# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full J.Mater.Chem. _journal_coden_cambridge 1145 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email t-marks@northwestern.edu _publ_contact_author_name 'Hakan Usta' loop_ _publ_author_name 'Hakan Usta' 'Choongik Kim' 'Zhiming Wang' 'Shaofeng Lu' 'Hui Huang' 'Antonio Facchetti' 'Tobin Marks' data_s38w _database_code_depnum_ccdc_archive 'CCDC 852482' #TrackingRef '- ADIF-Br2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H8 Br2 F14 N2 O4' _chemical_formula_weight 838.16 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.2396(2) _cell_length_b 11.2287(4) _cell_length_c 11.5459(5) _cell_angle_alpha 94.362(3) _cell_angle_beta 99.095(2) _cell_angle_gamma 103.466(2) _cell_volume 647.79(4) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6157 _cell_measurement_theta_min 2.75 _cell_measurement_theta_max 33.18 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.723 _exptl_crystal_size_mid 0.084 _exptl_crystal_size_min 0.028 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.149 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 406 _exptl_absorpt_coefficient_mu 3.272 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.4109 _exptl_absorpt_correction_T_max 0.9133 _exptl_absorpt_process_details face-indexed _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14330 _diffrn_reflns_av_R_equivalents 0.0789 _diffrn_reflns_av_sigmaI/netI 0.0673 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 35.52 _reflns_number_total 5032 _reflns_number_gt 3922 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0279P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5032 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0497 _refine_ls_R_factor_gt 0.0334 _refine_ls_wR_factor_ref 0.0732 _refine_ls_wR_factor_gt 0.0692 _refine_ls_goodness_of_fit_ref 0.967 _refine_ls_restrained_S_all 0.967 _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 Br1 Br 1.41618(3) 0.874722(14) 0.663249(15) 0.01678(6) Uani 1 1 d . . . F1 F 0.5192(2) 0.33158(10) 0.15307(10) 0.0248(2) Uani 1 1 d . . . F2 F 0.3004(2) 0.45078(9) 0.06299(10) 0.0252(2) Uani 1 1 d . . . F3 F 0.0083(2) 0.15795(10) 0.12868(10) 0.0291(3) Uani 1 1 d . . . F4 F -0.1365(2) 0.27537(11) 0.00638(10) 0.0275(3) Uani 1 1 d . . . F5 F 0.3308(2) 0.26268(10) -0.09923(9) 0.0226(2) Uani 1 1 d . . . F6 F -0.0129(2) 0.10750(10) -0.12114(11) 0.0296(3) Uani 1 1 d . . . F7 F 0.3431(2) 0.10954(10) 0.00141(11) 0.0272(3) Uani 1 1 d . . . O1 O 0.6967(2) 0.45144(11) 0.40995(11) 0.0199(3) Uani 1 1 d . . . O2 O 1.9342(2) 1.37360(11) 0.77839(12) 0.0200(3) Uani 1 1 d . . . N1 N 0.3535(3) 0.51254(12) 0.29818(13) 0.0150(3) Uani 1 1 d . . . C1 C 