# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_datam _audit_creation_date 2013-01-01 _audit_creation_method ; Olex2 1.2 (compiled Nov 5 2012 18:22:26, GUI svn.r4372) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C6 H7 N2 O, C7 F5 O2' _chemical_formula_sum 'C13 H7 F5 N2 O3 ' _chemical_formula_weight 334.20 _chemical_melting_point ? 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' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _cell_length_a 10.421(4) _cell_length_b 10.421(3) _cell_length_c 12.704(3) _cell_angle_alpha 90.00 _cell_angle_beta 114.190(9) _cell_angle_gamma 90.00 _cell_volume 1258.5(7) _cell_formula_units_Z 4 _cell_measurement_reflns_used 9244 _cell_measurement_temperature 150 _cell_measurement_theta_max 27.8 _cell_measurement_theta_min 3.3 _exptl_absorpt_coefficient_mu 0.174 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.571 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_crystal_colour Colorless _exptl_crystal_density_diffrn 1.764 _exptl_crystal_density_meas ? _exptl_crystal_density_method "'not measured'" _exptl_crystal_description Prism _exptl_crystal_F_000 672 _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0618 _diffrn_reflns_av_unetI/netI 0.0480 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 11390 _diffrn_reflns_theta_full 27.48 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_min 3.52 _diffrn_ambient_temperature 150 _diffrn_detector CCD _diffrn_detector_area_resol_mean 13.6612 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_details ; scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 0.0000 XTD: 49.4000 2theta: 29.6000 scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 120.0000 XTD: 49.4000 2theta: 29.6000 scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 240.0000 XTD: 49.4000 2theta: 29.6000 ; _diffrn_measurement_device ; XtaLABmini: Fixed Chi 2 circle ; _diffrn_measurement_device_type ; Rigaku Mercury375R (2x2 bin mode) ; _diffrn_measurement_method 'profile data from \w-scans' _diffrn_measurement_specimen_support Fiber _diffrn_orient_matrix_type FS_PROCESS _diffrn_orient_matrix_UB_11 -0.051689 _diffrn_orient_matrix_UB_12 -0.066218 _diffrn_orient_matrix_UB_13 -0.076119 _diffrn_orient_matrix_UB_21 0.085016 _diffrn_orient_matrix_UB_22 -0.012750 _diffrn_orient_matrix_UB_23 0.011227 _diffrn_orient_matrix_UB_31 0.034258 _diffrn_orient_matrix_UB_32 -0.068270 _diffrn_orient_matrix_UB_33 0.071735 _diffrn_radiation_monochromator 'Graphite Monochromator' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_source 'Sealed Tube' _diffrn_source_current 12.0 _diffrn_source_power 0.6 _diffrn_source_voltage 50.0 _diffrn_special_details ; ? ; _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 2124 _reflns_number_total 2888 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009) ; _computing_data_collection ; CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _refine_diff_density_max 0.311 _refine_diff_density_min -0.233 _refine_diff_density_rms 0.060 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 236 _refine_ls_number_reflns 2888 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0696 _refine_ls_R_factor_gt 0.0485 _refine_ls_restrained_S_all 1.021 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0714P)^2^+0.0694P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1192 _refine_ls_wR_factor_ref 0.1315 _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. ; _olex2_refinement_description ; ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 H12 H 0.841(2) 0.775(2) 0.6706(17) 0.022(5) Uiso 1 1 d . . . H4 H 0.923(2) 1.153(2) 0.670(2) 0.040(7) Uiso 1 1 d . . . H13 H 0.778(3) 0.783(2) 0.466(2) 0.043(7) Uiso 1 1 d . . . H6 H 0.870(2) 1.144(2) 0.4794(18) 0.028(6) Uiso 1 1 d . . . H2A H 0.943(3) 1.085(3) 0.946(3) 0.055(8) Uiso 1 1 d . . . H2B H 0.877(3) 1.136(2) 0.825(2) 0.040(7) Uiso 1 1 d . . . H1 H 0.795(3) 0.963(2) 0.378(2) 0.043(7) Uiso 1 1 d . . . C1 C 0.3940(2) 0.74661(18) 0.44457(16) 0.0229(4) Uani 1 1 d . . . C2 C 0.4843(2) 0.69578(19) 0.64566(16) 0.0257(4) Uani 1 1 d . . . C3 C 0.3278(2) 0.62798(17) 0.41281(16) 0.0222(4) Uani 1 1 d . . . C4 C 0.8969(2) 1.0770(2) 0.63593(18) 0.0258(4) Uani 1 1 d . . . C5 C 0.3417(2) 0.54640(17) 0.50345(17) 0.0246(4) Uani 1 1 d . . . C6 C 0.8602(2) 1.07095(19) 0.51865(18) 0.0261(4) Uani 1 1 d . . . C7 C 0.8878(2) 0.96601(18) 0.69421(16) 0.0227(4) Uani 1 1 d . . . C8 C 0.4178(2) 0.57827(18) 0.61783(17) 0.0261(4) Uani 1 1 d . . . C9 C 0.9294(2) 0.96785(18) 0.82366(17) 0.0266(4) Uani 1 1 d . . . C10 C 0.4708(2) 0.78005(17) 0.55807(17) 0.0255(4) Uani 1 1 d . . . C11 C 0.2481(2) 0.59205(18) 0.28653(16) 0.0238(4) Uani 1 1 d . . . C12 C 0.8455(2) 0.85217(19) 0.63271(17) 0.0279(5) Uani 1 1 d . . . C13 C 0.8095(2) 0.8524(2) 0.51512(18) 0.0295(5) Uani 1 1 d . . . N1 N 0.81726(17) 0.96081(16) 0.46061(15) 0.0256(4) Uani 1 1 d . . . N2 N 0.9125(2) 1.07876(17) 0.86754(17) 0.0311(4) Uani 1 1 d . . . O1 O 0.97826(17) 0.86994(13) 0.88131(12) 0.0371(4) Uani 1 1 d . . . O2 O 0.25582(16) 0.47501(12) 0.26100(12) 0.0311(4) Uani 1 1 d . . . O3 O 0.18290(17) 0.67709(13) 0.21732(12) 0.0349(4) Uani 1 1 d . . . F1 F 0.38676(13) 0.83364(11) 0.36401(10) 0.0330(3) Uani 1 1 d . . . F2 F 0.53322(13) 0.89559(11) 0.58439(11) 0.0375(3) Uani 1 1 d . . . F3 F 0.56066(13) 0.72753(11) 0.75523(9) 0.0358(3) Uani 1 1 d . . . F4 F 0.42813(15) 0.49520(11) 0.70104(10) 0.0394(4) Uani 1 1 d . . . F5 F 0.27844(14) 0.43080(11) 0.48183(10) 0.0377(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0287(10) 0.0176(9) 0.0243(10) 0.0046(8) 0.0128(8) 0.0037(7) C2 0.0314(11) 0.0230(10) 0.0195(10) -0.0029(8) 0.0071(8) 0.0034(8) C3 0.0265(10) 0.0170(9) 0.0217(10) 0.0005(8) 0.0086(8) 0.0038(7) C4 0.0315(11) 0.0172(9) 0.0263(11) -0.0004(8) 0.0094(9) 0.0002(8) C5 0.0328(11) 0.0132(9) 0.0268(10) 0.0006(8) 0.0111(9) -0.0004(8) C6 0.0311(11) 0.0196(10) 0.0263(11) 0.0042(8) 0.0103(9) 0.0017(8) C7 0.0236(10) 0.0206(10) 0.0213(10) 0.0011(8) 0.0065(8) 0.0032(7) C8 0.0388(12) 0.0186(9) 0.0213(10) 0.0042(8) 0.0126(9) 0.0043(8) C9 0.0323(11) 0.0212(10) 0.0225(10) 0.0023(8) 0.0074(9) 0.0039(8) C10 0.0330(11) 0.0146(9) 0.0302(11) -0.0024(8) 0.0142(9) -0.0020(8) C11 0.0289(10) 0.0195(9) 0.0217(10) -0.0008(8) 0.0091(8) 0.0035(8) C12 0.0357(12) 0.0181(9) 0.0250(11) 0.0048(9) 0.0075(9) -0.0003(8) C13 0.0381(12) 0.0184(10) 0.0254(11) -0.0019(9) 0.0062(9) -0.0037(8) N1 0.0292(9) 0.0232(9) 0.0209(9) 0.0009(7) 0.0065(7) 0.0005(7) N2 0.0496(12) 0.0195(9) 0.0186(9) 0.0028(8) 0.0082(8) 0.0100(8) O1 0.0610(11) 0.0208(7) 0.0223(8) 0.0048(6) 0.0099(7) 0.0107(7) O2 0.0449(9) 0.0189(7) 0.0222(7) -0.0021(6) 0.0063(6) 0.0059(6) O3 0.0499(10) 0.0233(8) 0.0228(8) 0.0026(6) 0.0061(7) 0.0119(7) F1 0.0482(8) 0.0227(6) 0.0292(7) 0.0066(5) 0.0169(6) -0.0032(5) F2 0.0524(8) 0.0205(6) 0.0354(7) -0.0057(5) 0.0136(6) -0.0124(5) F3 0.0496(8) 0.0284(7) 0.0206(6) -0.0059(5) 0.0056(6) 0.0000(5) F4 0.0664(9) 0.0245(6) 0.0239(7) 0.0074(5) 0.0151(6) -0.0010(6) F5 0.0585(8) 0.0178(6) 0.0313(7) 0.0001(5) 0.0128(6) -0.0111(6) _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 C3 1.392(3) . ? C1 C10 1.377(3) . ? C1 F1 1.346(2) . ? C2 C8 1.380(3) . ? C2 C10 1.379(3) . ? C2 F3 1.331(2) . ? C3 C5 1.390(3) . ? C3 C11 1.521(3) . ? C4 H4 0.89(2) . ? C4 C6 1.380(3) . ? C4 C7 1.397(3) . ? C5 C8 1.381(3) . ? C5 F5 1.346(2) . ? C6 H6 0.94(2) . ? C6 N1 1.338(3) . ? C7 C9 1.519(3) . ? C7 C12 1.389(3) . ? C8 F4 1.336(2) . ? C9 N2 1.326(3) . ? C9 O1 1.237(2) . ? C10 F2 1.344(2) . ? C11 O2 1.273(2) . ? C11 O3 1.237(2) . ? C12 H12 0.95(2) . ? C12 C13 1.383(3) . ? C13 H13 0.93(3) . ? C13 N1 1.345(3) . ? N1 H1 0.98(2) . ? N2 H2A 0.92(3) . ? N2 H2B 0.79(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 C10 C1 C3 122.32(17) . . ? F1 C1 C3 120.73(17) . . ? F1 C1 C10 116.93(17) . . ? C10 C2 C8 118.94(18) . . ? F3 C2 C8 120.72(18) . . ? F3 C2 C10 120.34(18) . . ? C1 C3 C11 121.08(17) . . ? C5 C3 C1 115.58(17) . . ? C5 C3 C11 123.34(17) . . ? C6 C4 H4 117.5(15) . . ? C6 C4 C7 119.05(19) . . ? C7 C4 H4 123.4(15) . . ? C8 C5 C3 123.00(18) . . ? F5 C5 C3 120.13(17) . . ? F5 C5 C8 116.87(17) . . ? C4 C6 H6 119.5(13) . . ? N1 C6 H6 119.3(13) . . ? N1 C6 C4 121.08(19) . . ? C4 C7 C9 120.79(17) . . ? C12 C7 C4 118.92(18) . . ? C12 C7 C9 120.24(17) . . ? C2 C8 C5 119.64(18) . . ? F4 C8 C2 120.20(18) . . ? F4 C8 C5 120.15(17) . . ? N2 C9 C7 115.97(17) . . ? O1 C9 C7 119.73(17) . . ? O1 C9 N2 124.29(19) . . ? C1 C10 C2 120.49(18) . . ? F2 C10 C1 120.12(17) . . ? F2 C10 C2 119.39(18) . . ? O2 C11 C3 116.12(16) . . ? O3 C11 C3 118.50(16) . . ? O3 C11 O2 125.38(18) . . ? C7 C12 H12 120.6(12) . . ? C13 C12 H12 120.1(12) . . ? C13 C12 C7 119.27(18) . . ? C12 C13 H13 126.7(15) . . ? N1 C13 H13 112.6(15) . . ? N1 C13 C12 120.73(19) . . ? C6 N1 H1 116.9(14) . . ? C6 N1 C13 120.92(18) . . ? C13 N1 H1 122.2(14) . . ? H2A N2 H2B 124(3) . . ? C9 N2 H2A 118.3(17) . . ? C9 N2 H2B 118.0(18) . . ? _database_code_depnum_ccdc_archive 'CCDC 965660' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_datam _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H7 F4 N2 O3' _chemical_formula_weight 315.21 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 Monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.1699(7) _cell_length_b 10.3825(7) _cell_length_c 12.3583(9) _cell_angle_alpha 90.00 _cell_angle_beta 108.977(8) _cell_angle_gamma 90.00 _cell_volume 1233.98(15) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.697 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 636 _exptl_absorpt_coefficient_mu 0.161 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9533 _exptl_absorpt_correction_T_max 0.9809 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12858 _diffrn_reflns_av_R_equivalents 0.0327 _diffrn_reflns_av_sigmaI/netI 0.0240 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2822 _reflns_number_gt 2349 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0492P)^2^+0.5941P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2822 _refine_ls_number_parameters 234 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0503 _refine_ls_R_factor_gt 0.0400 _refine_ls_wR_factor_ref 0.1062 _refine_ls_wR_factor_gt 0.1003 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _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 F5 F 0.4093(15) 0.3255(14) -0.1171(11) 0.035(4) Uani 0.079(3) 1 d P . . H8 H 0.0871(18) 1.1673(18) 0.3322(15) 0.023(4) Uiso 1 1 d . . . H11 H 0.1533(19) 1.1545(19) 0.5271(16) 0.024(5) Uiso 1 1 d . . . H13 H 0.196(2) 0.780(2) 0.5288(17) 0.032(5) Uiso 1 1 d . . . H10 H 0.1327(19) 0.7746(19) 0.3304(16) 0.027(5) Uiso 1 1 d . . . H2A H 0.128(2) 1.141(2) 0.1675(18) 0.032(5) Uiso 1 1 d . . . H2B H 0.057(2) 1.089(2) 0.053(2) 0.042(6) Uiso 1 1 d . . . F4 F 0.55059(12) 0.39651(10) 0.08655(9) 0.0363(3) Uani 1 1 d . . . F1 F 0.27965(12) -0.06063(10) -0.01486(9) 0.0296(3) Uani 0.921(3) 1 d P . . F3 F 0.55705(11) 0.22655(11) 0.25401(8) 0.0350(3) Uani 1 1 d . . . O1 O 0.25409(13) -0.01106(11) -0.23583(9) 0.0257(3) Uani 1 1 d . . . H1 H 0.2292 -0.0183 -0.3074 0.039 Uiso 1 1 calc R . . F2 F 0.41631(13) 0.00179(11) 0.20129(9) 0.0406(3) Uani 1 1 d . . . O2 O 0.24494(13) 0.19912(11) -0.27547(9) 0.0270(3) Uani 1 1 d . . . C1 C 0.41345(17) 0.25427(16) -0.05407(13) 0.0219(3) Uani 1 1 d . . . C2 C 0.27427(16) 0.10925(15) -0.20798(13) 0.0200(3) Uani 1 1 d . . . C3 C 0.34442(16) 0.13626(15) -0.08287(12) 0.0196(3) Uani 1 1 d . . . C4 C 0.48706(17) 0.19839(17) 0.14489(13) 0.0255(4) Uani 1 1 d . . . C5 C 0.41673(18) 0.08356(16) 0.11779(13) 0.0261(4) Uani 1 1 d . . . C6 C 0.34568(17) 0.05260(16) 0.00464(13) 0.0231(3) Uani 1 1 d . . . C7 C 0.48405(17) 0.28324(16) 0.05844(13) 0.0237(3) Uani 1 1 d . . . O3 O 0.00093(14) 0.87631(11) 0.12077(10) 0.0298(3) Uani 1 1 d . . . N1 N 0.17926(14) 0.96760(13) 0.54295(11) 0.0218(3) Uani 1 1 d . . . N2 N 0.08277(16) 1.07977(14) 0.12951(12) 0.0259(3) Uani 1 1 d . . . C8 C 0.10719(17) 1.08379(15) 0.36655(13) 0.0208(3) Uani 1 1 d . . . C9 C 0.10099(16) 0.97024(15) 0.30559(13) 0.0196(3) Uani 1 1 d . . . C10 C 0.13279(18) 0.85515(16) 0.36580(14) 0.0240(3) Uani 1 1 d . . . C11 C 0.14719(16) 1.07798(16) 0.48491(13) 0.0219(3) Uani 1 1 d . . . C12 C 0.05775(16) 0.97139(15) 0.17646(13) 0.0209(3) Uani 1 1 d . . . C13 C 0.17169(18) 0.85751(16) 0.48414(14) 0.0255(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F5 0.046(8) 0.036(8) 0.026(7) -0.005(6) 0.014(6) -0.012(6) F4 0.0450(6) 0.0332(6) 0.0279(5) -0.0087(5) 0.0081(5) -0.0114(5) F1 0.0453(7) 0.0194(6) 0.0230(6) 0.0027(4) 0.0098(5) -0.0044(5) F3 0.0431(6) 0.0430(7) 0.0138(5) -0.0047(4) 0.0022(4) 0.0067(5) O1 0.0374(7) 0.0210(6) 0.0156(5) -0.0008(4) 0.0044(5) 0.0018(5) F2 0.0625(8) 0.0378(6) 0.0208(5) 0.0131(5) 0.0127(5) 0.0047(5) O2 0.0385(7) 0.0221(6) 0.0164(5) 0.0022(5) 0.0036(5) 0.0047(5) C1 0.0247(8) 0.0246(8) 0.0173(7) -0.0001(7) 0.0079(6) 0.0035(6) C2 0.0215(7) 0.0216(8) 0.0170(7) 0.0020(6) 0.0062(6) 0.0047(6) C3 0.0212(7) 0.0218(8) 0.0161(7) 0.0005(6) 0.0063(6) 0.0051(6) C4 0.0275(8) 0.0335(9) 0.0135(7) -0.0022(6) 0.0041(6) 0.0089(7) C5 0.0349(9) 0.0271(9) 0.0173(7) 0.0075(6) 0.0098(7) 0.0087(7) C6 0.0287(8) 0.0207(8) 0.0204(8) 0.0017(6) 0.0086(6) 0.0042(6) C7 0.0254(8) 0.0246(8) 0.0212(8) -0.0030(6) 0.0080(6) 0.0010(6) O3 0.0456(7) 0.0215(6) 0.0188(6) -0.0040(5) 0.0059(5) -0.0100(5) N1 0.0241(7) 0.0237(7) 0.0163(6) -0.0004(5) 0.0046(5) -0.0009(5) N2 0.0389(8) 0.0216(8) 0.0148(7) -0.0031(6) 0.0056(6) -0.0103(6) C8 0.0252(8) 0.0184(8) 0.0176(7) 0.0000(6) 0.0053(6) -0.0005(6) C9 0.0194(7) 0.0218(8) 0.0167(7) -0.0012(6) 0.0047(6) -0.0038(6) C10 0.0318(9) 0.0184(8) 0.0206(8) -0.0023(6) 0.0066(7) -0.0010(6) C11 0.0241(8) 0.0227(8) 0.0188(7) -0.0038(6) 0.0066(6) -0.0010(6) C12 0.0250(8) 0.0198(8) 0.0174(7) -0.0019(6) 0.0062(6) -0.0006(6) C13 0.0337(9) 0.0201(8) 0.0209(8) 0.0013(6) 0.0065(7) 0.0011(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 F5 C1 1.065(14) . ? F4 C7 1.3449(19) . ? F1 C6 1.336(2) . ? F3 C4 1.3366(17) . ? O1 C2 1.2942(19) . ? O1 H1 0.8400 . ? F2 C5 1.3374(18) . ? O2 C2 1.2221(19) . ? C1 C7 1.375(2) . ? C1 C3 1.399(2) . ? C2 C3 1.504(2) . ? C3 C6 1.384(2) . ? C4 C5 1.375(3) . ? C4 C7 1.377(2) . ? C5 C6 1.387(2) . ? O3 C12 1.2343(19) . ? N1 C11 1.335(2) . ? N1 C13 1.343(2) . ? N2 C12 1.328(2) . ? N2 H2A 0.83(2) . ? N2 H2B 0.90(2) . ? C8 C11 1.386(2) . ? C8 C9 1.389(2) . ? C8 H8 0.958(19) . ? C9 C10 1.389(2) . ? C9 C12 1.511(2) . ? C10 C13 1.386(2) . ? C10 H10 0.94(2) . ? C11 H11 0.94(2) . ? C13 H13 0.97(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 C2 O1 H1 109.5 . . ? F5 C1 C7 118.1(7) . . ? F5 C1 C3 121.7(7) . . ? C7 C1 C3 120.17(15) . . ? O2 C2 O1 124.96(14) . . ? O2 C2 C3 119.23(14) . . ? O1 C2 C3 115.76(13) . . ? C6 C3 C1 118.32(14) . . ? C6 C3 C2 124.56(14) . . ? C1 C3 C2 117.12(14) . . ? F3 C4 C5 119.99(15) . . ? F3 C4 C7 120.85(16) . . ? C5 C4 C7 119.16(14) . . ? F2 C5 C4 119.64(15) . . ? F2 C5 C6 119.97(16) . . ? C4 C5 C6 120.39(15) . . ? F1 C6 C3 122.33(14) . . ? F1 C6 C5 116.88(14) . . ? C3 C6 C5 120.78(15) . . ? F4 C7 C1 120.40(15) . . ? F4 C7 C4 118.46(14) . . ? C1 C7 C4 121.14(16) . . ? C11 N1 C13 118.60(13) . . ? C12 N2 H2A 123.2(14) . . ? C12 N2 H2B 121.0(14) . . ? H2A N2 H2B 116(2) . . ? C11 C8 C9 118.77(14) . . ? C11 C8 H8 117.0(11) . . ? C9 C8 H8 124.2(11) . . ? C10 C9 C8 118.54(14) . . ? C10 C9 C12 120.63(14) . . ? C8 C9 C12 120.81(13) . . ? C13 C10 C9 119.14(15) . . ? C13 C10 H10 117.5(11) . . ? C9 C10 H10 123.3(11) . . ? N1 C11 C8 122.75(15) . . ? N1 C11 H11 117.8(11) . . ? C8 C11 H11 119.5(11) . . ? O3 C12 N2 123.75(15) . . ? O3 C12 C9 120.35(14) . . ? N2 C12 C9 115.89(14) . . ? N1 C13 C10 122.19(15) . . ? N1 C13 H13 116.4(12) . . ? C10 C13 H13 121.4(12) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.357 _refine_diff_density_min -0.266 _refine_diff_density_rms 0.049 _database_code_depnum_ccdc_archive 'CCDC 965661' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_datam _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H9 F3 N2 O3' _chemical_formula_weight 298.22 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 Monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.1728(12) _cell_length_b 10.4501(13) _cell_length_c 12.2561(15) _cell_angle_alpha 90.00 _cell_angle_beta 109.116(8) _cell_angle_gamma 90.00 _cell_volume 1231.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.609 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.145 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9716 _exptl_absorpt_correction_T_max 0.9828 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12048 _diffrn_reflns_av_R_equivalents 0.0262 _diffrn_reflns_av_sigmaI/netI 0.0198 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.46 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2808 _reflns_number_gt 2392 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0491P)^2^+0.5409P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2808 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0478 _refine_ls_R_factor_gt 0.0393 _refine_ls_wR_factor_ref 0.1011 _refine_ls_wR_factor_gt 0.0965 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _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 O3 O 0.50470(12) 0.38064(10) 0.12212(8) 0.0278(3) Uani 1 1 d . . . N1 N 0.68231(13) 0.47142(12) 0.54769(10) 0.0219(3) Uani 1 1 d . . . N2 N 0.57840(15) 0.58570(12) 0.12966(11) 0.0252(3) Uani 1 1 d . . . C1 C 0.55808(15) 0.47647(13) 0.17763(12) 0.0202(3) Uani 1 1 d . . . C2 C 0.60300(14) 0.47573(13) 0.30787(12) 0.0189(3) Uani 1 1 d . . . C3 C 0.60521(15) 0.58749(14) 0.36978(12) 0.0211(3) Uani 1 1 d . . . C4 C 0.64005(16) 0.36139(14) 0.36831(13) 0.0235(3) Uani 1 1 d . . . C5 C 0.64605(15) 0.58074(14) 0.48909(12) 0.0215(3) Uani 1 1 d . . . C6 C 0.67923(16) 0.36335(15) 0.48777(12) 0.0253(3) Uani 1 1 d . . . O1 O 0.74640(11) 0.80142(10) 0.23614(9) 0.0265(2) Uani 1 1 d . . . O2 O 0.75230(12) 1.01107(10) 0.27283(9) 0.0254(2) Uani 1 1 d . . . F1 F 0.77327(11) 1.06271(9) 0.49400(8) 0.0363(3) Uani 1 1 d . . . F3 F 1.05972(11) 0.78985(11) 0.77116(8) 0.0421(3) Uani 1 1 d . . . F2 F 0.91176(13) 1.00665(11) 0.71415(9) 0.0474(3) Uani 1 1 d . . . C7 C 0.84394(14) 0.86746(14) 0.43000(11) 0.0206(3) Uani 1 1 d . . . C8 C 0.91735(16) 0.75275(16) 0.46233(13) 0.0258(3) Uani 1 1 d . . . C9 C 0.77379(14) 0.89140(14) 0.30351(12) 0.0200(3) Uani 1 1 d . . . C10 C 0.98870(16) 0.81202(17) 0.65925(13) 0.0295(4) Uani 1 1 d . . . C11 C 0.84315(16) 0.95234(14) 0.51635(13) 0.0243(3) Uani 1 1 d . . . C12 C 0.99077(17) 0.72481(17) 0.57646(14) 0.0299(4) Uani 1 1 d . . . C13 C 0.91488(17) 0.92422(16) 0.63140(12) 0.0281(3) Uani 1 1 d . . . H4 H 0.6405(18) 0.2824(17) 0.3309(15) 0.027(4) Uiso 1 1 d . . . H8 H 0.9171(18) 0.6916(17) 0.4060(15) 0.027(4) Uiso 1 1 d . . . H6 H 0.703(2) 0.2877(19) 0.5342(17) 0.038(5) Uiso 1 1 d . . . H3 H 0.5829(18) 0.6680(18) 0.3364(15) 0.028(4) Uiso 1 1 d . . . H5 H 0.6464(18) 0.6570(18) 0.5311(16) 0.030(5) Uiso 1 1 d . . . H2A H 0.6246(19) 0.6476(19) 0.1721(16) 0.032(5) Uiso 1 1 d . . . H12 H 1.041(2) 0.644(2) 0.5976(18) 0.046(6) Uiso 1 1 d . . . H2B H 0.552(2) 0.5923(19) 0.0532(19) 0.042(5) Uiso 1 1 d . . . H2 H 0.725(3) 1.023(2) 0.192(2) 0.073(8) 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 O3 0.0433(7) 0.0206(5) 0.0167(5) -0.0042(4) 0.0060(4) -0.0090(5) N1 0.0246(6) 0.0235(6) 0.0164(5) -0.0008(5) 0.0049(5) -0.0006(5) N2 0.0382(7) 0.0215(6) 0.0133(6) -0.0033(5) 0.0050(5) -0.0086(5) C1 0.0245(7) 0.0201(7) 0.0153(6) -0.0015(5) 0.0057(5) -0.0008(5) C2 0.0189(6) 0.0215(7) 0.0156(6) -0.0017(5) 0.0046(5) -0.0031(5) C3 0.0266(7) 0.0184(7) 0.0180(7) 0.0008(5) 0.0068(6) -0.0002(5) C4 0.0297(8) 0.0184(7) 0.0205(7) -0.0031(6) 0.0060(6) 0.0006(6) C5 0.0253(7) 0.0211(7) 0.0179(7) -0.0033(5) 0.0069(5) -0.0018(6) C6 0.0323(8) 0.0211(7) 0.0197(7) 0.0020(6) 0.0048(6) 0.0025(6) O1 0.0373(6) 0.0223(5) 0.0174(5) -0.0024(4) 0.0057(4) -0.0050(4) O2 0.0360(6) 0.0209(5) 0.0162(5) 0.0003(4) 0.0044(4) -0.0032(4) F1 0.0550(7) 0.0249(5) 0.0278(5) -0.0038(4) 0.0117(4) 0.0036(4) F3 0.0411(6) 0.0612(7) 0.0170(4) 0.0097(4) 0.0001(4) -0.0099(5) F2 0.0711(8) 0.0458(6) 0.0223(5) -0.0138(4) 0.0115(5) -0.0096(6) C7 0.0205(7) 0.0253(7) 0.0156(6) 0.0002(5) 0.0052(5) -0.0061(5) C8 0.0267(8) 0.0309(8) 0.0201(7) 0.0017(6) 0.0080(6) -0.0005(6) C9 