# Copyright The Royal Society of Chemistry, 1999 # CCDC Number: 1145/136 #=============================================================================== data_global #=============================================================================== _audit_creation_date 26-11-98 # 1. SUBMISSION DETAILS _publ_contact_author_name # Name of author for correspondance ; Prof. Jean Fischer ; _publ_contact_author_address # Address of author for correspondance ; Universite Louis Pasteur Laboratoire de Cristallochimie et de Chimie Structurale 4, rue Blaise Pascal 67070 Strasbourg France ; _publ_contact_author_phone '+33 (0)3 88 41 60 58' _publ_contact_author_fax '+33 (0)3 88 41 53 63' _publ_contact_author_email fischer@chimie.u-strasbg.fr _publ_requested_journal 'Journal of Material Chemistry' _publ_contact_letter ; To account for referee's comments we need to replace the cif's for the paper referenced below by the following cif's. Regards, Jean ; _publ_requested_category FM #=============================================================================== # 3. TITLE AND AUTHOR LIST _publ_section_title ; Synthesis, structure and properties of benzoic acids bearing para-, or meta- imino nitroxides or ortho-nitronyl nitroxide radical centres. ; # 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 ; 'Stroh Christophe' ;Laboratoire de Chimie,d'Electronique Moleculaires,ECPM Universite Louis Pasteur 1, rue Blaise Pascal 67008 Strasbourg Cedex France ; 'Romero Francisco' ;Laboratoire de Chimie,d'Electronique Moleculaires,ECPM Universite Louis Pasteur 1, rue Blaise Pascal 67008 Strasbourg Cedex France ; 'Kyritsakas Nathalie' ;Universite Louis Pasteur Laboratoire de Cristallochimie et de Chimie Structurale 4, rue Blaise Pascal 67070 Strasbourg France ; 'Catala Laure' ;Institut Charles Sadron Universite Louis Pasteur 6, rue Boussingault 67083 Strasbourg Cedex France ; 'Turek Philippe' ;Institut de Physique et Chimie des Materiaux Universite Louis Pasteur 23, rue du Loess 67037 Strasbourg Cedex France ; 'Ziessel Raymond' ;Laboratoire de Chimie,d'Electronique Moleculaires,ECPM Universite Louis Pasteur 1, rue Blaise Pascal 67008 Strasbourg Cedex 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_pIMBAH #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C14 H19 N2 O4' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C14 H19 N2 O4' _chemical_formula_weight 279.32 _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 20.403(6) _cell_length_b 10.402(3) _cell_length_c 6.824(2) _cell_angle_alpha 90 _cell_angle_beta 96.69(2) _cell_angle_gamma 90 _cell_volume 1438(1) _cell_formula_units_Z 4 _cell_measurement_temperature 173 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 19.5 _cell_measurement_theta_max 20.5 _cell_special_details ; ? ; _exptl_crystal_description prism _exptl_crystal_colour 'red' _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.29 _exptl_crystal_density_method 'none' _exptl_crystal_F_000 596 _exptl_absorpt_coefficient_mu 0.788 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? #=============================================================================== # 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 60 _diffrn_standards_decay_% 0 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 6 -2 -2 7 2 1 -1 1 3 _diffrn_reflns_number 1850 _diffrn_reflns_av_R_equivalents 0 _diffrn_reflns_av_sigmaI/netI 