# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_6 _chemical_formula_sum 'C18 H22 F3 N3 O5' _chemical_formula_moiety 'C18 H22 F3 N3 O5' _chemical_formula_weight 417.38 _chemical_melting_point ? _chemical_absolute_configuration syn #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21 1' _symmetry_space_group_name_Hall 'P 2yb' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,1/2+Y,-Z #------------------------------------------------------------------------------ _cell_length_a 4.979(5) _cell_length_b 10.064(11) _cell_length_c 19.859(19) _cell_angle_alpha 90.0000 _cell_angle_beta 92.52(2) _cell_angle_gamma 90.0000 _cell_volume 994.2(17) _cell_formula_units_Z 2 _cell_measurement_reflns_used 1249 _cell_measurement_theta_min 21.20 _cell_measurement_theta_max 68.25 _cell_measurement_temperature 173 #------------------------------------------------------------------------------ _exptl_crystal_description platelet _exptl_crystal_colour colorless _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.020 _exptl_crystal_density_diffrn 1.394 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 436.00 _exptl_absorpt_coefficient_mu 1.041 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'REQAB (Rigaku, 1998)' _exptl_absorpt_correction_T_min 0.407 _exptl_absorpt_correction_T_max 0.979 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 173 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54187 _diffrn_measurement_device_type 'Rigaku Saturn70' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 29.257 _diffrn_reflns_number 12602 _diffrn_reflns_av_R_equivalents 0.1984 _diffrn_reflns_theta_max 68.31 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 67.00 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 3418 _reflns_number_gt 2365 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.1283 _refine_ls_wR_factor_ref 0.3614 _refine_ls_number_restraints 3 _refine_ls_hydrogen_treatment mixed _refine_ls_number_reflns 3418 _refine_ls_number_parameters 271 _refine_ls_goodness_of_fit_ref 1.197 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.001 _refine_diff_density_max 0.440 _refine_diff_density_min -0.340 _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.106(14) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; F F 0.0727 0.0534 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; N N 0.0311 0.0180 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.0492 0.0322 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 0.6063(8) 1.0657(6) 0.6396(3) 0.1218(16) Uani 1.0 2 d . . . F2 F 0.8610(9) 0.9410(6) 0.58378(19) 0.1200(15) Uani 1.0 2 d . . . F3 F 0.9781(9) 1.1426(6) 0.6047(2) 0.1210(15) Uani 1.0 2 d . . . O6 O 0.3760(18) 0.3354(10) 0.7131(4) 0.160(3) Uani 1.0 2 d . . . O7 O 0.6905(10) 0.4764(7) 0.7509(2) 0.1112(16) Uani 1.0 2 d . . . O15 O 0.4875(8) 0.7245(6) 0.6700(3) 0.1034(14) Uani 1.0 2 d . . . O20 O 1.4157(9) 1.0035(7) 0.7986(3) 0.1130(17) Uani 1.0 2 d . . . O21 O 1.1614(11) 1.1360(8) 0.8605(3) 0.1260(19) Uani 1.0 2 d . . . N1 N 0.6129(11) 0.4524(8) 0.6413(3) 0.1033(17) Uani 1.0 2 d . . . N16 N 0.9308(10) 0.7563(7) 0.6909(3) 0.1001(17) Uani 1.0 2 d . . . N17 N 0.8945(9) 0.8744(7) 0.7275(3) 0.0969(16) Uani 1.0 2 d . . . C2 C 0.7988(12) 0.5625(9) 0.6292(3) 0.0935(17) Uani 1.0 2 d . . . C3 C 0.7780(15) 0.5749(10) 0.5542(4) 0.107(2) Uani 1.0 2 d . . . C4 C 0.6875(13) 0.4389(10) 0.5288(4) 0.106(2) Uani 1.0 2 d . . . C5 C 0.4983(14) 0.3958(11) 0.5797(4) 0.116(3) Uani 1.0 2 d . . . C6 C 0.5447(15) 0.4136(9) 0.7009(4) 0.108(2) Uani 1.0 2 d . . . C8 C 0.608(3) 0.4529(17) 0.8186(5) 0.161(5) Uani 1.0 2 d . . . C9 C 0.770(2) 0.5390(14) 0.8640(4) 0.132(4) Uani 1.0 2 d . . . C10 C 0.742(3) 0.6761(16) 0.8617(5) 0.151(5) Uani 1.0 2 d . . . C11 C 0.905(3) 0.7594(16) 0.9019(6) 0.147(4) Uani 1.0 2 d . . . C12 C 1.090(4) 0.706(3) 0.9456(7) 0.173(5) Uani 1.0 2 d . . . C13 C 1.125(3) 0.569(3) 0.9500(7) 0.180(7) Uani 1.0 2 d . . . C14 C 0.958(3) 0.4808(17) 0.9077(5) 0.152(4) Uani 1.0 2 d . . . C15 C 0.7256(11) 0.6883(8) 0.6662(3) 0.0927(17) Uani 1.0 2 d . . . C18 C 1.0082(14) 0.9908(10) 0.6950(4) 0.105(2) Uani 1.0 2 d . . . C19 C 1.0145(13) 1.1023(9) 0.7476(4) 0.107(2) Uani 1.0 2 d . . . C20 C 1.2283(14) 1.0720(11) 0.8030(4) 0.111(3) Uani 1.0 2 d . . . C22 C 1.3589(18) 1.1187(16) 0.9149(4) 0.148(5) Uani 1.0 2 d . . . C23 C 0.8609(13) 1.0341(10) 0.6329(4) 0.110(3) Uani 1.0 2 d . . . H2 H 0.9857 0.5353 0.6437 0.1122 Uiso 1.0 2 calc R . . H3A H 0.9543 0.5987 0.5364 0.1290 Uiso 1.0 2 calc R . . H3B H 0.6452 0.6439 0.5403 0.1290 Uiso 1.0 2 calc R . . H4A H 0.5968 0.4451 0.4835 0.1268 Uiso 1.0 2 calc R . . H4B H 0.8415 0.3769 0.5268 0.1268 Uiso 1.0 2 calc R . . H5A H 0.3154 0.4310 0.5693 0.1390 Uiso 1.0 2 calc R . . H5B H 0.4898 0.2977 0.5825 0.1390 Uiso 1.0 2 calc R . . H8A H 0.6368 0.3585 0.8310 0.1933 Uiso 1.0 2 calc R . . H8B H 0.4148 0.4737 0.8219 0.1933 Uiso 1.0 2 calc R . . H10 H 0.6086 0.7140 0.8320 0.1811 Uiso 1.0 2 calc R . . H11 H 0.8853 0.8531 0.8985 0.1769 Uiso 1.0 2 calc R . . H12 H 1.1981 0.7633 0.9737 0.2074 Uiso 1.0 2 calc R . . H13 H 1.2580 0.5330 0.9806 0.2166 Uiso 1.0 2 calc R . . H14 H 0.9783 0.3870 0.9101 0.1828 Uiso 1.0 2 calc R . . H16N H 1.102(11) 0.709(10) 0.696(5) 0.14(4) Uiso 1.0 2 d . . . H17N H 0.706(5) 0.848(7) 0.731(4) 0.094(18) Uiso 1.0 2 d . . . H18 H 1.1974 0.9698 0.6838 0.1259 Uiso 1.0 2 calc R . . H19A H 1.0557 1.1879 0.7258 0.1290 Uiso 1.0 2 calc R . . H19B H 0.8363 1.1100 0.7675 0.1290 Uiso 1.0 2 calc R . . H22A H 1.5318 1.1545 0.9016 0.1772 Uiso 1.0 2 calc R . . H22B H 1.3785 1.0239 0.9252 0.1772 Uiso 1.0 2 calc R . . H22C H 1.3009 1.1661 0.9548 0.1772 Uiso 1.0 2 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 F1 0.061(2) 0.188(5) 0.117(3) 0.001(3) 0.0036(16) 0.017(3) F2 0.093(3) 0.170(4) 0.097(3) -0.007(3) 0.0023(17) -0.003(3) F3 0.078(3) 0.170(4) 0.115(3) -0.014(3) 0.0139(18) 0.020(3) O6 0.163(6) 0.175(7) 0.145(5) -0.060(6) 0.057(5) -0.015(4) O7 0.082(3) 0.166(5) 0.086(3) -0.005(3) 0.015(2) 0.003(3) O15 0.049(2) 0.145(4) 0.117(3) -0.003(2) 0.0121(18) -0.013(3) O20 0.051(3) 0.180(5) 0.108(3) 0.003(3) 0.0108(19) -0.010(3) O21 0.097(4) 0.186(6) 0.096(3) -0.001(4) 0.010(3) -0.019(3) N1 0.062(3) 0.156(5) 0.093(3) 0.002(3) 0.009(2) 0.008(3) N16 0.053(3) 0.152(5) 0.095(3) 0.005(3) 0.005(2) -0.010(3) N17 0.051(3) 0.142(5) 0.098(3) -0.004(3) 0.0114(19) -0.002(3) C2 0.053(3) 0.141(5) 0.087(4) 0.011(3) 0.009(2) 0.001(3) C3 0.091(5) 0.136(6) 0.097(4) 0.012(4) 0.017(3) 0.000(4) C4 0.071(4) 0.152(6) 0.095(4) -0.000(4) 0.007(3) 0.004(4) C5 0.065(4) 0.172(8) 0.110(5) 0.012(4) 0.005(3) -0.018(5) C6 0.077(4) 0.128(6) 0.120(5) -0.018(4) 0.024(4) 0.010(4) C8 0.170(10) 0.224(13) 0.091(5) -0.038(10) 0.026(5) 0.020(6) C9 0.109(7) 0.203(12) 0.086(5) -0.009(6) 0.019(4) 0.016(5) C10 0.132(9) 0.216(15) 0.105(6) -0.009(9) 0.012(5) 0.019(7) C11 0.124(8) 0.198(12) 0.121(7) -0.028(8) 0.011(6) 0.012(7) C12 0.152(12) 0.239(16) 0.129(8) -0.016(12) 0.021(7) -0.016(10) C13 0.113(9) 0.31(3) 0.124(8) 0.028(11) 0.021(6) 0.007(11) C14 0.132(8) 0.211(12) 0.117(7) 0.010(9) 0.034(6) 0.003(7) C15 0.052(3) 0.141(6) 0.086(3) -0.002(3) 0.007(2) 0.004(3) C18 0.062(4) 0.159(7) 0.094(4) -0.008(4) 0.010(3) 0.007(4) C19 0.063(4) 0.155(7) 0.105(4) -0.011(4) 0.013(3) -0.013(4) C20 0.066(4) 0.172(7) 0.095(4) -0.013(5) 0.017(3) -0.015(4) C22 0.096(6) 0.246(13) 0.101(5) -0.010(7) 0.000(4) -0.035(6) C23 0.054(4) 0.172(8) 0.103(4) -0.017(4) 0.004(3) 0.006(4) #============================================================================== _computing_data_collection 'CrystalClear-SM Expert 2.0 r2 (Rigaku, 2009)' _computing_cell_refinement 'CrystalClear-SM Expert 2.0 r2' _computing_data_reduction 'CrystalClear-SM Expert 2.0 r2' _computing_structure_solution 'SIR2004 (Burla, et al., 2005)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 F1 C23 1.319(8) yes . . F2 C23 1.353(10) yes . . F3 C23 1.370(11) yes . . O6 C6 1.184(13) yes . . O7 C6 1.360(10) yes . . O7 C8 1.443(11) yes . . O15 C15 1.246(7) yes . . O20 C20 1.167(10) yes . . O21 C20 1.366(10) yes . . O21 C22 1.438(10) yes . . N1 C2 1.470(10) yes . . N1 C5 1.445(10) yes . . N1 C6 1.304(10) yes . . N16 N17 1.409(9) yes . . N16 C15 1.308(8) yes . . N17 C18 1.464(11) yes . . C2 C3 1.494(9) yes . . C2 C15 1.515(11) yes . . C3 C4 1.521(13) yes . . C4 C5 1.477(11) yes . . C8 C9 1.468(17) yes . . C9 C10 1.39(3) yes . . C9 C14 1.377(16) yes . . C10 C11 1.392(18) yes . . C11 C12 1.35(2) yes . . C12 C13 1.40(4) yes . . C13 C14 1.46(3) yes . . C18 C19 1.533(12) yes . . C18 C23 1.472(10) yes . . C19 C20 1.527(10) yes . . N16 H16N 0.98(7) no . . N17 H17N 0.98(3) no . . C2 H2 1.000 no . . C3 H3A 0.990 no . . C3 H3B 0.990 no . . C4 H4A 0.990 no . . C4 H4B 0.990 no . . C5 H5A 0.990 no . . C5 H5B 0.990 no . . C8 H8A 0.990 no . . C8 H8B 0.990 no . . C10 H10 0.950 no . . C11 H11 0.950 no . . C12 H12 0.950 no . . C13 H13 0.950 no . . C14 H14 0.950 no . . C18 H18 1.000 no . . C19 H19A 0.990 no . . C19 H19B 0.990 no . . C22 H22A 0.980 no . . C22 H22B 0.980 no . . C22 H22C 0.980 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C6 O7 C8 116.1(8) yes . . . C20 O21 C22 112.8(7) yes . . . C2 N1 C5 112.7(6) yes . . . C2 N1 C6 124.4(6) yes . . . C5 N1 C6 122.8(7) yes . . . N17 N16 C15 121.3(5) yes . . . N16 N17 C18 112.8(5) yes . . . N1 C2 C3 102.1(6) yes . . . N1 C2 C15 112.6(5) yes . . . C3 C2 C15 113.9(7) yes . . . C2 C3 C4 105.2(7) yes . . . C3 C4 C5 103.0(7) yes . . . N1 C5 C4 103.0(7) yes . . . O6 C6 O7 121.3(8) yes . . . O6 C6 N1 126.9(8) yes . . . O7 C6 N1 111.8(7) yes . . . O7 C8 C9 107.7(11) yes . . . C8 C9 C10 121.0(10) yes . . . C8 C9 C14 118.4(14) yes . . . C10 C9 C14 120.6(11) yes . . . C9 C10 C11 121.6(11) yes . . . C10 C11 C12 119.6(16) yes . . . C11 C12 C13 120.9(16) yes . . . C12 C13 C14 120.0(14) yes . . . C9 C14 C13 117.3(16) yes . . . O15 C15 N16 123.6(7) yes . . . O15 C15 C2 121.6(6) yes . . . N16 C15 C2 114.7(5) yes . . . N17 C18 C19 106.4(6) yes . . . N17 C18 C23 114.7(6) yes . . . C19 C18 C23 110.4(8) yes . . . C18 C19 C20 109.7(7) yes . . . O20 C20 O21 124.5(7) yes . . . O20 C20 C19 126.8(7) yes . . . O21 C20 C19 108.7(7) yes . . . F1 C23 F2 105.7(6) yes . . . F1 C23 F3 106.1(7) yes . . . F1 C23 C18 115.6(6) yes . . . F2 C23 F3 104.1(6) yes . . . F2 C23 C18 112.5(8) yes . . . F3 C23 C18 111.9(6) yes . . . N17 N16 H16N 119(6) no . . . C15 N16 H16N 117(6) no . . . N16 N17 H17N 87(4) no . . . C18 N17 H17N 130(4) no . . . N1 C2 H2 109.330 no . . . C3 C2 H2 109.328 no . . . C15 C2 H2 109.329 no . . . C2 C3 H3A 110.692 no . . . C2 C3 H3B 110.694 no . . . C4 C3 H3A 110.699 no . . . C4 C3 H3B 110.699 no . . . H3A C3 H3B 108.800 no . . . C3 C4 H4A 111.165 no . . . C3 C4 H4B 111.169 no . . . C5 C4 H4A 111.159 no . . . C5 C4 H4B 111.165 no . . . H4A C4 H4B 109.094 no . . . N1 C5 H5A 111.169 no . . . N1 C5 H5B 111.169 no . . . C4 C5 H5A 111.171 no . . . C4 C5 H5B 111.174 no . . . H5A C5 H5B 109.105 no . . . O7 C8 H8A 110.162 no . . . O7 C8 H8B 110.162 no . . . C9 C8 H8A 110.150 no . . . C9 C8 H8B 110.159 no . . . H8A C8 H8B 108.461 no . . . C9 C10 H10 119.174 no . . . C11 C10 H10 119.186 no . . . C10 C11 H11 120.171 no . . . C12 C11 H11 120.179 no . . . C11 C12 H12 119.568 no . . . C13 C12 H12 119.570 no . . . C12 C13 H13 120.006 no . . . C14 C13 H13 120.006 no . . . C9 C14 H14 121.372 no . . . C13 C14 H14 121.365 no . . . N17 C18 H18 108.376 no . . . C19 C18 H18 108.383 no . . . C23 C18 H18 108.381 no . . . C18 C19 H19A 109.730 no . . . C18 C19 H19B 109.730 no . . . C20 C19 H19A 109.716 no . . . C20 C19 H19B 109.715 no . . . H19A C19 H19B 108.199 no . . . O21 C22 H22A 109.468 no . . . O21 C22 H22B 109.472 no . . . O21 C22 H22C 109.469 no . . . H22A C22 H22B 109.472 no . . . H22A C22 H22C 109.471 no . . . H22B C22 H22C 109.475 no . . . 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C6 O7 C8 C9 -174.3(8) no . . . . C8 O7 C6 O6 -6.4(12) no . . . . C8 O7 C6 N1 172.6(9) no . . . . C22 O21 C20 O20 4.6(14) no . . . . C22 O21 C20 C19 -177.1(8) no . . . . C2 N1 C5 C4 20.0(8) no . . . . C5 N1 C2 C3 3.1(8) no . . . . C5 N1 C2 C15 125.7(6) no . . . . C2 N1 C6 O6 171.5(7) no . . . . C2 N1 C6 O7 -7.4(11) no . . . . C6 N1 C2 C3 -173.2(7) no . . . . C6 N1 C2 C15 -50.6(9) no . . . . C5 N1 C6 O6 -4.4(13) no . . . . C5 N1 C6 O7 176.6(7) no . . . . C6 N1 C5 C4 -163.7(7) no . . . . N17 N16 C15 O15 3.5(10) no . . . . N17 N16 C15 C2 -179.0(5) no . . . . C15 N16 N17 C18 -117.5(6) no . . . . N16 N17 C18 C19 -166.7(4) no . . . . N16 N17 C18 C23 70.9(7) no . . . . N1 C2 C3 C4 -24.5(7) no . . . . N1 C2 C15 O15 -40.6(8) no . . . . N1 C2 C15 N16 141.9(5) no . . . . C3 C2 C15 O15 75.1(8) no . . . . C3 C2 C15 N16 -102.5(6) no . . . . C15 C2 C3 C4 -146.1(5) no . . . . C2 C3 C4 C5 37.3(7) no . . . . C3 C4 C5 N1 -34.0(8) no . . . . O7 C8 C9 C10 67.1(13) no . . . . O7 C8 C9 C14 -110.8(10) no . . . . C8 C9 C10 C11 -176.4(9) no . . . . C8 C9 C14 C13 177.2(9) no . . . . C10 C9 C14 C13 -0.7(15) no . . . . C14 C9 C10 C11 1.4(15) no . . . . C9 C10 C11 C12 -1.8(16) no . . . . C10 C11 C12 C13 1(2) no . . . . C11 C12 C13 C14 -1(2) no . . . . C12 C13 C14 C9 0.3(18) no . . . . N17 C18 C19 C20 70.5(6) no . . . . N17 C18 C23 F1 58.8(10) no . . . . N17 C18 C23 F2 -62.8(8) no . . . . N17 C18 C23 F3 -179.6(6) no . . . . C19 C18 C23 F1 -61.4(9) no . . . . C19 C18 C23 F2 177.0(5) no . . . . C19 C18 C23 F3 60.2(8) no . . . . C23 C18 C19 C20 -164.4(6) no . . . . C18 C19 C20 O20 23.1(12) no . . . . C18 C19 C20 O21 -155.1(6) no . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 F1 O15 3.541(9) no . . F1 N17 2.932(8) no . . F1 C19 2.913(8) no . . F2 O15 3.379(8) no . . F2 N16 2.835(8) no . . F2 N17 2.930(7) no . . F2 C15 3.115(9) no . . F3 C19 2.865(9) no . . O6 C2 3.569(12) no . . O6 C5 2.810(11) no . . O6 C8 2.629(14) no . . O7 O15 3.114(9) no . . O7 N16 3.303(10) no . . O7 C2 2.644(8) no . . O7 C5 3.584(9) no . . O7 C10 2.983(14) no . . O7 C14 3.333(12) no . . O7 C15 2.726(10) no . . O15 N1 2.871(10) no . . O15 N17 2.736(8) no . . O15 C3 3.152(10) no . . O15 C6 3.199(11) no . . O20 N17 3.177(8) no . . O20 C18 2.829(9) no . . O20 C22 2.610(12) no . . N1 N16 3.562(10) no . . N1 C8 3.522(11) no . . N16 C3 3.331(10) no . . N16 C23 3.038(12) no . . N17 C10 3.441(14) no . . N17 C20 2.957(11) no . . C3 C6 3.572(12) no . . C4 C6 3.530(11) no . . C5 C15 3.567(13) no . . C6 C15 2.997(12) no . . C9 C12 2.79(3) no . . C10 C13 2.75(2) no . . C11 C14 2.82(3) no . . C15 C18 3.392(12) no . . F1 F3 3.267(7) no . 1_455 F1 O6 3.310(11) no . 1_565 F1 O20 3.396(8) no . 1_455 F1 C5 3.562(13) no . 1_565 F1 C18 3.307(9) no . 1_455 F2 C4 3.453(8) no . 2_656 F2 C4 3.239(9) no . 2_756 F3 F1 3.267(7) no . 1_655 F3 O6 3.456(10) no . 1_665 F3 C3 3.498(9) no . 2_756 F3 C5 3.513(11) no . 1_565 O6 F1 3.310(11) no . 1_545 O6 F3 3.456(10) no . 1_445 O6 C19 3.053(13) no . 1_445 O6 C20 3.297(13) no . 1_445 O15 N16 2.839(7) no . 1_455 O15 N17 3.549(8) no . 1_455 O20 F1 3.396(8) no . 1_655 O20 N17 3.109(8) no . 1_655 O20 C19 3.342(9) no . 1_655 N16 O15 2.839(7) no . 1_655 N17 O15 3.549(8) no . 1_655 N17 O20 3.109(8) no . 1_455 C3 F3 3.498(9) no . 2_746 C4 F2 3.453(8) no . 2_646 C4 F2 3.239(9) no . 2_746 C5 F1 3.562(13) no . 1_545 C5 F3 3.513(11) no . 1_545 C18 F1 3.307(9) no . 1_655 C19 O6 3.053(13) no . 1_665 C19 O20 3.342(9) no . 1_455 C20 O6 3.297(13) no . 1_665 F1 H17N 2.88(7) no . . F1 H18 3.1836 no . . F1 H19A 3.0188 no . . F1 H19B 2.7760 no . . F2 H3B 3.2808 no . . F2 H16N 3.41(9) no . . F2 H17N 3.19(7) no . . F2 H18 2.5575 no . . F3 H18 2.5563 no . . F3 H19A 2.4617 no . . F3 H19B 3.3555 no . . O6 H5A 3.0149 no . . O6 H5B 2.7043 no . . O6 H8A 2.6376 no . . O6 H8B 2.5716 no . . O7 H2 2.7057 no . . O7 H10 2.9221 no . . O7 H14 3.5290 no . . O7 H16N 3.32(9) no . . O15 H2 3.1884 no . . O15 H3B 2.8438 no . . O15 H10 3.2493 no . . O15 H16N 3.09(6) no . . O15 H17N 2.02(6) no . . O20 H18 2.5061 no . . O20 H19A 2.9193 no . . O20 H19B 3.1141 no . . O20 H22A 2.5919 no . . O20 H22B 2.5373 no . . O20 H22C 3.5753 no . . O21 H11 3.2643 no . . O21 H19A 2.7538 no . . O21 H19B 2.4161 no . . N1 H3A 3.1163 no . . N1 H3B 2.7920 no . . N1 H4A 3.1325 no . . N1 H4B 2.6969 no . . N16 H2 2.4339 no . . N16 H3A 3.4608 no . . N16 H3B 3.4465 no . . N16 H10 3.3168 no . . N16 H18 2.5328 no . . N17 H10 3.0327 no . . N17 H11 3.4054 no . . N17 H19A 3.2568 no . . N17 H19B 2.5221 no . . C2 H4A 3.2445 no . . C2 H4B 2.7769 no . . C2 H5A 2.9510 no . . C2 H5B 3.1943 no . . C2 H16N 2.46(9) no . . C2 H17N 3.55(7) no . . C3 H5A 2.7483 no . . C3 H5B 3.1980 no . . C3 H16N 3.46(9) no . . C4 H2 2.8379 no . . C5 H2 3.0335 no . . C5 H3A 3.1991 no . . C5 H3B 2.7255 no . . C6 H2 2.7983 no . . C6 H5A 2.8099 no . . C6 H5B 2.6269 no . . C6 H8A 2.6630 no . . C6 H8B 2.5889 no . . C8 H10 2.6414 no . . C8 H14 2.6151 no . . C9 H11 3.2794 no . . C9 H13 3.2808 no . . C10 H8A 3.2916 no . . C10 H8B 2.7049 no . . C10 H12 3.2281 no . . C10 H14 3.2656 no . . C10 H17N 3.12(7) no . . C11 H13 3.2380 no . . C11 H22B 3.5733 no . . C12 H10 3.2190 no . . C12 H14 3.3325 no . . C12 H22B 3.5337 no . . C13 H11 3.2462 no . . C14 H8A 2.4862 no . . C14 H8B 3.1337 no . . C14 H10 3.2508 no . . C14 H12 3.3303 no . . C15 H3A 3.0019 no . . C15 H3B 2.5543 no . . C15 H10 3.3792 no . . C15 H17N 2.06(7) no . . C18 H16N 2.87(10) no . . C19 H17N 3.00(6) no . . C20 H11 3.4145 no . . C20 H18 2.5793 no . . C20 H22A 2.5585 no . . C20 H22B 2.5552 no . . C20 H22C 3.1665 no . . C22 H11 3.5700 no . . C23 H17N 2.83(7) no . . C23 H19A 2.5658 no . . C23 H19B 2.7876 no . . H2 H3A 2.2227 no . . H2 H3B 2.8245 no . . H2 H4B 2.8801 no . . H2 H16N 2.1057 no . . H3A H4A 2.5486 no . . H3A H4B 2.3072 no . . H3A H16N 3.4149 no . . H3B H4A 2.3032 no . . H3B H4B 2.8751 no . . H3B H5A 2.7749 no . . H4A H5A 2.2574 no . . H4A H5B 2.5381 no . . H4B H5A 2.8396 no . . H4B H5B 2.2575 no . . H8A H10 3.5809 no . . H8A H14 2.2810 no . . H8B H10 2.6084 no . . H8B H14 3.3557 no . . H10 H11 2.3332 no . . H10 H17N 2.4834 no . . H11 H12 2.2939 no . . H11 H17N 3.4092 no . . H11 H22B 3.0251 no . . H12 H13 2.3403 no . . H12 H22B 2.9473 no . . H13 H14 2.4273 no . . H16N H17N 2.54(9) no . . H16N H18 2.6809 no . . H17N H18 2.9262 no . . H17N H19B 2.8064 no . . H18 H19A 2.4629 no . . H18 H19B 2.8725 no . . F1 H4A 2.8736 no . 2_656 F1 H5B 2.6489 no . 1_565 F1 H18 2.4506 no . 1_455 F1 H19A 3.5176 no . 1_455 F2 H3A 3.0420 no . 2_756 F2 H4A 2.5916 no . 2_656 F2 H4A 3.0649 no . 2_756 F2 H4B 2.7784 no . 2_756 F2 H5A 3.1293 no . 2_656 F3 H3A 2.8712 no . 2_756 F3 H3B 3.5048 no . 2_756 F3 H4A 3.4393 no . 2_756 F3 H4B 2.8851 no . 1_565 F3 H5A 3.4413 no . 1_665 F3 H5B 2.9063 no . 1_565 F3 H5B 3.0367 no . 1_665 O6 H2 3.0804 no . 1_455 O6 H19A 2.2015 no . 1_445 O6 H19B 3.3685 no . 1_545 O7 H19A 3.4732 no . 1_545 O15 H2 3.1666 no . 1_455 O15 H16N 2.02(6) no . 1_455 O15 H18 2.8793 no . 1_455 O20 H10 3.1294 no . 1_655 O20 H11 3.3597 no . 1_655 O20 H17N 2.56(6) no . 1_655 O20 H19B 2.4561 no . 1_655 O21 H8A 3.4708 no . 1_565 O21 H8A 3.3296 no . 1_665 O21 H14 2.8745 no . 1_565 O21 H22A 3.2787 no . 1_455 N1 H2 3.2348 no . 1_455 C2 H5A 3.1710 no . 1_655 C3 H5A 3.0455 no . 1_655 C4 H5A 3.1949 no . 1_655 C5 H2 3.2220 no . 1_455 C5 H3A 3.4697 no . 1_455 C5 H3B 3.5314 no . 2_646 C5 H4B 3.3959 no . 1_455 C6 H2 3.2030 no . 1_455 C6 H19A 3.3822 no . 1_445 C6 H19A 3.4303 no . 1_545 C8 H22A 3.4545 no . 1_445 C9 H8B 3.4150 no . 1_655 C9 H13 3.5199 no . 1_455 C11 H22C 3.2065 no . 2_747 C12 H10 3.5024 no . 1_655 C12 H14 3.4247 no . 2_757 C12 H22A 3.5403 no . 2_847 C12 H22C 2.8646 no . 2_747 C12 H22C 3.5702 no . 2_847 C13 H8B 3.1285 no . 1_655 C13 H22A 3.4498 no . 2_847 C13 H22B 3.4515 no . 2_847 C13 H22C 3.0628 no . 2_747 C13 H22C 3.4947 no . 2_847 C14 H8B 2.8998 no . 1_655 C14 H12 3.3336 no . 2_747 C14 H22C 3.5929 no . 2_747 C15 H16N 3.19(6) no . 1_455 C20 H8A 3.5581 no . 1_665 C20 H19B 3.1613 no . 1_655 C22 H8A 3.2735 no . 1_665 C22 H12 3.3846 no . 2_857 C22 H13 2.8882 no . 2_857 C22 H14 3.2978 no . 1_565 C23 H3A 3.5847 no . 2_756 C23 H4A 3.2985 no . 2_656 C23 H5B 3.3608 no . 1_565 C23 H18 3.5562 no . 1_455 H2 O6 3.0804 no . 1_655 H2 O15 3.1666 no . 1_655 H2 N1 3.2348 no . 1_655 H2 C5 3.2220 no . 1_655 H2 C6 3.2030 no . 1_655 H2 H5A 2.4879 no . 1_655 H3A F2 3.0420 no . 2_746 H3A F3 2.8712 no . 2_746 H3A C5 3.4697 no . 1_655 H3A C23 3.5847 no . 2_746 H3A H3B 3.4673 no . 1_655 H3A H4B 3.2503 no . 2_756 H3A H5A 2.5309 no . 1_655 H3B F3 3.5048 no . 2_746 H3B C5 3.5314 no . 2_656 H3B H3A 3.4673 no . 1_455 H3B H4A 3.2891 no . 2_656 H3B H4B 3.5868 no . 2_656 H3B H5B 2.9420 no . 2_656 H4A F1 2.8736 no . 2_646 H4A F2 2.5916 no . 2_646 H4A F2 3.0649 no . 2_746 H4A F3 3.4393 no . 2_746 H4A C23 3.2985 no . 2_646 H4A H3B 3.2891 no . 2_646 H4A H18 3.5288 no . 2_746 H4B F2 2.7784 no . 2_746 H4B F3 2.8851 no . 1_545 H4B C5 3.3959 no . 1_655 H4B H3A 3.2503 no . 2_746 H4B H3B 3.5868 no . 2_646 H4B H5A 2.5304 no . 1_655 H4B H5B 3.4593 no . 1_655 H5A F2 3.1293 no . 2_646 H5A F3 3.4413 no . 1_445 H5A C2 3.1710 no . 1_455 H5A C3 3.0455 no . 1_455 H5A C4 3.1949 no . 1_455 H5A H2 2.4879 no . 1_455 H5A H3A 2.5309 no . 1_455 H5A H4B 2.5304 no . 1_455 H5B F1 2.6489 no . 1_545 H5B F3 3.0367 no . 1_445 H5B F3 2.9063 no . 1_545 H5B C23 3.3608 no . 1_545 H5B H3B 2.9420 no . 2_646 H5B H4B 3.4593 no . 1_455 H8A O21 3.3296 no . 1_445 H8A O21 3.4708 no . 1_545 H8A C20 3.5581 no . 1_445 H8A C22 3.2735 no . 1_445 H8A H19A 3.4702 no . 1_545 H8A H19B 2.9898 no . 1_545 H8A H22A 2.5533 no . 1_445 H8A H22C 3.5998 no . 1_445 H8B C9 3.4150 no . 1_455 H8B C13 3.1285 no . 1_455 H8B C14 2.8998 no . 1_455 H8B H13 3.3334 no . 1_455 H8B H14 2.9799 no . 1_455 H10 O20 3.1294 no . 1_455 H10 C12 3.5024 no . 1_455 H10 H12 3.5836 no . 1_455 H11 O20 3.3597 no . 1_455 H11 H13 3.1143 no . 2_757 H11 H22A 3.5088 no . 1_455 H11 H22B 3.1185 no . 1_455 H12 C14 3.3336 no . 2_757 H12 C22 3.3846 no . 2_847 H12 H10 3.5836 no . 1_655 H12 H14 2.7987 no . 2_757 H12 H22A 2.9759 no . 2_847 H12 H22C 3.0753 no . 2_747 H12 H22C 2.9808 no . 2_847 H13 C9 3.5199 no . 1_655 H13 C22 2.8882 no . 2_847 H13 H8B 3.3334 no . 1_655 H13 H11 3.1143 no . 2_747 H13 H22A 2.8013 no . 2_847 H13 H22B 2.5461 no . 2_847 H13 H22C 3.3903 no . 2_747 H13 H22C 2.8303 no . 2_847 H14 O21 2.8745 no . 1_545 H14 C12 3.4247 no . 2_747 H14 C22 3.2978 no . 1_545 H14 H8B 2.9799 no . 1_655 H14 H12 2.7987 no . 2_747 H14 H22A 3.2274 no . 1_445 H14 H22C 2.8621 no . 1_545 H16N O15 2.02(6) no . 1_655 H16N C15 3.19(6) no . 1_655 H16N H17N 3.36(8) no . 1_655 H17N O20 2.56(6) no . 1_455 H17N H16N 3.36(8) no . 1_455 H17N H18 2.9319 no . 1_455 H18 F1 2.4506 no . 1_655 H18 O15 2.8793 no . 1_655 H18 C23 3.5562 no . 1_655 H18 H4A 3.5288 no . 2_756 H18 H17N 2.9319 no . 1_655 H19A F1 3.5176 no . 1_655 H19A O6 2.2015 no . 1_665 H19A O7 3.4732 no . 1_565 H19A C6 3.4303 no . 1_565 H19A C6 3.3822 no . 1_665 H19A H8A 3.4702 no . 1_565 H19B O6 3.3685 no . 1_565 H19B O20 2.4561 no . 1_455 H19B C20 3.1613 no . 1_455 H19B H8A 2.9898 no . 1_565 H19B H22A 3.1531 no . 1_455 H22A O21 3.2787 no . 1_655 H22A C8 3.4545 no . 1_665 H22A C12 3.5403 no . 2_857 H22A C13 3.4498 no . 2_857 H22A H8A 2.5533 no . 1_665 H22A H11 3.5088 no . 1_655 H22A H12 2.9759 no . 2_857 H22A H13 2.8013 no . 2_857 H22A H14 3.2274 no . 1_665 H22A H19B 3.1531 no . 1_655 H22B C13 3.4515 no . 2_857 H22B H11 3.1185 no . 1_655 H22B H13 2.5461 no . 2_857 H22C C11 3.2065 no . 2_757 H22C C12 2.8646 no . 2_757 H22C C12 3.5702 no . 2_857 H22C C13 3.0628 no . 2_757 H22C C13 3.4947 no . 2_857 H22C C14 3.5929 no . 2_757 H22C H8A 3.5998 no . 1_665 H22C H12 3.0753 no . 2_757 H22C H12 2.9808 no . 2_857 H22C H13 3.3903 no . 2_757 H22C H13 2.8303 no . 2_857 H22C H14 2.8621 no . 1_565 #============================================================================== loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_distance_DA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_angle_DHA _geom_hbond_publ_flag N16 H16N O15 . . 1_655 2.839(7) 0.980 2.02(7) 140(8) no N17 H17N O15 . . . 