data_lar30 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H27 N O4' _chemical_formula_weight 429.50 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/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 9.037(3) _cell_length_b 19.075(5) _cell_length_c 13.320(4) _cell_angle_alpha 90.00 _cell_angle_beta 98.377(5) _cell_angle_gamma 90.00 _cell_volume 2271.6(11) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 958 _cell_measurement_theta_min 2.77 _cell_measurement_theta_max 23.33 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.256 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 912 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9513 _exptl_absorpt_correction_T_max 0.9736 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 14509 _diffrn_reflns_av_R_equivalents 0.0520 _diffrn_reflns_av_sigmaI/netI 0.0436 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 23.26 _reflns_number_total 3254 _reflns_number_gt 2380 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0623P)^2^+0.7557P] 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 3254 _refine_ls_number_parameters 293 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0741 _refine_ls_R_factor_gt 0.0488 _refine_ls_wR_factor_ref 0.1278 _refine_ls_wR_factor_gt 0.1141 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.086 _refine_ls_shift/su_max 0.004 _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 0.2433(3) 0.53295(14) 1.3148(2) 0.0359(7) Uani 1 1 d . . . H1 H 0.3029 0.5738 1.3132 0.043 Uiso 1 1 calc R . . C2 C 0.1127(3) 0.53591(16) 1.3580(2) 0.0413(8) Uani 1 1 d . . . H2 H 0.0826 0.5789 1.3849 0.050 Uiso 1 1 calc R . . C3 C 0.0267(3) 0.47687(16) 1.3623(2) 0.0393(7) Uani 1 1 d . . . H3 H -0.0622 0.4788 1.3925 0.047 Uiso 1 1 calc R . . C4 C 0.0703(3) 0.41487(15) 1.3223(2) 0.0355(7) Uani 1 1 d . . . H4 H 0.0109 0.3740 1.3249 0.043 Uiso 1 1 calc R . . C5 C 0.1995(3) 0.41144(15) 1.27830(19) 0.0327(7) Uani 1 1 d . . . H5 H 0.2283 0.3683 1.2511 0.039 Uiso 1 1 calc R . . C6 C 0.2876(3) 0.47084(14) 1.27371(17) 0.0258(6) Uani 1 1 d . . . C7 C 0.4466(3) 0.44117(13) 1.15496(19) 0.0230(6) Uani 1 1 d . . . C8 C 0.5852(3) 0.43764(13) 1.11076(18) 0.0240(6) Uani 1 1 d . . . C9 C 0.7264(3) 0.46214(13) 1.1470(2) 0.0315(7) Uani 1 1 d . . . H9 H 0.7477 0.4824 1.2127 0.038 Uiso 1 1 calc R . . C10 C 0.8363(3) 0.45646(14) 1.0853(2) 0.0352(7) Uani 1 1 d . . . H10 H 0.9351 0.4720 1.1089 0.042 Uiso 1 1 calc R . . C11 C 0.8020(3) 0.42791(14) 0.9887(2) 0.0331(7) Uani 1 1 d . . . H11 H 0.8773 0.4267 0.9458 0.040 Uiso 1 1 calc R . . C12 C 0.6628(3) 0.40139(13) 0.9532(2) 0.0287(6) Uani 1 1 d . . . H12 H 0.6422 0.3808 0.8877 0.034 Uiso 1 1 calc R . . C13 C 0.5528(3) 0.40563(12) 1.01618(18) 0.0226(6) Uani 1 1 d . . . C14 C 0.3949(3) 0.38609(12) 1.00180(18) 