# Electronic Supplementary Material (ESI) for Chemical Science # 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_2 _database_code_depnum_ccdc_archive 'CCDC 923531' #TrackingRef '17579_web_deposit_cif_file_0_RoyMcBurney_1360161219.6d.cif' _chemical_formula_sum 'C19 H21 N O3' _chemical_formula_moiety 'C19 H21 N O3' _chemical_formula_weight 311.38 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,-Y,-Z #------------------------------------------------------------------------------ _cell_length_a 6.229(3) _cell_length_b 11.758(7) _cell_length_c 12.009(7) _cell_angle_alpha 88.61(4) _cell_angle_beta 77.64(6) _cell_angle_gamma 83.80(4) _cell_volume 854.1(8) _cell_formula_units_Z 2 _cell_measurement_reflns_used 564 _cell_measurement_theta_min 41.11 _cell_measurement_theta_max 68.25 _cell_measurement_temperature 173 #------------------------------------------------------------------------------ _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.120 _exptl_crystal_size_mid 0.030 _exptl_crystal_size_min 0.030 _exptl_crystal_density_diffrn 1.211 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 332.00 _exptl_absorpt_coefficient_mu 0.659 _exptl_absorpt_correction_type none #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 173 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54187 _diffrn_measurement_device_type ? _diffrn_reflns_number 8939 _diffrn_reflns_av_R_equivalents 0.1235 _diffrn_reflns_theta_max 67.93 _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 67.00 _diffrn_measured_fraction_theta_full 0.982 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 12 _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 3049 _reflns_number_gt 1806 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0752 _refine_ls_wR_factor_ref 0.2094 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 3049 _refine_ls_number_parameters 209 _refine_ls_goodness_of_fit_ref 0.899 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.1263P)^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 0.280 _refine_diff_density_min -0.310 _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.028(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 O2 O 0.4816(3) 0.02741(15) 0.81937(14) 0.0645(6) Uani 1.0 2 d . . . O3 O 0.8515(4) 0.01362(19) 0.81830(18) 0.0820(7) Uani 1.0 2 d . . . O4 O 0.5870(3) 0.11240(15) 0.94959(15) 0.0681(6) Uani 1.0 2 d . . . N1 N 0.5398(4) -0.04544(18) 0.72036(18) 0.0627(6) Uani 1.0 2 d . . . C3 C 0.6646(5) 0.0470(3) 0.8575(3) 0.0643(7) Uani 1.0 2 d . . . C5 C 0.7584(6) 0.1592(3) 0.9965(3) 0.0707(8) Uani 1.0 2 d . . . C6 C 0.8246(5) 0.2658(2) 0.9343(2) 0.0601(7) Uani 1.0 2 d . . . C7 C 1.0426(5) 0.2809(3) 0.8889(3) 0.0693(8) Uani 1.0 2 d . . . C8 C 1.1003(5) 0.3823(3) 0.8342(3) 0.0660(7) Uani 1.0 2 d . . . C9 C 0.9424(5) 0.4716(2) 0.8210(2) 0.0574(7) Uani 1.0 2 d . . . C10 C 0.7228(5) 0.4546(3) 0.8675(3) 0.0696(8) Uani 1.0 2 d . . . C11 C 0.6654(5) 0.3549(3) 0.9237(3) 0.0700(8) Uani 1.0 2 d . . . C12 C 0.9996(5) 0.5806(3) 0.7541(3) 0.0645(7) Uani 1.0 2 d . . . C13 C 0.9680(7) 0.5643(3) 0.6330(3) 0.0916(11) Uani 1.0 2 d . . . C14 C 1.2367(6) 0.6050(3) 0.7524(4) 0.0974(11) Uani 1.0 2 d . . . C15 C 0.8469(6) 0.6861(3) 0.8055(3) 0.0865(10) Uani 1.0 2 d . . . C16 C 0.3642(5) -0.0499(2) 0.6821(3) 0.0619(7) Uani 1.0 2 d . . . C17 C 0.3723(5) -0.1181(2) 0.5808(2) 0.0589(7) Uani 1.0 2 d . . . C18 C 0.5654(5) -0.1829(3) 0.5259(3) 0.0714(8) Uani 1.0 2 d . . . C19 C 0.5683(6) -0.2442(3) 0.4298(3) 0.0800(9) Uani 1.0 2 d . . . C20 C 0.3787(6) -0.2420(3) 0.3857(3) 0.0766(9) Uani 1.0 2 d . . . C21 C 0.1869(5) -0.1779(3) 0.4395(3) 0.0746(8) Uani 1.0 2 d . . . C22 C 0.1834(5) -0.1169(3) 0.5372(3) 0.0646(7) Uani 1.0 2 d . . . H5A H 0.8890 0.1017 0.9894 0.0849 Uiso 1.0 2 calc R . . H5B H 0.7014 0.1764 1.0784 0.0849 Uiso 1.0 2 calc R . . H7 H 1.1550 0.2212 0.8950 0.0831 Uiso 1.0 2 calc R . . H8 H 1.2521 0.3908 0.8051 0.0792 Uiso 1.0 2 calc R . . H10 H 0.6095 0.5135 0.8602 0.0835 Uiso 1.0 2 calc R . . H11 H 0.5143 0.3472 0.9556 0.0840 Uiso 1.0 2 calc R . . H13A H 0.8144 0.5512 0.6354 0.1099 Uiso 1.0 2 calc R . . H13B H 1.0668 0.4983 0.5979 0.1099 Uiso 1.0 2 calc R . . H13C H 1.0027 0.6331 0.5878 0.1099 Uiso 1.0 2 calc R . . H14A H 1.3399 0.5408 0.7167 0.1168 Uiso 1.0 2 calc R . . H14B H 1.2542 0.6147 0.8307 0.1168 Uiso 1.0 2 calc R . . H14C H 1.2677 0.6751 0.7089 0.1168 Uiso 1.0 2 calc R . . H15A H 0.8615 0.6968 0.8841 0.1037 Uiso 1.0 2 calc R . . H15B H 0.6935 0.6751 0.8050 0.1037 Uiso 1.0 2 calc R . . H15C H 0.8883 0.7539 0.7603 0.1037 Uiso 1.0 2 calc R . . H16 H 0.2290 -0.0090 0.7194 0.0743 Uiso 1.0 2 calc R . . H18 H 0.6956 -0.1846 0.5553 0.0857 Uiso 1.0 2 calc R . . H19 H 0.7003 -0.2883 0.3931 0.0960 Uiso 1.0 2 calc R . . H20 H 0.3810 -0.2845 0.3191 0.0920 Uiso 1.0 2 calc R . . H21 H 0.0574 -0.1756 0.4093 0.0895 Uiso 1.0 2 calc R . . H22 H 0.0505 -0.0739 0.5745 0.0775 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 O2 0.0635(11) 0.0619(11) 0.0680(11) -0.0087(8) -0.0129(9) -0.0026(8) O3 0.0634(13) 0.0882(15) 0.0942(15) -0.0044(11) -0.0161(11) -0.0177(12) O4 0.0774(12) 0.0564(10) 0.0721(11) -0.0147(9) -0.0154(9) -0.0029(8) N1 0.0687(14) 0.0534(12) 0.0647(12) -0.0048(10) -0.0117(11) -0.0018(9) C3 0.0759(18) 0.0507(14) 0.0676(15) -0.0113(12) -0.0162(14) 0.0040(11) C5 0.089(2) 0.0588(15) 0.0706(16) -0.0172(13) -0.0271(15) 0.0046(12) C6 0.0715(16) 0.0533(14) 0.0583(13) -0.0068(11) -0.0198(12) 0.0001(10) C7 0.0707(17) 0.0559(15) 0.0784(17) 0.0045(12) -0.0155(14) 0.0050(12) C8 0.0596(15) 0.0629(15) 0.0738(16) -0.0037(12) -0.0123(13) 0.0035(12) C9 0.0662(15) 0.0546(14) 0.0557(13) -0.0085(11) -0.0215(12) 0.0010(10) C10 0.0616(16) 0.0594(16) 0.0912(19) -0.0034(12) -0.0270(14) 0.0118(13) C11 0.0641(16) 0.0628(16) 0.0850(18) -0.0111(12) -0.0186(14) 0.0085(14) C12 0.0692(16) 0.0601(15) 0.0700(15) -0.0111(12) -0.0263(13) 0.0081(12) C13 0.134(3) 0.076(2) 0.0703(17) -0.0184(19) -0.0315(19) 0.0131(15) C14 0.088(3) 0.081(3) 0.132(3) -0.0245(18) -0.038(3) 0.029(2) C15 0.108(3) 0.0570(16) 0.095(2) -0.0117(16) -0.0219(19) 0.0041(15) C16 0.0617(15) 0.0536(14) 0.0701(15) -0.0059(11) -0.0137(13) 0.0055(11) C17 0.0633(15) 0.0497(13) 0.0630(14) -0.0074(11) -0.0117(12) 0.0079(11) C18 0.0660(17) 0.0691(17) 0.0797(17) -0.0067(13) -0.0166(14) -0.0028(14) C19 0.0727(18) 0.079(2) 0.0867(19) -0.0006(15) -0.0152(16) -0.0130(16) C20 0.088(2) 0.0701(18) 0.0740(17) -0.0166(15) -0.0172(16) -0.0031(14) C21 0.0752(18) 0.0756(18) 0.0775(18) -0.0143(14) -0.0238(15) 0.0056(14) C22 0.0604(15) 0.0610(15) 0.0725(15) -0.0056(11) -0.0152(13) 0.0057(12) #============================================================================== _computing_data_collection 'CrystalClear-SM Expert 2.1 b6 (Rigaku, 2011)' _computing_cell_refinement 'CrystalClear-SM Expert 2.1 b6' _computing_data_reduction 'CrystalClear-SM Expert 2.1 b6' _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 O2 N1 1.441(3) yes . . O2 C3 1.359(4) yes . . O3 C3 1.186(4) yes . . O4 C3 1.335(4) yes . . O4 C5 1.469(4) yes . . N1 C16 1.281(4) yes . . C5 C6 1.496(4) yes . . C6 C7 1.379(4) yes . . C6 C11 1.385(4) yes . . C7 C8 1.391(4) yes . . C8 C9 1.389(4) yes . . C9 C10 1.396(4) yes . . C9 C12 1.530(4) yes . . C10 C11 1.382(4) yes . . C12 C13 1.528(5) yes . . C12 C14 1.530(5) yes . . C12 C15 1.535(4) yes . . C16 C17 1.461(4) yes . . C17 C18 1.396(4) yes . . C17 C22 1.385(5) yes . . C18 C19 1.372(5) yes . . C19 C20 1.391(5) yes . . C20 C21 1.383(4) yes . . C21 C22 1.385(5) yes . . C5 H5A 0.990 no . . C5 H5B 0.990 no . . C7 H7 0.950 no . . C8 H8 0.950 no . . C10 H10 0.950 no . . C11 H11 0.950 no . . C13 H13A 0.980 no . . C13 H13B 0.980 no . . C13 H13C 0.980 no . . C14 H14A 0.980 no . . C14 H14B 0.980 no . . C14 H14C 0.980 no . . C15 H15A 0.980 no . . C15 H15B 0.980 no . . C15 H15C 0.980 no . . C16 H16 0.950 no . . C18 H18 0.950 no . . C19 H19 0.950 no . . C20 H20 0.950 no . . C21 H21 0.950 no . . C22 H22 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 N1 O2 C3 110.79(18) yes . . . C3 O4 C5 114.4(3) yes . . . O2 N1 C16 107.29(19) yes . . . O2 C3 O3 128.1(3) yes . . . O2 C3 O4 104.4(3) yes . . . O3 C3 O4 127.5(3) yes . . . O4 C5 C6 110.3(3) yes . . . C5 C6 C7 122.1(3) yes . . . C5 C6 C11 120.0(3) yes . . . C7 C6 C11 117.9(3) yes . . . C6 C7 C8 121.0(3) yes . . . C7 C8 C9 121.9(3) yes . . . C8 C9 C10 116.2(3) yes . . . C8 C9 C12 123.0(3) yes . . . C10 C9 C12 120.7(3) yes . . . C9 C10 C11 122.0(3) yes . . . C6 C11 C10 121.0(3) yes . . . C9 C12 C13 107.4(3) yes . . . C9 C12 C14 111.6(3) yes . . . C9 C12 C15 112.0(3) yes . . . C13 C12 C14 110.6(3) yes . . . C13 C12 C15 108.2(3) yes . . . C14 C12 C15 107.1(3) yes . . . N1 C16 C17 119.8(3) yes . . . C16 C17 C18 122.0(3) yes . . . C16 C17 C22 118.9(3) yes . . . C18 C17 C22 119.1(3) yes . . . C17 C18 C19 120.4(3) yes . . . C18 C19 C20 120.2(3) yes . . . C19 C20 C21 119.7(3) yes . . . C20 C21 C22 120.1(3) yes . . . C17 C22 C21 120.4(3) yes . . . O4 C5 H5A 109.585 no . . . O4 C5 H5B 109.587 no . . . C6 C5 H5A 109.582 no . . . C6 C5 H5B 109.579 no . . . H5A C5 H5B 108.124 no . . . C6 C7 H7 119.502 no . . . C8 C7 H7 119.504 no . . . C7 C8 H8 119.057 no . . . C9 C8 H8 119.050 no . . . C9 C10 H10 119.005 no . . . C11 C10 H10 119.005 no . . . C6 C11 H11 119.483 no . . . C10 C11 H11 119.488 no . . . C12 C13 H13A 109.471 no . . . C12 C13 H13B 109.471 no . . . C12 C13 H13C 109.468 no . . . H13A C13 H13B 109.466 no . . . H13A C13 H13C 109.475 no . . . H13B C13 H13C 109.476 no . . . C12 C14 H14A 109.469 no . . . C12 C14 H14B 109.466 no . . . C12 C14 H14C 109.468 no . . . H14A C14 H14B 109.468 no . . . H14A C14 H14C 109.478 no . . . H14B C14 H14C 109.478 no . . . C12 C15 H15A 109.472 no . . . C12 C15 H15B 109.469 no . . . C12 C15 H15C 109.469 no . . . H15A C15 H15B 109.470 no . . . H15A C15 H15C 109.471 no . . . H15B C15 H15C 109.477 no . . . N1 C16 H16 120.075 no . . . C17 C16 H16 120.084 no . . . C17 C18 H18 119.781 no . . . C19 C18 H18 119.774 no . . . C18 C19 H19 119.886 no . . . C20 C19 H19 119.878 no . . . C19 C20 H20 120.162 no . . . C21 C20 H20 120.166 no . . . C20 C21 H21 119.945 no . . . C22 C21 H21 119.949 no . . . C17 C22 H22 119.798 no . . . C21 C22 H22 119.806 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 N1 O2 C3 O3 1.3(4) no . . . . N1 O2 C3 O4 -178.61(16) no . . . . C3 O2 N1 C16 -173.10(17) no . . . . C3 O4 C5 C6 83.8(3) no . . . . C5 O4 C3 O2 -171.39(18) no . . . . C5 O4 C3 O3 8.7(4) no . . . . O2 N1 C16 C17 179.93(17) no . . . . O4 C5 C6 C7 -128.4(3) no . . . . O4 C5 C6 C11 53.5(3) no . . . . C5 C6 C7 C8 -178.1(3) no . . . . C5 C6 C11 C10 179.4(3) no . . . . C7 C6 C11 C10 1.2(4) no . . . . C11 C6 C7 C8 0.0(4) no . . . . C6 C7 C8 C9 -1.2(5) no . . . . C7 C8 C9 C10 1.2(4) no . . . . C7 C8 C9 C12 -175.6(3) no . . . . C8 C9 C10 C11 0.1(4) no . . . . C8 C9 C12 C13 95.1(3) no . . . . C8 C9 C12 C14 -26.2(4) no . . . . C8 C9 C12 C15 -146.2(3) no . . . . C10 C9 C12 C13 -81.5(3) no . . . . C10 C9 C12 C14 157.2(3) no . . . . C10 C9 C12 C15 37.2(4) no . . . . C12 C9 C10 C11 176.9(3) no . . . . C9 C10 C11 C6 -1.3(5) no . . . . N1 C16 C17 C18 2.5(4) no . . . . N1 C16 C17 C22 -176.5(2) no . . . . C16 C17 C18 C19 -178.7(2) no . . . . C16 C17 C22 C21 178.1(2) no . . . . C18 C17 C22 C21 -0.9(4) no . . . . C22 C17 C18 C19 0.3(4) no . . . . C17 C18 C19 C20 0.2(5) no . . . . C18 C19 C20 C21 -0.1(5) no . . . . C19 C20 C21 C22 -0.6(5) no . . . . C20 C21 C22 C17 1.1(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 O2 C5 3.493(5) no . . O2 C17 3.595(4) no . . O3 N1 2.635(4) no . . O3 C5 2.698(4) no . . O3 C6 3.280(4) no . . O4 N1 3.438(4) no . . O4 C7 3.573(4) no . . O4 C11 2.942(4) no . . N1 C18 2.839(4) no . . C3 C6 3.087(5) no . . C3 C16 3.391(5) no . . C6 C9 2.835(4) no . . C7 C10 2.742(4) no . . C8 C11 2.743(4) no . . C8 C13 3.365(5) no . . C8 C14 2.922(5) no . . C10 C13 3.215(5) no . . C10 C15 2.944(5) no . . C17 C20 2.779(5) no . . C18 C21 2.766(5) no . . C19 C22 2.766(4) no . . O2 O4 3.163(3) no . 2_657 O2 C5 3.316(4) no . 2_657 O2 C20 3.528(4) no . 2_656 O3 C16 3.278(4) no . 1_655 O4 O2 3.163(3) no . 2_657 O4 O4 3.087(3) no . 2_657 O4 C3 3.194(4) no . 2_657 N1 C21 3.577(5) no . 2_656 C3 O4 3.194(4) no . 2_657 C5 O2 3.316(4) no . 2_657 C13 C13 3.494(5) no . 2_766 C16 O3 3.278(4) no . 1_455 C20 O2 3.528(4) no . 2_656 C21 N1 3.577(5) no . 2_656 O2 H16 2.2543 no . . O3 H5A 2.3896 no . . O3 H5B 3.5989 no . . O3 H7 3.4969 no . . O4 H11 2.7488 no . . N1 H18 2.5571 no . . C3 H5A 2.4636 no . . C3 H5B 3.1533 no . . C3 H16 3.5933 no . . C5 H7 2.6790 no . . C5 H11 2.6422 no . . C6 H8 3.2587 no . . C6 H10 3.2565 no . . C7 H5A 2.5754 no . . C7 H5B 3.0930 no . . C7 H11 3.2283 no . . C8 H10 3.2276 no . . C8 H13B 3.1557 no . . C8 H14A 2.6946 no . . C8 H14B 2.9880 no . . C9 H7 3.2784 no . . C9 H11 3.2783 no . . C9 H13A 2.6408 no . . C9 H13B 2.6451 no . . C9 H13C 3.3213 no . . C9 H14A 2.7232 no . . C9 H14B 2.7253 no . . C9 H14C 3.3711 no . . C9 H15A 2.7359 no . . C9 H15B 2.7327 no . . C9 H15C 3.3778 no . . C10 H8 3.2289 no . . C10 H13A 2.9467 no . . C10 H13B 3.5382 no . . C10 H15A 3.0865 no . . C10 H15B 2.6786 no . . C11 H5A 3.2992 no . . C11 H5B 2.7918 no . . C11 H7 3.2294 no . . C12 H8 2.7237 no . . C12 H10 2.6816 no . . C13 H8 3.4856 no . . C13 H10 3.2241 no . . C13 H14A 2.7010 no . . C13 H14B 3.3580 no . . C13 H14C 2.7062 no . . C13 H15A 3.3335 no . . C13 H15B 2.6501 no . . C13 H15C 2.6747 no . . C14 H8 2.5786 no . . C14 H13A 3.3582 no . . C14 H13B 2.7160 no . . C14 H13C 2.6904 no . . C14 H15A 2.6610 no . . C14 H15B 3.3216 no . . C14 H15C 2.6235 no . . C15 H10 2.6284 no . . C15 H13A 2.6710 no . . C15 H13B 3.3347 no . . C15 H13C 2.6508 no . . C15 H14A 3.3223 no . . C15 H14B 2.6621 no . . C15 H14C 2.6202 no . . C16 H18 2.6742 no . . C16 H22 2.6038 no . . C17 H19 3.2596 no . . C17 H21 3.2598 no . . C18 H16 3.3450 no . . C18 H20 3.2517 no . . C18 H22 3.2579 no . . C19 H21 3.2566 no . . C20 H18 3.2521 no . . C20 H22 3.2539 no . . C21 H19 3.2551 no . . C22 H16 2.6368 no . . C22 H18 3.2562 no . . C22 H20 3.2565 no . . H5A H7 2.3718 no . . H5A H11 3.5828 no . . H5B H7 3.2730 no . . H5B H11 2.7665 no . . H7 H8 2.3205 no . . H8 H13B 3.1435 no . . H8 H14A 2.0991 no . . H8 H14B 2.6599 no . . H8 H14C 3.5147 no . . H10 H11 2.3102 no . . H10 H13A 2.7751 no . . H10 H15A 2.8543 no . . H10 H15B 2.0804 no . . H10 H15C 3.5290 no . . H13A H14A 3.5991 no . . H13A H14C 3.5906 no . . H13A H15A 3.5594 no . . H13A H15B 2.4664 no . . H13A H15C 2.9746 no . . H13B H14A 2.5362 no . . H13B H14C 3.0122 no . . H13B H15B 3.5553 no . . H13B H15C 3.5645 no . . H13C H14A 2.9663 no . . H13C H14B 3.5862 no . . H13C H14C 2.5142 no . . H13C H15A 3.5558 no . . H13C H15B 2.9086 no . . H13C H15C 2.4712 no . . H14A H15A 3.5662 no . . H14A H15C 3.5178 no . . H14B H15A 2.4843 no . . H14B H15B 3.5654 no . . H14B H15C 2.9223 no . . H14C H15A 2.9160 no . . H14C H15B 3.5157 no . . H14C H15C 2.3992 no . . H16 H22 2.4325 no . . H18 H19 2.3168 no . . H19 H20 2.3414 no . . H20 H21 2.3342 no . . H21 H22 2.3315 no . . O2 H5A 3.3505 no . 2_657 O2 H5B 2.8980 no . 2_657 O2 H7 2.9089 no . 1_455 O2 H20 3.5127 no . 2_656 O3 H5A 3.2796 no . 2_757 O3 H15C 3.1219 no . 1_545 O3 H16 2.3868 no . 1_655 O3 H21 3.2768 no . 2_656 O3 H22 3.0795 no . 1_655 O4 H7 3.0459 no . 1_455 N1 H5B 3.0386 no . 2_657 N1 H15B 3.5104 no . 1_545 N1 H15C 3.1289 no . 1_545 N1 H22 3.2728 no . 1_655 C3 H7 3.5356 no . 1_455 C3 H16 3.5498 no . 1_655 C3 H20 3.4893 no . 2_656 C5 H5A 3.5966 no . 2_757 C5 H14B 3.3962 no . 2_767 C6 H14B 3.1030 no . 2_767 C6 H15A 3.2905 no . 2_767 C6 H20 3.5384 no . 2_656 C7 H11 3.3785 no . 1_655 C7 H15A 2.9365 no . 2_767 C7 H19 3.4250 no . 2_756 C8 H11 3.2082 no . 1_655 C8 H15A 3.5363 no . 2_767 C8 H19 2.9350 no . 2_756 C8 H20 3.4506 no . 2_756 C10 H8 3.3413 no . 1_455 C10 H10 3.4804 no . 2_667 C10 H11 3.2066 no . 2_667 C10 H14A 3.3515 no . 1_455 C10 H14B 3.4032 no . 1_455 C10 H20 3.2493 no . 2_656 C11 H8 3.1840 no . 1_455 C11 H10 3.1278 no . 2_667 C11 H14B 3.1305 no . 2_767 C11 H15B 3.5687 no . 2_667 C11 H20 3.1301 no . 2_656 C13 H13A 3.4665 no . 2_766 C13 H13B 2.9442 no . 2_766 C13 H13C 3.5289 no . 2_766 C13 H18 3.4528 no . 1_565 C14 H5B 3.4178 no . 2_767 C14 H10 2.9840 no . 1_655 C14 H13A 3.5649 no . 1_655 C14 H15B 3.2359 no . 1_655 C15 H11 3.2896 no . 2_667 C15 H18 3.5924 no . 1_565 C16 H5B 3.1736 no . 2_657 C16 H14C 3.3475 no . 1_445 C17 H14C 2.9042 no . 1_445 C18 H13C 3.4881 no . 1_545 C18 H14C 3.1305 no . 1_445 C18 H21 3.0944 no . 1_655 C18 H22 3.5699 no . 1_655 C19 H8 3.2629 no . 2_756 C19 H13B 3.5295 no . 2_756 C19 H21 3.1930 no . 1_655 C20 H8 3.2666 no . 2_756 C20 H13C 3.4158 no . 1_445 C21 H13C 2.9860 no . 1_445 C21 H18 3.0871 no . 1_455 C21 H19 3.5768 no . 1_455 C21 H22 3.1806 no . 2_556 C22 H13C 3.2580 no . 1_445 C22 H14C 3.2332 no . 1_445 C22 H15C 3.3408 no . 1_445 C22 H18 3.1844 no . 1_455 C22 H22 2.9898 no . 2_556 H5A O2 3.3505 no . 2_657 H5A O3 3.2796 no . 2_757 H5A C5 3.5966 no . 2_757 H5A H5A 2.6646 no . 2_757 H5A H15A 3.5094 no . 2_767 H5A H16 3.5844 no . 2_657 H5B O2 2.8980 no . 2_657 H5B N1 3.0386 no . 2_657 H5B C14 3.4178 no . 2_767 H5B C16 3.1736 no . 2_657 H5B H14B 2.7755 no . 2_767 H5B H14C 3.1791 no . 2_767 H5B H15A 3.5984 no . 2_667 H5B H15A 3.3566 no . 2_767 H5B H15B 2.9625 no . 2_667 H5B H16 3.1609 no . 2_657 H7 O2 2.9089 no . 1_655 H7 O4 3.0459 no . 1_655 H7 C3 3.5356 no . 1_655 H7 H11 3.0332 no . 1_655 H7 H15A 2.8222 no . 2_767 H7 H16 3.4027 no . 1_655 H7 H19 3.4769 no . 2_756 H7 H20 3.5650 no . 2_756 H8 C10 3.3413 no . 1_655 H8 C11 3.1840 no . 1_655 H8 C19 3.2629 no . 2_756 H8 C20 3.2666 no . 2_756 H8 H10 2.9741 no . 1_655 H8 H11 2.6892 no . 1_655 H8 H19 2.6392 no . 2_756 H8 H20 2.6508 no . 2_756 H10 C10 3.4804 no . 2_667 H10 C11 3.1278 no . 2_667 H10 C14 2.9840 no . 1_455 H10 H8 2.9741 no . 1_455 H10 H10 3.3633 no . 2_667 H10 H11 2.7103 no . 2_667 H10 H14A 2.6440 no . 1_455 H10 H14B 2.4871 no . 1_455 H10 H14C 3.4723 no . 1_455 H10 H20 3.4762 no . 2_656 H11 C7 3.3785 no . 1_455 H11 C8 3.2082 no . 1_455 H11 C10 3.2066 no . 2_667 H11 C15 3.2896 no . 2_667 H11 H7 3.0332 no . 1_455 H11 H8 2.6892 no . 1_455 H11 H10 2.7103 no . 2_667 H11 H14B 3.2629 no . 2_767 H11 H15A 2.7818 no . 2_667 H11 H15B 2.9082 no . 2_667 H11 H20 3.3078 no . 2_656 H13A C13 3.4665 no . 2_766 H13A C14 3.5649 no . 1_455 H13A H13B 2.7999 no . 2_766 H13A H13C 3.4093 no . 2_766 H13A H14A 2.9222 no . 1_455 H13A H14C 3.4923 no . 1_455 H13A H18 3.2843 no . 1_565 H13A H19 3.5870 no . 1_565 H13A H20 3.4741 no . 2_656 H13B C13 2.9442 no . 2_766 H13B C19 3.5295 no . 2_756 H13B H13A 2.7999 no . 2_766 H13B H13B 2.6555 no . 