0.5963(3) 0.53158(15) 0.37682(15) 0.0153(3) Uani 1 1 d . . . C2 C 0.6884(3) 0.66793(14) 0.40775(15) 0.0143(3) Uani 1 1 d . . . C3 C 0.9136(3) 0.73699(15) 0.47952(15) 0.0148(3) Uani 1 1 d . . . H3 H 1.0394 0.6990 0.5205 0.018 Uiso 1 1 calc R . . C4 C 0.9569(3) 0.86872(14) 0.49190(14) 0.0135(3) Uani 1 1 d . . . C5 C 1.1802(3) 0.94683(15) 0.56680(15) 0.0138(3) Uani 1 1 d . . . C6 C 1.2305(3) 1.07570(15) 0.57605(15) 0.0138(3) Uani 1 1 d . . . C7 C 1.4674(3) 1.15402(15) 0.64874(15) 0.0150(3) Uani 1 1 d . . . H7 H 1.5964 1.1198 0.6925 0.018 Uiso 1 1 calc R . . C8 C 1.5018(3) 1.27769(15) 0.65315(15) 0.0144(3) Uani 1 1 d . . . C9 C 1.7251(3) 1.37852(15) 0.72100(15) 0.0156(3) Uani 1 1 d . . . C10 C 0.1907(3) 0.39226(15) 0.24406(15) 0.0158(3) Uani 1 1 d . . . H10A H 0.0006 0.3943 0.2282 0.019 Uiso 1 1 calc R . . H10B H 0.2104 0.3299 0.2987 0.019 Uiso 1 1 calc R . . C11 C 0.2762(3) 0.35723(15) 0.12959(15) 0.0157(3) Uani 1 1 d . . . C12 C 0.0807(3) 0.24267(15) 0.05496(16) 0.0170(3) Uani 1 1 d . . . C13 C 0.1908(4) 0.17994(16) -0.04308(17) 0.0206(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.01699(9) 0.01422(8) 0.01836(9) 0.00383(6) -0.00098(6) 0.00452(6) F1 0.0124(5) 0.0339(6) 0.0256(6) -0.0076(5) 0.0004(4) 0.0066(4) F2 0.0375(6) 0.0151(4) 0.0223(6) 0.0054(4) 0.0110(5) 0.0006(5) F3 0.0407(7) 0.0170(5) 0.0251(6) 0.0009(4) 0.0139(5) -0.0064(5) F4 0.0145(5) 0.0409(7) 0.0253(6) -0.0066(5) -0.0010(4) 0.0098(5) F5 0.0211(5) 0.0273(5) 0.0203(5) 0.0031(4) 0.0066(4) 0.0058(4) F6 0.0266(6) 0.0280(6) 0.0261(6) -0.0116(5) -0.0015(5) -0.0002(5) F7 0.0317(6) 0.0210(5) 0.0306(6) 0.0007(5) 0.0036(5) 0.0121(5) O1 0.0204(6) 0.0144(5) 0.0239(7) 0.0022(5) 0.0000(5) 0.0051(5) O2 0.0175(6) 0.0190(6) 0.0224(6) 0.0011(5) -0.0005(5) 0.0059(5) N1 0.0149(6) 0.0126(6) 0.0161(7) 0.0004(5) 0.0006(5) 0.0025(5) C1 0.0151(7) 0.0146(7) 0.0159(8) 0.0015(6) 0.0034(6) 0.0028(6) C2 0.0157(7) 0.0136(7) 0.0146(7) 0.0016(6) 0.0046(6) 0.0043(6) C3 0.0169(8) 0.0134(6) 0.0143(8) 0.0024(6) 0.0026(6) 0.0042(6) C4 0.0146(7) 0.0137(6) 0.0134(7) 0.0019(6) 0.0034(6) 0.0049(6) C5 0.0135(7) 0.0152(7) 0.0139(7) 0.0030(6) 0.0033(6) 0.0052(6) C6 0.0139(7) 0.0146(7) 0.0137(7) 0.0014(6) 0.0028(6) 0.0050(6) C7 0.0151(7) 0.0142(7) 0.0157(8) 0.0018(6) 0.0018(6) 0.0041(6) C8 0.0142(7) 0.0153(7) 0.0135(7) 0.0011(6) 0.0026(6) 0.0034(6) C9 0.0162(8) 0.0147(7) 0.0161(8) 0.0015(6) 0.0037(6) 0.0039(6) C10 0.0148(7) 0.0132(7) 0.0180(8) 0.0005(6) 0.0035(6) 0.0011(6) C11 0.0141(7) 0.0147(7) 0.0171(8) 0.0023(6) 0.0023(6) 0.0013(6) C12 0.0144(7) 0.0161(7) 0.0189(8) 0.0007(6) 0.0033(6) 0.0007(6) C13 0.0187(8) 0.0194(8) 0.0206(9) -0.0008(7) 0.0008(7) 0.0013(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C5 