0.333 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _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 2.0 _diffrn_reflns_theta_max 26.0 _reflns_number_total 1850 _reflns_number_gt 1342 _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 1342 _refine_ls_number_parameters 181 _refine_ls_number_restraints 12 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.046 _refine_ls_R_factor_gt 0.039 _refine_ls_wR_factor_all 0.058 _refine_ls_wR_factor_ref 0.058 _refine_ls_goodness_of_fit_all 0.994 _refine_ls_goodness_of_fit_ref 1.105 _refine_ls_shift/su_max 0.005 _refine_ls_shift/esd_mean 0.001 _refine_diff_density_max 0.422 _refine_diff_density_min -0.352 #=============================================================================== # 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 0.8884(1) -0.1010(2) 0.4200(3) 0.037(1) Uani ? ? C C2 0.9008(1) -0.0991(2) 0.2247(3) 0.041(1) Uani ? ? C C3 0.9261(1) 0.0095(2) 0.1460(3) 0.041(1) Uani ? ? C C4 0.9383(1) 0.1188(2) 0.2577(3) 0.039(1) Uani ? ? C C5 0.9266(1) 0.1170(2) 0.4537(4) 0.046(1) Uani ? ? C C6 0.9019(1) 0.0086(2) 0.5343(3) 0.046(1) Uani ? ? C C7 0.9636(1) 0.2377(2) 0.1723(3) 0.046(1) Uani ? ? C O1 0.97452(9) 0.2267(2) -0.0116(3) 0.063(1) Uani ? ? O O2 0.9729(1) 0.3359(2) 0.2655(3) 0.070(1) Uani ? ? O C8 0.8606(1) -0.2203(2) 0.4941(3) 0.037(1) Uani ? ? C N1 0.82647(9) -0.2251(2) 0.6587(3) 0.041(1) Uani ? ? N C9 0.7897(1) -0.3489(2) 0.6597(3) 0.041(1) Uani ? ? C C10 0.8296(1) -0.4287(2) 0.5237(3) 0.045(1) Uani ? ? C N2 0.86211(9) -0.3305(2) 0.4080(3) 0.045(1) Uani ? ? N O3 0.81890(8) -0.1344(2) 0.7782(2) 0.0574(9) Uani ? ? O C11 0.7896(1) -0.3962(2) 0.8696(4) 0.056(1) Uani ? ? C C12 0.7195(1) -0.3190(3) 0.5706(4) 0.061(2) Uani ? ? C C13 0.8854(1) -0.5054(3) 0.6373(4) 0.061(2) Uani ? ? C C14 0.7886(1) -0.5174(3) 0.3818(4) 0.066(2) Uani ? ? C OW 1.04193(8) 0.4068(2) -0.1534(2) 0.059(1) Uani ? ? O H01 0.9981 0.3064 -0.0758 0.0814 Uiso ? ? H H02 1.0283 0.4898 -0.1970 0.0769 Uiso ? ? H H03 1.0696 0.3823 -0.2578 0.0769 Uiso ? ? H H1 0.8918 -0.1732 0.1446 0.0542 Uiso calc C2 H H2 0.9353 0.0089 0.0126 0.0536 Uiso calc C3 H H3 0.9358 0.1913 0.5331 0.0607 Uiso calc C5 H H4 0.8940 0.0086 0.6687 0.0608 Uiso calc C6 H H5 0.7661 -0.4751 0.8692 0.0725 Uiso calc C11 H H6 0.8338 -0.4091 0.9274 0.0725 Uiso calc C11 H H7 0.7689 -0.3341 0.9440 0.0725 Uiso calc C11 H H8 0.6936 -0.3950 0.5675 0.0826 Uiso calc C12 H H9 0.7011 -0.2558 0.6485 0.0826 Uiso calc C12 H H10 0.7199 -0.2874 0.4401 0.0826 Uiso calc C12 H H11 0.8673 -0.5698 0.7139 0.0786 Uiso calc C13 H H12 0.9112 -0.5449 0.5468 0.0786 Uiso calc C13 H H13 0.9124 -0.4494 0.7218 0.0786 Uiso calc C13 H H14 0.7677 -0.5802 0.4544 0.0867 Uiso calc C14 H H15 0.7560 -0.4687 0.3034 0.0867 Uiso calc C14 H H16 0.8163 -0.5588 0.2988 0.0867 Uiso calc C14 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 0.031(1) 0.042(1) 0.040(1) 0.001(1) -0.004(1) -0.000(1) C C2 0.041(1) 0.042(1) 0.041(1) -0.002(1) -0.004(1) -0.002(1) C C3 0.040(1) 0.045(1) 0.037(1) -0.001(1) -0.000(1) 0.002(1) C C4 0.033(1) 0.039(1) 0.045(1) -0.000(1) -0.001(1) -0.001(1) C C5 0.050(1) 0.042(1) 0.047(1) -0.004(1) 0.001(1) -0.006(1) C C6 0.051(1) 0.051(1) 0.037(1) -0.003(1) 0.002(1) -0.001(1) C C7 0.044(1) 0.045(1) 0.049(1) 0.001(1) 0.007(1) -0.001(1) C O1 0.083(1) 0.052(1) 0.0590(9) -0.0137(9) 0.0234(9) -0.0003(9) O O2 0.104(1) 0.047(1) 0.068(1) -0.018(1) 