#------------------------------------------------------------------------------ #$Date: 2023-09-18 14:42:39 +0300 (Mon, 18 Sep 2023) $ #$Revision: 286386 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/31/22/2312288.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_2312288 loop_ _publ_author_name 'Khouchen, Malak' 'Klar, Paul Benjamin' 'Chintakindi, Hrushikesh' 'Suresh, Ashwin' 'Palatinus, Lukas' _publ_section_title ; Optimal estimated standard uncertainties of reflection intensities for kinematical refinement from 3D electron diffraction data ; _journal_coeditor_code PL5027 _journal_issue 5 _journal_name_full 'Acta Crystallographica Section A Foundations and Advances' _journal_page_first 427 _journal_page_last 439 _journal_paper_doi 10.1107/S2053273323005053 _journal_volume 79 _journal_year 2023 _chemical_absolute_configuration rm _chemical_formula_sum 'C13 H18 O2' _chemical_formula_weight 206.3 _chemical_name_common (S)-(+)-Ibuprofen _chemical_name_systematic ; (S)-(+)-Ibuprofen ; _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 1' _symmetry_cell_setting monoclinic _symmetry_Int_Tables_number 4 _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _cell_angle_alpha 90 _cell_angle_beta 112.24(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 12.368(4) _cell_length_b 8.021(3) _cell_length_c 13.536(5) _cell_measurement_reflns_used 3884 _cell_measurement_temperature 95.15 _cell_measurement_theta_max 0.72 _cell_measurement_theta_min 0.06 _cell_volume 1242.9(8) _computing_cell_refinement 'PETS2(ver 2.2.20220612.1425)' _computing_data_collection 'self-written scripts, OLYMPUS iTEM' _computing_data_reduction 'PETS2(ver 2.2.20220612.1425)' _computing_molecular_graphics 'VESTA 3' _computing_structure_refinement 'JANA2020 ' _computing_structure_solution superflip _diffrn_ambient_temperature 95.15 _diffrn_detector 'Hybrid pixel detector ASI Cheetah (side-mounted)' _diffrn_measured_fraction_theta_full 0.85 _diffrn_measured_fraction_theta_max 0.85 _diffrn_measurement_device 'TEM FEI Tecnai G2 20' _diffrn_measurement_method 'continuous-rotation 3D ED' _diffrn_measurement_specimen_support 'holey carbon grid' _diffrn_radiation_probe electron _diffrn_radiation_source 'Lab6 cathode' _diffrn_radiation_type 'electrons 200 keV' _diffrn_radiation_wavelength 0.0251 _diffrn_reflns_av_R_equivalents 0.1658 _diffrn_reflns_av_unetI/netI 0.2013 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 3884 _diffrn_reflns_theta_full 0.72 _diffrn_reflns_theta_max 0.72 _diffrn_reflns_theta_min 0.06 _exptl_crystal_density_diffrn 1.1024 _exptl_crystal_description block _exptl_crystal_F_000 184.42 _refine_diff_density_max 0.27 _refine_diff_density_min -0.26 _refine_ls_extinction_coef 3.7(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2017/1 (Sheldrick, 2015)' _refine_ls_goodness_of_fit_gt 2.2218 _refine_ls_goodness_of_fit_ref 2.0258 _refine_ls_hydrogen_treatment mixed _refine_ls_number_constraints 139 _refine_ls_number_parameters 127 _refine_ls_number_reflns 1212 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.2145 _refine_ls_R_factor_gt 0.1882 _refine_ls_shift/su_max 0.0459 _refine_ls_shift/su_mean 0.0057 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details w=1/(\s^2^(I)+0.0004I^2^) _refine_ls_weighting_scheme sigma _refine_ls_wR_factor_gt 0.4005 _refine_ls_wR_factor_ref 0.4260 _reflns_number_gt 883 _reflns_number_total 1212 _reflns_threshold_expression I>3\s(I) _cod_data_source_file pl5027.cif _cod_data_source_block ibuprofen_model2 _cod_database_code 2312288 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 x,y,z 2 -x,y+1/2,-z loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_adp_type _atom_site_U_iso_or_equiv _atom_site_site_symmetry_multiplicity _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1a O 0.3483(19) 0.520(3) 1.1738(15) Uiso 0.047(5) 2 1 d . . . O2a O 0.230(2) 0.681(3) 1.0468(16) Uiso 0.049(5) 2 1 d . . . H1a H 0.291(9) 0.763(13) 1.080(9) Uiso 0.0977 2 1 d . . . C1a C 0.254(2) 0.544(3) 1.1011(17) Uiso 0.037(5) 2 1 d . . . C2a C 0.155(2) 0.408(3) 1.0677(17) Uiso 0.043(6) 2 1 d . . . H2a H 0.161004 0.313979 1.124761 Uiso 0.0866 2 1 d . . . C3a C 0.1671(16) 0.331(2) 0.9703(13) Uiso 0.020(4) 2 1 d . . . C4a C 0.2346(19) 0.185(3) 0.9830(16) Uiso 0.035(5) 2 1 d . . . H4a H 0.279552 0.136015 1.060603 Uiso 0.0709 2 1 d . . . C5a C 0.2434(16) 0.101(2) 0.8919(12) Uiso 0.022(4) 2 1 d . . . H5a H 0.309796 0.010112 0.904912 Uiso 0.0435 2 1 d . . . C6a C 0.1708(15) 0.1332 0.7919(12) Uiso 0.009(4) 2 1 d . . . C7a C 0.0949(19) 0.276(3) 0.7758(17) Uiso 0.032(5) 2 1 d . . . H7a H 0.044494 0.314088 0.696613 Uiso 0.0631 2 1 d . . . C8a C 0.0853(18) 0.365(3) 0.8575(13) Uiso 0.031(5) 2 1 d . . . H8a H 0.020032 0.457851 0.841836 Uiso 0.0622 2 1 d . . . C9a C 0.1710(16) 0.036(2) 0.6962(12) Uiso 0.020(4) 2 1 d . . . H9a1 H 0.172883 0.120675 0.636497 Uiso 0.0407 2 1 d . . . H9a2 H 0.247725 -0.037318 0.718552 Uiso 0.0407 2 1 d . . . C10a C 0.0560(17) -0.084(3) 0.6472(13) Uiso 0.029(5) 2 1 d . . . H10a H -0.024033 -0.02508 0.637934 Uiso 0.0576 2 1 d . . . C11a C 0.062(2) -0.139(3) 0.5431(16) Uiso 0.042(5) 2 1 d . . . H11a H 0.082053 -0.035243 0.504681 Uiso 0.0844 2 1 d . . . H11b H 0.127539 -0.231109 0.557875 Uiso 0.0844 2 1 d . . . H11c H -0.019944 -0.189306 0.493457 Uiso 