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_3j _audit_creation_method SHELXL-97 _chemical_name_systematic ; (Z)-2-tert-butyl-4-((4-nitrophenyl)(phenyl)methylene) -4H-benzo[d][1,3]oxazine ; _chemical_name_common ? _chemical_melting_point 416(2) _chemical_formula_moiety 'C25 H22 N2 O3' _chemical_formula_sum 'C25 H22 N2 O3' _chemical_formula_weight 398.45 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 5.98980(10) _cell_length_b 19.4167(5) _cell_length_c 18.1253(4) _cell_angle_alpha 90.00 _cell_angle_beta 98.2730(10) _cell_angle_gamma 90.00 _cell_volume 2086.07(8) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 5870 _cell_measurement_theta_min 6.72 _cell_measurement_theta_max 69.91 _exptl_crystal_description Prism _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.269 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 0.675 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_max 0.949 _exptl_absorpt_correction_T_min 0.844 _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 9647 _diffrn_reflns_av_R_equivalents 0.0775 _diffrn_reflns_av_sigmaI/netI 0.1037 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 6.72 _diffrn_reflns_theta_max 55.08 _reflns_number_total 2451 _reflns_number_gt 1507 _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=0.9283,ABSMIN=0.8438,ABSMAX=0.9495,ABSLS=1.0, FACES=0,GRIDA=6,GRIDB=6,GRIDC=6,TYPE=0 Frame N=1,PHI=0.0,CHI=15.0,OMEGA=40.0,210.0,5.0,COUPLE=0.00 Frame N=2,PHI=0.0,CHI=45.0,OMEGA=5.0,130.0,5.0,COUPLE=0.00 Frame N=3,PHI=90.0,CHI=45.0,OMEGA=25.0,185.0,5.0,COUPLE=0.00 U-matrix U11=-0.044431,U12=0.004160,U13=-0.055395,U21=-0.162743, 007410,U23=0.003714,U31=-0.020101,U32=0.050796,U33=0.005078 ; _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^)+(0.0634P)^2^+0.0723P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2451 _refine_ls_number_parameters 274 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1272 _refine_ls_R_factor_gt 0.0713 _refine_ls_wR_factor_ref 0.1590 _refine_ls_wR_factor_gt 0.1392 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _iucr_refine_reflections_details 3j.