data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Jonathan Percy' 'Andrea Arany' 'Patrick J. Crowley' 'John Fawcett' 'Michael B. Hursthouse' 'Benson M. Kariuki' 'Mark E. Light' 'Andrew C. Moralee' 'Vittoria Salafia' _publ_contact_author_name 'Prof Jonathan Percy' _publ_contact_author_address ; Department of Chemistry University of Leicester University Road Leicester LE1 7RH UNITED KINGDOM ; _publ_contact_author_email JMP29@LE.AC.UK _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; Highly-functionalised Difluorinated (Hydroxymethyl)conduritol Analogues via the Diels-Alder Reactions of a Difluorinated Dienophile ; _publ_section_references ; PLATON- (a) Spek, A. L. (1990) Acta Cryst. A46, C34. (b) Spek, A. L. (1998) PLATON, A Multipurpose Crystallographic Tool, Utrecht University, Utrecht, The Netherlands. SHELXTL, program suite for structure solution and refinement, Bruker AXS, Inc. 5465 East Cheryl Parkway, Nadison, Wisconsin 53711-5373, USA SMART, program for instrument control and data aquisition, Bruker AXS, Inc. 5465 East Cheryl Parkway, Nadison, Wisconsin 53711-5373, USA SAINTPLUS, program suite for data processing, Bruker AXS, Inc. 5465 East Cheryl Parkway, Nadison, Wisconsin 53711-5373, USA ; data_12a _database_code_depnum_ccdc_archive 'CCDC 224031' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H19 F2 N O5' _chemical_formula_weight 319.30 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' F F 0.0171 0.0103 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 16.3285(16) _cell_length_b 11.9385(11) _cell_length_c 17.5557(13) _cell_angle_alpha 90.00 _cell_angle_beta 116.70(4) _cell_angle_gamma 90.00 _cell_volume 3057.4(5) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 351739 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.387 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1344 _exptl_absorpt_coefficient_mu 0.120 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9764 _exptl_absorpt_correction_T_max 0.9822 _exptl_absorpt_process_details 'SORTAV (Blessing, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Bruker Nonius Kappa CCD Area detector' _diffrn_measurement_method '\f and \w scans to fill the asymmetric unit' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 37999 _diffrn_reflns_av_R_equivalents 0.1526 _diffrn_reflns_av_sigmaI/netI 0.0940 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 24.95 _reflns_number_total 5330 _reflns_number_gt 2669 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO (Otwinowski and MInor, 1997)' _computing_data_reduction 'DENZO, COLLECT, MAXUS (Mackay et al., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0799P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5330 _refine_ls_number_parameters 403 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1446 _refine_ls_R_factor_gt 0.0595 _refine_ls_wR_factor_ref 0.1588 _refine_ls_wR_factor_gt 0.1250 _refine_ls_goodness_of_fit_ref 0.939 _refine_ls_restrained_S_all 0.939 _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 F1 F 0.94137(13) 1.08522(15) 0.62695(11) 0.0435(5) Uani 1 1 d . . . F2 F 0.91385(13) 1.06983(15) 0.73634(11) 0.0411(5) Uani 1 1 d . . . N1 N 0.84834(18) 0.7804(2) 0.46529(15) 0.0340(7) Uani 1 1 d . . . O1 O 1.08443(15) 0.91950(19) 0.71401(13) 0.0386(6) Uani 1 1 d . . . O2 O 0.86207(16) 0.8060(2) 0.75256(13) 0.0409(6) Uani 1 1 d . . . O3 O 0.77384(15) 0.90378(19) 0.63416(13) 0.0363(6) Uani 1 1 d . . . O4 O 0.90532(15) 0.88655(18) 0.58310(12) 0.0319(6) Uani 1 1 d . . . O5 O 0.86162(16) 0.70804(18) 0.59018(13) 0.0378(6) Uani 1 1 d . . . C1 C 0.9306(2) 0.8959(3) 0.67196(18) 0.0300(8) Uani 1 1 d . . . C2 C 0.9603(2) 1.0207(3) 0.6965(2) 0.0339(9) Uani 1 1 d . . . C3 C 1.0630(2) 1.0116(3) 0.7545(2) 0.0373(9) Uani 1 1 d . . . H3 H 1.0983 1.0802 0.7604 0.045 Uiso 1 1 calc R . . C4 C 1.0732(2) 0.9613(3) 0.8367(2) 0.0385(9) Uani 1 1 d . . . H4 H 1.0924 0.9973 0.8888 0.046 Uiso 1 1 calc R . . C5 C 1.0492(2) 0.8551(3) 0.81945(19) 0.0359(9) Uani 1 1 d . . . H5 H 1.0478 0.8011 0.8570 0.043 Uiso 1 1 calc R . . C6 C 1.0245(2) 0.8391(3) 0.72572(19) 0.0331(8) Uani 1 1 d . . . H6 H 1.0298 0.7621 0.7091 0.040 Uiso 1 1 calc R . . C7 C 0.8522(2) 0.8606(3) 0.6914(2) 0.0324(8) Uani 1 1 d . . . C8 C 0.6931(2) 0.8818(3) 0.6463(2) 0.0438(10) Uani 1 1 d . . . H8A H 0.6914 0.9321 0.6890 0.053 Uiso 1 1 calc R . . H8B H 0.6943 0.8054 0.6656 0.053 Uiso 1 1 calc R . . C9 C 0.6110(3) 0.8997(4) 0.5629(2) 0.0665(13) Uani 1 1 d . . . H9A H 0.6115 0.9748 0.5436 0.100 Uiso 1 1 calc R . . H9B H 0.5564 0.8882 0.5696 0.100 Uiso 1 1 calc R . . H9C H 0.6121 0.8476 0.5217 0.100 Uiso 1 1 calc R . . C10 C 0.8702(2) 0.7838(3) 0.5479(2) 0.0316(8) Uani 1 1 d . . . C11 C 0.8079(3) 0.6765(3) 0.4192(2) 0.0434(10) Uani 1 1 d . . . H11C H 0.7709 0.6937 0.3593 0.052 Uiso 1 1 calc R . . H11D H 0.7676 0.6453 0.4409 0.052 Uiso 1 1 calc R . . C12 C 0.8786(3) 0.5902(3) 0.4274(2) 0.0623(13) Uani 1 1 d . . . H12D H 0.9157 0.6183 0.4020 0.093 Uiso 1 1 calc R . . H12E H 0.8484 0.5227 0.3988 0.093 Uiso 1 1 calc R . . H12F H 0.9167 0.5745 0.4866 0.093 Uiso 1 1 calc R . . C13 C 0.8637(2) 0.8734(3) 0.4185(2) 0.0412(9) Uani 1 1 d . . . H13C H 0.8805 0.8435 0.3761 0.049 Uiso 1 1 calc R . . H13D H 0.9143 0.9188 0.4578 0.049 Uiso 1 1 calc R . . C14 C 0.7794(3) 0.9463(3) 0.3748(2) 0.0634(12) Uani 1 1 d . . . H14D H 0.7287 0.9011 0.3372 0.095 Uiso 1 1 calc R . . H14E H 0.7910 1.0037 0.3426 0.095 Uiso 1 1 calc R . . H14F H 0.7651 0.9802 0.4170 0.095 Uiso 1 1 calc R . . F1A F 0.44062(14) 0.58667(15) 0.13856(11) 0.0425(5) Uani 1 1 d . . . F2A F 0.40651(13) 0.60603(15) 0.24352(12) 0.0424(5) Uani 1 1 d . . . N1A N 0.35333(18) 0.8826(2) -0.02923(15) 0.0326(7) Uani 1 1 d . . . O1A O 0.58276(15) 0.75275(19) 0.22945(13) 0.0363(6) Uani 1 1 d . . . O2A O 0.35226(16) 0.8674(2) 0.25415(14) 0.0423(6) Uani 1 1 d . . . O3A O 0.27050(15) 0.76786(19) 0.13437(13) 0.0370(6) Uani 1 1 d . . . O4A O 0.40773(15) 0.78414(17) 0.09187(12) 0.0320(6) Uani 1 1 d . . . O5A O 0.36811(16) 0.96616(18) 0.09341(13) 0.0376(6) Uani 1 1 d . . . C1A C 0.4282(2) 0.7778(3) 0.17981(18) 0.0296(8) Uani 1 1 d . . . C2A C 0.4554(2) 0.6527(3) 0.2059(2) 