# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 207/412 data_S504/1 #------------------------------------------------------------------------------ _audit_creation_date '1997-02-07' _audit_creation_method 'by teXsan v1.7' _audit_update_record ; ? ; #------------------------------------------------------------------------------ _publ_requested_journal ' ENTER JOURNAL NAME HERE' _publ_contact_author ; ENTER NAME ENTER ADDRESS ; _publ_contact_letter ; ENTER TEXT OF LETTER ; _publ_requested_coeditor_name ? _publ_contact_author_phone ' ENTER PHONE NUMBER ' _publ_contact_author_fax ' ENTER FAX NUMBER ' _publ_contact_author_email ' ENTER EMAIL ADDRESS ' loop_ _publ_author_name _publ_author_address ' FIRST AUTHORS NAME ' ; FIRST AUTHORS ADDRESS ; _publ_section_title ; ENTER SECTION TITLE ; _publ_section_abstract ; ENTER ABSTRACT ; _publ_section_exptl_prep ; ENTER EXPERIMENTAL SECTION ; _publ_section_exptl_refinement ; ENTER EXPERIMENTAL SECTION ; _publ_section_comment ; ENTER TEXT ; _publ_section_references ; ENTER OTHER REFERENCES Molecular Structure Corporation. (1995). teXsan. Single Crystal Structure Analysis Software. Version 1.7. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. Altomare, A., Cascarano, M., Giacovazzo, C., Guagliardi, A. (1993). J. Appl. Cryst., 26, 343. ; _publ_section_acknowledgements ; ENTER ACKNOWLEDGEMENTS ; _publ_section_table_legends ; ENTER TABLE LEGENDS ; _publ_section_figure_captions ; ENTER FIGURE CAPTIONS ; #------------------------------------------------------------------------------ _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan (MSC, 1995)' _computing_structure_solution ; SIR92 (Altomare, et. al. 1993) ; _computing_structure_refinement 'teXsan (MSC, 1995)' _computing_publication_material 'teXsan (MSC, 1995)' #------------------------------------------------------------------------------ _cell_length_a 7.6743(9) _cell_length_b 24.817(4) _cell_length_c 10.629(1) _cell_angle_alpha 90 _cell_angle_beta 101.216(9) _cell_angle_gamma 90 _cell_volume 1985.6(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293.2 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10.0 _cell_measurement_theta_max 12.5 #------------------------------------------------------------------------------ _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n ' _symmetry_Int_Tables_number 14 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' '1/2-x,1/2+y,1/2-z' ' -x, -y, -z' '1/2+x,1/2-y,1/2+z' #------------------------------------------------------------------------------ _exptl_crystal_description 'prismatic' _exptl_crystal_colour 'colourlessprismatic' _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.25 _exptl_crystal_density_diffrn 1.202 _exptl_crystal_density_meas 'not measured' _chemical_formula_weight 359.47 _chemical_formula_analytical ? _chemical_formula_sum 'C24 H25 N O2 ' _chemical_formula_moiety 'C24 H25 N O2 ' _chemical_formula_structural ? _chemical_compound_source ? _exptl_crystal_F_000 768.00 _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_type none _exptl_special_details ; The scan width was (1.22+0.30tan\q)\% with an \w scan speed of 16\% per minute (up to 4 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. ; #------------------------------------------------------------------------------ _diffrn_special_details ; ? ; _diffrn_ambient_temperature 293.2 _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device 'Rigaku AFC5R' _diffrn_measurement_method \w _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% -0.40 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? ? ? ? ? ? ? _diffrn_reflns_number 3896 _reflns_number_total 3615 _reflns_number_observed 2252 _reflns_observed_criterion >3.00\s(I) _diffrn_reflns_av_R_equivalents 0.04876 _diffrn_reflns_av_sigmaI/netI ? _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 0.00 _diffrn_reflns_theta_max 25.05 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 0.01738 _diffrn_orient_matrix_UB_12 0.03995 _diffrn_orient_matrix_UB_13 0.00309 _diffrn_orient_matrix_UB_21 0.03437 _diffrn_orient_matrix_UB_22 -0.00166 _diffrn_orient_matrix_UB_23 0.09563 _diffrn_orient_matrix_UB_31 