# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2001 data_global #============================================================================== _audit_creation_date '1999-11-10' _audit_creation_method 'by teXsan for Windows v1.0' _audit_update_record ? _journal_coden_Cambridge 207 loop_ _publ_author_name 'Elliott, Christine E.' 'Burnell, D. Jean' 'Miller, David O.' #============================================================================== # SUBMISSION DETAILS _publ_requested_journal ' Perkin Transactions 1' _publ_contact_author_name 'Dr D. Jean Burnell' _publ_contact_author_address ; Prof D J Burnell Department of Chemistry Memorial University of Newfoundland St. John's, Newfoundland Canada A1B 3X7 ; _publ_contact_author_phone '709 737 8535' _publ_contact_author_fax '709 737 3702' _publ_contact_author_email 'jburnell@mun.ca' #============================================================================== # TITLE AND AUTHOR LIST _publ_section_title ; Synthesis of 6-alkyl anaolgues of the 1-azabicyclo[4.3.0]nonan-2-one system by a strategy of geminal acylation and Beckmann rearrangement ; #============================================================================== # TEXT _publ_section_references ; ENTER OTHER REFERENCES Molecular Structure Corporation. (1997-1999). teXsan for Windows. Single Crystal Structure Analysis Software. Version 1.06. MSC, 9009 New Trails Drive, The Woodlands, TX 77381, USA. North, A.C.T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359. Altomare, A., Cascarano, M., Giacovazzo, C., Guagliardi, A. (1994). J. Appl. Cryst., 26, 343. Zachariasen, W. H. (1967). Acta Cryst. 23, 558-564. Sheldrick, G.M. (1997). ; #============================================================================== data__cee20c-3_________________ _database_code_CSD 171040 #============================================================================== _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan for Windows version 1.06 (MSC, 1997-1999)' _computing_structure_solution 'SHELX97 (Sheldrick, 1997)' _computing_structure_refinement 'teXsan for Windows version 1.06 (MSC, 1997-1999)' _computing_publication_material 'teXsan for Windows version 1.06 (MSC, 1997-1999)' #------------------------------------------------------------------------------ _cell_length_a 10.807(1) _cell_length_b 12.290(2) _cell_length_c 6.044(1) _cell_angle_alpha 102.16(1) _cell_angle_beta 90.42(1) _cell_angle_gamma 99.49(1) _cell_volume 773.3(2) _cell_formula_units_Z 2 _cell_measurement_temperature 299.2 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 29.1 _cell_measurement_theta_max 30.0 #------------------------------------------------------------------------------ _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_Int_Tables_number 2 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' ' -x, -y, -z' #------------------------------------------------------------------------------ _publ_section_exptl_prep ; ENTER EXPERIMENTAL SECTION ; _exptl_crystal_description 'prism' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_diffrn 1.140 _exptl_crystal_density_meas 'not measured' _chemical_formula_weight 265.39 _chemical_formula_analytical ? _chemical_formula_sum 'C16 H27 N O2 ' _chemical_formula_moiety 'C16 H27 N O2 ' _chemical_formula_structural ? _chemical_compound_source ? _exptl_crystal_F_000 292.00 _exptl_absorpt_coefficient_mu 0.580 _exptl_absorpt_correction_type ; \y scans (North,Phillips & Matthews, 1968) ; _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.904 _exptl_special_details ; The scan width was (1.73+0.14tan\q)\% with an \w scan speed of 4\% per minute (up to 6 scans to achieve I/\s(I) > 10). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1. ; #============================================================================== # EXPERIMENTAL DATA _diffrn_special_details ; ? ; _diffrn_ambient_temperature 299.2 _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device 'Rigaku AFC6S' _diffrn_measurement_method \w-2\q _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% 0.08 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -2 2 -1 -2 3 -1 -1 4 -1 _diffrn_reflns_number 2433 _reflns_number_total 2293 _reflns_number_gt 1871 _reflns_threshold_expression I>2.00\s(I) _diffrn_reflns_av_R_equivalents 0.01560 _diffrn_reflns_av_sigmaI/netI 0.026 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 3.73 _diffrn_reflns_theta_max 60.08 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 -0.04835 _diffrn_orient_matrix_UB_12 0.06395 _diffrn_orient_matrix_UB_13 0.02574 _diffrn_orient_matrix_UB_21 0.08049 _diffrn_orient_matrix_UB_22 0.05516 _diffrn_orient_matrix_UB_23 0.02098 _diffrn_orient_matrix_UB_31 -0.00150 _diffrn_orient_matrix_UB_32 -0.00163 _diffrn_orient_matrix_UB_33 -0.16611 #------------------------------------------------------------------------------ loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 32 0.017 0.009 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; H 0 54 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; O 0 4 0.047 0.032 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; N 0 2 0.029 0.018 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_refinement_flags _atom_site_adp_type _atom_site_calc_flag _atom_site_calc_attached_atom O(1) 0.06307(7) 0.13258(6) 0.4616(1) 0.0637(3) 1.000 . Uani d ? O(2) 0.39110(8) 0.16089(7) 1.1421(1) 0.0696(3) 1.000 . Uani d ? N(1) 0.15234(8) 0.04870(8) 0.7034(2) 0.0448(3) 1.000 . Uani d ? C(1) 0.1482(1) 0.13366(9) 0.5996(2) 0.0459(3) 1.000 . Uani d ? C(2) 0.2524(1) 0.2330(1) 0.6648(2) 0.0490(4) 1.000 . Uani d ? C(3) 0.2880(1) 0.26007(9) 0.9175(2) 0.0431(3) 1.000 . Uani d ? C(4) 0.31885(9) 0.15477(9) 0.9835(2) 0.0445(3) 1.000 . Uani d ? C(5) 0.25879(9) 0.03836(8) 0.8465(2) 0.0396(3) 1.000 . Uani d ? C(6) 0.2123(1) -0.03966(9) 1.0061(2) 0.0453(3) 1.000 . Uani d ? C(7) 0.1703(1) -0.16209(9) 0.8858(2) 0.0436(3) 1.000 . Uani d ? C(8) 0.2703(1) -0.21094(9) 0.7369(2) 0.0435(3) 1.000 . Uani d ? C(9) 0.3128(1) -0.1334(1) 0.5753(2) 0.0512(4) 1.000 . Uani d ? C(10) 0.3598(1) -0.0119(1) 0.6992(2) 0.0474(3) 1.000 . Uani d ? C(11) 0.3995(1) 0.3561(1) 0.9727(3) 0.0675(4) 1.000 . Uani d ? C(12) 0.1763(1) 0.2944(1) 1.0537(2) 0.0624(4) 1.000 . Uani d ? C(13) 0.2300(1) -0.33691(9) 0.6186(2) 0.0521(4) 1.000 . Uani d ? C(14) 0.1160(1) -0.3556(1) 0.4558(3) 0.0684(5) 1.000 . Uani d ? C(15) 0.3384(2) -0.3790(1) 0.4840(3) 0.0863(6) 1.000 . Uani d ? C(16) 0.1977(2) -0.4082(1) 0.7943(3) 0.0820(6) 1.000 . Uani d ? H(27) 0.0983(9) -0.0062(9) 0.667(2) 0.044 1.000 . Uiso d ? H(1) 0.326(1) 0.2143(9) 0.578(2) 0.054 1.000 . Uiso d ? H(2) 0.227(1) 0.2988(9) 0.625(2) 0.054 1.000 . Uiso d ? H(3) 0.280(1) -0.0348(8) 1.112(2) 0.050 1.000 . Uiso d ? H(4) 0.146(1) -0.0109(8) 1.093(2) 0.050 1.000 . Uiso d ? H(5) 0.1468(9) -0.2053(8) 1.007(2) 0.048 1.000 . Uiso d ? H(6) 0.097(1) -0.1694(8) 0.791(2) 0.048 1.000 . Uiso d ? H(7) 0.3397(9) -0.2080(8) 0.837(2) 0.048 1.000 . Uiso d ? H(8) 0.379(1) -0.1590(9) 0.483(2) 0.056 1.000 . Uiso d ? H(9) 0.243(1) -0.1343(9) 0.470(2) 0.056 1.000 . Uiso d ? H(10) 0.387(1) 0.0357(9) 0.589(2) 0.052 1.000 . Uiso d ? H(11) 0.430(1) -0.0106(9) 0.797(2) 0.052 1.000 . Uiso d ? H(12) 0.417(1) 0.374(1) 1.127(2) 0.076 1.000 . Uiso d ? H(13) 0.470(1) 0.329(1) 0.887(2) 0.076 1.000 . Uiso d ? H(14) 0.382(1) 0.424(1) 0.923(2) 0.076 1.000 . Uiso d ? H(15) 0.198(1) 0.316(1) 1.227(2) 0.070 1.000 . Uiso d ? H(16) 0.157(1) 0.366(1) 1.018(2) 0.070 1.000 . Uiso d ? H(17) 0.109(1) 0.232(1) 1.027(2) 0.070 1.000 . Uiso d ? H(18) 0.043(1) -0.335(1) 0.536(2) 0.077 1.000 . Uiso d ? H(19) 0.131(1) -0.310(1) 0.337(2) 0.077 1.000 . Uiso d ? H(20) 0.100(1) -0.436(1) 0.377(2) 0.077 1.000 . Uiso d ? H(21) 0.409(1) -0.364(1) 0.576(2) 0.098 1.000 . Uiso d ? H(22) 0.318(1) -0.462(1) 0.424(2) 0.098 1.000 . Uiso d ? H(23) 0.354(1) -0.344(1) 0.339(2) 0.098 1.000 . Uiso d ? H(24) 0.265(1) -0.396(1) 0.906(2) 0.094 1.000 . Uiso d ? H(25) 0.125(1) -0.391(1) 0.880(2) 0.094 1.000 . Uiso d ? H(26) 0.180(1) -0.488(1) 0.721(2) 0.094 1.000 . Uiso d ? loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O(1) 0.0624(5) 0.0549(5) 0.0728(6) 0.0012(4) -0.0332(5) 0.0196(4) O(2) 0.0710(6) 0.0604(5) 0.0716(6) 0.0082(4) -0.0376(5) 0.0051(4) N(1) 0.0362(5) 0.0408(5) 0.0557(6) -0.0019(4) -0.0145(4) 0.0137(5) C(1) 0.0444(6) 0.0447(7) 0.0470(7) 0.0045(5) -0.0089(5) 0.0093(5) C(2) 0.0505(7) 0.0474(7) 0.0470(7) -0.0007(6) -0.0046(6) 0.0128(6) C(3) 0.0407(6) 0.0418(6) 0.0435(6) 0.0001(5) -0.0034(5) 0.0072(5) C(4) 0.0358(6) 0.0510(7) 0.0441(6) 0.0059(5) -0.0065(5) 0.0054(5) C(5) 0.0330(6) 0.0441(6) 0.0407(6) 0.0059(5) -0.0071(5) 0.0078(5) C(6) 0.0454(7) 0.0519(7) 0.0401(6) 0.0122(6) 0.0001(5) 0.0102(5) C(7) 0.0442(7) 0.0475(7) 0.0412(7) 0.0069(5) -0.0006(5) 0.0151(5) C(8) 0.0408(6) 0.0477(7) 0.0425(6) 0.0105(5) -0.0059(5) 0.0085(5) C(9) 0.0499(7) 0.0531(7) 0.0487(7) 0.0092(6) 0.0105(6) 0.0065(6) C(10) 0.0392(6) 0.0520(7) 0.0496(7) 0.0032(5) 0.0020(5) 0.0111(6) C(11) 0.0645(9) 0.0582(9) 0.0705(9) -0.0109(7) -0.0162(7) 0.0104(8) C(12) 0.0666(9) 0.0618(9) 0.0621(8) 0.0200(7) 0.0090(7) 0.0136(7) C(13) 0.0559(7) 0.0455(7) 0.0537(7) 0.0113(6) -0.0057(6) 0.0066(5) C(14) 0.073(1) 0.0563(8) 0.066(1) -0.0009(8) -0.0176(8) 0.0021(7) C(15) 0.083(1) 0.069(1) 0.097(1) 0.0259(9) 0.0016(9) -0.0162(9) C(16) 0.123(2) 0.0483(8) 0.075(1) 0.0122(9) -0.0119(9) 0.0167(8) #============================================================================== # REFINEMENT DATA _refine_special_details ; ? ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme sigma _refine_ls_weighting_details 'w = 1/[\s^2^(Fo) + 0.00002|Fo|^2^]' _refine_ls_hydrogen_treatment refxyz _refine_ls_extinction_method 'Zachariasen (1967)' _refine_ls_extinction_coef 0.0000178(6) _refine_ls_extinction_expression 'equ(3) Acta Cryst.(1968) A24, p213.' _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1871 _refine_ls_number_parameters 254 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.0510 _refine_ls_R_factor_gt 0.0380 _refine_ls_wR_factor_all 0.0410 _refine_ls_wR_factor_ref 0.0400 _refine_ls_goodness_of_fit_all 2.940 _refine_ls_goodness_of_fit_ref 3.220 _refine_ls_shift/su_max 0.0000 _refine_ls_shift/su_mean 0.0000 _refine_diff_density_min -0.12 _refine_diff_density_max 0.16 #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.234(2) . . ? O2 C4 1.214(2) . . ? N1 C1 1.333(2) . . ? N1 C5 1.472(2) . . ? N1 H27 0.81(2) . . no C1 C2 1.501(3) . . ? C2 C3 1.526(3) . . ? C2 H1 0.99(2) . . no C2 H2 0.97(2) . . no C3 C4 1.518(2) . . ? C3 C11 1.522(3) . . ? C3 C12 1.533(3) . . ? C4 C5 1.530(2) . . ? C5 C6 1.530(2) . . ? C5 C10 1.540(3) . . ? C6 C7 1.519(3) . . ? C6 H3 0.95(2) . . no C6 H4 0.96(2) . . no C7 C8 1.529(3) . . ? C7 H5 1.00(2) . . no C7 H6 0.96(2) . . no C8 C9 1.526(3) . . ? C8 C13 1.551(3) . . ? C8 H7 0.95(2) . . no C9 C10 1.523(3) . . ? C9 H8 0.96(2) . . no C9 H9 0.98(2) . . no C10 H10 0.99(2) . . no C10 H11 0.96(2) . . no C11 H12 0.92(2) . . no C11 H13 0.98(2) . . no C11 H14 0.99(2) . . no C12 H15 1.04(2) . . no C12 H16 1.00(2) . . no C12 H17 0.95(2) . . no C13 C14 1.527(3) . . ? C13 C15 1.529(3) . . ? C13 C16 1.521(3) . . ? C14 H18 0.97(2) . . no C14 H19 1.00(2) . . no C14 H20 0.99(2) . . no C15 H21 0.91(3) . . no C15 H22 1.00(2) . . no C15 H23 1.06(2) . . no C16 H24 0.96(2) . . no C16 H25 0.97(3) . . no C16 H26 0.98(2) . . no #------------------------------------------------------------------------------ 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C5 125.1(2) . . . ? C1 N1 H27 117(1) . . . no C5 N1 H27 117(1) . . . no O1 C1 N1 122.6(2) . . . ? O1 C1 C2 121.5(2) . . . ? N1 C1 C2 115.9(2) . . . ? C1 C2 C3 112.3(2) . . . ? C1 C2 H1 107(1) . . . no C1 C2 H2 109(1) . . . no C3 C2 H1 110(1) . . . no C3 C2 H2 109(1) . . . no H1 C2 H2 109(2) . . . no C2 C3 C4 109.0(2) . . . ? C2 C3 C11 110.3(2) . . . ? C2 C3 C12 109.7(2) . . . ? C4 C3 C11 110.6(2) . . . ? C4 C3 C12 107.8(2) . . . ? C11 C3 C12 109.3(2) . . . ? O2 C4 C3 121.3(2) . . . ? O2 C4 C5 119.2(2) . . . ? C3 C4 C5 119.5(2) . . . ? N1 C5 C4 110.1(1) . . . ? N1 C5 C6 109.3(1) . . . ? N1 C5 C10 110.5(1) . . . ? C4 C5 C6 110.1(2) . . . ? C4 C5 C10 108.1(1) . . . ? C6 C5 C10 108.8(2) . . . ? C5 C6 C7 113.7(2) . . . ? C5 C6 H3 107(1) . . . no C5 C6 H4 109(1) . . . no C7 C6 H3 110(1) . . . no C7 C6 H4 111(1) . . . no H3 C6 H4 106(2) . . . no C6 C7 C8 113.2(2) . . . ? C6 C7 H5 106(1) . . . no C6 C7 H6 110(1) . . . no C8 C7 H5 111(1) . . . no C8 C7 H6 107(1) . . . no H5 C7 H6 108(1) . . . no C7 C8 C9 108.7(2) . . . ? C7 C8 C13 113.7(2) . . . ? C7 C8 H7 106(1) . . . no C9 C8 C13 114.2(2) . . . ? C9 C8 H7 108(1) . . . no C13 C8 H7 106(1) . . . no C8 C9 C10 112.5(2) . . . ? C8 C9 H8 112(1) . . . no C8 C9 H9 110(1) . . . no C10 C9 H8 108(1) . . . no C10 C9 H9 109(1) . . . no H8 C9 H9 106(2) . . . no C5 C10 C9 111.9(2) . . . ? C5 C10 H10 109(1) . . . no C5 C10 H11 108(1) . . . no C9 C10 H10 110(1) . . . no C9 C10 H11 109(1) . . . no H10 C10 H11 109(2) . . . no C3 C11 H12 109(1) . . . no C3 C11 H13 106(1) . . . no C3 C11 H14 111(1) . . . no H12 C11 H13 112(2) . . . no H12 C11 H14 109(2) . . . no H13 C11 H14 108(2) . . . no C3 C12 H15 112(1) . . . no C3 C12 H16 109(1) . . . no C3 C12 H17 109(1) . . . no H15 C12 H16 103(2) . . . no H15 C12 H17 108(2) . . . no H16 C12 H17 116(2) . . . no C8 C13 C14 112.3(2) . . . ? C8 C13 C15 109.6(2) . . . ? C8 C13 C16 110.2(2) . . . ? C14 C13 C15 108.2(2) . . . ? C14 C13 C16 108.3(2) . . . ? C15 C13 C16 108.2(2) . . . ? C13 C14 H18 111(1) . . . no C13 C14 H19 112(1) . . . no C13 C14 H20 108(1) . . . no H18 C14 H19 108(2) . . . no H18 C14 H20 110(2) . . . no H19 C14 H20 107(2) . . . no C13 C15 H21 109(2) . . . no C13 C15 H22 111(1) . . . no C13 C15 H23 112(1) . . . no H21 C15 H22 109(2) . . . no H21 C15 H23 111(2) . . . no H22 C15 H23 105(2) . . . no C13 C16 H24 111(2) . . . no C13 C16 H25 114(2) . . . no C13 C16 H26 110(1) . . . no H24 C16 H25 105(2) . . . no H24 C16 H26 109(2) . . . no H25 C16 H26 107(2) . . . no #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O1 N1 2.949(2) . 2_556 no O1 C7 3.384(2) . 2_556 no O1 O1 3.446(3) . 2_556 no O1 C14 3.562(3) . 2_556 no O1 C12 3.583(3) . 1_554 no O2 C2 3.513(3) . 1_556 no #------------------------------------------------------------------------------ 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag O1 C1 N1 C5 . . . . 171.8(2) no O1 C1 C2 C3 . . . . 139.7(2) no O2 C4 C3 C2 . . . . 152.4(2) no O2 C4 C3 C11 . . . . 30.9(3) no O2 C4 C3 C12 . . . . -88.5(2) no O2 C4 C5 N1 . . . . 165.6(2) no O2 C4 C5 C6 . . . . 45.0(2) no O2 C4 C5 C10 . . . . -73.7(2) no N1 C1 C2 C3 . . . . -38.9(3) no N1 C5 C4 C3 . . . . -14.9(2) no N1 C5 C6 C7 . . . . 68.2(2) no N1 C5 C10 C9 . . . . -65.7(2) no C1 N1 C5 C4 . . . . 36.7(2) no C1 N1 C5 C6 . . . . 157.7(2) no C1 N1 C5 C10 . . . . -82.6(2) no C1 C2 C3 C4 . . . . 54.6(2) no C1 C2 C3 C11 . . . . 176.2(2) no C1 C2 C3 C12 . . . . -63.3(2) no C2 C1 N1 C5 . . . . -9.6(3) no C2 C3 C4 C5 . . . . -27.0(2) no C3 C4 C5 C6 . . . . -135.5(2) no C3 C4 C5 C10 . . . . 105.8(2) no C4 C5 C6 C7 . . . . -170.8(2) no C4 C5 C10 C9 . . . . 173.8(2) no C5 C4 C3 C11 . . . . -148.5(2) no C5 C4 C3 C12 . . . . 92.1(2) no C5 C6 C7 C8 . . . . 54.1(2) no C5 C10 C9 C8 . . . . -58.3(2) no C6 C5 C10 C9 . . . . 54.3(2) no C6 C7 C8 C9 . . . . -53.3(2) no C6 C7 C8 C13 . . . . 178.3(2) no C7 C6 C5 C10 . . . . -52.5(2) no C7 C8 C9 C10 . . . . 55.7(2) no C7 C8 C13 C14 . . . . 62.5(2) no C7 C8 C13 C15 . . . . -177.2(2) no C7 C8 C13 C16 . . . . -58.3(2) no C9 C8 C13 C14 . . . . -63.0(2) no C9 C8 C13 C15 . . . . 57.3(3) no C9 C8 C13 C16 . . . . 176.2(2) no C10 C9 C8 C13 . . . . -176.2(2) no #------------------------------------------------------------------------------ #============================================================================== data__cee42d-3 _database_code_CSD 171041 #============================================================================== _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan for Windows version 1.06 (MSC, 1997-1999)' _computing_structure_solution ; SIR92 (Altomare, et. al. 1994) ; _computing_structure_refinement 'teXsan for Windows version 1.06 (MSC, 1997-1999)' _computing_publication_material 'teXsan for Windows version 1.06 (MSC, 1997-1999)' #------------------------------------------------------------------------------ _cell_length_a 10.999(1) _cell_length_b 5.926(6) _cell_length_c 26.445(2) _cell_angle_alpha 90 _cell_angle_beta 99.11(1) _cell_angle_gamma 90 _cell_volume 1702(1) _cell_formula_units_Z 4 _cell_measurement_temperature 299.2 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 18.4 _cell_measurement_theta_max 21.4 #------------------------------------------------------------------------------ _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c ' _symmetry_Int_Tables_number 14 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' ' -x,1/2+y,1/2-z' ' -x, -y, -z' ' +x,1/2-y,1/2+z' #------------------------------------------------------------------------------ _publ_section_exptl_prep ; ENTER EXPERIMENTAL SECTION ; _exptl_crystal_description 'prism' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.25 _exptl_crystal_density_diffrn 1.472 _exptl_crystal_density_meas 'not measured' _chemical_formula_weight 377.26 _chemical_formula_analytical ? _chemical_formula_sum 'C15 H24 I N O2 ' _chemical_formula_moiety 'C15 H24 I N O2 ' _chemical_formula_structural ? _chemical_compound_source ? _exptl_crystal_F_000 760.00 _exptl_absorpt_coefficient_mu 1.881 _exptl_absorpt_correction_type ; \y scans (North,Phillips & Matthews, 1968) ; _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.919 _exptl_special_details ; The scan width was (1.22+0.35tan\q)\% with an \w scan speed of 4\% per minute (up to 6 scans to achieve I/\s(I) > 10). