#============================================================================== data_global loop_ _journal_name_full 'European Journal of Chemistry' _journal_coden_ASTM EJCUA9 _journal_volume 12 _journal_issue 3 _journal_year 2021 _journal_page_first 304 _journal_page_last 313 #============================================================================== data_p _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H7 F O3' _chemical_formula_sum 'C8 H7 F O3' _chemical_formula_weight 170.14 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 'International Tables 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' 0.0492 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 'Monoclinic' _symmetry_space_group_name_H-M 'P 21/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 13.3087(17) _cell_length_b 4.9912(6) _cell_length_c 11.6018(15) _cell_angle_alpha 90.00 _cell_angle_beta 104.171(4) _cell_angle_gamma 90.00 _cell_volume 747.21(16) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8759 _cell_measurement_theta_min 6.9 _cell_measurement_theta_max 65.3 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.512 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 352 _exptl_absorpt_coefficient_mu 1.142 _exptl_absorpt_correction_type 'Multi-scan' _exptl_absorpt_correction_T_min 0.778 _exptl_absorpt_correction_T_max 0.796 _exptl_absorpt_process_details 'CrystalClear' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Rigaku XtaLAB mini' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8759 _diffrn_reflns_av_R_equivalents 0.0528 _diffrn_reflns_av_sigmaI/netI 0.0385 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 6.86 _diffrn_reflns_theta_max 65.31 _reflns_number_total 1246 _reflns_number_gt 1194 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Mercury' _computing_publication_material 'PLATON' _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^)+(0.0742P)^2^+0.1629P] 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 1246 _refine_ls_number_parameters 110 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0472 _refine_ls_R_factor_gt 0.0458 _refine_ls_wR_factor_ref 0.1313 _refine_ls_wR_factor_gt 0.1295 _refine_ls_goodness_of_fit_ref 1.108 _refine_ls_restrained_S_all 1.108 _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 0.55200(10) 0.8651(3) 0.17362(12) 0.0790(4) Uani 1 1 d . . . C2 C 0.61570(14) 0.6838(4) 0.13956(18) 0.0560(5) Uani 1 1 d . . . C3 C 0.61167(13) 0.6575(4) 0.02071(17) 0.0559(5) Uani 1 1 d . . . H3 H 0.5670 0.7625 -0.0356 0.067 Uiso 1 1 calc R . . C4 C 0.67587(12) 0.4708(3) -0.01321(14) 0.0507(4) Uani 1 1 d . . . H4 H 0.6738 0.4478 -0.0933 0.061 Uiso 1 1 calc R . . C5 C 0.74319(12) 0.3183(3) 0.07151(14) 0.0444(4) Uani 1 1 d . . . C6 C 0.74677(14) 0.3522(3) 0.19101(15) 0.0521(5) Uani 1 1 d . . . H6 H 0.7927 0.2517 0.2481 0.062 Uiso 1 1 calc R . . C7 C 0.68164(14) 0.5368(4) 0.22521(16) 0.0571(5) Uani 1 1 d . . . H7 H 0.6828 0.5601 0.3051 0.069 Uiso 1 1 calc R . . O8 O 0.80437(9) 0.1409(2) 0.02813(10) 0.0513(4) Uani 1 1 d . . . C9 C 0.86816(12) -0.0269(3) 0.11340(14) 0.0461(4) Uani 1 1 d . . . H9A H 0.8260 -0.1194 0.1582 0.055 Uiso 1 1 calc R . . H9B H 0.9185 0.0816 0.1685 0.055 Uiso 1 1 calc R . . C10 C 0.92377(11) -0.2283(3) 0.05632(14) 0.0446(4) Uani 1 1 d . . . O11 O 0.98233(9) -0.3851(2) 0.12769(10) 0.0578(4) Uani 1 1 d . . . O12 O 0.91065(9) -0.2343(2) -0.05459(10) 0.0553(4) Uani 1 1 d . . . H12 H 0.9490 -0.3474 -0.0722 0.083 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 0.0784(8) 0.0715(8) 0.0933(9) -0.0066(6) 0.0331(7) 0.0242(6) C2 0.0542(9) 0.0461(9) 0.0712(11) -0.0039(8) 0.0223(8) 0.0044(7) C3 0.0518(9) 0.0499(10) 0.0634(11) 0.0059(8) 0.0092(8) 0.0064(7) C4 0.0561(9) 0.0489(9) 0.0463(9) 0.0020(7) 0.0112(7) 0.0014(7) C5 0.0507(8) 0.0366(8) 0.0469(9) -0.0005(6) 0.0138(7) -0.0003(6) C6 0.0636(10) 0.0463(9) 0.0468(9) 0.0039(7) 0.0144(7) 0.0069(7) C7 0.0715(11) 0.0505(10) 0.0539(10) -0.0038(8) 0.0240(8) 0.0022(8) O8 0.0642(7) 0.0476(7) 0.0414(6) 0.0016(4) 0.0117(5) 0.0133(5) C9 0.0523(9) 0.0432(9) 0.0413(8) 0.0019(6) 0.0085(6) 0.0029(6) C10 0.0457(8) 0.0425(9) 0.0447(9) -0.0006(6) 0.0092(6) -0.0011(6) O11 0.0661(8) 0.0572(8) 0.0466(7) 0.0038(5) 0.0072(5) 0.0171(6) O12 0.0664(8) 0.0557(8) 0.0430(7) 0.0008(5) 0.0117(5) 0.0134(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 F1 C2 1.363(2) . ? C2 C7 1.367(3) . ? C2 C3 1.373(3) . ? C3 C4 1.385(2) . ? C3 H3 0.9300 . ? C4 C5 1.385(2) . ? C4 H4 0.9300 . ? C5 O8 1.3787(19) . ? C5 C6 1.386(2) . ? C6 C7 1.388(2) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? O8 C9 1.4104(19) . ? C9 C10 1.496(2) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 O12 1.256(2) . ? C10 O11 1.2606(19) . ? O12 H12 0.8200 . ? 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 F1 C2 C7 118.67(17) . . ? F1 C2 C3 118.71(16) . . ? C7 C2 C3 122.62(16) . . ? C2 C3 C4 118.32(16) . . ? C2 C3 H3 120.8 . . ? C4 C3 H3 120.8 . . ? C5 C4 C3 120.35(15) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? O8 C5 C4 115.55(14) . . ? O8 C5 C6 124.40(14) . . ? C4 C5 C6 120.04(15) . . ? C5 C6 C7 119.76(16) . . ? C5 C6 H6 120.1 . . ? C7 C6 H6 120.1 . . ? C2 C7 C6 118.89(16) . . ? C2 C7 H7 120.6 . . ? C6 C7 H7 120.6 . . ? C5 O8 C9 115.66(12) . . ? O8 C9 C10 111.51(12) . . ? O8 C9 H9A 109.3 . . ? C10 C9 H9A 109.3 . . ? O8 C9 H9B 109.3 . . ? C10 C9 H9B 109.3 . . ? H9A C9 H9B 108.0 . . ? O12 C10 O11 124.52(15) . . ? O12 C10 C9 120.66(14) . . ? O11 C10 C9 114.82(13) . . ? C10 O12 H12 109.5 . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 65.31 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.297 _refine_diff_density_min -0.266 _refine_diff_density_rms 0.075