# Supplementary Material (ESI) for ChemComm # This journal is © The Royal Society of Chemistry 1999 # CCDC Number: 182/1432 #=============================================================================== data_global #=============================================================================== _audit_creation_date 20-04-99 # 1. SUBMISSION DETAILS _publ_contact_author_name # Name of author for correspondance ; Norbert Hoffmann ; _publ_contact_author_address # Address of author for correspondance ; Universite de Reims, CNRS UMR 6519 B.P. 1039 F-51687 Reims, cedex 2 France; ; _publ_contact_author_phone '+ 33 3 26 91 31 96' _publ_contact_author_fax '+ 33 3 26 91 31 66' _publ_contact_author_email norbert.hoffmann@univ-reims.fr _publ_requested_journal Chem.Commun. _publ_contact_letter ; ; _publ_requested_category FM #=============================================================================== # 2. PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ; ? ; _journal_techeditor_code ? _journal_techeditor_notes ; ? ; _journal_coden_ASTM ? _journal_name_full ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #=============================================================================== # 3. TITLE AND AUTHOR LIST _publ_section_title ; ? ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address 'Dupont Karl' #<--'Last name, first name' ; Research School of Chemistry National Laboratory Ouchnock Islandia ; # 4. TEXT _publ_section_abstract ; ? ; _publ_section_comment ; ? ; _publ_section_exptl_prep ; ? ; _publ_section_exptl_refinement ; ? ; _publ_section_references ; Burla, M.C., Camalli, M., Cascarano, G.,Giacovazzo, C., Polidori, G., Spagna, R. &Viterbo, D. (1989). SIR. J. Appl. Cryst. 22, 389-393. OpenMoleN, Interactive Intelligent Structure solution (1997) Nonius B.V., Delft, The Netherlands. North, A.C.T., Phillips, D.C., Mathews, F.S. (1968). Acta Cryst., A24, 351-359. ; _publ_section_figure_captions ; ? ; _publ_section_acknowledgements ; ? ; #=============================================================================== # If more than one structure is reported, sections 5-10 should be filled in # per structure. For each data set, replace the ? in the data_? line below # by a unique identifier. data_st985 #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C22 H31 N O3' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C22 H31 N O3' _chemical_formula_weight 357.50 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C ? 0.002 0.002 International_Tables_Vol_IV_Table_2.3.1 H ? 0.000 0.000 International_Tables_Vol_IV_Table_2.3.1 N ? 0.004 0.003 International_Tables_Vol_IV_Table_2.3.1 O ? 0.008 0.006 International_Tables_Vol_IV_Table_2.3.1 #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall ' P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x,y,z' 1/2-x,-y,1/2+z -x,1/2+y,1/2-z 1/2+x,1/2-y,-z _cell_length_a 8.4839(3) _cell_length_b 13.709(1) _cell_length_c 17.887(1) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2080.