#------------------------------------------------------------------------------ #$Date: 2020-07-06 05:32:24 +0300 (Mon, 06 Jul 2020) $ #$Revision: 253844 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/79/1557967.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_1557967 loop_ _publ_author_name 'Fairley, Michael' 'Bole, Leonie J.' 'Mulks, Florian F.' 'Main, Laura' 'Kennedy, Alan R.' 'O'Hara, Charles T.' 'Garc\'ia-Alvarez, Joaqu\'in' 'Hevia, Eva' _publ_section_title ; Ultrafast amidation of esters using lithium amides under aerobic ambient temperature conditions in sustainable solvents ; _journal_issue 25 _journal_name_full 'Chemical Science' _journal_page_first 6500 _journal_paper_doi 10.1039/D0SC01349H _journal_volume 11 _journal_year 2020 _chemical_formula_sum 'C32 H52 Li2 N2 O4' _chemical_formula_weight 542.63 _chemical_properties_physical Air-sensitive,Moisture-sensitive,Oxygen-sensitive _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens mixed _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2019-12-20 deposited with the CCDC. 2020-04-30 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 112.088(4) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 9.0773(3) _cell_length_b 20.9604(6) _cell_length_c 9.2929(4) _cell_measurement_reflns_used 2921 _cell_measurement_temperature 123(2) _cell_measurement_theta_max 72.8960 _cell_measurement_theta_min 4.2310 _cell_volume 1638.34(11) _computing_cell_refinement CrysalisPro _computing_data_collection CrysalisPro _computing_data_reduction CrysalisPro _computing_publication_material SHELXL _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution SHELXS _diffrn_ambient_temperature 123(2) _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'Oxford Diffraction Gemini S' _diffrn_measurement_method 'omega scans' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0313 _diffrn_reflns_av_unetI/netI 0.0266 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 7885 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_theta_full 69.985 _diffrn_reflns_theta_max 69.985 _diffrn_reflns_theta_min 4.218 _diffrn_source 'sealed tube' _exptl_absorpt_coefficient_mu 0.547 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.08831 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.100 _exptl_crystal_description fragment _exptl_crystal_F_000 592 _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.4 _refine_diff_density_max 0.846 _refine_diff_density_min -0.573 _refine_diff_density_rms 0.086 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.539 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 215 _refine_ls_number_reflns 3103 _refine_ls_number_restraints 117 _refine_ls_restrained_S_all 1.587 _refine_ls_R_factor_all 0.1170 _refine_ls_R_factor_gt 0.1047 _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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.3328 _refine_ls_wR_factor_ref 0.3569 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2523 _reflns_number_total 3103 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0sc01349h2.cif _cod_data_source_block rmmf2 _cod_depositor_comments 'Adding full bibliography for 1557967--1557970.cif.' _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 1557967 _shelx_shelxl_version_number 2014/7 _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_res_file ; shelx.res created by SHELXL-2014/7 TITL RMMF2 in P2(1)/c CELL 1.54184 9.0773 20.9604 9.2929 90.000 112.088 90.000 ZERR 2.00 0.0003 0.0006 0.0004 0.000 0.004 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC LI O N C H UNIT 4 8 4 64 104 MERG 2 OMIT -3.00 140.00 DFIX 1.43 .01 O2 C12 O2 C15 O1 C10 O1 C10A O2 C1A O2 C15A DFIX 1.53 .01 C13 C12 C14 C13 C15 C14 C15 C16 C10 C11 C10 C9 dfix 1.53 .01 c10a c9a c9a c8 c10a c11a c8 c9 DFIX 1.53 .01 C13a C12a C14a C13a C15a C14a C15a C16a eadp c9 c9a EADP C10 C10A eadp c11 c11a EADP C12 C12A EADP C13 C13A eadp c14 c14a eadp c15 c15a EADP C16 C16A DELU 0.010 0.010 O1 C7 C8 C9 C10 C11 SIMU 0.020 0.020 1.700 O1 C7 C8 C9 C10 C11 DELU 0.010 0.010 O2 C12 C13 C14 C15 C16 SIMU 0.020 0.020 1.700 O2 C12 C13 C14 C15 C16 FMAP 2 PLAN 20 ACTA 140.00 BOND $H CONF L.S. 12 TEMP -150.00 WGHT 0.200000 FVAR 6.89343 0.60933 0.64949 LI1 1 0.401987 0.457018 0.999121 11.00000 0.04008 0.04310 = 0.03780 0.00100 0.01212 0.00023 O1 2 0.193401 0.434775 0.837627 11.00000 0.03757 0.05993 = 0.04421 -0.00621 0.01448 -0.00260 O2 2 0.413230 0.388698 1.147854 11.00000 0.08783 0.04886 = 0.05393 0.01177 0.02585 -0.00498 N1 3 0.582583 0.453016 0.915576 11.00000 0.04095 0.04357 = 0.03881 -0.00215 0.01359 0.00201 C1 4 0.687097 0.403071 0.966419 11.00000 0.03798 0.04163 = 0.05419 -0.00390 0.02129 -0.00373 C2 4 0.709324 0.356083 0.866300 11.00000 0.06360 0.04857 = 0.07059 -0.00810 0.03765 -0.00101 AFIX 43 H2 5 0.650081 0.358702 0.757703 11.00000 -1.20000 AFIX 0 C3 4 0.816554 0.306294 0.924925 11.00000 0.08816 0.05020 = 0.12511 -0.00976 0.06830 0.00709 AFIX 43 H3 5 0.829937 0.275781 0.855228 11.00000 -1.20000 AFIX 0 C4 4 0.904089 0.300162 1.082161 11.00000 0.06283 0.05087 = 0.14000 0.01752 0.04345 0.01924 AFIX 43 H4 5 0.975303 0.265462 1.121372 11.00000 -1.20000 AFIX 0 C5 4 0.885237 0.345448 1.179567 11.00000 0.04892 0.05914 = 0.08937 0.01860 0.01088 0.00471 AFIX 43 H5 5 0.946243 0.342277 1.287710 11.00000 -1.20000 AFIX 0 C6 4 0.780166 0.395778 1.125795 11.00000 0.04328 0.04866 = 0.05865 0.00282 0.01466 0.00090 AFIX 43 H6 5 0.770487 0.426080 1.197757 11.00000 -1.20000 AFIX 0 C7 4 0.063899 0.453360 0.883479 11.00000 0.03713 0.06444 = 0.05461 -0.00319 0.02017 -0.00469 AFIX 23 H7A 5 0.092731 0.491565 0.951015 11.00000 -1.20000 H7B 5 0.036141 0.418305 0.940112 11.00000 -1.20000 AFIX 0 C8 4 -0.072932 0.467731 0.733310 11.00000 0.04012 0.07018 = 0.06590 0.00719 0.01829 0.00141 AFIX 23 H8A 5 -0.073806 0.513300 0.704980 11.00000 -1.20000 H8B 5 -0.175967 0.456904 0.740807 11.00000 -1.20000 AFIX 0 PART 1 C9 4 -0.040132 0.425106 0.616057 21.00000 0.04451 0.08981 = 0.04846 -0.00141 0.00908 -0.00342 AFIX 23 H9A 5 -0.087291 0.443107 0.509972 21.00000 -1.20000 H9B 5 -0.082534 0.381579 0.615897 21.00000 -1.20000 AFIX 0 C10 4 0.140740 0.424662 0.674390 21.00000 