############################################################################## # # # 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_global _audit_creation_method 'form.cif (version 2.0)' _journal_data_validation_number ? _journal_date_recd_electronic 2011-11-19 _journal_date_accepted 2011-11-21 _journal_name_full 'Acta Crystallographica, Section E' _journal_year 2011 _journal_volume 67 _journal_issue 12 _journal_page_first o3437 _journal_page_last o3437 _journal_paper_category QO _journal_coeditor_code FF2044 _publ_contact_author_name 'Dr. Kargar, Hadi' _publ_contact_author_address ; Department of Chemistry, Payame Noor University, PO Box 19395-3697 Tehran, Iran ; _publ_contact_author_email 'hkargar@pnu.ac.ir' _publ_contact_author_fax ? _publ_contact_author_phone ? _publ_section_title ;\ (E)-5-[(3-Ethoxy-2-hydroxybenzylidene)amino]-1,3,4-thiadiazole-\ 2(3H)-thione ; loop_ _publ_author_name _publ_author_address 'Kargar, Hadi' ; Department of Chemistry, Payame Noor University, PO BOX 19395-3697 Tehran, Iran ; 'Kia, Reza' ; X-ray Crystallography Lab. Plasma Physics Research Center, Science and Research Branch, Islamic Azad University, Tehran Iran and Department of Chemistry, Science and Research Branch, Islamic Azad University, Tehran, Iran ; data_I _audit_creation_method SHELXL-97 _chemical_name_systematic ; (E)-5-[(3-Ethoxy-2-hydroxybenzylidene)amino]-1,3,4-thiadiazole- 2(3H)-thione ; _chemical_name_common ; ; _chemical_formula_moiety 'C11 H11 N3 O2 S2' _chemical_formula_sum 'C11 H11 N3 O2 S2' _chemical_formula_iupac 'C11 H11 N3 O2 S2' _chemical_formula_weight 281.35 _chemical_melting_point ? _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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' _cell_length_a 8.9250(10) _cell_length_b 11.3664(14) _cell_length_c 12.8945(16) _cell_angle_alpha 90.00 _cell_angle_beta 99.352(9) _cell_angle_gamma 90.00 _cell_volume 1290.7(3) _cell_formula_units_Z 4 _cell_measurement_reflns_used 8153 _cell_measurement_theta_min 1.79 _cell_measurement_theta_max 29.56 _cell_measurement_temperature 291(2) _exptl_crystal_description 'Block' _exptl_crystal_colour 'yellow' _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.15 _exptl_crystal_density_diffrn 1.448 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.409 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [MULABS (Blessing, 1995) in PLATON (Spek, 2009)] ; _exptl_absorpt_correction_T_min 0.9046 _exptl_absorpt_correction_T_max 0.9411 _exptl_special_details ? _diffrn_ambient_temperature 291(2) _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'graphite' _diffrn_measurement_device_type 