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 O1 O -0.6484(5) 0.18895(17) 0.13180(17) 0.0702(11) Uani 1 1 d . . . O2 O -0.7016(5) 0.14164(17) 0.23569(17) 0.0644(11) Uani 1 1 d . . . O3 O 0.2570(4) 0.24215(17) 0.43895(14) 0.0471(9) Uani 1 1 d . . . N1 N 0.6131(6) 0.2296(2) 0.50886(17) 0.0419(10) Uani 1 1 d . . . N2 N -0.5965(6) 0.1796(2) 0.1987(2) 0.0543(12) Uani 1 1 d . . . C2 C 0.4212(8) 0.2053(3) 0.4827(2) 0.0431(13) Uani 1 1 d . . . C4 C 0.3035(7) 0.3072(3) 0.4101(2) 0.0431(13) Uani 1 1 d . . . C5 C 0.4970(7) 0.3416(3) 0.4522(2) 0.0391(12) Uani 1 1 d . . . C6 C 0.5428(7) 0.4124(3) 0.4504(2) 0.0486(13) Uani 1 1 d . . . H6 H 0.4385 0.4419 0.4213 0.058 Uiso 1 1 calc R . . C7 C 0.7359(7) 0.4402(2) 0.4901(2) 0.0503(13) Uani 1 1 d . . . H7 H 0.7624 0.4883 0.4879 0.060 Uiso 1 1 calc R . . C8 C 0.8912(7) 0.3985(3) 0.5331(2) 0.0530(14) Uani 1 1 d . . . H8 H 1.0252 0.4177 0.5595 0.064 Uiso 1 1 calc R . . C9 C 0.8499(7) 0.3294(3) 0.5371(2) 0.0475(13) Uani 1 1 d . . . H9 H 0.9567 0.3007 0.5663 0.057 Uiso 1 1 calc R . . C10 C 0.6531(7) 0.3003(3) 0.4989(2) 0.0441(13) Uani 1 1 d . . . C11 C 0.1654(7) 0.3272(2) 0.3476(2) 0.0396(12) Uani 1 1 d . . . C12 C -0.0280(7) 0.2861(2) 0.3113(2) 0.0396(12) Uani 1 1 d . . . C13 C -0.1576(7) 0.2435(2) 0.3497(2) 0.0456(13) Uani 1 1 d . . . H13 H -0.1179 0.2381 0.4020 0.055 Uiso 1 1 calc R . . C14 C -0.3435(7) 0.2087(2) 0.3133(2) 0.0437(12) Uani 1 1 d . . . H14 H -0.4317 0.1802 0.3404 0.052 Uiso 1 1 calc R . . C15 C -0.3987(7) 0.2162(2) 0.2373(2) 0.0430(12) Uani 1 1 d . . . C16 C -0.2756(7) 0.2574(2) 0.1974(2) 0.0478(13) Uani 1 1 d . . . H16 H -0.3162 0.2621 0.1450 0.057 Uiso 1 1 calc R . . C17 C -0.0908(6) 0.2924(2) 0.2341(2) 0.0413(12) Uani 1 1 d . . . H17 H -0.0049 0.3212 0.2065 0.050 Uiso 1 1 calc R . . C18 C 0.2099(7) 0.3924(3) 0.3099(2) 0.0408(12) Uani 1 1 d . . . C19 C 0.0572(7) 0.4472(3) 0.3071(2) 0.0532(14) Uani 1 1 d . . . H19 H -0.0746 0.4428 0.3303 0.064 Uiso 1 1 calc R . . C20 C 0.0965(8) 0.5075(3) 0.2710(3) 0.0619(15) Uani 1 1 d . . . H20 H -0.0069 0.5446 0.2708 0.074 Uiso 1 1 calc R . . C21 C 0.2839(9) 0.5150(3) 0.2350(2) 0.0595(15) Uani 1 1 d . . . H21 H 0.3076 0.5563 0.2091 0.071 Uiso 1 1 calc R . . C22 C 0.4362(7) 0.4610(3) 0.2374(2) 0.0516(14) Uani 1 1 d . . . H22 H 0.5673 0.4658 0.2139 0.062 Uiso 1 1 calc R . . C23 C 0.3992(7) 0.4001(2) 0.2738(2) 0.0457(13) Uani 1 1 d . . . H23 H 0.5038 0.3633 0.2742 0.055 Uiso 1 1 calc R . . C24 C 0.3424(7) 0.1345(2) 0.5006(2) 0.0411(12) Uani 1 1 d . . . C25 C 0.2285(7) 0.0977(2) 0.4300(2) 0.0587(14) Uani 1 1 d . . . H25A H 0.3380 0.0917 0.3952 0.088 Uiso 1 1 calc R . . H25B H 0.1013 0.1254 0.4063 0.088 Uiso 1 1 calc R . . H25C H 0.1736 0.0525 0.4434 0.088 Uiso 1 1 calc R . . C26 C 0.1742(7) 0.1431(2) 0.5562(2) 0.0607(14) Uani 1 1 d . . . H26A H 0.0433 0.1694 0.5328 0.091 Uiso 