1.8954(17) . ? F1 C11 1.361(2) . ? F2 C11 1.3425(19) . ? F3 C12 1.353(2) . ? F4 C12 1.330(2) . ? F5 C13 1.321(2) . ? F6 C13 1.339(2) . ? F7 C13 1.323(2) . ? O1 C1 1.201(2) . ? O2 C9 1.203(2) . ? N1 C9 1.401(2) 2_776 ? N1 C1 1.403(2) . ? N1 C10 1.452(2) . ? C1 C2 1.491(2) . ? C2 C3 1.359(2) . ? C2 C8 1.410(2) 2_776 ? C3 C4 1.436(2) . ? C3 H3 0.9500 . ? C4 C5 1.404(2) . ? C4 C6 1.444(2) 2_776 ? C5 C6 1.402(2) . ? C6 C7 1.438(2) . ? C6 C4 1.444(2) 2_776 ? C7 C8 1.354(2) . ? C7 H7 0.9500 . ? C8 C2 1.410(2) 2_776 ? C8 C9 1.491(2) . ? C9 N1 1.400(2) 2_776 ? C10 C11 1.514(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.544(2) . ? C12 C13 1.544(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 C9 N1 C1 113.47(13) 2_776 . ? C9 N1 C10 122.23(14) 2_776 . ? C1 N1 C10 124.27(14) . . ? O1 C1 N1 125.08(15) . . ? O1 C1 C2 130.08(15) . . ? N1 C1 C2 104.83(14) . . ? C3 C2 C8 121.75(15) . 2_776 ? C3 C2 C1 129.80(16) . . ? C8 C2 C1 108.43(14) 2_776 . ? C2 C3 C4 118.38(15) . . ? C2 C3 H3 120.8 . . ? C4 C3 H3 120.8 . . ? C5 C4 C3 122.14(15) . . ? C5 C4 C6 118.20(14) . 2_776 ? C3 C4 C6 119.64(14) . 2_776 ? C6 C5 C4 122.70(15) . . ? C6 C5 Br1 118.73(12) . . ? C4 C5 Br1 118.53(12) . . ? C5 C6 C7 121.78(15) . . ? C5 C6 C4 119.08(14) . 2_776 ? C7 C6 C4 119.12(14) . 2_776 ? C8 C7 C6 118.32(16) . . ? C8 C7 H7 120.8 . . ? C6 C7 H7 120.8 . . ? C7 C8 C2 122.61(15) . 2_776 ? C7 C8 C9 129.31(16) . . ? C2 C8 C9 108.05(14) 2_776 . ? O2 C9 N1 124.90(15) . 2_776 ? O2 C9 C8 129.99(16) . . ? N1 C9 C8 105.09(14) 2_776 . ? N1 C10 C11 109.94(13) . . ? N1 C10 H10A 109.7 . . ? C11 C10 H10A 109.7 . . ? N1 C10 H10B 109.7 . . ? C11 C10 H10B 109.7 . . ? H10A C10 H10B 108.2 . . ? F2 C11 F1 107.23(13) . . ? F2 C11 C10 110.92(14) . . ? F1 C11 C10 109.80(13) . . ? F2 C11 C12 108.09(14) . . ? F1 C11 C12 107.43(13) . . ? C10 C11 C12 113.13(13) . . ? F4 C12 F3 108.11(14) . . ? F4 C12 C11 108.35(14) . . ? F3 C12 C11 108.00(14) . . ? F4 C12 C13 108.96(15) . . ? F3 C12 C13 107.51(14) . . ? C11 C12 C13 115.68(14) . . ? F5 C13 F7 109.14(15) . . ? F5 C13 F6 108.64(15) . . ? F7 C13 F6 107.70(14) . . ? F5 C13 C12 111.08(14) . . ? F7 C13 C12 110.87(16) . . ? F6 C13 C12 109.33(14) . . ? 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 C9 N1 C1 O1 176.83(18) 2_776 . . . ? C10 N1 C1 O1 -1.0(3) . . . . ? C9 N1 C1 C2 -2.4(2) 2_776 . . . ? C10 N1 C1 C2 179.77(15) . . . . ? O1 C1 C2 C3 1.8(3) . . . . ? N1 C1 C2 C3 -179.10(17) . . . . ? O1 C1 C2 C8 -179.09(19) . . . 2_776 ? N1 C1 C2 C8 0.04(19) . . . 2_776 ? C8 C2 C3 C4 -0.5(3) 2_776 . . . ? C1 C2 C3 C4 178.55(17) . . . . ? C2 C3 C4 C5 178.12(16) . . . . ? C2 C3 C4 C6 -3.2(3) . . . 