# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Joelle Dubois' _publ_contact_author_name 'Joelle Dubois' _publ_contact_author_email JOELLE.DUBOIS@ICSN.CNRS-GIF.FR _publ_section_title ; New asymmetric synthesis of protein farnesyltransferase inhibitors via palladium-catalyzed cross-coupling reactions of 2-iodo-imidazoles. ; # Attachment 'Compound19a.cif' data_jz363 _database_code_depnum_ccdc_archive 'CCDC 719966' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (R)-ethyl 3-((S)-4-benzyl-2-oxooxazolidine-3-carbonyl)hex-5-enoate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H23 N O5' _chemical_formula_sum 'C19 H23 N O5' _chemical_formula_weight 345.38 _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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 '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' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.361(3) _cell_length_b 10.817(4) _cell_length_c 12.310(4) _cell_angle_alpha 90.00 _cell_angle_beta 106.652(8) _cell_angle_gamma 90.00 _cell_volume 939.1(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1596 _cell_measurement_theta_min 0.41 _cell_measurement_theta_max 24.71 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.58 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.221 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 368 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.85 _exptl_absorpt_correction_T_max 0.99 _exptl_absorpt_process_details 'Scalepack (Otwinowski & Minor, 1997)' _exptl_special_details ; 8153 reflections were collected using program Collect ("Collect" Data collection software, Nonius B.V., 1998) up to resolution angle of 24.7\%. The conditions were as follows : crystal to detector distance = 31. mm. 161 images of 50 sec per frame and 2 \% per oscillation Data collection was divided into 5 set(s) of scans with the following starting angles and number of frames : Phi scan 1 len=183.0;st: theta= 4.171 phi=-1.500 omega= 160.0 kappa=0.0 Omega scan1 len=43.7;st:theta=-3.885 phi=-100.584 omega=-151.495 kappa=-167.148 Omega scan2 len=41.9;st:theta=-3.885 phi= -18.693 omega= 124.302 kappa= 119.798 Omega scan3 len=29.2;st:theta=-3.885 phi= 147.292 omega= 117.615 kappa= 130.960 Omega scan4 len=30.1;st:theta=-3.885 phi= -95.669 omega= 115.240 kappa= 134.710 In absence of significant anomalous scattering, Friedel pairs were averaged. Internal R = 0.053 Crystal absorption: use of spherical harmonics(Katayama,C.(1986) Acta Cryst.A42:19-23;Blessing,R.H.(1995)Acta Cryst.A51,33)expansion of the absorption surface as implemented in Scalepack.' ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius kappa-CCD diffractometer' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 8153 _diffrn_reflns_av_R_equivalents 0.0308 _diffrn_reflns_av_sigmaI/netI 0.0362 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.55 _diffrn_reflns_theta_max 24.59 _reflns_number_total 1648 _reflns_number_gt 1334 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)' _computing_data_reduction 'SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008); CRYSTALBUILDER (Welter, 2006)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL97 (Sheldrick, 2008)' _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. The Model has Chirality at C4: S by