#------------------------------------------------------------------------------ #$Date: 2013-08-29 18:37:19 +0300 (Thu, 29 Aug 2013) $ #$Revision: 88064 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/20/57/2205753.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_2205753 loop_ _publ_author_name 'Zhang, Yong-Bin' 'Guo, Wei' 'Hao, Jun-Sheng' 'Li, Dong-Hong' 'Huang, Shu-Ping' 'Xia, Chi-Zhong' _publ_section_title ; 3-Acetoxy-4-(4-hydroxyphenethylamino)but-3-en-1-one ; _journal_issue 5 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1318 _journal_page_last o1320 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C14 H17 N O3' _chemical_formula_moiety 'C14 H17 N O3' _chemical_formula_sum 'C14 H17 N O3' _chemical_formula_weight 247.29 _chemical_name_common ; '3-aceto-4-(4-hydroxyphenethylamino)-3-ene-butenone' ; _chemical_name_systematic ; 3-Acetoxy-4-(4-hydroxyphenethylamino)but-3-en-1-one ; _space_group_IT_number 9 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'C -2yc' _symmetry_space_group_name_H-M 'C 1 c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL97 _cell_angle_alpha 90.00 _cell_angle_beta 98.558(4) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.400(2) _cell_length_b 16.462(5) _cell_length_c 10.999(3) _cell_measurement_reflns_used 3626 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 26.76 _cell_measurement_theta_min 2.47 _cell_volume 1325.0(6) _computing_cell_refinement SMART _computing_data_collection 'SMART (Bruker, 2000)' _computing_data_reduction 'SHELXTL (Bruker, 1999)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 298(2) _diffrn_detector_area_resol_mean '100x100 microns' _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _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 0.0226 _diffrn_reflns_av_sigmaI/netI 0.0276 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 3186 _diffrn_reflns_theta_full 25.01 _diffrn_reflns_theta_max 25.01 _diffrn_reflns_theta_min 2.47 _diffrn_standards_decay_% 2.27 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_T_max 0.9828 _exptl_absorpt_correction_T_min 0.9743 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.240 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 528 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.144 _refine_diff_density_min -0.154 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.203 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 166 _refine_ls_number_reflns 1173 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.202 _refine_ls_R_factor_all 0.0508 _refine_ls_R_factor_gt 0.0494 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0436P)^2^+0.4543P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1115 _refine_ls_wR_factor_ref 0.1123 _reflns_number_gt 1134 _reflns_number_total 1173 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file lh6395.