#------------------------------------------------------------------------------ #$Date: 2020-05-01 01:18:06 +0300 (Fri, 01 May 2020) $ #$Revision: 251334 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/79/1557970.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_1557970 loop_ _publ_author_name 'Fairley, Michael' 'Bole, Leonie' 'Mulks, Florian' 'Main, Laura' 'Kennedy, Alan' '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_name_full 'Chemical Science' _journal_paper_doi 10.1039/D0SC01349H _journal_year 2020 _chemical_formula_moiety 'C42 H42 Li2 N4 O2' _chemical_formula_sum 'C42 H42 Li2 N4 O2' _chemical_formula_weight 648.67 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens geom _audit_creation_date 2020-03-03 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2020-03-03 deposited with the CCDC. 2020-04-30 downloaded from the CCDC. ; _cell_angle_alpha 105.659(2) _cell_angle_beta 94.8850(10) _cell_angle_gamma 95.340(2) _cell_formula_units_Z 1 _cell_length_a 9.5878(2) _cell_length_b 9.9347(2) _cell_length_c 9.9435(2) _cell_measurement_reflns_used 8515 _cell_measurement_temperature 173.01(10) _cell_measurement_theta_max 76.5010 _cell_measurement_theta_min 4.6420 _cell_volume 902.00(3) _computing_cell_refinement 'CrysAlisPro 1.171.41.54a (Rigaku OD, 2020)' _computing_data_collection 'CrysAlisPro 1.171.41.54a (Rigaku OD, 2020)' _computing_data_reduction 'CrysAlisPro 1.171.41.54a (Rigaku OD, 2020)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_temperature 173.15 _diffrn_detector_area_resol_mean 10.0000 _diffrn_detector_type HyPix _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.977 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -31.00 56.00 0.50 0.10 -- -18.75 29.00 40.00 174 2 \w 36.00 122.00 0.50 0.10 -- 47.95 29.00 40.00 172 3 \w -26.00 31.00 0.50 0.10 -- 47.95 -29.00-120.00 114 4 \w 95.00 171.00 0.50 0.30 -- 107.11 29.00 40.00 152 5 \w -92.00 -6.00 0.50 0.10 -- -18.75 -29.00-120.00 172 6 \w -23.00 71.00 0.50 0.10 -- 47.95 -77.00 -30.00 188 7 \w -26.00 23.00 0.50 0.10 -- 47.95 -19.00 -60.00 98 8 \w -26.00 23.00 0.50 0.10 -- 47.95 -19.00 60.00 98 9 \w -26.00 23.00 0.50 0.10 -- 47.95 -19.00-180.00 98 10 \w -25.00 40.00 0.50 0.10 -- 47.95 -38.00-150.00 130 11 \w 35.00 96.00 0.50 0.10 -- 47.95-125.00 120.00 122 12 \w 35.00 68.00 0.50 0.30 -- 107.11 -61.00-180.00 66 13 \w 94.00 171.00 0.50 0.30 -- 107.11 15.00-150.00 154 14 \w 35.00 106.00 0.50 0.30 -- 107.11 -94.00 120.00 142 15 \w 35.00 106.00 0.50 0.30 -- 107.11 -94.00 -30.00 142 16 \w 35.00 106.00 0.50 0.30 -- 107.11 -94.00-120.00 142 17 \w 94.00 171.00 0.50 0.30 -- 107.11 15.00 120.00 154 18 \w 95.00 171.00 0.50 0.30 -- 107.11 125.00 -90.00 152 19 \w 35.00 68.00 0.50 0.30 -- 107.11 -61.00-150.00 66 20 \w 95.00 171.00 0.50 0.30 -- 107.11 30.00 60.00 152 21 \w 35.00 68.00 0.50 0.30 -- 107.11 -61.00 -60.00 66 22 \w 35.00 106.00 0.50 0.30 -- 107.11 -94.00 0.00 142 23 \w 35.00 102.00 0.50 0.30 -- 107.11 -77.00 120.00 134 24 \w 95.00 171.00 0.50 0.30 -- 107.11 45.00 150.00 152 25 \w 35.00 112.00 0.50 0.30 -- 107.11-125.00 -30.00 154 26 \w 35.00 112.00 0.50 0.30 -- 107.11-125.00 30.00 154 27 \w 35.00 68.00 0.50 0.30 -- 107.11 -61.00 150.00 66 28 \w 35.00 106.00 0.50 0.30 -- 107.11 -94.00 90.00 142 29 \w 95.00 171.00 0.50 0.30 -- 107.11 125.00-180.00 152 30 \w 35.00 106.00 0.50 0.30 -- 107.11 -94.00-180.00 142 31 \w 95.00 171.00 0.50 0.30 -- 107.11 45.00 -60.00 152 32 \w 35.00 68.00 0.50 0.30 -- 107.11 -61.00 30.00 66 33 \w 35.00 68.00 0.50 0.30 -- 107.11 -61.00-120.00 66 34 \w 26.00 120.00 0.50 0.10 -- 47.95 77.00 -90.00 188 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy, Dualflex, HyPix' _diffrn_measurement_method '\w scans' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0306 _diffrn_reflns_av_unetI/netI 0.0284 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.977 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 13770 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.977 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 76.951 _diffrn_reflns_theta_min 4.649 _exptl_absorpt_coefficient_mu 0.567 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.59992 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.41.54a (Rigaku Oxford Diffraction, 2020) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.194 _exptl_crystal_description plate _exptl_crystal_F_000 344 _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.075 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.185 _refine_diff_density_min -0.208 _refine_diff_density_rms 0.039 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 228 _refine_ls_number_reflns 3722 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.065 _refine_ls_R_factor_all 0.0462 _refine_ls_R_factor_gt 0.0393 _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^)+(0.0523P)^2^+0.1719P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1038 _refine_ls_wR_factor_ref 0.1120 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3222 _reflns_number_total 3722 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0sc01349h2.cif _cod_data_source_block 20eh038_lb-lia-6 _cod_database_code 1557970 _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_estimated_absorpt_t_max 0.972 _shelx_estimated_absorpt_t_min 0.895 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All C(H,H,H) groups 2.a Aromatic/amide H refined with riding coordinates: C6(H6), C15(H15), C2(H2), C5(H5), C12(H12), C4(H4), C8(H8), C3(H3), C19(H19), C11(H11), C16(H16), C9(H9), C10(H10), C18(H18), C17(H17) 2.b Idealised Me refined as rotating group: C20(H20A,H20B,H20C), C21(H21A,H21B,H21C) ; _shelx_res_file ; 20eh038_lb-lia-6.res created by SHELXL-2014/7 TITL 20EH038_LB-LiA-6_a.res in P-1 REM Old TITL 20EH038_LB-LiA-6 in P-1 REM SHELXT solution in P-1 REM R1 0.189, Rweak 0.007, Alpha 0.030, Orientation as input REM Formula found by SHELXT: C3 Li N2 CELL 1.54184 9.5878 9.9347 9.9435 105.659 94.885 95.34 ZERR 1 0.0002 0.0002 0.0002 0.002 0.001 0.002 LATT 1 SFAC C H Li N O UNIT 42 42 2 4 2 L.S. 40 PLAN 4 SIZE 0.2 0.075 0.05 TEMP -100 MORE -1 BOND $H CONF fmap 2 acta OMIT -3 3 10 OMIT -3 4 9 REM REM REM WGHT 0.052300 0.171900 FVAR 9.14191 O1 5 0.260719 0.603763 0.372988 11.00000 0.03409 0.05096 = 0.04446 0.01461 0.01816 0.00808 N2 4 0.438565 0.685346 0.272781 11.00000 0.03144 0.03535 = 0.03679 0.00863 0.00962 0.00322 N1 4 0.102416 0.479657 0.624245 11.00000 0.03152 0.04443 = 0.03016 0.01590 0.00414 0.00706 C1 1 0.110680 0.579670 0.753036 11.00000 0.02086 0.04331 = 0.03400 0.01725 0.00586 0.00406 C13 1 0.358510 0.579845 0.298165 11.00000 0.02566 0.04108 = 0.03053 0.01236 0.00473 0.00382 C7 1 0.130611 0.341395 0.616720 11.00000 0.02722 0.04354 = 0.03089 0.01363 -0.00038 0.00343 C6 1 0.155870 0.562490 0.885747 11.00000 0.03164 0.04322 = 0.03429 0.01640 0.00577 0.01097 AFIX 43 H6 2 0.181500 0.473964 0.891567 11.00000 -1.20000 AFIX 0 C14 1 0.385028 0.431224 0.236701 11.00000 0.02919 0.03948 = 0.03529 0.01512 0.01098 0.00257 C15 1 0.275138 0.336655 0.151387 11.00000 0.03562 0.04401 = 0.03981 0.01295 0.00861 0.00021 AFIX 43 H15 2 0.188429 0.368623 0.127934 11.00000 -1.20000 AFIX 0 C2 1 0.075653 0.714840 0.753754 11.00000 0.03312 0.04642 = 0.03937 0.02170 0.00323 0.00580 AFIX 43 H2 2 0.044784 0.731783 0.667100 11.00000 -1.20000 AFIX 0 C5 1 0.163483 0.671957 1.007155 11.00000 0.04251 0.05409 = 0.03195 0.01569 0.00472 0.01285 AFIX 43 H5 2 0.193380 0.656323 1.094681 11.00000 -1.20000 AFIX 0 C12 1 0.214791 0.276372 0.515302 11.00000 0.03812 0.04893 = 0.03176 0.01292 0.00454 0.00592 AFIX 43 H12 2 0.256964 0.329253 0.459563 11.00000 -1.20000 AFIX 0 C20 1 0.536792 0.668430 0.166789 11.00000 0.03539 0.04316 = 0.04023 0.01390 0.01390 0.00130 AFIX 137 H20A 2 0.547763 0.568466 0.130300 