# Copyright The Royal Society of Chemistry, 1999 # CCDC Number 1145/154 #=============================================================================== data_global #=============================================================================== _audit_creation_date 6-04-99 # 1. SUBMISSION DETAILS _publ_contact_author_name # Name of author for correspondance ; ; _publ_contact_author_address # Address of author for correspondance ; ; _publ_contact_author_phone 'xxxxxxxxxx' _publ_contact_author_fax 'xxxxxxxxxx' _publ_contact_author_email xxx@xx.xx.xx _publ_requested_journal 'J. Mater. Chem' _publ_contact_letter ; Please consider this CIF submission for publication as a new structure paper in Acta Crystallographica Section C. The figures, chemical structure diagram (scheme), Transfert of Copyright Agreement form and structure factors will be sent on receipt of your acknowledgement 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 ;Oligopyridine bis(nitronyl nitroxide) radicals: a full account on synthesis, structures, electrochemical, magnetic and electronic properties ; # 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 'Ulrich Gilles' ;Laboratoire de Chimie, d'Electronique et de Photonique Moleculaires Ecole Chimie Polymeres Materiaux (ECPM) Universite Louis Pasteur 1, rue Blaise Pascal 67008 Strasbourg France ; 'Lawson Raphael C.' ;Department of Chemistry University of Miami P.O. Box 249118 Coral Gables Florida 33124 USA ; 'Echegoyen Luis' ;Department of Chemistry University of Miami P.O. Box 249118 Coral Gables Florida 33124 USA ; 'Ziessel Raymond' ;Laboratoire de Chimie, d'Electronique et de Photonique Moleculaires Ecole Chimie Polymeres Materiaux (ECPM) Universite Louis Pasteur 1, rue Blaise Pascal 67008 Strasbourg France ; # 4. TEXT _publ_section_abstract ; ? ; _publ_section_comment ; ? ; _publ_section_exptl_prep ; ? ; _publ_section_exptl_refinement ; Backgrounds were obtained from analysis of the scan profile (Blessing, Coppens & Becker, 1974) ; _publ_section_references ; Blessing, R.H., Coppens, P. & Becker, P. (1974). J. Appl. Cryst., 7, 488-492. 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. Philips PW1100, Operation Manual, Eindhoven, 1974. Walker, N. & Stuart, D. (1983). Acta Cryst., A39, 158-166. ; _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_st547 #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C24 H30 N6 O4' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C24 H30 N6 O4' _chemical_formula_weight 466.54 _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 ? 0.017 0.009 International_Tables_Vol_IV_Table_2.3.1 H ? 0.000 0.000 International_Tables_Vol_IV_Table_2.3.1 N ? 0.029 0.018 International_Tables_Vol_IV_Table_2.3.1 O ? 0.047 0.032 International_Tables_Vol_IV_Table_2.3.1 #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' 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 _cell_length_a 17.216(5) _cell_length_b 10.832(3) _cell_length_c 6.247(2) _cell_angle_alpha 90 _cell_angle_beta 95.71(2) _cell_angle_gamma 90 _cell_volume 1159(1) _cell_formula_units_Z 2 _cell_measurement_temperature 173 _cell_measurement_reflns_used 24 _cell_measurement_theta_min 19.5 _cell_measurement_theta_max 20.5 _cell_special_details ; ? ; _exptl_crystal_description prism _exptl_crystal_colour 'green' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.34 _exptl_crystal_density_method 'none' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.765 _exptl_absorpt_correction_type refdelf_(Walker_&_Stuart,_1983) _exptl_absorpt_correction_T_min 0.8246 _exptl_absorpt_correction_T_max 1.0000 #=============================================================================== # 7. EXPERIMENTAL DATA _diffrn_special_details ; Maximum theta limited to 54 degrees by cooling device ; _diffrn_ambient_temperature 173 _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type Cu-K\a _diffrn_source xray_tube _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type Philips_PW1100 _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 -4 1 3 4 1 -1 0 -3 _diffrn_reflns_number 1469 _diffrn_reflns_av_R_equivalents 0 _diffrn_reflns_av_sigmaI/netI 0.333 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 3.0 _diffrn_reflns_theta_max 51.01 _reflns_number_total 1469 _reflns_number_gt 1025 _reflns_threshold_expression >3.0\s(I) _computing_data_collection 'Philips/PW1100/16 software 1976' _computing_cell_refinement CAD4_(Enraf-Nonius,_1994) _computing_data_reduction 'pwredu, local program' _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^)+0.0016 Fo^4^)+4.0' _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 1025 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.050 _refine_ls_R_factor_gt 0.040 _refine_ls_wR_factor_all 0.061 _refine_ls_wR_factor_ref 0.060 _refine_ls_goodness_of_fit_all 0.999 _refine_ls_goodness_of_fit_ref 1.113 _refine_ls_shift/su_max 0.000 _refine_ls_shift/esd_mean 0.000 _refine_diff_density_max 0.270 _refine_diff_density_min -0.183 #=============================================================================== # 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 0.5171(1) 0.0547(2) 0.5591(4) 0.036(1) Uani ? ? C C2 0.5465(2) 0.0433(2) 0.7670(4) 0.032(1) Uani ? ? C C3 0.5797(2) 0.1426(3) 0.8697(4) 0.042(2) Uani ? ? C C4 0.5851(2) 0.2546(2) 0.7692(4) 0.035(1) Uani ? ? C C5 0.5517(2) 0.2638(3) 0.5575(5) 0.044(2) Uani ? ? C N1 0.5179(1) 0.1638(2) 0.4501(4) 0.052(1) Uani ? ? N C6 0.6225(1) 0.3615(2) 0.8801(4) 0.036(1) Uani ? ? C N2 0.6136(1) 0.4807(2) 0.8235(3) 0.038(1) Uani ? ? N C7 0.6552(2) 0.5672(3) 0.9839(4) 0.039(2) Uani ? ? C C8 0.7127(2) 0.4778(2) 1.1118(4) 0.040(1) Uani ? ? C N3 0.6745(1) 0.3563(2) 1.0555(4) 0.042(1) Uani ? ? N O1 0.5676(1) 0.5224(2) 0.6677(3) 0.054(1) Uani ? ? O C9 0.5925(2) 0.6193(3) 1.1146(6) 0.065(2) Uani ? ? C C10 0.6922(2) 0.6711(3) 0.8660(5) 0.056(2) Uani ? ? C C11 0.7925(2) 0.4719(3) 1.0291(6) 0.062(2) Uani ? ? C C12 0.7209(2) 0.4931(3) 1.3528(5) 0.055(2) Uani ? ? C O2 0.6980(1) 0.2587(2) 1.1578(4) 0.063(1) Uani ? ? O H1 0.5439 -0.0334 0.8396 0.0428 Uiso calc C2 H H2 0.5999 0.1347 1.0161 0.0548 Uiso calc C3 H H3 0.5522 0.3411 0.4858 0.0584 Uiso calc C5 H H4 0.6156 0.6751 1.2196 0.0844 Uiso calc C9 H H5 0.5543 0.6616 1.0215 0.0844 Uiso calc C9 H H6 0.5683 0.5537 1.1842 0.0844 Uiso calc C9 H H7 0.7186 0.7258 0.9676 0.0747 Uiso calc C10 H H8 0.7285 0.6375 0.7766 0.0747 Uiso calc C10 H H9 0.6528 0.7149 0.7800 0.0747 Uiso calc C10 H H10 0.8195 0.5472 1.0607 0.0835 Uiso calc C11 H