#------------------------------------------------------------------------------ #$Date: 2009-11-16 03:43:51 +0200 (Mon, 16 Nov 2009) $ #$Revision: 853 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2204847.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2204847 _space_group_IT_number 15 _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _[local]_cod_cif_authors_sg_H-M 'C 2/c' loop_ _publ_author_name 'Gao, Shan' 'Huo, Li-Hua' 'Zhao, Hui' 'Ng, Seik Weng' _publ_section_title ; N-(2-Hydroxy-1-naphthalidene)phenylalanine ; _journal_issue 1 _journal_name_full 'Acta Crystallographica, Section E' _journal_page_first o192 _journal_page_last o194 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C20 H17 N O3' _chemical_formula_moiety 'C20 H17 N O3' _chemical_formula_sum 'C20 H17 N O3' _chemical_formula_weight 319.35 _chemical_name_common ; N-(2-Hydroxy-1-naphthalidene)phenylalanine ; _chemical_name_systematic ; (2-carboxy-1-phenylethyl)iminiomethylene-1-naphth-2-olate ; _symmetry_cell_setting Monoclinic _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90 _cell_angle_beta 123.01(3) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 25.152(5) _cell_length_b 9.760(2) _cell_length_c 15.557(3) _cell_measurement_reflns_used 12138 _cell_measurement_temperature 295(2) _cell_measurement_theta_max 27.5 _cell_measurement_theta_min 3.1 _cell_volume 3202.0(10) _computing_cell_refinement RAPID-AUTO _computing_data_collection 'RAPID-AUTO (Rigaku, 1998)' _computing_data_reduction 'CrystalStructure (Rigaku/MSC, 2002)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 295(2) _diffrn_measured_fraction_theta_full 0.99 _diffrn_measured_fraction_theta_max 0.99 _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.038 _diffrn_reflns_av_sigmaI/netI 0.034 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 14977 _diffrn_reflns_theta_full 27.5 _diffrn_reflns_theta_max 27.5 _diffrn_reflns_theta_min 3.1 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_T_max 0.986 _exptl_absorpt_correction_T_min 0.641 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(ABSCOR; Higashi, 1995)' _exptl_crystal_colour Yellow _exptl_crystal_density_diffrn 1.325 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Prism _exptl_crystal_F_000 1344 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.16 _refine_diff_density_max 0.23 _refine_diff_density_min -0.17 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.05 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 225 _refine_ls_number_reflns 3644 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.05 _refine_ls_R_factor_all 0.075 _refine_ls_R_factor_gt 0.048 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean <0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0623P)^2^+0.5726P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.115 _refine_ls_wR_factor_ref 0.127 _reflns_number_gt 2488 _reflns_number_total 3644 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file bt6572.cif loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' 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' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_type_symbol O1 0.14700(10) 0.62780(10) 0.62120(10) 0.0409(3) Uani d . 1 O O2 0.19170(10) 0.2962(2) 0.36820(10) 0.0568(4) Uani d . 1 O O3 0.09750(10) 0.31620(10) 0.22280(10) 0.0512(3) Uani d D 1 O N1 0.15620(10) 0.41700(10) 0.52690(10) 0.0352(3) Uani d D 1 N C1 0.19990(10) 0.6722(2) 0.63690(10) 0.0347(3) Uani d . 1 C C2 0.22850(10) 0.7944(2) 0.69520(10) 0.0420(4) Uani d . 1 C C3 0.28270(10) 0.8448(2) 0.70940(10) 0.0430(4) Uani d . 1 C C4 0.31530(10) 0.7794(2) 0.66890(10) 0.0377(4) Uani d . 1 C C5 0.37210(10) 0.8333(2) 0.68560(10) 0.0464(4) Uani d . 1 C C6 0.40270(10) 0.7715(2) 0.64580(10) 0.0500(4) Uani d . 1 C C7 0.37720(10) 0.6530(2) 0.58760(10) 0.0484(4) Uani d . 1 C C8 0.32240(10) 0.5971(2) 0.57120(10) 0.0415(4) Uani d . 1 C C9 0.29010(10) 0.6567(2) 0.61260(10) 0.0339(3) Uani d . 1 C C10 0.23230(10) 0.6007(2) 0.59830(10) 0.0327(3) Uani d . 1 C C11 0.20990(10) 0.4727(2) 0.55070(10) 0.0340(3) Uani d . 1 C C12 0.13670(10) 0.2762(2) 0.48760(10) 0.0359(4) Uani d . 1 C C13 0.09750(10) 0.2734(2) 0.37060(10) 0.0463(4) Uani d . 1 C C14 0.13490(10) 0.2969(2) 0.32190(10) 0.0396(4) Uani d . 1 C C15 0.10080(10) 0.2154(2) 0.53120(10) 0.0364(4) Uani d . 1 C C16 0.04290(10) 0.2691(2) 0.50550(10) 0.0489(4) Uani d . 1 C C17 0.01020(10) 0.2133(2) 0.54500(10) 0.0563(5) Uani d . 1 C C18 0.03530(10) 0.1033(2) 0.61080(10) 0.0556(5) Uani d . 1 C C19 0.09230(10) 0.0492(2) 0.63680(10) 0.0534(5) Uani d . 1 C C20 0.12530(10) 0.1049(2) 0.59750(10) 0.0441(4) Uani d . 1 C H3o 0.1190(10) 0.331(2) 0.1950(10) 0.066(6) Uiso d D 1 H H1n 0.1350(10) 0.469(2) 0.5410(10) 0.055(6) Uiso d D 1 H H2 0.2092 0.8401 0.7237 0.050 Uiso calc R 1 H H3 0.2995 0.9250 0.7471 0.052 Uiso calc R 1 H H5 0.3890 0.9126 0.7244 0.056 Uiso calc R 1 H H6 0.4402 0.8082 0.6575 0.060 Uiso calc R 1 H H7 0.3976 0.6113 0.5594 0.058 Uiso calc R 1 H H8 0.3062 0.5180 0.5319 0.050 Uiso calc R 1 H H11 0.2351 0.4237 0.5348 0.041 Uiso calc R 1 H H12 0.1751 0.2214 0.5121 0.043 Uiso calc R 1 H H13a 0.0764 0.1853 0.3480 0.056 Uiso calc R 1 H H13b 0.0648 0.3431 0.3458 0.056 Uiso calc R 1 H H16 0.0260 0.3436 0.4612 0.059 Uiso calc R 1 H H17 -0.0287 0.2498 0.5273 0.068 Uiso calc R 1 H H18 0.0133 0.0657 0.6376 0.067 Uiso calc R 1 H H19 0.1089 -0.0253 0.6810 0.064 Uiso calc R 1 H H20 0.1642 0.0678 0.6157 0.053 Uiso calc R 1 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 O1 0.0436(6) 0.0482(7) 