Supplementary Material (ESI) for Perkin Transactions This journal is © The Royal Society of Chemistry 2001 data__C20H15NO2_ _database_code_CSD 163573 _journal_coden_Cambridge 207 _publ_requested_journal 'Perkin Transactions 1' loop_ _publ_author_name 'Kikugawa, Yasuo' 'Nara, Shigeru' 'Ohwada, Atsushi' 'Sakamoto, Takeshi' _audit_creation_date '2001-08-27' _audit_creation_method 'by CrystalStructure v2.00' _audit_update_record ? #============================================================================== # SUBMISSION DETAILS _publ_contact_author_name 'Prof Yasuo Kikugawa' _publ_contact_author_email 'kikugawa@josai.ac.jp' _publ_contact_author_address ; Faculty of Pharmaceutical Sciences Josai University 1-1 Keyakidai Sakado Saitama 350-0295 Japan ; _publ_requested_journal 'Perkin Trans 1' _publ_requested_category 'CHOOSE FI FM FO CI CM CO or AD' _publ_requested_coeditor_name ? #============================================================================== # TITLE AND AUTHOR LIST _publ_section_title ; Reaction of Phenylhydrazines with Arenes in the Presence of Aluminium Trichloride ; _publ_section_references ; ENTER OTHER REFERENCES Molecular Structure Corporation and Rigaku Corporation. (2001). CrystalStructure. Single Crystal Structure Analysis Software. Version 2.00. MSC, 9009 New Trails Drive, The Woodlands, TX, USA 77381-5209. Rigaku, 3-9-12 Akishima, Tokyo 196-8666, Japan. Watkin, D.J., Prout, C.K. Carruthers, J.R. & Betteridge, P.W., CRYSTALS Issue 10, Chemical Crystallography Laboratory, Oxford, UK. Larson, A. C. (1970), Crystallographic Computing, 291-294. ed F. R. Ahmed, Munksgaard, Copenhagen. ; #============================================================================== #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C20 H15 N O2 ' _chemical_formula_moiety 'C20 H15 N O2 ' _chemical_formula_weight 301.34 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x,y,z' '-x,-y,-z' '-x,y+1/2,-z+1/2' 'x,-y+1/2,z+1/2' #------------------------------------------------------------------------------ _cell_length_a 12.9873(3) _cell_length_b 6.7803(2) _cell_length_c 17.2761(4) _cell_angle_alpha 90 _cell_angle_beta 96.1490(5) _cell_angle_gamma 90 _cell_volume 1512.54(6) _cell_formula_units_Z 4 _cell_measurement_reflns_used 12904 _cell_measurement_theta_min 3.2 _cell_measurement_theta_max 27.5 _cell_measurement_temperature 296.1 #------------------------------------------------------------------------------ _exptl_crystal_description 'chunk' _exptl_crystal_colour 'yellow' _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.45 _exptl_crystal_density_diffrn 1.323 