# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2004 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Douglas Young' 'Jean-Damien Charrier' 'David S. Hadfield' 'Peter B. Hitchcock' _publ_contact_author_name 'Prof Douglas Young' _publ_contact_author_address ; Department of Chemistry University of Sussex University of Sussex Falmer, Brighton Brighton Eat Sussex UNITED KINGDOM ; _publ_contact_author_email D.W.YOUNG@SUSSEX.AC.UK _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; Synthesis of (2S, 4S)- and (2S, 4R)- 5-Fluoroleucine and (2S, 4S)-[5, 5-2H2]-5-Fluoroleucine ; _publ_requested_category FO data_(1a)-apr2500 _database_code_depnum_ccdc_archive 'CCDC 224897' _audit_creation_date 2000-04-26T11:33:25-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.1beta5 _audit_conform_dict_location ftp://ftp.iucr.org/cifdics/cif_core_2.1beta5.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C6 H12 F1 N1 O2' _chemical_formula_structural 'C6 H12 F N O2' _chemical_formula_sum 'C6 H12 F N O2' _chemical_formula_weight 149.17 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2 _symmetry_space_group_name_Hall 'C 2y' _symmetry_Int_Tables_number 5 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 9.6878(16) _cell_length_b 5.3021(6) _cell_length_c 15.229(3) _cell_angle_alpha 90 _cell_angle_beta 107.292(5) _cell_angle_gamma 90 _cell_volume 746.89(19) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 19825 _cell_measurement_theta_min 3.705 _cell_measurement_theta_max 25.028 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.01 _exptl_crystal_density_diffrn 1.33 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 320 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION NOT APPLIED # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.11 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_measurement_device KappaCCD _diffrn_measurement_method CCD _diffrn_reflns_number 4317 _diffrn_reflns_av_R_equivalents 0.0566 _diffrn_reflns_av_sigmaI/netI 0.0602 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 4.2 _diffrn_reflns_theta_max 25.06 _diffrn_reflns_theta_full 25.06 _diffrn_measured_fraction_theta_full 0.984 _diffrn_measured_fraction_theta_max 0.984 _reflns_number_total 1290 _reflns_number_gt 1089 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; The F atom is disordered over 2 positions. There should be another H atom but it was not clear from a difference map whether it was in a NH3+ group or a CO2H group so it was omitted. 