11.00000 -1.50000 H20B 2 0.628537 0.721523 0.209248 11.00000 -1.50000 H20C 2 0.500051 0.703937 0.089628 11.00000 -1.50000 AFIX 0 C4 1 0.128980 0.803606 1.005401 11.00000 0.04677 0.04547 = 0.04117 0.00817 0.00714 0.00862 AFIX 43 H4 2 0.135286 0.878146 1.089690 11.00000 -1.20000 AFIX 0 C8 1 0.070132 0.257847 0.695261 11.00000 0.03474 0.04756 = 0.04386 0.01817 0.00835 0.00321 AFIX 43 H8 2 0.010811 0.297042 0.763714 11.00000 -1.20000 AFIX 0 C3 1 0.084794 0.822893 0.876005 11.00000 0.04097 0.04145 = 0.05253 0.01987 0.00723 0.00901 AFIX 43 H3 2 0.060406 0.912271 0.871680 11.00000 -1.20000 AFIX 0 C19 1 0.511511 0.383851 0.270637 11.00000 0.03246 0.04686 = 0.06222 0.02024 0.00766 0.00509 AFIX 43 H19 2 0.586868 0.448197 0.327923 11.00000 -1.20000 AFIX 0 C11 1 0.237879 0.137311 0.494483 11.00000 0.04820 0.04825 = 0.04415 0.00540 0.00580 0.00976 AFIX 43 H11 2 0.293984 0.095831 0.423797 11.00000 -1.20000 AFIX 0 C16 1 0.293127 0.196239 0.101197 11.00000 0.05342 0.04236 = 0.05318 0.00811 0.01584 -0.00525 AFIX 43 H16 2 0.218802 0.131865 0.042186 11.00000 -1.20000 AFIX 0 C21 1 0.411142 0.829121 0.336212 11.00000 0.04486 0.03715 = 0.05924 0.00561 0.01199 0.00551 AFIX 137 H21A 2 0.326812 0.848563 0.285204 11.00000 -1.50000 H21B 2 0.492131 0.894842 0.331395 11.00000 -1.50000 H21C 2 0.396021 0.840751 0.434739 11.00000 -1.50000 AFIX 0 C9 1 0.095594 0.119622 0.674483 11.00000 0.04890 0.04615 = 0.05837 0.02287 0.00857 -0.00091 AFIX 43 H9 2 0.053995 0.065649 0.729563 11.00000 -1.20000 AFIX 0 C10 1 0.180349 0.058055 0.575218 11.00000 0.05537 0.03982 = 0.06118 0.01144 0.00397 0.00497 AFIX 43 H10 2 0.198560 -0.036640 0.562877 11.00000 -1.20000 AFIX 0 C18 1 0.527474 0.242479 0.220705 11.00000 0.04519 0.05197 = 0.08916 0.03035 0.02216 0.01776 AFIX 43 H18 2 0.613627 0.209767 0.244580 11.00000 -1.20000 AFIX 0 C17 1 0.418300 0.148722 0.136135 11.00000 0.06354 0.03785 = 0.07599 0.01790 0.03443 0.00864 AFIX 43 H17 2 0.429477 0.051801 0.102171 11.00000 -1.20000 AFIX 0 LI1 3 0.110149 0.538271 0.448242 11.00000 0.03069 0.05119 = 0.03436 0.02020 0.00828 0.00665 HKLF 4 REM 20EH038_LB-LiA-6_a.res in P-1 REM R1 = 0.0393 for 3222 Fo > 4sig(Fo) and 0.0462 for all 3722 data REM 228 parameters refined using 0 restraints END WGHT 0.0523 0.1719 REM Highest difference peak 0.185, deepest hole -0.208, 1-sigma level 0.039 Q1 1 0.4059 0.8951 0.2584 11.00000 0.05 0.18 Q2 1 0.0826 0.4976 0.5434 11.00000 0.05 0.18 Q3 1 0.3064 0.8316 0.3664 11.00000 0.05 0.15 Q4 1 0.1012 0.5591 0.8228 11.00000 0.05 0.14 ; _shelx_res_checksum 37539 