#------------------------------------------------------------------------------ #$Date: 2020-05-19 07:20:20 +0300 (Tue, 19 May 2020) $ #$Revision: 252168 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/05/7240554.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_7240554 loop_ _publ_author_name 'Zeng, Ziyu' 'Qasem, Ashraf M. A.' 'Kociok-K\"ohn, Gabriele' 'Rowan, Michael G.' 'Blagbrough, Ian S.' _publ_section_title ; The 1\a-hydroxy-A-rings of norditerpenoid alkaloids are twisted-boat conformers ; _journal_issue 32 _journal_name_full 'RSC Advances' _journal_page_first 18797 _journal_paper_doi 10.1039/D0RA03811C _journal_volume 10 _journal_year 2020 _chemical_absolute_configuration ad _chemical_formula_moiety 'C25 H39 N O6' _chemical_formula_sum 'C25 H39 N O6' _chemical_formula_weight 449.57 _chemical_name_common condelphine _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2020-03-17 deposited with the CCDC. 2020-05-04 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 93.4553(9) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 8.92530(9) _cell_length_b 13.08371(15) _cell_length_c 9.80866(10) _cell_measurement_reflns_used 15011 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 72.9710 _cell_measurement_theta_min 4.5290 _cell_volume 1143.33(2) _computing_cell_refinement 'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)' _computing_data_collection 'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)' _computing_data_reduction 'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)' _computing_molecular_graphics 'ORTEP3 for Windows - Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565' _computing_publication_material ; 'WinGX publication routines, Farrugia, L. J., J. Appl. Crystallogr., 1999, 32, 837-838 ; _computing_structure_refinement ; SHELXL-2018/3 (Sheldrick, 2018) Sheldrick GM (2008) Acta Crystallogr A64:112--122 and C. B. H\"ubschle, G. M. Sheldrick and B. Dittrich ShelXle: a Qt graphical user interface for SHELXL J. Appl. Cryst., 44, (2011) 1281-1284. ; _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 150.00(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 8.1150 _diffrn_detector_type EosS2 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at home/near, EosS2' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0245 _diffrn_reflns_av_unetI/netI 0.0182 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 18838 _diffrn_reflns_point_group_measured_fraction_full 0.959 _diffrn_reflns_point_group_measured_fraction_max 0.949 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 72.905 _diffrn_reflns_theta_min 4.516 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.747 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.467 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro 1.171.40.43a (Rigaku Oxford Diffraction, 2019) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.306 _exptl_crystal_description tabloid _exptl_crystal_F_000 488 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: EtOAc/DCM' _exptl_crystal_size_max 0.388 _exptl_crystal_size_mid 0.374 _exptl_crystal_size_min 0.094 _refine_diff_density_max 0.184 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.048 _refine_ls_abs_structure_details ; Flack x determined using 1907 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.02(5) _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 301 _refine_ls_number_reflns 4338 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.062 _refine_ls_R_factor_all 0.0301 _refine_ls_R_factor_gt 