2_766 H13B H13C 2.8766 no . 2_766 H13B H19 2.7371 no . 2_756 H13C C13 3.5289 no . 2_766 H13C C18 3.4881 no . 1_565 H13C C20 3.4158 no . 1_665 H13C C21 2.9860 no . 1_665 H13C C22 3.2580 no . 1_665 H13C H13A 3.4093 no . 2_766 H13C H13B 2.8766 no . 2_766 H13C H18 2.7924 no . 1_565 H13C H19 3.3579 no . 1_565 H13C H21 3.0646 no . 1_665 H13C H22 3.4867 no . 1_665 H14A C10 3.3515 no . 1_655 H14A H10 2.6440 no . 1_655 H14A H13A 2.9222 no . 1_655 H14A H15B 3.2092 no . 1_655 H14A H19 3.3321 no . 2_756 H14A H20 3.3017 no . 2_756 H14B C5 3.3962 no . 2_767 H14B C6 3.1030 no . 2_767 H14B C10 3.4032 no . 1_655 H14B C11 3.1305 no . 2_767 H14B H5B 2.7755 no . 2_767 H14B H10 2.4871 no . 1_655 H14B H11 3.2629 no . 2_767 H14B H15B 2.8517 no . 1_655 H14C C16 3.3475 no . 1_665 H14C C17 2.9042 no . 1_665 H14C C18 3.1305 no . 1_665 H14C C22 3.2332 no . 1_665 H14C H5B 3.1791 no . 2_767 H14C H10 3.4723 no . 1_655 H14C H13A 3.4923 no . 1_655 H14C H15B 3.1097 no . 1_655 H14C H18 3.4533 no . 1_665 H15A C6 3.2905 no . 2_767 H15A C7 2.9365 no . 2_767 H15A C8 3.5363 no . 2_767 H15A H5A 3.5094 no . 2_767 H15A H5B 3.5984 no . 2_667 H15A H5B 3.3566 no . 2_767 H15A H7 2.8222 no . 2_767 H15A H11 2.7818 no . 2_667 H15B N1 3.5104 no . 1_565 H15B C11 3.5687 no . 2_667 H15B C14 3.2359 no . 1_455 H15B H5B 2.9625 no . 2_667 H15B H11 2.9082 no . 2_667 H15B H14A 3.2092 no . 1_455 H15B H14B 2.8517 no . 1_455 H15B H14C 3.1097 no . 1_455 H15B H18 3.3849 no . 1_565 H15C O3 3.1219 no . 1_565 H15C N1 3.1289 no . 1_565 H15C C22 3.3408 no . 1_665 H15C H18 3.0017 no . 1_565 H15C H22 3.0580 no . 1_665 H16 O3 2.3868 no . 1_455 H16 C3 3.5498 no . 1_455 H16 H5A 3.5844 no . 2_657 H16 H5B 3.1609 no . 2_657 H16 H7 3.4027 no . 1_455 H16 H21 3.2346 no . 2_556 H18 C13 3.4528 no . 1_545 H18 C15 3.5924 no . 1_545 H18 C21 3.0871 no . 1_655 H18 C22 3.1844 no . 1_655 H18 H13A 3.2843 no . 1_545 H18 H13C 2.7924 no . 1_545 H18 H14C 3.4533 no . 1_445 H18 H15B 3.3849 no . 1_545 H18 H15C 3.0017 no . 1_545 H18 H21 2.5525 no . 1_655 H18 H22 2.7363 no . 1_655 H19 C7 3.4250 no . 2_756 H19 C8 2.9350 no . 2_756 H19 C21 3.5768 no . 1_655 H19 H7 3.4769 no . 2_756 H19 H8 2.6392 no . 2_756 H19 H13A 3.5870 no . 1_545 H19 H13B 2.7371 no . 2_756 H19 H13C 3.3579 no . 1_545 H19 H14A 3.3321 no . 2_756 H19 H21 2.7529 no . 1_655 H20 O2 3.5127 no . 2_656 H20 C3 3.4893 no . 2_656 H20 C6 3.5384 no . 2_656 H20 C8 3.4506 no . 2_756 H20 C10 3.2493 no . 2_656 H20 C11 3.1301 no . 2_656 H20 H7 3.5650 no . 2_756 H20 H8 2.6508 no . 2_756 H20 H10 3.4762 no . 2_656 H20 H11 3.3078 no . 2_656 H20 H13A 3.4741 no . 2_656 H20 H14A 3.3017 no . 2_756 H21 O3 3.2768 no . 2_656 H21 C18 3.0944 no . 1_455 H21 C19 3.1930 no . 1_455 H21 H13C 3.0646 no . 1_445 H21 H16 3.2346 no . 2_556 H21 H18 2.5525 no . 1_455 H21 H19 2.7529 no . 1_455 H21 H22 2.9398 no . 2_556 H22 O3 3.0795 no . 1_455 H22 N1 3.2728 no . 1_455 H22 C18 3.5699 no . 1_455 H22 C21 3.1806 no . 2_556 H22 C22 2.9898 no . 2_556 H22 H13C 3.4867 no . 1_445 H22 H15C 3.0580 no . 1_445 H22 H18 2.7363 no . 1_455 H22 H21 2.9398 no . 2_556 H22 H22 2.5919 no . 2_556 data_14 _database_code_depnum_ccdc_archive 'CCDC 923532' #TrackingRef '17580_web_deposit_cif_file_1_RoyMcBurney_1360161219.6f.cif' _chemical_formula_sum 'C15 H12 F N O3' _chemical_formula_moiety 'C15 H12 F N O3' _chemical_formula_weight 273.26 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 1/2-X,1/2+Y,1/2-Z 3 -X,-Y,-Z 4 1/2+X,1/2-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 14.6982(17) _cell_length_b 4.5311(5) _cell_length_c 19.448(3) _cell_angle_alpha 90.0000 _cell_angle_beta 97.309(4) _cell_angle_gamma 90.0000 _cell_volume 1284.7(3) _cell_formula_units_Z 4 _cell_measurement_reflns_used 9159 _cell_measurement_theta_min 4.01 _cell_measurement_theta_max 67.56 _cell_measurement_temperature 173 #------------------------------------------------------------------------------ _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.240 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.020 _exptl_crystal_density_diffrn 1.413 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568.00 _exptl_absorpt_coefficient_mu 0.917 _exptl_absorpt_correction_type none #============================================================================== # 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 15766 _diffrn_reflns_av_R_equivalents 0.0465 _diffrn_measured_fraction_theta_max 0.960 _diffrn_reflns_theta_max 68.16 _diffrn_reflns_theta_full 67.00 _diffrn_measured_fraction_theta_full 0.973 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _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 2261 _reflns_number_gt 2011 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.1206 _refine_ls_wR_factor_ref 0.3223 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 2261 _refine_ls_number_parameters 181 _refine_ls_goodness_of_fit_ref 0.924 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.1764P)^2^+10.2369P] 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 0.780 _refine_diff_density_min -1.180 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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 F4 F 1.3070(2) 0.2880(7) 0.87100(15) 0.0379(8) Uani 1.0 4 d . . . O8 O 0.9300(3) 0.9460(9) 0.84100(18) 0.0379(9) Uani 1.0 4 d . . . O9 O 0.9090(3) 0.7280(9) 0.94300(18) 0.0379(9) Uani 1.0 4 d . . . O10 O 0.8200(3) 0.6370(9) 0.84000(18) 0.0379(9) Uani 1.0 4 d . . . N11 N 0.7690(3) 0.4300(11) 0.8790(3) 0.0379(11) Uani 1.0 4 d . . . C1 C 1.0930(4) 0.8740(13) 0.8740(3) 0.0379(13) Uani 1.0 4 d . . . C2 C 1.1280(4) 0.8080(13) 0.8130(3) 0.0379(13) Uani 1.0 4 d . . . C3 C 1.2000(4) 0.6080(13) 0.8120(3) 0.0379(13) Uani 1.0 4 d . . . C4 C 1.2360(4) 0.4850(13) 0.8720(3) 0.0379(13) Uani 1.0 4 d . . . C5 C 1.2060(4) 0.5380(13) 0.9340(3) 0.0379(13) Uani 1.0 4 d . . . C6 C 1.1330(4) 0.7380(13) 0.9340(3) 0.0379(13) Uani 1.0 4 d . . . C7 C 1.0150(4) 1.0840(13) 0.8750(3) 0.0379(13) Uani 1.0 4 d . . . C9 C 0.8890(4) 0.7670(12) 0.8830(3) 0.0379(13) Uani 1.0 4 d . . . C12 C 0.7030(4) 0.3420(13) 0.8370(3) 0.0379(13) Uani 1.0 4 d . . . C13 C 0.6370(4) 0.1310(13) 0.8630(3) 0.0379(13) Uani 1.0 4 d . . . C14 C 0.6500(4) 0.0220(13) 0.9300(3) 0.0379(13) Uani 1.0 4 d . . . C15 C 0.5820(4) -0.1670(13) 0.9530(3) 0.0379(13) Uani 1.0 4 d . . . C16 C 0.5060(4) -0.2440(12) 0.9060(3) 0.0379(13) Uani 1.0 4 d . . . C17 C 0.4950(4) -0.1360(13) 0.8400(3) 0.0379(13) Uani 1.0 4 d . . . C18 C 0.5610(4) 0.0480(13) 0.8170(3) 0.0379(13) Uani 1.0 4 d . . . H2 H 1.1025 0.9005 0.7711 0.0455 Uiso 1.0 4 calc R . . H3 H 1.2229 0.5603 0.7699 0.0455 Uiso 1.0 4 calc R . . H5 H 1.2330 0.4445 0.9753 0.0455 Uiso 1.0 4 calc R . . H6 H 1.1104 0.7812 0.9765 0.0455 Uiso 1.0 4 calc R . . H7A H 1.0077 1.1355 0.9235 0.0455 Uiso 1.0 4 calc R . . H7B H 1.0276 1.2677 0.8503 0.0455 Uiso 1.0 4 calc R . . H12 H 0.6951 0.4070 0.7902 0.0455 Uiso 1.0 4 calc R . . H14 H 0.7035 0.0722 0.9604 0.0455 Uiso 1.0 4 calc R . . H15 H 0.5885 -0.2385 0.9993 0.0455 Uiso 1.0 4 calc R . . H16 H 0.4612 -0.3738 0.9202 0.0455 Uiso 1.0 4 calc R . . H17 H 0.4417 -0.1867 0.8093 0.0455 Uiso 1.0 4 calc R . . H18 H 0.5541 0.1159 0.7704 0.0455 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 F4 0.0375(16) 0.0375(16) 0.0375(16) 0.0000(13) 0.0000(13) 0.0000(13) O8 0.038(2) 0.038(2) 0.0375(19) 0.0000(16) 0.0000(16) 0.0000(16) O9 0.038(2) 0.038(2) 0.038(2) 0.0000(16) 0.0000(16) 0.0000(16) O10 0.038(2) 0.038(2) 0.0375(19) 0.0000(16) 0.0000(15) 0.0000(16) N11 0.038(3) 0.038(3) 0.038(3) 0.000(2) 0.0000(19) 0.000(2) C1 0.038(3) 0.038(3) 0.038(3) 0.000(3) 0.000(3) 0.000(3) C2 0.038(3) 0.038(3) 0.038(3) 0.000(3) 0.000(3) 0.000(3) C3 0.038(3) 0.038(3) 0.038(3) 0.000(3) 0.000(3) 0.000(3) C4 0.038(3) 0.038(3) 0.038(3) 0.000(3) 0.000(3) 0.000(3) C5 0.038(3) 0.038(3) 0.038(3) 0.000(3) 0.000(3) 0.000(3) C6 0.038(3) 0.038(3) 0.038(3) 0.000(3) 0.000(3) 0.000(3) C7 0.038(3) 0.038(3) 0.038(3) 0.000(3) 0.000(3) 0.000(3) C9 0.038(3) 0.038(3) 0.038(3) 0.000(3) 0.000(3) 0.000(3) C12 0.038(3) 0.038(3) 0.038(3) 0.000(3) 0.000(3) 0.000(3) C13 0.038(3) 0.038(3) 0.038(3) 0.000(3) 0.000(3) 0.000(3) C14 0.038(3) 0.038(3) 0.038(3) 0.000(3) 0.000(3) 0.000(3) C15 0.038(3) 0.038(3) 0.038(3) 0.000(3) 0.000(3) 0.000(3) C16 0.038(3) 0.038(3) 0.038(3) 0.000(3) 0.000(3) 0.000(3) C17 0.038(3) 0.038(3) 0.038(3) 0.000(3) 0.000(3) 0.000(3) C18 0.038(3) 0.038(3) 0.038(3) 0.000(3) 0.000(3) 0.000(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 F4 C4 1.375(7) yes . . O8 C7 1.476(7) yes . . O8 C9 1.347(7) yes . . O9 C9 1.180(7) yes . . O10 N11 1.470(6) yes . . O10 C9 1.363(7) yes . . N11 C12 1.251(7) yes . . C1 C2 1.384(8) yes . . C1 C6 1.383(8) yes . . C1 C7 1.492(8) yes . . C2 C3 1.395(8) yes . . C3 C4 1.340(8) yes . . C4 C5 1.357(8) yes . . C5 C6 1.404(8) yes . . C12 C13 1.495(8) yes . . C13 C14 1.384(8) yes . . C13 C18 1.391(8) yes . . C14 C15 1.430(8) yes . . C15 C16 1.395(8) yes . . C16 C17 1.364(8) yes . . C17 C18 1.395(8) yes . . C2 H2 0.950 no . . C3 H3 0.950 no . . C5 H5 0.950 no . . C6 H6 0.950 no . . C7 H7A 0.990 no . . C7 H7B 0.990 no . . C12 H12 0.950 no . . C14 H14 0.950 no . . C15 H15 0.950 no . . C16 H16 0.950 no . . C17 H17 0.950 no . . C18 H18 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 C7 O8 C9 113.7(4) yes . . . N11 O10 C9 110.3(4) yes . . . O10 