# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2001 data_General _audit_creation_date 'Tue Sep 25 12:14:47 2001' _audit_creation_method 'by teXsan' _audit_update_record ? #------------------------------------------------------------------------------ # PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_coeditor_code ? #------------------------------------------------------------------------------ _journal_coden_Cambridge 207 _publ_requested_journal 'Perkin Transactions 1' loop_ _publ_author_name 'Kyu-Tae Chang' 'Yong Hyun Choi' 'Young-Kook Kim' 'Hyun Sun Lee' 'Woo Song Lee' _publ_contact_author_name 'Prof Yong-Jin Yoon' _publ_contact_author_email 'wslee@mail.kaist.ac.kr' _publ_section_title ; Regioselective synthesis of pyrazoles via the ring cleavage of 3-substituted N-alkylated-3-hydroxyisoindolin-1-ones. ; _publ_section_references ; Johnson, C. K. (1976). ORTEP-II. A FORTRAN Thermal-Ellipsoid Plot Program. Report ORNL-5138. Oak Ridge National Laboratory. Tennessee, USA. MSC & Rigaku. (1999). teXsan. Single Crystal Structure Analysis Software. Version 1.10. Molecular Structure Corporation, Texsas, USA and Rigaku Corporation, Tokyo, Japan. Rigaku (1998). PROCESS-AUTO. Automatic Data Acquisition and Processing Package for Imaging Plate Diffractometer. Rigaku Corporation, Tokyo, Japan Sheldrick, G. M. (1985). SHELXS86. Program for the Solution of Crystal Structures. Univ. of Gottingen, Germany. Zachariasen, W. H. (1967). Acta Cryst. 23, 558-564. ; #------------------------------------------------------------------------------ data_RGK485raplt_Gyeongsang_Nat _database_code_CSD 172539 #------------------------------------------------------------------------------ # CHEMICAL DATA _chemical_formula_sum 'C14 H17 N3 O ' _chemical_formula_moiety ? _chemical_formula_weight 243.31 _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,1/2+y,1/2-z -x,-y,-z x,1/2-y,1/2+z _cell_length_a 10.922(2) _cell_length_b 9.557(1) _cell_length_c 13.551(3) _cell_angle_alpha 90 _cell_angle_beta 113.20(1) _cell_angle_gamma 90 _cell_volume 1300.0(4) _cell_formula_units_Z 4 _cell_measurement_reflns_used 4520 _cell_measurement_theta_min 2.7 _cell_measurement_theta_max 27.25 _cell_measurement_temperature 123.2 #------------------------------------------------------------------------------ _exptl_crystal_description 'platelet' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.080 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.243 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type none #------------------------------------------------------------------------------ # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID Imaging Plate' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_reflns_number 9135 _diffrn_reflns_av_R_equivalents 0.031 _diffrn_reflns_theta_max 27.25 _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.25 _diffrn_measured_fraction_theta_full 0.990 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 #------------------------------------------------------------------------------ # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > -3.0 sigma(F^2^). The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 2890 _reflns_number_gt 2052 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0580 _refine_ls_wR_factor_ref 0.1538 _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 2890 _refine_ls_number_parameters 164 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^) + (0.08400(Max(Fo^2^,0) + 2Fc^2^)/3)^2^]' _refine_ls_shift/su_max 0.0001 _refine_diff_density_max 0.43 _refine_diff_density_min -0.47 _refine_ls_extinction_method 'Zachariasen(1967) type 2 Gaussian isotropic' _refine_ls_extinction_coef 0.020(5) _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? 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, Tables 4.2.6.8 and 6.1.1.1) ; 'H' 'H' 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; 'N' 'N' 0.006 0.003 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'O' 'O' 0.011 0.006 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ # 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 0.7166(1) 0.2059(2) 0.1720(1) 0.0188(3) Uani 1.00 d . . . N1 N 0.4639(2) 0.5955(2) 0.2507(1) 0.0183(4) Uani 1.00 d . . . N2 N 0.3945(2) 0.5136(2) 0.1662(1) 0.0176(4) Uani 1.00 d . . . N3 N 0.7426(1) 0.2814(2) 0.0225(1) 0.0155(4) Uani 1.00 d . . . C1 C 0.4395(2) 0.3466(2) 0.0514(1) 0.0142(4) Uani 1.00 d . . . C2 C 0.5215(2) 0.2625(2) 0.0174(1) 0.0142(4) Uani 1.00 d . . . C3 C 0.4656(2) 0.1749(2) -0.0714(2) 0.0190(5) Uani 1.00 d . . . C4 C 0.3286(2) 0.1658(2) -0.1266(2) 0.0234(5) Uani 1.00 d . . . C5 C 0.2468(2) 0.2465(2) -0.0935(2) 0.0214(5) Uani 1.00 d . . . C6 C 0.3013(2) 0.3357(2) -0.0072(2) 0.0180(5) Uani 1.00 d . . . C7 C 0.4873(2) 0.4445(2) 0.1431(1) 0.0153(4) Uani 1.00 d . . . C8 C 0.6158(2) 0.4842(2) 0.2146(2) 0.0210(5) Uani 1.00 d . . . C9 C 0.5958(2) 0.5804(2) 0.2816(2) 0.0230(5) Uani 1.00 d . . . C10 C 0.6695(2) 0.2501(2) 0.0786(1) 0.0143(4) Uani 1.00 d . . . C11 C 0.8889(2) 0.2641(2) 0.0599(2) 0.0205(5) Uani 1.00 d . . . C12 C 0.9600(2) 0.3642(3) 0.1525(2) 0.0289(6) Uani 1.00 d . . . C13 C 0.9272(2) 0.1127(3) 0.0936(2) 0.0341(7) Uani 1.00 d . . . C14 C 0.9223(2) 0.3000(3) -0.0360(2) 0.0319(6) Uani 1.00 d . . . H1N H 0.4239 0.6570 0.2845 0.0220 Uiso 1.00 calc . . . H3 H 0.5222 0.1205 -0.0945 0.0227 Uiso 1.00 calc . . . H3N H 0.6968 0.3181 -0.0476 0.0185 Uiso 1.00 calc . . . H4 H 0.2915 0.1048 -0.1864 0.0281 Uiso 1.00 calc . . . H5 H 0.1528 0.2406 -0.1303 0.0257 Uiso 1.00 calc . . . H6 H 0.2435 0.3917 0.0134 0.0216 Uiso 1.00 calc . . . H8 H 0.6986 0.4512 0.2161 0.0252 Uiso 1.00 calc . . . H9 H 0.6630 0.6277 0.3393 0.0276 Uiso 1.00 calc . . . H12a H 1.0536 0.3529 0.1758 0.0347 Uiso 