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^)+(0.1100P)^2^+0.2496P] 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_number_reflns 1290 _refine_ls_number_parameters 105 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0804 _refine_ls_R_factor_gt 0.0669 _refine_ls_wR_factor_ref 0.1826 _refine_ls_wR_factor_gt 0.1735 _refine_ls_goodness_of_fit_ref 1.102 _refine_ls_restrained_S_all 1.102 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(3) _refine_diff_density_max 0.24 _refine_diff_density_min -0.233 _refine_diff_density_rms 0.057 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.0327(3) -0.0067(4) 0.1283(2) 0.0608(9) Uani 1 1 d . . . O2 O -0.0691(2) 0.3650(4) 0.09079(16) 0.0437(7) Uani 1 1 d . . . N N 0.1790(4) 0.5797(6) 0.0830(2) 0.0441(8) Uani 1 1 d . . . H1B H 0.254(5) 0.623(9) 0.093(3) 0.051(13) Uiso 1 1 d . . . H1A H 0.144(4) 0.546(7) 0.016(3) 0.046(10) Uiso 1 1 d . . . C1 C 0.0395(4) 0.2225(6) 0.1168(2) 0.0383(8) Uani 1 1 d . . . C2 C 0.1881(3) 0.3496(7) 0.1411(3) 0.0440(9) Uani 1 1 d . . . H2 H 0.2598 0.2296 0.1287 0.053 Uiso 1 1 calc R . . C3 C 0.2406(5) 0.4332(8) 0.2416(3) 0.0575(11) Uani 1 1 d . B . H3A H 0.33 0.5333 0.2506 0.069 Uiso 1 1 calc R . . H3B H 0.1667 0.5472 0.2529 0.069 Uiso 1 1 calc R . . C4 C 0.2713(6) 0.2293(11) 0.3135(3) 0.0765(14) Uani 1 1 d . . . H4 H 0.187 0.1112 0.2991 0.092 Uiso 1 1 calc R A 1 C6 C 0.2892(11) 0.352(2) 0.4106(5) 0.166(5) Uani 1 1 d . B . H6A H 0.2014 0.4456 0.409 0.249 Uiso 1 1 calc R . . H6B H 0.3721 0.467 0.4258 0.249 Uiso 1 1 calc R . . H6C H 0.3054 0.2188 0.4572 0.249 Uiso 1 1 calc R . . C5 C 0.4012(9) 0.0855(17) 0.3142(5) 0.113(2) Uani 0.564(15) 1 d P B 1 H5A1 H 0.3875 0.0062 0.2533 0.136 Uiso 0.564(15) 1 calc PR B 1 H5A2 H 0.4854 0.2002 0.3266 0.136 Uiso 0.564(15) 1 calc PR B 1 F F 0.4267(16) -0.101(3) 0.3822(9) 0.204(7) Uani 0.564(15) 1 d P B 1 C5A C 0.4012(9) 0.0855(17) 0.3142(5) 0.113(2) Uani 0.436(15) 1 d P B 2 H5A H 0.4134 -0.0617 0.3558 0.136 Uiso 0.436(15) 1 calc PR B 2 H5B H 0.3949 0.025 0.2516 0.136 Uiso 0.436(15) 1 calc PR B 2 F1A F 0.5212(11) 0.2624(18) 0.3472(6) 0.112(4) Uiso 0.436(15) 1 d P B 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 0.0488(17) 0.0423(18) 0.095(2) 0.0080(14) 0.0278(15) -0.0021(11) O2 0.0292(12) 0.0487(15) 0.0533(14) 0.0090(11) 0.0122(10) -0.0024(10) N 0.0308(15) 0.0516(18) 0.0515(19) -0.0050(14) 0.0148(13) -0.0150(13) C1 0.0348(19) 0.040(2) 0.0430(18) -0.0021(15) 0.0163(14) -0.0031(15) C2 0.0276(15) 0.053(2) 0.052(2) 0.0003(17) 0.0136(14) 0.0003(15) C3 0.047(2) 0.069(3) 0.054(2) -0.0019(18) 0.0107(18) 0.0013(18) C4 0.064(3) 0.102(3) 0.053(3) 0.016(3) 0.003(2) -0.013(3) C6 0.168(8) 0.261(13) 0.067(4) 0.043(6) 0.030(5) 0.105(9) C5 0.135(6) 0.095(4) 0.097(5) 0.010(4) 0.015(4) 0.027(5) F 0.234(13) 0.180(12) 0.182(11) 0.059(8) 0.039(9) 0.064(10) C5A 0.135(6) 0.095(4) 0.097(5) 0.010(4) 0.015(4) 0.027(5) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 1.232(4) . ? O2 C1 1.259(4) . ? N C2 1.494(5) . ? C1 C2 1.533(5) . ? C2 C3 1.529(6) . ? C3 C4 1.503(6) . ? C4 C5 1.468(10) . ? C4 C6 1.577(10) . ? C5 F 1.400(14) . ? 