0.0333(9) Uani 1 1 d . . . C3A C 0.5588(2) 0.6610(3) 0.26846(19) 0.0364(9) Uani 1 1 d . . . H3A H 0.5945 0.5922 0.2767 0.044 Uiso 1 1 calc R . . C4A C 0.5635(2) 0.7147(3) 0.34878(19) 0.0366(9) Uani 1 1 d . . . H4A H 0.5791 0.6802 0.4010 0.044 Uiso 1 1 calc R . . C5A C 0.5411(2) 0.8197(3) 0.32896(19) 0.0361(9) Uani 1 1 d . . . H5A H 0.5379 0.8751 0.3648 0.043 Uiso 1 1 calc R . . C6A C 0.5214(2) 0.8338(3) 0.23704(19) 0.0325(8) Uani 1 1 d . . . H6A H 0.5283 0.9103 0.2206 0.039 Uiso 1 1 calc R . . C7A C 0.3472(2) 0.8125(3) 0.1947(2) 0.0320(8) Uani 1 1 d . . . C8A C 0.1880(2) 0.7792(3) 0.1454(2) 0.0448(10) Uani 1 1 d . . . H8A1 H 0.1836 0.8544 0.1642 0.054 Uiso 1 1 calc R . . H8A2 H 0.1889 0.7264 0.1878 0.054 Uiso 1 1 calc R . . C9A C 0.1085(3) 0.7557(4) 0.0607(2) 0.0646(13) Uani 1 1 d . . . H9A1 H 0.1095 0.8070 0.0190 0.097 Uiso 1 1 calc R . . H9A2 H 0.0523 0.7647 0.0650 0.097 Uiso 1 1 calc R . . H9A3 H 0.1127 0.6803 0.0437 0.097 Uiso 1 1 calc R . . C10A C 0.3744(2) 0.8864(3) 0.0532(2) 0.0318(8) Uani 1 1 d . . . C11A C 0.3141(2) 0.9828(3) -0.0811(2) 0.0404(9) Uani 1 1 d . . . H11A H 0.2845 1.0279 -0.0546 0.048 Uiso 1 1 calc R . . H11B H 0.2677 0.9604 -0.1370 0.048 Uiso 1 1 calc R . . C12A C 0.3860(3) 1.0524(3) -0.0910(2) 0.0554(11) Uani 1 1 d . . . H12A H 0.4273 1.0834 -0.0368 0.083 Uiso 1 1 calc R . . H12B H 0.3568 1.1120 -0.1307 0.083 Uiso 1 1 calc R . . H12C H 0.4196 1.0060 -0.1119 0.083 Uiso 1 1 calc R . . C13A C 0.3601(2) 0.7801(3) -0.0722(2) 0.0413(9) Uani 1 1 d . . . H13A H 0.4140 0.7385 -0.0341 0.050 Uiso 1 1 calc R . . H13B H 0.3677 0.8003 -0.1222 0.050 Uiso 1 1 calc R . . C14A C 0.2765(3) 0.7057(3) -0.0992(2) 0.0502(10) Uani 1 1 d . . . H14A H 0.2715 0.6804 -0.0495 0.075 Uiso 1 1 calc R . . H14B H 0.2825 0.6422 -0.1299 0.075 Uiso 1 1 calc R . . H14C H 0.2226 0.7473 -0.1352 0.075 Uiso 1 1 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_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.0520(14) 0.0296(12) 0.0429(11) 0.0075(9) 0.0162(10) -0.0012(10) F2 0.0397(12) 0.0330(12) 0.0493(12) -0.0085(9) 0.0187(10) 0.0021(9) N1 0.0397(18) 0.0375(19) 0.0226(15) -0.0011(13) 0.0120(14) -0.0028(15) O1 0.0369(15) 0.0358(15) 0.0428(13) -0.0036(11) 0.0176(12) 0.0011(12) O2 0.0466(16) 0.0454(16) 0.0304(13) 0.0041(12) 0.0170(12) -0.0055(13) O3 0.0315(15) 0.0395(15) 0.0367(13) 0.0048(11) 0.0144(12) 0.0012(12) O4 0.0377(14) 0.0300(14) 0.0271(12) -0.0012(10) 0.0138(11) -0.0028(11) O5 0.0490(16) 0.0293(14) 0.0344(13) 0.0016(11) 0.0182(12) -0.0023(12) C1 0.034(2) 0.031(2) 0.0243(17) -0.0010(15) 0.0117(16) 0.0017(16) C2 0.039(2) 0.027(2) 0.039(2) 0.0010(17) 0.0208(19) 0.0033(17) C3 0.038(2) 0.030(2) 0.041(2) -0.0078(17) 0.0150(18) -0.0026(17) C4 0.036(2) 0.040(2) 0.0331(19) -0.0072(17) 0.0103(18) -0.0009(19) C5 0.034(2) 0.040(2) 0.0296(18) 0.0034(17) 0.0103(17) 0.0021(18) C6 0.033(2) 0.027(2) 0.0363(19) -0.0016(15) 0.0133(17) -0.0013(16) C7 0.040(2) 0.028(2) 0.0286(19) -0.0044(16) 0.0143(18) -0.0030(18) C8 0.036(2) 0.053(3) 0.043(2) -0.0052(18) 0.0180(19) -0.007(2) C9 0.035(3) 0.101(4) 0.055(2) 0.008(2) 0.012(2) -0.007(2) C10 0.027(2) 0.030(2) 0.034(2) -0.0005(17) 0.0103(16) -0.0003(17) C11 0.052(3) 0.044(2) 0.0289(19) -0.0047(17) 0.0133(19) -0.010(2) C12 0.089(4) 0.048(3) 0.045(2) -0.006(2) 0.026(2) 0.010(2) C13 0.042(2) 0.052(3) 0.0311(19) 0.0018(18) 0.0180(18) -0.004(2) C14 0.056(3) 0.048(3) 0.067(3) 0.024(2) 0.011(2) -0.004(2) F1A 0.0536(14) 0.0274(11) 0.0405(11) -0.0027(9) 0.0160(10) 0.0007(10) F2A 0.0462(13) 0.0346(12) 0.0476(12) 0.0077(9) 0.0222(11) -0.0028(10) N1A 0.0364(18) 0.0332(18) 0.0228(14) 0.0009(13) 0.0087(13) -0.0005(14) O1A 0.0304(14) 0.0356(15) 0.0408(13) 0.0042(11) 0.0141(11) -0.0003(11) O2A 0.0475(16) 0.0454(16) 0.0358(14) -0.0022(12) 0.0202(12) 0.0034(13) O3A 0.0322(15) 0.0386(15) 0.0374(13) -0.0024(11) 0.0132(12) -0.0037(12) O4A 0.0398(15) 0.0274(14) 0.0271(12) -0.0003(10) 0.0136(11) -0.0007(11) O5A 0.0474(16) 0.0278(14) 0.0332(13) -0.0034(11) 0.0142(12) 0.0028(12) C1A 0.036(2) 0.025(2) 0.0267(17) 0.0027(15) 0.0136(16) 0.0000(17) C2A 0.041(2) 0.028(2) 0.0319(19) -0.0008(16) 0.0175(18) -0.0045(17) C3A 0.040(2) 0.028(2) 0.038(2) 0.0077(16) 0.0143(18) 0.0032(17) C4A 0.032(2) 0.043(2) 0.0275(18) 0.0093(17) 0.0066(16) -0.0023(19) C5A 0.037(2) 0.032(2) 0.0298(18) 0.0002(16) 0.0057(17) -0.0024(17) C6A 0.036(2) 0.023(2) 0.0352(19) 0.0022(15) 0.0138(17) 0.0005(16) C7A 0.038(2) 0.026(2) 0.0297(19) 0.0041(16) 0.0137(18) -0.0007(17) C8A 0.036(2) 0.049(3) 0.048(2) 0.0093(19) 0.019(2) 0.0030(19) C9A 0.033(3) 0.096(4) 0.055(2) 0.013(3) 0.011(2) -0.002(2) C10A 0.031(2) 0.026(2) 0.035(2) 0.0035(17) 0.0123(17) -0.0023(16) C11A 0.048(2) 0.035(2) 0.0308(19) 0.0053(16) 0.0109(18) 0.0000(18) C12A 0.072(3) 0.043(3) 0.055(2) 0.015(2) 0.032(2) 0.001(2) C13A 0.042(2) 0.050(3) 0.0306(19) -0.0033(17) 0.0152(18) 0.000(2) C14A 0.048(3) 0.047(3) 0.052(2) -0.0117(19) 0.019(2) -0.008(2) _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 F1 C2 1.356(3) . ? F2 C2 1.373(3) . ? N1 C10 1.329(4) . ? N1 C11 1.466(4) . ? N1 C13 1.468(4) . ? O1 C3 1.436(4) . ? O1 C6 1.449(4) . ? O2 C7 1.203(4) . ? O3 C7 1.325(4) . ? O3 C8 1.451(4) . ? O4 C10 1.377(4) . ? O4 C1 1.427(3) . ? O5 C10 1.218(4) . ? C1 C7 1.525(4) . ? C1 C6 1.550(4) . ? C1 C2 1.567(4) . ? C2 C3 1.525(5) . ? C3 C4 1.500(4) . ? C4 C5 1.321(5) . ? C5 C6 1.520(4) . ? C8 C9 1.492(5) . ? C11 C12 1.505(5) . ? C13 C14 1.513(5) . ? F1A C2A 1.348(3) . ? F2A C2A 1.364(3) . ? N1A C10A 1.330(4) . ? N1A C11A 1.464(4) . ? N1A C13A 1.468(4) . ? O1A C3A 1.436(4) . ? O1A C6A 1.441(4) . ? O2A C7A 1.204(3) . ? O3A C7A 1.334(4) . ? O3A C8A 1.451(4) . ? O4A C10A 1.385(4) . ? O4A C1A 1.427(3) . ? O5A C10A 1.216(4) . ? C1A C7A 1.517(4) . ? C1A C6A 1.548(4) . ? C1A C2A 1.567(4) . ? C2A C3A 1.549(5) . ? C3A C4A 1.519(4) . ? C4A C5A 1.309(5) . ? C5A C6A 1.506(4) . ? C8A C9A 1.497(5) . ? C11A C12A 1.511(5) . ? C13A C14A 1.515(5) . ? 