############################################################################## # # # This CIF contains the data in a paper accepted for publication in # # Acta Crystallographica Section E. It conforms to the requirements of # # Notes for Authors for Acta Crystallographica Section E, and has been # # peer reviewed under the auspices of the IUCr Commission on Journals. # # # # Full details of the Crystallographic Information File format # # are given in the paper "The Crystallographic Information File (CIF): # # a New Standard Archive File for Crystallography" by S. R. Hall, F. H. # # Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685]. # # # # The current version of the core CIF dictionary is obtainable from # # ftp://ftp.iucr.org/pub/cif_core.dic. # # # # Software is freely available for graphical display of the structure(s) # # in this CIF. For information consult the CIF software page # # http://www.iucr.org/resources/cif/software. # # # # This file may be used for bona fide research purposes within the # # scientific community so long as proper attribution is given to the journal # # article from which it was obtained. # # # ############################################################################## data_I _audit_creation_method ; Olex2 1.2 (compiled 2018.04.18 svn.r3501 for OlexSys, GUI svn.r5488) ; _journal_date_recd_electronic 2018-07-10 _journal_date_accepted 2018-08-16 _journal_name_full 'Acta Crystallographica, Section E' _journal_year 2018 _journal_volume 74 _journal_issue 9 _journal_page_first 1319 _journal_page_last 1321 _journal_paper_category GO _journal_paper_doi 10.1107/S2056989018011647 _journal_coeditor_code IS5498 _publ_contact_author_name 'Isid/'orio, Raquel Geralda' _publ_contact_author_address ; Avenida Ant\^onio Carlos, 6627, Belo Horizonte Minas Gerais, CEP 31.270-90, Brazil ; _publ_contact_author_email 'raquelgeisi@hotmail.com' _publ_contact_author_phone '+553134096973' _publ_section_title ; Crystal structure of 2-hydroxy-3-(prop-2-yn-1-yl)naphthalene-1,4-dione ; _publ_section_title_footnote . loop_ _publ_author_name _publ_author_footnote _publ_author_address 'Raquel Geralda, Isid\'orio' . ; Departamento de Produtos Farmac\^euticos Faculdade de Farm\'acia Universidade Federal de Minas Gerais Avenida Ant\^onio Carlos, 6627 Belo Horizonte Minas Gerais CEP 31.270-901 Brazil ; 'Flaviano Melo, Ottoni' . ; Departamento de Produtos Farmac\^euticos Faculdade de Farm\'acia Universidade Federal de Minas Gerais Avenida Ant\^onio Carlos, 6627 Belo Horizonte Minas Gerais CEP 31.270-901 Brazil ; 'Ricardo Jos\'e, Alves' . ; Departamento de Produtos Farmac\^euticos Faculdade de Farm\'acia Universidade Federal de Minas Gerais Avenida Ant\^onio Carlos, 6627 Belo Horizonte Minas Gerais CEP 31.270-901 Brazil ; 'Nivaldo L\'ucio, Speziali' . ; Departamento de F\'isica Instituto de Ci\^encias Exatas Universidade Federal de Minas Gerais Avenida Ant\^onio Carlos, 6627 Belo Horizonte Minas Gerais CEP 31.270-901, Brazil ; _publ_section_synopsis ; The naphthoquinone unit in 