0.12714 _diffrn_orient_matrix_UB_32 -0.00502 _diffrn_orient_matrix_UB_33 -0.00678 #------------------------------------------------------------------------------ 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 96 0.003 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; H 0 100 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; N 0 4 0.006 0.003 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; O 0 8 0.011 0.006 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ 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_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom O(1) 0.0364(4) 0.71715(9) 0.3015(2) 0.0943(10) 1.000 . Uani d ? O(2) 0.0484(3) 0.59684(8) 0.3077(2) 0.0540(6) 1.000 . Uani d ? N(1) 0.3355(3) 0.6230(1) 0.3678(2) 0.0498(8) 1.000 . Uani d ? C(1) 0.1218(3) 0.6410(1) 0.5065(3) 0.0430(9) 1.000 . Uani d ? C(2) 0.0772(4) 0.6942(1) 0.5194(3) 0.0482(9) 1.000 . Uani d ? C(3) 0.0244(4) 0.7106(1) 0.6338(3) 0.056(1) 1.000 . Uani d ? C(4) 0.0173(4) 0.6754(1) 0.7296(3) 0.059(1) 1.000 . Uani d ? C(5) 0.0634(4) 0.6212(1) 0.7197(3) 0.0489(9) 1.000 . Uani d ? C(6) 0.0549(4) 0.5838(2) 0.8178(3) 0.062(1) 1.000 . Uani d ? C(7) 0.0974(5) 0.5316(2) 0.8046(3) 0.070(1) 1.000 . Uani d ? C(8) 0.1518(4) 0.5135(1) 0.6930(3) 0.065(1) 1.000 . Uani d ? C(9) 0.1609(4) 0.5486(1) 0.5975(3) 0.055(1) 1.000 . Uani d ? C(10) 0.1169(3) 0.6036(1) 0.6071(3) 0.0435(9) 1.000 . Uani d ? C(11) 0.0717(4) 0.7329(1) 0.4119(3) 0.057(1) 1.000 . Uani d ? C(12) 0.1044(4) 0.7915(1) 0.4368(3) 0.0489(10) 1.000 . Uani d ? C(13) 0.2197(4) 0.8108(1) 0.5438(3) 0.058(1) 1.000 . Uani d ? C(14) 0.2501(4) 0.8654(2) 0.5597(3) 0.066(1) 1.000 . Uani d ? C(15) 0.1638(5) 0.9007(1) 0.4693(4) 0.069(1) 1.000 . Uani d ? C(16) 0.0497(5) 0.8820(1) 0.3624(3) 0.065(1) 1.000 . Uani d ? C(17) 0.0209(4) 0.8278(1) 0.3458(3) 0.055(1) 1.000 . Uani d ? C(18) 0.1664(4) 0.6190(1) 0.3834(3) 0.0444(9) 1.000 . Uani d ? C(19) 0.4799(4) 0.6435(1) 0.4669(3) 0.056(1) 1.000 . Uani d ? C(20) 0.5535(5) 0.6966(2) 0.4297(4) 0.087(1) 1.000 . Uani d ? C(21) 0.6242(5) 0.6022(2) 0.5063(4) 0.086(1) 1.000 . Uani d ? C(22) 0.3808(4) 0.6062(2) 0.2442(3) 0.070(1) 1.000 . Uani d ? C(23) 0.2789(5) 0.6394(2) 0.1344(3) 0.093(2) 1.000 . Uani d ? C(24) 0.3635(5) 0.5461(2) 0.2219(4) 0.105(2) 1.000 . Uani d ? H(3) -0.0067 0.7473 0.6435 0.067 1.000 . Uiso c ? H(4) -0.0197 0.6876 0.8049 0.071 1.000 . Uiso c ? H(6) 0.0189 0.5953 0.8941 0.075 1.000 . Uiso c ? H(7) 0.0904 0.5068 0.8715 0.084 1.000 . Uiso c ? H(8) 0.1821 0.4767 0.6849 0.078 1.000 . Uiso c ? H(9) 0.1977 0.5361 0.5223 0.065 1.000 . Uiso c ? H(13) 0.2783 0.7863 0.6068 0.070 1.000 . Uiso c ? H(14) 0.3304 0.8784 0.6328 0.079 1.000 . Uiso c ? H(15) 0.1832 0.9383 0.4808 0.083 1.000 . Uiso c ? H(16) -0.0093 0.9067 0.3001 0.077 1.000 . Uiso c ? H(17) -0.0569 0.8149 0.2712 0.066 1.000 . Uiso c ? H(19) 0.4302 0.6505 0.5404 0.067 1.000 . Uiso c ? H(20A) 0.6430 0.7090 0.4982 0.105 1.000 . Uiso c ? H(20B) 0.4606 0.7224 0.4122 0.105 1.000 . Uiso c ? H(20C) 0.6031 0.6915 0.3553 0.105 1.000 . Uiso c ? H(21A) 0.6815 0.5952 0.4364 0.103 1.000 . Uiso c ? H(21B) 0.5734 0.5698 0.5304 0.103 1.000 . Uiso c ? H(21C) 0.7085 0.6155 0.5770 0.103 1.000 . Uiso c ? H(22) 0.5027 0.6147 0.2496 0.084 1.000 . Uiso c ? H(23A) 0.2824 0.6763 0.1584 0.112 1.000 . Uiso c ? H(23B) 0.1589 0.6275 0.1149 0.112 1.000 . Uiso c ? H(23C) 0.3314 0.6351 0.0611 0.112 1.000 . Uiso c ? H(24A) 0.2421 0.5361 0.2108 0.126 1.000 . Uiso c ? H(24B) 0.4076 0.5370 0.1471 0.126 1.000 . Uiso c ? H(24C) 0.4301 0.5277 0.2937 0.126 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) 0.165(3) 0.064(2) 0.044(1) 0.009(2) -0.004(2) -0.002(1) O(2) 0.050(1) 0.063(1) 0.046(1) -0.012(1) 0.0038(10) -0.009(1) N(1) 0.043(1) 0.065(2) 0.042(1) -0.009(1) 0.008(1) -0.010(1) C(1) 0.035(2) 0.052(2) 0.040(2) -0.003(1) 0.003(1) -0.005(1) C(2) 0.047(2) 0.054(2) 0.042(2) 0.004(1) 0.003(1) -0.002(2) C(3) 0.054(2) 0.059(2) 0.055(2) 0.009(2) 0.010(2) -0.009(2) C(4) 0.059(2) 0.073(2) 0.047(2) 0.001(2) 0.016(2) -0.011(2) C(5) 0.043(2) 0.060(2) 0.044(2) -0.004(2) 0.010(1) -0.004(2) C(6) 0.061(2) 0.079(3) 0.050(2) -0.011(2) 0.017(2) 0.001(2) C(7) 0.073(3) 0.076(3) 0.060(2) -0.016(2) 0.013(2) 