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 C10 N1 C11 117.5(3) . . ? C10 N1 C13 123.9(3) . . ? C11 N1 C13 118.6(2) . . ? C3 O1 C6 96.1(2) . . ? C7 O3 C8 116.7(3) . . ? C10 O4 C1 114.7(2) . . ? O4 C1 C7 111.4(3) . . ? O4 C1 C6 110.6(2) . . ? C7 C1 C6 116.3(3) . . ? O4 C1 C2 106.0(2) . . ? C7 C1 C2 112.8(3) . . ? C6 C1 C2 98.5(3) . . ? F1 C2 F2 105.2(3) . . ? F1 C2 C3 112.3(3) . . ? F2 C2 C3 112.5(3) . . ? F1 C2 C1 112.0(2) . . ? F2 C2 C1 111.8(3) . . ? C3 C2 C1 103.2(3) . . ? O1 C3 C4 102.9(3) . . ? O1 C3 C2 99.4(2) . . ? C4 C3 C2 106.6(3) . . ? C5 C4 C3 105.7(3) . . ? C4 C5 C6 106.0(3) . . ? O1 C6 C5 101.7(3) . . ? O1 C6 C1 99.8(2) . . ? C5 C6 C1 108.3(3) . . ? O2 C7 O3 125.8(3) . . ? O2 C7 C1 124.0(3) . . ? O3 C7 C1 110.1(3) . . ? O3 C8 C9 107.7(3) . . ? O5 C10 N1 126.5(3) . . ? O5 C10 O4 121.7(3) . . ? N1 C10 O4 111.8(3) . . ? N1 C11 C12 113.0(3) . . ? N1 C13 C14 111.9(3) . . ? C10A N1A C11A 118.4(3) . . ? C10A N1A C13A 123.1(3) . . ? C11A N1A C13A 118.3(2) . . ? C3A O1A C6A 96.8(2) . . ? C7A O3A C8A 116.9(2) . . ? C10A O4A C1A 115.2(2) . . ? O4A C1A C7A 111.9(3) . . ? O4A C1A C6A 111.3(2) . . ? C7A C1A C6A 116.7(3) . . ? O4A C1A C2A 105.3(2) . . ? C7A C1A C2A 111.4(3) . . ? C6A C1A C2A 98.9(3) . . ? F1A C2A F2A 105.8(3) . . ? F1A C2A C3A 111.6(3) . . ? F2A C2A C3A 111.8(2) . . ? F1A C2A C1A 112.7(2) . . ? F2A C2A C1A 112.3(3) . . ? C3A C2A C1A 102.8(3) . . ? O1A C3A C4A 102.1(3) . . ? O1A C3A C2A 98.9(2) . . ? C4A C3A C2A 105.7(3) . . ? C5A C4A C3A 105.4(3) . . ? C4A C5A C6A 106.9(3) . . ? O1A C6A C5A 101.6(3) . . ? O1A C6A C1A 99.9(2) . . ? C5A C6A C1A 108.8(3) . . ? O2A C7A O3A 125.5(3) . . ? O2A C7A C1A 124.9(3) . . ? O3A C7A C1A 109.5(3) . . ? O3A C8A C9A 107.0(3) . . ? O5A C10A N1A 127.6(3) . . ? O5A C10A O4A 121.5(3) . . ? N1A C10A O4A 110.8(3) . . ? N1A C11A C12A 112.0(3) . . ? N1A C13A C14A 112.6(3) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 24.95 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.530 _refine_diff_density_min -0.254 _refine_diff_density_rms 0.065 #===END data_13b _database_code_depnum_ccdc_archive 'CCDC 224032' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H21 F2 N O5' _chemical_formula_weight 333.33 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.951(4) _cell_length_b 8.869(5) _cell_length_c 13.399(7) _cell_angle_alpha 98.346(10) _cell_angle_beta 96.497(9) _cell_angle_gamma 91.913(10) _cell_volume 811.0(8) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 533 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 18.47 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.365 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 352 _exptl_absorpt_coefficient_mu 0.116 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5929 _diffrn_reflns_av_R_equivalents 0.1077 _diffrn_reflns_av_sigmaI/netI 0.1633 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2833 _reflns_number_gt 1140 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0598P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2833 _refine_ls_number_parameters 237 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1780 _refine_ls_R_factor_gt 0.0718 _refine_ls_wR_factor_ref 0.1912 _refine_ls_wR_factor_gt 0.1506 _refine_ls_goodness_of_fit_ref 0.887 _refine_ls_restrained_S_all 0.887 _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 F1 F 0.4924(4) 0.7849(3) 0.9204(2) 0.0670(9) Uani 1 1 d . C . F2 F 0.4071(4) 0.9717(3) 0.8438(2) 0.0650(9) Uani 1 1 d . C . N1 N 0.4590(7) 0.4202(5) 0.7724(4) 0.0768(16) Uani 1 1 d . . . O1 O 0.8137(5) 1.0081(4) 0.8204(3) 0.0565(10) Uani 1 1 d . C . O2 O 0.4676(5) 0.9526(5) 0.6514(3) 0.0739(12) Uani 1 1 d . C . O3 O 0.5202(6) 0.7123(4) 0.5900(3) 0.0773(13) Uani 1 1 d . B . O4 O 0.6209(5) 0.6333(4) 0.7627(2) 0.0481(9) Uani 1 1 d . . . O5 O 0.2955(5) 0.6274(4) 0.7417(3) 0.0760(13) Uani 1 1 d . . . C1 C 0.8393(8) 0.8571(6) 0.7754(4) 0.0552(15) Uani 1 1 d . . . C2 C 0.6207(7) 0.7918(6) 0.7605(4) 0.0452(13) Uani 1 1 d . C . C3 C 0.5574(8) 0.8830(6) 0.8601(4) 0.0498(14) Uani 1 1 d . . . C4 C 0.7356(8) 0.9732(6) 0.9079(4) 0.0593(15) Uani 1 1 d . C . H4 H 0.7152 1.0631 0.9593 0.071 Uiso 1 1 calc R . . C5 C 0.8738(8) 0.8605(6) 0.9451(4) 0.0628(16) Uani 1 1 d . . . H5 H 0.9083 0.8448 1.0133 0.075 Uiso 1 1 calc R C . C6 C 0.9359(8) 0.7891(6) 0.8641(4) 0.0572(15) Uani 1 1 d . C . H6 H 1.0246 0.7098 0.8612 0.069 Uiso 1 1 calc R . . C7 C 0.9366(8) 0.8469(6) 0.6825(4) 0.0759(18) Uani 1 1 d . C . H7A H 0.8623 0.8996 0.6326 0.114 Uiso 1 1 calc R . . H7B H 0.9445 0.7394 0.6539 0.114 Uiso 1 1 calc R . . H7C H 1.0676 0.8948 0.6993 0.114 Uiso 1 1 calc R . . C8 C 0.5194(7) 0.8290(7) 0.6628(4) 0.0534(14) Uani 1 1 d . . . C9 C 0.4418(13) 0.7351(10) 0.4878(5) 0.126(3) Uani 1 1 d . . . H9A H 0.5008 0.8306 0.4720 0.151 Uiso 1 1 calc R A 1 H9B H 0.4769 0.6497 0.4381 0.151 Uiso 1 1 calc R A 1 C10 C 0.247(3) 0.7431(19) 0.4782(17) 0.089(6) Uani 0.50 1 d P B 1 H10A H 0.1873 0.6464 0.4898 0.133 Uiso 0.50 1 d PR B 1 H10B H 0.2008 0.7625 0.4096 0.133 Uiso 0.50 1 d PR B 1 H10C H 0.2112 0.8262 0.5282 0.133 Uiso 0.50 1 d PR B 1 C10' C 0.230(3) 0.627(2) 0.4713(16) 0.134(10) Uani 0.50 1 d P B 2 H10D H 0.1401 0.6762 0.5156 0.201 Uiso 0.50 1 d PR B 2 H10E H 0.2560 0.5257 0.4886 0.201 Uiso 0.50 1 d PR B 2 H10F H 0.1726 0.6179 0.4003 0.201 Uiso 0.50 1 d PR B 2 C11 C 0.4424(9) 0.5620(6) 0.7575(4) 0.0592(15) Uani 1 1 d . C . C12 C 0.6411(8) 0.3531(6) 0.7997(4) 0.0648(17) Uani 1 1 d . C . H12A H 0.7397 0.3881 0.7592 0.078 Uiso 1 1 calc R . . H12B H 0.6241 0.2407 0.7828 0.078 Uiso 1 1 calc R . . C13 C 0.7122(9) 0.3946(7) 0.9101(5) 0.083(2) Uani 1 1 d . . . H13A H 0.7385 0.5053 0.9263 0.125 Uiso 1 1 calc R C . H13B H 0.8316 0.3426 0.9260 0.125 Uiso 1 1 calc R . . H13C H 0.6133 0.3632 0.9506 0.125 Uiso 1 1 calc R . . C14 C 0.279(4) 0.340(3) 0.795(2) 0.076(6) Uani 0.50 1 d P C 1 H14A H 0.3153 0.2737 0.8466 0.091 Uiso 0.50 1 calc PR C 1 H14B H 0.1930 0.4170 0.8239 0.091 Uiso 0.50 1 calc PR C 1 C15 C 0.175(2) 0.2501(16) 0.7088(15) 0.095(7) Uani 0.50 1 d P C 1 H15A H 0.1620 0.3082 0.6518 0.142 Uiso 0.50 1 d PR C 1 H15B H 0.0459 0.2217 0.7251 0.142 Uiso 0.50 1 d PR C 1 H15C H 0.2442 0.1576 0.6902 0.142 Uiso 0.50 1 d PR C 1 C14' C 0.283(3) 0.312(2) 0.7306(14) 0.078(6) Uani 0.50 1 d P C 2 H14C H 0.1959 0.3517 0.6781 0.093 Uiso 0.50 1 calc PR C 2 H14D H 0.3204 0.2078 0.7043 0.093 Uiso 0.50 1 calc PR C 2 C15' C 0.203(4) 0.318(3) 0.827(2) 