0.0432(6) 0.0023(5) 0.0317(5) -0.0015(5) O2 0.0461(7) 0.0893(10) 0.0439(7) 0.0054(6) 0.0303(6) 0.0001(6) O3 0.0499(7) 0.0761(9) 0.0377(7) -0.0112(6) 0.0303(6) -0.0028(5) N1 0.0390(7) 0.0381(8) 0.0378(7) -0.0004(6) 0.0269(6) -0.0015(5) C1 0.0400(10) 0.0380(10) 0.0310(10) 0.0040(10) 0.0220(10) 0.0040(10) C2 0.0540(10) 0.0410(10) 0.0390(10) 0.0050(10) 0.0310(10) -0.0030(10) C3 0.0550(10) 0.0380(10) 0.0370(10) -0.0030(10) 0.0260(10) -0.0050(10) C4 0.0420(10) 0.0390(10) 0.0310(10) -0.0020(10) 0.0190(10) 0.0010(10) C5 0.0470(10) 0.0460(10) 0.0410(10) -0.0100(10) 0.0200(10) -0.0030(10) C6 0.0410(10) 0.0600(10) 0.0490(10) -0.0110(10) 0.0250(10) 0.0010(10) C7 0.0450(10) 0.0600(10) 0.0510(10) -0.0030(10) 0.0330(10) -0.0030(10) C8 0.0430(10) 0.0450(10) 0.0450(10) -0.0050(10) 0.0290(10) -0.0060(10) C9 0.0360(10) 0.0380(10) 0.0290(10) 0.0010(10) 0.0190(10) 0.0020(10) C10 0.0360(10) 0.0360(10) 0.0310(10) 0.0010(10) 0.0210(10) 0.0000(10) C11 0.0360(10) 0.0410(10) 0.0320(10) 0.0010(10) 0.0230(10) -0.0010(10) C12 0.0380(10) 0.0390(10) 0.0390(10) -0.0040(10) 0.0260(10) -0.0050(10) C13 0.0480(10) 0.0610(10) 0.0420(10) -0.0130(10) 0.0320(10) -0.0090(10) C14 0.0490(10) 0.0410(10) 0.0390(10) -0.0040(10) 0.0300(10) -0.0070(10) C15 0.0390(10) 0.0440(10) 0.0330(10) -0.0080(10) 0.0240(10) -0.0050(10) C16 0.0440(10) 0.0620(10) 0.0500(10) 0.0010(10) 0.0310(10) 0.0090(10) C17 0.0440(10) 0.0800(10) 0.0560(10) -0.0030(10) 0.0340(10) 0.0030(10) C18 0.0570(10) 0.0730(10) 0.0530(10) -0.0190(10) 0.0400(10) -0.0050(10) C19 0.0660(10) 0.0520(10) 0.0500(10) -0.0080(10) 0.0360(10) 0.0040(10) C20 0.0480(10) 0.0450(10) 0.0450(10) -0.0030(10) 0.0280(10) -0.0010(10) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 C1 1.291(2) yes O2 C14 1.201(2) yes O3 C14 1.310(2) yes N1 C11 1.306(2) yes N1 C12 1.475(2) yes C1 C10 1.429(2) yes C1 C2 1.432(2) yes C2 C3 1.349(2) yes C3 C4 1.428(2) yes C4 C5 1.407(2) yes C4 C9 1.414(2) yes C5 C6 1.362(3) yes C6 C7 1.391(3) yes C7 C8 1.372(2) yes C8 C9 1.408(2) yes C9 C10 1.453(2) yes C10 C11 1.405(2) yes C12 C15 1.514(2) yes C12 C13 1.527(2) yes C13 C14 1.512(2) yes C15 C20 1.383(2) yes C15 C16 1.387(2) yes C16 C17 1.380(2) yes C17 C18 1.376(3) yes C18 C19 1.366(3) yes C19 C20 1.383(2) yes O3 H3o 0.860(10) no N1 H1n 0.860(10) no C2 H2 0.93 no C3 H3 0.93 no C5 H5 0.93 no C6 H6 0.93 no C7 H7 0.93 no C8 H8 0.93 no C11 H11 0.93 no C12 H12 0.98 no C13 H13a 0.97 no C13 H13b 0.97 no C16 H16 0.93 no C17 H17 0.93 no C18 H18 0.93 no C19 H19 0.93 no C20 H20 0.93 no loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C11 N1 C12 124.30(10) yes O1 C1 C10 121.40(10) yes O1 C1 C2 120.70(10) yes C2 C1 C10 117.90(10) yes C1 C2 C3 121.4(2) yes C2 C3 C4 122.5(2) yes C5 C4 C9 119.9(2) yes C3 C4 C5 121.4(2) yes C3 C4 C9 118.70(10) yes