0.015(2) C(8) 0.071(2) 0.057(2) 0.066(2) -0.007(2) 0.013(2) 0.007(2) C(9) 0.056(2) 0.057(2) 0.052(2) -0.006(2) 0.013(2) -0.002(2) C(10) 0.035(2) 0.052(2) 0.042(2) -0.005(1) 0.004(1) -0.003(1) C(11) 0.064(2) 0.063(2) 0.040(2) 0.011(2) 0.000(2) -0.003(2) C(12) 0.049(2) 0.054(2) 0.042(2) 0.003(2) 0.005(1) -0.001(1) C(13) 0.053(2) 0.069(2) 0.050(2) 0.003(2) 0.002(2) -0.001(2) C(14) 0.055(2) 0.084(3) 0.058(2) -0.016(2) 0.009(2) -0.015(2) C(15) 0.077(3) 0.060(2) 0.075(3) -0.014(2) 0.024(2) -0.007(2) C(16) 0.073(2) 0.061(2) 0.060(2) 0.000(2) 0.014(2) 0.008(2) C(17) 0.057(2) 0.060(2) 0.047(2) 0.003(2) 0.005(2) 0.001(2) C(18) 0.044(2) 0.046(2) 0.041(2) -0.004(1) 0.004(1) -0.001(1) C(19) 0.043(2) 0.073(2) 0.051(2) -0.008(2) 0.007(2) -0.009(2) C(20) 0.074(3) 0.089(3) 0.096(3) -0.030(2) 0.007(2) -0.004(2) C(21) 0.056(2) 0.108(3) 0.087(3) 0.006(2) -0.002(2) -0.001(2) C(22) 0.058(2) 0.104(3) 0.052(2) -0.016(2) 0.022(2) -0.022(2) C(23) 0.085(3) 0.154(4) 0.044(2) -0.030(3) 0.019(2) -0.006(2) C(24) 0.101(3) 0.108(3) 0.116(4) -0.011(3) 0.045(3) -0.056(3) #------------------------------------------------------------------------------ _refine_special_details ; ? ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme 'w = 1/[\s^2^(Fo) + 0.00002|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 2252 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all ? _refine_ls_R_factor_obs 0.0508 _refine_ls_wR_factor_all ? _refine_ls_wR_factor_obs 0.0502 _refine_ls_goodness_of_fit_all ? _refine_ls_goodness_of_fit_obs 2.574 _refine_ls_shift/esd_max 0.0009 _refine_ls_shift/esd_mean 0.0000 _refine_diff_density_min -0.20 _refine_diff_density_max 0.19 #------------------------------------------------------------------------------ _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 C11 1.216(4) . . yes O2 C18 1.219(3) . . yes N1 C18 1.344(4) . . yes N1 C19 1.463(4) . . yes N1 C22 1.483(4) . . yes C1 C2 1.377(4) . . yes C1 C10 1.421(4) . . yes C1 C18 1.517(4) . . yes C2 C3 1.414(4) . . yes C2 C11 1.488(4) . . yes C3 C4 1.352(5) . . yes C3 H3 0.95 . . no C4 C5 1.398(5) . . yes C4 H4 0.95 . . no C5 C6 1.408(5) . . yes C5 C10 1.409(4) . . yes C6 C7 1.350(5) . . yes C6 H6 0.95 . . no C7 C8 1.405(5) . . yes C7 H7 0.95 . . no C8 C9 1.350(5) . . yes C8 H8 0.95 . . no C9 C10 1.415(4) . . yes C9 H9 0.95 . . no C11 C12 1.490(4) . . yes C12 C13 1.384(4) . . yes C12 C17 1.384(4) . . yes C13 C14 1.380(5) . . yes C13 H13 0.95 . . no C14 C15 1.372(5) . . yes C14 H14 0.95 . . no C15 C16 1.373(5) . . yes C15 H15 0.95 . . no C16 C17 1.371(5) . . yes C16 H16 0.95 . . no C17 H17 0.95 . . no C19 C20 1.515(5) . . yes C19 C21 1.508(5) . . yes C19 H19 0.95 . . no C20 H20A 0.95 . . no C20 H20B 0.95 . . no C20 H20C 0.95 . . no C21 H21A 0.95 . . no C21 H21B 0.95 . . no C21 H21C 0.95 . . no C22 C23 1.515(5) . . yes C22 C24 1.512(6) . . yes C22 H22 0.95 . . no C23 H23A 0.95 . . no C23 H23B 0.95 . . no C23 H23C 0.95 . . no C24 H24A 0.95 . . no C24 H24B 0.95 . . no C24 H24C 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 C18 N1 C19 123.5(2) . . . yes C18 N1 C22 119.1(2) . . . yes C19 N1 C22 117.4(2) . . . yes C2 C1 C10 120.4(3) . . . yes C2 C1 C18 122.2(3) . . . yes C10 C1 C18 117.2(2) . . . yes C1 C2 C3 118.8(3) . . . yes C1 C2 C11 120.9(3) . . . yes C3 C2 C11 120.2(3) . . . yes C2 C3 C4 121.4(3) . . . yes C2 C3 H3 119.3 . . . no C4 C3 H3 119.3 . . . no C3 C4 C5 121.2(3) . . . yes C3 C4 H4 119.4 . . . no C5 C4 H4 119.4 . . . no C4 C5 C6 122.0(3) . . . yes C4 C5 C10 118.8(3) . . . yes C6 C5 C10 119.2(3) . . . yes C5 C6 C7 120.6(3) . . . yes C5 C6 H6 119.7 . . . no C7 C6 H6 119.7 . . . no C6 C7 C8 120.8(3) . . . yes C6 C7 H7 119.6 . . . no C8 C7 H7 119.6 . . . no C7 C8 C9 119.7(3) . . . yes C7 C8 H8 120.2 . . . no C9 C8 H8 120.2 . . . no C8 C9 C10 121.4(3) . . . yes C8 C9 H9 119.3 . . . no C10 C9 H9 119.3 . . . no C1 C10 C5 119.4(3) . . . yes C1 C10 C9 122.3(3) . . . yes C5 C10 C9 118.3(3) . . . yes O1 C11 C2 120.1(3) . . . yes O1 C11 C12 118.9(3) . . . yes C2 C11 C12 121.0(3) . . . yes C11 C12 C13 122.9(3) . . . yes C11 C12 C17 118.1(2) . . . yes C13 C12 C17 119.0(3) . . . yes C12 C13 C14 120.4(3) . . . yes C12 C13 H13 119.8 . . . no C14 