0.0200(7) 0.0229(7) 0.0167(6) -0.0003(5) 0.0054(5) -0.0045(5) C10 0.0252(7) 0.0440(9) 0.0165(7) 0.0060(6) 0.0032(6) -0.0105(7) C11 0.0280(8) 0.0225(7) 0.0219(7) -0.0012(6) 0.0073(6) -0.0057(6) C12 0.0277(8) 0.0356(9) 0.0267(8) 0.0087(7) 0.0092(6) 0.0034(7) C13 0.0340(8) 0.0327(8) 0.0176(7) -0.0060(6) 0.0083(6) -0.0121(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 O3 C1 1.2324(17) . ? N1 C5 1.3355(19) . ? N1 C6 1.3418(19) . ? N2 C1 1.3307(19) . ? N2 H2A 0.87(2) . ? N2 H2B 0.89(2) . ? C1 C2 1.5097(19) . ? C2 C3 1.3889(19) . ? C2 C4 1.391(2) . ? C3 C5 1.3848(19) . ? C3 H3 0.931(18) . ? C4 C6 1.386(2) . ? C4 H4 0.945(18) . ? C5 H5 0.948(19) . ? C6 H6 0.96(2) . ? O1 C9 1.2219(17) . ? O2 C9 1.3036(17) . ? O2 H2 0.95(3) . ? F1 C11 1.3353(18) . ? F3 C10 1.3446(17) . ? F2 C13 1.3390(18) . ? C7 C11 1.383(2) . ? C7 C8 1.399(2) . ? C7 C9 1.5002(18) . ? C8 C12 1.384(2) . ? C8 H8 0.940(18) . ? C10 C12 1.369(2) . ? C10 C13 1.374(2) . ? C11 C13 1.390(2) . ? C12 H12 0.98(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 C5 N1 C6 118.22(12) . . ? C1 N2 H2A 120.5(12) . . ? C1 N2 H2B 119.7(13) . . ? H2A N2 H2B 119.4(18) . . ? O3 C1 N2 123.87(13) . . ? O3 C1 C2 120.37(12) . . ? N2 C1 C2 115.75(12) . . ? C3 C2 C4 118.57(13) . . ? C3 C2 C1 121.23(12) . . ? C4 C2 C1 120.19(12) . . ? C5 C3 C2 118.66(13) . . ? C5 C3 H3 117.1(11) . . ? C2 C3 H3 124.2(11) . . ? C6 C4 C2 118.93(13) . . ? C6 C4 H4 118.7(10) . . ? C2 C4 H4 122.3(10) . . ? N1 C5 C3 123.09(13) . . ? N1 C5 H5 118.4(11) . . ? C3 C5 H5 118.5(11) . . ? N1 C6 C4 122.53(14) . . ? N1 C6 H6 114.5(12) . . ? C4 C6 H6 123.0(12) . . ? C9 O2 H2 113.3(15) . . ? C11 C7 C8 117.98(13) . . ? C11 C7 C9 124.32(13) . . ? C8 C7 C9 117.68(13) . . ? C12 C8 C7 121.88(15) . . ? C12 C8 H8 118.0(11) . . ? C7 C8 H8 120.1(11) . . ? O1 C9 O2 124.31(13) . . ? O1 C9 C7 119.74(13) . . ? O2 C9 C7 115.86(12) . . ? F3 C10 C12 120.52(15) . . ? F3 C10 C13 117.89(15) . . ? C12 C10 C13 121.58(14) . . ? F1 C11 C7 122.22(13) . . ? F1 C11 C13 117.25(13) . . ? C7 C11 C13 120.52(14) . . ? C10 C12 C8 118.33(15) . . ? C10 C12 H12 120.9(12) . . ? C8 C12 H12 120.8(12) . . ? F2 C13 C10 120.50(14) . . ? F2 C13 C11 119.83(15) . . ? C10 C13 C11 119.67(14) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.341 _refine_diff_density_min -0.275 _refine_diff_density_rms 0.045 _database_code_depnum_ccdc_archive 'CCDC 965662' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_datam _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H9 F3 N2 O3' _chemical_formula_weight 298.22 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 Monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.4383(9) _cell_length_b 10.2939(9) _cell_length_c 12.3077(10) _cell_angle_alpha 90.00 _cell_angle_beta 110.475(8) _cell_angle_gamma 90.00 _cell_volume 1238.92(18) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Plate _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.599 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.144 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9446 _exptl_absorpt_correction_T_max 0.9857 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12810 _diffrn_reflns_av_R_equivalents 0.0382 _diffrn_reflns_av_sigmaI/netI 0.0277 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.42 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2823 _reflns_number_gt 2212 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0513P)^2^+0.4172P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2823 _refine_ls_number_parameters 223 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0587 _refine_ls_R_factor_gt 0.0424 _refine_ls_wR_factor_ref 0.1066 _refine_ls_wR_factor_gt 0.0993 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _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 H13 H 0.585(2) 0.498(2) 0.3096(18) 0.041(6) Uiso 1 1 d . . . H8 H 0.5887(19) 0.8109(18) 0.5871(16) 0.032(5) Uiso 1 1 d . . . H6 H 0.8525(18) -0.1611(18) 0.4664(15) 0.024(4) Uiso 1 1 d . . . H9 H 0.808(2) 0.2142(19) 0.4646(17) 0.032(5) Uiso 1 1 d . . . H7 H 0.8672(17) 0.2219(17) 0.6671(15) 0.022(4) Uiso 1 1 d . . . H4 H 0.9161(19) -0.1727(19) 0.6660(16) 0.028(5) Uiso 1 1 d . . . H2A H 0.8650(19) -0.1474(19) 0.8251(16) 0.025(5) Uiso 1 1 d . . . H2B H 0.940(2) -0.0897(19) 0.9418(19) 0.035(5) Uiso 1 1 d . . . C1 C 0.94211(16) 0.02415(15) 0.82169(13) 0.0207(3) Uani 1 1 d . . . C2 C 0.89914(15) 0.02485(15) 0.69088(13) 0.0195(3) Uani 1 1 d . . . C3 C 0.72640(16) 0.60441(16) 0.69346(13) 0.0203(3) Uani 1 1 d . . . C4 C 0.89410(17) -0.08905(16) 0.62933(13) 0.0218(3) Uani 1 1 d . . . C5 C 0.65422(17) 0.53827(17) 0.47951(14) 0.0260(4) Uani 1 1 d . . . C6 C 0.85535(16) -0.08285(16) 0.50999(13) 0.0216(3) Uani 1 1 d . . . C7 C 0.86662(18) 0.14111(16) 0.63018(14) 0.0244(4) Uani 1 1 d . . . C8 C 0.58908(17) 0.74364(18) 0.53069(14) 0.0266(4) Uani 1 1 d . . . C9 C 0.82937(18) 0.13878(17) 0.51017(14) 0.0266(4) Uani 1 1 d . . . C10 C 0.65753(16) 0.62603(16) 0.56551(13) 0.0213(3) Uani 1 1 d . . . C11 C 0.51686(18) 0.6778(2) 0.33272(14) 0.0340(5) Uani 1 1 d . . . C12 C 0.51919(18) 0.76801(19) 0.41541(16) 0.0320(4) Uani 1 1 d . . . C13 C 0.58439(19) 0.5622(2) 0.36239(15) 0.0328(4) Uani 1 1 d . . . N1 N 0.82345(14) 0.02814(13) 0.45078(11) 0.0222(3) Uani 1 1 d . . . N2 N 0.91600(16) -0.08439(14) 0.86831(13) 0.0261(3) Uani 1 1 d . . . O1 O 0.75452(12) 0.48485(11) 0.72633(9) 0.0258(3) Uani 1 1 d . . . H1 H 0.7787 0.4805 0.7989 0.039 Uiso 1 1 calc R . . O2 O 0.74809(12) 0.69725(11) 0.75969(9) 0.0275(3) Uani 1 1 d . . . O3 O 0.99879(13) 0.11983(11) 0.87865(9) 0.0291(3) Uani 1 1 d . . . F1 F 0.72138(13) 0.42459(10) 0.50682(9) 0.0410(3) Uani 1 1 d . . . F2 F 0.44619(12) 0.70453(14) 0.22048(9) 0.0502(4) Uani 1 1 d . . . F3 F 0.45312(13) 0.88271(13) 0.38157(10) 0.0531(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0252(8) 0.0209(8) 0.0159(7) -0.0016(6) 0.0070(6) 0.0000(6) C2 0.0193(7) 0.0211(8) 0.0174(7) -0.0008(6) 0.0056(6) -0.0024(6) C3 0.0194(7) 0.0236(8) 0.0166(7) 0.0004(6) 0.0048(6) -0.0041(6) C4 0.0263(8) 0.0191(8) 0.0192(8) -0.0002(6) 0.0071(6) -0.0005(7) C5 0.0289(9) 0.0261(9) 0.0225(8) -0.0017(7) 0.0084(7) -0.0054(7) C6 0.0252(8) 0.0211(8) 0.0177(7) -0.0037(6) 0.0066(6) -0.0002(6) C7 0.0322(9) 0.0187(8) 0.0201(8) -0.0029(6) 0.0064(7) -0.0006(7) C8 0.0273(9) 0.0313(9) 0.0216(8) 0.0036(7) 0.0092(7) 0.0007(7) C9 0.0339(9) 0.0224(9) 0.0205(8) 0.0027(7) 0.0055(7) 0.0027(7) C10 0.0200(8) 0.0260(9) 0.0175(8) 0.0013(6) 0.0058(6) -0.0049(7) C11 0.0256(9) 0.0572(13) 0.0147(8) 0.0102(8) 0.0014(7) -0.0095(9) C12 0.0257(9) 0.0428(11) 0.0279(9) 0.0131(8) 0.0098(7) 0.0050(8) C13 0.0364(10) 0.0435(11) 0.0180(8) -0.0067(8) 0.0088(7) -0.0137(9) N1 0.0250(7) 0.0229(7) 0.0163(6) -0.0007(5) 0.0043(5) 0.0003(6) N2 0.0405(9) 0.0213(8) 0.0145(7) -0.0045(6) 0.0071(6) -0.0105(7) O1 0.0369(7) 0.0227(6) 0.0139(5) 0.0002(5) 0.0041(5) -0.0020(5) O2 0.0402(7) 0.0225(6) 0.0165(5) -0.0024(5) 0.0058(5) -0.0033(5) O3 0.0456(7) 0.0215(6) 0.0170(6) -0.0040(5) 0.0070(5) -0.0094(5) F1 0.0633(8) 0.0294(6) 0.0292(6) -0.0059(5) 0.0148(5) 0.0048(5) F2 0.0403(7) 0.0848(10) 0.0172(5) 0.0138(6) 0.0000(5) -0.0109(6) F3 0.0539(8) 0.0621(8) 0.0417(7) 0.0277(6) 0.0147(6) 0.0265(6) _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 O3 1.2334(19) . ? C1 N2 1.327(2) . ? C1 C2 1.513(2) . ? C2 C4 1.387(2) . ? C2 C7 1.389(2) . ? C3 O2 1.2248(19) . ? C3 O1 1.2967(19) . ? C3 C10 1.501(2) . ? C4 C6 1.382(2) . ? C4 H4 0.962(19) . ? C5 F1 1.345(2) . ? C5 C10 1.383(2) . ? C5 C13 1.391(2) . ? C6 N1 1.333(2) . ? C6 H6 0.962(19) . ? C7 C9 1.390(2) . ? C7 H7 0.947(18) . ? C8 C12 1.373(2) . ? C8 C10 1.395(2) . ? C8 H8 0.982(19) . ? C9 N1 1.343(2) . ? C9 H9 0.94(2) . ? C11 F2 1.3473(19) . ? C11 C13 1.366(3) . ? C11 C12 1.372(3) . ? C12 F3 1.357(2) . ? C13 H13 0.93(2) . ? N2 H2A 0.888(19) . ? N2 H2B 0.85(2) . ? O1 H1 0.8400 . ? 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 O3 C1 N2 123.83(14) . . ? O3 C1 C2 120.39(14) . . ? N2 C1 C2 115.78(14) . . ? C4 C2 C7 118.64(14) . . ? C4 C2 C1 121.19(14) . . ? C7 C2 C1 120.16(14) . . ? O2 C3 O1 124.33(14) . . ? O2 C3 C10 119.45(14) . . ? O1 C3 C10 116.17(14) . . ? C6 C4 C2 118.85(15) . . ? C6 C4 H4 118.2(11) . . ? C2 C4 H4 122.9(11) . . ? F1 C5 C10 120.39(14) . . ? F1 C5 C13 116.83(16) . . ? C10 C5 C13 122.78(17) . . ? N1 C6 C4 123.02(15) . . ? N1 C6 H6 117.3(11) . . ? C4 C6 H6 119.6(11) . . ? C2 C7 C9 118.80(15) . . ? C2 C7 H7 122.7(10) . . ? C9 C7 H7 118.5(10) . . ? C12 C8 C10 120.41(17) . . ? C12 C8 H8 118.0(11) . . ? C10 C8 H8 121.6(11) . . ? N1 C9 C7 122.38(16) . . ? N1 C9 H9 114.8(12) . . ? C7 C9 H9 122.8(12) . . ? C5 C10 C8 117.32(15) . . ? C5 C10 C3 125.49(15) . . ? C8 C10 C3 117.18(14) . . ? F2 C11 C13 119.90(18) . . ? F2 C11 C12 118.91(18) . . ? C13 C11 C12 121.19(16) . . ? F3 C12 C11 119.08(16) . . ? F3 C12 C8 120.36(18) . . ? C11 C12 C8 120.55(17) . . ? C11 C13 C5 117.74(17) . . ? C11 C13 H13 124.1(13) . . ? C5 C13 H13 118.1(13) . . ? C6 N1 C9 118.30(13) . . ? C1 N2 H2A 121.8(12) . . ? C1 N2 H2B 119.1(14) . . ? H2A N2 H2B 118.7(18) . . ? C3 O1 H1 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.277 _refine_diff_density_min -0.255 _refine_diff_density_rms 0.047 _database_code_depnum_ccdc_archive 'CCDC 965663' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_datam _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H9 F3 N2 O3' _chemical_formula_weight 298.22 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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.2331(14) _cell_length_b 7.7199(15) _cell_length_c 12.597(2) _cell_angle_alpha 73.687(5) _cell_angle_beta 84.340(6) _cell_angle_gamma 66.993(5) _cell_volume 621.4(2) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.594 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 304 _exptl_absorpt_coefficient_mu 0.144 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9514 _exptl_absorpt_correction_T_max 0.9830 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6167 _diffrn_reflns_av_R_equivalents 0.0339 _diffrn_reflns_av_sigmaI/netI 0.0431 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2832 _reflns_number_gt 2177 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0620P)^2^+0.1004P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2832 _refine_ls_number_parameters 223 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0646 _refine_ls_R_factor_gt 0.0474 _refine_ls_wR_factor_ref 0.1216 _refine_ls_wR_factor_gt 0.1133 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 C8 C 0.1530(2) 0.8449(2) 0.81816(13) 0.0205(3) Uani 1 1 d . . . C10 C 0.2159(3) 0.6411(2) 0.89334(14) 0.0232(4) Uani 1 1 d . . . C11 C 0.4614(3) 0.7583(2) 0.38266(13) 0.0226(4) Uani 1 1 d . . . C12 C 0.4167(2) 0.9480(2) 0.29311(13) 0.0201(3) Uani 1 1 d . . . C13 C 0.1427(3) 1.0043(2) 0.85377(13) 0.0225(4) Uani 1 1 d . . . C14 C 0.3925(3) 1.1147(2) 0.32373(14) 0.0230(4) Uani 1 1 d . . . C15 C 0.1009(2) 0.8901(2) 0.70671(13) 0.0227(4) Uani 1 1 d . . . C16 C 0.3891(3) 0.9640(2) 0.18212(13) 0.0226(4) Uani 1 1 d . . . C17 C 0.0851(3) 1.1933(3) 0.78727(15) 0.0271(4) Uani 1 1 d . . . C18 C 0.0428(3) 1.0751(3) 0.63611(15) 0.0274(4) Uani 1 1 d . . . C19 C 0.3404(3) 1.2906(3) 0.24440(14) 0.0251(4) Uani 1 1 d . . . C20 C 0.3355(3) 1.1462(2) 0.10777(14) 0.0241(4) Uani 1 1 d . . . C21 C 0.0361(3) 1.2223(3) 0.67908(15) 0.0277(4) Uani 1 1 d . . . N0AA N 0.5368(2) 0.5935(2) 0.35205(13) 0.0289(4) Uani 1 1 d . . . N N 0.3101(2) 1.3074(2) 0.13746(11) 0.0235(3) Uani 1 1 d . . . O O 0.4205(2) 0.76590(17) 0.47944(9) 0.0297(3) Uani 1 1 d . . . O4 O 0.3030(2) 0.49604(18) 0.85986(10) 0.0329(3) Uani 1 1 d . . . O5 O 0.1659(2) 0.63888(18) 0.99542(10) 0.0339(3) Uani 1 1 d . . . H5 H 0.2185 0.5246 1.0358 0.051 Uiso 1 1 calc R . . F1 F 0.10008(16) 0.74594(15) 0.66616(8) 0.0312(3) Uani 1 1 d . . . F2 F 0.20014(16) 0.97352(15) 0.95804(8) 0.0308(3) Uani 1 1 d . . . F6 F -0.02233(19) 1.40566(15) 0.61217(9) 0.0438(3) Uani 1 1 d . . . H0AA H 0.581(3) 0.589(3) 0.2864(19) 0.039(6) Uiso 1 1 d . . . H0AB H 0.565(4) 0.482(4) 0.407(2) 0.059(7) Uiso 1 1 d . . . H14 H 0.408(3) 1.116(3) 0.3946(16) 0.026(5) Uiso 1 1 d . . . H16 H 0.406(3) 0.852(3) 0.1559(16) 0.031(5) Uiso 1 1 d . . . H17 H 0.080(3) 1.298(3) 0.8179(18) 0.043(6) Uiso 1 1 d . . . H18 H 0.009(3) 1.098(3) 0.563(2) 0.050(7) Uiso 1 1 d . . . H19 H 0.319(3) 1.410(3) 0.2621(16) 0.031(5) Uiso 1 1 d . . . H20 H 0.320(3) 1.160(3) 0.0319(19) 0.049(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 C8 0.0189(8) 0.0229(8) 0.0174(8) -0.0046(7) 0.0017(6) -0.0063(6) C10 0.0230(8) 0.0259(9) 0.0195(8) -0.0065(7) 0.0017(6) -0.0081(7) C11 0.0260(9) 0.0226(8) 0.0174(8) -0.0036(7) 0.0002(7) -0.0083(7) C12 0.0205(8) 0.0213(8) 0.0162(7) -0.0039(6) 0.0015(6) -0.0065(6) C13 0.0241(9) 0.0282(9) 0.0161(8) -0.0071(7) 0.0016(6) -0.0104(7) C14 0.0289(9) 0.0235(9) 0.0156(8) -0.0063(7) 0.0013(7) -0.0084(7) C15 0.0216(8) 0.0267(9) 0.0199(8) -0.0099(7) 0.0031(7) -0.0073(7) C16 0.0281(9) 0.0213(8) 0.0188(8) -0.0062(7) 0.0008(7) -0.0093(7) C17 0.0305(10) 0.0239(9) 0.0268(9) -0.0073(7) 0.0042(7) -0.0106(7) C18 0.0288(9) 0.0316(10) 0.0172(8) -0.0037(7) -0.0014(7) -0.0081(8) C19 0.0319(9) 0.0225(9) 0.0219(8) -0.0070(7) 0.0021(7) -0.0112(7) C20 0.0305(10) 0.0249(9) 0.0164(8) -0.0033(7) -0.0016(7) -0.0110(7) C21 0.0285(9) 0.0223(9) 0.0235(9) 0.0012(7) 0.0028(7) -0.0062(7) N0AA 0.0428(10) 0.0203(8) 0.0167(7) -0.0028(6) 0.0064(7) -0.0074(7) N 0.0288(8) 0.0215(7) 0.0178(7) -0.0022(6) 0.0002(6) -0.0092(6) O 0.0455(8) 0.0240(6) 0.0157(6) -0.0037(5) 0.0027(5) -0.0107(6) O4 0.0481(8) 0.0224(6) 0.0239(6) -0.0078(5) 0.0047(6) -0.0087(6) O5 0.0508(9) 0.0218(6) 0.0164(6) -0.0015(5) 0.0041(6) -0.0037(6) F1 0.0397(6) 0.0317(6) 0.0234(5) -0.0129(5) -0.0033(4) -0.0101(5) F2 0.0421(6) 0.0346(6) 0.0195(5) -0.0077(4) -0.0042(4) -0.0172(5) F6 0.0620(8) 0.0239(6) 0.0312(6) 0.0051(5) 0.0008(6) -0.0100(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C8 C13 1.397(2) . ? C8 C15 1.400(2) . ? C8 C10 1.506(2) . ? C10 O4 1.221(2) . ? C10 O5 1.298(2) . ? C11 O 1.238(2) . ? C11 N0AA 1.325(2) . ? C11 C12 1.515(2) . ? C12 C14 1.388(2) . ? C12 C16 1.396(2) . ? C13 F2 1.3451(18) . ? C13 C17 1.383(2) . ? C14 C19 1.377(2) . ? C14 H14 0.914(19) . ? C15 F1 1.3510(19) . ? C15 C18 1.377(2) . ? C16 C20 1.383(2) . ? C16 H16 0.97(2) . ? C17 C21 1.376(3) . ? C17 H17 0.98(2) . ? C18 C21 1.373(3) . ? C18 H18 0.92(2) . ? C19 N 1.348(2) . ? C19 H19 0.96(2) . ? C20 N 1.338(2) . ? C20 H20 0.94(2) . ? C21 F6 1.351(2) . ? N0AA H0AA 0.86(2) . ? N0AA H0AB 0.90(3) . ? O5 H5 0.8400 . ? 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 C13 C8 C15 114.49(15) . . ? C13 C8 C10 122.74(15) . . ? C15 C8 C10 122.76(15) . . ? O4 C10 O5 124.79(16) . . ? O4 C10 C8 122.62(15) . . ? O5 C10 C8 112.58(14) . . ? O C11 N0AA 123.77(16) . . ? O C11 C12 118.43(15) . . ? N0AA C11 C12 117.77(14) . . ? C14 C12 C16 118.68(15) . . ? C14 C12 C11 118.46(14) . . ? C16 C12 C11 122.78(15) . . ? F2 C13 C17 116.81(15) . . ? F2 C13 C8 118.79(15) . . ? C17 C13 C8 124.34(16) . . ? C19 C14 C12 119.28(16) . . ? C19 C14 H14 117.0(11) . . ? C12 C14 H14 123.7(11) . . ? F1 C15 C18 117.45(15) . . ? F1 C15 C8 118.50(15) . . ? C18 C15 C8 124.00(16) . . ? C20 C16 C12 118.43(16) . . ? C20 C16 H16 119.4(12) . . ? C12 C16 H16 122.2(12) . . ? C21 C17 C13 116.58(16) . . ? C21 C17 H17 123.5(13) . . ? C13 C17 H17 119.9(13) . . ? C21 C18 C15 117.15(16) . . ? C21 C18 H18 121.9(14) . . ? C15 C18 H18 120.9(14) . . ? N C19 C14 122.25(16) . . ? N C19 H19 115.6(12) . . ? C14 C19 H19 122.1(12) . . ? N C20 C16 122.90(15) . . ? N C20 H20 117.1(14) . . ? C16 C20 H20 119.9(14) . . ? F6 C21 C18 118.54(16) . . ? F6 C21 C17 118.02(16) . . ? C18 C21 C17 123.44(17) . . ? C11 N0AA H0AA 122.5(14) . . ? C11 N0AA H0AB 116.6(15) . . ? H0AA N0AA H0AB 120(2) . . ? C20 N C19 118.44(14) . . ? C10 O5 H5 109.5 . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.337 _refine_diff_density_min -0.348 _refine_diff_density_rms 0.058 _database_code_depnum_ccdc_archive 'CCDC 965664' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_shelx _audit_creation_method SHELXL-2013 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H18 F6 N4 O6' _chemical_formula_weight 596.44 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' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 3.8198(6) _cell_length_b 7.5011(9) _cell_length_c 21.814(3) _cell_angle_alpha 98.435(8) _cell_angle_beta 93.169(8) _cell_angle_gamma 97.474(7) _cell_volume 611.26(14) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.620 _exptl_crystal_F_000 304 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_min 0.050 _exptl_absorpt_coefficient_mu 0.146 _shelx_estimated_absorpt_T_min 0.958 _shelx_estimated_absorpt_T_max 0.993 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.958 _exptl_absorpt_correction_T_max 0.993 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source ? _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 7504 _diffrn_reflns_av_unetI/netI 0.0557 _diffrn_reflns_av_R_equivalents 0.0393 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.893 _diffrn_reflns_theta_max 26.998 _diffrn_reflns_theta_full 25.242 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_point_group_measured_fraction_full 0.998 _reflns_number_total 2662 _reflns_number_gt 1814 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; ? ; _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^)+(0.0759P)^2^] where P=(Fo^2^+2Fc^2^)/3 ; _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 2662 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0808 _refine_ls_R_factor_gt 0.0487 _refine_ls_wR_factor_ref 0.1288 _refine_ls_wR_factor_gt 0.1151 _refine_ls_goodness_of_fit_ref 0.963 _refine_ls_restrained_S_all 0.963 _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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group F1 F 0.6496(4) 0.86156(16) 0.30427(6) 0.0276(4) Uani 1 1 d . . . . . F2 F 0.4038(4) 0.27614(16) 0.35931(6) 0.0270(4) Uani 1 1 d . . . . . O1 O 0.8221(4) 0.3468(2) 0.26956(7) 0.0233(4) Uani 1 1 d . . . . . F3 F 0.2067(4) 0.78611(19) 0.49494(6) 0.0340(4) Uani 1 1 d . . . . . O2 O 0.5923(5) 0.5462(2) 0.21820(7) 0.0255(4) Uani 1 1 d . . . . . C1 C 0.5358(6) 0.5637(3) 0.32717(10) 0.0175(5) Uani 1 1 d . . . . . C3 C 0.4290(6) 0.8294(3) 0.39956(10) 0.0233(5) Uani 1 1 d . . . . . C2 C 0.5338(6) 0.7496(3) 0.34391(10) 0.0200(5) Uani 1 1 d . . . . . C5 C 0.3019(6) 0.5281(3) 0.42718(11) 0.0223(5) Uani 1 1 d . . . . . C7 C 0.6550(6) 0.4827(3) 0.26555(10) 0.0185(5) Uani 1 1 d . . . . . C6 C 0.4168(6) 0.4581(3) 0.37125(10) 0.0201(5) Uani 1 1 d . . . . . C4 C 0.3139(6) 0.7142(3) 0.43988(10) 0.0249(5) Uani 1 1 d . . . . . O3 O 0.6715(4) 0.28235(19) -0.00370(7) 0.0225(4) Uani 1 1 d . . . . . N1 N 0.9533(5) -0.1563(2) -0.18037(8) 0.0181(4) Uani 1 1 d . . . . . N2 N 0.5123(5) 0.4217(2) -0.08400(9) 0.0201(4) Uani 1 1 d . . . . . C13 C 0.6352(6) 0.2855(3) -0.06008(10) 0.0178(5) Uani 1 1 d . . . . . C9 C 0.7714(6) 0.1381(3) -0.16700(10) 0.0197(5) Uani 1 1 d . . . . . C10 C 0.7357(6) 0.1302(3) -0.10479(10) 0.0164(5) Uani 1 1 d . . . . . C11 C 0.8023(6) -0.0255(3) -0.08124(10) 0.0179(5) Uani 1 1 d . . . . . C8 C 0.8792(6) -0.0085(3) -0.20346(11) 0.0201(5) Uani 1 1 d . . . . . C12 C 0.9143(6) -0.1654(3) -0.12020(10) 0.0202(5) Uani 1 1 d . . . . . H11 H 0.767(6) -0.037(3) -0.0383(10) 0.014(6) Uiso 1 1 d . . . . . H3 H 0.434(7) 0.962(4) 0.4091(11) 0.033(7) Uiso 1 1 d . . . . . H8 H 0.916(6) -0.014(3) -0.2475(11) 0.019(6) Uiso 1 1 d . . . . . H9 H 0.734(6) 0.241(3) -0.1857(10) 0.022(6) Uiso 1 1 d . . . . . H5 H 0.219(7) 0.449(4) 0.4539(12) 0.038(8) Uiso 1 1 d . . . . . H2A H 0.447(7) 0.515(3) -0.0569(11) 0.026(7) Uiso 1 1 d . . . . . H12 H 0.979(7) -0.280(4) -0.1053(12) 0.035(7) Uiso 1 1 d . . . . . H1 H 0.928(8) 0.281(4) 0.2217(15) 0.058(9) Uiso 1 1 d . . . . . H2B H 0.476(9) 0.416(4) -0.1273(16) 0.061(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 F1 0.0420(9) 0.0132(6) 0.0281(7) 0.0051(5) 0.0081(6) 0.0017(6) F2 0.0389(9) 0.0133(6) 0.0306(8) 0.0073(5) 0.0055(6) 0.0042(6) O1 0.0314(10) 0.0164(8) 0.0230(8) -0.0001(6) 0.0013(7) 0.0108(7) F3 0.0426(9) 0.0345(8) 0.0232(8) -0.0047(6) 0.0102(6) 0.0059(7) O2 0.0377(11) 0.0212(8) 0.0200(8) 0.0049(6) 0.0040(7) 0.0105(7) C1 0.0184(12) 0.0146(10) 