1 1 calc R . . H26B H 0.2470 0.1677 0.6004 0.091 Uiso 1 1 calc R . . H26C H 0.1249 0.0976 0.5709 0.091 Uiso 1 1 calc R . . C27 C 0.5429(7) 0.0920(2) 0.5370(2) 0.0537(14) Uani 1 1 d . . . H27A H 0.4900 0.0469 0.5514 0.080 Uiso 1 1 calc R . . H27B H 0.6172 0.1161 0.5814 0.080 Uiso 1 1 calc R . . H27C H 0.6504 0.0859 0.5015 0.080 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.059(2) 0.103(3) 0.042(2) 0.002(2) -0.0145(17) -0.0108(19) O2 0.052(2) 0.071(3) 0.066(2) 0.010(2) -0.0081(17) -0.0150(19) O3 0.0387(19) 0.055(3) 0.0438(17) 0.0026(17) -0.0080(14) 0.0041(18) N1 0.037(2) 0.045(3) 0.041(2) -0.004(2) -0.0043(17) -0.005(2) N2 0.046(3) 0.064(4) 0.050(3) 0.001(3) -0.005(2) 0.001(2) C2 0.035(3) 0.058(4) 0.034(3) -0.002(3) -0.003(2) 0.002(3) C4 0.040(3) 0.045(4) 0.041(3) 0.001(3) -0.003(2) 0.007(3) C5 0.031(3) 0.044(4) 0.040(3) -0.008(3) -0.002(2) -0.007(3) C6 0.042(3) 0.058(4) 0.042(3) -0.010(3) -0.006(2) -0.001(3) C7 0.049(3) 0.049(4) 0.050(3) -0.007(3) -0.002(2) -0.001(3) C8 0.046(3) 0.059(4) 0.049(3) -0.009(3) -0.010(2) -0.003(3) C9 0.043(3) 0.053(4) 0.042(3) -0.006(3) -0.007(2) -0.001(3) C10 0.036(3) 0.056(4) 0.039(3) -0.007(3) 0.003(2) -0.001(3) C11 0.032(3) 0.050(4) 0.035(3) 0.002(3) -0.001(2) 0.004(3) C12 0.034(3) 0.046(3) 0.037(3) -0.002(2) -0.004(2) 0.004(2) C13 0.039(3) 0.054(4) 0.040(3) 0.001(3) -0.007(2) 0.007(3) C14 0.042(3) 0.047(3) 0.041(3) 0.003(2) 0.002(2) -0.002(2) C15 0.036(3) 0.053(4) 0.037(3) -0.002(3) -0.007(2) -0.006(3) C16 0.044(3) 0.061(4) 0.034(3) -0.001(3) -0.007(2) 0.000(3) C17 0.035(3) 0.051(3) 0.036(3) -0.005(2) -0.002(2) 0.000(2) C18 0.034(3) 0.050(4) 0.036(3) 0.005(3) -0.003(2) 0.001(3) C19 0.035(3) 0.062(4) 0.060(3) 0.005(3) -0.002(2) 0.002(3) C20 0.059(4) 0.053(4) 0.067(3) 0.003(3) -0.009(3) 0.008(3) C21 0.055(4) 0.063(4) 0.055(3) 0.013(3) -0.009(3) -0.001(3) C22 0.038(3) 0.063(4) 0.051(3) 0.006(3) -0.008(2) -0.006(3) C23 0.044(3) 0.047(4) 0.044(3) 0.006(3) -0.002(2) 0.006(3) C24 0.036(3) 0.044(4) 0.041(3) 0.001(3) 0.000(2) 0.001(3) C25 0.060(3) 0.057(4) 0.052(3) 0.005(3) -0.019(2) -0.010(3) C26 0.062(3) 0.068(4) 0.051(3) 0.005(3) 0.003(3) -0.003(3) C27 0.043(3) 0.058(4) 0.055(3) 0.002(3) -0.009(2) 0.004(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 N2 1.221(4) . ? O2 N2 1.229(4) . ? O3 C2 1.373(4) . ? O3 C4 1.411(5) . ? N1 C2 1.270(5) . ? N1 C10 1.409(5) . ? N2 C15 1.470(5) . ? C2 C24 1.504(6) . ? C4 C11 1.360(5) . ? C4 C5 1.454(6) . ? C5 C6 1.403(5) . ? C5 C10 