C13 H13 119.8 . . . no C13 C14 C15 119.7(3) . . . yes C13 C14 H14 120.2 . . . no C15 C14 H14 120.2 . . . no C14 C15 C16 120.5(3) . . . yes C14 C15 H15 119.8 . . . no C16 C15 H15 119.8 . . . no C15 C16 C17 119.9(3) . . . yes C15 C16 H16 120.0 . . . no C17 C16 H16 120.0 . . . no C12 C17 C16 120.6(3) . . . yes C12 C17 H17 119.7 . . . no C16 C17 H17 119.7 . . . no O2 C18 N1 124.3(3) . . . yes O2 C18 C1 117.9(3) . . . yes N1 C18 C1 117.7(2) . . . yes N1 C19 C20 112.5(2) . . . yes N1 C19 C21 112.1(3) . . . yes N1 C19 H19 106.6 . . . no C20 C19 C21 111.9(3) . . . yes C20 C19 H19 106.6 . . . no C21 C19 H19 106.6 . . . no C19 C20 H20A 109.5 . . . no C19 C20 H20B 109.5 . . . no C19 C20 H20C 109.5 . . . no H20A C20 H20B 109.5 . . . no H20A C20 H20C 109.5 . . . no H20B C20 H20C 109.5 . . . no C19 C21 H21A 109.5 . . . no C19 C21 H21B 109.5 . . . no C19 C21 H21C 109.5 . . . no H21A C21 H21B 109.5 . . . no H21A C21 H21C 109.5 . . . no H21B C21 H21C 109.5 . . . no N1 C22 C23 110.8(3) . . . yes N1 C22 C24 112.8(3) . . . yes N1 C22 H22 106.4 . . . no C23 C22 C24 113.5(3) . . . yes C23 C22 H22 106.4 . . . no C24 C22 H22 106.4 . . . no C22 C23 H23A 109.5 . . . no C22 C23 H23B 109.5 . . . no C22 C23 H23C 109.5 . . . no H23A C23 H23B 109.5 . . . no H23A C23 H23C 109.5 . . . no H23B C23 H23C 109.5 . . . no C22 C24 H24A 109.5 . . . no C22 C24 H24B 109.5 . . . no C22 C24 H24C 109.5 . . . no H24A C24 H24B 109.5 . . . no H24A C24 H24C 109.5 . . . no H24B C24 H24C 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 O2 C8 3.138(4) . 3_566 no O2 C14 3.274(4) . 4_464 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C11 C2 C1 . . . . 29.2(4) no O1 C11 C2 C3 . . . . -146.4(3) no O1 C11 C12 C13 . . . . -148.7(3) no O1 C11 C12 C17 . . . . 28.4(5) no O2 C18 N1 C19 . . . . -171.8(3) no O2 C18 N1 C22 . . . . 8.4(4) no O2 C18 C1 C2 . . . . -96.3(3) no O2 C18 C1 C10 . . . . 79.9(3) no N1 C18 C1 C2 . . . . 86.8(3) no N1 C18 C1 C10 . . . . -97.0(3) no C1 C2 C3 C4 . . . . 0.0(4) no C1 C2 C11 C12 . . . . -152.4(3) no C1 C10 C5 C4 . . . . -0.3(4) no C1 C10 C5 C6 . . . . 178.6(2) no C1 C10 C9 C8 . . . . -178.6(3) no C1 C18 N1 C19 . . . . 4.9(4) no C1 C18 N1 C22 . . . . -174.8(3) no C2 C1 C10 C5 . . . . 0.9(4) no C2 C1 C10 C9 . . . . 179.7(3) no C2 C3 C4 C5 . . . . 0.6(4) no C2 C11 C12 C13 . . . . 32.8(5) no C2 C11 C12 C17 . . . . -150.0(3) no C3 C2 C1 C10 . . . . -0.8(4) no C3 C2 C1 C18 . . . . 175.3(2) no C3 C2 C11 C12 . . . . 32.1(4) no C3 C4 C5 C6 . . . . -179.3(3) no C3 C4 C5 C10 . . . . -0.4(4) no C4 C3 C2 C11 . . . . 175.7(3) no C4 C5 C6 C7 . . . . 178.9(3) no C4 C5 C10 C9 . . . . -179.2(3) no C5 C6 C7 C8 . . . . 0.3(5) no C5 C10 C1 C18 . . . . -175.3(2) no C5 C10 C9 C8 . . . . 0.2(4) no C6 C5 C10 C9 . . . . -0.3(4) no C6 C7 C8 C9 . . . . -0.4(5) no C7 C6 C5 C10 . . . . 0.0(4) no C7 C8 C9 C10 . . . . 0.1(5) no C9 C10 C1 C18 . . . . 3.4(4) no C10 C1 C2 C11 . . . . -176.4(2) no C11 C2 C1 C18 . . . . -0.3(4) no C11 C12 C13 C14 . . . . 177.5(3) no C11 C12 C17 C16 . . . . -178.4(3) no C12 C13 C14 C15 . . . . 0.7(5) no C12 C17 C16 C15 . . . . 0.9(5) no C13 C12 C17 C16 . . . . -1.1(5) no C13 C14 C15 C16 . . . . -1.0(6) no C14 C13 C12 C17 . . . . 0.4(5) no C14 C15 C16 C17 . . . . 0.2(6) no C18 N1 C19 C20 . . . . -113.2(3) no C18 N1 C19 C21 . . . . 119.7(3) no C18 N1 C22 C23 . . . . 60.3(4) no C18 N1 C22 C24 . . . . -68.1(4) no C19 N1 C22 C23 . . . . -119.4(3) no C19 N1 C22 C24 . . . . 112.1(3) no C20 C19 N1 C22 . . . . 66.5(4) no C21 C19 N1 C22 . . . . -60.6(4) no #------------------------------------------------------------------------------ data_S587 #------------------------------------------------------------------------------ _audit_creation_date '1997-04-11' _audit_creation_method 'by teXsan v1.7' _audit_update_record ; ? ; #------------------------------------------------------------------------------ _publ_requested_journal ' ENTER JOURNAL NAME HERE' _publ_contact_author ; ENTER NAME ENTER ADDRESS ; _publ_contact_letter ; ENTER TEXT OF LETTER ; _publ_requested_coeditor_name ? _publ_contact_author_phone ' ENTER PHONE NUMBER ' _publ_contact_author_fax ' ENTER FAX NUMBER ' _publ_contact_author_email ' ENTER EMAIL ADDRESS ' loop_ _publ_author_name _publ_author_address ' FIRST AUTHORS NAME ' ; FIRST AUTHORS ADDRESS ; _publ_section_title ; ENTER SECTION TITLE ; _publ_section_abstract ; ENTER ABSTRACT ; _publ_section_exptl_prep ; ENTER EXPERIMENTAL SECTION ; _publ_section_exptl_refinement ; ENTER EXPERIMENTAL SECTION ; _publ_section_comment ; ENTER TEXT ; _publ_section_references ; ENTER OTHER REFERENCES Molecular Structure Corporation. (1995). teXsan. Single Crystal Structure Analysis Software. Version 1.7. 