H11 0.8215 0.4055 1.0969 0.0835 Uiso calc C11 H H12 0.7866 0.4592 0.8779 0.0835 Uiso calc C11 H H13 0.7451 0.5701 1.3896 0.0755 Uiso calc C12 H H14 0.6707 0.4909 1.4035 0.0755 Uiso calc C12 H H15 0.7520 0.4280 1.4171 0.0755 Uiso calc C12 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 0.033(1) 0.032(1) 0.044(1) -0.004(1) 0.008(1) -0.003(1) C C2 0.043(1) 0.025(1) 0.029(1) -0.007(1) -0.003(1) 0.002(1) C C3 0.045(2) 0.041(2) 0.040(1) -0.003(1) 0.000(1) -0.001(1) C C4 0.032(1) 0.037(2) 0.037(1) -0.002(1) 0.000(1) -0.008(1) C C5 0.051(2) 0.038(2) 0.044(2) -0.009(1) -0.000(1) -0.001(1) C N1 0.056(2) 0.044(1) 0.055(1) -0.006(1) 0.003(1) -0.004(1) N C6 0.035(1) 0.035(1) 0.037(1) 0.001(1) 0.001(1) 0.000(1) C N2 0.038(1) 0.035(1) 0.040(1) -0.003(1) -0.005(1) 0.001(1) N C7 0.045(2) 0.035(1) 0.038(1) -0.005(1) 0.002(1) -0.008(1) C C8 0.044(2) 0.035(1) 0.040(1) -0.007(1) -0.001(1) -0.005(1) C N3 0.049(1) 0.033(1) 0.045(1) 0.001(1) -0.005(1) 0.001(1) N O1 0.062(1) 0.045(1) 0.058(1) -0.002(1) -0.020(1) 0.006(1) O C9 0.066(2) 0.053(2) 0.077(2) 0.005(2) 0.015(2) -0.018(2) C C10 0.071(2) 0.046(2) 0.054(2) -0.017(2) -0.003(2) -0.003(2) C C11 0.045(2) 0.069(2) 0.077(2) -0.007(2) 0.002(2) -0.007(2) C C12 0.078(2) 0.051(2) 0.042(2) -0.013(2) -0.009(2) -0.006(2) C O2 0.083(2) 0.042(1) 0.070(1) -0.002(1) -0.035(1) 0.006(1) O # 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 C1 1.488(6) . 3_656 ? C1 C2 1.352(4) . . ? C1 N1 1.364(4) . . ? C2 C3 1.349(4) . . ? C3 C4 1.374(4) . . ? C4 C5 1.392(4) . . ? C4 C6 1.465(4) . . ? C5 N1 1.372(4) . . ? C6 N2 1.344(4) . . ? C6 N3 1.345(4) . . ? N2 C7 1.501(3) . . ? N2 O1 1.275(3) . . ? C7 C8 1.548(4) . . ? C7 C9 1.526(4) . . ? C7 C10 1.519(4) . . ? C8 N3 1.498(4) . . ? C8 C11 1.517(5) . . ? C8 C12 1.507(4) . . ? N3 O2 1.280(3) . . ? 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 C1 C1 C2 119.7(3) . 3_656 . ? C1 C1 N1 117.8(3) . 3_656 . ? C2 C1 N1 122.5(2) . . . ? C1 C2 C3 118.9(2) . . . ? C2 C3 C4 122.1(3) . . . ? C3 C4 C5 117.1(2) . . . ? C3 C4 C6 121.9(3) . . . ? C5 C4 C6 120.9(2) . . . ? C4 C5 N1 121.5(3) . . . ? C1 N1 C5 117.7(3) . . . ? C4 C6 N2 127.0(2) . . . ? C4 C6 N3 125.3(3) . . . ? N2 C6 N3 107.7(2) . . . ? C6 N2 C7 112.9(2) . . . ? C6 N2 O1 126.0(2) . . . ? C7 N2 O1 120.5(2) . . . ? N2 C7 C8 101.1(2) . . . ? N2 C7 C9 105.7(2) . . . ? N2 C7 C10 109.5(2) . . . ? C8 C7 C9 113.9(2) . . . ? C8 C7 C10 115.9(2) . . . ? C9 C7 C10 109.8(3) . . . ? C7 C8 N3 100.7(2) . . . ? C7 C8 C11 113.9(3) . . . ? C7 C8 C12 115.9(2) . . . ? N3 C8 C11 105.9(2) . . . ? N3 C8 C12 109.0(2) . . . ? C11 C8 C12 110.3(3) . . . ? C6 N3 C8 113.3(2) . . . ? C6 N3 O2 126.4(2) . . . ? C8 N3 O2 119.9(2) . . . ? data_st566 #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C19 H27 N5 O4' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C19 H27 N5 O4' _chemical_formula_weight 389.46 _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 ? 0.017 0.009 International_Tables_Vol_IV_Table_2.3.1 H ? 0.000 0.000 International_Tables_Vol_IV_Table_2.3.1 N ? 0.029 0.018 International_Tables_Vol_IV_Table_2.3.1 O ? 