# ol991194u.cif data_global _audit_creation_method 'SHELXL-97 and manual editing' #======================================================================= # 1. MANUSCRIPT NUMBER # # ID:OL991194U # # 2. SUBMISSION DETAILS _publ_contact_author_name 'Dr Ivo Vencato' _publ_contact_author_address ; Depto. Qu\'imica - UFSC 88040 - 900 Florian\'opolis, SC Brazil ; _publ_contact_author_email vencato@qmc.ufsc.br _publ_contact_author_fax '55(2148)3316888' _publ_contact_author_phone '55(2148)3316826' _publ_contact_letter ; Please consider this CIF as Supporting Information for Organic Letters. ; _publ_requested_coeditor_name ? _publ_requested_journal ' Organic Letters ' #======================================================================= # 3. TITLE AND AUTHOR LIST _publ_section_title ; The Stereoselective Synthesis of Functionalized trans-2,5-Disubstituted Tetrahydrofurans ; loop_ _publ_author_name _publ_author_address 'Pilli, Ronaldo A.' ; Instituto de Qu\'imica - Unicamp Cx. Postal 6154, 13083-970 - Campinas, SP Brazil ; 'Riatto, Val\'eria B.' ; Instituto de Qu\'imica - Unicamp Cx. Postal 6154, 13083-970 - Campinas, SP Brazil ; 'Vencato, Ivo' ; Depto. Qu\'imica - UFSC 88040-900 - Florian\'opolis, SC Brazil ; #======================================================================= ; _publ_section_references ; Enraf-Nonius (1994). CAD-4 EXPRESS. Version 5.1/1.2. Enraf-Nonius, Delft, The Netherlands. Fair, C. K. (1990). MolEN. An Interactive Intelligent System for Crystal Structure Analysis. Enraf-Nonius, Delft, The Netherlands. Flack, H. D. (1983). Acta Cryst. A39, 876--881. Sheldrick, G. M. (1990). SHELXS97. Program for the Solution of Crystal Structures. Univ. of G\"ottingen, Germany. Sheldrick, G. M. (1997). SHELXL97. Program for the Refinement of Crystal Structures. Univ. of G\"ottingen, Germany. Spek, A. L. (1990). Acta Cryst. A36, C--34. Zsolnai, L., Pritzkow, H. & Hutter, G. (1996). ZORTEP. University of Heidelberg, Germany. ; _publ_section_exptl_refinement ; All H atoms were placed in calculated positions using a riding model, except those involved in H-bonds. ; #===================================================================== data_4c _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H23 N O5' _chemical_formula_weight 333.37 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 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.629(2) _cell_length_b 5.8452(12) _cell_length_c 13.118(3) _cell_angle_alpha 90.00 _cell_angle_beta 102.60(3) _cell_angle_gamma 90.00 _cell_volume 870.2(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10.41 _cell_measurement_theta_max 13.93 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.272 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 356 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Nonius CAD-4 diffractometer' _diffrn_measurement_method \w--2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 0.5 _diffrn_reflns_number 1958 _diffrn_reflns_av_R_equivalents 0.0358 _diffrn_reflns_av_sigmaI/netI 0.0343 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.65 _diffrn_reflns_theta_max 25.97 _reflns_number_total 1877 _reflns_number_gt 1277 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD-4 EXPRESS (Enraf-Nonius, 1994)' _computing_cell_refinement ; SET4 in CAD-4 EXPRESS (Enraf-Nonius, 1994) ; _computing_data_reduction 'MolEN (Fair, 1990)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; ZORTEP (Zsolnai, Pritzkow & Hutter, 1996) ; _computing_publication_material ; SHELXL-97. All calculations were performed on a DEC 3000 AXP and PC/486 computer. _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 w=1/[\s^2^(Fo^2^)+(0.0679P)^2^+0.2745P] 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 1(3) _refine_ls_number_reflns 1877 _refine_ls_number_parameters 220 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0946 _refine_ls_R_factor_gt 0.0509 _refine_ls_wR_factor_ref 0.1561 _refine_ls_wR_factor_gt 0.1199 _refine_ls_goodness_of_fit_ref 1.106 _refine_ls_restrained_S_all 1.106 _refine_ls_shift/su_max 0.041 _refine_ls_shift/su_mean 0.002 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O -0.0340(2) 1.0652(7) 0.0319(2) 0.0685(10) Uani 1 d . . . O2 O 0.1466(2) 0.9744(7) 0.1182(2) 0.0675(9) Uani 1 d . . . O3 O -0.0495(3) 0.5932(8) 0.2902(3) 0.0828(12) Uani 1 d . . . O4 O 0.2910(3) 0.6985(7) 0.4723(3) 0.0734(10) Uani 1 d . . . O5 O 0.5319(4) 0.8611(10) 0.5467(4) 0.1032(15) Uani 1 d . . . H5O H 0.543(6) 0.785(14) 0.487(6) 0.124 Uiso 1 d . . . N N -0.0207(2) 0.8556(7) 0.1748(2) 0.0505(9) Uani 1 d . . . C1 C -0.1476(3) 0.8973(9) 0.1392(3) 0.0527(11) Uani 1 d . . . H1 H -0.1900 0.7515 0.1348 0.079 Uiso 1 calc R . . C2 C -0.1533(4) 0.9878(13) 0.0312(3) 0.0742(16) Uani 1 d . . . H2A H -0.1772 0.8686 -0.0205 