# 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 'Burgess, Kevin' 'Fedoseyenko, Dmytro' 'Raghuraman, Arjun' 'Ko, Eunhwa' _publ_contact_author_email burgess@mail.chem.tamu.edu _publ_section_title ; Omegatides: Constrained Analogs of Peptide Primary Sequence ; # Attachment '- compound 1c.cif' data_kb88 _database_code_depnum_ccdc_archive 'CCDC 854831' #TrackingRef '- compound 1c.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H18 N2 O3' _chemical_formula_weight 226.27 _chemical_absolute_configuration rm 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 Tetragonal _symmetry_space_group_name_H-M I4(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y+1/2, x, z+3/4' 'y+1/2, -x, z+3/4' '-x, -y, z' 'x+1/2, y+1/2, z+1/2' '-y+1, x+1/2, z+5/4' 'y+1, -x+1/2, z+5/4' '-x+1/2, -y+1/2, z+1/2' _cell_length_a 19.2441(10) _cell_length_b 19.2441(10) _cell_length_c 14.2264(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5268.5(6) _cell_formula_units_Z 16 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 9860 _cell_measurement_theta_min 2.76 _cell_measurement_theta_max 22.01 _exptl_crystal_description 'plate ' _exptl_crystal_colour 'colorless ' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.141 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1952 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9754 _exptl_absorpt_correction_T_max 0.9917 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(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 'MWPC area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 61500 _diffrn_reflns_av_R_equivalents 0.0584 _diffrn_reflns_av_sigmaI/netI 0.0352 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.50 _diffrn_reflns_theta_max 29.00 _reflns_number_total 6975 _reflns_number_gt 5420 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEXII' _computing_cell_refinement 'Bruker APEXII' _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^)+(0.0467P)^2^+1.3463P] 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 -0.3(7) _refine_ls_number_reflns 6975 _refine_ls_number_parameters 289 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0613 _refine_ls_R_factor_gt 0.0412 _refine_ls_wR_factor_ref 0.1014 _refine_ls_wR_factor_gt 0.0915 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.013 _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 O1A O 0.02595(6) 0.27654(6) 0.24723(8) 0.0328(3) Uani 1 1 d . . . O2A O 0.32146(7) 0.35666(6) 0.27295(9) 0.0443(3) Uani 1 1 d . . . O3A O 0.33678(6) 0.42677(6) 0.14669(8) 0.0371(3) Uani 1 1 d . . . N1A N 0.05794(8) 0.33183(8) 0.38343(10) 0.0394(4) Uani 1 1 d . . . H1AA H 0.0249 0.3146 0.4192 0.047 Uiso 1 1 calc R . . N2A N 0.20586(7) 0.43685(7) 0.32906(10) 0.0331(3) Uani 1 1 d . . . H2A H 0.2278 0.4485 0.3870 0.050 Uiso 1 1 d R . . C1A C 0.15200(8) 0.39221(8) 0.32718(12) 0.0295(3) Uani 1 1 d . . . C2A C 0.12304(8) 0.35700(8) 0.25480(12) 0.0310(3) Uani 1 1 d . . . H2AA H 0.1383 0.3580 0.1913 0.037 Uiso 1 1 calc R . . C3A C 0.06507(8) 0.31770(9) 0.29082(12) 0.0308(3) Uani 1 1 d . . . C4A C 0.11135(10) 0.37887(10) 0.41648(13) 0.0395(4) Uani 1 1 d . . . H4AA H 0.0892 0.4232 0.4377 0.047 Uiso 1 1 calc R . . C5A C 0.15333(13) 0.34869(13) 0.49642(15) 0.0639(7) Uani 1 1 d . . . H5AA H 0.1232 0.3419 0.5512 0.096 Uiso 1 1 calc R . . H5AB H 0.1911 0.3807 0.5127 0.096 Uiso 1 1 calc R . . H5AC H 0.1729 0.3039 0.4772 0.096 Uiso 1 1 calc R . . C6A C 0.24414(8) 0.45335(8) 0.24485(12) 0.0321(3) Uani 1 1 d . . . H6AA H 0.2621 0.5014 0.2502 0.038 Uiso 1 1 calc R . . H6AB H 0.2118 0.4521 0.1907 0.038 Uiso 1 1 calc R . . C7A C 0.30459(9) 0.40511(9) 0.22469(12) 0.0324(4) Uani 1 1 d . . . C8A C 0.39819(10) 0.38994(10) 0.10932(15) 0.0426(4) Uani 1 1 d . . . C9A C 0.45750(11) 0.39455(12) 0.17871(17) 0.0549(5) Uani 1 1 d . . . H9AA H 0.4463 0.3671 0.2347 0.082 Uiso 1 1 calc R . . H9AB H 0.4647 0.4432 0.1967 0.082 Uiso 1 1 calc R . . H9AC H 0.4999 0.3763 0.1497 0.082 Uiso 1 1 calc R . . C10A C 0.41567(12) 0.43175(14) 0.02172(18) 0.0665(7) Uani 1 1 d . . . H10A H 0.3772 0.4285 -0.0232 0.100 Uiso 1 1 calc R . . H10B H 0.4581 0.4132 -0.0070 0.100 Uiso 1 1 calc R . . H10C H 0.4230 0.4805 0.0390 0.100 Uiso 1 1 calc R . . C11A C 0.37887(13) 0.31664(13) 0.0855(2) 0.0678(7) Uani 1 1 d . . . H11A H 0.3405 0.3168 0.0402 0.102 Uiso 1 1 calc R . . H11B H 0.3644 0.2923 0.1428 0.102 Uiso 1 1 calc R . . H11C H 0.4191 0.2929 0.0581 0.102 Uiso 1 1 calc R . . O1B O 0.46527(6) 0.75372(6) -0.00225(8) 0.0344(3) Uani 1 1 d . . . O2B O 0.18431(7) 0.64121(6) -0.02317(9) 0.0415(3) Uani 1 1 d . . . O3B O 0.18359(6) 0.58695(6) 0.11787(8) 0.0361(3) Uani 1 1 d . . . N1B N 0.43420(8) 0.69609(8) -0.13695(10) 0.0378(3) Uani 1 1 d . . . H1BA H 0.4623 0.7186 -0.1751 0.045 Uiso 1 1 calc R . . N2B N 0.30594(7) 0.57030(7) -0.07313(9) 0.0286(3) Uani 1 1 d . . . H2B H 0.2840 0.5552 -0.1310 0.043 Uiso 1 1 d R . . C1B C 0.35267(8) 0.62228(8) -0.07507(11) 0.0274(3) Uani 1 1 d . . . C2B C 0.37840(8) 0.66211(8) -0.00437(11) 0.0293(3) Uani 1 1 d . . . H2BA H 0.3650 0.6599 0.0599 0.035 Uiso 1 1 calc R . . C3B C 0.42965(8) 0.70833(8) -0.04413(11) 0.0295(3) Uani 1 1 d . . . C4B C 0.38731(8) 0.64153(9) -0.16675(12) 0.0312(4) Uani 1 1 d . . . H4BA H 0.3520 0.6610 -0.2111 0.037 Uiso 1 1 calc R . . C5B C 0.42512(10) 0.58128(10) -0.21324(13) 0.0439(5) Uani 1 1 d . . . H5BA H 0.4461 0.5971 -0.2722 0.066 Uiso 1 1 calc R . . H5BB H 0.3920 0.5438 -0.2264 0.066 Uiso 1 1 calc R . . H5BC H 0.4616 0.5641 -0.1711 0.066 Uiso 1 1 calc R . . C6B C 0.27007(8) 0.55355(8) 0.01279(12) 0.0307(3) Uani 1 1 d . . . H6BA H 0.3031 0.5573 0.0659 0.037 Uiso 1 1 calc R . . H6BB H 0.2540 0.5047 0.0097 0.037 Uiso 1 1 calc R . . C7B C 0.20806(8) 0.60033(8) 0.03177(11) 0.0299(3) Uani 1 1 d . . . C8B C 0.12198(9) 0.62468(9) 0.15491(12) 0.0354(4) Uani 1 1 d . . . C9B C 0.05866(9) 0.60512(11) 0.09667(15) 0.0446(4) Uani 1 1 d . . . H9BA H 0.0635 0.6242 0.0331 0.067 Uiso 1 1 calc R . . H9BB H 0.0168 0.6242 0.1261 0.067 Uiso 1 1 calc R . . H9BC H 0.0549 0.5544 0.0932 0.067 Uiso 1 1 calc R . . C10B C 0.13624(11) 0.70173(11) 0.15623(17) 0.0523(5) Uani 1 1 d . . . H10D H 0.1777 0.7110 0.1943 0.078 Uiso 1 1 calc R . . H10E H 0.0963 0.7261 0.1834 0.078 Uiso 1 1 calc R . . H10F H 0.1440 0.7182 0.0919 0.078 Uiso 1 1 calc R . . C11B