# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Angelo Gavezzotti' _publ_contact_author_email ANGELO.GAVEZZOTTI@UNIMI.IT _publ_section_title ; Competition between hydrogen bonding and arene-perfluoroarene stacking. X-ray diffraction and molecular simulation on 5,6,7,8-tetrafluoro-2-naphthoic acid and 5,6,7,8-tetrafluoro-2-naphthamide crystals ; loop_ _publ_author_name 'Angelo Gavezzotti' 'Sergio Bacchi' 'Franco Cozzi' 'Giuseppe Filippini' 'Tullio Pilati' # Attachment 'msgave_cif.doc' data_cz7_93k _database_code_depnum_ccdc_archive 'CCDC 697372' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H4 F4 O2' _chemical_formula_sum 'C11 H4 F4 O2' _chemical_formula_weight 244.14 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' 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 4.943(2) _cell_length_b 5.902(2) _cell_length_c 30.706(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.880(10) _cell_angle_gamma 90.00 _cell_volume 895.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 886 _cell_measurement_theta_min 2.65 _cell_measurement_theta_max 25.89 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.810 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.179 _exptl_absorpt_correction_type none _exptl_special_details ; OXFORD low temperature device. ; _diffrn_ambient_temperature 93(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 SMART CCD area-detector' _diffrn_measurement_method '\w and \f scans' _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 5114 _diffrn_reflns_av_R_equivalents 0.0751 _diffrn_reflns_av_sigmaI/netI 0.0875 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.65 _diffrn_reflns_theta_max 28.08 _reflns_number_total 2028 _reflns_number_gt 1166 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution ; M.C. Burla, M. Camalli, B. Carrozzini, G.L. Cascarano, C. Giacovazzo, G. Polidori, R. Spagna (2003). SIR2002: the program. J. Appl. Cryst. 36,1103 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III (Burnett and Johnson, 1996), Mercury 1.4, CCDC' _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 'w=1/[\s^2^(Fo^2^)+(0.0315P)^2^] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2028 _refine_ls_number_parameters 170 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0794 _refine_ls_R_factor_gt 0.0432 _refine_ls_wR_factor_ref 0.0940 _refine_ls_wR_factor_gt 0.0836 _refine_ls_goodness_of_fit_ref 0.820 _refine_ls_restrained_S_all 0.820 _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 0.0708(4) 0.4807(4) 0.10550(7) 0.0200(5) Uani 1 1 d . . . C2 C 0.0042(4) 0.3477(3) 0.07024(7) 0.0189(5) Uani 1 1 d . . . C3 C 0.1419(4) 0.1421(4) 0.06306(7) 0.0231(5) Uani 1 1 d . . . C4 C 0.3400(4) 0.0716(4) 0.09113(7) 0.0234(5) Uani 1 1 d . . . C5 C 0.4127(4) 0.2043(3) 0.12775(7) 0.0203(5) Uani 1 1 d . . . C6 C 0.6180(4) 0.1387(3) 0.15744(7) 0.0234(5) Uani 1 1 d . . . C7 C 0.6903(4) 0.2708(4) 0.19189(7) 0.0252(5) Uani 1 1 d . . . C8 C 0.5555(4) 0.4749(4) 0.19913(7) 0.0255(5) Uani 1 1 d . . . C9 C 0.3543(4) 0.5430(4) 0.17139(7) 0.0228(5) Uani 1 1 d . . . C10 C 0.2768(4) 0.4123(3) 0.13513(7) 0.0196(5) Uani 1 1 d . . . C11 C -0.2105(4) 0.4185(3) 0.03898(7) 0.0207(5) Uani 1 1 d . . . F1 F 0.7508(2) -0.0581(2) 0.15124(4) 0.0308(4) Uani 1 1 d . . . F2 F 0.8894(2) 0.2066(2) 0.21958(4) 0.0343(4) Uani 1 1 d . . . F3 F 0.6313(2) 0.6015(2) 0.23335(4) 0.0354(4) Uani 1 1 d . . . F4 F 0.2257(2) 0.74013(19) 0.17975(4) 0.0279(3) Uani 1 1 d . . . O1 O -0.3447(3) 0.6006(2) 0.04872(5) 0.0266(4) Uani 1 1 d . . . O2 O -0.2580(3) 0.3050(2) 0.00554(5) 0.0257(4) Uani 1 1 d . . . H1 H -0.024(4) 0.616(4) 0.1101(7) 0.024(6) Uiso 1 1 d . . . H3 H 0.081(4) 0.057(3) 0.0389(7) 0.025(6) Uiso 1 1 d . . . H4 H 0.437(4) -0.065(4) 0.0852(7) 0.029(6) Uiso 1 1 d . . . H1O H -0.513(6) 0.630(5) 0.0247(10) 0.092(10) 