0.111 Uiso 1 calc R . . H2B H -0.2088 1.1136 0.0159 0.111 Uiso 1 calc R . . C3 C 0.0426(3) 0.9671(9) 0.1104(3) 0.0549(11) Uani 1 d . . . C4 C 0.0211(3) 0.7085(9) 0.2576(3) 0.0571(11) Uani 1 d . . . C6 C 0.1679(4) 0.6976(10) 0.4246(3) 0.0601(12) Uani 1 d . . . H6 H 0.1325 0.5581 0.4456 0.090 Uiso 1 calc R . . C5 C 0.1517(3) 0.6982(10) 0.3059(3) 0.0565(11) Uani 1 d . . . H5 H 0.1904 0.8335 0.2847 0.085 Uiso 1 calc R . . C7 C 0.1150(4) 0.9034(13) 0.4682(4) 0.0849(19) Uani 1 d . . . H7A H 0.0550 0.8559 0.5049 0.127 Uiso 1 calc R . . H7B H 0.0798 1.0078 0.4126 0.127 Uiso 1 calc R . . C8 C 0.2180(5) 1.0165(13) 0.5430(4) 0.0880(18) Uani 1 d . . . H8A H 0.2128 1.1819 0.5381 0.132 Uiso 1 calc R . . H8B H 0.2210 0.9707 0.6146 0.132 Uiso 1 calc R . . C9 C 0.3237(4) 0.9285(10) 0.5056(4) 0.0674(14) Uani 1 d . . . H9 H 0.3351 1.0195 0.4458 0.101 Uiso 1 calc R . . C10 C 0.4354(4) 0.9246(14) 0.5878(4) 0.0842(19) Uani 1 d . . . H10A H 0.4494 1.0752 0.6191 0.126 Uiso 1 calc R . . H10B H 0.4270 0.8175 0.6422 0.126 Uiso 1 calc R . . C11 C -0.1924(3) 1.0564(10) 0.2132(3) 0.0628(13) Uani 1 d . . . H11A H -0.1550 1.2047 0.2130 0.094 Uiso 1 calc R . . H11B H -0.1707 0.9954 0.2835 0.094 Uiso 1 calc R . . C12 C -0.3253(3) 1.0859(9) 0.1830(3) 0.0530(10) Uani 1 d . . . C13 C -0.3773(4) 1.2726(9) 0.1291(4) 0.0677(14) Uani 1 d . . . H13 H -0.3301 1.3844 0.1086 0.081 Uiso 1 calc R . . C14 C -0.5677(4) 1.1341(12) 0.1327(4) 0.0794(17) Uani 1 d . . . H14 H -0.6492 1.1508 0.1163 0.095 Uiso 1 calc R . . C15 C -0.4975(5) 1.2989(11) 0.1043(5) 0.0812(16) Uani 1 d . . . H15 H -0.5310 1.4283 0.0684 0.097 Uiso 1 calc R . . C16 C -0.5179(4) 0.9451(13) 0.1850(4) 0.0819(17) Uani 1 d . . . H16 H -0.5654 0.8317 0.2037 0.098 Uiso 1 calc R . . C17 C -0.3967(4) 0.9215(10) 0.2104(4) 0.0687(14) Uani 1 d . . . H17 H -0.3633 0.7924 0.2466 0.082 Uiso 1 calc R . . C18 C 0.2050(5) 0.4831(15) 0.2689(4) 0.104(3) Uani 1 d . . . H18A H 0.2880 0.4783 0.2991 0.157 Uiso 1 calc R . . H18B H 0.1929 0.4855 0.1941 0.157 Uiso 1 calc R . . H18C H 0.1677 0.3502 0.2901 0.157 Uiso 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0534(17) 0.087(3) 0.0660(18) 0.0212(19) 0.0155(13) 0.0032(18) O2 0.0465(16) 0.081(3) 0.0784(19) 0.006(2) 0.0203(13) -0.0141(18) O3 0.0588(19) 0.090(3) 0.097(2) 0.032(2) 0.0112(17) -0.018(2) O4 0.0614(19) 0.076(2) 0.073(2) -0.013(2) -0.0051(15) 0.009(2) O5 0.083(3) 0.104(4) 0.111(3) -0.016(3) -0.003(2) 0.005(3) N 0.0356(16) 0.063(2) 0.0524(18) 0.0032(19) 0.0081(13) -0.0049(17) C1 0.0345(18) 0.064(3) 0.057(2) 0.003(2) 0.0049(16) -0.0004(19) C2 0.049(2) 0.111(5) 0.062(3) 0.004(3) 0.0113(19) 0.005(3) C3 0.049(2) 0.058(3) 0.057(2) 0.002(2) 0.0120(18) -0.010(2) C4 0.047(2) 0.062(3) 0.061(2) 0.007(3) 0.0095(19) -0.003(2) C6 0.052(2) 0.068(3) 0.059(2) -0.001(3) 0.0080(19) -0.003(2) C5 0.042(2) 0.066(3) 0.059(2) 0.008(3) 0.0058(17) 0.005(2) C7 0.072(3) 0.107(5) 0.078(3) -0.021(4) 0.021(3) 0.014(3) C8 0.084(3) 0.096(5) 0.083(3) -0.022(4) 0.017(3) 0.008(3) C9 0.072(3) 0.071(4) 0.057(2) -0.005(3) 0.009(2) -0.004(3) C10 0.072(3) 0.112(6) 0.064(3) -0.010(4) 0.005(2) -0.008(4) C11 0.043(2) 0.076(4) 0.068(3) -0.015(3) 0.0092(18) 0.001(2) C12 0.046(2) 0.054(3) 0.060(2) -0.003(2) 0.0132(18) -0.002(2) C13 0.057(3) 0.055(3) 0.093(4) 0.006(3) 0.022(2) -0.004(2) C14 0.048(3) 0.092(5) 0.097(4) -0.005(4) 0.014(2) 0.009(3) C15 0.066(3) 0.073(4) 0.103(4) 0.019(3) 0.017(3) 0.022(3) C16 0.052(3) 0.086(4) 0.113(4) 0.013(4) 0.029(3) -0.008(3) C17 0.061(3) 0.067(4) 0.082(3) 0.022(3) 0.024(2) 0.000(3) C18 0.091(4) 0.136(7) 0.074(3) -0.030(4) -0.010(3) 0.047(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 O1 C3 1.335(5) . ? O1 C2 1.458(5) . ? O2 C3 1.191(4) . ? O3 C4 1.211(5) . ? O4 C6 1.432(5) . ? O4 C9 1.439(7) . ? O5 C10 1.397(7) . ? N C4 1.387(6) . ? N C3 1.398(5) . ? N C1 1.468(4) . ? C1 C2 1.500(6) . ? C1 C11 1.516(6) . ? C4 C5 1.514(5) . ? C6 C7 1.519(8) . ? C6 C5 1.526(6) . ? C5 C18 1.528(8) . ? C7 C8 1.524(8) . ? C8 C9 1.511(7) . ? C9 C10 1.497(6) . ? C11 C12 1.520(5) . ? C12 C13 1.367(7) . ? C12 C17 1.368(6) . ? C13 C15 1.373(7) . ? C14 C16 1.362(9) . ? C14 C15 1.366(8) . ? C16 C17 1.382(6) . ? 