2_776 ? C3 C4 C5 C6 177.32(16) . . . . ? C6 C4 C5 C6 -1.4(3) 2_776 . . . ? C3 C4 C5 Br1 -4.9(2) . . . . ? C6 C4 C5 Br1 176.35(13) 2_776 . . . ? C4 C5 C6 C7 -176.77(16) . . . . ? Br1 C5 C6 C7 5.5(2) . . . . ? C4 C5 C6 C4 1.4(3) . . . 2_776 ? Br1 C5 C6 C4 -176.34(13) . . . 2_776 ? C5 C6 C7 C8 -179.99(16) . . . . ? C4 C6 C7 C8 1.8(3) 2_776 . . . ? C6 C7 C8 C2 1.9(3) . . . 2_776 ? C6 C7 C8 C9 179.59(16) . . . . ? C7 C8 C9 O2 7.3(3) . . . . ? C2 C8 C9 O2 -174.71(19) 2_776 . . . ? C7 C8 C9 N1 -174.57(18) . . . 2_776 ? C2 C8 C9 N1 3.39(19) 2_776 . . 2_776 ? C9 N1 C10 C11 93.61(19) 2_776 . . . ? C1 N1 C10 C11 -88.69(19) . . . . ? N1 C10 C11 F2 -47.54(18) . . . . ? N1 C10 C11 F1 70.80(17) . . . . ? N1 C10 C11 C12 -169.20(14) . . . . ? F2 C11 C12 F4 -49.16(18) . . . . ? F1 C11 C12 F4 -164.58(14) . . . . ? C10 C11 C12 F4 74.08(18) . . . . ? F2 C11 C12 F3 -166.03(14) . . . . ? F1 C11 C12 F3 78.55(17) . . . . ? C10 C11 C12 F3 -42.79(19) . . . . ? F2 C11 C12 C13 73.48(19) . . . . ? F1 C11 C12 C13 -41.94(19) . . . . ? C10 C11 C12 C13 -163.28(15) . . . . ? F4 C12 C13 F5 80.16(17) . . . . ? F3 C12 C13 F5 -162.90(14) . . . . ? C11 C12 C13 F5 -42.2(2) . . . . ? F4 C12 C13 F7 -158.31(13) . . . . ? F3 C12 C13 F7 -41.37(18) . . . . ? C11 C12 C13 F7 79.38(19) . . . . ? F4 C12 C13 F6 -39.72(19) . . . . ? F3 C12 C13 F6 77.21(18) . . . . ? C11 C12 C13 F6 -162.04(15) . . . . ? _diffrn_measured_fraction_theta_max 0.848 _diffrn_reflns_theta_full 35.52 _diffrn_measured_fraction_theta_full 0.848 _refine_diff_density_max 1.054 _refine_diff_density_min -0.710 _refine_diff_density_rms 0.113 # Attachment '- ADIF-CN2.cif' data_s52z _database_code_depnum_ccdc_archive 'CCDC 852483' #TrackingRef '- ADIF-CN2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C42 H24 F14 N4 O4' _chemical_formula_weight 914.65 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 5.5811(4) _cell_length_b 8.4397(7) _cell_length_c 20.1209(14) _cell_angle_alpha 90.954(6) _cell_angle_beta 91.204(6) _cell_angle_gamma 93.579(7) _cell_volume 945.54(12) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1988 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 29.87 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.606 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 462 _exptl_absorpt_coefficient_mu 0.151 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.9444 _exptl_absorpt_correction_T_max 0.9958 _exptl_absorpt_process_details face-indexed _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13374 _diffrn_reflns_av_R_equivalents 0.3469 _diffrn_reflns_av_sigmaI/netI 0.6482 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 30.76 _reflns_number_total 5543 _reflns_number_gt 1668 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 