data_publication_text _audit_update_record ; 2013-10-02 # Formatted by publCIF ; _publ_requested_journal 'Organic Letters' _publ_contact_author_name "Zolt\'an Nov\'ak" _publ_contact_author_address ; 'MTA-ELTE ?Lend\"ulet? Catalysis and Organic Synthesis Research Group, Institute of Chemistry, E\"otv\"os University, P\'azm\'any P\'eter stny. 1/a H-1117 Budapest, Hungary ' ; _publ_contact_author_email novakz@elte.hu _publ_contact_author_phone '+36-1-372-2500#1610' loop_ _publ_author_name ; 'Sinai, \'Ad\'am', 'M\'esz\'aros, \'Ad\'am', 'G\'ati, Tam\'as' 'Kudar, Veronika', 'Pall\'o, Anna', 'Nov\'ak, Zolt\'an' ; _publ_author_address ;'Sinai, \'Ad\'am' 'MTA-ELTE ?Lend\"ulet? Catalysis and Organic Synthesis Research Group, Institute of Chemistry, E\"otv\"os University, P\'azm\'any P\'eter stny. 1/a H-1117 Budapest, Hungary ' 'M\'esz\'aros, \'Ad\'am' 'MTA-ELTE ?Lend\"ulet? Catalysis and Organic Synthesis Research Group, Institute of Chemistry, E\"otv\"os University, P\'azm\'any P\'eter stny. 1/a H-1117 Budapest, Hungary ' 'G\'ati, Tam\'as' 'Servier Research Institute of Medicinal Chemistry, Z\'ahony utca 7. H-1031 Budapest, Hungary' 'Kudar, Veronika' 'Research Centre for Natural Sciences, Hungarian Academy of Sciences, Pusztaszeri \'ut 59-67. H-1025 Budapest, Hungary' 'Pall\'o, Anna' 'Research Centre for Natural Sciences, Hungarian Academy of Sciences, Pusztaszeri \'ut 59-67. H-1025 Budapest, Hungary' 'Nov\'ak, Zolt\'an' 'MTA-ELTE ?Lend\"ulet? Catalysis and Organic Synthesis Research Group, Institute of Chemistry, E\"otv\"os University, P\'azm\'any P\'eter stny. 1/a H-1117 Budapest, Hungary ' ; data_3gg _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-(bis(4-fluorophenyl)methylene)-2-tert-butyl -2,4-dihydro-1H-benzo[d][1,3]oxazine ; _chemical_name_common ? _chemical_melting_point 397(2) _chemical_formula_moiety 'C25 H21 F2 N O' _chemical_formula_sum 'C25 H21 F2 N O' _chemical_formula_weight 389.43 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'F' 'F' 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.0188(2) _cell_length_b 9.7294(3) _cell_length_c 17.4629(6) _cell_angle_alpha 75.170(2) _cell_angle_beta 88.700(2) _cell_angle_gamma 85.311(2) _cell_volume 985.24(6) _cell_formula_units_Z 2 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 2991 _cell_measurement_theta_min 7.39 _cell_measurement_theta_max 68.06 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.313 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.758 