0.04430 0.05812 = 0.04507 -0.00555 0.01400 -0.00594 AFIX 13 H10 5 0.176287 0.461390 0.626770 21.00000 -1.20000 AFIX 0 C11 4 0.213391 0.363973 0.642037 21.00000 0.05563 0.07329 = 0.06541 -0.02514 0.01163 -0.00166 AFIX 137 H11A 5 0.329515 0.367790 0.684780 21.00000 -1.50000 H11B 5 0.175927 0.357060 0.529644 21.00000 -1.50000 H11C 5 0.181753 0.327787 0.690747 21.00000 -1.50000 AFIX 0 C12 4 0.412023 0.326473 1.081587 31.00000 0.11110 0.05137 = 0.07744 0.00085 0.03467 -0.03540 AFIX 23 H12A 5 0.500754 0.322494 1.044761 31.00000 -1.20000 H12B 5 0.310745 0.319449 0.992470 31.00000 -1.20000 AFIX 0 C13 4 0.429868 0.279468 1.205257 31.00000 0.20283 0.06374 = 0.13297 0.02472 0.05880 0.00448 AFIX 23 H13A 5 0.357641 0.242818 1.163171 31.00000 -1.20000 H13B 5 0.540515 0.263448 1.249637 31.00000 -1.20000 AFIX 0 C14 4 0.390319 0.311761 1.322154 31.00000 0.13340 0.08040 = 0.09056 0.03720 0.05349 0.01215 AFIX 23 H14A 5 0.468672 0.301567 1.427033 31.00000 -1.20000 H14B 5 0.283294 0.298965 1.316495 31.00000 -1.20000 AFIX 0 C15 4 0.393999 0.381387 1.288621 31.00000 0.09825 0.09686 = 0.06412 0.01344 0.04667 -0.00477 AFIX 13 H15 5 0.282684 0.396037 1.266085 31.00000 -1.20000 AFIX 0 C16 4 0.494563 0.431226 1.394330 31.00000 0.07934 0.11781 = 0.07130 0.01310 0.03836 0.00459 AFIX 137 H16A 5 0.592560 0.436695 1.374632 31.00000 -1.50000 H16B 5 0.521142 0.418124 1.502424 31.00000 -1.50000 H16C 5 0.436203 0.471676 1.375538 31.00000 -1.50000 AFIX 0 PART 2 C9A 4 -0.050273 0.415356 0.628903 -21.00000 0.04451 0.08981 = 0.04846 -0.00141 0.00908 -0.00342 AFIX 23 H9A1 5 -0.128529 0.380662 0.614606 -21.00000 -1.20000 H9A2 5 -0.063712 0.432841 0.525753 -21.00000 -1.20000 AFIX 0 C10A 4 0.118833 0.390540 0.712248 -21.00000 0.04430 0.05812 = 0.04507 -0.00555 0.01400 -0.00594 AFIX 13 H10A 5 0.115928 0.346969 0.754939 -21.00000 -1.20000 AFIX 0 C11A 4 0.217990 0.389582 0.612575 -21.00000 0.05563 0.07329 = 0.06541 -0.02514 0.01163 -0.00166 AFIX 137 H11D 5 0.209211 0.430873 0.560520 -21.00000 -1.50000 H11E 5 0.179445 0.355760 0.534509 -21.00000 -1.50000 H11F 5 0.329453 0.381495 0.678223 -21.00000 -1.50000 AFIX 0 C15A 4 0.502804 0.390326 1.311754 -31.00000 0.09825 0.09686 = 0.06412 0.01344 0.04667 -0.00477 AFIX 13 H15A 5 0.603390 0.413849 1.326879 -31.00000 -1.20000 AFIX 0 C16A 4 0.420227 0.427142 1.396233 -31.00000 0.07934 0.11781 = 0.07130 0.01310 0.03836 0.00459 AFIX 137 H16D 5 0.367390 0.464274 1.334166 -31.00000 -1.50000 H16E 5 0.498055 0.441496 1.496310 -31.00000 -1.50000 H16F 5 0.340877 0.399893 1.413836 -31.00000 -1.50000 AFIX 0 C14A 4 0.549344 0.322059 1.357828 -31.00000 0.13340 0.08040 = 0.09056 0.03720 0.05349 0.01215 AFIX 23 H14C 5 0.482753 0.303704 1.410846 -31.00000 -1.20000 H14D 5 0.662318 0.319395 1.428603 -31.00000 -1.20000 AFIX 0 C13A 4 0.522368 0.286600 1.206861 -31.00000 0.20283 0.06374 = 0.13297 0.02472 0.05880 0.00448 AFIX 23 H13C 5 0.618462 0.289735 1.181045 -31.00000 -1.20000 H13D 5 0.501633 0.240927 1.218854 -31.00000 -1.20000 AFIX 0 C12A 4 0.382601 0.315511 1.078739 -31.00000 0.11110 0.05137 = 0.07744 0.00085 0.03467 -0.03540 