0.029(1) -0.0086(9) O C8 0.037(1) 0.043(1) 0.033(1) -0.002(1) -0.002(1) -0.002(1) C N1 0.041(1) 0.045(1) 0.038(1) -0.0016(9) 0.0008(8) -0.0034(9) N C9 0.037(1) 0.047(1) 0.040(1) -0.007(1) 0.000(1) 0.001(1) C C10 0.051(1) 0.043(1) 0.041(1) -0.008(1) 0.004(1) 0.002(1) C N2 0.050(1) 0.044(1) 0.040(1) -0.0063(9) 0.0045(9) -0.0002(9) N O3 0.067(1) 0.0546(9) 0.0518(9) -0.0049(9) 0.0158(8) -0.0118(9) O C11 0.060(1) 0.059(2) 0.049(1) -0.007(1) 0.009(1) 0.003(1) C C12 0.045(1) 0.069(2) 0.075(2) -0.005(1) -0.001(1) 0.006(2) C C13 0.064(2) 0.051(1) 0.068(2) 0.005(1) 0.015(1) 0.010(1) C C14 0.087(2) 0.059(2) 0.055(1) -0.028(1) 0.014(1) -0.007(1) C OW 0.064(1) 0.0501(9) 0.064(1) 0.0035(8) 0.0217(8) 0.0105(8) 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 C2 1.386(3) . . ? C1 C6 1.390(3) . . ? C1 C8 1.477(3) . . ? C2 C3 1.377(3) . . ? C3 C4 1.375(3) . . ? C4 C5 1.386(4) . . ? C4 C7 1.485(4) . . ? C5 C6 1.377(4) . . ? C7 O1 1.305(3) . . ? C7 O2 1.207(3) . . ? O1 H01 1.0770 . . ? C8 N1 1.389(3) . . ? C8 N2 1.291(3) . . ? N1 C9 1.491(3) . . ? N1 O3 1.268(2) . . ? C9 C10 1.546(4) . . ? C9 C11 1.515(4) . . ? C9 C12 1.522(4) . . ? C10 N2 1.493(3) . . ? C10 C13 1.526(4) . . ? C10 C14 1.517(4) . . ? OW H01 1.5101 . . ? OW H02 0.9442 . . ? OW H03 0.9930 . . ? H02 H03 1.4878 . . ? 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 118.8(2) . . . ? C2 C1 C8 117.5(2) . . . ? C6 C1 C8 123.7(2) . . . ? C1 C2 C3 120.4(2) . . . ? C2 C3 C4 120.9(2) . . . ? C3 C4 C5 119.0(2) . . . ? C3 C4 C7 121.3(2) . . . ? C5 C4 C7 119.7(2) . . . ? C4 C5 C6 120.6(2) . . . ? C1 C6 C5 120.4(2) . . . ? C4 C7 O1 114.2(2) . . . ? C4 C7 O2 122.6(2) . . . ? O1 C7 O2 123.1(2) . . . ? C7 O1 H01 117.30 . . . ? C1 C8 N1 123.7(2) . . . ? C1 C8 N2 124.1(2) . . . ? N1 C8 N2 112.1(2) . . . ? C8 N1 C9 109.6(2) . . . ? C8 N1 O3 127.1(2) . . . ? C9 N1 O3 122.7(2) . . . ? N1 C9 C10 99.2(2) . . . ? N1 C9 C11 109.9(2) . . . ? N1 C9 C12 105.8(2) . . . ? C10 C9 C11 116.9(2) . . . ? C10 C9 C12 114.0(2) . . . ? C11 C9 C12 109.9(2) . . . ? C9 C10 N2 104.3(2) . . . ? C9 C10 C13 112.9(2) . . . ? C9 C10 C14 114.8(2) . . . ? N2 C10 C13 106.0(2) . . . ? N2 C10 C14 109.0(2) . . . ? C13 C10 C14 109.2(2) . . . ? C8 N2 C10 109.4(2) . . . ? H01 OW H02 125.33 . . . ? H01 OW H03 118.91 . . . ? H02 OW H03 100.32 . . . ? O1 H01 OW 170.34 . . . ? OW H02 H03 41.04 . . . ? OW H03 H02 38.64 . . . ? #=============================================================================== data_m-IMBAH #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C14 H17 N2 O3' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C14 H17 N2 O3' _chemical_formula_weight 261.30 _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 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 6.916(2) _cell_length_b 20.003(6) _cell_length_c 10.165(3) _cell_angle_alpha 90 _cell_angle_beta 106.68(2) _cell_angle_gamma 90 _cell_volume 1347(1) _cell_formula_units_Z 4 _cell_measurement_temperature 294 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 19.0 _cell_measurement_theta_max 20.5 _cell_special_details ; ? ; _exptl_crystal_description prism _exptl_crystal_colour 'red' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.29 _exptl_crystal_density_method 'none' _exptl_crystal_F_000 556 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? #=============================================================================== # 