# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_urf _database_code_depnum_ccdc_archive 'CCDC 900136' #TrackingRef '13744_web_deposit_cif_file_0_RajeshG.Gonnade_1346846209.urf_uxf.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H11 F N2 O5' _chemical_formula_sum 'C9 H11 F N2 O5' _chemical_formula_weight 246.20 _chemical_absolute_configuration syn loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 15.4056(4) _cell_length_b 6.8529(2) _cell_length_c 15.8005(4) _cell_angle_alpha 90.00 _cell_angle_beta 116.0190(10) _cell_angle_gamma 90.00 _cell_volume 1499.04(7) _cell_formula_units_Z 6 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9928 _cell_measurement_theta_min 2.587 _cell_measurement_theta_max 32.407 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.59 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.636 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.146 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9191 _exptl_absorpt_correction_T_max 0.9856 _exptl_absorpt_process_details 'bruker sadabs' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD Area Detector' _diffrn_measurement_device 'BRUKER SMART APEX' _diffrn_measurement_method 'Omega and phi Scan' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 24993 _diffrn_reflns_av_R_equivalents 0.0251 _diffrn_reflns_av_sigmaI/netI 0.0295 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.54 _diffrn_reflns_theta_max 28.00 _reflns_number_total 7180 _reflns_number_gt 6731 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement 'SMART (Bruker, 2000)' _computing_data_reduction 'SAINT(Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0448P)^2^+0.4414P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.1(4) _refine_ls_number_reflns 7180 _refine_ls_number_parameters 484 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0376 _refine_ls_R_factor_gt 0.0342 _refine_ls_wR_factor_ref 0.0882 _refine_ls_wR_factor_gt 0.0861 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1A N 0.57976(11) 1.0491(2) 0.78990(10) 0.0162(3) Uani 1 1 d . . . C2A C 0.54524(12) 1.2003(3) 0.82569(12) 0.0167(3) Uani 1 1 d . . . N3A N 0.52956(11) 1.1476(2) 0.90205(10) 0.0181(3) Uani 1 1 d . . . H3A H 0.5076 1.2398 0.9263 0.022 Uiso 1 1 calc R . . C4A C 0.54427(12) 0.9667(3) 0.94489(12) 0.0171(4) Uani 1 1 d . . . C5A C 0.58001(13) 0.8188(3) 0.90365(13) 0.0182(4) Uani 1 1 d . . . H5A H 0.5917 0.6902 0.9287 0.022 Uiso 1 1 calc R . . C6A C 0.59666(12) 0.8644(3) 0.82944(12) 0.0176(3) Uani 1 1 d . . . H6A H 0.6210 0.7663 0.8031 0.021 Uiso 1 1 calc R . . C1'A C 0.59203(12) 1.0869(3) 0.70476(12) 0.0149(3) Uani 1 1 d . . . H1'A H 0.5622 1.2155 0.6775 0.018 Uiso 1 1 calc R . . C2'A C 0.69631(12) 1.0831(3) 0.71819(13) 0.0160(3) Uani 1 1 d . . . H2'A H 0.7330 0.9780 0.7638 0.019 Uiso 1 1 calc R . . O2'A O 0.74050(10) 1.26479(19) 0.75131(10) 0.0230(3) Uani 1 1 d . . . H2AA H 0.797(3) 1.247(6) 0.765(3) 0.076(12) Uiso 1 1 d . . . C3'A C 0.68197(13) 1.0284(3) 0.61976(13) 0.0189(4) Uani 1 1 d . . . H3'A H 0.7417 0.9721 0.6194 0.023 Uiso 1 1 calc R . . F3'A F 0.64936(9) 1.19573(18) 0.56269(8) 0.0283(3) Uani 1 1 d . . . C4'A C 0.60003(13) 0.8822(3) 0.58854(13) 0.0181(4) Uani 1 1 d . . . H4'A H 0.5586 0.8988 0.5195 0.022 Uiso 1 1 calc R . . O4'A O 0.54430(8) 0.9363(2) 0.63888(8) 0.0177(3) Uani 1 1 d . . . C5'A C 0.63162(15) 0.6720(3) 0.60750(14) 0.0246(4) Uani 1 1 d . . . H5"A H 0.5750 0.5877 0.5947 0.030 Uiso 1 1 calc R . . H5'A H 0.6605 0.6311 0.5654 0.030 Uiso 1 1 calc R . . O5'A O 0.70036(11) 0.6509(2) 0.70275(10) 0.0251(3) Uani 1 1 d . . . H5AA H 0.7070(17) 0.540(4) 0.7131(17) 0.025(6) Uiso 1 1 d . . . N1B N 0.95842(10) 0.6710(2) 0.81068(10) 0.0144(3) Uani 