2.736(8) 0.980 2.02(3) 128(5) no #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #============================================================================== _database_code_depnum_ccdc_archive 'CCDC 915107' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_11 #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C23 H22 N2 O3' _chemical_formula_moiety 'C23 H22 N2 O3' _chemical_formula_weight 374.44 _chemical_melting_point ? _chemical_absolute_configuration ad #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21 1' _symmetry_space_group_name_Hall 'P 2yb' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,1/2+Y,-Z #------------------------------------------------------------------------------ _cell_length_a 12.210(8) _cell_length_b 6.164(3) _cell_length_c 12.946(7) _cell_angle_alpha 90.0000 _cell_angle_beta 99.737(12) _cell_angle_gamma 90.0000 _cell_volume 960.3(9) _cell_formula_units_Z 2 _cell_measurement_reflns_used 1174 _cell_measurement_theta_min 21.68 _cell_measurement_theta_max 68.25 _cell_measurement_temperature 173 #------------------------------------------------------------------------------ _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.100 _exptl_crystal_size_mid 0.030 _exptl_crystal_size_min 0.030 _exptl_crystal_density_diffrn 1.295 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 396.00 _exptl_absorpt_coefficient_mu 0.697 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Rigaku (1998). REQAB.Rigaku Corporation, Tokyo, Japan.' _exptl_absorpt_correction_T_min 0.816 _exptl_absorpt_correction_T_max 0.979 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 173 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54187 _diffrn_measurement_device_type 'Rigaku Saturn70' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 11901 _diffrn_reflns_av_R_equivalents 0.0428 _diffrn_reflns_theta_min 3.673 _diffrn_reflns_theta_max 68.121 _diffrn_reflns_theta_full 67.000 _diffrn_measured_fraction_theta_max 0.982 _diffrn_measured_fraction_theta_full 0.988 _diffrn_reflns_Laue_measured_fraction_max 0.982 _diffrn_reflns_Laue_measured_fraction_full 0.988 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 3354 _reflns_number_gt 3160 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0340 _refine_ls_wR_factor_ref 0.0900 _refine_ls_number_restraints 2 _refine_ls_hydrogen_treatment mixed _refine_ls_number_reflns 3354 _refine_ls_number_parameters 257 _refine_ls_goodness_of_fit_ref 0.977 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0609P)^2^+0.0720P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_diff_density_max 0.130 _refine_diff_density_min -0.170 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Parsons and Flack (2004), Acta Cryst. A60, s61' _refine_ls_abs_structure_Flack 0.04(11) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.0311 0.0180 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.0492 0.0322 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 O5 O 0.66606(14) 1.2138(3) 0.23497(13) 0.0461(5) Uani 1.0 2 d . . . O6 O 0.57712(13) 0.6466(3) 0.05881(12) 0.0401(4) Uani 1.0 2 d . . . O13 O 1.00511(14) 0.8507(3) -0.38236(12) 0.0443(5) Uani 1.0 2 d . . . N1 N 0.55041(14) 0.9381(3) 0.15667(13) 0.0274(4) Uani 1.0 2 d . . . N2 N 0.43314(14) 0.8908(4) 0.13769(13) 0.0295(4) Uani 1.0 2 d . . . C3 C 0.38486(18) 1.0542(4) 0.20194(16) 0.0291(5) Uani 1.0 2 d . . . C4 C 0.46495(19) 1.2454(4) 0.21081(19) 0.0349(6) Uani 1.0 2 d . . . C5 C 0.57411(18) 1.1414(4) 0.20340(16) 0.0319(5) Uani 1.0 2 d . . . C6 C 0.61909(18) 0.7958(4) 0.11278(15) 0.0289(5) Uani 1.0 2 d . . . C7 C 0.74343(17) 0.8356(4) 0.13780(15) 0.0306(5) Uani 1.0 2 d . . . C8 C 0.79894(17) 0.7895(4) 0.04293(16) 0.0282(5) Uani 1.0 2 d . . . C9 C 0.79364(17) 0.9452(4) -0.03365(16) 0.0297(5) Uani 1.0 2 d . . . C10 C 0.84747(17) 0.9188(4) -0.12190(16) 0.0276(5) Uani 1.0 2 d . . . C11 C 0.84166(19) 1.0791(4) -0.20138(17) 0.0334(5) Uani 1.0 2 d . . . C12 C 0.8953(2) 1.0497(5) -0.28480(17) 0.0364(6) Uani 1.0 2 d . . . C13 C 0.95743(19) 0.8584(4) -0.29367(16) 0.0335(6) Uani 1.0 2 d . . . C14 C 0.96533(18) 0.7005(4) -0.21857(16) 0.0308(5) Uani 1.0 2 d . . . C15 C 0.90925(17) 0.7267(4) -0.13065(15) 0.0268(5) Uani 1.0 2 d . . . C16 C 0.91328(17) 0.5671(4) -0.05183(16) 0.0297(5) Uani 1.0 2 d . . . C17 C 0.85909(18) 0.5969(4) 0.03216(17) 0.0301(5) Uani 1.0 2 d . . . C18 C 1.0677(3) 0.6612(6) -0.39707(19) 0.0522(7) Uani 1.0 2 d . . . C19 C 0.78881(19) 0.7044(5) 0.23648(16) 0.0398(6) Uani 1.0 2 d . . . C20 C 0.37156(17) 0.9673(4) 0.30898(16) 0.0282(5) Uani 1.0 2 d . . . C21 C 0.4235(2) 0.7794(4) 0.35165(17) 0.0358(6) Uani 1.0 2 d . . . C22 C 0.4079(3) 0.7076(5) 0.44965(19) 0.0478(7) Uani 1.0 2 d . . . C23 C 0.3409(3) 0.8228(6) 0.50595(19) 0.0545(8) Uani 1.0 2 d . . . C24 C 0.2898(3) 1.0107(6) 0.4649(2) 0.0548(9) Uani 1.0 2 d . . . C25 C 0.30617(19) 1.0824(5) 0.36702(18) 0.0416(6) Uani 1.0 2 d . . . H3 H 0.3107 1.1013 0.1635 0.0349 Uiso 1.0 2 calc R . . H4A H 0.4431 1.3501 0.1530 0.0419 Uiso 1.0 2 calc R . . H4B H 0.4679 1.3214 0.2786 0.0419 Uiso 1.0 2 calc R . . H7 H 0.7549 0.9927 0.1556 0.0367 Uiso 1.0 2 calc R . . H9 H 0.7528 1.0744 -0.0274 0.0356 Uiso 1.0 2 calc R . . H11 H 0.8001 1.2079 -0.1965 0.0400 Uiso 1.0 2 calc R . . H12 H 0.8910 1.1585 -0.3373 0.0436 Uiso 1.0 2 calc R . . H14 H 1.0079 0.5736 -0.2247 0.0369 Uiso 1.0 2 calc R . . H16 H 0.9540 0.4373 -0.0568 0.0356 Uiso 1.0 2 calc R . . H17 H 0.8621 0.4863 0.0837 0.0361 Uiso 1.0 2 calc R . . H18A H 1.0193 0.5335 -0.4011 0.0627 Uiso 1.0 2 calc R . . H18B H 1.1289 0.6451 -0.3380 0.0627 Uiso 1.0 2 calc R . . H18C H 1.0978 0.6746 -0.4623 0.0627 Uiso 1.0 2 calc R . . H19A H 0.7743 0.5498 0.2228 0.0478 Uiso 1.0 2 calc R . . H19B H 0.7521 0.7515 0.2944 0.0478 Uiso 1.0 2 calc R . . H19C H 0.8691 0.7282 0.2553 0.0478 Uiso 1.0 2 calc R . . H21 H 0.4699 0.6997 0.3135 0.0429 Uiso 1.0 2 calc R . . H22 H 0.4435 0.5786 0.4782 0.0574 Uiso 1.0 2 calc R . . H23 H 0.3300 0.7726 0.5729 0.0655 Uiso 1.0 2 calc R . . H24 H 0.2437 1.0906 0.5034 0.0657 Uiso 1.0 2 calc R . . H25 H 0.2717 1.2131 0.3394 0.0499 Uiso 1.0 2 calc R . . H2 H 0.410(3) 0.933(5) 0.0644(9) 0.061(9) Uiso 1.0 2 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O5 0.0374(10) 0.0457(10) 0.0564(10) -0.0101(9) 0.0111(8) -0.0217(9) O6 0.0374(9) 0.0426(10) 0.0417(9) -0.0086(9) 0.0108(7) -0.0176(8) O13 0.0483(11) 0.0574(12) 0.0298(8) -0.0011(10) 0.0141(7) 0.0042(8) N1 0.0255(10) 0.0302(10) 0.0266(9) -0.0028(9) 0.0053(7) -0.0043(8) N2 0.0253(9) 0.0357(10) 0.0276(9) -0.0014(9) 0.0043(7) -0.0037(8) C3 0.0294(11) 0.0297(11) 0.0285(11) 0.0046(10) 0.0054(9) 0.0016(9) C4 0.0405(14) 0.0275(12) 0.0382(12) 0.0018(11) 0.0112(10) 0.0009(10) C5 0.0336(12) 0.0322(12) 0.0303(11) -0.0049(11) 0.0065(9) -0.0037(10) C6 0.0351(12) 0.0312(12) 0.0218(10) -0.0038(10) 0.0086(9) -0.0028(9) C7 0.0285(12) 0.0338(13) 0.0302(11) -0.0026(10) 0.0069(9) -0.0033(10) C8 0.0238(11) 0.0306(11) 0.0302(11) -0.0039(10) 0.0045(8) -0.0031(10) C9 0.0253(11) 0.0286(11) 0.0354(12) 0.0012(10) 0.0055(9) -0.0011(10) C10 0.0246(11) 0.0268(11) 0.0301(11) -0.0012(10) 0.0014(8) 0.0002(9) C11 0.0343(12) 0.0287(11) 0.0353(12) -0.0002(11) 0.0008(9) 0.0026(10) C12 0.0392(13) 0.0376(13) 0.0311(12) -0.0053(12) 0.0025(10) 0.0054(10) C13 0.0300(12) 0.0434(14) 0.0275(10) -0.0077(11) 0.0056(8) -0.0020(10) C14 0.0271(11) 0.0360(13) 0.0287(10) -0.0014(11) 0.0033(8) -0.0024(10) C15 0.0227(10) 0.0280(11) 0.0287(10) -0.0019(10) 0.0019(8) -0.0029(9) C16 0.0285(11) 0.0302(11) 0.0298(11) 0.0029(10) 0.0038(9) -0.0002(10) C17 0.0304(11) 0.0299(12) 0.0295(11) 0.0005(10) 0.0041(9) 0.0004(9) C18 0.0533(17) 0.072(2) 0.0350(13) 0.0065(16) 0.0182(11) -0.0027(14) C19 0.0380(13) 0.0512(15) 0.0297(11) -0.0006(12) 0.0042(10) 0.0001(12) C20 0.0235(11) 0.0340(12) 0.0270(10) -0.0038(10) 0.0041(8) -0.0008(9) C21 0.0395(13) 0.0335(12) 0.0343(11) 0.0007(11) 0.0064(10) 0.0042(10) C22 0.0486(16) 0.0537(16) 0.0390(13) -0.0066(14) 0.0011(11) 0.0162(13) C23 0.0439(15) 0.090(3) 0.0304(12) -0.0106(17) 0.0080(11) 0.0117(15) C24 0.0410(15) 0.092(3) 0.0333(14) 0.0060(16) 0.0134(11) -0.0032(15) C25 0.0317(12) 0.0581(17) 0.0351(13) 0.0104(12) 0.0059(10) -0.0010(12) #============================================================================== _computing_data_collection 'CrystalClear-SM Expert 2.0 rc13 (Rigaku, 2009)' _computing_cell_refinement 'CrystalClear-SM Expert 2.0 rc13' _computing_data_reduction 'CrystalClear-SM Expert 2.0 rc13' _computing_structure_solution 'SIR2004 (Burla, et al., 2005)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 O5 C5 1.213(3) yes . . O6 C6 1.215(3) yes . . O13 C13 1.373(3) yes . . O13 C18 1.426(4) yes . . N1 N2 1.441(3) yes . . N1 C5 1.400(3) yes . . N1 C6 1.399(3) yes . . N2 C3 1.490(3) yes . . C3 C4 1.523(4) yes . . C3 C20 1.520(4) yes . . C4 C5 1.496(4) yes . . C6 C7 1.518(3) yes . . C7 C8 1.526(4) yes . . C7 C19 1.534(3) yes . . C8 C9 1.373(4) yes . . C8 C17 1.415(4) yes . . C9 C10 1.420(4) yes . . C10 C11 1.420(4) yes . . C10 C15 1.419(4) yes . . C11 C12 1.367(4) yes . . C12 C13 1.417(4) yes . . C13 C14 1.368(4) yes . . C14 C15 1.433(4) yes . . C15 C16 1.412(3) yes . . C16 C17 1.377(4) yes . . C20 C21 1.389(4) yes . . C20 C25 1.381(4) yes . . C21 C22 1.387(4) yes . . C22 C23 1.381(5) yes . . C23 C24 1.378(5) yes . . C24 C25 1.388(4) yes . . N2 H2 0.977(14) no . . C3 H3 1.000 no . . C4 H4A 0.990 no . . C4 H4B 0.990 no . . C7 H7 1.000 no . . C9 H9 0.950 no . . C11 H11 0.950 no . . C12 H12 0.950 no . . C14 H14 0.950 no . . C16 H16 0.950 no . . C17 H17 0.950 no . . C18 H18A 0.980 no . . C18 H18B 0.980 no . . C18 H18C 0.980 no . . C19 H19A 0.980 no . . C19 H19B 0.980 no . . C19 H19C 0.980 no . . C21 H21 0.950 no . . C22 H22 0.950 no . . C23 H23 0.950 no . . C24 H24 0.950 no . . C25 H25 0.950 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C13 O13 C18 116.9(2) yes . . . N2 N1 C5 112.41(17) yes . . . N2 N1 C6 116.80(17) yes . . . C5 N1 C6 129.96(19) yes . . . N1 N2 C3 104.11(16) yes . . . N2 C3 C4 104.80(19) yes . . . N2 C3 C20 112.59(19) yes . . . C4 C3 C20 111.73(18) yes . . . C3 C4 C5 103.38(19) yes . . . O5 C5 N1 125.9(2) yes . . . O5 C5 C4 127.2(3) yes . . . N1 C5 C4 106.84(18) yes . . . O6 C6 N1 119.0(2) yes . . . O6 C6 C7 123.7(2) yes . . . N1 C6 C7 117.32(18) yes . . . C6 C7 C8 111.26(16) yes . . . C6 C7 C19 107.46(18) yes . . . C8 C7 C19 115.16(19) yes . . . C7 C8 C9 118.5(2) yes . . . C7 C8 C17 122.9(2) yes . . . C9 C8 C17 118.5(2) yes . . . C8 C9 C10 121.9(2) yes . . . C9 C10 C11 122.0(2) yes . . . C9 C10 C15 119.0(2) yes . . . C11 C10 C15 119.0(2) yes . . . C10 C11 C12 120.6(3) yes . . . C11 C12 C13 120.6(3) yes . . . O13 C13 C12 113.9(2) yes . . . O13 C13 C14 125.5(3) yes . . . C12 C13 C14 120.6(3) yes . . . C13 C14 C15 119.9(3) yes . . . C10 C15 C14 119.3(2) yes . . . C10 C15 C16 118.5(2) yes . . . C14 C15 C16 122.2(2) yes . . . C15 C16 C17 121.0(2) yes . . . C8 C17 C16 121.1(2) yes . . . C3 C20 C21 123.0(2) yes . . . C3 C20 C25 118.4(2) yes . . . C21 C20 C25 118.6(3) yes . . . C20 C21 C22 120.4(3) yes . . . C21 C22 C23 120.3(3) yes . . . C22 C23 C24 119.9(3) yes . . . C23 C24 C25 119.6(3) yes . . . C20 C25 C24 121.2(3) yes . . . N1 N2 H2 102.9(17) no . . . C3 N2 H2 106.7(17) no . . . N2 C3 H3 109.200 no . . . C4 C3 H3 109.199 no . . . C20 C3 H3 109.200 no . . . C3 C4 H4A 111.091 no . . . C3 C4 H4B 111.080 no . . . C5 C4 H4A 111.086 no . . . C5 C4 H4B 111.088 no . . . H4A C4 H4B 109.052 no . . . C6 C7 H7 107.549 no . . . C8 C7 H7 107.555 no . . . C19 C7 H7 107.552 no . . . C8 C9 H9 119.046 no . . . C10 C9 H9 119.041 no . . . C10 C11 H11 119.713 no . . . C12 C11 H11 119.723 no . . . C11 C12 H12 119.696 no . . . C13 C12 H12 119.696 no . . . C13 C14 H14 120.037 no . . . C15 C14 H14 120.037 no . . . C15 C16 H16 119.497 no . . . C17 C16 H16 119.497 no . . . C8 C17 H17 119.471 no . . . C16 C17 H17 119.465 no . . . O13 C18 H18A 109.471 no . . . O13 C18 H18B 109.469 no . . . O13 C18 H18C 109.475 no . . . H18A C18 H18B 109.471 no . . . H18A C18 H18C 109.476 no . . . H18B C18 H18C 109.466 no . . . C7 C19 H19A 109.474 no . . . C7 C19 H19B 109.469 no . . . C7 C19 H19C 109.476 no . . . H19A C19 H19B 109.467 no . . . H19A C19 H19C 109.476 no . . . H19B C19 H19C 109.465 no . . . C20 C21 H21 119.800 no . . . C22 C21 H21 119.803 no . . . C21 C22 H22 119.868 no . . . C23 C22 H22 119.872 no . . . C22 C23 H23 120.061 no . . . C24 C23 H23 120.056 no . . . C23 C24 H24 120.191 no . . . C25 C24 H24 120.188 no . . . C20 C25 H25 119.388 no . . . C24 C25 H25 119.392 no . . . 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C18 O13 C13 C12 -179.17(18) no . . . . C18 O13 C13 C14 0.3(3) no . . . . N2 N1 C5 O5 173.94(18) no . . . . N2 N1 C5 C4 -3.6(2) no . . . . C5 N1 N2 C3 -14.8(2) no . . . . N2 N1 C6 O6 2.5(3) no . . . . N2 N1 C6 C7 -176.27(15) no . . . . C6 N1 N2 C3 174.56(15) no . . . . C5 N1 C6 O6 -166.18(18) no . . . . C5 N1 C6 C7 15.1(3) no . . . . C6 N1 C5 O5 -17.0(4) no . . . . C6 N1 C5 C4 165.47(17) no . . . . N1 N2 C3 C4 26.62(18) no . . . . N1 N2 C3 C20 -95.03(18) no . . . . N2 C3 C4 C5 -28.7(2) no . . . . N2 C3 C20 C21 15.1(3) no . . . . N2 C3 C20 C25 -165.94(15) no . . . . C4 C3 C20 C21 -102.6(3) no . . . . C4 C3 C20 C25 76.4(3) no . . . . C20 C3 C4 C5 93.5(2) no . . . . C3 C4 C5 O5 -157.5(2) no . . . . C3 C4 C5 N1 20.0(2) no . . . . O6 C6 C7 C8 39.0(3) no . . . . O6 C6 C7 C19 -87.9(3) no . . . . N1 C6 C7 C8 -142.33(17) no . . . . N1 C6 C7 C19 90.8(2) no . . . . C6 C7 C8 C9 80.3(3) no . . . . C6 C7 C8 C17 -102.1(2) no . . . . C19 C7 C8 C9 -157.11(18) no . . . . C19 C7 C8 C17 20.5(3) no . . . . C7 C8 C9 C10 177.08(16) no . . . . C7 C8 C17 C16 -176.24(17) no . . . . C9 C8 C17 C16 1.4(3) no . . . . C17 C8 C9 C10 -0.7(3) no . . . . C8 C9 C10 C11 179.70(17) no . . . . C8 C9 C10 C15 -0.5(3) no . . . . C9 C10 C11 C12 179.34(18) no . . . . C9 C10 C15 C14 -178.95(16) no . . . . C9 C10 C15 C16 1.0(3) no . . . . C11 C10 C15 C14 0.8(3) no . . . . C11 C10 C15 C16 -179.20(17) no . . . . C15 C10 C11 C12 -0.4(3) no . . . . C10 C11 C12 C13 0.2(4) no . . . . C11 C12 C13 O13 179.04(19) no . . . . C11 C12 C13 C14 -0.4(4) no . . . . O13 C13 C14 C15 -178.57(18) no . . . . C12 C13 C14 C15 0.8(3) no . . . . C13 C14 C15 C10 -1.0(3) no . . . . C13 C14 C15 C16 178.99(18) no . . . . C10 C15 C16 C17 -0.3(3) no . . . . C14 C15 C16 C17 179.65(17) no . . . . C15 C16 C17 C8 -0.9(3) no . . . . C3 C20 C21 C22 -179.77(17) no . . . . C3 C20 C25 C24 179.38(18) no . . . . C21 C20 C25 C24 -1.6(4) no . . . . C25 C20 C21 C22 1.2(3) no . . . . C20 C21 C22 C23 -0.3(4) no . . . . C21 C22 C23 C24 -0.4(4) no . . . . C22 C23 C24 C25 0.1(4) no . . . . C23 C24 C25 C20 0.9(4) no . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 O5 N2 3.525(3) no . . O5 C3 3.527(4) no . . O5 C6 3.027(3) no . . O5 C7 2.883(3) no . . O5 C19 3.478(4) no . . O6 N2 2.647(3) no . . O6 C5 3.582(3) no . . O6 C8 2.888(3) no . . O6 C9 3.589(4) no . . O6 C17 3.531(4) no . . O6 C19 3.176(3) no . . N1 C19 3.255(4) no . . N1 C20 3.185(4) no . . N1 C21 3.325(4) no . . N2 C21 2.875(4) no . . C4 C21 3.485(4) no . . C4 C25 3.191(4) no . . C5 C7 3.024(4) no . . C5 C20 3.206(4) no . . C6 C9 3.217(4) no . . C6 C17 3.495(4) no . . C8 C15 2.835(4) no . . C9 C16 2.782(4) no . . C10 C13 2.810(4) no . . C10 C17 2.800(4) no . . C11 C14 2.809(4) no . . C12 C15 2.804(4) no . . C14 C18 2.817(4) no . . C17 C19 2.990(4) no . . C20 C23 2.786(4) no . . C21 C24 2.766(4) no . . C22 C25 2.752(5) no . . O5 O6 3.558(3) no . 1_565 O5 C18 3.574(4) no . 2_755 O5 C19 3.374(4) no . 1_565 O5 C23 3.436(4) no . 2_656 O6 O5 3.558(3) no . 1_545 O6 N1 3.223(3) no . 2_645 O6 N2 2.977(3) no . 2_645 O6 C3 3.531(4) no . 2_645 O6 C4 3.574(4) no . 1_545 O6 C4 3.495(4) no . 2_645 O6 C5 3.580(3) no . 2_645 O13 C18 3.427(4) no . 2_754 N1 O6 3.223(3) no . 2_655 N2 O6 2.977(3) no . 2_655 C3 O6 3.531(4) no . 2_655 C4 O6 3.574(4) no . 1_565 C4 O6 3.495(4) no . 2_655 C5 O6 3.580(3) no . 2_655 C10 C16 3.494(3) no . 2_755 C15 C16 3.598(3) no . 2_755 C16 C10 3.494(3) no . 2_745 C16 C15 3.598(3) no . 2_745 C18 O5 3.574(4) no . 2_745 C18 O13 3.427(4) no . 2_744 C19 O5 3.374(4) no . 1_545 C23 O5 3.436(4) no . 2_646 O5 H4A 2.8749 no . . O5 H4B 2.6595 no . . O5 H7 2.1135 no . . O5 H19B 3.0891 no . . O6 H7 3.1487 no . . O6 H17 3.5792 no . . O6 H19A 2.9884 no . . O6 H19B 3.4752 no . . O6 H2 2.70(3) no . . O13 H12 2.4811 no . . O13 H14 2.6573 no . . N1 H3 3.1105 no . . N1 H4A 2.8543 no . . N1 H4B 3.1024 no . . N1 H7 2.5217 no . . N1 H19B 3.0130 no . . N1 H21 2.8143 no . . N2 H4A 2.8389 no . . N2 H4B 3.2075 no . . N2 H21 2.5344 no . . C3 H21 2.7263 no . . C3 H25 2.6204 no . . C4 H25 3.1153 no . . C4 H2 2.71(3) no . . C5 H3 3.1799 no . . C5 H7 2.5608 no . . C5 H19B 3.3195 no . . C5 H21 3.4170 no . . C5 H2 2.77(3) no . . C6 H9 3.1479 no . . C6 H19A 2.6470 no . . C6 H19B 2.6355 no . . C6 H19C 3.3149 no . . C6 H21 3.4669 no . . C6 H2 2.66(3) no . . C7 H9 2.6149 no . . C7 H17 2.7511 no . . C8 H16 3.2851 no . . C8 H19A 2.8170 no . . C8 H19B 3.4070 no . . C8 H19C 2.7639 no . . C9 H7 2.5893 no . . C9 H11 2.6703 no . . C9 H17 3.2524 no . . C10 H12 3.2776 no . . C10 H14 3.3192 no . . C10 H16 3.2922 no . . C11 H9 2.6602 no . . C12 H14 3.2777 no . . C13 H11 3.2754 no . . C13 H18A 2.6211 no . . C13 H18B 2.6163 no . . C13 H18C 3.2019 no . . C14 H12 3.2685 no . . C14 H16 2.6712 no . . C14 H18A 2.7573 no . . C14 H18B 2.7452 no . . C15 H9 3.3004 no . . C15 H11 3.3042 no . . C15 H17 3.2810 no . . C16 H14 2.6869 no . . C17 H7 3.2883 no . . C17 H9 3.2562 no . . C17 H19A 2.8485 no . . C17 H19C 2.9828 no . . C18 H14 2.5208 no . . C19 H17 2.6684 no . . C20 H4A 3.3171 no . . C20 H4B 2.5413 no . . C20 H22 3.2645 no . . C20 H24 3.2674 no . . C20 H2 3.286(15) no . . C21 H3 3.2608 no . . C21 H4B 3.5384 no . . C21 H23 3.2575 no . . C21 H25 3.2410 no . . C22 H24 3.2473 no . . C23 H21 3.2551 no . . C23 H25 3.2456 no . . C24 H22 3.2451 no . . C25 H3 2.6474 no . . C25 H4B 2.8539 no . . C25 H21 3.2425 no . . C25 H23 3.2511 no . . H3 H4A 2.2490 no . . H3 H4B 2.6037 no . . H3 H21 3.5219 no . . H3 H25 2.5011 no . . H3 H2 2.1751 no . . H4A H25 3.5527 no . . H4A H2 2.8170 no . . H4B H25 2.7278 no . . H7 H9 2.4182 no . . H7 H17 3.5687 no . . H7 H19A 2.8628 no . . H7 H19B 2.3366 no . . H7 H19C 2.3785 no . . H9 H11 2.4965 no . . H11 H12 2.3084 no . . H14 H16 2.5194 no . . H14 H18A 2.3243 no . . H14 H18B 2.2928 no . . H14 H18C 3.4922 no . . H16 H17 2.3124 no . . H17 H19A 2.2808 no . . H17 H19C 2.6652 no . . H19B H21 3.5098 no . . H21 H22 2.3323 no . . H21 H2 3.4925 no . . H22 H23 2.3297 no . . H23 H24 2.3320 no . . H24 H25 2.3321 no . . O5 H18B 2.6642 no . 2_755 O5 H19A 2.4759 no . 1_565 O5 H19B 3.5218 no . 1_565 O5 H23 2.5065 no . 2_656 O6 H3 3.4014 no . 2_645 O6 H4A 2.8599 no . 1_545 O6 H4A 2.9875 no . 2_645 O6 H2 2.09(3) no . 2_645 O13 H18A 2.9894 no . 2_754 O13 H18C 2.9591 no . 2_754 O13 H19A 3.3385 no . 2_755 O13 H19C 3.1026 no . 2_755 O13 H24 3.5563 no . 2_645 N2 H4A 3.3399 no . 1_545 N2 H9 3.1464 no . 2_645 N2 H11 3.2706 no . 2_645 C3 H11 3.0998 no . 2_645 C4 H21 3.0957 no . 1_565 C4 H23 3.4305 no . 2_656 C5 H19A 3.4879 no . 1_565 C5 H23 3.0443 no . 2_656 C6 H4A 3.5800 no . 1_545 C6 H4A 3.4124 no . 2_645 C6 H2 3.18(3) no . 2_645 C7 H14 3.3880 no . 2_755 C7 H18B 3.3793 no . 2_755 C8 H3 3.0113 no . 2_645 C8 H4A 3.5738 no . 2_645 C8 H14 3.5050 no . 2_755 C8 H16 3.1272 no . 2_755 C8 H2 3.48(3) no . 2_645 C9 H3 2.8665 no . 2_645 C9 H4A 3.0945 no . 2_645 C9 H16 3.1063 no . 2_755 C10 H3 2.7379 no . 2_645 C10 H4A 3.5278 no . 2_645 C10 H16 3.4992 no . 1_565 C10 H16 3.0570 no . 2_755 C10 H17 3.5208 no . 2_755 C10 H25 3.2046 no . 2_645 C11 H3 3.5611 no . 2_645 C11 H16 3.0643 no . 1_565 C11 H25 3.0598 no . 2_645 C12 H14 3.5448 no . 1_565 C12 H18C 3.3784 no . 2_754 C12 H19C 3.0433 no . 2_755 C12 H25 2.9115 no . 2_645 C13 H17 3.2922 no . 2_755 C13 H19A 3.4565 no . 2_755 C13 H19C 3.0943 no . 2_755 C13 H25 2.9022 no . 2_645 C14 H17 3.0571 no . 2_755 C14 H25 3.0498 no . 2_645 C15 H3 2.7573 no . 2_645 C15 H11 3.5132 no . 1_545 C15 H16 2.9988 no . 2_755 C15 H17 3.1857 no . 2_755 C15 H25 3.1900 no . 2_645 C16 H3 2.8765 no . 2_645 C16 H11 3.0733 no . 1_545 C16 H16 3.0065 no . 2_755 C17 H3 2.9894 no . 2_645 C17 H9 3.5091 no . 1_545 C17 H16 3.0769 no . 2_755 C17 H2 3.47(3) no . 2_645 C18 H12 3.5591 no . 2_744 C18 H18A 3.5049 no . 2_754 C18 H19B 3.4641 no . 2_745 C18 H19C 3.2567 no . 2_745 C18 H23 3.3622 no . 1_654 C19 H14 3.3895 no . 2_755 C19 H18A 3.5292 no . 2_755 C19 H18B 3.1093 no . 2_755 C19 H24 3.5277 no . 2_646 C20 H11 2.8350 no . 2_645 C20 H22 3.3258 no . 2_656 C21 H4B 3.0553 no . 1_545 C21 H11 3.1346 no . 2_645 C21 H22 3.1120 no . 2_656 C22 H4B 3.4143 no . 1_545 C22 H22 2.9706 no . 2_656 C23 H4B 3.3206 no . 2_646 C23 H12 3.4226 no . 2_645 C23 H18C 3.1975 no . 1_456 C23 H22 3.0462 no . 2_656 C24 H12 3.3286 no . 2_645 C24 H18C 3.3797 no . 1_456 C24 H19B 3.5662 no . 2_656 C24 H22 3.2423 no . 2_656 C25 H11 3.3039 no . 2_645 C25 H12 3.5294 no . 2_645 C25 H22 3.3603 no . 2_656 H3 O6 3.4014 no . 2_655 H3 C8 3.0113 no . 2_655 H3 C9 2.8665 no . 2_655 H3 C10 2.7379 no . 2_655 H3 C11 3.5611 no . 2_655 H3 C15 2.7573 no . 2_655 H3 C16 2.8765 no . 2_655 H3 C17 2.9894 no . 2_655 H3 H9 3.4269 no . 2_655 H3 H11 2.8441 no . 2_645 H3 H16 3.4441 no . 2_655 H3 H17 3.5930 no . 2_655 H4A O6 2.8599 no . 1_565 H4A O6 2.9875 no . 2_655 H4A N2 3.3399 no . 1_565 H4A C6 3.5800 no . 1_565 H4A C6 3.4124 no . 2_655 H4A C8 3.5738 no . 2_655 H4A C9 3.0945 no . 2_655 H4A C10 3.5278 no . 2_655 H4A H9 2.9933 no . 2_655 H4A H21 2.9724 no . 1_565 H4B C21 3.0553 no . 1_565 H4B C22 3.4143 no . 1_565 H4B C23 3.3206 no . 2_656 H4B H21 2.3744 no . 1_565 H4B H22 3.0884 no . 1_565 H4B H22 3.4891 no . 2_656 H4B H23 2.8760 no . 2_656 H7 H14 2.9252 no . 2_755 H7 H17 3.5002 no . 1_565 H7 H18B 2.7086 no . 2_755 H7 H19A 3.5405 no . 1_565 H9 N2 3.1464 no . 2_655 H9 C17 3.5091 no . 1_565 H9 H3 3.4269 no . 2_645 H9 H4A 2.9933 no . 2_645 H9 H16 3.3910 no . 1_565 H9 H17 3.1064 no . 1_565 H9 H2 2.9587 no . 2_655 H11 N2 3.2706 no . 2_655 H11 C3 3.0998 no . 2_655 H11 C15 3.5132 no . 1_565 H11 C16 3.0733 no . 1_565 H11 C20 2.8350 no . 2_655 H11 C21 3.1346 no . 2_655 H11 C25 3.3039 no . 2_655 H11 H3 2.8441 no . 2_655 H11 H14 3.4593 no . 1_565 H11 H16 2.7659 no . 1_565 H11 H21 3.3879 no . 2_655 H11 H25 3.5978 no . 2_645 H11 H2 3.5966 no . 2_655 H12 C18 3.5591 no . 2_754 H12 C23 3.4226 no . 2_655 H12 C24 3.3286 no . 2_655 H12 C25 3.5294 no . 2_655 H12 H14 3.1642 no . 1_565 H12 H18A 2.9863 no . 1_565 H12 H18C 2.6229 no . 2_754 H12 H19C 2.9743 no . 2_755 H12 H25 3.3857 no . 2_645 H14 C7 3.3880 no . 2_745 H14 C8 3.5050 no . 2_745 H14 C12 3.5448 no . 1_545 H14 C19 3.3895 no . 2_745 H14 H7 2.9252 no . 2_745 H14 H11 3.4593 no . 1_545 H14 H12 3.1642 no . 1_545 H14 H17 3.3673 no . 2_755 H14 H19C 2.6733 no . 2_745 H14 H25 3.5907 no . 2_645 H16 C8 3.1272 no . 2_745 H16 C9 3.1063 no . 2_745 H16 C10 3.4992 no . 1_545 H16 C10 3.0570 no . 2_745 H16 C11 3.0643 no . 1_545 H16 C15 2.9988 no . 2_745 H16 C16 3.0065 no . 2_745 H16 C17 3.0769 no . 2_745 H16 H3 3.4441 no . 2_645 H16 H9 3.3910 no . 1_545 H16 H11 2.7659 no . 1_545 H16 H16 3.5165 no . 2_745 H16 H16 3.5165 no . 2_755 H17 C10 3.5208 no . 2_745 H17 C13 3.2922 no . 2_745 H17 C14 3.0571 no . 2_745 H17 C15 3.1857 no . 2_745 H17 H3 3.5930 no . 2_645 H17 H7 3.5002 no . 1_545 H17 H9 3.1064 no . 1_545 H17 H14 3.3673 no . 2_745 H17 H2 3.5628 no . 2_645 H18A O13 2.9894 no . 2_744 H18A C18 3.5049 no . 2_744 H18A C19 3.5292 no . 2_745 H18A H12 2.9863 no . 1_545 H18A H18C 3.0350 no . 2_744 H18A H19B 3.3792 no . 2_745 H18A H19C 2.8441 no . 2_745 H18A H24 3.2791 no . 2_645 H18B O5 2.6642 no . 2_745 H18B C7 3.3793 no . 2_745 H18B C19 3.1093 no . 2_745 H18B H7 2.7086 no . 2_745 H18B H19A 3.0408 no . 2_755 H18B H19B 2.8358 no . 2_745 H18B H19C 2.7818 no . 2_745 H18B H23 2.9901 no . 1_654 H18C O13 2.9591 no . 2_744 H18C C12 3.3784 no . 2_744 H18C C23 3.1975 no . 1_654 H18C C24 3.3797 no . 1_654 H18C H12 2.6229 no . 2_744 H18C H18A 3.0350 no . 2_754 H18C H23 2.8586 no . 1_654 H18C H24 3.1956 no . 1_654 H19A O5 2.4759 no . 1_545 H19A O13 3.3385 no . 2_745 H19A C5 3.4879 no . 1_545 H19A C13 3.4565 no . 2_745 H19A H7 3.5405 no . 1_545 H19A H18B 3.0408 no . 2_745 H19A H23 3.5602 no . 2_646 H19A H24 3.5970 no . 2_646 H19B O5 3.5218 no . 1_545 H19B C18 3.4641 no . 2_755 H19B C24 3.5662 no . 2_646 H19B H18A 3.3792 no . 2_755 H19B H18B 2.8358 no . 2_755 H19B H24 2.7924 no . 2_646 H19C O13 3.1026 no . 2_745 H19C C12 3.0433 no . 2_745 H19C C13 3.0943 no . 2_745 H19C C18 3.2567 no . 2_755 H19C H12 2.9743 no . 2_745 H19C H14 2.6733 no . 2_755 H19C H18A 2.8441 no . 2_755 H19C H18B 2.7818 no . 2_755 H21 C4 3.0957 no . 1_545 H21 H4A 2.9724 no . 1_545 H21 H4B 2.3744 no . 1_545 H21 H11 3.3879 no . 2_645 H21 H22 3.5898 no . 2_656 H22 C20 3.3258 no . 2_646 H22 C21 3.1120 no . 2_646 H22 C22 2.9706 no . 2_646 H22 C23 3.0462 no . 2_646 H22 C24 3.2423 no . 2_646 H22 C25 3.3603 no . 2_646 H22 H4B 3.0884 no . 1_545 H22 H4B 3.4891 no . 2_646 H22 H21 3.5898 no . 2_646 H22 H22 3.3854 no . 2_646 H22 H22 3.3854 no . 2_656 H22 H23 3.5019 no . 2_646 H22 H25 3.3795 no . 1_545 H23 O5 2.5065 no . 2_646 H23 C4 3.4305 no . 2_646 H23 C5 3.0443 no . 2_646 H23 C18 3.3622 no . 1_456 H23 H4B 2.8760 no . 2_646 H23 H18B 2.9901 no . 1_456 H23 H18C 2.8586 no . 1_456 H23 H19A 3.5602 no . 2_656 H23 H22 3.5019 no . 2_656 H24 O13 3.5563 no . 2_655 H24 C19 3.5277 no . 2_656 H24 H18A 3.2791 no . 2_655 H24 H18C 3.1956 no . 1_456 H24 H19A 3.5970 no . 2_656 H24 H19B 2.7924 no . 2_656 H25 C10 3.2046 no . 2_655 H25 C11 3.0598 no . 2_655 H25 C12 2.9115 no . 2_655 H25 C13 2.9022 no . 2_655 H25 C14 3.0498 no . 2_655 H25 C15 3.1900 no . 2_655 H25 H11 3.5978 no . 2_655 H25 H12 3.3857 no . 2_655 H25 H14 3.5907 no . 2_655 H25 H22 3.3795 no . 1_565 H2 O6 2.09(3) no . 2_655 H2 C6 3.18(3) no . 2_655 H2 C8 3.48(3) no . 2_655 H2 C17 3.47(3) no . 2_655 H2 H9 2.9587 no . 2_645 H2 H11 3.5966 no . 2_645 H2 H17 3.5628 no . 2_655 #============================================================================== loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_distance_DA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_angle_DHA _geom_hbond_publ_flag N2 H2 O6 . . 