# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2000 # CCDC Number: 440/184 data_nnopt #------------------------------------------------------------------------------ _audit_creation_date 'Mon Jan 24 14:12:03 2000' _audit_creation_method 'from TEXRAY.INF file' _audit_update_record ? #------------------------------------------------------------------------------ _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan' _computing_structure_solution SHELXS86 _computing_structure_refinement 'teXsan' _computing_publication_material 'teXsan' _computing_molecular_graphics ? #------------------------------------------------------------------------------ _chemical_compound_source ? _chemical_name_common ? _chemical_formula_weight 319.42 _chemical_formula_analytical ? _chemical_formula_sum 'C18 H27 N2 O3 ' _chemical_formula_moiety 'C18 H27 N2 O3 ' _chemical_formula_structural ? _chemical_melting_point ? #------------------------------------------------------------------------------ _cell_length_a 11.494(3) _cell_length_b 25.328(3) _cell_length_c 6.1281(5) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1784.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 288.2 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0.0 _cell_measurement_theta_max 0.0 #------------------------------------------------------------------------------ _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21 ' _symmetry_Int_Tables_number 19 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' '1/2-x, -y,1/2+z' '1/2+x,1/2-y, -z' ' -x,1/2+y,1/2-z' #------------------------------------------------------------------------------ _exptl_crystal_description 'plate' _exptl_crystal_colour 'green' _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.050 _exptl_crystal_density_diffrn 1.189 _exptl_crystal_density_meas 'not measured' _exptl_crystal_F_000 692.00 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type none _exptl_special_details ; ? ; #------------------------------------------------------------------------------ _diffrn_special_details ; ? ; _diffrn_ambient_temperature 288.2 _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'Imaging Plate' _diffrn_measurement_device 'Rigaku RAXISII' _diffrn_measurement_method ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_decay_% 0.00 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? _diffrn_reflns_number 1853 _reflns_number_total 1853 _reflns_number_observed 1389 _reflns_observed_criterion >2.0sigma(I) _diffrn_reflns_av_R_equivalents 0.00 _diffrn_reflns_av_sigmaI/netI 0.125 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 0.00 _diffrn_reflns_theta_max 0.00 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 0.00000 _diffrn_orient_matrix_UB_12 0.00000 _diffrn_orient_matrix_UB_13 0.00000 _diffrn_orient_matrix_UB_21 0.00000 _diffrn_orient_matrix_UB_22 0.00000 _diffrn_orient_matrix_UB_23 0.00000 _diffrn_orient_matrix_UB_31 0.00000 _diffrn_orient_matrix_UB_32 0.00000 _diffrn_orient_matrix_UB_33 0.00000 #------------------------------------------------------------------------------ loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source N 0 8 0.006 0.003 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; O 0 12 0.011 0.006 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; C 0 72 0.003 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; H 0 108 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; #------------------------------------------------------------------------------ loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom _atom_site_occupancy _atom_site_refinement_flags O1 0.7228(2) 0.0537(1) 0.1395(4) 0.0213(7) Uani d . 