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 C3 O1 C2 110.2(4) . . ? C6 O4 C9 108.0(4) . . ? C4 N C3 128.4(3) . . ? C4 N C1 120.6(3) . . ? C3 N C1 110.8(3) . . ? N C1 C2 101.2(3) . . ? N C1 C11 111.1(3) . . ? C2 C1 C11 115.9(5) . . ? O1 C2 C1 104.9(3) . . ? O2 C3 O1 123.1(4) . . ? O2 C3 N 128.5(4) . . ? O1 C3 N 108.4(3) . . ? O3 C4 N 118.2(4) . . ? O3 C4 C5 121.7(4) . . ? N C4 C5 120.1(4) . . ? O4 C6 C7 106.3(4) . . ? O4 C6 C5 109.6(3) . . ? C7 C6 C5 114.3(4) . . ? C4 C5 C6 108.5(3) . . ? C4 C5 C18 109.8(4) . . ? C6 C5 C18 110.7(4) . . ? C6 C7 C8 105.0(4) . . ? C9 C8 C7 103.0(4) . . ? O4 C9 C10 109.5(5) . . ? O4 C9 C8 103.7(4) . . ? C10 C9 C8 114.3(4) . . ? O5 C10 C9 111.7(4) . . ? C1 C11 C12 112.1(3) . . ? C13 C12 C17 118.1(4) . . ? C13 C12 C11 122.4(4) . . ? C17 C12 C11 119.5(5) . . ? C12 C13 C15 121.6(5) . . ? C16 C14 C15 119.7(5) . . ? C14 C15 C13 119.6(5) . . ? C14 C16 C17 120.1(6) . . ? C12 C17 C16 120.8(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 C4 N C1 C2 -160.2(5) . . . . ? C3 N C1 C2 15.4(5) . . . . ? C4 N C1 C11 76.1(5) . . . . ? C3 N C1 C11 -108.3(4) . . . . ? C3 O1 C2 C1 19.8(6) . . . . ? N C1 C2 O1 -20.2(6) . . . . ? C11 C1 C2 O1 100.1(4) . . . . ? C2 O1 C3 O2 168.1(5) . . . . ? C2 O1 C3 N -10.1(5) . . . . ? C4 N C3 O2 -6.8(8) . . . . ? C1 N C3 O2 177.9(5) . . . . ? C4 N C3 O1 171.2(5) . . . . ? C1 N C3 O1 -4.0(5) . . . . ? C3 N C4 O3 -165.2(5) . . . . ? C1 N C4 O3 9.6(7) . . . . ? C3 N C4 C5 15.9(7) . . . . ? C1 N C4 C5 -169.2(4) . . . . ? C9 O4 C6 C7 -23.2(5) . . . . ? C9 O4 C6 C5 100.9(5) . . . . ? O3 C4 C5 C6 -43.4(7) . . . . ? N C4 C5 C6 135.4(5) . . . . ? O3 C4 C5 C18 77.7(6) . . . . ? N C4 C5 C18 -103.4(6) . . . . ? O4 C6 C5 C4 -177.4(4) . . . . ? C7 C6 C5 C4 -58.1(6) . . . . ? O4 C6 C5 C18 62.1(6) . . . . ? C7 C6 C5 C18 -178.7(5) . . . . ? O4 C6 C7 C8 0.0(6) . . . . ? C5 C6 C7 C8 -121.0(5) . . . . ? C6 C7 C8 C9 21.4(6) . . . . ? C6 O4 C9 C10 159.5(4) . . . . ? C6 O4 C9 C8 37.1(5) . . . . ? C7 C8 C9 O4 -35.3(6) . . . . ? C7 C8 C9 C10 -154.5(6) . . . . ? O4 C9 C10 O5 69.4(7) . . . . ? C8 C9 C10 O5 -174.8(6) . . . . ? N C1 C11 C12 -175.1(4) . . . . ? C2 C1 C11 C12 70.1(5) . . . . ? C1 C11 C12 C13 -99.7(6) . . . . ? C1 C11 C12 C17 80.4(5) . . . . ? C17 C12 C13 C15 1.3(7) . . . . ? C11 C12 C13 C15 -178.6(5) . . . . ? C16 C14 C15 C13 -0.1(9) . . . . ? C12 C13 C15 C14 -0.9(8) . . . . ? C15 C14 C16 C17 0.8(9) . . . . ? C13 C12 C17 C16 -0.6(7) . . . . ? C11 C12 C17 C16 179.3(5) . . . . ? C14 C16 C17 C12 -0.4(8) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.97 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.284 _refine_diff_density_min -0.240 _refine_diff_density_rms 0.049 #======END data_6c _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H23 N O5' _chemical_formula_weight 333.37 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 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.469(2) _cell_length_b 12.459(3) _cell_length_c 16.239(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1713.5(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10.14 _cell_measurement_theta_max 13.92 _exptl_crystal_description irregular _exptl_crystal_colour colorless _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.33 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.292 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_measurement_device_type 'Nonius CAD-4 diffractometer' _diffrn_measurement_method \w--2\q _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 0.4 _diffrn_reflns_number 1935 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0296 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 2.51 _diffrn_reflns_theta_max 25.96 _reflns_number_total 1935 _reflns_number_gt 1432 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD-4 EXPRESS (Enraf-Nonius, 1994)' _computing_cell_refinement ; SET4 in CAD-4 EXPRESS (Enraf-Nonius, 1994) ; _computing_data_reduction 'MolEN (Fair, 1990)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; ZORTEP (Zsolnai, Pritzkow & Hutter, 1996) ; _computing_publication_material ; SHELXL-97. All calculations were performed on a DEC 3000 AXP and PC/486 computer. _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 w=1/[\s^2^(Fo^2^)+(0.0572P)^2^+0.5860P] 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 SHELXL _refine_ls_extinction_coef 0.023(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 2(3) _refine_ls_number_reflns 1935 _refine_ls_number_parameters 221 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0762 _refine_ls_R_factor_gt 0.0441 _refine_ls_wR_factor_ref 0.1365 _refine_ls_wR_factor_gt 0.1112 _refine_ls_goodness_of_fit_ref 1.097 _refine_ls_restrained_S_all 1.097 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.8853(4) 0.4525(2) 0.93337(19) 0.0732(9) Uani 1 d . . . O2 O 0.7786(5) 0.5075(2) 0.81592(18) 0.0872(11) Uani 1 d . . . O3 O 0.7057(4) 0.7844(2) 0.95953(15) 0.0606(7) Uani 1 d . . . O4 O 0.4298(3) 0.7294(3) 0.83570(15) 0.0609(8) Uani 1 d . . . O5 O 0.1391(4) 0.6224(3) 0.8778(2) 0.0810(10) Uani 1 d . . . H5O H 0.216(6) 0.674(4) 0.924(3) 0.097 Uiso 1 d . . . N N 0.7788(4) 0.6149(2) 0.93334(16) 0.0445(7) Uani 1 d . . . C1 C 0.8223(4) 0.5976(3) 1.0203(2) 0.0474(9) Uani 1 d . . . H1 H 0.8863 0.6582 1.0394 0.071 Uiso 1 calc R . . C2 C 0.9271(5) 0.4987(3) 1.0119(3) 0.0658(11) Uani 1 d . . . H2A H 1.0378 0.5186 1.0129 0.099 Uiso 1 calc R . . H2B H 0.9069 0.4483 1.0562 0.099 Uiso 1 calc