2_655 2.977(3) 0.977 2.094(14) 149(3) no #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #============================================================================== _database_code_depnum_ccdc_archive 'CCDC 956166' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_17 _chemical_formula_sum 'C24 H24 N2 O3' _chemical_formula_moiety 'C24 H24 N2 O3' _chemical_formula_weight 388.47 _chemical_melting_point ? _chemical_absolute_configuration syn #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2 1' _symmetry_space_group_name_Hall 'C 2y' _symmetry_Int_Tables_number 5 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,+Y,-Z 3 1/2+X,1/2+Y,+Z 4 1/2-X,1/2+Y,-Z #------------------------------------------------------------------------------ _cell_length_a 19.58(2) _cell_length_b 5.868(5) _cell_length_c 19.289(17) _cell_angle_alpha 90.0000 _cell_angle_beta 111.93(3) _cell_angle_gamma 90.0000 _cell_volume 2055(4) _cell_formula_units_Z 4 _cell_measurement_reflns_used 790 _cell_measurement_theta_min 21.30 _cell_measurement_theta_max 68.25 _cell_measurement_temperature 173 #------------------------------------------------------------------------------ _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.020 _exptl_crystal_size_min 0.020 _exptl_crystal_density_diffrn 1.255 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824.00 _exptl_absorpt_coefficient_mu 0.669 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'REQAB (Rigaku, 1998)' _exptl_absorpt_correction_T_min 0.766 _exptl_absorpt_correction_T_max 0.987 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 173 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54187 _diffrn_measurement_device_type 'Rigaku Saturn70' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 29.257 _diffrn_reflns_number 8029 _diffrn_reflns_av_R_equivalents 0.0931 _diffrn_reflns_theta_min 2.469 _diffrn_reflns_theta_max 68.566 _diffrn_reflns_theta_full 83.500 _diffrn_measured_fraction_theta_max 0.799 _diffrn_measured_fraction_theta_full 0.659 _diffrn_reflns_Laue_measured_fraction_max 0.799 _diffrn_reflns_Laue_measured_fraction_full 0.659 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 22 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 2707 _reflns_number_gt 1943 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0759 _refine_ls_wR_factor_ref 0.2055 _refine_ls_number_restraints 1 _refine_ls_hydrogen_treatment mixed _refine_ls_number_reflns 2707 _refine_ls_number_parameters 266 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.1156P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_diff_density_max 0.220 _refine_diff_density_min -0.310 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Parsons and Flack (2004), Acta Cryst. A60, s61' _refine_ls_abs_structure_Flack 0.4(4) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.0311 0.0180 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.0492 0.0322 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 O5 O 0.7873(3) -0.0066(9) 0.8695(3) 0.0543(15) Uani 1.0 4 d . . . O6 O 0.6512(3) 0.5722(10) 0.8131(3) 0.0641(16) Uani 1.0 4 d . . . O13 O 0.9180(3) 0.2875(11) 0.5221(3) 0.0683(18) Uani 1.0 4 d . . . N1 N 0.7500(3) 0.3654(10) 0.8770(3) 0.0436(15) Uani 1.0 4 d . . . N2 N 0.7686(3) 0.5373(11) 0.9345(4) 0.0506(17) Uani 1.0 4 d . . . C3 C 0.8475(4) 0.4931(12) 0.9792(4) 0.0473(19) Uani 1.0 4 d . . . C4 C 0.8534(4) 0.2367(12) 0.9752(4) 0.051(2) Uani 1.0 4 d . . . C5 C 0.7947(4) 0.1777(13) 0.9021(5) 0.047(2) Uani 1.0 4 d . . . C6 C 0.6844(4) 0.3946(15) 0.8163(4) 0.049(2) Uani 1.0 4 d . . . C7 C 0.6599(4) 0.2163(14) 0.7553(5) 0.054(2) Uani 1.0 4 d . . . C8 C 0.7028(4) 0.2585(13) 0.7047(4) 0.048(2) Uani 1.0 4 d . . . C9 C 0.7531(4) 0.1077(14) 0.6980(4) 0.052(2) Uani 1.0 4 d . . . C10 C 0.7937(4) 0.1502(13) 0.6524(5) 0.052(3) Uani 1.0 4 d . . . C11 C 0.8481(5) 0.0017(14) 0.6463(5) 0.056(2) Uani 1.0 4 d . . . C12 C 0.8869(4) 0.0550(16) 0.6035(5) 0.060(3) Uani 1.0 4 d . . . C13 C 0.8749(5) 0.2575(16) 0.5624(5) 0.058(3) Uani 1.0 4 d . . . C14 C 0.8216(4) 0.4061(15) 0.5653(5) 0.058(3) Uani 1.0 4 d . . . C15 C 0.7814(4) 0.3560(15) 0.6110(4) 0.053(2) Uani 1.0 4 d . . . C16 C 0.7278(4) 0.5086(14) 0.6165(5) 0.057(3) Uani 1.0 4 d . . . C17 C 0.6902(5) 0.4617(14) 0.6623(5) 0.058(3) Uani 1.0 4 d . . . C18 C 0.8667(4) 0.5886(13) 1.0571(4) 0.052(2) Uani 1.0 4 d . . . C19 C 0.5767(4) 0.2266(17) 0.7135(5) 0.066(3) Uani 1.0 4 d . . . C20 C 0.9066(5) 0.485(2) 0.4764(5) 0.084(3) Uani 1.0 4 d . . . C21 C 0.9477(4) 0.5698(13) 1.1051(4) 0.0458(19) Uani 1.0 4 d . . . C22 C 0.9964(5) 0.7431(14) 1.1079(5) 0.053(2) Uani 1.0 4 d . . . C23 C 1.0697(5) 0.7285(15) 1.1515(5) 0.059(3) Uani 1.0 4 d . . . C24 C 1.0969(5) 0.5324(15) 1.1922(5) 0.060(3) Uani 1.0 4 d . . . C25 C 1.0495(5) 0.3573(16) 1.1910(5) 0.068(3) Uani 1.0 4 d . . . C26 C 0.9765(5) 0.3765(15) 1.1482(5) 0.061(3) Uani 1.0 4 d . . . H2 H 0.767(5) 0.685(16) 0.901(5) 0.08(3) Uiso 1.0 4 d . . . H3 H 0.8788 0.5672 0.9549 0.0567 Uiso 1.0 4 calc R . . H4A H 0.9025 0.1910 0.9765 0.0612 Uiso 1.0 4 calc R . . H4B H 0.8444 0.1618 1.0170 0.0612 Uiso 1.0 4 calc R . . H7 H 0.6732 0.0623 0.7786 0.0651 Uiso 1.0 4 calc R . . H9 H 0.7611 -0.0312 0.7252 0.0621 Uiso 1.0 4 calc R . . H11 H 0.8576 -0.1385 0.6729 0.0675 Uiso 1.0 4 calc R . . H12 H 0.9235 -0.0480 0.6012 0.0717 Uiso 1.0 4 calc R . . H14 H 0.8119 0.5423 0.5366 0.0694 Uiso 1.0 4 calc R . . H16 H 0.7176 0.6454 0.5881 0.0687 Uiso 1.0 4 calc R . . H17 H 0.6549 0.5680 0.6655 0.0697 Uiso 1.0 4 calc R . . H18A H 0.8521 0.7510 1.0532 0.0621 Uiso 1.0 4 calc R . . H18B H 0.8379 0.5064 1.0819 0.0621 Uiso 1.0 4 calc R . . H19A H 0.5629 0.3769 0.6903 0.0794 Uiso 1.0 4 calc R . . H19B H 0.5520 0.2007 0.7486 0.0794 Uiso 1.0 4 calc R . . H19C H 0.5616 0.1087 0.6747 0.0794 Uiso 1.0 4 calc R . . H20A H 0.9142 0.6214 0.5075 0.1014 Uiso 1.0 4 calc R . . H20B H 0.8561 0.4840 0.4391 0.1014 Uiso 1.0 4 calc R . . H20C H 0.9415 0.4844 0.4509 0.1014 Uiso 1.0 4 calc R . . H22 H 0.9785 0.8763 1.0788 0.0641 Uiso 1.0 4 calc R . . H23 H 1.1017 0.8525 1.1538 0.0714 Uiso 1.0 4 calc R . . H24 H 1.1481 0.5183 1.2208 0.0721 Uiso 1.0 4 calc R . . H25 H 1.0677 0.2239 1.2199 0.0815 Uiso 1.0 4 calc R . . H26 H 0.9442 0.2549 1.1477 0.0734 Uiso 1.0 4 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O5 0.073(4) 0.038(3) 0.051(4) 0.006(3) 0.021(3) -0.005(3) O6 0.064(4) 0.062(4) 0.057(4) 0.024(4) 0.012(3) 0.001(3) O13 0.064(4) 0.091(5) 0.054(4) -0.002(4) 0.026(4) 0.009(4) N1 0.050(4) 0.037(3) 0.036(4) 0.008(3) 0.007(3) -0.002(3) N2 0.058(4) 0.041(4) 0.045(4) 0.005(3) 0.010(4) 0.001(3) C3 0.059(5) 0.040(5) 0.042(5) 0.002(4) 0.018(4) 0.004(4) C4 0.061(5) 0.035(5) 0.047(5) 0.004(4) 0.009(5) -0.001(4) C5 0.052(5) 0.045(5) 0.048(5) 0.005(4) 0.022(4) 0.003(4) C6 0.052(5) 0.055(5) 0.043(5) 0.011(4) 0.021(4) 0.002(4) C7 0.060(5) 0.051(5) 0.052(5) -0.001(4) 0.021(5) -0.006(4) C8 0.054(5) 0.050(5) 0.036(5) 0.000(4) 0.012(4) 0.002(4) C9 0.059(5) 0.050(5) 0.039(5) 0.004(4) 0.010(4) 0.005(4) C10 0.059(5) 0.051(5) 0.045(5) -0.003(4) 0.017(5) 0.003(4) C11 0.059(5) 0.054(5) 0.049(5) 0.007(4) 0.012(5) -0.000(5) C12 0.055(5) 0.073(6) 0.048(5) 0.007(5) 0.016(5) 0.001(5) C13 0.053(5) 0.072(6) 0.045(5) -0.010(5) 0.011(5) -0.002(5) C14 0.050(5) 0.066(6) 0.051(5) -0.002(4) 0.012(5) 0.003(5) C15 0.053(5) 0.056(5) 0.041(5) 0.003(4) 0.007(4) -0.002(4) C16 0.062(5) 0.054(5) 0.049(5) 0.001(5) 0.013(5) 0.010(4) C17 0.061(5) 0.055(5) 0.059(6) 0.007(4) 0.022(5) 0.008(5) C18 0.068(5) 0.040(5) 0.051(5) -0.005(4) 0.026(5) -0.005(4) C19 0.056(5) 0.081(6) 0.054(5) -0.006(5) 0.012(5) -0.007(5) C20 0.076(6) 0.112(9) 0.064(6) -0.010(6) 0.024(5) 0.009(7) C21 0.056(5) 0.042(5) 0.042(5) -0.004(4) 0.021(4) -0.005(4) C22 0.065(6) 0.046(5) 0.048(5) -0.009(4) 0.020(5) -0.001(4) C23 0.065(6) 0.059(6) 0.056(5) -0.011(5) 0.025(5) -0.014(5) C24 0.060(5) 0.060(6) 0.053(6) 0.007(5) 0.012(5) -0.009(5) C25 0.073(6) 0.052(5) 0.061(6) 0.001(5) 0.005(5) 0.004(5) C26 0.078(6) 0.044(5) 0.052(5) -0.011(5) 0.014(5) 0.004(5) #============================================================================== _computing_data_collection 'CrystalClear-SM Expert 2.0 r2 (Rigaku, 2009)' _computing_cell_refinement 'CrystalClear-SM Expert 2.0 r2' _computing_data_reduction 'CrystalClear-SM Expert 2.0 r2' _computing_structure_solution 'SIR2004 (Burla, et al., 2005)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 O5 C5 1.232(9) yes . . O6 C6 1.217(10) yes . . O13 C13 1.355(12) yes . . O13 C20 1.421(13) yes . . N1 N2 1.441(9) yes . . N1 C5 1.378(9) yes . . N1 C6 1.389(8) yes . . N2 C3 1.484(9) yes . . C3 C4 1.513(10) yes . . C3 C18 1.512(11) yes . . C4 C5 1.489(10) yes . . C6 C7 1.512(11) yes . . C7 C8 1.526(14) yes . . C7 C19 1.526(10) yes . . C8 C9 1.365(12) yes . . C8 C17 1.415(11) yes . . C9 C10 1.410(13) yes . . C10 C11 1.415(12) yes . . C10 C15 1.418(12) yes . . C11 C12 1.353(14) yes . . C12 C13 1.398(13) yes . . C13 C14 1.376(13) yes . . C14 C15 1.414(14) yes . . C15 C16 1.414(12) yes . . C16 C17 1.371(14) yes . . C18 C21 1.513(9) yes . . C21 C22 1.380(11) yes . . C21 C26 1.395(11) yes . . C22 C23 1.369(11) yes . . C23 C24 1.382(12) yes . . C24 C25 1.379(13) yes . . C25 C26 1.364(11) yes . . N2 H2 1.07(10) no . . C3 H3 1.000 no . . C4 H4A 0.990 no . . C4 H4B 0.990 no . . C7 H7 1.000 no . . C9 H9 0.950 no . . C11 H11 0.950 no . . C12 H12 0.950 no . . C14 H14 0.950 no . . C16 H16 0.950 no . . C17 H17 0.950 no . . C18 H18A 0.990 no . . C18 H18B 0.990 no . . C19 H19A 0.980 no . . C19 H19B 0.980 no . . C19 H19C 0.980 no . . C20 H20A 0.980 no . . C20 H20B 0.980 no . . C20 H20C 0.980 no . . C22 H22 0.950 no . . C23 H23 0.950 no . . C24 H24 0.950 no . . C25 H25 0.950 no . . C26 H26 0.950 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C13 O13 C20 118.4(7) yes . . . N2 N1 C5 110.2(5) yes . . . N2 N1 C6 116.8(6) yes . . . C5 N1 C6 131.4(6) yes . . . N1 N2 C3 103.6(6) yes . . . N2 C3 C4 103.0(6) yes . . . N2 C3 C18 109.4(7) yes . . . C4 C3 C18 115.1(6) yes . . . C3 C4 C5 103.5(6) yes . . . O5 C5 N1 125.7(6) yes . . . O5 C5 C4 126.2(7) yes . . . N1 C5 C4 108.1(6) yes . . . O6 C6 N1 117.1(7) yes . . . O6 C6 C7 123.0(6) yes . . . N1 C6 C7 119.7(7) yes . . . C6 C7 C8 107.2(7) yes . . . C6 C7 C19 110.4(8) yes . . . C8 C7 C19 113.0(7) yes . . . C7 C8 C9 123.0(7) yes . . . C7 C8 C17 119.2(8) yes . . . C9 C8 C17 117.9(9) yes . . . C8 C9 C10 122.6(8) yes . . . C9 C10 C11 124.0(8) yes . . . C9 C10 C15 119.0(8) yes . . . C11 C10 C15 116.9(8) yes . . . C10 C11 C12 121.4(8) yes . . . C11 C12 C13 121.9(9) yes . . . O13 C13 C12 115.2(8) yes . . . O13 C13 C14 125.8(8) yes . . . C12 C13 C14 119.0(9) yes . . . C13 C14 C15 120.0(8) yes . . . C10 C15 C14 120.7(8) yes . . . C10 C15 C16 118.1(9) yes . . . C14 C15 C16 121.2(8) yes . . . C15 C16 C17 120.9(8) yes . . . C8 C17 C16 121.5(8) yes . . . C3 C18 C21 113.3(7) yes . . . C18 C21 C22 121.4(7) yes . . . C18 C21 C26 121.4(7) yes . . . C22 C21 C26 117.2(7) yes . . . C21 C22 C23 121.9(7) yes . . . C22 C23 C24 119.6(8) yes . . . C23 C24 C25 119.8(7) yes . . . C24 C25 C26 119.7(8) yes . . . C21 C26 C25 121.7(9) yes . . . N1 N2 H2 100(5) no . . . C3 N2 H2 106(5) no . . . N2 C3 H3 109.694 no . . . C4 C3 H3 109.692 no . . . C18 C3 H3 109.686 no . . . C3 C4 H4A 111.055 no . . . C3 C4 H4B 111.058 no . . . C5 C4 H4A 111.055 no . . . C5 C4 H4B 111.057 no . . . H4A C4 H4B 109.031 no . . . C6 C7 H7 108.733 no . . . C8 C7 H7 108.732 no . . . C19 C7 H7 108.734 no . . . C8 C9 H9 118.698 no . . . C10 C9 H9 118.698 no . . . C10 C11 H11 119.325 no . . . C12 C11 H11 119.318 no . . . C11 C12 H12 119.042 no . . . C13 C12 H12 119.038 no . . . C13 C14 H14 119.983 no . . . C15 C14 H14 119.987 no . . . C15 C16 H16 119.564 no . . . C17 C16 H16 119.536 no . . . C8 C17 H17 119.274 no . . . C16 C17 H17 119.268 no . . . C3 C18 H18A 108.916 no . . . C3 C18 H18B 108.910 no . . . C21 C18 H18A 108.916 no . . . C21 C18 H18B 108.920 no . . . H18A C18 H18B 107.742 no . . . C7 C19 H19A 109.475 no . . . C7 C19 H19B 109.471 no . . . C7 C19 H19C 109.479 no . . . H19A C19 H19B 109.461 no . . . H19A C19 H19C 109.475 no . . . H19B C19 H19C 109.467 no . . . O13 C20 H20A 109.475 no . . . O13 C20 H20B 109.470 no . . . O13 C20 H20C 109.472 no . . . H20A C20 H20B 109.478 no . . . H20A C20 H20C 109.468 no . . . H20B C20 H20C 109.464 no . . . C21 C22 H22 119.058 no . . . C23 C22 H22 119.057 no . . . C22 C23 H23 120.205 no . . . C24 C23 H23 120.205 no . . . C23 C24 H24 120.106 no . . . C25 C24 H24 120.106 no . . . C24 C25 H25 120.132 no . . . C26 C25 H25 120.135 no . . . C21 C26 H26 119.124 no . . . C25 C26 H26 119.139 no . . . 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C20 O13 C13 C12 177.2(6) no . . . . C20 O13 C13 C14 -2.3(10) no . . . . N2 N1 C5 O5 171.5(8) no . . . . N2 N1 C5 C4 -8.6(9) no . . . . C5 N1 N2 C3 27.1(8) no . . . . N2 N1 C6 O6 6.4(11) no . . . . N2 N1 C6 C7 -177.8(6) no . . . . C6 N1 N2 C3 -165.7(6) no . . . . C5 N1 C6 O6 170.3(8) no . . . . C5 N1 C6 C7 -13.9(13) no . . . . C6 N1 C5 O5 6.7(15) no . . . . C6 N1 C5 C4 -173.3(8) no . . . . N1 N2 C3 C4 -33.8(7) no . . . . N1 N2 C3 C18 -156.7(5) no . . . . N2 C3 C4 C5 28.8(8) no . . . . N2 C3 C18 C21 -175.1(6) no . . . . C4 C3 C18 C21 69.5(9) no . . . . C18 C3 C4 C5 147.8(7) no . . . . C3 C4 C5 O5 166.8(8) no . . . . C3 C4 C5 N1 -13.2(9) no . . . . O6 C6 C7 C8 95.6(9) no . . . . O6 C6 C7 C19 -27.8(12) no . . . . N1 C6 C7 C8 -80.0(9) no . . . . N1 C6 C7 C19 156.6(7) no . . . . C6 C7 C8 C9 114.4(7) no . . . . C6 C7 C8 C17 -65.9(7) no . . . . C19 C7 C8 C9 -123.7(7) no . . . . C19 C7 C8 C17 55.9(9) no . . . . C7 C8 C9 C10 -178.6(6) no . . . . C7 C8 C17 C16 179.5(6) no . . . . C9 C8 C17 C16 -0.9(10) no . . . . C17 C8 C9 C10 1.7(10) no . . . . C8 C9 C10 C11 177.5(6) no . . . . C8 C9 C10 C15 -0.7(10) no . . . . C9 C10 C11 C12 -177.8(6) no . . . . C9 C10 C15 C14 179.2(6) no . . . . C9 C10 C15 C16 -1.1(9) no . . . . C11 C10 C15 C14 0.8(9) no . . . . C11 C10 C15 C16 -179.5(6) no . . . . C15 C10 C11 C12 0.5(10) no . . . . C10 C11 C12 C13 -0.7(11) no . . . . C11 C12 C13 O13 180.0(6) no . . . . C11 C12 C13 C14 -0.4(11) no . . . . O13 C13 C14 C15 -178.7(6) no . . . . C12 C13 C14 C15 1.7(11) no . . . . C13 C14 C15 C10 -2.0(10) no . . . . C13 C14 C15 C16 178.3(6) no . . . . C10 C15 C16 C17 1.9(10) no . . . . C14 C15 C16 C17 -178.4(6) no . . . . C15 C16 C17 C8 -0.9(11) no . . . . C3 C18 C21 C22 91.4(8) no . . . . C3 C18 C21 C26 -88.5(9) no . . . . C18 C21 C22 C23 179.6(7) no . . . . C18 C21 C26 C25 179.3(7) no . . . . C22 C21 C26 C25 -0.5(13) no . . . . C26 C21 C22 C23 -0.5(13) no . . . . C21 C22 C23 C24 2.2(14) no . . . . C22 C23 C24 C25 -2.8(14) no . . . . C23 C24 C25 C26 1.7(14) no . . . . C24 C25 C26 C21 -0.0(14) no . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 O5 N2 3.497(9) no . . O5 C3 3.551(9) no . . O5 C6 3.018(10) no . . O5 C7 2.946(9) no . . O5 C8 3.365(9) no . . O5 C9 3.191(10) no . . O6 N2 2.605(7) no . . O6 C5 3.549(9) no . . O6 C8 3.218(11) no . . O6 C17 3.336(12) no . . O6 C19 2.800(10) no . . O13 C11 3.588(12) no . . N1 C8 3.162(10) no . . C3 C6 3.594(10) no . . C3 C22 3.377(10) no . . C3 C26 3.363(10) no . . C4 C21 3.171(10) no . . C4 C26 3.407(10) no . . C5 C7 3.075(10) no . . C5 C8 3.583(11) no . . C6 C9 3.484(13) no . . C6 C17 3.041(13) no . . C8 C15 2.836(13) no . . C9 C16 2.769(12) no . . C10 C13 2.828(14) no . . C10 C17 2.787(12) no . . C11 C14 2.782(12) no . . C12 C15 2.762(13) no . . C14 C20 2.837(15) no . . C17 C19 3.076(14) no . . C21 C24 2.781(10) no . . C22 C25 2.744(12) no . . C23 C26 2.742(13) no . . O5 O6 3.496(8) no . 1_545 O5 N2 3.035(9) no . 1_545 O5 C3 3.554(9) no . 1_545 O5 C23 3.356(12) no . 2_747 O6 O5 3.496(8) no . 1_565 O6 C26 3.374(12) no . 4_657 O13 C16 3.503(9) no . 4_646 N1 C18 3.412(11) no . 4_647 N2 O5 3.035(9) no . 1_565 C3 O5 3.554(9) no . 1_565 C5 C18 3.569(13) no . 4_647 C6 C18 3.466(13) no . 4_647 C13 C16 3.592(11) no . 4_646 C16 O13 3.503(9) no . 4_656 C16 C13 3.592(11) no . 4_656 C18 N1 3.412(11) no . 4_657 C18 C5 3.569(13) no . 4_657 C18 C6 3.466(13) no . 4_657 C20 C20 3.424(14) no . 2_756 C23 O5 3.356(12) no . 2_767 C26 O6 3.374(12) no . 4_647 O5 H4A 2.6864 no . . O5 H4B 2.8192 no . . O5 H7 2.3012 no . . O5 H9 2.6392 no . . O6 H2 2.36(8) no . . O6 H7 3.1299 no . . O6 H17 2.8743 no . . O6 H19A 2.6181 no . . O6 H19B 2.8752 no . . O13 H12 2.4684 no . . O13 H14 2.6569 no . . N1 H3 2.6812 no . . N1 H4A 3.0600 no . . N1 H4B 2.8989 no . . N1 H7 2.6255 no . . N2 H4A 3.1730 no . . N2 H4B 2.7973 no . . N2 H18A 2.5871 no . . N2 H18B 2.6606 no . . C3 H22 3.4112 no . . C3 H26 3.3910 no . . C4 H2 3.17(9) no . . C4 H18A 3.3766 no . . C4 H18B 2.7010 no . . C4 H26 3.1346 no . . C5 H2 3.03(9) no . . C5 H3 2.7783 no . . C5 H7 2.7491 no . . C5 H9 3.4505 no . . C6 H2 2.50(8) no . . C6 H17 2.9277 no . . C6 H19A 2.6930 no . . C6 H19B 2.6804 no . . C6 H19C 3.3388 no . . C7 H9 2.6888 no . . C7 H17 2.6719 no . . C8 H16 3.2833 no . . C8 H19A 2.7367 no . . C8 H19B 3.3790 no . . C8 H19C 2.7491 no . . C9 H7 2.5979 no . . C9 H11 2.6912 no . . C9 H17 3.2376 no . . C10 H12 3.2646 no . . C10 H14 3.3168 no . . C10 H16 3.2896 no . . C11 H9 2.6801 no . . C12 H14 3.2525 no . . C13 H11 3.2555 no . . C13 H20A 2.6233 no . . C13 H20B 2.6271 no . . C13 H20C 3.1932 no . . C14 H12 3.2436 no . . C14 H16 2.6432 no . . C14 H20A 2.7625 no . . C14 H20B 2.7958 no . . C15 H9 3.2902 no . . C15 H11 3.2771 no . . C15 H17 3.2758 no . . C16 H14 2.6498 no . . C17 H7 3.3464 no . . C17 H9 3.2415 no . . C17 H19A 2.7843 no . . C17 H19C 3.3375 no . . C18 H2 2.96(8) no . . C18 H4A 3.0272 no . . C18 H4B 2.6093 no . . C18 H22 2.6693 no . . C18 H26 2.6853 no . . C19 H17 2.8766 no . . C20 H14 2.5515 no . . C21 H3 2.7013 no . . C21 H4A 3.1996 no . . C21 H4B 3.1852 no . . C21 H23 3.2564 no . . C21 H25 3.2644 no . . C22 H3 3.1629 no . . C22 H18A 2.6210 no . . C22 H18B 3.2615 no . . C22 H24 3.2360 no . . C22 H26 3.2283 no . . C23 H25 3.2477 no . . C24 H22 3.2316 no . . C24 H26 3.2262 no . . C25 H23 3.2475 no . . C26 H4A 3.2661 no . . C26 H4B 3.1285 no . . C26 H18A 3.2839 no . . C26 H18B 2.6417 no . . C26 H22 3.2300 no . . C26 H24 3.2296 no . . H2 H3 2.1591 no . . H2 H18A 2.8021 no . . H2 H18B 3.3964 no . . H3 H4A 2.2623 no . . H3 H4B 2.8553 no . . H3 H18A 2.4031 no . . H3 H18B 2.8694 no . . H3 H22 3.0539 no . . H4A H18B 3.3280 no . . H4A H26 3.1144 no . . H4B H18A 3.5193 no . . H4B H18B 2.4060 no . . H4B H26 2.6064 no . . H7 H9 2.3765 no . . H7 H19A 2.8679 no . . H7 H19B 2.3669 no . . H7 H19C 2.3662 no . . H9 H11 2.5295 no . . H11 H12 2.2790 no . . H14 H16 2.4763 no . . H14 H20A 2.3199 no . . H14 H20B 2.3709 no . . H14 H20C 3.5247 no . . H16 H17 2.3035 no . . H17 H19A 2.3174 no . . H17 H19C 3.2978 no . . H18A H22 2.4479 no . . H18A H26 3.5491 no . . H18B H22 3.5217 no . . H18B H26 2.4790 no . . H22 H23 2.3085 no . . H23 H24 2.3371 no . . H24 H25 2.3322 no . . H25 H26 2.3031 no . . O5 H2 2.00(10) no . 1_545 O5 H3 3.1580 no . 1_545 O5 H18A 3.5825 no . 1_545 O5 H18B 2.9349 no . 4_647 O5 H23 2.5170 no . 2_747 O6 H4B 3.2885 no . 4_657 O6 H7 3.0184 no . 1_565 O6 H18A 3.2144 no . 4_647 O6 H18B 3.2121 no . 4_657 O6 H26 2.5034 no . 4_657 O13 H16 2.8362 no . 4_646 O13 H17 3.5969 no . 4_646 O13 H20C 2.8465 no . 2_756 N1 H18A 2.8743 no . 4_647 N1 H18B 3.0078 no . 4_647 N1 H24 3.3405 no . 2_757 N2 H4B 2.8023 no . 4_657 N2 H18A 2.9800 no . 4_647 N2 H18B 3.3967 no . 4_657 C4 H18A 3.2271 no . 1_545 C4 H22 3.2873 no . 1_545 C5 H2 2.94(9) no . 1_545 C5 H18A 3.3226 no . 4_647 C5 H18B 2.9071 no . 4_647 C5 H23 3.2474 no . 2_747 C5 H24 3.5846 no . 2_757 C6 H18A 2.9830 no . 4_647 C6 H18B 3.1429 no . 4_647 C6 H26 3.5490 no . 4_657 C7 H18B 3.3597 no . 4_647 C8 H20B 3.0390 no . 4_646 C8 H24 3.1260 no . 2_757 C9 H16 3.3518 no . 1_545 C9 H20B 2.8064 no . 4_646 C9 H23 3.5240 no . 2_747 C9 H24 3.1198 no . 2_757 C9 H25 3.3350 no . 2_757 C10 H14 3.5126 no . 4_646 C10 H16 3.3389 no . 1_545 C10 H20B 2.9670 no . 4_646 C10 H24 3.1410 no . 2_757 C10 H25 2.9366 no . 2_757 C11 H14 3.3355 no . 1_545 C11 H16 3.1649 no . 1_545 C11 H25 2.8101 no . 2_757 C12 H14 3.3850 no . 1_545 C12 H16 3.5325 no . 4_646 C12 H19A 3.3852 no . 3_545 C12 H20A 3.3049 no . 1_545 C12 H25 3.3346 no . 2_757 C13 H16 2.8662 no . 4_646 C14 H11 3.2950 no . 1_565 C14 H14 3.3792 no . 4_646 C14 H16 3.1612 no . 4_646 C15 H11 3.3344 no . 1_565 C15 H14 3.3093 no . 4_646 C15 H20B 3.3182 no . 4_646 C15 H24 3.1610 no . 2_757 C15 H25 3.5729 no . 2_757 C16 H9 3.3297 no . 1_565 C16 H11 3.1412 no . 1_565 C16 H20B 3.4655 no . 4_646 C16 H20B 3.2116 no . 4_656 C16 H24 3.1716 no . 2_757 C17 H9 3.3154 no . 1_565 C17 H20B 3.3442 no . 4_646 C17 H20B 3.5657 no . 4_656 C17 H24 3.1436 no . 2_757 C18 H4B 3.4422 no . 1_565 C18 H7 3.5400 no . 4_657 C18 H19B 3.5438 no . 4_657 C19 H12 3.2532 no . 3_455 C19 H20C 3.3693 no . 4_646 C20 H12 3.5821 no . 1_565 C20 H16 3.0263 no . 4_646 C20 H17 3.5293 no . 4_646 C20 H19C 3.2806 no . 4_656 C20 H20A 3.4981 no . 2_756 C20 H20C 2.7743 no . 2_756 C21 H19B 2.9227 no . 4_657 C22 H3 3.2730 no . 2_757 C22 H19B 3.2513 no . 4_657 C22 H25 3.5101 no . 1_565 C22 H26 3.3517 no . 1_565 C23 H3 2.7690 no . 2_757 C23 H9 3.5676 no . 2_767 C23 H11 3.2402 no . 2_767 C23 H19B 3.5835 no . 4_657 C23 H25 3.1980 no . 1_565 C24 H3 3.0526 no . 2_757 C24 H11 3.0922 no . 2_767 C25 H19B 3.3313 no . 4_657 C25 H22 3.5122 no . 1_545 C25 H23 3.2985 no . 1_545 C26 H19B 2.9532 no . 4_657 C26 H22 3.2317 no . 1_545 H2 O5 2.00(10) no . 1_565 H2 C5 2.94(9) no . 1_565 H2 H4B 3.5438 no . 1_565 H2 H4B 3.1291 no . 4_657 H2 H7 3.2584 no . 1_565 H2 H18B 2.8894 no . 4_657 H2 H23 3.2816 no . 2_757 H2 H24 3.4972 no . 2_757 H3 O5 3.1580 no . 1_565 H3 C22 3.2730 no . 2_757 H3 C23 2.7690 no . 2_757 H3 C24 3.0526 no . 2_757 H3 H22 3.5882 no . 2_757 H3 H23 2.8176 no . 2_757 H3 H24 3.2419 no . 2_757 H4A H4A 3.5781 no . 2_757 H4A H18A 3.3049 no . 1_545 H4A H22 2.7065 no . 1_545 H4A H22 3.4400 no . 2_747 H4A H23 3.1804 no . 2_747 H4B O6 3.2885 no . 4_647 H4B N2 2.8023 no . 4_647 H4B C18 3.4422 no . 1_545 H4B H2 3.5438 no . 1_545 H4B H2 3.1291 no . 4_647 H4B H18A 2.4983 no . 1_545 H4B H18B 3.4820 no . 4_647 H4B H22 2.9628 no . 1_545 H7 O6 3.0184 no . 1_545 H7 C18 3.5400 no . 4_647 H7 H2 3.2584 no . 1_545 H7 H17 3.5655 no . 1_545 H7 H18B 2.7992 no . 4_647 H9 C16 3.3297 no . 1_545 H9 C17 3.3154 no . 1_545 H9 C23 3.5676 no . 2_747 H9 H16 3.1031 no . 1_545 H9 H17 3.0637 no . 1_545 H9 H20B 3.1444 no . 4_646 H9 H23 2.9056 no . 2_747 H9 H24 3.1382 no . 2_747 H9 H25 3.4550 no . 2_757 H11 C14 3.2950 no . 1_545 H11 C15 3.3344 no . 1_545 H11 C16 3.1412 no . 1_545 H11 C23 3.2402 no . 2_747 H11 C24 3.0922 no . 2_747 H11 H14 3.0766 no . 1_545 H11 H16 2.9065 no . 1_545 H11 H23 3.1328 no . 2_747 H11 H24 2.9051 no . 2_747 H11 H25 2.9450 no . 2_757 H12 C19 3.2532 no . 3_545 H12 C20 3.5821 no . 1_545 H12 H14 3.1731 no . 1_545 H12 H19A 2.6643 no . 3_545 H12 H19B 3.3537 no . 3_545 H12 H19C 3.2424 no . 3_545 H12 H20A 2.6106 no . 1_545 H14 C10 3.5126 no . 4_656 H14 C11 3.3355 no . 1_565 H14 C12 3.3850 no . 1_565 H14 C14 3.3792 no . 4_656 H14 C15 3.3093 no . 4_656 H14 H11 3.0766 no . 1_565 H14 H12 3.1731 no . 1_565 H14 H16 3.2422 no . 4_646 H16 O13 2.8362 no . 4_656 H16 C9 3.3518 no . 1_565 H16 C10 3.3389 no . 1_565 H16 C11 3.1649 no . 1_565 H16 C12 3.5325 no . 4_656 H16 C13 2.8662 no . 4_656 H16 C14 3.1612 no . 4_656 H16 C20 3.0263 no . 4_656 H16 H9 3.1031 no . 1_565 H16 H11 2.9065 no . 1_565 H16 H14 3.2422 no . 4_656 H16 H20B 2.3957 no . 4_656 H16 H20C 3.5317 no . 4_656 H17 O13 3.5969 no . 4_656 H17 C20 3.5293 no . 4_656 H17 H7 3.5655 no . 1_565 H17 H9 3.0637 no . 1_565 H17 H20B 3.1230 no . 4_656 H17 H20C 3.3781 no . 4_656 H18A O5 3.5825 no . 1_565 H18A O6 3.2144 no . 4_657 H18A N1 2.8743 no . 4_657 H18A N2 2.9800 no . 4_657 H18A C4 3.2271 no . 1_565 H18A C5 3.3226 no . 4_657 H18A C6 2.9830 no . 4_657 H18A H4A 3.3049 no . 1_565 H18A H4B 2.4983 no . 1_565 H18A H19B 3.5869 no . 4_657 H18A H26 3.5864 no . 1_565 H18B O5 2.9349 no . 4_657 H18B O6 3.2121 no . 4_647 H18B N1 3.0078 no . 4_657 H18B N2 3.3967 no . 4_647 H18B C5 2.9071 no . 4_657 H18B C6 3.1429 no . 4_657 H18B C7 3.3597 no . 4_657 H18B H2 2.8894 no . 4_647 H18B H4B 3.4820 no . 4_657 H18B H7 2.7992 no . 4_657 H18B H19B 3.3720 no . 4_657 H19A C12 3.3852 no . 3_455 H19A H12 2.6643 no . 3_455 H19A H20C 3.5420 no . 4_646 H19B C18 3.5438 no . 4_647 H19B C21 2.9227 no . 4_647 H19B C22 3.2513 no . 4_647 H19B C23 3.5835 no . 4_647 H19B C25 3.3313 no . 4_647 H19B C26 2.9532 no . 4_647 H19B H12 3.3537 no . 3_455 H19B H18A 3.5869 no . 4_647 H19B H18B 3.3720 no . 4_647 H19B H26 3.2771 no . 4_647 H19C C20 3.2806 no . 4_646 H19C H12 3.2424 no . 3_455 H19C H20A 3.4321 no . 3_445 H19C H20B 3.2541 no . 4_646 H19C H20C 2.5081 no . 4_646 H20A C12 3.3049 no . 1_565 H20A C20 3.4981 no . 2_756 H20A H12 2.6106 no . 1_565 H20A H19C 3.4321 no . 3_555 H20A H20A 3.4780 no . 2_756 H20A H20C 2.7525 no . 2_756 H20B C8 3.0390 no . 4_656 H20B C9 2.8064 no . 4_656 H20B C10 2.9670 no . 4_656 H20B C15 3.3182 no . 4_656 H20B C16 3.2116 no . 4_646 H20B C16 3.4655 no . 4_656 H20B C17 3.5657 no . 4_646 H20B C17 3.3442 no . 4_656 H20B H9 3.1444 no . 4_656 H20B H16 2.3957 no . 4_646 H20B H17 3.1230 no . 4_646 H20B H19C 3.2541 no . 4_656 H20C O13 2.8465 no . 2_756 H20C C19 3.3693 no . 4_656 H20C C20 2.7743 no . 2_756 H20C H16 3.5317 no . 4_646 H20C H17 3.3781 no . 4_646 H20C H19A 3.5420 no . 4_656 H20C H19C 2.5081 no . 4_656 H20C H20A 2.7525 no . 2_756 H20C H20C 2.3651 no . 2_756 H22 C4 3.2873 no . 1_565 H22 C25 3.5122 no . 1_565 H22 C26 3.2317 no . 1_565 H22 H3 3.5882 no . 2_757 H22 H4A 2.7065 no . 1_565 H22 H4A 3.4400 no . 2_767 H22 H4B 2.9628 no . 1_565 H22 H22 3.4458 no . 2_757 H22 H25 3.3268 no . 1_565 H22 H26 2.7952 no . 1_565 H23 O5 2.5170 no . 2_767 H23 C5 3.2474 no . 2_767 H23 C9 3.5240 no . 2_767 H23 C25 3.2985 no . 1_565 H23 H2 3.2816 no . 2_757 H23 H3 2.8176 no . 2_757 H23 H4A 3.1804 no . 2_767 H23 H9 2.9056 no . 2_767 H23 H11 3.1328 no . 2_767 H23 H25 2.7294 no . 1_565 H24 N1 3.3405 no . 2_757 H24 C5 3.5846 no . 2_757 H24 C8 3.1260 no . 