1.00 . O2 1.0100(2) 0.2276(1) -0.4167(5) 0.0283(8) Uani d . 1.00 . O3 1.2560(2) 0.1340(1) 0.0469(5) 0.0239(8) Uani d . 1.00 . N1 1.1014(3) 0.2101(1) -0.3183(6) 0.0178(8) Uani d . 1.00 . N2 1.2181(3) 0.1660(1) -0.0962(5) 0.0184(8) Uani d . 1.00 . C1 0.3413(4) -0.0358(2) 0.0881(8) 0.030(1) Uani d . 1.00 . C2 0.4181(3) 0.0099(2) 0.0056(8) 0.025(1) Uani d . 1.00 . C3 0.5302(4) 0.0162(2) 0.1410(7) 0.0223(10) Uani d . 1.00 . C4 0.5053(4) 0.0407(2) 0.3662(8) 0.037(1) Uani d . 1.00 . C5 0.6170(3) 0.0493(2) 0.0119(7) 0.023(1) Uani d . 1.00 . C6 0.8122(3) 0.0831(2) 0.0551(7) 0.0192(9) Uani d . 1.00 . C7 0.8112(3) 0.1059(2) -0.1509(6) 0.0197(9) Uani d . 1.00 . C8 0.9070(3) 0.1350(2) -0.2187(6) 0.0182(10) Uani d . 1.00 . C9 1.0049(3) 0.1416(1) -0.0838(6) 0.0164(9) Uani d . 1.00 . C10 1.0046(3) 0.1181(2) 0.1218(6) 0.0202(10) Uani d . 1.00 . C11 0.9090(3) 0.0889(2) 0.1894(7) 0.021(1) Uani d . 1.00 . C12 1.1056(3) 0.1719(1) -0.1623(6) 0.0166(8) Uani d . 1.00 . C13 1.2166(3) 0.2375(1) -0.3486(6) 0.0178(9) Uani d . 1.00 . C14 1.2336(4) 0.2473(2) -0.5905(7) 0.025(1) Uani d . 1.00 . C15 1.2082(4) 0.2901(2) -0.2240(7) 0.026(1) Uani d . 1.00 . C16 1.3012(3) 0.1966(2) -0.2425(7) 0.0190(10) Uani d . 1.00 . C17 1.3503(4) 0.1564(2) -0.4067(7) 0.025(1) Uani d . 1.00 . C18 1.3991(4) 0.2205(2) -0.1040(7) 0.026(1) Uani d . 1.00 . H1 0.3201 -0.0294 0.2354 0.0358 Uiso calc . 1.00 . H2 0.2732 -0.0380 0.0007 0.0358 Uiso calc . 1.00 . H3 0.3834 -0.0680 0.0785 0.0358 Uiso calc . 1.00 . H4 0.4389 0.0030 -0.1419 0.0300 Uiso calc . 1.00 . H5 0.3749 0.0417 0.0135 0.0300 Uiso calc . 1.00 . H6 0.5630 -0.0179 0.1629 0.0261 Uiso calc . 1.00 . H7 0.5756 0.0431 0.4471 0.0452 Uiso calc . 1.00 . H8 0.4734 0.0750 0.3477 0.0452 Uiso calc . 1.00 . H9 0.4514 0.0192 0.4431 0.0452 Uiso calc . 1.00 . H10 0.5856 0.0834 -0.0139 0.0276 Uiso calc . 1.00 . H11 0.6334 0.0327 -0.1237 0.0276 Uiso calc . 1.00 . H12 0.7459 0.1016 -0.2445 0.0233 Uiso calc . 1.00 . H13 0.9064 0.1508 -0.3594 0.0219 Uiso calc . 1.00 . H14 1.0699 0.1220 0.2156 0.0244 Uiso calc . 1.00 . H15 0.9094 0.0727 0.3293 0.0258 Uiso calc . 1.00 . H16 1.3061 0.2645 -0.6137 0.0303 Uiso calc . 1.00 . H17 1.2328 0.2146 -0.6663 0.0303 Uiso calc . 1.00 . H18 1.1724 0.2691 -0.6432 0.0303 Uiso calc . 1.00 . H19 1.2795 0.3088 -0.2377 0.0315 Uiso calc . 1.00 . H20 1.1469 0.3107 -0.2834 0.0315 Uiso calc . 1.00 . H21 1.1931 0.2833 -0.0744 0.0315 Uiso calc . 1.00 . H22 1.2884 0.1415 -0.4888 0.0301 Uiso calc . 1.00 . H23 1.4032 0.1735 -0.5022 0.0301 Uiso calc . 1.00 . H24 1.3898 0.1291 -0.3297 0.0301 Uiso calc . 1.00 . H25 1.4409 0.1930 -0.0338 0.0311 Uiso calc . 1.00 . H26 1.4503 0.2400 -0.1952 0.0311 Uiso calc . 1.00 . H27 1.3666 0.2434 0.0028 0.0311 Uiso calc . 1.00 . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O(1) 0.014(1) 0.027(1) 0.023(1) -0.008(1) -0.002(1) 0.006(1) O(2) 0.014(1) 0.035(2) 0.035(2) 0.003(1) -0.003(1) 0.015(2) O(3) 0.018(1) 0.027(2) 0.026(2) 0.000(1) -0.005(1) 0.009(1) N(1) 0.012(1) 0.019(2) 0.022(2) -0.003(1) 0.001(1) 0.006(1) N(2) 0.014(1) 0.020(2) 0.021(2) -0.003(1) 0.002(1) 0.002(1) C(1) 0.019(2) 0.032(2) 0.037(3) -0.006(2) 0.001(2) -0.002(2) C(2) 0.018(2) 0.024(2) 0.034(2) -0.002(2) -0.002(2) -0.001(2) C(3) 0.016(2) 0.022(2) 0.029(2) -0.003(2) 0.003(2) -0.003(2) C(4) 0.032(3) 0.049(3) 0.030(2) -0.008(3) 0.012(2) -0.009(2) C(5) 0.015(2) 0.027(2) 0.026(2) -0.004(2) -0.002(1) 