data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Jye-Shane Yang' _publ_contact_author_address ; Department of Chemistry National Taiwan University No1 Roosevelt Rd Sec 4 Taipei 10617 TAIWAN ; _publ_contact_author_email JSYANG@NTU.EDU.TW _publ_section_title ; Photoisomerization of the Green Fluorescence Protein Chromophore and the meta- and para-Amino Analogues ; loop_ _publ_author_name 'Jye-Shane Yang' 'Guan-Jhih Huang' 'Gene-Hsiang Lee' 'Shie-ming Peng' # Attachment 'm-ABDI-new.cif' data_m-ABDI _database_code_depnum_ccdc_archive 'CCDC 667977' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H13 N3 O' _chemical_formula_weight 215.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 10.5533(2) _cell_length_b 14.0126(3) _cell_length_c 15.1145(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2235.12(8) _cell_formula_units_Z 8 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 30136 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.279 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 912 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.900 _exptl_absorpt_correction_T_max 0.993 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14829 _diffrn_reflns_av_R_equivalents 0.0387 _diffrn_reflns_av_sigmaI/netI 0.0245 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.77 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2546 _reflns_number_gt 1924 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius BV)' _computing_cell_refinement 'HKL Denzo & Scalepack (Otwinowski & Minor)' _computing_data_reduction 'HKL Denzo & Scalepack (Otwinowski & Minor)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0852P)^2^+0.6193P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.033(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2546 _refine_ls_number_parameters 148 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0743 _refine_ls_R_factor_gt 0.0564 _refine_ls_wR_factor_ref 0.1799 _refine_ls_wR_factor_gt 0.1667 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.084 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 0.19187(14) 0.57391(11) 0.04428(12) 0.0779(5) Uani 1 1 d . . . N1 N 0.84041(18) 0.78223(13) 0.07580(15) 0.0811(6) Uani 1 1 d . . . H1A H 0.9194 0.7930 0.0854 0.097 Uiso 1 1 calc R . . H1B H 0.7952 0.8238 0.0483 0.097 Uiso 1 1 calc R . . N2 N 0.20831(16) 0.42370(12) 0.10643(12) 0.0624(5) Uani 1 1 d . . . N3 N 0.41678(16) 0.41543(11) 0.13950(11) 0.0597(5) Uani 1 1 d . . . C1 C 0.60194(18) 0.59396(12) 0.11338(12) 0.0511(5) Uani 1 1 d . . . C2 C 0.65943(18) 0.67866(13) 0.08626(12) 0.0541(5) Uani 1 1 d . . . H2A H 0.6118 0.7233 0.0551 0.065 Uiso 1 1 calc R . . C3 C 0.78619(18) 0.69834(13) 0.10451(13) 0.0569(5) Uani 1 1 d . . . C4 C 0.8557(2) 0.62968(15) 0.14899(14) 0.0635(5) Uani 1 1 d . . . H4A H 0.9412 0.6400 0.1601 0.076 Uiso 1 1 calc R . . C5 C 0.7993(2) 0.54619(15) 0.17698(14) 0.0645(6) Uani 1 1 d . . . H5A H 0.8473 0.5018 0.2081 0.077 Uiso 1 1 calc R . . C6 C 0.6735(2) 0.52702(14) 0.15988(14) 0.0607(5) Uani 1 1 d . . . H6A H 0.6369 0.4703 0.1791 0.073 Uiso 1 1 calc R . . C7 C 0.46819(18) 0.58101(13) 0.09144(13) 0.0562(5) Uani 1 1 d . . . H7A H 0.4304 0.6339 0.0653 0.067 Uiso 1 1 calc R . . C8 C 0.39049(18) 0.50643(12) 0.10233(12) 0.0535(5) Uani 1 1 d . . . C9 C 0.2544(2) 0.51040(14) 0.07884(13) 0.0597(5) Uani 1 1 d . . . C10 C 0.3079(2) 0.37160(14) 