2_757 H24 C9 3.1198 no . 2_757 H24 C10 3.1410 no . 2_757 H24 C15 3.1610 no . 2_757 H24 C16 3.1716 no . 2_757 H24 C17 3.1436 no . 2_757 H24 H2 3.4972 no . 2_757 H24 H3 3.2419 no . 2_757 H24 H9 3.1382 no . 2_767 H24 H11 2.9051 no . 2_767 H25 C9 3.3350 no . 2_757 H25 C10 2.9366 no . 2_757 H25 C11 2.8101 no . 2_757 H25 C12 3.3346 no . 2_757 H25 C15 3.5729 no . 2_757 H25 C22 3.5101 no . 1_545 H25 C23 3.1980 no . 1_545 H25 H9 3.4550 no . 2_757 H25 H11 2.9450 no . 2_757 H25 H22 3.3268 no . 1_545 H25 H23 2.7294 no . 1_545 H26 O6 2.5034 no . 4_647 H26 C6 3.5490 no . 4_647 H26 C22 3.3517 no . 1_545 H26 H18A 3.5864 no . 1_545 H26 H19B 3.2771 no . 4_657 H26 H22 2.7952 no . 1_545 #============================================================================== loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_distance_DA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_angle_DHA _geom_hbond_publ_flag N2 H2 O5 . . 1_565 3.035(9) 1.070 2.00(10) 162(6) no #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #============================================================================== _database_code_depnum_ccdc_archive 'CCDC 956167' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_18 # CHEMICAL DATA _chemical_formula_sum 'C24 H24 N2 O3' _chemical_formula_moiety 'C24 H24 N2 O3' _chemical_formula_weight 388.47 _chemical_melting_point ? _chemical_absolute_configuration syn #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21 1' _symmetry_space_group_name_Hall 'P 2yb' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,1/2+Y,-Z #------------------------------------------------------------------------------ _cell_length_a 10.185(7) _cell_length_b 8.422(5) _cell_length_c 12.404(8) _cell_angle_alpha 90.0000 _cell_angle_beta 111.547(12) _cell_angle_gamma 90.0000 _cell_volume 989.6(11) _cell_formula_units_Z 2 _cell_measurement_reflns_used 1103 _cell_measurement_theta_min 21.49 _cell_measurement_theta_max 68.25 _cell_measurement_temperature 173 #------------------------------------------------------------------------------ _exptl_crystal_description platelet _exptl_crystal_colour colorless _exptl_crystal_size_max 0.100 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.020 _exptl_crystal_density_diffrn 1.304 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 412.00 _exptl_absorpt_coefficient_mu 0.695 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'REQAB (Rigaku, 1998)' _exptl_absorpt_correction_T_min 0.687 _exptl_absorpt_correction_T_max 0.986 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 173 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54187 _diffrn_measurement_device_type 'Rigaku Saturn70' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 29.257 _diffrn_reflns_number 12943 _diffrn_reflns_av_R_equivalents 0.1062 _diffrn_reflns_theta_min 3.832 _diffrn_reflns_theta_max 68.223 _diffrn_reflns_theta_full 68.500 _diffrn_measured_fraction_theta_max 0.992 _diffrn_measured_fraction_theta_full 0.988 _diffrn_reflns_Laue_measured_fraction_max 0.992 _diffrn_reflns_Laue_measured_fraction_full 0.988 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 3485 _reflns_number_gt 3004 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0613 _refine_ls_wR_factor_ref 0.1758 _refine_ls_number_restraints 2 _refine_ls_hydrogen_treatment mixed _refine_ls_number_reflns 3485 _refine_ls_number_parameters 266 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0936P)^2^+0.2390P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_diff_density_max 0.220 _refine_diff_density_min -0.250 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Parsons and Flack (2004), Acta Cryst. A60, s61.' _refine_ls_abs_structure_Flack 0.4(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.0311 0.0180 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.0492 0.0322 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 O5 O 0.3777(4) 0.2311(5) 0.8970(3) 0.0532(10) Uani 1.0 2 d . . . O6 O 0.5731(4) 0.2296(5) 1.1325(3) 0.0509(9) Uani 1.0 2 d . . . O13 O 0.9624(4) -0.0373(5) 0.5715(3) 0.0531(9) Uani 1.0 2 d . . . N1 N 0.5887(4) 0.3683(5) 0.9811(3) 0.0373(9) Uani 1.0 2 d . . . N2 N 0.6806(4) 0.4612(5) 0.9426(3) 0.0380(9) Uani 1.0 2 d . . . C3 C 0.6374(5) 0.4225(6) 0.8177(4) 0.0386(10) Uani 1.0 2 d . . . C4 C 0.4811(5) 0.3853(6) 0.7799(4) 0.0412(11) Uani 1.0 2 d . . . C5 C 0.4688(5) 0.3182(6) 0.8884(4) 0.0414(11) Uani 1.0 2 d . . . C6 C 0.6479(5) 0.2789(6) 1.0835(4) 0.0390(11) Uani 1.0 2 d . . . C7 C 0.8046(5) 0.2402(6) 1.1207(4) 0.0382(10) Uani 1.0 2 d . . . C8 C 0.8261(5) 0.1566(6) 1.0197(4) 0.0368(10) Uani 1.0 2 d . . . C9 C 0.9326(5) 0.1978(6) 0.9828(4) 0.0370(10) Uani 1.0 2 d . . . C10 C 0.9438(5) 0.1307(6) 0.8809(4) 0.0338(10) Uani 1.0 2 d . . . C11 C 1.0523(5) 0.1744(6) 0.8419(4) 0.0402(11) Uani 1.0 2 d . . . C12 C 1.0551(5) 0.1135(6) 0.7400(4) 0.0413(11) Uani 1.0 2 d . . . C13 C 0.9480(5) 0.0090(6) 0.6725(4) 0.0414(11) Uani 1.0 2 d . . . C14 C 0.8443(5) -0.0399(6) 0.7098(4) 0.0410(11) Uani 1.0 2 d . . . C15 C 0.8400(5) 0.0197(5) 0.8159(4) 0.0346(10) Uani 1.0 2 d . . . C16 C 0.7346(5) -0.0254(6) 0.8575(4) 0.0389(10) Uani 1.0 2 d . . . C17 C 0.7282(5) 0.0394(6) 0.9569(4) 0.0383(10) Uani 1.0 2 d . . . C18 C 0.6781(6) 0.5579(6) 0.7554(4) 0.0462(12) Uani 1.0 2 d . . . C19 C 0.8560(6) 0.1408(7) 1.2317(4) 0.0492(12) Uani 1.0 2 d . . . C20 C 0.8544(7) -0.1374(9) 0.4974(5) 0.0643(16) Uani 1.0 2 d . . . C21 C 0.6632(6) 0.5170(6) 0.6328(4) 0.0415(11) Uani 1.0 2 d . . . C22 C 0.7591(5) 0.4179(7) 0.6113(4) 0.0467(12) Uani 1.0 2 d . . . C23 C 0.7488(6) 0.3820(8) 0.4999(5) 0.0554(13) Uani 1.0 2 d . . . C24 C 0.6389(6) 0.4460(8) 0.4066(5) 0.0598(15) Uani 1.0 2 d . . . C25 C 0.5424(6) 0.5441(8) 0.4268(5) 0.0575(15) Uani 1.0 2 d . . . C26 C 0.5534(6) 0.5795(6) 0.5392(5) 0.0472(12) Uani 1.0 2 d . . . H2 H 0.647(7) 0.569(3) 0.947(6) 0.08(3) Uiso 1.0 2 d . . . H3 H 0.6883 0.3244 0.8096 0.0463 Uiso 1.0 2 calc R . . H4A H 0.4232 0.4824 0.7543 0.0495 Uiso 1.0 2 calc R . . H4B H 0.4516 0.3065 0.7162 0.0495 Uiso 1.0 2 calc R . . H7 H 0.8588 0.3421 1.1359 0.0458 Uiso 1.0 2 calc R . . H9 H 1.0010 0.2732 1.0262 0.0444 Uiso 1.0 2 calc R . . H11 H 1.1238 0.2462 0.8861 0.0483 Uiso 1.0 2 calc R . . H12 H 1.1294 0.1419 0.7148 0.0495 Uiso 1.0 2 calc R . . H14 H 0.7751 -0.1135 0.6651 0.0493 Uiso 1.0 2 calc R . . H16 H 0.6664 -0.1021 0.8160 0.0466 Uiso 1.0 2 calc R . . H17 H 0.6570 0.0051 0.9840 0.0459 Uiso 1.0 2 calc R . . H18A H 0.6180 0.6510 0.7535 0.0554 Uiso 1.0 2 calc R . . H18B H 0.7773 0.5883 0.7998 0.0554 Uiso 1.0 2 calc R . . H19A H 0.8034 0.0406 1.2183 0.0590 Uiso 1.0 2 calc R . . H19B H 0.8405 0.1997 1.2941 0.0590 Uiso 1.0 2 calc R . . H19C H 0.9569 0.1184 1.2537 0.0590 Uiso 1.0 2 calc R . . H20A H 0.7623 -0.0868 0.4804 0.0772 Uiso 1.0 2 calc R . . H20B H 0.8563 -0.2396 0.5358 0.0772 Uiso 1.0 2 calc R . . H20C H 0.8701 -0.1548 0.4250 0.0772 Uiso 1.0 2 calc R . . H22 H 0.8341 0.3735 0.6748 0.0560 Uiso 1.0 2 calc R . . H23 H 0.8162 0.3141 0.4871 0.0664 Uiso 1.0 2 calc R . . H24 H 0.6304 0.4222 0.3294 0.0717 Uiso 1.0 2 calc R . . H25 H 0.4673 0.5883 0.3632 0.0689 Uiso 1.0 2 calc R . . H26 H 0.4856 0.6466 0.5520 0.0566 Uiso 1.0 2 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O5 0.0399(18) 0.065(3) 0.054(2) -0.0118(18) 0.0159(16) -0.0044(19) O6 0.054(2) 0.058(3) 0.047(2) -0.0027(18) 0.0265(17) 0.0039(16) O13 0.055(2) 0.068(3) 0.0397(18) -0.0002(19) 0.0213(15) -0.0080(18) N1 0.039(2) 0.042(2) 0.0310(18) -0.0037(18) 0.0135(15) -0.0019(17) N2 0.043(3) 0.039(2) 0.0320(18) -0.0056(18) 0.0141(16) -0.0013(17) C3 0.048(3) 0.037(3) 0.032(3) -0.000(2) 0.0158(19) 0.0003(18) C4 0.041(3) 0.045(3) 0.033(3) 0.001(3) 0.0075(18) -0.003(2) C5 0.035(3) 0.046(3) 0.042(3) -0.001(2) 0.011(2) -0.006(2) C6 0.045(3) 0.043(3) 0.032(3) -0.004(2) 0.016(2) -0.0047(19) C7 0.038(3) 0.045(3) 0.031(2) -0.003(2) 0.0119(18) -0.003(2) C8 0.034(3) 0.045(3) 0.029(2) -0.0000(19) 0.0087(18) -0.0021(19) C9 0.035(3) 0.039(3) 0.032(3) 0.0011(19) 0.0076(18) -0.0025(18) C10 0.031(2) 0.038(3) 0.030(2) 0.0007(18) 0.0089(17) 0.0023(18) C11 0.033(3) 0.043(3) 0.041(3) 0.001(2) 0.0087(19) 0.002(2) C12 0.039(3) 0.047(3) 0.038(3) 0.003(3) 0.014(2) 0.006(2) C13 0.044(3) 0.050(3) 0.030(3) 0.007(2) 0.0141(19) 0.0003(19) C14 0.045(3) 0.042(3) 0.035(3) 0.003(2) 0.0127(19) -0.002(2) C15 0.033(3) 0.035(3) 0.034(3) 0.0030(18) 0.0095(18) -0.0018(17) C16 0.039(3) 0.039(3) 0.037(3) -0.001(2) 0.0117(19) -0.004(2) C17 0.038(3) 0.041(3) 0.033(3) -0.001(2) 0.0101(18) 0.0005(19) C18 0.060(3) 0.037(3) 0.040(3) -0.004(3) 0.017(3) -0.001(2) C19 0.051(3) 0.057(3) 0.036(3) 0.001(3) 0.012(3) 0.001(3) C20 0.069(4) 0.082(4) 0.039(3) -0.005(4) 0.017(3) -0.016(3) C21 0.046(3) 0.040(3) 0.037(3) 0.000(2) 0.013(2) 0.005(2) C22 0.043(3) 0.053(3) 0.041(3) 0.005(3) 0.012(2) 0.002(3) C23 0.056(3) 0.064(4) 0.050(3) -0.002(3) 0.023(3) -0.005(3) C24 0.072(4) 0.073(4) 0.039(3) -0.018(4) 0.027(3) -0.002(3) C25 0.060(4) 0.064(4) 0.037(3) -0.014(3) 0.004(3) 0.010(3) C26 0.044(3) 0.047(3) 0.048(3) -0.001(3) 0.013(2) 0.005(3) #============================================================================== _computing_data_collection 'CrystalClear-SM Expert 2.0 r2 (Rigaku, 2009)' _computing_cell_refinement 'CrystalClear-SM Expert 2.0 r2' _computing_data_reduction 'CrystalClear-SM Expert 2.0 r2' _computing_structure_solution 'SIR2004 (Burla, et al., 2005)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 O5 C5 1.217(7) yes . . O6 C6 1.210(7) yes . . O13 C13 1.370(7) yes . . O13 C20 1.422(7) yes . . N1 N2 1.430(6) yes . . N1 C5 1.400(5) yes . . N1 C6 1.407(6) yes . . N2 C3 1.483(6) yes . . C3 C4 1.518(7) yes . . C3 C18 1.518(8) yes . . C4 C5 1.506(8) yes . . C6 C7 1.525(7) yes . . C7 C8 1.521(7) yes . . C7 C19 1.530(7) yes . . C8 C9 1.368(8) yes . . C8 C17 1.416(6) yes . . C9 C10 1.427(7) yes . . C10 C11 1.409(8) yes . . C10 C15 1.420(6) yes . . C11 C12 1.374(8) yes . . C12 C13 1.412(7) yes . . C13 C14 1.363(8) yes . . C14 C15 1.424(7) yes . . C15 C16 1.403(8) yes . . C16 C17 1.372(7) yes . . C18 C21 1.511(8) yes . . C21 C22 1.384(8) yes . . C21 C26 1.386(6) yes . . C22 C23 1.380(8) yes . . C23 C24 1.390(7) yes . . C24 C25 1.376(10) yes . . C25 C26 1.389(8) yes . . N2 H2 0.98(4) no . . C3 H3 1.000 no . . C4 H4A 0.990 no . . C4 H4B 0.990 no . . C7 H7 1.000 no . . C9 H9 0.950 no . . C11 H11 0.950 no . . C12 H12 0.950 no . . C14 H14 0.950 no . . C16 H16 0.950 no . . C17 H17 0.950 no . . C18 H18A 0.990 no . . C18 H18B 0.990 no . . C19 H19A 0.980 no . . C19 H19B 0.980 no . . C19 H19C 0.980 no . . C20 H20A 0.980 no . . C20 H20B 0.980 no . . C20 H20C 0.980 no . . C22 H22 0.950 no . . C23 H23 0.950 no . . C24 H24 0.950 no . . C25 H25 0.950 no . . C26 H26 0.950 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C13 O13 C20 116.3(5) yes . . . N2 N1 C5 111.8(4) yes . . . N2 N1 C6 118.6(4) yes . . . C5 N1 C6 122.4(4) yes . . . N1 N2 C3 104.4(4) yes . . . N2 C3 C4 104.1(5) yes . . . N2 C3 C18 109.6(4) yes . . . C4 C3 C18 116.7(4) yes . . . C3 C4 C5 102.9(4) yes . . . O5 C5 N1 124.9(5) yes . . . O5 C5 C4 128.3(4) yes . . . N1 C5 C4 106.7(4) yes . . . O6 C6 N1 119.8(5) yes . . . O6 C6 C7 123.8(4) yes . . . N1 C6 C7 116.2(5) yes . . . C6 C7 C8 107.5(4) yes . . . C6 C7 C19 111.3(5) yes . . . C8 C7 C19 112.5(4) yes . . . C7 C8 C9 122.0(4) yes . . . C7 C8 C17 119.4(5) yes . . . C9 C8 C17 118.5(5) yes . . . C8 C9 C10 121.8(4) yes . . . C9 C10 C11 121.9(4) yes . . . C9 C10 C15 118.6(5) yes . . . C11 C10 C15 119.4(5) yes . . . C10 C11 C12 120.1(4) yes . . . C11 C12 C13 120.4(5) yes . . . O13 C13 C12 113.7(5) yes . . . O13 C13 C14 125.5(5) yes . . . C12 C13 C14 120.8(5) yes . . . C13 C14 C15 119.9(5) yes . . . C10 C15 C14 119.2(5) yes . . . C10 C15 C16 118.7(5) yes . . . C14 C15 C16 122.1(4) yes . . . C15 C16 C17 121.2(4) yes . . . C8 C17 C16 121.0(5) yes . . . C3 C18 C21 113.3(4) yes . . . C18 C21 C22 121.0(4) yes . . . C18 C21 C26 120.6(5) yes . . . C22 C21 C26 118.4(5) yes . . . C21 C22 C23 121.8(5) yes . . . C22 C23 C24 119.4(6) yes . . . C23 C24 C25 119.5(6) yes . . . C24 C25 C26 120.8(5) yes . . . C21 C26 C25 120.2(6) yes . . . N1 N2 H2 102(5) no . . . C3 N2 H2 107(4) no . . . N2 C3 H3 108.729 no . . . C4 C3 H3 108.732 no . . . C18 C3 H3 108.731 no . . . C3 C4 H4A 111.182 no . . . C3 C4 H4B 111.177 no . . . C5 C4 H4A 111.174 no . . . C5 C4 H4B 111.179 no . . . H4A C4 H4B 109.118 no . . . C6 C7 H7 108.480 no . . . C8 C7 H7 108.471 no . . . C19 C7 H7 108.475 no . . . C8 C9 H9 119.113 no . . . C10 C9 H9 119.093 no . . . C10 C11 H11 119.939 no . . . C12 C11 H11 119.935 no . . . C11 C12 H12 119.794 no . . . C13 C12 H12 119.786 no . . . C13 C14 H14 120.047 no . . . C15 C14 H14 120.055 no . . . C15 C16 H16 119.385 no . . . C17 C16 H16 119.400 no . . . C8 C17 H17 119.484 no . . . C16 C17 H17 119.477 no . . . C3 C18 H18A 108.906 no . . . C3 C18 H18B 108.911 no . . . C21 C18 H18A 108.912 no . . . C21 C18 H18B 108.914 no . . . H18A C18 H18B 107.736 no . . . C7 C19 H19A 109.471 no . . . C7 C19 H19B 109.467 no . . . C7 C19 H19C 109.471 no . . . H19A C19 H19B 109.471 no . . . H19A C19 H19C 109.474 no . . . H19B C19 H19C 109.473 no . . . O13 C20 H20A 109.469 no . . . O13 C20 H20B 109.471 no . . . O13 C20 H20C 109.472 no . . . H20A C20 H20B 109.476 no . . . H20A C20 H20C 109.473 no . . . H20B C20 H20C 109.466 no . . . C21 C22 H22 119.122 no . . . C23 C22 H22 119.121 no . . . C22 C23 H23 120.327 no . . . C24 C23 H23 120.322 no . . . C23 C24 H24 120.271 no . . . C25 C24 H24 120.265 no . . . C24 C25 H25 119.607 no . . . C26 C25 H25 119.611 no . . . C21 C26 H26 119.895 no . . . C25 C26 H26 119.905 no . . . 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C20 O13 C13 C12 -177.4(4) no . . . . C20 O13 C13 C14 3.9(7) no . . . . N2 N1 C5 O5 176.1(5) no . . . . N2 N1 C5 C4 -0.9(5) no . . . . C5 N1 N2 C3 -18.8(5) no . . . . N2 N1 C6 O6 162.9(4) no . . . . N2 N1 C6 C7 -21.4(6) no . . . . C6 N1 N2 C3 132.1(4) no . . . . C5 N1 C6 O6 -49.4(7) no . . . . C5 N1 C6 C7 126.3(5) no . . . . C6 N1 C5 O5 26.4(8) no . . . . C6 N1 C5 C4 -150.5(4) no . . . . N1 N2 C3 C4 30.3(4) no . . . . N1 N2 C3 C18 155.8(3) no . . . . N2 C3 C4 C5 -30.5(4) no . . . . N2 C3 C18 C21 169.3(4) no . . . . C4 C3 C18 C21 -72.8(6) no . . . . C18 C3 C4 C5 -151.3(4) no . . . . C3 C4 C5 O5 -157.2(5) no . . . . C3 C4 C5 N1 19.6(5) no . . . . O6 C6 C7 C8 120.0(5) no . . . . O6 C6 C7 C19 -3.6(7) no . . . . N1 C6 C7 C8 -55.5(5) no . . . . N1 C6 C7 C19 -179.1(4) no . . . . C6 C7 C8 C9 133.4(4) no . . . . C6 C7 C8 C17 -42.5(5) no . . . . C19 C7 C8 C9 -103.8(5) no . . . . C19 C7 C8 C17 80.4(5) no . . . . C7 C8 C9 C10 -173.4(4) no . . . . C7 C8 C17 C16 172.4(4) no . . . . C9 C8 C17 C16 -3.6(6) no . . . . C17 C8 C9 C10 2.5(6) no . . . . C8 C9 C10 C11 179.2(4) no . . . . C8 C9 C10 C15 0.8(6) no . . . . C9 C10 C11 C12 -176.5(4) no . . . . C9 C10 C15 C14 175.7(4) no . . . . C9 C10 C15 C16 -3.1(6) no . . . . C11 C10 C15 C14 -2.7(6) no . . . . C11 C10 C15 C16 178.5(4) no . . . . C15 C10 C11 C12 1.9(6) no . . . . C10 C11 C12 C13 1.1(7) no . . . . C11 C12 C13 O13 177.9(4) no . . . . C11 C12 C13 C14 -3.4(7) no . . . . O13 C13 C14 C15 -178.9(4) no . . . . C12 C13 C14 C15 2.5(7) no . . . . C13 C14 C15 C10 0.5(7) no . . . . C13 C14 C15 C16 179.2(4) no . . . . C10 C15 C16 C17 2.0(6) no . . . . C14 C15 C16 C17 -176.7(4) no . . . . C15 C16 C17 C8 1.4(7) no . . . . C3 C18 C21 C22 -74.3(6) no . . . . C3 C18 C21 C26 106.4(5) no . . . . C18 C21 C22 C23 -178.6(5) no . . . . C18 C21 C26 C25 178.5(5) no . . . . C22 C21 C26 C25 -0.8(8) no . . . . C26 C21 C22 C23 0.7(8) no . . . . C21 C22 C23 C24 -0.4(9) no . . . . C22 C23 C24 C25 0.1(9) no . . . . C23 C24 C25 C26 -0.2(10) no . . . . C24 C25 C26 C21 0.6(9) no . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 O5 O6 2.868(5) no . . O5 N2 3.508(6) no . . O5 C3 3.531(7) no . . O5 C6 2.900(5) no . . O6 N2 3.529(6) no . . O6 C5 2.914(6) no . . O6 C8 3.410(7) no . . O6 C17 3.513(7) no . . O6 C19 2.787(7) no . . N1 C8 2.899(6) no . . N1 C17 3.178(7) no . . N2 C7 2.809(6) no . . N2 C8 2.942(6) no . . N2 C9 3.289(7) no . . N2 C17 3.582(7) no . . C3 C6 3.476(7) no . . C3 C8 3.384(6) no . . C3 C9 3.506(6) no . . C3 C22 3.229(8) no . . C3 C26 3.499(8) no . . C4 C21 3.238(8) no . . C5 C17 3.402(7) no . . C6 C17 2.854(8) no . . C8 C15 2.829(7) no . . C9 C16 2.778(6) no . . C9 C19 3.484(8) no . . C10 C13 2.796(7) no . . C10 C17 2.796(8) no . . C11 C14 2.807(7) no . . C12 C15 2.797(8) no . . C14 C20 2.797(8) no . . C17 C19 3.284(7) no . . C21 C24 2.790(8) no . . C22 C25 2.744(7) no . . C23 C26 2.771(9) no . . O5 N1 3.371(6) no . 2_647 O5 N2 3.217(6) no . 2_647 O5 C11 3.165(7) no . 1_455 O5 C12 3.297(6) no . 1_455 O5 C17 3.554(7) no . 2_657 O6 N1 3.501(6) no . 2_647 O6 N2 3.299(6) no . 2_647 O6 C3 3.555(7) no . 2_647 O6 C4 3.214(7) no . 2_647 O6 C5 3.489(7) no . 2_647 O13 C23 3.437(9) no . 2_746 N1 O5 3.371(6) no . 2_657 N1 O6 3.501(6) no . 2_657 N2 O5 3.217(6) no . 2_657 N2 O6 3.299(6) no . 2_657 N2 C11 3.525(6) no . 2_757 C3 O6 3.555(7) no . 2_657 C4 O6 3.214(7) no . 2_657 C5 O6 3.489(7) no . 2_657 C11 O5 3.165(7) no . 1_655 C11 N2 3.525(6) no . 2_747 C12 O5 3.297(6) no . 1_655 C17 O5 3.554(7) no . 2_647 C23 O13 3.437(9) no . 2_756 O5 H4A 2.9028 no . . O5 H4B 2.6894 no . . O5 H17 3.2595 no . . O6 H7 3.0455 no . . O6 H17 2.9761 no . . O6 H19A 2.7079 no . . O6 H19B 2.7368 no . . O13 H12 2.4717 no . . O13 H14 2.6501 no . . O13 H23 3.3061 no . . N1 H3 2.6976 no . . N1 H4A 2.8627 no . . N1 H4B 3.1059 no . . N1 H7 2.7241 no . . N1 H17 3.1346 no . . N2 H4A 2.8034 no . . N2 H4B 3.1955 no . . N2 H7 2.6181 no . . N2 H9 3.4274 no . . N2 H18A 2.7133 no . . N2 H18B 2.5560 no . . C3 H22 3.1515 no . . C4 H2 2.65(5) no . . C4 H18A 2.7193 no . . C4 H18B 3.3969 no . . C4 H26 3.5971 no . . C5 H2 2.71(5) no . . C5 H3 2.7497 no . . C5 H17 3.2201 no . . C6 H2 2.97(5) no . . C6 H3 3.5890 no . . C6 H17 2.6328 no . . C6 H19A 2.7177 no . . C6 H19B 2.7126 no . . C6 H19C 3.3630 no . . C7 H2 3.51(4) no . . C7 H9 2.6782 no . . C7 H17 2.6800 no . . C8 H3 2.8415 no . . C8 H16 3.2801 no . . C8 H19A 2.7376 no . . C8 H19B 3.3727 no . . C8 H19C 2.7320 no . . C9 H3 2.8318 no . . C9 H7 2.5882 no . . C9 H11 2.6667 no . . C9 H17 3.2473 no . . C9 H19C 3.3453 no . . C10 H3 2.9201 no . . C10 H12 3.2696 no . . C10 H14 3.3119 no . . C10 H16 3.2869 no . . C10 H22 3.1412 no . . C11 H9 2.6592 no . . C11 H22 2.9431 no . . C12 H14 3.2718 no . . C12 H22 3.0291 no . . C13 H11 3.2762 no . . C13 H20A 2.5680 no . . C13 H20B 2.6390 no . . C13 H20C 3.1887 no . . C13 H22 3.2860 no . . C13 H23 3.3806 no . . C14 H12 3.2627 no . . C14 H16 2.6547 no . . C14 H20A 2.6840 no . . C14 H20B 2.7739 no . . C14 H22 3.5053 no . . C15 H3 2.9823 no . . C15 H9 3.3034 no . . C15 H11 3.3019 no . . C15 H17 3.2703 no . . C15 H22 3.4451 no . . C16 H3 3.0079 no . . C16 H14 2.6714 no . . C17 H3 2.9529 no . . C17 H7 3.3213 no . . C17 H9 3.2527 no . . C17 H19A 3.0457 no . . C18 H2 2.51(8) no . . C18 H4A 2.6684 no . . C18 H4B 3.0363 no . . C18 H22 2.6645 no . . C18 H26 2.6713 no . . C19 H9 3.5619 no . . C19 H17 3.2058 no . . C20 H14 2.5005 no . . C21 H3 2.6632 no . . C21 H4A 3.3217 no . . C21 H4B 3.2394 no . . C21 H23 3.2692 no . . C21 H25 3.2597 no . . C22 H3 2.9150 no . . C22 H18A 3.3009 no . . C22 H18B 2.6910 no . . C22 H24 3.2520 no . . C22 H26 3.2414 no . . C23 H25 3.2472 no . . C24 H22 3.2465 no . . C24 H26 3.2577 no . . C25 H23 3.2496 no . . C26 H4A 3.4853 no . . C26 H4B 3.5854 no . . C26 H18A 2.5646 no . . C26 H18B 3.1995 no . . C26 H22 3.2370 no . . C26 H24 3.2617 no . . H2 H3 2.8059 no . . H2 H4A 2.7315 no . . H2 H4B 3.5909 no . . H2 H7 3.1748 no . . H2 H18A 2.4099 no . . H2 H18B 2.6269 no . . H3 H4A 2.8582 no . . H3 H4B 2.2637 no . . H3 H9 3.3562 no . . H3 H17 3.5386 no . . H3 H18A 2.8630 no . . H3 H18B 2.4201 no . . H3 H22 2.6448 no . . H4A H18A 2.4422 no . . H4A H18B 3.5529 no . . H4A H26 3.1289 no . . H4B H18A 3.3055 no . . H7 H9 2.3950 no . . H7 H19A 2.8691 no . . H7 H19B 2.3648 no . . H7 H19C 2.3691 no . . H9 H11 2.4963 no . . H9 H19C 3.2862 no . . H11 H12 2.3197 no . . H11 H22 3.3232 no . . H12 H22 3.4641 no . . H14 H16 2.5017 no . . H14 H20A 2.2575 no . . H14 H20B 2.3149 no . . H14 H20C 3.4708 no . . H16 H17 2.3054 no . . H17 H19A 2.7521 no . . H18A H22 3.5830 no . . H18A H26 2.3651 no . . H18B H22 2.5821 no . . H18B H26 3.4364 no . . H20A H23 3.4175 no . . H22 H23 2.3224 no . . H23 H24 2.3488 no . . H24 H25 2.3242 no . . H25 H26 2.3321 no . . O5 H2 2.45(7) no . 2_647 O5 H11 2.5432 no . 1_455 O5 H12 2.8056 no . 1_455 O5 H17 2.8304 no . 2_657 O5 H19A 3.2102 no . 2_657 O6 H2 2.49(6) no . 2_647 O6 H4A 2.5029 no . 2_647 O6 H16 3.0835 no . 2_657 O6 H17 3.2367 no . 2_657 O6 H18A 2.8709 no . 2_647 O6 H24 2.8083 no . 1_556 O13 H7 3.5581 no . 2_747 O13 H19B 3.0422 no . 2_747 O13 H19C 3.5317 no . 2_747 O13 H23 2.8955 no . 2_746 N1 H17 2.9275 no . 2_657 N2 H11 3.3366 no . 2_757 C3 H25 3.5130 no . 2_646 C4 H19A 3.1862 no . 2_657 C4 H20A 3.2783 no . 2_656 C4 H20C 3.5620 no . 2_656 C4 H25 3.2204 no . 2_646 C5 H2 3.42(7) no . 2_647 C5 H11 3.5553 no . 1_455 C5 H17 2.8477 no . 2_657 C5 H19A 3.2012 no . 2_657 C6 H2 3.38(6) no . 2_647 C6 H4A 3.4463 no . 2_647 C6 H17 3.4732 no . 2_657 C6 H24 3.3460 no . 1_556 C9 H18B 3.3167 no . 2_747 C10 H7 3.2099 no . 2_747 C10 H9 3.1989 no . 2_747 C11 H2 3.33(6) no . 2_747 C11 H7 2.9235 no . 2_747 C12 H7 2.7153 no . 2_747 C12 H20C 3.1180 no . 2_756 C13 H7 2.8390 no . 2_747 C13 H19B 3.3077 no . 2_747 C13 H19C 3.4565 no . 2_747 C14 H7 3.0893 no . 2_747 C14 H9 3.4486 no . 2_747 C14 H18B 3.4759 no . 1_545 C14 H19C 3.4521 no . 2_747 C14 H25 3.1540 no . 2_646 C15 H7 3.2649 no . 2_747 C15 H9 2.9048 no . 2_747 C15 H25 3.1554 no . 2_646 C16 H9 3.0592 no . 2_747 C16 H11 3.5396 no . 2_747 C16 H18A 3.0626 no . 1_545 C16 H18B 3.3941 no . 1_545 C16 H25 2.9155 no . 2_646 C17 H9 3.5003 no . 2_747 C17 H11 3.1634 no . 2_747 C18 H14 3.2710 no . 1_565 C18 H16 2.9742 no . 1_565 C19 H4A 3.2023 no . 2_647 C19 H20B 3.4221 no . 2_757 C19 H20C 3.4224 no . 1_556 C20 H4A 3.5042 no . 2_646 C20 H4B 3.2999 no . 2_646 C20 H12 3.2755 no . 2_746 C20 H19B 3.5102 no . 2_747 C20 H23 3.3145 no . 2_746 C21 H14 3.2876 no . 1_565 C21 H20B 3.3558 no . 1_565 C22 H19C 3.2345 no . 2_757 C22 H20B 3.2952 no . 1_565 C22 H26 3.4389 no . 2_646 C23 H19B 3.3899 no . 1_554 C23 H20B 3.3467 no . 1_565 C23 H26 2.9858 no . 2_646 C24 H4B 3.3704 no . 2_656 C24 H16 3.3384 no . 2_656 C24 H19B 3.5452 no . 1_554 C24 H20B 3.4471 no . 1_565 C24 H26 2.9509 no . 2_646 C25 H4B 2.8489 no . 2_656 C25 H14 3.2875 no . 2_656 C25 H16 3.2256 no . 2_656 C25 H20B 3.4923 no . 1_565 C25 H26 3.3786 no . 2_646 C26 H14 3.4105 no . 1_565 C26 H20A 3.4329 no . 2_656 C26 H20B 3.4550 no . 1_565 H2 O5 2.45(7) no . 2_657 H2 O6 2.49(6) no . 2_657 H2 C5 3.42(7) no . 2_657 H2 C6 3.38(6) no . 2_657 H2 C11 3.33(6) no . 2_757 H2 H11 2.8950 no . 2_757 H2 H16 3.2513 no . 1_565 H2 H17 3.5454 no . 2_657 H3 H25 2.9264 no . 2_646 H4A O6 2.5029 no . 2_657 H4A C6 3.4463 no . 2_657 H4A C19 3.2023 no . 2_657 H4A C20 3.5042 no . 2_656 H4A H19A 2.5012 no . 2_657 H4A H19B 3.1206 no . 2_657 H4A H20A 2.8894 no . 2_656 H4A H20C 3.2136 no . 2_656 H4B C20 3.2999 no . 2_656 H4B C24 3.3704 no . 2_646 H4B C25 2.8489 no . 2_646 H4B H12 3.5561 no . 1_455 H4B H19A 3.5830 no . 2_657 H4B H20A 2.7564 no . 2_656 H4B H20B 3.5436 no . 2_656 H4B H20C 3.1131 no . 2_656 H4B H24 3.3393 no . 2_646 H4B H25 2.3728 no . 2_646 H7 O13 3.5581 no . 2_757 H7 C10 3.2099 no . 2_757 H7 C11 2.9235 no . 2_757 H7 C12 2.7153 no . 2_757 H7 C13 2.8390 no . 2_757 H7 C14 3.0893 no . 2_757 H7 C15 3.2649 no . 2_757 H7 H11 3.4241 no . 2_757 H7 H12 3.1075 no . 2_757 H9 C10 3.1989 no . 2_757 H9 C14 3.4486 no . 2_757 H9 C15 2.9048 no . 2_757 H9 C16 3.0592 no . 2_757 H9 C17 3.5003 no . 2_757 H9 H16 3.3970 no . 2_757 H9 H18B 2.9333 no . 2_747 H11 O5 2.5432 no . 1_655 H11 N2 3.3366 no . 2_747 H11 C5 3.5553 no . 1_655 H11 C16 3.5396 no . 2_757 H11 C17 3.1634 no . 2_757 H11 H2 2.8950 no . 2_747 H11 H7 3.4241 no . 2_747 H11 H17 3.1133 no . 2_757 H11 H19A 3.0142 no . 2_757 H11 H19C 3.5305 no . 2_757 H12 O5 2.8056 no . 1_655 H12 C20 3.2755 no . 2_756 H12 H4B 3.5561 no . 1_655 H12 H7 3.1075 no . 2_747 H12 H19A 3.4669 no . 2_757 H12 H20B 3.3182 no . 2_756 H12 H20C 2.4377 no . 2_756 H12 H24 3.2705 no . 2_746 H14 C18 3.2710 no . 1_545 H14 C21 3.2876 no . 1_545 H14 C25 3.2875 no . 2_646 H14 C26 3.4105 no . 1_545 H14 H18A 2.9976 no . 1_545 H14 H18B 3.0121 no . 1_545 H14 H19C 3.3983 no . 2_747 H14 H25 2.9100 no . 2_646 H14 H26 3.4210 no . 1_545 H16 O6 3.0835 no . 2_647 H16 C18 2.9742 no . 1_545 H16 C24 3.3384 no . 2_646 H16 C25 3.2256 no . 2_646 H16 H2 3.2513 no . 1_545 H16 H9 3.3970 no . 2_747 H16 H18A 2.2108 no . 1_545 H16 H18B 2.8783 no . 1_545 H16 H24 2.9029 no . 2_646 H16 H25 2.6722 no . 2_646 H17 O5 2.8304 no . 2_647 H17 O6 3.2367 no . 2_647 H17 N1 2.9275 no . 2_647 H17 C5 2.8477 no . 2_647 H17 C6 3.4732 no . 2_647 H17 H2 3.5454 no . 2_647 H17 H11 3.1133 no . 2_747 H18A O6 2.8709 no . 2_657 H18A C16 3.0626 no . 1_565 H18A H14 2.9976 no . 1_565 H18A H16 2.2108 no . 1_565 H18A H24 3.2805 no . 2_656 H18B C9 3.3167 no . 2_757 H18B C14 3.4759 no . 1_565 H18B C16 3.3941 no . 1_565 H18B H9 2.9333 no . 2_757 H18B H14 3.0121 no . 1_565 H18B H16 2.8783 no . 1_565 H18B H19C 3.0259 no . 2_757 H19A O5 3.2102 no . 2_647 H19A C4 3.1862 no . 2_647 H19A C5 3.2012 no . 2_647 H19A H4A 2.5012 no . 2_647 H19A H4B 3.5830 no . 2_647 H19A H11 3.0142 no . 