R . . C3 C 0.8111(6) 0.5247(3) 0.8863(3) 0.0613(11) Uani 1 d . . . C4 C 0.7284(4) 0.7155(3) 0.9074(2) 0.0451(8) Uani 1 d . . . C5 C 0.7130(4) 0.7380(3) 0.8165(2) 0.0510(9) Uani 1 d . . . H5 H 0.7233 0.6709 0.7855 0.076 Uiso 1 calc R . . C6 C 0.5539(4) 0.7896(4) 0.7975(2) 0.0531(10) Uani 1 d . . . H6 H 0.5526 0.8637 0.8178 0.080 Uiso 1 calc R . . C7 C 0.5178(6) 0.7878(5) 0.7053(3) 0.0822(16) Uani 1 d . . . H7A H 0.4674 0.8540 0.6879 0.123 Uiso 1 calc R . . H7B H 0.6131 0.7770 0.6732 0.123 Uiso 1 calc R . . C8 C 0.4057(6) 0.6926(6) 0.6969(3) 0.101(2) Uani 1 d . . . H8A H 0.3376 0.7000 0.6492 0.152 Uiso 1 calc R . . H8B H 0.4629 0.6253 0.6933 0.152 Uiso 1 calc R . . C9 C 0.3143(5) 0.7007(4) 0.7756(2) 0.0612(11) Uani 1 d . . . H9 H 0.2382 0.7596 0.7706 0.092 Uiso 1 calc R . . C10 C 0.2304(6) 0.6042(4) 0.8046(3) 0.0826(14) Uani 1 d . . . H10A H 0.1608 0.5791 0.7612 0.124 Uiso 1 calc R . . H10B H 0.3070 0.5480 0.8154 0.124 Uiso 1 calc R . . C11 C 0.6808(5) 0.5837(3) 1.0775(2) 0.0537(9) Uani 1 d . . . H11A H 0.7195 0.5758 1.1334 0.080 Uiso 1 calc R . . H11B H 0.6180 0.6488 1.0756 0.080 Uiso 1 calc R . . C12 C 0.5748(4) 0.4896(3) 1.0581(2) 0.0471(8) Uani 1 d . . . C13 C 0.4577(5) 0.4985(3) 0.9985(2) 0.0549(10) Uani 1 d . . . H13 H 0.4443 0.5630 0.9704 0.066 Uiso 1 calc R . . C14 C 0.3610(5) 0.4121(3) 0.9805(3) 0.0600(11) Uani 1 d . . . H14 H 0.2830 0.4191 0.9406 0.072 Uiso 1 calc R . . C15 C 0.3791(5) 0.3160(3) 1.0211(3) 0.0627(11) Uani 1 d . . . H15 H 0.3154 0.2575 1.0082 0.075 Uiso 1 calc R . . C16 C 0.4929(6) 0.3079(3) 1.0808(3) 0.0669(12) Uani 1 d . . . H16 H 0.5051 0.2435 1.1091 0.080 Uiso 1 calc R . . C17 C 0.5885(5) 0.3926(3) 1.0995(2) 0.0603(11) Uani 1 d . . . H17 H 0.6640 0.3852 1.1407 0.072 Uiso 1 calc R . . C18 C 0.8479(5) 0.8142(5) 0.7932(3) 0.0859(17) Uani 1 d . . . H18A H 0.8419 0.8306 0.7355 0.129 Uiso 1 calc R . . H18B H 0.9473 0.7804 0.8049 0.129 Uiso 1 calc R . . H18C H 0.8391 0.8792 0.8246 0.129 Uiso 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.094(2) 0.0435(15) 0.082(2) 0.0032(15) 0.0059(19) 0.0135(17) O2 0.138(3) 0.0609(18) 0.0626(18) -0.0147(15) -0.003(2) 0.005(2) O3 0.0804(18) 0.0487(14) 0.0525(14) -0.0049(12) -0.0002(15) 0.0120(16) O4 0.0481(14) 0.091(2) 0.0440(13) 0.0043(14) -0.0018(12) -0.0089(16) O5 0.0697(19) 0.090(2) 0.083(2) -0.0046(19) 0.0015(18) -0.015(2) N 0.0476(15) 0.0417(15) 0.0444(15) -0.0010(12) -0.0022(14) 0.0022(14) C1 0.049(2) 0.0426(18) 0.0503(19) 0.0055(15) -0.0033(17) -0.0032(17) C2 0.063(2) 0.061(2) 0.074(3) 0.014(2) -0.002(2) 0.006(2) C3 0.079(3) 0.044(2) 0.062(2) -0.0028(18) 0.005(2) 0.000(2) C4 0.0410(17) 0.0435(18) 0.0508(19) 0.0016(16) -0.0015(16) 0.0013(17) C5 0.049(2) 0.057(2) 0.0477(19) 0.0047(17) 0.0023(18) 0.0085(19) C6 0.0446(19) 0.065(2) 0.050(2) 0.0084(19) 0.0051(17) 0.004(2) C7 0.057(3) 0.134(4) 0.056(2) 0.032(3) 0.000(2) 0.015(3) C8 0.076(3) 0.178(6) 0.050(2) -0.015(3) -0.007(2) 0.002(4) C9 0.048(2) 0.083(3) 0.053(2) -0.009(2) -0.0041(19) 0.003(2) C10 0.073(3) 0.091(3) 0.084(3) -0.018(3) -0.013(3) -0.003(3) C11 0.067(2) 0.048(2) 0.0461(18) -0.0013(16) -0.0015(19) -0.005(2) C12 0.050(2) 0.0475(19) 0.0436(17) 0.0003(16) 0.0028(17) 0.0018(18) C13 0.058(2) 0.054(2) 0.054(2) 0.004(2) 0.0052(19) 0.005(2) C14 0.050(2) 0.072(3) 0.058(2) -0.007(2) -0.0005(19) 0.001(2) C15 0.061(2) 0.062(3) 0.064(2) -0.006(2) 0.013(2) -0.011(2) C16 0.077(3) 0.049(2) 0.075(3) 0.013(2) 0.002(2) -0.010(2) C17 0.061(2) 0.063(2) 0.058(2) 0.0166(19) -0.004(2) 0.000(2) C18 0.046(2) 0.139(5) 0.073(3) 0.026(3) 0.004(2) -0.008(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C3 1.337(5) . ? O1 C2 1.443(5) . ? O2 C3 1.195(5) . ? O3 C4 1.220(4) . ? O4 C9 1.427(5) . ? O4 C6 1.432(5) . ? O5 C10 1.437(6) . ? N C3 1.386(5) . ? N C4 1.388(4) . ? N C1 1.475(4) . ? C1 C2 1.525(5) . ? C1 C11 1.526(5) . ? C4 C5 1.510(5) . ? C5 C6 1.523(5) . ? C5 C18 1.532(6) . ? C6 C7 1.530(5) . ? C7 C8 1.525(8) . ? C8 C9 1.498(6) . ? C9 C10 1.473(7) . ? C11 C12 1.511(5) . ? C12 C17 1.388(5) . ? C12 C13 1.391(5) . ? C13 C14 1.383(6) . ? C14 C15 1.375(6) . ? C15 C16 1.371(6) . ? C16 C17 1.364(6) . ? 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 C3 O1 C2 110.6(3) . . ? C9 O4 C6 109.8(3) . . ? C3 N C4 128.7(3) . . ? C3 N C1 111.1(3) . . ? C4 N C1 119.9(3) . . ? N C1 C2 100.3(3) . . ? N C1 C11 113.8(3) . . ? C2 C1 C11 114.8(3) . . ? O1 C2 C1 105.0(3) . . ? O2 C3 O1 122.3(4) . . ? O2 C3 N 128.8(4) . . ? O1 C3 N 108.9(3) . . ? O3 C4 N 118.2(3) . . ? O3 C4 C5 122.3(3) . . ? N C4 C5 119.4(3) . . ? C4 C5 C6 110.6(3) . . ? C4 C5 C18 107.0(3) . . ? C6 C5 C18 110.4(3) . . ? O4 C6 C5 110.0(3) . . ? O4 C6 C7 105.6(3) . . ? C5 C6 C7 111.6(3) . . ? C8 C7 C6 102.9(4) . . ? C9 C8 C7 101.1(4) . . ? O4 C9 C10 108.4(4) . . ? O4 C9 C8 104.3(3) . . ? C10 C9 C8 117.8(4) . . ? O5 C10 C9 113.3(4) . . ? C12 C11 C1 115.3(3) . . ? C17 C12 C13 117.8(4) . . ? C17 C12 C11 121.7(3) . . ? C13 C12 C11 120.4(3) . . ? C14 C13 C12 120.4(4) . . ? C15 C14 C13 120.7(4) . . ? C16 C15 C14 118.7(4) . . ? C17 C16 C15 121.2(4) . . ? C16 C17 C12 121.1(4) . . ? 