C 0.11492(11) 0.59590(13) 0.25347(15) 0.0575(6) Uani 1 1 d . . . H11D H 0.1559 0.6087 0.2905 0.086 Uiso 1 1 calc R . . H11E H 0.1111 0.5452 0.2506 0.086 Uiso 1 1 calc R . . H11F H 0.0732 0.6152 0.2831 0.086 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 O1A 0.0291(5) 0.0402(6) 0.0292(6) -0.0046(5) -0.0001(5) -0.0045(5) O2A 0.0556(8) 0.0382(7) 0.0391(8) 0.0106(6) 0.0004(6) 0.0074(6) O3A 0.0356(6) 0.0428(7) 0.0330(7) 0.0076(5) 0.0060(5) 0.0076(5) N1A 0.0381(8) 0.0500(9) 0.0300(8) -0.0086(7) 0.0093(6) -0.0162(7) N2A 0.0338(7) 0.0372(8) 0.0283(7) 0.0033(6) 0.0011(6) -0.0087(6) C1A 0.0297(8) 0.0315(8) 0.0274(8) 0.0031(6) 0.0007(6) 0.0009(6) C2A 0.0294(8) 0.0387(9) 0.0248(8) 0.0022(7) 0.0024(6) -0.0027(7) C3A 0.0285(8) 0.0363(8) 0.0277(8) -0.0001(7) 0.0004(6) 0.0029(7) C4A 0.0453(10) 0.0415(9) 0.0318(10) -0.0047(8) 0.0063(8) -0.0142(8) C5A 0.0762(15) 0.0769(15) 0.0386(11) 0.0191(11) -0.0129(11) -0.0426(13) C6A 0.0325(8) 0.0349(8) 0.0288(9) 0.0075(7) 0.0021(7) -0.0032(7) C7A 0.0354(8) 0.0334(8) 0.0283(9) 0.0028(7) -0.0039(7) -0.0038(7) C8A 0.0372(10) 0.0457(11) 0.0450(11) -0.0007(9) 0.0039(8) 0.0103(8) C9A 0.0421(11) 0.0560(12) 0.0668(15) 0.0024(11) -0.0030(10) 0.0087(9) C10A 0.0540(13) 0.0888(18) 0.0568(14) 0.0185(13) 0.0227(11) 0.0248(12) C11A 0.0598(14) 0.0631(14) 0.0805(18) -0.0275(14) 0.0121(13) 0.0023(11) O1B 0.0378(6) 0.0359(6) 0.0295(6) -0.0067(5) 0.0034(5) -0.0086(5) O2B 0.0486(7) 0.0447(7) 0.0311(7) 0.0070(6) 0.0024(6) 0.0124(6) O3B 0.0334(6) 0.0458(7) 0.0291(6) 0.0084(5) 0.0067(5) 0.0089(5) N1B 0.0449(8) 0.0438(8) 0.0248(7) -0.0020(6) 0.0043(6) -0.0165(7) N2B 0.0276(6) 0.0355(7) 0.0227(7) -0.0006(6) 0.0003(5) -0.0041(5) C1B 0.0249(7) 0.0306(8) 0.0267(8) 0.0004(6) -0.0004(6) 0.0029(6) C2B 0.0312(8) 0.0345(8) 0.0222(8) -0.0019(7) 0.0028(6) -0.0028(6) C3B 0.0308(8) 0.0309(8) 0.0268(8) -0.0024(6) 0.0005(6) 0.0001(6) C4B 0.0317(8) 0.0388(9) 0.0232(8) -0.0022(7) -0.0006(6) -0.0072(7) C5B 0.0346(9) 0.0565(11) 0.0407(10) -0.0188(9) 0.0095(8) -0.0091(8) C6B 0.0289(8) 0.0341(8) 0.0290(9) 0.0040(7) 0.0026(6) -0.0001(6) C7B 0.0325(8) 0.0315(8) 0.0258(8) 0.0011(6) -0.0019(7) -0.0012(6) C8B 0.0309(8) 0.0438(9) 0.0314(9) 0.0016(7) 0.0039(7) 0.0079(7) C9B 0.0343(9) 0.0507(11) 0.0488(11) -0.0085(9) 0.0014(9) 0.0073(8) C10B 0.0515(12) 0.0484(11) 0.0570(13) -0.0172(10) 0.0139(10) -0.0029(9) C11B 0.0450(11) 0.0891(17) 0.0385(11) 0.0157(11) 0.0147(9) 0.0217(11) _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 O1A C3A 1.256(2) . ? O2A C7A 1.203(2) . ? O3A C7A 1.337(2) . ? O3A C8A 1.477(2) . ? N1A C3A 1.352(2) . ? N1A C4A 1.448(2) . ? N1A H1AA 0.8800 . ? N2A C1A 1.346(2) . ? N2A C6A 1.442(2) . ? N2A H2A 0.9523 . ? C1A C2A 1.353(2) . ? C1A C4A 1.514(2) . ? C2A C3A 1.442(2) . ? C2A H2AA 0.9500 . ? C4A C5A 1.511(3) . ? C4A H4AA 1.0000 . ? C5A H5AA 0.9800 . ? C5A H5AB 0.9800 . ? C5A H5AC 0.9800 . ? C6A C7A 1.516(2) . ? C6A H6AA 0.9900 . ? C6A H6AB 0.9900 . ? C8A C11A 1.498(3) . ? C8A C9A 1.512(3) . ? C8A C10A 1.521(3) . ? C9A H9AA 0.9800 . ? C9A H9AB 0.9800 . ? C9A H9AC 0.9800 . ? C10A H10A 0.9800 . ? C10A H10B 0.9800 . ? C10A H10C 0.9800 . ? C11A H11A 0.9800 . ? C11A H11B 0.9800 . ? C11A H11C 0.9800 . ? O1B C3B 1.260(2) . ? O2B C7B 1.1995(19) . ? O3B C7B 1.337(2) . ? O3B C8B 1.487(2) . ? N1B C3B 1.344(2) . ? N1B C4B 1.448(2) . ? N1B H1BA 0.8800 . ? N2B C1B 1.345(2) . ? N2B C6B 1.440(2) . ? N2B H2B 0.9695 . ? C1B C2B 1.358(2) . ? C1B C4B 1.511(2) . ? C2B C3B 1.444(2) . ? C2B H2BA 0.9500 . ? C4B C5B 1.520(2) . ? C4B H4BA 1.0000 . ? C5B H5BA 0.9800 . ? C5B H5BB 0.9800 . ? C5B H5BC 0.9800 . ? C6B C7B 1.519(2) . ? C6B H6BA 0.9900 . ? C6B H6BB 0.9900 . ? C8B C10B 1.508(3) . ? C8B C11B 1.514(3) . ? C8B C9B 1.521(3) . ? C9B H9BA 0.9800 . ? C9B H9BB 0.9800 . ? C9B H9BC 0.9800 . ? C10B H10D 0.9800 . ? C10B H10E 0.9800 . ? C10B H10F 0.9800 . ? C11B H11D 0.9800 . ? C11B H11E 0.9800 . ? C11B H11F 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 C7A O3A C8A 121.32(14) . . ? C3A N1A C4A 111.72(15) . . ? C3A N1A H1AA 124.1 . . ? C4A N1A H1AA 124.1 . . ? C1A N2A C6A 121.16(14) . . ? C1A N2A H2A 120.6 . . ? C6A N2A H2A 116.1 . . ? N2A C1A C2A 130.68(15) . . ? N2A C1A C4A 119.29(15) . . ? C2A C1A C4A 109.93(14) . . ? C1A C2A C3A 108.12(15) . . ? C1A C2A H2AA 125.9 . . ? C3A C2A H2AA 125.9 . . ? O1A C3A N1A 123.15(16) . . ? O1A C3A C2A 128.24(15) . . ? N1A C3A C2A 108.62(15) . . ? N1A C4A C5A 112.56(16) . . ? N1A C4A C1A 101.55(14) . . ? C5A C4A C1A 114.86(16) . . ? N1A C4A H4AA 109.2 . . ? C5A C4A H4AA 109.2 . . ? C1A C4A H4AA 109.2 . . ? C4A C5A H5AA 109.5 . . ? C4A C5A H5AB 109.5 . . ? H5AA C5A H5AB 109.5 . . ? C4A C5A H5AC 109.5 . . ? H5AA C5A H5AC 109.5 . . ? H5AB C5A H5AC 109.5 . . ? N2A C6A C7A 114.49(14) . . ? N2A C6A H6AA 108.6 . . ? C7A C6A H6AA 108.6 . . ? N2A C6A H6AB 108.6 . . ? C7A C6A H6AB 108.6 . . ? H6AA C6A H6AB 107.6 . . ? O2A C7A O3A 126.18(16) . . ? O2A C7A C6A 125.03(16) . . ? O3A C7A C6A 108.76(14) . . ? O3A C8A C11A 109.55(16) . . ? O3A C8A C9A 109.93(17) . . ? C11A C8A C9A 112.97(19) . . ? O3A C8A C10A 102.60(15) . . ? C11A C8A C10A 111.6(2) . . ? C9A C8A C10A 109.69(18) . . ? C8A C9A H9AA 109.5 . . ? C8A C9A H9AB 109.5 . . ? H9AA C9A H9AB 109.5 . . ? C8A C9A H9AC 109.5 . . ? H9AA C9A H9AC 109.5 . . ? H9AB C9A H9AC 109.5 . . ? C8A C10A H10A 109.5 . . ? C8A C10A H10B 109.5 . . ? H10A C10A H10B 109.5 . . ? C8A C10A H10C 109.5 . . ? H10A C10A H10C 109.5 . . ? H10B C10A H10C 109.5 . . ? C8A C11A H11A 109.5 . . ? C8A C11A H11B 109.5 . . ? H11A C11A H11B 109.5 . . ? C8A C11A H11C 109.5 . . ? H11A C11A H11C 109.5 . . ? H11B C11A H11C 109.5 . . ? C7B O3B C8B 120.76(13) . . ? C3B N1B C4B 111.97(14) . . ? C3B N1B H1BA 124.0 . . ? C4B N1B H1BA 124.0 . . ? C1B N2B C6B 120.28(13) . . ? C1B N2B H2B 119.7 . . ? C6B N2B H2B 116.4 . . ? N2B C1B C2B 130.41(15) . . ? N2B C1B C4B 119.67(14) . . ? C2B C1B C4B 109.87(13) . . ? C1B C2B C3B 107.86(14) . . ? C1B C2B H2BA 126.1 . . ? C3B C2B H2BA 126.1 . . ? O1B C3B N1B 123.40(15) . . ? O1B C3B C2B 127.85(15) . . ? N1B C3B C2B 108.75(14) . . ? N1B C4B C1B 101.54(13) . . ? N1B C4B C5B 112.47(14) . . ? C1B C4B C5B 113.56(15) . . ? N1B C4B H4BA 109.7 . . ? C1B C4B H4BA 109.7 . . ? C5B C4B H4BA 109.7 . . ? C4B C5B H5BA 109.5 . . ? C4B C5B H5BB 109.5 . . ? H5BA C5B H5BB 109.5 . . ? C4B