0.0844 2 1 d . . . C12a C 0.067(2) -0.229(3) 0.7203(17) Uiso 0.042(5) 2 1 d . . . H12a H 0.003048 -0.319715 0.680316 Uiso 0.0846 2 1 d . . . H12b H 0.151229 -0.281542 0.74315 Uiso 0.0846 2 1 d . . . H12c H 0.053418 -0.187212 0.789239 Uiso 0.0846 2 1 d . . . C13a C 0.037(3) 0.487(4) 1.053(2) Uiso 0.067(7) 2 1 d . . . H13a H -0.02582 0.391412 1.041545 Uiso 0.1349 2 1 d . . . H13b H 0.045482 0.557643 1.121102 Uiso 0.1349 2 1 d . . . H13c H 0.010264 0.565243 0.984649 Uiso 0.1349 2 1 d . . . O2b O 0.541(2) -0.289(3) 0.2291(17) Uiso 0.055(5) 2 1 d . . . O1b O 0.413(2) -0.124(3) 0.1015(16) Uiso 0.051(5) 2 1 d . . . H1b H 0.475(8) -0.366(14) 0.205(10) Uiso 0.111 2 1 d . . . C1b C 0.512(2) -0.146(3) 0.1738(16) Uiso 0.035(5) 2 1 d . . . C2b C 0.611(2) -0.023(3) 0.1959(16) Uiso 0.046(6) 2 1 d . . . H2b H 0.691943 -0.083435 0.211316 Uiso 0.0914 2 1 d . . . C3b C 0.611(2) 0.073(3) 0.2907(16) Uiso 0.039(5) 2 1 d . . . C4b C 0.6879(18) 0.008(3) 0.3981(14) Uiso 0.036(5) 2 1 d . . . H4b H 0.744922 -0.094793 0.406557 Uiso 0.0713 2 1 d . . . C5b C 0.6804(19) 0.088(3) 0.4849(17) Uiso 0.039(5) 2 1 d . . . H5b H 0.726041 0.031082 0.559793 Uiso 0.0784 2 1 d . . . C6b C 0.6217(19) 0.233(3) 0.4882(15) Uiso 0.030(5) 2 1 d . . . C7b C 0.550(2) 0.298(3) 0.3855(16) Uiso 0.045(6) 2 1 d . . . H7b H 0.500624 0.409417 0.377044 Uiso 0.0904 2 1 d . . . C8b C 0.5479(18) 0.202(2) 0.2937(15) Uiso 0.027(5) 2 1 d . . . H8b H 0.486875 0.242141 0.218764 Uiso 0.0543 2 1 d . . . C9b C 0.6377(19) 0.321(3) 0.5875(15) Uiso 0.043(5) 2 1 d . . . H9b1 H 0.646674 0.232646 0.648523 Uiso 0.0864 2 1 d . . . H9b2 H 0.5577 0.376672 0.581319 Uiso 0.0864 2 1 d . . . C10b C 0.731(2) 0.443(3) 0.6263(15) Uiso 0.043(6) 2 1 d . . . H10b H 0.801633 0.365674 0.628986 Uiso 0.0867 2 1 d . . . C11b C 0.756(2) 0.519(3) 0.7400(18) Uiso 0.057(6) 2 1 d . . . H11d H 0.813729 0.439941 0.799233 Uiso 0.1131 2 1 d . . . H11e H 0.676206 0.529633 0.752029 Uiso 0.1131 2 1 d . . . H11f H 0.794042 0.638607 0.745324 Uiso 0.1131 2 1 d . . . C12b C 0.7173(19) 0.601(3) 0.5498(14) Uiso 0.039(5) 2 1 d . . . H12d H 0.79347 0.675931 0.580418 Uiso 0.0777 2 1 d . . . H12e H 0.705614 0.559546 0.472097 Uiso 0.0777 2 1 d . . . H12f H 0.643753 0.672268 0.546386 Uiso 0.0777 2 1 d . . . C13b C 0.598(2) 0.086(3) 0.1012(15) Uiso 0.041(5) 2 1 d . . . H13d H 0.50821 0.110426 0.057355 Uiso 0.0812 2 1 d . . . H13e H 0.642607 0.200281 0.128271 Uiso 0.0812 2 1 d . . . H13f H 0.634012 0.024541 0.05143 Uiso 0.0812 2 1 d . . . loop_ _atom_type_symbol _atom_type_scat_source C International_Tables_Vol_C H International_Tables_Vol_C O International_Tables_Vol_C 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_2 _geom_angle_site_symmetry_3 _geom_angle H1a O2a C1a . . . 