# 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_SX029-03 #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C19 H14 F3 N O5' _chemical_formula_moiety 'C19 H14 F3 N O5' _chemical_formula_weight 393.32 _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 5.512(3) _cell_length_b 10.789(7) _cell_length_c 14.890(9) _cell_angle_alpha 88.566(12) _cell_angle_beta 81.672(12) _cell_angle_gamma 83.072(9) _cell_volume 869.7(9) _cell_formula_units_Z 2 _cell_measurement_reflns_used 1912 _cell_measurement_theta_min 2.80 _cell_measurement_theta_max 27.50 _cell_measurement_temperature 93 #------------------------------------------------------------------------------ _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_min 0.100 _exptl_crystal_density_diffrn 1.502 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 404.00 _exptl_absorpt_coefficient_mu 0.129 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'REQAB (Rigaku, 1998)' _exptl_absorpt_correction_T_min 0.881 _exptl_absorpt_correction_T_max 0.987 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 93 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_measurement_device_type 'Rigaku XtaLAB mini' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 6.827 _diffrn_reflns_number 9198 _diffrn_reflns_av_R_equivalents 0.0297 _diffrn_reflns_theta_max 27.53 _diffrn_reflns_theta_min 2.77 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measured_fraction_theta_full 0.994 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _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 3982 _reflns_number_gt 3025 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0454 _refine_ls_wR_factor_ref 0.1266 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 3982 _refine_ls_number_parameters 254 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0666P)^2^+0.1265P] 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 0.27 _refine_diff_density_min -0.32 _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 0.0033 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 0.92159(18) 0.49694(9) 0.15854(7) 0.0270(2) Uani 1 2 d . . . F2 F 0.97440(19) 0.37795(9) 0.04273(7) 0.0320(3) Uani 1 2 d . . . F20 F 0.63288(19) 0.49946(10) 0.07497(7) 0.0336(3) Uani 1 2 d . . . O1 O 0.5287(2) 0.46926(10) 0.28676(7) 0.0226(3) Uani 1 2 d . . . O3 O 0.1688(2) 0.45799(12) 0.37668(8) 0.0324(3) Uani 1 2 d . . . O4 O 0.7700(3) 0.95284(12) 0.53859(9) 0.0349(3) Uani 1 2 d . . . O5 O 0.4668(3) 0.91738(13) 0.64205(8) 0.0353(3) Uani 1 2 d . . . O21 O 0.8829(2) 0.24724(10) 0.21096(7) 0.0199(2) Uani 1 2 d . . . N1 N 0.5955(3) 0.89612(13) 0.56805(9) 0.0257(3) Uani 1 2 d . . . C1 C 0.5346(3) 0.79669(15) 0.51189(11) 0.0223(3) Uani 1 2 d . . . C2 C 0.4259(3) 0.60890(14) 0.40991(11) 0.0207(3) Uani 1 2 d . . . C3 C 0.3565(3) 0.50562(15) 0.35798(11) 0.0222(3) Uani 1 2 d . . . C4 C 0.2714(3) 0.64488(15) 0.48998(11) 0.0228(3) Uani 1 2 d . . . C5 C 0.8287(3) 0.14469(14) 0.16241(10) 0.0194(3) Uani 1 2 d . . . C6 C 0.6349(3) 0.66841(15) 0.38077(11) 0.0229(3) Uani 1 2 d . . . C7 C 0.3260(3) 0.73896(15) 0.54225(11) 0.0236(3) Uani 1 2 d . . . C8 C 0.6906(3) 0.32260(14) 0.16764(10) 0.0188(3) Uani 1 2 d . . . C9 C 0.4687(3) 0.36834(15) 0.23524(11) 0.0226(3) Uani 1 2 d . . . C10 C 0.9501(3) 0.01966(14) 0.17520(11) 0.0213(3) Uani 1 2 d . . . C11 C 0.6902(3) 0.76440(15) 0.43216(11) 0.0239(3) Uani 1 2 d . . . C12 C 0.8065(3) 0.42442(15) 0.11092(11) 0.0224(3) Uani 1 2 d . . . C13 C 0.6579(3) 0.20723(15) 0.11740(11) 0.0210(3) Uani 1 2 d . . . C14 C 1.1780(4) -0.22015(17) 0.20187(13) 0.0347(4) Uani 1 2 d . . . C15 C 0.4976(3) 0.18315(17) 0.04884(12) 0.0290(4) Uani 1 2 d . . . C16 C 0.8849(4) -0.08134(16) 0.13151(12) 0.0314(4) Uani 1 2 d . . . C17 C 1.1287(4) -0.00021(16) 0.23245(13) 0.0305(4) Uani 1 2 d . . . C18 C 0.9992(4) -0.20100(17) 0.14515(13) 0.0375(5) Uani 1 2 d . . . C19 C 1.2430(4) -0.12040(18) 0.24536(14) 0.0369(4) Uani 1 2 d . . . H4 H 0.12821 0.60456 0.5086 0.0273 Uiso 1 2 calc R . . H6 H 0.73886 0.64348 0.32608 0.0274 Uiso 1 2 calc R . . H7 H 0.22367 0.7634 0.59738 0.0283 Uiso 1 2 calc R . . H9A H 0.3273 0.39784 0.203 0.0271 Uiso 1 2 calc R . . H9B H 0.42144 0.29928 0.27663 0.0271 Uiso 1 2 calc R . . H11 H 0.83067 0.80662 0.41312 0.0287 Uiso 1 2 calc R . . H14 H 1.25603 -0.30201 0.21088 0.0417 Uiso 1 2 calc R . . H15A H 0.56208 0.10431 0.01798 0.0348 Uiso 1 2 calc R . . H15B H 0.49621 0.25148 0.00423 0.0348 Uiso 1 2 calc R . . H15C H 0.32911 0.17783 0.07923 0.0348 Uiso 1 2 calc R . . H16 H 0.76236 -0.06849 0.09238 0.0377 Uiso 1 2 calc R . . H17 H 1.17309 0.06821 0.26288 0.0366 Uiso 1 2 calc R . . H18 H 0.9542 -0.26986 0.11538 0.0450 Uiso 1 2 calc R . . H19 H 1.36608 -0.13367 0.28425 0.0443 Uiso 1 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 0.0277(5) 0.0228(5) 0.0315(5) -0.0081(4) -0.0038(4) 0.0001(4) F2 0.0376(6) 0.0267(5) 0.0280(5) -0.0049(4) 0.0090(4) -0.0009(4) F20 0.0319(6) 0.0312(6) 0.0384(6) -0.0012(4) -0.0117(5) 0.0136(5) O1 0.0217(6) 0.0211(6) 0.0239(6) -0.0026(4) 0.0010(4) -0.0028(4) O3 0.0258(7) 0.0377(7) 0.0331(7) -0.0101(5) 0.0041(5) -0.0073(5) O4 0.0357(7) 0.0347(7) 0.0362(7) -0.0143(6) -0.0036(6) -0.0007(6) O5 0.0431(8) 0.0396(8) 0.0240(7) -0.0107(6) -0.0012(6) -0.0052(5) O21 0.0227(6) 0.0155(5) 0.0223(6) -0.0006(4) -0.0073(4) -0.0012(4) N1 0.0283(8) 0.0254(8) 0.0236(7) -0.0031(6) -0.0054(6) 0.0032(6) C1 0.0253(8) 0.0195(8) 0.0222(8) -0.0008(6) -0.0060(6) 0.0015(6) C2 0.0208(8) 0.0180(8) 0.0224(8) 0.0006(6) -0.0028(6) 0.0031(6) C3 0.0219(8) 0.0224(8) 0.0209(8) 0.0003(6) -0.0012(6) 0.0025(6) C4 0.0198(8) 0.0241(8) 0.0233(8) -0.0017(6) -0.0007(6) 0.0028(6) C5 0.0204(8) 0.0193(8) 0.0190(8) -0.0040(6) -0.0025(6) -0.0022(6) C6 0.0219(8) 0.0236(8) 0.0212(8) 0.0004(6) 0.0006(6) 0.0023(6) C7 0.0240(8) 0.0252(8) 0.0200(8) 0.0000(6) -0.0006(6) 0.0015(6) C8 0.0180(8) 0.0190(7) 0.0196(7) -0.0009(6) -0.0042(6) 0.0002(6) C9 0.0221(8) 0.0204(8) 0.0255(8) -0.0040(6) -0.0027(6) -0.0019(6) C10 0.0237(8) 0.0185(8) 0.0209(8) -0.0027(6) -0.0009(6) 0.0007(6) C11 0.0225(8) 0.0236(8) 0.0255(8) -0.0042(6) -0.0029(6) 0.0041(6) C12 0.0222(8) 0.0224(8) 0.0218(8) 0.0002(6) -0.0034(6) 0.0005(6) C13 0.0215(8) 0.0208(8) 0.0210(8) -0.0036(6) -0.0024(6) -0.0014(6) C14 0.0472(12) 0.0198(9) 0.0331(10) 0.0063(8) -0.0011(8) 0.0039(7) C15 0.0284(9) 0.0305(9) 0.0303(9) -0.0032(7) -0.0115(7) -0.0010(7) C16 0.0416(11) 0.0235(9) 0.0313(10) -0.0037(7) -0.0124(8) -0.0023(7) C17 0.0362(10) 0.0214(9) 0.0360(10) -0.0018(7) -0.0139(8) -0.0004(7) C18 0.0600(13) 0.0178(9) 0.0349(10) -0.0020(8) -0.0090(9) -0.0050(7) C19 0.0398(11) 0.0284(10) 0.0434(11) 0.0026(8) -0.0153(9) 0.0050(8) #============================================================================== _computing_data_collection 'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)' _computing_cell_refinement 'CrystalClear-SM Expert 2.0 r4' _computing_data_reduction 'CrystalClear-SM Expert 2.0 r4' _computing_structure_solution 'Il Milione (Burla, et al., 2007)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2011)' _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 C12 1.340(2) yes . . F2 C12 1.3342(19) yes . . F20 C12 1.341(2) yes . . O1 C3 1.3486(19) yes . . O1 C9 1.444(2) yes . . O3 C3 1.204(2) yes . . O4 N1 1.224(2) yes . . O5 N1 1.2315(18) yes . . O21 C5 1.421(2) yes . . O21 C8 1.4710(19) yes . . N1 C1 1.475(2) yes . . C1 C7 1.387(2) yes . . C1 C11 1.386(2) yes . . C2 C3 1.489(2) yes . . C2 C4 1.395(2) yes . . C2 C6 1.395(2) yes . . C4 C7 1.381(3) yes . . C5 C8 1.977(2) yes . . C5 C10 1.453(2) yes . . C5 C13 1.341(2) yes . . C6 C11 1.391(3) yes . . C8 C9 1.509(2) yes . . C8 C12 1.515(2) yes . . C8 C13 1.511(2) yes . . C10 C16 1.392(3) yes . . C10 C17 1.387(3) yes . . C13 C15 1.490(3) yes . . C14 C18 1.382(3) yes . . C14 C19 1.379(3) yes . . C16 C18 1.390(3) yes . . C17 C19 1.393(3) yes . . 