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1. ; #============================================================================== # EXPERIMENTAL DATA _diffrn_special_details ; ? ; _diffrn_ambient_temperature 299.2 _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device 'Rigaku AFC6S' _diffrn_measurement_method \w-2\q _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% 0.99 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -2 0 4 -2 0 6 -1 -1 5 _diffrn_reflns_number 4544 _reflns_number_total 4328 _reflns_number_gt 2598 _reflns_threshold_expression I>2.00\s(I) _diffrn_reflns_av_R_equivalents 0.00990 _diffrn_reflns_av_sigmaI/netI 0.039 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 2.62 _diffrn_reflns_theta_max 27.58 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 0.01881 _diffrn_orient_matrix_UB_12 -0.01047 _diffrn_orient_matrix_UB_13 0.03818 _diffrn_orient_matrix_UB_21 -0.01714 _diffrn_orient_matrix_UB_22 0.16491 _diffrn_orient_matrix_UB_23 0.00269 _diffrn_orient_matrix_UB_31 -0.08849 _diffrn_orient_matrix_UB_32 -0.03417 _diffrn_orient_matrix_UB_33 0.00129 #------------------------------------------------------------------------------ loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 60 0.002 0.002 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; H 0 96 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; O 0 8 0.008 0.006 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; N 0 4 0.004 0.003 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; I 0 4 -0.726 1.812 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_refinement_flags _atom_site_adp_type _atom_site_calc_flag _atom_site_calc_attached_atom I(1) 0.34800(2) 0.41632(5) 0.841080(7) 0.10078(9) 1.000 . Uani d ? O(1) 0.1099(2) 0.6151(3) 0.58226(7) 0.0788(6) 1.000 . Uani d ? O(2) 0.1020(2) -0.0469(3) 0.71820(7) 0.0797(6) 1.000 . Uani d ? N(1) 0.2026(2) 0.2318(3) 0.68349(7) 0.0561(6) 1.000 . Uani d ? C(1) 0.2269(2) 0.3884(5) 0.76909(9) 0.0694(8) 1.000 . Uani d ? C(2) 0.2924(2) 0.2746(5) 0.72953(9) 0.0648(8) 1.000 . Uani d ? C(3) 0.3868(2) 0.4319(5) 0.7097(1) 0.0796(9) 1.000 . Uani d ? C(4) 0.3126(2) 0.5453(5) 0.6631(1) 0.0708(9) 1.000 . Uani d ? C(5) 0.2283(2) 0.3576(4) 0.63831(9) 0.0577(7) 1.000 . Uani d ? C(6) 0.1096(2) 0.4465(4) 0.60802(9) 0.0594(8) 1.000 . Uani d ? C(7) -0.0095(2) 0.3176(4) 0.6119(1) 0.0662(8) 1.000 . Uani d ? C(8) 0.0185(2) 0.0819(4) 0.6333(1) 0.0663(8) 1.000 . Uani d ? C(9) 0.1108(2) 0.0791(4) 0.6820(1) 0.0608(8) 1.000 . Uani d ? C(10) 0.2929(2) 0.1987(4) 0.6037(1) 0.0684(8) 1.000 . Uani d ? C(11) 0.3144(3) 0.2887(7) 0.5521(1) 0.107(1) 1.000 . Uani d ? C(12) 0.425(1) 0.391(2) 0.5532(3) 0.483(7) 1.000 . Uani d ? C(13) 0.3193(8) 0.121(1) 0.5155(2) 0.318(4) 1.000 . Uani d ? C(14) -0.0883(3) 0.3045(6) 0.5593(1) 0.112(1) 1.000 . Uani d ? C(15) -0.0758(3) 0.4540(5) 0.6490(1) 0.087(1) 1.000 . Uani d ? H(1) 0.1569 0.3014 0.7737 0.083 1.000 . Uiso c ? H(2) 0.2012 0.5350 0.7574 0.083 1.000 . Uiso c ? H(3) 0.3305 0.1382 0.7426 0.078 1.000 . Uiso c ? H(4) 0.4180 0.5404 0.7348 0.096 1.000 . Uiso c ? H(5) 0.4532 0.3476 0.7002 0.096 1.000 . Uiso c ? H(6) 0.2658 0.6676 0.6731 0.085 1.000 . Uiso c ? H(7) 0.3650 0.5983 0.6404 0.085 1.000 . Uiso c ? H(8) -0.0560 0.0163 0.6401 0.080 1.000 . Uiso c ? H(9) 0.0503 -0.0055 0.6083 0.080 1.000 . Uiso c ? H(10) 0.3710 0.1597 0.6225 0.082 1.000 . Uiso c ? H(11) 0.2437 0.0668 0.5975 0.082 1.000 . Uiso c ? H(12) 0.2506 0.3922 0.5397 0.129 1.000 . Uiso c ? H(13) 0.4602 0.4220 0.5877 0.578 1.000 . Uiso c ? H(14) 0.4783 0.2964 0.5379 0.578 1.000 . Uiso c ? H(15) 0.4137 0.5299 0.5347 0.578 1.000 . Uiso c ? H(16) 0.3214 -0.0227 0.5314 0.382 1.000 . Uiso c ? H(17) 0.2478 0.1313 0.4900 0.382 1.000 . Uiso c ? H(18) 0.3906 0.1411 0.5001 0.382 1.000 . Uiso c ? H(19) -0.1726 0.2932 0.5630 0.134 1.000 . Uiso c ? H(20) -0.0762 0.4366 0.5404 0.134 1.000 . Uiso c ? H(21) -0.0653 0.1756 0.5417 0.134 1.000 . Uiso c ? H(22) -0.0493 0.4035 0.6831 0.105 1.000 . Uiso c ? H(23) -0.0568 0.6095 0.6465 0.105 1.000 . Uiso c ? H(24) -0.1622 0.4329 0.6403 0.105 1.000 . Uiso c ? loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 I(1) 0.0711(1) 0.1521(3) 0.0779(1) -0.0103(1) 0.00804(9) -0.0107(1) O(1) 0.092(1) 0.054(1) 0.093(1) 0.012(1) 0.026(1) 0.018(1) O(2) 0.097(1) 0.058(1) 0.089(1) -0.009(1) 0.030(1) 0.014(1) N(1) 0.061(1) 0.050(1) 0.061(1) -0.004(1) 0.0177(9) 0.002(1) C(1) 0.059(1) 0.083(2) 0.067(2) -0.003(1) 0.013(1) -0.002(1) C(2) 0.057(1) 0.066(2) 0.075(2) 0.004(1) 0.019(1) 0.006(1) C(3) 0.065(2) 0.091(2) 0.088(2) -0.010(2) 0.027(1) -0.009(2) C(4) 0.071(2) 0.062(2) 0.084(2) -0.013(1) 0.026(1) 0.001(2) C(5) 0.063(1) 0.043(2) 0.072(2) 0.001(1) 0.024(1) 0.003(1) C(6) 0.075(2) 0.039(2) 0.067(2) 0.007(1) 0.022(1) -0.002(1) C(7) 0.065(2) 0.054(2) 0.079(2) 0.000(1) 0.011(1) -0.003(1) C(8) 0.076(2) 0.042(2) 0.084(2) -0.010(1) 0.022(1) -0.008(1) C(9) 0.072(2) 0.038(1) 0.076(2) 0.008(1) 0.026(1) 0.000(1) C(10) 0.073(2) 0.060(2) 0.078(2) 0.012(1) 0.030(1) 0.001(1) C(11) 0.133(3) 0.117(3) 0.083(2) 0.052(2) 0.053(2) 0.011(2) C(12) 0.65(2) 0.67(2) 0.195(6) -0.51(2) 0.271(9) -0.132(8) C(13) 0.52(1) 0.307(9) 0.181(5) -0.221(9) 0.220(7) -0.146(6) C(14) 0.112(3) 0.108(3) 0.104(2) -0.017(2) -0.019(2) 0.013(2) C(15) 0.077(2) 0.055(2) 0.139(3) 0.008(2) 0.043(2) -0.006(2) #============================================================================== # REFINEMENT DATA _refine_special_details ; ? ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme sigma _refine_ls_weighting_details 'w = 1/[\s^2^(Fo) + 0.00002|Fo|^2^]' _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method 'Zachariasen (1967)' _refine_ls_extinction_coef 0.00000025(3) _refine_ls_extinction_expression 'equ(3) Acta Cryst.(1968) A24, p213.' _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 2598 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.0715 _refine_ls_R_factor_gt 0.0410 _refine_ls_wR_factor_all 0.0420 _refine_ls_wR_factor_ref 0.0400 _refine_ls_goodness_of_fit_all 2.525 _refine_ls_goodness_of_fit_ref 3.050 _refine_ls_shift/su_max 0.0000 _refine_ls_shift/su_mean 0.0001 _refine_diff_density_min -0.51 _refine_diff_density_max 0.56 #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 C1 2.150(4) . . ? O1 C6 1.210(5) . . ? O2 C9 1.230(5) . . ? N1 C2 1.463(5) . . ? N1 C5 1.473(5) . . ? N1 C9 1.353(5) . . ? C1 C2 1.520(6) . . ? C1 H1 0.95 . . no C1 H2 0.95 . . no C2 C3 1.548(6) . . ? C2 H3 0.95 . . no C3 C4 1.521(7) . . ? C3 H4 0.95 . . no C3 H5 0.95 . . no C4 C5 1.528(6) . . ? C4 H6 0.95 . . no C4 H7 0.95 . . no C5 C6 1.515(6) . . ? C5 C10 1.560(5) . . ? C6 C7 1.533(6) . . ? C7 C8 1.520(6) . . ? C7 C14 1.520(6) . . ? C7 C15 1.541(6) . . ? C8 C9 1.508(6) . . ? C8 H8 0.95 . . no C8 H9 0.95 . . no C10 C11 1.519(7) . . ? C10 H10 0.95 . . no C10 H11 0.95 . . no C11 C12 1.36(1) . . ? C11 C13 1.39(1) . . ? C11 H12 0.95 . . no C12 H13 0.95 . . no C12 H14 0.94 . . no C12 H15 0.96 . . no C13 H16 0.95 . . no C13 H17 0.95 . . no C13 H18 0.95 . . no C14 H19 0.95 . . no C14 H20 0.95 . . no C14 H21 0.95 . . no C15 H22 0.95 . . no C15 H23 0.95 . . no C15 H24 0.95 . . no #------------------------------------------------------------------------------ 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C5 113.3(3) . . . ? C2 N1 C9 122.9(3) . . . ? C5 N1 C9 123.6(4) . . . ? I1 C1 C2 110.4(3) . . . ? I1 C1 H1 109.2 . . . no I1 C1 H2 109.2 . . . no C2 C1 H1 109.2 . . . no C2 C1 H2 109.2 . . . no H1 C1 H2 109.5 . . . no N1 C2 C1 108.6(3) . . . ? N1 C2 C3 102.9(3) . . . ? N1 C2 H3 110.9 . . . no C1 C2 C3 112.5(4) . . . ? C1 C2 H3 110.9 . . . no C3 C2 H3 110.9 . . . no C2 