0.0299 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0486P)^2^+0.1687P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0757 _refine_ls_wR_factor_ref 0.0759 _reflns_Friedel_coverage 0.818 _reflns_Friedel_fraction_full 0.914 _reflns_Friedel_fraction_max 0.895 _reflns_number_gt 4299 _reflns_number_total 4338 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ra03811c2.cif _cod_data_source_block condelphine _cod_original_sg_symbol_H-M 'P 21' _cod_database_code 7240554 _shelx_shelxl_version_number 2018/3 _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. ; _shelx_estimated_absorpt_t_min 0.760 _shelx_estimated_absorpt_t_max 0.933 _oxdiff_exptl_absorpt_empirical_full_min 0.696 _oxdiff_exptl_absorpt_empirical_full_max 1.187 _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _shelx_res_file ; TITL shelxt_a.res in P2(1) s20phar1.res created by SHELXL-2018/3 at 14:59:11 on 25-Feb-2020 CELL 1.54184 8.92530 13.08371 9.80866 90.000 93.4553 90.000 ZERR 2.00 0.00009 0.00015 0.00010 0.000 0.0009 0.000 LATT -1 SYMM - X, 1/2 + Y, - Z SFAC C H N O UNIT 50 78 2 12 ACTA FMAP 2 PLAN 10 BOND $H CONF TEMP -123 EQIV $1 x-1, y, z HTAB O4 O2 HTAB O4 O6_$1 HTAB O6 N SIZE 0.094 0.374 0.388 LIST 4 L.S. 10 WGHT 0.048600 0.168700 FVAR 10.07065 C1 1 0.161723 0.429727 0.768280 11.00000 0.02302 0.03982 = 0.03248 0.01171 0.00694 0.00151 AFIX 137 H1A 2 0.110321 0.432631 0.677214 11.00000 -1.50000 H1B 2 0.097449 0.459935 0.835116 11.00000 -1.50000 H1C 2 0.183026 0.358347 0.792738 11.00000 -1.50000 AFIX 0 C2 1 0.306004 0.488233 0.767933 11.00000 0.02032 0.03103 = 0.02235 0.00251 0.00484 0.00536 C3 1 0.503701 0.534101 0.629001 11.00000 0.01676 0.01876 = 0.01733 -0.00274 0.00175 -0.00099 AFIX 13 H3 2 0.514675 0.602330 0.674456 11.00000 -1.20000 AFIX 0 C4 1 0.626928 0.461845 0.684062 11.00000 0.01634 0.01717 = 0.01421 -0.00073 -0.00089 -0.00155 AFIX 13 H4 2 0.636184 0.463741 0.786142 11.00000 -1.20000 AFIX 0 C5 1 0.597668 0.352337 0.632710 11.00000 0.01707 0.01782 = 0.01915 0.00051 -0.00009 -0.00214 AFIX 13 H5 2 0.696214 0.316680 0.627151 11.00000 -1.20000 AFIX 0 C6 1 0.579093 0.275846 0.853289 11.00000 0.05302 0.03321 = 0.02267 0.00913 -0.01107 -0.01528 AFIX 137 H6A 2 0.679720 0.248284 0.842162 11.00000 -1.50000 H6B 2 0.520007 0.226064 0.901940 11.00000 -1.50000 H6C 2 0.587077 0.339533 0.905813 11.00000 -1.50000 AFIX 0 C7 1 0.510910 0.345631 0.492082 11.00000 0.01746 0.01887 = 0.01750 -0.00321 0.00018 -0.00524 AFIX 23 H7A 2 0.407508 0.322978 0.507705 11.00000 -1.20000 H7B 2 0.557911 0.290918 0.439539 11.00000 -1.20000 AFIX 0 C8 1 0.498813 0.442263 0.399640 11.00000 0.01081 0.01945 = 0.01620 -0.00231 -0.00235 -0.00138 C9 1 0.537133 0.542570 0.478521 11.00000 0.01406 0.01704 = 0.01527 -0.00101 0.00115 0.00131 AFIX 13 H9 2 0.480882 0.601315 0.434898 11.00000 -1.20000 AFIX 0 C10 1 0.707937 0.565725 0.490102 11.00000 0.01518 0.01493 = 0.01469 -0.00211 -0.00071 -0.00163 AFIX 13 H10 2 0.720168 0.640828 0.506088 11.00000 -1.20000 AFIX 0 C11 1 0.765869 0.509785 0.623966 11.00000 0.01655 0.02084 = 0.01396 -0.00100 -0.00185 -0.00427 AFIX 23 H11A 2 0.839521 0.456220 0.603372 11.00000 -1.20000 H11B 2 0.814673 0.558916 0.689311 11.00000 -1.20000 AFIX 0 C12 1 0.800076 0.537276 0.367153 11.00000 0.01206 0.01564 = 0.01345 -0.00034 -0.00049 -0.00067 C13 1 0.764337 0.426500 0.325503 11.00000 0.01177 0.01500 = 0.01218 -0.00164 -0.00033 -0.00064 AFIX 13 H13 2 0.775626 0.380561 0.406954 11.00000 -1.20000 AFIX 0 C14 1 0.852372 0.284391 0.185663 11.00000 0.02310 0.01885 = 0.02025 -0.00331 0.00051 0.00287 AFIX 23 H14A 2 0.915177 0.268951 0.108430 11.00000 -1.20000 H14B 2 0.746710 0.269618 0.155613 11.00000 -1.20000 AFIX 0 C15 1 0.899231 0.214996 0.305120 11.00000 0.03689 0.01939 = 0.02757 0.00211 0.00131 0.00682 AFIX 137 H15A 2 0.910777 0.144915 0.272083 11.00000 -1.50000 H15B 2 0.822200 0.216546 0.372189 11.00000 -1.50000 H15C 2 0.994911 0.238812 0.348060 11.00000 -1.50000 AFIX 0 C16 1 0.851401 0.454620 0.093591 11.00000 0.02100 0.02070 = 0.01406 -0.00030 0.00229 0.00083 AFIX 23 H16A 2 0.755306 0.437243 0.043247 11.00000 -1.20000 H16B 2 0.933776 0.436841 0.034653 11.00000 -1.20000 AFIX 0 C17 1 0.855495 0.570017 0.122120 11.00000 0.01886 0.01866 = 0.01445 0.00118 0.00046 -0.00082 C18 1 0.806102 0.624543 -0.010908 11.00000 0.02619 0.02038 = 0.01523 0.00100 -0.00067 -0.00072 AFIX 23 H18A 2 0.876702 0.608387 -0.081941 11.00000 -1.20000 H18B 2 0.704934 0.600642 -0.043419 11.00000 -1.20000 AFIX 0 C19 1 0.741234 0.785821 -0.104001 11.00000 0.03735 0.03135 = 0.02730 0.01158 -0.00203 0.00726 AFIX 137 H19A 2 0.802486 0.773875 -0.182086 11.00000 -1.50000 H19B 2 0.739909 0.859057 -0.083154 11.00000 -1.50000 H19C 2 0.638524 0.762102 -0.126315 11.00000 -1.50000 AFIX 0 C20 1 1.017909 0.604750 0.167661 11.00000 0.01978 0.02653 = 0.01893 0.00437 0.00163 -0.00426 AFIX 23 H20A 2 1.088036 0.547704 0.153072 11.00000 -1.20000 H20B 2 1.046445 0.662463 0.109318 11.00000 -1.20000 AFIX 0 C21 1 1.035223 0.637755 0.316782 11.00000 0.02018 0.02435 = 0.02203 0.00071 -0.00035 -0.00892 AFIX 23 H21A 2 1.143023 0.647297 0.343622 11.00000 -1.20000 H21B 2 0.983934 0.704083 0.327727 11.00000 -1.20000 AFIX 0 C22 1 0.969078 0.558707 0.410007 11.00000 0.01433 0.01999 = 0.01527 -0.00037 -0.00188 -0.00351 AFIX 13 H22 2 0.972020 0.589297 0.503559 11.00000 -1.20000 AFIX 0 C23 1 0.742742 0.591785 0.233298 11.00000 0.01530 0.01480 = 0.01436 0.00066 -0.00117 0.00003 AFIX 13 H23 2 0.729638 0.666831 0.247798 11.00000 -1.20000 AFIX 0 C24 1 0.590092 0.538346 0.197137 11.00000 0.01512 0.02010 = 0.01456 -0.00009 -0.00178 0.00138 AFIX 23 H24A 2 0.505777 0.580891 0.225706 11.00000 -1.20000 H24B 2 0.576500 0.525786 0.097630 11.00000 -1.20000 AFIX 0 C25 1 0.597685 0.436138 0.276854 11.00000 0.01314 0.01650 = 0.01456 -0.00226 -0.00192 -0.00009 AFIX 13 H25 2 0.566163 0.377794 0.215816 11.00000 -1.20000 AFIX 0 N 3 0.866717 0.393288 0.219496 11.00000 0.01616 0.01669 = 0.01476 -0.00103 0.00188 0.00324 O1 4 0.373416 0.523625 0.866610 11.00000 0.03313 0.06432 = 0.02099 -0.00761 0.00586 -0.00501 O2 4 0.353504 0.495206 0.640368 11.00000 0.01465 0.02749 = 0.01855 -0.00065 0.00298 0.00084 O3 4 0.507347 0.295632 0.722836 11.00000 0.03034 0.02526 = 0.01820 0.00361 -0.00273 -0.01077 O4 4 0.349768 0.447563 0.337011 11.00000 0.01028 0.03507 = 0.01939 -0.00417 -0.00186 0.00067 H4A 2 0.285909 0.457115 0.392296 11.00000 0.03337 O5 4 0.803364 0.731260 0.011524 11.00000 0.03952 0.02105 = 0.02111 0.00541 -0.00522 0.00090 O6 4 1.057777 0.467793 0.419523 11.00000 0.01381 0.02693 = 0.02106 0.00128 -0.00324 0.00019 H6 2 1.024982 0.430200 0.351008 11.00000 0.04900 HKLF 4 REM shelxt_a.res in P2(1) REM wR2 = 0.0759, GooF = S = 1.062, Restrained GooF = 1.062 for all data REM R1 = 0.0299 for 4299 Fo > 4sig(Fo) and 0.0301 for all 4338 data REM 301 parameters refined using 1 restraints END WGHT 0.0486 0.1687 REM Highest difference peak 0.184, deepest hole -0.220, 1-sigma level 0.048 Q1 1 0.5536 0.4413 0.3374 11.00000 0.05 0.18 Q2 1 0.8015 0.5829 0.1752 11.00000 0.05 0.17 Q3 1 0.7514 0.5532 0.4257 11.00000 