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 C3 O1 C9 114.24(13) yes . . . C5 O21 C8 86.24(11) yes . . . O4 N1 O5 123.76(15) yes . . . O4 N1 C1 118.36(13) yes . . . O5 N1 C1 117.88(15) yes . . . N1 C1 C7 118.25(14) yes . . . N1 C1 C11 118.50(15) yes . . . C7 C1 C11 123.25(16) yes . . . C3 C2 C4 117.01(15) yes . . . C3 C2 C6 122.30(14) yes . . . C4 C2 C6 120.69(16) yes . . . O1 C3 O3 122.71(16) yes . . . O1 C3 C2 112.68(14) yes . . . O3 C3 C2 124.61(14) yes . . . C2 C4 C7 120.19(16) yes . . . O21 C5 C8 47.95(8) yes . . . O21 C5 C10 120.75(14) yes . . . O21 C5 C13 97.68(13) yes . . . C8 C5 C10 168.32(14) yes . . . C8 C5 C13 49.77(10) yes . . . C10 C5 C13 141.54(16) yes . . . C2 C6 C11 119.69(14) yes . . . C1 C7 C4 118.05(15) yes . . . O21 C8 C5 45.81(8) yes . . . O21 C8 C9 112.17(13) yes . . . O21 C8 C12 108.81(13) yes . . . O21 C8 C13 88.45(11) yes . . . C5 C8 C9 121.38(12) yes . . . C5 C8 C12 123.80(11) yes . . . C5 C8 C13 42.67(9) yes . . . C9 C8 C12 114.66(13) yes . . . C9 C8 C13 113.47(14) yes . . . C12 C8 C13 116.26(13) yes . . . O1 C9 C8 109.10(13) yes . . . C5 C10 C16 120.29(16) yes . . . C5 C10 C17 120.17(15) yes . . . C16 C10 C17 119.53(15) yes . . . C1 C11 C6 118.12(16) yes . . . F1 C12 F2 106.34(14) yes . . . F1 C12 F20 107.00(13) yes . . . F1 C12 C8 113.25(14) yes . . . F2 C12 F20 107.73(14) yes . . . F2 C12 C8 112.01(13) yes . . . F20 C12 C8 110.21(14) yes . . . C5 C13 C8 87.56(14) yes . . . C5 C13 C15 139.12(16) yes . . . C8 C13 C15 133.32(14) yes . . . C18 C14 C19 119.98(17) yes . . . C10 C16 C18 119.99(19) yes . . . C10 C17 C19 120.06(18) yes . . . C14 C18 C16 120.23(19) yes . . . C14 C19 C17 120.2(2) yes . . . #============================================================================== #============================================================================== # 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 948159' ####################################################################### # # 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_SX031 #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C20 H13 F6 N O6' _chemical_formula_moiety 'C20 H13 F6 N O6' _chemical_formula_weight 477.32 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,+Y,1/2-Z 3 -X,-Y,-Z 4 +X,-Y,1/2+Z 5 1/2+X,1/2+Y,+Z 6 1/2-X,1/2+Y,1/2-Z 7 1/2-X,1/2-Y,-Z 8 1/2+X,1/2-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 22.067(11) _cell_length_b 6.117(3) _cell_length_c 29.455(15) _cell_angle_alpha 90.0000 _cell_angle_beta 92.449(6) _cell_angle_gamma 90.0000 _cell_volume 3972(3) _cell_formula_units_Z 8 _cell_measurement_reflns_used 4541 _cell_measurement_theta_min 2.70 _cell_measurement_theta_max 27.50 _cell_measurement_temperature 93 #------------------------------------------------------------------------------ _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.260 _exptl_crystal_size_mid 0.090 _exptl_crystal_size_min 0.060 _exptl_crystal_density_diffrn 1.596 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1936.00 _exptl_absorpt_coefficient_mu 0.153 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'REQAB (Rigaku, 1998)' _exptl_absorpt_correction_T_min 0.903 _exptl_absorpt_correction_T_max 0.991 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 93 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_measurement_device_type 'Rigaku XtaLAB mini' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 6.827 _diffrn_reflns_number 13294 _diffrn_reflns_av_R_equivalents 0.0249 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_min 2.77 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_limit_l_max 38 _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 4538 _reflns_number_gt 3433 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0417 _refine_ls_wR_factor_ref 0.1140 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 4538 _refine_ls_number_parameters 299 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0514P)^2^+4.4287P] 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 0.34 _refine_diff_density_min -0.29 _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 0.0033 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 F3 F 0.45659(5) 0.1181(2) 0.09032(4) 0.0360(3) Uani 1 8 d . . . F5 F 0.50093(6) 0.1700(2) 0.02825(4) 0.0491(4) Uani 1 8 d . . . F22 F 0.49147(6) 0.75643(18) 0.14037(4) 0.0360(3) Uani 1 8 d . . . F23 F 0.43350(5) 0.5035(2) 0.16327(5) 0.0496(4) Uani 1 8 d . . . F24 F 0.50798(6) 0.6123(2) 0.20647(4) 0.0437(3) Uani 1 8 d . . . F25 F 0.44936(5) 0.4288(2) 0.05667(5) 0.0462(3) Uani 1 8 d . . . O2 O 0.67348(6) -0.2121(2) 0.30365(4) 0.0299(3) Uani 1 8 d . . . O4 O 0.73654(7) -0.1892(2) -0.13316(5) 0.0383(4) Uani 1 8 d . . . O26 O 0.58027(5) 0.1695(2) 0.11095(4) 0.0210(3) Uani 1 8 d . . . O27 O 0.60520(5) 0.4012(2) 0.03175(4) 0.0225(3) Uani 1 8 d . . . O28 O 0.66873(6) 0.6826(2) 0.02351(4) 0.0293(3) Uani 1 8 d . . . O29 O 0.80126(6) 0.0688(2) -0.14381(5) 0.0321(3) Uani 1 8 d . . . N30 N 0.75748(7) -0.0079(3) -0.12497(5) 0.0252(3) Uani 1 8 d . . . C2 C 0.67687(7) 0.3690(3) -0.02443(5) 0.0194(3) Uani 1 8 d . . . C3 C 0.65116(7) 0.5045(3) 0.01200(5) 0.0198(3) Uani 1 8 d . . . C4 C 0.75442(8) 0.3268(3) -0.07866(6) 0.0223(3) Uani 1 8 d . . . C5 C 0.65251(8) 0.1660(3) -0.03652(6) 0.0226(3) Uani 1 8 d . . . C6 C 0.72905(7) 0.1261(3) -0.09018(5) 0.0205(3) Uani 1 8 d . . . C7 C 0.72766(7) 0.4488(3) -0.04552(6) 0.0209(3) Uani 1 8 d . . . C8 C 0.56722(7) 0.2357(3) 0.15507(5) 0.0192(3) Uani 1 8 d . . . C9 C 0.59402(7) 0.1181(3) 0.19349(6) 0.0205(3) Uani 1 8 d . . . C10 C 0.62879(8) -0.0669(3) 0.18592(6) 0.0232(4) Uani 1 8 d . . . C11 C 0.67860(8) 0.0430(3) -0.06996(6) 0.0243(4) Uani 1 8 d . . . C12 C 0.57957(8) 0.5157(3) 0.06886(6) 0.0219(3) Uani 1 8 d . . . C13 C 0.54244(7) 0.3521(3) 0.09418(5) 0.0202(3) Uani 1 8 d . . . C14 C 0.65586(8) -0.1837(3) 0.22194(6) 0.0246(4) Uani 1 8 d . . . C15 C 0.64804(8) -0.1135(3) 0.26607(6) 0.0238(4) Uani 1 8 d . . . C16 C 0.58633(8) 0.1860(3) 0.23827(6) 0.0272(4) Uani 1 8 d . . . C17 C 0.61304(9) 0.0705(3) 0.27421(6) 0.0289(4) Uani 1 8 d . . . C18 C 0.53117(7) 0.4054(3) 0.14292(5) 0.0211(3) Uani 1 8 d . . . C19 C 0.49158(8) 0.5677(3) 0.16332(6) 0.0271(4) Uani 1 8 d . . . C20 C 0.71111(11) -0.3985(3) 0.29644(7) 0.0391(5) Uani 1 8 d . . . C21 C 0.48732(8) 0.2636(3) 0.06697(6) 0.0271(4) Uani 1 8 d . . . H4 H 0.78924 0.37909 -0.09315 0.0267 Uiso 1 8 calc R . . H5 H 0.61804 0.11211 -0.02183 0.0271 Uiso 1 8 calc R . . H7 H 0.74395 0.58743 -0.03709 0.0251 Uiso 1 8 calc R . . H10 H 0.63417 -0.11436 0.15565 0.0278 Uiso 1 8 calc R . . H11 H 0.66224 -0.09501 -0.07877 0.0291 Uiso 1 8 calc R . . H12A H 0.55354 0.63708 0.05734 0.0262 Uiso 1 8 calc R . . H12B H 0.61213 0.57706 0.08922 0.0262 Uiso 1 8 calc R . . H14 H 0.67942 -0.31007 0.21634 0.0295 Uiso 1 8 calc R . . H16 H 0.56265 0.31195 0.244 0.0326 Uiso 1 8 calc R . . H17 H 0.60748 0.11694 0.30452 0.0347 Uiso 1 8 calc R . . H20A H 0.68781 -0.50932 0.27917 0.0469 Uiso 1 8 calc R . . H20B H 0.72503 -0.45936 0.32584 0.0469 Uiso 1 8 calc R . . H20C H 0.74624 -0.35432 0.27936 0.0469 Uiso 1 8 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 F3 0.0271(6) 0.0394(7) 0.0410(6) -0.0130(5) -0.0065(5) 0.0127(5) F5 0.0429(7) 0.0702(10) 0.0341(7) -0.0254(7) 0.0004(5) -0.0190(6) F22 0.0499(7) 0.0262(6) 0.0325(6) 0.0088(5) 0.0087(5) 0.0099(5) F23 0.0246(6) 0.0450(8) 0.0807(10) 0.0065(6) 0.0210(6) 0.0067(7) F24 0.0640(8) 0.0452(7) 0.0226(5) 0.0230(7) 0.0101(5) 0.0009(5) F25 0.0338(7) 0.0442(8) 0.0584(8) -0.0001(6) -0.0231(6) 0.0173(6) O2 0.0333(7) 0.0303(7) 0.0256(6) 0.0051(6) -0.0047(5) 0.0069(5) O4 0.0477(9) 0.0250(7) 0.0434(8) -0.0082(7) 0.0154(7) -0.0120(6) O26 0.0212(6) 0.0236(6) 0.0182(6) 0.0009(5) -0.0001(4) 0.0010(5) O27 0.0246(6) 0.0243(6) 0.0191(6) -0.0061(5) 0.0050(5) -0.0010(5) O28 0.0302(7) 0.0246(7) 0.0339(7) -0.0079(6) 0.0090(5) -0.0061(5) O29 0.0228(6) 0.0404(8) 0.0337(7) -0.0048(6) 0.0083(5) -0.0086(6) N30 0.0241(8) 0.0254(8) 0.0260(7) 0.0007(6) 0.0002(6) -0.0035(6) C2 0.0172(7) 0.0204(8) 0.0204(8) -0.0010(7) -0.0036(6) 0.0021(6) C3 0.0177(8) 