data_ryan1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Ryan' _chemical_melting_point ? _chemical_formula_moiety 'C26 H39 N O7' _chemical_formula_sum 'C26 H39 N O7' _chemical_formula_weight 477.58 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 12.015(2) _cell_length_b 12.534(2) _cell_length_c 16.724(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2518.7(9) _cell_formula_units_Z 4 _cell_measurement_temperature 205(2) _cell_measurement_reflns_used 12915 _cell_measurement_theta_min 4 _cell_measurement_theta_max 25 _chemical_absolute_configuration syn _exptl_crystal_description 'Thin Needle' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.259 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1032 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type 'empirical' _exptl_absorpt_correction_T_min 0.9910 _exptl_absorpt_correction_T_max 0.9955 _exptl_absorpt_process_details multiscan _exptl_special_details ; The crystal had a small twin component which was located using the CELL_NOW software package. Only the major component was used for solving and refinement. Both inversions of the molecule were tested and the final refinement yielded the lowest FlackX value. ; _diffrn_ambient_temperature 205(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 'area detector CCD' _diffrn_measurement_method 'thin slice 360deg phi scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12915 _diffrn_reflns_av_R_equivalents 0.0458 _diffrn_reflns_av_sigmaI/netI 0.0663 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5698 _reflns_number_gt 4924 _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^)+(0.0976P)^2^+1.1942P] 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 0.5(19) _refine_ls_number_reflns 5698 _refine_ls_number_parameters 325 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1123 _refine_ls_R_factor_gt 0.0997 _refine_ls_wR_factor_ref 0.2278 _refine_ls_wR_factor_gt 0.2211 _refine_ls_goodness_of_fit_ref 1.257 _refine_ls_restrained_S_all 1.257 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.0686(2) 0.4824(2) -0.00028(16) 0.0292(7) Uani 1 1 d . . . N1 N -0.1055(3) 0.3212(3) 0.06496(19) 0.0276(8) Uani 1 1 d . . . C1 C 0.0265(4) 0.5844(4) 0.0271(2) 0.0296(10) Uani 1 1 d . . . H1 H 0.083(3) 0.620(3) 0.041(2) 0.009(9) Uiso 1 1 d . . . H1N H -0.117(3) 0.292(3) 0.020(2) 0.003(8) Uiso 1 1 d . . . O2 O -0.2128(3) 0.6286(3) 0.06327(17) 0.0403(8) Uani 1 1 d . . . H2OH H -0.2539 0.6816 0.0592 0.048 Uiso 1 1 calc R . . C2 C -0.0010(3) 0.4876(4) 0.0704(2) 0.0293(9) Uani 1 1 d . . . H2 H 0.039(3) 0.464(3) 0.113(2) 0.003(8) Uiso 1 1 d . . . O3 O 0.1657(3) 0.6836(3) -0.08341(19) 0.0426(8) Uani 1 1 d . . . C3 C -0.1132(3) 0.4376(3) 0.0641(2) 0.0249(9) Uani 1 1 d . . . H3 H -0.1576 0.4602 0.1110 0.030 Uiso 1 1 calc R . . O4 O 0.1001(3) 0.5556(3) -0.37333(19) 0.0415(8) Uani 1 1 d . . . C4 C -0.1733(3) 