0.0232(6) Uani 1 1 d . . . C15 C 0.3061(3) 0.35489(13) 0.92637(18) 0.0245(6) Uani 1 1 d . . . C16 C 0.1387(3) 0.35115(14) 0.9203(2) 0.0314(7) Uani 1 1 d . . . H16A H 0.0926 0.3730 0.8558 0.038 Uiso 1 1 calc R . . H16B H 0.1085 0.3792 0.9765 0.038 Uiso 1 1 calc R . . C17 C 0.0770(3) 0.27798(16) 0.9258(3) 0.0499(9) Uani 1 1 d . . . H17A H -0.0336 0.2798 0.9111 0.060 Uiso 1 1 calc R . . H17B H 0.1129 0.2486 0.8730 0.060 Uiso 1 1 calc R . . C18 C 0.1221(4) 0.2447(2) 1.0273(3) 0.0846(14) Uani 1 1 d . . . H18A H 0.2311 0.2398 1.0401 0.127 Uiso 1 1 calc R . . H18B H 0.0756 0.1983 1.0281 0.127 Uiso 1 1 calc R . . H18C H 0.0890 0.2742 1.0800 0.127 Uiso 1 1 calc R . . C19 C 0.3776(3) 0.32382(13) 0.84241(18) 0.0251(6) Uani 1 1 d . . . C20 C 0.4642(3) 0.26385(13) 0.86031(19) 0.0275(6) Uani 1 1 d . . . H20 H 0.4717 0.2407 0.9240 0.033 Uiso 1 1 calc R . . C21 C 0.5399(3) 0.23766(13) 0.78481(19) 0.0262(6) Uani 1 1 d . . . C22 C 0.6416(3) 0.14242(15) 0.8882(2) 0.0424(8) Uani 1 1 d . . . H22A H 0.6854 0.1737 0.9430 0.064 Uiso 1 1 calc R . . H22B H 0.7067 0.1016 0.8854 0.064 Uiso 1 1 calc R . . H22C H 0.5428 0.1268 0.9012 0.064 Uiso 1 1 calc R . . C23 C 0.5320(3) 0.27265(13) 0.69229(18) 0.0246(6) Uani 1 1 d . . . C24 C 0.7628(3) 0.24676(16) 0.6340(2) 0.0427(8) Uani 1 1 d . . . H24A H 0.7995 0.2937 0.6546 0.064 Uiso 1 1 calc R . . H24B H 0.8023 0.2328 0.5723 0.064 Uiso 1 1 calc R . . H24C H 0.7961 0.2133 0.6884 0.064 Uiso 1 1 calc R . . C25 C 0.4429(3) 0.33228(13) 0.67405(18) 0.0254(6) Uani 1 1 d . . . C26 C 0.3574(3) 0.42605(15) 0.5619(2) 0.0397(7) Uani 1 1 d . . . H26A H 0.2514 0.4162 0.5642 0.060 Uiso 1 1 calc R . . H26B H 0.3693 0.4443 0.4948 0.060 Uiso 1 1 calc R . . H26C H 0.3933 0.4609 0.6139 0.060 Uiso 1 1 calc R . . C27 C 0.3644(3) 0.35696(14) 0.74844(18) 0.0275(6) Uani 1 1 d . . . H27 H 0.3012 0.3967 0.7353 0.033 Uiso 1 1 calc R . . N1 N 0.4277(2) 0.47018(11) 1.23790(15) 0.0277(5) Uani 1 1 d . . . O1 O 0.33502(17) 0.41060(9) 1.08832(12) 0.0252(4) Uani 1 1 d . . . O2 O 0.6270(2) 0.17881(9) 0.79419(13) 0.0357(5) Uani 1 1 d . . . O3 O 0.6031(2) 0.24752(9) 0.61465(12) 0.0339(5) Uani 1 1 d . . . O4 O 0.44204(19) 0.36285(9) 0.58087(12) 0.0321(5) 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 0.0392(17) 0.0309(16) 0.0391(17) -0.0052(13) 0.0106(14) 0.0001(13) C2 0.0398(18) 0.0445(19) 0.0423(18) -0.0138(14) 0.0148(15) 0.0065(15) C3 0.0310(17) 0.056(2) 0.0330(17) -0.0052(15) 0.0107(13) 0.0015(15) C4 0.0367(17) 0.0401(18) 0.0299(16) -0.0001(13) 0.0058(14) -0.0059(14) C5 0.0395(17) 0.0347(16) 0.0250(15) -0.0043(13) 0.0085(13) 0.0027(14) C6 0.0301(15) 0.0324(15) 0.0143(13) -0.0025(11) 0.0014(11) 0.0023(12) C7 0.0231(14) 0.0228(14) 0.0220(14) 0.0013(11) -0.0008(12) 0.0021(11) C8 0.0252(15) 0.0213(14) 0.0253(15) 0.0053(11) 0.0030(12) 