0.0213(9) 0.0200(8) -0.0025(7) -0.0019(6) 0.0034(6) C4 0.0191(8) 0.0240(9) 0.0237(8) -0.0018(7) 0.0007(6) 0.0025(7) C5 0.0183(8) 0.0231(9) 0.0265(8) -0.0047(7) 0.0016(6) 0.0003(7) C6 0.0191(8) 0.0214(9) 0.0208(8) 0.0001(7) -0.0009(6) -0.0013(6) C7 0.0200(8) 0.0204(9) 0.0222(8) -0.0043(7) -0.0007(6) 0.0013(6) C8 0.0175(8) 0.0225(8) 0.0179(7) -0.0022(7) 0.0027(6) -0.0006(6) C9 0.0174(8) 0.0230(9) 0.0212(8) -0.0010(7) 0.0010(6) 0.0034(7) C10 0.0232(8) 0.0249(9) 0.0216(8) 0.0002(7) 0.0010(6) -0.0004(7) C11 0.0213(8) 0.0219(9) 0.0295(9) -0.0038(7) -0.0005(7) -0.0022(7) C12 0.0227(8) 0.0232(9) 0.0198(8) -0.0024(7) 0.0025(6) 0.0005(7) C13 0.0184(8) 0.0222(9) 0.0198(8) 0.0010(7) -0.0002(6) 0.0024(6) C14 0.0239(9) 0.0213(9) 0.0282(9) 0.0023(7) -0.0013(7) 0.0006(7) C15 0.0210(8) 0.0254(9) 0.0246(8) -0.0022(7) -0.0034(6) 0.0060(7) C16 0.0284(9) 0.0317(10) 0.0215(8) 0.0099(8) 0.0028(7) 0.0008(7) C17 0.0325(10) 0.0363(11) 0.0182(8) 0.0088(8) 0.0019(7) 0.0018(7) C18 0.0187(8) 0.0262(9) 0.0186(8) -0.0014(7) 0.0025(6) 0.0040(7) C19 0.0273(9) 0.0268(10) 0.0277(9) 0.0037(8) 0.0074(7) 0.0075(7) C20 0.0544(13) 0.0241(10) 0.0372(11) 0.0110(10) -0.0162(10) 0.0029(8) C21 0.0243(9) 0.0293(10) 0.0273(9) -0.0046(8) -0.0024(7) 0.0052(7) #============================================================================== _computing_data_collection 'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)' _computing_cell_refinement 'CrystalClear-SM Expert 2.0 r4' _computing_data_reduction 'CrystalClear-SM Expert 2.0 r4' _computing_structure_solution 'Il Milione (Burla, et al., 2007)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2011)' _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 F3 C21 1.329(2) yes . . F5 C21 1.322(2) yes . . F22 C19 1.338(2) yes . . F23 C19 1.340(2) yes . . F24 C19 1.335(2) yes . . F25 C21 1.339(2) yes . . O2 C15 1.360(2) yes . . O2 C20 1.431(3) yes . . O4 N30 1.222(2) yes . . O26 C8 1.403(2) yes . . O26 C13 1.468(2) yes . . O27 C3 1.348(2) yes . . O27 C12 1.434(2) yes . . O28 C3 1.200(2) yes . . O29 N30 1.228(2) yes . . N30 C6 1.473(2) yes . . C2 C3 1.487(2) yes . . C2 C5 1.393(2) yes . . C2 C7 1.393(2) yes . . C4 C6 1.386(2) yes . . C4 C7 1.381(3) yes . . C5 C11 1.384(3) yes . . C6 C11 1.382(2) yes . . C8 C9 1.446(2) yes . . C8 C13 1.985(2) yes . . C8 C18 1.347(2) yes . . C9 C10 1.390(2) yes . . C9 C16 1.400(3) yes . . C10 C14 1.392(3) yes . . C12 C13 1.510(2) yes . . C13 C18 1.503(2) yes . . C13 C21 1.527(2) yes . . C14 C15 1.387(3) yes . . C15 C17 1.392(3) yes . . C16 C17 1.383(3) yes . . C18 C19 1.468(3) yes . . C4 H4 0.950 no . . C5 H5 0.950 no . . C7 H7 0.950 no . . C10 H10 0.950 no . . C11 H11 0.950 no . . C12 H12A 0.990 no . . C12 H12B 0.990 no . . C14 H14 0.950 no . . C16 H16 0.950 no . . C17 H17 0.950 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 C15 O2 C20 117.00(14) yes . . . C8 O26 C13 87.46(11) yes . . . C3 O27 C12 115.38(13) yes . . . O4 N30 O29 123.78(16) yes . . . O4 N30 C6 118.27(15) yes . . . O29 N30 C6 117.95(15) yes . . . C3 C2 C5 121.73(15) yes . . . C3 C2 C7 117.77(15) yes . . . C5 C2 C7 120.47(15) yes . . . O27 C3 O28 122.92(15) yes . . . O27 C3 C2 111.57(14) yes . . . O28 C3 C2 125.51(15) yes . . . C6 C4 C7 118.11(16) yes . . . C2 C5 C11 119.91(16) yes . . . N30 C6 C4 118.92(15) yes . . . N30 C6 C11 118.05(15) yes . . . C4 C6 C11 123.02(16) yes . . . C2 C7 C4 120.18(16) yes . . . O26 C8 C9 119.21(14) yes . . . O26 C8 C13 47.62(9) yes . . . O26 C8 C18 96.82(12) yes . . . C9 C8 C13 166.77(14) yes . . . C9 C8 C18 143.96(15) yes . . . C13 C8 C18 49.20(9) yes . . . C8 C9 C10 119.30(16) yes . . . C8 C9 C16 121.84(16) yes . . . C10 C9 C16 118.85(16) yes . . . C9 C10 C14 121.14(17) yes . . . C5 C11 C6 118.29(16) yes . . . O27 C12 C13 107.03(14) yes . . . O26 C13 C8 44.92(8) yes . . . O26 C13 C12 110.96(13) yes . . . O26 C13 C18 87.62(11) yes . . . O26 C13 C21 109.62(14) yes . . . C8 C13 C12 123.34(12) yes . . . C8 C13 C18 42.70(9) yes . . . C8 C13 C21 121.99(13) yes . . . C12 C13 C18 116.33(14) yes . . . C12 C13 C21 114.36(14) yes . . . C18 C13 C21 114.68(14) yes . . . C10 C14 C15 119.27(17) yes . . . O2 C15 C14 124.19(17) yes . . . O2 C15 C17 115.54(16) yes . . . C14 C15 C17 120.26(16) yes . . . C9 C16 C17 120.30(17) yes . . . C15 C17 C16 120.17(17) yes . . . C8 C18 C13 88.10(13) yes . . . C8 C18 C19 140.14(15) yes . . . C13 C18 C19 131.54(14) yes . . . F22 C19 F23 105.73(15) yes . . . F22 C19 F24 107.42(15) yes . . . F22 C19 C18 111.42(15) yes . . . F23 C19 F24 106.33(15) yes . . . F23 C19 C18 112.78(16) yes . . . F24 C19 C18 112.71(15) yes . . . F3 C21 F5 107.21(16) yes . . . F3 C21 F25 107.14(15) yes . . . F3 C21 C13 112.24(14) yes . . . F5 C21 F25 107.13(15) yes . . . F5 C21 C13 113.65(15) yes . . . F25 C21 C13 109.16(15) yes . . . C6 C4 H4 120.938 no . . . C7 C4 H4 120.948 no . . . C2 C5 H5 120.040 no . . . C11 C5 H5 120.045 no . . . C2 C7 H7 119.920 no . . . C4 C7 H7 119.899 no . . . C9 C10 H10 119.427 no . . . C14 C10 H10 119.435 no . . . C5 C11 H11 120.846 no . . . C6 C11 H11 120.862 no . . . O27 C12 H12A 110.296 no . . . O27 C12 H12B 110.316 no . . . C13 C12 H12A 110.315 no . . . C13 C12 H12B 110.317 no . . . H12A C12 H12B 108.564 no . . . C10 C14 H14 120.362 no . . . C15 C14 H14 120.368 no . . . C9 C16 H16 119.850 no . . . C17 C16 H16 119.852 no . . . C15 C17 H17 119.917 no . . . C16 C17 H17 119.908 no . . . O2 C20 H20A 109.460 no . . . O2 C20 H20B 109.481 no . . . O2 C20 H20C 109.472 no . . . H20A C20 H20B 109.475 no . . . H20A C20 H20C 109.462 no . . . H20B C20 H20C 109.478 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 O2 C15 C14 0.7(2) no . . . . C20 O2 C15 C17 -178.37(14) no . . . . C8 O26 C13 C8 0.00(7) no . . . . C8 O26 C13 C12 116.71(12) no . . . . C8 O26 C13 C18 -0.64(10) no . . . . C8 O26 C13 C21 -116.04(12) no . . . . C13 O26 C8 C9 -178.34(13) no . . . . C13 O26 C8 C13 0.00(6) no . . . . C13 O26 C8 C18 0.72(11) no . . . . C3 O27 C12 C13 -164.46(11) no . . . . C12 O27 C3 O28 -2.0(2) no . . . . C12 O27 C3 C2 177.08(11) no . . . . O4 N30 C6 C4 176.34(13) no . . . . O4 N30 C6 C11 -2.6(2) no . . . . O29 N30 C6 C4 -3.1(2) no . . . . O29 N30 C6 C11 177.99(13) no . . . . C3 C2 C5 C11 -178.62(13) no . . . . C5 C2 C3 O27 2.8(2) no . . . . C5 C2 C3 O28 -178.12(14) no . . . . C3 C2 C7 C4 178.15(12) no . . . . C7 C2 C3 O27 -175.37(13) no . . . . C7 C2 C3 O28 3.7(2) no . . . . C5 C2 C7 C4 -0.1(2) no . . . . C7 C2 C5 C11 -0.5(2) no . . . . C6 C4 C7 C2 0.4(2) no . . . . C7 C4 C6 N30 -179.10(13) no . . . . C7 C4 C6 C11 -0.2(2) no . . . . C2 C5 C11 C6 0.7(2) no . . . . N30 C6 C11 C5 178.58(12) no . . . . C4 C6 C11 C5 -0.3(2) no . . . . O26 C8 C9 C10 -4.3(2) no . . . . O26 C8 C9 C16 175.22(12) no . . . . O26 C8 C13 O26 0.00(6) no . . . . O26 C8 C13 C12 -86.94(14) no . . . . O26 C8 C13 C18 179.05(14) no . . . . O26 C8 C13 C21 86.23(14) no . . . . O26 C8 C18 C13 -0.71(11) no . . . . O26 C8 C18 C19 173.82(18) no . . . . C9 C8 C18 C13 177.9(2) no . . . . C9 C8 C18 C19 -7.6(4) no . . . . C18 C8 C9 C10 177.3(2) no . . . . C18 C8 C9 C16 -3.2(3) no . . . . C13 C8 C18 C13 0.00(6) no . . . . C13 C8 C18 C19 174.5(3) no . . . . C18 C8 C13 O26 -179.05(16) no . . . . C18 C8 C13 C12 94.01(16) no . . . . C18 C8 C13 C18 0.00(9) no . . . . C18 C8 C13 C21 -92.82(16) no . . . . C8 C9 C10 C14 179.40(13) no . . . . C8 C9 C16 C17 -179.47(14) no . . . . C10 C9 C16 C17 0.1(2) no . . . . C16 C9 C10 C14 -0.1(2) no . . . . C9 C10 C14 C15 -0.2(3) no . . . . O27 C12 C13 O26 59.22(15) no . . . . O27 C12 C13 C8 108.25(14) no . . . . O27 C12 C13 C18 157.26(11) no . . . . O27 C12 C13 C21 -65.40(16) no . . . . O26 C13 C18 C8 0.67(10) no . . . . O26 C13 C18 C19 -174.64(15) no . . . . O26 C13 C21 F3 53.72(17) no . . . . O26 C13 C21 F5 -68.15(17) no . . . . O26 C13 C21 F25 172.35(11) no . . . . C8 C13 C18 C8 0.00(7) no . . . . C8 C13 C18 C19 -175.3(2) no . . . . C8 C13 C21 F3 5.3(2) no . . . . C8 C13 C21 F5 -116.57(15) no . . . . C8 C13 C21 F25 