0.047 0.032 International_Tables_Vol_IV_Table_2.3.1 #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' 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 _cell_length_a 16.334(5) _cell_length_b 10.316(3) _cell_length_c 11.990(3) _cell_angle_alpha 90 _cell_angle_beta 103.30(2) _cell_angle_gamma 90 _cell_volume 1966(1) _cell_formula_units_Z 4 _cell_measurement_temperature 173 _cell_measurement_reflns_used 24 _cell_measurement_theta_min 19.5 _cell_measurement_theta_max 20.5 _cell_special_details ; ? ; _exptl_crystal_description prism _exptl_crystal_colour 'violet' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.32 _exptl_crystal_density_method 'none' _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 0.775 _exptl_absorpt_correction_type refdelf_(Walker_&_Stuart,_1983) _exptl_absorpt_correction_T_min 0.6844 _exptl_absorpt_correction_T_max 1.0000 #=============================================================================== # 7. EXPERIMENTAL DATA _diffrn_special_details ; Maximum theta limited to 54 degrees by cooling device ; _diffrn_ambient_temperature 173 _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type Cu-K\a _diffrn_source xray_tube _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type Philips_PW1100 _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 4 3 2 6 -1 -4 -5 -2 2 _diffrn_reflns_number 2490 _diffrn_reflns_av_R_equivalents 0 _diffrn_reflns_av_sigmaI/netI 0.333 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.0 _diffrn_reflns_theta_max 52.07 _reflns_number_total 2490 _reflns_number_gt 1849 _reflns_threshold_expression >3.0\s(I) _computing_data_collection 'Philips/PW1100/16 software 1976' _computing_cell_refinement CAD4_(Enraf-Nonius,_1994) _computing_data_reduction 'pwredu, local program' _computing_structure_solution Direct_methods_(SIR,_Burla_et_al.,_1989) _computing_structure_refinement LSFM_MolEN_(Fair,_1990) _computing_molecular_graphics ? _computing_publication_material BTABLE_PTABLE_CIF_IN_MolEN_(Fair,_1990) #=============================================================================== # 8. REFINEMENT DATA _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme '4Fo^2^/(\s^2^(Fo^2^)+0.0009 Fo^4^)+3.0' _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 1849 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_abs_structure_details ; ? ; _refine_ls_R_factor_all 0.042 _refine_ls_R_factor_gt 0.033 _refine_ls_wR_factor_all 0.047 _refine_ls_wR_factor_ref 0.047 _refine_ls_goodness_of_fit_all 0.990 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_shift/su_max 0.026 _refine_ls_shift/esd_mean 0.004 _refine_diff_density_max 0.154 _refine_diff_density_min -0.153 #=============================================================================== # 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 O1 0.95627(9) 0.1543(2) 0.6126(1) 0.0458(9) Uani ? ? O O2 0.73301(9) -0.0221(2) 0.7349(1) 0.0386(8) Uani ? ? O O3 0.76826(9) 0.5185(2) 0.8577(1) 0.0414(9) Uani ? ? O O4 0.51347(9) 0.4212(2) 0.6147(1) 0.0403(9) Uani ? ? O N1 0.7427(1) 0.2722(2) 0.6902(1) 0.0305(9) Uani ? ? N N2 0.9123(1) 0.0766(2) 0.6580(1) 0.0325(9) Uani ? ? N N3 0.8069(1) -0.0047(2) 0.7193(1) 0.0302(9) Uani ? ? N N4 0.6902(1) 0.5172(2) 0.8109(1) 0.0306(9) Uani ? ? N N5 0.5692(1) 0.4765(2) 0.6922(1) 0.0309(9) Uani ? ? N C1 0.7823(1) 0.2098(2) 0.6196(2) 0.030(1) Uani ? ? C C2 0.7766(1) 0.2445(2) 0.5063(2) 0.033(1) Uani ? ? C