# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 1999 # CCDC Number: 188/188 data_global _publ_contact_author 'Andrei S.Batsanov' _publ_contact_author_email a.s.batsanov@durham.ac.uk loop_ _publ_author_name 'Banks, John' 'Batsanov, Andrei S.' 'Howard, Judith A. K.' 'O'Hagan, David' 'Rzepa, Henry S.' 'Martin-Santamarina, Sonsoles' _journal_name_full 'Chemical Communications' _journal_volume '?' _journal_page_first '?' _journal_page_last '?' _journal_year '1999' _ccdc_journal_depnumber '?' _publ_section_title ; The preferred conformation of \a-fluoroamides. ; #============================================================ data_(1a) _audit_creation_method SHELXL _chemical_name_systematic ; N-fluoroacetyl-(S)-phenylalanine ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C11 H12 F N O3' _chemical_formula_weight 225.22 _chemical_melting_point ? _chemical_compound_source ? _ccdc_compound_id '1a' _ccdc_biological_activity '?' _ccdc_polymorph '?' _ccdc_disorder ; Phenyl ring, C(11) to C(16) with their hydrogens, is disordered over positions A and B, with equal occupancies. ; _ccdc_comments '?' 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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/2, y+1/2, -z' 'x+1/2, -y+1/2, -z' _cell_length_a 9.366(1) _cell_length_b 16.003(2) _cell_length_c 7.598(1) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1138.8(1) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 488 _cell_measurement_theta_min 12 _cell_measurement_theta_max 22 _exptl_crystal_description ? _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.34 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.314 _exptl_crystal_density_method ? _exptl_crystal_F_000 472 _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; Frames of 0.3\% \w, 10 s/frame. ; _diffrn_ambient_temperature 120(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 'SMART 1K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.2 _diffrn_reflns_number 8013 _diffrn_reflns_av_R_equivalents 0.0248 _diffrn_reflns_av_sigmaI/netI 0.0166 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.52 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2597 _reflns_number_observed 2497 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'SMART (Bruker, 1996)' _computing_cell_refinement 'SMART (Bruker, 1996)' _computing_data_reduction 'SAINT (Bruker, 1996)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'SHELXTL 5/VMS' _computing_publication_material 'SHELXTL 5/VMS' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 1 flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0380P)^2^+0.2364P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'from known configuration of the parent amino-acid' _refine_ls_abs_structure_Flack 0.96(69) _refine_ls_number_reflns 2596 _refine_ls_number_parameters 192 _refine_ls_number_restraints 57 _refine_ls_R_factor_all 0.0335 _refine_ls_R_factor_obs 0.0317 _refine_ls_wR_factor_all 0.0803 _refine_ls_wR_factor_obs 0.0784 _refine_ls_goodness_of_fit_all 1.097 _refine_ls_goodness_of_fit_obs 1.099 _refine_ls_restrained_S_all 1.100 _refine_ls_restrained_S_obs 1.097 _refine_ls_shift/esd_max -0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.65370(9) 0.25432(7) 