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -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 O1 O 0.26072(9) 0.60376(10) 0.37299(9) 0.0419(2) Uani 1 1 d . . . . . N2 N 0.43857(10) 0.68535(10) 0.27278(10) 0.0345(2) Uani 1 1 d . . . . . N1 N 0.10242(10) 0.47966(11) 0.62425(10) 0.0341(2) Uani 1 1 d . . . . . C1 C 0.11068(11) 0.57967(12) 0.75304(12) 0.0313(2) Uani 1 1 d . . . . . C13 C 0.35851(11) 0.57984(12) 0.29817(11) 0.0319(2) Uani 1 1 d . . . . . C7 C 0.13061(11) 0.34139(13) 0.61672(12) 0.0335(3) Uani 1 1 d . . . . . C6 C 0.15587(12) 0.56249(13) 0.88575(12) 0.0347(3) Uani 1 1 d . . . . . H6 H 0.1815 0.4740 0.8916 0.042 Uiso 1 1 calc R . . . . C14 C 0.38503(12) 0.43122(12) 0.23670(12) 0.0334(3) Uani 1 1 d . . . . . C15 C 0.27514(13) 0.33665(14) 0.15139(13) 0.0396(3) Uani 1 1 d . . . . . H15 H 0.1884 0.3686 0.1279 0.048 Uiso 1 1 calc R . . . . C2 C 0.07565(12) 0.71484(13) 0.75375(13) 0.0377(3) Uani 1 1 d . . . . . H2 H 0.0448 0.7318 0.6671 0.045 Uiso 1 1 calc R . . . . C5 C 0.16348(14) 0.67196(14) 1.00716(13) 0.0416(3) Uani 1 1 d . . . . . H5 H 0.1934 0.6563 1.0947 0.050 Uiso 1 1 calc R . . . . C12 C 0.21479(13) 0.27637(14) 0.51530(12) 0.0392(3) Uani 1 1 d . . . . . H12 H 0.2570 0.3293 0.4596 0.047 Uiso 1 1 calc R . . . . C20 C 0.53679(13) 0.66843(13) 0.16679(13) 0.0388(3) Uani 1 1 d . . . . . H20A H 0.5478 0.5685 0.1303 0.058 Uiso 1 1 calc GR . . . . H20B H 0.6285 0.7215 0.2092 0.058 Uiso 1 1 calc GR . . . . H20C H 0.5001 0.7039 0.0896 0.058 Uiso 1 1 calc GR . . . . C4 C 0.12898(15) 0.80361(15) 1.00540(14) 0.0449(3) Uani 1 1 d . . . . . H4 H 0.1353 0.8781 1.0897 0.054 Uiso 1 1 calc R . . . . C8 C 0.07013(13) 0.25785(14) 0.69526(14) 0.0409(3) Uani 1 1 d . . . . . H8 H 0.0108 0.2970 0.7637 0.049 Uiso 1 1 calc R . . . . C3 C 0.08479(14) 0.82289(14) 0.87601(15) 0.0433(3) Uani 1 1 d . . . . . H3 H 0.0604 0.9123 0.8717 0.052 Uiso 1 1 calc R . . . . C19 C 0.51151(14) 0.38385(15) 0.27064(16) 0.0460(3) Uani 1 1 d . . . . . H19 H 0.5869 0.4482 0.3279 0.055 Uiso 1 1 calc R . . . . C11 C 0.23788(15) 0.13731(15) 0.49448(15) 0.0481(3) Uani 1 1 d . . . . . H11 H 0.2940 0.0958 0.4238 0.058 Uiso 1 1 calc R . . . . C16 C 0.29313(16) 0.19624(15) 0.10120(16) 0.0508(3) Uani 1 1 d . . . . . H16 H 0.2188 0.1319 0.0422 0.061 Uiso 1 1 calc R . . . . C21 C 0.41114(15) 0.82912(14) 0.33621(16) 0.0482(3) Uani 1 1 d . . . . . H21A H 0.3268 0.8486 0.2852 0.072 Uiso 1 1 calc GR . . . . H21B H 0.4921 0.8948 0.3314 0.072 Uiso 1 1 calc GR . . . . H21C H 0.3960 0.8408 0.4347 0.072 Uiso 1 1 calc GR . . . . C9 C 0.09559(15) 0.11962(15) 0.67448(16) 0.0498(3) Uani 1 1 d . . . . . H9 H 0.0540 