#------------------------------------------------------------------------------ #$Date: 2011-09-28 15:24:46 +0100 (Wed, 28 Sep 2011) $ #$Revision: 26848 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/24/2202426.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_2202426 _journal_name_full 'Acta Crystallographica, Section E' _journal_year 2003 _journal_volume 59 _journal_page_first o1357 _journal_page_last o1358 _publ_section_title ; Redetermination and H-atom refinement of (S)-(+)-ibuprofen ; _space_group_IT_number 4 _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _[local]_cod_cif_authors_sg_H-M 'P 21' loop_ _publ_author_name 'Hansen, Lars Kr.' 'Perlovich, German L.' 'Bauer-Brandl, Annette' _chemical_formula_moiety 'C13 H18 O2' _chemical_formula_sum 'C13 H18 O2' _chemical_formula_iupac 'C13 H18 O2' _chemical_formula_weight 206.27 _symmetry_cell_setting monoclinic loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 12.456(4) _cell_length_b 8.0362(11) _cell_length_c 13.533(3) _cell_angle_alpha 90.00 _cell_angle_beta 112.86(2) _cell_angle_gamma 90.00 _cell_volume 1248.2(5) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _exptl_crystal_density_diffrn 1.098 _diffrn_ambient_temperature 298(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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol C4B 0.8401(2) 0.3199(3) 0.0314(2) 0.0497(7) Uani d . 1 . . C O2A 0.58499(19) -0.2352(3) -0.10390(18) 0.0757(6) Uani d . 1 . . O O1A 0.4640(2) -0.0661(4) -0.2241(2) 0.0890(8) Uani d . 1 . . O O1B 0.7685(2) -0.0391(3) -0.04780(18) 0.0710(6) Uani d . 1 . . O O2B 0.6486(2) 0.1313(3) -0.16958(17) 0.0840(7) Uani d . 1 . . O C7B 0.8336(2) 0.4998(3) 0.2083(2) 0.0493(7) Uani d . 1 . . C C9B 0.7668(2) 0.4546(4) 0.0175(2) 0.0547(7) Uani d . 1 . . C C6B 0.9054(3) 0.3626(4) 0.2220(2) 0.0604(8) Uani d . 1 . . C C8B 0.7632(2) 0.5422(4) 0.1041(2) 0.0548(7) Uani d . 1 . . C C2B 0.8429(3) 0.2278(4) -0.0655(2) 0.0590(8) Uani d . 1 . . C C5B 0.9085(3) 0.2746(4) 0.1358(2) 0.0599(8) Uani d . 1 . . C C10B 0.8355(3) 0.5965(4) 0.3034(2) 0.0614(8) Uani d . 1 . . C C11B 0.9402(3) 0.7128(5) 0.3508(2) 0.0688(9) Uani d . 1 . . C C1B 0.7446(3) 0.1014(4) -0.0998(2) 0.0547(7) Uani d . 1 . . C C12B 0.9347(5) 0.8545(7) 0.2759(4) 0.1068(17) Uani d . 1 . . C C3B 0.9591(3) 0.1463(6) -0.0477(4) 0.0835(11) Uani d . 1 . . C C13B 0.9486(6) 0.7781(7) 0.4595(4) 0.1045(15) Uani d . 1 . . C H3B3 0.990(3) 0.047(6) 0.017(3) 0.117(14) Uiso d . 1 . . H H133 0.170(5) -0.953(8) -0.765(4) 0.16(2) Uiso d . 1 . . H H123 0.363(5) -1.006(10) -0.537(4) 0.19(3) Uiso d . 1 . . H H1BO 0.688(4) -0.106(6) -0.077(3) 0.113(13) Uiso d . 1 . . H H132 0.225(4) -0.765(7) -0.783(4) 0.129(18) Uiso d . 1 . . H H131 0.328(4) -0.925(7) -0.732(4) 0.16(2) Uiso d . 1 . . H H126 0.865(6) 0.933(12) 0.286(6) 0.24(4) Uiso d . 1 . . H H3B2 0.949(2) 0.094(4) -0.118(2) 0.072(9) Uiso d . 1 . . H H2B 0.821(2) 0.309(4) -0.128(2) 0.064(8) Uiso d . 1 . . H H3B1 1.020(4) 0.236(8) -0.031(4) 0.144(18) Uiso d . 