# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Rives, Arnaud' 'Baudoin-Dehoux, Cecile' 'Saffon, Nathalie' 'Andrieu-Abadie, Nathalie' 'Genisson, Yves' _publ_contact_author_name 'Genisson, Yves' _publ_contact_author_email genisson@chimie.ups-tlse.fr _publ_section_title ; Asymmetric synthesis and cytotoxic activity of isomeric phytosphingosine derivatives ; # Attachment '- Genisson-OBC-RX.CIF' data_7 _database_code_depnum_ccdc_archive 'CCDC 836021' #TrackingRef '- Genisson-OBC-RX.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H45 N O3' _chemical_formula_weight 407.62 _chemical_absolute_configuration syn 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 P2(1)2(1)2(1) 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 4.9152(2) _cell_length_b 9.6665(4) _cell_length_c 50.7258(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2410.12(16) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 1913 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 20.96 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.123 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 904 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.981 _exptl_absorpt_correction_T_max 0.997 _exptl_absorpt_process_details 'SADABS (Bruker-AXS)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25744 _diffrn_reflns_av_R_equivalents 0.1026 _diffrn_reflns_av_sigmaI/netI 0.0772 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -61 _diffrn_reflns_limit_l_max 57 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 25.35 _reflns_number_total 4399 _reflns_number_gt 2898 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0394P)^2^+0.0704P] 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, 1774 Friedel pairs' _refine_ls_number_reflns 4399 _refine_ls_number_parameters 269 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0977 _refine_ls_R_factor_gt 0.0509 _refine_ls_wR_factor_ref 0.1049 _refine_ls_wR_factor_gt 0.0903 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _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 0.8622(6) 0.4115(3) 0.24767(5) 0.0327(7) Uani 1 1 d . . . H1A H 0.9502 0.3295 0.2397 0.039 Uiso 1 1 calc R . . H1B H 0.7367 0.4513 0.2344 0.039 Uiso 1 1 calc R . . C2 C 0.7004(6) 0.3667(2) 0.27149(5) 0.0255(6) Uani 1 1 d . . . H2 H 0.5721 0.2920 0.2659 0.031 Uiso 1 1 calc R . . C3 C 0.8787(5) 0.3106(2) 0.29375(4) 0.0204(6) Uani 1 1 d . . . H3 H 0.9910 0.3880 0.3010 0.024 Uiso 1 1 calc R . . C4 C 0.7278(5) 0.2390(2) 0.31671(4) 0.0222(6) Uani 1 1 d . . . H4 H 0.8658 0.1862 0.3271 0.027 Uiso 1 1 calc R . . C5 C 0.4509(6) 0.0272(3) 0.32454(5) 0.0276(6) Uani 1 1 d . . . H5A H 0.2880 -0.0202 0.3174 0.033 Uiso 1 1 calc R . . H5B H 0.3985 0.0705 0.3415 0.033 Uiso 1 1 calc R . . C6 C 0.6679(6) -0.0802(3) 0.32989(5) 0.0246(6) Uani 1 1 d . . . C7 C 0.7258(6) -0.1809(3) 0.31126(5) 0.0323(7) Uani 1 1 d . . . H7 H 0.6253 -0.1825 0.2953 0.039 Uiso 1 1 calc R . . C8 C 0.9252(6) -0.2786(3) 0.31531(6) 0.0388(7) Uani 1 1 d . . . H8 H 0.9624 -0.3461 0.3022 0.047 Uiso 1 1 calc R . . C9 C 1.0711(6) -0.2779(3) 0.33866(6) 0.0389(7) Uani 