123.93(14) no . . . . C12 C13 C18 C8 -111.59(14) no . . . . C12 C13 C18 C19 73.1(2) no . . . . C12 C13 C21 F3 179.05(13) no . . . . C12 C13 C21 F5 57.2(2) no . . . . C12 C13 C21 F25 -62.33(18) no . . . . C18 C13 C21 F3 -42.9(2) no . . . . C18 C13 C21 F5 -164.77(14) no . . . . C18 C13 C21 F25 75.73(18) no . . . . C21 C13 C18 C8 111.20(14) no . . . . C21 C13 C18 C19 -64.1(2) no . . . . C10 C14 C15 O2 -178.45(15) no . . . . C10 C14 C15 C17 0.6(3) no . . . . O2 C15 C17 C16 178.45(14) no . . . . C14 C15 C17 C16 -0.7(3) no . . . . C9 C16 C17 C15 0.3(3) no . . . . C8 C18 C19 F22 148.2(2) no . . . . C8 C18 C19 F23 -93.0(2) no . . . . C8 C18 C19 F24 27.4(3) no . . . . C13 C18 C19 F22 -39.1(2) no . . . . C13 C18 C19 F23 79.6(2) no . . . . C13 C18 C19 F24 -159.93(15) 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 F3 F23 3.245(2) no . . F3 O26 2.788(2) no . . F3 C8 3.117(2) no . . F3 C18 2.825(2) no . . F3 C19 3.555(3) no . . F5 O26 2.938(2) no . . F5 O27 2.699(2) no . . F5 C12 2.956(2) no . . F22 F25 3.281(2) no . . F22 C12 3.276(2) no . . F22 C13 3.060(2) no . . F23 F25 3.207(3) no . . F23 C8 3.393(2) no . . F23 C13 3.346(2) no . . F23 C21 3.449(3) no . . F24 C8 3.078(2) no . . F24 C9 3.599(3) no . . F24 C16 3.245(3) no . . F25 O27 3.551(2) no . . F25 C12 2.929(3) no . . F25 C18 3.056(2) no . . F25 C19 3.348(3) no . . O4 C4 3.556(3) no . . O4 C11 2.706(2) no . . O26 O27 2.804(2) no . . O26 C10 2.813(2) no . . O26 C19 3.522(2) no . . O27 C5 2.717(2) no . . O27 C21 2.963(2) no . . O28 C7 2.846(2) no . . O28 C12 2.631(2) no . . O29 C4 2.722(2) no . . O29 C11 3.548(3) no . . C2 C6 2.734(2) no . . C4 C5 2.794(3) no . . C7 C11 2.790(3) no . . C9 C15 2.789(3) no . . C10 C17 2.769(3) no . . C12 C19 3.475(3) no . . C14 C16 2.786(3) no . . C14 C20 2.793(3) no . . C16 C18 3.298(3) no . . C19 C21 3.391(3) no . . F3 F22 2.7501(19) no . 1_545 F3 C5 3.317(2) no . 3_655 F3 C11 3.174(3) no . 3_655 F5 F5 2.663(2) no . 3_655 F22 F3 2.7501(19) no . 1_565 F22 O26 3.335(2) no . 1_565 F22 C8 3.393(2) no . 1_565 F22 C9 3.487(2) no . 1_565 F22 C10 3.436(3) no . 1_565 F23 O2 3.122(2) no . 2_665 F23 C16 3.533(3) no . 2_655 F23 C17 3.409(3) no . 2_655 F23 C20 3.504(3) no . 2_665 F24 F24 2.603(2) no . 2_655 F24 C10 3.386(3) no . 1_565 F24 C14 3.505(3) no . 1_565 F25 O27 3.008(2) no . 3_665 F25 O28 3.508(2) no . 3_665 F25 C2 3.157(2) no . 3_665 F25 C3 2.966(2) no . 3_665 F25 C5 3.381(2) no . 3_665 O2 F23 3.122(2) no . 2_645 O2 O4 3.347(2) no . 4_555 O2 O29 3.277(2) no . 4_555 O2 N30 3.055(2) no . 4_555 O2 C6 3.351(2) no . 4_555 O4 O2 3.347(2) no . 4_554 O4 C4 3.383(3) no . 1_545 O4 C7 3.413(3) no . 1_545 O4 C20 3.298(3) no . 4_544 O26 F22 3.335(2) no . 1_545 O26 O29 3.181(2) no . 7_655 O27 F25 3.008(2) no . 3_665 O28 F25 3.508(2) no . 3_665 O28 N30 3.508(2) no . 7_655 O28 C5 3.456(3) no . 1_565 O28 C6 3.483(2) no . 7_655 O28 C7 3.257(2) no . 7_665 O28 C11 3.541(3) no . 1_565 O29 O2 3.277(2) no . 4_554 O29 O26 3.181(2) no . 7_655 O29 C8 3.169(2) no . 7_655 O29 C9 3.382(2) no . 7_655 O29 C12 3.400(3) no . 7_655 O29 C14 3.454(3) no . 7_645 O29 C20 3.290(3) no . 4_554 N30 O2 3.055(2) no . 4_554 N30 O28 3.508(2) no . 7_655 N30 C20 3.519(3) no . 4_554 C2 F25 3.157(2) no . 3_665 C2 C4 3.544(3) no . 7_655 C2 C7 3.477(2) no . 7_655 C3 F25 2.966(2) no . 3_665 C3 C4 3.457(3) no . 7_655 C3 C6 3.523(2) no . 7_655 C4 O4 3.383(3) no . 1_565 C4 C2 3.544(3) no . 7_655 C4 C3 3.457(3) no . 7_655 C5 F3 3.317(2) no . 3_655 C5 F25 3.381(2) no . 3_665 C5 O28 3.456(3) no . 1_545 C5 C7 3.575(3) no . 7_655 C6 O2 3.351(2) no . 4_554 C6 O28 3.483(2) no . 7_655 C6 C3 3.523(2) no . 7_655 C7 O4 3.413(3) no . 1_565 C7 O28 3.257(2) no . 7_665 C7 C2 3.477(2) no . 7_655 C7 C5 3.575(3) no . 7_655 C8 F22 3.393(2) no . 1_545 C8 O29 3.169(2) no . 7_655 C9 F22 3.487(2) no . 1_545 C9 O29 3.382(2) no . 7_655 C10 F22 3.436(3) no . 1_545 C10 F24 3.386(3) no . 1_545 C11 F3 3.174(3) no . 3_655 C11 O28 3.541(3) no . 1_545 C12 O29 3.400(3) no . 7_655 C14 F24 3.505(3) no . 1_545 C14 O29 3.454(3) no . 7_645 C14 C20 3.477(3) no . 6_655 C16 F23 3.533(3) no . 2_655 C17 F23 3.409(3) no . 2_655 C20 F23 3.504(3) no . 2_645 C20 O4 3.298(3) no . 4_545 C20 O29 3.290(3) no . 4_555 C20 N30 3.519(3) no . 4_555 C20 C14 3.477(3) no . 6_645 F5 H5 3.0505 no . . F5 H12A 3.1877 no . . F22 H12A 2.9456 no . . F22 H12B 3.3024 no . . F24 H16 2.4368 no . . F25 H12A 2.6277 no . . O2 H14 2.6493 no . . O2 H17 2.4853 no . . O4 H11 2.4106 no . . O26 H10 2.4553 no . . O26 H12A 3.3082 no . . O26 H12B 2.6756 no . . O27 H5 2.3951 no . . O28 H7 2.5561 no . . O28 H12A 2.7836 no . . O28 H12B 2.4351 no . . O29 H4 2.4358 no . . N30 H4 2.6298 no . . N30 H11 2.6072 no . . C2 H4 3.2678 no . . C2 H11 3.2680 no . . C3 H5 2.6880 no . . C3 H7 2.6065 no . . C3 H12A 2.7070 no . . C3 H12B 2.5059 no . . C4 H11 3.2857 no . . C5 H7 3.2740 no . . C6 H5 3.2377 no . . C6 H7 3.2362 no . . C7 H5 3.2747 no . . C8 H10 2.6011 no . . C8 H12B 3.0445 no . . C8 H16 2.6668 no . . C9 H14 3.2794 no . . C9 H17 3.2712 no . . C10 H16 3.2619 no . . C11 H4 3.2858 no . . C14 H17 3.2650 no . . C14 H20A 2.6842 no . . C14 H20C 2.7639 no . . C15 H10 3.2537 no . . C15 H16 3.2623 no . . C15 H20A 2.5983 no . . C15 H20B 3.1945 no . . C15 H20C 2.6355 no . . C16 H10 3.2606 no . . C17 H14 3.2686 no . . C18 H12A 2.9518 no . . C18 H12B 2.6530 no . . C18 H16 3.0817 no . . C19 H12A 3.4870 no . . C19 H12B 3.5128 no . . C19 H16 3.1993 no . . C20 H14 2.4914 no . . C21 H12A 2.7330 no . . C21 H12B 3.3965 no . . H4 H7 2.3432 no . . H5 H11 2.3472 no . . H10 H14 2.3395 no . . H14 H20A 2.2171 no . . H14 H20B 3.4601 no . . H14 H20C 2.3365 no . . H16 H17 2.3299 no . . F3 H5 2.9122 no . 3_655 F3 H11 2.6335 no . 3_655 F3 H17 3.4594 no . 2_655 F5 H5 3.1405 no . 3_655 F5 H12A 3.5528 no . 1_545 F5 H12A 2.9891 no . 3_665 F22 H10 3.2592 no . 1_565 F22 H17 3.5452 no . 2_665 F23 H16 2.9700 no . 2_655 F23 H17 2.7172 no . 2_655 F23 H20A 3.2303 no . 2_665 F23 H20B 3.5339 no . 2_665 F24 H16 2.8507 no . 2_655 F25 H5 3.3199 no . 3_665 F25 H11 3.2855 no . 3_655 F25 H12A 3.3801 no . 3_665 O4 H4 3.0982 no . 1_545 O4 H7 3.1404 no . 1_545 O4 H10 3.1913 no . 7_645 O4 H12B 3.5955 no . 7_655 O4 H14 3.1353 no . 7_645 O4 H17 3.3510 no . 4_554 O4 H20A 3.3150 no . 4_544 O4 H20B 2.4737 no . 4_544 O26 H4 2.9637 no . 7_655 O27 H4 3.3580 no . 7_655 O28 H4 3.4776 no . 7_665 O28 H5 3.1321 no . 1_565 O28 H7 2.4054 no . 7_665 O28 H11 3.3031 no . 1_565 O29 H10 3.1500 no . 7_645 O29 H12B 2.6023 no . 7_655 O29 H14 2.7072 no . 7_645 O29 H20B 3.0344 no . 4_554 O29 H20C 3.0677 no . 4_554 N30 H10 3.4725 no . 7_645 N30 H12B 3.0509 no . 7_655 N30 H14 3.2776 no . 7_645 N30 H20B 3.2698 no . 4_554 N30 H20C 3.5848 no . 4_554 C3 H4 3.5608 no . 7_655 C3 H7 3.4625 no . 7_665 C4 H20B 2.9723 no . 4_554 C5 H7 3.4499 no . 7_655 C6 H20B 3.2037 no . 4_554 C7 H11 3.2726 no . 1_565 C9 H20C 3.5851 no . 6_655 C10 H4 3.5328 no . 7_655 C10 H12B 3.5920 no . 1_545 C10 H20B 3.3247 no . 6_655 C10 H20C 3.1781 no . 6_655 C11 H7 3.2655 no . 1_545 C12 H10 3.5841 no . 1_565 C14 H20B 3.3299 no . 6_655 C14 H20C 2.9555 no . 6_655 C15 H20C 3.1645 no . 6_655 C16 H16 3.4382 no . 2_655 C16 H20A 3.1160 no . 1_565 C17 H20A 3.0544 no . 1_565 C17 H20C 3.5725 no . 6_655 C19 H16 3.4075 no . 2_655 C20 H14 3.5205 no . 6_645 C21 H5 3.4917 no . 3_655 C21 H11 3.4893 no . 3_655 H4 O4 3.0982 no . 1_565 H4 O26 2.9637 no . 7_655 H4 O27 3.3580 no . 7_655 H4 O28 3.4776 no . 7_665 H4 C3 3.5608 no . 7_655 H4 C10 3.5328 no . 7_655 H4 H10 2.9296 no . 7_655 H4 H12B 3.5376 no . 7_655 H4 H20B 2.7665 no . 4_554 H5 F3 2.9122 no . 3_655 H5 F5 3.1405 no . 3_655 H5 F25 3.3199 no . 3_665 H5 O28 3.1321 no . 1_545 H5 C21 3.4917 no . 3_655 H7 O4 3.1404 no . 1_565 H7 O28 2.4054 no . 7_665 H7 C3 3.4625 no . 7_665 H7 C5 3.4499 no . 7_655 H7 C11 3.2655 no . 1_565 H7 H7 2.9582 no . 7_665 H7 H11 2.8883 no . 1_565 H10 F22 3.2592 no . 1_545 H10 O4 3.1913 no . 7_645 H10 O29 3.1500 no . 7_645 H10 N30 3.4725 no . 7_645 H10 C12 3.5841 no . 