# Copyright The Royal Society of Chemistry, 1999 # CCDC Number: 182/1211 data_global # 1. SUBMISSION DETAILS _publ_contact_author # Name and address of author for correspondence ; Professor Ming Chang P. Yeh Department of Chemistry National Taiwan Normal University 88, Sec. 4, Ding-Jou Road, Taipai 117, Taiwan Republic of China. ; _publ_contact_author_phone '886 2 2933 1186 ext 301' _publ_contact_author_fax '886 2 2932 4249' _publ_contact_author_email 'cheyeh@scc.ntnu.edu.tw' _publ_requested_journal 'J. Chem. Soc. Chem. Commun.' _publ_requested_coeditor_name ? #======================================================================= data_1 # 1. CHEMICAL DATA _chemical_name_systematic ; _chemical_name_common ? _chemical_formula_moiety 'C8 H9 N O3' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C8 H9 N O3' _chemical_formula_weight 167.16 _chemical_melting_point ? _chemical_compound_source ? # 2. CRYSTAL DATA _symmetry_cell_setting 'Monoclinic' _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz 'x,y,z' '-x,-y,-z' '-x,1/2+y,1/2-z' 'x,1/2-y,1/2+z' _cell_length_a 9.535(2) _cell_length_b 7.052(1) _cell_length_c 12.691(3) _cell_angle_alpha _cell_angle_beta 112.0(2) _cell_angle_gamma _cell_volume 791.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 12.49 _cell_measurement_theta_max 14.25 _cell_special_details ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.403 _exptl_crystal_density_method ? _exptl_crystal_F_000 351.94 _exptl_absorpt_coefficient_mu 0.10 _exptl_absorpt_correction_type ' empirical via \y rotation ' _exptl_absorpt_correction_T_min .972 _exptl_absorpt_correction_T_max .999 # 3. EXPERIMENTAL DATA _exptl_special_details ? _diffrn_ambient_temperature 298 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source x-ray_tube _diffrn_radiation_monochromator graphite _diffrn_measurement_device ' CAD-4 diffractometer ' _diffrn_measurement_method \w--2\q _diffrn_standards_number 3 _diffrn_standards_interval_count 300 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -6 -2 0 2 4 -5 5 -1 -7 _diffrn_reflns_number 2395 _diffrn_reflns_av_R_equivalents 0.012 _diffrn_reflns_av_sigmaI/netI ? _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.5 _diffrn_reflns_theta_max 30.0 _diffrn_reflns_reduction_process ? _computing_data_collection 'Nonius' _computing_cell_refinement 'Nonius' _computing_data_reduction 'NRCVAX' _computing_structure_solution 'NRCVAX' _computing_structure_refinement 'NRCVAX' _computing_molecular_graphics 'ORTEP' _computing_publication_material 'NRCVAX' # 4. REFINEMENT DATA _refine_special_details ? _reflns_number_total 2395 _reflns_number_observed 2298 _reflns_observed_criterion F>2.5\s(F) _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme 'W = 1/[\s^2^(F)]' _refine_ls_hydrogen_treatment 'noref' _refine_ls_extinction_method Secondary _refine_ls_extinction_coef 0.164 _refine_ls_extinction_expression ? _refine_ls_abs_structure_details ? ; _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1490 _refine_ls_number_parameters 110 _refine_ls_number_restraints ? _refine_ls_number_constraints ? _refine_ls_R_factor_all .078 _refine_ls_R_factor_obs .040 _refine_ls_wR_factor_all .050 _refine_ls_wR_factor_obs .039 _refine_ls_goodness_of_fit_all ? _refine_ls_goodness_of_fit_obs 3.75 _refine_ls_shift/esd_max 0.003 _refine_ls_shift/esd_mean ? _refine_diff_density_max .230 _refine_diff_density_min -.180 # 5. ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_B_iso_or_equiv _atom_site_thermal_displace_type _atom_site_type_symbol O1 0.1940(2) 0.4190(2) 0.4207(1) 4.59(9) Biso O O2 -0.5143(2) 0.2348(2) -0.0118(1) 4.11(8) Biso O O3 -0.4827(1) 0.2560(3) 0.1698(1) 4.40(8) Biso O N1 0.1104(2) 0.2562(3) 0.4196(1) 3.81(9) Biso N C1 -0.0332(2) 0.2876(3) 0.3734(2) 3.2(1) Biso C C2 -0.1048(2) 0.4733(3) 0.3271(2) 3.5(1) Biso C C3 -0.2663(2) 0.4511(3) 0.2404(2) 3.35(9) Biso C C4 -0.2811(2) 0.3679(3) 0.1259(2) 2.98(9) Biso C C5 -0.4348(2) 0.2804(3) 0.0837(2) 3.31(9) Biso C C6 -0.3613(2) 0.3135(4) 0.2774(2) 4.3(1) Biso C C7 -0.2774(3) 0.1389(4) 0.3317(2) 4.8(1) Biso C C8 -0.1286(3) 0.1281(3) 0.3724(2) 4.5(1) Biso C H2 -0.108 0.560 0.396 4.3 Biso H H2' -0.039 0.543 0.285 4.3 Biso H H3 -0.320 0.588 0.226 4.1 Biso H H4 -0.195 0.262 0.136 3.7 Biso H H4' -0.274 0.478 0.069 3.7 Biso H H6 -0.409 0.384 0.332 5.1 Biso H H7 -0.343 0.017 0.335 5.5 Biso H H8 -0.078 -0.006 0.406 5.0 Biso H HO1 0.295 0.375 0.459 5.3 Biso 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 5.81(9) 5.8(1) 5.8(1) 0.00(8) 2.17(8) 0.00(9) O O2 5.21(8) 5.2(1) 5.2(9) 0.00(8) 1.95(7) 0.00(9) O O3 5.57(8) 5.6(1) 5.6(1) 0.00(8) 2.08(7) 0.00(9) O N1 4.8(1) 4.8(1) 4.8(1) 0.0(1) 1.81(9) 0.0(1) N C1 4.1(1) 4.1(1) 4.1(1) 0.0(1) 1.53(9) 0.0(9) C C2 4.4(1) 4.4(1) 4.4(1) 0.0(1) 1.6(1) 0.0(1) C C3 4.0(1) 4.2(1) 4.3(1) 0.6(1) 1.21(9) -0.1(1) C C4 3.2(1) 4.0(1) 3.8(1) 0.05(9) 1.06(9) 0.38(9) C C5 3.6(1) 4.1(1) 4.5(1) 0.6(1) 1.11(9) 0.6(1) C C6 4.5(1) 8.2(2) 4.0(1) -0.1(1) 1.9(1) -0.4(1) C C7 5.9(2) 7.6(2) 4.4(1) -1.6(1) 1.4(1) 1.7(1) C C8 6.3(2) 5.4(2) 4.3(1) -0.4(1) 0.7(1) 1.7(1) C # 6. MOLEC ULAR GEOMETRY _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 O(1) N(1) 1.395(2) . . yes O(1) HO(1) 0.949(2) . . yes O(2) C(5) 1.208(4) . . yes O(3) C(5) 1.344(3) . . yes O(3) C(6) 1.478(4) . . yes N(1) C(1) 1.291(3) . . yes C(1) C(2) 1.492(3) . . yes C(1) C(8) 1.443(3) . . yes C(2) C(3) 1.529(5) . . yes C(2) H(2) 1.080(2) . . yes C(2) H(2') 1.080(2) . . yes C(3) C(4) 1.524(3) . . yes C(3) C(6) 1.517(3) . . yes C(3) H(3) 1.080(2) . . yes C(4) C(5) 1.492(3) . . yes C(4) H(4) 1.081(2) . . yes C(4) H(4') 1.080(2) . . yes C(6) C(7) 1.490(4) . . yes C(6) H(6) 1.082(2) . . yes C(7) C(8) 1.318(4) . . yes C(7) H(7) 1.076(2) . . yes C(8) H(8) 1.076(2) . . yes 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 N(1) O(1) HO(1) 101.5(2) . . . yes C(5) O(3) C(6) 109.3(2) . . . yes O(1) N(1) C(1) 111.7(2) . . . yes N(1) C(1) C(2) 125.4(2) . . . yes N(1) C(1) C(8) 115.4(2) . . . yes C(2) C(1) C(8) 119.1(2) . . . yes C(1) C(2) C(3) 112.5(2) . . . yes C(1) C(2) H(2) 109.0(2) . . . yes C(1) C(2) H(2') 109.1(2) . . . yes C(3) C(2) H(2) 108.4(2) . . . yes C(3) C(2) H(2') 108.0(2) . . . yes H(2) C(2) H(2') 109.8(2) . . . yes C(2) C(3) C(4) 115.8(2) . . . yes C(2) C(3) C(6) 113.6(2) . . . yes C(2) C(3) H(3) 108.5(2) . . . yes C(4) C(3) C(6) 101.3(2) . . . yes C(4) C(3) H(3) 108.6(2) . . . yes C(6) C(3) H(3) 108.9(2) . . . yes C(3) C(4) C(5) 103.3(2) . . . yes C(3) C(4) H(4) 110.9(2) . . . yes C(3) C(4) H(4') 110.8(2) . . . yes C(5) C(4) H(4) 110.8(2) . . . yes C(5) C(4) H(4') 110.8(2) . . . yes H(4) C(4) H(4') 110.1(2) . . . yes O(2) C(5) O(3) 120.4(2) . . . yes O(2) C(5) C(4) 129.3(2) . . . yes O(3) C(5) C(4) 110.3(2) . . . yes O(3) C(6) C(3) 103.9(2) . . . yes O(3) C(6) C(7) 107.5(2) . . . yes O(3) C(6) H(6) 110.3(2) . . . yes C(3) C(6) C(7) 113.1(2) . . . yes C(3) C(6) H(6) 110.4(2) . . . yes C(7) C(6) H(6) 111.4(2) . . . yes C(6) C(7) C(8) 122.9(2) . . . yes C(6) C(7) H(7) 117.4(2) . . . yes C(8) C(7) H(7) 119.7(2) . . . yes C(1) C(8) C(7) 122.7(2) . . . yes C(1) C(8) H(8) 119.5(2) . . . yes C(7) C(8) H(8) 117.8(2) . . . yes