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 294 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 18.1 _cell_measurement_theta_max 21.1 _cell_special_details ; ? ; _exptl_crystal_description prism _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.14 _exptl_crystal_density_method 'none' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type psi_scan_(North,_Phillips,_Mathews,_1968) _exptl_absorpt_correction_T_min 0.9204 _exptl_absorpt_correction_T_max 1.0000 #=============================================================================== # 7. EXPERIMENTAL DATA _diffrn_special_details ; ? ; _diffrn_ambient_temperature 294 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type Mo-K\a _diffrn_source xray_tube _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type Enraf_Nonius_CAD4 _diffrn_measurement_method \q/2\q _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 0 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 3 -3 6 -3 -1 7 3 11 0 _diffrn_reflns_number 2428 _diffrn_reflns_av_R_equivalents 0 _diffrn_reflns_av_sigmaI/netI 0.333 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 2.5 _diffrn_reflns_theta_max 26.29 _reflns_number_total 2428 _reflns_number_gt 1459 _reflns_threshold_expression >3.0\s(I) _computing_data_collection 'CAD4_(Enraf-Nonius,_1994)' _computing_cell_refinement CAD4_(Enraf-Nonius,_1994) _computing_data_reduction 'process_OpenMoleN_(_1997)' _computing_structure_solution Direct_methods_(SIR,_Burla_et_al.,_1989) _computing_structure_refinement LSFM_OpenMoleN_(_1997) _computing_molecular_graphics ? _computing_publication_material CIFGEN_IN_OpenMoleN_(_1997) #=============================================================================== # 8. REFINEMENT DATA _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme '4Fo^2^/(\s^2^(Fo^2^) + 0.0064 Fo^4^)' _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_expression ? _refine_ls_extinction_coef ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1459 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_R_factor_all 0.102 _refine_ls_R_factor_gt 0.039 _refine_ls_wR_factor_all 0.070 _refine_ls_wR_factor_ref 0.051 _refine_ls_goodness_of_fit_all 1.416 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_shift/su_max 0.004 _refine_ls_shift/esd_mean 0.001 _refine_diff_density_max 0.151 _refine_diff_density_min -0.199 #=============================================================================== # 9. 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_adp_type _atom_site_calc_flag _atom_site_calc_attached_atom _atom_site_type_symbol C1 -0.2602(4) 0.5430(2) 0.4861(2) 0.055(2) Uani ? ? C C2 -0.2561(4) 0.6430(2) 0.4795(2) 0.066(2) Uani ? ? C C3 -0.1154(5) 0.6866(2) 0.4639(2) 0.064(2) Uani ? ? C C4 0.0198(4) 0.6330(2) 0.4565(2) 0.057(2) Uani ? ? C C5 0.0175(3) 0.5316(2) 0.4634(1) 0.041(1) Uani ? ? C C6 -0.1273(3) 0.4865(2) 0.4773(1) 0.039(1) Uani ? ? C C7 -0.1429(3) 0.3758(2) 0.4797(1) 0.041(1) Uani ? ? C C8 0.0131(4) 0.3225(2) 0.4731(2) 0.041(1) Uani ? ? C C9 0.1534(4) 0.3835(2) 0.4954(2) 0.055(2) Uani ? ? C N 0.1533(3) 