0.089(7) Uani 0.50 1 d P C 2 H15D H 0.3002 0.2883 0.8782 0.134 Uiso 0.50 1 d PR C 2 H15E H 0.0885 0.2484 0.8177 0.134 Uiso 0.50 1 d PR C 2 H15F H 0.1666 0.4226 0.8489 0.134 Uiso 0.50 1 d PR C 2 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 F1 0.071(2) 0.066(2) 0.071(2) 0.0221(17) 0.0243(17) 0.0119(17) F2 0.058(2) 0.065(2) 0.076(2) 0.0133(17) 0.0135(16) 0.0262(16) N1 0.046(3) 0.042(3) 0.144(5) 0.028(3) -0.001(3) 0.003(3) O1 0.053(2) 0.045(2) 0.075(3) 0.0155(19) 0.011(2) 0.0071(18) O2 0.082(3) 0.085(3) 0.062(3) 0.032(2) 0.008(2) 0.038(2) O3 0.104(3) 0.079(3) 0.046(2) 0.008(2) -0.003(2) 0.025(3) O4 0.042(2) 0.044(2) 0.059(2) 0.0115(17) 0.0022(17) 0.0060(17) O5 0.046(2) 0.058(3) 0.128(4) 0.031(2) 0.004(2) 0.018(2) C1 0.055(4) 0.051(4) 0.061(4) 0.012(3) 0.004(3) 0.016(3) C2 0.042(3) 0.047(3) 0.049(3) 0.016(3) -0.001(3) 0.008(3) C3 0.052(4) 0.042(3) 0.063(4) 0.023(3) 0.016(3) 0.016(3) C4 0.059(4) 0.057(4) 0.062(4) 0.006(3) 0.007(3) 0.006(3) C5 0.065(4) 0.064(4) 0.059(4) 0.013(3) -0.004(3) 0.021(3) C6 0.054(4) 0.048(3) 0.067(4) 0.012(3) -0.012(3) 0.006(3) C7 0.065(4) 0.086(5) 0.089(5) 0.030(4) 0.035(4) 0.028(3) C8 0.047(3) 0.060(4) 0.056(4) 0.015(3) 0.006(3) 0.011(3) C9 0.154(8) 0.173(9) 0.050(5) 0.019(5) -0.010(5) 0.063(7) C10 0.065(11) 0.124(16) 0.071(11) -0.005(12) -0.001(8) 0.014(13) C10' 0.080(13) 0.24(3) 0.055(10) -0.027(19) -0.034(8) 0.03(2) C11 0.053(4) 0.044(4) 0.079(4) 0.008(3) 0.002(3) 0.007(3) C12 0.060(4) 0.048(4) 0.090(5) 0.017(3) 0.008(3) 0.021(3) C13 0.093(5) 0.079(5) 0.087(5) 0.038(4) 0.016(4) 0.018(4) C14 0.080(18) 0.058(12) 0.10(2) 0.033(14) 0.028(17) 0.028(13) C15 0.047(10) 0.054(10) 0.17(2) -0.001(10) -0.032(10) 0.004(7) C14' 0.095(15) 0.083(13) 0.046(10) -0.014(10) -0.002(13) 0.001(10) C15' 0.10(2) 0.084(14) 0.094(18) 0.037(12) 0.026(13) 0.032(14) _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 F1 C3 1.369(5) . ? F2 C3 1.346(5) . ? N1 C11 1.309(6) . ? N1 C12 1.449(6) . ? N1 C14 1.50(2) . ? N1 C14' 1.53(2) . ? O1 C1 1.412(5) . ? O1 C4 1.416(6) . ? O2 C8 1.190(6) . ? O3 C8 1.315(6) . ? O3 C9 1.460(6) . ? O4 C11 1.364(6) . ? O4 C2 1.410(5) . ? O5 C11 1.204(6) . ? C1 C7 1.475(7) . ? C1 C6 1.511(7) . ? C1 C2 1.588(7) . ? C2 C8 1.500(7) . ? C2 C3 1.572(7) . ? C3 C4 1.480(7) . ? C4 C5 1.507(7) . ? C5 C6 1.300(7) . ? C9 C10 1.35(2) . ? C9 C10' 1.70(2) . ? C12 C13 1.494(7) . ? C14 C15 1.41(4) . ? C14' C15' 1.45(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 C11 N1 C12 124.5(5) . . ? C11 N1 C14 116.0(10) . . ? C12 N1 C14 116.6(10) . . ? C11 N1 C14' 115.8(9) . . ? C12 N1 C14' 117.6(8) . . ? C14 N1 C14' 33.1(11) . . ? C1 O1 C4 97.8(4) . . ? C8 O3 C9 116.8(5) . . ? C11 O4 C2 115.2(4) . . ? O1 C1 C7 113.9(5) . . ? O1 C1 C6 102.0(4) . . ? C7 C1 C6 117.9(5) . . ? O1 C1 C2 99.6(4) . . ? C7 C1 C2 115.9(4) . . ? C6 C1 C2 105.1(4) . . ? O4 C2 C8 112.3(4) . . ? O4 C2 C3 112.5(4) . . ? C8 C2 C3 115.5(4) . . ? O4 C2 C1 108.2(4) . . ? C8 C2 C1 109.6(4) . . ? C3 C2 C1 97.4(4) . . ? F2 C3 F1 103.9(4) . . ? F2 C3 C4 112.1(4) . . ? F1 C3 C4 112.7(4) . . ? F2 C3 C2 114.1(4) . . ? F1 C3 C2 110.5(4) . . ? C4 C3 C2 103.7(4) . . ? O1 C4 C3 100.3(4) . . ? O1 C4 C5 102.4(4) . . ? C3 C4 C5 106.2(4) . . ? C6 C5 C4 105.5(5) . . ? C5 C6 C1 106.5(5) . . ? O2 C8 O3 125.5(5) . . ? O2 C8 C2 123.9(5) . . ? O3 C8 C2 110.1(5) . . ? C10 C9 O3 112.0(11) . . ? C10 C9 C10' 36.8(10) . . ? O3 C9 C10' 101.1(9) . . ? O5 C11 N1 127.7(6) . . ? O5 C11 O4 121.9(5) . . ? N1 C11 O4 110.4(5) . . ? N1 C12 C13 112.2(5) . . ? C15 C14 N1 114(2) . . ? C15' C14' N1 95.5(19) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.372 _refine_diff_density_min -0.201 _refine_diff_density_rms 0.050 #===END data_14b _database_code_depnum_ccdc_archive 'CCDC 224033' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H23 F2 N O5' _chemical_formula_sum 'C16 H23 F2 N O5' _chemical_formula_weight 347.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables 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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.8012(5) _cell_length_b 8.9989(5) _cell_length_c 14.1190(9) _cell_angle_alpha 96.881(3) _cell_angle_beta 102.152(3) _cell_angle_gamma 108.900(3) _cell_volume 897.60(10) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1709 _cell_measurement_theta_min 3.27 _cell_measurement_theta_max 55.17 _exptl_crystal_description plate _exptl_crystal_colour clear _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.285 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 368 _exptl_absorpt_coefficient_mu 0.923 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6554 _exptl_absorpt_correction_T_max 0.9134 _exptl_absorpt_process_details 'SADABS in SAINTPLUS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart 6000 CCD' _diffrn_measurement_method 'CCD scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4530 _diffrn_reflns_av_R_equivalents 0.0332 _diffrn_reflns_av_sigmaI/netI 0.0279 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _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 3.27 _diffrn_reflns_theta_max 55.17 _reflns_number_total 2041 _reflns_number_gt 1709 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement SAINTPLUS _computing_data_reduction SAINTPLUS _computing_structure_solution SHELXTL _computing_structure_refinement SHELXTL _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0992P)^2^+0.3578P] 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 SHELXL _refine_ls_extinction_coef 0.0052(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2041 _refine_ls_number_parameters 223 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0638 _refine_ls_R_factor_gt 0.0563 _refine_ls_wR_factor_ref 0.1693 _refine_ls_wR_factor_gt 0.1632 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_restrained_S_all 1.080 _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 C1 C 0.2485(4) 0.8299(3) 0.7076(2) 0.0548(8) Uani 1 1 d . . . C2 C 0.0435(5) 0.7912(4) 0.6432(3) 0.0662(10) Uani 1 1 d . . . C3 C 0.0724(5) 0.8409(4) 0.5475(3) 0.0719(10) Uani 1 1 d . . . H3 H -0.0355 0.8548 0.5048 0.086 Uiso 1 1 calc R . . C4 C 0.1524(5) 0.7339(4) 0.4990(3) 0.0756(10) Uani 1 1 