reference to an unchanging chiral centre in the synthetic procedure, and at C15: R. ; _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^)+(0.0506P)^2^+0.1088P] 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 0.070(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1647 _refine_ls_number_parameters 227 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0561 _refine_ls_R_factor_gt 0.0411 _refine_ls_wR_factor_ref 0.1082 _refine_ls_wR_factor_gt 0.0990 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.084 _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 O2 O 0.5079(3) 0.2982(2) -0.0660(2) 0.0737(7) Uani 1 1 d . . . O14 O 0.9274(4) 0.4933(2) 0.2112(2) 0.0772(7) Uani 1 1 d . . . O21 O 1.3000(4) 0.3535(3) 0.1780(2) 0.0877(9) Uani 1 1 d . . . O22 O 1.3924(3) 0.4591(3) 0.3395(2) 0.0817(8) Uani 1 1 d . . . O25 O 0.7225(4) 0.1669(2) 0.0351(3) 0.0844(8) Uani 1 1 d . . . N5 N 0.7380(3) 0.3784(2) 0.0733(2) 0.0564(6) Uani 1 1 d . . . C1 C 0.6640(4) 0.2707(3) 0.0175(3) 0.0646(9) Uani 1 1 d . . . C3 C 0.4608(5) 0.4278(4) -0.0593(4) 0.0754(11) Uani 1 1 d . . . H3A H 0.3608 0.4375 -0.0230 0.091 Uiso 1 1 calc R . . H3B H 0.4195 0.4644 -0.1343 0.091 Uiso 1 1 calc R . . C4 C 0.6433(4) 0.4877(3) 0.0112(3) 0.0632(9) Uani 1 1 d . . . H4 H 0.6154 0.5473 0.0642 0.076 Uiso 1 1 calc R . . C5 C 1.6212(8) 0.6205(6) 0.3775(6) 0.134(2) Uani 1 1 d . . . H5A H 1.6972 0.6729 0.3451 0.202 Uiso 1 1 calc R . . H5B H 1.7023 0.5725 0.4378 0.202 Uiso 1 1 calc R . . H5C H 1.5384 0.6704 0.4070 0.202 Uiso 1 1 calc R . . C6 C 0.7624(5) 0.5493(3) -0.0566(3) 0.0680(9) Uani 1 1 d . . . H6A H 0.6981 0.6236 -0.0918 0.082 Uiso 1 1 calc R . . H6B H 0.8831 0.5738 -0.0049 0.082 Uiso 1 1 calc R . . C7 C 0.7987(5) 0.4677(3) -0.1471(3) 0.0642(9) Uani 1 1 d . . . C8 C 0.6855(6) 0.4733(5) -0.2578(4) 0.0892(13) Uani 1 1 d . . . H8 H 0.5892 0.5318 -0.2789 0.107 Uiso 1 1 calc R . . C9 C 0.7159(8) 0.3915(7) -0.3370(5) 0.1172(18) Uani 1 1 d . . . H9 H 0.6389 0.3945 -0.4114 0.141 Uiso 1 1 calc R . . C10 C 0.8596(10) 0.3054(6) -0.3063(6) 0.126(2) Uani 1 1 d . . . H10 H 0.8781 0.2499 -0.3598 0.151 Uiso 1 1 calc R . . C11 C 0.9746(8) 0.3017(4) -0.1978(6) 0.1024(14) Uani 1 1 d . . . H11 H 1.0730 0.2446 -0.1773 0.123 Uiso 1 1 calc R . . C12 C 0.9450(5) 0.3817(4) -0.1198(3) 0.0735(9) Uani 1 1 d . . . H12 H 1.0247 0.3790 -0.0460 0.088 Uiso 1 1 calc R . . C13 C 0.8816(4) 0.3903(3) 0.1744(3) 0.0591(8) Uani 1 1 d . . . C14 C 1.5094(6) 0.5385(5) 0.2911(4) 0.1017(15) Uani 1 1 d . . . H14A H 1.5927 0.4881 0.2610 0.122 Uiso 1 1 calc R . . H14B H 1.4291 0.5866 0.2294 0.122 Uiso 1 1 calc R . . C15 C 0.9673(4) 0.2759(3) 0.2372(3) 0.0609(8) Uani 1 1 d . . . H15 H 0.9917 0.2163 0.1830 0.073 Uiso 1 1 calc R . . C16 C 0.8233(5) 0.2178(4) 0.2950(4) 0.0801(11) Uani 1 1 d . . . H16A H 0.8177 0.2692 0.3585 0.096 Uiso 1 1 calc R . . H16B H 0.6981 0.2169 0.2410 0.096 Uiso 1 1 calc R . . C17 C 0.8747(6) 0.0920(4) 0.3354(4) 0.0861(12) Uani 1 1 d . . . H17 H 0.9189 0.0403 0.2881 0.103 Uiso 1 1 calc R . . C18 C 0.8647(10) 0.0448(8) 0.4310(5) 0.150(2) Uani 1 1 d . . . H18A H 0.8214 0.0928 0.4812 0.180 Uiso 1 1 calc R . . H18B H 0.9010 -0.0367 0.4490 0.180 Uiso 1 1 calc R . . C19 C 1.1553(5) 0.3087(4) 0.3243(3) 0.0720(10) Uani 1 1 d . . . H19A H 1.1304 0.3611 0.3824 0.086 Uiso 1 1 calc R . . H19B H 