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_max 0.949 _exptl_absorpt_correction_T_min 0.828 _exptl_absorpt_process_details ; T.Higashi, Numerical Absorption Correction, NUMABS, 2002 ; _exptl_special_details ? _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 1.54187 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type RAXIS-RAPID _diffrn_measurement_method dtprofit.ref _diffrn_detector_area_resol_mean 10.0000 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6765 _diffrn_reflns_av_R_equivalents 0.0549 _diffrn_reflns_av_sigmaI/netI 0.0857 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 7.38 _diffrn_reflns_theta_max 51.14 _reflns_number_total 1936 _reflns_number_gt 1070 _reflns_threshold_expression >2sigma(I) _diffrn_special_details ; NUMSTD=0,FUDGE=0.01,TEMP=-180.0,DIRECT=0.0,SCANUM=1,XDIST=127.4,MITH=N ABSCOR=Y,DECAY=N,REDUN=Y,DECPAR=0.0,AVERAGE=N,ABSTYPE=NUM2,MODIFY=N ABSAV=0.9156,ABSMIN=0.8277,ABSMAX=0.9487,ABSLS=1.0, FACES=0,GRIDA=6,GRIDB=6,GRIDC=6,TYPE=0 Frame N=1,PHI=0.0,CHI=45.0,OMEGA=6.0,206.0,5.0,COUPLE=0.00 Frame N=2,PHI=0.0,CHI=15.0,OMEGA=5.0,180.0,5.0,COUPLE=0.00 Frame N=3,PHI=90.0,CHI=45.0,OMEGA=32.0,182.0,5.0,COUPLE=0.00 Frame N=4,PHI=180.0,CHI=45.0,OMEGA=30.0,190.0,5.0,COUPLE=0.00 Frame N=5,PHI=180.0,CHI=30.0,OMEGA=70.0,75.0,5.0,COUPLE=0.00 U-matrix U11=0.092589,U12=-0.018859,U13=-0.045036,U21=-0.086540, 083554,U23=0.000182,U31=-0.108296,U32=0.063543,U33=-0.038482 ; _computing_data_collection ; 'CrystalClear (Rigaku/MSC Inc., 2006)' ; _computing_cell_refinement ; 'CrystalClear (Rigaku/MSC Inc., 2006)' ; _computing_data_reduction ; 'CrystalClear (Rigaku/MSC Inc., 2006)' ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; 'ORTEP-3 for Windows (Farrugia, 1997)' ; _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1225P)^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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0023(15) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1936 _refine_ls_number_parameters 266 _refine_ls_number_restraints 30 _refine_ls_R_factor_all 0.1251 _refine_ls_R_factor_gt 0.0741 _refine_ls_wR_factor_ref 0.2521 _refine_ls_wR_factor_gt 0.1748 _refine_ls_goodness_of_fit_ref 1.228 _refine_ls_restrained_S_all 1.238 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _iucr_refine_reflections_details 3aa.hkl 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 F28 F -0.6618(6) 0.8054(4) 0.0314(2) 0.0578(13) Uani 1 1 d . . . F29 F 0.1259(6) 1.0078(4) 0.4186(2) 0.0622(13) Uani 1 1 d . . . O3 O 0.0312(7) 