1 1 d . . . C2B C 0.92919(12) 0.5110(3) 0.84435(12) 0.0163(3) Uani 1 1 d . . . O2B O 0.93305(10) 0.34437(18) 0.81776(9) 0.0211(3) Uani 1 1 d . . . N3B N 0.89428(11) 0.5509(2) 0.90840(10) 0.0172(3) Uani 1 1 d . . . H3B H 0.8769 0.4501 0.9319 0.021 Uiso 1 1 calc R . . C4B C 0.88345(13) 0.7335(3) 0.94016(13) 0.0187(4) Uani 1 1 d . . . O4B O 0.84953(11) 0.7432(2) 0.99734(10) 0.0270(3) Uani 1 1 d . . . C5B C 0.91481(13) 0.8936(3) 0.90178(12) 0.0165(3) Uani 1 1 d . . . H5B H 0.9105 1.0236 0.9205 0.020 Uiso 1 1 calc R . . C6B C 0.95020(12) 0.8585(3) 0.83939(12) 0.0158(3) Uani 1 1 d . . . H6B H 0.9703 0.9656 0.8141 0.019 Uiso 1 1 calc R . . C1'B C 0.99024(12) 0.6387(2) 0.73643(12) 0.0139(3) Uani 1 1 d . . . H1'B H 1.0197 0.5060 0.7442 0.017 Uiso 1 1 calc R . . C2'B C 0.90863(12) 0.6588(2) 0.63642(12) 0.0140(3) Uani 1 1 d . . . H2'B H 0.8596 0.7542 0.6367 0.017 Uiso 1 1 calc R . . O2'B O 0.86416(10) 0.47767(19) 0.60339(9) 0.0197(3) Uani 1 1 d . . . H2BB H 0.8317(19) 0.487(5) 0.543(2) 0.045(8) Uiso 1 1 d . . . C3'B C 0.96194(12) 0.7463(3) 0.58339(12) 0.0166(3) Uani 1 1 d . . . H3'B H 0.9178 0.8214 0.5264 0.020 Uiso 1 1 calc R . . F3'B F 1.00890(8) 0.59244(18) 0.56069(8) 0.0242(2) Uani 1 1 d . . . C4'B C 1.03770(13) 0.8753(3) 0.65647(12) 0.0170(3) Uani 1 1 d . . . H4'B H 1.0969 0.8739 0.6455 0.020 Uiso 1 1 calc R . . O4'B O 1.06010(8) 0.78082(19) 0.74601(9) 0.0166(3) Uani 1 1 d . . . C5'B C 1.00721(13) 1.0854(3) 0.65699(13) 0.0194(4) Uani 1 1 d . . . H5"B H 1.0506 1.1484 0.7172 0.023 Uiso 1 1 calc R . . H5'B H 1.0119 1.1582 0.6050 0.023 Uiso 1 1 calc R . . O5'B O 0.91027(9) 1.0904(2) 0.64582(10) 0.0197(3) Uani 1 1 d . . . H5BB H 0.8964(18) 1.203(4) 0.6442(18) 0.034(7) Uiso 1 1 d . . . N1C N 0.71872(10) 0.1460(2) 0.16498(10) 0.0155(3) Uani 1 1 d . . . C2C C 0.75605(13) -0.0036(3) 0.13318(12) 0.0170(3) Uani 1 1 d . . . O2C O 0.76066(11) -0.17335(19) 0.16140(10) 0.0236(3) Uani 1 1 d . . . N3C N 0.78874(11) 0.0452(2) 0.06905(11) 0.0166(3) Uani 1 1 d . . . H2C H 0.8107 -0.0506 0.0468 0.020 Uiso 1 1 calc R . . C4C C 0.79099(13) 0.2306(3) 0.03509(12) 0.0181(3) Uani 1 1 d . . . O4C O 0.82730(11) 0.2503(2) -0.02010(10) 0.0265(3) Uani 1 1 d . . . C5C C 0.74988(13) 0.3807(3) 0.06970(12) 0.0182(3) Uani 1 1 d . . . H5C H 0.7468 0.5116 0.0487 0.022 Uiso 1 1 calc R . . C6C C 0.71571(12) 0.3341(3) 0.13219(12) 0.0163(3) Uani 1 1 d . . . H6C H 0.6885 0.4342 0.1546 0.020 Uiso 1 1 calc R . . O2A O 0.52915(10) 1.3639(2) 0.79278(10) 0.0244(3) Uani 1 1 d . . . O4A O 0.52718(10) 0.9475(2) 1.01359(9) 0.0235(3) Uani 1 1 d . . . C1'C C 0.67834(12) 0.0918(3) 0.23112(12) 0.0151(3) Uani 1 1 d . . . H1'C H 0.6254 -0.0063 0.2018 0.018 Uiso 1 1 calc R . . C2'C C 0.75406(13) 0.0195(3) 0.32723(13) 0.0184(4) Uani 1 1 d . . . H2'C H 0.8150 0.0952 0.3446 0.022 Uiso 1 1 calc R . . O2'C O 0.77605(12) -0.1816(2) 0.33290(12) 0.0298(4) Uani 1 1 d . . . H2CC H 0.768(3) -0.204(8) 0.280(3) 0.122(18) Uiso 1 1 d . . . C3'C C 0.71084(13) 0.0769(3) 0.39371(13) 0.0177(4) Uani 1 1 d . . . H3'C H 0.7622 0.1242 0.4552 0.021 Uiso 1 1 calc R . . F3'C F 0.66057(9) -0.08122(16) 0.40733(8) 0.0249(3) Uani 1 1 d . . . C4'C C 0.63994(12) 0.2415(3) 0.34174(12) 0.0162(3) Uani 1 1 d . . . H4'C H 0.5734 0.2016 0.3306 0.019 Uiso 1 1 calc R . . O4'C O 0.64280(9) 0.26435(19) 0.25226(8) 0.0180(3) Uani 1 1 d . . . C5'C C 0.66315(12) 0.4370(3) 0.39034(12) 0.0164(3) Uani 1 1 d . . . H5"C H 0.6206 0.5381 0.3474 0.020 Uiso 1 1 calc R . . H5'C H 0.6512 0.4324 0.4470 0.020 Uiso 1 1 calc R . . O5'C O 0.76213(9) 0.4867(2) 0.41716(9) 0.0193(3) Uani 1 1 d . . . H5CC H 0.7641(18) 0.597(4) 0.3890(17) 0.035(7) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1A 0.0207(7) 0.0150(7) 