N11 C12 105.7(4) yes . . . C2 C1 C6 117.5(5) yes . . . C2 C1 C7 121.3(5) yes . . . C6 C1 C7 121.2(5) yes . . . C1 C2 C3 121.2(5) yes . . . C2 C3 C4 118.3(6) yes . . . F4 C4 C3 118.3(5) yes . . . F4 C4 C5 117.4(5) yes . . . C3 C4 C5 124.3(6) yes . . . C4 C5 C6 116.7(5) yes . . . C1 C6 C5 122.0(6) yes . . . O8 C7 C1 109.4(5) yes . . . O8 C9 O9 128.0(5) yes . . . O8 C9 O10 104.1(5) yes . . . O9 C9 O10 127.9(6) yes . . . N11 C12 C13 117.7(5) yes . . . C12 C13 C14 121.9(5) yes . . . C12 C13 C18 117.2(5) yes . . . C14 C13 C18 120.8(6) yes . . . C13 C14 C15 119.3(5) yes . . . C14 C15 C16 118.6(5) yes . . . C15 C16 C17 121.1(6) yes . . . C16 C17 C18 120.8(5) yes . . . C13 C18 C17 119.3(5) yes . . . C1 C2 H2 119.421 no . . . C3 C2 H2 119.421 no . . . C2 C3 H3 120.845 no . . . C4 C3 H3 120.845 no . . . C4 C5 H5 121.662 no . . . C6 C5 H5 121.670 no . . . C1 C6 H6 118.986 no . . . C5 C6 H6 118.988 no . . . O8 C7 H7A 109.798 no . . . O8 C7 H7B 109.795 no . . . C1 C7 H7A 109.797 no . . . C1 C7 H7B 109.800 no . . . H7A C7 H7B 108.246 no . . . N11 C12 H12 121.132 no . . . C13 C12 H12 121.127 no . . . C13 C14 H14 120.333 no . . . C15 C14 H14 120.336 no . . . C14 C15 H15 120.718 no . . . C16 C15 H15 120.724 no . . . C15 C16 H16 119.461 no . . . C17 C16 H16 119.464 no . . . C16 C17 H17 119.596 no . . . C18 C17 H17 119.601 no . . . C13 C18 H18 120.346 no . . . C17 C18 H18 120.343 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 C7 O8 C9 O9 6.2(8) no . . . . C7 O8 C9 O10 -172.8(4) no . . . . C9 O8 C7 C1 83.0(5) no . . . . N11 O10 C9 O8 179.4(4) no . . . . N11 O10 C9 O9 0.5(8) no . . . . C9 O10 N11 C12 174.4(4) no . . . . O10 N11 C12 C13 -178.6(4) no . . . . C2 C1 C6 C5 -0.5(8) no . . . . C6 C1 C2 C3 1.0(8) no . . . . C2 C1 C7 O8 71.0(7) no . . . . C7 C1 C2 C3 -179.0(5) no . . . . C6 C1 C7 O8 -108.9(6) no . . . . C7 C1 C6 C5 179.5(5) no . . . . C1 C2 C3 C4 -1.4(8) no . . . . C2 C3 C4 F4 -180.0(5) no . . . . C2 C3 C4 C5 1.2(9) no . . . . F4 C4 C5 C6 -179.5(4) no . . . . C3 C4 C5 C6 -0.7(8) no . . . . C4 C5 C6 C1 0.3(8) no . . . . N11 C12 C13 C14 -3.4(8) no . . . . N11 C12 C13 C18 176.4(5) no . . . . C12 C13 C14 C15 176.7(5) no . . . . C12 C13 C18 C17 -176.6(5) no . . . . C14 C13 C18 C17 3.2(8) no . . . . C18 C13 C14 C15 -3.0(8) no . . . . C13 C14 C15 C16 2.3(8) no . . . . C14 C15 C16 C17 -1.8(8) no . . . . C15 C16 C17 C18 1.9(9) no . . . . C16 C17 C18 C13 -2.6(8) 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 O8 N11 3.472(6) no . . O8 C2 3.092(7) no . . O8 C6 3.419(6) no . . O9 N11 2.637(6) no . . O9 C1 3.237(7) no . . O9 C6 3.320(7) no . . O9 C7 2.702(7) no . . O10 C7 3.505(7) no . . N11 C14 2.811(8) no . . N11 C18 3.586(7) no . . C1 C4 2.747(8) no . . C1 C9 3.064(8) no . . C2 C5 2.768(8) no . . C3 C6 2.746(8) no . . C6 C9 3.600(8) no . . C9 C12 3.371(8) no . . C13 C16 2.776(8) no . . C14 C17 2.784(8) no . . C15 C18 2.799(8) no . . F4 C2 3.488(6) no . 1_545 F4 C3 3.581(7) no . 1_545 F4 C17 3.481(7) no . 1_655 O8 O10 3.523(6) no . 1_565 O8 N11 3.376(6) no . 1_565 O8 C18 3.580(7) no . 2_656 O9 C5 3.326(7) no . 3_767 O9 C6 3.307(7) no . 3_767 O9 C6 3.512(7) no . 3_777 O10 O8 3.523(6) no . 1_545 O10 C12 3.540(7) no . 2_656 O10 C13 3.571(7) no . 1_565 N11 O8 3.376(6) no . 1_545 N11 C9 3.479(8) no . 1_545 N11 C14 3.418(8) no . 1_565 C1 C4 3.479(8) no . 1_565 C1 C5 3.561(8) no . 1_565 C2 F4 3.488(6) no . 1_565 C2 C4 3.575(8) no . 1_565 C3 F4 3.581(7) no . 1_565 C4 C1 3.479(8) no . 1_545 C4 C2 3.575(8) no . 1_545 C5 O9 3.326(7) no . 3_767 C5 C1 3.561(8) no . 1_545 C5 C7 3.551(8) no . 1_545 C6 O9 3.307(7) no . 3_767 C6 O9 3.512(7) no . 3_777 C6 C7 3.550(8) no . 1_545 C7 C5 3.551(8) no . 1_565 C7 C6 3.550(8) no . 1_565 C9 N11 3.479(8) no . 1_565 C12 O10 3.540(7) no . 2_646 C13 O10 3.571(7) no . 1_545 C13 C16 3.583(8) no . 1_565 C14 N11 3.418(8) no . 1_545 C15 C15 3.545(8) no . 3_657 C16 C13 3.583(8) no . 1_545 C17 F4 3.481(7) no . 1_455 C18 O8 3.580(7) no . 2_646 F4 H3 2.5101 no . . F4 H5 2.5227 no . . O8 H2 3.0332 no . . O8 H6 3.5718 no . . O9 H6 2.9589 no . . O9 H7A 2.4081 no . . O10 H12 2.2232 no . . N11 H14 2.5394 no . . C1 H3 3.2793 no . . C1 H5 3.2978 no . . C2 H6 3.2257 no . . C2 H7A 3.3028 no . . C2 H7B 2.7050 no . . C3 H5 3.2378 no . . C4 H2 3.2037 no . . C4 H6 3.2089 no . . C5 H3 3.2350 no . . C6 H2 3.2279 no . . C6 H7A 2.5649 no . . C6 H7B 3.1888 no . . C7 H2 2.6632 no . . C7 H6 2.6539 no . . C9 H6 3.5208 no . . C9 H7A 2.4705 no . . C9 H7B 3.1670 no . . C9 H12 3.5683 no . . C12 H14 2.6926 no . . C12 H18 2.6067 no . . C13 H15 3.2890 no . . C13 H17 3.2612 no . . C14 H12 3.3668 no . . C14 H16 3.2897 no . . C14 H18 3.2691 no . . C15 H17 3.2557 no . . C16 H14 3.2895 no . . C16 H18 3.2538 no . . C17 H15 3.2582 no . . C18 H12 2.6579 no . . C18 H14 3.2701 no . . C18 H16 3.2531 no . . H2 H3 2.3491 no . . H2 H7A 3.5930 no . . H2 H7B 2.6056 no . . H5 H6 2.3638 no . . H6 H7A 2.3498 no . . H6 H7B 3.4068 no . . H12 H18 2.4452 no . . H14 H15 2.3957 no . . H15 H16 2.3475 no . . H16 H17 2.3006 no . . H17 H18 2.3447 no . . F4 H2 3.2555 no . 2_746 F4 H3 2.9078 no . 2_746 F4 H15 2.7909 no . 3_757 F4 H16 2.8011 no . 1_665 F4 H17 3.2546 no . 1_655 F4 H17 3.4105 no . 1_665 O8 H7B 3.3866 no . 1_545 O8 H12 2.9541 no . 2_656 O8 H18 2.6674 no . 2_656 O9 H5 2.8870 no . 3_767 O9 H6 2.8226 no . 3_767 O9 H6 2.7550 no . 3_777 O9 H7A 3.0983 no . 1_545 O9 H7A 2.7955 no . 3_777 O9 H7B 3.3816 no . 1_545 O9 H14 3.4535 no . 1_565 O10 H7B 3.4631 no . 1_545 O10 H12 2.7952 no . 2_656 O10 H18 3.0091 no . 2_656 N11 H5 2.8932 no . 3_767 N11 H6 3.2687 no . 3_767 N11 H14 3.5053 no . 1_565 C1 H7B 2.9276 no . 1_545 C1 H18 3.5193 no . 2_656 C2 H3 3.0989 no . 2_756 C2 H7B 2.9952 no . 1_545 C2 H17 3.3337 no . 2_656 C2 H17 3.3663 no . 2_666 C2 H18 3.0739 no . 2_656 C3 H2 3.5597 no . 1_545 C3 H3 3.2306 no . 2_746 C3 H3 2.9113 no . 2_756 C3 H7B 3.1362 no . 1_545 C3 H17 3.2311 no . 2_656 C4 H3 3.4789 no . 2_746 C4 H7B 3.1942 no . 1_545 C4 H15 3.5393 no . 3_757 C4 H16 3.3839 no . 1_665 C5 H7A 3.4218 no . 1_545 C5 H7B 3.1527 no . 1_545 C5 H14 3.5964 no . 3_757 C5 H14 2.9000 no . 3_767 C5 H15 3.4137 no . 3_757 C6 H5 3.5714 no . 1_565 C6 H7A 3.2848 no . 1_545 C6 H7B 2.9914 no . 1_545 C6 H14 3.0779 no . 3_767 C7 H18 3.5773 no . 2_656 C9 H6 3.4129 no . 3_777 C9 H7A 3.3919 no . 1_545 C9 H7B 3.1623 no . 1_545 C9 H12 3.4949 no . 2_656 C9 H14 3.5572 no . 1_565 C9 H18 3.2717 no . 2_656 C14 H5 3.1634 no . 3_757 C14 H5 3.3739 no . 3_767 C15 H5 3.1544 no . 3_757 C15 H15 3.3327 no . 3_657 C15 H16 3.3484 no . 3_647 C15 H16 3.5898 no . 3_657 C16 H15 3.3868 no . 3_647 C16 H15 3.2791 no . 3_657 C17 H2 3.2165 no . 2_636 C17 H2 3.4416 no . 2_646 C18 H2 3.1964 no . 2_646 C18 H7B 3.5803 no . 2_636 C18 H12 3.5851 no . 1_545 H2 F4 3.2555 no . 2_756 H2 C3 3.5597 no . 1_565 H2 C17 3.4416 no . 2_656 H2 C17 3.2165 no . 2_666 H2 C18 3.1964 no . 2_656 H2 H3 3.4752 no . 1_565 H2 H3 2.8738 no . 2_756 H2 H7B 3.4988 no . 1_545 H2 H17 3.1128 no . 2_656 H2 H17 2.4717 no . 2_666 H2 H18 2.6728 no . 2_656 H3 F4 2.9078 no . 2_756 H3 C2 3.0989 no . 2_746 H3 C3 2.9113 no . 2_746 H3 C3 3.2306 no . 2_756 H3 C4 3.4789 no . 2_756 H3 H2 3.4752 no . 1_545 H3 H2 2.8738 no . 2_746 H3 H3 2.5533 no . 2_746 H3 H3 2.5533 no . 2_756 H3 H17 3.4091 no . 1_665 H3 H17 2.9209 no . 2_656 H5 O9 2.8870 no . 3_767 H5 N11 2.8932 no . 3_767 H5 C6 3.5714 no . 1_545 H5 C14 3.1634 no . 3_757 H5 C14 3.3739 no . 3_767 H5 C15 3.1544 no . 3_757 H5 H6 3.5061 no . 1_545 H5 H14 2.7595 no . 3_757 H5 H14 2.6325 no . 3_767 H5 H15 2.7692 no . 3_757 H6 O9 2.8226 no . 3_767 H6 O9 2.7550 no . 3_777 H6 N11 3.2687 no . 3_767 H6 C9 3.4129 no . 3_777 H6 H5 3.5061 no . 1_565 H6 H7A 3.3921 no . 1_545 H6 H7A 2.7926 no . 3_777 H6 H7B 3.4870 no . 1_545 H6 H14 2.9276 no . 3_767 H7A O9 3.0983 no . 1_565 H7A O9 2.7955 no . 3_777 H7A C5 3.4218 no . 1_565 H7A C6 3.2848 no . 1_565 H7A C9 3.3919 no . 1_565 H7A H6 3.3921 no . 1_565 H7A H6 2.7926 no . 3_777 H7A H7A 3.2541 no . 3_777 H7B O8 3.3866 no . 1_565 H7B O9 3.3816 no . 1_565 H7B O10 3.4631 no . 1_565 H7B C1 2.9276 no . 1_565 H7B C2 2.9952 no . 1_565 H7B C3 3.1362 no . 1_565 H7B C4 3.1942 no . 1_565 H7B C5 3.1527 no . 1_565 H7B C6 2.9914 no . 1_565 H7B C9 3.1623 no . 1_565 H7B C18 3.5803 no . 2_666 H7B H2 3.4988 no . 1_565 H7B H6 3.4870 no . 1_565 H7B H17 3.2001 no . 2_666 H7B H18 2.9540 no . 2_666 H12 O8 2.9541 no . 2_646 H12 O10 2.7952 no . 2_646 H12 C9 3.4949 no . 2_646 H12 C18 3.5851 no . 1_565 H12 H12 3.2898 no . 2_646 H12 H12 3.2898 no . 2_656 H14 O9 3.4535 no . 1_545 H14 N11 3.5053 no . 1_545 H14 C5 3.5964 no . 3_757 H14 C5 2.9000 no . 3_767 H14 C6 3.0779 no . 3_767 H14 C9 3.5572 no . 1_545 H14 H5 2.7595 no . 3_757 H14 H5 2.6325 no . 3_767 H14 H6 2.9276 no . 3_767 H15 F4 2.7909 no . 3_757 H15 C4 3.5393 no . 3_757 H15 C5 3.4137 no . 3_757 H15 C15 3.3327 no . 3_657 H15 C16 3.3868 no . 3_647 H15 C16 3.2791 no . 3_657 H15 H5 2.7692 no . 3_757 H15 H15 3.5211 no . 3_647 H15 H15 3.3845 no . 3_657 H15 H16 2.5222 no . 3_647 H15 H16 3.3126 no . 3_657 H16 F4 2.8011 no . 1_445 H16 C4 3.3839 no . 1_445 H16 C15 3.3484 no . 3_647 H16 C15 3.5898 no . 3_657 H16 H15 2.5222 no . 3_647 H16 H15 3.3126 no . 3_657 H16 H16 3.3684 no . 3_647 H17 F4 3.4105 no . 1_445 H17 F4 3.2546 no . 1_455 H17 C2 3.3663 no . 2_636 H17 C2 3.3337 no . 2_646 H17 C3 3.2311 no . 