d . . . H4 H 0.0905 0.6536 0.4425 0.091 Uiso 1 1 calc R . . C5 C 0.3288(5) 0.7741(4) 0.5513(2) 0.0670(10) Uani 1 1 d . . . C6 C 0.3595(5) 0.9102(4) 0.6349(2) 0.0621(9) Uani 1 1 d . . . C7 C 0.4216(5) 0.6825(4) 0.7841(2) 0.0617(9) Uani 1 1 d . . . C8 C 0.2672(5) 0.3898(4) 0.7302(3) 0.0834(12) Uani 1 1 d . . . H8A H 0.3173 0.3053 0.7199 0.100 Uiso 1 1 calc R . . H8B H 0.2188 0.4101 0.6659 0.100 Uiso 1 1 calc R . . C9 C 0.1109(7) 0.3334(6) 0.7762(5) 0.1236(18) Uani 1 1 d . . . H9A H 0.1590 0.3208 0.8420 0.185 Uiso 1 1 calc R . . H9B H 0.0218 0.2323 0.7375 0.185 Uiso 1 1 calc R . . H9C H 0.0503 0.4106 0.7792 0.185 Uiso 1 1 calc R . . C10 C 0.5757(6) 0.5177(5) 0.8596(4) 0.0992(14) Uani 1 1 d . . . H10A H 0.6262 0.6072 0.9156 0.119 Uiso 1 1 calc R . . H10B H 0.5308 0.4196 0.8838 0.119 Uiso 1 1 calc R . . C11 C 0.7182(8) 0.5133(7) 0.8134(5) 0.1361(19) Uani 1 1 d . . . H11A H 0.6667 0.4271 0.7564 0.204 Uiso 1 1 calc R . . H11B H 0.8169 0.4965 0.8591 0.204 Uiso 1 1 calc R . . H11C H 0.7679 0.6131 0.7932 0.204 Uiso 1 1 calc R . . C12 C 0.2771(5) 0.9352(4) 0.8058(3) 0.0647(9) Uani 1 1 d . . . C13 C 0.2179(7) 0.9353(6) 0.9640(3) 0.1040(14) Uani 1 1 d . . . H13A H 0.3452 1.0097 0.9947 0.125 Uiso 1 1 calc R . . H13B H 0.1356 0.9964 0.9556 0.125 Uiso 1 1 calc R . . C14 C 0.1621(9) 0.8241(7) 1.0258(4) 0.142(2) Uani 1 1 d . . . H14A H 0.0333 0.7553 0.9972 0.214 Uiso 1 1 calc R . . H14B H 0.1752 0.8817 1.0902 0.214 Uiso 1 1 calc R . . H14C H 0.2402 0.7606 1.0313 0.214 Uiso 1 1 calc R . . C15 C 0.4699(6) 0.7005(5) 0.5384(3) 0.0931(12) Uani 1 1 d . . . H15A H 0.4139 0.6103 0.4839 0.140 Uiso 1 1 calc R . . H15B H 0.5115 0.6653 0.5977 0.140 Uiso 1 1 calc R . . H15C H 0.5753 0.7783 0.5254 0.140 Uiso 1 1 calc R . . C16 C 0.5570(5) 1.0303(4) 0.6758(3) 0.0801(11) Uani 1 1 d . . . H16A H 0.6044 1.0693 0.6225 0.120 Uiso 1 1 calc R . . H16B H 0.6358 0.9797 0.7095 0.120 Uiso 1 1 calc R . . H16C H 0.5567 1.1183 0.7213 0.120 Uiso 1 1 calc R . . N1 N 0.4193(4) 0.5349(3) 0.7891(2) 0.0749(9) Uani 1 1 d . . . O1 O 0.2356(3) 0.9870(3) 0.59069(18) 0.0755(7) Uani 1 1 d . . . O2 O 0.2633(3) 0.6781(2) 0.71935(15) 0.0587(6) Uani 1 1 d . . . O3 O 0.5456(3) 0.8073(3) 0.82990(17) 0.0768(8) Uani 1 1 d . . . O4 O 0.3453(4) 1.0795(3) 0.82381(18) 0.0830(8) Uani 1 1 d . . . O5 O 0.2084(3) 0.8486(3) 0.86819(17) 0.0756(7) Uani 1 1 d . . . F1 F -0.0695(3) 0.6349(2) 0.62938(16) 0.0824(7) Uani 1 1 d . . . F2 F -0.0430(3) 0.8763(3) 0.68722(17) 0.0906(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0614(19) 0.0416(17) 0.064(2) 0.0141(15) 0.0102(15) 0.0250(15) C2 0.057(2) 0.048(2) 0.094(3) 0.0141(18) 0.0114(17) 0.0242(17) C3 0.065(2) 0.059(2) 0.081(3) 0.0178(18) -0.0070(18) 0.0236(19) C4 0.086(3) 0.069(2) 0.063(2) 0.0121(18) 0.0015(19) 0.027(2) C5 0.075(2) 0.069(2) 0.058(2) 0.0195(17) 0.0117(17) 0.0300(19) C6 0.068(2) 0.0494(19) 0.067(2) 0.0182(16) 0.0088(16) 0.0234(17) C7 0.063(2) 0.053(2) 0.065(2) 0.0103(17) 0.0052(17) 0.0235(18) C8 0.079(3) 0.052(2) 0.106(3) 0.013(2) -0.007(2) 0.028(2) C9 0.090(3) 0.092(3) 0.186(5) 0.049(3) 0.029(3) 0.027(3) C10 0.079(3) 0.071(3) 0.142(4) 0.026(3) 0.009(3) 0.033(2) C11 0.102(4) 0.132(5) 0.167(5) 0.035(4) 0.018(4) 0.041(3) C12 0.071(2) 0.055(2) 0.072(2) 0.0177(19) 0.0144(17) 0.0279(18) C13 0.129(4) 0.112(4) 0.075(3) 0.010(3) 0.037(3) 0.045(3) C14 0.160(5) 0.152(5) 0.084(3) 0.020(3) 0.043(3) 0.011(4) C15 0.093(3) 0.105(3) 0.089(3) 0.015(2) 0.023(2) 0.049(3) C16 0.067(2) 0.069(2) 0.089(3) 0.0195(19) 0.0136(19) 0.0087(19) N1 0.076(2) 0.0534(17) 0.089(2) 0.0201(15) -0.0069(16) 0.0316(15) O1 0.0801(16) 0.0563(14) 0.0906(17) 0.0297(12) 0.0066(13) 0.0300(13) O2 0.0633(14) 0.0450(12) 0.0646(14) 0.0122(9) 0.0025(10) 0.0240(10) O3 0.0736(15) 0.0585(15) 0.0812(17) 0.0068(12) -0.0075(12) 0.0216(13) O4 0.108(2) 0.0496(16) 0.0874(18) 0.0080(12) 0.0175(14) 0.0304(14) O5 0.0891(17) 0.0663(15) 0.0698(16) 0.0127(13) 0.0234(13) 0.0249(13) F1 0.0608(12) 0.0617(13) 0.1081(16) 0.0188(11) 0.0041(10) 0.0114(10) F2 0.0718(13) 0.0870(15) 0.1199(18) 0.0139(13) 0.0176(12) 0.0449(12) _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 C1 O2 1.433(3) . ? C1 C12 1.513(5) . ? C1 C2 1.567(5) . ? C1 C6 1.573(5) . ? C2 F2 1.351(4) . ? C2 F1 1.361(4) . ? C2 C3 1.512(5) . ? C3 O1 1.456(4) . ? C3 C4 1.482(5) . ? C4 C5 1.324(5) . ? C5 C15 1.487(5) . ? C5 C6 1.515(5) . ? C6 O1 1.443(4) . ? C6 C16 1.507(5) . ? C7 O3 1.214(4) . ? C7 N1 1.333(4) . ? C7 O2 1.359(4) . ? C8 N1 1.458(4) . ? C8 C9 1.476(6) . ? C10 C11 1.411(7) . ? C10 N1 1.467(5) . ? C12 O4 1.205(4) . ? C12 O5 1.327(4) . ? C13 C14 1.428(7) . ? C13 O5 1.453(5) . ? 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 O2 C1 C12 111.9(2) . . ? O2 C1 C2 106.0(2) . . ? C12 C1 C2 108.7(3) . . ? O2 C1 C6 113.2(2) . . ? C12 C1 C6 116.8(3) . . ? C2 C1 C6 98.7(2) . . ? F2 C2 F1 105.2(3) . . ? F2 C2 C3 111.2(3) . . ? F1 C2 C3 112.6(3) . . ? F2 C2 C1 111.0(3) . . ? F1 C2 C1 113.6(2) . . ? C3 C2 C1 103.4(3) . . ? O1 C3 C4 102.7(3) . . ? O1 C3 C2 97.4(3) . . ? C4 C3 C2 108.4(3) . . ? C5 C4 C3 107.1(3) . . ? C4 C5 C15 129.6(3) . . ? C4 C5 C6 105.4(3) . . ? C15 C5 C6 125.0(3) . . ? O1 C6 C16 110.4(3) . . ? O1 C6 C5 102.5(3) . . ? C16 C6 C5 116.8(3) . . ? O1 C6 C1 99.6(2) . . ? C16 C6 C1 119.6(3) . . ? C5 C6 C1 105.4(3) . . ? O3 C7 N1 126.3(3) . . ? O3 C7 O2 122.6(3) . . ? N1 C7 O2 111.1(3) . . ? N1 C8 C9 113.5(4) . . ? C11 C10 N1 110.2(4) . . ? O4 C12 O5 124.1(3) . . ? O4 C12 C1 124.5(3) . . ? O5 C12 C1 111.3(3) . . ? C14 C13 O5 109.5(4) . . ? C7 N1 C8 123.5(3) . . ? C7 N1 C10 118.2(3) . . ? C8 N1 C10 118.3(3) . . ? C6 O1 C3 96.5(2) . . ? C7 O2 C1 116.5(2) . . ? C12 O5 C13 117.2(3) . . ? _diffrn_measured_fraction_theta_max 0.897 _diffrn_reflns_theta_full 55.17 _diffrn_measured_fraction_theta_full 0.897 _refine_diff_density_max 0.448 _refine_diff_density_min -0.177 _refine_diff_density_rms 0.044 #===END data_16 _database_code_depnum_ccdc_archive 'CCDC 224034' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H10 F2 O6' _chemical_formula_weight 264.18 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' 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.3657(7) _cell_length_b 7.5078(7) _cell_length_c 