1.416(5) . ? C6 C7 1.381(5) . ? C6 H6 0.9500 . ? C7 C8 1.385(5) . ? C7 H7 0.9500 . ? C8 C9 1.368(5) . ? C8 H8 0.9500 . ? C9 C10 1.397(5) . ? C9 H9 0.9500 . ? C11 C18 1.480(5) . ? C11 C12 1.481(5) . ? C12 C13 1.387(5) . ? C12 C17 1.401(5) . ? C13 C14 1.385(5) . ? C13 H13 0.9500 . ? C14 C15 1.377(5) . ? C14 H14 0.9500 . ? C15 C16 1.365(5) . ? C16 C17 1.385(5) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 C23 1.396(5) . ? C18 C19 1.400(5) . ? C19 C20 1.379(5) . ? C19 H19 0.9500 . ? C20 C21 1.385(6) . ? C20 H20 0.9500 . ? C21 C22 1.386(6) . ? C21 H21 0.9500 . ? C22 C23 1.388(5) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? C24 C27 1.526(5) . ? C24 C26 1.533(5) . ? C24 C25 1.537(5) . ? 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 121.2(4) . . ? C2 N1 C10 118.4(4) . . ? O1 N2 O2 123.6(4) . . ? O1 N2 C15 118.3(4) . . ? O2 N2 C15 118.1(4) . . ? N1 C2 O3 123.8(5) . . ? N1 C2 C24 123.7(4) . . ? O3 C2 C24 112.3(4) . . ? C11 C4 O3 115.8(4) . . ? C11 C4 C5 130.5(5) . . ? O3 C4 C5 113.7(4) . . ? C6 C5 C10 117.0(4) . . ? C6 C5 C4 125.5(4) . . ? C10 C5 C4 117.5(5) . . ? C7 C6 C5 121.5(4) . . ? C7 C6 H6 119.2 . . ? C5 C6 H6 119.2 . . ? C6 C7 C8 120.6(5) . . ? C6 C7 H7 119.7 . . ? C8 C7 H7 119.7 . . ? C9 C8 C7 119.4(4) . . ? C9 C8 H8 120.3 . . ? C7 C8 H8 120.3 . . ? C8 C9 C10 121.1(5) . . ? C8 C9 H9 119.5 . . ? C10 C9 H9 119.5 . . ? C9 C10 N1 118.5(5) . . ? C9 C10 C5 120.4(5) . . ? N1 C10 C5 121.2(4) . . ? C4 C11 C18 120.0(4) . . ? C4 C11 C12 124.0(4) . . ? C18 C11 C12 115.9(4) . . ? C13 C12 C17 117.6(4) . . ? C13 C12 C11 123.9(4) . . ? C17 C12 C11 118.4(4) . . ? C14 C13 C12 121.4(4) . . ? C14 C13 H13 119.3 . . ? C12 C13 H13 119.3 . . ? C15 C14 C13 119.0(4) . . ? C15 C14 H14 120.5 . . ? C13 C14 H14 120.5 . . ? C16 C15 C14 121.5(4) . . ? C16 C15 N2 119.4(4) . . ? C14 C15 N2 119.1(4) . . ? C15 C16 C17 119.2(4) . . ? C15 C16 H16 120.4 . . ? C17 C16 H16 120.4 . . ? C16 C17 C12 121.2(4) . . ? C16 C17 H17 119.4 . . ? C12 C17 H17 119.4 . . ? C23 C18 C19 118.2(5) . . ? C23 C18 C11 121.4(4) . . ? C19 C18 C11 120.4(4) . . ? C20 C19 C18 120.5(5) . . ? C20 C19 H19 119.7 . . ? C18 C19 H19 119.7 . . ? C19 C20 C21 121.2(5) . . ? C19 C20 H20 119.4 . . ? C21 C20 H20 119.4 . . ? C20 C21 C22 118.7(5) . . ? C20 C21 H21 120.7 . . ? C22 C21 H21 120.7 . . ? C21 C22 C23 120.7(5) . . ? C21 C22 H22 119.6 . . ? C23 C22 H22 119.6 . . ? C22 C23 C18 120.7(4) . . ? C22 C23 H23 119.7 . . ? C18 C23 H23 119.7 . . ? C2 C24 C27 109.5(4) . . ? C2 C24 C26 107.3(4) . . ? C27 C24 C26 109.0(3) . . ? C2 C24 C25 111.1(3) . . ? C27 C24 C25 109.7(4) . . ? C26 C24 C25 110.1(4) . . ? 