0.0195(11) 0.0026(8) 0.0006(9) 0.0030(9) C3 0.0273(13) 0.0165(11) 0.0239(12) -0.0034(9) -0.0008(10) 0.0038(9) C2 0.0252(13) 0.0154(11) 0.0191(11) 0.0041(8) 0.0012(9) 0.0010(9) C5 0.0247(13) 0.0223(12) 0.0204(12) 0.0065(9) 0.0015(10) 0.0017(9) C7 0.0209(12) 0.0124(10) 0.0210(11) 0.0006(8) -0.0007(9) 0.0011(9) C6 0.0219(12) 0.0137(10) 0.0239(12) 0.0024(9) -0.0025(9) 0.0018(9) C4 0.0266(13) 0.0294(13) 0.0170(11) -0.0037(9) 0.0039(10) 0.0055(10) O3 0.0346(10) 0.0160(8) 0.0180(8) 0.0026(6) 0.0028(7) 0.0068(7) N1 0.0210(10) 0.0100(8) 0.0225(10) 0.0005(7) 0.0020(8) 0.0019(7) N2 0.0269(11) 0.0129(9) 0.0206(11) -0.0003(8) 0.0023(8) 0.0063(8) C13 0.0193(12) 0.0124(10) 0.0208(11) 0.0013(8) 0.0036(9) 0.0001(8) C9 0.0229(12) 0.0141(10) 0.0223(12) 0.0040(9) 0.0014(9) 0.0030(9) C10 0.0161(11) 0.0127(10) 0.0191(11) 0.0002(8) 0.0009(9) -0.0001(8) C11 0.0197(12) 0.0144(10) 0.0187(11) 0.0033(8) -0.0004(9) -0.0012(9) C8 0.0233(12) 0.0167(11) 0.0206(12) 0.0030(9) 0.0043(9) 0.0032(9) C12 0.0248(13) 0.0127(11) 0.0230(12) 0.0029(9) 0.0010(10) 0.0022(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 C2 1.345(3) . ? F2 C6 1.346(2) . ? O1 C7 1.282(3) . ? O1 H1 1.20(3) . ? F3 C4 1.350(3) . ? O2 C7 1.224(2) . ? C1 C2 1.390(3) . ? C1 C6 1.391(3) . ? C1 C7 1.511(3) . ? C3 C4 1.371(3) . ? C3 C2 1.377(3) . ? C3 H3 0.98(3) . ? C5 C6 1.374(3) . ? C5 C4 1.377(3) . ? C5 H5 0.93(3) . ? O3 C13 1.234(3) . ? N1 C8 1.339(3) . ? N1 C12 1.340(3) . ? N2 C13 1.338(3) . ? N2 H2A 0.92(3) . ? N2 H2B 0.94(3) . ? C13 C10 1.510(3) . ? C9 C10 1.381(3) . ? C9 C8 1.381(3) . ? C9 H9 0.95(2) . ? C10 C11 1.390(3) . ? C11 C12 1.379(3) . ? C11 H11 0.97(2) . ? C8 H8 0.97(2) . ? C12 H12 1.02(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 C7 O1 H1 115.0(15) . . ? C2 C1 C6 114.8(2) . . ? C2 C1 C7 122.44(19) . . ? C6 C1 C7 122.72(19) . . ? C4 C3 C2 116.4(2) . . ? C4 C3 H3 122.4(15) . . ? C2 C3 H3 121.1(15) . . ? F1 C2 C3 116.87(19) . . ? F1 C2 C1 118.63(19) . . ? C3 C2 C1 124.5(2) . . ? C6 C5 C4 117.0(2) . . ? C6 C5 H5 119.3(16) . . ? C4 C5 H5 123.7(16) . . ? O2 C7 O1 126.0(2) . . ? O2 C7 C1 121.04(19) . . ? O1 C7 C1 112.93(18) . . ? F2 C6 C5 116.5(2) . . ? F2 C6 C1 119.63(19) . . ? C5 C6 C1 123.9(2) . . ? F3 C4 C3 118.6(2) . . ? F3 C4 C5 118.0(2) . . ? C3 C4 C5 123.4(2) . . ? C8 N1 C12 119.31(18) . . ? C13 N2 H2A 117.7(15) . . ? C13 N2 H2B 120.7(19) . . ? H2A N2 H2B 121(2) . . ? O3 C13 N2 123.1(2) . . ? O3 C13 C10 119.17(19) . . ? N2 C13 C10 117.75(19) . . ? C10 C9 C8 118.6(2) . . ? C10 C9 H9 123.3(14) . . ? C8 C9 H9 118.1(14) . . ? C9 C10 C11 119.2(2) . . ? C9 C10 C13 123.07(19) . . ? C11 C10 C13 117.76(19) . . ? C12 C11 C10 119.1(2) . . ? C12 C11 H11 120.2(13) . . ? C10 C11 H11 120.8(13) . . ? N1 C8 C9 122.3(2) . . ? N1 C8 H8 113.4(13) . . ? C9 C8 H8 124.3(13) . . ? N1 C12 C11 121.6(2) . . ? N1 C12 H12 115.6(15) . . ? C11 C12 H12 122.8(15) . . ? _refine_diff_density_max 0.247 _refine_diff_density_min -0.303 _refine_diff_density_rms 0.071 _shelxl_version_number 2013-2 _shelx_res_file ; TITL new_0, in P-1 #2 CELL 0.71073 3.8198 7.5011 21.8143 98.435 93.169 97.474 ZERR 1.00 0.0006 0.0009 0.0026 0.008 0.008 0.007 LATT 1 SFAC C H N O F UNIT 26 18 4 6 6 MERG 2 OMIT 0.00 54.00 FMAP 2 PLAN 10 SIZE 0.050 0.150 0.300 ACTA BOND $H L.S. 10 TEMP -173.00 WGHT 0.075900 FVAR 0.22953 F1 5 0.649572 0.861556 0.304266 11.00000 0.04198 0.01323 = 0.02811 0.00509 0.00806 0.00174 F2 5 0.403781 0.276140 0.359314 11.00000 0.03886 0.01332 = 0.03063 0.00733 0.00555 0.00424 O1 4 0.822087 0.346817 0.269556 11.00000 0.03144 0.01638 = 0.02302 -0.00013 0.00135 0.01079 F3 5 0.206740 0.786106 0.494938 11.00000 0.04256 0.03452 = 0.02316 -0.00467 0.01025 0.00591 O2 4 0.592322 0.546175 0.218198 11.00000 0.03774 0.02117 = 0.02001 0.00489 0.00400 0.01047 C1 1 0.535761 0.563651 0.327170 11.00000 0.01842 0.01455 = 0.01954 0.00257 0.00061 0.00301 C3 1 0.428983 0.829418 0.399564 11.00000 0.02729 0.01655 = 0.02386 -0.00340 -0.00082 0.00382 C2 1 0.533818 0.749558 0.343914 11.00000 0.02523 0.01539 = 0.01912 0.00409 0.00115 0.00095 C5 1 0.301858 0.528070 0.427181 11.00000 0.02473 0.02232 = 0.02039 0.00646 0.00150 0.00174 C7 1 0.654989 0.482708 0.265546 11.00000 0.02093 0.01238 = 0.02105 0.00063 -0.00067 0.00109 C6 1 0.416818 0.458132 0.371249 11.00000 0.02191 0.01374 = 0.02394 0.00235 -0.00247 0.00179 C4 1 0.313943 0.714228 0.439877 11.00000 0.02663 0.02937 = 0.01702 -0.00367 0.00394 0.00550 O3 4 0.671548 0.282354 -0.003703 11.00000 0.03457 0.01600 = 0.01800 0.00257 0.00285 0.00684 N1 3 0.953277 -0.156301 -0.180370 11.00000 0.02104 0.01004 = 0.02248 0.00054 0.00203 0.00186 N2 3 0.512305 0.421683 -0.083997 11.00000 0.02695 0.01287 = 0.02061 -0.00035 0.00234 0.00627 C13 1 0.635163 0.285487 -0.060076 11.00000 0.01935 0.01245 = 0.02083 0.00132 0.00365 0.00010 C9 1 0.771409 0.138070 -0.167002 11.00000 0.02289 0.01413 = 0.02235 0.00396 0.00136 0.00300 C10 1 0.735666 0.130173 -0.104788 11.00000 0.01612 0.01267 = 0.01912 0.00018 0.00089 -0.00010 C11 1 0.802288 -0.025522 -0.081238 11.00000 0.01972 0.01436 = 0.01872 0.00326 -0.00043 -0.00121 C8 1 0.879183 -0.008497 -0.203459 11.00000 0.02334 0.01668 = 0.02059 0.00299 0.00434 0.00315 C12 1 0.914316 -0.165434 -0.120200 11.00000 0.02481 0.01266 = 0.02296 0.00290 0.00097 0.00223 H11 2 0.767294 -0.037029 -0.038252 11.00000 0.01383 H3 2 0.433921 0.961967 0.409133 11.00000 0.03322 H8 2 0.916412 -0.013869 -0.247452 11.00000 0.01866 H9 2 0.733686 0.240560 -0.185746 11.00000 0.02192 H5 2 0.219111 0.449431 0.453893 11.00000 0.03781 H2A 2 0.446695 0.514578 -0.056923 11.00000 0.02554 H12 2 0.979211 -0.280185 -0.105278 11.00000 0.03537 H1 2 0.927867 0.280691 0.221664 11.00000 0.05765 H2B 2 0.476252 0.416299 -0.127334 11.00000 0.06081 HKLF 4 REM new_0, in P-1 #2 REM R1 = 0.0487 for 1814 Fo > 4sig(Fo) and 0.0808 for all 2662 data REM 226 parameters refined using 0 restraints END WGHT 0.0754 0.0000 REM Highest difference peak 0.247, deepest hole -0.303, 1-sigma level 0.071 Q1 1 0.5764 0.5286 0.3008 11.00000 0.05 0.25 Q2 1 0.6522 0.2008 -0.0885 11.00000 0.05 0.24 Q3 1 0.7197 0.3063 -0.2374 11.00000 0.05 0.24 Q4 1 1.3220 -0.0551 -0.2319 11.00000 0.05 0.22 Q5 1 0.8063 0.5015 -0.1013 11.00000 0.05 0.22 Q6 1 0.8203 0.2148 -0.2700 11.00000 0.05 0.22 Q7 1 1.1666 -0.0344 -0.2580 11.00000 0.05 0.21 Q8 1 1.0417 0.3690 -0.2015 11.00000 0.05 0.21 Q9 1 0.6980 0.8590 0.4483 11.00000 0.05 0.21 Q10 1 1.0639 0.2186 -0.1285 11.00000 0.05 0.21 ; _shelx_res_checksum 81080 _shelx_hkl_file ; -1 0 0 179.89 2.82 -2 0 0 3.42 0.49 -2 0 0 2.58 0.21 -2 0 0 3.46 0.24 -3 0 0 0.16 0.15 -3 0 0 0.02 0.42 -4 0 0 0.42 0.19 -4 0 0 -0.49 0.55 -4 1 0 0.18 0.17 -4 1 0 -0.15 0.50 -3 1 0 18.95 1.09 -3 1 0 18.90 0.51 -3 1 0 18.39 0.52 -2 1 0 16.61 0.92 -1 1 0 17.51 0.39 -1 1 0 17.99 0.74 -1 1 0 18.48 0.36 0 -1 0 19.22 0.45 0 -1 0 18.87 0.49 0 -1 0 18.84 0.41 0 -1 0 18.32 0.44 0 1 0 18.80 0.45 0 1 0 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-1 25 0.33 0.47 -2 -1 25 0.10 0.45 -2 -1 25 1.13 0.77 -1 -1 25 -0.31 0.44 -1 -1 25 0.12 0.39 0 -1 25 -0.29 0.38 0 -1 25 0.24 0.45 -1 1 -25 0.32 0.35 1 -1 25 0.19 0.47 -2 1 -25 -0.05 0.32 -2 1 -25 0.21 0.50 -3 0 25 0.74 0.49 -3 0 25 0.74 0.80 -2 0 25 0.18 0.74 -2 0 25 0.73 0.53 -1 0 25 3.02 0.72 0 0 25 -0.10 0.45 0 0 25 0.02 0.46 -1 0 -25 0.98 0.44 1 0 25 2.04 0.65 -2 0 -25 -0.10 0.53 -2 0 -25 0.04 0.35 -3 1 25 1.05 0.52 -3 1 25 1.12 0.99 -2 1 25 -0.04 0.45 -1 1 25 -0.24 0.45 -1 1 25 0.89 0.44 0 1 25 4.09 0.81 0 1 25 2.60 0.61 -1 -1 -25 0.19 0.32 1 1 25 0.50 0.59 -2 -1 -25 1.13 0.61 -2 -1 -25 1.45 0.45 -3 2 25 2.43 0.65 -2 2 25 0.88 0.54 -1 2 25 1.58 0.64 -1 2 25 1.27 0.43 0 2 25 0.82 0.59 0 2 25 0.95 0.63 -1 -2 -25 0.85 0.45 1 2 25 1.78 0.68 -2 -2 -25 -0.34 0.58 -2 -2 -25 0.00 0.40 -3 3 25 0.51 0.48 -2 3 25 1.08 0.60 -1 3 25 -0.21 0.37 -1 3 25 0.02 0.48 0 3 25 5.79 1.02 -1 -3 -25 0.77 0.45 1 3 25 0.57 0.58 2 -4 -25 2.08 0.59 -2 4 25 3.12 0.83 1 -4 -25 1.84 0.62 -1 4 25 0.35 0.62 0 4 25 0.07 0.56 0 4 25 0.03 0.53 -1 5 25 -0.07 0.56 0 5 25 0.89 0.75 0 -7 26 3.28 0.75 0 -7 26 1.48 0.63 0 -7 26 2.67 1.30 -1 7 -26 -0.01 0.41 -1 -6 26 2.79 0.70 -1 -6 26 4.04 1.27 0 -6 26 1.02 1.05 0 -6 26 2.04 0.69 0 -6 26 0.03 0.50 -1 6 -26 -0.24 0.35 -2 -5 26 -0.33 0.44 -2 -5 26 0.15 0.82 -1 -5 26 0.63 0.42 -1 -5 26 0.73 0.52 -1 -5 26 1.33 0.87 0 -5 26 -0.45 0.47 0 -5 26 -0.52 0.84 0 -5 26 0.34 0.49 -1 5 -26 0.13 0.39 -2 5 -26 0.76 0.46 -2 5 -26 0.25 0.58 -2 -4 26 -0.05 0.43 -2 -4 26 0.78 0.81 -1 -4 26 0.34 0.39 -1 -4 26 0.24 0.67 -1 -4 26 -0.02 0.46 0 -4 26 0.58 0.53 0 -4 26 1.26 0.61 0 -4 26 0.33 0.62 -1 4 -26 1.22 0.49 1 -4 26 0.16 0.56 -2 4 -26 0.35 0.45 -2 4 -26 0.66 0.60 -3 -3 26 -0.70 0.41 -2 -3 26 0.10 0.48 -2 -3 26 -0.41 0.79 -1 -3 26 0.84 0.69 -1 -3 26 0.56 0.39 -1 -3 26 1.54 0.63 0 -3 26 0.16 0.48 0 -3 26 0.01 0.46 -1 3 -26 0.21 0.37 1 -3 26 0.79 0.59 -2 3 -26 -0.05 0.54 -2 3 -26 0.87 0.46 -3 -2 26 -0.04 0.45 -3 -2 26 0.03 0.76 -2 -2 26 -0.52 0.41 -2 -2 26 -0.31 0.62 -1 -2 26 0.95 0.55 -1 -2 26 0.64 0.37 0 -2 26 -0.17 0.47 0 -2 26 0.18 0.52 -1 2 -26 -0.25 0.33 1 -2 26 -0.16 0.49 -2 2 -26 3.65 0.77 -3 -1 26 -0.23 0.97 -3 -1 26 0.15 0.53 -2 -1 26 3.01 0.74 -2 -1 26 3.06 0.93 -1 -1 26 0.70 0.44 -1 -1 26 0.43 0.58 0 -1 26 0.61 0.50 0 -1 26 0.38 0.50 -1 1 -26 0.52 0.40 1 -1 26 0.43 0.55 -2 1 -26 0.42 0.42 -2 1 -26 0.64 0.56 -3 0 26 0.05 0.89 -3 0 26 0.59 0.49 -2 0 26 7.48 0.96 -1 0 26 3.79 0.58 -1 0 26 7.65 1.09 0 0 26 0.41 0.53 0 0 26 0.42 0.51 -1 0 -26 0.52 0.37 1 0 26 -0.25 0.50 -2 0 -26 -0.20 0.33 -2 0 -26 0.59 0.60 -3 1 26 -0.21 0.44 -2 1 26 1.21 0.60 -1 1 26 0.35 0.53 -1 1 26 0.27 0.41 0 1 26 0.34 0.54 0 1 26 0.37 0.53 -1 -1 -26 -0.05 0.32 1 1 26 0.12 0.55 -2 -1 -26 0.05 0.36 -2 -1 -26 0.06 0.58 -3 2 26 3.43 0.79 -2 2 26 0.14 0.49 -1 2 26 7.40 1.09 0 2 26 0.77 0.63 0 2 26 0.60 0.60 -1 -2 -26 1.14 0.44 1 2 26 2.92 0.79 -2 -2 -26 0.73 0.44 -2 3 26 6.24 0.96 -1 3 26 -0.15 0.50 -1 3 26 -0.34 0.33 0 3 26 1.13 0.63 0 3 26 1.11 0.66 2 -4 -26 2.58 0.68 -2 4 26 3.68 0.92 1 -4 -26 2.23 0.67 -1 4 26 3.16 0.93 0 4 26 -0.21 0.63 0 4 26 -0.21 0.59 -1 -6 27 0.51 0.94 -1 -6 27 -0.20 0.51 0 -6 27 -0.35 0.95 0 -6 27 -0.51 0.46 0 -6 27 0.00 0.52 -1 6 -27 0.45 0.49 -2 -5 27 0.19 0.50 -1 -5 27 1.12 0.52 -1 -5 27 1.08 0.46 -1 -5 27 2.23 0.93 0 -5 27 0.84 0.63 0 -5 27 1.46 0.99 0 -5 27 0.45 0.51 -1 5 -27 1.83 0.57 -2 5 -27 -0.14 0.39 -2 -4 27 0.37 0.89 -2 -4 27 0.89 0.58 -1 -4 27 6.60 1.22 -1 -4 27 4.51 0.79 -1 -4 27 3.57 0.59 0 -4 27 -0.02 0.51 0 -4 27 -0.02 0.54 -1 4 -27 2.21 0.57 1 -4 27 2.87 0.79 -2 4 -27 1.05 0.52 -2 4 -27 0.42 0.58 -2 -3 27 1.52 0.93 -2 -3 27 1.23 0.65 -1 -3 27 0.19 0.37 -1 -3 27 0.79 0.73 -1 -3 27 0.94 0.57 0 -3 27 0.01 0.50 0 -3 27 0.76 0.57 -1 3 -27 0.58 0.44 1 -3 27 0.13 0.51 -2 3 -27 1.63 0.67 -2 3 -27 1.45 0.53 -2 -2 27 1.06 0.79 -1 -2 27 -0.13 0.47 -1 -2 27 0.13 0.35 0 -2 27 0.12 0.47 0 -2 27 -0.09 0.51 -1 2 -27 1.44 0.49 1 -2 27 0.99 0.57 -2 2 -27 1.87 0.52 -2 2 -27 1.68 0.71 -3 -1 27 -0.10 0.49 -2 -1 27 0.04 0.57 -1 -1 27 0.85 0.58 -1 -1 27 0.30 0.39 0 -1 27 0.86 0.61 0 -1 27 0.40 0.50 -1 1 -27 1.31 0.51 1 -1 27 0.15 0.52 -2 1 -27 1.63 0.55 -2 1 -27 0.23 0.61 -3 0 27 0.35 0.50 -2 0 27 6.54 0.97 -1 0 27 4.48 0.83 -1 0 27 3.39 0.58 0 0 27 0.17 0.54 0 0 27 -0.19 0.53 -1 0 -27 -0.21 0.39 1 0 27 0.13 0.58 -2 0 -27 -0.05 0.42 -2 0 -27 0.03 0.60 -2 1 27 2.45 0.74 -1 1 27 0.63 0.43 -1 1 27 0.74 0.64 0 1 27 0.09 0.57 0 1 27 1.25 0.66 -1 -1 -27 -0.09 0.36 1 1 27 -0.14 0.52 -2 -1 -27 0.74 0.61 -2 -1 -27 0.09 0.40 -2 2 27 -0.27 0.49 -1 2 27 -0.53 0.55 0 2 27 0.91 0.63 0 2 27 0.25 0.55 1 2 27 2.72 0.86 -2 3 27 6.71 1.01 -1 3 27 1.12 0.67 0 3 27 5.18 1.05 0 3 27 1.35 0.69 -1 4 27 2.73 0.92 0 -6 28 -0.46 0.54 0 -6 28 -0.05 0.57 0 -6 28 -0.36 0.91 -1 -5 28 -0.33 0.44 -1 -5 28 1.13 0.98 -1 -5 28 0.13 0.46 0 -5 28 0.50 0.62 0 -5 28 -0.29 0.47 -1 5 -28 0.22 0.44 -2 -4 28 -0.15 0.87 -2 -4 28 0.18 0.52 -1 -4 28 1.71 0.49 -1 -4 28 4.94 0.88 -1 -4 28 3.11 0.92 0 -4 28 0.45 0.60 -1 4 -28 1.03 0.52 -2 -3 28 4.59 1.22 -2 -3 28 3.73 0.84 -1 -3 28 0.51 0.42 0 -3 28 1.08 0.65 0 -3 28 0.93 0.60 -1 3 -28 0.40 0.40 1 -3 28 0.78 0.57 -2 3 -28 0.20 0.60 -2 3 -28 -0.08 0.41 -2 -2 28 -0.30 0.46 -1 -2 28 0.09 0.55 -1 -2 28 -0.05 0.38 0 -2 28 -0.02 0.51 0 -2 28 1.74 0.70 -1 2 -28 -0.03 0.38 1 -2 28 -0.14 0.48 -2 2 -28 -0.24 0.38 -2 2 -28 -0.09 0.58 -2 -1 28 1.75 0.70 -1 -1 28 1.96 0.70 0 -1 28 1.05 0.56 0 -1 28 0.15 0.51 -1 1 -28 0.01 0.39 1 -1 28 0.44 0.64 -2 1 -28 -0.12 0.40 -2 1 -28 -0.84 0.56 -2 0 28 1.14 0.63 -1 0 28 1.17 0.60 -1 0 28 0.08 0.42 0 0 28 0.01 0.52 0 0 28 -0.19 0.56 -1 0 -28 0.06 0.39 1 0 28 -0.20 0.52 -2 1 28 0.15 0.51 -1 1 28 0.77 0.45 -1 1 28 1.34 0.76 0 1 28 -0.48 0.52 0 1 28 0.21 0.58 1 1 28 -0.10 0.55 -2 2 28 3.10 0.82 -1 2 28 3.96 0.97 0 2 28 2.51 0.77 0 2 28 2.18 0.75 -1 3 28 0.18 0.66 0 3 28 0.59 0.62 0 3 28 1.05 0.83 -1 -5 29 -0.14 0.52 0 -5 29 5.58 0.92 0 -5 29 2.48 0.66 -1 -4 29 0.50 0.58 -1 -4 29 0.36 0.44 0 -4 29 0.36 0.61 0 -4 29 0.09 0.58 -2 -3 29 0.09 0.94 -2 -3 29 0.41 0.58 -1 -3 29 0.61 0.40 0 -3 29 -0.31 0.54 0 -3 29 -0.10 0.57 -1 3 -29 0.67 0.50 -2 -2 29 -0.59 0.55 -1 -2 29 0.76 0.69 0 -2 29 1.16 0.64 0 -2 29 0.42 0.53 -1 2 -29 0.36 0.42 1 -2 29 0.80 0.68 -2 -1 29 -0.23 0.52 -1 -1 29 -0.15 0.50 0 -1 29 5.27 0.95 0 -1 29 2.09 0.72 1 -1 29 4.40 0.96 -2 0 29 0.72 0.60 -1 0 29 3.31 0.84 0 0 29 -0.59 0.60 0 0 29 -0.10 0.51 -2 1 29 0.80 0.63 -1 1 29 0.65 0.73 0 1 29 0.48 0.61 0 1 29 0.36 0.61 -1 2 29 3.18 0.96 0 2 29 3.85 0.93 -1 -4 30 0.54 0.56 0 -4 30 0.76 0.65 0 -4 30 0.69 0.68 -1 -3 30 -0.44 0.55 0 -3 30 0.71 0.68 0 -3 30 0.11 0.58 -1 -2 30 4.73 0.94 0 -2 30 1.09 0.63 0 -2 30 2.60 0.76 -1 -1 30 6.68 1.16 0 -1 30 -0.47 0.51 0 -1 30 0.70 0.65 -1 0 30 1.21 0.70 0 0 30 1.80 0.67 0 0 30 3.95 0.99 -1 1 30 6.48 1.14 0 1 30 0.79 0.77 0 1 30 -0.34 0.56 0 -3 31 0.04 0.65 -1 -2 31 1.33 0.73 0 -2 31 10.70 1.40 -1 -1 31 0.46 0.62 0 -1 31 1.18 0.77 0 -1 31 0.11 0.61 0 0 0 0.00 0.00 ; _shelx_hkl_checksum 60326 _database_code_depnum_ccdc_archive 'CCDC 965665' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_datam _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H9 F2 N2 O3' _chemical_formula_weight 279.22 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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.0231(8) _cell_length_b 7.4789(9) _cell_length_c 12.6456(15) _cell_angle_alpha 74.419(5) _cell_angle_beta 87.775(6) _cell_angle_gamma 70.545(5) _cell_volume 602.33(12) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.540 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 286 _exptl_absorpt_coefficient_mu 0.131 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9743 _exptl_absorpt_correction_T_max 0.9870 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6013 _diffrn_reflns_av_R_equivalents 0.0229 _diffrn_reflns_av_sigmaI/netI 0.0280 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2762 _reflns_number_gt 2340 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0575P)^2^+0.1943P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2762 _refine_ls_number_parameters 224 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0525 _refine_ls_R_factor_gt 0.0439 _refine_ls_wR_factor_ref 0.1170 _refine_ls_wR_factor_gt 0.1112 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _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 0.3573(2) 0.1372(2) 0.18768(11) 0.0228(3) Uani 1 1 d . . . C2 C 0.2883(2) 0.3428(2) 0.11339(11) 0.0244(3) Uani 1 1 d . . . C3 C 0.3834(2) -0.0234(2) 0.14498(12) 0.0261(3) Uani 1 1 d . . . C4 C 0.3964(2) 0.0955(2) 0.30048(12) 0.0265(3) Uani 1 1 d . . . C5 C 0.4567(2) -0.0942(2) 0.36936(13) 0.0320(3) Uani 1 1 d . . . C6 C 0.4442(2) -0.2156(2) 0.21155(13) 0.0302(3) Uani 1 1 d . . . C7 C 0.4791(2) -0.2449(2) 0.32221(13) 0.0315(3) Uani 1 1 d . . . O1 O 0.22561(18) 0.49000(15) 0.14603(9) 0.0335(3) Uani 1 1 d . . . O2 O 0.3012(2) 0.34692(16) 0.00934(9) 0.0401(3) Uani 1 1 d . . . H2 H 0.2591 0.4644 -0.0293 0.060 Uiso 1 1 calc R . . F1 F 0.38415(18) 0.23799(15) 0.34643(8) 0.0329(3) Uani 0.795(3) 1 d P . . F2 F 0.54137(17) -0.43173(14) 0.38777(8) 0.0469(3) Uani 1 1 d . . . F3 F 0.3389(8) -0.0027(7) 0.0515(4) 0.0388(14) Uani 0.205(3) 1 d P . . H1A H -0.095(3) 0.416(3) 0.7160(17) 0.043(5) Uiso 1 1 d . . . H1B H -0.077(3) 0.522(3) 0.5944(17) 0.045(5) Uiso 1 1 d . . . H5 H 0.482(3) -0.120(3) 0.4457(16) 0.042(5) Uiso 1 1 d . . . H6 H 0.461(3) -0.325(3) 0.1794(15) 0.038(5) Uiso 1 1 d . . . H10 H 0.083(3) 0.162(3) 0.8476(14) 0.030(4) Uiso 1 1 d . . . H11 H 0.090(3) -0.123(2) 0.6076(15) 0.034(5) Uiso 1 1 d . . . H12 H 0.179(3) -0.416(3) 0.7467(14) 0.036(5) Uiso 1 1 d . . . C9 C 0.0334(2) 0.2432(2) 0.62126(11) 0.0236(3) Uani 1 1 d . . . C10 C 0.1009(2) 0.0436(2) 0.82318(12) 0.0254(3) Uani 1 1 d . . . C11 C 0.1065(2) -0.1187(2) 0.68303(12) 0.0253(3) Uani 1 1 d . . . C12 C 0.1568(2) -0.2948(2) 0.76465(12) 0.0281(3) Uani 1 1 d . . . C13 C 0.0781(2) 0.05446(19) 0.71236(11) 0.0217(3) Uani 1 1 d . . . C14 C 0.1527(2) -0.1394(2) 0.89941(12) 0.0273(3) Uani 1 1 d . . . N1 N -0.0484(2) 0.41204(18) 0.64808(11) 0.0299(3) Uani 1 1 d . . . N2 N 0.18121(19) -0.30637(17) 0.87111(10) 0.0271(3) Uani 1 1 d . . . O3 O 0.07805(17) 0.23397(15) 0.52709(8) 0.0320(3) Uani 1 1 d . . . H14 H 0.170(3) -0.155(2) 0.9812(14) 0.030(4) 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 0.0220(6) 0.0229(7) 0.0221(7) -0.0043(5) 0.0017(5) -0.0072(5) C2 0.0260(7) 0.0235(7) 0.0228(7) -0.0048(5) 0.0018(5) -0.0082(6) C3 0.0279(7) 0.0258(7) 0.0254(7) -0.0066(6) 0.0008(5) -0.0102(6) C4 0.0264(7) 0.0281(7) 0.0235(7) -0.0076(6) 0.0016(5) -0.0071(6) C5 0.0322(8) 0.0358(8) 0.0211(7) -0.0016(6) -0.0005(6) -0.0071(7) C6 0.0323(8) 0.0231(7) 0.0354(8) -0.0063(6) 0.0010(6) -0.0109(6) C7 0.0289(7) 0.0244(7) 0.0329(8) 0.0034(6) 0.0020(6) -0.0074(6) O1 0.0474(7) 0.0226(5) 0.0294(6) -0.0085(4) 0.0040(5) -0.0093(5) O2 0.0657(8) 0.0225(5) 0.0205(5) -0.0016(4) 0.0038(5) -0.0034(5) F1 0.0454(7) 0.0273(6) 0.0227(6) -0.0130(4) -0.0027(5) -0.0027(5) F2 0.0580(7) 0.0271(5) 0.0397(6) 0.0085(4) 0.0010(5) -0.0077(5) F3 0.057(3) 0.034(2) 0.026(2) -0.0077(18) 0.005(2) -0.016(2) C9 0.0263(7) 0.0208(6) 0.0215(7) -0.0027(5) 0.0008(5) -0.0073(5) C10 0.0286(7) 0.0227(7) 0.0244(7) -0.0059(5) 0.0015(5) -0.0083(6) C11 0.0295(7) 0.0216(7) 0.0227(7) -0.0046(5) 0.0002(5) -0.0067(6) C12 0.0320(8) 0.0206(7) 0.0292(8) -0.0052(6) 0.0029(6) -0.0067(6) C13 0.0213(6) 0.0200(6) 0.0212(6) -0.0028(5) 0.0018(5) -0.0060(5) C14 0.0304(7) 0.0280(7) 0.0210(7) -0.0029(5) 0.0003(5) -0.0095(6) N1 0.0432(8) 0.0182(6) 0.0229(6) -0.0025(5) 0.0061(5) -0.0062(5) N2 0.0289(6) 0.0226(6) 0.0247(6) -0.0009(5) 0.0011(5) -0.0063(5) O3 0.0478(7) 0.0232(5) 0.0209(5) -0.0038(4) 0.0049(4) -0.0086(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C4 1.3934(19) . ? C1 C3 1.4008(19) . ? C1 C2 1.4981(18) . ? C2 O1 1.2181(17) . ? C2 O2 1.3081(17) . ? C3 F3 1.191(5) . ? C3 C6 1.388(2) . ? C4 F1 1.3224(17) . ? C4 C5 1.384(2) . ? C5 C7 1.373(2) . ? C5 H5 0.944(19) . ? C6 C7 1.376(2) . ? C6 H6 0.979(19) . ? C7 F2 1.3527(17) . ? O2 H2 0.8400 . ? C9 O3 1.2338(17) . ? C9 N1 1.3306(18) . ? C9 C13 1.5094(18) . ? C10 C14 1.3861(19) . ? C10 C13 1.3942(19) . ? C10 H10 0.981(17) . ? C11 C12 1.3831(19) . ? C11 C13 1.3910(19) . ? C11 H11 0.975(18) . ? C12 N2 1.3398(19) . ? C12 H12 0.956(19) . ? C14 N2 1.3400(19) . ? C14 H14 1.016(17) . ? N1 H1A 0.91(2) . ? N1 H1B 0.88(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 C4 C1 C3 116.95(13) . . ? C4 C1 C2 122.80(13) . . ? C3 C1 C2 120.25(12) . . ? O1 C2 O2 123.60(13) . . ? O1 C2 C1 123.84(13) . . ? O2 C2 C1 112.55(12) . . ? F3 C3 C6 115.7(3) . . ? F3 C3 C1 122.1(2) . . ? C6 C3 C1 121.84(13) . . ? F1 C4 C5 116.50(13) . . ? F1 C4 C1 120.68(13) . . ? C5 C4 C1 122.77(14) . . ? C7 C5 C4 117.30(14) . . ? C7 C5 H5 121.1(12) . . ? C4 C5 H5 121.6(12) . . ? C7 C6 C3 117.80(14) . . ? C7 C6 H6 122.2(11) . . ? C3 C6 H6 120.0(11) . . ? F2 C7 C5 118.26(14) . . ? F2 C7 C6 118.40(14) . . ? C5 C7 C6 123.33(14) . . ? C2 O2 H2 109.5 . . ? O3 C9 N1 123.49(13) . . ? O3 C9 C13 118.91(12) . . ? N1 C9 C13 117.57(12) . . ? C14 C10 C13 118.67(13) . . ? C14 C10 H10 120.0(10) . . ? C13 C10 H10 121.4(10) . . ? C12 C11 C13 118.87(13) . . ? C12 C11 H11 117.7(10) . . ? C13 C11 H11 123.4(10) . . ? N2 C12 C11 122.78(13) . . ? N2 C12 H12 116.6(11) . . ? C11 C12 H12 