0.68072(12) 0.0273(2) Uani 1 d . . H01 H 0.6298(22) 0.2359(14) 0.7906(32) 0.061(6) Uiso 1 d . . O2 O 0.44713(9) 0.19043(6) 0.61178(12) 0.0274(2) Uani 1 d . . O3 O 0.61149(10) 0.22398(6) 0.01670(11) 0.0288(2) Uani 1 d . . F F 0.30211(9) 0.10674(6) 0.11709(11) 0.0384(2) Uani 1 d . . N1 N 0.48669(11) 0.20849(6) 0.26932(13) 0.0196(2) Uani 1 d . . H1N H 0.4145(19) 0.1904(11) 0.3137(22) 0.029(4) Uiso 1 d . . C1 C 0.55473(12) 0.22759(8) 0.56989(15) 0.0202(2) Uani 1 d . . C2 C 0.59053(12) 0.25087(7) 0.38107(15) 0.0176(2) Uani 1 d . . H2 H 0.6891(15) 0.2296(9) 0.3570(18) 0.017(3) Uiso 1 d . . C3 C 0.59253(14) 0.34667(8) 0.3556(2) 0.0236(3) Uani 1 d D . H31 H 0.6212(17) 0.3557(11) 0.2308(25) 0.033(4) Uiso 1 d . . H32 H 0.6641(18) 0.3690(10) 0.4278(23) 0.029(4) Uiso 1 d . . C4 C 0.50633(12) 0.19693(8) 0.0979(2) 0.0202(2) Uani 1 d . . C5 C 0.39109(14) 0.14939(9) 0.0008(2) 0.0264(3) Uani 1 d . . H51 H 0.3337(19) 0.1915(11) -0.0651(24) 0.037(5) Uiso 1 d . . H52 H 0.4373(18) 0.1100(11) -0.0797(25) 0.037(4) Uiso 1 d . . C11A C 0.4575(4) 0.3883(4) 0.4240(5) 0.0249(9) Uani 0.50 d PD 1 C12A C 0.4304(4) 0.4057(2) 0.6017(5) 0.0314(6) Uani 0.50 d PD 1 H12A H 0.4984(4) 0.3897(2) 0.6880(5) 0.038 Uiso 0.50 d PR 1 C13A C 0.3051(4) 0.4462(2) 0.6545(6) 0.0442(7) Uani 0.50 d PD 1 H13A H 0.2897(4) 0.4572(2) 0.7759(6) 0.053 Uiso 0.50 d PR 1 C14A C 0.2028(4) 0.4707(2) 0.5324(7) 0.0504(9) Uani 0.50 d PD 1 H14A H 0.1186(4) 0.4990(2) 0.5689(7) 0.060 Uiso 0.50 d PR 1 C15A C 0.2268(4) 0.4527(3) 0.3542(8) 0.0487(8) Uani 0.50 d PD 1 H15A H 0.1576(4) 0.4681(3) 0.2688(8) 0.058 Uiso 0.50 d PR 1 C16A C 0.3498(4) 0.4129(2) 0.3024(5) 0.0336(6) Uani 0.50 d PD 1 H16A H 0.3635(4) 0.4014(2) 0.1810(5) 0.040 Uiso 0.50 d PR 1 C11B C 0.4483(4) 0.3900(4) 0.3641(5) 0.0249(9) Uani 0.50 d PD 2 C12B C 0.3939(4) 0.4103(2) 0.5244(5) 0.0314(6) Uani 0.50 d PD 2 H12B H 0.4447(4) 0.3963(2) 0.6286(5) 0.038 Uiso 0.50 d PR 2 C13B C 0.2611(4) 0.4523(2) 0.5349(6) 0.0442(7) Uani 0.50 d PD 2 H13B H 0.2208(4) 0.4669(2) 0.6454(6) 0.053 Uiso 0.50 d PR 2 C14B C 0.1924(4) 0.4713(2) 0.3808(8) 0.0504(9) Uani 0.50 d PD 2 H14B H 0.1027(4) 0.4989(2) 0.3868(8) 0.060 Uiso 0.50 d PR 2 C15B C 0.2469(4) 0.4524(2) 0.2194(6) 0.0487(8) Uani 0.50 d PD 2 H15B H 0.1968(4) 0.4672(2) 0.1153(6) 0.058 Uiso 0.50 d PR 2 C16B C 0.3770(4) 0.4113(2) 0.2099(5) 0.0336(6) Uani 0.50 d PD 2 H16B H 0.4172(4) 0.3977(2) 0.0987(5) 0.040 Uiso 0.50 d PR 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 O1 0.0224(4) 0.0445(6) 0.0150(4) 0.0016(4) -0.0023(3) -0.0075(4) O2 0.0216(4) 0.0430(5) 0.0175(4) 0.0037(4) 0.0008(3) -0.0068(4) O3 0.0223(4) 0.0488(6) 0.0153(4) -0.0021(4) 0.0009(3) -0.0082(4) F 0.0413(5) 0.0469(5) 0.0271(4) -0.0039(4) 0.0057(4) -0.0228(4) N1 0.0180(5) 0.0248(5) 0.0160(5) -0.0004(4) 0.0014(4) -0.0023(4) C1 0.0178(5) 0.0272(6) 0.0157(5) -0.0004(4) 0.0001(4) 0.0006(4) C2 0.0155(5) 0.0232(5) 0.0142(5) -0.0007(4) 0.0006(4) -0.0004(4) C3 0.0212(6) 0.0243(6) 0.0253(6) 0.0008(5) 0.0004(5) -0.0031(5) C4 0.0180(5) 0.0248(5) 0.0177(5) 0.0002(4) -0.0016(4) 0.0018(4) C5 0.0244(6) 0.0353(7) 0.0193(6) -0.0031(5) 0.0014(5) -0.0065(5) C11A 0.0201(7) 0.0177(6) 0.037(3) 0.000(2) -0.0099(14) -0.0021(6) C12A 0.032(2) 0.0243(8) 0.038(2) -0.0033(14) 0.0069(12) 0.0011(10) C13A 