V2.1-4 (Bruker, 2007)' _computing_cell_refinement 'SAINT V7.23A (Bruker, 2005)' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0359P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_coef 0.015(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5543 _refine_ls_number_parameters 291 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.3874 _refine_ls_R_factor_gt 0.0799 _refine_ls_wR_factor_ref 0.1770 _refine_ls_wR_factor_gt 0.1270 _refine_ls_goodness_of_fit_ref 0.907 _refine_ls_restrained_S_all 0.907 _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 F1 F 0.7428(5) 0.6885(3) -0.06977(12) 0.0575(9) Uani 1 1 d . . . F2 F 0.7724(6) 0.9245(3) -0.02722(13) 0.0639(9) Uani 1 1 d . . . F3 F 0.4417(5) 0.7842(3) -0.02280(12) 0.0474(8) Uani 1 1 d . . . F4 F 1.0035(4) 0.7087(3) 0.04498(12) 0.0537(8) Uani 1 1 d . . . F5 F 0.6714(5) 0.5604(3) 0.04867(11) 0.0443(7) Uani 1 1 d . . . F6 F 0.7922(5) 0.9470(3) 0.11021(11) 0.0414(7) Uani 1 1 d . . . F7 F 0.4581(4) 0.8030(3) 0.11263(11) 0.0376(7) Uani 1 1 d . . . O1 O 1.0591(4) 0.9484(3) 0.25389(12) 0.0246(7) Uani 1 1 d . . . O2 O 0.3559(5) 0.6360(3) 0.24508(12) 0.0241(7) Uani 1 1 d . . . N1 N 0.7159(5) 0.7840(4) 0.23357(15) 0.0206(8) Uani 1 1 d . . . N2 N -0.0818(6) 0.7013(4) 0.49989(17) 0.0286(9) Uani 1 1 d . . . C1 C 0.6772(9) 0.7798(6) -0.0200(2) 0.0366(12) Uani 1 1 d . . . C2 C 0.7624(7) 0.7105(5) 0.0463(2) 0.0290(11) Uani 1 1 d . . . C3 C 0.7004(7) 0.7952(5) 0.11124(19) 0.0235(10) Uani 1 1 d . . . C4 C 0.7885(7) 0.7109(4) 0.17158(18) 0.0223(10) Uani 1 1 d . . . H4A H 0.7245 0.5988 0.1695 0.027 Uiso 1 1 calc R . . H4B H 0.9659 0.7118 0.1711 0.027 Uiso 1 1 calc R . . C5 C 0.8657(7) 0.8929(4) 0.27109(19) 0.0189(9) Uani 1 1 d . . . C6 C 0.7369(7) 0.9169(4) 0.33375(19) 0.0194(9) Uani 1 1 d . . . C7 C 0.8013(7) 1.0145(4) 0.38634(19) 0.0205(10) Uani 1 1 d . . . H7 H 0.9420 1.0838 0.3856 0.025 Uiso 1 1 calc R . . C8 C 0.6495(6) 1.0095(5) 0.4431(2) 0.0210(10) Uani 1 1 d . . . C9 C 0.4402(6) 0.9019(4) 0.44258(18) 0.0178(9) Uani 1 1 d . . . C10 C 0.3789(6) 0.8056(4) 0.38530(18) 0.0194(9) Uani 1 1 d . . . H10 H 0.2382 0.7360 0.3841 0.023 Uiso 1 1 calc R . . C11 C 0.5264(6) 0.8153(4) 0.33222(18) 0.0193(9) Uani 1 1 d . . . C12 C 0.5099(7) 0.7314(5) 0.26710(19) 0.0218(10) Uani 1 1 d . . . C13 C 0.2981(6) 0.8957(4) 0.49977(18) 0.0171(9) Uani 1 1 d . . . C14 C 0.0886(7) 0.7862(5) 0.50008(18) 0.0207(10) Uani 1 1 d . . . C15 C 0.7765(7) 0.3237(5) 0.25038(19) 0.0231(10) Uani 1 1 d . . . C16 C 0.8602(7) 0.4203(5) 0.3038(2) 0.0254(10) Uani 1 1 d . . . H16 H 1.0127 0.4764 0.3016 0.030 Uiso 1 1 calc R . . C17 C 0.7237(7) 0.4359(5) 0.3604(2) 0.0300(11) Uani 1 1 d . . . H17 H 0.7832 0.5018 0.3965 