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 1 5 -4 2 1 3 2 4 -3 _diffrn_reflns_number 3268 _diffrn_reflns_av_R_equivalents 0.040 _diffrn_reflns_av_sigmaI/netI 0.333 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.5 _diffrn_reflns_theta_max 26.97 _reflns_number_total 3024 _reflns_number_gt 1361 _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 1361 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_abs_structure_details ; ? ; _refine_ls_R_factor_all 0.145 _refine_ls_R_factor_gt 0.043 _refine_ls_wR_factor_all 0.095 _refine_ls_wR_factor_ref 0.055 _refine_ls_goodness_of_fit_all 1.728 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_shift/su_max 0.001 _refine_ls_shift/esd_mean 0.000 _refine_diff_density_max 0.141 _refine_diff_density_min -0.207 #=============================================================================== # 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 0.1678(4) 0.0692(1) 0.6824(2) 0.035(1) Uani ? ? C N1 0.1775(3) 0.0906(1) 0.5530(2) 0.042(1) Uani ? ? N O1 0.2553(3) 0.0587(1) 0.4734(2) 0.062(1) Uani ? ? O C2 0.0915(4) 0.1594(1) 0.5265(3) 0.038(1) Uani ? ? C C3 -0.0450(4) 0.1577(1) 0.6230(3) 0.037(1) Uani ? ? C N2 0.0560(3) 0.1079(1) 0.7312(2) 0.036(1) Uani ? ? N C4 0.2688(4) 0.2076(1) 0.5739(3) 0.058(2) Uani ? ? C C5 -0.0135(5) 0.1686(2) 0.3744(3) 0.060(2) Uani ? ? C C6 -0.2535(4) 0.1290(2) 0.5548(3) 0.053(2) Uani ? ? C C7 -0.0654(5) 0.2239(1) 0.6904(3) 0.060(2) Uani ? ? C C8 0.2813(4) 0.0110(1) 0.7540(2) 0.034(1) Uani ? ? C C9 0.4617(4) -0.0101(1) 0.7319(2) 0.040(1) Uani ? ? C C10 0.5712(4) -0.0608(1) 0.8101(3) 0.045(1) Uani ? ? C C11 0.5048(4) -0.0914(1) 0.9112(3) 0.041(1) Uani ? ? C C12 0.3239(4) -0.0722(1) 0.9318(2) 0.034(1) Uani ? ? C C13 0.2122(4) -0.0211(1) 0.8529(2) 0.037(1) Uani ? ? C C14 0.2550(4) -0.1048(1) 1.0425(3) 0.039(1) Uani ? ? C O2 0.3577(3) -0.14324(9) 1.1239(2) 0.056(1) Uani ? ? O O3 0.0700(3) -0.0869(1) 1.0411(2) 0.057(1) Uani ? ? O H01 0.0312 -0.1114 1.1160 0.0690 Uiso ? ? H H1 0.2210 0.2523 0.5589 0.0748 Uiso calc C4 H H2 0.3333 0.2011 0.6689 0.0748 Uiso calc C4 H H3 0.3626 0.1996 0.5233 0.0748 Uiso calc C4 H H4 -0.0675 0.2125 0.3586 0.0836 Uiso calc C5 H H5 0.0810 0.1621 0.3237 0.0836 Uiso calc C5 H H6 -0.1196 0.1369 0.3456 0.0836 Uiso calc C5 H H7 -0.3257 0.1585 0.4846 0.0720 Uiso calc C6 H H8 -0.2403 0.0867 0.5158 0.0720 Uiso calc C6 H H9 -0.3247 0.1239 0.6214 0.0720 Uiso calc C6 H H10 -0.1296 0.2554 0.6218 0.0766 Uiso calc C7 H H11 -0.1446 0.2178 0.7520 0.0766 Uiso calc C7 H H12 0.0644 0.2398 0.7394 0.0766 Uiso calc C7 H H13 0.5089 0.0106 0.6628 0.0515 Uiso calc C9 H H14 0.6937 -0.0751 0.7944 0.0570 Uiso calc C10 H H15 0.5836 -0.1255 0.9665 0.0540 Uiso calc C11 H H16 0.0872 -0.0081 0.8666 0.0465 Uiso calc C13 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 0.038(1) 0.038(1) 0.028(1) -0.000(1) 0.010(1) 0.003(1) C N1 0.053(1) 0.045(1) 0.031(1) 0.009(1) 0.0172(8) 0.0060(9) N O1 0.088(1) 0.070(1) 0.0389(9) 0.028(1) 0.0324(8) 0.0055(9) O C2 0.042(1) 0.043(1) 0.032(1) 0.007(1) 0.010(1) 0.008(1) C C3 0.038(1) 0.036(1) 0.035(1) 0.003(1) 0.009(1) 0.006(1) C N2 0.040(1) 0.037(1) 0.032(1) 0.004(1) 0.0116(8) 0.0058(9) N C4 0.052(2) 0.053(2) 0.071(2) 0.001(1) 0.023(1) 0.016(1) C C5 0.077(2) 0.082(2) 0.034(1) 0.021(2) 0.016(1) 0.021(1) C C6 0.041(2) 0.067(2) 0.054(2) 0.003(1) 0.008(1) 0.011(2) C C7 0.078(2) 0.044(1) 0.064(2) 0.009(1) 0.034(1) 0.005(1) C C8 