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 N C1 C2 15.8(4) . . . . ? C4 N C1 C2 -158.2(3) . . . . ? C3 N C1 C11 -107.3(4) . . . . ? C4 N C1 C11 78.7(4) . . . . ? C3 O1 C2 C1 18.6(4) . . . . ? N C1 C2 O1 -19.7(4) . . . . ? C11 C1 C2 O1 102.6(4) . . . . ? C2 O1 C3 O2 172.9(5) . . . . ? C2 O1 C3 N -8.7(5) . . . . ? C4 N C3 O2 -13.8(8) . . . . ? C1 N C3 O2 172.9(5) . . . . ? C4 N C3 O1 167.9(3) . . . . ? C1 N C3 O1 -5.4(5) . . . . ? C3 N C4 O3 179.6(4) . . . . ? C1 N C4 O3 -7.6(5) . . . . ? C3 N C4 C5 -4.0(6) . . . . ? C1 N C4 C5 168.8(3) . . . . ? O3 C4 C5 C6 -52.3(5) . . . . ? N C4 C5 C6 131.4(4) . . . . ? O3 C4 C5 C18 68.0(5) . . . . ? N C4 C5 C18 -108.2(4) . . . . ? C9 O4 C6 C5 -126.2(4) . . . . ? C9 O4 C6 C7 -5.6(5) . . . . ? C4 C5 C6 O4 -49.0(4) . . . . ? C18 C5 C6 O4 -167.2(4) . . . . ? C4 C5 C6 C7 -165.9(4) . . . . ? C18 C5 C6 C7 75.9(5) . . . . ? O4 C6 C7 C8 -19.4(5) . . . . ? C5 C6 C7 C8 100.1(4) . . . . ? C6 C7 C8 C9 35.7(5) . . . . ? C6 O4 C9 C10 155.5(4) . . . . ? C6 O4 C9 C8 29.1(5) . . . . ? C7 C8 C9 O4 -39.9(5) . . . . ? C7 C8 C9 C10 -160.1(4) . . . . ? O4 C9 C10 O5 65.5(5) . . . . ? C8 C9 C10 O5 -176.5(4) . . . . ? N C1 C11 C12 60.5(4) . . . . ? C2 C1 C11 C12 -54.2(4) . . . . ? C1 C11 C12 C17 97.7(4) . . . . ? C1 C11 C12 C13 -83.3(4) . . . . ? C17 C12 C13 C14 -1.3(5) . . . . ? C11 C12 C13 C14 179.7(3) . . . . ? C12 C13 C14 C15 -0.2(6) . . . . ? C13 C14 C15 C16 1.3(6) . . . . ? C14 C15 C16 C17 -0.9(7) . . . . ? C15 C16 C17 C12 -0.6(7) . . . . ? C13 C12 C17 C16 1.7(6) . . . . ? C11 C12 C17 C16 -179.4(4) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.96 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.235 _refine_diff_density_min -0.159 _refine_diff_density_rms 0.039 #======END data_5b _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H23 N O5' _chemical_formula_weight 333.37 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 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.465(2) _cell_length_b 12.419(3) _cell_length_c 15.796(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1660.6(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10.45 _cell_measurement_theta_max 13.21 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.33 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.333 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Nonius CAD-4 diffractometer' _diffrn_measurement_method \w--2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 0.2 _diffrn_reflns_number 1687 _diffrn_reflns_av_R_equivalents 0.0046 _diffrn_reflns_av_sigmaI/netI 0.0429 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.73 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1686 _reflns_number_gt 1200 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD-4 EXPRESS (Enraf-Nonius, 1994)' _computing_cell_refinement ; SET4 in CAD-4 EXPRESS (Enraf-Nonius, 1994) ; _computing_data_reduction 'MolEN (Fair, 1990)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; ZORTEP (Zsolnai, Pritzkow & Hutter, 1996) ; _computing_publication_material ; SHELXL-97. All calculations were performed on a DEC 3000 AXP and PC/486 computer. _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 w=1/[\s^2^(Fo^2^)+(0.1007P)^2^+1.4755P] 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 SHELXL _refine_ls_extinction_coef 0.024(6) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 2(4) _refine_ls_number_reflns 1686 _refine_ls_number_parameters 221 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1078 _refine_ls_R_factor_gt 0.0614 _refine_ls_wR_factor_ref 0.2083 _refine_ls_wR_factor_gt 0.1538 _refine_ls_goodness_of_fit_ref 1.163 _refine_ls_restrained_S_all 1.163 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.6366(6) 0.5457(3) 0.5723(3) 0.0530(14) Uani 1 d . . . O2 O 0.7490(8) 0.4885(4) 0.6911(3) 0.0656(16) Uani 1 d . . . O3 O 0.8061(6) 0.2117(3) 0.5406(3) 0.0502(13) Uani 1 d . . . O4 O 1.0823(5) 0.3039(4) 0.6548(3) 0.0459(12) Uani 1 d . . . O5 O 1.3931(7) 0.3721(5) 0.6229(3) 0.0658(17) Uani 1 d . . . H5O H 1.340(12) 0.336(7) 0.596(6) 0.079 Uiso 1 d . . . N N 0.7429(6) 0.3826(4) 0.5686(3) 0.0340(12) Uani 1 d . . . C1 C 0.6980(8) 0.4022(5) 0.4806(4) 0.0398(15) Uani 1 d . . . H1 H 0.6334 0.3419 0.4605 0.060 Uiso 1 calc R . . C2 C 0.5928(9) 0.5005(5) 0.4917(5) 0.0514(19) Uani 1 d . . . H2A H 0.6107 0.5520 0.4465 0.077 Uiso 1 calc R . . H2B H 0.4823 0.4800 0.4915 0.077 Uiso 1 calc R . . C3 C 0.7119(9) 0.4719(5) 0.6186(4) 0.0439(16) Uani 1 d . . . C4 C 0.7887(7) 0.2810(4) 0.5936(4) 0.0351(14) Uani 