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 O1 C1 O2 124.2(3) . . ? O1 C1 C2 119.0(3) . . ? O2 C1 C2 116.7(3) . . ? N C2 C3 107.5(3) . . ? N C2 C1 109.3(3) . . ? C3 C2 C1 112.2(3) . . ? C4 C3 C2 117.1(4) . . ? C5 C4 C3 111.3(5) . . ? C5 C4 C6 110.6(5) . . ? C3 C4 C6 109.2(6) . . ? F C5 C4 109.6(8) . . ? #===END data_(19)-jan399 _database_code_depnum_ccdc_archive 'CCDC 224898' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H36 N2 O5' _chemical_formula_weight 420.54 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' _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+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 9.005(2) _cell_length_b 16.541(5) _cell_length_c 16.841(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2508.5(11) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 7 _cell_measurement_theta_max 10 _exptl_crystal_description block _exptl_crystal_colour ? _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.114 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 912 _exptl_absorpt_coefficient_mu 0.078 _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 293(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 'Nonius CAD4' _diffrn_measurement_method \w--2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 0 _diffrn_reflns_number 6576 _diffrn_reflns_av_R_equivalents 0.0344 _diffrn_reflns_av_sigmaI/netI 0.0976 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 27.97 _reflns_number_total 6028 _reflns_number_gt 2531 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Enraf-Nonius CAD4' _computing_cell_refinement 'Enraf-Nonius CAD4' _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material SHELXL-93 _refine_special_details ; Hydrogen atoms on N1 and N2 were freely refined; other hydrogen atoms were in riding mode. The absolute structure was assigned on the basis of the known stereochemistry at C7. 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^)+(0.0565P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1.5(18) _refine_ls_number_reflns 6028 _refine_ls_number_parameters 279 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1789 _refine_ls_R_factor_gt 0.0672 _refine_ls_wR_factor_ref 0.1668 _refine_ls_wR_factor_gt 0.1267 _refine_ls_goodness_of_fit_ref 0.982 _refine_ls_restrained_S_all 0.982 _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 O1 O 0.1499(2) 0.24454(17) 0.45580(16) 0.0883(9) Uani 1 1 d . . . O2 O 0.2641(2) 0.28456(16) 0.17273(13) 0.0709(7) Uani 1 1 d . . . O3 O 0.5069(3) 0.2647(2) 0.14957(17) 0.1158(12) Uani 1 1 d . . . O4 O 0.7730(2) 0.16718(14) 0.29100(15) 0.0720(7) Uani 1 1 d . . . O5 O 0.5545(3) 0.10736(18) 0.26054(19) 0.1034(11) Uani 1 1 d . . . N1 N 0.3662(4) 0.1804(2) 0.46472(19) 0.0680(9) Uani 1 1 d . . . H1N H 0.455(4) 0.190(2) 0.471(2) 0.074(12) Uiso 1 1 d . . . N2 N 0.5651(3) 0.2350(2) 0.30579(18) 0.0636(8) Uani 1 1 d . . . H2N H 0.622(4) 0.2747(17) 0.3128(17) 0.051(10) Uiso 1 1 d . . . C1 C 0.2915(4) 0.0930(2) 0.5768(2) 0.0644(10) Uani 1 1 d . . . C2 C 0.1979(5) 0.0345(3) 0.6080(3) 0.0979(15) Uani 