AFIX 23 H12C 5 0.279794 0.297806 1.074082 -31.00000 -1.20000 H12D 5 0.391155 0.311911 0.975941 -31.00000 -1.20000 AFIX 0 PART 0 H1 5 0.533550 0.452672 0.812450 11.00000 0.04397 HKLF 4 REM RMMF2 in P2(1)/c REM R1 = 0.1047 for 2523 Fo > 4sig(Fo) and 0.1170 for all 3103 data REM 215 parameters refined using 117 restraints END WGHT 0.2000 0.0000 REM Highest difference peak 0.846, deepest hole -0.573, 1-sigma level 0.086 Q1 1 0.3542 0.3317 1.1599 11.00000 0.05 0.85 Q2 1 0.5246 0.3477 1.4129 11.00000 0.05 0.78 Q3 1 0.3354 0.2818 1.1319 11.00000 0.05 0.61 Q4 1 0.4233 0.2881 1.0643 11.00000 0.05 0.56 Q5 1 0.6215 0.4218 0.9422 11.00000 0.05 0.31 Q6 1 0.8535 0.3018 1.0166 11.00000 0.05 0.30 Q7 1 0.4503 0.2936 1.2646 11.00000 0.05 0.30 Q8 1 -0.0220 0.4569 0.8131 11.00000 0.05 0.27 Q9 1 0.6110 0.4854 0.9756 11.00000 0.05 0.27 Q10 1 -0.0727 0.4399 0.6886 11.00000 0.05 0.26 Q11 1 0.1568 0.3867 0.6755 11.00000 0.05 0.25 Q12 1 0.2166 0.4167 0.9225 11.00000 0.05 0.19 Q13 1 0.1466 0.3944 0.8030 11.00000 0.05 0.19 Q14 1 0.0260 0.4175 0.6359 11.00000 0.05 0.19 Q15 1 0.1227 0.4676 0.9916 11.00000 0.05 0.18 Q16 1 0.4497 0.2376 1.2415 11.00000 0.05 0.17 Q17 1 0.0576 0.4096 0.8930 11.00000 0.05 0.17 Q18 1 0.8089 0.4285 1.1475 11.00000 0.05 0.15 Q19 1 0.1633 0.3318 0.6213 11.00000 0.05 0.14 Q20 1 0.5812 0.3592 1.5363 11.00000 0.05 0.13 ; _shelx_res_checksum 12196 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' 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 Li1 Li 0.4020(5) 0.4570(2) 0.9991(5) 0.0411(9) Uani 1 1 d . . . . . O1 O 0.1934(2) 0.43477(10) 0.8376(2) 0.0475(6) Uani 1 1 d D U . . . O2 O 0.4132(3) 0.38870(10) 1.1479(3) 0.0638(7) Uani 1 1 d D U . . . N1 N 0.5826(2) 0.45302(10) 0.9156(2) 0.0415(6) Uani 1 1 d . . . . . C1 C 0.6871(3) 0.40307(12) 0.9664(3) 0.0434(7) Uani 1 1 d . . . . . C2 C 0.7093(4) 0.35608(15) 0.8663(4) 0.0573(8) Uani 1 1 d . . . . . H2 H 0.6501 0.3587 0.7577 0.069 Uiso 1 1 calc R U . . . C3 C 0.8166(5) 0.30629(17) 0.9249(6) 0.0796(13) Uani 1 1 d . . . . . H3 H 0.8299 0.2758 0.8552 0.096 Uiso 1 1 calc R U . . . C4 C 0.9041(5) 0.30016(18) 1.0822(6) 0.0830(13) Uani 1 1 d . . . . . H4 H 0.9753 0.2655 1.1214 0.100 Uiso 1 1 calc R U . . . C5 C 0.8852(4) 0.34545(18) 1.1796(5) 0.0702(10) Uani 1 1 d . . . . . H5 H 0.9462 0.3423 1.2877 0.084 Uiso 1 1 calc R U . . . C6 C 0.7802(3) 0.39578(14) 1.1258(4) 0.0515(8) Uani 1 1 d . . . . . H6 H 0.7705 0.4261 1.1978 0.062 Uiso 1 1 calc R U . . . C7 C 0.0639(3) 0.45336(15) 0.8835(3) 0.0512(8) Uani 1 1 d . U . . . H7A H 0.0927 0.4916 0.9510 0.061 Uiso 1 1 calc R U . . . H7B H 0.0361 0.4183 0.9401 0.061 Uiso 1 1 calc R U . . . C8 C -0.0729(3) 0.46773(17) 0.7333(4) 0.0592(8) Uani 1 1 d D U . . . H8A H -0.0738 0.5133 0.7050 0.071 Uiso 1 1 calc R U . A 1 H8B H -0.1760 0.4569 0.7408 0.071 Uiso 1 1 calc R U . A 1 C9 C -0.0401(10) 0.4251(8) 0.6161(15) 0.063(3) Uani 0.609(6) 1 d D U P B 1 H9A H -0.0873 0.4431 0.5100 0.076 Uiso 0.609(6) 1 calc R U P B 1 H9B H -0.0825 0.3816 0.6159 0.076 Uiso 0.609(6) 1 calc R U P B 1 C10 C 0.1407(5) 0.4247(2) 0.6744(5) 0.0500(10) Uani 