2_747 H19A H12 3.4669 no . 2_747 H19A H20A 3.5914 no . 1_556 H19A H20C 2.9094 no . 1_556 H19B O13 3.0422 no . 2_757 H19B C13 3.3077 no . 2_757 H19B C20 3.5102 no . 2_757 H19B C23 3.3899 no . 1_556 H19B C24 3.5452 no . 1_556 H19B H4A 3.1206 no . 2_647 H19B H20B 3.0756 no . 2_757 H19B H20C 3.3585 no . 1_556 H19B H23 2.6747 no . 1_556 H19B H24 2.9951 no . 1_556 H19C O13 3.5317 no . 2_757 H19C C13 3.4565 no . 2_757 H19C C14 3.4521 no . 2_757 H19C C22 3.2345 no . 2_747 H19C H11 3.5305 no . 2_747 H19C H14 3.3983 no . 2_757 H19C H18B 3.0259 no . 2_747 H19C H20B 2.8666 no . 2_757 H19C H20C 3.4591 no . 1_556 H19C H22 2.8610 no . 2_747 H20A C4 3.2783 no . 2_646 H20A C26 3.4329 no . 2_646 H20A H4A 2.8894 no . 2_646 H20A H4B 2.7564 no . 2_646 H20A H19A 3.5914 no . 1_554 H20A H26 3.1075 no . 2_646 H20B C19 3.4221 no . 2_747 H20B C21 3.3558 no . 1_545 H20B C22 3.2952 no . 1_545 H20B C23 3.3467 no . 1_545 H20B C24 3.4471 no . 1_545 H20B C25 3.4923 no . 1_545 H20B C26 3.4550 no . 1_545 H20B H4B 3.5436 no . 2_646 H20B H12 3.3182 no . 2_746 H20B H19B 3.0756 no . 2_747 H20B H19C 2.8666 no . 2_747 H20B H23 3.4790 no . 2_746 H20C C4 3.5620 no . 2_646 H20C C12 3.1180 no . 2_746 H20C C19 3.4224 no . 1_554 H20C H4A 3.2136 no . 2_646 H20C H4B 3.1131 no . 2_646 H20C H12 2.4377 no . 2_746 H20C H19A 2.9094 no . 1_554 H20C H19B 3.3585 no . 1_554 H20C H19C 3.4591 no . 1_554 H20C H23 2.9841 no . 2_746 H22 H19C 2.8610 no . 2_757 H23 O13 2.8955 no . 2_756 H23 C20 3.3145 no . 2_756 H23 H19B 2.6747 no . 1_554 H23 H20B 3.4790 no . 2_756 H23 H20C 2.9841 no . 2_756 H23 H26 3.2528 no . 2_646 H24 O6 2.8083 no . 1_554 H24 C6 3.3460 no . 1_554 H24 H4B 3.3393 no . 2_656 H24 H12 3.2705 no . 2_756 H24 H16 2.9029 no . 2_656 H24 H18A 3.2805 no . 2_646 H24 H19B 2.9951 no . 1_554 H24 H26 3.1973 no . 2_646 H25 C3 3.5130 no . 2_656 H25 C4 3.2204 no . 2_656 H25 C14 3.1540 no . 2_656 H25 C15 3.1554 no . 2_656 H25 C16 2.9155 no . 2_656 H25 H3 2.9264 no . 2_656 H25 H4B 2.3728 no . 2_656 H25 H14 2.9100 no . 2_656 H25 H16 2.6722 no . 2_656 H26 C22 3.4389 no . 2_656 H26 C23 2.9858 no . 2_656 H26 C24 2.9509 no . 2_656 H26 C25 3.3786 no . 2_656 H26 H14 3.4210 no . 1_565 H26 H20A 3.1075 no . 2_656 H26 H23 3.2528 no . 2_656 H26 H24 3.1973 no . 2_656 #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #============================================================================== _database_code_depnum_ccdc_archive 'CCDC 956168' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_19 # CHEMICAL DATA _chemical_formula_sum 'C18 H17 F3 N2 O3' _chemical_formula_moiety 'C18 H17 F3 N2 O3' _chemical_formula_weight 366.34 _chemical_melting_point ? _chemical_absolute_configuration syn #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2 1' _symmetry_space_group_name_Hall 'C 2y' _symmetry_Int_Tables_number 5 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,+Y,-Z 3 1/2+X,1/2+Y,+Z 4 1/2-X,1/2+Y,-Z #------------------------------------------------------------------------------ _cell_length_a 24.538(15) _cell_length_b 5.643(5) _cell_length_c 11.947(9) _cell_angle_alpha 90.0000 _cell_angle_beta 95.19(2) _cell_angle_gamma 90.0000 _cell_volume 1647(2) _cell_formula_units_Z 4 _cell_measurement_reflns_used 2508 _cell_measurement_theta_min 2.50 _cell_measurement_theta_max 25.35 _cell_measurement_temperature 93 #------------------------------------------------------------------------------ _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.010 _exptl_crystal_size_min 0.010 _exptl_crystal_density_diffrn 1.477 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760.00 _exptl_absorpt_coefficient_mu 0.123 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'REQAB (Rigaku, 1998)' _exptl_absorpt_correction_T_min 0.564 _exptl_absorpt_correction_T_max 0.999 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 93 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_measurement_device_type 'Rigaku Mercury70' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 14.629 _diffrn_reflns_number 5260 _diffrn_reflns_av_R_equivalents 0.0620 _diffrn_reflns_theta_min 2.495 _diffrn_reflns_theta_max 25.301 _diffrn_reflns_theta_full 25.000 _diffrn_measured_fraction_theta_max 0.979 _diffrn_measured_fraction_theta_full 0.979 _diffrn_reflns_Laue_measured_fraction_max 0.979 _diffrn_reflns_Laue_measured_fraction_full 0.979 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 10 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 2769 _reflns_number_gt 1873 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0695 _refine_ls_wR_factor_ref 0.2148 _refine_ls_number_restraints 2 _refine_ls_hydrogen_treatment mixed _refine_ls_number_reflns 2769 _refine_ls_number_parameters 239 _refine_ls_goodness_of_fit_ref 0.886 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.1349P)^2^+0.9129P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.042 _refine_diff_density_max 0.280 _refine_diff_density_min -0.370 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Parsons and Flack (2004), Acta Cryst. A60, s61.' _refine_ls_abs_structure_Flack 2.5(10) 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 for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; F F 0.0171 0.0103 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; N N 0.0061 0.0033 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.0106 0.0060 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 0.70839(18) 0.3464(10) 0.6327(4) 0.0495(13) Uani 1.0 4 d . . . F2 F 0.76382(17) 0.0839(10) 0.5749(4) 0.0538(14) Uani 1.0 4 d . . . F3 F 0.67869(17) -0.0016(11) 0.5805(4) 0.0539(15) Uani 1.0 4 d . . . O5 O 0.76871(19) 0.5399(11) 0.9141(4) 0.0425(14) Uani 1.0 4 d . . . O6 O 0.65738(19) 0.6326(10) 0.9314(4) 0.0388(13) Uani 1.0 4 d . . . O13 O 0.3798(2) 1.3727(11) 0.6601(5) 0.0448(14) Uani 1.0 4 d . . . N1 N 0.6942(3) 0.2954(12) 0.8673(5) 0.0354(16) Uani 1.0 4 d . . . N2 N 0.6840(3) 0.0693(13) 0.8150(6) 0.0395(16) Uani 1.0 4 d . . . C3 C 0.7329(3) 0.0233(16) 0.7538(6) 0.0367(18) Uani 1.0 4 d . . . C4 C 0.7788(3) 0.1589(16) 0.8206(6) 0.0387(18) Uani 1.0 4 d . . . C5 C 0.7503(3) 0.3557(18) 0.8749(6) 0.0385(18) Uani 1.0 4 d . . . C6 C 0.6498(3) 0.4481(15) 0.8825(6) 0.0340(17) Uani 1.0 4 d . . . C7 C 0.5939(3) 0.3563(15) 0.8360(6) 0.0332(17) Uani 1.0 4 d . . . C8 C 0.5584(3) 0.5612(15) 0.7935(6) 0.0353(18) Uani 1.0 4 d . . . C9 C 0.5083(3) 0.6163(15) 0.8314(6) 0.0364(18) Uani 1.0 4 d . . . C10 C 0.4761(3) 0.8057(16) 0.7864(6) 0.0358(19) Uani 1.0 4 d . . . C11 C 0.4254(3) 0.8689(16) 0.8276(7) 0.0394(19) Uani 1.0 4 d . . . C12 C 0.3952(3) 1.0510(15) 0.7833(6) 0.0389(19) Uani 1.0 4 d . . . C13 C 0.4134(3) 1.1887(16) 0.6942(6) 0.0403(19) Uani 1.0 4 d . . . C14 C 0.4626(3) 1.1321(16) 0.6517(6) 0.0381(18) Uani 1.0 4 d . . . C15 C 0.4934(3) 0.9433(15) 0.6970(6) 0.0347(18) Uani 1.0 4 d . . . C16 C 0.5451(3) 0.8787(15) 0.6553(6) 0.0353(18) Uani 1.0 4 d . . . C17 C 0.5754(3) 0.6985(15) 0.7029(6) 0.0376(19) Uani 1.0 4 d . . . C18 C 0.7204(3) 0.1123(18) 0.6372(6) 0.042(2) Uani 1.0 4 d . . . C19 C 0.5712(4) 0.2090(16) 0.9295(7) 0.042(2) Uani 1.0 4 d . . . C20 C 0.3949(3) 1.5070(16) 0.5655(7) 0.0419(19) Uani 1.0 4 d . . . H2 H 0.686(4) -0.046(13) 0.877(6) 0.06(3) Uiso 1.0 4 d . . . H3 H 0.7413 -0.1500 0.7533 0.0441 Uiso 1.0 4 calc R . . H4A H 0.7985 0.0555 0.8778 0.0464 Uiso 1.0 4 calc R . . H4B H 0.8053 0.2218 0.7703 0.0464 Uiso 1.0 4 calc R . . H7 H 0.5991 0.2489 0.7713 0.0398 Uiso 1.0 4 calc R . . H9 H 0.4953 0.5234 0.8897 0.0437 Uiso 1.0 4 calc R . . H11 H 0.4126 0.7807 0.8877 0.0473 Uiso 1.0 4 calc R . . H12 H 0.3614 1.0880 0.8119 0.0467 Uiso 1.0 4 calc R . . H14 H 0.4752 1.2223 0.5920 0.0457 Uiso 1.0 4 calc R . . H16 H 0.5578 0.9637 0.5942 0.0423 Uiso 1.0 4 calc R . . H17 H 0.6094 0.6622 0.6747 0.0451 Uiso 1.0 4 calc R . . H19A H 0.5352 0.1456 0.9026 0.0505 Uiso 1.0 4 calc R . . H19B H 0.5677 0.3096 0.9953 0.0505 Uiso 1.0 4 calc R . . H19C H 0.5963 0.0777 0.9503 0.0505 Uiso 1.0 4 calc R . . H20A H 0.3952 1.4028 0.5000 0.0502 Uiso 1.0 4 calc R . . H20B H 0.4314 1.5748 0.5832 0.0502 Uiso 1.0 4 calc R . . H20C H 0.3684 1.6349 0.5490 0.0502 Uiso 1.0 4 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 F1 0.061(3) 0.043(4) 0.046(3) 0.011(3) 0.007(2) 0.013(3) F2 0.047(3) 0.070(4) 0.046(3) 0.002(3) 0.0115(18) -0.006(3) F3 0.049(3) 0.069(4) 0.043(3) -0.005(3) -0.0031(19) -0.010(3) O5 0.045(3) 0.042(4) 0.040(3) 0.003(3) -0.000(3) -0.003(3) O6 0.043(3) 0.029(4) 0.043(3) -0.001(3) 0.001(2) -0.001(3) O13 0.043(3) 0.040(4) 0.051(3) 0.004(3) 0.002(3) 0.008(3) N1 0.042(4) 0.024(4) 0.039(4) -0.002(3) -0.004(3) -0.004(3) N2 0.046(4) 0.033(5) 0.040(4) -0.004(3) 0.006(3) -0.000(3) C3 0.036(4) 0.029(5) 0.046(5) 0.002(4) 0.003(3) 0.001(4) C4 0.041(5) 0.035(5) 0.039(4) 0.007(4) -0.004(3) -0.002(4) C5 0.039(4) 0.040(6) 0.036(4) -0.007(4) 0.001(3) -0.005(4) C6 0.045(5) 0.024(5) 0.034(4) -0.003(4) 0.003(3) 0.004(4) C7 0.041(4) 0.023(5) 0.036(4) -0.005(4) 0.006(3) -0.001(4) C8 0.033(4) 0.039(6) 0.033(4) -0.003(4) -0.002(3) -0.003(4) C9 0.041(4) 0.034(5) 0.033(4) -0.007(4) 0.002(3) 0.004(4) C10 0.038(4) 0.039(6) 0.031(4) -0.012(4) 0.003(3) -0.007(4) C11 0.036(4) 0.041(6) 0.042(4) -0.001(4) 0.008(3) 0.002(4) C12 0.035(4) 0.036(6) 0.045(5) -0.002(4) 0.004(3) -0.002(4) C13 0.041(5) 0.037(6) 0.044(5) -0.003(4) 0.005(3) -0.004(4) C14 0.037(4) 0.039(5) 0.038(4) -0.006(4) 0.004(3) 0.000(4) C15 0.035(4) 0.037(5) 0.031(4) -0.006(4) -0.001(3) -0.005(4) C16 0.035(4) 0.035(5) 0.036(4) -0.006(4) 0.007(3) -0.006(4) C17 0.036(4) 0.041(6) 0.036(4) -0.005(4) 0.004(3) 0.003(4) C18 0.033(4) 0.046(6) 0.048(5) 0.001(4) 0.006(3) -0.003(5) C19 0.048(5) 0.032(5) 0.046(5) -0.007(4) 0.010(4) 0.002(4) C20 0.042(5) 0.036(6) 0.047(5) -0.003(4) -0.001(3) 0.002(4) #============================================================================== _computing_data_collection 'CrystalClear-SM Expert 2.0 rc13 (Rigaku, 2009)' _computing_cell_refinement 'CrystalClear-SM Expert 2.0 rc13' _computing_data_reduction 'CrystalClear-SM Expert 2.0 rc13' _computing_structure_solution 'SIR2004 (Burla, et al., 2005)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 F1 C18 1.354(12) yes . . F2 C18 1.362(9) yes . . F3 C18 1.340(9) yes . . O5 C5 1.210(11) yes . . O6 C6 1.200(10) yes . . O13 C13 1.365(10) yes . . O13 C20 1.437(10) yes . . N1 N2 1.433(10) yes . . N1 C5 1.413(10) yes . . N1 C6 1.413(10) yes . . N2 C3 1.485(10) yes . . C3 C4 1.526(10) yes . . C3 C18 1.486(11) yes . . C4 C5 1.493(12) yes . . C6 C7 1.525(10) yes . . C7 C8 1.508(11) yes . . C7 C19 1.536(11) yes . . C8 C9 1.382(10) yes . . C8 C17 1.424(11) yes . . C9 C10 1.407(11) yes . . C10 C11 1.424(11) yes . . C10 C15 1.416(11) yes . . C11 C12 1.347(12) yes . . C12 C13 1.421(12) yes . . C13 C14 1.391(11) yes . . C14 C15 1.387(11) yes . . C15 C16 1.452(11) yes . . C16 C17 1.354(11) yes . . N2 H2 0.98(7) no . . C3 H3 1.000 no . . C4 H4A 0.990 no . . C4 H4B 0.990 no . . C7 H7 1.000 no . . C9 H9 0.950 no . . C11 H11 0.950 no . . C12 H12 0.950 no . . C14 H14 0.950 no . . C16 H16 0.950 no . . C17 H17 0.950 no . . C19 H19A 0.980 no . . C19 H19B 0.980 no . . C19 H19C 0.980 no . . C20 H20A 0.980 no . . C20 H20B 0.980 no . . C20 H20C 0.980 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C13 O13 C20 116.4(6) yes . . . N2 N1 C5 111.9(7) yes . . . N2 N1 C6 119.5(6) yes . . . C5 N1 C6 127.0(7) yes . . . N1 N2 C3 104.7(6) yes . . . N2 C3 C4 104.2(6) yes . . . N2 C3 C18 107.2(6) yes . . . C4 C3 C18 113.6(7) yes . . . C3 C4 C5 104.3(6) yes . . . O5 C5 N1 124.0(8) yes . . . O5 C5 C4 129.3(7) yes . . . N1 C5 C4 106.6(7) yes . . . O6 C6 N1 120.3(7) yes . . . O6 C6 C7 124.5(7) yes . . . N1 C6 C7 115.1(7) yes . . . C6 C7 C8 109.6(7) yes . . . C6 C7 C19 107.0(6) yes . . . C8 C7 C19 115.1(6) yes . . . C7 C8 C9 124.4(7) yes . . . C7 C8 C17 118.2(7) yes . . . C9 C8 C17 117.2(7) yes . . . C8 C9 C10 122.1(7) yes . . . C9 C10 C11 122.5(7) yes . . . C9 C10 C15 120.6(7) yes . . . C11 C10 C15 117.0(7) yes . . . C10 C11 C12 121.4(8) yes . . . C11 C12 C13 120.9(7) yes . . . O13 C13 C12 114.7(7) yes . . . O13 C13 C14 126.0(8) yes . . . C12 C13 C14 119.3(8) yes . . . C13 C14 C15 119.6(7) yes . . . C10 C15 C14 121.8(7) yes . . . C10 C15 C16 116.8(7) yes . . . C14 C15 C16 121.4(7) yes . . . C15 C16 C17 120.6(7) yes . . . C8 C17 C16 122.6(7) yes . . . F1 C18 F2 105.8(7) yes . . . F1 C18 F3 107.1(6) yes . . . F1 C18 C3 113.1(7) yes . . . F2 C18 F3 105.5(6) yes . . . F2 C18 C3 111.5(6) yes . . . F3 C18 C3 113.3(7) yes . . . N1 N2 H2 105(4) no . . . C3 N2 H2 106(5) no . . . N2 C3 H3 110.507 no . . . C4 C3 H3 110.506 no . . . C18 C3 H3 110.502 no . . . C3 C4 H4A 110.893 no . . . C3 C4 H4B 110.887 no . . . C5 C4 H4A 110.898 no . . . C5 C4 H4B 110.895 no . . . H4A C4 H4B 108.920 no . . . C6 C7 H7 108.305 no . . . C8 C7 H7 108.319 no . . . C19 C7 H7 108.311 no . . . C8 C9 H9 118.956 no . . . C10 C9 H9 118.959 no . . . C10 C11 H11 119.279 no . . . C12 C11 H11 119.284 no . . . C11 C12 H12 119.550 no . . . C13 C12 H12 119.550 no . . . C13 C14 H14 120.192 no . . . C15 C14 H14 120.201 no . . . C15 C16 H16 119.712 no . . . C17 C16 H16 119.706 no . . . C8 C17 H17 118.679 no . . . C16 C17 H17 118.678 no . . . C7 C19 H19A 109.470 no . . . C7 C19 H19B 109.471 no . . . C7 C19 H19C 109.471 no . . . H19A C19 H19B 109.470 no . . . H19A C19 H19C 109.475 no . . . H19B C19 H19C 109.470 no . . . O13 C20 H20A 109.474 no . . . O13 C20 H20B 109.459 no . . . O13 C20 H20C 109.481 no . . . H20A C20 H20B 109.466 no . . . H20A C20 H20C 109.478 no . . . H20B C20 H20C 109.469 no . . . 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C20 O13 C13 C12 -176.2(6) no . . . . C20 O13 C13 C14 5.4(10) no . . . . N2 N1 C5 O5 178.7(7) no . . . . N2 N1 C5 C4 1.8(8) no . . . . C5 N1 N2 C3 -19.2(7) no . . . . N2 N1 C6 O6 176.1(6) no . . . . N2 N1 C6 C7 -2.2(9) no . . . . C6 N1 N2 C3 147.8(6) no . . . . C5 N1 C6 O6 -19.2(11) no . . . . C5 N1 C6 C7 162.6(6) no . . . . C6 N1 C5 O5 12.9(12) no . . . . C6 N1 C5 C4 -163.9(6) no . . . . N1 N2 C3 C4 27.9(7) no . . . . N1 N2 C3 C18 -92.9(6) no . . . . N2 C3 C4 C5 -26.9(7) no . . . . N2 C3 C18 F1 59.1(8) no . . . . N2 C3 C18 F2 178.2(6) no . . . . N2 C3 C18 F3 -62.9(9) no . . . . C4 C3 C18 F1 -55.5(8) no . . . . C4 C3 C18 F2 63.6(9) no . . . . C4 C3 C18 F3 -177.6(6) no . . . . C18 C3 C4 C5 89.5(7) no . . . . C3 C4 C5 O5 -160.9(8) no . . . . C3 C4 C5 N1 15.8(8) no . . . . O6 C6 C7 C8 35.4(10) no . . . . O6 C6 C7 C19 -90.0(9) no . . . . N1 C6 C7 C8 -146.4(6) no . . . . N1 C6 C7 C19 88.2(7) no . . . . C6 C7 C8 C9 -122.0(7) no . . . . C6 C7 C8 C17 62.4(8) no . . . . C19 C7 C8 C9 -1.4(10) no . . . . C19 C7 C8 C17 -176.9(6) no . . . . C7 C8 C9 C10 -178.1(6) no . . . . C7 C8 C17 C16 176.8(6) no . . . . C9 C8 C17 C16 0.9(11) no . . . . C17 C8 C9 C10 -2.5(11) no . . . . C8 C9 C10 C11 -177.8(7) no . . . . C8 C9 C10 C15 2.0(11) no . . . . C9 C10 C11 C12 180.0(7) no . . . . C9 C10 C15 C14 -179.5(6) no . . . . C9 C10 C15 C16 0.1(10) no . . . . C11 C10 C15 C14 0.4(11) no . . . . C11 C10 C15 C16 179.9(6) no . . . . C15 C10 C11 C12 0.1(11) no . . . . C10 C11 C12 C13 -0.7(12) no . . . . C11 C12 C13 O13 -177.8(7) no . . . . C11 C12 C13 C14 0.7(11) no . . . . O13 C13 C14 C15 178.1(7) no . . . . C12 C13 C14 C15 -0.2(11) no . . . . C13 C14 C15 C10 -0.3(11) no . . . . C13 C14 C15 C16 -179.8(6) no . . . . C10 C15 C16 C17 -1.6(10) no . . . . C14 C15 C16 C17 177.9(7) no . . . . C15 C16 C17 C8 1.1(11) no . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 F1 N1 2.870(8) no . . F1 N2 2.790(9) no . . F1 C4 2.906(9) no . . F1 C5 2.982(9) no . . F1 C6 3.475(9) no . . F2 C4 2.956(9) no . . F3 N2 2.822(8) no . . O5 O6 2.807(7) no . . O5 N2 3.511(9) no . . O5 C3 3.554(10) no . . O5 C6 2.953(9) no . . O6 N2 3.553(9) no . . O6 C5 2.893(10) no . . O6 C8 2.838(8) no . . O6 C17 3.262(9) no . . O6 C19 3.190(10) no . . O13 C11 3.597(11) no . . N1 C18 3.060(10) no . . N1 C19 3.209(11) no . . N2 C7 2.771(10) no . . N2 C19 3.291(11) no . . C3 C6 3.583(11) no . . C5 C18 3.180(11) no . . C6 C9 3.598(11) no . . C6 C17 3.037(11) no . . C8 C15 2.862(11) no . . C9 C16 2.788(11) no . . C9 C19 2.952(12) no . . C10 C13 2.820(12) no . . C10 C17 2.782(11) no . . C11 C14 2.794(12) no . . C12 C15 2.771(11) no . . C14 C20 2.826(12) no . . F1 F2 2.953(7) no . 4_656 F1 C20 3.431(9) no . 2_646 F2 F1 2.953(7) no . 4_646 F2 F2 3.376(8) no . 4_646 F2 F2 3.376(8) no . 4_656 F2 F3 3.373(8) no . 4_656 F2 O13 3.167(7) no . 3_535 F2 C20 3.257(9) no . 3_535 F3 F2 3.373(8) no . 4_646 F3 C16 3.540(9) no . 1_545 F3 C17 3.478(10) no . 1_545 O5 O6 3.372(8) no . 4_647 O5 N1 3.049(8) no . 4_657 O5 N2 3.341(8) no . 4_657 O5 C3 3.403(10) no . 1_565 O5 C4 3.539(10) no . 4_657 O5 C5 3.156(10) no . 4_657 O6 O5 3.372(8) no . 4_657 O6 N2 2.932(9) no . 1_565 O6 C4 3.226(9) no . 4_657 O6 C5 3.335(9) no . 4_657 O13 F2 3.167(7) no . 3_465 O13 C11 3.563(11) no . 1_565 N1 O5 3.049(8) no . 4_647 N2 O5 3.341(8) no . 4_647 N2 O6 2.932(9) no . 1_545 N2 C17 3.553(10) no . 1_545 C3 O5 3.403(10) no . 1_545 C4 O5 3.539(10) no . 4_647 C4 O6 3.226(9) no . 4_647 C5 O5 3.156(10) no . 4_647 C5 O6 3.335(9) no . 4_647 C7 C16 3.590(11) no . 1_545 C9 C14 3.591(12) no . 1_545 C10 C19 3.582(12) no . 1_565 C10 C20 3.581(11) no . 1_545 C11 O13 3.563(11) no . 1_545 C11 C19 3.473(12) no . 2_667 C12 C19 3.568(11) no . 2_667 C14 C9 3.591(12) no . 1_565 C15 C19 3.557(11) no . 1_565 C16 F3 3.540(9) no . 1_565 C16 C7 3.590(11) no . 1_565 C17 F3 3.478(10) no . 1_565 C17 N2 3.553(10) no . 1_565 C17 C20 3.522(11) no . 2_646 C19 C10 3.582(12) no . 1_545 C19 C11 3.473(12) no . 2_647 C19 C12 3.568(11) no . 2_647 C19 C15 3.557(11) no . 1_545 C20 F1 3.431(9) no . 2_666 C20 F2 3.257(9) no . 3_465 C20 C10 3.581(11) no . 1_565 C20 C17 3.522(11) no . 2_666 F1 H3 3.2195 no . . F1 H4B 2.8545 no . . F1 H7 3.3228 no . . F1 H17 3.0890 no . . F2 H3 2.6081 no . . F2 H4B 2.5817 no . . F3 H2 3.54(7) no . . F3 H3 2.5985 no . . F3 H7 3.4374 no . . O5 H4A 2.8721 no . . O5 H4B 2.6944 no . . O6 H7 3.1464 no . . O6 H17 3.1879 no . . O6 H19B 3.0078 no . . O6 H19C 3.4877 no . . O13 H12 2.4948 no . . O13 H14 2.6852 no . . N1 H3 3.1305 no . . N1 H4A 2.8882 no . . N1 H4B 3.0866 no . . N1 H7 2.5198 no . . N1 H19B 3.5820 no . . N1 H19C 2.9487 no . . N2 H4A 2.8429 no . . N2 H4B 3.1907 no . . N2 H7 2.3334 no . . N2 H19C 2.8061 no . . C3 H7 3.5464 no . . C4 H2 2.69(9) no . . C5 H2 2.76(8) no . . C5 H3 3.2011 no . . C6 H2 2.93(7) no . . C6 H17 2.8563 no . . C6 H19A 3.3171 no . . C6 H19B 2.6415 no . . C6 H19C 2.6353 no . . C7 H2 3.21(8) no . . C7 H9 2.7262 no . . C7 H17 2.6403 no . . C8 H16 3.2898 no . . C8 H19A 2.7667 no . . C8 H19B 2.7898 no . . C8 H19C 3.3915 no . . C9 H7 3.1721 no . . C9 H11 2.6682 no . . C9 H17 3.2506 no . . C9 H19A 2.8484 no . . C9 H19B 2.9051 no . . C10 H12 3.2730 no . . C10 H14 3.3036 no . . C10 H16 3.3056 no . . C11 H9 2.6575 no . . C12 H14 3.2891 no . . C13 H11 3.2641 no . . C13 H20A 2.6183 no . . C13 H20B 2.6090 no . . C13 H20C 3.1969 no . . C14 H12 3.2808 no . . C14 H16 2.6689 no . . C14 H20A 2.7957 no . . C14 H20B 2.7169 no . . C15 H9 3.3008 no . . C15 H11 3.2829 no . . C15 H17 3.2921 no . . C16 H14 2.6534 no . . C17 H7 2.7119 no . . C17 H9 3.2583 no . . C18 H2 3.18(7) no . . C18 H4A 3.3224 no . . C18 H4B 2.5792 no . . C18 H7 3.5907 no . . C19 H2 3.27(9) no . . C19 H9 2.5859 no . . C20 H14 2.5398 no . . H2 H3 2.1756 no . . H2 H4A 2.8186 no . . H2 H7 2.9001 no . . H2 H19C 2.5393 no . . H3 H4A 2.2690 no . . H3 H4B 2.6177 no . . H7 H9 3.3968 no . . H7 H17 2.6243 no . . H7 H19A 2.3873 no . . H7 H19B 2.8716 no . . H7 H19C 2.3532 no . . H9 H11 2.4939 no . . H9 H19A 2.3457 no . . H9 H19B 2.4089 no . . H9 H19C 3.5590 no . . H11 H12 2.2801 no . . H14 H16 2.4967 no . . H14 H20A 2.3895 no . . H14 H20B 2.2583 no . . H14 H20C 3.5087 no . . H16 H17 2.2811 no . . F1 H3 3.2542 no . 1_565 F1 H20A 2.8889 no . 2_646 F1 H20C 3.1895 no . 2_646 F2 H20A 3.5719 no . 3_535 F2 H20C 2.6279 no . 3_535 F3 H16 2.9911 no . 1_545 F3 H17 2.8463 no . 1_545 F3 H20A 3.0169 no . 2_646 F3 H20C 2.7587 no . 2_636 O5 H2 3.10(8) no . 1_565 O5 H2 2.68(7) no . 4_657 O5 H3 2.6406 no . 1_565 O5 H4A 3.0411 no . 1_565 O5 H4A 3.1063 no . 4_657 O5 H12 2.6896 no . 3_545 O5 H19C 3.5601 no . 4_657 O6 H2 2.07(8) no . 1_565 O6 H3 3.3275 no . 1_565 O6 H4A 2.4718 no . 4_657 O6 H11 2.9975 no . 2_657 O6 H19C 2.9443 no . 1_565 O13 H4A 3.5696 no . 3_465 O13 H4B 3.0634 no . 3_465 O13 H11 3.5981 no . 1_565 N1 H4A 3.3702 no . 4_657 N2 H17 3.2984 no . 1_545 C4 H11 3.3775 no . 3_545 C4 H12 3.1641 no . 3_545 C5 H2 3.27(7) no . 4_657 C5 H3 3.1435 no . 1_565 C5 H4A 3.4745 no . 4_657 C5 H12 3.1753 no . 3_545 C6 H2 2.99(7) no . 1_565 C6 H4A 3.0849 no . 4_657 C8 H14 3.5678 no . 1_545 C8 H19C 3.5432 no . 1_565 C9 H9 3.3816 no . 2_657 C9 H19A 3.1587 no . 1_565 C9 H19B 3.3854 no . 2_657 C9 H19C 3.5914 no . 1_565 C9 H20B 3.3761 no . 1_545 C10 H19A 2.7104 no . 1_565 C10 H20B 2.8834 no . 1_545 C11 H4B 3.0774 no . 3_455 C11 H19A 3.1730 no . 1_565 C11 H19B 3.2590 no . 2_667 C11 H19C 2.9942 no . 2_667 C11 H20B 3.3739 no . 1_545 C12 H4B 2.8771 no . 3_455 C12 H19B 3.0844 no . 2_667 C12 H19C 3.1743 no . 2_667 C13 H9 3.4950 no . 1_565 C14 H7 3.5801 no . 1_565 C14 H14 3.4446 no . 2_656 C14 H16 3.0852 no . 2_656 C14 H19A 3.3461 no . 1_565 C14 H20B 3.3220 no . 1_545 C15 H7 3.1737 no . 1_565 C15 H16 3.5923 no . 2_656 C15 H19A 2.8166 no . 1_565 C15 H20B 2.8478 no . 1_545 C16 H7 2.7752 no . 1_565 C16 H14 3.5315 no . 2_656 C16 H19A 3.3438 no . 1_565 C16 H20B 3.3216 no . 1_545 C16 H20B 3.4192 no . 2_646 C17 H2 3.57(8) no . 1_565 C17 H7 3.2502 no . 1_565 C17 H20A 3.0813 no . 2_646 C17 H20B 3.4778 no . 2_646 C17 H20C 3.4403 no . 2_646 C18 H20A 3.5470 no . 2_646 C19 H9 3.3337 no . 2_657 C19 H11 3.2572 no . 2_647 C19 H12 3.4375 no . 2_647 C19 H19A 3.4528 no . 2_657 C20 H16 3.4682 no . 2_666 C20 H17 2.9939 no . 2_666 H2 O5 3.10(8) no . 1_545 H2 O5 2.68(7) no . 4_647 H2 O6 2.07(8) no . 1_545 H2 C5 3.27(7) no . 4_647 H2 C6 2.99(7) no . 1_545 H2 C17 3.57(8) no . 1_545 H2 H17 3.3544 no . 1_545 H3 F1 3.2542 no . 1_545 H3 O5 2.6406 no . 1_545 H3 O6 3.3275 no . 1_545 H3 C5 3.1435 no . 1_545 H3 H12 3.3132 no . 3_535 H3 H17 3.4539 no . 1_545 H4A O5 3.0411 no . 1_545 H4A O5 3.1063 no . 4_647 H4A O6 2.4718 no . 4_647 H4A O13 3.5696 no . 3_535 H4A N1 3.3702 no . 4_647 H4A C5 3.4745 no . 4_647 H4A C6 3.0849 no . 4_647 H4A H11 3.0664 no . 3_545 H4A H12 3.1904 no . 3_535 H4A H12 3.4991 no . 3_545 H4B O13 3.0634 no . 3_535 H4B C11 3.0774 no . 3_545 H4B C12 2.8771 no . 3_545 H4B H11 2.8867 no . 3_545 H4B H12 2.5065 no . 3_545 H4B H20C 3.2195 no . 3_535 H7 C14 3.5801 no . 1_545 H7 C15 3.1737 no . 1_545 H7 C16 2.7752 no . 1_545 H7 C17 3.2502 no . 1_545 H7 H14 3.5599 no . 1_545 H7 H16 2.7754 no . 1_545 H7 H17 3.5226 no . 1_545 H7 H20A 3.3700 no . 2_646 H9 C9 3.3816 no . 2_657 H9 C13 3.4950 no . 1_545 H9 C19 3.3337 no . 2_657 H9 H9 2.6244 no . 2_657 H9 H19A 3.4057 no . 2_657 H9 H19B 2.4733 no . 2_657 H11 O6 2.9975 no . 2_657 H11 O13 3.5981 no . 1_545 H11 C4 3.3775 no . 3_455 H11 C19 3.2572 no . 2_667 H11 H4A 3.0664 no . 3_455 H11 H4B 2.8867 no . 3_455 H11 H19A 3.4024 no . 2_667 H11 H19B 3.0215 no . 2_657 H11 H19B 3.3124 no . 2_667 H11 H19C 2.5842 no . 2_667 H12 O5 2.6896 no . 3_455 H12 C4 3.1641 no . 3_455 H12 C5 3.1753 no . 3_455 H12 C19 3.4375 no . 2_667 H12 H3 3.3132 no . 3_465 H12 H4A 3.4991 no . 3_455 H12 H4A 3.1904 no . 3_465 H12 H4B 2.5065 no . 3_455 H12 H19B 3.0276 no . 2_667 H12 H19C 2.9356 no . 2_667 H14 C8 3.5678 no . 1_565 H14 C14 3.4446 no . 2_656 H14 C16 3.5315 no . 2_656 H14 H7 3.5599 no . 1_565 H14 H14 2.6072 no . 2_656 H14 H16 2.7216 no . 2_656 H16 F3 2.9911 no . 1_565 H16 C14 3.0852 no . 2_656 H16 C15 3.5923 no . 2_656 H16 C20 3.4682 no . 2_646 H16 H7 2.7754 no . 1_565 H16 H14 2.7216 no . 2_656 H16 H16 3.4592 no . 2_656 H16 H20A 3.5840 no . 2_646 H16 H20A 2.9946 no . 2_656 H16 H20B 3.0784 no . 2_646 H16 H20C 3.1942 no . 2_646 H17 F3 2.8463 no . 1_565 H17 N2 3.2984 no . 1_565 H17 C20 2.9939 no . 2_646 H17 H2 3.3544 no . 1_565 H17 H3 3.4539 no . 1_565 H17 H7 3.5226 no . 1_565 H17 H20A 2.5433 no . 2_646 H17 H20B 3.1914 no . 2_646 H17 H20C 2.7795 no . 2_646 H19A C9 3.1587 no . 1_545 H19A C10 2.7104 no . 1_545 H19A C11 3.1730 no . 1_545 H19A C14 3.3461 no . 1_545 H19A C15 2.8166 no . 1_545 H19A C16 3.3438 no . 1_545 H19A C19 3.4528 no . 2_657 H19A H9 3.4057 no . 2_657 H19A H11 3.4024 no . 2_647 H19A H19A 3.0221 no . 2_657 H19A H19B 3.0470 no . 2_657 H19B C9 3.3854 no . 2_657 H19B C11 3.2590 no . 2_647 H19B C12 3.0844 no . 2_647 H19B H9 2.4733 no . 2_657 H19B H11 3.3124 no . 2_647 H19B H11 3.0215 no . 2_657 H19B H12 3.0276 no . 2_647 H19B H19A 3.0470 no . 2_657 H19B H19B 3.3363 no . 2_657 H19C O5 3.5601 no . 4_647 H19C O6 2.9443 no . 1_545 H19C C8 3.5432 no . 1_545 H19C C9 3.5914 no . 1_545 H19C C11 2.9942 no . 2_647 H19C C12 3.1743 no . 2_647 H19C H11 2.5842 no . 2_647 H19C H12 2.9356 no . 2_647 H20A F1 2.8889 no . 2_666 H20A F2 3.5719 no . 3_465 H20A F3 3.0169 no . 2_666 H20A C17 3.0813 no . 2_666 H20A C18 3.5470 no . 2_666 H20A H7 3.3700 no . 2_666 H20A H16 2.9946 no . 2_656 H20A H16 3.5840 no . 2_666 H20A H17 2.5433 no . 2_666 H20B C9 3.3761 no . 1_565 H20B C10 2.8834 no . 1_565 H20B C11 3.3739 no . 1_565 H20B C14 3.3220 no . 1_565 H20B C15 2.8478 no . 1_565 H20B C16 3.3216 no . 1_565 H20B C16 3.4192 no . 2_666 H20B C17 3.4778 no . 2_666 H20B H16 3.0784 no . 2_666 H20B H17 3.1914 no . 2_666 H20C F1 3.1895 no . 2_666 H20C F2 2.6279 no . 