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _exptl_absorpt_correction_T_min 0.831 _exptl_absorpt_correction_T_max 0.962 #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_reflns_number 6103 _diffrn_reflns_av_R_equivalents 0.013 _diffrn_reflns_theta_max 27.48 _diffrn_measured_fraction_theta_max 0.9995 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.9995 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > 2.0 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 3761 _reflns_number_gt 2547 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.0420 _refine_ls_wR_factor_ref 0.0710 _refine_ls_hydrogen_treatment refall _refine_ls_number_reflns 2559 _refine_ls_number_parameters 224 _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[0.003Fo^2^ + 1.000\s^2^(Fo)]' _refine_ls_shift/su_max 0.0000 _refine_diff_density_max 0.27 _refine_diff_density_min -0.22 _refine_ls_extinction_method 'Larson (1970) Crystallographic Computing eq. 22' _refine_ls_extinction_coef 310.1(6) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.006 0.003 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; 'H' 'H' 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; 'N' 'N' 0.011 0.006 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; 'O' 'O' 0.017 0.010 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.6800(1) 0.4975(2) 0.75387(6) 0.0519(3) Uani 1.00 1 d . . . O2 O 0.6977(1) 0.7110(2) 1.01942(8) 0.0601(4) Uani 1.00 1 d . . . N1 N 0.8054(1) 0.4462(2) 1.02978(7) 0.0429(4) Uani 1.00 1 d . . . C1 C 0.6823(1) 0.0865(2) 0.88521(9) 0.0425(4) Uani 1.00 1 d . . . C2 C 0.7274(1) 0.1691(2) 0.95384(9) 0.0418(4) Uani 1.00 1 d . . . C3 C 0.7601(1) 0.3663(2) 0.95662(9) 0.0399(4) Uani 1.00 1 d . . . C4 C 0.7493(1) 0.4835(3) 0.89055(9) 0.0454(4) Uani 1.00 1 d . . . C5 C 0.5898(1) 0.4015(4) 0.6276(1) 0.0600(6) Uani 1.00 1 d . . . C6 C 0.5406(2) 0.2475(4) 0.5867(1) 0.0674(6) Uani 1.00 1 d . . . C7 C 0.5321(2) 0.0633(4) 0.6198(1) 0.0684(6) Uani 1.00 1 d . . . C8 C 0.5722(1) 0.0248(3) 0.6961(1) 0.0559(5) Uani 1.00 1 d . . . C9 C 0.7023(1) 0.3986(3) 0.82347(9) 0.0427(4) Uani 1.00 1 d . . . C10 C 0.6684(1) 0.2028(2) 0.81846(9) 0.0409(4) Uani 1.00 1 d . . . C11 C 0.6211(1) 0.1786(3) 0.73914(9) 0.0447(4) Uani 1.00 1 d . . . C12 C 0.6291(1) 0.3617(3) 0.70356(9) 0.0479(5) Uani 1.00 1 d . . . C13 C 0.8832(1) 0.3308(2) 1.07423(9) 0.0407(4) Uani 1.00 1 d . . . C14 C 0.8731(1) 0.2791(3) 1.1511(1) 0.0523(5) Uani 1.00 1 d . . . C15 C 0.9514(2) 0.1684(3) 1.1926(1) 0.0661(6) Uani 1.00 1 d . . . C16 C 1.0360(2) 0.1069(3) 1.1579(1) 0.0667(6) Uani 1.00 1 d . . . C17 C 1.0441(1) 0.1540(3) 1.0817(1) 