0.0656 0.7296 0.060 Uiso 1 1 calc R . . . . C10 C 0.18035(16) 0.05806(15) 0.57522(17) 0.0529(3) Uani 1 1 d . . . . . H10 H 0.1986 -0.0366 0.5629 0.063 Uiso 1 1 calc R . . . . C18 C 0.52747(16) 0.24248(16) 0.2207(2) 0.0584(4) Uani 1 1 d . . . . . H18 H 0.6136 0.2098 0.2446 0.070 Uiso 1 1 calc R . . . . C17 C 0.41830(17) 0.14872(15) 0.13613(18) 0.0570(4) Uani 1 1 d . . . . . H17 H 0.4295 0.0518 0.1022 0.068 Uiso 1 1 calc R . . . . Li1 Li 0.1101(2) 0.5383(2) 0.4482(2) 0.0367(4) Uani 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 O1 0.0341(4) 0.0510(5) 0.0445(5) 0.0146(4) 0.0182(4) 0.0081(4) N2 0.0314(5) 0.0353(5) 0.0368(5) 0.0086(4) 0.0096(4) 0.0032(4) N1 0.0315(5) 0.0444(5) 0.0302(5) 0.0159(4) 0.0041(4) 0.0071(4) C1 0.0209(5) 0.0433(6) 0.0340(6) 0.0173(5) 0.0059(4) 0.0041(4) C13 0.0257(5) 0.0411(6) 0.0305(5) 0.0124(5) 0.0047(4) 0.0038(4) C7 0.0272(5) 0.0435(6) 0.0309(5) 0.0136(5) -0.0004(4) 0.0034(4) C6 0.0316(5) 0.0432(6) 0.0343(6) 0.0164(5) 0.0058(4) 0.0110(5) C14 0.0292(5) 0.0395(6) 0.0353(6) 0.0151(5) 0.0110(4) 0.0026(4) C15 0.0356(6) 0.0440(7) 0.0398(6) 0.0129(5) 0.0086(5) 0.0002(5) C2 0.0331(6) 0.0464(7) 0.0394(6) 0.0217(5) 0.0032(5) 0.0058(5) C5 0.0425(7) 0.0541(8) 0.0320(6) 0.0157(5) 0.0047(5) 0.0129(6) C12 0.0381(6) 0.0489(7) 0.0318(6) 0.0129(5) 0.0045(5) 0.0059(5) C20 0.0354(6) 0.0432(7) 0.0402(6) 0.0139(5) 0.0139(5) 0.0013(5) C4 0.0468(7) 0.0455(7) 0.0412(7) 0.0082(5) 0.0071(5) 0.0086(6) C8 0.0347(6) 0.0476(7) 0.0439(7) 0.0182(6) 0.0084(5) 0.0032(5) C3 0.0410(7) 0.0414(7) 0.0525(7) 0.0199(6) 0.0072(5) 0.0090(5) C19 0.0325(6) 0.0469(7) 0.0622(8) 0.0202(6) 0.0077(6) 0.0051(5) C11 0.0482(7) 0.0482(7) 0.0442(7) 0.0054(6) 0.0058(6) 0.0098(6) C16 0.0534(8) 0.0424(7) 0.0532(8) 0.0081(6) 0.0158(6) -0.0053(6) C21 0.0449(7) 0.0372(7) 0.0592(8) 0.0056(6) 0.0120(6) 0.0055(5) C9 0.0489(8) 0.0461(7) 0.0584(8) 0.0229(6) 0.0086(6) -0.0009(6) C10 0.0554(8) 0.0398(7) 0.0612(9) 0.0114(6) 0.0040(7) 0.0050(6) C18 0.0452(8) 0.0520(8) 0.0892(12) 0.0303(8) 0.0222(8) 0.0178(7) C17 0.0635(9) 0.0379(7) 0.0760(10) 0.0179(7) 0.0344(8) 0.0086(6) Li1 0.0307(9) 0.0512(12) 0.0344(10) 0.0202(9) 0.0083(7) 0.0066(8) 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' Li Li 0.0008 0.0003 '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_ _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 C13 O1 Li1 149.60(11) . . ? C13 N2 C20 124.75(10) . . ? C13 N2 C21 118.69(10) . . ? C21 N2 C20 115.70(10) . . ? C1 N1 C7 120.48(9) . . ? C1 N1 Li1 120.42(10) . . ? C1 N1 Li1 101.84(9) . 2_566 ? C7 N1 Li1 116.46(9) . . ? C7 N1 Li1 105.37(9) . 