0.0151(7) 0.0009(6) 0.0098(6) 0.0025(6) C2A 0.0187(8) 0.0164(9) 0.0154(8) -0.0007(7) 0.0077(7) 0.0009(7) N3A 0.0237(8) 0.0163(8) 0.0176(7) -0.0005(6) 0.0122(6) 0.0024(6) C4A 0.0177(8) 0.0178(9) 0.0137(8) -0.0006(7) 0.0050(7) -0.0036(7) C5A 0.0227(9) 0.0141(9) 0.0173(8) 0.0022(7) 0.0084(7) -0.0002(7) C6A 0.0179(8) 0.0142(8) 0.0192(8) -0.0005(7) 0.0067(7) 0.0004(7) C1'A 0.0192(8) 0.0115(8) 0.0154(8) 0.0008(7) 0.0090(7) 0.0012(6) C2'A 0.0173(8) 0.0103(8) 0.0200(8) 0.0032(7) 0.0080(7) 0.0002(6) O2'A 0.0220(7) 0.0121(6) 0.0328(8) 0.0001(6) 0.0101(6) -0.0025(5) C3'A 0.0226(9) 0.0151(9) 0.0240(9) 0.0067(7) 0.0147(8) 0.0060(7) F3'A 0.0422(7) 0.0216(6) 0.0289(6) 0.0120(5) 0.0230(5) 0.0072(5) C4'A 0.0222(8) 0.0184(9) 0.0161(8) -0.0003(7) 0.0108(7) 0.0029(7) O4'A 0.0182(6) 0.0205(7) 0.0161(6) -0.0043(5) 0.0090(5) -0.0026(5) C5'A 0.0295(10) 0.0199(10) 0.0223(9) -0.0045(8) 0.0095(8) 0.0024(8) O5'A 0.0316(8) 0.0111(7) 0.0262(7) 0.0005(6) 0.0067(6) 0.0028(5) N1B 0.0183(7) 0.0117(7) 0.0144(7) -0.0007(6) 0.0081(6) 0.0002(5) C2B 0.0181(8) 0.0156(9) 0.0150(8) 0.0002(7) 0.0072(7) -0.0004(7) O2B 0.0310(7) 0.0110(6) 0.0272(7) -0.0014(5) 0.0182(6) -0.0010(5) N3B 0.0252(8) 0.0117(7) 0.0184(7) 0.0017(6) 0.0129(6) 0.0001(6) C4B 0.0225(8) 0.0158(9) 0.0183(8) -0.0023(7) 0.0095(7) 0.0012(7) O4B 0.0464(8) 0.0172(7) 0.0311(7) 0.0006(6) 0.0296(7) 0.0021(6) C5B 0.0217(8) 0.0109(8) 0.0169(8) -0.0003(7) 0.0083(7) 0.0014(6) C6B 0.0187(8) 0.0109(8) 0.0168(8) -0.0011(7) 0.0069(7) -0.0010(6) C1'B 0.0162(8) 0.0108(8) 0.0161(8) 0.0000(6) 0.0084(6) -0.0003(6) C2'B 0.0166(8) 0.0104(8) 0.0141(8) 0.0003(6) 0.0060(6) 0.0003(6) O2'B 0.0255(7) 0.0114(6) 0.0169(6) -0.0011(5) 0.0045(5) -0.0044(5) C3'B 0.0221(8) 0.0127(8) 0.0180(8) -0.0004(7) 0.0115(7) 0.0022(7) F3'B 0.0309(6) 0.0217(6) 0.0268(6) -0.0063(5) 0.0189(5) 0.0023(5) C4'B 0.0207(8) 0.0156(9) 0.0189(8) -0.0003(7) 0.0126(7) -0.0011(7) O4'B 0.0161(6) 0.0156(6) 0.0180(6) 0.0000(5) 0.0075(5) -0.0035(5) C5'B 0.0241(9) 0.0120(8) 0.0250(9) -0.0005(7) 0.0134(7) -0.0030(7) O5'B 0.0234(7) 0.0112(6) 0.0260(7) -0.0001(5) 0.0121(5) 0.0018(5) N1C 0.0181(7) 0.0124(7) 0.0187(7) -0.0013(6) 0.0107(6) -0.0012(5) C2C 0.0196(8) 0.0148(8) 0.0186(8) -0.0017(7) 0.0102(7) -0.0013(7) O2C 0.0408(8) 0.0109(6) 0.0301(7) 0.0010(5) 0.0258(7) 0.0014(5) N3C 0.0241(7) 0.0107(7) 0.0190(7) -0.0015(6) 0.0132(6) 0.0003(6) C4C 0.0216(8) 0.0149(8) 0.0181(8) -0.0002(7) 0.0088(7) -0.0020(7) O4C 0.0443(8) 0.0178(7) 0.0293(7) 0.0006(6) 0.0272(7) -0.0020(6) C5C 0.0216(8) 0.0124(8) 0.0188(8) 0.0033(7) 0.0072(7) 0.0013(7) C6C 0.0171(8) 0.0133(9) 0.0170(8) -0.0012(7) 0.0061(7) 0.0013(6) O2A 0.0385(8) 0.0166(7) 0.0253(7) 0.0045(6) 0.0206(6) 0.0076(6) O4A 0.0336(8) 0.0226(7) 0.0196(6) 0.0002(5) 0.0165(6) -0.0036(6) C1'C 0.0173(8) 0.0136(8) 0.0184(8) -0.0026(7) 0.0116(7) -0.0008(6) C2'C 0.0228(9) 0.0130(9) 0.0230(9) 0.0032(7) 0.0134(7) 0.0015(7) O2'C 0.0554(10) 0.0145(7) 0.0360(8) 0.0107(6) 0.0350(8) 0.0129(6) C3'C 0.0239(9) 0.0119(8) 0.0184(8) 0.0016(7) 0.0103(7) -0.0017(7) F3'C 0.0407(6) 0.0154(5) 0.0303(6) 0.0027(5) 0.0263(5) -0.0015(5) C4'C 0.0193(8) 0.0157(8) 0.0156(8) -0.0020(7) 0.0095(7) -0.0005(7) O4'C 0.0238(6) 0.0179(7) 0.0138(6) 0.0009(5) 0.0096(5) 0.0058(5) C5'C 0.0206(8) 0.0135(8) 0.0168(8) 0.0002(7) 0.0099(7) -0.0001(7) O5'C 0.0209(6) 0.0152(6) 0.0184(6) 0.0026(5) 0.0056(5) -0.0034(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1A C6A 1.384(2) . ? N1A C2A 1.393(2) . ? N1A C1'A 1.461(2) . ? C2A O2A 1.215(2) . ? C2A N3A 1.378(2) . ? N3A C4A 1.383(2) . ? N3A H3A 0.8800 . ? C4A O4A 1.231(2) . ? C4A C5A 1.439(3) . ? C5A C6A 1.342(3) . ? C5A H5A 0.9500 . ? C6A H6A 0.9500 . ? C1'A O4'A 1.421(2) . ? C1'A C2'A 1.526(2) . ? C1'A