0.039(2) 0.0261(10) 0.068(2) -0.0071(14) 0.0180(14) 0.0016(10) C14A 0.0233(12) 0.0241(11) 0.104(2) -0.005(2) 0.010(2) 0.0030(9) C15A 0.0301(13) 0.0307(12) 0.085(2) 0.003(2) -0.009(2) 0.0034(10) C16A 0.0337(13) 0.0258(8) 0.041(2) 0.0054(13) -0.0089(13) -0.0030(8) C11B 0.0201(7) 0.0177(6) 0.037(3) 0.000(2) -0.0099(14) -0.0021(6) C12B 0.032(2) 0.0243(8) 0.038(2) -0.0033(14) 0.0069(12) 0.0011(10) C13B 0.039(2) 0.0261(10) 0.068(2) -0.0071(14) 0.0180(14) 0.0016(10) C14B 0.0233(12) 0.0241(11) 0.104(2) -0.005(2) 0.010(2) 0.0030(9) C15B 0.0301(13) 0.0307(12) 0.085(2) 0.003(2) -0.009(2) 0.0034(10) C16B 0.0337(13) 0.0258(8) 0.041(2) 0.0054(13) -0.0089(13) -0.0030(8) _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 H01 0.91(2) . ? O1 C1 1.3233(14) . ? O2 C1 1.2127(15) . ? O2 H1N 2.29(2) . ? O3 C4 1.2401(15) . ? F C5 1.3934(15) . ? F H1N 2.27(2) . ? N1 H1N 0.81(2) . ? N1 C4 1.328(2) . ? N1 C2 1.4584(15) . ? C1 C2 1.520(2) . ? C2 C3 1.545(2) . ? C3 C11B 1.520(2) . ? C3 C11A 1.521(2) . ? C4 C5 1.513(2) . ? C11A C12A 1.402(5) . ? C11A C16A 1.423(4) . ? C12A C13A 1.400(5) . ? C13A C14A 1.390(6) . ? C14A C15A 1.403(8) . ? C15A C16A 1.374(5) . ? C11B C12B 1.359(5) . ? C11B C16B 1.391(5) . ? C12B C13B 1.416(5) . ? C13B C14B 1.371(8) . ? C14B C15B 1.363(7) . ? C15B C16B 1.386(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 H01 O1 C1 107.8(14) . . ? C1 O2 H1N 81.4(5) . . ? C5 F H1N 81.4(5) . . ? H1N N1 C4 118.3(12) . . ? H1N N1 C2 118.8(12) . . ? C4 N1 C2 122.91(10) . . ? O2 C1 O1 125.00(11) . . ? O2 C1 C2 123.46(10) . . ? O1 C1 C2 111.53(10) . . ? N1 C2 C1 106.77(9) . . ? N1 C2 C3 113.35(10) . . ? C1 C2 C3 111.36(10) . . ? C11B C3 C2 115.9(3) . . ? C11A C3 C2 112.4(3) . . ? O3 C4 N1 123.31(11) . . ? O3 C4 C5 119.96(11) . . ? N1 C4 C5 116.72(11) . . ? F C5 C4 111.33(10) . . ? C12A C11A C16A 116.2(2) . . ? C12A C11A C3 124.5(3) . . ? C16A C11A C3 119.3(3) . . ? C13A C12A C11A 121.4(3) . . ? C14A C13A C12A 121.1(4) . . ? C13A C14A C15A 118.4(4) . . ? C16A C15A C14A 120.4(4) . . ? C15A C16A C11A 122.5(4) . . ? C12B C11B C16B 121.1(2) . . ? C12B C11B C3 118.7(3) . . ? C16B C11B C3 120.1(3) . . ? C11B C12B C13B 119.5(3) . . ? C14B C13B C12B 118.0(4) . . ? C15B C14B C13B 122.9(3) . . ? C14B C15B C16B 118.8(4) . . ? C15B C16B C11B 119.6(4) . . ? _refine_diff_density_max 0.187 _refine_diff_density_min -0.242 _refine_diff_density_rms 0.057 #=======================================================END data_(1b) _audit_creation_method SHELXL _chemical_name_systematic ; N-propionyl-(S)-phenylalanine ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C12 H15 N O3' _chemical_formula_weight 221.25 _chemical_melting_point ? _chemical_compound_source ? _ccdc_compound_id '1b' _ccdc_biological_activity '?' _ccdc_polymorph '?' _ccdc_disorder ; none ; _ccdc_comments '?' 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 5.754(2) _cell_length_b 8.139(2) _cell_length_c 24.873(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1164.9(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 24.0 _cell_measurement_theta_max 26.3 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.262 _exptl_crystal_density_method ? _exptl_crystal_F_000 472 _exptl_absorpt_coefficient_mu 0.746 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9404 _exptl_absorpt_correction_T_max 1.0000 _exptl_special_details ; T_max,min determined from \y-scans but no absorption correction applied. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Rigaku AFC6S 4-circle diffractometer' _diffrn_measurement_method '\w scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 2.4 _diffrn_reflns_number 1899 _diffrn_reflns_av_R_equivalents 0.0315 _diffrn_reflns_av_sigmaI/netI 0.0438 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 3.55 _diffrn_reflns_theta_max 75.00 _reflns_number_total 1615 _reflns_number_observed 1417 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'AFC/MSC' _computing_cell_refinement 'AFC/MSC' _computing_data_reduction teXsan _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement on F^2^ for ALL reflections except for 18 flagged by the user for potential systematic errors (beam obstruction by \x circle). Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0263P)^2^+0.3055P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0060(9) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.16(33) _refine_ls_number_reflns 1597 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0467 _refine_ls_R_factor_obs 0.0358 _refine_ls_wR_factor_all 0.1189 _refine_ls_wR_factor_obs 0.0786 _refine_ls_goodness_of_fit_all 1.065 _refine_ls_goodness_of_fit_obs 1.071 _refine_ls_restrained_S_all 1.529 _refine_ls_restrained_S_obs 1.071 _refine_ls_shift/esd_max -0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.4160(3) -0.0077(2) 0.27516(6) 0.0323(4) Uani 1 d . . H01 H 0.5138(69) -0.0584(42) 0.2445(14) 0.076(11) Uiso 1 d . . O2 O 0.7475(3) 0.0019(2) 0.32228(6) 0.0272(4) Uani 1 d . . O3 O 0.4116(3) 0.3644(2) 0.31073(6) 0.0263(4) Uani 1 d . . N1 N 0.1885(3) 0.1733(2) 0.34940(7) 0.0198(4) Uani 1 d . . H1 H 0.0562(46) 0.1244(30) 0.3521(9) 0.022(7) Uiso 1 d . . C1 C 0.5392(4) 0.0232(3) 0.31828(8) 0.0218(5) Uani 1 d . . C2 C 0.3930(4) 0.0807(3) 0.36568(8) 0.0207(5) Uani 1 d . . H2 H 0.4896(4) 0.1517(3) 0.38833(8) 0.023(6) Uiso 1 d R . C3 C 0.3210(4) -0.0693(3) 0.39896(8) 0.0246(5) Uani 1 d . . H31 H 0.2014(4) -0.1287(3) 0.37957(8) 0.032(7) Uiso 1 d R . H32 H 0.4540(4) -0.1417(3) 0.40254(8) 0.039(8) Uiso 1 d R . C4 C 0.2143(4) 0.3112(3) 0.32034(8) 0.0201(5) Uani 1 d . . C5 C -0.0005(4) 0.3975(3) 0.30140(9) 0.0255(5) Uani 1 d . . H51 H -0.1362(4) 0.3437(3) 0.31643(9) 0.033(7) Uiso 1 d R . H52 H -0.0103(4) 0.3899(3) 0.26254(9) 0.030(7) Uiso 1 d R . C6 C -0.0006(5) 0.5779(3) 0.31799(11) 0.0349(6) Uani 1 d . . H61 H -0.1395(40) 0.6316(35) 0.3067(9) 0.043(5) Uiso 1 d G . H62 H 0.1289(41) 0.6296(36) 0.3035(9) 0.043(5) Uiso 1 d G . H63 H 0.0054(43) 0.5889(34) 0.3571(9) 0.043(5) Uiso 1 d G . C11 C 0.2304(4) -0.0283(3) 0.45469(8) 0.0233(5) Uani 1 d . . C12 C 0.3679(5) 0.0606(3) 0.49057(9) 0.0295(6) Uani 1 d . . H12 H 0.5103(5) 0.1022(3) 0.47928(9) 0.038(8) Uiso 1 d R . C13 C 0.2947(5) 0.0872(3) 0.54277(9) 0.0359(7) Uani 1 d . . H13 H 0.3875(5) 0.1476(3) 0.56616(9) 0.041(8) Uiso 1 d R . C14 C 0.0854(5) 0.0254(3) 0.56044(9) 0.0375(7) Uani 1 d . . H14 H 0.0386(5) 0.0411(3) 0.59585(9) 0.053(9) Uiso 1 d R . C15 C -0.0537(5) -0.0603(3) 0.52503(10) 0.0359(6) Uani 1 d . . H15 H -0.1969(5) -0.1002(3) 