#------------------------------------------------------------------------------ #$Date: 2013-08-29 18:37:19 +0300 (Thu, 29 Aug 2013) $ #$Revision: 88064 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/23/04/2230481.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_2230481 loop_ _publ_author_name 'Wang, Jian-Guo' _publ_section_title ; 4-(4-Hydroxyphenyl)butan-2-one ; _journal_coeditor_code SJ5132 _journal_issue 6 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1411 _journal_volume 67 _journal_year 2011 _chemical_formula_iupac 'C10 H12 O2' _chemical_formula_moiety 'C10 H12 O2' _chemical_formula_sum 'C10 H12 O2' _chemical_formula_weight 164.20 _chemical_name_systematic ; 4-(4-Hydroxyphenyl)butan-2-one ; _space_group_IT_number 33 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2c -2n' _symmetry_space_group_name_H-M 'P n a 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 14.0242(13) _cell_length_b 12.4450(12) _cell_length_c 5.2706(5) _cell_measurement_reflns_used 2580 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 24.48 _cell_measurement_theta_min 2.19 _cell_volume 919.88(15) _computing_cell_refinement 'SAINT (Bruker, 1997)' _computing_data_collection 'SMART (Bruker, 1997)' _computing_data_reduction 'SAINT (Bruker, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _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 MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.1005 _diffrn_reflns_av_sigmaI/netI 0.0577 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_number 5687 _diffrn_reflns_theta_full 26.00 _diffrn_reflns_theta_max 26.00 _diffrn_reflns_theta_min 2.19 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.186 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 352 _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.210 _refine_diff_density_min -0.149 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 113 _refine_ls_number_reflns 1797 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.061 _refine_ls_R_factor_all 0.0667 _refine_ls_R_factor_gt 0.0636 _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^)+(0.1055P)^2^+0.0820P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1687 _refine_ls_wR_factor_ref 0.1725 _reflns_number_gt 1678 _reflns_number_total 1797 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file sj5132.cif _[local]_cod_data_source_block I _cod_database_code 2230481 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_type_symbol _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_symmetry_multiplicity _atom_site_disorder_assembly _atom_site_disorder_group C C1 0.38120(16) 0.29404(19) 0.1522(5) 0.0521(6) Uani d . 1 1 . . C C2 0.38140(19) 0.3629(2) 0.3552(6) 0.0627(7) Uani d . 1 1 . . H H2 0.3252 0.3966 0.4048 0.075 Uiso calc R 1 1 . . C C3 0.46513(19) 0.3825(2) 0.4863(5) 0.0622(7) Uani d . 1 1 . . H H3 0.4644 0.4300 0.6224 0.075 Uiso calc R 1 1 . . C C4 0.54959(17) 0.33317(19) 0.4198(5) 0.0532(6) Uani d . 1 1 . . C C5 0.54753(17) 0.2641(2) 0.2135(6) 0.0604(7) Uani d . 1 1 . . H H5 0.6035 0.2298 0.1648 0.072 Uiso calc R 1 1 . . C C6 0.46503(18) 0.2445(2) 0.0779(6) 0.0577(6) Uani d . 1 1 . . H H6 0.4658 0.1987 -0.0614 0.069 Uiso calc R 1 1 . . C C7 0.6424(2) 0.3537(2) 0.5558(5) 0.0639(7) Uani d . 1 1 . . H H7A 0.6750 0.2860 0.5835 0.077 Uiso calc R 1 1 . . H H7B 0.6293 0.3854 0.7203 0.077 Uiso calc R 1 1 . . C C8 0.70702(18) 0.4287(2) 0.4049(5) 0.0573(6) Uani d . 1 1 . . H H8A 0.7130 0.4007 0.2338 0.069 Uiso calc R 1 1 . . H H8B 0.6764 0.4984 0.3933 0.069 Uiso calc R 1 1 . . C C9 0.80525(18) 0.4441(2) 0.5120(5) 0.0622(7) Uani d . 