0.05 0.15 Q4 1 0.8835 0.5491 0.3823 11.00000 0.05 0.14 Q5 1 0.6766 0.4231 0.3000 11.00000 0.05 0.13 Q6 1 0.9982 0.2972 -0.0414 11.00000 0.05 0.13 Q7 1 0.8236 0.5976 0.0533 11.00000 0.05 0.13 Q8 1 0.4944 0.7215 -0.1811 11.00000 0.05 0.13 Q9 1 0.6648 0.5668 0.2118 11.00000 0.05 0.13 Q10 1 0.9361 0.5818 0.1390 11.00000 0.05 0.13 ; _shelx_res_checksum 81821 loop_ _space_group_symop_operation_xyz 'x, y, z' '-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_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.1617(2) 0.4297(2) 0.7683(2) 0.0316(5) Uani 1 1 d . . . . . H1A H 0.110321 0.432631 0.677214 0.047 Uiso 1 1 calc R U . . . H1B H 0.097449 0.459935 0.835116 0.047 Uiso 1 1 calc R U . . . H1C H 0.183026 0.358347 0.792738 0.047 Uiso 1 1 calc R U . . . C2 C 0.3060(2) 0.48823(17) 0.76793(19) 0.0244(4) Uani 1 1 d . . . . . C3 C 0.50370(19) 0.53410(14) 0.62900(17) 0.0176(3) Uani 1 1 d . . . . . H3 H 0.514675 0.602330 0.674456 0.021 Uiso 1 1 calc R U . . . C4 C 0.62693(18) 0.46184(14) 0.68406(17) 0.0160(3) Uani 1 1 d . . . . . H4 H 0.636184 0.463741 0.786142 0.019 Uiso 1 1 calc R U . . . C5 C 0.59767(19) 0.35234(14) 0.63271(18) 0.0181(4) Uani 1 1 d . . . . . H5 H 0.696214 0.316680 0.627151 0.022 Uiso 1 1 calc R U . . . C6 C 0.5791(3) 0.27585(19) 0.8533(2) 0.0368(5) Uani 1 1 d . . . . . H6A H 0.679720 0.248284 0.842162 0.055 Uiso 1 1 calc R U . . . H6B H 0.520007 0.226064 0.901940 0.055 Uiso 1 1 calc R U . . . H6C H 0.587077 0.339533 0.905813 0.055 Uiso 1 1 calc R U . . . C7 C 0.51091(19) 0.34563(15) 0.49208(18) 0.0180(3) Uani 1 1 d . . . . . H7A H 0.407508 0.322978 0.507705 0.022 Uiso 1 1 calc R U . . . H7B H 0.557911 0.290918 0.439539 0.022 Uiso 1 1 calc R U . . . C8 C 0.49881(18) 0.44226(14) 0.39964(17) 0.0156(3) Uani 1 1 d . . . . . C9 C 0.53713(18) 0.54257(14) 0.47852(17) 0.0154(3) Uani 1 1 d . . . . . H9 H 0.480882 0.601315 0.434898 0.019 Uiso 1 1 calc R U . . . C10 C 0.70794(18) 0.56573(14) 0.49010(17) 0.0150(3) Uani 1 1 d . . . . . H10 H 0.720168 0.640828 0.506088 0.018 Uiso 1 1 calc R U . . . C11 C 0.76587(18) 0.50979(14) 0.62397(16) 0.0172(4) Uani 1 1 d . . . . . H11A H 0.839521 0.456220 0.603372 0.021 Uiso 1 1 calc R U . . . H11B H 0.814673 0.558916 0.689311 0.021 Uiso 1 1 calc R U . . . C12 C 0.80008(17) 0.53728(13) 0.36715(16) 0.0138(3) Uani 1 1 d . . . . . C13 C 0.76434(17) 0.42650(13) 0.32550(16) 0.0130(3) Uani 1 1 d . . . . . H13 H 0.775626 0.380561 0.406954 0.016 Uiso 1 1 calc R U . . . C14 C 0.8524(2) 0.28439(15) 0.18566(19) 0.0208(4) Uani 1 1 d . . . . . H14A H 0.915177 0.268951 0.108430 0.025 Uiso 1 1 calc R U . . . H14B H 0.746710 0.269618 0.155613 0.025 Uiso 1 1 calc R U . . . C15 C 0.8992(2) 0.21500(16) 0.3051(2) 0.0280(4) Uani 1 1 d . . . . . H15A H 0.910777 0.144915 0.272083 0.042 Uiso 1 1 calc R U . . . H15B H 0.822200 0.216546 0.372189 0.042 Uiso 1 1 calc R U . . . H15C H 0.994911 0.238812 0.348060 0.042 Uiso 1 1 calc R U . . . C16 C 0.85140(19) 0.45462(15) 0.09359(17) 0.0185(4) Uani 1 1 d . . . . . H16A H 0.755306 0.437243 0.043247 0.022 Uiso 1 1 calc R U . . . H16B H 0.933776 0.436841 0.034653 0.022 Uiso 1 1 calc R U . . . C17 C 0.85549(19) 0.57002(14) 0.12212(18) 0.0173(4) Uani 1 1 d . . . . . C18 C 0.8061(2) 0.62454(15) -0.01091(18) 0.0207(4) Uani 1 1 d . . . . . H18A H 0.876702 0.608387 -0.081941 0.025 Uiso 1 1 calc R U . . . H18B H 0.704934 0.600642 -0.043419 0.025 Uiso 1 1 calc R U . . . C19 C 0.7412(3) 0.78582(18) -0.1040(2) 0.0322(5) Uani 1 1 d . . . . . H19A H 0.802486 0.773875 -0.182086 0.048 Uiso 1 1 calc R