0.53643(10) 0.042(8) Uiso 1 d R . C16 C 0.0187(4) -0.0873(3) 0.47238(9) 0.0285(5) Uani 1 d . . H16 H -0.0764(4) -0.1455(3) 0.44889(9) 0.031(7) Uiso 1 d 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 O1 0.0233(9) 0.0491(11) 0.0244(8) -0.0141(8) -0.0023(7) 0.0035(10) O2 0.0205(8) 0.0335(9) 0.0277(8) -0.0027(7) -0.0013(7) -0.0008(8) O3 0.0223(8) 0.0341(9) 0.0226(7) 0.0090(7) -0.0014(7) -0.0049(8) N1 0.0161(10) 0.0216(10) 0.0217(9) -0.0007(7) 0.0021(8) -0.0020(9) C1 0.0209(11) 0.0213(11) 0.0231(11) 0.0000(9) -0.0006(9) -0.0022(10) C2 0.0215(11) 0.0213(11) 0.0193(10) -0.0004(8) -0.0012(9) -0.0015(11) C3 0.0311(13) 0.0208(11) 0.0218(10) -0.0005(9) 0.0002(10) -0.0012(11) C4 0.0230(11) 0.0219(11) 0.0154(9) -0.0013(8) -0.0014(9) -0.0019(10) C5 0.0222(12) 0.0274(12) 0.0269(11) 0.0025(9) -0.0028(9) -0.0011(11) C6 0.036(2) 0.0290(13) 0.0400(14) 0.0007(12) -0.0016(13) 0.0015(13) C11 0.0289(12) 0.0189(11) 0.0221(10) 0.0034(8) 0.0012(10) 0.0026(11) C12 0.0314(13) 0.0306(12) 0.0266(11) 0.0044(10) 0.0002(10) -0.0038(12) C13 0.052(2) 0.0327(14) 0.0226(11) -0.0003(10) -0.0024(12) -0.0008(15) C14 0.057(2) 0.0297(13) 0.0260(12) 0.0043(11) 0.0138(13) 0.0101(14) C15 0.0369(15) 0.0306(13) 0.0402(14) 0.0116(12) 0.0139(13) 0.0062(13) C16 0.0297(13) 0.0245(12) 0.0312(12) 0.0031(10) -0.0009(11) -0.0017(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 O1 C1 1.310(3) . ? O1 H01 1.03(4) . ? O2 C1 1.215(3) . ? O3 C4 1.238(3) . ? N1 C4 1.343(3) . ? N1 C2 1.455(3) . ? N1 H1 0.86(3) . ? C1 C2 1.522(3) . ? C2 C3 1.532(3) . ? C2 H2 0.98 . ? C3 C11 1.518(3) . ? C3 H31 0.97 . ? C3 H32 0.97 . ? C4 C5 1.498(3) . ? C5 C6 1.525(4) . ? C5 H51 0.97 . ? C5 H52 0.97 . ? C6 H61 0.95(2) . ? C6 H62 0.93(2) . ? C6 H63 0.98(2) . ? C11 C16 1.381(3) . ? C11 C12 1.395(3) . ? C12 C13 1.382(3) . ? C12 H12 0.93 . ? C13 C14 1.377(4) . ? C13 H13 0.93 . ? C14 C15 1.380(4) . ? C14 H14 0.93 . ? C15 C16 1.392(3) . ? C15 H15 0.93 . ? C16 H16 0.93 . ? 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 H01 112.7(21) . . ? C4 N1 C2 119.6(2) . . ? C4 N1 H1 121.7(17) . . ? C2 N1 H1 116.9(17) . . ? O2 C1 O1 125.0(2) . . ? O2 C1 C2 121.7(2) . . ? O1 C1 C2 113.2(2) . . ? N1 C2 C1 113.0(2) . . ? N1 C2 C3 110.2(2) . . ? C1 C2 C3 108.9(2) . . ? N1 C2 H2 108.23(11) . . ? C1 C2 H2 108.26(12) . . ? C3 C2 H2 108.24(12) . . ? C11 C3 C2 114.3(2) . . ? C11 C3 H31 108.64(13) . . ? C2 C3 H31 108.71(12) . . ? C11 C3 H32 108.72(13) . . ? C2 C3 H32 108.68(13) . . ? H31 C3 H32 107.6 . . ? O3 C4 N1 119.8(2) . . ? O3 C4 C5 122.1(2) . . ? N1 C4 C5 118.0(2) . . ? C4 C5 C6 111.5(2) . . ? C4 C5 H51 109.34(13) . . ? C6 C5 H51 109.28(15) . . ? C4 C5 H52 109.32(12) . . ? C6 C5 H52 109.35(14) . . ? H51 C5 H52 108.0 . . ? C5 C6 H61 111.2(17) . . ? C5 C6 H62 109.4(18) . . ? H61 C6 H62 110.5(18) . . ? C5 C6 H63 110.9(17) . . ? H61 C6 H63 106.4(18) . . ? H62 C6 H63 108.4(19) . . ? C16 C11 C12 118.5(2) . . ? C16 C11 C3 121.2(2) . . ? C12 C11 C3 120.2(2) . . ? C13 C12 C11 120.6(2) . . ? C13 C12 H12 119.7(2) . . ? C11 C12 H12 119.71(14) . . ? C14 C13 C12 120.6(2) . . ? C14 C13 H13 119.69(15) . . ? C12 C13 H13 119.7(2) . . ? C13 C14 C15 119.2(2) . . ? C13 C14 H14 120.38(15) . . ? C15 C14 H14 120.4(2) . . ? C14 C15 C16 120.5(3) . . ? C14 C15 H15 119.7(2) . . ? C16 