0.3668(4) 0.2289(2) 0.0479(14) Uani 1 1 d . . . N1 N 0.3614(10) 0.2173(5) 0.2496(3) 0.0426(16) Uani 1 1 d . . . C2 C 0.1845(13) 0.2659(7) 0.2105(4) 0.0381(18) Uani 1 1 d . . . C4 C 0.0945(11) 0.4492(7) 0.2803(4) 0.0374(19) Uani 1 1 d . . . C5 C 0.2695(11) 0.3769(7) 0.3361(4) 0.0401(18) Uani 1 1 d . . . C6 C 0.3188(12) 0.4117(7) 0.4066(4) 0.046(2) Uani 1 1 d . . . H6 H 0.2233 0.4809 0.4237 0.055 Uiso 1 1 calc R . . C7 C 0.5010(13) 0.3487(7) 0.4518(4) 0.054(2) Uani 1 1 d . . . H7 H 0.5299 0.3741 0.4994 0.065 Uiso 1 1 calc R . . C8 C 0.6439(11) 0.2471(7) 0.4277(4) 0.050(2) Uani 1 1 d . . . H8 H 0.7764 0.2082 0.4563 0.061 Uiso 1 1 calc R . . C9 C 0.5898(12) 0.2050(7) 0.3624(4) 0.053(2) Uani 1 1 d . . . H9 H 0.6791 0.1300 0.3484 0.064 Uiso 1 1 calc R . . C10 C 0.4107(13) 0.2678(7) 0.3165(4) 0.0429(19) Uani 1 1 d . . . C11 C -0.0161(11) 0.5790(7) 0.2665(4) 0.0420(19) Uani 1 1 d . . . C12 C -0.1870(12) 0.6326(7) 0.2043(4) 0.0433(19) Uani 1 1 d U . . C13 C -0.3537(11) 0.5538(7) 0.1876(4) 0.044(2) Uani 1 1 d . . . H13 H -0.3574 0.4571 0.2168 0.052 Uiso 1 1 calc R . . C14 C -0.5144(12) 0.6103(8) 0.1304(4) 0.048(2) Uani 1 1 d . . . H14 H -0.6287 0.5548 0.1211 0.058 Uiso 1 1 calc R . . C15 C -0.5035(12) 0.7495(8) 0.0875(4) 0.0455(19) Uani 1 1 d U . . C16 C -0.3430(12) 0.8307(7) 0.0994(4) 0.047(2) Uani 1 1 d U . . H16 H -0.3381 0.9256 0.0677 0.056 Uiso 1 1 calc R . . C17 C -0.1873(12) 0.7758(7) 0.1572(4) 0.0477(19) Uani 1 1 d U . . H17 H -0.0770 0.8344 0.1663 0.057 Uiso 1 1 calc R . . C18 C 0.0350(11) 0.6833(6) 0.3129(4) 0.0405(18) Uani 1 1 d . . . C19 C -0.1290(11) 0.7236(7) 0.3628(4) 0.050(2) Uani 1 1 d . . . H19 H -0.2637 0.6773 0.3721 0.060 Uiso 1 1 calc R . . C20 C -0.0927(12) 0.8332(6) 0.3991(4) 0.047(2) Uani 1 1 d . . . H20 H -0.2015 0.8600 0.4339 0.056 Uiso 1 1 calc R . . C21 C 0.0975(13) 0.9003(7) 0.3841(4) 0.047(2) Uani 1 1 d . . . C22 C 0.2626(12) 0.8622(7) 0.3368(4) 0.052(2) Uani 1 1 d . . . H22 H 0.3966 0.9093 0.3284 0.063 Uiso 1 1 calc R . . C23 C 0.2298(11) 0.7529(6) 0.3011(4) 0.0415(18) Uani 1 1 d U . . H23 H 0.3432 0.7254 0.2680 0.050 Uiso 1 1 calc R . . C24 C 0.0981(11) 0.2136(7) 0.1435(4) 0.0435(19) Uani 1 1 d . . . C25 C 0.0710(11) 0.3421(7) 0.0695(4) 0.059(2) Uani 1 1 d . . . H25A H 0.0090 0.3112 0.0258 0.088 Uiso 1 1 calc R . . H25B H 0.2168 0.3785 0.0540 0.088 Uiso 1 1 calc R . . H25C H -0.0300 0.4176 0.0821 0.088 Uiso 1 1 calc R . . C26 C -0.1237(10) 0.1511(7) 0.1650(4) 0.052(2) Uani 1 1 d . . . H26A H -0.1759 0.1169 0.1209 0.078 Uiso 1 