1 d . . . C5 C 0.8100(8) 0.2557(5) 0.6870(4) 0.0386(15) Uani 1 d . . . H5 H 0.7801 0.3188 0.7207 0.058 Uiso 1 calc R . . C6 C 0.9869(8) 0.2305(6) 0.7016(4) 0.0442(17) Uani 1 d . . . H6 H 1.0096 0.1567 0.6834 0.066 Uiso 1 calc R . . C7 C 1.0376(10) 0.2450(7) 0.7938(4) 0.061(2) Uani 1 d . . . H7A H 0.9504 0.2312 0.8321 0.092 Uiso 1 calc R . . H7B H 1.1247 0.1975 0.8079 0.092 Uiso 1 calc R . . C8 C 1.0880(10) 0.3621(6) 0.7973(5) 0.062(2) Uani 1 d . . . H8A H 1.1667 0.3737 0.8410 0.093 Uiso 1 calc R . . H8B H 0.9984 0.4089 0.8076 0.093 Uiso 1 calc R . . C9 C 1.1573(8) 0.3810(6) 0.7091(4) 0.0459(16) Uani 1 d . . . H9 H 1.1324 0.4542 0.6900 0.069 Uiso 1 calc R . . C10 C 1.3318(9) 0.3633(6) 0.7063(4) 0.056(2) Uani 1 d . . . H10A H 1.3834 0.4158 0.7423 0.084 Uiso 1 calc R . . H10B H 1.3556 0.2922 0.7284 0.084 Uiso 1 calc R . . C11 C 0.8367(9) 0.4183(5) 0.4198(4) 0.0451(17) Uani 1 d . . . H11A H 0.9012 0.3538 0.4201 0.068 Uiso 1 calc R . . H11B H 0.7954 0.4272 0.3629 0.068 Uiso 1 calc R . . C12 C 0.9408(8) 0.5142(5) 0.4405(4) 0.0374(15) Uani 1 d . . . C13 C 0.9166(8) 0.6123(5) 0.4000(4) 0.0424(15) Uani 1 d . . . H13 H 0.8366 0.6193 0.3600 0.051 Uiso 1 calc R . . C14 C 1.0118(9) 0.6994(5) 0.4193(5) 0.0501(18) Uani 1 d . . . H14 H 0.9948 0.7650 0.3923 0.060 Uiso 1 calc R . . C15 C 1.1307(9) 0.6905(5) 0.4776(4) 0.0533(19) Uani 1 d . . . H15 H 1.1935 0.7497 0.4905 0.064 Uiso 1 calc R . . C16 C 1.1568(9) 0.5927(5) 0.5173(4) 0.0485(17) Uani 1 d . . . H16 H 1.2384 0.5857 0.5563 0.058 Uiso 1 calc R . . C17 C 1.0620(8) 0.5059(5) 0.4991(4) 0.0436(16) Uani 1 d . . . H17 H 1.0794 0.4407 0.5264 0.052 Uiso 1 calc R . . C18 C 0.7069(10) 0.1610(6) 0.7121(5) 0.062(2) Uani 1 d . . . H18A H 0.7213 0.1458 0.7712 0.094 Uiso 1 calc R . . H18B H 0.7361 0.0990 0.6794 0.094 Uiso 1 calc R . . H18C H 0.5981 0.1783 0.7016 0.094 Uiso 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.074(4) 0.031(2) 0.054(3) 0.006(2) -0.003(3) 0.012(2) O2 0.109(5) 0.040(3) 0.047(3) -0.008(2) -0.011(3) 0.003(3) O3 0.075(3) 0.033(2) 0.042(2) -0.004(2) 0.002(2) 0.006(3) O4 0.050(3) 0.051(3) 0.037(2) 0.000(2) 0.002(2) -0.009(2) O5 0.065(4) 0.087(4) 0.046(3) -0.009(3) 0.001(3) -0.027(3) N 0.042(3) 0.030(2) 0.031(3) 0.000(2) -0.002(2) 0.003(2) C1 0.045(4) 0.038(3) 0.037(3) 0.004(3) -0.007(3) -0.004(3) C2 0.052(4) 0.049(4) 0.054(4) 0.012(3) -0.004(4) 0.001(4) C3 0.054(4) 0.031(3) 0.047(4) 0.002(3) 0.000(3) -0.001(3) C4 0.043(3) 0.029(3) 0.034(3) 0.004(3) 0.004(3) 0.001(3) C5 0.043(3) 0.033(3) 0.040(3) 0.008(3) 0.004(3) 0.008(3) C6 0.056(4) 0.044(4) 0.033(3) 0.006(3) 0.006(3) 0.004(3) C7 0.060(5) 0.081(5) 0.042(4) 0.018(4) 0.001(4) 0.003(4) C8 0.063(5) 0.080(5) 0.043(4) -0.009(4) 0.001(4) 0.005(5) C9 0.049(4) 0.052(4) 0.037(4) -0.004(3) -0.009(3) 0.004(4) C10 0.055(4) 0.065(5) 0.048(4) -0.005(4) 0.000(4) -0.004(4) C11 0.062(4) 0.036(3) 0.037(3) -0.001(3) 0.000(3) -0.002(3) C12 0.044(4) 0.037(3) 0.031(3) 0.000(3) 0.003(3) 0.002(3) C13 0.044(3) 0.046(4) 0.037(3) 0.011(3) -0.001(3) -0.002(3) C14 0.057(4) 0.042(4) 0.052(4) 0.007(3) 0.010(4) 0.002(4) C15 0.064(5) 0.042(4) 0.054(4) -0.010(3) 0.011(4) -0.012(4) C16 0.049(4) 0.057(4) 0.039(4) -0.006(3) -0.005(3) -0.001(4) C17 0.052(4) 0.038(4) 0.040(3) 0.002(3) 0.006(3) 0.003(3) C18 0.060(5) 0.067(5) 0.060(5) 0.025(4) 0.004(4) -0.008(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 O1 C3 1.334(8) . ? O1 C2 1.440(8) . ? O2 C3 1.205(8) . ? O3 C4 1.209(7) . ? O4 C6 1.425(8) . ? O4 C9 1.433(8) . ? O5 C10 1.420(9) . ? N C4 1.378(7) . ? N C3 1.387(8) . ? N C1 1.462(7) . ? C1 C2 1.521(9) . ? C1 C11 1.530(10) . ? C4 C5 1.519(8) . ? C5 C18 1.517(9) . ? C5 C6 1.547(10) . ? C6 C7 1.528(9) . ? C7 C8 1.517(11) . ? C8 C9 1.530(10) . ? C9 C10 1.494(10) . ? C11 C12 1.518(9) . ? C12 C17 1.384(9) . ? C12 C13 1.391(8) . ? C13 C14 1.383(9) . ? C14 C15 1.369(10) . ? C15 C16 1.384(9) . ? C16 C17 1.374(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 C3 O1 C2 109.9(5) . . ? C6 O4 C9 111.6(5) . . ? C4 N C3 128.5(5) . . ? C4 N C1 119.9(5) . . ? C3 N C1 111.0(5) . . ? N C1 C2 100.2(5) . . ? N C1 C11 114.8(6) . . ? C2 C1 C11 114.6(5) . . ? O1 C2 C1 105.3(5) . . ? O2 C3 O1 121.9(6) . . ? O2 C3 N 128.9(6) . . ? O1 C3 N 109.1(5) . . ? O3 C4 N 119.1(5) . . ? O3 C4 C5 120.7(5) . . ? N C4 C5 120.1(5) . . ? C18 C5 C4 110.3(6) . . ? C18 C5 C6 111.2(5) . . ? C4 C5 C6 107.5(5) . . ? O4 C6 C7 105.1(6) . . ? O4 C6 C5 110.0(5) . . ? C7 C6 C5 113.0(6) . . ? C8 C7 C6 103.1(6) . . ? C7 C8 C9 102.8(6) . . ? O4 C9 C10 108.8(6) . . ? O4 C9 C8 105.8(6) . . ? C10 C9 C8 112.6(6) . . ? O5 C10 C9 112.2(6) . . ? C12 C11 C1 114.4(5) . . ? C17 C12 C13 118.8(6) . . ? C17 C12 C11 121.1(6) . . ? C13 C12 C11 120.1(6) . . ? C14 C13 C12 119.8(6) . . ? C15 C14 C13 120.9(6) . . ? C14 C15 C16 119.5(7) . . ? C17 C16 C15 120.0(7) . . ? C16 