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 C1 0.0219(12) 0.0195(12) 0.0186(12) 0.0015(9) -0.0009(9) 0.0015(9) C2 0.0203(11) 0.0216(11) 0.0147(12) 0.0023(9) -0.0015(9) 0.0001(8) C3 0.0267(13) 0.0234(12) 0.0190(13) -0.0032(10) -0.0022(10) 0.0011(9) C4 0.0258(12) 0.0213(12) 0.0231(13) -0.0020(10) -0.0039(10) 0.0028(10) C5 0.0212(11) 0.0228(12) 0.0170(12) 0.0041(9) -0.0008(9) -0.0011(9) C6 0.0223(12) 0.0252(12) 0.0228(13) 0.0040(10) -0.0006(10) 0.0036(9) C7 0.0185(11) 0.0353(14) 0.0216(13) 0.0089(11) -0.0039(10) 0.0006(10) C8 0.0280(13) 0.0321(13) 0.0160(12) -0.0031(10) -0.0052(10) -0.0060(10) C9 0.0245(12) 0.0229(12) 0.0208(13) 0.0001(10) -0.0016(10) 0.0018(9) C10 0.0198(11) 0.0231(12) 0.0159(12) 0.0016(9) -0.0015(9) -0.0025(9) C11 0.0219(11) 0.0231(12) 0.0171(12) 0.0012(10) -0.0003(9) 0.0012(9) F1 0.0327(8) 0.0248(7) 0.0349(8) 0.0002(6) -0.0018(6) 0.0126(5) F2 0.0295(7) 0.0476(9) 0.0255(8) 0.0043(6) -0.0119(6) 0.0057(6) F3 0.0390(8) 0.0427(8) 0.0241(8) -0.0100(6) -0.0135(6) 0.0031(6) F4 0.0306(7) 0.0247(7) 0.0280(8) -0.0054(5) -0.0100(6) 0.0073(5) O1 0.0288(9) 0.0286(9) 0.0221(9) -0.0040(7) -0.0076(7) 0.0092(7) O2 0.0292(9) 0.0305(9) 0.0173(9) -0.0046(7) -0.0069(7) 0.0041(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 C2 1.373(3) . ? C1 C10 1.414(3) . ? C1 H1 0.94(2) . ? C2 C3 1.410(3) . ? C2 C11 1.480(3) . ? C3 C4 1.360(3) . ? C3 H3 0.94(2) . ? C4 C5 1.412(3) . ? C4 H4 0.96(2) . ? C5 C6 1.408(3) . ? C5 C10 1.419(3) . ? C6 F1 1.349(2) . ? C6 C7 1.358(3) . ? C7 F2 1.345(2) . ? C7 C8 1.396(3) . ? C8 F3 1.338(2) . ? C8 C9 1.360(3) . ? C9 F4 1.352(2) . ? C9 C10 1.403(3) . ? C11 O2 1.245(2) . ? C11 O1 1.300(2) . ? O1 H1O 1.12(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 C2 C1 C10 120.4(2) . . ? C2 C1 H1 119.3(12) . . ? C10 C1 H1 120.3(12) . . ? C1 C2 C3 120.32(19) . . ? C1 C2 C11 120.70(19) . . ? C3 C2 C11 118.98(19) . . ? C4 C3 C2 120.6(2) . . ? C4 C3 H3 123.5(12) . . ? C2 C3 H3 115.8(12) . . ? C3 C4 C5 120.4(2) . . ? C3 C4 H4 119.6(12) . . ? C5 C4 H4 119.9(12) . . ? C6 C5 C4 122.31(19) . . ? C6 C5 C10 118.23(19) . . ? C4 C5 C10 119.45(18) . . ? F1 C6 C7 118.81(18) . . ? F1 C6 C5 119.54(19) . . ? C7 C6 C5 121.6(2) . . ? F2 C7 C6 120.8(2) . . ? F2 C7 C8 119.3(2) . . ? C6 C7 C8 119.95(19) . . ? F3 C8 C9 121.3(2) . . ? F3 C8 C7 118.58(18) . . ? C9 C8 C7 120.1(2) . . ? F4 C9 C8 118.46(19) . . ? F4 C9 C10 120.02(18) . . ? C8 C9 C10 121.5(2) . . ? C9 C10 C1 122.6(2) . . ? C9 C10 C5 118.56(18) . . ? C1 C10 C5 118.83(19) . . ? O2 C11 O1 122.97(18) . . ? O2 C11 C2 120.45(19) . . ? O1 C11 C2 116.58(18) . . ? C11 O1 H1O 110.7(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 C10 C1 C2 C3 -0.4(3) . . . . ? C10 C1 C2 C11 -179.75(18) . . . . ? C1 C2 C3 C4 0.7(3) . . . . ? C11 C2 C3 C4 -179.9(2) . . . . ? C2 C3 C4 C5 -0.6(3) . . . . ? C3 C4 C5 C6 -179.5(2) . . . . ? C3 C4 C5 C10 0.1(3) . . . . ? C4 C5 C6 F1 -0.4(3) . . . . ? C10 C5 C6 F1 -179.95(18) . . . . ? C4 C5 C6 C7 178.3(2) . . . . ? C10 C5 C6 C7 -1.3(3) . . . . ? F1 C6 C7 F2 -0.5(3) . . . . ? C5 C6 C7 F2 -179.12(18) . . . . ? F1 C6 C7 C8 -179.77(19) . . . . ? C5 C6 C7 C8 1.6(3) . . . . ? F2 C7 C8 F3 0.7(3) . . . . ? C6 C7 C8 F3 180.0(2) . . . . ? F2 C7 C8 C9 179.77(19) . . . . ? C6 C7 C8 C9 -0.9(3) . . . . ? F3 C8 C9 F4 -1.8(3) . . . . ? C7 C8 C9 F4 179.14(19) . . . . ? F3 C8 C9 C10 179.08(19) . . . . ? C7 C8 C9 C10 0.0(3) . . . . ? F4 C9 C10 C1 1.7(3) . . . . ? C8 C9 C10 C1 -179.2(2) . . . . ? F4 C9 C10 C5 -178.88(18) . . . . ? C8 C9 C10 C5 0.2(3) . . . . ? C2 C1 C10 C9 179.3(2) . . . . ? C2 C1 C10 C5 -0.1(3) . . . . ? C6 C5 C10 C9 0.4(3) . . . . ? C4 C5 C10 C9 -179.2(2) . . . . ? C6 C5 C10 C1 179.82(19) . . . . ? C4 C5 C10 C1 0.2(3) . . . . ? C1 C2 C11 O2 175.3(2) . . . . ? C3 C2 C11 O2 -4.1(3) . . . . ? C1 C2 C11 O1 -5.5(3) . . . . ? C3 C2 C11 O1 