C3 0.7252(1) 0.3462(2) 0.4614(2) 0.038(1) Uani ? ? C C4 0.6824(1) 0.4100(2) 0.5313(2) 0.038(1) Uani ? ? C C5 0.6939(1) 0.3718(2) 0.6442(2) 0.031(1) Uani ? ? C C6 0.8331(1) 0.0968(2) 0.6667(2) 0.029(1) Uani ? ? C C7 0.9430(1) -0.0564(2) 0.6966(2) 0.036(1) Uani ? ? C C8 0.8782(1) -0.0953(2) 0.7680(2) 0.033(1) Uani ? ? C C9 0.9344(2) -0.1362(3) 0.5877(2) 0.059(1) Uani ? ? C C10 1.0337(2) -0.0511(3) 0.7626(3) 0.055(2) Uani ? ? C C11 0.8487(1) -0.2335(3) 0.7551(2) 0.049(1) Uani ? ? C C12 0.9063(2) -0.0597(3) 0.8944(2) 0.055(2) Uani ? ? C C13 0.6521(1) 0.4490(2) 0.7191(2) 0.030(1) Uani ? ? C C14 0.6268(1) 0.5905(2) 0.8609(2) 0.033(1) Uani ? ? C C15 0.5515(1) 0.5950(2) 0.7554(2) 0.032(1) Uani ? ? C C16 0.6100(1) 0.5083(3) 0.9579(2) 0.040(1) Uani ? ? C C17 0.6608(1) 0.7218(3) 0.9046(2) 0.045(1) Uani ? ? C C18 0.4655(1) 0.5888(3) 0.7812(2) 0.042(1) Uani ? ? C C19 0.5556(2) 0.7076(2) 0.6743(2) 0.045(1) Uani ? ? C H1 0.8076 0.1989 0.4607 0.0428 Uiso calc C2 H H2 0.7194 0.3720 0.3839 0.0494 Uiso calc C3 H H3 0.6454 0.4794 0.5022 0.0494 Uiso calc C4 H H4 0.9532 -0.2222 0.6072 0.0748 Uiso calc C9 H H5 0.8771 -0.1378 0.5472 0.0748 Uiso calc C9 H H6 0.9676 -0.0984 0.5408 0.0748 Uiso calc C9 H H7 1.0524 -0.1359 0.7866 0.0785 Uiso calc C10 H H8 1.0675 -0.0169 0.7148 0.0785 Uiso calc C10 H H9 1.0382 0.0030 0.8279 0.0785 Uiso calc C10 H H10 0.8944 -0.2896 0.7862 0.0653 Uiso calc C11 H H11 0.8052 -0.2457 0.7946 0.0653 Uiso calc C11 H H12 0.8280 -0.2526 0.6761 0.0653 Uiso calc C11 H H13 0.8644 -0.0857 0.9332 0.0755 Uiso calc C12 H H14 0.9577 -0.1025 0.9271 0.0755 Uiso calc C12 H H15 0.9142 0.0314 0.9016 0.0755 Uiso calc C12 H H16 0.5702 0.5508 0.9919 0.0541 Uiso calc C16 H H17 0.5882 0.4265 0.9287 0.0541 Uiso calc C16 H H18 0.6609 0.4959 1.0138 0.0541 Uiso calc C16 H H19 0.6202 0.7662 0.9355 0.0583 Uiso calc C17 H H20 0.7109 0.7109 0.9624 0.0583 Uiso calc C17 H H21 0.6728 0.7708 0.8431 0.0583 Uiso calc C17 H H22 0.4562 0.6650 0.8211 0.0556 Uiso calc C18 H H23 0.4239 0.5827 0.7115 0.0556 Uiso calc C18 H H24 0.4622 0.5150 0.8273 0.0556 Uiso calc C18 H H25 0.5449 0.7866 0.7091 0.0593 Uiso calc C19 H H26 0.6100 0.7108 0.6586 0.0593 Uiso calc C19 H H27 0.5146 0.6956 0.6048 0.0593 Uiso calc C19 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 O1 0.0426(8) 0.0389(9) 0.0579(9) -0.0036(7) 0.0185(7) 0.0060(8) O O2 0.0326(7) 0.0431(9) 0.0411(8) 0.0004(7) 0.0113(6) 0.0038(8) O O3 0.0345(8) 0.0452(9) 0.0455(9) 0.0001(7) 0.0053(7) -0.0017(8) O O4 0.0407(8) 0.0464(9) 0.0345(8) -0.0015(8) 0.0013(7) -0.0032(8) O N1 0.0349(9) 0.0299(9) 0.0272(9) 0.0004(8) 0.0063(7) -0.0008(8) N N2 0.0331(9) 0.0296(9) 0.0350(9) -0.0006(8) 0.0110(7) 0.0020(8) N N3 0.0279(8) 0.034(1) 0.0290(9) 0.0016(8) 0.0069(7) 0.0011(8) N N4 0.0293(9) 0.032(1) 0.0307(9) 0.0009(8) 0.0062(7) 0.0010(8) N N5 0.0338(9) 0.032(1) 0.0271(9) 0.0003(8) 0.0046(7) 0.0006(8) N C1 0.031(1) 0.029(1) 0.030(1) -0.002(1) 0.0070(9) -0.002(1) C C2 0.036(1) 0.036(1) 0.027(1) 0.002(1) 0.0086(9) -0.003(1) C C3 0.045(1) 0.041(1) 0.029(1) 0.004(1) 0.0113(9) 0.007(1) C C4 0.044(1) 0.034(1) 0.036(1) 0.009(1) 0.010(1) 0.006(1) C C5 0.034(1) 0.029(1) 0.030(1) 0.002(1) 0.0075(9) 0.003(1) C C6 0.032(1) 0.029(1) 0.025(1) -0.0008(9) 0.0057(9) -0.0021(9) C C7 0.034(1) 0.029(1) 