0.609(6) 1 d D U P B 1 H10 H 0.1763 0.4614 0.6268 0.060 Uiso 0.609(6) 1 calc R U P B 1 C11 C 0.2134(11) 0.3640(3) 0.6420(11) 0.068(2) Uani 0.609(6) 1 d D U P B 1 H11A H 0.3295 0.3678 0.6848 0.102 Uiso 0.609(6) 1 calc R U P B 1 H11B H 0.1759 0.3571 0.5296 0.102 Uiso 0.609(6) 1 calc R U P B 1 H11C H 0.1818 0.3278 0.6907 0.102 Uiso 0.609(6) 1 calc R U P B 1 C12 C 0.4120(14) 0.3265(4) 1.0816(13) 0.080(2) Uani 0.649(5) 1 d D U P C 1 H12A H 0.5008 0.3225 1.0448 0.096 Uiso 0.649(5) 1 calc R U P C 1 H12B H 0.3107 0.3194 0.9925 0.096 Uiso 0.649(5) 1 calc R U P C 1 C13 C 0.4299(18) 0.2795(4) 1.2053(12) 0.134(4) Uani 0.649(5) 1 d D U P C 1 H13A H 0.3576 0.2428 1.1632 0.161 Uiso 0.649(5) 1 calc R U P C 1 H13B H 0.5405 0.2634 1.2496 0.161 Uiso 0.649(5) 1 calc R U P C 1 C14 C 0.3903(11) 0.3118(3) 1.3222(9) 0.098(2) Uani 0.649(5) 1 d D U P C 1 H14A H 0.4687 0.3016 1.4270 0.118 Uiso 0.649(5) 1 calc R U P C 1 H14B H 0.2833 0.2990 1.3165 0.118 Uiso 0.649(5) 1 calc R U P C 1 C15 C 0.3940(9) 0.3814(3) 1.2886(6) 0.0817(15) Uani 0.649(5) 1 d D U P C 1 H15 H 0.2827 0.3960 1.2661 0.098 Uiso 0.649(5) 1 calc R U P C 1 C16 C 0.4946(10) 0.4312(4) 1.3943(8) 0.0866(18) Uani 0.649(5) 1 d D U P C 1 H16A H 0.5926 0.4367 1.3746 0.130 Uiso 0.649(5) 1 calc R U P C 1 H16B H 0.5211 0.4181 1.5024 0.130 Uiso 0.649(5) 1 calc R U P C 1 H16C H 0.4362 0.4717 1.3755 0.130 Uiso 0.649(5) 1 calc R U P C 1 C9A C -0.0503(17) 0.4154(13) 0.629(3) 0.063(3) Uani 0.391(6) 1 d D . P B 2 H9A1 H -0.1285 0.3807 0.6146 0.076 Uiso 0.391(6) 1 calc R U P B 2 H9A2 H -0.0637 0.4328 0.5258 0.076 Uiso 0.391(6) 1 calc R U P B 2 C10A C 0.1188(8) 0.3905(4) 0.7122(8) 0.0500(10) Uani 0.391(6) 1 d D . P B 2 H10A H 0.1159 0.3470 0.7549 0.060 Uiso 0.391(6) 1 calc R U P B 2 C11A C 0.2180(19) 0.3896(6) 0.6126(18) 0.068(2) Uani 0.391(6) 1 d D . P B 2 H11D H 0.2092 0.4309 0.5605 0.102 Uiso 0.391(6) 1 calc R U P B 2 H11E H 0.1794 0.3558 0.5345 0.102 Uiso 0.391(6) 1 calc R U P B 2 H11F H 0.3295 0.3815 0.6782 0.102 Uiso 0.391(6) 1 calc R U P B 2 C15A C 0.5028(15) 0.3903(5) 1.3118(9) 0.0817(15) Uani 0.351(5) 1 d D . P C 2 H15A H 0.6034 0.4138 1.3269 0.098 Uiso 0.351(5) 1 calc R U P C 2 C16A C 0.4202(19) 0.4271(8) 1.3962(17) 0.0866(18) Uani 0.351(5) 1 d D . P C 2 H16D H 0.3674 0.4643 1.3342 0.130 Uiso 0.351(5) 1 calc R U P C 2 H16E H 0.4981 0.4415 1.4963 0.130 Uiso 0.351(5) 1 calc R U P C 2 H16F H 0.3409 0.3999 1.4138 0.130 Uiso 0.351(5) 1 calc R U P C 2 C14A C 0.549(2) 0.3221(5) 1.3578(16) 0.098(2) Uani 0.351(5) 1 d D . P C 2 H14C H 0.4828 0.3037 1.4108 0.118 Uiso 0.351(5) 1 calc R U P C 2 H14D H 0.6623 0.3194 1.4286 0.118 Uiso 0.351(5) 1 calc R U P C 2 C13A C 0.522(3) 0.2866(9) 1.2069(19) 0.134(4) Uani 0.351(5) 1 d D . P C 2 H13C H 0.6185 0.2897 1.1810 0.161 Uiso 0.351(5) 1 calc R U P C 2 H13D H 0.5016 0.2409 1.2189 0.161 Uiso 0.351(5) 1 calc R U P C 2 C12A C 0.383(3) 0.3155(10) 1.079(3) 0.080(2) Uani 0.351(5) 1 d D . P C 2 H12C H 0.2798 0.2978 1.0741 0.096 Uiso 0.351(5) 1 calc R U P C 2 H12D H 0.3912 0.3119 0.9759 0.096 Uiso 0.351(5) 1 calc R U P C 2 H1 H 0.534(4) 0.4527(15) 0.812(4) 