175.13(19) . . . . ? _diffrn_measured_fraction_theta_max 0.929 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.355 _refine_diff_density_min -0.240 _refine_diff_density_rms 0.058 data_cz7_295k _database_code_depnum_ccdc_archive 'CCDC 697373' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H4 F4 O2' _chemical_formula_sum 'C11 H4 F4 O2' _chemical_formula_weight 244.14 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' 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 5.053(2) _cell_length_b 5.884(2) _cell_length_c 31.085(12) _cell_angle_alpha 90.00 _cell_angle_beta 92.830(10) _cell_angle_gamma 90.00 _cell_volume 923.1(6) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 1682 _cell_measurement_theta_min 2.63 _cell_measurement_theta_max 23.91 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.757 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.173 _exptl_absorpt_correction_type none _exptl_special_details ; Air conditioned room ; _diffrn_ambient_temperature 295(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 SMART CCD area-detector' _diffrn_measurement_method '\w and \f scans' _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 6629 _diffrn_reflns_av_R_equivalents 0.0774 _diffrn_reflns_av_sigmaI/netI 0.0529 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 2.62 _diffrn_reflns_theta_max 25.49 _reflns_number_total 1716 _reflns_number_gt 1080 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution ; M.C. Burla, M. Camalli, B. Carrozzini, G.L. Cascarano, C. Giacovazzo, G. Polidori, R. Spagna (2003). SIR2002: the program. J. Appl. Cryst. 36,1103 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III (Burnett and Johnson, 1996), Mercury 1.4, CCDC' _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 'w=1/[\s^2^(Fo^2^)+(0.0478P)^2^] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1716 _refine_ls_number_parameters 170 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0616 _refine_ls_R_factor_gt 0.0368 _refine_ls_wR_factor_ref 0.1014 _refine_ls_wR_factor_gt 0.0914 _refine_ls_goodness_of_fit_ref 0.946 _refine_ls_restrained_S_all 0.946 _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 0.0710(4) 0.4752(3) 0.10544(6) 0.0454(5) Uani 1 1 d . . . C2 C 0.0050(3) 0.3454(3) 0.06998(5) 0.0445(5) Uani 1 1 d . . . C3 C 0.1415(4) 0.1424(4) 0.06271(7) 0.0558(6) Uani 1 1 d . . . C4 C 0.3412(4) 0.0735(4) 0.09038(7) 0.0574(6) Uani 1 1 d . . . C5 C 0.4144(4) 0.2033(3) 0.12706(6) 0.0458(5) Uani 1 1 d . . . C6 C 0.6204(4) 0.1394(4) 0.15648(6) 0.0540(5) Uani 1 1 d . . . C7 C 0.6906(4) 0.2679(4) 0.19112(7) 0.0577(6) Uani 1 1 d . . . C8 C 0.5555(4) 0.4680(4) 0.19873(6) 0.0576(6) Uani 1 1 d . . . C9 C 0.3547(4) 0.5351(3) 0.17144(6) 0.0524(5) Uani 1 1 d . . . C10 C 0.2777(3) 0.4074(3) 0.13473(6) 0.0427(5) Uani 1 1 d . . . C11 C -0.2115(4) 0.4166(3) 0.03927(6) 0.0480(5) Uani 1 1 d . . . F1 F 0.7547(2) -0.0548(2) 0.14987(4) 0.0788(5) Uani 1 1 d . . . F2 F 0.8904(2) 0.2053(2) 0.21858(4) 0.0848(5) Uani 1 1 d . . . F3 F 0.6289(3) 0.5920(2) 0.23335(4) 0.0867(5) Uani 1 1 d . . . F4 F 0.2247(2) 0.72929(19) 0.17987(4) 0.0718(4) Uani 1 1 d . . . O1 O -0.3404(3) 0.5962(2) 0.04785(4) 0.0645(5) Uani 1 1 d . . . O2 O -0.2618(3) 0.3002(3) 0.00617(4) 0.0648(4) Uani 1 1 d . . . H1 H -0.020(4) 0.609(3) 0.1100(6) 0.056(6) Uiso 1 1 d . . . H1O H -0.528(6) 0.642(5) 0.0217(10) 0.145(11) Uiso 1 1 d . . . H3 H 0.087(4) 0.057(3) 0.0385(7) 0.066(6) Uiso 1 1 d . . . H4 H 0.438(4) -0.057(4) 0.0848(6) 0.070(6) 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 C1 0.0468(11) 0.0464(12) 0.0422(11) -0.0007(9) -0.0048(9) 0.0072(9) C2 0.0453(10) 0.0492(11) 0.0382(10) -0.0017(9) -0.0044(8) 0.0063(9) C3 0.0610(13) 0.0571(13) 0.0481(12) -0.0109(11) -0.0103(10) 0.0093(10) C4 0.0618(13) 0.0523(13) 0.0570(14) -0.0056(11) -0.0077(11) 0.0160(11) C5 0.0446(10) 