2-hydroxy-3-(prop-2-yn-1-yl)naphthalene-1,4-dione is essentially planar and the linear propargyl group is nearly perpendicular to the naphthalene ring system. In the crystal, O---H...O and C---H...O hydrogen bonds form an infinite tape structure. ; _chemical_name_systematic ; 2-Hydroxy-3-(prop-2-yn-1-yl)naphthalene-1,4-dione ; _chemical_name_common ' C-propargyl lawsone' _chemical_formula_moiety 'C13 H8 O3' _chemical_formula_sum 'C13 H8 O3' _chemical_formula_iupac 'C13 H8 O3' _chemical_formula_weight 212.19 _chemical_melting_point ? _chemical_melting_point_gt 396.8 _chemical_melting_point_lt 397.5 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _space_group_crystal_system triclinic _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.3695(4) _cell_length_b 9.5278(8) _cell_length_c 10.2972(9) _cell_angle_alpha 96.814(7) _cell_angle_beta 93.432(7) _cell_angle_gamma 102.977(7) _cell_volume 507.68(8) _cell_formula_units_Z 2 _cell_measurement_reflns_used 1721 _cell_measurement_theta_min 3.1570 _cell_measurement_theta_max 28.6890 _cell_measurement_temperature 293(2) _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.388 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_F_000 220 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; (CrysAlis PRO; Rigaku OD, 2015) ; _shelx_estimated_absorpt_T_min ? _shelx_estimated_absorpt_T_max ? _exptl_absorpt_correction_T_min 0.71964 _exptl_absorpt_correction_T_max 1.00000 _diffrn_ambient_temperature 293(2) _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Xcalibur Atlas Gemini ultra' _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.4186 _diffrn_reflns_number 7946 _diffrn_reflns_av_R_equivalents 0.0334 _diffrn_reflns_theta_min 2.775 _diffrn_reflns_theta_max 29.590 _diffrn_reflns_theta_full 25.242 _diffrn_measured_fraction_theta_max 0.876 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _refine_special_details ? _reflns_number_total 2508 _reflns_number_gt 1563 _reflns_threshold_expression 'I > 2\s(I)' _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0890 _refine_ls_R_factor_gt 0.0512 _refine_ls_wR_factor_gt 0.1251 _refine_ls_wR_factor_ref 0.1472 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _refine_ls_number_reflns 2508 _refine_ls_number_parameters 149 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0639P)^2^+0.0580P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _atom_sites_solution_secondary ? _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.208 _refine_diff_density_min -0.5 _refine_ls_extinction_method none _refine_ls_extinction_coef . 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' _computing_data_collection ; CrysAlis PRO (Rigaku OD, 2015) ; _computing_cell_refinement ; CrysAlis PRO (Rigaku OD, 2015) ; _computing_data_reduction ; CrysAlis PRO (Rigaku OD, 2015) ; _computing_structure_solution ; SHELXT (Sheldrick, 2015a) ; _computing_structure_refinement ; SHELXL2014 (Sheldrick, 2015b) ; _computing_molecular_graphics ; OLEX2 (Dolomanov et al., 2009) ; _computing_publication_material ; OLEX2 (Dolomanov et al., 2009) ; 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_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O O3 0.6461(3) 0.33269(14) 0.01419(12) 0.0536(4) Uani d 1 . . H H3 0.796(5) 0.389(3) 0.002(3) 0.104(10) Uiso d 1 . . O O1 0.9195(2) 0.59305(13) 0.12532(12) 0.0518(3) Uani d 1 . . O O2 0.0447(3) 0.36386(14) 0.31887(13) 0.0647(4) Uani d 1 . . C C1 0.7232(3) 0.54469(17) 0.17533(15) 0.0388(4) Uani d 1 . . C C2 0.5615(3) 0.39989(17) 0.11881(15) 0.0403(4) Uani d 1 . . C C3 0.3415(3) 0.33844(17) 0.16560(15) 0.0419(4) Uani d 1 . . C C4 0.2483(3) 0.41556(18) 0.27733(16) 0.0431(4) Uani d 1 . . C C5 0.3230(4) 0.6358(2) 0.44404(17) 0.0511(4) Uani d 1 . . H H5 0.1693 0.5951 0.4767 0.061 Uiso calc 1 . . C C6 0.4664(4) 0.7695(2) 0.50175(19) 0.0586(5) Uani d 1 . . H H6 0.4109 0.8182 0.5740 0.070 Uiso calc 1 . . C C7 0.6917(4) 0.8311(2) 0.4525(2) 0.0642(6) Uani d 1 . . H H7 0.7871 0.9218 0.4915 0.077 Uiso calc 1 . . C C8 0.7782(3) 0.7597(2) 0.34557(18) 0.0530(5) Uani d 1 . . H H8 0.9302 0.8021 0.3123 0.064 Uiso calc 1 . . C C9 0.6345(3) 0.62361(16) 0.28851(15) 0.0389(4) Uani d 1 . . C C10 0.4061(3) 0.56178(17) 0.33796(15) 0.0397(4) Uani d 1 . . C C11 0.1798(4) 0.19019(18) 0.10516(18) 0.0536(5) Uani d 1 . . H H11A 0.0054 0.1811 0.1290 0.064 Uiso calc 1 . . H H11B 0.1751 0.1833 0.0103 0.064 Uiso calc 1 . . C C12 0.2779(4) 0.07067(19) 0.14761(17) 0.0552(5) Uani d 1 . . C C13 0.3566(5) -0.0258(2) 0.1781(2) 0.0829(7) Uani d 1 . . H H13 0.4196 -0.1030 0.2026 0.099 Uiso calc 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 O3 0.0570(8) 0.0492(7) 0.0513(7) 0.0084(6) 0.0167(6) -0.0053(5) O1 0.0456(7) 0.0531(7) 0.0548(7) 0.0048(6) 0.0176(6) 0.0060(5) O2 0.0540(8) 0.0635(9) 0.0699(9) -0.0031(6) 0.0256(7) 0.0043(7) C1 0.0372(9) 0.0400(8) 0.0405(8) 0.0091(7) 0.0057(7) 0.0094(6) C2 0.0433(9) 0.0397(9) 0.0391(9) 0.0119(7) 0.0057(7) 0.0047(6) C3 0.0437(9) 0.0374(8) 0.0430(9) 0.0075(7) 0.0018(7) 0.0040(7) C4 0.0395(9) 0.0443(9) 0.0453(9) 0.0061(7) 0.0073(7) 0.0110(7) C5 0.0499(10) 0.0575(11) 0.0468(10) 0.0140(8) 0.0121(8) 0.0047(8) C6 0.0615(12) 0.0620(12) 0.0503(10) 0.0185(10) 0.0071(9) -0.0096(8) C7 0.0615(13) 0.0533(11) 0.0678(13) 0.0076(10) 0.0001(10) -0.0172(9) C8 0.0441(10) 0.0488(10) 0.0611(11) 0.0041(8) 0.0066(8) -0.0004(8) C9 0.0377(9) 0.0390(8) 0.0402(8) 0.0101(7) 0.0019(7) 0.0046(6) C10 0.0389(9) 0.0430(9) 0.0380(8) 0.0106(7) 0.0049(7) 0.0055(7) C11 0.0497(10) 0.0458(10) 0.0582(11) 0.0004(8) 0.0023(9) 0.0006(8) C12 0.0671(12) 0.0395(10) 0.0515(10) 0.0016(9) 0.0070(9) -0.0039(8) C13 0.113(2) 0.0483(12) 0.0862(16) 0.0257(13) -0.0048(14) 0.0002(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 O3 H3 . 0.88(3) ? O3 C2 . 1.3426(19) ? O1 C1 . 1.2217(18) ? O2 C4 . 1.2189(19) ? C1 C2 . 1.485(2) ? C1 C9 . 1.473(2) ? C2 C3 . 1.340(2) ? C3 C4 . 1.465(2) ? C3 C11 . 1.521(2) ? C4 C10 . 1.499(2) ? C5 H5 . 0.9300 ? C5 C6 . 1.376(3) ? C5 C10 . 1.381(2) ? C6 H6 . 0.9300 ? C6 C7 . 1.375(3) ? C7 H7 . 0.9300 ? C7 C8 . 1.384(3) ? C8 H8 . 0.9300 ? C8 C9 . 1.392(2) ? C9 C10 . 1.390(2) ? C11 H11A . 