1_545 H10 H4 2.9296 no . 7_655 H10 H12B 2.7472 no . 1_545 H10 H20B 3.2719 no . 6_655 H10 H20C 3.5675 no . 6_655 H11 F3 2.6335 no . 3_655 H11 F25 3.2855 no . 3_655 H11 O28 3.3031 no . 1_545 H11 C7 3.2726 no . 1_545 H11 C21 3.4893 no . 3_655 H11 H7 2.8883 no . 1_545 H11 H17 3.5974 no . 4_554 H12A F5 3.5528 no . 1_565 H12A F5 2.9891 no . 3_665 H12A F25 3.3801 no . 3_665 H12B O4 3.5955 no . 7_655 H12B O29 2.6023 no . 7_655 H12B N30 3.0509 no . 7_655 H12B C10 3.5920 no . 1_565 H12B H4 3.5376 no . 7_655 H12B H10 2.7472 no . 1_565 H14 O4 3.1353 no . 7_645 H14 O29 2.7072 no . 7_645 H14 N30 3.2776 no . 7_645 H14 C20 3.5205 no . 6_655 H14 H16 3.5817 no . 1_545 H14 H20A 3.4573 no . 6_655 H14 H20B 3.2887 no . 6_655 H14 H20C 3.2344 no . 6_655 H16 F23 2.9700 no . 2_655 H16 F24 2.8507 no . 2_655 H16 C16 3.4382 no . 2_655 H16 C19 3.4075 no . 2_655 H16 H14 3.5817 no . 1_565 H16 H16 2.8024 no . 2_655 H16 H20A 3.1068 no . 1_565 H17 F3 3.4594 no . 2_655 H17 F22 3.5452 no . 2_645 H17 F23 2.7172 no . 2_655 H17 O4 3.3510 no . 4_555 H17 H11 3.5974 no . 4_555 H17 H20A 3.0066 no . 1_565 H20A F23 3.2303 no . 2_645 H20A O4 3.3150 no . 4_545 H20A C16 3.1160 no . 1_545 H20A C17 3.0544 no . 1_545 H20A H14 3.4573 no . 6_645 H20A H16 3.1068 no . 1_545 H20A H17 3.0066 no . 1_545 H20A H20C 3.1238 no . 6_645 H20B F23 3.5339 no . 2_645 H20B O4 2.4737 no . 4_545 H20B O29 3.0344 no . 4_555 H20B N30 3.2698 no . 4_555 H20B C4 2.9723 no . 4_555 H20B C6 3.2037 no . 4_555 H20B C10 3.3247 no . 6_645 H20B C14 3.3299 no . 6_645 H20B H4 2.7665 no . 4_555 H20B H10 3.2719 no . 6_645 H20B H14 3.2887 no . 6_645 H20C O29 3.0677 no . 4_555 H20C N30 3.5848 no . 4_555 H20C C9 3.5851 no . 6_645 H20C C10 3.1781 no . 6_645 H20C C14 2.9555 no . 6_645 H20C C15 3.1645 no . 6_645 H20C C17 3.5725 no . 6_645 H20C H10 3.5675 no . 6_645 H20C H14 3.2344 no . 6_645 H20C H20A 3.1238 no . 6_655 H20C H20C 3.5211 no . 6_645 H20C H20C 3.5211 no . 6_655 #============================================================================== #============================================================================== # 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 948160' ####################################################################### # # 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_SX030 #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C19 H14 F3 N O5' _chemical_formula_moiety 'C19 H14 F3 N O5' _chemical_formula_weight 393.32 _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 5.877(4) _cell_length_b 11.649(8) _cell_length_c 12.864(8) _cell_angle_alpha 87.422(12) _cell_angle_beta 81.769(12) _cell_angle_gamma 83.004(14) _cell_volume 864.8(10) _cell_formula_units_Z 2 _cell_measurement_reflns_used 2387 _cell_measurement_theta_min 3.20 _cell_measurement_theta_max 27.50 _cell_measurement_temperature 93 #------------------------------------------------------------------------------ _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.240 _exptl_crystal_size_mid 0.140 _exptl_crystal_size_min 0.140 _exptl_crystal_density_diffrn 1.510 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 404.00 _exptl_absorpt_coefficient_mu 0.130 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'REQAB (Rigaku, 1998)' _exptl_absorpt_correction_T_min 0.877 _exptl_absorpt_correction_T_max 0.982 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 93 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_measurement_device_type 'Rigaku XtaLAB mini' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 6.827 _diffrn_reflns_number 9140 _diffrn_reflns_av_R_equivalents 0.0312 _diffrn_reflns_theta_max 27.45 _diffrn_reflns_theta_min 3.20 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _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 3934 _reflns_number_gt 3422 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0401 _refine_ls_wR_factor_ref 0.1097 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 3934 _refine_ls_number_parameters 254 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0543P)^2^+0.2995P] 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 0.40 _refine_diff_density_min -0.25 _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 0.0033 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 0.06111(15) 0.08047(7) 0.87773(8) 0.0326(2) Uani 1 2 d . . . F2 F -0.19434(15) 0.15228(8) 1.00072(6) 0.0281(2) Uani 1 2 d . . . F3 F -0.20110(16) 0.21462(8) 0.84124(7) 0.0337(2) Uani 1 2 d . . . O4 O 0.41508(15) 0.40979(8) 0.65162(7) 0.0189(2) Uani 1 2 d . . . O5 O -0.53328(16) 0.82537(9) 0.51966(8) 0.0228(2) Uani 1 2 d . . . O6 O -0.23941(17) 0.84133(9) 0.39906(7) 0.0224(2) Uani 1 2 d . . . O7 O -0.21849(16) 0.34229(8) 1.14902(7) 0.0198(2) Uani 1 2 d . . . O8 O 0.10430(15) 0.39897(8) 0.77492(7) 0.0155(2) Uani 1 2 d . . . N9 N -0.33129(18) 0.79843(9) 0.48135(8) 0.0157(2) Uani 1 2 d . . . C10 C 0.0669(2) 0.18853(10) 1.18645(9) 0.0137(2) Uani 1 2 d . . . C11 C 0.2174(2) 0.44375(10) 0.68683(9) 0.0136(2) Uani 1 2 d . . . C12 C 0.0703(2) 0.53864(10) 0.63720(9) 0.0130(2) Uani 1 2 d . . . C13 C -0.1904(2) 0.70862(10) 0.53677(9) 0.0138(2) Uani 1 2 d . . . C14 C 0.0409(2) 0.68140(11) 0.49626(9) 0.0146(2) Uani 1 2 d . . . C15 C -0.1634(2) 0.56772(11) 0.67605(9) 0.0139(2) Uani 1 2 d . . . C16 C -0.0656(2) 0.15268(11) 1.27856(10) 0.0154(2) Uani 1 2 d . . . C17 C -0.0349(2) 0.28391(11) 1.12057(9) 0.0138(2) Uani 1 2 d . . . C18 C -0.2958(2) 0.65409(11) 0.62616(9) 0.0148(2) Uani 1 2 d . . . C19 C 0.2385(2) 0.30302(11) 0.82366(9) 0.0162(2) Uani 1 2 d . . . C20 C 0.1075(2) 0.31604(11) 1.01725(9) 0.0144(2) Uani 1 2 d . . . C21 C 0.0960(2) 0.26965(11) 0.92528(9) 0.0143(2) Uani 1 2 d . . . C22 C 0.0276(2) 0.06652(11) 1.34358(10) 0.0194(3) Uani 1 2 d . . . C23 C -0.0592(2) 0.17967(11) 0.91267(10) 0.0169(3) Uani 1 2 d . . . C24 C 0.3874(2) 0.05103(12) 1.22586(11) 0.0222(3) Uani 1 2 d . . . C25 C 0.2549(3) 0.01632(11) 1.31741(11) 0.0219(3) Uani 1 2 d . . . C26 C 0.2939(2) 0.13605(11) 1.15960(10) 0.0183(3) Uani 1 2 d . . . C27 C 0.1716(2) 0.59568(10) 0.54783(9) 0.0139(2) Uani 1 2 d . . . C28 C 0.2572(2) 0.40948(11) 1.03031(10) 0.0189(3) Uani 1 2 d . . . H14 H 0.10775 0.7203 0.43504 0.0175 Uiso 1 2 calc R . . H15 H -0.23154 0.52827 0.73666 0.0167 Uiso 1 2 calc R . . H16 H -0.22019 0.18747 1.29677 0.0185 Uiso 1 2 calc R . . H18 H -0.45409 0.67544 0.65232 0.0177 Uiso 1 2 calc R . . H19A H 0.38702 0.32674 0.83775 0.0195 Uiso 1 2 calc R . . H19B H 0.27239 0.2365 0.77638 0.0195 Uiso 1 2 calc R . . H22 H -0.06354 0.0419 1.40573 0.0232 Uiso 1 2 calc R . . H24 H 0.54253 0.01659 1.20842 0.0266 Uiso 1 2 calc R . . H25 H 0.31951 -0.04186 1.36233 0.0263 Uiso 1 2 calc R . . H26 H 0.38388 0.15847 1.09627 0.0219 Uiso 1 2 calc R . . H27 H 0.33072 0.57573 0.5222 0.0167 Uiso 1 2 calc R . . H28A H 0.3119 0.44265 0.9612 0.0227 Uiso 1 2 calc R . . H28B H 0.39037 0.37615 1.06412 0.0227 Uiso 1 2 calc R . . H28C H 0.16662 0.47028 1.07407 0.0227 Uiso 1 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 0.0273(5) 0.0198(4) 0.0483(6) -0.0010(4) 0.0046(4) -0.0129(4) F2 0.0295(5) 0.0346(5) 0.0217(4) -0.0182(4) 0.0049(3) -0.0041(3) F3 0.0350(5) 0.0344(5) 0.0383(5) -0.0108(4) -0.0239(4) 0.0077(4) O4 0.0142(4) 0.0230(5) 0.0178(4) 0.0006(4) 0.0007(3) 0.0033(4) O5 0.0165(5) 0.0264(5) 0.0231(5) 0.0032(4) -0.0013(4) 0.0043(4) O6 0.0238(5) 0.0236(5) 0.0187(5) -0.0036(4) -0.0012(4) 0.0081(4) O7 0.0176(5) 0.0216(5) 0.0179(5) 0.0039(4) -0.0010(4) 0.0013(4) O8 0.0146(4) 0.0183(5) 0.0118(4) 0.0015(3) -0.0002(3) 0.0041(3) N9 0.0175(5) 0.0152(5) 0.0151(5) -0.0023(4) -0.0041(4) 0.0004(4) C10 0.0152(6) 0.0130(6) 0.0133(6) -0.0019(5) -0.0034(4) -0.0009(4) C11 0.0149(6) 0.0155(6) 0.0113(5) -0.0038(5) -0.0026(4) -0.0014(4) C12 0.0149(6) 0.0134(6) 0.0114(6) -0.0021(4) -0.0034(4) -0.0021(4) C13 0.0170(6) 0.0127(6) 0.0125(6) -0.0017(5) -0.0049(4) -0.0012(4) C14 0.0168(6) 0.0153(6) 0.0123(6) -0.0044(5) -0.0018(4) 0.0001(4) C15 0.0152(6) 0.0165(6) 0.0104(5) -0.0042(5) -0.0007(4) -0.0008(4) C16 