C5B H5BC 109.5 . . ? H5BA C5B H5BC 109.5 . . ? H5BB C5B H5BC 109.5 . . ? N2B C6B C7B 113.25(13) . . ? N2B C6B H6BA 108.9 . . ? C7B C6B H6BA 108.9 . . ? N2B C6B H6BB 108.9 . . ? C7B C6B H6BB 108.9 . . ? H6BA C6B H6BB 107.7 . . ? O2B C7B O3B 126.08(15) . . ? O2B C7B C6B 124.90(15) . . ? O3B C7B C6B 109.00(13) . . ? O3B C8B C10B 109.85(14) . . ? O3B C8B C11B 102.77(14) . . ? C10B C8B C11B 111.38(18) . . ? O3B C8B C9B 108.96(14) . . ? C10B C8B C9B 113.32(16) . . ? C11B C8B C9B 110.01(17) . . ? C8B C9B H9BA 109.5 . . ? C8B C9B H9BB 109.5 . . ? H9BA C9B H9BB 109.5 . . ? C8B C9B H9BC 109.5 . . ? H9BA C9B H9BC 109.5 . . ? H9BB C9B H9BC 109.5 . . ? C8B C10B H10D 109.5 . . ? C8B C10B H10E 109.5 . . ? H10D C10B H10E 109.5 . . ? C8B C10B H10F 109.5 . . ? H10D C10B H10F 109.5 . . ? H10E C10B H10F 109.5 . . ? C8B C11B H11D 109.5 . . ? C8B C11B H11E 109.5 . . ? H11D C11B H11E 109.5 . . ? C8B C11B H11F 109.5 . . ? H11D C11B H11F 109.5 . . ? H11E C11B H11F 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 C6A N2A C1A C2A -1.2(3) . . . . ? C6A N2A C1A C4A -177.33(15) . . . . ? N2A C1A C2A C3A -178.30(17) . . . . ? C4A C1A C2A C3A -1.91(19) . . . . ? C4A N1A C3A O1A 177.86(16) . . . . ? C4A N1A C3A C2A -2.1(2) . . . . ? C1A C2A C3A O1A -177.46(16) . . . . ? C1A C2A C3A N1A 2.51(19) . . . . ? C3A N1A C4A C5A -122.40(19) . . . . ? C3A N1A C4A C1A 0.94(19) . . . . ? N2A C1A C4A N1A 177.53(15) . . . . ? C2A C1A C4A N1A 0.67(19) . . . . ? N2A C1A C4A C5A -60.7(2) . . . . ? C2A C1A C4A C5A 122.42(17) . . . . ? C1A N2A C6A C7A -88.66(19) . . . . ? C8A O3A C7A O2A 1.8(3) . . . . ? C8A O3A C7A C6A 179.85(15) . . . . ? N2A C6A C7A O2A -0.3(3) . . . . ? N2A C6A C7A O3A -178.43(13) . . . . ? C7A O3A C8A C11A 60.6(2) . . . . ? C7A O3A C8A C9A -64.1(2) . . . . ? C7A O3A C8A C10A 179.28(17) . . . . ? C6B N2B C1B C2B 5.8(3) . . . . ? C6B N2B C1B C4B -177.04(14) . . . . ? N2B C1B C2B C3B 177.40(15) . . . . ? C4B C1B C2B C3B 0.06(18) . . . . ? C4B N1B C3B O1B -179.70(15) . . . . ? C4B N1B C3B C2B -0.1(2) . . . . ? C1B C2B C3B O1B 179.60(16) . . . . ? C1B C2B C3B N1B 0.02(19) . . . . ? C3B N1B C4B C1B 0.12(18) . . . . ? C3B N1B C4B C5B -121.61(17) . . . . ? N2B C1B C4B N1B -177.78(13) . . . . ? C2B C1B C4B N1B -0.11(18) . . . . ? N2B C1B C4B C5B -56.8(2) . . . . ? C2B C1B C4B C5B 120.87(16) . . . . ? C1B N2B C6B C7B 81.96(18) . . . . ? C8B O3B C7B O2B -0.9(3) . . . . ? C8B O3B C7B C6B -179.18(13) . . . . ? N2B C6B C7B O2B 9.6(2) . . . . ? N2B C6B C7B O3B -172.19(13) . . . . ? C7B O3B C8B C10B -59.1(2) . . . . ? C7B O3B C8B C11B -177.69(17) . . . . ? C7B O3B C8B C9B 65.6(2) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 29.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.211 _refine_diff_density_min -0.164 _refine_diff_density_rms 0.033 # Attachment '- compound 3a.cif' data_kb1 _database_code_depnum_ccdc_archive 'CCDC 854832' #TrackingRef '- compound 3a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H28 N2 O3' _chemical_formula_weight 308.41 _chemical_absolute_configuration ab 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 Triclinic _symmetry_space_group_name_H-M P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 5.6765(4) _cell_length_b 10.5601(9) _cell_length_c 15.2326(11) _cell_angle_alpha 80.631(7) _cell_angle_beta 85.199(5) _cell_angle_gamma 75.014(5) _cell_volume 869.46(11) _cell_formula_units_Z 2 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 4640 _cell_measurement_theta_min 2.94 _cell_measurement_theta_max 61.40 _exptl_crystal_description block _exptl_crystal_colour 'colorless ' _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.178 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 336 _exptl_absorpt_coefficient_mu 0.645 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9383 _exptl_absorpt_correction_T_max 0.9936 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'MWPC area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 15073 _diffrn_reflns_av_R_equivalents 0.0395 _diffrn_reflns_av_sigmaI/netI 0.0404 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.94 _diffrn_reflns_theta_max 59.93 _reflns_number_total 4739 _reflns_number_gt 4263 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker FRAMBO' _computing_cell_refinement 'Bruker FRAMBO' _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^)+(0.0609P)^2^+0.0000P] 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_abs_structure_details ; Flack H D (1983), Acta Cryst. A39, 876-881 hooft parameter : -0.05(11) parson Q parameter : -0.11(09) ; _refine_ls_abs_structure_Flack 0.05(11) _refine_ls_number_reflns 4739 _refine_ls_number_parameters 397 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0424 _refine_ls_R_factor_gt 0.0372 _refine_ls_wR_factor_ref 0.0923 _refine_ls_wR_factor_gt 0.0902 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.001 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 O1A O 0.6146(4) 0.75764(18) 1.09801(12) 0.0365(5) Uani 1 1 d . . . N1A N 0.5046(4) 0.9351(2) 0.98711(13) 0.0254(5) Uani 1 1 d . . . H1AA H 0.5740 0.9877 1.0068 0.031 Uiso 1 1 calc R . . C1A C 0.7214(4) 0.7030(2) 0.83909(16) 0.0217(5) Uani 1 1 d . . . O2A O 0.8448(3) 0.72811(16) 0.89420(11) 0.0264(4) Uani 1 1 d . . . N2A N 0.4826(4) 0.76763(19) 0.82374(12) 0.0211(5) Uani 1 1 d . . . C2A C 0.7981(5) 0.5990(2) 0.78213(16) 0.0238(5) Uani 1 1 d . . . H2AA H 0.9551 0.5460 0.7752 0.029 Uiso 1 1 calc R . . O3A O 0.5565(3) 0.51573(16) 0.68788(11) 0.0256(4) Uani 1 1 d . . . C3A C 0.6002(5) 0.5945(2) 0.74201(16) 0.0240(6) Uani 1 1 d . . . C4A C 0.3810(4) 0.7003(2) 0.76532(15) 0.0218(5) Uani 1 1 d . . . H4AA H 0.2636 0.6570 0.8007 0.026 Uiso 1 1 calc R . . C5A C 0.3210(5) 0.8391(2) 0.88910(15) 0.0215(5) Uani 1 1 d . . . H5AA H 0.1527 0.8588 0.8704 0.026 Uiso 1 1 calc R . . C6A C 0.3353(5) 0.7604(3) 0.98281(16) 0.0270(6) Uani 1 1 d . . . H6AA H 0.1750 0.7742 1.0128 0.032 Uiso 1 1 calc R . . H6AB H 0.3994 0.6665 0.9805 0.032 Uiso 1 1 calc R . . C7A C 0.5047(5) 0.8122(2) 1.03073(17) 0.0261(6) Uani 1 1 d . . . C8A C 0.3766(5) 0.9706(2) 0.90377(16) 0.0239(6) Uani 1 1 d . . . H8AA H 0.2207 1.0339 0.9140 0.029 Uiso 1 1 calc R . . C9A C 0.5180(5) 1.0360(3) 0.82927(18) 0.0320(6) Uani 1 1 d . . . H9AA H 0.5412 1.1160 0.8454 0.048 Uiso 1 1 calc R . . H9AB