0.002(2) C(6) 0.017(2) 0.017(2) 0.024(2) -0.002(2) 0.004(1) 0.003(2) C(7) 0.018(2) 0.021(2) 0.021(2) -0.001(2) -0.001(2) 0.003(2) C(8) 0.017(2) 0.019(2) 0.019(2) 0.000(2) -0.001(1) 0.000(2) C(9) 0.016(2) 0.014(2) 0.019(2) -0.002(2) 0.001(1) 0.001(2) C(10) 0.016(2) 0.025(2) 0.020(2) -0.001(2) -0.003(2) 0.005(2) C(11) 0.020(2) 0.021(2) 0.023(2) -0.003(2) -0.001(2) 0.006(2) C(12) 0.014(1) 0.018(2) 0.018(2) 0.000(2) 0.001(2) 0.001(1) C(13) 0.011(2) 0.019(2) 0.023(2) -0.003(1) 0.003(2) 0.005(2) C(14) 0.020(2) 0.031(2) 0.024(2) -0.005(2) 0.003(2) 0.005(2) C(15) 0.030(2) 0.017(2) 0.033(2) -0.003(2) 0.001(2) -0.002(2) C(16) 0.009(2) 0.023(2) 0.025(2) -0.003(1) 0.003(1) -0.001(1) C(17) 0.018(2) 0.027(2) 0.029(2) 0.003(2) 0.006(2) -0.006(2) C(18) 0.018(2) 0.033(2) 0.027(2) -0.008(2) -0.006(2) 0.001(2) #------------------------------------------------------------------------------ _refine_special_details ; ? ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme 'w = 1/[\s^2^(Fo) + 0.00002|Fo|^2^]' _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1389 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.0764 _refine_ls_R_factor_obs 0.0669 _refine_ls_wR_factor_all 0.0855 _refine_ls_wR_factor_obs 0.0830 _refine_ls_goodness_of_fit_all 2.047 _refine_ls_goodness_of_fit_obs 1.986 _refine_ls_shift/esd_max 0.2130 _refine_ls_shift/esd_mean 0.0240 _refine_diff_density_min -0.41 _refine_diff_density_max 0.30 #------------------------------------------------------------------------------ _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O(1) C(5) 1.451(7) 1_555 1_555 yes O(1) C(6) 1.370(6) 1_555 1_555 yes O(2) N(1) 1.290(6) 1_555 1_555 yes O(3) N(2) 1.271(6) 1_555 1_555 yes N(1) C(12) 1.361(7) 1_555 1_555 yes N(1) C(13) 1.506(7) 1_555 1_555 yes N(2) C(12) 1.364(7) 1_555 1_555 yes N(2) C(16) 1.523(7) 1_555 1_555 yes C(1) C(2) 1.541(8) 1_555 1_555 yes C(2) C(3) 1.541(8) 1_555 1_555 yes C(3) C(4) 1.541(9) 1_555 1_555 yes C(3) C(5) 1.526(8) 1_555 1_555 yes C(6) C(7) 1.388(8) 1_555 1_555 yes C(6) C(11) 1.391(8) 1_555 1_555 yes C(7) C(8) 1.390(7) 1_555 1_555 yes C(8) C(9) 1.406(7) 1_555 1_555 yes C(9) C(10) 1.394(7) 1_555 1_555 yes C(9) C(12) 1.469(7) 1_555 1_555 yes C(10) C(11) 1.388(8) 1_555 1_555 yes C(13) C(14) 1.515(8) 1_555 1_555 yes C(13) C(15) 1.540(8) 1_555 1_555 yes C(13) C(16) 1.561(8) 1_555 1_555 yes C(16) C(17) 1.540(8) 1_555 1_555 yes C(16) C(18) 1.533(7) 1_555 1_555 yes #------------------------------------------------------------------------------ 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C(5) O(1) C(6) 117.8(4) 1_555 1_555 1_555 yes O(2) N(1) C(12) 127.0(5) 1_555 1_555 1_555 yes O(2) N(1) C(13) 120.0(4) 1_555 1_555 1_555 yes C(12) N(1) C(13) 112.5(4) 1_555 1_555 1_555 yes O(3) N(2) C(12) 126.9(5) 1_555 1_555 1_555 yes O(3) N(2) C(16) 121.1(4) 1_555 1_555 1_555 yes C(12) N(2) C(16) 111.3(4) 1_555 1_555 1_555 yes C(2) C(1) H(1) 109.3(6) 1_555 1_555 1_555 no C(2) C(1) H(2) 109.3(6) 1_555 1_555 1_555 no C(2) C(1) H(3) 109.4(5) 1_555 1_555 1_555 no H(1) C(1) H(2) 109.6(6) 1_555 1_555 1_555 no H(1) C(1) H(3) 109.7(7) 1_555 1_555 1_555 no H(2) C(1) H(3) 109.6(6) 1_555 1_555 1_555 no C(1) C(2) C(3) 112.3(5) 1_555 1_555 1_555 yes C(1) C(2) H(4) 108.6(5) 1_555 1_555 1_555 no C(1) C(2) H(5) 108.7(5) 1_555 1_555 1_555 no C(3) C(2) H(4) 108.7(5) 1_555 1_555 1_555 no C(3) C(2) H(5) 108.8(5) 1_555 1_555 1_555 no H(4) C(2) H(5) 109.6(6) 1_555 1_555 1_555 no C(2) C(3) C(4) 111.7(5) 1_555 1_555 1_555 yes C(2) C(3) C(5) 108.9(5) 1_555 1_555 1_555 yes C(2) C(3) H(6) 