0.0168(6) 0.0148(6) 0.0148(6) -0.0022(5) -0.0019(5) -0.0018(4) C17 0.0140(6) 0.0157(6) 0.0122(6) -0.0028(5) -0.0022(4) -0.0016(4) C18 0.0130(6) 0.0173(6) 0.0142(6) -0.0023(5) -0.0016(4) -0.0021(5) C19 0.0151(6) 0.0185(6) 0.0133(6) 0.0025(5) -0.0012(4) 0.0032(5) C20 0.0122(5) 0.0148(6) 0.0153(6) 0.0006(4) -0.0014(4) 0.0022(4) C21 0.0124(5) 0.0151(6) 0.0142(6) 0.0016(4) -0.0011(4) 0.0024(4) C22 0.0266(7) 0.0175(6) 0.0146(6) -0.0059(5) -0.0027(5) 0.0021(5) C23 0.0164(6) 0.0188(6) 0.0149(6) 0.0003(5) -0.0018(5) -0.0017(5) C24 0.0169(6) 0.0206(7) 0.0285(7) 0.0030(5) -0.0057(5) -0.0011(5) C25 0.0282(7) 0.0154(6) 0.0236(7) -0.0001(5) -0.0118(6) 0.0031(5) C26 0.0159(6) 0.0197(6) 0.0183(6) -0.0008(5) -0.0011(5) 0.0013(5) C27 0.0132(5) 0.0154(6) 0.0134(6) -0.0029(5) -0.0008(4) -0.0025(4) C28 0.0209(6) 0.0198(6) 0.0170(6) -0.0059(5) -0.0036(5) 0.0016(5) #============================================================================== _computing_data_collection 'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)' _computing_cell_refinement 'CrystalClear-SM Expert 2.0 r4' _computing_data_reduction 'CrystalClear-SM Expert 2.0 r4' _computing_structure_solution 'Il Milione (Burla, et al., 2007)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2011)' _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 1.3394(16) yes . . F2 C23 1.3369(16) yes . . F3 C23 1.3448(18) yes . . O4 C11 1.2101(16) yes . . O5 N9 1.2273(15) yes . . O6 N9 1.2314(15) yes . . O7 C17 1.2210(16) yes . . O8 C11 1.3468(15) yes . . O8 C19 1.4587(16) yes . . N9 C13 1.4762(17) yes . . C10 C16 1.3982(18) yes . . C10 C17 1.4863(18) yes . . C10 C26 1.4008(19) yes . . C11 C12 1.4962(18) yes . . C12 C15 1.3989(18) yes . . C12 C27 1.3962(17) yes . . C13 C14 1.3882(18) yes . . C13 C18 1.3912(17) yes . . C14 C27 1.3882(18) yes . . C15 C18 1.3869(18) yes . . C16 C22 1.3887(19) yes . . C17 C20 1.5233(17) yes . . C19 C21 1.5103(17) yes . . C20 C21 1.3362(19) yes . . C20 C28 1.510(2) yes . . C21 C23 1.499(2) yes . . C22 C25 1.392(2) yes . . C24 C25 1.389(2) yes . . C24 C26 1.391(2) yes . . 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 C11 O8 C19 114.23(9) yes . . . O5 N9 O6 123.92(11) yes . . . O5 N9 C13 118.08(10) yes . . . O6 N9 C13 118.00(10) yes . . . C16 C10 C17 119.06(11) yes . . . C16 C10 C26 119.48(11) yes . . . C17 C10 C26 121.44(11) yes . . . O4 C11 O8 123.48(11) yes . . . O4 C11 C12 124.12(11) yes . . . O8 C11 C12 112.40(10) yes . . . C11 C12 C15 121.74(11) yes . . . C11 C12 C27 117.84(11) yes . . . C15 C12 C27 120.38(11) yes . . . N9 C13 C14 118.31(10) yes . . . N9 C13 C18 118.67(11) yes . . . C14 C13 C18 123.02(11) yes . . . C13 C14 C27 118.05(11) yes . . . C12 C15 C18 120.05(11) yes . . . C10 C16 C22 120.38(12) yes . . . O7 C17 C10 122.96(11) yes . . . O7 C17 C20 118.94(11) yes . . . C10 C17 C20 117.89(10) yes . . . C13 C18 C15 118.21(11) yes . . . O8 C19 C21 107.61(10) yes . . . C17 C20 C21 124.03(13) yes . . . C17 C20 C28 112.02(11) yes . . . C21 C20 C28 123.92(11) yes . . . C19 C21 C20 123.16(12) yes . . . C19 C21 C23 113.39(11) yes . . . C20 C21 C23 123.45(11) yes . . . C16 C22 C25 119.81(12) yes . . . F1 C23 F2 106.36(11) yes . . . F1 C23 F3 105.93(11) yes . . . F1 C23 C21 111.91(11) yes . . . F2 C23 F3 106.55(11) yes . . . F2 C23 C21 114.51(11) yes . . . F3 C23 C21 111.04(11) yes . . . C25 C24 C26 120.23(12) yes . . . C22 C25 C24 120.22(12) yes . . . C10 C26 C24 119.86(11) yes . . . C12 C27 C14 120.28(11) yes . . . #============================================================================== #============================================================================== # 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 948161' ####################################################################### # # 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_SX032 #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C20 H13 F6 N O6' _chemical_formula_moiety 'C20 H13 F6 N O6' _chemical_formula_weight 477.32 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,1/2+Y,1/2-Z 3 -X,-Y,-Z 4 +X,1/2-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 10.5731(7) _cell_length_b 28.9962(19) _cell_length_c 13.1962(9) _cell_angle_alpha 90.0000 _cell_angle_beta 94.339(4) _cell_angle_gamma 90.0000 _cell_volume 4034.1(5) _cell_formula_units_Z 8 _cell_measurement_reflns_used 7856 _cell_measurement_theta_min 2.60 _cell_measurement_theta_max 27.50 _cell_measurement_temperature 93 #------------------------------------------------------------------------------ _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.260 _exptl_crystal_size_mid 0.090 _exptl_crystal_size_min 0.090 _exptl_crystal_density_diffrn 1.572 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1936.00 _exptl_absorpt_coefficient_mu 0.151 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'REQAB (Rigaku, 1998)' _exptl_absorpt_correction_T_min 0.875 _exptl_absorpt_correction_T_max 0.987 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 93 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_measurement_device_type 'Rigaku XtaLAB mini' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 6.827 _diffrn_reflns_number 28233 _diffrn_reflns_av_R_equivalents 0.0547 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -36 _diffrn_reflns_limit_k_max 37 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _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 9229 _reflns_number_gt 6112 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0590 _refine_ls_wR_factor_ref 0.1363 _refine_ls_number_restraints 2 _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 9229 _refine_ls_number_parameters 635 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0437P)^2^+2.9187P] 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 0.56 _refine_diff_density_min -0.56 _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 0.0033 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 1.06455(14) 0.10131(5) 0.56651(11) 0.0319(3) Uani 1 4 d . . . F2 F 1.08970(15) -0.03213(5) 0.84560(11) 0.0371(4) Uani 1 4 d . . . F3 F 0.72300(16) 0.04181(6) 0.97438(13) 0.0484(4) Uani 1 4 d . . . F4 F 1.18786(14) 0.04437(5) 0.53774(12) 0.0362(4) Uani 1 4 d . . . F5 F 0.63704(15) -0.01477(5) 0.63045(12) 0.0416(4) Uani 1 4 d . . . F6 F 0.58080(17) 0.09371(7) 0.95117(14) 0.0641(6) Uani 1 4 d . . . F7 F 1.1104(2) 0.03234(7) 0.91966(17) 0.0741(7) Uani 1 4 d . . . F8 F 0.7656(2) 0.10467(8) 0.90498(16) 0.0751(6) Uani 1 4 d . . . F9 F 0.45565(17) 0.01700(9) 0.62933(14) 0.0718(7) Uani 1 4 d . . . F10 F 0.6056(3) 0.05114(7) 0.5668(2) 0.0987(10) Uani 1 4 d . . . F11 F 0.93055(17) 0.01275(7) 0.85296(13) 0.0547(5) Uani 1 4 d . . . F12 F 1.26188(16) 0.10418(6) 0.61476(14) 0.0505(5) Uani 1 4 d . . . O13 O 1.3671(2) -0.25960(7) 0.60570(16) 0.0524(6) Uani 1 4 d . . . O14 O 1.01242(19) -0.24527(7) 0.83849(16) 0.0440(5) Uani 1 4 d . . . O15 O 0.83015(16) 0.08846(6) 0.68988(15) 0.0341(4) Uani 1 4 d . . . O16 O 1.11603(17) -0.19562(7) 0.93527(16) 0.0456(5) Uani 1 4 d . . . O17 O 0.51688(18) -0.08925(6) 0.76635(17) 0.0441(5) Uani 1 4 d . . . O18 O 1.5125(2) -0.20753(8) 0.59183(18) 0.0564(6) Uani 1 4 d . . . O19 O 0.49554(17) 0.27150(6) 0.64322(14) 0.0336(4) Uani 1 4 d . . . O20 O 1.10206(17) 0.25717(6) 0.94049(15) 0.0363(4) Uani 1 4 d . . . O21 O 1.33981(16) 0.06424(6) 0.82400(15) 0.0386(5) Uani 1 4 d . . . O22 O 1.07193(15) -0.03647(5) 0.61750(13) 0.0272(4) Uani 1 4 d . . . O23 O 0.92863(16) -0.08714(6) 0.67144(14) 0.0350(4) Uani 1 4 d . . . O24 O 0.64072(16) -0.03862(5) 0.85772(13) 0.0286(4) Uani 1 4 d . . . N25 N 1.4024(3) -0.21929(9) 0.60195(17) 0.0421(6) Uani 1 4 d . . . N26 N 1.0233(2) -0.20734(7) 0.87936(17) 0.0329(5) Uani 1 4 d . . . C27 C 0.6640(2) 0.14360(8) 0.69249(19) 0.0252(5) Uani 1 4 d . . . C28 C 0.7241(2) -0.11248(8) 0.83129(18) 0.0237(5) Uani 1 4 d . . . C29 C 0.5561(2) 0.23038(8) 0.65705(18) 0.0249(5) Uani 1 4 d . . . C30 C 1.1302(2) -0.11478(8) 0.62767(18) 