0.0594(6) Uani 1.00 1 d . . . C18 C 0.9682(1) 0.2660(3) 1.0396(1) 0.0489(5) Uani 1.00 1 d . . . C19 C 0.7706(1) 0.6261(3) 1.0550(1) 0.0472(4) Uani 1.00 1 d . . . C20 C 0.8286(2) 0.7184(3) 1.1260(1) 0.0694(6) Uani 1.00 1 d . . . H1 H 0.6611(1) -0.0476(2) 0.88360(9) 0.051(1) Uiso 1.00 1 c . . . H2 H 0.7364(1) 0.0911(2) 0.99975(9) 0.050(1) Uiso 1.00 1 c . . . H3 H 0.7731(1) 0.6161(3) 0.89145(9) 0.054(1) Uiso 1.00 1 c . . . H4 H 0.5967(1) 0.5279(4) 0.6049(1) 0.072(1) Uiso 1.00 1 c . . . H5 H 0.5119(2) 0.2687(4) 0.5344(1) 0.081(1) Uiso 1.00 1 c . . . H6 H 0.4979(2) -0.0393(4) 0.5896(1) 0.082(1) Uiso 1.00 1 c . . . H7 H 0.5666(1) -0.1025(3) 0.7182(1) 0.067(1) Uiso 1.00 1 c . . . H8 H 0.8137(1) 0.3185(3) 1.1748(1) 0.062(1) Uiso 1.00 1 c . . . H9 H 0.9458(2) 0.1352(3) 1.2454(1) 0.077(1) Uiso 1.00 1 c . . . H10 H 1.0888(2) 0.0320(3) 1.1866(1) 0.077(1) Uiso 1.00 1 c . . . H11 H 1.1022(1) 0.1096(3) 1.0575(1) 0.070(1) Uiso 1.00 1 c . . . H12 H 0.9745(1) 0.2984(3) 0.9869(1) 0.059(1) Uiso 1.00 1 c . . . H13 H 0.8823(2) 0.6321(3) 1.1466(1) 0.082(1) Uiso 1.00 1 c . . . H14 H 0.8578(2) 0.8400(3) 1.1119(1) 0.083(1) Uiso 1.00 1 c . . . H15 H 0.7825(2) 0.7415(3) 1.1642(1) 0.082(1) Uiso 1.00 1 c . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.0604(8) 0.0514(7) 0.0418(6) -0.0083(6) -0.0037(5) 0.0049(5) O2 0.0673(9) 0.0495(7) 0.0610(8) 0.0161(6) -0.0053(6) -0.0022(6) N1 0.0449(7) 0.0383(7) 0.0434(7) 0.0020(6) -0.0052(5) -0.0029(6) C1 0.0435(8) 0.0345(8) 0.0492(9) -0.0034(6) 0.0031(7) -0.0025(7) C2 0.0446(9) 0.0365(8) 0.0439(8) 0.0005(6) 0.0021(6) 0.0039(6) C3 0.0384(8) 0.0378(8) 0.0420(8) -0.0001(6) -0.0022(6) -0.0029(6) C4 0.0483(9) 0.0387(8) 0.0478(9) -0.0075(7) -0.0017(7) 0.0013(7) C5 0.056(1) 0.081(1) 0.0428(9) 0.002(1) 0.0010(8) 0.0022(9) C6 0.054(1) 0.104(2) 0.042(1) -0.001(1) -0.0006(8) -0.011(1) C7 0.056(1) 0.097(2) 0.052(1) -0.014(1) 0.0051(8) -0.028(1) C8 0.049(1) 0.066(1) 0.053(1) -0.0111(9) 0.0098(8) -0.0189(9) C9 0.0435(8) 0.0434(8) 0.0407(8) -0.0029(7) 0.0018(6) 0.0039(7) C10 0.0357(8) 0.0420(9) 0.0447(8) -0.0019(6) 0.0027(6) -0.0055(7) C11 0.0371(8) 0.054(1) 0.0437(8) -0.0015(7) 0.0061(6) -0.0089(7) C12 0.0430(9) 0.059(1) 0.0409(8) -0.0024(7) 0.0030(6) -0.0048(8) C13 0.0420(8) 0.0349(8) 0.0435(8) -0.0034(6) -0.0041(6) -0.0017(6) C14 0.055(1) 0.054(1) 0.0459(9) -0.0042(8) -0.0004(7) 0.0002(8) C15 0.080(1) 0.062(1) 0.051(1) -0.008(1) -0.018(1) 0.0092(9) C16 0.062(1) 0.053(1) 0.078(1) 0.0030(9) -0.027(1) 0.001(1) C17 0.043(1) 0.048(1) 0.085(1) 0.0026(8) -0.0041(9) -0.010(1) C18 0.0474(9) 0.0434(9) 0.055(1) -0.0019(7) 0.0008(7) -0.0035(7) C19 0.0517(9) 0.0390(9) 0.0498(9) 