2_646 H17 H2 2.4717 no . 2_636 H17 H2 3.1128 no . 2_646 H17 H3 3.4091 no . 1_445 H17 H3 2.9209 no . 2_646 H17 H7B 3.2001 no . 2_636 H18 O8 2.6674 no . 2_646 H18 O10 3.0091 no . 2_646 H18 C1 3.5193 no . 2_646 H18 C2 3.0739 no . 2_646 H18 C7 3.5773 no . 2_646 H18 C9 3.2717 no . 2_646 H18 H2 2.6728 no . 2_646 H18 H7B 2.9540 no . 2_636 data_13 _database_code_depnum_ccdc_archive 'CCDC 923533' #TrackingRef '17626_web_deposit_cif_file_0_RoyMcBurney_1360313178.6g.cif' _chemical_formula_sum 'C17 H17 N O6 S' _chemical_formula_moiety 'C17 H17 N O6 S' _chemical_formula_weight 363.38 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,-Y,-Z #------------------------------------------------------------------------------ _cell_length_a 5.707(7) _cell_length_b 7.877(11) _cell_length_c 18.99(3) _cell_angle_alpha 98.61(6) _cell_angle_beta 91.40(8) _cell_angle_gamma 91.03(3) _cell_volume 843(2) _cell_formula_units_Z 2 _cell_measurement_reflns_used 821 _cell_measurement_theta_min 21.09 _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 0.010 _exptl_crystal_density_diffrn 1.431 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 380.00 _exptl_absorpt_coefficient_mu 2.019 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'REQAB (Rigaku, 1998)' _exptl_absorpt_correction_T_min 0.371 _exptl_absorpt_correction_T_max 0.980 #============================================================================== # 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 11643 _diffrn_reflns_av_R_equivalents 0.1733 _diffrn_reflns_theta_max 68.27 _diffrn_measured_fraction_theta_max 0.941 _diffrn_reflns_theta_full 67.00 _diffrn_measured_fraction_theta_full 0.949 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -22 _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 2905 _reflns_number_gt 1673 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.1261 _refine_ls_wR_factor_ref 0.4028 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 2905 _refine_ls_number_parameters 227 _refine_ls_goodness_of_fit_ref 1.233 _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 0.034 _refine_diff_density_max 0.560 _refine_diff_density_min -0.410 _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.046(9) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 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) ; S S 0.3331 0.5567 ; 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 S1 S 0.5715(3) 1.2377(3) 0.95644(8) 0.0957(9) Uani 1.0 2 d . . . O4 O 0.6140(7) 1.0717(6) 0.90009(18) 0.0921(14) Uani 1.0 2 d . . . O8 O 0.2478(9) 0.8649(6) 0.5804(3) 0.1080(17) Uani 1.0 2 d . . . O9 O 0.2348(10) 0.9603(8) 0.4741(3) 0.125(2) Uani 1.0 2 d . . . O10 O 0.1942(9) 0.6806(7) 0.4873(3) 0.1130(18) Uani 1.0 2 d . . . O19 O 0.6287(9) 1.3863(7) 0.9261(3) 0.1095(16) Uani 1.0 2 d . . . O20 O 0.6963(9) 1.2044(7) 1.0184(2) 0.1141(17) Uani 1.0 2 d . . . N11 N 0.1223(11) 0.6528(8) 0.4135(3) 0.112(2) Uani 1.0 2 d . . . C1 C 0.3711(13) 1.0376(9) 0.6896(4) 0.0913(19) Uani 1.0 2 d . . . C2 C 0.2434(12) 0.9650(10) 0.7389(4) 0.102(2) Uani 1.0 2 d . . . C3 C 0.3276(12) 0.9761(9) 0.8102(4) 0.0937(19) Uani 1.0 2 d . . . C4 C 0.5314(12) 1.0667(9) 0.8294(4) 0.0866(18) Uani 1.0 2 d . . . C5 C 0.6644(12) 1.1394(9) 0.7828(3) 0.093(2) Uani 1.0 2 d . . . C6 C 0.5807(12) 1.1227(9) 0.7117(4) 0.096(2) Uani 1.0 2 d . . . C7 C 0.2782(14) 1.0375(10) 0.6154(4) 0.115(3) Uani 1.0 2 d . . . C9 C 0.2249(16) 0.8509(13) 0.5114(5) 0.121(3) Uani 1.0 2 d . . . C12 C 0.1698(12) 0.5002(9) 0.3834(4) 0.097(2) Uani 1.0 2 d . . . C13 C 0.0967(12) 0.4685(9) 0.3072(3) 0.094(2) Uani 1.0 2 d . . . C14 C -0.1130(13) 0.5316(9) 0.2828(4) 0.099(2) Uani 1.0 2 d . . . C15 C -0.1770(12) 0.5090(9) 0.2121(4) 0.097(2) Uani 1.0 2 d . . . C16 C -0.0337(13) 0.4193(10) 0.1623(4) 0.099(2) Uani 1.0 2 d . . . C17 C 0.1697(13) 0.3502(10) 0.1856(4) 0.106(3) Uani 1.0 2 d . . . C18 C 0.2360(13) 0.3727(9) 0.2571(4) 0.0960(19) Uani 1.0 2 d . . . C19 C 0.2979(15) 0.3719(10) 0.4177(4) 0.121(3) Uani 1.0 2 d . . . C20 C 0.2689(12) 1.2311(10) 0.9706(4) 0.104(3) Uani 1.0 2 d . . . H2 H 0.0982 0.9075 0.7249 0.1219 Uiso 1.0 2 calc R . . H3 H 0.2447 0.9220 0.8438 0.1124 Uiso 1.0 2 calc R . . H5 H 0.8076 1.1989 0.7976 0.1117 Uiso 1.0 2 calc R . . H6 H 0.6705 1.1712 0.6779 0.1153 Uiso 1.0 2 calc R . . H7A H 0.1262 1.0963 0.6166 0.1383 Uiso 1.0 2 calc R . . H7B H 0.3891 1.1005 0.5888 0.1383 Uiso 1.0 2 calc R . . H14 H -0.2140 0.5921 0.3164 0.1184 Uiso 1.0 2 calc R . . H15 H -0.3195 0.5547 0.1971 0.1162 Uiso 1.0 2 calc R . . H16 H -0.0745 0.4055 0.1129 0.1194 Uiso 1.0 2 calc R . . H17 H 0.2663 0.2858 0.1519 0.1276 Uiso 1.0 2 calc R . . H18 H 0.3758 0.3231 0.2721 0.1152 Uiso 1.0 2 calc R . . H19A H 0.2150 0.3492 0.4600 0.1446 Uiso 1.0 2 calc R . . H19B H 0.4565 0.4161 0.4317 0.1446 Uiso 1.0 2 calc R . . H19C H 0.3074 0.2651 0.3840 0.1446 Uiso 1.0 2 calc R . . H20A H 0.2313 1.3187 1.0108 0.1247 Uiso 1.0 2 calc R . . H20B H 0.2230 1.1174 0.9813 0.1247 Uiso 1.0 2 calc R . . H20C H 0.1835 1.2536 0.9277 0.1247 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 S1 0.1075(15) 0.1005(15) 0.0731(12) 0.0032(11) -0.0025(9) -0.0062(9) O4 0.103(3) 0.101(4) 0.066(3) 0.017(3) -0.005(2) -0.010(2) O8 0.129(4) 0.111(4) 0.074(3) 0.031(3) -0.022(3) -0.018(3) O9 0.148(5) 0.126(5) 0.091(4) 0.025(4) -0.025(4) -0.011(3) O10 0.136(4) 0.117(4) 0.077(3) 0.027(3) -0.020(3) -0.018(3) O19 0.139(4) 0.102(4) 0.081(3) -0.008(3) 0.014(3) -0.011(3) O20 0.130(4) 0.133(4) 0.072(3) 0.009(3) -0.021(3) -0.006(3) N11 0.139(5) 0.122(5) 0.069(3) 0.038(4) -0.014(3) -0.012(3) C1 0.096(5) 0.095(5) 0.077(4) 0.022(4) -0.005(4) -0.009(4) C2 0.089(5) 0.108(6) 0.098(5) 0.013(4) 0.003(4) -0.016(4) C3 0.094(5) 0.102(5) 0.079(4) 0.007(4) 0.006(4) -0.007(4) C4 0.091(4) 0.093(5) 0.071(4) 0.013(4) -0.005(3) -0.007(3) C5 0.094(5) 0.107(5) 0.071(4) 0.018(4) -0.009(4) -0.009(4) C6 0.092(5) 0.110(5) 0.082(4) 0.012(4) -0.002(4) 0.001(4) C7 0.125(6) 0.119(6) 0.088(5) 0.042(5) -0.034(4) -0.028(4) C9 0.143(7) 0.131(7) 0.079(5) 0.055(6) -0.016(5) -0.018(5) C12 0.095(5) 0.104(5) 0.083(4) 0.020(4) -0.000(4) -0.014(4) C13 0.105(5) 0.098(5) 0.071(4) 0.015(4) -0.011(3) -0.010(3) C14 0.100(5) 0.099(5) 0.090(5) 0.025(4) -0.003(4) -0.010(4) C15 0.095(5) 0.111(5) 0.080(4) 0.013(4) -0.012(4) 0.000(4) C16 0.106(5) 0.105(5) 0.084(4) 0.005(4) -0.005(4) 0.003(4) C17 0.120(6) 0.118(6) 0.075(4) 0.011(5) 0.001(4) -0.007(4) C18 0.102(5) 0.099(5) 0.081(4) 0.010(4) -0.004(4) -0.004(4) C19 0.143(7) 0.130(6) 0.083(5) 0.043(6) -0.016(4) -0.004(4) C20 0.104(5) 0.117(6) 0.085(4) 0.017(4) 0.009(4) -0.005(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 S1 O4 1.587(5) yes . . S1 O19 1.416(6) yes . . S1 O20 1.420(5) yes . . S1 C20 1.755(8) yes . . O4 C4 1.407(8) yes . . O8 C7 1.426(9) yes . . O8 C9 1.302(10) yes . . O9 C9 1.196(12) yes . . O10 N11 1.433(7) yes . . O10 C9 1.357(11) yes . . N11 C12 1.288(9) yes . . C1 C2 1.384(11) yes . . C1 C6 1.385(10) yes . . C1 C7 1.492(10) yes . . C2 C3 1.415(10) yes . . C3 C4 1.366(10) yes . . C4 C5 1.362(10) yes . . C5 C6 1.406(9) yes . . C12 C13 1.480(9) yes . . C12 C19 1.476(11) yes . . C13 C14 1.399(10) yes . . C13 C18 1.396(9) yes . . C14 C15 1.368(10) yes . . C15 C16 1.385(10) yes . . C16 C17 1.382(11) yes . . C17 C18 1.385(9) yes . . C2 H2 0.950 no . . C3 H3 0.950 no . . C5 H5 0.950 no . . C6 H6 0.950 no . . C7 H7A 0.990 no . . C7 H7B 0.990 no . . C14 H14 0.950 no . . C15 H15 0.950 no . . C16 H16 0.950 no . . C17 H17 0.950 no . . C18 H18 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 O4 S1 O19 109.3(3) yes . . . O4 S1 O20 103.4(3) yes . . . O4 S1 C20 104.2(3) yes . . . O19 S1 O20 119.6(3) yes . . . O19 S1 C20 109.3(4) yes . . . O20 S1 C20 109.8(4) yes . . . S1 O4 C4 119.2(4) yes . . . C7 O8 C9 113.9(7) yes . . . N11 O10 C9 110.7(6) yes . . . O10 N11 C12 111.5(6) yes . . . C2 C1 C6 118.6(6) yes . . . C2 C1 C7 121.3(7) yes . . . C6 C1 C7 120.0(7) yes . . . C1 C2 C3 120.4(7) yes . . . C2 C3 C4 118.2(7) yes . . . O4 C4 C3 116.9(6) yes . . . O4 C4 C5 119.3(6) yes . . . C3 C4 C5 123.6(6) yes . . . C4 C5 C6 117.2(6) yes . . . C1 C6 C5 121.9(7) yes . . . O8 C7 C1 109.5(6) yes . . . O8 C9 O9 129.2(9) yes . . . O8 C9 O10 106.1(8) yes . . . O9 C9 O10 124.7(7) yes . . . N11 C12 C13 112.5(7) yes . . . N11 C12 C19 125.3(6) yes . . . C13 C12 C19 122.1(6) yes . . . C12 C13 C14 121.7(6) yes . . . C12 C13 C18 120.5(6) yes . . . C14 C13 C18 117.8(6) yes . . . C13 C14 C15 122.0(7) yes . . . C14 C15 C16 120.0(7) yes . . . C15 C16 C17 118.9(7) yes . . . C16 C17 C18 121.5(7) yes . . . C13 C18 C17 119.7(7) yes . . . C1 C2 H2 119.807 no . . . C3 C2 H2 119.781 no . . . C2 C3 H3 120.898 no . . . C4 C3 H3 120.890 no . . . C4 C5 H5 121.426 no . . . C6 C5 H5 121.400 no . . . C1 C6 H6 119.034 no . . . C5 C6 H6 119.032 no . . . O8 C7 H7A 109.763 no . . . O8 C7 H7B 109.761 no . . . C1 C7 H7A 109.772 no . . . C1 C7 H7B 109.762 no . . . H7A C7 H7B 108.223 no . . . C13 C14 H14 119.014 no . . . C15 C14 H14 119.005 no . . . C14 C15 H15 120.026 no . . . C16 C15 H15 120.024 no . . . C15 C16 H16 120.556 no . . . C17 C16 H16 120.550 no . . . C16 C17 H17 119.235 no . . . C18 C17 H17 119.232 no . . . C13 C18 H18 120.126 no . . . C17 C18 H18 120.127 no . . . C12 C19 H19A 109.474 no . . . C12 C19 H19B 109.470 no . . . C12 C19 H19C 109.469 no . . . H19A C19 H19B 109.474 