0.044(8) 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 Li1 0.040(2) 0.043(2) 0.0378(18) 0.0010(16) 0.0121(15) 0.0002(16) O1 0.0376(10) 0.0599(12) 0.0442(10) -0.0062(8) 0.0145(8) -0.0026(8) O2 0.0878(17) 0.0489(12) 0.0539(12) 0.0118(9) 0.0259(11) -0.0050(10) N1 0.0410(11) 0.0436(13) 0.0388(11) -0.0022(8) 0.0136(8) 0.0020(8) C1 0.0380(12) 0.0416(13) 0.0542(15) -0.0039(10) 0.0213(11) -0.0037(10) C2 0.0636(18) 0.0486(16) 0.0706(18) -0.0081(13) 0.0376(15) -0.0010(13) C3 0.088(3) 0.0502(18) 0.125(4) -0.010(2) 0.068(3) 0.0071(17) C4 0.063(2) 0.051(2) 0.140(4) 0.018(2) 0.043(2) 0.0192(15) C5 0.0489(17) 0.0591(19) 0.089(2) 0.0186(17) 0.0109(16) 0.0047(14) C6 0.0433(14) 0.0487(15) 0.0586(16) 0.0028(12) 0.0147(12) 0.0009(11) C7 0.0371(13) 0.0644(18) 0.0546(15) -0.0032(12) 0.0202(11) -0.0047(12) C8 0.0401(14) 0.0702(19) 0.0659(18) 0.0072(14) 0.0183(12) 0.0014(13) C9 0.0445(18) 0.090(5) 0.048(2) -0.001(3) 0.0091(17) -0.003(3) C10 0.0443(19) 0.058(3) 0.045(2) -0.0056(18) 0.0140(14) -0.0059(19) C11 0.056(2) 0.073(5) 0.065(4) -0.025(4) 0.012(2) -0.002(4) C12 0.111(5) 0.051(4) 0.077(2) 0.001(2) 0.035(3) -0.035(4) C13 0.203(11) 0.064(4) 0.133(5) 0.025(3) 0.059(6) 0.004(6) C14 0.133(5) 0.080(3) 0.091(4) 0.037(3) 0.053(4) 0.012(4) C15 0.098(4) 0.097(3) 0.064(3) 0.013(2) 0.047(3) -0.005(3) C16 0.079(5) 0.118(4) 0.071(3) 0.013(3) 0.038(4) 0.005(4) C9A 0.0445(18) 0.090(5) 0.048(2) -0.001(3) 0.0091(17) -0.003(3) C10A 0.0443(19) 0.058(3) 0.045(2) -0.0056(18) 0.0140(14) -0.0059(19) C11A 0.056(2) 0.073(5) 0.065(4) -0.025(4) 0.012(2) -0.002(4) C15A 0.098(4) 0.097(3) 0.064(3) 0.013(2) 0.047(3) -0.005(3) C16A 0.079(5) 0.118(4) 0.071(3) 0.013(3) 0.038(4) 0.005(4) C14A 0.133(5) 0.080(3) 0.091(4) 0.037(3) 0.053(4) 0.012(4) C13A 0.203(11) 0.064(4) 0.133(5) 0.025(3) 0.059(6) 0.004(6) C12A 0.111(5) 0.051(4) 0.077(2) 0.001(2) 0.035(3) -0.035(4) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Li Li 0.0008 0.0003 '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' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' 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 O2 Li1 O1 98.2(2) . . ? O2 Li1 N1 115.1(2) . 3_667 ? O1 Li1 N1 114.9(2) . 3_667 ? O2 Li1 N1 113.4(2) . . ? O1 Li1 N1 112.0(2) . . ? N1 Li1 N1 103.7(2) 3_667 . ? O2 Li1 Li1 131.6(3) . 3_667 ? O1 Li1 Li1 130.0(3) . 3_667 ? N1 Li1 Li1 52.43(16) 3_667 3_667 ? N1 Li1 Li1 51.27(16) . 3_667 ? C10 O1 C7 111.7(2) . . ? C10A O1 C7 103.0(3) . . ? C10 O1 Li1 133.2(3) . . ? C10A O1 Li1 142.0(3) . . ? C7 O1 Li1 111.4(2) . . ? C15 O2 C12 108.6(5) . . ? C15A O2 C12A 112.5(9) . . ? C15 O2 Li1 138.5(3) . . ? C15A O2 Li1 126.1(5) . . ? C12 O2 Li1 111.6(4) . . ? C12A O2 Li1 116.6(9) . . ? C1 N1 Li1 129.6(2) . 