0.042(1) 0.035(1) 0.027(1) 0.003(1) 0.0104(9) -0.001(1) C C9 0.045(1) 0.042(1) 0.034(1) 0.001(1) 0.014(1) -0.000(1) C C10 0.043(1) 0.048(1) 0.044(1) 0.009(1) 0.016(1) -0.000(1) C C11 0.047(1) 0.040(1) 0.035(1) 0.009(1) 0.008(1) -0.000(1) C C12 0.044(1) 0.031(1) 0.028(1) 0.001(1) 0.009(1) -0.003(1) C C13 0.040(1) 0.035(1) 0.035(1) 0.006(1) 0.0145(9) -0.001(1) C C14 0.053(1) 0.032(1) 0.035(1) 0.005(1) 0.014(1) 0.001(1) C O2 0.066(1) 0.054(1) 0.049(1) 0.0172(9) 0.0220(9) 0.0209(9) O O3 0.060(1) 0.064(1) 0.0476(9) 0.0197(9) 0.0288(7) 0.0231(9) 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 N1 1.403(3) . . ? C1 N2 1.289(3) . . ? C1 C8 1.475(4) . . ? N1 O1 1.265(3) . . ? N1 C2 1.493(3) . . ? C2 C3 1.545(4) . . ? C2 C4 1.526(4) . . ? C2 C5 1.519(4) . . ? C3 N2 1.500(3) . . ? C3 C6 1.521(4) . . ? C3 C7 1.516(4) . . ? C8 C9 1.395(4) . . ? C8 C13 1.388(4) . . ? C9 C10 1.374(4) . . ? C10 C11 1.382(4) . . ? C11 C12 1.382(4) . . ? C12 C13 1.388(4) . . ? C12 C14 1.493(4) . . ? C14 O2 1.201(3) . . ? C14 O3 1.325(3) . . ? C14 H01 1.9068 . . ? O3 H01 1.0047 . . ? 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 111.9(2) . . . ? N1 C1 C8 122.8(2) . . . ? N2 C1 C8 125.2(2) . . . ? C1 N1 O1 126.1(2) . . . ? C1 N1 C2 109.1(2) . . . ? O1 N1 C2 124.7(2) . . . ? N1 C2 C3 98.6(2) . . . ? N1 C2 C4 106.5(2) . . . ? N1 C2 C5 110.2(2) . . . ? C3 C2 C4 113.3(2) . . . ? C3 C2 C5 116.7(2) . . . ? C4 C2 C5 110.5(3) . . . ? C2 C3 N2 103.8(2) . . . ? C2 C3 C6 113.0(2) . . . ? C2 C3 C7 114.9(2) . . . ? N2 C3 C6 105.3(2) . . . ? N2 C3 C7 109.5(2) . . . ? C6 C3 C7 109.6(3) . . . ? C1 N2 C3 108.7(2) . . . ? C1 C8 C9 122.2(2) . . . ? C1 C8 C13 118.5(2) . . . ? C9 C8 C13 119.1(2) . . . ? C8 C9 C10 120.0(2) . . . ? C9 C10 C11 120.7(3) . . . ? C10 C11 C12 119.9(3) . . . ? C11 C12 C13 119.7(2) . . . ? C11 C12 C14 119.4(2) . . . ? C13 C12 C14 120.8(2) . . . ? C8 C13 C12 120.5(2) . . . ? C12 C14 O2 123.1(3) . . . ? C12 C14 O3 112.9(2) . . . ? C12 C14 H01 142.75 . . . ? O2 C14 O3 124.0(3) . . . ? O2 C14 H01 94.13 . . . ? O3 C14 H01 29.87 . . . ? C14 O3 H01 109.06 . . . ? C14 H01 O3 41.07 . . . ? #=============================================================================== data_oNITBAH #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C14H17N2O4' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C14H17N2O4' _chemical_formula_weight 277.30 _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 monoclinic _symmetry_space_group_name_H-M 'C 1 c 1' _symmetry_space_group_name_Hall ' C -2yc' loop_ _symmetry_equiv_pos_as_xyz 'x,y,z' +x,-y,1/2+z 1/2+x,1/2+y,+z 1/2+x,1/2-y,1/2+z _cell_length_a 25.458(2) _cell_length_b 7.6775(6) _cell_length_c 15.1702(5) _cell_angle_alpha 90 _cell_angle_beta 107.158(4) _cell_angle_gamma 90 _cell_volume 2833.2(6) _cell_formula_units_z 8 _cell_measurement_temperature 294 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 18.4 _cell_measurement_theta_max 20.5 _cell_special_details ; ? ; _exptl_crystal_description prism _exptl_crystal_colour 'dark green' _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.30 _exptl_crystal_density_method 'none' _exptl_crystal_F_000 1176 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type psi_scans_(North,_Phillips,_Mathews,_1968) _exptl_absorpt_correction_T_min 0.9471 _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_radiation_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 