1 1 . . C C10 0.8711(2) 0.5121(3) 0.3595(8) 0.0852(11) Uani d . 1 1 . . H H10A 0.9327 0.5135 0.4389 0.128 Uiso calc R 1 1 . . H H10B 0.8462 0.5839 0.3495 0.128 Uiso calc R 1 1 . . H H10C 0.8768 0.4828 0.1917 0.128 Uiso calc R 1 1 . . O O1 0.29729(13) 0.27805(18) 0.0238(5) 0.0713(6) Uani d . 1 1 . . H H1 0.303(3) 0.230(4) -0.105(10) 0.107 Uiso d . 1 1 . . O O2 0.82901(17) 0.4040(2) 0.7093(5) 0.0906(8) Uani d . 1 1 . . 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 C1 0.0400(11) 0.0505(12) 0.0657(15) -0.0032(9) -0.0021(10) 0.0083(11) C2 0.0480(12) 0.0688(15) 0.0715(16) 0.0096(11) 0.0080(11) 0.0007(13) C3 0.0634(15) 0.0657(14) 0.0576(13) 0.0022(12) 0.0011(12) -0.0075(12) C4 0.0509(12) 0.0542(12) 0.0544(13) -0.0026(10) -0.0061(10) 0.0062(10) C5 0.0419(11) 0.0611(13) 0.0782(17) 0.0042(10) -0.0035(11) -0.0084(13) C6 0.0481(13) 0.0537(13) 0.0714(15) -0.0009(10) -0.0056(11) -0.0101(11) C7 0.0652(16) 0.0635(14) 0.0629(16) -0.0026(13) -0.0180(13) 0.0059(12) C8 0.0547(14) 0.0560(13) 0.0612(14) -0.0002(10) -0.0136(11) -0.0033(12) C9 0.0554(13) 0.0494(12) 0.0818(18) 0.0059(11) -0.0183(14) -0.0129(13) C10 0.0637(18) 0.0765(19) 0.115(3) -0.0186(14) -0.0073(17) -0.014(2) O1 0.0410(9) 0.0783(13) 0.0947(15) -0.0026(8) -0.0109(10) -0.0017(12) O2 0.0806(16) 0.0855(14) 0.1056(18) -0.0036(12) -0.0449(14) 0.0113(14) 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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 C1 O1 . . 118.5(2) ? C2 C1 C6 . . 119.8(2) ? O1 C1 C6 . . 121.6(2) ? C1 C2 C3 . . 120.1(2) ? C1 C2 H2 . . 120.0 ? C3 C2 H2 . . 120.0 ? C4 C3 C2 . . 121.6(2) ? C4 C3 H3 . . 119.2 ? C2 C3 H3 . . 119.2 ? C3 C4 C5 . . 117.2(2) ? C3 C4 C7 . . 123.0(2) ? C5 C4 C7 . . 119.7(2) ? C6 C5 C4 . . 122.2(2) ? C6 C5 H5 . . 118.9 ? C4 C5 H5 . . 118.9 ? C5 C6 C1 . . 119.1(2) ? C5 C6 H6 . . 120.4 ? C1 C6 H6 . . 120.4 ? C4 C7 C8 . . 111.6(2) ? C4 C7 H7A . . 109.3 ? C8 C7 H7A . . 109.3 ? C4 C7 H7B . . 109.3 ? C8 C7 H7B . . 109.3 ? H7A C7 H7B . . 108.0 ? C9 C8 C7 . . 115.3(2) ? C9 C8 H8A . . 108.5 ? C7 C8 H8A . . 108.5 ? C9 C8 H8B . . 108.5 ? C7 C8 H8B . . 108.5 ? H8A C8 H8B . . 107.5 ? O2 C9 C10 . . 122.1(3) ? O2 C9 C8 . . 121.9(3) ? C10 C9 C8 . . 116.0(3) ? C9 C10 H10A . . 109.5 ? C9 C10 H10B . . 109.5 ? H10A C10 H10B . . 109.5 ? C9 C10 H10C . . 109.5 ? H10A C10 H10C . . 109.5 ? H10B C10 H10C . . 109.5 ? C1 O1 H1 . . 113(3) ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 C2 . 1.371(4) ? C1 O1 . 1.372(3) ? C1 C6 . 1.384(4) ? C2 C3 . 1.384(4) ? C2 H2 . 0.9300 ? C3 C4 . 1.379(4) ? C3 H3 . 0.9300 ? C4 C5 . 1.386(4) ? C4 C7 . 1.508(3) ? C5 C6 . 1.382(4) ? C5 H5 . 0.9300 ? C6 H6 . 0.9300 ? C7 C8 . 1.525(4) ? C7 H7A . 0.9700 ? C7 H7B . 0.9700 ? C8 C9 . 1.501(3) ? C8 H8A . 0.9700 ? C8 H8B . 0.9700 ? C9 O2 . 1.200(4) ? C9 C10 . 1.489(5) ? C10 H10A . 0.9600 ? C10 H10B . 0.9600 ? C10 H10C . 0.9600 ? O1 H1 . 0.91(5) ? 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 O1 H1 O2 3_454 0.91(5) 1.97(5) 2.842(4) 161(5) 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag O1 C1 C2 C3 . . . . -178.8(3) ? C6 C1 C2 C3 . . . . -0.3(4) ? C1 C2 C3 C4 . . . . -0.7(4) ? C2 C3 C4 C5 . . . . 0.9(4) ? C2 C3 C4 C7 . . . . 179.1(3) ? C3 C4 C5 C6 . . . . 0.0(4) ? C7 C4 C5 C6 . . . . -178.3(3) ? C4 C5 C6 C1 . . . . -1.0(4) ? C2 C1 C6 C5 . . . . 1.2(4) ? O1 C1 C6 C5 . . . . 179.6(3) ? C3 C4 C7 C8 . . . . -102.6(3) ? C5 C4 C7 C8 . . . . 75.6(3) ? C4 C7 C8 C9 . . . . -173.6(2) ? C7 C8 C9 O2 . . . . -3.5(4) ? C7 C8 C9 C10 . . . . 176.7(2) ? _cod_database_fobs_code 2230481