'Stoe IPDS 2T Image Plate' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 10227 _diffrn_reflns_av_R_equivalents 0.0361 _diffrn_reflns_av_sigmaI/netI 0.0408 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 29.17 _diffrn_reflns_theta_full 29.17 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 17 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > \s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _reflns_number_total 3461 _reflns_number_gt 2376 _reflns_threshold_expression I>2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0799 _refine_ls_R_factor_gt 0.0460 _refine_ls_wR_factor_gt 0.0928 _refine_ls_wR_factor_ref 0.1027 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _refine_ls_number_reflns 3461 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0529P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.240 _refine_diff_density_min -0.303 _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' 'N' 'N' 0.0061 0.0033 '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' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection 'X-AREA (Stoe & Cie, 2009)' _computing_cell_refinement 'X-AREA (Stoe & Cie, 2009)' _computing_data_reduction 'X-AREA (Stoe & Cie, 2009)' _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement 'SHELXTL (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material ; SHELXTL (Sheldrick, 2008) and PLATON (Spek, 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_refinement_flags _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_disorder_assembly _atom_site_disorder_group S S1 0.87646(6) 0.66233(4) 0.17887(4) 0.04681(15) Uani d . 1 1 . . S S2 0.95905(7) 0.83877(5) 0.35481(6) 0.0674(2) Uani d . 1 1 . . O O1 0.46721(15) 0.31614(11) 0.07089(10) 0.0420(3) Uani d . 1 1 . . H H1 0.5138 0.3743 0.1056 0.063 Uiso d R 1 1 . . O O2 0.37731(16) 0.13586(11) -0.04539(11) 0.0464(3) Uani d . 1 1 . . N N1 0.66203(16) 0.48422(12) 0.12047(11) 0.0343(3) Uani d . 1 1 . . N N2 0.65853(18) 0.59227(13) 0.27073(13) 0.0431(4) Uani d . 1 1 . . N N3 0.73429(19) 0.68024(13) 0.32832(13) 0.0459(4) Uani d . 1 1 . . H H3 0.7041 0.7048 0.3820 0.055 Uiso d R 1 1 . . C C1 0.54149(19) 0.29557(15) -0.01085(12) 0.0324(4) Uani d . 1 1 . . C C2 0.4937(2) 0.19863(15) -0.07513(14) 0.0364(4) Uani d . 1 1 . . C C3 0.5647(3) 0.17501(17) -0.16015(15) 0.0473(5) Uani d . 1 1 . . H H3A 0.5343 0.1104 -0.2026 0.057 Uiso calc R 1 1 . . C C4 0.6810(3) 0.2464(2) -0.18320(17) 0.0564(6) Uani d . 1 1 . . H H4A 0.7274 0.2295 -0.2410 0.068 Uiso calc R 1 1 . . C C5 0.7277(2) 0.34171(19) -0.12110(16) 0.0481(5) Uani d . 