0.0247(5) Uani 1 4 d . . . C31 C 1.0504(2) 0.18920(8) 0.85316(19) 0.0283(5) Uani 1 4 d . . . C32 C 1.1626(3) 0.07616(8) 0.60596(19) 0.0298(6) Uani 1 4 d . . . C33 C 1.0312(2) -0.07907(8) 0.64209(18) 0.0269(5) Uani 1 4 d . . . C34 C 1.1839(3) -0.19539(9) 0.62473(19) 0.0353(6) Uani 1 4 d . . . C35 C 1.3438(3) -0.13729(9) 0.6026(2) 0.0352(6) Uani 1 4 d . . . C36 C 0.6833(2) 0.22313(8) 0.64046(17) 0.0234(5) Uani 1 4 d . . . C37 C 1.2378(2) 0.08265(9) 0.8031(2) 0.0344(6) Uani 1 4 d . . . C38 C 0.9941(2) 0.00225(8) 0.6446(2) 0.0303(6) Uani 1 4 d . . . C39 C 0.9187(2) -0.17397(8) 0.86142(19) 0.0264(5) Uani 1 4 d . . . C40 C 1.0804(2) 0.14608(8) 0.81801(19) 0.0269(5) Uani 1 4 d . . . C41 C 1.1427(2) 0.21552(8) 0.90815(18) 0.0252(5) Uani 1 4 d . . . C42 C 0.9306(2) -0.13143(8) 0.90782(19) 0.0273(5) Uani 1 4 d . . . C43 C 0.5364(2) 0.15141(8) 0.7089(2) 0.0287(5) Uani 1 4 d . . . C44 C 0.7356(2) 0.17995(8) 0.65782(18) 0.0236(5) Uani 1 4 d . . . C45 C 0.6155(2) -0.07990(8) 0.8135(2) 0.0277(5) Uani 1 4 d . . . C46 C 0.7231(2) 0.09836(9) 0.7098(2) 0.0329(6) Uani 1 4 d . . . C47 C 0.8317(2) -0.10047(8) 0.89267(18) 0.0255(5) Uani 1 4 d . . . C48 C 0.4826(2) 0.19429(9) 0.6916(2) 0.0290(5) Uani 1 4 d . . . C49 C 1.2028(2) 0.12843(8) 0.83872(18) 0.0238(5) Uani 1 4 d . . . C50 C 0.5683(3) 0.31015(8) 0.6107(2) 0.0324(6) Uani 1 4 d . . . C51 C 1.0548(3) 0.01163(9) 0.8410(2) 0.0353(6) Uani 1 4 d . . . C52 C 1.3070(3) -0.18259(9) 0.60987(18) 0.0302(6) Uani 1 4 d . . . C53 C 1.2542(2) -0.10298(9) 0.6114(2) 0.0322(6) Uani 1 4 d . . . C54 C 1.2938(2) 0.15506(8) 0.89382(18) 0.0252(5) Uani 1 4 d . . . C55 C 1.0956(3) -0.16080(8) 0.6342(2) 0.0316(6) Uani 1 4 d . . . C56 C 1.1914(3) 0.28551(9) 1.0005(2) 0.0414(7) Uani 1 4 d . . . C57 C 1.0679(3) 0.02722(12) 0.7309(3) 0.0220(11) Uani 0.703(9) 4 d . . . C58 C 0.5453(2) -0.00285(8) 0.8405(2) 0.0304(6) Uani 1 4 d . . . C59 C 1.1506(3) 0.06057(12) 0.7159(3) 0.0212(11) Uani 0.703(9) 4 d . . . C60 C 0.6761(3) 0.07309(12) 0.9109(2) 0.0456(8) Uani 1 4 d . . . C61 C 0.5788(3) 0.02467(10) 0.6423(2) 0.0439(8) Uani 1 4 d . . . C62 C 1.2651(2) 0.19866(8) 0.92762(18) 0.0246(5) Uani 1 4 d . . . C63 C 0.8135(2) -0.18691(8) 0.79940(18) 0.0269(5) Uani 1 4 d . . . C64 C 0.7150(2) -0.15568(8) 0.78437(19) 0.0262(5) Uani 1 4 d . . . C65 C 0.6385(4) 0.05577(16) 0.7281(4) 0.0246(14) Uani 0.581(10) 4 d . . . C66 C 0.6184(4) 0.04200(18) 0.8206(4) 0.0247(14) Uani 0.581(10) 4 d . . . H31 H 0.96699 0.20103 0.84 0.0340 Uiso 1 4 calc R . . H34 H 1.16065 -0.22697 0.62835 0.0423 Uiso 1 4 calc R . . H35 H 1.42913 -0.12967 0.59178 0.0423 Uiso 1 4 calc R . . H36 H 0.73338 0.24765 0.61744 0.0281 Uiso 1 4 calc R . . H38A H 0.91184 -0.00878 0.66649 0.0363 Uiso 1 4 calc R . . H38B H 0.97753 0.0231 0.5857 0.0363 Uiso 1 4 calc R . . H40 H 1.0181 0.12837 0.77976 0.0323 Uiso 1 4 calc R . . H42 H 1.00499 -0.12361 0.94917 0.0327 Uiso 1 4 calc R . . H43 H 0.48639 0.12693 0.73219 0.0344 Uiso 1 4 calc R . . H44 H 0.82206 0.1749 0.64593 0.0283 Uiso 1 4 calc R . . H47 H 0.83727 -0.071 0.92415 0.0306 Uiso 1 4 calc R . . H48 H 0.39605 0.19932 0.70308 0.0348 Uiso 1 4 calc R . . H50A H 0.60051 0.30318 0.54471 0.0389 Uiso 1 4 calc R . . H50B H 0.63963 0.31596 0.66084 0.0389 Uiso 1 4 calc R . . H50C H 0.51399 0.33756 0.60445 0.0389 Uiso 1 4 calc R . . H53 H 1.27757 -0.07148 0.60638 0.0387 Uiso 1 4 calc R . . H54 H 1.37681 0.14305 0.90834 0.0302 Uiso 1 4 calc R . . H55 H 1.01044 -0.16859 0.64521 0.0379 Uiso 1 4 calc R . . H56A H 1.26007 0.29487 0.95905 0.0496 Uiso 1 4 calc R . . H56B H 1.22667 0.26792 1.05944 0.0496 Uiso 1 4 calc R . . H56C H 1.14807 0.31299 1.02378 0.0496 Uiso 1 4 calc R . . H58A H 0.49597 0.0007 0.9009 0.0364 Uiso 1 4 calc R . . H58B H 0.4862 -0.01061 0.78121 0.0364 Uiso 1 4 calc R . . H62 H 1.32828 0.21686 0.96368 0.0295 Uiso 1 4 calc R . . H63 H 0.80902 -0.2164 0.76798 0.0323 Uiso 1 4 calc R . . H64 H 0.64128 -0.16358 0.74227 0.0314 Uiso 1 4 calc R . . C59B C 1.1266(8) 0.0464(3) 0.7759(7) 0.018(2) Uani 0.297(9) 4 d . . . C57B C 1.0955(8) 0.0424(3) 0.6762(6) 0.014(2) Uani 0.297(9) 4 d . . . C65B C 0.6610(5) 0.0682(2) 0.7925(5) 0.0195(19) Uani 0.419(10) 4 d . . . C66B C 0.5929(6) 0.0308(2) 0.7635(6) 0.0202(18) Uani 0.419(10) 4 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 F1 0.0348(8) 0.0279(8) 0.0332(8) 0.0046(6) 0.0036(7) 0.0033(6) F2 0.0460(9) 0.0253(8) 0.0386(9) 0.0035(7) -0.0051(7) -0.0008(6) F3 0.0510(10) 0.0396(9) 0.0521(11) 0.0126(8) -0.0122(8) -0.0015(8) F4 0.0327(8) 0.0311(8) 0.0454(9) 0.0002(7) 0.0080(7) -0.0136(7) F5 0.0501(10) 0.0289(8) 0.0456(10) 0.0080(7) 0.0022(8) -0.0077(7) F6 0.0514(11) 0.0816(14) 0.0558(12) 0.0391(10) -0.0197(9) -0.0396(10) F7 0.0865(15) 0.0562(12) 0.0814(15) -0.0343(11) 0.0180(12) -0.0393(11) F8 0.1054(18) 0.0637(14) 0.0584(13) 0.0055(13) 0.0210(13) 0.0159(11) F9 0.0397(10) 0.132(2) 0.0417(11) 0.0232(12) -0.0116(9) -0.0212(11) F10 0.118(2) 0.0479(12) 0.118(2) -0.0418(13) -0.0676(17) 0.0411(13) F11 0.0476(10) 0.0726(13) 0.0462(11) 0.0216(9) 0.0198(8) 0.0159(9) F12 0.0444(10) 0.0426(10) 0.0617(12) -0.0028(8) -0.0153(9) -0.0164(8) O13 0.0875(17) 0.0319(12) 0.0369(12) 0.0229(11) -0.0022(11) 0.0024(9) O14 0.0402(11) 0.0316(11) 0.0592(13) 0.0099(9) -0.0018(10) -0.0162(9) O15 0.0222(9) 0.0290(10) 0.0513(12) 0.0044(7) 0.0044(8) 0.0030(8) O16 0.0279(10) 0.0458(12) 0.0611(14) 0.0116(9) -0.0091(10) -0.0140(10) O17 0.0314(10) 0.0282(10) 0.0698(14) 0.0005(8) -0.0146(10) 0.0026(9) O18 0.0450(13) 0.0641(15) 0.0585(15) 0.0252(12) -0.0066(11) -0.0164(12) O19 0.0352(10) 0.0212(9) 0.0458(11) 0.0065(8) 0.0132(9) 0.0091(8) O20 0.0384(10) 0.0206(9) 0.0484(12) 0.0050(8) -0.0055(9) -0.0149(8) O21 0.0250(9) 0.0311(10) 0.0577(13) 0.0082(8) -0.0089(9) -0.0126(9) O22 0.0253(9) 0.0191(8) 0.0373(10) 0.0002(7) 0.0031(7) -0.0092(7) O23 0.0263(10) 0.0382(11) 0.0413(11) -0.0033(8) 0.0084(8) -0.0090(8) O24 0.0281(9) 0.0182(8) 0.0385(10) 0.0053(7) -0.0031(8) 0.0041(7) N25 0.0589(17) 0.0432(15) 0.0227(12) 0.0215(13) -0.0068(11) -0.0043(10) N26 0.0292(12) 0.0305(12) 0.0394(13) 0.0063(9) 0.0045(10) -0.0056(10) C27 0.0212(11) 0.0231(12) 0.0309(13) 0.0004(10) -0.0003(10) 0.0032(10) C28 0.0236(12) 0.0211(12) 0.0267(12) -0.0004(9) 0.0037(10) 0.0038(9) C29 0.0289(12) 0.0217(12) 0.0241(12) 0.0038(10) 0.0015(10) 0.0027(9) C30 0.0268(12) 0.0262(12) 0.0211(12) -0.0005(10) 0.0015(10) -0.0056(10) C31 0.0248(12) 0.0246(13) 0.0345(14) 0.0056(10) -0.0048(11) -0.0044(10) C32 0.0350(14) 0.0238(13) 0.0313(14) 0.0074(11) 0.0077(11) 0.0029(10) C33 0.0257(13) 0.0272(13) 0.0273(13) -0.0030(10) -0.0014(10) -0.0095(10) C34 0.0540(18) 0.0254(13) 0.0271(13) -0.0001(12) 0.0083(12) 0.0015(11) C35 0.0283(13) 0.0372(15) 0.0395(16) 0.0027(11) -0.0017(12) -0.0121(12) C36 0.0246(12) 0.0221(12) 0.0234(12) -0.0031(10) 0.0017(10) 0.0017(9) C37 0.0234(13) 0.0264(13) 0.0520(17) 0.0028(11) -0.0066(12) -0.0128(12) C38 0.0227(12) 0.0234(13) 0.0435(15) 0.0035(10) -0.0056(11) -0.0154(11) C39 0.0240(12) 0.0244(12) 0.0315(13) 0.0032(10) 0.0066(10) 0.0010(10) C40 0.0225(12) 0.0242(12) 0.0329(13) 0.0017(10) -0.0047(10) -0.0074(10) C41 0.0311(13) 0.0155(11) 0.0290(13) 0.0013(10) 0.0023(10) -0.0030(9) C42 0.0240(12) 0.0282(13) 0.0293(13) -0.0006(10) 0.0005(10) -0.0016(10) C43 0.0210(12) 0.0246(13) 0.0405(15) 0.0001(10) 0.0025(11) 0.0082(11) C44 0.0200(11) 0.0240(12) 0.0263(12) -0.0005(9) -0.0008(10) 0.0007(10) C45 0.0271(13) 0.0214(12) 0.0345(14) -0.0005(10) 0.0021(11) 0.0062(10) C46 0.0216(12) 0.0264(13) 0.0506(17) -0.0003(10) 0.0024(12) 0.0093(12) C47 0.0266(12) 0.0195(12) 0.0305(13) -0.0008(10) 0.0020(10) -0.0012(9) C48 0.0206(12) 0.0291(13) 0.0379(14) 0.0034(10) 0.0068(11) 0.0083(11) C49 0.0219(11) 0.0219(12) 0.0272(13) -0.0014(9) -0.0016(10) -0.0036(9) C50 0.0419(15) 0.0190(12) 0.0373(14) 0.0028(11) 0.0104(12) 0.0050(10) C51 0.0433(16) 0.0240(13) 0.0404(16) 0.0045(12) 0.0145(13) 0.0070(11) C52 0.0379(14) 0.0286(13) 0.0230(12) 0.0122(11) -0.0039(11) -0.0046(10) C53 0.0291(13) 0.0227(13) 0.0448(16) -0.0017(11) 