0.0496(11) 0.0429(11) 0.0050(9) -0.0014(9) 0.0042(9) C6 0.0482(11) 0.0594(13) 0.0537(13) 0.0089(10) -0.0039(10) 0.0126(10) C7 0.0434(11) 0.0801(16) 0.0482(13) 0.0120(11) -0.0110(9) 0.0060(10) C8 0.0560(12) 0.0743(15) 0.0410(12) -0.0038(10) -0.0128(10) -0.0024(11) C9 0.0534(12) 0.0556(13) 0.0474(12) -0.0041(10) -0.0071(10) 0.0059(10) C10 0.0427(10) 0.0466(11) 0.0385(10) 0.0026(9) -0.0024(8) 0.0011(8) C11 0.0482(11) 0.0550(13) 0.0403(11) -0.0040(10) -0.0034(9) 0.0064(10) F1 0.0769(9) 0.0738(9) 0.0841(10) 0.0011(7) -0.0121(7) 0.0369(7) F2 0.0650(8) 0.1176(11) 0.0684(9) 0.0099(7) -0.0297(7) 0.0192(7) F3 0.0859(9) 0.1089(11) 0.0618(8) -0.0251(7) -0.0331(7) 0.0099(7) F4 0.0789(8) 0.0654(8) 0.0682(8) -0.0209(6) -0.0255(7) 0.0226(6) O1 0.0663(9) 0.0706(10) 0.0546(9) -0.0122(7) -0.0185(7) 0.0253(8) O2 0.0672(9) 0.0782(10) 0.0468(8) -0.0172(7) -0.0189(7) 0.0194(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 C2 1.369(2) . ? C1 C10 1.409(2) . ? C1 H1 0.92(2) . ? C2 C3 1.404(3) . ? C2 C11 1.476(2) . ? C3 C4 1.356(3) . ? C3 H3 0.94(2) . ? C4 C5 1.407(3) . ? C4 H4 0.93(2) . ? C5 C6 1.403(2) . ? C5 C10 1.411(3) . ? C6 C7 1.349(3) . ? C6 F1 1.350(2) . ? C7 F2 1.341(2) . ? C7 C8 1.387(3) . ? C8 F3 1.338(2) . ? C8 C9 1.349(2) . ? C9 F4 1.350(2) . ? C9 C10 1.405(3) . ? C11 O2 1.252(2) . ? C11 O1 1.277(2) . ? O1 H1O 1.25(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 C2 C1 C10 120.38(18) . . ? C2 C1 H1 119.6(11) . . ? C10 C1 H1 120.0(11) . . ? C1 C2 C3 120.16(17) . . ? C1 C2 C11 120.39(17) . . ? C3 C2 C11 119.44(17) . . ? C4 C3 C2 120.60(19) . . ? C4 C3 H3 121.9(12) . . ? C2 C3 H3 117.5(12) . . ? C3 C4 C5 120.6(2) . . ? C3 C4 H4 120.7(12) . . ? C5 C4 H4 118.6(12) . . ? C6 C5 C4 122.66(18) . . ? C6 C5 C10 118.13(18) . . ? C4 C5 C10 119.20(17) . . ? C7 C6 F1 118.79(16) . . ? C7 C6 C5 121.85(19) . . ? F1 C6 C5 119.35(18) . . ? F2 C7 C6 120.94(19) . . ? F2 C7 C8 119.07(19) . . ? C6 C7 C8 119.99(17) . . ? F3 C8 C9 121.10(19) . . ? F3 C8 C7 118.75(17) . . ? C9 C8 C7 120.16(18) . . ? C8 C9 F4 118.93(18) . . ? C8 C9 C10 121.58(19) . . ? F4 C9 C10 119.49(16) . . ? C9 C10 C1 122.69(18) . . ? C9 C10 C5 118.29(16) . . ? C1 C10 C5 119.02(17) . . ? O2 C11 O1 122.66(16) . . ? O2 C11 C2 119.36(18) . . ? O1 C11 C2 117.98(16) . . ? C11 O1 H1O 114.9(13) . . ? 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 C10 C1 C2 C3 0.5(3) . . . . ? C10 C1 C2 C11 -179.97(17) . . . . ? C1 C2 C3 C4 -0.6(3) . . . . ? C11 C2 C3 C4 179.90(19) . . . . ? C2 C3 C4 C5 0.4(3) . . . . ? C3 C4 C5 C6 -179.7(2) . . . . ? C3 C4 C5 C10 -0.2(3) . . . . ? C4 C5 C6 C7 178.9(2) . . . . ? C10 C5 C6 C7 -0.6(3) . . . . ? C4 C5 C6 F1 -0.4(3) . . . . ? C10 C5 C6 F1 -179.90(17) . . . . ? F1 C6 C7 F2 0.2(3) . . . . ? C5 C6 C7 F2 -179.13(18) . . . . ? F1 C6 C7 C8 -179.84(19) . . . . ? C5 C6 C7 C8 0.8(3) . . . . ? F2 C7 C8 F3 -0.1(3) . . . . ? C6 C7 C8 F3 179.91(19) . . . . ? F2 C7 C8 C9 179.63(19) . . . . ? C6 C7 C8 C9 -0.3(3) . . . . ? F3 C8 C9 F4 -1.0(3) . . . . ? C7 C8 C9 F4 179.29(18) . . . . ? F3 C8 C9 C10 179.33(19) . . . . ? C7 C8 C9 C10 -0.4(3) . . . . ? C8 C9 C10 C1 -179.18(19) . . . . ? F4 C9 C10 C1 1.1(3) . . . . ? C8 C9 C10 C5 0.7(3) . . . . ? F4 C9 C10 C5 -179.04(17) . . . . ? C2 C1 C10 C9 179.51(18) . . . . ? C2 C1 C10 C5 -0.3(3) . . . . ? C6 C5 C10 C9 -0.2(3) . . . . ? C4 C5 C10 C9 -179.70(19) . . . . ? C6 C5 C10 C1 179.68(17) . . . . ? C4 C5 C10 C1 0.1(3) . . . . ? C1 C2 C11 O2 177.19(19) . . . . ? C3 C2 C11 O2 -3.3(3) . . . . ? C1 C2 C11 O1 -2.8(3) . . . . ? C3 C2 C11 O1 176.66(17) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.169 _refine_diff_density_min -0.164 _refine_diff_density_rms 0.036 data_cz10_295k _database_code_depnum_ccdc_archive 'CCDC 697374' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H5 F4 N O' _chemical_formula_sum 'C11 H5 F4 N O' _chemical_formula_weight 