10.1384(9) _cell_angle_alpha 77.063(2) _cell_angle_beta 78.383(2) _cell_angle_gamma 89.452(2) _cell_volume 534.86(9) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2369 _cell_measurement_theta_min 2.77 _cell_measurement_theta_max 27.85 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.640 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 272 _exptl_absorpt_coefficient_mu 0.157 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3895 _diffrn_reflns_av_R_equivalents 0.0309 _diffrn_reflns_av_sigmaI/netI 0.0315 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1866 _reflns_number_gt 1648 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0470P)^2^+0.0755P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1866 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0354 _refine_ls_R_factor_gt 0.0316 _refine_ls_wR_factor_ref 0.0871 _refine_ls_wR_factor_gt 0.0851 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.017 _refine_ls_shift/su_mean 0.002 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F1 F 0.09090(11) 0.17923(11) 0.98351(8) 0.0277(2) Uani 1 1 d . . . F2 F 0.26386(11) 0.02578(10) 0.85090(9) 0.0290(2) Uani 1 1 d . . . O1 O 0.11514(15) 0.56096(14) 0.59274(11) 0.0319(3) Uani 1 1 d . . . O2 O 0.30723(17) 0.48871(16) 0.41177(11) 0.0412(3) Uani 1 1 d . . . O3 O 0.24432(13) 0.29012(13) 0.61748(10) 0.0250(3) Uani 1 1 d . . . O4 O 0.45017(14) 0.23393(15) 0.98510(10) 0.0310(3) Uani 1 1 d . . . H4 H 0.5516 0.1852 0.9633 0.046 Uiso 1 1 calc R . . O5 O -0.20157(14) 0.18321(14) 0.83287(11) 0.0288(3) Uani 1 1 d . . . O6 O -0.03118(14) 0.04893(14) 0.67447(11) 0.0283(3) Uani 1 1 d . . . C2 C 0.2295(2) 0.4518(2) 0.52939(16) 0.0289(4) Uani 1 1 d . . . C3A C 0.11516(19) 0.28125(19) 0.74542(14) 0.0221(3) Uani 1 1 d . . . C4 C 0.21494(19) 0.19741(18) 0.86202(14) 0.0223(3) Uani 1 1 d . . . C5 C 0.3826(2) 0.3109(2) 0.86410(14) 0.0250(3) Uani 1 1 d . . . H5 H 0.4812 0.3087 0.7808 0.030 Uiso 1 1 calc R . . C6 C 0.3281(2) 0.5035(2) 0.86222(16) 0.0315(4) Uani 1 1 d . . . H6 H 0.3981 0.5758 0.9014 0.038 Uiso 1 1 calc R . . C7 C 0.1885(2) 0.5791(2) 0.80938(16) 0.0315(4) Uani 1 1 d . . . H7 H 0.1614 0.7015 0.8149 0.038 Uiso 1 1 calc R . . C7A C 0.0708(2) 0.48246(19) 0.74147(15) 0.0259(3) Uani 1 1 d . . . H7A H -0.0637 0.4943 0.7798 0.031 Uiso 1 1 calc R . . C8 C -0.0599(2) 0.16515(19) 0.75514(14) 0.0230(3) Uani 1 1 d . . . C9 C -0.1879(2) -0.0770(2) 0.68335(17) 0.0316(4) Uani 1 1 d . . . H9A H -0.2535 -0.1168 0.7810 0.038 Uiso 1 1 calc R . . H9B H -0.1399 -0.1869 0.6513 0.038 Uiso 1 1 calc R . . C10 C -0.3217(2) 0.0117(2) 0.59758(17) 0.0344(4) Uani 1 1 d . . . H10A H -0.3742 0.1169 0.6322 0.052 Uiso 1 1 calc R . . H10B H -0.4216 -0.0767 0.6033 0.052 Uiso 1 1 calc R . . H10C H -0.2567 0.0529 0.5011 0.052 Uiso 1 1 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_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.0239(5) 0.0348(5) 0.0215(4) -0.0018(4) -0.0026(3) -0.0027(4) F2 0.0311(5) 0.0218(5) 0.0350(5) -0.0049(4) -0.0106(4) 0.0036(4) O1 0.0403(6) 0.0250(6) 0.0289(6) 0.0005(4) -0.0108(5) 0.0009(5) O2 0.0479(7) 0.0450(7) 0.0241(6) 0.0020(5) -0.0024(5) -0.0101(6) O3 0.0256(6) 0.0260(5) 0.0208(5) -0.0028(4) -0.0015(4) -0.0014(4) O4 0.0239(6) 0.0423(6) 0.0275(6) -0.0058(5) -0.0094(5) 0.0019(5) O5 0.0224(6) 0.0342(6) 0.0281(6) -0.0050(5) -0.0034(5) -0.0002(4) O6 0.0251(6) 0.0288(6) 0.0337(6) -0.0113(5) -0.0073(5) -0.0022(4) C2 0.0306(8) 0.0290(8) 0.0255(8) -0.0009(6) -0.0079(7) -0.0066(7) C3A 0.0206(7) 0.0246(7) 0.0202(7) -0.0050(6) -0.0021(6) 0.0009(6) C4 0.0227(7) 0.0218(7) 0.0207(7) -0.0039(6) -0.0018(6) 0.0011(6) C5 0.0234(8) 0.0305(8) 0.0213(7) -0.0047(6) -0.0059(6) -0.0016(6) C6 0.0351(9) 0.0308(8) 0.0309(9) -0.0096(7) -0.0087(7) -0.0063(7) C7 0.0396(9) 0.0231(8) 0.0337(9) -0.0089(6) -0.0090(7) 0.0006(7) C7A 0.0277(8) 0.0233(8) 0.0256(8) -0.0027(6) -0.0062(6) 0.0008(6) C8 0.0248(8) 0.0218(7) 0.0220(7) -0.0005(6) -0.0082(6) 0.0016(6) C9 0.0315(9) 0.0275(8) 0.0381(9) -0.0077(7) -0.0118(7) -0.0059(7) C10 0.0293(9) 0.0399(9) 0.0381(9) -0.0135(7) -0.0111(7) 0.0006(7) _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 F1 C4 1.3581(16) . ? F2 C4 1.3575(16) . ? O1 C2 1.3413(19) . ? O1 C7A 1.4613(18) . ? O2 C2 1.1860(18) . ? O3 C2 1.3541(18) . ? O3 C3A 1.4344(16) . ? O4 C5 1.4175(17) . ? O5 C8 1.2007(17) . ? O6 C8 1.3120(17) . ? O6 C9 1.4750(17) . ? C3A C4 1.5302(19) . ? C3A C7A 1.536(2) . ? C3A C8 1.538(2) . ? C4 C5 1.5132(19) . ? C5 C6 1.494(2) . ? C6 C7 1.319(2) . ? C7 C7A 1.492(2) . ? C9 C10 1.498(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 C2 O1 C7A 109.57(11) . . ? C2 O3 C3A 109.18(11) . . ? C8 O6 C9 116.51(12) . . ? O2 C2 O1 125.38(14) . . ? O2 C2 O3 123.63(15) . . ? O1 C2 O3 110.99(12) . . ? O3 C3A C4 107.13(11) . . ? O3 C3A C7A 103.29(11) . . ? C4 C3A C7A 112.62(11) . . ? O3 C3A C8 111.58(11) . . ? C4 C3A C8 110.34(11) . . ? C7A C3A C8 111.62(12) . . ? F2 C4 F1 106.49(10) . . ? F2 C4 C5 110.56(11) . . ? F1 C4 C5 109.64(11) . . ? F2 C4 C3A 108.98(11) . . ? F1 C4 C3A 107.65(11) . . ? C5 C4 C3A 113.26(11) . . ? O4 C5 C6 110.76(12) . . ? O4 C5 C4 108.60(11) . . ? C6 C5 C4 109.26(12) . . ? C7 C6 C5 123.87(14) . . ? C6 C7 C7A 123.50(14) . . ? O1 C7A C7 108.52(12) . . ? O1 C7A C3A 101.00(11) . . ? C7 C7A C3A 115.01(13) . . ? O5 C8 O6 127.00(13) . . ? O5 C8 C3A 120.45(13) . . ? O6 C8 C3A 112.52(12) . . ? O6 C9 C10 111.59(12) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.281 _refine_diff_density_min -0.168 _refine_diff_density_rms 0.041 #===END data_22a _database_code_depnum_ccdc_archive 'CCDC 224035' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H14 F2 O3' _chemical_formula_sum 'C11 H14 F2 O3' _chemical_formula_weight 232.22 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' F F 0.0171 0.0103 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M Cc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 9.7681(13) _cell_length_b 11.8090(15) _cell_length_c 10.5162(15) _cell_angle_alpha 90.00 _cell_angle_beta 114.677(9) _cell_angle_gamma 90.00 _cell_volume 1102.