data_bashir4m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H5 F3 N2 O' _chemical_formula_sum 'C8 H5 F3 N2 O' _chemical_formula_weight 202.14 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 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 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.0768(6) _cell_length_b 7.6010(7) _cell_length_c 8.4460(8) _cell_angle_alpha 105.0130(10) _cell_angle_beta 93.805(2) _cell_angle_gamma 106.5840(10) _cell_volume 415.70(7) _cell_formula_units_Z 2 _cell_measurement_temperature 295(1) _cell_measurement_reflns_used 2074 _cell_measurement_theta_min 2.53 _cell_measurement_theta_max 27.91 _exptl_crystal_description shapeless _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.615 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 204 _exptl_absorpt_coefficient_mu 0.155 _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 295(1) _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 4418 _diffrn_reflns_av_R_equivalents 0.0156 _diffrn_reflns_av_sigmaI/netI 0.0190 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.53 _diffrn_reflns_theta_max 26.98 _reflns_number_total 1787 _reflns_number_gt 1600 _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^)+(0.0788P)^2^+0.2171P] 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 0.026(11) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1787 _refine_ls_number_parameters 148 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0632 _refine_ls_R_factor_gt 0.0584 _refine_ls_wR_factor_ref 0.1604 _refine_ls_wR_factor_gt 0.1564 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _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 C1 C 0.3421(3) 0.1519(3) 0.8015(3) 0.0451(5) Uani 1 1 d . . . C2 C 0.5412(3) 0.2473(3) 0.8198(3) 0.0468(5) Uani 1 1 d . . . C3 C 0.6230(3) 0.2923(3) 0.6842(2) 0.0402(5) Uani 1 1 d . . . C4 C 0.5053(3) 0.2434(3) 0.5325(2) 0.0374(4) Uani 1 1 d . . . C5 C 0.2956(3) 0.1389(3) 0.5109(2) 0.0387(5) Uani 1 1 d . . . C6 C 0.5767(3) 0.2913(3) 0.3893(3) 0.0456(5) Uani 1 1 d . . . C7 C 0.8434(3) 0.3996(3) 0.7064(3) 0.0498(6) Uani 1 1 d . . . C8 C 0.2370(4) 0.0922(6) 0.9357(3) 0.0665(8) Uani 1 1 d . . . H8A H 0.328(7) 0.145(6) 1.041(6) 0.119(14) Uiso 1 1 d . . . H8B H 0.124(7) 0.118(6) 0.934(5) 0.113(14) Uiso 1 1 d . . . H8C H 0.193(7) -0.048(8) 0.909(6) 0.126(16) Uiso 1 1 d . . . F1 F 0.92966(18) 0.3339(2) 0.58038(17) 0.0610(5) Uani 1 1 d . . . F2 F 0.9428(2) 0.3829(3) 0.8378(2) 0.0905(7) Uani 1 1 d . . . F3 F 0.8731(3) 0.5816(2) 0.7214(3) 0.1008(8) Uani 1 1 d . . . H2 H 0.623(4) 0.282(3) 0.919(3) 0.048(6) Uiso 1 1 d . . . H1N1 H 0.103(4) 0.043(4) 0.644(3) 0.046(6) Uiso 1 1 d . . . N1 N 0.2289(2) 0.1023(3) 0.6519(2) 0.0421(4) Uani 1 1 d . . . N2 N 0.6282(3) 0.3302(4) 0.2743(3) 0.0667(7) Uani 1 1 d . . . O1 O 0.1807(2) 0.0830(2) 0.37867(17) 0.0490(4) 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 0.0376(10) 0.0601(13) 0.0380(10) 0.0170(9) 0.0084(8) 0.0132(9) C2 0.0381(10) 0.0621(13) 0.0362(10) 0.0152(9) 0.0015(8) 0.0096(9) C3 0.0324(10) 0.0441(11) 0.0410(10) 0.0108(8) 0.0054(8) 0.0089(8) C4 0.0326(9) 0.0410(10) 0.0381(10) 0.0120(8) 0.0070(7) 0.0099(8) C5 0.0322(9) 0.0462(11) 0.0394(10) 0.0149(8) 0.0062(7) 0.0126(8) C6 0.0334(10) 0.0558(12) 0.0427(11) 0.0148(9) 0.0033(8) 0.0068(9) C7 0.0373(11) 0.0558(13) 0.0453(11) 0.0099(9) 0.0025(9) 0.0029(9) C8 0.0481(14) 0.104(2) 0.0463(13) 0.0328(14) 0.0134(11) 0.0104(14) F1 0.0347(7) 0.0811(10) 0.0602(8) 0.0160(7) 0.0114(6) 0.0106(6) F2 0.0407(8) 0.1520(18) 0.0572(9) 0.0350(10) -0.0090(7) -0.0032(9) F3 0.0618(10) 0.0482(9) 0.172(2) 0.0118(10) 0.0315(12) 0.0006(7) N1 0.0264(8) 0.0570(11) 0.0414(9) 0.0173(8) 0.0065(7) 0.0081(7) N2 0.0501(12) 0.0973(18) 0.0491(12) 0.0330(12) 0.0097(9) 0.0065(11) O1 0.0324(7) 0.0704(10) 0.0402(8) 0.0201(7) 0.0023(6) 0.0074(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 C1 N1 1.351(3) . ? C1 C2 1.366(3) . ? C1 C8 1.493(3) . ? C2 C3 1.394(3) . ? C2 H2 0.92(3) . ? C3 C4 1.382(3) . ? C3 C7 1.512(3) . ? C4 C6 1.434(3) . ? C4 C5 1.443(3) . ? C5 O1 1.235(2) . ? C5 N1 1.375(2) . ? C6 N2 1.139(3) . ? C7 F3 1.309(3) . ? C7 F1 1.319(3) . ? C7 F2 1.328(3) . ? C8 H8A 0.98(5) . ? C8 H8B 0.88(5) . ? C8 H8C 0.98(5) . ? N1 H1N1 0.87(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 N1 C1 C2 119.24(19) . . ? N1 C1 C8 116.2(2) . . ? C2 C1 C8 124.6(2) . . ? C1 C2 C3 119.30(19) . . ? C1 C2 H2 121.6(16) . . ? C3 C2 H2 119.1(16) . . ? C4 C3 C2 120.92(18) . . ? C4 C3 C7 120.24(18) . . ? C2 C3 C7 118.83(18) . . ? C3 C4 C6 124.21(17) . . ? C3 C4 C5 120.19(18) . . ? C6 C4 C5 115.60(17) . . ? O1 C5 N1 120.83(17) . . ? O1 C5 C4 124.69(18) . . ? N1 C5 C4 114.48(17) . . ? N2 C6 C4 178.0(2) . . ? F3 C7 F1 106.8(2) . . ? F3 C7 F2 109.2(2) . . ? F1 C7 F2 105.0(2) . . ? F3 C7 C3 110.9(2) . . ? F1 C7 C3 112.92(17) . . ? F2 C7 C3 111.72(19) . . ? C1 C8 H8A 110(3) . . ? C1 C8 H8B 109(3) . . ? H8A C8 H8B 117(4) . . ? C1 C8 H8C 109(3) . . ? H8A C8 H8C 108(4) . . ? H8B C8 H8C 103(4) . . ? C1 N1 C5 125.84(17) . . ? C1 N1 H1N1 117.3(16) . . ? C5 N1 H1N1 116.9(16) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N1 O1 0.87(3) 1.93(3) 2.800(2) 178(2) 2_556 _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 26.98 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.441 _refine_diff_density_min -0.285 _refine_diff_density_rms 0.062