H1'A 1.0000 . ? C2'A O2'A 1.406(2) . ? C2'A C3'A 1.519(3) . ? C2'A H2'A 1.0000 . ? O2'A H2AA 0.81(4) . ? C3'A F3'A 1.408(2) . ? C3'A C4'A 1.514(3) . ? C3'A H3'A 1.0000 . ? C4'A O4'A 1.451(2) . ? C4'A C5'A 1.508(3) . ? C4'A H4'A 1.0000 . ? C5'A O5'A 1.417(2) . ? C5'A H5"A 0.9900 . ? C5'A H5'A 0.9900 . ? O5'A H5AA 0.77(3) . ? N1B C2B 1.378(2) . ? N1B C6B 1.387(2) . ? N1B C1'B 1.473(2) . ? C2B O2B 1.227(2) . ? C2B N3B 1.366(2) . ? N3B C4B 1.385(2) . ? N3B H3B 0.8800 . ? C4B O4B 1.228(2) . ? C4B C5B 1.436(3) . ? C5B C6B 1.341(2) . ? C5B H5B 0.9500 . ? C6B H6B 0.9500 . ? C1'B O4'B 1.409(2) . ? C1'B C2'B 1.534(2) . ? C1'B H1'B 1.0000 . ? C2'B O2'B 1.403(2) . ? C2'B C3'B 1.530(2) . ? C2'B H2'B 1.0000 . ? O2'B H2BB 0.87(3) . ? C3'B F3'B 1.411(2) . ? C3'B C4'B 1.515(3) . ? C3'B H3'B 1.0000 . ? C4'B O4'B 1.453(2) . ? C4'B C5'B 1.516(3) . ? C4'B H4'B 1.0000 . ? C5'B O5'B 1.425(2) . ? C5'B H5"B 0.9900 . ? C5'B H5'B 0.9900 . ? O5'B H5BB 0.80(3) . ? N1C C2C 1.374(2) . ? N1C C6C 1.382(2) . ? N1C C1'C 1.479(2) . ? C2C O2C 1.237(2) . ? C2C N3C 1.357(2) . ? N3C C4C 1.386(2) . ? N3C H2C 0.8800 . ? C4C O4C 1.233(2) . ? C4C C5C 1.436(3) . ? C5C C6C 1.345(3) . ? C5C H5C 0.9500 . ? C6C H6C 0.9500 . ? C1'C O4'C 1.404(2) . ? C1'C C2'C 1.536(2) . ? C1'C H1'C 1.0000 . ? C2'C O2'C 1.412(2) . ? C2'C C3'C 1.522(3) . ? C2'C H2'C 1.0000 . ? O2'C H2CC 0.81(5) . ? C3'C F3'C 1.402(2) . ? C3'C C4'C 1.534(2) . ? C3'C H3'C 1.0000 . ? C4'C O4'C 1.442(2) . ? C4'C C5'C 1.507(2) . ? C4'C H4'C 1.0000 . ? C5'C O5'C 1.433(2) . ? C5'C H5"C 0.9900 . ? C5'C H5'C 0.9900 . ? O5'C H5CC 0.88(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6A N1A C2A 121.76(15) . . ? C6A N1A C1'A 120.21(15) . . ? C2A N1A C1'A 117.92(14) . . ? O2A C2A N3A 122.36(17) . . ? O2A C2A N1A 123.73(16) . . ? N3A C2A N1A 113.90(16) . . ? C2A N3A C4A 127.54(16) . . ? C2A N3A H3A 116.2 . . ? C4A N3A H3A 116.2 . . ? O4A C4A N3A 118.37(17) . . ? O4A C4A C5A 126.60(17) . . ? N3A C4A C5A 115.03(15) . . ? C6A C5A C4A 119.28(17) . . ? C6A C5A H5A 120.4 . . ? C4A C5A H5A 120.4 . . ? C5A C6A N1A 122.49(17) . . ? C5A C6A H6A 118.8 . . ? N1A C6A H6A 118.8 . . ? O4'A C1'A N1A 108.12(14) . . ? O4'A C1'A C2'A 105.32(13) . . ? N1A C1'A C2'A 114.99(14) . . ? O4'A C1'A H1'A 109.4 . . ? N1A C1'A H1'A 109.4 . . ? C2'A C1'A H1'A 109.4 . . ? O2'A C2'A C3'A 115.40(15) . . ? O2'A C2'A C1'A 110.18(14) . . ? C3'A C2'A C1'A 100.99(14) . . ? O2'A C2'A H2'A 110.0 . . ? C3'A C2'A H2'A 110.0 . . ? C1'A C2'A H2'A 110.0 . . ? C2'A O2'A H2AA 105(3) . . ? F3'A C3'A C4'A 108.53(15) . . ? F3'A C3'A C2'A 107.79(14) . . ? C4'A C3'A C2'A 102.87(14) . . ? F3'A C3'A H3'A 112.4 . . ? C4'A C3'A H3'A 112.4 . . ? C2'A C3'A H3'A 112.4 . . ? O4'A C4'A C5'A 110.61(16) . . ? O4'A C4'A C3'A 105.16(14) . . ? C5'A C4'A C3'A 114.64(15) . . ? O4'A C4'A H4'A 108.8 . . ? C5'A C4'A H4'A 108.8 . . ? C3'A C4'A H4'A 108.8 . . ? C1'A O4'A C4'A 110.28(13) . . ? O5'A C5'A C4'A 109.53(15) . . ? O5'A C5'A H5"A 109.8 . . ? C4'A C5'A H5"A 109.8 . . ? O5'A C5'A H5'A 109.8 . . ? C4'A C5'A H5'A 109.8 . . ? H5"A C5'A H5'A 108.2 . . ? C5'A O5'A H5AA 107.0(18) . . ? C2B N1B C6B 121.26(15) . . ? C2B N1B C1'B 117.84(14) . . ? C6B N1B C1'B 120.65(14) . . ? O2B C2B N3B 122.27(16) . . ? O2B C2B N1B 122.36(16) . . ? N3B C2B N1B 115.36(16) . . ? C2B N3B C4B 126.75(15) . . ? C2B N3B H3B 116.6 . . ? C4B N3B H3B 116.6 . . ? O4B C4B N3B 118.25(17) . . ? O4B C4B C5B 126.85(18) . . ? N3B C4B C5B 114.89(15) . . ? C6B C5B C4B 119.63(16) . . ? C6B C5B H5B 120.2 . . ? C4B C5B H5B 120.2 . . ? C5B C6B N1B 122.09(16) . . ? C5B C6B H6B 119.0 . . ? N1B C6B H6B 119.0 . . ? O4'B C1'B N1B 108.41(13) . . ? O4'B C1'B C2'B 106.91(13) . . ? N1B C1'B C2'B 113.47(14) . . ? O4'B