108.3(5) 1_555 1_555 1_555 no C(4) C(3) C(5) 111.3(5) 1_555 1_555 1_555 yes C(4) C(3) H(6) 108.3(6) 1_555 1_555 1_555 no C(5) C(3) H(6) 108.2(5) 1_555 1_555 1_555 no C(3) C(4) H(7) 109.5(6) 1_555 1_555 1_555 no C(3) C(4) H(8) 109.5(6) 1_555 1_555 1_555 no C(3) C(4) H(9) 109.5(6) 1_555 1_555 1_555 no H(7) C(4) H(8) 109.5(7) 1_555 1_555 1_555 no H(7) C(4) H(9) 109.4(7) 1_555 1_555 1_555 no H(8) C(4) H(9) 109.4(6) 1_555 1_555 1_555 no O(1) C(5) C(3) 108.1(5) 1_555 1_555 1_555 yes O(1) C(5) H(10) 109.8(5) 1_555 1_555 1_555 no O(1) C(5) H(11) 109.8(5) 1_555 1_555 1_555 no C(3) C(5) H(10) 109.8(5) 1_555 1_555 1_555 no C(3) C(5) H(11) 109.8(5) 1_555 1_555 1_555 no H(10) C(5) H(11) 109.5(6) 1_555 1_555 1_555 no O(1) C(6) C(7) 124.2(5) 1_555 1_555 1_555 yes O(1) C(6) C(11) 115.7(5) 1_555 1_555 1_555 yes C(7) C(6) C(11) 120.1(5) 1_555 1_555 1_555 yes C(6) C(7) C(8) 119.1(5) 1_555 1_555 1_555 yes C(6) C(7) H(12) 120.5(6) 1_555 1_555 1_555 no C(8) C(7) H(12) 120.4(5) 1_555 1_555 1_555 no C(7) C(8) C(9) 121.5(5) 1_555 1_555 1_555 yes C(7) C(8) H(13) 119.2(5) 1_555 1_555 1_555 no C(9) C(8) H(13) 119.3(5) 1_555 1_555 1_555 no C(8) C(9) C(10) 118.6(5) 1_555 1_555 1_555 yes C(8) C(9) C(12) 120.0(5) 1_555 1_555 1_555 yes C(10) C(9) C(12) 121.4(5) 1_555 1_555 1_555 yes C(9) C(10) C(11) 120.0(5) 1_555 1_555 1_555 yes C(9) C(10) H(14) 120.0(6) 1_555 1_555 1_555 no C(11) C(10) H(14) 120.0(5) 1_555 1_555 1_555 no C(6) C(11) C(10) 120.9(5) 1_555 1_555 1_555 yes C(6) C(11) H(15) 119.5(5) 1_555 1_555 1_555 no C(10) C(11) H(15) 119.7(5) 1_555 1_555 1_555 no N(1) C(12) N(2) 108.7(5) 1_555 1_555 1_555 yes N(1) C(12) C(9) 125.0(5) 1_555 1_555 1_555 yes N(2) C(12) C(9) 126.3(5) 1_555 1_555 1_555 yes N(1) C(13) C(14) 108.0(5) 1_555 1_555 1_555 yes N(1) C(13) C(15) 106.4(4) 1_555 1_555 1_555 yes N(1) C(13) C(16) 101.1(4) 1_555 1_555 1_555 yes C(14) C(13) C(15) 110.5(5) 1_555 1_555 1_555 yes C(14) C(13) C(16) 115.9(5) 1_555 1_555 1_555 yes C(15) C(13) C(16) 114.0(5) 1_555 1_555 1_555 yes C(13) C(14) H(16) 109.5(5) 1_555 1_555 1_555 no C(13) C(14) H(17) 109.5(5) 1_555 1_555 1_555 no C(13) C(14) H(18) 109.5(5) 1_555 1_555 1_555 no H(16) C(14) H(17) 109.5(6) 1_555 1_555 1_555 no H(16) C(14) H(18) 109.4(6) 1_555 1_555 1_555 no H(17) C(14) H(18) 109.5(6) 1_555 1_555 1_555 no C(13) C(15) H(19) 109.4(5) 1_555 1_555 1_555 no C(13) C(15) H(20) 109.4(5) 1_555 1_555 1_555 no C(13) C(15) H(21) 109.3(5) 1_555 1_555 1_555 no H(19) C(15) H(20) 109.6(5) 1_555 1_555 1_555 no H(19) C(15) H(21) 109.5(6) 1_555 1_555 1_555 no H(20) C(15) H(21) 109.7(6) 1_555 1_555 1_555 no N(2) C(16) C(13) 101.1(4) 1_555 1_555 1_555 yes N(2) C(16) C(17) 106.1(4) 1_555 1_555 1_555 yes N(2) C(16) C(18) 109.6(5) 1_555 1_555 1_555 yes C(13) C(16) C(17) 113.3(5) 1_555 1_555 1_555 yes C(13) C(16) C(18) 115.3(5) 1_555 1_555 1_555 yes C(17) C(16) C(18) 110.7(5) 1_555 1_555 1_555 yes C(16) C(17) H(22) 109.5(5) 1_555 1_555 1_555 no C(16) C(17) H(23) 109.5(5) 1_555 1_555 1_555 no C(16) C(17) H(24) 109.3(5) 1_555 1_555 1_555 no H(22) C(17) H(23) 109.6(6) 1_555 1_555 1_555 no H(22) C(17) H(24) 109.5(6) 1_555 1_555 1_555 no H(23) C(17) H(24) 109.4(6) 1_555 1_555 1_555 no C(16) C(18) H(25) 109.5(5) 1_555 1_555 1_555 no C(16) C(18) H(26) 109.5(5) 1_555 1_555 1_555 no C(16) C(18) H(27) 109.4(5) 1_555 1_555 1_555 no H(25) C(18) H(26) 109.5(6) 1_555 1_555 1_555 no H(25) C(18) H(27) 109.5(6) 1_555 1_555 1_555 no H(26) C(18) H(27) 109.4(6) 1_555 1_555 1_555 no #------------------------------------------------------------------------------ #------------------------------------------------------------------------------ _publ_requested_journal ' ENTER JOURNAL NAME HERE' _publ_contact_author ; ENTER NAME ENTER ADDRESS ; _publ_contact_letter ; ENTER TEXT OF LETTER ; _publ_requested_coeditor_name ? _publ_contact_author_phone ' ENTER PHONE NUMBER ' _publ_contact_author_fax ' ENTER FAX NUMBER ' _publ_contact_author_email ' ENTER EMAIL ADDRESS ' loop_ _publ_author_name _publ_author_address ' FIRST AUTHORS NAME ' ; FIRST AUTHORS ADDRESS ; _publ_section_title ; ENTER SECTION TITLE ; _publ_section_abstract ; ENTER ABSTRACT ; _publ_section_experimental ; ENTER EXPERIMENTAL SECTION ; _publ_section_comment ; ENTER TEXT ; _publ_section_references ; ENTER OTHER REFERENCES Molecular Structure Corporation. (1995). teXsan. Single Crystal Structure Analysis Software. Version 1.7. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. ; _publ_section_acknowledgements ; ENTER ACKNOWLEDGEMENTS ; _publ_section_table_legends ; ENTER TABLE LEGENDS ; _publ_section_figure_captions ; ENTER FIGURE CAPTIONS #---END ; data_inoue _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H29 F12 Mn N2 O7' _chemical_formula_weight 788.47 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' 'Mn' 'Mn' 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 14.0810(10) _cell_length_b 15.9400(11) _cell_length_c 16.0751(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3608.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 298 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour black _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.452 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1600 _exptl_absorpt_coefficient_mu 0.471 _exptl_absorpt_correction_type emprical _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24325 _diffrn_reflns_av_R_equivalents 0.0912 _diffrn_reflns_av_sigmaI/netI 0.1095 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 28.28 _reflns_number_total 8695 _reflns_number_gt 3674 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.1137P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.03(3) _refine_ls_number_reflns 8695 _refine_ls_number_parameters 451 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1584 _refine_ls_R_factor_gt 0.0690 _refine_ls_wR_factor_ref 0.2100 _refine_ls_wR_factor_gt 0.1692 _refine_ls_goodness_of_fit_ref 0.859 _refine_ls_restrained_S_all 0.859 _refine_ls_shift/su_max 0.014 _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 Mn1 Mn 0.93193(5) 0.83072(5) 0.03403(5) 0.0599(2) Uani 1 1 d . . . O4 O 0.8132(3) 0.9157(2) 0.0286(3) 0.0746(10) Uani 1 1 d . . . O6 O 1.0293(2) 0.7311(2) 0.0528(2) 0.0615(10) Uani 1 1 d . . . O3 O 0.8800(3) 0.8156(3) 0.1594(2) 0.0699(11) Uani 1 1 d . . . N1 N 1.1179(3) 0.7371(3) 0.0724(3) 0.0607(12) Uani 1 1 d . . . O5 O 0.8548(2) 0.7379(2) -0.0324(3) 0.0715(10) Uani 1 1 d . . . O1 O 1.0274(3) 0.9190(3) 0.0916(3) 0.0845(13) Uani 1 1 d . . . O2 O 0.9806(3) 0.8961(3) -0.0766(3) 0.0785(12) Uani 1 1 d . . . C19 C 1.1158(4) 0.7271(4) -0.1165(4) 0.0727(17) Uani 1 1 d . . . H19A H 1.0789 0.6845 -0.0940 0.087 Uiso 1 1 calc R . . C18 C 1.1791(4) 0.7707(4) -0.0679(3) 0.0587(14) Uani 1 1 d . . . C17 C 1.1897(3) 0.7529(3) 0.0195(3) 0.0570(13) Uani 1 1 d . . . C11 C 1.1522(4) 0.7123(4) 0.1571(4) 0.0707(17) Uani 1 1 d . . . C14 C 1.2538(4) 0.7500(5) 0.1550(4) 0.082(2) Uani 1 1 d . . . C23 C 1.2358(4) 0.8324(5) -0.1043(4) 0.0795(17) Uani 1 1 d . . . H23A H 1.2824 0.8578 -0.0720 0.095 Uiso 1 1 calc R . . C7 C 0.8372(4) 0.8674(4) 0.2003(4) 