H 0.4285 1.0568 0.7759 0.048 Uiso 1 1 calc R . . H9AC H 0.6740 0.9767 0.8192 0.048 Uiso 1 1 calc R . . C10A C 0.7430(5) 0.3961(3) 0.66814(18) 0.0305(6) Uani 1 1 d . . . C11A C 0.9366(5) 0.4381(3) 0.60348(19) 0.0377(7) Uani 1 1 d . . . H11A H 0.8609 0.4910 0.5511 0.057 Uiso 1 1 calc R . . H11B H 1.0527 0.3608 0.5873 0.057 Uiso 1 1 calc R . . H11C H 1.0187 0.4891 0.6312 0.057 Uiso 1 1 calc R . . C12A C 0.5956(5) 0.3247(3) 0.6241(2) 0.0371(7) Uani 1 1 d . . . H12A H 0.5318 0.3788 0.5702 0.056 Uiso 1 1 calc R . . H12B H 0.4630 0.3080 0.6639 0.056 Uiso 1 1 calc R . . H12C H 0.6986 0.2421 0.6104 0.056 Uiso 1 1 calc R . . C13A C 0.8465(5) 0.3111(3) 0.75367(18) 0.0342(6) Uani 1 1 d . . . H13A H 0.7162 0.2873 0.7916 0.051 Uiso 1 1 calc R . . H13B H 0.9267 0.3602 0.7838 0.051 Uiso 1 1 calc R . . H13C H 0.9617 0.2323 0.7395 0.051 Uiso 1 1 calc R . . C14A C 0.2492(5) 0.7936(3) 0.68692(16) 0.0289(6) Uani 1 1 d . . . H14A H 0.2006 0.7402 0.6490 0.035 Uiso 1 1 calc R . . H14C H 0.1011 0.8492 0.7102 0.035 Uiso 1 1 calc R . . C15A C 0.3909(6) 0.8833(3) 0.62906(17) 0.0367(7) Uani 1 1 d . . . H15A H 0.4810 0.9166 0.6686 0.044 Uiso 1 1 calc R . . C16A C 0.5747(7) 0.8130(3) 0.5631(2) 0.0496(8) Uani 1 1 d . . . H16A H 0.6571 0.8746 0.5288 0.074 Uiso 1 1 calc R . . H16B H 0.4910 0.7784 0.5240 0.074 Uiso 1 1 calc R . . H16C H 0.6918 0.7415 0.5949 0.074 Uiso 1 1 calc R . . C17A C 0.2173(10) 1.0016(4) 0.5789(3) 0.1012(19) Uani 1 1 d . . . H17A H 0.3090 1.0570 0.5427 0.152 Uiso 1 1 calc R . . H17B H 0.1113 1.0513 0.6206 0.152 Uiso 1 1 calc R . . H17C H 0.1214 0.9715 0.5415 0.152 Uiso 1 1 calc R . . O1B O 1.2865(3) 1.44377(18) 0.88677(12) 0.0347(4) Uani 1 1 d . . . N1B N 1.0505(4) 1.4752(2) 1.01557(14) 0.0287(5) Uani 1 1 d . . . H1BA H 1.0204 1.5602 1.0089 0.034 Uiso 1 1 calc R . . C1B C 0.9146(5) 1.0758(2) 1.09747(16) 0.0234(6) Uani 1 1 d . . . O2B O 0.8140(3) 1.11221(16) 1.02552(11) 0.0277(4) Uani 1 1 d . . . N2B N 1.0463(4) 1.1447(2) 1.13468(13) 0.0230(5) Uani 1 1 d . . . C2B C 0.9179(5) 0.9515(2) 1.15753(16) 0.0235(6) Uani 1 1 d . . . H2BA H 0.8371 0.8883 1.1496 0.028 Uiso 1 1 calc R . . O3B O 1.1269(3) 0.85606(16) 1.29750(11) 0.0280(4) Uani 1 1 d . . . C3B C 1.0563(5) 0.9451(2) 1.22515(16) 0.0256(6) Uani 1 1 d . . . C4B C 1.1606(5) 1.0651(2) 1.21542(17) 0.0260(6) Uani 1 1 d . . . H4BA H 1.3365 1.0362 1.2020 0.031 Uiso 1 1 calc R . . C5B C 1.1320(5) 1.2588(2) 1.09053(16) 0.0235(5) Uani 1 1 d . . . H5BA H 1.2736 1.2600 1.1228 0.028 Uiso 1 1 calc R . . C6B C 1.2185(5) 1.2577(2) 0.99362(17) 0.0256(6) Uani 1 1 d . . . H6BA H 1.3868 1.2072 0.9885 0.031 Uiso 1 1 calc R . . H6BB H 1.1175 1.2200 0.9623 0.031 Uiso 1 1 calc R . . C7B C 1.1937(5) 1.4019(2) 0.95714(17) 0.0263(6) Uani 1 1 d . . . C8B C 0.9509(5) 1.3971(2) 1.09150(16) 0.0245(6) Uani 1 1 d . . . H8BA H 0.9666 1.4307 1.1465 0.029 Uiso 1 1 calc R . . C9B C 0.6858(5) 1.4022(3) 1.08116(19) 0.0310(6) Uani 1 1 d . . . H9BA H 0.5888 1.4912 1.0823 0.046 Uiso 1 1 calc R . . H9BB H 0.6316 1.3440 1.1292 0.046 Uiso 1 1 calc R . . H9BC H 0.6686 1.3748 1.0255 0.046 Uiso 1 1 calc R . . C10B C 1.0654(5) 0.7252(2) 1.31115(16) 0.0277(6) Uani 1 1 d . . . C11B C 1.1844(6) 0.6478(3) 1.23694(18) 0.0353(7) Uani 1 1 d . . . H11D H 1.1092 0.6900 1.1820 0.053 Uiso 1 1 calc R . . H11E H 1.1643 0.5590 1.2504 0.053 Uiso 1 1 calc R . . H11F H 1.3553 0.6452 1.2313 0.053 Uiso 1 1 calc R . . C12B C 1.1796(6) 0.6622(3) 1.39935(17) 0.0361(7) Uani 1 1 d . . . H12D H 1.1008 0.7132 1.4451 0.054 Uiso 1 1 calc R . . H12E H 1.3503 0.6600 1.3947 0.054 Uiso 1 1 calc R . . H12F H 1.1601 0.5735 1.4141 0.054 Uiso 1 1 calc R . . C13B C 0.7931(5) 0.7415(3) 1.31969(18) 0.0320(6) Uani 1 1 d . . . H13D H 0.7227 0.7820 1.2636 0.048 Uiso 1 1 calc R . . H13E H 0.7242 0.7968 1.3643 0.048 Uiso 1 1 calc R . . H13F H 0.7588 0.6563 1.3366 0.048 Uiso 1 1 calc R . . C14B C 1.1229(6) 1.1408(3) 1.29495(18) 0.0366(7) Uani 1 1 d . . . H14B H 1.1957 1.0798 1.3459 0.044 Uiso 1 1 calc R . . H14D H 1.2126 1.2089 1.2817 0.044 Uiso 1 1 calc R . . C15B C 0.8603(7) 1.2069(3) 1.32218(19) 0.0481(9) Uani 1 1 d . . . H15B H 0.7685 1.2428 1.2682 0.058 Uiso 1 1 calc R . . C16B C 0.7310(6) 1.1142(3) 1.3811(3) 0.0544(9) Uani 1 1 d . . . H16D H 0.5678 1.1617 1.3958 0.082 Uiso 1 1 calc R . . H16E H 0.8177 1.0791 1.4348 0.082 Uiso 1 1 calc R . . H16F H 0.7253 1.0427 1.3503 0.082 Uiso 1 1 calc R . . C17B C 0.8599(12) 1.3210(4) 1.3720(4) 0.123(3) Uani 1 1 d . . . H17D H 0.6951 1.3627 1.3893 0.185 Uiso 1 1 calc R . . H17E H 0.9305 1.3846 1.3340 0.185 Uiso 1 1 calc R . . H17F H 0.9538 1.2875 1.4242 0.185 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 O1A 0.0514(13) 0.0335(10) 0.0305(10) 0.0043(8) -0.0143(9) -0.0225(10) N1A 0.0305(13) 0.0217(11) 0.0279(11) -0.0058(9) -0.0043(9) -0.0111(10) C1A 0.0162(14) 0.0191(12) 0.0306(14) -0.0031(10) -0.0030(11) -0.0057(11) O2A 0.0208(10) 0.0235(8) 0.0363(10) -0.0077(7) -0.0057(8) -0.0047(7) N2A 0.0191(12) 0.0218(10) 0.0235(11) -0.0051(8) -0.0013(8) -0.0058(9) C2A 0.0150(13) 0.0208(12) 0.0346(14) -0.0075(11) 0.0011(11) -0.0014(10) O3A 0.0228(10) 0.0239(9) 0.0325(9) -0.0134(7) 0.0002(7) -0.0051(8) C3A 0.0225(15) 0.0206(12) 0.0289(13) -0.0025(10) 0.0008(11) -0.0065(11) C4A 0.0179(14) 0.0253(13) 0.0246(13) -0.0073(10) 0.0003(10) -0.0080(11) C5A 0.0156(13) 0.0216(12) 0.0275(13) -0.0076(10) -0.0005(10) -0.0026(11) C6A 0.0271(15) 0.0271(13) 0.0297(14) -0.0062(11) 0.0010(11) -0.0114(12) C7A 0.0313(16) 0.0233(13) 0.0256(13) -0.0041(11) 0.0027(12) -0.0113(12) C8A 0.0249(15) 0.0200(12) 0.0265(13) -0.0055(10) -0.0022(10) -0.0033(11) C9A 0.0437(18) 0.0202(13) 0.0342(14) -0.0025(11) -0.0023(12) -0.0124(12) C10A 0.0242(16) 0.0223(13) 0.0455(16) -0.0152(12) 0.0031(12) -0.0016(12) C11A 0.0298(17) 0.0388(16) 0.0465(17) -0.0161(14) 0.0067(13) -0.0083(14) C12A 0.0316(18) 0.0298(15) 0.0531(18) -0.0198(13) -0.0002(13) -0.0055(13) C13A 0.0312(17) 0.0252(13) 0.0460(17) -0.0088(12) -0.0025(13) -0.0042(12) C14A 0.0265(16) 0.0316(14) 0.0282(14) -0.0078(11) -0.0045(11) -0.0033(12) C15A 0.051(2) 0.0307(15) 0.0266(14) -0.0018(11) -0.0021(13) -0.0088(14) C16A 0.057(2) 0.0416(17) 0.0477(18) -0.0021(14) 0.0162(16) -0.0164(16) C17A 0.102(4) 0.068(3) 0.082(3) 0.041(2) 0.025(3) 0.030(3) O1B 0.0302(11) 0.0320(10) 0.0374(11) 0.0051(8) 0.0029(8) -0.0072(9) N1B 