C1'B H1'B 109.3 . . ? N1B C1'B H1'B 109.3 . . ? C2'B C1'B H1'B 109.3 . . ? O2'B C2'B C3'B 115.78(14) . . ? O2'B C2'B C1'B 110.45(14) . . ? C3'B C2'B C1'B 101.83(13) . . ? O2'B C2'B H2'B 109.5 . . ? C3'B C2'B H2'B 109.5 . . ? C1'B C2'B H2'B 109.5 . . ? C2'B O2'B H2BB 107(2) . . ? F3'B C3'B C4'B 108.68(14) . . ? F3'B C3'B C2'B 107.74(14) . . ? C4'B C3'B C2'B 103.33(14) . . ? F3'B C3'B H3'B 112.2 . . ? C4'B C3'B H3'B 112.2 . . ? C2'B C3'B H3'B 112.2 . . ? O4'B C4'B C3'B 104.86(14) . . ? O4'B C4'B C5'B 111.09(14) . . ? C3'B C4'B C5'B 114.93(15) . . ? O4'B C4'B H4'B 108.6 . . ? C3'B C4'B H4'B 108.6 . . ? C5'B C4'B H4'B 108.6 . . ? C1'B O4'B C4'B 111.05(12) . . ? O5'B C5'B C4'B 109.41(14) . . ? O5'B C5'B H5"B 109.8 . . ? C4'B C5'B H5"B 109.8 . . ? O5'B C5'B H5'B 109.8 . . ? C4'B C5'B H5'B 109.8 . . ? H5"B C5'B H5'B 108.2 . . ? C5'B O5'B H5BB 106.1(19) . . ? C2C N1C C6C 120.62(15) . . ? C2C N1C C1'C 116.35(14) . . ? C6C N1C C1'C 122.95(14) . . ? O2C C2C N3C 121.32(17) . . ? O2C C2C N1C 122.50(16) . . ? N3C C2C N1C 116.18(16) . . ? C2C N3C C4C 126.58(15) . . ? C2C N3C H2C 116.7 . . ? C4C N3C H2C 116.7 . . ? O4C C4C N3C 118.07(17) . . ? O4C C4C C5C 127.14(18) . . ? N3C C4C C5C 114.78(16) . . ? C6C C5C C4C 119.28(17) . . ? C6C C5C H5C 120.4 . . ? C4C C5C H5C 120.4 . . ? C5C C6C N1C 122.49(16) . . ? C5C C6C H6C 118.8 . . ? N1C C6C H6C 118.8 . . ? O4'C C1'C N1C 106.56(14) . . ? O4'C C1'C C2'C 104.06(14) . . ? N1C C1'C C2'C 114.03(14) . . ? O4'C C1'C H1'C 110.6 . . ? N1C C1'C H1'C 110.6 . . ? C2'C C1'C H1'C 110.6 . . ? O2'C C2'C C3'C 111.97(15) . . ? O2'C C2'C C1'C 115.75(16) . . ? C3'C C2'C C1'C 103.09(14) . . ? O2'C C2'C H2'C 108.6 . . ? C3'C C2'C H2'C 108.6 . . ? C1'C C2'C H2'C 108.6 . . ? C2'C O2'C H2CC 101(4) . . ? F3'C C3'C C2'C 110.13(15) . . ? F3'C C3'C C4'C 109.81(14) . . ? C2'C C3'C C4'C 104.19(14) . . ? F3'C C3'C H3'C 110.8 . . ? C2'C C3'C H3'C 110.8 . . ? C4'C C3'C H3'C 110.8 . . ? O4'C C4'C C5'C 107.48(14) . . ? O4'C C4'C C3'C 106.50(13) . . ? C5'C C4'C C3'C 115.26(14) . . ? O4'C C4'C H4'C 109.1 . . ? C5'C C4'C H4'C 109.1 . . ? C3'C C4'C H4'C 109.1 . . ? C1'C O4'C C4'C 108.93(13) . . ? O5'C C5'C C4'C 110.23(14) . . ? O5'C C5'C H5"C 109.6 . . ? C4'C C5'C H5"C 109.6 . . ? O5'C C5'C H5'C 109.6 . . ? C4'C C5'C H5'C 109.6 . . ? H5"C C5'C H5'C 108.1 . . ? C5'C O5'C H5CC 108.8(16) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6A N1A C2A O2A -179.69(17) . . . . ? C1'A N1A C2A O2A -3.6(3) . . . . ? C6A N1A C2A N3A -0.4(2) . . . . ? C1'A N1A C2A N3A 175.70(14) . . . . ? O2A C2A N3A C4A 179.39(18) . . . . ? N1A C2A N3A C4A 0.1(3) . . . . ? C2A N3A C4A O4A 179.15(16) . . . . ? C2A N3A C4A C5A -0.1(3) . . . . ? O4A C4A C5A C6A -178.78(17) . . . . ? N3A C4A C5A C6A 0.4(2) . . . . ? C4A C5A C6A N1A -0.7(3) . . . . ? C2A N1A C6A C5A 0.7(3) . . . . ? C1'A N1A C6A C5A -175.27(16) . . . . ? C6A N1A C1'A O4'A 47.4(2) . . . . ? C2A N1A C1'A O4'A -128.73(16) . . . . ? C6A N1A C1'A C2'A -69.9(2) . . . . ? C2A N1A C1'A C2'A 113.94(17) . . . . ? O4'A C1'A C2'A O2'A 157.43(14) . . . . ? N1A C1'A C2'A O2'A -83.66(19) . . . . ? O4'A C1'A C2'A C3'A 34.95(17) . . . . ? N1A C1'A C2'A C3'A 153.86(14) . . . . ? O2'A C2'A C3'A F3'A -42.3(2) . . . . ? C1'A C2'A C3'A F3'A 76.42(16) . . . . ? O2'A C2'A C3'A C4'A -156.91(14) . . . . ? C1'A C2'A C3'A C4'A -38.14(16) . . . . ? F3'A C3'A C4'A O4'A -85.57(16) . . . . ? C2'A C3'A C4'A O4'A 28.46(17) . . . . ? F3'A C3'A C4'A C5'A 152.73(15) . . . . ? C2'A C3'A C4'A C5'A -93.24(18) . . . . ? N1A C1'A O4'A C4'A -141.52(14) . . . . ? C2'A C1'A O4'A C4'A -18.12(18) . . . . ? C5'A C4'A O4'A C1'A 117.72(16) . . . . ? C3'A C4'A O4'A C1'A -6.57(18) . . . . ? O4'A C4'A C5'A O5'A -68.2(2) . . . . ? C3'A C4'A C5'A O5'A 50.5(2) . . . . ? C6B N1B C2B O2B 177.72(17) . . . . ? C1'B N1B C2B O2B 3.4(2) . . . . ? C6B N1B C2B N3B -1.4(2) . . . . ? C1'B N1B C2B N3B -175.73(14) . . . . ? O2B C2B N3B C4B -177.34(17) . . . . ? N1B C2B N3B C4B 1.8(3) . . . . ? C2B N3B C4B O4B 179.05(17) . . . . ? C2B N3B C4B C5B -1.4(3) . . . . ? O4B C4B C5B C6B -179.82(18) . . . . ? N3B C4B C5B C6B 0.7(2) . . . . ? C4B C5B C6B N1B -0.5(3) . . . . ? C2B N1B C6B C5B 0.8(3) . . . . ? C1'B N1B C6B C5B 175.05(16) . . . . ? C2B N1B C1'B O4'B -149.70(14) . . . . ? C6B N1B C1'B O4'B 35.9(2) . . . . ? C2B N1B C1'B C2'B 91.70(18) . . . . ? C6B N1B C1'B C2'B -82.69(19) . . . . ? O4'B C1'B C2'B O2'B 149.79(14) . . . . ? N1B C1'B C2'B O2'B -90.75(17) . . . . ? O4'B C1'B C2'B C3'B 26.27(16) . . . . ? N1B C1'B C2'B C3'B 145.72(14) . . . . ? O2'B C2'B C3'B F3'B -38.95(19) . . . . ? C1'B C2'B C3'B F3'B 80.89(15) . . . . ? O2'B C2'B C3'B C4'B -153.87(14) . . . . ? C1'B C2'B C3'B C4'B -34.03(16) . . . . ? F3'B C3'B C4'B O4'B -83.93(15) . . . . ? C2'B C3'B C4'B O4'B 30.32(17) . . . . ? F3'B C3'B C4'B C5'B 153.81(14) . . . . ? C2'B C3'B C4'B C5'B -91.95(17) . . . . ? N1B C1'B O4'B C4'B -130.51(14) . . . . ? C2'B C1'B O4'B C4'B -7.84(17) . . . . ? C3'B C4'B O4'B C1'B -14.32(17) . . . . ? C5'B C4'B O4'B C1'B 110.41(16) . . . . ? O4'B C4'B C5'B O5'B -76.86(18) . . . . ? C3'B C4'B C5'B O5'B 42.0(2) . . . . ? C6C N1C C2C O2C 179.42(17) . . . . ? C1'C N1C C2C O2C -3.6(3) . . . . ? C6C N1C C2C N3C 0.0(2) . . . . ? C1'C N1C C2C N3C 176.91(14) . . . . ? O2C C2C N3C C4C -177.24(18) . . . . ? N1C C2C N3C C4C 2.2(3) . . . . ? C2C N3C C4C O4C 176.75(17) . . . . ? C2C N3C C4C C5C -3.1(3) . . . . ? O4C C4C C5C C6C -178.05(18) . . . . ? N3C C4C C5C C6C 1.7(2) . . . . ? C4C C5C C6C N1C 0.2(3) . . . . ? C2C N1C C6C C5C -1.1(3) . . . . ? C1'C N1C C6C C5C -177.82(16) . . . . ? C2C N1C C1'C O4'C -178.67(14) . . . . ? C6C N1C C1'C O4'C -1.8(2) . . . . ? C2C N1C C1'C C2'C 67.1(2) . . . . ? C6C N1C C1'C C2'C -116.01(18) . . . . ? O4'C C1'C C2'C O2'C 157.83(15) . . . . ? N1C C1'C C2'C O2'C -86.49(19) . . . . ? O4'C C1'C C2'C C3'C 35.24(17) . . . . ? N1C C1'C C2'C C3'C 150.92(14) . . . . ? O2'C C2'C C3'C F3'C -29.3(2) . . . . ? C1'C C2'C C3'C F3'C 95.77(16) . . . . ? O2'C C2'C C3'C C4'C -147.02(16) . . . . ? C1'C C2'C C3'C C4'C -21.94(18) . . . . ? F3'C C3'C C4'C O4'C -115.93(15) . . . . ? C2'C C3'C C4'C O4'C 2.00(18) . . . . ? F3'C C3'C C4'C C5'C 124.98(15) . . . . ? C2'C C3'C C4'C C5'C -117.09(16) . . . . ? N1C C1'C O4'C C4'C -156.37(13) . . . . ? C2'C C1'C O4'C C4'C -35.54(16) . . . . ? C5'C C4'C O4'C C1'C 145.40(14) . . . . ? C3'C C4'C O4'C C1'C 21.35(17) . . . . ? O4'C C4'C C5'C O5'C -68.65(17) . . . . ? C3'C C4'C C5'C O5'C 49.9(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.298 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.052 data_uxf _database_code_depnum_ccdc_archive 'CCDC 900137' #TrackingRef '13744_web_deposit_cif_file_0_RajeshG.Gonnade_1346846209.urf_uxf.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H11 F N2 O5' _chemical_formula_sum 'C9 H11 F N2 O5' _chemical_formula_weight 246.20 _chemical_absolute_configuration syn loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.3007(3) _cell_length_b 7.3372(3) _cell_length_c 10.8989(4) _cell_angle_alpha 90.00 _cell_angle_beta 92.277(2) _cell_angle_gamma 90.00 _cell_volume 503.45(4) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3861 _cell_measurement_theta_min 3.347 _cell_measurement_theta_max 35.965 _exptl_crystal_description PLATE _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.624 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 256 _exptl_absorpt_coefficient_mu 