3_465 H20C F3 2.7587 no . 2_676 H20C C17 3.4403 no . 2_666 H20C H4B 3.2195 no . 3_465 H20C H16 3.1942 no . 2_666 H20C H17 2.7795 no . 2_666 #============================================================================== loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_distance_DA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_angle_DHA _geom_hbond_publ_flag N2 H2 O6 . . 1_545 2.932(9) 0.980 2.07(7) 145(6) no #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #============================================================================== _database_code_depnum_ccdc_archive 'CCDC 956169' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_20 _chemical_formula_sum 'C18 H17 F3 N2 O3' _chemical_formula_moiety 'C18 H17 F3 N2 O3' _chemical_formula_weight 366.34 _chemical_melting_point ? _chemical_absolute_configuration syn #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21 1' _symmetry_space_group_name_Hall 'P 2yb' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,1/2+Y,-Z #------------------------------------------------------------------------------ _cell_length_a 11.641(9) _cell_length_b 6.185(4) _cell_length_c 11.974(9) _cell_angle_alpha 90.0000 _cell_angle_beta 104.942(18) _cell_angle_gamma 90.0000 _cell_volume 833.0(10) _cell_formula_units_Z 2 _cell_measurement_reflns_used 2740 _cell_measurement_theta_min 3.29 _cell_measurement_theta_max 25.35 _cell_measurement_temperature 93 #------------------------------------------------------------------------------ _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.100 _exptl_crystal_size_mid 0.050 _exptl_crystal_size_min 0.010 _exptl_crystal_density_diffrn 1.460 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 380.00 _exptl_absorpt_coefficient_mu 0.122 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'REQAB (Rigaku, 1998)' _exptl_absorpt_correction_T_min 0.656 _exptl_absorpt_correction_T_max 0.999 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 93 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_measurement_device_type 'Rigaku Mercury70' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 14.629 _diffrn_reflns_number 5186 _diffrn_reflns_av_R_equivalents 0.0512 _diffrn_reflns_theta_min 2.176 _diffrn_reflns_theta_max 25.298 _diffrn_reflns_theta_full 25.000 _diffrn_measured_fraction_theta_max 0.989 _diffrn_measured_fraction_theta_full 0.990 _diffrn_reflns_Laue_measured_fraction_max 0.989 _diffrn_reflns_Laue_measured_fraction_full 0.990 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 14 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 2752 _reflns_number_gt 2165 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0642 _refine_ls_wR_factor_ref 0.1797 _refine_ls_number_restraints 2 _refine_ls_hydrogen_treatment mixed _refine_ls_number_reflns 2752 _refine_ls_number_parameters 239 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0948P)^2^+0.0092P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.004 _refine_diff_density_max 0.280 _refine_diff_density_min -0.330 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Parsons and Flack (2004), Acta Cryst. A60, s61' _refine_ls_abs_structure_Flack 0.2(9) 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 for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; F F 0.0171 0.0103 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; N N 0.0061 0.0033 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.0106 0.0060 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 1.3786(4) 1.3556(9) 0.9453(4) 0.0572(12) Uani 1.0 2 d . . . F2 F 1.3796(3) 1.0267(7) 1.0092(4) 0.0480(11) Uani 1.0 2 d . . . F3 F 1.4476(3) 1.2880(7) 1.1271(4) 0.0519(11) Uani 1.0 2 d . . . O5 O 1.1389(4) 0.7666(8) 1.1368(4) 0.0401(11) Uani 1.0 2 d . . . O6 O 1.0636(4) 0.6429(8) 0.9085(4) 0.0359(10) Uani 1.0 2 d . . . O13 O 0.4822(4) 0.8892(7) 0.3247(4) 0.0379(11) Uani 1.0 2 d . . . N1 N 1.1233(4) 0.9793(8) 0.9728(4) 0.0280(11) Uani 1.0 2 d . . . N2 N 1.1513(5) 1.1956(8) 0.9457(4) 0.0314(12) Uani 1.0 2 d . . . C3 C 1.2390(5) 1.2707(11) 1.0505(5) 0.0327(13) Uani 1.0 2 d . . . C4 C 1.2181(6) 1.1353(11) 1.1506(5) 0.0342(14) Uani 1.0 2 d . . . C5 C 1.1547(6) 0.9388(10) 1.0919(5) 0.0327(14) Uani 1.0 2 d . . . C6 C 1.0984(5) 0.8192(10) 0.8866(5) 0.0285(13) Uani 1.0 2 d . . . C7 C 1.1204(5) 0.8738(11) 0.7695(5) 0.0321(14) Uani 1.0 2 d . . . C8 C 1.0037(5) 0.8372(10) 0.6772(5) 0.0283(13) Uani 1.0 2 d . . . C9 C 0.9182(5) 0.9938(11) 0.6553(5) 0.0303(13) Uani 1.0 2 d . . . C10 C 0.8072(6) 0.9659(11) 0.5721(5) 0.0315(13) Uani 1.0 2 d . . . C11 C 0.7159(6) 1.1259(12) 0.5514(5) 0.0363(14) Uani 1.0 2 d . . . C12 C 0.6106(6) 1.0939(11) 0.4697(5) 0.0356(15) Uani 1.0 2 d . . . C13 C 0.5923(5) 0.9000(10) 0.4039(5) 0.0312(14) Uani 1.0 2 d . . . C14 C 0.6772(5) 0.7411(11) 0.4209(5) 0.0336(14) Uani 1.0 2 d . . . C15 C 0.7874(5) 0.7714(10) 0.5061(5) 0.0287(13) Uani 1.0 2 d . . . C16 C 0.8773(5) 0.6113(11) 0.5295(5) 0.0331(14) Uani 1.0 2 d . . . C17 C 0.9817(5) 0.6426(11) 0.6124(5) 0.0315(13) Uani 1.0 2 d . . . C18 C 1.3603(6) 1.2389(13) 1.0328(6) 0.0426(16) Uani 1.0 2 d . . . C19 C 1.2248(5) 0.7307(12) 0.7567(5) 0.0380(15) Uani 1.0 2 d . . . C20 C 0.4603(6) 0.6956(12) 0.2552(6) 0.0425(16) Uani 1.0 2 d . . . H2 H 1.078(4) 1.281(10) 0.928(5) 0.039(18) Uiso 1.0 2 d . . . H3 H 1.2257 1.4272 1.0640 0.0392 Uiso 1.0 2 calc R . . H4A H 1.2944 1.0956 1.2055 0.0411 Uiso 1.0 2 calc R . . H4B H 1.1684 1.2146 1.1927 0.0411 Uiso 1.0 2 calc R . . H7 H 1.1437 1.0293 0.7689 0.0385 Uiso 1.0 2 calc R . . H9 H 0.9333 1.1259 0.6970 0.0364 Uiso 1.0 2 calc R . . H11 H 0.7282 1.2563 0.5947 0.0435 Uiso 1.0 2 calc R . . H12 H 0.5502 1.2010 0.4572 0.0427 Uiso 1.0 2 calc R . . H14 H 0.6630 0.6120 0.3765 0.0404 Uiso 1.0 2 calc R . . H16 H 0.8650 0.4799 0.4871 0.0398 Uiso 1.0 2 calc R . . H17 H 1.0404 0.5322 0.6267 0.0377 Uiso 1.0 2 calc R . . H19A H 1.2310 0.7368 0.6766 0.0456 Uiso 1.0 2 calc R . . H19B H 1.2109 0.5810 0.7766 0.0456 Uiso 1.0 2 calc R . . H19C H 1.2989 0.7834 0.8086 0.0456 Uiso 1.0 2 calc R . . H20A H 0.3782 0.6966 0.2072 0.0510 Uiso 1.0 2 calc R . . H20B H 0.4727 0.5685 0.3058 0.0510 Uiso 1.0 2 calc R . . H20C H 0.5152 0.6902 0.2055 0.0510 Uiso 1.0 2 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 F1 0.047(3) 0.070(3) 0.055(3) -0.013(2) 0.014(2) 0.010(3) F2 0.037(2) 0.051(3) 0.056(3) 0.0047(19) 0.0120(18) -0.013(2) F3 0.0342(19) 0.061(3) 0.054(3) -0.0075(19) 0.0006(18) -0.012(2) O5 0.043(3) 0.045(3) 0.031(3) -0.003(2) 0.0067(19) 0.009(2) O6 0.040(3) 0.036(3) 0.031(2) -0.004(2) 0.0079(18) -0.0009(19) O13 0.032(3) 0.043(3) 0.034(3) 0.001(2) 0.0008(18) -0.006(2) N1 0.033(3) 0.028(3) 0.021(3) 0.003(3) 0.005(2) 0.003(2) N2 0.032(3) 0.032(3) 0.028(3) -0.006(3) 0.004(2) -0.000(2) C3 0.032(3) 0.031(4) 0.033(3) -0.002(3) 0.006(3) -0.003(3) C4 0.030(3) 0.039(4) 0.031(3) 0.000(3) 0.003(3) -0.003(3) C5 0.029(3) 0.040(4) 0.030(3) 0.002(3) 0.009(3) -0.002(3) C6 0.027(3) 0.032(4) 0.025(3) 0.001(3) 0.005(3) 0.000(3) C7 0.034(3) 0.038(4) 0.022(3) -0.001(3) 0.004(3) 0.003(3) C8 0.032(3) 0.029(4) 0.023(3) -0.002(3) 0.005(3) 0.002(3) C9 0.033(4) 0.032(4) 0.025(3) -0.002(3) 0.006(3) -0.003(3) C10 0.036(3) 0.034(4) 0.025(3) -0.000(3) 0.010(3) -0.001(3) C11 0.040(4) 0.040(4) 0.028(3) -0.004(3) 0.008(3) -0.001(3) C12 0.041(4) 0.035(4) 0.032(3) 0.005(3) 0.010(3) 0.004(3) C13 0.029(3) 0.040(4) 0.024(3) 0.004(3) 0.006(3) -0.002(3) C14 0.032(3) 0.037(4) 0.028(3) -0.000(3) 0.001(3) 0.001(3) C15 0.029(3) 0.034(4) 0.025(3) -0.000(3) 0.010(3) -0.001(3) C16 0.032(3) 0.034(4) 0.033(3) 0.001(3) 0.007(3) -0.000(3) C17 0.029(3) 0.032(4) 0.034(3) 0.001(3) 0.009(3) -0.002(3) C18 0.032(4) 0.050(5) 0.042(4) 0.001(4) 0.004(3) 0.004(4) C19 0.033(3) 0.052(4) 0.029(3) 0.001(3) 0.009(3) -0.003(3) C20 0.039(4) 0.048(5) 0.034(3) -0.001(3) -0.001(3) -0.005(3) #============================================================================== _computing_data_collection 'CrystalClear-SM Expert 2.0 rc13 (Rigaku, 2009)' _computing_cell_refinement 'CrystalClear-SM Expert 2.0 rc13' _computing_data_reduction 'CrystalClear-SM Expert 2.0 rc13' _computing_structure_solution 'SIR2004 (Burla, et al., 2005)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 F1 C18 1.334(9) yes . . F2 C18 1.373(9) yes . . F3 C18 1.345(7) yes . . O5 C5 1.228(8) yes . . O6 C6 1.216(8) yes . . O13 C13 1.385(7) yes . . O13 C20 1.443(8) yes . . N1 N2 1.434(7) yes . . N1 C5 1.400(8) yes . . N1 C6 1.406(8) yes . . N2 C3 1.475(7) yes . . C3 C4 1.531(9) yes . . C3 C18 1.495(10) yes . . C4 C5 1.499(9) yes . . C6 C7 1.527(9) yes . . C7 C8 1.531(7) yes . . C7 C19 1.543(9) yes . . C8 C9 1.365(9) yes . . C8 C17 1.419(9) yes . . C9 C10 1.424(8) yes . . C10 C11 1.427(9) yes . . C10 C15 1.425(9) yes . . C11 C12 1.371(8) yes . . C12 C13 1.421(9) yes . . C13 C14 1.371(9) yes . . C14 C15 1.431(7) yes . . C15 C16 1.415(9) yes . . C16 C17 1.371(8) yes . . N2 H2 0.98(5) no . . C3 H3 1.000 no . . C4 H4A 0.990 no . . C4 H4B 0.990 no . . C7 H7 1.000 no . . C9 H9 0.950 no . . C11 H11 0.950 no . . C12 H12 0.950 no . . C14 H14 0.950 no . . C16 H16 0.950 no . . C17 H17 0.950 no . . C19 H19A 0.980 no . . C19 H19B 0.980 no . . C19 H19C 0.980 no . . C20 H20A 0.980 no . . C20 H20B 0.980 no . . C20 H20C 0.980 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C13 O13 C20 115.4(5) yes . . . N2 N1 C5 112.5(5) yes . . . N2 N1 C6 120.4(5) yes . . . C5 N1 C6 124.9(5) yes . . . N1 N2 C3 104.4(5) yes . . . N2 C3 C4 106.2(5) yes . . . N2 C3 C18 108.0(6) yes . . . C4 C3 C18 112.7(5) yes . . . C3 C4 C5 103.6(5) yes . . . O5 C5 N1 124.8(6) yes . . . O5 C5 C4 127.5(5) yes . . . N1 C5 C4 107.5(5) yes . . . O6 C6 N1 119.4(6) yes . . . O6 C6 C7 122.7(6) yes . . . N1 C6 C7 117.9(6) yes . . . C6 C7 C8 107.6(5) yes . . . C6 C7 C19 106.7(5) yes . . . C8 C7 C19 114.8(5) yes . . . C7 C8 C9 120.1(6) yes . . . C7 C8 C17 121.4(5) yes . . . C9 C8 C17 118.5(5) yes . . . C8 C9 C10 122.3(6) yes . . . C9 C10 C11 122.6(6) yes . . . C9 C10 C15 118.6(6) yes . . . C11 C10 C15 118.8(5) yes . . . C10 C11 C12 120.9(6) yes . . . C11 C12 C13 119.8(6) yes . . . O13 C13 C12 113.6(6) yes . . . O13 C13 C14 124.9(6) yes . . . C12 C13 C14 121.5(5) yes . . . C13 C14 C15 119.4(6) yes . . . C10 C15 C14 119.5(6) yes . . . C10 C15 C16 118.4(5) yes . . . C14 C15 C16 122.0(6) yes . . . C15 C16 C17 121.1(6) yes . . . C8 C17 C16 121.1(6) yes . . . F1 C18 F2 106.8(6) yes . . . F1 C18 F3 107.4(6) yes . . . F1 C18 C3 112.9(6) yes . . . F2 C18 F3 105.1(5) yes . . . F2 C18 C3 111.4(6) yes . . . F3 C18 C3 112.8(6) yes . . . N1 N2 H2 108(4) no . . . C3 N2 H2 113(4) no . . . N2 C3 H3 109.941 no . . . C4 C3 H3 109.948 no . . . C18 C3 H3 109.943 no . . . C3 C4 H4A 111.048 no . . . C3 C4 H4B 111.047 no . . . C5 C4 H4A 111.044 no . . . C5 C4 H4B 111.045 no . . . H4A C4 H4B 109.023 no . . . C6 C7 H7 109.211 no . . . C8 C7 H7 109.205 no . . . C19 C7 H7 109.208 no . . . C8 C9 H9 118.870 no . . . C10 C9 H9 118.872 no . . . C10 C11 H11 119.559 no . . . C12 C11 H11 119.554 no . . . C11 C12 H12 120.118 no . . . C13 C12 H12 120.121 no . . . C13 C14 H14 120.278 no . . . C15 C14 H14 120.281 no . . . C15 C16 H16 119.437 no . . . C17 C16 H16 119.438 no . . . C8 C17 H17 119.444 no . . . C16 C17 H17 119.434 no . . . C7 C19 H19A 109.473 no . . . C7 C19 H19B 109.477 no . . . C7 C19 H19C 109.472 no . . . H19A C19 H19B 109.469 no . . . H19A C19 H19C 109.467 no . . . H19B C19 H19C 109.469 no . . . O13 C20 H20A 109.473 no . . . O13 C20 H20B 109.471 no . . . O13 C20 H20C 109.465 no . . . H20A C20 H20B 109.475 no . . . H20A C20 H20C 109.474 no . . . H20B C20 H20C 109.469 no . . . 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C20 O13 C13 C12 179.4(5) no . . . . C20 O13 C13 C14 -1.5(9) no . . . . N2 N1 C5 O5 179.3(5) no . . . . N2 N1 C5 C4 -4.9(7) no . . . . C5 N1 N2 C3 18.6(6) no . . . . N2 N1 C6 O6 -172.8(5) no . . . . N2 N1 C6 C7 9.0(7) no . . . . C6 N1 N2 C3 -145.4(5) no . . . . C5 N1 C6 O6 25.3(8) no . . . . C5 N1 C6 C7 -152.9(5) no . . . . C6 N1 C5 O5 -17.5(10) no . . . . C6 N1 C5 C4 158.2(5) no . . . . N1 N2 C3 C4 -24.2(6) no . . . . N1 N2 C3 C18 96.9(5) no . . . . N2 C3 C4 C5 21.4(6) no . . . . N2 C3 C18 F1 62.6(7) no . . . . N2 C3 C18 F2 -57.5(7) no . . . . N2 C3 C18 F3 -175.5(5) no . . . . C4 C3 C18 F1 179.6(5) no . . . . C4 C3 C18 F2 59.5(7) no . . . . C4 C3 C18 F3 -58.5(8) no . . . . C18 C3 C4 C5 -96.7(6) no . . . . C3 C4 C5 O5 165.3(6) no . . . . C3 C4 C5 N1 -10.3(6) no . . . . O6 C6 C7 C8 58.1(7) no . . . . O6 C6 C7 C19 -65.6(7) no . . . . N1 C6 C7 C8 -123.8(5) no . . . . N1 C6 C7 C19 112.6(5) no . . . . C6 C7 C8 C9 82.7(7) no . . . . C6 C7 C8 C17 -97.6(6) no . . . . C19 C7 C8 C9 -158.7(5) no . . . . C19 C7 C8 C17 21.0(8) no . . . . C7 C8 C9 C10 -178.7(5) no . . . . C7 C8 C17 C16 -179.7(5) no . . . . C9 C8 C17 C16 -0.0(9) no . . . . C17 C8 C9 C10 1.6(9) no . . . . C8 C9 C10 C11 177.9(6) no . . . . C8 C9 C10 C15 -2.9(9) no . . . . C9 C10 C11 C12 179.4(6) no . . . . C9 C10 C15 C14 -179.1(5) no . . . . C9 C10 C15 C16 2.4(9) no . . . . C11 C10 C15 C14 0.1(9) no . . . . C11 C10 C15 C16 -178.3(5) no . . . . C15 C10 C11 C12 0.1(9) no . . . . C10 C11 C12 C13 -0.6(10) no . . . . C11 C12 C13 O13 180.0(6) no . . . . C11 C12 C13 C14 0.9(10) no . . . . O13 C13 C14 C15 -179.6(5) no . . . . C12 C13 C14 C15 -0.6(10) no . . . . C13 C14 C15 C10 0.1(9) no . . . . C13 C14 C15 C16 178.5(6) no . . . . C10 C15 C16 C17 -0.9(9) no . . . . C14 C15 C16 C17 -179.3(6) no . . . . C15 C16 C17 C8 -0.3(10) no . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 F1 N2 2.827(7) no . . F2 N1 2.917(7) no . . F2 N2 2.773(7) no . . F2 C4 2.914(8) no . . F2 C5 3.076(8) no . . F2 C6 3.469(7) no . . F2 C19 3.596(8) no . . F3 C4 2.915(8) no . . O5 O6 2.755(6) no . . O5 N2 3.531(7) no . . O5 C3 3.573(9) no . . O5 C6 2.928(8) no . . O6 N2 3.563(7) no . . O6 C5 2.845(7) no . . O6 C8 2.933(7) no . . O6 C17 3.426(7) no . . O6 C19 2.980(9) no . . N1 C8 3.563(7) no . . N1 C18 3.113(9) no . . N1 C19 3.469(9) no . . N2 C7 2.855(8) no . . C3 C6 3.560(9) no . . C5 C18 3.248(10) no . . C6 C9 3.201(8) no . . C6 C17 3.394(8) no . . C8 C15 2.836(7) no . . C9 C16 2.779(9) no . . C10 C13 2.808(8) no . . C10 C17 2.802(9) no . . C11 C14 2.818(10) no . . C12 C15 2.818(9) no . . C14 C20 2.794(8) no . . C17 C19 2.961(8) no . . F1 F2 2.924(6) no . 2_857 F1 F3 3.592(7) no . 2_857 F1 C19 3.406(8) no . 1_565 F1 C20 3.546(9) no . 2_756 F2 F1 2.924(6) no . 2_847 F2 F3 3.254(7) no . 2_847 F2 C20 3.511(8) no . 1_656 F3 F1 3.592(7) no . 2_847 F3 F2 3.254(7) no . 2_857 F3 O13 3.370(7) no . 1_656 F3 C20 2.935(9) no . 1_666 O5 O6 3.257(7) no . 2_757 O5 N1 3.482(7) no . 2_747 O5 N2 3.295(7) no . 2_747 O5 C3 3.529(9) no . 1_545 O5 C9 3.216(8) no . 2_747 O6 O5 3.257(7) no . 2_747 O6 N1 3.061(7) no . 2_747 O6 N2 2.943(7) no . 1_545 O6 N2 3.415(8) no . 2_747 O6 C3 3.251(8) no . 1_545 O6 C4 3.172(8) no . 2_747 O6 C5 2.837(8) no . 2_747 O13 F3 3.370(7) no . 1_454 O13 C4 3.579(7) no . 1_454 O13 C11 3.455(9) no . 2_646 O13 C12 3.455(9) no . 2_646 N1 O5 3.482(7) no . 2_757 N1 O6 3.061(7) no . 2_757 N2 O5 3.295(7) no . 2_757 N2 O6 2.943(7) no . 1_565 N2 O6 3.415(8) no . 2_757 C3 O5 3.529(9) no . 1_565 C3 O6 3.251(8) no . 1_565 C4 O6 3.172(8) no . 2_757 C4 O13 3.579(7) no . 1_656 C5 O6 2.837(8) no . 2_757 C8 C16 3.563(9) no . 2_756 C9 O5 3.216(8) no . 2_757 C11 O13 3.455(9) no . 2_656 C11 C16 3.587(10) no . 1_565 C11 C20 3.494(10) no . 2_656 C12 O13 3.455(9) no . 2_656 C16 C8 3.563(9) no . 2_746 C16 C11 3.587(10) no . 1_545 C19 F1 3.406(8) no . 1_545 C20 F1 3.546(9) no . 2_746 C20 F2 3.511(8) no . 1_454 C20 F3 2.935(9) no . 1_444 C20 C11 3.494(10) no . 2_646 F1 H2 3.48(5) no . . F1 H3 2.5866 no . . F2 H3 3.2219 no . . F2 H4A 2.8090 no . . F2 H7 3.4271 no . . F2 H19C 2.7847 no . . F3 H3 2.6412 no . . F3 H4A 2.5181 no . . F3 H4B 3.5638 no . . O5 H4A 2.7073 no . . O5 H4B 2.8508 no . . O6 H7 3.1906 no . . O6 H17 3.3855 no . . O6 H19B 2.6411 no . . O6 H19C 3.3736 no . . O13 H12 2.4926 no . . O13 H14 2.6609 no . . N1 H3 3.1018 no . . N1 H4A 3.0641 no . . N1 H4B 2.9353 no . . N1 H7 2.5323 no . . N1 H9 3.5853 no . . N1 H19C 3.4042 no . . N2 H4A 3.1883 no . . N2 H4B 2.9157 no . . N2 H7 2.3344 no . . N2 H9 3.4053 no . . C3 H7 3.5923 no . . C4 H2 2.88(6) no . . C5 H2 2.87(6) no . . C5 H3 3.1723 no . . C6 H2 2.92(6) no . . C6 H9 3.1939 no . . C6 H17 3.4945 no . . C6 H19A 3.3107 no . . C6 H19B 2.5505 no . . C6 H19C 2.7371 no . . C7 H2 3.27(6) no . . C7 H9 2.6376 no . . C7 H17 2.7265 no . . C8 H16 3.2834 no . . C8 H19A 2.7190 no . . C8 H19B 2.8745 no . . C8 H19C 3.4069 no . . C9 H7 2.6359 no . . C9 H11 2.6887 no . . C9 H17 3.2474 no . . C10 H12 3.2924 no . . C10 H14 3.3271 no . . C10 H16 3.2984 no . . C11 H9 2.6773 no . . C12 H14 3.2941 no . . C13 H11 3.2736 no . . C13 H20A 3.2113 no . . C13 H20B 2.5846 no . . C13 H20C 2.6522 no . . C14 H12 3.2860 no . . C14 H16 2.6688 no . . C14 H20B 2.6489 no . . C14 H20C 2.7931 no . . C15 H9 3.3030 no . . C15 H11 3.3124 no . . C15 H17 3.2794 no . . C16 H14 2.6875 no . . C17 H7 3.3113 no . . C17 H9 3.2518 no . . C17 H19A 2.8630 no . . C17 H19B 2.9022 no . . C18 H2 3.21(4) no . . C18 H4A 2.5440 no . . C18 H4B 3.2999 no . . C19 H17 2.6104 no . . C20 H14 2.4849 no . . H2 H3 2.2295 no . . H2 H4B 3.0962 no . . H2 H7 2.7219 no . . H2 H9 3.0048 no . . H3 H4A 2.6491 no . . H3 H4B 2.2540 no . . H7 H9 2.4520 no . . H7 H17 3.5698 no . . H7 H19A 2.4706 no . . H7 H19B 2.8756 no . . H7 H19C 2.3152 no . . H9 H11 2.5184 no . . H11 H12 2.3158 no . . H14 H16 2.5187 no . . H14 H20A 3.4504 no . . H14 H20B 2.1748 no . . H14 H20C 2.3600 no . . H16 H17 2.3045 no . . H17 H19A 2.4888 no . . H17 H19B 2.3272 no . . H17 H19C 3.5824 no . . F1 H19B 2.7930 no . 1_565 F1 H19C 3.1239 no . 1_565 F1 H20C 2.6422 no . 2_756 F2 H20A 3.1314 no . 1_656 F2 H20C 3.2301 no . 1_656 F2 H20C 3.2794 no . 2_756 F3 H19C 2.8512 no . 2_857 F3 H20A 2.8911 no . 1_666 F3 H20B 2.7111 no . 1_666 F3 H20C 2.7034 no . 1_666 O5 H2 2.44(4) no . 2_747 O5 H3 2.5771 no . 1_545 O5 H4B 3.4794 no . 1_545 O5 H9 2.5074 no . 2_747 O5 H11 3.1893 no . 2_747 O5 H20A 2.7298 no . 1_656 O6 H2 2.25(6) no . 1_545 O6 H2 2.99(6) no . 2_747 O6 H3 2.6451 no . 1_545 O6 H4B 2.6970 no . 2_747 O13 H4A 2.6148 no . 1_454 O13 H11 2.9700 no . 2_646 O13 H12 2.9707 no . 2_646 N1 H2 3.13(6) no . 2_747 N2 H19B 3.3148 no . 1_565 C3 H20A 3.3939 no . 1_666 C4 H20A 3.2626 no . 1_656 C5 H2 2.83(5) no . 2_747 C5 H3 3.3089 no . 1_545 C5 H9 3.5388 no . 2_747 C5 H20A 3.0111 no . 1_656 C6 H2 3.38(6) no . 1_545 C6 H2 3.40(6) no . 2_747 C6 H3 3.3109 no . 1_545 C6 H4B 3.0743 no . 2_747 C7 H16 3.1885 no . 2_756 C8 H4B 2.9370 no . 2_747 C8 H16 2.9218 no . 2_756 C9 H4B 2.8737 no . 2_747 C9 H16 3.5829 no . 1_565 C9 H16 3.3917 no . 2_756 C9 H17 3.5390 no . 2_756 C10 H4B 3.1646 no . 2_747 C10 H16 3.4563 no . 1_565 C10 H17 3.3396 no . 2_756 C10 H19A 3.3455 no . 2_756 C11 H16 3.0143 no . 1_565 C11 H19A 3.0292 no . 2_756 C11 H20A 3.3745 no . 2_656 C11 H20B 3.1320 no . 2_656 C12 H12 3.3200 no . 2_646 C12 H14 3.4985 no . 1_565 C12 H19A 2.9861 no . 2_756 C12 H20B 3.0886 no . 2_656 C13 H12 2.9084 no . 2_646 C13 H19A 3.2439 no . 2_756 C14 H12 3.3456 no . 2_646 C14 H19A 3.5890 no . 2_746 C14 H19A 3.5424 no . 2_756 C15 H4B 3.5262 no . 2_747 C15 H11 3.4829 no . 1_545 C15 H17 3.2844 no . 2_756 C15 H19A 3.5886 no . 2_756 C16 H4B 3.5587 no . 2_747 C16 H7 3.5547 no . 2_746 C16 H9 3.5759 no . 1_545 C16 H11 3.0236 no . 1_545 C16 H17 3.4807 no . 2_756 C16 H19A 3.3827 no . 2_746 C17 H4B 3.2869 no . 2_747 C17 H9 3.4430 no . 1_545 C17 H16 3.1703 no . 2_756 C18 H20A 3.4926 no . 1_666 C18 H20C 3.5293 no . 2_756 C19 H14 3.2992 no . 2_756 C19 H16 3.2267 no . 2_756 C20 H3 3.4971 no . 1_444 C20 H4A 3.1007 no . 1_454 C20 H11 3.1968 no . 2_646 C20 H12 3.4778 no . 2_646 H2 O5 2.44(4) no . 2_757 H2 O6 2.25(6) no . 1_565 H2 O6 2.99(6) no . 2_757 H2 N1 3.13(6) no . 2_757 H2 C5 2.83(5) no . 2_757 H2 C6 3.38(6) no . 1_565 H2 C6 3.40(6) no . 2_757 H2 H19B 3.2516 no . 1_565 H3 O5 2.5771 no . 1_565 H3 O6 2.6451 no . 1_565 H3 C5 3.3089 no . 1_565 H3 C6 3.3109 no . 1_565 H3 C20 3.4971 no . 1_666 H3 H19B 3.5314 no . 1_565 H3 H20A 2.7013 no . 1_666 H4A O13 2.6148 no . 1_656 H4A C20 3.1007 no . 1_656 H4A H11 3.2437 no . 2_747 H4A H20A 2.6521 no . 1_656 H4A H20C 3.5911 no . 1_656 H4B O5 3.4794 no . 1_565 H4B O6 2.6970 no . 2_757 H4B C6 3.0743 no . 2_757 H4B C8 2.9370 no . 2_757 H4B C9 2.8737 no . 2_757 H4B C10 3.1646 no . 2_757 H4B C15 3.5262 no . 2_757 H4B C16 3.5587 no . 2_757 H4B C17 3.2869 no . 2_757 H4B H9 3.2287 no . 2_757 H7 C16 3.5547 no . 2_756 H7 H14 3.2211 no . 2_756 H7 H16 3.0559 no . 2_756 H7 H19B 3.4973 no . 1_565 H9 O5 2.5074 no . 2_757 H9 C5 3.5388 no . 2_757 H9 C16 3.5759 no . 1_565 H9 C17 3.4430 no . 1_565 H9 H4B 3.2287 no . 2_747 H9 H16 3.2730 no . 1_565 H9 H17 3.0204 no . 1_565 H11 O5 3.1893 no . 2_757 H11 O13 2.9700 no . 2_656 H11 C15 3.4829 no . 1_565 H11 C16 3.0236 no . 1_565 H11 C20 3.1968 no . 2_656 H11 H4A 3.2437 no . 2_757 H11 H14 3.3501 no . 1_565 H11 H16 2.6771 no . 1_565 H11 H19A 3.4050 no . 2_756 H11 H20A 2.9689 no . 2_656 H11 H20B 3.1103 no . 2_656 H12 O13 2.9707 no . 2_656 H12 C12 3.3200 no . 2_656 H12 C13 2.9084 no . 2_656 H12 C14 3.3456 no . 2_656 H12 C20 3.4778 no . 2_656 H12 H12 3.5495 no . 2_646 H12 H12 3.5495 no . 2_656 H12 H14 3.1267 no . 1_565 H12 H19A 3.3484 no . 2_756 H12 H20B 2.9025 no . 1_565 H12 H20B 3.0316 no . 2_656 H14 C12 3.4985 no . 1_545 H14 C19 3.2992 no . 2_746 H14 H7 3.2211 no . 2_746 H14 H11 3.3501 no . 1_545 H14 H12 3.1267 no . 1_545 H14 H19A 2.7785 no . 2_746 H14 H19C 3.1218 no . 2_746 H16 C7 3.1885 no . 2_746 H16 C8 2.9218 no . 2_746 H16 C9 3.5829 no . 1_545 H16 C9 3.3917 no . 2_746 H16 C10 3.4563 no . 1_545 H16 C11 3.0143 no . 1_545 H16 C17 3.1703 no . 2_746 H16 C19 3.2267 no . 2_746 H16 H7 3.0559 no . 2_746 H16 H9 3.2730 no . 1_545 H16 H11 2.6771 no . 1_545 H16 H17 3.3924 no . 2_746 H16 H19A 2.4940 no . 2_746 H17 C9 3.5390 no . 2_746 H17 C10 3.3396 no . 2_746 H17 C15 3.2844 no . 2_746 H17 C16 3.4807 no . 2_746 H17 H9 3.0204 no . 1_545 H17 H16 3.3924 no . 2_756 H19A C10 3.3455 no . 2_746 H19A C11 3.0292 no . 2_746 H19A C12 2.9861 no . 2_746 H19A C13 3.2439 no . 2_746 H19A C14 3.5424 no . 2_746 H19A C14 3.5890 no . 2_756 H19A C15 3.5886 no . 2_746 H19A C16 3.3827 no . 2_756 H19A H11 3.4050 no . 2_746 H19A H12 3.3484 no . 2_746 H19A H14 2.7785 no . 2_756 H19A H16 2.4940 no . 2_756 H19B F1 2.7930 no . 1_545 H19B N2 3.3148 no . 1_545 H19B H2 3.2516 no . 1_545 H19B H3 3.5314 no . 1_545 H19B H7 3.4973 no . 1_545 H19C F1 3.1239 no . 1_545 H19C F3 2.8512 no . 2_847 H19C H14 3.1218 no . 2_756 H19C H20C 3.3508 no . 2_756 H20A F2 3.1314 no . 1_454 H20A F3 2.8911 no . 1_444 H20A O5 2.7298 no . 1_454 H20A C3 3.3939 no . 1_444 H20A C4 3.2626 no . 1_454 H20A C5 3.0111 no . 1_454 H20A C11 3.3745 no . 2_646 H20A C18 3.4926 no . 1_444 H20A H3 2.7013 no . 1_444 H20A H4A 2.6521 no . 1_454 H20A H11 2.9689 no . 2_646 H20B F3 2.7111 no . 1_444 H20B C11 3.1320 no . 2_646 H20B C12 3.0886 no . 2_646 H20B H11 3.1103 no . 2_646 H20B H12 2.9025 no . 1_545 H20B H12 3.0316 no . 2_646 H20C F1 2.6422 no . 2_746 H20C F2 3.2301 no . 1_454 H20C F2 3.2794 no . 2_746 H20C F3 2.7034 no . 1_444 H20C C18 3.5293 no . 2_746 H20C H4A 3.5911 no . 1_454 H20C H19C 3.3508 no . 2_746 #============================================================================== loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_distance_DA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_angle_DHA _geom_hbond_publ_flag N2 H2 O6 . . 