0.0022(12) -0.0078(11) C54 0.0205(11) 0.0235(12) 0.0313(13) 0.0004(10) 0.0003(10) -0.0022(10) C55 0.0374(14) 0.0250(13) 0.0331(14) -0.0033(11) 0.0083(12) -0.0006(11) C56 0.0447(16) 0.0234(14) 0.0550(18) -0.0033(12) -0.0031(14) -0.0164(13) C57 0.0204(18) 0.0164(18) 0.029(2) 0.0029(15) 0.0015(17) -0.0040(17) C58 0.0270(13) 0.0242(13) 0.0404(15) 0.0086(10) 0.0061(11) 0.0100(11) C59 0.0156(18) 0.0164(18) 0.032(2) 0.0032(15) 0.0021(17) -0.0064(17) C60 0.0484(18) 0.056(2) 0.0295(15) 0.0291(16) -0.0132(14) -0.0110(14) C61 0.0493(18) 0.0395(17) 0.0400(16) 0.0160(14) -0.0153(14) -0.0175(13) C62 0.0251(12) 0.0207(12) 0.0278(13) -0.0066(10) 0.0006(10) -0.0028(10) C63 0.0298(13) 0.0225(12) 0.0287(13) 0.0006(10) 0.0038(10) -0.0036(10) C64 0.0266(12) 0.0249(12) 0.0270(13) -0.0035(10) 0.0020(10) 0.0036(10) C65 0.020(2) 0.022(2) 0.031(3) 0.0045(18) 0.000(2) -0.002(2) C66 0.025(2) 0.020(3) 0.027(3) 0.009(2) -0.005(2) -0.001(2) C59B 0.020(4) 0.011(4) 0.025(5) -0.005(3) 0.010(4) 0.001(4) C57B 0.011(4) 0.009(4) 0.024(5) 0.003(3) 0.009(4) 0.004(4) C65B 0.019(3) 0.015(3) 0.024(4) 0.006(2) -0.002(2) 0.006(3) C66B 0.021(3) 0.019(3) 0.021(4) 0.008(3) 0.003(3) 0.001(3) #============================================================================== _computing_data_collection 'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)' _computing_cell_refinement 'CrystalClear-SM Expert 2.0 r4' _computing_data_reduction 'CrystalClear-SM Expert 2.0 r4' _computing_structure_solution 'SIR2004 (Burla, et al., 2005)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2011)' _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 C32 1.340(3) yes . . F2 C51 1.322(3) yes . . F3 C60 1.307(4) yes . . F4 C32 1.330(3) yes . . F5 C61 1.313(3) yes . . F6 C60 1.318(4) yes . . F7 C51 1.301(3) yes . . F8 C60 1.324(4) yes . . F9 C61 1.320(4) yes . . F10 C61 1.305(4) yes . . F11 C51 1.335(3) yes . . F12 C32 1.325(3) yes . . O13 N25 1.229(3) yes . . O14 N26 1.227(3) yes . . O15 C46 1.215(3) yes . . O16 N26 1.229(3) yes . . O17 C45 1.204(3) yes . . O18 N25 1.230(4) yes . . O19 C29 1.359(3) yes . . O19 C50 1.443(3) yes . . O20 C41 1.361(3) yes . . O20 C56 1.443(3) yes . . O21 C37 1.216(3) yes . . O22 C33 1.356(3) yes . . O22 C38 1.453(3) yes . . O23 C33 1.202(3) yes . . O24 C45 1.349(3) yes . . O24 C58 1.453(3) yes . . N25 C52 1.475(4) yes . . N26 C39 1.475(3) yes . . C27 C43 1.401(3) yes . . C27 C44 1.395(3) yes . . C27 C46 1.464(3) yes . . C28 C45 1.492(3) yes . . C28 C47 1.390(3) yes . . C28 C64 1.397(3) yes . . C29 C36 1.394(3) yes . . C29 C48 1.400(4) yes . . C30 C33 1.495(3) yes . . C30 C53 1.387(4) yes . . C30 C55 1.388(3) yes . . C31 C40 1.379(3) yes . . C31 C41 1.398(3) yes . . C32 C59 1.534(5) yes . . C32 C57B 1.555(9) yes . . C34 C52 1.382(4) yes . . C34 C55 1.382(4) yes . . C35 C52 1.375(4) yes . . C35 C53 1.385(4) yes . . C36 C44 1.381(3) yes . . C37 C49 1.465(4) yes . . C37 C59 1.557(5) yes . . C37 C59B 1.599(8) yes . . C38 C57 1.516(5) yes . . C38 C57B 1.616(8) yes . . C39 C42 1.379(3) yes . . C39 C63 1.382(3) yes . . C40 C49 1.399(3) yes . . C41 C62 1.389(3) yes . . C42 C47 1.381(3) yes . . C43 C48 1.379(3) yes . . C46 C65 1.554(5) yes . . C46 C65B 1.580(7) yes . . C49 C54 1.394(3) yes . . C51 C57 1.537(5) yes . . C51 C59B 1.558(9) yes . . C54 C62 1.382(3) yes . . C57 C59 1.329(5) yes . . C58 C66 1.545(6) yes . . C58 C66B 1.523(7) yes . . C60 C66 1.579(6) yes . . C60 C65B 1.564(8) yes . . C61 C65 1.544(6) yes . . C61 C66B 1.605(8) yes . . C63 C64 1.384(3) yes . . C65 C66 1.317(8) yes . . C59B C57B 1.337(12) yes . . C65B C66B 1.340(8) yes . . 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 C29 O19 C50 117.71(19) yes . . . C41 O20 C56 117.93(19) yes . . . C33 O22 C38 116.70(18) yes . . . C45 O24 C58 116.98(18) yes . . . O13 N25 O18 124.1(3) yes . . . O13 N25 C52 118.1(3) yes . . . O18 N25 C52 117.7(2) yes . . . O14 N26 O16 123.8(2) yes . . . O14 N26 C39 118.2(2) yes . . . O16 N26 C39 118.0(2) yes . . . C43 C27 C44 118.8(2) yes . . . C43 C27 C46 121.7(2) yes . . . C44 C27 C46 119.5(2) yes . . . C45 C28 C47 121.3(2) yes . . . C45 C28 C64 118.1(2) yes . . . C47 C28 C64 120.6(2) yes . . . O19 C29 C36 124.2(2) yes . . . O19 C29 C48 115.6(2) yes . . . C36 C29 C48 120.3(2) yes . . . C33 C30 C53 121.9(2) yes . . . C33 C30 C55 117.9(2) yes . . . C53 C30 C55 120.2(2) yes . . . C40 C31 C41 120.0(2) yes . . . F1 C32 F4 107.65(19) yes . . . F1 C32 F12 106.54(19) yes . . . F1 C32 C59 114.2(2) yes . . . F1 C32 C57B 101.5(3) yes . . . F4 C32 F12 106.6(2) yes . . . F4 C32 C59 118.1(2) yes . . . F4 C32 C57B 95.2(3) yes . . . F12 C32 C59 102.7(2) yes . . . F12 C32 C57B 136.7(4) yes . . . O22 C33 O23 124.4(2) yes . . . O22 C33 C30 111.3(2) yes . . . O23 C33 C30 124.3(2) yes . . . C52 C34 C55 117.9(2) yes . . . C52 C35 C53 118.8(2) yes . . . C29 C36 C44 119.3(2) yes . . . O21 C37 C49 124.5(2) yes . . . O21 C37 C59 116.9(3) yes . . . O21 C37 C59B 112.7(3) yes . . . C49 C37 C59 117.4(2) yes . . . C49 C37 C59B 118.0(3) yes . . . O22 C38 C57 106.6(2) yes . . . O22 C38 C57B 104.1(3) yes . . . N26 C39 C42 118.3(2) yes . . . N26 C39 C63 118.5(2) yes . . . C42 C39 C63 123.3(2) yes . . . C31 C40 C49 119.9(2) yes . . . O20 C41 C31 115.0(2) yes . . . O20 C41 C62 124.5(2) yes . . . C31 C41 C62 120.5(2) yes . . . C39 C42 C47 118.3(2) yes . . . C27 C43 C48 120.7(2) yes . . . C27 C44 C36 121.2(2) yes . . . O17 C45 O24 123.9(2) yes . . . O17 C45 C28 124.4(2) yes . . . O24 C45 C28 111.7(2) yes . . . O15 C46 C27 124.9(2) yes . . . O15 C46 C65 113.7(3) yes . . . O15 C46 C65B 117.5(3) yes . . . C27 C46 C65 119.5(2) yes . . . C27 C46 C65B 114.2(3) yes . . . C28 C47 C42 119.9(2) yes . . . C29 C48 C43 119.7(2) yes . . . C37 C49 C40 121.4(2) yes . . . C37 C49 C54 119.2(2) yes . . . C40 C49 C54 119.4(2) yes . . . F2 C51 F7 107.4(2) yes . . . F2 C51 F11 107.0(2) yes . . . F2 C51 C57 106.3(2) yes . . . F2 C51 C59B 120.0(4) yes . . . F7 C51 F11 106.5(2) yes . . . F7 C51 C57 123.4(3) yes . . . F7 C51 C59B 86.1(3) yes . . . F11 C51 C57 105.4(2) yes . . . F11 C51 C59B 125.1(4) yes . . . N25 C52 C34 118.2(2) yes . . . N25 C52 C35 119.1(2) yes . . . C34 C52 C35 122.7(2) yes . . . C30 C53 C35 119.8(2) yes . . . C49 C54 C62 121.0(2) yes . . . C30 C55 C34 120.6(3) yes . . . C38 C57 C51 119.4(3) yes . . . C38 C57 C59 122.9(4) yes . . . C51 C57 C59 117.5(3) yes . . . O24 C58 C66 106.1(2) yes . . . O24 C58 C66B 107.5(3) yes . . . C32 C59 C37 119.4(3) yes . . . C32 C59 C57 117.2(3) yes . . . C37 C59 C57 123.3(4) yes . . . F3 C60 F6 108.7(2) yes . . . F3 C60 F8 106.2(2) yes . . . F3 C60 C66 101.2(3) yes . . . F3 C60 C65B 125.6(3) yes . . . F6 C60 F8 106.4(3) yes . . . F6 C60 C66 107.5(3) yes . . . F6 C60 C65B 114.9(3) yes . . . F8 C60 C66 126.0(3) yes . . . F8 C60 C65B 91.4(3) yes . . . F5 C61 F9 107.7(2) yes . . . F5 C61 F10 106.9(3) yes . . . F5 C61 C65 115.2(3) yes . . . F5 C61 C66B 101.9(3) yes . . . F9 C61 F10 105.6(3) yes . . . F9 C61 C65 122.5(3) yes . . . F9 C61 C66B 99.4(3) yes . . . F10 C61 C65 96.7(3) yes . . . F10 C61 C66B 133.3(3) yes . . . C41 C62 C54 119.1(2) yes . . . C39 C63 C64 118.1(2) yes . . . C28 C64 C63 119.8(2) yes . . . C46 C65 C61 124.0(4) yes . . . C46 C65 C66 121.3(4) yes . . . C61 C65 C66 114.6(4) yes . . . C58 C66 C60 121.4(4) yes . . . C58 C66 C65 122.1(4) yes . . . C60 C66 C65 116.5(4) yes . . . C37 C59B C51 133.1(6) yes . . . C37 C59B C57B 113.5(7) yes . . . C51 C59B C57B 113.2(6) yes . . . C32 C57B C38 128.6(6) yes . . . C32 C57B C59B 116.3(6) yes . . . C38 C57B C59B 115.1(7) yes . . . C46 C65B C60 128.5(4) yes . . . C46 C65B C66B 119.5(6) yes . . . C60 C65B C66B 111.8(6) yes . . . C58 C66B C61 125.7(4) yes . . . C58 C66B C65B 121.6(6) yes . . . C61 C66B C65B 112.5(6) yes . . . #============================================================================== #============================================================================== # 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 948162'