0.14027(14) 0.0608(5) Uani 1 1 d . . . C11 C 0.0765(2) 0.39477(19) 0.0978(2) 0.0838(7) Uani 1 1 d . . . H11A H 0.0269 0.4479 0.0777 0.126 Uiso 1 1 calc R . . H11B H 0.0454 0.3737 0.1543 0.126 Uiso 1 1 calc R . . H11C H 0.0703 0.3435 0.0559 0.126 Uiso 1 1 calc R . . C12 C 0.2893(3) 0.27301(17) 0.1745(2) 0.0883(8) Uani 1 1 d . . . H12A H 0.2781 0.2299 0.1258 0.132 Uiso 1 1 calc R . . H12B H 0.2156 0.2713 0.2117 0.132 Uiso 1 1 calc R . . H12C H 0.3623 0.2542 0.2082 0.132 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0606(9) 0.0640(9) 0.1092(13) 0.0078(9) -0.0034(8) 0.0010(7) N1 0.0625(11) 0.0645(12) 0.1162(16) 0.0258(11) -0.0082(10) -0.0117(9) N2 0.0602(10) 0.0523(9) 0.0746(11) -0.0067(8) 0.0118(8) -0.0088(7) N3 0.0646(10) 0.0472(9) 0.0673(10) -0.0008(7) 0.0081(8) -0.0007(7) C1 0.0557(10) 0.0429(9) 0.0546(9) -0.0004(7) 0.0029(8) 0.0009(7) C2 0.0548(10) 0.0458(9) 0.0617(11) 0.0051(8) 0.0006(8) 0.0046(8) C3 0.0560(11) 0.0507(10) 0.0641(11) 0.0023(8) 0.0034(8) -0.0015(8) C4 0.0536(11) 0.0658(12) 0.0711(12) 0.0034(10) -0.0060(9) 0.0029(9) C5 0.0646(12) 0.0591(12) 0.0698(12) 0.0106(10) -0.0081(10) 0.0070(9) C6 0.0678(13) 0.0472(10) 0.0672(12) 0.0080(8) -0.0014(10) 0.0003(9) C7 0.0564(11) 0.0465(9) 0.0658(11) 0.0042(8) 0.0038(8) 0.0036(8) C8 0.0556(10) 0.0457(9) 0.0591(10) -0.0009(8) 0.0060(8) -0.0004(8) C9 0.0576(11) 0.0510(10) 0.0705(12) -0.0043(9) 0.0073(9) -0.0012(9) C10 0.0699(13) 0.0473(10) 0.0652(12) -0.0037(8) 0.0108(9) -0.0061(9) C11 0.0622(14) 0.0785(15) 0.1108(19) -0.0082(14) 0.0105(13) -0.0172(12) C12 0.1003(19) 0.0570(13) 0.1077(19) 0.0134(12) 0.0079(15) -0.0149(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C9 1.225(3) . ? N1 C3 1.377(2) . ? N1 H1A 0.8600 . ? N1 H1B 0.8600 . ? N2 C9 1.373(3) . ? N2 C10 1.378(3) . ? N2 C11 1.454(3) . ? N3 C10 1.303(3) . ? N3 C8 1.421(2) . ? C1 C6 1.394(3) . ? C1 C2 1.395(2) . ? C1 C7 1.461(3) . ? C2 C3 1.394(3) . ? C2 H2A 0.9300 . ? C3 C4 1.384(3) . ? C4 C5 1.379(3) . ? C4 H4A 0.9300 . ? C5 C6 1.380(3) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C8 1.339(3) . ? C7 H7A 0.9300 . ? C8 C9 1.481(3) . ? C10 C12 1.488(3) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? 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_3 _geom_angle_publ_flag C3 N1 H1A 120.0 . . ? C3 N1 H1B 120.0 . . ? H1A N1 H1B 120.0 . . ? C9 N2 C10 108.15(17) . . ? C9 N2 C11 123.9(2) . . ? C10 N2 C11 127.91(19) . . ? C10 N3 C8 104.72(17) . . ? C6 C1 C2 119.03(18) . . ? C6 C1 C7 123.63(17) . . ? C2 C1 C7 117.33(16) . . ? C3 C2 C1 121.86(17) . . ? C3 C2 H2A 119.1 . . ? C1 C2 H2A 119.1 . . ? N1 C3 C4 121.76(19) . . ? N1 C3 C2 120.35(18) . . ? C4 C3 C2 117.85(18) . . ? C5 C4 C3 120.71(19) . . ? C5 C4 H4A 119.6 . . ? C3 C4 H4A 119.6 . . ? C4 C5 C6 121.52(19) . . ? C4 C5 H5A 119.2 . . ? C6 C5 H5A 119.2 . . ? C5 C6 C1 119.00(18) . . ? C5 C6 H6A 120.5 . . ? C1 C6 H6A 120.5 . . ? C8 C7 C1 131.35(18) . . ? C8 C7 H7A 114.3 . . ? C1 C7 H7A 114.3 . . ? C7 C8 N3 129.03(19) . . ? C7 C8 C9 122.37(17) . . ? N3 C8 C9 108.54(16) . . ? O1 C9 N2 125.5(2) . . ? O1 C9 C8 130.71(19) . . ? N2 C9 C8 103.73(17) . . ? N3 C10 N2 114.81(17) . . ? N3 C10 C12 123.8(2) . . ? N2 C10 C12 121.39(19) . . ? N2 C11 H11A 109.5 . . ? N2 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N2 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.249 _refine_diff_density_min -0.181 _refine_diff_density_rms 0.033