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'C c' _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_cell_volume 1324.9(7) _cod_database_code 2205753 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' 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 C9 0.2626(5) 0.0173(2) 0.7758(3) 0.0438(9) Uani d . 1 C H9A 0.2960 0.0403 0.8531 0.053 Uiso calc R 1 H O3 -0.5149(4) 0.37437(19) 0.9299(3) 0.0628(9) Uani d . 1 O H3A -0.6191 0.3764 0.8922 0.094 Uiso calc R 1 H N1 0.1251(4) 0.0510(2) 0.7065(3) 0.0485(8) Uani d . 1 N H1A 0.0926 0.0311 0.6342 0.058 Uiso calc R 1 H C11 0.3084(5) -0.0935(2) 0.6352(4) 0.0446(9) Uani d . 1 C C1 -0.4300(5) 0.3073(2) 0.8957(3) 0.0417(9) Uani d . 1 C O1 0.1809(4) -0.06909(19) 0.5588(3) 0.0589(8) Uani d . 1 O C10 0.3655(5) -0.0488(2) 0.7481(3) 0.0391(8) Uani d . 1 C C3 -0.4078(6) 0.1909(3) 0.7689(4) 0.0537(11) Uani d . 1 C H3B -0.4568 0.1593 0.7021 0.064 Uiso calc R 1 H C5 -0.1770(5) 0.2158(3) 0.9368(3) 0.0461(10) Uani d . 1 C H5A -0.0673 0.2016 0.9848 0.055 Uiso calc R 1 H C4 -0.2443(5) 0.1679(2) 0.8383(3) 0.0428(9) Uani d . 1 C C7 -0.1397(6) 0.0944(3) 0.8038(4) 0.0525(11) Uani d . 1 C H7A -0.2204 0.0603 0.7478 0.079 Uiso calc R 1 H H7B -0.0973 0.0629 0.8770 0.079 Uiso calc R 1 H C2 -0.5004(5) 0.2600(3) 0.7967(4) 0.0504(11) Uani d . 1 C H2A -0.6098 0.2744 0.7486 0.061 Uiso calc R 1 H C8 0.0230(5) 0.1198(2) 0.7430(4) 0.0520(10) Uani d . 1 C H8A -0.0200 0.1523 0.6710 0.078 Uiso calc R 1 H H8B 0.1037 0.1533 0.7997 0.078 Uiso calc R 1 H C13 0.3971(8) -0.1719(3) 0.6085(5) 0.0704(14) Uani d . 1 C H13A 0.3178 -0.2013 0.5466 0.106 Uiso calc R 1 H H13B 0.4195 -0.2039 0.6822 0.106 Uiso calc R 1 H H13C 0.5108 -0.1609 0.5796 0.106 Uiso calc R 1 H O2 0.6439(4) -0.1160(2) 0.8053(3) 0.0736(10) Uani d . 1 O C6 -0.2675(5) 0.2843(3) 0.9663(4) 0.0482(10) Uani d . 1 C H6A -0.2192 0.3153 1.0340 0.058 Uiso calc R 1 H C12 0.5282(5) -0.0697(2) 0.8329(4) 0.0469(9) Uani d . 1 C C14 0.5599(7) -0.0326(3) 0.9600(4) 0.0647(13) Uani d . 1 C H14A 0.6653 -0.0570 1.0074 0.097 Uiso calc R 1 H H14B 0.4548 -0.0419 0.9999 0.097 Uiso calc R 1 H H14C 0.5795 0.0248 0.9535 0.097 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 C9 0.042(2) 0.050(2) 0.040(2) 0.0042(18) 0.0076(17) -0.0025(18) O3 0.0514(19) 0.066(2) 0.066(2) 0.0218(15) -0.0078(15) -0.0148(16) N1 0.0459(18) 0.052(2) 0.0469(19) 0.0203(16) 0.0047(15) 0.0013(15) C11 0.043(2) 0.042(2) 0.050(2) 0.0072(18) 0.0137(18) 0.0066(17) C1 0.038(2) 0.045(2) 0.042(2) 0.0112(18) 0.0061(17) 0.0015(16) O1 0.0584(17) 0.0637(19) 0.0507(17) 0.0188(16) -0.0043(14) -0.0067(14) C10 0.0387(19) 0.037(2) 0.044(2) 0.0078(16) 0.0141(16) 0.0044(16) C3 0.043(2) 0.068(3) 0.047(2) 0.009(2) -0.0021(18) -0.011(2) C5 0.032(2) 0.059(3) 0.045(2) 0.0093(18) -0.0003(17) -0.0009(18) C4 0.0315(19) 