1 1 d . . . H9 H 1.2101 -0.3444 0.3416 0.047 Uiso 1 1 calc R . . C10 C 1.0142(6) -0.1804(3) 0.35765(5) 0.0385(8) Uani 1 1 d . . . H10 H 1.1128 -0.1807 0.3738 0.046 Uiso 1 1 calc R . . C11 C 0.8146(6) -0.0821(3) 0.35347(5) 0.0322(7) Uani 1 1 d . . . H11 H 0.7770 -0.0153 0.3667 0.039 Uiso 1 1 calc R . . C12 C 0.5857(6) 0.3396(3) 0.33563(4) 0.0263(7) Uani 1 1 d . . . H12A H 0.5293 0.4227 0.3256 0.032 Uiso 1 1 calc R . . H12B H 0.4190 0.2949 0.3425 0.032 Uiso 1 1 calc R . . C13 C 0.7616(6) 0.3849(3) 0.35886(5) 0.0293(7) Uani 1 1 d . . . H13A H 0.8023 0.3033 0.3700 0.035 Uiso 1 1 calc R . . H13B H 0.9364 0.4214 0.3521 0.035 Uiso 1 1 calc R . . C14 C 0.6265(6) 0.4950(3) 0.37573(4) 0.0292(7) Uani 1 1 d . . . H14A H 0.4460 0.4604 0.3813 0.035 Uiso 1 1 calc R . . H14B H 0.5960 0.5781 0.3647 0.035 Uiso 1 1 calc R . . C15 C 0.7852(6) 0.5375(3) 0.40012(4) 0.0306(7) Uani 1 1 d . . . H15A H 0.9707 0.5660 0.3948 0.037 Uiso 1 1 calc R . . H15B H 0.8026 0.4567 0.4120 0.037 Uiso 1 1 calc R . . C16 C 0.6500(6) 0.6563(3) 0.41514(5) 0.0327(7) Uani 1 1 d . . . H16A H 0.6287 0.7356 0.4030 0.039 Uiso 1 1 calc R . . H16B H 0.4655 0.6265 0.4205 0.039 Uiso 1 1 calc R . . C17 C 0.8011(6) 0.7052(3) 0.43936(5) 0.0319(7) Uani 1 1 d . . . H17A H 0.9879 0.7321 0.4342 0.038 Uiso 1 1 calc R . . H17B H 0.8159 0.6272 0.4519 0.038 Uiso 1 1 calc R . . C18 C 0.6682(6) 0.8263(3) 0.45325(5) 0.0335(7) Uani 1 1 d . . . H18A H 0.4777 0.8011 0.4574 0.040 Uiso 1 1 calc R . . H18B H 0.6631 0.9057 0.4410 0.040 Uiso 1 1 calc R . . C19 C 0.8076(6) 0.8720(3) 0.47853(5) 0.0316(7) Uani 1 1 d . . . H19A H 0.8077 0.7937 0.4911 0.038 Uiso 1 1 calc R . . H19B H 0.9995 0.8950 0.4745 0.038 Uiso 1 1 calc R . . C20 C 0.6750(6) 0.9959(3) 0.49162(4) 0.0351(7) Uani 1 1 d . . . H20A H 0.4816 0.9738 0.4951 0.042 Uiso 1 1 calc R . . H20B H 0.6798 1.0749 0.4792 0.042 Uiso 1 1 calc R . . C21 C 0.8075(6) 1.0401(3) 0.51738(5) 0.0321(7) Uani 1 1 d . . . H21A H 1.0014 1.0613 0.5140 0.039 Uiso 1 1 calc R . . H21B H 0.8006 0.9617 0.5299 0.039 Uiso 1 1 calc R . . C22 C 0.6749(6) 1.1657(3) 0.53021(5) 0.0354(7) Uani 1 1 d . . . H22A H 0.6849 1.2447 0.5178 0.042 Uiso 1 1 calc R . . H22B H 0.4801 1.1452 0.5333 0.042 Uiso 1 1 calc R . . C23 C 0.8046(6) 1.2080(3) 0.55618(5) 0.0350(7) Uani 1 1 d . . . H23A H 0.7924 1.1294 0.5686 0.042 Uiso 1 1 calc R . . H23B H 0.9998 1.2274 0.5531 0.042 Uiso 1 1 calc R . . C24 C 0.6751(7) 1.3337(3) 0.56876(5) 0.0453(9) Uani 1 1 d . . . H24A H 0.4797 1.3147 0.5718 0.054 Uiso 1 1 calc R . . H24B H 0.6881 1.4127 0.5564 0.054 Uiso 1 1 calc R . . C25 C 0.8069(7) 1.3742(3) 0.59484(5) 0.0564(10) Uani 1 1 d . . . H25A H 0.9985 1.3976 0.5919 0.085 Uiso 1 1 calc R . . H25B H 0.7948 1.2966 0.6072 0.085 Uiso 1 1 calc R . . H25C H 0.7122 1.4546 0.6022 0.085 Uiso 1 1 calc R . . N1 N 0.5313(5) 0.1380(2) 0.30590(4) 0.0232(5) Uani 1 1 d D . . H100 H 0.610(5) 0.101(2) 0.2927(3) 0.028 Uiso 1 1 d D . . O1 O 1.0659(4) 0.51143(19) 0.25399(3) 0.0395(5) Uani 1 1 d . . . H1 H 1.0524 0.5793 0.2437 0.059 Uiso 1 1 calc R . . O2 O 0.5444(4) 0.47863(18) 0.28198(3) 0.0371(5) Uani 1 1 d . . . H2A H 