C4 C5 C6 121.2(2) yes C5 C6 C7 119.4(2) yes C6 C7 C8 120.7(2) yes C7 C8 C9 121.5(2) yes C4 C9 C8 117.30(10) yes C4 C9 C10 119.10(10) yes C8 C9 C10 123.60(10) yes C1 C10 C11 119.90(10) yes C1 C10 C9 120.30(10) yes C9 C10 C11 119.80(10) yes N1 C11 C10 125.20(10) yes N1 C12 C15 109.00(10) yes N1 C12 C13 111.30(10) yes C13 C12 C15 111.70(10) yes C12 C13 C14 114.80(10) yes O2 C14 O3 124.2(2) yes O2 C14 C13 124.1(2) yes O3 C14 C13 111.60(10) yes C12 C15 C16 120.8(2) yes C12 C15 C20 120.50(10) yes C16 C15 C20 118.7(2) yes C15 C16 C17 120.7(2) yes C16 C17 C18 119.8(2) yes C17 C18 C19 120.2(2) yes C18 C19 C20 120.3(2) yes C15 C20 C19 120.3(2) yes C14 O3 H3o 112.0(10) no C11 N1 H1n 113.0(10) no C12 N1 H1n 123.0(10) no C3 C2 H2 119.3 no C1 C2 H2 119.3 no C2 C3 H3 118.8 no C4 C3 H3 118.8 no C6 C5 H5 119.4 no C4 C5 H5 119.4 no C5 C6 H6 120.3 no C7 C6 H6 120.3 no C8 C7 H7 119.7 no C6 C7 H7 119.7 no C7 C8 H8 119.2 no C9 C8 H8 119.2 no N1 C11 H11 117.4 no C10 C11 H11 117.4 no N1 C12 H12 108.2 no C15 C12 H12 108.2 no C13 C12 H12 108.2 no C14 C13 H13a 108.6 no C12 C13 H13a 108.6 no C14 C13 H13b 108.6 no C12 C13 H13b 108.6 no H13a C13 H13b 107.5 no C17 C16 H16 119.7 no C15 C16 H16 119.7 no C18 C17 H17 120.1 no C16 C17 H17 120.1 no C19 C18 H18 119.9 no C17 C18 H18 119.9 no C18 C19 H19 119.9 no C20 C19 H19 119.9 no C15 C20 H20 119.8 no C19 C20 H20 119.8 no loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_publ_flag O1 C1 C2 C3 -177.80(10) no C10 C1 C2 C3 3.0(2) no C1 C2 C3 C4 -0.7(3) no C2 C3 C4 C5 -179.5(2) no C2 C3 C4 C9 -0.7(2) no C9 C4 C5 C6 2.0(2) no C3 C4 C5 C6 -179.3(2) no C4 C5 C6 C7 0.1(3) no C5 C6 C7 C8 -1.0(3) no C6 C7 C8 C9 -0.2(3) no C7 C8 C9 C4 2.2(2) no C7 C8 C9 C10 -179.4(2) no C5 C4 C9 C8 -3.0(2) no C3 C4 C9 C8 178.20(10) no C5 C4 C9 C10 178.50(10) no C3 C4 C9 C10 -0.3(2) no O1 C1 C10 C11 -6.2(2) no C2 C1 C10 C11 173.00(10) no O1 C1 C10 C9 176.90(10) no C2 C1 C10 C9 -4.0(2) no C8 C9 C10 C11 7.3(2) no C4 C9 C10 C11 -174.30(10) no C8 C9 C10 C1 -175.70(10) no C4 C9 C10 C1 2.6(2) no C12 N1 C11 C10 -172.80(10) no C1 C10 C11 N1 8.4(2) no C9 C10 C11 N1 -174.70(10) no C11 N1 C12 C15 143.60(10) no C11 N1 C12 C13 -92.8(2) no N1 C12 C13 C14 73.3(2) no C15 C12 C13 C14 -164.6(2) no C12 C13 C14 O2 11.5(3) no C12 C13 C14 O3 -169.3(2) no N1 C12 C15 C20 -114.7(2) no C13 C12 C15 C20 121.9(2) no N1 C12 C15 C16 65.3(2) no C13 C12 C15 C16 -58.1(2) no C20 C15 C16 C17 -0.2(3) no C12 C15 C16 C17 179.8(2) no C15 C16 C17 C18 0.2(3) no C16 C17 C18 C19 -0.2(3) no C17 C18 C19 C20 0.2(3) no C16 C15 C20 C19 0.3(2) no C12 C15 C20 C19 -179.7(2) no C18 C19 C20 C15 -0.3(3) no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag O3 H3o O1 6_565 0.860(10) 1.700(10) 2.547(2) 169(2) yes N1 H1n O1 . 0.860(10) 1.910(10) 2.609(2) 138(2) yes