1 1 . . H H5A 0.8046 0.3900 -0.1376 0.058 Uiso calc R 1 1 . . C C6 0.6600(2) 0.36673(15) -0.03266(13) 0.0348(4) Uani d . 1 1 . . C C7 0.7168(2) 0.46283(15) 0.03607(14) 0.0355(4) Uani d . 1 1 . . H H7A 0.7943 0.5100 0.0190 0.043 Uiso calc R 1 1 . . C C8 0.72069(18) 0.57225(14) 0.18892(13) 0.0327(4) Uani d . 1 1 . . C C9 0.8533(2) 0.73096(16) 0.29585(15) 0.0410(4) Uani d . 1 1 . . C C10 0.3216(3) 0.03555(18) -0.10841(18) 0.0571(6) Uani d . 1 1 . . H H10A 0.3994 -0.0246 -0.1040 0.069 Uiso calc R 1 1 . . H H10B 0.2931 0.0585 -0.1814 0.069 Uiso calc R 1 1 . . C C11 0.1864(3) -0.0103(2) -0.0663(2) 0.0802(8) Uani d . 1 1 . . H H11A 0.1507 -0.0808 -0.1032 0.120 Uiso calc R 1 1 . . H H11B 0.1073 0.0479 -0.0759 0.120 Uiso calc R 1 1 . . H H11C 0.2143 -0.0273 0.0072 0.120 Uiso calc R 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 S1 0.0386(3) 0.0513(3) 0.0539(3) -0.0096(2) 0.0173(2) -0.0106(2) S2 0.0545(3) 0.0618(4) 0.0836(5) -0.0179(3) 0.0043(3) -0.0267(3) O1 0.0520(8) 0.0428(7) 0.0348(7) -0.0101(6) 0.0177(6) -0.0064(5) O2 0.0550(8) 0.0394(7) 0.0444(8) -0.0097(6) 0.0067(6) -0.0034(6) N1 0.0360(8) 0.0322(7) 0.0349(8) 0.0024(6) 0.0061(6) -0.0007(6) N2 0.0478(9) 0.0386(8) 0.0459(9) -0.0094(7) 0.0163(7) -0.0090(7) N3 0.0511(10) 0.0440(8) 0.0460(9) -0.0089(7) 0.0174(8) -0.0154(7) C1 0.0367(9) 0.0349(8) 0.0261(8) 0.0069(7) 0.0062(7) 0.0013(6) C2 0.0406(9) 0.0347(8) 0.0322(9) 0.0042(7) 0.0011(7) 0.0025(7) C3 0.0592(12) 0.0446(10) 0.0378(10) 0.0063(9) 0.0066(9) -0.0100(8) C4 0.0604(13) 0.0683(14) 0.0451(12) 0.0048(11) 0.0221(10) -0.0173(10) C5 0.0426(10) 0.0616(12) 0.0438(11) -0.0024(9) 0.0182(9) -0.0077(9) C6 0.0349(9) 0.0398(9) 0.0301(8) 0.0054(7) 0.0065(7) -0.0012(7) C7 0.0310(9) 0.0384(9) 0.0372(9) 0.0012(7) 0.0062(7) 0.0019(7) C8 0.0323(8) 0.0297(8) 0.0369(9) 0.0020(7) 0.0077(7) 0.0006(7) C9 0.0359(9) 0.0380(9) 0.0478(11) 0.0030(8) 0.0031(8) -0.0062(8) C10 0.0692(15) 0.0437(11) 0.0527(13) -0.0090(10) -0.0070(11) -0.0053(9) C11 0.0754(18) 0.0700(16) 0.090(2) -0.0320(14) -0.0014(15) -0.0004(14) _geom_special_details ; All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 S1 C9 . 1.7400(19) ? S1 C8 . 1.7483(17) ? S2 C9 . 1.6544(19) ? O1 C1 . 1.354(2) ? O1 H1 . 0.8659 ? O2 C2 . 1.365(2) ? O2 C10 . 1.441(2) ? N1 C7 . 1.287(2) ? N1 C8 . 1.380(2) ? N2 C8 . 1.290(2) ? N2 N3 . 1.358(2) ? N3 C9 . 1.335(2) ? N3 H3 . 0.8311 ? C1 C6 . 1.396(2) ? C1 C2 . 1.403(2) ? C2 C3 . 1.379(3) ? C3 C4 . 1.387(3) ? C3 H3A . 0.9300 ? C4 C5 . 1.371(3) ? C4 H4A . 0.9300 ? C5 C6 . 1.404(3) ? C5 H5A . 0.9300 ? C6 C7 . 1.446(2) ? C7 H7A . 0.9300 ? C10 C11 . 1.495(3) ? C10 H10A . 0.9700 ? C10 H10B . 