0.4059 0.4912 0.2726 0.056 Uiso 1 1 calc R . . O3 O 1.0563(4) 0.21168(17) 0.28143(3) 0.0247(4) Uani 1 1 d . . . H3A H 1.1910 0.1970 0.2912 0.037 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 C1 0.0359(19) 0.0336(15) 0.0285(15) 0.0064(13) -0.0073(15) -0.0056(15) C2 0.0218(15) 0.0220(13) 0.0326(14) -0.0029(11) -0.0043(14) -0.0002(14) C3 0.0190(16) 0.0205(12) 0.0217(13) -0.0031(11) -0.0022(12) 0.0031(12) C4 0.0171(15) 0.0264(14) 0.0230(13) -0.0003(11) -0.0034(12) 0.0007(13) C5 0.0243(15) 0.0272(13) 0.0313(14) 0.0046(12) 0.0020(13) -0.0014(14) C6 0.0195(16) 0.0266(13) 0.0276(14) 0.0075(12) 0.0042(13) -0.0074(13) C7 0.0373(19) 0.0296(15) 0.0302(15) 0.0030(12) -0.0048(15) -0.0001(15) C8 0.0435(19) 0.0279(15) 0.0450(17) 0.0042(14) 0.0065(17) -0.0006(17) C9 0.0322(18) 0.0261(15) 0.0583(19) 0.0132(15) -0.0001(17) 0.0029(16) C10 0.037(2) 0.0420(17) 0.0364(16) 0.0162(14) -0.0093(15) -0.0077(17) C11 0.0313(18) 0.0321(15) 0.0332(16) 0.0046(13) -0.0032(15) -0.0052(16) C12 0.0235(15) 0.0304(15) 0.0250(14) -0.0052(11) 0.0005(13) 0.0029(14) C13 0.0287(18) 0.0343(15) 0.0248(13) -0.0048(12) -0.0003(13) 0.0008(15) C14 0.0262(17) 0.0348(15) 0.0267(14) -0.0057(12) 0.0013(13) 0.0013(15) C15 0.0295(17) 0.0336(15) 0.0286(14) -0.0085(12) 0.0008(14) 0.0018(15) C16 0.0283(17) 0.0363(16) 0.0333(15) -0.0088(13) 0.0010(14) -0.0009(15) C17 0.0281(16) 0.0393(16) 0.0284(14) -0.0078(13) -0.0023(14) 0.0023(16) C18 0.0349(18) 0.0368(17) 0.0288(14) -0.0075(12) -0.0023(14) 0.0002(16) C19 0.0301(17) 0.0378(15) 0.0270(14) -0.0076(12) -0.0012(14) 0.0010(16) C20 0.0350(19) 0.0396(17) 0.0307(14) -0.0078(13) -0.0018(14) 0.0007(17) C21 0.0314(17) 0.0366(16) 0.0284(14) -0.0072(12) 0.0028(14) -0.0002(16) C22 0.0345(18) 0.0386(17) 0.0331(15) -0.0077(13) -0.0047(15) 0.0026(16) C23 0.0344(17) 0.0406(16) 0.0301(14) -0.0049(13) 0.0000(15) 0.0015(17) C24 0.049(2) 0.0432(19) 0.0434(18) -0.0157(15) -0.0012(17) -0.0010(18) C25 0.067(3) 0.057(2) 0.0449(18) -0.0217(16) 0.0036(19) -0.001(2) N1 0.0227(14) 0.0232(11) 0.0239(11) 0.0005(9) 0.0011(11) -0.0022(11) O1 0.0300(11) 0.0382(12) 0.0501(12) 0.0222(10) -0.0126(11) -0.0092(11) O2 0.0344(12) 0.0336(10) 0.0434(11) -0.0012(9) -0.0105(10) 0.0159(11) O3 0.0189(10) 0.0298(9) 0.0253(9) -0.0043(8) -0.0009(9) 0.0046(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 O1 1.428(3) . ? C1 C2 1.510(3) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 O2 1.429(3) . ? C2 C3 1.529(3) . ? C2 H2 1.0000 . ? C3 O3 1.438(3) . ? C3 C4 1.545(3) . ? C3 H3 1.0000 . ? C4 N1 1.479(3) . ? C4 C12 1.534(3) . ? C4 H4 1.0000 . ? C5 N1 1.482(3) . ? C5 C6 1.514(4) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.386(3) . ? C6 C11 1.397(3) . ? C7 C8 1.377(4) . ? C7 H7 0.9500 . ? C8 C9 1.385(4) . ? C8 H8 0.9500 . ? C9 C10 1.376(4) . ? C9 H9 0.9500 . ? C10 C11 1.382(4) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 C13 