0.036 Uiso 1 1 calc R . . C18 C 0.5009(7) 0.3550(5) 0.3638(2) 0.0281(11) Uani 1 1 d . . . H18 H 0.4065 0.3652 0.4022 0.034 Uiso 1 1 calc R . . C19 C 0.4172(7) 0.2595(5) 0.3109(2) 0.0286(11) Uani 1 1 d . . . H19 H 0.2645 0.2036 0.3132 0.034 Uiso 1 1 calc R . . C20 C 0.5538(7) 0.2441(5) 0.2544(2) 0.0280(11) Uani 1 1 d . . . H20 H 0.4933 0.1783 0.2182 0.034 Uiso 1 1 calc R . . C21 C 0.9269(7) 0.3064(5) 0.1893(2) 0.0333(12) Uani 1 1 d . . . H21A H 1.0577 0.3895 0.1901 0.050 Uiso 1 1 calc R . . H21B H 0.8262 0.3166 0.1493 0.050 Uiso 1 1 calc R . . H21C H 0.9943 0.2019 0.1890 0.050 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 F1 0.066(2) 0.087(2) 0.0190(17) -0.0160(15) 0.0057(14) 0.0045(17) F2 0.092(2) 0.064(2) 0.0299(17) 0.0123(15) -0.0111(15) -0.0389(17) F3 0.0431(18) 0.076(2) 0.0231(16) 0.0066(14) -0.0097(13) 0.0038(15) F4 0.0281(16) 0.106(3) 0.0274(17) -0.0090(15) 0.0008(12) 0.0118(15) F5 0.076(2) 0.0320(17) 0.0230(16) -0.0060(12) -0.0126(13) -0.0073(14) F6 0.073(2) 0.0238(15) 0.0256(16) 0.0024(11) -0.0104(13) -0.0099(13) F7 0.0298(15) 0.0619(19) 0.0227(15) 0.0052(12) 0.0008(11) 0.0153(13) O1 0.0248(16) 0.0253(17) 0.0233(17) 0.0006(13) -0.0034(13) -0.0016(13) O2 0.0279(17) 0.0235(18) 0.0202(17) -0.0041(13) -0.0044(13) -0.0006(13) N1 0.0251(19) 0.021(2) 0.015(2) -0.0028(15) -0.0047(15) -0.0005(15) N2 0.031(2) 0.026(2) 0.029(2) -0.0025(16) -0.0017(17) -0.0011(17) C1 0.041(3) 0.048(3) 0.020(3) -0.001(2) 0.001(2) -0.008(2) C2 0.028(3) 0.038(3) 0.021(3) -0.002(2) 0.001(2) -0.001(2) C3 0.028(2) 0.024(2) 0.018(2) 0.0011(18) -0.0047(19) 0.0003(18) C4 0.030(2) 0.021(2) 0.016(2) -0.0041(17) -0.0010(18) 0.0052(18) C5 0.019(2) 0.020(2) 0.017(2) 0.0005(18) -0.0014(17) 0.0007(17) C6 0.020(2) 0.018(2) 0.020(3) -0.0022(18) -0.0080(18) 0.0049(17) C7 0.020(2) 0.021(2) 0.021(3) 0.0048(19) -0.0031(18) -0.0029(17) C8 0.014(2) 0.022(2) 0.027(3) 0.0015(19) -0.0049(17) 0.0011(17) C9 0.017(2) 0.017(2) 0.019(2) 0.0030(17) -0.0059(17) 0.0028(16) C10 0.021(2) 0.020(2) 0.017(2) -0.0002(18) -0.0078(17) -0.0003(17) C11 0.023(2) 0.020(2) 0.015(2) 0.0017(18) -0.0067(18) 0.0011(17) C12 0.028(3) 0.019(2) 0.018(2) -0.0009(19) -0.0064(19) 0.0030(19) C13 0.019(2) 0.019(2) 0.012(2) -0.0036(17) -0.0067(17) -0.0007(16) C14 0.023(2) 0.026(3) 0.012(2) -0.0031(18) -0.0045(18) -0.0009(19) C15 0.024(2) 0.025(2) 0.021(3) 0.0048(19) -0.0070(19) 0.0062(18) C16 0.017(2) 0.023(2) 0.035(3) 0.001(2) -0.0052(19) -0.0019(18) C17 0.031(3) 0.030(3) 0.029(3) 0.000(2) -0.007(2) 0.002(2) C18 0.028(2) 0.029(3) 0.028(3) 0.009(2) 0.002(2) 0.009(2) C19 0.022(2) 0.026(3) 0.038(3) 0.009(2) -0.002(2) 0.0009(19) C20 0.027(2) 0.028(3) 0.030(3) 0.003(2) -0.007(2) 0.0046(19) C21 0.041(3) 0.029(3) 