U . . . H19B H 0.739909 0.859057 -0.083154 0.048 Uiso 1 1 calc R U . . . H19C H 0.638524 0.762102 -0.126315 0.048 Uiso 1 1 calc R U . . . C20 C 1.0179(2) 0.60475(16) 0.16766(19) 0.0217(4) Uani 1 1 d . . . . . H20A H 1.088036 0.547704 0.153072 0.026 Uiso 1 1 calc R U . . . H20B H 1.046445 0.662463 0.109318 0.026 Uiso 1 1 calc R U . . . C21 C 1.0352(2) 0.63775(16) 0.31678(19) 0.0223(4) Uani 1 1 d . . . . . H21A H 1.143023 0.647297 0.343622 0.027 Uiso 1 1 calc R U . . . H21B H 0.983934 0.704083 0.327727 0.027 Uiso 1 1 calc R U . . . C22 C 0.96908(18) 0.55871(14) 0.41001(17) 0.0166(3) Uani 1 1 d . . . . . H22 H 0.972020 0.589297 0.503559 0.020 Uiso 1 1 calc R U . . . C23 C 0.74274(18) 0.59178(14) 0.23330(17) 0.0149(3) Uani 1 1 d . . . . . H23 H 0.729638 0.666831 0.247798 0.018 Uiso 1 1 calc R U . . . C24 C 0.59009(18) 0.53835(14) 0.19714(16) 0.0167(3) Uani 1 1 d . . . . . H24A H 0.505777 0.580891 0.225706 0.020 Uiso 1 1 calc R U . . . H24B H 0.576500 0.525786 0.097630 0.020 Uiso 1 1 calc R U . . . C25 C 0.59768(18) 0.43614(14) 0.27685(16) 0.0148(3) Uani 1 1 d . . . . . H25 H 0.566163 0.377794 0.215816 0.018 Uiso 1 1 calc R U . . . N N 0.86672(16) 0.39329(12) 0.21950(15) 0.0158(3) Uani 1 1 d . . . . . O1 O 0.37342(18) 0.52363(16) 0.86661(15) 0.0393(4) Uani 1 1 d . . . . . O2 O 0.35350(13) 0.49521(10) 0.64037(12) 0.0202(3) Uani 1 1 d . . . . . O3 O 0.50735(16) 0.29563(11) 0.72284(13) 0.0248(3) Uani 1 1 d . . . . . O4 O 0.34977(13) 0.44756(12) 0.33701(13) 0.0217(3) Uani 1 1 d . . . . . H4A H 0.286(3) 0.457(2) 0.392(3) 0.033(7) Uiso 1 1 d . . . . . O5 O 0.80336(17) 0.73126(11) 0.01152(14) 0.0275(3) Uani 1 1 d . . . . . O6 O 1.05778(13) 0.46779(11) 0.41952(13) 0.0208(3) Uani 1 1 d . . . . . H6 H 1.025(4) 0.430(3) 0.351(3) 0.049(9) Uiso 1 1 d . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0230(9) 0.0398(13) 0.0325(10) 0.0117(10) 0.0069(8) 0.0015(8) C2 0.0203(9) 0.0310(11) 0.0224(9) 0.0025(8) 0.0048(7) 0.0054(8) C3 0.0168(8) 0.0188(9) 0.0173(8) -0.0027(7) 0.0018(6) -0.0010(7) C4 0.0163(7) 0.0172(9) 0.0142(7) -0.0007(6) -0.0009(6) -0.0015(6) C5 0.0171(7) 0.0178(9) 0.0192(8) 0.0005(7) -0.0001(6) -0.0021(6) C6 0.0530(14) 0.0332(13) 0.0227(10) 0.0091(9) -0.0111(9) -0.0153(10) C7 0.0175(8) 0.0189(9) 0.0175(8) -0.0032(7) 0.0002(6) -0.0052(7) C8 0.0108(7) 0.0194(9) 0.0162(7) -0.0023(7) -0.0023(6) -0.0014(6) C9 0.0141(8) 0.0170(9) 0.0153(8) -0.0010(6) 0.0012(6) 0.0013(6) C10 0.0152(8) 0.0149(8) 0.0147(7) -0.0021(6) -0.0007(6) -0.0016(6) C11 0.0166(8) 0.0208(9) 0.0140(7) -0.0010(7) -0.0019(6) -0.0043(7) C12 0.0121(7) 0.0156(8) 0.0134(7) -0.0003(6) -0.0005(6) -0.0007(6) C13 0.0118(7) 0.0150(8) 0.0122(7) -0.0016(6) -0.0003(6) -0.0006(6) C14 0.0231(8) 0.0189(10) 0.0203(8) -0.0033(7) 0.0005(7) 0.0029(7) C15 0.0369(11) 0.0194(10) 0.0276(10) 0.0021(8) 0.0013(8) 0.0068(8) C16 0.0210(8) 0.0207(10) 0.0141(7) -0.0003(7) 0.0023(6) 0.0008(7) C17 0.0189(8) 0.0187(9) 0.0144(7) 0.0012(7) 0.0005(6) -0.0008(7) C18 0.0262(9) 0.0204(10) 0.0152(8) 0.0010(7) -0.0007(7) -0.0007(7) C19 0.0374(11) 0.0314(12) 0.0273(10) 0.0116(9) -0.0020(8) 0.0073(9) C20 0.0198(8) 0.0265(10) 0.0189(8) 0.0044(7) 0.0016(6) -0.0043(7) C21 0.0202(8) 0.0244(10) 0.0220(9) 0.0007(8) -0.0004(7) -0.0089(7) C22 0.0143(8) 0.0200(9) 0.0153(7) -0.0004(7) -0.0019(6) -0.0035(6) C23 0.0153(8) 0.0148(8) 0.0144(7) 0.0007(6) -0.0012(6) 0.0000(6) C24 0.0151(7) 0.0201(9) 0.0146(7) -0.0001(7) -0.0018(6) 0.0014(7) C25 0.0131(7) 0.0165(8) 0.0146(7) -0.0023(7) -0.0019(6) -0.0001(6) N 0.0162(7) 0.0167(7) 0.0148(7) -0.0010(6) 