120.6(11) . . ? C11 C13 C10 118.58(12) . . ? C11 C13 C9 117.80(12) . . ? C10 C13 C9 123.56(12) . . ? N2 C14 C10 122.75(13) . . ? N2 C14 H14 115.4(9) . . ? C10 C14 H14 121.9(10) . . ? C9 N1 H1A 122.0(12) . . ? C9 N1 H1B 117.4(13) . . ? H1A N1 H1B 119.7(18) . . ? C12 N2 C14 118.33(12) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.286 _refine_diff_density_min -0.235 _refine_diff_density_rms 0.045 _database_code_depnum_ccdc_archive 'CCDC 965666' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_shelx _audit_creation_method SHELXL-2013 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H8 F2 N2 O3' _chemical_formula_weight 278.21 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' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.3252(6) _cell_length_b 12.1896(9) _cell_length_c 13.4770(10) _cell_angle_alpha 107.408(8) _cell_angle_beta 102.834(7) _cell_angle_gamma 94.816(7) _cell_volume 1255.68(17) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.472 _exptl_crystal_F_000 568 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.150 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.100 _exptl_absorpt_coefficient_mu 0.126 _shelx_estimated_absorpt_T_min 0.981 _shelx_estimated_absorpt_T_max 0.988 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source ? _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 13487 _diffrn_reflns_av_unetI/netI 0.0414 _diffrn_reflns_av_R_equivalents 0.0324 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.113 _diffrn_reflns_theta_max 27.477 _diffrn_reflns_theta_full 25.242 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_point_group_measured_fraction_full 0.998 _reflns_number_total 5746 _reflns_number_gt 4106 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; ? ; _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^)+(0.0795P)^2^+0.4629P] where P=(Fo^2^+2Fc^2^)/3 ; _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 5746 _refine_ls_number_parameters 445 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0782 _refine_ls_R_factor_gt 0.0532 _refine_ls_wR_factor_ref 0.1566 _refine_ls_wR_factor_gt 0.1401 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C23 C 0.1587(2) -0.03695(17) 0.77508(16) 0.0206(4) Uani 1 1 d . . . . . C22 C 0.1308(3) 0.06003(19) 0.74407(17) 0.0245(4) Uani 1 1 d . . . . . C14 C 0.5070(2) 0.98252(17) 0.67055(15) 0.0197(4) Uani 1 1 d . . . . . C24 C 0.0575(3) -0.14321(18) 0.71412(17) 0.0231(4) Uani 1 1 d . . . . . C19 C 0.6176(3) 1.08738(18) 0.72185(17) 0.0252(5) Uani 1 1 d . . . . . C10 C 0.6463(2) 0.45802(17) 0.60373(16) 0.0223(4) Uani 1 1 d . . . . . C16 C 0.6623(3) 0.90352(19) 0.80155(18) 0.0278(5) Uani 1 1 d . . . . . C20 C 0.3653(2) 0.97007(17) 0.57439(16) 0.0198(4) Uani 1 1 d . . . . . C26 C 0.2983(2) -0.02005(17) 0.87446(16) 0.0207(4) Uani 1 1 d . . . . . C7 C 0.0957(3) 0.56151(18) 0.81708(17) 0.0241(4) Uani 1 1 d . . . . . C21 C 0.0015(3) 0.04872(19) 0.65521(18) 0.0258(5) Uani 1 1 d . . . . . C15 C 0.5341(3) 0.89245(17) 0.71233(17) 0.0229(4) Uani 1 1 d . . . . . C17 C 0.7713(3) 1.0077(2) 0.85167(17) 0.0291(5) Uani 1 1 d . . . . . C11 C 0.5603(3) 0.35220(18) 0.59544(18) 0.0266(5) Uani 1 1 d . . . . . C9 C 0.5921(3) 0.55877(19) 0.65640(18) 0.0275(5) Uani 1 1 d . . . . . C1 C -0.0474(3) 0.57076(18) 0.86808(16) 0.0233(4) Uani 1 1 d . . . . . C6 C -0.0940(3) 0.67697(18) 0.91579(17) 0.0254(5) Uani 1 1 d . . . . . C2 C -0.1391(3) 0.4706(2) 0.8694(2) 0.0309(5) Uani 1 1 d . . . . . C13 C 0.7967(3) 0.47358(18) 0.56048(17) 0.0248(4) Uani 1 1 d . . . . . C8 C 0.4563(3) 0.54978(19) 0.69809(19) 0.0288(5) Uani 1 1 d . . . . . C18 C 0.7455(3) 1.09692(19) 0.81001(18) 0.0295(5) Uani 1 1 d . . . . . C25 C -0.0692(3) -0.14685(19) 0.62648(17) 0.0238(4) Uani 1 1 d . . . . . C4 C -0.3129(3) 0.5862(2) 0.9653(2) 0.0401(6) Uani 1 1 d . . . . . C12 C 0.4251(3) 0.35091(19) 0.63947(19) 0.0289(5) Uani 1 1 d . . . . . C5 C -0.2239(3) 0.6857(2) 0.96453(19) 0.0321(5) Uani 1 1 d . . . . . C3 C -0.2696(3) 0.4803(2) 0.9167(2) 0.0402(6) Uani 1 1 d . . . . . N3 N -0.0973(2) -0.05282(15) 0.59787(14) 0.0245(4) Uani 1 1 d . . . . . N4 N 0.3250(2) -0.11220(16) 0.90464(16) 0.0251(4) Uani 1 1 d . . . . . N1 N 0.3735(2) 0.44800(15) 0.69060(15) 0.0275(4) Uani 1 1 d . . . . . N2 N 0.8483(2) 0.37809(16) 0.50764(16) 0.0293(4) Uani 1 1 d . . . . . O5 O 0.27332(18) 0.87785(12) 0.52204(12) 0.0255(3) Uani 1 1 d . . . . . O6 O 0.38083(19) 0.07814(12) 0.92268(12) 0.0296(4) Uani 1 1 d . . . . . O2 O 0.1817(2) 0.64487(13) 0.81349(14) 0.0340(4) Uani 1 1 d . . . . . O4 O 0.35073(18) 1.06756(12) 0.55425(12) 0.0258(3) Uani 1 1 d . . . . . O1 O 0.1187(2) 0.45382(13) 0.77633(14) 0.0359(4) Uani 1 1 d . . . . . O3 O 0.8647(2) 0.57263(13) 0.57522(15) 0.0383(4) Uani 1 1 d . . . . . F1 F -0.01234(17) 0.77761(11) 0.91592(11) 0.0360(3) Uani 1 1 d . . . . . F3A F 0.43158(18) 0.78990(11) 0.66875(12) 0.0300(5) Uani 0.854(4) 1 d . . P . . F3B F 0.6135(14) 1.1727(9) 0.7012(8) 0.051(4) Uani 0.146(4) 1 d . . P . . F4A F 0.85417(19) 1.19867(13) 0.85422(13) 0.0377(5) Uani 0.857(4) 1 d . . P . . F4B F 0.6607(14) 0.8123(10) 0.8283(8) 0.053(4) Uani 0.143(4) 1 d . . P . . F2 F -0.3588(2) 0.38181(14) 0.91626(18) 0.0703(6) Uani 1 1 d . . . . . H24 H 0.071(3) -0.213(2) 0.7287(18) 0.026(6) Uiso 1 1 d . . . . . H25 H -0.139(3) -0.216(2) 0.584(2) 0.030(6) Uiso 1 1 d . . . . . H22 H 0.199(3) 0.132(2) 0.785(2) 0.035(7) Uiso 1 1 d . . . . . H2 H -0.117(3) 0.394(2) 0.833(2) 0.046(8) Uiso 1 1 d . . . . . H12 H 0.361(3) 0.273(2) 0.634(2) 0.043(7) Uiso 1 1 d . . . . . H21 H -0.024(3) 0.118(2) 0.630(2) 0.039(7) Uiso 1 1 d . . . . . H5 H -0.248(3) 0.761(2) 1.000(2) 0.038(7) Uiso 1 1 d . . . . . H9 H 0.644(3) 0.637(2) 0.665(2) 0.038(7) Uiso 1 1 d . . . . . H11 H 0.593(3) 0.280(2) 0.562(2) 0.042(7) Uiso 1 1 d . . . . . H4 H -0.408(4) 0.592(2) 0.997(2) 0.051(8) Uiso 1 1 d . . . . . H8 H 0.419(3) 0.621(2) 0.735(2) 0.041(7) Uiso 1 1 d . . . . . H1 H 0.212(4) 0.455(3) 0.750(3) 0.074(11) Uiso 1 1 d . . . . . H4A H 0.403(3) -0.101(2) 0.958(2) 0.033(7) Uiso 1 1 d . . . . . H2A H 0.945(4) 0.392(2) 0.483(2) 0.044(8) Uiso 1 1 d . . . . . H4B H 0.262(4) -0.187(3) 0.868(2) 0.047(8) Uiso 1 1 d . . . . . H2B H 0.800(4) 0.305(3) 0.501(2) 0.047(8) 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 C23 0.0178(10) 0.0237(10) 0.0211(10) 0.0070(8) 0.0061(8) 0.0060(8) C22 0.0223(11) 0.0226(11) 0.0267(11) 0.0080(9) 0.0032(8) 0.0019(8) C14 0.0193(10) 0.0195(10) 0.0202(10) 0.0058(8) 0.0055(8) 0.0047(7) C24 0.0216(10) 0.0223(10) 0.0255(11) 0.0078(9) 0.0057(8) 0.0047(8) C19 0.0235(11) 0.0225(11) 0.0283(11) 0.0081(9) 0.0046(9) 0.0025(8) C10 0.0231(10) 0.0215(10) 0.0221(10) 0.0071(8) 0.0056(8) 0.0035(8) C16 0.0310(12) 0.0292(12) 0.0286(11) 0.0144(10) 0.0089(9) 0.0119(9) C20 0.0209(10) 0.0183(10) 0.0202(10) 0.0049(8) 0.0067(8) 0.0049(7) C26 0.0179(10) 0.0210(10) 0.0213(10) 0.0041(8) 0.0049(8) 0.0038(8) C7 0.0248(11) 0.0219(10) 0.0253(11) 0.0069(9) 0.0070(8) 0.0043(8) C21 0.0248(11) 0.0244(11) 0.0282(11) 0.0104(9) 0.0040(9) 0.0047(8) C15 0.0227(10) 0.0207(10) 0.0266(11) 0.0082(9) 0.0078(8) 0.0051(8) C17 0.0258(11) 0.0354(12) 0.0252(11) 0.0089(10) 0.0043(9) 0.0098(9) C11 0.0292(12) 0.0180(10) 0.0308(12) 0.0040(9) 0.0097(9) 0.0034(8) C9 0.0313(12) 0.0193(10) 0.0333(12) 0.0070(9) 0.0134(9) 0.0043(9) C1 0.0223(10) 0.0254(11) 0.0229(10) 0.0094(9) 0.0050(8) 0.0037(8) C6 0.0260(11) 0.0227(11) 0.0263(11) 0.0069(9) 0.0071(9) 0.0012(8) C2 0.0318(12) 0.0274(12) 0.0391(13) 0.0128(10) 0.0169(10) 0.0060(9) C13 0.0237(11) 0.0222(11) 0.0269(11) 0.0060(9) 0.0068(8) 0.0012(8) C8 0.0341(12) 0.0199(11) 0.0365(13) 0.0089(10) 0.0167(10) 0.0076(9) C18 0.0222(11) 0.0279(11) 0.0317(12) 0.0045(10) 0.0022(9) 0.0009(8) C25 0.0217(10) 0.0237(11) 0.0232(11) 0.0065(9) 0.0029(8) 0.0016(8) C4 0.0370(14) 0.0437(15) 0.0485(16) 0.0151(13) 0.0274(12) 0.0102(11) C12 0.0309(12) 0.0198(11) 0.0352(12) 0.0049(9) 0.0137(10) 0.0012(9) C5 0.0319(12) 0.0327(13) 0.0315(12) 0.0070(10) 0.0120(10) 0.0081(10) C3 0.0397(14) 0.0332(13) 0.0572(17) 0.0188(12) 0.0275(13) 0.0027(11) N3 0.0222(9) 0.0259(9) 0.0253(9) 0.0094(8) 0.0041(7) 0.0052(7) N4 0.0211(9) 0.0248(10) 0.0253(10) 0.0084(8) -0.0018(8) 0.0018(7) N1 0.0297(10) 0.0208(9) 0.0353(11) 0.0093(8) 0.0144(8) 0.0051(7) N2 0.0273(10) 0.0209(9) 0.0388(11) 0.0036(8) 0.0161(9) 0.0022(8) O5 0.0239(8) 0.0198(7) 0.0274(8) 0.0051(6) 0.0006(6) 0.0012(6) O6 0.0290(8) 0.0215(8) 0.0298(8) 0.0047(7) -0.0037(6) 0.0027(6) O2 0.0340(9) 0.0237(8) 0.0494(10) 0.0114(7) 0.0226(8) 0.0033(6) O4 0.0286(8) 0.0180(7) 0.0282(8) 0.0096(6) -0.0001(6) 0.0019(6) O1 0.0400(10) 0.0229(8) 0.0527(11) 0.0099(8) 0.0302(9) 0.0069(7) O3 0.0397(10) 0.0209(8) 0.0565(11) 0.0060(8) 0.0276(8) 0.0001(7) F1 0.0390(8) 0.0236(7) 0.0462(8) 0.0069(6) 0.0196(6) 0.0033(5) F3A 0.0339(9) 0.0160(7) 0.0360(9) 0.0122(6) -0.0021(6) -0.0007(6) F3B 0.058(7) 0.049(7) 0.043(6) 0.029(5) -0.005(5) 0.000(5) F4A 0.0323(9) 0.0279(9) 0.0380(10) 0.0074(7) -0.0107(7) -0.0085(6) F4B 0.048(7) 0.066(8) 0.038(6) 0.013(6) -0.003(5) 0.025(6) F2 0.0691(12) 0.0416(9) 0.1263(17) 0.0327(10) 0.0709(12) 0.0068(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 C23 C22 1.387(3) . ? C23 C24 1.391(3) . ? C23 C26 1.513(3) . ? C22 C21 1.384(3) . ? C14 C15 1.389(3) . ? C14 C19 1.397(3) . ? C14 C20 1.506(3) . ? C24 C25 1.385(3) . ? C19 F3B 1.155(10) . ? C19 C18 1.376(3) . ? C10 C11 1.383(3) . ? C10 C9 1.389(3) . ? C10 C13 1.515(3) . ? C16 F4B 1.267(12) . ? C16 C15 1.382(3) . ? C16 C17 1.384(3) . ? C20 O5 1.220(2) . ? C20 O4 1.305(2) . ? C26 O6 1.235(2) . ? C26 N4 1.324(3) . ? C7 O2 1.213(2) . ? C7 O1 1.311(3) . ? C7 C1 1.498(3) . ? C21 N3 1.334(3) . ? C15 F3A 1.340(2) . ? C17 C18 1.376(3) . ? C11 C12 1.385(3) . ? C9 C8 1.380(3) . ? C1 C2 1.391(3) . ? C1 C6 1.391(3) . ? C6 F1 1.351(2) . ? C6 C5 1.381(3) . ? C2 C3 1.373(3) . ? C13 O3 1.229(3) . ? C13 N2 1.331(3) . ? C8 N1 1.332(3) . ? C18 F4A 1.357(3) . ? C25 N3 1.337(3) . ? C4 C5 1.371(3) . ? C4 C3 1.380(4) . ? C12 N1 1.337(3) . ? C3 F2 1.355(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 C22 C23 C24 118.66(19) . . ? C22 C23 C26 117.47(18) . . ? C24 C23 C26 123.86(18) . . ? C21 C22 C23 119.2(2) . . ? C15 C14 C19 117.09(19) . . ? C15 C14 C20 122.49(18) . . ? C19 C14 C20 120.42(18) . . ? C25 C24 C23 118.41(19) . . ? F3B C19 C18 113.1(5) . . ? F3B C19 C14 127.5(5) . . ? C18 C19 C14 119.4(2) . . ? C11 C10 C9 117.89(19) . . ? C11 C10 C13 125.28(18) . . ? C9 C10 C13 116.84(18) . . ? F4B C16 C15 112.6(5) . . ? F4B C16 C17 127.9(5) . . ? C15 C16 C17 119.5(2) . . ? O5 C20 O4 124.08(18) . . ? O5 C20 C14 122.75(18) . . ? O4 C20 C14 113.16(17) . . ? O6 C26 N4 123.68(19) . . ? O6 C26 C23 118.62(18) . . ? N4 C26 C23 117.71(18) . . ? O2 C7 O1 123.2(2) . . ? O2 C7 C1 123.65(19) . . ? O1 C7 C1 113.17(18) . . ? N3 C21 C22 122.1(2) . . ? F3A C15 C16 116.40(18) . . ? F3A C15 C14 120.62(18) . . ? C16 C15 C14 122.95(19) . . ? C18 C17 C16 117.7(2) . . ? C10 C11 C12 119.12(19) . . ? C8 C9 C10 119.3(2) . . ? C2 C1 C6 117.4(2) . . ? C2 C1 C7 119.93(19) . . ? C6 C1 C7 122.62(19) . . ? F1 C6 C5 116.70(19) . . ? F1 C6 C1 120.66(18) . . ? C5 C6 C1 122.6(2) . . ? C3 C2 C1 119.4(2) . . ? O3 C13 N2 123.2(2) . . ? O3 C13 C10 119.05(18) . . ? N2 C13 C10 117.77(18) . . ? N1 C8 C9 123.0(2) . . ? F4A C18 C19 117.2(2) . . ? F4A C18 C17 119.4(2) . . ? C19 C18 C17 123.4(2) . . ? N3 C25 C24 122.7(2) . . ? C5 C4 C3 118.6(2) . . ? N1 C12 C11 122.9(2) . . ? C4 C5 C6 119.3(2) . . ? F2 C3 C2 118.7(2) . . ? F2 C3 C4 118.6(2) . . ? C2 C3 C4 122.7(2) . . ? C21 N3 C25 118.92(18) . . ? C8 N1 C12 117.80(19) . . ? _refine_diff_density_max 0.630 _refine_diff_density_min -0.254 _refine_diff_density_rms 0.056 _shelxl_version_number 2013-2 _shelx_res_file ; TITL datam in P-1 #2 CELL 0.71073 8.3252 12.1896 13.4770 107.408 102.834 94.816 ZERR 4.00 0.0006 0.0009 0.0010 0.008 0.007 0.007 LATT 1 SFAC C H N O F UNIT 52 32 8 12 8 MERG 2 FMAP 2 PLAN 20 SIZE 0.100 0.100 0.150 ACTA BOND L.S. 10 TEMP -123.00 WGHT 0.079500 0.462900 FVAR 0.44530 0.85360 0.85694 C23 1 0.158712 -0.036952 0.775078 11.00000 0.01781 0.02368 = 0.02107 0.00703 0.00611 0.00596 C22 1 0.130774 0.060031 0.744066 11.00000 0.02226 0.02257 = 0.02671 0.00801 0.00318 0.00188 C14 1 0.506993 0.982523 0.670550 11.00000 0.01931 0.01953 = 0.02019 0.00576 0.00548 0.00470 C24 1 0.057522 -0.143215 0.714121 11.00000 0.02162 0.02229 = 0.02548 0.00779 0.00573 0.00473 C19 1 0.617617 1.087381 0.721848 11.00000 0.02345 0.02250 = 0.02826 0.00808 0.00462 0.00253 C10 1 0.646291 0.458015 0.603728 11.00000 0.02313 0.02153 = 0.02214 0.00705 0.00559 0.00345 C16 1 0.662275 0.903517 0.801552 11.00000 0.03103 0.02920 = 0.02859 0.01438 0.00894 0.01195 C20 1 0.365302 0.970071 0.574386 11.00000 0.02087 0.01828 = 0.02018 0.00486 0.00668 0.00493 C26 1 0.298283 -0.020046 0.874460 11.00000 0.01787 0.02103 = 0.02130 0.00407 0.00485 0.00376 C7 1 0.095659 0.561507 0.817077 11.00000 0.02480 0.02193 = 0.02535 0.00687 0.00698 0.00426 C21 1 0.001502 0.048725 0.655209 11.00000 0.02482 0.02437 = 0.02817 0.01036 0.00400 0.00473 C15 1 0.534146 0.892445 0.712331 11.00000 0.02271 0.02073 = 0.02655 0.00820 0.00784 0.00506 C17 1 0.771291 1.007731 0.851673 11.00000 0.02578 0.03537 = 0.02524 0.00892 0.00427 0.00979 C11 1 0.560262 0.352197 0.595445 11.00000 0.02919 0.01800 = 0.03080 0.00397 0.00968 0.00341 C9 1 0.592083 0.558765 0.656399 11.00000 0.03125 0.01933 = 0.03334 0.00697 0.01342 0.00432 C1 1 -0.047446 0.570758 0.868075 11.00000 0.02226 0.02540 = 0.02288 0.00939 0.00498 0.00365 C6 1 -0.093964 0.676966 0.915786 11.00000 0.02596 0.02274 = 0.02627 0.00692 0.00706 0.00116 C2 1 -0.139057 0.470592 0.869414 11.00000 0.03176 0.02735 = 0.03905 0.01278 0.01687 0.00598 C13 1 0.796707 0.473575 0.560485 11.00000 0.02371 0.02217 = 0.02689 0.00598 0.00681 0.00120 C8 1 0.456322 0.549784 0.698089 11.00000 0.03410 0.01994 = 0.03654 0.00887 0.01674 0.00762 C18 1 0.745547 1.096921 0.810014 11.00000 0.02221 0.02794 = 0.03166 0.00452 0.00216 0.00092 C25 1 -0.069196 -0.146848 0.626485 11.00000 0.02173 0.02374 = 0.02324 0.00647 0.00286 0.00165 C4 1 -0.312917 0.586248 0.965349 11.00000 0.03696 0.04373 = 0.04848 0.01511 0.02738 0.01023 C12 1 0.425125 0.350910 0.639473 11.00000 0.03086 0.01981 = 0.03519 0.00493 0.01370 0.00122 C5 1 -0.223913 0.685688 0.964530 11.00000 0.03193 0.03274 = 0.03152 0.00701 0.01195 0.00809 C3 1 -0.269614 0.480271 0.916671 11.00000 0.03973 0.03317 = 0.05724 0.01880 0.02750 0.00266 N3 3 -0.097257 -0.052823 0.597870 11.00000 0.02225 0.02586 = 0.02534 0.00941 0.00413 0.00519 N4 3 0.324980 -0.112200 0.904644 11.00000 0.02108 0.02483 = 0.02532 0.00843 -0.00177 0.00178 N1 3 0.373544 0.448003 0.690596 11.00000 0.02967 0.02084 = 0.03533 0.00934 0.01437 0.00512 N2 3 0.848320 0.378087 0.507644 11.00000 0.02731 0.02093 = 0.03879 0.00362 0.01608 0.00225 O5 4 0.273318 0.877847 0.522036 11.00000 0.02390 0.01981 = 0.02738 0.00506 0.00063 0.00117 O6 4 0.380830 0.078143 0.922677 11.00000 0.02896 0.02153 = 0.02979 0.00466 -0.00372 0.00273 O2 4 0.181710 0.644869 0.813491 11.00000 0.03400 0.02375 = 0.04940 0.01144 0.02260 0.00335 O4 4 0.350734 1.067564 0.554250 11.00000 0.02856 0.01802 = 0.02817 0.00958 -0.00006 0.00187 O1 4 0.118663 0.453816 0.776330 11.00000 0.03995 0.02292 = 0.05270 0.00988 0.03021 0.00690 O3 4 0.864735 0.572631 0.575222 11.00000 0.03968 0.02085 = 0.05655 0.00603 0.02760 0.00010 F1 5 -0.012344 0.777612 0.915915 11.00000 0.03898 0.02356 = 0.04617 0.00688 0.01961 0.00329 F3A 5 0.431584 0.789898 0.668749 21.00000 0.03394 0.01602 = 0.03604 0.01223 -0.00215 -0.00071 F3B 5 0.613542 1.172663 0.701231 -21.00000 0.05779 0.04944 = 0.04320 0.02870 -0.00493 -0.00017 F4A 5 0.854168 1.198674 0.854223 31.00000 0.03235 0.02794 = 0.03803 0.00738 -0.01075 -0.00855 F4B 5 0.660748 0.812323 0.828276 -31.00000 0.04823 0.06622 = 0.03756 0.01299 -0.00285 0.02546 F2 5 -0.358842 0.381813 0.916261 11.00000 0.06908 0.04160 = 0.12635 0.03274 0.07093 0.00680 H24 2 0.071391 -0.213206 0.728724 11.00000 0.02640 H25 2 -0.138933 -0.215948 0.583555 11.00000 0.03040 H22 2 0.199150 0.132495 0.785236 11.00000 0.03545 H2 2 -0.116833 0.394021 0.833247 11.00000 0.04558 H12 2 0.360635 0.272616 0.633590 11.00000 0.04300 H21 2 -0.023961 0.117997 0.629888 11.00000 0.03870 H5 2 -0.248093 0.760902 1.000085 11.00000 0.03799 H9 2 0.644010 0.637303 0.664603 11.00000 0.03836 H11 2 0.593289 0.279512 0.562044 11.00000 0.04165 H4 2 -0.407969 0.591592 0.997154 11.00000 0.05120 H8 2 0.418575 0.621394 0.735244 11.00000 0.04073 H1 2 0.211756 0.455297 0.749584 11.00000 0.07360 H4A 2 0.403079 -0.101006 0.958015 11.00000 0.03269 H2A 2 0.944657 0.391913 0.482797 11.00000 0.04375 H4B 2 0.262157 -0.187338 0.868213 11.00000 0.04696 H2B 2 0.799645 0.305192 0.501187 11.00000 0.04716 HKLF 4 REM datam in P-1 #2 REM R1 = 0.0532 for 4106 Fo > 4sig(Fo) and 0.0782 for all 5746 data REM 445 parameters refined using 0 restraints END WGHT 0.0795 0.4629 REM Highest difference peak 0.630, deepest hole -0.254, 1-sigma level 0.056 Q1 1 0.8607 1.0242 0.9143 11.00000 0.05 0.63 Q2 1 0.2416 1.0610 0.4884 11.00000 0.05 0.41 Q3 1 0.7001 0.4717 0.5790 11.00000 0.05 0.25 Q4 1 0.0012 0.5735 0.8411 11.00000 0.05 0.23 Q5 1 0.6231 0.8962 0.7541 11.00000 0.05 0.23 Q6 1 0.6448 0.5015 0.6422 11.00000 0.05 0.23 Q7 1 0.4945 0.9398 0.7014 11.00000 0.05 0.22 Q8 1 0.2858 0.4404 0.6953 11.00000 0.05 0.21 Q9 1 -0.0483 0.6252 0.9091 11.00000 0.05 0.21 Q10 1 0.6564 1.1001 0.7823 11.00000 0.05 0.21 Q11 1 0.5871 0.9157 0.7723 11.00000 0.05 0.21 Q12 1 -0.0979 0.6186 0.8606 11.00000 0.05 0.20 Q13 1 0.0951 0.0446 0.6790 11.00000 0.05 0.20 Q14 1 0.7006 1.0798 0.7445 11.00000 0.05 0.20 Q15 1 0.0471 0.0632 0.7124 11.00000 0.05 0.20 Q16 1 0.2255 -0.0360 0.8208 11.00000 0.05 0.20 Q17 1 0.4631 0.9761 0.6239 11.00000 0.05 0.20 Q18 1 -0.1603 0.6790 0.9467 11.00000 0.05 0.20 Q19 1 -0.1907 0.6209 0.9767 11.00000 0.05 0.19 Q20 1 0.4483 0.8416 0.7200 11.00000 0.05 0.19 ; _shelx_res_checksum 91218 _shelx_hkl_file ; 0 0 2 52.64 0.82 0 0 -2 51.65 0.50 0 0 -2 50.71 0.78 0 0 3 44.14 1.01 0 0 -3 41.38 0.92 0 0 -3 42.72 0.56 0 0 4 595.66 6.59 0 0 -4 592.24 6.22 0 0 -4 583.20 4.03 0 0 5 199.86 3.34 0 0 -5 191.50 1.98 0 0 -5 192.57 3.13 0 0 6 37.80 1.42 0 0 -6 37.90 1.36 0 0 -6 37.49 0.76 0 0 7 4.10 0.86 0 0 -7 4.57 0.84 0 0 -7 5.04 0.38 0 0 8 96.13 2.88 0 0 -8 95.65 2.75 0 0 9 1.46 0.94 0 0 -9 1.72 0.90 0 0 -9 1.14 0.36 0 0 10 23.61 1.87 0 0 -10 18.93 1.77 0 0 11 0.13 1.16 0 0 -11 2.35 1.23 0 0 12 8.11 1.63 0 0 -12 5.76 1.49 0 0 13 3.91 1.70 0 0 -13 3.25 1.56 0 0 14 8.13 2.18 0 0 -14 14.91 2.11 0 0 15 5.58 1.94 0 0 -15 1.84 1.75 0 0 16 0.27 2.16 0 0 -16 1.22 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11 4.13 1.49 -2 8 -11 5.92 1.42 2 -8 12 44.99 2.98 -2 8 -12 42.74 2.82 2 -8 13 12.29 2.07 -2 8 -13 12.41 1.91 2 -8 14 7.50 1.89 -2 8 -14 5.13 1.74 2 -8 15 -2.43 1.53 -2 8 -15 -0.04 1.39 2 -7 -12 -0.11 1.41 -2 7 12 0.55 1.51 2 -7 -11 5.77 2.37 -2 7 11 5.11 2.04 2 -7 -10 23.87 2.55 -2 7 10 22.88 3.16 2 -7 -9 5.85 1.69 -2 7 9 7.88 1.77 2 -7 -8 11.21 1.82 -2 7 8 12.89 1.91 2 -7 -7 10.10 1.63 -2 7 7 15.64 1.74 2 -7 -6 0.96 0.95 -2 7 6 0.89 0.96 2 -7 -5 49.32 2.32 -2 7 5 54.88 2.82 2 -7 -4 13.72 1.38 -2 7 4 13.88 0.86 -2 7 4 12.88 1.37 2 -7 -3 69.44 2.30 -2 7 3 63.91 2.25 -2 7 3 57.71 1.59 2 -7 -2 1.28 0.65 2 -7 -2 1.23 0.74 2 -7 -2 2.26 0.71 2 -7 -1 45.22 1.55 2 -7 -1 44.80 1.74 2 -7 -1 46.25 1.60 2 -7 0 0.28 0.61 2 -7 0 1.64 0.60 2 -7 0 0.52 0.60 2 -7 1 31.30 1.14 2 -7 1 27.66 1.37 2 -7 1 28.76 1.31 2 -7 2 77.72 2.28 2 -7 2 76.85 2.31 -2 7 -2 69.91 1.56 2 -7 3 88.37 2.56 2 -7 3 94.63 2.38 -2 7 -3 87.66 1.76 2 -7 4 63.83 2.19 2 -7 4 55.06 1.89 -2 7 -4 55.10 1.26 2 -7 5 65.75 2.12 -2 7 -5 62.82 2.00 -2 7 -5 67.11 1.43 2 -7 6 23.32 1.37 -2 7 -6 19.88 1.42 -2 7 -6 16.51 0.84 2 -7 7 41.59 1.97 -2 7 -7 43.78 2.13 -2 7 -7 39.38 1.28 2 -7 8 87.19 2.94 -2 7 -8 75.31 1.96 -2 7 -8 89.33 3.03 2 -7 9 15.26 1.64 -2 7 -9 14.31 1.54 -2 7 -9 13.20 1.06 2 -7 10 25.82 2.04 -2 7 -10 22.50 1.37 -2 7 -10 21.97 1.92 2 -7 11 17.37 1.80 -2 7 -11 14.64 1.78 -2 7 -11 13.61 1.33 2 -7 12 12.77 1.91 -2 7 -12 14.93 1.80 -2 7 -12 13.08 1.14 2 -7 13 3.43 1.43 -2 7 -13 0.63 1.25 2 -7 14 4.24 1.81 -2 7 -14 4.25 1.49 2 -7 15 8.95 1.93 -2 7 -15 2.75 2.03 2 -6 -13 62.73 4.62 -2 6 13 67.25 4.64 2 -6 -12 41.89 3.46 -2 6 12 38.79 3.44 2 -6 -11 7.72 1.93 -2 6 11 7.81 1.98 2 -6 -10 -0.92 1.26 -2 6 10 -0.51 1.27 2 -6 -9 17.75 2.03 -2 6 9 25.01 2.21 2 -6 -8 -0.44 0.93 -2 6 8 0.73 0.97 2 -6 -7 0.74 1.02 -2 6 7 1.77 1.01 2 -6 -6 8.80 1.32 -2 6 6 9.92 1.37 2 -6 -5 46.26 2.05 -2 6 5 51.55 2.19 2 -6 -4 3.23 0.52 2 -6 -4 4.30 0.93 -2 6 4 4.23 0.89 2 -6 -3 20.64 1.24 2 -6 -3 18.41 0.95 -2 6 3 18.15 1.19 2 -6 -2 8.44 0.63 2 -6 -2 8.18 0.87 2 -6 -2 6.99 1.04 2 -6 -1 0.03 0.46 2 -6 -1 0.32 0.51 2 -6 -1 3.21 0.53 2 -6 0 56.73 1.55 2 -6 0 59.13 1.64 2 -6 0 52.70 1.59 2 -6 1 395.68 5.65 2 -6 1 406.12 6.10 2 -6 1 411.53 5.14 2 -6 2 16.73 1.13 2 -6 2 18.48 0.93 -2 6 -2 19.13 0.67 2 -6 3 1065.64 12.24 2 -6 3 1044.71 13.35 -2 6 -3 1024.75 9.70 2 -6 4 0.58 0.53 2 -6 4 1.03 0.65 -2 6 -4 0.52 0.37 2 -6 5 94.68 2.72 2 -6 5 97.78 2.52 -2 6 -5 97.41 1.85 2 -6 6 33.46 1.53 2 -6 6 31.06 1.68 -2 6 -6 31.73 1.14 2 -6 7 22.85 1.69 -2 6 -7 23.95 1.48 -2 6 -7 22.50 1.09 2 -6 8 142.22 3.79 -2 6 -8 137.83 3.01 -2 6 -8 151.41 3.90 2 -6 9 7.14 1.38 -2 6 -9 6.98 0.99 -2 6 -9 11.44 1.28 2 -6 10 13.60 1.56 -2 6 -10 13.23 1.45 -2 6 -10 14.40 1.05 2 -6 11 1.16 1.08 -2 6 -11 0.41 0.95 -2 6 -11 0.38 0.84 2 -6 12 13.80 1.81 -2 6 -12 10.62 1.25 -2 6 -12 10.36 1.84 2 -6 13 0.65 1.28 -2 6 -13 1.12 1.07 -2 6 -13 1.17 0.84 2 -6 14 3.11 1.59 -2 6 -14 3.05 1.57 -2 6 -14 1.86 1.39 2 -6 15 7.80 1.99 2 -6 16 12.31 2.33 2 -5 -14 18.52 2.93 -2 5 14 20.12 3.24 2 -5 -13 49.34 3.94 -2 5 13 55.20 4.10 2 -5 -12 8.82 2.04 -2 5 12 7.81 2.16 2 -5 -11 -1.31 1.28 -2 5 11 0.49 1.28 2 -5 -10 28.74 2.46 -2 5 10 29.06 2.44 2 -5 -9 15.00 1.89 -2 5 9 17.68 1.94 2 -5 -8 34.15 2.32 -2 5 8 38.11 2.36 2 -5 -7 29.16 1.83 -2 5 7 28.30 1.89 2 -5 -6 24.50 1.69 -2 5 6 25.39 1.63 2 -5 -5 0.77 0.35 2 -5 -5 1.70 0.77 -2 5 5 1.86 0.74 2 -5 -4 1.91 0.43 2 -5 -4 3.46 0.73 -2 5 4 2.13 0.72 2 -5 -3 406.84 5.02 2 -5 -3 403.00 6.32 -2 5 3 407.44 6.31 2 -5 -2 126.79 2.26 2 -5 -2 131.48 2.62 2 -5 -2 129.59 2.66 2 -5 -1 239.13 3.61 2 -5 -1 246.94 3.76 2 -5 -1 247.04 3.83 2 -5 0 214.74 3.37 2 -5 0 213.39 3.25 2 -5 0 206.89 3.42 2 -5 1 91.72 2.18 2 -5 1 94.16 1.87 2 -5 2 50.33 1.52 2 -5 2 46.62 1.24 -2 5 -2 47.42 1.11 2 -5 3 380.84 5.06 2 -5 3 390.33 5.92 -2 5 -3 379.24 4.41 2 -5 4 66.35 1.96 2 -5 4 60.44 1.65 -2 5 -4 64.99 1.37 2 -5 5 161.58 3.11 2 -5 5 162.70 3.74 -2 5 -5 162.69 2.55 2 -5 6 1.50 0.80 2 -5 6 1.51 0.84 -2 5 -6 2.31 0.51 2 -5 7 1.43 0.69 2 -5 7 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27.97 1.05 2 -4 -2 50.53 1.27 2 -4 -2 48.39 1.28 2 -4 -2 48.40 1.42 2 -4 -1 1211.60 11.44 2 -4 -1 1209.06 11.18 2 -4 -1 1212.45 11.89 2 -4 0 16.59 0.69 2 -4 0 14.75 0.78 2 -4 0 15.93 0.64 2 -4 1 377.95 4.92 2 -4 1 378.36 4.20 -2 4 -1 375.74 4.24 2 -4 2 11.01 0.78 2 -4 2 10.88 0.64 -2 4 -2 9.68 0.51 2 -4 3 70.05 1.80 2 -4 3 64.90 1.55 -2 4 -3 67.40 1.37 2 -4 4 13.37 0.92 2 -4 4 12.05 0.77 -2 4 -4 14.04 0.77 2 -4 5 0.14 0.45 2 -4 5 0.03 0.38 -2 4 -5 -0.11 0.40 2 -4 6 306.26 5.29 2 -4 6 311.21 5.21 -2 4 -6 313.64 4.75 2 -4 7 44.41 1.75 2 -4 7 42.62 1.86 -2 4 -7 46.58 1.74 2 -4 8 39.11 1.95 -2 4 -8 38.88 1.66 -2 4 -8 39.85 1.63 2 -4 9 1.43 0.90 -2 4 -9 0.18 0.66 -2 4 -9 0.85 0.72 2 -4 10 7.38 1.33 -2 4 -10 6.84 1.11 -2 4 -10 6.75 1.18 2 -4 11 0.21 0.87 -2 4 -11 0.09 0.62 -2 4 -11 -0.13 0.72 2 -4 12 19.43 2.06 -2 4 -12 20.40 1.56 -2 4 -12 22.43 1.81 2 -4 13 0.86 1.49 -2 4 -13 3.63 1.19 -2 4 -13 1.90 1.17 2 -4 14 3.38 1.62 -2 4 -14 3.00 1.62 2 -4 15 -0.29 1.46 -2 4 -15 1.77 1.56 2 -3 -15 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4.01 -2 -4 -9 90.97 4.11 2 4 10 -0.34 1.30 -2 -4 -10 -0.40 1.35 2 4 11 1.27 1.33 -2 -4 -11 -2.04 1.44 2 4 12 0.13 1.63 -2 -4 -12 2.06 1.61 2 4 13 8.11 2.51 -2 -5 17 2.20 1.90 -2 -5 16 8.83 2.23 2 5 -15 0.49 0.80 2 5 -15 -1.17 0.79 -2 -5 15 1.80 1.16 2 5 -14 70.24 3.35 2 5 -14 67.29 2.86 -2 -5 14 78.65 3.86 2 5 -13 14.81 1.38 2 5 -13 13.77 1.56 -2 -5 13 14.53 2.03 2 5 -12 0.06 0.67 2 5 -12 0.82 0.88 -2 -5 12 1.91 1.04 2 5 -11 37.34 2.02 2 5 -11 37.26 1.48 -2 -5 11 39.80 2.35 2 5 -10 4.52 1.27 2 5 -10 3.12 0.66 -2 -5 10 5.05 1.43 2 5 -9 81.18 1.79 2 5 -9 88.77 2.96 -2 -5 9 86.28 2.97 2 5 -8 25.01 1.47 -2 -5 8 20.18 1.49 2 5 -7 137.51 3.37 -2 -5 7 128.15 1.77 -2 -5 7 136.27 3.46 2 5 -6 24.19 1.44 -2 -5 6 24.18 0.61 -2 -5 6 28.62 1.39 2 5 -5 498.87 7.52 -2 -5 5 473.66 4.11 -2 -5 5 509.14 7.35 2 5 -4 311.57 5.26 -2 -5 4 319.58 5.01 -2 -5 4 314.10 3.11 2 5 -3 3.32 0.75 -2 -5 3 2.57 0.59 -2 -5 3 3.10 0.42 2 5 -2 14.85 1.04 -2 -5 2 15.50 0.66 -2 -5 2 16.06 0.95 2 5 -1 533.88 7.14 -2 -5 1 535.24 6.39 -2 -5 1 534.20 7.30 2 5 0 76.23 2.03 -2 -5 0 74.12 1.82 -2 -5 0 73.50 1.95 2 5 1 39.41 1.25 -2 -5 -1 41.39 1.59 -2 -5 -1 37.61 1.49 2 5 2 200.35 3.27 -2 -5 -2 207.20 4.20 2 5 3 2.29 0.84 2 5 3 2.74 0.55 -2 -5 -3 4.61 0.90 2 5 4 16.65 1.42 2 5 4 16.66 0.74 -2 -5 -4 13.84 1.57 2 5 5 1.28 0.98 -2 -5 -5 2.44 1.08 2 5 6 50.42 2.93 -2 -5 -6 44.75 2.75 2 5 7 120.29 4.46 -2 -5 -7 131.94 4.56 2 5 8 136.07 5.23 -2 -5 -8 132.46 5.07 2 5 9 33.72 2.83 -2 -5 -9 39.61 2.95 2 5 10 6.85 1.91 -2 -5 -10 7.48 1.96 2 5 11 10.48 2.46 -2 -5 -11 11.25 2.52 2 5 12 3.99 2.33 -2 -5 -12 7.90 2.32 -2 -6 17 3.11 1.99 2 6 -16 0.28 1.08 -2 -6 16 -0.32 1.30 2 6 -15 5.62 1.60 -2 -6 15 10.42 2.00 2 6 -14 6.28 1.45 -2 -6 14 8.20 1.92 2 6 -13 59.03 2.85 -2 -6 13 64.68 3.34 2 6 -12 5.56 1.28 -2 -6 12 3.99 1.44 2 6 -11 1.23 1.00 -2 -6 11 1.19 1.07 2 6 -10 -0.21 0.34 2 6 -10 0.93 0.77 -2 -6 10 0.49 0.81 2 6 -9 73.41 2.84 -2 -6 9 84.75 2.98 2 6 -8 -0.35 0.72 -2 -6 8 0.52 0.75 2 6 -7 100.31 3.05 -2 -6 7 100.92 3.02 2 6 -6 26.06 1.59 -2 -6 6 26.54 1.48 2 6 -5 141.49 3.44 -2 -6 5 143.71 3.32 2 6 -4 318.68 5.63 -2 -6 4 308.26 5.39 -2 -6 4 299.89 3.19 2 6 -3 72.61 2.19 -2 -6 3 74.65 1.40 -2 -6 3 75.46 2.15 2 6 -2 153.91 3.31 -2 -6 2 146.43 2.38 -2 -6 2 152.68 3.46 2 6 -1 96.87 2.44 -2 -6 1 94.90 2.01 -2 -6 1 95.17 2.48 2 6 0 2.38 0.65 -2 -6 0 0.63 0.58 -2 -6 0 1.51 0.73 2 6 1 4.98 0.69 -2 -6 -1 5.60 0.97 -2 -6 -1 3.89 0.95 2 6 2 5.71 0.85 -2 -6 -2 7.68 1.10 -2 -6 -2 8.75 1.16 2 6 3 19.81 1.39 2 6 3 16.89 0.93 -2 -6 -3 16.39 1.45 2 6 4 -0.44 0.72 -2 -6 -4 0.66 0.94 2 6 5 27.55 1.98 -2 -6 -5 25.88 2.00 2 6 6 -0.00 1.35 -2 -6 -6 1.77 1.15 2 6 7 71.77 3.37 -2 -6 -7 63.79 3.54 2 6 8 17.91 2.39 -2 -6 -8 24.05 2.36 2 6 9 34.13 3.62 -2 -6 -9 36.04 3.17 2 6 10 7.51 1.99 -2 -6 -10 10.70 2.15 2 6 11 5.31 2.23 -2 -6 -11 4.75 2.23 2 7 -17 9.85 2.24 -2 -7 17 10.47 2.97 2 7 -16 13.12 2.13 -2 -7 16 17.50 2.68 2 7 -15 8.42 1.66 -2 -7 15 8.86 2.20 2 7 -14 3.41 1.27 -2 -7 14 1.75 1.61 2 7 -13 11.80 1.70 -2 -7 13 14.15 1.93 2 7 -12 23.39 2.44 -2 -7 12 26.76 2.27 2 7 -11 72.16 3.10 -2 -7 11 64.75 3.60 2 7 -10 20.26 1.89 -2 -7 10 21.29 1.87 2 7 -9 -0.14 0.79 -2 -7 9 0.47 0.86 2 7 -8 2.92 1.05 -2 -7 8 3.17 1.13 2 7 -7 -0.44 0.80 -2 -7 7 -0.08 0.72 2 7 -6 2.93 0.96 -2 -7 6 0.55 0.88 2 7 -5 9.71 1.32 -2 -7 5 11.75 1.13 2 7 -4 32.13 1.64 -2 -7 4 27.22 0.78 -2 -7 4 32.68 1.54 2 7 -3 36.27 1.78 -2 -7 3 35.15 1.05 -2 -7 3 38.49 1.70 2 7 -2 106.63 2.86 -2 -7 2 100.62 1.99 -2 -7 2 106.28 2.91 2 7 -1 25.30 1.37 -2 -7 1 25.25 1.28 -2 -7 1 24.06 1.47 2 7 0 8.26 1.06 -2 -7 0 5.42 0.87 -2 -7 0 7.62 1.13 2 7 1 23.81 1.38 -2 -7 -1 26.12 1.44 -2 -7 -1 19.23 1.61 2 7 2 19.84 1.28 -2 -7 -2 24.92 1.77 -2 -7 -2 23.97 1.54 2 7 3 21.52 1.64 2 7 3 17.45 0.96 -2 -7 -3 24.10 1.94 2 7 4 4.20 1.24 -2 -7 -4 4.20 1.23 2 7 5 12.33 2.21 -2 -7 -5 15.75 1.76 2 7 6 72.68 3.54 -2 -7 -6 80.45 3.54 2 7 7 28.09 2.57 -2 -7 -7 26.53 2.53 2 7 8 12.24 2.18 -2 -7 -8 12.49 2.16 2 7 9 8.84 2.27 -2 -7 -9 11.91 2.69 2 7 10 2.60 1.95 -2 -7 -10 4.33 2.01 2 8 -17 1.42 1.80 -2 -8 17 1.08 1.81 2 8 -16 67.36 3.94 -2 -8 16 65.06 4.39 2 8 -15 9.78 1.97 -2 -8 15 14.33 2.38 2 8 -14 42.20 3.47 -2 -8 14 44.31 3.37 2 8 -13 23.01 2.23 -2 -8 13 26.16 2.49 2 8 -12 -0.40 1.07 -2 -8 12 1.47 1.19 2 8 -11 0.12 1.65 -2 -8 11 4.92 1.35 2 8 -10 7.42 1.60 -2 -8 10 7.19 1.47 2 8 -9 79.97 3.37 -2 -8 9 83.55 3.43 2 8 -8 5.05 1.39 -2 -8 8 5.11 1.30 2 8 -7 19.60 1.63 -2 -8 7 19.84 1.60 2 8 -6 14.74 1.71 -2 -8 6 19.87 1.57 2 8 -5 12.56 1.48 -2 -8 5 12.23 1.33 2 8 -4 18.75 1.49 -2 -8 4 14.28 0.63 -2 -8 4 15.57 1.38 2 8 -3 7.72 1.08 -2 -8 3 3.60 0.60 -2 -8 3 7.70 1.09 2 8 -2 47.08 2.27 -2 -8 2 46.76 2.08 -2 -8 2 44.79 1.49 2 8 -1 33.22 1.69 -2 -8 1 32.94 1.32 -2 -8 1 30.75 1.85 2 8 0 81.77 2.53 -2 -8 0 87.52 2.44 -2 -8 0 82.85 2.99 2 8 1 33.62 1.73 -2 -8 -1 31.47 1.73 -2 -8 -1 32.54 2.15 2 8 2 1.05 0.57 -2 -8 -2 -0.58 0.72 -2 -8 -2 -0.58 0.91 2 8 3 279.17 7.10 -2 -8 -3 285.34 7.05 2 8 4 102.22 4.01 -2 -8 -4 102.82 3.82 2 8 5 21.19 2.19 -2 -8 -5 18.88 2.15 2 8 6 71.58 3.91 -2 -8 -6 72.43 3.77 2 8 7 -0.42 1.30 -2 -8 -7 0.82 1.20 2 8 8 0.61 1.61 -2 -8 -8 2.96 1.65 2 8 9 40.18 3.77 -2 -8 -9 36.96 3.59 2 9 -16 1.03 1.28 -2 -9 16 -1.64 1.47 2 9 -15 -0.25 1.21 -2 -9 15 -0.51 1.38 2 9 -14 67.33 3.80 -2 -9 14 70.06 4.08 2 9 -13 1.13 1.23 -2 -9 13 -0.59 1.31 2 9 -12 1.48 1.09 -2 -9 12 -2.07 1.16 2 9 -11 5.30 1.56 -2 -9 11 1.76 1.61 2 9 -10 0.35 1.52 -2 -9 10 2.40 1.22 2 9 -9 -1.54 0.88 -2 -9 9 1.35 0.82 2 9 -8 4.94 1.46 -2 -9 8 5.97 1.34 2 9 -7 0.42 1.09 -2 -9 7 1.04 0.96 2 9 -6 36.08 2.27 -2 -9 6 32.28 2.12 2 9 -5 23.17 1.87 -2 -9 5 22.28 1.77 2 9 -4 347.65 7.36 -2 -9 4 343.02 7.47 2 9 -3 116.22 3.53 -2 -9 3 109.14 2.32 -2 -9 3 121.01 3.63 2 9 -2 11.79 1.30 -2 -9 2 8.62 0.93 -2 -9 2 10.01 1.42 2 9 -1 4.25 1.02 -2 -9 1 4.17 0.74 -2 -9 1 4.63 1.25 2 9 0 1.91 1.11 -2 -9 0 2.51 0.80 -2 -9 0 2.71 1.18 2 9 1 0.50 0.72 -2 -9 -1 0.96 0.84 -2 -9 -1 -1.35 0.81 2 9 2 36.28 1.96 -2 -9 -2 44.74 2.57 -2 -9 -2 41.49 2.53 2 9 3 13.85 1.92 -2 -9 -3 10.72 1.98 2 9 4 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54.87 1.63 -4 7 -1 62.66 2.00 4 -7 2 9.83 1.30 4 -7 2 11.12 0.98 -4 7 -2 9.16 0.97 4 -7 3 195.24 4.93 4 -7 3 193.79 3.84 -4 7 -3 203.91 4.06 4 -7 4 4.22 1.17 4 -7 4 4.90 0.72 -4 7 -4 4.43 0.73 4 -7 5 237.87 4.67 4 -7 5 255.88 6.00 -4 7 -5 240.86 4.70 4 -7 6 -0.06 0.98 4 -7 6 1.22 0.67 -4 7 -6 0.13 0.67 4 -7 7 88.15 3.31 4 -7 7 88.08 2.80 -4 7 -7 84.28 2.69 4 -7 8 -0.20 0.79 -4 7 -8 0.14 0.60 4 -7 9 6.11 1.56 4 -7 9 4.51 1.21 -4 7 -9 8.51 1.17 4 -7 10 0.90 1.21 -4 7 -10 1.38 0.89 -4 7 -10 0.14 0.77 4 -7 11 2.30 1.48 -4 7 -11 1.12 1.30 -4 7 -11 1.94 1.27 4 -7 12 2.02 1.34 -4 7 -12 1.39 1.62 -4 7 -12 1.94 1.38 4 -7 13 51.89 3.81 -4 7 -13 51.74 3.44 4 -7 14 -0.43 1.55 -4 7 -14 3.55 1.83 4 -6 -13 4.59 2.07 -4 6 13 2.47 1.87 4 -6 -12 3.85 1.85 -4 6 12 4.31 1.87 4 -6 -11 1.89 1.46 -4 6 11 1.37 1.47 4 -6 -10 3.13 1.46 -4 6 10 2.50 1.34 4 -6 -9 4.52 1.62 -4 6 9 2.03 1.22 4 -6 -8 27.86 2.20 -4 6 8 25.52 2.41 4 -6 -7 1.00 0.48 4 -6 -7 -1.75 0.81 -4 6 7 -1.02 0.73 4 -6 -6 2.82 0.68 4 -6 -6 5.08 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1.08 -4 -8 2 4.44 0.97 4 8 -1 83.42 3.18 -4 -8 1 87.20 2.95 -4 -8 1 84.35 3.23 4 8 0 201.31 5.44 -4 -8 0 216.63 5.65 -4 -8 0 206.13 5.64 4 8 1 9.49 1.44 -4 -8 -1 9.70 1.52 -4 -8 -1 8.46 1.52 4 8 2 25.29 2.04 4 8 2 18.35 1.77 -4 -8 -2 21.28 2.38 4 8 3 -1.28 0.95 -4 -8 -3 1.19 1.00 4 8 4 2.80 1.52 -4 -8 -4 4.94 1.56 4 8 5 2.35 1.73 -4 -8 -5 7.36 1.78 4 8 6 34.75 3.04 -4 -8 -6 29.93 3.20 4 8 7 0.68 1.26 -4 -8 -7 -0.66 1.41 4 9 -16 0.99 2.01 -4 -9 16 0.94 1.71 4 9 -15 1.74 1.59 -4 -9 15 0.53 1.64 4 9 -14 0.62 2.08 -4 -9 14 20.37 2.39 4 9 -13 1.17 1.43 -4 -9 13 0.38 1.38 4 9 -12 1.48 1.83 -4 -9 12 7.45 1.92 4 9 -11 11.82 2.35 -4 -9 11 15.10 2.35 4 9 -10 0.88 1.02 -4 -9 10 -0.64 0.89 4 9 -9 12.29 2.21 -4 -9 9 17.87 2.02 4 9 -8 1.15 1.24 -4 -9 8 -0.08 1.01 4 9 -7 31.63 2.57 -4 -9 7 30.38 2.17 4 9 -6 2.10 1.68 -4 -9 6 1.54 1.09 4 9 -5 189.09 5.63 -4 -9 5 180.37 3.90 -4 -9 5 203.36 5.25 4 9 -4 1.98 1.16 -4 -9 4 1.01 0.73 -4 -9 4 -0.21 0.95 4 9 -3 16.98 1.88 -4 -9 3 15.16 1.48 -4 -9 3 15.99 1.62 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122.73 4.71 -4 -10 1 112.52 3.86 -4 -10 1 123.83 4.48 4 10 0 55.39 3.26 -4 -10 0 59.32 3.22 -4 -10 0 55.15 3.26 4 10 1 2.34 1.26 4 10 1 0.52 1.05 -4 -10 -1 0.35 1.09 4 10 2 0.22 1.19 -4 -10 -2 0.52 1.16 4 10 3 -0.22 1.10 -4 -10 -3 0.39 1.32 4 10 4 0.72 1.36 -4 -10 -4 -0.30 1.26 4 10 5 2.05 2.18 -4 -10 -5 10.97 2.25 4 11 -14 34.30 3.57 -4 -11 14 36.01 3.44 4 11 -13 6.19 2.13 -4 -11 13 1.50 1.78 4 11 -12 1.86 1.88 -4 -11 12 4.14 1.71 4 11 -11 8.53 2.42 -4 -11 11 13.11 2.09 4 11 -10 -1.25 1.49 -4 -11 10 -0.05 1.34 4 11 -9 4.53 1.82 -4 -11 9 3.89 1.51 4 11 -8 1.95 1.57 -4 -11 8 1.39 1.28 4 11 -7 79.72 4.07 -4 -11 7 81.42 3.91 4 11 -6 31.75 3.09 -4 -11 6 27.81 2.72 4 11 -5 2.54 1.54 -4 -11 5 2.14 1.23 4 11 -4 6.90 1.65 -4 -11 4 4.79 1.52 4 11 -3 6.85 1.69 -4 -11 3 8.27 1.66 4 11 -2 6.79 1.40 -4 -11 2 3.58 1.27 -4 -11 2 1.05 1.75 4 11 -1 0.73 1.26 -4 -11 1 -1.15 1.05 -4 -11 1 1.97 1.17 4 11 0 6.31 1.51 -4 -11 0 13.09 1.84 -4 -11 0 7.08 1.81 4 11 1 1.17 1.79 -4 -11 -1 1.03 1.16 4 11 2 3.77 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0.75 -5 7 -6 1.49 1.18 5 -7 7 1.65 1.22 5 -7 7 1.36 0.78 -5 7 -7 2.19 1.13 5 -7 8 7.11 1.74 5 -7 8 9.94 1.22 -5 7 -8 8.90 1.38 5 -7 9 11.88 1.92 5 -7 9 11.31 1.40 -5 7 -9 12.71 1.54 5 -7 10 27.90 2.58 5 -7 10 27.65 2.44 -5 7 -10 30.43 2.58 5 -7 11 6.55 1.86 -5 7 -11 9.01 1.61 5 -7 12 3.73 1.38 -5 7 -12 -0.13 1.55 -5 7 -12 2.96 1.42 5 -7 13 0.11 1.94 -5 7 -13 4.51 2.14 5 -6 -13 -1.30 1.87 -5 6 13 -1.21 2.01 5 -6 -12 10.51 1.97 -5 6 12 2.85 1.84 5 -6 -11 4.64 1.79 -5 6 11 3.95 1.59 5 -6 -10 71.61 3.78 -5 6 10 66.10 3.76 5 -6 -9 3.63 1.52 -5 6 9 3.27 1.42 5 -6 -8 11.71 1.60 5 -6 -8 7.28 0.92 -5 6 8 8.26 1.52 5 -6 -7 8.80 1.52 5 -6 -7 5.96 1.08 -5 6 7 6.76 1.12 5 -6 -6 124.89 4.11 5 -6 -6 125.37 3.54 -5 6 6 132.20 3.64 5 -6 -5 21.89 1.88 5 -6 -5 20.41 1.36 -5 6 5 20.77 1.21 5 -6 -4 66.80 3.01 5 -6 -4 64.60 2.32 -5 6 4 67.57 2.00 5 -6 -3 57.32 2.45 5 -6 -3 59.71 2.45 -5 6 3 60.21 1.73 5 -6 -2 26.36 1.61 -5 6 2 23.11 1.07 -5 6 2 20.40 1.43 5 -6 -1 38.01 1.33 5 -6 -1 34.36 2.17 -5 6 1 35.78 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0.81 1.37 -9 -5 8 -0.35 1.04 9 5 -7 5.15 1.98 -9 -5 7 0.97 1.80 9 5 -6 10.96 2.89 -9 -5 6 9.91 1.92 9 5 -5 1.19 1.66 -9 -5 5 1.49 1.77 9 5 -4 0.31 1.55 -9 -5 4 1.67 1.31 9 5 -3 27.55 3.42 -9 -5 3 25.09 2.68 9 5 -2 24.23 2.40 -9 -5 2 0.46 2.17 9 5 -1 2.45 1.70 -9 -5 1 1.49 1.64 9 5 0 8.77 2.18 -9 -5 0 10.58 2.76 9 6 -10 0.34 1.54 9 6 -9 31.26 3.50 -9 -6 9 22.13 2.85 9 6 -8 -0.16 1.35 -9 -6 8 0.12 1.19 9 6 -7 4.29 2.05 -9 -6 7 4.76 1.62 9 6 -6 5.48 2.09 -9 -6 6 3.34 1.68 9 6 -5 0.86 2.24 -9 -6 5 2.81 1.78 9 6 -4 2.97 1.84 -9 -6 4 2.85 1.60 9 6 -3 -0.31 1.58 -9 -6 3 2.06 1.53 9 6 -2 2.65 2.04 -9 -6 2 1.29 1.55 9 6 -1 9.74 2.47 -9 -6 1 3.33 2.68 9 7 -9 9.39 2.75 9 7 -8 17.99 3.06 9 7 -7 -0.10 1.57 -9 -7 7 -0.27 1.36 9 7 -6 25.51 3.33 -9 -7 6 29.78 2.91 9 7 -5 14.78 2.78 -9 -7 5 12.43 2.60 9 7 -4 9.20 2.29 -9 -7 4 5.70 1.97 9 7 -3 0.28 1.49 -9 -7 3 0.41 1.34 10 -7 -3 4.69 2.05 10 -7 -2 5.70 2.10 -10 7 2 4.37 2.72 10 -7 -1 2.77 2.10 -10 7 1 5.30 2.11 10 -7 0 4.52 1.92 -10 7 0 -0.19 1.88 10 -6 -5 13.66 2.55 -10 6 5 9.18 2.76 10 -6 -4 12.93 2.54 -10 6 4 10.73 2.71 10 -6 -3 25.41 3.70 -10 6 3 22.56 2.96 10 -6 -2 -0.10 1.38 -10 6 2 -0.01 1.32 10 -6 -1 -0.06 1.74 -10 6 1 -1.48 1.69 10 -6 0 2.89 2.15 -10 6 0 4.20 2.07 10 -6 1 -0.11 1.70 -10 6 -1 1.87 1.68 10 -5 -7 7.09 2.31 10 -5 -6 22.83 3.46 -10 5 6 18.87 2.96 10 -5 -5 24.67 3.04 -10 5 5 24.30 3.17 10 -5 -4 1.58 1.66 -10 5 4 0.35 1.77 10 -5 -3 0.28 1.76 -10 5 3 3.11 2.18 10 -5 -2 -0.48 1.79 -10 5 2 -3.12 1.78 10 -5 -1 4.92 2.60 -10 5 1 3.21 1.90 10 -5 0 6.33 2.15 -10 5 0 3.18 2.14 10 -5 1 -1.04 1.30 -10 5 -1 1.04 1.36 10 -5 2 17.85 2.87 -10 5 -2 20.39 2.95 10 -4 -8 -0.05 1.34 10 -4 -7 2.76 1.66 -10 4 7 -0.31 1.76 10 -4 -6 19.14 3.45 -10 4 6 16.73 2.97 10 -4 -5 13.19 2.67 -10 4 5 14.88 2.67 10 -4 -4 14.14 2.65 -10 4 4 13.29 2.52 10 -4 -3 0.96 1.57 -10 4 3 1.32 1.68 10 -4 -2 0.47 1.35 -10 4 2 -0.45 1.25 10 -4 -1 7.99 2.23 -10 4 1 5.98 2.26 10 -4 0 18.67 2.90 -10 4 0 15.77 3.31 10 -4 1 13.62 2.86 -10 4 -1 19.67 2.76 10 -4 2 10.54 2.54 -10 4 -2 8.15 2.44 10 -3 -8 4.72 2.23 -10 3 8 2.62 2.21 10 -3 -7 0.29 1.72 -10 3 7 2.37 1.80 10 -3 -6 5.85 2.17 -10 3 6 9.50 2.38 10 -3 -5 13.68 2.75 -10 3 5 8.24 2.35 10 -3 -4 0.29 1.96 -10 3 4 -1.55 1.96 10 -3 -3 0.11 1.27 -10 3 3 -0.07 1.11 10 -3 -2 7.91 2.21 -10 3 2 4.13 2.68 10 -3 -1 3.00 1.92 -10 3 1 1.90 1.77 10 -3 0 24.19 3.14 -10 3 0 27.83 3.04 10 -3 1 4.79 2.08 -10 3 -1 4.42 2.17 10 -3 2 23.74 3.68 -10 3 -2 26.81 3.33 10 -2 -9 1.28 1.58 -10 2 9 -0.71 1.64 10 -2 -8 -0.14 1.78 -10 2 8 3.73 1.83 10 -2 -7 15.46 2.75 -10 2 7 14.91 2.83 10 -2 -6 10.74 2.53 -10 2 6 11.04 2.42 10 -2 -5 6.78 2.28 -10 2 5 5.81 2.09 10 -2 -4 8.70 2.38 -10 2 4 13.98 2.47 10 -2 -3 1.48 1.63 -10 2 3 -0.02 1.63 10 -2 -2 15.56 2.53 -10 2 2 11.97 2.60 10 -2 -1 0.84 1.37 -10 2 1 -1.26 1.42 10 -2 0 4.27 2.23 -10 2 0 9.79 2.30 10 -2 1 35.62 3.90 -10 2 -1 26.89 3.45 10 -2 2 -0.98 1.55 -10 2 -2 -0.15 1.63 10 -1 -9 -0.77 1.87 -10 1 9 -0.04 1.57 10 -1 -8 1.25 1.57 -10 1 8 -0.77 2.04 10 -1 -7 1.01 1.92 -10 1 7 3.89 1.92 10 -1 -6 2.08 2.12 -10 1 6 1.12 1.71 10 -1 -5 3.95 2.15 -10 1 5 2.57 1.94 10 -1 -4 15.30 2.60 -10 1 4 11.34 2.58 10 -1 -3 2.23 1.91 -10 1 3 0.89 2.28 10 -1 -2 5.09 2.10 -10 1 2 5.93 2.22 10 -1 -1 9.25 2.35 -10 1 1 10.53 2.43 10 -1 0 3.46 1.76 -10 1 0 0.39 2.07 10 -1 1 -0.49 1.47 -10 1 -1 1.03 1.58 10 -1 2 1.91 1.73 -10 1 -2 0.96 1.78 10 0 -10 -1.64 1.90 10 0 -9 4.86 2.14 -10 0 9 2.41 2.01 10 0 -8 8.21 2.76 -10 0 8 4.12 2.57 10 0 -7 1.93 1.83 -10 0 7 1.59 1.73 10 0 -6 -2.23 1.84 -10 0 6 -1.23 2.00 10 0 -5 0.80 1.61 -10 0 5 1.09 1.56 10 0 -4 28.65 3.43 -10 0 4 32.96 3.36 10 0 -3 31.58 3.35 -10 0 3 28.79 3.32 10 0 -2 9.54 2.42 -10 0 2 7.61 2.28 10 0 -1 4.29 2.01 -10 0 1 3.61 2.11 10 0 0 4.71 2.05 -10 0 0 5.78 2.66 10 0 1 4.13 2.06 -10 0 -1 9.12 2.23 10 1 -10 -0.87 1.75 10 1 -9 2.13 2.17 -10 -1 9 5.56 1.98 10 1 -8 -0.25 2.07 -10 -1 8 8.38 1.99 10 1 -7 -0.74 1.67 -10 -1 7 1.85 1.53 10 1 -6 6.51 2.26 -10 -1 6 5.36 2.06 10 1 -5 13.19 2.95 -10 -1 5 20.92 2.82 10 1 -4 91.70 5.22 -10 -1 4 98.85 5.79 10 1 -3 50.26 3.94 -10 -1 3 54.53 4.07 10 1 -2 31.51 3.56 -10 -1 2 37.10 4.03 10 1 -1 1.75 2.23 -10 -1 1 1.97 1.93 10 1 0 3.22 1.74 -10 -1 0 -0.88 1.87 10 1 1 1.47 1.46 -10 -1 -1 -0.94 1.73 10 2 -9 6.77 2.30 -10 -2 9 6.25 2.58 10 2 -8 0.30 2.45 -10 -2 8 2.83 1.64 10 2 -7 -2.39 1.87 -10 -2 7 0.95 1.38 10 2 -6 -1.19 1.82 -10 -2 6 -0.50 1.89 10 2 -5 0.47 1.63 -10 -2 5 -0.78 1.37 10 2 -4 52.67 4.20 -10 -2 4 53.40 3.94 10 2 -3 21.97 3.11 -10 -2 3 27.56 3.11 10 2 -2 0.19 1.59 -10 -2 2 -1.27 1.61 10 2 -1 0.30 1.53 -10 -2 1 0.34 1.91 10 2 0 5.09 2.34 -10 -2 0 9.59 2.38 10 3 -9 8.01 2.48 -10 -3 9 5.42 2.05 10 3 -8 3.42 2.45 -10 -3 8 8.85 2.10 10 3 -7 10.49 2.55 -10 -3 7 7.59 2.25 10 3 -6 32.61 3.54 -10 -3 6 36.77 3.92 10 3 -5 22.54 3.24 -10 -3 5 22.38 2.87 10 3 -4 71.71 4.84 -10 -3 4 77.14 4.69 10 3 -3 27.30 3.36 -10 -3 3 31.17 3.28 10 3 -2 0.96 1.29 -10 -3 2 -0.96 1.28 10 3 -1 9.63 3.04 -10 -3 1 10.66 2.67 10 4 -8 0.28 1.76 -10 -4 8 0.98 1.78 10 4 -7 20.32 3.25 -10 -4 7 21.13 3.33 10 4 -6 39.54 3.94 -10 -4 6 42.18 3.50 10 4 -5 4.74 2.11 -10 -4 5 1.97 1.92 10 4 -4 -0.95 1.55 -10 -4 4 0.33 1.53 10 4 -3 1.05 1.73 -10 -4 3 0.27 1.61 0 0 0 0.00 0.00 ; _shelx_hkl_checksum 83604 _database_code_depnum_ccdc_archive 'CCDC 965667' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_datam _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H10 F2 N2 O3' _chemical_formula_weight 280.23 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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.2755(7) _cell_length_b 7.6883(8) _cell_length_c 12.5950(13) _cell_angle_alpha 73.583(5) _cell_angle_beta 84.326(6) _cell_angle_gamma 66.372(5) _cell_volume 619.06(11) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.503 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 288 _exptl_absorpt_coefficient_mu 0.128 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9749 _exptl_absorpt_correction_T_max 0.9873 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6605 _diffrn_reflns_av_R_equivalents 0.0139 _diffrn_reflns_av_sigmaI/netI 0.0168 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2839 _reflns_number_gt 2517 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0587P)^2^+0.1581P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2839 _refine_ls_number_parameters 218 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0406 _refine_ls_R_factor_gt 0.0356 _refine_ls_wR_factor_ref 0.1061 _refine_ls_wR_factor_gt 0.0983 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _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 0.15235(16) 0.35120(17) 0.81525(9) 0.0202(2) Uani 1 1 d . . . C2 C 0.21598(17) 0.14602(17) 0.89197(9) 0.0216(2) Uani 1 1 d . . . C3 C 0.14466(18) 0.51074(18) 0.84985(10) 0.0231(2) Uani 1 1 d . . . C4 C 0.09945(18) 0.39473(18) 0.70455(10) 0.0229(3) Uani 1 1 d . . . C5 C 0.0435(2) 0.5811(2) 0.63274(11) 0.0299(3) Uani 1 1 d . . . C6 C 0.0889(2) 0.70018(19) 0.78153(12) 0.0301(3) Uani 1 1 d . . . C7 C 0.0385(2) 0.7331(2) 0.67232(12) 0.0328(3) Uani 1 1 d . . . O1 O 0.16063(16) 0.14521(13) 0.99296(7) 0.0328(2) Uani 1 1 d . . . H1 H 0.2176 0.0314 1.0347 0.049 Uiso 1 1 calc R . . O2 O 0.30872(15) -0.00029(13) 0.85978(7) 0.0323(2) Uani 1 1 d . . . F1 F 0.20220(12) 0.47960(11) 0.95401(6) 0.0323(2) Uani 1 1 d . . . F2 F 0.09669(12) 0.24913(11) 0.66591(6) 0.0323(2) Uani 1 1 d . . . C8 C 0.39493(18) 0.61591(17) 0.32311(10) 0.0226(2) Uani 1 1 d . . . C9 C 0.38555(18) 0.46574(17) 0.18216(10) 0.0224(2) Uani 1 1 d . . . C10 C 0.41659(17) 0.44869(16) 0.29271(9) 0.0194(2) Uani 1 1 d . . . C11 C 0.46419(18) 0.25789(17) 0.38232(9) 0.0219(2) Uani 1 1 d . . . C12 C 0.34042(19) 0.79390(17) 0.24322(10) 0.0240(3) Uani 1 1 d . . . C13 C 0.33023(19) 0.64994(18) 0.10764(10) 0.0242(3) Uani 1 1 d . . . N1 N 0.30677(16) 0.81100(14) 0.13696(8) 0.0233(2) Uani 1 1 d . . . N2 N 0.53813(18) 0.09187(15) 0.35165(9) 0.0279(3) Uani 1 1 d . . . O3 O 0.42821(15) 0.26422(13) 0.47944(7) 0.0308(2) Uani 1 1 d . . . H2A H 0.566(3) -0.022(3) 0.4038(15) 0.041(5) Uiso 1 1 d . . . H2B H 0.579(2) 0.084(2) 0.2855(15) 0.035(4) Uiso 1 1 d . . . H5 H 0.008(3) 0.601(3) 0.5620(15) 0.039(4) Uiso 1 1 d . . . H6 H 0.090(3) 0.800(3) 0.8108(14) 0.039(4) Uiso 1 1 d . . . H7 H -0.008(3) 0.871(3) 0.6218(16) 0.051(5) Uiso 1 1 d . . . H8 H 0.413(2) 0.612(2) 0.3958(13) 0.025(4) Uiso 1 1 d . . . H9 H 0.399(2) 0.362(2) 0.1562(12) 0.026(4) Uiso 1 1 d . . . H12 H 0.324(2) 0.912(2) 0.2608(12) 0.028(4) Uiso 1 1 d . . . H13 H 0.305(2) 0.669(2) 0.0312(14) 0.033(4) 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 0.0183(5) 0.0217(6) 0.0177(5) -0.0040(4) 0.0015(4) -0.0063(4) C2 0.0232(5) 0.0222(6) 0.0189(5) -0.0054(4) 0.0002(4) -0.0082(4) C3 0.0233(6) 0.0264(6) 0.0201(5) -0.0071(5) 0.0016(4) -0.0098(5) C4 0.0223(5) 0.0250(6) 0.0199(5) -0.0074(5) 0.0008(4) -0.0070(5) C5 0.0287(6) 0.0329(7) 0.0197(6) -0.0013(5) -0.0033(5) -0.0067(5) C6 0.0312(7) 0.0236(6) 0.0351(7) -0.0083(5) 0.0032(5) -0.0108(5) C7 0.0324(7) 0.0238(6) 0.0313(7) 0.0022(5) 0.0008(5) -0.0064(5) O1 0.0478(6) 0.0209(4) 0.0169(4) -0.0022(3) 0.0042(4) -0.0032(4) O2 0.0480(6) 0.0215(4) 0.0231(4) -0.0077(4) 0.0053(4) -0.0089(4) F1 0.0435(5) 0.0347(4) 0.0238(4) -0.0112(3) -0.0033(3) -0.0174(4) F2 0.0396(4) 0.0327(4) 0.0253(4) -0.0124(3) -0.0054(3) -0.0103(3) C8 0.0285(6) 0.0230(6) 0.0161(5) -0.0056(4) 0.0002(4) -0.0095(5) C9 0.0293(6) 0.0200(5) 0.0196(5) -0.0060(4) -0.0001(4) -0.0108(5) C10 0.0196(5) 0.0189(5) 0.0179(5) -0.0030(4) 0.0008(4) -0.0070(4) C11 0.0264(6) 0.0201(6) 0.0177(5) -0.0028(4) 0.0000(4) -0.0091(5) C12 0.0302(6) 0.0193(6) 0.0230(6) -0.0065(5) 0.0005(5) -0.0096(5) C13 0.0306(6) 0.0256(6) 0.0165(5) -0.0035(5) -0.0021(4) -0.0120(5) N1 0.0280(5) 0.0193(5) 0.0199(5) -0.0016(4) -0.0011(4) -0.0086(4) N2 0.0421(6) 0.0183(5) 0.0181(5) -0.0031(4) 0.0053(4) -0.0090(5) O3 0.0508(6) 0.0221(4) 0.0167(4) -0.0039(3) 0.0020(4) -0.0126(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 C1 C3 1.3928(16) . ? C1 C4 1.3940(16) . ? C1 C2 1.5093(16) . ? C2 O2 1.2166(15) . ? C2 O1 1.2948(14) . ? C3 F1 1.3432(14) . ? C3 C6 1.3832(18) . ? C4 F2 1.3484(14) . ? C4 C5 1.3820(18) . ? C5 C7 1.381(2) . ? C5 H5 0.905(18) . ? C6 C7 1.385(2) . ? C6 H6 0.941(18) . ? C7 H7 1.009(19) . ? O1 H1 0.8400 . ? C8 C12 1.3812(17) . ? C8 C10 1.3886(16) . ? C8 H8 0.928(15) . ? C9 C13 1.3838(17) . ? C9 C10 1.3936(16) . ? C9 H9 0.914(15) . ? C10 C11 1.5099(15) . ? C11 O3 1.2359(14) . ? C11 N2 1.3248(15) . ? C12 N1 1.3445(16) . ? C12 H12 0.955(16) . ? C13 N1 1.3325(16) . ? C13 H13 0.957(16) . ? N2 H2A 0.892(18) . ? N2 H2B 0.866(18) . ? 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 C3 C1 C4 115.09(11) . . ? C3 C1 C2 122.25(10) . . ? C4 C1 C2 122.66(10) . . ? O2 C2 O1 124.98(11) . . ? O2 C2 C1 122.23(10) . . ? O1 C2 C1 112.79(10) . . ? F1 C3 C6 117.36(11) . . ? F1 C3 C1 118.82(11) . . ? C6 C3 C1 123.76(11) . . ? F2 C4 C5 117.98(11) . . ? F2 C4 C1 118.54(10) . . ? C5 C4 C1 123.45(12) . . ? C7 C5 C4 118.60(12) . . ? C7 C5 H5 121.9(11) . . ? C4 C5 H5 119.5(11) . . ? C3 C6 C7 118.17(12) . . ? C3 C6 H6 118.7(10) . . ? C7 C6 H6 123.1(10) . . ? C5 C7 C6 120.94(12) . . ? C5 C7 H7 119.5(11) . . ? C6 C7 H7 119.5(11) . . ? C2 O1 H1 109.5 . . ? C12 C8 C10 118.97(11) . . ? C12 C8 H8 119.1(9) . . ? C10 C8 H8 121.9(9) . . ? C13 C9 C10 118.44(11) . . ? C13 C9 H9 118.0(9) . . ? C10 C9 H9 123.5(9) . . ? C8 C10 C9 118.80(10) . . ? C8 C10 C11 118.19(10) . . ? C9 C10 C11 122.96(10) . . ? O3 C11 N2 123.45(11) . . ? O3 C11 C10 118.85(10) . . ? N2 C11 C10 117.68(10) . . ? N1 C12 C8 122.22(11) . . ? N1 C12 H12 116.3(9) . . ? C8 C12 H12 121.5(9) . . ? N1 C13 C9 122.82(11) . . ? N1 C13 H13 116.1(9) . . ? C9 C13 H13 121.1(9) . . ? C13 N1 C12 118.73(10) . . ? C11 N2 H2A 118.4(11) . . ? C11 N2 H2B 124.3(11) . . ? H2A N2 H2B 116.6(15) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.331 _refine_diff_density_min -0.210 _refine_diff_density_rms 0.044 _database_code_depnum_ccdc_archive 'CCDC 965668' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_datam _audit_creation_date 2013-09-18 _audit_creation_method ; Olex2 1.2 (compiled Apr 23 2013 17:54:37, GUI svn.r4466) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C6 H6 N2 O, C7 H3 F3 O2' _chemical_formula_sum 'C13 H9 F3 N2 O3 ' _chemical_formula_weight 298.22 _chemical_melting_point ? 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' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.8789(12) _cell_length_b 7.2488(13) _cell_length_c 13.638(3) _cell_angle_alpha 89.962(6) _cell_angle_beta 81.279(7) _cell_angle_gamma 66.888(8) _cell_volume 616.95(19) _cell_formula_units_Z 2 _cell_measurement_reflns_used 5444 _cell_measurement_temperature 150 _cell_measurement_theta_max 27.7 _cell_measurement_theta_min 3.0 _exptl_absorpt_coefficient_mu 0.145 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.823 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_crystal_colour Colorless _exptl_crystal_density_diffrn 1.605 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description Prism _exptl_crystal_F_000 304 _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.12 _exptl_special_details ; ? ; _exptl_transmission_factor_max ? _exptl_transmission_factor_min ? _diffrn_reflns_av_R_equivalents 0.0364 _diffrn_reflns_av_unetI/netI 0.0422 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 6576 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.469 _diffrn_reflns_theta_min 3.029 _diffrn_ambient_temperature 150 _diffrn_detector CCD _diffrn_detector_area_resol_mean 13.6612 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_details ; scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 0.0000 XTD: 49.4000 2theta: 29.6000 scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 120.0000 XTD: 49.4000 2theta: 29.6000 scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 240.0000 XTD: 49.4000 2theta: 29.6000 ; _diffrn_measurement_device ; XtaLABmini: Fixed Chi 2 circle ; _diffrn_measurement_device_type ; Rigaku Mercury375R (2x2 bin mode) ; _diffrn_measurement_method 'profile data from \w-scans' _diffrn_measurement_specimen_support Fiber _diffrn_orient_matrix_type FS_PROCESS _diffrn_orient_matrix_UB_11 -0.138147 _diffrn_orient_matrix_UB_12 0.025189 _diffrn_orient_matrix_UB_13 -0.023877 _diffrn_orient_matrix_UB_21 0.012553 _diffrn_orient_matrix_UB_22 0.114734 _diffrn_orient_matrix_UB_23 -0.037269 _diffrn_orient_matrix_UB_31 0.080222 _diffrn_orient_matrix_UB_32 -0.093778 _diffrn_orient_matrix_UB_33 -0.059723 _diffrn_radiation_monochromator 'Graphite Monochromator' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_source 'Sealed Tube' _diffrn_source_current 12.0 _diffrn_source_power 0.6 _diffrn_source_voltage 50.0 _diffrn_special_details ; ? ; _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 2053 _reflns_number_total 2820 _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _reflns_threshold_expression 'I > 2\s(I)' _computing_cell_refinement ; CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009) ; _computing_data_collection ; CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ? _refine_diff_density_max 0.344 _refine_diff_density_min -0.281 _refine_diff_density_rms 0.059 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 226 _refine_ls_number_reflns 2820 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0730 _refine_ls_R_factor_gt 0.0488 _refine_ls_restrained_S_all 1.072 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.0516P)^2^+0.3204P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1155 _refine_ls_wR_factor_ref 0.1294 _refine_special_details ; ? ; _olex2_refinement_description ; ; _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary ? _atom_sites_solution_secondary ? 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group H10 H 0.054(3) 0.379(3) 0.7890(16) 0.019(5) Uiso 1 1 d . . . . . H2A H -0.075(4) 0.853(4) 0.4369(19) 0.034(7) Uiso 1 1 d . . . . . H2B H -0.315(4) 0.966(4) 0.4455(18) 0.028(6) Uiso 1 1 d . . . . . H3 H 0.651(4) -0.050(4) 0.9221(17) 0.029(6) Uiso 1 1 d . . . . . H11 H -0.231(4) 0.587(3) 0.7096(17) 0.027(6) Uiso 1 1 d . . . . . H13 H 0.461(4) 0.514(4) 0.5980(18) 0.030(6) Uiso 1 1 d . . . . . H12 H 0.188(4) 0.715(4) 0.5170(19) 0.034(7) Uiso 1 1 d . . . . . H5 H 1.187(4) -0.045(4) 0.7504(19) 0.030(6) Uiso 1 1 d . . . . . H1 H 0.454(6) 0.293(6) 0.754(3) 0.098(13) Uiso 1 1 d . . . . . C1 C 0.7600(3) 0.1165(3) 0.75881(15) 0.0226(4) Uani 1 1 d . . . . . C2 C 1.2403(3) -0.2113(3) 0.86857(17) 0.0274(5) Uani 1 1 d . . . . . C3 C 0.8009(3) -0.0872(3) 0.90847(16) 0.0238(5) Uani 1 1 d . . . . . C4 C 0.8973(3) -0.0225(3) 0.82568(15) 0.0212(4) Uani 1 1 d . . . . . C5 C 1.1190(3) -0.0857(3) 0.80545(16) 0.0246(5) Uani 1 1 d . . . . . C6 C 1.1479(3) -0.2762(3) 0.95053(16) 0.0274(5) Uani 1 1 d . . . . . C7 C 0.9288(4) -0.2136(3) 0.96909(15) 0.0260(5) Uani 1 1 d . . . . . O1 O 0.5566(2) 0.1848(3) 0.79527(12) 0.0359(4) Uani 1 1 d . . . . . O2 O 0.8339(2) 0.1594(2) 0.67956(11) 0.0300(4) Uani 1 1 d . . . . . F1 F 0.8404(2) -0.2771(2) 1.04994(10) 0.0381(4) Uani 1 1 d . . . . . F2 F 1.2678(2) -0.3948(2) 1.01293(11) 0.0411(4) Uani 1 1 d . . . . . F3 F 1.4545(2) -0.2737(2) 0.85203(11) 0.0441(4) Uani 1 1 d . . . . . C8 C -0.0526(3) 0.6766(3) 0.60296(14) 0.0203(4) Uani 1 1 d . . . . . C9 C -0.2431(3) 0.8112(3) 0.55835(15) 0.0215(4) Uani 1 1 d . . . . . C10 C 0.0787(3) 0.4522(3) 0.72772(16) 0.0254(5) Uani 1 1 d . . . . . C11 C -0.0917(3) 0.5751(3) 0.68463(15) 0.0224(4) Uani 1 1 d . . . . . C12 C 0.1572(3) 0.6531(3) 0.56911(16) 0.0235(4) Uani 1 1 d . . . . . C13 C 0.3175(3) 0.5296(3) 0.61721(16) 0.0262(5) Uani 1 1 d . . . . . N1 N 0.2805(3) 0.4287(3) 0.69547(13) 0.0250(4) Uani 1 1 d . . . . . N2 N -0.2065(3) 0.8876(3) 0.47217(14) 0.0244(4) Uani 1 1 d . . . . . O3 O -0.4248(2) 0.8452(2) 0.60270(12) 0.0323(4) Uani 1 1 d . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0236(10) 0.0239(11) 0.0196(10) 0.0020(8) -0.0026(8) -0.0091(8) C2 0.0177(10) 0.0277(12) 0.0329(12) -0.0025(9) -0.0049(9) -0.0048(8) C3 0.0194(10) 0.0275(11) 0.0225(10) 0.0012(9) -0.0033(8) -0.0072(8) C4 0.0216(10) 0.0219(10) 0.0193(10) 0.0005(8) -0.0041(8) -0.0075(8) C5 0.0238(11) 0.0271(11) 0.0220(11) 0.0004(9) -0.0010(9) -0.0103(9) C6 0.0307(11) 0.0229(11) 0.0266(11) 0.0025(9) -0.0135(9) -0.0052(9) C7 0.0316(11) 0.0270(11) 0.0202(10) 0.0044(9) -0.0045(9) -0.0124(9) O1 0.0198(8) 0.0499(11) 0.0274(8) 0.0160(8) -0.0043(7) -0.0026(7) O2 0.0306(8) 0.0351(9) 0.0255(8) 0.0103(7) -0.0034(7) -0.0148(7) F1 0.0442(8) 0.0473(9) 0.0267(7) 0.0182(6) -0.0081(6) -0.0214(7) F2 0.0394(8) 0.0379(8) 0.0424(9) 0.0134(7) -0.0224(7) -0.0060(6) F3 0.0190(7) 0.0565(10) 0.0500(9) 0.0084(7) -0.0080(6) -0.0071(6) C8 0.0207(10) 0.0192(10) 0.0186(10) 0.0018(8) -0.0036(8) -0.0053(8) C9 0.0224(10) 0.0206(10) 0.0206(10) 0.0036(8) -0.0045(8) -0.0075(8) C10 0.0295(11) 0.0262(11) 0.0203(10) 0.0051(9) -0.0064(9) -0.0100(9) C11 0.0209(10) 0.0247(11) 0.0202(10) 0.0038(8) -0.0035(8) -0.0076(8) C12 0.0247(11) 0.0253(11) 0.0216(10) 0.0061(9) -0.0037(9) -0.0111(9) C13 0.0206(10) 0.0298(12) 0.0268(11) 0.0028(9) -0.0043(9) -0.0083(9) N1 0.0239(9) 0.0254(9) 0.0232(9) 0.0033(7) -0.0082(7) -0.0057(7) N2 0.0181(9) 0.0278(10) 0.0231(9) 0.0097(8) -0.0048(8) -0.0043(7) O3 0.0182(7) 0.0415(10) 0.0308(8) 0.0180(7) -0.0035(6) -0.0054(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 C4 1.501(3) . ? C1 O1 1.302(2) . ? C1 O2 1.217(2) . ? C2 C5 1.374(3) . ? C2 C6 1.376(3) . ? C2 F3 1.343(2) . ? C3 H3 0.95(2) . ? C3 C4 1.397(3) . ? C3 C7 1.372(3) . ? C4 C5 1.391(3) . ? C5 H5 0.94(2) . ? C6 C7 1.375(3) . ? C6 F2 1.341(2) . ? C7 F1 1.346(2) . ? O1 H1 1.06(4) . ? C8 C9 1.509(3) . ? C8 C11 1.385(3) . ? C8 C12 1.389(3) . ? C9 N2 1.331(3) . ? C9 O3 1.232(2) . ? C10 H10 1.02(2) . ? C10 C11 1.379(3) . ? C10 N1 1.334(3) . ? C11 H11 0.94(2) . ? C12 H12 0.88(3) . ? C12 C13 1.375(3) . ? C13 H13 0.94(2) . ? C13 N1 1.342(3) . ? N2 H2A 0.90(3) . ? N2 H2B 0.87(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C4 112.66(17) . . ? O2 C1 C4 122.75(18) . . ? O2 C1 O1 124.59(19) . . ? C5 C2 C6 121.64(19) . . ? F3 C2 C5 120.5(2) . . ? F3 C2 C6 117.9(2) . . ? C4 C3 H3 121.7(15) . . ? C7 C3 H3 119.5(15) . . ? C7 C3 C4 118.79(19) . . ? C3 C4 C1 119.52(18) . . ? C5 C4 C1 120.17(19) . . ? C5 C4 C3 120.32(19) . . ? C2 C5 H5 119.3(15) . . ? C2 C5 C4 118.8(2) . . ? C4 C5 H5 121.9(15) . . ? C7 C6 C2 118.8(2) . . ? F2 C6 C2 121.0(2) . . ? F2 C6 C7 120.1(2) . . ? C3 C7 C6 121.6(2) . . ? F1 C7 C3 120.17(19) . . ? F1 C7 C6 118.24(19) . . ? C1 O1 H1 116(2) . . ? C11 C8 C9 117.45(18) . . ? C11 C8 C12 118.32(19) . . ? C12 C8 C9 124.20(18) . . ? N2 C9 C8 118.12(18) . . ? O3 C9 C8 118.97(18) . . ? O3 C9 N2 122.90(19) . . ? C11 C10 H10 120.4(12) . . ? N1 C10 H10 116.6(12) . . ? N1 C10 C11 122.99(19) . . ? C8 C11 H11 121.0(14) . . ? C10 C11 H11 120.0(14) . . ? C10 C11 C8 118.95(19) . . ? C8 C12 H12 120.8(16) . . ? C13 C12 H12 120.1(16) . . ? C13 C12 C8 119.0(2) . . ? C12 C13 H13 121.5(15) . . ? N1 C13 H13 115.7(15) . . ? N1 C13 C12 122.8(2) . . ? C10 N1 C13 117.94(18) . . ? H2A N2 H2B 118(2) . . ? C9 N2 H2A 122.7(16) . . ? C9 N2 H2B 119.4(15) . . ? _shelx_estimated_absorpt_T_max 0.983 _shelx_estimated_absorpt_T_min 0.958 _shelx_hkl_checksum 76774 _shelx_hkl_file ; 0 0 2 0.72 0.03 0 0 -2 0.57 0.02 0 0 3 9.50 0.15 0 0 3 9.36 0.17 0 0 -3 9.15 0.13 0 0 4 0.57 0.06 0 0 4 0.61 0.06 0 0 -4 0.60 0.04 0 0 5 19.71 0.38 0 0 5 19.35 0.36 0 0 -5 20.00 0.31 0 0 6 1.01 0.08 0 0 6 1.36 0.09 0 0 -6 1.08 0.06 0 0 7 9.67 0.27 0 0 7 9.03 0.27 0 0 -7 9.04 0.20 0 0 8 13.56 0.38 0 0 8 14.48 0.41 0 0 -8 12.98 0.32 0 0 9 1.77 0.14 0 0 9 1.73 0.14 0 0 -9 1.63 0.11 0 0 10 1.38 0.15 0 0 10 1.47 0.17 0 0 -10 1.33 0.09 0 0 11 6.20 0.30 0 0 11 6.35 0.29 0 0 -11 6.17 0.24 0 0 12 1.46 0.18 0 0 12 1.75 0.16 0 0 -12 1.38 0.13 0 0 13 1.30 0.17 0 0 -13 0.66 0.11 0 0 14 4.09 0.31 0 0 -14 3.75 0.22 0 0 -14 4.04 0.33 0 0 15 0.25 0.14 0 0 -15 0.09 0.10 0 0 -15 0.33 0.13 0 0 16 1.09 0.22 0 0 -16 0.68 0.18 0 0 17 1.28 0.29 0 0 -17 1.57 0.23 0 1 -17 -0.02 0.13 0 1 -16 0.01 0.09 0 -1 16 0.12 0.12 0 1 -15 0.11 0.07 0 -1 15 -0.07 0.11 0 1 -14 0.54 0.11 0 -1 14 0.40 0.11 0 -1 14 0.54 0.15 0 1 -13 0.23 0.09 0 -1 13 0.37 0.12 0 -1 13 0.33 0.13 0 1 -12 0.92 0.12 0 -1 12 1.18 0.16 0 -1 12 1.03 0.15 0 1 -11 0.05 0.07 0 -1 11 0.09 0.07 0 -1 11 0.16 0.09 0 1 -10 0.17 0.06 0 -1 10 0.17 0.08 0 -1 10 0.30 0.09 0 1 -9 1.45 0.11 0 -1 9 1.24 0.17 0 -1 9 1.51 0.11 0 1 -8 8.37 0.23 0 -1 8 8.07 0.29 0 -1 8 8.30 0.24 0 1 -7 69.99 1.15 0 -1 7 67.39 1.13 0 -1 7 69.36 1.33 0 1 -6 5.35 0.15 0 -1 6 5.73 0.15 0 -1 6 6.44 0.21 0 1 -5 7.61 0.16 0 -1 5 7.42 0.16 0 -1 5 7.86 0.22 0 1 -4 47.28 0.63 0 -1 4 47.17 0.70 0 -1 4 47.14 0.58 0 1 -3 0.13 0.03 0 -1 3 0.36 0.04 0 -1 2 0.19 0.02 0 -1 2 0.19 0.02 0 -1 1 4.16 0.06 0 -1 1 3.01 0.06 0 -1 0 0.00 0.01 0 -1 0 0.01 0.01 0 1 1 1.51 0.05 0 1 1 1.39 0.02 0 -1 -1 1.18 0.04 0 -1 -1 1.30 0.02 0 1 2 2.16 0.08 0 -1 -2 2.20 0.05 0 -1 -2 2.12 0.04 0 1 3 461.55 5.71 0 -1 -3 460.39 4.24 0 -1 -3 461.23 4.72 0 1 4 20.76 0.41 0 -1 -4 20.29 0.30 0 -1 -4 20.32 0.32 0 1 5 18.18 0.41 0 -1 -5 17.94 0.32 0 -1 -5 17.87 0.33 0 1 6 1.33 0.11 0 -1 -6 1.26 0.08 0 -1 -6 1.38 0.08 0 -1 -7 0.52 0.07 0 -1 -7 0.69 0.08 0 1 8 29.66 0.75 0 -1 -8 29.84 0.63 0 -1 -8 30.90 0.68 0 1 9 0.88 0.14 0 -1 -9 1.15 0.12 0 -1 -9 1.11 0.10 0 1 10 1.07 0.17 0 -1 -10 0.83 0.11 0 -1 -10 1.06 0.13 0 1 11 2.27 0.20 0 -1 -11 1.83 0.14 0 -1 -11 1.80 0.18 0 1 12 0.05 0.14 0 -1 -12 0.14 0.09 0 -1 -12 0.34 0.11 0 1 13 -0.13 0.12 0 -1 -13 0.07 0.08 0 -1 -13 0.11 0.08 0 1 14 2.20 0.22 0 -1 -14 2.01 0.23 0 -1 -14 1.73 0.17 0 1 15 0.12 0.14 0 -1 -15 -0.03 0.11 0 1 16 0.99 0.21 0 -1 -16 1.29 0.23 0 1 17 0.63 0.18 0 -1 -17 0.35 0.18 0 -2 17 -0.05 0.17 0 -2 16 0.42 0.23 0 2 -15 -0.05 0.07 0 -2 15 0.04 0.11 0 -2 15 0.14 0.09 0 2 -14 -0.07 0.07 0 -2 14 0.14 0.12 0 -2 14 0.13 0.08 0 2 -13 1.00 0.13 0 -2 13 0.80 0.12 0 -2 13 0.85 0.17 0 2 -12 17.04 0.54 0 -2 12 18.46 0.55 0 -2 12 18.37 0.71 0 2 -11 23.63 0.61 0 -2 11 25.90 0.66 0 -2 11 25.26 0.81 0 2 -10 5.37 0.22 0 -2 10 5.55 0.30 0 -2 10 5.69 0.21 0 2 -9 0.00 0.05 0 -2 9 -0.13 0.08 0 -2 9 0.06 0.05 0 2 -8 21.74 0.51 0 -2 8 21.27 0.45 0 -2 8 21.19 0.58 0 2 -7 1.06 0.09 0 -2 7 1.09 0.10 0 -2 7 1.24 0.07 0 2 -6 7.48 0.20 0 -2 6 7.15 0.24 0 -2 6 7.34 0.17 0 2 -5 1.61 0.09 0 -2 5 1.77 0.07 0 2 -4 17.03 0.35 0 -2 4 17.19 0.27 0 -2 4 17.23 0.36 0 -2 3 14.55 0.21 0 -2 3 14.90 0.29 0 -2 3 15.15 0.29 0 2 -2 2.07 0.06 0 -2 2 1.96 0.08 0 2 -1 34.03 0.50 0 -2 1 34.13 0.43 0 -2 1 33.79 0.51 0 2 0 30.50 0.49 0 -2 0 29.63 0.34 0 -2 0 31.15 0.49 0 2 1 10.37 0.24 0 -2 -1 10.02 0.21 0 2 2 112.58 1.74 0 -2 -2 110.01 1.06 0 -2 -2 111.69 1.54 0 2 3 0.31 0.07 0 -2 -3 0.45 0.03 0 -2 -3 0.46 0.05 0 2 4 0.68 0.08 0 -2 -4 0.59 0.06 0 2 5 7.28 0.24 0 -2 -5 6.73 0.19 0 -2 -5 7.09 0.16 0 2 6 0.65 0.12 0 -2 -6 1.07 0.08 0 -2 -6 0.95 0.06 0 2 7 0.20 0.09 0 -2 -7 0.23 0.05 0 -2 -7 0.23 0.05 0 2 8 2.84 0.20 0 -2 -8 3.06 0.15 0 -2 -8 2.99 0.14 0 2 9 0.18 0.11 0 -2 -9 0.12 0.06 0 -2 -9 0.16 0.06 0 2 10 12.69 0.48 0 -2 -10 12.30 0.40 0 -2 -10 12.44 0.41 0 2 11 5.96 0.34 0 -2 -11 5.26 0.25 0 -2 -11 5.74 0.27 0 2 12 0.82 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0.15 7 7 8 0.45 0.29 -7 -7 -8 0.61 0.19 7 8 -1 0.09 0.18 7 8 0 1.98 0.34 -7 -8 0 0.88 0.22 7 8 1 2.52 0.33 -7 -8 -1 1.88 0.23 7 8 2 0.08 0.21 -7 -8 -2 0.54 0.15 7 8 3 1.55 0.30 -7 -8 -3 1.09 0.21 7 8 4 1.24 0.32 -7 -8 -4 1.32 0.25 8 0 -1 0.13 0.15 8 0 0 1.07 0.27 8 0 1 0.82 0.21 8 0 2 -0.18 0.14 8 0 3 0.59 0.23 8 0 4 2.71 0.35 -8 0 -4 2.29 0.27 8 0 5 0.45 0.17 -8 0 -5 0.37 0.18 8 0 6 0.52 0.24 -8 0 -6 0.51 0.20 8 1 -3 0.09 0.13 -8 -1 3 -0.14 0.12 8 1 -2 0.24 0.20 -8 -1 2 0.50 0.18 8 1 -1 0.00 0.16 -8 -1 1 0.40 0.12 8 1 0 0.39 0.17 -8 -1 0 0.26 0.15 8 1 1 0.98 0.18 -8 -1 -1 0.58 0.16 8 1 2 0.34 0.16 8 1 3 0.74 0.22 -8 -1 -3 0.66 0.15 8 1 4 0.19 0.15 -8 -1 -4 0.35 0.14 8 1 5 0.09 0.10 -8 -1 -5 -0.08 0.09 8 1 6 1.92 0.30 -8 -1 -6 1.81 0.22 8 1 7 2.61 0.35 -8 -1 -7 3.01 0.27 8 1 8 0.92 0.25 -8 -1 -8 0.93 0.23 8 2 -4 0.75 0.18 -8 -2 4 0.42 0.22 8 2 -3 -0.05 0.15 -8 -2 3 -0.03 0.14 8 2 -2 0.17 0.13 -8 -2 2 0.14 0.15 8 2 -1 0.20 0.16 -8 -2 1 0.06 0.14 8 2 0 0.21 0.13 -8 -2 0 -0.05 0.12 8 2 1 0.31 0.16 -8 -2 -1 0.54 0.13 8 2 2 0.10 0.14 -8 -2 -2 0.11 0.09 8 2 3 1.10 0.18 -8 -2 -3 1.17 0.17 -8 -2 -3 0.91 0.17 8 2 4 0.32 0.13 -8 -2 -4 0.24 0.14 8 2 5 1.56 0.21 -8 -2 -5 1.66 0.22 8 2 6 0.01 0.11 -8 -2 -6 0.06 0.10 8 2 7 3.07 0.34 -8 -2 -7 2.94 0.28 8 2 8 0.55 0.17 -8 -2 -8 0.64 0.17 8 2 9 0.56 0.18 -8 -2 -9 0.83 0.24 8 3 -5 -0.04 0.15 -8 -3 5 0.03 0.12 8 3 -4 0.21 0.15 -8 -3 4 0.27 0.14 8 3 -3 1.10 0.18 -8 -3 3 0.88 0.20 8 3 -2 0.12 0.13 -8 -3 2 0.16 0.12 8 3 -1 0.08 0.09 -8 -3 