0.0279(14) 0.0166(10) 0.0415(12) -0.0010(9) -0.0006(10) -0.0081(10) C1B 0.0226(15) 0.0193(12) 0.0292(14) -0.0039(11) -0.0029(11) -0.0060(11) O2B 0.0298(11) 0.0228(9) 0.0318(10) -0.0002(7) -0.0079(8) -0.0091(8) N2B 0.0234(12) 0.0211(10) 0.0255(11) 0.0010(8) -0.0051(9) -0.0091(9) C2B 0.0250(15) 0.0176(12) 0.0295(13) -0.0001(10) -0.0046(11) -0.0090(11) O3B 0.0332(11) 0.0221(9) 0.0299(9) 0.0039(7) -0.0076(8) -0.0117(8) C3B 0.0257(16) 0.0209(13) 0.0283(14) 0.0022(11) -0.0019(11) -0.0058(11) C4B 0.0247(15) 0.0253(13) 0.0295(14) 0.0005(11) -0.0060(11) -0.0100(12) C5B 0.0220(14) 0.0177(12) 0.0325(14) -0.0010(10) -0.0060(10) -0.0081(11) C6B 0.0203(15) 0.0202(12) 0.0347(14) -0.0023(11) -0.0010(11) -0.0033(11) C7B 0.0204(15) 0.0251(13) 0.0320(14) -0.0007(11) -0.0033(11) -0.0047(12) C8B 0.0251(15) 0.0193(12) 0.0289(13) -0.0047(10) -0.0005(11) -0.0049(11) C9B 0.0222(16) 0.0254(13) 0.0441(16) -0.0046(12) 0.0002(12) -0.0046(12) C10B 0.0297(16) 0.0207(13) 0.0338(14) 0.0017(11) -0.0006(11) -0.0119(12) C11B 0.0367(18) 0.0278(14) 0.0418(16) -0.0043(12) 0.0031(13) -0.0110(13) C12B 0.0369(18) 0.0340(15) 0.0351(15) 0.0075(12) -0.0028(13) -0.0123(14) C13B 0.0286(16) 0.0322(14) 0.0358(15) -0.0020(12) 0.0021(12) -0.0116(12) C14B 0.053(2) 0.0309(15) 0.0334(15) 0.0009(12) -0.0127(14) -0.0239(15) C15B 0.078(3) 0.0333(16) 0.0271(15) -0.0053(12) -0.0080(15) -0.0019(16) C16B 0.039(2) 0.051(2) 0.080(2) -0.0198(18) -0.0013(17) -0.0166(17) C17B 0.213(7) 0.065(3) 0.112(4) -0.055(3) 0.103(4) -0.078(4) _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 O1A C7A 1.225(3) . ? N1A C7A 1.359(3) . ? N1A C8A 1.462(3) . ? N1A H1AA 0.8600 . ? C1A O2A 1.238(3) . ? C1A N2A 1.372(3) . ? C1A C2A 1.466(4) . ? N2A C4A 1.461(3) . ? N2A C5A 1.462(3) . ? C2A C3A 1.337(4) . ? C2A H2AA 0.9300 . ? O3A C3A 1.341(3) . ? O3A C10A 1.478(3) . ? C3A C4A 1.503(3) . ? C4A C14A 1.530(3) . ? C4A H4AA 0.9800 . ? C5A C6A 1.527(4) . ? C5A C8A 1.555(3) . ? C5A H5AA 0.9800 . ? C6A C7A 1.509(4) . ? C6A H6AA 0.9700 . ? C6A H6AB 0.9700 . ? C8A C9A 1.513(4) . ? C8A H8AA 0.9800 . ? C9A H9AA 0.9600 . ? C9A H9AB 0.9600 . ? C9A H9AC 0.9600 . ? C10A C12A 1.518(4) . ? C10A C11A 1.517(4) . ? C10A C13A 1.524(4) . ? C11A H11A 0.9600 . ? C11A H11B 0.9600 . ? C11A H11C 0.9600 . ? C12A H12A 0.9600 . ? C12A H12B 0.9600 . ? C12A H12C 0.9600 . ? C13A H13A 0.9600 . ? C13A H13B 0.9600 . ? C13A H13C 0.9600 . ? C14A C15A 1.525(4) . ? C14A H14A 0.9700 . ? C14A H14C 0.9700 . ? C15A C17A 1.515(5) . ? C15A C16A 1.522(4) . ? C15A H15A 0.9800 . ? C16A H16A 0.9600 . ? C16A H16B 0.9600 . ? C16A H16C 0.9600 . ? C17A H17A 0.9600 . ? C17A H17B 0.9600 . ? C17A H17C 0.9600 . ? O1B C7B 1.222(3) . ? N1B C7B 1.353(3) . ? N1B C8B 1.469(3) . ? N1B H1BA 0.8600 . ? C1B O2B 1.237(3) . ? C1B N2B 1.377(3) . ? C1B C2B 1.469(3) . ? N2B C5B 1.458(3) . ? N2B C4B 1.468(3) . ? C2B C3B 1.329(4) . ? C2B H2BA 0.9300 . ? O3B C3B 1.342(3) . ? O3B C10B 1.490(3) . ? C3B C4B 1.513(3) . ? C4B C14B 1.529(4) . ? C4B H4BA 0.9800 . ? C5B C6B 1.517(3) . ? C5B C8B 1.555(3) . ? C5B H5BA 0.9800 . ? C6B C7B 1.508(3) . ? C6B H6BA 0.9700 . ? C6B H6BB 0.9700 . ? C8B C9B 1.512(4) . ? C8B H8BA 0.9800 . ? C9B H9BA 0.9600 . ? C9B H9BB 0.9600 . ? C9B H9BC 0.9600 . ? C10B C13B 1.507(4) . ? C10B C11B 1.513(4) . ? C10B C12B 1.516(4) . ? C11B H11D 0.9600 . ? C11B H11E 0.9600 . ? C11B H11F 0.9600 . ? C12B H12D 0.9600 . ? C12B H12E 0.9600 . ? C12B H12F 0.9600 . ? C13B H13D 0.9600 . ? C13B H13E 0.9600 . ? C13B H13F 0.9600 . ? C14B C15B 1.528(5) . ? C14B H14B 0.9700 . ? C14B H14D 0.9700 . ? C15B C16B 1.509(5) . ? C15B C17B 1.525(5) . ? C15B H15B 0.9800 . ? C16B H16D 0.9600 . ? C16B H16E 0.9600 . ? C16B H16F 0.9600 . ? C17B H17D 0.9600 . ? C17B H17E 0.9600 . ? C17B H17F 0.9600 . ? 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 C7A N1A C8A 114.3(2) . . ? C7A N1A H1AA 122.8 . . ? C8A N1A H1AA 122.8 . . ? O2A C1A N2A 124.4(2) . . ? O2A C1A C2A 127.0(2) . . ? N2A C1A C2A 108.6(2) . . ? C1A N2A C4A 110.21(19) . . ? C1A N2A C5A 122.8(2) . . ? C4A N2A C5A 119.2(2) . . ? C3A C2A C1A 107.3(2) . . ? C3A C2A H2AA 126.4 . . ? C1A C2A H2AA 126.4 . . ? C3A O3A C10A 121.37(19) . . ? C2A C3A O3A 134.0(2) . . ? C2A C3A C4A 111.5(2) . . ? O3A C3A C4A 114.5(2) . . ? N2A C4A C3A 102.03(19) . . ? N2A C4A C14A 113.56(19) . . ? C3A C4A C14A 116.2(2) . . ? N2A C4A H4AA 108.2 . . ? C3A C4A H4AA 108.2 . . ? C14A C4A H4AA 108.2 . . ? N2A C5A C6A 112.9(2) . . ? N2A C5A C8A 115.40(19) . . ? C6A C5A C8A 102.55(18) . . ? N2A C5A H5AA 108.5 . . ? C6A C5A H5AA 108.5 . . ? C8A C5A H5AA 108.5 . . ? C7A C6A C5A 105.6(2) . . ? C7A C6A H6AA 110.6 . . ? C5A C6A H6AA 110.6 . . ? C7A C6A H6AB 110.6 . . ? C5A C6A H6AB 110.6 . . ? H6AA C6A H6AB 108.8 . . ? O1A C7A N1A 125.9(2) . . ? O1A C7A C6A 127.3(2) . . ? N1A C7A C6A 106.7(2) . . ? N1A C8A C9A 112.2(2) . . ? N1A C8A C5A 103.86(19) . . ? C9A C8A C5A 116.7(2) . . ? N1A C8A H8AA 107.9 . . ? C9A C8A H8AA 107.9 . . ? C5A C8A H8AA 107.9 . . ? C8A C9A H9AA 109.5 . . ? C8A C9A H9AB 109.5 . . ? H9AA C9A H9AB 109.5 . . ? C8A C9A H9AC 109.5 . . ? H9AA C9A H9AC 109.5 . . ? H9AB C9A H9AC 109.5 . . ? O3A C10A C12A 102.1(2) . . ? O3A C10A C11A 109.0(2) . . ? C12A C10A C11A 111.0(2) . . ? O3A C10A C13A 110.9(2) . . ? C12A C10A C13A 110.1(2) . . ? C11A C10A C13A 113.3(2) . . ? C10A C11A H11A 109.5 . . ? C10A C11A H11B 109.5 . . ? H11A C11A H11B 109.5 . . ? C10A C11A H11C 109.5 . . ? H11A C11A H11C 109.5 . . ? H11B C11A H11C 109.5 . . ? C10A C12A H12A 109.5 . . ? C10A C12A H12B 109.5 . . ? H12A C12A H12B 109.5 . . ? C10A C12A H12C 109.5 . . ? H12A C12A H12C 109.5 . . ? H12B C12A H12C 109.5 . . ? C10A C13A H13A 109.5 . . ? C10A C13A H13B 109.5 . . ? H13A C13A H13B 109.5 . . ? C10A C13A H13C 109.5 . . ? H13A C13A H13C 109.5 . . ? H13B C13A H13C 109.5 . . ? C15A C14A C4A 116.9(2) . . ? C15A C14A H14A 108.1 . . ? C4A C14A H14A 108.1 . . ? C15A C14A H14C 108.1 . . ? C4A C14A H14C 108.1 . . ? H14A C14A H14C 107.3 . . ? C17A C15A C16A 109.2(3) . . ? C17A C15A C14A 110.5(3) . . ? C16A C15A C14A 113.6(2) . . ? C17A C15A H15A 107.8 . . ? C16A C15A H15A 107.8 . . ? C14A C15A H15A 107.8 . . ? C15A C16A H16A 109.5 . . ? C15A C16A H16B 109.5 . . ? H16A C16A H16B 109.5 . . ? C15A C16A H16C 109.5 . . ? H16A C16A H16C 109.5 . . ? H16B C16A H16C 109.5 . . ? C15A C17A H17A 