11 -1 2 -3 -3 5 1 -3 -5 _diffrn_reflns_number 3215 _diffrn_reflns_av_R_equivalents 0.013 _diffrn_reflns_av_sigmaI/netI 0.333 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.5 _diffrn_reflns_theta_max 26.28 _reflns_number_total 3098 _reflns_number_gt 2158 _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_MolEN_(Fair,_1990)' _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^) + 0.0049 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 0(1) _refine_ls_number_reflns 2158 _refine_ls_number_parameters 359 _refine_ls_number_restraints 2 _refine_ls_number_constraints 0 _refine_ls_abs_structure_details ; ? ; _refine_ls_R_factor_all 0.064 _refine_ls_R_factor_gt 0.035 _refine_ls_wR_factor_all 0.063 _refine_ls_wR_factor_ref 0.046 _refine_ls_goodness_of_fit_all 1.395 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_shift/su_max 0.002 _refine_ls_shift/esd_mean 0.000 _refine_diff_density_max 0.211 _refine_diff_density_min -0.194 #=============================================================================== # 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 0.2639 0.1361(3) 0.6089 0.030(1) Uij ? ? C N1 0.27160(9) 0.1573(3) 0.5274(1) 0.0301(9) Uij ? ? N O1 0.28724(8) 0.3014(3) 0.4978(1) 0.0397(9) Uij ? ? O C2 0.2529(1) 0.0038(4) 0.4649(2) 0.036(1) Uij ? ? C C3 0.2502(1) -0.1396(4) 0.5367(2) 0.038(1) Uij ? ? C N2 0.24621(9) -0.0273(3) 0.6158(1) 0.036(1) Uij ? ? N O2 0.2335(1) -0.0884(3) 0.6848(1) 0.056(1) Uij ? ? O C4 0.2937(2) -0.0310(5) 0.4116(2) 0.062(2) Uij ? ? C C5 0.1970(2) 0.0544(5) 0.3992(2) 0.055(2) Uij ? ? C C6 0.3033(2) -0.2423(5) 0.5724(3) 0.061(2) Uij ? ? C C7 0.2010(2) -0.2591(5) 0.5077(3) 0.063(2) Uij ? ? C C8 0.2780(1) 0.2662(3) 0.6834(2) 0.032(1) Uij ? ? C C9 0.2386(1) 0.3618(4) 0.7104(2) 0.037(1) Uij ? ? C C10 0.2560(1) 0.4839(4) 0.7807(2) 0.049(1) Uij ? ? C C11 0.3110(2) 0.5106(5) 0.8229(2) 0.053(2) Uij ? ? C C12 0.3497(1) 0.4128(5) 0.7983(2) 0.048(2) Uij ? ? C C13 0.3334(1) 0.2915(4) 0.7285(2) 0.041(1) Uij ? ? C C14 0.1788(1) 0.3335(4) 0.6627(2) 0.043(1) Uij ? ? C O3 0.16108(8) 0.2701(3) 0.5878(2) 0.050(1) Uij ? ? O O4 0.1473(1) 0.3851(4) 0.7134(2) 0.077(1) Uij ? ? O C15 0.5141(1) 0.1083(4) 0.7247(2) 0.032(1) Uij ? ? C N3 0.52397(9) -0.0596(3) 0.7173(2) 0.033(1) Uij ? ? N O5 0.54122(9) -0.1285(3) 0.6527(1) 0.049(1) Uij ? ? O C16 0.5051(1) -0.1698(4) 0.7835(2) 0.040(1) Uij ? ? C C17 0.4999(1) -0.0298(4) 0.8546(2) 0.049(2) Uij ? ? C N4 0.4959(1) 0.1331(3) 0.7985(2) 0.044(1) Uij ? ? N O6 0.4813(1) 0.2795(3) 0.8234(2) 0.069(1) Uij ? ? O C18 0.5461(2) -0.3138(5) 0.8202(3) 0.062(2) Uij ? ? C C19 0.4504(2) -0.2469(6) 0.7270(3) 0.071(2) Uij ? ? C C20 0.5516(3) -0.0120(6) 0.9360(3) 0.072(3) Uij ? ? C C21 0.4500(2) -0.0461(6) 0.8884(3) 0.104(2) Uij ? ? C C22 0.5255(1) 0.2458(4) 0.6659(2) 0.035(1) Uij ? ? C C23 0.4833(1) 0.3339(4) 0.6006(2) 0.037(1) Uij ? ? C C24 0.4969(1) 0.4657(4) 0.5489(2) 0.045(1) Uij ? ? C C25 0.5517(1) 0.5089(4) 0.5606(2) 0.054(1) Uij ? ? C C26 0.5925(1) 0.4228(5) 0.6245(2) 0.055(2) Uij ? ? C C27 0.5797(1) 0.2914(4) 0.6771(2) 0.048(2) Uij ? ? C C28 0.4252(1) 0.2791(4) 0.5849(2) 0.036(1) Uij ? ? C O7 0.3892(1) 0.3991(3) 0.5439(2) 0.056(1) Uij ? ? O O8 0.41208(8) 0.1379(3) 0.6063(1) 0.044(1) Uij ? ? O H1 0.2818 -0.1283 0.3721 0.0765 Uiso calc C4 H H2 0.2961 0.0685 0.3758 0.0765 Uiso calc C4 H H3 0.3288 -0.0551 0.4537 0.0765 Uiso calc C4 H H4 0.1831 -0.0389 0.3578 0.0793 