C15 H15 119.8(2) . . ? C11 C16 C15 120.6(2) . . ? C11 C16 H16 119.72(14) . . ? C15 C16 H16 119.7(2) . . ? _refine_diff_density_max 0.153 _refine_diff_density_min -0.147 _refine_diff_density_rms 0.037 #====================================================END data_(2) _audit_creation_method SHELXL _chemical_name_systematic ; N-phenyl-2-(S)-fluoropropionamide with ca. 10% of N-phenyl-2-(R)-fluoropropionamide ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C9 H10 F N O' _chemical_formula_weight 167.18 _chemical_melting_point ? _chemical_compound_source ? _ccdc_compound_id '2' _ccdc_biological_activity '?' _ccdc_polymorph '?' _ccdc_disorder ; 2 molecules in the unit cell: molecule A a superposition of 79(1)% of (S)-isomer and 21(1)% of (R)-isomer, molecule B is (S)-isomer only. Thus in A, C(18) and C(19) with their hydrogens are disordered over 2 positions, the major one of (S)-2 and the minor one [C(18') and C(19')] of (R)-2. ; _ccdc_comments '?' 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 P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 5.367(1) _cell_length_b 8.821(4) _cell_length_c 9.893(3) _cell_angle_alpha 106.65(2) _cell_angle_beta 101.84(2) _cell_angle_gamma 105.13(2) _cell_volume 412.8(2) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 22 _cell_measurement_theta_min 24.0 _cell_measurement_theta_max 36.3 _exptl_crystal_description fragment _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.345 _exptl_crystal_density_method ? _exptl_crystal_F_000 176 _exptl_absorpt_coefficient_mu 0.867 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Rigaku AFC6S 4-circle diffractometer' _diffrn_measurement_method '2\q/\w scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.7 _diffrn_reflns_number 1593 _diffrn_reflns_av_R_equivalents 0.0155 _diffrn_reflns_av_sigmaI/netI 0.0242 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 4.90 _diffrn_reflns_theta_max 74.96 _reflns_number_total 1592 _reflns_number_observed 1482 _reflns_observed_criterion >2sigma(I) _computing_data_collection AFC/MSC _computing_cell_refinement AFC/MSC _computing_data_reduction TEXSAN _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement on F^2^ for ALL reflections except for 10 flagged by the user for potential systematic errors. Weighted R- factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0848P)^2^+0.0268P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.0(2) _refine_ls_number_reflns 1582 _refine_ls_number_parameters 236 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0492 _refine_ls_R_factor_obs 0.0431 _refine_ls_wR_factor_all 0.1536 _refine_ls_wR_factor_obs 0.1122 _refine_ls_goodness_of_fit_all 1.092 _refine_ls_goodness_of_fit_obs 1.098 _refine_ls_restrained_S_all 1.441 _refine_ls_restrained_S_obs 1.097 _refine_ls_shift/esd_max 0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group F1 F 0.5391(4) 0.6587(3) 0.7242(2) 0.0534(7) Uani 1 d . . N1 N 0.2309(5) 0.4023(3) 0.4863(3) 0.0263(5) Uani 1 d . . H1 H 0.3982(87) 0.4317(48) 0.5293(42) 0.024(9) Uiso 1 d . . O1 O -0.1529(5) 0.4391(3) 0.5333(3) 0.0400(6) Uani 1 d . . C11 C 0.1118(6) 0.2612(3) 0.3513(3) 0.0245(6) Uani 1 d . . C12 C -0.1265(7) 0.2391(4) 0.2488(3) 0.0275(6) Uani 1 d . . H12 H -0.2160(7) 0.3193(4) 0.2656(3) 0.033 Uiso 1 d R . C13 C -0.2323(7) 0.0982(4) 0.1193(3) 0.0311(7) Uani 1 d . . H13 H -0.3954(7) 0.0824(4) 0.0487(3) 0.037 Uiso 1 d R . C14 C -0.1046(7) -0.0203(4) 0.0912(4) 0.0332(7) Uani 1 d . . H14 H -0.1807(7) -0.1170(4) 0.0028(4) 0.040 Uiso 1 d R . C15 C 0.1351(7) 0.0040(4) 0.1942(4) 0.0347(7) Uani 1 d . . H15 H 0.2258(7) -0.0755(4) 0.1765(4) 0.042 Uiso 1 d R . C16 C 0.2443(6) 0.1453(4) 0.3232(4) 0.0295(6) Uani 1 d . . H16 H 0.4103(6) 0.1638(4) 0.3928(4) 0.035 Uiso 1 d R . C17 C 0.0928(6) 0.4738(4) 0.5691(3) 0.0330(8) Uani 1 d . . C18 C 0.2658(8) 0.5968(5) 0.7264(4) 0.0278(12) Uani 0.793(12) d P 1 H18 H 0.2595(8) 0.5349(5) 0.7966(4) 0.036 Uiso 0.793(12) d PR 1 C19 C 0.1829(9) 0.7454(6) 0.7781(5) 0.0415(15) Uani 0.793(12) d P 1 H191 H -0.0054(9) 0.7069(6) 0.7786(5) 0.033(7) Uiso 0.793(12) d PR 1 H192 H 0.1989(9) 0.8121(6) 0.7144(5) 0.033(7) Uiso 0.793(12) d PR 1 H193 H 0.3004(9) 0.8148(6) 0.8791(5) 0.033(7) Uiso 0.793(12) d PR 1 C18' C 0.2519(39) 0.6656(24) 0.6813(21) 0.037(5) Uiso 0.207(12) d P 2 H18' H 0.2246(39) 0.7590(24) 0.6486(21) 0.048 Uiso 0.207(12) calc PR 2 C19' C 0.1997(38) 0.6580(22) 0.8203(19) 0.036(5) Uiso 0.207(12) d P 2 H194 H 0.2880(38) 0.7695(22) 0.8984(19) 0.053 Uiso 0.207(12) calc PR 2 H195 H 0.2723(38) 0.5771(22) 0.8493(19) 0.053 Uiso 0.207(12) calc PR 2 H196 H 0.0041(38) 0.6223(22) 0.8055(19) 0.053 Uiso 0.207(12) calc PR 2 F2 F 0.9911(4) 0.7956(3) 0.4431(2) 0.0394(5) Uani 1 d . . N2 N 0.6869(6) 0.5729(3) 0.1864(3) 0.0277(6) Uani 1 d . . H2 H 0.8445(90) 0.6052(50) 0.2148(43) 0.027(10) Uiso 1 d . . O2 O 0.3041(5) 0.6178(3) 0.2268(3) 0.0431(6) Uani 1 d . . C21 C 0.5717(6) 0.4475(4) 0.0426(3) 0.0275(6) Uani 1 d . . C22 C 0.3156(6) 0.3259(4) 0.0011(4) 0.0309(7) Uani 1 d . . H22 H 0.2125(6) 0.3284(4) 0.0686(4) 0.037 Uiso 1 d R . C23 C 0.2154(7) 0.2015(4) -0.1382(4) 0.0346(7) Uani 1 d . . H23 H 0.0407(7) 0.1197(4) -0.1664(4) 0.042 Uiso 1 d R . C24 C 0.3662(7) 0.1959(5) -0.2373(4) 0.0365(7) Uani 1 d . . H24 H 0.2951(7) 0.1100(5) -0.3327(4) 0.044 Uiso 1 d R . C25 C 0.6194(7) 0.3155(5) -0.1955(4) 0.0364(7) Uani 1 d . . H25 H 0.7229(7) 0.3132(5) -0.2628(4) 0.044 Uiso 1 d R . C26 C 0.7236(6) 0.4408(4) -0.0551(3) 0.0314(7) Uani 1 d . . H26 H 0.9003(6) 0.5210(4) -0.0256(3) 0.038 Uiso 1 d R . C27 C 0.5475(6) 0.6458(4) 0.2681(3) 0.0302(7) Uani 1 d . . C28 C 0.7116(7) 0.7654(4) 0.4254(3) 0.0321(7) Uani 1 d . . H28 H 0.6576(7) 0.7120(4) 0.4963(3) 0.042 Uiso 1 d R . C29 C 0.6647(8) 0.9301(4) 0.4606(4) 0.0416(8) Uani 1 d . . H291 H 0.7648(8) 1.0005(4) 0.5642(4) 0.043(6) Uiso 1 d R . H292 H 0.4712(8) 0.9121(4) 0.4442(4) 0.043(6) Uiso 1 d R . H293 H 0.7299(8) 0.9865(4) 0.3960(4) 0.043(6) Uiso 1 d 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 0.0159(11) 0.0645(15) 0.0477(11) -0.0153(11) 0.0040(9) 0.0061(10) N1 0.0149(15) 0.0329(13) 0.0263(12) 0.0062(11) 0.0032(11) 0.0078(10) O1 0.0189(13) 0.0501(14) 0.0377(12) -0.0004(11) 0.0078(9) 0.0094(10) C11 0.018(2) 0.0267(14) 0.0275(14) 0.0077(12) 0.0068(12) 0.0086(12) C12 0.023(2) 0.0300(14) 0.0304(14) 0.0098(12) 0.0070(12) 0.0124(12) C13 0.025(2) 0.034(2) 0.0286(15) 0.0069(12) 0.0034(13) 0.0101(13) C14 0.027(2) 0.0306(14) 0.0315(14) 0.0002(12) 0.0057(13) 0.0072(13) C15 0.025(2) 