109.5 . . ? C15A C17A H17B 109.5 . . ? H17A C17A H17B 109.5 . . ? C15A C17A H17C 109.5 . . ? H17A C17A H17C 109.5 . . ? H17B C17A H17C 109.5 . . ? C7B N1B C8B 114.3(2) . . ? C7B N1B H1BA 122.9 . . ? C8B N1B H1BA 122.9 . . ? O2B C1B N2B 125.6(2) . . ? O2B C1B C2B 126.3(2) . . ? N2B C1B C2B 108.0(2) . . ? C1B N2B C5B 126.57(19) . . ? C1B N2B C4B 110.44(19) . . ? C5B N2B C4B 120.34(19) . . ? C3B C2B C1B 108.3(2) . . ? C3B C2B H2BA 125.9 . . ? C1B C2B H2BA 125.9 . . ? C3B O3B C10B 120.83(19) . . ? C2B C3B O3B 134.7(2) . . ? C2B C3B C4B 111.2(2) . . ? O3B C3B C4B 114.1(2) . . ? N2B C4B C3B 101.76(19) . . ? N2B C4B C14B 113.6(2) . . ? C3B C4B C14B 117.1(2) . . ? N2B C4B H4BA 108.0 . . ? C3B C4B H4BA 108.0 . . ? C14B C4B H4BA 108.0 . . ? N2B C5B C6B 116.7(2) . . ? N2B C5B C8B 116.6(2) . . ? C6B C5B C8B 104.2(2) . . ? N2B C5B H5BA 106.2 . . ? C6B C5B H5BA 106.2 . . ? C8B C5B H5BA 106.2 . . ? C7B C6B C5B 104.1(2) . . ? C7B C6B H6BA 110.9 . . ? C5B C6B H6BA 110.9 . . ? C7B C6B H6BB 110.9 . . ? C5B C6B H6BB 110.9 . . ? H6BA C6B H6BB 109.0 . . ? O1B C7B N1B 126.6(2) . . ? O1B C7B C6B 125.4(2) . . ? N1B C7B C6B 107.9(2) . . ? N1B C8B C9B 112.0(2) . . ? N1B C8B C5B 100.77(19) . . ? C9B C8B C5B 115.6(2) . . ? N1B C8B H8BA 109.4 . . ? C9B C8B H8BA 109.4 . . ? C5B C8B H8BA 109.4 . . ? C8B C9B H9BA 109.5 . . ? C8B C9B H9BB 109.5 . . ? H9BA C9B H9BB 109.5 . . ? C8B C9B H9BC 109.5 . . ? H9BA C9B H9BC 109.5 . . ? H9BB C9B H9BC 109.5 . . ? O3B C10B C13B 111.2(2) . . ? O3B C10B C11B 109.8(2) . . ? C13B C10B C11B 112.5(2) . . ? O3B C10B C12B 101.42(19) . . ? C13B C10B C12B 110.2(2) . . ? C11B C10B C12B 111.3(2) . . ? C10B C11B H11D 109.5 . . ? C10B C11B H11E 109.5 . . ? H11D C11B H11E 109.5 . . ? C10B C11B H11F 109.5 . . ? H11D C11B H11F 109.5 . . ? H11E C11B H11F 109.5 . . ? C10B C12B H12D 109.5 . . ? C10B C12B H12E 109.5 . . ? H12D C12B H12E 109.5 . . ? C10B C12B H12F 109.5 . . ? H12D C12B H12F 109.5 . . ? H12E C12B H12F 109.5 . . ? C10B C13B H13D 109.5 . . ? C10B C13B H13E 109.5 . . ? H13D C13B H13E 109.5 . . ? C10B C13B H13F 109.5 . . ? H13D C13B H13F 109.5 . . ? H13E C13B H13F 109.5 . . ? C15B C14B C4B 117.1(2) . . ? C15B C14B H14B 108.0 . . ? C4B C14B H14B 108.0 . . ? C15B C14B H14D 108.0 . . ? C4B C14B H14D 108.0 . . ? H14B C14B H14D 107.3 . . ? C16B C15B C17B 108.1(3) . . ? C16B C15B C14B 113.7(3) . . ? C17B C15B C14B 109.2(3) . . ? C16B C15B H15B 108.6 . . ? C17B C15B H15B 108.6 . . ? C14B C15B H15B 108.6 . . ? C15B C16B H16D 109.5 . . ? C15B C16B H16E 109.5 . . ? H16D C16B H16E 109.5 . . ? C15B C16B H16F 109.5 . . ? H16D C16B H16F 109.5 . . ? H16E C16B H16F 109.5 . . ? C15B C17B H17D 109.5 . . ? C15B C17B H17E 109.5 . . ? H17D C17B H17E 109.5 . . ? C15B C17B H17F 109.5 . . ? H17D C17B H17F 109.5 . . ? H17E C17B H17F 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 O2A C1A N2A C4A -171.1(2) . . . . ? C2A C1A N2A C4A 7.1(3) . . . . ? O2A C1A N2A C5A -22.2(4) . . . . ? C2A C1A N2A C5A 156.0(2) . . . . ? O2A C1A C2A C3A 171.7(2) . . . . ? N2A C1A C2A C3A -6.4(3) . . . . ? C1A C2A C3A O3A -175.3(2) . . . . ? C1A C2A C3A C4A 3.3(3) . . . . ? C10A O3A C3A C2A 6.8(4) . . . . ? C10A O3A C3A C4A -171.7(2) . . . . ? C1A N2A C4A C3A -4.9(2) . . . . ? C5A N2A C4A C3A -155.08(19) . . . . ? C1A N2A C4A C14A -130.7(2) . . . . ? C5A N2A C4A C14A 79.1(3) . . . . ? C2A C3A C4A N2A 0.8(3) . . . . ? O3A C3A C4A N2A 179.69(18) . . . . ? C2A C3A C4A C14A 124.9(2) . . . . ? O3A C3A C4A C14A -56.2(3) . . . . ? C1A N2A C5A C6A -46.2(3) . . . . ? C4A N2A C5A C6A 100.0(2) . . . . ? C1A N2A C5A C8A 71.3(3) . . . . ? C4A N2A C5A C8A -142.4(2) . . . . ? N2A C5A C6A C7A 98.4(2) . . . . ? C8A C5A C6A C7A -26.4(2) . . . . ? C8A N1A C7A O1A 174.4(3) . . . . ? C8A N1A C7A C6A -8.2(3) . . . . ? C5A C6A C7A O1A -160.5(3) . . . . ? C5A C6A C7A N1A 22.2(3) . . . . ? C7A N1A C8A C9A -135.7(2) . . . . ? C7A N1A C8A C5A -8.8(3) . . . . ? N2A C5A C8A N1A -101.8(2) . . . . ? C6A C5A C8A N1A 21.4(2) . . . . ? N2A C5A C8A C9A 22.2(3) . . . . ? C6A C5A C8A C9A 145.4(2) . . . . ? C3A O3A C10A C12A 167.4(2) . . . . ? C3A O3A C10A C11A -75.2(3) . . . . ? C3A O3A C10A C13A 50.1(3) . . . . ? N2A C4A C14A C15A 52.9(3) . . . . ? C3A C4A C14A C15A -65.0(3) . . . . ? C4A C14A C15A C17A -158.5(3) . . . . ? C4A C14A C15A C16A 78.4(3) . . . . ? O2B C1B N2B C5B -12.5(4) . . . . ? C2B C1B N2B C5B 166.7(2) . . . . ? O2B C1B N2B C4B -173.9(2) . . . . ? C2B C1B N2B C4B 5.3(3) . . . . ? O2B C1B C2B C3B 176.4(3) . . . . ? N2B C1B C2B C3B -2.9(3) . . . . ? C1B C2B C3B O3B -178.8(3) . . . . ? C1B C2B C3B C4B -0.6(3) . . . . ? C10B O3B C3B C2B 5.6(4) . . . . ? C10B O3B C3B C4B -172.5(2) . . . . ? C1B N2B C4B C3B -5.4(3) . . . . ? C5B N2B C4B C3B -168.1(2) . . . . ? C1B N2B C4B C14B -132.1(2) . . . . ? C5B N2B C4B C14B 65.1(3) . . . . ? C2B C3B C4B N2B 3.6(3) . . . . ? O3B C3B C4B N2B -177.9(2) . . . . ? C2B C3B C4B C14B 128.0(3) . . . . ? O3B C3B C4B C14B -53.4(3) . . . . ? C1B N2B C5B C6B -37.3(4) . . . . ? C4B N2B C5B C6B 122.4(2) . . . . ? C1B N2B C5B C8B 86.6(3) . . . . ? C4B N2B C5B C8B -113.6(2) . . . . ? N2B C5B C6B C7B 157.2(2) . . . . ? C8B C5B C6B C7B 27.2(2) . . . . ? C8B N1B C7B O1B 175.8(2) . . . . ? C8B N1B C7B C6B -3.8(3) . . . . ? C5B C6B C7B O1B 165.0(2) . . . . ? C5B C6B C7B N1B -15.4(3) . . . . ? C7B N1B C8B C9B -102.8(2) . . . . ? C7B N1B C8B C5B 20.6(3) . . . . ? N2B C5B C8B N1B -158.5(2) . . . . ? C6B C5B C8B N1B -28.4(2) . . . . ? N2B C5B C8B C9B -37.7(3) . . . . ? C6B C5B C8B C9B 92.5(2) . . . . ? C3B O3B C10B C13B -62.5(3) . . . . ? C3B O3B C10B C11B 62.5(3) . . . . ? C3B O3B C10B C12B -179.7(2) . . . . ? N2B C4B C14B C15B 54.6(3) . . . . ? C3B C4B C14B C15B -63.6(3) . . . . ? C4B C14B C15B C16B 83.1(3) . . . . ? C4B C14B C15B C17B -156.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 59.93 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.187 _refine_diff_density_min -0.205 _refine_diff_density_rms 0.038 # Attachment '- compound 7.cif' data_kb _database_code_depnum_ccdc_archive 'CCDC 854833' #TrackingRef '- compound 7.