no . . . H19A C19 H19C 109.470 no . . . H19B C19 H19C 109.470 no . . . S1 C20 H20A 109.469 no . . . S1 C20 H20B 109.473 no . . . S1 C20 H20C 109.474 no . . . H20A C20 H20B 109.469 no . . . H20A C20 H20C 109.467 no . . . H20B C20 H20C 109.476 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 O19 S1 O4 C4 -45.9(4) no . . . . O20 S1 O4 C4 -174.4(4) no . . . . C20 S1 O4 C4 70.8(4) no . . . . S1 O4 C4 C3 -101.0(6) no . . . . S1 O4 C4 C5 83.9(6) no . . . . C7 O8 C9 O9 3.1(12) no . . . . C7 O8 C9 O10 -179.0(6) no . . . . C9 O8 C7 C1 -163.6(6) no . . . . N11 O10 C9 O8 168.8(6) no . . . . N11 O10 C9 O9 -13.2(11) no . . . . C9 O10 N11 C12 157.5(6) no . . . . O10 N11 C12 C13 179.9(5) no . . . . O10 N11 C12 C19 -4.4(9) no . . . . C2 C1 C6 C5 -1.0(10) no . . . . C6 C1 C2 C3 -0.8(10) no . . . . C2 C1 C7 O8 -62.6(9) no . . . . C7 C1 C2 C3 -175.9(6) no . . . . C6 C1 C7 O8 122.4(7) no . . . . C7 C1 C6 C5 174.1(6) no . . . . C1 C2 C3 C4 3.0(10) no . . . . C2 C3 C4 O4 -178.4(6) no . . . . C2 C3 C4 C5 -3.5(10) no . . . . O4 C4 C5 C6 176.5(5) no . . . . C3 C4 C5 C6 1.8(10) no . . . . C4 C5 C6 C1 0.6(10) no . . . . N11 C12 C13 C14 -38.9(9) no . . . . N11 C12 C13 C18 141.5(6) no . . . . C19 C12 C13 C14 145.2(7) no . . . . C19 C12 C13 C18 -34.4(10) no . . . . C12 C13 C14 C15 177.2(6) no . . . . C12 C13 C18 C17 -177.4(6) no . . . . C14 C13 C18 C17 3.0(10) no . . . . C18 C13 C14 C15 -3.2(10) no . . . . C13 C14 C15 C16 0.8(11) no . . . . C14 C15 C16 C17 1.7(11) no . . . . C15 C16 C17 C18 -1.8(11) no . . . . C16 C17 C18 C13 -0.6(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 S1 C3 3.448(8) no . . S1 C5 3.330(8) no . . O8 N11 3.407(8) no . . O8 C2 2.995(10) no . . O8 C6 3.472(9) no . . O9 N11 2.583(9) no . . O9 C7 2.665(10) no . . O10 C7 3.449(9) no . . O10 C13 3.599(9) no . . O10 C19 2.672(10) no . . O19 C4 2.921(9) no . . O19 C5 3.111(8) no . . N11 C14 2.820(9) no . . N11 C18 3.506(9) no . . C1 C4 2.761(10) no . . C1 C9 3.554(11) no . . C2 C5 2.791(10) no . . C3 C6 2.763(11) no . . C3 C20 3.416(10) no . . C4 C20 3.216(10) no . . C9 C12 3.399(12) no . . C13 C16 2.800(10) no . . C14 C17 2.736(10) no . . C15 C18 2.776(11) no . . C18 C19 3.060(11) no . . O4 O20 3.357(8) no . 2_677 O8 O9 3.313(9) no . 2_576 O8 O9 3.481(9) no . 2_676 O8 C19 3.224(10) no . 2_666 O9 O8 3.313(9) no . 2_576 O9 O8 3.481(9) no . 2_676 O9 O9 2.923(9) no . 2_576 O9 O9 3.182(9) no . 2_676 O9 C7 3.350(10) no . 2_576 O9 C7 3.293(10) no . 2_676 O9 C9 3.037(12) no . 2_576 O9 C9 3.386(12) no . 2_676 O9 C19 3.579(12) no . 1_565 O10 C19 3.427(10) no . 2_566 O10 C19 3.441(10) no . 2_666 O19 O19 3.470(8) no . 2_687 O19 C16 3.366(10) no . 2_676 O19 C17 3.389(10) no . 2_676 O19 C20 3.374(9) no . 2_687 O20 O4 3.357(8) no . 2_677 O20 C16 3.320(9) no . 1_666 O20 C20 3.424(10) no . 1_655 O20 C20 3.477(11) no . 2_677 N11 C7 3.466(11) no . 2_576 C7 O9 3.350(10) no . 2_576 C7 O9 3.293(10) no . 2_676 C7 N11 3.466(11) no . 2_576 C9 O9 3.037(12) no . 2_576 C9 O9 3.386(12) no . 2_676 C9 C9 3.572(14) no . 2_576 C16 O19 3.366(10) no . 2_676 C16 O20 3.320(9) no . 1_444 C17 O19 3.389(10) no . 2_676 C19 O8 3.224(10) no . 2_666 C19 O9 3.579(12) no . 1_545 C19 O10 3.427(10) no . 2_566 C19 O10 3.441(10) no . 2_666 C20 O19 3.374(9) no . 2_687 C20 O20 3.424(10) no . 1_455 C20 O20 3.477(11) no . 2_677 S1 H3 3.5043 no . . S1 H5 3.3075 no . . O4 H3 2.5295 no . . O4 H5 2.5804 no . . O4 H20A 3.4824 no . . O4 H20B 2.7414 no . . O4 H20C 2.8857 no . . O8 H2 2.8651 no . . O9 H7A 2.8447 no . . O9 H7B 2.4269 no . . O10 H19A 2.5894 no . . O10 H19B 2.6883 no . . O19 H5 2.8749 no . . O19 H20A 2.8993 no . . O19 H20B 3.3985 no . . O19 H20C 2.7320 no . . O20 H20A 2.8245 no . . O20 H20B 2.8208 no . . O20 H20C 3.4163 no . . N11 H14 2.6157 no . . N11 H19A 2.7257 no . . N11 H19B 2.7424 no . . N11 H19C 3.2229 no . . C1 H3 3.2872 no . . C1 H5 3.2991 no . . C2 H6 3.2367 no . . C2 H7A 2.7527 no . . C2 H7B 3.3085 no . . C3 H5 3.2595 no . . C3 H20B 3.3439 no . . C3 H20C 3.0205 no . . C4 H2 3.2437 no . . C4 H6 3.2201 no . . C4 H20B 3.3918 no . . C4 H20C 3.0096 no . . C5 H3 3.2553 no . . C6 H2 3.2417 no . . C6 H7A 3.1099 no . . C6 H7B 2.5334 no . . C7 H2 2.6701 no . . C7 H6 2.6346 no . . C9 H7A 2.6429 no . . C9 H7B 2.4299 no . . C12 H14 2.6711 no . . C12 H18 2.6639 no . . C13 H15 3.2730 no . . C13 H17 3.2596 no . . C13 H19A 3.2397 no . . C13 H19B 3.1715 no . . C13 H19C 2.6119 no . . C14 H16 3.2438 no . . C14 H18 3.2576 no . . C15 H17 3.2395 no . . C16 H14 3.2369 no . . C16 H18 3.2674 no . . C17 H15 3.2439 no . . C18 H14 3.2506 no . . C18 H16 3.2705 no . . C18 H19B 3.4819 no . . C18 H19C 2.6947 no . . C19 H18 2.7809 no . . C20 H3 3.1559 no . . H2 H3 2.3747 no . . H2 H7A 2.7177 no . . H3 H20B 2.8309 no . . H3 H20C 2.8799 no . . H5 H6 2.3623 no . . H6 H7A 3.3023 no . . H6 H7B 2.3034 no . . H14 H15 2.3040 no . . H15 H16 2.3440 no . . H16 H17 2.3288 no . . H17 H18 2.3256 no . . H18 H19B 3.0311 no . . H18 H19C 2.2810 no . . S1 H20B 3.4114 no . 2_677 S1 H20C 3.5512 no . 1_655 O4 H17 2.9392 no . 2_666 O4 H20B 3.0182 no . 2_677 O4 H20C 3.5229 no . 1_655 O8 H19A 3.1243 no . 2_566 O8 H19A 3.5704 no . 2_666 O8 H19B 2.7932 no . 2_666 O8 H19C 3.4261 no . 2_566 O8 H19C 2.8575 no . 2_666 O9 H6 2.9825 no . 2_676 O9 H7A 2.6399 no . 2_576 O9 H7B 2.5003 no . 2_676 O9 H19A 3.1191 no . 1_565 O9 H19C 3.1768 no . 1_565 O10 H7A 3.3608 no . 2_576 O10 H7B 3.3882 no . 2_676 O10 H19A 2.5838 no . 2_566 O10 H19A 3.5154 no . 2_666 O10 H19B 2.6788 no . 2_666 O19 H15 2.9912 no . 2_576 O19 H16 3.1649 no . 2_676 O19 H17 3.2176 no . 2_676 O19 H20A 2.5549 no . 2_687 O19 H20C 3.3530 no . 1_655 O20 H3 2.9499 no . 2_677 O20 H16 2.5299 no . 1_666 O20 H17 3.5682 no . 1_566 O20 H20A 3.1801 no . 1_655 O20 H20B 3.1675 no . 1_655 O20 H20B 2.5853 no . 2_677 O20 H20C 3.3525 no . 1_655 N11 H6 2.6643 no . 2_676 N11 H7A 2.5771 no . 2_576 N11 H7B 3.5383 no . 2_576 N11 H7B 3.3747 no . 2_676 N11 H19A 3.1160 no . 2_566 C1 H14 3.0846 no . 2_576 C1 H18 3.3766 no . 2_666 C1 H19C 3.2071 no . 2_666 C2 H5 3.2414 no . 1_455 C2 H18 3.1583 no . 2_666 C3 H5 3.4961 no . 1_455 C3 H17 3.2680 no . 2_666 C3 H18 3.1664 no . 2_666 C4 H15 3.3406 no . 2_576 C4 H17 3.0916 no . 2_666 C4 H18 3.4276 no . 2_666 C5 H2 3.2199 no . 1_655 C5 H15 3.1238 no . 2_576 C6 H2 3.4534 no . 1_655 C6 H14 3.1916 no . 2_576 C6 H15 3.2595 no . 2_576 C6 H18 3.5826 no . 2_666 C6 H19C 3.3921 no . 2_666 C7 H14 3.0418 no . 2_576 C7 H19C 3.3890 no . 2_666 C9 H7A 3.1913 no . 2_576 C9 H7B 3.0013 no . 2_676 C9 H19A 3.0438 no . 2_566 C9 H19B 3.1014 no . 2_666 C9 H19C 3.5034 no . 2_666 C12 H6 3.1237 no . 2_676 C13 H2 3.1121 no . 2_566 C13 H5 3.5615 no . 2_676 C13 H6 3.0833 no . 2_676 C14 H2 3.4427 no . 2_566 C14 H5 3.2925 no . 2_676 C14 H6 3.4032 no . 2_676 C14 H7A 3.2525 no . 2_576 C14 H18 3.3089 no . 1_455 C15 H3 3.4130 no . 2_566 C15 H5 3.1211 no . 2_676 C15 H18 3.2347 no . 1_455 C15 H20C 3.4673 no . 2_576 C16 H3 2.9105 no . 2_566 C16 H5 3.2270 no . 2_676 C16 H20A 3.2799 no . 1_544 C16 H20C 3.4079 no . 2_576 C17 H2 3.2240 no . 2_566 C17 H3 3.1453 no . 2_566 C17 H5 3.5176 no . 2_676 C17 H15 3.2911 no . 1_655 C17 H20A 3.3187 no . 1_544 C18 H2 2.9547 no . 2_566 C18 H15 3.2076 no . 1_655 C19 H19B 3.3499 no . 2_666 C20 H16 3.5033 no . 1_566 C20 H17 3.4037 no . 1_566 H2 C5 3.2199 no . 1_455 H2 C6 3.4534 no . 1_455 H2 C13 3.1121 no . 2_566 H2 C14 3.4427 no . 2_566 H2 C17 3.2240 no . 2_566 H2 C18 2.9547 no . 2_566 H2 H5 3.0376 no . 1_455 H2 H6 3.4194 no . 1_455 H2 H18 3.2374 no . 2_566 H2 H18 3.5401 no . 2_666 H2 H19C 3.2077 no . 2_566 H3 O20 2.9499 no . 2_677 H3 C15 3.4130 no . 2_566 H3 C16 2.9105 no . 2_566 H3 C17 3.1453 no . 2_566 H3 H5 3.5231 no . 1_455 H3 H16 2.9757 no . 2_566 H3 H17 3.3267 no . 2_566 H3 H17 3.2658 no . 2_666 H3 H18 3.5167 no . 2_666 H5 C2 3.2414 no . 1_655 H5 C3 3.4961 no . 1_655 H5 C13 3.5615 no . 2_676 H5 C14 3.2925 no . 2_676 H5 C15 3.1211 no . 2_676 H5 C16 3.2270 no . 2_676 H5 C17 3.5176 no . 2_676 H5 H2 3.0376 no . 1_655 H5 H3 3.5231 no . 1_655 H5 H15 3.4183 no . 2_576 H5 H15 3.4690 no . 2_676 H5 H20C 3.2050 no . 1_655 H6 O9 2.9825 no . 2_676 H6 N11 2.6643 no . 2_676 H6 C12 3.1237 no . 2_676 H6 C13 3.0833 no . 2_676 H6 C14 3.4032 no . 2_676 H6 H2 3.4194 no . 1_655 H6 H7A 2.9090 no . 1_655 H6 H14 3.2259 no . 2_576 H6 H14 3.5806 no . 2_676 H6 H19C 3.4672 no . 2_666 H7A O9 2.6399 no . 2_576 H7A O10 3.3608 no . 2_576 H7A N11 2.5771 no . 2_576 H7A C9 3.1913 no . 2_576 H7A C14 3.2525 no . 2_576 H7A H6 2.9090 no . 1_455 H7A H14 2.6232 no . 2_576 H7B O9 2.5003 no . 2_676 H7B O10 3.3882 no . 2_676 H7B N11 3.5383 no . 2_576 H7B N11 3.3747 no . 2_676 H7B C9 3.0013 no . 2_676 H7B H14 2.9955 no . 2_576 H7B H19A 3.4921 no . 1_565 H7B H19C 3.4842 no . 2_666 H14 C1 3.0846 no . 2_576 H14 C6 3.1916 no . 2_576 H14 C7 3.0418 no . 2_576 H14 H6 3.2259 no . 2_576 H14 H6 3.5806 no . 2_676 H14 H7A 2.6232 no . 2_576 H14 H7B 2.9955 no . 2_576 H14 H18 3.1416 no . 1_455 H14 H19B 3.3562 no . 1_455 H15 O19 2.9912 no . 2_576 H15 C4 3.3406 no . 2_576 H15 C5 3.1238 no . 2_576 H15 C6 3.2595 no . 2_576 H15 C17 3.2911 no . 1_455 H15 C18 3.2076 no . 1_455 H15 H5 3.4183 no . 2_576 H15 H5 3.4690 no . 2_676 H15 H17 3.1598 no . 1_455 H15 H18 3.0270 no . 1_455 H15 H20C 3.1004 no . 2_576 H16 O19 3.1649 no . 2_676 H16 O20 2.5299 no . 1_444 H16 C20 3.5033 no . 1_544 H16 H3 2.9757 no . 