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 6.6(6) . . . . ? C10 N1 C2 C24 -169.0(4) . . . . ? C4 O3 C2 N1 10.1(6) . . . . ? C4 O3 C2 C24 -173.9(3) . . . . ? C2 O3 C4 C11 156.1(3) . . . . ? C2 O3 C4 C5 -22.8(5) . . . . ? C11 C4 C5 C6 20.8(7) . . . . ? O3 C4 C5 C6 -160.5(4) . . . . ? C11 C4 C5 C10 -159.0(4) . . . . ? O3 C4 C5 C10 19.6(5) . . . . ? C10 C5 C6 C7 2.5(6) . . . . ? C4 C5 C6 C7 -177.4(4) . . . . ? C5 C6 C7 C8 0.1(6) . . . . ? C6 C7 C8 C9 -1.2(6) . . . . ? C7 C8 C9 C10 -0.4(6) . . . . ? C8 C9 C10 N1 -176.1(4) . . . . ? C8 C9 C10 C5 3.1(6) . . . . ? C2 N1 C10 C9 170.4(4) . . . . ? C2 N1 C10 C5 -8.8(6) . . . . ? C6 C5 C10 C9 -4.0(6) . . . . ? C4 C5 C10 C9 175.8(4) . . . . ? C6 C5 C10 N1 175.1(4) . . . . ? C4 C5 C10 N1 -5.0(6) . . . . ? O3 C4 C11 C18 -175.6(3) . . . . ? C5 C4 C11 C18 3.0(7) . . . . ? O3 C4 C11 C12 1.8(6) . . . . ? C5 C4 C11 C12 -179.6(4) . . . . ? C4 C11 C12 C13 32.3(6) . . . . ? C18 C11 C12 C13 -150.2(4) . . . . ? C4 C11 C12 C17 -150.5(4) . . . . ? C18 C11 C12 C17 27.0(5) . . . . ? C17 C12 C13 C14 -0.5(6) . . . . ? C11 C12 C13 C14 176.8(4) . . . . ? C12 C13 C14 C15 0.7(6) . . . . ? C13 C14 C15 C16 -0.6(7) . . . . ? C13 C14 C15 N2 -179.7(4) . . . . ? O1 N2 C15 C16 -2.0(6) . . . . ? O2 N2 C15 C16 178.5(4) . . . . ? O1 N2 C15 C14 177.1(4) . . . . ? O2 N2 C15 C14 -2.4(6) . . . . ? C14 C15 C16 C17 0.2(7) . . . . ? N2 C15 C16 C17 179.3(4) . . . . ? C15 C16 C17 C12 0.1(6) . . . . ? C13 C12 C17 C16 0.0(6) . . . . ? C11 C12 C17 C16 -177.4(4) . . . . ? C4 C11 C18 C23 67.9(5) . . . . ? C12 C11 C18 C23 -109.7(4) . . . . ? C4 C11 C18 C19 -114.5(4) . . . . ? C12 C11 C18 C19 67.9(5) . . . . ? C23 C18 C19 C20 -1.3(6) . . . . ? C11 C18 C19 C20 -179.0(4) . . . . ? C18 C19 C20 C21 1.7(6) . . . . ? C19 C20 C21 C22 -1.7(7) . . . . ? C20 C21 C22 C23 1.4(6) . . . . ? C21 C22 C23 C18 -1.1(6) . . . . ? C19 C18 C23 C22 1.1(6) . . . . ? C11 C18 C23 C22 178.7(4) . . . . ? N1 C2 C24 C27 -14.1(5) . . . . ? O3 C2 C24 C27 169.9(3) . . . . ? N1 C2 C24 C26 104.1(4) . . . . ? O3 C2 C24 C26 -71.9(4) . . . . ? N1 C2 C24 C25 -135.5(4) . . . . ? O3 C2 C24 C25 48.5(4) . . . . ? _diffrn_measured_fraction_theta_max 0.929 _diffrn_reflns_theta_full 55.08 _diffrn_measured_fraction_theta_full 0.929 _refine_diff_density_max 0.196 _refine_diff_density_min -0.193 _refine_diff_density_rms 0.051