243.16 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 4.9553(10) _cell_length_b 7.3353(15) _cell_length_c 13.504(3) _cell_angle_alpha 96.420(10) _cell_angle_beta 97.360(10) _cell_angle_gamma 100.810(10) _cell_volume 473.50(17) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 1143 _cell_measurement_theta_min 2.86 _cell_measurement_theta_max 25.13 _exptl_crystal_description table _exptl_crystal_colour colourless _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.706 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 244 _exptl_absorpt_coefficient_mu 0.164 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS, Bruker, 1997' _exptl_absorpt_correction_T_min 0.743709 _exptl_absorpt_correction_T_max 1.000000 _exptl_special_details ; OXFORD low temperature device. ; _diffrn_ambient_temperature 295(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 SMART CCD area-detector' _diffrn_measurement_method '\w and \f scans' _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 3650 _diffrn_reflns_av_R_equivalents 0.0140 _diffrn_reflns_av_sigmaI/netI 0.0211 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.85 _diffrn_reflns_theta_max 25.99 _reflns_number_total 1807 _reflns_number_gt 1297 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution ; M.C. Burla, M. Camalli, B. Carrozzini, G.L. Cascarano, C. Giacovazzo, G. Polidori, R. Spagna (2003). SIR2002: the program. J. Appl. Cryst. 36,1103 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III (Burnett and Johnson, 1996), Mercury 1.4, CCDC' _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 'w=1/[\s^2^(Fo^2^)+(0.0582P)^2^+0.0315P] 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 refall _refine_ls_extinction_method none _refine_ls_number_reflns 1807 _refine_ls_number_parameters 174 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0561 _refine_ls_R_factor_gt 0.0379 _refine_ls_wR_factor_ref 0.1093 _refine_ls_wR_factor_gt 0.0970 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _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 1.1577(3) 1.49036(16) 0.71879(10) 0.0864(4) Uani 1 1 d . . . F2 F 0.7200(3) 1.48597(18) 0.57705(10) 0.0985(5) Uani 1 1 d . . . F3 F 0.2970(2) 1.18524(18) 0.53247(9) 0.0838(4) Uani 1 1 d . . . F4 F 0.3077(2) 0.88176(17) 0.62790(9) 0.0739(4) Uani 1 1 d . . . O1 O 1.2193(2) 0.68816(17) 0.94636(10) 0.0589(4) Uani 1 1 d . . . N1 N 0.7538(3) 0.6010(2) 0.91933(12) 0.0510(4) Uani 1 1 d . . . C1 C 0.7499(3) 0.8734(3) 0.78020(13) 0.0459(4) Uani 1 1 d . . . C2 C 0.9698(3) 0.8761(2) 0.85358(12) 0.0437(4) Uani 1 1 d . . . C3 C 1.1884(4) 1.0349(2) 0.87607(14) 0.0494(4) Uani 1 1 d . . . C4 C 1.1840(4) 1.1857(3) 0.82737(14) 0.0537(5) Uani 1 1 d . . . C5 C 0.9596(3) 1.1868(2) 0.75165(13) 0.0485(4) Uani 1 1 d . . . C6 C 0.9471(4) 1.3403(3) 0.69847(15) 0.0599(5) Uani 1 1 d . . . C7 C 0.7288(4) 1.3386(3) 0.62647(15) 0.0656(6) Uani 1 1 d . . . C8 C 0.5114(4) 1.1823(3) 0.60298(13) 0.0621(5) Uani 1 1 d . . . C9 C 0.5193(4) 1.0318(3) 0.65148(13) 0.0543(5) Uani 1 1 d . . . C10 C 0.7405(3) 1.0272(2) 0.72731(12) 0.0464(4) Uani 1 1 d . . . C11 C 0.9888(3) 0.7146(2) 0.91005(12) 0.0448(4) Uani 1 1 d . . . H1 H 0.616(4) 0.772(3) 0.7627(13) 0.050(5) Uiso 1 1 d . . . H3 H 1.337(4) 1.033(2) 0.9282(13) 0.057(5) Uiso 1 1 d . . . H1N H 0.772(4) 0.514(3) 0.9599(14) 0.055(5) Uiso 1 1 d . . . H2N H 0.598(4) 0.637(3) 0.9047(15) 0.075(6) Uiso 1 1 d . . . H4 H 1.334(3) 1.293(2) 0.8432(12) 0.050(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 F1 0.0978(9) 0.0540(7) 0.1002(9) 0.0295(6) -0.0010(7) -0.0030(6) F2 0.1264(11) 0.0795(9) 0.0977(10) 0.0499(7) -0.0013(8) 0.0318(8) F3 0.0815(9) 0.1035(10) 0.0713(8) 0.0318(7) -0.0099(6) 0.0346(7) F4 0.0553(7) 0.0831(8) 0.0763(8) 0.0229(6) -0.0118(5) 0.0043(6) O1 0.0340(6) 0.0683(8) 0.0829(9) 0.0361(7) 0.0089(5) 