0.9700 ? C11 H11B . 0.9700 ? C11 C12 . 1.458(3) ? C12 C13 . 1.161(3) ? C13 H13 . 0.9300 ? 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 O3 H3 . . 106.5(17) ? O1 C1 C2 . . 118.90(14) ? O1 C1 C9 . . 123.40(15) ? C9 C1 C2 . . 117.69(14) ? O3 C2 C1 . . 115.90(14) ? C3 C2 O3 . . 120.71(15) ? C3 C2 C1 . . 123.38(14) ? C2 C3 C4 . . 119.88(15) ? C2 C3 C11 . . 122.10(15) ? C4 C3 C11 . . 118.01(15) ? O2 C4 C3 . . 121.03(16) ? O2 C4 C10 . . 120.40(15) ? C3 C4 C10 . . 118.56(14) ? C6 C5 H5 . . 119.8 ? C6 C5 C10 . . 120.37(17) ? C10 C5 H5 . . 119.8 ? C5 C6 H6 . . 120.0 ? C7 C6 C5 . . 119.98(17) ? C7 C6 H6 . . 120.0 ? C6 C7 H7 . . 119.6 ? C6 C7 C8 . . 120.80(18) ? C8 C7 H7 . . 119.6 ? C7 C8 H8 . . 120.5 ? C7 C8 C9 . . 119.08(17) ? C9 C8 H8 . . 120.5 ? C8 C9 C1 . . 120.23(15) ? C10 C9 C1 . . 119.71(14) ? C10 C9 C8 . . 120.07(15) ? C5 C10 C4 . . 119.53(15) ? C5 C10 C9 . . 119.69(15) ? C9 C10 C4 . . 120.78(14) ? C3 C11 H11A . . 109.1 ? C3 C11 H11B . . 109.1 ? H11A C11 H11B . . 107.8 ? C12 C11 C3 . . 112.70(14) ? C12 C11 H11A . . 109.1 ? C12 C11 H11B . . 109.1 ? C13 C12 C11 . . 178.3(2) ? C12 C13 H13 . . 180.0 ? 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 O3 . . . . -0.4(2) no O1 C1 C2 C3 . . . . -179.15(16) no C9 C1 C2 O3 . . . . 178.72(14) no C9 C1 C2 C3 . . . . -0.1(2) no O1 C1 C9 C8 . . . . -1.0(2) no O1 C1 C9 C10 . . . . 178.81(15) no C2 C1 C9 C8 . . . . 179.98(14) no C2 C1 C9 C10 . . . . -0.2(2) no O3 C2 C3 C4 . . . . -178.09(15) no O3 C2 C3 C11 . . . . 1.0(2) no C1 C2 C3 C4 . . . . 0.7(2) no C1 C2 C3 C11 . . . . 179.77(15) no C2 C3 C4 O2 . . . . 177.64(16) no C2 C3 C4 C10 . . . . -0.9(2) no C11 C3 C4 O2 . . . . -1.5(2) no C11 C3 C4 C10 . . . . 179.92(15) no C2 C3 C11 C12 . . . . 79.9(2) no C4 C3 C11 C12 . . . . -100.96(19) no O2 C4 C10 C5 . . . . 2.0(3) no O2 C4 C10 C9 . . . . -177.93(16) no C3 C4 C10 C5 . . . . -179.45(16) no C3 C4 C10 C9 . . . . 0.7(2) no C10 C5 C6 C7 . . . . 1.0(3) no C6 C5 C10 C4 . . . . 179.40(17) no C6 C5 C10 C9 . . . . -0.7(3) no C5 C6 C7 C8 . . . . -0.5(3) no C6 C7 C8 C9 . . . . -0.4(3) no C7 C8 C9 C1 . . . . -179.48(16) no C7 C8 C9 C10 . . . . 0.7(3) no C1 C9 C10 C4 . . . . -0.1(2) no C1 C9 C10 C5 . . . . -180.00(16) no C8 C9 C10 C4 . . . . 179.73(15) no C8 C9 C10 C5 . . . . -0.2(2) no 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 O3 H3 O1 2_765 0.89(3) 2.06(3) 2.8118(19) 142(3) C5 H5 O2 2_566 0.93 2.49 3.231(2) 137 _shelx_res_file ; RGI-1.res created by SHELXL-2014/7 TITL RGI-1_a.res in P-1 REM SHELXT solution in P-1 REM R1 0.175, Rweak 0.009, Alpha 0.061, Orientation as input REM Formula found by SHELXT: C12 O4 Rem AFIX 147 Rem H3 2 0.784969 0.381201 -0.000598 11.00000 -1.50000 Rem AFIX 0 CELL 0.71073 5.369516 9.527838 10.297158 96.8135 93.4318 102.9771 ZERR 2 0.000445 0.000803 0.000878 0.007 0.0068 0.0071 LATT 1 SFAC C H O UNIT 26 16 6 L.S. 20 PLAN 20 BOND $H list 4 fmap 2 acta NOHKL REM REM REM WGHT 0.063900 0.058000 FVAR 6.97051 O3 3 0.646149 0.332693 0.014187 11.00000 0.05701 0.04917 = 0.05128 -0.00530 0.01674 0.00837 H3 2 0.795713 