2_566 H16 H20A 2.6614 no . 1_544 H16 H20A 3.5402 no . 2_576 H16 H20B 3.5958 no . 1_544 H16 H20C 2.9744 no . 2_576 H17 O4 2.9392 no . 2_666 H17 O19 3.2176 no . 2_676 H17 O20 3.5682 no . 1_544 H17 C3 3.2680 no . 2_666 H17 C4 3.0916 no . 2_666 H17 C20 3.4037 no . 1_544 H17 H3 3.3267 no . 2_566 H17 H3 3.2658 no . 2_666 H17 H15 3.1598 no . 1_655 H17 H20A 2.7313 no . 1_544 H17 H20B 3.3125 no . 1_544 H18 C1 3.3766 no . 2_666 H18 C2 3.1583 no . 2_666 H18 C3 3.1664 no . 2_666 H18 C4 3.4276 no . 2_666 H18 C6 3.5826 no . 2_666 H18 C14 3.3089 no . 1_655 H18 C15 3.2347 no . 1_655 H18 H2 3.2374 no . 2_566 H18 H2 3.5401 no . 2_666 H18 H3 3.5167 no . 2_666 H18 H14 3.1416 no . 1_655 H18 H15 3.0270 no . 1_655 H19A O8 3.1243 no . 2_566 H19A O8 3.5704 no . 2_666 H19A O9 3.1191 no . 1_545 H19A O10 2.5838 no . 2_566 H19A O10 3.5154 no . 2_666 H19A N11 3.1160 no . 2_566 H19A C9 3.0438 no . 2_566 H19A H7B 3.4921 no . 1_545 H19A H19B 3.1156 no . 2_666 H19B O8 2.7932 no . 2_666 H19B O10 2.6788 no . 2_666 H19B C9 3.1014 no . 2_666 H19B C19 3.3499 no . 2_666 H19B H14 3.3562 no . 1_655 H19B H19A 3.1156 no . 2_666 H19B H19B 2.7583 no . 2_666 H19C O8 3.4261 no . 2_566 H19C O8 2.8575 no . 2_666 H19C O9 3.1768 no . 1_545 H19C C1 3.2071 no . 2_666 H19C C6 3.3921 no . 2_666 H19C C7 3.3890 no . 2_666 H19C C9 3.5034 no . 2_666 H19C H2 3.2077 no . 2_566 H19C H6 3.4672 no . 2_666 H19C H7B 3.4842 no . 2_666 H20A O19 2.5549 no . 2_687 H20A O20 3.1801 no . 1_455 H20A C16 3.2799 no . 1_566 H20A C17 3.3187 no . 1_566 H20A H16 2.6614 no . 1_566 H20A H16 3.5402 no . 2_576 H20A H17 2.7313 no . 1_566 H20B S1 3.4114 no . 2_677 H20B O4 3.0182 no . 2_677 H20B O20 3.1675 no . 1_455 H20B O20 2.5853 no . 2_677 H20B H16 3.5958 no . 1_566 H20B H17 3.3125 no . 1_566 H20B H20B 3.2736 no . 2_577 H20C S1 3.5512 no . 1_455 H20C O4 3.5229 no . 1_455 H20C O19 3.3530 no . 1_455 H20C O20 3.3525 no . 1_455 H20C C15 3.4673 no . 2_576 H20C C16 3.4079 no . 2_576 H20C H5 3.2050 no . 1_455 H20C H15 3.1004 no . 2_576 H20C H16 2.9744 no . 2_576 #============================================================================== #============================================================================== # 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 #============================================================================== data_1 _database_code_depnum_ccdc_archive 'CCDC 923534' #TrackingRef '17582_web_deposit_cif_file_3_RoyMcBurney_1360161219.7a.cif' _chemical_formula_sum 'C15 H8 F5 N O3' _chemical_formula_moiety 'C15 H8 F5 N O3' _chemical_formula_weight 345.23 _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 7.89(3) _cell_length_b 5.60(2) _cell_length_c 16.51(6) _cell_angle_alpha 90.0000 _cell_angle_beta 102.65(7) _cell_angle_gamma 90.0000 _cell_volume 712(5) _cell_formula_units_Z 2 _cell_measurement_reflns_used 366 _cell_measurement_theta_min 5.49 _cell_measurement_theta_max 68.25 _cell_measurement_temperature 173 #------------------------------------------------------------------------------ _exptl_crystal_description platelet _exptl_crystal_colour colorless _exptl_crystal_size_max 0.120 _exptl_crystal_size_mid 0.030 _exptl_crystal_size_min 0.010 _exptl_crystal_density_diffrn 1.611 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 348.00 _exptl_absorpt_coefficient_mu 1.387 _exptl_absorpt_correction_type none #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 173 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54187 _diffrn_measurement_device_type ? _diffrn_reflns_number 7300 _diffrn_reflns_av_R_equivalents 0.1756 _diffrn_reflns_theta_max 68.50 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 67.00 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -19 _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 2479 _reflns_number_gt 864 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.1561 _refine_ls_wR_factor_ref 0.4300 _refine_ls_number_restraints 1 _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 2479 _refine_ls_number_parameters 218 _refine_ls_goodness_of_fit_ref 1.078 _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 0.004 _refine_diff_density_max 0.570 _refine_diff_density_min -0.420 _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.12(2) 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 F7 F 0.8390(11) 0.8554(14) 0.7401(5) 0.129(3) Uani 1.0 2 d . . . F8 F 0.9000(11) 0.8059(19) 0.9057(5) 0.141(3) Uani 1.0 2 d . . . F9 F 0.7779(9) 0.4283(17) 0.9758(4) 0.131(3) Uani 1.0 2 d . . . F10 F 0.5860(11) 0.0916(16) 0.8772(5) 0.136(3) Uani 1.0 2 d . . . F11 F 0.5194(11) 0.1368(17) 0.7110(5) 0.136(3) Uani 1.0 2 d . . . O2 O 0.8137(11) 0.2398(19) 0.4831(4) 0.127(3) Uani 1.0 2 d . . . O3 O 0.6090(15) 0.528(3) 0.4680(5) 0.144(4) Uani 1.0 2 d . . . O4 O 0.7503(11) 0.3947(19) 0.5921(4) 0.121(3) Uani 1.0 2 d . . . N1 N 0.7835(14) 0.249(3) 0.3922(5) 0.123(4) Uani 1.0 2 d . . . C3 C 0.711(2) 0.402(3) 0.5088(7) 0.126(5) Uani 1.0 2 d . . . C5 C 0.6332(19) 0.534(3) 0.6292(7) 0.124(5) Uani 1.0 2 d . . . C6 C 0.6801(16) 0.502(3) 0.7215(6) 0.109(4) Uani 1.0 2 d . . . C7 C 0.7730(15) 0.667(3) 0.7724(6) 0.104(4) Uani 1.0 2 d . . . C8 C 0.8076(17) 0.635(3) 0.8570(7) 0.112(4) Uani 1.0 2 d . . . C9 C 0.7447(18) 0.454(3) 0.8906(7) 0.117(4) Uani 1.0 2 d . . . C10 C 0.6475(16) 0.281(3) 0.8406(8) 0.115(4) Uani 1.0 2 d . . . C11 C 0.6193(17) 0.310(3) 0.7587(7) 0.118(4) Uani 1.0 2 d . . . C12 C 0.8359(17) 0.048(3) 0.3688(8) 0.123(4) Uani 1.0 2 d . . . C13 C 0.8165(16) 0.014(3) 0.2792(6) 0.111(4) Uani 1.0 2 d . . . C14 C 0.7285(17) 0.174(3) 0.2218(6) 0.121(5) Uani 1.0 2 d . . . C15 C 0.7041(17) 0.134(3) 0.1366(7) 0.118(4) Uani 1.0 2 d . . . C16 C 0.7714(19) -0.070(3) 0.1116(7) 0.120(4) Uani 1.0 2 d . . . C17 C 0.8543(17) -0.241(3) 0.1654(7) 0.120(4) Uani 1.0 2 d . . . C18 C 0.8779(18) -0.195(3) 0.2519(7) 0.118(4) Uani 1.0 2 d . . . H5A H 0.5121 0.4804 0.6073 0.1490 Uiso 1.0 2 calc R . . H5B H 0.6416 0.7044 0.6152 0.1490 Uiso 1.0 2 calc R . . H12 H 0.8847 -0.0722 0.4076 0.1473 Uiso 1.0 2 calc R . . H14 H 0.6833 0.3159 0.2407 0.1448 Uiso 1.0 2 calc R . . H15 H 0.6428 0.2451 0.0974 0.1414 Uiso 1.0 2 calc R . . H16 H 0.7602 -0.0960 0.0537 0.1436 Uiso 1.0 2 calc R . . H17 H 0.8946 -0.3851 0.1457 0.1434 Uiso 1.0 2 calc R . . H18 H 0.9361 -0.3085 0.2910 0.1418 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 F7 0.143(6) 0.137(6) 0.111(5) 0.005(5) 0.040(4) 0.015(4) F8 0.152(6) 0.165(7) 0.105(5) -0.012(6) 0.027(4) -0.008(5) F9 0.146(6) 0.166(7) 0.078(3) 0.016(5) 0.020(4) 0.000(4) F10 0.146(6) 0.146(7) 0.116(5) -0.010(5) 0.030(4) 0.010(5) F11 0.150(6) 0.144(6) 0.112(5) -0.007(5) 0.026(4) -0.023(5) O2 0.141(7) 0.156(8) 0.082(4) 0.012(6) 0.021(4) -0.007(5) O3 0.172(9) 0.176(9) 0.076(4) 0.026(8) 0.012(5) 0.002(6) O4 0.129(6) 0.157(8) 0.077(4) 0.010(6) 0.024(4) 0.002(5) N1 0.129(8) 0.160(10) 0.077(5) -0.008(8) 0.016(5) -0.002(6) C3 0.150(11) 0.149(11) 0.076(6) 0.006(10) 0.019(7) -0.009(8) C5 0.151(10) 0.145(11) 0.080(6) 0.040(9) 0.032(6) -0.002(7) C6 0.110(8) 0.144(11) 0.071(5) 0.017(7) 0.016(5) 0.000(6) C7 0.111(8) 0.118(9) 0.081(6) 0.003(7) 0.015(5) 0.009(6) C8 0.128(9) 0.124(9) 0.079(6) 0.013(8) 0.008(6) -0.004(7) C9 0.126(9) 0.140(11) 0.087(6) 0.015(8) 0.028(6) -0.002(8) C10 0.106(8) 0.124(9) 0.115(8) -0.012(7) 0.021(6) 0.008(8) C11 0.117(9) 0.143(11) 0.092(7) 0.020(9) 0.016(6) -0.011(8) C12 0.123(9) 0.150(11) 0.100(7) 0.025(9) 0.034(7) 0.010(8) C13 0.109(8) 0.148(11) 0.073(5) -0.008(7) 0.017(5) -0.005(6) C14 0.135(9) 0.144(12) 0.089(7) -0.022(8) 0.038(7) -0.003(7) C15 0.135(10) 0.126(9) 0.094(7) -0.017(8) 0.029(7) -0.005(7) C16 0.131(9) 0.135(11) 0.093(7) -0.020(8) 0.024(7) -0.016(8) C17 0.131(9) 0.140(10) 0.089(7) -0.006(9) 0.029(7) -0.009(8) C18 0.141(10) 0.117(9) 0.105(8) -0.003(8) 0.046(7) -0.000(7) #============================================================================== _computing_data_collection 'CrystalClear-SM Expert 2.1 b6 (Rigaku, 2011)' _computing_cell_refinement 'CrystalClear-SM Expert 2.1 b6' _computing_data_reduction 'CrystalClear-SM Expert 2.1 b6' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _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 F7 C7 1.337(15) yes . . F8 C8 1.357(16) yes . . F9 C9 1.381(14) yes . . F10 C10 1.362(18) yes . . F11 C11 1.382(16) yes . . O2 N1 1.468(12) yes . . O2 C3 1.35(2) yes . . O3 C3 1.167(18) yes . . O4 C3 1.342(13) yes . . O4 C5 1.443(18) yes . . N1 C12 1.28(2) yes . . C5 C6 1.497(15) yes . . C6 C7 1.354(17) yes . . C6 C11 1.37(2) yes . . C7 C8 1.376(15) yes . . C8 C9 1.30(2) yes . . C9 C10 1.39(2) yes . . C10 C11 1.330(17) yes . . C12 C13 1.466(17) yes . . C13 C14 1.378(18) yes . . C13 C18 1.38(2) yes . . C14 C15 1.396(16) yes . . C15 C16 1.36(3) yes . . C16 C17 1.370(19) yes . . C17 C18 1.423(17) yes . . C5 H5A 0.990 no . . C5 H5B 0.990 no . . C12 H12 0.950 no . . C14 H14 0.950 no . . C15 H15 0.950 no . . C16 H16 0.950 no . . C17 H17 0.950 no . . C18 H18 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 N1 O2 C3 109.0(9) yes . . . C3 O4 C5 113.2(10) yes . . . O2 N1 C12 106.7(10) yes . . . O2 C3 O3 127.8(11) yes . . . O2 C3 O4 106.5(11) yes . . . O3 C3 O4 125.8(15) yes . . . O4 C5 C6 109.2(11) yes . . . C5 C6 C7 121.9(13) yes . . . C5 C6 C11 121.1(12) yes . . . C7 C6 C11 116.8(10) yes . . . F7 C7 C6 119.8(10) yes . . . F7 C7 C8 120.1(11) yes . . . C6 C7 C8 120.0(12) yes . . . F8 C8 C7 118.0(12) yes . . . F8 C8 C9 120.1(10) yes . . . C7 C8 C9 121.7(12) yes . . . F9 C9 C8 120.6(12) yes . . . F9 C9 C10 119.4(13) yes . . . C8 C9 C10 120.0(12) yes . . . F10 C10 C9 118.9(11) yes . . . F10 C10 C11 123.3(13) yes . . . C9 C10 C11 117.8(14) yes . . . F11 C11 C6 120.3(10) yes . . . F11 C11 C10 116.2(13) yes . . . C6 C11 C10 123.5(13) yes . . . N1 C12 C13 116.6(13) yes . . . C12 C13 C14 122.3(14) yes . . . C12 C13 C18 118.3(12) yes . . . C14 C13 C18 119.2(11) yes . . . C13 C14 C15 121.7(14) yes . . . C14 C15 C16 117.6(12) yes . . . C15 C16 C17 123.5(12) yes . . . C16 C17 C18 117.6(14) yes . . . C13 C18 C17 120.3(12) yes . . . O4 C5 H5A 109.838 no . . . O4 C5 H5B 109.845 no . . . C6 C5 H5A 109.848 no . . . C6 C5 H5B 109.846 no . . . H5A C5 H5B 108.270 no . . . N1 C12 H12 121.705 no . . . C13 C12 H12 121.708 no . . . C13 C14 H14 119.159 no . . . C15 C14 H14 119.148 no . . . C14 C15 H15 121.193 no . . . C16 C15 H15 121.188 no . . . C15 C16 H16 118.264 no . . . C17 C16 H16 118.254 no . . . C16 C17 H17 121.192 no . . . C18 C17 H17 121.202 no . . . C13 C18 H18 119.867 no . . . C17 C18 H18 119.869 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 N1 O2 C3 O3 3(2) no . . . . N1 O2 C3 O4 -177.1(10) no . . . . C3 O2 N1 C12 -159.3(10) no . . . . C3 O4 C5 C6 176.5(11) no . . . . C5 O4 C3 O2 -171.2(11) no . . . . C5 O4 C3 O3 9(2) no . . . . O2 N1 C12 C13 179.3(9) no . . . . O4 C5 C6 C7 100.7(14) no . . . . O4 C5 C6 C11 -84.2(15) no . . . . C5 C6 C7 F7 -6.1(19) no . . . . C5 C6 C7 C8 177.5(11) no . . . . C5 C6 C11 F11 3(2) no . . . . C5 C6 C11 C10 -175.5(12) no . . . . C7 C6 C11 F11 178.2(11) no . . . . C7 C6 C11 C10 -0(2) no . . . . C11 C6 C7 F7 178.6(11) no . . . . C11 C6 C7 C8 2.3(18) no . . . . F7 C7 C8 F8 4.1(18) no . . . . F7 C7 C8 C9 179.6(11) no . . . . C6 C7 C8 F8 -179.5(11) no . . . . C6 C7 C8 C9 -4(2) no . . . . F8 C8 C9 F9 -3(2) no . . . . F8 C8 C9 C10 178.9(11) no . . . . C7 C8 C9 F9 -178.5(12) no . . . . C7 C8 C9 C10 3(3) no . . . . F9 C9 C10 F10 0.7(19) no . . . . F9 C9 C10 C11 -179.4(11) no . . . . C8 C9 C10 F10 178.8(13) no . . . . C8 C9 C10 C11 -1(2) no . . . . F10 C10 C11 F11 1(2) no . . . . F10 C10 C11 C6 179.6(11) no . . . . C9 C10 C11 F11 -178.8(12) no . . . . C9 C10 C11 C6 -0(2) no . . . . N1 C12 C13 C14 -7.5(19) no . . . . N1 C12 C13 C18 177.3(11) no . . . . C12 C13 C14 C15 -177.0(12) no . . . . C12 C13 C18 C17 176.9(11) no . . . . C14 C13 C18 C17 2(2) no . . . . C18 C13 C14 C15 -2(2) no . . . . C13 C14 C15 C16 -0(2) no . . . . C14 C15 C16 C17 3(2) no . . . . C15 C16 C17 C18 -3(3) no . . . . C16 C17 C18 C13 1(2) 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 F7 F8 2.685(14) no . . F7 O4 3.516(15) no . . F7 C5 2.816(16) no . . F7 C9 3.548(18) no . . F7 C11 3.56(2) no . . F8 F9 2.688(15) no . . F8 C6 3.585(16) no . . F8 C10 3.58(2) no . . F9 F10 2.723(13) no . . F9 C11 3.589(17) no . . F10 F11 2.689(14) no . . F10 C8 3.56(2) no . . F11 O4 3.290(15) no . . F11 C5 2.846(19) no . . F11 C7 3.600(18) no . . F11 C9 3.576(17) no . . O2 C5 3.472(18) no . . O3 N1 2.581(18) no . . O3 C5 2.626(17) no . . O4 N1 3.465(16) no . . O4 C7 3.314(16) no . . O4 C11 3.179(17) no . . N1 C14 2.782(17) no . . N1 C18 3.58(2) no . . C3 C12 3.35(3) no . . C6 C9 2.739(18) no . . C7 C10 2.72(2) no . . C8 C11 2.66(2) no . . C13 C16 2.752(19) no . . C14 C17 2.77(3) no . . C15 C18 2.785(19) no . . F7 F10 3.583(15) no . 1_565 F7 F11 2.922(15) no . 1_565 F7 C10 3.437(18) no . 1_565 F7 C11 3.133(19) no . 1_565 F7 C13 3.395(19) no . 2_756 F7 C14 3.48(2) no . 2_756 F7 C17 3.426(18) no . 2_766 F7 C18 3.349(19) no . 2_766 F8 F9 2.929(13) no . 2_757 F8 F10 2.900(15) no . 1_565 F8 C10 3.356(19) no . 1_565 F8 C15 3.48(2) no . 2_756 F8 C16 3.40(2) no . 2_756 F8 C17 3.54(2) no . 2_766 F9 F8 2.929(13) no . 2_747 F9 C15 3.282(17) no . 1_556 F9 C16 3.588(19) no . 1_556 F9 C16 3.599(19) no . 1_566 F9 C17 3.573(17) no . 1_566 F10 F7 3.583(15) no . 1_545 F10 F8 2.900(15) no . 1_545 F10 C7 3.455(17) no . 1_545 F10 C8 3.157(19) no . 1_545 F10 C14 3.537(18) no . 2_646 F10 C15 3.410(19) no . 2_646 F10 C16 3.43(2) no . 2_656 F10 C17 3.52(2) no . 2_656 F11 F7 2.922(15) no . 1_545 F11 O3 2.971(14) no . 2_646 F11 N1 3.400(16) no . 2_646 F11 C7 3.325(17) no . 1_545 F11 C13 3.419(19) no . 2_656 F11 C14 3.565(19) no . 2_646 F11 C18 3.45(2) no . 2_656 O3 F11 2.971(14) no . 2_656 O3 O3 3.56(2) no . 2_646 O3 O3 3.56(2) no . 2_656 O3 O4 3.466(18) no . 2_656 O3 C3 3.37(3) no . 2_656 O3 C5 3.54(2) no . 2_646 O3 C5 3.59(2) no . 2_656 O4 O3 3.466(18) no . 2_646 O4 C12 3.30(2) no . 2_756 O4 C18 3.490(17) no . 2_756 N1 F11 3.400(16) no . 2_656 N1 C5 3.45(3) no . 2_646 C3 O3 3.37(3) no . 2_646 C5 O3 3.59(2) no . 2_646 C5 O3 3.54(2) no . 2_656 C5 N1 3.45(3) no . 2_656 C6 C18 3.59(3) no . 2_756 C7 F10 3.455(17) no . 1_565 C7 F11 3.325(17) no . 1_565 C7 C18 3.51(3) no . 2_756 C8 F10 3.157(19) no . 1_565 C8 C16 3.45(3) no . 2_756 C8 C17 3.48(3) no . 2_756 C10 F7 3.437(18) no . 1_545 C10 F8 3.356(19) no . 1_545 C10 C15 3.49(3) no . 2_656 C11 F7 3.133(19) no . 1_545 C11 C13 3.55(3) no . 2_656 C11 C14 3.49(3) no . 2_656 C12 O4 3.30(2) no . 2_746 C13 F7 3.395(19) no . 2_746 C13 F11 3.419(19) no . 2_646 C13 C11 3.55(3) no . 2_646 C14 F7 3.48(2) no . 2_746 C14 F10 3.537(18) no . 2_656 C14 F11 3.565(19) no . 2_656 C14 C11 3.49(3) no . 2_646 C15 F8 3.48(2) no . 2_746 C15 F9 3.282(17) no . 1_554 C15 F10 3.410(19) no . 2_656 C15 C10 3.49(3) no . 2_646 C16 F8 3.40(2) no . 2_746 C16 F9 3.599(19) no . 1_544 C16 F9 3.588(19) no . 1_554 C16 F10 3.43(2) no . 2_646 C16 C8 3.45(3) no . 2_746 C17 F7 3.426(18) no . 2_736 C17 F8 3.54(2) no . 2_736 C17 F9 3.573(17) no . 1_544 C17 F10 3.52(2) no . 2_646 C17 C8 3.48(3) no . 2_746 C18 F7 3.349(19) no . 2_736 C18 F11 3.45(2) no . 2_646 C18 O4 3.490(17) no . 2_746 C18 C6 3.59(3) no . 2_746 C18 C7 3.51(3) no . 2_746 F7 H5B 2.4462 no . . F11 H5A 2.5681 no . . O2 H12 2.2857 no . . O3 H5A 2.5905 no . . O3 H5B 2.5829 no . . N1 H14 2.4808 no . . C3 H5A 2.5353 no . . C3 H5B 2.5826 no . . C3 H12 3.5664 no . . C7 H5A 3.2089 no . . C7 H5B 2.5834 no . . C11 H5A 2.6358 no . . C11 H5B 3.2720 no . . C12 H14 2.6565 no . . C12 H18 2.5885 no . . C13 H15 3.2807 no . . C13 H17 3.2895 no . . C14 H12 3.3428 no . . C14 H16 3.2174 no . . C14 H18 3.2368 no . . C15 H17 3.2608 no . . C16 H14 3.2182 no . . C16 H18 3.2493 no . . C17 H15 3.2618 no . . C18 H12 2.6494 no . . C18 H14 3.2324 no . . C18 H16 3.2468 no . . H12 H14 3.5943 no . . H12 H18 2.4413 no . . H14 H15 2.3511 no . . H15 H16 2.3056 no . . H16 H17 2.3123 no . . H17 H18 2.3880 no . . F7 H17 2.8892 no . 2_766 F7 H18 2.7117 no . 2_766 F8 H16 2.9447 no . 1_566 F8 H16 3.4514 no . 2_756 F8 H17 2.6343 no . 2_766 F9 H15 2.6746 no . 1_556 F9 H16 3.2203 no . 1_556 F9 H16 2.9751 no . 1_566 F9 H17 2.9457 no . 1_566 F10 H14 2.9788 no . 2_646 F10 H15 2.7441 no . 2_646 F10 H16 3.1196 no . 1_556 F11 H5B 3.1569 no . 1_545 F11 H14 2.6414 no . 2_646 F11 H18 3.5992 no . 2_656 O2 H5A 3.0439 no . 2_646 O2 H12 2.8536 no . 2_756 O3 H5A 3.3658 no . 2_646 O3 H5A 2.8926 no . 2_656 O3 H5B 2.8078 no . 2_646 O3 H12 3.4198 no . 1_565 O4 H12 2.8847 no . 2_756 O4 H18 3.0077 no . 2_756 N1 H5A 2.7752 no . 2_646 N1 H5B 3.3388 no . 2_646 N1 H18 3.3570 no . 1_565 C3 H5A 3.2994 no . 2_646 C3 H5B 3.2681 no . 2_646 C3 H12 3.1858 no . 2_756 C6 H14 3.5345 no . 2_656 C6 H18 3.5349 no . 2_756 C8 H17 3.5769 no . 2_766 C9 H15 3.5082 no . 2_656 C9 H17 3.5785 no . 2_756 C12 H5A 2.8829 no . 2_646 C13 H5A 3.5205 no . 2_646 C14 H17 3.1787 no . 1_565 C14 H18 3.3996 no . 1_565 C15 H17 3.0714 no . 1_565 C17 H14 3.2020 no . 1_545 C17 H15 3.3914 no . 1_545 C18 H14 3.1254 no . 1_545 H5A O2 3.0439 no . 2_656 H5A O3 2.8926 no . 2_646 H5A O3 3.3658 no . 2_656 H5A N1 2.7752 no . 2_656 H5A C3 3.2994 no . 2_656 H5A C12 2.8829 no . 2_656 H5A C13 3.5205 no . 2_656 H5A H12 3.1001 no . 2_656 H5B F11 3.1569 no . 1_565 H5B O3 2.8078 no . 2_656 H5B N1 3.3388 no . 2_656 H5B C3 3.2681 no . 2_656 H12 O2 2.8536 no . 2_746 H12 O3 3.4198 no . 1_545 H12 O4 2.8847 no . 2_746 H12 C3 3.1858 no . 2_746 H12 H5A 3.1001 no . 2_646 H14 F10 2.9788 no . 2_656 H14 F11 2.6414 no . 2_656 H14 C6 3.5345 no . 2_646 H14 C17 3.2020 no . 1_565 H14 C18 3.1254 no . 1_565 H14 H17 3.0312 no . 1_565 H14 H18 2.8925 no . 1_565 H15 F9 2.6746 no . 1_554 H15 F10 2.7441 no . 2_656 H15 C9 3.5082 no . 2_646 H15 C17 3.3914 no . 1_565 H15 H17 2.8597 no . 1_565 H16 F8 2.9447 no . 1_544 H16 F8 3.4514 no . 2_746 H16 F9 2.9751 no . 1_544 H16 F9 3.2203 no . 1_554 H16 F10 3.1196 no . 1_554 H17 F7 2.8892 no . 2_736 H17 F8 2.6343 no . 2_736 H17 F9 2.9457 no . 1_544 H17 C8 3.5769 no . 2_736 H17 C9 3.5785 no . 2_746 H17 C14 3.1787 no . 1_545 H17 C15 3.0714 no . 1_545 H17 H14 3.0312 no . 1_545 H17 H15 2.8597 no . 1_545 H18 F7 2.7117 no . 2_736 H18 F11 3.5992 no . 2_646 H18 O4 3.0077 no . 2_746 H18 N1 3.3570 no . 1_545 H18 C6 3.5349 no . 2_746 H18 C14 3.3996 no . 1_545 H18 H14 2.8925 no . 1_545 #============================================================================== #============================================================================== # 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 #==============================================================================