0.4753(3) -0.0112(2) 0.0247(8) Uani 1 1 d . . . H4A H -0.2498 0.4483 -0.0111 0.030 Uiso 1 1 calc R . . H4B H -0.1354 0.4470 -0.0586 0.030 Uiso 1 1 calc R . . O5 O 0.1553(3) 0.7236(3) -0.40759(18) 0.0372(8) Uani 1 1 d . . . C5 C -0.1746(3) 0.5976(3) -0.0147(2) 0.0264(9) Uani 1 1 d . . . O6 O -0.0651(3) 0.3112(3) 0.19638(16) 0.0382(8) Uani 1 1 d . . . C6 C -0.2543(3) 0.6377(4) -0.0777(3) 0.0340(10) Uani 1 1 d . . . H6A H -0.2642 0.7147 -0.0706 0.041 Uiso 1 1 calc R . . H6B H -0.3268 0.6037 -0.0694 0.041 Uiso 1 1 calc R . . O7 O -0.0770(3) 0.1634(2) 0.11740(17) 0.0397(8) Uani 1 1 d . . . C7 C -0.2164(3) 0.6165(4) -0.1636(2) 0.0299(9) Uani 1 1 d . . . H7A H -0.2117 0.5395 -0.1728 0.036 Uiso 1 1 calc R . . H7B H -0.2710 0.6461 -0.2010 0.036 Uiso 1 1 calc R . . C8 C -0.1030(3) 0.6676(3) -0.1782(2) 0.0254(8) Uani 1 1 d . . . H8 H -0.1095 0.7458 -0.1709 0.031 Uiso 1 1 calc R . . C9 C -0.0184(3) 0.6228(3) -0.1163(2) 0.0201(8) Uani 1 1 d . . . H9 H -0.0207 0.5444 -0.1233 0.024 Uiso 1 1 calc R . . C10 C -0.0543(4) 0.6427(3) -0.0278(2) 0.0292(9) Uani 1 1 d . . . C11 C 0.1027(3) 0.6551(3) -0.1348(3) 0.0277(9) Uani 1 1 d . . . C12 C 0.1405(3) 0.6442(4) -0.2199(2) 0.0291(9) Uani 1 1 d . . . H12A H 0.1501 0.5684 -0.2327 0.035 Uiso 1 1 calc R . . H12B H 0.2128 0.6794 -0.2263 0.035 Uiso 1 1 calc R . . C13 C 0.0561(3) 0.6941(3) -0.2787(2) 0.0247(8) Uani 1 1 d . . . C14 C -0.0587(3) 0.6448(3) -0.2624(2) 0.0251(8) Uani 1 1 d . . . H14 H -0.0493 0.5665 -0.2663 0.030 Uiso 1 1 calc R . . C15 C -0.1290(4) 0.6787(5) -0.3352(3) 0.0453(13) Uani 1 1 d . . . H15A H -0.1864 0.6254 -0.3470 0.054 Uiso 1 1 calc R . . H15B H -0.1649 0.7477 -0.3256 0.054 Uiso 1 1 calc R . . C16 C -0.0445(4) 0.6865(5) -0.4042(3) 0.0471(13) Uani 1 1 d . . . H16A H -0.0469 0.7576 -0.4285 0.056 Uiso 1 1 calc R . . H16B H -0.0612 0.6334 -0.4454 0.056 Uiso 1 1 calc R . . C17 C 0.0710(3) 0.6653(4) -0.3670(3) 0.0323(10) Uani 1 1 d . . . C18 C 0.0573(5) 0.8162(4) -0.2676(3) 0.0435(12) Uani 1 1 d . . . H18A H -0.0011 0.8479 -0.2999 0.065 Uiso 1 1 calc R . . H18B H 0.1289 0.8442 -0.2842 0.065 Uiso 1 1 calc R . . H18C H 0.0447 0.8333 -0.2117 0.065 Uiso 1 1 calc R . . C19 C -0.0511(5) 0.7624(4) -0.0064(3) 0.0415(11) Uani 1 1 d . . . H19A H -0.0649 0.7711 0.0503 0.062 Uiso 1 1 calc R . . H19B H -0.1080 0.7998 -0.0366 0.062 Uiso 1 1 calc R . . H19C H 0.0214 0.7914 -0.0197 0.062 Uiso 1 1 calc R . . C20 C 0.2453(4) 0.6532(5) -0.4210(3) 0.0484(13) Uani 1 1 d . . . H20A H 0.2983 0.6554 -0.3765 0.058 Uiso 1 1 calc R . . H20B H 0.2844 0.6709 -0.4707 0.058 Uiso 1 1 calc R . . C21 C 0.1902(4) 0.5459(4) -0.4266(3) 0.0447(12) Uani 1 1 d . . . H21A H 0.1643 0.5316 -0.4812 0.054 Uiso 1 1 calc R . . H21B H 0.2409 0.4888 -0.4100 0.054 Uiso 1 1 calc R . . C22 C -0.0801(3) 0.2700(3) 0.1327(2) 0.0237(8) Uani 1 1 d . . . C23 C -0.0529(5) 0.0891(4) 0.1836(3) 0.0419(12) Uani 1 1 d . . . C24 C -0.0603(7) -0.0195(4) 