0.144 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9209 _exptl_absorpt_correction_T_max 0.9689 _exptl_absorpt_process_details 'bruker sadabs' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD Area Detector' _diffrn_measurement_device 'BRUKER SMART APEX' _diffrn_measurement_method 'Omega and phi Scan' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 10593 _diffrn_reflns_av_R_equivalents 0.0175 _diffrn_reflns_av_sigmaI/netI 0.0150 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 27.99 _reflns_number_total 2440 _reflns_number_gt 2398 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement 'SMART (Bruker, 2000)' _computing_data_reduction 'SAINT(Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0411P)^2^+0.0860P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.2(5) _refine_ls_number_reflns 2440 _refine_ls_number_parameters 162 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0242 _refine_ls_R_factor_gt 0.0239 _refine_ls_wR_factor_ref 0.0645 _refine_ls_wR_factor_gt 0.0643 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.47406(14) 0.36657(12) 0.67635(8) 0.01239(18) Uani 1 1 d . . . C2 C 0.57898(17) 0.20895(15) 0.64289(9) 0.0129(2) Uani 1 1 d . . . O2 O 0.51861(13) 0.05696(11) 0.67062(7) 0.01706(17) Uani 1 1 d . . . N3 N 0.75618(15) 0.23867(13) 0.57358(9) 0.01341(18) Uani 1 1 d . . . H3 H 0.8262 0.1416 0.5504 0.016 Uiso 1 1 calc R . . C4 C 0.83316(16) 0.40584(15) 0.53749(9) 0.01236(19) Uani 1 1 d . . . O4 O 0.98589(13) 0.41322(11) 0.46850(7) 0.01487(17) Uani 1 1 d . . . C5 C 0.72593(17) 0.56182(14) 0.58506(10) 0.0136(2) Uani 1 1 d . . . H5 H 0.7778 0.6812 0.5708 0.016 Uiso 1 1 calc R . . C6 C 0.55141(17) 0.53685(15) 0.65001(9) 0.0131(2) Uani 1 1 d . . . H6 H 0.4786 0.6408 0.6788 0.016 Uiso 1 1 calc R . . C1' C 0.26234(16) 0.34233(14) 0.73120(9) 0.0119(2) Uani 1 1 d . . . H1' H 0.1774 0.2512 0.6819 0.014 Uiso 1 1 calc R . . C2' C 0.27514(18) 0.28288(16) 0.86639(10) 0.0151(2) Uani 1 1 d . . . H2' H 0.3987 0.2015 0.8870 0.018 Uiso 1 1 calc R . . O2' O 0.07774(14) 0.20746(12) 0.89764(8) 0.02081(19) Uani 1 1 d . . . H2A H 0.060(3) 0.105(3) 0.8565(17) 0.029(4) Uiso 1 1 d . . . C3' C 0.28666(18) 0.46531(17) 0.93274(10) 0.0164(2) Uani 1 1 d . . . H3' H 0.2395 0.4560 1.0191 0.020 Uiso 1 1 calc R . . F3' F 0.49602(11) 0.53202(11) 0.92732(6) 0.02088(16) Uani 1 1 d . . . C4' C 0.13756(18) 0.58199(15) 0.85312(10) 0.0141(2) Uani 1 1 d . . . H4' H -0.0111 0.5626 0.8793 0.017 Uiso 1 1 calc R . . O4' O 0.15546(12) 0.51119(11) 0.72863(6) 0.01305(16) Uani 1 1 d . . . C5' C 0.18491(19) 0.78398(16) 0.85494(10) 0.0163(2) Uani 1 1 d . . . H5' H 0.1984 0.8268 0.9410 0.020 Uiso 1 1 calc R . . H5" H 0.3218 0.8065 0.8160 0.020 Uiso 1 1 calc R . . O5' O 0.01971(14) 0.88423(12) 0.79076(8) 0.01876(18) Uani 1 1 d . . . H5A H 0.036(3) 0.875(3) 0.716(2) 0.041(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0115(4) 0.0120(4) 0.0139(4) -0.0001(3) 0.0036(3) -0.0002(3) C2 0.0131(5) 0.0131(5) 0.0125(4) -0.0003(4) 0.0005(4) 0.0011(4) O2 0.0187(4) 0.0128(4) 0.0199(4) 0.0013(3) 0.0047(3) -0.0001(3) N3 0.0131(4) 0.0117(4) 0.0156(4) -0.0011(3) 0.0033(3) 0.0011(3) C4 0.0116(4) 0.0129(5) 0.0124(4) -0.0002(4) -0.0009(4) -0.0001(4) O4 0.0144(3) 0.0148(4) 0.0158(4) -0.0017(3) 0.0045(3) -0.0010(3) C5 0.0144(5) 0.0106(5) 0.0160(5) 0.0006(4) 0.0021(4) -0.0005(4) C6 0.0139(5) 0.0109(5) 0.0147(4) 0.0000(4) 0.0009(4) 0.0008(4) C1' 0.0108(4) 0.0111(4) 0.0139(5) -0.0002(4) 0.0031(3) 0.0005(4) C2' 0.0189(5) 0.0129(5) 0.0138(5) 0.0017(4) 0.0042(4) 0.0009(4) O2' 0.0270(4) 0.0140(4) 0.0225(4) -0.0018(3) 0.0139(3) -0.0043(3) C3' 0.0206(5) 0.0151(5) 0.0137(5) -0.0005(4) 0.0025(4) -0.0004(4) F3' 0.0201(3) 0.0226(4) 