0.0009(7) -0.0002(7) -0.0016(7) C20 0.081(1) 0.052(1) 0.071(1) 0.006(1) -0.013(1) -0.021(1) #============================================================================== _computing_data_collection 'PROCESS-AUTO' _computing_cell_refinement 'PROCESS-AUTO' _computing_data_reduction 'CrystalStructure' _computing_structure_solution 'SIR92' _computing_structure_refinement 'CRYSTALS' _computing_publication_material 'CrystalStructure Ver. 2.00' _computing_molecular_graphics ? #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C9 . 1.3801(18) yes O1 . C12 . 1.384(2) yes O2 . C19 . 1.217(2) yes N1 . C3 . 1.4417(18) yes N1 . C13 . 1.4343(19) yes N1 . C19 . 1.387(2) yes C1 . C2 . 1.383(2) yes C1 . C10 . 1.392(2) yes C2 . C3 . 1.402(2) yes C3 . C4 . 1.386(2) yes C4 . C9 . 1.377(2) yes C5 . C6 . 1.379(3) yes C5 . C12 . 1.383(2) yes C6 . C7 . 1.383(3) yes C7 . C8 . 1.389(3) yes C8 . C11 . 1.394(2) yes C9 . C10 . 1.398(2) yes C10 . C11 . 1.450(2) yes C11 . C12 . 1.394(3) yes C13 . C14 . 1.393(2) yes C13 . C18 . 1.382(2) yes C14 . C15 . 1.398(3) yes C15 . C16 . 1.372(3) yes C16 . C17 . 1.370(3) yes C17 . C18 . 1.386(3) yes C19 . C20 . 1.505(2) yes loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C9 . O1 . C12 . 105.39(13) yes C3 . N1 . C13 . 117.54(12) yes C3 . N1 . C19 . 119.29(12) yes C13 . N1 . C19 . 123.14(12) yes C2 . C1 . C10 . 119.09(15) yes C2 . C1 . H1 . 120.50(9) no C10 . C1 . H1 . 120.42(9) no C1 . C2 . C3 . 120.95(14) yes C1 . C2 . H2 . 119.55(9) no C3 . C2 . H2 . 119.51(9) no N1 . C3 . C2 . 118.83(14) yes N1 . C3 . C4 . 120.16(14) yes C2 . C3 . C4 . 121.01(14) yes C3 . C4 . C9 . 116.75(15) yes C3 . C4 . H3 . 121.68(9) no C9 . C4 . H3 . 121.6(1) no C6 . C5 . C12 . 116.2(2) yes C6 . C5 . H4 . 122.00(13) no C12 . C5 . H4 . 121.75(12) no C5 . C6 . C7 . 121.68(18) yes C5 . C6 . H5 . 119.08(13) no C7 . C6 . H5 . 119.24(11) no C6 . C7 . C8 . 121.58(19) yes C6 . C7 . H6 . 119.20(11) no C8 . C7 . H6 . 119.23(13) no C7 . C8 . C11 . 118.0(2) yes C7 . C8 . H7 . 121.07(13) no C11 . C8 . H7 . 120.97(11) no O1 . C9 . C4 . 124.24(15) yes O1 . C9 . C10 . 111.85(13) yes C4 . C9 . C10 . 123.87(15) yes C1 . C10 . C9 . 118.30(14) yes C1 . C10 . C11 . 136.30(15) yes C9 . C10 . C11 . 105.33(14) yes C8 . C11 . C10 . 135.38(17) yes C8 . C11 . C12 . 118.83(16) yes C10 . C11 . C12 . 105.78(14) yes O1 . C12 . C5 . 124.68(18) yes O1 . C12 . C11 . 111.62(14) yes C5 . C12 . C11 . 123.70(17) yes N1 . C13 . C14 . 120.97(15) yes N1 . C13 . C18 . 119.43(14) yes C14 . C13 . C18 . 119.58(16) yes C13 . C14 . C15 . 119.10(19) yes C13 . C14 . H8 . 120.3(1) no C15 . C14 . H8 . 120.56(13) no C14 . C15 . C16 . 