1.526(3) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.518(3) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.519(3) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.530(3) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.511(3) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.514(3) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.520(3) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.517(4) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C21 1.521(3) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C22 1.524(3) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 C23 1.519(3) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C24 1.513(4) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C25 1.524(4) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? N1 H100 0.852(9) . ? O1 H1 0.8400 . ? O2 H2A 0.8400 . ? O3 H3A 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 C1 C2 112.6(2) . . ? O1 C1 H1A 109.1 . . ? C2 C1 H1A 109.1 . . ? O1 C1 H1B 109.1 . . ? C2 C1 H1B 109.1 . . ? H1A C1 H1B 107.8 . . ? O2 C2 C1 111.3(2) . . ? O2 C2 C3 107.54(18) . . ? C1 C2 C3 113.0(2) . . ? O2 C2 H2 108.3 . . ? C1 C2 H2 108.3 . . ? C3 C2 H2 108.3 . . ? O3 C3 C2 105.24(17) . . ? O3 C3 C4 108.74(18) . . ? C2 C3 C4 116.1(2) . . ? O3 C3 H3 108.8 . . ? C2 C3 H3 108.8 . . ? C4 C3 H3 108.8 . . ? N1 C4 C12 110.7(2) . . ? N1 C4 C3 109.26(18) . . ? C12 C4 C3 114.0(2) . . ? N1 C4 H4 107.6 . . ? C12 C4 H4 107.6 . . ? C3 C4 H4 107.6 . . ? N1 C5 C6 115.0(2) . . ? N1 C5 H5A 108.5 . . ? C6 C5 H5A 108.5 . . ? N1 C5 H5B 108.5 . . ? C6 C5 H5B 108.5 . . ? H5A C5 H5B 107.5 . . ? C7 C6 C11 118.0(3) . . ? C7 C6 C5 120.3(2) . . ? C11 C6 C5 121.8(2) . . ? C8 C7 C6 121.8(3) . . ? C8 C7 H7 119.1 . . ? C6 C7 H7 119.1 . . ? C7 C8 C9 119.5(3) . . ? C7 C8 H8 120.2 . . ? C9 C8 H8 120.2 . . ? C10 C9 C8 119.8(3) . . ? C10 C9 H9 120.1 . . ? C8 C9 H9 120.1 . . ? C9 C10 C11 120.5(3) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C10 C11 C6 120.4(3) . . ? C10 C11 H11 119.8 . . ? C6 C11 H11 119.8 . . ? C13 C12 C4 114.0(2) . . ? C13 C12 H12A 108.7 . . ? C4 C12 H12A 108.7 . . ? C13 C12 H12B 108.7 . . ? C4 C12 H12B 108.7 . . ? H12A C12 H12B 107.6 . . ? C14 C13 C12 112.9(2) . . ? C14 C13 H13A 109.0 . . ? C12 C13 H13A 109.0 . . ? C14 C13 H13B 109.0 . . ? C12 C13 H13B 109.0 . . ? H13A C13 H13B 107.8 . . ? C13 C14 C15 115.1(2) . . ? C13 C14 H14A 108.5 . . ? C15 C14 H14A 108.5 . . ? C13 C14 H14B 108.5 . . ? C15 C14 H14B 108.5 . . ? H14A C14 H14B 107.5 . . ? C14 C15 C16 112.7(2) . . ? C14 C15 H15A 109.1 . . ? C16 C15 H15A 109.1 . . ? C14 C15 H15B 109.1 . . ? C16 C15 H15B 109.1 . . ? H15A C15 H15B 107.8 . . ? C17 C16 C15 115.2(2) . . ? C17 C16 H16A 108.5 . . ? C15 C16 H16A 108.5 . . ? C17 C16 H16B 108.5 . . ? C15 C16 H16B 108.5 . . ? H16A C16 H16B 107.5 . . ? C16 C17 C18 114.1(2) . . ? C16 C17 H17A 108.7 . . ? C18 C17 H17A 108.7 . . ? C16 C17 H17B 108.7 . . ? C18 C17 H17B 108.7 . . ? H17A C17 H17B 107.6 . . ? C17 C18 C19 115.0(2) . . ? C17 C18 H18A 108.5 . . ? C19 C18 H18A 108.5 . . ? C17 C18 H18B 108.5 . . ? C19 C18 H18B 108.5 . . ? H18A C18 H18B 107.5 . . ? C20 C19 C18 113.9(2) . . ? C20 C19 H19A 108.8 . . ? C18 C19 H19A 108.8 . . ? C20 C19 H19B 108.8 . . ? C18 C19 H19B 108.8 . . ? H19A C19 H19B 107.7 . . ? C19 C20 C21 114.4(2) . . ? C19 C20 H20A 108.6 . . ? C21 