C17 C12 121.0(6) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.340 _refine_diff_density_min -0.401 _refine_diff_density_rms 0.082 #======END data_5e _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H20 Br N O5' _chemical_formula_weight 398.25 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' 'Br' 'Br' -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.4983(17) _cell_length_b 12.520(3) _cell_length_c 15.821(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1683.4(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10.38 _cell_measurement_theta_max 18.29 _exptl_crystal_description irregular _exptl_crystal_colour colorless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.571 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 2.469 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.9981 _exptl_absorpt_correction_T_max 0.8564 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Nonius CAD-4 diffractometer' _diffrn_measurement_method \w--2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 0.7 _diffrn_reflns_number 1961 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0676 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.57 _diffrn_reflns_theta_max 26.27 _reflns_number_total 1961 _reflns_number_gt 1300 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD-4 EXPRESS (Enraf-Nonius, 1994)' _computing_cell_refinement ; SET4 in CAD-4 EXPRESS (Enraf-Nonius, 1994) ; _computing_data_reduction 'MolEN (Fair, 1990)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; ZORTEP (Zsolnai, Pritzkow & Hutter, 1996) ; _computing_publication_material ; SHELXL-97. All calculations were performed on a DEC 3000 AXP and PC/486 computer. _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 w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+2.0448P] 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 SHELXL _refine_ls_extinction_coef 0.0124(6) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.02(2) _refine_ls_number_reflns 1961 _refine_ls_number_parameters 221 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1076 _refine_ls_R_factor_gt 0.0382 _refine_ls_wR_factor_ref 0.0838 _refine_ls_wR_factor_gt 0.0569 _refine_ls_goodness_of_fit_ref 1.205 _refine_ls_restrained_S_all 1.205 _refine_ls_shift/su_max 0.014 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.17995(10) 0.65136(6) 0.72459(5) 0.0576(3) Uani 1 d . . . O1 O 0.8981(6) 0.8709(5) 0.6226(3) 0.0579(17) Uani 1 d . . . H1O H 0.848(10) 0.850(7) 0.589(5) 0.069 Uiso 1 d . . . O2 O 0.5875(6) 0.8026(4) 0.6546(3) 0.0436(13) Uani 1 d . . . O3 O 0.3118(7) 0.7146(3) 0.5422(3) 0.0444(12) Uani 1 d . . . O4 O 0.2429(7) 0.9882(4) 0.6910(3) 0.0580(16) Uani 1 d . . . O5 O 0.1352(6) 1.0458(4) 0.5713(3) 0.0493(14) Uani 1 d . . . N N 0.2446(6) 0.8846(4) 0.5689(3) 0.0292(13) Uani 1 d . . . C1 C 0.6648(8) 0.8780(5) 0.7108(4) 0.0430(17) Uani 1 d . . . H1 H 0.6410 0.9512 0.6928 0.052 Uiso 1 calc R . . C2 C 0.5959(9) 0.8582(7) 0.7972(4) 0.058(2) Uani 1 d . . . H2A H 0.5074 0.9052 0.8078 0.070 Uiso 1 calc R . . H2B H 0.6743 0.8689 0.8410 0.070 Uiso 1 calc R . . C3 C 0.5436(9) 0.7426(7) 0.7939(4) 0.055(2) Uani 1 d . . . H3A H 0.4570 0.7294 0.8324 0.066 Uiso 1 calc R . . H3B H 0.6296 0.6946 0.8073 0.066 Uiso 1 calc R . . C4 C 0.4920(8) 0.7306(5) 0.7020(4) 0.0385(18) Uani 1 d . . . H4 H 0.5085 0.6571 0.6827 0.046 Uiso 1 calc R . . C5 C 0.3199(8) 0.7643(5) 0.6877(4) 0.0335(15) Uani 1 d . . . H5 H 0.2977 0.8296 0.7197 0.040 Uiso 1 calc R . . C6 C 0.2920(8) 0.7841(5) 0.5949(4) 0.0343(17) Uani 1 d . . . C7 C 0.2108(9) 0.9733(6) 0.6189(5) 0.045(2) Uani 1 d . . . C8 C 0.0936(9) 1.0007(6) 0.4906(5) 0.049(2) Uani 1 d . . . H8A H 0.1129 1.0516 0.4455 0.059 Uiso 1 calc R . . H8B H -0.0166 0.9806 0.4896 0.059 Uiso 1 calc R . . C9 C 0.1979(8) 0.9031(5) 0.4806(4) 0.0339(16) Uani 1 d . . . H9 H 0.1348 0.8427 0.4605 0.041 Uiso 1 calc R . . C10 C 0.3389(9) 0.9198(5) 0.4218(4) 0.0393(17) Uani 1 d . . . H10A H 0.4033 0.8558 0.4232 0.047 Uiso 1 calc R . . H10B H 0.3001 0.9280 0.3645 0.047 Uiso 1 calc R . . C11 C 0.4405(8) 1.0132(5) 0.4422(4) 0.0316(16) Uani 1 d . . . C12 C 0.5614(8) 1.0051(6) 0.5012(5) 0.0404(18) Uani 1 d . . . H12 H 0.5788 0.9400 0.5278 0.049 Uiso 1 calc R . . C13 C 0.6559(10) 1.0909(6) 0.5213(4) 0.046(2) Uani 1 d . . . H13 H 0.7368 1.0828 0.5604 0.055 Uiso 1 calc R . . C14 C 0.6311(9) 1.1882(6) 0.4837(5) 0.049(2) Uani 1 d . . . H14 H 0.6919 1.2471 0.4984 0.058 Uiso 1 calc R . . C15 C 0.5147(9) 1.1970(5) 0.4239(5) 0.048(2) Uani 1 d . . . H15 H 0.5001 1.2620 0.3966 0.058 Uiso 1 calc R . . C16 C 0.4191(9) 1.1121(5) 0.4034(4) 0.0424(19) Uani 1 d . . . H16 H 0.3398 1.1207 0.3635 0.051 Uiso 1 calc R . . C17 C 0.8386(8) 0.8590(6) 0.7054(4) 0.0478(18) Uani 1 d . . . H17A H 0.8921 0.9089 0.7425 0.057 Uiso 1 calc