1_565 2.943(7) 0.979 2.25(5) 127(4) no #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #============================================================================== _database_code_depnum_ccdc_archive 'CCDC 956170' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_21 # CHEMICAL DATA _chemical_formula_sum 'C19 H22 N2 O3' _chemical_formula_moiety 'C19 H22 N2 O3' _chemical_formula_weight 326.39 _chemical_melting_point ? _chemical_absolute_configuration syn #============================================================================== # CRYSTAL DATA _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 1/2+X,1/2-Y,-Z 3 -X,1/2+Y,1/2-Z 4 1/2-X,-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 7.735(2) _cell_length_b 14.242(4) _cell_length_c 16.353(4) _cell_angle_alpha 90.0000 _cell_angle_beta 90.0000 _cell_angle_gamma 90.0000 _cell_volume 1801.4(8) _cell_formula_units_Z 4 _cell_measurement_reflns_used 6355 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 25.35 _cell_measurement_temperature 93 #------------------------------------------------------------------------------ _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.240 _exptl_crystal_size_mid 0.050 _exptl_crystal_size_min 0.030 _exptl_crystal_density_diffrn 1.203 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696.00 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'REQAB (Rigaku, 1998)' _exptl_absorpt_correction_T_min 0.776 _exptl_absorpt_correction_T_max 0.998 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 93 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_measurement_device_type 'Rigaku Mercury70' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 14.629 _diffrn_reflns_number 11384 _diffrn_reflns_av_R_equivalents 0.0534 _diffrn_reflns_theta_min 2.491 _diffrn_reflns_theta_max 25.329 _diffrn_reflns_theta_full 25.000 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_Laue_measured_fraction_max 0.996 _diffrn_reflns_Laue_measured_fraction_full 0.996 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 19 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 3286 _reflns_number_gt 2799 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0412 _refine_ls_wR_factor_ref 0.0989 _refine_ls_number_restraints 1 _refine_ls_hydrogen_treatment mixed _refine_ls_number_reflns 3286 _refine_ls_number_parameters 221 _refine_ls_goodness_of_fit_ref 0.896 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0573P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_diff_density_max 0.150 _refine_diff_density_min -0.190 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Parsons and Flack (2004), Acta Cryst. A60, s61' _refine_ls_abs_structure_Flack 0.1(7) 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 for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.0061 0.0033 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.0106 0.0060 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 O5 O 0.3890(3) 0.66622(13) 0.54219(10) 0.0370(5) Uani 1.0 4 d . . . O6 O 0.3758(3) 0.86204(12) 0.52232(10) 0.0369(5) Uani 1.0 4 d . . . O13 O 0.8961(3) 0.80580(13) 0.02915(9) 0.0378(5) Uani 1.0 4 d . . . N1 N 0.2587(3) 0.75253(13) 0.43779(11) 0.0245(5) Uani 1.0 4 d . . . N2 N 0.1614(3) 0.73303(14) 0.36494(11) 0.0265(5) Uani 1.0 4 d . . . C3 C 0.2222(4) 0.63703(16) 0.34051(14) 0.0305(6) Uani 1.0 4 d . . . C4 C 0.2615(4) 0.58988(16) 0.42261(14) 0.0308(6) Uani 1.0 4 d . . . C5 C 0.3127(4) 0.67004(17) 0.47730(14) 0.0282(6) Uani 1.0 4 d . . . C6 C 0.3030(4) 0.84479(16) 0.45803(13) 0.0262(6) Uani 1.0 4 d . . . C7 C 0.2576(4) 0.91879(15) 0.39512(13) 0.0271(6) Uani 1.0 4 d . . . C8 C 0.3611(4) 0.90429(15) 0.31744(14) 0.0243(6) Uani 1.0 4 d . . . C9 C 0.5323(4) 0.87863(16) 0.31819(14) 0.0257(6) Uani 1.0 4 d . . . C10 C 0.6241(4) 0.86105(15) 0.24449(14) 0.0247(6) Uani 1.0 4 d . . . C11 C 0.7987(4) 0.82991(16) 0.24423(14) 0.0295(6) Uani 1.0 4 d . . . C12 C 0.8820(4) 0.81163(17) 0.17213(14) 0.0310(6) Uani 1.0 4 d . . . C13 C 0.7966(4) 0.82401(17) 0.09685(14) 0.0294(6) Uani 1.0 4 d . . . C14 C 0.6279(4) 0.85200(17) 0.09439(15) 0.0290(6) Uani 1.0 4 d . . . C15 C 0.5376(4) 0.87146(16) 0.16843(14) 0.0251(6) Uani 1.0 4 d . . . C16 C 0.3629(4) 0.90074(17) 0.16911(14) 0.0288(6) Uani 1.0 4 d . . . C17 C 0.2784(4) 0.91608(15) 0.24101(14) 0.0273(6) Uani 1.0 4 d . . . C18 C 0.0793(4) 0.58987(18) 0.29229(16) 0.0395(8) Uani 1.0 4 d . . . C19 C 0.3867(4) 0.64702(18) 0.28985(15) 0.0368(7) Uani 1.0 4 d . . . C20 C 0.2821(5) 1.01753(17) 0.43054(16) 0.0402(7) Uani 1.0 4 d . . . C21 C 0.8178(4) 0.8220(2) -0.04888(14) 0.0413(7) Uani 1.0 4 d . . . H2 H 0.0453(16) 0.730(2) 0.3883(14) 0.039(8) Uiso 1.0 4 d . . . H4A H 0.1581 0.5572 0.4442 0.0370 Uiso 1.0 4 calc R . . H4B H 0.3569 0.5440 0.4171 0.0370 Uiso 1.0 4 calc R . . H7 H 0.1326 0.9112 0.3811 0.0325 Uiso 1.0 4 calc R . . H9 H 0.5905 0.8725 0.3691 0.0309 Uiso 1.0 4 calc R . . H11 H 0.8581 0.8217 0.2946 0.0355 Uiso 1.0 4 calc R . . H12 H 0.9984 0.7904 0.1729 0.0372 Uiso 1.0 4 calc R . . H14 H 0.5707 0.8585 0.0433 0.0348 Uiso 1.0 4 calc R . . H16 H 0.3038 0.9098 0.1188 0.0345 Uiso 1.0 4 calc R . . H17 H 0.1608 0.9352 0.2397 0.0327 Uiso 1.0 4 calc R . . H18A H 0.0523 0.6276 0.2438 0.0474 Uiso 1.0 4 calc R . . H18B H -0.0241 0.5843 0.3266 0.0474 Uiso 1.0 4 calc R . . H18C H 0.1173 0.5272 0.2753 0.0474 Uiso 1.0 4 calc R . . H19A H 0.3665 0.6913 0.2450 0.0442 Uiso 1.0 4 calc R . . H19B H 0.4189 0.5857 0.2673 0.0442 Uiso 1.0 4 calc R . . H19C H 0.4804 0.6704 0.3246 0.0442 Uiso 1.0 4 calc R . . H20A H 0.4031 1.0260 0.4468 0.0483 Uiso 1.0 4 calc R . . H20B H 0.2073 1.0254 0.4784 0.0483 Uiso 1.0 4 calc R . . H20C H 0.2516 1.0644 0.3891 0.0483 Uiso 1.0 4 calc R . . H21A H 0.7850 0.8882 -0.0535 0.0496 Uiso 1.0 4 calc R . . H21B H 0.7146 0.7826 -0.0543 0.0496 Uiso 1.0 4 calc R . . H21C H 0.9002 0.8062 -0.0923 0.0496 Uiso 1.0 4 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O5 0.0348(11) 0.0417(11) 0.0346(10) 0.0016(10) -0.0061(9) 0.0091(9) O6 0.0427(12) 0.0382(10) 0.0296(9) -0.0031(10) -0.0073(10) -0.0031(8) O13 0.0344(11) 0.0498(11) 0.0292(9) 0.0035(10) 0.0058(9) -0.0056(9) N1 0.0262(12) 0.0263(10) 0.0210(9) -0.0004(10) -0.0035(10) 0.0014(9) N2 0.0281(13) 0.0274(11) 0.0239(10) 0.0006(10) -0.0037(10) -0.0019(9) C3 0.0336(16) 0.0245(12) 0.0334(13) -0.0007(12) 0.0012(12) -0.0014(11) C4 0.0303(15) 0.0243(12) 0.0378(14) 0.0013(12) 0.0038(13) 0.0021(12) C5 0.0233(14) 0.0313(13) 0.0302(12) 0.0031(12) 0.0059(11) 0.0055(12) C6 0.0232(14) 0.0282(13) 0.0271(12) -0.0001(11) 0.0031(11) -0.0024(11) C7 0.0270(15) 0.0261(12) 0.0281(12) 0.0005(11) 0.0013(12) -0.0009(11) C8 0.0258(15) 0.0200(12) 0.0270(12) -0.0029(11) -0.0015(11) 0.0005(11) C9 0.0280(15) 0.0244(13) 0.0248(12) -0.0029(11) -0.0023(11) 0.0023(10) C10 0.0229(13) 0.0215(11) 0.0296(13) -0.0013(11) -0.0022(11) 0.0016(11) C11 0.0265(14) 0.0320(13) 0.0301(12) 0.0008(12) -0.0017(11) 0.0018(12) C12 0.0239(14) 0.0340(14) 0.0352(13) 0.0005(13) 0.0000(12) -0.0011(12) C13 0.0332(16) 0.0273(13) 0.0277(12) -0.0028(12) 0.0050(11) -0.0012(11) C14 0.0302(15) 0.0295(13) 0.0273(12) -0.0016(12) -0.0027(11) 0.0000(11) C15 0.0263(14) 0.0236(12) 0.0254(12) -0.0032(11) -0.0014(11) 0.0030(10) C16 0.0280(15) 0.0323(13) 0.0260(12) 0.0008(12) -0.0045(11) 0.0041(11) C17 0.0236(14) 0.0273(12) 0.0310(13) 0.0014(11) 0.0001(12) 0.0030(11) C18 0.047(2) 0.0293(14) 0.0419(16) -0.0047(14) -0.0037(15) -0.0060(12) C19 0.0417(17) 0.0306(14) 0.0382(14) 0.0002(14) 0.0089(13) -0.0028(12) C20 0.0523(19) 0.0290(13) 0.0394(14) -0.0004(14) 0.0047(15) -0.0038(12) C21 0.0439(18) 0.0490(16) 0.0311(13) 0.0015(15) 0.0043(13) -0.0052(13) #============================================================================== _computing_data_collection 'CrystalClear-SM Expert 2.0 rc13 (Rigaku, 2009)' _computing_cell_refinement 'CrystalClear-SM Expert 2.0 rc13' _computing_data_reduction 'CrystalClear-SM Expert 2.0 rc13' _computing_structure_solution 'SIR2004 (Burla, et al., 2005)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 O5 C5 1.215(3) yes . . O6 C6 1.218(3) yes . . O13 C13 1.373(3) yes . . O13 C21 1.431(3) yes . . N1 N2 1.436(3) yes . . N1 C5 1.404(3) yes . . N1 C6 1.398(3) yes . . N2 C3 1.500(3) yes . . C3 C4 1.532(4) yes . . C3 C18 1.515(4) yes . . C3 C19 1.525(4) yes . . C4 C5 1.503(4) yes . . C6 C7 1.514(4) yes . . C7 C8 1.515(4) yes . . C7 C20 1.533(4) yes . . C8 C9 1.373(4) yes . . C8 C17 1.414(4) yes . . C9 C10 1.421(4) yes . . C10 C11 1.422(4) yes . . C10 C15 1.420(4) yes . . C11 C12 1.369(4) yes . . C12 C13 1.408(4) yes . . C13 C14 1.365(4) yes . . C14 C15 1.425(4) yes . . C15 C16 1.414(4) yes . . C16 C17 1.363(4) yes . . N2 H2 0.977(15) no . . C4 H4A 0.990 no . . C4 H4B 0.990 no . . C7 H7 1.000 no . . C9 H9 0.950 no . . C11 H11 0.950 no . . C12 H12 0.950 no . . C14 H14 0.950 no . . C16 H16 0.950 no . . C17 H17 0.950 no . . C18 H18A 0.980 no . . C18 H18B 0.980 no . . C18 H18C 0.980 no . . C19 H19A 0.980 no . . C19 H19B 0.980 no . . C19 H19C 0.980 no . . C20 H20A 0.980 no . . C20 H20B 0.980 no . . C20 H20C 0.980 no . . C21 H21A 0.980 no . . C21 H21B 0.980 no . . C21 H21C 0.980 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C13 O13 C21 116.8(2) yes . . . N2 N1 C5 112.07(18) yes . . . N2 N1 C6 120.45(18) yes . . . C5 N1 C6 127.2(2) yes . . . N1 N2 C3 103.46(18) yes . . . N2 C3 C4 103.20(18) yes . . . N2 C3 C18 108.3(3) yes . . . N2 C3 C19 108.7(2) yes . . . C4 C3 C18 114.0(2) yes . . . C4 C3 C19 110.6(3) yes . . . C18 C3 C19 111.5(2) yes . . . C3 C4 C5 103.94(19) yes . . . O5 C5 N1 125.7(3) yes . . . O5 C5 C4 127.8(3) yes . . . N1 C5 C4 106.45(19) yes . . . O6 C6 N1 120.5(2) yes . . . O6 C6 C7 123.6(2) yes . . . N1 C6 C7 115.89(19) yes . . . C6 C7 C8 110.6(2) yes . . . C6 C7 C20 110.69(19) yes . . . C8 C7 C20 112.1(2) yes . . . C7 C8 C9 122.5(3) yes . . . C7 C8 C17 119.1(3) yes . . . C9 C8 C17 118.4(3) yes . . . C8 C9 C10 121.4(3) yes . . . C9 C10 C11 122.2(3) yes . . . C9 C10 C15 119.3(3) yes . . . C11 C10 C15 118.5(2) yes . . . C10 C11 C12 120.6(3) yes . . . C11 C12 C13 120.6(3) yes . . . O13 C13 C12 114.7(3) yes . . . O13 C13 C14 124.6(3) yes . . . C12 C13 C14 120.7(3) yes . . . C13 C14 C15 120.0(3) yes . . . C10 C15 C14 119.6(3) yes . . . C10 C15 C16 118.3(3) yes . . . C14 C15 C16 122.2(3) yes . . . C15 C16 C17 120.8(3) yes . . . C8 C17 C16 121.8(3) yes . . . N1 N2 H2 99.5(13) no . . . C3 N2 H2 110.9(17) no . . . C3 C4 H4A 110.971 no . . . C3 C4 H4B 110.967 no . . . C5 C4 H4A 110.970 no . . . C5 C4 H4B 110.972 no . . . H4A C4 H4B 108.976 no . . . C6 C7 H7 107.737 no . . . C8 C7 H7 107.744 no . . . C20 C7 H7 107.732 no . . . C8 C9 H9 119.298 no . . . C10 C9 H9 119.299 no . . . C10 C11 H11 119.693 no . . . C12 C11 H11 119.691 no . . . C11 C12 H12 119.720 no . . . C13 C12 H12 119.730 no . . . C13 C14 H14 119.992 no . . . C15 C14 H14 119.991 no . . . C15 C16 H16 119.584 no . . . C17 C16 H16 119.594 no . . . C8 C17 H17 119.119 no . . . C16 C17 H17 119.111 no . . . C3 C18 H18A 109.467 no . . . C3 C18 H18B 109.472 no . . . C3 C18 H18C 109.475 no . . . H18A C18 H18B 109.469 no . . . H18A C18 H18C 109.469 no . . . H18B C18 H18C 109.476 no . . . C3 C19 H19A 109.470 no . . . C3 C19 H19B 109.473 no . . . C3 C19 H19C 109.473 no . . . H19A C19 H19B 109.460 no . . . H19A C19 H19C 109.476 no . . . H19B C19 H19C 109.476 no . . . C7 C20 H20A 109.469 no . . . C7 C20 H20B 109.479 no . . . C7 C20 H20C 109.472 no . . . H20A C20 H20B 109.473 no . . . H20A C20 H20C 109.466 no . . . H20B C20 H20C 109.468 no . . . O13 C21 H21A 109.465 no . . . O13 C21 H21B 109.474 no . . . O13 C21 H21C 109.471 no . . . H21A C21 H21B 109.464 no . . . H21A C21 H21C 109.471 no . . . H21B C21 H21C 109.483 no . . . 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C21 O13 C13 C12 -176.9(2) no . . . . C21 O13 C13 C14 3.1(4) no . . . . N2 N1 C5 O5 -175.9(2) no . . . . N2 N1 C5 C4 5.4(3) no . . . . C5 N1 N2 C3 -24.4(3) no . . . . N2 N1 C6 O6 175.27(19) no . . . . N2 N1 C6 C7 -5.7(3) no . . . . C6 N1 N2 C3 149.86(19) no . . . . C5 N1 C6 O6 -11.4(4) no . . . . C5 N1 C6 C7 167.6(2) no . . . . C6 N1 C5 O5 10.3(4) no . . . . C6 N1 C5 C4 -168.3(2) no . . . . N1 N2 C3 C4 32.4(2) no . . . . N1 N2 C3 C18 153.58(16) no . . . . N1 N2 C3 C19 -85.04(19) no . . . . N2 C3 C4 C5 -29.5(3) no . . . . C18 C3 C4 C5 -146.7(2) no . . . . C19 C3 C4 C5 86.7(3) no . . . . C3 C4 C5 O5 -163.1(3) no . . . . C3 C4 C5 N1 15.4(3) no . . . . O6 C6 C7 C8 113.6(3) no . . . . O6 C6 C7 C20 -11.3(4) no . . . . N1 C6 C7 C8 -65.4(3) no . . . . N1 C6 C7 C20 169.71(19) no . . . . C6 C7 C8 C9 -40.0(3) no . . . . C6 C7 C8 C17 138.96(19) no . . . . C20 C7 C8 C9 84.1(3) no . . . . C20 C7 C8 C17 -96.9(3) no . . . . C7 C8 C9 C10 176.90(18) no . . . . C7 C8 C17 C16 -177.61(18) no . . . . C9 C8 C17 C16 1.4(4) no . . . . C17 C8 C9 C10 -2.1(4) no . . . . C8 C9 C10 C11 -176.80(19) no . . . . C8 C9 C10 C15 0.9(4) no . . . . C9 C10 C11 C12 178.52(19) no . . . . C9 C10 C15 C14 -178.67(18) no . . . . C9 C10 C15 C16 1.1(3) no . . . . C11 C10 C15 C14 -0.9(3) no . . . . C11 C10 C15 C16 178.82(18) no . . . . C15 C10 C11 C12 0.9(4) no . . . . C10 C11 C12 C13 0.5(4) no . . . . C11 C12 C13 O13 178.2(2) no . . . . C11 C12 C13 C14 -1.8(4) no . . . . O13 C13 C14 C15 -178.3(2) no . . . . C12 C13 C14 C15 1.7(4) no . . . . C13 C14 C15 C10 -0.3(4) no . . . . C13 C14 C15 C16 179.9(2) no . . . . C10 C15 C16 C17 -1.8(4) no . . . . C14 C15 C16 C17 178.0(2) no . . . . C15 C16 C17 C8 0.5(4) no . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 O5 O6 2.810(3) no . . O5 N2 3.522(3) no . . O5 C3 3.566(3) no . . O5 C6 2.967(3) no . . O6 N2 3.571(3) no . . O6 C5 2.874(3) no . . O6 C8 3.406(3) no . . O6 C9 3.558(3) no . . O6 C20 2.772(3) no . . N1 C8 3.029(3) no . . N1 C9 3.395(4) no . . N1 C18 3.599(4) no . . N1 C19 3.015(4) no . . N2 C7 2.792(3) no . . N2 C8 2.990(3) no . . N2 C17 3.424(3) no . . C3 C6 3.583(4) no . . C5 C19 3.135(4) no . . C6 C9 2.933(4) no . . C8 C15 2.832(4) no . . C9 C16 2.785(4) no . . C9 C19 3.516(4) no . . C9 C20 3.321(4) no . . C10 C13 2.809(4) no . . C10 C17 2.787(4) no . . C11 C14 2.801(4) no . . C12 C15 2.797(4) no . . C14 C21 2.798(4) no . . C17 C20 3.420(4) no . . O5 N1 3.102(3) no . 2_566 O5 N2 2.967(3) no . 2_566 O5 C6 3.206(4) no . 2_566 O5 C7 3.263(4) no . 2_566 O5 C11 3.562(3) no . 2_466 O6 N1 3.444(3) no . 2_566 O6 N2 3.180(3) no . 2_566 O6 C3 3.494(4) no . 2_566 O6 C4 3.190(4) no . 2_566 O6 C5 3.410(4) no . 2_566 O6 C18 3.484(4) no . 2_566 O13 C14 3.514(3) no . 2_565 N1 O5 3.102(3) no . 2_466 N1 O6 3.444(3) no . 2_466 N2 O5 2.967(3) no . 2_466 N2 O6 3.180(3) no . 2_466 C3 O6 3.494(4) no . 2_466 C4 O6 3.190(4) no . 2_466 C4 C14 3.505(4) no . 3_645 C5 O6 3.410(4) no . 2_466 C6 O5 3.206(4) no . 2_466 C7 O5 3.263(4) no . 2_466 C11 O5 3.562(3) no . 2_566 C12 C17 3.589(4) no . 1_655 C14 O13 3.514(3) no . 2_465 C14 C4 3.505(4) no . 3_655 C14 C21 3.528(4) no . 2_465 C17 C12 3.589(4) no . 1_455 C18 O6 3.484(4) no . 2_466 C21 C14 3.528(4) no . 2_565 O5 H4A 2.8582 no . . O5 H4B 2.6967 no . . O6 H7 3.0595 no . . O6 H9 3.0100 no . . O6 H20A 2.6503 no . . O6 H20B 2.7613 no . . O13 H12 2.4898 no . . O13 H14 2.6367 no . . N1 H4A 2.8903 no . . N1 H4B 3.0837 no . . N1 H7 2.6303 no . . N1 H9 3.2814 no . . N1 H19A 3.3753 no . . N1 H19C 2.7803 no . . N2 H4A 2.8192 no . . N2 H4B 3.2035 no . . N2 H7 2.5615 no . . N2 H17 3.5333 no . . N2 H18A 2.6246 no . . N2 H18B 2.6338 no . . N2 H18C 3.2955 no . . N2 H19A 2.5915 no . . N2 H19B 3.3046 no . . N2 H19C 2.7051 no . . C4 H2 2.67(3) no . . C4 H18A 3.3842 no . . C4 H18B 2.7110 no . . C4 H18C 2.8012 no . . C4 H19A 3.3440 no . . C4 H19B 2.8171 no . . C4 H19C 2.5981 no . . C5 H2 2.671(19) no . . C5 H19C 2.8131 no . . C6 H2 2.82(2) no . . C6 H9 2.6862 no . . C6 H19C 3.5784 no . . C6 H20A 2.7007 no . . C6 H20B 2.6969 no . . C6 H20C 3.3481 no . . C7 H2 3.15(3) no . . C7 H9 2.6915 no . . C7 H17 2.6594 no . . C8 H16 3.2791 no . . C8 H19A 3.2563 no . . C8 H19C 3.4579 no . . C8 H20A 2.7538 no . . C8 H20B 3.3643 no . . C8 H20C 2.6995 no . . C9 H7 3.2914 no . . C9 H11 2.6756 no . . C9 H17 3.2482 no . . C9 H19A 3.1925 no . . C9 H19C 2.9939 no . . C9 H20A 3.1345 no . . C10 H12 3.2815 no . . C10 H14 3.3161 no . . C10 H16 3.2931 no . . C10 H19A 3.1326 no . . C10 H19C 3.2130 no . . C11 H9 2.6699 no . . C11 H19C 3.5985 no . . C12 H14 3.2685 no . . C13 H11 3.2683 no . . C13 H21A 2.6247 no . . C13 H21B 2.6193 no . . C13 H21C 3.2047 no . . C14 H12 3.2605 no . . C14 H16 2.6692 no . . C14 H21A 2.7550 no . . C14 H21B 2.7091 no . . C15 H9 3.3063 no . . C15 H11 3.3018 no . . C15 H17 3.2681 no . . C15 H19A 3.1468 no . . C16 H14 2.6789 no . . C16 H19A 3.2305 no . . C17 H7 2.5553 no . . C17 H9 3.2553 no . . C17 H19A 3.2732 no . . C17 H20C 3.2196 no . . C18 H2 2.56(3) no . . C18 H4A 2.5991 no . . C18 H4B 3.0340 no . . C18 H19A 2.7601 no . . C18 H19B 2.6590 no . . C18 H19C 3.3496 no . . C19 H2 3.313(18) no . . C19 H4A 3.3364 no . . C19 H4B 2.5567 no . . C19 H18A 2.7076 no . . C19 H18B 3.3545 no . . C19 H18C 2.7041 no . . C20 H9 3.3117 no . . C20 H17 3.4627 no . . C21 H14 2.4892 no . . H2 H4A 2.7700 no . . H2 H7 2.6658 no . . H2 H18A 2.7802 no . . H2 H18B 2.3735 no . . H2 H18C 3.4785 no . . H2 H19A 3.4603 no . . H4A H18A 3.5224 no . . H4A H18B 2.4147 no . . H4A H18C 2.8128 no . . H4A H19B 3.5496 no . . H4A H19C 3.5547 no . . H4B H18B 3.3478 no . . H4B H18C 2.9794 no . . H4B H19A 3.5112 no . . H4B H19B 2.5659 no . . H4B H19C 2.5377 no . . H7 H9 3.5902 no . . H7 H17 2.3477 no . . H7 H20A 2.8639 no . . H7 H20B 2.3466 no . . H7 H20C 2.3710 no . . H9 H11 2.5083 no . . H9 H19C 3.0876 no . . H9 H20A 2.9149 no . . H11 H12 2.3102 no . . H14 H16 2.5143 no . . H14 H21A 2.3305 no . . H14 H21B 2.2262 no . . H14 H21C 3.4592 no . . H16 H17 2.2943 no . . H17 H20C 3.1369 no . . H18A H19A 2.5937 no . . H18A H19B 2.9230 no . . H18B H19B 3.5610 no . . H18C H19A 3.0699 no . . H18C H19B 2.4810 no . . H18C H19C 3.5641 no . . O5 H2 2.22(3) no . 2_566 O5 H7 2.5174 no . 2_566 O5 H9 2.7822 no . 2_466 O5 H11 2.6856 no . 2_466 O6 H2 2.36(3) no . 2_566 O6 H4A 2.5274 no . 2_566 O6 H18B 2.6998 no . 2_566 O13 H14 2.9503 no . 2_565 O13 H20A 3.1569 no . 4_674 O13 H21B 2.7965 no . 2_565 N2 H11 2.9019 no . 1_455 N2 H12 3.4813 no . 1_455 C4 H14 3.5852 no . 3_645 C4 H21A 3.6000 no . 3_645 C5 H2 3.17(3) no . 2_566 C5 H7 3.5801 no . 2_566 C5 H9 3.1039 no . 2_466 C6 H2 3.31(2) no . 2_566 C6 H4A 3.4706 no . 2_566 C8 H19B 3.3898 no . 3_655 C9 H19B 3.2856 no . 3_655 C10 H18C 3.1155 no . 3_655 C10 H19B 3.2225 no . 3_655 C11 H2 3.35(3) no . 1_655 C11 H17 3.1778 no . 1_655 C11 H18A 3.4858 no . 1_655 C11 H18C 2.9016 no . 3_655 C12 H17 2.9949 no . 1_655 C12 H18A 3.1590 no . 1_655 C12 H18C 3.1884 no . 3_655 C12 H21B 3.4825 no . 2_565 C13 H4A 3.4067 no . 3_655 C13 H4B 3.3588 no . 3_655 C13 H21C 3.5838 no . 2_465 C14 H4A 3.4178 no . 3_655 C14 H4B 2.7439 no . 3_655 C14 H21C 2.8600 no . 2_465 C15 H4B 2.9433 no . 3_655 C15 H18C 3.5907 no . 3_655 C15 H19B 3.2445 no . 3_655 C15 H21C 3.0139 no . 2_465 C16 H4B 3.2936 no . 3_655 C16 H12 3.2281 no . 1_455 C16 H19B 3.2965 no . 3_655 C16 H20B 3.3357 no . 4_574 C16 H21B 3.4142 no . 2_465 C16 H21C 3.2170 no . 2_465 C17 H12 3.0223 no . 1_455 C17 H18B 3.2912 no . 3_555 C17 H18C 3.4556 no . 3_555 C17 H19B 3.3667 no . 3_655 C18 H12 3.5158 no . 1_455 C18 H17 2.9282 no . 3_545 C19 H21C 3.3008 no . 2_465 C20 H16 3.3153 no . 4_575 C20 H21C 3.5325 no . 4_675 C21 H12 3.5740 no . 2_465 C21 H14 3.2314 no . 2_565 C21 H16 3.4952 no . 2_565 C21 H19A 3.2349 no . 2_565 C21 H20A 3.0586 no . 4_674 H2 O5 2.22(3) no . 2_466 H2 O6 2.36(3) no . 2_466 H2 C5 3.17(3) no . 2_466 H2 C6 3.31(2) no . 2_466 H2 C11 3.35(3) no . 1_455 H2 H11 2.4781 no . 1_455 H4A O6 2.5274 no . 2_466 H4A C6 3.4706 no . 2_466 H4A C13 3.4067 no . 3_645 H4A C14 3.4178 no . 3_645 H4A H9 3.2563 no . 2_466 H4A H14 3.5289 no . 3_645 H4A H20A 2.9113 no . 2_466 H4A H21A 3.0307 no . 3_645 H4B C13 3.3588 no . 3_645 H4B C14 2.7439 no . 3_645 H4B C15 2.9433 no . 3_645 H4B C16 3.2936 no . 3_645 H4B H14 2.7771 no . 3_645 H4B H16 3.2995 no . 3_645 H4B H20B 3.3522 no . 2_566 H4B H21A 3.3321 no . 3_645 H7 O5 2.5174 no . 2_466 H7 C5 3.5801 no . 2_466 H7 H11 2.8522 no . 1_455 H9 O5 2.7822 no . 2_566 H9 C5 3.1039 no . 2_566 H9 H4A 3.2563 no . 2_566 H11 O5 2.6856 no . 2_566 H11 N2 2.9019 no . 1_655 H11 H2 2.4781 no . 1_655 H11 H7 2.8522 no . 1_655 H11 H17 2.9828 no . 1_655 H11 H18A 3.2541 no . 1_655 H11 H18B 3.5407 no . 1_655 H11 H18C 3.1471 no . 3_655 H12 N2 3.4813 no . 1_655 H12 C16 3.2281 no . 1_655 H12 C17 3.0223 no . 1_655 H12 C18 3.5158 no . 1_655 H12 C21 3.5740 no . 2_565 H12 H16 3.0415 no . 1_655 H12 H17 2.6507 no . 1_655 H12 H18A 2.6259 no . 1_655 H12 H18C 3.5908 no . 3_655 H12 H19A 3.3889 no . 1_655 H12 H21B 2.7630 no . 2_565 H14 O13 2.9503 no . 2_465 H14 C4 3.5852 no . 3_655 H14 C21 3.2314 no . 2_465 H14 H4A 3.5289 no . 3_655 H14 H4B 2.7771 no . 3_655 H14 H20B 2.9127 no . 4_574 H14 H21B 3.4143 no . 2_465 H14 H21C 2.8077 no . 2_465 H16 C20 3.3153 no . 4_574 H16 C21 3.4952 no . 2_465 H16 H4B 3.2995 no . 3_655 H16 H12 3.0415 no . 1_455 H16 H18B 3.4135 no . 3_555 H16 H20A 3.3631 no . 4_574 H16 H20B 2.4761 no . 4_574 H16 H21B 3.0160 no . 2_465 H16 H21C 3.1954 no . 2_465 H17 C11 3.1778 no . 1_455 H17 C12 2.9949 no . 1_455 H17 C18 2.9282 no . 3_555 H17 H11 2.9828 no . 1_455 H17 H12 2.6507 no . 1_455 H17 H18A 3.2088 no . 3_555 H17 H18B 2.6082 no . 3_555 H17 H18C 2.5300 no . 3_555 H18A C11 3.4858 no . 1_455 H18A C12 3.1590 no . 1_455 H18A H11 3.2541 no . 1_455 H18A H12 2.6259 no . 1_455 H18A H17 3.2088 no . 3_545 H18A H20C 3.3258 no . 3_545 H18A H21B 3.5800 no . 2_465 H18B O6 2.6998 no . 2_466 H18B C17 3.2912 no . 3_545 H18B H11 3.5407 no . 1_455 H18B H16 3.4135 no . 3_545 H18B H17 2.6082 no . 3_545 H18C C10 3.1155 no . 3_645 H18C C11 2.9016 no . 3_645 H18C C12 3.1884 no . 3_645 H18C C15 3.5907 no . 3_645 H18C C17 3.4556 no . 3_545 H18C H11 3.1471 no . 3_645 H18C H12 3.5908 no . 3_645 H18C H17 2.5300 no . 3_545 H19A C21 3.2349 no . 2_465 H19A H12 3.3889 no . 1_455 H19A H21A 3.3895 no . 2_465 H19A H21B 3.3533 no . 2_465 H19A H21C 2.5118 no . 2_465 H19B C8 3.3898 no . 3_645 H19B C9 3.2856 no . 3_645 H19B C10 3.2225 no . 3_645 H19B C15 3.2445 no . 3_645 H19B C16 3.2965 no . 3_645 H19B C17 3.3667 no . 3_645 H19B H21C 3.2537 no . 2_465 H20A O13 3.1569 no . 4_675 H20A C21 3.0586 no . 4_675 H20A H4A 2.9113 no . 2_566 H20A H16 3.3631 no . 4_575 H20A H21A 2.7046 no . 4_675 H20A H21C 2.9039 no . 4_675 H20B C16 3.3357 no . 4_575 H20B H4B 3.3522 no . 2_466 H20B H14 2.9127 no . 4_575 H20B H16 2.4761 no . 4_575 H20C H18A 3.3258 no . 3_555 H20C H21C 3.2776 no . 4_675 H21A C4 3.6000 no . 3_655 H21A H4A 3.0307 no . 3_655 H21A H4B 3.3321 no . 3_655 H21A H19A 3.3895 no . 2_565 H21A H20A 2.7046 no . 4_674 H21B O13 2.7965 no . 2_465 H21B C12 3.4825 no . 2_465 H21B C16 3.4142 no . 2_565 H21B H12 2.7630 no . 2_465 H21B H14 3.4143 no . 2_565 H21B H16 3.0160 no . 2_565 H21B H18A 3.5800 no . 2_565 H21B H19A 3.3533 no . 2_565 H21C C13 3.5838 no . 2_565 H21C C14 2.8600 no . 2_565 H21C C15 3.0139 no . 2_565 H21C C16 3.2170 no . 2_565 H21C C19 3.3008 no . 2_565 H21C C20 3.5325 no . 4_674 H21C H14 2.8077 no . 2_565 H21C H16 3.1954 no . 2_565 H21C H19A 2.5118 no . 2_565 H21C H19B 3.2537 no . 2_565 H21C H20A 2.9039 no . 4_674 H21C H20C 3.2776 no . 4_674 #============================================================================== loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_distance_DA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_angle_DHA _geom_hbond_publ_flag N2 H2 O5 . . 2_466 2.967(3) 0.977 2.219(15) 132(2) no #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #============================================================================== _database_code_depnum_ccdc_archive 'CCDC 956171' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_16 #TrackingRef '17923_web_deposit_cif_file_0_EoinGould_1361367350.16.