3_667 ? C1 N1 Li1 116.5(2) . . ? Li1 N1 Li1 76.3(2) 3_667 . ? C1 N1 H1 111(2) . . ? Li1 N1 H1 111(2) 3_667 . ? Li1 N1 H1 105(2) . . ? N1 C1 C6 120.5(2) . . ? N1 C1 C2 123.6(3) . . ? C6 C1 C2 115.9(3) . . ? C3 C2 C1 121.0(4) . . ? C3 C2 H2 119.5 . . ? C1 C2 H2 119.5 . . ? C4 C3 C2 121.6(4) . . ? C4 C3 H3 119.2 . . ? C2 C3 H3 119.2 . . ? C5 C4 C3 118.1(3) . . ? C5 C4 H4 121.0 . . ? C3 C4 H4 121.0 . . ? C4 C5 C6 122.1(4) . . ? C4 C5 H5 118.9 . . ? C6 C5 H5 118.9 . . ? C5 C6 C1 121.4(3) . . ? C5 C6 H6 119.3 . . ? C1 C6 H6 119.3 . . ? O1 C7 C8 105.0(2) . . ? O1 C7 H7A 110.7 . . ? C8 C7 H7A 110.7 . . ? O1 C7 H7B 110.7 . . ? C8 C7 H7B 110.7 . . ? H7A C7 H7B 108.8 . . ? C7 C8 C9 103.3(5) . . ? C7 C8 C9A 100.6(7) . . ? C7 C8 H8A 111.1 . . ? C9 C8 H8A 111.1 . . ? C7 C8 H8B 111.1 . . ? C9 C8 H8B 111.1 . . ? H8A C8 H8B 109.1 . . ? C8 C9 C10 102.9(5) . . ? C8 C9 H9A 111.2 . . ? C10 C9 H9A 111.2 . . ? C8 C9 H9B 111.2 . . ? C10 C9 H9B 111.2 . . ? H9A C9 H9B 109.1 . . ? O1 C10 C11 109.9(5) . . ? O1 C10 C9 105.3(5) . . ? C11 C10 C9 115.2(6) . . ? O1 C10 H10 108.8 . . ? C11 C10 H10 108.8 . . ? C9 C10 H10 108.8 . . ? 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 . . ? O2 C12 C13 106.9(8) . . ? O2 C12 H12A 110.3 . . ? C13 C12 H12A 110.3 . . ? O2 C12 H12B 110.3 . . ? C13 C12 H12B 110.3 . . ? H12A C12 H12B 108.6 . . ? C14 C13 C12 106.8(8) . . ? C14 C13 H13A 110.4 . . ? C12 C13 H13A 110.4 . . ? C14 C13 H13B 110.4 . . ? C12 C13 H13B 110.4 . . ? H13A C13 H13B 108.6 . . ? C13 C14 C15 105.7(6) . . ? C13 C14 H14A 110.6 . . ? C15 C14 H14A 110.6 . . ? C13 C14 H14B 110.6 . . ? C15 C14 H14B 110.6 . . ? H14A C14 H14B 108.7 . . ? O2 C15 C16 106.3(5) . . ? O2 C15 C14 108.9(5) . . ? C16 C15 C14 127.1(7) . . ? O2 C15 H15 104.1 . . ? C16 C15 H15 104.1 . . ? C14 C15 H15 104.1 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C10A C9A C8 105.8(8) . . ? C10A C9A H9A1 110.6 . . ? C8 C9A H9A1 110.6 . . ? C10A C9A H9A2 110.6 . . ? C8 C9A H9A2 110.6 . . ? H9A1 C9A H9A2 108.7 . . ? O1 C10A C11A 107.2(8) . . ? O1 C10A C9A 105.5(6) . . ? C11A C10A C9A 114.2(14) . . ? O1 C10A H10A 109.9 . . ? C11A C10A H10A 109.9 . . ? C9A C10A H10A 109.9 . . ? C10A C11A H11D 109.5 . . ? C10A C11A H11E 109.5 . . ? H11D C11A H11E 109.5 . . ? C10A C11A H11F 109.5 . . ? H11D C11A H11F 109.5 . . ? H11E C11A H11F 109.5 . . ? O2 C15A C16A 112.1(10) . . ? O2 C15A C14A 105.4(9) . . ? C16A C15A C14A 119.0(11) . . ? O2 C15A H15A 106.5 . . ? C16A C15A H15A 106.5 . . ? C14A C15A H15A 106.5 . . ? C15A C16A H16D 109.5 . . ? C15A C16A H16E 109.5 . . ? H16D C16A H16E 109.5 . . ? C15A C16A H16F 109.5 . . ? H16D C16A H16F 109.5 . . ? H16E C16A H16F 109.5 . . ? C15A C14A C13A 105.7(11) . . ? C15A C14A H14C 110.6 . . ? C13A C14A H14C 110.6 . . ? C15A C14A H14D 110.6 . . ? C13A C14A H14D 110.6 . . ? H14C C14A H14D 108.7 . . ? C12A C13A C14A 109.2(18) . . ? C12A C13A H13C 109.8 . . ? C14A C13A H13C 109.8 . . ? C12A C13A H13D 109.8 . . ? C14A C13A H13D 109.8 . . ? H13C C13A H13D 108.3 . . ? C13A C12A O2 95.6(15) . . ? C13A C12A H12C 112.6 . . ? O2 C12A H12C 112.6 . . ? C13A C12A H12D 112.6 . . ? O2 C12A H12D 112.6 . . ? H12C C12A H12D 110.1 . . ? 