0.0325(15) 0.044(2) 0.0062(14) 0.0108(15) 0.0139(13) C16 0.016(2) 0.0339(14) 0.035(2) 0.0082(12) 0.0030(12) 0.0107(11) C17 0.021(2) 0.037(2) 0.029(2) -0.0011(13) 0.0063(14) 0.0072(13) C18 0.013(2) 0.035(2) 0.025(2) 0.002(2) 0.0008(14) 0.0054(15) C19 0.023(3) 0.039(2) 0.046(3) -0.008(2) 0.003(2) 0.015(2) F2 0.0195(10) 0.0492(11) 0.0383(10) 0.0029(9) 0.0005(8) 0.0148(8) N2 0.0143(15) 0.0324(12) 0.0323(13) 0.0072(11) 0.0028(11) 0.0096(10) O2 0.0214(13) 0.0458(14) 0.0469(14) -0.0022(11) 0.0026(11) 0.0144(10) C21 0.023(2) 0.0314(14) 0.0282(14) 0.0114(12) 0.0042(12) 0.0119(12) C22 0.022(2) 0.0352(15) 0.035(2) 0.0118(13) 0.0094(14) 0.0090(12) C23 0.025(2) 0.036(2) 0.035(2) 0.0085(14) 0.0050(14) 0.0064(13) C24 0.031(2) 0.041(2) 0.0301(15) 0.0054(13) 0.0039(14) 0.0122(14) C25 0.028(2) 0.049(2) 0.032(2) 0.0123(14) 0.0095(14) 0.0146(14) C26 0.022(2) 0.039(2) 0.033(2) 0.0120(13) 0.0068(13) 0.0109(12) C27 0.022(2) 0.0327(15) 0.033(2) 0.0068(12) 0.0056(13) 0.0126(12) C28 0.021(2) 0.034(2) 0.036(2) 0.0083(13) 0.0055(13) 0.0085(13) C29 0.030(2) 0.036(2) 0.047(2) 0.0001(15) 0.007(2) 0.0127(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 C18 1.433(4) . ? F1 C18' 1.54(2) . ? N1 H1 0.84(4) . ? N1 C17 1.348(4) . ? N1 C11 1.422(4) . ? O1 C17 1.222(4) . ? C11 C16 1.387(4) . ? C11 C12 1.388(5) . ? C12 C13 1.389(4) . ? C13 C14 1.388(5) . ? C14 C15 1.390(5) . ? C15 C16 1.388(4) . ? C17 C18 1.541(5) . ? C17 C18' 1.61(2) . ? C18 C19 1.480(6) . ? C18' C19' 1.47(3) . ? F2 C28 1.418(4) . ? N2 H2 0.78(4) . ? N2 C27 1.352(4) . ? N2 C21 1.418(4) . ? O2 C27 1.220(4) . ? C21 C26 1.385(4) . ? C21 C22 1.398(5) . ? C22 C23 1.383(4) . ? C23 C24 1.392(5) . ? C24 C25 1.379(5) . ? C25 C26 1.394(4) . ? C27 C28 1.524(4) . ? C28 C29 1.494(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 H1 N1 C17 114.7(26) . . ? H1 N1 C11 118.7(26) . . ? C17 N1 C11 125.1(3) . . ? C16 C11 C12 120.3(3) . . ? C16 C11 N1 117.7(3) . . ? C12 C11 N1 122.0(3) . . ? C11 C12 C13 119.1(3) . . ? C14 C13 C12 121.2(3) . . ? C13 C14 C15 119.1(3) . . ? C16 C15 C14 120.2(3) . . ? C11 C16 C15 120.1(3) . . ? O1 C17 N1 125.5(3) . . ? O1 C17 C18 119.4(3) . . ? N1 C17 C18 114.8(3) . . ? O1 C17 C18' 112.5(7) . . ? N1 C17 C18' 116.1(7) . . ? F1 C18 C19 106.9(3) . . ? F1 C18 C17 107.7(3) . . ? C19 C18 C17 113.6(4) . . ? C19' C18' F1 95.0(14) . . ? C19' C18' C17 101.9(13) . . ? F1 C18' C17 99.4(11) . . ? H2 N2 C27 119.9(30) . . ? H2 N2 C21 114.6(30) . . ? C27 N2 C21 125.3(3) . . ? C26 C21 C22 119.7(3) . . ? C26 C21 N2 118.8(3) . . ? C22 C21 N2 121.3(3) . . ? C23 C22 C21 119.5(3) . . ? C22 C23 C24 120.9(3) . . ? C25 C24 C23 119.5(3) . . ? C24 C25 C26 120.3(3) . . ? C21 C26 C25 120.2(3) . . ? O2 C27 N2 125.0(3) . . ? O2 C27 C28 119.1(3) . . ? N2 C27 C28 115.8(3) . . ? F2 C28 C29 108.7(3) . . ? F2 C28 C27 109.4(2) . . ? C29 C28 C27 112.0(3) . . ? 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 C16 C11 N1 C17 -143.3(3) . . . . ? C11 N1 C17 C18 166.3(3) . . . . ? N1 C17 C18 F1 24.5(5) . . . . ? C26 C21 N2 C27 149.0(3) . . . . ? C21 N2 C27 C28 174.4(3) . . . . ? N2 C27 C28 F2 9.9(4) . . . . ? _refine_diff_density_max 0.217 _refine_diff_density_min -0.290 _refine_diff_density_rms 0.051 #========================================================END