0.045(1) 0.003(1) 0.010(1) 0.006(1) C C8 0.031(1) 0.035(1) 0.035(1) 0.003(1) 0.0054(9) 0.005(1) C C9 0.080(2) 0.040(1) 0.064(1) 0.008(1) 0.039(1) 0.001(1) C C10 0.039(1) 0.046(1) 0.095(2) 0.003(1) 0.013(1) 0.023(1) C C11 0.042(1) 0.036(1) 0.075(2) 0.003(1) 0.019(1) 0.010(1) C C12 0.058(2) 0.072(2) 0.041(1) 0.014(1) 0.004(1) 0.010(1) C C13 0.034(1) 0.028(1) 0.027(1) 0.001(1) 0.0070(9) 0.003(1) C C14 0.031(1) 0.035(1) 0.032(1) 0.002(1) 0.0092(9) -0.001(1) C C15 0.034(1) 0.031(1) 0.031(1) 0.004(1) 0.0072(9) -0.002(1) C C16 0.041(1) 0.054(1) 0.029(1) 0.004(1) 0.007(1) 0.002(1) C C17 0.040(1) 0.045(1) 0.050(1) -0.000(1) 0.011(1) -0.013(1) C C18 0.039(1) 0.050(1) 0.039(1) 0.007(1) 0.007(1) -0.003(1) C C19 0.059(1) 0.038(1) 0.041(1) 0.011(1) 0.012(1) 0.007(1) 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 O1 N2 1.278(3) . . ? O2 N3 1.277(2) . . ? O3 N4 1.269(2) . . ? O4 N5 1.277(2) . . ? N1 C1 1.342(3) . . ? N1 C5 1.339(3) . . ? N2 C6 1.338(3) . . ? N2 C7 1.497(3) . . ? N3 C6 1.342(3) . . ? N3 C8 1.503(3) . . ? N4 C13 1.335(3) . . ? N4 C14 1.513(3) . . ? N5 C13 1.347(3) . . ? N5 C15 1.501(3) . . ? C1 C2 1.387(3) . . ? C1 C6 1.467(3) . . ? C2 C3 1.374(3) . . ? C3 C4 1.376(4) . . ? C4 C5 1.380(3) . . ? C5 C13 1.479(3) . . ? C7 C8 1.560(3) . . ? C7 C9 1.522(4) . . ? C7 C10 1.512(3) . . ? C8 C11 1.501(3) . . ? C8 C12 1.523(3) . . ? C14 C15 1.549(3) . . ? C14 C16 1.514(3) . . ? C14 C17 1.512(3) . . ? C15 C18 1.507(3) . . ? C15 C19 1.527(3) . . ? 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 C1 N1 C5 115.8(2) . . . ? O1 N2 C6 125.8(2) . . . ? O1 N2 C7 121.6(2) . . . ? C6 N2 C7 112.3(2) . . . ? O2 N3 C6 126.4(2) . . . ? O2 N3 C8 122.0(2) . . . ? C6 N3 C8 111.5(2) . . . ? O3 N4 C13 126.9(2) . . . ? O3 N4 C14 122.0(2) . . . ? C13 N4 C14 111.0(2) . . . ? O4 N5 C13 126.1(2) . . . ? O4 N5 C15 122.9(2) . . . ? C13 N5 C15 110.6(2) . . . ? N1 C1 C2 124.1(2) . . . ? N1 C1 C6 116.8(2) . . . ? C2 C1 C6 119.1(2) . . . ? C1 C2 C3 118.6(2) . . . ? C2 C3 C4 118.4(2) . . . ? C3 C4 C5 119.2(2) . . . ? N1 C5 C4 123.8(2) . . . ? N1 C5 C13 118.5(2) . . . ? C4 C5 C13 117.7(2) . . . ? N2 C6 N3 109.5(2) . . . ? N2 C6 C1 124.4(2) . . . ? N3 C6 C1 126.1(2) . . . ? N2 C7 C8 100.6(2) . . . ? N2 C7 C9 105.8(2) . . . ? N2 C7 C10 110.3(2) . . . ? C8 C7 C9 113.0(2) . . . ? C8 C7 C10 115.4(2) . . . ? C9 C7 C10 110.8(2) . . . ? N3 C8 C7 100.9(2) . . . ? N3 C8 C11 110.4(2) . . . ? N3 C8 C12 105.4(2) . . . ? C7 C8 C11 115.4(2) . . . ? C7 C8 C12 113.4(2) . . . ? C11 C8 C12 110.4(2) . . . ? N4 C13 N5 109.7(2) . . . ? N4 C13 C5 126.3(2) . . . ? N5 C13 C5 123.2(2) . . . ? N4 C14 C15 100.3(2) . . . ? N4 C14 C16 106.6(2) . . . ? N4 C14 C17 110.7(2) . . . ? C15 C14 C16 113.2(2) . . . ? C15 C14 C17 114.6(2) . . . ? C16 C14 C17 110.7(2) . . . ? N5 C15 C14 100.3(2) . . . ? N5 C15 C18 111.5(2) . . . ? N5 C15 C19 104.8(2) . . . ? C14 C15 C18 115.7(2) . . . ? C14 C15 C19 113.5(2) . . . ? C18 C15 C19 110.1(2) . . . ? data_st604 #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C19 H27 N5 O4' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C19 H27 N5 O4' _chemical_formula_weight 389.46 _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 ? 0.017 0.009 International_Tables_Vol_IV_Table_2.3.1 H ? 