0.0049(11) C9 0.0308(16) 0.0289(16) 0.0348(16) 0.0012(12) 0.0052(13) 0.0042(12) C10 0.0242(15) 0.0312(16) 0.0496(19) 0.0082(14) 0.0038(14) -0.0004(12) C11 0.0248(16) 0.0343(17) 0.0424(18) 0.0111(14) 0.0124(13) 0.0080(13) C12 0.0289(16) 0.0276(15) 0.0316(15) 0.0058(12) 0.0107(13) 0.0092(12) C13 0.0239(14) 0.0213(14) 0.0234(14) 0.0060(11) 0.0060(11) 0.0064(11) C14 0.0260(14) 0.0245(14) 0.0210(14) -0.0006(11) 0.0100(12) 0.0060(12) C15 0.0270(15) 0.0272(15) 0.0198(14) 0.0013(12) 0.0049(12) 0.0086(12) C16 0.0260(15) 0.0418(17) 0.0264(15) -0.0041(13) 0.0043(12) 0.0071(13) C17 0.0347(18) 0.047(2) 0.071(2) -0.0088(17) 0.0182(17) -0.0008(15) C18 0.040(2) 0.083(3) 0.131(4) 0.059(3) 0.013(2) 0.002(2) C19 0.0243(14) 0.0277(15) 0.0234(15) -0.0030(11) 0.0043(11) 0.0015(12) C20 0.0315(15) 0.0285(15) 0.0238(14) -0.0004(12) 0.0084(12) 0.0012(12) C21 0.0292(15) 0.0239(15) 0.0268(15) -0.0024(12) 0.0083(12) 0.0034(12) C22 0.061(2) 0.0355(17) 0.0332(17) 0.0064(14) 0.0137(15) 0.0169(15) C23 0.0269(15) 0.0275(15) 0.0212(14) -0.0068(12) 0.0091(12) -0.0008(12) C24 0.0423(19) 0.0483(19) 0.0417(18) 0.0012(15) 0.0202(15) 0.0053(15) C25 0.0318(15) 0.0277(15) 0.0171(14) -0.0015(11) 0.0044(12) -0.0036(12) C26 0.0522(19) 0.0400(18) 0.0268(16) 0.0039(13) 0.0052(14) 0.0103(15) C27 0.0280(15) 0.0294(15) 0.0246(15) -0.0025(12) 0.0018(12) 0.0070(12) N1 0.0300(13) 0.0308(12) 0.0227(12) -0.0037(10) 0.0052(10) 0.0031(10) O1 0.0232(10) 0.0334(10) 0.0201(9) -0.0044(8) 0.0066(8) 0.0024(8) O2 0.0521(12) 0.0279(11) 0.0306(11) 0.0031(8) 0.0177(9) 0.0150(9) O3 0.0417(12) 0.0379(11) 0.0244(10) -0.0066(9) 0.0125(9) 0.0050(9) O4 0.0420(12) 0.0355(11) 0.0193(10) 0.0003(8) 0.0058(8) 0.0064(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 C6 1.388(4) . ? C1 C2 1.388(4) . ? C1 H1 0.9500 . ? C2 C3 1.374(4) . ? C2 H2 0.9500 . ? C3 C4 1.378(4) . ? C3 H3 0.9500 . ? C4 C5 1.382(4) . ? C4 H4 0.9500 . ? C5 C6 1.391(4) . ? C5 H5 0.9500 . ? C6 N1 1.417(3) . ? C7 N1 1.269(3) . ? C7 O1 1.373(3) . ? C7 C8 1.461(3) . ? C8 C9 1.379(4) . ? C8 C13 1.392(3) . ? C9 C10 1.383(4) . ? C9 H9 0.9500 . ? C10 C11 1.390(4) . ? C10 H10 0.9500 . ? C11 C12 1.374(4) . ? C11 H11 0.9500 . ? C12 C13 1.393(3) . ? C12 H12 0.9500 . ? C13 C14 1.461(3) . ? C14 C15 1.331(3) . ? C14 O1 1.421(3) . ? C15 C19 1.493(3) . ? C15 C16 1.505(3) . ? C16 C17 1.509(4) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.495(5) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 C20 1.387(3) . ? C19 C27 1.392(3) . ? C20 C21 1.389(3) . ? C20 H20 0.9500 . ? C21 O2 1.366(3) . ? C21 C23 1.394(3) . ? C22 O2 1.421(3) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 O3 1.380(3) . ? C23 C25 1.394(4) . ? C24 O3 1.429(3) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 O4 1.370(3) . ? C25 C27 1.383(3) . ? C26 O4 1.431(3) . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 H27 0.9500 . ? 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 C6 C1 C2 120.7(3) . . ? C6 C1 H1 119.7 . . ? C2 C1 H1 119.7 . . ? C3 C2 C1 120.3(3) . . ? C3 C2 H2 119.9 . . ? C1 C2 H2 119.9 . . ? C2 C3 C4 119.5(3) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C3 C4 C5 120.8(3) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.6 . . ? C4 C5 C6 120.3(3) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C1 C6 C5 118.6(2) . . ? C1 C6 N1 117.6(2) . . ? C5 C6 N1 123.6(2) . . ? N1 C7 O1 124.7(2) . . ? N1 C7 C8 127.1(2) . . ? O1 C7 C8 108.2(2) . . ? C9 C8 C13 121.8(2) . . ? C9 C8 C7 130.3(2) . . ? C13 C8 C7 107.8(2) . . ? C8 C9 C10 118.3(3) . . ? C8 C9 H9 120.9 . . ? C10 C9 H9 120.9 . . ? C9 C10 C11 119.9(3) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? C12 C11 C10 122.2(2) . . ? C12 C11 H11 118.9 . . ? C10 C11 H11 118.9 . . ? C11 C12 C13 118.0(3) . . ? C11 C12 H12 121.0 . . ? C13 C12 H12 121.0 . . ? C8 C13 C12 119.7(2) . . ? C8 C13 C14 107.6(2) . . ? C12 C13 C14 132.5(2) . . ? C15 C14 O1 120.0(2) . . ? C15 C14 C13 133.1(2) . . ? O1 C14 C13 106.8(2) . . ? C14 C15 C19 117.7(2) . . ? C14 C15 C16 123.5(2) . . ? C19 C15 C16 118.8(2) . . ? C15 C16 C17 114.7(2) . . ? C15 C16 H16A 108.6 . . ? C17 C16 H16A 108.6 . . ? C15 C16 H16B 108.6 . . ? C17 C16 H16B 108.6 . . ? H16A C16 H16B 107.6 . . ? C18 C17 C16 112.5(3) . . ? C18 C17 H17A 109.1 . . ? C16 C17 H17A 109.1 . . ? C18 C17 H17B 109.1 . . ? C16 C17 H17B 109.1 . . ? H17A C17 H17B 107.8 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C20 C19 C27 120.1(2) . . ? C20 C19 C15 119.6(2) . . ? C27 C19 C15 120.3(2) . . ? C19 C20 C21 119.8(2) . . ? C19 C20 H20 120.1 . . ? C21 C20 H20 120.1 . . ? O2 C21 C20 124.6(2) . . ? O2 C21 C23 115.4(2) . . ? C20 C21 C23 120.0(2) . . ? O2 C22 H22A 109.5 . . ? O2 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O2 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? O3 C23 C21 121.8(2) . . ? O3 C23 C25 118.2(2) . . ? C21 C23 C25 119.9(2) . . ? O3 C24 H24A 109.5 . . ? O3 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? O3 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? O4 C25 C27 124.6(2) . . ? O4 C25 C23 115.6(2) . . ? C27 C25 C23 119.8(2) . . ? O4 C26 H26A 109.5 . . ? O4 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? O4 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C25 C27 C19 120.3(2) . . ? C25 C27 H27 119.8 . . ? C19 C27 H27 119.8 . . ? C7 N1 C6 122.5(2) . . ? C7 O1 C14 109.48(18) . . ? C21 O2 C22 117.41(19) . . ? C23 O3 C24 115.9(2) . . ? C25 O4 C26 116.78(19) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 23.26 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.191 _refine_diff_density_min -0.232 _refine_diff_density_rms 0.049