# # 5-azaindol-2-yl nitronyl nitroxide # ############################################################################## data_5-NIn-NN _audit_creation_date 'Mon Dec 17 19:16:07 2001' _audit_creation_method 'by teXsan' _audit_update_record ? #------------------------------------------------------------------------------ _publ_contact_author_name ' Prof. Naoki Yoshioka' _publ_contact_author_address ; Department of Applied Chemistry Faculty of Science and Technology Keio University 3-14-1 Hiyoshi Kohoku-ku Yokohama 223-8522 Japan ; _publ_contact_author_email ' yoshioka@applc.keio.ac.jp ' _publ_contact_author_fax ' (81)45 566 1551 ' _publ_contact_author_phone ' (81)45 566 1585 ' #--------------------------------------------------------------------------------- # Data items needed for Supporting Information #--------------------------------------------------------------------------------- _publ_contact_letter ; This CIF is aimed for Supporting Information. The original paper has be submitted. Journal:Crystal Growth & Design Title:Metamagnetic behavior observed in purely organic 5-azaindol-2-yl nitronyl nitroxide brick-wall architecture Author: Hideaki Nagashima, Shin'ya Fujita, Hidenari Inoue, Naoki Yoshioka ; # TITLE _publ_section_title ; Supporting information of X-ray crystal analysis of 5-azaindole nitronyl nitroxide ; _publ_section_references ; Molecular Structure Corporation, Rigaku Corporation. (2000). teXsan. Single Crystal Structure Analysis Software. Version 1.11. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. Rigaku, 3-9-12 Akishima, Tokyo, Japan. North, A.C.T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359. ; #------------------------------------------------------------------------------ data_5NIn-NN #------------------------------------------------------------------------------ # CHEMICAL DATA _chemical_formula_sum 'C14 H17 N4 O2 ' _chemical_formula_moiety 'C14 H17 N4 O2 ' _chemical_formula_weight 273.31 _chemical_melting_point 469-479 #------------------------------------------------------------------------------ # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/a 1' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz x,y,z 1/2-x,1/2+y,-z -x,-y,-z 1/2+x,1/2-y,z _cell_length_a 13.537(3) _cell_length_b 9.918(1) _cell_length_c 11.304(2) _cell_angle_alpha 90 _cell_angle_beta 109.31(1) _cell_angle_gamma 90 _cell_volume 1432.2(5) _cell_formula_units_Z 4 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10.1 _cell_measurement_theta_max 12.9 _cell_measurement_temperature 297.2 #------------------------------------------------------------------------------ _exptl_crystal_description 'needle' _exptl_crystal_colour 'dark-blue' _exptl_crystal_size_max 0.7 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.2 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.267 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North, Phillips & Mathews, 1968)' _exptl_absorpt_correction_T_min 0.959 _exptl_absorpt_correction_T_max 