0.4747(2) 0.4547(1) 0.049(1) Uani ? ? N C10 0.3057(4) 0.5225(3) 0.4501(3) 0.078(2) Uani ? ? C C11 0.0197(3) 0.2928(2) 0.3914(2) 0.043(1) Uani ? ? C O1 -0.1426(2) 0.2900(1) 0.3656(1) 0.052(1) Uani ? ? O C12 -0.2364(4) 0.3392(2) 0.4140(2) 0.043(1) Uani ? ? C O2 -0.3744(2) 0.3492(2) 0.4013(1) 0.057(1) Uani ? ? O O3 0.0882(2) 0.2025(1) 0.3835(1) 0.047(1) Uani ? ? O C13 0.1485(4) 0.1802(2) 0.3093(2) 0.049(2) Uani ? ? C C14 0.3046(4) 0.2309(3) 0.2964(2) 0.062(2) Uani ? ? C C15 0.3762(4) 0.2050(3) 0.2209(2) 0.071(2) Uani ? ? C C16 0.5315(5) 0.2598(5) 0.2081(3) 0.114(3) Uani ? ? C C17 0.3929(5) 0.0957(3) 0.2162(2) 0.080(2) Uani ? ? C C18 0.2381(5) 0.0434(3) 0.2285(2) 0.072(2) Uani ? ? C C19 0.1623(4) 0.0700(2) 0.3042(2) 0.054(2) Uani ? ? C C20 0.0070(5) 0.0166(3) 0.3192(2) 0.069(2) Uani ? ? C C21 0.0291(6) -0.0937(3) 0.3243(2) 0.093(3) Uani ? ? C C22 -0.1212(5) 0.0402(3) 0.2640(3) 0.096(3) Uani ? ? C H1 -0.3577 0.5120 0.4972 0.0732 Uiso calc C1 H H2 -0.3491 0.6808 0.4855 0.0884 Uiso calc C2 H H3 -0.1112 0.7555 0.4582 0.0897 Uiso calc C3 H H4 0.1166 0.6653 0.4464 0.0763 Uiso calc C4 H H5 -0.1912 0.3633 0.5267 0.0534 Uiso calc C7 H H6 0.0184 0.2687 0.5065 0.0540 Uiso calc C8 H H7 0.2474 0.3487 0.4845 0.0723 Uiso calc C9 H H8 0.1486 0.3966 0.5475 0.0723 Uiso calc C9 H H9 0.3859 0.4748 0.4442 0.1182 Uiso calc C10 H H10 0.3068 0.5654 0.4084 0.1182 Uiso calc C10 H H11 0.3240 0.5586 0.4945 0.1182 Uiso calc C10 H H12 0.0813 0.3375 0.3632 0.0561 Uiso calc C11 H H13 0.0797 0.2033 0.2713 0.0635 Uiso calc C13 H H14 0.3759 0.2120 0.3347 0.0814 Uiso calc C14 H H15 0.2886 0.2994 0.2984 0.0814 Uiso calc C14 H H16 0.3086 0.2253 0.1815 0.0960 Uiso calc C15 H H17 0.5133 0.3281 0.2117 0.1537 Uiso calc C16 H H18 0.6061 0.2406 0.2448 0.1537 Uiso calc C16 H H19 0.5711 0.2448 0.1598 0.1537 Uiso calc C16 H H20 0.4658 0.0749 0.2532 0.1064 Uiso calc C17 H H21 0.4320 0.0791 0.1681 0.1064 Uiso calc C17 H H22 0.2564 -0.0250 0.2273 0.0933 Uiso calc C18 H H23 0.1674 0.0607 0.1895 0.0933 Uiso calc C18 H H24 0.2291 0.0477 0.3432 0.0713 Uiso calc C19 H H25 -0.0267 0.0404 0.3664 0.0911 Uiso calc C20 H H26 -0.0698 -0.1239 0.3336 0.1303 Uiso calc C21 H H27 0.0712 -0.1175 0.2786 0.1303 Uiso calc C21 H H28 0.0997 -0.1085 0.3640 0.1303 Uiso calc C21 H H29 -0.2138 0.0048 0.2765 0.1276 Uiso calc C22 H H30 -0.1430 0.1082 0.2654 0.1276 Uiso calc C22 H H31 -0.0878 0.0226 0.2151 0.1276 Uiso calc C22 H 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 _atom_site_aniso_type_symbol C1 0.041(2) 0.060(2) 0.068(2) 0.010(2) 0.006(2) -0.016(2) C C2 0.061(2) 0.050(2) 0.093(2) 0.021(2) -0.006(2) -0.022(2) C C3 0.079(2) 0.036(1) 0.092(2) 0.007(2) -0.011(2) -0.012(2) C C4 0.056(2) 0.044(2) 0.076(2) -0.008(2) -0.002(2) -0.009(2) C C5 0.038(1) 0.039(1) 0.048(1) -0.000(1) -0.002(1) -0.006(1) C C6 0.038(1) 0.040(1) 0.039(1) 0.002(1) 0.001(1) -0.008(1) C C7 0.043(1) 0.043(1) 0.037(1) -0.003(1) 0.007(1) 0.002(1) C C8 0.046(2) 0.035(1) 0.044(1) 0.007(1) -0.005(1) -0.000(1) C C9 0.045(2) 0.052(2) 0.070(2) 0.012(2) -0.013(2) -0.012(2) C N 0.030(1) 0.046(1) 