1.00 calc . . . H12b H 0.9364 0.4578 0.1292 0.0347 Uiso 1.00 calc . . . H12c H 0.9342 0.3443 0.2103 0.0347 Uiso 1.00 calc . . . H13a H 1.0189 0.0991 0.1083 0.0410 Uiso 1.00 calc . . . H13b H 0.9114 0.0928 0.1563 0.0410 Uiso 1.00 calc . . . H13c H 0.8750 0.0518 0.0373 0.0410 Uiso 1.00 calc . . . H14a H 0.8816 0.3864 -0.0660 0.0383 Uiso 1.00 calc . . . H14b H 1.0161 0.3078 -0.0134 0.0383 Uiso 1.00 calc . . . H14c H 0.8900 0.2282 -0.0885 0.0383 Uiso 1.00 calc . . . 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 0.0186(6) 0.0215(8) 0.0170(7) 0.0023(6) 0.0078(5) 0.0050(6) N1 0.0233(8) 0.0199(9) 0.0137(8) 0.0017(7) 0.0093(6) -0.0028(7) N2 0.0196(7) 0.0203(9) 0.0140(7) 0.0017(7) 0.0077(6) -0.0024(7) N3 0.0124(7) 0.0206(9) 0.0140(8) 0.0024(7) 0.0058(6) 0.0029(7) C1 0.0162(8) 0.0143(9) 0.0141(9) 0.0001(8) 0.0080(7) 0.0019(7) C2 0.0138(8) 0.0151(10) 0.0145(9) -0.0009(7) 0.0064(7) 0.0015(7) C3 0.0200(9) 0.018(1) 0.022(1) 0.0009(8) 0.0118(8) -0.0025(8) C4 0.0212(9) 0.027(1) 0.021(1) -0.0051(9) 0.0066(8) -0.0092(9) C5 0.0135(8) 0.027(1) 0.022(1) -0.0037(8) 0.0053(7) -0.0024(9) C6 0.0166(9) 0.022(1) 0.0188(10) 0.0025(8) 0.0107(7) 0.0013(8) C7 0.0181(9) 0.0145(9) 0.0159(9) 0.0010(8) 0.0095(7) 0.0027(7) C8 0.0173(9) 0.022(1) 0.024(1) -0.0025(8) 0.0089(8) -0.0061(9) C9 0.0226(10) 0.025(1) 0.021(1) -0.0022(9) 0.0080(8) -0.0046(9) C10 0.0158(8) 0.0112(9) 0.0168(9) 0.0005(7) 0.0072(7) -0.0008(7) C11 0.0121(8) 0.028(1) 0.023(1) 0.0030(8) 0.0091(7) 0.0043(9) C12 0.0170(9) 0.041(1) 0.024(1) -0.0044(10) 0.0030(8) 0.0033(10) C13 0.025(1) 0.033(1) 0.049(2) 0.012(1) 0.020(1) 0.009(1) C14 0.0200(9) 0.052(2) 0.030(1) 0.001(1) 0.0167(9) 0.004(1) #------------------------------------------------------------------------------ _computing_data_collection 'PROCESS-AUTO (Rigaku, 1998)' _computing_cell_refinement 'PROCESS-AUTO (Rigaku, 1998)' _computing_data_reduction 'teXsan (MSC & Rigaku, 1999)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1985)' _computing_structure_refinement 'teXsan (MSC & Rigaku, 1999)' _computing_publication_material 'teXsan (MSC & Rigaku, 1999)' _computing_molecular_graphics 'ORTEP (Johnson, 1976)' #------------------------------------------------------------------------------ _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 C10 1.238(2) . . yes N1 N2 1.347(2) . . yes N1 C9 1.340(3) . . yes N1 H1N 0.950 . . no N2 C7 1.345(2) . . yes N3 C10 1.335(2) . . yes N3 C11 1.484(2) . . yes N3 H3N 0.950 . . no C1 C2 1.408(3) . . yes C1 C6 1.406(2) . . yes C1 C7 1.477(3) . . yes C2 C3 1.394(3) . . yes C2 C10 1.503(2) . . yes C3 C4 1.387(3) . . yes C3 H3 0.950 . . no C4 C5 1.383(3) . . yes C4 H4 0.950 . . no C5 C6 1.378(3) . . yes C5 H5 0.950 . . no C6 H6 0.950 . . no C7 C8 1.408(3) . . yes C8 C9 1.369(3) . . yes C8 H8 0.950 . . no C9 H9 0.950 . . no C11 C12 1.525(3) . . yes C11 C13 1.526(3) . . yes C11 C14 1.520(3) . . yes C12 H12a 0.950 . . no C12 H12b 0.950 . . no C12 H12c 0.950 . . no C13 H13a 0.950 . . no C13 H13b 0.950 . . no C13 H13c 0.950 . . no C14 H14a 0.950 . . no C14 H14b 0.950 . . no C14 H14c 0.950 . . 