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. Zachariasen, W. H. (1967). Acta Cryst. 23, 558-564. ; _publ_section_acknowledgements ; ENTER ACKNOWLEDGEMENTS ; _publ_section_table_legends ; ENTER TABLE LEGENDS ; _publ_section_figure_captions ; ENTER FIGURE CAPTIONS ; #------------------------------------------------------------------------------ _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan (MSC, 1995)' _computing_structure_solution ? _computing_structure_refinement 'teXsan (MSC, 1995)' _computing_publication_material 'teXsan (MSC, 1995)' #------------------------------------------------------------------------------ _cell_length_a 12.404(1) _cell_length_b 19.6149(8) _cell_length_c 16.222(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 3947.1(5) _cell_formula_units_Z 8 _cell_measurement_temperature 293.2 _cell_measurement_reflns_used 21 _cell_measurement_theta_min 38.9 _cell_measurement_theta_max 39.9 #------------------------------------------------------------------------------ _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c a ' _symmetry_Int_Tables_number 61 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' '1/2+x,1/2-y, -z' ' -x,1/2+y,1/2-z' '1/2-x, -y,1/2+z' ' -x, -y, -z' '1/2-x,1/2+y, +z' ' +x,1/2-y,1/2+z' '1/2+x, +y,1/2-z' #------------------------------------------------------------------------------ _exptl_crystal_description 'block' _exptl_crystal_colour 'colourlessblock' _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.40 _exptl_crystal_density_diffrn 1.102 _exptl_crystal_density_meas 'not measured' _chemical_formula_weight 327.47 _chemical_formula_analytical ? _chemical_formula_sum 'C21 H29 N O2 ' _chemical_formula_moiety 'C21 H29 N O2 ' _chemical_formula_structural ? _chemical_compound_source ? _exptl_crystal_F_000 1424.00 _exptl_absorpt_coefficient_mu 0.546 _exptl_absorpt_correction_type ; \y scans (North,Phillips & Matthews, 1968) ; _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.781 _exptl_special_details ; The scan width was (1.73+0.30tan\q)\% with an \w scan speed of 16\% per minute (up to 4 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. ; #------------------------------------------------------------------------------ _diffrn_special_details ; ? ; _diffrn_ambient_temperature 293.2 _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device 'Rigaku AFC5R' _diffrn_measurement_method \w-2\q _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% 2.66 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -1 -4 4 -1 -5 -1 -1 -5 1 _diffrn_reflns_number 4527 _reflns_number_total 4527 _reflns_number_observed 2892 _reflns_observed_criterion >2.00\s(I) _diffrn_reflns_av_R_equivalents 0.00000 _diffrn_reflns_av_sigmaI/netI 0.060 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.72 _diffrn_reflns_theta_max 79.16 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 -0.00634 _diffrn_orient_matrix_UB_12 0.04910 _diffrn_orient_matrix_UB_13 -0.01586 _diffrn_orient_matrix_UB_21 -0.00219 _diffrn_orient_matrix_UB_22 -0.01326 _diffrn_orient_matrix_UB_23 -0.05950 _diffrn_orient_matrix_UB_31 -0.08034 _diffrn_orient_matrix_UB_32 -0.00352 _diffrn_orient_matrix_UB_33 0.00287 #------------------------------------------------------------------------------ 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 0 168 0.018 0.009 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; H 0 232 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; N 0 8 0.031 0.018 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; O 0 16 0.049 0.032 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ 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_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom O(1) 0.1857(1) 0.36126(7) 0.65131(8) 0.0646(5) 1.000 . Uani d ? O(2) 0.3741(1) 0.44256(7) 0.6170(1) 0.0893(6) 1.000 . Uani d ? N(1) 0.2362(1) 0.33308(8) 0.52148(10) 0.0539(5) 1.000 . Uani d ? C(1) 0.3471(2) 0.29825(9) 0.6400(1) 0.0473(6) 1.000 . Uani d ? C(2) 0.4357(2) 0.33141(10) 0.6698(1) 0.0551(6) 1.000 . Uani d ? C(3) 0.5170(2) 0.2932(1) 0.7104(1) 0.0645(7) 1.000 . Uani d ? C(4) 0.5097(2) 0.2246(1) 0.7188(1) 0.0661(7) 1.000 . Uani d ? C(5) 0.4206(2) 0.1891(1) 0.6889(1) 0.0579(7) 1.000 . Uani d ? C(6) 0.4109(2) 0.1170(1) 0.6967(1) 0.0803(9) 1.000 . Uani d ? C(7) 0.3244(3) 0.0837(1) 0.6685(2) 0.097(1) 1.000 . Uani d ? C(8) 0.2394(2) 0.1195(1) 0.6320(2) 0.0895(10) 1.000 . Uani d ? C(9) 0.2453(2) 0.1888(1) 0.6231(1) 0.0685(7) 1.000 . Uani d ? C(10) 0.3366(2) 0.22574(10) 0.6502(1) 0.0511(6) 1.000 . Uani d ? C(11) 0.2507(2) 0.33456(10) 0.6033(1) 0.0494(6) 1.000 . Uani d ? C(12) 0.3212(2) 0.3102(1) 0.4640(1) 0.0666(7) 1.000 . Uani d ? C(13) 0.2838(2) 0.2537(1) 0.4078(2) 0.099(1) 1.000 . Uani d ? C(14) 0.3674(2) 0.3706(2) 0.4155(2) 0.111(1) 1.000 . Uani d ? C(15) 0.1369(2) 0.3635(1) 0.4855(1) 0.0709(8) 1.000 . Uani d ? C(16) 0.0377(2) 0.3243(2) 0.5112(2) 0.0981(10) 1.000 . Uani d ? C(17) 0.1283(2) 0.4393(1) 0.5010(2) 0.104(1) 1.000 . Uani d ? C(18) 0.4564(2) 0.4086(1) 0.6625(2) 0.0855(9) 1.000 . Uani d ? C(19) 0.5582(2) 0.4203(2) 0.6114(3) 0.154(2) 1.000 . Uani d ? C(20) 0.4652(3) 0.4397(1) 0.7499(3) 0.141(2) 1.000 . Uani d ? C(21) 0.3662(4) 0.4332(2) 0.8006(2) 0.164(2) 1.000 . Uani d ? H(2) 0.3188 0.4398 0.6419 0.090 1.000 . Uiso c ? H(3) 0.5770 0.3160 0.7321 0.067 1.000 . Uiso c ? H(4) 0.5667 0.2009 0.7455 0.065 1.000 . Uiso c ? H(6) 0.4726 0.0956 0.7213 0.099 1.000 . Uiso c ? H(7) 0.3225 0.0321 0.6746 0.115 1.000 . Uiso c ? H(8) 0.1757 0.0968 0.6141 0.108 1.000 . Uiso c ? H(9) 0.1865 0.2118 0.5975 0.063 1.000 . Uiso c ? H(12) 0.3790 0.2946 0.5024 0.058 1.000 . Uiso c ? H(13a) 0.2269 0.2686 0.3720 0.126 1.000 . Uiso c ? H(13b) 0.2539 0.2122 0.4371 0.146 1.000 . Uiso c ? H(13c) 0.3427 0.2392 0.3726 0.119 1.000 . Uiso c ? H(14b) 0.3068 0.3832 0.3759 0.156 1.000 . Uiso c ? H(14a) 0.4330 0.3554 0.3828 0.128 1.000 . Uiso c ? H(14c) 0.3952 0.3997 0.4583 0.154 1.000 . Uiso c ? H(15) 0.1472 0.3584 0.4242 0.057 1.000 . Uiso c ? H(16c) 0.0340 0.2772 0.4913 0.177 1.000 . Uiso c ? H(16a) -0.0243 0.3448 0.4850 0.106 1.000 . Uiso c ? H(16b) 0.0257 0.3259 0.5712 0.097 1.000 . Uiso c ? H(17a) 0.0739 0.4554 0.4655 0.127 1.000 . Uiso c ? H(17c) 0.1947 0.4631 0.4915 0.119 1.000 . Uiso c ? H(17b) 0.1125 0.4460 0.5610 0.144 1.000 . Uiso c ? H(19b) 0.5688 0.4680 0.6034 0.185 1.000 . Uiso c ? H(19a) 0.6191 0.4021 0.6399 0.185 1.000 . Uiso c ? H(19c) 0.5515 0.3985 0.5595 0.185 1.000 . Uiso c ? H(20a) 0.5301 0.4222 0.7796 0.165 1.000 . Uiso c ? H(20b) 0.4817 0.4829 0.7346 0.151 1.000 . Uiso c ? H(21c) 0.3062 0.4574 0.7794 0.182 1.000 . Uiso c ? H(21b) 0.3551 0.3810 0.8143 0.321 1.000 . Uiso c ? H(21a) 0.3705 0.4441 0.8545 0.189 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) 0.0563(9) 0.080(1) 0.0577(9) 0.0108(8) 0.0049(8) -0.0063(8) O(2) 0.084(1) 0.0522(9) 0.131(1) -0.0016(9) -0.019(1) 0.0150(9) N(1) 0.0495(10) 0.064(1) 0.0478(9) 0.0058(9) 0.0010(9) 0.0012(8) C(1) 0.050(1) 0.047(1) 0.045(1) 0.0008(9) 0.0013(10) -0.0006(9) C(2) 0.053(1) 0.047(1) 0.065(1) 0.0005(10) -0.007(1) -0.004(1) C(3) 0.056(1) 0.066(1) 0.071(1) 0.004(1) -0.015(1) -0.009(1) C(4) 0.075(2) 0.064(1) 0.059(1) 0.021(1) -0.011(1) 0.002(1) C(5) 0.077(2) 0.049(1) 0.047(1) 0.009(1) 0.003(1) 0.0005(10) C(6) 0.115(2) 0.051(1) 0.074(2) 0.014(1) 0.005(2) 0.006(1) C(7) 0.140(3) 0.047(1) 0.104(2) -0.008(2) 0.012(2) 0.004(1) C(8) 0.107(2) 0.061(2) 0.101(2) -0.028(2) 0.007(2) -0.005(1) C(9) 0.072(2) 0.059(1) 0.075(2) -0.012(1) 0.000(1) 0.000(1) C(10) 0.062(1) 0.048(1) 0.044(1) -0.003(1) 0.007(1) -0.0024(9) C(11) 0.047(1) 0.048(1) 0.053(1) -0.0038(10) 0.003(1) -0.0004(10) C(12) 0.060(1) 0.088(2) 0.052(1) 0.009(1) 0.004(1) -0.001(1) C(13) 0.100(2) 0.124(2) 0.075(2) 0.016(2) 0.000(2) -0.034(2) C(14) 0.106(2) 0.145(3) 0.083(2) -0.011(2) 0.034(2) 0.018(2) C(15) 0.064(2) 0.093(2) 0.056(1) 0.019(1) -0.009(1) 0.002(1) C(16) 0.052(2) 0.156(3) 0.087(2) -0.002(2) -0.014(1) -0.009(2) C(17) 0.112(2) 0.100(2) 0.101(2) 0.042(2) -0.016(2) 0.016(2) C(18) 0.068(2) 0.050(1) 0.139(3) -0.007(1) -0.031(2) 0.004(2) C(19) 0.076(2) 0.094(2) 0.293(5) -0.027(2) 0.004(3) 0.058(3) C(20) 0.155(3) 0.059(2) 0.208(4) 0.011(2) -0.107(3) -0.043(2) C(21) 0.221(4) 0.154(4) 0.117(3) 0.083(4) -0.057(3) -0.064(3) #------------------------------------------------------------------------------ _refine_special_details ; ? ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme 'w = 1/[\s^2^(Fo) + 0.00002|Fo|^2^]' _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method 'Zachariasen (1967)' _refine_ls_extinction_coef 0.00000023(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 2892 _refine_ls_number_parameters 218 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.0844 _refine_ls_R_factor_obs 0.0569 _refine_ls_wR_factor_all 0.0468 _refine_ls_wR_factor_obs 0.0454 _refine_ls_goodness_of_fit_all 2.669 _refine_ls_goodness_of_fit_obs 3.098 _refine_ls_shift/esd_max 0.0003 _refine_ls_shift/esd_mean 0.0237 _refine_diff_density_min -0.20 _refine_diff_density_max 0.24 #------------------------------------------------------------------------------ _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(11) 1.237(2) . . yes O(2) C(18) 1.425(3) . . yes O(2) H(2) 0.80 . . no N(1) C(11) 1.340(2) . . yes N(1) C(12) 1.477(2) . . yes N(1) C(15) 1.488(2) . . yes C(1) C(2) 1.366(2) . . yes C(1) C(10) 1.438(2) . . yes C(1) C(11) 1.514(3) . . yes C(2) C(3) 1.418(3) . . yes C(2) C(18) 1.540(3) . . yes C(3) C(4) 1.355(3) . . yes C(3) H(3) 0.94 . . no C(4) C(5) 1.393(3) . . yes C(4) H(4) 0.95 . . no C(5) C(6) 1.425(3) . . yes C(5) C(10) 1.413(3) . . yes C(6) C(7) 1.337(3) . . yes C(6) H(6) 0.96 . . no C(7) C(8) 1.398(4) . . yes C(7) H(7) 1.02 . . no C(8) C(9) 1.369(3) . . yes C(8) H(8) 0.95 . . no C(9) C(10) 1.414(3) . . yes C(9) H(9) 0.95 . . no C(12) C(13) 1.509(3) . . yes C(12) C(14) 1.533(3) . . yes C(12) H(12) 1.00 . . no C(13) H(13a) 0.96 . . no C(13) H(13b) 1.01 . . no C(13) H(13c) 0.97 . . no C(14) H(14b) 1.02 . . no C(14) H(14a) 1.02 . . no C(14) H(14c) 0.96 . . no C(15) C(16) 1.509(3) . . yes C(15) C(17) 1.512(3) . . yes C(15) H(15) 1.01 . . no C(16) H(16c) 0.98 . . no C(16) H(16a) 0.97 . . no C(16) H(16b) 0.99 . . no C(17) H(17a) 0.94 . . no C(17) H(17c) 0.96 . . no C(17) H(17b) 1.00 . . no C(18) C(19) 1.528(4) . . yes C(18) C(20) 1.548(4) . . yes C(19) H(19b) 0.95 . . no C(19) H(19a) 0.95 . . no C(19) H(19c) 0.95 . . no C(20) C(21) 1.484(5) . . yes C(20) H(20a) 1.00 . . no C(20) H(20b) 0.91 . . no C(21) H(21c) 0.95 . . no C(21) H(21b) 1.06 . . no C(21) H(21a) 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(18) O(2) H(2) 108.8 . . . no C(11) N(1) C(12) 122.5(2) . . . yes C(11) N(1) C(15) 119.3(2) . . . yes C(12) N(1) C(15) 117.7(2) . . . yes C(2) C(1) C(10) 120.2(2) . . . yes C(2) C(1) C(11) 123.4(2) . . . yes C(10) C(1) C(11) 116.1(2) . . . yes C(1) C(2) C(3) 119.0(2) . . . yes C(1) C(2) C(18) 125.1(2) . . . yes C(3) C(2) C(18) 115.9(2) . . . yes C(2) C(3) C(4) 121.6(2) . . . yes C(2) C(3) H(3) 119.1 . . . no C(4) C(3) H(3) 119.3 . . . no C(3) C(4) C(5) 120.9(2) . . . yes C(3) C(4) H(4) 118.9 . . . no C(5) C(4) H(4) 120.2 . . . no C(4) C(5) C(6) 122.2(2) . . . yes C(4) C(5) C(10) 119.0(2) . . . yes C(6) C(5) C(10) 118.8(2) . . . yes C(5) C(6) C(7) 121.5(2) . . . yes C(5) C(6) H(6) 113.9 . . . no C(7) C(6) H(6) 124.6 . . . no C(6) C(7) C(8) 120.3(2) . . . yes C(6) C(7) H(7) 118.1 . . . no C(8) C(7) H(7) 121.5 . . . no C(7) C(8) C(9) 120.2(2) . . . yes C(7) C(8) H(8) 121.4 . . . no C(9) C(8) H(8) 118.5 . . . no C(8) C(9) C(10) 121.3(2) . . . yes C(8) C(9) H(9) 118.4 . . . no C(10) C(9) H(9) 120.4 . . . no C(1) C(10) C(5) 119.2(2) . . . yes C(1) C(10) C(9) 122.9(2) . . . yes C(5) C(10) C(9) 117.9(2) . . . yes O(1) C(11) N(1) 123.1(2) . . . yes O(1) C(11) C(1) 117.8(2) . . . yes N(1) C(11) C(1) 119.0(2) . . . yes N(1) C(12) C(13) 112.7(2) . . . yes N(1) C(12) C(14) 110.8(2) . . . yes N(1) C(12) H(12) 102.2 . . . no C(13) C(12) C(14) 111.9(2) . . . yes C(13) C(12) H(12) 111.9 . . . no C(14) C(12) H(12) 106.8 . . . no C(12) C(13) H(13a) 