1 calc R . . H26B H -0.2327 0.2245 0.1755 0.078 Uiso 1 1 calc R . . H26C H -0.1061 0.0713 0.2124 0.078 Uiso 1 1 calc R . . C27 C 0.2704(11) 0.1027(7) 0.1239(4) 0.054(2) Uani 1 1 d . . . H27A H 0.2151 0.0682 0.0804 0.081 Uiso 1 1 calc R . . H27B H 0.2953 0.0224 0.1708 0.081 Uiso 1 1 calc R . . H27C H 0.4109 0.1463 0.1081 0.081 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F28 0.063(3) 0.057(3) 0.057(3) -0.024(2) -0.012(2) 0.004(2) F29 0.085(3) 0.047(2) 0.064(3) -0.033(2) -0.006(2) 0.003(2) O3 0.051(3) 0.045(3) 0.052(3) -0.025(3) -0.005(3) 0.011(2) N1 0.039(4) 0.041(4) 0.049(4) -0.019(3) -0.006(3) 0.009(3) C2 0.044(5) 0.036(4) 0.036(5) -0.015(4) 0.005(4) 0.004(4) C4 0.047(5) 0.028(4) 0.045(5) -0.024(4) 0.004(4) -0.004(4) C5 0.032(4) 0.039(4) 0.051(5) -0.018(4) -0.011(4) 0.010(4) C6 0.045(5) 0.048(5) 0.052(5) -0.028(4) 0.004(4) -0.006(4) C7 0.070(6) 0.049(5) 0.049(5) -0.021(4) -0.009(5) 0.000(5) C8 0.057(5) 0.051(5) 0.046(5) -0.023(4) -0.019(4) 0.017(4) C9 0.057(6) 0.055(5) 0.051(5) -0.027(4) -0.013(5) 0.016(4) C10 0.052(5) 0.046(5) 0.036(5) -0.022(4) -0.006(4) -0.001(4) C11 0.051(5) 0.029(4) 0.051(5) -0.021(4) -0.008(4) 0.003(4) C12 0.045(4) 0.043(4) 0.046(4) -0.023(3) 0.002(3) 0.009(3) C13 0.045(5) 0.033(4) 0.055(5) -0.017(4) -0.003(4) 0.000(4) C14 0.043(5) 0.050(5) 0.059(5) -0.032(4) -0.006(4) 0.015(4) C15 0.046(4) 0.048(4) 0.046(4) -0.020(3) -0.012(3) 0.008(3) C16 0.054(4) 0.043(4) 0.047(4) -0.020(3) -0.002(3) 0.002(3) C17 0.052(4) 0.045(4) 0.054(4) -0.028(3) -0.004(3) 0.002(3) C18 0.036(4) 0.039(4) 0.048(5) -0.015(4) -0.004(4) 0.002(4) C19 0.044(5) 0.043(4) 0.064(5) -0.018(4) 0.010(4) -0.005(4) C20 0.058(5) 0.032(4) 0.053(5) -0.018(4) 0.007(4) 0.006(4) C21 0.053(5) 0.034(4) 0.060(5) -0.025(4) -0.003(4) 0.003(4) C22 0.061(5) 0.042(4) 0.056(5) -0.018(4) 0.004(4) 0.002(4) C23 0.044(4) 0.032(3) 0.049(4) -0.016(3) 0.002(3) 0.012(3) C24 0.035(5) 0.055(5) 0.051(5) -0.035(4) -0.013(4) 0.012(4) C25 0.077(6) 0.055(5) 0.046(5) -0.024(4) -0.010(4) 0.017(4) C26 0.036(4) 0.064(5) 0.067(5) -0.040(4) 0.002(4) -0.003(4) C27 0.063(5) 0.054(5) 0.054(5) -0.030(4) -0.001(4) 0.001(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 F28 C15 1.359(7) . ? F29 C21 1.358(7) . ? O3 C2 1.386(7) . ? O3 C4 1.424(6) . ? N1 C2 1.268(7) . ? N1 C10 1.424(8) . ? C2 C24 1.508(8) . ? C4 C11 1.345(8) . ? C4 C5 1.459(8) . ? C5 C10 1.411(8) . ? C5 C6 1.402(8) . ? C6 C7 1.371(8) . ? C6 H6 0.9500 . ? C7 C8 1.397(8) . ? C7 H7 0.9500 . ? C8 C9 1.361(8) . ? C8 H8 0.9500 . ? C9 C10 