6) Uani 1 1 d . . . H1A H 0.8112 0.4559 0.3276 0.064 Uiso 1 1 calc R . . H1B H 0.7814 0.4055 0.4164 0.064 Uiso 1 1 calc R . . H1C H 0.7459 0.5686 0.3745 0.064 Uiso 1 1 calc R . . C2 C 0.3073(4) 0.4738(3) 0.41960(16) 0.0494(7) Uani 1 1 d . . . H2A H 0.2011 0.4568 0.3983 0.074 Uiso 1 1 calc R . . H2B H 0.2949 0.5697 0.4264 0.074 Uiso 1 1 calc R . . H2C H 0.3314 0.4067 0.4685 0.074 Uiso 1 1 calc R . . C3 C 0.7595(3) 0.3387(3) 0.18061(16) 0.0429(7) Uani 1 1 d . . . H3A H 0.8263 0.3722 0.2157 0.064 Uiso 1 1 calc R . . H3B H 0.7719 0.3957 0.1293 0.064 Uiso 1 1 calc R . . H3C H 0.8012 0.2403 0.1829 0.064 Uiso 1 1 calc R . . C4 C 0.3381(4) 0.2971(3) 0.15042(16) 0.0476(7) Uani 1 1 d . . . H4A H 0.2255 0.3127 0.1726 0.071 Uiso 1 1 calc R . . H4B H 0.3654 0.1973 0.1516 0.071 Uiso 1 1 calc R . . H4C H 0.3367 0.3529 0.0981 0.071 Uiso 1 1 calc R . . C5 C 0.3935(3) 0.1618(3) 0.35471(13) 0.0300(5) Uani 1 1 d . . . C6 C 0.4499(3) 0.0256(3) 0.39984(13) 0.0331(6) Uani 1 1 d . . . C7 C 0.3369(4) -0.0703(3) 0.43263(14) 0.0385(6) Uani 1 1 d . . . C8 C 0.1599(3) -0.0335(3) 0.42140(15) 0.0417(6) Uani 1 1 d . . . C9 C 0.0992(3) 0.1011(3) 0.37663(15) 0.0416(7) Uani 1 1 d . . . C10 C 0.2140(3) 0.1954(3) 0.34420(14) 0.0358(6) Uani 1 1 d . . . C11 C 0.5008(3) 0.6694(3) 0.20062(14) 0.0322(6) Uani 1 1 d . . . C12 C 0.5219(3) 0.7740(3) 0.23888(13) 0.0339(6) Uani 1 1 d . . . C13 C 0.5849(3) 0.9012(3) 0.20380(14) 0.0364(6) Uani 1 1 d . . . C14 C 0.6234(3) 0.9292(3) 0.12603(14) 0.0363(6) Uani 1 1 d . . . C15 C 0.6000(3) 0.8299(3) 0.08623(14) 0.0361(6) Uani 1 1 d . . . C16 C 0.5392(3) 0.7022(3) 0.12266(14) 0.0341(6) Uani 1 1 d . . . C17 C 0.0529(5) 0.6606(5) 0.0432(2) 0.0914(13) Uani 1 1 d . . . H17A H 0.0182 0.5676 0.0653 0.137 Uiso 1 1 calc R . . H17B H 0.1661 0.6500 0.0207 0.137 Uiso 1 1 calc R . . H17C H -0.0301 0.7132 0.0041 0.137 Uiso 1 1 calc R . . C18 C 0.0601(4) 0.7401(3) 0.10467(17) 0.0504(8) Uani 1 1 d . . . C19 C 0.0172(4) 0.6781(3) 0.18037(19) 0.0561(9) Uani 1 1 d . . . H19 H -0.0145 0.5858 0.1933 0.067 Uiso 1 1 calc R . . C20 C 0.0218(4) 0.7534(5) 0.2362(2) 0.0674(10) Uani 1 1 d . . . H20 H -0.0059 0.7111 0.2867 0.081 Uiso 1 1 calc R . . C21 C 0.0670(5) 0.8905(5) 0.2178(2) 0.0794(12) Uani 1 1 d . . . H21 H 0.0693 0.9413 0.2555 0.095 Uiso 1 1 calc R . . C22 C 0.1083(4) 0.9510(4) 0.1435(3) 0.0721(11) Uani 1 1 d . . . H22 H 0.1377 1.0441 0.1305 0.087 Uiso 1 1 calc R . . C23 C 0.1069(4) 0.8772(3) 0.08854(19) 0.0560(8) Uani 1 1 d . . . H23 H 0.1383 0.9200 0.0387 0.067 Uiso 1 1 calc R . . HN2 H 0.329(5) 0.546(4) 0.239(2) 0.080 Uiso 1 1 d . . . HN1 H 0.602(5) 0.222(4) 0.330(2) 0.080 Uiso 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 Al1 0.0390(4) 0.0315(4) 0.0307(4) -0.0083(3) 0.0032(3) -0.0085(3) Al2 0.0364(4) 0.0300(4) 0.0330(4) -0.0101(3) 0.0019(3) -0.0079(3) N1 