111.5 . . . no C(12) C(13) H(13b) 114.7 . . . no C(12) C(13) H(13c) 109.8 . . . no H(13a) C(13) H(13b) 105.1 . . . no H(13a) C(13) H(13c) 106.8 . . . no H(13b) C(13) H(13c) 108.5 . . . no C(12) C(14) H(14b) 103.6 . . . no C(12) C(14) H(14a) 109.9 . . . no C(12) C(14) H(14c) 102.9 . . . no H(14b) C(14) H(14a) 109.4 . . . no H(14b) C(14) H(14c) 125.0 . . . no H(14a) C(14) H(14c) 105.3 . . . no N(1) C(15) C(16) 111.3(2) . . . yes N(1) C(15) C(17) 112.8(2) . . . yes N(1) C(15) H(15) 104.1 . . . no C(16) C(15) C(17) 113.4(2) . . . yes C(16) C(15) H(15) 109.0 . . . no C(17) C(15) H(15) 105.6 . . . no C(15) C(16) H(16c) 115.3 . . . no C(15) C(16) H(16a) 108.4 . . . no C(15) C(16) H(16b) 112.4 . . . no H(16c) C(16) H(16a) 102.1 . . . no H(16c) C(16) H(16b) 110.3 . . . no H(16a) C(16) H(16b) 107.6 . . . no C(15) C(17) H(17a) 106.2 . . . no C(15) C(17) H(17c) 113.0 . . . no C(15) C(17) H(17b) 107.7 . . . no H(17a) C(17) H(17c) 110.8 . . . no H(17a) C(17) H(17b) 114.2 . . . no H(17c) C(17) H(17b) 105.1 . . . no O(2) C(18) C(2) 112.3(2) . . . yes O(2) C(18) C(19) 104.0(2) . . . yes O(2) C(18) C(20) 109.9(2) . . . yes C(2) C(18) C(19) 109.1(2) . . . yes C(2) C(18) C(20) 109.2(2) . . . yes C(19) C(18) C(20) 112.3(3) . . . yes C(18) C(19) H(19b) 109.6 . . . no C(18) C(19) H(19a) 109.5 . . . no C(18) C(19) H(19c) 109.9 . . . no H(19b) C(19) H(19a) 108.9 . . . no H(19b) C(19) H(19c) 109.5 . . . no H(19a) C(19) H(19c) 109.4 . . . no C(18) C(20) C(21) 114.6(3) . . . yes C(18) C(20) H(20a) 111.3 . . . no C(18) C(20) H(20b) 97.7 . . . no C(21) C(20) H(20a) 111.7 . . . no C(21) C(20) H(20b) 114.7 . . . no H(20a) C(20) H(20b) 105.7 . . . no C(20) C(21) H(21c) 113.9 . . . no C(20) C(21) H(21b) 108.0 . . . no C(20) C(21) H(21a) 117.9 . . . no H(21c) C(21) H(21b) 117.4 . . . no H(21c) C(21) H(21a) 106.3 . . . no H(21b) C(21) H(21a) 91.9 . . . 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(3) 3.346(3) . 8_456 no O(1) C(20) 3.523(3) . 8_456 no C(5) C(16) 3.567(3) . 2_556 no C(6) C(14) 3.598(4) . 7 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O(1) C(11) N(1) C(12) . . . . 170.9(2) no O(1) C(11) N(1) C(15) . . . . -1.3(3) no O(1) C(11) C(1) C(2) . . . . -77.7(3) no O(1) C(11) C(1) C(10) . . . . 95.9(2) no O(2) C(18) C(2) C(1) . . . . -2.8(3) no O(2) C(18) C(2) C(3) . . . . 176.8(2) no O(2) C(18) C(20) C(21) . . . . 61.5(4) no N(1) C(11) C(1) C(2) . . . . 106.0(2) no N(1) C(11) C(1) C(10) . . . . -80.4(2) no C(1) C(2) C(3) C(4) . . . . 1.4(3) no C(1) C(2) C(18) C(19) . . . . -117.5(3) no C(1) C(2) C(18) C(20) . . . . 119.4(3) no C(1) C(10) C(5) C(4) . . . . 2.3(3) no C(1) C(10) C(5) C(6) . . . . -178.2(2) no C(1) C(10) C(9) C(8) . . . . 178.3(2) no C(1) C(11) N(1) C(12) . . . . -13.1(3) no C(1) C(11) N(1) C(15) . . . . 174.8(2) no C(2) C(1) C(10) C(5) . . . . -2.1(3) no C(2) C(1) C(10) C(9) . . . . 178.0(2) no C(2) C(3) C(4) C(5) . . . . -1.2(4) no C(2) C(18) C(20) C(21) . . . . -62.1(3) no C(3) C(2) C(1) C(10) . . . . 0.3(3) no C(3) C(2) C(1) C(11) . . . . 173.7(2) no C(3) C(2) C(18) C(19) . . . . 62.0(3) no C(3) C(2) C(18) C(20) . . . . -61.0(3) no C(3) C(4) C(5) C(6) . . . . 179.8(2) no C(3) C(4) C(5) C(10) . . . . -0.7(3) no C(4) C(3) C(2) C(18) . . . . -178.2(2) no C(4) C(5) C(6) C(7) . . . . 179.3(2) no C(4) C(5) C(10) C(9) . . . . -177.8(2) no C(5) C(6) C(7) C(8) . . . . -1.5(4) no C(5) C(10) C(1) C(11) . . . . -176.0(2) no C(5) C(10) C(9) C(8) . . . . -1.6(3) no C(6) C(5) C(10) C(9) . . . . 1.7(3) no C(6) C(7) C(8) C(9) . . . . 1.6(4) no C(7) C(6) C(5) C(10) . . . . -0.1(4) no C(7) C(8) C(9) C(10) . . . . 0.0(4) no C(9) C(10) C(1) C(11) . . . . 4.2(3) no C(10) C(1) C(2) C(18) . . . . 179.8(2) no C(11) N(1) C(12) C(13) . . . . 125.2(2) no C(11) N(1) C(12) C(14) . . . . -108.5(2) no C(11) N(1) C(15) C(16) . . . . -65.9(3) no C(11) N(1) C(15) C(17) . . . . 62.9(3) no C(11) C(1) C(2) C(18) . . . . -6.8(3) no C(12) N(1) C(15) C(16) . . . . 121.6(2) no C(12) N(1) C(15) C(17) . . . . -109.6(2) no C(13) C(12) N(1) C(15) . . . . -62.5(3) no C(14) C(12) N(1) C(15) . . . . 63.7(3) no C(19) C(18) C(20) C(21) . . . . 176.7(3) no #------------------------------------------------------------------------------