0.0196(3) -0.0020(3) -0.0042(2) -0.0017(3) C4' 0.0166(5) 0.0130(5) 0.0130(5) -0.0023(4) 0.0047(4) -0.0004(4) O4' 0.0139(3) 0.0135(4) 0.0119(3) -0.0014(3) 0.0019(3) 0.0032(3) C5' 0.0202(5) 0.0130(5) 0.0160(5) -0.0007(4) 0.0037(4) -0.0004(4) O5' 0.0257(4) 0.0145(4) 0.0163(4) 0.0000(3) 0.0026(3) 0.0027(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C6 1.3755(14) . ? N1 C2 1.3881(14) . ? N1 C1' 1.4939(12) . ? C2 O2 1.2201(14) . ? C2 N3 1.3899(13) . ? N3 C4 1.3818(14) . ? N3 H3 0.8800 . ? C4 O4 1.2457(13) . ? C4 C5 1.4363(14) . ? C5 C6 1.3437(14) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C1' O4' 1.4099(12) . ? C1' C2' 1.5357(14) . ? C1' H1' 1.0000 . ? C2' O2' 1.4151(13) . ? C2' C3' 1.5217(16) . ? C2' H2' 1.0000 . ? O2' H2A 0.88(2) . ? C3' F3' 1.4104(13) . ? C3' C4' 1.5178(16) . ? C3' H3' 1.0000 . ? C4' O4' 1.4613(12) . ? C4' C5' 1.5117(15) . ? C4' H4' 1.0000 . ? C5' O5' 1.4339(14) . ? C5' H5' 0.9900 . ? C5' H5" 0.9900 . ? O5' H5A 0.83(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 N1 C2 121.70(8) . . ? C6 N1 C1' 121.41(9) . . ? C2 N1 C1' 116.62(9) . . ? O2 C2 N1 122.69(9) . . ? O2 C2 N3 122.89(10) . . ? N1 C2 N3 114.41(9) . . ? C4 N3 C2 126.34(9) . . ? C4 N3 H3 116.8 . . ? C2 N3 H3 116.8 . . ? O4 C4 N3 119.91(9) . . ? O4 C4 C5 124.68(10) . . ? N3 C4 C5 115.41(9) . . ? C6 C5 C4 119.21(10) . . ? C6 C5 H5 120.4 . . ? C4 C5 H5 120.4 . . ? C5 C6 N1 122.55(10) . . ? C5 C6 H6 118.7 . . ? N1 C6 H6 118.7 . . ? O4' C1' N1 108.71(8) . . ? O4' C1' C2' 105.99(8) . . ? N1 C1' C2' 113.83(9) . . ? O4' C1' H1' 109.4 . . ? N1 C1' H1' 109.4 . . ? C2' C1' H1' 109.4 . . ? O2' C2' C3' 104.80(9) . . ? O2' C2' C1' 109.20(9) . . ? C3' C2' C1' 101.88(9) . . ? O2' C2' H2' 113.4 . . ? C3' C2' H2' 113.4 . . ? C1' C2' H2' 113.4 . . ? C2' O2' H2A 107.8(12) . . ? F3' C3' C4' 109.81(9) . . ? F3' C3' C2' 108.21(9) . . ? C4' C3' C2' 101.99(9) . . ? F3' C3' H3' 112.1 . . ? C4' C3' H3' 112.1 . . ? C2' C3' H3' 112.1 . . ? O4' C4' C5' 109.77(9) . . ? O4' C4' C3' 105.16(8) . . ? C5' C4' C3' 115.35(10) . . ? O4' C4' H4' 108.8 . . ? C5' C4' H4' 108.8 . . ? C3' C4' H4' 108.8 . . ? C1' O4' C4' 110.39(8) . . ? O5' C5' C4' 110.94(9) . . ? O5' C5' H5' 109.5 . . ? C4' C5' H5' 109.5 . . ? O5' C5' H5" 109.5 . . ? C4' C5' H5" 109.5 . . ? H5' C5' H5" 108.0 . . ? C5' O5' H5A 108.9(15) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 N1 C2 O2 176.33(10) . . . . ? C1' N1 C2 O2 -9.54(15) . . . . ? C6 N1 C2 N3 -4.67(14) . . . . ? C1' N1 C2 N3 169.45(8) . . . . ? O2 C2 N3 C4 179.31(10) . . . . ? N1 C2 N3 C4 0.32(15) . . . . ? C2 N3 C4 O4 -175.30(10) . . . . ? C2 N3 C4 C5 4.87(15) . . . . ? O4 C4 C5 C6 174.24(11) . . . . ? N3 C4 C5 C6 -5.94(14) . . . . ? C4 C5 C6 N1 2.07(16) . . . . ? C2 N1 C6 C5 3.59(16) . . . . ? C1' N1 C6 C5 -170.26(10) . . . . ? C6 N1 C1' O4' 9.80(13) . . . . ? C2 N1 C1' O4' -164.34(8) . . . . ? C6 N1 C1' C2' -108.07(11) . . . . ? C2 N1 C1' C2' 77.79(12) . . . . ? O4' C1' C2' O2' 79.48(10) . . . . ? N1 C1' C2' O2' -161.09(9) . . . . ? O4' C1' C2' C3' -30.98(11) . . . . ? N1 C1' C2' C3' 88.45(10) . . . . ? O2' C2' C3' F3' 167.99(8) . . . . ? C1' C2' C3' F3' -78.24(10) . . . . ? O2' C2' C3' C4' -76.25(10) . . . . ? C1' C2' C3' C4' 37.52(10) . . . . ? F3' C3' C4' O4' 82.99(10) . . . . ? C2' C3' C4' O4' -31.59(10) . . . . ? F3' C3' C4' C5' -38.09(12) . . . . ? C2' C3' C4' C5' -152.67(9) . . . . ? N1 C1' O4' C4' -111.16(9) . . . . ? C2' C1' O4' C4' 11.58(10) . . . . ? C5' C4' O4' C1' 137.42(9) . . . . ? C3' C4' O4' C1' 12.76(10) . . . . ? O4' C4' C5' O5' 69.33(11) . . . . ? C3' C4' C5' O5' -172.13(9) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.271 _refine_diff_density_min -0.174 _refine_diff_density_rms 0.040 #===END