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H27 F3 N2 O7 S' _chemical_formula_sum 'C28 H27 F3 N2 O7 S' _chemical_formula_weight 592.58 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' S S 0.1246 0.1234 '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 13.223(4) _cell_length_b 13.332(3) _cell_length_c 17.956(4) _cell_angle_alpha 91.021(6) _cell_angle_beta 91.959(4) _cell_angle_gamma 114.349(8) _cell_volume 2880.3(12) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 8435 _cell_measurement_theta_min 1.7 _cell_measurement_theta_max 28.5 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.367 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1232 _exptl_absorpt_coefficient_mu 0.179 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.821 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type CCD _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17984 _diffrn_reflns_av_R_equivalents 0.0312 _diffrn_reflns_av_sigmaI/netI 0.0785 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 25.34 _reflns_number_total 10048 _reflns_number_gt 6916 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _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. The NH hydrogen atoms were located from a difference map and refined isotropically subject to a distance restraint. ; _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^)+(0.0994P)^2^+0.8272P] 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 10048 _refine_ls_number_parameters 747 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0942 _refine_ls_R_factor_gt 0.0635 _refine_ls_wR_factor_ref 0.2151 _refine_ls_wR_factor_gt 0.1683 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _refine_ls_shift/su_max 0.050 _refine_ls_shift/su_mean 0.002 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.4133(2) 1.0439(2) 1.31231(16) 0.0345(7) Uani 1 1 d . . . N2 N 0.3977(3) 0.9365(2) 1.32470(17) 0.0357(7) Uani 1 1 d D . . H2N H 0.457(2) 0.934(3) 1.3553(18) 0.047(11) Uiso 1 1 d D . . O3 O 0.2583(2) 0.8690(2) 1.23294(15) 0.0464(7) Uani 1 1 d . . . C3 C 0.3184(3) 0.8540(3) 1.2790(2) 0.0371(9) Uani 1 1 d . . . O4 O 0.3235(2) 0.75932(19) 1.29539(15) 0.0441(7) Uani 1 1 d . . . C5 C 0.2349(3) 0.6601(3) 1.2592(2) 0.0498(10) Uani 1 1 d . . . H5A H 0.2647 0.6048 1.2477 0.060 Uiso 1 1 calc R . . H5B H 0.2085 0.6798 1.2117 0.060 Uiso 1 1 calc R . . C6 C 0.1398(3) 0.6120(3) 1.3099(2) 0.0457(10) Uani 1 1 d . . . C7 C 0.0741(3) 0.6676(3) 1.3257(2) 0.0488(10) Uani 1 1 d . . . H7A H 0.0895 0.7365 1.3037 0.059 Uiso 1 1 calc R . . C8 C -0.0135(4) 0.6251(4) 1.3726(3) 0.0634(12) Uani 1 1 d . . . H8A H -0.0580 0.6640 1.3823 0.076 Uiso 1 1 calc R . . C9 C -0.0352(5) 0.5279(5) 1.4045(3) 0.0819(16) Uani 1 1 d . . . H9A H -0.0947 0.4987 1.4373 0.098 Uiso 1 1 calc R . . C10 C 0.0290(5) 0.4702(4) 1.3897(3) 0.0839(17) Uani 1 1 d . . . H10A H 0.0132 0.4014 1.4118 0.101 Uiso 1 1 calc R . . C11 C 0.1160(4) 0.5137(4) 1.3428(3) 0.0618(12) Uani 1 1 d . . . H11A H 0.1603 0.4745 1.3331 0.074 Uiso 1 1 calc R . . C12 C 0.3803(3) 1.1006(3) 1.37220(19) 0.0316(8) Uani 1 1 d . . . H12A H 0.3977 1.1770 1.3557 0.038 Uiso 1 1 calc R . . C13 C 0.4519(3) 1.1112(3) 1.44178(19) 0.0346(8) Uani 1 1 d . . . H13A H 0.4228 1.1394 1.4835 0.042 Uiso 1 1 calc R . . H13B H 0.4462 1.0372 1.4546 0.042 Uiso 1 1 calc R . . O14 O 0.6086(2) 1.2449(2) 1.38251(14) 0.0457(7) Uani 1 1 d . . . C14 C 0.5722(3) 1.1863(3) 1.4341(2) 0.0347(8) Uani 1 1 d . . . O15 O 0.6336(2) 1.18405(19) 1.49428(14) 0.0405(6) Uani 1 1 d . . . C16 C 0.7510(3) 1.2573(3) 1.4938(2) 0.0494(10) Uani 1 1 d . . . H16A H 0.7889 1.2493 1.5397 0.074 Uiso 1 1 calc R . . H16B H 0.7594 1.3336 1.4907 0.074 Uiso 1 1 calc R . . H16C H 0.7838 1.2383 1.4506 0.074 Uiso 1 1 calc R . . C17 C 0.2564(3) 1.0459(3) 1.38210(19) 0.0327(8) Uani 1 1 d . . . C18 C 0.2105(3) 0.9819(3) 1.4418(2) 0.0396(9) Uani 1 1 d . . . H18A H 0.2569 0.9680 1.4780 0.047 Uiso 1 1 calc R . . C19 C 0.0963(3) 0.9376(3) 1.4489(2) 0.0481(10) Uani 1 1 d . . . H19A H 0.0649 0.8930 1.4900 0.058 Uiso 1 1 calc R . . C20 C 0.0281(3) 0.9573(3) 1.3976(2) 0.0489(10) Uani 1 1 d . . . H20A H -0.0499 0.9273 1.4029 0.059 Uiso 1 1 calc R . . C21 C 0.0751(4) 1.0218(3) 1.3379(2) 0.0522(11) Uani 1 1 d . . . H21A H 0.0289 1.0367 1.3021 0.063 Uiso 1 1 calc R . . C22 C 0.1881(3) 1.0645(3) 1.3298(2) 0.0459(10) Uani 1 1 d . . . H22A H 0.2191 1.1071 1.2878 0.055 Uiso 1 1 calc R . . C23 C 0.4580(3) 1.0941(3) 1.25129(19) 0.0348(8) Uani 1 1 d . . . H23A H 0.4598 1.1652 1.2439 0.042 Uiso 1 1 calc R . . C24 C 0.5031(3) 1.0500(3) 1.19633(19) 0.0334(8) Uani 1 1 d . . . H24A H 0.5059 0.9805 1.2020 0.040 Uiso 1 1 calc R . . C25 C 0.5421(3) 1.1092(3) 1.1354(2) 0.0409(9) Uani 1 1 d . . . H25A H 0.5304 1.1745 1.1309 0.049 Uiso 1 1 calc R . . C26 C 0.6003(3) 1.0831(3) 1.07615(19) 0.0362(9) Uani 1 1 d . . . C27 C 0.6179(3) 1.1437(3) 1.0111(2) 0.0444(10) Uani 1 1 d . . . H27A H 0.5900 1.1987 1.0062 0.053 Uiso 1 1 calc R . . C28 C 0.6759(4) 1.1238(3) 0.9536(2) 0.0530(11) Uani 1 1 d . . . H28A H 0.6872 1.1646 0.9095 0.064 Uiso 1 1 calc R . . C29 C 0.7167(4) 1.0449(3) 0.9610(2) 0.0528(11) Uani 1 1 d . . . H29A H 0.7549 1.0302 0.9213 0.063 Uiso 1 1 calc R . . C30 C 0.7027(4) 0.9865(3) 1.0255(3) 0.0576(12) Uani 1 1 d . . . H30A H 0.7330 0.9334 1.0305 0.069 Uiso 1 1 calc R . . C31 C 0.6453(4) 1.0052(3) 1.0822(2) 0.0475(10) Uani 1 1 d . . . H31A H 0.6359 0.9645 1.1263 0.057 Uiso 1 1 calc R . . S32 S 0.66632(8) 0.92323(7) 1.33824(5) 0.0348(2) Uani 1 1 d . . . O34 O 0.6050(2) 0.9600(2) 1.38903(13) 0.0411(6) Uani 1 1 d . . . O35 O 0.6079(2) 0.88141(19) 1.26700(13) 0.0407(6) Uani 1 1 d . . . O36 O 0.7207(2) 0.8599(2) 1.37044(15) 0.0523(7) Uani 1 1 d . . . C33 C 0.7796(3) 1.0524(3) 1.3146(2) 0.0395(9) Uani 1 1 d . . . F37 F 0.73968(19) 1.12275(17) 1.29037(13) 0.0543(6) Uani 1 1 d . . . F38 F 0.84773(19) 1.09993(18) 1.37335(13) 0.0539(6) Uani 1 1 d . . . F39 F 0.83922(19) 1.03599(19) 1.26141(13) 0.0554(6) Uani 1 1 d . . . N41 N 0.5857(2) 0.6150(2) 1.19093(15) 0.0335(7) Uani 1 1 d . . . N42 N 0.6003(3) 0.5194(2) 1.17554(17) 0.0401(8) Uani 1 1 d D . . H42N H 0.537(2) 0.469(2) 1.1493(18) 0.037(11) Uiso 1 1 d D . . O43 O 0.7276(3) 0.5590(2) 1.27490(16) 0.0529(8) Uani 1 1 d . . . C43 C 0.6729(4) 0.4977(3) 1.2264(2) 0.0424(10) Uani 1 1 d . . . O44 O 0.6615(3) 0.3955(2) 1.20805(16) 0.0537(8) Uani 1 1 d . . . C45 C 0.7506(4) 0.3701(4) 1.2436(2) 0.0553(11) Uani 1 1 d . . . H45A H 0.7197 0.2927 1.2592 0.066 Uiso 1 1 calc R . . H45B H 0.7831 0.4187 1.2885 0.066 Uiso 1 1 calc R . . C46 C 0.8389(3) 0.3881(3) 1.1880(2) 0.0464(10) Uani 1 1 d . . . C47 C 0.9122(4) 0.4956(4) 1.1708(2) 0.0516(11) Uani 1 1 d . . . H47A H 0.9094 0.5574 1.1962 0.062 Uiso 1 1 calc R . . C48 C 0.9881(4) 0.5104(4) 1.1168(3) 0.0539(11) Uani 1 1 d . . . H48A H 1.0393 0.5823 1.1051 0.065 Uiso 1 1 calc R . . C49 C 0.9883(4) 0.4180(4) 1.0797(3) 0.0564(12) Uani 1 1 d . . . H49A H 1.0387 0.4276 1.0412 0.068 Uiso 1 1 calc R . . C50 C 0.9180(4) 0.3141(4) 1.0972(2) 0.0589(12) Uani 1 1 d . . . H50A H 0.9209 0.2523 1.0718 0.071 Uiso 1 1 calc R . . C51 C 0.8441(4) 0.2992(3) 1.1508(2) 0.0515(11) Uani 1 1 d . . . H51A H 0.7952 0.2266 1.1628 0.062 Uiso 1 1 calc R . . C52 C 0.6320(3) 0.7042(3) 1.13616(19) 0.0334(8) Uani 1 1 d . . . H52A H 0.6184 0.7688 1.1542 0.040 Uiso 1 1 calc R . . C53 C 0.5675(3) 0.6624(3) 1.06227(19) 0.0358(8) Uani 1 1 d . . . H53A H 0.6001 0.7186 1.0244 0.043 Uiso 1 1 calc R . . H53B H 0.5752 0.5948 1.0456 0.043 Uiso 1 1 calc R . . O54 O 0.4048(2) 0.6640(2) 1.11802(15) 0.0491(7) Uani 1 1 d . . . C54 C 0.4461(3) 0.6373(3) 1.0666(2) 0.0376(9) Uani 1 1 d . . . O55 O 0.3889(2) 0.5826(2) 1.00439(14) 0.0438(6) Uani 1 1 d . . . C56 C 0.2703(3) 0.5505(4) 1.0035(3) 0.0545(11) Uani 1 1 d . . . H56A H 0.2363 0.5113 0.9562 0.082 Uiso 1 1 calc R . . H56B H 0.2553 0.6163 1.0087 0.082 Uiso 1 1 calc R . . H56C H 0.2388 0.5021 1.0449 0.082 Uiso 1 1 calc R . . C57 C 0.7565(3) 0.7400(3) 1.1340(2) 0.0367(9) Uani 1 1 d . . . C58 C 0.8080(4) 0.7352(3) 1.0685(2) 0.0505(10) Uani 1 1 d . . . H58A H 0.7649 0.7080 1.0233 0.061 Uiso 1 1 calc R . . C59 C 0.9236(4) 0.7707(4) 1.0695(3) 0.0590(12) Uani 1 1 d . . . H59A H 0.9587 0.7688 1.0246 0.071 Uiso 1 1 calc R . . C60 C 0.9863(4) 0.8080(3) 1.1343(3) 0.0591(12) Uani 1 1 d . . . H60A H 1.0645 0.8307 1.1348 0.071 Uiso 1 1 calc R . . C61 C 0.9348(4) 0.8125(3) 1.1992(3) 0.0532(11) Uani 1 1 d . . . H61A H 0.9783 0.8387 1.2444 0.064 Uiso 1 1 calc R . . C62 C 0.8211(3) 0.7796(3) 1.1995(2) 0.0428(9) Uani 1 1 d . . . H62A H 0.7872 0.7841 1.2444 0.051 Uiso 1 1 calc R . . C63 C 0.5344(3) 0.6246(3) 1.2489(2) 0.0368(8) Uani 1 1 d . . . H63A H 0.5319 0.6940 1.2580 0.044 Uiso 1 1 calc R . . C64 C 0.4817(3) 0.5413(3) 1.30000(19) 0.0357(8) Uani 1 1 d . . . H64A H 0.4735 0.4679 1.2907 0.043 Uiso 1 1 calc R . . C65 C 0.4434(3) 0.5689(3) 1.3623(2) 0.0371(9) Uani 1 1 d . . . H65A H 0.4543 0.6437 1.3682 0.045 Uiso 1 1 calc R . . C66 C 0.3868(3) 0.4956(3) 1.42156(19) 0.0348(8) Uani 1 1 d . . . C67 C 0.3779(3) 0.5425(3) 1.4889(2) 0.0381(9) Uani 1 1 d . . . H67A H 0.4061 0.6204 1.4948 0.046 Uiso 1 1 calc R . . C68 C 0.3287(3) 0.4777(3) 1.5477(2) 0.0448(10) Uani 1 1 d . . . H68A H 0.3239 0.5113 1.5938 0.054 Uiso 1 1 calc R . . C69 C 0.2863(3) 0.3646(3) 1.5400(2) 0.0437(10) Uani 1 1 d . . . H69A H 0.2528 0.3199 1.5805 0.052 Uiso 1 1 calc R . . C70 C 0.2934(4) 0.3172(3) 1.4725(2) 0.0467(10) Uani 1 1 d . . . H70A H 0.2636 0.2392 1.4667 0.056 Uiso 1 1 calc R . . C71 C 0.3428(3) 0.3811(3) 1.4136(2) 0.0404(9) Uani 1 1 d . . . H71A H 0.3469 0.3472 1.3675 0.048 Uiso 1 1 calc R . . S72 S 0.33208(9) 0.28451(8) 1.15520(5) 0.0425(3) Uani 1 1 d . . . O74 O 0.3922(3) 0.3833(2) 1.11510(16) 0.0630(9) Uani 1 1 d . . . O75 O 0.3024(3) 0.1854(2) 1.11288(19) 0.0734(10) Uani 1 1 d . . . O76 O 0.3780(2) 0.28661(19) 1.22999(14) 0.0442(7) Uani 1 1 d . . . C73 C 0.2028(4) 0.2963(4) 1.1709(3) 0.0610(13) Uani 1 1 d . . . F77 F 0.1353(3) 0.2153(3) 1.2083(2) 0.1203(15) Uani 1 1 d . . . F78 F 0.2229(3) 0.3907(3) 1.20883(18) 0.1067(12) Uani 1 1 d . . . F79 F 0.1509(2) 0.2981(2) 1.10667(15) 0.0741(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0383(18) 0.0397(16) 0.0306(17) -0.0004(13) 0.0001(14) 0.0213(14) N2 0.0395(19) 0.0364(16) 0.0349(18) -0.0042(13) -0.0030(15) 0.0199(14) O3 0.0474(17) 0.0531(16) 0.0375(16) -0.0026(12) -0.0051(13) 0.0203(13) C3 0.045(2) 0.039(2) 0.033(2) 0.0002(17) 0.0072(18) 0.0225(18) O4 0.0438(17) 0.0370(14) 0.0493(17) -0.0034(12) 0.0016(13) 0.0147(12) C5 0.046(3) 0.042(2) 0.052(3) -0.0081(19) 0.008(2) 0.0088(18) C6 0.044(3) 0.046(2) 0.044(2) -0.0112(18) -0.0114(19) 0.0166(18) C7 0.041(3) 0.054(2) 0.049(3) -0.001(2) -0.001(2) 0.0175(19) C8 0.048(3) 0.073(3) 0.067(3) -0.003(3) 0.001(2) 0.023(2) C9 0.067(4) 0.087(4) 0.083(4) 0.013(3) 0.024(3) 0.021(3) C10 0.086(4) 0.065(3) 0.094(4) 0.031(3) 0.025(3) 0.023(3) C11 0.062(3) 0.053(3) 0.068(3) 0.001(2) 0.000(3) 0.022(2) C12 0.037(2) 0.0295(17) 0.0316(19) 0.0007(14) 0.0008(16) 0.0174(15) C13 0.036(2) 0.0398(19) 0.0299(19) -0.0019(15) 0.0004(16) 0.0183(16) O14 0.0443(17) 0.0485(15) 0.0382(15) 0.0058(13) 0.0053(13) 0.0126(12) C14 0.039(2) 0.0323(18) 0.036(2) -0.0003(16) 0.0040(17) 0.0187(16) O15 0.0341(15) 0.0408(13) 0.0436(16) -0.0078(11) -0.0091(12) 0.0137(11) C16 0.037(2) 0.046(2) 0.059(3) -0.0139(19) -0.005(2) 0.0129(18) C17 0.032(2) 0.0343(18) 0.033(2) -0.0031(15) -0.0023(16) 0.0148(15) C18 0.031(2) 0.051(2) 0.036(2) 0.0036(17) 0.0007(17) 0.0165(17) C19 0.038(2) 0.062(2) 0.042(2) 0.005(2) 0.0080(19) 0.0188(19) C20 0.032(2) 0.065(3) 0.050(3) -0.010(2) 0.001(2) 0.0210(19) C21 0.046(3) 0.064(3) 0.053(3) 0.004(2) -0.005(2) 0.030(2) C22 0.039(2) 0.052(2) 0.050(3) 0.0117(19) 0.000(2) 0.0221(19) C23 0.041(2) 0.0375(19) 0.0292(19) 0.0038(15) 0.0015(16) 0.0190(16) C24 0.037(2) 0.0349(18) 0.031(2) 0.0031(15) 0.0008(16) 0.0173(16) C25 0.051(3) 0.0383(19) 0.036(2) 0.0014(16) 0.0005(19) 0.0216(18) C26 0.045(2) 0.0351(18) 0.0268(19) -0.0036(15) 0.0057(17) 0.0150(16) C27 0.053(3) 0.041(2) 0.039(2) 0.0027(17) 0.005(2) 0.0191(18) C28 0.069(3) 0.050(2) 0.031(2) 0.0014(18) 0.016(2) 0.013(2) C29 0.053(3) 0.042(2) 0.053(3) -0.010(2) 0.017(2) 0.0083(19) C30 0.070(3) 0.046(2) 0.062(3) -0.005(2) 0.016(3) 0.029(2) C31 0.058(3) 0.044(2) 0.045(2) 0.0012(18) 0.008(2) 0.025(2) S32 0.0399(6) 0.0362(5) 0.0335(5) 0.0040(4) 0.0038(4) 0.0207(4) O34 0.0416(16) 0.0559(15) 0.0290(14) -0.0010(12) 0.0049(12) 0.0233(12) O35 0.0466(16) 0.0440(14) 0.0344(14) -0.0106(11) -0.0031(12) 0.0225(12) O36 0.062(2) 0.0499(15) 0.0568(18) 0.0154(14) -0.0007(15) 0.0345(14) C33 0.039(2) 0.044(2) 0.043(2) 0.0003(18) -0.0007(19) 0.0253(18) F37 0.0502(15) 0.0428(12) 0.0725(17) 0.0206(11) 0.0002(12) 0.0213(11) F38 0.0473(15) 0.0546(13) 0.0539(15) -0.0039(11) -0.0105(12) 0.0165(11) F39 0.0443(15) 0.0755(15) 0.0520(15) 0.0044(12) 0.0143(12) 0.0296(12) N41 0.0431(19) 0.0370(15) 0.0274(16) -0.0010(12) 0.0005(14) 0.0236(14) N42 0.054(2) 0.0417(17) 0.0351(18) 0.0015(15) 0.0066(17) 0.0294(17) O43 0.069(2) 0.0641(18) 0.0390(17) 0.0058(15) 0.0064(15) 0.0406(16) C43 0.063(3) 0.041(2) 0.033(2) 0.0025(18) 0.016(2) 0.029(2) O44 0.067(2) 0.0569(17) 0.0515(18) 0.0111(14) 0.0177(15) 0.0386(15) C45 0.063(3) 0.066(3) 0.052(3) 0.015(2) 0.010(2) 0.041(2) C46 0.045(3) 0.065(3) 0.038(2) 0.012(2) -0.0004(19) 0.031(2) C47 0.052(3) 0.061(3) 0.046(3) -0.008(2) -0.016(2) 0.030(2) C48 0.039(3) 0.055(2) 0.064(3) 0.011(2) 0.002(2) 0.015(2) C49 0.046(3) 0.074(3) 0.058(3) 0.015(2) 0.014(2) 0.033(2) C50 0.062(3) 0.072(3) 0.050(3) 0.010(2) 0.009(2) 0.035(3) C51 0.050(3) 0.052(2) 0.055(3) 0.006(2) 0.000(2) 0.023(2) C52 0.038(2) 0.0367(18) 0.0291(19) 0.0035(15) 0.0040(16) 0.0193(16) C53 0.039(2) 0.044(2) 0.0270(19) 0.0033(16) 0.0007(16) 0.0205(17) O54 0.0490(18) 0.0688(18) 0.0386(16) 0.0043(13) 0.0045(14) 0.0331(15) C54 0.042(2) 0.042(2) 0.033(2) 0.0081(17) 0.0024(18) 0.0223(17) O55 0.0422(17) 0.0503(15) 0.0395(16) 0.0008(12) -0.0057(13) 0.0203(12) C56 0.042(3) 0.061(3) 0.060(3) 0.004(2) -0.010(2) 0.021(2) C57 0.043(2) 0.0320(18) 0.036(2) 0.0007(15) 0.0011(18) 0.0172(16) C58 0.052(3) 0.061(2) 0.043(2) -0.004(2) 0.005(2) 0.028(2) C59 0.041(3) 0.079(3) 0.050(3) 0.000(2) 0.012(2) 0.017(2) C60 0.036(3) 0.059(3) 0.074(3) -0.001(2) 0.000(2) 0.012(2) C61 0.052(3) 0.048(2) 0.058(3) -0.006(2) -0.010(2) 0.020(2) C62 0.045(3) 0.042(2) 0.041(2) -0.0028(17) 0.0013(19) 0.0169(18) C63 0.040(2) 0.0406(19) 0.034(2) -0.0013(16) 0.0009(17) 0.0219(17) C64 0.044(2) 0.0384(19) 0.030(2) -0.0016(15) 0.0015(17) 0.0227(17) C65 0.043(2) 0.0371(19) 0.035(2) 0.0026(16) 0.0019(18) 0.0202(17) C66 0.041(2) 0.043(2) 0.030(2) 0.0023(16) 0.0036(17) 0.0271(17) C67 0.048(2) 0.0394(19) 0.034(2) -0.0014(16) 0.0019(18) 0.0248(17) C68 0.060(3) 0.061(2) 0.029(2) 0.0036(18) 0.0102(19) 0.040(2) C69 0.051(3) 0.051(2) 0.042(2) 0.0151(19) 0.0158(19) 0.032(2) C70 0.061(3) 0.041(2) 0.048(2) 0.0104(18) 0.019(2) 0.029(2) C71 0.056(3) 0.042(2) 0.031(2) -0.0001(16) 0.0113(18) 0.0275(18) S72 0.0556(7) 0.0452(5) 0.0357(6) -0.0020(4) 0.0016(5) 0.0302(5) O74 0.069(2) 0.0671(18) 0.0426(17) 0.0174(15) 0.0019(15) 0.0177(16) O75 0.089(3) 0.0609(18) 0.083(2) -0.0383(17) -0.032(2) 0.0480(18) O76 0.0612(19) 0.0430(14) 0.0359(15) 0.0066(12) 0.0011(13) 0.0288(13) C73 0.081(4) 0.076(3) 0.044(3) 0.018(2) 0.010(3) 0.050(3) F77 0.069(2) 0.192(4) 0.125(3) 0.105(3) 0.040(2) 0.073(2) F78 0.149(3) 0.143(3) 0.083(2) -0.021(2) -0.003(2) 0.117(3) F79 0.077(2) 0.111(2) 0.0581(17) 0.0186(15) 0.0002(15) 0.0626(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C23 1.319(4) . ? N1 N2 1.383(4) . ? N1 C12 1.482(4) . ? N2 C3 1.394(5) . ? N2 H2N 0.960(19) . ? O3 C3 1.202(4) . ? C3 O4 1.329(4) . ? O4 C5 1.478(5) . ? C5 C6 1.502(6) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C11 1.365(6) . ? C6 C7 1.388(6) . ? C7 C8 1.384(6) . ? C7 H7A 0.9500 . ? C8 C9 1.350(7) . ? C8 H8A 0.9500 . ? C9 C10 1.389(8) . ? C9 H9A 0.9500 . ? C10 C11 1.380(7) . ? C10 H10A 0.9500 . ? C11 H11A 0.9500 . ? C12 C13 1.510(5) . ? C12 C17 1.511(5) . ? C12 H12A 1.0000 . ? C13 C14 1.503(5) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? O14 C14 1.203(4) . ? C14 O15 1.337(4) . ? O15 C16 1.453(5) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C18 1.376(5) . ? C17 C22 1.378(5) . ? C18 C19 1.388(5) . ? C18 H18A 0.9500 . ? C19 C20 1.371(6) . ? C19 H19A 0.9500 . ? C20 C21 1.382(6) . ? C20 H20A 0.9500 . ? C21 C22 1.376(6) . ? C21 H21A 0.9500 . ? C22 H22A 0.9500 . ? C23 C24 1.408(5) . ? C23 H23A 0.9500 . ? C24 C25 1.348(5) . ? C24 H24A 0.9500 . ? C25 C26 1.452(5) . ? C25 H25A 0.9500 . ? C26 C31 1.399(5) . ? C26 C27 1.404(5) . ? C27 C28 1.392(5) . ? C27 H27A 0.9500 . ? C28 C29 1.373(6) . ? C28 H28A 0.9500 . ? C29 C30 1.382(6) . ? C29 H29A 0.9500 . ? C30 C31 1.369(5) . ? C30 H30A 0.9500 . ? C31 H31A 0.9500 . ? S32 O36 1.433(3) . ? S32 O34 1.446(3) . ? S32 O35 1.448(3) . ? S32 C33 1.825(4) . ? C33 F37 1.325(4) . ? C33 F38 1.329(4) . ? C33 F39 1.330(4) . ? N41 C63 1.295(4) . ? N41 N42 1.390(4) . ? N41 C52 1.496(4) . ? N42 C43 1.421(5) . ? N42 H42N 0.936(19) . ? O43 C43 1.180(5) . ? C43 O44 1.340(4) . ? O44 C45 1.482(5) . ? C45 C46 1.509(6) . ? C45 H45A 0.9900 . ? C45 H45B 0.9900 . ? C46 C51 1.379(6) . ? C46 C47 1.406(6) . ? C47 C48 1.378(6) . ? C47 H47A 0.9500 . ? C48 C49 1.390(6) . ? C48 H48A 0.9500 . ? C49 C50 1.361(6) . ? C49 H49A 0.9500 . ? C50 C51 1.353(6) . ? C50 H50A 0.9500 . ? C51 H51A 0.9500 . ? C52 C57 1.515(5) . ? C52 C53 1.518(5) . ? C52 H52A 1.0000 . ? C53 C54 1.503(5) . ? C53 H53A 0.9900 . ? C53 H53B 0.9900 . ? O54 C54 1.209(4) . ? C54 O55 1.346(4) . ? O55 C56 1.445(5) . ? C56 H56A 0.9800 . ? C56 H56B 0.9800 . ? C56 H56C 0.9800 . ? C57 C62 1.389(5) . ? C57 C58 1.392(5) . ? C58 C59 1.400(6) . ? C58 H58A 0.9500 . ? C59 C60 1.365(6) . ? C59 H59A 0.9500 . ? C60 C61 1.382(6) . ? C60 H60A 0.9500 . ? C61 C62 1.382(6) . ? C61 H61A 0.9500 . ? C62 H62A 0.9500 . ? C63 C64 1.415(5) . ? C63 H63A 0.9500 . ? C64 C65 1.350(5) . ? C64 H64A 0.9500 . ? C65 C66 1.461(5) . ? C65 H65A 0.9500 . ? C66 C67 1.383(5) . ? C66 C71 1.394(5) . ? C67 C68 1.378(5) . ? C67 H67A 0.9500 . ? C68 C69 1.378(5) . ? C68 H68A 0.9500 . ? C69 C70 1.379(5) . ? C69 H69A 0.9500 . ? C70 C71 1.376(5) . ? C70 H70A 0.9500 . ? C71 H71A 0.9500 . ? S72 O75 1.412(3) . ? S72 O74 1.447(3) . ? S72 O76 1.450(3) . ? S72 C73 1.812(5) . ? C73 F77 1.298(5) . ? C73 F79 1.328(5) . ? C73 F78 1.340(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C23 N1 N2 121.8(3) . . ? C23 N1 C12 121.8(3) . . ? N2 N1 C12 116.4(3) . . ? N1 N2 C3 117.3(3) . . ? N1 N2 H2N 112(2) . . ? C3 N2 H2N 129(2) . . ? O3 C3 O4 127.8(4) . . ? O3 C3 N2 124.6(3) . . ? O4 C3 N2 107.6(3) . . ? C3 O4 C5 115.0(3) . . ? O4 C5 C6 110.0(3) . . ? O4 C5 H5A 109.7 . . ? C6 C5 H5A 109.7 . . ? O4 C5 H5B 109.7 . . ? C6 C5 H5B 109.7 . . ? H5A C5 H5B 108.2 . . ? C11 C6 C7 117.8(4) . . ? C11 C6 C5 121.6(4) . . ? C7 C6 C5 120.6(4) . . ? C8 C7 C6 121.5(4) . . ? C8 C7 H7A 119.3 . . ? C6 C7 H7A 119.3 . . ? C9 C8 C7 119.6(5) . . ? C9 C8 H8A 120.2 . . ? C7 C8 H8A 120.2 . . ? C8 C9 C10 120.3(5) . . ? C8 C9 H9A 119.9 . . ? C10 C9 H9A 119.9 . . ? C11 C10 C9 119.4(5) . . ? C11 C10 H10A 120.3 . . ? C9 C10 H10A 120.3 . . ? C6 C11 C10 121.4(5) . . ? C6 C11 H11A 119.3 . . ? C10 C11 H11A 119.3 . . ? N1 C12 C13 109.1(3) . . ? N1 C12 C17 111.2(3) . . ? C13 C12 C17 115.2(3) . . ? N1 C12 H12A 107.0 . . ? C13 C12 H12A 107.0 . . ? C17 C12 H12A 107.0 . . ? C14 C13 C12 113.6(3) . . ? C14 C13 H13A 108.8 . . ? C12 C13 H13A 108.8 . . ? C14 C13 H13B 108.8 . . ? C12 C13 H13B 108.8 . . ? H13A C13 H13B 107.7 . . ? O14 C14 O15 123.9(3) . . ? O14 C14 C13 124.9(3) . . ? O15 C14 C13 111.1(3) . . ? C14 O15 C16 115.6(3) . . ? O15 C16 H16A 109.5 . . ? O15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C18 C17 C22 119.4(4) . . ? C18 C17 C12 122.9(3) . . ? C22 C17 C12 117.7(3) . . ? C17 C18 C19 119.8(4) . . ? C17 C18 H18A 120.1 . . ? C19 C18 H18A 120.1 . . ? C20 C19 C18 121.0(4) . . ? C20 C19 H19A 119.5 . . ? C18 C19 H19A 119.5 . . ? C19 C20 C21 118.8(4) . . ? C19 C20 H20A 120.6 . . ? C21 C20 H20A 120.6 . . ? C22 C21 C20 120.7(4) . . ? C22 C21 H21A 119.7 . . ? C20 C21 H21A 119.7 . . ? C21 C22 C17 120.4(4) . . ? C21 C22 H22A 119.8 . . ? C17 C22 H22A 119.8 . . ? N1 C23 C24 124.8(3) . . ? N1 C23 H23A 117.6 . . ? C24 C23 H23A 117.6 . . ? C25 C24 C23 118.2(3) . . ? C25 C24 H24A 120.9 . . ? C23 C24 H24A 120.9 . . ? C24 C25 C26 126.6(3) . . ? C24 C25 H25A 116.7 . . ? C26 C25 H25A 116.7 . . ? C31 C26 C27 118.2(3) . . ? C31 C26 C25 123.4(3) . . ? C27 C26 C25 118.3(3) . . ? C28 C27 C26 120.4(4) . . ? C28 C27 H27A 119.8 . . ? C26 C27 H27A 119.8 . . ? C29 C28 C27 119.7(4) . . ? C29 C28 H28A 120.2 . . ? C27 C28 H28A 120.2 . . ? C28 C29 C30 120.7(4) . . ? C28 C29 H29A 119.6 . . ? C30 C29 H29A 119.7 . . ? C31 C30 C29 120.0(4) . . ? C31 C30 H30A 120.0 . . ? C29 C30 H30A 120.0 . . ? C30 C31 C26 121.0(4) . . ? C30 C31 H31A 119.5 . . ? C26 C31 H31A 119.5 . . ? O36 S32 O34 115.57(16) . . ? O36 S32 O35 115.53(16) . . ? O34 S32 O35 113.51(16) . . ? O36 S32 C33 104.50(17) . . ? O34 S32 C33 102.42(16) . . ? O35 S32 C33 102.95(17) . . ? F37 C33 F38 107.6(3) . . ? F37 C33 F39 108.2(3) . . ? F38 C33 F39 108.0(3) . . ? F37 C33 S32 110.3(3) . . ? F38 C33 S32 111.6(3) . . ? F39 C33 S32 111.1(2) . . ? C63 N41 N42 121.4(3) . . ? C63 N41 C52 122.9(3) . . ? N42 N41 C52 115.7(3) . . ? N41 N42 C43 115.6(3) . . ? N41 N42 H42N 109(2) . . ? C43 N42 H42N 128(2) . . ? O43 C43 O44 129.9(4) . . ? O43 C43 N42 124.7(3) . . ? O44 C43 N42 105.4(4) . . ? C43 O44 C45 112.0(4) . . ? O44 C45 C46 108.5(3) . . ? O44 C45 H45A 110.0 . . ? C46 C45 H45A 110.0 . . ? O44 C45 H45B 110.0 . . ? C46 C45 H45B 110.0 . . ? H45A C45 H45B 108.4 . . ? C51 C46 C47 119.6(4) . . ? C51 C46 C45 120.0(4) . . ? C47 C46 C45 120.3(4) . . ? C48 C47 C46 119.4(4) . . ? C48 C47 H47A 120.3 . . ? C46 C47 H47A 120.3 . . ? C47 C48 C49 118.7(4) . . ? C47 C48 H48A 120.7 . . ? C49 C48 H48A 120.7 . . ? C50 C49 C48 121.6(4) . . ? C50 C49 H49A 119.2 . . ? C48 C49 H49A 119.2 . . ? C51 C50 C49 119.9(4) . . ? C51 C50 H50A 120.0 . . ? C49 C50 H50A 120.0 . . ? C50 C51 C46 120.7(4) . . ? C50 C51 H51A 119.7 . . ? C46 C51 H51A 119.7 . . ? N41 C52 C57 109.4(3) . . ? N41 C52 C53 107.9(3) . . ? C57 C52 C53 115.5(3) . . ? N41 C52 H52A 108.0 . . ? C57 C52 H52A 108.0 . . ? C53 C52 H52A 108.0 . . ? C54 C53 C52 112.9(3) . . ? C54 C53 H53A 109.0 . . ? C52 C53 H53A 109.0 . . ? C54 C53 H53B 109.0 . . ? C52 C53 H53B 109.0 . . ? H53A C53 H53B 107.8 . . ? O54 C54 O55 124.0(4) . . ? O54 C54 C53 125.2(4) . . ? O55 C54 C53 110.8(3) . . ? C54 O55 C56 115.7(3) . . ? O55 C56 H56A 109.5 . . ? O55 C56 H56B 109.5 . . ? H56A C56 H56B 109.5 . . ? O55 C56 H56C 109.5 . . ? H56A C56 H56C 109.5 . . ? H56B C56 H56C 109.5 . . ? C62 C57 C58 119.1(4) . . ? C62 C57 C52 118.8(3) . . ? C58 C57 C52 122.1(3) . . ? C57 C58 C59 119.8(4) . . ? C57 C58 H58A 120.1 . . ? C59 C58 H58A 120.1 . . ? C60 C59 C58 120.8(4) . . ? C60 C59 H59A 119.6 . . ? C58 C59 H59A 119.6 . . ? C59 C60 C61 119.3(4) . . ? C59 C60 H60A 120.4 . . ? C61 C60 H60A 120.4 . . ? C62 C61 C60 121.1(4) . . ? C62 C61 H61A 119.5 . . ? C60 C61 H61A 119.5 . . ? C61 C62 C57 120.0(4) . . ? C61 C62 H62A 120.0 . . ? C57 C62 H62A 120.0 . . ? N41 C63 C64 125.9(3) . . ? N41 C63 H63A 117.0 . . ? C64 C63 H63A 117.0 . . ? C65 C64 C63 118.2(3) . . ? C65 C64 H64A 120.9 . . ? C63 C64 H64A 120.9 . . ? C64 C65 C66 126.7(3) . . ? C64 C65 H65A 116.6 . . ? C66 C65 H65A 116.6 . . ? C67 C66 C71 118.6(3) . . ? C67 C66 C65 118.2(3) . . ? C71 C66 C65 123.1(3) . . ? C68 C67 C66 120.8(3) . . ? C68 C67 H67A 119.6 . . ? C66 C67 H67A 119.6 . . ? C67 C68 C69 120.4(4) . . ? C67 C68 H68A 119.8 . . ? C69 C68 H68A 119.8 . . ? C68 C69 C70 119.1(3) . . ? C68 C69 H69A 120.5 . . ? C70 C69 H69A 120.5 . . ? C71 C70 C69 121.0(3) . . ? C71 C70 H70A 119.5 . . ? C69 C70 H70A 119.5 . . ? C70 C71 C66 120.0(3) . . ? C70 C71 H71A 120.0 . . ? C66 C71 H71A 120.0 . . ? O75 S72 O74 114.5(2) . . ? O75 S72 O76 115.91(17) . . ? O74 S72 O76 113.59(18) . . ? O75 S72 C73 105.7(2) . . ? O74 S72 C73 101.7(2) . . ? O76 S72 C73 103.31(19) . . ? F77 C73 F79 107.8(4) . . ? F77 C73 F78 108.2(4) . . ? F79 C73 F78 107.4(3) . . ? F77 C73 S72 112.3(3) . . ? F79 C73 S72 110.8(3) . . ? F78 C73 S72 110.1(4) . . ? 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 C23 N1 N2 C3 -68.4(4) . . . . ? C12 N1 N2 C3 113.3(3) . . . . ? N1 N2 C3 O3 -4.9(5) . . . . ? N1 N2 C3 O4 174.5(3) . . . . ? O3 C3 O4 C5 -8.5(5) . . . . ? N2 C3 O4 C5 172.2(3) . . . . ? C3 O4 C5 C6 -93.5(4) . . . . ? O4 C5 C6 C11 -110.6(4) . . . . ? O4 C5 C6 C7 68.4(5) . . . . ? C11 C6 C7 C8 -0.6(6) . . . . ? C5 C6 C7 C8 -179.5(4) . . . . ? C6 C7 C8 C9 0.7(7) . . . . ? C7 C8 C9 C10 -0.7(8) . . . . ? C8 C9 C10 C11 0.7(9) . . . . ? C7 C6 C11 C10 0.5(7) . . . . ? C5 C6 C11 C10 179.5(5) . . . . ? C9 C10 C11 C6 -0.6(9) . . . . ? C23 N1 C12 C13 -114.7(4) . . . . ? N2 N1 C12 C13 63.6(4) . . . . ? C23 N1 C12 C17 117.2(4) . . . . ? N2 N1 C12 C17 -64.5(4) . . . . ? N1 C12 C13 C14 66.4(4) . . . . ? C17 C12 C13 C14 -167.7(3) . . . . ? C12 C13 C14 O14 9.5(5) . . . . ? C12 C13 C14 O15 -173.7(3) . . . . ? O14 C14 O15 C16 -0.9(5) . . . . ? C13 C14 O15 C16 -177.7(3) . . . . ? N1 C12 C17 C18 106.3(4) . . . . ? C13 C12 C17 C18 -18.4(5) . . . . ? N1 C12 C17 C22 -75.7(4) . . . . ? C13 C12 C17 C22 159.6(3) . . . . ? C22 C17 C18 C19 -0.5(6) . . . . ? C12 C17 C18 C19 177.5(3) . . . . ? C17 C18 C19 C20 -0.5(6) . . . . ? C18 C19 C20 C21 0.4(6) . . . . ? C19 C20 C21 C22 0.6(6) . . . . ? C20 C21 C22 C17 -1.6(6) . . . . ? C18 C17 C22 C21 1.5(6) . . . . ? C12 C17 C22 C21 -176.5(4) . . . . ? N2 N1 C23 C24 -6.0(6) . . . . ? C12 N1 C23 C24 172.2(3) . . . . ? N1 C23 C24 C25 177.5(4) . . . . ? C23 C24 C25 C26 174.1(4) . . . . ? C24 C25 C26 C31 -14.6(6) . . . . ? C24 C25 C26 C27 169.2(4) . . . . ? C31 C26 C27 C28 1.8(6) . . . . ? C25 C26 C27 C28 178.2(4) . . . . ? C26 C27 C28 C29 -0.4(6) . . . . ? C27 C28 C29 C30 -1.3(7) . . . . ? C28 C29 C30 C31 1.6(7) . . . . ? C29 C30 C31 C26 -0.2(7) . . . . ? C27 C26 C31 C30 -1.5(6) . . . . ? C25 C26 C31 C30 -177.7(4) . . . . ? O36 S32 C33 F37 -174.3(3) . . . . ? O34 S32 C33 F37 -53.4(3) . . . . ? O35 S32 C33 F37 64.6(3) . . . . ? O36 S32 C33 F38 -54.7(3) . . . . ? O34 S32 C33 F38 66.2(3) . . . . ? O35 S32 C33 F38 -175.8(2) . . . . ? O36 S32 C33 F39 65.8(3) . . . . ? O34 S32 C33 F39 -173.3(2) . . . . ? O35 S32 C33 F39 -55.3(3) . . . . ? C63 N41 N42 C43 -67.8(5) . . . . ? C52 N41 N42 C43 112.7(3) . . . . ? N41 N42 C43 O43 -7.4(6) . . . . ? N41 N42 C43 O44 170.8(3) . . . . ? O43 C43 O44 C45 -15.5(6) . . . . ? N42 C43 O44 C45 166.3(3) . . . . ? C43 O44 C45 C46 -97.8(4) . . . . ? O44 C45 C46 C51 -102.1(4) . . . . ? O44 C45 C46 C47 74.3(5) . . . . ? C51 C46 C47 C48 0.1(6) . . . . ? C45 C46 C47 C48 -176.3(4) . . . . ? C46 C47 C48 C49 1.3(6) . . . . ? C47 C48 C49 C50 -2.1(7) . . . . ? C48 C49 C50 C51 1.4(7) . . . . ? C49 C50 C51 C46 0.0(7) . . . . ? C47 C46 C51 C50 -0.8(6) . . . . ? C45 C46 C51 C50 175.6(4) . . . . ? C63 N41 C52 C57 119.4(4) . . . . ? N42 N41 C52 C57 -61.0(4) . . . . ? C63 N41 C52 C53 -114.2(4) . . . . ? N42 N41 C52 C53 65.3(4) . . . . ? N41 C52 C53 C54 62.2(4) . . . . ? C57 C52 C53 C54 -175.1(3) . . . . ? C52 C53 C54 O54 12.3(5) . . . . ? C52 C53 C54 O55 -169.0(3) . . . . ? O54 C54 O55 C56 -3.5(5) . . . . ? C53 C54 O55 C56 177.8(3) . . . . ? N41 C52 C57 C62 -58.4(4) . . . . ? C53 C52 C57 C62 179.7(3) . . . . ? N41 C52 C57 C58 122.1(3) . . . . ? C53 C52 C57 C58 0.3(5) . . . . ? C62 C57 C58 C59 -0.3(5) . . . . ? C52 C57 C58 C59 179.2(3) . . . . ? C57 C58 C59 C60 1.3(6) . . . . ? C58 C59 C60 C61 -1.2(7) . . . . ? C59 C60 C61 C62 0.2(6) . . . . ? C60 C61 C62 C57 0.8(6) . . . . ? C58 C57 C62 C61 -0.7(5) . . . . ? C52 C57 C62 C61 179.8(3) . . . . ? N42 N41 C63 C64 -4.3(6) . . . . ? C52 N41 C63 C64 175.2(3) . . . . ? N41 C63 C64 C65 172.3(4) . . . . ? C63 C64 C65 C66 179.9(4) . . . . ? C64 C65 C66 C67 164.4(4) . . . . ? C64 C65 C66 C71 -14.9(6) . . . . ? C71 C66 C67 C68 1.4(6) . . . . ? C65 C66 C67 C68 -177.9(3) . . . . ? C66 C67 C68 C69 -0.7(6) . . . . ? C67 C68 C69 C70 -0.4(6) . . . . ? C68 C69 C70 C71 0.7(6) . . . . ? C69 C70 C71 C66 0.0(6) . . . . ? C67 C66 C71 C70 -1.1(6) . . . . ? C65 C66 C71 C70 178.2(4) . . . . ? O75 S72 C73 F77 61.4(4) . . . . ? O74 S72 C73 F77 -178.7(4) . . . . ? O76 S72 C73 F77 -60.8(4) . . . . ? O75 S72 C73 F79 -59.2(4) . . . . ? O74 S72 C73 F79 60.7(4) . . . . ? O76 S72 C73 F79 178.6(3) . . . . ? O75 S72 C73 F78 -177.9(3) . . . . ? O74 S72 C73 F78 -58.0(3) . . . . ? O76 S72 C73 F78 60.0(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2N O34 0.960(19) 1.91(2) 2.831(4) 160(3) . N42 H42N O74 0.936(19) 1.85(2) 2.766(5) 165(3) . _diffrn_measured_fraction_theta_max 0.954 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.963 _refine_diff_density_max 0.577 _refine_diff_density_min -0.451 _refine_diff_density_rms 0.068 _database_code_depnum_ccdc_archive 'CCDC 925705'