0.0019(5) 0.0032(5) O1 0.0331(8) 0.0643(12) 0.0210(7) -0.0076(7) 0.0059(6) -0.0050(8) O2 0.0147(6) 0.0275(7) 0.0185(6) -0.0007(5) 0.0030(5) 0.0008(5) O3 0.0303(7) 0.0253(7) 0.0182(6) 0.0036(5) -0.0027(5) -0.0108(5) O4 0.0103(5) 0.0351(8) 0.0194(6) -0.0042(6) -0.0019(5) 0.0007(5) O5 0.0395(8) 0.0211(8) 0.0211(6) 0.0054(6) -0.0052(5) 0.0009(6) O6 0.0138(5) 0.0269(8) 0.0211(6) 0.0013(5) -0.0032(5) 0.0002(5) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 -8 0 0.1935 -6 0 0 0.2038 -1 8 0 0.1626 0 0 6 0.0618 0 0 -6 0.0318 4 -5 0 0.2416 6 1 0 0.1681 4 6 0 0.2152 2 0 6 0.1133 -1 -7 4 0.1726 -2 0 -6 0.1029 -3 -7 0 0.2342 3 8 0 0.2032 -2 0 6 0.0997 -1 4 6 0.1106 0 -6 -5 0.1318 -1 -3 -6 0.0754 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O1 C2 O2 123.47(18) . . ? O1 C2 C1 125.73(18) . . ? O2 C2 C1 110.80(17) . . ? O2 C3 C4 114.04(15) . . ? O2 C3 C9 109.66(13) . . ? C4 C3 C9 102.04(13) . . ? O2 C3 H3 110.3 . . ? C4 C3 H3 110.3 . . ? C9 C3 H3 110.3 . . ? C3 C4 C5 110.95(14) . . ? C3 C4 C11 101.09(14) . . ? C5 C4 C11 112.32(14) . . ? C3 C4 H4 110.7 . . ? C5 C4 H4 110.7 . . ? C11 C4 H4 110.7 . . ? O3 C5 C4 111.73(14) . . ? O3 C5 C7 104.51(14) . . ? C4 C5 C7 114.36(15) . . ? O3 C5 H5 108.7 . . ? C4 C5 H5 108.7 . . ? C7 C5 H5 108.7 . . ? O3 C6 H6A 109.5 . . ? O3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? O3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C5 C7 C8 119.22(15) . . ? C5 C7 H7A 107.5 . . ? C8 C7 H7A 107.5 . . ? C5 C7 H7B 107.5 . . ? C8 C7 H7B 107.5 . . ? H7A C7 H7B 107.0 . . ? O4 C8 C25 103.21(12) . . ? O4 C8 C9 110.12(14) . . ? C25 C8 C9 108.37(13) . . ? O4 C8 C7 108.61(14) . . ? C25 C8 C7 113.03(14) . . ? C9 C8 C7 113.04(14) . . ? C3 C9 C8 111.75(14) . . ? C3 C9 C10 101.05(13) . . ? C8 C9 C10 112.82(13) . . ? C3 C9 H9 110.3 . . ? C8 C9 H9 110.3 . . ? C10 C9 H9 110.3 . . ? C12 C10 C9 117.55(13) . . ? C12 C10 C11 112.20(14) . . ? C9 C10 C11 104.11(13) . . ? C12 C10 H10 107.5 . . ? C9 C10 H10 107.5 . . ? C11 C10 H10 107.5 . . ? C4 C11 C10 106.21(13) . . ? C4 C11 H11A 110.5 . . ? C10 C11 H11A 110.5 . . ? C4 C11 H11B 110.5 . . ? C10 C11 H11B 110.5 . . ? H11A C11 H11B 108.7 . . ? C13 C12 C10 108.87(13) . . ? C13 C12 C23 98.98(12) . . ? C10 C12 C23 112.66(14) . . ? C13 C12 C22 114.96(14) . . ? C10 C12 C22 107.25(13) . . ? C23 C12 C22 114.04(13) . . ? N C13 C12 109.57(13) . . ? N C13 C25 115.42(13) . . ? C12 C13 C25 100.76(13) . . ? N C13 H13 110.2 . . ? C12 C13 H13 110.2 . . ? C25 C13 H13 110.2 . . ? N C14 C15 112.92(15) . . ? N C14 H14A 109.0 . . ? C15 C14 H14A 109.0 . . ? N C14 H14B 109.0 . . ? C15 C14 H14B 109.0 . . ? H14A C14 H14B 107.8 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N C16 C17 112.52(14) . . ? N C16 H16A 109.1 . . ? C17 C16 H16A 109.1 . . ? N C16 H16B 109.1 . . ? C17 C16 H16B 109.1 . . ? H16A C16 H16B 107.8 . . ? C18 C17 C16 107.51(14) . . ? C18 C17 C23 110.35(14) . . ? C16 C17 C23 107.38(14) . . ? C18 C17 C20 108.90(14) . . ? C16 C17 C20 110.51(15) . . ? C23 C17 C20 112.08(14) . . ? O5 C18 C17 109.56(14) . . ? O5 C18 H18A 109.8 . . ? C17 C18 H18A 109.8 . . ? O5 C18 H18B 109.8 . . ? C17 C18 H18B 109.8 . . ? H18A C18 H18B 108.2 . . ? O5 C19 H19A 109.5 . . ? O5 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? O5 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C21 C20 C17 113.36(15) . . ? C21 C20 H20A 108.9 . . ? C17 C20 H20A 108.9 . . ? C21 C20 H20B 108.9 . . ? C17 C20 H20B 108.9 . . ? H20A C20 H20B 107.7 . . ? C22 C21 C20 111.30(16) . . ? C22 C21 H21A 109.4 . . ? C20 C21 H21A 109.4 . . ? C22 C21 H21B 109.4 . . ? C20 C21 H21B 109.4 . . ? H21A C21 H21B 108.0 . . ? O6 C22 C21 111.79(14) . . ? O6 C22 C12 112.91(14) . . ? C21 C22 C12 111.24(14) . . ? O6 C22 H22 106.8 . . ? C21 C22 H22 106.8 . . ? C12 C22 H22 106.8 . . ? C24 C23 C12 103.07(14) . . ? C24 C23 C17 110.70(13) . . ? C12 C23 C17 108.34(13) . . ? C24 C23 H23 111.5 . . ? C12 C23 H23 111.5 . . ? C17 C23 H23 111.5 . . ? C25 C24 C23 105.21(13) . . ? C25 C24 H24A 110.7 . . ? C23 C24 H24A 110.7 . . ? C25 C24 H24B 110.7 . . ? C23 C24 H24B 110.7 . . ? H24A C24 H24B 108.8 . . ? C8 C25 C13 110.54(13) . . ? C8 C25 C24 109.93(14) . . ? C13 C25 C24 103.84(13) . . ? C8 C25 H25 110.8 . . ? C13 C25 H25 110.8 . . ? C24 C25 H25 110.8 . . ? C14 N C16 109.71(14) . . ? C14 N C13 113.10(14) . . ? C16 N C13 113.37(13) . . ? C2 O2 C3 116.15(14) . . ? C6 O3 C5 114.14(15) . . ? C8 O4 H4A 112.9(18) . . ? C18 O5 C19 112.40(16) . . ? C22 O6 H6 105(2) . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.498(3) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 O1 1.201(3) . ? C2 O2 1.348(2) . ? C3 O2 1.444(2) . ? C3 C4 1.524(2) . ? C3 C9 1.527(2) . ? C3 H3 1.0000 . ? C4 C5 1.536(3) . ? C4 C11 1.538(2) . ? C4 H4 1.0000 . ? C5 O3 1.438(2) . ? C5 C7 1.543(2) . ? C5 H5 1.0000 . ? C6 O3 1.420(2) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C8 1.556(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 O4 1.4329(19) . ? C8 C25 1.537(2) . ? C8 C9 1.551(2) . ? C9 C10 1.552(2) . ? C9 H9 1.0000 . ? C10 C12 1.546(2) . ? C10 C11 1.564(2) . ? C10 H10 1.0000 . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.534(2) . ? C12 C23 1.553(2) . ? C12 C22 1.567(2) . ? C13 N 1.490(2) . ? C13 C25 1.540(2) . ? C13 H13 1.0000 . ? C14 N 1.467(2) . ? C14 C15 1.521(3) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 N 1.472(2) . ? C16 C17 1.536(3) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.529(2) . ? C17 C23 1.554(2) . ? C17 C20 1.559(2) . ? C18 O5 1.414(2) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 O5 1.423(2) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 C21 1.524(3) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C22 1.523(3) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 O6 1.429(2) . ? C22 H22 1.0000 . ? C23 C24 1.553(2) . ? C23 H23 1.0000 . ? C24 C25 1.549(3) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 H25 1.0000 . ? O4 H4A 0.82(3) . ? O6 H6 0.87(3) . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag O4 H4A O2 0.82(3) 2.52(3) 3.0383(18) 122(2) . yes O4 H4A O6 0.82(3) 2.07(3) 2.7877(17) 145(2) 1_455 yes O6 H6 N 0.87(3) 1.92(3) 2.703(2) 150(3) . yes 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 C3 C4 C5 46.30(18) . . . . ? C9 C3 C4 C5 -71.85(16) . . . . ? O2 C3 C4 C11 165.61(13) . . . . ? C9 C3 C4 C11 47.46(15) . . . . ? C3 C4 C5 O3 -89.09(17) . . . . ? C11 C4 C5 O3 158.59(14) . . . . ? C3 C4 C5 C7 29.37(19) . . . . ? C11 C4 C5 C7 -82.96(18) . . . . ? O3 C5 C7 C8 138.57(15) . . . . ? C4 C5 C7 C8 16.1(2) . . . . ? C5 C7 C8 O4 -139.35(15) . . . . ? C5 C7 C8 C25 106.74(18) . . . . ? C5 C7 C8 C9 -16.8(2) . . . . ? O2 C3 C9 C8 -50.02(18) . . . . ? C4 C3 C9 C8 71.21(16) . . . . ? O2 C3 C9 C10 -170.24(14) . . . . ? C4 C3 C9 C10 -49.02(16) . . . . ? O4 C8 C9 C3 93.94(16) . . . . ? C25 C8 C9 C3 -153.84(13) . . . . ? C7 C8 C9 C3 -27.74(19) . . . . ? O4 C8 C9 C10 -152.99(14) . . . . ? C25 C8 C9 C10 -40.78(18) . . . . ? C7 C8 C9 C10 85.32(17) . . . . ? C3 C9 C10 C12 155.53(15) . . . . ? C8 C9 C10 C12 36.1(2) . . . . ? C3 C9 C10 C11 30.74(17) . . . . ? C8 C9 C10 