C20 H20A 108.6 . . ? C19 C20 H20B 108.6 . . ? C21 C20 H20B 108.6 . . ? H20A C20 H20B 107.6 . . ? C20 C21 C22 114.0(2) . . ? C20 C21 H21A 108.7 . . ? C22 C21 H21A 108.7 . . ? C20 C21 H21B 108.7 . . ? C22 C21 H21B 108.7 . . ? H21A C21 H21B 107.6 . . ? C23 C22 C21 113.9(2) . . ? C23 C22 H22A 108.8 . . ? C21 C22 H22A 108.8 . . ? C23 C22 H22B 108.8 . . ? C21 C22 H22B 108.8 . . ? H22A C22 H22B 107.7 . . ? C24 C23 C22 113.9(2) . . ? C24 C23 H23A 108.8 . . ? C22 C23 H23A 108.8 . . ? C24 C23 H23B 108.8 . . ? C22 C23 H23B 108.8 . . ? H23A C23 H23B 107.7 . . ? C23 C24 C25 113.2(3) . . ? C23 C24 H24A 108.9 . . ? C25 C24 H24A 108.9 . . ? C23 C24 H24B 108.9 . . ? C25 C24 H24B 108.9 . . ? H24A C24 H24B 107.8 . . ? 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 . . ? C4 N1 C5 114.48(19) . . ? C4 N1 H100 106.0(18) . . ? C5 N1 H100 108.5(16) . . ? C1 O1 H1 109.5 . . ? C2 O2 H2A 109.5 . . ? C3 O3 H3A 109.5 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.164 _refine_diff_density_min -0.153 _refine_diff_density_rms 0.039 #===END data_9 _database_code_depnum_ccdc_archive 'CCDC 836022' #TrackingRef '- Genisson-OBC-RX.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H45 N O3' _chemical_formula_weight 407.62 _chemical_absolute_configuration syn 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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.2997(5) _cell_length_b 4.9870(3) _cell_length_c 24.6551(13) _cell_angle_alpha 90.00 _cell_angle_beta 92.668(4) _cell_angle_gamma 90.00 _cell_volume 1265.03(12) _cell_formula_units_Z 2 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 4599 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 29.99 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.070 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 452 _exptl_absorpt_coefficient_mu 0.068 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.729977 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details 'SADABS (Bruker-AXS)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17243 _diffrn_reflns_av_R_equivalents 0.0388 _diffrn_reflns_av_sigmaI/netI 0.0453 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 5.13 _diffrn_reflns_theta_max 26.37 _reflns_number_total 5095 _reflns_number_gt 3682 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0552P)^2^+0.6562P] 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, 2240 Friedel pairs' _refine_ls_number_reflns 5095 _refine_ls_number_parameters 321 _refine_ls_number_restraints 169 _refine_ls_R_factor_all 0.0831 _refine_ls_R_factor_gt 0.0545 _refine_ls_wR_factor_ref 0.1557 _refine_ls_wR_factor_gt 0.1405 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.066 _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 0.2901(2) 0.5683(5) 0.01898(8) 0.0387(5) Uani 1 1 d . . . H1C H 0.343(3) 0.617(8) 0.0017(14) 0.046 Uiso 1 1 d . . . O2 O 0.53625(19) 0.3144(5) 0.04627(8) 0.0369(5) Uani 1 1 d . . . H2C H 0.587(3) 0.328(7) 0.0706(13) 0.044 Uiso 1 1 d . . . O3 O 0.37197(19) 0.5638(4) 0.12543(8) 0.0358(5) Uani 1 1 d . . . H3C H 0.331(3) 0.614(7) 0.0942(13) 0.043 Uiso 1 1 d . . . N1 N 0.6095(2) 0.3037(5) 0.15197(9) 0.0335(5) Uani 1 1 d . . . H1 H 0.619(3) 0.475(7) 0.1651(12) 0.040 Uiso 1 1 d . . . C1 C 0.3121(3) 0.2844(7) 0.01938(11) 0.0394(7) Uani 1 1 d . . . H1A H 0.3388 0.2276 -0.0169 0.047 Uiso 1 1 calc R . . H1B H 0.2298 0.1915 0.0267 0.047 Uiso 1 1 calc R . . C2 C 0.4155(3) 0.2004(6) 0.06162(10) 0.0329(6) Uani 1 1 d . . . H2A H 0.4237 0.0007 0.0602 0.040 Uiso 1 1 calc R . . C3 C 0.3828(2) 0.2788(6) 0.11926(10) 0.0300(6) Uani 1 1 d . . . H3A H 0.2969 0.1973 0.1270 0.036 Uiso 1 1 calc R . . C4 C 0.4828(2) 0.1815(6) 0.16293(10) 0.0313(6) Uani 1 1 d . . . H4 H 0.4908 -0.0178 0.1600 0.038 Uiso 1 1 calc R . . C5 C 0.4408(3) 0.2521(6) 0.22057(10) 0.0362(6) Uani 1 1 d . . . H5A H 0.5102 0.1931 0.2470 0.043 Uiso 1 1 calc R . . H5B H 0.4342 0.4497 0.2234 0.043 Uiso 1 1 calc R . . C6 C 0.3132(3) 0.1312(6) 0.23696(11) 0.0363(7) Uani 1 1 d . . . H6A H 0.3216 -0.0665 0.2382 0.044 Uiso 1 1 calc R . . H6B H 0.2441 0.1765 0.2092 0.044 Uiso 1 1 calc R . . C7 C 0.2733(3) 0.2319(6) 0.29219(11) 0.0378(7) Uani 1 1 d . . . H7A H 0.2650 0.4296 0.2907 0.045 Uiso 1 1 calc R . . H7B H 0.3434 0.1886 0.3196 0.045 Uiso 1 1 calc R . . C8 C 0.1454(3) 0.1133(6) 0.31077(11) 0.0368(7) Uani 1 1 d . . . H8A H 0.0763 0.1454 0.2823 0.044 Uiso 1 1 calc R . . H8B H 0.1556 -0.0831 0.3151 0.044 Uiso 1 1 calc R . . C9 C 0.1031(3) 0.2315(6) 0.36397(11) 0.0380(7) Uani 1 1 d . . . H9A H 0.0919 0.4275 0.3595 0.046 Uiso 1 1 calc R . . H9B H 0.1729 0.2017 0.3923 0.046 Uiso 1 1 calc R . . C10 C -0.0227(3) 0.1126(7) 0.38320(11) 0.0373(7) Uani 1 1 d . . . H10A H -0.0114 -0.0832 0.3880 0.045 Uiso 1 1 calc R . . H10B H -0.0925 0.1413 0.3548 0.045 Uiso 1 1 calc R . . C11 C -0.0654(3) 0.2334(6) 0.43653(11) 0.0371(7) Uani 1 1 d . . . H11A H 0.0050 0.2069 0.4648 0.045 Uiso 1 1 calc R . . H11B H -0.0776 0.4289 0.4316 0.045 Uiso 1 1 calc R . . C12 C -0.1901(3) 0.1137(6) 0.45649(11) 0.0357(6) Uani 1 1 d . . . H12A H -0.2603 0.1395 0.4282 0.043 Uiso 1 1 calc R . . H12B H -0.1777 -0.0817 0.4616 0.043 Uiso 1 1 calc R . . C13 C -0.2330(3) 0.2341(6) 0.50935(11) 0.0354(7) Uani 1 1 d . . . H13A H -0.2455 0.4295 0.5042 0.042 Uiso 1 1 calc R . . H13B H -0.1627 0.2087 0.5376 0.042 Uiso 1 1 calc R . . C14 C -0.3576(2) 0.1147(6) 0.52955(10) 0.0341(6) Uani 1 1 d . . . H14A H -0.3451 -0.0805 0.5349 0.041 Uiso 1 1 calc R . . H14B H -0.4281 0.1397 0.5013 0.041 Uiso 1 1 calc R . . C15 C -0.3996(3) 0.2382(6) 0.58247(10) 0.0348(6) Uani 1 1 d . . . H15A H -0.4117 0.4335 0.5771 0.042 Uiso 1 1 calc R . . H15B H -0.3291 0.2128 0.6107 0.042 Uiso 1 1 calc R . . C16 C -0.5251(3) 0.1194(6) 0.60291(11) 0.0366(7) Uani 1 1 d . . . H16A H -0.5956 0.1445 0.5747 0.044 Uiso 1 1 calc R . . H16B H -0.5130 -0.0758 0.6084 0.044 Uiso 1 1 calc R . . C17 C -0.5663(3) 0.2437(6) 0.65549(11) 0.0407(7) Uani 1 1 d . . . H17A H -0.4955 0.2191 0.6836 0.049 Uiso 1 1 calc R . . H17B H -0.5784 0.4389 0.6499 0.049 Uiso 1 1 calc R . . C18 C -0.6904(3) 0.1272(8) 0.67625(14) 0.0543(9) Uani 1 1 d . . . H18A H -0.7600 0.1411 0.6479 0.081 Uiso 1 1 calc R . . H18B H -0.7149 0.2268 0.7085 0.081 Uiso 1 1 