1 -0.08 0.09 8 3 0 2.51 0.24 -8 -3 0 2.94 0.25 8 3 1 0.98 0.21 -8 -3 -1 0.97 0.20 8 3 2 0.28 0.14 -8 -3 -2 0.03 0.13 8 3 3 1.30 0.22 -8 -3 -3 1.03 0.19 -8 -3 -3 1.57 0.19 8 3 4 0.09 0.14 -8 -3 -4 0.02 0.09 -8 -3 -4 0.25 0.12 8 3 5 0.24 0.12 -8 -3 -5 0.38 0.12 8 3 6 0.86 0.18 -8 -3 -6 0.63 0.16 8 3 7 0.43 0.16 -8 -3 -7 0.35 0.18 8 3 8 -0.12 0.10 -8 -3 -8 0.12 0.14 8 3 9 0.21 0.14 -8 -3 -9 0.47 0.19 8 3 10 0.27 0.19 -8 -3 -10 0.90 0.19 8 4 -5 0.34 0.17 -8 -4 5 0.45 0.17 8 4 -4 0.99 0.20 -8 -4 4 1.00 0.21 8 4 -3 1.29 0.26 -8 -4 3 1.83 0.24 8 4 -2 0.12 0.15 -8 -4 2 0.18 0.13 8 4 -1 1.11 0.23 -8 -4 1 1.53 0.20 8 4 0 -0.02 0.09 -8 -4 0 -0.02 0.10 8 4 1 0.06 0.09 -8 -4 -1 -0.02 0.10 8 4 2 0.54 0.14 -8 -4 -2 0.76 0.15 -8 -4 -2 0.62 0.15 8 4 3 0.17 0.14 -8 -4 -3 0.33 0.14 -8 -4 -3 0.22 0.13 8 4 4 0.67 0.14 -8 -4 -4 0.52 0.14 -8 -4 -4 0.63 0.19 8 4 5 0.17 0.08 8 4 5 -0.05 0.11 -8 -4 -5 -0.22 0.12 8 4 6 0.65 0.17 8 4 6 0.66 0.17 -8 -4 -6 0.87 0.20 8 4 7 0.05 0.12 8 4 7 -0.01 0.15 -8 -4 -7 0.15 0.14 -8 -4 -8 0.22 0.15 -8 -4 -9 -0.02 0.12 8 5 -4 0.04 0.14 -8 -5 4 0.30 0.15 8 5 -3 -0.01 0.14 -8 -5 3 0.17 0.13 8 5 -2 0.94 0.22 -8 -5 2 1.53 0.26 8 5 -1 0.07 0.11 -8 -5 1 0.16 0.12 8 5 0 0.27 0.12 -8 -5 0 -0.04 0.13 8 5 1 -0.10 0.09 -8 -5 -1 0.06 0.12 8 5 2 0.08 0.11 -8 -5 -2 -0.12 0.10 -8 -5 -2 -0.07 0.13 8 5 3 0.02 0.10 -8 -5 -3 0.10 0.12 -8 -5 -3 0.04 0.15 8 5 4 1.78 0.22 8 5 4 2.32 0.32 -8 -5 -4 1.58 0.20 8 5 5 0.80 0.24 -8 -5 -5 1.00 0.17 8 5 6 1.44 0.24 -8 -5 -6 1.00 0.24 8 5 7 1.90 0.35 -8 -5 -7 2.12 0.30 8 5 8 0.25 0.22 -8 -5 -8 0.21 0.19 -8 -5 -9 1.21 0.24 8 6 -3 -0.02 0.13 -8 -6 3 -0.11 0.14 8 6 -2 0.09 0.13 -8 -6 2 0.15 0.14 8 6 -1 2.66 0.27 -8 -6 1 3.23 0.34 -8 -6 0 0.03 0.13 -8 -6 -1 0.25 0.16 -8 -6 -2 1.15 0.19 8 6 3 0.38 0.19 -8 -6 -3 0.21 0.16 8 6 4 0.60 0.26 -8 -6 -4 0.56 0.20 8 6 5 0.26 0.22 -8 -6 -5 1.13 0.22 8 6 6 0.07 0.14 -8 -6 -6 -0.03 0.13 8 6 7 2.67 0.39 -8 -6 -7 1.62 0.32 -8 -7 0 -0.31 0.22 8 7 1 0.05 0.17 8 7 2 0.81 0.26 8 7 3 -0.04 0.21 -8 -7 -3 0.18 0.15 8 7 4 0.78 0.30 -8 -7 -4 0.70 0.19 0 0 0 0.00 0.00 ; _shelx_res_checksum 56999 _shelx_res_file ; TITL datam in P-1 CELL 0.71073 6.8789 7.2488 13.6384 89.962 81.279 66.888 ZERR 2 0.0012 0.0013 0.0025 0.006 0.007 0.008 LATT 1 SFAC C H N O F UNIT 26 18 4 6 6 L.S. 10 PLAN 20 SIZE 0.12 0.2 0.3 TEMP -123.15 BOND $H fmap 2 acta MERG 2 REM F:/Experimental%20DATA/Structural%20Landscape/Coformer%20Modification REM /IsoNicotinamide/Full%20data/345fbaIsoNicAmd_ETOH_2/345fbaIsoNicAmd_ETOH_2 REM /345fbaIsoNicAmd_ETOH_2/345fbaIsoNicAmd_ETOH_2/datam.hkl WGHT 0.051600 0.320400 FVAR 0.18721 H10 2 0.053548 0.379161 0.788955 11.00000 0.01854 H2A 2 -0.074874 0.852569 0.436896 11.00000 0.03351 H2B 2 -0.314638 0.966455 0.445474 11.00000 0.02764 H3 2 0.650948 -0.050406 0.922104 11.00000 0.02905 H11 2 -0.230509 0.586591 0.709626 11.00000 0.02702 H13 2 0.461054 0.513661 0.597989 11.00000 0.03033 H12 2 0.188274 0.715129 0.517031 11.00000 0.03424 H5 2 1.187359 -0.044775 0.750362 11.00000 0.02970 H1 2 0.454108 0.293476 0.754032 11.00000 0.09796 C1 1 0.759983 0.116503 0.758814 11.00000 0.02359 0.02386 = 0.01959 0.00195 -0.00263 -0.00909 C2 1 1.240255 -0.211301 0.868565 11.00000 0.01770 0.02772 = 0.03295 -0.00251 -0.00489 -0.00475 C3 1 0.800928 -0.087195 0.908467 11.00000 0.01939 0.02748 = 0.02247 0.00123 -0.00328 -0.00720 C4 1 0.897348 -0.022457 0.825676 11.00000 0.02155 0.02189 = 0.01928 0.00053 -0.00408 -0.00755 C5 1 1.118958 -0.085651 0.805448 11.00000 0.02380 0.02714 = 0.02198 0.00043 -0.00096 -0.01027 C6 1 1.147938 -0.276184 0.950533 11.00000 0.03068 0.02285 = 0.02658 0.00249 -0.01351 -0.00522 C7 1 0.928766 -0.213614 0.969094 11.00000 0.03159 0.02704 = 0.02021 0.00439 -0.00447 -0.01242 O1 4 0.556588 0.184810 0.795269 11.00000 0.01979 0.04991 = 0.02740 0.01597 -0.00431 -0.00261 O2 4 0.833882 0.159381 0.679558 11.00000 0.03064 0.03507 = 0.02546 0.01029 -0.00342 -0.01482 F1 5 0.840409 -0.277071 1.049943 11.00000 0.04415 0.04733 = 0.02668 0.01821 -0.00811 -0.02137 F2 5 1.267805 -0.394831 1.012934 11.00000 0.03941 0.03787 = 0.04243 0.01335 -0.02243 -0.00603 F3 5 1.454540 -0.273695 0.852031 11.00000 0.01902 0.05654 = 0.04995 0.00836 -0.00803 -0.00708 C8 1 -0.052610 0.676630 0.602962 11.00000 0.02071 0.01918 = 0.01856 0.00180 -0.00363 -0.00526 C9 1 -0.243095 0.811186 0.558347 11.00000 0.02245 0.02063 = 0.02061 0.00359 -0.00455 -0.00749 C10 1 0.078677 0.452161 0.727724 11.00000 0.02954 0.02618 = 0.02031 0.00510 -0.00640 -0.00998 C11 1 -0.091676 0.575144 0.684635 11.00000 0.02086 0.02468 = 0.02017 0.00375 -0.00351 -0.00756 C12 1 0.157198 0.653082 0.569114 11.00000 0.02467 0.02526 = 0.02163 0.00610 -0.00373 -0.01110 C13 1 0.317530 0.529577 0.617210 11.00000 0.02056 0.02982 = 0.02685 0.00284 -0.00434 -0.00830 N1 3 0.280471 0.428720 0.695474 11.00000 0.02388 0.02537 = 0.02320 0.00329 -0.00823 -0.00566 N2 3 -0.206485 0.887649 0.472165 11.00000 0.01809 0.02782 = 0.02311 0.00967 -0.00478 -0.00426 O3 4 -0.424799 0.845239 0.602704 11.00000 0.01819 0.04146 = 0.03079 0.01798 -0.00350 -0.00535 HKLF 4 REM datam in P-1 REM R1 = 0.0488 for 2053 Fo > 4sig(Fo) and 0.0730 for all 2820 data REM 226 parameters refined using 0 restraints END WGHT 0.0516 0.3204 REM Highest difference peak 0.344, deepest hole -0.281, 1-sigma level 0.059 Q1 1 0.8301 0.0620 0.7965 11.00000 0.05 0.34 Q2 1 -0.1417 0.7438 0.5766 11.00000 0.05 0.34 Q3 1 0.4839 0.2432 0.7602 11.00000 0.05 0.32 Q4 1 0.3732 0.3563 0.7168 11.00000 0.05 0.27 Q5 1 -0.0070 0.5315 0.7192 11.00000 0.05 0.27 Q6 1 -0.3077 0.6388 0.7428 11.00000 0.05 0.23 Q7 1 0.2332 0.5925 0.5978 11.00000 0.05 0.23 Q8 1 -0.5469 0.9194 0.5838 11.00000 0.05 0.22 Q9 1 0.1512 0.4746 0.6976 11.00000 0.05 0.22 Q10 1 0.9980 -0.3758 1.0731 11.00000 0.05 0.21 Q11 1 1.4006 -0.4841 1.0196 11.00000 0.05 0.21 Q12 1 1.1802 -0.1385 0.8458 11.00000 0.05 0.21 Q13 1 1.0342 -0.2144 0.9744 11.00000 0.05 0.21 Q14 1 0.8583 -0.1452 0.9435 11.00000 0.05 0.21 Q15 1 0.7138 0.2591 0.6597 11.00000 0.05 0.20 Q16 1 0.9018 0.2495 0.7019 11.00000 0.05 0.20 Q17 1 0.0869 0.5864 0.5616 11.00000 0.05 0.20 Q18 1 0.9717 0.1061 0.6436 11.00000 0.05 0.20 Q19 1 1.1949 -0.3273 0.9875 11.00000 0.05 0.20 Q20 1 0.5067 0.4125 0.5847 11.00000 0.05 0.19 ; _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelxl_version_number 2013-2 _database_code_depnum_ccdc_archive 'CCDC 965669' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_datam _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H9 F3 N2 O3' _chemical_formula_weight 298.22 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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.7191(14) _cell_length_b 10.869(2) _cell_length_c 15.312(3) _cell_angle_alpha 73.545(5) _cell_angle_beta 86.948(6) _cell_angle_gamma 85.853(6) _cell_volume 1228.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.613 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.145 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9577 _exptl_absorpt_correction_T_max 0.9856 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12973 _diffrn_reflns_av_R_equivalents 0.0895 _diffrn_reflns_av_sigmaI/netI 0.1163 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 27.48 _reflns_number_total 5593 _reflns_number_gt 2467 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0842P)^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_number_reflns 5593 _refine_ls_number_parameters 445 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1783 _refine_ls_R_factor_gt 0.0720 _refine_ls_wR_factor_ref 0.1993 _refine_ls_wR_factor_gt 0.1590 _refine_ls_goodness_of_fit_ref 0.985 _refine_ls_restrained_S_all 0.985 _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 C7 C 0.4516(5) 0.2878(4) 0.7253(3) 0.0259(9) Uani 1 1 d . . . C1 C 0.3850(5) 0.3567(4) 0.7932(3) 0.0242(9) Uani 1 1 d . . . C6 C 0.2513(5) 0.4533(4) 0.7712(3) 0.0262(9) Uani 1 1 d . . . C5 C 0.1929(5) 0.5132(4) 0.8356(3) 0.0303(10) Uani 1 1 d . . . C4 C 0.2587(5) 0.4799(4) 0.9209(3) 0.0290(10) Uani 1 1 d . . . C3 C 0.3913(5) 0.3843(4) 0.9421(3) 0.0288(10) Uani 1 1 d . . . C2 C 0.4551(5) 0.3231(4) 0.8796(3) 0.0252(9) Uani 1 1 d . . . C8 C 0.2078(5) 0.0330(3) 0.8545(3) 0.0243(9) Uani 1 1 d . . . C13 C 0.0779(5) 0.1318(4) 0.8309(3) 0.0281(10) Uani 1 1 d . . . C11 C 0.0899(5) 0.1624(4) 0.9793(3) 0.0299(10) Uani 1 1 d . . . C12 C 0.0192(5) 0.1930(4) 0.8948(3) 0.0291(10) Uani 1 1 d . . . C10 C 0.2181(5) 0.0654(4) 1.0009(3) 0.0276(9) Uani 1 1 d . . . C9 C 0.2770(5) 0.0002(4) 0.9404(3) 0.0277(10) Uani 1 1 d . . . C14 C 0.2740(5) -0.0373(4) 0.7869(3) 0.0255(9) Uani 1 1 d . . . C17 C -0.1376(5) -0.1165(3) 0.5701(2) 0.0213(9) Uani 1 1 d . . . C16 C -0.2583(5) -0.0207(4) 0.5270(3) 0.0287(10) Uani 1 1 d . . . C15 C -0.3380(5) 0.0601(4) 0.5744(3) 0.0289(10) Uani 1 1 d . . . C19 C -0.1893(5) -0.0430(4) 0.7020(3) 0.0308(10) Uani 1 1 d . . . C18 C -0.1040(6) -0.1261(4) 0.6589(3) 0.0259(10) Uani 1 1 d . . . C20 C -0.0443(5) -0.2103(4) 0.5264(3) 0.0241(9) Uani 1 1 d . . . C26 C -0.2121(5) -0.5335(4) 0.5920(3) 0.0246(9) Uani 1 1 d . . . C23 C -0.3151(5) -0.4428(3) 0.6358(3) 0.0223(9) Uani 1 1 d . . . C22 C -0.4512(5) -0.3605(4) 0.5961(3) 0.0272(10) Uani 1 1 d . . . C21 C -0.5390(6) -0.2840(4) 0.6437(3) 0.0280(10) Uani 1 1 d . . . C25 C -0.3597(5) -0.3608(4) 0.7641(3) 0.0295(10) Uani 1 1 d . . . C24 C -0.2697(5) -0.4431(4) 0.7222(3) 0.0259(10) Uani 1 1 d . . . N1 N -0.3051(4) 0.0490(3) 0.6617(2) 0.0277(8) Uani 1 1 d . . . N2 N -0.0743(5) -0.2008(4) 0.4394(2) 0.0288(9) Uani 1 1 d . . . N3 N -0.4929(4) -0.2822(3) 0.7265(2) 0.0280(8) Uani 1 1 d . . . N4 N -0.2283(5) -0.5125(4) 0.5027(2) 0.0285(9) Uani 1 1 d . . . O3 O 0.2377(4) -0.0021(3) 0.70710(18) 0.0363(8) Uani 1 1 d . . . O1 O 0.4095(4) 0.3197(3) 0.64651(18) 0.0362(7) Uani 1 1 d . . . O4 O 0.3717(4) -0.1393(3) 0.82413(18) 0.0403(8) Uani 1 1 d . . . H1 H 0.4125 -0.1729 0.7837 0.060 Uiso 1 1 calc R . . O5 O 0.0580(3) -0.2947(3) 0.57233(18) 0.0310(7) Uani 1 1 d . . . O2 O 0.5571(4) 0.1894(3) 0.76112(18) 0.0333(7) Uani 1 1 d . . . H2 H 0.5907 0.1526 0.7213 0.050 Uiso 1 1 calc R . . O6 O -0.1208(4) -0.6218(3) 0.63877(18) 0.0354(8) Uani 1 1 d . . . F1 F 0.4543(3) 0.3528(2) 1.02593(15) 0.0447(7) Uani 1 1 d . . . F4 F 0.2853(3) 0.0381(2) 1.08369(15) 0.0443(7) Uani 1 1 d . . . F5 F 0.0334(3) 0.2251(2) 1.04027(16) 0.0442(7) Uani 1 1 d . . . F6 F -0.1074(3) 0.2871(2) 0.87537(17) 0.0463(7) Uani 1 1 d . . . F2 F 0.1974(3) 0.5384(2) 0.98313(16) 0.0449(7) Uani 1 1 d . . . F3 F 0.0657(3) 0.6074(2) 0.81649(17) 0.0449(7) Uani 1 1 d . . . H3 H -0.189(5) -0.562(4) 0.485(3) 0.019(13) Uiso 1 1 d . . . H4 H -0.295(6) -0.442(4) 0.466(3) 0.056(15) Uiso 1 1 d . . . H5 H -0.485(4) -0.363(3) 0.541(2) 0.009(9) Uiso 1 1 d . . . H6 H -0.627(5) -0.225(4) 0.619(2) 0.028(11) Uiso 1 1 d . . . H7 H -0.181(5) -0.492(4) 0.749(3) 0.034(12) Uiso 1 1 d . . . H8 H -0.317(5) -0.351(4) 0.821(3) 0.053(14) Uiso 1 1 d . . . H9 H -0.009(5) -0.256(4) 0.417(3) 0.035(12) Uiso 1 1 d . . . H10 H -0.161(7) -0.151(5) 0.421(4) 0.08(2) Uiso 1 1 d . . . H11 H -0.297(5) -0.003(4) 0.469(3) 0.044(13) Uiso 1 1 d . . . H12 H -0.437(5) 0.120(4) 0.550(3) 0.038(12) Uiso 1 1 d . . . H13 H -0.039(5) -0.187(4) 0.691(3) 0.049(15) Uiso 1 1 d . . . H14 H -0.177(5) -0.048(4) 0.766(3) 0.034(11) Uiso 1 1 d . . . H15 H 0.377(6) -0.062(4) 0.954(3) 0.058(14) Uiso 1 1 d . . . H16 H 0.024(5) 0.158(4) 0.773(3) 0.040(12) Uiso 1 1 d . . . H17 H 0.192(5) 0.477(4) 0.712(3) 0.057(14) Uiso 1 1 d . . . H18 H 0.555(5) 0.254(4) 0.888(3) 0.042(12) 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 C7 0.029(2) 0.027(2) 0.022(2) -0.0065(19) 0.0023(18) -0.0019(19) C1 0.024(2) 0.022(2) 0.027(2) -0.0066(18) 0.0006(17) -0.0012(17) C6 0.026(2) 0.025(2) 0.026(2) -0.0042(19) -0.0051(18) -0.0001(18) C5 0.030(2) 0.023(2) 0.038(3) -0.009(2) -0.005(2) 0.0072(18) C4 0.034(2) 0.030(2) 0.027(2) -0.015(2) 0.0057(19) -0.0014(19) C3 0.033(2) 0.031(2) 0.024(2) -0.009(2) -0.0013(19) -0.0015(19) C2 0.026(2) 0.025(2) 0.024(2) -0.0064(19) 0.0026(18) -0.0009(18) C8 0.024(2) 0.020(2) 0.026(2) -0.0034(18) 0.0030(18) -0.0008(17) C13 0.023(2) 0.029(2) 0.030(2) -0.006(2) -0.0007(19) 0.0029(18) C11 0.029(2) 0.027(2) 0.037(3) -0.015(2) 0.010(2) -0.0051(18) C12 0.021(2) 0.027(2) 0.038(3) -0.008(2) 0.0003(19) 0.0039(18) C10 0.027(2) 0.039(3) 0.019(2) -0.011(2) 0.0031(18) -0.0042(19) C9 0.030(2) 0.028(2) 0.024(2) -0.006(2) 0.0006(19) 0.002(2) C14 0.029(2) 0.025(2) 0.021(2) -0.0045(19) -0.0024(18) 0.0004(18) C17 0.019(2) 0.022(2) 0.021(2) -0.0045(18) -0.0021(17) -0.0026(17) C16 0.032(2) 0.029(2) 0.025(2) -0.008(2) -0.003(2) 0.0042(19) C15 0.026(2) 0.030(2) 0.031(2) -0.010(2) -0.0031(19) 0.0076(19) C19 0.035(3) 0.029(2) 0.028(2) -0.009(2) 0.005(2) 0.001(2) C18 0.032(2) 0.024(2) 0.022(2) -0.0066(19) -0.0017(19) 0.001(2) C20 0.025(2) 0.021(2) 0.026(2) -0.0055(18) 0.0033(18) -0.0029(18) C26 0.031(2) 0.019(2) 0.022(2) -0.0053(18) 0.0007(18) 0.0030(18) C23 0.025(2) 0.018(2) 0.025(2) -0.0061(18) 0.0013(17) -0.0018(17) C22 0.031(2) 0.024(2) 0.027(2) -0.011(2) 0.001(2) 0.0034(18) C21 0.033(3) 0.023(2) 0.027(2) -0.0063(19) -0.0006(19) 0.0018(19) C25 0.030(2) 0.036(3) 0.025(2) -0.014(2) -0.0020(19) -0.001(2) C24 0.026(2) 0.027(2) 0.025(2) -0.010(2) -0.0018(19) 0.0038(19) N1 0.031(2) 0.0262(19) 0.0251(19) -0.0082(16) 0.0073(16) 0.0036(15) N2 0.033(2) 0.029(2) 0.027(2) -0.0141(18) -0.0021(17) 0.0122(18) N3 0.0284(19) 0.0268(19) 0.0281(19) -0.0091(16) 0.0062(16) 0.0024(15) N4 0.035(2) 0.026(2) 0.024(2) -0.0096(19) -0.0009(17) 0.0112(18) O3 0.0417(18) 0.0421(18) 0.0261(16) -0.0131(15) -0.0073(14) 0.0106(14) O1 0.0466(19) 0.0386(18) 0.0233(16) -0.0091(14) -0.0070(14) 0.0036(14) O4 0.057(2) 0.0379(18) 0.0244(16) -0.0130(14) -0.0004(15) 0.0248(16) O5 0.0355(17) 0.0318(16) 0.0265(16) -0.0125(14) -0.0066(13) 0.0147(14) O2 0.0398(18) 0.0325(17) 0.0273(16) -0.0124(14) -0.0001(14) 0.0154(14) O6 0.0494(19) 0.0316(17) 0.0228(16) -0.0088(14) 0.0007(14) 0.0166(15) F1 0.0539(18) 0.0583(17) 0.0225(13) -0.0158(12) -0.0092(12) 0.0165(14) F4 0.0477(17) 0.0612(18) 0.0266(13) -0.0187(13) -0.0044(12) 0.0082(13) F5 0.0495(16) 0.0429(15) 0.0473(16) -0.0284(13) 0.0100(13) 0.0054(12) F6 0.0394(16) 0.0379(15) 0.0581(18) -0.0145(14) 0.0056(13) 0.0191(12) F2 0.0499(16) 0.0489(16) 0.0416(15) -0.0262(13) 0.0041(12) 0.0102(13) F3 0.0457(16) 0.0408(15) 0.0501(17) -0.0207(13) -0.0123(13) 0.0244(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 C7 O1 1.213(4) . ? C7 O2 1.303(4) . ? C7 C1 1.495(5) . ? C1 C2 1.396(5) . ? C1 C6 1.400(5) . ? C6 C5 1.369(5) . ? C6 H17 1.00(4) . ? C5 F3 1.347(4) . ? C5 C4 1.368(5) . ? C4 F2 1.337(4) . ? C4 C3 1.387(5) . ? C3 F1 1.339(4) . ? C3 C2 1.366(5) . ? C2 H18 1.02(4) . ? C8 C9 1.387(5) . ? C8 C13 1.397(5) . ? C8 C14 1.501(5) . ? C13 C12 1.372(5) . ? C13 H16 0.96(4) . ? C11 F5 1.341(4) . ? C11 C10 1.374(6) . ? C11 C12 1.374(5) . ? C12 F6 1.343(4) . ? C10 F4 1.341(4) . ? C10 C9 1.360(5) . ? C9 H15 0.98(4) . ? C14 O3 1.213(4) . ? C14 O4 1.300(4) . ? C17 C18 1.371(5) . ? C17 C16 1.387(5) . ? C17 C20 1.494(5) . ? C16 C15 1.383(5) . ? C16 H11 0.91(4) . ? C15 N1 1.344(5) . ? C15 H12 0.98(4) . ? C19 N1 1.327(5) . ? C19 C18 1.375(6) . ? C19 H14 0.97(4) . ? C18 H13 0.85(4) . ? C20 O5 1.244(4) . ? C20 N2 1.339(5) . ? C26 O6 1.224(4) . ? C26 N4 1.331(5) . ? C26 C23 1.502(5) . ? C23 C22 1.377(5) . ? C23 C24 1.386(5) . ? C22 C21 1.375(5) . ? C22 H5 0.90(3) . ? C21 N3 1.341(5) . ? C21 H6 0.92(4) . ? C25 N3 1.333(5) . ? C25 C24 1.371(5) . ? C25 H8 0.99(4) . ? C24 H7 0.88(4) . ? N2 H9 0.88(4) . ? N2 H10 0.84(5) . ? N4 H3 0.71(4) . ? N4 H4 0.94(5) . ? O4 H1 0.8400 . ? O2 H2 0.8400 . ? 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 C7 O2 124.4(4) . . ? O1 C7 C1 123.4(4) . . ? O2 C7 C1 112.2(3) . . ? C2 C1 C6 119.9(4) . . ? C2 C1 C7 119.6(4) . . ? C6 C1 C7 120.5(4) . . ? C5 C6 C1 118.6(4) . . ? C5 C6 H17 118(3) . . ? C1 C6 H17 123(3) . . ? F3 C5 C4 117.7(4) . . ? F3 C5 C6 120.3(4) . . ? C4 C5 C6 122.1(4) . . ? F2 C4 C5 120.9(4) . . ? F2 C4 C3 120.2(4) . . ? C5 C4 C3 118.9(4) . . ? F1 C3 C2 120.9(4) . . ? F1 C3 C4 118.2(3) . . ? C2 C3 C4 121.0(4) . . ? C3 C2 C1 119.5(4) . . ? C3 C2 H18 127(2) . . ? C1 C2 H18 114(2) . . ? C9 C8 C13 120.0(4) . . ? C9 C8 C14 119.7(3) . . ? C13 C8 C14 120.2(4) . . ? C12 C13 C8 118.6(4) . . ? C12 C13 H16 117(2) . . ? C8 C13 H16 124(2) . . ? F5 C11 C10 120.4(4) . . ? F5 C11 C12 120.6(4) . . ? C10 C11 C12 118.9(4) . . ? F6 C12 C13 120.5(4) . . ? F6 C12 C11 118.0(4) . . ? C13 C12 C11 121.5(4) . . ? F4 C10 C9 120.9(4) . . ? F4 C10 C11 117.6(4) . . ? C9 C10 C11 121.5(4) . . ? C10 C9 C8 119.4(4) . . ? C10 C9 H15 121(3) . . ? C8 C9 H15 119(3) . . ? O3 C14 O4 124.8(4) . . ? O3 C14 C8 123.1(4) . . ? O4 C14 C8 112.1(3) . . ? C18 C17 C16 117.5(4) . . ? C18 C17 C20 118.3(4) . . ? C16 C17 C20 124.3(4) . . ? C15 C16 C17 119.3(4) . . ? C15 C16 H11 112(3) . . ? C17 C16 H11 128(3) . . ? N1 C15 C16 122.7(4) . . ? N1 C15 H12 115(2) . . ? C16 C15 H12 122(2) . . ? N1 C19 C18 123.1(4) . . ? N1 C19 H14 112(2) . . ? C18 C19 H14 124(2) . . ? C17 C18 C19 120.1(4) . . ? C17 C18 H13 122(3) . . ? C19 C18 H13 117(3) . . ? O5 C20 N2 122.3(4) . . ? O5 C20 C17 118.9(4) . . ? N2 C20 C17 118.8(4) . . ? O6 C26 N4 123.7(4) . . ? O6 C26 C23 119.6(3) . . ? N4 C26 C23 116.7(4) . . ? C22 C23 C24 118.2(4) . . ? C22 C23 C26 124.5(4) . . ? C24 C23 C26 117.3(3) . . ? C21 C22 C23 119.4(4) . . ? C21 C22 H5 122(2) . . ? C23 C22 H5 119(2) . . ? N3 C21 C22 122.5(4) . . ? N3 C21 H6 115(2) . . ? C22 C21 H6 122(2) . . ? N3 C25 C24 123.1(4) . . ? N3 C25 H8 117(2) . . ? C24 C25 H8 119(2) . . ? C25 C24 C23 119.0(4) . . ? C25 C24 H7 120(3) . . ? C23 C24 H7 121(3) . . ? C19 N1 C15 117.3(3) . . ? C20 N2 H9 113(3) . . ? C20 N2 H10 112(4) . . ? H9 N2 H10 134(5) . . ? C25 N3 C21 117.8(4) . . ? C26 N4 H3 114(3) . . ? C26 N4 H4 123(3) . . ? H3 N4 H4 122(4) . . ? C14 O4 H1 109.5 . . ? C7 O2 H2 109.5 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.326 _refine_diff_density_min -0.374 _refine_diff_density_rms 0.085 _database_code_depnum_ccdc_archive 'CCDC 965670' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_datam _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H9 F2 N2 O3' _chemical_formula_weight 279.22 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 Monoclinic _symmetry_space_group_name_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 22.920(4) _cell_length_b 5.2259(8) _cell_length_c 20.566(3) _cell_angle_alpha 90.00 _cell_angle_beta 97.914(12) _cell_angle_gamma 90.00 _cell_volume 2439.9(7) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.520 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1144 _exptl_absorpt_coefficient_mu 0.129 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9808 _exptl_absorpt_correction_T_max 0.9846 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11631 _diffrn_reflns_av_R_equivalents 0.0397 _diffrn_reflns_av_sigmaI/netI 0.0281 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 3.59 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2794 _reflns_number_gt 2184 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0473P)^2^+4.8984P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2794 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0714 _refine_ls_R_factor_gt 0.0533 _refine_ls_wR_factor_ref 0.1291 _refine_ls_wR_factor_gt 0.1197 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _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 0.05215(8) 1.0176(3) 0.10373(9) 0.0198(4) Uani 1 1 d . . . C2 C -0.13523(8) 0.8406(4) 0.19682(9) 0.0239(4) Uani 1 1 d . . . C3 C -0.21990(9) 1.1481(4) 0.17870(10) 0.0291(4) Uani 1 1 d . . . C4 C -0.16889(9) 1.0493(4) 0.15841(9) 0.0258(4) Uani 1 1 d . . . C5 C 0.12206(9) 1.3573(4) 0.12336(10) 0.0263(4) Uani 1 1 d . . . C6 C 0.03505(9) 1.0720(4) 0.16450(9) 0.0253(4) Uani 1 1 d . . . C7 C 0.02681(8) 0.8045(3) 0.05897(9) 0.0205(4) Uani 1 1 d . . . C8 C -0.23168(11) 1.4348(5) 0.08899(11) 0.0410(6) Uani 1 1 d . . . C9 C 0.09670(8) 1.1642(4) 0.08329(9) 0.0241(4) Uani 1 1 d . . . C10 C -0.14947(10) 1.1471(5) 0.10237(11) 0.0366(5) Uani 1 1 d . . . C11 C -0.25176(11) 1.3425(5) 0.14416(11) 0.0355(5) Uani 1 1 d . . . C12 C 0.06274(9) 1.2681(4) 0.20166(9) 0.0271(4) Uani 1 1 d . . . C13 C -0.18171(11) 1.3406(5) 0.06823(12) 0.0472(6) Uani 1 1 d . . . N1 N 0.10566(7) 1.4088(3) 0.18187(8) 