0.388672 0.001649 11.00000 0.10408 O1 3 0.919549 0.593050 0.125323 11.00000 0.04560 0.05314 = 0.05477 0.00597 0.01763 0.00475 O2 3 0.044652 0.363856 0.318871 11.00000 0.05395 0.06348 = 0.06993 0.00432 0.02564 -0.00312 C1 1 0.723155 0.544694 0.175333 11.00000 0.03724 0.04002 = 0.04048 0.00944 0.00571 0.00911 C2 1 0.561531 0.399891 0.118815 11.00000 0.04331 0.03973 = 0.03907 0.00466 0.00572 0.01194 C3 1 0.341543 0.338440 0.165605 11.00000 0.04369 0.03745 = 0.04304 0.00405 0.00185 0.00745 C4 1 0.248335 0.415561 0.277329 11.00000 0.03951 0.04435 = 0.04528 0.01098 0.00729 0.00613 C5 1 0.323001 0.635793 0.444036 11.00000 0.04994 0.05748 = 0.04684 0.00472 0.01211 0.01403 AFIX 43 H5 2 0.169297 0.595064 0.476662 11.00000 -1.20000 AFIX 0 C6 1 0.466371 0.769513 0.501753 11.00000 0.06154 0.06202 = 0.05029 -0.00965 0.00711 0.01854 AFIX 43 H6 2 0.410869 0.818201 0.574047 11.00000 -1.20000 AFIX 0 C7 1 0.691662 0.831092 0.452502 11.00000 0.06153 0.05334 = 0.06780 -0.01725 0.00013 0.00757 AFIX 43 H7 2 0.787086 0.921806 0.491494 11.00000 -1.20000 AFIX 0 C8 1 0.778192 0.759703 0.345572 11.00000 0.04412 0.04882 = 0.06115 -0.00037 0.00657 0.00405 AFIX 43 H8 2 0.930220 0.802087 0.312321 11.00000 -1.20000 AFIX 0 C9 1 0.634512 0.623607 0.288508 11.00000 0.03773 0.03896 = 0.04018 0.00455 0.00191 0.01014 C10 1 0.406098 0.561775 0.337962 11.00000 0.03889 0.04299 = 0.03797 0.00550 0.00494 0.01056 C11 1 0.179817 0.190193 0.105163 11.00000 0.04972 0.04582 = 0.05819 0.00059 0.00225 0.00040 AFIX 23 H11A 2 0.005432 0.181082 0.129043 11.00000 -1.20000 H11B 2 0.175133 0.183317 0.010267 11.00000 -1.20000 AFIX 0 C12 1 0.277914 0.070668 0.147612 11.00000 0.06708 0.03954 = 0.05146 -0.00393 0.00704 0.00158 C13 1 0.356572 -0.025802 0.178140 11.00000 0.11348 0.04834 = 0.08615 0.00016 -0.00483 0.02573 AFIX 163 H13 2 0.419554 -0.103045 0.202584 11.00000 -1.20000 AFIX 0 HKLF 4 REM laus_a.res in P-1 REM R1 = 0.0512 for 1563 Fo > 4sig(Fo) and 0.0890 for all 2508 data REM 149 parameters refined using 0 restraints END WGHT 0.0629 0.0647 REM Highest difference peak 0.208, deepest hole -0.195, 1-sigma level 0.038 Q1 1 0.3484 0.4847 0.3193 11.00000 0.05 0.21 Q2 1 0.2717 0.2583 0.1620 11.00000 0.05 0.17 Q3 1 0.6045 0.4862 0.1276 11.00000 0.05 0.17 Q4 1 0.6774 0.5760 0.2433 11.00000 0.05 0.17 Q5 1 0.7266 0.6646 0.3367 11.00000 0.05 0.15 Q6 1 0.3213 0.3788 0.2133 11.00000 0.05 0.15 Q7 1 0.4932 0.0355 0.1756 11.00000 0.05 0.14 Q8 1 0.4058 0.4079 0.1181 11.00000 0.05 0.14 Q9 1 0.6727 0.7030 0.2824 11.00000 0.05 0.14 Q10 1 0.6462 0.4579 0.1651 11.00000 0.05 0.13 Q11 1 0.4964 0.3441 0.1864 11.00000 0.05 0.12 Q12 1 -0.0213 0.1560 0.2419 11.00000 0.05 0.12 Q13 1 0.4740 0.6243 0.2852 11.00000 0.05 0.11 Q14 1 0.9511 0.5033 0.0639 11.00000 0.05 0.11 Q15 1 0.2858 0.0068 0.2227 11.00000 0.05 0.11 Q16 1 0.7748 0.4565 -0.0954 11.00000 0.05 0.10 Q17 1 0.1123 0.1593 -0.1409 11.00000 0.05 0.10 Q18 1 -0.0061 0.2052 0.0824 11.00000 0.05 0.10 Q19 1 1.0004 0.7537 0.3557 11.00000 0.05 0.10 Q20 1 0.4301 0.6815 0.4787 11.00000 0.05 0.10 ; _shelx_res_checksum 57674