#------------------------------------------------------------------------------ #$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2208364.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_2208364 loop_ _publ_author_name 'Wang, Shi-Fan' 'Zhou, Li-Jun' 'Yang, Xian' _publ_section_title ; (E)-4-(4-Hydroxy-3-methoxyphenyl)but-3-en-2-one ; _journal_coeditor_code JH6034 _journal_issue 3 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o871 _journal_page_last o872 _journal_volume 62 _journal_year 2006 _chemical_formula_iupac 'C11 H12 O3' _chemical_formula_moiety 'C11 H12 O3' _chemical_formula_sum 'C11 H12 O3' _chemical_formula_weight 192.21 _chemical_name_systematic ; (E)-4-(4-hydroxy-3-methoxyphenyl) but-3-en-2-one ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 97.466(8) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 9.602(5) _cell_length_b 7.780(4) _cell_length_c 13.478(7) _cell_measurement_reflns_used 2995 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 27.85 _cell_measurement_theta_min 2.62 _cell_volume 998.3(9) _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_collection 'SMART (Bruker, 2002)' _computing_data_reduction SAINT _computing_molecular_graphics 'SHELXTL (Sheldrick, 2000)' _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.935 _diffrn_measured_fraction_theta_max 0.955 _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method '\f and \w' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0195 _diffrn_reflns_av_sigmaI/netI 0.0197 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 8188 _diffrn_reflns_theta_full 28.42 _diffrn_reflns_theta_max 28.42 _diffrn_reflns_theta_min 2.14 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_T_max 0.9799 _exptl_absorpt_correction_T_min 0.9674 _exptl_absorpt_correction_type none _exptl_crystal_colour COLOURLESS _exptl_crystal_density_diffrn 1.279 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 408 _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.22 _refine_diff_density_max 0.201 _refine_diff_density_min -0.193 _refine_ls_extinction_coef 0.024(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 131 _refine_ls_number_reflns 2355 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.042 _refine_ls_R_factor_all 0.0587 _refine_ls_R_factor_gt 0.0461 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.07P)^2^+0.1629P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1309 _refine_ls_wR_factor_ref 0.1401 _reflns_number_gt 1816 _reflns_number_total 2355 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file jh6034.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_original_cell_volume 998.2(9) _cod_database_code 2208364 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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 O2 1.20118(12) 0.80293(18) 0.28139(8) 0.0676(4) Uani d . 1 O H2 1.2674 0.7414 0.2716 0.101 Uiso calc R 1 H C4 0.80091(15) 0.82090(19) -0.06027(11) 0.0519(4) Uani d . 1 C H4 0.8317 0.7829 -0.1191 0.062 Uiso calc R 1 H C5 0.90466(13) 0.82078(18) 0.02899(10) 0.0471(3) Uani d . 1 C O3 1.26019(11) 0.64976(17) 0.11386(8) 0.0683(4) Uani d . 1 O C10 1.03328(14) 0.73781(19) 0.02537(10) 0.0494(4) Uani d . 1 C H10 1.0519 0.6873 -0.0340 0.059 Uiso calc R 1 H C8 1.10596(14) 0.80697(19) 0.19783(10) 0.0491(4) Uani d . 1 C C9 1.13266(14) 0.73009(19) 0.10883(10) 0.0481(3) Uani d . 1 C C6 0.88071(15) 0.8990(2) 0.11778(11) 0.0536(4) Uani d . 1 C H6 0.7965 0.9563 0.1212 0.064 Uiso calc R 1 H O1 0.44087(11) 0.88424(18) -0.15226(9) 0.0725(4) Uani d . 1 O C3 0.66655(15) 0.8696(2) -0.06681(12) 0.0539(4) Uani d . 