1 1 d . . . H2 H 0.1424 0.0023 0.5738 0.117 Uiso 1 1 calc R . . C3 C 0.1858(6) 0.0232(3) 0.6901(4) 0.115(2) Uani 1 1 d . . . H3 H 0.1245 -0.0169 0.7109 0.138 Uiso 1 1 calc R . . C4 C 0.2655(7) 0.0719(4) 0.7386(4) 0.1145(19) Uani 1 1 d . . . H4 H 0.2569 0.0654 0.7933 0.137 Uiso 1 1 calc R . . C5 C 0.3568(5) 0.1292(3) 0.7102(3) 0.0901(13) Uani 1 1 d . . . H5 H 0.4108 0.1613 0.7452 0.108 Uiso 1 1 calc R . . C6 C 0.3706(4) 0.1407(2) 0.6298(3) 0.0716(10) Uani 1 1 d . . . H6 H 0.4336 0.1808 0.6107 0.086 Uiso 1 1 calc R . . C7 C 0.3060(4) 0.1025(2) 0.4879(2) 0.0716(11) Uani 1 1 d . . . H7 H 0.2060 0.0985 0.4653 0.086 Uiso 1 1 calc R . . C8 C 0.3993(5) 0.0350(3) 0.4511(3) 0.1052(14) Uani 1 1 d . . . H8C H 0.3540 -0.0163 0.4621 0.158 Uiso 1 1 calc R . . H8B H 0.4975 0.0361 0.4733 0.158 Uiso 1 1 calc R . . H8A H 0.4052 0.0427 0.3947 0.158 Uiso 1 1 calc R . . C9 C 0.2853(4) 0.2461(2) 0.44981(18) 0.0566(8) Uani 1 1 d . . . C10 C 0.3680(4) 0.3197(2) 0.42143(19) 0.0608(9) Uani 1 1 d . . . H10 H 0.4730 0.3139 0.4357 0.073 Uiso 1 1 calc R . . C11 C 0.3074(5) 0.3952(2) 0.4604(3) 0.0908(12) Uani 1 1 d . . . H11C H 0.3176 0.3907 0.5170 0.136 Uiso 1 1 calc R . . H11B H 0.2044 0.4013 0.4471 0.136 Uiso 1 1 calc R . . H11A H 0.3618 0.4414 0.4420 0.136 Uiso 1 1 calc R . . C12 C 0.3557(4) 0.3268(2) 0.33031(19) 0.0620(9) Uani 1 1 d . . . H12B H 0.2521 0.3352 0.3167 0.074 Uiso 1 1 calc R . . H12A H 0.4099 0.3746 0.3136 0.074 Uiso 1 1 calc R . . C13 C 0.4129(3) 0.2550(2) 0.28345(17) 0.0591(9) Uani 1 1 d . . . H13 H 0.3502 0.2084 0.2963 0.071 Uiso 1 1 calc R . . C14 C 0.4043(4) 0.2686(2) 0.1944(2) 0.0742(11) Uani 1 1 d . . . C15 C 0.2242(5) 0.2924(3) 0.0884(2) 0.0780(11) Uani 1 1 d . . . C16 C 0.3152(5) 0.3574(3) 0.0479(2) 0.1122(17) Uani 1 1 d . . . H16C H 0.2837 0.3628 -0.0063 0.168 Uiso 1 1 calc R . . H16B H 0.4184 0.3428 0.0494 0.168 Uiso 1 1 calc R . . H16A H 0.3014 0.4079 0.0751 0.168 Uiso 1 1 calc R . . C17 C 0.2378(6) 0.2106(3) 0.0498(3) 0.1176(17) Uani 1 1 d . . . H17C H 0.1974 0.2128 -0.0029 0.176 Uiso 1 1 calc R . . H17B H 0.1841 0.1714 0.0805 0.176 Uiso 1 1 calc R . . H17A H 0.3405 0.1954 0.0472 0.176 Uiso 1 1 calc R . . C18 C 0.0618(5) 0.3180(3) 0.0932(2) 0.1048(16) Uani 1 1 d . . . H18C H 0.0072 0.2791 0.1238 0.157 Uiso 1 1 calc R . . H18B H 0.0209 0.3210 0.0406 0.157 Uiso 1 1 calc R . . H18A H 0.0550 0.3701 0.1182 0.157 Uiso 1 1 calc R . . C19 C 0.6242(4) 0.1646(3) 0.2824(2) 0.0684(10) Uani 1 1 d . . . C20 C 0.8684(4) 0.1014(2) 0.2622(2) 0.0693(10) Uani 1 1 d . . . C21 C 1.0220(5) 0.1345(3) 0.2817(3) 0.1030(15) Uani 1 1 d . . . H21C H 1.0359 0.1854 0.2553 0.155 Uiso 1 1 calc R . . H21B H 1.0963 0.0970 0.2640 0.155 Uiso 1 1 calc R . . H21A H 1.0307 0.1420 0.3380 0.155 Uiso 1 1 calc R . . C22 C 0.8345(6) 0.0251(3) 0.3058(3) 0.1141(17) Uani 1 1 d . . . H22C H 0.9009 -0.0168 0.2885 0.171 Uiso 1 1 calc R . . H22B H 0.7339 0.0091 0.2952 0.171 