Uiso calc C5 H H5 0.1722 0.0785 0.4337 0.0793 Uiso calc C5 H H6 0.2009 0.1551 0.3653 0.0793 Uiso calc C5 H H7 0.2992 -0.3271 0.6155 0.0809 Uiso calc C6 H H8 0.3115 -0.2988 0.5222 0.0809 Uiso calc C6 H H9 0.3325 -0.1653 0.6016 0.0809 Uiso calc C6 H H10 0.2028 -0.3415 0.5552 0.0843 Uiso calc C7 H H11 0.1683 -0.1925 0.4968 0.0843 Uiso calc C7 H H12 0.2011 -0.3186 0.4528 0.0843 Uiso calc C7 H H13 0.2296 0.5493 0.7998 0.0606 Uiso calc C10 H H14 0.3224 0.5972 0.8693 0.0691 Uiso calc C11 H H15 0.3877 0.4288 0.8295 0.0643 Uiso calc C12 H H16 0.3602 0.2250 0.7111 0.0536 Uiso calc C13 H H17 0.5461 -0.3918 0.7716 0.0829 Uiso calc C18 H H18 0.5818 -0.2652 0.8447 0.0829 Uiso calc C18 H H19 0.5362 -0.3750 0.8674 0.0829 Uiso calc C18 H H20 0.4361 -0.3189 0.7654 0.0931 Uiso calc C19 H H21 0.4252 -0.1555 0.7025 0.0931 Uiso calc C19 H H22 0.4558 -0.3144 0.6779 0.0931 Uiso calc C19 H H23 0.5559 -0.1129 0.9737 0.1141 Uiso calc C20 H H24 0.5827 0.0002 0.9139 0.1141 Uiso calc C20 H H25 0.5486 0.0879 0.9711 0.1141 Uiso calc C20 H H26 0.4528 -0.1495 0.9239 0.1216 Uiso calc C21 H H27 0.4480 0.0518 0.9255 0.1216 Uiso calc C21 H H28 0.4178 -0.0510 0.8370 0.1216 Uiso calc C21 H H29 0.4686 0.5273 0.5051 0.0583 Uiso calc C24 H H30 0.5606 0.5982 0.5241 0.0664 Uiso calc C25 H H31 0.6298 0.4532 0.6329 0.0701 Uiso calc C26 H H32 0.6084 0.2319 0.7212 0.0624 Uiso calc C27 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 0.027(1) 0.032(1) 0.033(1) 0.001(1) 0.0106(8) -0.001(1) C N1 0.0323(9) 0.032(1) 0.0261(9) -0.0011(9) 0.0096(7) -0.0002(9) N O1 0.0427(9) 0.040(1) 0.0365(8) -0.0050(9) 0.0132(7) 0.0096(8) O C2 0.037(1) 0.045(2) 0.028(1) -0.005(1) 0.0072(9) -0.005(1) C C3 0.046(1) 0.032(1) 0.037(1) -0.002(1) 0.011(1) -0.008(1) C N2 0.042(1) 0.034(1) 0.033(1) -0.004(1) 0.0139(8) -0.0002(9) N O2 0.072(1) 0.056(1) 0.0429(9) -0.014(1) 0.0291(7) 0.006(1) O C4 0.074(2) 0.066(2) 0.048(1) -0.009(2) 0.036(1) -0.018(1) C C5 0.055(2) 0.071(2) 0.042(2) -0.006(2) -0.008(2) -0.000(2) C C6 0.072(2) 0.049(2) 0.065(2) 0.022(2) 0.018(2) 0.002(2) C C7 0.077(2) 0.054(2) 0.061(2) -0.027(2) 0.016(2) -0.007(2) C C8 0.037(1) 0.033(1) 0.026(1) -0.005(1) 0.0116(8) -0.001(1) C C9 0.041(1) 0.034(1) 0.036(1) 0.003(1) 0.016(1) 0.001(1) C C10 0.061(1) 0.042(2) 0.045(1) 0.003(1) 0.028(1) -0.009(1) C C11 0.070(2) 0.047(2) 0.044(1) -0.011(2) 0.020(1) -0.017(1) C C12 0.045(1) 0.063(2) 0.038(1) -0.013(1) 0.009(1) -0.009(1) C C13 0.037(1) 0.052(2) 0.036(1) -0.001(1) 0.0138(9) -0.005(1) C C14 0.044(1) 0.038(1) 0.049(1) 0.006(1) 0.022(1) 0.001(1) C O3 0.0364(9) 0.067(1) 0.051(1) -0.001(1) 0.0150(7) -0.008(1) O O4 0.051(1) 0.113(2) 0.078(1) 0.007(1) 0.0325(9) -0.033(1) O C15 0.028(1) 0.036(1) 0.033(1) 0.002(1) 0.0082(9) 0.001(1) C N3 0.033(1) 0.033(1) 0.0339(9) 0.003(1) 0.0102(8) -0.001(1) N O5 0.0513(9) 0.049(1) 0.0482(9) 0.0043(9) 0.0253(7) -0.0099(9) O C16 0.045(1) 0.036(1) 0.040(1) 0.004(1) 0.014(1) 0.004(1) C C17 0.068(2) 0.041(1) 0.042(1) 0.014(1) 0.025(1) 0.010(1) C N4 0.054(1) 0.037(1) 0.041(1) 0.010(1) 0.0211(9) 0.001(1) N O6 0.106(1) 0.042(1) 0.073(1) 0.019(1) 0.0549(9) 0.001(1) O C18 0.084(2) 0.043(2) 0.065(2) 0.020(2) 0.023(2) 0.008(2) C C19 0.062(2) 0.070(2) 0.082(2) -0.025(2) 0.020(2) 0.003(2) C C20 0.136(4) 0.067(2) 0.040(2) 0.013(3) -0.004(2) -0.007(2) C C21 0.134(2) 0.078(3) 0.109(2) 0.029(2) 0.097(1) 0.030(2) C C22 0.038(1) 0.031(1) 0.038(1) -0.002(1) 0.0153(9) -0.004(1) C