C3 C4 103.8(4) . . . ? C2 C3 H4 110.9 . . . no C2 C3 H5 110.9 . . . no C4 C3 H4 110.9 . . . no C4 C3 H5 110.9 . . . no H4 C3 H5 109.5 . . . no C3 C4 C5 103.7(4) . . . ? C3 C4 H6 110.9 . . . no C3 C4 H7 110.9 . . . no C5 C4 H6 110.9 . . . no C5 C4 H7 110.9 . . . no H6 C4 H7 109.5 . . . no N1 C5 C4 101.6(3) . . . ? N1 C5 C6 110.2(3) . . . ? N1 C5 C10 109.5(3) . . . ? C4 C5 C6 112.8(4) . . . ? C4 C5 C10 112.9(3) . . . ? C6 C5 C10 109.5(3) . . . ? O1 C6 C5 120.4(4) . . . ? O1 C6 C7 121.9(4) . . . ? C5 C6 C7 117.7(4) . . . ? C6 C7 C8 111.0(4) . . . ? C6 C7 C14 109.5(4) . . . ? C6 C7 C15 106.1(4) . . . ? C8 C7 C14 110.3(4) . . . ? C8 C7 C15 109.5(4) . . . ? C14 C7 C15 110.5(4) . . . ? C7 C8 C9 113.4(4) . . . ? C7 C8 H8 108.5 . . . no C7 C8 H9 108.5 . . . no C9 C8 H8 108.5 . . . no C9 C8 H9 108.5 . . . no H8 C8 H9 109.5 . . . no O2 C9 N1 122.2(4) . . . ? O2 C9 C8 123.2(4) . . . ? N1 C9 C8 114.6(4) . . . ? C5 C10 C11 117.7(4) . . . ? C5 C10 H10 107.4 . . . no C5 C10 H11 107.4 . . . no C11 C10 H10 107.4 . . . no C11 C10 H11 107.4 . . . no H10 C10 H11 109.5 . . . no C10 C11 C12 113.8(7) . . . ? C10 C11 C13 113.6(7) . . . ? C10 C11 H12 109.0 . . . no C12 C11 C13 101.6(9) . . . ? C12 C11 H12 109.3 . . . no C13 C11 H12 109.2 . . . no C11 C12 H13 109.5 . . . no C11 C12 H14 109.8 . . . no C11 C12 H15 109.0 . . . no H13 C12 H14 110.1 . . . no H13 C12 H15 109.0 . . . no H14 C12 H15 109.4 . . . no C11 C13 H16 109.6 . . . no C11 C13 H17 109.1 . . . no C11 C13 H18 109.5 . . . no H16 C13 H17 109.4 . . . no H16 C13 H18 110.0 . . . no H17 C13 H18 109.3 . . . no C7 C14 H19 109.5 . . . no C7 C14 H20 109.5 . . . no C7 C14 H21 109.5 . . . no H19 C14 H20 109.5 . . . no H19 C14 H21 109.5 . . . no H20 C14 H21 109.5 . . . no C7 C15 H22 109.5 . . . no C7 C15 H23 109.5 . . . no C7 C15 H24 109.5 . . . no H22 C15 H23 109.5 . . . no H22 C15 H24 109.5 . . . no H23 C15 H24 109.5 . . . no #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O1 C8 3.304(6) . 1_565 no O2 C15 3.568(6) . 2_546 no #------------------------------------------------------------------------------ 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag I1 C1 C2 N1 . . . . 172.5(3) no I1 C1 C2 C3 . . . . -74.3(4) no O1 C6 C5 N1 . . . . 152.5(4) no O1 C6 C5 C4 . . . . 39.7(5) no O1 C6 C5 C10 . . . . -87.0(5) no O1 C6 C7 C8 . . . . 163.7(4) no O1 C6 C7 C14 . . . . 41.8(6) no O1 C6 C7 C15 . . . . -77.5(5) no O2 C9 N1 C2 . . . . -5.7(6) no O2 C9 N1 C5 . . . . 169.2(4) no O2 C9 C8 C7 . . . . 140.6(4) no N1 C2 C3 C4 . . . . 25.5(4) no N1 C5 C4 C3 . . . . 34.9(4) no N1 C5 C6 C7 . . . . -26.7(5) no N1 C5 C10 C11 . . . . 173.3(4) no N1 C9 C8 C7 . . . . -37.4(5) no C1 C2 N1 C5 . . . . 115.9(4) no C1 C2 N1 C9 . . . . -68.7(5) no C1 C2 C3 C4 . . . . -91.1(4) no C2 N1 C5 C4 . . . . -19.7(4) no C2 N1 C5 C6 . . . . -139.5(4) no C2 N1 C5 C10 . . . . 100.0(4) no C2 N1 C9 C8 . . . . 172.4(3) no C2 C3 C4 C5 . . . . -38.0(4) no C3 C2 N1 C5 . . . . -3.5(4) no C3 C2 N1 C9 . . . . 171.9(4) no C3 C4 C5 C6 . . . . 152.9(3) no C3 C4 C5 C10 . . . . -82.3(4) no C4 C5 N1 C9 . . . . 165.0(4) no C4 C5 C6 C7 . . . . -139.4(4) no C4 C5 C10 C11 . . . . -74.3(6) no C5 N1 C9 C8 . . . . -12.7(5) no C5 C6 C7 C8 . . . . -17.1(5) no C5 C6 C7 C14 . . . . -139.0(4) no C5 C6 C7 C15 . . . . 101.7(4) no C5 C10 C11 C12 . . . . 91(1) no C5 C10 C11 C13 . . . . -152.9(8) no C6 C5 N1 C9 . . . . 45.2(5) no C6 C5 C10 C11 . . . . 52.4(6) no C6 C7 C8 C9 . . . . 50.5(5) no C7 C6 C5 C10 . . . . 93.8(4) no C9 N1 C5 C10 . . . . -75.3(5) no C9 C8 C7 C14 . . . . 171.9(4) no C9 C8 C7 C15 . . . . -66.3(5) no #------------------------------------------------------------------------------ #============================================================================== data__cee54b-4 _database_code_CSD 171042 #============================================================================== _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan for Windows version 1.06 (MSC, 1997-1999)' _computing_structure_solution ; SIR92 (Altomare, et. al. 1994) ; _computing_structure_refinement 'teXsan for Windows version 1.06 (MSC, 1997-1999)' _computing_publication_material 'teXsan for Windows version 1.06 (MSC, 1997-1999)' #------------------------------------------------------------------------------ _cell_length_a 13.151(3) _cell_length_b 21.506(3) _cell_length_c 7.204(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2037.5(7) _cell_formula_units_Z 4 _cell_measurement_temperature 299.2 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10.6 _cell_measurement_theta_max 12.1 #------------------------------------------------------------------------------ _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21 ' _symmetry_Int_Tables_number 19 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' '1/2-x, -y,1/2+z' '1/2+x,1/2-y, -z' ' -x,1/2+y,1/2-z' #------------------------------------------------------------------------------ _publ_section_exptl_prep ; ENTER EXPERIMENTAL SECTION ; _exptl_crystal_description 'prism' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.380 _exptl_crystal_density_meas 'not measured' _chemical_formula_weight 423.41 _chemical_formula_analytical ? _chemical_formula_sum 'C16 H30 I N O2 Si ' _chemical_formula_moiety 'C16 H30 I N O2 Si ' _chemical_formula_structural ? _chemical_compound_source ? _exptl_crystal_F_000 864.00 _exptl_absorpt_coefficient_mu 1.635 _exptl_absorpt_correction_type ; \y scans (North,Phillips & Matthews, 1968) ; _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.785 _exptl_special_details ; The scan width was (1.52+0.35tan\q)\% with an \w scan speed of 4\% per minute (up to 6 scans to achieve I/\s(I) > 10). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1. ; #============================================================================== # EXPERIMENTAL DATA _diffrn_special_details ; ? ; _diffrn_ambient_temperature 299.2 _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device 'Rigaku AFC6S' _diffrn_measurement_method \w-2\q _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% -19.30 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 2 -1 -1 2 1 -1 3 -4 0 _diffrn_reflns_number 5259 _reflns_number_total 2631 _reflns_number_gt 1381 _reflns_threshold_expression I>2.00\s(I) _diffrn_reflns_av_R_equivalents 0.04170 _diffrn_reflns_av_sigmaI/netI 0.085 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.83 _diffrn_reflns_theta_max 27.55 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 0.07536 _diffrn_orient_matrix_UB_12 0.00584 _diffrn_orient_matrix_UB_13 0.00638 _diffrn_orient_matrix_UB_21 0.00947 _diffrn_orient_matrix_UB_22 -0.04612 _diffrn_orient_matrix_UB_23 0.00358 _diffrn_orient_matrix_UB_31 0.00371 _diffrn_orient_matrix_UB_32 -0.00092 _diffrn_orient_matrix_UB_33 -0.13862 #------------------------------------------------------------------------------ loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 64 0.002 0.002 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; H 0 120 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; O 0 8 0.008 0.006 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; N 0 4 0.004 0.003 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; I 0 4 -0.726 1.812 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; Si 0 4 0.072 0.071 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_refinement_flags _atom_site_adp_type _atom_site_calc_flag _atom_site_calc_attached_atom I(1) -0.67430(5) -0.03538(3) -0.7997(1) 0.0990(2) 1.000 . Uani d ? Si(1) -0.5712(2) -0.3522(1) -0.1314(3) 0.0616(6) 1.000 . Uani d ? O(1) -0.4754(5) -0.2121(3) -0.7851(7) 0.084(2) 1.000 . Uani d ? O(2) -0.5348(3) -0.2973(2) -0.2761(6) 0.051(1) 1.000 . Uani d ? N(1) -0.5097(4) -0.1795(3) -0.4965(7) 0.050(2) 1.000 . Uani d ? C(1) -0.4592(6) -0.2166(4) -0.617(1) 0.058(2) 1.000 . Uani d ? C(2) -0.3869(6) -0.2641(4) -0.546(1) 0.062(2) 1.000 . Uani d ? C(3) -0.3651(5) -0.2611(3) -0.336(1) 0.062(2) 1.000 . Uani d ? C(4) -0.4641(5) -0.2492(3) -0.2342(9) 0.050(2) 1.000 . Uani d ? C(5) -0.5059(5) -0.1859(3) -0.2881(9) 0.051(2) 1.000 . Uani d ? C(6) -0.6173(5) -0.1746(3) -0.241(1) 0.069(3) 1.000 . Uani d ? C(7) -0.6539(6) -0.1254(3) -0.380(1) 0.075(3) 1.000 . Uani d ? C(8) -0.5954(5) -0.1411(3) -0.559(1) 0.057(2) 1.000 . Uani d ? C(9) -0.6642(7) -0.3186(4) 0.039(1) 0.099(3) 1.000 . Uani d ? C(10) -0.4614(8) -0.3844(4) -0.004(2) 0.111(4) 1.000 . Uani d ? C(11) -0.6348(6) -0.4109(3) -0.283(1) 0.072(2) 1.000 . Uani d ? C(12) -0.7200(8) -0.3821(4) -0.393(2) 