0.000 0.000 International_Tables_Vol_IV_Table_2.3.1 N ? 0.029 0.018 International_Tables_Vol_IV_Table_2.3.1 O ? 0.047 0.032 International_Tables_Vol_IV_Table_2.3.1 #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' 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 _cell_length_a 6.192(2) _cell_length_b 11.794(3) _cell_length_c 13.513(4) _cell_angle_alpha 90 _cell_angle_beta 93.74(2) _cell_angle_gamma 90 _cell_volume 984.7(9) _cell_formula_units_Z 2 _cell_measurement_temperature 173 _cell_measurement_reflns_used 24 _cell_measurement_theta_min 19.5 _cell_measurement_theta_max 20.5 _cell_special_details ; ? ; _exptl_crystal_description prism _exptl_crystal_colour 'violet' _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.31 _exptl_crystal_density_method 'none' _exptl_crystal_F_000 416 _exptl_absorpt_coefficient_mu 0.773 _exptl_absorpt_correction_type refdelf_(Walker_&_Stuart,_1983) _exptl_absorpt_correction_T_min 0.7237 _exptl_absorpt_correction_T_max 1.0000 #=============================================================================== # 7. EXPERIMENTAL DATA _diffrn_special_details ; Maximum theta limited to 54 degrees by cooling device ; _diffrn_ambient_temperature 173 _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type Cu-K\a _diffrn_source xray_tube _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type Philips_PW1100 _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 2 -3 2 0 6 0 -2 3 -2 _diffrn_reflns_number 1188 _diffrn_reflns_av_R_equivalents 0 _diffrn_reflns_av_sigmaI/netI 0.333 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.0 _diffrn_reflns_theta_max 51.05 _reflns_number_total 1188 _reflns_number_gt 966 _reflns_threshold_expression >3.0\s(I) _computing_data_collection 'Philips/PW1100/16 software 1976' _computing_cell_refinement CAD4_(Enraf-Nonius,_1994) _computing_data_reduction 'pwredu, local program' _computing_structure_solution Direct_methods_(SIR,_Burla_et_al.,_1989) _computing_structure_refinement LSFM_MolEN_(Fair,_1990) _computing_molecular_graphics ? _computing_publication_material BTABLE_PTABLE_CIF_IN_MolEN_(Fair,_1990) #=============================================================================== # 8. REFINEMENT DATA _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme '4Fo^2^/(\s^2^(Fo^2^)+0.0016 Fo^4^)+4.0' _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 966 _refine_ls_number_parameters 127 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_abs_structure_details ; ? ; _refine_ls_R_factor_all 0.050 _refine_ls_R_factor_gt 0.045 _refine_ls_wR_factor_all 0.078 _refine_ls_wR_factor_ref 0.078 _refine_ls_goodness_of_fit_all 1.481 _refine_ls_goodness_of_fit_ref 1.586 _refine_ls_shift/su_max 0.001 _refine_ls_shift/esd_mean 0.000 _refine_diff_density_max 0.554 _refine_diff_density_min -0.234 #=============================================================================== # 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_occupancy _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom _atom_site_type_symbol C1 0.8414(4) 0.1876(2) 0.8886(2) 0.031(1) 1.000 Uani ? ? C N1 0.9185(3) 0.2949(2) 0.8965(2) 0.035(1) 1.000 Uani ? ? N C2 0.7723(4) 0.3768(2) 0.8394(2) 0.036(1) 1.000 Uani ? ? C C3 0.6539(4) 0.2950(2) 0.7646(2) 0.036(1) 