R . . H17B H 0.8614 0.7874 0.7252 0.057 Uiso 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 Br1 0.0491(4) 0.0617(5) 0.0619(5) 0.0236(5) 0.0040(5) -0.0074(5) O1 0.045(3) 0.082(5) 0.047(4) 0.000(3) 0.004(3) -0.015(3) O2 0.046(3) 0.054(3) 0.030(3) -0.002(2) 0.003(2) -0.010(3) O3 0.060(3) 0.037(3) 0.037(2) -0.007(2) -0.001(3) 0.005(3) O4 0.099(4) 0.035(3) 0.040(3) -0.007(2) -0.003(3) 0.014(3) O5 0.061(4) 0.037(3) 0.050(3) 0.006(3) -0.002(3) 0.012(3) N 0.030(3) 0.028(3) 0.030(3) 0.003(2) -0.004(2) 0.005(2) C1 0.044(4) 0.046(4) 0.039(4) -0.011(3) -0.005(4) 0.000(4) C2 0.046(4) 0.099(7) 0.029(4) -0.016(5) -0.004(3) 0.008(5) C3 0.047(5) 0.088(6) 0.031(5) 0.021(4) 0.003(4) 0.003(5) C4 0.042(4) 0.035(4) 0.039(4) 0.011(3) 0.009(3) 0.008(3) C5 0.040(4) 0.032(3) 0.028(3) 0.004(3) 0.002(4) 0.005(4) C6 0.035(4) 0.034(4) 0.035(4) 0.002(3) 0.002(3) -0.012(3) C7 0.053(5) 0.038(4) 0.043(4) 0.003(4) 0.005(4) 0.002(4) C8 0.051(5) 0.050(5) 0.047(5) 0.012(4) -0.004(5) 0.002(4) C9 0.034(4) 0.033(4) 0.035(4) 0.006(3) -0.002(4) -0.002(3) C10 0.055(5) 0.030(3) 0.032(4) 0.004(3) 0.003(4) 0.008(4) C11 0.035(4) 0.032(4) 0.028(4) -0.002(3) 0.001(3) -0.001(3) C12 0.048(4) 0.035(4) 0.038(4) 0.005(4) 0.003(4) 0.005(4) C13 0.044(5) 0.055(5) 0.038(4) -0.001(4) -0.005(4) 0.001(5) C14 0.048(5) 0.048(5) 0.050(5) -0.010(4) 0.008(4) -0.011(4) C15 0.052(5) 0.030(4) 0.062(5) 0.009(4) 0.010(5) 0.010(4) C16 0.049(5) 0.039(4) 0.039(4) 0.008(3) -0.003(4) -0.009(4) C17 0.038(4) 0.063(5) 0.043(4) 0.000(4) -0.001(4) 0.000(5) _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 Br1 C5 1.938(7) . ? O1 C17 1.412(8) . ? O2 C4 1.426(7) . ? O2 C1 1.453(7) . ? O3 C6 1.217(7) . ? O4 C7 1.187(8) . ? O5 C7 1.343(8) . ? O5 C8 1.440(8) . ? N C6 1.384(7) . ? N C7 1.393(8) . ? N C9 1.470(7) . ? C1 C17 1.498(9) . ? C1 C2 1.508(9) . ? C2 C3 1.515(10) . ? C3 C4 1.526(9) . ? C4 C5 1.538(9) . ? C5 C6 1.507(8) . ? C8 C9 1.518(9) . ? C9 C10 1.531(9) . ? C10 C11 1.490(9) . ? C11 C12 1.391(9) . ? C11 C16 1.393(9) . ? C12 C13 1.378(10) . ? C13 C14 1.373(9) . ? C14 C15 1.372(10) . ? C15 C16 1.378(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 C4 O2 C1 110.3(5) . . ? C7 O5 C8 110.5(5) . . ? C6 N C7 128.0(6) . . ? C6 N C9 120.3(5) . . ? C7 N C9 111.0(5) . . ? O2 C1 C17 107.9(6) . . ? O2 C1 C2 105.8(5) . . ? C17 C1 C2 114.1(6) . . ? C1 C2 C3 103.9(6) . . ? C2 C3 C4 102.2(6) . . ? O2 C4 C3 105.9(6) . . ? O2 C4 C5 106.9(5) . . ? C3 C4 C5 112.7(6) . . ? C6 C5 C4 109.7(6) . . ? C6 C5 Br1 108.4(5) . . ? C4 C5 Br1 109.8(4) . . ? O3 C6 N 119.1(6) . . ? O3 C6 C5 121.9(6) . . ? N C6 C5 119.0(6) . . ? O4 C7 O5 122.9(7) . . ? O4 C7 N 128.5(7) . . ? O5 C7 N 108.6(6) . . ? O5 C8 C9 105.3(6) . . ? N C9 C8 100.7(5) . . ? N C9 C10 112.8(6) . . ? C8 C9 C10 114.2(5) . . ? C11 C10 C9 115.4(5) . . ? C12 C11 C16 117.2(7) . . ? C12 C11 C10 121.1(6) . . ? C16 C11 C10 121.7(6) . . ? C13 C12 C11 121.9(7) . . ? C14 C13 C12 120.1(7) . . ? C15 C14 C13 118.8(7) . . ? C14 C15 C16 121.7(7) . . ? C15 C16 C11 120.3(7) . . ? O1 C17 C1 112.9(6) . . ? 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 O2 C1 C17 115.5(6) . . . . ? C4 O2 C1 C2 -7.0(7) . . . . ? O2 C1 C2 C3 26.0(7) . . . . ? C17 C1 C2 C3 -92.4(7) . . . . ? C1 C2 C3 C4 -34.0(7) . . . . ? C1 O2 C4 C3 -14.9(7) . . . . ? C1 O2 C4 C5 105.6(6) . . . . ? C2 C3 C4 O2 30.4(7) . . . . ? C2 C3 C4 C5 -86.2(7) . . . . ? O2 C4 C5 C6 46.2(7) . . . . ? C3 C4 C5 C6 162.2(6) . . . . ? O2 C4 C5 Br1 165.3(4) . . . . ? C3 C4 C5 Br1 -78.7(6) . . . . ? C7 N C6 O3 177.7(7) . . . . ? C9 N C6 O3 8.4(10) . . . . ? C7 N C6 C5 -3.2(10) . . . . ? C9 N C6 C5 -172.5(6) . . . . ? C4 C5 C6 O3 59.5(9) . . . . ? Br1 C5 C6 O3 -60.4(8) . . . . ? C4 C5 C6 N -119.5(6) . . . . ? Br1 C5 C6 N 120.5(5) . . . . ? C8 O5 C7 O4 -172.2(8) . . . . ? C8 O5 C7 N 9.2(8) . . . . ? C6 N C7 O4 15.7(13) . . . . ? C9 N C7 O4 -174.2(8) . . . . ? C6 N C7 O5 -165.9(6) . . . . ? C9 N C7 O5 4.2(8) . . . . ? C7 O5 C8 C9 -18.4(8) . . . . ? C6 N C9 C8 156.4(6) . . . . ? C7 N C9 C8 -14.6(7) . . . . ? C6 N C9 C10 -81.5(7) . . . . ? C7 N C9 C10 107.5(6) . . . . ? O5 C8 C9 N 19.0(7) . . . . ? O5 C8 C9 C10 -102.1(7) . . . . ? N C9 C10 C11 -60.9(7) . . . . ? C8 C9 C10 C11 53.3(8) . . . . ? C9 C10 C11 C12 85.5(8) . . . . ? C9 C10 C11 C16 -94.5(7) . . . . ? C16 C11 C12 C13 0.4(10) . . . . ? C10 C11 C12 C13 -179.6(6) . . . . ? C11 C12 C13 C14 0.9(11) . . . . ? C12 C13 C14 C15 -2.3(11) . . . . ? C13 C14 C15 C16 2.6(11) . . . . ? C14 C15 C16 C11 -1.3(11) . . . . ? C12 C11 C16 C15 -0.2(10) . . . . ? C10 C11 C16 C15 179.8(6) . . . . ? O2 C1 C17 O1 58.6(8) . . . . ? C2 C1 C17 O1 175.8(6) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.27 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.463 _refine_diff_density_min -0.414 _refine_diff_density_rms 0.099 #======END