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H30 Cl3 N3 O4' _chemical_formula_weight 482.82 _chemical_absolute_configuration ab 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' Cl Cl 0.3639 0.7018 '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 13.1883(6) _cell_length_b 6.5039(3) _cell_length_c 14.5084(7) _cell_angle_alpha 90.00 _cell_angle_beta 100.899(3) _cell_angle_gamma 90.00 _cell_volume 1222.02(10) _cell_formula_units_Z 2 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 8144 _cell_measurement_theta_min 3.10 _cell_measurement_theta_max 61.05 _exptl_crystal_description 'plate ' _exptl_crystal_colour 'colorless ' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.312 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 508 _exptl_absorpt_coefficient_mu 3.645 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4077 _exptl_absorpt_correction_T_max 0.9307 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'MWPC area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 25392 _diffrn_reflns_av_R_equivalents 0.0559 _diffrn_reflns_av_sigmaI/netI 0.0441 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.10 _diffrn_reflns_theta_max 59.98 _reflns_number_total 3561 _reflns_number_gt 3060 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker FRAMBO' _computing_cell_refinement 'Bruker FRAMBO' _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^)+(0.0450P)^2^+0.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.026(13) _refine_ls_number_reflns 3561 _refine_ls_number_parameters 277 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0393 _refine_ls_R_factor_gt 0.0330 _refine_ls_wR_factor_ref 0.0773 _refine_ls_wR_factor_gt 0.0755 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _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 Cl1 Cl 0.42108(7) 0.42247(13) 0.50217(6) 0.0494(3) Uani 1 1 d . . . Cl2 Cl 0.31776(7) 0.07774(14) 0.39856(6) 0.0455(2) Uani 1 1 d . . . Cl3 Cl 0.20323(7) 0.34862(14) 0.49711(6) 0.0493(3) Uani 1 1 d . . . O1 O 0.09399(14) 1.3806(3) 0.04932(13) 0.0275(5) Uani 1 1 d . . . O2 O 0.28557(14) 0.6487(3) 0.28038(13) 0.0234(5) Uani 1 1 d . . . O3 O 0.61044(14) 0.8114(3) 0.02797(13) 0.0271(5) Uani 1 1 d . . . O4 O 0.86848(14) 0.7758(3) 0.30663(14) 0.0269(5) Uani 1 1 d . . . N1 N 0.10353(17) 1.0301(3) 0.03675(16) 0.0232(6) Uani 1 1 d . . . H1 H 0.0408 1.0105 0.0045 0.028 Uiso 1 1 calc R . . N2 N 0.34705(15) 0.8579(3) 0.17687(14) 0.0173(5) Uani 1 1 d . . . N3 N 0.61462(16) 0.7079(4) 0.17989(15) 0.0212(5) Uani 1 1 d . . . C1 C 0.1396(2) 1.2160(4) 0.06621(19) 0.0203(7) Uani 1 1 d . . . C2 C 0.2476(2) 1.1892(4) 0.12328(19) 0.0191(6) Uani 1 1 d . . . H2A H 0.2587 1.2767 0.1801 0.023 Uiso 1 1 calc R . . H2B H 0.3008 1.2212 0.0856 0.023 Uiso 1 1 calc R . . C3 C 0.24808(19) 0.9610(4) 0.14856(19) 0.0166(6) Uani 1 1 d . . . H3 H 0.2111 0.9484 0.2024 0.020 Uiso 1 1 calc R . . C4 C 0.17740(19) 0.8620(4) 0.06281(18) 0.0207(6) Uani 1 1 d . . . H4 H 0.1414 0.7398 0.0833 0.025 Uiso 1 1 calc R . . C5 C 0.2306(2) 0.8024(5) -0.01761(19) 0.0273(7) Uani 1 1 d . . . H5A H 0.2791 0.6897 0.0024 0.041 Uiso 1 1 calc R . . H5B H 0.2683 0.9212 -0.0355 0.041 Uiso 1 1 calc R . . H5C H 0.1787 0.7580 -0.0715 0.041 Uiso 1 1 calc R . . C6 C 0.3556(2) 0.7069(4) 0.24162(19) 0.0198(6) Uani 1 1 d . . . C7 C 0.46452(19) 0.6264(4) 0.25819(18) 0.0196(7) Uani 1 1 d . . . H7A H 0.4659 0.4749 0.2650 0.024 Uiso 1 1 calc R . . H7B H 0.5068 0.6887 0.3150 0.024 Uiso 1 1 calc R . . C8 C 0.5024(2) 0.6926(4) 0.16979(19) 0.0189(6) Uani 1 1 d . . . H8 H 0.4770 0.5905 0.1192 0.023 Uiso 1 1 calc R . . C9 C 0.44489(18) 0.8998(4) 0.14319(18) 0.0177(6) Uani 1 1 d . . . H9 H 0.4307 0.9186 0.0735 0.021 Uiso 1 1 calc R . . C10 C 0.5013(2) 1.0861(5) 0.1910(2) 0.0252(7) Uani 1 1 d . . . H10A H 0.5663 1.1052 0.1686 0.038 Uiso 1 1 calc R . . H10B H 0.5160 1.0648 0.2591 0.038 Uiso 1 1 calc R . . H10C H 0.4580 1.2086 0.1761 0.038 Uiso 1 1 calc R . . C11 C 0.6584(2) 0.7804(4) 0.10810(19) 0.0213(7) Uani 1 1 d . . . C12 C 0.7683(2) 0.8158(5) 0.14502(19) 0.0232(7) Uani 1 1 d . . . H12 H 0.8180 0.8618 0.1100 0.028 Uiso 1 1 calc R . . C13 C 0.7864(2) 0.7721(4) 0.2361(2) 0.0219(7) Uani 1 1 d . . . C14 C 0.6899(2) 0.6928(5) 0.26714(19) 0.0216(6) Uani 1 1 d . . . H14 H 0.6703 0.7865 0.3155 0.026 Uiso 1 1 calc R . . C15 C 0.7064(2) 0.4753(5) 0.3059(2) 0.0297(7) Uani 1 1 d . . . H15A H 0.7655 0.4737 0.3582 0.045 Uiso 1 1 calc R . . H15B H 0.7199 0.3826 0.2564 0.045 Uiso 1 1 calc R . . H15C H 0.6444 0.4296 0.3281 0.045 Uiso 1 1 calc R . . C16 C 0.9745(2) 0.8219(5) 0.2914(2) 0.0273(7) Uani 1 1 d . . . C17 C 1.0057(2) 0.6625(5) 0.2266(2) 0.0385(8) Uani 1 1 d . . . H17A H 1.0802 0.6718 0.2282 0.058 Uiso 1 1 calc R . . H17B H 0.9684 0.6869 0.1625 0.058 Uiso 1 1 calc R . . H17C H 0.9888 0.5252 0.2471 0.058 Uiso 1 1 calc R . . C18 C 1.0371(2) 0.7997(6) 0.3901(2) 0.0427(9) Uani 1 1 d . . . H18A H 1.1099 0.8287 0.3897 0.064 Uiso 1 1 calc R . . H18B H 1.0303 0.6590 0.4125 0.064 Uiso 1 1 calc R . . H18C H 1.0115 0.8969 0.4320 0.064 Uiso 1 1 calc R . . C19 C 0.9798(3) 1.0410(5) 0.2575(2) 0.0402(9) Uani 1 1 d . . . H19A H 1.0522 1.0808 0.2616 0.060 Uiso 1 1 calc R . . H19B H 0.9472 1.1330 0.2967 0.060 Uiso 1 1 calc R . . H19C H 0.9436 1.0511 0.1921 0.060 Uiso 1 1 calc R . . C20 C 0.3041(2) 0.3333(5) 0.4339(2) 0.0339(8) Uani 1 1 d . . . H20 H 0.2864 0.4214 0.3766 0.041 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 Cl1 0.0463(6) 0.0528(6) 0.0439(5) 0.0061(4) -0.0045(4) -0.0143(4) Cl2 0.0412(5) 0.0485(5) 0.0470(5) -0.0085(4) 0.0087(4) 0.0006(4) Cl3 0.0430(5) 0.0632(6) 0.0449(5) 0.0093(5) 0.0164(4) 0.0169(4) O1 0.0140(11) 0.0232(12) 0.0430(12) 0.0015(10) -0.0002(8) 0.0062(9) O2 0.0143(11) 0.0262(12) 0.0312(11) 0.0084(9) 0.0079(9) 0.0005(8) O3 0.0198(11) 0.0393(13) 0.0229(11) 0.0006(10) 0.0058(9) 0.0028(9) O4 0.0135(11) 0.0380(13) 0.0290(11) 0.0034(9) 0.0040(8) -0.0001(8) N1 0.0089(13) 0.0267(16) 0.0309(14) 0.0000(11) -0.0039(10) -0.0001(10) N2 0.0119(12) 0.0179(12) 0.0226(12) 0.0004(10) 0.0046(9) 0.0034(9) N3 0.0106(13) 0.0308(14) 0.0223(13) 0.0012(11) 0.0038(9) 0.0051(10) C1 0.0128(15) 0.0242(18) 0.0244(16) -0.0011(13) 0.0052(12) -0.0017(13) C2 0.0138(15) 0.0215(16) 0.0217(15) 0.0013(13) 0.0026(11) 0.0010(13) C3 0.0108(15) 0.0177(15) 0.0219(15) 0.0039(12) 0.0042(11) 0.0043(11) C4 0.0120(15) 0.0201(16) 0.0293(16) 0.0013(13) 0.0021(11) 0.0002(12) C5 0.0235(17) 0.0265(17) 0.0296(17) -0.0063(14) -0.0008(12) 0.0008(13) C6 0.0201(17) 0.0186(15) 0.0208(16) -0.0028(13) 0.0043(12) 