0.0667(15) Uani 1 1 d . . . C21 C 1.1648(6) 0.8134(5) -0.2316(4) 0.093(2) Uani 1 1 d . . . F9 F 0.7672(4) 0.8813(5) 0.3337(3) 0.159(2) Uani 1 1 d . . . C22 C 1.2262(5) 0.8567(5) -0.1841(5) 0.096(2) Uani 1 1 d . . . H22A H 1.2606 0.9016 -0.2055 0.115 Uiso 1 1 calc R . . O7 O 1.1613(4) 0.8405(4) -0.3145(4) 0.1241(19) Uani 1 1 d . . . F8 F 0.8590(5) 0.7803(3) 0.3175(3) 0.149(2) Uani 1 1 d . . . C9 C 0.7776(5) 0.9553(4) 0.0873(4) 0.0751(17) Uani 1 1 d . . . C6 C 0.8438(6) 0.8560(5) 0.2936(5) 0.090(2) Uani 1 1 d . . . F7 F 0.9134(5) 0.9004(4) 0.3244(3) 0.157(2) Uani 1 1 d . . . C8 C 0.7872(5) 0.9358(4) 0.1718(4) 0.0795(18) Uani 1 1 d . . . H8A H 0.7584 0.9707 0.2106 0.095 Uiso 1 1 calc R . . C5 C 1.0062(9) 1.0099(6) -0.1657(6) 0.116(3) Uani 1 1 d . . . C4 C 1.0092(5) 0.9695(5) -0.0797(5) 0.085(2) Uani 1 1 d . . . C20 C 1.1080(5) 0.7486(5) -0.2022(4) 0.091(2) Uani 1 1 d . . . H20A H 1.0664 0.7202 -0.2372 0.110 Uiso 1 1 calc R . . C3 C 1.0400(5) 1.0195(4) -0.0146(6) 0.097(2) Uani 1 1 d . . . H3A H 1.0572 1.0749 -0.0250 0.116 Uiso 1 1 calc R . . C13 C 1.0877(5) 0.7492(5) 0.2230(4) 0.093(2) Uani 1 1 d . . . H13A H 1.0899 0.8093 0.2200 0.140 Uiso 1 1 calc R . . H13B H 1.1086 0.7313 0.2771 0.140 Uiso 1 1 calc R . . H13C H 1.0238 0.7304 0.2139 0.140 Uiso 1 1 calc R . . C2 C 1.0456(5) 0.9890(5) 0.0646(5) 0.089(2) Uani 1 1 d . . . C12 C 1.1509(7) 0.6155(5) 0.1602(5) 0.110(3) Uani 1 1 d . . . H12A H 1.0864 0.5961 0.1604 0.165 Uiso 1 1 calc R . . H12B H 1.1824 0.5967 0.2098 0.165 Uiso 1 1 calc R . . H12C H 1.1832 0.5935 0.1124 0.165 Uiso 1 1 calc R . . C1 C 1.0787(13) 1.0498(10) 0.1312(9) 0.158(5) Uani 1 1 d . . . C15 C 1.3286(5) 0.6961(7) 0.1979(5) 0.133(4) Uani 1 1 d . . . H15A H 1.3890 0.7239 0.1953 0.199 Uiso 1 1 calc R . . H15B H 1.3328 0.6428 0.1704 0.199 Uiso 1 1 calc R . . H15C H 1.3110 0.6877 0.2550 0.199 Uiso 1 1 calc R . . F4 F 0.9287(8) 1.0491(7) -0.1773(5) 0.272(7) Uani 1 1 d . . . C16 C 1.2585(6) 0.8414(6) 0.1848(5) 0.126(3) Uani 1 1 d . . . H16A H 1.3230 0.8607 0.1827 0.189 Uiso 1 1 calc R . . H16B H 1.2354 0.8449 0.2409 0.189 Uiso 1 1 calc R . . H16C H 1.2199 0.8759 0.1493 0.189 Uiso 1 1 calc R . . F5 F 1.0019(8) 0.9588(5) -0.2256(4) 0.193(3) Uani 1 1 d . . . F1 F 1.1034(11) 1.1221(5) 0.1065(7) 0.270(6) Uani 1 1 d . . . N2 N 1.2706(3) 0.7515(3) 0.0637(3) 0.0670(13) Uani 1 1 d . . . C24 C 1.1014(8) 0.7956(7) -0.3677(6) 0.136(3) Uani 1 1 d . . . H24A H 1.0358 0.8020 -0.3504 0.164 Uiso 1 1 calc R . . H24B H 1.1173 0.7364 -0.3664 0.164 Uiso 1 1 calc R . . F3 F 1.1465(10) 1.0281(7) 0.1705(9) 0.299(9) Uani 1 1 d . . . C25 C 1.1152(10) 0.8315(11) -0.4584(7) 0.184(6) Uani 1 1 d . . . H25A H 1.1815 0.8228 -0.4749 0.221 Uiso 1 1 calc R . . C27 C 1.0968(12) 0.9239(12) -0.4548(12) 0.255(11) Uani 1 1 d . . . H27A H 1.1337 0.9502 -0.4112 0.305 Uiso 1 1 calc R . . H27B H 1.0300 0.9354 -0.4456 0.305 Uiso 1 1 calc R . . F2 F 1.0203(11) 1.0636(12) 0.1824(10) 0.386(13) Uani 1 1 d . . . F6 F 1.0669(9) 1.0556(8) -0.1841(5) 0.295(7) Uani 1 1 d . . . C26 C 1.0542(14) 0.7848(11) -0.5157(9) 0.273(11) Uani 1 1 d . . . H26A H 1.0606 0.8074 -0.5707 0.409 Uiso 1 1 calc R . . H26B H 0.9893 0.7894 -0.4980 0.409 Uiso 1 1 calc R . . H26C H 1.0727 0.7268 -0.5159 0.409 Uiso 1 1 calc R . . C28 C 1.130(2) 0.956(2) -0.5460(16) 0.600(17) Uani 1 1 d . . . H28A H 1.1205 1.0157 -0.5500 0.900 Uiso 1 1 calc R . . H28B H 1.0936 0.9283 -0.5881 0.900 Uiso 1 1 calc R . . H28C H 1.1963 0.9437 -0.5538 0.900 Uiso 1 1 calc R . . F11 F 0.6834(7) 1.0722(4) 0.1200(4) 0.228(5) Uani 1 1 d . . . F10 