C23 0.039(1) 0.036(1) 0.036(1) -0.005(1) 0.0144(9) -0.004(1) C C24 0.055(2) 0.035(1) 0.047(1) -0.004(1) 0.019(1) 0.003(1) C C25 0.063(1) 0.039(2) 0.063(1) -0.013(1) 0.037(1) -0.006(1) C C26 0.047(1) 0.046(2) 0.079(2) -0.008(1) 0.035(1) -0.009(2) C C27 0.039(1) 0.046(2) 0.061(2) -0.001(1) 0.019(1) -0.001(2) C C28 0.038(1) 0.038(1) 0.032(1) -0.001(1) 0.0106(9) 0.003(1) C O7 0.042(1) 0.051(1) 0.083(1) -0.001(1) 0.003(1) 0.029(1) O O8 0.0389(9) 0.038(1) 0.056(1) -0.0027(9) 0.0157(8) 0.0085(9) 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 N1 1.317(4) . . ? C1 N2 1.347(4) . . ? C1 C8 1.472(4) . . ? N1 O1 1.300(3) . . ? N1 C2 1.499(4) . . ? C2 C3 1.566(5) . . ? C2 C4 1.516(5) . . ? C2 C5 1.527(5) . . ? C3 N2 1.505(4) . . ? C3 C6 1.521(5) . . ? C3 C7 1.508(5) . . ? N2 O2 1.274(3) . . ? C8 C9 1.399(4) . . ? C8 C13 1.387(5) . . ? C9 C10 1.391(5) . . ? C9 C14 1.495(5) . . ? C10 C11 1.373(6) . . ? C11 C12 1.375(6) . . ? C12 C13 1.380(5) . . ? C14 O3 1.195(4) . . ? C14 O4 1.325(4) . . ? C15 N3 1.325(4) . . ? C15 N4 1.346(4) . . ? C15 C22 1.465(4) . . ? N3 O5 1.299(3) . . ? N3 C16 1.497(4) . . ? C16 C17 1.555(5) . . ? C16 C18 1.509(5) . . ? C16 C19 1.524(6) . . ? C17 N4 1.499(4) . . ? C17 C20 1.522(6) . . ? C17 C21 1.510(6) . . ? N4 O6 1.276(4) . . ? C22 C23 1.401(5) . . ? C22 C27 1.385(5) . . ? C23 C24 1.385(5) . . ? C23 C28 1.488(4) . . ? C24 C25 1.391(5) . . ? C25 C26 1.365(6) . . ? C26 C27 1.383(5) . . ? C28 O7 1.319(4) . . ? C28 O8 1.207(4) . . ? 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 109.5(2) . . . ? N1 C1 C8 124.6(3) . . . ? N2 C1 C8 125.7(3) . . . ? C1 N1 O1 125.1(2) . . . ? C1 N1 C2 112.9(2) . . . ? O1 N1 C2 121.6(2) . . . ? N1 C2 C3 100.6(2) . . . ? N1 C2 C4 109.6(3) . . . ? N1 C2 C5 105.9(3) . . . ? C3 C2 C4 115.1(3) . . . ? C3 C2 C5 114.2(3) . . . ? C4 C2 C5 110.6(3) . . . ? C2 C3 N2 100.3(2) . . . ? C2 C3 C6 113.3(3) . . . ? C2 C3 C7 115.3(3) . . . ? N2 C3 C6 106.0(3) . . . ? N2 C3 C7 109.6(3) . . . ? C6 C3 C7 111.3(3) . . . ? C1 N2 C3 111.6(2) . . . ? C1 N2 O2 125.4(3) . . . ? C3 N2 O2 122.5(3) . . . ? C1 C8 C9 123.2(3) . . . ? C1 C8 C13 117.1(3) . . . ? C9 C8 C13 119.6(3) . . . ? C8 C9 C10 119.0(3) . . . ? C8 C9 C14 119.9(3) . . . ? C10 C9 C14 121.1(3) . . . ? C9 C10 C11 120.5(3) . . . ? C10 C11 C12 120.5(3) . . . ? C11 C12 C13 119.9(3) . . . ? C8 C13 C12 120.4(3) . . . ? C9 C14 O3 124.3(3) . . . ? C9 C14 O4 112.3(3) . . . ? O3 C14 O4 123.4(3) . . . ? N3 C15 N4 109.2(3) . . . ? N3 C15 C22 125.0(3) . . . ? N4 C15 C22 125.6(3) . . . ? C15 N3 O5 125.1(3) . . . ? C15 N3 C16 112.8(2) . . . ? O5 N3 C16 121.6(2) . . . ? N3 C16 C17 100.6(2) . . . ? N3 C16 C18 109.8(3) . . . ? N3 C16 C19 105.2(3) . . . ? C17 C16 C18 116.2(3) . . . ? C17 C16 C19 114.1(3) . . . ? C18 C16 C19 109.9(3) . . . ? C16 C17 N4 100.9(2) . . . ? C16 C17 C20 113.2(3) . . . ? C16 C17 C21 115.5(4) . . . ? N4 C17 C20 106.5(3) . . . ? N4 C17 C21 109.8(3) . . . ? C20 C17 C21 110.2(4) . . . ? C15 N4 C17 111.8(3) . . . ? C15 N4 O6 125.0(3) . . . ? C17 N4 O6 123.0(3) . . . ? C15 C22 C23 122.1(3) . . . ? C15 C22 C27 118.5(3) . . . ? C23 C22 C27 119.5(3) . . . ? C22 C23 C24 119.1(3) . . . ? C22 C23 C28 119.6(3) . . . ? C24 C23 C28 121.3(3) . . . ? C23 C24 C25 120.7(3) . . . ? C24 C25 C26 119.9(3) . . . ? C25 C26 C27 120.2(3) . . . ? C22 C27 C26 120.7(3) . . . ? C23 C28 O7 113.4(3) . . . ? C23 C28 O8 123.5(3) . . . ? O7 C28 O8 123.0(3) . . . ?