0.9700 ? C11 H11A . 0.9600 ? C11 H11B . 0.9600 ? C11 H11C . 0.9600 ? 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 C9 S1 C8 . . 89.45(9) ? C1 O1 H1 . . 106.2 ? C2 O2 C10 . . 117.63(16) ? C7 N1 C8 . . 121.41(15) ? C8 N2 N3 . . 109.58(15) ? C9 N3 N2 . . 119.82(15) ? C9 N3 H3 . . 119.9 ? N2 N3 H3 . . 120.2 ? O1 C1 C6 . . 122.67(15) ? O1 C1 C2 . . 117.08(15) ? C6 C1 C2 . . 120.25(16) ? O2 C2 C3 . . 126.19(16) ? O2 C2 C1 . . 114.63(15) ? C3 C2 C1 . . 119.18(17) ? C2 C3 C4 . . 120.87(18) ? C2 C3 H3A . . 119.6 ? C4 C3 H3A . . 119.6 ? C5 C4 C3 . . 120.29(18) ? C5 C4 H4A . . 119.9 ? C3 C4 H4A . . 119.9 ? C4 C5 C6 . . 120.27(19) ? C4 C5 H5A . . 119.9 ? C6 C5 H5A . . 119.9 ? C1 C6 C5 . . 119.12(16) ? C1 C6 C7 . . 121.06(15) ? C5 C6 C7 . . 119.78(17) ? N1 C7 C6 . . 121.18(16) ? N1 C7 H7A . . 119.4 ? C6 C7 H7A . . 119.4 ? N2 C8 N1 . . 118.84(15) ? N2 C8 S1 . . 114.22(13) ? N1 C8 S1 . . 126.94(13) ? N3 C9 S2 . . 126.83(15) ? N3 C9 S1 . . 106.92(13) ? S2 C9 S1 . . 126.25(12) ? O2 C10 C11 . . 107.2(2) ? O2 C10 H10A . . 110.3 ? C11 C10 H10A . . 110.3 ? O2 C10 H10B . . 110.3 ? C11 C10 H10B . . 110.3 ? H10A C10 H10B . . 108.5 ? C10 C11 H11A . . 109.5 ? C10 C11 H11B . . 109.5 ? H11A C11 H11B . . 109.5 ? C10 C11 H11C . . 109.5 ? H11A C11 H11C . . 109.5 ? H11B C11 H11C . . 109.5 ? 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 C8 N2 N3 C9 . . . . 0.1(3) ? C10 O2 C2 C3 . . . . -0.4(3) ? C10 O2 C2 C1 . . . . 179.53(16) ? O1 C1 C2 O2 . . . . -0.7(2) ? C6 C1 C2 O2 . . . . 179.79(15) ? O1 C1 C2 C3 . . . . 179.21(16) ? C6 C1 C2 C3 . . . . -0.3(3) ? O2 C2 C3 C4 . . . . 179.21(19) ? C1 C2 C3 C4 . . . . -0.7(3) ? C2 C3 C4 C5 . . . . 0.3(3) ? C3 C4 C5 C6 . . . . 1.0(3) ? O1 C1 C6 C5 . . . . -177.84(16) ? C2 C1 C6 C5 . . . . 1.6(3) ? O1 C1 C6 C7 . . . . 4.2(3) ? C2 C1 C6 C7 . . . . -176.35(15) ? C4 C5 C6 C1 . . . . -2.0(3) ? C4 C5 C6 C7 . . . . 175.99(19) ? C8 N1 C7 C6 . . . . 176.85(15) ? C1 C6 C7 N1 . . . . 1.4(3) ? C5 C6 C7 N1 . . . . -176.53(17) ? N3 N2 C8 N1 . . . . 178.96(15) ? N3 N2 C8 S1 . . . . -0.3(2) ? C7 N1 C8 N2 . . . . 177.93(17) ? C7 N1 C8 S1 . . . . -2.9(2) ? C9 S1 C8 N2 . . . . 0.27(15) ? C9 S1 C8 N1 . . . . -178.89(16) ? N2 N3 C9 S2 . . . . 179.90(14) ? N2 N3 C9 S1 . . . . 0.1(2) ? C8 S1 C9 N3 . . . . -0.18(14) ? C8 S1 C9 S2 . . . . 179.99(14) ? C2 O2 C10 C11 . . . . -174.57(18) ? 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 O1 H1 N1 . 