1.2151 0.2336 0.3605 0.086 Uiso 1 1 calc R . . C20 C 1.2880(4) 0.3741(4) 0.2715(3) 0.0664(9) 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 O2 0.0578(13) 0.0587(14) 0.0958(18) 0.0027(13) 0.0078(12) -0.0069(12) O14 0.0788(16) 0.0521(14) 0.0975(18) -0.0087(13) 0.0202(13) -0.0059(12) O21 0.0938(18) 0.096(2) 0.0836(17) -0.0238(16) 0.0416(14) -0.0202(16) O22 0.0712(14) 0.095(2) 0.0802(17) -0.0211(16) 0.0238(13) -0.0201(15) O25 0.0854(17) 0.0413(13) 0.111(2) 0.0015(14) 0.0040(15) -0.0037(13) N5 0.0519(13) 0.0380(13) 0.0782(17) 0.0036(13) 0.0169(12) -0.0018(13) C1 0.0560(18) 0.047(2) 0.088(3) 0.0060(17) 0.0154(18) -0.0077(16) C3 0.0573(18) 0.063(2) 0.107(3) 0.011(2) 0.0239(18) 0.0040(16) C4 0.0576(17) 0.0462(17) 0.090(3) 0.0075(18) 0.0270(18) 0.0059(16) C5 0.119(4) 0.125(5) 0.154(5) -0.017(4) 0.031(4) -0.048(4) C6 0.070(2) 0.0455(17) 0.089(2) 0.0098(18) 0.0230(19) 0.0009(17) C7 0.0646(18) 0.0524(19) 0.078(2) 0.0082(17) 0.0251(17) -0.0064(17) C8 0.083(2) 0.093(3) 0.087(3) 0.012(3) 0.017(2) -0.013(3) C9 0.125(4) 0.136(5) 0.087(3) -0.019(4) 0.024(3) -0.040(4) C10 0.164(5) 0.102(4) 0.130(5) -0.040(4) 0.073(5) -0.032(4) C11 0.119(4) 0.070(3) 0.136(5) -0.010(3) 0.066(3) 0.001(3) C12 0.070(2) 0.063(2) 0.094(3) 0.006(2) 0.0333(18) 0.003(2) C13 0.0579(17) 0.0476(18) 0.078(2) -0.0004(17) 0.0293(16) -0.0040(17) C14 0.080(2) 0.120(4) 0.115(3) -0.027(3) 0.044(2) -0.033(3) C15 0.0601(17) 0.0537(18) 0.071(2) 0.0037(17) 0.0224(16) -0.0030(16) C16 0.080(2) 0.074(2) 0.093(3) 0.012(2) 0.036(2) -0.004(2) C17 0.094(3) 0.079(3) 0.090(3) 0.014(2) 0.034(2) -0.011(2) C18 0.211(6) 0.141(5) 0.112(4) 0.045(4) 0.072(4) 0.001(5) C19 0.073(2) 0.079(2) 0.065(2) 0.0054(19) 0.0194(16) -0.003(2) C20 0.0575(18) 0.073(2) 0.068(2) -0.008(2) 0.0168(16) 0.0014(19) _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 O2 C1 1.338(4) . ? O2 C3 1.453(5) . ? O14 C13 1.214(4) . ? O21 C20 1.200(4) . ? O22 C20 1.329(4) . ? O22 C14 1.459(5) . ? O25 C1 1.199(4) . ? N5 C1 1.383(4) . ? N5 C13 1.389(4) . ? N5 C4 1.471(4) . ? C3 C4 1.519(5) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C6 1.525(5) . ? C4 H4 0.9800 . ? C5 C14 1.447(7) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 C7 1.505(5) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.379(5) . ? C7 C12 1.389(5) . ? C8 C9 1.382(7) . ? C8 H8 0.9300 . ? C9 C10 1.378(9) . ? C9 H9 0.9300 . ? C10 C11 1.362(8) . ? C10 H10 0.9300 . ? C11 C12 1.356(6) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C15 1.498(5) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C19 1.530(5) . ? C15 C16 1.568(5) . ? C15 H15 0.9800 . ? C16 C17 1.460(6) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.304(6) . ? C17 H17 0.9300 . ? C18 H18A 0.9300 . ? C18 H18B 0.9300 . ? C19 C20 1.497(5) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? 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 O2 C3 109.7(3) . . ? C20 O22 C14 116.9(3) . . ? C1 N5 C13 127.8(3) . . ? C1 N5 C4 111.0(2) . . ? C13 N5 C4 121.2(3) . . ? O25 C1 O2 122.1(3) . . ? O25 C1 N5 129.0(3) . . ? O2 C1 N5 108.9(3) . . ? O2 C3 C4 104.9(3) . . ? O2 C3 H3A 110.8 . . ? C4 C3 H3A 110.8 . . ? O2 C3 H3B 110.8 . . ? C4 C3 H3B 110.8 . . ? H3A C3 H3B 108.8 . . ? N5 C4 C3 99.5(3) . . ? N5 C4 C6 112.0(3) . . ? C3 C4 C6 115.3(3) . . ? N5 C4 H4 109.9 . . ? C3 C4 H4 109.9 . . ? C6 C4 H4 109.9 . . ? C14 C5 H5A 109.5 . . ? C14 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C14 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C7 C6 C4 113.6(3) . . ? C7 C6 H6A 108.8 . . ? C4 C6 H6A 108.8 . . ? C7 C6 H6B 108.8 . . ? C4 C6 H6B 108.8 . . ? H6A C6 H6B 107.7 . . ? C8 C7 C12 118.4(4) . . ? C8 C7 C6 121.4(4) . . ? C12 C7 C6 120.2(3) . . ? C7 C8 C9 119.6(5) . . ? C7 C8 H8 120.2 . . ? C9 C8 H8 120.2 . . ? C10 C9 C8 120.4(5) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C11 C10 C9 120.1(5) . . ? C11 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? C12 C11 C10 119.6(5) . . ? C12 C11 H11 120.2 . . ? C10 C11 H11 120.2 . . ? C11 C12 C7 121.8(4) . . ? C11 C12 H12 119.1 . . ? C7 C12 H12 119.1 . . ? O14 C13 N5 118.5(3) . . ? O14 C13 C15 122.3(3) . . ? N5 C13 C15 119.1(3) . . ? C5 C14 O22 109.8(4) . . ? C5 C14 H14A 109.7 . . ? O22 C14 H14A 109.7 . . ? C5 C14 H14B 109.7 . . ? O22 C14 H14B 109.7 . . ? H14A C14 H14B 108.2 . . ? C13 C15 C19 109.4(3) . . ? C13 C15 C16 109.0(3) . . ? C19 C15 C16 111.6(3) . . ? C13 C15 H15 108.9 . . ? C19 C15 H15 108.9 . . ? C16 C15 H15 108.9 . . ? C17 C16 C15 112.7(3) . . ? C17 C16 H16A 109.1 . . ? C15 C16 H16A 109.1 . . ? C17 C16 H16B 109.1 . . ? C15 C16 H16B 109.1 . . ? H16A C16 H16B 107.8 . . ? C18 C17 C16 126.6(6) . . ? C18 C17 H17 116.7 . . ? C16 C17 H17 116.7 . . ? C17 C18 H18A 120.0 . . ? C17 C18 H18B 120.0 . . ? H18A C18 H18B 120.0 . . ? C20 C19 C15 112.2(3) . . ? C20 C19 H19A 109.2 . . ? C15 C19 H19A 109.2 . . ? C20 C19 H19B 109.2 . . ? C15 C19 H19B 109.2 . . ? H19A C19 H19B 107.9 . . ? O21 C20 O22 122.9(3) . . ? O21 C20 C19 124.4(3) . . ? O22 C20 C19 112.6(3) . . ? 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 C3 O2 C1 O25 174.0(4) . . . . ? C3 O2 C1 N5 -6.6(4) . . . . ? C13 N5 C1 O25 -11.0(6) . . . . ? C4 N5 C1 O25 169.2(4) . . . . ? C13 N5 C1 O2 169.7(3) . . . . ? C4 N5 C1 O2 -10.2(4) . . . . ? C1 O2 C3 C4 19.8(4) . . . . ? C1 N5 C4 C3 21.0(3) . . . . ? C13 N5 C4 C3 -158.9(3) . . . . ? C1 N5 C4 C6 -101.2(3) . . . . ? C13 N5 C4 C6 78.9(4) . . . . ? O2 C3 C4 N5 -23.5(4) . . . . ? O2 C3 C4 C6 96.4(4) . . . . ? N5 C4 C6 C7 62.3(4) . . . . ? C3 C4 C6 C7 -50.4(4) . . . . ? C4 C6 C7 C8 95.2(4) . . . . ? C4 C6 C7 C12 -82.8(4) . . . . ? C12 C7 C8 C9 2.1(6) . . . . ? C6 C7 C8 C9 -175.9(4) . . . . ? C7 C8 C9 C10 -0.7(7) . . . . ? C8 C9 C10 C11 -0.9(9) . . . . ? C9 C10 C11 C12 1.1(8) . . . . ? C10 C11 C12 C7 0.5(7) . . . . ? C8 C7 C12 C11 -2.1(5) . . . . ? C6 C7 C12 C11 176.0(4) . . . . ? C1 N5 C13 O14 -179.5(3) . . . . ? C4 N5 C13 O14 0.3(4) . . . . ? C1 N5 C13 C15 -2.7(5) . . . . ? C4 N5 C13 C15 177.2(3) . . . . ? C20 O22 C14 C5 -176.8(4) . . . . ? O14 C13 C15 C19 -19.6(4) . . . . ? N5 C13 C15 C19 163.7(3) . . . . ? O14 C13 C15 C16 102.7(4) . . . . ? N5 C13 C15 C16 -74.0(4) . . . . ? C13 C15 C16 C17 166.5(3) . . . . ? C19 C15 C16 C17 -72.5(5) . . . . ? C15 C16 C17 C18 138.7(5) . . . . ? C13 C15 C19 C20 -54.4(4) . . . . ? C16 C15 C19 C20 -175.2(3) . . . . ? C14 O22 C20 O21 7.0(5) . . . . ? C14 O22 C20 C19 -172.7(4) . . . . ? C15 C19 C20 O21 -34.7(6) . . . . ? C15 C19 C20 O22 145.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 24.59 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.162 _refine_diff_density_min -0.126 _refine_diff_density_rms 0.027