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 N2 N1 C9 112.2(2) . . . yes N2 N1 H1N 123.9 . . . no C9 N1 H1N 123.9 . . . no N1 N2 C7 105.1(1) . . . yes C10 N3 C11 125.9(2) . . . yes C10 N3 H3N 117.0 . . . no C11 N3 H3N 117.0 . . . no C2 C1 C6 116.9(2) . . . yes C2 C1 C7 125.3(2) . . . yes C6 C1 C7 117.8(2) . . . yes C1 C2 C3 120.4(2) . . . yes C1 C2 C10 123.3(2) . . . yes C3 C2 C10 116.0(2) . . . yes C2 C3 C4 121.1(2) . . . yes C2 C3 H3 119.5 . . . no C4 C3 H3 119.5 . . . no C3 C4 C5 119.2(2) . . . yes C3 C4 H4 120.4 . . . no C5 C4 H4 120.4 . . . no C4 C5 C6 120.1(2) . . . yes C4 C5 H5 119.9 . . . no C6 C5 H5 119.9 . . . no C1 C6 C5 122.2(2) . . . yes C1 C6 H6 118.9 . . . no C5 C6 H6 118.9 . . . no N2 C7 C1 117.3(2) . . . yes N2 C7 C8 110.2(2) . . . yes C1 C7 C8 132.5(2) . . . yes C7 C8 C9 105.1(2) . . . yes C7 C8 H8 127.4 . . . no C9 C8 H8 127.4 . . . no N1 C9 C8 107.4(2) . . . yes N1 C9 H9 126.3 . . . no C8 C9 H9 126.3 . . . no O1 C10 N3 123.9(2) . . . yes O1 C10 C2 121.0(2) . . . yes N3 C10 C2 115.0(2) . . . yes N3 C11 C12 109.9(2) . . . yes N3 C11 C13 109.8(2) . . . yes N3 C11 C14 105.8(2) . . . yes C12 C11 C13 111.0(2) . . . yes C12 C11 C14 110.3(2) . . . yes C13 C11 C14 109.9(2) . . . yes C11 C12 H12a 109.5 . . . no C11 C12 H12b 109.5 . . . no C11 C12 H12c 109.5 . . . no H12a C12 H12b 109.5 . . . no H12a C12 H12c 109.5 . . . no H12b C12 H12c 109.5 . . . no C11 C13 H13a 109.5 . . . no C11 C13 H13b 109.5 . . . no C11 C13 H13c 109.5 . . . no H13a C13 H13b 109.5 . . . no H13a C13 H13c 109.5 . . . no H13b C13 H13c 109.5 . . . no C11 C14 H14a 109.5 . . . no C11 C14 H14b 109.5 . . . no C11 C14 H14c 109.5 . . . no H14a C14 H14b 109.5 . . . no H14a C14 H14c 109.5 . . . no H14b C14 H14c 109.5 . . . no #------------------------------------------------------------------------------ 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 O1 N1 2.780(2) . 2_645 ? O1 N2 3.429(2) . 2_645 ? N1 C1 3.440(2) . 2_655 ? N1 C2 3.472(3) . 2_655 ? N1 C10 3.509(3) . 2_655 ? N1 C3 3.530(3) . 4_555 ? N1 C3 3.575(3) . 3_665 ? N1 C7 3.588(3) . 2_655 ? N2 N3 3.099(2) . 3_665 ? N2 C4 3.596(3) . 4_555 ? C1 C9 3.526(3) . 2_645 ? C2 C7 3.523(3) . 3_665 ? C3 C9 3.539(3) . 3_665 ? C4 C9 3.513(3) . 3_665 ? #------------------------------------------------------------------------------ loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_site_distance_DH _geom_hbond_site_distance_HA _geom_hbond_site_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag N1 H1N O1 . . 2_655 0.950 1.907 2.779(2) 151.549 no N3 H3N N2 . . 3_665 0.950 2.214 3.099(2) 154.637 no #------------------------------------------------------------------------------