1 C H3 0.6358 0.9171 -0.0102 0.065 Uiso calc R 1 H C2 0.56503(15) 0.8534(2) -0.15629(12) 0.0550(4) Uani d . 1 C C7 0.98065(16) 0.8924(2) 0.20102(11) 0.0564(4) Uani d . 1 C H7 0.9635 0.9462 0.2599 0.068 Uiso calc R 1 H C11 1.31211(18) 0.6130(3) 0.02279(13) 0.0686(5) Uani d . 1 C H11A 1.3154 0.7170 -0.0152 0.103 Uiso calc R 1 H H11B 1.2513 0.5316 -0.0148 0.103 Uiso calc R 1 H H11C 1.4049 0.5656 0.0366 0.103 Uiso calc R 1 H C1 0.61088(19) 0.7969(3) -0.25261(14) 0.0864(7) Uani d . 1 C H1A 0.5309 0.7915 -0.3033 0.130 Uiso calc R 1 H H1B 0.6534 0.6853 -0.2442 0.130 Uiso calc R 1 H H1C 0.6778 0.8775 -0.2724 0.130 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 O2 0.0609(7) 0.0937(9) 0.0452(6) 0.0137(6) -0.0048(5) -0.0031(5) C4 0.0425(7) 0.0572(8) 0.0548(8) -0.0015(6) 0.0020(6) -0.0005(6) C5 0.0383(7) 0.0520(8) 0.0505(7) -0.0029(5) 0.0040(5) 0.0040(6) O3 0.0499(6) 0.1065(10) 0.0471(6) 0.0262(6) 0.0019(5) 0.0004(6) C10 0.0435(7) 0.0595(8) 0.0451(7) 0.0014(6) 0.0049(6) -0.0013(6) C8 0.0462(7) 0.0590(9) 0.0413(7) -0.0010(6) 0.0022(5) 0.0050(6) C9 0.0399(7) 0.0582(8) 0.0466(7) 0.0034(6) 0.0066(5) 0.0053(6) C6 0.0433(7) 0.0621(9) 0.0559(8) 0.0076(6) 0.0085(6) 0.0037(7) O1 0.0396(6) 0.1043(10) 0.0708(8) 0.0046(6) -0.0032(5) -0.0039(6) C3 0.0422(7) 0.0614(9) 0.0568(9) -0.0008(6) 0.0015(6) -0.0009(7) C2 0.0413(8) 0.0594(9) 0.0625(9) -0.0014(6) -0.0004(6) 0.0014(7) C7 0.0564(8) 0.0674(10) 0.0464(8) 0.0073(7) 0.0098(6) -0.0028(7) C11 0.0530(9) 0.0917(13) 0.0630(10) 0.0170(8) 0.0150(7) 0.0022(9) C1 0.0538(10) 0.1337(19) 0.0680(11) 0.0088(11) -0.0059(8) -0.0250(12) 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' O O 0.0106 0.0060 '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 C8 O2 H2 109.5 ? C3 C4 C5 127.19(15) yes C3 C4 H4 116.4 ? C5 C4 H4 116.4 ? C6 C5 C10 118.55(12) yes C6 C5 C4 122.60(13) yes C10 C5 C4 118.85(13) yes C9 O3 C11 117.63(12) yes C9 C10 C5 120.79(13) yes C9 C10 H10 119.6 ? C5 C10 H10 119.6 ? O2 C8 C7 118.81(13) yes O2 C8 C9 121.70(13) yes C7 C8 C9 119.48(13) yes O3 C9 C10 125.48(13) yes O3 C9 C8 114.63(12) yes C10 C9 C8 119.89(13) yes C7 C6 C5 120.63(14) yes C7 C6 H6 119.7 ? C5 C6 H6 119.7 ? C4 C3 C2 124.57(15) yes C4 C3 H3 117.7 ? C2 C3 H3 117.7 ? O1 C2 C3 119.85(15) yes O1 C2 C1 119.74(14) yes C3 C2 C1 120.40(14) yes C6 C7 C8 120.64(14) yes C6 C7 H7 119.7 ? C8 C7 H7 119.7 ? O3 C11 H11A 109.5 ? O3 C11 H11B 109.5 ? H11A C11 H11B 109.5 ? O3 C11 H11C 109.5 ? H11A C11 H11C 109.5 ? H11B C11 H11C 109.5 ? C2 C1 H1A 109.5 ? C2 C1 H1B 109.5 ? H1A C1 H1B 109.5 ? C2 C1 H1C 109.5 ? H1A C1 H1C 109.5 ? H1B C1 H1C 109.5 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O2 C8 1.3556(18) yes O2 H2 0.8200 ? C4 C3 1.336(2) yes C4 C5 1.459(2) yes C4 H4 0.9300 ? C5 C6 1.388(2) yes C5 C10 1.400(2) yes O3 C9 1.3686(17) yes O3 C11 1.413(2) yes C10 C9 1.3785(19) yes C10 H10 0.9300 ? C8 C7 1.380(2) yes C8 C9 1.394(2) yes C6 C7 1.379(2) yes C6 H6 0.9300 ? O1 C2 1.2243(18) yes C3 C2 1.454(2) yes C3 H3 0.9300 ? C2 C1 1.490(2) yes C7 H7 0.9300 ? C11 H11A 0.9600 ? C11 H11B 0.9600 ? C11 H11C 0.9600 ? C1 H1A 0.9600 ? C1 H1B 0.9600 ? C1 H1C 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 O2 H2 O1 4_665 0.82 2.08 2.772(2) 141 yes 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 C3 C4 C5 C6 -10.6(2) C3 C4 C5 C10 169.06(15) C6 C5 C10 C9 1.6(2) C4 C5 C10 C9 -178.04(13) C11 O3 C9 C10 18.5(2) C11 O3 C9 C8 -162.13(15) C5 C10 C9 O3 178.73(14) C5 C10 C9 C8 -0.6(2) O2 C8 C9 O3 0.9(2) C7 C8 C9 O3 179.65(13) O2 C8 C9 C10 -179.69(13) C7 C8 C9 C10 -0.9(2) C10 C5 C6 C7 -1.0(2) C4 C5 C6 C7 178.58(14) C5 C4 C3 C2 -174.64(14) C4 C3 C2 O1 172.18(17) C4 C3 C2 C1 -6.9(3) C5 C6 C7 C8 -0.5(2) O2 C8 C7 C6 -179.72(14) C9 C8 C7 C6 1.5(2)