0.1425(4) 0.0673(19) Uani 1 1 d . . . H24A H -0.1358 -0.0312 0.1240 0.101 Uiso 1 1 calc R . . H24B H -0.0400 -0.0751 0.1802 0.101 Uiso 1 1 calc R . . H24C H -0.0097 -0.0212 0.0973 0.101 Uiso 1 1 calc R . . C25 C 0.0623(5) 0.1077(5) 0.2169(4) 0.0632(17) Uani 1 1 d . . . H25A H 0.1144 0.1180 0.1733 0.095 Uiso 1 1 calc R . . H25B H 0.0848 0.0464 0.2484 0.095 Uiso 1 1 calc R . . H25C H 0.0617 0.1708 0.2506 0.095 Uiso 1 1 calc R . . C26 C -0.1439(5) 0.0972(5) 0.2460(3) 0.0536(15) Uani 1 1 d . . . H26A H -0.1277 0.1558 0.2820 0.080 Uiso 1 1 calc R . . H26B H -0.1475 0.0311 0.2761 0.080 Uiso 1 1 calc R . . H26C H -0.2147 0.1097 0.2198 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 0.0211(13) 0.0393(17) 0.0272(14) 0.0054(13) -0.0034(11) 0.0040(13) N1 0.042(2) 0.0277(18) 0.0132(15) -0.0063(13) 0.0052(14) 0.0007(16) C1 0.031(2) 0.035(2) 0.023(2) -0.0011(17) -0.0053(16) -0.012(2) O2 0.050(2) 0.0401(19) 0.0308(16) 0.0000(14) 0.0137(14) 0.0229(16) C2 0.028(2) 0.044(3) 0.0161(18) 0.0032(17) -0.0050(15) 0.0061(19) O3 0.0325(16) 0.054(2) 0.0409(18) 0.0059(16) -0.0134(14) -0.0207(16) C3 0.030(2) 0.025(2) 0.0194(18) 0.0015(15) 0.0057(16) 0.0066(17) O4 0.0469(19) 0.0394(19) 0.0381(17) -0.0013(14) 0.0139(15) -0.0005(16) C4 0.0190(17) 0.029(2) 0.0262(19) -0.0017(17) 0.0034(15) -0.0031(16) O5 0.0340(17) 0.0424(19) 0.0353(16) 0.0132(14) 0.0126(13) 0.0072(15) C5 0.029(2) 0.027(2) 0.0229(19) 0.0025(16) 0.0048(16) 0.0123(17) O6 0.054(2) 0.0412(18) 0.0190(13) 0.0018(13) -0.0032(13) 0.0069(17) C6 0.023(2) 0.039(3) 0.040(2) 0.009(2) 0.0084(18) 0.014(2) O7 0.067(2) 0.0276(16) 0.0241(14) 0.0064(12) 0.0032(15) 0.0108(16) C7 0.0208(19) 0.040(2) 0.029(2) 0.0092(19) -0.0011(16) 0.0071(19) C8 0.0180(17) 0.024(2) 0.034(2) 0.0037(16) 0.0008(16) 0.0006(17) C9 0.0190(17) 0.0178(18) 0.0236(18) 0.0023(15) -0.0015(14) -0.0014(15) C10 0.041(2) 0.024(2) 0.0231(19) -0.0057(15) 0.0036(17) -0.0039(19) C11 0.0196(18) 0.027(2) 0.036(2) 0.0088(17) -0.0106(17) -0.0007(17) C12 0.0142(17) 0.043(3) 0.030(2) 0.0090(19) -0.0021(15) 0.0001(18) C13 0.0175(17) 0.026(2) 0.0310(19) 0.0072(16) 0.0073(15) 0.0015(17) C14 0.0149(17) 0.031(2) 0.0294(19) 0.0023(17) 0.0001(15) -0.0035(17) C15 0.025(2) 0.071(4) 0.039(2) 0.020(2) -0.0045(18) 0.007(2) C16 0.032(2) 0.079(4) 0.030(2) 0.014(2) -0.0001(19) 0.001(3) C17 0.024(2) 0.040(2) 0.033(2) 0.0075(19) 0.0029(17) 0.0094(19) C18 0.050(3) 0.032(3) 0.048(3) 0.009(2) 0.013(2) -0.005(2) C19 0.058(3) 0.028(2) 0.038(2) -0.0093(19) 0.006(2) 0.001(2) C20 0.034(2) 0.059(3) 0.053(3) 0.016(3) 0.019(2) 0.007(2) C21 0.045(3) 0.051(3) 0.038(3) -0.004(2) 0.005(2) 0.001(3) C22 0.0218(19) 0.039(2) 0.0105(15) 0.0009(15) 0.0085(14) 0.0081(17) C23 0.052(3) 0.032(3) 0.042(3) 0.012(2) -0.003(2) 0.013(2) C24 0.108(5) 0.034(3) 0.060(4) 0.012(3) -0.006(4) 0.019(4) C25 0.051(3) 0.066(4) 0.072(4) 0.024(3) -0.004(3) 0.020(3) C26 0.056(3) 0.057(4) 0.048(3) 