1 . . H H125 0.913(4) 0.826(6) 0.200(4) 0.114(14) Uiso d . 1 . . H H124 1.015(5) 0.917(9) 0.310(4) 0.16(2) Uiso d . 1 . . H H103 0.840(2) 0.513(4) 0.360(2) 0.068(9) Uiso d . 1 . . H H104 0.761(3) 0.665(4) 0.279(2) 0.065(9) Uiso d . 1 . . H H6B 0.957(3) 0.326(4) 0.298(3) 0.075(10) Uiso d . 1 . . H H136 0.883(4) 0.850(7) 0.435(4) 0.14(2) Uiso d . 1 . . H H8B 0.712(3) 0.632(5) 0.093(2) 0.073(9) Uiso d . 1 . . H H134 1.009(3) 0.841(5) 0.486(3) 0.074(11) Uiso d . 1 . . H H5B 0.966(2) 0.183(4) 0.152(2) 0.071(9) Uiso d . 1 . . H H9B 0.712(3) 0.480(5) -0.053(3) 0.093(11) Uiso d . 1 . . H H135 0.949(5) 0.679(10) 0.516(5) 0.19(3) Uiso d . 1 . . H H11B 1.020(3) 0.655(4) 0.3544(19) 0.065(8) Uiso d . 1 . . H H3A3 0.332(3) -0.522(6) -0.127(3) 0.108(12) Uiso d . 1 . . H H11A 0.195(4) -0.741(6) -0.642(3) 0.111(14) Uiso d . 1 . . H H101 0.434(3) -0.741(5) -0.577(3) 0.088(12) Uiso d . 1 . . H H3A2 0.403(3) -0.385(6) -0.050(3) 0.104(14) Uiso d . 1 . . H H102 0.348(3) -0.600(6) -0.645(3) 0.115(15) Uiso d . 1 . . H H121 0.298(3) -0.904(6) -0.474(3) 0.108(12) Uiso d . 1 . . H H122 0.210(4) -1.024(7) -0.584(3) 0.122(14) Uiso d . 1 . . H H6A 0.257(3) -0.404(6) -0.563(3) 0.105(12) Uiso d . 1 . . H H2A 0.326(3) -0.265(5) -0.217(3) 0.096(12) Uiso d . 1 . . H H8A 0.500(3) -0.738(5) -0.376(2) 0.074(9) Uiso d . 1 . . H H9A 0.500(3) -0.598(4) -0.227(3) 0.058(8) Uiso d . 1 . . H H5A 0.271(3) -0.283(5) -0.398(2) 0.074(10) Uiso d . 1 . . H H1AO 0.533(4) -0.007(8) -0.208(4) 0.16(2) Uiso d . 1 . . H H3A1 0.481(4) -0.502(6) -0.073(3) 0.131(16) Uiso d . 1 . . H C1A 0.4879(3) -0.2052(4) -0.1705(2) 0.0613(8) Uani d . 1 . . C C2A 0.3900(3) -0.3274(4) -0.1995(3) 0.0680(9) Uani d . 1 . . C C3A 0.4028(4) -0.4412(7) -0.1044(4) 0.0899(13) Uani d . 1 . . C C4A 0.3837(2) -0.4215(4) -0.2990(2) 0.0592(8) Uani d . 1 . . C C5A 0.3135(3) -0.3645(5) -0.4000(3) 0.0776(10) Uani d . 1 . . C C6A 0.3095(3) -0.4468(5) -0.4913(3) 0.0795(10) Uani d . 1 . . C C7A 0.3752(3) -0.5870(4) -0.4856(3) 0.0666(9) Uani d . 1 . . C C8A 0.4460(3) -0.6415(5) -0.3850(3) 0.0685(9) Uani d . 1 . . C C9A 0.4501(3) -0.5605(4) -0.2941(3) 0.0659(9) Uani d . 1 . . C C10A 0.3649(4) -0.6796(6) -0.5864(3) 0.0820(12) Uani d . 1 . . C C11A 0.2651(3) -0.8032(5) -0.6258(3) 0.0756(10) Uani d . 1 . . C C13A 0.2856(5) -0.9476(6) -0.5496(4) 0.0920(13) Uani d . 1 . . C C12A 0.2441(5) -0.8664(9) -0.7376(3) 0.1028(14) Uani d . 1 . . C 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 C4B 0.0532(14) 0.0418(16) 0.0556(16) -0.0049(13) 0.0229(12) -0.0050(13) O2A 0.0602(12) 0.0611(14) 0.0891(14) -0.0027(11) 0.0106(11) 0.0094(12) O1A 0.0719(16) 0.0732(17) 0.0998(18) 0.0059(14) 0.0094(14) 0.0200(15) O1B 0.0699(14) 0.0505(13) 0.0825(14) 0.0005(11) 0.0186(11) 0.0060(12) O2B 0.0822(14) 0.0658(15) 0.0799(14) -0.0034(13) 0.0051(13) 0.0127(13) C7B 0.0488(14) 0.0476(16) 0.0541(16) -0.0070(13) 0.0227(12) -0.0038(14) C9B 0.0545(16) 0.0519(17) 0.0523(16) 0.0047(15) 0.0148(13) 0.0004(14) C6B 0.0727(19) 0.0566(18) 