Uiso 1 1 calc R . . H22A H 0.8469 0.0337 0.3618 0.171 Uiso 1 1 calc R . . C23 C 0.8478(5) 0.0913(3) 0.1745(2) 0.1108(16) Uani 1 1 d . . . H23C H 0.7472 0.0757 0.1637 0.166 Uiso 1 1 calc R . . H23B H 0.9142 0.0503 0.1553 0.166 Uiso 1 1 calc R . . H23A H 0.8690 0.1415 0.1482 0.166 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 O1 0.0407(13) 0.104(2) 0.120(2) 0.0290(19) 0.0039(14) 0.0039(15) O2 0.0528(15) 0.109(2) 0.0508(14) 0.0003(13) 0.0049(11) -0.0043(13) O3 0.0642(17) 0.198(4) 0.085(2) 0.013(2) 0.0247(15) 0.003(2) O4 0.0458(14) 0.0676(16) 0.1026(19) -0.0169(15) -0.0073(13) 0.0049(13) O5 0.0691(19) 0.086(2) 0.155(3) -0.043(2) 0.0034(18) -0.0272(17) N1 0.0395(17) 0.081(2) 0.084(2) 0.0228(18) -0.0061(17) -0.0055(18) N2 0.0405(16) 0.062(2) 0.088(2) -0.0079(18) -0.0049(15) -0.0079(17) C1 0.0412(18) 0.059(2) 0.093(3) 0.026(2) 0.005(2) 0.008(2) C2 0.060(2) 0.076(3) 0.158(5) 0.045(3) 0.002(3) -0.003(2) C3 0.074(3) 0.098(4) 0.171(6) 0.081(4) 0.030(4) 0.010(3) C4 0.101(4) 0.120(5) 0.123(4) 0.057(4) 0.026(4) 0.036(4) C5 0.102(4) 0.089(3) 0.080(3) 0.023(2) 0.006(3) 0.024(3) C6 0.057(2) 0.072(2) 0.087(3) 0.017(2) 0.001(2) 0.006(2) C7 0.057(2) 0.068(2) 0.089(3) 0.010(2) -0.012(2) -0.008(2) C8 0.123(4) 0.087(3) 0.106(3) -0.014(3) 0.002(3) -0.010(3) C9 0.0447(18) 0.075(2) 0.0499(19) 0.0073(18) -0.0034(17) 0.002(2) C10 0.0480(19) 0.075(2) 0.059(2) 0.0070(19) -0.0050(17) -0.001(2) C11 0.103(3) 0.087(3) 0.083(3) -0.008(2) 0.001(3) 0.005(3) C12 0.0444(18) 0.079(2) 0.062(2) 0.0177(19) 0.0009(17) 0.0019(19) C13 0.0396(17) 0.079(2) 0.058(2) 0.004(2) 0.0018(16) -0.0076(18) C14 0.051(2) 0.107(3) 0.064(2) 0.000(2) 0.007(2) -0.007(2) C15 0.076(3) 0.111(3) 0.047(2) -0.004(2) 0.001(2) -0.001(3) C16 0.127(4) 0.139(4) 0.071(3) 0.024(3) 0.017(3) -0.012(3) C17 0.129(4) 0.138(4) 0.086(3) -0.037(3) -0.001(3) -0.003(4) C18 0.088(3) 0.155(4) 0.072(3) -0.007(3) -0.024(2) 0.017(3) C19 0.059(2) 0.066(3) 0.080(3) -0.011(2) 0.001(2) -0.007(2) C20 0.073(3) 0.067(2) 0.069(3) -0.008(2) 0.007(2) 0.013(2) C21 0.063(3) 0.111(4) 0.135(4) -0.027(3) -0.012(3) 0.029(2) C22 0.142(4) 0.082(3) 0.118(4) 0.009(3) 0.020(3) 0.019(3) C23 0.113(4) 0.147(4) 0.072(3) -0.017(3) 0.011(3) -0.012(4) _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 C9 1.224(4) . ? O2 C14 1.340(4) . ? O2 C15 1.471(4) . ? O3 C14 1.195(4) . ? O4 C19 1.349(4) . ? O4 C20 1.468(4) . ? O5 C19 1.194(4) . ? N1 C9 1.332(5) . ? N1 C7 1.452(5) . ? N2 C19 1.340(4) . ? N2 C13 1.459(4) . ? C1 C2 1.387(5) . ? C1 C6 1.388(5) . ? C1 C7 1.512(5) . ? C2 C3 1.400(7) . ? C3 C4 1.353(7) . ? C4 C5 1.343(7) . ? C5 C6 1.372(5) . ? C7 C8 1.530(5) . ? C9 C10 1.505(5) . ? C10 C11 1.513(5) . ? C10 C12 1.543(4) . ? C12 C13 1.517(5) . ? C13 C14 1.519(4) . ? C15 C17 1.507(6) . ? C15 C16 1.514(5) . ? C15 C18 1.524(5) . ? C20 C22 1.493(5) . ? C20 C23 1.498(5) . ? C20 C21 1.524(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 