0.120(4) 1.000 . Uani d ? C(13) -0.6795(8) -0.4620(4) -0.163(2) 0.126(4) 1.000 . Uani d ? C(14) -0.5549(9) -0.4403(4) -0.417(2) 0.130(4) 1.000 . Uani d ? C(15) -0.4395(6) -0.1337(3) -0.210(1) 0.075(3) 1.000 . Uani d ? C(16) -0.5539(5) -0.0846(3) -0.662(1) 0.073(3) 1.000 . Uani d ? H(1) -0.4142 -0.3041 -0.5722 0.072 1.000 . Uiso c ? H(2) -0.3241 -0.2592 -0.6089 0.072 1.000 . Uiso c ? H(3) -0.3374 -0.2992 -0.2948 0.076 1.000 . Uiso c ? H(4) -0.3190 -0.2282 -0.3110 0.076 1.000 . Uiso c ? H(5) -0.4498 -0.2491 -0.1052 0.062 1.000 . Uiso c ? H(6) -0.6556 -0.2119 -0.2502 0.082 1.000 . Uiso c ? H(7) -0.6239 -0.1588 -0.1165 0.082 1.000 . Uiso c ? H(8) -0.7253 -0.1297 -0.4028 0.094 1.000 . Uiso c ? H(9) -0.6390 -0.0850 -0.3412 0.094 1.000 . Uiso c ? H(10) -0.6370 -0.1651 -0.6389 0.070 1.000 . Uiso c ? H(11) -0.6398 -0.3266 0.1607 0.116 1.000 . Uiso c ? H(12) -0.6691 -0.2755 0.0184 0.116 1.000 . Uiso c ? H(13) -0.7278 -0.3381 0.0213 0.116 1.000 . Uiso c ? H(14) -0.4786 -0.3796 0.1301 0.128 1.000 . Uiso c ? H(15) -0.4540 -0.4253 -0.0303 0.128 1.000 . Uiso c ? H(16) -0.4048 -0.3597 -0.0271 0.128 1.000 . Uiso c ? H(17) -0.7708 -0.3639 -0.3096 0.144 1.000 . Uiso c ? H(18) -0.6967 -0.3491 -0.4712 0.144 1.000 . Uiso c ? H(19) -0.7550 -0.4118 -0.4679 0.144 1.000 . Uiso c ? H(20) -0.6686 -0.4538 -0.0353 0.148 1.000 . Uiso c ? H(21) -0.7450 -0.4714 -0.1906 0.148 1.000 . Uiso c ? H(22) -0.6376 -0.5012 -0.1875 0.148 1.000 . Uiso c ? H(23) -0.5040 -0.4594 -0.3422 0.159 1.000 . Uiso c ? H(24) -0.5875 -0.4697 -0.4912 0.159 1.000 . Uiso c ? H(25) -0.5261 -0.4082 -0.4882 0.159 1.000 . Uiso c ? H(26) -0.4408 -0.1355 -0.0784 0.090 1.000 . Uiso c ? H(27) -0.3722 -0.1384 -0.2533 0.090 1.000 . Uiso c ? H(28) -0.4660 -0.0947 -0.2499 0.090 1.000 . Uiso c ? H(29) -0.5047 -0.0981 -0.7510 0.088 1.000 . Uiso c ? H(30) -0.5207 -0.0576 -0.5752 0.088 1.000 . Uiso c ? loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 I(1) 0.1053(5) 0.0857(4) 0.1060(5) 0.0191(4) -0.0252(4) 0.0161(4) Si(1) 0.066(1) 0.066(1) 0.052(1) 0.003(1) 0.007(1) 0.010(1) O(1) 0.119(5) 0.092(4) 0.042(3) 0.014(4) -0.002(4) -0.014(3) O(2) 0.057(3) 0.053(3) 0.042(3) -0.008(2) 0.000(3) 0.001(2) N(1) 0.051(3) 0.060(4) 0.039(3) -0.008(3) -0.001(3) -0.008(3) C(1) 0.064(5) 0.069(5) 0.041(4) -0.006(4) 0.005(4) -0.009(4) C(2) 0.066(5) 0.071(5) 0.048(4) 0.006(4) 0.011(4) -0.004(4) C(3) 0.047(4) 0.068(4) 0.071(6) -0.002(3) -0.003(4) 0.003(4) C(4) 0.059(4) 0.061(4) 0.030(4) -0.005(4) 0.002(3) -0.000(3) C(5) 0.053(4) 0.064(4) 0.036(4) 0.004(3) -0.002(4) -0.016(4) C(6) 0.063(5) 0.071(5) 0.072(6) -0.001(4) 0.008(4) -0.017(4) C(7) 0.067(5) 0.070(5) 0.087(6) 0.010(4) 0.012(5) 0.006(4) C(8) 0.055(4) 0.060(4) 0.056(5) -0.006(4) -0.010(4) -0.004(4) C(9) 0.124(8) 0.106(6) 0.067(5) -0.015(7) 0.028(7) -0.009(5) C(10) 0.119(8) 0.111(8) 0.104(8) -0.003(7) -0.013(7) 0.046(7) C(11) 0.098(5) 0.037(3) 0.080(6) -0.006(4) 0.008(5) 0.010(4) C(12) 0.141(9) 0.090(7) 0.129(9) -0.001(6) -0.062(8) -0.002(7) C(13) 0.151(8) 0.077(5) 0.151(9) -0.029(7) -0.003(9) 0.023(7) C(14) 0.18(1) 0.093(7) 0.121(9) -0.022(7) 0.058(9) -0.030(7) C(15) 0.093(6) 0.081(5) 0.051(4) -0.012(4) -0.007(5) -0.025(4) C(16) 0.070(5) 0.066(5) 0.083(6) -0.005(4) -0.008(5) 0.011(5) #============================================================================== # REFINEMENT DATA _refine_special_details ; ? ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme sigma _refine_ls_weighting_details 'w = 1/[\s^2^(Fo) + 0.00016|Fo|^2^]' _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method 'Zachariasen (1967)' _refine_ls_extinction_coef 0.00000084(8) _refine_ls_extinction_expression 'equ(3) Acta Cryst.(1968) A24, p213.' _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1381 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.1281 _refine_ls_R_factor_gt 0.0440 _refine_ls_wR_factor_all 0.0540 _refine_ls_wR_factor_ref 0.0450 _refine_ls_goodness_of_fit_all 1.407 _refine_ls_goodness_of_fit_ref 1.670 _refine_ls_shift/su_max 0.0000 _refine_ls_shift/su_mean 0.0000 _refine_diff_density_min -0.41 _refine_diff_density_max 0.41 #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag I(1) C(16) 2.148(9) . . ? Si(1) O(2) 1.647(6) . . ? Si(1) C(9) 1.88(1) . . ? Si(1) C(10) 1.85(1) . . ? Si(1) C(11) 1.87(1) . . ? O(1) C(1) 1.24(1) . . ? O(2) C(4) 1.422(9) . . ? N(1) C(1) 1.35(1) . . ? N(1) C(5) 1.51(1) . . ? N(1) C(8) 1.47(1) . . ? C(1) C(2) 1.49(1) . . ? C(2) C(3) 1.54(1) . . ? C(2) H(1) 0.95 . . no C(2) H(2) 0.95 . . no C(3) C(4) 1.51(1) . . ? C(3) H(3) 0.94 . . no C(3) H(4) 0.95 . . no C(4) C(5) 1.52(1) . . ? C(4) H(5) 0.95 . . no C(5) C(6) 1.52(1) . . ? C(5) C(15) 1.53(1) . . ? C(6) C(7) 1.54(1) . . ? C(6) H(6) 0.95 . . no C(6) H(7) 0.96 . . no C(7) C(8) 1.54(1) . . ? C(7) H(8) 0.96 . . no C(7) H(9) 0.93 . . no C(8) C(16) 1.52(1) . . ? C(8) H(10) 0.95 . . no C(9) H(11) 0.95 . . no C(9) H(12) 0.94 . . no C(9) H(13) 0.94 . . no C(10) H(14) 1.00 . . no C(10) H(15) 0.90 . . no C(10) H(16) 0.93 . . no C(11) C(12) 1.50(1) . . ? C(11) C(13) 1.52(1) . . ? C(11) C(14) 1.56(2) . . ? C(12) H(17) 0.98 . . no C(12) H(18) 0.96 . . no C(12) H(19) 0.96 . . no C(13) H(20) 0.95 . . no C(13) H(21) 0.91 . . no C(13) H(22) 1.02 . . no C(14) H(23) 0.95 . . no C(14) H(24) 0.94 . . no C(14) H(25) 0.94 . . no C(15) H(26) 0.95 . . no C(15) H(27) 0.94 . . no C(15) H(28) 0.95 . . no C(16) H(29) 0.96 . . no C(16) H(30) 0.96 . . no #------------------------------------------------------------------------------ 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O(2) Si(1) C(9) 109.1(4) . . . ? O(2) Si(1) C(10) 110.9(4) . . . ? O(2) Si(1) C(11) 104.2(4) . . . ? C(9) Si(1) C(10) 109.2(6) . . . ? C(9) Si(1) C(11) 110.5(5) . . . ? C(10) Si(1) C(11) 112.8(5) . . . ? Si(1) O(2) C(4) 125.2(5) . . . ? C(1) N(1) C(5) 124.5(8) . . . ? C(1) N(1) C(8) 120.9(8) . . . ? C(5) N(1) C(8) 112.5(7) . . . ? O(1) C(1) N(1) 120(1) . . . ? O(1) C(1) C(2) 120.0(9) . . . ? N(1) C(1) C(2) 120.1(9) . . . ? C(1) C(2) C(3) 115.2(8) . . . ? C(1) C(2) H(1) 108.3 . . . no C(1) C(2) H(2) 108.5 . . . no C(3) C(2) H(1) 107.6 . . . no C(3) C(2) H(2) 107.6 . . . no H(1) C(2) H(2) 109.6 . . . no C(2) C(3) C(4) 108.8(7) . . . ? C(2) C(3) H(3) 109.9 . . . no C(2) C(3) H(4) 109.4 . . . no C(4) C(3) H(3) 109.2 . . . no C(4) C(3) H(4) 109.5 . . . no H(3) C(3) H(4) 110.1 . . . no O(2) C(4) C(3) 109.7(7) . . . ? O(2) C(4) C(5) 111.1(6) . . . ? O(2) C(4) H(5) 109.8 . . . no C(3) C(4) C(5) 109.8(7) . . . ? C(3) C(4) H(5) 107.6 . . . no C(5) C(4) H(5) 108.7 . . . no N(1) C(5) C(4) 110.5(7) . . . ? N(1) C(5) C(6) 100.2(7) . . . ? N(1) C(5) C(15) 108.5(8) . . . ? C(4) C(5) C(6) 115.7(8) . . . ? C(4) C(5) C(15) 110.9(7) . . . ? C(6) C(5) C(15) 110.4(7) . . . ? C(5) C(6) C(7) 105.3(8) . . . ? C(5) C(6) H(6) 111.0 . . . no C(5) C(6) H(7) 110.6 . . . no C(7) C(6) H(6) 111.6 . . . no C(7) C(6) H(7) 109.6 . . . no H(6) C(6) H(7) 108.6 . . . no C(6) C(7) C(8) 103.8(7) . . . ? C(6) C(7) H(8) 110.6 . . . no C(6) C(7) H(9) 112.3 . . . no C(8) C(7) H(8) 109.0 . . . no C(8) C(7) H(9) 110.5 . . . no H(8) C(7) H(9) 110.4 . . . no N(1) C(8) C(7) 104.6(7) . . . ? N(1) C(8) C(16) 108.8(7) . . . ? N(1) C(8) H(10) 109.0 . . . no C(7) C(8) C(16) 114.2(8) . . . ? C(7) C(8) H(10) 109.8 . . . no C(16) C(8) H(10) 110.1 . . . no Si(1) C(9) H(11) 108.3 . . . no Si(1) C(9) H(12) 108.6 . . . no Si(1) C(9) H(13) 108.4 . . . no H(11) C(9) H(12) 110.5 . . . no H(11) C(9) H(13) 110.2 . . . no H(12) C(9) H(13) 110.8 . . . no Si(1) C(10) H(14) 105.3 . . . no Si(1) C(10) H(15) 110.2 . . . no Si(1) C(10) H(16) 108.8 . . . no H(14) C(10) H(15) 109.2 . . . no H(14) C(10) H(16) 107.1 . . . no H(15) C(10) H(16) 115.7 . . . no Si(1) C(11) C(12) 111.2(7) . . . ? Si(1) C(11) C(13) 109.3(8) . . . ? Si(1) C(11) C(14) 109.5(8) . . . ? C(12) C(11) C(13) 108(1) . . . ? C(12) C(11) C(14) 110(1) . . . ? C(13) C(11) C(14) 108.7(9) . . . ? C(11) C(12) H(17) 110.7 . . . no C(11) C(12) H(18) 112.2 . . . no C(11) C(12) H(19) 112.5 . . . no H(17) C(12) H(18) 106.3 . . . no H(17) C(12) H(19) 106.6 . . . no H(18) C(12) H(19) 108.2 . . . no C(11) C(13) H(20) 111.0 . . . no C(11) C(13) H(21) 113.8 . . . no C(11) C(13) H(22) 106.8 . . . no H(20) C(13) H(21) 113.6 . . . no H(20) C(13) H(22) 104.0 . . . no H(21) C(13) H(22) 107.0 . . . no C(11) C(14) H(23) 107.5 . . . no C(11) C(14) H(24) 108.7 . . . no C(11) C(14) H(25) 108.2 . . . no H(23) C(14) H(24) 110.6 . . . no H(23) C(14) H(25) 110.1 . . . no H(24) C(14) H(25) 111.6 . . . no C(5) C(15) H(26) 109.1 . . . no C(5) C(15) H(27) 109.7 . . . no C(5) C(15) H(28) 109.1 . . . no H(26) C(15) H(27) 110.0 . . . no H(26) C(15) H(28) 109.2 . . . no H(27) C(15) H(28) 109.7 . . . no I(1) C(16) C(8) 110.8(6) . . . ? I(1) C(16) H(29) 109.6 . . . no I(1) C(16) H(30) 109.8 . . . no C(8) C(16) H(29) 109.0 . . . no C(8) C(16) H(30) 109.3 . . . no H(29) C(16) H(30) 108.2 . . . no #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O(1) C(4) 3.34(1) . 