0.030(3) 0.004(2) -0.002(2) 0.006(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 C1 1.325(5) . ? F2 C1 1.313(5) . ? F3 C1 1.317(5) . ? F4 C2 1.347(4) . ? F5 C2 1.337(4) . ? F6 C3 1.350(4) . ? F7 C3 1.359(4) . ? O1 C5 1.209(4) . ? O2 C12 1.212(4) . ? N1 C12 1.397(4) . ? N1 C5 1.403(5) . ? N1 C4 1.459(5) . ? N2 C14 1.154(4) . ? C1 C2 1.544(6) . ? C2 C3 1.535(5) . ? C3 C4 1.506(5) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.482(5) . ? C6 C7 1.359(6) . ? C6 C11 1.410(5) . ? C7 C8 1.436(5) . ? C7 H7 0.9500 . ? C8 C13 1.405(5) 2_676 ? C8 C9 1.434(5) . ? C9 C13 1.411(5) . ? C9 C10 1.423(5) . ? C10 C11 1.363(5) . ? C10 H10 0.9500 . ? C11 C12 1.477(5) . ? C13 C8 1.405(5) 2_676 ? C13 C14 1.444(5) . ? C15 C20 1.380(5) . ? C15 C16 1.393(6) . ? C15 C21 1.513(5) . ? C16 C17 1.391(5) . ? C16 H16 0.9500 . ? C17 C18 1.384(5) . ? C17 H17 0.9500 . ? C18 C19 1.380(6) . ? C18 H18 0.9500 . ? C19 C20 1.392(5) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12 N1 C5 113.1(3) . . ? C12 N1 C4 122.8(4) . . ? C5 N1 C4 123.2(3) . . ? F2 C1 F3 108.5(4) . . ? F2 C1 F1 109.2(3) . . ? F3 C1 F1 108.2(4) . . ? F2 C1 C2 110.6(4) . . ? F3 C1 C2 111.2(3) . . ? F1 C1 C2 109.1(4) . . ? F5 C2 F4 108.2(3) . . ? F5 C2 C3 107.9(3) . . ? F4 C2 C3 107.1(4) . . ? F5 C2 C1 107.6(4) . . ? F4 C2 C1 107.5(3) . . ? C3 C2 C1 118.2(3) . . ? F6 C3 F7 106.0(3) . . ? F6 C3 C4 111.4(3) . . ? F7 C3 C4 110.2(3) . . ? F6 C3 C2 109.0(3) . . ? F7 C3 C2 108.1(4) . . ? C4 C3 C2 112.0(3) . . ? N1 C4 C3 112.4(3) . . ? N1 C4 H4A 109.1 . . ? C3 C4 H4A 109.1 . . ? N1 C4 H4B 109.1 . . ? C3 C4 H4B 109.1 . . ? H4A C4 H4B 107.8 . . ? O1 C5 N1 125.0(3) . . ? O1 C5 C6 130.0(4) . . ? N1 C5 C6 104.9(3) . . ? C7 C6 C11 122.9(3) . . ? C7 C6 C5 128.8(4) . . ? C11 C6 C5 108.3(3) . . ? C6 C7 C8 117.8(4) . . ? C6 C7 H7 121.1 . . ? C8 C7 H7 121.1 . . ? C13 C8 C9 118.4(3) 2_676 . ? C13 C8 C7 122.1(3) 2_676 . ? C9 C8 C7 119.4(4) . . ? C13 C9 C10 121.5(3) . . ? C13 C9 C8 118.3(3) . . ? C10 C9 C8 120.2(3) . . ? C11 C10 C9 118.5(4) . . ? C11 C10 H10 120.7 . . ? C9 C10 H10 120.7 . . ? C10 C11 C6 121.2(4) . . ? C10 C11 C12 130.7(4) . . ? C6 C11 C12 108.1(3) . . ? O2 C12 N1 125.1(4) . . ? O2 C12 C11 129.5(3) . . ? N1 C12 C11 105.4(3) . . ? C8 C13 C9 123.3(3) 2_676 . ? C8 C13 C14 118.0(3) 2_676 . ? C9 C13 C14 118.7(3) . . ? N2 C14 C13 178.5(4) . . ? C20 C15 C16 118.6(4) . . ? C20 C15 C21 120.7(4) . . ? C16 C15 C21 120.6(4) . . ? C17 C16 C15 121.0(4) . . ? C17 C16 H16 119.5 . . ? C15 C16 H16 119.5 . . ? C18 C17 C16 119.8(4) . . ? C18 C17 H17 120.1 . . ? C16 C17 H17 120.1 . . ? C19 C18 C17 119.4(4) . . ? C19 C18 H18 120.3 . . ? C17 C18 H18 120.3 . . ? C18 C19 C20 120.8(4) . . ? C18 C19 H19 119.6 . . ? C20 C19 H19 119.6 . . ? C15 C20 C19 120.4(4) . . ? C15 C20 H20 119.8 . . ? C19 C20 H20 119.8 . . ? C15 C21 H21A 109.5 . . ? C15 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C15 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? 