1.363(8) . ? C9 H9 0.9500 . ? C11 C12 1.478(8) . ? C11 C18 1.505(8) . ? C12 C13 1.390(8) . ? C12 C17 1.425(8) . ? C13 C14 1.383(7) . ? C13 H13 0.9500 . ? C14 C15 1.376(8) . ? C14 H14 0.9500 . ? C15 C16 1.349(8) . ? C16 C17 1.367(8) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 C23 1.387(8) . ? C18 C19 1.400(8) . ? C19 C20 1.405(8) . ? C19 H19 0.9500 . ? C20 C21 1.352(8) . ? C20 H20 0.9500 . ? C21 C22 1.367(9) . ? C22 C23 1.391(8) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? C24 C26 1.512(8) . ? C24 C27 1.532(7) . ? C24 C25 1.551(8) . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? 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 O3 C4 119.5(5) . . ? C2 N1 C10 119.6(6) . . ? N1 C2 O3 123.9(6) . . ? N1 C2 C24 125.9(6) . . ? O3 C2 C24 110.0(6) . . ? C11 C4 O3 113.5(6) . . ? C11 C4 C5 133.0(6) . . ? O3 C4 C5 113.5(5) . . ? C10 C5 C6 116.2(7) . . ? C10 C5 C4 118.3(6) . . ? C6 C5 C4 125.4(6) . . ? C7 C6 C5 121.8(6) . . ? C7 C6 H6 119.1 . . ? C5 C6 H6 119.1 . . ? C6 C7 C8 120.0(7) . . ? C6 C7 H7 120.0 . . ? C8 C7 H7 120.0 . . ? C9 C8 C7 118.8(7) . . ? C9 C8 H8 120.6 . . ? C7 C8 H8 120.6 . . ? C10 C9 C8 121.6(7) . . ? C10 C9 H9 119.2 . . ? C8 C9 H9 119.2 . . ? C9 C10 C5 121.3(7) . . ? C9 C10 N1 118.8(6) . . ? C5 C10 N1 119.9(7) . . ? C4 C11 C12 123.9(6) . . ? C4 C11 C18 121.0(6) . . ? C12 C11 C18 115.0(6) . . ? C13 C12 C17 115.9(7) . . ? C13 C12 C11 124.9(6) . . ? C17 C12 C11 119.2(6) . . ? C14 C13 C12 122.8(7) . . ? C14 C13 H13 118.6 . . ? C12 C13 H13 118.6 . . ? C15 C14 C13 117.9(7) . . ? C15 C14 H14 121.1 . . ? C13 C14 H14 121.1 . . ? C16 C15 F28 119.7(7) . . ? C16 C15 C14 122.3(8) . . ? F28 C15 C14 118.0(7) . . ? C15 C16 C17 119.8(7) . . ? C15 C16 H16 120.1 . . ? C17 C16 H16 120.1 . . ? C16 C17 C12 121.3(7) . . ? C16 C17 H17 119.3 . . ? C12 C17 H17 119.3 . . ? C23 C18 C19 118.6(6) . . ? C23 C18 C11 121.9(6) . . ? C19 C18 C11 119.1(6) . . ? C18 C19 C20 119.4(6) . . ? C18 C19 H19 120.3 . . ? C20 C19 H19 120.3 . . ? C21 C20 C19 119.8(6) . . ? C21 C20 H20 120.1 . . ? C19 C20 H20 120.1 . . ? C20 C21 F29 118.5(6) . . ? C20 C21 C22 122.4(6) . . ? F29 C21 C22 119.2(7) . . ? C21 C22 C23 118.4(7) . . ? C21 C22 H22 120.8 . . ? C23 C22 H22 120.8 . . ? C18 C23 C22 121.4(6) . . ? C18 C23 H23 119.3 . . ? C22 C23 H23 119.3 . . ? C26 C24 C2 110.8(5) . . ? C26 C24 C27 110.7(5) . . ? C2 C24 C27 109.1(6) . . ? C26 C24 C25 109.9(6) . . ? C2 C24 C25 108.1(5) . . ? C27 C24 C25 108.1(5) . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C24 C26 H26A 109.5 . . ? C24 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C24 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C24 C27 H27A 109.5 . . ? C24 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C24 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C10 N1 C2 O3 -0.3(9) . . . . ? C10 N1 C2 C24 -173.8(6) . . . . ? C4 O3 C2 N1 16.9(9) . . . . ? C4 O3 C2 C24 -168.7(5) . . . . ? C2 O3 C4 C11 151.4(5) . . . . ? C2 O3 C4 C5 -27.3(7) . . . . ? C11 C4 C5 C10 -155.1(7) . . . . ? O3 C4 C5 C10 23.2(8) . . . . ? C11 C4 C5 C6 21.2(11) . . . . ? O3 C4 C5 C6 -160.5(6) . . . . ? C10 C5 C6 C7 3.4(9) . . . . ? C4 C5 C6 C7 -173.0(6) . . . . ? C5 C6 C7 C8 0.2(10) . . . . ? C6 C7 C8 C9 -4.8(10) . . . . ? C7 C8 C9 C10 5.6(10) . . . . ? C8 C9 C10 C5 -1.8(10) . . . . ? C8 C9 C10 N1 -179.1(6) . . . . ? C6 C5 C10 C9 -2.7(9) . . . . ? C4 C5 C10 C9 173.9(6) . . . . ? C6 C5 C10 N1 174.6(5) . . . . ? C4 C5 C10 N1 -8.7(9) . . . . ? C2 N1 C10 C9 173.8(6) . . . . ? C2 N1 C10 C5 -3.5(9) . . . . ? O3 C4 C11 C12 0.0(8) . . . . ? C5 C4 C11 C12 178.4(6) . . . . ? O3 C4 C11 C18 -177.6(5) . . . . ? C5 C4 C11 C18 0.8(10) . . . . ? C4 C11 C12 C13 43.3(9) . . . . ? C18 C11 C12 C13 -139.0(6) . . . . ? C4 C11 C12 C17 -137.4(6) . . . . ? C18 C11 C12 C17 40.3(7) . . . . ? C17 C12 C13 C14 -1.5(9) . . . . ? C11 C12 C13 C14 177.9(5) . . . . ? C12 C13 C14 C15 1.5(9) . . . . ? C13 C14 C15 C16 0.1(9) . . . . ? C13 C14 C15 F28 -179.8(5) . . . . ? F28 C15 C16 C17 178.2(5) . . . . ? C14 C15 C16 C17 -1.7(10) . . . . ? C15 C16 C17 C12 1.7(9) . . . . ? C13 C12 C17 C16 -0.1(8) . . . . ? C11 C12 C17 C16 -179.5(5) . . . . ? C4 C11 C18 C23 72.4(8) . . . . ? C12 C11 C18 C23 -105.4(7) . . . . ? C4 C11 C18 C19 -115.0(7) . . . . ? C12 C11 C18 C19 67.2(8) . . . . ? C23 C18 C19 C20 0.3(10) . . . . ? C11 C18 C19 C20 -172.5(6) . . . . ? C18 C19 C20 C21 1.4(10) . . . . ? C19 C20 C21 F29 178.6(5) . . . . ? C19 C20 C21 C22 -2.4(11) . . . . ? C20 C21 C22 C23 1.8(11) . . . . ? F29 C21 C22 C23 -179.2(5) . . . . ? C19 C18 C23 C22 -0.9(10) . . . . ? C11 C18 C23 C22 171.6(6) . . . . ? C21 C22 C23 C18 0.0(10) . . . . ? N1 C2 C24 C26 116.2(7) . . . . ? O3 C2 C24 C26 -58.0(7) . . . . ? N1 C2 C24 C27 -6.0(9) . . . . ? O3 C2 C24 C27 179.8(5) . . . . ? N1 C2 C24 C25 -123.3(7) . . . . ? O3 C2 C24 C25 62.4(6) . . . . ? _diffrn_measured_fraction_theta_max 0.918 _diffrn_reflns_theta_full 51.14 _diffrn_measured_fraction_theta_full 0.918 _refine_diff_density_max 0.322 _refine_diff_density_min -0.364 _refine_diff_density_rms 0.081