calc R . . H18C H -0.6764 -0.0617 0.6858 0.081 Uiso 1 1 calc R . . C19 C 0.7262(3) 0.1534(7) 0.17042(15) 0.0535(9) Uani 1 1 d . A . H19A H 0.7288 -0.0211 0.1513 0.064 Uiso 1 1 calc R . . H19B H 0.7243 0.1182 0.2099 0.064 Uiso 1 1 calc R . . C20 C 0.8436(3) 0.3138(7) 0.15869(13) 0.0471(7) Uani 1 1 d DU . . C21 C 0.8824(16) 0.294(3) 0.1056(5) 0.0578(14) Uani 0.432(14) 1 d PDU A 1 H21 H 0.8423 0.1659 0.0818 0.069 Uiso 0.432(14) 1 calc PR A 1 C22 C 0.9791(11) 0.460(3) 0.0870(5) 0.0592(15) Uani 0.432(14) 1 d PDU A 1 H22 H 0.9981 0.4546 0.0496 0.071 Uiso 0.432(14) 1 calc PR A 1 C23 C 1.0475(11) 0.630(3) 0.1212(7) 0.0597(15) Uani 0.432(14) 1 d PDU A 1 H23 H 1.1155 0.7360 0.1077 0.072 Uiso 0.432(14) 1 calc PR A 1 C24 C 1.0183(11) 0.648(2) 0.1746(7) 0.0589(16) Uani 0.432(14) 1 d PDU A 1 H24 H 1.0649 0.7664 0.1986 0.071 Uiso 0.432(14) 1 calc PR A 1 C25 C 0.9192(14) 0.489(3) 0.1927(5) 0.0547(15) Uani 0.432(14) 1 d PDU A 1 H25 H 0.9006 0.4982 0.2300 0.066 Uiso 0.432(14) 1 calc PR A 1 C21' C 0.8894(12) 0.356(2) 0.1070(4) 0.0574(14) Uani 0.568(14) 1 d PDU A 2 H21' H 0.8477 0.2721 0.0763 0.069 Uiso 0.568(14) 1 calc PR A 2 C22' C 0.9975(9) 0.522(2) 0.1009(4) 0.0601(14) Uani 0.568(14) 1 d PDU A 2 H22' H 1.0325 0.5459 0.0663 0.072 Uiso 0.568(14) 1 calc PR A 2 C23' C 1.0512(8) 0.6480(17) 0.1451(6) 0.0606(15) Uani 0.568(14) 1 d PDU A 2 H23' H 1.1223 0.7663 0.1408 0.073 Uiso 0.568(14) 1 calc PR A 2 C24' C 1.0059(8) 0.610(2) 0.1961(5) 0.0597(14) Uani 0.568(14) 1 d PDU A 2 H24' H 1.0457 0.7010 0.2264 0.072 Uiso 0.568(14) 1 calc PR A 2 C25' C 0.9037(9) 0.441(2) 0.2033(3) 0.0528(14) Uani 0.568(14) 1 d PDU A 2 H25' H 0.8739 0.4100 0.2386 0.063 Uiso 0.568(14) 1 calc PR A 2 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 0.0389(11) 0.0432(13) 0.0348(11) 0.0046(10) 0.0083(8) -0.0006(10) O2 0.0394(11) 0.0409(11) 0.0314(10) -0.0002(10) 0.0128(8) -0.0024(10) O3 0.0453(11) 0.0305(11) 0.0322(10) -0.0049(9) 0.0075(8) -0.0017(9) N1 0.0290(11) 0.0317(13) 0.0405(13) -0.0008(11) 0.0075(9) -0.0020(11) C1 0.0472(16) 0.0391(17) 0.0323(14) -0.0005(13) 0.0055(12) -0.0118(15) C2 0.0408(15) 0.0277(14) 0.0309(14) -0.0001(11) 0.0091(11) -0.0025(12) C3 0.0329(13) 0.0260(14) 0.0314(13) -0.0005(11) 0.0055(10) -0.0089(12) C4 0.0334(13) 0.0293(15) 0.0319(14) -0.0053(11) 0.0102(11) -0.0084(11) C5 0.0396(14) 0.0408(18) 0.0287(13) -0.0018(12) 0.0076(11) -0.0051(13) C6 0.0369(14) 0.0429(18) 0.0293(13) -0.0015(12) 0.0044(11) -0.0038(13) C7 0.0443(15) 0.0381(17) 0.0319(14) -0.0009(12) 0.0103(12) -0.0027(13) C8 0.0390(15) 0.0394(17) 0.0325(14) 0.0005(12) 0.0058(12) -0.0024(13) C9 0.0415(15) 0.0380(17) 0.0351(14) -0.0021(12) 0.0091(12) -0.0015(13) C10 0.0398(15) 0.0413(18) 0.0314(14) -0.0007(12) 0.0069(11) -0.0015(13) C11 0.0399(14) 0.0389(17) 0.0331(14) -0.0027(12) 0.0076(12) 0.0009(13) C12 0.0375(14) 0.0356(16) 0.0345(14) -0.0009(12) 0.0064(12) -0.0004(13) C13 0.0360(14) 0.0362(17) 0.0344(14) 0.0000(12) 0.0055(11) -0.0018(12) C14 0.0349(14) 0.0346(16) 0.0332(14) -0.0004(12) 0.0062(11) 0.0009(12) C15 0.0366(14) 0.0380(17) 0.0304(13) -0.0008(12) 0.0060(11) 0.0002(13) C16 