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 F2 C1 C2 F5 -176.3(3) . . . . ? F3 C1 C2 F5 63.2(4) . . . . ? F1 C1 C2 F5 -56.1(4) . . . . ? F2 C1 C2 F4 -60.0(5) . . . . ? F3 C1 C2 F4 179.5(4) . . . . ? F1 C1 C2 F4 60.2(5) . . . . ? F2 C1 C2 C3 61.3(5) . . . . ? F3 C1 C2 C3 -59.3(5) . . . . ? F1 C1 C2 C3 -178.5(4) . . . . ? F5 C2 C3 F6 179.6(3) . . . . ? F4 C2 C3 F6 63.3(4) . . . . ? C1 C2 C3 F6 -58.2(5) . . . . ? F5 C2 C3 F7 -65.7(4) . . . . ? F4 C2 C3 F7 178.1(3) . . . . ? C1 C2 C3 F7 56.6(4) . . . . ? F5 C2 C3 C4 55.9(4) . . . . ? F4 C2 C3 C4 -60.4(4) . . . . ? C1 C2 C3 C4 178.1(4) . . . . ? C12 N1 C4 C3 94.8(4) . . . . ? C5 N1 C4 C3 -97.1(4) . . . . ? F6 C3 C4 N1 61.7(4) . . . . ? F7 C3 C4 N1 -55.6(4) . . . . ? C2 C3 C4 N1 -176.0(3) . . . . ? C12 N1 C5 O1 176.1(3) . . . . ? C4 N1 C5 O1 6.9(6) . . . . ? C12 N1 C5 C6 -2.5(4) . . . . ? C4 N1 C5 C6 -171.6(3) . . . . ? O1 C5 C6 C7 3.6(7) . . . . ? N1 C5 C6 C7 -177.9(4) . . . . ? O1 C5 C6 C11 -175.0(4) . . . . ? N1 C5 C6 C11 3.4(4) . . . . ? C11 C6 C7 C8 1.7(5) . . . . ? C5 C6 C7 C8 -176.8(3) . . . . ? C6 C7 C8 C13 179.2(4) . . . 2_676 ? C6 C7 C8 C9 0.8(5) . . . . ? C13 C8 C9 C13 -0.4(5) 2_676 . . . ? C7 C8 C9 C13 178.1(3) . . . . ? C13 C8 C9 C10 179.0(3) 2_676 . . . ? C7 C8 C9 C10 -2.4(5) . . . . ? C13 C9 C10 C11 -178.8(3) . . . . ? C8 C9 C10 C11 1.7(5) . . . . ? C9 C10 C11 C6 0.7(5) . . . . ? C9 C10 C11 C12 179.9(4) . . . . ? C7 C6 C11 C10 -2.5(6) . . . . ? C5 C6 C11 C10 176.3(3) . . . . ? C7 C6 C11 C12 178.1(3) . . . . ? C5 C6 C11 C12 -3.1(4) . . . . ? C5 N1 C12 O2 -179.1(4) . . . . ? C4 N1 C12 O2 -10.0(6) . . . . ? C5 N1 C12 C11 0.7(4) . . . . ? C4 N1 C12 C11 169.8(3) . . . . ? C10 C11 C12 O2 2.0(7) . . . . ? C6 C11 C12 O2 -178.6(4) . . . . ? C10 C11 C12 N1 -177.7(3) . . . . ? C6 C11 C12 N1 1.6(4) . . . . ? C10 C9 C13 C8 -179.0(3) . . . 2_676 ? C8 C9 C13 C8 0.5(6) . . . 2_676 ? C10 C9 C13 C14 1.3(5) . . . . ? C8 C9 C13 C14 -179.2(3) . . . . ? C8 C13 C14 N2 86(16) 2_676 . . . ? C9 C13 C14 N2 -94(16) . . . . ? C20 C15 C16 C17 0.4(6) . . . . ? C21 C15 C16 C17 -179.5(3) . . . . ? C15 C16 C17 C18 -0.3(6) . . . . ? C16 C17 C18 C19 0.1(6) . . . . ? C17 C18 C19 C20 -0.2(6) . . . . ? C16 C15 C20 C19 -0.5(6) . . . . ? C21 C15 C20 C19 179.5(3) . . . . ? C18 C19 C20 C15 0.4(6) . . . . ? _diffrn_measured_fraction_theta_max 0.944 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.422 _refine_diff_density_min -0.454 _refine_diff_density_rms 0.105