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 2308 _cell_measurement_theta_min 5.42 _cell_measurement_theta_max 28.7 _exptl_crystal_description Block _exptl_crystal_colour Clear _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.399 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.122 _exptl_absorpt_correction_type None _exptl_absorpt_correction_T_min 0.9529 _exptl_absorpt_correction_T_max 0.9529 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku R-axis IIc image plate' _diffrn_measurement_method 'Image plate slices' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4540 _diffrn_reflns_av_R_equivalents 0.0503 _diffrn_reflns_av_sigmaI/netI 0.0344 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 5.42 _diffrn_reflns_theta_max 28.70 _reflns_number_total 2373 _reflns_number_gt 2308 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'MSC software' _computing_cell_refinement 'MSC software' _computing_data_reduction 'MSC software' _computing_structure_solution SHELXS86 _computing_structure_refinement SHELXL97 _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1330P)^2^+1.0035P] 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 -1.4(11) _refine_ls_number_reflns 2373 _refine_ls_number_parameters 148 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0604 _refine_ls_R_factor_gt 0.0563 _refine_ls_wR_factor_ref 0.2013 _refine_ls_wR_factor_gt 0.1948 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.082 _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 F1 F 0.7240(3) 0.18096(17) 0.6339(2) 0.0439(5) Uani 1 1 d . . . F2 F 0.6669(3) 0.27130(15) 0.7839(2) 0.0449(5) Uani 1 1 d . . . O1 O 0.4737(3) 0.03675(17) 0.5894(2) 0.0345(5) Uani 1 1 d . . . O2 O 0.9022(3) 0.09020(18) 0.9971(2) 0.0385(5) Uani 1 1 d . . . O3 O 0.7965(3) 0.00138(19) 0.7864(2) 0.0336(5) Uani 1 1 d . . . C1 C 0.6798(3) 0.0637(2) 0.8021(3) 0.0285(5) Uani 1 1 d . . . C2 C 0.6395(4) 0.1732(2) 0.7088(3) 0.0334(6) Uani 1 1 d . . . C3 C 0.4713(4) 0.1558(2) 0.6120(3) 0.0364(6) Uani 1 1 d . . . H3 H 0.4311 0.2034 0.5255 0.044 Uiso 1 1 calc R . . C4 C 0.3855(4) 0.1637(3) 0.7034(4) 0.0397(7) Uani 1 1 d . . . H4 H 0.3220 0.2236 0.7063 0.048 Uiso 1 1 calc R . . C5 C 0.4179(4) 0.0695(3) 0.7782(3) 0.0390(7) Uani 1 1 d . . . H5 H 0.3820 0.0479 0.8458 0.047 Uiso 1 1 calc R . . C6 C 0.5252(3) 0.0019(2) 0.7340(3) 0.0315(6) Uani 1 1 d . . . C7 C 0.7441(4) 0.0839(3) 0.9592(3) 0.0348(6) Uani 1 1 d . . . H7A H 0.7056 0.1555 0.9811 0.042 Uiso 1 1 calc R . . H7B H 0.7195 0.0206 1.0077 0.042 Uiso 1 1 calc R . . C8 C 0.9346(3) 0.0094(2) 0.9126(3) 0.0323(6) Uani 1 1 d . . . C9 C 1.0598(5) 0.0544(3) 0.8789(5) 0.0498(8) Uani 1 1 d . . . H9A H 1.0826 -0.0005 0.8205 0.075 Uiso 1 1 calc R . . H9B H 1.1498 0.0668 0.9659 0.075 Uiso 1 1 calc R . . H9C H 1.0284 0.1262 0.8282 0.075 Uiso 1 1 calc R . . C10 C 0.9693(5) -0.1055(3) 0.9838(4) 0.0445(7) Uani 1 1 d . . . H10A H 0.9790 -0.1618 0.9196 0.067 Uiso 1 1 calc R . . H10B H 0.8873 -0.1276 1.0093 0.067 Uiso 1 1 calc R . . H10C H 1.0638 -0.1012 1.0683 0.067 Uiso 1 1 calc R . . C11 C 0.5279(5) -0.1244(3) 0.7478(4) 0.0458(8) Uani 1 1 d . . . H11A H 0.4245 -0.1534 0.7076 0.069 Uiso 1 1 calc R . . H11B H 0.5774 -0.1451 0.8470 0.069 Uiso 1 1 calc R . . H11C H 0.5836 -0.1572 0.6979 0.069 Uiso 1 1 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_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.0498(12) 0.0433(10) 0.0446(11) 0.0070(8) 0.0256(10) -0.0004(8) F2 0.0532(12) 0.0258(8) 0.0462(11) -0.0057(7) 0.0113(10) -0.0012(7) O1 0.0382(11) 0.0347(10) 0.0227(9) -0.0022(7) 0.0049(8) -0.0021(8) O2 0.0317(11) 0.0405(11) 0.0322(10) -0.0123(8) 0.0025(9) 0.0007(8) O3 0.0327(11) 0.0363(9) 0.0250(9) -0.0062(7) 0.0053(8) 0.0046(7) C1 0.0329(14) 0.0264(10) 0.0225(11) -0.0028(8) 0.0079(10) -0.0005(9) C2 0.0418(16) 0.0282(11) 0.0285(13) -0.0016(9) 0.0128(12) 0.0000(10) C3 0.0428(16) 0.0330(13) 0.0272(14) 0.0042(9) 0.0085(12) 0.0053(11) C4 0.0335(16) 0.0479(16) 0.0323(14) -0.0003(11) 0.0083(12) 0.0071(12) C5 0.0320(15) 0.0518(17) 0.0308(14) 0.0017(12) 0.0108(12) 0.0002(11) C6 0.0312(14) 0.0337(12) 0.0235(12) 0.0017(9) 0.0053(10) -0.0026(10) C7 0.0354(15) 0.0402(13) 0.0221(12) -0.0055(9) 0.0054(11) -0.0002(10) C8 0.0275(13) 0.0349(12) 0.0288(13) -0.0030(10) 0.0062(11) 0.0020(10) C9 0.0392(18) 0.054(2) 0.056(2) -0.0003(16) 0.0194(17) -0.0020(14) C10 0.049(2) 0.0414(16) 0.0364(16) 0.0036(12) 0.0108(14) 0.0095(13) C11 0.049(2) 0.0344(14) 0.0484(18) 0.0018(12) 0.0148(16) -0.0113(12) _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 F1 C2 1.362(4) . ? F2 C2 1.364(3) . ? O1 C3 1.427(4) . ? O1 C6 1.448(3) . ? O2 C8 1.426(3) . ? O2 C7 1.427(4) . ? O3 C1 1.423(3) . ? O3 C8 1.447(4) . ? C1 C7 1.521(4) . ? C1 C6 1.557(4) . ? C1 C2 1.571(4) . ? C2 C3 1.543(5) . ? C3 C4 1.519(5) . ? C4 C5 1.322(5) . ? C5 C6 1.536(5) . ? C6 C11 1.497(4) . ? C8 C9 1.505(5) . ? C8 C10 1.517(4) . ? 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 C3 O1 C6 97.4(2) . . ? C8 O2 C7 106.7(2) . . ? C1 O3 C8 110.2(2) . . ? O3 C1 C7 102.7(2) . . ? O3 C1 C6 112.0(2) . . ? C7 C1 C6 117.0(2) . . ? O3 C1 C2 111.0(2) . . ? C7 C1 C2 115.5(2) . . ? C6 C1 C2 99.0(2) . . ? F1 C2 F2 105.0(2) . . ? F1 C2 C3 111.3(3) . . ? F2 C2 C3 113.1(3) . . ? F1 C2 C1 111.2(2) . . ? F2 C2 C1 113.6(2) . . ? C3 C2 C1 102.9(2) . . ? O1 C3 C4 102.6(2) . . ? O1 C3 C2 98.9(2) . . ? C4 C3 C2 106.9(2) . . ? C5 C4 C3 105.5(3) . . ? C4 C5 C6 106.4(3) . . ? O1 C6 C11 111.7(3) . . ? O1 C6 C5 100.9(2) . . ? C11 C6 C5 118.4(3) . . ? O1 C6 C1 101.2(2) . . ? C11 C6 C1 116.6(3) . . ? C5 C6 C1 105.7(2) . . ? O2 C7 C1 102.7(2) . . ? O2 C8 O3 104.5(2) . . ? O2 C8 C9 108.9(3) . . ? O3 C8 C9 110.2(3) . . ? O2 C8 C10 110.7(3) . . ? O3 C8 C10 108.9(2) . . ? C9 C8 C10 113.3(3) . . ? _diffrn_measured_fraction_theta_max 0.934 _diffrn_reflns_theta_full 28.70 _diffrn_measured_fraction_theta_full 0.934 _refine_diff_density_max 0.230 _refine_diff_density_min -0.298 _refine_diff_density_rms 0.060 #===END data_31 _database_code_depnum_ccdc_archive 'CCDC 224036' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H16 F2 O3' _chemical_formula_sum 'C11 H16 F2 O3' _chemical_formula_weight 234.24 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' 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/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.8294(12) _cell_length_b 8.3435(13) _cell_length_c 13.9113(16) _cell_angle_alpha 90.00 _cell_angle_beta 98.998(10) _cell_angle_gamma 90.00 _cell_volume 1126.