0.0284(10) 0.0277(12) 0.0368(11) -0.0061(9) 0.0011(9) -0.0061(9) N2 0.0353(11) 0.0275(11) 0.0342(11) -0.0073(9) 0.0024(9) -0.0058(9) F1 0.0386(8) 0.0400(9) 0.0454(8) -0.0045(7) -0.0045(6) -0.0018(7) F2 0.0699(11) 0.0330(9) 0.0513(9) 0.0050(7) 0.0007(8) -0.0116(8) F3 0.0619(11) 0.0571(11) 0.0693(12) -0.0052(9) 0.0180(9) -0.0325(9) F4 0.0301(8) 0.0661(12) 0.0819(12) -0.0109(10) 0.0054(8) -0.0121(8) F5 0.0368(8) 0.0376(9) 0.0568(10) -0.0022(7) -0.0032(7) -0.0003(7) F6 0.0683(11) 0.0388(9) 0.0338(8) -0.0111(6) 0.0106(7) -0.0065(8) F7 0.0728(11) 0.0328(9) 0.0489(9) -0.0178(7) 0.0067(8) -0.0129(8) F8 0.0604(10) 0.0341(9) 0.0508(9) -0.0030(7) 0.0073(8) -0.0135(7) F9 0.0692(11) 0.0490(10) 0.0304(8) -0.0046(7) 0.0060(7) -0.0123(8) F10 0.0684(11) 0.0430(10) 0.0355(8) -0.0139(7) -0.0029(7) -0.0119(8) C1 0.0483(16) 0.0425(16) 0.0396(14) -0.0111(12) -0.0007(12) -0.0142(12) C2 0.0544(18) 0.0538(19) 0.0407(15) -0.0140(13) 0.0102(13) -0.0064(14) C3 0.0431(15) 0.0431(17) 0.0443(15) -0.0129(12) 0.0094(12) -0.0098(12) C4 0.0494(17) 0.0466(18) 0.0510(17) -0.0183(13) -0.0054(13) -0.0090(13) C5 0.0338(13) 0.0287(13) 0.0295(12) -0.0094(10) 0.0038(10) -0.0078(10) C6 0.0338(13) 0.0365(15) 0.0307(12) -0.0105(11) 0.0000(10) -0.0061(11) C7 0.0549(16) 0.0299(15) 0.0304(13) -0.0053(11) 0.0028(11) -0.0085(12) C8 0.0454(16) 0.0427(17) 0.0412(15) -0.0107(12) 0.0095(12) -0.0220(12) C9 0.0326(14) 0.0479(17) 0.0458(15) -0.0129(13) 0.0061(11) -0.0088(12) C10 0.0365(14) 0.0340(15) 0.0367(13) -0.0072(11) 0.0029(11) -0.0062(11) C11 0.0307(13) 0.0287(14) 0.0352(13) -0.0050(10) -0.0011(10) -0.0016(10) C12 0.0398(14) 0.0309(14) 0.0299(12) -0.0075(10) 0.0043(10) -0.0005(11) C13 0.0441(15) 0.0262(14) 0.0393(14) -0.0102(11) -0.0017(11) -0.0011(11) C14 0.0368(14) 0.0268(14) 0.0421(14) -0.0025(11) 0.0003(11) -0.0041(10) C15 0.0411(14) 0.0331(15) 0.0319(13) -0.0045(11) 0.0007(11) -0.0026(11) C16 0.0395(14) 0.0301(14) 0.0342(13) -0.0109(11) -0.0038(11) -0.0029(11) C17 0.086(3) 0.097(3) 0.096(3) -0.046(3) -0.020(2) 0.016(2) C18 0.0373(15) 0.0519(19) 0.0595(18) -0.0130(15) -0.0075(13) 0.0030(13) C19 0.0405(16) 0.0467(19) 0.071(2) 0.0080(16) -0.0057(14) -0.0104(13) C20 0.0462(18) 0.096(3) 0.053(2) -0.009(2) 0.0014(15) -0.0009(18) C21 0.065(2) 0.097(3) 0.086(3) -0.047(3) -0.020(2) 0.005(2) C22 0.059(2) 0.050(2) 0.106(3) -0.013(2) -0.017(2) -0.0123(16) C23 0.0482(18) 0.052(2) 0.0579(19) 0.0064(16) 0.0008(14) -0.0096(14) _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 Al1 C2 1.944(3) . ? Al1 C1 1.952(3) . ? Al1 N2 1.999(2) . ? Al1 N1 2.009(2) . ? Al1 Al2 2.8944(12) . ? Al2 C4 1.945(3) . ? Al2 C3 1.955(3) . ? Al2 N2 1.983(2) . ? Al2 N1 1.999(2) . ? N1 C5 1.424(3) . ? N1 F1 2.794(2) . ? N2 C11 1.440(3) . ? N2 F5 3.203(3) . ? F1 C6 1.349(3) . ? F2 C7 1.341(3) . ? F3 C8 1.337(3) . ? F4 C9 