1_554 no O(1) C(15) 3.53(1) . 1_554 no #------------------------------------------------------------------------------ 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag I(1) C(16) C(8) N(1) . . . . 169.6(6) no I(1) C(16) C(8) C(7) . . . . -74.0(9) no Si(1) O(2) C(4) C(3) . . . . 108.1(7) no Si(1) O(2) C(4) C(5) . . . . -130.3(6) no O(1) C(1) N(1) C(5) . . . . 172.2(9) no O(1) C(1) N(1) C(8) . . . . 10(2) no O(1) C(1) C(2) C(3) . . . . 174(1) no O(2) Si(1) C(11) C(12) . . . . -56.4(9) no O(2) Si(1) C(11) C(13) . . . . -175.5(7) no O(2) Si(1) C(11) C(14) . . . . 65.6(8) no O(2) C(4) C(3) C(2) . . . . 58(1) no O(2) C(4) C(5) N(1) . . . . -70.5(9) no O(2) C(4) C(5) C(6) . . . . 42.4(9) no O(2) C(4) C(5) C(15) . . . . 169.2(8) no N(1) C(1) C(2) C(3) . . . . -8(1) no N(1) C(5) C(4) C(3) . . . . 51.0(9) no N(1) C(5) C(6) C(7) . . . . -35.7(9) no N(1) C(8) C(7) C(6) . . . . -19.1(9) no C(1) N(1) C(5) C(4) . . . . -16(1) no C(1) N(1) C(5) C(6) . . . . -138.8(9) no C(1) N(1) C(5) C(15) . . . . 105(1) no C(1) N(1) C(8) C(7) . . . . 160.5(8) no C(1) N(1) C(8) C(16) . . . . -77(1) no C(1) C(2) C(3) C(4) . . . . 42(1) no C(2) C(1) N(1) C(5) . . . . -6(1) no C(2) C(1) N(1) C(8) . . . . -167.8(8) no C(2) C(3) C(4) C(5) . . . . -64.0(9) no C(3) C(4) C(5) C(6) . . . . 163.9(8) no C(3) C(4) C(5) C(15) . . . . -69.3(9) no C(4) O(2) Si(1) C(9) . . . . 76.4(7) no C(4) O(2) Si(1) C(10) . . . . -43.9(8) no C(4) O(2) Si(1) C(11) . . . . -165.5(6) no C(4) C(5) N(1) C(8) . . . . 147.1(7) no C(4) C(5) C(6) C(7) . . . . -154.4(7) no C(5) N(1) C(8) C(7) . . . . -4(1) no C(5) N(1) C(8) C(16) . . . . 118.8(8) no C(5) C(6) C(7) C(8) . . . . 35.0(9) no C(6) C(5) N(1) C(8) . . . . 24.6(9) no C(6) C(7) C(8) C(16) . . . . -137.9(8) no C(7) C(6) C(5) C(15) . . . . 78.6(9) no C(8) N(1) C(5) C(15) . . . . -91.1(9) no C(9) Si(1) C(11) C(12) . . . . 60.7(9) no C(9) Si(1) C(11) C(13) . . . . -58.4(9) no C(9) Si(1) C(11) C(14) . . . . -177.3(8) no C(10) Si(1) C(11) C(12) . . . . -176.7(9) no C(10) Si(1) C(11) C(13) . . . . 64.1(9) no C(10) Si(1) C(11) C(14) . . . . -54.8(9) no data_General _journal_coden_Cambridge 207 _publ_requested_journal 'Perkin Transactions 1' loop_ _publ_author_name 'Burnell, D. Jean' 'Elliott, Christine E.' 'Miller, David O.' _publ_contact_author_name 'Dr D. Jean Burnell' _publ_contact_author_address ; Department of Chemistry Memorial University of Newfoundland Department of Chemistry St. John's Newfoundland A1B 3X7 CANADA ; _publ_contact_author_email 'JBURNELL@MUN.CA' _publ_section_title ; Synthesis of 6-alkyl analogues of the 1-azabicyclo[4.3.0]nonan-2-one system by a strategy of geminal acylation and Beckmann rearrangement ; #============================================================================== _audit_creation_date '1999-11-10' _audit_creation_method 'by teXsan for Windows v1.0' _audit_update_record ; ? ; #============================================================================== _publ_section_references ; ENTER OTHER REFERENCES Molecular Structure Corporation. (1997-1998). teXsan for Windows version 1.03. Single Crystal Structure Analysis Software. Version 1.04. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. North, A.C.T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359. Sheldrick, G.M. (1997). ; #============================================================================== data__CEE97e-1_________________ _database_code_CSD 174417 #============================================================================== _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan for Windows (MSC, 1997)' _computing_structure_solution ; SHELX97 (Sheldrick, 1997) ; _computing_structure_refinement 'teXsan for Windows (MSC, 1997)' _computing_publication_material 'teXsan for Windows (MSC, 1997)' #------------------------------------------------------------------------------ _cell_length_a 20.714(1) _cell_length_b 6.033(1) _cell_length_c 21.606(1) _cell_angle_alpha 90 _cell_angle_beta 90.0(5) _cell_angle_gamma 90 _cell_volume 2699.9(4) _cell_formula_units_Z 8 _cell_measurement_temperature 299.2 _cell_measurement_reflns_used 24 _cell_measurement_theta_min 24.3 _cell_measurement_theta_max 29.9 #------------------------------------------------------------------------------ _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P c a 21 ' _symmetry_Int_Tables_number 29 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' ' -x, -y,1/2+z' '1/2-x, +y,1/2+z' '1/2+x, -y, +z' #------------------------------------------------------------------------------ _publ_section_exptl_prep ; ENTER EXPERIMENTAL SECTION ; _exptl_crystal_description 'plate' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.168 _exptl_crystal_density_meas 'not measured' _chemical_formula_weight 237.34 _chemical_formula_analytical ? _chemical_formula_sum 'C14 H23 N O2 ' _chemical_formula_moiety '?' _chemical_formula_structural ? _chemical_compound_source ? _exptl_crystal_F_000 1040.00 _exptl_absorpt_coefficient_mu 0.610 _exptl_absorpt_correction_type ; \y scans (North,Phillips & Matthews, 1968) ; _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.796 _exptl_special_details ; The scan width was (1.57+0.14tan\q)\% with an \w scan speed of 4\% per minute (up to 6 scans to achieve I/\s(I) > 10). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1. ; #============================================================================== # EXPERIMENTAL DATA _diffrn_special_details ; ? ; _diffrn_ambient_temperature 299.2 _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device 'Rigaku AFC6S' _diffrn_measurement_method \w-2\q _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% 0.68 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -4 -1 -5 2 0 -6 -2 0 -6 _diffrn_reflns_number 2372 _reflns_number_total 2372 _reflns_number_gt 1540 _reflns_threshold_expression I>2.00\s(I) _diffrn_reflns_av_R_equivalents 0.00000 _diffrn_reflns_av_sigmaI/netI 0.081 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 2.95 _diffrn_reflns_theta_max 60.07 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 -0.01992 _diffrn_orient_matrix_UB_12 -0.00654 _diffrn_orient_matrix_UB_13 -0.04212 _diffrn_orient_matrix_UB_21 0.04380 _diffrn_orient_matrix_UB_22 0.01184 _diffrn_orient_matrix_UB_23 -0.01918 _diffrn_orient_matrix_UB_31 0.00393 _diffrn_orient_matrix_UB_32 -0.16521 _diffrn_orient_matrix_UB_33 0.00029 #------------------------------------------------------------------------------ loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 112 0.017 0.009 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; H 0 184 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; N 0 8 0.029 0.018 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; O 0 16 0.047 0.032 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_refinement_flags _atom_site_adp_type _atom_site_calc_flag _atom_site_calc_attached_atom O(1) 0.4314(2) 0.8288(9) 0.0822 0.071(2) 1.000 . Uani d ? O(2) 0.5667(2) 0.1216(9) 0.0072(3) 0.073(2) 1.000 . Uani d ? O(3) 0.3267(2) 0.6918(9) -0.0420(2) 0.076(2) 1.000 . Uani d ? O(4) 0.1910(2) 1.391(1) 0.0413(3) 0.078(2) 1.000 . Uani d ? N(1) 0.4487(2) 0.542(1) 0.0138(3) 0.048(2) 1.000 . Uani d ? N(2) 0.3088(2) 0.961(1) 0.0302(4) 0.057(2) 1.000 . Uani d ? C(1) 0.4656(3) 0.674(1) 0.0615(4) 0.057(2) 1.000 . Uani d ? C(2) 0.5318(3) 0.618(2) 0.0895(4) 0.064(3) 1.000 . Uani d ? C(3) 0.5416(4) 0.373(2) 0.0873(4) 0.070(3) 1.000 . Uani d ? C(4) 0.5353(3) 0.280(1) 0.0233(4) 0.053(2) 1.000 . Uani d ? C(5) 0.4893(3) 0.398(1) -0.0203(4) 0.043(2) 1.000 . Uani d ? C(6) 0.4455(3) 0.235(1) -0.0562(4) 0.048(2) 1.000 . Uani d ? C(7) 0.4796(3) 0.105(1) -0.1075(4) 0.053(2) 1.000 . Uani d ? C(8) 0.5144(3) 0.258(1) -0.1537(4) 0.045(2) 1.000 . Uani d ? C(9) 0.5624(3) 0.393(1) -0.1172(4) 0.047(2) 1.000 . Uani d ? C(10) 0.5301(3) 0.5246(9) -0.0682(4) 0.034(2) 1.000 . Uani d ? C(11) 0.5455(3) 0.136(1) -0.2107(4) 0.062(2) 1.000 . Uani d ? C(12) 0.4965(5) -0.013(2) -0.2412(5) 0.088(4) 1.000 . Uani d ? C(13) 0.5663(4) 