120.75(19) yes C14 . C15 . H9 . 119.60(13) no C16 . C15 . H9 . 119.65(12) no C15 . C16 . C17 . 119.80(18) yes C15 . C16 . H10 . 120.10(12) no C17 . C16 . H10 . 120.10(12) no C16 . C17 . C18 . 120.51(19) yes C16 . C17 . H11 . 119.70(12) no C18 . C17 . H11 . 119.79(12) no C13 . C18 . C17 . 120.23(18) yes C13 . C18 . H12 . 119.7(1) no C17 . C18 . H12 . 120.03(12) no O2 . C19 . N1 . 121.36(15) yes O2 . C19 . C20 . 120.58(16) yes N1 . C19 . C20 . 118.01(15) yes C19 . C20 . H13 . 109.4(1) no C19 . C20 . H14 . 109.32(12) no C19 . C20 . H15 . 109.68(12) no loop_ _geom_torsion_atom_site_label_1 _geom_torsion_site_symmetry_1 _geom_torsion_atom_site_label_2 _geom_torsion_site_symmetry_2 _geom_torsion_atom_site_label_3 _geom_torsion_site_symmetry_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C12 . O1 . C9 . C4 . -177.2(2) yes C12 . O1 . C9 . C10 . 0.9(3) yes C9 . O1 . C12 . C5 . 177.9(2) yes C9 . O1 . C12 . C11 . -1.5(3) yes C13 . N1 . C3 . C2 . 46.8(3) yes C13 . N1 . C3 . C4 . -133.3(2) yes C19 . N1 . C3 . C2 . -131.4(2) yes C19 . N1 . C3 . C4 . 48.5(3) yes C3 . N1 . C13 . C14 . -124.6(2) yes C3 . N1 . C13 . C18 . 53.8(3) yes C19 . N1 . C13 . C14 . 53.6(3) yes C19 . N1 . C13 . C18 . -128.0(3) yes C3 . N1 . C19 . O2 . 5.3(3) yes C3 . N1 . C19 . C20 . -172.1(2) yes C13 . N1 . C19 . O2 . -172.9(2) yes C13 . N1 . C19 . C20 . 9.8(3) yes C10 . C1 . C2 . C3 . -0.8(3) yes C2 . C1 . C10 . C9 . 0.9(3) yes C2 . C1 . C10 . C11 . -175.8(2) yes C1 . C2 . C3 . N1 . 179.2(2) yes C1 . C2 . C3 . C4 . -0.7(3) yes N1 . C3 . C4 . C9 . -178.0(2) yes C2 . C3 . C4 . C9 . 1.9(3) yes C3 . C4 . C9 . O1 . 176.1(2) yes C3 . C4 . C9 . C10 . -1.8(3) yes C12 . C5 . C6 . C7 . -0.6(4) yes C6 . C5 . C12 . O1 . -179.4(2) yes C6 . C5 . C12 . C11 . -0.1(4) yes C5 . C6 . C7 . C8 . 0.3(4) yes C6 . C7 . C8 . C11 . 0.5(4) yes C7 . C8 . C11 . C10 . 177.3(2) yes C7 . C8 . C11 . C12 . -1.1(4) yes O1 . C9 . C10 . C1 . -177.7(2) yes O1 . C9 . C10 . C11 . -0.1(2) yes C4 . C9 . C10 . C1 . 0.4(3) yes C4 . C9 . C10 . C11 . 178.0(2) yes C1 . C10 . C11 . C8 . -2.4(5) yes C1 . C10 . C11 . C12 . 176.2(2) yes C9 . C10 . C11 . C8 . -179.4(3) yes C9 . C10 . C11 . C12 . -0.8(3) yes C8 . C11 . C12 . O1 . -179.7(2) yes C8 . C11 . C12 . C5 . 0.9(4) yes C10 . C11 . C12 . O1 . 1.4(3) yes C10 . C11 . C12 . C5 . -177.9(2) yes N1 . C13 . C14 . C15 . -179.2(2) yes C18 . C13 . C14 . C15 . 2.4(4) yes N1 . C13 . C18 . C17 . -179.9(2) yes C14 . C13 . C18 . C17 . -1.5(4) yes C13 . C14 . C15 . C16 . -1.6(4) yes C14 . C15 . C16 . C17 . -0.1(4) yes C15 . C16 . C17 . C18 . 1.0(4) yes C16 . C17 . C18 . C13 . -0.2(4) yes # End of CIF