C14 O2 C15 120.7(3) . . ? C19 O4 C20 121.5(3) . . ? C9 N1 C7 124.8(3) . . ? C19 N2 C13 119.6(3) . . ? C2 C1 C6 117.7(4) . . ? C2 C1 C7 120.0(4) . . ? C6 C1 C7 122.3(3) . . ? C1 C2 C3 121.0(5) . . ? C4 C3 C2 118.4(5) . . ? C5 C4 C3 122.0(6) . . ? C4 C5 C6 120.3(5) . . ? C5 C6 C1 120.6(4) . . ? N1 C7 C1 113.0(3) . . ? N1 C7 C8 109.5(3) . . ? C1 C7 C8 111.9(3) . . ? O1 C9 N1 120.8(4) . . ? O1 C9 C10 122.5(3) . . ? N1 C9 C10 116.6(3) . . ? C9 C10 C11 110.5(3) . . ? C9 C10 C12 110.0(3) . . ? C11 C10 C12 110.0(3) . . ? C13 C12 C10 115.6(3) . . ? N2 C13 C12 111.3(3) . . ? N2 C13 C14 109.6(3) . . ? C12 C13 C14 112.4(3) . . ? O3 C14 O2 124.6(3) . . ? O3 C14 C13 125.2(3) . . ? O2 C14 C13 110.2(3) . . ? O2 C15 C17 108.5(3) . . ? O2 C15 C16 111.4(3) . . ? C17 C15 C16 113.6(3) . . ? O2 C15 C18 102.0(3) . . ? C17 C15 C18 110.5(4) . . ? C16 C15 C18 110.2(4) . . ? O5 C19 N2 124.8(4) . . ? O5 C19 O4 125.5(4) . . ? N2 C19 O4 109.6(3) . . ? O4 C20 C22 110.2(3) . . ? O4 C20 C23 109.7(3) . . ? C22 C20 C23 111.5(4) . . ? O4 C20 C21 101.2(3) . . ? C22 C20 C21 112.5(4) . . ? C23 C20 C21 111.4(4) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.97 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.136 _refine_diff_density_min -0.151 _refine_diff_density_rms 0.031 #===END data_(2)-apr1600 _database_code_depnum_ccdc_archive 'CCDC 224899' _audit_creation_date 2000-04-18T09:07:56-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.1beta5 _audit_conform_dict_location ftp://ftp.iucr.org/cifdics/cif_core_2.1beta5.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C6 H12 F1 N1 O2' _chemical_formula_structural 'C6 H12 F N O2' _chemical_formula_sum 'C6 H12 F N O2' _chemical_formula_weight 149.17 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1) _symmetry_space_group_name_Hall 'P 2yb' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.637(4) _cell_length_b 5.314(3) _cell_length_c 14.574(7) _cell_angle_alpha 90 _cell_angle_beta 93.10(3) _cell_angle_gamma 90 _cell_volume 745.3(6) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5334 _cell_measurement_theta_min 3.705 _cell_measurement_theta_max 22.722 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.01 _exptl_crystal_density_diffrn 1.33 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 320 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION NOT APPLIED # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.11 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_measurement_device KappaCCD _diffrn_measurement_method CCD _diffrn_reflns_number 3162 _diffrn_reflns_av_R_equivalents 0.1751 _diffrn_reflns_av_sigmaI/netI 0.23 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 4.08 _diffrn_reflns_theta_max 22.77 _diffrn_reflns_theta_full 22.77 _diffrn_measured_fraction_theta_full 0.988 _diffrn_measured_fraction_theta_max 0.988 _reflns_number_total 1844 _reflns_number_gt 853 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; ******* Diffraction was very weak ************************ For both independent molecules the F end of the chain showed large ADPs and for one of the molecules the disorder could be resolved between a major(76%) and a minor(24%) conformation. Hydrogen atoms on the N atoms were not located, and H atoms in the disordered region were omitted. 