0.0009(13) C7 0.0150(16) 0.0193(17) 0.0243(16) 0.0003(12) 0.0031(12) 0.0043(11) C8 0.0131(15) 0.0194(15) 0.0252(16) -0.0045(13) 0.0065(11) 0.0013(12) C9 0.0095(14) 0.0212(16) 0.0238(15) 0.0019(12) 0.0066(11) -0.0010(11) C10 0.0182(17) 0.0215(16) 0.0353(17) -0.0018(14) 0.0036(12) -0.0037(13) C11 0.0197(16) 0.0249(17) 0.0218(17) 0.0000(13) 0.0103(13) 0.0046(12) C12 0.0129(16) 0.0284(17) 0.0294(17) 0.0013(14) 0.0066(12) 0.0017(12) C13 0.0154(16) 0.0251(17) 0.0249(17) -0.0004(13) 0.0029(12) 0.0020(12) C14 0.0157(16) 0.0283(17) 0.0208(16) 0.0019(14) 0.0034(11) 0.0012(13) C15 0.0203(18) 0.0322(18) 0.0356(18) 0.0067(14) 0.0029(13) -0.0013(13) C16 0.0131(16) 0.0323(19) 0.0370(18) 0.0034(15) 0.0058(12) -0.0035(13) C17 0.0208(19) 0.042(2) 0.055(2) -0.0039(17) 0.0126(15) 0.0012(14) C18 0.0175(18) 0.065(3) 0.043(2) 0.0117(19) -0.0012(14) -0.0052(16) C19 0.028(2) 0.036(2) 0.056(2) 0.0093(17) 0.0062(16) -0.0020(15) C20 0.0337(19) 0.039(2) 0.0280(17) 0.0086(16) 0.0034(13) -0.0029(16) _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 Cl1 C20 1.766(3) . ? Cl2 C20 1.759(3) . ? Cl3 C20 1.756(3) . ? O1 C1 1.230(3) . ? O2 C6 1.228(3) . ? O3 C11 1.230(3) . ? O4 C13 1.342(3) . ? O4 C16 1.487(3) . ? N1 C1 1.339(4) . ? N1 C4 1.466(3) . ? N1 H1 0.8800 . ? N2 C6 1.349(3) . ? N2 C3 1.456(3) . ? N2 C9 1.489(3) . ? N3 C11 1.367(3) . ? N3 C14 1.457(3) . ? N3 C8 1.462(3) . ? C1 C2 1.516(4) . ? C2 C3 1.529(4) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.547(4) . ? C3 H3 1.0000 . ? C4 C5 1.521(4) . ? C4 H4 1.0000 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 C7 1.505(4) . ? C7 C8 1.524(4) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.559(4) . ? C8 H8 1.0000 . ? C9 C10 1.519(4) . ? C9 H9 1.0000 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.466(4) . ? C12 C13 1.329(4) . ? C12 H12 0.9500 . ? C13 C14 1.518(4) . ? C14 C15 1.523(4) . ? C14 H14 1.0000 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.508(4) . ? C16 C19 1.513(4) . ? C16 C18 1.519(4) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20 1.0000 . ? 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 C13 O4 C16 122.4(2) . . ? C1 N1 C4 114.4(2) . . ? C1 N1 H1 122.8 . . ? C4 N1 H1 122.8 . . ? C6 N2 C3 119.0(2) . . ? C6 N2 C9 113.5(2) . . ? C3 N2 C9 127.6(2) . . ? C11 N3 C14 111.6(2) . . ? C11 N3 C8 120.8(2) . . ? C14 N3 C8 126.4(2) . . ? O1 C1 N1 126.3(2) . . ? O1 C1 C2 125.6(3) . . ? N1 C1 C2 108.1(2) . . ? C1 C2 C3 101.8(2) . . ? C1 C2 H2A 111.4 . . ? C3 C2 H2A 111.4 . . ? C1 C2 H2B 111.4 . . ? C3 C2 H2B 111.4 . . ? H2A C2 H2B 109.3 . . ? N2 C3 C2 118.6(2) . . ? N2 C3 C4 114.0(2) . . ? C2 C3 C4 103.7(2) . . ? N2 C3 H3 106.6 . . ? C2 C3 H3 106.6 . . ? C4 C3 H3 106.6 . . ? N1 C4 C5 111.9(2) . . ? N1 C4 C3 99.6(2) . . ? C5 C4 C3 115.3(2) . . ? N1 C4 H4 109.9 . . ? C5 C4 H4 109.9 . . ? C3 C4 H4 109.9 . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? O2 C6 N2 124.9(2) . . ? O2 C6 C7 126.7(3) . . ? N2 C6 C7 108.4(2) . . ? C6 C7 C8 102.9(2) . . ? C6 C7 H7A 111.2 . . ? C8 C7 H7A 111.2 . . ? C6 C7 H7B 111.2 . . ? C8 C7 H7B 111.2 . . ? H7A C7 H7B 109.1 . . ? N3 C8 C7 114.9(2) . . ? N3 C8 C9 113.7(2) . . ? C7 C8 C9 103.3(2) . . ? N3 C8 H8 108.2 . . ? C7 C8 H8 108.2 . . ? C9 C8 H8 108.2 . . ? N2 C9 C10 112.1(2) . . ? N2 C9 C8 99.90(19) . . ? C10 C9 C8 113.8(2) . . ? N2 C9 H9 110.2 . . ? C10 C9 H9 110.2 . . ? C8 C9 H9 110.2 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O3 C11 N3 124.1(3) . . ? O3 C11 C12 128.0(2) . . ? N3 C11 C12 107.9(2) . . ? C13 C12 C11 108.0(2) . . ? C13 C12 H12 126.0 . . ? C11 C12 H12 126.0 . . ? C12 C13 O4 136.2(3) . . ? C12 C13 C14 111.4(2) . . ? O4 C13 C14 112.4(2) . . ? N3 C14 C13 101.0(2) . . ? N3 C14 C15 114.2(2) . . ? C13 C14 C15 110.9(2) . . ? N3 C14 H14 110.1 . . ? C13 C14 H14 110.1 . . ? C15 C14 H14 110.1 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O4 C16 C17 109.2(2) . . ? O4 C16 C19 109.9(2) . . ? C17 C16 C19 114.2(3) . . ? O4 C16 C18 101.5(2) . . ? C17 C16 C18 111.0(3) . . ? C19 C16 C18 110.3(3) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? Cl3 C20 Cl2 109.60(17) . . ? Cl3 C20 Cl1 110.88(17) . . ? Cl2 C20 Cl1 110.31(18) . . ? Cl3 C20 H20 108.7 . . ? Cl2 C20 H20 108.7 . . ? Cl1 C20 H20 108.7 . . ? 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 C4 N1 C1 O1 176.4(3) . . . . ? C4 N1 C1 C2 -2.9(3) . . . . ? O1 C1 C2 C3 161.4(3) . . . . ? N1 C1 C2 C3 -19.3(3) . . . . ? C6 N2 C3 C2 146.2(2) . . . . ? C9 N2 C3 C2 -33.1(4) . . . . ? C6 N2 C3 C4 -91.3(3) . . . . ? C9 N2 C3 C4 89.4(3) . . . . ? C1 C2 C3 N2 160.2(2) . . . . ? C1 C2 C3 C4 32.7(3) . . . . ? C1 N1 C4 C5 -99.1(3) . . . . ? C1 N1 C4 C3 23.3(3) . . . . ? N2 C3 C4 N1 -163.9(2) . . . . ? C2 C3 C4 N1 -33.6(2) . . . . ? N2 C3 C4 C5 -44.0(3) . . . . ? C2 C3 C4 C5 86.3(3) . . . . ? C3 N2 C6 O2 -0.7(4) . . . . ? C9 N2 C6 O2 178.7(2) . . . . ? C3 N2 C6 C7 180.0(2) . . . . ? C9 N2 C6 C7 -0.6(3) . . . . ? O2 C6 C7 C8 159.9(3) . . . . ? N2 C6 C7 C8 -20.8(3) . . . . ? C11 N3 C8 C7 -175.0(2) . . . . ? C14 N3 C8 C7 -8.6(4) . . . . ? C11 N3 C8 C9 -56.2(3) . . . . ? C14 N3 C8 C9 110.2(3) . . . . ? C6 C7 C8 N3 157.3(2) . . . . ? C6 C7 C8 C9 32.9(3) . . . . ? C6 N2 C9 C10 -99.7(3) . . . . ? C3 N2 C9 C10 79.6(3) . . . . ? C6 N2 C9 C8 21.1(3) . . . . ? C3 N2 C9 C8 -159.6(2) . . . . ? N3 C8 C9 N2 -157.6(2) . . . . ? C7 C8 C9 N2 -32.3(2) . . . . ? N3 C8 C9 C10 -37.9(3) . . . . ? C7 C8 C9 C10 87.3(3) . . . . ? C14 N3 C11 O3 -178.2(3) . . . . ? C8 N3 C11 O3 -10.0(4) . . . . ? C14 N3 C11 C12 0.7(3) . . . . ? C8 N3 C11 C12 169.0(2) . . . . ? O3 C11 C12 C13 176.7(3) . . . . ? N3 C11 C12 C13 -2.2(3) . . . . ? C11 C12 C13 O4 -179.1(3) . . . . ? C11 C12 C13 C14 2.8(3) . . . . ? C16 O4 C13 C12 -6.0(5) . . . . ? C16 O4 C13 C14 172.0(2) . . . . ? C11 N3 C14 C13 0.9(3) . . . . ? C8 N3 C14 C13 -166.6(2) . . . . ? C11 N3 C14 C15 -118.1(3) . . . . ? C8 N3 C14 C15 74.4(3) . . . . ? C12 C13 C14 N3 -2.3(3) . . . . ? O4 C13 C14 N3 179.1(2) . . . . ? C12 C13 C14 C15 119.1(3) . . . . ? O4 C13 C14 C15 -59.5(3) . . . . ? C13 O4 C16 C17 -60.9(3) . . . . ? C13 O4 C16 C19 65.2(3) . . . . ? C13 O4 C16 C18 -178.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 59.98 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.184 _refine_diff_density_min -0.238 _refine_diff_density_rms 0.046