0.309(2) -0.2581(4) 0.089(3) 1.000 . Uani d ? C(14) 0.6042(4) -0.000(1) -0.1960(5) 0.077(3) 1.000 . Uani d ? C(15) 0.2920(3) 0.839(1) -0.0199(4) 0.057(2) 1.000 . Uani d ? C(16) 0.2267(3) 0.892(1) -0.0466(4) 0.060(2) 1.000 . Uani d ? C(17) 0.2159(3) 1.135(1) -0.0422(4) 0.062(2) 1.000 . Uani d ? C(18) 0.2196(3) 1.224(1) 0.0238(4) 0.051(2) 1.000 . Uani d ? C(19) 0.2659(3) 1.096(1) 0.0676(4) 0.042(2) 1.000 . Uani d ? C(20) 0.2279(3) 0.958(1) 0.1113(5) 0.056(2) 1.000 . Uani d ? C(21) 0.1922(3) 1.077(1) 0.1620(4) 0.050(2) 1.000 . Uani d ? C(22) 0.2394(3) 1.224(1) 0.2004(4) 0.043(2) 1.000 . Uani d ? C(23) 0.2753(3) 1.385(1) 0.1562(4) 0.050(2) 1.000 . Uani d ? C(24) 0.3091(3) 1.252(1) 0.1041(4) 0.056(2) 1.000 . Uani d ? C(25) 0.2077(3) 1.344(1) 0.2574(4) 0.051(2) 1.000 . Uani d ? C(26) 0.2573(4) 1.496(1) 0.2893(4) 0.060(3) 1.000 . Uani d ? C(27) 0.1872(3) 1.162(1) 0.3034(4) 0.067(2) 1.000 . Uani d ? C(28) 0.1498(3) 1.486(1) 0.2346(4) 0.055(2) 1.000 . Uani d ? H(1) 0.5648 0.6913 0.0653 0.079 1.000 . Uiso c ? H(2) 0.5338 0.6730 0.1305 0.079 1.000 . Uiso c ? H(3) 0.5830 0.3346 0.1028 0.088 1.000 . Uiso c ? H(4) 0.5095 0.3019 0.1131 0.088 1.000 . Uiso c ? H(5) 0.4285 0.1313 -0.0269 0.063 1.000 . Uiso c ? H(6) 0.4114 0.3169 -0.0738 0.063 1.000 . Uiso c ? H(7) 0.5104 0.0083 -0.0889 0.063 1.000 . Uiso c ? H(8) 0.4483 0.0204 -0.1288 0.063 1.000 . Uiso c ? H(9) 0.4830 0.3602 -0.1687 0.058 1.000 . Uiso c ? H(10) 0.5924 0.2950 -0.0974 0.055 1.000 . Uiso c ? H(11) 0.5849 0.4894 -0.1439 0.055 1.000 . Uiso c ? H(12) 0.5032 0.6293 -0.0887 0.046 1.000 . Uiso c ? H(13) 0.5634 0.6039 -0.0465 0.046 1.000 . Uiso c ? H(14) 0.4705 -0.0930 -0.2137 0.109 1.000 . Uiso c ? H(15) 0.4675 0.0749 -0.2680 0.109 1.000 . Uiso c ? H(16) 0.5176 -0.1163 -0.2691 0.109 1.000 . Uiso c ? H(17) 0.5837 0.4353 -0.2368 0.107 1.000 . Uiso c ? H(18) 0.5985 0.2475 -0.2837 0.107 1.000 . Uiso c ? H(19) 0.5304 0.3540 -0.2819 0.107 1.000 . Uiso c ? H(20) 0.6083 -0.0081 -0.1482 0.114 1.000 . Uiso c ? H(21) 0.6022 -0.1431 -0.2090 0.114 1.000 . Uiso c ? H(22) 0.6427 0.0733 -0.2078 0.114 1.000 . Uiso c ? H(23) 0.2246 0.8464 -0.0887 0.071 1.000 . Uiso c ? H(24) 0.1939 0.8172 -0.0237 0.071 1.000 . Uiso c ? H(25) 0.2483 1.2024 -0.0669 0.074 1.000 . Uiso c ? H(26) 0.1747 1.1636 -0.0593 0.074 1.000 . Uiso c ? H(27) 0.1968 0.8837 0.0870 0.057 1.000 . Uiso c ? H(28) 0.2565 0.8586 0.1298 0.057 1.000 . Uiso c ? H(29) 0.1584 1.1644 0.1454 0.065 1.000 . Uiso c ? H(30) 0.1733 0.9665 0.1890 0.065 1.000 . Uiso c ? H(31) 0.2710 1.1293 0.2174 0.053 1.000 . Uiso c ? H(32) 0.2446 1.4868 0.1391 0.062 1.000 . Uiso c ? H(33) 0.3061 1.4684 0.1799 0.062 1.000 . Uiso c ? H(34) 0.3429 1.1687 0.1230 0.067 1.000 . Uiso c ? H(35) 0.3273 1.3563 0.0762 0.067 1.000 . Uiso c ? H(36) 0.2528 1.4811 0.3318 0.073 1.000 . Uiso c ? H(37) 0.2983 1.4520 0.2753 0.073 1.000 . Uiso c ? H(38) 0.2485 1.6441 0.2764 0.073 1.000 . Uiso c ? H(39) 0.1910 1.2088 0.3452 0.083 1.000 . Uiso c ? H(40) 0.1437 1.1155 0.2960 0.083 1.000 . Uiso c ? H(41) 0.2146 1.0329 0.2979 0.083 1.000 . Uiso c ? H(42) 0.1289 1.5446 0.2737 0.058 1.000 . Uiso c ? H(43) 0.1652 1.6086 0.2135 0.058 1.000 . Uiso c ? H(44) 0.1211 1.4008 0.2147 0.058 1.000 . Uiso c ? H(46) 0.3435 0.9169 0.0489 0.069 1.000 . Uiso c ? H(45) 0.4045 0.5601 -0.0008 0.056 1.000 . Uiso c ? loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O(1) 0.061(3) 0.102(4) 0.051(3) 0.036(3) -0.011(2) -0.022(3) O(2) 0.081(4) 0.064(3) 0.073(4) 0.028(3) -0.003(3) 0.012(3) O(3) 0.059(3) 0.093(4) 0.074(3) 0.039(3) -0.012(3) -0.037(3) O(4) 0.080(3) 0.097(4) 0.058(3) 0.044(3) -0.004(3) -0.003(3) N(1) 0.026(2) 0.080(4) 0.037(3) 0.007(3) -0.005(2) -0.005(3) N(2) 0.026(2) 0.088(5) 0.056(4) 0.014(3) -0.007(3) -0.019(4) C(1) 0.043(4) 0.087(6) 0.041(4) 0.006(4) 0.001(3) 0.006(4) C(2) 0.041(4) 0.098(7) 0.051(5) 0.008(5) -0.009(3) -0.007(5) C(3) 0.072(5) 0.096(7) 0.043(5) 0.011(5) -0.014(4) -0.006(5) C(4) 0.047(4) 0.066(5) 0.048(4) 0.007(4) 0.005(3) 0.019(4) C(5) 0.040(3) 0.040(4) 0.048(4) 0.005(3) -0.007(3) 0.004(3) C(6) 0.043(3) 0.049(4) 0.052(4) -0.004(3) 0.011(3) 0.003(3) C(7) 0.047(4) 0.039(4) 0.072(5) -0.014(3) -0.002(4) -0.007(4) C(8) 0.036(3) 0.053(4) 0.045(4) 0.005(3) 0.001(3) -0.002(3) C(9) 0.057(4) 0.032(3) 0.052(4) -0.016(3) 0.012(3) 0.002(3) C(10) 0.040(3) 0.045(4) 0.017(3) -0.001(3) -0.002(3) 0.003(3) C(11) 0.048(4) 0.092(6) 0.047(4) 0.012(4) -0.001(3) -0.015(4) C(12) 0.063(5) 0.098(8) 0.104(9) 0.003(5) -0.002(6) -0.047(6) C(13) 0.079(6) 0.138(9) 0.049(5) -0.000(6) 0.003(4) 0.003(5) C(14) 0.063(5) 0.097(8) 0.070(6) 0.028(4) 0.017(5) -0.003(5) C(15) 0.044(4) 0.081(5) 0.045(4) 0.006(4) -0.004(3) -0.001(4) C(16) 0.041(4) 0.098(6) 0.042(4) 0.032(4) -0.010(3) -0.032(4) C(17) 0.057(4) 0.092(7) 0.037(4) 0.017(5) -0.013(4) 0.016(4) C(18) 0.043(4) 0.056(4) 0.053(4) 0.011(3) 0.008(3) 0.010(4) C(19) 0.037(3) 0.046(4) 0.042(4) 0.007(3) -0.005(3) -0.002(3) C(20) 0.040(4) 0.059(4) 0.069(6) -0.006(4) -0.004(4) 0.002(4) C(21) 0.040(3) 0.067(4) 0.042(4) -0.009(4) -0.006(3) 0.002(4) C(22) 0.037(3) 0.044(4) 0.049(4) 0.001(3) -0.008(3) -0.000(3) C(23) 0.048(4) 0.055(4) 0.047(4) -0.004(4) 0.005(3) -0.006(4) C(24) 0.043(4) 0.058(5) 0.068(5) -0.006(4) 0.001(3) -0.006(4) C(25) 0.063(4) 0.041(4) 0.049(4) 0.001(3) 0.004(3) -0.004(3) C(26) 0.067(5) 0.066(6) 0.046(5) -0.002(4) -0.002(4) -0.026(4) C(27) 0.061(4) 0.097(6) 0.044(4) -0.012(5) 0.007(4) -0.009(4) C(28) 0.040(4) 0.071(6) 0.055(5) 0.008(3) 0.011(4) -0.004(4) #============================================================================== # REFINEMENT DATA _refine_special_details ; ? ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme sigma _refine_ls_weighting_details 'w = 1/[\s^2^(Fo) + 0.00010|Fo|^2^]' _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1540 _refine_ls_number_parameters 306 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.1332 _refine_ls_R_factor_gt 0.0940 _refine_ls_wR_factor_all 0.1110 _refine_ls_wR_factor_ref 0.1080 _refine_ls_goodness_of_fit_all 3.464 _refine_ls_goodness_of_fit_ref 4.030 _refine_ls_shift/su_max 0.0100 _refine_ls_shift/su_mean 0.0010 _refine_diff_density_min -0.25 _refine_diff_density_max 0.00 #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O(1) C(1) 1.25(2) . . ? O(2) C(4) 1.21(2) . . ? O(3) C(15) 1.24(2) . . ? O(4) C(18) 1.23(1) . . ? N(1) C(1) 1.35(2) . . ? N(1) C(5) 1.42(2) . . ? N(1) H(45) 0.97 . . no N(2) C(15) 1.35(2) . . ? N(2) C(19) 1.45(2) . . ? N(2) H(46) 0.87 . . no C(1) C(2) 1.54(2) . . ? C(2) C(3) 1.49(3) . . ? C(2) H(1) 0.97 . . no C(2) H(2) 0.95 . . no C(3) C(4) 1.50(2) . . ? C(3) H(3) 0.95 . . no C(3) H(4) 0.97 . . no C(4) C(5) 1.52(2) . . ? C(5) C(6) 1.55(2) . . ? C(5) C(10) 1.54(2) . . ? C(6) C(7) 1.53(2) . . ? C(6) H(5) 0.96 . . no C(6) H(6) 0.94 . . no C(7) C(8) 1.54(2) . . ? C(7) H(7) 0.95 . . no C(7) H(8) 0.94 . . no C(8) C(9) 1.51(2) . . ? C(8) C(11) 1.57(2) . . ? C(8) H(9) 0.95 . . no C(9) C(10) 1.48(2) . . ? C(9) H(10) 0.96 . . no C(9) H(11) 0.94 . . no C(10) H(12) 0.95 . . no C(10) H(13) 0.96 . . no C(11) C(12) 1.51(2) . . ? C(11) C(13) 1.52(2) . . ? C(11) C(14) 1.50(2) . . ? C(12) H(14) 0.94 . . no C(12) H(15) 0.99 . . no C(12) H(16) 0.97 . . no C(13) H(17) 0.96 . . no C(13) H(18) 0.94 . . no C(13) H(19) 0.94 . . no C(14) H(20) 1.04 . . no C(14) H(21) 0.91 . . no C(14) H(22) 0.95 . . no C(15) C(16) 1.50(2) . . ? C(16) C(17) 1.49(2) . . ? C(16) H(23) 0.95 . . no C(16) H(24) 0.95 . . no C(17) C(18) 1.53(2) . . ? C(17) H(25) 0.95 . . no C(17) H(26) 0.94 . . no C(18) C(19) 1.55(2) . . ? C(19) C(20) 1.48(2) . . ? C(19) C(24) 1.52(2) . . ? C(20) C(21) 1.50(2) . . ? C(20) H(27) 0.94 . . no C(20) H(28) 0.93 . . no C(21) C(22) 1.56(2) . . ? C(21) H(29) 0.95 . . no C(21) H(30) 0.97 . . no C(22) C(23) 1.55(2) . . ? C(22) C(25) 1.57(2) . . ? C(22) H(31) 0.94 . . no C(23) C(24) 1.55(2) . . ? C(23) H(32) 0.96 . . no C(23) H(33) 0.96 . . no C(24) H(34) 0.95 . . no C(24) H(35) 0.95 . . no C(25) C(26) 1.54(2) . . ? C(25) C(27) 1.54(2) . . ? C(25) C(28) 1.56(2) . . ? C(26) H(36) 0.93 . . no C(26) H(37) 0.94 . . no C(26) H(38) 0.95 . . no C(27) H(39) 0.95 . . no C(27) H(40) 0.96 . . no C(27) H(41) 0.97 . . no C(28) H(42) 1.01 . . no C(28) H(43) 0.92 . . no C(28) H(44) 0.90 . . no #------------------------------------------------------------------------------ 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C(1) N(1) C(5) 127(1) . . . ? C(1) N(1) H(45) 115.2 . . . no C(5) N(1) H(45) 117.2 . . . no C(15) N(2) C(19) 126(1) . . . ? C(15) N(2) H(46) 