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^)+(0.0852P)^2^+0.4395P] 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_number_reflns 1844 _refine_ls_number_parameters 190 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.2149 _refine_ls_R_factor_gt 0.1075 _refine_ls_wR_factor_ref 0.2851 _refine_ls_wR_factor_gt 0.2256 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -4(5) _refine_diff_density_max 0.3 _refine_diff_density_min -0.229 _refine_diff_density_rms 0.065 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 -0.3422(13) 0.292(3) 0.5228(8) 0.158(6) Uani 1 1 d . . . O1 O -0.2288(9) 0.2059(16) 0.8802(6) 0.058(3) Uani 1 1 d . . . O2 O -0.1511(8) 0.5904(16) 0.9136(6) 0.049(2) Uani 1 1 d . . . N1 N -0.4119(9) 0.7889(19) 0.9012(7) 0.049(3) Uani 1 1 d . . . C1 C -0.2471(14) 0.441(3) 0.8843(8) 0.047(4) Uani 1 1 d . . . C2 C -0.3816(11) 0.549(2) 0.8494(8) 0.036(3) Uani 1 1 d . . . H2 H -0.4572 0.4245 0.859 0.043 Uiso 1 1 calc R . . C3 C -0.3847(13) 0.622(3) 0.7467(8) 0.053(4) Uani 1 1 d . . . H3B H -0.4705 0.7194 0.7314 0.064 Uiso 1 1 calc R . . H3A H -0.3046 0.7336 0.7365 0.064 Uiso 1 1 calc R . . C4 C -0.3797(14) 0.399(4) 0.6818(9) 0.070(5) Uani 1 1 d . . . H4 H -0.3038 0.2809 0.7029 0.084 Uiso 1 1 calc R . . C5 C -0.3501(19) 0.509(4) 0.5890(9) 0.103(7) Uani 1 1 d . . . H5B H -0.4252 0.6263 0.5682 0.123 Uiso 1 1 calc R . . H5A H -0.2611 0.6026 0.5929 0.123 Uiso 1 1 calc R . . C6 C -0.5184(17) 0.264(3) 0.6761(11) 0.087(5) Uani 1 1 d . . . H6C H -0.5361 0.1914 0.7361 0.131 Uiso 1 1 calc R . . H6B H -0.5164 0.1297 0.6301 0.131 Uiso 1 1 calc R . . H6A H -0.5923 0.3839 0.6583 0.131 Uiso 1 1 calc R . . O1A O 0.2776(8) -0.1883(18) 0.8646(6) 0.055(3) Uani 1 1 d . . . O2A O 0.3676(8) 0.1785(16) 0.9152(5) 0.051(3) Uani 1 1 d . . . N1A N 0.1159(10) 0.395(2) 0.9302(6) 0.044(3) Uani 1 1 d . . . C1A C 0.2639(13) 0.035(3) 0.8830(9) 0.048(4) Uani 1 1 d . . . C2A C 0.1270(12) 0.171(2) 0.8667(8) 0.043(4) Uani 1 1 d . . . H2A H 0.0501 0.0514 0.8788 0.052 Uiso 1 1 calc R . . C3A C 0.1081(13) 0.261(2) 0.7663(8) 0.048(4) Uani 1 1 d . B . H3A1 H 0.0214 0.3609 0.76 0.057 Uiso 1 1 calc R . . H3A2 H 0.1859 0.3756 0.7541 0.057 Uiso 1 1 calc R . . C4A C 0.1015(14) 0.060(3) 0.6931(11) 0.061(4) Uani 1 1 d . . . H4A H 0.1844 -0.0505 0.7057 0.074 Uiso 1 1 calc R A 1 C6A C -0.0241(16) -0.106(3) 0.6977(11) 0.080(5) Uani 1 1 d . B . H6A1 H -0.0208 -0.2384 0.651 0.12 Uiso 1 1 calc R . . H6A2 H -0.1084 -0.0055 0.6865 0.12 Uiso 1 1 calc R . . H6A3 H -0.0249 -0.1837 0.7588 0.12 Uiso 1 1 calc R . . C5A C 0.115(4) 0.167(11) 0.598(3) 0.14(3) Uani 0.76(3) 1 d P B 1 H5A1 H 0.1989 0.2731 0.5956 0.173 Uiso 0.76(3) 1 calc PR B 1 H5A2 H 0.1201 0.0302 0.552 0.173 Uiso 0.76(3) 1 calc PR B 1 F1A F -0.0059(19) 0.311(3) 0.5812(9) 0.111(7) Uani 0.76(3) 1 d P B 1 C5AA C 0.087(9) 0.190(14) 0.599(5) 0.011(18) Uiso 0.24(3) 1 d P B 2 F1AA F 0.189(5) 0.422(11) 0.576(3) 0.102(19) Uiso 0.24(3) 1 d P B 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.136(9) 0.241(17) 0.097(8) -0.010(10) 0.013(6) -0.033(11) O1 0.056(6) 0.028(7) 0.090(7) 0.006(5) 0.004(5) 0.002(5) O2 0.044(5) 0.032(6) 0.072(6) -0.014(5) 0.005(4) 0.004(5) N1 0.044(7) 0.041(8) 0.063(7) 0.001(6) 0.002(5) 0.012(6) C1 0.062(10) 0.030(9) 0.049(8) 0.013(7) -0.012(7) -0.012(8) C2 0.025(6) 0.023(8) 0.059(8) 0.009(7) 0.003(5) -0.001(6) C3 0.045(8) 0.068(11) 0.045(8) 0.007(8) -0.009(6) -0.008(8) C4 0.054(9) 0.111(14) 0.045(9) 0.002(10) -0.004(7) 0.028(10) C5 0.121(15) 0.16(2) 0.032(9) -0.042(12) 0.012(9) -0.018(14) C6 0.098(13) 0.083(14) 0.081(11) -0.030(10) 0.010(9) -0.026(11) O1A 0.046(6) 0.038(7) 0.080(7) -0.018(5) 0.006(5) 0.010(5) O2A 0.043(5) 0.053(7) 0.056(5) -0.002(5) -0.009(4) 0.001(5) N1A 0.052(6) 0.034(7) 0.048(7) -0.018(5) 0.003(5) 0.007(5) C1A 0.045(9) 0.054(11) 0.046(8) 0.007(8) 0.016(7) 0.031(8) C2A 0.042(8) 0.041(9) 0.046(8) 0.004(7) -0.010(6) -0.003(7) C3A 0.048(8) 0.036(9) 0.058(9) 0.005(7) -0.005(6) 0.000(6) C4A 0.044(9) 0.063(11) 0.075(12) -0.018(10) -0.005(8) 0.009(8) C6A 0.101(13) 0.053(11) 0.084(11) -0.012(10) -0.007(9) 0.001(10) C5A 0.08(3) 0.24(6) 0.12(3) -0.05(3) 0.00(2) 0.05(3) F1A 0.150(16) 0.102(12) 0.078(9) 0.012(8) -0.022(8) 0.001(12) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C5 1.51(2) . ? O1 C1 1.266(15) . ? O2 C1 1.274(14) . ? N1 C2 1.516(15) . ? C1 C2 1.482(16) . ? C2 C3 1.545(16) . ? C3 C4 1.52(2) . ? C4 C5 1.51(2) . ? C4 C6 1.52(2) . ? O1A C1A 1.223(15) . ? O2A C1A 1.325(16) . ? N1A C2A 1.515(15) . ? C1A C2A 1.514(16) . ? C2A C3A 1.539(15) . ? C3A C4A 1.509(18) . ? C4A C6A 1.503(18) . ? C4A C5A 1.51(5) . ? C4A C5AA 1.53(8) . ? C5A F1A 1.40(4) . ? C5AA F1AA 1.62(10) . ? 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 O1 C1 O2 122.0(13) . . ? O1 C1 C2 119.2(12) . . ? O2 C1 C2 118.7(12) . . ? C1 C2 N1 110.0(10) . . ? C1 C2 C3 113.6(10) . . ? N1 C2 C3 106.1(10) . . ? C4 C3 C2 114.1(11) . . ? C5 C4 C6 109.9(12) . . ? C5 C4 C3 105.6(14) . . ? C6 C4 C3 110.2(12) . . ? F1 C5 C4 107.2(16) . . ? O1A C1A O2A 123.3(11) . . ? O1A C1A C2A 122.2(14) . . ? O2A C1A C2A 114.4(12) . . ? C1A C2A N1A 111.7(10) . . ? C1A C2A C3A 110.9(10) . . ? N1A C2A C3A 109.1(10) . . ? C4A C3A C2A 116.8(11) . . ? C6A C4A C3A 112.8(12) . . ? C6A C4A C5A 112(2) . . ? C3A C4A C5A 112(3) . . ? C6A C4A C5AA 106(3) . . ? C3A C4A C5AA 108(3) . . ? C5A C4A C5AA 11(4) . . ? F1A C5A C4A 105(3) . . ? C4A C5AA F1AA 120(5) . . ? #===END