0.0168(5) N1 0.0349(8) 0.0539(9) 0.0691(10) 0.0269(8) 0.0068(7) 0.0115(7) C1 0.0376(9) 0.0466(10) 0.0537(10) 0.0119(8) 0.0051(7) 0.0080(8) C2 0.0379(8) 0.0464(9) 0.0506(9) 0.0122(7) 0.0093(7) 0.0135(7) C3 0.0409(9) 0.0520(10) 0.0542(10) 0.0128(8) 0.0010(8) 0.0082(8) C4 0.0487(10) 0.0473(11) 0.0613(11) 0.0113(8) 0.0023(8) 0.0019(8) C5 0.0520(10) 0.0466(10) 0.0500(9) 0.0104(7) 0.0095(8) 0.0143(8) C6 0.0701(13) 0.0486(11) 0.0628(11) 0.0155(9) 0.0106(9) 0.0118(9) C7 0.0835(14) 0.0584(12) 0.0633(12) 0.0250(10) 0.0108(11) 0.0266(11) C8 0.0642(12) 0.0774(14) 0.0515(11) 0.0196(10) 0.0024(9) 0.0295(11) C9 0.0477(10) 0.0621(12) 0.0532(10) 0.0126(9) 0.0031(8) 0.0122(9) C10 0.0452(9) 0.0487(10) 0.0486(9) 0.0112(7) 0.0092(7) 0.0143(8) C11 0.0374(9) 0.0507(10) 0.0509(9) 0.0130(8) 0.0087(7) 0.0164(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 C6 1.343(2) . ? F2 C7 1.337(2) . ? F3 C8 1.338(2) . ? F4 C9 1.348(2) . ? O1 C11 1.2421(18) . ? N1 C11 1.328(2) . ? N1 H1N 0.895(19) . ? N1 H2N 0.87(2) . ? C1 C2 1.371(2) . ? C1 C10 1.406(2) . ? C1 H1 0.883(18) . ? C2 C3 1.409(2) . ? C2 C11 1.490(2) . ? C3 C4 1.351(3) . ? C3 H3 0.953(18) . ? C4 C5 1.413(2) . ? C4 H4 0.958(18) . ? C5 C6 1.408(3) . ? C5 C10 1.416(2) . ? C6 C7 1.356(3) . ? C7 C8 1.394(3) . ? C8 C9 1.349(3) . ? C9 C10 1.409(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 C11 N1 H1N 115.3(11) . . ? C11 N1 H2N 118.4(14) . . ? H1N N1 H2N 122.7(18) . . ? C2 C1 C10 120.69(17) . . ? C2 C1 H1 120.5(11) . . ? C10 C1 H1 118.7(11) . . ? C1 C2 C3 119.54(16) . . ? C1 C2 C11 122.16(15) . . ? C3 C2 C11 118.29(14) . . ? C4 C3 C2 121.19(17) . . ? C4 C3 H3 121.3(11) . . ? C2 C3 H3 117.5(11) . . ? C3 C4 C5 120.44(17) . . ? C3 C4 H4 120.3(10) . . ? C5 C4 H4 119.2(10) . . ? C6 C5 C4 122.43(17) . . ? C6 C5 C10 118.61(16) . . ? C4 C5 C10 118.96(15) . . ? F1 C6 C7 119.45(17) . . ? F1 C6 C5 119.17(17) . . ? C7 C6 C5 121.37(18) . . ? F2 C7 C6 120.51(19) . . ? F2 C7 C8 119.32(18) . . ? C6 C7 C8 120.17(17) . . ? F3 C8 C9 121.18(19) . . ? F3 C8 C7 118.92(17) . . ? C9 C8 C7 119.90(17) . . ? F4 C9 C8 119.20(16) . . ? F4 C9 C10 118.68(15) . . ? C8 C9 C10 122.11(17) . . ? C1 C10 C9 123.00(16) . . ? C1 C10 C5 119.17(15) . . ? C9 C10 C5 117.83(16) . . ? O1 C11 N1 121.74(15) . . ? O1 C11 C2 120.25(14) . . ? N1 C11 C2 118.00(14) . . ? 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 C10 C1 C2 C3 0.0(3) . . . . ? C10 C1 C2 C11 -179.04(14) . . . . ? C1 C2 C3 C4 0.7(3) . . . . ? C11 C2 C3 C4 179.82(16) . . . . ? C2 C3 C4 C5 -0.6(3) . . . . ? C3 C4 C5 C6 -179.57(17) . . . . ? C3 C4 C5 C10 -0.3(3) . . . . ? C4 C5 C6 F1 1.2(3) . . . . ? C10 C5 C6 F1 -178.05(15) . . . . ? C4 C5 C6 C7 -179.62(17) . . . . ? C10 C5 C6 C7 1.1(3) . . . . ? F1 C6 C7 F2 -1.1(3) . . . . ? C5 C6 C7 F2 179.72(17) . . . . ? F1 C6 C7 C8 178.63(17) . . . . ? C5 C6 C7 C8 -0.6(3) . . . . ? F2 C7 C8 F3 -1.1(3) . . . . ? C6 C7 C8 F3 179.22(17) . . . . ? F2 C7 C8 C9 179.23(17) . . . . ? C6 C7 C8 C9 -0.5(3) . . . . ? F3 C8 C9 F4 0.3(3) . . . . ? C7 C8 C9 F4 -179.97(16) . . . . ? F3 C8 C9 C10 -178.76(16) . . . . ? C7 C8 C9 C10 1.0(3) . . . . ? C2 C1 C10 C9 -179.85(15) . . . . ? C2 C1 C10 C5 -0.9(3) . . . . ? F4 C9 C10 C1 -0.5(3) . . . . ? C8 C9 C10 C1 178.62(17) . . . . ? F4 C9 C10 C5 -179.43(15) . . . . ? C8 C9 C10 C5 -0.4(3) . . . . ? C6 C5 C10 C1 -179.69(15) . . . . ? C4 C5 C10 C1 1.0(3) . . . . ? C6 C5 C10 C9 -0.7(3) . . . . ? C4 C5 C10 C9 -179.95(16) . . . . ? C1 C2 C11 O1 153.23(17) . . . . ? C3 C2 C11 O1 -25.8(2) . . . . ? C1 C2 C11 N1 -26.3(2) . . . . ? C3 C2 C11 N1 154.59(16) . . . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.143 _refine_diff_density_min -0.159 _refine_diff_density_rms 0.033 data_cz10_93k _database_code_depnum_ccdc_archive 'CCDC 697375' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H5 F4 N O' _chemical_formula_sum 'C11 H5 F4 N O' _chemical_formula_weight 243.16 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 4.9386(14) _cell_length_b 7.250(2) _cell_length_c 13.210(4) _cell_angle_alpha 97.630(10) _cell_angle_beta 96.440(10) _cell_angle_gamma 100.470(10) _cell_volume 456.5(2) _cell_formula_units_Z 2 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 954 _cell_measurement_theta_min 2.89 _cell_measurement_theta_max 27.46 _exptl_crystal_description table _exptl_crystal_colour colourless _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.46 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.769 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 244 _exptl_absorpt_coefficient_mu 0.170 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS, Bruker, 1997' _exptl_absorpt_correction_T_min 0.718937 _exptl_absorpt_correction_T_max 1.000000 _exptl_special_details ; OXFORD low temperature device. ; _diffrn_ambient_temperature 93(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 SMART CCD area-detector' _diffrn_measurement_method '\w and \f scans' _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 3898 _diffrn_reflns_av_R_equivalents 0.0254 _diffrn_reflns_av_sigmaI/netI 0.0414 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.89 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2002 _reflns_number_gt 1393 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution ; M.C. Burla, M. Camalli, B. Carrozzini, G.L. Cascarano, C. Giacovazzo, G. Polidori, R. Spagna (2003). SIR2002: the program. J. Appl. Cryst. 36,1103 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III (Burnett and Johnson, 1996), Mercury 1.4, CCDC' _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 'w=1/[\s^2^(Fo^2^)+(0.0801P)^2^] 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 refall _refine_ls_extinction_method none _refine_ls_number_reflns 2002 _refine_ls_number_parameters 174 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0722 _refine_ls_R_factor_gt 0.0489 _refine_ls_wR_factor_ref 0.1422 _refine_ls_wR_factor_gt 0.1250 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _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 1.1669(3) 1.49627(17) 0.71651(10) 0.0339(4) Uani 1 1 d . . . F2 F 0.7267(3) 1.49253(18) 0.57456(10) 0.0364(4) Uani 1 1 d . . . F3 F 0.2989(2) 1.19107(17) 0.53116(9) 0.0320(4) Uani 1 1 d . . . F4 F 0.3096(2) 0.88368(17) 0.62635(9) 0.0300(3) Uani 1 1 d . . . O1 O 1.2226(3) 0.6886(2) 0.94687(11) 0.0265(4) Uani 1 1 d . . . N1 N 0.7557(4) 0.5995(3) 0.91809(14) 0.0235(4) Uani 1 1 d . . . C1 C 0.7529(4) 0.8746(3) 0.77928(16) 0.0220(5) Uani 1 1 d . . . C2 C 0.9733(4) 0.8777(3) 0.85287(16) 0.0228(5) Uani 1 1 d . . . C3 C 1.1949(4) 1.0371(3) 0.87598(16) 0.0229(5) Uani 1 1 d . . . C4 C 1.1918(4) 1.1898(3) 0.82648(16) 0.0251(5) Uani 1 1 d . . . C5 C 0.9662(4) 1.1907(3) 0.75022(16) 0.0229(5) Uani 1 1 d . . . C6 C 0.9545(4) 1.3449(3) 0.69634(17) 0.0260(5) Uani 1 1 d . . . C7 C 0.7352(5) 1.3441(3) 0.62425(16) 0.0274(5) Uani 1 1 d . . . C8 C 0.5155(4) 1.1873(3) 0.60104(15) 0.0259(5) Uani 1 1 d . . . C9 C 0.5227(4) 1.0344(3) 0.65012(16) 0.0243(5) Uani 1 1 d . . . C10 C 0.7453(4) 1.0299(3) 0.72591(15) 0.0219(5) Uani 1 1 d . . . C11 C 0.9925(4) 0.7145(3) 0.90994(15) 0.0223(5) Uani 1 1 d . . . H1 H 0.627(5) 0.773(3) 0.7640(16) 0.020(6) Uiso 1 1 d . . . H3 H 1.344(4) 1.033(3) 0.9285(16) 0.021(5) Uiso 1 1 d . . . H1N H 0.774(5) 0.513(3) 0.9566(18) 0.025(6) Uiso 1 1 d . . . H2N H 0.605(5) 0.638(3) 0.9056(18) 0.030(6) Uiso 1 1 d . . . H4 H 1.350(4) 1.298(3) 0.8421(15) 0.017(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 F1 0.0345(8) 0.0238(7) 0.0406(8) 0.0079(6) -0.0007(6) 0.0000(6) F2 0.0421(8) 0.0297(8) 0.0394(8) 0.0141(6) -0.0007(6) 0.0101(6) F3 0.0283(7) 0.0376(8) 0.0314(7) 0.0083(6) -0.0017(5) 0.0114(6) F4 0.0225(7) 0.0304(7) 