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 Li1 O2 1.966(5) . ? Li1 O1 1.979(4) . ? Li1 N1 2.030(5) 3_667 ? Li1 N1 2.063(5) . ? Li1 Li1 2.528(8) 3_667 ? O1 C10 1.425(4) . ? O1 C10A 1.443(6) . ? O1 C7 1.446(3) . ? O2 C15 1.392(5) . ? O2 C15A 1.432(8) . ? O2 C12 1.441(9) . ? O2 C12A 1.65(2) . ? N1 C1 1.372(3) . ? N1 Li1 2.030(5) 3_667 ? N1 H1 0.89(3) . ? C1 C6 1.411(4) . ? C1 C2 1.420(4) . ? C2 C3 1.391(5) . ? C2 H2 0.9500 . ? C3 C4 1.382(7) . ? C3 H3 0.9500 . ? C4 C5 1.366(7) . ? C4 H4 0.9500 . ? C5 C6 1.383(5) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.509(4) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.523(7) . ? C8 C9A 1.529(9) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.523(8) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.514(7) . ? C10 H10 1.0000 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C13 1.476(8) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.435(8) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.495(7) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.488(8) . ? C15 H15 1.0000 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C9A C10A 1.527(10) . ? C9A H9A1 0.9900 . ? C9A H9A2 0.9900 . ? C10A C11A 1.515(9) . ? C10A H10A 1.0000 . ? C11A H11D 0.9800 . ? C11A H11E 0.9800 . ? C11A H11F 0.9800 . ? C15A C16A 1.489(9) . ? C15A C14A 1.508(9) . ? C15A H15A 1.0000 . ? C16A H16D 0.9800 . ? C16A H16E 0.9800 . ? C16A H16F 0.9800 . ? C14A C13A 1.524(10) . ? C14A H14C 0.9900 . ? C14A H14D 0.9900 . ? C13A C12A 1.503(10) . ? C13A H13C 0.9900 . ? C13A H13D 0.9900 . ? C12A H12C 0.9900 . ? C12A H12D 0.9900 . ? 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 Li1 N1 C1 C6 32.6(4) 3_667 . . . ? Li1 N1 C1 C6 -61.3(3) . . . . ? Li1 N1 C1 C2 -147.5(3) 3_667 . . . ? Li1 N1 C1 C2 118.6(3) . . . . ? N1 C1 C2 C3 -179.6(3) . . . . ? C6 C1 C2 C3 0.3(4) . . . . ? C1 C2 C3 C4 0.7(6) . . . . ? C2 C3 C4 C5 -1.4(6) . . . . ? C3 C4 C5 C6 1.2(6) . . . . ? C4 C5 C6 C1 -0.3(5) . . . . ? N1 C1 C6 C5 179.4(3) . . . . ? C2 C1 C6 C5 -0.4(4) . . . . ? C10 O1 C7 C8 -11.2(4) . . . . ? C10A O1 C7 C8 -46.4(4) . . . . ? Li1 O1 C7 C8 150.1(2) . . . . ? O1 C7 C8 C9 28.3(8) . . . . ? O1 C7 C8 C9A 38.2(14) . . . . ? C7 C8 C9 C10 -34.3(12) . . . . ? C7 O1 C10 C11 -135.4(5) . . . . ? Li1 O1 C10 C11 68.8(6) . . . . ? C7 O1 C10 C9 -10.8(8) . . . . ? Li1 O1 C10 C9 -166.6(7) . . . . ? C8 C9 C10 O1 27.9(12) . . . . ? C8 C9 C10 C11 149.1(8) . . . . ? C15 O2 C12 C13 -13.4(11) . . . . ? Li1 O2 C12 C13 176.9(8) . . . . ? O2 C12 C13 C14 18.1(13) . . . . ? C12 C13 C14 C15 -15.6(13) . . . . ? C12 O2 C15 C16 143.6(7) . . . . ? Li1 O2 C15 C16 -50.9(9) . . . . ? C12 O2 C15 C14 3.7(9) . . . . ? Li1 O2 C15 C14 169.2(5) . . . . ? C13 C14 C15 O2 7.6(11) . . . . ? C13 C14 C15 C16 -121.5(9) . . . . ? C7 C8 C9A C10A -16(2) . . . . ? C7 O1 C10A C11A 156.4(7) . . . . ? Li1 O1 C10A C11A -49.0(11) . . . . ? C7 O1 C10A C9A 34.3(15) . . . . ? Li1 O1 C10A C9A -171.1(15) . . . . ? C8 C9A C10A O1 -10(2) . . . . ? C8 C9A C10A C11A -127.8(17) . . . . ? C12A O2 C15A C16A -125.8(14) . . . . ? Li1 O2 C15A C16A 79.9(12) . . . . ? C12A O2 C15A C14A 5.1(15) . . . . ? Li1 O2 C15A C14A -149.2(8) . . . . ? O2 C15A C14A C13A 15.8(18) . . . . ? C16A C15A C14A C13A 142.6(15) . . . . ? C15A C14A C13A C12A -33(2) . . . . ? C14A C13A C12A O2 33(2) . . . . ? C15A O2 C12A C13A -23.5(18) . . . . ? Li1 O2 C12A C13A 133.4(13) . . . . ?