110(6) O1a C1a O2a . . . 123(2) O1a C1a C2a . . . 121(2) O2a C1a C2a . . . 115.9(18) C1a C2a H2a . . . 116.64 C1a C2a C3a . . . 102(2) C1a C2a C13a . . . 111(2) H2a C2a C3a . . . 109.9 H2a C2a C13a . . . 101.28 C3a C2a C13a . . . 117.2(17) C2a C3a C4a . . . 118.8(16) C2a C3a C8a . . . 124.0(18) C4a C3a C8a . . . 114.5(17) C3a C4a H4a . . . 119.48 C3a C4a C5a . . . 121.0(17) H4a C4a C5a . . . 119.48 C4a C5a H5a . . . 118.84 C4a C5a C6a . . . 122.3(18) H5a C5a C6a . . . 118.84 C5a C6a C7a . . . 117.1(16) C5a C6a C9a . . . 123.4(14) C7a C6a C9a . . . 119.4(14) C6a C7a H7a . . . 118.49 C6a C7a C8a . . . 123.0(17) H7a C7a C8a . . . 118.49 C3a C8a C7a . . . 120.0(19) C3a C8a H8a . . . 119.99 C7a C8a H8a . . . 119.99 C6a C9a H9a1 . . . 109.47 C6a C9a H9a2 . . . 109.47 C6a C9a C10a . . . 111.5(16) H9a1 C9a H9a2 . . . 107.37 H9a1 C9a C10a . . . 109.47 H9a2 C9a C10a . . . 109.47 C9a C10a H10a . . . 114.54 C9a C10a C11a . . . 102.1(17) C9a C10a C12a . . . 110.1(13) H10a C10a C11a . . . 113.14 H10a C10a C12a . . . 105.58 C11a C10a C12a . . . 111.6(18) C10a C11a H11a . . . 109.47 C10a C11a H11b . . . 109.47 C10a C11a H11c . . . 109.47 H11a C11a H11b . . . 109.47 H11a C11a H11c . . . 109.47 H11b C11a H11c . . . 109.47 C10a C12a H12a . . . 109.47 C10a C12a H12b . . . 109.47 C10a C12a H12c . . . 109.47 H12a C12a H12b . . . 109.47 H12a C12a H12c . . . 109.47 H12b C12a H12c . . . 109.47 C2a C13a H13a . . . 109.47 C2a C13a H13b . . . 109.47 C2a C13a H13c . . . 109.47 H13a C13a H13b . . . 109.47 H13a C13a H13c . . . 109.47 H13b C13a H13c . . . 109.47 H1b O2b C1b . . . 110(6) O2b C1b O1b . . . 122(2) O2b C1b C2b . . . 115.0(19) O1b C1b C2b . . . 123(2) C1b C2b H2b . . . 111.99 C1b C2b C3b . . . 104(2) C1b C2b C13b . . . 113.2(16) H2b C2b C3b . . . 112 H2b C2b C13b . . . 102.72 C3b C2b C13b . . . 113.2(19) C2b C3b C4b . . . 116.2(19) C2b C3b C8b . . . 129.0(18) C4b C3b C8b . . . 115(2) C3b C4b H4b . . . 122 C3b C4b C5b . . . 116(2) H4b C4b C5b . . . 122 C4b C5b H5b . . . 115.45 C4b C5b C6b . . . 129.1(19) H5b C5b C6b . . . 115.45 C5b C6b C7b . . . 115(2) C5b C6b C9b . . . 123.0(17) C7b C6b C9b . . . 122(2) C6b C7b H7b . . . 122.07 C6b C7b C8b . . . 116(2) H7b C7b C8b . . . 122.07 C3b C8b C7b . . . 129.1(18) C3b C8b H8b . . . 115.45 C7b C8b H8b . . . 115.45 C6b C9b H9b1 . . . 109.47 C6b C9b H9b2 . . . 109.47 C6b C9b C10b . . . 118(2) H9b1 C9b H9b2 . . . 99.43 H9b1 C9b C10b . . . 109.47 H9b2 C9b C10b . . . 109.47 C9b C10b H10b . . . 98.56 C9b C10b C11b . . . 117(2) C9b C10b C12b . . . 115.1(15) H10b C10b C11b . . . 109.93 H10b C10b C12b . . . 