0.983 #------------------------------------------------------------------------------ # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_device_type 'Rigaku AFC7R' _diffrn_measurement_method \q-2\q _diffrn_reflns_number 3634 _diffrn_reflns_av_R_equivalents 0.0248 _diffrn_reflns_theta_min 2.5 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% 0 #------------------------------------------------------------------------------ # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > 0.0 sigma(F^2^). The weighted R-factor (wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 3291 _reflns_number_gt 2230 _reflns_threshold_expression >2.0sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.045 _refine_ls_wR_factor_ref 0.141 _refine_ls_hydrogen_treatment refall _refine_ls_number_reflns 3291 _refine_ls_number_parameters 248 _refine_ls_goodness_of_fit_ref 1.00 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^) + (0.0752P)^2^+0.1732P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max 0.001 _refine_ls_extinction_method none _refine_diff_density_max 0.15 _refine_diff_density_min -0.23 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.003 0.002 ;International Tables for Crystallography (1992, Vol. C) ; 'H' 'H' 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C) ; 'N' 'N' 0.006 0.003 ;International Tables for Crystallography (1992, Vol. C) ; 'O' 'O' 0.011 0.006 ;International Tables for Crystallography (1992, Vol. C) ; #------------------------------------------------------------------------------ # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.76637(9) 0.1818(2) 0.8930(1) 0.06(3) Uani 1.00 d . . . O2 O 1.0514(1) 0.1482(2) 0.7593(2) 0.0825(6) Uani 1.00 d . . . N3 N 0.8228(1) 0.1527(1) 0.8255(1) 0.0405(3) Uani 1.00 d . . . N4 N 0.9589(1) 0.1342(2) 0.7634(1) 0.05(3) Uani 1.00 d . . . N5 N 1.0856(1) 0.3036(1) 0.9711(1) 0.0404(3) Uani 1.00 d . . . N6 N 1.1613(1) 0.5136(2) 1.3029(1) 0.0574(4) Uani 1.00 d . . . C7 C 0.9242(1) 0.1847(2) 0.8532(1) 0.04(3) Uani 1.00 d . . . C8 C 0.7839(1) 0.0611(2) 0.7142(2) 0.0447(4) Uani 1.00 d . . . C9 C 0.8734(1) 0.0737(2) 0.6563(2) 0.0470(4) Uani 1.00 d . . . C10 C 0.6769(2) 0.1098(3) 0.6305(2) 0.07(5) Uani 1.00 d . . . C11 C 0.7756(3) -0.0784(2) 0.7671(3) 0.0771(7) Uani 1.00 d . . . C12 C 0.8518(2) 0.1766(2) 0.5498(2) 0.0653(5) Uani 1.00 d . . . C13 C 0.9107(2) -0.0582(3) 0.6179(3) 0.07(5) Uani 1.00 d . . . C14 C 0.9853(1) 0.2614(2) 0.9595(1) 0.0380(3) Uani 1.00 d . . . C15 C 0.9593(1) 0.3076(2) 1.0601(2) 0.0435(4) Uani 1.00 d . . . C16 C 1.1242(1) 0.3772(2) 1.0783(1) 0.04(3) Uani 1.00 d . . . C17 C 1.0472(1) 0.3815(2) 1.1367(1) 0.0411(4) Uani 1.00 d . . . C18 C 1.0710(1) 0.4521(2) 1.2498(2) 0.0538(4) Uani 1.00 d . . . C19 C 1.2330(2) 0.5074(2) 1.2430(2) 0.05(3) Uani 1.00 d . . . C20 C 1.2199(1) 0.4418(2) 1.1322(2) 0.0465(4) Uani 1.00 d . . . H5 H 1.121(2) 0.285(2) 0.921(2) 0.06480(8) Uiso 1.00 d . . . H10A H 0.626(2) 0.109(3) 0.678(2) 0.0936(1) Uiso 1.00 d . . . H10B H 0.654(2) 