0.0329(14) 0.0385(17) 0.0390(15) 0.0014(13) 0.0075(12) -0.0031(13) C17 0.0438(16) 0.046(2) 0.0332(14) -0.0004(14) 0.0077(13) 0.0025(14) C18 0.0462(18) 0.068(2) 0.0503(19) 0.0047(18) 0.0188(15) 0.0001(18) C19 0.0385(17) 0.054(2) 0.068(2) 0.0134(17) 0.0101(16) 0.0057(15) C20 0.0325(13) 0.0536(17) 0.0556(15) 0.0000(15) 0.0043(11) 0.0045(13) C21 0.044(2) 0.065(3) 0.066(2) -0.011(3) 0.010(2) -0.006(3) C22 0.041(3) 0.070(3) 0.066(3) -0.012(3) 0.011(2) -0.007(3) C23 0.041(2) 0.072(3) 0.066(3) -0.009(3) 0.008(3) -0.008(2) C24 0.041(2) 0.072(3) 0.064(3) -0.007(3) 0.006(3) -0.006(2) C25 0.038(3) 0.065(3) 0.061(3) -0.004(3) 0.005(3) 0.001(2) C21' 0.045(2) 0.064(3) 0.064(2) -0.010(2) 0.010(2) -0.007(2) C22' 0.046(2) 0.069(3) 0.066(3) -0.014(2) 0.010(2) -0.008(2) C23' 0.043(2) 0.073(3) 0.066(3) -0.012(3) 0.006(3) -0.006(2) C24' 0.042(2) 0.073(3) 0.065(3) -0.008(3) -0.001(3) 0.000(2) C25' 0.035(2) 0.066(3) 0.058(3) -0.003(3) 0.005(2) 0.007(2) _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 1.434(4) . ? O2 C2 1.434(3) . ? O3 C3 1.434(3) . ? N1 C19 1.471(4) . ? N1 C4 1.477(3) . ? C1 C2 1.513(4) . ? C2 C3 1.527(3) . ? C3 C4 1.534(4) . ? C4 C5 1.545(3) . ? C5 C6 1.518(4) . ? C6 C7 1.525(4) . ? C7 C8 1.534(4) . ? C8 C9 1.520(4) . ? C9 C10 1.521(4) . ? C10 C11 1.529(3) . ? C11 C12 1.519(4) . ? C12 C13 1.519(4) . ? C13 C14 1.519(4) . ? C14 C15 1.524(3) . ? C15 C16 1.529(4) . ? C16 C17 1.516(4) . ? C17 C18 1.514(4) . ? C19 C20 1.489(4) . ? C20 C25' 1.389(8) . ? C20 C21 1.389(11) . ? C20 C21' 1.394(8) . ? C20 C25 1.419(10) . ? C21 C22 1.388(11) . ? C22 C23 1.369(11) . ? C23 C24 1.367(11) . ? C24 C25 1.382(11) . ? C21' C22' 1.402(9) . ? C22' C23' 1.354(9) . ? C23' C24' 1.375(9) . ? C24' C25' 1.367(9) . ? 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 C19 N1 C4 116.7(2) . . ? O1 C1 C2 112.6(2) . . ? O2 C2 C1 107.4(2) . . ? O2 C2 C3 112.1(2) . . ? C1 C2 C3 113.0(2) . . ? O3 C3 C2 112.0(2) . . ? O3 C3 C4 107.0(2) . . ? C2 C3 C4 113.7(2) . . ? N1 C4 C3 108.1(2) . . ? N1 C4 C5 111.2(2) . . ? C3 C4 C5 111.5(2) . . ? C6 C5 C4 115.9(2) . . ? C5 C6 C7 112.3(2) . . ? C6 C7 C8 114.2(2) . . ? C9 C8 C7 113.1(2) . . ? C8 C9 C10 113.6(2) . . ? C9 C10 C11 113.4(2) . . ? C12 C11 C10 113.9(2) . . ? C13 C12 C11 114.0(2) . . ? C12 C13 C14 114.2(2) . . ? C13 C14 C15 113.6(2) . . ? C14 C15 C16 113.8(2) . . ? C17 C16 C15 113.5(2) . . ? C18 C17 C16 114.0(3) . . ? N1 C19 C20 109.0(3) . . ? C25' C20 C21 129.8(7) . . ? C25' C20 C21' 119.9(6) . . ? C21 C20 C21' 13.0(8) . . ? C25' C20 C25 16.1(6) . . ? C21 C20 C25 115.2(7) . . ? C21' C20 C25 104.4(6) . . ? C25' C20 C19 115.3(5) . . ? C21 C20 C19 114.6(6) . . ? C21' C20 C19 124.7(5) . . ? C25 C20 C19 130.1(6) . . ? C22 C21 C20 120.9(9) . . ? C23 C22 C21 121.4(9) . . ? C24 C23 C22 120.3(9) . . ? C23 C24 C25 118.2(9) . . ? C24 C25 C20 123.7(9) . . ? C20 C21' C22' 119.3(8) . . ? C23' C22' C21' 119.1(7) . . ? C22' C23' C24' 121.9(7) . . ? C25' C24' C23' 120.0(7) . . ? C24' C25' C20 119.8(6) . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.200 _refine_diff_density_min -0.170 _refine_diff_density_rms 0.040 #===END