0.082(2) -0.004(1) 0.003(1) -0.012(1) N C10 0.039(2) 0.075(2) 0.158(4) -0.008(2) 0.009(2) -0.022(3) C C11 0.049(2) 0.038(1) 0.043(1) -0.002(1) 0.001(1) -0.001(1) C O1 0.052(1) 0.055(1) 0.048(1) 0.005(1) -0.009(1) -0.0090(9) O C12 0.042(1) 0.035(1) 0.053(2) -0.007(1) 0.002(1) 0.002(1) C O2 0.039(1) 0.066(1) 0.072(1) -0.007(1) -0.004(1) -0.001(1) O O3 0.059(1) 0.0409(9) 0.0428(9) 0.011(1) 0.0011(9) -0.0048(9) O C13 0.050(2) 0.054(2) 0.043(1) 0.007(2) -0.001(1) -0.006(1) C C14 0.058(2) 0.068(2) 0.062(2) -0.001(2) 0.004(2) -0.008(2) C C15 0.054(2) 0.106(2) 0.061(2) -0.005(2) 0.011(2) -0.013(2) C C16 0.083(3) 0.163(4) 0.109(3) -0.032(3) 0.034(3) -0.024(3) C C17 0.067(2) 0.107(3) 0.072(2) 0.017(2) 0.007(2) -0.029(2) C C18 0.079(2) 0.068(2) 0.068(2) 0.015(2) 0.002(2) -0.020(2) C C19 0.062(2) 0.057(2) 0.046(2) 0.016(2) -0.008(2) -0.011(1) C C20 0.086(2) 0.057(2) 0.067(2) -0.005(2) 0.005(2) -0.012(2) C C21 0.154(4) 0.062(2) 0.084(3) -0.014(3) -0.009(3) -0.011(2) C C22 0.074(2) 0.094(3) 0.126(3) -0.015(3) -0.008(3) -0.010(3) C # 10. MOLECULAR GEOMETRY 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 C1 C2 1.377(5) . . ? C1 C6 1.377(5) . . ? C2 C3 1.363(6) . . ? C3 C4 1.369(6) . . ? C4 C5 1.396(5) . . ? C5 C6 1.398(4) . . ? C5 N 1.400(4) . . ? C6 C7 1.524(4) . . ? C7 C8 1.517(5) . . ? C7 C12 1.504(4) . . ? C8 C9 1.508(5) . . ? C8 C11 1.519(4) . . ? C9 N 1.447(5) . . ? N C10 1.452(5) . . ? C11 O1 1.453(4) . . ? C11 O3 1.375(4) . . ? O1 C12 1.357(4) . . ? C12 O2 1.200(4) . . ? O3 C13 1.456(4) . . ? C13 C14 1.513(5) . . ? C13 C19 1.518(5) . . ? C14 C15 1.522(5) . . ? C15 C16 1.535(6) . . ? C15 C17 1.507(7) . . ? C17 C18 1.513(7) . . ? C18 C19 1.542(5) . . ? C19 C20 1.531(6) . . ? C20 C21 1.527(6) . . ? C20 C22 1.504(7) . . ? 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 ? ? ? ? ? ? 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 C1 C6 122.0(4) . . . ? C1 C2 C3 118.5(3) . . . ? C2 C3 C4 121.2(3) . . . ? C3 C4 C5 120.9(3) . . . ? C4 C5 C6 118.0(3) . . . ? C4 C5 N 122.2(3) . . . ? C6 C5 N 119.8(3) . . . ? C1 C6 C5 119.4(3) . . . ? C1 C6 C7 119.1(3) . . . ? C5 C6 C7 121.5(3) . . . ? C6 C7 C8 113.7(3) . . . ? C6 C7 C12 110.8(3) . . . ? C8 C7 C12 103.8(2) . . . ? C7 C8 C9 113.6(2) . . . ? C7 C8 C11 103.7(2) . . . ? C9 C8 C11 111.9(3) . . . ? C8 C9 N 110.2(3) . . . ? C5 N C9 115.2(3) . . . ? C5 N C10 119.2(3) . . . ? C9 N C10 114.7(3) . . . ? C8 C11 O1 106.2(3) . . . ? C8 C11 O3 110.8(2) . . . ? O1 C11 O3 110.1(2) . . . ? C11 O1 C12 109.9(2) . . . ? C7 C12 O1 110.8(3) . . . ? C7 C12 O2 128.7(3) . . . ? O1 C12 O2 120.5(3) . . . ? C11 O3 C13 115.5(2) . . . ? O3 C13 C14 110.5(3) . . . ? O3 C13 C19 106.9(3) . . . ? C14 C13 C19 112.3(3) . . . ? C13 C14 C15 112.1(3) . . . ? C14 C15 C16 111.1(4) . . . ? C14 C15 C17 108.6(4) . . . ? C16 C15 C17 113.5(4) . . . ? C15 C17 C18 112.4(4) . . . ? C17 C18 C19 112.2(3) . . . ? C13 C19 C18 108.7(3) . . . ? C13 C19 C20 113.5(3) . . . ? C18 C19 C20 113.5(3) . . . ? C19 C20 C21 112.2(4) . . . ? C19 C20 C22 113.9(3) . . . ? C21 C20 C22 110.0(4) . . . ?