114.7 . . . no C(19) N(2) H(46) 114.9 . . . no O(1) C(1) N(1) 124(1) . . . ? O(1) C(1) C(2) 122(1) . . . ? N(1) C(1) C(2) 114(1) . . . ? C(1) C(2) C(3) 109(1) . . . ? C(1) C(2) H(1) 108.3 . . . no C(1) C(2) H(2) 109.2 . . . no C(3) C(2) H(1) 109.8 . . . no C(3) C(2) H(2) 111.8 . . . no H(1) C(2) H(2) 108.4 . . . no C(2) C(3) C(4) 113(1) . . . ? C(2) C(3) H(3) 110.8 . . . no C(2) C(3) H(4) 109.1 . . . no C(4) C(3) H(3) 108.2 . . . no C(4) C(3) H(4) 107.7 . . . no H(3) C(3) H(4) 108.0 . . . no O(2) C(4) C(3) 121(1) . . . ? O(2) C(4) C(5) 122(1) . . . ? C(3) C(4) C(5) 117(1) . . . ? N(1) C(5) C(4) 110(1) . . . ? N(1) C(5) C(6) 107.7(9) . . . ? N(1) C(5) C(10) 112(1) . . . ? C(4) C(5) C(6) 113(1) . . . ? C(4) C(5) C(10) 108(1) . . . ? C(6) C(5) C(10) 108(1) . . . ? C(5) C(6) C(7) 115(1) . . . ? C(5) C(6) H(5) 107.3 . . . no C(5) C(6) H(6) 107.8 . . . no C(7) C(6) H(5) 108.4 . . . no C(7) C(6) H(6) 108.9 . . . no H(5) C(6) H(6) 109.6 . . . no C(6) C(7) C(8) 112(1) . . . ? C(6) C(7) H(7) 108.5 . . . no C(6) C(7) H(8) 108.2 . . . no C(8) C(7) H(7) 109.1 . . . no C(8) C(7) H(8) 109.1 . . . no H(7) C(7) H(8) 109.8 . . . no C(7) C(8) C(9) 107(1) . . . ? C(7) C(8) C(11) 115(1) . . . ? C(7) C(8) H(9) 106.8 . . . no C(9) C(8) C(11) 113(1) . . . ? C(9) C(8) H(9) 106.3 . . . no C(11) C(8) H(9) 108.6 . . . no C(8) C(9) C(10) 111(1) . . . ? C(8) C(9) H(10) 109.2 . . . no C(8) C(9) H(11) 109.9 . . . no C(10) C(9) H(10) 107.6 . . . no C(10) C(9) H(11) 109.2 . . . no H(10) C(9) H(11) 109.5 . . . no C(5) C(10) C(9) 117(1) . . . ? C(5) C(10) H(12) 108.7 . . . no C(5) C(10) H(13) 108.3 . . . no C(9) C(10) H(12) 106.7 . . . no C(9) C(10) H(13) 106.9 . . . no H(12) C(10) H(13) 108.5 . . . no C(8) C(11) C(12) 110(1) . . . ? C(8) C(11) C(13) 109(1) . . . ? C(8) C(11) C(14) 115(1) . . . ? C(12) C(11) C(13) 108(2) . . . ? C(12) C(11) C(14) 108(1) . . . ? C(13) C(11) C(14) 107(1) . . . ? C(11) C(12) H(14) 114.6 . . . no C(11) C(12) H(15) 110.1 . . . no C(11) C(12) H(16) 110.6 . . . no H(14) C(12) H(15) 107.3 . . . no H(14) C(12) H(16) 109.1 . . . no H(15) C(12) H(16) 104.7 . . . no C(11) C(13) H(17) 109.2 . . . no C(11) C(13) H(18) 109.0 . . . no C(11) C(13) H(19) 110.0 . . . no H(17) C(13) H(18) 109.0 . . . no H(17) C(13) H(19) 109.0 . . . no H(18) C(13) H(19) 110.6 . . . no C(11) C(14) H(20) 107.6 . . . no C(11) C(14) H(21) 114.6 . . . no C(11) C(14) H(22) 111.8 . . . no H(20) C(14) H(21) 105.5 . . . no H(20) C(14) H(22) 102.7 . . . no H(21) C(14) H(22) 113.5 . . . no O(3) C(15) N(2) 123(1) . . . ? O(3) C(15) C(16) 122(1) . . . ? N(2) C(15) C(16) 115(1) . . . ? C(15) C(16) C(17) 108(1) . . . ? C(15) C(16) H(23) 110.4 . . . no C(15) C(16) H(24) 110.0 . . . no C(17) C(16) H(23) 109.7 . . . no C(17) C(16) H(24) 109.0 . . . no H(23) C(16) H(24) 109.2 . . . no C(16) C(17) C(18) 113(1) . . . ? C(16) C(17) H(25) 106.1 . . . no C(16) C(17) H(26) 106.8 . . . no C(18) C(17) H(25) 109.9 . . . no C(18) C(17) H(26) 110.3 . . . no H(25) C(17) H(26) 110.1 . . . no O(4) C(18) C(17) 124(1) . . . ? O(4) C(18) C(19) 121(1) . . . ? C(17) C(18) C(19) 115(1) . . . ? N(2) C(19) C(18) 109(1) . . . ? N(2) C(19) C(20) 111(1) . . . ? N(2) C(19) C(24) 106(1) . . . ? C(18) C(19) C(20) 110(1) . . . ? C(18) C(19) C(24) 112(1) . . . ? C(20) C(19) C(24) 109(1) . . . ? C(19) C(20) C(21) 117(1) . . . ? C(19) C(20) H(27) 105.9 . . . no C(19) C(20) H(28) 107.4 . . . no C(21) C(20) H(27) 107.2 . . . no C(21) C(20) H(28) 107.9 . . . no H(27) C(20) H(28) 111.4 . . . no C(20) C(21) C(22) 110(1) . . . ? C(20) C(21) H(29) 110.6 . . . no C(20) C(21) H(30) 107.9 . . . no C(22) C(21) H(29) 110.5 . . . no C(22) C(21) H(30) 109.0 . . . no H(29) C(21) H(30) 108.3 . . . no C(21) C(22) C(23) 109(1) . . . ? C(21) C(22) C(25) 115(1) . . . ? C(21) C(22) H(31) 107.4 . . . no C(23) C(22) C(25) 113(1) . . . ? C(23) C(22) H(31) 106.6 . . . no C(25) C(22) H(31) 105.2 . . . no C(22) C(23) C(24) 110(1) . . . ? C(22) C(23) H(32) 108.7 . . . no C(22) C(23) H(33) 108.7 . . . no C(24) C(23) H(32) 110.5 . . . no C(24) C(23) H(33) 111.0 . . . no H(32) C(23) H(33) 108.0 . . . no C(19) C(24) C(23) 116(1) . . . ? C(19) C(24) H(34) 109.3 . . . no C(19) C(24) H(35) 108.3 . . . no C(23) C(24) H(34) 107.0 . . . no C(23) C(24) H(35) 107.3 . . . no H(34) C(24) H(35) 109.1 . . . no C(22) C(25) C(26) 110(1) . . . ? C(22) C(25) C(27) 107(1) . . . ? C(22) C(25) C(28) 109(1) . . . ? C(26) C(25) C(27) 109(1) . . . ? C(26) C(25) C(28) 109(1) . . . ? C(27) C(25) C(28) 113(1) . . . ? C(25) C(26) H(36) 108.6 . . . no C(25) C(26) H(37) 106.8 . . . no C(25) C(26) H(38) 107.5 . . . no H(36) C(26) H(37) 112.4 . . . no H(36) C(26) H(38) 111.2 . . . no H(37) C(26) H(38) 110.1 . . . no C(25) C(27) H(39) 112.4 . . . no C(25) C(27) H(40) 111.2 . . . no C(25) C(27) H(41) 109.3 . . . no H(39) C(27) H(40) 109.0 . . . no H(39) C(27) H(41) 107.7 . . . no H(40) C(27) H(41) 106.9 . . . no C(25) C(28) H(42) 104.8 . . . no C(25) C(28) H(43) 109.3 . . . no C(25) C(28) H(44) 110.3 . . . no H(42) C(28) H(43) 106.3 . . . no H(42) C(28) H(44) 108.5 . . . no H(43) C(28) H(44) 116.8 . . . no #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O(1) N(2) 2.89(2) . . no O(1) O(3) 3.55(2) . . no O(1) C(13) 3.55(2) . 2_665 no O(2) C(16) 3.51(2) . 4_565 no O(2) C(2) 3.59(2) . 1_545 no O(3) N(1) 2.94(2) . . no O(4) C(2) 3.46(2) . 4_475 no O(4) C(3) 3.55(2) . 4_475 no #------------------------------------------------------------------------------ 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag O(1) C(1) N(1) C(5) . . . . 166(1) no O(1) C(1) C(2) C(3) . . . . 144(1) no O(2) C(4) C(3) C(2) . . . . 148(1) no O(2) C(4) C(5) N(1) . . . . 167(1) no O(2) C(4) C(5) C(6) . . . . 47(2) no O(2) C(4) C(5) C(10) . . . . -72(2) no O(3) C(15) N(2) C(19) . . . . -164(1) no O(3) C(15) C(16) C(17) . . . . -144(1) no O(4) C(18) C(17) C(16) . . . . -153(1) no O(4) C(18) C(19) N(2) . . . . -160(1) no O(4) C(18) C(19) C(20) . . . . 78(2) no O(4) C(18) C(19) C(24) . . . . -44(2) no N(1) C(1) C(2) C(3) . . . . -35(2) no N(1) C(5) C(4) C(3) . . . . -15(2) no N(1) C(5) C(6) C(7) . . . . 166(1) no N(1) C(5) C(10) C(9) . . . . -165(1) no N(2) C(15) C(16) C(17) . . . . 37(2) no N(2) C(19) C(18) C(17) . . . . 17(2) no N(2) C(19) C(20) C(21) . . . . 167(1) no N(2) C(19) C(24) C(23) . . . . -170(1) no C(1) N(1) C(5) C(4) . . . . 41(2) no C(1) N(1) C(5) C(6) . . . . 164(1) no C(1) N(1) C(5) C(10) . . . . -79(2) no C(1) C(2) C(3) C(4) . . . . 56(2) no C(2) C(1) N(1) C(5) . . . . -15(2) no C(2) C(3) C(4) C(5) . . . . -31(2) no C(3) C(4) C(5) C(6) . . . . -135(1) no C(3) C(4) C(5) C(10) . . . . 107(1) no C(4) C(5) C(6) C(7) . . . . -73(2) no C(4) C(5) C(10) C(9) . . . . 74(1) no C(5) C(6) C(7) C(8) . . . . -54(2) no C(5) C(10) C(9) C(8) . . . . 57(1) no C(6) C(5) C(10) C(9) . . . . -47(1) no C(6) C(7) C(8) C(9) . . . . 59(1) no C(6) C(7) C(8) C(11) . . . . -175(1) no C(7) C(6) C(5) C(10) . . . . 45(1) no C(7) C(8) C(9) C(10) . . . . -59(1) no C(7) C(8) C(11) C(12) . . . . 51(2) no C(7) C(8) C(11) C(13) . . . . 169(1) no C(7) C(8) C(11) C(14) . . . . -71(2) no C(9) C(8) C(11) C(12) . . . . 174(1) no C(9) C(8) C(11) C(13) . . . . -68(1) no C(9) C(8) C(11) C(14) . . . . 52(2) no C(10) C(9) C(8) C(11) . . . . 174(1) no C(15) N(2) C(19) C(18) . . . . -42(2) no C(15) N(2) C(19) C(20) . . . . 79(2) no C(15) N(2) C(19) C(24) . . . . -163(1) no C(15) C(16) C(17) C(18) . . . . -58(2) no C(16) C(15) N(2) C(19) . . . . 15(2) no C(16) C(17) C(18) C(19) . . . . 31(2) no C(17) C(18) C(19) C(20) . . . . -105(1) no C(17) C(18) C(19) C(24) . . . . 133(1) no C(18) C(19) C(20) C(21) . . . . -72(2) no C(18) C(19) C(24) C(23) . . . . 72(2) no C(19) C(20) C(21) C(22) . . . . -55(2) no C(19) C(24) C(23) C(22) . . . . 54(2) no C(20) C(19) C(24) C(23) . . . . -50(2) no C(20) C(21) C(22) C(23) . . . . 56(2) no C(20) C(21) C(22) C(25) . . . . -176(1) no C(21) C(20) C(19) C(24) . . . . 51(2) no C(21) C(22) C(23) C(24) . . . . -55(1) no C(21) C(22) C(25) C(26) . . . . -176(1) no C(21) C(22) C(25) C(27) . . . . 66(1) no C(21) C(22) C(25) C(28) . . . . -56(1) no C(23) C(22) C(25) C(26) . . . . -50(2) no C(23) C(22) C(25) C(27) . . . . -168(1) no C(23) C(22) C(25) C(28) . . . . 70(1) no C(24) C(23) C(22) C(25) . . . . 176(1) no #------------------------------------------------------------------------------ #============================================================================== # End of CIF #==============================================================================