0.049(2) 0.049(2) 0.0059(16) 0.0076(17) 0.0036(18) C7 0.047(2) 0.050(3) 0.061(3) 0.0090(19) 0.007(2) 0.001(2) C2 0.037(2) 0.066(3) 0.044(2) 0.0187(19) -0.0055(18) -0.0047(19) C8 0.055(3) 0.044(2) 0.058(3) 0.0161(19) 0.011(2) 0.0029(19) C13 0.076(3) 0.058(3) 0.075(3) 0.017(2) 0.002(3) -0.019(2) O2 0.0539(18) 0.082(2) 0.080(2) 0.0335(17) -0.0040(16) -0.0185(18) C6 0.037(2) 0.061(3) 0.044(2) -0.003(2) -0.0003(16) -0.0121(19) C12 0.042(2) 0.042(2) 0.056(3) 0.0131(19) 0.0064(18) 0.0012(18) C14 0.057(3) 0.088(3) 0.046(2) 0.026(2) -0.001(2) 0.005(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 0.0000 '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' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 N1 C9 C10 127.8(4) y N1 C9 H9A 116.1 ? C10 C9 H9A 116.1 ? C1 O3 H3A 109.5 ? C9 N1 C8 124.4(4) y C9 N1 H1A 117.8 ? C8 N1 H1A 117.8 ? O1 C11 C10 120.9(3) ? O1 C11 C13 117.4(4) ? C10 C11 C13 121.7(4) ? O3 C1 C2 123.1(3) ? O3 C1 C6 117.9(3) ? C2 C1 C6 119.0(3) ? C9 C10 C12 118.3(3) ? C9 C10 C11 119.1(3) ? C12 C10 C11 122.6(3) ? C4 C3 C2 121.6(4) ? C4 C3 H3B 119.2 ? C2 C3 H3B 119.2 ? C4 C5 C6 121.7(3) ? C4 C5 H5A 119.2 ? C6 C5 H5A 119.2 ? C5 C4 C3 117.6(3) ? C5 C4 C7 121.2(3) ? C3 C4 C7 121.2(4) ? C4 C7 C8 111.0(3) ? C4 C7 H7A 109.4 ? C8 C7 H7A 109.4 ? C4 C7 H7B 109.4 ? C8 C7 H7B 109.4 ? H7A C7 H7B 108.0 ? C1 C2 C3 119.8(3) ? C1 C2 H2A 120.1 ? C3 C2 H2A 120.1 ? N1 C8 C7 112.7(3) y N1 C8 H8A 109.0 ? C7 C8 H8A 109.0 ? N1 C8 H8B 109.0 ? C7 C8 H8B 109.0 ? H8A C8 H8B 107.8 ? C11 C13 H13A 109.5 ? C11 C13 H13B 109.5 ? H13A C13 H13B 109.5 ? C11 C13 H13C 109.5 ? H13A C13 H13C 109.5 ? H13B C13 H13C 109.5 ? C5 C6 C1 120.4(4) ? C5 C6 H6A 119.8 ? C1 C6 H6A 119.8 ? O2 C12 C10 122.3(4) ? O2 C12 C14 117.8(4) ? C10 C12 C14 119.9(3) ? C12 C14 H14A 109.5 ? C12 C14 H14B 109.5 ? H14A C14 H14B 109.5 ? C12 C14 H14C 109.5 ? H14A C14 H14C 109.5 ? H14B C14 H14C 109.5 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag C9 N1 1.301(5) y C9 C10 1.388(5) y C9 H9A 0.9300 ? O3 C1 1.352(4) ? O3 H3A 0.8200 ? N1 C8 1.452(5) y N1 H1A 0.8600 ? C11 O1 1.234(5) ? C11 C10 1.451(6) ? C11 C13 1.497(6) ? C1 C2 1.376(5) ? C1 C6 1.384(5) ? C10 C12 1.451(5) ? C3 C4 1.384(5) ? C3 C2 1.384(6) ? C3 H3B 0.9300 ? C5 C4 1.372(5) ? C5 C6 1.374(5) ? C5 H5A 0.9300 ? C4 C7 1.516(5) ? C7 C8 1.520(6) ? C7 H7A 0.9700 ? C7 H7B 0.9700 ? C2 H2A 0.9300 ? C8 H8A 0.9700 ? C8 H8B 0.9700 ? C13 H13A 0.9600 ? C13 H13B 0.9600 ? C13 H13C 0.9600 ? O2 C12 1.218(4) ? C6 H6A 0.9300 ? C12 C14 1.512(6) ? C14 H14A 0.9600 ? C14 H14B 0.9600 ? C14 H14C 0.9600 ? 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 N1 H1A O1 . 0.86 2.00 2.629(4) 129.3 y O3 H3A O2 3_355 0.82 1.87 2.692(4) 178.5 y C9 H9A O1 2 0.93 2.58 3.368(5) 143.2 y 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 C9 N1 C8 C7 -90.7(5) y _cod_database_fobs_code 2205753