111.66 C11b C10b C12b . . . 105.0(17) C10b C11b H11d . . . 109.47 C10b C11b H11e . . . 109.47 C10b C11b H11f . . . 109.47 H11d C11b H11e . . . 109.47 H11d C11b H11f . . . 109.47 H11e C11b H11f . . . 109.47 C10b C12b H12d . . . 109.47 C10b C12b H12e . . . 109.47 C10b C12b H12f . . . 109.47 H12d C12b H12e . . . 109.47 H12d C12b H12f . . . 109.47 H12e C12b H12f . . . 109.47 C2b C13b H13d . . . 109.47 C2b C13b H13e . . . 109.47 C2b C13b H13f . . . 109.47 H13d C13b H13e . . . 109.47 H13d C13b H13f . . . 109.47 H13e C13b H13f . . . 109.47 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance O1a C1a . . 1.22(3) O2a H1a . . 0.98(10) O2a C1a . . 1.29(3) C1a C2a . . 1.58(3) C2a H2a . . 1.06 C2a C3a . . 1.52(3) C2a C13a . . 1.53(4) C3a C4a . . 1.41(3) C3a C8a . . 1.50(2) C4a H4a . . 1.06 C4a C5a . . 1.45(3) C5a H5a . . 1.06 C5a C6a . . 1.34(2) C6a C7a . . 1.45(2) C6a C9a . . 1.51(2) C7a H7a . . 1.06 C7a C8a . . 1.36(3) C8a H8a . . 1.06 C9a H9a1 . . 1.06 C9a H9a2 . . 1.06 C9a C10a . . 1.64(3) C10a H10a . . 1.06 C10a C11a . . 1.50(3) C10a C12a . . 1.50(3) C11a H11a . . 1.06 C11a H11b . . 1.06 C11a H11c . . 1.06 C12a H12a . . 1.06 C12a H12b . . 1.06 C12a H12c . . 1.06 C13a H13a . . 1.06 C13a H13b . . 1.06 C13a H13c . . 1.06 O2b H1b . . 0.98(10) O2b C1b . . 1.34(3) O1b C1b . . 1.26(3) C1b C2b . . 1.51(3) C2b H2b . . 1.06 C2b C3b . . 1.50(3) C2b C13b . . 1.51(3) C3b C4b . . 1.50(3) C3b C8b . . 1.30(3) C4b H4b . . 1.06 C4b C5b . . 1.37(3) C5b H5b . . 1.06 C5b C6b . . 1.38(3) C6b C7b . . 1.44(3) C6b C9b . . 1.46(3) C7b H7b . . 1.06 C7b C8b . . 1.46(3) C8b H8b . . 1.06 C9b H9b1 . . 1.06 C9b H9b2 . . 1.06 C9b C10b . . 1.45(3) C10b H10b . . 1.06 C10b C11b . . 1.57(3) C10b C12b . . 1.61(3) C11b H11d . . 1.06 C11b H11e . . 1.06 C11b H11f . . 1.06 C12b H12d . . 1.06 C12b H12e . . 1.06 C12b H12f . . 1.06 C13b H13d . . 1.06 C13b H13e . . 1.06 C13b H13f . . 1.06 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA O2a H1a O1b . . 1_566 0.98(10) 1.68(11) 2.62(3) 158(12) O2b H1b O1a . . 1_544 0.98(10) 1.72(10) 2.69(3) 170(12) loop_ _restr_distance_atom_site_label_1 _restr_distance_site_symmetry_1 _restr_distance_atom_site_label_2 _restr_distance_site_symmetry_2 _restr_distance_target _restr_distance_target_weight_param O2a . H1a . 0.98 0.001 O2b . H1b . 0.98 0.001 loop_ _restr_equal_angle_atom_site_label_1 _restr_equal_angle_site_symmetry_1 _restr_equal_angle_atom_site_label_2 _restr_equal_angle_site_symmetry_2 _restr_equal_angle_atom_site_label_3 _restr_equal_angle_site_symmetry_3 _restr_equal_angle_class_class_id _restr_equal_angle_class_target_weight_param C1b . O2b . H1b . 1 0.01 C1a . O2a . H1a . 1 0.01