F 0.6526(8) 1.0109(7) 0.0133(7) 0.249(6) Uani 1 1 d . . . C10 C 0.7201(10) 1.0271(8) 0.0641(6) 0.131(4) Uani 1 1 d . . . F12 F 0.7626(9) 1.0771(5) 0.0149(8) 0.262(6) 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 Mn1 0.0454(4) 0.0702(5) 0.0641(5) -0.0040(5) 0.0000(4) -0.0010(4) O4 0.068(2) 0.085(3) 0.071(3) -0.005(2) -0.004(2) 0.021(2) O6 0.0383(18) 0.071(2) 0.075(3) 0.0049(19) 0.0031(15) -0.0022(17) O3 0.066(2) 0.075(3) 0.068(3) -0.008(2) 0.0101(18) 0.012(2) N1 0.047(3) 0.070(3) 0.065(3) 0.003(2) 0.0068(19) 0.001(2) O5 0.0401(18) 0.084(2) 0.091(3) -0.009(3) -0.007(2) -0.0013(17) O1 0.086(3) 0.085(3) 0.082(3) -0.001(3) -0.015(2) -0.023(3) O2 0.071(3) 0.083(3) 0.081(3) -0.002(2) 0.006(2) -0.001(2) C19 0.071(4) 0.072(4) 0.075(4) -0.008(3) -0.001(3) 0.009(3) C18 0.060(3) 0.061(3) 0.055(3) 0.002(3) 0.006(3) 0.015(3) C17 0.035(2) 0.060(3) 0.076(4) -0.002(3) 0.005(2) 0.003(2) C11 0.055(3) 0.099(5) 0.058(4) 0.010(3) 0.000(3) 0.016(3) C14 0.063(4) 0.126(6) 0.055(4) -0.012(4) -0.005(3) 0.023(4) C23 0.074(4) 0.093(4) 0.072(4) 0.025(4) 0.002(3) 0.004(4) C7 0.053(3) 0.074(4) 0.074(4) 0.000(3) 0.000(3) 0.000(3) C21 0.106(6) 0.102(6) 0.071(5) 0.027(4) 0.019(4) 0.019(5) F9 0.149(5) 0.252(7) 0.077(3) 0.011(4) 0.030(3) 0.074(5) C22 0.082(5) 0.093(5) 0.113(6) 0.027(5) 0.005(4) -0.011(4) O7 0.125(4) 0.148(5) 0.100(4) 0.019(4) -0.005(3) -0.005(4) F8 0.257(7) 0.121(4) 0.068(3) 0.025(3) 0.012(3) 0.021(4) C9 0.071(4) 0.078(4) 0.076(5) -0.009(4) 0.001(3) 0.022(3) C6 0.099(5) 0.102(6) 0.069(5) 0.001(4) 0.000(4) 0.019(5) F7 0.191(6) 0.178(5) 0.101(4) 0.002(4) -0.062(4) -0.047(5) C8 0.086(4) 0.081(4) 0.072(5) -0.011(4) -0.002(3) 0.017(4) C5 0.167(10) 0.087(6) 0.093(7) 0.041(6) 0.010(6) 0.009(6) C4 0.076(4) 0.072(5) 0.108(6) 0.000(4) 0.016(4) 0.004(4) C20 0.092(5) 0.119(6) 0.063(4) -0.020(4) -0.013(3) 0.025(5) C3 0.099(6) 0.062(4) 0.130(7) 0.013(5) -0.002(5) -0.010(4) C13 0.072(4) 0.143(7) 0.065(4) 0.008(4) 0.012(3) 0.032(4) C2 0.083(5) 0.078(5) 0.105(6) -0.010(5) 0.001(4) -0.007(4) C12 0.127(7) 0.109(6) 0.094(6) 0.029(5) 0.010(5) 0.024(5) C1 0.167(11) 0.157(11) 0.152(10) -0.054(9) -0.011(9) -0.085(10) C15 0.080(5) 0.230(11) 0.089(5) 0.031(6) -0.007(4) 0.061(6) F4 0.291(11) 0.362(14) 0.163(7) 0.133(8) 0.041(7) 0.199(12) C16 0.092(5) 0.175(9) 0.111(6) -0.079(6) -0.006(4) -0.018(6) F5 0.320(10) 0.171(6) 0.089(4) 0.043(4) 0.020(5) 0.030(7) F1 0.459(18) 0.105(5) 0.247(10) -0.038(5) -0.109(11) -0.075(8) N2 0.048(3) 0.083(3) 0.070(3) -0.011(2) 0.002(2) 0.007(2) C24 0.125(7) 0.139(8) 0.145(9) -0.030(7) -0.029(6) -0.002(6) F3 0.332(15) 0.205(9) 0.361(17) -0.142(10) -0.226(15) 0.026(9) C25 0.191(11) 0.261(16) 0.100(8) 0.090(11) -0.034(7) -0.026(12) C27 0.201(15) 0.30(2) 0.26(2) 0.181(19) -0.068(13) -0.056(15) F2 0.332(16) 0.50(2) 0.325(16) -0.337(17) 0.141(14) -0.211(17) F6 0.326(13) 0.372(14) 0.188(8) 0.175(9) -0.057(8) -0.218(13) C26 0.40(3) 0.27(2) 0.151(12) 0.033(12) -0.142(16) -0.03(2) C28 0.56(3) 0.83(4) 0.40(3) 0.46(4) -0.27(2) -0.520 F11 0.369(11) 0.196(6) 0.119(5) -0.038(4) -0.031(5) 0.212(8) F10 0.242(9) 0.287(12) 0.219(9) -0.063(8) -0.102(8) 0.182(10) C10 0.180(11) 0.134(8) 0.078(6) 0.013(6) -0.005(6) 0.080(8) F12 0.364(15) 0.179(7) 0.243(10) 0.096(8) 0.041(11) 0.148(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mn1 O6 2.120(4) . ? Mn1 O5 2.124(4) . ? Mn1 O4 2.153(4) . ? Mn1 O1 2.155(4) . ? Mn1 O3 2.157(4) . ? Mn1 O2 2.172(5) . ? O4 C9 1.242(7) . ? O6 N1 1.290(5) . ? O3 C7 1.216(7) . ? N1 C17 1.346(6) . ? N1 C11 1.498(7) . ? O5 N2 1.299(5) 4_465 ? O1 C2 