C11 -88.72(16) . . . . ? C3 C4 C11 C10 -27.41(16) . . . . ? C5 C4 C11 C10 90.91(16) . . . . ? C12 C10 C11 C4 -130.25(15) . . . . ? C9 C10 C11 C4 -2.10(17) . . . . ? C9 C10 C12 C13 -49.84(19) . . . . ? C11 C10 C12 C13 70.82(16) . . . . ? C9 C10 C12 C23 58.9(2) . . . . ? C11 C10 C12 C23 179.56(14) . . . . ? C9 C10 C12 C22 -174.80(14) . . . . ? C11 C10 C12 C22 -54.15(18) . . . . ? C10 C12 C13 N -172.56(13) . . . . ? C23 C12 C13 N 69.65(15) . . . . ? C22 C12 C13 N -52.25(17) . . . . ? C10 C12 C13 C25 65.34(15) . . . . ? C23 C12 C13 C25 -52.44(14) . . . . ? C22 C12 C13 C25 -174.34(13) . . . . ? N C16 C17 C18 -168.30(14) . . . . ? N C16 C17 C23 -49.56(18) . . . . ? N C16 C17 C20 72.96(18) . . . . ? C16 C17 C18 O5 178.09(15) . . . . ? C23 C17 C18 O5 61.27(19) . . . . ? C20 C17 C18 O5 -62.15(19) . . . . ? C18 C17 C20 C21 130.66(17) . . . . ? C16 C17 C20 C21 -111.46(18) . . . . ? C23 C17 C20 C21 8.3(2) . . . . ? C17 C20 C21 C22 49.3(2) . . . . ? C20 C21 C22 O6 70.81(19) . . . . ? C20 C21 C22 C12 -56.4(2) . . . . ? C13 C12 C22 O6 -7.55(19) . . . . ? C10 C12 C22 O6 113.65(15) . . . . ? C23 C12 C22 O6 -120.89(15) . . . . ? C13 C12 C22 C21 119.08(16) . . . . ? C10 C12 C22 C21 -119.72(16) . . . . ? C23 C12 C22 C21 5.7(2) . . . . ? C13 C12 C23 C24 44.46(15) . . . . ? C10 C12 C23 C24 -70.43(17) . . . . ? C22 C12 C23 C24 167.02(14) . . . . ? C13 C12 C23 C17 -72.88(15) . . . . ? C10 C12 C23 C17 172.24(14) . . . . ? C22 C12 C23 C17 49.69(18) . . . . ? C18 C17 C23 C24 69.19(18) . . . . ? C16 C17 C23 C24 -47.71(18) . . . . ? C20 C17 C23 C24 -169.26(15) . . . . ? C18 C17 C23 C12 -178.49(14) . . . . ? C16 C17 C23 C12 64.61(16) . . . . ? C20 C17 C23 C12 -56.93(19) . . . . ? C12 C23 C24 C25 -19.75(16) . . . . ? C17 C23 C24 C25 95.90(16) . . . . ? O4 C8 C25 C13 -178.25(14) . . . . ? C9 C8 C25 C13 64.99(18) . . . . ? C7 C8 C25 C13 -61.12(18) . . . . ? O4 C8 C25 C24 67.69(16) . . . . ? C9 C8 C25 C24 -49.07(16) . . . . ? C7 C8 C25 C24 -175.17(13) . . . . ? N C13 C25 C8 164.88(14) . . . . ? C12 C13 C25 C8 -77.23(16) . . . . ? N C13 C25 C24 -77.27(17) . . . . ? C12 C13 C25 C24 40.63(15) . . . . ? C23 C24 C25 C8 105.68(14) . . . . ? C23 C24 C25 C13 -12.59(16) . . . . ? C15 C14 N C16 167.84(15) . . . . ? C15 C14 N C13 -64.5(2) . . . . ? C17 C16 N C14 176.44(14) . . . . ? C17 C16 N C13 48.93(19) . . . . ? C12 C13 N C14 173.12(13) . . . . ? C25 C13 N C14 -74.03(19) . . . . ? C12 C13 N C16 -61.17(17) . . . . ? C25 C13 N C16 51.7(2) . . . . ? O1 C2 O2 C3 9.4(3) . . . . ? C1 C2 O2 C3 -169.64(16) . . . . ? C4 C3 O2 C2 69.3(2) . . . . ? C9 C3 O2 C2 -177.01(15) . . . . ? C4 C5 O3 C6 -66.7(2) . . . . ? C7 C5 O3 C6 169.14(17) . . . . ? C17 C18 O5 C19 -172.99(16) . . . . ? loop_ _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z -0.0301 -8.4881 0.2304 -0.3733 0.2272 0.8995 -5.7863 -0.0070 0.0922 0.7651 -0.4688 0.4414 -0.8739 8.3894 -0.2134 0.4885 -0.2978 -0.8202 -0.2470 0.3608 6.3607 -0.5220 -0.8529 -0.0090 0.2470 -0.3608 -6.3607 0.5220 0.8529 0.0090 4.4157 -5.4786 0.0746 -0.8273 0.5066 0.2428 5.7644 0.7427 -0.1043 -0.7302 0.4461 -0.5175 3.9410 6.2213 -0.2173 -0.2461 0.1493 -0.9577 2.2891 0.1236 5.6853 -0.8105 -0.5580 -0.1781 -0.6926 -6.5656 4.0095 -0.5426 -0.3724 0.7529 -2.3306 -0.2724 -5.6598 0.8075 0.5560 0.1971 -2.7350 -7.4457 -0.3875 0.0876 0.0616 0.9942 2.6293 7.5615 0.0185 -0.0355 -0.0258 -0.9990 -2.1839 0.4065 6.0244 -0.2309 -0.9638 0.1330 -0.9258 3.8459 5.6350 -0.2197 -0.9192 -0.3267 -0.1308 -5.8676 -4.5809 0.1816 0.7613 0.6225 -0.6690 -3.0108 -5.8513 0.4874 0.7957 0.3596