1.000 Uani ? ? C N2 0.6766(3) 0.1857(2) 0.8202(2) 0.036(1) 1.000 Uani ? ? N O1 1.0749(3) 0.3286(2) 0.9555(1) 0.049(1) 1.000 Uani ? ? O C4 0.6283(5) 0.4278(3) 0.9135(2) 0.049(2) 1.000 Uani ? ? C C5 0.9050(5) 0.4704(3) 0.7952(2) 0.051(2) 1.000 Uani ? ? C C6 0.7698(6) 0.2768(3) 0.6698(2) 0.060(2) 1.000 Uani ? ? C C7 0.4167(5) 0.3203(3) 0.7409(2) 0.051(2) 1.000 Uani ? ? C O2 0.5651(3) 0.0991(2) 0.7925(2) 0.057(1) 1.000 Uani ? ? O C8 0.9243(4) 0.0908(2) 0.9466(2) 0.031(1) 1.000 Uani ? ? C C9 1.1442(4) 0.0820(2) 0.9743(2) 0.037(1) 1.000 Uani ? ? C N3 0.7812(4) 0.0095(2) 0.9719(2) 0.042(1) 0.930 Uani ? ? N H1 0.5320 0.4806 0.8810 0.0648 1.000 Uiso calc C4 H H2 0.5474 0.3693 0.9423 0.0648 1.000 Uiso calc C4 H H3 0.7148 0.4655 0.9640 0.0648 1.000 Uiso calc C4 H H4 0.8110 0.5216 0.7593 0.0686 1.000 Uiso calc C5 H H5 0.9842 0.5099 0.8469 0.0686 1.000 Uiso calc C5 H H6 1.0027 0.4380 0.7517 0.0686 1.000 Uiso calc C5 H H7 0.7609 0.3440 0.6310 0.0805 1.000 Uiso calc C6 H H8 0.9174 0.2591 0.6863 0.0805 1.000 Uiso calc C6 H H9 0.7033 0.2160 0.6331 0.0805 1.000 Uiso calc C6 H H10 0.4024 0.3898 0.7055 0.0687 1.000 Uiso calc C7 H H11 0.3534 0.2608 0.7014 0.0687 1.000 Uiso calc C7 H H12 0.3453 0.3261 0.8008 0.0687 1.000 Uiso calc C7 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 0.034(1) 0.028(1) 0.031(1) 0.001(1) -0.002(1) 0.000(1) C N1 0.037(1) 0.030(1) 0.038(1) -0.001(1) -0.004(1) 0.004(1) N C2 0.038(1) 0.030(1) 0.041(1) 0.005(1) -0.002(1) 0.006(1) C C3 0.042(1) 0.033(1) 0.034(1) 0.004(1) -0.002(1) 0.008(1) C N2 0.042(1) 0.029(1) 0.039(1) -0.003(1) -0.006(1) -0.000(1) N O1 0.051(1) 0.037(1) 0.063(1) -0.0059(9) -0.020(1) 0.004(1) O C4 0.056(2) 0.039(2) 0.054(2) 0.010(1) 0.004(2) -0.004(1) C C5 0.049(2) 0.039(2) 0.069(2) 0.001(1) -0.003(2) 0.020(2) C C6 0.081(2) 0.065(2) 0.041(2) 0.003(2) 0.008(2) 0.006(2) C C7 0.049(2) 0.043(2) 0.064(2) 0.002(2) -0.015(2) 0.008(2) C O2 0.074(1) 0.038(1) 0.066(1) -0.009(1) -0.029(1) 0.004(1) O C8 0.043(1) 0.026(1) 0.026(1) -0.000(1) 0.002(1) 0.000(1) C C9 0.042(1) 0.035(1) 0.035(1) 0.009(1) -0.006(1) 0.001(1) C N3 0.050(1) 0.037(1) 0.042(1) 0.006(1) -0.002(1) 0.000(1) N # 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 N1 1.356(3) . . ? C1 N2 1.331(4) . . ? C1 C8 1.458(4) . . ? N1 C2 1.503(3) . . ? N1 O1 1.277(3) . . ? C2 C3 1.547(4) . . ? C2 C4 1.511(4) . . ? C2 C5 1.520(4) . . ? C3 N2 1.495(3) . . ? C3 C6 1.519(4) . . ? C3 C7 1.516(4) . . ? N2 O2 1.275(3) . . ? C8 C9 1.391(4) . . ? C8 N3 1.363(4) . . ? C9 N3 1.367(4) . 3_757 ? 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 N1 C1 N2 108.6(2) . . . ? N1 C1 C8 125.4(2) . . . ? N2 C1 C8 125.9(2) . . . ? C1 N1 C2 111.3(2) . . . ? C1 N1 O1 126.0(2) . . . ? C2 N1 O1 121.9(2) . . . ? N1 C2 C3 100.2(2) . . . ? N1 C2 C4 106.1(2) . . . ? N1 C2 C5 110.2(2) . . . ? C3 C2 C4 114.1(2) . . . ? C3 C2 C5 116.1(2) . . . ? C4 C2 C5 109.3(3) . . . ? C2 C3 N2 100.7(2) . . . ? C2 C3 C6 114.3(2) . . . ? C2 C3 C7 115.2(2) . . . ? N2 C3 C6 105.6(2) . . . ? N2 C3 C7 109.4(2) . . . ? C6 C3 C7 110.6(2) . . . ? C1 N2 C3 112.2(2) . . . ? C1 N2 O2 126.3(2) . . . ? C3 N2 O2 120.8(2) . . . ? C1 C8 C9 120.4(2) . . . ? C1 C8 N3 118.2(2) . . . ? C9 C8 N3 121.4(2) . . . ? C8 C9 N3 119.5(3) . . 3_757 ? C8 N3 C9 119.0(2) . . 3_757 ?