0.028(3) 0.004(3) 0.014(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 C1 1.449(6) . ? O1 C2 1.450(5) . ? N1 C22 1.338(5) . ? N1 C3 1.462(5) . ? C1 C2 1.451(6) . ? C1 C10 1.523(6) . ? O2 C5 1.436(5) . ? C2 C3 1.490(6) . ? O3 C11 1.200(5) . ? C3 C4 1.526(5) . ? O4 C21 1.408(6) . ? O4 C17 1.423(6) . ? C4 C5 1.534(6) . ? O5 C20 1.414(6) . ? O5 C17 1.421(5) . ? C5 C6 1.510(6) . ? C5 C10 1.568(6) . ? O6 C22 1.197(5) . ? C6 C7 1.529(6) . ? O7 C22 1.361(5) . ? O7 C23 1.475(5) . ? C7 C8 1.525(6) . ? C8 C14 1.532(6) . ? C8 C9 1.556(5) . ? C9 C11 1.542(5) . ? C9 C10 1.561(5) . ? C10 C19 1.543(6) . ? C11 C12 1.501(6) . ? C12 C13 1.545(5) . ? C13 C17 1.531(6) . ? C13 C14 1.536(5) . ? C13 C18 1.541(6) . ? C14 C15 1.541(6) . ? C15 C16 1.540(6) . ? C16 C17 1.544(6) . ? C20 C21 1.502(8) . ? C23 C25 1.511(8) . ? C23 C26 1.514(8) . ? C23 C24 1.527(8) . ? 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 C1 O1 C2 60.1(3) . . ? C22 N1 C3 120.1(3) . . ? O1 C1 C2 60.0(3) . . ? O1 C1 C10 117.1(3) . . ? C2 C1 C10 123.8(4) . . ? O1 C2 C1 59.9(3) . . ? O1 C2 C3 116.5(3) . . ? C1 C2 C3 121.5(4) . . ? N1 C3 C2 111.2(4) . . ? N1 C3 C4 110.3(3) . . ? C2 C3 C4 110.9(3) . . ? C21 O4 C17 108.7(4) . . ? C3 C4 C5 110.2(3) . . ? C20 O5 C17 107.5(3) . . ? O2 C5 C6 109.9(3) . . ? O2 C5 C4 103.9(3) . . ? C6 C5 C4 111.4(4) . . ? O2 C5 C10 109.0(3) . . ? C6 C5 C10 111.5(3) . . ? C4 C5 C10 110.9(3) . . ? C5 C6 C7 114.2(3) . . ? C22 O7 C23 118.9(3) . . ? C8 C7 C6 110.1(4) . . ? C7 C8 C14 112.3(3) . . ? C7 C8 C9 109.0(3) . . ? C14 C8 C9 108.5(3) . . ? C11 C9 C8 112.9(3) . . ? C11 C9 C10 114.1(3) . . ? C8 C9 C10 113.1(3) . . ? C1 C10 C19 108.1(4) . . ? C1 C10 C9 108.6(3) . . ? C19 C10 C9 111.6(3) . . ? C1 C10 C5 109.3(3) . . ? C19 C10 C5 109.9(4) . . ? C9 C10 C5 109.3(3) . . ? O3 C11 C12 121.0(4) . . ? O3 C11 C9 122.1(4) . . ? C12 C11 C9 116.9(3) . . ? C11 C12 C13 111.6(3) . . ? C17 C13 C14 100.4(3) . . ? C17 C13 C18 110.4(3) . . ? C14 C13 C18 112.7(4) . . ? C17 C13 C12 116.2(3) . . ? C14 C13 C12 108.3(3) . . ? C18 C13 C12 108.6(4) . . ? C8 C14 C13 113.5(3) . . ? C8 C14 C15 118.9(3) . . ? C13 C14 C15 104.0(3) . . ? C16 C15 C14 104.4(3) . . ? C15 C16 C17 106.2(3) . . ? O5 C17 O4 106.6(3) . . ? O5 C17 C13 115.0(4) . . ? O4 C17 C13 109.1(3) . . ? O5 C17 C16 111.1(3) . . ? O4 C17 C16 110.9(4) . . ? C13 C17 C16 104.1(3) . . ? O5 C20 C21 103.4(4) . . ? O4 C21 C20 102.8(4) . . ? O6 C22 N1 125.5(4) . . ? O6 C22 O7 126.0(4) . . ? N1 C22 O7 108.5(3) . . ? O7 C23 C25 111.1(4) . . ? O7 C23 C26 109.4(4) . . ? C25 C23 C26 113.4(5) . . ? O7 C23 C24 102.3(4) . . ? C25 C23 C24 110.9(5) . . ? C26 C23 C24 109.1(5) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2OH O3 0.83 1.99 2.789(5) 162.2 3_465 N1 H1N O5 0.85(4) 2.12(4) 2.963(4) 176(3) 4_544 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.443 _refine_diff_density_min -0.328 _refine_diff_density_rms 0.079