0.056(3) 0.554(3) 0.0969(1) Uiso 1.00 d . . . H10C H 0.687(2) 0.210(3) 0.607(2) 0.0874(1) Uiso 1.00 d . . . H11A H 0.726(2) -0.069(3) 0.813(3) 0.0982(1) Uiso 1.00 d . . . H11B H 0.845(3) -0.112(3) 0.823(3) 0.1194(1) Uiso 1.00 d . . . H11C H 0.744(2) -0.143(3) 0.690(3) 0.1028(1) Uiso 1.00 d . . . H12A H 0.829(2) 0.271(3) 0.573(2) 0.08599(9) Uiso 1.00 d . . . H12B H 0.793(2) 0.142(3) 0.477(2) 0.08561(9) Uiso 1.00 d . . . H12C H 0.914(2) 0.184(3) 0.528(2) 0.08414(10) Uiso 1.00 d . . . H13A H 0.931(2) -0.117(3) 0.697(3) 0.0870(1) Uiso 1.00 d . . . H13B H 0.973(2) -0.038(3) 0.592(2) 0.0927(1) Uiso 1.00 d . . . H13C H 0.857(2) -0.103(3) 0.556(3) 0.1009(1) Uiso 1.00 d . . . H15 H 0.894(1) 0.290(2) 1.071(2) 0.05154(6) Uiso 1.00 d . . . H18 H 1.019(2) 0.457(2) 1.292(2) 0.05829(7) Uiso 1.00 d . . . H19 H 1.298(2) 0.556(2) 1.284(2) 0.06377(7) Uiso 1.00 d . . . H20 H 1.272(2) 0.439(2) 1.097(2) 0.06502(7) Uiso 1.00 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.0376(6) 0.097(1) 0.0531(7) -0.0050(6) 0.0259(5) -0.0088(7) O2 0.0446(7) 0.132(1) 0.084(1) -0.0189(8) 0.0388(7) -0.0475(10) N3 0.0334(6) 0.0518(7) 0.0389(6) -0.0010(5) 0.0157(5) 0.0011(6) N4 0.0379(7) 0.0622(9) 0.0493(8) -0.0031(6) 0.0215(6) -0.0131(7) N5 0.0339(6) 0.0522(8) 0.0385(7) -0.0009(5) 0.0165(5) -0.0032(6) N6 0.0584(9) 0.0635(10) 0.0460(8) 0.0014(7) 0.0113(7) -0.0116(7) C7 0.0340(7) 0.0433(8) 0.0384(7) 0.0020(6) 0.0147(6) 0.0009(6) C8 0.0408(8) 0.0467(9) 0.0465(8) -0.0062(7) 0.0141(7) -0.0026(7) C9 0.0488(9) 0.0483(9) 0.0466(9) -0.0055(7) 0.0196(7) -0.0088(7) C10 0.046(1) 0.104(2) 0.055(1) 0.001(1) 0.0063(9) -0.012(1) C11 0.094(2) 0.055(1) 0.095(2) -0.018(1) 0.048(2) 0.002(1) C12 0.082(2) 0.070(1) 0.048(1) -0.013(1) 0.027(1) -0.0023(10) C13 0.082(2) 0.063(1) 0.087(2) -0.001(1) 0.041(1) -0.025(1) C14 0.0323(7) 0.0461(8) 0.0375(7) 0.0027(6) 0.0139(6) 0.0022(6) C15 0.0351(8) 0.0573(10) 0.0421(8) 0.0028(7) 0.0181(7) -0.0016(7) C16 0.0373(8) 0.0408(8) 0.0364(7) 0.0040(6) 0.0115(6) 0.0042(6) C17 0.0389(8) 0.0467(9) 0.0384(8) 0.0065(6) 0.0138(6) 0.0016(7) C18 0.0505(10) 0.068(1) 0.0448(9) 0.0059(9) 0.0186(8) -0.0076(8) C19 0.0509(10) 0.0529(10) 0.0489(9) -0.0057(8) 0.0083(8) -0.0016(8) C20 0.0399(8) 0.0539(10) 0.0450(9) -0.0034(7) 0.0129(7) 0.0022(7) #------------------------------------------------------------------------------ _computing_data_collection 'WinAFC' _computing_cell_refinement 'WinAFC' _computing_data_reduction 'teXsan Ver. 1.11' _computing_structure_solution SIR92 _computing_structure_refinement 'SHELXL97' _computing_publication_material 'teXsan Ver. 1.11' _computing_molecular_graphics ORTEP #------------------------------------------------------------------------------ _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 N3 1.278(2) . . yes O2 N4 1.275(2) . . yes N3 C7 1.341(2) . . yes N3 C8 1.499(2) . . yes N4 C7 1.349(2) . . yes N4 C9 1.496(2) . . yes N5 C14 1.385(2) . . yes N5 C16 1.361(2) . . yes N5 H5 0.88(3) . . no N6 C18 1.320(2) . . yes N6 C19 