0.0236(4) Uani 1 1 d . . . N2 N -0.01756(7) 0.6687(3) 0.07623(8) 0.0240(4) Uani 1 1 d . . . O1 O -0.08882(6) 0.7553(3) 0.18289(7) 0.0312(3) Uani 1 1 d . . . O2 O -0.15967(6) 0.7627(3) 0.24693(7) 0.0328(4) Uani 1 1 d . . . O3 O 0.04914(6) 0.7612(3) 0.00872(6) 0.0263(3) Uani 1 1 d . . . F1 F -0.16524(8) 1.4467(5) 0.01491(9) 0.0705(9) Uani 0.814(4) 1 d P . . F2 F -0.26178(7) 1.6238(3) 0.05422(8) 0.0620(5) Uani 1 1 d . . . F3 F -0.2887(4) 1.4386(18) 0.1524(4) 0.061(3) Uani 0.186(4) 1 d P . . H2 H -0.1361(14) 0.612(7) 0.2769(16) 0.079(10) Uiso 1 1 d . . . H2A H -0.0310(10) 0.534(5) 0.0487(11) 0.033(6) Uiso 1 1 d . . . H2B H -0.0359(10) 0.708(5) 0.1107(11) 0.033(6) Uiso 1 1 d . . . H3 H -0.2324(10) 1.081(5) 0.2164(12) 0.039(6) Uiso 1 1 d . . . H5 H 0.1519(9) 1.464(4) 0.1113(10) 0.028(6) Uiso 1 1 d . . . H6 H 0.0068(10) 0.978(5) 0.1811(12) 0.040(7) Uiso 1 1 d . . . H9 H 0.1085(10) 1.131(5) 0.0421(12) 0.036(6) Uiso 1 1 d . . . H10 H -0.1174(10) 1.082(4) 0.0895(10) 0.026(6) Uiso 1 1 d . . . H12 H 0.0534(9) 1.310(4) 0.2466(11) 0.030(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 0.0185(8) 0.0199(9) 0.0206(9) 0.0010(7) 0.0014(7) 0.0032(7) C2 0.0247(9) 0.0271(10) 0.0209(9) -0.0004(8) 0.0065(7) -0.0022(8) C3 0.0306(10) 0.0325(11) 0.0247(10) 0.0085(9) 0.0061(8) 0.0008(9) C4 0.0290(10) 0.0267(10) 0.0216(9) 0.0030(8) 0.0028(8) -0.0061(8) C5 0.0246(9) 0.0280(10) 0.0273(10) -0.0015(8) 0.0072(8) -0.0053(8) C6 0.0268(10) 0.0270(10) 0.0239(9) -0.0026(8) 0.0096(8) -0.0062(8) C7 0.0227(9) 0.0182(9) 0.0207(8) 0.0002(7) 0.0038(7) 0.0037(7) C8 0.0416(13) 0.0407(13) 0.0386(12) 0.0180(11) -0.0017(10) 0.0031(11) C9 0.0252(9) 0.0275(10) 0.0203(9) -0.0022(8) 0.0056(7) -0.0012(8) C10 0.0324(11) 0.0489(14) 0.0307(11) 0.0101(10) 0.0122(9) 0.0024(11) C11 0.0383(12) 0.0347(12) 0.0328(11) 0.0086(9) 0.0023(9) 0.0029(10) C12 0.0296(10) 0.0301(11) 0.0227(9) -0.0056(8) 0.0077(8) -0.0024(8) C13 0.0510(15) 0.0579(16) 0.0337(12) 0.0258(12) 0.0093(11) -0.0019(13) N1 0.0227(8) 0.0239(8) 0.0241(8) -0.0033(7) 0.0030(6) -0.0019(7) N2 0.0279(8) 0.0221(8) 0.0235(8) -0.0053(7) 0.0083(7) -0.0031(7) O1 0.0280(7) 0.0382(8) 0.0297(7) 0.0004(6) 0.0120(6) 0.0026(6) O2 0.0306(7) 0.0390(9) 0.0320(8) 0.0171(7) 0.0157(6) 0.0116(7) O3 0.0296(7) 0.0263(7) 0.0254(7) -0.0075(6) 0.0115(5) -0.0034(6) F1 0.0592(12) 0.1021(18) 0.0602(12) 0.0614(12) 0.0437(10) 0.0422(12) F2 0.0581(9) 0.0679(11) 0.0603(10) 0.0422(9) 0.0096(8) 0.0183(8) F3 0.048(5) 0.080(6) 0.061(5) 0.030(5) 0.029(4) 0.049(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C9 1.387(3) . ? C1 C6 1.390(2) . ? C1 C7 1.509(3) . ? C2 O1 1.223(2) . ? C2 O2 1.304(2) . ? C2 C4 1.497(3) . ? C3 C11 1.388(3) . ? C3 C4 1.393(3) . ? C3 H3 0.93(2) . ? C4 C10 1.389(3) . ? C5 N1 1.336(2) . ? C5 C9 1.380(3) . ? C5 H5 0.94(2) . ? C6 C12 1.380(3) . ? C6 H6 0.92(2) . ? C7 O3 1.236(2) . ? C7 N2 1.328(2) . ? C8 F2 1.352(3) . ? C8 C13 1.368(4) . ? C8 C11 1.369(3) . ? C9 H9 0.94(2) . ? C10 C13 1.385(3) . ? C10 H10 0.88(2) . ? C11 F3 1.019(7) . ? C12 N1 1.336(2) . ? C12 H12 1.00(2) . ? C13 F1 1.329(3) . ? N2 H2A 0.93(2) . ? N2 H2B 0.90(2) . ? O2 H2 1.09(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 C9 C1 C6 118.03(17) . . ? C9 C1 C7 117.38(16) . . ? C6 C1 C7 124.56(17) . . ? O1 C2 O2 123.61(18) . . ? O1 C2 C4 122.91(17) . . ? O2 C2 C4 113.47(16) . . ? C11 C3 C4 121.46(19) . . ? C11 C3 H3 120.1(15) . . ? C4 C3 H3 118.4(15) . . ? C10 C4 C3 119.36(19) . . ? C10 C4 C2 120.34(18) . . ? C3 C4 C2 120.30(17) . . ? N1 C5 C9 122.50(18) . . ? N1 C5 H5 115.0(13) . . ? C9 C5 H5 122.5(13) . . ? C12 C6 C1 119.01(18) . . ? C12 C6 H6 119.3(15) . . ? C1 C6 H6 121.7(15) . . ? O3 C7 N2 123.11(17) . . ? O3 C7 C1 118.47(16) . . ? N2 C7 C1 118.41(16) . . ? F2 C8 C13 119.1(2) . . ? F2 C8 C11 119.4(2) . . ? C13 C8 C11 121.5(2) . . ? C5 C9 C1 119.35(17) . . ? C5 C9 H9 121.7(15) . . ? C1 C9 H9 119.0(15) . . ? C13 C10 C4 118.7(2) . . ? C13 C10 H10 122.5(14) . . ? C4 C10 H10 118.8(14) . . ? F3 C11 C8 110.3(5) . . ? F3 C11 C3 131.8(5) . . ? C8 C11 C3 117.9(2) . . ? N1 C12 C6 122.82(17) . . ? N1 C12 H12 114.9(13) . . ? C6 C12 H12 122.3(13) . . ? F1 C13 C8 116.9(2) . . ? F1 C13 C10 122.0(2) . . ? C8 C13 C10 121.0(2) . . ? C12 N1 C5 118.28(17) . . ? C7 N2 H2A 116.3(14) . . ? C7 N2 H2B 123.2(15) . . ? H2A N2 H2B 120(2) . . ? C2 O2 H2 115.9(16) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.485 _refine_diff_density_min -0.446 _refine_diff_density_rms 0.054 _database_code_depnum_ccdc_archive 'CCDC 965671' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_shelxl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H12 F2 N2 O4' _chemical_formula_weight 298.25 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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' _cell_length_a 3.7357(5) _cell_length_b 15.625(2) _cell_length_c 10.9260(14) _cell_angle_alpha 90.00 _cell_angle_beta 93.614(7) _cell_angle_gamma 90.00 _cell_volume 636.47(15) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.556 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 308 _exptl_absorpt_coefficient_mu 0.135 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9671 _exptl_absorpt_correction_T_max 0.9840 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6570 _diffrn_reflns_av_R_equivalents 0.0312 _diffrn_reflns_av_sigmaI/netI 0.0223 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.21 _diffrn_reflns_theta_max 27.48 _reflns_number_total 1465 _reflns_number_gt 1368 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0432P)^2^+0.0995P] 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 -0.3(8) _refine_ls_number_reflns 1465 _refine_ls_number_parameters 238 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0334 _refine_ls_R_factor_gt 0.0307 _refine_ls_wR_factor_ref 0.0752 _refine_ls_wR_factor_gt 0.0740 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.082 _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 0.5347(6) 0.09212(15) 0.4089(2) 0.0165(5) Uani 1 1 d . . . C2 C 0.4689(6) 0.08060(16) 0.2834(2) 0.0209(5) Uani 1 1 d . . . C3 C 0.4555(6) 0.17091(15) 0.4603(2) 0.0191(5) Uani 1 1 d . . . C4 C 0.3108(6) 0.23479(15) 0.3847(2) 0.0200(5) Uani 1 1 d . . . C5 C 0.6988(6) 0.02258(15) 0.4901(2) 0.0186(5) Uani 1 1 d . . . C6 C 0.3288(7) 0.14820(16) 0.2142(2) 0.0219(5) Uani 1 1 d . . . N1 N 0.2502(6) 0.22364(12) 0.26334(19) 0.0197(4) Uani 1 1 d . . . N2 N 0.6520(7) -0.05708(14) 0.4498(2) 0.0243(5) Uani 1 1 d . . . O3 O 0.8728(5) 0.04053(12) 0.58633(16) 0.0257(4) Uani 1 1 d . . . C7 C 0.5502(7) 0.50349(17) 0.2370(2) 0.0210(5) Uani 1 1 d . . . C8 C 0.6201(6) 0.65236(16) 0.2993(2) 0.0191(5) Uani 1 1 d . . . C9 C 0.7884(6) 0.62586(15) 0.4105(2) 0.0172(5) Uani 1 1 d . . . C10 C 0.8386(6) 0.53921(16) 0.4364(2) 0.0183(5) Uani 1 1 d . . . C11 C 0.9178(6) 0.69241(15) 0.5027(2) 0.0186(5) Uani 1 1 d . . . C12 C 0.5039(6) 0.59062(16) 0.2173(2) 0.0213(5) Uani 1 1 d . . . C13 C 0.7202(7) 0.48131(16) 0.3478(2) 0.0204(5) Uani 1 1 d . . . O1 O 0.9194(5) 0.76839(11) 0.47507(18) 0.0271(4) Uani 1 1 d . . . O2 O 1.0245(5) 0.66164(12) 0.60911(16) 0.0254(4) Uani 1 1 d . . . F1 F 0.3354(4) 0.61528(10) 0.10919(14) 0.0326(4) Uani 1 1 d . . . F2 F 0.7733(4) 0.39685(9) 0.37078(15) 0.0297(4) Uani 1 1 d . . . O4 O 0.2243(6) 0.85193(13) 0.2611(2) 0.0305(4) Uani 1 1 d . . . H4A H 0.081(10) 0.881(2) 0.219(3) 0.032(9) Uiso 1 1 d . . . H4B H 0.105(12) 0.830(3) 0.312(4) 0.055(13) Uiso 1 1 d . . . H8 H 0.589(8) 0.713(2) 0.283(3) 0.025(7) Uiso 1 1 d . . . H7 H 0.467(8) 0.4654(18) 0.180(3) 0.018(7) Uiso 1 1 d . . . H2 H 1.094(11) 0.709(3) 0.670(4) 0.060(12) Uiso 1 1 d . . . H3 H 0.479(9) 0.182(2) 0.545(3) 0.031(8) Uiso 1 1 d . . . H2B H 0.517(10) -0.071(2) 0.383(3) 0.033(9) Uiso 1 1 d . . . H6 H 0.270(9) 0.1443(19) 0.128(3) 0.029(8) Uiso 1 1 d . . . H2A H 0.537(9) 0.0298(19) 0.247(3) 0.027(8) Uiso 1 1 d . . . H2C H 0.762(9) -0.098(2) 0.489(3) 0.029(8) Uiso 1 1 d . . . H4 H 0.247(9) 0.292(2) 0.418(3) 0.031(8) Uiso 1 1 d . . . H10 H 0.956(9) 0.519(2) 0.505(3) 0.031(8) 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 0.0152(10) 0.0159(11) 0.0183(11) 0.0021(9) 0.0008(9) 0.0001(9) C2 0.0252(13) 0.0197(11) 0.0176(11) -0.0015(10) -0.0001(9) 0.0027(10) C3 0.0240(12) 0.0176(11) 0.0156(11) -0.0020(9) 0.0002(9) -0.0011(9) C4 0.0242(12) 0.0153(10) 0.0204(11) -0.0017(9) 0.0006(9) -0.0003(9) C5 0.0169(11) 0.0201(12) 0.0188(11) 0.0049(9) 0.0014(9) 0.0021(9) C6 0.0264(12) 0.0237(12) 0.0155(12) -0.0001(10) 0.0000(9) 0.0018(10) N1 0.0243(10) 0.0171(9) 0.0174(9) 0.0049(8) -0.0018(8) 0.0000(8) N2 0.0330(11) 0.0155(10) 0.0237(11) 0.0026(9) -0.0040(9) 0.0049(9) O3 0.0287(9) 0.0261(9) 0.0213(9) 0.0034(7) -0.0061(7) -0.0019(8) C7 0.0203(11) 0.0228(12) 0.0198(11) -0.0073(10) -0.0002(9) -0.0031(9) C8 0.0215(11) 0.0175(12) 0.0180(11) 0.0005(9) 0.0002(9) 0.0015(9) C9 0.0169(10) 0.0191(11) 0.0156(11) -0.0015(9) 0.0021(9) 0.0003(9) C10 0.0190(11) 0.0185(11) 0.0170(11) 0.0019(9) -0.0012(9) 0.0000(9) C11 0.0207(11) 0.0166(11) 0.0181(11) -0.0005(9) -0.0011(9) 0.0010(9) C12 0.0222(12) 0.0269(13) 0.0146(11) 0.0017(9) -0.0012(9) 0.0005(10) C13 0.0219(12) 0.0174(12) 0.0222(12) 0.0000(9) 0.0039(9) 0.0012(9) O1 0.0423(10) 0.0148(8) 0.0230(9) 0.0005(7) -0.0073(8) 0.0002(7) O2 0.0397(10) 0.0181(9) 0.0174(9) -0.0009(7) -0.0067(8) -0.0020(8) F1 0.0413(9) 0.0353(9) 0.0193(7) 0.0020(7) -0.0128(6) -0.0003(8) F2 0.0421(9) 0.0135(7) 0.0331(9) -0.0039(6) -0.0022(7) 0.0002(6) O4 0.0362(11) 0.0281(10) 0.0269(10) 0.0046(9) -0.0014(9) 0.0022(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 C1 C2 1.390(3) . ? C1 C3 1.393(3) . ? C1 C5 1.508(3) . ? C2 C6 1.382(4) . ? C2 H2A 0.93(3) . ? C3 C4 1.384(3) . ? C3 H3 0.94(4) . ? C4 N1 1.343(3) . ? C4 H4 0.99(3) . ? C5 O3 1.234(3) . ? C5 N2 1.328(3) . ? C6 N1 1.335(3) . ? C6 H6 0.95(4) . ? N2 H2B 0.88(4) . ? N2 H2C 0.86(3) . ? C7 C13 1.376(4) . ? C7 C12 1.387(4) . ? C7 H7 0.90(3) . ? C8 C12 1.369(3) . ? C8 C9 1.395(3) . ? C8 H8 0.96(3) . ? C9 C10 1.393(3) . ? C9 C11 1.506(3) . ? C10 C13 1.377(3) . ? C10 H10 0.90(4) . ? C11 O1 1.225(3) . ? C11 O2 1.297(3) . ? C12 F1 1.359(3) . ? C13 F2 1.355(3) . ? O2 H2 1.02(4) . ? O4 H4A 0.82(4) . ? O4 H4B 0.81(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 C2 C1 C3 118.9(2) . . ? C2 C1 C5 121.8(2) . . ? C3 C1 C5 119.2(2) . . ? C6 C2 C1 118.5(2) . . ? C6 C2 H2A 122(2) . . ? C1 C2 H2A 120(2) . . ? C4 C3 C1 118.8(2) . . ? C4 C3 H3 118(2) . . ? C1 C3 H3 123(2) . . ? N1 C4 C3 122.1(2) . . ? N1 C4 H4 116.6(19) . . ? C3 C4 H4 121.3(19) . . ? O3 C5 N2 123.1(2) . . ? O3 C5 C1 120.7(2) . . ? N2 C5 C1 116.1(2) . . ? N1 C6 C2 122.7(2) . . ? N1 C6 H6 114.2(18) . . ? C2 C6 H6 123.1(18) . . ? C6 N1 C4 118.9(2) . . ? C5 N2 H2B 124(2) . . ? C5 N2 H2C 119(2) . . ? H2B N2 H2C 117(3) . . ? C13 C7 C12 115.5(2) . . ? C13 C7 H7 124.3(18) . . ? C12 C7 H7 120.2(18) . . ? C12 C8 C9 117.9(2) . . ? C12 C8 H8 122.6(18) . . ? C9 C8 H8 119.5(18) . . ? C10 C9 C8 120.9(2) . . ? C10 C9 C11 120.1(2) . . ? C8 C9 C11 119.0(2) . . ? C13 C10 C9 117.5(2) . . ? C13 C10 H10 118(2) . . ? C9 C10 H10 124(2) . . ? O1 C11 O2 125.0(2) . . ? O1 C11 C9 120.7(2) . . ? O2 C11 C9 114.3(2) . . ? F1 C12 C8 118.7(2) . . ? F1 C12 C7 117.4(2) . . ? C8 C12 C7 124.0(2) . . ? F2 C13 C7 117.5(2) . . ? F2 C13 C10 118.2(2) . . ? C7 C13 C10 124.3(2) . . ? C11 O2 H2 112(2) . . ? H4A O4 H4B 105(4) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.262 _refine_diff_density_min -0.207 _refine_diff_density_rms 0.040 _database_code_depnum_ccdc_archive 'CCDC 965672' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_datam _audit_creation_date 2012-08-01 _audit_creation_method ; Olex2 1.1 (compiled 2011.11.01 svn.r2039, GUI svn.r3906) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C13 H10 F2 N2 O3' _chemical_formula_sum 'C13 H10 F2 N2 O3 ' _chemical_formula_weight 280.23 _chemical_melting_point ? 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' 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 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system Triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 6.570(10) _cell_length_b 7.680(11) _cell_length_c 13.084(18) _cell_angle_alpha 92.357(15) _cell_angle_beta 90.759(9) _cell_angle_gamma 109.87(3) _cell_volume 620.1(15) _cell_formula_units_Z 2 _cell_measurement_reflns_used 1799 _cell_measurement_temperature 150 _cell_measurement_theta_max 27.5 _cell_measurement_theta_min 3.1 _exptl_absorpt_coefficient_mu 0.128 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.818 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_crystal_colour Colorless _exptl_crystal_density_diffrn 1.501 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 288 _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.3 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0688 _diffrn_reflns_av_unetI/netI 0.0620 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 6419 _diffrn_reflns_theta_full 27.53 _diffrn_reflns_theta_max 27.53 _diffrn_reflns_theta_min 1.56 _diffrn_ambient_temperature 150 _diffrn_detector CCD _diffrn_detector_area_resol_mean 13.6612 _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.992 _diffrn_measurement_details ; scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 0.0000 XTD: 49.4653 2theta: 29.5196 scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 120.0000 XTD: 49.4653 2theta: 29.5196 scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 240.0000 XTD: 49.4653 2theta: 29.5196 ; _diffrn_measurement_device ; XtaLABmini: Fixed Chi 2 circle ; _diffrn_measurement_device_type ; Rigaku Mercury375R (2x2 bin mode) ; _diffrn_measurement_method 'profile data from \w-scans' _diffrn_measurement_specimen_support Fiber _diffrn_orient_matrix_type d*Trek _diffrn_orient_matrix_UB_11 -0.036835 _diffrn_orient_matrix_UB_12 0.037173 _diffrn_orient_matrix_UB_13 -0.153227 _diffrn_orient_matrix_UB_21 0.089050 _diffrn_orient_matrix_UB_22 0.094582 _diffrn_orient_matrix_UB_23 -0.048381 _diffrn_orient_matrix_UB_31 0.047880 _diffrn_orient_matrix_UB_32 -0.053343 _diffrn_orient_matrix_UB_33 -0.026794 _diffrn_radiation_monochromator 'Graphite Monochromator' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_source 'Sealed Tube' _diffrn_source_current 12.0 _diffrn_source_power 0.6 _diffrn_source_voltage 50.0 _diffrn_special_details ; ? ; _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 2391 _reflns_number_total 2808 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009) ; _computing_data_collection ; CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. 2008). A64, 112-122 ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _refine_diff_density_max 0.301 _refine_diff_density_min -0.231 _refine_diff_density_rms 0.058 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 221 _refine_ls_number_reflns 2808 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0498 _refine_ls_R_factor_gt 0.0440 _refine_ls_restrained_S_all 1.081 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0718P)^2^+0.0660P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1296 _refine_ls_wR_factor_ref 0.1353 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 H11 H 0.893(3) -0.121(3) 0.7804(14) 0.039(5) Uiso 1 1 d . . . H10 H 0.785(3) 0.226(3) 0.5148(14) 0.042(5) Uiso 1 1 d . . . H6 H 0.504(3) 0.020(2) 0.5996(12) 0.030(4) Uiso 1 1 d . . . H9 H 1.234(3) 0.568(2) 0.2394(14) 0.033(4) Uiso 1 1 d . . . H8 H 0.696(3) 0.554(2) 0.0742(13) 0.038(5) Uiso 1 1 d . . . H2A H 1.088(3) 0.350(3) 0.4365(14) 0.042(5) Uiso 1 1 d . . . H3 H 1.193(3) 0.086(2) 0.7103(14) 0.038(5) Uiso 1 1 d . . . H7 H 1.288(3) 0.906(3) 0.0085(14) 0.038(5) Uiso 1 1 d . . . H2B H 1.331(3) 0.474(3) 0.4464(13) 0.038(5) Uiso 1 1 d . . . H1 H 0.507(4) 0.202(4) 0.2486(19) 0.080(8) Uiso 1 1 d . . . F1 F 0.88194(17) 0.80009(13) -0.04148(7) 0.0438(3) Uani 1 1 d . . . O2 O 0.86891(17) 0.34457(15) 0.31573(8) 0.0345(3) Uani 1 1 d . . . F2 F 1.50282(14) 0.81236(14) 0.14231(8) 0.0443(3) Uani 1 1 d . . . O3 O 1.40614(16) 0.34720(16) 0.60433(8) 0.0370(3) Uani 1 1 d . . . N1 N 0.6757(2) -0.06837(16) 0.69422(9) 0.0275(3) Uani 1 1 d . . . O1 O 0.60602(18) 0.30416(17) 0.19824(8) 0.0390(3) Uani 1 1 d . . . C1 C 1.0305(2) 0.17887(17) 0.60242(9) 0.0224(3) Uani 1 1 d . . . N2 N 1.2101(2) 0.38880(17) 0.47046(9) 0.0281(3) Uani 1 1 d . . . C2 C 1.2307(2) 0.31312(17) 0.55791(10) 0.0244(3) Uani 1 1 d . . . C3 C 1.0586(2) 0.07441(19) 0.68171(10) 0.0257(3) Uani 1 1 d . . . C4 C 0.8020(2) 0.38424(19) 0.23599(10) 0.0258(3) Uani 1 1 d . . . C5 C 0.9411(2) 0.53241(17) 0.17008(10) 0.0239(3) Uani 1 1 d . . . C6 C 0.6486(2) 0.03388(19) 0.61843(10) 0.0275(3) Uani 1 1 d . . . C7 C 1.1964(3) 0.81058(19) 0.04852(11) 0.0329(3) Uani 1 1 d . . . C8 C 0.8441(2) 0.59801(19) 0.09248(10) 0.0264(3) Uani 1 1 d . . . C9 C 1.1645(2) 0.60368(19) 0.18786(11) 0.0263(3) Uani 1 1 d . . . C10 C 0.8204(2) 0.15828(19) 0.56977(10) 0.0260(3) Uani 1 1 d . . . C11 C 0.8775(2) -0.04861(19) 0.72486(10) 0.0275(3) Uani 1 1 d . . . C12 C 1.2855(2) 0.7409(2) 0.12583(11) 0.0300(3) Uani 1 1 d . . . C13 C 0.9751(3) 0.73522(19) 0.03409(10) 0.0302(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.0582(6) 0.0398(5) 0.0346(5) 0.0135(4) -0.0068(4) 0.0170(4) O2 0.0357(6) 0.0389(6) 0.0302(5) 0.0101(4) -0.0043(4) 0.0137(5) F2 0.0244(5) 0.0459(6) 0.0578(6) 0.0036(4) 0.0043(4) 0.0057(4) O3 0.0220(5) 0.0460(7) 0.0396(6) 0.0175(5) -0.0044(4) 0.0054(4) N1 0.0290(6) 0.0268(6) 0.0249(6) 0.0011(4) 0.0027(4) 0.0070(5) O1 0.0289(6) 0.0465(7) 0.0320(6) 0.0134(5) -0.0043(4) -0.0007(5) C1 0.0232(6) 0.0219(6) 0.0223(6) -0.0002(5) 0.0004(5) 0.0082(5) N2 0.0227(6) 0.0324(6) 0.0265(6) 0.0078(5) -0.0011(5) 0.0051(5) C2 0.0224(6) 0.0252(7) 0.0267(6) 0.0034(5) 0.0000(5) 0.0091(5) C3 0.0251(7) 0.0303(7) 0.0238(7) 0.0017(5) -0.0009(5) 0.0121(5) C4 0.0275(7) 0.0272(7) 0.0243(6) 0.0010(5) -0.0012(5) 0.0115(5) C5 0.0284(7) 0.0227(6) 0.0217(6) -0.0012(5) -0.0001(5) 0.0106(5) C6 0.0237(6) 0.0305(7) 0.0270(7) 0.0013(5) -0.0009(5) 0.0076(5) C7 0.0414(8) 0.0250(7) 0.0308(7) 0.0025(5) 0.0078(6) 0.0091(6) C8 0.0299(7) 0.0265(7) 0.0238(6) -0.0011(5) -0.0029(5) 0.0114(5) C9 0.0278(7) 0.0270(7) 0.0261(7) -0.0011(5) -0.0010(5) 0.0121(5) C10 0.0250(6) 0.0287(7) 0.0251(6) 0.0033(5) -0.0011(5) 0.0099(5) C11 0.0329(7) 0.0280(7) 0.0234(6) 0.0050(5) 0.0023(5) 0.0120(5) C12 0.0252(7) 0.0286(7) 0.0349(7) -0.0036(5) 0.0036(6) 0.0078(5) C13 0.0430(8) 0.0259(7) 0.0235(7) 0.0011(5) -0.0032(6) 0.0144(6) _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 C13 1.353(2) . ? O2 C4 1.216(2) . ? F2 C12 1.355(3) . ? O3 C2 1.237(2) . ? N1 C6 1.337(2) . ? N1 C11 1.336(3) . ? O1 H1 1.08(3) . ? O1 C4 1.304(2) . ? C1 C2 1.510(2) . ? C1 C3 1.385(2) . ? C1 C10 1.395(3) . ? N2 H2A 0.87(2) . ? N2 H2B 0.91(2) . ? N2 C2 1.330(2) . ? C3 H3 0.929(19) . ? C3 C11 1.387(2) . ? C4 C5 1.506(2) . ? C5 C8 1.391(2) . ? C5 C9 1.393(3) . ? C6 H6 0.945(18) . ? C6 C10 1.389(2) . ? C7 H7 0.96(2) . ? C7 C12 1.376(3) . ? C7 C13 1.377(3) . ? C8 H8 0.942(19) . ? C8 C13 1.379(2) . ? C9 H9 0.911(19) . ? C9 C12 1.385(2) . ? C10 H10 0.97(2) . ? C11 H11 0.957(19) . ? 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 C6 118.35(12) . . ? C4 O1 H1 111.6(13) . . ? C3 C1 C2 117.79(14) . . ? C3 C1 C10 118.62(13) . . ? C10 C1 C2 123.57(15) . . ? H2A N2 H2B 122.6(17) . . ? C2 N2 H2A 119.7(13) . . ? C2 N2 H2B 117.4(12) . . ? O3 C2 C1 118.46(15) . . ? O3 C2 N2 123.09(13) . . ? N2 C2 C1 118.45(13) . . ? C1 C3 H3 123.4(12) . . ? C1 C3 C11 119.06(15) . . ? C11 C3 H3 117.5(11) . . ? O2 C4 O1 124.34(14) . . ? O2 C4 C5 122.60(14) . . ? O1 C4 C5 113.06(14) . . ? C8 C5 C4 119.35(15) . . ? C8 C5 C9 120.67(14) . . ? C9 C5 C4 119.97(13) . . ? N1 C6 H6 116.6(11) . . ? N1 C6 C10 122.96(15) . . ? C10 C6 H6 120.4(11) . . ? C12 C7 H7 119.9(12) . . ? C12 C7 C13 116.35(14) . . ? C13 C7 H7 123.8(12) . . ? C5 C8 H8 125.7(11) . . ? C13 C8 H8 116.1(11) . . ? C13 C8 C5 118.14(16) . . ? C5 C9 H9 123.7(12) . . ? C12 C9 H9 118.4(12) . . ? C12 C9 C5 117.89(14) . . ? C1 C10 H10 124.3(11) . . ? C6 C10 H10 117.3(11) . . ? C6 C10 C1 118.40(15) . . ? N1 C11 H11 117.0(12) . . ? N1 C11 C3 122.60(15) . . ? C3 C11 H11 120.3(12) . . ? F2 C12 C7 117.89(14) . . ? F2 C12 C9 118.69(15) . . ? C7 C12 C9 123.42(16) . . ? F1 C13 C7 117.95(14) . . ? F1 C13 C8 118.52(16) . . ? C7 C13 C8 123.52(14) . . ? _database_code_depnum_ccdc_archive 'CCDC 965673'