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 1818 _cell_measurement_theta_min 2.75 _cell_measurement_theta_max 28.7 _exptl_crystal_description block _exptl_crystal_colour clear _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.381 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.120 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9537 _exptl_absorpt_correction_T_max 0.9650 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku R-axis IIc Image plate' _diffrn_measurement_method 'Image plate slices' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8756 _diffrn_reflns_av_R_equivalents 0.0792 _diffrn_reflns_av_sigmaI/netI 0.0798 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.75 _diffrn_reflns_theta_max 28.70 _reflns_number_total 2615 _reflns_number_gt 1818 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'MSC Software' _computing_cell_refinement 'MSC Software' _computing_data_reduction 'MSC Software' _computing_structure_solution SHELXS86 _computing_structure_refinement SHELXL97 _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1341P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2615 _refine_ls_number_parameters 152 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0860 _refine_ls_R_factor_gt 0.0646 _refine_ls_wR_factor_ref 0.2216 _refine_ls_wR_factor_gt 0.1743 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.011 _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 O1 O 0.68104(16) 0.34485(18) 0.50665(11) 0.0299(4) Uani 1 1 d . . . O2 O 0.88700(17) 0.43949(19) 0.58690(11) 0.0352(4) Uani 1 1 d . . . O3 O 0.8272(2) 0.4511(2) 0.36262(12) 0.0369(4) Uani 1 1 d . . . F1 F 0.70824(17) 0.04677(18) 0.57809(10) 0.0436(4) Uani 1 1 d . . . F2 F 0.85039(16) -0.02924(16) 0.48284(11) 0.0438(4) Uani 1 1 d . . . C1 C 0.7858(2) 0.2454(2) 0.47679(14) 0.0282(5) Uani 1 1 d . . . C2 C 0.7390(3) 0.0718(3) 0.48627(16) 0.0328(5) Uani 1 1 d . . . C3 C 0.6205(2) 0.0231(3) 0.41178(17) 0.0350(5) Uani 1 1 d . . . H3 H 0.5720 -0.0727 0.4210 0.042 Uiso 1 1 calc R . . C4 C 0.5812(2) 0.1109(3) 0.33270(16) 0.0361(5) Uani 1 1 d . . . H4 H 0.5043 0.0748 0.2879 0.043 Uiso 1 1 calc R . . C5 C 0.6500(2) 0.2632(3) 0.30942(16) 0.0354(5) Uani 1 1 d . . . H5A H 0.5916 0.3551 0.3220 0.043 Uiso 1 1 calc R . . H5B H 0.6575 0.2639 0.2393 0.043 Uiso 1 1 calc R . . C6 C 0.7951(2) 0.2854(3) 0.36915(15) 0.0304(5) Uani 1 1 d . . . C7 C 0.9012(3) 0.1839(3) 0.32598(17) 0.0410(6) Uani 1 1 d . . . H7A H 0.8696 0.0724 0.3196 0.062 Uiso 1 1 calc R . . H7B H 0.9901 0.1887 0.3690 0.062 Uiso 1 1 calc R . . H7C H 0.9115 0.2258 0.2617 0.062 Uiso 1 1 calc R . . C8 C 0.9159(2) 0.2858(3) 0.55032(15) 0.0316(5) Uani 1 1 d . . . H8A H 0.9310 0.2056 0.6033 0.038 Uiso 1 1 calc R . . H8B H 0.9985 0.2897 0.5178 0.038 Uiso 1 1 calc R . . C9 C 0.7394(2) 0.4530(3) 0.58263(15) 0.0318(5) Uani 1 1 d . . . C10 C 0.6972(3) 0.6220(3) 0.5531(2) 0.0437(6) Uani 1 1 d . . . H10A H 0.5970 0.6322 0.5474 0.066 Uiso 1 1 calc R . . H10B H 0.7257 0.6465 0.4902 0.066 Uiso 1 1 calc R . . H10C H 0.7417 0.6971 0.6024 0.066 Uiso 1 1 calc R . . C11 C 0.6956(3) 0.4018(4) 0.67754(18) 0.0480(7) Uani 1 1 d . . . H11A H 0.5949 0.3945 0.6691 0.072 Uiso 1 1 calc R . . H11B H 0.7278 0.4808 0.7281 0.072 Uiso 1 1 calc R . . H11C H 0.7358 0.2969 0.6968 0.072 Uiso 1 1 calc R . . H12 H 0.909(3) 0.464(4) 0.373(2) 0.042(8) 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 O1 0.0353(9) 0.0289(8) 0.0245(7) -0.0046(6) 0.0015(6) 0.0002(6) O2 0.0350(9) 0.0326(9) 0.0359(9) -0.0099(6) -0.0007(6) -0.0006(6) O3 0.0467(12) 0.0304(9) 0.0334(9) 0.0054(6) 0.0054(7) -0.0047(7) F1 0.0597(10) 0.0405(8) 0.0297(7) 0.0092(6) 0.0044(6) -0.0087(7) F2 0.0448(9) 0.0265(7) 0.0579(9) 0.0033(6) 0.0017(7) 0.0062(6) C1 0.0357(11) 0.0251(10) 0.0226(9) -0.0003(7) 0.0009(7) 0.0011(8) C2 0.0431(13) 0.0262(10) 0.0278(10) 0.0027(8) 0.0010(9) 0.0031(9) C3 0.0365(13) 0.0305(11) 0.0374(12) -0.0070(9) 0.0042(9) -0.0061(9) C4 0.0324(12) 0.0430(13) 0.0313(11) -0.0090(9) 0.0002(8) -0.0032(9) C5 0.0428(13) 0.0395(13) 0.0220(10) -0.0001(8) -0.0013(8) 0.0019(9) C6 0.0401(12) 0.0272(10) 0.0233(10) 0.0003(7) 0.0024(8) 0.0004(8) C7 0.0539(15) 0.0390(13) 0.0312(12) -0.0051(9) 0.0099(10) -0.0013(11) C8 0.0383(12) 0.0278(11) 0.0269(10) -0.0034(8) -0.0009(8) 0.0005(8) C9 0.0367(12) 0.0305(11) 0.0275(10) -0.0067(8) 0.0026(8) -0.0054(8) C10 0.0467(15) 0.0331(13) 0.0513(15) -0.0083(11) 0.0074(11) 0.0027(10) C11 0.0625(18) 0.0538(17) 0.0282(12) -0.0066(10) 0.0090(11) -0.0059(13) _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 O1 C1 1.433(3) . ? O1 C9 1.439(2) . ? O2 C8 1.425(3) . ? O2 C9 1.447(3) . ? O3 C6 1.424(3) . ? F1 C2 1.374(3) . ? F2 C2 1.389(3) . ? C1 C2 1.532(3) . ? C1 C8 1.545(3) . ? C1 C6 1.551(3) . ? C2 C3 1.489(3) . ? C3 C4 1.328(3) . ? C4 C5 1.498(3) . ? C5 C6 1.545(3) . ? C6 C7 1.536(3) . ? C9 C10 1.509(3) . ? C9 C11 1.513(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 C1 O1 C9 110.72(16) . . ? C8 O2 C9 108.07(16) . . ? O1 C1 C2 106.48(18) . . ? O1 C1 C8 103.88(16) . . ? C2 C1 C8 112.19(17) . . ? O1 C1 C6 108.01(16) . . ? C2 C1 C6 110.50(17) . . ? C8 C1 C6 115.12(18) . . ? F1 C2 F2 103.25(17) . . ? F1 C2 C3 110.1(2) . . ? F2 C2 C3 110.22(18) . . ? F1 C2 C1 109.66(17) . . ? F2 C2 C1 108.80(19) . . ? C3 C2 C1 114.23(18) . . ? C4 C3 C2 121.4(2) . . ? C3 C4 C5 124.3(2) . . ? C4 C5 C6 113.27(19) . . ? O3 C6 C7 109.84(19) . . ? O3 C6 C5 106.08(18) . . ? C7 C6 C5 110.46(18) . . ? O3 C6 C1 108.49(17) . . ? C7 C6 C1 113.92(18) . . ? C5 C6 C1 107.73(18) . . ? O2 C8 C1 103.99(17) . . ? O1 C9 O2 105.28(17) . . ? O1 C9 C10 108.95(18) . . ? O2 C9 C10 108.35(19) . . ? O1 C9 C11 109.21(19) . . ? O2 C9 C11 111.3(2) . . ? C10 C9 C11 113.5(2) . . ? _diffrn_measured_fraction_theta_max 0.900 _diffrn_reflns_theta_full 28.70 _diffrn_measured_fraction_theta_full 0.900 _refine_diff_density_max 0.355 _refine_diff_density_min -0.432 _refine_diff_density_rms 0.076 #===END