1.356(3) . . yes C7 C14 1.431(2) . . yes C8 C9 1.561(3) . . yes C8 C10 1.522(3) . . yes C8 C11 1.526(3) . . yes C9 C12 1.531(3) . . yes C9 C13 1.517(3) . . yes C10 H10A 1.00(3) . . no C10 H10B 0.98(3) . . no C10 H10C 1.05(3) . . no C11 H11A 0.97(4) . . no C11 H11B 1.00(3) . . no C11 H11C 1.05(3) . . no C12 H12A 1.05(3) . . no C12 H12B 1.00(2) . . no C12 H12C 0.96(3) . . no C13 H13A 1.03(3) . . no C13 H13B 1.01(3) . . no C13 H13C 0.94(3) . . no C14 C15 1.375(3) . . yes C15 C17 1.422(2) . . yes C15 H15 0.94(2) . . no C16 C17 1.408(3) . . yes C16 C20 1.391(2) . . yes C17 C18 1.399(3) . . yes C18 H18 0.98(2) . . no C19 C20 1.369(3) . . yes C19 H19 0.98(2) . . no C20 H20 0.93(3) . . 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 O1 N3 C7 125.1(1) . . . yes O1 N3 C8 121.6(1) . . . yes C7 N3 C8 112.8(1) . . . yes O2 N4 C7 125.3(1) . . . yes O2 N4 C9 121.4(2) . . . yes C7 N4 C9 112.9(1) . . . yes C14 N5 C16 108.8(1) . . . yes C14 N5 H5 127(1) . . . no C16 N5 H5 124(1) . . . no C18 N6 C19 117.4(2) . . . yes N3 C7 N4 108.7(1) . . . yes N3 C7 C14 125.8(2) . . . yes N4 C7 C14 125.5(1) . . . yes N3 C8 C9 101.4(1) . . . yes N3 C8 C10 109.1(2) . . . yes N3 C8 C11 105.7(2) . . . yes C9 C8 C10 115.1(2) . . . yes C9 C8 C11 113.9(2) . . . yes C10 C8 C11 110.7(2) . . . yes N4 C9 C8 101.2(1) . . . yes N4 C9 C12 105.3(1) . . . yes N4 C9 C13 109.6(2) . . . yes C8 C9 C12 114.2(2) . . . yes C8 C9 C13 115.4(2) . . . yes C12 C9 C13 110.2(2) . . . yes C8 C10 H10A 110(1) . . . no C8 C10 H10B 110(2) . . . no C8 C10 H10C 107(1) . . . no H10A C10 H10B 114(2) . . . no H10A C10 H10C 108(2) . . . no H10B C10 H10C 109(2) . . . no C8 C11 H11A 106(2) . . . no C8 C11 H11B 112(2) . . . no C8 C11 H11C 107(2) . . . no H11A C11 H11B 111(3) . . . no H11A C11 H11C 109(2) . . . no H11B C11 H11C 112(2) . . . no C9 C12 H12A 113(1) . . . no C9 C12 H12B 108(2) . . . no C9 C12 H12C 108(1) . . . no H12A C12 H12B 107(2) . . . no H12A C12 H12C 111(2) . . . no H12B C12 H12C 110(2) . . . no C9 C13 H13A 105(2) . . . no C9 C13 H13B 108(2) . . . no C9 C13 H13C 112(2) . . . no H13A C13 H13B 111(2) . . . no H13A C13 H13C 107(2) . . . no H13B C13 H13C 113(3) . . . no N5 C14 C7 121.1(1) . . . yes N5 C14 C15 109.4(1) . . . yes C7 C14 C15 129.5(1) . . . yes C14 C15 C17 106.5(2) . . . yes C14 C15 H15 123(1) . . . no C17 C15 H15 130(1) . . . no N5 C16 C17 107.9(1) . . . yes N5 C16 C20 131.7(2) . . . yes C17 C16 C20 120.4(1) . . . yes C15 C17 C16 107.4(1) . . . yes C15 C17 C18 135.1(2) . . . yes C16 C17 C18 117.5(1) . . . yes N6 C18 C17 123.1(2) . . . yes N6 C18 H18 118(1) . . . no C17 C18 H18 119(1) . . . no N6 C19 C20 125.5(2) . . . yes N6 C19 H19 115(1) . . . no C20 C19 H19 120(1) . . . no C16 C20 C19 116.1(2) . . . yes C16 C20 H20 122(1) . . . no C19 C20 H20 122(1) . . . no #------------------------------------------------------------------------------ loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N5 H5 O2 0.88(3) 2.22(2) 2.755(2) 119(2) 1_555 N5 H5 O1 0.88(3) 2.12(2) 2.867(2) 143(2) 4_555