0.87 1.81 2.5924(19) 150 y N3 H3 O1 2_655 0.83 2.15 2.841(2) 141 y N3 H3 O2 2_655 0.83 2.47 3.160(2) 142 y C3 H3A N2 4_565 0.93 2.60 3.312(3) 133 y _iucr_refine_instructions_details ; TITL a in P2(1)/c CELL 0.71073 8.9250 11.3664 12.8945 90.000 99.352 90.000 ZERR 4.00 0.0010 0.0014 0.0016 0.000 0.009 0.000 LATT 1 SYMM -X, 0.5+Y, 0.5-Z SFAC C H N O S UNIT 44 44 12 8 8 SIZE 0.15 0.22 0.25 L.S. 10 BOND $H FMAP 2 1 60 PLAN 20 CONF ACTA WGHT 0.052900 FVAR 0.84140 S1 5 0.876464 0.662335 0.178866 11.00000 0.03855 0.05126 = 0.05387 -0.01056 0.01728 -0.00965 S2 5 0.959052 0.838773 0.354808 11.00000 0.05447 0.06177 = 0.08364 -0.02670 0.00431 -0.01793 O1 4 0.467215 0.316144 0.070889 11.00000 0.05202 0.04279 = 0.03481 -0.00635 0.01771 -0.01014 AFIX 3 H1 2 0.513810 0.374305 0.105595 11.00000 -1.50000 AFIX 0 O2 4 0.377311 0.135857 -0.045394 11.00000 0.05497 0.03944 = 0.04441 -0.00339 0.00674 -0.00973 N1 3 0.662028 0.484220 0.120470 11.00000 0.03598 0.03216 = 0.03489 -0.00075 0.00614 0.00236 N2 3 0.658527 0.592274 0.270733 11.00000 0.04785 0.03858 = 0.04587 -0.00898 0.01625 -0.00940 N3 3 0.734288 0.680237 0.328325 11.00000 0.05106 0.04399 = 0.04597 -0.01541 0.01744 -0.00889 AFIX 3 H3 2 0.704085 0.704826 0.382017 11.00000 -1.20000 AFIX 0 C1 1 0.541493 0.295565 -0.010849 11.00000 0.03672 0.03488 = 0.02605 0.00125 0.00622 0.00685 C2 1 0.493665 0.198626 -0.075130 11.00000 0.04057 0.03474 = 0.03222 0.00247 0.00110 0.00420 C3 1 0.564707 0.175008 -0.160151 11.00000 0.05919 0.04460 = 0.03780 -0.00996 0.00657 0.00632 AFIX 43 H3A 2 0.534253 0.110363 -0.202590 11.00000 -1.20000 AFIX 0 C4 1 0.680966 0.246387 -0.183201 11.00000 0.06041 0.06834 = 0.04509 -0.01735 0.02209 0.00483 AFIX 43 H4A 2 0.727412 0.229536 -0.241025 11.00000 -1.20000 AFIX 0 C5 1 0.727737 0.341709 -0.121099 11.00000 0.04265 0.06158 = 0.04376 -0.00765 0.01818 -0.00240 AFIX 43 H5A 2 0.804629 0.389968 -0.137640 11.00000 -1.20000 AFIX 0 C6 1 0.660015 0.366729 -0.032662 11.00000 0.03489 0.03978 = 0.03010 -0.00118 0.00646 0.00539 C7 1 0.716813 0.462828 0.036067 11.00000 0.03105 0.03840 = 0.03723 0.00192 0.00621 0.00120 AFIX 43 H7A 2 0.794343 0.510040 0.018975 11.00000 -1.20000 AFIX 0 C8 1 0.720695 0.572245 0.188916 11.00000 0.03229 0.02966 = 0.03694 0.00058 0.00770 0.00196 C9 1 0.853328 0.730957 0.295845 11.00000 0.03591 0.03803 = 0.04776 -0.00619 0.00307 0.00296 C10 1 0.321571 0.035549 -0.108406 11.00000 0.06923 0.04366 = 0.05274 -0.00531 -0.00702 -0.00897 AFIX 23 H10A 2 0.399445 -0.024598 -0.104037 11.00000 -1.20000 H10B 2 0.293131 0.058489 -0.181410 11.00000 -1.20000 AFIX 0 C11 1 0.186351 -0.010269 -0.066332 11.00000 0.07536 0.07001 = 0.09019 -0.00043 -0.00140 -0.03199 AFIX 137 H11A 2 0.150682 -0.080819 -0.103237 11.00000 -1.50000 H11B 2 0.107274 0.047861 -0.075938 11.00000 -1.50000 H11C 2 0.214263 -0.027272 0.007198 11.00000 -1.50000 HKLF 4 END ;