2_566 ? Li1 N1 Li1 78.18(9) . 2_566 ? N1 C1 C6 126.57(11) . . ? N1 C1 C2 117.70(10) . . ? N1 C1 Li1 48.33(7) . 2_566 ? C6 C1 Li1 134.75(9) . 2_566 ? C2 C1 C6 115.69(11) . . ? C2 C1 Li1 89.66(8) . 2_566 ? O1 C13 N2 120.64(11) . . ? O1 C13 C14 119.20(10) . . ? N2 C13 C14 120.16(10) . . ? C12 C7 N1 118.46(10) . . ? C12 C7 C8 116.68(11) . . ? C8 C7 N1 124.60(11) . . ? C1 C6 H6 119.4 . . ? C5 C6 C1 121.24(11) . . ? C5 C6 H6 119.4 . . ? C15 C14 C13 118.26(10) . . ? C19 C14 C13 121.65(11) . . ? C19 C14 C15 119.92(12) . . ? C14 C15 H15 120.2 . . ? C16 C15 C14 119.62(12) . . ? C16 C15 H15 120.2 . . ? C1 C2 H2 118.9 . . ? C3 C2 C1 122.15(11) . . ? C3 C2 H2 118.9 . . ? C6 C5 H5 118.9 . . ? C6 C5 C4 122.10(11) . . ? C4 C5 H5 118.9 . . ? C7 C12 H12 119.2 . . ? C11 C12 C7 121.65(12) . . ? C11 C12 H12 119.2 . . ? N2 C20 H20A 109.5 . . ? N2 C20 H20B 109.5 . . ? N2 C20 H20C 109.5 . . ? H20A C20 H20B 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C5 C4 H4 121.2 . . ? C5 C4 C3 117.59(12) . . ? C3 C4 H4 121.2 . . ? C7 C8 H8 119.5 . . ? C9 C8 C7 120.99(12) . . ? C9 C8 H8 119.5 . . ? C2 C3 C4 121.23(12) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? C14 C19 H19 120.1 . . ? C18 C19 C14 119.80(13) . . ? C18 C19 H19 120.1 . . ? C12 C11 H11 119.6 . . ? C10 C11 C12 120.75(13) . . ? C10 C11 H11 119.6 . . ? C15 C16 H16 119.7 . . ? C17 C16 C15 120.52(14) . . ? C17 C16 H16 119.7 . . ? N2 C21 H21A 109.5 . . ? N2 C21 H21B 109.5 . . ? N2 C21 H21C 109.5 . . ? H21A C21 H21B 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C8 C9 H9 119.3 . . ? C8 C9 C10 121.41(13) . . ? C10 C9 H9 119.3 . . ? C11 C10 C9 118.48(13) . . ? C11 C10 H10 120.8 . . ? C9 C10 H10 120.8 . . ? C19 C18 H18 119.9 . . ? C17 C18 C19 120.22(14) . . ? C17 C18 H18 119.9 . . ? C16 C17 C18 119.92(13) . . ? C16 C17 H17 120.0 . . ? C18 C17 H17 120.0 . . ? O1 Li1 N1 127.70(11) . 2_566 ? O1 Li1 N1 130.34(11) . . ? O1 Li1 C1 111.33(9) . 2_566 ? O1 Li1 Li1 175.82(16) . 2_566 ? N1 Li1 N1 101.82(9) . 2_566 ? N1 Li1 C1 29.83(5) 2_566 2_566 ? N1 Li1 C1 114.44(9) . 2_566 ? N1 Li1 Li1 49.44(7) 2_566 2_566 ? N1 Li1 Li1 52.38(7) . 2_566 ? Li1 Li1 C1 67.61(9) 2_566 2_566 ? 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 O1 C13 1.2466(14) . ? O1 Li1 1.827(2) . ? N2 C13 1.3332(15) . ? N2 C20 1.4591(14) . ? N2 C21 1.4557(16) . ? N1 C1 1.3837(15) . ? N1 C7 1.4080(15) . ? N1 Li1 1.993(2) . ? N1 Li1 2.078(2) 2_566 ? C1 C6 1.4129(15) . ? C1 C2 1.4126(16) . ? C1 Li1 2.723(2) 2_566 ? C13 C14 1.4925(16) . ? C7 C12 1.4035(17) . ? C7 C8 1.4045(17) . ? C6 H6 0.9500 . ? C6 C5 1.3809(18) . ? C14 C15 1.3949(17) . ? C14 