1.224(9) . ? O2 C4 1.240(8) . ? C19 C18 1.374(8) . ? C19 C20 1.423(10) . ? C18 C23 1.395(8) . ? C18 C17 1.440(7) . ? C17 N2 1.342(6) . ? C11 C13 1.515(8) . ? C11 C12 1.543(10) . ? C11 C14 1.552(9) . ? C14 N2 1.487(8) . ? C14 C15 1.524(9) . ? C14 C16 1.535(11) . ? C23 C22 1.347(10) . ? C7 C8 1.376(9) . ? C7 C6 1.512(9) . ? C21 C22 1.344(11) . ? C21 C20 1.389(11) . ? C21 O7 1.402(8) . ? F9 C6 1.320(8) . ? O7 C24 1.399(10) . ? F8 C6 1.284(9) . ? C9 C8 1.399(9) . ? C9 C10 1.451(11) . ? C6 F7 1.307(9) . ? C5 F6 1.161(12) . ? C5 F5 1.261(11) . ? C5 F4 1.272(12) . ? C5 C4 1.525(11) . ? C4 C3 1.385(11) . ? C3 C2 1.365(11) . ? C2 C1 1.517(13) . ? C1 F2 1.184(16) . ? C1 F3 1.197(18) . ? C1 F1 1.267(15) . ? N2 O5 1.299(5) 4_565 ? C24 C25 1.578(14) . ? C25 C26 1.463(19) . ? C25 C27 1.50(2) . ? C27 C28 1.62(3) . ? F11 C10 1.263(10) . ? F10 C10 1.280(14) . ? C10 F12 1.273(14) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O6 Mn1 O5 83.12(14) . . ? O6 Mn1 O4 168.30(15) . . ? O5 Mn1 O4 91.19(15) . . ? O6 Mn1 O1 91.41(16) . . ? O5 Mn1 O1 171.90(18) . . ? O4 Mn1 O1 95.23(17) . . ? O6 Mn1 O3 90.16(15) . . ? O5 Mn1 O3 102.64(17) . . ? O4 Mn1 O3 81.09(17) . . ? O1 Mn1 O3 83.27(18) . . ? O6 Mn1 O2 105.76(15) . . ? O5 Mn1 O2 94.79(18) . . ? O4 Mn1 O2 84.83(16) . . ? O1 Mn1 O2 80.91(19) . . ? O3 Mn1 O2 157.73(16) . . ? C9 O4 Mn1 127.0(4) . . ? N1 O6 Mn1 127.2(3) . . ? C7 O3 Mn1 126.7(4) . . ? O6 N1 C17 125.9(4) . . ? O6 N1 C11 121.0(4) . . ? C17 N1 C11 112.4(4) . . ? N2 O5 Mn1 124.8(3) 4_465 . ? C2 O1 Mn1 125.0(5) . . ? C4 O2 Mn1 126.0(5) . . ? C18 C19 C20 118.6(7) . . ? C19 C18 C23 119.2(6) . . ? C19 C18 C17 121.5(6) . . ? C23 C18 C17 119.3(6) . . ? N2 C17 N1 107.4(5) . . ? N2 C17 C18 127.5(5) . . ? N1 C17 C18 125.1(5) . . ? N1 C11 C13 109.8(5) . . ? N1 C11 C12 106.8(6) . . ? C13 C11 C12 111.0(6) . . ? N1 C11 C14 100.1(5) . . ? C13 C11 C14 114.6(6) . . ? C12 C11 C14 113.5(6) . . ? N2 C14 C15 110.2(5) . . ? N2 C14 C16 106.6(6) . . ? C15 C14 C16 111.4(7) . . ? N2 C14 C11 100.0(5) . . ? C15 C14 C11 114.1(7) . . ? C16 C14 C11 113.7(5) . . ? C22 C23 C18 123.1(7) . . ? O3 C7 C8 127.6(6) . . ? O3 C7 C6 115.1(6) . . ? C8 C7 C6 117.2(6) . . ? C22 C21 C20 124.0(7) . . ? C22 C21 O7 113.8(8) . . ? C20 C21 O7 122.2(8) . . ? C21 C22 C23 117.2(7) . . ? C24 O7 C21 116.4(8) . . ? O4 C9 C8 125.8(6) . . ? O4 C9 C10 115.5(7) . . ? C8 C9 C10 118.7(6) . . ? F8 C6 F7 105.7(7) . . ? F8 C6 F9 106.1(7) . . ? F7 C6 F9 105.2(7) . . ? F8 C6 C7 114.8(6) . . ? F7 C6 C7 110.9(7) . . ? F9 C6 C7 113.4(6) . . ? C7 C8 C9 123.3(6) . . ? F6 C5 F5 104.2(11) . . ? F6 C5 F4 106.6(10) . . ? F5 C5 F4 99.4(11) . . ? F6 C5 C4 118.4(11) . . ? F5 C5 C4 114.9(7) . . ? F4 C5 C4 111.4(9) . . ? O2 C4 C3 128.0(7) . . ? O2 C4 C5 115.2(7) . . ? C3 C4 C5 116.8(7) . . ? C21 C20 C19 117.6(7) . . ? C2 C3 C4 121.2(7) . . ? O1 C2 C3 130.1(7) . . ? O1 C2 C1 113.3(9) . . ? C3 C2 C1 116.6(9) . . ? F2 C1 F3 103.9(17) . . ? F2 C1 F1 103.9(18) . . ? F3 C1 F1 102.1(13) . . ? F2 C1 C2 113.4(12) . . ? F3 C1 C2 115.6(15) . . ? F1 C1 C2 116.4(13) . . ? O5 N2 C17 124.5(5) 4_565 . ? O5 N2 C14 122.0(5) 4_565 . ? C17 N2 C14 112.8(4) . . ? O7 C24 C25 107.8(9) . . ? C26 C25 C27 115.0(13) . . ? C26 C25 C24 108.9(12) . . ? C27 C25 C24 107.5(13) . . ? C25 C27 C28 103(2) . . ? F11 C10 F12 106.2(11) . . ? F11 C10 F10 105.4(11) . . ? F12 C10 F10 94.6(9) . . ? F11 C10 C9 119.6(8) . . ? F12 C10 C9 113.1(11) . . ? F10 C10 C9 114.8(11) . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.477 _refine_diff_density_min -0.393 _refine_diff_density_rms 0.068