0.0504(17) 0.0013(17) 0.0224(15) 0.0047(16) C8B 0.0554(16) 0.0487(16) 0.0566(16) 0.0090(15) 0.0178(13) 0.0005(14) C2B 0.0716(19) 0.0511(19) 0.0646(18) -0.0018(16) 0.0379(15) -0.0023(16) C5B 0.0644(17) 0.0454(17) 0.0676(19) 0.0142(15) 0.0231(15) 0.0061(15) C10B 0.0675(19) 0.064(2) 0.0547(16) -0.0061(17) 0.0259(14) -0.0025(17) C11B 0.075(2) 0.065(2) 0.0639(19) -0.0088(18) 0.0246(16) -0.0154(17) C1B 0.0708(18) 0.0455(17) 0.0530(16) 0.0069(15) 0.0296(15) -0.0022(14) C12B 0.137(4) 0.098(4) 0.086(3) -0.047(3) 0.043(3) -0.009(3) C3B 0.079(2) 0.080(3) 0.111(3) -0.006(2) 0.058(2) -0.028(3) C13B 0.134(4) 0.093(3) 0.077(3) -0.022(4) 0.030(3) -0.030(3) C1A 0.0580(18) 0.059(2) 0.0647(18) 0.0051(16) 0.0210(16) -0.0113(18) C2A 0.0517(17) 0.069(2) 0.084(2) 0.0060(17) 0.0268(16) -0.0114(19) C3A 0.096(3) 0.105(3) 0.085(3) -0.027(3) 0.053(2) -0.014(3) C4A 0.0421(14) 0.059(2) 0.0703(19) -0.0021(14) 0.0149(13) -0.0007(16) C5A 0.076(2) 0.059(2) 0.087(3) 0.014(2) 0.0197(19) -0.003(2) C6A 0.088(2) 0.069(2) 0.064(2) 0.002(2) 0.0107(18) 0.006(2) C7A 0.0706(19) 0.063(2) 0.069(2) -0.0111(17) 0.0302(16) -0.0028(18) C8A 0.0582(18) 0.068(2) 0.073(2) 0.0080(18) 0.0184(16) -0.0084(19) C9A 0.0570(17) 0.065(2) 0.0634(19) 0.0084(17) 0.0098(15) -0.0041(18) C10A 0.089(3) 0.093(3) 0.071(2) -0.017(2) 0.038(2) -0.006(2) C11A 0.073(2) 0.086(3) 0.0643(19) 0.000(2) 0.0234(16) -0.007(2) C13A 0.106(3) 0.084(3) 0.084(3) -0.013(3) 0.036(3) -0.003(2) C12A 0.105(3) 0.126(4) 0.073(2) -0.010(3) 0.030(2) -0.022(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 C4B C9B . 1.382(4) ? C4B C5B . 1.385(4) ? C4B C2B . 1.517(4) ? O2A C1A . 1.219(3) ? O1A C1A . 1.302(4) ? O1A H1AO . 0.94(6) ? O1B C1B . 1.302(4) ? O1B H1BO . 1.07(5) ? O2B C1B . 1.226(3) ? C7B C8B . 1.383(4) ? C7B C6B . 1.386(4) ? C7B C10B . 1.495(4) ? C9B C8B . 1.382(4) ? C9B H9B . 0.96(3) ? C6B C5B . 1.378(4) ? C6B H6B . 1.03(4) ? C8B H8B . 0.93(4) ? C2B C1B . 1.518(4) ? C2B C3B . 1.521(5) ? C2B H2B . 1.01(3) ? C5B H5B . 0.99(3) ? C10B C11B . 1.529(4) ? C10B H103 . 1.00(3) ? C10B H104 . 1.01(3) ? C11B C12B . 1.508(6) ? C11B C13B . 1.526(5) ? C11B H11B . 1.08(3) ? C12B H126 . 1.12(8) ? C12B H125 . 0.98(4) ? C12B H124 . 1.05(6) ? C3B H3B3 . 1.14(5) ? C3B H3B2 . 1.00(3) ? C3B H3B1 . 1.00(6) ? C13B H136 . 0.95(5) ? C13B H134 . 0.86(4) ? C13B H135 . 1.10(7) ? C1A C2A . 1.496(5) ? C2A C4A . 1.519(4) ? C2A C3A . 1.536(6) ? C2A H2A . 0.89(4) ? C3A H3A3 . 1.05(4) ? C3A H3A2 . 0.87(4) ? C3A H3A1 . 1.03(5) ? C4A C9A . 1.377(4) ? C4A C5A . 1.384(4) ? C5A C6A . 1.385(5) ? C5A H5A . 0.85(4) ? C6A C7A . 1.376(5) ? C6A H6A . 1.00(4) ? C7A C8A . 1.375(4) ? C7A C10A . 1.515(5) ? C8A C9A . 1.374(4) ? C8A H8A . 1.00(4) ? C9A H9A . 0.93(3) ? C10A C11A . 1.516(6) ? C10A H101 . 0.95(4) ? C10A H102 . 0.97(5) ? C11A C13A . 1.506(6) ? C11A C12A . 1.520(5) ? C11A H11A . 0.95(4) ? C13A H123 . 1.03(6) ? C13A H121 . 1.04(4) ? C13A H122 . 1.06(5) ? C12A H133 . 1.09(6) ? C12A H132 . 0.99(6) ? C12A H131 . 1.12(5) ? _cod_database_code 2202426