C19 1.3886(17) . ? C15 H15 0.9500 . ? C15 C16 1.3815(19) . ? C2 H2 0.9500 . ? C2 C3 1.3775(19) . ? C5 H5 0.9500 . ? C5 C4 1.3828(18) . ? C12 H12 0.9500 . ? C12 C11 1.3823(18) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C4 H4 0.9500 . ? C4 C3 1.3882(19) . ? C8 H8 0.9500 . ? C8 C9 1.3805(19) . ? C3 H3 0.9500 . ? C19 H19 0.9500 . ? C19 C18 1.385(2) . ? C11 H11 0.9500 . ? C11 C10 1.380(2) . ? C16 H16 0.9500 . ? C16 C17 1.381(2) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C9 H9 0.9500 . ? C9 C10 1.383(2) . ? C10 H10 0.9500 . ? C18 H18 0.9500 . ? C18 C17 1.384(2) . ? C17 H17 0.9500 . ? Li1 N1 2.078(2) 2_566 ? Li1 C1 2.722(2) 2_566 ? Li1 Li1 2.568(4) 2_566 ? 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 O1 C13 C14 C15 57.49(15) . . . . ? O1 C13 C14 C19 -117.78(13) . . . . ? N2 C13 C14 C15 -122.37(12) . . . . ? N2 C13 C14 C19 62.36(16) . . . . ? N1 C1 C6 C5 178.08(11) . . . . ? N1 C1 C2 C3 -177.91(11) . . . . ? N1 C7 C12 C11 -174.91(11) . . . . ? N1 C7 C8 C9 175.34(11) . . . . ? C1 N1 C7 C12 -135.94(11) . . . . ? C1 N1 C7 C8 50.10(16) . . . . ? C1 C6 C5 C4 -0.66(19) . . . . ? C1 C2 C3 C4 -0.15(19) . . . . ? C13 O1 Li1 N1 -98.3(2) . . . 2_566 ? C13 O1 Li1 N1 86.8(3) . . . . ? C13 O1 Li1 C1 -69.3(2) . . . 2_566 ? C13 C14 C15 C16 -175.37(11) . . . . ? C13 C14 C19 C18 174.55(12) . . . . ? C7 N1 C1 C6 4.93(17) . . . . ? C7 N1 C1 C2 -177.51(10) . . . . ? C7 N1 C1 Li1 -115.95(12) . . . 2_566 ? C7 C12 C11 C10 -1.2(2) . . . . ? C7 C8 C9 C10 -0.5(2) . . . . ? C6 C1 C2 C3 -0.08(17) . . . . ? C6 C5 C4 C3 0.4(2) . . . . ? C14 C15 C16 C17 0.7(2) . . . . ? C14 C19 C18 C17 0.6(2) . . . . ? C15 C14 C19 C18 -0.65(19) . . . . ? C15 C16 C17 C18 -0.8(2) . . . . ? C2 C1 C6 C5 0.47(17) . . . . ? C5 C4 C3 C2 0.0(2) . . . . ? C12 C7 C8 C9 1.29(18) . . . . ? C12 C11 C10 C9 1.9(2) . . . . ? C20 N2 C13 O1 -167.79(11) . . . . ? C20 N2 C13 C14 12.07(17) . . . . ? C8 C7 C12 C11 -0.47(18) . . . . ? C8 C9 C10 C11 -1.1(2) . . . . ? C19 C14 C15 C16 -0.01(18) . . . . ? C19 C18 C17 C16 0.1(2) . . . . ? C21 N2 C13 O1 1.09(17) . . . . ? C21 N2 C13 C14 -179.05(11) . . . . ? Li1 O1 C13 N2 174.92(17) . . . . ? Li1 O1 C13 C14 -4.9(3) . . . . ? Li1 N1 C1 C6 -155.99(11) . . . . ? Li1 N1 C1 C6 120.88(12) 2_566 . . . ? Li1 N1 C1 C2 -61.56(12) 2_566 . . . ? Li1 N1 C1 C2 21.56(15) . . . . ? Li1 N1 C1 Li1 83.13(11) . . . 2_566 ? Li1 N1 C7 C12 109.95(11) 2_566 . . . ? Li1 N1 C7 C12 25.71(14) . . . . ? Li1 N1 C7 C8 -64.01(13) 2_566 . . . ? Li1 N1 C7 C8 -148.25(12) . . . . ? Li1 C1 C6 C5 -117.40(14) 2_566 . . . ? Li1 C1 C2 C3 141.03(12) 2_566 . . . ?