1.341(3) . ? F5 C10 1.350(3) . ? F6 C12 1.351(3) . ? F7 C13 1.343(3) . ? F8 C14 1.336(3) . ? F9 C15 1.346(3) . ? F10 C16 1.341(3) . ? C5 C10 1.390(3) . ? C5 C6 1.391(3) . ? C6 C7 1.373(4) . ? C7 C8 1.375(4) . ? C8 C9 1.383(4) . ? C9 C10 1.371(4) . ? C11 C12 1.384(4) . ? C11 C16 1.390(3) . ? C12 C13 1.381(4) . ? C13 C14 1.387(4) . ? C14 C15 1.362(4) . ? C15 C16 1.383(4) . ? C17 C18 1.499(5) . ? C18 C23 1.381(4) . ? C18 C19 1.394(4) . ? C19 C20 1.380(5) . ? C20 C21 1.375(6) . ? C21 C22 1.367(5) . ? C22 C23 1.354(5) . ? 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 Al1 C1 124.14(13) . . ? C2 Al1 N2 114.10(11) . . ? C1 Al1 N2 109.52(10) . . ? C2 Al1 N1 111.71(12) . . ? C1 Al1 N1 105.03(11) . . ? N2 Al1 N1 85.06(9) . . ? C2 Al1 Al2 131.42(10) . . ? C1 Al1 Al2 104.23(9) . . ? N2 Al1 Al2 43.15(6) . . ? N1 Al1 Al2 43.63(6) . . ? C4 Al2 C3 121.16(13) . . ? C4 Al2 N2 113.71(11) . . ? C3 Al2 N2 111.80(11) . . ? C4 Al2 N1 113.32(11) . . ? C3 Al2 N1 105.21(10) . . ? N2 Al2 N1 85.76(9) . . ? C4 Al2 Al1 132.65(10) . . ? C3 Al2 Al1 106.02(9) . . ? N2 Al2 Al1 43.59(6) . . ? N1 Al2 Al1 43.90(6) . . ? C5 N1 Al2 122.77(16) . . ? C5 N1 Al1 120.00(16) . . ? Al2 N1 Al1 92.47(9) . . ? C5 N1 F1 57.33(12) . . ? Al2 N1 F1 134.52(10) . . ? Al1 N1 F1 128.71(10) . . ? C11 N2 Al2 122.26(16) . . ? C11 N2 Al1 119.52(16) . . ? Al2 N2 Al1 93.26(9) . . ? C11 N2 F5 155.66(15) . . ? Al2 N2 F5 73.03(7) . . ? Al1 N2 F5 74.45(7) . . ? C6 F1 N1 61.95(12) . . ? C10 F5 N2 114.87(14) . . ? C10 C5 C6 115.7(2) . . ? C10 C5 N1 121.9(2) . . ? C6 C5 N1 122.3(2) . . ? F1 C6 C7 118.9(2) . . ? F1 C6 C5 118.4(2) . . ? C7 C6 C5 122.7(2) . . ? F2 C7 C6 119.8(2) . . ? F2 C7 C8 120.1(2) . . ? C6 C7 C8 120.1(2) . . ? F3 C8 C7 120.9(2) . . ? F3 C8 C9 120.3(2) . . ? C7 C8 C9 118.7(2) . . ? F4 C9 C10 120.4(2) . . ? F4 C9 C8 119.2(2) . . ? C10 C9 C8 120.4(2) . . ? F5 C10 C9 118.8(2) . . ? F5 C10 C5 118.8(2) . . ? C9 C10 C5 122.4(2) . . ? C12 C11 C16 115.9(2) . . ? C12 C11 N2 121.9(2) . . ? C16 C11 N2 122.2(2) . . ? F6 C12 C13 117.6(2) . . ? F6 C12 C11 119.4(2) . . ? C13 C12 C11 123.0(2) . . ? F7 C13 C12 120.7(2) . . ? F7 C13 C14 120.1(2) . . ? C12 C13 C14 119.2(2) . . ? F8 C14 C15 121.1(2) . . ? F8 C14 C13 119.7(2) . . ? C15 C14 C13 119.2(2) . . ? F9 C15 C14 119.4(2) . . ? F9 C15 C16 120.0(2) . . ? C14 C15 C16 120.7(2) . . ? F10 C16 C15 118.9(2) . . ? F10 C16 C11 119.2(2) . . ? C15 C16 C11 121.9(2) . . ? C23 C18 C19 117.7(3) . . ? C23 C18 C17 121.6(3) . . ? C19 C18 C17 120.7(3) . . ? C20 C19 C18 120.1(3) . . ? C21 C20 C19 120.6(3) . . ? C22 C21 C20 119.1(4) . . ? C23 C22 C21 120.8(4) . . ? C22 C23 C18 121.7(3) . . ? _diffrn_measured_fraction_theta_max 0.917 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.917 _refine_diff_density_max 0.310 _refine_diff_density_min -0.258 _refine_diff_density_rms 0.047