0.0348(7) 0.0057(5) -0.0009(5) 0.0022(5) O1 0.0169(7) 0.0301(9) 0.0341(8) 0.0097(7) 0.0030(6) 0.0057(6) N1 0.0165(9) 0.0233(10) 0.0324(10) 0.0085(8) 0.0022(7) 0.0061(7) C1 0.0175(11) 0.0208(11) 0.0267(11) -0.0007(9) 0.0039(8) 0.0038(9) C2 0.0199(10) 0.0242(11) 0.0257(11) 0.0023(9) 0.0067(8) 0.0071(8) C3 0.0179(10) 0.0256(11) 0.0247(11) 0.0016(9) 0.0026(8) 0.0047(8) C4 0.0214(11) 0.0227(11) 0.0290(12) -0.0018(9) 0.0036(9) 0.0029(9) C5 0.0229(11) 0.0220(11) 0.0245(10) 0.0007(8) 0.0066(8) 0.0063(9) C6 0.0267(12) 0.0206(11) 0.0304(12) 0.0017(9) 0.0080(9) 0.0027(9) C7 0.0324(12) 0.0240(11) 0.0287(12) 0.0073(9) 0.0063(10) 0.0095(10) C8 0.0238(11) 0.0329(12) 0.0225(11) 0.0024(9) 0.0020(8) 0.0119(9) C9 0.0195(10) 0.0278(12) 0.0248(11) 0.0010(9) 0.0047(8) 0.0038(9) C10 0.0192(10) 0.0235(11) 0.0239(11) 0.0014(8) 0.0067(8) 0.0058(9) C11 0.0201(11) 0.0254(11) 0.0217(10) -0.0002(8) 0.0035(8) 0.0074(9) _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 C6 1.348(2) . ? F2 C7 1.337(2) . ? F3 C8 1.339(2) . ? F4 C9 1.348(2) . ? O1 C11 1.242(2) . ? N1 C11 1.331(3) . ? N1 H1N 0.87(2) . ? N1 H2N 0.85(2) . ? C1 C2 1.370(3) . ? C1 C10 1.409(3) . ? C1 H1 0.86(2) . ? C2 C3 1.414(3) . ? C2 C11 1.496(3) . ? C3 C4 1.360(3) . ? C3 H3 0.96(2) . ? C4 C5 1.417(3) . ? C4 H4 0.98(2) . ? C5 C6 1.409(3) . ? C5 C10 1.419(3) . ? C6 C7 1.358(3) . ? C7 C8 1.396(3) . ? C8 C9 1.360(3) . ? C9 C10 1.410(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 H1N 114.7(15) . . ? C11 N1 H2N 118.2(16) . . ? H1N N1 H2N 123(2) . . ? C2 C1 C10 120.4(2) . . ? C2 C1 H1 117.9(14) . . ? C10 C1 H1 121.6(14) . . ? C1 C2 C3 120.18(19) . . ? C1 C2 C11 122.16(19) . . ? C3 C2 C11 117.65(18) . . ? C4 C3 C2 120.7(2) . . ? C4 C3 H3 121.9(13) . . ? C2 C3 H3 117.3(12) . . ? C3 C4 C5 120.3(2) . . ? C3 C4 H4 119.7(12) . . ? C5 C4 H4 120.0(11) . . ? C6 C5 C4 122.4(2) . . ? C6 C5 C10 118.51(19) . . ? C4 C5 C10 119.08(19) . . ? F1 C6 C7 119.29(18) . . ? F1 C6 C5 119.13(19) . . ? C7 C6 C5 121.6(2) . . ? F2 C7 C6 120.70(19) . . ? F2 C7 C8 119.18(18) . . ? C6 C7 C8 120.12(19) . . ? F3 C8 C9 121.1(2) . . ? F3 C8 C7 119.11(18) . . ? C9 C8 C7 119.83(19) . . ? F4 C9 C8 119.06(18) . . ? F4 C9 C10 119.05(18) . . ? C8 C9 C10 121.9(2) . . ? C1 C10 C9 122.6(2) . . ? C1 C10 C5 119.32(19) . . ? C9 C10 C5 118.05(19) . . ? O1 C11 N1 122.21(18) . . ? O1 C11 C2 120.35(18) . . ? N1 C11 C2 117.43(18) . . ? 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 C10 C1 C2 C3 0.1(3) . . . . ? C10 C1 C2 C11 -178.81(18) . . . . ? C1 C2 C3 C4 0.6(3) . . . . ? C11 C2 C3 C4 179.55(18) . . . . ? C2 C3 C4 C5 -0.4(3) . . . . ? C3 C4 C5 C6 -179.5(2) . . . . ? C3 C4 C5 C10 -0.4(3) . . . . ? C4 C5 C6 F1 1.1(3) . . . . ? C10 C5 C6 F1 -178.07(17) . . . . ? C4 C5 C6 C7 -179.3(2) . . . . ? C10 C5 C6 C7 1.6(3) . . . . ? F1 C6 C7 F2 -0.9(3) . . . . ? C5 C6 C7 F2 179.41(19) . . . . ? F1 C6 C7 C8 178.91(19) . . . . ? C5 C6 C7 C8 -0.7(3) . . . . ? F2 C7 C8 F3 -1.4(3) . . . . ? C6 C7 C8 F3 178.72(19) . . . . ? F2 C7 C8 C9 179.25(18) . . . . ? C6 C7 C8 C9 -0.6(3) . . . . ? F3 C8 C9 F4 1.1(3) . . . . ? C7 C8 C9 F4 -179.61(18) . . . . ? F3 C8 C9 C10 -178.25(18) . . . . ? C7 C8 C9 C10 1.1(3) . . . . ? C2 C1 C10 C9 -179.53(19) . . . . ? C2 C1 C10 C5 -0.9(3) . . . . ? F4 C9 C10 C1 -0.9(3) . . . . ? C8 C9 C10 C1 178.4(2) . . . . ? F4 C9 C10 C5 -179.51(17) . . . . ? C8 C9 C10 C5 -0.2(3) . . . . ? C6 C5 C10 C1 -179.76(18) . . . . ? C4 C5 C10 C1 1.1(3) . . . . ? C6 C5 C10 C9 -1.1(3) . . . . ? C4 C5 C10 C9 179.73(19) . . . . ? C1 C2 C11 O1 154.4(2) . . . . ? C3 C2 C11 O1 -24.6(3) . . . . ? C1 C2 C11 N1 -25.0(3) . . . . ? C3 C2 C11 N1 156.10(19) . . . . ? _diffrn_measured_fraction_theta_max 0.947 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.947 _refine_diff_density_max 0.294 _refine_diff_density_min -0.294 _refine_diff_density_rms 0.067